2-(2,4-Dichloro­phen­yl)-9-phenyl-2,3-di­hydro­thieno[3,2-b]quinoline

Balamurugan, K.; Narmadha, D.; Suresh, J.; Perumal, S.; Lakshman, P.L.N.

doi:10.1107/S1600536809025380

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1783

doi:10.1107/S1600536809025380

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2-(2,4-Dichlorophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline

K. Balamurugan,^a D. Narmadha,^b J. Suresh,^b S. Perumal ^a and P. L. Nilantha Lakshman ^c ^*

^aSchool of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, ^bDepartment of Physics, The Madura College, Madurai 625 011, India, and ^cDepartment of Food Science and Technology, Faculty of Agriculture, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
^*Correspondence e-mail: nilanthalakshman@yahoo.co.uk

(Received 7 May 2009; accepted 1 July 2009; online 4 July 2009)

In the title compound, C₂₃H₁₅Cl₂NS, the quinoline system is almost planar [r.m.s. deviation = 0.013 (2) Å]. The phenyl group is disordered over two positions with site occupancies of 0.55 and 0.45, and is oriented in a nearly perpendicular configuration to the quinoline ring [the dihedral angles between the quinoline ring and the major and minor disordered components of the phenyl ring are 81.8 (2) and 71.6 (2)°, respectively]. The dihydrothiene ring adopts an envelope conformation. The dihedral angle between the chlorophenyl ring and the quinoline system is 79.32 (1)°. In the crystal weak C—H⋯π interactions occur.

Related literature

For the biological activity of quinoline derivatives, see: Kalluraya & Sreenivasa (1998 ); Maguire et al. (1994 ); Doube et al. (1998 ). For ring puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₃H₁₅Cl₂NS
M_r = 408.32
Monoclinic, P 2₁ /c
a = 11.8860 (5) Å
b = 11.5040 (5) Å
c = 14.0270 (6) Å
β = 94.297 (9)°
V = 1912.61 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.46 mm⁻¹
T = 293 K
0.19 × 0.16 × 0.11 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.917, T_max = 0.951
3917 measured reflections
3363 independent reflections
2577 reflections with I > 2σ(I)
R_int = 0.014
2 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.091
S = 1.02
3363 reflections
284 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg2ⁱ	0.93	2.92	3.818 (2)	162
C21—H21⋯Cg3ⁱⁱ	0.93	2.71	3.636 (2)	172
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg2 and Cg3 are the centroids of the N1/C2–C6 and C2/C3/C7–C10 rings, respectively.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025380/at2782sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025380/at2782Isup2.hkl

checkCIF report

Comment top

Quinoline exists as backbone in many natural products and pharmacologically important compounds. Their widerange of biological activities include antimalarial, antiasthmatic, antiinflamatory, antibacterial, antihypertensive and tyrosine kinase PDGF-RTK inhibiting agents (Kalluraya & Sreenivasa, 1998; Doube et al., 1998; Maguire et al., 1994). We report herein the synthesis and crystal structure of the title compound (I).

In the molecule of (I), (Fig. 1), the quinoline ring is planar and is oriented to the disordered phenyl ring in nearly perpendicular configuration. The dihendral angle between the major and minor components of the disordered phenyl rings is 26.6 (4)°. The dihydrothieno ring adopts envelope conformation with C18 being the flap atom. The puckering parameters are q₂ = 0.333 (2) Å and ϕ₂ = 319.7 (3)° (Cremer & Pople, 1975). The dihedral angle between the chlorophenyl ring and the quinoline ring is 79.32 (1)°.

In the crystal structure, there is no classical hydrogen bonds. The crystal packing is stabilized by two weak C—H···π interactions (Table 1; Cg2 and Cg3 refer to ring centroids of N1/C2–C6 and C2/C3/C7–C10, respectively).

