9-(4-Chloro-phen-yl)-4a-hy-droxy-4,4a,5,6,9,9a-hexa-hydro-3H-xanthene-1,8(2H,7H)-dione.

In the title compound, C(19)H(19)ClO(4), the central fused ring and the attached cyclo-hexene ring adopt envelope conformations, while the cyclo-hexane ring adopts a chair conformation. The crystal packing is stabilized by O-H⋯O hydrogen bonds, which link the mol-ecules 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 = 346.79

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.02

3095 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031977/aa2018sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811031977/aa2018Isup3.cml

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

C19H19ClO4	F(000) = 1456
Mr = 346.79	Dx = 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

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

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(Fo2) + (0.0479P)2 + 0.6651P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
3095 reflections	Δρmax = 0.17 e Å−3
219 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O1iv	0.93	2.58	3.452 (3)	156.
C5—H17A···O3iv	0.97	2.51	3.398 (3)	153.

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⋯O1iv	0.93	2.58	3.452 (3)	156
C5—H17A⋯O3iv	0.97	2.51	3.398 (3)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .