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Acta Cryst. (2000). B56, 1071-1079
https://doi.org/10.1107/S010876810001154X
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Crystal engineering in the gem-alkynol family; synthon repetitivity and topological similarity in diphenylethynylmethanols: structures that lack O—­H...O hydrogen bonds

C. Bilton, J. A. K. Howard, N. N. L. Madhavi, A. Nangia, G. R. Desiraju, F. H. Allen and C. C. Wilson
The structures of four para-substituted derivatives of diphenylethynylmethanol have been determined [ditolylethynylmethanol, di(4-chlorophenyl)ethynylmethanol, di(4-bromophenyl)ethynylmethanol and bis(4,4′-biphenylyl)ethynylmethanol]. The dimethyl, dichloro, dibromo and diphenyl compounds have been analysed using X-ray diffraction at 150 K, and the dichloro compound has also been studied using neutron diffraction at 150 K. In common with the parent diphenylethynylmethanol [Garcia, Ramos, ­Rodriguez & Fronczek (1995). Acta Cryst. C51, 2674–2676], all four derivatives fail to form the expected strong O—H...O hydrogen bonds due to steric hindrance. Instead, the supramolecular structural organization in this family of gem-alkynols is mediated by a variety of weaker interactions. The two most acidic protons, O—H and C[triple bond]C—H, participate in weak hydrogen bonds to π-acceptors, forming synthons that stabilize all five structures. These primary interactions are reinforced by a variety of other weak hydrogen bonds involving C—H donors and the hydroxy-O as an acceptor, and by halogen...halogen interactions in the dichloro and dibromo compounds.
Keywords: gem-Alkynol; Synthon repetitivity; Topological similarity.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810001154X/bm0034sup1.cif
Contains datablocks global, 2, 3X, 3N, 4, 5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00342sup2.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00343Xsup3.hkl
Contains datablock 3X

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00343Nsup4.hkl
Contains datablock 3N

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00344sup5.hkl
Contains datablock 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810001154X/bm00345sup6.hkl
Contains datablock 5

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S010876810001154X/bm0034sup7.pdf
Supplementary material

