2-(Biphenyl-4-yl)propan-2-ol

Modau, E.; Liles, D.C.; Rooyen, P.H. van

doi:10.1107/S1600536812003716

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o580

doi:10.1107/S1600536812003716

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2-(Biphenyl-4-yl)propan-2-ol

Eric Modau,^a David C. Liles ^a and Petrus H. van Rooyen ^a ^*

^aDepartment of Chemistry, University of Pretoria, Private Bag X20, Hatfield 0028, South Africa
^*Correspondence e-mail: phvr@up.ac.za

(Received 23 January 2012; accepted 27 January 2012; online 4 February 2012)

The title compound, C₁₅H₁₆O, crystallizes with two independent molecules in the asymmetric unit. Due to the space-group symmetry, this results in the formation of a tetramer where the four molecules are connected by O—H⋯O hydrogen bonds. The molecules pack parallel to the c axis. Both molecules in the asymmetric unit are nonplanar and the dihedral angles between connected aromatic rings in each molecule are 7.96 (12) and 9.75 (13)°. This contrasts with the gas phase density functional theory (DFT) optimized conformation, where this dihedral angle is 39.33°.

Related literature

For some previous studies of biphenyl derivitives, see: Britton & Gleason (1991 ); Britton & Young (2003 ); Brock (1980 ); Brock & Haller (1980 ); Mohamed et al. (2003 ). For details of GAUSSIAN03, see: Frisch et al. (2003 ).

Experimental

Crystal data

C₁₅H₁₆O
M_r = 212.28
Monoclinic, C 2/c
a = 12.4406 (14) Å
b = 15.5754 (18) Å
c = 25.741 (3) Å
β = 102.332 (2)°
V = 4872.7 (10) Å³
Z = 16
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 295 K
0.46 × 0.36 × 0.08 mm

Data collection

Bruker P4 diffractometer with SMART 1000 CCD area detector
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.931, T_max = 0.994
12927 measured reflections
4590 independent reflections
2859 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.147
S = 1.01
4590 reflections
391 parameters
3 restraints
All H-atom parameters refined
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2	0.90 (1)	1.99 (2)	2.804 (2)	150 (4)
O2—H2A⋯O1	0.90 (1)	2.09 (4)	2.804 (2)	136 (4)
O1—H1B⋯O1ⁱ	0.87 (3)	1.90 (3)	2.767 (3)	174 (4)
O2—H2B⋯O2ⁱ	0.89 (1)	2.03 (1)	2.926 (3)	177 (4)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ), Mercury (Macrae et al., 2008 ) and POV-RAY (Cason, 2004 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812003716/zq2152sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003716/zq2152Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003716/zq2152Isup3.cml

checkCIF report

Comment top

The studies of the series of biphenyl derivatives have attracted considerable attention for some time now. This included the para-monosubstituted derivatives 4-bromobiphenyl (Brock, 1980) and 4-hydroxylbiphenyl (Brock & Haller, 1980), as well as some para-disubstituted derivatives such as 4,4'-dibromobiphenyl (Mohamed et al., 2003), 4,4'-iodocyanobiphenyl (Britton & Gleason, 1991) and 4,4'-dicyanobiphenyl (Britton & Young, 2003). Particular interest has been shown in their packing motifs as well as the inter-ring dihedral angles which are found to be approximately 40° in the solid state in the majority of structures. The structure of the corresponding 2-(4-biphenyl)-2-propanol compound, was undertaken as part of the investigation into the conformational properties of para monosubstituted and para disubstituted biphenyls. Of significance is that this compound crystallizes in a significantly more planar conformation than what is expected, although it is still non-planar.

