Crystal structure and Hirshfeld surface analysis of 2-(4-chloro­phen­yl)-4-(di­meth­oxy­meth­yl)-5-phenyl-1,3-thia­zole

Guseinov, F.I.; Kobrakov, K.I.; Shuvalova, E.V.; Tuzharov, E.I.; Akkurt, M.; Yıldırım, S. Ö.; Bhattarai, A.

doi:10.1107/S2056989022005564

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 78| Part 6| June 2022| Pages 675-678

https://doi.org/10.1107/S2056989022005564

Open

access

Crystal structure and Hirshfeld surface analysis of 2-(4-chlorophenyl)-4-(dimethoxymethyl)-5-phenyl-1,3-thiazole

Firudin I. Guseinov,^a,^b Konstantin I. Kobrakov,^a Elena V. Shuvalova,^a,^b Egor I. Tuzharov,^b Mehmet Akkurt,^c Sema Öztürk Yıldırım ^d,^e and Ajaya Bhattarai ^f ^*

^aKosygin State University of Russia, 117997 Moscow, Russian Federation, ^bN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991 Moscow, Russian Federation, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus 26470 Eskisehir, Turkey, ^eDepartment of Physics, Faculty of Science, Erciyes University, 38039 Kayseri, Turkey, and ^fDepartment of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal
^*Correspondence e-mail: ajaya.bhattarai@mmamc.tu.edu.np

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 17 May 2022; accepted 22 May 2022; online 27 May 2022)

In the title compound, C₁₈H₁₆ClNO₂S, the thiazole ring subtends dihedral angles of 13.12 (14) and 43.79 (14) ° with the attached chlorophenyl and phenyl rings, respectively. In the crystal, C—H⋯π interactions link the molecules, forming a three-dimensional network. The roles of the various intermolecular interactions were clarified by Hirshfeld surface analysis, which reveals that the most important contributions to the crystal packing are from H⋯H (39.2%), H⋯C/C⋯H (25.2%), Cl⋯H/H⋯Cl (11.4%) and O⋯H/H⋯O (8.0%) contacts.

Keywords: crystal structure; thiazole ring; chlorophenyl ring; C—H⋯π interactions; Hirshfeld surface analysis.

CCDC reference: 2174374

1. Chemical context

Thiazole and its derivatives have attracted much synthetic interest due to their antimicrobial, antiviral, anti-diabetic, diuretic, anticonvulsant, antioxidant, anti-HIV, analgesic, anti-inflammatory, neuroprotective and antitumor activities (Dondoni 2010 ; Grover & Jachak 2015 ). In fact, the thiazole moiety is a prominent structural feature in a variety of natural products, such as vitamin B and penicillin (Yariv et al., 2015 ). On the other hand, the thiazole synthon is also useful in coordination chemistry and catalytic transformations due to its coordination ability and non-covalent bond donor or acceptor character (Gurbanov et al., 2020 ). As part of our studies in this area, we now report the synthesis and structure of the title compound and quantify its intermolecular non-covalent interactions by Hirshfeld surface analysis.

2. Structural commentary

The molecular structure of the title compound is shown in Fig. 1. The central 1,3-thiazolidine ring (S1/N1C1–C3) makes dihedral angles of 13.12 (14) and 43.79 (14)°, respectively, with the chlorophenyl ring (C4–C9) and the phenyl ring (C13–C18). The dimethoxymethane moiety features one anti conformation [C2—C10—O2—C12 = 172.5 (2)°] and one gauche conformation [C2—C10—O1—C11 = −78.1 (3)°] for its pendant bonds. The molecular conformation may be consolidated by a weak intramolecular C5—H5⋯S1 contact [H5⋯S1 = 2.74 Å; C5—H5⋯S1 = 106°].