CCDC references: 156670; 156671; 156672; 156673; 156674

Computing details top

Data collection: Bruker SMART (Bruker Systems Inc., 1999a) for (2), (3X), (4), (5); SXD (Keen & Wilson, 1996) for (3N). Cell refinement: Bruker SMART (Bruker Systems Inc., 1999a) for (2), (3X), (4), (5); SXD (Keen & Wilson, 1996) for (3N). Data reduction: Bruker SAINT (Bruker Systems Inc., 1999b) for (2), (3X), (4), (5); SXD (Keen & Wilson, 1996) for (3N). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(2) top
Crystal data top
C17H16OF(000) = 252
Mr = 236.30Dx = 1.204 Mg m−3
Triclinic, P1Melting point: 95-96 K
a = 6.8286 (14) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.2407 (16) ÅCell parameters from 512 reflections
c = 12.658 (3) Åθ = 5.3–29.4°
α = 106.73 (3)°µ = 0.07 mm−1
β = 98.71 (3)°T = 150 K
γ = 101.39 (3)°Block, colourless
V = 652.0 (2) Å30.3 × 0.3 × 0.2 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer		2964 independent reflections
Radiation source: fine-focus sealed tube2362 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
SADABS (Sheldrick 1996)		h = −8→8
Tmin = 0.784, Tmax = 1.000k = −10→7
4775 measured reflectionsl = −14→16
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: difference Fourier map
wR(F2) = 0.132All H-atom parameters refined
S = 1.03 w = 1/[σ2(Fo2) + (0.0618P)2 + 0.2678P]
where P = (Fo2 + 2Fc2)/3
2964 reflections(Δ/σ)max = 0.028
231 parametersΔρmax = 0.21 e Å−3
0 restraintsΔρmin = −0.20 e Å−3
Crystal data top
C17H16Oγ = 101.39 (3)°
Mr = 236.30V = 652.0 (2) Å3
Triclinic, P1Z = 2
a = 6.8286 (14) ÅMo Kα radiation
b = 8.2407 (16) ŵ = 0.07 mm−1
c = 12.658 (3) ÅT = 150 K
α = 106.73 (3)°0.3 × 0.3 × 0.2 mm
β = 98.71 (3)°
Data collection top
Bruker SMART CCD
diffractometer		2964 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick 1996)		2362 reflections with I > 2σ(I)
Tmin = 0.784, Tmax = 1.000Rint = 0.018
4775 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.132All H-atom parameters refined
S = 1.03Δρmax = 0.21 e Å−3
2964 reflectionsΔρmin = −0.20 e Å−3
231 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
H10.759 (3)−0.095 (3)0.3239 (19)0.052 (6)*
C10.7141 (3)−0.0109 (2)0.29487 (14)0.0344 (4)
C20.6603 (2)0.09261 (19)0.25638 (13)0.0266 (3)
C30.5790 (2)0.21385 (18)0.20481 (12)0.0229 (3)
O10.36138 (16)0.14659 (15)0.16398 (10)0.0278 (3)
HA0.348 (4)0.043 (3)0.119 (2)0.060 (7)*
C40.6155 (2)0.39365 (18)0.29666 (12)0.0224 (3)
C50.4550 (2)0.4686 (2)0.31962 (14)0.0277 (3)
H50.314 (3)0.409 (3)0.2785 (18)0.044 (6)*
C60.4927 (3)0.6303 (2)0.40489 (14)0.0303 (4)
H60.378 (3)0.683 (3)0.4221 (16)0.039 (5)*
C70.6903 (2)0.71997 (19)0.46824 (12)0.0263 (3)
C80.7306 (3)0.8924 (2)0.56227 (15)0.0356 (4)
H8A0.837 (4)0.987 (4)0.554 (2)0.077 (8)*
H8B0.606 (5)0.934 (4)0.570 (2)0.088 (9)*
H8C0.783 (4)0.882 (4)0.636 (2)0.077 (8)*
C90.8508 (2)0.6444 (2)0.44306 (13)0.0281 (3)
H90.990 (3)0.702 (2)0.4848 (16)0.032 (5)*
C100.8142 (2)0.4830 (2)0.35843 (13)0.0272 (3)
H100.932 (3)0.432 (3)0.3424 (17)0.043 (5)*
C110.6815 (2)0.23500 (17)0.10758 (12)0.0222 (3)
C120.5842 (2)0.29838 (19)0.02815 (13)0.0260 (3)
H120.453 (3)0.324 (2)0.0344 (16)0.034 (5)*
C130.6724 (3)0.3212 (2)−0.06040 (13)0.0282 (3)
H130.601 (3)0.361 (3)−0.1146 (18)0.044 (6)*
C140.8597 (2)0.28299 (18)−0.07268 (13)0.0266 (3)
C150.9529 (3)0.3045 (2)−0.17029 (15)0.0362 (4)
H15A1.010 (7)0.206 (6)−0.202 (4)0.045 (11)*0.50
H661.112 (7)0.323 (6)−0.152 (4)0.043 (11)*0.50
H15B0.994 (5)0.421 (4)−0.168 (3)0.095 (10)*
H15C0.854 (5)0.250 (4)−0.241 (3)0.090 (9)*
C160.9569 (2)0.22143 (19)0.00761 (13)0.0266 (3)
H161.086 (3)0.192 (2)0.0026 (16)0.031 (5)*
C170.8691 (2)0.19732 (19)0.09667 (13)0.0248 (3)
H170.939 (3)0.152 (2)0.1506 (15)0.027 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0441 (10)0.0283 (8)0.0350 (9)0.0110 (7)0.0101 (7)0.0148 (7)
C20.0292 (8)0.0220 (7)0.0261 (7)0.0033 (6)0.0066 (6)0.0061 (6)
C30.0223 (7)0.0198 (7)0.0249 (7)0.0039 (5)0.0031 (5)0.0065 (6)
O10.0227 (5)0.0230 (5)0.0319 (6)0.0013 (4)0.0030 (4)0.0050 (5)
C40.0269 (7)0.0197 (6)0.0215 (7)0.0053 (5)0.0056 (5)0.0084 (5)
C50.0243 (8)0.0247 (7)0.0314 (8)0.0051 (6)0.0039 (6)0.0072 (6)
C60.0307 (8)0.0263 (8)0.0356 (9)0.0111 (6)0.0101 (7)0.0088 (7)
C70.0351 (8)0.0216 (7)0.0229 (7)0.0057 (6)0.0082 (6)0.0088 (6)
C80.0460 (10)0.0252 (8)0.0309 (9)0.0070 (7)0.0106 (7)0.0026 (7)
C90.0279 (8)0.0263 (7)0.0253 (7)0.0019 (6)0.0023 (6)0.0064 (6)
C100.0253 (8)0.0253 (7)0.0294 (8)0.0066 (6)0.0060 (6)0.0063 (6)
C110.0239 (7)0.0161 (6)0.0227 (7)0.0028 (5)0.0027 (5)0.0035 (5)
C120.0253 (8)0.0237 (7)0.0284 (8)0.0073 (6)0.0033 (6)0.0081 (6)
C130.0341 (8)0.0240 (7)0.0252 (7)0.0070 (6)0.0018 (6)0.0087 (6)
C140.0328 (8)0.0172 (6)0.0243 (7)0.0007 (6)0.0068 (6)0.0020 (5)
C150.0494 (11)0.0275 (8)0.0296 (9)0.0053 (8)0.0157 (8)0.0055 (7)
C160.0243 (7)0.0218 (7)0.0313 (8)0.0056 (6)0.0066 (6)0.0051 (6)
C170.0254 (7)0.0205 (7)0.0262 (7)0.0053 (6)0.0024 (6)0.0063 (6)
Geometric parameters (Å, º) top
C1—C21.187 (2)C9—C101.395 (2)
C1—H10.95 (2)C9—H90.97 (2)
C2—C31.489 (2)C10—H101.00 (2)
C3—O11.4349 (18)C11—C171.394 (2)
C3—C111.540 (2)C11—C121.401 (2)
C3—C41.544 (2)C12—C131.391 (2)
O1—HA0.85 (3)C12—H120.97 (2)
C4—C51.389 (2)C13—C141.396 (2)
C4—C101.395 (2)C13—H130.95 (2)
C5—C61.400 (2)C14—C161.399 (2)
C5—H50.98 (2)C14—C151.511 (2)
C6—C71.395 (2)C15—H15A0.98 (4)
C6—H60.99 (2)C15—H661.04 (5)
C7—C91.397 (2)C15—H15B0.94 (3)
C7—C81.511 (2)C15—H15C0.97 (3)
C8—H8A0.99 (3)C16—C171.399 (2)
C8—H8B0.98 (3)C16—H160.965 (19)
C8—H8C0.99 (3)C17—H170.974 (18)
C2—C1—H1178.4 (14)C9—C10—H10119.2 (12)
C1—C2—C3176.11 (17)C4—C10—H10120.3 (12)
O1—C3—C2108.99 (12)C17—C11—C12118.62 (14)
O1—C3—C11110.27 (12)C17—C11—C3122.77 (13)
C2—C3—C11111.00 (12)C12—C11—C3118.59 (13)
O1—C3—C4106.89 (12)C13—C12—C11120.51 (14)
C2—C3—C4109.38 (12)C13—C12—H12120.2 (11)
C11—C3—C4110.21 (11)C11—C12—H12119.3 (11)
C3—O1—HA103.8 (17)C12—C13—C14121.45 (14)
C5—C4—C10119.09 (14)C12—C13—H13118.9 (13)
C5—C4—C3121.53 (13)C14—C13—H13119.7 (13)
C10—C4—C3119.38 (13)C13—C14—C16117.71 (14)
C4—C5—C6120.15 (15)C13—C14—C15121.28 (15)
C4—C5—H5121.1 (12)C16—C14—C15121.01 (15)
C6—C5—H5118.8 (12)C14—C15—H15A111 (3)
C7—C6—C5121.34 (15)C14—C15—H66112 (2)
C7—C6—H6118.3 (12)H15A—C15—H6661 (3)
C5—C6—H6120.3 (12)C14—C15—H15B114.0 (19)
C6—C7—C9117.91 (14)H15A—C15—H15B129 (3)
C6—C7—C8121.42 (15)H66—C15—H15B81 (3)
C9—C7—C8120.66 (15)C14—C15—H15C111.2 (19)
C7—C8—H8A113.0 (16)H15A—C15—H15C82 (3)
C7—C8—H8B113.1 (18)H66—C15—H15C130 (3)
H8A—C8—H8B109 (2)H15B—C15—H15C102 (3)
C7—C8—H8C111.0 (16)C14—C16—C17121.30 (14)
H8A—C8—H8C105 (2)C14—C16—H16121.2 (11)
H8B—C8—H8C105 (2)C17—C16—H16117.5 (11)
C10—C9—C7121.05 (15)C11—C17—C16120.41 (14)
C10—C9—H9118.2 (11)C11—C17—H17119.9 (11)
C7—C9—H9120.7 (11)C16—C17—H17119.7 (11)
C9—C10—C4120.45 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HA···C11i0.85 (3)3.07 (3)3.860 (2)155 (2)
O1—HA···C13i0.85 (3)2.85 (3)3.644 (2)156 (2)
O1—HA···C16i0.85 (3)2.61 (3)3.288 (2)137 (2)
Symmetry code: (i) −x+1, −y, −z.
(3X) top
Crystal data top
C15H10Cl2OF(000) = 284
Mr = 277.13Dx = 1.439 Mg m−3
Triclinic, P1Melting point: 72-73 K
a = 5.7082 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.3645 (2) ÅCell parameters from 500 reflections
c = 11.5167 (1) Åθ = 5.4–29.2°
