2-(4-Chloro-3-nitro­phen­yl)-4-(4-chloro­phen­yl)-1,3-thia­zole

Nayak, S.K.; Venugopala, K.N.; Chopra, D.; Govender, T.; Kruger, H.G.; Maguire, G.E.M.; Guru Row, T.N.

doi:10.1107/S1600536809039543

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Pages o2611-o2612

https://doi.org/10.1107/S1600536809039543

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2-(4-Chloro-3-nitrophenyl)-4-(4-chlorophenyl)-1,3-thiazole

Susanta K. Nayak,^a K. N. Venugopala,^b Deepak Chopra,^c ^* Thavendran Govender,^d Hendrik G. Kruger,^b Glenn E. M. Maguire ^b and T. N. Guru Row ^a

^aSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, India, ^bSchool of Chemistry, University of KwaZulu-Natal, Durban 4000, South Africa, ^cDepartment of Chemistry, Indian Institute of Science Education and Research, Bhopal 462 023, India, and ^dSchool of Pharmacy and Pharmacology, University of Kwazulu-Natal, Durban 4000, South Africa
^*Correspondence e-mail: dchopra@iiserbhopal.ac.in

(Received 14 September 2009; accepted 29 September 2009; online 3 October 2009)

The title compound, C₁₅H₈Cl₂N₂O₂S, crystallizes with two molecules in the asymmetric unit. The dihedral angles between the 4-chloro-3-nitrophenyl ring and the thiazole ring are 0.5 (1) and 7.1 (1)° and those between the 4-chlorophenyl ring and the thiazole ring are 7.1 (1) and 7.4 (1)° in the two molecules. The crystal structure is stabilized by intermolecular C—H⋯Cl and C—H⋯O hydrogen bonds.

Related literature

The aminothiazole ring system is a useful structural element in medicinal chemistry and has found broad applications in drug development, see: Fortuna et al. (1988 ); Frank et al. (1995 ); Karl et al. (1983 ); Tsuji & Ishikawa (1994 ).

Experimental

Crystal data

C₁₅H₈Cl₂N₂O₂S
M_r = 351.20
Triclinic, $[P \overline 1]$
a = 7.4379 (19) Å
b = 12.305 (3) Å
c = 16.808 (4) Å
α = 88.596 (5)°
β = 84.131 (4)°
γ = 76.721 (5)°
V = 1489.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.58 mm⁻¹
T = 292 K
0.28 × 0.24 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.854, T_max = 0.918
14507 measured reflections
5235 independent reflections
2855 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.130
S = 0.97
5235 reflections
397 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1ⁱ	0.93	2.48	3.285 (5)	145
C15′—H15′⋯Cl2ⁱⁱ	0.93	2.73	3.610 (4)	158
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and CAMERON (Watkin et al., 1993 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809039543/fj2246sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809039543/fj2246Isup2.hkl

checkCIF report

Comment top

The aminothiazole ring system is a useful structural element in medicinal chemistry and has found broad applications in drug development as antiallergies (Karl et al., 1983), anti-inflammatory (Fortuna et al., 1988), antibacterial (Tsuji et al., 1994) and anti-HIV agents (Frank et al., 1995]. In view of different applications of this class of compounds, we have undertaken a single-crystal structure determination of the title compound. The compound is completely planar with the nitro group not planar with the 4-chloro-4-nitrophenyl ring to avoid electrostatic repulsion with the chlorine atom in an ortho position, the dihedral twist being 35.4 (3)° and 48.1 (3)° respectively in the two molecules. Relevant torsion angles are given in Table 1. Figure 1 gives an ORTEP view depicting two molecules (A) and (B) in the asymmetric unit. The C—N bond lengths of the five-membered thiazoyl ring is different indicating that the electrnoic environment around each nitrogen atom is different. The torsion angles N2—C7—C1—C6/N2'-C7'-C1'-C6' and N2—C9—C10—C11/N2'-C9'-C10'-C11'are nearly equal to 180° indicating delocalization of the π electron density between all the three aromatic moieties, namely the thiazoyl ring and the adjacent aryl rings. The crystal structure is stabilized by C—H···O intermolecular hydrogen bonds (between molecules of the 'A' type), each of which are held by C—H···Cl intermolecular interactions (with molecules of 'B' type) between them (Figure 2).

