14-Bromo-12-chloro-2,16-dioxa-penta-cyclo-[7.7.5.0(1,21).0(3,8).0(10,15)]henicosa-3(8),10,12,14-tetra-ene-7,20-dione.

In the title compound, C19H16BrClO4, both the fused xanthene rings and one of the cyclo-hexane rings adopt envelope conformations, while the other cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming infinite chains running along [10-1] incorporating R 2 (2)(16) ring motifs. In addition, C-H⋯π inter-actions and weak π-π stacking inter-actions [centroid-centroid distance = 3.768 (3) Å] help to consolidate the packing.

Related literature

For similar structures, see: Mohamed et al. (2012b ▶); Lu et al. (2011 ▶); Abdelhamid et al. (2011 ▶). For the bioactiviy of xanthenones, see: Mohamed et al. (2012a ▶); Gobbi et al. (2006 ▶); Na (2009 ▶). For ring conformations, see: Cremer and Pople (1975 ▶).

Experimental

Crystal data

C19H16BrClO4

M = 423.67

Monoclinic,

a = 10.2741 (6) Å

b = 10.2800 (6) Å

c = 15.8581 (8) Å

β = 102.073 (5)°

V = 1637.85 (16) Å3

Z = 4

Mo Kα radiation

μ = 2.70 mm−1

T = 123 K

0.25 × 0.20 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.529, T max = 0.616

7243 measured reflections

3516 independent reflections

2547 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.134

S = 1.04

3516 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.79 e Å−3

Δρmin = −0.73 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813010374/hb7072sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813010374/hb7072Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813010374/hb7072Isup3.cml

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

C19H16BrClO4	F(000) = 856
Mr = 423.67	Dx = 1.718 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2011 reflections
a = 10.2741 (6) Å	θ = 3.0–28.8°
b = 10.2800 (6) Å	µ = 2.70 mm−1
c = 15.8581 (8) Å	T = 123 K
β = 102.073 (5)°	Block, colourless
V = 1637.85 (16) Å3	0.25 × 0.20 × 0.18 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	3516 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2547 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 16.0727 pixels mm-1	θmax = 27.0°, θmin = 3.3°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −11→12
Tmin = 0.529, Tmax = 0.616	l = −19→20
7243 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0456P)2 + 3.8105P] where P = (Fo2 + 2Fc2)/3
3516 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.79 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Br1	0.83070 (5)	0.65176 (6)	0.51190 (3)	0.0317 (2)
Cl1	0.48771 (12)	0.24296 (11)	0.40547 (8)	0.0239 (4)
O1	0.5310 (3)	0.6514 (3)	0.1626 (2)	0.0248 (11)
O2	0.4643 (3)	0.9536 (3)	0.37446 (19)	0.0204 (10)
O3	0.1281 (3)	0.6340 (4)	0.3173 (2)	0.0309 (12)
O4	0.6260 (3)	0.7948 (3)	0.3862 (2)	0.0222 (10)
C1	0.6710 (4)	0.5856 (5)	0.4453 (3)	0.0192 (14)
C2	0.6398 (5)	0.4564 (5)	0.4527 (3)	0.0209 (16)
C3	0.5230 (5)	0.4094 (4)	0.4018 (3)	0.0180 (14)
C4	0.4377 (5)	0.4900 (5)	0.3470 (3)	0.0199 (16)
C5	0.4683 (5)	0.6205 (4)	0.3418 (3)	0.0174 (14)
C6	0.5875 (4)	0.6689 (4)	0.3903 (3)	0.0165 (14)
C7	0.5465 (4)	0.8852 (5)	0.3268 (3)	0.0186 (14)
C8	0.6430 (5)	0.9822 (5)	0.3029 (3)	0.0224 (16)
C9	0.7320 (5)	0.9167 (5)	0.2502 (3)	0.0258 (17)
C10	0.6512 (5)	0.8501 (5)	0.1700 (3)	0.0273 (17)
C11	0.5501 (5)	0.7597 (5)	0.1918 (3)	0.0188 (14)
C12	0.4649 (4)	0.8147 (4)	0.2507 (3)	0.0173 (12)
C13	0.3782 (4)	0.7170 (5)	0.2854 (3)	0.0189 (14)
C14	0.2961 (4)	0.7914 (5)	0.3381 (3)	0.0185 (14)
C15	0.1663 (5)	0.7408 (5)	0.3456 (3)	0.0218 (14)
C16	0.0825 (5)	0.8278 (5)	0.3889 (3)	0.0297 (17)
C17	0.1648 (5)	0.9056 (5)	0.4622 (3)	0.0293 (17)
C18	0.2719 (5)	0.9826 (5)	0.4319 (3)	0.0226 (16)
C19	0.3432 (5)	0.9016 (5)	0.3786 (3)	0.0185 (14)
H2	0.69700	0.40090	0.49180	0.0250*
H4	0.35780	0.45610	0.31280	0.0240*
H8A	0.69840	1.01970	0.35590	0.0270*
H8B	0.59310	1.05390	0.26900	0.0270*
H9A	0.78860	0.85130	0.28640	0.0310*
H9B	0.79120	0.98260	0.23250	0.0310*
H10A	0.60600	0.91700	0.12930	0.0320*
H10B	0.71220	0.80100	0.14090	0.0320*
H12	0.40380	0.88020	0.21640	0.0210*
H13	0.31860	0.67080	0.23660	0.0220*
H16A	0.01760	0.77390	0.41160	0.0360*
H16B	0.03170	0.88840	0.34570	0.0360*
H17A	0.10610	0.96580	0.48570	0.0350*
H17B	0.20660	0.84580	0.50900	0.0350*
H18A	0.23100	1.05820	0.39760	0.0270*
H18B	0.33640	1.01600	0.48260	0.0270*

