2,2′-[(1E)-3-Phenyl­prop-2-ene-1,1-di­yl]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one)

Zhu, Y.-L.; Xiao, G.-L.; Chen, Y.-F.; Chen, R.-T.; Zhou, Y.

doi:10.1107/S1600536811033745

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2398

doi:10.1107/S1600536811033745

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2,2′-[(1E)-3-Phenylprop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

Yu-Lin Zhu,^a ^* Guo-Lan Xiao,^a Yan-Fen Chen,^a Rui-Ting Chen ^a and Ying Zhou ^a

^aSchool of Chemistry and Environment, South China Normal University, Guangzhou 510006, People's Republic of China
^*Correspondence e-mail: yulinzhu2002@yahoo.com.cn

(Received 18 July 2011; accepted 18 August 2011; online 27 August 2011)

In the title molecule, C₂₅H₃₀O₄, the two cyclohexene rings adopt envelope conformations. The two hydroxy groups are involved in the formation of intramolecular O—H⋯O hydrogen bonds. In the crystal structure, weak intermolecular C—H⋯O hydrogen bonds link molecules 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_r = 394.49
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.071
wR(F²) = 0.154
S = 1.02
4149 reflections
269 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) x+1, y, z; (ii) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811033745/cv5137sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811033745/cv5137Isup3.cml

checkCIF report

Comment top

Tetraketones constitute an important class of organic compounds which can be used as dyes, fluorescent materials for visualization of biomolecules or in laser technologies due to their useful spectroscopic properties (Wang et al., 2006). The title compound is an aldol condensation/Michael addition compound which can be used as an intermediate during the synthesis of oxathene derivatives (Ali et al., 2011). When comes to the unactivated aldehydes such as cinnamaldehyde, the open chain structure can be obtained in a good yield (Ramachary & Mamillapalli, 2007; Rohr & Mahrwald, 2009). The reaction between cinnamaldehyde and 5,5-dimethyl-1,3-cyclohexanedione in the presence palladium(II) chloride proceeded to give the title compound (I) in isolated yield 82%.

In (I) (Fig. 1), the bond lengths and angles are normal and correspond to those observed in related structures (Bolte et al., 2001; Palakshi Reddy et al., 2010; Shi et al., 1998). Two six-membered cyclohexene rings adopt an envelope conformation. The phenyl ring C20–C25 is twisted at 18.1 (1)° from the C18═C19—C20 plane. The hydroxy groups and carbonyl O atoms face each other and form two intramolecular O—H···O hydrogen bonds (Table 1). There are weak intermolecular C19—H19···O4, C14—H14B···O1 and C9—H9···O2 interactions which link molecules into chains.

In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules related by translation along axis a into chains.

Related literature top

For the crystal structures of related compounds, 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 top

The title compound has been synthesized following the known procedures (Ramachary & Mamillapalli, 2007; Rohr & Mahrwald, 2009). A mixture of cinnamaldehyde (0.66 g, 5 mmol), 5,5-dimethyl-1,3-cyclohexanedione (1.40 g, 10 mmol), and palladium (II) chloride (0.0010 g) was refluxed in acetonitrile (10 ml) at 353 K for 6 h (Fig. 2). After being cooled to room temperature, the reaction mixture was poured into water. The white precipitate was filtered off with a silica pad, washed twice with water, and the filtrate was then dried under vacuum to yield the product in yield of 82%. Single crystals of the title compound were obtained by slow evaporation from ethanol at room temperature to yield colourless, block-shaped crystals.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Palladium(II) chloride catalyzed synthesis of the title compound.

2,2'-[(1E)-3-Phenylprop-2-ene-1,1-diyl]bis(3-hydroxy-5,5- dimethylcyclohex-2-en-1-one) top

Crystal data top

C₂₅H₃₀O₄	Z = 2
M_r = 394.49	F(000) = 424
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.019P)² + 1.9414P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4149 reflections	Δρ_max = 0.29 e Å⁻³
269 parameters	Δρ_min = −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)

Crystal data top

C₂₅H₃₀O₄	γ = 76.927 (3)°
M_r = 394.49	V = 1096.9 (5) Å³
Triclinic, P1	Z = 2
a = 5.9465 (15) Å	Mo Kα radiation
b = 11.214 (3) Å	µ = 0.08 mm⁻¹
c = 17.170 (4) Å	T = 293 K
α = 82.804 (3)°	0.30 × 0.28 × 0.20 mm
β = 81.062 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	4149 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	3560 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.984	R_int = 0.020
11804 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.02	Δρ_max = 0.29 e Å⁻³
4149 reflections	Δρ_min = −0.20 e Å⁻³
269 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y, z; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₅H₃₀O₄
M_r	394.49
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.9465 (15), 11.214 (3), 17.170 (4)
α, β, γ (°)	82.804 (3), 81.062 (3), 76.927 (3)
V (Å³)	1096.9 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.28 × 0.20

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.977, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	11804, 4149, 3560
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.154, 1.02
No. of reflections	4149
No. of parameters	269
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.20

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4	0.82	1.82	2.610 (3)	162.7
O3—H3···O1	0.82	1.85	2.640 (3)	160.1
C19—H19···O4ⁱ	0.93	2.54	3.349 (3)	146.3
C14—H14B···O1ⁱⁱ	0.97	2.59	3.439 (4)	146.0

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Acknowledgements

The authors thank South China Normal University for financial support (grant No. SCNU G21096).

References

Ali, J., Majid, M. H. & Fatemeh, F. B. (2011). E-J. Chem. 8, 910–916. Google Scholar
Bolte, M., Degen, A. & Rühl, S. (2001). Acta Cryst. C57, 446–451. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Palakshi Reddy, B., Vijayakumar, V., Sarveswari, S., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2806–o2807. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ramachary, D. B. & Mamillapalli, K. (2007). J. Org. Chem. 72, 5056–5068. CrossRef CAS Google Scholar
Rohr, K. & Mahrwald, R. (2009). Bioorg. Med. Chem. Lett. 19, 3949–3951. CrossRef CAS Google Scholar
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Volume 67| Part 9| September 2011| Page o2398

doi:10.1107/S1600536811033745

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,2′-[(1E)-3-Phenyl­prop-2-ene-1,1-di­yl]bis­­(3-hy­dr­oxy-5,5-di­methyl­cyclo­hex-2-en-1-one)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,2′-[(1E)-3-Phenylprop-2-ene-1,1-diyl]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)