organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Methyl (2Z)-2-bromo­meth­yl-3-(3-chloro­phen­yl)prop-2-enoate

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 6 April 2013; accepted 3 May 2013; online 11 May 2013)

There are two independent mol­ecules (A and B) in the asymmetric unit of the title compound C11H10BrClO2, which represents the Z isomer. The methyl­acrylate moieties are essentially planar, within 0.084 (2) and 0.027 (5) Å in mol­ecules A and B, respectively. The benzene ring makes dihedral angles of 13.17 (7) and 27.89 (9)° with the methyl­acrylate moiety in mol­ecules A and B, respectively. The methyl­bromide moiety is almost orthogonal to the benzene ring, making dihedral angles of 81.46 (16)° in mol­ecule A and 79.61 (16)° in mol­ecule B. The methyl­acrylate moiety exhibits an extended trans conformation in both mol­ecules. In the crystal, pairs of C—H⋯O hydrogen bonds result in the formation of quasi-centrosymmetric R22(14) AB dimers.

Related literature

For the uses of cinnamic acid and its derivatives, see: De et al. (2011[De, P., Baltas, M. & Bedos-Belval, F. (2011). Curr. Med. Chem. 18, 1672-1703.]); Sharma (2011[Sharma, P. (2011). J. Chem. Pharm. Res. 3, 403-423.]). For an extended acrylate conformation, see: Schweizer & Dunitz (1982[Schweizer, W. B. & Dunitz, J. D. (1982). Helv. Chim. Acta, 65, 1547-1554.]). For a related structure, see: Swaminathan et al. (2013[Swaminathan, K., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2013). Acta Cryst. E69, o572.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.])

[Scheme 1]

Experimental

Crystal data
  • C11H10BrClO2

  • Mr = 289.54

  • Triclinic, [P \overline 1]

  • a = 7.4523 (3) Å

  • b = 11.7003 (4) Å

  • c = 14.3121 (5) Å

  • α = 72.078 (2)°

  • β = 76.539 (2)°

  • γ = 76.773 (2)°

  • V = 1137.98 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.82 mm−1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]) Tmin = 0.330, Tmax = 0.466

  • 27124 measured reflections

  • 6597 independent reflections

  • 4205 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.036

  • wR(F2) = 0.092

  • S = 1.00

  • 6597 reflections

  • 273 parameters

  • H-atom parameters constrained

  • Δρmax = 0.85 e Å−3

  • Δρmin = −0.49 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C1A—H1A⋯O1Bi 0.93 2.53 3.429 (3) 161
C1B—H1B⋯O1Ai 0.93 2.51 3.380 (3) 156
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Cinnamic acid derivatives are naturally occurring substances found in fruits, vegetables, flowers etc. and are consumed as dietary phenolic compounds. Different substitutions on basic moiety lead to various pharmacological activities like antioxidant, hepatoprotective, anxiolytic, insect repellent, antidiabetic, anticholesterolemic etc. (Sharma, 2011). Cinnamic acid derivatives received much attention in medicinal research as traditional as well as recent synthetic antitumor agents. (De et al., 2011).

X-ray analysis established the molecular structure and atom connectivity of the title compound C11H10BrClO2, as illustrated in Fig. 1. The title compound comprises two crystallographically independent molecules in the asymmetric unit. The corresponding bond lengths and bond angles of both the molecules agree well with each other.

The methylacrylate moiety is essentially planar with a maximum deviation of 0.0843 (23) Å for atom C7A in the molecule A and 0.0271 (50) Å for atom C10B in the molecule B. Also the least square planes of the methylacrylate moiety form dihedral angles of 13.17 (7)° and 27.89 (9)°, with the least square planes of the respective benzene rings, in the molecules A and B, respectively.

The methylacrylate moieties adopt an extended conformation, as evident from the torsion angle values: [C7A–C8A–C9A–O1A = 11.0 (3)°, C7A–C8A–C9A–O2A = -170.21 (19)°, C8A–C9A–O2A–C10A = -179.1 (2)° and O1A–C9A–O2A–C10A = -0.3 (3)°] for the molecule A and [C7B–C8B–C9B–O1B = -2.9 (3)°, C7B–C8B–C9B–O2B = 177.7 (2)°, C8B–C9B–O2B–C10B = -179.1 (2)° and O1B–C9B–O2B–C10B = 0.7 (4)°] for the molecule B. The reasons for the extended conformation were discussed earlier (Schweizer and Dunitz, 1982).

In the molecule A, the phenyl ring and the carbonyl group of the acrylate are (+)syn-periplanar to each other with the torsion angle of C7A–C8A–C9A–O1A = 11.0 (3)° whereas in the molecule B, they are (-)syn-periplanar to each other with the torsion angle of C7B–C8B–C9B–O1B = -2.9 (3)°. Likewise, the carbonyl group of the acrylate and the methylbromide group are (-)anti-periplanar to each other with the torsion angle of C11A–C8A–C9A–O1A = -165.5 (2)°, in the molecule A while they are (+)anti-periplanar to each other with the torsion angle of C11B–C8B–C9B–O1B = 172.4 (2)°, in the molecule B.

The least square plane of methylbromide group in the molecule A, forms dihedral angles of 81.46 (16) and 85.04 (13)° with the phenyl ring and the acrylate group, respectively, being almost orthogonal to both. Similarly, the least square plane of methyl bromide group in the molecule B, forms dihedral angles of 79.61 (16) and 81.51 (16)° with the phenyl ring and the acrylate group, respectively, being nearly orthogonal to both. The title compound exhibits structural similarities with a related structure reported earlier (Swaminathan et al. 2013).

The crystal packing is stabilized by intermolecular C1A—H1A···O1Bi and C1B—H1B···O1Ai hydrogen bonds which form quasi-centrosymmetric R22(14) dimers. The symmetry code: (i) -x + 1,-y + 1,-z + 1. The packing view of the title compound is shown in Fig.2.

Related literature top

For the uses of cinnamic acid and its derivatives, see: De et al. (2011); Sharma (2011). For an extended acrylate conformation, see: Schweizer & Dunitz (1982). For a related structure, see: Swaminathan et al. (2013). For graph-set notation, see: Bernstein et al.(1995)

Experimental top

To a stirred solution of methyl 2-((3-chlorophenyl)(hydroxy)methyl) acrylate (4 mmol) in CH2Cl2 (15 ml), 48% aqueous HBr (0.68 ml) was added at room temperature. The reaction mixture was cooled to 273 K and then catalytic amount of concentrated H2SO4 was added dropwise. The reaction mixture was stirred well at room temperature for about 24 hrs. After the completion of the reaction (confirmed by TLC analysis), the reaction mixture was poured into water and the aqueous layer was extracted with ethyl acetate (3 x 10 ml). The combined organic layer was washed with brine (10 ml) and concentrated. The crude product thus obtained was purified by column chromatography (EtOAc/Hexane, 2–6%) to provide Methyl (2Z)-2-(bromomethyl)-3-(3-chlorophenyl)prop-2-enoate in 90% yield, as a yellow crystalline solid.