Figure 1
The title molecule with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features and Hirshfeld surface analysis

The extended structure features C—H⋯π interactions, forming a three-dimensional network (Table 1, Fig. 2) in which the thiazole ring accepts once such bond and the phenyl ring two, but no significant π–π stacking contacts are observed [shortest centroid–centroid separation = 4.1887 (16) Å]. A Hirshfeld surface analysis was performed, and two-dimensional fingerprint plots were created with Crystal Explorer17.5 (Turner et al., 2017 ) to quantify the intermolecular interactions present in the extended structure. Fig. 3 depicts the Hirshfeld surface projected on d_norm and the related colours reflecting various interactions. The C—H⋯Cl interaction is represented by the red spot on the surface. Fig. 4 depicts the two-dimensional fingerprint plots. The weak van der Waals H⋯H connections provide the most (39.2%, Fig. 4b) to the Hirshfeld surface. The other principal contributions to the overall surface are from C⋯H/H⋯C (25.2%, Fig. 4c), Cl⋯H/H⋯Cl (11.4%, Fig. 4d) and O⋯H/H⋯O (8.0%, Fig. 4e) interactions. The contributions of the remaining less important interactions are given in Table 2.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the C1–C3/S1/N1 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯S1	0.95	2.74	3.143 (3)	106
C6—H6⋯Cg3ⁱ	0.95	2.81	3.620 (3)	144
C12—H12C⋯Cg3ⁱⁱ	0.98	2.81	3.406 (3)	120
C15—H15⋯Cg1ⁱⁱⁱ	0.95	2.95	3.481 (3)	117
Symmetry codes: (i) ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) .

Table 2
Percentage contributions of interatomic contacts to the Hirshfeld surface for the title compound

Contact	Percentage contribution
H⋯H	39.2
H⋯C/C⋯H	25.2
Cl⋯H/H⋯Cl	11.4
O⋯H/H⋯O	8.0
S⋯H/H⋯S	5.1
N⋯H/H⋯N	3.9
C⋯C	2.4
Cl⋯C/C⋯Cl	1.7
S⋯C/C⋯S	1.5
Cl⋯Cl	0.6
S⋯S	0.2
O⋯C/C⋯O	0.1

Figure 2
The packing viewed along the a-axis direction with the C—H⋯π interactions indicated by dashed lines.

Figure 3
The three-dimensional Hirshfeld surface for the title compound, plotted over d_norm in the range −0.08 to +1.30 a.u.

Figure 4
A view of the two-dimensional fingerprint plots for the title compound, showing (a) all interactions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) Cl⋯H/H⋯Cl and (e) O⋯H/H⋯O interactions. The d_i and d_e values are the closest internal and external distances (in Å) from given points on the Hirshfeld surface.

4. Database survey

The most closely related four structures containing the 1,3-thiazole moiety are as follows: methyl(2-(cyclopentylidenehydrazono)-4-oxo-3-phenyl-1,3-thiazolidin-5-ylidene)acetate [Cambridge Structural Database (Groom et al., 2016 ) refcode GUVVAW (I); Akkurt et al., 2015 ], 2-(5-methyl-4-phenyl-1,3-thiazol-2-yl)-1-phenylethanol [EKEZUP (II); Rybakov et al., 2003 ], 2-{(E)-2-[(2-chlorophenyl)methylidene]hydrazin-1-yl}-4-phenyl-1,3-thiazole [WOJKOX (III); Mague et al., 2014 ] and 2-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-2,3-dihydro-1H-isoindole-1,3-dione [IQUHOT (IV); Saravanan et al., 2016 ].

In the crystal of (I), the thiazolidinyl ring (r.m.s. deviation = 0.024 Å) forms a dihedral angle of 65.13 (8)° with the attached phenyl ring. The molecular packing features C—H⋯O and C—H⋯π interactions, forming a three-dimensional network. In (II), molecules form extended chains through O—H⋯N hydrogen bonds and in (III), the two independent molecules are associated via complementary N—H⋯N hydrogen bonds into a dimer. These dimers are associated through weak C—H⋯Cl and C—H⋯S interactions into supramolecular chains propagating along the a-axis direction. In (IV), the molecules are linked via C—H⋯O interactions, which form C(7) chains propagating along [010]. In addition to this, weak π–π interactions are also observed.

