1-(3-Benzyl-4,6-dibenz-yloxy-2-hy-droxy-phen-yl)ethanone.

The title compound, C(29)H(26)O(4), is essentially planar in the acetophenone portion that includes both the hy-droxy and a benz-yloxy O atoms, with an r.m.s. deviation of 0.0311 Å. The other two substituents inter-sect the plane at 70.45 (3) and 59.55 (4)°. In the molecule there is an intramolecular O-H⋯O hydrogen bond. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, as well as C-H⋯π and π-stacking inter-actions, with centroid-centroid distances 3.6570 (2) Å.

Related literature

For applications of acetophenones, see: Burdock (2010 ▶); Marais et al. (2005 ▶).

Experimental

Crystal data

C29H26O4

M = 438.5

Triclinic,

a = 8.2349 (5) Å

b = 10.5411 (7) Å

c = 13.5115 (9) Å

α = 93.412 (3)°

β = 94.139 (3)°

γ = 105.102 (3)°

V = 1125.66 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.39 × 0.12 × 0.03 mm

Data collection

Bruker X8 APEXII 4K KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.968, T max = 0.997

22325 measured reflections

5521 independent reflections

4071 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.107

S = 1.03

5521 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681203588X/ng5288sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203588X/ng5288Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203588X/ng5288Isup3.cml

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

C29H26O4	Z = 2
Mr = 438.5	F(000) = 464
Triclinic, P1	Dx = 1.294 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2349 (5) Å	Cell parameters from 5873 reflections
b = 10.5411 (7) Å	θ = 2.4–28.1°
c = 13.5115 (9) Å	µ = 0.09 mm−1
α = 93.412 (3)°	T = 100 K
β = 94.139 (3)°	Plate, colourless
γ = 105.102 (3)°	0.39 × 0.12 × 0.03 mm
V = 1125.66 (13) Å3

