9-(4-Chloro­phen­yl)-4a-hy­droxy-4,4a,5,6,9,9a-hexa­hydro-3H-xanthene-1,8(2H,7H)-dione

Yang, Y.; Lu, W.; Lian, C.; Zhu, Y.

doi:10.1107/S1600536811031977

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2386

doi:10.1107/S1600536811031977

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9-(4-Chlorophenyl)-4a-hydroxy-4,4a,5,6,9,9a-hexahydro-3H-xanthene-1,8(2H,7H)-dione

Yan Yang,^a Weicheng Lu,^a Chaomei Lian ^a and Yulin Zhu ^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 6 July 2011; accepted 7 August 2011; online 27 August 2011)

In the title compound, C₁₉H₁₉ClO₄, the central fused ring and the attached cyclohexene ring adopt envelope conformations, while the cyclohexane ring adopts a chair conformation. The crystal packing is stabilized by O—H⋯O hydrogen bonds, which link the molecules into a chain along the b axis. Weak C—H⋯O bonds also occur.

Related literature

For the bilogical activity of xanthenes, see: Srividya et al. (1996 ); Wang et al., (2006 ); Kantevari et al. (2006 ); Reddy et al. (2009 ); Mehdi et al. (2011 ); Mo et al. (2010 ). For the synthesis of related compounds, see: Karade et al. (2007 ); Luna et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₉ClO₄
M_r = 346.79
Monoclinic, C 2/c
a = 25.076 (3) Å
b = 12.7715 (13) Å
c = 11.3825 (11) Å
β = 110.307 (1)°
V = 3418.7 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.30 × 0.15 × 0.15 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.931, T_max = 0.965
8674 measured reflections
3095 independent reflections
1984 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.111
S = 1.02
3095 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.82	1.84	2.654 (2)	172
C2—H10A⋯O1ⁱⁱ	0.97	2.52	3.199 (3)	127
C11—H6⋯O4ⁱⁱⁱ	0.93	2.56	3.483 (3)	174
C15—H4⋯O1^iv	0.93	2.58	3.452 (3)	156
C5—H17A⋯O3^iv	0.97	2.51	3.398 (3)	153
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[x, -y+1, z-{\script{1\over 2}}]$ .

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/S1600536811031977/aa2018sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811031977/aa2018Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811031977/aa2018Isup3.cml

checkCIF report

Comment top

Xanthenes are an important class of organic compounds which attract researchers by their spectroscopic and biological properties. Their derivatives had been tested to possess antitumoral, fungicidal, antiinflammatory and bactericidal properties. (Kantevari et al., 2006; Srividya et al., 1996; Wang et al., 2006; Reddy et al., 2009; Mehdi et al., 2011; Mo et al., 2010). A well established method used for the construction of xanthene unit was a tandem Michael reaction between 1,3-cyclohexanedione and benzaldehyde (Luna et al., 2009; Karade et al., 2007). The reaction between 1,3-cyclohexanedione and 4-chlorobenzaldehyde in the presence of thiourea and palladium(II) chloride proceeded to give the title compound with yield 91% (Fig. 1). The main structure of this compound (Fig. 2) is a derivated xanthenedione fused tricyclo ring with a hydroxyl group at its C4A position. The phenly ring is attached to a tricyclo ring at the C9 position. The central ring and the attached cyclohexene ring adopt an envelope conformation while the cyclohexane ring adopts a chair conformation. The crystal packing is stabilized by O—H···O hydrogen bond which links molecules into a chain along b axis. Weak C—H···O bonds were also found in this structure.

Related literature top

For the bilogical activity of xanthenes, see: Srividya et al. (1996); Wang et al., (2006); Kantevari et al. (2006); Reddy et al. (2009); Mehdi et al. (2011); Mo et al. (2010). For the synthesis of related compounds, see: Karade et al. (2007); Luna et al. (2009).

