Crystal structure and Hirshfeld surface analysis of (2E)-1-(3-bromo­phen­yl)-3-(4-fluoro­phen­yl)prop-2-en-1-one

Atioğlu, Z.; Bindya, S.; Akkurt, M.; Chidan Kumar, C.S.

doi:10.1107/S2056989018018418

research communications

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 75| Part 2| February 2019| Pages 146-149

https://doi.org/10.1107/S2056989018018418

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Crystal structure and Hirshfeld surface analysis of (2E)-1-(3-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one

Zeliha Atioğlu,^a S. Bindya,^b Mehmet Akkurt ^c ^* and C. S. Chidan Kumar ^d

^aİlke Education and Health Foundation, Cappadocia University, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey, ^bDepartment of Chemistry, Sri Jayachamarajendra College of Engineering, JSS Science & Technology University, Mysore 570006, Karnataka, India, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570028, Karnataka, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 17 December 2018; accepted 28 December 2018; online 4 January 2019)

In the title compound, C₁₅H₁₀BrFO, the molecular structure consists of a 3-bromophenyl ring and a 4-fluorophenyl ring linked via a prop-2-en-1-one spacer. The 3-bromophenyl and 4-fluorophenyl rings make a dihedral angle of 48.90 (15)°. The molecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. In the crystal, molecules are linked by C—H⋯π interactions between the bromophenyl and fluorophenyl rings of molecules, resulting in a two-dimensional layered structure parallel to the ab plane. The molecular packing is stabilized by weak Br⋯H and F⋯H contacts, one of which is on the one side of each layer, and the second is on the other. The intermolecular interactions in the crystal packing were further analysed using Hirshfeld surface analysis, which indicates that the most significant contacts are Cl⋯H/H⋯Cl (20.8%), followed by C⋯H/H⋯C (31.1%), H⋯H (21.7%), Br⋯H/H⋯Br (14.2%), F⋯H/H⋯F (9.8%), O⋯H/H⋯O (9.7%).

Keywords: crystal structure; 3-bromophenyl ring; 4-fluorophenyl ring; a prop-2-en-1-one spacer; Hirshfeld surface analysis.

CCDC reference: 1036740

1. Chemical context

An aromatic ketone and an enone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones or chalconoids. Chalcones are 1,3-diphenyl-2-propene-1-one, in which two aromatic rings are linked by a three carbon α,β-unsaturated carbonyl system. The α,β-unsaturated ketone group in chalcones is responsible for their enzyme inhibitory activity including xanthine oxidase, aldose reductase, soluble epoxide hydrolase, protein tyrosine kinase, quinonone reductase and mono amine oxidase (Amita et al., 2014 ). Chalcones are abundant in nature starting from ferns to higher plants and a number of them are polyhydroxylated in the aryl rings. They are considered to be precursors of flavonoids and isoflavonoids. Chalcones possess conjugated double bonds and a completely delocalized π-electron system on both benzene rings. Molecules that possess such a system have relatively low redox potentials and have a greater probability of undergoing electron-transfer reactions. Crystal structures have been reported for 3-(3-bromophenyl)-1-(4-bromophenyl)prop-2-en-1-one (Teh et al., 2006 ), 3-(3-bromophenyl)-1-(2-naphthyl)prop-2-en-1-one (Moorthi et al., 2007 ), (E)-1-(3-bromophenyl)-3-(4-ethoxyphenyl)prop-2-en-1-one (Fun et al., 2008 ), (E)-3-(biphenyl-4-yl)-1-(3-bromophenyl)prop-2-en-1-one (Dutkiewicz et al., 2009 ), (2E)-1-(3-bromophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (Harrison et al., 2010 ), (2E)-1-(3-bromophenyl)-3-(4,5-dimethoxy-2-nitrophenyl)prop-2-en-1-one (Jasinski et al., 2010 ), (E)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Escobar et al., 2012 ), (E)-1-(3-bromophenyl)-3-(4-nitrophenyl)prop-2-en-1-one (Harini et al., 2017 ) and (E)-1-(3-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one (Rajendraprasad et al., 2017 ). We herewith report the crystal and molecular structure of the title compound.