Related literature top

The aminothiazole ring system is a useful structural element in medicinal chemistry and has found broad applications in drug development, see: Fortuna et al. (1988); Frank et al. (1995); Karl et al. (1983); Tsuji & Ishikawa (1994).

Experimental top

A mixture of 4-chloro-3-nitrobenzonitrile, (0.1 mol), thioacetic acid (0.1 mol), boron trifluoride diethyletherate (0.1 mol) and 1,2 dichloro ethane was refluxed for 1 h at 80 C. The reaction medium was quenched with 1 N hydrochloric acid (congo red) and the obtained product i.e 4-chloro-3-nitrobenzothioamide was isolated with dichloromethane. The solvent was evaporated at reduced pressure and the crude product (Yield = 89%) left behind was recrystallized from ethyl acetate. This was taken with 2-bromo-1-(4-chlorophenyl)ethanone (0.1 mol) in absolute ethanol medium was refluxed under nitrogen atmosphere for 2 h at 80 C. Reaction medium was cooled to room temperature and poured into 50 ml of water containing sodium acetate. The precipitate obtained was filtered and recrystallized from ethanol. (Yield: 92%) and the melting point was 128–129 C.

Structure description top

The aminothiazole ring system is a useful structural element in medicinal chemistry and has found broad applications in drug development, see: Fortuna et al. (1988); Frank et al. (1995); Karl et al. (1983); Tsuji & Ishikawa (1994).

Computing details top

Data collection: SMART (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. : Molecular structure shows the atom labelling Scheme with displacement ellipsoids for non-H atoms at 50% probability level, hydrogen atoms are arbitary circle.
	Fig. 2. : The molecular packing depicting C—H···O and C—H···Cl intermolecular interactions in the solid state.

2-(4-Chloro-3-nitrophenyl)-4-(4-chlorophenyl)-1,3-thiazole top

Crystal data top

C₁₅H₈Cl₂N₂O₂S	Z = 4
M_r = 351.20	F(000) = 712
Triclinic, P1	D_x = 1.566 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4379 (19) Å	Cell parameters from 320 reflections
b = 12.305 (3) Å	θ = 1.0–28.0°
c = 16.808 (4) Å	µ = 0.58 mm⁻¹
α = 88.596 (5)°	T = 292 K
β = 84.131 (4)°	Plate, colorless
γ = 76.721 (5)°	0.28 × 0.24 × 0.15 mm
V = 1489.3 (6) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	5235 independent reflections
Radiation source: fine-focus sealed tube	2855 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.854, T_max = 0.918	k = −14→14
14507 measured reflections	l = −19→19