	U11	U22	U33	U12	U13	U23
Br1	0.0228 (3)	0.0413 (4)	0.0276 (3)	−0.0031 (2)	−0.0026 (2)	0.0050 (3)
Cl1	0.0344 (7)	0.0103 (6)	0.0300 (6)	−0.0019 (5)	0.0134 (5)	−0.0010 (5)
O1	0.0262 (19)	0.026 (2)	0.0228 (17)	−0.0010 (16)	0.0067 (14)	−0.0059 (16)
O2	0.0222 (18)	0.0182 (18)	0.0219 (17)	−0.0016 (14)	0.0075 (14)	−0.0044 (14)
O3	0.024 (2)	0.034 (2)	0.036 (2)	−0.0078 (17)	0.0092 (16)	−0.0022 (18)
O4	0.0228 (18)	0.0182 (18)	0.0230 (17)	−0.0041 (14)	−0.0012 (14)	0.0016 (14)
C1	0.014 (2)	0.025 (3)	0.020 (2)	−0.002 (2)	0.0066 (19)	−0.001 (2)
C2	0.024 (3)	0.024 (3)	0.018 (2)	0.009 (2)	0.012 (2)	0.004 (2)
C3	0.026 (3)	0.008 (2)	0.023 (2)	0.0001 (19)	0.012 (2)	0.0006 (19)
C4	0.020 (3)	0.020 (3)	0.023 (2)	−0.005 (2)	0.012 (2)	−0.005 (2)
C5	0.020 (2)	0.019 (3)	0.016 (2)	0.0013 (19)	0.0102 (19)	−0.0002 (19)
C6	0.016 (2)	0.018 (3)	0.018 (2)	−0.0022 (19)	0.0096 (18)	−0.003 (2)
C7	0.017 (2)	0.016 (3)	0.023 (2)	−0.0007 (19)	0.005 (2)	0.001 (2)
C8	0.020 (3)	0.022 (3)	0.024 (2)	−0.006 (2)	0.002 (2)	−0.004 (2)
C9	0.019 (3)	0.031 (3)	0.029 (3)	−0.005 (2)	0.009 (2)	−0.002 (2)
C10	0.028 (3)	0.028 (3)	0.026 (3)	−0.004 (2)	0.006 (2)	−0.002 (2)
C11	0.018 (2)	0.023 (3)	0.014 (2)	0.004 (2)	0.0001 (18)	0.000 (2)
C12	0.019 (2)	0.016 (2)	0.017 (2)	−0.0011 (19)	0.0037 (18)	0.0021 (19)
C13	0.020 (2)	0.017 (3)	0.019 (2)	−0.002 (2)	0.0026 (19)	0.0011 (19)
C14	0.020 (2)	0.023 (3)	0.013 (2)	0.005 (2)	0.0043 (18)	0.003 (2)
C15	0.017 (2)	0.027 (3)	0.020 (2)	−0.002 (2)	0.0009 (19)	0.007 (2)
C16	0.015 (3)	0.039 (3)	0.037 (3)	0.000 (2)	0.010 (2)	0.008 (3)
C17	0.031 (3)	0.032 (3)	0.028 (3)	0.007 (2)	0.013 (2)	0.006 (2)
C18	0.024 (3)	0.024 (3)	0.022 (2)	0.004 (2)	0.010 (2)	0.000 (2)
C19	0.018 (2)	0.021 (3)	0.017 (2)	0.003 (2)	0.0045 (19)	0.005 (2)

