3-(4-Bromo­phenyl)-2-(3,4-di­hydro-2H-pyran-5-yl)-1,1,1-tri­fluoro­propan-2-ol

Coles, S.J.; Hursthouse, M.B.

doi:10.1107/S0108270100010556

3-(4-Bromophenyl)-2-(3,4-dihydro-2H-pyran-5-yl)-1,1,1-trifluoropropan-2-ol

S. J. Coles and M. B. Hursthouse

The molecular structure of the title compound, C₁₄H₁₄BrF₃O₂, adopts a bent conformation. Intramolecular O-H

F and intermolecular O-H

O interactions form a bifurcated hydrogen bond which produces a supramolecular assembly of head-to-tail dimers.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100010556/qd0013sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S0108270100010556/qd0013Isup2.hkl Contains datablock I

CCDC reference: 150739

Computing details top

Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).

(I) top

Crystal data top

C₁₄H₁₄BrF₃O₂	Z = 2
M_r = 351.16	F(000) = 352
Triclinic, P1	D_x = 1.627 Mg m⁻³
a = 7.9539 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.5523 (19) Å	Cell parameters from 5354 reflections
c = 10.695 (2) Å	θ = 2.7–27.5°
α = 97.61 (3)°	µ = 2.90 mm⁻¹
β = 110.44 (3)°	T = 298 K
γ = 104.17 (3)°	Block, colourless
V = 716.7 (2) Å³	0.35 × 0.35 × 0.35 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	1389 reflections with I > 2σ(I)
Radiation source: Nonius FR591 rotating anode	R_int = 0.049
φ and ω scans to fill Ewald sphere	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scans (Blessing, 1995)	h = −10→10
T_min = 0.331, T_max = 0.379	k = −12→12
5354 measured reflections	l = −13→13
2944 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0791P)² + 0.1443P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.058	(Δ/σ)_max = 0.002
wR(F²) = 0.180	Δρ_max = 0.44 e Å⁻³
S = 1.00	Δρ_min = −0.55 e Å⁻³
2944 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
182 parameters	Extinction coefficient: 0.015 (4)
0 restraints

Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.07811 (11)	0.90437 (9)	0.86045 (10)	0.1296 (5)
F1	0.7830 (4)	1.4658 (4)	0.5278 (3)	0.0913 (10)
F2	0.9383 (5)	1.3107 (4)	0.5512 (3)	0.1000 (11)
F3	1.0410 (4)	1.5164 (4)	0.7034 (3)	0.0863 (9)
O1	0.9008 (4)	1.2645 (4)	0.7862 (3)	0.0625 (8)
H1	0.9994	1.329	0.8383	0.094*
O2	0.7349 (4)	1.5466 (4)	1.0032 (3)	0.0631 (9)
C1	0.2376 (8)	0.9932 (6)	0.7779 (6)	0.0767 (14)
C2	0.1812 (7)	1.0789 (6)	0.6893 (6)	0.0820 (15)
H2	0.0629	1.0918	0.6675	0.098*
C3	0.3005 (6)	1.1464 (6)	0.6320 (5)	0.0707 (13)
H3	0.2606	1.2045	0.5715	0.085*
C4	0.4785 (6)	1.1304 (5)	0.6621 (5)	0.0615 (12)
C5	0.5295 (7)	1.0409 (6)	0.7520 (5)	0.0728 (13)
H5	0.6467	1.026	0.7738	0.087*
C6	0.4128 (8)	0.9750 (6)	0.8084 (6)	0.0811 (15)
H6	0.4515	0.9165	0.8688	0.097*
C7	0.6056 (6)	1.2037 (6)	0.5992 (4)	0.0647 (12)
H7a	0.534	1.2421	0.5258	0.078*
H7b	0.6479	1.1296	0.5585	0.078*
C8	0.7787 (6)	1.3309 (5)	0.7008 (4)	0.0539 (11)
C9	0.8855 (7)	1.4075 (7)	0.6214 (5)	0.0702 (14)
C10	0.7274 (5)	1.4448 (5)	0.7832 (4)	0.0487 (10)
C11	0.7696 (5)	1.4510 (5)	0.9150 (4)	0.0541 (11)
H11	0.8286	1.3842	0.9515	0.065*
C12	0.6541 (7)	1.6537 (6)	0.9450 (5)	0.0723 (14)
H12a	0.7541	1.7379	0.9483	0.087*
H12b	0.5913	1.6895	0.9995	0.087*
C13	0.5151 (7)	1.5888 (6)	0.7994 (5)	0.0741 (14)
H13a	0.4615	1.6633	0.7637	0.089*
H13b	0.4131	1.5059	0.7957	0.089*
C14	0.6129 (6)	1.5358 (6)	0.7124 (4)	0.0630 (12)
H14a	0.5194	1.4764	0.6231	0.076*
H14b	0.6945	1.6207	0.6986	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1237 (7)	0.1057 (7)	0.1764 (9)	0.0111 (5)	0.0962 (6)	0.0336 (6)
F1	0.0766 (18)	0.154 (3)	0.0668 (17)	0.049 (2)	0.0368 (15)	0.057 (2)
F2	0.101 (2)	0.143 (3)	0.093 (2)	0.058 (2)	0.0676 (19)	0.032 (2)
F3	0.0562 (16)	0.115 (3)	0.087 (2)	0.0144 (18)	0.0321 (15)	0.0345 (19)
O1	0.0540 (16)	0.078 (2)	0.0567 (17)	0.0314 (17)	0.0175 (15)	0.0126 (17)
O2	0.0590 (18)	0.089 (2)	0.0445 (16)	0.0315 (18)	0.0209 (14)	0.0103 (16)
C1	0.076 (3)	0.055 (3)	0.092 (4)	0.009 (3)	0.039 (3)	0.000 (3)
C2	0.053 (3)	0.074 (4)	0.105 (4)	0.008 (3)	0.030 (3)	0.000 (3)
C3	0.053 (3)	0.072 (3)	0.075 (3)	0.017 (3)	0.017 (2)	0.004 (3)
C4	0.054 (2)	0.061 (3)	0.057 (3)	0.011 (2)	0.020 (2)	−0.008 (3)
C5	0.067 (3)	0.072 (3)	0.076 (3)	0.026 (3)	0.025 (3)	0.007 (3)
C6	0.094 (4)	0.064 (3)	0.091 (4)	0.027 (3)	0.043 (3)	0.015 (3)
C7	0.056 (3)	0.076 (3)	0.052 (2)	0.021 (3)	0.017 (2)	−0.001 (2)
C8	0.050 (2)	0.070 (3)	0.045 (2)	0.024 (2)	0.018 (2)	0.015 (2)
C9	0.055 (3)	0.104 (4)	0.059 (3)	0.031 (3)	0.026 (2)	0.020 (3)
C10	0.040 (2)	0.064 (3)	0.041 (2)	0.014 (2)	0.0153 (17)	0.012 (2)
C11	0.040 (2)	0.071 (3)	0.048 (2)	0.019 (2)	0.0142 (19)	0.011 (2)
C12	0.066 (3)	0.076 (4)	0.072 (3)	0.027 (3)	0.025 (3)	0.006 (3)
C13	0.069 (3)	0.086 (4)	0.070 (3)	0.042 (3)	0.021 (3)	0.013 (3)
C14	0.061 (3)	0.073 (3)	0.054 (2)	0.025 (3)	0.018 (2)	0.016 (2)

Geometric parameters (Å, º) top

Br1—C1	1.887 (6)	C4—C5	1.391 (7)
F1—C9	1.333 (5)	C4—C7	1.489 (7)
F2—C9	1.349 (6)	C5—C6	1.352 (7)
F3—C9	1.324 (6)	C7—C8	1.530 (6)
O1—C8	1.420 (5)	C8—C10	1.530 (6)
O2—C11	1.370 (5)	C8—C9	1.530 (6)
O2—C12	1.435 (6)	C10—C11	1.319 (6)
C1—C2	1.363 (8)	C10—C14	1.497 (6)
C1—C6	1.376 (8)	C12—C13	1.496 (7)
C2—C3	1.379 (7)	C13—C14	1.517 (6)
C3—C4	1.390 (6)

