9-(2,3-Dichloro-phen-yl)-4a-hydr-oxy-3,3,6,6-tetra-methyl-4,4a,5,6,9,9a-hexa-hydro-3H-xanthene-1,8(2H,7H)-dione.

Mol-ecules of the title compound, C(23)H(26)Cl(2)O(4), are linked by hydrogen bonds between the hydroxyl O atom and the carbonyl O atom of a neighboring mol-ecule. The central hydropyran and fused cyclohexanone rings adopt half-chair conformations, while the fused hydroxycyclohexanone ring adopts a chair conformation.

Related literature

For the synthesis of xanthenes, see: Kantevari et al. (2006 ▶); Lin et al. (2007 ▶). For therapeutic effects, see: Sirkecioglu et al. (1995 ▶).

Experimental

Crystal data

C23H26Cl2O4

M = 437.34

Monoclinic,

a = 11.9581 (17) Å

b = 15.165 (2) Å

c = 12.3953 (18) Å

β = 105.357 (13)°

V = 2167.5 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 290 (2) K

0.22 × 0.10 × 0.09 mm

Data collection

Stoe IPDS diffractometer

Absorption correction: numerical (X-RED; Stoe & Cie, 1997 ▶) T min = 0.930, T max = 0.969

13922 measured reflections

4012 independent reflections

1511 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.162

S = 0.85

4012 reflections

246 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.83 e Å−3

Data collection: IPDS Software (Stoe & Cie, 1997 ▶); cell refinement: IPDS Software; data reduction: IPDS Software; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2001 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808002183/ng2413sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002183/ng2413Isup2.hkl

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

C23H26Cl2O4	F000 = 920
Mr = 437.34	Dx = 1.340 Mg m−3
Monoclinic, P21/a	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 13922 reflections
a = 11.9581 (17) Å	θ = 3.3–25.5º
b = 15.165 (2) Å	µ = 0.33 mm−1
c = 12.3953 (18) Å	T = 290 (2) K
β = 105.357 (13)º	Block shape, colorless
V = 2167.5 (5) Å3	0.22 × 0.10 × 0.09 mm
Z = 4

Stoe IPDS diffractometer	4012 independent reflections
Radiation source: fine-focus sealed tube	1511 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.070
T = 290(2) K	θmax = 25.5º
φ oscillation scans	θmin = 3.7º
Absorption correction: numerical(X-RED; Stoe & Cie, 1997)	h = −14→12
Tmin = 0.930, Tmax = 0.969	k = −17→18
13922 measured reflections	l = −15→15

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.060	w = 1/[σ2(Fo2) + (0.08P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.162	(Δ/σ)max < 0.001
S = 0.85	Δρmax = 0.73 e Å−3
4012 reflections	Δρmin = −0.83 e Å−3
246 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0056 (13)
Secondary atom site location: difference Fourier map

