4-[2-(Anthracen-9-yl­methyl­idene)hydrazinyl­idene]-3-chloro-1-methyl-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Tahir, M.N.; Khan, I.U.; Bokhari, T.H.; Asghar, M.N.

doi:10.1107/S1600536812021642

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1788

doi:10.1107/S1600536812021642

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4-[2-(Anthracen-9-ylmethylidene)hydrazinylidene]-3-chloro-1-methyl-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^c Tanveer Hussain Bokhari ^a and Muhammad Nadeem Asghar ^d

^aDepartment of Chemistry, Government College University, Faisalabad, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan, and ^dForman Christian College (A Chartered University), Ferozepur Road, Lahore-54600, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 6 May 2012; accepted 13 May 2012; online 19 May 2012)

In the title compound, C₂₄H₁₈ClN₃O₂S, the dihedral angle between the benzene ring and the anthracene ring system is 41.10 (8)°. The thiazine ring has a half-chair conformation and the Cl atom is in an axial orientation. In the crystal, molecules are linked by C—H⋯O interactions, generating C(8) chains along [100]. A C—H⋯N short contact occurs in the molecule, generating an S(6) ring.

Related literature

For a related structure and references to further synthetic details, see: Shafiq et al. (2012 ). For puckering parameters, see: Cremer & Pople (1975 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₂₄H₁₈ClN₃O₂S
M_r = 447.92
Monoclinic, P 2₁ /c
a = 8.5133 (4) Å
b = 19.8999 (8) Å
c = 12.7849 (6) Å
β = 105.026 (2)°
V = 2091.88 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.930, T_max = 0.960
16154 measured reflections
3788 independent reflections
2827 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.136
S = 1.04
3788 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.59	3.370 (4)	142
C22—H22⋯N3	0.93	2.29	2.913 (4)	123
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812021642/hb6779sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812021642/hb6779Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812021642/hb6779Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of thiazine derivatives (Shafiq et al., 2012), we now describe the structure of the title compound, (I), (Fig. 1).

In (I), the benzene ring A (C1—C6) and anthracene group B (C10—C23) are almost planar with r. m. s. deviation of 0.0090 and 0.0144 Å, respectively. The dihedral angle between A/B is 41.10 (8)°. The central group C (N2/N3/C9) is of course planar. The dihedral angle between A/C and B/C is 13.63 (26) and 27.48 (26)°, respectively. The thiazine ring D (C1/C6/C7/C8/S1/N1) is in the half-chair form, with the maximum puckering amplitude (Cremer & Pople, 1975), Q = 0.578 (2) Å. There exist S(6) ring motif (Bernstein et al., 1995) due to H-bonding of C—H···N type (Table 1, Fig. 1). The molecules form C(8) chains extending along the a-axis due to H-bonding of C—H···O type (Table 1, Fig. 2).

Related literature top

For a related structure and references to further synthetic details, see: Shafiq et al. (2012). For puckering parameters, see: Cremer & Pople (1975). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide and anthracene-9-carbaldehyde was prepared using the method reported previously (Shafiq et al. 2012). The chlorination of the schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2012). The crude product of (I) was re-crystallized in ethyl acetate to get orange prisms.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level. The dotted line indicates the intra-molecular short contact.
	Fig. 2. The partial packing, which shows that molecules form one-dimensional polymeric chains extending along the [100] direction.

