2-(2-Benzyl-phen-yl)propan-2-ol.

There are two mol-ecules in the asymmetric unit of the title compound, C(16)H(18)O, a tertiary alcohol featuring a 2-benzyl-phenyl substituent. Co-operative O-H⋯O hydrogen bonds connect the mol-ecules into tetra-mers.

Related literature

For general background to the use of benzhydrols in pharmaceutical synthesis, see: Ohkuma et al. (2000 ▶). For related structures, see: Ferguson et al. (1995 ▶); Fun et al. (2010 ▶); Siddaraju et al. (2010 ▶, 2011 ▶); Zeng & Liu (2010 ▶); Gu et al. (2009 ▶). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H18O

M = 226.30

Monoclinic,

a = 12.2252 (3) Å

b = 17.2508 (4) Å

c = 16.7784 (3) Å

β = 132.549 (1)°

V = 2606.79 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 200 K

0.59 × 0.51 × 0.34 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.901, T max = 1.000

24429 measured reflections

6480 independent reflections

5035 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.148

S = 1.05

6480 reflections

311 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047143/hg5130sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811047143/hg5130Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047143/hg5130Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536811047143/hg5130Isup4.cml

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

C16H18O	F(000) = 976
Mr = 226.30	Dx = 1.153 Mg m−3
Monoclinic, P21/c	Melting point = 333–335 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.2252 (3) Å	Cell parameters from 9880 reflections
b = 17.2508 (4) Å	θ = 2.6–28.3°
c = 16.7784 (3) Å	µ = 0.07 mm−1
β = 132.549 (1)°	T = 200 K
V = 2606.79 (10) Å3	Block, colourless
Z = 8	0.59 × 0.51 × 0.34 mm

Bruker APEXII CCD diffractometer	6480 independent reflections
Radiation source: fine-focus sealed tube	5035 reflections with I > 2σ(I)
graphite	Rint = 0.015
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→16
Tmin = 0.901, Tmax = 1.000	k = −23→21
24429 measured reflections	l = −22→20

