D. A. Zherebtsov,
M. U. Schmidt,
R. Niewa,
C. P. Sakthidharan,
F. V. Podgornov,
Y. V. Matveychuk,
S. A. Nayfert,
M. A. Polozov,
S. N. Ivashevskaya,
A. I. Stash,
Y.-S. Chen,
D. E. Zhivulin,
V. E. Zhivulin,
S. V. Merzlov,
E. V. Bartashevich,
V. V. Avdin,
H. S. Hsu and
F. W. Guo The crystal structures of two polymorphs of cis-perinone (bisbenzimidazo[2,1-b:1′,2′-j]benzo[lmn][3,8]phenanthroline-6,9-dione, Pigment Red 194) were solved from single crystals obtained solvothermally from 1,2-dichlorobenzene or n-butanol at 220°C. Both crystal structures (space group P21/c) derive from stacking of flat molecules arranged due to π–π interaction. The melting points of these two polymorphs are 471°C and 468°C and their respective optical bandgaps are 1.94 eV and 1.71 eV. One of the polymorphs demonstrates drift and hopping mechanisms of electric conductivity, whereas the other one is dominated by the drift conductivity. The direct current (DC) electric conductivity of the samples are 4.77 × 10−13 S m−1 and 6.84 × 10−10 S m−1 at room temperature. The significant difference in DC conductivities can be explained by the dependence of the mobility and concentration of charge carriers on the structure of the samples.
Supporting information
CCDC references: 1872270; 1872790; 1872791
Data collection: APEX II v.2013.6-2, (Bruker, 2013) for polymorph1. Cell refinement: SAINT V8.32B (Bruker AXS Inc., 2013) for polymorph1. Data reduction: SAINT V8.32B (Bruker AXS Inc., 2013) for polymorph1. Program(s) used to solve structure: SHELXT-2014/4 (Sheldrick, 2014) for polymorph1; SHELXS97 (Sheldrick, 1990) for polymorph2. Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014) for polymorph1; SHELXL97 (Sheldrick, 1997) for polymorph2. Molecular graphics: Bruker SHELXTL (Bruker AXS Inc., 2013) for polymorph1.
bisbenzimidazo[2,1-b:1',2'-j]benzo[lmn][3,8]phenanthroline-6,9-dione (polymorph1)
top
Crystal data top
C26H12N4O2 | Dx = 1.604 Mg m−3 |
Mr = 412.40 | Melting point: 744 K |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.41328 Å |
a = 13.1190 (8) Å | Cell parameters from 5223 reflections |
b = 4.7770 (3) Å | θ = 2.4–17.4° |
c = 27.3921 (17) Å | µ = 0.03 mm−1 |
β = 95.8533 (12)° | T = 100 K |
V = 1707.70 (18) Å3 | Plate, red |
Z = 4 | 0.05 × 0.02 × 0.01 mm |
F(000) = 848 | |
Data collection top
Bruker APEX II CCD diffractometer | 3679 reflections with I > 2σ(I) |
Radiation source: Advanced photon source | Rint = 0.075 |
Diamond (111) monochromator | θmax = 17.7°, θmin = 0.9° |
φ–scan | h = −19→19 |
26791 measured reflections | k = −6→4 |
5376 independent reflections | l = −39→40 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.203 | w = 1/[σ2(Fo2) + (0.1151P)2 + 0.2566P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
5376 reflections | Δρmax = 0.66 e Å−3 |
289 parameters | Δρmin = −0.32 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.54706 (10) | −0.1783 (3) | 0.45993 (5) | 0.0297 (3) | |
