Crystal structure of (Z)-3-{3-(4-chloro­phen­yl)-2-[(4-chloro­phen­yl)imino]-2,3-di­hydro­thia­zol-4-yl}-2H-chromen-2-one

Kayalvizhi, M.; Vasuki, G.; Kumar, R.R.; Rao, V.R.

doi:10.1107/S1600536814024775

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1268-o1269

doi:10.1107/S1600536814024775

Open

access

Crystal structure of (Z)-3-{3-(4-chlorophenyl)-2-[(4-chlorophenyl)imino]-2,3-dihydrothiazol-4-yl}-2H-chromen-2-one

M. Kayalvizhi,^a G. Vasuki,^a ^* R. Raj Kumar ^b and V. Rajeswar Rao ^b

^aDepartment of Physics, Kunthavai Naachiar Government Arts College (W) (Autonomous), Thanjavur 613 007, Tamilnadu, India, and ^bDepartment of Chemistry, National Institute of Technology, Warangal 506 004, Telangana, India
^*Correspondence e-mail: vasuki.arasi@yahoo.com

Edited by G. Smith, Queensland University of Technology, Australia (Received 26 October 2014; accepted 11 November 2014; online 19 November 2014)

In the title compound, C₂₄H₁₄Cl₂N₂O₂S, the 2H-chromene ring system is approximately planar, with a maximum deviation of 0.025 (2) Å. The thiazole ring is almost planar, with an r.m.s. deviation of 0.0022 Å, and makes a dihedral angle of 58.52 (7)° with the chromene ring system. The chromene ring system is inclined at angles of 58.3 (1) and 55.39 (9)° with respect to the two chlorophenyl rings. The two chlorophenyl rings show significant deviation from coplanarity, with a dihedral angle between them of 47.69 (8)°. The crystal structure features C—H⋯Cl interactions extending in (100) and propagating along the a-axis direction and weak π–π interactions [centroid–centroid separation = 3.867 (2) Å].

Keywords: crystal structure; 2H-chromen-2-one; bioactivity; hydrogen bonding; π–π interactions.

CCDC reference: 1027667

1. Related literature

For the bioactivity of coumarin, see: Yusufzai et al. (2012 ). For related structures, see: Arshad, Osman, Chan et al. (2010 ); Arshad, Osman, Lam et al. (2010a ,b ). For synthetic chemistry, medicinal chemistry, photochemistry and solid-state chemistry applications of coumarin derivatives, see: Chopra et al. (2009 ). For the synthesis, see: Raj Kumar & Rajeswar Rao (2014 ).

2. Experimental

2.1. Crystal data

C₂₄H₁₄Cl₂N₂O₂S
M_r = 465.33
Monoclinic, P 2₁
a = 9.1491 (7) Å
b = 10.3099 (8) Å
c = 11.9347 (10) Å
β = 111.587 (2)°
V = 1046.80 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.44 mm⁻¹
T = 296 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.897, T_max = 1.000
15409 measured reflections
5549 independent reflections
4070 reflections with I > 2σ(I)
R_int = 0.024

2.3. Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.075
S = 1.03
5549 reflections
280 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack x determined using 1604 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter: −0.004 (19)

Data collection: APEX2 (Bruker, 2004 ); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1027667

Crystal structure: contains datablocks I, global, 206R. DOI: 10.1107/S1600536814024775/zs2320sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814024775/zs2320Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814024775/zs2320Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536814024775/zs2320Isup4.cml

