4,4'-(Cyclo-hexane-1,1-di-yl)diphenol methanol solvate.

The title compound, crystallized as a methanol solvate, C(18)H(20)O(2)·CH(3)OH, is an inter-mediate in the synthesis of the anti-lipidemic agent clinofibrate. Mol-ecules are packed together with the methanol solvent molecule via two O-H⋯O hydrogen bonds. The third O-H⋯O hydrogen bond is between neighboring 4,4'-(cyclo-hexane-1,1-di-yl)diphenol mol-ecules. The dihedral angle between two benzene rings planes is 81.69 (6).

Related literature

For details of the anti-lipidemic agent clinofibrate, see: Nishizawa et al. (1993 ▶). For the synthesis of clinofibrate, see: Zimmerman et al. (1974 ▶). For a similar structure, see: Nassimbeni et al. (2007 ▶).

Experimental

Crystal data

C18H20O2·CH4O

M = 300.38

Triclinic,

a = 6.2245 (12) Å

b = 10.889 (2) Å

c = 12.712 (3) Å

α = 90.02 (3)°

β = 100.82 (3)°

γ = 90.03 (3)°

V = 846.3 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 113 (2) K

0.16 × 0.12 × 0.08 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.988, T max = 0.994

8706 measured reflections

2946 independent reflections

2042 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.182

S = 1.08

2946 reflections

203 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809000427/bq2114sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809000427/bq2114Isup2.hkl

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

C18H20O2·CH4O	Z = 2
Mr = 300.38	F(000) = 324
Triclinic, P1	Dx = 1.179 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.2245 (12) Å	Cell parameters from 2488 reflections
b = 10.889 (2) Å	θ = 2.5–27.5°
c = 12.712 (3) Å	µ = 0.08 mm−1
α = 90.02 (3)°	T = 113 K
β = 100.82 (3)°	Block, colorless
γ = 90.03 (3)°	0.16 × 0.12 × 0.08 mm
V = 846.3 (3) Å3

Rigaku Saturn diffractometer	2946 independent reflections
Radiation source: rotating anode	2042 reflections with I > 2σ(I)
confocal	Rint = 0.042
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −7→7
Tmin = 0.988, Tmax = 0.994	k = −12→12
8706 measured reflections	l = −15→14

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.182	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.1196P)2] where P = (Fo2 + 2Fc2)/3
2946 reflections	(Δ/σ)max = 0.002
203 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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.

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 > σ(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.