Bruker X8 APEXII 4K KappaCCD diffractometer	5521 independent reflections
Radiation source: sealed tube	4071 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 512 pixels mm-1	θmax = 28.3°, θmin = 2.0°
φ and ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −14→13
Tmin = 0.968, Tmax = 0.997	l = −17→17
22325 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.2817P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.107	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.31 e Å−3
5521 reflections	Δρmin = −0.22 e Å−3
300 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.43123 (15)	1.16936 (12)	1.05832 (9)	0.0158 (3)
C2	0.43202 (14)	1.13497 (12)	0.95515 (9)	0.0154 (3)
C3	0.30811 (15)	1.01942 (12)	0.91394 (9)	0.0151 (3)
C4	0.19200 (14)	0.94574 (12)	0.97185 (9)	0.0158 (3)
H4	0.1099	0.8689	0.9431	0.019*
C5	0.19676 (14)	0.98530 (12)	1.07249 (9)	0.0152 (3)
C6	0.31383 (15)	1.09821 (12)	1.11786 (9)	0.0153 (3)
C22	0.55812 (15)	1.21880 (12)	0.89903 (10)	0.0170 (3)
C23	0.56585 (17)	1.19593 (13)	0.78917 (10)	0.0215 (3)
H23A	0.6572	1.2653	0.7672	0.032*
H23B	0.4581	1.1976	0.7541	0.032*
H23C	0.5873	1.1099	0.7744	0.032*
C31	0.22496 (15)	0.85555 (13)	0.66335 (9)	0.0194 (3)
C32	0.27035 (17)	0.74395 (14)	0.63042 (11)	0.0254 (3)
H32	0.2723	0.6771	0.6743	0.031*
C33	0.3130 (2)	0.72889 (16)	0.53403 (12)	0.0343 (4)
H33	0.3438	0.6518	0.5121	0.041*
C34	0.3109 (2)	0.82508 (17)	0.46990 (12)	0.0418 (4)
H34	0.3415	0.8151	0.404	0.05*
C35	0.2642 (3)	0.93618 (17)	0.50191 (12)	0.0454 (5)
H35	0.2619	1.0026	0.4577	0.054*
C36	0.2208 (2)	0.95114 (15)	0.59800 (11)	0.0329 (4)
H36	0.1879	1.0276	0.6193	0.039*
C37	0.18315 (16)	0.87355 (13)	0.76859 (10)	0.0210 (3)
H37A	0.0707	0.8907	0.7697	0.025*
H37B	0.182	0.7934	0.8035	0.025*
C51	−0.11328 (15)	0.72877 (12)	1.18251 (10)	0.0167 (3)
C52	−0.25410 (16)	0.62077 (13)	1.16099 (10)	0.0213 (3)
H52	−0.2897	0.5881	1.0937	0.026*
C53	−0.34264 (17)	0.56061 (13)	1.23669 (11)	0.0250 (3)
H53	−0.4384	0.4872	1.2212	0.03*
C54	−0.29123 (17)	0.60767 (13)	1.33487 (11)	0.0247 (3)
H54	−0.3526	0.5674	1.3868	0.03*
C55	−0.15038 (17)	0.71347 (13)	1.35738 (10)	0.0241 (3)
H55	−0.114	0.7449	1.4248	0.029*
C56	−0.06189 (16)	0.77387 (13)	1.28112 (10)	0.0210 (3)
H56	0.0345	0.8466	1.2969	0.025*
C57	−0.02121 (15)	0.79066 (12)	1.09773 (9)	0.0167 (3)
H57A	0.0447	0.7329	1.07	0.02*
H57B	−0.1032	0.8025	1.0441	0.02*
C61	0.25514 (15)	1.26065 (12)	1.25126 (9)	0.0171 (3)
C62	0.23856 (17)	1.29554 (13)	1.35037 (10)	0.0237 (3)
H62	0.2714	1.2461	1.401	0.028*
C63	0.17508 (19)	1.40109 (14)	1.37632 (11)	0.0299 (3)
H63	0.1636	1.4227	1.4443	0.036*
C64	0.12837 (18)	1.47526 (14)	1.30383 (11)	0.0281 (3)
H64	0.0845	1.5475	1.3217	0.034*
C65	0.14603 (17)	1.44345 (13)	1.20536 (11)	0.0240 (3)
H65	0.115	1.4943	1.1552	0.029*
C66	0.20922 (15)	1.33692 (12)	1.17949 (10)	0.0194 (3)