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
Cl1	0.74989 (9)	0.77065 (8)	−0.11681 (10)	0.0535 (4)
Cl2	0.80090 (12)	0.65780 (9)	−0.30989 (10)	0.0694 (5)
O1	1.1085 (2)	0.84256 (18)	0.2731 (2)	0.0445 (8)
O2	1.1313 (2)	0.8477 (2)	0.0944 (3)	0.0469 (9)
H22	1.197 (4)	0.851 (3)	0.130 (4)	0.056*
O3	0.8621 (3)	0.59442 (19)	0.2062 (3)	0.0532 (9)
O4	0.7952 (3)	0.8634 (2)	0.2112 (3)	0.0571 (9)
C1	0.9390 (3)	0.8517 (3)	0.1106 (3)	0.0315 (10)
H1	0.9188	0.8699	0.0319	0.038*
C2	0.9459 (3)	0.7008 (3)	0.0160 (4)	0.0337 (11)
C3	0.9198 (3)	0.7533 (3)	0.1118 (3)	0.0365 (11)
H3	0.8371	0.7449	0.1056	0.044*
C4	0.8591 (4)	0.9029 (3)	0.1672 (4)	0.0398 (11)
C5	1.0648 (3)	0.8800 (3)	0.1620 (4)	0.0347 (11)
C6	1.0712 (4)	0.7622 (3)	0.2944 (4)	0.0415 (11)
C7	1.0802 (3)	0.9788 (3)	0.1793 (3)	0.0367 (11)
H7A	1.0751	1.0057	0.1071	0.044*
H7B	1.1580	0.9894	0.2259	0.044*
C8	0.8930 (4)	0.6534 (3)	−0.1764 (4)	0.0487 (13)
C9	0.8717 (4)	0.7044 (3)	−0.0908 (4)	0.0370 (11)
C10	0.8714 (4)	0.9994 (3)	0.1684 (4)	0.0447 (12)
H10A	0.8157	1.0256	0.2034	0.054*
H10B	0.8549	1.0211	0.0922	0.054*
C11	1.0414 (4)	0.6451 (3)	0.0339 (4)	0.0473 (12)
H11	1.0932	0.6423	0.1045	0.057*
C12	0.9942 (4)	1.0271 (3)	0.2326 (4)	0.0397 (11)
C13	0.9474 (4)	0.6348 (3)	0.2614 (4)	0.0507 (13)
C14	0.9840 (4)	0.7182 (3)	0.2255 (4)	0.0408 (11)
C15	1.0604 (4)	0.5943 (3)	−0.0507 (5)	0.0589 (14)
H15	1.1234	0.5560	−0.0362	0.071*
C16	1.1378 (5)	0.7305 (4)	0.4066 (5)	0.0905 (10)
H16A	1.2129	0.7097	0.4012	0.109*
H16B	1.1513	0.7801	0.4578	0.109*
C17	1.0136 (4)	1.0051 (3)	0.3568 (4)	0.0621 (15)
H17A	0.9625	1.0401	0.3874	0.093*
H17B	1.0926	1.0176	0.3961	0.093*
H17C	0.9978	0.9437	0.3648	0.093*
C18	0.9873 (5)	0.5992 (3)	−0.1572 (5)	0.0559 (14)
H18	1.0021	0.5661	−0.2151	0.067*
C19	1.0103 (4)	1.1263 (3)	0.2207 (4)	0.0597 (14)
H19A	0.9918	1.1416	0.1428	0.090*
H19B	1.0893	1.1419	0.2559	0.090*
H19C	0.9598	1.1576	0.2559	0.090*
C20	1.0817 (5)	0.6589 (4)	0.4551 (5)	0.0905 (10)
C21	1.0208 (5)	0.5970 (4)	0.3675 (4)	0.0905 (10)
H21A	0.9719	0.5596	0.3993	0.109*
H21B	1.0785	0.5593	0.3489	0.109*
C22	1.1532 (5)	0.6224 (4)	0.5598 (5)	0.0905 (10)
H22A	1.2121	0.5851	0.5443	0.136*
H22B	1.1055	0.5884	0.5955	0.136*
H22C	1.1891	0.6696	0.6083	0.136*
C23	0.9799 (5)	0.7069 (4)	0.4916 (5)	0.0905 (10)
H23A	0.9306	0.6636	0.5120	0.136*
H23B	0.9354	0.7416	0.4303	0.136*
H23C	1.0119	0.7446	0.5544	0.136*

