organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 2| February 2013| Pages o295-o296

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

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[Mukherjee, R. (2000). Coord. Chem. Rev. 203, 151-218.]); Halcrow (2009[Halcrow, M. A. (2009). Dalton Trans. pp. 2059-2073.]). For the synthesis and pharmaceutical applications of pyrazole compounds, see, for example: Ranatunge et al. (2004[Ranatunge, R. R., Earl, R. A., Garvey, D. S., Janero, D. R., Letts, L. G., Martino, A. M., Murty, M. G., Richardson, S. K., Schwalb, D. J., Young, D. V. & Zemtseva, I. S. (2004). Bioorg. Med. Chem. Lett. 14, 6049-6052.]); Szabo et al. (2008[Szabo, G., Fischer, J., Kis-Varga, A. & Gyires, K. (2008). J. Med. Chem. 51, 142-147.]); Bekhit & Abdel-Aziem (2004[Bekhit, A. A. & Abdel-Aziem, T. (2004). Bioorg. Med. Chem. 12, 1935-1945.]); Bekhit et al. (2006[Bekhit, A. A., Abdel-Rahman, H. M. & Guemel, A. A. (2006). Arch. Pharm. Chem. Life Sci. 339, 81-87.]); Rostom et al. (2003[Rostom, S. A. F., Shalaby, M. A. & El-Demellawy, M. A. (2003). Eur. J. Med. Chem. 38, 959-974.]); Gökhan-Kelekçi et al. (2007[Gökhan-Kelekçi, N., Yabanoğlu, S., Küpeli, E., Salgin, U., Özgen, Ö., Uçar, G., Yeşilada, E., Kendi, E., Yeşilada, A. & Bilgin, A. A. (2007). Bioorg. Med. Chem. 15, 5775-5786.]); Lin et al. (2007[Lin, R., Chiu, G., Yu, Y., Connolly, P. J., Li, S., Lu, Y., Adams, M., Fuentes-Pesquera, A. R., Emanuel, S. L. & Greenberger, L. M. (2007). Bioorg. Med. Chem. Lett. 17, 4557-4561.]); El-Moghazy et al. (2012[El-Moghazy, S. M., Barsoum, F. F., Abdel-Rahman, H. M. & Marzouk, A. A. (2012). Med. Chem. Res. 21, 1722-1733.]); Sakya et al. (2008[Sakya, S. M., Shavnya, A., Cheng, H., Rast, C. L. B., Li, J., Koss, D. A., Jaynes, B. H., Mann, D. W., Petras, C. F., Seibel, S. B., Haven, M. L. & Lynch, M. P. (2008). Bioorg. Med. Chem. Lett. 18, 1042-1045.]); Shen et al. (2004[Shen, D. M., Shu, M., Mills, S. G., Chapman, K. T., Malkowitz, L., Springer, M. S., Gould, S. L., DeMartino, J. A., Siciliano, S. J., Kwei, G. Y., Carella, A., Carver, G., Holmes, K., Schleif, W. A., Danzeisen, R., Hazuda, D., Kessler, J., Lineberger, J., Miller, M. D. & Emini, E. A. (2004). Bioorg. Med. Chem. Lett. 14, 935-939.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14ClN3O2S

  • Mr = 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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.890, Tmax = 0.938

  • 17257 measured reflections

  • 3462 independent reflections

  • 2594 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.34 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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) [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[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


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).

Refinement top

The H atoms attached to N1 were located in a difference map and were refined freely. All the H atoms attached to aromatic carbon atoms were initially located in the difference map but subsequently refined with a distance restraint of 0.93 Å and Uiso(H) = 1.2Ueq(C). The H atoms attached to C10 atom were positioned geometrically at idealized positions for methyl and were refined with C—H distance of 0.96 Å and Uiso(H) = 1.5Ueq(C).