checkCIF report

Comment top

Compounds containing the coumarin moiety exhibit useful and diverse biological activities (Yusufzai et al., 2012). Coumarins are an important class of organic compounds and have been extensively studied. Such molecules of vast structural diversity find useful applications in several areas of synthetic chemistry, medicinal chemistry and photochemistry. The formation of [2 + 2] cycloaddition products upon irradiation of coumarin and its derivatives has contributed immensely to the area of solid-state chemistry. Several substituted coumarin derivatives find applications in the dye industry and in the area of laser dyes based on the fact that such compounds show state dependent variations in their static dipole moments. The geometry and molecular packing patterns of several coumarins derivatives have been studied to evaluate the features of non-covalent interactions (Chopra et al., 2009). Some of the coumarin derivatives have been found to be useful in photochemotherapy, antitumour, anti-HIV therapy, anti-bacterial, anticoagulant, anti-fungal, cytotoxic activities, free radical scavengers and enzyme inhibiting agents. The related compounds whose structures have been solved by X-ray are 3-{2-[2-(diphenylmethylene)hydrazinyl]thiazol-4-yl}-2H-chromen-2-one (Arshad, Osman, Chan et al., 2010), (Z)-3-(2-{2-[1-(4-hydroxyphenyl)ethylidene]hydrazin-1-yl}-1,3-thiazol-4-yl)-2H-chromen-2-one (Arshad, Osman, Lam et al., 2010a) and 3-{2-[2-(2-fluororbenzylidene)hydrazinyl]-1,3-thiazol-4-yl}-2H-chromen-2-one (Arshad, Osman, Lam et al., 2010b). The title compound, C₂₄H₁₄Cl₂N₂O₂S, (Fig. 1), is a new derivative of dihydrothiazoyl coumarin. We present herein its crystal structure.

The 2H-chromene (O1/C1–C9/O2) ring system is approximately planar, with the maximum deviation of -0.025 (2) Å at atom O1. The thiazole ring (S1/N1/C10–C12) is almost planar with a r.m.s. deviation of 0.0022 Å and makes a dihedral angle of 58.52 (7)° with the chromene ring. The chromene ring system is inclined at angles of 58.3 (1)° and 55.39 (9)° with respect to the two chlorophenyl rings (C13–C18/Cl1) and (C19–C24/Cl2), respectively. The two chlorophenyl rings show significant deviation from coplanarity, with a dihedral angle between the two planes of 47.69 (8)°. The sum of bond angles around N1 [359.79 (5)°] indicates that atom N exhibits sp² hybridization. Torsion angles C1—C2—C10—N1 = -58.5 (4)° and C10—N1—C22—C23 = -51.8 (4)° indicate that the chromene ring and the chlorophenyl ring are substituted synclinally to the thiazole ring at atoms C2 and C22, respectively. The torsion angle C22—N1—C12—N2 [6.4 (4)°] indicates that the two chlorophenyl rings have a Z-configuration across the N1—C12 bond. In the crystal, a short intermolecular C3—H···Clⁱ contact is observed [3.282 (3) Å] [symmetry code: (i) x, y - 1, z] together with second longer C23—H···Cl1ⁱⁱ contact is observed between C23 and Cl1ⁱⁱ [3.547 (3) Å] [symmetry code: x + 1, y, z + 1] (Fig. 2). Inter-ring π—π stacking interactions between the symmetry related C4–C9 ring (centroid Cg3) and the C13–C18ⁱⁱⁱ ring (centroid Cg4), with Cg3···Cg4 = 3.867 (2) Å (symmetry code: (iii) x + 1, y, z + 1) further stabilize the crystal structure (Fig. 3).

Related literature top

For the bioactivity of coumarin, see: Yusufzai et al. (2012). For the biological applications of coumarin, see: Arshad, Osman, Chan et al. (2010); Arshad, Osman, Lam et al. (2010a,b). For synthetic chemistry, medicinal chemistry, photochemistry and solid-state chemistry applications of coumarin derivatives, see: Chopra et al. (2009). For the synthesis, see: Raj Kumar & Rajeswar Rao (2014).

Experimental top

The compound was synthesized according to the published procedure (Raj Kumar & Rajeswar Rao, 2014).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

The molecular structure of the title compound showing atom numbering, with displacement ellipsoids drawn at the 50% probability level.

Crystal packing of the title compound in the unit cell, viewed along the a axis, showing C—H···Cl interactions as dashed lines.

The partial packing of the title compound, showing the π–π interactions.

