Methyl (Z)-2-[(4-bromo-2-formyl­phen­oxy)meth­yl]-3-(4-methyl­phen­yl)acrylate

Vijayakumar, S.; Murugavel, S.; Kannan, D.; Bakthadoss, M.

doi:10.1107/S1600536812006630

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o775

doi:10.1107/S1600536812006630

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Methyl (Z)-2-[(4-bromo-2-formylphenoxy)methyl]-3-(4-methylphenyl)acrylate

S. Vijayakumar,^a S. Murugavel,^b ^* D. Kannan ^c and M. Bakthadoss ^c ‡

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

(Received 12 February 2012; accepted 14 February 2012; online 17 February 2012)

In the title compound, C₁₉H₁₇BrO₄, the dihedral angle between the two benzene rings is 82.9 (2)°. 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 C—H⋯O hydrogen bonds, which generate two centrosymmetic ring systems with R₂²(18) and R₂²(14) graph-set motifs. The crystal packing is further stabilized by intermolecular π–π interactions [centroid–centroid distance = 3.984 (2) Å].

Related literature

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

Experimental

Crystal data

C₁₉H₁₇BrO₄
M_r = 389.24
Triclinic, $[P \overline 1]$
a = 7.9262 (4) Å
b = 8.9078 (5) Å
c = 13.2331 (6) Å
α = 74.387 (3)°
β = 83.593 (2)°
γ = 75.770 (3)°
V = 871.20 (8) Å³
Z = 2
Mo Kα radiation
μ = 2.38 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 = 0.546, T_max = 0.652
15446 measured reflections
3386 independent reflections
2419 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.121
S = 1.01
3386 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O3	0.93	2.55	3.341 (3)	143
C4—H4⋯O2ⁱ	0.93	2.57	3.474 (4)	164
C18—H18⋯O1ⁱⁱ	0.93	2.49	3.388 (4)	161
C5—H5⋯O4ⁱⁱⁱ	0.93	2.39	3.276 (4)	159
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y-1, -z+1; (iii) x+1, y, 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: 10.1107/S1600536812006630/bt5816sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006630/bt5816Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006630/bt5816Isup3.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). We report herein the crystal structure of the title compound, (I).

Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The dihedral angle between the two benzene rings is 82.9 (2)°. The methyl acrylate (O1/O2/C7—C10) plane forms dihedral angles of 87.9 (1)° and 32.6 (1)° respectively, with the bromo formyl phenyl and methyl phenyl rings. The bromine atom deviates from the plane of the attached ring by -0.011 (1) Å. The geometric parameters of the title molecule agrees well with those reported for similar structures (Wang et al., 2011, Vijayakumar et al., 2011).

The molecular structure is stabilized by an intramolecular C14—H14···O3 hydrogen bond which generates an S(7) ring motif (Bernstein et al., 1995) (Table 1). The crystal packing is stabilized by intermolecular C—H···O hydrogen bonds. The formation of the framework can be explained in terms of two-one substructures. In the first substructure C4—H4···O2 at (x, y, z and 1 - x, -y, -z) and C18—H18···O1 at (x, y, z and 1 - x, -1 - y, 1 - z) hydrogen bonding interactions form a cyclic centrosymmetric pattern, with the graph set motif R₂²(18) and R₂²(14), respectively. These combine to form zigzag chains which propagate along [001] (Fig. 2). In the second substructure, atom C5 in the molecule at (x, y, z) acts as a hydrogen bond donor to atom O4 in the molecule at (1 + x, y, z) generating C(6) chains which are running along [100] (Fig. 3). The crystal packing is further stabilized by an intermolecular π—π interactions with Cg—Cgⁱ separation of 3.984 (2) Å (Fig. 4; Cg is the centroid of the (C13–C18) benzene ring).

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); Vijayakumar et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

A solution of 5-bromo-2-hydroxybenzaldehyde (1.0 mmol, 0.201 g) and potassium carbonate (1.5 mmol, 0.207 g) in acetonitrile solvent (10 ml) was stirred for 15 minutes at room temperature. To this solution, (Z-methyl 2-(bromomethyl)-3-p-tolylacrylate (1.2 mmol, 0.324 g) was added dropwise till the addition is complete. After the completion of the reaction as indicated by TLC, acetonitrile was evaporated. Ethylacetate (15 ml) and water (15 ml) were added to the crude mass and extracted. The organic layer was dried over anhydrous sodium sulfate. Removal of 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 (0.350 g, 90% yield). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a ethylacetate solution at room temperature.

