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

In the title compound, C19H19ClO4, the di-hydro-pyran ring and the cyclo-hexane ring adopt a half-chair conformation and a chair conformation, respectively. The cyclo-hexene ring has an envelope conformation with the central CH2 C atom as the flap. This atom is disordered over two positions [site-occupancy ratio = 0.744 (12):0.256 (12)] above and below the mean plane formed by the other five atoms. In the crystal, O-H⋯O hydrogen bonds between hy-droxy and carbonyl groups link mol-ecules into chains propagating along [001].

Related literature

For the background, synthesis and activities of xanthenes, see: Knight & Stephens (1989 ▶); Srividya et al. (1996 ▶); Menchen et al. (2003 ▶); Reddy et al. (2009 ▶); Mehdi et al. (2011 ▶); Altieri et al.(2013 ▶). For related structures, see: Hua et al. (2006 ▶); Yang et al. (2011 ▶).

Experimental

Crystal data

C19H19ClO4

M = 346.79

Monoclinic,

a = 15.3099 (13) Å

b = 9.2815 (8) Å

c = 12.3216 (11) Å

β = 110.716 (1)°

V = 1637.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 291 K

0.25 × 0.23 × 0.18 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.94, T max = 0.96

12319 measured reflections

3207 independent reflections

2208 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.137

S = 1.00

3207 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814005297/xu5775sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814005297/xu5775Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814005297/xu5775Isup3.cml

CCDC reference: 990638

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H19ClO4	F(000) = 728
Mr = 346.79	Dx = 1.406 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2557 reflections
a = 15.3099 (13) Å	θ = 2.6–22.6°
b = 9.2815 (8) Å	µ = 0.25 mm−1
c = 12.3216 (11) Å	T = 291 K
β = 110.716 (1)°	Block, colorless
V = 1637.7 (2) Å3	0.25 × 0.23 × 0.18 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	3207 independent reflections
Radiation source: sealed tube	2208 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 26.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→18
Tmin = 0.94, Tmax = 0.96	k = −11→11
12319 measured reflections	l = −15→15

