2,4-Di-bromo-1,3-dihy-droxy-9H-xanthen-9-one.

The title compound, C13H6Br2O4, derived from xanthone, a fundamental structural framework of active ingredients in many medicinal plants, and was synthesized by bromination of 1,3-di-hydroxyxanthen-9-one with N-bromo-succinimide. The mol-ecular conformation is essentially planar, the dihedral angle between the benzene rings being 1.1 (4)°. This conformation is favorable for the formation of an intra-molecular O-H⋯O hydrogen bond between a hy-droxy group and the xanthone carbonyl group. In the crystal, mol-ecules are associated into chains along the b-axis direction via C=O⋯H-O hydrogen bonds involving the other hy-droxy group.

Related literature

For the pharmacological activity of xanthone derivatives, see: Cheng et al. (2011 ▶); Dao et al. (2012 ▶); Sousa et al. (2009 ▶); Szkaradek et al. (2013 ▶). For the synthesis of the xanthone used as a starting material, see: Liu et al. (2006 ▶). For related xanthone structures, see: Corrêa et al. (2010 ▶).

Experimental

Crystal data

C13H6Br2O4

M = 386.00

Orthorhombic,

a = 18.4489 (15) Å

b = 16.9049 (13) Å

c = 3.8564 (3) Å

V = 1202.72 (16) Å3

Z = 4

Mo Kα radiation

μ = 6.75 mm−1

T = 298 K

0.28 × 0.09 × 0.06 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.254, T max = 0.688

6188 measured reflections

2120 independent reflections

1830 reflections with I > 2σ(I)

R int = 0.076

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.070

S = 1.04

2120 reflections

172 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.33 e Å−3

Absolute structure: Flack (1983 ▶), 881 Friedel pairs

Absolute structure parameter: −0.008 (16)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT (Bruker, 1998 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXL97 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813019296/bh2480sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813019296/bh2480Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019296/bh2480Isup3.cdx

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813019296/bh2480Isup4.cml

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

C13H6Br2O4	F(000) = 744
Mr = 386.00	Dx = 2.132 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2778 reflections
a = 18.4489 (15) Å	θ = 3.3–26.2°
b = 16.9049 (13) Å	µ = 6.75 mm−1
c = 3.8564 (3) Å	T = 298 K
V = 1202.72 (16) Å3	Block, yellow
Z = 4	0.28 × 0.09 × 0.06 mm

Bruker SMART CCD diffractometer	2120 independent reflections
Radiation source: fine-focus sealed tube	1830 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −21→21
Tmin = 0.254, Tmax = 0.688	k = −20→15
6188 measured reflections	l = −4→4

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0232P)2] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.002
2120 reflections	Δρmax = 0.43 e Å−3
172 parameters	Δρmin = −0.33 e Å−3
1 restraint	Absolute structure: Flack (1983), 881 Friedel pairs
0 constraints	Flack parameter: −0.008 (16)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Br1	0.65912 (3)	1.09241 (3)	−0.07056 (16)	0.03711 (16)
Br2	0.91885 (3)	0.97740 (3)	0.54899 (17)	0.03972 (17)
O1	0.61335 (17)	0.9267 (2)	0.0466 (12)	0.0366 (9)
O2	0.72160 (18)	0.7368 (2)	0.4658 (13)	0.0483 (11)
O3	0.8177 (2)	1.0920 (2)	0.2248 (11)	0.0408 (11)
H3	0.7904	1.1248	0.1377	0.061*
O4	0.83232 (18)	0.8253 (2)	0.5513 (13)	0.0452 (11)
H4	0.8074	0.7851	0.5521	0.068*
C1	0.6824 (3)	0.9348 (3)	0.1582 (13)	0.0262 (13)
C2	0.7137 (3)	1.0086 (3)	0.1241 (13)	0.0277 (13)
C3	0.7844 (3)	1.0223 (3)	0.2401 (14)	0.0293 (13)
C4	0.8233 (3)	0.9589 (3)	0.3828 (15)	0.0310 (14)
C5	0.7941 (3)	0.8853 (3)	0.4141 (16)	0.0323 (13)
C6	0.7210 (3)	0.8704 (3)	0.2998 (14)	0.0305 (14)
C7	0.6879 (3)	0.7943 (4)	0.3340 (15)	0.0351 (15)
C8	0.6131 (3)	0.7875 (3)	0.2015 (14)	0.0337 (14)
C9	0.5753 (3)	0.7164 (4)	0.2048 (17)	0.0400 (15)
H9	0.5977	0.6707	0.2858	0.048*
C10	0.5053 (3)	0.7135 (4)	0.0887 (19)	0.0479 (16)
H10	0.4797	0.6661	0.0978	0.057*
C11	0.4724 (3)	0.7802 (4)	−0.0412 (18)	0.0458 (15)
H11	0.4251	0.7770	−0.1236	0.055*
C12	0.5080 (3)	0.8511 (3)	−0.0515 (17)	0.0410 (14)
H12	0.4853	0.8965	−0.1333	0.049*
C13	0.5793 (3)	0.8533 (3)	0.0642 (17)	0.0314 (12)

