Crystal structure and Hirshfeld surface analysis of a bromo­chalcone: (E)-1-(3-bromo­phen­yl)-3-(2,6-di­chloro­phen­yl)prop-2-en-1-one

Bindya, S.; Chidan Kumar, C.S.; Naveen, S.; Siddaraju, B.P.; Quah, C.K.; Raihan, M.A.

doi:10.1107/S205698901900104X

research communications

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ISSN: 2056-9890

Volume 75| Part 2| February 2019| Pages 264-267

https://doi.org/10.1107/S205698901900104X

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Crystal structure and Hirshfeld surface analysis of a bromochalcone: (E)-1-(3-bromophenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one

S. Bindya,^a C. S. Chidan Kumar,^b S. Naveen,^c ^* B. P. Siddaraju,^d Ching Kheng Quah ^e and Md. Abu Raihan ^f ^*

^aDepartment of Chemistry, Sri Jayachamarajendra College of Engineering, JSS Science and Technology University, Mysuru 570 006, Karnataka, India, ^bDepartment of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahally, Mysuru 570 028, India, ^cDepartment of Physics, School of Engineering and Technology, Jain University, Bangalore 562 112, India, ^dDepartment of Chemistry, Cauvery Institute of Technology, Mandya 571 402, Karnataka, India, ^eX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^fHead of TVE Department, Islamic University of Technology (IUT), Gazipur 1704, Bangladesh
^*Correspondence e-mail: s.naveen@jainuniversity.ac.in, maraihan@iut-dhaka.edu

Edited by P. McArdle, National University of Ireland, Ireland (Received 17 January 2019; accepted 21 January 2019; online 25 January 2019)

In the title chalcone derivative, C₁₅H₉BrCl₂O, the aryl rings are inclined to each by 14.49 (17)°, and the configuration about the C=C bond is E. There is a short intramolecular C—H⋯Cl contact present resulting in the formation of an S(6) ring motif. In the crystal, the shortest intermolecular contacts are Cl⋯O contacts [3.173 (3) Å] that link the molecules to form a 2₁ helix propagating along the b-axis direction. The helices stack up the short crystallographic a axis, and are linked by offset π–π interactions [intercentroid distance = 3.983 (1) Å], forming layers lying parallel to the ab plane. A quantification of the intermolecular contacts in the crystal were estimated using Hirshfeld surface analysis and two-dimensional fingerprint plots.

Keywords: crystal structure; chalcone; enone bridge; E configuration; Cl⋯O contact; offset π–π interactions; Hirshfeld surface analysis; fingerprint plots.

CCDC reference: 1036741

1. Chemical context

Chalcones, considered to be the precursors of flavonoids and isoflavonoids, are abundant in edible plants. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon, α-unsaturated carbonyl system and are described by the generic term `chalcone'. Chalcones are coloured compounds because of the presence of the –CO—CH=CH– chromophore, which depends on the presence of other auxochromes. Chalcones are finding applications as organic non-linear optical materials (NLO) because of their good SHG conversion efficiencies (Chandra Shekhara Shetty et al., 2016 ; Raghavendra et al., 2017 ). In view of this interest we have synthesized the title chalcone derivative and report herein on its crystal structure and Hirshfeld surface analysis.

2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. It comprises two aromatic rings (2,6-dichlorophenyl and 3-bromophenyl) linked by the C7=C8—C9(=O1)—C10 enone bridge. The bond lengths and bond angles are normal and the molecular conformation is characterized by a dihedral angle of 14.49 (17)° between the mean planes of the two aromatic rings. The olefinic double bond [C7=C8 = 1.286 (5) Å] is in an E configuration. There is a short intramolecular C—H⋯Cl contact present resulting in the formation of an S(6) ring motif (Fig. 1 and Table 1). The unsaturated keto group is in a syn-periplanar conformation with respect to the olefinic double bond, which is evident from the O1—C9—C8—C7 torsion angle of 10.9 (6)°. The trans conformation of the C=C double bond in the central enone group is confirmed by the C6—C7—C8=C9 torsion angle of −179.8 (3)°. The bond angles O1—C9—C10 [120.4 (3)°], O1—C9—C8 [119.9 (3)°] and C9—C8—C7 [123.9 (4)°] about C9 indicate that this carbon atom is in a distorted trigonal–planar conformation.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Cl1	0.93	2.54	3.128 (4)	122

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. The intramolecular C—H⋯Cl hydrogen bond (Table 1

) is shown as a dashed line.

