trans-2-(2-Hydroxy­phenyl)­cyclo­hexanol

Chinnakali, K.; Ravishankar, T.; Sriraghavan, K.; Razak, I.A.; Fun, H.-K.; Chantrapromma, S.; Ramakrishnan, V.T.

doi:10.1107/S160053680101056X

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trans-2-(2-Hydroxyphenyl)cyclohexanol

K. Chinnakali, T. Ravishankar, K. Sriraghavan, I. A. Razak, H.-K. Fun, S. Chantrapromma and V. T. Ramakrishnan

The crystal structure of the title compound, C₁₂H₁₆O₂, contains two crystallographically independent molecules in the asymmetric unit. The cyclohexane rings of these two molecules adopt chair conformations with the hydroxyl groups and benzene rings equatorially attached. The crystal structure is stabilized by O—H

O hydrogen bonds and weak C—H

π interactions involving the phenyl rings.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680101056X/cf6070sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680101056X/cf6070Isup2.hkl Contains datablock I

CCDC reference: 170789

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.078
wR factor = 0.223
Data-to-parameter ratio = 13.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_716  Alert C H...A   Unknown or Inconsistent Label ........       \P(PB)
                           H9B    \P(PB)

PLAT_716  Alert C H...A   Unknown or Inconsistent Label ........       \P(PA)
                           H9D    \P(PA)

PLAT_716  Alert C H...A   Unknown or Inconsistent Label ........       \P(PB)
                           H11B   \P(PB)

PLAT_716  Alert C H...A   Unknown or Inconsistent Label ........       \P(PA)
                           H11C   \P(PA)

PLAT_717  Alert C D...A   Unknown or Inconsistent Label ........       \P(PB)
                           C9A    \P(PB)

PLAT_717  Alert C D...A   Unknown or Inconsistent Label ........       \P(PA)
                           C9B    \P(PA)

PLAT_717  Alert C D...A   Unknown or Inconsistent Label ........       \P(PB)
                           C11A   \P(PB)

PLAT_717  Alert C D...A   Unknown or Inconsistent Label ........       \P(PA)
                           C11B   \P(PA)

PLAT_718  Alert C D-H..A  Unknown or Inconsistent label ........       \P(PB)
                           C9A    H9B    \P(PB)

PLAT_718  Alert C D-H..A  Unknown or Inconsistent label ........       \P(PA)
                           C9B    H9D    \P(PA)

PLAT_718  Alert C D-H..A  Unknown or Inconsistent label ........       \P(PB)
                           C11A   H11B   \P(PB)

PLAT_718  Alert C D-H..A  Unknown or Inconsistent label ........       \P(PA)
                           C11B   H11C   \P(PA)


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 12 Alert Level C = Please check

Comment top

Cyclohexanol and its derivatives have proved to be important tools in both biochemical and physiological studies of the cholimergin nerve terminal (Rogers et al., 1989). Also, many of the cyclohexanol derivatives exhibit good receptor properties against the inhibitor of acetylcholine storage by nerve terminal synaptic vesicles (Marshall & Parsons, 1987). The crystal structure determination of the title compound, (I), one of the above derivatives, was performed in order to elucidate its molecular conformation.

The asymmetric unit of (I) contains two crystallographically independent molecules linked by an O1B—H1C···O2A hydrogen bond, with their centroid at (0.252, 1/4, 0.497). The corresponding bond lengths and angles of these two molecules agree with each other and show normal values. The cyclohexane ring in both molecules adopts the chair conformation and the hydroxyl and phenyl groups are equatorially attached. An O—H···O intramolecular hydrogen bond is observed in one of the two molecules in the asymmetric unit (Table 1). In the solid state, the two independent molecules are alternately linked by O—H···O hydrogen bonds to form an infinite one-dimensional chain along the a direction. The crystal structure is further stabilized by a number of weak C—H···π interactions involving the phenyl rings of molecule A (πPA = centroid of C1A—C6A) and molecule B (πPB = centroid of C1B—C6B).

