2-[1-(4-Bromo-phen-yl)-3-hy-droxy-3-(4-meth-oxy-phen-yl)prop-yl]cyclo-hexa-nol.

In the title compound, C22H27BrO3, the cyclo-hexane ring adopts a chair conformation. The dihedral angle between the benzene rings is 41.9 (4)°. In the crystal, mol-ecules are linked by O-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network. In addition, π-π stacking inter-actions [centroid-centroid distance = 3.953 (6) Å] between the benzene rings of the meth-oxy-benzene groups occur.

Related literature

For the biological properties of 1,5-diols, see: Flamme & Roush (2005 ▶); Hansen et al. (2003 ▶); Huang et al. (2009 ▶); Oger et al. (2010 ▶). For details of the synthesis, see: Ceylan & Gezegen (2008 ▶); Gezegen et al. (2010 ▶). For ring conformation analysis, see: Cremer & Pople (1975 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H27BrO3

M = 419.34

Monoclinic,

a = 23.2993 (14) Å

b = 10.9282 (5) Å

c = 22.3632 (11) Å

β = 133.032 (3)°

V = 4162.2 (4) Å3

Z = 8

Mo Kα radiation

μ = 1.99 mm−1

T = 296 K

0.60 × 0.34 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration [X-RED32 (Stoe & Cie, 2002 ▶) and XABS2 (Parkin et al., 1995 ▶)] T min = 0.448, T max = 0.572

4301 measured reflections

4301 independent reflections

2327 reflections with I > 2σ(I)

R int = 0.000

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.198

S = 1.03

4301 reflections

240 parameters

149 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.78 e Å−3

Δρmin = −0.56 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813015869/sj5331sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813015869/sj5331Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813015869/sj5331Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H27BrO3	F(000) = 1744
Mr = 419.34	Dx = 1.338 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 538 reflections
a = 23.2993 (14) Å	θ = 1.8–28.0°
b = 10.9282 (5) Å	µ = 1.99 mm−1
c = 22.3632 (11) Å	T = 296 K
β = 133.032 (3)°	Prism, colourless
V = 4162.2 (4) Å3	0.60 × 0.34 × 0.28 mm
Z = 8

Stoe IPDS 2 diffractometer	4301 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2327 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.000
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.0°
ω scans	h = −29→21
Absorption correction: integration [X-RED32 (Stoe & Cie, 2002) and XABS2 (Parkin et al., 1995)]	k = 0→13
Tmin = 0.448, Tmax = 0.572	l = 0→28
4301 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0945P)2 + 0.8672P] where P = (Fo2 + 2Fc2)/3
4301 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.78 e Å−3
149 restraints	Δρmin = −0.56 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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.

