organic compounds
2,6-Dibromo-4-formylphenyl 3-phenylprop-2-enoate
aAsthagiri Herbal Research Foundation, Perungudi, Chennai 600 096, India, and bDepartment of Physics, Presidency College, Chennai 600 005, India
*Correspondence e-mail: aravindhanpresidency@gmail.com
Molecules of the title compound, C16H10Br2O3, adopt an E conformation about the C=C double bond. The dihedral angle between the two aromatic rings is 78.0 (7)°. In the crystal, molecules are linked through weak C—H⋯O hydrogen bonds.
Related literature
For the biological activity of cinnamoyl derivatives, see: De et al. (2011); Obioran et al. (1986); Cremlyn et al. (1984).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812037427/bt6828sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037427/bt6828Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812037427/bt6828Isup3.cml
To a solution of 3,5-dibromo benzaldehyde (0.03 mol) in chloroform (100 ml) cinnamoyl chloride (0.03 mol) was added followed by addition of triethyl amine (0.03 mol). Then the reaction was stirred at room temperature for 3 h. The reaction mixture was quenched with water and the chloroform layer was separated. The combined chloroform layers were washed with 5% NaOH solution followed by water wash and dried with sodium sulfate. Then the mixture was concentrated under reduced pressure. The obtained solid was crystallized in a mixture of methanol:chloroform.
H atoms were refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.93 Å.
Cinnamoyl derivatives exhibit a variety of pharmacological properties, e.g anticancer, antitumor and antimicrobial activities (De et al., 2011; Obioran et al., 1986; Cremlyn et al., 1984). In view of their importance, the ═C double bond is E. The dihedral angle between the two aromatic rings is 78.0 (7)°. In the crystal packing, molecules are linked through weak C—H···O hydrogen bonds (Fig. 2).
determination of the title compound was carried out and the results are presented herein. The molecular structure of the title compound is shown in Fig. 1. In the molecule, the configuration about the CFor the biological activity of cinnamoyl derivatives, see: De et al. (2011); Obioran et al. (1986); Cremlyn et al. (1984).
Data collection: APEX2 (Bruker, 2004); cell
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 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).C16H10Br2O3 | Z = 2 |
Mr = 410.06 | F(000) = 400 |
Triclinic, P1 | Dx = 1.753 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0846 (3) Å | Cell parameters from 8834 reflections |
b = 9.0149 (4) Å | θ = 2.1–31.2° |
c = 11.8995 (5) Å | µ = 5.22 mm−1 |
α = 77.429 (2)° | T = 293 K |
β = 73.918 (2)° | Block, colourless |
γ = 70.236 (2)° | 0.25 × 0.20 × 0.20 mm |
V = 776.83 (6) Å3 |
Bruker Kappa APEXII CCD diffractometer | 3764 independent reflections |
Radiation source: fine-focus sealed tube | 2282 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω and φ scan | θmax = 28.2°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker 2004) | h = −10→10 |
Tmin = 0.979, Tmax = 0.983 | k = −11→11 |
15811 measured reflections | l = −15→15 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.7467P] where P = (Fo2 + 2Fc2)/3 |
3764 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
C16H10Br2O3 | γ = 70.236 (2)° |
Mr = 410.06 | V = 776.83 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.0846 (3) Å | Mo Kα radiation |
b = 9.0149 (4) Å | µ = 5.22 mm−1 |
c = 11.8995 (5) Å | T = 293 K |
α = 77.429 (2)° | 0.25 × 0.20 × 0.20 mm |
β = 73.918 (2)° |
Bruker Kappa APEXII CCD diffractometer | 3764 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker 2004) | 2282 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.983 | Rint = 0.029 |
