organic compounds
(2E)-3-(2-Bromophenyl)-1-(5-bromothiophen-2-yl)prop-2-en-1-one
aInstitute of Pharmacy, GITAM University, Visakhapatnam-45, Andhrapradesh, India, bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, cKaruna College of Pharmacy, Thirumittacode, Palakad 679 533, Kerala, India, and dCollege of Pharmacy, Andhra University, Visakhapatnam, Andhrapradesh, India
*Correspondence e-mail: devarajegowda@yahoo.com
The 13H8Br2OS, contains two molecules, in which the dihedral angles between the thiophene and benzene rings are 10.5 (3) and 33.2 (4)°. There are no significant directional interactions in the crystal.
of the title compound, CRelated literature
For further details of conformational modelling, see: Pascard (1995); Thomas et al. (2004). For related structures, see: Liang et al. (2011); Alex et al. (1993); Li & Su (1993).
Experimental
Crystal data
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).
Supporting information
10.1107/S1600536812047939/hb6986sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812047939/hb6986Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812047939/hb6986Isup3.cml
A mixture of 2-acetyl-5-bromothiophene (0.01 mole) and 2-bromobenzaldehyde (0.01 mole) were stirred in ethanol (30 ml) and then an aqueous solution of potassium hydroxide (40%, 15 ml)was added to it. The mixture was kept over night at room temperature and then it was poured into crushed ice and acidified with dilute hydrochloric acid. The precipiteted chalcone was filtered and crystallized from ethanol as colourless prisms.
All H atoms were positioned at calculated positions C—H = 0.93 Å for aromatic H and refined using a riding model with Uiso(H) = 1.2Ueq(C)for aromatic H. Attempts to model non-merohedral
resulted in no improvement.Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Packing of the molecules. |
C13H8Br2OS | F(000) = 1440 |
Mr = 372.07 | Dx = 1.908 Mg m−3 |
Monoclinic, Cc | Melting point: 403 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 34.524 (8) Å | Cell parameters from 5988 reflections |
b = 3.9994 (9) Å | θ = 1.8–28.0° |
c = 23.428 (5) Å | µ = 6.40 mm−1 |
β = 126.804 (3)° | T = 293 K |
V = 2590.1 (10) Å3 | Prism, colourless |
Z = 8 | 0.22 × 0.15 × 0.12 mm |
Oxford Diffraction Xcalibur diffractometer | 5988 independent reflections |
Radiation source: Mova (Mo) X-ray Source | 4266 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.051 |
Detector resolution: 16.0839 pixels mm-1 | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −44→44 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −5→5 |