	U11	U22	U33	U12	U13	U23
Br1	0.0367 (3)	0.0309 (3)	0.0438 (3)	0.0061 (2)	−0.0024 (3)	0.0080 (3)
Br2	0.0277 (3)	0.0461 (4)	0.0454 (3)	−0.0007 (2)	−0.0040 (3)	0.0016 (3)
O1	0.0249 (19)	0.033 (2)	0.052 (2)	0.0044 (15)	−0.007 (2)	0.008 (2)
O2	0.037 (2)	0.027 (2)	0.081 (3)	0.0009 (17)	−0.006 (3)	0.015 (2)
O3	0.040 (2)	0.025 (2)	0.058 (3)	−0.0020 (19)	−0.005 (2)	0.012 (2)
O4	0.032 (2)	0.037 (2)	0.067 (3)	0.0062 (16)	−0.010 (3)	0.015 (2)
C1	0.025 (3)	0.026 (3)	0.027 (3)	0.006 (2)	0.000 (2)	−0.002 (2)
C2	0.028 (3)	0.028 (3)	0.026 (4)	0.012 (2)	−0.002 (2)	0.001 (2)
C3	0.028 (3)	0.028 (3)	0.032 (3)	0.003 (3)	0.005 (2)	0.003 (3)
C4	0.022 (3)	0.036 (3)	0.034 (3)	0.000 (2)	0.006 (3)	−0.002 (3)
C5	0.027 (3)	0.036 (3)	0.034 (3)	0.006 (2)	0.005 (3)	0.008 (3)
C6	0.033 (3)	0.023 (3)	0.036 (3)	0.008 (2)	0.003 (2)	0.005 (2)
C7	0.028 (3)	0.037 (4)	0.041 (4)	0.001 (3)	0.008 (3)	0.003 (3)
C8	0.037 (4)	0.034 (4)	0.031 (3)	0.002 (3)	−0.001 (3)	−0.003 (3)
C9	0.038 (4)	0.028 (3)	0.054 (4)	−0.004 (3)	0.002 (3)	0.001 (3)
C10	0.040 (4)	0.048 (4)	0.056 (4)	−0.008 (3)	−0.003 (3)	0.003 (3)
C11	0.030 (3)	0.056 (4)	0.051 (4)	−0.007 (3)	−0.004 (3)	0.001 (4)
C12	0.028 (3)	0.048 (4)	0.048 (4)	0.006 (3)	−0.008 (3)	−0.001 (3)
C13	0.034 (3)	0.032 (3)	0.029 (3)	−0.001 (2)	0.010 (3)	0.001 (3)