(Z)-3-{3-(4-Chlorophenyl)-2-[(4-chlorophenyl)imino]-2,3-dihydrothiazol-4-yl}-2H-chromen-2-one top

Crystal data top

C₂₄H₁₄Cl₂N₂O₂S	F(000) = 476
M_r = 465.33	D_x = 1.476 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.1491 (7) Å	Cell parameters from 5853 reflections
b = 10.3099 (8) Å	θ = 4.8–29.9°
c = 11.9347 (10) Å	µ = 0.44 mm⁻¹
β = 111.587 (2)°	T = 296 K
V = 1046.80 (14) Å³	Block, colourless
Z = 2	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	5549 independent reflections
Radiation source: fine-focus sealed tube	4070 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 30.2°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→12
T_min = 0.897, T_max = 1.000	k = −13→14
15409 measured reflections	l = −16→16

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.034	w = 1/[σ²(F_o²) + (0.0251P)² + 0.1767P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.075	(Δ/σ)_max < 0.001
S = 1.03	Δρ_max = 0.17 e Å⁻³
5549 reflections	Δρ_min = −0.20 e Å⁻³
280 parameters	Absolute structure: Flack x determined using 1604 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: −0.004 (19)

Crystal data top

C₂₄H₁₄Cl₂N₂O₂S	V = 1046.80 (14) Å³
M_r = 465.33	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.1491 (7) Å	µ = 0.44 mm⁻¹
b = 10.3099 (8) Å	T = 296 K
c = 11.9347 (10) Å	0.35 × 0.30 × 0.25 mm
β = 111.587 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5549 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	4070 reflections with I > 2σ(I)
T_min = 0.897, T_max = 1.000	R_int = 0.024
15409 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.075	Δρ_max = 0.17 e Å⁻³
S = 1.03	Δρ_min = −0.20 e Å⁻³
5549 reflections	Absolute structure: Flack x determined using 1604 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
280 parameters	Absolute structure parameter: −0.004 (19)
1 restraint

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.