C11—O2—C12	115.2 (3)	C7—C8—C9	108.8 (4)
C2—C1—C6	119.4 (5)	C10—C8—C9	109.9 (4)
C2—C1—Br1	120.0 (4)	F3—C9—F1	106.8 (5)
C6—C1—Br1	120.6 (5)	F3—C9—F2	106.9 (4)
C1—C2—C3	119.6 (5)	F1—C9—F2	105.5 (4)
C2—C3—C4	122.0 (5)	F3—C9—C8	112.3 (4)
C3—C4—C5	116.5 (5)	F1—C9—C8	113.4 (4)
C3—C4—C7	121.4 (5)	F2—C9—C8	111.4 (5)
C5—C4—C7	122.1 (4)	C11—C10—C14	120.4 (4)
C6—C5—C4	121.6 (5)	C11—C10—C8	118.8 (4)
C5—C6—C1	121.0 (5)	C14—C10—C8	120.4 (3)
C4—C7—C8	113.9 (4)	C10—C11—O2	126.2 (4)
O1—C8—C7	106.6 (4)	O2—C12—C13	111.7 (4)
O1—C8—C10	112.5 (3)	C12—C13—C14	109.8 (4)
C7—C8—C10	112.8 (3)	C10—C14—C13	109.4 (4)
O1—C8—C9	106.0 (3)

C6—C1—C2—C3	−0.2 (8)	C7—C8—C9—F1	60.7 (5)
Br1—C1—C2—C3	178.4 (4)	C10—C8—C9—F1	−63.2 (5)
C1—C2—C3—C4	−0.2 (8)	O1—C8—C9—F2	56.1 (5)
C2—C3—C4—C5	0.8 (7)	C7—C8—C9—F2	−58.1 (5)
C2—C3—C4—C7	179.8 (5)	C10—C8—C9—F2	178.0 (4)
C3—C4—C5—C6	−1.0 (7)	O1—C8—C10—C11	−11.6 (5)
C7—C4—C5—C6	180.0 (5)	C7—C8—C10—C11	109.0 (4)
C4—C5—C6—C1	0.6 (8)	C9—C8—C10—C11	−129.5 (4)
C2—C1—C6—C5	0.1 (8)	O1—C8—C10—C14	174.9 (4)
Br1—C1—C6—C5	−178.6 (4)	C7—C8—C10—C14	−64.5 (5)
C3—C4—C7—C8	110.2 (5)	C9—C8—C10—C14	57.1 (5)
C5—C4—C7—C8	−70.8 (6)	C14—C10—C11—O2	−7.0 (7)
C4—C7—C8—O1	72.2 (4)	C8—C10—C11—O2	179.5 (4)
C4—C7—C8—C10	−51.7 (5)	C12—O2—C11—C10	−3.5 (6)
C4—C7—C8—C9	−173.9 (4)	C11—O2—C12—C13	37.4 (5)
O1—C8—C9—F3	−63.8 (5)	O2—C12—C13—C14	−60.4 (6)
C7—C8—C9—F3	−178.0 (4)	C11—C10—C14—C13	−16.6 (6)
C10—C8—C9—F3	58.0 (5)	C8—C10—C14—C13	156.7 (4)
O1—C8—C9—F1	175.0 (4)	C12—C13—C14—C10	48.1 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···F3	0.82	2.47	2.785 (4)	103.7
O1—H1···O2ⁱ	0.82	2.12	2.921 (5)	166.0

Symmetry code: (i) −x+2, −y+3, −z+2.

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3-(4-Bromo­phenyl)-2-(3,4-di­hydro-2H-pyran-5-yl)-1,1,1-tri­fluoro­propan-2-ol

Supporting information

3-(4-Bromophenyl)-2-(3,4-dihydro-2H-pyran-5-yl)-1,1,1-trifluoropropan-2-ol