3. Supramolecular features

In the crystal, the molecules stack along the short crystallographic a axis. The shortest intermolecular contacts are Cl⋯O1ⁱ contacts [3.173 (3) Å; symmetry code (i): −x + 2, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ] that link the molecules to form 2₁ helices propagating along the b-axis direction (Fig. 2). The helices are linked by offset π–π interactions, forming undulating layers lying parallel to the ab plane, see Fig. 3 [Cg1⋯Cg1ⁱⁱ = 3.983 (2) Å, α = 0.0 (2)°, β = 24.7°, interplanar distance = 3.6193 (14) Å, offset 1.66 Å; Cg2⋯Cg2ⁱⁱⁱ = 3.984 (2) Å, α = 0.0 (2) °, β = 24.8 °, offset = 1.67 Å; Cg1 and Cg2 are the centroids of C1–C6 and C10–C15 rings, respectively; symmetry codes: (ii) x − 1, y, z; (iii) x + 1, y, z].

Figure 2
A partial view along the c axis of the crystal packing of the title compound. The intermolecular Cl⋯O interactions are shown as dashed lines.

Figure 3
A view along the a axis of the crystal packing of the title compound. The intermolecular Cl⋯O interactions are shown as dashed lines.

4. Hirshfeld surface analysis

Hirshfeld surfaces and fingerprint plots were generated for the title compound using CrystalExplorer (Wolff et al., 2012 ). 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. Fig. 4a shows the Hirshfeld surfaces mapped over d_norm, while Fig. 4b shows the Hirshfeld surfaces mapped over curvedness. In Fig. 4a, the red spots near atoms Cl1 and O1 result from the Cl⋯O interactions, which play a significant role in the molecular packing of the title compound (Figs. 2 and 3), and the Cl⋯H/H⋯Cl and O⋯H/H⋯O contacts. The curvedness plot (Fig. 4b) shows an extensive flat surface characteristic of planar stacking – see the Supramolecular features section above.

Figure 4
A view of the three-dimensional Hirshfeld surface of the title compound mapped over (a) d_norm and (b) curvedness.

The overall two-dimensional fingerprint plot (McKinnon et al., 2007 ), for the title compound and those delineated into Cl⋯H/H⋯Cl, H⋯H, C⋯C, Br⋯H/H⋯Br, C⋯H/H⋯C, O⋯H/H⋯O contacts are illustrated in Fig. 5; the most significant contributions from the different interatomic contacts to the Hirshfeld surfaces are as follows: Cl⋯H (23.6%), H⋯H (19.2%), C⋯C (14.8%), Br⋯H (14.2%), C⋯H (12%) and O⋯H (8%). Other intermolecular contacts contribute less than 5% to the Hirshfeld surface mapping. Interestingly, the Cl⋯O interactions (Fig. 2) make a contribution of only 2.2% to the Hirshfeld surface.

Figure 5
Two-dimensional fingerprint plots of the title compound showing the percentage contributions of all interactions, and the most significant individual types of interactions.

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 5.40, last update November 2018; Groom et al., 2016 ) using 1-(3-bromophenyl)-3-phenylprop-2-en-1-one as the main skeleton revealed the presence of 12 structures (see supporting information), including 1-(3-bromophenyl)-3-phenylprop-2-en-1-one itself (CSD refcode CICLUW; Rosli et al., 2007 ). The other structures closest to the title compound with a second halogen-substituted phenyl ring are: 1-(3-bromophenyl)-3-(4-chlorophenyl)prop-2-en-1-one (VIDFEU; Teh et al., 2007 ), 1-(3-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one (GASBEK; Rajendraprasad et al., 2017 ), and 1-(3-bromophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (OBIYUW; Ekbote et al., 2017 ). In these four compounds, the two benzene rings are inclined to each other by ca 49.93, 46.71, 48.92 and 47.74°, respectively. The same dihedral angle in the title compound is only 14.49 (17)° because of the presence of the intramolecular C—H⋯Cl hydrogen bond, as shown in Fig. 1 (Table 1).