Related literature top

For the biological activity of quinoline derivatives, see: Kalluraya & Sreenivasa (1998); Maguire et al. (1994); Doube et al. (1998). For ring puckering analysis, see: Cremer & Pople (1975). Cg2 and Cg3 are the centroids of the N1/C2–C6 and C2/C3/C7–C10 rings, respectively.

Experimental top

A mixture of 5-(2,4-dichlorophenyl)dihydrothiophen-3(2H)-one, (1 mmol), 2-aminobenzophenone (1 mmol) and trifluroaceticacid (1.5 mmol) was taken in a 10 ml quartz vial and placed in the Biotage microwave oven. The vial was sealed and subjected to microwave irradiation. The irradiation was programmed at (273 K, 25 W, 0 bar, Absorption level: very high) for 30 min. (After a period of 1–2 min, the temperature reached a plateau, 273 K, and remained constant). After N₂ gas jet cooling to room temperature (3 min), the reaction mixture was neutralized with NaHCO₃ and extracted in CH₂Cl₂ (2 X 5 ml), dried over MgSO₄ and concentrated in vacuo to give the crude product which was further purified either by a short column chromatography (silica gel, EtOAc-petroleumether, 2:8) to afford the corresponding pure quinoline derivative [melting point: 437–438 K, yield: 75%].

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The two disorder components of the phenyl ring of the molecule are shown, the minor component is labeled with the suffix '. the disorder parts

2-(2,4-Dichlorophenyl)-9-phenyl-2,3-dihydrothieno[3,2-b]quinoline top

Crystal data top

C₂₃H₁₅Cl₂NS	F(000) = 840
M_r = 408.32	D_x = 1.418 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.8860 (5) Å	θ = 2–25°
b = 11.5040 (5) Å	µ = 0.46 mm⁻¹
c = 14.0270 (6) Å	T = 293 K
β = 94.297 (9)°	Block, colourless
V = 1912.61 (14) Å³	0.19 × 0.16 × 0.11 mm
Z = 4

Data collection top

Nonius MACH-3 diffractometer	2577 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.014
Graphite monochromator	θ_max = 25.0°, θ_min = 2.3°
ω–2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = −1→13
T_min = 0.917, T_max = 0.951	l = −16→16
3917 measured reflections	2 standard reflections every 60 min
3363 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0458P)² + 0.5943P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3363 reflections	Δρ_max = 0.20 e Å⁻³
284 parameters	Δρ_min = −0.22 e Å⁻³
18 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0047 (10)

Crystal data top

C₂₃H₁₅Cl₂NS	V = 1912.61 (14) Å³
M_r = 408.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.8860 (5) Å	µ = 0.46 mm⁻¹
b = 11.5040 (5) Å	T = 293 K
c = 14.0270 (6) Å	0.19 × 0.16 × 0.11 mm
β = 94.297 (9)°