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0852P)2] where P = (Fo2 + 2Fc2)/3
3207 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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	Occ. (<1)
C1	0.36292 (16)	0.6212 (3)	0.22858 (19)	0.0374 (5)
C2	0.4586 (2)	0.5704 (3)	0.3045 (3)	0.0679 (9)
H2A	0.4519	0.5038	0.3618	0.082*
H2B	0.4865	0.5178	0.2569	0.082*
C3	0.5220 (3)	0.6854 (6)	0.3646 (6)	0.0557 (18)	0.744 (12)
H3A	0.5405	0.7363	0.3075	0.067*	0.744 (12)
H3B	0.5778	0.6441	0.4211	0.067*	0.744 (12)
C3'	0.4986 (10)	0.6331 (16)	0.4163 (11)	0.048 (4)	0.256 (12)
H3'A	0.5649	0.6240	0.4362	0.058*	0.256 (12)
H3'B	0.4820	0.5808	0.4733	0.058*	0.256 (12)
C4	0.48086 (16)	0.7929 (3)	0.4227 (2)	0.0474 (7)
H4A	0.5185	0.8798	0.4380	0.057*
H4B	0.4826	0.7543	0.4966	0.057*
C5	0.38240 (15)	0.8304 (2)	0.35106 (17)	0.0325 (5)
C6	0.32588 (14)	0.7506 (2)	0.26163 (17)	0.0304 (5)
C7	0.22743 (14)	0.7965 (2)	0.19183 (17)	0.0294 (5)
H7A	0.2224	0.7950	0.1103	0.035*
C8	0.21218 (14)	0.9542 (2)	0.21988 (16)	0.0287 (5)
H8A	0.1447	0.9677	0.1986	0.034*
C9	0.24489 (16)	1.0626 (3)	0.14999 (18)	0.0368 (5)
C10	0.2394 (2)	1.2177 (3)	0.1799 (2)	0.0475 (6)
H10A	0.1745	1.2456	0.1591	0.057*
H10B	0.2671	1.2769	0.1357	0.057*
C11	0.29051 (17)	1.2435 (3)	0.3093 (2)	0.0408 (6)
H11A	0.3568	1.2265	0.3284	0.049*
H11B	0.2822	1.3429	0.3278	0.049*
C12	0.25337 (16)	1.1442 (3)	0.38055 (19)	0.0374 (6)
H12A	0.2898	1.1578	0.4621	0.045*
H12B	0.1893	1.1705	0.3685	0.045*
C13	0.25672 (14)	0.9869 (2)	0.35002 (17)	0.0296 (5)
C14	0.15332 (15)	0.6935 (2)	0.20126 (18)	0.0308 (5)
C15	0.06507 (16)	0.6870 (2)	0.11488 (19)	0.0364 (5)
C16	−0.00219 (17)	0.5888 (3)	0.1178 (2)	0.0461 (6)
H16A	−0.0601	0.5866	0.0582	0.055*
C17	0.01752 (18)	0.4942 (3)	0.2097 (2)	0.0491 (7)
H17A	−0.0268	0.4268	0.2119	0.059*
C18	0.10288 (18)	0.5000 (3)	0.2982 (2)	0.0450 (6)
H18A	0.1157	0.4378	0.3611	0.054*
C19	0.17003 (16)	0.5983 (2)	0.29409 (19)	0.0364 (5)
H19A	0.2275	0.6007	0.3545	0.044*
Cl1	0.03711 (4)	0.80536 (8)	−0.00262 (5)	0.0547 (2)
O1	0.35645 (10)	0.95441 (16)	0.38789 (12)	0.0361 (4)
O2	0.31864 (12)	0.55190 (18)	0.14146 (13)	0.0472 (5)
O3	0.27329 (14)	1.0251 (2)	0.07442 (15)	0.0588 (5)
O4	0.21588 (11)	0.89704 (16)	0.40837 (12)	0.0387 (4)
H4O	0.2496	0.8920	0.4769	0.058*

