organic compounds
(2E)-1-(1,3-Benzodioxol-5-yl)-3-(2-bromophenyl)prop-2-en-1-one
aKey Laboratory of Science & Technology of Eco-Textiles, Ministry of Education, College of Chemistry, Chemical Engineering & Biotechnology, Donghua University, Shanghai 201620, People's Republic of China, bBioinformatics Infrastructure Facility, School of Life Science, University of Hyderabad, Hyderabad 500 046, India, cDepartment of Physics, Mangalore University, Mangalagangotri 574 199, India, dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and eDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India
*Correspondence e-mail: hongqili@dhu.edu.cn
The molecule of the title compound, C16H11BrO3, is essentially planar with a maximum deviation of 0.178 (4) Å and the configuration of the keto group with respect to the olefinic double bond is typically s-cis. In the intermolecular Br⋯O interactions [3.187 (3)Å] give rise to chains parallel to the b axis. Adjacent chains are further linked along the a axis by C—H⋯π interactions. The crystal studied was a racemic twin with a 0.595 (13):0.405 (13) ratio.
Related literature
For et al. (1999); Sarojini et al. (2006); Yarishkin et al. (2008). For halogen-bonding interactions, see: Thallapally et al. (2002); Metrangolo et al. (2005); Riley et al. (2009). For related structures, see: Harrison et al. (2006); Rathore et al. (2006); Li et al. (2008); Jasinski et al. (2010). For racemic see: Flack (1983); Flack & Bernardinelli (2000); Gömez et al. (2010).
see: Di CarloExperimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Supporting information
https://doi.org/10.1107/S1600536810015552/rz2432sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810015552/rz2432Isup2.hkl
The title compound was prepared as follows: to a mixture of 1-(1,3-benzodioxol-5-yl)ethanone (1.64 g, 0.01 mol) and 2-bromobenzaldehyde (1.85 g, 0.01 mol) in 30 ml ethanol, 10 ml of 10 % sodium hydroxide solution was added and stirred at 5-10° C for 3 hours. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Final yield 79%; m.p. 390-392° K. Crystals suitable for X-ray analysis were grown from (1:1 v/v) mixture of toluene and acetone by slow evaporation method. Anal.: calc. for C16H11BrO3 : C 58.03 , H 3.35; found: C 57.93, H 3.31.
All H atoms were stereochemically fixed and refined using a riding option with C(Sp2)—H = 0.93 Å, C(methylene)—H = 0.97 Å, and Uiso(H) = 1.2 Ueq(C). The residual electron density observed in the vicinity of Br is due to the result of rotation of the bromophenyl moiety about the C6—C7 bond. The disorder could not be reliably refined presumably due to very low occupancy of other conformers. The crystal studied was treated as an
leading to twin fractions of 0.595 (13):0.405 (13).Chalcones possess many interesting biological and pharmacological properties. They are highly reactive substances of varied nature. Recently, it is shown that few of the derivatives are able to block voltage-dependent potassium channels (Yarishkin et al., 2008).
have been also implicated in organic nonlinear optical materials for their SHG conversion efficiency (Sarojini et al., 2006). The radical quenching property of the phenolic groups present in many or chalcone-rich plant extracts has led to their use as drugs or food preservatives (Di Carlo et al., 1999). We earlier reported structures of chalcone derivatives (Harrison et al., 2006; Rathore et al., 2006; Jasinski et al., 2010; Li et al., 2008). In continuation of the study, we have synthesized a new chalcone analog, C16H11BrO3, (I), and discuss its crytal structure herein.The crystal of (I) studied was racemically twinned in a 0.595 (13):0.405 (13) ratio. Similar racemic
in Br-containing compounds was observed by Gömez et al. (2010). The skeleton of (I) is essentially planar possessing two intramolecular short contacts. The bifurcated C1—H7···(Br1, O1) promote planarity of the molecular skeleton (Table 1). The configuration of the keto group with respect to the olefinic double bond is typically s-cis, with the C7—C8—C9—O1 torsion angle of -1.6 (7)° (Rathore et al., 2006).Crystal packing is characterized by halogen···oxygen interactions between molecules related by 2-fold screw axis, with the Br1 ···O2i distance of 3.187 (3)Å [symmetry code (i): 0.5+x, 0.5-y, -z] and the C1—Br1···O2 angle of 170.6 (1)°. The Br···O interaction leads to a one-dimensional chain along b axis. Crystal packing is shown in Fig 2. Br···O interactions have previously been employed for crystal engineering purposes (Thallapally et al., 2002). Halogen bonding between halogen atoms (Lewis acid) and neutral or anionic π short contact, giving rise to an alternate linear pattern along the a axis (Table 1).