α = 117.268 (1)°µ = 0.49 mm−1
β = 99.257 (1)°T = 150 K
γ = 96.726 (1)°Block, colourless
V = 639.73 (2) Å30.5 × 0.4 × 0.4 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer		2826 independent reflections
Radiation source: fine-focus sealed tube2617 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: not relevant pixels mm-1θmax = 27.3°, θmin = 2.1°
ω scansh = −6→7
Absorption correction: multi-scan
SADABS (Sheldrick 1996)		k = −11→14
Tmin = 0.284, Tmax = 0.332l = −14→12
4371 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: difference Fourier map
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.3533P]
where P = (Fo2 + 2Fc2)/3
2826 reflections(Δ/σ)max < 0.001
203 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.35 e Å−3
Crystal data top
C15H10Cl2Oγ = 96.726 (1)°
Mr = 277.13V = 639.73 (2) Å3
Triclinic, P1Z = 2
a = 5.7082 (1) ÅMo Kα radiation
b = 11.3645 (2) ŵ = 0.49 mm−1
c = 11.5167 (1) ÅT = 150 K
α = 117.268 (1)°0.5 × 0.4 × 0.4 mm
β = 99.257 (1)°
Data collection top
Bruker SMART CCD
diffractometer		2826 independent reflections
Absorption correction: multi-scan
SADABS (Sheldrick 1996)		2617 reflections with I > 2σ(I)
Tmin = 0.284, Tmax = 0.332Rint = 0.043
4371 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.104H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.33 e Å−3
2826 reflectionsΔρmin = −0.35 e Å−3
203 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H11.044 (5)−0.109 (3)0.266 (3)0.051 (7)*
C11.0066 (3)−0.02664 (17)0.30273 (19)0.0305 (4)
C20.9579 (3)0.08150 (16)0.35028 (16)0.0235 (3)
C30.9001 (3)0.21751 (15)0.40912 (16)0.0214 (3)
O11.1132 (2)0.31881 (11)0.44629 (13)0.0267 (3)
HA1.163 (5)0.298 (2)0.383 (3)0.040 (6)*
C40.8200 (3)0.24719 (14)0.53893 (15)0.0201 (3)
C50.9651 (3)0.34161 (15)0.66530 (16)0.0243 (3)
H51.126 (4)0.391 (2)0.673 (2)0.035 (5)*
C60.8855 (3)0.36662 (16)0.78075 (17)0.0270 (3)
H60.986 (4)0.430 (2)0.867 (2)0.029 (5)*
C70.6591 (3)0.29600 (16)0.76799 (16)0.0249 (3)
Cl10.04963 (8)0.26483 (5)0.05839 (5)0.03706 (14)
C80.5132 (3)0.20033 (17)0.64306 (17)0.0272 (3)
H80.357 (4)0.147 (2)0.632 (2)0.040 (6)*
C90.5949 (3)0.17631 (17)0.52931 (16)0.0252 (3)
H90.494 (4)0.110 (2)0.444 (2)0.036 (6)*
C100.6949 (3)0.22598 (15)0.31106 (15)0.0214 (3)
C110.6523 (3)0.35366 (15)0.33946 (17)0.0253 (3)
H110.751 (4)0.432 (2)0.414 (2)0.026 (5)*
C120.4577 (3)0.36638 (17)0.26036 (17)0.0276 (3)
H120.435 (4)0.455 (2)0.279 (2)0.036 (6)*
C130.3042 (3)0.25021 (17)0.15251 (16)0.0271 (3)
Cl20.55431 (8)0.32701 (5)0.91110 (4)0.03824 (15)
C140.3448 (3)0.12307 (17)0.12157 (17)0.0291 (3)
H140.247 (4)0.048 (2)0.050 (2)0.036 (6)*
C150.5417 (3)0.11124 (16)0.20127 (17)0.0264 (3)
H150.566 (4)0.025 (2)0.179 (2)0.029 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0236 (7)0.0274 (8)0.0405 (9)0.0084 (6)0.0108 (7)0.0149 (7)
C20.0164 (6)0.0271 (7)0.0270 (8)0.0029 (5)0.0064 (5)0.0134 (6)
C30.0176 (6)0.0196 (6)0.0249 (7)0.0004 (5)0.0058 (5)0.0097 (6)
O10.0208 (5)0.0248 (5)0.0316 (6)−0.0018 (4)0.0099 (5)0.0119 (5)
C40.0175 (6)0.0192 (6)0.0254 (7)0.0048 (5)0.0062 (5)0.0118 (6)
C50.0210 (7)0.0214 (7)0.0271 (8)0.0016 (5)0.0041 (6)0.0103 (6)
C60.0289 (8)0.0225 (7)0.0246 (8)0.0046 (6)0.0040 (6)0.0083 (6)
C70.0259 (7)0.0293 (7)0.0255 (7)0.0139 (6)0.0103 (6)0.0153 (6)
Cl10.0344 (2)0.0452 (3)0.0350 (2)0.01327 (19)0.00330 (18)0.0229 (2)
C80.0186 (7)0.0352 (8)0.0312 (9)0.0057 (6)0.0075 (6)0.0185 (7)
C90.0175 (7)0.0299 (8)0.0253 (8)0.0006 (6)0.0035 (6)0.0124 (6)
C100.0208 (7)0.0216 (7)0.0230 (7)0.0034 (5)0.0082 (5)0.0111 (6)
C110.0268 (7)0.0205 (7)0.0280 (8)0.0027 (6)0.0074 (6)0.0115 (6)
C120.0301 (8)0.0252 (7)0.0330 (8)0.0078 (6)0.0103 (7)0.0176 (7)
C130.0259 (7)0.0359 (8)0.0252 (8)0.0090 (6)0.0086 (6)0.0184 (7)
Cl20.0370 (2)0.0542 (3)0.0297 (2)0.0189 (2)0.01751 (18)0.0204 (2)
C140.0290 (8)0.0283 (8)0.0237 (8)0.0047 (6)0.0034 (6)0.0087 (7)
C150.0275 (8)0.0222 (7)0.0265 (8)0.0054 (6)0.0060 (6)0.0095 (6)
Geometric parameters (Å, º) top
C1—C21.183 (2)Cl1—C131.7404 (17)
C1—H10.90 (3)C8—C91.381 (2)
C2—C31.479 (2)C8—H80.97 (2)
C3—O11.4287 (17)C9—H90.95 (2)
C3—C41.534 (2)C10—C151.389 (2)
C3—C101.535 (2)C10—C111.395 (2)
O1—HA0.77 (3)C11—C121.385 (2)
C4—C51.389 (2)C11—H110.93 (2)
C4—C91.394 (2)C12—C131.389 (2)
C5—C61.391 (2)C12—H120.95 (2)
C5—H50.99 (2)C13—C141.379 (2)
C6—C71.387 (2)C14—C151.393 (2)
C6—H60.95 (2)C14—H140.90 (2)
C7—C81.384 (2)C15—H150.93 (2)
C7—Cl21.7415 (16)
C2—C1—H1179.0 (17)C7—C8—H8122.6 (14)
C1—C2—C3179.12 (17)C8—C9—C4120.99 (15)
O1—C3—C2109.98 (12)C8—C9—H9118.5 (14)
O1—C3—C4106.71 (12)C4—C9—H9120.5 (13)
C2—C3—C4109.22 (12)C15—C10—C11119.32 (15)
O1—C3—C10110.68 (12)C15—C10—C3122.36 (13)
C2—C3—C10111.25 (12)C11—C10—C3118.18 (13)
C4—C3—C10108.87 (12)C12—C11—C10120.56 (15)
C3—O1—HA106.2 (19)C12—C11—H11118.5 (12)
C5—C4—C9119.18 (14)C10—C11—H11121.0 (12)
C5—C4—C3122.08 (13)C11—C12—C13119.19 (15)
C9—C4—C3118.74 (13)C11—C12—H12119.5 (14)
C4—C5—C6120.45 (14)C13—C12—H12121.3 (14)
C4—C5—H5119.4 (13)C14—C13—C12121.21 (15)
C6—C5—H5120.2 (13)C14—C13—Cl1119.30 (13)
C7—C6—C5119.10 (15)C12—C13—Cl1119.45 (13)
C7—C6—H6120.6 (12)C13—C14—C15119.21 (15)
C5—C6—H6120.3 (13)C13—C14—H14120.6 (14)
C8—C7—C6121.27 (15)C15—C14—H14120.1 (14)
C8—C7—Cl2118.85 (12)C10—C15—C14120.50 (15)
C6—C7—Cl2119.88 (13)C10—C15—H15121.5 (13)
C9—C8—C7119.00 (15)C14—C15—H15118.0 (13)
C9—C8—H8118.4 (14)
(3N) top
Crystal data top
C15H10Cl2OZ = 2
Mr = 277.13F(000) = 284
Triclinic, P1Dx = 1.433 Mg m−3
a = 5.7280 (1) ÅMelting point: 72-73 K
b = 11.3620 (2) ÅNeutron radiation, λ = 0.5-5.0 Å
c = 11.5210 (1) ÅCell parameters from 25 reflections
α = 117.240 (1)°µ = 1.45 at 1 angstrom mm−1
β = 99.250 (1)°T = 150 K
γ = 96.860 (1)°Block, colourless
V = 641.87 (2) Å32.5 × 1.5 × 1.0 mm
Data collection top
SXD
diffractometer		2929 independent reflections
Radiation source: ISIS spallation source2928 reflections with I > 2σ(I)
None monochromatorRint = 0.062
time–of–flight LAUE diffraction scansθmax = 16.2°, θmin = 1.3°
Absorption correction: empirical (using intensity measurements)
The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.64 + 0.81 * lambda [cm-1]		h = 0→12
Tmin = 0.51, Tmax = 0.89k = −20→21
10674 measured reflectionsl = −19→10
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: difference Fourier map
wR(F2) = 0.128All H-atom parameters refined
S = 5.44 w = 1/[σ2(Fo2)]
2929 reflections(Δ/σ)max < 0.001
253 parametersExtinction correction: Becker-Coppens Lorentzian model
0 restraintsExtinction coefficient: 0.296
Crystal data top
C15H10Cl2Oγ = 96.860 (1)°
Mr = 277.13V = 641.87 (2) Å3
Triclinic, P1Z = 2
a = 5.7280 (1) ÅNeutron radiation, λ = 0.5-5.0 Å
b = 11.3620 (2) ŵ = 1.45 at 1 angstrom mm−1
c = 11.5210 (1) ÅT = 150 K
α = 117.240 (1)°2.5 × 1.5 × 1.0 mm
β = 99.250 (1)°
Data collection top
SXD
diffractometer		2929 independent reflections
Absorption correction: empirical (using intensity measurements)
The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.64 + 0.81 * lambda [cm-1]		2928 reflections with I > 2σ(I)
Tmin = 0.51, Tmax = 0.89Rint = 0.062
10674 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.067253 parameters
wR(F2) = 0.1280 restraints
S = 5.44All H-atom parameters refined
2929 reflections
Special details top