H66	0.2211	1.316	1.1115	0.023*
C67	0.32122 (16)	1.14155 (12)	1.22660 (9)	0.0179 (3)
H67A	0.4402	1.1616	1.255	0.022*
H67B	0.2559	1.0666	1.2604	0.022*
O1	0.54647 (11)	1.27487 (9)	1.10477 (7)	0.0203 (2)
H1	0.6119	1.3115	1.0638	0.03*
O2	0.66614 (11)	1.31535 (9)	0.94318 (7)	0.0221 (2)
O3	0.31270 (10)	0.98499 (8)	0.81615 (6)	0.0183 (2)
O5	0.08963 (10)	0.91597 (8)	1.13482 (6)	0.0175 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0144 (5)	0.0145 (6)	0.0184 (7)	0.0044 (5)	0.0002 (5)	0.0005 (5)
C2	0.0146 (5)	0.0159 (6)	0.0166 (6)	0.0053 (5)	0.0023 (5)	0.0019 (5)
C3	0.0151 (5)	0.0172 (6)	0.0144 (6)	0.0069 (5)	0.0015 (5)	0.0017 (5)
C4	0.0146 (5)	0.0152 (6)	0.0174 (7)	0.0042 (5)	0.0006 (5)	0.0002 (5)
C5	0.0136 (5)	0.0171 (6)	0.0166 (7)	0.0059 (5)	0.0029 (5)	0.0043 (5)
C6	0.0164 (6)	0.0161 (6)	0.0147 (6)	0.0065 (5)	0.0010 (5)	0.0017 (5)
C22	0.0159 (6)	0.0158 (6)	0.0207 (7)	0.0062 (5)	0.0026 (5)	0.0034 (5)
C23	0.0237 (6)	0.0194 (6)	0.0206 (7)	0.0026 (5)	0.0074 (5)	0.0034 (5)
C31	0.0176 (6)	0.0210 (6)	0.0161 (7)	0.0004 (5)	−0.0009 (5)	−0.0019 (5)
C32	0.0279 (7)	0.0228 (7)	0.0239 (8)	0.0055 (6)	−0.0016 (6)	−0.0016 (6)
C33	0.0367 (8)	0.0356 (9)	0.0286 (9)	0.0099 (7)	0.0021 (7)	−0.0130 (7)
C34	0.0515 (10)	0.0480 (10)	0.0176 (8)	−0.0010 (8)	0.0087 (7)	−0.0076 (7)
C35	0.0760 (13)	0.0357 (9)	0.0200 (8)	0.0061 (9)	0.0027 (8)	0.0075 (7)
C36	0.0527 (10)	0.0259 (8)	0.0208 (8)	0.0129 (7)	−0.0005 (7)	0.0005 (6)
C37	0.0188 (6)	0.0218 (7)	0.0182 (7)	−0.0010 (5)	0.0005 (5)	−0.0022 (5)
C51	0.0160 (6)	0.0157 (6)	0.0203 (7)	0.0067 (5)	0.0034 (5)	0.0039 (5)
C52	0.0211 (6)	0.0182 (6)	0.0238 (7)	0.0041 (5)	0.0016 (5)	0.0014 (5)
C53	0.0220 (6)	0.0177 (6)	0.0345 (8)	0.0022 (5)	0.0061 (6)	0.0054 (6)
C54	0.0285 (7)	0.0213 (7)	0.0284 (8)	0.0088 (6)	0.0137 (6)	0.0109 (6)
C55	0.0317 (7)	0.0227 (7)	0.0196 (7)	0.0082 (6)	0.0066 (6)	0.0039 (6)
C56	0.0227 (6)	0.0188 (6)	0.0205 (7)	0.0028 (5)	0.0039 (5)	0.0032 (5)
C57	0.0157 (6)	0.0156 (6)	0.0174 (7)	0.0017 (5)	0.0016 (5)	0.0001 (5)
C61	0.0153 (6)	0.0157 (6)	0.0180 (7)	0.0001 (5)	0.0022 (5)	0.0000 (5)
C62	0.0291 (7)	0.0227 (7)	0.0190 (7)	0.0058 (6)	0.0029 (5)	0.0021 (5)
C63	0.0416 (8)	0.0260 (7)	0.0230 (8)	0.0094 (6)	0.0105 (6)	−0.0022 (6)
C64	0.0322 (8)	0.0185 (7)	0.0355 (9)	0.0078 (6)	0.0120 (6)	0.0006 (6)
C65	0.0229 (7)	0.0189 (7)	0.0300 (8)	0.0041 (5)	0.0036 (6)	0.0055 (6)
C66	0.0188 (6)	0.0199 (6)	0.0181 (7)	0.0025 (5)	0.0030 (5)	0.0011 (5)
C67	0.0196 (6)	0.0181 (6)	0.0157 (7)	0.0044 (5)	0.0010 (5)	0.0013 (5)
O1	0.0191 (4)	0.0186 (5)	0.0192 (5)	−0.0016 (3)	0.0028 (4)	−0.0012 (4)
O2	0.0206 (5)	0.0203 (5)	0.0223 (5)	−0.0003 (4)	0.0031 (4)	0.0018 (4)
O3	0.0182 (4)	0.0204 (5)	0.0131 (5)	0.0000 (3)	0.0027 (3)	−0.0016 (4)
O5	0.0176 (4)	0.0169 (4)	0.0157 (5)	−0.0001 (3)	0.0033 (3)	0.0016 (3)