15811 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.63 e Å−3 |
3764 reflections | Δρmin = −0.52 e Å−3 |
190 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O2 | 0.5056 (3) | 0.8407 (3) | 0.3049 (2) | 0.0643 (7) | |
Br2 | 0.28505 (7) | 0.69030 (5) | 0.52006 (4) | 0.07858 (18) | |
Br1 | 0.54158 (7) | 1.17400 (6) | 0.21211 (4) | 0.08435 (18) | |
C10 | 0.3929 (4) | 0.9517 (4) | 0.3796 (3) | 0.0499 (8) | |
C15 | 0.3931 (5) | 1.1088 (4) | 0.3529 (3) | 0.0555 (9) | |
C12 | 0.1796 (5) | 1.0109 (4) | 0.5601 (3) | 0.0562 (9) | |
H12 | 0.1060 | 0.9786 | 0.6297 | 0.067* | |
C1 | 0.8079 (5) | 0.4509 (4) | 0.1110 (4) | 0.0612 (10) | |
C16 | 0.0729 (6) | 1.2807 (6) | 0.6205 (4) | 0.0745 (12) | |
H16 | −0.0078 | 1.2465 | 0.6849 | 0.089* | |
C13 | 0.1840 (5) | 1.1664 (4) | 0.5332 (3) | 0.0559 (9) | |
C5 | 1.0667 (7) | 0.2245 (5) | 0.1043 (5) | 0.0881 (14) | |
H5 | 1.1658 | 0.1610 | 0.1351 | 0.106* | |
O3 | 0.0815 (5) | 1.4077 (4) | 0.6125 (3) | 0.0920 (10) | |
C11 | 0.2853 (5) | 0.9037 (4) | 0.4828 (3) | 0.0517 (8) | |
C2 | 0.7771 (6) | 0.4158 (6) | 0.0153 (4) | 0.0796 (13) | |
H2 | 0.6803 | 0.4821 | −0.0168 | 0.096* | |
C9 | 0.4246 (7) | 0.8097 (5) | 0.2269 (4) | 0.0657 (11) | |
C7 | 0.6899 (6) | 0.5893 (5) | 0.1768 (4) | 0.0704 (11) | |
H7 | 0.7306 | 0.6079 | 0.2368 | 0.085* | |
C14 | 0.2892 (5) | 1.2157 (4) | 0.4296 (3) | 0.0573 (9) | |
H14 | 0.2901 | 1.3212 | 0.4114 | 0.069* | |
C8 | 0.5420 (7) | 0.6811 (6) | 0.1574 (4) | 0.0830 (13) | |
H8 | 0.5037 | 0.6671 | 0.0946 | 0.100* | |
C6 | 0.9537 (6) | 0.3553 (5) | 0.1536 (4) | 0.0721 (11) | |
H6 | 0.9770 | 0.3801 | 0.2184 | 0.087* | |
O1 | 0.2767 (5) | 0.8782 (4) | 0.2205 (3) | 0.0886 (9) | |
C4 | 1.0338 (8) | 0.1871 (6) | 0.0099 (6) | 0.0954 (18) | |
H4 | 1.1101 | 0.0970 | −0.0237 | 0.114* | |
C3 | 0.8902 (8) | 0.2802 (7) | −0.0361 (5) | 0.0943 (17) | |
H3 | 0.8673 | 0.2543 | −0.1006 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O2 | 0.0470 (14) | 0.0607 (15) | 0.0710 (17) | −0.0052 (12) | −0.0006 (13) | −0.0138 (13) |
Br2 | 0.1027 (4) | 0.0525 (2) | 0.0777 (3) | −0.0311 (2) | −0.0149 (2) | 0.00322 (19) |
Br1 | 0.0860 (3) | 0.0953 (3) | 0.0707 (3) | −0.0500 (3) | −0.0005 (2) | 0.0062 (2) |
C10 | 0.0397 (19) | 0.0526 (19) | 0.056 (2) | −0.0126 (15) | −0.0095 (16) | −0.0082 (17) |
C15 | 0.050 (2) | 0.063 (2) | 0.056 (2) | −0.0249 (17) | −0.0117 (17) | −0.0009 (18) |
C12 | 0.053 (2) | 0.066 (2) | 0.051 (2) | −0.0247 (18) | −0.0061 (17) | −0.0090 (18) |
C1 | 0.064 (3) | 0.052 (2) | 0.062 (2) | −0.0278 (19) | 0.0140 (19) | −0.0159 (18) |
C16 | 0.072 (3) | 0.090 (3) | 0.074 (3) | −0.031 (2) | −0.016 (2) | −0.025 (2) |
C13 | 0.052 (2) | 0.059 (2) | 0.063 (2) | −0.0162 (17) | −0.0154 (18) | −0.0196 (18) |
C5 | 0.077 (3) | 0.055 (2) | 0.121 (4) | −0.017 (2) | −0.003 (3) | −0.016 (3) |
O3 | 0.110 (3) | 0.076 (2) | 0.098 (2) | −0.0113 (19) | −0.037 (2) | −0.0376 (19) |
C11 | 0.051 (2) | 0.0473 (18) | 0.060 (2) | −0.0200 (16) | −0.0151 (17) | −0.0012 (16) |
C2 | 0.067 (3) | 0.084 (3) | 0.086 (3) | −0.033 (2) | 0.005 (2) | −0.018 (3) |
C9 | 0.079 (3) | 0.057 (2) | 0.060 (2) | −0.020 (2) | −0.002 (2) | −0.0219 (19) |
C7 | 0.064 (3) | 0.073 (3) | 0.073 (3) | −0.034 (2) | −0.007 (2) | 0.006 (2) |
C14 | 0.061 (2) | 0.052 (2) | 0.067 (2) | −0.0254 (18) | −0.0200 (19) | −0.0054 (18) |
C8 | 0.085 (3) | 0.089 (3) | 0.084 (3) | −0.029 (3) | −0.025 (3) | −0.017 (3) |
C6 | 0.071 (3) | 0.058 (2) | 0.080 (3) | −0.022 (2) | −0.001 (2) | −0.009 (2) |
O1 | 0.090 (2) | 0.087 (2) | 0.092 (2) | −0.0086 (19) | −0.0341 (19) | −0.0304 (18) |
C4 | 0.083 (4) | 0.067 (3) | 0.131 (5) | −0.037 (3) | 0.029 (3) | −0.047 (3) |
