2,2'-Dimethyl-5,5'-dipropan-2-yl-4,4'-(phenyl-methyl-ene)diphenol.

In the title mol-ecule, C(27)H(32)O(2), the aromatic rings are in a propeller configuration. In the crystal, mol-ecules are linked through O-H⋯O hydrogen bonds forming a two-dimensional network which develops parallel to (010). Futhermore, weak C-H⋯π inter-actions involving the two substituted rings build up a three-dimensional network.

Related literature

R-(−)-Carvone, p-mentha-6,8-dien-2-on, is the major constituent of spearmint essential oil of Menthe spicata (Gershenzon et al., 1989 ▶) and is an important chiron for the synthesis of complex natural products (Wang et al., 2001 ▶) and anti­viral agents. We have reported an efficient method which affords direct access to p-cymene derivatives from R-(−)-carvone, see: Majidi & Fihi (2004 ▶). For our inter­est in the development of strategies for the synthesis of natural product derivatives, see: Majidi et al., 2005 ▶). For related structures, see; Guo et al. (2005 ▶); Sarma & Baruah (2004 ▶, 2005 ▶); Veldman et al. (1996 ▶); Yang et al. (2005 ▶).

Experimental

Crystal data

C27H32O2

M = 388.53

Monoclinic,

a = 11.3775 (7) Å

b = 24.6369 (11) Å

c = 8.8687 (6) Å

β = 112.913 (8)°

V = 2289.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 180 K

0.55 × 0.35 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.723, T max = 1.000

10216 measured reflections

2838 independent reflections

1792 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.103

S = 0.95

2838 reflections

269 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global, azrour7. DOI: 10.1107/S1600536810033441/pv2319sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033441/pv2319Isup2.hkl

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

C27H32O2	F(000) = 840
Mr = 388.53	Dx = 1.127 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1555 reflections
a = 11.3775 (7) Å	θ = 2.6–32.0°
b = 24.6369 (11) Å	µ = 0.07 mm−1
c = 8.8687 (6) Å	T = 180 K
β = 112.913 (8)°	Plate, colourless
V = 2289.8 (2) Å3	0.55 × 0.35 × 0.11 mm
Z = 4

Oxford Diffraction Xcalibur diffractometer	2838 independent reflections
Radiation source: fine-focus sealed tube	1792 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 8.2632 pixels mm-1	θmax = 28.3°, θmin = 2.6°
ω and φ scans	h = −15→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −32→32
Tmin = 0.723, Tmax = 1.000	l = −8→11
10216 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.103	w = 1/[σ2(Fo2) + (0.0562P)2] where P = (Fo2 + 2Fc2)/3
S = 0.95	(Δ/σ)max = 0.007
2838 reflections	Δρmax = 0.32 e Å−3
269 parameters	Δρmin = −0.36 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0197 (15)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm, CrysAlis RED (Oxford Diffraction, 2006).