6. Synthesis and crystallization

The title compound was synthesized according to a reported procedure (Chidan Kumar et al., 2014 ). 1-(3-Bromophenyl)ethanone (0.01 mol) and 2,6-dichlorobenzaldehyde (0.01 mol) were dissolved in 20 ml of methanol. A catalytic amount of NaOH was added dropwise with vigorous stirring. The reaction mixture was stirred for about 3 h at room temperature. The crude product was filtered, washed several times with distilled water and recrystallized from methanol. On slow evaporation of the solvent, colourless plate-like crystals of the title compound were obtained (m.p. 327–330 K).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were positioned geometrically (C—H = 0.95 Å) and refined using a riding model with U_iso(H) = 1.2U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₉BrCl₂O
M_r	356.02
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	294
a, b, c (Å)	3.9834 (7), 13.471 (2), 25.661 (4)
β (°)	92.736 (4)
V (Å³)	1375.4 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.36
Crystal size (mm)	0.47 × 0.14 × 0.05

Data collection
Diffractometer	Bruker APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.303, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	10857, 3242, 2260
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.657

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.124, 1.04
No. of reflections	3242
No. of parameters	172
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.33
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1036741

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S205698901900104X/qm2132sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901900104X/qm2132Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698901900104X/qm2132Isup3.cml

Details of CSD search. DOI: https://doi.org/10.1107/S205698901900104X/qm2132sup4.pdf

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); 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: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

(E)-1-(3-bromophenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one top

Crystal data top

C₁₅H₉BrCl₂O	F(000) = 704
M_r = 356.02	D_x = 1.719 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2260 reflections
a = 3.9834 (7) Å	θ = 1.6–27.8°
b = 13.471 (2) Å	µ = 3.36 mm⁻¹
c = 25.661 (4) Å	T = 294 K
β = 92.736 (4)°	Plate, colourless
V = 1375.4 (4) Å³	0.47 × 0.14 × 0.05 mm
Z = 4

Data collection top

Bruker APEXII DUO CCD area-detector diffractometer	3242 independent reflections
Radiation source: Rotating Anode	2260 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
Detector resolution: 18.4 pixels mm^-1	θ_max = 27.8°, θ_min = 1.6°
φ and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −17→15
T_min = 0.303, T_max = 0.842	l = −31→33
10857 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0691P)²] where P = (F_o² + 2F_c²)/3
3242 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.33 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	0.05103 (10)	0.56559 (3)	0.06384 (1)	0.0533 (2)
Cl1	1.1724 (3)	0.85319 (6)	0.33444 (4)	0.0585 (3)
Cl2	1.1077 (3)	0.48639 (7)	0.42380 (4)	0.0629 (4)
O1	0.6757 (10)	0.5127 (2)	0.25232 (11)	0.0795 (13)
C1	1.2349 (8)	0.7699 (2)	0.38553 (13)	0.0400 (10)
C2	1.3925 (9)	0.8068 (3)	0.43034 (14)	0.0482 (11)
C3	1.4602 (10)	0.7456 (3)	0.47251 (15)	0.0551 (12)
C4	1.3682 (9)	0.6477 (3)	0.46994 (13)	0.0489 (11)
C5	1.2137 (9)	0.6115 (2)	0.42448 (13)	0.0411 (10)
C6	1.1375 (8)	0.6695 (2)	0.38034 (12)	0.0344 (9)
C7	0.9826 (9)	0.6237 (2)	0.33364 (13)	0.0423 (11)
C8	0.8005 (9)	0.6605 (3)	0.29567 (13)	0.0464 (11)
C9	0.6625 (9)	0.6020 (3)	0.25107 (13)	0.0433 (11)
C10	0.5026 (8)	0.6542 (2)	0.20468 (12)	0.0386 (10)
C11	0.3737 (8)	0.5979 (2)	0.16350 (12)	0.0386 (10)
C12	0.2288 (8)	0.6434 (2)	0.12041 (12)	0.0377 (10)
C13	0.2083 (10)	0.7454 (3)	0.11687 (14)	0.0512 (12)
C14	0.3403 (11)	0.8019 (3)	0.15749 (15)	0.0572 (14)
C15	0.4858 (10)	0.7575 (3)	0.20135 (15)	0.0494 (11)
H2A	1.45350	0.87340	0.43210	0.0580*
H3A	1.56810	0.77070	0.50260	0.0660*
H4A	1.40930	0.60610	0.49850	0.0590*
H7A	1.02250	0.55590	0.33080	0.0510*
H8A	0.75310	0.72810	0.29640	0.0560*
H11A	0.38530	0.52900	0.16500	0.0460*
H13A	0.10710	0.77540	0.08750	0.0620*
H14A	0.33120	0.87080	0.15540	0.0680*
H15A	0.57290	0.79640	0.22870	0.0590*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0585 (3)	0.0625 (3)	0.0375 (2)	−0.0001 (2)	−0.0130 (2)	−0.0037 (2)
Cl1	0.0795 (7)	0.0395 (5)	0.0556 (6)	−0.0046 (4)	−0.0054 (5)	0.0095 (4)
Cl2	0.0904 (8)	0.0433 (5)	0.0526 (6)	−0.0130 (5)	−0.0208 (5)	0.0112 (4)
O1	0.140 (3)	0.0403 (16)	0.0538 (17)	0.0047 (16)	−0.0406 (19)	−0.0011 (13)
C1	0.0414 (18)	0.0401 (18)	0.0388 (18)	0.0025 (14)	0.0054 (15)	−0.0002 (14)
C2	0.048 (2)	0.0391 (19)	0.057 (2)	−0.0045 (15)	−0.0027 (18)	−0.0106 (17)
C3	0.055 (2)	0.063 (2)	0.046 (2)	−0.0017 (19)	−0.0109 (18)	−0.0121 (19)
C4	0.054 (2)	0.059 (2)	0.0326 (18)	0.0010 (17)	−0.0085 (16)	0.0005 (16)
C5	0.0442 (18)	0.0386 (18)	0.0397 (18)	−0.0044 (14)	−0.0064 (15)	0.0003 (15)
C6	0.0350 (16)	0.0346 (16)	0.0334 (16)	0.0022 (12)	−0.0016 (13)	−0.0028 (13)
C7	0.052 (2)	0.0357 (17)	0.0386 (18)	−0.0035 (14)	−0.0037 (16)	0.0023 (14)
C8	0.056 (2)	0.0400 (19)	0.0422 (19)	0.0092 (16)	−0.0095 (17)	−0.0037 (15)
C9	0.051 (2)	0.045 (2)	0.0334 (18)	0.0050 (15)	−0.0044 (15)	−0.0037 (15)
C10	0.0458 (19)	0.0355 (17)	0.0337 (17)	0.0019 (14)	−0.0057 (14)	−0.0033 (13)
C11	0.0445 (18)	0.0369 (17)	0.0346 (17)	0.0044 (14)	0.0028 (14)	0.0011 (14)
C12	0.0393 (17)	0.047 (2)	0.0262 (15)	0.0021 (14)	−0.0030 (13)	−0.0013 (14)
C13	0.062 (2)	0.052 (2)	0.039 (2)	0.0088 (17)	−0.0042 (17)	0.0087 (17)
C14	0.078 (3)	0.041 (2)	0.052 (2)	0.0057 (18)	−0.002 (2)	0.0036 (17)
C15	0.065 (2)	0.0416 (19)	0.0409 (19)	0.0018 (17)	−0.0048 (17)	−0.0043 (16)

