(E)-1-(3-Bromo­phen­yl)-3-(3-fluoro­phen­yl)prop-2-en-1-one

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

doi:10.1107/S2414314617003790

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 3| March 2017| x170379

https://doi.org/10.1107/S2414314617003790

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(E)-1-(3-Bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one

S. Rajendraprasad,^a C. S. Chidan Kumar,^b Ching Kheng Quah,^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, ^bDepartment of Engineering Chemistry, Vidya Vikas Institute of Engineering and Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570 028, India, ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800 USM, Malaysia, ^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: naveen@ioe.uni-mysore.ac.in, khalil.i@najah.edu

Edited by J. Simpson, University of Otago, New Zealand (Received 7 March 2017; accepted 9 March 2017; online 14 March 2017)

In the title compound, C₁₅H₁₀BrFO, the olefinic double bond adopts an E conformation. The molecule is non-planar as seen by the dihedral angle of 48.92 (11)° between the bromophenyl and fluorophenyl rings. The carbonyl group is twisted from the plane of the bromophenyl ring and the olefinic double bond. The trans conformation of the C=C double bond in the central enone group is confirmed by the C—C=C—C torsion angle of −165.7 (2)°.

Keywords: crystal structure; chalcone; E configuration.

CCDC reference: 1536989

Structure description

Great attention has been paid in recent years to the development of materials, including chalcone derivatives, for second and third order non-linear optical (NLO) applications such as telecommunications, optical computing, optical data storage and optical information processing (Shettigar et al., 2006 ). Chalcones and their derivatives also demonstrate a wide range of biological activities including applications as antioxidants, antifungal, antibacterial and cardioprotective agents. In view of the broad spectrum of applications associated with chalcones and as a part of our ongoing work on such molecules (Chidan et al., 2017 ; Harini et al., 2017 ), we report the synthesis and crystal structure of the title compound here.

The molecule, shown in Fig. 1, is non-planar. This is evident from the dihedral angle of 48.92 (11)° between the bromophenyl and fluorophenyl rings that are bridged by the carbonyl substituent on the bromobenzene ring and olefinic double bond. This is higher than the value of 19.13 (15)° reported for the related chalcone derivative (E)-3-(2,3-dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (Naveen et al., 2016 ). The trans conformation about the C7=C8 double bond in the central enone group is confirmed by a C6—C7=C8—C9 torsion angle, −165.7 (2)°. The carbonyl group at C7 is twisted from the plane of the bromophenyl ring and the olefinic double bond, as indicated by the O1—C7—C6—C5 and O1—C7—C8—C9 torsion angles of 25.4 (3) and 14.5 (4)°, respectively. No classical hydrogen bonds were found in the structure.

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.

Synthesis and crystallization

3′-Bromoacetophenone (1.99 g, 0.01 mol) was mixed with 3-fluorobenzaldehyde (1.24 g, 0.01 mol) and dissolved in methanol (20 ml). To this solution, 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 several times with distilled water and finally recrystallized from methanol to give the pure chalcone. Single crystals suitable for X-ray diffraction studies were grown by the slow evaporation of the methanol solution. Yield 88%, m.p. 311–313 K.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrFO
M_r	305.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.6032 (7), 5.9277 (6), 27.600 (3)
β (°)	93.183 (2)
V (Å³)	1242.0 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.31
Crystal size (mm)	0.49 × 0.44 × 0.33

Data collection
Diffractometer	Rigaku Saturn724+
Absorption correction	Multi-scan (NUMABS; Rigaku, 1999 )
T_min, T_max	0.293, 0.408
No. of measured, independent and observed [I > 2σ(I)] reflections	11350, 2983, 2228
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.662

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.02
No. of reflections	2983
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.26
Computer programs: CrystalClear SM-Expert (Rigaku, 2011 ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1536989

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617003790/sj4095sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617003790/sj4095Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617003790/sj4095Isup3.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-(3-fluorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₁₀BrFO	F(000) = 608
M_r = 305.13	D_x = 1.632 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2228 reflections
a = 7.6032 (7) Å	θ = 1.5–28.1°
b = 5.9277 (6) Å	µ = 3.31 mm⁻¹
c = 27.600 (3) Å	T = 100 K
β = 93.183 (2)°	Prism, green
V = 1242.0 (2) Å³	0.49 × 0.44 × 0.33 mm
Z = 4

Data collection top

Rigaku Saturn724+ diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	2228 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 18.4 pixels mm^-1	θ_max = 28.1°, θ_min = 1.5°
profile data from ω–scans	h = −10→9
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	k = −7→7
T_min = 0.293, T_max = 0.408	l = −33→36
11350 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0526P)² + 0.0964P] where P = (F_o² + 2F_c²)/3
2983 reflections	(Δ/σ)_max = 0.002
163 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