2-(4-biphenyl)-2-propanol crystallizes with two independent molecules in the asymmetric unit. The presence of a twofold rotational axis results in the formation of a hydrogen bonded tetramer. The four H atoms of the hydroxyl groups occupy both sets of possible hydrogen positions, illustrated by the two possible bonding schemes (H···O_A—H···O_B—H) and (H—O_A···H—O_B···H). Both sets of H atom positions were refined with occupancies of 0.5. The two molecules in the asymmetric unit have similar geometrical parameters. The molecules are non-planar: the two aromatic rings in each molecule are slightly twisted around C—C inter ring bond by 7.96 (3)° and 9.75 (3)°. This contrasts to the gas phase DFT (6–31+G**) optimized conformation where this dihedral angle is 39.33° (GAUSSIAN03, Frisch et al., 2003). The anisotropic displacement ellipsoids and atom labelling for the compound is shown in Fig.1. The lengths of the central C—C bonds connecting the two aromatic rings in each of the two molecules are equal to 1.491 (3) and 1.489 (2) Å. The bond length and bond angle are within the expected values. The H···O distances are 1.99 (2), 2.09 (4), 1.90 (3) and 2.034 (11) Å. The molecules pack parallel to the c axis (Fig. 2). The volume per non H atom in the crystal is 19.03 Å³, in line with that calculated for other biphenyl derivatives structures. This would suggest that the closer packing resulting from the intermolecular hydrogen bonds as well as the more planar biphenyl systems does not significantly change the packing requirements in the crystals.

Related literature top

For some previous studies of biphenyl derivitives, see: Britton & Gleason (1991); Britton & Young (2003); Brock (1980); Brock & Haller (1980); Mohamed et al. (2003). For details of GAUSSIAN03, see: Frisch et al. (2003).

Experimental top

The title compound was obtained from Aldrich Chemical Co. Inc. Crystals were grown from distilled hexane, acetone, benzene, dichloromethane, chloroform, carbon tetrachloride, and acetonitrile in an attempt to search for multiple polymorphs. Several habits were found, viz. prisms, clear plates, and striated plates but all proved to be isostructural. A prism grown from distilled hexane was used for the structure determination.

Geometry optimization for 2-(4-biphenyl)-2-propanol was performed using the program GAUSSIAN03 and applying the B3LYP-functional with the 6-31+G** basis set level (Frisch et al., 2003). This optimized structure displayed no negative vibrational frequencies.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008) and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), Mercury (Macrae et al., 2008) and POV-RAY (Cason, 2004); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Perspective view of the asymmetric unit of the title compound, with the atom numbering. This shows one of the two possible orientations of the hydrogen bonding scheme. Displacement ellipsoids are shown at the 50% probability level.
	Fig. 2. Drawing of the unit cell content of the title compound.

2-(Biphenyl-4-yl)propan-2-ol top

Crystal data top

C₁₅H₁₆O	F(000) = 1824
M_r = 212.28	D_x = 1.157 Mg m⁻³
Monoclinic, C2/c	Melting point: 366.1 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 12.4406 (14) Å	Cell parameters from 4663 reflections
b = 15.5754 (18) Å	θ = 2.4–26.0°
c = 25.741 (3) Å	µ = 0.07 mm⁻¹
β = 102.332 (2)°	T = 295 K
V = 4872.7 (10) Å³	Plate, colourless
Z = 16	0.46 × 0.36 × 0.08 mm

Data collection top

Bruker P4 diffractometer with SMART 1000 CCD area detector	4590 independent reflections
Radiation source: fine-focus sealed tube	2859 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 8.3 pixels mm^-1	θ_max = 26.5°, θ_min = 2.4°
ϕ and ω scans	h = −15→7
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −18→15
T_min = 0.931, T_max = 0.994	l = −31→31
12927 measured 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)] = 0.046	Hydrogen site location: difference Fourier map
wR(F²) = 0.147	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.0639P)² + 1.7634P] where P = (F_o² + 2F_c²)/3
4590 reflections	(Δ/σ)_max = 0.001
391 parameters	Δρ_max = 0.13 e Å⁻³
3 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₅H₁₆O	V = 4872.7 (10) Å³
M_r = 212.28	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 12.4406 (14) Å	µ = 0.07 mm⁻¹
b = 15.5754 (18) Å	T = 295 K
c = 25.741 (3) Å	0.46 × 0.36 × 0.08 mm
β = 102.332 (2)°