Experimental top

To a stirred suspension of magnesium turnings (0.75 g-atom) in dry THF (25 ml) under a nitrogen atmosphere was added dropwise a solution of 2-bromoanisole (3.8 ml, 0.03 M) in dry THF (15 ml). After the addition was complete, the solution was cooled to 263 K (using an ice–salt mixture), and cuprous iodide (0.29 g, 1.5 mmol) was added. The resulting mixture was then stirred for a further 15 min, after which time cyclohexane oxide (2 ml, 0.02 M) in dry THF (10 ml) was added dropwise. After completion of the reaction, it was quenched with a saturated solution of ammonium sulfate (50 ml). The reaction mixture was then extracted with ethyl acetate and the organic layer was washed with water, then dried over anhydrous MgSO₄. After removal of the solvent, the residue was chromatographed over silica gel to afford trans-2-(2-methoxyphenyl)cyclohexanol (4.1 g, 98%) as a viscous liquid in 98% yield. It was then further demethylated with chlorotrimethylsilane (2.17 g, 0.02 M) and sodium iodide (3 g, 0.02 M) using dry acetonitrile as solvent, affording the title compound as a crystalline solid (m.p. 367–369 K).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 1990).

Figures top

Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.

trans-2-(2-hydroxyphenyl)-cyclohexanol top

Crystal data top

C₁₂H₁₆O₂	Z = 4
M_r = 192.25	F(000) = 416
Triclinic, P1	D_x = 1.224 Mg m⁻³
a = 9.0290 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.0804 (8) Å	Cell parameters from 2614 reflections
c = 12.1751 (10) Å	θ = 1.8–28.4°
α = 72.031 (2)°	µ = 0.08 mm⁻¹
β = 81.913 (2)°	T = 293 K
γ = 89.545 (2)°	Plate, colourless
V = 1042.9 (1) Å³	0.48 × 0.40 × 0.14 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	1965 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
Detector resolution: 8.33 pixels mm^-1	h = −10→10
ω scans	k = −11→11
5444 measured reflections	l = 0→14
3503 independent reflections

Refinement top

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.121P)²] where P = (F_o² + 2F_c²)/3
3503 reflections	(Δ/σ)_max < 0.001
257 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₂H₁₆O₂	γ = 89.545 (2)°
M_r = 192.25	V = 1042.9 (1) Å³
Triclinic, P1	Z = 4
a = 9.0290 (7) Å	Mo Kα radiation
b = 10.0804 (8) Å	µ = 0.08 mm⁻¹
c = 12.1751 (10) Å	T = 293 K
α = 72.031 (2)°	0.48 × 0.40 × 0.14 mm
β = 81.913 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1965 reflections with I > 2σ(I)
5444 measured reflections	R_int = 0.046
3503 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.223	H-atom parameters constrained
S = 0.96	Δρ_max = 0.29 e Å⁻³
3503 reflections	Δρ_min = −0.32 e Å⁻³
257 parameters

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.

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.