Tmin = 0.228, Tmax = 1.000 | l = −30→30 |
13574 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0425P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.97 | (Δ/σ)max < 0.001 |
5988 reflections | Δρmax = 0.58 e Å−3 |
308 parameters | Δρmin = −0.44 e Å−3 |
2 restraints | Absolute structure: Flack (1983), 2846 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.000 (13) |
C13H8Br2OS | V = 2590.1 (10) Å3 |
Mr = 372.07 | Z = 8 |
Monoclinic, Cc | Mo Kα radiation |
a = 34.524 (8) Å | µ = 6.40 mm−1 |
b = 3.9994 (9) Å | T = 293 K |
c = 23.428 (5) Å | 0.22 × 0.15 × 0.12 mm |
β = 126.804 (3)° |
Oxford Diffraction Xcalibur diffractometer | 5988 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 4266 reflections with I > 2σ(I) |
Tmin = 0.228, Tmax = 1.000 | Rint = 0.051 |
13574 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.109 | Δρmax = 0.58 e Å−3 |
S = 0.97 | Δρmin = −0.44 e Å−3 |
5988 reflections | Absolute structure: Flack (1983), 2846 Friedel pairs |
308 parameters | Absolute structure parameter: 0.000 (13) |
2 restraints |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 | ||
Br1A | 0.49316 (2) | 0.58296 (18) | 0.54216 (3) | 0.05287 (19) | |
Br2A | 0.83387 (2) | −0.64813 (18) | 0.74346 (3) | 0.0554 (2) | |
S3A | 0.58670 (6) | 0.2854 (4) | 0.57198 (9) | 0.0491 (4) | |
O4A | 0.6766 (2) | −0.0276 (16) | 0.6126 (3) | 0.0756 (17) | |
C5A | 0.5553 (2) | 0.3956 (14) | 0.6035 (4) | 0.0416 (14) | |
C6A | 0.5789 (2) | 0.3287 (16) | 0.6733 (3) | 0.0468 (16) | |
H6A | 0.5664 | 0.3709 | 0.6983 | 0.056* | |
C7A | 0.6247 (3) | 0.1873 (16) | 0.7037 (4) | 0.0498 (17) | |
H7A | 0.6463 | 0.1295 | 0.7516 | 0.060* | |
C8A | 0.6338 (2) | 0.1449 (14) | 0.6553 (3) | 0.0391 (14) | |
C9A | 0.6763 (3) | 0.0017 (17) | 0.6631 (4) | 0.0466 (15) | |
C10A | 0.7161 (3) | −0.1089 (17) | 0.7347 (4) | 0.0531 (18) | |
H10A | 0.7143 | −0.0709 | 0.7722 | 0.064* | |
C11A | 0.7544 (2) | −0.2607 (15) | 0.7476 (4) | 0.0445 (15) | |
H11A | 0.7537 | −0.3056 | 0.7081 | 0.053* | |
C12A | 0.7978 (2) | −0.3670 (14) | 0.8162 (4) | 0.0404 (14) | |
C13A | 0.8033 (3) | −0.3032 (18) | 0.8802 (4) | 0.0549 (18) | |
H13A | 0.7785 | −0.1964 | 0.8779 | 0.066* | |
C14A | 0.8448 (3) | −0.3956 (19) | 0.9463 (4) | 0.0544 (18) | |
H14A | 0.8472 | −0.3529 | 0.9873 | 0.065* | |
C15A | 0.8820 (3) | −0.5488 (17) | 0.9512 (4) | 0.0535 (17) | |
H15A | 0.9097 | −0.6088 | 0.9957 | 0.064* | |
C16A | 0.8787 (3) | −0.6158 (15) | 0.8903 (4) | 0.0495 (16) | |
H16A | 0.9043 | −0.7155 | 0.8934 | 0.059* | |