Experimental top

A mixture of 1,3-cyclohexanedione (1.12 g, 10 mmol), 4-chloro-benzaldehyde (0.7 g, 5 mmol), thiourea (0.76 g,10 mmol) and palladium (II) chloride (0.0020 mg) was refluxed in anhydrous acetonitrile (12 ml) at 373 K for 10 h. 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 anhydrous ethanol, and the filtrate was then dried under vacuum to yield the product in yield of 91% (Fig. 1). Single crystals of the title compound were obtained by slow evaporation from anhydrous ethanol at room temperature to yield colourless, block-shaped crystal.

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. Palladium(II) chloride catalyzed synthesis of the title compound.
	Fig. 2. A view of the title compound with the atom numbering scheme. Thermal displacement ellipsoids are drawn at the 50% probability level.

9-(4-Chlorophenyl)-4a-hydroxy-4,4a,5,6,9,9a-hexahydro-3H-xanthene- 1,8(2H,7H)-dione top

Crystal data top

C₁₉H₁₉ClO₄	F(000) = 1456
M_r = 346.79	D_x = 1.348 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1769 reflections
a = 25.076 (3) Å	θ = 2.4–20.3°
b = 12.7715 (13) Å	µ = 0.24 mm⁻¹
c = 11.3825 (11) Å	T = 298 K
β = 110.307 (1)°	Block, colourless
V = 3418.7 (6) Å³	0.30 × 0.15 × 0.15 mm
Z = 8

Data collection top

Bruker APEXII area-detector diffractometer	3095 independent reflections
Radiation source: fine-focus sealed tube	1984 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −30→30
T_min = 0.931, T_max = 0.965	k = −10→15
8674 measured reflections	l = −13→13

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) = 0.111	w = 1/[σ²(F_o²) + (0.0479P)² + 0.6651P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3095 reflections	Δρ_max = 0.17 e Å⁻³
219 parameters	Δρ_min = −0.22 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: 0.0007 (2)

