2,2′-[(4-Eth­oxy­phen­yl)methyl­ene]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one)

Sureshbabu, N.; Sughanya, V.

doi:10.1107/S1600536812033934

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2638

doi:10.1107/S1600536812033934

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2,2′-[(4-Ethoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)

N. Sureshbabu ^a and V. Sughanya ^a ^*

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India
^*Correspondence e-mail: saisukanyashri@gmail.com

(Received 24 July 2012; accepted 29 July 2012; online 4 August 2012)

In the title compound, C₂₅H₃₂O₅, the two cyclohexenone rings have envelope conformations with the C atom bearing two methyl groups as the flap atom in each ring. Relatively strong intramolecular O—H⋯O hydrogen bonds are observed.

Related literature

For the synthesis of bisdimedones, see: Vang & Stankevich (1960 ); Hilderbrand & Weissleder (2007 ). For their pharmaceutical properties, see: Lambert et al. (1997 ); Poupelin et al. (1978 ); Hideo (1981 ); Selvanayagam et al. (1996 ); Jonathan et al. (1988 ). For the crystal structures of related xanthene derivatives, see: Odabaşoğlu et al. (2008 ); Mehdi et al. (2011 ); Ravikumar et al. (2012 ). For the assignment of ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₅H₃₂O₅
M_r = 412.51
Monoclinic, P 2₁ /n
a = 9.774 (5) Å
b = 10.698 (5) Å
c = 21.578 (5) Å
β = 93.735 (5)°
V = 2251.5 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.961, T_max = 0.989
17055 measured reflections
3962 independent reflections
3065 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.122
S = 1.03
3962 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O5	0.82	1.83	2.631 (2)	164
O4—H4A⋯O2	0.82	1.78	2.5864 (19)	167

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812033934/wn2485sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812033934/wn2485Isup2.hkl

checkCIF report

Comment top

Several methods have been reported in the literature (Vang & Stankevich, 1960; Hilderbrand & Weissleder, 2007) for the synthesis of the title compound. Xanthene derivatives possess biological properties such as antibacterial, antiviral and anti-inflammatory activities (Jonathan et al., 1988) and are therefore used in medicine.

In the title compound, the cyclohexenone rings C10–C15 and C18–C23 both adopt envelope conformations, with flap atoms C13 and C21, respectively.The dihedral angle between the two cyclohexenone planes Q(C10/C11/C12/C14/C15) and R(C18/C19/C20/C22/C23) is 58.42 (3)°. The dihedral angle between the benzene ring P(C3–C8) and cyclohexenone planes Q and R are 66.37 (3)° and 61.41 (4)°, respectively.. The hydroxy and carbonyl oxygen atoms face each other and are oriented to allow for the formation of two intramolecular O—H···O hydrogen bonds (Table 1, Fig. 2), typical for xanthene derivatives.

Related literature top

For the synthesis of bisdimedones, see: Vang & Stankevich (1960); Hilderbrand & Weissleder (2007). For their pharmaceutical properties, see: Lambert et al. (1997); Poupelin et al. (1978); Hideo (1981); Selvanayagam et al. (1996); Jonathan et al. (1988). For the crystal structures of related xanthene derivatives, see: Odabaşoğlu et al. (2008); Mehdi et al. (2011); Ravikumar et al. (2012). For the assignment of ring conformations, see: Cremer & Pople (1975).

Experimental top

The title compound was prepared in a single stage. A mixture of 4-Ethoxybenzaldehyde (1.2g, 8 mmol), 5,5-dimethylcyclohexane-1,3-dione (2.24g, 16 mmol) and 20ml of ethanol was heated to 70 °C for about 10 minutes. The reaction mixture was allowed to cool to room temperature and the resulting title compound, 2,2'-((4-ethoxyphenyl)methylene) bis(3-hydroxy-5,5-dimethylcyclohex-2-enone) was filtered and dried (M.p. 411 K; Yield 78% ).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
	Fig. 2. A view of the packing in the crystal structure, showing intramolecular O—H···O hydrogen bonds as dotted lines.