5. Synthesis and crystallization

A mixture of 1-chloro-3,3-diethoxy-1-phenylpropan-2-one (0.769 g, 2 mmol) and 4-chlorobenzothioamide (0.514 g, 3 mmol) was refluxed in methanol (15 ml) for 3 h. Then, the solvent was distilled off in a rotary evaporator under a vacuum. The residue was recrystallized from diethyl ether. Crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of a acetone solution. Colourless solid, yield 0.891 g (86%); m.p. 401–402 K. Analysis calculated for C₁₈H₁₆ClNO₂S: C 62.51, H 4.66, N 4.05; found: C 62.47, H 4.61, N 4.01%. ¹H NMR (300 MHz, CDCl₃) δ 3.52 (6H, 2CH₃), 4.62 (1H, CH), 7.22–8.90 (9H, Ar). ¹³C NMR (75 MHz, CDCl₃) δ 169.6, 168.2, 154.4, 144.00, 142.4, 130.8, 129.6, 128.2, 127.4, 126.8, 126.00, 115.2 and 55.8. ESI–MS: m/z: 346.88 [M + H]⁺.

6. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 3. All H atoms bonded to C atoms were positioned geometrically (C—H = 0.93–1.00 Å) and constrained to ride on their parent atoms with U_iso(H) = 1.2–1.5U_eq(C)

Table 3
Experimental details

Crystal data
Chemical formula	C₁₈H₁₆ClNO₂S
M_r	345.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.6235 (1), 25.1848 (3), 9.8283 (1)
β (°)	96.504 (1)
V (Å³)	1628.92 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	3.34
Crystal size (mm)	0.2 × 0.12 × 0.04

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.638, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	31880, 3497, 3304
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.153, 1.12
No. of reflections	3497
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.52
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT2016/6 (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Supporting information

CCDC reference: 2174374

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989022005564/hb8023sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989022005564/hb8023Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989022005564/hb8023Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT2016/6 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020).