	U11	U22	U33	U12	U13	U23
C1	0.0396 (13)	0.0346 (13)	0.0383 (12)	0.0004 (10)	0.0139 (10)	−0.0021 (10)
C2	0.0515 (18)	0.0584 (19)	0.078 (2)	0.0237 (15)	0.0032 (15)	−0.0164 (16)
C3	0.028 (2)	0.049 (3)	0.082 (4)	0.0068 (18)	0.009 (2)	−0.012 (3)
C3'	0.036 (7)	0.058 (8)	0.040 (6)	0.010 (6)	0.001 (5)	0.010 (5)
C4	0.0312 (13)	0.0437 (16)	0.0537 (14)	0.0042 (11)	−0.0020 (11)	−0.0068 (12)
C5	0.0302 (12)	0.0337 (13)	0.0322 (11)	0.0010 (10)	0.0093 (9)	−0.0022 (9)
C6	0.0281 (11)	0.0311 (12)	0.0308 (10)	−0.0014 (9)	0.0089 (9)	−0.0009 (9)
C7	0.0275 (11)	0.0328 (12)	0.0254 (10)	−0.0014 (9)	0.0064 (8)	−0.0030 (8)
C8	0.0258 (11)	0.0289 (11)	0.0292 (10)	−0.0023 (9)	0.0070 (8)	−0.0001 (9)
C9	0.0373 (13)	0.0400 (14)	0.0280 (11)	−0.0077 (10)	0.0052 (9)	0.0007 (9)
C10	0.0578 (16)	0.0362 (14)	0.0457 (14)	−0.0037 (12)	0.0149 (12)	0.0069 (11)
C11	0.0434 (14)	0.0301 (13)	0.0463 (13)	−0.0036 (11)	0.0129 (11)	−0.0038 (10)
C12	0.0381 (13)	0.0355 (13)	0.0388 (12)	0.0011 (10)	0.0138 (10)	−0.0054 (10)
C13	0.0281 (11)	0.0308 (12)	0.0298 (10)	−0.0006 (9)	0.0101 (9)	−0.0010 (9)
C14	0.0290 (11)	0.0291 (12)	0.0334 (10)	−0.0005 (9)	0.0098 (9)	−0.0080 (9)
C15	0.0334 (12)	0.0380 (14)	0.0353 (11)	−0.0004 (10)	0.0092 (9)	−0.0054 (10)
C16	0.0298 (13)	0.0542 (17)	0.0524 (14)	−0.0094 (12)	0.0123 (11)	−0.0158 (13)
C17	0.0439 (15)	0.0463 (16)	0.0654 (17)	−0.0161 (12)	0.0298 (13)	−0.0139 (13)
C18	0.0543 (16)	0.0380 (15)	0.0505 (14)	−0.0036 (12)	0.0281 (12)	−0.0005 (11)
C19	0.0358 (12)	0.0347 (13)	0.0381 (12)	−0.0038 (10)	0.0122 (10)	−0.0025 (10)
Cl1	0.0444 (4)	0.0587 (5)	0.0442 (4)	−0.0027 (3)	−0.0052 (3)	0.0053 (3)
O1	0.0286 (8)	0.0362 (9)	0.0366 (8)	0.0016 (7)	0.0031 (6)	−0.0094 (7)
O2	0.0585 (11)	0.0397 (10)	0.0387 (9)	0.0032 (8)	0.0114 (8)	−0.0113 (8)
O3	0.0818 (14)	0.0590 (12)	0.0456 (10)	−0.0228 (11)	0.0348 (10)	−0.0083 (9)
O4	0.0442 (9)	0.0397 (10)	0.0322 (8)	−0.0043 (8)	0.0136 (7)	0.0019 (7)