O2 | 0.56344 (10) | 0.8576 (3) | 0.27759 (5) | 0.0286 (3) | |
N1 | 0.70844 (11) | −0.0567 (3) | 0.49048 (5) | 0.0212 (3) | |
N2 | 0.86812 (11) | 0.0372 (3) | 0.52634 (5) | 0.0229 (3) | |
N3 | 0.72829 (11) | 0.9507 (3) | 0.30653 (5) | 0.0191 (3) | |
N4 | 0.89346 (11) | 1.0686 (3) | 0.32888 (5) | 0.0215 (3) | |
C1 | 0.62860 (13) | 0.1885 (3) | 0.41937 (6) | 0.0209 (3) | |
C2 | 0.71995 (13) | 0.3459 (3) | 0.41729 (6) | 0.0186 (3) | |
C3 | 0.80751 (13) | 0.2996 (3) | 0.45135 (6) | 0.0199 (3) | |
C4 | 0.89671 (14) | 0.4462 (4) | 0.44682 (6) | 0.0218 (3) | |
H4B | 0.9559 | 0.4093 | 0.4689 | 0.026* | |
C5 | 0.90112 (13) | 0.6486 (4) | 0.41013 (6) | 0.0218 (3) | |
H5A | 0.9628 | 0.7499 | 0.4079 | 0.026* | |
C6 | 0.81646 (13) | 0.7023 (3) | 0.37711 (6) | 0.0191 (3) | |
C7 | 0.72450 (13) | 0.5485 (3) | 0.38001 (6) | 0.0184 (3) | |
C8 | 0.63626 (13) | 0.5911 (4) | 0.34588 (6) | 0.0208 (3) | |
C9 | 0.54899 (13) | 0.4329 (4) | 0.34854 (7) | 0.0244 (4) | |
H9A | 0.4911 | 0.4610 | 0.3252 | 0.029* | |
C10 | 0.54526 (14) | 0.2317 (4) | 0.38528 (7) | 0.0242 (4) | |
H10A | 0.4849 | 0.1237 | 0.3868 | 0.029* | |
C11 | 0.62146 (13) | −0.0307 (4) | 0.45749 (6) | 0.0229 (4) | |
C12 | 0.72339 (14) | −0.2321 (4) | 0.53177 (6) | 0.0228 (4) | |
C13 | 0.66126 (15) | −0.4327 (4) | 0.55088 (7) | 0.0266 (4) | |
H13A | 0.5945 | −0.4743 | 0.5359 | 0.032* | |
C14 | 0.70286 (16) | −0.5680 (4) | 0.59313 (7) | 0.0288 (4) | |
H14A | 0.6638 | −0.7079 | 0.6074 | 0.035* | |
C15 | 0.80114 (16) | −0.5032 (4) | 0.61524 (7) | 0.0298 (4) | |
H15A | 0.8266 | −0.5993 | 0.6443 | 0.036* | |
C16 | 0.86218 (16) | −0.3031 (4) | 0.59594 (7) | 0.0269 (4) | |
H16A | 0.9286 | −0.2599 | 0.6112 | 0.032* | |
C17 | 0.82195 (14) | −0.1685 (4) | 0.55339 (6) | 0.0239 (4) | |
C18 | 0.79938 (13) | 0.0971 (4) | 0.49012 (6) | 0.0202 (3) | |
C19 | 0.63632 (13) | 0.8050 (3) | 0.30698 (6) | 0.0218 (3) | |
C20 | 0.75207 (13) | 1.1609 (3) | 0.27367 (6) | 0.0199 (3) | |
C21 | 0.69356 (14) | 1.2934 (4) | 0.23530 (6) | 0.0243 (4) | |
H21A | 0.6235 | 1.2484 | 0.2267 | 0.029* | |
C22 | 0.74393 (14) | 1.4964 (4) | 0.21025 (7) | 0.0247 (4) | |
H22A | 0.7077 | 1.5918 | 0.1834 | 0.030* | |
C23 | 0.84649 (14) | 1.5623 (4) | 0.22376 (6) | 0.0247 (4) | |
H23A | 0.8787 | 1.6999 | 0.2055 | 0.030* | |
C24 | 0.90276 (14) | 1.4335 (4) | 0.26291 (7) | 0.0247 (4) | |
H24A | 0.9721 | 1.4834 | 0.2722 | 0.030* | |
C25 | 0.85440 (13) | 1.2285 (4) | 0.28826 (6) | 0.0207 (3) | |
C26 | 0.81756 (12) | 0.9084 (3) | 0.33848 (6) | 0.0191 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0280 (7) | 0.0265 (7) | 0.0351 (8) | −0.0075 (5) | 0.0059 (6) | 0.0011 (5) |
O2 | 0.0232 (6) | 0.0261 (7) | 0.0345 (7) | −0.0015 (5) | −0.0070 (5) | 0.0039 (5) |
N1 | 0.0240 (7) | 0.0181 (7) | 0.0219 (7) | −0.0033 (5) | 0.0043 (5) | −0.0012 (5) |
N2 | 0.0287 (8) | 0.0203 (7) | 0.0197 (7) | −0.0003 (6) | 0.0022 (6) | 0.0000 (5) |
N3 | 0.0205 (7) | 0.0157 (7) | 0.0207 (7) | 0.0005 (5) | 0.0003 (5) | −0.0004 (5) |