2. Structural commentary

As shown in Fig. 1, the title compound is constructed from two aromatic rings (3-bromophenyl and 4-fluorophenyl rings), which are linked by a C=C—C(=O)—C enone bridge. Probably as a result of the steric repulsion between the fluoride and bromine atoms of adjacent molecules, the C5—C6—C7— O1 and O1—C7—C8—C9 torsion angles about the enone bridge are 25.1 (4) and 14.0 (5) °, respectively. Hence, the dihedral angle between the 3-bromophenyl ring and the 4-fluorophenyl ring increases to 48.90 (15)°. The molecular conformation of the title compound is stabilized by intramolecular C—H⋯Cl contacts (Table 1), producing S(6) and S(5) ring motifs. The bond lengths and angles are comparable with those found in the related compounds (2E)-3-(3-chlorophenyl)-1-(3,4-dimethoxyphenyl)-prop-2-en-1-one (Sheshadri et al., 2018a ), (2E)-3-(3-bromo-4-fluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (Sheshadri et al., 2018b ), (E)-3-(3,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2yl)prop-2-en-1-one (Ezhilarasi et al., 2015 ), (E)-1-(3-bromophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one (Escobar et al., 2012) and (E)-3-(2-bromophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one (Li et al., 2012 ).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the 3-bromophenyl (C1–C6) and 4-fluorophenyl (C10–C15) rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯Cg2ⁱ	0.93	2.93	3.571 (4)	127
C5—H5A⋯Cg2ⁱⁱ	0.93	2.98	3.642 (3)	129
C14—H14A⋯Cg1ⁱⁱⁱ	0.93	2.90	3.590 (3)	132
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y, -z+1; (iii) -x+1, -y, -z+1.

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, molecules are linked by C—H⋯π interactions between the bromophenyl and fluorophenyl rings of molecules, resulting in a two-dimensional layered structure parallel to the ab plane (Table 1; Fig. 2). The molecular packing is stabilized by weak Br⋯H and ⋯H contacts, one of which is on the one side of a layer, and the second is on the other. A summary of the short contacts is given in Table 2.

Table 2
Summary of short interatomic contacts (Å) in the title compound

Contact	Distance	Symmetry operation
Br1⋯Br1	3.7222 (6)	3 − x, 1 − y, −z
H3A⋯Br1	3.19	2 − x, 1 − y, −z
H12A⋯F1	2.66	1 − x, −y, 2 − z
H1A⋯O1	2.82	−1 + x, y, z
H11A⋯C3	3.01	2 − x, 1 − y, 1 − z
H14A⋯C6	2.95	1 − x, −y, 1 − z
H2A⋯C10	2.89	1 − x, 1 − y, 1 − z
H5A⋯C15	3.00	2 − x, −y, 1 − z

Figure 2
A view of the C—H⋯π interactions in the title compound.

Hirshfeld surfaces and fingerprint plots were generated for the title compound using CrystalExplorer (McKinnon et al., 2007 ). Hirshfeld surfaces enable the visualization of intermolecular interactions by different colours and colour intensity, representing short or long contacts and indicating the relative strength of the interactions.

The function d_norm is a ratio enclosing the distances of any surface point to the nearest interior (d_i) and exterior (d_e) atom and the van der Waals radii of the atoms (Hirshfeld, 1977 ; Soman et al., 2014 ). The function d_norm will be equal to zero when intermolecular distances are close to van der Waals contacts. They are indicated by a white colour on the Hirshfeld surface, while contacts longer than the sum of van der Waals radii with positive d_norm values are coloured in blue. The surface plot for d_norm (Fig. 3) was generated using a high standard surface resolution over a colour scale of −0.0186 to 1.3784 a.u.