C1—O2	1.229 (3)	C8—H8A	0.9800
C1—C6	1.447 (3)	C9—O3	1.210 (3)
C1—C2	1.509 (3)	C9—C10	1.495 (3)
C2—C3'	1.419 (11)	C10—C11	1.526 (3)
C2—C3	1.456 (5)	C10—H10A	0.9700
C2—H2A	0.9700	C10—H10B	0.9700
C2—H2B	0.9700	C11—C12	1.515 (3)
C3—C4	1.490 (5)	C11—H11A	0.9700
C3—H3A	0.9700	C11—H11B	0.9700
C3—H3B	0.9700	C12—C13	1.513 (3)
C3—H3'A	1.0608	C12—H12A	0.9700
C3'—C4	1.514 (13)	C12—H12B	0.9700
C3'—H3B	1.1976	C13—O4	1.386 (2)
C3'—H3'A	0.9601	C13—O1	1.461 (2)
C3'—H3'B	0.9599	C14—C15	1.395 (3)
C4—C5	1.494 (3)	C14—C19	1.396 (3)
C4—H4A	0.9700	C15—C16	1.385 (3)
C4—H4B	0.9700	C15—Cl1	1.746 (2)
C5—O1	1.348 (3)	C16—C17	1.380 (4)
C5—C6	1.355 (3)	C16—H16A	0.9300
C6—C7	1.509 (3)	C17—C18	1.375 (4)
C7—C14	1.519 (3)	C17—H17A	0.9300
C7—C8	1.541 (3)	C18—C19	1.389 (3)
C7—H7A	0.9800	C18—H18A	0.9300
C8—C9	1.520 (3)	C19—H19A	0.9300
C8—C13	1.535 (3)	O4—H4O	0.8200
O2—C1—C6	122.0 (2)	C8—C7—H7A	106.3
O2—C1—C2	119.5 (2)	C9—C8—C13	110.33 (17)
C6—C1—C2	118.4 (2)	C9—C8—C7	113.29 (17)
C3'—C2—C3	39.2 (6)	C13—C8—C7	112.07 (17)
C3'—C2—C1	117.7 (5)	C9—C8—H8A	106.9
C3—C2—C1	114.3 (3)	C13—C8—H8A	106.9
C3'—C2—H2A	71.1	C7—C8—H8A	106.9
C3—C2—H2A	108.7	O3—C9—C10	122.2 (2)
C1—C2—H2A	108.7	O3—C9—C8	121.7 (2)
C3'—C2—H2B	131.5	C10—C9—C8	116.0 (2)
C3—C2—H2B	108.7	C9—C10—C11	110.9 (2)
C1—C2—H2B	108.7	C9—C10—H10A	109.5
H2A—C2—H2B	107.6	C11—C10—H10A	109.5
C2—C3—C4	114.6 (4)	C9—C10—H10B	109.5
C2—C3—H3A	107.5	C11—C10—H10B	109.5
C4—C3—H3A	107.7	H10A—C10—H10B	108.1
C2—C3—H3B	109.5	C12—C11—C10	110.56 (19)
C4—C3—H3B	109.6	C12—C11—H11A	109.5
H3A—C3—H3B	107.6	C10—C11—H11A	109.5
C2—C3—H3'A	97.7	C12—C11—H11B	109.5
C4—C3—H3'A	101.8	C10—C11—H11B	109.5
H3A—C3—H3'A	127.7	H11A—C11—H11B	108.1
H3B—C3—H3'A	20.2	C13—C12—C11	112.95 (18)
C2—C3'—C4	115.4 (8)	C13—C12—H12A	109.0
C2—C3'—H3B	99.5	C11—C12—H12A	109.0
C4—C3'—H3B	96.4	C13—C12—H12B	109.0
C2—C3'—H3'A	105.4	C11—C12—H12B	109.0
C4—C3'—H3'A	105.5	H12A—C12—H12B	107.8
H3B—C3'—H3'A	15.0	O4—C13—O1	108.80 (16)
C2—C3'—H3'B	111.6	O4—C13—C12	112.99 (17)
C4—C3'—H3'B	111.0	O1—C13—C12	104.07 (16)
H3B—C3'—H3'B	122.2	O4—C13—C8	107.92 (16)
H3'A—C3'—H3'B	107.3	O1—C13—C8	108.71 (16)
C3—C4—C5	112.5 (2)	C12—C13—C8	114.14 (18)
C3—C4—C3'	37.4 (5)	C15—C14—C19	116.4 (2)
C5—C4—C3'	111.1 (5)	C15—C14—C7	121.16 (19)
C3—C4—H4A	109.1	C19—C14—C7	122.39 (19)
C5—C4—H4A	109.1	C16—C15—C14	122.5 (2)
C3'—C4—H4A	136.0	C16—C15—Cl1	117.97 (18)
C3—C4—H4B	109.1	C14—C15—Cl1	119.50 (17)