4-[2-(Anthracen-9-ylmethylidene)hydrazinylidene]-3-chloro-1-methyl- 3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₂₄H₁₈ClN₃O₂S	F(000) = 928
M_r = 447.92	D_x = 1.422 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2827 reflections
a = 8.5133 (4) Å	θ = 2.1–25.3°
b = 19.8999 (8) Å	µ = 0.31 mm⁻¹
c = 12.7849 (6) Å	T = 296 K
β = 105.026 (2)°	Prism, orange
V = 2091.88 (16) Å³	0.26 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3788 independent reflections
Radiation source: fine-focus sealed tube	2827 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 8.10 pixels mm^-1	θ_max = 25.3°, θ_min = 2.1°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→18
T_min = 0.930, T_max = 0.960	l = −15→15
16154 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0652P)² + 0.8876P] where P = (F_o² + 2F_c²)/3
3788 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₄H₁₈ClN₃O₂S	V = 2091.88 (16) Å³
M_r = 447.92	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.5133 (4) Å	µ = 0.31 mm⁻¹
b = 19.8999 (8) Å	T = 296 K
c = 12.7849 (6) Å	0.26 × 0.22 × 0.20 mm
β = 105.026 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3788 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2827 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.960	R_int = 0.031
16154 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.136	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
3788 reflections	Δρ_min = −0.35 e Å⁻³
281 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl1	0.31773 (12)	0.02405 (4)	0.89027 (7)	0.0772 (3)
S1	0.47338 (9)	0.15552 (4)	0.89884 (6)	0.0561 (3)
O1	0.6215 (3)	0.12587 (13)	0.95945 (17)	0.0790 (8)
O2	0.4770 (2)	0.20988 (10)	0.82508 (16)	0.0625 (7)
N1	0.3657 (3)	0.17603 (12)	0.98246 (17)	0.0581 (8)
N2	0.1106 (3)	0.12240 (10)	0.66521 (16)	0.0470 (7)
N3	0.1929 (3)	0.07899 (11)	0.61082 (16)	0.0520 (8)
C1	0.1136 (3)	0.17431 (11)	0.8339 (2)	0.0436 (8)
C2	−0.0466 (3)	0.19551 (13)	0.7960 (2)	0.0533 (9)
C3	−0.1214 (4)	0.23414 (14)	0.8580 (3)	0.0632 (11)
C4	−0.0340 (4)	0.25376 (14)	0.9606 (3)	0.0665 (13)
C5	0.1253 (4)	0.23567 (14)	0.9993 (2)	0.0596 (10)
C6	0.2010 (4)	0.19540 (13)	0.9382 (2)	0.0498 (9)
C7	0.3445 (3)	0.09596 (13)	0.8164 (2)	0.0485 (8)
C8	0.1851 (3)	0.13033 (12)	0.76582 (18)	0.0414 (8)
C9	0.1181 (3)	0.07213 (12)	0.51179 (19)	0.0456 (8)
C10	0.1765 (3)	0.03012 (12)	0.43534 (19)	0.0430 (8)
C11	0.1245 (3)	0.04805 (12)	0.32402 (19)	0.0456 (8)
C12	0.0261 (4)	0.10529 (14)	0.2848 (2)	0.0619 (10)
C13	−0.0196 (4)	0.12103 (16)	0.1775 (2)	0.0676 (10)
C14	0.0306 (4)	0.08209 (16)	0.1014 (2)	0.0667 (10)
C15	0.1244 (4)	0.02818 (15)	0.1340 (2)	0.0603 (10)
C16	0.1755 (3)	0.00887 (13)	0.2453 (2)	0.0473 (8)
C17	0.2714 (3)	−0.04692 (13)	0.2787 (2)	0.0534 (10)
C18	0.3237 (3)	−0.06616 (12)	0.3865 (2)	0.0490 (9)
C19	0.4221 (4)	−0.12438 (15)	0.4175 (3)	0.0641 (11)
C20	0.4705 (4)	−0.14389 (16)	0.5208 (3)	0.0742 (13)
C21	0.4206 (4)	−0.10726 (15)	0.6017 (3)	0.0723 (11)
C22	0.3269 (4)	−0.05134 (14)	0.5762 (2)	0.0596 (10)
C23	0.2760 (3)	−0.02744 (12)	0.4675 (2)	0.0447 (8)
C24	0.4352 (5)	0.1704 (2)	1.0998 (2)	0.0851 (15)