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

	x	y	z	U_iso*/U_eq
O1A	0.6366 (3)	0.2862 (3)	0.4524 (2)	0.0573 (7)
H1A	0.6805	0.3054	0.5005	0.086*
O2A	0.3727 (3)	0.1731 (3)	0.4149 (2)	0.0626 (8)
H2A	0.4441	0.1967	0.4403	0.094*
C1A	0.6423 (4)	0.5366 (4)	0.3718 (3)	0.0532 (10)
H1B	0.6646	0.5461	0.4413	0.064*
C2A	0.6255 (4)	0.6534 (4)	0.2800 (4)	0.0620 (11)
H2B	0.6345	0.7420	0.2874	0.074*
C3A	0.5957 (4)	0.6374 (4)	0.1780 (4)	0.0638 (11)
H3A	0.5866	0.7161	0.1151	0.077*
C4A	0.5786 (4)	0.5064 (4)	0.1666 (3)	0.0538 (10)
H4A	0.5570	0.4986	0.0963	0.065*
C5A	0.5929 (3)	0.3863 (3)	0.2580 (3)	0.0402 (8)
C6A	0.6258 (4)	0.4048 (4)	0.3610 (3)	0.0431 (9)
C7A	0.5765 (3)	0.2407 (4)	0.2488 (3)	0.0412 (8)
H7A	0.6449	0.1824	0.2974	0.049*
C8A	0.6216 (4)	0.2325 (4)	0.1255 (3)	0.0534 (10)
H8A	0.5559	0.2891	0.0746	0.064*
H8B	0.7229	0.2708	0.0966	0.064*
C9A	0.6137 (5)	0.0843 (4)	0.1210 (4)	0.0644 (11)
H9A	0.6397	0.0842	0.0409	0.077*
H9B	0.6853	0.0290	0.1665	0.077*
C10A	0.4583 (4)	0.0204 (4)	0.1686 (3)	0.0616 (11)
H10B	0.4565	−0.0761	0.1693	0.074*
H10A	0.3884	0.0700	0.1181	0.074*
C11A	0.4096 (4)	0.0265 (4)	0.2913 (3)	0.0558 (10)
H11B	0.3075	−0.0104	0.3178	0.067*
H11A	0.4730	−0.0316	0.3434	0.067*
C12A	0.4187 (4)	0.1738 (4)	0.2967 (3)	0.0446 (9)
H12A	0.3485	0.2293	0.2480	0.054*
O1B	0.1221 (3)	0.2119 (3)	0.5432 (2)	0.0573 (7)
H1C	0.1905	0.1935	0.4990	0.086*
O2B	−0.1611 (3)	0.3230 (3)	0.5799 (2)	0.0603 (8)
H2C	−0.0748	0.3256	0.5473	0.090*
C1B	0.0957 (4)	−0.0388 (4)	0.6229 (3)	0.0520 (10)
H1D	0.1458	−0.0494	0.5541	0.062*
C2B	0.0419 (4)	−0.1540 (4)	0.7140 (3)	0.0559 (10)
H2D	0.0556	−0.2425	0.7064	0.067*
C3B	−0.0315 (4)	−0.1404 (4)	0.8156 (3)	0.0526 (10)
H3B	−0.0687	−0.2188	0.8769	0.063*
C4B	−0.0499 (4)	−0.0073 (4)	0.8258 (3)	0.0440 (9)
H4B	−0.0984	0.0017	0.8957	0.053*
C5B	0.0009 (3)	0.1113 (3)	0.7366 (3)	0.0383 (8)
C6B	0.0753 (4)	0.0941 (4)	0.6331 (3)	0.0434 (8)
C7B	−0.0191 (3)	0.2574 (3)	0.7458 (3)	0.0381 (8)
H7B	0.0673	0.3146	0.6969	0.046*
C8B	−0.0202 (4)	0.2668 (4)	0.8681 (3)	0.0464 (9)
H8C	−0.1041	0.2106	0.9194	0.056*
H8D	0.0709	0.2284	0.8969	0.056*
C9B	−0.0317 (4)	0.4152 (4)	0.8729 (3)	0.0568 (10)
H9C	−0.0371	0.4149	0.9531	0.068*
H9D	0.0569	0.4699	0.8281	0.068*
C10B	−0.1697 (4)	0.4809 (4)	0.8239 (3)	0.0578 (10)
H10D	−0.2586	0.4327	0.8742	0.069*
H10C	−0.1714	0.5777	0.8223	0.069*
