4-[5-(4-Chloro­phen­yl)-3-methyl-1H-pyrazol-1-yl]benzene­sulfonamide

Farrukh, M.A.; Mohamed, S.K.; Ahmed, M.; Marzouk, A.A.; El-Moghazy, S.M.

doi:10.1107/S1600536813002134

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 2| February 2013| Pages o295-o296

doi:10.1107/S1600536813002134

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4-[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]benzenesulfonamide

Muhammad A. Farrukh,^a Shaaban K. Mohamed,^b,^c Maqsood Ahmed,^a ^* Adel A. Marzouk ^d and Samir M. El-Moghazy ^e

^aDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, El-Minia, Egypt, ^dPharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, Egypt, and ^eFaculty of Pharmacy, Pharmaceutical Chemistry Department, Cairo University, Cairo, Egypt
^*Correspondence e-mail: maqsood.ahmed@gcu.edu.pk

(Received 13 January 2013; accepted 22 January 2013; online 26 January 2013)

In the title compound, C₁₆H₁₄ClN₃O₂S, the dihedral angle between the benzene and pyrazole rings is 52.75 (2)°, while that between the pyrazole and 4-chlorophenyl rings is 54.0 (3)°. The terminal sulfonamide group adopts an approximately tetrahedral geometry about the S atom with a C—S—N angle of 108.33 (10)°. In the crystal, pairs of N—H⋯N hydrogen bonds lead to the formation of inversion dimers. These dimers are linked via a second pair of N—H⋯N hydrogen bonds and C—H⋯O interactions, forming a two-dimensional network lying parallel to the bc plane. The two-dimensional networks are linked via C—H⋯Cl interactions, forming a three-dimensional structure.

Related literature

For the use of pyrazoles in metal-organic chemistry, see: Mukherjee (2000 ); Halcrow (2009 ). For the synthesis and pharmaceutical applications of pyrazole compounds, see, for example: Ranatunge et al. (2004 ); Szabo et al. (2008 ); Bekhit & Abdel-Aziem (2004 ); Bekhit et al. (2006 ); Rostom et al. (2003 ); Gökhan-Kelekçi et al. (2007 ); Lin et al. (2007 ); El-Moghazy et al. (2012 ); Sakya et al. (2008 ); Shen et al. (2004 ).

Experimental

Crystal data

C₁₆H₁₄ClN₃O₂S
M_r = 347.81
Monoclinic, P 2₁ /c
a = 15.878 (5) Å
b = 8.209 (5) Å
c = 12.953 (5) Å
β = 91.016 (5)°
V = 1688.1 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 296 K
0.33 × 0.32 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: analytical (SADABS; Bruker, 2009 ) T_min = 0.890, T_max = 0.938
17257 measured reflections
3462 independent reflections
2594 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.115
S = 1.03
3462 reflections
217 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.34 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
N1—H2N1⋯N3ⁱ	0.82 (2)	2.20 (2)	3.010 (3)	169 (2)
N1—H1N1⋯N3ⁱⁱ	0.84 (3)	2.33 (3)	3.157 (3)	167 (3)
C5—H5⋯O2ⁱⁱⁱ	0.93	2.48	3.169	131
C3—H3⋯Cl1^iv	0.93	2.93	3.602	130
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) -x+2, -y+1, -z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global_Publ_Block. DOI: 10.1107/S1600536813002134/sj5296sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813002134/sj5296Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813002134/sj5296Isup3.cml

checkCIF report

Comment top

Pyrazoles and related compounds are common molecules used in coordination or organometallic chemistry as bridging ligands, utilizing the ring positions of the two N atoms (Mukherjee, 2000; Halcrow, 2009). In addition, pyrazole derivatives represent an important class of biologically and pharmacologically active molecules. Several pyrazole compounds have been reported to be potential therapeutic agents for the treatment of inflammation (Ranatunge et al., 2004; Szabo et al., 2008; Bekhit & Abdel-Aziem 2004; Bekhit et al., 2006) including the marketed selective COX-2 drug, Celecoxib, that have been shown to be well tolerated with reduced gastrointestinal side effects (Sakya et al., 2008). Moreover, various substituted pyrazoles were reported to possess antitumor properties (Rostom et al., 2003; Lin et al., 2007). Other pyrazoles were used for treating Alzheimer's disease (Gökhan-Kelekçi et al., 2007) and acquired immunodeficiency syndrome (AIDS) (Shen et al., 2004; El-Moghazy et al., 2012).