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0568P)²] where P = (F_o² + 2F_c²)/3
5235 reflections	(Δ/σ)_max = 0.001
397 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₈Cl₂N₂O₂S	γ = 76.721 (5)°
M_r = 351.20	V = 1489.3 (6) Å³
Triclinic, P1	Z = 4
a = 7.4379 (19) Å	Mo Kα radiation
b = 12.305 (3) Å	µ = 0.58 mm⁻¹
c = 16.808 (4) Å	T = 292 K
α = 88.596 (5)°	0.28 × 0.24 × 0.15 mm
β = 84.131 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5235 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2855 reflections with I > 2σ(I)
T_min = 0.854, T_max = 0.918	R_int = 0.042
14507 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 0.97	Δρ_max = 0.34 e Å⁻³
5235 reflections	Δρ_min = −0.21 e Å⁻³
397 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
S1	0.28130 (14)	−0.08178 (8)	1.08929 (6)	0.0671 (3)
S1'	0.55762 (17)	0.57562 (10)	0.65181 (7)	0.0872 (4)
Cl2'	1.01634 (16)	0.76240 (10)	0.20368 (8)	0.1005 (4)
Cl2	0.02483 (18)	−0.26482 (9)	0.64160 (7)	0.0962 (4)
Cl1'	0.55818 (19)	0.00327 (11)	0.69174 (8)	0.1110 (5)
Cl1	0.3241 (2)	0.48445 (10)	1.11376 (8)	0.1125 (5)
N2	0.2343 (4)	0.0036 (2)	0.95110 (18)	0.0511 (7)
N2'	0.7301 (4)	0.4815 (2)	0.52398 (18)	0.0561 (8)
C1	0.2750 (4)	0.1409 (3)	1.0459 (2)	0.0477 (8)
C9	0.2261 (4)	−0.1062 (3)	0.9456 (2)	0.0501 (9)
C10'	0.8033 (5)	0.6361 (3)	0.4402 (2)	0.0572 (10)
C1'	0.6345 (5)	0.3473 (3)	0.6178 (2)	0.0558 (10)
C2	0.2580 (4)	0.2243 (3)	0.9895 (2)	0.0514 (9)
H2	0.2385	0.2088	0.9376	0.062*
C10	0.1895 (4)	−0.1486 (3)	0.8695 (2)	0.0506 (9)
C7	0.2621 (4)	0.0289 (3)	1.0228 (2)	0.0497 (9)
C9'	0.7236 (5)	0.5945 (3)	0.5149 (2)	0.0582 (10)
C3	0.2695 (5)	0.3300 (3)	1.0087 (2)	0.0551 (9)
N1	0.2537 (5)	0.4131 (3)	0.9443 (3)	0.0807 (11)
C3'	0.6725 (5)	0.1531 (4)	0.5877 (2)	0.0627 (10)
C2'	0.6890 (5)	0.2590 (3)	0.5648 (2)	0.0575 (10)
H2'	0.7373	0.2712	0.5129	0.069*
C4	0.3003 (5)	0.3551 (3)	1.0859 (3)	0.0650 (10)
C12	0.1416 (5)	−0.2967 (3)	0.7884 (3)	0.0694 (11)
H12	0.1406	−0.3715	0.7822	0.083*
C15'	0.8695 (5)	0.5650 (3)	0.3768 (2)	0.0627 (10)
H15'	0.8679	0.4899	0.3830	0.075*
C13	0.0966 (5)	−0.2213 (3)	0.7275 (2)	0.0657 (11)
C6'	0.5613 (5)	0.3250 (4)	0.6947 (2)	0.0728 (12)
H6'	0.5253	0.3824	0.7320	0.087*