Data collection top

Bruker P4 diffractometer with SMART 1000 CCD area detector	4590 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2859 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.994	R_int = 0.029
12927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	3 restraints
wR(F²) = 0.147	All H-atom parameters refined
S = 1.01	Δρ_max = 0.13 e Å⁻³
4590 reflections	Δρ_min = −0.14 e Å⁻³
391 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	Occ. (<1)
C1	0.22391 (12)	0.49260 (10)	0.05345 (6)	0.0485 (4)
C2	0.28952 (16)	0.44401 (13)	0.09272 (7)	0.0646 (5)
H2	0.3512 (17)	0.4133 (13)	0.0851 (7)	0.078*
C3	0.26765 (16)	0.43652 (13)	0.14308 (7)	0.0650 (5)
H3	0.3152 (16)	0.4000 (13)	0.1686 (8)	0.078*
C4	0.17907 (13)	0.47641 (11)	0.15649 (7)	0.0530 (4)
C5	0.11288 (16)	0.52481 (14)	0.11731 (8)	0.0687 (5)
H5	0.0523 (17)	0.5571 (13)	0.1256 (8)	0.082*
C6	0.13494 (16)	0.53305 (13)	0.06735 (8)	0.0654 (5)
H6	0.0899 (16)	0.5687 (13)	0.0427 (8)	0.078*
C7	0.24761 (13)	0.50013 (10)	−0.00067 (6)	0.0510 (4)
C8	0.17499 (17)	0.53907 (14)	−0.04217 (8)	0.0715 (6)
H8	0.1095 (18)	0.5621 (14)	−0.0353 (8)	0.086*
C9	0.1975 (2)	0.54432 (17)	−0.09240 (9)	0.0839 (7)
H9	0.1447 (19)	0.5734 (15)	−0.1189 (9)	0.101*
C10	0.2925 (2)	0.51127 (15)	−0.10229 (8)	0.0790 (6)
H10	0.3063 (18)	0.5144 (14)	−0.1383 (9)	0.095*
C11	0.36620 (19)	0.47263 (16)	−0.06195 (8)	0.0795 (6)
H11	0.4342 (19)	0.4466 (14)	−0.0681 (8)	0.095*
C12	0.34381 (17)	0.46705 (14)	−0.01181 (8)	0.0693 (5)
H12	0.3974 (17)	0.4414 (13)	0.0170 (8)	0.083*
C13	0.15214 (15)	0.46972 (12)	0.21136 (7)	0.0599 (5)
C14	0.2251 (2)	0.40631 (18)	0.24767 (9)	0.0803 (6)
H14A	0.222 (2)	0.3454 (19)	0.2307 (10)	0.120*
H14B	0.199 (2)	0.4014 (17)	0.2819 (11)	0.120*
H14C	0.301 (2)	0.4270 (17)	0.2564 (10)	0.120*
C15	0.1579 (2)	0.55713 (16)	0.23792 (10)	0.0855 (7)
H15A	0.104 (2)	0.6003 (19)	0.2143 (11)	0.128*
H15B	0.236 (2)	0.5802 (18)	0.2442 (11)	0.128*
H15C	0.139 (2)	0.5516 (17)	0.2739 (12)	0.128*
O1	0.03981 (11)	0.44009 (9)	0.20377 (5)	0.0678 (4)
H1A	0.047 (3)	0.3863 (12)	0.1923 (16)	0.081*	0.50