N4 | 0.0233 (7) | 0.0189 (7) | 0.0224 (7) | −0.0009 (5) | 0.0027 (5) | −0.0003 (5) |
C1 | 0.0245 (8) | 0.0147 (8) | 0.0241 (8) | −0.0009 (6) | 0.0046 (6) | −0.0035 (6) |
C2 | 0.0234 (8) | 0.0138 (7) | 0.0188 (7) | 0.0008 (6) | 0.0026 (6) | −0.0023 (6) |
C3 | 0.0242 (8) | 0.0163 (8) | 0.0194 (7) | 0.0006 (6) | 0.0037 (6) | −0.0016 (6) |
C4 | 0.0254 (8) | 0.0201 (8) | 0.0194 (8) | −0.0002 (6) | 0.0000 (6) | −0.0007 (6) |
C5 | 0.0238 (8) | 0.0191 (8) | 0.0223 (8) | −0.0023 (6) | 0.0015 (6) | −0.0014 (6) |
C6 | 0.0228 (8) | 0.0150 (8) | 0.0197 (7) | 0.0012 (6) | 0.0030 (6) | −0.0029 (6) |
C7 | 0.0219 (8) | 0.0130 (7) | 0.0204 (7) | 0.0018 (6) | 0.0028 (6) | −0.0019 (5) |
C8 | 0.0245 (8) | 0.0152 (8) | 0.0225 (8) | 0.0017 (6) | 0.0019 (6) | −0.0018 (6) |
C9 | 0.0213 (8) | 0.0205 (9) | 0.0307 (9) | 0.0001 (6) | −0.0015 (7) | −0.0012 (7) |
C10 | 0.0230 (8) | 0.0196 (8) | 0.0301 (9) | −0.0006 (6) | 0.0026 (7) | −0.0022 (7) |
C11 | 0.0245 (8) | 0.0202 (8) | 0.0245 (8) | −0.0012 (6) | 0.0050 (7) | −0.0046 (6) |
C12 | 0.0319 (9) | 0.0170 (8) | 0.0204 (8) | 0.0023 (6) | 0.0073 (7) | −0.0012 (6) |
C13 | 0.0340 (10) | 0.0216 (9) | 0.0257 (9) | −0.0007 (7) | 0.0092 (7) | −0.0010 (7) |
C14 | 0.0411 (11) | 0.0213 (9) | 0.0256 (9) | −0.0013 (7) | 0.0122 (8) | 0.0009 (7) |
C15 | 0.0422 (11) | 0.0232 (9) | 0.0250 (9) | 0.0013 (8) | 0.0080 (8) | 0.0032 (7) |
C16 | 0.0362 (10) | 0.0227 (9) | 0.0224 (8) | 0.0013 (7) | 0.0059 (7) | 0.0010 (6) |
C17 | 0.0309 (9) | 0.0208 (8) | 0.0208 (8) | 0.0004 (7) | 0.0059 (7) | −0.0017 (6) |
C18 | 0.0240 (8) | 0.0173 (8) | 0.0193 (7) | −0.0007 (6) | 0.0024 (6) | −0.0026 (6) |
C19 | 0.0213 (8) | 0.0167 (8) | 0.0271 (9) | −0.0008 (6) | 0.0009 (6) | −0.0035 (6) |
C20 | 0.0246 (8) | 0.0161 (8) | 0.0191 (7) | 0.0012 (6) | 0.0024 (6) | −0.0020 (6) |
C21 | 0.0259 (8) | 0.0223 (9) | 0.0239 (8) | 0.0009 (6) | −0.0010 (6) | −0.0041 (6) |
C22 | 0.0314 (9) | 0.0195 (8) | 0.0230 (8) | 0.0007 (7) | 0.0018 (7) | −0.0011 (6) |
C23 | 0.0310 (9) | 0.0200 (9) | 0.0238 (8) | −0.0007 (7) | 0.0057 (7) | 0.0008 (6) |
C24 | 0.0265 (9) | 0.0208 (9) | 0.0272 (9) | −0.0009 (6) | 0.0047 (7) | 0.0003 (6) |
C25 | 0.0221 (8) | 0.0174 (8) | 0.0224 (8) | 0.0006 (6) | 0.0016 (6) | −0.0019 (6) |
C26 | 0.0204 (8) | 0.0160 (8) | 0.0206 (7) | 0.0011 (6) | 0.0006 (6) | −0.0023 (6) |
Geometric parameters (Å, º) top
O1—C11 | 1.211 (2) | C8—C9 | 1.380 (2) |
O2—C19 | 1.212 (2) | C8—C19 | 1.476 (2) |
N1—C11 | 1.387 (2) | C9—C10 | 1.396 (3) |
N1—C18 | 1.402 (2) | C9—H9A | 0.9500 |
N1—C12 | 1.405 (2) | C10—H10A | 0.9500 |
N2—C18 | 1.303 (2) | C12—C13 | 1.394 (2) |
N2—C17 | 1.404 (2) | C12—C17 | 1.400 (3) |
N3—C19 | 1.394 (2) | C13—C14 | 1.388 (3) |
N3—C26 | 1.403 (2) | C13—H13A | 0.9500 |
N3—C20 | 1.405 (2) | C14—C15 | 1.402 (3) |
N4—C26 | 1.304 (2) | C14—H14A | 0.9500 |
N4—C25 | 1.403 (2) | C15—C16 | 1.386 (3) |
C1—C10 | 1.379 (2) | C15—H15A | 0.9500 |
C1—C2 | 1.421 (2) | C16—C17 | 1.387 (3) |
C1—C11 | 1.489 (2) | C16—H16A | 0.9500 |
C2—C7 | 1.413 (2) | C20—C21 | 1.389 (2) |