C5'	0.5417 (5)	0.2198 (4)	0.7162 (2)	0.0770 (13)
H5'	0.4892	0.2076	0.7673	0.092*
C15	0.1492 (5)	−0.0769 (3)	0.8060 (2)	0.0617 (10)
H15	0.1539	−0.0025	0.8110	0.074*
C14	0.1024 (5)	−0.1121 (3)	0.7358 (2)	0.0692 (11)
H14	0.0748	−0.0619	0.6940	0.083*
C11	0.1880 (5)	−0.2598 (3)	0.8587 (3)	0.0663 (11)
H11	0.2191	−0.3106	0.8998	0.080*
C4'	0.5983 (5)	0.1320 (4)	0.6634 (3)	0.0704 (11)
C6	0.3070 (5)	0.1658 (3)	1.1221 (2)	0.0633 (10)
H6	0.3202	0.1102	1.1610	0.076*
C7'	0.6514 (5)	0.4589 (3)	0.5922 (2)	0.0577 (10)
C14'	0.9381 (5)	0.6015 (3)	0.3042 (3)	0.0681 (11)
H14'	0.9827	0.5518	0.2621	0.082*
N1'	0.7310 (6)	0.0637 (3)	0.5286 (3)	0.0868 (11)
C13'	0.9395 (5)	0.7127 (4)	0.2952 (3)	0.0708 (11)
C5	0.3194 (5)	0.2702 (4)	1.1411 (2)	0.0697 (11)
H5	0.3415	0.2846	1.1929	0.084*
C8	0.2493 (5)	−0.1640 (3)	1.0153 (2)	0.0597 (10)
H8	0.2477	−0.2391	1.0214	0.072*
C12'	0.8791 (6)	0.7851 (3)	0.3577 (3)	0.0791 (13)
H12'	0.8836	0.8598	0.3512	0.095*
O2'	0.6821 (5)	0.0812 (3)	0.4624 (2)	0.1199 (13)
C11'	0.8114 (5)	0.7484 (3)	0.4306 (3)	0.0734 (12)
H11'	0.7713	0.7980	0.4731	0.088*
O1'	0.8319 (6)	−0.0236 (3)	0.5481 (2)	0.1366 (15)
O2	0.3185 (6)	0.3817 (3)	0.8786 (2)	0.1309 (15)
C8'	0.6340 (6)	0.6561 (3)	0.5786 (3)	0.0785 (12)
H8'	0.6164	0.7332	0.5819	0.094*
O1	0.1819 (6)	0.5084 (3)	0.9591 (2)	0.1363 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0729 (7)	0.0615 (7)	0.0633 (7)	−0.0124 (5)	−0.0007 (5)	0.0185 (5)
S1'	0.0982 (9)	0.0881 (9)	0.0658 (7)	−0.0012 (7)	−0.0043 (6)	−0.0207 (6)
Cl2'	0.0947 (9)	0.0892 (8)	0.1212 (10)	−0.0332 (7)	−0.0096 (7)	0.0432 (8)
Cl2	0.1247 (10)	0.0670 (7)	0.0990 (9)	−0.0185 (7)	−0.0239 (8)	−0.0217 (6)
Cl1'	0.1280 (11)	0.1157 (10)	0.1013 (10)	−0.0510 (9)	−0.0264 (8)	0.0499 (8)
Cl1	0.1490 (12)	0.0793 (8)	0.1167 (11)	−0.0433 (8)	−0.0024 (9)	−0.0282 (7)
N2	0.0489 (18)	0.0452 (18)	0.057 (2)	−0.0088 (14)	−0.0001 (15)	0.0068 (15)
N2'	0.0536 (19)	0.056 (2)	0.058 (2)	−0.0087 (15)	−0.0144 (16)	−0.0017 (16)
C1	0.041 (2)	0.052 (2)	0.048 (2)	−0.0085 (17)	0.0027 (16)	0.0034 (18)
C9	0.038 (2)	0.045 (2)	0.063 (3)	−0.0075 (17)	0.0035 (17)	0.0139 (19)
C10'	0.050 (2)	0.050 (2)	0.073 (3)	−0.0085 (18)	−0.022 (2)	0.001 (2)
C1'	0.046 (2)	0.082 (3)	0.038 (2)	−0.008 (2)	−0.0140 (17)	0.002 (2)