Refinement top

Hydrogen atoms were placed in calculated positions with C—H = 0.93 - 0.97 Å and refined in riding model with fixed isotropic displacement parameters: Uiso(H) = 1.2 Ueq(C) for aromatic and methylene groups Uiso(H) = 1.5 Ueq(O) for methyl group. The rotation angles for methyl group were optimized by least squares.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at 30% probability level. H atoms are present as small spheres of arbitary radius.
[Figure 2] Fig. 2. The crystal structure of the title compound, showing the formation of quasi-centrosymmetric R22(14) dimers. Hydrogen bonds are shown as dotted lines. The hydrogen atoms not involved in bonding have been omitted for the sake of clarity.
Methyl (2Z)-2-bromomethyl-3-(3-chlorophenyl)prop-2-enoate top
Crystal data top
C11H10BrClO2Z = 4
Mr = 289.54F(000) = 576
Triclinic, P1Dx = 1.690 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.4523 (3) ÅCell parameters from 4205 reflections
b = 11.7003 (4) Åθ = 2.7–30.0°
c = 14.3121 (5) ŵ = 3.82 mm1
α = 72.078 (2)°T = 296 K
β = 76.539 (2)°Block, colourless
γ = 76.773 (2)°0.30 × 0.25 × 0.20 mm
V = 1137.98 (7) Å3
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6597 independent reflections
Radiation source: fine-focus sealed tube4205 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω & ϕ scansθmax = 30.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 108
Tmin = 0.330, Tmax = 0.466k = 1616
27124 measured reflectionsl = 2019
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0394P)2 + 0.4208P]
where P = (Fo2 + 2Fc2)/3
6597 reflections(Δ/σ)max < 0.001
273 parametersΔρmax = 0.85 e Å3
0 restraintsΔρmin = 0.49 e Å3
Crystal data top
C11H10BrClO2γ = 76.773 (2)°
Mr = 289.54V = 1137.98 (7) Å3
Triclinic, P1Z = 4
a = 7.4523 (3) ÅMo Kα radiation
b = 11.7003 (4) ŵ = 3.82 mm1
c = 14.3121 (5) ÅT = 296 K
α = 72.078 (2)°0.30 × 0.25 × 0.20 mm
β = 76.539 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6597 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
4205 reflections with I > 2σ(I)
Tmin = 0.330, Tmax = 0.466Rint = 0.032
27124 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.00Δρmax = 0.85 e Å3
6597 reflectionsΔρmin = 0.49 e Å3
273 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
xyzUiso*/Ueq
C1A0.2876 (3)0.7438 (2)0.31195 (17)0.0375 (5)
H1A0.30900.75710.36900.045*
C1B0.7397 (3)0.6245 (2)0.15677 (18)0.0427 (5)
H1B0.74680.64130.21510.051*
C2A0.2785 (3)0.8381 (2)0.22676 (18)0.0427 (5)
C2B0.7449 (3)0.7153 (2)0.06871 (19)0.0471 (6)
C3A0.2509 (4)0.8220 (3)0.14019 (19)0.0520 (6)
H3A0.24410.88690.08320.062*
C3B0.7299 (4)0.6945 (3)0.0185 (2)0.0535 (7)
H3B0.73250.75680.07750.064*
C4A0.2337 (4)0.7075 (3)0.13990 (19)0.0535 (7)
H4A0.21810.69470.08150.064*
C4B0.7111 (4)0.5795 (3)0.0165 (2)0.0622 (8)
H4B0.70030.56430.07480.075*