	x	y	z	Uiso*/Ueq
O1	0.6975 (2)	0.24041 (13)	0.37035 (12)	0.0310 (4)
H1	0.6022	0.1903	0.3764	0.046*
O2	0.4365 (3)	1.08574 (14)	0.39912 (12)	0.0299 (4)
H2	0.3199	1.1092	0.4133	0.045*
O3	0.1059 (3)	0.19930 (17)	0.49467 (14)	0.0468 (6)
H3	−0.0039	0.2132	0.4495	0.070*
C1	0.4012 (3)	0.69382 (19)	0.01335 (15)	0.0191 (5)
H1A	0.3732	0.6162	−0.0242	0.023*
H1B	0.5580	0.7033	0.0361	0.023*
C2	0.3017 (3)	0.80790 (19)	−0.06599 (15)	0.0210 (5)
H2A	0.3550	0.8835	−0.0299	0.025*
H2B	0.3662	0.8022	−0.1296	0.025*
C3	0.0496 (3)	0.8225 (2)	−0.10442 (16)	0.0239 (5)
H3A	0.0202	0.8974	−0.1459	0.029*
H3B	−0.0058	0.7540	−0.1504	0.029*
C4	−0.0694 (3)	0.82727 (19)	−0.00891 (16)	0.0219 (5)
H4A	−0.2261	0.8184	−0.0325	0.026*
H4B	−0.0401	0.9041	0.0298	0.026*
C5	0.0328 (3)	0.70978 (18)	0.06654 (15)	0.0199 (5)
H5A	−0.0402	0.7085	0.1276	0.024*
H5B	−0.0124	0.6360	0.0255	0.024*
C6	0.2867 (3)	0.69626 (18)	0.11244 (15)	0.0164 (5)
C7	0.3890 (3)	0.57198 (18)	0.18020 (15)	0.0168 (5)
C8	0.2680 (3)	0.48381 (18)	0.19927 (16)	0.0212 (5)
H8	0.1178	0.4869	0.1743	0.025*
C9	0.3686 (3)	0.37378 (19)	0.26271 (15)	0.0228 (5)
H9	0.2704	0.3129	0.2738	0.027*
C10	0.5952 (3)	0.34952 (19)	0.30856 (15)	0.0205 (5)
C11	0.7200 (3)	0.43517 (19)	0.29044 (16)	0.0206 (5)
H11	0.8703	0.4310	0.3149	0.025*
C12	0.6166 (3)	0.54470 (18)	0.22754 (15)	0.0202 (5)
H12	0.7154	0.6056	0.2171	0.024*
C13	0.3242 (3)	0.80415 (17)	0.18613 (15)	0.0161 (5)
C14	0.2027 (3)	0.83272 (18)	0.26803 (15)	0.0201 (5)
H14	0.0856	0.7812	0.2726	0.024*
C15	0.2381 (3)	0.92511 (18)	0.33890 (15)	0.0212 (5)
H15	0.1514	0.9387	0.3899	0.025*
C16	0.4000 (3)	0.99216 (18)	0.33016 (15)	0.0186 (5)
C17	0.5266 (3)	0.96472 (18)	0.25107 (15)	0.0188 (5)
H17	0.6460	1.0151	0.2481	0.023*
C18	0.4885 (3)	0.87244 (18)	0.18052 (15)	0.0171 (5)
H18	0.5767	0.8588	0.1302	0.021*
C19	0.1690 (4)	0.3024 (2)	0.54959 (18)	0.0327 (6)
H19A	0.0452	0.3391	0.5725	0.049*
H19B	0.2282	0.3589	0.5045	0.049*
H19C	0.2786	0.2830	0.6111	0.049*

	U11	U22	U33	U12	U13	U23
O1	0.0309 (9)	0.0222 (9)	0.0363 (9)	−0.0127 (7)	−0.0028 (7)	0.0079 (7)
O2	0.0336 (9)	0.0277 (9)	0.0282 (9)	−0.0155 (7)	0.0057 (7)	−0.0146 (7)
O3	0.0422 (11)	0.0542 (12)	0.0436 (11)	−0.0301 (9)	0.0073 (8)	−0.0248 (9)
C1	0.0167 (10)	0.0204 (11)	0.0205 (11)	−0.0082 (8)	0.0039 (8)	−0.0053 (8)
C2	0.0215 (11)	0.0245 (12)	0.0170 (10)	−0.0090 (9)	0.0039 (9)	−0.0021 (8)
C3	0.0229 (11)	0.0257 (12)	0.0214 (11)	−0.0088 (9)	−0.0004 (9)	0.0027 (9)
C4	0.0142 (10)	0.0233 (12)	0.0266 (12)	−0.0064 (9)	0.0000 (9)	0.0022 (9)
C5	0.0179 (11)	0.0201 (11)	0.0213 (11)	−0.0076 (8)	0.0023 (9)	−0.0008 (8)
C6	0.0139 (10)	0.0164 (11)	0.0185 (11)	−0.0077 (8)	0.0019 (8)	−0.0020 (8)
C7	0.0183 (10)	0.0164 (11)	0.0157 (10)	−0.0083 (8)	0.0035 (8)	−0.0048 (8)
C8	0.0180 (11)	0.0214 (12)	0.0228 (11)	−0.0100 (9)	0.0005 (9)	−0.0016 (9)
C9	0.0196 (11)	0.0212 (12)	0.0263 (12)	−0.0115 (9)	0.0010 (9)	−0.0004 (9)
C10	0.0247 (11)	0.0173 (11)	0.0177 (10)	−0.0077 (9)	−0.0004 (9)	−0.0009 (8)
C11	0.0154 (10)	0.0219 (11)	0.0232 (11)	−0.0081 (9)	0.0005 (9)	−0.0014 (9)
C12	0.0190 (11)	0.0191 (11)	0.0219 (11)	−0.0119 (9)	0.0020 (9)	−0.0042 (8)
C13	0.0159 (10)	0.0165 (11)	0.0149 (10)	−0.0056 (8)	0.0000 (8)	0.0012 (8)
C14	0.0177 (10)	0.0200 (11)	0.0229 (11)	−0.0109 (9)	0.0049 (8)	0.0000 (8)
C15	0.0236 (11)	0.0226 (12)	0.0193 (11)	−0.0103 (9)	0.0091 (9)	−0.0022 (9)
C16	0.0229 (11)	0.0159 (11)	0.0150 (10)	−0.0068 (9)	−0.0011 (8)	−0.0008 (8)
C17	0.0178 (10)	0.0182 (11)	0.0197 (11)	−0.0104 (9)	0.0017 (9)	0.0023 (8)
C18	0.0165 (10)	0.0186 (11)	0.0163 (10)	−0.0069 (8)	0.0033 (8)	−0.0009 (8)
C19	0.0352 (13)	0.0298 (14)	0.0313 (13)	−0.0126 (11)	0.0018 (11)	−0.0088 (10)