Figure 3
A view of the Hirshfeld surface of the title compound mapped over d_norm, using a fixed colour scale of −0.0186 (red) to 1.3784 (blue) a.u.

The overall two-dimensional fingerprint plot for the title compound and those delineated into C⋯H/H⋯C, H⋯H, Br⋯H/H⋯Br, F⋯H/H⋯F and O⋯H/H⋯O contacts are illustrated in Fig. 4. The percentage contributions of the various interatomic contacts to the Hirshfeld surfaces are given in Table 3. The presence of C—H⋯π interactions in the crystal is indicated by the pair of characteristic wings in the fingerprint plot delineated into C⋯H/H⋯C contacts (31.1% contribution to the Hirshfeld surface). The C⋯H/H⋯C interactions are represented by the spikes at the bottom right and left (d_e + d_i ≃ 2.75 Å). H⋯H contacts are disfavoured when the number of H atoms on the molecular surface is large. The Br⋯H/H⋯Br and F⋯H/H⋯F contacts (Fig. 4) in the structure with 14.2 and 9.8% contributions, respectively, to the Hirshfeld surface are viewed as pairs of spikes with the tips at d_e + d_i ≃ 3.05 and 2.45 Å, respectively.

Table 3
Percentage contributions of interatomic contacts to the Hirshfeld surface for the compound

Contact	Percentage contribution
C⋯H/H⋯C	31.1
H⋯H	21.7
Br⋯H/H⋯Br	14.2
F⋯H/H⋯F	9.8
O⋯H/H⋯O	9.7
C⋯C	3.4
Br⋯F/F⋯Br	3.1
F⋯C/C⋯F	1.8
Br.·C/C⋯Br	1.5
C⋯O/O⋯C	1.5
F⋯F	1.3
Br⋯Br	0.9

Figure 4
The two-dimensional fingerprint plots of the title compound.

4. Synthesis and crystallization

The title compound was synthesized as per the procedure reported earlier (Kumar et al., 2013a ,b ). 1-(3-Bromophenyl)ethanone (0.01 mol) and 4-fluorobenzaldehyde (0.01 mol) were dissolved in 30 ml methanol. A catalytic amount of NaOH was added to the solution dropwise under vigorous stirring. The reaction mixture was stirred for about 4 h at room temperature. The formed crude products were filtered, washed successively with distilled water and recrystallized from methanol to obtain the title chalcone. The melting point (338–342 K) was determined using a Stuart Scientific (UK) apparatus.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 4. H atoms were positioned geometrically and refined using riding model, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C). Owing to poor agreement between observed and calculated intensities, thirteen outliers ( $[\overline{1}]$ 15, 131, $[\overline{3}]$ 26, 043, 254, $[\overline{1}]$ 23, $[\overline{2}]$ 28, 150, 253, $[\overline{1}]$ 11, $[\overline{3}]$ 25, 543, 623) were omitted in the final cycles of refinement.

Table 4
Experimental details

Crystal data
Chemical formula	C₁₅H₁₀BrFO
M_r	305.14
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	294
a, b, c (Å)	5.9255 (6), 7.5867 (8), 14.1427 (15)
α, β, γ (°)	89.774 (2), 82.671 (2), 87.712 (2)
V (Å³)	630.09 (11)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	3.26
Crystal size (mm)	0.30 × 0.28 × 0.26

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007 )
T_min, T_max	0.398, 0.431
No. of measured, independent and observed [I > 2σ(I)] reflections	9618, 2442, 2101
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.10
No. of reflections	2442
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.40
Computer programs: APEX2 and SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1036740

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018018418/xu5955sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018018418/xu5955Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018018418/xu5955Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