Data collection top

Nonius MACH-3 diffractometer	2577 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.014
T_min = 0.917, T_max = 0.951	2 standard reflections every 60 min
3917 measured reflections	intensity decay: none
3363 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	18 restraints
wR(F²) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.20 e Å⁻³
3363 reflections	Δρ_min = −0.22 e Å⁻³
284 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	Occ. (<1)
C2	0.11979 (16)	0.26004 (19)	0.25210 (14)	0.0464 (5)
C3	0.14508 (15)	0.30797 (18)	0.34454 (13)	0.0428 (4)
C4	0.21084 (15)	0.41146 (17)	0.35382 (12)	0.0405 (4)
C5	0.24702 (14)	0.45739 (17)	0.27087 (12)	0.0395 (4)
C6	0.21560 (15)	0.40461 (18)	0.18138 (12)	0.0428 (4)
C7	0.05703 (19)	0.1566 (2)	0.24282 (17)	0.0629 (6)
H7	0.0407	0.1247	0.1825	0.075*
C8	0.01978 (19)	0.1025 (2)	0.3209 (2)	0.0701 (7)
H8	−0.0219	0.0343	0.3134	0.084*
C9	0.04406 (18)	0.1493 (2)	0.41213 (18)	0.0632 (6)
H9	0.0185	0.1117	0.4651	0.076*
C10	0.10473 (17)	0.2492 (2)	0.42434 (15)	0.0521 (5)
H10	0.1199	0.2793	0.4855	0.063*
C17	0.25242 (17)	0.4742 (2)	0.09826 (14)	0.0523 (5)
H17A	0.1912	0.5235	0.0727	0.063*
H17B	0.2735	0.4225	0.0479	0.063*
C18	0.35345 (17)	0.54856 (19)	0.13425 (13)	0.0478 (5)
H18	0.3512	0.6213	0.0977	0.057*
C19	0.46829 (16)	0.49449 (17)	0.12880 (12)	0.0446 (5)
C20	0.56613 (17)	0.55995 (18)	0.14608 (14)	0.0472 (5)
C21	0.67332 (18)	0.5143 (2)	0.14224 (14)	0.0528 (5)
H21	0.7369	0.5605	0.1549	0.063*
C22	0.68341 (19)	0.3986 (2)	0.11907 (14)	0.0553 (5)
C23	0.5893 (2)	0.3301 (2)	0.10080 (15)	0.0588 (6)
H23	0.5971	0.2523	0.0847	0.071*
C24	0.48327 (19)	0.37731 (19)	0.10646 (14)	0.0524 (5)
H24	0.4202	0.3300	0.0951	0.063*
N1	0.15524 (13)	0.31025 (16)	0.17022 (11)	0.0487 (4)
Cl1	0.55600 (5)	0.70657 (5)	0.17491 (5)	0.0697 (2)
Cl2	0.81734 (6)	0.33969 (7)	0.11513 (6)	0.0859 (3)
S1	0.32820 (5)	0.58301 (5)	0.26012 (4)	0.05025 (17)
C11	0.23924 (16)	0.46862 (18)	0.44796 (13)	0.0453 (5)
C14	0.2954 (3)	0.5830 (3)	0.61987 (18)	0.0854 (9)
H14	0.312 (2)	0.624 (3)	0.678 (2)	0.102*
C12	0.1794 (7)	0.5609 (6)	0.4804 (6)	0.067 (2)	0.55
H12	0.1176	0.5866	0.4415	0.080*	0.55
C13	0.2032 (7)	0.6189 (8)	0.5661 (6)	0.085 (3)	0.55
H13	0.1581	0.6792	0.5854	0.102*	0.55
C15	0.3566 (7)	0.4863 (7)	0.5933 (7)	0.094 (3)	0.55
H15	0.4163	0.4594	0.6340	0.112*	0.55
C16	0.3298 (6)	0.4293 (8)	0.5068 (6)	0.076 (3)	0.55
H16	0.3722	0.3660	0.4890	0.091*	0.55
C12'	0.1533 (9)	0.5268 (6)	0.4904 (7)	0.055 (2)	0.45
H12'	0.0794	0.5282	0.4637	0.066*	0.45
C13'	0.1868 (8)	0.5831 (8)	0.5765 (7)	0.075 (3)	0.45
H13'	0.1319	0.6236	0.6068	0.090*	0.45
C15'	0.3783 (9)	0.5283 (9)	0.5745 (8)	0.083 (3)	0.45
H15'	0.4527	0.5289	0.6004	0.099*	0.45
C16'	0.3486 (7)	0.4717 (9)	0.4887 (7)	0.064 (3)	0.45
H16'	0.4048	0.4344	0.4574	0.077*	0.45