O1—C10	1.499 (2)	C7—C8	1.271 (3)
O1—H1	0.8200	C7—C12	1.462 (3)
O2—C16	1.335 (2)	C8—C9	1.513 (3)
O2—H2	0.8200	C8—H8	0.9300
O3—C19	1.341 (3)	C9—C10	1.446 (3)
O3—H3	0.8200	C9—H9	0.9300
C1—C6	1.560 (3)	C10—C11	1.262 (3)
C1—C2	1.647 (3)	C11—C12	1.511 (3)
C1—H1A	0.9700	C11—H11	0.9300
C1—H1B	0.9700	C12—H12	0.9300
C2—C3	1.562 (3)	C13—C18	1.277 (3)
C2—H2A	0.9700	C13—C14	1.431 (3)
C2—H2B	0.9700	C14—C15	1.341 (3)
C3—C4	1.537 (3)	C14—H14	0.9300
C3—H3A	0.9700	C15—C16	1.266 (3)
C3—H3B	0.9700	C15—H15	0.9300
C4—C5	1.653 (3)	C16—C17	1.421 (3)
C4—H4A	0.9700	C17—C18	1.338 (3)
C4—H4B	0.9700	C17—H17	0.9300
C5—C6	1.586 (3)	C18—H18	0.9300
C5—H5A	0.9700	C19—H19A	0.9600
C5—H5B	0.9700	C19—H19B	0.9600
C6—C13	1.493 (3)	C19—H19C	0.9600
C6—C7	1.666 (3)
C10—O1—H1	109.5	C12—C7—C6	128.71 (15)
C16—O2—H2	109.5	C7—C8—C9	119.95 (19)
C19—O3—H3	109.5	C7—C8—H8	120.0
C6—C1—C2	107.79 (16)	C9—C8—H8	120.0
C6—C1—H1A	110.1	C10—C9—C8	129.39 (16)
C2—C1—H1A	110.1	C10—C9—H9	115.3
C6—C1—H1B	110.1	C8—C9—H9	115.3
C2—C1—H1B	110.1	C11—C10—C9	112.22 (19)
H1A—C1—H1B	108.5	C11—C10—O1	117.78 (18)
C3—C2—C1	120.64 (15)	C9—C10—O1	129.99 (16)
C3—C2—H2A	107.2	C10—C11—C12	117.69 (19)
C1—C2—H2A	107.2	C10—C11—H11	121.2
C3—C2—H2B	107.2	C12—C11—H11	121.2
C1—C2—H2B	107.2	C7—C12—C11	131.45 (16)
H2A—C2—H2B	106.8	C7—C12—H12	114.3
C4—C3—C2	111.17 (16)	C11—C12—H12	114.3
C4—C3—H3A	109.4	C18—C13—C14	116.89 (18)
C2—C3—H3A	109.4	C18—C13—C6	117.07 (18)
C4—C3—H3B	109.4	C14—C13—C6	125.86 (15)
C2—C3—H3B	109.4	C15—C14—C13	127.54 (17)
H3A—C3—H3B	108.0	C15—C14—H14	116.2
C3—C4—C5	104.04 (16)	C13—C14—H14	116.2
C3—C4—H4A	110.9	C16—C15—C14	114.0 (2)
C5—C4—H4A	110.9	C16—C15—H15	123.0
C3—C4—H4B	110.9	C14—C15—H15	123.0
C5—C4—H4B	110.9	C15—C16—O2	114.96 (19)
H4A—C4—H4B	109.0	C15—C16—C17	119.83 (18)
C6—C5—C4	122.27 (14)	O2—C16—C17	125.21 (16)
C6—C5—H5A	106.8	C18—C17—C16	125.45 (17)
