(Z)-Methyl 2-[(4-bromo-2-formyl­phen­oxy)meth­yl]-3-o-tolyl­acrylate

Vijayakumar, S.; Madhanraj, R.; Murugavel, S.; Selvakumar, R.; Bakthadoss, M.

doi:10.1107/S1600536811037731

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2690

https://doi.org/10.1107/S1600536811037731

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(Z)-Methyl 2-[(4-bromo-2-formylphenoxy)methyl]-3-o-tolylacrylate

S. Vijayakumar,^a R. Madhanraj,^b S. Murugavel,^c ^* R. Selvakumar ^d and M. Bakthadoss ^d

^aDepartment of Physics, Sri Balaji Chokkalingam Engineering College, Arni, Thiruvannamalai 632 317, India, ^bDepartment of Physics, Ranipettai Engineering College, Thenkadapathangal, Walaja 632 513, India, ^cDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India, and ^dDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
^*Correspondence e-mail: smurugavel27@gmail.com

(Received 11 September 2011; accepted 15 September 2011; online 20 September 2011)

In the title compound, C₁₉H₁₇BrO₄, the dihedral angle between the two benzene rings is 82.1 (1)°. The molecular structure is stabilized by an intramolecular C—H⋯O hydrogen bond which generates an S(7) ring motif. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions. Intermolecular C—H⋯O interactions are involved in the formation of centrosymmetric R₂²(16) dimers, which are connected into supramolecular tapes running along the [100] direction.

Related literature

For background to the applications of acrylates, see: de Fraine et al. (1991 ); Zhang & Ji (1992 ). For related structures, see: Wang et al. (2011 ); Hou (2008 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₇BrO₄
M_r = 389.24
Triclinic, $[P \overline 1]$
a = 8.0114 (2) Å
b = 8.6138 (2) Å
c = 13.4827 (4) Å
α = 96.466 (1)°
β = 97.185 (1)°
γ = 106.546 (2)°
V = 874.08 (4) Å³
Z = 2
Mo Kα radiation
μ = 2.37 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.547, T_max = 0.653
21788 measured reflections
5440 independent reflections
2870 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.02
5440 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C13–C18 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3	0.93	2.59	3.377 (3)	143
C19—H19B⋯O1ⁱ	0.96	2.53	3.436 (3)	157
C5—H5⋯O4ⁱⁱ	0.93	2.44	3.273 (3)	149
C19—H19C⋯Cgⁱⁱⁱ	0.96	2.74	3.580 (3)	147
Symmetry codes: (i) -x+1, -y, -z; (ii) x+1, y, z; (iii) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811037731/bt5640sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811037731/bt5640Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811037731/bt5640Isup3.cml

checkCIF report

Comment top

Acrylate and its derivatives are important compounds because of their agrochemical and medical applications (de Fraine et al., 1991; Zhang & Ji, 1992).

Fig. 1. shows a displacement ellipsoid plot of the title compound with the atom numbering scheme. The dihedral angle between the two aromatic rings is 82.1 (1)°. The methyl acrylate (O1/O2/C7-C10) plane forms dihedral angles of 84.9 (1)° and 41.5 (1)°, respectively, with the bromo formyl phenyl and methyl phenyl rings. The geometric parameters of the title molecule agrees well with those reported for similar structures (Wang et al., 2011; Hou, 2008).

The molecular structure is stabilized by intramolecular C14—H14···O3 hydrogen bond which generates an S(7) ring motif. The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. The molecules at x, y, z and 1-x, -y, -z are linked by C19—H19B···O1 hydrogen bonds into cyclic centrosymmetric R₂²(16) dimers. The dimers are linked by the C5—H5···O4 hydrogen bond forming supramolecular tapes running along the [100] directions (Fig. 2). The crystal packing is further stabilized by C—H···π interactions between a methyl H19C atom and a neighbouring benzene ring (C13-C18), with a C19—H19C···Cgⁱⁱⁱ separation of 2.74 Å ( Fig. 3 and Table 1; Cg is the centroid of the C13-C18 benzene ring, Symmetry code as in Fig. 3).