H2	−0.10484	0.18318	0.72662	0.0639*
H3	−0.22948	0.24698	0.83144	0.0757*
H4	−0.08417	0.27945	1.00339	0.0798*
H5	0.18372	0.25048	1.06725	0.0716*
H7	0.39378	0.08215	0.75851	0.0582*
H9	0.02056	0.09509	0.48613	0.0547*
H12	−0.00791	0.13259	0.33383	0.0744*
H13	−0.08517	0.15836	0.15457	0.0813*
H14	−0.00106	0.09351	0.02836	0.0801*
H15	0.15741	0.00253	0.08271	0.0725*
H17	0.30231	−0.07276	0.22679	0.0640*
H19	0.45336	−0.14929	0.36469	0.0764*
H20	0.53679	−0.18145	0.53962	0.0887*
H21	0.45241	−0.12174	0.67323	0.0865*
H22	0.29546	−0.02823	0.63070	0.0713*
H24A	0.46719	0.21406	1.12959	0.1277*
H24B	0.52845	0.14138	1.11401	0.1277*
H24C	0.35525	0.15194	1.13268	0.1277*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1028 (7)	0.0585 (5)	0.0677 (5)	0.0011 (4)	0.0176 (5)	0.0132 (4)
S1	0.0554 (4)	0.0686 (5)	0.0428 (4)	−0.0061 (3)	0.0100 (3)	−0.0092 (3)
O1	0.0610 (13)	0.1054 (17)	0.0592 (13)	0.0087 (12)	−0.0049 (10)	−0.0130 (12)
O2	0.0646 (13)	0.0666 (12)	0.0617 (12)	−0.0183 (10)	0.0263 (10)	−0.0031 (10)
N1	0.0694 (16)	0.0683 (15)	0.0333 (12)	−0.0026 (12)	0.0076 (11)	−0.0079 (11)
N2	0.0551 (13)	0.0515 (12)	0.0352 (11)	0.0019 (10)	0.0131 (10)	−0.0046 (9)
N3	0.0600 (14)	0.0615 (13)	0.0347 (12)	0.0041 (11)	0.0127 (10)	−0.0103 (10)
C1	0.0547 (16)	0.0401 (13)	0.0410 (14)	−0.0090 (11)	0.0215 (12)	−0.0026 (11)
C2	0.0561 (17)	0.0506 (15)	0.0574 (17)	−0.0084 (13)	0.0225 (14)	−0.0053 (13)
C3	0.0625 (19)	0.0526 (16)	0.085 (2)	−0.0038 (14)	0.0378 (17)	−0.0041 (16)
C4	0.095 (3)	0.0477 (16)	0.075 (2)	−0.0053 (16)	0.055 (2)	−0.0096 (15)
C5	0.091 (2)	0.0487 (16)	0.0480 (16)	−0.0079 (15)	0.0339 (16)	−0.0090 (13)
C6	0.0706 (19)	0.0436 (14)	0.0406 (14)	−0.0100 (13)	0.0239 (13)	−0.0041 (11)
C7	0.0562 (16)	0.0547 (15)	0.0354 (13)	−0.0003 (12)	0.0132 (12)	−0.0057 (11)
C8	0.0504 (15)	0.0433 (13)	0.0330 (13)	−0.0080 (11)	0.0152 (11)	−0.0037 (10)
C9	0.0561 (16)	0.0464 (14)	0.0343 (13)	−0.0019 (12)	0.0120 (12)	−0.0022 (11)
C10	0.0514 (15)	0.0441 (13)	0.0337 (13)	−0.0074 (11)	0.0114 (11)	−0.0054 (10)
C11	0.0569 (16)	0.0455 (14)	0.0335 (13)	−0.0095 (12)	0.0103 (11)	−0.0059 (11)
C12	0.089 (2)	0.0559 (16)	0.0392 (15)	0.0073 (15)	0.0136 (14)	−0.0011 (13)
C13	0.094 (2)	0.0603 (17)	0.0434 (16)	0.0009 (16)	0.0084 (16)	0.0050 (14)
C14	0.096 (2)	0.0651 (19)	0.0341 (15)	−0.0196 (18)	0.0083 (15)	0.0018 (14)
C15	0.083 (2)	0.0653 (18)	0.0354 (14)	−0.0200 (16)	0.0202 (14)	−0.0123 (13)
C16	0.0590 (16)	0.0473 (14)	0.0371 (13)	−0.0133 (12)	0.0154 (12)	−0.0083 (11)
C17	0.0653 (18)	0.0554 (16)	0.0461 (16)	−0.0120 (14)	0.0265 (13)	−0.0138 (13)
C18	0.0510 (16)	0.0436 (14)	0.0555 (17)	−0.0076 (12)	0.0192 (13)	−0.0077 (12)
C19	0.072 (2)	0.0532 (16)	0.073 (2)	0.0051 (15)	0.0296 (17)	−0.0012 (15)
C20	0.078 (2)	0.0541 (18)	0.090 (3)	0.0105 (16)	0.0211 (19)	0.0066 (17)
C21	0.089 (2)	0.0621 (19)	0.0595 (19)	0.0060 (17)	0.0081 (17)	0.0120 (15)
C22	0.077 (2)	0.0533 (16)	0.0454 (16)	0.0013 (14)	0.0103 (14)	0.0003 (13)
C23	0.0504 (15)	0.0436 (13)	0.0386 (13)	−0.0086 (11)	0.0086 (11)	−0.0028 (11)
C24	0.092 (3)	0.124 (3)	0.0344 (16)	−0.008 (2)	0.0078 (16)	−0.0069 (18)