has been subject of great interest in recent years, primarily due to their unique noncovalent bonding characteristics (Metrangolo et al., 2005; Riley et al., 2009). The additionally contains a C—H···For
see: Di Carlo et al. (1999); Sarojini et al. (2006); Yarishkin et al. (2008). For halogen-bonding interactions, see: Thallapally et al. (2002); Metrangolo et al. (2005); Riley et al. (2009). For related structures, see: Harrison et al. (2006); Rathore et al. (2006); Li et al. (2008); Jasinski et al. (2010). For racemic see: Flack (1983); Flack & Bernardinelli (2000); Gömez et al. (2010).Data collection: SMART (Bruker, 2004); cell
SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C16H11BrO3 | Dx = 1.614 Mg m−3 |
Mr = 331.16 | Melting point = 390–392 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 7488 reflections |
a = 5.0434 (2) Å | θ = 2.5–25.7° |
b = 12.9354 (4) Å | µ = 3.02 mm−1 |
c = 20.8916 (7) Å | T = 296 K |
V = 1362.93 (8) Å3 | Block, colorless |
Z = 4 | 0.53 × 0.19 × 0.16 mm |
F(000) = 664 |
Bruker SMART APEXII CCD area-detector diffractometer | 2674 independent reflections |
Radiation source: fine-focus sealed tube | 2437 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −6→6 |
Tmin = 0.576, Tmax = 0.653 | k = −13→15 |
17031 measured reflections | l = −25→25 |
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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0412P)2 + 0.7667P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2674 reflections | Δρmax = 0.64 e Å−3 |
182 parameters | Δρmin = −0.52 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1086 Bijvoet pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.595 (13) |
C16H11BrO3 | V = 1362.93 (8) Å3 |
Mr = 331.16 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.0434 (2) Å | µ = 3.02 mm−1 |
b = 12.9354 (4) Å | T = 296 K |
c = 20.8916 (7) Å | 0.53 × 0.19 × 0.16 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 2674 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2437 reflections with I > 2σ(I) |
Tmin = 0.576, Tmax = 0.653 | Rint = 0.023 |
17031 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.086 | Δρmax = 0.64 e Å−3 |
S = 1.06 | Δρmin = −0.52 e Å−3 |
2674 reflections | Absolute structure: Flack (1983), 1086 Bijvoet pairs |
182 parameters | Absolute structure parameter: 0.595 (13) |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | ||
Br1 | 0.74414 (9) | 0.52368 (3) | 0.425085 (18) | 0.07369 (16) | |
O1 | 0.0651 (6) | 0.5167 (2) | 0.25271 (15) | 0.0779 (9) | |
O2 | −0.6166 (5) | 0.26394 (18) | 0.06042 (12) | 0.0586 (6) | |
O3 | −0.6165 (5) | 0.44083 (18) | 0.07678 (11) | 0.0554 (5) | |
C1 | 0.7744 (7) | 0.3802 (2) | 0.40661 (13) | 0.0493 (7) | |
C2 | 0.9616 (7) | 0.3239 (3) | 0.44092 (16) | 0.0610 (9) | |
H2 | 1.0660 | 0.3561 | 0.4717 | 0.073* | |
C3 | 0.9903 (8) | 0.2201 (3) | 0.42877 (19) | 0.0679 (11) | |
H3 | 1.1121 | 0.1813 | 0.4520 | 0.081* | |
C4 | 0.8394 (8) | 0.1738 (3) | 0.3824 (2) | 0.0661 (10) | |
H4 | 0.8595 | 0.1036 | 0.3741 | 0.079* | |
C5 | 0.6594 (7) | 0.2304 (3) | 0.34812 (17) | 0.0576 (9) | |
H5 | 0.5603 | 0.1975 | 0.3166 | 0.069* | |
C6 | 0.6196 (6) | 0.3355 (3) | 0.35892 (14) | 0.0461 (7) | |
