2,2'-[(1E)-3-Phenyl-prop-2-ene-1,1-di-yl]bis-(3-hy-droxy-5,5-dimethyl-cyclo-hex-2-en-1-one).

In the title mol-ecule, C(25)H(30)O(4), the two cyclo-hexene rings adopt envelope conformations. The two hy-droxy groups are involved in the formation of intra-molecular O-H⋯O hydrogen bonds. In the crystal structure, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules related by translation along the axis a into chains.

Related literature

For related structures, see: Bolte et al. (2001 ▶); Palakshi Reddy et al. (2010 ▶); Shi et al. (1998 ▶). For applications of related compounds, see: Ali et al. (2011 ▶); Wang et al. (2006 ▶). For the synthesis of related compounds, see: Ramachary & Mamillapalli (2007 ▶); Rohr & Mahrwald (2009 ▶).

Experimental

Crystal data

C25H30O4

M = 394.49

Triclinic,

a = 5.9465 (15) Å

b = 11.214 (3) Å

c = 17.170 (4) Å

α = 82.804 (3)°

β = 81.062 (3)°

γ = 76.927 (3)°

V = 1096.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.28 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.977, T max = 0.984

11804 measured reflections

4149 independent reflections

3560 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.154

S = 1.02

4149 reflections

269 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811033745/cv5137sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033745/cv5137Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033745/cv5137Isup3.cml

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

C25H30O4	Z = 2
Mr = 394.49	F(000) = 424
Triclinic, P1	Dx = 1.194 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9465 (15) Å	Cell parameters from 2118 reflections
b = 11.214 (3) Å	θ = 2.3–27.2°
c = 17.170 (4) Å	µ = 0.08 mm−1
α = 82.804 (3)°	T = 293 K
β = 81.062 (3)°	Block, colourless
γ = 76.927 (3)°	0.30 × 0.28 × 0.20 mm
V = 1096.9 (5) Å3

Bruker APEXII area-detector diffractometer	4149 independent reflections
Radiation source: fine-focus sealed tube	3560 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −7→6
Tmin = 0.977, Tmax = 0.984	k = −13→13
11804 measured reflections	l = −21→9

