Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-di­chloro­phen­yl)-1-(2,5-di­chloro­thio­phen-3-yl)prop-2-en-1-one

Murthy, T.N.S.; Atioğlu, Z.; Akkurt, M.; Chidan Kumar, C.S.; Veeraiah, M.K.; Quah, C.K.; Siddaraju, B.P.

doi:10.1107/S2056989018010976

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Volume 74| Part 9| September 2018| Pages 1201-1205

https://doi.org/10.1107/S2056989018010976

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Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one

T. N. Sanjeeva Murthy,^a Zeliha Atioğlu,^b Mehmet Akkurt,^c ^* C. S. Chidan Kumar,^d M. K. Veeraiah,^e Ching Kheng Quah ^f and B. P. Siddaraju ^g

^aDepartment of Chemistry, Sri Siddhartha Academy of Higher Education, Tumkur 572 107, Karnataka, India, ^bİlke Education and Health Foundation, Cappadocia University, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, Turkey, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Engineering Chemistry, Vidya Vikas Institute of Engineering & Technology, Visvesvaraya Technological University, Alanahalli, Mysuru 570 028, Karnataka, India, ^eDepartment of Chemistry, Sri Siddhartha Institute of Technology, Tumkur 572 105, Karnataka, India, ^fX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^gDepartment of Chemistry, Cauvery Institute of Technology, Mandya 571 402, Karnataka, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 22 June 2018; accepted 1 August 2018; online 10 August 2018)

The molecular structure of the title compound, C₁₃H₆Cl₄OS, consists of a 2,5-dichlorothiophene ring and a 2,4-dichlorophenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-dichlorothiophene ring and the 2,4-dichlorophenyl ring is 12.24 (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. The molecular conformation is stabilized by intramolecular C—H⋯Cl contacts, producing S(6) and S(5) ring motifs. In the crystal, the molecules are linked along the a-axis direction through face-to-face π-stacking between the thiophene rings and the benzene rings of the molecules in zigzag sheets lying parallel to the bc plane along the c axis. The intermolecular interactions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are Cl⋯H/ H⋯Cl (20.8%), followed by Cl⋯Cl (18.7%), C⋯C (11.9%), Cl⋯S/S⋯Cl (10.9%), H⋯H (10.1%), C⋯H/H⋯C (9.3%) and O⋯H/H⋯O (7.6%).

Keywords: crystal structure; 2,5-dichlorothiophene ring; 2,4-dichlorophenyl ring; E configuration; Hirshfeld surface analysis.

CCDC reference: 1036797

1. Chemical context

Compounds bearing the 1,3-diphenyl-2-propen-1-one framework and belong to the flavonoid family are commonly called by its generic name `chalcone'. These are abundant in nature, ranging from ferns to higher plants, and are considered to be the precursors of flavonoids and isoflavonoids, in which the two aromatic rings are joined by a three carbon α,β-unsaturated carbonyl system. In plants, chalcones are converted to the corresponding (2S)-flavanones in a stereospecific reaction catalysed by the enzyme chalcone isomerase. The chemistry of chalcones remains a fascination among researchers because of the large number of replaceable hydrogen atoms that allows a number of derivatives with a variety of promising biological activities. They are found in fruits and vegetables, which attracted attention because of their pharmacological activities such as anti-inflamatory (Yadav et al., 2011 ), antifungal (Mahapatra et al., 2015 ), antiviral (Nowakowska, 2007 ; Chimenti et al., 2010 ; Elarfi &Al-Difar, 2012 ), antioxidant (Ferreira et al., 2006 ) and anticancer (Stiborova et al., 2011 activities). The synthesis and antimicrobial evaluation of new chalcones containing a 2,5-dichlorothiophene moiety has been reported (Tomar et al., 2007 ). In recent years, chalcones have been used in the field of materials science as non-linear optical devices (Raghavendra et al., 2017 ; Chandra Shekhara Shetty et al., 2016 ). In view of all the above and as part of our ongoing work (Harrison et al., 2010 ; Jasinski et al., 2010 ; Dutkiewicz et al., 2010 ) herewith we report the crystal and molecular structure of the title compound.