Br1—C1	1.883 (5)	C14—C15	1.459 (7)
Cl1—C3	1.753 (4)	C14—C19	1.342 (7)
O1—C11	1.206 (6)	C15—C16	1.503 (7)
O2—C7	1.430 (6)	C16—C17	1.515 (7)
O2—C19	1.368 (6)	C17—C18	1.513 (7)
O3—C15	1.220 (6)	C18—C19	1.484 (7)
O4—C6	1.359 (5)	C2—H2	0.9500
O4—C7	1.448 (6)	C4—H4	0.9500
C1—C2	1.377 (7)	C8—H8A	0.9900
C1—C6	1.385 (6)	C8—H8B	0.9900
C2—C3	1.386 (7)	C9—H9A	0.9900
C3—C4	1.375 (7)	C9—H9B	0.9900
C4—C5	1.384 (7)	C10—H10A	0.9900
C5—C6	1.395 (7)	C10—H10B	0.9900
C5—C13	1.515 (7)	C12—H12	1.0000
C7—C8	1.509 (7)	C13—H13	1.0000
C7—C12	1.504 (6)	C16—H16A	0.9900
C8—C9	1.519 (7)	C16—H16B	0.9900
C9—C10	1.528 (7)	C17—H17A	0.9900
C10—C11	1.487 (7)	C17—H17B	0.9900
C11—C12	1.517 (7)	C18—H18A	0.9900
C12—C13	1.520 (6)	C18—H18B	0.9900
C13—C14	1.513 (7)
C7—O2—C19	118.5 (4)	O2—C19—C14	123.2 (4)
C6—O4—C7	120.8 (3)	O2—C19—C18	111.7 (4)
Br1—C1—C2	119.5 (4)	C14—C19—C18	125.1 (5)
Br1—C1—C6	118.8 (4)	C1—C2—H2	121.00
C2—C1—C6	121.7 (4)	C3—C2—H2	121.00
C1—C2—C3	118.4 (4)	C3—C4—H4	120.00
Cl1—C3—C2	118.8 (4)	C5—C4—H4	120.00
Cl1—C3—C4	120.0 (4)	C7—C8—H8A	110.00
C2—C3—C4	121.2 (4)	C7—C8—H8B	110.00
C3—C4—C5	119.9 (5)	C9—C8—H8A	110.00
C4—C5—C6	119.8 (4)	C9—C8—H8B	110.00
C4—C5—C13	123.5 (4)	H8A—C8—H8B	108.00
C6—C5—C13	116.7 (4)	C8—C9—H9A	109.00
O4—C6—C1	118.1 (4)	C8—C9—H9B	109.00
O4—C6—C5	123.0 (4)	C10—C9—H9A	109.00
C1—C6—C5	118.9 (4)	C10—C9—H9B	109.00
O2—C7—O4	106.7 (3)	H9A—C9—H9B	108.00
O2—C7—C8	107.4 (4)	C9—C10—H10A	109.00
O2—C7—C12	111.7 (3)	C9—C10—H10B	109.00
O4—C7—C8	106.1 (3)	C11—C10—H10A	109.00
O4—C7—C12	110.9 (4)	C11—C10—H10B	109.00
C8—C7—C12	113.7 (4)	H10A—C10—H10B	108.00
C7—C8—C9	110.4 (4)	C7—C12—H12	107.00
C8—C9—C10	111.8 (4)	C11—C12—H12	107.00
C9—C10—C11	111.8 (4)	C13—C12—H12	107.00
O1—C11—C10	123.6 (5)	C5—C13—H13	110.00
O1—C11—C12	120.8 (4)	C12—C13—H13	110.00
C10—C11—C12	115.6 (4)	C14—C13—H13	110.00
C7—C12—C11	112.2 (4)	C15—C16—H16A	109.00
C7—C12—C13	107.4 (4)	C15—C16—H16B	109.00
C11—C12—C13	115.7 (4)	C17—C16—H16A	109.00
C5—C13—C12	108.3 (4)	C17—C16—H16B	109.00
C5—C13—C14	110.3 (4)	H16A—C16—H16B	108.00
C12—C13—C14	107.6 (4)	C16—C17—H17A	109.00
C13—C14—C15	119.3 (4)	C16—C17—H17B	109.00
C13—C14—C19	120.3 (4)	C18—C17—H17A	109.00
C15—C14—C19	120.4 (4)	C18—C17—H17B	109.00