Crystal data top

C₁₉H₁₉ClO₄	V = 3418.7 (6) Å³
M_r = 346.79	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 25.076 (3) Å	µ = 0.24 mm⁻¹
b = 12.7715 (13) Å	T = 298 K
c = 11.3825 (11) Å	0.30 × 0.15 × 0.15 mm
β = 110.307 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	3095 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1984 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.965	R_int = 0.035
8674 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.02	Δρ_max = 0.17 e Å⁻³
3095 reflections	Δρ_min = −0.22 e Å⁻³
219 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 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
Cl1	0.44721 (4)	0.02958 (6)	0.34171 (8)	0.1002 (3)
O4	0.31880 (6)	0.64755 (11)	0.14155 (12)	0.0466 (4)
C9	0.34321 (8)	0.45993 (15)	0.29866 (18)	0.0396 (5)
H7	0.3292	0.4676	0.3686	0.048*
C1	0.42884 (9)	0.56223 (17)	0.4411 (2)	0.0497 (6)
C8A	0.29282 (8)	0.47462 (17)	0.17790 (19)	0.0423 (5)
C10	0.36998 (8)	0.35209 (16)	0.30869 (18)	0.0396 (5)
C9A	0.38633 (8)	0.54699 (15)	0.30970 (18)	0.0406 (5)
H8	0.4075	0.5298	0.2543	0.049*
C4B	0.28472 (8)	0.56314 (18)	0.10889 (19)	0.0428 (5)
C15	0.39198 (10)	0.31582 (18)	0.2212 (2)	0.0536 (6)
H4	0.3903	0.3583	0.1537	0.064*
C4	0.39848 (10)	0.73910 (18)	0.2721 (2)	0.0558 (6)
H12A	0.3777	0.8040	0.2456	0.067*
H12B	0.4180	0.7233	0.2141	0.067*
C13	0.41858 (10)	0.15508 (18)	0.3296 (2)	0.0576 (7)
C5	0.23679 (9)	0.58061 (19)	−0.0116 (2)	0.0554 (6)
H17A	0.2504	0.6202	−0.0683	0.066*
H17B	0.2073	0.6213	0.0041	0.066*
C8	0.24755 (9)	0.39807 (19)	0.1437 (2)	0.0517 (6)
C11	0.37342 (10)	0.28731 (19)	0.4084 (2)	0.0541 (6)
H6	0.3593	0.3104	0.4695	0.065*
C12	0.39749 (10)	0.1886 (2)	0.4188 (2)	0.0616 (7)
H1	0.3993	0.1455	0.4860	0.074*
C2	0.47120 (10)	0.64849 (19)	0.4547 (3)	0.0695 (8)
H10A	0.4964	0.6297	0.4099	0.083*
H10B	0.4941	0.6568	0.5425	0.083*
C3	0.44180 (10)	0.75218 (19)	0.4037 (2)	0.0687 (8)
H11A	0.4228	0.7783	0.4589	0.082*
H11B	0.4701	0.8034	0.4020	0.082*
C14	0.41648 (11)	0.2179 (2)	0.2313 (2)	0.0613 (7)
H3	0.4314	0.1950	0.1715	0.074*
C7	0.19886 (10)	0.4081 (2)	0.0210 (2)	0.0743 (8)
H15A	0.1890	0.3390	−0.0155	0.089*
H15B	0.1660	0.4358	0.0370	0.089*
C6	0.21224 (11)	0.4780 (2)	−0.0717 (2)	0.0720 (8)
H16A	0.1778	0.4910	−0.1426	0.086*
H16B	0.2393	0.4433	−0.1024	0.086*
O1	0.42757 (7)	0.50975 (13)	0.52877 (15)	0.0629 (5)
O2	0.32669 (7)	0.66998 (12)	0.34916 (14)	0.0557 (4)
H2	0.3049	0.7193	0.3225	0.084*
O3	0.24715 (7)	0.32685 (13)	0.21722 (14)	0.0634 (5)
C4A	0.35751 (9)	0.65211 (16)	0.26941 (19)	0.0426 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1129 (7)	0.0477 (4)	0.1184 (7)	0.0259 (4)	0.0126 (5)	0.0036 (4)
O4	0.0448 (8)	0.0439 (9)	0.0435 (8)	−0.0013 (8)	0.0059 (7)	0.0069 (7)
C9	0.0383 (11)	0.0396 (12)	0.0388 (11)	−0.0018 (10)	0.0107 (9)	0.0008 (9)
C1	0.0461 (13)	0.0374 (13)	0.0534 (14)	0.0104 (11)	0.0018 (11)	−0.0065 (11)
C8A	0.0355 (11)	0.0448 (13)	0.0442 (12)	−0.0033 (10)	0.0106 (10)	0.0000 (11)
C10	0.0373 (11)	0.0370 (12)	0.0387 (11)	−0.0051 (10)	0.0057 (9)	−0.0002 (10)
C9A	0.0378 (11)	0.0357 (12)	0.0445 (12)	0.0006 (10)	0.0095 (10)	−0.0020 (10)
C4B	0.0361 (11)	0.0472 (14)	0.0434 (12)	−0.0042 (11)	0.0116 (10)	−0.0004 (10)
C15	0.0692 (15)	0.0434 (14)	0.0449 (13)	0.0043 (13)	0.0155 (12)	0.0025 (11)
C4	0.0543 (14)	0.0386 (13)	0.0649 (15)	−0.0021 (12)	0.0085 (12)	0.0008 (12)
C13	0.0535 (14)	0.0392 (14)	0.0655 (16)	0.0009 (12)	0.0020 (13)	−0.0013 (13)
C5	0.0433 (13)	0.0641 (16)	0.0502 (13)	0.0027 (12)	0.0053 (11)	0.0110 (12)
C8	0.0430 (13)	0.0560 (15)	0.0514 (13)	−0.0089 (12)	0.0104 (11)	−0.0007 (12)
C11	0.0572 (14)	0.0508 (15)	0.0541 (14)	−0.0007 (12)	0.0191 (12)	0.0088 (12)
C12	0.0616 (15)	0.0510 (15)	0.0655 (16)	−0.0008 (13)	0.0134 (14)	0.0198 (13)
C2	0.0512 (14)	0.0474 (15)	0.0855 (18)	−0.0023 (13)	−0.0070 (13)	−0.0072 (13)
C3	0.0606 (16)	0.0410 (14)	0.0834 (18)	−0.0055 (13)	−0.0015 (14)	−0.0059 (13)
C14	0.0728 (17)	0.0524 (16)	0.0549 (15)	0.0082 (14)	0.0173 (13)	−0.0064 (13)
C7	0.0525 (15)	0.081 (2)	0.0686 (17)	−0.0218 (15)	−0.0054 (13)	0.0077 (15)
C6	0.0617 (16)	0.080 (2)	0.0533 (15)	−0.0147 (15)	−0.0061 (13)	0.0034 (14)
O1	0.0702 (11)	0.0537 (11)	0.0493 (10)	0.0097 (9)	0.0012 (8)	−0.0029 (8)
O2	0.0574 (10)	0.0529 (11)	0.0557 (9)	0.0187 (8)	0.0182 (8)	0.0032 (8)
O3	0.0571 (10)	0.0657 (11)	0.0588 (10)	−0.0254 (9)	0.0089 (8)	0.0072 (9)
C4A	0.0409 (11)	0.0400 (13)	0.0417 (12)	0.0045 (10)	0.0079 (10)	0.0006 (10)