C11B	−0.1713 (4)	0.4735 (4)	0.7023 (3)	0.0584 (11)
H11D	−0.0882	0.5304	0.6504	0.070*
H11C	−0.2632	0.5117	0.6752	0.070*
C12B	−0.1597 (4)	0.3248 (4)	0.6967 (3)	0.0442 (9)
H12B	−0.2478	0.2703	0.7457	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0737 (18)	0.0551 (16)	0.0487 (15)	0.0099 (13)	−0.0267 (13)	−0.0167 (12)
O2A	0.0514 (16)	0.084 (2)	0.0534 (16)	−0.0049 (15)	0.0091 (13)	−0.0306 (14)
C1A	0.047 (2)	0.061 (3)	0.059 (2)	0.0105 (18)	−0.0151 (18)	−0.026 (2)
C2A	0.057 (2)	0.047 (2)	0.086 (3)	0.0159 (19)	−0.023 (2)	−0.022 (2)
C3A	0.064 (3)	0.050 (3)	0.072 (3)	0.0168 (19)	−0.025 (2)	−0.005 (2)
C4A	0.053 (2)	0.051 (2)	0.057 (2)	0.0111 (18)	−0.0214 (18)	−0.0098 (19)
C5A	0.0322 (17)	0.047 (2)	0.0402 (18)	0.0092 (15)	−0.0073 (14)	−0.0104 (16)
C6A	0.0369 (18)	0.046 (2)	0.046 (2)	0.0117 (15)	−0.0107 (15)	−0.0120 (17)
C7A	0.0308 (17)	0.049 (2)	0.0434 (19)	0.0112 (15)	−0.0102 (14)	−0.0114 (16)
C8A	0.048 (2)	0.063 (3)	0.052 (2)	0.0042 (18)	−0.0056 (17)	−0.0218 (19)
C9A	0.063 (3)	0.073 (3)	0.064 (3)	0.013 (2)	−0.002 (2)	−0.034 (2)
C10A	0.064 (3)	0.061 (3)	0.069 (3)	0.009 (2)	−0.019 (2)	−0.030 (2)
C11A	0.052 (2)	0.048 (2)	0.065 (2)	0.0012 (17)	−0.0116 (19)	−0.0112 (19)
C12A	0.0367 (18)	0.051 (2)	0.044 (2)	0.0091 (15)	−0.0070 (15)	−0.0114 (16)
O1B	0.0577 (17)	0.0538 (16)	0.0537 (16)	0.0122 (12)	0.0091 (12)	−0.0147 (13)
O2B	0.0558 (16)	0.0805 (19)	0.0523 (15)	0.0283 (15)	−0.0255 (12)	−0.0247 (14)
C1B	0.046 (2)	0.058 (3)	0.055 (2)	0.0201 (18)	−0.0082 (17)	−0.023 (2)
C2B	0.054 (2)	0.044 (2)	0.073 (3)	0.0175 (18)	−0.017 (2)	−0.019 (2)
C3B	0.053 (2)	0.043 (2)	0.057 (2)	0.0055 (17)	−0.0133 (18)	−0.0063 (18)
C4B	0.0410 (19)	0.050 (2)	0.0408 (19)	0.0098 (16)	−0.0071 (15)	−0.0130 (17)
C5B	0.0267 (16)	0.048 (2)	0.0402 (18)	0.0106 (14)	−0.0117 (14)	−0.0115 (16)
C6B	0.0397 (19)	0.048 (2)	0.043 (2)	0.0134 (16)	−0.0076 (15)	−0.0137 (17)
C7B	0.0312 (16)	0.043 (2)	0.0385 (18)	0.0096 (14)	−0.0048 (14)	−0.0104 (15)
C8B	0.049 (2)	0.050 (2)	0.045 (2)	0.0102 (16)	−0.0159 (16)	−0.0175 (17)
C9B	0.065 (2)	0.054 (2)	0.059 (2)	0.0090 (19)	−0.0157 (19)	−0.0253 (19)
C10B	0.059 (2)	0.050 (2)	0.068 (3)	0.0161 (18)	−0.008 (2)	−0.0248 (19)
C11B	0.056 (2)	0.051 (2)	0.065 (3)	0.0211 (18)	−0.0133 (19)	−0.0114 (19)
C12B	0.0385 (18)	0.049 (2)	0.043 (2)	0.0126 (15)	−0.0100 (15)	−0.0092 (16)