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
[Figure 1] Fig. 1. An ORTEPIII diagram of the molecule showing the atom numbering scheme and thermal ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the molecular packing along the a axis.
[Figure 3] 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
[Figure 4] 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
C16H14ClN3O2SF(000) = 720
Mr = 347.81Dx = 1.369 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 133 reflections
a = 15.878 (5) Åθ = 2.7–26.0°
b = 8.209 (5) ŵ = 0.36 mm1
c = 12.953 (5) ÅT = 296 K
β = 91.016 (5)°Block, colourless
V = 1688.1 (13) Å30.33 × 0.32 × 0.18 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3462 independent reflections
Radiation source: fine-focus sealed tube2594 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω and ϕ scansθmax = 26.4°, θmin = 2.8°
Absorption correction: analytical
(SADABS; Bruker, 2009)
h = 1919
Tmin = 0.890, Tmax = 0.938k = 1010
17257 measured reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H 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 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.33 e Å3
Crystal data top
C16H14ClN3O2SV = 1688.1 (13) Å3
Mr = 347.81Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.878 (5) ŵ = 0.36 mm1
b = 8.209 (5) ÅT = 296 K
c = 12.953 (5) Å0.33 × 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)
Tmin = 0.890, Tmax = 0.938Rint = 0.030
17257 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.115H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.34 e Å3
3462 reflectionsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
S10.62888 (4)0.52544 (6)0.26035 (4)0.03590 (16)
Cl11.07396 (5)0.23198 (14)0.03417 (10)0.1065 (4)
O10.70283 (10)0.5918 (2)0.30442 (11)0.0545 (5)
N10.55446 (14)0.6528 (2)0.27978 (14)0.0381 (4)
N30.62419 (11)0.5109 (2)0.25734 (12)0.0338 (4)
O20.59721 (12)0.37105 (18)0.29389 (11)0.0551 (5)
N20.68811 (10)0.4740 (2)0.19252 (12)0.0327 (4)
C10.64780 (13)0.5101 (2)0.12544 (14)0.0316 (4)
C30.72856 (14)0.5768 (3)0.02534 (16)0.0434 (5)
H30.77380.63060.05670.052*
C60.59263 (14)0.4216 (3)0.06641 (15)0.0383 (5)
H60.54650.37030.09750.046*
C40.67440 (13)0.4873 (2)0.08368 (14)0.0311 (4)
C110.83783 (14)0.3838 (3)0.19450 (17)0.0467 (6)
C20.71592 (14)0.5872 (3)0.08065 (16)0.0429 (5)
H20.75320.64570.12100.051*
C50.60608 (13)0.4095 (3)0.03862 (15)0.0372 (5)
H50.56940.34930.07880.045*
C90.65766 (15)0.4978 (3)0.35195 (16)0.0403 (5)
C100.60555 (18)0.5323 (3)0.44406 (17)0.0550 (7)
H10A0.55070.56870.42190.082*
H10B0.63220.61560.48510.082*
H10C0.60020.43490.48440.082*
C70.76017 (14)0.4366 (3)0.24501 (16)0.0415 (5)
C160.83766 (17)0.2553 (4)0.1266 (3)0.0688 (8)
H160.78770.19940.11300.083*
C80.74152 (15)0.4516 (3)0.34751 (17)0.0506 (6)
H80.77810.43410.40330.061*
C140.98314 (17)0.2900 (4)0.0978 (3)0.0676 (8)
C120.91258 (18)0.4628 (4)0.2135 (3)0.0808 (10)
H120.91430.54920.25990.097*