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)] = 0.071	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.019P)2 + 1.9414P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4149 reflections	Δρmax = 0.29 e Å−3
269 parameters	Δρmin = −0.20 e Å−3
0 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: 0.0130 (19)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C6	0.2857 (5)	0.8045 (2)	0.81379 (16)	0.0357 (6)
C5	0.4316 (5)	0.7081 (2)	0.85206 (16)	0.0374 (6)
C1	0.0541 (5)	0.8394 (3)	0.85021 (17)	0.0429 (7)
C4	0.3647 (6)	0.6518 (3)	0.93287 (17)	0.0506 (8)
H4A	0.5010	0.6299	0.9604	0.061*
H4B	0.3156	0.5764	0.9283	0.061*
C2	−0.0248 (6)	0.7860 (3)	0.93157 (19)	0.0576 (9)
H2A	−0.1034	0.7208	0.9267	0.069*
H2B	−0.1377	0.8494	0.9586	0.069*
C3	0.1700 (6)	0.7341 (3)	0.98281 (17)	0.0514 (8)
C7	0.2611 (8)	0.8383 (4)	1.0080 (2)	0.0740 (11)
H7A	0.3860	0.8043	1.0389	0.111*
H7B	0.1375	0.8896	1.0392	0.111*
H7C	0.3169	0.8863	0.9619	0.111*
C8	0.0803 (8)	0.6583 (4)	1.0562 (2)	0.0821 (13)
H8A	0.0167	0.5950	1.0405	0.123*
H8B	−0.0386	0.7107	1.0883	0.123*
H8C	0.2064	0.6215	1.0861	0.123*
C9	0.3718 (4)	0.8650 (2)	0.73423 (15)	0.0342 (6)
H9	0.5418	0.8459	0.7315	0.041*
C20	0.3317 (5)	1.2099 (2)	0.75974 (16)	0.0379 (6)
C18	0.3039 (5)	1.0046 (2)	0.72762 (16)	0.0398 (6)
H18	0.1955	1.0426	0.6938	0.048*
C19	0.3858 (5)	1.0746 (2)	0.76568 (18)	0.0427 (7)
H19	0.4901	1.0350	0.8005	0.051*
C21	0.1371 (5)	1.2795 (3)	0.72830 (18)	0.0458 (7)
H21	0.0347	1.2401	0.7110	0.055*
C25	0.4806 (6)	1.2720 (3)	0.78509 (18)	0.0482 (7)
H25	0.6132	1.2275	0.8060	0.058*
C23	0.2417 (7)	1.4659 (3)	0.7482 (2)	0.0605 (9)
H23	0.2115	1.5514	0.7444	0.073*
C24	0.4348 (7)	1.3986 (3)	0.7797 (2)	0.0593 (9)
H24	0.5354	1.4387	0.7975	0.071*
C22	0.0926 (6)	1.4064 (3)	0.7221 (2)	0.0573 (9)
H22	−0.0381	1.4516	0.7004	0.069*
C10	0.3235 (5)	0.8101 (2)	0.66340 (15)	0.0355 (6)
C11	0.4927 (5)	0.7122 (2)	0.63160 (16)	0.0395 (6)
C15	0.1190 (5)	0.8469 (3)	0.62977 (16)	0.0404 (6)
C12	0.4642 (6)	0.6603 (3)	0.55792 (18)	0.0521 (8)
H12A	0.3949	0.5890	0.5732	0.063*
H12B	0.6169	0.6329	0.5288	0.063*
C13	0.3140 (6)	0.7512 (3)	0.50335 (17)	0.0494 (7)
C14	0.0882 (5)	0.8041 (3)	0.55416 (18)	0.0523 (8)
H14A	0.0015	0.8728	0.5234	0.063*
H14B	−0.0049	0.7418	0.5664	0.063*
C16	0.4406 (7)	0.8516 (3)	0.4663 (2)	0.0679 (10)
H16A	0.3454	0.9085	0.4320	0.102*
H16B	0.5847	0.8157	0.4362	0.102*
H16C	0.4721	0.8941	0.5072	0.102*
C17	0.2593 (8)	0.6843 (4)	0.4381 (2)	0.0787 (12)
H17A	0.1771	0.6215	0.4618	0.118*
H17B	0.4020	0.6474	0.4077	0.118*
H17C	0.1646	0.7421	0.4040	0.118*
O3	0.6399 (3)	0.65715 (19)	0.81993 (12)	0.0469 (5)
H3	0.6525	0.6755	0.7719	0.070*
O1	0.6739 (4)	0.66073 (19)	0.66454 (12)	0.0501 (5)
O2	−0.0650 (4)	0.9210 (2)	0.66144 (13)	0.0554 (6)
H2	−0.0526	0.9260	0.7078	0.083*
O4	−0.1002 (4)	0.9153 (2)	0.81522 (13)	0.0588 (6)