2. Structural commentary

The title compound, Fig. 1, is constructed from two aromatic rings (2,5-dichlorothiophene and terminal 2,4-dichlorophenyl rings), which are linked by a C=C—C(=O)—C enone bridge. Probably as a result of the steric repulsion between the chlorine atoms of the adjacent molecules, the C3—C4—C5—O1 and O1—C5—C6—C7 torsion angles about the enone bridge are −11.8 (5) and 0.4 (6)°, respectively. Hence, the dihedral angle between the 2,5-dichlorothiophene ring and the 2,4-dichlorophenyl ring increases to 12.24 (15)°. The bond lengths and angles in the title compound are comparable with those of the related compounds (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 ). 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.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯Cl1	0.93	2.48	3.220 (3)	136
C7—H7A⋯Cl3	0.93	2.65	3.075 (3)	108

Figure 1
The molecular structure of the title compound, showing the atom labelling and displacement ellipsoids drawn at the 50% probability level. The two intramolecular C—H⋯Cl contacts (see Table1) are shown as dashed lines.

3. Supramolecular features and Hirshfeld surface analysis

In the crystal, conventional hydrogen bonds are not observed. π-stacking is observed between the thiophene rings (S1/C1–C4, centroid Cg1) of adjacent molecules in the alternating sheets along the [100] direction [Cg1⋯Cg1^i,ii: centroid–centroid distance = 3.987 (2) Å, shortest perpendicular distance for the centroid of one ring to the plane of the other = 3.6143 (12) Å, ring-centroid offset = 1.683 Å; symmetry codes: (i) −1 + x, y, z; (i) 1 + x, y, z] and between the benzene rings (C8–C13, centroid Cg2) of the same molecules [Cg2⋯Cg2^i,ii: centroid–centroid distance = 3.987 (2) Å, shortest perpendicular distance = 3.5213 (13) Å, offset = 1.869 Å]. As shown Fig. 2, the molecules are packed to form zigzag sheets lying parallel to (011) along the c-axis direction through face-to-face π-stacking between the thiophene and benzene rings of pairs of adjacent molecules along the [100] direction (Cl⋯S and Cl⋯H interactions; Table 2 and Fig. 2). The Cl⋯S contact, at 3.660 (1) Å, is equal to the sum of the van der Waals radii of S and Cl atoms (3.65 Å; Pauling, 1960 ).

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

Contact	Distance	Symmetry operation
Cl2⋯S1	3.660 (1)	$[{1\over 2}]$ + x, $[{3\over 2}]$ − y, 2 − z
H10A⋯Cl4	3.03	− $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, 1 − z
C8⋯C9	3.573 (4)	1 + x, y, z

Figure 2
A view of the offset face-to-face π-stacking in the title compound, with the thick dashed lines indicating centroid-to-centroid interactions. The Cl⋯H and Cl⋯S interactions are also shown as dashed lines.

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 overall two-dimensional fingerprint plot for the title compound and those delineated into Cl⋯H/ H⋯Cl, Cl⋯Cl, C⋯C, Cl⋯S/S⋯Cl, H⋯H, C⋯H/H⋯C and O⋯H/H⋯O contacts are illustrated in Fig. 3; the percentage contributions from the different interatomic contacts to the Hirshfeld surfaces are as follows: Cl⋯H/ H⋯Cl (20.8%), Cl⋯Cl (18.7%), C⋯C (11.9%), Cl⋯S/S⋯Cl (10.9%), H⋯H (10.1%), C⋯H/H⋯C (9.3%) and O⋯H/H⋯O (7.6%). The contributions of the other weak intermolecular contacts to the Hirshfeld surfaces are Cl⋯C/C⋯Cl (3.6%), S⋯C/C⋯S (2.8%), Cl⋯O/O⋯Cl (2.3%), S⋯S (0.9%), O⋯O (0.6%) and C⋯O/O⋯C (0.6%).