C1—O1	1.3462 (14)	C37—H37B	0.99
C1—C6	1.3966 (17)	C51—C56	1.3852 (18)
C1—C2	1.4202 (17)	C51—C52	1.3962 (17)
C2—C3	1.4228 (16)	C51—C57	1.5064 (17)
C2—C22	1.4660 (17)	C52—C53	1.3870 (19)
C3—O3	1.3551 (15)	C52—H52	0.95
C3—C4	1.3867 (17)	C53—C54	1.384 (2)
C4—C5	1.3931 (17)	C53—H53	0.95
C4—H4	0.95	C54—C55	1.3843 (19)
C5—O5	1.3661 (14)	C54—H54	0.95
C5—C6	1.3970 (16)	C55—C56	1.3938 (18)
C6—C67	1.5046 (17)	C55—H55	0.95
C22—O2	1.2499 (15)	C56—H56	0.95
C22—C23	1.4983 (18)	C57—O5	1.4339 (14)
C23—H23A	0.98	C57—H57A	0.99
C23—H23B	0.98	C57—H57B	0.99
C23—H23C	0.98	C61—C66	1.3885 (18)
C31—C32	1.3829 (19)	C61—C62	1.3933 (18)
C31—C36	1.384 (2)	C61—C67	1.5217 (18)
C31—C37	1.4997 (18)	C62—C63	1.3846 (19)
C32—C33	1.384 (2)	C62—H62	0.95
C32—H32	0.95	C63—C64	1.383 (2)
C33—C34	1.375 (2)	C63—H63	0.95
C33—H33	0.95	C64—C65	1.380 (2)
C34—C35	1.380 (2)	C64—H64	0.95
C34—H34	0.95	C65—C66	1.3920 (19)
C35—C36	1.382 (2)	C65—H65	0.95
C35—H35	0.95	C66—H66	0.95
C36—H36	0.95	C67—H67A	0.99
C37—O3	1.4454 (14)	C67—H67B	0.99
C37—H37A	0.99	O1—H1	0.84
O1—C1—C6	115.78 (11)	C56—C51—C52	118.79 (12)
O1—C1—C2	120.94 (11)	C56—C51—C57	122.41 (11)
C6—C1—C2	123.28 (11)	C52—C51—C57	118.80 (11)
C1—C2—C3	116.48 (11)	C53—C52—C51	120.78 (13)
C1—C2—C22	118.76 (11)	C53—C52—H52	119.6
C3—C2—C22	124.76 (11)	C51—C52—H52	119.6
O3—C3—C4	122.45 (11)	C54—C53—C52	119.87 (12)
O3—C3—C2	116.19 (10)	C54—C53—H53	120.1
C4—C3—C2	121.34 (11)	C52—C53—H53	120.1
C3—C4—C5	119.44 (11)	C53—C54—C55	119.98 (12)
C3—C4—H4	120.3	C53—C54—H54	120
C5—C4—H4	120.3	C55—C54—H54	120
O5—C5—C4	122.82 (11)	C54—C55—C56	120.00 (13)
O5—C5—C6	114.76 (11)	C54—C55—H55	120
C4—C5—C6	122.40 (11)	C56—C55—H55	120
C1—C6—C5	117.01 (11)	C51—C56—C55	120.58 (12)
C1—C6—C67	119.98 (11)	C51—C56—H56	119.7
C5—C6—C67	122.97 (11)	C55—C56—H56	119.7
O2—C22—C2	119.75 (11)	O5—C57—C51	108.42 (10)
O2—C22—C23	116.79 (11)	O5—C57—H57A	110
C2—C22—C23	123.46 (11)	C51—C57—H57A	110
C22—C23—H23A	109.5	O5—C57—H57B	110
C22—C23—H23B	109.5	C51—C57—H57B	110
H23A—C23—H23B	109.5	H57A—C57—H57B	108.4
C22—C23—H23C	109.5	C66—C61—C62	117.80 (12)
H23A—C23—H23C	109.5	C66—C61—C67	123.21 (11)
H23B—C23—H23C	109.5	C62—C61—C67	118.99 (12)
C32—C31—C36	118.94 (13)	C63—C62—C61	121.13 (13)
C32—C31—C37	120.53 (12)	C63—C62—H62	119.4
C36—C31—C37	120.53 (12)	C61—C62—H62	119.4
C31—C32—C33	120.51 (14)	C64—C63—C62	120.33 (13)
C31—C32—H32	119.7	C64—C63—H63	119.8
C33—C32—H32	119.7	C62—C63—H63	119.8
C34—C33—C32	120.27 (15)	C65—C64—C63	119.43 (13)
C34—C33—H33	119.9	C65—C64—H64	120.3
C32—C33—H33	119.9	C63—C64—H64	120.3
C33—C34—C35	119.57 (15)	C64—C65—C66	120.09 (13)
C33—C34—H34	120.2	C64—C65—H65	120
C35—C34—H34	120.2	C66—C65—H65	120
C34—C35—C36	120.26 (16)	C61—C66—C65	121.21 (12)