C5—C4—H4B	109.1	C17—C16—C15	119.4 (2)
C3'—C4—H4B	75.0	C17—C16—H16A	120.3
H4A—C4—H4B	107.8	C15—C16—H16A	120.3
O1—C5—C6	124.11 (19)	C18—C17—C16	119.8 (2)
O1—C5—C4	110.88 (18)	C18—C17—H17A	120.1
C6—C5—C4	125.0 (2)	C16—C17—H17A	120.1
C5—C6—C1	118.8 (2)	C17—C18—C19	120.3 (2)
C5—C6—C7	122.1 (2)	C17—C18—H18A	119.9
C1—C6—C7	119.07 (18)	C19—C18—H18A	119.9
C6—C7—C14	113.68 (17)	C18—C19—C14	121.5 (2)
C6—C7—C8	109.90 (16)	C18—C19—H19A	119.2
C14—C7—C8	113.82 (17)	C14—C19—H19A	119.2
C6—C7—H7A	106.3	C5—O1—C13	117.90 (16)
C14—C7—H7A	106.3	C13—O4—H4O	109.5
O2—C1—C2—C3'	−166.3 (10)	C7—C8—C9—C10	−175.13 (18)
C6—C1—C2—C3'	13.3 (10)	O3—C9—C10—C11	−126.3 (2)
O2—C1—C2—C3	150.0 (4)	C8—C9—C10—C11	53.9 (3)
C6—C1—C2—C3	−30.3 (5)	C9—C10—C11—C12	−55.0 (3)
C3'—C2—C3—C4	−57.7 (7)	C10—C11—C12—C13	54.7 (3)
C1—C2—C3—C4	46.9 (7)	C11—C12—C13—O4	−175.08 (17)
C3—C2—C3'—C4	56.8 (10)	C11—C12—C13—O1	67.1 (2)
C1—C2—C3'—C4	−38.5 (17)	C11—C12—C13—C8	−51.3 (2)
C2—C3—C4—C5	−40.4 (7)	C9—C8—C13—O4	172.60 (17)
C2—C3—C4—C3'	55.3 (7)	C7—C8—C13—O4	−60.2 (2)
C2—C3'—C4—C3	−58.2 (10)	C9—C8—C13—O1	−69.5 (2)
C2—C3'—C4—C5	41.6 (15)	C7—C8—C13—O1	57.7 (2)
C3—C4—C5—O1	−162.2 (4)	C9—C8—C13—C12	46.1 (2)
C3'—C4—C5—O1	157.5 (8)	C7—C8—C13—C12	173.36 (17)
C3—C4—C5—C6	18.4 (5)	C6—C7—C14—C15	−156.35 (19)
C3'—C4—C5—C6	−22.0 (9)	C8—C7—C14—C15	76.8 (2)
O1—C5—C6—C1	178.4 (2)	C6—C7—C14—C19	21.9 (3)
C4—C5—C6—C1	−2.2 (3)	C8—C7—C14—C19	−105.0 (2)
O1—C5—C6—C7	1.6 (3)	C19—C14—C15—C16	−2.0 (3)
C4—C5—C6—C7	−179.0 (2)	C7—C14—C15—C16	176.3 (2)
O2—C1—C6—C5	−172.6 (2)	C19—C14—C15—Cl1	178.38 (16)
C2—C1—C6—C5	7.7 (3)	C7—C14—C15—Cl1	−3.3 (3)
O2—C1—C6—C7	4.3 (3)	C14—C15—C16—C17	0.7 (3)
C2—C1—C6—C7	−175.3 (2)	Cl1—C15—C16—C17	−179.66 (19)
C5—C6—C7—C14	−116.6 (2)	C15—C16—C17—C18	1.1 (4)
C1—C6—C7—C14	66.6 (2)	C16—C17—C18—C19	−1.5 (4)
C5—C6—C7—C8	12.3 (3)	C17—C18—C19—C14	0.1 (3)
C1—C6—C7—C8	−164.54 (18)	C15—C14—C19—C18	1.6 (3)
C6—C7—C8—C9	84.2 (2)	C7—C14—C19—C18	−176.7 (2)
C14—C7—C8—C9	−147.02 (17)	C6—C5—O1—C13	15.9 (3)
C6—C7—C8—C13	−41.5 (2)	C4—C5—O1—C13	−163.57 (18)
C14—C7—C8—C13	87.3 (2)	O4—C13—O1—C5	72.7 (2)
C13—C8—C9—O3	131.7 (2)	C12—C13—O1—C5	−166.63 (17)
C7—C8—C9—O3	5.1 (3)	C8—C13—O1—C5	−44.6 (2)
C13—C8—C9—C10	−48.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O2i	0.82	2.00	2.784 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O2i	0.82	2.00	2.784 (2)	161

Symmetry code: (i) .