Experimental. For peak integration a local UB matrix refined for each frame, using approximately 25 reflections. Hence _cell_measurement_reflns_used 25

For final cell dimensions an average of all local cells was performed and estimated standard uncertainties were obtained from the spread of the local observations

Because of the nature of the experiment, it is not possible to give values of theta_min and theta_max for the cell determination. Instead, we can give values of

cell_measurement_sin(theta)/lambda_min 0.17 cell_measurement_sin(theta)/lambda_max 0.77

The same applies for the wavelength used for the experiment. The range of wavelengths used was 0.5-5.0 Angstroms, BUT the bulk of the diffraction information is obtained from wavelengths in the range 0.7-2.5 Angstroms.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The variable wavelength nature of the data collection procedure means that sensible values of _diffrn_reflns_theta_min & _diffrn_reflns_theta_max cannot be given It is also difficult to estimate realistic values of maximum sin(theta)/lambda values for two reasons: (i) Different sin(theta)/lambda ranges are accessed in different parts of the detectors (ii) The nature of the data collection occasionally allows some reflections at very high sin(theta)/lambda to be observed even when no real attempt has been made to measure data in this region. However, we can attempt to estimate the sin(theta)/lambda limits as follows:

diffrn_reflns_sin(theta)/lambda_min 0.087 diffrn_reflns_sin(theta)/lambda_max 1.116

Note also that reflections for which the standard profile fitting integration procedure fails are excluded from the data set, thus resulting in a high elimination rate of very weak or "unobserved" peaks from the final data set.