Br1—C2	1.893 (5)	C5—C6	1.442 (7)
Br2—C4	1.902 (5)	C6—C7	1.429 (8)
O1—C1	1.351 (6)	C7—C8	1.476 (8)
O1—C13	1.393 (6)	C8—C13	1.379 (7)
O2—C7	1.262 (7)	C8—C9	1.390 (8)
O3—C3	1.331 (7)	C9—C10	1.368 (8)
O3—H3	0.8200	C9—H9	0.9300
O4—C5	1.343 (6)	C10—C11	1.374 (8)
O4—H4	0.8200	C10—H10	0.9300
C1—C2	1.381 (7)	C11—C12	1.368 (8)
C1—C6	1.411 (7)	C11—H11	0.9300
C2—C3	1.398 (7)	C12—C13	1.389 (7)
C3—C4	1.402 (7)	C12—H12	0.9300
C4—C5	1.361 (7)
C1—O1—C13	119.9 (4)	O2—C7—C6	121.3 (5)
C3—O3—H3	109.5	O2—C7—C8	122.7 (5)
C5—O4—H4	109.5	C6—C7—C8	115.9 (5)
O1—C1—C2	117.1 (4)	C13—C8—C9	118.4 (5)
O1—C1—C6	121.4 (5)	C13—C8—C7	119.5 (5)
C2—C1—C6	121.5 (5)	C9—C8—C7	122.2 (5)
C1—C2—C3	120.6 (5)	C10—C9—C8	120.0 (6)
C1—C2—Br1	119.4 (4)	C10—C9—H9	120.0
C3—C2—Br1	120.0 (4)	C8—C9—H9	120.0
O3—C3—C2	124.2 (5)	C9—C10—C11	120.5 (6)
O3—C3—C4	117.3 (5)	C9—C10—H10	119.8
C2—C3—C4	118.5 (5)	C11—C10—H10	119.8
C5—C4—C3	122.1 (5)	C12—C11—C10	121.2 (5)
C5—C4—Br2	119.1 (4)	C12—C11—H11	119.4
C3—C4—Br2	118.8 (4)	C10—C11—H11	119.4
O4—C5—C4	121.2 (5)	C11—C12—C13	117.9 (5)
O4—C5—C6	118.6 (5)	C11—C12—H12	121.1
C4—C5—C6	120.2 (5)	C13—C12—H12	121.1
C1—C6—C7	121.0 (5)	C8—C13—C12	122.0 (5)
C1—C6—C5	117.1 (5)	C8—C13—O1	122.3 (5)
C7—C6—C5	121.9 (5)	C12—C13—O1	115.7 (5)
C13—O1—C1—C2	178.1 (5)	O4—C5—C6—C7	1.1 (9)
C13—O1—C1—C6	−1.2 (8)	C4—C5—C6—C7	−178.8 (5)
O1—C1—C2—C3	178.6 (5)	C1—C6—C7—O2	−178.7 (5)
C6—C1—C2—C3	−2.1 (8)	C5—C6—C7—O2	−0.1 (9)
O1—C1—C2—Br1	0.3 (6)	C1—C6—C7—C8	2.1 (8)
C6—C1—C2—Br1	179.6 (4)	C5—C6—C7—C8	−179.2 (5)
C1—C2—C3—O3	−178.2 (5)	O2—C7—C8—C13	179.3 (6)
Br1—C2—C3—O3	0.1 (8)	C6—C7—C8—C13	−1.6 (8)
C1—C2—C3—C4	1.7 (8)	O2—C7—C8—C9	−1.8 (9)
Br1—C2—C3—C4	−180.0 (4)	C6—C7—C8—C9	177.3 (5)
O3—C3—C4—C5	179.3 (5)	C13—C8—C9—C10	−3.0 (9)
C2—C3—C4—C5	−0.6 (9)	C7—C8—C9—C10	178.0 (6)
O3—C3—C4—Br2	1.0 (7)	C8—C9—C10—C11	1.9 (11)
C2—C3—C4—Br2	−178.9 (4)	C9—C10—C11—C12	−1.3 (12)
C3—C4—C5—O4	179.9 (6)	C10—C11—C12—C13	1.9 (10)
Br2—C4—C5—O4	−1.8 (8)	C9—C8—C13—C12	3.7 (9)
C3—C4—C5—C6	−0.2 (9)	C7—C8—C13—C12	−177.4 (6)
Br2—C4—C5—C6	178.1 (4)	C9—C8—C13—O1	−179.2 (6)
O1—C1—C6—C7	−0.8 (8)	C7—C8—C13—O1	−0.3 (9)
C2—C1—C6—C7	179.9 (5)	C11—C12—C13—C8	−3.1 (10)
O1—C1—C6—C5	−179.5 (5)	C11—C12—C13—O1	179.6 (6)
C2—C1—C6—C5	1.2 (8)	C1—O1—C13—C8	1.7 (9)
O4—C5—C6—C1	179.8 (5)	C1—O1—C13—C12	179.0 (5)
C4—C5—C6—C1	−0.1 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···Br1	0.82	2.61	3.139 (5)	124
O4—H4···O2	0.82	1.81	2.555 (7)	149
O3—H3···O2i	0.82	2.02	2.741 (7)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2	0.82	1.81	2.555 (7)	149
O3—H3⋯O2i	0.82	2.02	2.741 (7)	147

Symmetry code: (i) .