C17A | 0.8364 (2) | −0.5300 (14) | 0.8248 (3) | 0.0405 (14) | |
Br1B | 0.84144 (3) | −1.0016 (2) | 1.09708 (4) | 0.0628 (2) | |
Br2B | 0.47871 (3) | −0.1788 (2) | 0.68156 (4) | 0.0673 (2) | |
S3B | 0.75065 (6) | −0.6749 (4) | 0.96145 (9) | 0.0487 (4) | |
O4B | 0.6618 (2) | −0.3491 (14) | 0.8424 (3) | 0.0657 (14) | |
C5B | 0.7785 (2) | −0.8334 (15) | 1.0463 (3) | 0.0461 (16) | |
C6B | 0.7510 (3) | −0.8115 (17) | 1.0687 (4) | 0.0541 (17) | |
H6B | 0.7601 | −0.8887 | 1.1126 | 0.065* | |
C7B | 0.7066 (2) | −0.6571 (17) | 1.0175 (3) | 0.0492 (16) | |
H7B | 0.6832 | −0.6189 | 1.0248 | 0.059* | |
C8B | 0.7003 (2) | −0.5683 (15) | 0.9569 (3) | 0.0418 (15) | |
C9B | 0.6608 (3) | −0.4037 (18) | 0.8926 (4) | 0.0468 (14) | |
C10B | 0.6193 (2) | −0.2910 (17) | 0.8921 (3) | 0.0478 (16) | |
H10B | 0.6217 | −0.3147 | 0.9336 | 0.057* | |
C11B | 0.5802 (3) | −0.1621 (17) | 0.8367 (4) | 0.0484 (16) | |
H11B | 0.5789 | −0.1439 | 0.7959 | 0.058* | |
C12B | 0.5375 (2) | −0.0406 (16) | 0.8307 (3) | 0.0421 (15) | |
C13B | 0.5440 (3) | 0.0730 (18) | 0.8926 (4) | 0.0573 (18) | |
H13B | 0.5748 | 0.0715 | 0.9357 | 0.069* | |
C14B | 0.5053 (3) | 0.187 (2) | 0.8903 (4) | 0.066 (2) | |
H14B | 0.5102 | 0.2568 | 0.9320 | 0.080* | |
C15B | 0.4599 (3) | 0.198 (2) | 0.8271 (5) | 0.064 (2) | |
H15B | 0.4339 | 0.2748 | 0.8258 | 0.077* | |
C16B | 0.4530 (3) | 0.0956 (18) | 0.7660 (4) | 0.0573 (19) | |
H16B | 0.4223 | 0.1065 | 0.7227 | 0.069* | |
C17B | 0.4913 (3) | −0.0237 (16) | 0.7683 (4) | 0.0484 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1A | 0.0393 (4) | 0.0547 (3) | 0.0606 (5) | 0.0062 (3) | 0.0277 (4) | 0.0033 (4) |
Br2A | 0.0560 (5) | 0.0566 (4) | 0.0650 (5) | 0.0045 (3) | 0.0424 (4) | −0.0061 (4) |
S3A | 0.0474 (10) | 0.0591 (10) | 0.0469 (9) | 0.0091 (8) | 0.0315 (9) | 0.0035 (8) |
O4A | 0.060 (4) | 0.114 (5) | 0.066 (4) | 0.028 (3) | 0.045 (3) | 0.009 (3) |
C5A | 0.035 (3) | 0.034 (3) | 0.055 (4) | −0.004 (3) | 0.026 (3) | −0.005 (3) |
C6A | 0.047 (4) | 0.057 (4) | 0.043 (4) | 0.009 (3) | 0.031 (3) | 0.004 (3) |
C7A | 0.049 (4) | 0.052 (4) | 0.048 (4) | 0.010 (3) | 0.029 (4) | 0.004 (3) |
C8A | 0.042 (4) | 0.034 (3) | 0.048 (4) | 0.003 (3) | 0.030 (3) | 0.002 (3) |
C9A | 0.046 (4) | 0.052 (4) | 0.051 (4) | 0.002 (3) | 0.034 (4) | 0.000 (3) |
C10A | 0.054 (5) | 0.053 (4) | 0.069 (5) | 0.006 (3) | 0.045 (4) | 0.003 (4) |
C11A | 0.037 (4) | 0.049 (3) | 0.054 (4) | 0.001 (3) | 0.030 (3) | 0.004 (3) |
C12A | 0.035 (3) | 0.037 (3) | 0.051 (4) | 0.000 (3) | 0.027 (3) | 0.004 (3) |
C13A | 0.054 (5) | 0.058 (4) | 0.074 (5) | 0.004 (4) | 0.050 (4) | 0.000 (4) |