Related literature top

For background to the applications of acrylates, see: de Fraine et al. (1991); Zhang & Ji (1992). For related structures, see: Wang et al. (2011); Hou (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A solution of salicylaldehyde (3.7 mmol, 0.74g) and potassium carbonate (5.59 mmol, 0.77g) in acetonitrile as solvent (10ml) was stirred for 15 minutes at room temperature. To this solution, (Z-methyl 2-(bromomethyl)-3-o-tolylacrylate (3.7 mmol, 1g) was added dropwise. After the completion of the reaction as indicated by TLC, acetonitrile was evaporated. Ethylacetate (15ml) and water (15ml) were added to the crude mass and extracted. The organic layer was dried over anhydrous sodium sulfate. Removal of the solvent led to the crude product which was purified through pad of silica gel (100-200 mesh) using ethylacetate and hexanes (1:9) as solvents. The pure title compound was obtained as a colorless solid (1.32g, 91%). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a ethylacetate solution at room temperature.

Structure description top

Acrylate and its derivatives are important compounds because of their agrochemical and medical applications (de Fraine et al., 1991; Zhang & Ji, 1992).

For background to the applications of acrylates, see: de Fraine et al. (1991); Zhang & Ji (1992). For related structures, see: Wang et al. (2011); Hou (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small cycles of arbitrary radius.
	Fig. 2. Supramolecular tape formation in the crystal packing of the title compound whereby centrosymmetrc R₂²(16) dimeric aggregates sustained by C—H···O (blue dashed lines) contacts are linked via C—H···O contacts (magenta dashed lines) along [1 0 0].
	Fig. 3. A view of the C-H···π interactions (dotted lines) in the crystal structure of the title compound. Cg denotes centroid of the C13-C18 benzene ring. [Symmetry code: (iii) 2-x, 1-y, -z.]

(Z)-Methyl 2-[(4-bromo-2-formylphenoxy)methyl]-3-o-tolylacrylate top

Crystal data top

C₁₉H₁₇BrO₄	Z = 2
M_r = 389.24	F(000) = 396
Triclinic, P1	D_x = 1.479 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0114 (2) Å	Cell parameters from 5491 reflections
b = 8.6138 (2) Å	θ = 1.5–30.8°
c = 13.4827 (4) Å	µ = 2.37 mm⁻¹
α = 96.466 (1)°	T = 293 K
β = 97.185 (1)°	Block, colourless
γ = 106.546 (2)°	0.25 × 0.23 × 0.18 mm
V = 874.08 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	5440 independent reflections
Radiation source: fine-focus sealed tube	2870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
Detector resolution: 10.0 pixels mm^-1	θ_max = 30.8°, θ_min = 2.5°
ω scans	h = −11→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −9→12
T_min = 0.547, T_max = 0.653	l = −19→19
21788 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0517P)² + 0.2207P] where P = (F_o² + 2F_c²)/3
5440 reflections	(Δ/σ)_max < 0.001
219 parameters	Δρ_max = 0.61 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₁₉H₁₇BrO₄	γ = 106.546 (2)°
M_r = 389.24	V = 874.08 (4) Å³
Triclinic, P1	Z = 2
a = 8.0114 (2) Å	Mo Kα radiation
b = 8.6138 (2) Å	µ = 2.37 mm⁻¹
c = 13.4827 (4) Å	T = 293 K
α = 96.466 (1)°	0.25 × 0.23 × 0.18 mm
β = 97.185 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5440 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2870 reflections with I > 2σ(I)
T_min = 0.547, T_max = 0.653	R_int = 0.025
21788 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.02	Δρ_max = 0.61 e Å⁻³
5440 reflections	Δρ_min = −0.61 e Å⁻³
219 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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.