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

	x	y	z	U_iso*/U_eq
Cl1	0.73427 (9)	0.67172 (10)	1.28483 (6)	0.0611 (2)
Cl2	0.07802 (15)	0.15926 (9)	0.32829 (9)	0.0911 (3)
S1	0.42551 (10)	0.84490 (8)	0.71595 (7)	0.0526 (2)
O1	0.2030 (2)	0.7096 (2)	0.17243 (18)	0.0552 (6)
O2	0.3924 (2)	0.6405 (2)	0.33588 (19)	0.0611 (6)
N1	0.3118 (2)	0.6598 (2)	0.56482 (18)	0.0408 (5)
N2	0.4358 (3)	0.5837 (2)	0.7613 (2)	0.0536 (7)
C1	0.2735 (3)	0.7030 (3)	0.2954 (2)	0.0438 (7)
C2	0.1989 (3)	0.7740 (3)	0.3656 (2)	0.0366 (6)
C3	0.0669 (3)	0.8415 (3)	0.3101 (2)	0.0386 (6)
H3	0.0194	0.8846	0.3562	0.046*
C4	−0.0030 (3)	0.8489 (3)	0.1811 (2)	0.0392 (6)
C5	−0.1396 (4)	0.9181 (3)	0.1185 (3)	0.0511 (8)
H5	−0.1912	0.9631	0.1607	0.061*
C6	−0.1983 (4)	0.9202 (4)	−0.0050 (3)	0.0606 (9)
H6	−0.2893	0.9667	−0.0465	0.073*
C7	−0.1228 (4)	0.8536 (4)	−0.0675 (3)	0.0690 (10)
H7	−0.1631	0.8562	−0.1513	0.083*
C8	0.0110 (4)	0.7834 (4)	−0.0087 (3)	0.0645 (9)
H8	0.0611	0.7378	−0.0515	0.077*
C9	0.0692 (3)	0.7822 (3)	0.1157 (2)	0.0452 (7)
C10	0.2782 (3)	0.7744 (3)	0.4978 (2)	0.0379 (6)
C11	0.3305 (4)	0.8795 (3)	0.5646 (3)	0.0462 (7)
H11	0.3174	0.9632	0.5333	0.055*
C12	0.3931 (3)	0.6762 (3)	0.6869 (2)	0.0428 (6)
C13	0.5081 (3)	0.6096 (3)	0.8852 (3)	0.0453 (7)
C14	0.6503 (4)	0.5525 (3)	0.9501 (3)	0.0551 (8)
H14	0.6992	0.5005	0.9106	0.066*
C15	0.7211 (4)	0.5712 (3)	1.0723 (3)	0.0559 (9)
H15	0.8178	0.5330	1.1149	0.067*
C16	0.6480 (3)	0.6468 (3)	1.1310 (2)	0.0422 (6)
C17	0.5071 (3)	0.7039 (3)	1.0692 (3)	0.0531 (8)
H17	0.4584	0.7554	1.1092	0.064*
C18	0.4369 (3)	0.6845 (4)	0.9460 (3)	0.0556 (8)
H18	0.3402	0.7227	0.9036	0.067*
C19	0.1469 (4)	0.3047 (3)	0.4032 (3)	0.0506 (8)
C20	0.3036 (4)	0.3174 (3)	0.4712 (3)	0.0536 (8)
H20	0.3723	0.2485	0.4792	0.064*
C21	0.3576 (4)	0.4336 (3)	0.5275 (3)	0.0492 (8)
H21	0.4636	0.4437	0.5745	0.059*
C22	0.2553 (3)	0.5348 (3)	0.5145 (2)	0.0377 (6)
C23	0.0977 (3)	0.5194 (3)	0.4499 (3)	0.0443 (7)
H23	0.0285	0.5871	0.4448	0.053*
C24	0.0419 (4)	0.4032 (3)	0.3925 (3)	0.0527 (8)
H24	−0.0645	0.3920	0.3476	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0589 (4)	0.0805 (6)	0.0361 (4)	−0.0094 (4)	0.0086 (3)	0.0030 (4)
Cl2	0.1509 (9)	0.0438 (4)	0.0690 (6)	−0.0333 (6)	0.0292 (6)	−0.0135 (5)
S1	0.0634 (5)	0.0460 (4)	0.0382 (4)	−0.0074 (4)	0.0069 (3)	−0.0095 (3)
O1	0.0514 (11)	0.0756 (15)	0.0401 (11)	0.0026 (11)	0.0187 (10)	−0.0100 (10)
O2	0.0481 (12)	0.0787 (17)	0.0577 (13)	0.0119 (12)	0.0209 (10)	−0.0019 (12)
N1	0.0441 (12)	0.0374 (11)	0.0330 (11)	−0.0043 (11)	0.0050 (9)	−0.0020 (11)
N2	0.0641 (17)	0.0458 (15)	0.0380 (13)	−0.0036 (12)	0.0037 (12)	−0.0006 (11)
C1	0.0427 (15)	0.0492 (16)	0.0404 (15)	−0.0036 (14)	0.0162 (13)	−0.0047 (13)
C2	0.0404 (15)	0.0341 (13)	0.0357 (14)	−0.0053 (12)	0.0144 (12)	−0.0038 (11)
C3	0.0476 (15)	0.0300 (12)	0.0390 (14)	−0.0045 (13)	0.0170 (12)	−0.0054 (12)
C4	0.0445 (14)	0.0337 (13)	0.0367 (13)	−0.0076 (13)	0.0117 (12)	−0.0020 (12)
C5	0.0561 (19)	0.0434 (16)	0.0460 (17)	0.0003 (14)	0.0096 (15)	0.0001 (14)
C6	0.063 (2)	0.058 (2)	0.0460 (18)	0.0005 (17)	0.0026 (16)	0.0053 (16)
C7	0.078 (2)	0.082 (2)	0.0355 (16)	−0.005 (2)	0.0079 (17)	0.0021 (19)
C8	0.066 (2)	0.088 (3)	0.0402 (17)	−0.007 (2)	0.0208 (16)	−0.0091 (18)
C9	0.0461 (16)	0.0518 (17)	0.0372 (15)	−0.0077 (14)	0.0146 (13)	−0.0026 (13)
C10	0.0371 (14)	0.0396 (15)	0.0352 (14)	−0.0007 (12)	0.0112 (12)	−0.0027 (12)
C11	0.0566 (19)	0.0402 (17)	0.0398 (16)	−0.0039 (13)	0.0154 (14)	−0.0043 (12)
C12	0.0399 (13)	0.0471 (17)	0.0370 (14)	−0.0047 (14)	0.0090 (11)	−0.0071 (14)
C13	0.0475 (16)	0.0430 (15)	0.0381 (15)	−0.0052 (13)	0.0069 (13)	0.0019 (13)
C14	0.066 (2)	0.0477 (17)	0.0456 (17)	0.0145 (16)	0.0142 (16)	0.0030 (14)
C15	0.0490 (18)	0.061 (2)	0.0464 (18)	0.0120 (15)	0.0039 (15)	0.0077 (15)
C16	0.0402 (14)	0.0489 (16)	0.0332 (13)	−0.0061 (13)	0.0086 (11)	0.0064 (13)
C17	0.0462 (16)	0.072 (2)	0.0430 (16)	0.0079 (16)	0.0182 (13)	0.0052 (15)
C18	0.0384 (14)	0.081 (2)	0.0429 (16)	0.0096 (17)	0.0095 (13)	0.0070 (18)
C19	0.079 (2)	0.0358 (15)	0.0362 (15)	−0.0115 (15)	0.0207 (15)	−0.0025 (12)
C20	0.072 (2)	0.0378 (17)	0.0506 (18)	0.0081 (14)	0.0218 (17)	0.0017 (13)
C21	0.0434 (17)	0.0474 (18)	0.0496 (18)	0.0029 (14)	0.0089 (14)	−0.0011 (14)
C22	0.0441 (16)	0.0356 (14)	0.0315 (13)	−0.0028 (12)	0.0118 (12)	−0.0021 (11)
C23	0.0390 (15)	0.0445 (17)	0.0459 (16)	−0.0006 (12)	0.0114 (13)	−0.0011 (13)
C24	0.0486 (17)	0.0565 (19)	0.0447 (17)	−0.0186 (16)	0.0075 (14)	0.0003 (15)