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 spheres of arbitrary radius.
	Fig. 2. Part of the crystal structure of (I) showing C—H···O hydrogen bonds generating R₂²(18)(Red dotted lines) and R₂²(14) (blue dotted lines) centrosymmetric dimers, forming zigzag chains along [001]. [Symmetry codes:(i)1 - x, -y, -z; (ii)1 - x, -1 - y, 1 - z; (iii)x, -1 + y, 1 + z; (iv)1 - x, -2 - y, 2 - z].
	Fig. 3. Part of the crystal structure of (I) showing C—H···O hydrogen bonds (blue dotted lines), with the formation of C(6) chains along [100]. [Symmetry codes: (i)1 + x, y, z; (ii)2 + x, y, z; (iii) 3 + x, y, z].
	Fig. 4. A view of the π—π interaction (dotted line) in the crystal structure of the title compound. Cg denotes centroid of the C13–C18 benzene ring. [Symmetry code: (i)-x, -y, 1 - z].

Methyl (Z)-2-[(4-bromo-2-formylphenoxy)methyl]- 3-(4-methylphenyl)acrylate top

Crystal data top

C₁₉H₁₇BrO₄	Z = 2
M_r = 389.24	F(000) = 396
Triclinic, P1	D_x = 1.484 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9262 (4) Å	Cell parameters from 3452 reflections
b = 8.9078 (5) Å	θ = 1.6–26.1°
c = 13.2331 (6) Å	µ = 2.38 mm⁻¹
α = 74.387 (3)°	T = 293 K
β = 83.593 (2)°	Block, colourless
γ = 75.770 (3)°	0.25 × 0.23 × 0.18 mm
V = 871.20 (8) Å³