C5A0.2392 (4)0.6116 (2)0.22469 (17)0.0449 (6)
H5A0.22580.53510.22320.054*
C5B0.7082 (4)0.4864 (3)0.07061 (18)0.0515 (6)
H5B0.69560.40920.07050.062*
C6A0.2651 (3)0.6286 (2)0.31333 (16)0.0349 (5)
C6B0.7240 (3)0.5078 (2)0.15876 (17)0.0387 (5)
C7A0.2722 (3)0.5341 (2)0.40719 (15)0.0332 (5)
H7A0.33500.54910.45010.040*
C7B0.7119 (3)0.4161 (2)0.25545 (17)0.0362 (5)
H7B0.66190.44690.31050.043*
C8A0.2045 (3)0.42983 (19)0.44251 (15)0.0322 (5)
C8B0.7620 (3)0.2947 (2)0.27668 (17)0.0357 (5)
C9A0.2376 (3)0.3555 (2)0.54369 (16)0.0345 (5)
C9B0.7259 (3)0.2279 (2)0.38432 (18)0.0400 (5)
C10A0.2170 (4)0.1673 (3)0.6645 (2)0.0570 (7)
H10A0.34600.15500.67070.085*
H10B0.18200.09000.67340.085*
H10C0.13990.20510.71430.085*
C10B0.7412 (6)0.0366 (3)0.5018 (2)0.0936 (13)
H10D0.81760.05620.53830.140*
H10E0.77310.04860.50510.140*
H10F0.61160.05540.53030.140*
C11A0.0906 (3)0.3861 (2)0.39206 (17)0.0383 (5)
H11A0.02540.45550.34800.046*
H11B0.00260.34410.44170.046*
C11B0.8615 (3)0.2251 (2)0.20373 (19)0.0462 (6)
H11C0.95730.16180.23320.055*
H11D0.92360.27940.14550.055*
O1A0.2956 (3)0.38962 (15)0.60031 (12)0.0480 (4)
O1B0.6636 (3)0.27411 (17)0.45134 (13)0.0552 (5)
O2A0.1916 (2)0.24515 (15)0.56628 (12)0.0459 (4)
O2B0.7732 (3)0.10769 (17)0.39833 (14)0.0643 (5)
Cl1A0.30217 (12)0.98211 (6)0.22889 (6)0.0646 (2)
Cl1B0.76375 (14)0.86058 (7)0.06837 (6)0.0776 (2)
Br1A0.24789 (4)0.27505 (2)0.314378 (19)0.04929 (9)
Br1B0.69480 (5)0.14955 (3)0.16130 (2)0.06111 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0424 (12)0.0350 (13)0.0363 (12)0.0070 (9)0.0090 (10)0.0092 (10)
C1B0.0519 (14)0.0411 (14)0.0362 (13)0.0080 (11)0.0114 (10)0.0091 (11)
C2A0.0468 (13)0.0323 (13)0.0462 (14)0.0061 (10)0.0112 (11)0.0048 (11)
C2B0.0503 (14)0.0406 (14)0.0472 (15)0.0100 (11)0.0118 (11)0.0034 (12)
C3A0.0648 (17)0.0471 (16)0.0375 (14)0.0092 (13)0.0129 (12)0.0006 (12)
C3B0.0583 (16)0.0582 (18)0.0349 (14)0.0101 (13)0.0069 (11)0.0004 (12)
C4A0.0760 (18)0.0533 (17)0.0336 (13)0.0131 (14)0.0172 (12)0.0079 (12)
C4B0.089 (2)0.064 (2)0.0360 (15)0.0127 (16)0.0175 (14)0.0123 (14)
C5A0.0637 (15)0.0401 (14)0.0341 (13)0.0130 (12)0.0100 (11)0.0104 (11)
C5B0.0742 (18)0.0477 (16)0.0380 (14)0.0128 (13)0.0145 (12)0.0139 (12)
C6A0.0366 (11)0.0365 (13)0.0316 (11)0.0061 (9)0.0060 (9)0.0092 (10)
C6B0.0420 (12)0.0416 (14)0.0335 (12)0.0084 (10)0.0078 (9)0.0097 (10)
C7A0.0395 (11)0.0313 (12)0.0298 (11)0.0065 (9)0.0075 (9)0.0082 (9)
C7B0.0410 (12)0.0378 (13)0.0323 (12)0.0108 (10)0.0070 (9)0.0096 (10)
C8A0.0348 (11)0.0355 (12)0.0285 (11)0.0031 (9)0.0063 (9)0.0133 (10)
C8B0.0356 (11)0.0383 (13)0.0366 (12)0.0089 (9)0.0074 (9)0.0123 (10)
C9A0.0384 (11)0.0318 (12)0.0336 (12)0.0063 (9)0.0038 (9)0.0109 (10)
C9B0.0486 (13)0.0337 (13)0.0403 (13)0.0108 (10)0.0143 (10)0.0064 (11)
C10A0.0814 (19)0.0398 (15)0.0432 (15)0.0159 (14)0.0144 (14)0.0049 (12)