Figure 3
The two-dimensional fingerprint plots of the title compound, showing (a) all interactions, and delineated into (b) Cl⋯H/ H⋯Cl, (c) Cl⋯Cl, (d) C⋯C, (e) Cl⋯S/S⋯Cl, (f) H⋯H, (g) C⋯H/H⋯C and (h) O⋯H/H⋯O interactions.

The C—H⋯Cl interactions appear as two distinct spikes in the fingerprint plot (Fig. 3b) of the title compound, where the sum of Cl⋯H/H⋯Cl interactions comprises 20.8% of the total Hirshfeld surface area of the molecule. The Cl⋯H/H⋯Cl interactions represented by the spikes in the bottom right and left region (d_e + d_i ≃ 2.83 Å) indicate that the hydrogen atoms are in contact with the Cl atoms to build the two-dimensional supramolecular framework [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively]. Cl⋯Cl contacts (Fig. 3c; 18.7%) are disfavoured when the number of H atoms on the molecular surface is large because of competition with the more attractive H⋯Cl contacts. Cl⋯Cl contacts from a parallel alignment of C—Cl bonds (C10—H10A⋯Cl4ⁱⁱⁱ; (iii) − $[{1\over 2}]$ + x, $[{3\over 2}]$ − y, 1 − z] may be indicated. They are known in the literature as type-I halogen–halogen interactions (Bui et al., 2009 ), with both C—Cl⋯Cl angles equal to one another. In the present case, these angles are close to 165°. The C⋯C contacts (Fig. 3d); 11.9%) reflect π–π interactions between the above-mentioned aromatic rings. The S⋯Cl contacts (Fig. 3e; 10.9%) contracted to a much lesser degree. The C⋯H/H⋯C interactions (Fig. 3g) account for 9.3% of the total Hirshfeld surface of the molecules. The scattered points in the breakdown of the fingerprint plot show the π–π stacking interactions. In the fingerprint plot delineated into H⋯O/O⋯H contacts (Fig. 3h), the 7.6% contribution to the Hirshfeld surface arises from intermolecular C=O⋯H hydrogen bonding and is viewed as pair of spikes with the tip at de + di ∼ 2.9 Å.

The large number of Cl⋯H/ H⋯Cl, Cl⋯Cl, C⋯C, Cl⋯S/S⋯Cl, H⋯H, C⋯H/H⋯C and O⋯H/H⋯O interactions suggest that van der Waals interactions and hydrogen bonding play the major roles in the crystal packing (Hathwar et al., 2015 ).

4. Database survey

The closest related compounds with the same skeleton and containing a similar bis-chalcone moiety to the title compound but with different substituents on the aromatic rings are: (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethylphenyl)prop-2-en-1-one [(I); Naik et al., 2015 ], (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethylphenyl)prop- 2-en-1-one [(II); Naik et al., 2015], (2E)-1-(5-chlorothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one [(III); Naik et al., 2015], (2E)-1-(5-bromothiophen-2-yl)-3-(4-ethoxyphenyl)prop-2-en-1-one [(IV); Naik et al., 2015], (2E)-3-(4-bromophenyl)-1-(5-chlorothiophen-2-yl)prop-2-en-1-one [(V); Naik et al., 2015], (2E)-1-(5-bromothiophen-2-yl)-3-(3-methoxyphenyl)prop-2-en-1-one [(VI); Naik et al., 2015], (E)-1-(5-chlorothiophen-2-yl)-3-(p-tolyl)prop-2-en-1-one [(VII); Kumara et al., 2017 ], (E)-1-(5-chlorothiophen-2-yl)-3-(2,4-dimethylphenyl) prop-2-en-1-one [(VIII); Naveen et al., 2016 ], (2E)-1-(5-bromothiophen- 2-yl)-3-(2-chlorophenyl)prop-2-en-1-one [(IX); Anitha et al., 2015 ], (2E)-1-[4-hydroxy-3-(morpholin-4-ylmethyl)phenyl]-3-(thiophen-2-yl)prop-2-en-1-one [(X); Yesilyurt et al., 2018 ] and (E)-1-(2-aminophenyl)-3-(thiophen-2-yl)prop-2-en-1-one [(XI); Chantrapromma et al., 2013 ].