Geometric parameters (Å, º) top

O1A—C6A	1.374 (4)	O1B—C6B	1.365 (4)
O1A—H1A	0.820	O1B—H1C	0.820
O2A—C12A	1.439 (4)	O2B—C12B	1.429 (4)
O2A—H2A	0.820	O2B—H2C	0.820
C1A—C2A	1.375 (5)	C1B—C2B	1.370 (5)
C1A—C6A	1.386 (5)	C1B—C6B	1.392 (5)
C1A—H1B	0.930	C1B—H1D	0.930
C2A—C3A	1.363 (5)	C2B—C3B	1.364 (5)
C2A—H2B	0.930	C2B—H2D	0.930
C3A—C4A	1.382 (5)	C3B—C4B	1.392 (5)
C3A—H3A	0.930	C3B—H3B	0.930
C4A—C5A	1.389 (5)	C4B—C5B	1.374 (4)
C4A—H4A	0.930	C4B—H4B	0.930
C5A—C6A	1.395 (5)	C5B—C6B	1.401 (4)
C5A—C7A	1.516 (5)	C5B—C7B	1.519 (5)
C7A—C8A	1.527 (4)	C7B—C8B	1.520 (4)
C7A—C12A	1.537 (5)	C7B—C12B	1.543 (4)
C7A—H7A	0.980	C7B—H7B	0.980
C8A—C9A	1.515 (6)	C8B—C9B	1.516 (5)
C8A—H8A	0.970	C8B—H8C	0.970
C8A—H8B	0.970	C8B—H8D	0.970
C9A—C10A	1.509 (6)	C9B—C10B	1.516 (5)
C9A—H9A	0.970	C9B—H9C	0.970
C9A—H9B	0.970	C9B—H9D	0.970
C10A—C11A	1.516 (5)	C10B—C11B	1.507 (5)
C10A—H10B	0.970	C10B—H10D	0.970
C10A—H10A	0.970	C10B—H10C	0.970
C11A—C12A	1.509 (5)	C11B—C12B	1.523 (5)
C11A—H11B	0.970	C11B—H11D	0.970
C11A—H11A	0.970	C11B—H11C	0.970
C12A—H12A	0.980	C12B—H12B	0.980

