organic compounds
(E)-1-(3-Bromophenyl)-3-(4-nitrophenyl)prop-2-en-1-one
aDepartment of Chemistry, Sir M.V. PG Center, University of Mysore, Tubinakere, Mandya 571 402, India, bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800 USM, Malaysia, cDepartment of Engineering Chemistry, Vidya Vikas Institute of Engineering and Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570 028, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, eInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, and fDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
*Correspondence e-mail: chidankumar@gmail.com, khalil.i@najah.edu
The title compound, C15H10BrNO3, is close to planar, as seen by the dihedral angle of 3.32 (17)° between the bromophenyl and nitrophenyl rings. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming chains propagating along the c-axis direction.
Keywords: crystal structure; chalcone; hydrogen bonds.
CCDC reference: 1036742
Structure description
et al., 2015), photonics and optoelectronics. They are also considered to be the precursors of and Owing to their electronic structure, also find unique applications as fluorescent probes for sensing metal ions (Kumar et al. 2013). In a continuation of our work on the synthesis of new and studies of their NLO properties (Tejkiran et al., 2016; Chidan et al. 2016), we report here the of the title compound.
have attracted considerable interest because of their major applications in technologies such as optical computing and optical communication systems (ChidanThe structure of the molecule is shown in Fig. 1. The molecule is nearly planar, with a dihedral angle of 3.32 (17)° between the bromophenyl and the nitrophenyl rings that are bridged by the enone unit. This value is less than the value of 19.13 (15)° reported earlier between the aromatic rings in the related chalcone derivative (E)-3-(2,3-dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (Naveen et al., 2016). The carbonyl group at C7 lies close to the plane of the olefinic double bond and bromophenyl ring as indicated by the O1—C7—C8—C9 and O1—C7—C6—C5 torsion angles of −3.9 (6) and 5.2 (5)° respectively.
In the crystal, the molecules are linked via weak C—H⋯O hydrogen bonds (Table 1), forming chains propagating along the c-axis direction, Fig. 2.
Synthesis and crystallization
2-Bromoacetophenone (1.99 g, 0.01 mol) was mixed with 4-nitrobenzaldehyde (1.51 g, 0.01 mol) and dissolved in methanol (20 ml). To this, a catalytic amount of NaOH was added slowly, drop-by-drop with constant stirring. The reaction mixture was stirred for 4 h. The resulting crude solid was filtered, washed with distilled water and finally recrystallized from methanol to give the pure chalcone. Single crystals suitable for X-ray diffraction studies were grown by slow evaporation of an acetone solution (m.p. 324–325 K).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1036742