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.148	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.964P] where P = (Fo2 + 2Fc2)/3
6480 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.57 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.57510 (11)	−0.02752 (6)	0.13404 (8)	0.0415 (2)
H1	0.4865	−0.0134	0.0848	0.062*
C1	0.61107 (17)	−0.03064 (8)	0.23555 (12)	0.0402 (3)
C2	0.77983 (18)	−0.02453 (11)	0.32472 (13)	0.0528 (4)
H2A	0.8256	−0.0677	0.3183	0.079*
H2B	0.8096	−0.0267	0.3955	0.079*
H2C	0.8126	0.0247	0.3176	0.079*
C3	0.5637 (2)	−0.11099 (9)	0.24153 (17)	0.0610 (5)
H3A	0.4554	−0.1156	0.1850	0.092*
H3B	0.5955	−0.1179	0.3126	0.092*
H3C	0.6098	−0.1509	0.2308	0.092*
C4	0.6403 (3)	0.13895 (10)	0.2002 (2)	0.0778 (7)
H4A	0.7456	0.1355	0.2687	0.093*
H4B	0.6259	0.1020	0.1487	0.093*
C11	0.53379 (15)	0.03600 (8)	0.24184 (11)	0.0357 (3)
C12	0.45154 (19)	0.01992 (9)	0.26930 (13)	0.0477 (4)
H12	0.4452	−0.0323	0.2840	0.057*
C13	0.3783 (2)	0.07688 (10)	0.27620 (14)	0.0505 (4)
H13	0.3235	0.0637	0.2956	0.061*
C14	0.38553 (18)	0.15206 (9)	0.25495 (13)	0.0458 (3)
H14	0.3343	0.1916	0.2579	0.055*
C15	0.46826 (19)	0.16975 (9)	0.22906 (15)	0.0499 (4)
H15	0.4744	0.2223	0.2155	0.060*
C16	0.54339 (17)	0.11350 (8)	0.22197 (13)	0.0428 (3)
C21	0.61156 (17)	0.21996 (8)	0.15524 (13)	0.0428 (3)
C22	0.70386 (17)	0.27937 (10)	0.22356 (13)	0.0495 (4)
H22	0.7828	0.2697	0.2987	0.059*
C23	0.6818 (2)	0.35404 (11)	0.1827 (2)	0.0677 (6)
H23	0.7459	0.3952	0.2294	0.081*
C24	0.5661 (3)	0.36713 (14)	0.0742 (2)	0.0802 (8)
H24	0.5495	0.4177	0.0455	0.096*
C25	0.4755 (3)	0.30789 (18)	0.00804 (18)	0.0823 (8)
H25	0.3949	0.3173	−0.0669	0.099*
C26	0.49900 (19)	0.23568 (14)	0.04793 (15)	0.0637 (5)
H26	0.4355	0.1948	0.0000	0.076*
O2	0.70453 (11)	−0.02771 (7)	0.04946 (8)	0.0462 (3)
H2	0.6841	−0.0321	0.0880	0.069*
C5	0.85971 (15)	−0.04565 (9)	0.11354 (12)	0.0438 (3)
C6	0.8862 (2)	−0.04113 (13)	0.03673 (15)	0.0625 (5)
H6A	0.8188	−0.0769	−0.0239	0.094*
H6B	0.9892	−0.0555	0.0757	0.094*
H6C	0.8677	0.0119	0.0091	0.094*
C7	0.8837 (2)	−0.12903 (10)	0.15236 (17)	0.0607 (5)
H7A	0.8622	−0.1333	0.1989	0.091*
H7B	0.9870	−0.1440	0.1933	0.091*
H7C	0.8172	−0.1634	0.0898	0.091*
C8	0.81113 (17)	0.13174 (10)	0.07974 (14)	0.0516 (4)
H8A	0.7657	0.0919	0.0226	0.062*
H8B	0.7324	0.1520	0.0765	0.062*
C31	0.95608 (15)	0.01350 (9)	0.20631 (11)	0.0376 (3)
C32	1.07226 (16)	−0.01306 (10)	0.31153 (12)	0.0449 (3)
H32	1.0915	−0.0671	0.3237	0.054*
C33	1.16028 (18)	0.03729 (11)	0.39872 (13)	0.0538 (4)
H33	1.2398	0.0179	0.4693	0.065*
C34	1.1315 (2)	0.11554 (12)	0.38212 (14)	0.0579 (4)
H34	1.1888	0.1504	0.4415	0.069*
C35	1.01901 (19)	0.14296 (10)	0.27878 (14)	0.0530 (4)
H35	1.0008	0.1972	0.2679	0.064*
C36	0.93098 (16)	0.09365 (9)	0.18956 (12)	0.0416 (3)
C41	0.86805 (17)	0.19740 (9)	0.05614 (12)	0.0436 (3)
C42	0.7984 (2)	0.26888 (10)	0.02209 (14)	0.0553 (4)
H42	0.7161	0.2775	0.0159	0.066*
C43	0.8475 (3)	0.32829 (10)	−0.00309 (15)	0.0645 (5)
H43	0.7988	0.3771	−0.0261	0.077*
C44	0.9662 (2)	0.31676 (11)	0.00512 (14)	0.0609 (5)
H44	0.9992	0.3573	−0.0127	0.073*
C45	1.0364 (2)	0.24642 (12)	0.03907 (15)	0.0602 (5)
H45	1.1188	0.2382	0.0452	0.072*
C46	0.98818 (18)	0.18725 (10)	0.06445 (14)	0.0523 (4)
H46	1.0381	0.1387	0.0880	0.063*