	x	y	z	Uiso*/Ueq
Br1	0.90669 (5)	0.12894 (8)	0.49681 (4)	0.1178 (4)
O1	0.68319 (18)	0.2009 (3)	−0.02218 (19)	0.0645 (10)
O2	0.91572 (17)	0.3614 (3)	0.19089 (19)	0.0594 (10)
O3	0.9041 (4)	0.9462 (3)	0.2060 (3)	0.130 (3)
C1	0.7850 (3)	0.2963 (4)	0.2729 (3)	0.0658 (16)
C2	0.8135 (3)	0.2666 (5)	0.3495 (3)	0.0762 (19)
C3	0.8642 (3)	0.1688 (5)	0.3903 (3)	0.0678 (16)
C4	0.8854 (3)	0.1024 (4)	0.3576 (3)	0.0664 (16)
C5	0.8566 (3)	0.1340 (4)	0.2812 (3)	0.0579 (16)
C6	0.8059 (2)	0.2320 (4)	0.2374 (2)	0.0479 (11)
C7	0.7740 (2)	0.2639 (4)	0.1536 (2)	0.0494 (12)
C8	0.6854 (2)	0.2325 (4)	0.0871 (2)	0.0548 (14)
C9	0.6696 (3)	0.0990 (5)	0.0910 (3)	0.0761 (16)
C10	0.5823 (3)	0.0706 (6)	0.0323 (3)	0.090 (2)
C11	0.5419 (3)	0.1067 (5)	−0.0550 (3)	0.0787 (18)
C12	0.5591 (3)	0.2377 (5)	−0.0597 (3)	0.0705 (16)
C13	0.6465 (2)	0.2654 (4)	0.0002 (2)	0.0565 (14)
C14	0.7910 (2)	0.3971 (4)	0.1491 (2)	0.0542 (12)
C15	0.8779 (2)	0.4304 (4)	0.2098 (2)	0.0541 (12)
C16	0.8874 (3)	0.5678 (4)	0.2089 (3)	0.0542 (12)
C17	0.8778 (4)	0.6232 (5)	0.1470 (4)	0.092 (3)
C18	0.8820 (5)	0.7492 (5)	0.1436 (4)	0.108 (3)
C19	0.8971 (4)	0.8204 (4)	0.2031 (4)	0.087 (3)
C20	0.9063 (4)	0.7675 (4)	0.2643 (4)	0.088 (2)
C21	0.9017 (3)	0.6423 (4)	0.2674 (3)	0.0690 (19)
C22	0.8947 (6)	1.0051 (5)	0.1428 (6)	0.146 (5)
H1	0.75060	0.36190	0.24470	0.0790*
H1A	0.65010	0.16080	−0.06370	0.0970*
H2	0.79880	0.31140	0.37260	0.0910*
H2A	0.9441 (7)	0.398 (3)	0.1907 (8)	0.0890*
H4	0.91900	0.03590	0.38580	0.0800*
H5	0.87170	0.08820	0.25880	0.0700*
H7	0.80120	0.21210	0.14380	0.0600*
H8	0.65930	0.28140	0.09940	0.0660*
H9A	0.69390	0.07980	0.14630	0.0910*
H9B	0.69360	0.04740	0.07780	0.0910*
H10A	0.55890	0.11540	0.04870	0.1080*
H10B	0.57480	−0.01610	0.03430	0.1080*
H11A	0.55980	0.05310	−0.07400	0.0950*
H11B	0.48570	0.09600	−0.09090	0.0950*
H12A	0.53430	0.29160	−0.04850	0.0850*
H12B	0.53620	0.25450	−0.11480	0.0850*
H13	0.65320	0.35340	−0.00170	0.0670*
H14A	0.76880	0.41340	0.09420	0.0650*
H14B	0.76450	0.44980	0.15880	0.0650*
H15	0.90090	0.40710	0.26470	0.0650*
H17	0.86820	0.57490	0.10680	0.1100*
H18	0.87460	0.78490	0.10100	0.1280*
H20	0.91570	0.81630	0.30430	0.1050*
H21	0.90830	0.60750	0.30980	0.0830*
H22A	0.93450	0.97650	0.14400	0.2190*
H22B	0.89960	1.09200	0.15120	0.2190*
H22C	0.84380	0.98630	0.09060	0.2190*

	U11	U22	U33	U12	U13	U23
Br1	0.1390 (7)	0.1527 (7)	0.0648 (4)	−0.0010 (5)	0.0707 (5)	0.0173 (4)
O1	0.0527 (17)	0.092 (2)	0.0556 (17)	−0.0169 (16)	0.0396 (15)	−0.0152 (16)
O2	0.0511 (17)	0.0657 (18)	0.0653 (18)	−0.0043 (14)	0.0412 (15)	−0.0047 (14)
O3	0.260 (6)	0.060 (2)	0.194 (5)	0.006 (3)	0.204 (5)	0.002 (3)
C1	0.075 (3)	0.075 (3)	0.060 (2)	0.008 (2)	0.051 (3)	0.002 (2)
C2	0.095 (4)	0.084 (3)	0.071 (3)	0.001 (3)	0.065 (3)	−0.008 (3)
C3	0.071 (3)	0.076 (3)	0.053 (2)	−0.011 (2)	0.041 (2)	−0.003 (2)
C4	0.062 (3)	0.066 (3)	0.057 (2)	0.003 (2)	0.035 (2)	0.010 (2)
C5	0.055 (3)	0.063 (3)	0.056 (2)	0.002 (2)	0.038 (2)	0.000 (2)
C6	0.042 (2)	0.056 (2)	0.0412 (19)	−0.0040 (17)	0.0266 (18)	−0.0032 (17)
C7	0.046 (2)	0.060 (2)	0.045 (2)	−0.0022 (18)	0.0321 (19)	−0.0002 (18)
C8	0.040 (2)	0.078 (3)	0.046 (2)	−0.003 (2)	0.0292 (18)	0.000 (2)
C9	0.061 (3)	0.091 (3)	0.056 (2)	−0.026 (3)	0.032 (2)	0.006 (2)
C10	0.061 (3)	0.139 (5)	0.057 (3)	−0.037 (3)	0.035 (3)	−0.002 (3)
C11	0.048 (3)	0.125 (4)	0.055 (2)	−0.022 (3)	0.032 (2)	−0.005 (3)
C12	0.046 (2)	0.106 (4)	0.050 (2)	0.001 (2)	0.029 (2)	0.005 (2)
C13	0.045 (2)	0.075 (3)	0.046 (2)	−0.0012 (19)	0.0297 (19)	0.0007 (19)
C14	0.053 (2)	0.058 (2)	0.048 (2)	0.0022 (19)	0.033 (2)	0.0056 (18)
C15	0.053 (2)	0.062 (2)	0.047 (2)	−0.005 (2)	0.034 (2)	−0.0005 (19)
C16	0.057 (2)	0.059 (2)	0.053 (2)	−0.006 (2)	0.040 (2)	−0.0039 (19)
C17	0.159 (6)	0.068 (3)	0.101 (4)	−0.007 (3)	0.109 (4)	−0.002 (3)
C18	0.209 (7)	0.065 (3)	0.135 (5)	0.006 (4)	0.151 (6)	0.013 (3)
C19	0.147 (6)	0.053 (3)	0.127 (5)	0.002 (3)	0.119 (5)	−0.001 (3)
C20	0.140 (5)	0.063 (3)	0.099 (4)	−0.005 (3)	0.097 (4)	−0.011 (3)
C21	0.093 (4)	0.064 (3)	0.068 (3)	0.001 (2)	0.062 (3)	0.000 (2)
C22	0.287 (12)	0.068 (4)	0.227 (9)	0.018 (5)	0.232 (10)	0.028 (5)