Geometric parameters (Å, º) top

Br1—C12	1.900 (3)	C10—C15	1.396 (5)
Cl1—C1	1.735 (3)	C11—C12	1.368 (4)
Cl2—C5	1.737 (3)	C12—C13	1.379 (5)
O1—C9	1.205 (5)	C13—C14	1.375 (5)
C1—C2	1.376 (5)	C14—C15	1.378 (6)
C1—C6	1.412 (4)	C2—H2A	0.9300
C2—C3	1.377 (5)	C3—H3A	0.9300
C3—C4	1.370 (6)	C4—H4A	0.9300
C4—C5	1.382 (5)	C7—H7A	0.9300
C5—C6	1.397 (4)	C8—H8A	0.9300
C6—C7	1.458 (4)	C11—H11A	0.9300
C7—C8	1.286 (5)	C13—H13A	0.9300
C8—C9	1.474 (5)	C14—H14A	0.9300
C9—C10	1.498 (5)	C15—H15A	0.9300
C10—C11	1.380 (4)

Cl1—C1—C2	116.2 (2)	C11—C12—C13	121.4 (3)
Cl1—C1—C6	121.3 (2)	C12—C13—C14	118.8 (3)
C2—C1—C6	122.5 (3)	C13—C14—C15	120.7 (4)
C1—C2—C3	120.3 (4)	C10—C15—C14	120.0 (4)
C2—C3—C4	119.8 (4)	C1—C2—H2A	120.00
C3—C4—C5	119.2 (3)	C3—C2—H2A	120.00
Cl2—C5—C4	116.7 (3)	C2—C3—H3A	120.00
Cl2—C5—C6	119.4 (2)	C4—C3—H3A	120.00
C4—C5—C6	123.9 (3)	C3—C4—H4A	120.00
C1—C6—C5	114.3 (3)	C5—C4—H4A	120.00
C1—C6—C7	125.9 (3)	C6—C7—H7A	114.00
C5—C6—C7	119.8 (3)	C8—C7—H7A	114.00
C6—C7—C8	131.4 (3)	C7—C8—H8A	118.00
C7—C8—C9	123.9 (4)	C9—C8—H8A	118.00
O1—C9—C8	119.9 (3)	C10—C11—H11A	120.00
O1—C9—C10	120.4 (3)	C12—C11—H11A	120.00
C8—C9—C10	119.6 (3)	C12—C13—H13A	121.00
C9—C10—C11	118.6 (3)	C14—C13—H13A	121.00
C9—C10—C15	122.3 (3)	C13—C14—H14A	120.00
C11—C10—C15	119.1 (3)	C15—C14—H14A	120.00
C10—C11—C12	120.0 (3)	C10—C15—H15A	120.00
Br1—C12—C11	119.9 (2)	C14—C15—H15A	120.00
Br1—C12—C13	118.7 (2)