	U11	U22	U33	U12	U13	U23
O1	0.0422 (5)	0.0485 (6)	0.0408 (5)	0.0068 (4)	0.0309 (5)	0.0031 (4)
C1	0.0500 (8)	0.0371 (7)	0.0435 (7)	0.0075 (6)	0.0357 (7)	0.0070 (6)
C2	0.0503 (9)	0.0608 (10)	0.0449 (8)	0.0198 (8)	0.0312 (8)	0.0135 (7)
C3	0.0907 (14)	0.0371 (8)	0.0856 (13)	0.0084 (8)	0.0718 (12)	0.0095 (8)
C4	0.1053 (16)	0.0417 (9)	0.155 (2)	0.0107 (10)	0.1157 (18)	0.0167 (11)
C11	0.0390 (7)	0.0374 (7)	0.0348 (6)	0.0026 (5)	0.0266 (6)	0.0025 (5)
C12	0.0650 (10)	0.0435 (8)	0.0574 (9)	0.0039 (7)	0.0505 (9)	0.0076 (7)
C13	0.0627 (10)	0.0563 (9)	0.0594 (9)	0.0027 (8)	0.0521 (9)	0.0028 (7)
C14	0.0511 (8)	0.0482 (8)	0.0511 (8)	0.0061 (7)	0.0397 (8)	−0.0009 (7)
C15	0.0612 (10)	0.0369 (7)	0.0721 (11)	0.0035 (7)	0.0534 (9)	0.0023 (7)
C16	0.0488 (8)	0.0370 (7)	0.0592 (9)	0.0019 (6)	0.0431 (8)	0.0027 (6)
C21	0.0469 (8)	0.0382 (7)	0.0617 (9)	0.0000 (6)	0.0441 (8)	0.0013 (6)
C22	0.0394 (8)	0.0564 (9)	0.0490 (8)	0.0028 (7)	0.0284 (7)	−0.0002 (7)
C23	0.0699 (12)	0.0452 (9)	0.1210 (18)	−0.0125 (9)	0.0779 (14)	−0.0186 (10)
C24	0.1033 (17)	0.0689 (13)	0.131 (2)	0.0483 (13)	0.1041 (18)	0.0576 (14)
C25	0.0711 (13)	0.130 (2)	0.0627 (12)	0.0475 (15)	0.0519 (12)	0.0401 (14)
C26	0.0414 (8)	0.0981 (15)	0.0513 (9)	−0.0025 (9)	0.0312 (8)	−0.0142 (10)
O2	0.0325 (5)	0.0694 (7)	0.0390 (5)	−0.0031 (5)	0.0250 (4)	−0.0037 (5)
C5	0.0329 (7)	0.0575 (9)	0.0430 (7)	−0.0033 (6)	0.0264 (6)	−0.0094 (6)
C6	0.0501 (9)	0.0949 (14)	0.0561 (10)	−0.0121 (9)	0.0413 (9)	−0.0238 (9)
C7	0.0496 (9)	0.0517 (10)	0.0764 (12)	−0.0062 (8)	0.0407 (9)	−0.0144 (9)
C8	0.0389 (8)	0.0609 (10)	0.0589 (9)	0.0083 (7)	0.0346 (8)	0.0143 (8)
C31	0.0324 (6)	0.0485 (8)	0.0387 (7)	−0.0004 (6)	0.0267 (6)	−0.0020 (6)
C32	0.0381 (7)	0.0542 (9)	0.0436 (8)	0.0022 (6)	0.0281 (7)	0.0033 (6)
C33	0.0401 (8)	0.0783 (12)	0.0377 (8)	−0.0057 (8)	0.0242 (7)	−0.0019 (7)
C34	0.0540 (9)	0.0730 (12)	0.0513 (9)	−0.0205 (9)	0.0375 (8)	−0.0225 (8)
C35	0.0561 (9)	0.0486 (9)	0.0644 (10)	−0.0069 (7)	0.0448 (9)	−0.0094 (7)
C36	0.0372 (7)	0.0492 (8)	0.0463 (8)	0.0002 (6)	0.0314 (7)	0.0001 (6)
C41	0.0424 (7)	0.0478 (8)	0.0458 (8)	0.0049 (6)	0.0319 (7)	0.0033 (6)
C42	0.0642 (10)	0.0543 (10)	0.0572 (10)	0.0153 (8)	0.0450 (9)	0.0058 (8)
C43	0.0912 (14)	0.0414 (9)	0.0548 (10)	0.0062 (9)	0.0469 (11)	0.0019 (7)
C44	0.0717 (12)	0.0561 (10)	0.0462 (9)	−0.0214 (9)	0.0364 (9)	−0.0070 (8)
C45	0.0528 (10)	0.0733 (12)	0.0604 (10)	−0.0111 (9)	0.0406 (9)	−0.0002 (9)
C46	0.0474 (9)	0.0530 (9)	0.0646 (10)	0.0060 (7)	0.0412 (8)	0.0072 (8)