C150.91033 (19)0.2080 (4)0.0784 (3)0.0800 (10)
H150.90950.12040.03290.096*
C130.98526 (19)0.4160 (5)0.1648 (3)0.0943 (12)
H131.03550.47100.17810.113*
H2N10.5670 (16)0.747 (3)0.266 (2)0.050 (8)*
H1N10.5061 (18)0.620 (4)0.265 (2)0.061 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0498 (3)0.0367 (3)0.0213 (2)0.0057 (2)0.0010 (2)0.0004 (2)
Cl10.0537 (5)0.1252 (8)0.1417 (9)0.0173 (5)0.0359 (5)0.0154 (7)
O10.0500 (10)0.0833 (12)0.0304 (8)0.0055 (9)0.0090 (7)0.0095 (8)
N10.0445 (12)0.0344 (10)0.0352 (10)0.0008 (9)0.0052 (8)0.0011 (8)
N30.0408 (10)0.0353 (9)0.0254 (8)0.0006 (7)0.0019 (7)0.0009 (7)
O20.0967 (14)0.0358 (8)0.0324 (8)0.0054 (9)0.0079 (8)0.0078 (7)
N20.0359 (9)0.0379 (9)0.0241 (8)0.0004 (7)0.0012 (7)0.0010 (7)
C10.0395 (11)0.0323 (10)0.0229 (9)0.0057 (9)0.0007 (8)0.0003 (8)
C30.0409 (12)0.0568 (14)0.0322 (11)0.0150 (10)0.0038 (9)0.0033 (10)
C60.0434 (12)0.0406 (11)0.0305 (10)0.0086 (10)0.0058 (9)0.0012 (9)
C40.0369 (11)0.0330 (10)0.0235 (9)0.0028 (8)0.0006 (8)0.0011 (8)
C110.0370 (12)0.0625 (15)0.0405 (12)0.0009 (11)0.0062 (10)0.0068 (11)
C20.0423 (12)0.0556 (14)0.0309 (11)0.0108 (11)0.0035 (9)0.0075 (10)
C50.0419 (12)0.0399 (11)0.0297 (10)0.0081 (9)0.0004 (9)0.0046 (9)
C90.0529 (14)0.0426 (12)0.0255 (10)0.0081 (10)0.0005 (9)0.0010 (9)
C100.0704 (17)0.0659 (16)0.0290 (11)0.0104 (13)0.0082 (11)0.0044 (11)
C70.0388 (12)0.0524 (13)0.0331 (11)0.0018 (10)0.0069 (9)0.0033 (10)
C160.0398 (14)0.078 (2)0.089 (2)0.0038 (13)0.0061 (14)0.0206 (17)
C80.0510 (14)0.0721 (17)0.0284 (11)0.0033 (12)0.0110 (10)0.0048 (11)
C140.0388 (14)0.083 (2)0.081 (2)0.0101 (14)0.0075 (14)0.0159 (17)
C120.0460 (16)0.102 (2)0.095 (2)0.0116 (16)0.0052 (16)0.027 (2)
C150.0517 (18)0.088 (2)0.100 (3)0.0071 (16)0.0087 (17)0.0284 (19)
C130.0375 (16)0.111 (3)0.134 (3)0.0149 (17)0.0036 (18)0.018 (3)
Geometric parameters (Å, º) top
S1—O11.4229 (17)C11—C161.373 (4)
S1—O21.4284 (18)C11—C71.471 (3)
S1—N11.594 (2)C2—H20.9300
S1—C11.772 (2)C5—H50.9300
Cl1—C141.740 (3)C9—C81.387 (3)
N1—H2N10.82 (3)C9—C101.491 (3)
N1—H1N10.84 (3)C10—H10A0.9600
N3—C91.331 (3)C10—H10B0.9600
N3—N21.363 (2)C10—H10C0.9600
N2—C71.356 (3)C7—C81.371 (3)
N2—C41.427 (2)C16—C151.378 (4)
C1—C21.373 (3)C16—H160.9300
C1—C61.380 (3)C8—H80.9300
C3—C41.369 (3)C14—C131.351 (5)
C3—C21.387 (3)C14—C151.357 (4)
C3—H30.9300C12—C131.379 (4)
C6—C51.377 (3)C12—H120.9300
C6—H60.9300C15—H150.9300
C4—C51.380 (3)C13—H130.9300
C11—C121.371 (4)
O1—S1—O2120.40 (11)C6—C5—H5120.3
O1—S1—N1107.47 (12)C4—C5—H5120.3
O2—S1—N1106.13 (12)N3—C9—C8110.59 (19)
O1—S1—C1107.23 (10)N3—C9—C10120.2 (2)
O2—S1—C1106.82 (9)C8—C9—C10129.2 (2)
N1—S1—C1108.33 (10)C9—C10—H10A109.5
S1—N1—H2N1114.2 (18)C9—C10—H10B109.5
S1—N1—H1N1116 (2)H10A—C10—H10B109.5
H2N1—N1—H1N1118 (3)C9—C10—H10C109.5
C9—N3—N2105.06 (17)H10A—C10—H10C109.5
C7—N2—N3111.87 (16)H10B—C10—H10C109.5
C7—N2—C4128.71 (18)N2—C7—C8105.7 (2)
N3—N2—C4119.31 (16)N2—C7—C11123.38 (19)
C2—C1—C6120.78 (18)C8—C7—C11130.8 (2)