	U11	U22	U33	U12	U13	U23
Cl1	0.0437 (7)	0.0653 (9)	0.0458 (8)	0.0066 (6)	0.0019 (6)	−0.0049 (6)
Cl2	0.0873 (10)	0.0793 (10)	0.0415 (8)	−0.0153 (8)	0.0171 (7)	−0.0107 (7)
O1	0.0449 (18)	0.0365 (19)	0.045 (2)	−0.0107 (15)	−0.0013 (15)	0.0099 (15)
O2	0.0329 (18)	0.050 (2)	0.058 (2)	0.0001 (17)	0.0121 (16)	−0.0025 (17)
O3	0.049 (2)	0.0415 (19)	0.063 (2)	−0.0143 (16)	0.0030 (17)	0.0017 (16)
O4	0.044 (2)	0.063 (2)	0.070 (2)	−0.0123 (17)	0.0261 (18)	−0.0110 (18)
C1	0.030 (2)	0.030 (3)	0.031 (2)	−0.002 (2)	0.0023 (19)	0.001 (2)
C2	0.030 (2)	0.031 (3)	0.041 (3)	−0.006 (2)	0.010 (2)	−0.005 (2)
C3	0.026 (2)	0.040 (3)	0.043 (3)	−0.006 (2)	0.006 (2)	−0.001 (2)
C4	0.032 (3)	0.045 (3)	0.039 (3)	−0.003 (2)	0.003 (2)	−0.006 (2)
C5	0.030 (3)	0.042 (3)	0.033 (3)	−0.001 (2)	0.012 (2)	0.001 (2)
C6	0.035 (3)	0.040 (3)	0.044 (3)	−0.004 (2)	0.001 (2)	0.008 (2)
C7	0.036 (3)	0.035 (3)	0.037 (3)	−0.003 (2)	0.007 (2)	0.006 (2)
C8	0.055 (3)	0.050 (3)	0.042 (3)	−0.020 (3)	0.016 (3)	−0.005 (3)
C9	0.039 (3)	0.030 (3)	0.043 (3)	−0.006 (2)	0.012 (2)	−0.004 (2)
C10	0.040 (3)	0.047 (3)	0.048 (3)	0.007 (2)	0.014 (2)	−0.010 (2)
C11	0.038 (3)	0.045 (3)	0.061 (3)	−0.001 (2)	0.015 (2)	−0.005 (3)
C12	0.044 (3)	0.035 (3)	0.041 (3)	−0.003 (2)	0.014 (2)	−0.005 (2)
C13	0.051 (3)	0.038 (3)	0.056 (3)	−0.011 (3)	0.002 (3)	0.007 (2)
C14	0.037 (3)	0.041 (3)	0.039 (3)	−0.008 (2)	0.002 (2)	0.003 (2)
C15	0.052 (3)	0.043 (3)	0.088 (5)	0.008 (2)	0.029 (3)	−0.001 (3)
C16	0.098 (2)	0.086 (2)	0.0683 (19)	−0.0274 (16)	−0.0119 (15)	0.0250 (15)
C17	0.068 (3)	0.074 (4)	0.046 (3)	−0.017 (3)	0.019 (3)	−0.012 (3)
C18	0.067 (4)	0.047 (3)	0.061 (4)	−0.002 (3)	0.029 (3)	−0.013 (3)
C19	0.071 (4)	0.045 (3)	0.067 (4)	−0.002 (3)	0.026 (3)	−0.012 (3)
C20	0.098 (2)	0.086 (2)	0.0683 (19)	−0.0274 (16)	−0.0119 (15)	0.0250 (15)
C21	0.098 (2)	0.086 (2)	0.0683 (19)	−0.0274 (16)	−0.0119 (15)	0.0250 (15)
C22	0.098 (2)	0.086 (2)	0.0683 (19)	−0.0274 (16)	−0.0119 (15)	0.0250 (15)
C23	0.098 (2)	0.086 (2)	0.0683 (19)	−0.0274 (16)	−0.0119 (15)	0.0250 (15)