Geometric parameters (Å, º) top

Cl1—C16	1.731 (3)	C8—C9	1.380 (4)
Cl2—C19	1.741 (3)	C8—H8	0.9300
S1—C11	1.729 (3)	C10—C11	1.326 (4)
S1—C12	1.777 (3)	C11—H11	0.9300
O1—C1	1.371 (3)	C13—C18	1.376 (4)
O1—C9	1.382 (4)	C13—C14	1.378 (4)
O2—C1	1.203 (3)	C14—C15	1.374 (4)
N1—C12	1.381 (3)	C14—H14	0.9300
N1—C10	1.396 (4)	C15—C16	1.375 (4)
N1—C22	1.436 (3)	C15—H15	0.9300
N2—C12	1.263 (4)	C16—C17	1.362 (4)
N2—C13	1.406 (4)	C17—C18	1.386 (4)
C1—C2	1.457 (4)	C17—H17	0.9300
C2—C3	1.339 (4)	C18—H18	0.9300
C2—C10	1.474 (4)	C19—C20	1.369 (5)
C3—C4	1.435 (3)	C19—C24	1.371 (5)
C3—H3	0.9300	C20—C21	1.373 (4)
C4—C9	1.378 (4)	C20—H20	0.9300
C4—C5	1.394 (4)	C21—C22	1.371 (4)
C5—C6	1.371 (4)	C21—H21	0.9300
C5—H5	0.9300	C22—C23	1.371 (4)
C6—C7	1.372 (5)	C23—C24	1.381 (4)
C6—H6	0.9300	C23—H23	0.9300
C7—C8	1.372 (5)	C24—H24	0.9300
C7—H7	0.9300