C14A | 0.053 (5) | 0.062 (4) | 0.045 (4) | −0.007 (4) | 0.028 (4) | −0.003 (3) |
C15A | 0.046 (4) | 0.055 (4) | 0.056 (4) | −0.001 (3) | 0.029 (4) | 0.000 (3) |
C16A | 0.040 (4) | 0.044 (4) | 0.061 (4) | 0.000 (3) | 0.028 (4) | −0.001 (3) |
C17A | 0.048 (4) | 0.031 (3) | 0.050 (4) | −0.002 (3) | 0.033 (4) | 0.000 (3) |
Br1B | 0.0518 (5) | 0.0594 (4) | 0.0590 (5) | 0.0080 (4) | 0.0235 (4) | −0.0050 (4) |
Br2B | 0.0649 (6) | 0.0759 (5) | 0.0509 (4) | 0.0063 (4) | 0.0293 (4) | −0.0050 (4) |
S3B | 0.0485 (10) | 0.0561 (10) | 0.0487 (9) | −0.0001 (8) | 0.0330 (9) | 0.0004 (8) |
O4B | 0.064 (4) | 0.090 (4) | 0.050 (3) | 0.016 (3) | 0.037 (3) | 0.014 (3) |
C5B | 0.049 (4) | 0.034 (3) | 0.048 (4) | −0.005 (3) | 0.025 (4) | −0.004 (3) |
C6B | 0.057 (5) | 0.058 (4) | 0.049 (4) | 0.004 (4) | 0.033 (4) | 0.008 (3) |
C7B | 0.042 (4) | 0.064 (4) | 0.048 (4) | −0.003 (3) | 0.030 (4) | −0.002 (3) |
C8B | 0.050 (4) | 0.039 (3) | 0.043 (4) | −0.003 (3) | 0.032 (3) | −0.003 (3) |
C9B | 0.045 (4) | 0.049 (3) | 0.042 (3) | −0.001 (3) | 0.024 (3) | 0.000 (3) |
C10B | 0.040 (4) | 0.060 (4) | 0.037 (3) | 0.000 (3) | 0.019 (3) | 0.005 (3) |
C11B | 0.050 (4) | 0.056 (4) | 0.045 (4) | −0.002 (3) | 0.032 (4) | 0.000 (3) |
C12B | 0.035 (4) | 0.044 (4) | 0.040 (3) | −0.001 (3) | 0.019 (3) | 0.006 (3) |
C13B | 0.058 (5) | 0.061 (4) | 0.062 (5) | −0.010 (4) | 0.041 (4) | −0.003 (4) |
C14B | 0.072 (6) | 0.077 (6) | 0.056 (5) | 0.008 (5) | 0.042 (5) | −0.009 (4) |
C15B | 0.059 (5) | 0.068 (5) | 0.076 (6) | 0.003 (4) | 0.046 (5) | −0.004 (4) |
C16B | 0.046 (5) | 0.061 (5) | 0.056 (4) | 0.008 (3) | 0.026 (4) | 0.011 (4) |
C17B | 0.059 (5) | 0.043 (4) | 0.055 (4) | 0.005 (3) | 0.040 (4) | 0.007 (3) |
Br1A—C5A | 1.880 (6) | Br1B—C5B | 1.870 (7) |
Br2A—C17A | 1.913 (6) | Br2B—C17B | 1.909 (7) |
S3A—C5A | 1.694 (6) | S3B—C5B | 1.729 (7) |
S3A—C8A | 1.723 (7) | S3B—C8B | 1.731 (7) |
O4A—C9A | 1.197 (8) | O4B—C9B | 1.217 (9) |
C5A—C6A | 1.346 (9) | C5B—C6B | 1.333 (10) |
C6A—C7A | 1.407 (9) | C6B—C7B | 1.403 (10) |
C6A—H6A | 0.9300 | C6B—H6B | 0.9300 |
C7A—C8A | 1.354 (9) | C7B—C8B | 1.350 (9) |
C7A—H7A | 0.9300 | C7B—H7B | 0.9300 |
C8A—C9A | 1.481 (9) | C8B—C9B | 1.449 (10) |
C9A—C10A | 1.461 (10) | C9B—C10B | 1.496 (11) |
C10A—C11A | 1.316 (9) | C10B—C11B | 1.293 (9) |
C10A—H10A | 0.9300 | C10B—H10B | 0.9300 |
C11A—C12A | 1.458 (9) | C11B—C12B | 1.478 (10) |
C11A—H11A | 0.9300 | C11B—H11B | 0.9300 |
C12A—C17A | 1.385 (9) | C12B—C17B | 1.376 (9) |
C12A—C13A | 1.416 (10) | C12B—C13B | 1.402 (10) |