O3—C15—C14	121.3 (5)	H17A—C17—H17B	108.00
O3—C15—C16	122.2 (5)	C17—C18—H18A	109.00
C14—C15—C16	116.5 (4)	C17—C18—H18B	109.00
C15—C16—C17	112.6 (4)	C19—C18—H18A	109.00
C16—C17—C18	111.0 (4)	C19—C18—H18B	109.00
C17—C18—C19	111.5 (4)	H18A—C18—H18B	108.00
C19—O2—C7—O4	−88.4 (4)	O4—C7—C12—C11	−70.2 (5)
C19—O2—C7—C8	158.3 (4)	O4—C7—C12—C13	58.0 (4)
C19—O2—C7—C12	32.9 (5)	C8—C7—C12—C11	49.2 (5)
C7—O2—C19—C14	−2.0 (7)	C8—C7—C12—C13	177.4 (4)
C7—O2—C19—C18	178.7 (4)	C7—C8—C9—C10	55.9 (5)
C7—O4—C6—C1	176.9 (4)	C8—C9—C10—C11	−53.0 (6)
C7—O4—C6—C5	−3.2 (6)	C9—C10—C11—O1	−134.8 (5)
C6—O4—C7—O2	96.0 (4)	C9—C10—C11—C12	48.4 (6)
C6—O4—C7—C8	−149.7 (4)	O1—C11—C12—C7	136.7 (5)
C6—O4—C7—C12	−25.8 (5)	O1—C11—C12—C13	13.0 (6)
Br1—C1—C2—C3	−178.8 (4)	C10—C11—C12—C7	−46.4 (5)
C6—C1—C2—C3	1.6 (7)	C10—C11—C12—C13	−170.0 (4)
Br1—C1—C6—O4	0.9 (6)	C7—C12—C13—C5	−62.3 (5)
Br1—C1—C6—C5	−179.1 (3)	C7—C12—C13—C14	57.0 (4)
C2—C1—C6—O4	−179.5 (4)	C11—C12—C13—C5	63.8 (5)
C2—C1—C6—C5	0.5 (7)	C11—C12—C13—C14	−176.9 (4)
C1—C2—C3—Cl1	175.9 (4)	C5—C13—C14—C15	−90.3 (5)
C1—C2—C3—C4	−2.0 (7)	C5—C13—C14—C19	88.6 (6)
Cl1—C3—C4—C5	−177.6 (4)	C12—C13—C14—C15	151.7 (4)
C2—C3—C4—C5	0.3 (8)	C12—C13—C14—C19	−29.4 (6)
C3—C4—C5—C6	1.9 (7)	C13—C14—C15—O3	7.1 (7)
C3—C4—C5—C13	−178.0 (4)	C13—C14—C15—C16	−172.2 (4)
C4—C5—C6—O4	177.7 (4)	C19—C14—C15—O3	−171.9 (5)
C4—C5—C6—C1	−2.3 (7)	C19—C14—C15—C16	8.8 (7)
C13—C5—C6—O4	−2.4 (7)	C13—C14—C19—O2	0.7 (7)
C13—C5—C6—C1	177.6 (4)	C13—C14—C19—C18	180.0 (4)
C4—C5—C13—C12	−144.7 (5)	C15—C14—C19—O2	179.7 (4)
C4—C5—C13—C14	97.8 (5)	C15—C14—C19—C18	−1.1 (8)
C6—C5—C13—C12	35.4 (6)	O3—C15—C16—C17	144.8 (5)
C6—C5—C13—C14	−82.2 (5)	C14—C15—C16—C17	−35.9 (6)
O2—C7—C8—C9	−178.8 (4)	C15—C16—C17—C18	54.9 (6)
O4—C7—C8—C9	67.5 (5)	C16—C17—C18—C19	−46.2 (6)
C12—C7—C8—C9	−54.7 (5)	C17—C18—C19—O2	−160.1 (4)
O2—C7—C12—C11	171.0 (4)	C17—C18—C19—C14	20.5 (7)
O2—C7—C12—C13	−60.8 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O3i	0.99	2.53	3.407 (6)	147
C9—H9B···Cg3ii	0.99	2.89	3.731 (5)	143

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O3i	0.99	2.53	3.407 (6)	147
C9—H9B⋯Cg3ii	0.99	2.89	3.731 (5)	143

Symmetry codes: (i) ; (ii) .