Cl1—C9	1.728 (4)	C11—C15	1.368 (6)
Cl2—C8	1.729 (5)	C11—H11	0.9300
O1—C6	1.347 (5)	C12—C19	1.529 (6)
O1—C5	1.453 (5)	C12—C17	1.532 (6)
O2—C5	1.388 (5)	C13—C14	1.447 (6)
O2—H22	0.79 (4)	C13—C21	1.489 (6)
O3—C13	1.230 (5)	C15—C18	1.379 (6)
O4—C4	1.209 (5)	C15—H15	0.9300
C1—C3	1.510 (5)	C16—C20	1.485 (7)
C1—C5	1.532 (5)	C16—H16A	0.9700
C1—C4	1.538 (6)	C16—H16B	0.9700
C1—H1	0.9800	C17—H17A	0.9600
C2—C9	1.386 (6)	C17—H17B	0.9600
C2—C11	1.390 (5)	C17—H17C	0.9600
C2—C3	1.529 (6)	C18—H18	0.9300
C3—C14	1.511 (5)	C19—H19A	0.9600
C3—H3	0.9800	C19—H19B	0.9600
C4—C10	1.470 (6)	C19—H19C	0.9600
C5—C7	1.517 (5)	C20—C22	1.460 (7)
C6—C14	1.338 (5)	C20—C21	1.473 (7)
C6—C16	1.488 (6)	C20—C23	1.584 (8)
C7—C12	1.546 (5)	C21—H21A	0.9700
C7—H7A	0.9700	C21—H21B	0.9700
C7—H7B	0.9700	C22—H22A	0.9600
C8—C18	1.364 (6)	C22—H22B	0.9600
C8—C9	1.390 (6)	C22—H22C	0.9600
C10—C12	1.532 (5)	C23—H23A	0.9600
C10—H10A	0.9700	C23—H23B	0.9600
C10—H10B	0.9700	C23—H23C	0.9600
C6—O1—C5	119.0 (3)	C17—C12—C7	112.7 (3)
C5—O2—H22	106 (3)	O3—C13—C14	122.5 (4)
C3—C1—C5	114.1 (3)	O3—C13—C21	120.5 (4)
C3—C1—C4	112.4 (3)	C14—C13—C21	116.9 (4)
C5—C1—C4	109.2 (3)	C6—C14—C13	119.2 (4)
C3—C1—H1	106.9	C6—C14—C3	122.5 (4)
C5—C1—H1	106.9	C13—C14—C3	118.3 (4)
C4—C1—H1	106.9	C11—C15—C18	120.8 (5)
C9—C2—C11	117.9 (4)	C11—C15—H15	119.6
C9—C2—C3	120.7 (4)	C18—C15—H15	119.6
C11—C2—C3	121.3 (4)	C20—C16—C6	115.4 (4)
C1—C3—C14	108.4 (3)	C20—C16—H16A	108.4
C1—C3—C2	116.3 (3)	C6—C16—H16A	108.4
C14—C3—C2	112.5 (3)	C20—C16—H16B	108.4
C1—C3—H3	106.3	C6—C16—H16B	108.4
C14—C3—H3	106.3	H16A—C16—H16B	107.5
C2—C3—H3	106.3	C12—C17—H17A	109.5
O4—C4—C10	124.2 (4)	C12—C17—H17B	109.5
O4—C4—C1	119.9 (4)	H17A—C17—H17B	109.5
C10—C4—C1	115.8 (4)	C12—C17—H17C	109.5
O2—C5—O1	108.3 (3)	H17A—C17—H17C	109.5
O2—C5—C7	111.5 (3)	H17B—C17—H17C	109.5
O1—C5—C7	104.6 (3)	C8—C18—C15	119.0 (4)
O2—C5—C1	107.8 (3)	C8—C18—H18	120.5
O1—C5—C1	110.6 (3)	C15—C18—H18	120.5
C7—C5—C1	113.9 (3)	C12—C19—H19A	109.5
C14—C6—O1	124.7 (4)	C12—C19—H19B	109.5
C14—C6—C16	124.7 (4)	H19A—C19—H19B	109.5
O1—C6—C16	110.6 (4)	C12—C19—H19C	109.5
C5—C7—C12	117.2 (3)	H19A—C19—H19C	109.5
C5—C7—H7A	108.0	H19B—C19—H19C	109.5
C12—C7—H7A	108.0	C22—C20—C21	118.2 (5)
C5—C7—H7B	108.0	C22—C20—C16	114.6 (5)
C12—C7—H7B	108.0	C21—C20—C16	110.8 (5)
H7A—C7—H7B	107.2	C22—C20—C23	103.5 (5)
C18—C8—C9	120.8 (4)	C21—C20—C23	103.6 (5)
C18—C8—Cl2	118.5 (4)	C16—C20—C23	104.1 (5)
C9—C8—Cl2	120.6 (4)	C20—C21—C13	117.8 (5)
C2—C9—C8	120.4 (4)	C20—C21—H21A	107.9