Geometric parameters (Å, º) top

Cl1—C13	1.742 (2)	C13—C14	1.362 (3)
O4—C4B	1.345 (2)	C13—C12	1.367 (3)
O4—C4A	1.443 (2)	C5—C6	1.507 (3)
C9—C10	1.519 (3)	C5—H17A	0.9700
C9—C8A	1.522 (3)	C5—H17B	0.9700
C9—C9A	1.525 (3)	C8—O3	1.238 (3)
C9—H7	0.9800	C8—C7	1.508 (3)
C1—O1	1.212 (3)	C11—C12	1.385 (3)
C1—C2	1.501 (3)	C11—H6	0.9300
C1—C9A	1.518 (3)	C12—H1	0.9300
C8A—C4B	1.351 (3)	C2—C3	1.529 (3)
C8A—C8	1.445 (3)	C2—H10A	0.9700
C10—C15	1.375 (3)	C2—H10B	0.9700
C10—C11	1.383 (3)	C3—H11A	0.9700
C9A—C4A	1.518 (3)	C3—H11B	0.9700
C9A—H8	0.9800	C14—H3	0.9300
C4B—C5	1.494 (3)	C7—C6	1.507 (3)
C15—C14	1.381 (3)	C7—H15A	0.9700
C15—H4	0.9300	C7—H15B	0.9700
C4—C4A	1.506 (3)	C6—H16A	0.9700
C4—C3	1.524 (3)	C6—H16B	0.9700
C4—H12A	0.9700	O2—C4A	1.400 (2)
C4—H12B	0.9700	O2—H2	0.8200