2,2'-[(4-Ethoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one) top

Crystal data top

C₂₅H₃₂O₅	F(000) = 888
M_r = 412.51	D_x = 1.217 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.774 (5) Å	Cell parameters from 6149 reflections
b = 10.698 (5) Å	θ = 2.1–27.1°
c = 21.578 (5) Å	µ = 0.08 mm⁻¹
β = 93.735 (5)°	T = 293 K
V = 2251.5 (16) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3962 independent reflections
Radiation source: fine-focus sealed tube	3065 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scan	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→7
T_min = 0.961, T_max = 0.989	k = −12→12
17055 measured reflections	l = −24→25

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0573P)² + 0.7618P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3962 reflections	Δρ_max = 0.24 e Å⁻³
272 parameters	Δρ_min = −0.23 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: 0.0143 (14)

Crystal data top

C₂₅H₃₂O₅	V = 2251.5 (16) Å³
M_r = 412.51	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.774 (5) Å	µ = 0.08 mm⁻¹
b = 10.698 (5) Å	T = 293 K
c = 21.578 (5) Å	0.30 × 0.20 × 0.20 mm
β = 93.735 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3962 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3065 reflections with I > 2σ(I)
T_min = 0.961, T_max = 0.989	R_int = 0.028
17055 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
3962 reflections	Δρ_min = −0.23 e Å⁻³
272 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.1136 (3)	0.5154 (3)	0.33826 (11)	0.0776 (7)
H1A	0.1550	0.5226	0.2993	0.116*
H1B	0.0836	0.5964	0.3510	0.116*
H1C	0.0363	0.4600	0.3337	0.116*
C2	0.2151 (2)	0.4651 (3)	0.38572 (10)	0.0707 (7)
H2A	0.2457	0.3831	0.3732	0.085*
H2B	0.2943	0.5198	0.3900	0.085*
C3	0.22806 (19)	0.40529 (19)	0.49280 (8)	0.0495 (5)
C4	0.3642 (2)	0.3757 (2)	0.49343 (9)	0.0567 (6)
H4	0.4129	0.3911	0.4586	0.068*
C5	0.42951 (19)	0.32300 (19)	0.54571 (9)	0.0518 (5)
H5	0.5221	0.3032	0.5452	0.062*
C6	0.36275 (17)	0.29861 (16)	0.59866 (7)	0.0368 (4)
C7	0.22621 (18)	0.33226 (18)	0.59738 (8)	0.0474 (5)
H7	0.1781	0.3191	0.6326	0.057*
C8	0.15904 (19)	0.3846 (2)	0.54565 (9)	0.0547 (5)
H8	0.0669	0.4061	0.5463	0.066*
C9	0.44542 (16)	0.24953 (15)	0.65658 (7)	0.0350 (4)
H9	0.4980	0.3224	0.6720	0.042*
C10	0.55496 (16)	0.15470 (16)	0.64172 (7)	0.0359 (4)
C11	0.52716 (17)	0.05495 (16)	0.60035 (7)	0.0373 (4)
C12	0.63981 (18)	−0.02547 (18)	0.57850 (8)	0.0474 (5)
H12A	0.6192	−0.0451	0.5350	0.057*
H12B	0.6408	−0.1035	0.6014	0.057*
C13	0.78274 (18)	0.0323 (2)	0.58573 (8)	0.0497 (5)
C14	0.80122 (19)	0.0814 (2)	0.65212 (9)	0.0564 (5)
H14A	0.8101	0.0108	0.6803	0.068*
H14B	0.8858	0.1288	0.6566	0.068*
C15	0.68583 (18)	0.16245 (18)	0.67054 (8)	0.0433 (4)
C16	0.7976 (2)	0.1388 (2)	0.53921 (10)	0.0651 (6)
H16A	0.8883	0.1733	0.5446	0.098*
H16B	0.7314	0.2027	0.5462	0.098*
H16C	0.7825	0.1071	0.4977	0.098*
C17	0.8898 (2)	−0.0678 (2)	0.57416 (11)	0.0714 (7)
H17A	0.8820	−0.1349	0.6033	0.107*
H17B	0.9798	−0.0319	0.5793	0.107*
H17C	0.8746	−0.0994	0.5326	0.107*
C18	0.36132 (16)	0.21294 (15)	0.71075 (7)	0.0341 (4)
C19	0.25324 (17)	0.12859 (16)	0.70621 (8)	0.0373 (4)
C20	0.1721 (2)	0.09839 (17)	0.76079 (9)	0.0472 (5)