C2—C9—Cl1	119.7 (3)	C13—C21—H21A	107.9
C8—C9—Cl1	119.8 (4)	C20—C21—H21B	107.9
C4—C10—C12	111.0 (4)	C13—C21—H21B	107.9
C4—C10—H10A	109.4	H21A—C21—H21B	107.2
C12—C10—H10A	109.4	C20—C22—H22A	109.5
C4—C10—H10B	109.4	C20—C22—H22B	109.5
C12—C10—H10B	109.4	H22A—C22—H22B	109.5
H10A—C10—H10B	108.0	C20—C22—H22C	109.5
C15—C11—C2	121.0 (4)	H22A—C22—H22C	109.5
C15—C11—H11	119.5	H22B—C22—H22C	109.5
C2—C11—H11	119.5	C20—C23—H23A	109.5
C19—C12—C10	110.3 (4)	C20—C23—H23B	109.5
C19—C12—C17	108.8 (4)	H23A—C23—H23B	109.5
C10—C12—C17	109.4 (4)	C20—C23—H23C	109.5
C19—C12—C7	108.0 (3)	H23A—C23—H23C	109.5
C10—C12—C7	107.7 (3)	H23B—C23—H23C	109.5
C5—C1—C3—C14	44.4 (5)	C1—C4—C10—C12	−61.1 (5)
C4—C1—C3—C14	−80.6 (4)	C9—C2—C11—C15	−1.1 (6)
C5—C1—C3—C2	−83.6 (4)	C3—C2—C11—C15	176.0 (4)
C4—C1—C3—C2	151.5 (3)	C4—C10—C12—C19	172.9 (4)
C9—C2—C3—C1	−73.9 (5)	C4—C10—C12—C17	−67.5 (5)
C11—C2—C3—C1	109.1 (4)	C4—C10—C12—C7	55.2 (5)
C9—C2—C3—C14	160.2 (4)	C5—C7—C12—C19	−169.0 (4)
C11—C2—C3—C14	−16.8 (5)	C5—C7—C12—C10	−49.8 (5)
C3—C1—C4—O4	3.8 (5)	C5—C7—C12—C17	70.8 (5)
C5—C1—C4—O4	−123.8 (4)	O1—C6—C14—C13	−175.9 (4)
C3—C1—C4—C10	−179.4 (3)	C16—C6—C14—C13	1.9 (7)
C5—C1—C4—C10	53.0 (5)	O1—C6—C14—C3	2.6 (7)
C6—O1—C5—O2	−84.3 (4)	C16—C6—C14—C3	−179.6 (5)
C6—O1—C5—C7	156.7 (3)	O3—C13—C14—C6	174.1 (4)
C6—O1—C5—C1	33.6 (5)	C21—C13—C14—C6	−8.4 (7)
C3—C1—C5—O2	65.9 (4)	O3—C13—C14—C3	−4.6 (7)
C4—C1—C5—O2	−167.5 (3)	C21—C13—C14—C3	173.0 (5)
C3—C1—C5—O1	−52.3 (5)	C1—C3—C14—C6	−20.3 (6)
C4—C1—C5—O1	74.3 (4)	C2—C3—C14—C6	109.8 (5)
C3—C1—C5—C7	−169.8 (3)	C1—C3—C14—C13	158.3 (4)
C4—C1—C5—C7	−43.2 (5)	C2—C3—C14—C13	−71.6 (5)
C5—O1—C6—C14	−9.9 (6)	C2—C11—C15—C18	2.2 (7)
C5—O1—C6—C16	172.1 (4)	C14—C6—C16—C20	−17.4 (9)
O2—C5—C7—C12	168.1 (3)	O1—C6—C16—C20	160.6 (5)
O1—C5—C7—C12	−75.0 (4)	C9—C8—C18—C15	1.4 (7)
C1—C5—C7—C12	45.9 (5)	Cl2—C8—C18—C15	−179.2 (4)
C11—C2—C9—C8	0.2 (6)	C11—C15—C18—C8	−2.3 (7)
C3—C2—C9—C8	−176.9 (4)	C6—C16—C20—C22	174.0 (6)
C11—C2—C9—Cl1	178.5 (3)	C6—C16—C20—C21	37.2 (8)
C3—C2—C9—Cl1	1.4 (5)	C6—C16—C20—C23	−73.6 (6)
C18—C8—C9—C2	−0.3 (7)	C22—C20—C21—C13	179.6 (5)
Cl2—C8—C9—C2	−179.8 (3)	C16—C20—C21—C13	−45.3 (8)
C18—C8—C9—Cl1	−178.6 (3)	C23—C20—C21—C13	65.8 (6)
Cl2—C8—C9—Cl1	1.9 (5)	O3—C13—C21—C20	−150.8 (5)
O4—C4—C10—C12	115.6 (5)	C14—C13—C21—C20	31.5 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H22···O3i	0.79 (4)	2.12 (4)	2.879 (4)	160 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H22⋯O3i	0.79 (4)	2.12 (4)	2.879 (4)	160 (5)

Symmetry code: (i) .