2,6-Dibromo-4-formyl­phenyl 3-phenyl­prop-2-enoate

Suresh Kumar, C.; Jagadeesan, G.; Dhamodaran, S.; Ananth, K.; Aravindhan, S.

doi:10.1107/S1600536812037427

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2873

https://doi.org/10.1107/S1600536812037427

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2,6-Dibromo-4-formylphenyl 3-phenylprop-2-enoate

C. Suresh Kumar,^a G. Jagadeesan,^b S. Dhamodaran,^a Karthik Ananth ^a and S. Aravindhan ^b ^*

^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

(Received 24 August 2012; accepted 30 August 2012; online 8 September 2012)

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

C₁₆H₁₀Br₂O₃
M_r = 410.06
Triclinic, $[P \overline 1]$
a = 8.0846 (3) Å
b = 9.0149 (4) Å
c = 11.8995 (5) Å
α = 77.429 (2)°
β = 73.918 (2)°
γ = 70.236 (2)°
V = 776.83 (6) Å³
Z = 2
Mo Kα radiation
μ = 5.22 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2004 ) T_min = 0.979, T_max = 0.983
15811 measured reflections
3764 independent reflections
2282 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.107
S = 0.98
3764 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

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 for Windows (Farrugia, 1997 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812037427/bt6828sup1.cif

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

checkCIF report

Comment top

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).

Related literature top

For the biological activity of cinnamoyl derivatives, see: De et al. (2011); Obioran et al. (1986); Cremlyn et al. (1984).

Experimental top

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.

Structure description top

For the biological activity of cinnamoyl derivatives, see: De et al. (2011); Obioran et al. (1986); Cremlyn et al. (1984).

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 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids. H atoms are omitted for clarity.
	Fig. 2. Crystal packing diagram. H atoms not involved in intermolecular hydrogen bonding (dashed lines) have been omitted for clarity.

2,6-Dibromo-4-formylphenyl 3-phenylprop-2-enoate top

Crystal data top

C₁₆H₁₀Br₂O₃	Z = 2
M_r = 410.06	F(000) = 400
Triclinic, P1	D_x = 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	3764 independent reflections
Radiation source: fine-focus sealed tube	2282 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ω and φ scan	θ_max = 28.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −10→10
T_min = 0.979, T_max = 0.983	k = −11→11
15811 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0417P)² + 0.7467P] where P = (F_o² + 2F_c²)/3
3764 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

C₁₆H₁₀Br₂O₃	γ = 70.236 (2)°
M_r = 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)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3764 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	2282 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.029
15811 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 0.98	Δρ_max = 0.63 e Å⁻³
3764 reflections	Δρ_min = −0.52 e Å⁻³
190 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	15811, 3764, 2282
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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