H1B	0.012 (4)	0.443 (2)	0.2319 (15)	0.081*	0.50
C16	0.00267 (14)	0.24680 (11)	−0.00238 (8)	0.0573 (4)
C17	0.07693 (17)	0.27485 (15)	0.04215 (9)	0.0787 (6)
H17	0.1405 (19)	0.3030 (15)	0.0365 (8)	0.094*
C18	0.05831 (18)	0.26437 (15)	0.09270 (9)	0.0805 (7)
H18	0.1060 (19)	0.2895 (15)	0.1211 (9)	0.097*
C19	−0.03521 (14)	0.22565 (11)	0.10169 (8)	0.0608 (5)
C20	−0.11092 (17)	0.19968 (15)	0.05718 (9)	0.0774 (6)
H20	−0.1768 (19)	0.1719 (14)	0.0629 (8)	0.093*
C21	−0.09266 (17)	0.20967 (15)	0.00691 (9)	0.0766 (6)
H21	−0.1457 (18)	0.1882 (14)	−0.0227 (9)	0.092*
C22	0.02432 (14)	0.25405 (11)	−0.05698 (8)	0.0594 (5)
C23	−0.04138 (19)	0.21334 (18)	−0.10009 (10)	0.0887 (7)
H23	−0.100 (2)	0.1765 (16)	−0.0918 (9)	0.106*
C24	−0.0217 (2)	0.2200 (2)	−0.15056 (11)	0.1001 (8)
H24	−0.064 (2)	0.1888 (18)	−0.1788 (11)	0.120*
C25	0.0651 (2)	0.26587 (16)	−0.15981 (11)	0.0867 (7)
H25	0.0803 (19)	0.2704 (15)	−0.1976 (10)	0.104*
C26	0.1323 (2)	0.30524 (17)	−0.11834 (11)	0.0952 (7)
H26	0.195 (2)	0.3407 (17)	−0.1234 (10)	0.114*
C27	0.1118 (2)	0.29994 (15)	−0.06773 (10)	0.0849 (7)
H27	0.1563 (19)	0.3281 (16)	−0.0394 (10)	0.102*
C28	−0.05169 (16)	0.20597 (13)	0.15723 (8)	0.0696 (5)
C29	−0.1704 (2)	0.2169 (2)	0.16242 (13)	0.1090 (10)
H29A	−0.214 (3)	0.168 (2)	0.1416 (13)	0.163*
H29B	−0.173 (3)	0.209 (2)	0.1994 (14)	0.163*
H29C	−0.191 (3)	0.276 (2)	0.1486 (14)	0.163*
C30	−0.0115 (3)	0.11470 (18)	0.17181 (12)	0.1097 (10)
H30A	−0.053 (3)	0.075 (2)	0.1448 (14)	0.165*
H30B	−0.023 (3)	0.103 (2)	0.2069 (14)	0.165*
H30C	0.070 (3)	0.116 (2)	0.1726 (13)	0.165*
O2	0.01619 (14)	0.26127 (10)	0.19536 (6)	0.0871 (5)
H2A	0.000 (4)	0.3133 (16)	0.1811 (19)	0.104*	0.50
H2B	0.007 (5)	0.259 (3)	0.2287 (9)	0.104*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0478 (9)	0.0447 (9)	0.0519 (10)	−0.0059 (7)	0.0082 (7)	−0.0009 (7)
C2	0.0578 (11)	0.0760 (13)	0.0614 (11)	0.0171 (9)	0.0157 (9)	0.0078 (10)
C3	0.0634 (11)	0.0742 (13)	0.0569 (11)	0.0143 (10)	0.0115 (9)	0.0145 (10)
C4	0.0543 (10)	0.0526 (10)	0.0523 (9)	−0.0055 (8)	0.0116 (8)	0.0004 (8)
C5	0.0636 (11)	0.0817 (14)	0.0641 (12)	0.0198 (10)	0.0210 (10)	0.0090 (10)