2-(4-Chlorophenyl)-4-(dimethoxymethyl)-5-phenyl-1,3-thiazole top

Crystal data top

C₁₈H₁₆ClNO₂S	F(000) = 720
M_r = 345.83	D_x = 1.410 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 6.6235 (1) Å	Cell parameters from 20657 reflections
b = 25.1848 (3) Å	θ = 3.5–79.0°
c = 9.8283 (1) Å	µ = 3.34 mm⁻¹
β = 96.504 (1)°	T = 100 K
V = 1628.92 (4) Å³	Block, colourless
Z = 4	0.2 × 0.12 × 0.04 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix diffractometer	3497 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	3304 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.064
Detector resolution: 10.0000 pixels mm^-1	θ_max = 79.5°, θ_min = 3.5°
ω scans	h = −7→8
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −32→32
T_min = 0.638, T_max = 1.000	l = −12→12
31880 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0621P)² + 4.0625P] where P = (F_o² + 2F_c²)/3
3497 reflections	(Δ/σ)_max = 0.001
210 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.52 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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
Cl1	1.46338 (11)	0.46239 (3)	0.83382 (7)	0.0279 (2)
S1	0.51773 (10)	0.42961 (2)	0.43335 (7)	0.01922 (18)
O1	0.4944 (3)	0.23523 (8)	0.4398 (2)	0.0232 (4)
O2	0.2192 (3)	0.27028 (8)	0.5252 (2)	0.0234 (4)
N1	0.6210 (4)	0.33759 (9)	0.5297 (2)	0.0195 (5)
C1	0.6779 (4)	0.38728 (11)	0.5353 (3)	0.0197 (5)
C2	0.4449 (4)	0.33113 (11)	0.4441 (3)	0.0194 (5)
C3	0.3640 (4)	0.37626 (10)	0.3799 (3)	0.0184 (5)
C4	0.8675 (4)	0.40656 (11)	0.6128 (3)	0.0195 (5)
C5	0.9086 (4)	0.46059 (11)	0.6290 (3)	0.0204 (5)
H5	0.809694	0.485762	0.593256	0.025*
C6	1.0909 (4)	0.47816 (11)	0.6960 (3)	0.0210 (5)
H6	1.118224	0.515046	0.706735	0.025*
C7	1.2333 (4)	0.44064 (12)	0.7474 (3)	0.0213 (6)
C8	1.1971 (4)	0.38669 (12)	0.7341 (3)	0.0229 (6)
H8	1.296580	0.361728	0.770269	0.028*
C9	1.0129 (4)	0.36970 (11)	0.6669 (3)	0.0217 (6)
H9	0.985437	0.332781	0.657512	0.026*
C10	0.3501 (4)	0.27646 (11)	0.4245 (3)	0.0194 (5)
H10	0.270809	0.274179	0.331869	0.023*
C11	0.5988 (5)	0.22879 (13)	0.3220 (3)	0.0296 (7)
H11A	0.501099	0.230402	0.239378	0.044*
H11B	0.667819	0.194318	0.326277	0.044*
H11C	0.699242	0.257220	0.319221	0.044*
C12	0.0998 (5)	0.22282 (13)	0.5072 (3)	0.0315 (7)
H12A	0.051128	0.218272	0.410015	0.047*
H12B	−0.016708	0.225524	0.560094	0.047*
H12C	0.183243	0.192197	0.539363	0.047*
C13	0.1824 (4)	0.38355 (11)	0.2793 (3)	0.0188 (5)
C14	−0.0001 (4)	0.35859 (11)	0.2967 (3)	0.0201 (5)
H14	−0.009865	0.337216	0.375383	0.024*
C15	−0.1681 (5)	0.36470 (12)	0.2001 (3)	0.0239 (6)
H15	−0.291864	0.347268	0.212459	0.029*
C16	−0.1560 (5)	0.39635 (12)	0.0848 (3)	0.0248 (6)
H16	−0.270937	0.400469	0.018481	0.030*
C17	0.0259 (5)	0.42183 (12)	0.0677 (3)	0.0245 (6)
H17	0.034629	0.443579	−0.010394	0.029*
C18	0.1943 (4)	0.41573 (11)	0.1636 (3)	0.0213 (6)
H18	0.317831	0.433298	0.151148	0.026*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0244 (4)	0.0301 (4)	0.0270 (4)	−0.0046 (3)	−0.0063 (3)	0.0036 (3)
S1	0.0205 (3)	0.0162 (3)	0.0206 (3)	0.0005 (2)	0.0007 (2)	0.0009 (2)
O1	0.0250 (10)	0.0203 (10)	0.0236 (10)	0.0031 (8)	−0.0004 (8)	−0.0006 (7)
O2	0.0281 (11)	0.0210 (10)	0.0217 (10)	−0.0055 (8)	0.0051 (8)	0.0013 (8)
N1	0.0219 (12)	0.0199 (11)	0.0168 (10)	0.0006 (9)	0.0024 (9)	0.0009 (8)
C1	0.0238 (14)	0.0192 (13)	0.0169 (12)	0.0028 (10)	0.0056 (10)	0.0010 (10)
C2	0.0216 (14)	0.0203 (13)	0.0167 (12)	0.0004 (10)	0.0044 (10)	−0.0005 (10)
C3	0.0195 (13)	0.0181 (12)	0.0180 (12)	−0.0005 (10)	0.0030 (10)	−0.0006 (9)
C4	0.0210 (13)	0.0216 (13)	0.0165 (12)	0.0016 (10)	0.0044 (10)	−0.0005 (10)
C5	0.0183 (13)	0.0228 (13)	0.0204 (13)	0.0037 (10)	0.0029 (10)	0.0014 (10)
C6	0.0230 (14)	0.0200 (13)	0.0205 (13)	−0.0015 (10)	0.0047 (11)	−0.0005 (10)
C7	0.0204 (13)	0.0278 (14)	0.0161 (12)	−0.0009 (11)	0.0031 (10)	0.0002 (10)
C8	0.0239 (14)	0.0242 (14)	0.0204 (13)	0.0045 (11)	0.0009 (11)	0.0013 (10)
C9	0.0254 (14)	0.0191 (13)	0.0209 (13)	0.0009 (10)	0.0032 (11)	0.0002 (10)
C10	0.0193 (13)	0.0204 (13)	0.0180 (12)	0.0001 (10)	0.0000 (10)	0.0012 (10)
C11	0.0258 (15)	0.0309 (16)	0.0323 (16)	0.0035 (12)	0.0051 (12)	−0.0037 (12)
C12	0.0367 (18)	0.0257 (15)	0.0318 (16)	−0.0109 (13)	0.0028 (13)	0.0037 (12)
C13	0.0220 (14)	0.0183 (12)	0.0160 (12)	0.0025 (10)	0.0014 (10)	−0.0011 (9)
C14	0.0205 (13)	0.0211 (13)	0.0191 (12)	0.0024 (10)	0.0044 (10)	0.0007 (10)
C15	0.0231 (14)	0.0247 (14)	0.0241 (14)	0.0024 (11)	0.0035 (11)	−0.0017 (11)
C16	0.0243 (14)	0.0275 (14)	0.0212 (13)	0.0075 (11)	−0.0031 (11)	−0.0015 (11)
C17	0.0319 (16)	0.0240 (14)	0.0176 (13)	0.0051 (12)	0.0024 (11)	0.0022 (10)
C18	0.0238 (14)	0.0186 (12)	0.0224 (13)	0.0004 (10)	0.0057 (11)	0.0008 (10)

