6,8-Dibromo-5-hydr­oxy-4-oxo-2-phenyl-4H-chromen-7-yl acetate

Nallasivam, A.; Nethaji, M.; Vembu, N.; Ragunathan, V.; Sulochana, N.

doi:10.1107/S1600536809005431

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o568

doi:10.1107/S1600536809005431

Open

access

6,8-Dibromo-5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl acetate

Angannan Nallasivam,^a Munirathinam Nethaji,^b Nagarajan Vembu,^c ^* Venkatraman Ragunathan ^d and Nagarajan Sulochana ^a

^aDepartment of Chemistry, National Institute of Technology, Tiruchirappalli 620 015, India, ^bDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India, ^cDepartment of Chemistry, Urumu Dhanalakshmi College, Tiruchirappalli 620 019, India, and ^dDepartment of Chemistry, Kandasamy Kandar College, Velur 638 182, India
^*Correspondence e-mail: vembu57@yahoo.com

(Received 12 January 2009; accepted 16 February 2009; online 21 February 2009)

In the title compound, C₁₇H₁₀Br₂O₅, the chromene ring is almost planar with minimal puckering [total puckering amplitude = 0.067 (4) Å]. The dihedral angle between chromeme ring system and phenyl ring is 3.7 (2)°. The crystal structure is stabilized by intermolecular C—H⋯O interactions and an intramolecular O—H⋯O hydrogen bond also occurs.

Related literature

For the biological and pharmacological properties of benzopyrans and their derivatives, see: Brooks (1998 ); Hatakeyama et al. (1988 )); Hyana & Saimoto (1987 ); Tang et al. (2007 ). For the importance of 4H-chromenes, see: Liu et al. (2007 ); Wang, Fang et al. (2003 ); Wang, Zhang et al. (2003 ). For hydrogen bonding, see: Bernstein et al. (1995 ); Desiraju (1989 ); Desiraju & Steiner (1999 ); Etter (1990 ).

Experimental

Crystal data

C₁₇H₁₀Br₂O₅
M_r = 454.07
Monoclinic, P 2₁ /n
a = 14.072 (3) Å
b = 5.5586 (13) Å
c = 21.333 (5) Å
β = 104.501 (4)°
V = 1615.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 5.04 mm⁻¹
T = 293 K
0.55 × 0.23 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.157, T_max = 0.547
13326 measured reflections
3773 independent reflections
2245 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.105
S = 0.99
3773 reflections
221 parameters
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H12⋯O11	0.82	1.86	2.584 (4)	147
C3—H3⋯O11ⁱ	0.93	2.57	3.497 (4)	171
C24—H24⋯O11ⁱ	0.93	2.48	3.387 (5)	166
C17—H17A⋯O16ⁱⁱ	0.96	2.58	3.309 (6)	133
Symmetry codes: (i) -x+1, -y-1, -z; (ii) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809005431/er2060sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809005431/er2060Isup2.hkl

checkCIF report

Comment top

Chromenes (benzopyrans) and their derivatives have numerous biological and pharmacological properties (Tang et al., 2007) such as antisterility (Brooks, 1998) and anticancer activity (Hyana & Saimoto, 1987). In addition, polyfunctionalized chromene units are present in numerous natural products (Hatakeyama et al., 1988). 4H-chromenes are important synthons for some natural products (Liu et al., 2007). As a part of our structural investigations on 4H-chromene derivatives and compounds containing the benzopyran fragment, the single-crystal X-ray diffraction study on the title compound was carried out.

The chromene ring is almost planar similarly as those found in the related chromene derivatives (Wang, Fang et al., 2003; Wang, Zhang et al., 2003). The total puckering amplitude of the chromene ring is 0.067 (4) Å in the title structure. The interplanar angle between the chromene ring and the 2-phenyl ring is 3.7 (2)° thereby indicating the almost coplanar arrangement (Fig. 1). The OCOCH₃ substituent at C7 is non-coplanar with the chromene ring as discerned from the interplanar angle of 87.4 (1)°.