C6	0.0638 (11)	0.0740 (13)	0.0585 (11)	0.0184 (9)	0.0134 (9)	0.0121 (9)
C7	0.0531 (9)	0.0477 (9)	0.0508 (9)	−0.0077 (7)	0.0080 (7)	−0.0051 (8)
C8	0.0641 (12)	0.0897 (15)	0.0605 (12)	0.0096 (11)	0.0129 (10)	0.0086 (10)
C9	0.0842 (15)	0.1084 (19)	0.0564 (12)	0.0126 (13)	0.0089 (11)	0.0125 (12)
C10	0.0921 (16)	0.0942 (16)	0.0522 (12)	−0.0060 (12)	0.0189 (11)	−0.0031 (11)
C11	0.0799 (14)	0.0985 (17)	0.0646 (13)	0.0091 (12)	0.0253 (11)	−0.0048 (12)
C12	0.0671 (12)	0.0843 (14)	0.0565 (11)	0.0109 (10)	0.0133 (9)	0.0008 (10)
C13	0.0632 (11)	0.0641 (11)	0.0536 (10)	−0.0071 (9)	0.0155 (8)	0.0003 (8)
C14	0.0842 (15)	0.1001 (18)	0.0554 (12)	0.0009 (13)	0.0121 (11)	0.0148 (12)
C15	0.1139 (19)	0.0788 (15)	0.0682 (14)	−0.0162 (13)	0.0292 (14)	−0.0145 (12)
O1	0.0656 (8)	0.0812 (9)	0.0623 (8)	−0.0060 (7)	0.0260 (6)	−0.0004 (7)
C16	0.0517 (10)	0.0466 (10)	0.0703 (12)	−0.0018 (8)	0.0058 (8)	−0.0028 (8)
C17	0.0620 (12)	0.0926 (16)	0.0821 (15)	−0.0288 (11)	0.0170 (11)	−0.0167 (12)
C18	0.0665 (13)	0.0997 (17)	0.0731 (14)	−0.0284 (11)	0.0101 (11)	−0.0239 (12)
C19	0.0587 (10)	0.0523 (10)	0.0711 (12)	−0.0050 (8)	0.0129 (9)	−0.0118 (9)
C20	0.0628 (12)	0.0896 (15)	0.0781 (15)	−0.0270 (11)	0.0113 (11)	−0.0060 (12)
C21	0.0636 (12)	0.0893 (15)	0.0710 (14)	−0.0240 (11)	0.0012 (10)	−0.0047 (11)
C22	0.0541 (10)	0.0458 (10)	0.0749 (13)	0.0044 (8)	0.0063 (9)	0.0015 (9)
C23	0.0703 (14)	0.1149 (19)	0.0760 (15)	−0.0245 (13)	0.0046 (11)	−0.0042 (13)
C24	0.0944 (18)	0.129 (2)	0.0716 (16)	−0.0171 (16)	0.0056 (13)	−0.0087 (15)
C25	0.0967 (17)	0.0844 (16)	0.0806 (16)	0.0126 (13)	0.0224 (14)	0.0113 (13)
C26	0.1011 (18)	0.0903 (17)	0.102 (2)	−0.0217 (14)	0.0382 (16)	0.0034 (15)
C27	0.0867 (15)	0.0809 (15)	0.0872 (17)	−0.0247 (12)	0.0190 (13)	−0.0080 (12)
C28	0.0766 (12)	0.0622 (12)	0.0710 (13)	−0.0150 (10)	0.0182 (10)	−0.0169 (10)
C29	0.0908 (18)	0.147 (3)	0.098 (2)	−0.0350 (18)	0.0402 (16)	−0.0268 (19)
C30	0.182 (3)	0.0733 (17)	0.0754 (16)	−0.0030 (19)	0.0314 (19)	−0.0039 (13)
O2	0.0979 (11)	0.0883 (11)	0.0762 (11)	−0.0292 (9)	0.0213 (9)	−0.0268 (9)