In (I) and (II), the structures are isostructural in space group P1, while (III) and (IV) are isostructural in space group P2₁/c. There are no hydrogen bonds of any kind in the structures of compounds (I) and (II), but in the structures of compounds (III) and (IV), the molecules are linked into C(7) chains by means of C—H⋯O hydrogen bonds. In (V), there are again no hydrogen bonds nor π–π stacking interactions but in (VI), the molecules are linked into C(5) chains by C—H⋯O hydrogen bonds. In each of compounds (I)–(VI), the molecular skeletons are close to planarity, and there are short halogen–halogen contacts in the structures of compounds (II) and (V) and a short Br⋯O contact in the structure of compound (VI).

In (VII), the molecule is non-planar, with a dihedral angle of 22.6 (2)° between the aromatic rings. The molecules are linked by pairs of C—H⋯π interactions, forming inversion dimers. There are no other significant intermolecular interactions present. In (VIII), the molecule is nearly planar, the dihedral angle between the thiophene and phenyl rings being 9.07 (8)°. The molecules are linked via weak C—H⋯O and C—H⋯S hydrogen bonds, forming chains propagating along the c-axis direction. In (IX), the thienyl ring is not coplanar with the benzene ring, their planes forming a dihedral angle of 13.2 (4)°. In the crystal, molecules stack along the a-axis direction, with the interplanar separation between the thienyl rings and between the benzene rings being 3.925 (6) Å. In (X), the thiophene ring forms a dihedral angle of 26.04 (9)° with the benzene ring. The molecular conformation is stabilized by an O—H⋯N hydrogen bond. The molecules are connected through C—H⋯O hydrogen bonds, forming wave-like layers parallel to the ab plane, which are further linked into a three-dimensional network by C—H⋯π interactions. In (XI), the molecule is almost planar with a dihedral angle of 3.73 (8)° between the phenyl and thiophene rings. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. Adjacent molecules are linked into dimers in an anti-parallel face-to-face manner by pairs of C—H⋯O interactions. Neighboring dimers are further linked into chains along the c-axis direction by N—H⋯N hydrogen bonds.

5. Synthesis and crystallization

The title compound was synthesized as per the procedure reported earlier (Kumar et al., 2013a ,b ; Chidan Kumar et al., 2014 ). 1-(2,5-Dichlorothiophen-3-yl)ethanone (0.01 mol) (Harrison et al., 2010) and 2,4-dichlorobenzaldehyde (0.01 mol) was dissolved in 20 ml methanol. A catalytic amount of NaOH was added to the solution dropwise with vigorous stirring. The reaction mixture was stirred for about 2 h at room temperature. The formed crude products were filtered, washed successively with distilled water and recrystallized from methanol to get the title chalcone. The melting point (381–383 K) was determined by Stuart Scientific (UK) apparatus.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. C-bound H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å and U_iso(H) = 1.2U_eq(C) for C—H. Owing to poor agreement between observed and calculated intensities, twelve outliers (2 7 2, 2 8 0, 2 8 1, 0 1 28, 2 8 23, 0 14 8, 0 0 6, 3 0 29, 1 0 8, 0 17 4, 1 3 27, 2 12 19) were omitted in the final cycles of refinement.

Table 3
Experimental details

Crystal data
Chemical formula	C₁₃H₆Cl₄OS
M_r	352.04
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	294
a, b, c (Å)	3.9867 (3), 13.4564 (11), 25.573 (2)
V (Å³)	1371.91 (19)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.00
Crystal size (mm)	0.63 × 0.23 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007 )
T_min, T_max	0.757, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	11402, 4226, 3425
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.720

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.102, 1.03
No. of reflections	4226
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.20
Absolute structure	Flack x determined using 1124 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.04 (5)
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: 1036797

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989018010976/dx2006sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018010976/dx2006Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018010976/dx2006Isup3.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)-3-(2,4-Dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one top