C2—C1—S1120.16 (16)C11—C16—C15121.0 (3)
C6—C1—S1119.06 (15)C11—C16—H16119.5
C4—C3—C2119.88 (19)C15—C16—H16119.5
C4—C3—H3120.1C7—C8—C9106.77 (19)
C2—C3—H3120.1C7—C8—H8126.6
C5—C6—C1119.78 (19)C9—C8—H8126.6
C5—C6—H6120.1C13—C14—C15120.7 (3)
C1—C6—H6120.1C13—C14—Cl1120.2 (2)
C3—C4—C5120.80 (18)C15—C14—Cl1119.2 (3)
C3—C4—N2120.02 (18)C11—C12—C13121.0 (3)
C5—C4—N2119.18 (18)C11—C12—H12119.5
C12—C11—C16118.0 (3)C13—C12—H12119.5
C12—C11—C7120.7 (2)C14—C15—C16119.6 (3)
C16—C11—C7121.3 (2)C14—C15—H15120.2
C1—C2—C3119.3 (2)C16—C15—H15120.2
C1—C2—H2120.4C14—C13—C12119.7 (3)
C3—C2—H2120.4C14—C13—H13120.2
C6—C5—C4119.44 (19)C12—C13—H13120.2
C9—N3—N2—C70.7 (2)N2—N3—C9—C10179.11 (19)
C9—N3—N2—C4175.84 (17)N3—N2—C7—C80.5 (2)
O1—S1—C1—C212.9 (2)C4—N2—C7—C8175.7 (2)
O2—S1—C1—C2143.19 (18)N3—N2—C7—C11176.7 (2)
N1—S1—C1—C2102.9 (2)C4—N2—C7—C117.2 (3)
O1—S1—C1—C6167.96 (17)C12—C11—C7—N2126.0 (3)
O2—S1—C1—C637.6 (2)C16—C11—C7—N253.5 (4)
N1—S1—C1—C676.33 (19)C12—C11—C7—C857.6 (4)
C2—C1—C6—C50.3 (3)C16—C11—C7—C8122.9 (3)
S1—C1—C6—C5179.52 (16)C12—C11—C16—C150.5 (5)
C2—C3—C4—C51.3 (3)C7—C11—C16—C15179.0 (3)
C2—C3—C4—N2178.9 (2)N2—C7—C8—C90.1 (3)
C7—N2—C4—C348.5 (3)C11—C7—C8—C9176.8 (2)
N3—N2—C4—C3127.4 (2)N3—C9—C8—C70.4 (3)
C7—N2—C4—C5131.7 (2)C10—C9—C8—C7179.3 (2)
N3—N2—C4—C552.5 (3)C16—C11—C12—C130.8 (5)
C6—C1—C2—C30.7 (3)C7—C11—C12—C13178.7 (3)
S1—C1—C2—C3178.52 (18)C13—C14—C15—C160.9 (6)
C4—C3—C2—C11.5 (4)Cl1—C14—C15—C16178.5 (3)
C1—C6—C5—C40.5 (3)C11—C16—C15—C140.3 (5)
C3—C4—C5—C60.3 (3)C15—C14—C13—C120.5 (6)
N2—C4—C5—C6179.87 (19)Cl1—C14—C13—C12178.9 (3)
N2—N3—C9—C80.6 (2)C11—C12—C13—C140.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H2N1···N3i0.82 (2)2.20 (2)3.010 (3)169 (2)
N1—H1N1···N3ii0.84 (3)2.33 (3)3.157 (3)167 (3)
C5—H5···O2iii0.932.483.169131
C3—H3···Cl1iv0.932.933.602130
Symmetry codes: (i) x, y+3/2, z1/2; (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 formulaC16H14ClN3O2S
Mr347.81
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)15.878 (5), 8.209 (5), 12.953 (5)
β (°) 91.016 (5)
V3)1688.1 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.36
Crystal size (mm)0.33 × 0.32 × 0.18
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionAnalytical
(SADABS; Bruker, 2009)
Tmin, Tmax0.890, 0.938
No. of measured, independent and
observed [I > 2σ(I)] reflections
17257, 3462, 2594
Rint0.030
(sin θ/λ)max1)0.626
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.115, 1.03
No. of reflections3462
No. of parameters217
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N1—H2N1···N3i0.82 (2)2.20 (2)3.010 (3)169 (2)
N1—H1N1···N3ii0.84 (3)2.33 (3)3.157 (3)167 (3)
C5—H5···O2iii0.93002.48003.169131.00
C3—H3···Cl1iv0.93002.933.602130.00
Symmetry codes: (i) x, y+3/2, z1/2; (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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Volume 69| Part 2| February 2013| Pages o295-o296
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