Cl1—C1—C2—C3	−178.4 (3)	C7—C8—C9—O1	10.9 (6)
C6—C1—C2—C3	−0.3 (5)	C7—C8—C9—C10	−169.8 (3)
Cl1—C1—C6—C5	178.3 (2)	O1—C9—C10—C11	−0.5 (5)
Cl1—C1—C6—C7	0.8 (5)	O1—C9—C10—C15	−179.2 (4)
C2—C1—C6—C5	0.2 (5)	C8—C9—C10—C11	−179.7 (3)
C2—C1—C6—C7	−177.3 (3)	C8—C9—C10—C15	1.6 (5)
C1—C2—C3—C4	−0.4 (6)	C9—C10—C11—C12	−179.4 (3)
C2—C3—C4—C5	1.2 (6)	C15—C10—C11—C12	−0.7 (5)
C3—C4—C5—Cl2	179.4 (3)	C9—C10—C15—C14	179.1 (4)
C3—C4—C5—C6	−1.3 (6)	C11—C10—C15—C14	0.4 (5)
Cl2—C5—C6—C1	179.9 (3)	C10—C11—C12—Br1	−179.9 (2)
Cl2—C5—C6—C7	−2.4 (4)	C10—C11—C12—C13	0.2 (5)
C4—C5—C6—C1	0.6 (5)	Br1—C12—C13—C14	−179.2 (3)
C4—C5—C6—C7	178.3 (3)	C11—C12—C13—C14	0.7 (5)
C1—C6—C7—C8	−26.8 (6)	C12—C13—C14—C15	−1.0 (6)
C5—C6—C7—C8	155.8 (4)	C13—C14—C15—C10	0.5 (6)
C6—C7—C8—C9	−179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···Cl1	0.93	2.54	3.128 (4)	122

Acknowledgements

CSCK extends his appreciation to the Vidya Vikas Research & Development Centre for the facilities and encouragement.

References

Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chandra Shekhara Shetty, T., Raghavendra, S., Chidan Kumar, C. S. & Dharmaprakash, S. M. (2016). Appl. Phys. B, 122, 205–213. Web of Science CrossRef Google Scholar
Chidan Kumar, C. S., Fun, H. K., Parlak, C., Rhyman, L., Ramasami, P., Tursun, M., Chandraju, S. & Quah, C. K. (2014). Spectrochim. Acta Part A, 132, 174–182. CrossRef CAS Google Scholar
Ekbote, A., Patil, P. S., Maidur, S. R., Chia, T. S. & Quah, C. K. (2017). Dyes Pigments, 139, 720–729. CrossRef CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CrossRef IUCr Journals Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814-3816. Web of Science CrossRef Google Scholar
Raghavendra, S., Chidan Kumar, C. S., Shetty, T. C. S., Lakshminarayana, B. N., Quah, C. K., Chandraju, S., Ananthnag, G. S., Gonsalves, R. A. & Dharmaprakash, S. M. (2017). Results Phys. 7, 2550–2556. Web of Science CrossRef Google Scholar
Rajendraprasad, S., Chidan Kumar, C. S., Quah, C. K., Chandraju, S., Lokanath, N. K., Naveen, S. & Warad, I. (2017). IUCrData, 2, x170379. Google Scholar
Rosli, M. M., Patil, P. S., Fun, H.-K., Razak, I. A. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o2501. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Teh, J. B.-J., Patil, P. S., Fun, H.-K., Satheesh, Y. E., Razak, I. A. & Dharmaprakash, S. M. (2007). Acta Cryst. E63, o1844–o1845. Web of Science CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). CrystalExplorer. University of Western Australia. Google Scholar

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