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

	x	y	z	U_iso*/U_eq
C1	0.5938 (3)	0.6570 (2)	0.44131 (14)	0.0451 (4)
C2	0.6433 (3)	0.7625 (3)	0.53364 (16)	0.0582 (6)
H2	0.5581	0.7944	0.5644	0.070*
C3	0.8167 (4)	0.8193 (3)	0.57901 (16)	0.0628 (6)
C4	0.9439 (3)	0.7725 (3)	0.53421 (17)	0.0620 (6)
H4	1.0614	0.8124	0.5654	0.074*
C5	0.8989 (3)	0.6674 (3)	0.44374 (16)	0.0522 (5)
H5	0.9853	0.6360	0.4140	0.063*
C6	0.7237 (2)	0.6087 (2)	0.39719 (14)	0.0419 (4)
C7	0.7942 (2)	0.4478 (2)	0.26070 (15)	0.0460 (4)
H7A	0.8629	0.4046	0.3086	0.055*
H7B	0.8741	0.5375	0.2364	0.055*
C8	0.6943 (3)	0.3164 (2)	0.17415 (15)	0.0462 (4)
C9	0.6192 (3)	0.1482 (3)	0.19567 (16)	0.0514 (5)
C10	0.5959 (4)	−0.0215 (3)	0.3216 (2)	0.0829 (8)
H10A	0.4703	−0.0646	0.3009	0.124*
H10B	0.6242	−0.0147	0.3936	0.124*
H10C	0.6521	−0.0925	0.2885	0.124*
C11	0.4093 (3)	0.6015 (3)	0.39152 (18)	0.0588 (6)
H11	0.3784	0.5237	0.3333	0.071*
C12	0.6729 (3)	0.3375 (3)	0.07702 (15)	0.0494 (5)
H12	0.6170	0.2431	0.0304	0.059*
C13	0.7263 (2)	0.4903 (3)	0.03471 (15)	0.0490 (5)
C14	0.7153 (3)	0.6369 (3)	0.08434 (18)	0.0598 (5)
H14	0.6751	0.6385	0.1461	0.072*
C15	0.7630 (4)	0.7799 (3)	0.0434 (2)	0.0711 (7)
H15	0.7554	0.8770	0.0775	0.085*
C16	0.8218 (4)	0.7776 (3)	−0.0476 (2)	0.0743 (7)
H16	0.8566	0.8742	−0.0747	0.089*
C17	0.8297 (3)	0.6337 (3)	−0.09913 (18)	0.0651 (6)
H17	0.8673	0.6340	−0.1617	0.078*
C18	0.7828 (3)	0.4878 (3)	−0.06005 (15)	0.0531 (5)
C19	0.7942 (3)	0.3325 (3)	−0.11804 (17)	0.0655 (6)
H19A	0.8274	0.3532	−0.1824	0.098*
H19B	0.6814	0.2499	−0.1283	0.098*
H19C	0.8810	0.2951	−0.0804	0.098*
O1	0.5339 (3)	0.0321 (2)	0.13521 (13)	0.0794 (5)
O2	0.6575 (2)	0.13951 (18)	0.29434 (12)	0.0652 (4)
O3	0.66638 (17)	0.50451 (17)	0.30849 (10)	0.0497 (3)
O4	0.2955 (2)	0.6501 (3)	0.42096 (16)	0.0877 (6)
Br1	0.88459 (5)	0.96282 (4)	0.70416 (2)	0.10598 (18)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0500 (11)	0.0487 (11)	0.0443 (10)	0.0191 (9)	0.0157 (9)	0.0186 (8)
C2	0.0751 (16)	0.0628 (13)	0.0495 (11)	0.0316 (12)	0.0236 (11)	0.0185 (10)
C3	0.0861 (18)	0.0606 (13)	0.0405 (10)	0.0204 (12)	0.0117 (11)	0.0069 (9)
C4	0.0599 (13)	0.0636 (14)	0.0521 (12)	0.0087 (11)	−0.0021 (10)	0.0051 (10)
C5	0.0449 (11)	0.0578 (12)	0.0510 (11)	0.0123 (10)	0.0073 (9)	0.0060 (9)
C6	0.0445 (10)	0.0420 (10)	0.0391 (9)	0.0107 (8)	0.0080 (8)	0.0116 (8)
C7	0.0394 (10)	0.0467 (10)	0.0528 (11)	0.0139 (8)	0.0105 (8)	0.0051 (8)
C8	0.0423 (10)	0.0476 (11)	0.0491 (11)	0.0139 (9)	0.0104 (8)	0.0048 (8)
C9	0.0536 (12)	0.0490 (11)	0.0504 (11)	0.0142 (10)	0.0107 (9)	0.0035 (9)
C10	0.106 (2)	0.0545 (14)	0.0797 (18)	0.0085 (14)	0.0066 (15)	0.0254 (13)
C11	0.0498 (12)	0.0710 (14)	0.0669 (14)	0.0253 (11)	0.0187 (11)	0.0282 (12)
C12	0.0434 (10)	0.0529 (12)	0.0499 (11)	0.0135 (9)	0.0078 (9)	0.0027 (9)
C13	0.0396 (10)	0.0567 (12)	0.0482 (11)	0.0134 (9)	0.0021 (8)	0.0073 (9)
C14	0.0595 (13)	0.0647 (14)	0.0619 (13)	0.0268 (11)	0.0123 (11)	0.0137 (11)
C15	0.0777 (16)	0.0630 (15)	0.0803 (18)	0.0342 (13)	0.0083 (14)	0.0139 (13)
C16	0.0793 (17)	0.0678 (16)	0.0757 (17)	0.0188 (14)	0.0051 (14)	0.0284 (14)
C17	0.0607 (14)	0.0744 (16)	0.0530 (13)	0.0085 (12)	0.0033 (10)	0.0187 (12)
C18	0.0398 (10)	0.0650 (13)	0.0457 (11)	0.0067 (10)	−0.0025 (8)	0.0072 (10)
C19	0.0609 (14)	0.0723 (15)	0.0493 (12)	0.0043 (12)	0.0074 (10)	−0.0049 (11)
O1	0.1097 (14)	0.0511 (9)	0.0574 (9)	0.0001 (9)	0.0075 (9)	−0.0037 (8)
O2	0.0781 (11)	0.0482 (9)	0.0593 (9)	0.0066 (8)	−0.0001 (8)	0.0129 (7)
O3	0.0386 (7)	0.0575 (8)	0.0496 (8)	0.0131 (6)	0.0068 (6)	−0.0009 (6)
O4	0.0632 (11)	0.1185 (16)	0.1058 (15)	0.0513 (11)	0.0325 (10)	0.0350 (12)
Br1	0.1485 (4)	0.1068 (3)	0.05066 (17)	0.0334 (2)	0.00845 (17)	−0.01403 (15)