The crystal structure is stabilized by the interplay of C–H···O and O–H···O interactions (Fig. 2 & Table 1). The H-bond distances agree with those reported in literature (Desiraju & Steiner, 1999; Desiraju, 1989). The C20–H20···O1 interaction generates a motif of graph set (Bernstein et al., 1995; Etter, 1990) S(5). An S(6) motif is formed by O12–H12···O11 interaction. This interaction is also responsible for the formation of a cooperative H-bonded network (Fig. 3). The C3–H3···O11ⁱ and C24–H24···O11ⁱ interactions constitute a pair of bifurcated acceptor bonds generating a ring of graph set R¹₂(7). There are no significant C—H···π and π···π interactions.

Related literature top

For the biological and pharmacological properties of benzopyrans and their derivatives, see: Brooks (1998); Hatakeyama et al. (1988)); Hyana & Saimoto (1987); Tang et al. (2007). For the importance of 4H-chromenes, see: Liu et al. (2007); Wang, Fang et al. (2003); Wang, Zhang et al. (2003). For hydrogen bonding, see: Bernstein et al. (1995); Desiraju (1989); Desiraju & Steiner (1999); Etter (1990).

Experimental top

In to the RBF, a suspension of chrysin (1 g, 3.93 mmol) and potassium carbonate (1.64 g, 11.81 mmol) in dimethyl formamide (10 ml) were added. The reaction mixture was heated to 383 K for 2–3 hrs. The reaction mixture was cooled to 313 K and acetyl chloride (1.23 g, 15.74 mmol) was slowly added with the help of dropping funnel. The reaction mixture was maintained for 8–9 hr at 313 K and monitored by HPLC. After completion of the reaction, the contents were quenched with water and stirred for 30–45 min at 303 K. The crude solid obtained was filtered and washed with plenty of water followed by methanol and dried under vacuum at 343 K. The acetylated compound was then taken in RBF and dissolved in dichloromethane (10 ml) and cooled to 273 K. Bromine (0.6 ml, 11.81 mmol) was added dropwise over a period of 15–20 min. The reaction mixture was maintained at 273 K for 5–6 hr. After completion of the reaction, the reaction mixture was quenched in ice water and extracted with dichloromethane (10 ml) and purified by column chromatography using ethyl acetate: n-hexane (20:80). The crude brominated product was then dissolved in dichloromethane (10 ml) and equal amount of n-Hexane (10 ml). The clear solution was kept for a week without stirring. Diffraction quality needle shaped crystals of average size 0.23 mm were obtained which were filtered and washed with n-hexane and dried under vacuum at 343 K. Yield: 80%

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit with the atoms labelled and displacement ellipsoids depicted at the 50% probability level for all non-H atoms. H-atoms are drawn as spheres of arbitrary radius.
	Fig. 2. The molecular packing viewed down the b-axis. Dashed lines represent the weak C–H···O interactions within the lattice.
	Fig. 3. Cooperative H-bonded network of O–H···O interactions viewed down the a-axis

6,8-Dibromo-5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl acetate top

Crystal data top

C₁₇H₁₀Br₂O₅	F(000) = 888
M_r = 454.07	D_x = 1.867 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 433–435 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 14.072 (3) Å	Cell parameters from 475 reflections
b = 5.5586 (13) Å	θ = 2.0–27.0°
c = 21.333 (5) Å	µ = 5.04 mm⁻¹
β = 104.501 (4)°	T = 293 K
V = 1615.6 (7) Å³	Rectangular, brown
Z = 4	0.55 × 0.23 × 0.12 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3773 independent reflections
Radiation source: fine-focus sealed tube	2245 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
Detector resolution: 8.3 pixels mm^-1	θ_max = 28.0°, θ_min = 2.0°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	k = −7→7
T_min = 0.157, T_max = 0.547	l = −25→28
13326 measured reflections