Geometric parameters (Å, º) top

Cl1—C7	1.747 (3)	C8—C9	1.387 (4)
S1—C1	1.740 (3)	C9—H9	0.9500
S1—C3	1.731 (3)	C10—H10	1.0000
O1—C10	1.408 (3)	C11—H11A	0.9800
O1—C11	1.424 (4)	C11—H11B	0.9800
O2—C10	1.396 (3)	C11—H11C	0.9800
O2—C12	1.433 (4)	C12—H12A	0.9800
N1—C1	1.306 (4)	C12—H12B	0.9800
N1—C2	1.368 (4)	C12—H12C	0.9800
C1—C4	1.475 (4)	C13—C14	1.391 (4)
C2—C3	1.379 (4)	C13—C18	1.406 (4)
C2—C10	1.517 (4)	C14—H14	0.9500
C3—C13	1.480 (4)	C14—C15	1.387 (4)
C4—C5	1.393 (4)	C15—H15	0.9500
C4—C9	1.399 (4)	C15—C16	1.395 (4)
C5—H5	0.9500	C16—H16	0.9500
C5—C6	1.381 (4)	C16—C17	1.392 (4)
C6—H6	0.9500	C17—H17	0.9500
C6—C7	1.389 (4)	C17—C18	1.384 (4)
C7—C8	1.383 (4)	C18—H18	0.9500
C8—H8	0.9500