C11—S1—C12	90.84 (13)	N2—C12—N1	123.8 (3)
C1—O1—C9	122.3 (2)	N2—C12—S1	128.0 (2)
C12—N1—C10	114.9 (2)	N1—C12—S1	108.2 (2)
C12—N1—C22	121.5 (2)	C18—C13—C14	118.4 (3)
C10—N1—C22	123.41 (19)	C18—C13—N2	122.1 (3)
C12—N2—C13	120.0 (3)	C14—C13—N2	119.4 (3)
O2—C1—O1	117.1 (3)	C15—C14—C13	121.0 (3)
O2—C1—C2	125.8 (3)	C15—C14—H14	119.5
O1—C1—C2	117.1 (2)	C13—C14—H14	119.5
C3—C2—C1	120.3 (2)	C14—C15—C16	119.5 (3)
C3—C2—C10	121.8 (2)	C14—C15—H15	120.2
C1—C2—C10	117.8 (2)	C16—C15—H15	120.2
C2—C3—C4	121.5 (3)	C17—C16—C15	120.7 (3)
C2—C3—H3	119.2	C17—C16—Cl1	118.8 (2)
C4—C3—H3	119.2	C15—C16—Cl1	120.5 (2)
C9—C4—C5	118.3 (3)	C16—C17—C18	119.2 (3)
C9—C4—C3	117.6 (2)	C16—C17—H17	120.4
C5—C4—C3	124.1 (3)	C18—C17—H17	120.4
C6—C5—C4	120.2 (3)	C13—C18—C17	121.1 (3)
C6—C5—H5	119.9	C13—C18—H18	119.5
C4—C5—H5	119.9	C17—C18—H18	119.5
C5—C6—C7	120.0 (3)	C20—C19—C24	121.9 (3)
C5—C6—H6	120.0	C20—C19—Cl2	119.3 (3)
C7—C6—H6	120.0	C24—C19—Cl2	118.7 (3)
C6—C7—C8	121.2 (3)	C19—C20—C21	118.9 (3)
C6—C7—H7	119.4	C19—C20—H20	120.5
C8—C7—H7	119.4	C21—C20—H20	120.5
C7—C8—C9	118.3 (3)	C22—C21—C20	120.0 (3)
C7—C8—H8	120.9	C22—C21—H21	120.0
C9—C8—H8	120.9	C20—C21—H21	120.0
C4—C9—C8	122.0 (3)	C23—C22—C21	120.6 (3)
C4—C9—O1	121.1 (2)	C23—C22—N1	118.7 (2)
C8—C9—O1	117.0 (3)	C21—C22—N1	120.7 (2)
C11—C10—N1	113.1 (2)	C22—C23—C24	120.0 (3)
C11—C10—C2	124.9 (3)	C22—C23—H23	120.0
N1—C10—C2	121.9 (2)	C24—C23—H23	120.0
C10—C11—S1	113.0 (2)	C19—C24—C23	118.5 (3)
C10—C11—H11	123.5	C19—C24—H24	120.7
S1—C11—H11	123.5	C23—C24—H24	120.7