	U11	U22	U33	U12	U13	U23
C6	0.0404 (14)	0.0296 (13)	0.0385 (14)	−0.0068 (11)	−0.0109 (11)	−0.0022 (10)
C5	0.0417 (15)	0.0331 (13)	0.0377 (14)	−0.0070 (11)	−0.0087 (11)	−0.0025 (11)
C1	0.0365 (15)	0.0466 (16)	0.0442 (16)	−0.0036 (12)	−0.0084 (12)	−0.0052 (13)
C4	0.063 (2)	0.0411 (16)	0.0410 (16)	−0.0011 (14)	−0.0069 (14)	0.0042 (13)
C2	0.0456 (18)	0.076 (2)	0.0470 (18)	−0.0086 (16)	−0.0009 (14)	−0.0033 (16)
C3	0.0582 (19)	0.0573 (19)	0.0348 (15)	−0.0079 (15)	−0.0048 (13)	0.0016 (13)
C7	0.090 (3)	0.076 (3)	0.058 (2)	−0.006 (2)	−0.020 (2)	−0.0202 (19)
C8	0.094 (3)	0.092 (3)	0.046 (2)	−0.009 (2)	0.003 (2)	0.008 (2)
C9	0.0320 (13)	0.0282 (12)	0.0403 (14)	−0.0028 (10)	−0.0063 (11)	0.0007 (10)
C20	0.0396 (14)	0.0348 (14)	0.0373 (14)	−0.0053 (11)	−0.0014 (11)	−0.0055 (11)
C18	0.0470 (16)	0.0309 (13)	0.0404 (15)	−0.0041 (12)	−0.0124 (12)	0.0014 (11)
C19	0.0408 (15)	0.0347 (14)	0.0519 (17)	0.0003 (12)	−0.0159 (13)	−0.0048 (12)
C21	0.0474 (17)	0.0377 (15)	0.0522 (17)	−0.0039 (13)	−0.0116 (13)	−0.0069 (13)
C25	0.0503 (17)	0.0484 (17)	0.0492 (17)	−0.0129 (14)	−0.0095 (14)	−0.0087 (14)
C23	0.082 (3)	0.0341 (16)	0.063 (2)	−0.0151 (17)	0.0035 (18)	−0.0068 (15)
C24	0.070 (2)	0.0486 (18)	0.066 (2)	−0.0238 (17)	−0.0063 (18)	−0.0157 (16)
C22	0.064 (2)	0.0383 (16)	0.062 (2)	0.0031 (15)	−0.0098 (17)	0.0021 (14)
C10	0.0381 (14)	0.0300 (13)	0.0369 (14)	−0.0073 (11)	−0.0034 (11)	0.0013 (10)
C11	0.0435 (15)	0.0321 (13)	0.0374 (14)	−0.0052 (12)	0.0009 (12)	0.0043 (11)
C15	0.0406 (15)	0.0373 (14)	0.0420 (15)	−0.0073 (12)	−0.0036 (12)	−0.0031 (12)
C12	0.069 (2)	0.0375 (15)	0.0447 (17)	−0.0006 (14)	−0.0048 (15)	−0.0065 (13)
C13	0.063 (2)	0.0474 (17)	0.0367 (15)	−0.0073 (15)	−0.0066 (14)	−0.0069 (13)
C14	0.0488 (18)	0.061 (2)	0.0493 (18)	−0.0090 (15)	−0.0148 (14)	−0.0093 (15)
C16	0.082 (3)	0.063 (2)	0.049 (2)	−0.0109 (19)	−0.0005 (18)	0.0112 (16)
C17	0.106 (3)	0.076 (3)	0.055 (2)	−0.002 (2)	−0.024 (2)	−0.0255 (19)
O3	0.0456 (12)	0.0445 (11)	0.0429 (11)	0.0047 (9)	−0.0072 (9)	0.0005 (9)
O1	0.0460 (12)	0.0466 (12)	0.0470 (12)	0.0077 (9)	−0.0030 (9)	−0.0001 (9)
O2	0.0422 (12)	0.0646 (14)	0.0536 (13)	0.0089 (10)	−0.0110 (10)	−0.0155 (11)
O4	0.0404 (12)	0.0707 (15)	0.0545 (13)	0.0098 (11)	−0.0093 (10)	−0.0009 (11)