Crystal data top

C₁₃H₆Cl₄OS	D_x = 1.704 Mg m⁻³
M_r = 352.04	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4362 reflections
a = 3.9867 (3) Å	θ = 2.2–28.5°
b = 13.4564 (11) Å	µ = 1.00 mm⁻¹
c = 25.573 (2) Å	T = 294 K
V = 1371.91 (19) Å³	Block, yellow
Z = 4	0.63 × 0.23 × 0.11 mm
F(000) = 704

Data collection top

Bruker APEXII CCD diffractometer	3425 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 30.8°, θ_min = 1.6°
T_min = 0.757, T_max = 0.894	h = −5→2
11402 measured reflections	k = −19→19
4226 independent reflections	l = −36→36

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0581P)² + 0.011P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.102	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.25 e Å⁻³
4226 reflections	Δρ_min = −0.20 e Å⁻³
172 parameters	Absolute structure: Flack x determined using 1124 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.04 (5)

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
C1	1.1673 (8)	0.77797 (19)	0.84012 (9)	0.0391 (6)
C2	1.2553 (8)	0.6794 (2)	0.91880 (10)	0.0419 (6)
C3	1.1115 (8)	0.6258 (2)	0.88062 (10)	0.0410 (6)
H3A	1.052432	0.559246	0.884223	0.049*
C4	1.0587 (8)	0.6820 (2)	0.83366 (10)	0.0382 (6)
C5	0.9016 (9)	0.6327 (2)	0.78763 (10)	0.0444 (7)
C6	0.7779 (10)	0.6938 (2)	0.74420 (11)	0.0493 (7)
H6A	0.809837	0.762158	0.746266	0.059*
C7	0.6253 (9)	0.6588 (2)	0.70264 (10)	0.0462 (7)
H7A	0.596005	0.590316	0.700760	0.055*
C8	0.4975 (8)	0.7177 (2)	0.65917 (10)	0.0386 (6)
C9	0.3384 (8)	0.67552 (19)	0.61621 (10)	0.0403 (6)
C10	0.2191 (8)	0.7316 (2)	0.57472 (10)	0.0431 (6)
H10A	0.112503	0.701315	0.546561	0.052*
C11	0.2620 (8)	0.8330 (2)	0.57612 (10)	0.0425 (7)
C12	0.4192 (9)	0.8788 (2)	0.61805 (11)	0.0465 (7)
H12A	0.447771	0.947373	0.618483	0.056*
C13	0.5316 (9)	0.8219 (2)	0.65879 (11)	0.0438 (7)
H13A	0.633719	0.852975	0.687101	0.053*
O1	0.8718 (9)	0.54311 (16)	0.78790 (9)	0.0721 (9)
S1	1.3313 (2)	0.80047 (5)	0.90119 (3)	0.04511 (19)
Cl1	1.1738 (3)	0.87633 (5)	0.79734 (3)	0.0556 (2)
Cl2	1.3606 (3)	0.63887 (6)	0.98017 (3)	0.0593 (2)
Cl3	0.2772 (3)	0.54840 (5)	0.61241 (3)	0.0639 (3)
Cl4	0.1204 (3)	0.90504 (6)	0.52453 (3)	0.0605 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0422 (17)	0.0375 (11)	0.0377 (11)	0.0021 (13)	0.0062 (12)	−0.0015 (9)
C2	0.0429 (18)	0.0443 (13)	0.0384 (12)	0.0015 (13)	−0.0020 (11)	0.0019 (10)
C3	0.0430 (18)	0.0392 (12)	0.0408 (12)	−0.0001 (13)	−0.0012 (12)	0.0003 (10)
C4	0.0376 (16)	0.0406 (12)	0.0364 (11)	0.0014 (12)	0.0021 (11)	−0.0021 (10)
C5	0.051 (2)	0.0462 (14)	0.0362 (12)	−0.0046 (14)	0.0005 (12)	−0.0046 (10)
C6	0.059 (2)	0.0451 (13)	0.0437 (13)	−0.0026 (15)	−0.0080 (14)	−0.0013 (11)
C7	0.058 (2)	0.0429 (13)	0.0382 (12)	−0.0006 (15)	0.0010 (14)	−0.0022 (10)
C8	0.0385 (16)	0.0415 (13)	0.0358 (11)	0.0001 (12)	0.0045 (11)	−0.0038 (10)
C9	0.0416 (16)	0.0380 (11)	0.0412 (12)	−0.0018 (13)	0.0027 (13)	−0.0046 (9)
C10	0.0433 (18)	0.0481 (13)	0.0378 (12)	0.0008 (13)	0.0001 (12)	−0.0066 (10)
C11	0.0387 (18)	0.0488 (14)	0.0401 (12)	0.0061 (13)	0.0018 (11)	0.0002 (10)
C12	0.048 (2)	0.0396 (13)	0.0522 (15)	−0.0007 (13)	0.0013 (14)	−0.0061 (11)
C13	0.0468 (19)	0.0422 (13)	0.0426 (13)	−0.0004 (13)	−0.0034 (13)	−0.0080 (11)
O1	0.123 (3)	0.0414 (11)	0.0517 (12)	−0.0110 (15)	−0.0209 (16)	−0.0012 (9)
S1	0.0504 (5)	0.0422 (3)	0.0427 (3)	−0.0035 (3)	−0.0008 (3)	−0.0055 (3)
Cl1	0.0766 (6)	0.0403 (3)	0.0498 (4)	−0.0043 (4)	−0.0001 (4)	0.0048 (3)
Cl2	0.0740 (6)	0.0589 (4)	0.0450 (3)	−0.0016 (4)	−0.0159 (4)	0.0056 (3)
Cl3	0.0883 (8)	0.0410 (3)	0.0625 (4)	−0.0127 (4)	−0.0148 (5)	−0.0023 (3)
Cl4	0.0684 (6)	0.0556 (4)	0.0576 (4)	0.0076 (4)	−0.0106 (4)	0.0080 (3)