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
C1	0.3749 (2)	0.33943 (10)	0.0751 (3)	0.0236 (6)
H1	0.3948	0.3372	0.1951	0.028*
C11	0.3659 (3)	0.28073 (10)	0.0172 (4)	0.0282 (6)
C12	0.2878 (3)	0.26471 (12)	−0.1384 (4)	0.0457 (9)
H12	0.2378	0.2910	−0.2151	0.055*
C13	0.2813 (4)	0.21076 (15)	−0.1844 (6)	0.0651 (12)
H13	0.2276	0.2003	−0.2925	0.078*
C14	0.3516 (4)	0.17237 (14)	−0.0751 (6)	0.0681 (12)
H14	0.3459	0.1353	−0.1063	0.082*
C15	0.4296 (4)	0.18779 (13)	0.0784 (6)	0.0636 (11)
H15	0.4795	0.1614	0.1544	0.076*
C16	0.4370 (3)	0.24118 (12)	0.1246 (4)	0.0460 (8)
H16	0.4920	0.2512	0.2325	0.055*
C21	0.2487 (3)	0.36963 (10)	0.0021 (3)	0.0256 (6)
C22	0.1565 (3)	0.36542 (11)	0.0696 (3)	0.0286 (7)
C23	0.0465 (3)	0.39639 (11)	0.0018 (3)	0.0287 (7)
H23	−0.0163	0.3942	0.0474	0.034*
C24	0.0257 (2)	0.43028 (10)	−0.1300 (3)	0.0252 (6)
C25	0.1125 (3)	0.43357 (10)	−0.2028 (3)	0.0258 (6)
C26	0.2232 (3)	0.40303 (10)	−0.1329 (3)	0.0248 (6)
H26	0.2850	0.4051	−0.1802	0.030*
C31	0.4858 (2)	0.37081 (10)	0.0609 (3)	0.0242 (6)
C32	0.5345 (2)	0.41658 (10)	0.1601 (3)	0.0247 (6)
C33	0.6394 (2)	0.44281 (11)	0.1522 (3)	0.0252 (6)
H33	0.6734	0.4736	0.2197	0.030*
C34	0.6959 (2)	0.42541 (11)	0.0491 (3)	0.0261 (6)
C35	0.6492 (2)	0.38059 (11)	−0.0521 (3)	0.0265 (6)
C36	0.5436 (2)	0.35466 (11)	−0.0424 (3)	0.0244 (6)
H36	0.5095	0.3241	−0.1108	0.029*
C221	0.1706 (3)	0.32907 (14)	0.2133 (4)	0.0450 (8)
H221	0.2512	0.3078	0.2409	0.054*
C222	0.1828 (5)	0.36190 (19)	0.3634 (5)	0.0802 (14)
H22A	0.2517	0.3885	0.3867	0.120*
H22B	0.2022	0.3375	0.4574	0.120*
H22C	0.1023	0.3809	0.3431	0.120*
C223	0.0613 (4)	0.28885 (15)	0.1724 (5)	0.0693 (12)
H22D	0.0777	0.2642	0.2652	0.104*
H22E	0.0543	0.2678	0.0754	0.104*
H22F	−0.0185	0.3086	0.1503	0.104*
C251	0.0870 (3)	0.46852 (13)	−0.3500 (4)	0.0427 (8)
H25A	0.0060	0.4577	−0.4368	0.064*
H25B	0.1563	0.4642	−0.3886	0.064*
H25C	0.0819	0.5066	−0.3210	0.064*
C321	0.4791 (3)	0.43655 (11)	0.2792 (3)	0.0307 (7)
H321	0.3979	0.4162	0.2566	0.037*
C322	0.5693 (3)	0.42314 (13)	0.4530 (4)	0.0475 (9)
H32A	0.5845	0.3839	0.4631	0.071*
H32B	0.5312	0.4347	0.5296	0.071*
H32C	0.6505	0.4421	0.4783	0.071*
C323	0.4463 (3)	0.49670 (11)	0.2585 (4)	0.0391 (7)
H32D	0.5242	0.5178	0.2798	0.059*
H32E	0.4083	0.5075	0.3360	0.059*
H32F	0.3854	0.5036	0.1465	0.059*
C351	0.7107 (3)	0.35959 (12)	−0.1625 (4)	0.0357 (7)
H35A	0.7287	0.3900	−0.2216	0.054*
H35B	0.6530	0.3339	−0.2412	0.054*
H35C	0.7907	0.3411	−0.0969	0.054*
O24	−0.08390 (16)	0.46191 (7)	−0.1939 (2)	0.0328 (5)
H24	−0.1295	0.4564	−0.1403	0.049*
O34	0.80030 (17)	0.45253 (7)	0.0405 (2)	0.0346 (5)
H34	0.8113	0.4819	0.0922	0.052*