The extinction coefficient reported in _refine_ls_extinction_coef is in this case the refined value of the mosaic spread in units of 10-4 rad-1 The reference for the extinction method used is: Becker, P. & Coppens, P. (1974). Acta Cryst. A30, 129-148.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C11.0047 (4)−0.02661 (18)0.3033 (2)0.0333 (5)
C20.9559 (3)0.08311 (16)0.35113 (19)0.0223 (4)
C30.8984 (3)0.21786 (15)0.40894 (17)0.0187 (3)
O11.1102 (4)0.3181 (2)0.4452 (3)0.0268 (5)
C40.8194 (3)0.24703 (14)0.53838 (16)0.0171 (3)
C50.9649 (3)0.34106 (16)0.66423 (18)0.0236 (4)
C60.8860 (4)0.36646 (17)0.78000 (19)0.0269 (4)
C70.6603 (3)0.29618 (17)0.76792 (18)0.0236 (4)
Cl10.0542 (3)0.26511 (16)0.05897 (17)0.0421 (4)
C80.5148 (4)0.2012 (2)0.6435 (2)0.0278 (4)
C90.5950 (3)0.17659 (18)0.52866 (19)0.0247 (4)
C100.6940 (3)0.22635 (15)0.31199 (17)0.0193 (3)
C110.6513 (4)0.35329 (16)0.34004 (19)0.0248 (4)
C120.4579 (4)0.36662 (18)0.2611 (2)0.0282 (4)
C130.3053 (4)0.25032 (18)0.15295 (19)0.0266 (4)
Cl20.5579 (3)0.32699 (17)0.91032 (17)0.0434 (4)
C140.3467 (4)0.12323 (18)0.1226 (2)0.0299 (4)
C150.5422 (4)0.11157 (17)0.20187 (19)0.0265 (4)
H110.7679 (9)0.4433 (4)0.4257 (5)0.0482 (12)
H150.5713 (10)0.0116 (4)0.1802 (5)0.0514 (13)
H51.1370 (10)0.3966 (5)0.6715 (5)0.0532 (12)
H90.4800 (9)0.1024 (5)0.4320 (5)0.0549 (12)
H60.9997 (11)0.4397 (5)0.8769 (5)0.0602 (14)
H80.3403 (10)0.1454 (6)0.6355 (6)0.0570 (13)
H140.2271 (10)0.0345 (5)0.0377 (5)0.0556 (13)
H120.4225 (10)0.4649 (4)0.2825 (5)0.0560 (14)
HA1.1791 (10)0.2951 (5)0.3698 (6)0.0572 (13)
H11.0485 (11)−0.1217 (5)0.2613 (7)0.0671 (17)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0287 (11)0.0237 (8)0.0470 (13)0.0100 (8)0.0121 (9)0.0148 (8)
C20.0192 (9)0.0190 (7)0.0289 (9)0.0048 (6)0.0085 (7)0.0108 (7)
C30.0153 (8)0.0174 (6)0.0221 (8)0.0006 (6)0.0049 (6)0.0090 (6)
O10.0202 (11)0.0236 (9)0.0343 (13)−0.0032 (8)0.0080 (10)0.0136 (9)
C40.0151 (8)0.0152 (6)0.0199 (8)0.0012 (6)0.0034 (6)0.0083 (6)
C50.0220 (10)0.0198 (7)0.0235 (9)−0.0017 (6)0.0035 (7)0.0081 (7)
C60.0285 (10)0.0229 (8)0.0229 (9)0.0023 (7)0.0036 (8)0.0076 (7)
C70.0234 (10)0.0264 (8)0.0242 (9)0.0113 (7)0.0077 (7)0.0129 (7)
Cl10.0406 (10)0.0509 (9)0.0404 (9)0.0138 (7)0.0027 (7)0.0282 (7)
C80.0196 (10)0.0382 (9)0.0264 (10)0.0037 (8)0.0073 (8)0.0164 (8)
C90.0151 (9)0.0315 (9)0.0232 (9)−0.0041 (7)0.0031 (7)0.0123 (7)
C100.0215 (9)0.0156 (6)0.0209 (8)0.0024 (6)0.0062 (7)0.0090 (6)
C110.0281 (10)0.0165 (7)0.0283 (9)0.0010 (7)0.0030 (8)0.0118 (7)
C120.0324 (11)0.0241 (8)0.0333 (10)0.0069 (7)0.0071 (8)0.0183 (8)
C130.0287 (10)0.0302 (8)0.0245 (9)0.0065 (7)0.0057 (8)0.0164 (7)
Cl20.0442 (10)0.0591 (10)0.0338 (8)0.0204 (8)0.0194 (7)0.0230 (7)
C140.0303 (11)0.0274 (9)0.0260 (10)0.0048 (8)0.0012 (8)0.0101 (8)
C150.0301 (11)0.0187 (7)0.0241 (9)0.0044 (7)0.0022 (8)0.0067 (6)
H110.051 (3)0.0268 (17)0.053 (3)−0.0004 (17)−0.002 (2)0.0147 (18)
H150.057 (3)0.0279 (18)0.053 (3)0.0089 (18)−0.002 (2)0.0118 (17)
H50.042 (3)0.052 (2)0.045 (3)−0.018 (2)0.003 (2)0.016 (2)
H90.035 (3)0.071 (3)0.036 (2)−0.022 (2)−0.001 (2)0.019 (2)
H60.063 (4)0.054 (3)0.034 (2)−0.008 (2)0.001 (2)0.005 (2)
H80.035 (3)0.079 (3)0.059 (3)−0.003 (2)0.015 (2)0.038 (3)
H140.053 (3)0.044 (2)0.044 (3)0.002 (2)−0.007 (2)0.008 (2)
H120.063 (3)0.037 (2)0.070 (3)0.015 (2)0.005 (3)0.031 (2)
HA0.052 (3)0.057 (3)0.059 (3)−0.005 (2)0.032 (3)0.023 (2)
H10.070 (4)0.039 (2)0.093 (4)0.029 (2)0.029 (3)0.026 (3)
Geometric parameters (Å, º) top
C1—C21.200 (2)Cl1—C131.730 (2)
C1—H11.044 (4)C8—C91.389 (3)
C2—C31.467 (2)C8—H81.084 (6)
C3—O11.420 (3)C9—H91.075 (5)
C3—C101.528 (2)C10—C151.388 (2)
C3—C41.529 (3)C10—C111.388 (2)
O1—HA0.951 (7)C11—C121.385 (3)
C4—C51.385 (2)C11—H111.080 (5)
C4—C91.390 (3)C12—C131.389 (3)
C5—C61.393 (3)C12—H121.080 (4)
C5—H51.074 (6)C13—C141.382 (2)
C6—C71.386 (3)Cl2—Cl1i3.394 (2)
C6—H61.072 (5)C14—C151.387 (3)
C7—C81.378 (3)C14—H141.077 (5)
C7—Cl21.729 (3)C15—H151.086 (4)
C2—C1—H1179.4 (5)C9—C8—H8120.3 (4)
C1—C2—C3179.3 (2)C8—C9—C4120.58 (17)
O1—C3—C2109.59 (16)C8—C9—H9118.8 (3)
O1—C3—C10110.84 (15)C4—C9—H9120.6 (3)
C2—C3—C10111.64 (14)C15—C10—C11119.24 (15)
O1—C3—C4107.04 (16)C15—C10—C3122.25 (13)
C2—C3—C4108.89 (13)C11—C10—C3118.41 (14)
C10—C3—C4108.70 (14)C12—C11—C10120.99 (16)
C3—O1—HA109.4 (4)C12—C11—H11119.1 (3)
C5—C4—C9119.38 (17)C10—C11—H11119.9 (3)
C5—C4—C3121.94 (16)C11—C12—C13118.87 (15)
C9—C4—C3118.69 (15)C11—C12—H12121.6 (3)
C4—C5—C6120.45 (18)C13—C12—H12119.6 (3)
C4—C5—H5119.3 (3)C14—C13—C12120.92 (16)
C6—C5—H5120.2 (3)C14—C13—Cl1119.74 (15)
C7—C6—C5119.22 (17)C12—C13—Cl1119.29 (13)
C7—C6—H6120.9 (4)C7—Cl2—Cl1i93.85 (9)
C5—C6—H6119.9 (4)C13—C14—C15119.54 (17)
C8—C7—C6120.99 (19)C13—C14—H14119.7 (3)
C8—C7—Cl2119.03 (17)C15—C14—H14120.8 (3)
C6—C7—Cl2119.98 (15)C14—C15—C10120.42 (14)
C7—C8—C9119.38 (19)C14—C15—H15119.6 (3)
C7—C8—H8120.3 (4)C10—C15—H15119.9 (3)
Symmetry code: (i) x+1, y, z+1.
(4) top
Crystal data top
C15H10Br2OF(000) = 356
Mr = 366.05Dx = 1.801 Mg m−3
Triclinic, P1Melting point: 97 K
a = 5.7906 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.325 (2) ÅCell parameters from 998 reflections
c = 11.907 (2) Åθ = 4.3–30.5°
α = 115.67 (3)°µ = 5.99 mm−1
β = 99.43 (3)°T = 150 K
γ = 97.91 (3)°Block, colourless
V = 674.8 (2) Å30.4 × 0.3 × 0.2 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer		3456 independent reflections
Radiation source: fine-focus sealed tube2879 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
Detector resolution: not relevant pixels mm-1θmax = 30.2°, θmin = 2.0°
ω scansh = −6→8
Absorption correction: empirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)		k = −15→12
Tmin = 0.344, Tmax = 0.766l = −15→16
5364 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.072All H-atom parameters refined
S = 1.07 w = 1/[σ2(Fo2) + (0.0393P)2 + 0.1818P]
where P = (Fo2 + 2Fc2)/3
3456 reflections(Δ/σ)max = 0.001
203 parametersΔρmax = 0.86 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C15H10Br2Oγ = 97.91 (3)°
Mr = 366.05V = 674.8 (2) Å3
Triclinic, P1Z = 2
a = 5.7906 (12) ÅMo Kα radiation
b = 11.325 (2) ŵ = 5.99 mm−1
c = 11.907 (2) ÅT = 150 K
α = 115.67 (3)°0.4 × 0.3 × 0.2 mm
β = 99.43 (3)°
Data collection top
Bruker SMART CCD
diffractometer		3456 independent reflections
Absorption correction: empirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)		2879 reflections with I > 2σ(I)
Tmin = 0.344, Tmax = 0.766Rint = 0.029
5364 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.072All H-atom parameters refined
S = 1.07Δρmax = 0.86 e Å−3
3456 reflectionsΔρmin = −0.43 e Å−3
203 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br11.45503 (4)0.23580 (3)1.44526 (2)0.03392 (8)
Br20.95564 (5)0.17469 (3)0.60197 (2)0.03739 (8)
