2,6-Dibromo-4-formyl-phenyl 3-phenyl-prop-2-enoate.

Mol-ecules of the title compound, C(16)H(10)Br(2)O(3), 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, mol-ecules 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 = 410.06

Triclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.107

S = 0.98

3764 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.52 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037427/bt6828sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037427/bt6828Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037427/bt6828Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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

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) .