Refinement top

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0505P)²] where P = (F_o² + 2F_c²)/3
3773 reflections	(Δ/σ)_max = 0.001
221 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₇H₁₀Br₂O₅	V = 1615.6 (7) Å³
M_r = 454.07	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.072 (3) Å	µ = 5.04 mm⁻¹
b = 5.5586 (13) Å	T = 293 K
c = 21.333 (5) Å	0.55 × 0.23 × 0.12 mm
β = 104.501 (4)°

Data collection top

Bruker SMART APEX CCD diffractometer	3773 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	2245 reflections with I > 2σ(I)
T_min = 0.157, T_max = 0.547	R_int = 0.046
13326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 0.99	Δρ_max = 0.57 e Å⁻³
3773 reflections	Δρ_min = −0.37 e Å⁻³
221 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.75605 (17)	−0.0593 (5)	−0.00552 (13)	0.0490 (7)
C2	0.6921 (3)	−0.2392 (7)	−0.03148 (18)	0.0441 (9)
C3	0.6143 (3)	−0.2872 (7)	−0.00800 (19)	0.0444 (9)
H3	0.5734	−0.4146	−0.0256	0.069 (6)*
C4	0.5916 (3)	−0.1506 (7)	0.04288 (19)	0.0429 (9)
C5	0.6440 (3)	0.1983 (7)	0.11713 (18)	0.0424 (9)
C6	0.7094 (3)	0.3853 (7)	0.13882 (18)	0.0455 (9)
C7	0.7897 (3)	0.4160 (7)	0.11257 (19)	0.0484 (10)
C8	0.8070 (3)	0.2636 (7)	0.0658 (2)	0.0474 (10)
C9	0.7396 (3)	0.0821 (7)	0.04300 (18)	0.0416 (9)
C10	0.6588 (3)	0.0450 (6)	0.06832 (18)	0.0419 (9)
O11	0.51819 (18)	−0.1904 (5)	0.06422 (13)	0.0506 (7)
O12	0.5671 (2)	0.1687 (5)	0.14257 (14)	0.0550 (7)
H12	0.5375	0.0458	0.1279	0.101 (9)*
Br13	0.68667 (3)	0.60136 (8)	0.20112 (2)	0.06240 (17)
O14	0.8497 (2)	0.6151 (5)	0.13072 (15)	0.0600 (8)
C15	0.9279 (3)	0.5925 (8)	0.1845 (2)	0.0523 (10)
O16	0.9461 (2)	0.4080 (6)	0.21218 (15)	0.0660 (8)
C17	0.9808 (3)	0.8239 (8)	0.1978 (3)	0.0747 (15)
H17A	0.9374	0.9448	0.2069	0.101 (9)*
H17B	1.0033	0.8711	0.1607	0.101 (9)*
H17C	1.0361	0.8062	0.2345	0.101 (9)*
Br18	0.91815 (3)	0.30002 (10)	0.03298 (2)	0.06851 (18)
C19	0.7192 (3)	−0.3583 (7)	−0.08556 (19)	0.0471 (10)
C20	0.8013 (3)	−0.2850 (9)	−0.1052 (2)	0.0607 (12)
H20	0.8397	−0.1587	−0.0841	0.069 (6)*
C21	0.8258 (3)	−0.4012 (10)	−0.1563 (2)	0.0741 (14)