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

Crystal data top

C₁₅H₁₀BrFO	Z = 2
M_r = 305.14	F(000) = 304
Triclinic, P1	D_x = 1.608 Mg m⁻³
a = 5.9255 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.5867 (8) Å	Cell parameters from 4763 reflections
c = 14.1427 (15) Å	θ = 3.6–27.3°
α = 89.774 (2)°	µ = 3.26 mm⁻¹
β = 82.671 (2)°	T = 294 K
γ = 87.712 (2)°	Block, colourless
V = 630.09 (11) Å³	0.30 × 0.28 × 0.26 mm

Data collection top

Bruker APEXII CCD diffractometer	2101 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 26.0°, θ_min = 1.5°
T_min = 0.398, T_max = 0.431	h = −7→7
9618 measured reflections	k = −7→9
2442 independent reflections	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0481P)² + 0.4984P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
2442 reflections	Δρ_max = 0.76 e Å⁻³
163 parameters	Δρ_min = −0.40 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Br1	1.29286 (6)	0.37541 (6)	0.08193 (2)	0.06864 (18)
F1	0.2394 (4)	−0.0245 (4)	0.91227 (16)	0.0855 (7)
O1	1.2246 (4)	0.2758 (4)	0.46700 (17)	0.0609 (6)
C1	0.7494 (5)	0.4234 (4)	0.3499 (2)	0.0485 (7)
H1A	0.639101	0.432526	0.402871	0.058*
C2	0.7020 (5)	0.4863 (5)	0.2621 (3)	0.0553 (8)
H2A	0.560236	0.540073	0.257032	0.066*
C3	0.8602 (5)	0.4709 (4)	0.1826 (2)	0.0530 (8)
H3A	0.825976	0.511138	0.123703	0.064*
C4	1.0720 (5)	0.3940 (4)	0.1920 (2)	0.0440 (6)
C5	1.1280 (5)	0.3320 (4)	0.2783 (2)	0.0408 (6)
H5A	1.271938	0.281871	0.283008	0.049*
C6	0.9640 (5)	0.3463 (4)	0.3583 (2)	0.0401 (6)
C7	1.0259 (5)	0.2821 (4)	0.4522 (2)	0.0453 (7)
C8	0.8399 (5)	0.2254 (4)	0.5237 (2)	0.0491 (7)
H8A	0.697720	0.207874	0.504874	0.059*
C9	0.8697 (5)	0.1987 (4)	0.6141 (2)	0.0437 (6)
H9A	1.012966	0.220989	0.630447	0.052*
C10	0.7013 (5)	0.1380 (4)	0.6910 (2)	0.0402 (6)
C11	0.7434 (5)	0.1542 (4)	0.7850 (2)	0.0479 (7)
H11A	0.878507	0.202032	0.797670	0.058*
C12	0.5888 (6)	0.1008 (5)	0.8598 (2)	0.0585 (8)
H12A	0.617731	0.112494	0.922560	0.070*
C13	0.3923 (6)	0.0304 (5)	0.8394 (2)	0.0550 (8)
C14	0.3445 (5)	0.0080 (4)	0.7482 (2)	0.0500 (7)
H14A	0.211180	−0.044035	0.736707	0.060*
C15	0.4981 (5)	0.0640 (4)	0.6738 (2)	0.0456 (7)
H15A	0.466180	0.052442	0.611505	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0651 (3)	0.0932 (3)	0.0443 (2)	0.00443 (19)	0.00298 (15)	0.01381 (18)
F1	0.0780 (15)	0.117 (2)	0.0573 (13)	−0.0210 (14)	0.0140 (11)	0.0172 (13)
O1	0.0431 (12)	0.0916 (19)	0.0486 (13)	−0.0062 (12)	−0.0076 (9)	0.0087 (12)
C1	0.0376 (14)	0.0507 (18)	0.0559 (18)	−0.0022 (13)	−0.0009 (13)	−0.0040 (14)
C2	0.0405 (15)	0.0551 (19)	0.072 (2)	0.0047 (14)	−0.0157 (15)	0.0050 (16)
C3	0.0502 (17)	0.0548 (19)	0.0564 (19)	−0.0041 (14)	−0.0162 (14)	0.0139 (15)
C4	0.0426 (14)	0.0470 (16)	0.0416 (15)	−0.0025 (13)	−0.0023 (12)	0.0043 (12)
C5	0.0359 (13)	0.0421 (15)	0.0444 (15)	−0.0014 (12)	−0.0049 (11)	0.0028 (12)
C6	0.0368 (13)	0.0397 (15)	0.0442 (15)	−0.0062 (11)	−0.0052 (11)	−0.0003 (12)
C7	0.0435 (15)	0.0490 (17)	0.0440 (15)	−0.0073 (13)	−0.0059 (12)	−0.0013 (13)
C8	0.0437 (15)	0.0570 (19)	0.0474 (17)	−0.0093 (14)	−0.0067 (13)	0.0011 (14)
C9	0.0398 (14)	0.0441 (16)	0.0468 (16)	−0.0008 (12)	−0.0048 (12)	0.0003 (13)
C10	0.0418 (14)	0.0342 (14)	0.0445 (15)	0.0027 (11)	−0.0062 (12)	0.0009 (12)
C11	0.0460 (16)	0.0496 (17)	0.0495 (17)	−0.0009 (13)	−0.0117 (13)	0.0032 (13)
C12	0.065 (2)	0.071 (2)	0.0397 (16)	−0.0030 (17)	−0.0085 (14)	0.0045 (15)
C13	0.0530 (18)	0.060 (2)	0.0490 (18)	0.0006 (15)	0.0050 (14)	0.0107 (15)
C14	0.0425 (15)	0.0476 (17)	0.0597 (19)	−0.0055 (13)	−0.0049 (13)	0.0022 (14)
C15	0.0478 (16)	0.0470 (17)	0.0424 (15)	−0.0023 (13)	−0.0071 (12)	−0.0008 (13)