Br1—C3	1.904 (5)	C19—C20	1.361 (11)
O1—C13	1.436 (7)	C20—C21	1.378 (6)
O2—C15	1.426 (7)	C1—H1	0.9300
O3—C19	1.381 (6)	C2—H2	0.9300
O3—C22	1.427 (13)	C4—H4	0.9300
O1—H1A	0.8200	C5—H5	0.9300
O2—H2A	0.78 (3)	C7—H7	0.9800
C1—C2	1.389 (8)	C8—H8	0.9800
C1—C6	1.374 (9)	C9—H9A	0.9700
C2—C3	1.378 (8)	C9—H9B	0.9700
C3—C4	1.341 (10)	C10—H10A	0.9700
C4—C5	1.387 (8)	C10—H10B	0.9700
C5—C6	1.387 (7)	C11—H11A	0.9700
C6—C7	1.512 (5)	C11—H11B	0.9700
C7—C8	1.550 (6)	C12—H12A	0.9700
C7—C14	1.530 (6)	C12—H12B	0.9700
C8—C9	1.522 (7)	C13—H13	0.9800
C8—C13	1.524 (5)	C14—H14A	0.9700
C9—C10	1.521 (10)	C14—H14B	0.9700
C10—C11	1.531 (7)	C15—H15	0.9800
C11—C12	1.510 (8)	C17—H17	0.9300
C12—C13	1.520 (8)	C18—H18	0.9300
C14—C15	1.524 (7)	C20—H20	0.9300
C15—C16	1.520 (6)	C21—H21	0.9300
C16—C21	1.375 (8)	C22—H22A	0.9600
C16—C17	1.382 (10)	C22—H22B	0.9600
C17—C18	1.386 (8)	C22—H22C	0.9600
C18—C19	1.364 (10)
C19—O3—C22	118.0 (6)	C14—C7—H7	107.00
C13—O1—H1A	110.00	C7—C8—H8	107.00
C15—O2—H2A	116 (2)	C9—C8—H8	107.00
C2—C1—C6	122.2 (5)	C13—C8—H8	107.00
C1—C2—C3	118.1 (6)	C8—C9—H9A	109.00
Br1—C3—C2	119.0 (5)	C8—C9—H9B	109.00
Br1—C3—C4	119.2 (4)	C10—C9—H9A	109.00
C2—C3—C4	121.8 (5)	C10—C9—H9B	109.00
C3—C4—C5	119.2 (5)	H9A—C9—H9B	108.00
C4—C5—C6	121.7 (6)	C9—C10—H10A	110.00
C5—C6—C7	121.0 (5)	C9—C10—H10B	110.00
C1—C6—C5	117.0 (4)	C11—C10—H10A	110.00
C1—C6—C7	122.0 (4)	C11—C10—H10B	110.00
C6—C7—C14	111.8 (3)	H10A—C10—H10B	108.00
C6—C7—C8	110.2 (4)	C10—C11—H11A	109.00
C8—C7—C14	112.5 (3)	C10—C11—H11B	109.00
C7—C8—C13	114.5 (4)	C12—C11—H11A	109.00
C7—C8—C9	111.9 (4)	C12—C11—H11B	109.00
C9—C8—C13	110.0 (3)	H11A—C11—H11B	108.00
C8—C9—C10	112.3 (5)	C11—C12—H12A	109.00
C9—C10—C11	110.1 (6)	C11—C12—H12B	109.00
C10—C11—C12	111.8 (4)	C13—C12—H12A	109.00
C11—C12—C13	112.8 (5)	C13—C12—H12B	109.00
O1—C13—C12	110.7 (4)	H12A—C12—H12B	108.00
O1—C13—C8	110.6 (4)	O1—C13—H13	108.00
C8—C13—C12	110.5 (5)	C8—C13—H13	108.00
C7—C14—C15	114.5 (3)	C12—C13—H13	108.00
O2—C15—C16	113.2 (5)	C7—C14—H14A	109.00
C14—C15—C16	109.9 (4)	C7—C14—H14B	108.00
O2—C15—C14	108.9 (3)	C15—C14—H14A	109.00
C17—C16—C21	117.5 (5)	C15—C14—H14B	109.00
C15—C16—C17	121.4 (5)	H14A—C14—H14B	108.00
C15—C16—C21	121.0 (5)	O2—C15—H15	108.00