O10.3788 (3)0.17949 (17)1.05754 (17)0.0280 (3)
C100.6726 (4)0.2554 (2)0.9690 (2)0.0208 (4)
C150.8996 (4)0.3258 (2)0.9790 (2)0.0250 (4)
C140.9833 (4)0.3029 (2)0.8698 (2)0.0263 (4)
C30.5921 (4)0.2826 (2)1.0935 (2)0.0222 (4)
C20.5352 (4)0.4170 (2)1.1473 (2)0.0243 (4)
C120.6082 (4)0.1394 (2)0.7376 (2)0.0260 (4)
C110.5266 (4)0.1636 (2)0.8476 (2)0.0242 (4)
C50.9410 (4)0.3879 (2)1.2966 (2)0.0283 (5)
C10.4884 (4)0.5239 (3)1.1907 (3)0.0314 (5)
C40.7950 (4)0.2749 (2)1.1894 (2)0.0220 (4)
C130.8365 (4)0.2090 (2)0.7505 (2)0.0247 (4)
C71.1801 (4)0.2507 (2)1.3444 (2)0.0261 (4)
C81.0325 (4)0.1356 (2)1.2387 (2)0.0274 (4)
C61.1362 (4)0.3768 (2)1.3750 (2)0.0297 (5)
C90.8406 (4)0.1481 (2)1.1613 (2)0.0263 (4)
H50.909 (5)0.474 (3)1.312 (3)0.028 (7)*
H81.066 (5)0.052 (3)1.219 (3)0.038 (8)*
H150.994 (5)0.384 (3)1.057 (3)0.028 (7)*
H61.216 (6)0.454 (3)1.441 (3)0.054 (10)*
H141.135 (6)0.350 (3)0.878 (3)0.039 (8)*
H110.387 (6)0.115 (3)0.834 (3)0.036 (8)*
H90.758 (5)0.075 (3)1.094 (3)0.037 (8)*
H120.513 (5)0.076 (3)0.654 (3)0.034 (7)*
H1A0.327 (6)0.199 (3)1.117 (3)0.047 (10)*
H10.434 (7)0.600 (4)1.213 (4)0.064 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.03509 (14)0.03848 (14)0.02954 (13)0.01039 (10)0.00334 (9)0.01819 (11)
Br20.03590 (14)0.05276 (17)0.02461 (12)0.01797 (11)0.01266 (9)0.01505 (11)
O10.0243 (8)0.0249 (8)0.0304 (9)−0.0017 (6)0.0089 (7)0.0105 (7)
C100.0208 (9)0.0189 (9)0.0228 (10)0.0041 (7)0.0050 (8)0.0102 (8)
C150.0214 (10)0.0274 (11)0.0221 (10)0.0008 (8)0.0027 (8)0.0102 (9)
C140.0200 (10)0.0329 (11)0.0252 (11)0.0049 (8)0.0061 (8)0.0130 (9)
C30.0206 (9)0.0191 (9)0.0243 (10)0.0009 (7)0.0064 (8)0.0089 (8)
C20.0199 (9)0.0262 (10)0.0247 (10)0.0035 (8)0.0056 (8)0.0106 (9)
C120.0281 (11)0.0220 (10)0.0204 (10)0.0052 (8)−0.0006 (8)0.0057 (9)
C110.0212 (10)0.0191 (10)0.0283 (11)0.0006 (8)0.0033 (8)0.0097 (9)
C50.0337 (12)0.0226 (11)0.0245 (11)0.0070 (9)0.0046 (9)0.0080 (9)
C10.0262 (11)0.0278 (12)0.0372 (13)0.0077 (9)0.0076 (9)0.0122 (10)
C40.0255 (10)0.0205 (10)0.0220 (10)0.0044 (8)0.0089 (8)0.0109 (8)
C130.0281 (11)0.0277 (11)0.0235 (10)0.0138 (9)0.0094 (8)0.0134 (9)
C70.0272 (10)0.0315 (12)0.0230 (10)0.0075 (9)0.0070 (8)0.0153 (9)
C80.0301 (11)0.0231 (11)0.0311 (11)0.0057 (8)0.0075 (9)0.0147 (9)
C60.0340 (12)0.0248 (11)0.0216 (11)0.0040 (9)0.0015 (9)0.0058 (9)
C90.0290 (11)0.0208 (10)0.0254 (11)0.0016 (8)0.0050 (8)0.0094 (9)
Geometric parameters (Å, º) top
Br1—C71.904 (2)C12—C111.393 (3)
Br2—C131.906 (2)C12—H120.95 (3)
O1—C31.438 (3)C11—H110.86 (3)
O1—H1A0.76 (3)C5—C41.384 (3)
C10—C111.393 (3)C5—C61.400 (3)
C10—C151.398 (3)C5—H50.97 (3)
C10—C31.543 (3)C1—H10.90 (4)
C15—C141.394 (3)C4—C91.401 (3)
C15—H150.90 (3)C7—C61.385 (3)
C14—C131.385 (3)C7—C81.390 (3)
C14—H140.93 (3)C8—C91.387 (3)
C3—C21.483 (3)C8—H80.93 (3)
C3—C41.538 (3)C6—H60.88 (4)
C2—C11.184 (3)C9—H90.86 (3)
C12—C131.391 (3)
C3—O1—H1A107 (3)C4—C5—C6120.7 (2)
C11—C10—C15119.2 (2)C4—C5—H5117.6 (17)
C11—C10—C3122.18 (19)C6—C5—H5121.6 (17)
C15—C10—C3118.60 (19)C2—C1—H1172 (3)
C14—C15—C10121.0 (2)C5—C4—C9119.3 (2)
C14—C15—H15119.6 (18)C5—C4—C3122.84 (19)
C10—C15—H15119.4 (18)C9—C4—C3117.7 (2)
C13—C14—C15118.6 (2)C14—C13—C12121.6 (2)
C13—C14—H14121 (2)C14—C13—Br2118.38 (17)
C15—C14—H14120 (2)C12—C13—Br2120.01 (17)
O1—C3—C2109.93 (18)C6—C7—C8121.2 (2)
O1—C3—C4110.93 (17)C6—C7—Br1119.26 (18)
C2—C3—C4111.32 (18)C8—C7—Br1119.49 (17)
O1—C3—C10106.56 (17)C9—C8—C7119.2 (2)
C2—C3—C10109.10 (17)C9—C8—H8120.7 (19)
C4—C3—C10108.86 (17)C7—C8—H8120.1 (19)
C1—C2—C3179.4 (2)C7—C6—C5119.0 (2)
C13—C12—C11119.1 (2)C7—C6—H6127 (2)
C13—C12—H12118.7 (17)C5—C6—H6114 (2)
C11—C12—H12122.1 (17)C8—C9—C4120.5 (2)
C12—C11—C10120.4 (2)C8—C9—H9117 (2)
C12—C11—H11115 (2)C4—C9—H9123 (2)
C10—C11—H11125 (2)
(5) top
Crystal data top
C27H20OF(000) = 380
Mr = 360.43Dx = 1.235 Mg m−3
Triclinic, P1Melting point: 157 K
a = 5.6413 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2599 (5) ÅCell parameters from 927 reflections
c = 17.3238 (9) Åθ = 10.2–26.5°
α = 100.450 (2)°µ = 0.07 mm−1
β = 97.790 (2)°T = 150 K
γ = 95.477 (2)°Plate, colourless
V = 969.51 (9) Å30.4 × 0.25 × 0.1 mm
Z = 2
Data collection top
Bruker SMART CCD
diffractometer		5270 independent reflections
Radiation source: fine-focus sealed tube3419 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: not relevant pixels mm-1θmax = 30.5°, θmin = 1.2°
ω scansh = −7→7
Absorption correction: empirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)		k = −14→13
Tmin = 0.681, Tmax = 0.884l = −21→23
12424 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: difference Fourier map
wR(F2) = 0.234All H-atom parameters refined
S = 1.04 w = 1/[σ2(Fo2) + (0.1193P)2 + 0.578P]
where P = (Fo2 + 2Fc2)/3
5270 reflections(Δ/σ)max < 0.001
322 parametersΔρmax = 0.50 e Å−3
0 restraintsΔρmin = −0.43 e Å−3
Crystal data top
C27H20Oγ = 95.477 (2)°
Mr = 360.43V = 969.51 (9) Å3
Triclinic, P1Z = 2
a = 5.6413 (3) ÅMo Kα radiation
b = 10.2599 (5) ŵ = 0.07 mm−1
c = 17.3238 (9) ÅT = 150 K
α = 100.450 (2)°0.4 × 0.25 × 0.1 mm
β = 97.790 (2)°
Data collection top
Bruker SMART CCD
diffractometer		5270 independent reflections
Absorption correction: empirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)		3419 reflections with I > 2σ(I)
Tmin = 0.681, Tmax = 0.884Rint = 0.043
12424 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0760 restraints
wR(F2) = 0.234All H-atom parameters refined
S = 1.04Δρmax = 0.50 e Å−3
5270 reflectionsΔρmin = −0.43 e Å−3
322 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0423 (4)−0.0743 (3)0.29797 (15)0.0354 (5)
H1−0.037 (6)−0.155 (3)0.2918 (18)0.049 (8)*
C20.1443 (4)0.0348 (2)0.30668 (13)0.0297 (5)
C30.2633 (4)0.1735 (2)0.31647 (13)0.0277 (4)
O10.0883 (3)0.26591 (16)0.32794 (10)0.0326 (4)
H1A−0.003 (8)0.238 (4)0.360 (3)0.096 (14)*
C40.3638 (4)0.1901 (2)0.24024 (13)0.0275 (4)
C50.2812 (6)0.2778 (3)0.19456 (17)0.0510 (8)
H50.149 (7)0.331 (4)0.211 (2)0.085 (12)*
C60.3804 (7)0.2913 (4)0.12649 (19)0.0662 (10)
H60.294 (8)0.355 (4)0.093 (3)0.098 (14)*
C70.5632 (4)0.2191 (2)0.10295 (15)0.0387 (5)*
C80.6933 (12)0.2569 (7)0.0337 (4)0.0444 (16)*0.50
C90.7488 (13)0.1532 (8)−0.0184 (4)0.0479 (17)*0.50
C110.8695 (17)0.1854 (10)−0.0857 (6)0.070 (2)*0.50
C100.9392 (17)0.3032 (10)−0.0909 (6)0.079 (2)*0.50
C120.9046 (16)0.4169 (8)−0.0341 (5)0.076 (2)*0.50
C130.7765 (13)0.3910 (7)0.0277 (4)0.0614 (16)*0.50
C8A0.6508 (10)0.2181 (6)0.0279 (3)0.0345 (13)*0.50
C9A0.8893 (16)0.1860 (9)0.0183 (5)0.0309 (18)*0.25
C10A0.984 (2)0.1971 (11)−0.0516 (7)0.045 (2)*0.25
C11A0.776 (3)0.2539 (14)−0.1172 (8)0.051 (4)*0.25
C12A0.595 (2)0.2654 (12)−0.1054 (7)0.051 (3)*0.25
C13A0.5090 (19)0.2510 (11)−0.0363 (7)0.042 (2)*0.25
C9B0.755 (2)0.1131 (15)−0.0142 (9)0.047 (3)*0.25