Geometric parameters (Å, º) top

Br1—C4	1.903 (3)	C8—C9	1.327 (4)
F1—C13	1.358 (4)	C8—H8A	0.9300
O1—C7	1.221 (4)	C9—C10	1.465 (4)
C1—C2	1.387 (5)	C9—H9A	0.9300
C1—C6	1.397 (4)	C10—C11	1.390 (4)
C1—H1A	0.9300	C10—C15	1.398 (4)
C2—C3	1.371 (5)	C11—C12	1.379 (5)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.384 (4)	C12—C13	1.364 (5)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.382 (4)	C13—C14	1.368 (5)
C5—C6	1.396 (4)	C14—C15	1.378 (4)
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.496 (4)	C15—H15A	0.9300
C7—C8	1.474 (4)

C2—C1—C6	119.6 (3)	C7—C8—H8A	119.1
C2—C1—H1A	120.2	C8—C9—C10	127.1 (3)
C6—C1—H1A	120.2	C8—C9—H9A	116.5
C3—C2—C1	121.2 (3)	C10—C9—H9A	116.5
C3—C2—H2A	119.4	C11—C10—C15	118.2 (3)
C1—C2—H2A	119.4	C11—C10—C9	119.2 (3)
C2—C3—C4	118.6 (3)	C15—C10—C9	122.5 (3)
C2—C3—H3A	120.7	C12—C11—C10	121.3 (3)
C4—C3—H3A	120.7	C12—C11—H11A	119.3
C5—C4—C3	122.2 (3)	C10—C11—H11A	119.3
C5—C4—Br1	119.3 (2)	C13—C12—C11	118.3 (3)
C3—C4—Br1	118.5 (2)	C13—C12—H12A	120.9
C4—C5—C6	118.6 (3)	C11—C12—H12A	120.9
C4—C5—H5A	120.7	F1—C13—C12	119.0 (3)
C6—C5—H5A	120.7	F1—C13—C14	118.2 (3)
C5—C6—C1	119.8 (3)	C12—C13—C14	122.8 (3)
C5—C6—C7	118.6 (3)	C13—C14—C15	118.6 (3)
C1—C6—C7	121.5 (3)	C13—C14—H14A	120.7
O1—C7—C8	122.3 (3)	C15—C14—H14A	120.7
O1—C7—C6	120.2 (3)	C14—C15—C10	120.7 (3)
C8—C7—C6	117.5 (2)	C14—C15—H15A	119.6
C9—C8—C7	121.9 (3)	C10—C15—H15A	119.6
C9—C8—H8A	119.1