C4B—O4—C4A	116.83 (16)	O3—C8—C8A	120.3 (2)
C10—C9—C8A	112.73 (16)	O3—C8—C7	119.6 (2)
C10—C9—C9A	111.88 (16)	C8A—C8—C7	120.0 (2)
C8A—C9—C9A	109.10 (16)	C10—C11—C12	121.1 (2)
C10—C9—H7	107.6	C10—C11—H6	119.5
C8A—C9—H7	107.6	C12—C11—H6	119.5
C9A—C9—H7	107.6	C13—C12—C11	119.4 (2)
O1—C1—C2	122.8 (2)	C13—C12—H1	120.3
O1—C1—C9A	122.0 (2)	C11—C12—H1	120.3
C2—C1—C9A	115.2 (2)	C1—C2—C3	111.47 (19)
C4B—C8A—C8	117.64 (19)	C1—C2—H10A	109.3
C4B—C8A—C9	122.58 (19)	C3—C2—H10A	109.3
C8—C8A—C9	119.22 (18)	C1—C2—H10B	109.3
C15—C10—C11	117.8 (2)	C3—C2—H10B	109.3
C15—C10—C9	121.93 (19)	H10A—C2—H10B	108.0
C11—C10—C9	120.3 (2)	C4—C3—C2	111.3 (2)
C1—C9A—C4A	106.39 (16)	C4—C3—H11A	109.4
C1—C9A—C9	114.20 (18)	C2—C3—H11A	109.4
C4A—C9A—C9	111.72 (16)	C4—C3—H11B	109.4
C1—C9A—H8	108.1	C2—C3—H11B	109.4
C4A—C9A—H8	108.1	H11A—C3—H11B	108.0
C9—C9A—H8	108.1	C13—C14—C15	119.4 (2)
O4—C4B—C8A	123.84 (18)	C13—C14—H3	120.3
O4—C4B—C5	111.45 (19)	C15—C14—H3	120.3
C8A—C4B—C5	124.7 (2)	C6—C7—C8	113.2 (2)
C10—C15—C14	121.6 (2)	C6—C7—H15A	108.9
C10—C15—H4	119.2	C8—C7—H15A	108.9
C14—C15—H4	119.2	C6—C7—H15B	108.9
C4A—C4—C3	110.44 (19)	C8—C7—H15B	108.9
C4A—C4—H12A	109.6	H15A—C7—H15B	107.8
C3—C4—H12A	109.6	C7—C6—C5	110.6 (2)
C4A—C4—H12B	109.6	C7—C6—H16A	109.5
C3—C4—H12B	109.6	C5—C6—H16A	109.5
H12A—C4—H12B	108.1	C7—C6—H16B	109.5
C14—C13—C12	120.8 (2)	C5—C6—H16B	109.5
C14—C13—Cl1	120.3 (2)	H16A—C6—H16B	108.1
C12—C13—Cl1	119.0 (2)	C4A—O2—H2	109.5
C4B—C5—C6	111.0 (2)	O2—C4A—O4	109.33 (16)
C4B—C5—H17A	109.4	O2—C4A—C4	113.13 (18)
C6—C5—H17A	109.4	O4—C4A—C4	105.39 (16)
C4B—C5—H17B	109.4	O2—C4A—C9A	105.09 (17)
C6—C5—H17B	109.4	O4—C4A—C9A	110.61 (16)
H17A—C5—H17B	108.0	C4—C4A—C9A	113.34 (17)