H21	0.8810	−0.3525	−0.1694	0.069 (6)*
C22	0.7703 (4)	−0.5856 (10)	−0.1876 (2)	0.0751 (14)
H22	0.7879	−0.6629	−0.2217	0.069 (6)*
C23	0.6888 (4)	−0.6571 (9)	−0.1692 (2)	0.0781 (15)
H23	0.6507	−0.7828	−0.1908	0.069 (6)*
C24	0.6626 (3)	−0.5442 (8)	−0.1186 (2)	0.0650 (12)
H24	0.6065	−0.5930	−0.1065	0.069 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0447 (14)	0.0548 (18)	0.0464 (16)	−0.0054 (12)	0.0096 (12)	−0.0050 (14)
C2	0.044 (2)	0.046 (2)	0.039 (2)	0.0008 (17)	0.0044 (18)	−0.0001 (19)
C3	0.044 (2)	0.042 (2)	0.043 (2)	−0.0052 (18)	0.0043 (18)	−0.0035 (19)
C4	0.042 (2)	0.046 (3)	0.038 (2)	0.0027 (17)	0.0031 (17)	0.0030 (18)
C5	0.045 (2)	0.043 (2)	0.037 (2)	0.0052 (18)	0.0067 (18)	0.0068 (19)
C6	0.058 (2)	0.034 (2)	0.038 (2)	0.0010 (18)	0.0007 (18)	0.0031 (18)
C7	0.057 (2)	0.035 (2)	0.045 (2)	−0.0042 (19)	−0.003 (2)	0.005 (2)
C8	0.043 (2)	0.046 (3)	0.049 (3)	−0.0046 (18)	0.0034 (18)	0.009 (2)
C9	0.044 (2)	0.041 (2)	0.036 (2)	0.0044 (17)	0.0052 (17)	0.0021 (19)
C10	0.044 (2)	0.039 (2)	0.039 (2)	0.0016 (17)	0.0027 (17)	−0.0013 (17)
O11	0.0463 (14)	0.0556 (17)	0.0504 (17)	−0.0071 (13)	0.0128 (13)	−0.0059 (14)
O12	0.0583 (17)	0.054 (2)	0.0540 (19)	−0.0002 (14)	0.0171 (15)	−0.0058 (14)
Br13	0.0923 (4)	0.0435 (3)	0.0465 (3)	0.0055 (2)	0.0083 (2)	−0.0046 (2)
O14	0.0682 (18)	0.0392 (16)	0.064 (2)	−0.0116 (14)	0.0006 (16)	0.0060 (15)
C15	0.054 (2)	0.040 (2)	0.062 (3)	−0.005 (2)	0.011 (2)	−0.013 (2)
O16	0.071 (2)	0.0481 (19)	0.067 (2)	−0.0012 (16)	−0.0046 (16)	0.0045 (17)
C17	0.067 (3)	0.052 (3)	0.101 (4)	−0.014 (2)	0.015 (3)	−0.014 (3)
Br18	0.0579 (3)	0.0773 (4)	0.0723 (4)	−0.0162 (2)	0.0200 (2)	0.0048 (3)
C19	0.048 (2)	0.052 (3)	0.038 (2)	0.0083 (19)	0.0036 (18)	0.0017 (19)
C20	0.056 (2)	0.075 (3)	0.050 (3)	−0.003 (2)	0.012 (2)	−0.003 (2)
C21	0.064 (3)	0.105 (4)	0.058 (3)	0.003 (3)	0.025 (2)	−0.011 (3)
C22	0.083 (3)	0.094 (4)	0.051 (3)	0.011 (3)	0.024 (3)	−0.020 (3)
C23	0.091 (4)	0.081 (4)	0.065 (3)	−0.015 (3)	0.026 (3)	−0.033 (3)
C24	0.070 (3)	0.066 (3)	0.063 (3)	−0.006 (2)	0.024 (2)	−0.012 (3)