C3—S1—C1	89.91 (13)	O2—C10—C2	107.0 (2)
C10—O1—C11	112.6 (2)	O2—C10—H10	109.6
C10—O2—C12	112.6 (2)	C2—C10—H10	109.6
C1—N1—C2	111.2 (2)	O1—C11—H11A	109.5
N1—C1—S1	114.1 (2)	O1—C11—H11B	109.5
N1—C1—C4	124.2 (3)	O1—C11—H11C	109.5
C4—C1—S1	121.6 (2)	H11A—C11—H11B	109.5
N1—C2—C3	116.3 (2)	H11A—C11—H11C	109.5
N1—C2—C10	119.9 (2)	H11B—C11—H11C	109.5
C3—C2—C10	123.8 (3)	O2—C12—H12A	109.5
C2—C3—S1	108.4 (2)	O2—C12—H12B	109.5
C2—C3—C13	130.7 (3)	O2—C12—H12C	109.5
C13—C3—S1	120.8 (2)	H12A—C12—H12B	109.5
C5—C4—C1	121.6 (3)	H12A—C12—H12C	109.5
C5—C4—C9	119.2 (3)	H12B—C12—H12C	109.5
C9—C4—C1	119.2 (2)	C14—C13—C3	120.9 (2)
C4—C5—H5	119.4	C14—C13—C18	119.3 (3)
C6—C5—C4	121.1 (3)	C18—C13—C3	119.8 (3)
C6—C5—H5	119.4	C13—C14—H14	119.8
C5—C6—H6	120.8	C15—C14—C13	120.4 (3)
C5—C6—C7	118.4 (3)	C15—C14—H14	119.8
C7—C6—H6	120.8	C14—C15—H15	119.9
C6—C7—Cl1	118.8 (2)	C14—C15—C16	120.3 (3)
C8—C7—Cl1	119.1 (2)	C16—C15—H15	119.9
C8—C7—C6	122.1 (3)	C15—C16—H16	120.3
C7—C8—H8	120.6	C17—C16—C15	119.4 (3)
C7—C8—C9	118.8 (3)	C17—C16—H16	120.3
C9—C8—H8	120.6	C16—C17—H17	119.7
C4—C9—H9	119.8	C18—C17—C16	120.6 (3)
C8—C9—C4	120.5 (3)	C18—C17—H17	119.7
C8—C9—H9	119.8	C13—C18—H18	120.0
O1—C10—C2	112.9 (2)	C17—C18—C13	120.0 (3)
O1—C10—H10	109.6	C17—C18—H18	120.0
O2—C10—O1	108.1 (2)

Cl1—C7—C8—C9	179.2 (2)	C3—C2—C10—O1	150.2 (3)
S1—C1—C4—C5	12.2 (4)	C3—C2—C10—O2	−90.9 (3)
S1—C1—C4—C9	−165.3 (2)	C3—C13—C14—C15	−178.5 (3)
S1—C3—C13—C14	−137.1 (2)	C3—C13—C18—C17	178.7 (2)
S1—C3—C13—C18	43.4 (3)	C4—C5—C6—C7	0.0 (4)
N1—C1—C4—C5	−172.0 (3)	C5—C4—C9—C8	−0.9 (4)
N1—C1—C4—C9	10.5 (4)	C5—C6—C7—Cl1	−179.4 (2)
N1—C2—C3—S1	−0.9 (3)	C5—C6—C7—C8	−0.4 (4)
N1—C2—C3—C13	177.8 (3)	C6—C7—C8—C9	0.2 (4)
N1—C2—C10—O1	−29.8 (3)	C7—C8—C9—C4	0.5 (4)
N1—C2—C10—O2	89.1 (3)	C9—C4—C5—C6	0.7 (4)
C1—S1—C3—C2	0.5 (2)	C10—C2—C3—S1	179.0 (2)
C1—S1—C3—C13	−178.4 (2)	C10—C2—C3—C13	−2.2 (5)
C1—N1—C2—C3	1.0 (3)	C11—O1—C10—O2	163.7 (2)
C1—N1—C2—C10	−179.0 (2)	C11—O1—C10—C2	−78.1 (3)
C1—C4—C5—C6	−176.8 (2)	C12—O2—C10—O1	−65.6 (3)
C1—C4—C9—C8	176.6 (2)	C12—O2—C10—C2	172.5 (2)
C2—N1—C1—S1	−0.5 (3)	C13—C14—C15—C16	−0.5 (4)
C2—N1—C1—C4	−176.6 (2)	C14—C13—C18—C17	−0.7 (4)
C2—C3—C13—C14	44.2 (4)	C14—C15—C16—C17	−0.1 (4)
C2—C3—C13—C18	−135.2 (3)	C15—C16—C17—C18	0.4 (4)
C3—S1—C1—N1	0.0 (2)	C16—C17—C18—C13	0.1 (4)
C3—S1—C1—C4	176.2 (2)	C18—C13—C14—C15	1.0 (4)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the C1–C3/S1/N1 and C13–C18 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···S1	0.95	2.74	3.143 (3)	106
C6—H6···Cg3ⁱ	0.95	2.81	3.620 (3)	144
C12—H12C···Cg3ⁱⁱ	0.98	2.81	3.406 (3)	120
C15—H15···Cg1ⁱⁱⁱ	0.95	2.95	3.481 (3)	117