C16—C17—C18	121.4 (7)	C14—C15—H15	108.00
C17—C18—C19	119.6 (8)	C16—C15—H15	108.00
O3—C19—C20	116.3 (6)	C16—C17—H17	119.00
O3—C19—C18	123.9 (7)	C18—C17—H17	119.00
C18—C19—C20	119.8 (5)	C17—C18—H18	120.00
C19—C20—C21	120.5 (6)	C19—C18—H18	120.00
C16—C21—C20	121.1 (6)	C19—C20—H20	120.00
C2—C1—H1	119.00	C21—C20—H20	120.00
C6—C1—H1	119.00	C16—C21—H21	119.00
C1—C2—H2	121.00	C20—C21—H21	119.00
C3—C2—H2	121.00	O3—C22—H22A	109.00
C3—C4—H4	120.00	O3—C22—H22B	110.00
C5—C4—H4	120.00	O3—C22—H22C	110.00
C4—C5—H5	119.00	H22A—C22—H22B	109.00
C6—C5—H5	119.00	H22A—C22—H22C	109.00
C6—C7—H7	107.00	H22B—C22—H22C	109.00
C8—C7—H7	107.00
C22—O3—C19—C20	−179.9 (10)	C9—C8—C13—C12	56.1 (6)
C22—O3—C19—C18	0.2 (16)	C7—C8—C13—O1	60.3 (5)
C2—C1—C6—C5	0.7 (9)	C7—C8—C13—C12	−176.9 (4)
C2—C1—C6—C7	179.3 (6)	C8—C9—C10—C11	55.8 (7)
C6—C1—C2—C3	−0.2 (10)	C9—C10—C11—C12	−53.1 (8)
C1—C2—C3—Br1	178.1 (5)	C10—C11—C12—C13	53.9 (8)
C1—C2—C3—C4	−0.7 (10)	C11—C12—C13—C8	−55.2 (6)
Br1—C3—C4—C5	−177.8 (5)	C11—C12—C13—O1	67.6 (6)
C2—C3—C4—C5	1.1 (10)	C7—C14—C15—C16	−171.5 (4)
C3—C4—C5—C6	−0.5 (10)	C7—C14—C15—O2	64.0 (5)
C4—C5—C6—C7	−179.0 (5)	O2—C15—C16—C17	44.5 (8)
C4—C5—C6—C1	−0.4 (9)	C14—C15—C16—C21	98.9 (7)
C5—C6—C7—C8	109.2 (6)	O2—C15—C16—C21	−139.1 (6)
C1—C6—C7—C8	−69.4 (6)	C14—C15—C16—C17	−77.5 (9)
C1—C6—C7—C14	56.5 (7)	C15—C16—C21—C20	−176.6 (7)
C5—C6—C7—C14	−125.0 (5)	C17—C16—C21—C20	0.0 (12)
C14—C7—C8—C9	178.6 (4)	C15—C16—C17—C18	176.3 (8)
C14—C7—C8—C13	52.5 (5)	C21—C16—C17—C18	−0.3 (13)
C6—C7—C14—C15	59.2 (6)	C16—C17—C18—C19	1.0 (16)
C8—C7—C14—C15	−176.3 (4)	C17—C18—C19—C20	−1.4 (16)
C6—C7—C8—C9	−56.0 (5)	C17—C18—C19—O3	178.5 (10)
C6—C7—C8—C13	177.9 (4)	O3—C19—C20—C21	−178.9 (9)
C13—C8—C9—C10	−57.8 (7)	C18—C19—C20—C21	1.0 (15)
C7—C8—C9—C10	173.7 (5)	C19—C20—C21—C16	−0.3 (14)
C9—C8—C13—O1	−66.8 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.82	2.13	2.854 (4)	147
O2—H2A···O2ii	0.78 (3)	2.46 (2)	2.871 (6)	115 (2)
C5—H5···O3iii	0.93	2.36	3.287 (10)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.82	2.13	2.854 (4)	147
O2—H2A⋯O2ii	0.78 (3)	2.46 (2)	2.871 (6)	115 (2)
C5—H5⋯O3iii	0.93	2.36	3.287 (10)	171

Symmetry codes: (i) ; (ii) ; (iii) .