Geometric parameters (Å, º) top

O1—C9	1.365 (4)	O12—H12	0.8200
O1—C2	1.366 (4)	O14—C15	1.383 (5)
C2—C3	1.340 (5)	C15—O16	1.179 (5)
C2—C19	1.461 (5)	C15—C17	1.478 (6)
C3—C4	1.425 (5)	C17—H17A	0.9600
C3—H3	0.9300	C17—H17B	0.9600
C4—O11	1.249 (4)	C17—H17C	0.9600
C4—C10	1.454 (5)	C19—C20	1.385 (5)
C5—O12	1.337 (4)	C19—C24	1.385 (6)
C5—C6	1.388 (5)	C20—C21	1.383 (6)
C5—C10	1.401 (5)	C20—H20	0.9300
C6—C7	1.392 (6)	C21—C22	1.359 (7)
C6—Br13	1.877 (4)	C21—H21	0.9300
C7—C8	1.376 (6)	C22—C23	1.362 (7)
C7—O14	1.387 (4)	C22—H22	0.9300
C8—C9	1.387 (5)	C23—C24	1.376 (6)
C8—Br18	1.878 (4)	C23—H23	0.9300
C9—C10	1.391 (5)	C24—H24	0.9300

C9—O1—C2	120.6 (3)	C15—O14—C7	117.5 (3)
C3—C2—O1	120.7 (3)	O16—C15—O14	121.5 (4)
C3—C2—C19	127.2 (4)	O16—C15—C17	128.7 (4)
O1—C2—C19	112.1 (3)	O14—C15—C17	109.8 (4)
C2—C3—C4	122.6 (4)	C15—C17—H17A	109.5
C2—C3—H3	118.7	C15—C17—H17B	109.5
C4—C3—H3	118.7	H17A—C17—H17B	109.5
O11—C4—C3	123.1 (3)	C15—C17—H17C	109.5
O11—C4—C10	121.1 (3)	H17A—C17—H17C	109.5
C3—C4—C10	115.8 (3)	H17B—C17—H17C	109.5
O12—C5—C6	119.5 (4)	C20—C19—C24	118.9 (4)
O12—C5—C10	120.8 (3)	C20—C19—C2	120.5 (4)
C6—C5—C10	119.6 (3)	C24—C19—C2	120.6 (4)
C5—C6—C7	119.6 (4)	C21—C20—C19	119.5 (4)
C5—C6—Br13	120.0 (3)	C21—C20—H20	120.3
C7—C6—Br13	120.4 (3)	C19—C20—H20	120.3
C8—C7—O14	119.2 (4)	C22—C21—C20	121.0 (5)
C8—C7—C6	121.7 (4)	C22—C21—H21	119.5
O14—C7—C6	119.0 (4)	C20—C21—H21	119.5
C7—C8—C9	118.2 (4)	C21—C22—C23	120.0 (5)
C7—C8—Br18	121.3 (3)	C21—C22—H22	120.0
C9—C8—Br18	120.5 (3)	C23—C22—H22	120.0
O1—C9—C8	117.0 (3)	C22—C23—C24	120.3 (5)
O1—C9—C10	121.3 (3)	C22—C23—H23	119.9
C8—C9—C10	121.7 (4)	C24—C23—H23	119.9
C9—C10—C5	119.1 (3)	C23—C24—C19	120.4 (4)
C9—C10—C4	119.0 (3)	C23—C24—H24	119.8
C5—C10—C4	121.9 (3)	C19—C24—H24	119.8
C5—O12—H12	109.5