Geometric parameters (Å, º) top

C1—C4	1.372 (4)	C7—C8	1.458 (4)
C1—Cl1	1.717 (3)	C7—H7A	0.9300
C1—S1	1.720 (3)	C8—C9	1.390 (4)
C2—C3	1.343 (4)	C8—C13	1.408 (4)
C2—Cl2	1.714 (3)	C9—C10	1.386 (4)
C2—S1	1.717 (3)	C9—Cl3	1.731 (3)
C3—C4	1.435 (4)	C10—C11	1.375 (4)
C3—H3A	0.9300	C10—H10A	0.9300
C4—C5	1.489 (4)	C11—C12	1.387 (4)
C5—O1	1.212 (4)	C11—Cl4	1.732 (3)
C5—C6	1.467 (4)	C12—C13	1.368 (4)
C6—C7	1.312 (4)	C12—H12A	0.9300
C6—H6A	0.9300	C13—H13A	0.9300

C4—C1—Cl1	130.8 (2)	C8—C7—H7A	117.1
C4—C1—S1	113.3 (2)	C9—C8—C13	116.5 (3)
Cl1—C1—S1	115.92 (16)	C9—C8—C7	122.7 (3)
C3—C2—Cl2	126.8 (2)	C13—C8—C7	120.9 (3)
C3—C2—S1	113.3 (2)	C10—C9—C8	122.6 (3)
Cl2—C2—S1	119.95 (17)	C10—C9—Cl3	116.5 (2)
C2—C3—C4	112.8 (3)	C8—C9—Cl3	120.8 (2)
C2—C3—H3A	123.6	C11—C10—C9	118.5 (3)
C4—C3—H3A	123.6	C11—C10—H10A	120.7
C1—C4—C3	110.5 (2)	C9—C10—H10A	120.7
C1—C4—C5	130.3 (2)	C10—C11—C12	121.2 (3)
C3—C4—C5	119.2 (3)	C10—C11—Cl4	119.7 (2)
O1—C5—C6	121.9 (3)	C12—C11—Cl4	119.2 (2)
O1—C5—C4	118.7 (3)	C13—C12—C11	119.2 (3)
C6—C5—C4	119.3 (3)	C13—C12—H12A	120.4
C7—C6—C5	124.6 (3)	C11—C12—H12A	120.4
C7—C6—H6A	117.7	C12—C13—C8	122.0 (3)
C5—C6—H6A	117.7	C12—C13—H13A	119.0
C6—C7—C8	125.7 (3)	C8—C13—H13A	119.0
C6—C7—H7A	117.1	C2—S1—C1	90.24 (13)