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0389 (10)	0.0567 (12)	0.0433 (10)	−0.0048 (9)	−0.0001 (8)	0.0028 (9)
C3	0.0359 (9)	0.0532 (12)	0.0393 (10)	0.0020 (9)	0.0028 (7)	0.0059 (9)
C4	0.0377 (9)	0.0506 (11)	0.0334 (9)	0.0059 (9)	0.0035 (7)	0.0029 (8)
C5	0.0373 (9)	0.0471 (10)	0.0340 (9)	0.0011 (8)	0.0030 (7)	0.0011 (8)
C6	0.0387 (9)	0.0563 (12)	0.0332 (9)	−0.0003 (9)	0.0017 (7)	0.0014 (9)
C7	0.0544 (13)	0.0730 (16)	0.0599 (13)	−0.0185 (12)	−0.0042 (10)	−0.0018 (12)
C8	0.0527 (13)	0.0715 (16)	0.0858 (18)	−0.0230 (12)	0.0033 (12)	0.0093 (14)
C9	0.0502 (12)	0.0736 (16)	0.0670 (15)	−0.0064 (12)	0.0114 (11)	0.0221 (12)
C10	0.0467 (11)	0.0646 (13)	0.0459 (11)	0.0017 (10)	0.0092 (9)	0.0101 (10)
C17	0.0532 (11)	0.0699 (14)	0.0339 (9)	−0.0036 (11)	0.0038 (8)	0.0064 (10)
C18	0.0537 (11)	0.0552 (12)	0.0353 (9)	−0.0033 (10)	0.0087 (8)	0.0079 (9)
C19	0.0540 (11)	0.0492 (11)	0.0314 (9)	−0.0030 (9)	0.0089 (8)	0.0074 (8)
C20	0.0554 (12)	0.0465 (11)	0.0410 (10)	−0.0023 (9)	0.0124 (9)	0.0054 (8)
C21	0.0524 (12)	0.0611 (14)	0.0461 (11)	−0.0019 (10)	0.0118 (9)	0.0094 (10)
C22	0.0631 (13)	0.0604 (14)	0.0443 (11)	0.0125 (11)	0.0168 (10)	0.0137 (10)
C23	0.0842 (17)	0.0479 (12)	0.0456 (11)	0.0063 (12)	0.0138 (11)	0.0070 (10)
C24	0.0649 (13)	0.0514 (12)	0.0416 (10)	−0.0075 (10)	0.0077 (9)	0.0049 (9)
N1	0.0466 (9)	0.0625 (11)	0.0364 (8)	−0.0067 (8)	−0.0004 (7)	−0.0022 (8)
Cl1	0.0660 (4)	0.0495 (3)	0.0953 (5)	−0.0083 (3)	0.0177 (3)	−0.0065 (3)
Cl2	0.0773 (4)	0.0853 (5)	0.0990 (5)	0.0299 (4)	0.0315 (4)	0.0238 (4)
S1	0.0578 (3)	0.0512 (3)	0.0430 (3)	−0.0080 (2)	0.0117 (2)	−0.0035 (2)
C11	0.0528 (11)	0.0530 (12)	0.0303 (9)	−0.0003 (10)	0.0046 (8)	0.0038 (9)
C14	0.132 (3)	0.085 (2)	0.0384 (13)	−0.019 (2)	0.0008 (16)	−0.0091 (14)
C12	0.086 (5)	0.047 (4)	0.064 (4)	0.013 (3)	−0.018 (3)	−0.007 (3)
C13	0.148 (7)	0.041 (5)	0.062 (5)	0.015 (4)	−0.022 (4)	−0.009 (3)
C15	0.076 (5)	0.158 (9)	0.043 (4)	0.005 (5)	−0.016 (3)	−0.007 (5)
C16	0.070 (4)	0.112 (7)	0.044 (3)	0.031 (4)	−0.003 (3)	−0.009 (4)
C12'	0.077 (5)	0.048 (5)	0.042 (3)	0.002 (4)	0.012 (3)	0.000 (3)
C13'	0.144 (8)	0.033 (5)	0.050 (4)	0.024 (4)	0.028 (5)	0.001 (3)
C15'	0.083 (5)	0.113 (7)	0.051 (6)	−0.027 (5)	−0.005 (4)	−0.012 (5)
C16'	0.060 (4)	0.088 (7)	0.044 (5)	−0.007 (4)	−0.001 (3)	−0.010 (4)