C13A—C14A | 1.388 (11) | C13B—C14B | 1.382 (11) |
C13A—H13A | 0.9300 | C13B—H13B | 0.9300 |
C14A—C15A | 1.364 (10) | C14B—C15B | 1.368 (11) |
C14A—H14A | 0.9300 | C14B—H14B | 0.9300 |
C15A—C16A | 1.388 (10) | C15B—C16B | 1.367 (10) |
C15A—H15A | 0.9300 | C15B—H15B | 0.9300 |
C16A—C17A | 1.387 (9) | C16B—C17B | 1.376 (10) |
C16A—H16A | 0.9300 | C16B—H16B | 0.9300 |
C5A—S3A—C8A | 90.4 (3) | C5B—S3B—C8B | 90.4 (3) |
C6A—C5A—S3A | 113.4 (5) | C6B—C5B—S3B | 113.1 (5) |
C6A—C5A—Br1A | 126.2 (5) | C6B—C5B—Br1B | 127.1 (5) |
S3A—C5A—Br1A | 120.4 (4) | S3B—C5B—Br1B | 119.8 (4) |
C5A—C6A—C7A | 112.0 (6) | C5B—C6B—C7B | 111.4 (6) |
C5A—C6A—H6A | 124.0 | C5B—C6B—H6B | 124.3 |
C7A—C6A—H6A | 124.0 | C7B—C6B—H6B | 124.3 |
C8A—C7A—C6A | 112.2 (6) | C8B—C7B—C6B | 114.8 (6) |
C8A—C7A—H7A | 123.9 | C8B—C7B—H7B | 122.6 |
C6A—C7A—H7A | 123.9 | C6B—C7B—H7B | 122.6 |
C7A—C8A—C9A | 130.8 (6) | C7B—C8B—C9B | 132.2 (7) |
C7A—C8A—S3A | 112.0 (5) | C7B—C8B—S3B | 110.4 (5) |
C9A—C8A—S3A | 117.3 (5) | C9B—C8B—S3B | 117.4 (5) |
O4A—C9A—C10A | 123.1 (7) | O4B—C9B—C8B | 122.2 (7) |
O4A—C9A—C8A | 120.8 (7) | O4B—C9B—C10B | 121.4 (7) |
C10A—C9A—C8A | 116.1 (6) | C8B—C9B—C10B | 116.4 (6) |
C11A—C10A—C9A | 121.9 (7) | C11B—C10B—C9B | 123.1 (6) |
C11A—C10A—H10A | 119.0 | C11B—C10B—H10B | 118.5 |
C9A—C10A—H10A | 119.0 | C9B—C10B—H10B | 118.5 |
C10A—C11A—C12A | 128.0 (7) | C10B—C11B—C12B | 127.4 (6) |
C10A—C11A—H11A | 116.0 | C10B—C11B—H11B | 116.3 |
C12A—C11A—H11A | 116.0 | C12B—C11B—H11B | 116.3 |
C17A—C12A—C13A | 115.1 (6) | C17B—C12B—C13B | 116.6 (6) |
C17A—C12A—C11A | 124.1 (6) | C17B—C12B—C11B | 124.9 (6) |
C13A—C12A—C11A | 120.8 (6) | C13B—C12B—C11B | 118.4 (6) |
C14A—C13A—C12A | 121.8 (7) | C14B—C13B—C12B | 120.9 (7) |
C14A—C13A—H13A | 119.1 | C14B—C13B—H13B | 119.5 |
C12A—C13A—H13A | 119.1 | C12B—C13B—H13B | 119.5 |
C15A—C14A—C13A | 120.3 (7) | C15B—C14B—C13B | 120.6 (7) |
C15A—C14A—H14A | 119.9 | C15B—C14B—H14B | 119.7 |
C13A—C14A—H14A | 119.9 | C13B—C14B—H14B | 119.7 |
C14A—C15A—C16A | 120.5 (7) | C16B—C15B—C14B | 119.4 (7) |
C14A—C15A—H15A | 119.8 | C16B—C15B—H15B | 120.3 |
C16A—C15A—H15A | 119.8 | C14B—C15B—H15B | 120.3 |
C17A—C16A—C15A | 118.2 (7) | C15B—C16B—C17B | 120.2 (7) |
C17A—C16A—H16A | 120.9 | C15B—C16B—H16B | 119.9 |
C15A—C16A—H16A | 120.9 | C17B—C16B—H16B | 119.9 |
C12A—C17A—C16A | 124.1 (6) | C12B—C17B—C16B | 122.3 (6) |
C12A—C17A—Br2A | 120.4 (5) | C12B—C17B—Br2B | 119.7 (5) |
C16A—C17A—Br2A | 115.5 (5) | C16B—C17B—Br2B | 118.0 (6) |
C8A—S3A—C5A—C6A | −0.3 (5) | C8B—S3B—C5B—C6B | 1.0 (5) |