C2	0.054 (2)	0.053 (2)	0.049 (2)	−0.0172 (18)	−0.0032 (17)	0.0029 (19)
C10	0.047 (2)	0.043 (2)	0.060 (2)	−0.0117 (17)	0.0071 (18)	0.0029 (19)
C7	0.041 (2)	0.054 (2)	0.051 (2)	−0.0083 (17)	0.0048 (17)	0.0083 (18)
C9'	0.054 (2)	0.053 (3)	0.067 (3)	−0.0032 (19)	−0.021 (2)	−0.013 (2)
C3	0.051 (2)	0.055 (2)	0.057 (3)	−0.0135 (18)	0.0016 (18)	0.011 (2)
N1	0.105 (3)	0.057 (3)	0.082 (3)	−0.028 (2)	0.002 (2)	0.004 (2)
C3'	0.060 (3)	0.074 (3)	0.055 (3)	−0.015 (2)	−0.010 (2)	0.009 (2)
C2'	0.050 (2)	0.073 (3)	0.047 (2)	−0.010 (2)	−0.0025 (18)	0.009 (2)
C4	0.058 (2)	0.063 (3)	0.072 (3)	−0.014 (2)	0.008 (2)	−0.012 (2)
C12	0.068 (3)	0.044 (2)	0.097 (3)	−0.016 (2)	0.000 (2)	−0.008 (2)
C15'	0.062 (3)	0.044 (2)	0.083 (3)	−0.0150 (19)	−0.011 (2)	0.005 (2)
C13	0.063 (3)	0.052 (3)	0.079 (3)	−0.010 (2)	0.002 (2)	−0.007 (2)
C6'	0.067 (3)	0.095 (3)	0.054 (3)	−0.011 (2)	−0.014 (2)	0.004 (2)
C5'	0.070 (3)	0.116 (4)	0.046 (3)	−0.022 (3)	−0.009 (2)	0.023 (3)
C15	0.078 (3)	0.044 (2)	0.064 (3)	−0.021 (2)	0.005 (2)	0.000 (2)
C14	0.098 (3)	0.046 (2)	0.065 (3)	−0.021 (2)	−0.001 (2)	−0.003 (2)
C11	0.062 (3)	0.048 (2)	0.087 (3)	−0.0114 (19)	−0.004 (2)	0.008 (2)
C4'	0.064 (3)	0.086 (3)	0.066 (3)	−0.022 (2)	−0.021 (2)	0.025 (3)
C6	0.068 (3)	0.065 (3)	0.056 (3)	−0.016 (2)	−0.003 (2)	0.010 (2)
C7'	0.049 (2)	0.066 (3)	0.056 (3)	−0.0033 (19)	−0.0160 (19)	−0.003 (2)
C14'	0.065 (3)	0.054 (3)	0.085 (3)	−0.018 (2)	−0.004 (2)	0.010 (2)
N1'	0.108 (3)	0.070 (3)	0.082 (3)	−0.021 (2)	−0.009 (3)	0.006 (3)
C13'	0.053 (3)	0.062 (3)	0.099 (3)	−0.013 (2)	−0.015 (2)	0.007 (3)
C5	0.074 (3)	0.082 (3)	0.053 (3)	−0.019 (2)	−0.003 (2)	−0.008 (2)
C8	0.060 (2)	0.045 (2)	0.072 (3)	−0.0136 (18)	0.004 (2)	0.007 (2)
C12'	0.069 (3)	0.049 (3)	0.127 (4)	−0.022 (2)	−0.030 (3)	0.020 (3)
O2'	0.169 (4)	0.100 (3)	0.089 (3)	−0.018 (2)	−0.032 (2)	−0.013 (2)
C11'	0.074 (3)	0.051 (3)	0.099 (4)	−0.012 (2)	−0.029 (3)	−0.008 (2)
O1'	0.181 (4)	0.076 (2)	0.131 (3)	0.013 (2)	−0.015 (3)	0.011 (2)
O2	0.237 (5)	0.094 (3)	0.074 (2)	−0.070 (3)	−0.002 (3)	0.011 (2)
C8'	0.093 (3)	0.061 (3)	0.082 (3)	−0.012 (2)	−0.023 (3)	−0.007 (2)
O1	0.185 (4)	0.066 (2)	0.143 (3)	−0.014 (2)	0.011 (3)	0.028 (2)