Geometric parameters (Å, º) top

C2—N1	1.379 (2)	C21—C22	1.378 (3)
C2—C7	1.405 (3)	C21—H21	0.9300
C2—C3	1.420 (3)	C22—C23	1.376 (3)
C3—C10	1.421 (3)	C22—Cl2	1.735 (2)
C3—C4	1.425 (3)	C23—C24	1.380 (3)
C4—C5	1.376 (2)	C23—H23	0.9300
C4—C11	1.491 (3)	C24—H24	0.9300
C5—C6	1.419 (3)	C11—C12	1.374 (7)
C5—S1	1.7505 (19)	C11—C16'	1.381 (8)
C6—N1	1.304 (2)	C11—C16	1.383 (7)
C6—C17	1.506 (3)	C11—C12'	1.391 (8)
C7—C8	1.362 (3)	C14—C13	1.348 (7)
C7—H7	0.9300	C14—C15'	1.366 (8)
C8—C9	1.399 (4)	C14—C13'	1.385 (8)
C8—H8	0.9300	C14—C15	1.395 (7)
C9—C10	1.361 (3)	C14—H14	0.95 (3)
C9—H9	0.9300	C12—C13	1.385 (7)
C10—H10	0.9300	C12—H12	0.9300
C17—C18	1.529 (3)	C13—H13	0.9300
C17—H17A	0.9700	C15—C16	1.395 (7)
C17—H17B	0.9700	C15—H15	0.9300
C18—C19	1.507 (3)	C16—H16	0.9300
C18—S1	1.8557 (19)	C12'—C13'	1.401 (8)
C18—H18	0.9800	C12'—H12'	0.9300
C19—C20	1.391 (3)	C13'—H13'	0.9300
C19—C24	1.398 (3)	C15'—C16'	1.391 (8)
C20—C21	1.383 (3)	C15'—H15'	0.9300
C20—Cl1	1.741 (2)	C16'—H16'	0.9300