C2—C3 | 1.422 (2) | C20—C25 | 1.399 (2) |
C3—C4 | 1.380 (2) | C21—C22 | 1.393 (3) |
C3—C18 | 1.448 (2) | C21—H21A | 0.9500 |
C4—C5 | 1.400 (2) | C22—C23 | 1.395 (3) |
C4—H4B | 0.9500 | C22—H22A | 0.9500 |
C5—C6 | 1.383 (2) | C23—C24 | 1.383 (3) |
C5—H5A | 0.9500 | C23—H23A | 0.9500 |
C6—C7 | 1.422 (2) | C24—C25 | 1.391 (2) |
C6—C26 | 1.446 (2) | C24—H24A | 0.9500 |
C7—C8 | 1.426 (2) | | |
| | | |
C11—N1—C18 | 126.34 (15) | C17—C12—N1 | 104.97 (15) |
C11—N1—C12 | 128.01 (15) | C14—C13—C12 | 115.98 (18) |
C18—N1—C12 | 105.62 (14) | C14—C13—H13A | 122.0 |
C18—N2—C17 | 104.68 (14) | C12—C13—H13A | 122.0 |
C19—N3—C26 | 126.20 (14) | C13—C14—C15 | 121.55 (18) |
C19—N3—C20 | 127.70 (14) | C13—C14—H14A | 119.2 |
C26—N3—C20 | 106.07 (13) | C15—C14—H14A | 119.2 |
C26—N4—C25 | 104.76 (14) | C16—C15—C14 | 121.97 (18) |
C10—C1—C2 | 120.49 (16) | C16—C15—H15A | 119.0 |
C10—C1—C11 | 118.55 (15) | C14—C15—H15A | 119.0 |
C2—C1—C11 | 120.94 (16) | C15—C16—C17 | 117.05 (18) |
C7—C2—C1 | 119.31 (15) | C15—C16—H16A | 121.5 |
C7—C2—C3 | 119.36 (15) | C17—C16—H16A | 121.5 |
C1—C2—C3 | 121.31 (15) | C16—C17—C12 | 120.72 (17) |
C4—C3—C2 | 119.85 (15) | C16—C17—N2 | 128.30 (17) |
C4—C3—C18 | 122.10 (15) | C12—C17—N2 | 110.98 (15) |
C2—C3—C18 | 118.05 (15) | N2—C18—N1 | 113.75 (15) |
C3—C4—C5 | 120.83 (16) | N2—C18—C3 | 127.46 (16) |
C3—C4—H4B | 119.6 | N1—C18—C3 | 118.78 (15) |
C5—C4—H4B | 119.6 | O2—C19—N3 | 121.03 (16) |
C6—C5—C4 | 120.56 (16) | O2—C19—C8 | 124.37 (16) |
C6—C5—H5A | 119.7 | N3—C19—C8 | 114.59 (14) |
C4—C5—H5A | 119.7 | C21—C20—C25 | 123.44 (16) |
C5—C6—C7 | 119.81 (15) | C21—C20—N3 | 131.97 (16) |
C5—C6—C26 | 122.51 (15) | C25—C20—N3 | 104.56 (14) |
C7—C6—C26 | 117.68 (15) | C20—C21—C22 | 115.89 (17) |
C2—C7—C6 | 119.54 (15) | C20—C21—H21A | 122.1 |
C2—C7—C8 | 118.71 (15) | C22—C21—H21A | 122.1 |
C6—C7—C8 | 121.75 (15) | C21—C22—C23 | 121.32 (17) |
C9—C8—C7 | 120.62 (16) | C21—C22—H22A | 119.3 |
C9—C8—C19 | 118.60 (15) | C23—C22—H22A | 119.3 |
C7—C8—C19 | 120.78 (15) | C24—C23—C22 | 121.98 (17) |
C8—C9—C10 | 120.36 (16) | C24—C23—H23A | 119.0 |
C8—C9—H9A | 119.8 | C22—C23—H23A | 119.0 |
C10—C9—H9A | 119.8 | C23—C24—C25 | 117.77 (17) |
C1—C10—C9 | 120.49 (16) | C23—C24—H24A | 121.1 |
C1—C10—H10A | 119.8 | C25—C24—H24A | 121.1 |
C9—C10—H10A | 119.8 | C24—C25—C20 | 119.57 (16) |
O1—C11—N1 | 121.73 (17) | C24—C25—N4 | 129.14 (16) |
O1—C11—C1 | 123.84 (17) | C20—C25—N4 | 111.30 (15) |
N1—C11—C1 | 114.43 (15) | N4—C26—N3 | 113.31 (15) |
C13—C12—C17 | 122.72 (17) | N4—C26—C6 | 127.72 (15) |
C13—C12—N1 | 132.31 (17) | N3—C26—C6 | 118.96 (15) |
| | | |
C10—C1—C2—C7 | 0.3 (2) | N1—C12—C17—C16 | 179.41 (16) |
C11—C1—C2—C7 | 178.79 (14) | C13—C12—C17—N2 | 179.05 (15) |
C10—C1—C2—C3 | −178.41 (16) | N1—C12—C17—N2 | −0.76 (19) |
C11—C1—C2—C3 | 0.1 (2) | C18—N2—C17—C16 | −179.52 (18) |
C7—C2—C3—C4 | −1.9 (2) | C18—N2—C17—C12 | 0.67 (19) |
C1—C2—C3—C4 | 176.75 (15) | C17—N2—C18—N1 | −0.31 (19) |