Cl2—C2—C3—C4	−179.6 (2)	C13—C8—C9—C10	0.3 (5)
S1—C2—C3—C4	0.7 (4)	C7—C8—C9—C10	−179.5 (3)
Cl1—C1—C4—C3	178.6 (3)	C13—C8—C9—Cl3	−179.3 (3)
S1—C1—C4—C3	0.2 (4)	C7—C8—C9—Cl3	0.9 (4)
Cl1—C1—C4—C5	−2.0 (6)	C8—C9—C10—C11	0.4 (5)
S1—C1—C4—C5	179.6 (3)	Cl3—C9—C10—C11	179.9 (3)
C2—C3—C4—C1	−0.6 (4)	C9—C10—C11—C12	−0.3 (5)
C2—C3—C4—C5	179.9 (3)	C9—C10—C11—Cl4	179.2 (2)
C1—C4—C5—O1	168.9 (4)	C10—C11—C12—C13	−0.3 (5)
C3—C4—C5—O1	−11.8 (5)	Cl4—C11—C12—C13	−179.9 (3)
C1—C4—C5—C6	−13.1 (5)	C11—C12—C13—C8	1.0 (5)
C3—C4—C5—C6	166.3 (3)	C9—C8—C13—C12	−1.0 (5)
O1—C5—C6—C7	0.4 (6)	C7—C8—C13—C12	178.8 (3)
C4—C5—C6—C7	−177.6 (3)	C3—C2—S1—C1	−0.5 (3)
C5—C6—C7—C8	179.5 (3)	Cl2—C2—S1—C1	179.8 (2)
C6—C7—C8—C9	179.9 (4)	C4—C1—S1—C2	0.1 (3)
C6—C7—C8—C13	0.1 (5)	Cl1—C1—S1—C2	−178.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···Cl1	0.93	2.48	3.220 (3)	136
C7—H7A···Cl3	0.93	2.65	3.075 (3)	108

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

Contact	Distance	Symmetry operation
Cl2···S1	3.660 (1)	1/2 + x, 3/2 - y, 2 - z
H10A···Cl4	3.03	-1/2 + x, 3/2 - y, 1 - z
C8···C9	3.573 (4)	1 + x, y, z