C7 | 0.4282 (7) | 0.3947 (3) | 0.32148 (16) | 0.0533 (8) | |
H7 | 0.4276 | 0.4658 | 0.3280 | 0.064* | |
C8 | 0.2596 (7) | 0.3595 (2) | 0.28037 (14) | 0.0524 (7) | |
H8 | 0.2561 | 0.2885 | 0.2732 | 0.063* | |
C9 | 0.0717 (6) | 0.4246 (3) | 0.24404 (15) | 0.0461 (7) | |
C10 | −0.1054 (6) | 0.3754 (2) | 0.19621 (13) | 0.0413 (6) | |
C11 | −0.1108 (7) | 0.2691 (3) | 0.18603 (16) | 0.0486 (7) | |
H11 | 0.0015 | 0.2268 | 0.2097 | 0.058* | |
C12 | −0.2804 (7) | 0.2245 (2) | 0.14116 (15) | 0.0522 (8) | |
H12 | −0.2842 | 0.1534 | 0.1347 | 0.063* | |
C13 | −0.4395 (6) | 0.2889 (2) | 0.10737 (14) | 0.0436 (7) | |
C14 | −0.4375 (6) | 0.3942 (2) | 0.11713 (13) | 0.0398 (6) | |
C15 | −0.2737 (7) | 0.4401 (2) | 0.16089 (12) | 0.0430 (6) | |
H15 | −0.2739 | 0.5113 | 0.1670 | 0.052* | |
C16 | −0.7382 (8) | 0.3593 (2) | 0.04180 (13) | 0.0498 (7) | |
H16A | −0.7151 | 0.3704 | −0.0038 | 0.060* | |
H16B | −0.9267 | 0.3572 | 0.0510 | 0.060* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0729 (2) | 0.0700 (2) | 0.0781 (3) | 0.0085 (2) | −0.0259 (2) | −0.02381 (18) |
O1 | 0.096 (2) | 0.0487 (15) | 0.0889 (19) | 0.0021 (15) | −0.0448 (17) | −0.0083 (14) |
O2 | 0.0621 (14) | 0.0532 (13) | 0.0605 (13) | 0.0012 (11) | −0.0161 (12) | −0.0129 (11) |
O3 | 0.0580 (13) | 0.0492 (12) | 0.0589 (13) | 0.0062 (11) | −0.0187 (11) | −0.0013 (11) |
C1 | 0.0454 (16) | 0.0575 (17) | 0.0449 (14) | −0.0019 (17) | 0.0005 (14) | 0.0032 (12) |
C2 | 0.0490 (18) | 0.088 (3) | 0.0466 (17) | 0.0060 (18) | −0.0039 (15) | 0.0082 (18) |
C3 | 0.057 (2) | 0.083 (3) | 0.064 (2) | 0.0180 (19) | 0.0026 (19) | 0.027 (2) |
C4 | 0.064 (2) | 0.054 (2) | 0.081 (2) | 0.0069 (16) | 0.0111 (19) | 0.017 (2) |
C5 | 0.056 (2) | 0.056 (2) | 0.0608 (19) | −0.0020 (15) | 0.0003 (16) | 0.0071 (17) |
C6 | 0.0418 (15) | 0.0552 (19) | 0.0415 (15) | −0.0003 (15) | 0.0029 (12) | 0.0046 (13) |
C7 | 0.0564 (19) | 0.0461 (18) | 0.0575 (18) | 0.0046 (15) | −0.0111 (16) | −0.0041 (15) |
C8 | 0.0509 (16) | 0.0510 (16) | 0.0553 (16) | −0.003 (2) | −0.0075 (18) | −0.0004 (13) |
C9 | 0.0473 (17) | 0.0479 (19) | 0.0432 (15) | −0.0038 (15) | −0.0021 (13) | −0.0006 (13) |
C10 | 0.0411 (15) | 0.0450 (16) | 0.0378 (13) | −0.0004 (13) | 0.0037 (12) | 0.0025 (13) |
C11 | 0.0464 (17) | 0.0473 (18) | 0.0522 (17) | 0.0055 (15) | −0.0052 (15) | 0.0026 (15) |
C12 | 0.058 (2) | 0.0368 (14) | 0.0621 (17) | −0.0016 (17) | −0.0073 (18) | −0.0041 (13) |
C13 | 0.0435 (16) | 0.0458 (17) | 0.0415 (14) | −0.0033 (13) | 0.0011 (13) | −0.0046 (13) |
C14 | 0.0371 (14) | 0.0441 (16) | 0.0383 (13) | 0.0011 (12) | 0.0031 (12) | 0.0026 (12) |
C15 | 0.0463 (16) | 0.0397 (13) | 0.0429 (13) | −0.0003 (16) | −0.0004 (13) | −0.0022 (11) |
C16 | 0.0492 (16) | 0.0540 (17) | 0.0463 (14) | −0.005 (2) | −0.0056 (16) | 0.0007 (12) |
Br1—C1 | 1.902 (3) | C7—C8 | 1.292 (5) |
O1—C9 | 1.206 (4) | C7—H7 | 0.9300 |
O2—C13 | 1.365 (4) | C8—C9 | 1.478 (5) |
O2—C16 | 1.431 (4) | C8—H8 | 0.9300 |
O3—C14 | 1.374 (4) | C9—C10 | 1.484 (4) |
O3—C16 | 1.423 (4) | C10—C11 | 1.391 (4) |
C1—C2 | 1.391 (5) | C10—C15 | 1.402 (4) |
C1—C6 | 1.392 (4) | C11—C12 | 1.394 (4) |
C2—C3 | 1.374 (6) | C11—H11 | 0.9300 |