Geometric parameters (Å, º) top

C1—C2	1.381 (2)	C16—C17	1.380 (3)
C1—C6	1.385 (2)	C16—C21	1.385 (3)
C1—C7	1.489 (2)	C16—C22	1.491 (3)
C2—C3	1.385 (3)	C17—C18	1.379 (3)
C2—H2	0.96 (2)	C17—H17	0.94 (2)
C3—C4	1.372 (2)	C18—C19	1.373 (3)
C3—H3	0.97 (2)	C18—H18	0.92 (2)
C4—C5	1.382 (2)	C19—C20	1.379 (3)
C4—C13	1.523 (2)	C19—C28	1.518 (3)
C5—C6	1.377 (3)	C20—C21	1.370 (3)
C5—H5	0.97 (2)	C20—H20	0.97 (2)
C6—H6	0.93 (2)	C21—H21	0.96 (2)
C7—C8	1.383 (2)	C22—C27	1.379 (3)
C7—C12	1.388 (3)	C22—C23	1.384 (3)
C8—C9	1.383 (3)	C23—C24	1.376 (3)
C8—H8	0.94 (2)	C23—H23	0.98 (2)
C9—C10	1.362 (3)	C24—C25	1.357 (4)
C9—H9	0.95 (2)	C24—H24	0.94 (3)
C10—C11	1.369 (3)	C25—C26	1.354 (4)
C10—H10	0.98 (2)	C25—H25	1.03 (2)
C11—C12	1.380 (3)	C26—C27	1.382 (3)
C11—H11	0.98 (2)	C26—H26	0.99 (3)
C12—H12	0.97 (2)	C27—H27	0.93 (2)
C13—O1	1.445 (2)	C28—O2	1.437 (2)
C13—C15	1.518 (3)	C28—C29	1.521 (3)
C13—C14	1.520 (3)	C28—C30	1.527 (3)
C14—H14A	1.04 (3)	C29—H29A	1.01 (4)
C14—H14B	1.00 (3)	C29—H29B	0.97 (4)
C14—H14C	0.97 (3)	C29—H29C	1.00 (3)
C15—H15A	1.04 (3)	C30—H30A	0.98 (4)
C15—H15B	1.01 (3)	C30—H30B	0.96 (3)
C15—H15C	1.01 (3)	C30—H30C	1.01 (4)
O1—H1A	0.900 (10)	O2—H2A	0.895 (10)
O1—H1B	0.87 (3)	O2—H2B	0.893 (10)