C8A—S3A—C5A—Br1A | −179.1 (4) | C8B—S3B—C5B—Br1B | −177.5 (4) |
S3A—C5A—C6A—C7A | 1.0 (8) | S3B—C5B—C6B—C7B | −1.3 (8) |
Br1A—C5A—C6A—C7A | 179.7 (5) | Br1B—C5B—C6B—C7B | 177.1 (5) |
C5A—C6A—C7A—C8A | −1.4 (9) | C5B—C6B—C7B—C8B | 1.0 (9) |
C6A—C7A—C8A—C9A | −178.8 (6) | C6B—C7B—C8B—C9B | −179.3 (7) |
C6A—C7A—C8A—S3A | 1.2 (8) | C6B—C7B—C8B—S3B | −0.2 (8) |
C5A—S3A—C8A—C7A | −0.5 (5) | C5B—S3B—C8B—C7B | −0.4 (5) |
C5A—S3A—C8A—C9A | 179.4 (5) | C5B—S3B—C8B—C9B | 178.8 (5) |
C7A—C8A—C9A—O4A | 176.7 (8) | C7B—C8B—C9B—O4B | −178.9 (8) |
S3A—C8A—C9A—O4A | −3.2 (9) | S3B—C8B—C9B—O4B | 2.1 (10) |
C7A—C8A—C9A—C10A | −1.3 (11) | C7B—C8B—C9B—C10B | 3.5 (11) |
S3A—C8A—C9A—C10A | 178.7 (5) | S3B—C8B—C9B—C10B | −175.5 (5) |
O4A—C9A—C10A—C11A | −2.6 (11) | O4B—C9B—C10B—C11B | 7.4 (12) |
C8A—C9A—C10A—C11A | 175.4 (6) | C8B—C9B—C10B—C11B | −175.0 (7) |
C9A—C10A—C11A—C12A | 176.2 (6) | C9B—C10B—C11B—C12B | −179.4 (7) |
C10A—C11A—C12A—C17A | 179.1 (7) | C10B—C11B—C12B—C17B | −154.3 (7) |
C10A—C11A—C12A—C13A | −1.7 (10) | C10B—C11B—C12B—C13B | 27.0 (11) |
C17A—C12A—C13A—C14A | 0.6 (10) | C17B—C12B—C13B—C14B | 1.6 (10) |
C11A—C12A—C13A—C14A | −178.6 (6) | C11B—C12B—C13B—C14B | −179.5 (7) |
C12A—C13A—C14A—C15A | 0.8 (11) | C12B—C13B—C14B—C15B | −1.4 (12) |
C13A—C14A—C15A—C16A | −0.4 (11) | C13B—C14B—C15B—C16B | −0.1 (13) |
C14A—C15A—C16A—C17A | −1.5 (10) | C14B—C15B—C16B—C17B | 1.3 (12) |
C13A—C12A—C17A—C16A | −2.6 (9) | C13B—C12B—C17B—C16B | −0.5 (10) |
C11A—C12A—C17A—C16A | 176.5 (6) | C11B—C12B—C17B—C16B | −179.2 (7) |
C13A—C12A—C17A—Br2A | 178.0 (5) | C13B—C12B—C17B—Br2B | −179.1 (5) |
C11A—C12A—C17A—Br2A | −2.9 (8) | C11B—C12B—C17B—Br2B | 2.2 (9) |
C15A—C16A—C17A—C12A | 3.1 (9) | C15B—C16B—C17B—C12B | −1.0 (11) |
C15A—C16A—C17A—Br2A | −177.4 (5) | C15B—C16B—C17B—Br2B | 177.6 (6) |
Experimental details
Crystal data | |
Chemical formula | C13H8Br2OS |
Mr | 372.07 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 293 |
a, b, c (Å) | 34.524 (8), 3.9994 (9), 23.428 (5) |
β (°) | 126.804 (3) |
V (Å3) | 2590.1 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 6.40 |
Crystal size (mm) | 0.22 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.228, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13574, 5988, 4266 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.109, 0.97 |
No. of reflections | 5988 |
No. of parameters | 308 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.58, −0.44 |
Absolute structure | Flack (1983), 2846 Friedel pairs |
Absolute structure parameter | 0.000 (13) |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012), WinGX (Farrugia, 2012).