C2—H2 | 0.9300 | C12—C13 | 1.355 (4) |
C3—C4 | 1.371 (6) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—C14 | 1.378 (4) |
C4—C5 | 1.368 (5) | C14—C15 | 1.368 (4) |
C4—H4 | 0.9300 | C15—H15 | 0.9300 |
C5—C6 | 1.393 (5) | C16—H16A | 0.9700 |
C5—H5 | 0.9300 | C16—H16B | 0.9700 |
C6—C7 | 1.459 (4) | ||
C13—O2—C16 | 105.8 (2) | O1—C9—C10 | 120.6 (3) |
C14—O3—C16 | 105.9 (2) | C8—C9—C10 | 119.1 (3) |
C2—C1—C6 | 122.1 (3) | C11—C10—C15 | 119.9 (3) |
C2—C1—Br1 | 117.4 (3) | C11—C10—C9 | 122.6 (3) |
C6—C1—Br1 | 120.4 (2) | C15—C10—C9 | 117.5 (3) |
C3—C2—C1 | 119.2 (4) | C10—C11—C12 | 121.6 (3) |
C3—C2—H2 | 120.4 | C10—C11—H11 | 119.2 |
C1—C2—H2 | 120.4 | C12—C11—H11 | 119.2 |
C4—C3—C2 | 120.0 (3) | C13—C12—C11 | 117.3 (3) |
C4—C3—H3 | 120.0 | C13—C12—H12 | 121.3 |
C2—C3—H3 | 120.0 | C11—C12—H12 | 121.3 |
C5—C4—C3 | 120.3 (4) | C12—C13—O2 | 128.1 (3) |
C5—C4—H4 | 119.9 | C12—C13—C14 | 121.8 (3) |
C3—C4—H4 | 119.9 | O2—C13—C14 | 110.2 (3) |
C4—C5—C6 | 122.2 (4) | C15—C14—O3 | 128.0 (3) |
C4—C5—H5 | 118.9 | C15—C14—C13 | 122.2 (3) |
C6—C5—H5 | 118.9 | O3—C14—C13 | 109.8 (3) |
C1—C6—C5 | 116.2 (3) | C14—C15—C10 | 117.3 (3) |
C1—C6—C7 | 122.4 (3) | C14—C15—H15 | 121.4 |
C5—C6—C7 | 121.4 (3) | C10—C15—H15 | 121.4 |
C8—C7—C6 | 127.4 (3) | O3—C16—O2 | 108.3 (2) |
C8—C7—H7 | 116.3 | O3—C16—H16A | 110.0 |
C6—C7—H7 | 116.3 | O2—C16—H16A | 110.0 |
C7—C8—C9 | 124.3 (3) | O3—C16—H16B | 110.0 |
C7—C8—H8 | 117.9 | O2—C16—H16B | 110.0 |
C9—C8—H8 | 117.9 | H16A—C16—H16B | 108.4 |
O1—C9—C8 | 120.3 (3) | ||
C6—C1—C2—C3 | −1.8 (5) | C15—C10—C11—C12 | 0.1 (5) |
Br1—C1—C2—C3 | −179.7 (3) | C9—C10—C11—C12 | 179.5 (3) |
C1—C2—C3—C4 | 1.4 (5) | C10—C11—C12—C13 | 0.4 (5) |
C2—C3—C4—C5 | −0.2 (6) | C11—C12—C13—O2 | 178.6 (3) |
C3—C4—C5—C6 | −0.6 (6) | C11—C12—C13—C14 | −0.7 (5) |
C2—C1—C6—C5 | 1.0 (5) | C16—O2—C13—C12 | 178.4 (3) |
Br1—C1—C6—C5 | 178.8 (2) | C16—O2—C13—C14 | −2.3 (3) |
C2—C1—C6—C7 | −178.2 (3) | C16—O3—C14—C15 | −179.3 (3) |
Br1—C1—C6—C7 | −0.4 (4) | C16—O3—C14—C13 | 1.5 (3) |
C4—C5—C6—C1 | 0.2 (5) | C12—C13—C14—C15 | 0.6 (5) |
C4—C5—C6—C7 | 179.4 (3) | O2—C13—C14—C15 | −178.8 (3) |
C1—C6—C7—C8 | −173.5 (4) | C12—C13—C14—O3 | 180.0 (3) |
C5—C6—C7—C8 | 7.4 (6) | O2—C13—C14—O3 | 0.5 (4) |
C6—C7—C8—C9 | −179.8 (3) | O3—C14—C15—C10 | −179.3 (3) |
C7—C8—C9—O1 | −1.5 (6) | C13—C14—C15—C10 | −0.1 (4) |
C7—C8—C9—C10 | 177.6 (3) | C11—C10—C15—C14 | −0.2 (4) |
O1—C9—C10—C11 | −177.9 (4) | C9—C10—C15—C14 | −179.7 (3) |
C8—C9—C10—C11 | 3.0 (4) | C14—O3—C16—O2 | −2.8 (3) |
O1—C9—C10—C15 | 1.5 (5) | C13—O2—C16—O3 | 3.1 (3) |
C8—C9—C10—C15 | −177.6 (3) |
Cg3 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Br1 | 0.93 | 2.69 | 3.164 (4) | 113 |
C7—H7···O1 | 0.93 | 2.50 | 2.812 (6) | 100 |
C16—H16B···Cg3i | 0.97 | 2.76 | 3.563 (4) | 141 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H11BrO3 |
Mr | 331.16 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 296 |
a, b, c (Å) | 5.0434 (2), 12.9354 (4), 20.8916 (7) |
V (Å3) | 1362.93 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 3.02 |
Crystal size (mm) | 0.53 × 0.19 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2004) |