H20A	0.2115	0.0251	0.7815	0.057*
H20B	0.0790	0.0777	0.7459	0.057*
C21	0.16771 (18)	0.20449 (17)	0.80774 (8)	0.0434 (4)
C22	0.31497 (19)	0.24452 (19)	0.82458 (8)	0.0457 (5)
H22A	0.3135	0.3233	0.8468	0.055*
H22B	0.3576	0.1829	0.8526	0.055*
C23	0.40218 (18)	0.25987 (16)	0.77023 (8)	0.0394 (4)
C24	0.08261 (19)	0.31254 (19)	0.78021 (9)	0.0516 (5)
H24A	0.0811	0.3791	0.8100	0.077*
H24B	−0.0093	0.2845	0.7698	0.077*
H24C	0.1224	0.3422	0.7434	0.077*
C25	0.1019 (2)	0.1593 (2)	0.86609 (10)	0.0667 (6)
H25A	0.1000	0.2266	0.8954	0.100*
H25B	0.1543	0.0912	0.8842	0.100*
H25C	0.0099	0.1318	0.8552	0.100*
O1	0.15317 (15)	0.45642 (16)	0.44304 (6)	0.0703 (5)
O2	0.40539 (12)	0.02575 (12)	0.58061 (5)	0.0467 (3)
O3	0.71819 (13)	0.23817 (14)	0.71624 (6)	0.0597 (4)
H3A	0.6481	0.2663	0.7299	0.072*
O4	0.21555 (12)	0.06855 (12)	0.65595 (6)	0.0477 (3)
H4A	0.2793	0.0663	0.6331	0.057*
O5	0.51622 (13)	0.31629 (13)	0.78119 (6)	0.0527 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0780 (16)	0.0951 (18)	0.0589 (14)	−0.0061 (14)	−0.0029 (12)	0.0242 (13)
C2	0.0646 (14)	0.0954 (18)	0.0529 (13)	0.0138 (12)	0.0107 (11)	0.0272 (13)
C3	0.0478 (11)	0.0603 (12)	0.0411 (10)	0.0145 (9)	0.0076 (8)	0.0138 (9)
C4	0.0508 (12)	0.0773 (14)	0.0440 (11)	0.0176 (10)	0.0187 (9)	0.0229 (10)
C5	0.0379 (10)	0.0693 (13)	0.0497 (11)	0.0141 (9)	0.0138 (8)	0.0178 (10)
C6	0.0370 (9)	0.0376 (9)	0.0365 (9)	0.0018 (7)	0.0066 (7)	0.0024 (7)
C7	0.0406 (10)	0.0626 (12)	0.0405 (10)	0.0109 (9)	0.0132 (8)	0.0102 (9)
C8	0.0390 (10)	0.0751 (14)	0.0510 (11)	0.0181 (9)	0.0117 (8)	0.0158 (10)
C9	0.0330 (8)	0.0373 (9)	0.0349 (9)	−0.0032 (7)	0.0035 (7)	−0.0011 (7)
C10	0.0345 (9)	0.0440 (10)	0.0294 (8)	0.0006 (7)	0.0034 (7)	0.0028 (7)
C11	0.0385 (9)	0.0458 (10)	0.0278 (8)	0.0013 (7)	0.0036 (7)	0.0048 (7)
C12	0.0498 (11)	0.0536 (11)	0.0393 (10)	0.0099 (9)	0.0070 (8)	−0.0028 (9)
C13	0.0400 (10)	0.0690 (13)	0.0404 (10)	0.0151 (9)	0.0056 (8)	0.0012 (9)
C14	0.0379 (10)	0.0842 (15)	0.0464 (11)	0.0132 (10)	−0.0034 (8)	−0.0067 (11)
C15	0.0369 (9)	0.0597 (11)	0.0334 (9)	−0.0015 (8)	0.0019 (7)	−0.0024 (9)
C16	0.0528 (13)	0.0821 (16)	0.0623 (13)	0.0027 (11)	0.0171 (10)	0.0066 (12)
C17	0.0564 (13)	0.0975 (18)	0.0607 (13)	0.0304 (12)	0.0077 (10)	−0.0055 (13)
C18	0.0346 (9)	0.0354 (9)	0.0325 (9)	0.0014 (7)	0.0043 (7)	−0.0005 (7)
C19	0.0379 (9)	0.0359 (9)	0.0384 (9)	0.0019 (7)	0.0056 (7)	−0.0020 (8)
C20	0.0492 (11)	0.0432 (10)	0.0509 (11)	−0.0054 (8)	0.0168 (8)	0.0013 (9)
C21	0.0460 (10)	0.0459 (10)	0.0397 (10)	0.0004 (8)	0.0142 (8)	0.0002 (8)
C22	0.0494 (11)	0.0536 (11)	0.0347 (10)	0.0085 (9)	0.0067 (8)	−0.0011 (8)
C23	0.0386 (9)	0.0394 (9)	0.0405 (10)	0.0030 (8)	0.0048 (7)	−0.0019 (8)
C24	0.0437 (11)	0.0551 (12)	0.0569 (12)	0.0061 (9)	0.0096 (9)	−0.0031 (10)
C25	0.0746 (15)	0.0732 (15)	0.0559 (13)	−0.0010 (12)	0.0305 (11)	0.0050 (11)
O1	0.0564 (9)	0.1055 (13)	0.0500 (8)	0.0307 (8)	0.0115 (7)	0.0312 (8)
O2	0.0411 (7)	0.0590 (8)	0.0398 (7)	−0.0045 (6)	0.0008 (5)	−0.0075 (6)
O3	0.0373 (7)	0.0860 (10)	0.0556 (8)	−0.0051 (7)	0.0016 (6)	−0.0234 (8)
O4	0.0441 (7)	0.0527 (8)	0.0472 (7)	−0.0104 (6)	0.0099 (6)	−0.0117 (6)
O5	0.0459 (8)	0.0660 (9)	0.0460 (7)	−0.0096 (6)	0.0029 (6)	−0.0164 (7)