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

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

Contact	Percentage contribution
H···H	39.2
H···C/C···H	25.2
Cl···H/H···Cl	11.4
O···H/H···O	8.0
S···H/H···S	5.1
N···H/H···N	3.9
C···C	2.4
Cl···C/C···Cl	1.7
S···C/C···S	1.5
Cl···Cl	0.6
S···S	0.2
O···C/C···O	0.1

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

Contact	Distance	Symmetry operation
Cl1···H16	2.85	2 + x, y, 1 + z
H18···Cl1	3.00	2 - x, 1 - y, 1 - z
H11C···H15	2.50	1 + x, y, z
H6···C17	2.97	1 - x, 1 - y, 1 - z
O2···H11A	2.65	x, 1/2 - y, 1/2 + z
C7···H17	2.85	1 + x, y, 1 + z
C11···H8	3.04	-1 + x, 1/2 - y, -1/2 + z

Acknowledgements

The authors' contributions are as follows. Conceptualization, FIG, MA and AB; synthesis, FIG and KIK; X-ray analysis, EVS, EIT, MA and SÖY; writing (review and editing of the manuscript), FIG, MA, SÖY and AB.

References

Akkurt, M., Smolenski, V. A., Mohamed, S. K., Jasinski, J. P., Hassan, A. A. & Albayati, M. R. (2015). Acta Cryst. E71, o776–o777. CSD CrossRef IUCr Journals Google Scholar
Dondoni, A. (2010). Org. Biomol. Chem. 8, 3366–3385. CrossRef CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals 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
Grover, J. & Jachak, S. M. (2015). RSC Adv. 5, 38892–38905. CrossRef CAS Google Scholar
Gurbanov, A. V., Kuznetsov, M. L., Demukhamedova, S. D., Alieva, I. N., Godjaev, N. M., Zubkov, F. I., Mahmudov, K. T. & Pombeiro, A. J. L. (2020). CrystEngComm, 22, 628–633. Web of Science CSD CrossRef CAS Google Scholar
Mague, J. T., Mohamed, S. K., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2014). Acta Cryst. E70, o907–o908. CSD CrossRef IUCr Journals Google Scholar
Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Rybakov, V. B., Liakina, A. Y., Popova, I. S., Formanovsky, A. A. & Aslanov, L. A. (2003). Acta Cryst. E59, o1293–o1295. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saravanan, K., Archana, K., Lakshmithendral, K., Kabilan, S. & Selvanayagam, S. (2016). IUCrData, 1, x161053. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. https://hirshfeldsurface.net Google Scholar
Yariv, I., Lipovsky, A., Gedanken, A., Lubart, R. & Fixler, D. (2015). Int. J. Nanomedicine, 10, 3593–3601. CAS PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.