The molecular assembly is built on the basis of intermolecular N—H···N type hydrogen bonds. The N3 atom on one side accepts a H1N1 atom from a neighbouring atom at a distance of 2.33 (3) Å and also accepts a H2N1 atom from a molecule on the opposite side at a distance of 2.20 (2) Å. There is a weak C–H···O type intermolecular hydrogen bond where the C5 atom donates its H atom to the O2 of the sulfonamide group at a distance of 2.48 Å and C—H—O angle of 130.8°. The molecule is also involved in the formation of a pair of weak intermolecular inversion related C3—H3···Cl1 hydrogen bonds where in one case the Cl1 atom accepts a H atom from a neighbouring molecule while in return, the C3 atom donates its H3 atom to the same molecule. The C–H···Cl distance in both cases is 2.93 Å and C—H—Cl angle is 130.0°.

Related literature top

For the use of pyrazoles in metal-organic chemistry, see: Mukherjee (2000); Halcrow (2009). For the synthesis and pharmaceutical applications of pyrazole compounds, see, for example: Ranatunge et al. (2004); Szabo et al. (2008); Bekhit & Abdel-Aziem (2004); Bekhit et al. (2006); Rostom et al. (2003); Gökhan-Kelekçi et al. (2007); Lin et al. (2007); El-Moghazy et al. (2012); Sakya et al. (2008); Shen et al. (2004).

Experimental top

A mixture of 1 mmol (197 mg) 1-(4-chlorophenyl)butane-1,3-dione, 1 mmol (224 mg) 4-hydrazinylbenzenesulfonamide hydrochloride, 82 mg sodium acetate and 60 mg glacial acetic acid in 50 ml e thanol was stirred at room temperature for 24 h. The mixture was filtered off and the filtrate was concentrated under vacuum to deposit the solid product which was collected, dried and recrystallized from ethanol to afford a very good yield (80%) of high quality crystals suitable for X-ray diffraction (498 – 499 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. An ORTEPIII diagram of the molecule showing the atom numbering scheme and thermal ellipsoids drawn at the 50% probability level.
	Fig. 2. A view of the molecular packing along the a axis.
	Fig. 3. A trimer of molecules formed by intermolecular N–H···N hydrogen bonds. Symmetry codes: (i) x, -y + 3/2, z - 1/2; (ii) -x + 1, -y + 1, -z
	Fig. 4. Image showing the intermolecular C–H···O and C–H···Cl hydrogen bonds. The H atoms not involved in any interaction have been omitted for clarity. Symmetry codes: (i) 2 - x, 1 - y, -z; (ii) x, 1/2 - y,1/2 + z]