Data collection top

Bruker APEXII CCD diffractometer	3386 independent reflections
Radiation source: fine-focus sealed tube	2419 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.1°, θ_min = 2.4°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
T_min = 0.546, T_max = 0.652	l = −16→16
15446 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0704P)² + 0.2283P] where P = (F_o² + 2F_c²)/3
3386 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₉H₁₇BrO₄	γ = 75.770 (3)°
M_r = 389.24	V = 871.20 (8) Å³
Triclinic, P1	Z = 2
a = 7.9262 (4) Å	Mo Kα radiation
b = 8.9078 (5) Å	µ = 2.38 mm⁻¹
c = 13.2331 (6) Å	T = 293 K
α = 74.387 (3)°	0.25 × 0.23 × 0.18 mm
β = 83.593 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3386 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2419 reflections with I > 2σ(I)
T_min = 0.546, T_max = 0.652	R_int = 0.038
15446 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.01	Δρ_max = 0.67 e Å⁻³
3386 reflections	Δρ_min = −0.41 e Å⁻³
219 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
C1	−0.0190 (3)	0.1409 (3)	0.0632 (2)	0.0436 (6)
C2	−0.0529 (4)	0.2719 (3)	−0.0228 (2)	0.0492 (7)
H2	−0.1652	0.3118	−0.0466	0.059*
C3	0.0793 (4)	0.3418 (3)	−0.0723 (2)	0.0530 (8)
C4	0.2463 (4)	0.2851 (3)	−0.0381 (2)	0.0521 (7)
H4	0.3347	0.3345	−0.0727	0.063*
C5	0.2831 (4)	0.1550 (3)	0.0472 (2)	0.0476 (7)
H5	0.3958	0.1169	0.0706	0.057*
C6	0.1509 (3)	0.0820 (3)	0.0978 (2)	0.0400 (6)
C7	0.3452 (3)	−0.1066 (3)	0.2212 (2)	0.0463 (7)
H7A	0.3805	−0.0227	0.2418	0.056*
H7B	0.4283	−0.1395	0.1673	0.056*
C8	0.3425 (4)	−0.2459 (3)	0.3141 (2)	0.0491 (7)
C9	0.3846 (4)	−0.4096 (4)	0.2990 (3)	0.0568 (8)
C10	0.4617 (6)	−0.5711 (5)	0.1796 (3)	0.0814 (11)
H10A	0.5751	−0.6240	0.2056	0.122*
H10B	0.4643	−0.5618	0.1055	0.122*
H10C	0.3785	−0.6322	0.2151	0.122*
C11	−0.1608 (4)	0.0680 (4)	0.1180 (3)	0.0555 (8)
H11	−0.1325	−0.0241	0.1721	0.067*
C12	0.3161 (4)	−0.2336 (4)	0.4127 (2)	0.0556 (8)
H12	0.3271	−0.3307	0.4630	0.067*
C13	0.2727 (4)	−0.0931 (4)	0.4554 (2)	0.0512 (7)
C14	0.1771 (4)	0.0561 (4)	0.4051 (2)	0.0577 (8)
H14	0.1347	0.0708	0.3395	0.069*
C15	0.1444 (4)	0.1815 (4)	0.4507 (3)	0.0638 (9)
H15	0.0807	0.2805	0.4151	0.077*
C16	0.2035 (4)	0.1652 (4)	0.5481 (3)	0.0613 (8)
C17	0.2973 (4)	0.0179 (4)	0.5982 (3)	0.0651 (9)
H17	0.3392	0.0042	0.6637	0.078*
C18	0.3305 (4)	−0.1087 (4)	0.5544 (3)	0.0627 (8)
H18	0.3929	−0.2076	0.5911	0.075*
C19	0.1688 (6)	0.3035 (5)	0.5977 (3)	0.0875 (12)
H19A	0.1914	0.2644	0.6711	0.131*
H19B	0.0493	0.3601	0.5898	0.131*
H19C	0.2435	0.3744	0.5641	0.131*
Br1	0.03444 (6)	0.52045 (4)	−0.19017 (3)	0.0788 (2)
O1	0.3943 (5)	−0.5289 (3)	0.3685 (2)	0.0984 (9)
O2	0.4125 (3)	−0.4137 (3)	0.19867 (17)	0.0616 (6)
O3	0.1745 (2)	−0.0481 (2)	0.18098 (15)	0.0472 (5)
O4	−0.3117 (3)	0.1191 (3)	0.0979 (2)	0.0792 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0456 (16)	0.0445 (15)	0.0437 (15)	−0.0063 (12)	−0.0056 (12)	−0.0183 (12)
C2	0.0560 (17)	0.0468 (16)	0.0461 (16)	−0.0008 (14)	−0.0123 (14)	−0.0195 (13)
C3	0.079 (2)	0.0398 (15)	0.0375 (15)	−0.0019 (15)	−0.0099 (15)	−0.0129 (12)
C4	0.0628 (19)	0.0461 (16)	0.0462 (16)	−0.0129 (14)	0.0038 (14)	−0.0114 (13)
C5	0.0452 (16)	0.0483 (16)	0.0493 (16)	−0.0105 (13)	−0.0031 (13)	−0.0121 (13)
C6	0.0464 (16)	0.0381 (14)	0.0377 (13)	−0.0084 (12)	−0.0045 (12)	−0.0131 (11)
C7	0.0401 (15)	0.0445 (16)	0.0497 (16)	−0.0047 (12)	−0.0049 (12)	−0.0076 (13)
C8	0.0465 (16)	0.0432 (16)	0.0522 (17)	−0.0058 (12)	−0.0060 (13)	−0.0053 (13)
C9	0.065 (2)	0.0443 (17)	0.0537 (18)	−0.0052 (14)	−0.0029 (15)	−0.0060 (14)
C10	0.105 (3)	0.060 (2)	0.082 (3)	−0.013 (2)	−0.005 (2)	−0.029 (2)
C11	0.0481 (19)	0.061 (2)	0.0616 (19)	−0.0093 (15)	−0.0014 (15)	−0.0259 (16)
C12	0.0605 (19)	0.0479 (17)	0.0505 (18)	−0.0071 (14)	−0.0080 (14)	−0.0016 (14)
C13	0.0554 (18)	0.0500 (17)	0.0438 (16)	−0.0113 (14)	0.0004 (13)	−0.0060 (13)
C14	0.064 (2)	0.0572 (19)	0.0470 (17)	−0.0053 (15)	−0.0085 (15)	−0.0100 (14)
C15	0.075 (2)	0.0523 (19)	0.0557 (19)	−0.0021 (16)	−0.0047 (16)	−0.0106 (15)
C16	0.064 (2)	0.066 (2)	0.0539 (19)	−0.0175 (17)	0.0086 (16)	−0.0187 (16)
C17	0.068 (2)	0.083 (3)	0.0450 (17)	−0.0144 (18)	−0.0014 (15)	−0.0196 (17)
C18	0.067 (2)	0.064 (2)	0.0445 (17)	−0.0026 (16)	−0.0013 (15)	−0.0045 (15)
C19	0.105 (3)	0.088 (3)	0.078 (3)	−0.020 (2)	0.006 (2)	−0.040 (2)
Br1	0.1216 (4)	0.0559 (3)	0.0471 (2)	−0.0034 (2)	−0.01539 (19)	−0.00359 (15)
O1	0.167 (3)	0.0439 (14)	0.0661 (16)	−0.0054 (15)	−0.0002 (17)	−0.0025 (12)
O2	0.0770 (15)	0.0477 (12)	0.0569 (13)	−0.0091 (10)	−0.0040 (11)	−0.0118 (10)
O3	0.0432 (11)	0.0475 (11)	0.0476 (11)	−0.0118 (8)	−0.0073 (8)	−0.0031 (9)
O4	0.0420 (13)	0.098 (2)	0.101 (2)	−0.0105 (12)	−0.0076 (13)	−0.0351 (16)