Geometric parameters (Å, º) top

C1—C2	1.396 (3)	C10—H10A	0.9600
C1—C6	1.398 (3)	C10—H10B	0.9600
C1—C11	1.464 (3)	C10—H10C	0.9600
C2—C3	1.370 (3)	C11—O4	1.197 (3)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.378 (3)	C12—C13	1.466 (3)
C3—Br1	1.895 (2)	C12—H12	0.9300
C4—C5	1.376 (3)	C13—C14	1.392 (3)
C4—H4	0.9300	C13—C18	1.408 (3)
C5—C6	1.387 (3)	C14—C15	1.380 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—O3	1.354 (2)	C15—C16	1.369 (4)
C7—O3	1.443 (2)	C15—H15	0.9300
C7—C8	1.496 (3)	C16—C17	1.373 (4)
C7—H7A	0.9700	C16—H16	0.9300
C7—H7B	0.9700	C17—C18	1.389 (3)
C8—C12	1.339 (3)	C17—H17	0.9300
C8—C9	1.478 (3)	C18—C19	1.504 (3)
C9—O1	1.191 (3)	C19—H19A	0.9600
C9—O2	1.343 (3)	C19—H19B	0.9600
C10—O2	1.440 (3)	C19—H19C	0.9600

C2—C1—C6	118.86 (19)	H10A—C10—H10C	109.5
C2—C1—C11	119.93 (19)	H10B—C10—H10C	109.5
C6—C1—C11	121.20 (19)	O4—C11—C1	124.1 (2)
C3—C2—C1	120.2 (2)	O4—C11—H11	117.9
C3—C2—H2	119.9	C1—C11—H11	117.9
C1—C2—H2	119.9	C8—C12—C13	128.39 (19)
C2—C3—C4	120.4 (2)	C8—C12—H12	115.8
C2—C3—Br1	120.44 (18)	C13—C12—H12	115.8
C4—C3—Br1	119.17 (19)	C14—C13—C18	119.1 (2)
C5—C4—C3	120.6 (2)	C14—C13—C12	121.34 (19)
C5—C4—H4	119.7	C18—C13—C12	119.46 (19)
C3—C4—H4	119.7	C15—C14—C13	121.1 (2)
C4—C5—C6	119.5 (2)	C15—C14—H14	119.4
C4—C5—H5	120.2	C13—C14—H14	119.4
C6—C5—H5	120.2	C16—C15—C14	119.5 (2)
O3—C6—C5	123.87 (17)	C16—C15—H15	120.2
O3—C6—C1	115.80 (17)	C14—C15—H15	120.2
C5—C6—C1	120.33 (18)	C15—C16—C17	120.4 (2)
O3—C7—C8	107.34 (15)	C15—C16—H16	119.8
O3—C7—H7A	110.2	C17—C16—H16	119.8
C8—C7—H7A	110.2	C16—C17—C18	121.5 (2)
O3—C7—H7B	110.2	C16—C17—H17	119.2
C8—C7—H7B	110.2	C18—C17—H17	119.2
H7A—C7—H7B	108.5	C17—C18—C13	118.2 (2)
C12—C8—C9	116.79 (19)	C17—C18—C19	120.2 (2)
C12—C8—C7	124.91 (19)	C13—C18—C19	121.5 (2)
C9—C8—C7	118.25 (18)	C18—C19—H19A	109.5
O1—C9—O2	122.5 (2)	C18—C19—H19B	109.5
O1—C9—C8	125.9 (2)	H19A—C19—H19B	109.5
O2—C9—C8	111.64 (18)	C18—C19—H19C	109.5
O2—C10—H10A	109.5	H19A—C19—H19C	109.5
O2—C10—H10B	109.5	H19B—C19—H19C	109.5
H10A—C10—H10B	109.5	C9—O2—C10	115.46 (19)
O2—C10—H10C	109.5	C6—O3—C7	118.17 (15)

