4-[5-(4-Chloro-phen-yl)-3-methyl-1H-pyrazol-1-yl]benzene-sulfonamide.

In the title compound, C(16)H(14)ClN(3)O(2)S, the dihedral angle between the benzene and pyrazole rings is 52.75 (2)°, while that between the pyrazole and 4-chloro-phenyl rings is 54.0 (3)°. The terminal sulfonamide group adopts an approximately tetra-hedral 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 = 347.81

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.03

3462 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

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 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global_Publ_Block. DOI: 10.1107/S1600536813002134/sj5296sup1.cif

Click here for additional data file.

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

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813002134/sj5296Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H14ClN3O2S	F(000) = 720
Mr = 347.81	Dx = 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

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

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(Fo2) + (0.0506P)2 + 0.8701P] where P = (Fo2 + 2Fc2)/3
3462 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···Cl1iv	0.93	2.93	3.602	130

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⋯Cl1iv	0.93	2.93	3.602	130

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .