3-Chloro-4-[2-(4-chloro­benzyl­idene)hydrazinyl­idene]-1-methyl-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Ahmad, S.; Shafiq, M.; Tahir, M.N.; Harrison, W.T.A.; Khan, I.U.

doi:10.1107/S1600536813004443

organic compounds

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ISSN: 2056-9890

Volume 69| Part 3| March 2013| Pages o422-o423

doi:10.1107/S1600536813004443

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3-Chloro-4-[2-(4-chlorobenzylidene)hydrazinylidene]-1-methyl-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Saeed Ahmad,^a Muhammad Shafiq,^b ^* M. Nawaz Tahir,^c William T. A. Harrison ^d and Islam Ullah Khan ^e

^aDepartment of Chemistry, Gomal University, Dera Ismail Khan, NWFP, Pakistan, ^bDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, ^cDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^dDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and ^eMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 27 December 2012; accepted 14 February 2013; online 23 February 2013)

In the title compound, C₁₆H₁₃Cl₂N₃O₂S, the dihedral angle between the aromatic rings is 6.62 (2)° and the C=N—N=C torsion angle is 176.2 (4)°. The thiazine ring shows an envelope conformation, with the S atom displaced by 0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). The Cl atom is an an axial conformation and is displaced by 2.015 (6) Å from the thiazine ring plane. In the crystal, molecules are linked by C—H⋯O interactions, generating a three-dimensional network. Very weak aromatic π–π stacking interactions [centroid–centroid separations = 3.928 (2) Å] are also observed.

Related literature

For background to benzothiazines, see: Misu & Togo (2003 ); Harmata et al. (2006 ). For the synthesis and biological activity of the title compound and related materials, see: Ahmad et al. (2010a ); Shafiq et al. (2011a ). For further synthetic details, see: Shafiq et al. (2011b ). For related structures, see: Ahmad et al. (2010b ); Shafiq et al. (2011c , 2013 ).

Experimental

Crystal data

C₁₆H₁₃Cl₂N₃O₂S
M_r = 382.25
Monoclinic, P 2₁ /c
a = 12.309 (2) Å
b = 17.189 (3) Å
c = 8.1837 (13) Å
β = 101.632 (8)°
V = 1695.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 296 K
0.28 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.868, T_max = 0.931
13580 measured reflections
3319 independent reflections
1736 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.140
S = 1.00
3319 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.48	3.356 (6)	158
C12—H12⋯O2ⁱⁱ	0.93	2.59	3.419 (5)	149
C13—H13⋯O1ⁱⁱⁱ	0.93	2.50	3.293 (5)	143
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y, -z; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813004443/im2417sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813004443/im2417Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813004443/im2417Isup3.cml

checkCIF report

Comment top

Benzothiazine derivatives are versatile chiral ligands (Harmata et al., 2006) and show various biological activities (Ahmad et al., 2010a, Misu & Togo, 2003). As part of our ongoing studies in this area (Shafiq et al., 2011a,b), we now describe the synthesis and structure of the title compound, (I) (Fig. 1).

The dihedral angle between the aromatic rings C1–C6 and C11–C16 is 6.6 (2)° and the C9=N2—N3=C10 torsion angle is 176.2 (4)°. The conformation of the C1/C6/C8/C9/N1/S1 thiazine ring is an envelope, with the S atom displaced by -0.633 (6) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.037 Å). This displacement is smaller than that seen in related structures (Shafiq et al., 2013). In (I), atom C7 is displaced from the mean plane of the ring by 0.541 (7) Å and Cl1, in an axial site, is displaced by 2.015 (6) Å. Atom C8 is a stereogenic centre with an S configuration in the arbitrarily-chosen asymmetric unit. Nevertheless, crystal symmetry indicates a racemic mixture.

In the crystal, moelcules are linked by C—H···O interactions (Table 1) to generate a three-dimensional network (Fig. 2). Very weak aromatic π-π stacking interactions between the benzene rings C1—C6 and C13—C18 benzene rings [centroid-centroid separations = 3.928 (2) Å] are also observed.

Related literature top

For background to benzothiazines, see: Misu & Togo (2003); Harmata et al. (2006). For the synthesis and biological activity of the title compound and related materials, see: Ahmad et al. (2010a); Shafiq et al. (2011a). For further synthetic details, see: Shafiq et al. (2011b). For related structures, see: Ahmad et al. (2010b); Shafiq et al. (2011c, 2013).

Experimental top

The Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide (Shafiq et al., 2011c) and para-chlorobenzaldehyde was prepared using the method reported previously (Shafiq et al., 2011a). Chlorination of the Schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2011b). The crude product was re-crystallized from ethyl acetate and dichloromethane solution (1:1 v/v) to obtain yellow blocks of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Partial packing diagram of (I), showing H···O interactions as double-dashed lines and π-π stacking as open pink lines.

3-Chloro-4-[2-(4-chlorobenzylidene)hydrazinylidene]-1-methyl-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₁₆H₁₃Cl₂N₃O₂S	F(000) = 784
M_r = 382.25	D_x = 1.497 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 225 reflections
a = 12.309 (2) Å	θ = 3.7–22.3°
b = 17.189 (3) Å	µ = 0.52 mm⁻¹
c = 8.1837 (13) Å	T = 296 K
β = 101.632 (8)°	Block, yellow
V = 1695.9 (5) Å³	0.28 × 0.16 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3319 independent reflections
Radiation source: fine-focus sealed tube	1736 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −15→15
T_min = 0.868, T_max = 0.931	k = −21→21
13580 measured reflections	l = −10→9

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.047P)² + 0.7016P] where P = (F_o² + 2F_c²)/3
3319 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₆H₁₃Cl₂N₃O₂S	V = 1695.9 (5) Å³
M_r = 382.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.309 (2) Å	µ = 0.52 mm⁻¹
b = 17.189 (3) Å	T = 296 K
c = 8.1837 (13) Å	0.28 × 0.16 × 0.14 mm
β = 101.632 (8)°

Data collection top

Bruker APEXII CCD diffractometer	3319 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1736 reflections with I > 2σ(I)
T_min = 0.868, T_max = 0.931	R_int = 0.076
13580 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 1.00	Δρ_max = 0.42 e Å⁻³
3319 reflections	Δρ_min = −0.33 e Å⁻³
218 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
C1	0.2793 (4)	0.0825 (2)	0.2790 (5)	0.0443 (10)
C2	0.3546 (4)	0.0531 (2)	0.4159 (5)	0.0562 (12)
H2	0.4291	0.0496	0.4103	0.067*
C3	0.3216 (5)	0.0291 (3)	0.5591 (6)	0.0754 (16)
H3	0.3733	0.0100	0.6489	0.090*
C4	0.2111 (6)	0.0339 (3)	0.5677 (6)	0.0820 (18)
H4	0.1879	0.0176	0.6635	0.098*
C5	0.1353 (5)	0.0624 (3)	0.4352 (7)	0.0736 (15)
H5	0.0609	0.0652	0.4421	0.088*
C6	0.1678 (4)	0.0875 (2)	0.2903 (5)	0.0534 (11)
C7	−0.0133 (4)	0.1564 (3)	0.1866 (7)	0.0877 (17)
H7A	−0.0670	0.1177	0.2001	0.132*
H7B	−0.0435	0.1892	0.0936	0.132*
H7C	0.0046	0.1874	0.2861	0.132*
C8	0.2436 (3)	0.1500 (2)	−0.0046 (5)	0.0456 (10)
H8	0.2703	0.1445	−0.1090	0.055*
C9	0.3205 (3)	0.1070 (2)	0.1305 (4)	0.0402 (9)
C10	0.5527 (3)	0.1066 (2)	−0.0255 (5)	0.0460 (10)
H10	0.5968	0.0836	0.0677	0.055*
C11	0.6032 (3)	0.1273 (2)	−0.1647 (5)	0.0404 (9)
C12	0.7137 (3)	0.1108 (2)	−0.1598 (5)	0.0511 (11)
H12	0.7557	0.0875	−0.0653	0.061*
C13	0.7630 (3)	0.1285 (2)	−0.2933 (6)	0.0551 (12)
H13	0.8374	0.1172	−0.2886	0.066*
C14	0.7011 (4)	0.1626 (2)	−0.4315 (5)	0.0508 (11)
C15	0.5919 (4)	0.1809 (2)	−0.4393 (5)	0.0550 (11)
H15	0.5509	0.2047	−0.5341	0.066*
C16	0.5430 (3)	0.1640 (2)	−0.3062 (5)	0.0498 (11)
H16	0.4691	0.1772	−0.3108	0.060*
S1	0.10908 (9)	0.10838 (7)	−0.03153 (14)	0.0548 (3)
N1	0.0871 (3)	0.1183 (2)	0.1564 (5)	0.0598 (10)
N2	0.4212 (3)	0.09167 (19)	0.1225 (4)	0.0493 (9)
N3	0.4512 (3)	0.11839 (19)	−0.0247 (4)	0.0504 (9)
O1	0.0296 (2)	0.1538 (2)	−0.1431 (4)	0.0787 (10)
O2	0.1256 (2)	0.02920 (17)	−0.0680 (3)	0.0573 (8)
Cl1	0.23868 (10)	0.25052 (6)	0.04375 (17)	0.0757 (4)
Cl2	0.76214 (12)	0.18282 (8)	−0.60081 (17)	0.0859 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.059 (3)	0.038 (2)	0.039 (2)	−0.009 (2)	0.015 (2)	−0.0026 (18)
C2	0.076 (3)	0.053 (3)	0.040 (2)	−0.012 (2)	0.013 (2)	−0.004 (2)
C3	0.120 (5)	0.067 (3)	0.039 (3)	−0.023 (3)	0.016 (3)	0.000 (2)
C4	0.151 (6)	0.056 (3)	0.051 (3)	−0.026 (4)	0.050 (4)	−0.009 (3)
C5	0.100 (4)	0.058 (3)	0.080 (4)	−0.017 (3)	0.057 (3)	−0.011 (3)
C6	0.072 (3)	0.038 (2)	0.057 (3)	−0.012 (2)	0.030 (3)	−0.011 (2)
C7	0.062 (3)	0.093 (4)	0.115 (4)	0.006 (3)	0.036 (3)	−0.032 (3)
C8	0.045 (3)	0.046 (2)	0.047 (2)	−0.0027 (19)	0.012 (2)	0.0048 (19)
C9	0.048 (3)	0.035 (2)	0.039 (2)	−0.006 (2)	0.0107 (19)	−0.0015 (18)
C10	0.048 (3)	0.044 (2)	0.046 (2)	0.008 (2)	0.009 (2)	0.0055 (19)
C11	0.036 (2)	0.040 (2)	0.045 (2)	−0.0033 (18)	0.0075 (19)	−0.0003 (18)
C12	0.041 (2)	0.053 (3)	0.058 (3)	0.005 (2)	0.005 (2)	0.001 (2)
C13	0.034 (2)	0.051 (3)	0.082 (3)	−0.001 (2)	0.016 (2)	−0.008 (2)
C14	0.057 (3)	0.040 (2)	0.061 (3)	−0.004 (2)	0.026 (2)	−0.001 (2)
C15	0.055 (3)	0.054 (3)	0.058 (3)	0.004 (2)	0.018 (2)	0.010 (2)
C16	0.037 (2)	0.055 (3)	0.058 (3)	0.000 (2)	0.012 (2)	0.004 (2)
S1	0.0448 (7)	0.0606 (7)	0.0593 (7)	−0.0038 (6)	0.0111 (5)	0.0011 (6)
N1	0.053 (2)	0.064 (2)	0.071 (2)	0.002 (2)	0.032 (2)	−0.003 (2)
N2	0.053 (2)	0.058 (2)	0.0383 (19)	0.0034 (18)	0.0119 (17)	0.0118 (16)
N3	0.045 (2)	0.063 (2)	0.045 (2)	0.0035 (18)	0.0116 (16)	0.0084 (18)
O1	0.0463 (19)	0.094 (3)	0.088 (2)	0.0067 (18)	−0.0040 (18)	0.017 (2)
O2	0.0593 (19)	0.0633 (19)	0.0498 (17)	−0.0074 (16)	0.0119 (15)	−0.0139 (15)
Cl1	0.0765 (9)	0.0449 (6)	0.1015 (10)	−0.0031 (6)	0.0077 (7)	0.0103 (6)
Cl2	0.1003 (11)	0.0762 (9)	0.1001 (10)	0.0026 (8)	0.0653 (9)	0.0138 (8)

Geometric parameters (Å, º) top

C1—C6	1.396 (6)	C9—N2	1.281 (5)
C1—C2	1.397 (5)	C10—N3	1.267 (5)
C1—C9	1.470 (5)	C10—C11	1.448 (5)
C2—C3	1.378 (6)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.381 (5)
C3—C4	1.379 (7)	C11—C16	1.394 (5)
C3—H3	0.9300	C12—C13	1.387 (6)
C4—C5	1.371 (7)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.363 (5)
C5—C6	1.394 (6)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.369 (5)
C6—N1	1.425 (5)	C14—Cl2	1.739 (4)
C7—N1	1.464 (5)	C15—C16	1.378 (5)
C7—H7A	0.9600	C15—H15	0.9300
C7—H7B	0.9600	C16—H16	0.9300
C7—H7C	0.9600	S1—O2	1.417 (3)
C8—C9	1.498 (5)	S1—O1	1.428 (3)
C8—Cl1	1.776 (4)	S1—N1	1.623 (4)
C8—S1	1.776 (4)	N2—N3	1.406 (4)
C8—H8	0.9800

C6—C1—C2	118.1 (4)	N3—C10—C11	123.0 (4)
C6—C1—C9	123.0 (4)	N3—C10—H10	118.5
C2—C1—C9	118.9 (4)	C11—C10—H10	118.5
C3—C2—C1	121.9 (5)	C12—C11—C16	118.2 (4)
C3—C2—H2	119.0	C12—C11—C10	120.2 (4)
C1—C2—H2	119.0	C16—C11—C10	121.6 (4)
C2—C3—C4	119.2 (5)	C11—C12—C13	121.1 (4)
C2—C3—H3	120.4	C11—C12—H12	119.4
C4—C3—H3	120.4	C13—C12—H12	119.4
C5—C4—C3	120.1 (5)	C14—C13—C12	119.2 (4)
C5—C4—H4	119.9	C14—C13—H13	120.4
C3—C4—H4	119.9	C12—C13—H13	120.4
C4—C5—C6	121.2 (5)	C13—C14—C15	121.1 (4)
C4—C5—H5	119.4	C13—C14—Cl2	119.2 (3)
C6—C5—H5	119.4	C15—C14—Cl2	119.6 (4)
C5—C6—C1	119.5 (5)	C14—C15—C16	119.7 (4)
C5—C6—N1	119.6 (4)	C14—C15—H15	120.1
C1—C6—N1	120.9 (4)	C16—C15—H15	120.1
N1—C7—H7A	109.5	C15—C16—C11	120.6 (4)
N1—C7—H7B	109.5	C15—C16—H16	119.7
H7A—C7—H7B	109.5	C11—C16—H16	119.7
N1—C7—H7C	109.5	O2—S1—O1	119.9 (2)
H7A—C7—H7C	109.5	O2—S1—N1	111.05 (18)
H7B—C7—H7C	109.5	O1—S1—N1	108.9 (2)
C9—C8—Cl1	111.1 (3)	O2—S1—C8	104.09 (18)
C9—C8—S1	109.1 (3)	O1—S1—C8	111.11 (19)
Cl1—C8—S1	110.3 (2)	N1—S1—C8	99.76 (19)
C9—C8—H8	108.7	C6—N1—C7	121.2 (4)
Cl1—C8—H8	108.7	C6—N1—S1	117.8 (3)
S1—C8—H8	108.7	C7—N1—S1	121.0 (3)
N2—C9—C1	118.8 (4)	C9—N2—N3	113.6 (3)
N2—C9—C8	122.5 (3)	C10—N3—N2	112.4 (3)
C1—C9—C8	118.6 (4)

C6—C1—C2—C3	0.1 (6)	C13—C14—C15—C16	−0.6 (6)
C9—C1—C2—C3	−180.0 (4)	Cl2—C14—C15—C16	179.1 (3)
C1—C2—C3—C4	0.3 (7)	C14—C15—C16—C11	−1.0 (6)
C2—C3—C4—C5	−0.3 (7)	C12—C11—C16—C15	2.1 (6)
C3—C4—C5—C6	−0.3 (7)	C10—C11—C16—C15	−178.0 (4)
C4—C5—C6—C1	0.7 (6)	C9—C8—S1—O2	−57.3 (3)
C4—C5—C6—N1	−178.7 (4)	Cl1—C8—S1—O2	−179.68 (19)
C2—C1—C6—C5	−0.6 (6)	C9—C8—S1—O1	172.3 (3)
C9—C1—C6—C5	179.5 (4)	Cl1—C8—S1—O1	49.9 (3)
C2—C1—C6—N1	178.8 (3)	C9—C8—S1—N1	57.4 (3)
C9—C1—C6—N1	−1.1 (6)	Cl1—C8—S1—N1	−64.9 (2)
C6—C1—C9—N2	−171.5 (4)	C5—C6—N1—C7	27.6 (6)
C2—C1—C9—N2	8.6 (5)	C1—C6—N1—C7	−151.8 (4)
C6—C1—C9—C8	9.5 (5)	C5—C6—N1—S1	−151.3 (3)
C2—C1—C9—C8	−170.4 (3)	C1—C6—N1—S1	29.3 (5)
Cl1—C8—C9—N2	−96.8 (4)	O2—S1—N1—C6	55.3 (3)
S1—C8—C9—N2	141.3 (3)	O1—S1—N1—C6	−170.5 (3)
Cl1—C8—C9—C1	82.1 (4)	C8—S1—N1—C6	−54.0 (3)
S1—C8—C9—C1	−39.7 (4)	O2—S1—N1—C7	−123.6 (4)
N3—C10—C11—C12	−178.1 (4)	O1—S1—N1—C7	10.6 (4)
N3—C10—C11—C16	1.9 (6)	C8—S1—N1—C7	127.1 (4)
C16—C11—C12—C13	−1.6 (6)	C1—C9—N2—N3	−179.5 (3)
C10—C11—C12—C13	178.5 (4)	C8—C9—N2—N3	−0.6 (5)
C11—C12—C13—C14	0.0 (6)	C11—C10—N3—N2	178.6 (3)
C12—C13—C14—C15	1.2 (6)	C9—N2—N3—C10	176.2 (4)
C12—C13—C14—Cl2	−178.6 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.48	3.356 (6)	158
C12—H12···O2ⁱⁱ	0.93	2.59	3.419 (5)	149
C13—H13···O1ⁱⁱⁱ	0.93	2.50	3.293 (5)	143

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃Cl₂N₃O₂S
M_r	382.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.309 (2), 17.189 (3), 8.1837 (13)
β (°)	101.632 (8)
V (Å³)	1695.9 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.52
Crystal size (mm)	0.28 × 0.16 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.868, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	13580, 3319, 1736
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.140, 1.00
No. of reflections	3319
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.33

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.48	3.356 (6)	158
C12—H12···O2ⁱⁱ	0.93	2.59	3.419 (5)	149
C13—H13···O1ⁱⁱⁱ	0.93	2.50	3.293 (5)	143

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

Acknowledgements

MS acknowledges the HEC Pakistan for providing a PhD fellowship and the UOS, Sargodha, for X-ray diffraction facility.

References

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