Geometric parameters (Å, º) top

S1—C8	1.692 (4)	C3'—C4'	1.377 (5)
S1—C7	1.730 (3)	C3'—C2'	1.378 (5)
S1'—C8'	1.695 (4)	C3'—N1'	1.459 (5)
S1'—C7'	1.737 (4)	C2'—H2'	0.9300
Cl2'—C13'	1.733 (4)	C4—C5	1.373 (5)
Cl2—C13	1.727 (4)	C12—C13	1.379 (5)
Cl1'—C4'	1.726 (4)	C12—C11	1.380 (5)
Cl1—C4	1.723 (4)	C12—H12	0.9300
N2—C7	1.300 (4)	C15'—C14'	1.380 (5)
N2—C9	1.372 (4)	C15'—H15'	0.9300
N2'—C7'	1.288 (4)	C13—C14	1.366 (5)
N2'—C9'	1.385 (4)	C6'—C5'	1.370 (5)
C1—C2	1.372 (4)	C6'—H6'	0.9300
C1—C6	1.380 (5)	C5'—C4'	1.376 (5)
C1—C7	1.468 (5)	C5'—H5'	0.9300
C9—C8	1.361 (5)	C15—C14	1.371 (5)
C9—C10	1.467 (5)	C15—H15	0.9300
C10'—C15'	1.372 (5)	C14—H14	0.9300
C10'—C11'	1.402 (5)	C11—H11	0.9300
C10'—C9'	1.465 (5)	C6—C5	1.357 (5)
C1'—C2'	1.383 (5)	C6—H6	0.9300
C1'—C6'	1.396 (5)	C14'—C13'	1.374 (5)
C1'—C7'	1.458 (5)	C14'—H14'	0.9300
C2—C3	1.372 (4)	N1'—O2'	1.205 (4)
C2—H2	0.9300	N1'—O1'	1.219 (4)
C10—C15	1.380 (5)	C13'—C12'	1.366 (5)
C10—C11	1.388 (5)	C5—H5	0.9300
C9'—C8'	1.352 (5)	C8—H8	0.9300
C3—C4	1.395 (5)	C12'—C11'	1.382 (5)
C3—N1	1.464 (5)	C12'—H12'	0.9300
N1—O1	1.193 (4)	C11'—H11'	0.9300
N1—O2	1.195 (4)	C8'—H8'	0.9300

C8—S1—C7	89.27 (18)	C14—C13—Cl2	119.9 (3)
C8'—S1'—C7'	89.0 (2)	C12—C13—Cl2	119.5 (3)
C7—N2—C9	111.8 (3)	C5'—C6'—C1'	121.2 (4)
C7'—N2'—C9'	112.2 (3)	C5'—C6'—H6'	119.4
C2—C1—C6	118.2 (3)	C1'—C6'—H6'	119.4
C2—C1—C7	119.1 (3)	C6'—C5'—C4'	121.1 (4)
C6—C1—C7	122.7 (3)	C6'—C5'—H5'	119.4
C8—C9—N2	113.8 (3)	C4'—C5'—H5'	119.4
C8—C9—C10	126.9 (3)	C14—C15—C10	122.0 (4)
N2—C9—C10	119.3 (3)	C14—C15—H15	119.0
C15'—C10'—C11'	118.2 (4)	C10—C15—H15	119.0