C2—C1—C6	116.10 (16)	C17—C16—C21	115.77 (19)
C2—C1—C7	121.57 (15)	C17—C16—C22	122.35 (17)
C6—C1—C7	122.32 (15)	C21—C16—C22	121.87 (17)
C1—C2—C3	121.83 (17)	C18—C17—C16	121.90 (19)
C1—C2—H2	119.8 (12)	C18—C17—H17	121.1 (13)
C3—C2—H2	118.4 (12)	C16—C17—H17	117.0 (14)
C4—C3—C2	121.75 (17)	C19—C18—C17	122.01 (19)
C4—C3—H3	120.2 (12)	C19—C18—H18	118.4 (14)
C2—C3—H3	118.0 (12)	C17—C18—H18	119.2 (14)
C3—C4—C5	116.69 (16)	C18—C19—C20	116.20 (19)
C3—C4—C13	123.36 (16)	C18—C19—C28	122.48 (17)
C5—C4—C13	119.96 (16)	C20—C19—C28	121.16 (17)
C6—C5—C4	121.73 (17)	C21—C20—C19	122.00 (19)
C6—C5—H5	118.5 (12)	C21—C20—H20	120.8 (13)
C4—C5—H5	119.7 (12)	C19—C20—H20	117.2 (13)
C5—C6—C1	121.90 (17)	C20—C21—C16	122.09 (19)
C5—C6—H6	118.7 (12)	C20—C21—H21	119.2 (13)
C1—C6—H6	119.4 (12)	C16—C21—H21	118.6 (13)
C8—C7—C12	116.94 (17)	C27—C22—C23	115.7 (2)
C8—C7—C1	122.00 (16)	C27—C22—C16	122.54 (18)
C12—C7—C1	121.06 (16)	C23—C22—C16	121.79 (18)
C9—C8—C7	121.3 (2)	C24—C23—C22	121.9 (2)
C9—C8—H8	120.7 (13)	C24—C23—H23	122.5 (14)
C7—C8—H8	118.1 (13)	C22—C23—H23	115.4 (14)
C10—C9—C8	120.6 (2)	C25—C24—C23	120.9 (2)
C10—C9—H9	122.5 (14)	C25—C24—H24	118.5 (17)
C8—C9—H9	116.8 (14)	C23—C24—H24	120.4 (17)
C9—C10—C11	119.5 (2)	C26—C25—C24	118.7 (3)
C9—C10—H10	119.6 (13)	C26—C25—H25	120.4 (13)
C11—C10—H10	121.0 (13)	C24—C25—H25	120.9 (13)
C10—C11—C12	120.0 (2)	C25—C26—C27	120.6 (2)
C10—C11—H11	121.4 (13)	C25—C26—H26	121.5 (15)
C12—C11—H11	118.6 (13)	C27—C26—H26	117.8 (15)
C11—C12—C7	121.67 (19)	C22—C27—C26	122.1 (2)
C11—C12—H12	119.8 (12)	C22—C27—H27	116.9 (15)
C7—C12—H12	118.5 (12)	C26—C27—H27	121.0 (15)
O1—C13—C15	107.35 (17)	O2—C28—C19	110.14 (15)
O1—C13—C14	108.02 (16)	O2—C28—C29	108.26 (18)
C15—C13—C14	109.97 (18)	C19—C28—C29	112.9 (2)
O1—C13—C4	107.11 (14)	O2—C28—C30	106.0 (2)
C15—C13—C4	110.96 (16)	C19—C28—C30	108.45 (18)
C14—C13—C4	113.18 (16)	C29—C28—C30	110.8 (2)
C13—C14—H14A	111.6 (14)	C28—C29—H29A	106.7 (19)
C13—C14—H14B	108.9 (15)	C28—C29—H29B	108 (2)
H14A—C14—H14B	108 (2)	H29A—C29—H29B	107 (3)
C13—C14—H14C	110.4 (16)	C28—C29—H29C	104 (2)
H14A—C14—H14C	111 (2)	H29A—C29—H29C	116 (3)
H14B—C14—H14C	107 (2)	H29B—C29—H29C	114 (3)
C13—C15—H15A	110.6 (15)	C28—C30—H30A	108 (2)
C13—C15—H15B	109.9 (17)	C28—C30—H30B	107 (2)
H15A—C15—H15B	109 (2)	H30A—C30—H30B	113 (3)
C13—C15—H15C	109.8 (16)	C28—C30—H30C	105 (2)
H15A—C15—H15C	110 (2)	H30A—C30—H30C	114 (3)
H15B—C15—H15C	107 (2)	H30B—C30—H30C	109 (3)
C13—O1—H1A	100 (3)	C28—O2—H2A	102 (3)
C13—O1—H1B	114 (3)	C28—O2—H2B	117 (3)
H1A—O1—H1B	114 (4)	H2A—O2—H2B	111 (5)