Acknowledgements
The authors thank Professor T. N. Guru Row, SSCU, IISc, Bangalore, for the data collection. SBV thanks the Acharya Nagarjuna University, Guntur, Andhrapradesh, India, for the support of a part-time PhD in Pharmacy.
References
Alex, G., Srinivasan, S., Krishnasamy, V., Suresh, R. V., Iyer, R. & Iyer, P. R. (1993). Acta Cryst. C49, 70–72. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Li, Z. & Su, G. (1993). Acta Cryst. C49, 1075–1077. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Liang, Y.-S., Mu, S., Wang, J.-Y. & Liu, D.-K. (2011). Acta Cryst. E67, o830. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Pascard, C. (1995). Acta Cryst. D51, 407–417. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Thomas, A. H., Robert, B. M., Richard, A. F., Hege, S. B., Leah, L. F., Thomas, W. P. & Jay, L. B. (2004). J. Med. Chem. 47, 1750–1759. Web of Science CrossRef PubMed Google Scholar
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Apart from numerous applications in basic research, crystal structure conformation of small molecules has always been the choice for binding energy calculations in molecular modeling during drug discovery process (Pascard, 1995). The reason is it provides coordinates for the most favorable stereo positions of the atoms in solid state.Use of the low energy conformation obtained in this bound state may provide good rationality in drug design study. As a part of our effort in designing lead compound for human aldose reductase inhibiton we are interested in studying the crystal structure conformation of (2E)-1-(5-bromothiophen-2-yl)-3-[4-(dimethylamino) phenyl]prop-2-en-1-one. In our docking studies the title chalcone has shown good binding affinity with dock score -9.490027 calculated by using GLIDE scoring (Thomas et al., 2004) function from Schrodinger 9.2v molecular modeling suite.
The asymmetric unit of (2E)-1-(5-bromothiophen-2-yl)-3- (2-bromophenyl)prop-2-en-1-one, C13H8Br2OS, contain two molecules (Fig. 1). The five-membered thiophene rings (S3a\C5a\···C8a) & (S3b\C5b\···C8b) are not coplanar with the phenyl rings (C12a\C13a\···C17a) & (C12b\C13b\···C17b) system; the dihedral angle between the two planes are 10.5 (3)° and 33.2 (4)° of A and B molecules respectivelly. Bond distances and bond angles are in good agreement with those observed in related crystal structures (Liang et al., 2011; Alex et al., 1993; Li et al., 1993). The packing of molecules in the crystal structure is depicted in Fig. 2.