Geometric parameters (Å, º) top

Cl1—C7	1.762 (3)	C16—C17	1.379 (4)
S1—O1	1.426 (3)	C17—C18	1.388 (3)
S1—O2	1.441 (2)	C18—C19	1.424 (4)
S1—N1	1.630 (3)	C18—C23	1.432 (4)
S1—C7	1.766 (3)	C19—C20	1.335 (5)
N1—C6	1.423 (4)	C20—C21	1.418 (5)
N1—C24	1.467 (3)	C21—C22	1.359 (4)
N2—N3	1.405 (3)	C22—C23	1.426 (4)
N2—C8	1.288 (3)	C2—H2	0.9300
N3—C9	1.269 (3)	C3—H3	0.9300
C1—C2	1.389 (4)	C4—H4	0.9300
C1—C6	1.412 (4)	C5—H5	0.9300
C1—C8	1.473 (3)	C7—H7	0.9800
C2—C3	1.374 (4)	C9—H9	0.9300
C3—C4	1.386 (5)	C12—H12	0.9300
C4—C5	1.366 (5)	C13—H13	0.9300
C5—C6	1.389 (4)	C14—H14	0.9300
C7—C8	1.508 (4)	C15—H15	0.9300
C9—C10	1.467 (3)	C17—H17	0.9300
C10—C11	1.422 (3)	C19—H19	0.9300
C10—C23	1.421 (3)	C20—H20	0.9300
C11—C12	1.426 (4)	C21—H21	0.9300
C11—C16	1.427 (4)	C22—H22	0.9300
C12—C13	1.362 (4)	C24—H24A	0.9600
C13—C14	1.395 (4)	C24—H24B	0.9600
C14—C15	1.338 (4)	C24—H24C	0.9600
C15—C16	1.429 (4)

O1—S1—O2	120.04 (14)	C18—C19—C20	121.3 (3)
O1—S1—N1	108.40 (13)	C19—C20—C21	119.9 (3)
O1—S1—C7	111.82 (14)	C20—C21—C22	121.0 (3)
O2—S1—N1	110.63 (12)	C21—C22—C23	121.2 (3)
O2—S1—C7	103.22 (12)	C10—C23—C18	119.0 (2)
N1—S1—C7	101.03 (13)	C10—C23—C22	124.0 (2)
S1—N1—C6	118.09 (17)	C18—C23—C22	117.0 (2)
S1—N1—C24	120.3 (2)	C1—C2—H2	119.00
C6—N1—C24	121.5 (3)	C3—C2—H2	119.00
N3—N2—C8	113.0 (2)	C2—C3—H3	120.00
N2—N3—C9	112.0 (2)	C4—C3—H3	120.00
C2—C1—C6	117.9 (2)	C3—C4—H4	120.00
C2—C1—C8	119.6 (2)	C5—C4—H4	120.00
C6—C1—C8	122.5 (2)	C4—C5—H5	120.00
C1—C2—C3	121.9 (3)	C6—C5—H5	120.00
C2—C3—C4	119.2 (3)	Cl1—C7—H7	109.00
C3—C4—C5	120.5 (3)	S1—C7—H7	109.00
C4—C5—C6	120.7 (3)	C8—C7—H7	108.00
N1—C6—C1	121.3 (2)	N3—C9—H9	118.00
N1—C6—C5	119.1 (2)	C10—C9—H9	118.00
C1—C6—C5	119.7 (3)	C11—C12—H12	119.00
Cl1—C7—S1	111.83 (14)	C13—C12—H12	119.00
Cl1—C7—C8	111.80 (18)	C12—C13—H13	120.00
S1—C7—C8	107.60 (17)	C14—C13—H13	119.00
N2—C8—C1	119.4 (2)	C13—C14—H14	120.00
N2—C8—C7	121.9 (2)	C15—C14—H14	120.00
C1—C8—C7	118.7 (2)	C14—C15—H15	119.00
N3—C9—C10	123.9 (2)	C16—C15—H15	119.00
C9—C10—C11	116.9 (2)	C16—C17—H17	119.00
C9—C10—C23	123.1 (2)	C18—C17—H17	119.00
C11—C10—C23	120.0 (2)	C18—C19—H19	119.00
C10—C11—C12	123.7 (2)	C20—C19—H19	119.00
C10—C11—C16	119.7 (2)	C19—C20—H20	120.00
C12—C11—C16	116.6 (2)	C21—C20—H20	120.00
C11—C12—C13	121.8 (3)	C20—C21—H21	119.00
C12—C13—C14	121.1 (3)	C22—C21—H21	120.00
C13—C14—C15	119.6 (2)	C21—C22—H22	119.00
C14—C15—C16	121.9 (3)	C23—C22—H22	119.00
C11—C16—C15	119.1 (2)	N1—C24—H24A	110.00
C11—C16—C17	119.1 (2)	N1—C24—H24B	110.00
C15—C16—C17	121.9 (2)	N1—C24—H24C	109.00
C16—C17—C18	122.8 (2)	H24A—C24—H24B	110.00
C17—C18—C19	121.0 (3)	H24A—C24—H24C	109.00
C17—C18—C23	119.5 (2)	H24B—C24—H24C	109.00
C19—C18—C23	119.6 (2)