C4—C5—H5A	106.8	C18—C17—H17	117.3
C6—C5—H5B	106.8	C16—C17—H17	117.3
C4—C5—H5B	106.8	C13—C18—C17	116.28 (19)
H5A—C5—H5B	106.6	C13—C18—H18	121.9
C13—C6—C1	118.62 (15)	C17—C18—H18	121.9
C13—C6—C5	100.64 (16)	O3—C19—H19A	109.5
C1—C6—C5	106.23 (15)	O3—C19—H19B	109.5
C13—C6—C7	108.39 (14)	H19A—C19—H19B	109.5
C1—C6—C7	102.45 (15)	O3—C19—H19C	109.5
C5—C6—C7	121.61 (14)	H19A—C19—H19C	109.5
C8—C7—C12	109.31 (19)	H19B—C19—H19C	109.5
C8—C7—C6	121.98 (18)
C6—C1—C2—C3	−53.3 (2)	C9—C10—C11—C12	0.5 (3)
C1—C2—C3—C4	54.9 (2)	O1—C10—C11—C12	179.62 (15)
C2—C3—C4—C5	−48.21 (19)	C8—C7—C12—C11	0.3 (3)
C3—C4—C5—C6	57.8 (2)	C6—C7—C12—C11	179.37 (17)
C2—C1—C6—C13	−64.5 (2)	C10—C11—C12—C7	−0.7 (3)
C2—C1—C6—C5	47.66 (18)	C1—C6—C13—C18	−17.5 (3)
C2—C1—C6—C7	176.22 (12)	C5—C6—C13—C18	−132.79 (19)
C4—C5—C6—C13	65.4 (2)	C7—C6—C13—C18	98.6 (2)
C4—C5—C6—C1	−58.8 (2)	C1—C6—C13—C14	167.53 (18)
C4—C5—C6—C7	−175.10 (15)	C5—C6—C13—C14	52.3 (2)
C13—C6—C7—C8	114.6 (2)	C7—C6—C13—C14	−76.4 (2)
C1—C6—C7—C8	−119.2 (2)	C18—C13—C14—C15	1.6 (3)
C5—C6—C7—C8	−1.0 (3)	C6—C13—C14—C15	176.5 (2)
C13—C6—C7—C12	−64.4 (2)	C13—C14—C15—C16	−0.5 (3)
C1—C6—C7—C12	61.8 (2)	C14—C15—C16—O2	179.16 (18)
C5—C6—C7—C12	179.96 (18)	C14—C15—C16—C17	−0.8 (3)
C12—C7—C8—C9	0.2 (3)	C15—C16—C17—C18	1.3 (3)
C6—C7—C8—C9	−179.03 (15)	O2—C16—C17—C18	−178.71 (19)
C7—C8—C9—C10	−0.2 (3)	C14—C13—C18—C17	−1.1 (3)
C8—C9—C10—C11	−0.2 (3)	C6—C13—C18—C17	−176.46 (17)
C8—C9—C10—O1	−179.14 (17)	C16—C17—C18—C13	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.60	2.415 (2)	173
O2—H2···O3ii	0.82	2.08	2.860 (3)	159
O3—H3···O1iii	0.82	1.96	2.767 (2)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.60	2.415 (2)	173
O2—H2⋯O3ii	0.82	2.08	2.860 (3)	159
O3—H3⋯O1iii	0.82	1.96	2.767 (2)	166

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