4-[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]benzenesulfonamide top

Crystal data top

C₁₆H₁₄ClN₃O₂S	F(000) = 720
M_r = 347.81	D_x = 1.369 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 133 reflections
a = 15.878 (5) Å	θ = 2.7–26.0°
b = 8.209 (5) Å	µ = 0.36 mm⁻¹
c = 12.953 (5) Å	T = 296 K
β = 91.016 (5)°	Block, colourless
V = 1688.1 (13) Å³	0.33 × 0.32 × 0.18 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3462 independent reflections
Radiation source: fine-focus sealed tube	2594 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω and ϕ scans	θ_max = 26.4°, θ_min = 2.8°
Absorption correction: analytical (SADABS; Bruker, 2009)	h = −19→19
T_min = 0.890, T_max = 0.938	k = −10→10
17257 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0506P)² + 0.8701P] where P = (F_o² + 2F_c²)/3
3462 reflections	(Δ/σ)_max < 0.001
217 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₆H₁₄ClN₃O₂S	V = 1688.1 (13) Å³
M_r = 347.81	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.878 (5) Å	µ = 0.36 mm⁻¹
b = 8.209 (5) Å	T = 296 K
c = 12.953 (5) Å	0.33 × 0.32 × 0.18 mm
β = 91.016 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3462 independent reflections
Absorption correction: analytical (SADABS; Bruker, 2009)	2594 reflections with I > 2σ(I)
T_min = 0.890, T_max = 0.938	R_int = 0.030
17257 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.115	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.34 e Å⁻³
3462 reflections	Δρ_min = −0.33 e Å⁻³
217 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	0.62888 (4)	0.52544 (6)	−0.26035 (4)	0.03590 (16)
Cl1	1.07396 (5)	0.23198 (14)	0.03417 (10)	0.1065 (4)
O1	0.70283 (10)	0.5918 (2)	−0.30442 (11)	0.0545 (5)
N1	0.55446 (14)	0.6528 (2)	−0.27978 (14)	0.0381 (4)
N3	0.62419 (11)	0.5109 (2)	0.25734 (12)	0.0338 (4)
O2	0.59721 (12)	0.37105 (18)	−0.29389 (11)	0.0551 (5)
N2	0.68811 (10)	0.4740 (2)	0.19252 (12)	0.0327 (4)
C1	0.64780 (13)	0.5101 (2)	−0.12544 (14)	0.0316 (4)
C3	0.72856 (14)	0.5768 (3)	0.02534 (16)	0.0434 (5)
H3	0.7738	0.6306	0.0567	0.052*
C6	0.59263 (14)	0.4216 (3)	−0.06641 (15)	0.0383 (5)
H6	0.5465	0.3703	−0.0975	0.046*
C4	0.67440 (13)	0.4873 (2)	0.08368 (14)	0.0311 (4)
C11	0.83783 (14)	0.3838 (3)	0.19450 (17)	0.0467 (6)
C2	0.71592 (14)	0.5872 (3)	−0.08065 (16)	0.0429 (5)
H2	0.7532	0.6457	−0.1210	0.051*
C5	0.60608 (13)	0.4095 (3)	0.03862 (15)	0.0372 (5)
H5	0.5694	0.3493	0.0788	0.045*
C9	0.65766 (15)	0.4978 (3)	0.35195 (16)	0.0403 (5)
C10	0.60555 (18)	0.5323 (3)	0.44406 (17)	0.0550 (7)
H10A	0.5507	0.5687	0.4219	0.082*
H10B	0.6322	0.6156	0.4851	0.082*
H10C	0.6002	0.4349	0.4844	0.082*
C7	0.76017 (14)	0.4366 (3)	0.24501 (16)	0.0415 (5)
C16	0.83766 (17)	0.2553 (4)	0.1266 (3)	0.0688 (8)
H16	0.7877	0.1994	0.1130	0.083*
C8	0.74152 (15)	0.4516 (3)	0.34751 (17)	0.0506 (6)
H8	0.7781	0.4341	0.4033	0.061*
C14	0.98314 (17)	0.2900 (4)	0.0978 (3)	0.0676 (8)
C12	0.91258 (18)	0.4628 (4)	0.2135 (3)	0.0808 (10)
H12	0.9143	0.5492	0.2599	0.097*
C15	0.91033 (19)	0.2080 (4)	0.0784 (3)	0.0800 (10)
H15	0.9095	0.1204	0.0329	0.096*
C13	0.98526 (19)	0.4160 (5)	0.1648 (3)	0.0943 (12)
H13	1.0355	0.4710	0.1781	0.113*
H2N1	0.5670 (16)	0.747 (3)	−0.266 (2)	0.050 (8)*
H1N1	0.5061 (18)	0.620 (4)	−0.265 (2)	0.061 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0498 (3)	0.0367 (3)	0.0213 (2)	0.0057 (2)	0.0010 (2)	−0.0004 (2)
Cl1	0.0537 (5)	0.1252 (8)	0.1417 (9)	0.0173 (5)	0.0359 (5)	0.0154 (7)
O1	0.0500 (10)	0.0833 (12)	0.0304 (8)	0.0055 (9)	0.0090 (7)	0.0095 (8)
N1	0.0445 (12)	0.0344 (10)	0.0352 (10)	−0.0008 (9)	−0.0052 (8)	0.0011 (8)
N3	0.0408 (10)	0.0353 (9)	0.0254 (8)	0.0006 (7)	0.0019 (7)	0.0009 (7)
O2	0.0967 (14)	0.0358 (8)	0.0324 (8)	0.0054 (9)	−0.0079 (8)	−0.0078 (7)
N2	0.0359 (9)	0.0379 (9)	0.0241 (8)	−0.0004 (7)	−0.0012 (7)	0.0010 (7)
C1	0.0395 (11)	0.0323 (10)	0.0229 (9)	0.0057 (9)	0.0007 (8)	0.0003 (8)
C3	0.0409 (12)	0.0568 (14)	0.0322 (11)	−0.0150 (10)	−0.0038 (9)	0.0033 (10)
C6	0.0434 (12)	0.0406 (11)	0.0305 (10)	−0.0086 (10)	−0.0058 (9)	0.0012 (9)
C4	0.0369 (11)	0.0330 (10)	0.0235 (9)	0.0028 (8)	−0.0006 (8)	0.0011 (8)
C11	0.0370 (12)	0.0625 (15)	0.0405 (12)	0.0009 (11)	−0.0062 (10)	0.0068 (11)
C2	0.0423 (12)	0.0556 (14)	0.0309 (11)	−0.0108 (11)	0.0035 (9)	0.0075 (10)
C5	0.0419 (12)	0.0399 (11)	0.0297 (10)	−0.0081 (9)	0.0004 (9)	0.0046 (9)
C9	0.0529 (14)	0.0426 (12)	0.0255 (10)	−0.0081 (10)	−0.0005 (9)	0.0010 (9)
C10	0.0704 (17)	0.0659 (16)	0.0290 (11)	−0.0104 (13)	0.0082 (11)	−0.0044 (11)
C7	0.0388 (12)	0.0524 (13)	0.0331 (11)	−0.0018 (10)	−0.0069 (9)	0.0033 (10)
C16	0.0398 (14)	0.078 (2)	0.089 (2)	−0.0038 (13)	0.0061 (14)	−0.0206 (17)
C8	0.0510 (14)	0.0721 (17)	0.0284 (11)	−0.0033 (12)	−0.0110 (10)	0.0048 (11)
C14	0.0388 (14)	0.083 (2)	0.081 (2)	0.0101 (14)	0.0075 (14)	0.0159 (17)
C12	0.0460 (16)	0.102 (2)	0.095 (2)	−0.0116 (16)	−0.0052 (16)	−0.027 (2)
C15	0.0517 (18)	0.088 (2)	0.100 (3)	0.0071 (16)	0.0087 (17)	−0.0284 (19)
C13	0.0375 (16)	0.111 (3)	0.134 (3)	−0.0149 (17)	0.0036 (18)	−0.018 (3)

Geometric parameters (Å, º) top

S1—O1	1.4229 (17)	C11—C16	1.373 (4)
S1—O2	1.4284 (18)	C11—C7	1.471 (3)
S1—N1	1.594 (2)	C2—H2	0.9300
S1—C1	1.772 (2)	C5—H5	0.9300
Cl1—C14	1.740 (3)	C9—C8	1.387 (3)
N1—H2N1	0.82 (3)	C9—C10	1.491 (3)
N1—H1N1	0.84 (3)	C10—H10A	0.9600
N3—C9	1.331 (3)	C10—H10B	0.9600
N3—N2	1.363 (2)	C10—H10C	0.9600
N2—C7	1.356 (3)	C7—C8	1.371 (3)
N2—C4	1.427 (2)	C16—C15	1.378 (4)
C1—C2	1.373 (3)	C16—H16	0.9300
C1—C6	1.380 (3)	C8—H8	0.9300
C3—C4	1.369 (3)	C14—C13	1.351 (5)
C3—C2	1.387 (3)	C14—C15	1.357 (4)
C3—H3	0.9300	C12—C13	1.379 (4)
C6—C5	1.377 (3)	C12—H12	0.9300
C6—H6	0.9300	C15—H15	0.9300
C4—C5	1.380 (3)	C13—H13	0.9300
C11—C12	1.371 (4)

O1—S1—O2	120.40 (11)	C6—C5—H5	120.3
O1—S1—N1	107.47 (12)	C4—C5—H5	120.3
O2—S1—N1	106.13 (12)	N3—C9—C8	110.59 (19)
O1—S1—C1	107.23 (10)	N3—C9—C10	120.2 (2)
O2—S1—C1	106.82 (9)	C8—C9—C10	129.2 (2)
N1—S1—C1	108.33 (10)	C9—C10—H10A	109.5
S1—N1—H2N1	114.2 (18)	C9—C10—H10B	109.5
S1—N1—H1N1	116 (2)	H10A—C10—H10B	109.5
H2N1—N1—H1N1	118 (3)	C9—C10—H10C	109.5
C9—N3—N2	105.06 (17)	H10A—C10—H10C	109.5
C7—N2—N3	111.87 (16)	H10B—C10—H10C	109.5
C7—N2—C4	128.71 (18)	N2—C7—C8	105.7 (2)
N3—N2—C4	119.31 (16)	N2—C7—C11	123.38 (19)
C2—C1—C6	120.78 (18)	C8—C7—C11	130.8 (2)
C2—C1—S1	120.16 (16)	C11—C16—C15	121.0 (3)
C6—C1—S1	119.06 (15)	C11—C16—H16	119.5
C4—C3—C2	119.88 (19)	C15—C16—H16	119.5
C4—C3—H3	120.1	C7—C8—C9	106.77 (19)
C2—C3—H3	120.1	C7—C8—H8	126.6
C5—C6—C1	119.78 (19)	C9—C8—H8	126.6
C5—C6—H6	120.1	C13—C14—C15	120.7 (3)
C1—C6—H6	120.1	C13—C14—Cl1	120.2 (2)
C3—C4—C5	120.80 (18)	C15—C14—Cl1	119.2 (3)
C3—C4—N2	120.02 (18)	C11—C12—C13	121.0 (3)
C5—C4—N2	119.18 (18)	C11—C12—H12	119.5
C12—C11—C16	118.0 (3)	C13—C12—H12	119.5
C12—C11—C7	120.7 (2)	C14—C15—C16	119.6 (3)
C16—C11—C7	121.3 (2)	C14—C15—H15	120.2
C1—C2—C3	119.3 (2)	C16—C15—H15	120.2
C1—C2—H2	120.4	C14—C13—C12	119.7 (3)
C3—C2—H2	120.4	C14—C13—H13	120.2
C6—C5—C4	119.44 (19)	C12—C13—H13	120.2