C7—C2—C3—C18 | 178.01 (14) | C17—N2—C18—C3 | 179.41 (16) |
C1—C2—C3—C18 | −3.3 (2) | C11—N1—C18—N2 | 177.90 (16) |
C2—C3—C4—C5 | 2.5 (3) | C12—N1—C18—N2 | −0.14 (19) |
C18—C3—C4—C5 | −177.47 (15) | C11—N1—C18—C3 | −1.9 (2) |
C3—C4—C5—C6 | −1.1 (3) | C12—N1—C18—C3 | −179.89 (14) |
C4—C5—C6—C7 | −0.8 (2) | C4—C3—C18—N2 | 4.4 (3) |
C4—C5—C6—C26 | −179.71 (15) | C2—C3—C18—N2 | −175.56 (16) |
C1—C2—C7—C6 | −178.63 (14) | C4—C3—C18—N1 | −175.92 (15) |
C3—C2—C7—C6 | 0.1 (2) | C2—C3—C18—N1 | 4.1 (2) |
C1—C2—C7—C8 | 0.8 (2) | C26—N3—C19—O2 | −179.87 (16) |
C3—C2—C7—C8 | 179.53 (14) | C20—N3—C19—O2 | −2.1 (3) |
C5—C6—C7—C2 | 1.3 (2) | C26—N3—C19—C8 | 0.9 (2) |
C26—C6—C7—C2 | −179.75 (14) | C20—N3—C19—C8 | 178.74 (15) |
C5—C6—C7—C8 | −178.17 (15) | C9—C8—C19—O2 | 2.0 (3) |
C26—C6—C7—C8 | 0.8 (2) | C7—C8—C19—O2 | −178.00 (16) |
C2—C7—C8—C9 | −1.5 (2) | C9—C8—C19—N3 | −178.80 (15) |
C6—C7—C8—C9 | 177.92 (15) | C7—C8—C19—N3 | 1.2 (2) |
C2—C7—C8—C19 | 178.52 (14) | C19—N3—C20—C21 | 4.0 (3) |
C6—C7—C8—C19 | −2.0 (2) | C26—N3—C20—C21 | −177.86 (17) |
C7—C8—C9—C10 | 1.1 (3) | C19—N3—C20—C25 | −177.90 (15) |
C19—C8—C9—C10 | −178.94 (16) | C26—N3—C20—C25 | 0.25 (17) |
C2—C1—C10—C9 | −0.7 (3) | C25—C20—C21—C22 | 2.1 (3) |
C11—C1—C10—C9 | −179.27 (15) | N3—C20—C21—C22 | 179.92 (16) |
C8—C9—C10—C1 | 0.0 (3) | C20—C21—C22—C23 | −0.8 (3) |
C18—N1—C11—O1 | 178.06 (16) | C21—C22—C23—C24 | −1.0 (3) |
C12—N1—C11—O1 | −4.3 (3) | C22—C23—C24—C25 | 1.4 (3) |
C18—N1—C11—C1 | −1.3 (2) | C23—C24—C25—C20 | −0.2 (3) |
C12—N1—C11—C1 | 176.29 (15) | C23—C24—C25—N4 | −179.75 (17) |
C10—C1—C11—O1 | 1.4 (3) | C21—C20—C25—C24 | −1.7 (3) |
C2—C1—C11—O1 | −177.17 (16) | N3—C20—C25—C24 | −179.97 (15) |
C10—C1—C11—N1 | −179.26 (15) | C21—C20—C25—N4 | 177.99 (15) |
C2—C1—C11—N1 | 2.2 (2) | N3—C20—C25—N4 | −0.34 (18) |
C11—N1—C12—C13 | 2.8 (3) | C26—N4—C25—C24 | 179.87 (17) |
C18—N1—C12—C13 | −179.25 (18) | C26—N4—C25—C20 | 0.28 (18) |
C11—N1—C12—C17 | −177.46 (16) | C25—N4—C26—N3 | −0.11 (18) |
C18—N1—C12—C17 | 0.53 (17) | C25—N4—C26—C6 | −179.84 (16) |
C17—C12—C13—C14 | 0.0 (3) | C19—N3—C26—N4 | 178.09 (15) |
N1—C12—C13—C14 | 179.79 (17) | C20—N3—C26—N4 | −0.10 (19) |
C12—C13—C14—C15 | 0.6 (3) | C19—N3—C26—C6 | −2.1 (2) |
C13—C14—C15—C16 | −0.6 (3) | C20—N3—C26—C6 | 179.66 (14) |
C14—C15—C16—C17 | −0.2 (3) | C5—C6—C26—N4 | −0.1 (3) |
C15—C16—C17—C12 | 0.8 (3) | C7—C6—C26—N4 | −179.10 (16) |
C15—C16—C17—N2 | −178.99 (17) | C5—C6—C26—N3 | −179.86 (15) |
C13—C12—C17—C16 | −0.8 (3) | C7—C6—C26—N3 | 1.2 (2) |
Crystal data top
C26H12N4O2 | Dx = 1.559 Mg m−3 |
Mr = 412.40 | Melting point: 741 K |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 16.971 (2) Å | Cell parameters from 1796 reflections |
b = 7.3707 (9) Å | θ = 2.6–72.3° |
c = 14.0809 (17) Å | µ = 0.83 mm−1 |
β = 94.09 (1)° | T = 130 K |
V = 1756.8 (4) Å3 | Plate, dark red |
Z = 4 | 0.14 × 0.08 × 0.01 mm |
F(000) = 848 | |
Data collection top
BRUKER AXS (Kappa APEX II Duo) diffractometer | 1498 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.0000 |