O1—S1—N1—C6	−169.0 (2)	S1—C7—C8—C1	−43.3 (3)
O1—S1—N1—C24	7.3 (3)	N3—C9—C10—C11	−154.0 (3)
O2—S1—N1—C6	57.5 (2)	N3—C9—C10—C23	28.1 (4)
O2—S1—N1—C24	−126.2 (2)	C9—C10—C11—C12	2.7 (4)
C7—S1—N1—C6	−51.3 (2)	C9—C10—C11—C16	−179.4 (2)
C7—S1—N1—C24	125.0 (3)	C23—C10—C11—C12	−179.3 (3)
O1—S1—C7—Cl1	50.62 (19)	C23—C10—C11—C16	−1.3 (4)
O1—S1—C7—C8	173.77 (17)	C9—C10—C23—C18	178.5 (2)
O2—S1—C7—Cl1	−178.99 (14)	C9—C10—C23—C22	1.3 (4)
O2—S1—C7—C8	−55.85 (19)	C11—C10—C23—C18	0.7 (4)
N1—S1—C7—Cl1	−64.50 (17)	C11—C10—C23—C22	−176.6 (3)
N1—S1—C7—C8	58.64 (19)	C10—C11—C12—C13	179.3 (3)
S1—N1—C6—C1	23.8 (3)	C16—C11—C12—C13	1.3 (4)
S1—N1—C6—C5	−156.4 (2)	C10—C11—C16—C15	−179.0 (3)
C24—N1—C6—C1	−152.4 (3)	C10—C11—C16—C17	1.6 (4)
C24—N1—C6—C5	27.4 (4)	C12—C11—C16—C15	−0.9 (4)
C8—N2—N3—C9	−179.6 (2)	C12—C11—C16—C17	179.8 (3)
N3—N2—C8—C1	−179.8 (2)	C11—C12—C13—C14	−1.0 (5)
N3—N2—C8—C7	0.4 (3)	C12—C13—C14—C15	0.4 (5)
N2—N3—C9—C10	179.6 (2)	C13—C14—C15—C16	0.0 (5)
C6—C1—C2—C3	−1.9 (4)	C14—C15—C16—C11	0.3 (5)
C8—C1—C2—C3	177.1 (2)	C14—C15—C16—C17	179.6 (3)
C2—C1—C6—N1	−179.7 (2)	C11—C16—C17—C18	−1.3 (4)
C2—C1—C6—C5	0.5 (4)	C15—C16—C17—C18	179.3 (3)
C8—C1—C6—N1	1.3 (4)	C16—C17—C18—C19	179.7 (3)
C8—C1—C6—C5	−178.6 (2)	C16—C17—C18—C23	0.6 (4)
C2—C1—C8—N2	13.1 (4)	C17—C18—C19—C20	−178.8 (3)
C2—C1—C8—C7	−167.1 (2)	C23—C18—C19—C20	0.3 (5)
C6—C1—C8—N2	−167.9 (2)	C17—C18—C23—C10	−0.3 (4)
C6—C1—C8—C7	11.9 (4)	C17—C18—C23—C22	177.1 (3)
C1—C2—C3—C4	1.3 (4)	C19—C18—C23—C10	−179.4 (3)
C2—C3—C4—C5	0.8 (5)	C19—C18—C23—C22	−2.0 (4)
C3—C4—C5—C6	−2.2 (5)	C18—C19—C20—C21	1.5 (5)
C4—C5—C6—N1	−178.2 (3)	C19—C20—C21—C22	−1.6 (5)
C4—C5—C6—C1	1.6 (4)	C20—C21—C22—C23	−0.2 (5)
Cl1—C7—C8—N2	−100.3 (3)	C21—C22—C23—C10	179.2 (3)
Cl1—C7—C8—C1	79.9 (2)	C21—C22—C23—C18	1.9 (4)
S1—C7—C8—N2	136.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.59	3.370 (4)	142
C22—H22···N3	0.93	2.29	2.913 (4)	123

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₄H₁₈ClN₃O₂S
M_r	447.92
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.5133 (4), 19.8999 (8), 12.7849 (6)
β (°)	105.026 (2)
V (Å³)	2091.88 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.26 × 0.22 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.930, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	16154, 3788, 2827
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.136, 1.04
No. of reflections	3788
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.59	3.370 (4)	142
C22—H22···N3	0.93	2.29	2.913 (4)	123

Symmetry code: (i) x−1, y, z.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. The authors also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

References

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