C9—N3—N2—C7	0.7 (2)	N2—N3—C9—C10	179.11 (19)
C9—N3—N2—C4	−175.84 (17)	N3—N2—C7—C8	−0.5 (2)
O1—S1—C1—C2	12.9 (2)	C4—N2—C7—C8	175.7 (2)
O2—S1—C1—C2	143.19 (18)	N3—N2—C7—C11	176.7 (2)
N1—S1—C1—C2	−102.9 (2)	C4—N2—C7—C11	−7.2 (3)
O1—S1—C1—C6	−167.96 (17)	C12—C11—C7—N2	126.0 (3)
O2—S1—C1—C6	−37.6 (2)	C16—C11—C7—N2	−53.5 (4)
N1—S1—C1—C6	76.33 (19)	C12—C11—C7—C8	−57.6 (4)
C2—C1—C6—C5	−0.3 (3)	C16—C11—C7—C8	122.9 (3)
S1—C1—C6—C5	−179.52 (16)	C12—C11—C16—C15	−0.5 (5)
C2—C3—C4—C5	−1.3 (3)	C7—C11—C16—C15	179.0 (3)
C2—C3—C4—N2	178.9 (2)	N2—C7—C8—C9	0.1 (3)
C7—N2—C4—C3	−48.5 (3)	C11—C7—C8—C9	−176.8 (2)
N3—N2—C4—C3	127.4 (2)	N3—C9—C8—C7	0.4 (3)
C7—N2—C4—C5	131.7 (2)	C10—C9—C8—C7	−179.3 (2)
N3—N2—C4—C5	−52.5 (3)	C16—C11—C12—C13	0.8 (5)
C6—C1—C2—C3	−0.7 (3)	C7—C11—C12—C13	−178.7 (3)
S1—C1—C2—C3	178.52 (18)	C13—C14—C15—C16	0.9 (6)
C4—C3—C2—C1	1.5 (4)	Cl1—C14—C15—C16	−178.5 (3)
C1—C6—C5—C4	0.5 (3)	C11—C16—C15—C14	−0.3 (5)
C3—C4—C5—C6	0.3 (3)	C15—C14—C13—C12	−0.5 (6)
N2—C4—C5—C6	−179.87 (19)	Cl1—C14—C13—C12	178.9 (3)
N2—N3—C9—C8	−0.6 (2)	C11—C12—C13—C14	−0.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···N3ⁱ	0.82 (2)	2.20 (2)	3.010 (3)	169 (2)
N1—H1N1···N3ⁱⁱ	0.84 (3)	2.33 (3)	3.157 (3)	167 (3)
C5—H5···O2ⁱⁱⁱ	0.93	2.48	3.169	131
C3—H3···Cl1^iv	0.93	2.93	3.602	130

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+2, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClN₃O₂S
M_r	347.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.878 (5), 8.209 (5), 12.953 (5)
β (°)	91.016 (5)
V (Å³)	1688.1 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.33 × 0.32 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Analytical (SADABS; Bruker, 2009)
T_min, T_max	0.890, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	17257, 3462, 2594
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.115, 1.03
No. of reflections	3462
No. of parameters	217
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.33

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···N3ⁱ	0.82 (2)	2.20 (2)	3.010 (3)	169 (2)
N1—H1N1···N3ⁱⁱ	0.84 (3)	2.33 (3)	3.157 (3)	167 (3)
C5—H5···O2ⁱⁱⁱ	0.9300	2.4800	3.169	131.00
C3—H3···Cl1^iv	0.9300	2.93	3.602	130.00

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+2, −y+1, −z.

Acknowledgements

GC University is gratefully acknowledged for use of the X-ray diffraction facility. The authors are also thankful to Manchester Metropolitan University and Alazhar University for supporting this study.

References

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