C3 | 0.102 (4) | 0.118 (4) | 0.085 (3) | −0.069 (4) | 0.015 (3) | −0.045 (3) |
O2—C9 | 1.393 (5) | C13—C14 | 1.370 (5) |
O2—C10 | 1.394 (4) | C5—C4 | 1.355 (8) |
Br2—C11 | 1.878 (3) | C5—C6 | 1.358 (6) |
Br1—C15 | 1.878 (4) | C5—H5 | 0.9300 |
C10—C11 | 1.373 (5) | C2—C3 | 1.401 (7) |
C10—C15 | 1.383 (5) | C2—H2 | 0.9300 |
C15—C14 | 1.371 (5) | C9—O1 | 1.161 (5) |
C12—C13 | 1.379 (5) | C9—C8 | 1.473 (6) |
C12—C11 | 1.379 (5) | C7—C8 | 1.252 (6) |
C12—H12 | 0.9300 | C7—H7 | 0.9300 |
C1—C2 | 1.352 (6) | C14—H14 | 0.9300 |
C1—C6 | 1.357 (6) | C8—H8 | 0.9300 |
C1—C7 | 1.512 (6) | C6—H6 | 0.9300 |
C16—O3 | 1.152 (5) | C4—C3 | 1.358 (8) |
C16—C13 | 1.507 (6) | C4—H4 | 0.9300 |
C16—H16 | 0.9300 | C3—H3 | 0.9300 |
C9—O2—C10 | 115.2 (3) | C1—C2—C3 | 120.4 (5) |
C11—C10—C15 | 119.6 (3) | C1—C2—H2 | 119.8 |
C11—C10—O2 | 119.8 (3) | C3—C2—H2 | 119.8 |
C15—C10—O2 | 120.6 (3) | O1—C9—O2 | 122.1 (3) |
C14—C15—C10 | 120.5 (3) | O1—C9—C8 | 124.1 (4) |
C14—C15—Br1 | 120.0 (3) | O2—C9—C8 | 113.8 (4) |
C10—C15—Br1 | 119.5 (3) | C8—C7—C1 | 125.6 (5) |
C13—C12—C11 | 119.5 (3) | C8—C7—H7 | 117.2 |
C13—C12—H12 | 120.3 | C1—C7—H7 | 117.2 |
C11—C12—H12 | 120.3 | C15—C14—C13 | 119.6 (3) |
C2—C1—C6 | 118.6 (4) | C15—C14—H14 | 120.2 |
C2—C1—C7 | 124.8 (4) | C13—C14—H14 | 120.2 |
C6—C1—C7 | 116.5 (4) | C7—C8—C9 | 124.6 (5) |
O3—C16—C13 | 124.2 (5) | C7—C8—H8 | 117.7 |
O3—C16—H16 | 117.9 | C9—C8—H8 | 117.7 |
C13—C16—H16 | 117.9 | C1—C6—C5 | 122.0 (5) |
C14—C13—C12 | 120.6 (3) | C1—C6—H6 | 119.0 |
C14—C13—C16 | 120.5 (4) | C5—C6—H6 | 119.0 |
C12—C13—C16 | 118.8 (4) | C3—C4—C5 | 120.5 (5) |
C4—C5—C6 | 119.5 (5) | C3—C4—H4 | 119.8 |
C4—C5—H5 | 120.3 | C5—C4—H4 | 119.8 |
C6—C5—H5 | 120.3 | C4—C3—C2 | 119.0 (5) |
C10—C11—C12 | 120.3 (3) | C4—C3—H3 | 120.5 |
C10—C11—Br2 | 119.8 (3) | C2—C3—H3 | 120.5 |
C12—C11—Br2 | 119.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.48 | 3.221 (6) | 136 |
C7—H7···O2 | 0.93 | 2.39 | 2.764 (3) | 104 |
Symmetry code: (i) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C16H10Br2O3 |
Mr | 410.06 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.0846 (3), 9.0149 (4), 11.8995 (5) |
α, β, γ (°) | 77.429 (2), 73.918 (2), 70.236 (2) |
V (Å3) | 776.83 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 5.22 |
Crystal size (mm) | 0.25 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Bruker 2004) |
Tmin, Tmax | 0.979, 0.983 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15811, 3764, 2282 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.665 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.107, 0.98 |
No. of reflections | 3764 |
No. of parameters | 190 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.52 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.93 | 2.48 | 3.221 (6) | 136 |
Symmetry code: (i) x+1, y−1, z. |
Acknowledgements
SA thanks the UGC, India, for financial support.
References
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremlyn, R. J., Thandi, K. & Wilson, R. (1984). Indian J. Chem. Sect. B, 23, 94–96. Google Scholar
De, P., Baltas, M. & Bedos-Belval, F. (2011). Curr. Med. Chem. 18, 1672–1703. CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Cinnamoyl derivatives exhibit a variety of pharmacological properties, e.g anticancer, antitumor and antimicrobial activities (De et al., 2011; Obioran et al., 1986; Cremlyn et al., 1984). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented herein. The molecular structure of the title compound is shown in Fig. 1. In the molecule, the configuration about the C═C double bond is E. The dihedral angle between the two aromatic rings is 78.0 (7)°. In the crystal packing, molecules are linked through weak C—H···O hydrogen bonds (Fig. 2).