	U11	U22	U33	U12	U13	U23
C1	0.0212 (14)	0.0255 (14)	0.0257 (15)	0.0017 (11)	0.0109 (12)	0.0019 (11)
C11	0.0210 (13)	0.0262 (14)	0.0406 (17)	−0.0019 (11)	0.0154 (13)	0.0019 (13)
C12	0.0331 (17)	0.0398 (19)	0.054 (2)	0.0041 (14)	0.0065 (15)	−0.0117 (16)
C13	0.0379 (19)	0.058 (2)	0.089 (3)	−0.0044 (18)	0.013 (2)	−0.038 (2)
C14	0.059 (2)	0.0273 (18)	0.132 (4)	−0.0099 (18)	0.052 (3)	−0.021 (2)
C15	0.073 (3)	0.0267 (18)	0.099 (3)	0.0060 (18)	0.041 (3)	0.010 (2)
C16	0.050 (2)	0.0331 (17)	0.057 (2)	0.0036 (15)	0.0232 (17)	0.0079 (16)
C21	0.0251 (14)	0.0213 (13)	0.0322 (16)	−0.0013 (11)	0.0131 (13)	−0.0015 (12)
C22	0.0257 (15)	0.0297 (16)	0.0341 (17)	0.0005 (12)	0.0154 (14)	0.0022 (13)
C23	0.0241 (15)	0.0315 (15)	0.0356 (17)	0.0016 (12)	0.0173 (13)	0.0015 (13)
C24	0.0165 (13)	0.0247 (14)	0.0325 (16)	0.0010 (11)	0.0074 (12)	−0.0016 (13)
C25	0.0255 (14)	0.0239 (14)	0.0291 (15)	−0.0013 (11)	0.0120 (12)	0.0020 (12)
C26	0.0232 (14)	0.0256 (14)	0.0286 (16)	−0.0004 (11)	0.0133 (12)	0.0019 (12)
C31	0.0202 (13)	0.0240 (14)	0.0289 (16)	0.0015 (11)	0.0100 (12)	0.0029 (12)
C32	0.0227 (14)	0.0255 (14)	0.0262 (15)	0.0017 (11)	0.0097 (12)	0.0014 (12)
C33	0.0197 (13)	0.0247 (13)	0.0301 (16)	−0.0014 (11)	0.0083 (12)	−0.0039 (12)
C34	0.0184 (14)	0.0294 (15)	0.0312 (16)	0.0028 (11)	0.0104 (12)	0.0066 (12)
C35	0.0248 (15)	0.0286 (15)	0.0285 (16)	0.0053 (12)	0.0128 (13)	0.0032 (13)
C36	0.0220 (14)	0.0245 (14)	0.0259 (15)	−0.0001 (11)	0.0084 (12)	−0.0012 (12)
C221	0.0374 (19)	0.056 (2)	0.052 (2)	0.0172 (16)	0.0280 (16)	0.0237 (18)
C222	0.097 (3)	0.105 (4)	0.045 (3)	−0.021 (3)	0.034 (2)	0.013 (2)
C223	0.083 (3)	0.049 (2)	0.087 (3)	−0.004 (2)	0.046 (2)	0.026 (2)
C251	0.0353 (17)	0.051 (2)	0.045 (2)	0.0133 (15)	0.0193 (15)	0.0196 (16)
C321	0.0289 (16)	0.0335 (16)	0.0344 (18)	−0.0023 (12)	0.0174 (14)	−0.0064 (13)
C322	0.064 (2)	0.048 (2)	0.0372 (19)	0.0086 (17)	0.0274 (17)	−0.0017 (16)
C323	0.0398 (17)	0.0411 (17)	0.0404 (19)	0.0043 (14)	0.0201 (14)	−0.0082 (15)
C351	0.0346 (17)	0.0420 (18)	0.0348 (18)	−0.0014 (14)	0.0181 (14)	−0.0056 (14)
O24	0.0235 (11)	0.0363 (11)	0.0433 (13)	0.0058 (9)	0.0183 (9)	0.0051 (9)
O34	0.0268 (11)	0.0357 (10)	0.0472 (13)	−0.0063 (9)	0.0209 (10)	−0.0060 (10)