O1—C1	1.4437 (16)	O2—C5	1.4464 (17)
O1—H1	0.8400	O2—H2	0.8399
C1—C2	1.527 (2)	C5—C7	1.523 (2)
C1—C3	1.531 (2)	C5—C6	1.529 (2)
C1—C11	1.5364 (19)	C5—C31	1.540 (2)
C2—H2A	0.9800	C6—H6A	0.9800
C2—H2B	0.9800	C6—H6B	0.9800
C2—H2C	0.9800	C6—H6C	0.9800
C3—H3A	0.9800	C7—H7A	0.9800
C3—H3B	0.9800	C7—H7B	0.9800
C3—H3C	0.9800	C7—H7C	0.9800
C4—C21	1.512 (2)	C8—C41	1.515 (2)
C4—C16	1.522 (2)	C8—C36	1.524 (2)
C4—H4A	0.9900	C8—H8A	0.9900
C4—H4B	0.9900	C8—H8B	0.9900
C11—C12	1.3881 (19)	C31—C32	1.397 (2)
C11—C16	1.4018 (19)	C31—C36	1.403 (2)
C12—C13	1.386 (2)	C32—C33	1.387 (2)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.364 (2)	C33—C34	1.375 (3)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.378 (2)	C34—C35	1.377 (3)
C14—H14	0.9500	C34—H34	0.9500
C15—C16	1.396 (2)	C35—C36	1.394 (2)
C15—H15	0.9500	C35—H35	0.9500
C21—C26	1.363 (2)	C41—C42	1.384 (2)
C21—C22	1.374 (2)	C41—C46	1.389 (2)
C22—C23	1.397 (3)	C42—C43	1.390 (3)
C22—H22	0.9500	C42—H42	0.9500
C23—C24	1.372 (3)	C43—C44	1.377 (3)
C23—H23	0.9500	C43—H43	0.9500
C24—C25	1.357 (4)	C44—C45	1.368 (3)
C24—H24	0.9500	C44—H44	0.9500
C25—C26	1.350 (3)	C45—C46	1.382 (2)
C25—H25	0.9500	C45—H45	0.9500
C26—H26	0.9500	C46—H46	0.9500
C1—O1—H1	109.4	C5—O2—H2	109.3
O1—C1—C2	106.57 (12)	O2—C5—C7	107.22 (12)
O1—C1—C3	106.50 (13)	O2—C5—C6	106.36 (13)
C2—C1—C3	108.58 (14)	C7—C5—C6	108.63 (14)
O1—C1—C11	110.01 (11)	O2—C5—C31	109.39 (11)
C2—C1—C11	111.55 (12)	C7—C5—C31	113.51 (13)
C3—C1—C11	113.30 (12)	C6—C5—C31	111.40 (12)
C1—C2—H2A	109.5	C5—C6—H6A	109.5
C1—C2—H2B	109.5	C5—C6—H6B	109.5
H2A—C2—H2B	109.5	H6A—C6—H6B	109.5
C1—C2—H2C	109.5	C5—C6—H6C	109.5
H2A—C2—H2C	109.5	H6A—C6—H6C	109.5
H2B—C2—H2C	109.5	H6B—C6—H6C	109.5
C1—C3—H3A	109.5	C5—C7—H7A	109.5
C1—C3—H3B	109.5	C5—C7—H7B	109.5
H3A—C3—H3B	109.5	H7A—C7—H7B	109.5
C1—C3—H3C	109.5	C5—C7—H7C	109.5
H3A—C3—H3C	109.5	H7A—C7—H7C	109.5
H3B—C3—H3C	109.5	H7B—C7—H7C	109.5
C21—C4—C16	115.49 (14)	C41—C8—C36	113.72 (13)
C21—C4—H4A	108.4	C41—C8—H8A	108.8
C16—C4—H4A	108.4	C36—C8—H8A	108.8
C21—C4—H4B	108.4	C41—C8—H8B	108.8
C16—C4—H4B	108.4	C36—C8—H8B	108.8
H4A—C4—H4B	107.5	H8A—C8—H8B	107.7
C12—C11—C16	117.75 (13)	C32—C31—C36	118.29 (13)
C12—C11—C1	119.36 (12)	C32—C31—C5	119.27 (14)
C16—C11—C1	122.89 (12)	C36—C31—C5	122.44 (13)
C13—C12—C11	122.68 (14)	C33—C32—C31	121.87 (16)
C13—C12—H12	118.7	C33—C32—H32	119.1
C11—C12—H12	118.7	C31—C32—H32	119.1
C14—C13—C12	119.51 (14)	C34—C33—C32	119.43 (16)
C14—C13—H13	120.2	C34—C33—H33	120.3
C12—C13—H13	120.2	C32—C33—H33	120.3
C13—C14—C15	118.97 (14)	C33—C34—C35	119.54 (16)
C13—C14—H14	120.5	C33—C34—H34	120.2
C15—C14—H14	120.5	C35—C34—H34	120.2
C14—C15—C16	122.58 (15)	C34—C35—C36	122.06 (17)
C14—C15—H15	118.7	C34—C35—H35	119.0