Graphite monochromator | θmax = 50.0°, θmin = 2.6° |
Absorption correction: empirical (using intensity measurements) R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38 | h = −16→16 |
Tmin = 0.890, Tmax = 0.989 | k = −7→7 |
1794 measured reflections | l = −13→13 |
1794 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.110 | H-atom parameters constrained |
wR(F2) = 0.321 | w = 1/[σ2(Fo2) + (0.1921P)2 + 7.3569P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.055 |
1794 reflections | Δρmax = 0.74 e Å−3 |
290 parameters | Δρmin = −0.53 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0037 (12) |
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.9318 (4) | 0.1829 (9) | 0.9837 (6) | 0.025 (2) | |
N3 | 0.5571 (4) | −0.1941 (10) | 0.9621 (6) | 0.030 (2) | |
C2 | 0.7827 (5) | 0.0397 (11) | 0.9767 (8) | 0.027 (2) | |
C1 | 0.8203 (5) | 0.0628 (12) | 0.8906 (7) | 0.027 (2) | |
C7 | 0.7053 (5) | −0.0487 (12) | 0.9727 (7) | 0.026 (2) | |
C3 | 0.8185 (5) | 0.0904 (12) | 1.0668 (7) | 0.029 (3) | |
O1 | 0.9374 (4) | 0.1650 (9) | 0.8231 (6) | 0.043 (2) | |
C6 | 0.6687 (5) | −0.0713 (11) | 1.0593 (6) | 0.023 (2) | |
N4 | 0.5446 (4) | −0.1890 (10) | 1.1219 (7) | 0.030 (2) | |
O2 | 0.5527 (4) | −0.2316 (10) | 0.8032 (6) | 0.044 (2) | |
C19 | 0.5917 (6) | −0.1767 (12) | 0.8761 (8) | 0.029 (3) | |
C26 | 0.5925 (5) | −0.1514 (12) | 1.0495 (8) | 0.025 (2) | |
C8 | 0.6699 (5) | −0.0953 (11) | 0.8841 (7) | 0.026 (2) | |
N2 | 0.9422 (4) | 0.2268 (10) | 1.1407 (5) | 0.025 (2) | |
C5 | 0.7076 (5) | −0.0181 (12) | 1.1476 (7) | 0.031 (3) | |
H5 | 0.6828 | −0.0405 | 1.2048 | 0.037* | |
C11 | 0.8975 (6) | 0.1380 (12) | 0.8933 (9) | 0.035 (3) | |
C18 | 0.8944 (5) | 0.1663 (11) | 1.0670 (7) | 0.027 (3) | |
C9 | 0.7082 (6) | −0.0681 (14) | 0.8010 (7) | 0.035 (3) | |
H9 | 0.6826 | −0.1026 | 0.7415 | 0.043* | |
C10 | 0.7810 (6) | 0.0066 (13) | 0.8035 (8) | 0.038 (3) | |
H10 | 0.8062 | 0.0217 | 0.7459 | 0.046* | |
C4 | 0.7793 (5) | 0.0640 (12) | 1.1520 (7) | 0.029 (3) | |
H4 | 0.8033 | 0.1037 | 1.2115 | 0.034* | |
C20 | 0.4830 (5) | −0.2732 (12) | 0.9790 (8) | 0.027 (3) | |
C22 | 0.3572 (6) | −0.4096 (12) | 0.9563 (9) | 0.036 (3) | |
H22 | 0.3151 | −0.4580 | 0.9159 | 0.044* | |
C14 | 1.1353 (5) | 0.3798 (13) | 0.9991 (8) | 0.033 (3) | |
H14 | 1.1798 | 0.4100 | 0.9649 | 0.040* | |
C15 | 1.1406 (6) | 0.4083 (13) | 1.0947 (8) | 0.036 (3) | |
H15 | 1.1878 | 0.4583 | 1.1241 | 0.043* | |
C21 | 0.4237 (6) | −0.3440 (12) | 0.9149 (8) | 0.034 (3) | |
H21 | 0.4286 | −0.3470 | 0.8481 | 0.041* | |
C23 | 0.3498 (6) | −0.4076 (13) | 1.0502 (8) | 0.034 (3) | |
H23 | 0.3032 | −0.4555 | 1.0741 | 0.041* | |
C17 | 1.0135 (6) | 0.2878 (12) | 1.1027 (8) | 0.036 (3) | |
C12 | 1.0069 (5) | 0.2655 (11) | 1.0051 (7) | 0.018 (2) | |
C25 | 0.4751 (6) | −0.2689 (13) | 1.0758 (7) | 0.028 (3) | |
C13 | 1.0685 (6) | 0.3088 (13) | 0.9477 (8) | 0.038 (3) | |
H13 | 1.0652 | 0.2917 | 0.8807 | 0.045* | |