C10B0.176 (4)0.0428 (18)0.0502 (19)0.021 (2)0.019 (2)0.0061 (15)
C11A0.0401 (12)0.0402 (13)0.0383 (12)0.0075 (10)0.0080 (10)0.0145 (10)
C11B0.0472 (13)0.0444 (15)0.0469 (14)0.0084 (11)0.0044 (11)0.0144 (12)
O1A0.0712 (11)0.0431 (10)0.0357 (9)0.0166 (8)0.0183 (8)0.0075 (8)
O1B0.0819 (13)0.0480 (11)0.0358 (9)0.0105 (9)0.0100 (9)0.0121 (8)
O2A0.0687 (11)0.0326 (9)0.0382 (9)0.0164 (8)0.0133 (8)0.0037 (7)
O2B0.1103 (17)0.0354 (11)0.0442 (11)0.0108 (10)0.0138 (10)0.0073 (9)
Cl1A0.0915 (5)0.0330 (4)0.0676 (5)0.0149 (3)0.0219 (4)0.0024 (3)
Cl1B0.1185 (7)0.0414 (4)0.0735 (5)0.0251 (4)0.0339 (5)0.0048 (4)
Br1A0.06512 (17)0.04343 (16)0.04765 (16)0.00739 (12)0.01453 (12)0.02202 (12)
Br1B0.0890 (2)0.05188 (18)0.05424 (18)0.01782 (15)0.01588 (15)0.02436 (14)
Geometric parameters (Å, º) top
C1A—C2A1.373 (3)C7A—H7A0.9300
C1A—C6A1.389 (3)C7B—C8B1.340 (3)
C1A—H1A0.9300C7B—H7B0.9300
C1B—C2B1.375 (3)C8A—C11A1.488 (3)
C1B—C6B1.388 (3)C8A—C9A1.486 (3)
C1B—H1B0.9300C8B—C11B1.480 (3)
C2A—C3A1.376 (3)C8B—C9B1.489 (3)
C2A—Cl1A1.743 (2)C9A—O1A1.202 (3)
C2B—C3B1.376 (4)C9A—O2A1.335 (3)
C2B—Cl1B1.736 (3)C9B—O1B1.194 (3)
C3A—C4A1.375 (4)C9B—O2B1.333 (3)
C3A—H3A0.9300C10A—O2A1.448 (3)
C3B—C4B1.375 (4)C10A—H10A0.9600
C3B—H3B0.9300C10A—H10B0.9600
C4A—C5A1.378 (3)C10A—H10C0.9600
C4A—H4A0.9300C10B—O2B1.452 (4)
C4B—C5B1.380 (4)C10B—H10D0.9600
C4B—H4B0.9300C10B—H10E0.9600
C5A—C6A1.405 (3)C10B—H10F0.9600
C5A—H5A0.9300C11A—Br1A1.971 (2)
C5B—C6B1.395 (3)C11A—H11A0.9700
C5B—H5B0.9300C11A—H11B0.9700
C6A—C7A1.457 (3)C11B—Br1B1.969 (2)
C6B—C7B1.465 (3)C11B—H11C0.9700
C7A—C8A1.335 (3)C11B—H11D0.9700
C2A—C1A—C6A120.3 (2)C8B—C7B—H7B115.1
C2A—C1A—H1A119.9C6B—C7B—H7B115.1
C6A—C1A—H1A119.9C7A—C8A—C11A125.72 (19)
C2B—C1B—C6B120.1 (2)C7A—C8A—C9A116.34 (18)
C2B—C1B—H1B119.9C11A—C8A—C9A117.84 (19)
C6B—C1B—H1B119.9C7B—C8B—C11B125.4 (2)
C1A—C2A—C3A121.8 (2)C7B—C8B—C9B115.7 (2)
C1A—C2A—Cl1A118.87 (18)C11B—C8B—C9B118.7 (2)
C3A—C2A—Cl1A119.3 (2)O1A—C9A—O2A123.0 (2)
C1B—C2B—C3B121.5 (2)O1A—C9A—C8A125.0 (2)
C1B—C2B—Cl1B119.2 (2)O2A—C9A—C8A112.00 (18)
C3B—C2B—Cl1B119.3 (2)O1B—C9B—O2B122.9 (2)
C4A—C3A—C2A118.4 (2)O1B—C9B—C8B125.4 (2)
C4A—C3A—H3A120.8O2B—C9B—C8B111.7 (2)
C2A—C3A—H3A120.8O2A—C10A—H10A109.5
C4B—C3B—C2B118.5 (3)O2A—C10A—H10B109.5
C4B—C3B—H3B120.7H10A—C10A—H10B109.5
C2B—C3B—H3B120.7O2A—C10A—H10C109.5
C3A—C4A—C5A121.1 (2)H10A—C10A—H10C109.5
C3A—C4A—H4A119.5H10B—C10A—H10C109.5
C5A—C4A—H4A119.5O2B—C10B—H10D109.5
C3B—C4B—C5B121.0 (2)O2B—C10B—H10E109.5
C3B—C4B—H4B119.5H10D—C10B—H10E109.5
C5B—C4B—H4B119.5O2B—C10B—H10F109.5
C4A—C5A—C6A120.3 (2)H10D—C10B—H10F109.5
C4A—C5A—H5A119.8H10E—C10B—H10F109.5
C6A—C5A—H5A119.8C8A—C11A—Br1A111.48 (15)
C4B—C5B—C6B120.2 (3)C8A—C11A—H11A109.3
C4B—C5B—H5B119.9Br1A—C11A—H11A109.3
C6B—C5B—H5B119.9C8A—C11A—H11B109.3
C1A—C6A—C5A118.0 (2)Br1A—C11A—H11B109.3