https://doi.org/10.1107/S2414314617002875/sj4092sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617002875/sj4092Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314617002875/sj4092Isup3.cml
Data collection: CrystalClear SM-Expert (Rigaku, 2011); cell
CrystalClear SM-Expert (Rigaku, 2011); data reduction: CrystalClear SM-Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).C15H10BrNO3 | F(000) = 332 |
Mr = 332.14 | Dx = 1.660 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2325 reflections |
a = 6.0511 (7) Å | θ = 1.9–26.1° |
b = 5.0542 (6) Å | µ = 3.10 mm−1 |
c = 21.841 (3) Å | T = 294 K |
β = 95.781 (2)° | Rectangle, brown |
V = 664.58 (14) Å3 | 0.49 × 0.28 × 0.10 mm |
Z = 2 |
Rigaku Saturn724+ diffractometer | 2605 independent reflections |
Radiation source: fine-focus sealed tube | 2325 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
Detector resolution: 18.4 pixels mm-1 | θmax = 26.1°, θmin = 1.9° |
profile data from ω–scans | h = −7→7 |
Absorption correction: multi-scan (NUMABS; Rigaku, 1999) | k = −6→6 |
Tmin = 0.312, Tmax = 0.751 | l = −27→24 |
8418 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)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0421P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2605 reflections | Δρmax = 0.59 e Å−3 |
181 parameters | Δρmin = −0.40 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.028 (11) |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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 | 0.10940 (5) | 1.49979 (11) | 0.55889 (2) | 0.0536 (1) | |
O1 | 0.1299 (4) | 0.7918 (8) | 0.74119 (13) | 0.0805 (13) | |
O2 | 0.8278 (4) | −0.4766 (7) | 0.98538 (11) | 0.0523 (8) | |
O3 | 1.0879 (4) | −0.4357 (5) | 0.92554 (12) | 0.0544 (10) | |
N1 | 0.9084 (4) | −0.3727 (6) | 0.94205 (13) | 0.0397 (9) | |
C1 | 0.5966 (6) | 0.8764 (8) | 0.65218 (17) | 0.0499 (11) | |
C2 | 0.6499 (5) | 1.0205 (12) | 0.60163 (17) | 0.0576 (13) | |
C3 | 0.5076 (6) | 1.1998 (8) | 0.57345 (18) | 0.0522 (12) | |
C4 | 0.3066 (5) | 1.2470 (7) | 0.59803 (15) | 0.0405 (11) | |
C5 | 0.2521 (6) | 1.1097 (7) | 0.64856 (17) | 0.0401 (11) | |
C6 | 0.3956 (5) | 0.9202 (6) | 0.67594 (16) | 0.0384 (11) | |
C7 | 0.3196 (6) | 0.7626 (8) | 0.72774 (16) | 0.0461 (12) | |
C8 | 0.4693 (6) | 0.5698 (7) | 0.76037 (16) | 0.0470 (14) | |
C9 | 0.4138 (6) | 0.4312 (7) | 0.80724 (17) | 0.0435 (13) | |
C10 | 0.5470 (5) | 0.2282 (7) | 0.84194 (15) | 0.0359 (10) | |
C11 | 0.4689 (5) | 0.1157 (7) | 0.89396 (16) | 0.0409 (10) | |
C12 | 0.5857 (5) | −0.0774 (6) | 0.92742 (17) | 0.0375 (11) | |
C13 | 0.7850 (5) | −0.1623 (6) | 0.90817 (15) | 0.0326 (10) | |
