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

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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.041
• wR factor = 0.107
• Data-to-parameter ratio = 19.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C1     --  C7      ..       10.5 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C8     --  C9      ..       10.0 su

Alert level C
PLAT331_ALERT_2_C Small Average Phenyl   C-C Dist. C1     -C6            1.36 Ang.
PLAT341_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0064 Ang
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          9

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         48

   0 ALERT level A = Most likely a serious problem - resolve or explain
   2 ALERT level B = A potentially serious problem, consider carefully
   4 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

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

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

S2. Experimental

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.

S3. Refinement

H atoms were refined with fixed individual displacement parameters [U(H) = 1.2 U_eq(C)] using a riding model with C—H = 0.93 Å.

Computing details

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

	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

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.107	H-atom parameters constrained
S = 0.98	w = 1/[σ^2(Fo^2) + (0.0417P)^2 + 0.7467P] where P = (Fo^2 + 2Fc^2)/3
3764 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.63 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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 (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1^i	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.