C6A—O1A—H1A	109.5	C6B—O1B—H1C	109.5
C12A—O2A—H2A	109.5	C12B—O2B—H2C	109.5
C2A—C1A—C6A	120.2 (4)	C2B—C1B—C6B	120.0 (3)
C2A—C1A—H1B	119.9	C2B—C1B—H1D	120.0
C6A—C1A—H1B	119.9	C6B—C1B—H1D	120.0
C3A—C2A—C1A	119.0 (4)	C3B—C2B—C1B	120.8 (4)
C3A—C2A—H2B	120.5	C3B—C2B—H2D	119.6
C1A—C2A—H2B	120.5	C1B—C2B—H2D	119.6
C2A—C3A—C4A	121.2 (4)	C2B—C3B—C4B	118.9 (3)
C2A—C3A—H3A	119.4	C2B—C3B—H3B	120.5
C4A—C3A—H3A	119.4	C4B—C3B—H3B	120.5
C3A—C4A—C5A	121.3 (4)	C5B—C4B—C3B	122.4 (3)
C3A—C4A—H4A	119.4	C5B—C4B—H4B	118.8
C5A—C4A—H4A	119.4	C3B—C4B—H4B	118.8
C4A—C5A—C6A	116.7 (3)	C4B—C5B—C6B	117.4 (3)
C4A—C5A—C7A	123.0 (3)	C4B—C5B—C7B	123.2 (3)
C6A—C5A—C7A	120.3 (3)	C6B—C5B—C7B	119.4 (3)
O1A—C6A—C1A	121.5 (3)	O1B—C6B—C1B	122.1 (3)
O1A—C6A—C5A	116.8 (3)	O1B—C6B—C5B	117.5 (3)
C1A—C6A—C5A	121.6 (3)	C1B—C6B—C5B	120.5 (3)
C5A—C7A—C8A	113.7 (3)	C5B—C7B—C8B	114.3 (3)
C5A—C7A—C12A	113.4 (2)	C5B—C7B—C12B	112.4 (3)
C8A—C7A—C12A	109.1 (3)	C8B—C7B—C12B	109.6 (2)
C5A—C7A—H7A	106.7	C5B—C7B—H7B	106.7
C8A—C7A—H7A	106.7	C8B—C7B—H7B	106.7
C12A—C7A—H7A	106.7	C12B—C7B—H7B	106.7
C9A—C8A—C7A	112.3 (3)	C9B—C8B—C7B	112.9 (3)
C9A—C8A—H8A	109.1	C9B—C8B—H8C	109.0
C7A—C8A—H8A	109.1	C7B—C8B—H8C	109.0
C9A—C8A—H8B	109.1	C9B—C8B—H8D	109.0
C7A—C8A—H8B	109.1	C7B—C8B—H8D	109.0
H8A—C8A—H8B	107.9	H8C—C8B—H8D	107.8
C10A—C9A—C8A	110.4 (3)	C10B—C9B—C8B	110.5 (3)
C10A—C9A—H9A	109.6	C10B—C9B—H9C	109.5
C8A—C9A—H9A	109.6	C8B—C9B—H9C	109.5
C10A—C9A—H9B	109.6	C10B—C9B—H9D	109.5
C8A—C9A—H9B	109.6	C8B—C9B—H9D	109.5
H9A—C9A—H9B	108.1	H9C—C9B—H9D	108.1
C9A—C10A—C11A	111.2 (3)	C11B—C10B—C9B	111.2 (3)
C9A—C10A—H10B	109.4	C11B—C10B—H10D	109.4
C11A—C10A—H10B	109.4	C9B—C10B—H10D	109.4
C9A—C10A—H10A	109.4	C11B—C10B—H10C	109.4
C11A—C10A—H10A	109.4	C9B—C10B—H10C	109.4
H10B—C10A—H10A	108.0	H10D—C10B—H10C	108.0
C12A—C11A—C10A	111.7 (3)	C10B—C11B—C12B	112.4 (3)
C12A—C11A—H11B	109.3	C10B—C11B—H11D	109.1
C10A—C11A—H11B	109.3	C12B—C11B—H11D	109.1
C12A—C11A—H11A	109.3	C10B—C11B—H11C	109.1
C10A—C11A—H11A	109.3	C12B—C11B—H11C	109.1
H11B—C11A—H11A	107.9	H11D—C11B—H11C	107.8
O2A—C12A—C11A	109.3 (3)	O2B—C12B—C11B	110.4 (3)
O2A—C12A—C7A	111.6 (3)	O2B—C12B—C7B	111.6 (3)
C11A—C12A—C7A	111.5 (3)	C11B—C12B—C7B	110.7 (3)
O2A—C12A—H12A	108.1	O2B—C12B—H12B	108.0
C11A—C12A—H12A	108.1	C11B—C12B—H12B	108.0
C7A—C12A—H12A	108.1	C7B—C12B—H12B	108.0