C1A—C6A—C7A116.98 (19)H11A—C11A—H11B108.0
C5A—C6A—C7A125.0 (2)C8B—C11B—Br1B113.16 (16)
C1B—C6B—C5B118.5 (2)C8B—C11B—H11C108.9
C1B—C6B—C7B117.6 (2)Br1B—C11B—H11C108.9
C5B—C6B—C7B123.7 (2)C8B—C11B—H11D108.9
C8A—C7A—C6A131.42 (19)Br1B—C11B—H11D108.9
C8A—C7A—H7A114.3H11C—C11B—H11D107.8
C6A—C7A—H7A114.3C9A—O2A—C10A115.59 (19)
C8B—C7B—C6B129.8 (2)C9B—O2B—C10B114.8 (2)
C6A—C1A—C2A—C3A1.3 (4)C1B—C6B—C7B—C8B153.1 (2)
C6A—C1A—C2A—Cl1A178.57 (18)C5B—C6B—C7B—C8B31.3 (4)
C6B—C1B—C2B—C3B1.7 (4)C6A—C7A—C8A—C11A3.2 (4)
C6B—C1B—C2B—Cl1B179.77 (19)C6A—C7A—C8A—C9A179.4 (2)
C1A—C2A—C3A—C4A0.5 (4)C6B—C7B—C8B—C11B6.4 (4)
Cl1A—C2A—C3A—C4A179.6 (2)C6B—C7B—C8B—C9B178.6 (2)
C1B—C2B—C3B—C4B0.6 (4)C7A—C8A—C9A—O1A11.0 (3)
Cl1B—C2B—C3B—C4B178.7 (2)C11A—C8A—C9A—O1A165.5 (2)
C2A—C3A—C4A—C5A1.6 (4)C7A—C8A—C9A—O2A170.21 (19)
C2B—C3B—C4B—C5B0.3 (4)C11A—C8A—C9A—O2A13.3 (3)
C3A—C4A—C5A—C6A0.8 (4)C7B—C8B—C9B—O1B2.9 (3)
C3B—C4B—C5B—C6B0.1 (5)C11B—C8B—C9B—O1B172.4 (2)
C2A—C1A—C6A—C5A2.0 (3)C7B—C8B—C9B—O2B177.7 (2)
C2A—C1A—C6A—C7A178.6 (2)C11B—C8B—C9B—O2B7.0 (3)
C4A—C5A—C6A—C1A1.0 (4)C7A—C8A—C11A—Br1A95.1 (2)
C4A—C5A—C6A—C7A179.6 (2)C9A—C8A—C11A—Br1A88.7 (2)
C2B—C1B—C6B—C5B1.9 (4)C7B—C8B—C11B—Br1B101.0 (2)
C2B—C1B—C6B—C7B177.7 (2)C9B—C8B—C11B—Br1B84.2 (2)
C4B—C5B—C6B—C1B1.0 (4)O1A—C9A—O2A—C10A0.3 (3)
C4B—C5B—C6B—C7B176.5 (2)C8A—C9A—O2A—C10A179.1 (2)
C1A—C6A—C7A—C8A157.6 (2)O1B—C9B—O2B—C10B0.7 (4)
C5A—C6A—C7A—C8A23.1 (4)C8B—C9B—O2B—C10B179.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1A—H1A···O1Bi0.932.533.429 (3)161
C1B—H1B···O1Ai0.932.513.380 (3)156
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC11H10BrClO2
Mr289.54
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)7.4523 (3), 11.7003 (4), 14.3121 (5)
α, β, γ (°)72.078 (2), 76.539 (2), 76.773 (2)
V3)1137.98 (7)
Z4
Radiation typeMo Kα
µ (mm1)3.82
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2008)
Tmin, Tmax0.330, 0.466
No. of measured, independent and
observed [I > 2σ(I)] reflections
27124, 6597, 4205
Rint0.032
(sin θ/λ)max1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.092, 1.00
No. of reflections6597
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.85, 0.49

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1A—H1A···O1Bi0.932.533.429 (3)161
C1B—H1B···O1Ai0.932.513.380 (3)156
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

The authors thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT, Chennai, India, for the data collection. KS thanks the University Grant Commission (UGC), India, for Minor Research Project support.

References

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First citationSwaminathan, K., Sethusankar, K., Devaraj, A. & Bakthadoss, M. (2013). Acta Cryst. E69, o572.  CSD CrossRef IUCr Journals

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