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	0.69112 (4)	0.31515 (5)	0.70851 (1)	0.0627 (1)
F1	0.8178 (3)	0.7659 (3)	0.26863 (6)	0.0852 (7)
O1	0.7328 (3)	0.2879 (3)	0.51261 (6)	0.0620 (7)
C1	0.6003 (3)	0.7850 (4)	0.57483 (9)	0.0475 (7)
C2	0.5495 (3)	0.8515 (4)	0.62018 (10)	0.0515 (8)
C3	0.5749 (3)	0.7133 (4)	0.65974 (9)	0.0483 (8)
C4	0.6523 (3)	0.5051 (4)	0.65369 (8)	0.0421 (7)
C5	0.7009 (3)	0.4319 (3)	0.60926 (7)	0.0397 (6)
C6	0.6757 (3)	0.5727 (3)	0.56913 (7)	0.0401 (6)
C7	0.7279 (3)	0.4895 (4)	0.52096 (8)	0.0454 (7)
C8	0.7732 (3)	0.6600 (4)	0.48446 (9)	0.0501 (8)
C9	0.7850 (3)	0.6067 (4)	0.43836 (8)	0.0450 (7)
C10	0.8346 (3)	0.7597 (3)	0.39956 (8)	0.0388 (6)
C11	0.8041 (3)	0.6932 (4)	0.35145 (9)	0.0464 (7)
C12	0.8471 (4)	0.8349 (4)	0.31528 (9)	0.0543 (8)
C13	0.9198 (3)	1.0431 (4)	0.32362 (9)	0.0531 (8)
C14	0.9527 (3)	1.1078 (4)	0.37117 (9)	0.0496 (8)
C15	0.9101 (3)	0.9698 (4)	0.40878 (8)	0.0444 (7)
H1A	0.58430	0.88140	0.54840	0.0570*
H2A	0.49730	0.99200	0.62380	0.0620*
H3A	0.54090	0.75890	0.69010	0.0580*
H5A	0.75030	0.28960	0.60600	0.0480*
H8A	0.79380	0.80820	0.49430	0.0600*
H9A	0.75960	0.45830	0.42960	0.0540*
H11A	0.75480	0.55290	0.34410	0.0560*
H13A	0.94610	1.13760	0.29810	0.0640*
H14A	1.00470	1.24710	0.37800	0.0600*
H15A	0.93200	1.01750	0.44060	0.0530*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0882 (2)	0.0625 (2)	0.0379 (2)	0.0103 (1)	0.0080 (1)	0.0039 (1)
F1	0.1197 (15)	0.0972 (12)	0.0388 (9)	−0.0197 (11)	0.0048 (9)	−0.0105 (8)
O1	0.1000 (15)	0.0422 (10)	0.0446 (9)	−0.0032 (9)	0.0101 (9)	−0.0015 (7)
C1	0.0502 (13)	0.0354 (11)	0.0561 (14)	−0.0029 (9)	−0.0038 (11)	0.0059 (10)
C2	0.0502 (13)	0.0378 (12)	0.0666 (16)	0.0026 (9)	0.0039 (11)	−0.0067 (11)
C3	0.0496 (13)	0.0427 (12)	0.0532 (14)	−0.0005 (10)	0.0078 (11)	−0.0111 (10)
C4	0.0469 (12)	0.0404 (11)	0.0392 (11)	−0.0030 (9)	0.0046 (9)	−0.0007 (9)
C5	0.0438 (11)	0.0329 (10)	0.0425 (11)	−0.0028 (9)	0.0032 (9)	−0.0019 (9)
C6	0.0426 (11)	0.0365 (11)	0.0411 (11)	−0.0060 (9)	0.0015 (9)	−0.0003 (9)
C7	0.0536 (13)	0.0435 (12)	0.0387 (11)	−0.0074 (10)	−0.0003 (9)	0.0005 (9)
C8	0.0648 (15)	0.0413 (12)	0.0440 (12)	−0.0101 (10)	0.0027 (11)	−0.0017 (9)
C9	0.0506 (12)	0.0371 (10)	0.0474 (12)	−0.0017 (9)	0.0036 (10)	0.0004 (9)
C10	0.0387 (11)	0.0372 (10)	0.0408 (11)	0.0017 (8)	0.0057 (9)	0.0007 (8)
C11	0.0508 (13)	0.0421 (12)	0.0465 (12)	−0.0040 (9)	0.0043 (10)	−0.0073 (10)
C12	0.0595 (15)	0.0663 (16)	0.0374 (12)	0.0028 (12)	0.0052 (10)	−0.0035 (11)
C13	0.0565 (14)	0.0565 (14)	0.0471 (13)	−0.0029 (11)	0.0097 (10)	0.0089 (11)
C14	0.0492 (13)	0.0431 (12)	0.0566 (14)	−0.0088 (10)	0.0046 (11)	0.0002 (11)
C15	0.0494 (12)	0.0430 (11)	0.0408 (11)	−0.0034 (9)	0.0018 (9)	−0.0050 (9)