C9—O1—C1—O2	−177.6 (3)	C13—N2—C12—N1	−175.3 (3)
C9—O1—C1—C2	1.5 (4)	C13—N2—C12—S1	5.4 (4)
O2—C1—C2—C3	179.3 (3)	C10—N1—C12—N2	−178.8 (3)
O1—C1—C2—C3	0.3 (4)	C22—N1—C12—N2	6.4 (4)
O2—C1—C2—C10	2.7 (4)	C10—N1—C12—S1	0.5 (3)
O1—C1—C2—C10	−176.4 (2)	C22—N1—C12—S1	−174.3 (2)
C1—C2—C3—C4	−1.5 (4)	C11—S1—C12—N2	178.9 (3)
C10—C2—C3—C4	175.0 (2)	C11—S1—C12—N1	−0.4 (2)
C2—C3—C4—C9	1.0 (4)	C12—N2—C13—C18	56.7 (4)
C2—C3—C4—C5	−179.7 (3)	C12—N2—C13—C14	−127.2 (3)
C9—C4—C5—C6	−0.7 (4)	C18—C13—C14—C15	−1.0 (5)
C3—C4—C5—C6	179.9 (3)	N2—C13—C14—C15	−177.2 (3)
C4—C5—C6—C7	0.2 (5)	C13—C14—C15—C16	0.8 (5)
C5—C6—C7—C8	0.5 (6)	C14—C15—C16—C17	−0.5 (5)
C6—C7—C8—C9	−0.6 (6)	C14—C15—C16—Cl1	179.9 (3)
C5—C4—C9—C8	0.6 (4)	C15—C16—C17—C18	0.4 (5)
C3—C4—C9—C8	−180.0 (3)	Cl1—C16—C17—C18	−180.0 (3)
C5—C4—C9—O1	−178.6 (3)	C14—C13—C18—C17	0.9 (5)
C3—C4—C9—O1	0.8 (4)	N2—C13—C18—C17	177.0 (3)
C7—C8—C9—C4	0.1 (5)	C16—C17—C18—C13	−0.6 (5)
C7—C8—C9—O1	179.3 (3)	C24—C19—C20—C21	−1.9 (5)
C1—O1—C9—C4	−2.0 (4)	Cl2—C19—C20—C21	178.3 (2)
C1—O1—C9—C8	178.7 (3)	C19—C20—C21—C22	−0.4 (5)
C12—N1—C10—C11	−0.4 (3)	C20—C21—C22—C23	3.0 (5)
C22—N1—C10—C11	174.3 (3)	C20—C21—C22—N1	−175.1 (3)
C12—N1—C10—C2	177.1 (2)	C12—N1—C22—C23	122.6 (3)
C22—N1—C10—C2	−8.2 (4)	C10—N1—C22—C23	−51.8 (4)
C3—C2—C10—C11	−58.0 (4)	C12—N1—C22—C21	−59.4 (4)
C1—C2—C10—C11	118.6 (3)	C10—N1—C22—C21	126.3 (3)
C3—C2—C10—N1	124.9 (3)	C21—C22—C23—C24	−3.2 (4)
C1—C2—C10—N1	−58.5 (4)	N1—C22—C23—C24	174.9 (3)
N1—C10—C11—S1	0.0 (3)	C20—C19—C24—C23	1.7 (5)
C2—C10—C11—S1	−177.3 (2)	Cl2—C19—C24—C23	−178.6 (2)
C12—S1—C11—C10	0.2 (3)	C22—C23—C24—C19	0.9 (4)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₄Cl₂N₂O₂S
M_r	465.33
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.1491 (7), 10.3099 (8), 11.9347 (10)
β (°)	111.587 (2)
V (Å³)	1046.80 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.897, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15409, 5549, 4070
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.707

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.075, 1.03
No. of reflections	5549
No. of parameters	280
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.20
Absolute structure	Flack x determined using 1604 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Absolute structure parameter	−0.004 (19)

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, IITM, Chennai 600 036, Tamilnadu, India, for the data collection.

References

Arshad, A., Osman, H., Chan, K. L., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o1788–o1789. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arshad, A., Osman, H., Lam, C. K., Quah, C. K. & Fun, H.-K. (2010a). Acta Cryst. E66, o1632–o1633. Web of Science CSD CrossRef IUCr Journals Google Scholar
Arshad, A., Osman, H., Lam, C. K., Quah, C. K. & Fun, H.-K. (2010b). Acta Cryst. E66, o1446–o1447. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chopra, D., Choudhury, A. R., Venugopala, K. N., Govender, T., Kruger, H. G., Maguire, G. E. M. & Guru Row, T. N. (2009). Acta Cryst. E65, o3047–o3048. 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
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259. Web of Science CrossRef CAS IUCr Journals Google Scholar
Raj Kumar, R. & Rajeswar Rao, V. (2014). Synth. Commun. 44, 1301–1306. 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
Yusufzai, S. K., Osman, H., Rahim, A. S. A., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o2416–o2417. CSD CrossRef CAS IUCr Journals 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.