Geometric parameters (Å, º) top

C1—C2	1.388 (4)	C10—H10A	0.9600
C1—C6	1.399 (4)	C10—H10B	0.9600
C1—C11	1.461 (4)	C10—H10C	0.9600
C2—C3	1.365 (4)	C11—O4	1.203 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.376 (4)	C12—C13	1.459 (4)
C3—Br1	1.898 (3)	C12—H12	0.9300
C4—C5	1.381 (4)	C13—C14	1.387 (4)
C4—H4	0.9300	C13—C18	1.396 (4)
C5—C6	1.383 (4)	C14—C15	1.366 (5)
C5—H5	0.9300	C14—H14	0.9300
C6—O3	1.357 (3)	C15—C16	1.380 (5)
C7—O3	1.432 (3)	C15—H15	0.9300
C7—C8	1.496 (4)	C16—C17	1.369 (5)
C7—H7A	0.9700	C16—C19	1.501 (5)
C7—H7B	0.9700	C17—C18	1.360 (5)
C8—C12	1.328 (4)	C17—H17	0.9300
C8—C9	1.477 (4)	C18—H18	0.9300
C9—O1	1.196 (4)	C19—H19A	0.9600
C9—O2	1.330 (4)	C19—H19B	0.9600
C10—O2	1.442 (4)	C19—H19C	0.9600

C2—C1—C6	119.4 (3)	H10A—C10—H10C	109.5
C2—C1—C11	120.0 (3)	H10B—C10—H10C	109.5
C6—C1—C11	120.6 (3)	O4—C11—C1	124.4 (3)
C3—C2—C1	119.7 (3)	O4—C11—H11	117.8
C3—C2—H2	120.1	C1—C11—H11	117.8
C1—C2—H2	120.1	C8—C12—C13	130.8 (3)
C2—C3—C4	121.1 (3)	C8—C12—H12	114.6
C2—C3—Br1	120.1 (2)	C13—C12—H12	114.6
C4—C3—Br1	118.9 (2)	C14—C13—C18	117.1 (3)
C3—C4—C5	120.2 (3)	C14—C13—C12	124.8 (3)
C3—C4—H4	119.9	C18—C13—C12	118.1 (3)
C5—C4—H4	119.9	C15—C14—C13	120.8 (3)
C4—C5—C6	119.5 (3)	C15—C14—H14	119.6
C4—C5—H5	120.3	C13—C14—H14	119.6
C6—C5—H5	120.3	C14—C15—C16	121.7 (3)
O3—C6—C5	123.9 (2)	C14—C15—H15	119.1
O3—C6—C1	116.0 (2)	C16—C15—H15	119.1
C5—C6—C1	120.1 (3)	C17—C16—C15	117.6 (3)
O3—C7—C8	109.0 (2)	C17—C16—C19	120.8 (3)
O3—C7—H7A	109.9	C15—C16—C19	121.7 (3)
C8—C7—H7A	109.9	C18—C17—C16	121.6 (3)
O3—C7—H7B	109.9	C18—C17—H17	119.2
C8—C7—H7B	109.9	C16—C17—H17	119.2
H7A—C7—H7B	108.3	C17—C18—C13	121.2 (3)
C12—C8—C9	116.4 (3)	C17—C18—H18	119.4
C12—C8—C7	123.8 (3)	C13—C18—H18	119.4
C9—C8—C7	119.6 (3)	C16—C19—H19A	109.5
O1—C9—O2	121.9 (3)	C16—C19—H19B	109.5
O1—C9—C8	124.7 (3)	H19A—C19—H19B	109.5
O2—C9—C8	113.4 (3)	C16—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	115.7 (3)
O2—C10—H10C	109.5	C6—O3—C7	117.3 (2)