C15'—C10'—C9'	120.1 (3)	C13—C14—C15	119.5 (4)
C11'—C10'—C9'	121.7 (4)	C13—C14—H14	120.2
C2'—C1'—C6'	117.4 (4)	C15—C14—H14	120.2
C2'—C1'—C7'	120.0 (3)	C12—C11—C10	121.5 (4)
C6'—C1'—C7'	122.5 (4)	C12—C11—H11	119.3
C3—C2—C1	120.9 (3)	C10—C11—H11	119.3
C3—C2—H2	119.5	C5'—C4'—C3'	118.1 (4)
C1—C2—H2	119.5	C5'—C4'—Cl1'	119.0 (4)
C15—C10—C11	117.3 (4)	C3'—C4'—Cl1'	122.7 (4)
C15—C10—C9	120.3 (3)	C5—C6—C1	121.0 (4)
C11—C10—C9	122.3 (3)	C5—C6—H6	119.5
N2—C7—C1	123.5 (3)	C1—C6—H6	119.5
N2—C7—S1	113.8 (3)	N2'—C7'—C1'	124.4 (3)
C1—C7—S1	122.7 (3)	N2'—C7'—S1'	113.7 (3)
C8'—C9'—N2'	113.3 (4)	C1'—C7'—S1'	121.9 (3)
C8'—C9'—C10'	126.8 (4)	C13'—C14'—C15'	118.8 (4)
N2'—C9'—C10'	119.9 (3)	C13'—C14'—H14'	120.6
C2—C3—C4	120.6 (3)	C15'—C14'—H14'	120.6
C2—C3—N1	117.2 (3)	O2'—N1'—O1'	123.4 (4)
C4—C3—N1	122.2 (4)	O2'—N1'—C3'	118.3 (4)
O1—N1—O2	122.6 (4)	O1'—N1'—C3'	118.3 (4)
O1—N1—C3	119.8 (4)	C12'—C13'—C14'	120.7 (4)
O2—N1—C3	117.6 (4)	C12'—C13'—Cl2'	119.3 (3)
C4'—C3'—C2'	121.3 (4)	C14'—C13'—Cl2'	120.0 (4)
C4'—C3'—N1'	120.5 (4)	C6—C5—C4	121.7 (4)
C2'—C3'—N1'	118.2 (4)	C6—C5—H5	119.2
C3'—C2'—C1'	120.9 (4)	C4—C5—H5	119.2
C3'—C2'—H2'	119.6	C9—C8—S1	111.3 (3)
C1'—C2'—H2'	119.6	C9—C8—H8	124.4
C5—C4—C3	117.5 (4)	S1—C8—H8	124.4
C5—C4—Cl1	119.0 (3)	C13'—C12'—C11'	120.5 (4)
C3—C4—Cl1	123.4 (3)	C13'—C12'—H12'	119.8
C13—C12—C11	119.1 (4)	C11'—C12'—H12'	119.8
C13—C12—H12	120.4	C12'—C11'—C10'	119.7 (4)
C11—C12—H12	120.4	C12'—C11'—H11'	120.1
C10'—C15'—C14'	122.1 (4)	C10'—C11'—H11'	120.1
C10'—C15'—H15'	119.0	C9'—C8'—S1'	111.7 (3)
C14'—C15'—H15'	119.0	C9'—C8'—H8'	124.1
C14—C13—C12	120.5 (4)	S1'—C8'—H8'	124.1