Geometric parameters (Å, º) top

C1—C2	1.481 (3)	C14—C15	1.497 (3)
C1—H1A	0.9600	C14—H14A	0.9700
C1—H1B	0.9600	C14—H14B	0.9700
C1—H1C	0.9600	C15—O3	1.299 (2)
C2—O1	1.415 (2)	C16—H16A	0.9600
C2—H2A	0.9700	C16—H16B	0.9600
C2—H2B	0.9700	C16—H16C	0.9600
C3—C4	1.367 (3)	C17—H17A	0.9600
C3—O1	1.373 (2)	C17—H17B	0.9600
C3—C8	1.380 (3)	C17—H17C	0.9600
C4—C5	1.380 (3)	C18—C19	1.388 (2)
C4—H4	0.9300	C18—C23	1.411 (2)
C5—C6	1.377 (2)	C19—O4	1.293 (2)
C5—H5	0.9300	C19—C20	1.497 (2)
C6—C7	1.381 (2)	C20—C21	1.524 (3)
C6—C9	1.536 (2)	C20—H20A	0.9700
C7—C8	1.377 (3)	C20—H20B	0.9700
C7—H7	0.9300	C21—C24	1.522 (3)
C8—H8	0.9300	C21—C22	1.523 (3)
C9—C18	1.523 (2)	C21—C25	1.529 (3)
C9—C10	1.524 (2)	C22—C23	1.503 (2)
C9—H9	0.9800	C22—H22A	0.9700
C10—C15	1.388 (2)	C22—H22B	0.9700
C10—C11	1.406 (2)	C23—O5	1.276 (2)
C11—O2	1.276 (2)	C24—H24A	0.9600
C11—C12	1.497 (2)	C24—H24B	0.9600
C12—C13	1.526 (3)	C24—H24C	0.9600
C12—H12A	0.9700	C25—H25A	0.9600
C12—H12B	0.9700	C25—H25B	0.9600
C13—C14	1.525 (3)	C25—H25C	0.9600
C13—C17	1.529 (3)	O3—H3A	0.8200
C13—C16	1.531 (3)	O4—H4A	0.8200