N1—C2—C7	118.08 (18)	C22—C23—H23	120.1
N1—C2—C3	122.72 (18)	C24—C23—H23	120.1
C7—C2—C3	119.20 (18)	C23—C24—C19	121.6 (2)
C2—C3—C10	118.26 (19)	C23—C24—H24	119.2
C2—C3—C4	119.01 (16)	C19—C24—H24	119.2
C10—C3—C4	122.72 (18)	C6—N1—C2	116.63 (16)
C5—C4—C3	116.60 (16)	C5—S1—C18	92.02 (9)
C5—C4—C11	121.01 (18)	C12—C11—C16'	109.8 (7)
C3—C4—C11	122.39 (16)	C12—C11—C16	117.0 (6)
C4—C5—C6	120.37 (18)	C16'—C11—C16	25.1 (5)
C4—C5—S1	126.81 (15)	C12—C11—C12'	21.9 (5)
C6—C5—S1	112.78 (13)	C16'—C11—C12'	120.6 (7)
N1—C6—C5	124.62 (17)	C16—C11—C12'	117.7 (6)
N1—C6—C17	122.59 (17)	C12—C11—C4	123.0 (4)
C5—C6—C17	112.65 (17)	C16'—C11—C4	121.4 (5)
C8—C7—C2	121.0 (2)	C16—C11—C4	119.9 (4)
C8—C7—H7	119.5	C12'—C11—C4	117.8 (5)
C2—C7—H7	119.5	C13—C14—C15'	117.7 (7)
C7—C8—C9	120.2 (2)	C13—C14—C13'	20.3 (6)
C7—C8—H8	119.9	C15'—C14—C13'	118.5 (7)
C9—C8—H8	119.9	C13—C14—C15	120.9 (6)
C10—C9—C8	120.7 (2)	C15'—C14—C15	25.8 (6)
C10—C9—H9	119.6	C13'—C14—C15	111.8 (6)
C8—C9—H9	119.6	C13—C14—H14	116.3 (19)
C9—C10—C3	120.6 (2)	C15'—C14—H14	120.9 (19)
C9—C10—H10	119.7	C13'—C14—H14	120.5 (19)
C3—C10—H10	119.7	C15—C14—H14	122.7 (19)
C6—C17—C18	107.96 (16)	C11—C12—C13	125.6 (8)
C6—C17—H17A	110.1	C11—C12—H12	117.2
C18—C17—H17A	110.1	C13—C12—H12	117.2
C6—C17—H17B	110.1	C14—C13—C12	116.3 (8)
C18—C17—H17B	110.1	C14—C13—H13	121.9
H17A—C17—H17B	108.4	C12—C13—H13	121.9
C19—C18—C17	116.36 (18)	C14—C15—C16	121.2 (8)
C19—C18—S1	110.37 (13)	C14—C15—H15	119.4
C17—C18—S1	104.75 (12)	C16—C15—H15	119.4
C19—C18—H18	108.4	C11—C16—C15	118.8 (8)
C17—C18—H18	108.4	C11—C16—H16	120.6
S1—C18—H18	108.4	C15—C16—H16	120.6
C20—C19—C24	116.24 (19)	C11—C12'—C13'	114.9 (9)
C20—C19—C18	121.07 (18)	C11—C12'—H12'	122.5
C24—C19—C18	122.69 (18)	C13'—C12'—H12'	122.5
C21—C20—C19	123.2 (2)	C14—C13'—C12'	124.9 (9)
C21—C20—Cl1	117.18 (16)	C14—C13'—H13'	117.5
C19—C20—Cl1	119.57 (16)	C12'—C13'—H13'	117.5
C22—C21—C20	118.2 (2)	C14—C15'—C16'	118.3 (11)
C22—C21—H21	120.9	C14—C15'—H15'	120.9
C20—C21—H21	120.9	C16'—C15'—H15'	120.9
C23—C22—C21	120.9 (2)	C11—C16'—C15'	122.7 (11)
C23—C22—Cl2	120.38 (18)	C11—C16'—H16'	118.7
C21—C22—Cl2	118.75 (19)	C15'—C16'—H16'	118.7
C22—C23—C24	119.8 (2)