C6—C1—C2—C3	−0.2 (3)	C21—C16—C17—C18	1.6 (3)
C7—C1—C2—C3	−179.76 (17)	C22—C16—C17—C18	−177.0 (2)
C1—C2—C3—C4	0.6 (3)	C16—C17—C18—C19	−0.2 (4)
C2—C3—C4—C5	−0.3 (3)	C17—C18—C19—C20	−1.6 (3)
C2—C3—C4—C13	179.94 (18)	C17—C18—C19—C28	173.9 (2)
C3—C4—C5—C6	−0.3 (3)	C18—C19—C20—C21	1.8 (3)
C13—C4—C5—C6	179.45 (18)	C28—C19—C20—C21	−173.8 (2)
C4—C5—C6—C1	0.7 (3)	C19—C20—C21—C16	−0.3 (4)
C2—C1—C6—C5	−0.4 (3)	C17—C16—C21—C20	−1.4 (3)
C7—C1—C6—C5	179.15 (18)	C22—C16—C21—C20	177.3 (2)
C2—C1—C7—C8	171.37 (18)	C17—C16—C22—C27	−9.5 (3)
C6—C1—C7—C8	−8.1 (3)	C21—C16—C22—C27	171.9 (2)
C2—C1—C7—C12	−7.8 (3)	C17—C16—C22—C23	169.1 (2)
C6—C1—C7—C12	172.69 (18)	C21—C16—C22—C23	−9.5 (3)
C12—C7—C8—C9	0.2 (3)	C27—C22—C23—C24	−1.4 (4)
C1—C7—C8—C9	−178.97 (19)	C16—C22—C23—C24	179.9 (2)
C7—C8—C9—C10	−0.2 (4)	C22—C23—C24—C25	1.3 (4)
C8—C9—C10—C11	−0.1 (4)	C23—C24—C25—C26	0.0 (4)
C9—C10—C11—C12	0.3 (4)	C24—C25—C26—C27	−1.0 (4)
C10—C11—C12—C7	−0.2 (3)	C23—C22—C27—C26	0.3 (3)
C8—C7—C12—C11	0.0 (3)	C16—C22—C27—C26	179.0 (2)
C1—C7—C12—C11	179.18 (18)	C25—C26—C27—C22	0.9 (4)
C3—C4—C13—O1	−125.65 (18)	C18—C19—C28—O2	23.1 (3)
C5—C4—C13—O1	54.6 (2)	C20—C19—C28—O2	−161.64 (19)
C3—C4—C13—C15	117.5 (2)	C18—C19—C28—C29	144.2 (2)
C5—C4—C13—C15	−62.3 (2)	C20—C19—C28—C29	−40.5 (3)
C3—C4—C13—C14	−6.7 (3)	C18—C19—C28—C30	−92.5 (3)
C5—C4—C13—C14	173.51 (19)	C20—C19—C28—C30	82.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.90 (1)	1.99 (2)	2.804 (2)	150 (4)
O2—H2A···O1	0.90 (1)	2.09 (4)	2.804 (2)	136 (4)
O1—H1B···O1ⁱ	0.87 (3)	1.90 (3)	2.767 (3)	174 (4)
O2—H2B···O2ⁱ	0.89 (1)	2.03 (1)	2.926 (3)	177 (4)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆O
M_r	212.28
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	295
a, b, c (Å)	12.4406 (14), 15.5754 (18), 25.741 (3)
β (°)	102.332 (2)
V (Å³)	4872.7 (10)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.46 × 0.36 × 0.08

Data collection
Diffractometer	Bruker P4 diffractometer with SMART 1000 CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.931, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	12927, 4590, 2859
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.147, 1.01
No. of reflections	4590
No. of parameters	391
No. of restraints	3
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.14

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008) and SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), Mercury (Macrae et al., 2008) and POV-RAY (Cason, 2004), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.900 (10)	1.99 (2)	2.804 (2)	150 (4)
O2—H2A···O1	0.895 (10)	2.09 (4)	2.804 (2)	136 (4)
O1—H1B···O1ⁱ	0.87 (3)	1.90 (3)	2.767 (3)	174 (4)
O2—H2B···O2ⁱ	0.893 (10)	2.034 (11)	2.926 (3)	177 (4)

Symmetry code: (i) −x, y, −z+1/2.

Acknowledgements

The authors thank the University of Pretoria for financial support.

References

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