C14 | 0.8681 (5) | −0.0549 (7) | 0.85751 (16) | 0.0421 (13) | |
C15 | 0.7494 (6) | 0.1405 (7) | 0.82458 (16) | 0.0434 (11) | |
H1A | 0.69530 | 0.75090 | 0.67010 | 0.0600* | |
H2A | 0.78680 | 0.99340 | 0.58670 | 0.0690* | |
H3A | 0.54270 | 1.28940 | 0.53850 | 0.0630* | |
H5A | 0.11820 | 1.14370 | 0.66450 | 0.0480* | |
H8A | 0.60940 | 0.54470 | 0.74730 | 0.0560* | |
H9A | 0.27440 | 0.46550 | 0.81990 | 0.0530* | |
H11A | 0.33430 | 0.17310 | 0.90630 | 0.0490* | |
H12A | 0.53230 | −0.14960 | 0.96220 | 0.0450* | |
H14A | 1.00300 | −0.11330 | 0.84550 | 0.0510* | |
H15A | 0.80550 | 0.21450 | 0.79040 | 0.0520* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0622 (2) | 0.0424 (2) | 0.0541 (2) | 0.0079 (2) | −0.0041 (2) | 0.0068 (2) |
O1 | 0.0605 (17) | 0.120 (3) | 0.066 (2) | 0.0404 (18) | 0.0305 (15) | 0.0444 (19) |
O2 | 0.0533 (12) | 0.0489 (16) | 0.0559 (14) | 0.0060 (14) | 0.0111 (10) | 0.0179 (16) |
O3 | 0.0488 (13) | 0.052 (2) | 0.0643 (17) | 0.0202 (11) | 0.0158 (12) | 0.0045 (12) |
N1 | 0.0420 (16) | 0.0328 (15) | 0.0434 (18) | 0.0072 (11) | −0.0004 (13) | −0.0078 (12) |
C1 | 0.0431 (18) | 0.054 (2) | 0.052 (2) | 0.0101 (16) | 0.0022 (17) | 0.0085 (17) |
C2 | 0.0443 (17) | 0.065 (3) | 0.066 (2) | 0.006 (2) | 0.0182 (15) | 0.016 (3) |
C3 | 0.051 (2) | 0.054 (2) | 0.053 (2) | −0.0019 (19) | 0.0127 (17) | 0.0123 (19) |
C4 | 0.0490 (19) | 0.0328 (18) | 0.0381 (19) | 0.0016 (14) | −0.0038 (15) | 0.0002 (14) |
C5 | 0.0385 (17) | 0.0447 (19) | 0.037 (2) | 0.0058 (14) | 0.0032 (15) | −0.0062 (14) |
C6 | 0.0427 (18) | 0.040 (2) | 0.0321 (18) | 0.0037 (13) | 0.0024 (14) | −0.0023 (12) |
C7 | 0.049 (2) | 0.052 (2) | 0.037 (2) | 0.0157 (17) | 0.0036 (16) | −0.0008 (16) |
C8 | 0.0482 (19) | 0.053 (3) | 0.041 (2) | 0.0103 (16) | 0.0100 (16) | 0.0053 (15) |
C9 | 0.0398 (16) | 0.049 (3) | 0.042 (2) | 0.0085 (14) | 0.0052 (15) | −0.0002 (14) |
C10 | 0.0390 (16) | 0.0366 (18) | 0.0328 (18) | 0.0010 (14) | 0.0065 (13) | 0.0016 (13) |
C11 | 0.0342 (16) | 0.0449 (18) | 0.045 (2) | 0.0069 (14) | 0.0108 (15) | 0.0003 (15) |
C12 | 0.0398 (16) | 0.034 (2) | 0.0403 (19) | 0.0021 (12) | 0.0120 (14) | 0.0030 (12) |
C13 | 0.0336 (15) | 0.0270 (17) | 0.0370 (18) | 0.0019 (12) | 0.0027 (13) | 0.0000 (13) |
C14 | 0.0339 (15) | 0.050 (3) | 0.044 (2) | 0.0070 (14) | 0.0117 (14) | −0.0025 (15) |
C15 | 0.0463 (19) | 0.047 (2) | 0.039 (2) | 0.0014 (15) | 0.0140 (16) | 0.0061 (16) |
Br1—C4 | 1.893 (3) | C10—C15 | 1.391 (5) |
O1—C7 | 1.222 (4) | C11—C12 | 1.372 (5) |
O2—N1 | 1.226 (4) | C12—C13 | 1.385 (4) |
O3—N1 | 1.221 (4) | C13—C14 | 1.373 (5) |
N1—C13 | 1.458 (4) | C14—C15 | 1.380 (5) |
C1—C2 | 1.388 (6) | C1—H1A | 0.9300 |
C1—C6 | 1.387 (5) | C2—H2A | 0.9300 |
C2—C3 | 1.355 (6) | C3—H3A | 0.9300 |
C3—C4 | 1.399 (5) | C5—H5A | 0.9300 |