Geometric parameters (Å, º) top

Br1—C4	1.896 (2)	C11—C12	1.358 (3)
F1—C12	1.358 (3)	C12—C13	1.367 (3)
O1—C7	1.218 (3)	C13—C14	1.377 (3)
C1—C2	1.387 (4)	C14—C15	1.374 (3)
C1—C6	1.395 (3)	C1—H1A	0.9300
C2—C3	1.370 (4)	C2—H2A	0.9300
C3—C4	1.381 (3)	C3—H3A	0.9300
C4—C5	1.371 (3)	C5—H5A	0.9300
C5—C6	1.392 (3)	C8—H8A	0.9300
C6—C7	1.492 (3)	C9—H9A	0.9300
C7—C8	1.481 (3)	C11—H11A	0.9300
C8—C9	1.319 (3)	C13—H13A	0.9300
C9—C10	1.469 (3)	C14—H14A	0.9300
C10—C11	1.392 (3)	C15—H15A	0.9300
C10—C15	1.389 (3)

C2—C1—C6	119.7 (2)	C13—C14—C15	121.1 (2)
C1—C2—C3	121.0 (2)	C10—C15—C14	120.5 (2)
C2—C3—C4	118.7 (2)	C2—C1—H1A	120.00
Br1—C4—C3	118.86 (17)	C6—C1—H1A	120.00
Br1—C4—C5	119.22 (17)	C1—C2—H2A	120.00
C3—C4—C5	121.9 (2)	C3—C2—H2A	119.00
C4—C5—C6	119.35 (18)	C2—C3—H3A	121.00
C1—C6—C5	119.37 (19)	C4—C3—H3A	121.00
C1—C6—C7	121.99 (19)	C4—C5—H5A	120.00
C5—C6—C7	118.63 (18)	C6—C5—H5A	120.00
O1—C7—C6	120.4 (2)	C7—C8—H8A	119.00
O1—C7—C8	122.0 (2)	C9—C8—H8A	119.00
C6—C7—C8	117.64 (19)	C8—C9—H9A	117.00
C7—C8—C9	121.6 (2)	C10—C9—H9A	117.00
C8—C9—C10	126.1 (2)	C10—C11—H11A	120.00
C9—C10—C11	119.00 (19)	C12—C11—H11A	120.00
C9—C10—C15	122.7 (2)	C12—C13—H13A	121.00
C11—C10—C15	118.3 (2)	C14—C13—H13A	121.00
C10—C11—C12	119.5 (2)	C13—C14—H14A	120.00
F1—C12—C11	118.5 (2)	C15—C14—H14A	119.00
F1—C12—C13	118.4 (2)	C10—C15—H15A	120.00
C11—C12—C13	123.1 (2)	C14—C15—H15A	120.00
C12—C13—C14	117.6 (2)

C6—C1—C2—C3	1.1 (4)	C6—C7—C8—C9	−165.7 (2)
C2—C1—C6—C5	−0.8 (3)	C7—C8—C9—C10	−177.8 (2)
C2—C1—C6—C7	178.1 (2)	C8—C9—C10—C11	−166.0 (2)
C1—C2—C3—C4	−0.1 (4)	C8—C9—C10—C15	13.6 (4)
C2—C3—C4—Br1	179.02 (18)	C9—C10—C11—C12	179.0 (2)
C2—C3—C4—C5	−1.3 (4)	C15—C10—C11—C12	−0.6 (3)
Br1—C4—C5—C6	−178.77 (17)	C9—C10—C15—C14	−179.4 (2)
C3—C4—C5—C6	1.5 (3)	C11—C10—C15—C14	0.2 (3)
C4—C5—C6—C1	−0.5 (3)	C10—C11—C12—F1	179.4 (2)
C4—C5—C6—C7	−179.5 (2)	C10—C11—C12—C13	−0.1 (4)
C1—C6—C7—O1	−153.6 (2)	F1—C12—C13—C14	−178.4 (2)
C1—C6—C7—C8	26.6 (3)	C11—C12—C13—C14	1.1 (4)
C5—C6—C7—O1	25.4 (3)	C12—C13—C14—C15	−1.5 (4)
C5—C6—C7—C8	−154.4 (2)	C13—C14—C15—C10	0.8 (4)
O1—C7—C8—C9	14.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.52	2.832 (3)	100

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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