Tmin, Tmax | 0.576, 0.653 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17031, 2674, 2437 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.086, 1.06 |
No. of reflections | 2674 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.52 |
Absolute structure | Flack (1983), 1086 Bijvoet pairs |
Absolute structure parameter | 0.595 (13) |
Computer programs: SMART (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
Cg3 is the centroid of the C10–C15 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···Br1 | 0.93 | 2.69 | 3.164 (4) | 113 |
C7—H7···O1 | 0.93 | 2.50 | 2.812 (6) | 100 |
C16—H16B···Cg3i | 0.97 | 2.76 | 3.563 (4) | 141 |
Symmetry code: (i) x−1, y, z. |
Acknowledgements
Mangalore University and the Bioinformatics Infrastructure Facility, University of Hyderabad, are gratefully acknowledged. BN thanks UGC–SAP for financial support. RSR thanks the CSIR, New Delhi, for support under the scientist's pool scheme.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Chalcones possess many interesting biological and pharmacological properties. They are highly reactive substances of varied nature. Recently, it is shown that few of the derivatives are able to block voltage-dependent potassium channels (Yarishkin et al., 2008). Chalcones have been also implicated in organic nonlinear optical materials for their SHG conversion efficiency (Sarojini et al., 2006). The radical quenching property of the phenolic groups present in many chalcones or chalcone-rich plant extracts has led to their use as drugs or food preservatives (Di Carlo et al., 1999). We earlier reported structures of chalcone derivatives (Harrison et al., 2006; Rathore et al., 2006; Jasinski et al., 2010; Li et al., 2008). In continuation of the study, we have synthesized a new chalcone analog, C16H11BrO3, (I), and discuss its crytal structure herein.
The crystal of (I) studied was racemically twinned in a 0.595 (13):0.405 (13) ratio. Similar racemic twinning in Br-containing compounds was observed by Gömez et al. (2010). The skeleton of (I) is essentially planar possessing two intramolecular short contacts. The bifurcated C1—H7···(Br1, O1) promote planarity of the molecular skeleton (Table 1). The configuration of the keto group with respect to the olefinic double bond is typically s-cis, with the C7—C8—C9—O1 torsion angle of -1.6 (7)° (Rathore et al., 2006).
Crystal packing is characterized by halogen···oxygen interactions between molecules related by 2-fold screw axis, with the Br1 ···O2i distance of 3.187 (3)Å [symmetry code (i): 0.5+x, 0.5-y, -z] and the C1—Br1···O2 angle of 170.6 (1)°. The Br···O interaction leads to a one-dimensional chain along b axis. Crystal packing is shown in Fig 2. Br···O interactions have previously been employed for crystal engineering purposes (Thallapally et al., 2002). Halogen bonding between halogen atoms (Lewis acid) and neutral or anionic Lewis base, has been subject of great interest in recent years, primarily due to their unique noncovalent bonding characteristics (Metrangolo et al., 2005; Riley et al., 2009). The crystal structure additionally contains a C—H···π short contact, giving rise to an alternate linear pattern along the a axis (Table 1).