C10B0.8428 (18)0.1373 (12)−0.0838 (6)0.032 (2)*0.25
C11B0.857 (2)0.2489 (10)−0.1105 (6)0.0241 (19)*0.25
C12B0.758 (2)0.3675 (13)−0.0672 (8)0.054 (3)*0.25
C13B0.654 (2)0.3512 (11)−0.0001 (7)0.044 (2)*0.25
C140.6400 (5)0.1299 (3)0.14867 (16)0.0410 (6)
H140.770 (6)0.076 (3)0.134 (2)0.064 (10)*
C150.5424 (5)0.1155 (3)0.21671 (17)0.0418 (6)
H150.594 (5)0.052 (3)0.2491 (19)0.051 (8)*
C160.4697 (4)0.2080 (2)0.38763 (13)0.0265 (4)
C170.5842 (4)0.1103 (2)0.41913 (14)0.0302 (5)
H170.528 (5)0.014 (3)0.3960 (16)0.034 (7)*
C180.7747 (4)0.1467 (2)0.48245 (14)0.0291 (5)
H180.844 (5)0.079 (3)0.5071 (16)0.033 (6)*
C190.8535 (3)0.2812 (2)0.51612 (12)0.0248 (4)
C201.0514 (3)0.3190 (2)0.58493 (12)0.0247 (4)
C211.2571 (4)0.2522 (2)0.58795 (14)0.0287 (5)
H211.280 (4)0.184 (3)0.5441 (16)0.030 (6)*
C221.4380 (4)0.2851 (2)0.65346 (15)0.0342 (5)
H221.568 (5)0.238 (3)0.6546 (18)0.047 (8)*
C231.4181 (5)0.3860 (3)0.71682 (16)0.0414 (6)
H231.546 (6)0.409 (3)0.761 (2)0.063 (10)*
C241.2180 (4)0.4552 (3)0.71411 (15)0.0385 (6)
H241.204 (5)0.529 (3)0.7583 (19)0.049 (8)*
C251.0358 (4)0.4217 (2)0.64876 (14)0.0299 (5)
H250.895 (5)0.470 (2)0.6447 (15)0.032 (6)*
C260.7358 (4)0.3784 (2)0.48418 (13)0.0262 (4)
H260.789 (5)0.472 (3)0.5058 (16)0.032 (6)*
C270.5500 (4)0.3425 (2)0.42013 (13)0.0272 (4)
H270.480 (4)0.413 (2)0.3993 (15)0.029 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0339 (12)0.0358 (13)0.0369 (13)0.0007 (9)0.0085 (9)0.0081 (10)
C20.0264 (10)0.0353 (12)0.0279 (11)0.0050 (8)0.0066 (8)0.0052 (9)
C30.0245 (9)0.0285 (10)0.0301 (11)0.0059 (7)0.0052 (8)0.0041 (8)
O10.0271 (8)0.0353 (9)0.0371 (9)0.0112 (6)0.0084 (7)0.0056 (7)
C40.0241 (9)0.0288 (10)0.0266 (10)0.0010 (7)0.0016 (8)0.0008 (8)
C50.0592 (17)0.0696 (19)0.0394 (15)0.0392 (15)0.0208 (13)0.0244 (14)
C60.079 (2)0.096 (3)0.0475 (18)0.055 (2)0.0288 (16)0.0400 (18)
C140.0375 (12)0.0429 (14)0.0463 (15)0.0099 (10)0.0192 (11)0.0066 (11)
C150.0414 (13)0.0413 (14)0.0526 (16)0.0166 (11)0.0213 (12)0.0185 (12)
C160.0245 (9)0.0287 (10)0.0268 (10)0.0046 (7)0.0068 (8)0.0038 (8)
C170.0309 (10)0.0238 (10)0.0356 (12)0.0064 (8)0.0055 (9)0.0028 (8)
C180.0302 (10)0.0250 (10)0.0332 (11)0.0089 (8)0.0047 (8)0.0058 (8)
C190.0238 (9)0.0265 (10)0.0257 (10)0.0035 (7)0.0080 (7)0.0060 (8)
C200.0231 (9)0.0269 (10)0.0264 (10)0.0030 (7)0.0073 (7)0.0092 (8)
C210.0271 (10)0.0305 (11)0.0308 (11)0.0057 (8)0.0094 (8)0.0073 (9)
C220.0265 (10)0.0387 (12)0.0403 (13)0.0080 (9)0.0061 (9)0.0124 (10)
C230.0334 (12)0.0521 (15)0.0345 (13)0.0078 (10)−0.0038 (10)0.0030 (11)
C240.0372 (12)0.0439 (14)0.0309 (12)0.0080 (10)0.0029 (9)−0.0010 (10)
C250.0271 (10)0.0324 (11)0.0317 (11)0.0062 (8)0.0075 (8)0.0066 (9)
C260.0279 (10)0.0226 (10)0.0293 (11)0.0035 (7)0.0079 (8)0.0051 (8)
C270.0288 (10)0.0263 (10)0.0286 (11)0.0061 (8)0.0066 (8)0.0076 (8)
Geometric parameters (Å, º) top
C1—C21.182 (3)C9A—C10A1.406 (15)
C1—H10.89 (3)C10A—C11A1.74 (2)
C2—C31.485 (3)C11A—C12A1.078 (18)
C3—O11.441 (2)C12A—C13A1.380 (16)
C3—C41.536 (3)C9B—C10B1.418 (18)
C3—C161.541 (3)C10B—C11B1.309 (15)
O1—H1A0.87 (5)C11B—C12B1.507 (16)
C4—C51.375 (3)C12B—C13B1.399 (17)
C4—C151.383 (3)C14—C151.392 (4)
C5—C61.395 (4)C14—H140.99 (3)
C5—H51.01 (4)C15—H150.97 (3)
C6—C71.388 (4)C16—C171.396 (3)
C6—H61.06 (4)C16—C271.398 (3)
C7—C141.378 (4)C17—C181.397 (3)
C7—C8A1.451 (6)C17—H171.00 (3)
C7—C81.576 (7)C18—C191.401 (3)
C8—C13B1.240 (13)C18—H180.96 (3)
C8—C91.356 (10)C19—C261.403 (3)
C8—C9A1.409 (11)C19—C201.485 (3)
C8—C131.436 (10)C20—C251.401 (3)
C8—C13A1.474 (12)C20—C211.403 (3)
C8—C9B1.649 (16)C21—C221.387 (3)
C9—C8A1.179 (9)C21—H210.97 (3)
C9—C111.498 (12)C22—C231.390 (4)
C11—C101.257 (14)C22—H220.92 (3)
C10—C121.431 (12)C23—C241.390 (3)
C12—C131.419 (11)C23—H230.96 (3)
C12—C12i2.009 (18)C24—C251.390 (3)
C13—C8A1.847 (10)C24—H240.99 (3)
C8A—C13A1.391 (12)C25—H250.98 (3)
C8A—C9B1.410 (16)C26—C271.389 (3)
C8A—C9A1.439 (10)C26—H260.97 (3)
C8A—C13B1.529 (13)C27—H270.96 (2)
C2—C1—H1179 (2)C9A—C8A—C13B100.9 (7)
C1—C2—C3177.7 (2)C7—C8A—C13B114.5 (6)
O1—C3—C2109.60 (17)C9—C8A—C13103.2 (6)
O1—C3—C4107.55 (17)C13A—C8A—C1376.2 (6)
C2—C3—C4109.28 (18)C9B—C8A—C13117.8 (7)
O1—C3—C16109.25 (16)C9A—C8A—C1384.9 (5)
C2—C3—C16111.68 (18)C7—C8A—C13107.3 (4)
C4—C3—C16109.38 (16)C13B—C8A—C1325.7 (4)
C3—O1—H1A107 (3)C10A—C9A—C8117.0 (8)
C5—C4—C15118.8 (2)C10A—C9A—C8A121.1 (8)
C5—C4—C3121.7 (2)C8—C9A—C8A17.4 (3)
C15—C4—C3119.5 (2)C9A—C10A—C11A110.2 (9)
C4—C5—C6119.8 (2)C12A—C11A—C10A121.6 (13)
C4—C5—H5119 (2)C11A—C12A—C13A125.9 (14)
C6—C5—H5121 (2)C12A—C13A—C8A122.6 (9)
C7—C6—C5122.1 (3)C12A—C13A—C8115.8 (9)
C7—C6—H6124 (2)C8A—C13A—C817.1 (4)
C5—C6—H6114 (2)C8A—C9B—C10B116.2 (12)
C14—C7—C6117.2 (2)C8A—C9B—C813.6 (4)
C14—C7—C8A118.5 (3)C10B—C9B—C8107.3 (11)
C6—C7—C8A123.7 (3)C11B—C10B—C9B128.0 (11)
C14—C7—C8123.6 (3)C10B—C11B—C12B119.0 (9)
C6—C7—C8118.6 (3)C13B—C12B—C11B117.3 (11)
C8A—C7—C815.8 (3)C8—C13B—C12B121.1 (10)
C13B—C8—C9110.1 (8)C8—C13B—C8A13.4 (4)
C13B—C8—C9A119.4 (8)C12B—C13B—C8A120.1 (9)
C9—C8—C9A39.6 (5)C7—C14—C15121.3 (2)
C13B—C8—C1334.3 (6)C7—C14—H14120 (2)
C9—C8—C13119.2 (7)C15—C14—H14119 (2)
C9A—C8—C13103.8 (6)C4—C15—C14120.8 (2)
C13B—C8—C13A54.5 (7)C4—C15—H15117.1 (19)
C9—C8—C13A78.1 (6)C14—C15—H15122.1 (19)
C9A—C8—C13A114.7 (7)C17—C16—C27118.86 (19)
C13—C8—C13A88.5 (6)C17—C16—C3122.48 (19)
C13B—C8—C7125.4 (7)C27—C16—C3118.63 (18)
C9—C8—C7116.0 (6)C16—C17—C18120.3 (2)
C9A—C8—C7114.6 (6)C16—C17—H17119.2 (15)
C13—C8—C7124.5 (6)C18—C17—H17120.4 (15)
C13A—C8—C7108.4 (6)C17—C18—C19121.09 (19)
C13B—C8—C9B122.2 (9)C17—C18—H18120.2 (15)
C9—C8—C9B12.3 (6)C19—C18—H18118.5 (15)
C9A—C8—C9B38.7 (6)C18—C19—C26117.96 (19)
C13—C8—C9B130.0 (7)C18—C19—C20120.75 (18)
C13A—C8—C9B85.3 (7)C26—C19—C20121.27 (18)
C7—C8—C9B104.4 (7)C25—C20—C21118.40 (19)
C8A—C9—C818.0 (4)C25—C20—C19120.66 (18)
C8A—C9—C11132.2 (8)C21—C20—C19120.94 (19)
C8—C9—C11117.4 (7)C22—C21—C20120.7 (2)
C10—C11—C9122.5 (8)C22—C21—H21117.7 (15)
C11—C10—C12122.7 (9)C20—C21—H21121.6 (15)
C13—C12—C10116.5 (8)C21—C22—C23120.2 (2)
C13—C12—C12i92.8 (7)C21—C22—H22118.8 (19)
C10—C12—C12i139.5 (9)C23—C22—H22121.0 (19)
C12—C13—C8121.3 (7)C22—C23—C24119.9 (2)
C12—C13—C8A119.6 (6)C22—C23—H23119 (2)
C8—C13—C8A4.8 (4)C24—C23—H23121 (2)
C9—C8A—C13A87.6 (7)C25—C24—C23120.0 (2)
C9—C8A—C9B16.4 (7)C25—C24—H24119.4 (17)
C13A—C8A—C9B98.4 (8)C23—C24—H24120.7 (17)
C9—C8A—C9A40.5 (5)C24—C25—C20120.8 (2)
C13A—C8A—C9A118.1 (7)C24—C25—H25121.6 (15)
C9B—C8A—C9A42.7 (7)C20—C25—H25117.5 (15)
C9—C8A—C7142.1 (6)C27—C26—C19121.04 (19)
C13A—C8A—C7121.0 (6)C27—C26—H26119.4 (15)
C9B—C8A—C7125.9 (7)C19—C26—H26119.5 (15)
C9A—C8A—C7120.9 (5)C26—C27—C16120.68 (19)
C9—C8A—C13B102.8 (7)C26—C27—H27117.4 (15)
C13A—C8A—C13B50.9 (6)C16—C27—H27121.9 (15)
C9B—C8A—C13B119.2 (9)
Symmetry code: (i) −x+2, −y+1, −z.