C16—C15—H15	118.7	C36—C35—H35	119.0
C15—C16—C11	118.50 (13)	C35—C36—C31	118.74 (14)
C15—C16—C4	118.95 (14)	C35—C36—C8	116.63 (15)
C11—C16—C4	122.44 (13)	C31—C36—C8	124.63 (14)
C26—C21—C22	118.66 (16)	C42—C41—C46	117.88 (15)
C26—C21—C4	121.96 (18)	C42—C41—C8	120.72 (14)
C22—C21—C4	119.35 (17)	C46—C41—C8	121.37 (14)
C21—C22—C23	120.08 (17)	C41—C42—C43	120.72 (17)
C21—C22—H22	120.0	C41—C42—H42	119.6
C23—C22—H22	120.0	C43—C42—H42	119.6
C24—C23—C22	119.11 (19)	C44—C43—C42	120.39 (17)
C24—C23—H23	120.4	C44—C43—H43	119.8
C22—C23—H23	120.4	C42—C43—H43	119.8
C25—C24—C23	120.03 (18)	C45—C44—C43	119.46 (17)
C25—C24—H24	120.0	C45—C44—H44	120.3
C23—C24—H24	120.0	C43—C44—H44	120.3
C26—C25—C24	120.5 (2)	C44—C45—C46	120.31 (17)
C26—C25—H25	119.8	C44—C45—H45	119.8
C24—C25—H25	119.8	C46—C45—H45	119.8
C25—C26—C21	121.7 (2)	C45—C46—C41	121.23 (16)
C25—C26—H26	119.2	C45—C46—H46	119.4
C21—C26—H26	119.2	C41—C46—H46	119.4
O1—C1—C11—C12	129.43 (14)	O2—C5—C31—C32	131.82 (13)
C2—C1—C11—C12	−112.53 (16)	C7—C5—C31—C32	12.12 (18)
C3—C1—C11—C12	10.4 (2)	C6—C5—C31—C32	−110.88 (16)
O1—C1—C11—C16	−51.21 (18)	O2—C5—C31—C36	−47.57 (17)
C2—C1—C11—C16	66.83 (18)	C7—C5—C31—C36	−167.27 (13)
C3—C1—C11—C16	−170.28 (15)	C6—C5—C31—C36	69.72 (18)
C16—C11—C12—C13	0.9 (2)	C36—C31—C32—C33	1.1 (2)
C1—C11—C12—C13	−179.75 (15)	C5—C31—C32—C33	−178.27 (13)
C11—C12—C13—C14	0.3 (3)	C31—C32—C33—C34	1.2 (2)
C12—C13—C14—C15	−1.2 (3)	C32—C33—C34—C35	−2.2 (2)
C13—C14—C15—C16	1.1 (3)	C33—C34—C35—C36	0.9 (2)
C14—C15—C16—C11	0.1 (3)	C34—C35—C36—C31	1.4 (2)
C14—C15—C16—C4	−176.00 (18)	C34—C35—C36—C8	−179.60 (14)
C12—C11—C16—C15	−1.0 (2)	C32—C31—C36—C35	−2.39 (19)
C1—C11—C16—C15	179.59 (14)	C5—C31—C36—C35	177.01 (12)
C12—C11—C16—C4	174.93 (18)	C32—C31—C36—C8	178.73 (12)
C1—C11—C16—C4	−4.4 (3)	C5—C31—C36—C8	−1.9 (2)
C21—C4—C16—C15	−17.7 (3)	C41—C8—C36—C35	51.16 (19)
C21—C4—C16—C11	166.40 (17)	C41—C8—C36—C31	−129.93 (15)
C16—C4—C21—C26	−81.9 (2)	C36—C8—C41—C42	−129.26 (16)
C16—C4—C21—C22	100.1 (2)	C36—C8—C41—C46	52.9 (2)
C26—C21—C22—C23	−0.2 (2)	C46—C41—C42—C43	0.1 (3)
C4—C21—C22—C23	177.91 (14)	C8—C41—C42—C43	−177.79 (16)
C21—C22—C23—C24	0.8 (2)	C41—C42—C43—C44	0.2 (3)
C22—C23—C24—C25	−0.3 (3)	C42—C43—C44—C45	−0.5 (3)
C23—C24—C25—C26	−0.7 (3)	C43—C44—C45—C46	0.3 (3)
C24—C25—C26—C21	1.3 (3)	C44—C45—C46—C41	0.1 (3)
C22—C21—C26—C25	−0.8 (2)	C42—C41—C46—C45	−0.3 (3)
C4—C21—C26—C25	−178.88 (16)	C8—C41—C46—C45	177.62 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.84	1.98	2.7997 (14)	166.
O2—H2···O1	0.84	1.94	2.7486 (14)	161.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.84	1.98	2.7997 (14)	166
O2—H2⋯O1	0.84	1.94	2.7486 (14)	161

Symmetry code: (i) .