C34—C35—H35	119.9	C61—C66—H66	119.4
C36—C35—H35	119.9	C65—C66—H66	119.4
C35—C36—C31	120.44 (15)	C6—C67—C61	116.24 (11)
C35—C36—H36	119.8	C6—C67—H67A	108.2
C31—C36—H36	119.8	C61—C67—H67A	108.2
O3—C37—C31	106.67 (10)	C6—C67—H67B	108.2
O3—C37—H37A	110.4	C61—C67—H67B	108.2
C31—C37—H37A	110.4	H67A—C67—H67B	107.4
O3—C37—H37B	110.4	C1—O1—H1	109.5
C31—C37—H37B	110.4	C3—O3—C37	118.66 (9)
H37A—C37—H37B	108.6	C5—O5—C57	118.65 (9)
O1—C1—C2—C3	178.13 (11)	C37—C31—C36—C35	178.08 (14)
C6—C1—C2—C3	−1.90 (18)	C32—C31—C37—O3	114.05 (13)
O1—C1—C2—C22	−1.70 (17)	C36—C31—C37—O3	−65.12 (16)
C6—C1—C2—C22	178.27 (11)	C56—C51—C52—C53	0.88 (19)
C1—C2—C3—O3	−178.13 (10)	C57—C51—C52—C53	179.95 (12)
C22—C2—C3—O3	1.69 (18)	C51—C52—C53—C54	−0.1 (2)
C1—C2—C3—C4	0.70 (17)	C52—C53—C54—C55	−0.9 (2)
C22—C2—C3—C4	−179.48 (12)	C53—C54—C55—C56	1.0 (2)
O3—C3—C4—C5	178.61 (11)	C52—C51—C56—C55	−0.74 (19)
C2—C3—C4—C5	−0.14 (18)	C57—C51—C56—C55	−179.78 (12)
C3—C4—C5—O5	−178.20 (11)	C54—C55—C56—C51	−0.2 (2)
C3—C4—C5—C6	0.70 (18)	C56—C51—C57—O5	−14.90 (16)
O1—C1—C6—C5	−177.61 (11)	C52—C51—C57—O5	166.07 (11)
C2—C1—C6—C5	2.42 (18)	C66—C61—C62—C63	1.32 (19)
O1—C1—C6—C67	0.22 (17)	C67—C61—C62—C63	−178.38 (13)
C2—C1—C6—C67	−179.75 (11)	C61—C62—C63—C64	−0.7 (2)
O5—C5—C6—C1	177.20 (10)	C62—C63—C64—C65	−0.2 (2)
C4—C5—C6—C1	−1.78 (18)	C63—C64—C65—C66	0.5 (2)
O5—C5—C6—C67	−0.56 (17)	C62—C61—C66—C65	−1.04 (18)
C4—C5—C6—C67	−179.54 (11)	C67—C61—C66—C65	178.65 (12)
C1—C2—C22—O2	2.78 (18)	C64—C65—C66—C61	0.2 (2)
C3—C2—C22—O2	−177.04 (12)	C1—C6—C67—C61	76.07 (15)
C1—C2—C22—C23	−177.02 (12)	C5—C6—C67—C61	−106.24 (14)
C3—C2—C22—C23	3.16 (19)	C66—C61—C67—C6	−7.73 (17)
C36—C31—C32—C33	0.8 (2)	C62—C61—C67—C6	171.96 (11)
C37—C31—C32—C33	−178.39 (13)	C4—C3—O3—C37	5.21 (17)
C31—C32—C33—C34	0.1 (2)	C2—C3—O3—C37	−175.98 (11)
C32—C33—C34—C35	−0.7 (3)	C31—C37—O3—C3	−177.49 (10)
C33—C34—C35—C36	0.4 (3)	C4—C5—O5—C57	6.31 (17)
C34—C35—C36—C31	0.5 (3)	C6—C5—O5—C57	−172.67 (10)
C32—C31—C36—C35	−1.1 (2)	C51—C57—O5—C5	174.63 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C56—H56···O5	0.95	2.39	2.7282 (15)	101
C67—H67B···O5	0.99	2.34	2.7882 (15)	106
O1—H1···O2	0.84	1.72	2.4744 (13)	148
C57—H57A···O2i	0.99	2.58	3.4592 (16)	148
C23—H23B···Cg3ii	0.98	2.83	3.6790 (16)	145
C57—H57B···Cg1ii	0.99	2.64	3.5106 (14)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the C1–C6 and C31–C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C56—H56⋯O5	0.95	2.39	2.7282 (15)	101
C67—H67B⋯O5	0.99	2.34	2.7882 (15)	106
O1—H1⋯O2	0.84	1.72	2.4744 (13)	148
C57—H57A⋯O2i	0.99	2.58	3.4592 (16)	148
C23—H23B⋯Cg3ii	0.98	2.83	3.6790 (16)	145
C57—H57B⋯Cg1ii	0.99	2.64	3.5106 (14)	146

Symmetry codes: (i) ; (ii) .