C16 | 1.0794 (6) | 0.3666 (13) | 1.1503 (8) | 0.039 (3) | |
H16 | 1.0821 | 0.3901 | 1.2167 | 0.047* | |
C24 | 0.4092 (5) | −0.3364 (12) | 1.1147 (8) | 0.034 (3) | |
H24 | 0.4040 | −0.3351 | 1.1814 | 0.040* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.022 (4) | 0.014 (4) | 0.041 (6) | 0.003 (3) | 0.006 (4) | 0.002 (4) |
N3 | 0.027 (5) | 0.033 (5) | 0.029 (6) | −0.005 (4) | −0.011 (5) | −0.006 (4) |
C2 | 0.023 (5) | 0.018 (5) | 0.041 (7) | −0.006 (4) | 0.005 (5) | −0.001 (5) |
C1 | 0.019 (5) | 0.023 (5) | 0.038 (7) | 0.003 (4) | 0.002 (5) | 0.015 (5) |
C7 | 0.024 (5) | 0.022 (5) | 0.034 (7) | 0.003 (4) | 0.000 (5) | −0.010 (5) |
C3 | 0.016 (5) | 0.032 (6) | 0.039 (7) | 0.009 (4) | 0.012 (5) | 0.005 (5) |
O1 | 0.029 (4) | 0.052 (5) | 0.048 (5) | −0.003 (3) | 0.012 (4) | 0.009 (4) |
C6 | 0.027 (6) | 0.020 (5) | 0.021 (6) | 0.004 (4) | 0.004 (5) | −0.004 (5) |
N4 | 0.017 (4) | 0.026 (5) | 0.048 (6) | 0.001 (3) | 0.012 (4) | −0.002 (4) |
O2 | 0.040 (4) | 0.049 (5) | 0.042 (5) | −0.013 (4) | −0.006 (4) | −0.015 (4) |
C19 | 0.040 (6) | 0.017 (5) | 0.030 (7) | 0.006 (4) | 0.012 (6) | 0.010 (5) |
C26 | 0.011 (5) | 0.021 (5) | 0.046 (7) | 0.008 (4) | 0.011 (5) | 0.010 (5) |
C8 | 0.021 (5) | 0.021 (5) | 0.036 (7) | −0.009 (4) | 0.002 (5) | −0.001 (5) |
N2 | 0.024 (4) | 0.024 (4) | 0.025 (5) | 0.001 (4) | −0.005 (4) | −0.004 (4) |
C5 | 0.031 (6) | 0.028 (6) | 0.034 (7) | 0.005 (5) | 0.007 (5) | 0.010 (5) |
C11 | 0.025 (6) | 0.028 (6) | 0.051 (8) | −0.002 (5) | 0.010 (6) | 0.002 (5) |
C18 | 0.030 (6) | 0.018 (5) | 0.031 (7) | 0.006 (4) | 0.002 (6) | 0.002 (5) |
C9 | 0.034 (6) | 0.047 (7) | 0.025 (7) | −0.001 (5) | −0.003 (5) | −0.004 (5) |
C10 | 0.039 (7) | 0.043 (7) | 0.035 (7) | 0.000 (5) | 0.011 (5) | −0.003 (6) |
C4 | 0.016 (5) | 0.034 (6) | 0.036 (7) | −0.003 (4) | 0.001 (5) | −0.011 (5) |
C20 | 0.011 (5) | 0.020 (5) | 0.051 (9) | −0.013 (4) | 0.001 (5) | 0.001 (5) |
C22 | 0.026 (6) | 0.018 (5) | 0.067 (9) | 0.000 (4) | 0.016 (6) | 0.007 (6) |
C14 | 0.014 (5) | 0.031 (6) | 0.054 (8) | −0.001 (4) | 0.008 (5) | −0.002 (5) |
C15 | 0.025 (6) | 0.041 (6) | 0.041 (8) | 0.000 (5) | −0.007 (5) | −0.006 (6) |
C21 | 0.034 (6) | 0.027 (6) | 0.043 (7) | 0.010 (5) | 0.005 (5) | 0.008 (5) |
C23 | 0.018 (5) | 0.033 (6) | 0.052 (8) | 0.003 (5) | 0.013 (5) | 0.008 (5) |
C17 | 0.031 (6) | 0.025 (6) | 0.051 (9) | 0.000 (5) | 0.000 (6) | 0.014 (5) |
C12 | 0.017 (5) | 0.021 (5) | 0.017 (6) | −0.015 (4) | 0.004 (4) | −0.002 (4) |
C25 | 0.033 (7) | 0.029 (6) | 0.021 (7) | 0.016 (5) | 0.007 (5) | 0.001 (5) |
C13 | 0.043 (7) | 0.027 (6) | 0.044 (7) | 0.006 (5) | 0.005 (6) | −0.001 (5) |
C16 | 0.031 (6) | 0.039 (6) | 0.048 (7) | −0.003 (5) | 0.010 (6) | −0.008 (5) |
C24 | 0.021 (6) | 0.035 (6) | 0.044 (7) | 0.000 (4) | 0.002 (6) | −0.002 (5) |
Geometric parameters (Å, º) top
N1—C18 | 1.378 (13) | C5—H5 | 0.9500 |
N1—C11 | 1.401 (13) | C9—C10 | 1.351 (14) |
N1—C12 | 1.425 (11) | C9—H9 | 0.9500 |
N3—C26 | 1.368 (13) | C10—H10 | 0.9500 |