C1—C21	1.520 (4)	C34—C35	1.391 (4)
C1—C11	1.524 (4)	C34—O34	1.390 (3)
C1—C31	1.526 (4)	C35—C36	1.392 (4)
C1—H1	1.0000	C35—C351	1.501 (4)
C11—C12	1.377 (4)	C36—H36	0.9500
C11—C16	1.382 (4)	C221—C222	1.518 (5)
C12—C13	1.384 (4)	C221—C223	1.519 (5)
C12—H12	0.9500	C221—H221	1.0000
C13—C14	1.367 (6)	C222—H22A	0.9800
C13—H13	0.9500	C222—H22B	0.9800
C14—C15	1.359 (6)	C222—H22C	0.9800
C14—H14	0.9500	C223—H22D	0.9800
C15—C16	1.370 (5)	C223—H22E	0.9800
C15—H15	0.9500	C223—H22F	0.9800
C16—H16	0.9500	C251—H25A	0.9800
C21—C26	1.387 (4)	C251—H25B	0.9800
C21—C22	1.399 (4)	C251—H25C	0.9800
C22—C23	1.387 (4)	C321—C322	1.518 (4)
C22—C221	1.514 (4)	C321—C323	1.522 (4)
C23—C24	1.380 (4)	C321—H321	1.0000
C23—H23	0.9500	C322—H32A	0.9800
C24—C25	1.377 (4)	C322—H32B	0.9800
C24—O24	1.391 (3)	C322—H32C	0.9800
C25—C26	1.389 (4)	C323—H32D	0.9800
C25—C251	1.495 (4)	C323—H32E	0.9800
C26—H26	0.9500	C323—H32F	0.9800
C31—C36	1.377 (4)	C351—H35A	0.9800
C31—C32	1.404 (3)	C351—H35B	0.9800
C32—C33	1.383 (4)	C351—H35C	0.9800
C32—C321	1.508 (4)	O24—H24	0.8400
C33—C34	1.375 (4)	O34—H34	0.8400
C33—H33	0.9500
C21—C1—C11	113.1 (2)	C34—C35—C351	122.4 (2)
C21—C1—C31	113.04 (19)	C36—C35—C351	121.0 (2)
C11—C1—C31	113.8 (2)	C31—C36—C35	123.7 (2)
C21—C1—H1	105.3	C31—C36—H36	118.1
C11—C1—H1	105.3	C35—C36—H36	118.1
C31—C1—H1	105.3	C22—C221—C222	111.5 (3)
C12—C11—C16	117.7 (3)	C22—C221—C223	112.1 (3)
C12—C11—C1	122.8 (3)	C222—C221—C223	110.1 (3)
C16—C11—C1	119.5 (3)	C22—C221—H221	107.7
C11—C12—C13	120.7 (3)	C222—C221—H221	107.7
C11—C12—H12	119.7	C223—C221—H221	107.7
C13—C12—H12	119.7	C221—C222—H22A	109.5
C14—C13—C12	120.4 (4)	C221—C222—H22B	109.5
C14—C13—H13	119.8	H22A—C222—H22B	109.5
C12—C13—H13	119.8	C221—C222—H22C	109.5
C15—C14—C13	119.4 (3)	H22A—C222—H22C	109.5
C15—C14—H14	120.3	H22B—C222—H22C	109.5
C13—C14—H14	120.3	C221—C223—H22D	109.5
C14—C15—C16	120.5 (4)	C221—C223—H22E	109.5
C14—C15—H15	119.7	H22D—C223—H22E	109.5
C16—C15—H15	119.7	C221—C223—H22F	109.5
C15—C16—C11	121.3 (4)	H22D—C223—H22F	109.5
C15—C16—H16	119.4	H22E—C223—H22F	109.5
C11—C16—H16	119.4	C25—C251—H25A	109.5
C26—C21—C22	118.2 (2)	C25—C251—H25B	109.5
C26—C21—C1	120.2 (2)	H25A—C251—H25B	109.5
C22—C21—C1	121.5 (2)	C25—C251—H25C	109.5
C23—C22—C21	118.3 (2)	H25A—C251—H25C	109.5
C23—C22—C221	118.2 (3)	H25B—C251—H25C	109.5
C21—C22—C221	123.5 (2)	C32—C321—C322	109.7 (2)
C24—C23—C22	121.9 (3)	C32—C321—C323	112.5 (2)
C24—C23—H23	119.1	C322—C321—C323	111.8 (2)
C22—C23—H23	119.1	C32—C321—H321	107.5
C25—C24—C23	121.0 (2)	C322—C321—H321	107.5
C25—C24—O24	118.0 (2)	C323—C321—H321	107.5
C23—C24—O24	121.0 (2)	C321—C322—H32A	109.5
C24—C25—C26	116.7 (2)	C321—C322—H32B	109.5
C24—C25—C251	120.8 (2)	H32A—C322—H32B	109.5
C26—C25—C251	122.4 (3)	C321—C322—H32C	109.5
C25—C26—C21	123.7 (3)	H32A—C322—H32C	109.5
C25—C26—H26	118.1	H32B—C322—H32C	109.5
C21—C26—H26	118.1	C321—C323—H32D	109.5
C36—C31—C32	118.4 (2)	C321—C323—H32E	109.5
C36—C31—C1	122.1 (2)	H32D—C323—H32E	109.5
C32—C31—C1	119.5 (2)	C321—C323—H32F	109.5
C33—C32—C31	118.7 (2)	H32D—C323—H32F	109.5
C33—C32—C321	119.2 (2)	H32E—C323—H32F	109.5
C31—C32—C321	122.1 (2)	C35—C351—H35A	109.5
C34—C33—C32	121.6 (2)	C35—C351—H35B	109.5
C34—C33—H33	119.2	H35A—C351—H35B	109.5
C32—C33—H33	119.2	C35—C351—H35C	109.5
C33—C34—C35	121.1 (2)	H35A—C351—H35C	109.5
C33—C34—O34	121.1 (2)	H35B—C351—H35C	109.5
C35—C34—O34	117.8 (2)	C24—O24—H24	109.5
C34—C35—C36	116.5 (2)	C34—O34—H34	109.5

Cg2 and Cg3 are the centroids of the C21–C26 and C31–C36 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24···O34i	0.84	2.05	2.871 (3)	164
O34—H34···O24ii	0.84	2.27	3.051 (3)	154
C23—H23···O34i	0.95	2.51	3.259 (3)	135
C13—H13···Cg3iii	0.95	2.92	3.658 (4)	135
C15—H15···Cg2iv	0.95	2.86	3.790 (5)	167

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C21–C26 and C31–C36 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O24—H24⋯O34i	0.84	2.05	2.871 (3)	164
O34—H34⋯O24ii	0.84	2.27	3.051 (3)	154
C23—H23⋯O34i	0.95	2.51	3.259 (3)	135
C13—H13⋯Cg3iii	0.95	2.92	3.658 (4)	135
C15—H15⋯Cg2iv	0.95	2.86	3.790 (5)	167

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