(E)-1-(3-Bromo­phen­yl)-3-(4-nitro­phen­yl)prop-2-en-1-one

Harini, K.S.; Quah, C.K.; Chidan Kumar, C.S.; Chandraju, S.; Lokanath, N.K.; Naveen, S.; Warad, I.

doi:10.1107/S2414314617002875

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170287

https://doi.org/10.1107/S2414314617002875

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(E)-1-(3-Bromophenyl)-3-(4-nitrophenyl)prop-2-en-1-one

K. S. Harini,^a Ching Kheng Quah,^b C. S. Chidan Kumar,^c ^* S. Chandraju,^a N. K. Lokanath,^d S. Naveen ^e and Ismail Warad ^f ^*

^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

Edited by J. Simpson, University of Otago, New Zealand (Received 19 February 2017; accepted 20 February 2017; online 24 February 2017)

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

Chalcones have attracted considerable interest because of their major applications in technologies such as optical computing and optical communication systems (Chidan et al., 2015 ), photonics and optoelectronics. They are also considered to be the precursors of flavonoids and isoflavonoids. Owing to their electronic structure, chalcones 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 chalcones and studies of their NLO properties (Tejkiran et al., 2016 ; Chidan et al. 2016 ), we report here the crystal structure of the title compound.

The 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.

Figure 1
The molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

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.

Table 1
Hydrogen-bond geometry (Å, °)

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.

Figure 2
The packing of the molecules, viewed along the a axis, with hydrogen bonds drawn as dashed lines.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrNO₃
M_r	332.14
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	294
a, b, c (Å)	6.0511 (7), 5.0542 (6), 21.841 (3)
β (°)	95.781 (2)
V (Å³)	664.58 (14)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	3.10
Crystal size (mm)	0.49 × 0.28 × 0.10

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (NUMABS; Rigaku, 1999 )
T_min, T_max	0.312, 0.751
No. of measured, independent and observed [I > 2σ(I)] reflections	8418, 2605, 2325
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.083, 1.06
No. of reflections	2605
No. of parameters	181
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.40
Absolute structure	Flack (1983 )
Absolute structure parameter	0.028 (11)
Computer programs: CrystalClear SM-Expert (Rigaku, 2011 ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1036742

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617002875/sj4092sup1.cif

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

checkCIF report

Computing details top

Data collection: CrystalClear SM-Expert (Rigaku, 2011); cell refinement: 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).

(E)-1-(3-Bromophenyl)-3-(4-nitrophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀BrNO₃	F(000) = 332
M_r = 332.14	D_x = 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

Data collection top

Rigaku Saturn724+ diffractometer	2605 independent reflections
Radiation source: fine-focus sealed tube	2325 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
Detector resolution: 18.4 pixels mm^-1	θ_max = 26.1°, θ_min = 1.9°
profile data from ω–scans	h = −7→7
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	k = −6→6
T_min = 0.312, T_max = 0.751	l = −27→24
8418 measured reflections

Refinement top

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(F_o²) + (0.0421P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2605 reflections	Δρ_max = 0.59 e Å⁻³
181 parameters	Δρ_min = −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)

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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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