C2—C1—H1A	109.5	H14A—C14—H14B	107.7
C2—C1—H1B	109.5	O3—C15—C10	123.30 (17)
H1A—C1—H1B	109.5	O3—C15—C14	114.36 (15)
C2—C1—H1C	109.5	C10—C15—C14	122.33 (16)
H1A—C1—H1C	109.5	C13—C16—H16A	109.5
H1B—C1—H1C	109.5	C13—C16—H16B	109.5
O1—C2—C1	108.82 (19)	H16A—C16—H16B	109.5
O1—C2—H2A	109.9	C13—C16—H16C	109.5
C1—C2—H2A	109.9	H16A—C16—H16C	109.5
O1—C2—H2B	109.9	H16B—C16—H16C	109.5
C1—C2—H2B	109.9	C13—C17—H17A	109.5
H2A—C2—H2B	108.3	C13—C17—H17B	109.5
C4—C3—O1	124.68 (16)	H17A—C17—H17B	109.5
C4—C3—C8	118.85 (17)	C13—C17—H17C	109.5
O1—C3—C8	116.46 (16)	H17A—C17—H17C	109.5
C3—C4—C5	120.04 (17)	H17B—C17—H17C	109.5
C3—C4—H4	120.0	C19—C18—C23	117.68 (15)
C5—C4—H4	120.0	C19—C18—C9	124.00 (15)
C6—C5—C4	122.47 (17)	C23—C18—C9	118.13 (14)
C6—C5—H5	118.8	O4—C19—C18	123.79 (15)
C4—C5—H5	118.8	O4—C19—C20	114.57 (15)
C5—C6—C7	116.33 (16)	C18—C19—C20	121.63 (15)
C5—C6—C9	119.16 (15)	C19—C20—C21	113.67 (15)
C7—C6—C9	124.19 (15)	C19—C20—H20A	108.8
C8—C7—C6	122.12 (16)	C21—C20—H20A	108.8
C8—C7—H7	118.9	C19—C20—H20B	108.8
C6—C7—H7	118.9	C21—C20—H20B	108.8
C7—C8—C3	120.15 (17)	H20A—C20—H20B	107.7
C7—C8—H8	119.9	C24—C21—C22	111.33 (16)
C3—C8—H8	119.9	C24—C21—C20	110.15 (16)
C18—C9—C10	114.33 (14)	C22—C21—C20	107.52 (15)
C18—C9—C6	115.51 (13)	C24—C21—C25	108.22 (16)
C10—C9—C6	113.32 (13)	C22—C21—C25	109.52 (16)
C18—C9—H9	103.9	C20—C21—C25	110.09 (16)
C10—C9—H9	103.9	C23—C22—C21	114.81 (14)
C6—C9—H9	103.9	C23—C22—H22A	108.6
C15—C10—C11	117.65 (16)	C21—C22—H22A	108.6
C15—C10—C9	120.37 (15)	C23—C22—H22B	108.6
C11—C10—C9	121.95 (14)	C21—C22—H22B	108.6
O2—C11—C10	122.34 (15)	H22A—C22—H22B	107.5
O2—C11—C12	116.30 (16)	O5—C23—C18	121.93 (16)
C10—C11—C12	121.34 (15)	O5—C23—C22	116.10 (15)
C11—C12—C13	114.95 (16)	C18—C23—C22	121.96 (16)
C11—C12—H12A	108.5	C21—C24—H24A	109.5
C13—C12—H12A	108.5	C21—C24—H24B	109.5
C11—C12—H12B	108.5	H24A—C24—H24B	109.5
C13—C12—H12B	108.5	C21—C24—H24C	109.5
H12A—C12—H12B	107.5	H24A—C24—H24C	109.5
C14—C13—C12	106.67 (15)	H24B—C24—H24C	109.5
C14—C13—C17	110.72 (16)	C21—C25—H25A	109.5
C12—C13—C17	109.32 (18)	C21—C25—H25B	109.5
C14—C13—C16	110.46 (19)	H25A—C25—H25B	109.5
C12—C13—C16	111.08 (16)	C21—C25—H25C	109.5
C17—C13—C16	108.59 (17)	H25A—C25—H25C	109.5
C15—C14—C13	113.79 (15)	H25B—C25—H25C	109.5
C15—C14—H14A	108.8	C3—O1—C2	118.21 (15)
C13—C14—H14A	108.8	C15—O3—H3A	109.5
C15—C14—H14B	108.8	C19—O4—H4A	109.5
C13—C14—H14B	108.8