C6—C5	1.388 (4)	C21—H21	0.9300
C6—C1	1.411 (4)	C25—C24	1.378 (4)
C6—C9	1.515 (4)	C25—H25	0.9300
C5—O3	1.308 (3)	C23—C24	1.371 (5)
C5—C4	1.485 (4)	C23—C22	1.377 (5)
C1—O4	1.272 (3)	C23—H23	0.9300
C1—C2	1.498 (4)	C24—H24	0.9300
C4—C3	1.528 (4)	C22—H22	0.9300
C4—H4A	0.9700	C10—C15	1.383 (4)
C4—H4B	0.9700	C10—C11	1.413 (4)
C2—C3	1.529 (4)	C11—O1	1.280 (3)
C2—H2A	0.9700	C11—O1	1.280 (3)
C2—H2B	0.9700	C11—C12	1.504 (4)
C3—C8	1.524 (5)	C15—O2	1.304 (3)
C3—C7	1.527 (5)	C15—C14	1.490 (4)
C7—H7A	0.9600	C12—C13	1.524 (4)
C7—H7B	0.9600	C12—H12A	0.9700
C7—H7C	0.9600	C12—H12B	0.9700
C8—H8A	0.9600	C13—C16	1.514 (5)
C8—H8B	0.9600	C13—C14	1.523 (4)
C8—H8C	0.9600	C13—C17	1.536 (4)
C9—C18	1.520 (3)	C14—H14A	0.9700
C9—C10	1.522 (4)	C14—H14B	0.9700
C9—H9	0.9800	C16—H16A	0.9600
C20—C21	1.385 (4)	C16—H16B	0.9600
C20—C25	1.391 (4)	C16—H16C	0.9600
C20—C19	1.472 (4)	C17—H17A	0.9600
C18—C19	1.297 (4)	C17—H17B	0.9600
C18—H18	0.9300	C17—H17C	0.9600
C19—H19	0.9300	O3—H3	0.8200
C21—C22	1.381 (4)	O2—H2	0.8200
C5—C6—C1	117.4 (3)	C20—C21—H21	119.4
C5—C6—C9	120.6 (2)	C24—C25—C20	121.0 (3)
C1—C6—C9	122.0 (2)	C24—C25—H25	119.5
O3—C5—C6	123.2 (2)	C20—C25—H25	119.5
O3—C5—C4	113.6 (2)	C24—C23—C22	119.7 (3)
C6—C5—C4	123.2 (3)	C24—C23—H23	120.2
O4—C1—C6	122.0 (3)	C22—C23—H23	120.2
O4—C1—C2	116.4 (3)	C23—C24—C25	120.3 (3)
C6—C1—C2	121.6 (3)	C23—C24—H24	119.8
C5—C4—C3	114.5 (2)	C25—C24—H24	119.8
C5—C4—H4A	108.6	C23—C22—C21	120.0 (3)
C3—C4—H4A	108.6	C23—C22—H22	120.0
C5—C4—H4B	108.6	C21—C22—H22	120.0
C3—C4—H4B	108.6	C15—C10—C11	117.5 (3)
H4A—C4—H4B	107.6	C15—C10—C9	124.0 (2)
C1—C2—C3	114.7 (3)	C11—C10—C9	118.5 (2)
C1—C2—H2A	108.6	O1—C11—C10	122.4 (3)
C3—C2—H2A	108.6	O1—C11—C10	122.4 (3)
C1—C2—H2B	108.6	O1—C11—C12	116.5 (2)
C3—C2—H2B	108.6	O1—C11—C12	116.5 (2)
H2A—C2—H2B	107.6	C10—C11—C12	121.1 (3)
C8—C3—C7	109.4 (3)	O2—C15—C10	123.4 (3)
C8—C3—C4	109.6 (3)	O2—C15—C14	113.8 (3)
C7—C3—C4	110.1 (3)	C10—C15—C14	122.9 (3)
C8—C3—C2	110.1 (3)	C11—C12—C13	113.9 (2)
C7—C3—C2	110.4 (3)	C11—C12—H12A	108.8
C4—C3—C2	107.3 (3)	C13—C12—H12A	108.8
C3—C7—H7A	109.5	C11—C12—H12B	108.8
C3—C7—H7B	109.5	C13—C12—H12B	108.8
H7A—C7—H7B	109.5	H12A—C12—H12B	107.7
C3—C7—H7C	109.5	C16—C13—C14	111.0 (3)
H7A—C7—H7C	109.5	C16—C13—C12	109.8 (3)
H7B—C7—H7C	109.5	C14—C13—C12	106.9 (3)
C3—C8—H8A	109.5	C16—C13—C17	109.7 (3)
C3—C8—H8B	109.5	C14—C13—C17	109.4 (3)
H8A—C8—H8B	109.5	C12—C13—C17	110.0 (3)
C3—C8—H8C	109.5	C15—C14—C13	114.8 (3)
H8A—C8—H8C	109.5	C15—C14—H14A	108.6
H8B—C8—H8C	109.5	C13—C14—H14A	108.6
