2,2'-[(4-Eth-oxy-phen-yl)methyl-ene]bis-(3-hy-droxy-5,5-dimethyl-cyclo-hex-2-en-1-one).

In the title compound, C(25)H(32)O(5), the two cyclo-hexenone rings have envelope conformations with the C atom bearing two methyl groups as the flap atom in each ring. Relatively strong intra-molecular 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 = 412.51

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.03

3962 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.23 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812033934/wn2485sup1.cif

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

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

C25H32O5	F(000) = 888
Mr = 412.51	Dx = 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

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

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(Fo2) + (0.0573P)2 + 0.7618P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3962 reflections	Δρmax = 0.24 e Å−3
272 parameters	Δρmin = −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)

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	0.1136 (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)

	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)

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)

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

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