O1—C3—C4—C5	−179.1 (2)	C9—C10—C15—O3	8.8 (3)
C8—C3—C4—C5	1.7 (3)	C11—C10—C15—C14	9.3 (3)
C3—C4—C5—C6	−0.3 (3)	C9—C10—C15—C14	−172.57 (17)
C4—C5—C6—C7	−1.3 (3)	C13—C14—C15—O3	−157.30 (18)
C4—C5—C6—C9	−175.17 (19)	C13—C14—C15—C10	24.0 (3)
C5—C6—C7—C8	1.5 (3)	C10—C9—C18—C19	−79.6 (2)
C9—C6—C7—C8	175.01 (18)	C6—C9—C18—C19	54.6 (2)
C6—C7—C8—C3	−0.1 (3)	C10—C9—C18—C23	95.19 (18)
C4—C3—C8—C7	−1.6 (3)	C6—C9—C18—C23	−130.60 (16)
O1—C3—C8—C7	179.2 (2)	C23—C18—C19—O4	−172.22 (15)
C5—C6—C9—C18	−174.17 (16)	C9—C18—C19—O4	2.6 (3)
C7—C6—C9—C18	12.5 (2)	C23—C18—C19—C20	6.6 (2)
C5—C6—C9—C10	−39.5 (2)	C9—C18—C19—C20	−178.58 (15)
C7—C6—C9—C10	147.15 (18)	O4—C19—C20—C21	−152.94 (16)
C18—C9—C10—C15	−89.34 (19)	C18—C19—C20—C21	28.2 (2)
C6—C9—C10—C15	135.45 (16)	C19—C20—C21—C24	69.2 (2)
C18—C9—C10—C11	88.71 (18)	C19—C20—C21—C22	−52.3 (2)
C6—C9—C10—C11	−46.5 (2)	C19—C20—C21—C25	−171.51 (17)
C15—C10—C11—O2	166.58 (16)	C24—C21—C22—C23	−75.1 (2)
C9—C10—C11—O2	−11.5 (2)	C20—C21—C22—C23	45.6 (2)
C15—C10—C11—C12	−11.6 (2)	C25—C21—C22—C23	165.22 (16)
C9—C10—C11—C12	170.32 (15)	C19—C18—C23—O5	165.19 (16)
O2—C11—C12—C13	162.12 (15)	C9—C18—C23—O5	−10.0 (2)
C10—C11—C12—C13	−19.6 (2)	C19—C18—C23—C22	−13.8 (2)
C11—C12—C13—C14	49.0 (2)	C9—C18—C23—C22	171.03 (15)
C11—C12—C13—C17	168.76 (16)	C21—C22—C23—O5	166.69 (16)
C11—C12—C13—C16	−71.4 (2)	C21—C22—C23—C18	−14.3 (2)
C12—C13—C14—C15	−50.8 (2)	C4—C3—O1—C2	8.4 (3)
C17—C13—C14—C15	−169.63 (19)	C8—C3—O1—C2	−172.5 (2)
C16—C13—C14—C15	70.0 (2)	C1—C2—O1—C3	176.6 (2)
C11—C10—C15—O3	−169.30 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5	0.82	1.83	2.631 (2)	164
O4—H4A···O2	0.82	1.78	2.5864 (19)	167

Experimental details

Crystal data
Chemical formula	C₂₅H₃₂O₅
M_r	412.51
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.774 (5), 10.698 (5), 21.578 (5)
β (°)	93.735 (5)
V (Å³)	2251.5 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.961, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	17055, 3962, 3065
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.122, 1.03
No. of reflections	3962
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O5	0.82	1.83	2.631 (2)	163.8
O4—H4A···O2	0.82	1.78	2.5864 (19)	167.0

Acknowledgements

The authors thank Dr Babu Varghese and the SAIF, IIT Madras, for the data collection.

References

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Volume 68| Part 9| September 2012| Page o2638

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

2,2′-[(4-Eth­­oxy­phen­yl)methyl­ene]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′-[(4-Ethoxyphenyl)methylene]bis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-one)