C4—C5 | 1.372 (5) | C8—H8A | 0.9300 |
C5—C6 | 1.387 (5) | C9—H9A | 0.9300 |
C6—C7 | 1.494 (5) | C11—H11A | 0.9300 |
C7—C8 | 1.466 (5) | C12—H12A | 0.9300 |
C8—C9 | 1.312 (5) | C14—H14A | 0.9300 |
C9—C10 | 1.468 (5) | C15—H15A | 0.9300 |
C10—C11 | 1.395 (5) | ||
O2—N1—O3 | 123.5 (3) | N1—C13—C14 | 119.2 (3) |
O2—N1—C13 | 118.8 (3) | C12—C13—C14 | 121.6 (3) |
O3—N1—C13 | 117.8 (3) | C13—C14—C15 | 119.3 (3) |
C2—C1—C6 | 119.8 (3) | C10—C15—C14 | 120.8 (3) |
C1—C2—C3 | 121.7 (3) | C2—C1—H1A | 120.00 |
C2—C3—C4 | 118.5 (3) | C6—C1—H1A | 120.00 |
Br1—C4—C3 | 118.4 (3) | C1—C2—H2A | 119.00 |
Br1—C4—C5 | 120.9 (2) | C3—C2—H2A | 119.00 |
C3—C4—C5 | 120.8 (3) | C2—C3—H3A | 121.00 |
C4—C5—C6 | 120.4 (3) | C4—C3—H3A | 121.00 |
C1—C6—C5 | 118.9 (3) | C4—C5—H5A | 120.00 |
C1—C6—C7 | 123.1 (3) | C6—C5—H5A | 120.00 |
C5—C6—C7 | 117.9 (3) | C7—C8—H8A | 119.00 |
O1—C7—C6 | 119.1 (3) | C9—C8—H8A | 119.00 |
O1—C7—C8 | 120.9 (4) | C8—C9—H9A | 116.00 |
C6—C7—C8 | 120.0 (3) | C10—C9—H9A | 116.00 |
C7—C8—C9 | 122.7 (3) | C10—C11—H11A | 119.00 |
C8—C9—C10 | 127.3 (3) | C12—C11—H11A | 119.00 |
C9—C10—C11 | 119.5 (3) | C11—C12—H12A | 121.00 |
C9—C10—C15 | 122.4 (3) | C13—C12—H12A | 121.00 |
C11—C10—C15 | 118.2 (3) | C13—C14—H14A | 120.00 |
C10—C11—C12 | 121.7 (3) | C15—C14—H14A | 120.00 |
C11—C12—C13 | 118.5 (3) | C10—C15—H15A | 120.00 |
N1—C13—C12 | 119.3 (3) | C14—C15—H15A | 120.00 |
O2—N1—C13—C12 | 2.9 (5) | C5—C6—C7—C8 | −176.8 (3) |
O2—N1—C13—C14 | −176.4 (3) | O1—C7—C8—C9 | −3.9 (6) |
O3—N1—C13—C12 | −177.0 (3) | C6—C7—C8—C9 | 178.1 (3) |
O3—N1—C13—C14 | 3.7 (4) | C7—C8—C9—C10 | 178.0 (3) |
C6—C1—C2—C3 | −1.8 (7) | C8—C9—C10—C11 | 174.7 (4) |
C2—C1—C6—C5 | −0.4 (6) | C8—C9—C10—C15 | −5.9 (6) |
C2—C1—C6—C7 | 176.2 (4) | C9—C10—C11—C12 | 179.1 (3) |
C1—C2—C3—C4 | 2.8 (7) | C15—C10—C11—C12 | −0.4 (5) |
C2—C3—C4—Br1 | 179.5 (3) | C9—C10—C15—C14 | −178.6 (3) |
C2—C3—C4—C5 | −1.7 (6) | C11—C10—C15—C14 | 0.8 (5) |
Br1—C4—C5—C6 | 178.4 (3) | C10—C11—C12—C13 | −0.6 (5) |
C3—C4—C5—C6 | −0.4 (5) | C11—C12—C13—N1 | −178.2 (3) |
C4—C5—C6—C1 | 1.4 (5) | C11—C12—C13—C14 | 1.1 (5) |
C4—C5—C6—C7 | −175.4 (3) | N1—C13—C14—C15 | 178.7 (3) |
C1—C6—C7—O1 | −171.4 (4) | C12—C13—C14—C15 | −0.6 (5) |
C1—C6—C7—C8 | 6.6 (5) | C13—C14—C15—C10 | −0.3 (5) |
C5—C6—C7—O1 | 5.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H11A···O3i | 0.93 | 2.54 | 3.354 (4) | 147 |
C14—H14A···O1ii | 0.93 | 2.52 | 3.221 (4) | 132 |
Symmetry codes: (i) x−1, y+1, z; (ii) x+1, y−1, z. |
Acknowledgements
The authors extend their appreciation to the Vidya Vikas Research & Development Center for facilities and encouragement. CKQ thanks the Malaysian Government and USM for a Research University Individual (RUI) Grant (1001/PFIZIK/811278).
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