Experimental details

(2)(3X)(3N)(4)
Crystal data
Chemical formulaC17H16OC15H10Cl2OC15H10Cl2OC15H10Br2O
Mr236.30277.13277.13366.05
Crystal system, space groupTriclinic, P1Triclinic, P1Triclinic, P1Triclinic, P1
Temperature (K)150150150150
a, b, c (Å)6.8286 (14), 8.2407 (16), 12.658 (3)5.7082 (1), 11.3645 (2), 11.5167 (1)5.7280 (1), 11.3620 (2), 11.5210 (1)5.7906 (12), 11.325 (2), 11.907 (2)
α, β, γ (°)106.73 (3), 98.71 (3), 101.39 (3)117.268 (1), 99.257 (1), 96.726 (1)117.240 (1), 99.250 (1), 96.860 (1)115.67 (3), 99.43 (3), 97.91 (3)
V (Å3)652.0 (2)639.73 (2)641.87 (2)674.8 (2)
Z2222
Radiation typeMo KαMo KαNeutron, λ = 0.5-5.0 ÅMo Kα
µ (mm−1)0.070.491.45 at 1 angstrom5.99
Crystal size (mm)0.3 × 0.3 × 0.20.5 × 0.4 × 0.42.5 × 1.5 × 1.00.4 × 0.3 × 0.2
Data collection
DiffractometerBruker SMART CCDBruker SMART CCDSXDBruker SMART CCD
Absorption correctionMulti-scan
SADABS (Sheldrick 1996)		Multi-scan
SADABS (Sheldrick 1996)		Empirical (using intensity measurements)
The linear absorption coefficient is wavelength dependent and it is calculated as: mu = 0.64 + 0.81 * lambda [cm-1]		Empirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)
Tmin, Tmax0.784, 1.0000.284, 0.3320.51, 0.890.344, 0.766
No. of measured, independent and
observed [I > 2σ(I)] reflections		4775, 2964, 2362 4371, 2826, 2617 10674, 2929, 2928 5364, 3456, 2879
Rint0.0180.0430.0620.029
(sin θ/λ)max (Å−1)0.6490.646–0.707
Distance from specimen to detector (mm)––h = 0→12, k = −20→21, l = −19→10–
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.132, 1.03 0.038, 0.104, 1.11 0.067, 0.128, 5.44 0.028, 0.072, 1.07
No. of reflections2964282629293456
No. of parameters231203253203
H-atom treatmentAll H-atom parameters refinedH atoms treated by a mixture of independent and constrained refinementAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.21, −0.200.33, −0.35?, ?0.86, −0.43


(5)
Crystal data
Chemical formulaC27H20O
Mr360.43
Crystal system, space groupTriclinic, P1
Temperature (K)150
a, b, c (Å)5.6413 (3), 10.2599 (5), 17.3238 (9)
α, β, γ (°)100.450 (2), 97.790 (2), 95.477 (2)
V (Å3)969.51 (9)
Z2
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.4 × 0.25 × 0.1
Data collection
DiffractometerBruker SMART CCD
Absorption correctionEmpirical (using intensity measurements)
(XPREP in SHELX97; Sheldrick, 1997)
Tmin, Tmax0.681, 0.884
No. of measured, independent and
observed [I > 2σ(I)] reflections		12424, 5270, 3419
Rint0.043
(sin θ/λ)max (Å−1)0.713
Distance from specimen to detector (mm)–
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.234, 1.04
No. of reflections5270
No. of parameters322
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.50, −0.43

Computer programs: Bruker SMART (Bruker Systems Inc., 1999a), SXD (Keen & Wilson, 1996), Bruker SAINT (Bruker Systems Inc., 1999b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) for (2) top
D—H···AD—HH···AD···AD—H···A
O1—HA···C11i0.85 (3)3.07 (3)3.860 (2)155 (2)
O1—HA···C13i0.85 (3)2.85 (3)3.644 (2)156 (2)
O1—HA···C16i0.85 (3)2.61 (3)3.288 (2)137 (2)
Symmetry code: (i) −x+1, −y, −z.
 

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