C6—C9—C18	113.8 (2)	C15—C14—H14B	108.6
C6—C9—C10	114.3 (2)	C13—C14—H14B	108.6
C18—C9—C10	113.0 (2)	H14A—C14—H14B	107.5
C6—C9—H9	104.8	C13—C16—H16A	109.5
C18—C9—H9	104.8	C13—C16—H16B	109.5
C10—C9—H9	104.8	H16A—C16—H16B	109.5
C21—C20—C25	117.8 (3)	C13—C16—H16C	109.5
C21—C20—C19	122.3 (3)	H16A—C16—H16C	109.5
C25—C20—C19	119.9 (3)	H16B—C16—H16C	109.5
C19—C18—C9	124.9 (3)	C13—C17—H17A	109.5
C19—C18—H18	117.6	C13—C17—H17B	109.5
C9—C18—H18	117.6	H17A—C17—H17B	109.5
C18—C19—C20	127.1 (3)	C13—C17—H17C	109.5
C18—C19—H19	116.4	H17A—C17—H17C	109.5
C20—C19—H19	116.4	H17B—C17—H17C	109.5
C22—C21—C20	121.1 (3)	C5—O3—H3	109.5
C22—C21—H21	119.4	C15—O2—H2	109.5
C1—C6—C5—O3	171.1 (3)	C19—C20—C25—C24	179.5 (3)
C9—C6—C5—O3	−6.2 (4)	C22—C23—C24—C25	0.3 (5)
C1—C6—C5—C4	−7.9 (4)	C20—C25—C24—C23	−0.7 (5)
C9—C6—C5—C4	174.8 (3)	C24—C23—C22—C21	0.4 (5)
C5—C6—C1—O4	−170.8 (3)	C20—C21—C22—C23	−0.6 (5)
C9—C6—C1—O4	6.5 (4)	C6—C9—C10—C15	87.1 (3)
C5—C6—C1—C2	7.5 (4)	C18—C9—C10—C15	−45.1 (4)
C9—C6—C1—C2	−175.2 (3)	C6—C9—C10—C11	−90.3 (3)
O3—C5—C4—C3	159.0 (3)	C18—C9—C10—C11	137.5 (2)
C6—C5—C4—C3	−21.9 (4)	C15—C10—C11—O1	−170.8 (3)
O4—C1—C2—C3	−159.0 (3)	C9—C10—C11—O1	6.7 (4)
C6—C1—C2—C3	22.6 (4)	C15—C10—C11—O1	−170.8 (3)
C5—C4—C3—C8	167.7 (3)	C9—C10—C11—O1	6.7 (4)
C5—C4—C3—C7	−72.0 (4)	C15—C10—C11—C12	7.2 (4)
C5—C4—C3—C2	48.1 (4)	C9—C10—C11—C12	−175.2 (2)
C1—C2—C3—C8	−167.7 (3)	C11—C10—C15—O2	168.1 (3)
C1—C2—C3—C7	71.4 (4)	C9—C10—C15—O2	−9.3 (4)
C1—C2—C3—C4	−48.5 (4)	C11—C10—C15—C14	−11.2 (4)
C5—C6—C9—C18	−135.7 (3)	C9—C10—C15—C14	171.5 (3)
C1—C6—C9—C18	47.1 (3)	O1—C11—C12—C13	−155.9 (3)
C5—C6—C9—C10	92.5 (3)	O1—C11—C12—C13	−155.9 (3)
C1—C6—C9—C10	−84.7 (3)	C10—C11—C12—C13	25.9 (4)
C6—C9—C18—C19	69.0 (4)	C11—C12—C13—C16	69.2 (4)
C10—C9—C18—C19	−158.5 (3)	C11—C12—C13—C14	−51.3 (4)
C9—C18—C19—C20	178.0 (3)	C11—C12—C13—C17	−170.0 (3)
C21—C20—C19—C18	18.1 (5)	O2—C15—C14—C13	162.1 (3)
C25—C20—C19—C18	−160.8 (3)	C10—C15—C14—C13	−18.5 (4)
C25—C20—C21—C22	0.1 (4)	C16—C13—C14—C15	−71.7 (4)
C19—C20—C21—C22	−178.9 (3)	C12—C13—C14—C15	48.0 (4)
C21—C20—C25—C24	0.5 (4)	C17—C13—C14—C15	167.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.82	1.82	2.610 (3)	163.
O3—H3···O1	0.82	1.85	2.640 (3)	160.
C19—H19···O4i	0.93	2.54	3.349 (3)	146.
C14—H14B···O1ii	0.97	2.59	3.439 (4)	146.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4	0.82	1.82	2.610 (3)	163
O3—H3⋯O1	0.82	1.85	2.640 (3)	160
C19—H19⋯O4i	0.93	2.54	3.349 (3)	146
C14—H14B⋯O1ii	0.97	2.59	3.439 (4)	146

Symmetry codes: (i) ; (ii) .