C6—C1—C2—C3	−0.2 (4)	C6—C1—C11—O4	174.2 (3)
C11—C1—C2—C3	178.5 (3)	C9—C8—C12—C13	−180.0 (3)
C1—C2—C3—C4	−0.3 (4)	C7—C8—C12—C13	5.0 (5)
C1—C2—C3—Br1	179.79 (19)	C8—C12—C13—C14	30.2 (5)
C2—C3—C4—C5	0.2 (4)	C8—C12—C13—C18	−150.1 (3)
Br1—C3—C4—C5	−179.8 (2)	C18—C13—C14—C15	1.0 (5)
C3—C4—C5—C6	0.3 (4)	C12—C13—C14—C15	−179.3 (3)
C4—C5—C6—O3	178.7 (3)	C13—C14—C15—C16	−0.4 (5)
C4—C5—C6—C1	−0.7 (4)	C14—C15—C16—C17	0.1 (5)
C2—C1—C6—O3	−178.8 (2)	C14—C15—C16—C19	179.5 (3)
C11—C1—C6—O3	2.5 (4)	C15—C16—C17—C18	−0.5 (5)
C2—C1—C6—C5	0.7 (4)	C19—C16—C17—C18	−179.8 (3)
C11—C1—C6—C5	−178.0 (3)	C16—C17—C18—C13	1.1 (5)
O3—C7—C8—C12	−93.5 (3)	C14—C13—C18—C17	−1.4 (5)
O3—C7—C8—C9	91.6 (3)	C12—C13—C18—C17	178.9 (3)
C12—C8—C9—O1	0.9 (5)	O1—C9—O2—C10	−2.4 (5)
C7—C8—C9—O1	176.2 (3)	C8—C9—O2—C10	177.4 (3)
C12—C8—C9—O2	−178.9 (3)	C5—C6—O3—C7	3.3 (4)
C7—C8—C9—O2	−3.6 (4)	C1—C6—O3—C7	−177.2 (2)
C2—C1—C11—O4	−4.5 (4)	C8—C7—O3—C6	178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O3	0.93	2.55	3.341 (3)	143
C4—H4···O2ⁱ	0.93	2.57	3.474 (4)	164
C18—H18···O1ⁱⁱ	0.93	2.49	3.388 (4)	161
C5—H5···O4ⁱⁱⁱ	0.93	2.39	3.276 (4)	159

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y−1, −z+1; (iii) x+1, y, 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)	7.9262 (4), 8.9078 (5), 13.2331 (6)
α, β, γ (°)	74.387 (3), 83.593 (2), 75.770 (3)
V (Å³)	871.20 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.38
Crystal size (mm)	0.25 × 0.23 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.546, 0.652
No. of measured, independent and observed [I > 2σ(I)] reflections	15446, 3386, 2419
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.121, 1.01
No. of reflections	3386
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.41

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	2.55	3.341 (3)	143.0
C4—H4···O2ⁱ	0.93	2.57	3.474 (4)	163.9
C18—H18···O1ⁱⁱ	0.93	2.49	3.388 (4)	161.4
C5—H5···O4ⁱⁱⁱ	0.93	2.39	3.276 (4)	158.6

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

Footnotes

‡Additional correspondence author, e-mail: bhakthadoss@yahoo.com.

Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

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