C10—C9—C8A—C4B	−136.9 (2)	C9—C8A—C8—C7	−176.7 (2)
C9A—C9—C8A—C4B	−12.0 (3)	C15—C10—C11—C12	−0.9 (3)
C10—C9—C8A—C8	51.9 (3)	C9—C10—C11—C12	179.75 (19)
C9A—C9—C8A—C8	176.86 (18)	C14—C13—C12—C11	0.4 (4)
C8A—C9—C10—C15	59.2 (3)	Cl1—C13—C12—C11	−178.49 (17)
C9A—C9—C10—C15	−64.2 (2)	C10—C11—C12—C13	0.5 (4)
C8A—C9—C10—C11	−121.5 (2)	O1—C1—C2—C3	−124.8 (3)
C9A—C9—C10—C11	115.1 (2)	C9A—C1—C2—C3	53.5 (3)
O1—C1—C9A—C4A	122.9 (2)	C4A—C4—C3—C2	53.2 (3)
C2—C1—C9A—C4A	−55.4 (2)	C1—C2—C3—C4	−50.4 (3)
O1—C1—C9A—C9	−0.8 (3)	C12—C13—C14—C15	−0.9 (4)
C2—C1—C9A—C9	−179.16 (18)	Cl1—C13—C14—C15	177.94 (18)
C10—C9—C9A—C1	−72.7 (2)	C10—C15—C14—C13	0.5 (4)
C8A—C9—C9A—C1	161.85 (17)	O3—C8—C7—C6	−164.5 (2)
C10—C9—C9A—C4A	166.48 (17)	C8A—C8—C7—C6	18.8 (4)
C8A—C9—C9A—C4A	41.1 (2)	C8—C7—C6—C5	−49.6 (3)
C4A—O4—C4B—C8A	−14.8 (3)	C4B—C5—C6—C7	50.6 (3)
C4A—O4—C4B—C5	164.42 (18)	C4B—O4—C4A—O2	−70.6 (2)
C8—C8A—C4B—O4	168.96 (19)	C4B—O4—C4A—C4	167.55 (17)
C9—C8A—C4B—O4	−2.3 (3)	C4B—O4—C4A—C9A	44.7 (2)
C8—C8A—C4B—C5	−10.2 (3)	C3—C4—C4A—O2	60.3 (2)
C9—C8A—C4B—C5	178.6 (2)	C3—C4—C4A—O4	179.72 (19)
C11—C10—C15—C14	0.4 (3)	C3—C4—C4A—C9A	−59.2 (3)
C9—C10—C15—C14	179.70 (19)	C1—C9A—C4A—O2	−66.0 (2)
O4—C4B—C5—C6	158.98 (19)	C9—C9A—C4A—O2	59.2 (2)
C8A—C4B—C5—C6	−21.8 (3)	C1—C9A—C4A—O4	176.08 (17)
C4B—C8A—C8—O3	−164.9 (2)	C9—C9A—C4A—O4	−58.7 (2)
C9—C8A—C8—O3	6.7 (3)	C1—C9A—C4A—C4	58.0 (2)
C4B—C8A—C8—C7	11.8 (3)	C9—C9A—C4A—C4	−176.76 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.82	1.84	2.654 (2)	172
C2—H10A···O1ⁱⁱ	0.97	2.52	3.199 (3)	127
C11—H6···O4ⁱⁱⁱ	0.93	2.56	3.483 (3)	174
C15—H4···O1^iv	0.93	2.58	3.452 (3)	156
C5—H17A···O3^iv	0.97	2.51	3.398 (3)	153

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1, z+1/2; (iv) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₉ClO₄
M_r	346.79
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	25.076 (3), 12.7715 (13), 11.3825 (11)
β (°)	110.307 (1)
V (Å³)	3418.7 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.15 × 0.15

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.931, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	8674, 3095, 1984
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.111, 1.02
No. of reflections	3095
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.22

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···O3ⁱ	0.82	1.84	2.654 (2)	171.7
C2—H10A···O1ⁱⁱ	0.97	2.52	3.199 (3)	126.7
C11—H6···O4ⁱⁱⁱ	0.93	2.56	3.483 (3)	173.6
C15—H4···O1^iv	0.93	2.58	3.452 (3)	156.3
C5—H17A···O3^iv	0.97	2.51	3.398 (3)	152.7

Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, −y+1, z+1/2; (iv) x, −y+1, z−1/2.

Acknowledgements

The authors thank South China Normal University for financial support (grant SCNU G21096).

References

Bruker (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Volume 67| Part 9| September 2011| Page o2386

doi:10.1107/S1600536811031977

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

9-(4-Chloro­phen­yl)-4a-hy­dr­oxy-4,4a,5,6,9,9a-hexa­hydro-3H-xanthene-1,8(2H,7H)-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

9-(4-Chlorophenyl)-4a-hydroxy-4,4a,5,6,9,9a-hexahydro-3H-xanthene-1,8(2H,7H)-dione