Acknowledgements

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

References

Anitha, B. R., Vinduvahini, M., Ravi, A. J. & Devarajegowda, H. C. (2015). Acta Cryst. E71, o930. Web of Science CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bui, T. T. T., Dahaoui, S., Lecomte, C., Desiraju, G. & Espinosa, E. (2009). Angew. Chem. Int. Ed. 48, 3838–3841. Web of Science CrossRef 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
Chantrapromma, S., Ruanwas, P., Boonnak, N. & Fun, H.-K. (2013). Acta Cryst. E69, o1004–o1005. CSD CrossRef CAS IUCr Journals 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 A, 132, 174–182. Web of Science CrossRef Google Scholar
Chimenti, F., Fioravanti, R., Bolasco, A., Chimenti, P., Secci, D., Rossi, F., Yanez, M., Orallo, F., Ortuso, F., Alcaro, S., Cirilli, R., Ferretti, R. & Sanna, M. L. (2010). Bioorg. Med. Chem. 18, 1273–1279. Web of Science CrossRef Google Scholar
Dutkiewicz, G., Chidan Kumar, C. S., Yathirajan, H. S., Narayana, B. & Kubicki, M. (2010). Acta Cryst. E66, o1139. Web of Science CrossRef IUCr Journals Google Scholar
Elarfi, M. J. & Al-Difar, H. A. (2012). Sci. Rev. Chem. Commun. 2, 103–107. Google Scholar
Escobar, C. A., Trujillo, A., Howard, J. A. K. & Fuentealba, M. (2012). Acta Cryst. E68, o887. CrossRef IUCr Journals Google Scholar
Ezhilarasi, K. S., Reuben Jonathan, D., Vasanthi, R., Revathi, B. K. & Usha, G. (2015). Acta Cryst. E71, o371–o372. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Ferreira, I. C. F. R., Queiroz, M. R. P., Vilas-Boas, M., Estevinho, L. M., Begouin, A. & Kirsch, G. (2006). Bioorg. Med. Chem. Lett. 16, 1384–1387. Web of Science CrossRef PubMed CAS Google Scholar
Harrison, W. T. A., Chidan Kumar, C. S., Yathirajan, H. S., Mayekar, A. N. & Narayana, B. (2010). Acta Cryst. E66, o2479. Web of Science CrossRef IUCr Journals Google Scholar
Hathwar, V. R., Sist, M., Jørgensen, M. R. V., Mamakhel, A. H., Wang, X., Hoffmann, C. M., Sugimoto, K., Overgaard, J. & Iversen, B. B. (2015). IUCrJ, 2, 563–574. Web of Science CSD CrossRef CAS PubMed IUCr Journals Google Scholar
Jasinski, J. P., Pek, A. E., Chidan Kumar, C. S., Yathirajan, H. S. & Mayekar, A. N. (2010). Acta Cryst. E66, o1717. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kumara, K., Naveen, S., Prabhudeva, M. G., Ajay Kumar, K., Lokanath, N. K. & Warad, I. (2017). IUCrData, 2, x170038. Google Scholar
Kumar, C. S. C., Loh, W. S., Ooi, C. W., Quah, C. K. & Fun, H. K. (2013a). Molecules, 18, 11996–12011. Web of Science CrossRef Google Scholar
Kumar, C. S. C., Loh, W. S., Ooi, C. W., Quah, C. K. & Fun, H. K. (2013b). Molecules, 18, 12707–12724. Web of Science CrossRef Google Scholar
Li, Z., Wang, Y., Peng, K., Chen, L. & Chu, S. (2012). Acta Cryst. E68, o776. CrossRef IUCr Journals Google Scholar
Mahapatra, D. K., Asati, V. & Bharti, S. K. (2015). Eur. J. Med. Chem. 92, 839–865. Web of Science CrossRef CAS Google Scholar
McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814–3816. Web of Science CrossRef Google Scholar
Naik, V. S., Yathirajan, H. S., Jasinski, J. P., Smolenski, V. A. & Glidewell, C. (2015). Acta Cryst. E71, 1093–1099. Web of Science CSD CrossRef IUCr Journals Google Scholar
Naveen, S., Prabhudeva, M. G., Ajay Kumar, K., Lokanath, N. K. & Abdoh, M. (2016). IUCrData, 1, x161974. Google Scholar
Nowakowska, Z. (2007). Eur. J. Med. Chem. 42, 125–137. Web of Science CrossRef PubMed CAS Google Scholar
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Pauling, L. (1960). The Nature of the Chemical Bond, 3rd ed. Ithaca, New York: Cornell University Press. 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stiborová, M., Poljaková, I., Martínková, E., Bořek-Dohalská, L., Eckschlager, T., Kizek, R. & Frei, E. (2011). Interdiscipl. Toxicol. 4, 98–105. Google Scholar
Tomar, V., Bhattacharjee, G., Kamaluddin & Kumar, A. (2007). Bioorg. Med. Chem. Lett. 17, 5321–5324. Google Scholar
Yadav, V. R., Prasad, S., Sung, B. & Aggarwal, B. B. (2011). Int. Immunopharmacol. 11, 295–309. Web of Science CrossRef CAS PubMed Google Scholar
Yesilyurt, F., Aydin, A., Gul, H. I., Akkurt, M. & Ozcelik, N. D. (2018). Acta Cryst. E74, 960–963. Web of Science CrossRef IUCr Journals Google Scholar

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