N1—C2—C3—C10	−179.85 (18)	C7—C2—N1—C6	−178.41 (19)
C7—C2—C3—C10	−0.5 (3)	C3—C2—N1—C6	1.0 (3)
N1—C2—C3—C4	−0.7 (3)	C4—C5—S1—C18	168.69 (17)
C7—C2—C3—C4	178.65 (19)	C6—C5—S1—C18	−13.48 (15)
C2—C3—C4—C5	−0.9 (3)	C19—C18—S1—C5	−99.75 (15)
C10—C3—C4—C5	178.20 (17)	C17—C18—S1—C5	26.24 (15)
C2—C3—C4—C11	178.78 (17)	C5—C4—C11—C12	82.4 (4)
C10—C3—C4—C11	−2.1 (3)	C3—C4—C11—C12	−97.3 (4)
C3—C4—C5—C6	2.2 (3)	C5—C4—C11—C16'	−68.1 (5)
C11—C4—C5—C6	−177.50 (17)	C3—C4—C11—C16'	112.3 (5)
C3—C4—C5—S1	179.84 (14)	C5—C4—C11—C16	−97.3 (5)
C11—C4—C5—S1	0.2 (3)	C3—C4—C11—C16	83.0 (5)
C4—C5—C6—N1	−2.1 (3)	C5—C4—C11—C12'	107.1 (4)
S1—C5—C6—N1	179.96 (16)	C3—C4—C11—C12'	−72.5 (4)
C4—C5—C6—C17	173.78 (17)	C16'—C11—C12—C13	−25.1 (9)
S1—C5—C6—C17	−4.2 (2)	C16—C11—C12—C13	1.1 (9)
N1—C2—C7—C8	179.8 (2)	C12'—C11—C12—C13	99 (2)
C3—C2—C7—C8	0.4 (3)	C4—C11—C12—C13	−178.6 (6)
C2—C7—C8—C9	−0.2 (4)	C15'—C14—C13—C12	24.1 (10)
C7—C8—C9—C10	0.1 (4)	C13'—C14—C13—C12	−74 (2)
C8—C9—C10—C3	−0.2 (3)	C15—C14—C13—C12	−5.3 (10)
C2—C3—C10—C9	0.4 (3)	C11—C12—C13—C14	2.3 (11)
C4—C3—C10—C9	−178.69 (19)	C13—C14—C15—C16	5.1 (12)
N1—C6—C17—C18	−159.49 (18)	C15'—C14—C15—C16	−85 (2)
C5—C6—C17—C18	24.6 (2)	C13'—C14—C15—C16	25.4 (11)
C6—C17—C18—C19	90.0 (2)	C12—C11—C16—C15	−1.5 (10)
C6—C17—C18—S1	−32.2 (2)	C16'—C11—C16—C15	77 (2)
C17—C18—C19—C20	170.37 (17)	C12'—C11—C16—C15	−26.2 (10)
S1—C18—C19—C20	−70.5 (2)	C4—C11—C16—C15	178.2 (6)
C17—C18—C19—C24	−9.6 (3)	C14—C15—C16—C11	−1.4 (12)
S1—C18—C19—C24	109.51 (18)	C12—C11—C12'—C13'	−67 (2)
C24—C19—C20—C21	−0.2 (3)	C16'—C11—C12'—C13'	−1.9 (9)
C18—C19—C20—C21	179.80 (17)	C16—C11—C12'—C13'	26.7 (8)
C24—C19—C20—Cl1	−179.75 (14)	C4—C11—C12'—C13'	−177.2 (5)
C18—C19—C20—Cl1	0.2 (2)	C13—C14—C13'—C12'	96 (3)
C19—C20—C21—C22	0.8 (3)	C15'—C14—C13'—C12'	2.8 (12)
Cl1—C20—C21—C22	−179.67 (15)	C15—C14—C13'—C12'	−24.8 (10)
C20—C21—C22—C23	−0.4 (3)	C11—C12'—C13'—C14	−0.6 (11)
C20—C21—C22—Cl2	−179.36 (15)	C13—C14—C15'—C16'	−25.4 (12)
C21—C22—C23—C24	−0.6 (3)	C13'—C14—C15'—C16'	−2.3 (12)
Cl2—C22—C23—C24	178.41 (15)	C15—C14—C15'—C16'	78.8 (19)
C22—C23—C24—C19	1.2 (3)	C12—C11—C16'—C15'	23.5 (10)
C20—C19—C24—C23	−0.8 (3)	C16—C11—C16'—C15'	−88 (2)
C18—C19—C24—C23	179.23 (18)	C12'—C11—C16'—C15'	2.3 (11)
C5—C6—N1—C2	0.4 (3)	C4—C11—C16'—C15'	177.4 (7)
C17—C6—N1—C2	−175.03 (18)	C14—C15'—C16'—C11	−0.1 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg2ⁱ	0.93	2.92	3.818 (2)	162
C21—H21···Cg3ⁱⁱ	0.93	2.71	3.636 (2)	172

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

Experimental details

Crystal data
Chemical formula	C₂₃H₁₅Cl₂NS
M_r	408.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.8860 (5), 11.5040 (5), 14.0270 (6)
β (°)	94.297 (9)
V (Å³)	1912.61 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
Crystal size (mm)	0.19 × 0.16 × 0.11

Data collection
Diffractometer	Nonius MACH-3 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.917, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	3917, 3363, 2577
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.091, 1.02
No. of reflections	3363
No. of parameters	284
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg2ⁱ	0.93	2.92	3.818 (2)	162
C21—H21···Cg3ⁱⁱ	0.93	2.71	3.636 (2)	172

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

Acknowledgements

JS and DN thank the Management of The Madura College, Madurai, for their constant support.

References

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