C9—O1—C2—C3	−2.9 (5)	O1—C9—C10—C4	0.8 (5)
C9—O1—C2—C19	176.1 (3)	C8—C9—C10—C4	−179.1 (3)
O1—C2—C3—C4	2.4 (6)	O12—C5—C10—C9	179.8 (3)
C19—C2—C3—C4	−176.5 (4)	C6—C5—C10—C9	0.7 (5)
C2—C3—C4—O11	178.4 (4)	O12—C5—C10—C4	0.4 (5)
C2—C3—C4—C10	−0.3 (5)	C6—C5—C10—C4	−178.7 (3)
O12—C5—C6—C7	179.8 (3)	O11—C4—C10—C9	180.0 (3)
C10—C5—C6—C7	−1.1 (5)	C3—C4—C10—C9	−1.3 (5)
O12—C5—C6—Br13	−2.3 (5)	O11—C4—C10—C5	−0.6 (6)
C10—C5—C6—Br13	176.8 (3)	C3—C4—C10—C5	178.2 (3)
C5—C6—C7—C8	−0.7 (6)	C8—C7—O14—C15	−95.3 (4)
Br13—C6—C7—C8	−178.6 (3)	C6—C7—O14—C15	89.3 (4)
C5—C6—C7—O14	174.6 (3)	C7—O14—C15—O16	3.5 (6)
Br13—C6—C7—O14	−3.2 (5)	C7—O14—C15—C17	−177.8 (4)
O14—C7—C8—C9	−172.6 (3)	C3—C2—C19—C20	178.7 (4)
C6—C7—C8—C9	2.7 (6)	O1—C2—C19—C20	−0.3 (5)
O14—C7—C8—Br18	7.0 (5)	C3—C2—C19—C24	−0.4 (6)
C6—C7—C8—Br18	−177.7 (3)	O1—C2—C19—C24	−179.4 (4)
C2—O1—C9—C8	−178.8 (3)	C24—C19—C20—C21	−1.1 (6)
C2—O1—C9—C10	1.3 (5)	C2—C19—C20—C21	179.7 (4)
C7—C8—C9—O1	177.0 (3)	C19—C20—C21—C22	0.2 (7)
Br18—C8—C9—O1	−2.6 (5)	C20—C21—C22—C23	0.5 (8)
C7—C8—C9—C10	−3.1 (6)	C21—C22—C23—C24	−0.3 (8)
Br18—C8—C9—C10	177.4 (3)	C22—C23—C24—C19	−0.6 (8)
O1—C9—C10—C5	−178.7 (3)	C20—C19—C24—C23	1.4 (7)
C8—C9—C10—C5	1.4 (5)	C2—C19—C24—C23	−179.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O11	0.82	1.86	2.584 (4)	147
C20—H20···O1	0.93	2.34	2.679 (5)	101
C3—H3···O11ⁱ	0.93	2.57	3.497 (4)	171
C24—H24···O11ⁱ	0.93	2.48	3.387 (5)	166
C17—H17A···O16ⁱⁱ	0.96	2.58	3.309 (6)	133

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀Br₂O₅
M_r	454.07
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	14.072 (3), 5.5586 (13), 21.333 (5)
β (°)	104.501 (4)
V (Å³)	1615.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.04
Crystal size (mm)	0.55 × 0.23 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.157, 0.547
No. of measured, independent and observed [I > 2σ(I)] reflections	13326, 3773, 2245
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.659

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.105, 0.99
No. of reflections	3773
No. of parameters	221
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.37

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O12—H12···O11	0.82	1.86	2.584 (4)	146.5
C20—H20···O1	0.93	2.34	2.679 (5)	100.8
C3—H3···O11ⁱ	0.93	2.57	3.497 (4)	171.1
C24—H24···O11ⁱ	0.93	2.48	3.387 (5)	166.0
C17—H17A···O16ⁱⁱ	0.96	2.58	3.309 (6)	133.0

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

Acknowledgements

AN thanks Dr S. Kannan and Dr B. S. Krishnamurthy, School of Chemistry, Bharathidasan University, Tiruchirappalli, and Organica Aromatics Pvt Ltd Bangalore, India, for providing laboratory facilities.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brooks, G. T. (1998). Pestic. Sci. 22, 41–50. CrossRef Web of Science Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. (1989). Crystal Engineering: The Design of Organic Solids, pp. 125–167. Amsterdam: Elsevier. Google Scholar
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, pp. 11–40. New York: Oxford University Press. Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Hatakeyama, S., Ochi, N., Numata, H. & Takano, S. (1988). J. Chem. Soc. Chem. Commun. pp. 1022–1024. Google Scholar
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768. Google Scholar
Liu, C.-B., Chen, Y.-H., Zhou, X.-Y., Ding, L. & Wen, H.-L. (2007). Acta Cryst. E63, o90–o91. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437–o1438. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Wang, J.-F., Fang, M.-J., Huang, H.-Q., Li, G.-L., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1517–o1518. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, J.-F., Zhang, Y.-J., Fang, M.-J., Huang, Y.-J., Wei, Z.-B., Zheng, Z.-H., Su, W.-J. & Zhao, Y.-F. (2003). Acta Cryst. E59, o1244–o1245. Web of Science CSD CrossRef IUCr Journals Google Scholar