N3—C19 | 1.389 (14) | C4—H4 | 0.9500 |
N3—C20 | 1.421 (12) | C20—C25 | 1.379 (14) |
C2—C1 | 1.419 (14) | C20—C21 | 1.405 (14) |
C2—C3 | 1.417 (15) | C22—C23 | 1.336 (16) |
C2—C7 | 1.464 (13) | C22—C21 | 1.394 (14) |
C1—C10 | 1.417 (15) | C22—H22 | 0.9500 |
C1—C11 | 1.420 (13) | C14—C15 | 1.359 (15) |
C7—C8 | 1.389 (14) | C14—C13 | 1.403 (14) |
C7—C6 | 1.417 (14) | C14—H14 | 0.9500 |
C3—C18 | 1.405 (13) | C15—C16 | 1.379 (14) |
C3—C4 | 1.426 (14) | C15—H15 | 0.9500 |
O1—C11 | 1.254 (13) | C21—H21 | 0.9500 |
C6—C26 | 1.420 (13) | C23—C24 | 1.410 (15) |
C6—C5 | 1.420 (14) | C23—H23 | 0.9500 |
N4—C26 | 1.376 (13) | C17—C12 | 1.380 (15) |
N4—C25 | 1.432 (12) | C17—C16 | 1.389 (14) |
O2—C19 | 1.249 (13) | C12—C13 | 1.403 (13) |
C19—C8 | 1.453 (14) | C25—C24 | 1.372 (14) |
C8—C9 | 1.393 (15) | C13—H13 | 0.9500 |
N2—C18 | 1.347 (12) | C16—H16 | 0.9500 |
N2—C17 | 1.430 (13) | C24—H24 | 0.9500 |
C5—C4 | 1.357 (13) | | |
| | | |
C18—N1—C11 | 124.4 (8) | C8—C9—H9 | 119.4 |
C18—N1—C12 | 108.5 (8) | C9—C10—C1 | 121.0 (10) |
C11—N1—C12 | 126.9 (8) | C9—C10—H10 | 119.5 |
C26—N3—C19 | 125.3 (8) | C1—C10—H10 | 119.5 |
C26—N3—C20 | 106.3 (8) | C5—C4—C3 | 119.5 (9) |
C19—N3—C20 | 128.2 (8) | C5—C4—H4 | 120.3 |
C1—C2—C3 | 122.9 (8) | C3—C4—H4 | 120.3 |
C1—C2—C7 | 118.6 (9) | C25—C20—C21 | 121.8 (9) |
C3—C2—C7 | 118.5 (9) | C25—C20—N3 | 107.9 (8) |
C2—C1—C10 | 119.4 (8) | C21—C20—N3 | 130.3 (10) |
C2—C1—C11 | 119.6 (10) | C23—C22—C21 | 123.1 (11) |
C10—C1—C11 | 120.9 (10) | C23—C22—H22 | 118.5 |
C8—C7—C6 | 123.7 (8) | C21—C22—H22 | 118.5 |
C8—C7—C2 | 118.3 (9) | C15—C14—C13 | 124.2 (10) |
C6—C7—C2 | 117.8 (9) | C15—C14—H14 | 117.9 |
C18—C3—C2 | 116.2 (9) | C13—C14—H14 | 117.9 |
C18—C3—C4 | 122.3 (9) | C14—C15—C16 | 121.9 (9) |
C2—C3—C4 | 121.5 (8) | C14—C15—H15 | 119.1 |
C7—C6—C26 | 114.7 (9) | C16—C15—H15 | 119.0 |
C7—C6—C5 | 121.1 (8) | C22—C21—C20 | 115.1 (10) |
C26—C6—C5 | 124.2 (9) | C22—C21—H21 | 122.4 |
C26—N4—C25 | 105.0 (8) | C20—C21—H21 | 122.4 |
O2—C19—N3 | 117.0 (8) | C22—C23—C24 | 121.9 (10) |
O2—C19—C8 | 128.7 (9) | C22—C23—H23 | 119.0 |
N3—C19—C8 | 114.3 (9) | C24—C23—H23 | 119.1 |
N3—C26—N4 | 112.0 (8) | C12—C17—C16 | 122.4 (9) |
N3—C26—C6 | 121.4 (9) | C12—C17—N2 | 108.9 (8) |
N4—C26—C6 | 126.5 (10) | C16—C17—N2 | 128.6 (10) |
C7—C8—C9 | 121.4 (8) | C17—C12—C13 | 122.4 (9) |
C7—C8—C19 | 120.5 (9) | C17—C12—N1 | 105.6 (8) |
C9—C8—C19 | 118.2 (9) | C13—C12—N1 | 131.8 (9) |
C18—N2—C17 | 107.1 (8) | C24—C25—C20 | 121.8 (10) |
C4—C5—C6 | 121.5 (9) | C24—C25—N4 | 129.4 (9) |
C4—C5—H5 | 119.2 | C20—C25—N4 | 108.8 (8) |
C6—C5—H5 | 119.3 | C14—C13—C12 | 113.3 (10) |
O1—C11—N1 | 117.8 (8) | C14—C13—H13 | 123.3 |
O1—C11—C1 | 126.2 (11) | C12—C13—H13 | 123.3 |
N1—C11—C1 | 116.0 (10) | C15—C16—C17 | 115.6 (10) |
N2—C18—N1 | 109.7 (8) | C15—C16—H16 | 122.2 |
N2—C18—C3 | 129.4 (9) | C17—C16—H16 | 122.2 |
N1—C18—C3 | 120.8 (9) | C25—C24—C23 | 116.3 (10) |
C10—C9—C8 | 121.2 (10) | C25—C24—H24 | 121.9 |
C10—C9—H9 | 119.4 | C23—C24—H24 | 121.8 |