C7—N2—C9—C8	−0.2 (4)	C9—C10—C15—C14	−175.7 (3)
C7—N2—C9—C10	178.1 (3)	C12—C13—C14—C15	−1.5 (6)
C6—C1—C2—C3	−1.1 (5)	Cl2—C13—C14—C15	176.2 (3)
C7—C1—C2—C3	−179.9 (3)	C10—C15—C14—C13	−0.5 (6)
C8—C9—C10—C15	173.0 (3)	C13—C12—C11—C10	0.3 (6)
N2—C9—C10—C15	−5.1 (5)	C15—C10—C11—C12	−2.3 (5)
C8—C9—C10—C11	−5.0 (5)	C9—C10—C11—C12	175.8 (3)
N2—C9—C10—C11	176.9 (3)	C6'—C5'—C4'—C3'	−1.1 (6)
C9—N2—C7—C1	−179.4 (3)	C6'—C5'—C4'—Cl1'	−176.4 (3)
C9—N2—C7—S1	0.2 (4)	C2'—C3'—C4'—C5'	−0.4 (5)
C2—C1—C7—N2	−0.3 (5)	N1'—C3'—C4'—C5'	−178.6 (4)
C6—C1—C7—N2	−179.2 (3)	C2'—C3'—C4'—Cl1'	174.7 (3)
C2—C1—C7—S1	−179.9 (2)	N1'—C3'—C4'—Cl1'	−3.6 (5)
C6—C1—C7—S1	1.3 (4)	C2—C1—C6—C5	0.7 (5)
C8—S1—C7—N2	−0.1 (3)	C7—C1—C6—C5	179.5 (3)
C8—S1—C7—C1	179.5 (3)	C9'—N2'—C7'—C1'	178.9 (3)
C7'—N2'—C9'—C8'	−1.1 (4)	C9'—N2'—C7'—S1'	1.0 (4)
C7'—N2'—C9'—C10'	−178.9 (3)	C2'—C1'—C7'—N2'	−6.4 (5)
C15'—C10'—C9'—C8'	−171.7 (4)	C6'—C1'—C7'—N2'	174.8 (3)
C11'—C10'—C9'—C8'	7.1 (6)	C2'—C1'—C7'—S1'	171.4 (3)
C15'—C10'—C9'—N2'	5.8 (5)	C6'—C1'—C7'—S1'	−7.5 (5)
C11'—C10'—C9'—N2'	−175.5 (3)	C8'—S1'—C7'—N2'	−0.6 (3)
C1—C2—C3—C4	0.6 (5)	C8'—S1'—C7'—C1'	−178.5 (3)
C1—C2—C3—N1	178.8 (3)	C10'—C15'—C14'—C13'	−0.2 (5)
C2—C3—N1—O1	146.7 (4)	C4'—C3'—N1'—O2'	132.4 (4)
C4—C3—N1—O1	−35.2 (6)	C2'—C3'—N1'—O2'	−45.9 (6)
C2—C3—N1—O2	−35.0 (5)	C4'—C3'—N1'—O1'	−50.1 (6)
C4—C3—N1—O2	143.1 (4)	C2'—C3'—N1'—O1'	131.7 (4)
C4'—C3'—C2'—C1'	1.2 (5)	C15'—C14'—C13'—C12'	1.9 (6)
N1'—C3'—C2'—C1'	179.5 (3)	C15'—C14'—C13'—Cl2'	−177.5 (3)
C6'—C1'—C2'—C3'	−0.5 (5)	C1—C6—C5—C4	0.2 (6)
C7'—C1'—C2'—C3'	−179.4 (3)	C3—C4—C5—C6	−0.7 (6)
C2—C3—C4—C5	0.3 (5)	Cl1—C4—C5—C6	−178.3 (3)
N1—C3—C4—C5	−177.8 (3)	N2—C9—C8—S1	0.2 (4)
C2—C3—C4—Cl1	177.7 (3)	C10—C9—C8—S1	−178.0 (3)
N1—C3—C4—Cl1	−0.3 (5)	C7—S1—C8—C9	0.0 (3)
C11'—C10'—C15'—C14'	−1.7 (5)	C14'—C13'—C12'—C11'	−1.6 (6)
C9'—C10'—C15'—C14'	177.1 (3)	Cl2'—C13'—C12'—C11'	177.8 (3)
C11—C12—C13—C14	1.6 (6)	C13'—C12'—C11'—C10'	−0.5 (6)
C11—C12—C13—Cl2	−176.1 (3)	C15'—C10'—C11'—C12'	2.1 (5)
C2'—C1'—C6'—C5'	−1.0 (5)	C9'—C10'—C11'—C12'	−176.7 (3)
C7'—C1'—C6'—C5'	177.9 (3)	N2'—C9'—C8'—S1'	0.7 (4)
C1'—C6'—C5'—C4'	1.9 (6)	C10'—C9'—C8'—S1'	178.2 (3)
C11—C10—C15—C14	2.4 (5)	C7'—S1'—C8'—C9'	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.93	2.48	3.285 (5)	145
C15′—H15′···Cl2ⁱⁱ	0.93	2.73	3.610 (4)	158

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

Experimental details

Crystal data
Chemical formula	C₁₅H₈Cl₂N₂O₂S
M_r	351.20
Crystal system, space group	Triclinic, P1
Temperature (K)	292
a, b, c (Å)	7.4379 (19), 12.305 (3), 16.808 (4)
α, β, γ (°)	88.596 (5), 84.131 (4), 76.721 (5)
V (Å³)	1489.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.28 × 0.24 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.854, 0.918
No. of measured, independent and observed [I > 2σ(I)] reflections	14507, 5235, 2855
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.130, 0.97
No. of reflections	5235
No. of parameters	397
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.21

Computer programs: SMART (Bruker, 2004), SAINT (Bruker, 2004), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1ⁱ	0.9300	2.4800	3.285 (5)	145
C15'—H15'···Cl2ⁱⁱ	0.9300	2.7300	3.610 (4)	158

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

Acknowledgements

We thank the DST–IRHPA for the CCD X-ray facility at IISc and SKN thanks the CSIR (SRF), India, for financial support.

References

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