C6—C1—C2—C3	1.5 (5)	C6—C7—C8—C9	−166.9 (3)
C1—C2—C3—C4	−1.4 (5)	C7—C8—C9—C10	−178.2 (3)
C2—C3—C4—C5	0.3 (5)	C8—C9—C10—C11	−165.8 (3)
C2—C3—C4—Br1	−179.2 (3)	C8—C9—C10—C15	14.1 (5)
C3—C4—C5—C6	0.7 (5)	C15—C10—C11—C12	−0.7 (5)
Br1—C4—C5—C6	−179.9 (2)	C9—C10—C11—C12	179.2 (3)
C4—C5—C6—C1	−0.6 (4)	C10—C11—C12—C13	0.3 (5)
C4—C5—C6—C7	−179.0 (3)	C11—C12—C13—F1	179.3 (3)
C2—C1—C6—C5	−0.5 (4)	C11—C12—C13—C14	1.2 (6)
C2—C1—C6—C7	177.9 (3)	F1—C13—C14—C15	179.7 (3)
C5—C6—C7—O1	25.1 (4)	C12—C13—C14—C15	−2.1 (5)
C1—C6—C7—O1	−153.3 (3)	C13—C14—C15—C10	1.7 (5)
C5—C6—C7—C8	−154.0 (3)	C11—C10—C15—C14	−0.3 (5)
C1—C6—C7—C8	27.6 (4)	C9—C10—C15—C14	179.8 (3)
O1—C7—C8—C9	14.0 (5)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the 3-bromophenyl (C1–C6) and 4-fluorophenyl (C10–C15) rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1	0.93	2.53	2.840 (4)	100
C2—H2A···Cg2ⁱ	0.93	2.93	3.571 (4)	127
C5—H5A···Cg2ⁱⁱ	0.93	2.98	3.642 (3)	129
C14—H14A···Cg1ⁱⁱⁱ	0.93	2.90	3.590 (3)	132

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y, −z+1; (iii) −x+1, −y, −z+1.

Summary of short interatomic contacts (Å) in the title compound top

Contact	Distance	Symmetry operation
Br1···Br1	3.7222 (6)	3 - x, 1 - y, -z
H3A···Br1	3.19	2 - x, 1 - y, -z
H12A···F1	2.66	1 - x, -y, 2 - z
H1A···O1	2.82	-1 + x, y, z
H11A···C3	3.01	2 - x, 1 - y, 1 - z
H14A···C6	2.95	1 - x, -y, 1 - z
H2A···C10	2.89	1 - x, 1 - y, 1 - z
H5A···C15	3.00	2 - x, -y, 1 - z

Percentage contributions of interatomic contacts to the Hirshfeld surface for the compound top

Contact	Percentage contribution
C···H/H···C	31.1
H···H	21.7
Br···H/H···Br	14.2
F···H/H···F	9.8
O···H/H···O	9.7
C···C	3.4
Br···F/F···Br	3.1
F···C/C···F	1.8
Br..C/C···Br	1.5
C···O/O···C	1.5
F···F	1.3
Br···Br	0.9

Acknowledgements

The authors extend their appreciation to the Vidya Vikas Research & Development Centre for the facilities and encouragement.

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