C6A—C1A—C2A—C3A	−1.3 (6)	C6B—C1B—C2B—C3B	−0.2 (5)
C1A—C2A—C3A—C4A	1.5 (6)	C1B—C2B—C3B—C4B	−0.6 (5)
C2A—C3A—C4A—C5A	−0.8 (6)	C2B—C3B—C4B—C5B	1.2 (5)
C3A—C4A—C5A—C6A	−0.2 (5)	C3B—C4B—C5B—C6B	−0.9 (5)
C3A—C4A—C5A—C7A	−179.4 (3)	C3B—C4B—C5B—C7B	179.5 (3)
C2A—C1A—C6A—O1A	−177.7 (3)	C2B—C1B—C6B—O1B	−177.5 (3)
C2A—C1A—C6A—C5A	0.3 (5)	C2B—C1B—C6B—C5B	0.5 (5)
C4A—C5A—C6A—O1A	178.5 (3)	C4B—C5B—C6B—O1B	178.2 (3)
C7A—C5A—C6A—O1A	−2.3 (4)	C7B—C5B—C6B—O1B	−2.3 (4)
C4A—C5A—C6A—C1A	0.5 (5)	C4B—C5B—C6B—C1B	0.1 (5)
C7A—C5A—C6A—C1A	179.7 (3)	C7B—C5B—C6B—C1B	179.7 (3)
C4A—C5A—C7A—C8A	29.4 (4)	C4B—C5B—C7B—C8B	31.0 (4)
C6A—C5A—C7A—C8A	−149.7 (3)	C6B—C5B—C7B—C8B	−148.5 (3)
C4A—C5A—C7A—C12A	−96.0 (4)	C4B—C5B—C7B—C12B	−94.7 (3)
C6A—C5A—C7A—C12A	84.9 (4)	C6B—C5B—C7B—C12B	85.7 (3)
C5A—C7A—C8A—C9A	176.2 (3)	C5B—C7B—C8B—C9B	176.8 (3)
C12A—C7A—C8A—C9A	−56.2 (4)	C12B—C7B—C8B—C9B	−55.9 (4)
C7A—C8A—C9A—C10A	57.2 (4)	C7B—C8B—C9B—C10B	56.4 (4)
C8A—C9A—C10A—C11A	−55.8 (4)	C8B—C9B—C10B—C11B	−54.9 (4)
C9A—C10A—C11A—C12A	55.8 (4)	C9B—C10B—C11B—C12B	55.8 (4)
C10A—C11A—C12A—O2A	−179.5 (3)	C10B—C11B—C12B—O2B	−179.8 (3)
C10A—C11A—C12A—C7A	−55.7 (4)	C10B—C11B—C12B—C7B	−55.6 (4)
C5A—C7A—C12A—O2A	−54.7 (4)	C5B—C7B—C12B—O2B	−53.8 (4)
C8A—C7A—C12A—O2A	177.5 (3)	C8B—C7B—C12B—O2B	177.9 (3)
C5A—C7A—C12A—C11A	−177.2 (3)	C5B—C7B—C12B—C11B	−177.3 (3)
C8A—C7A—C12A—C11A	55.0 (4)	C8B—C7B—C12B—C11B	54.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2Bⁱ	0.82	1.87	2.655 (4)	159
O1B—H1C···O2A	0.82	1.86	2.661 (4)	167
O2A—H2A···O1A	0.82	2.01	2.803 (4)	163
O2B—H2C···O1B	0.82	2.11	2.817 (4)	144
C7A—H7A···O1A	0.98	2.42	2.781 (4)	101
C7B—H7B···O1B	0.98	2.40	2.779 (4)	103
C9A—H9B···π(PB)ⁱⁱ	0.97	3.11	3.965 (5)	148
C9B—H9D···π(PA)ⁱⁱⁱ	0.97	3.06	3.924 (4)	149
C11A—H11B···π(PB)^iv	0.97	3.09	3.931 (4)	146
C11B—H11C···π(PA)^v	0.97	3.11	3.930 (4)	144

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z+1; (v) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆O₂
M_r	192.25
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.0290 (7), 10.0804 (8), 12.1751 (10)
α, β, γ (°)	72.031 (2), 81.913 (2), 89.545 (2)
V (Å³)	1042.9 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.48 × 0.40 × 0.14

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5444, 3503, 1965
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.223, 0.96
No. of reflections	3503
No. of parameters	257
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.32

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL and PLATON (Spek, 1990).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O2Bⁱ	0.82	1.87	2.655 (4)	159
O1B—H1C···O2A	0.82	1.86	2.661 (4)	167
O2A—H2A···O1A	0.82	2.01	2.803 (4)	163
O2B—H2C···O1B	0.82	2.11	2.817 (4)	144
C9A—H9B···π(PB)ⁱⁱ	0.97	3.11	3.965 (5)	148
C9B—H9D···π(PA)ⁱⁱⁱ	0.97	3.06	3.924 (4)	149
C11A—H11B···π(PB)^iv	0.97	3.09	3.931 (4)	146
C11B—H11C···π(PA)^v	0.97	3.11	3.930 (4)	144

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, −y, −z+1; (v) −x, −y+1, −z+1.

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