C6—C1—C2—C3	1.0 (3)	C9—C8—C12—C13	177.09 (19)
C11—C1—C2—C3	−177.82 (19)	C7—C8—C12—C13	−5.6 (3)
C1—C2—C3—C4	−0.2 (3)	C8—C12—C13—C14	−37.2 (3)
C1—C2—C3—Br1	179.89 (15)	C8—C12—C13—C18	145.6 (2)
C2—C3—C4—C5	−0.5 (4)	C18—C13—C14—C15	−1.7 (3)
Br1—C3—C4—C5	179.47 (17)	C12—C13—C14—C15	−179.0 (2)
C3—C4—C5—C6	0.3 (3)	C13—C14—C15—C16	0.2 (4)
C4—C5—C6—O3	−179.72 (19)	C14—C15—C16—C17	1.4 (4)
C4—C5—C6—C1	0.5 (3)	C15—C16—C17—C18	−1.5 (4)
C2—C1—C6—O3	179.09 (17)	C16—C17—C18—C13	0.0 (3)
C11—C1—C6—O3	−2.1 (3)	C16—C17—C18—C19	−179.6 (2)
C2—C1—C6—C5	−1.2 (3)	C14—C13—C18—C17	1.5 (3)
C11—C1—C6—C5	177.62 (19)	C12—C13—C18—C17	178.89 (19)
O3—C7—C8—C12	100.2 (2)	C14—C13—C18—C19	−178.89 (19)
O3—C7—C8—C9	−82.5 (2)	C12—C13—C18—C19	−1.5 (3)
C12—C8—C9—O1	−4.1 (3)	O1—C9—O2—C10	2.9 (3)
C7—C8—C9—O1	178.4 (2)	C8—C9—O2—C10	−177.5 (2)
C12—C8—C9—O2	176.27 (18)	C5—C6—O3—C7	1.6 (3)
C7—C8—C9—O2	−1.2 (3)	C1—C6—O3—C7	−178.66 (16)
C2—C1—C11—O4	5.7 (3)	C8—C7—O3—C6	171.39 (15)
C6—C1—C11—O4	−173.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.59	3.377 (3)	143
C19—H19B···O1ⁱ	0.96	2.53	3.436 (3)	157
C5—H5···O4ⁱⁱ	0.93	2.44	3.273 (3)	149
C19—H19C···Cgⁱⁱⁱ	0.96	2.74	3.580 (3)	147

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇BrO₄
M_r	389.24
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.0114 (2), 8.6138 (2), 13.4827 (4)
α, β, γ (°)	96.466 (1), 97.185 (1), 106.546 (2)
V (Å³)	874.08 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.37
Crystal size (mm)	0.25 × 0.23 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.547, 0.653
No. of measured, independent and observed [I > 2σ(I)] reflections	21788, 5440, 2870
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.721

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 1.02
No. of reflections	5440
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.61

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.59	3.377 (3)	143
C19—H19B···O1ⁱ	0.96	2.53	3.436 (3)	157
C5—H5···O4ⁱⁱ	0.93	2.44	3.273 (3)	149
C19—H19C···Cgⁱⁱⁱ	0.96	2.74	3.580 (3)	147

Symmetry codes: (i) −x+1, −y, −z; (ii) x+1, y, z; (iii) −x+2, −y+1, −z.

Acknowledgements

SM thanks Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

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
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fraine, P. J. de & Martin, A. (1991). US Patent 5 055 471. Google Scholar
Hou, J. (2008). Acta Cryst. E64, o2293. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). 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
Wang, L., Meng, F.-Y., Lin, C.-W., Chen, H.-Y. & Luo, X. (2011). Acta Cryst. E67, o354. Web of Science CSD CrossRef IUCr Journals Google Scholar
Zhang, L. P. & Ji, Z. Z. (1992). Acta Pharmacol. Sin. 27, 817–823. CAS Google Scholar