3-{[5-(4-Chloro­phen­yl)-3-methyl-1H-pyrazol-1-yl]meth­yl}-4-m-tolyl-1H-1,2,4-triazole-5(4H)-thione

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

doi:10.1107/S1600536813013494

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Pages o936-o937

doi:10.1107/S1600536813013494

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3-{[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]methyl}-4-m-tolyl-1H-1,2,4-triazole-5(4H)-thione

Muhammad A. Farrukh,^a Maqsood Ahmed,^a ^* Shaaban K. Mohamed,^b,^c 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 10 February 2013; accepted 16 May 2013; online 22 May 2013)

In the title compound, C₂₀H₁₈ClN₅S, the toluene and triazole rings are oriented almost perpendicular to each other, making a dihedral angle of 89.97 (9)°, whereas the dihedral angle between cholorophenyl and pyrazole rings is 54.57 (11)°. In the crystal, pairs of N—H⋯N hydrogen bonds link the molecules into inversion dimers. Weaker C—H⋯S and C—H⋯Cl interactions are also present.

Related literature

For medicinal applications of 1, 2, 4-triazoles, see: Lipinski (1983 ); Ram & Vlietinck (1988 ); Akahoshi et al. (1998 ); Young et al. (2001 ); Ouyang et al. (2005 ); Dolzhenko et al. (2007 ). For general background to the coordination chemistry of triazoles, see: Mishra et al. (1989 ); Klingele & Brooker (2003 ); Beckmann & Brooker (2003 ); Ferrer et al. (2004 ); Castineiras & Garcia-Santos (2008 ).

Experimental

Crystal data

C₂₀H₁₈ClN₅S
M_r = 395.90
Monoclinic, P 2₁ /n
a = 8.328 (5) Å
b = 16.407 (5) Å
c = 14.759 (5) Å
β = 99.509 (5)°
V = 1988.9 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 296 K
0.61 × 0.53 × 0.52 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: analytical {SADABS; Bruker, 2009 ) T_min = 0.833, T_max = 0.855
38237 measured reflections
3914 independent reflections
3207 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.112
S = 1.04
3914 reflections
250 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—HN4⋯N1ⁱ	0.88 (2)	2.02 (2)	2.888 (2)	166 (2)
C6—H6⋯S1ⁱⁱ	0.93	3.00	3.790 (3)	144
C20—H14⋯Cl1ⁱⁱⁱ	0.93	2.98	3.537 (4)	120
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+1.

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 for Windows (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. DOI: 10.1107/S1600536813013494/gw2132sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813013494/gw2132Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813013494/gw2132Isup3.cml

checkCIF report

Comment top

1, 2, 4-Triazole compounds are used as reagents and ligands for the synthesis of biologically active compounds (Lipinski, 1983; Ram & Vlietinck, 1988; Akahoshi et al., 1998; Young et al., 2001; Ouyang et al., 2005; Dolzhenko et al., 2007) and metal complexes (Klingele & Brooker 2003; Beckmann & Brooker 2003; Mishra et al., 1989; Ferrer et al., 2004; Castineiras & Garcia-Santos, 2008). Further to our study on synthesis of bioactive heterocyclic compounds we herein report the synthesis and crystal structure of the title compound.

There is one molecule in the asymmetric unit and four molecules in the unit cell. 1, 2, 4 Triazole ring is oriented almost perpendicular to the toluene ring and the torsion angle between the two rings is 92.6 (2) ° as calculated on the basis of C13—N3—C14—C20 atoms. The diazole ring and the adjacent cholorobenzene ring adopt a twisted geometry and the torsion angle between them is -127.2 (2) ° as calculated using C3—C4—C7—N2 atoms. The molecular assembly is mainly built upon a reciprocal pair of intermolecular N4—H4···N1 type hydrogen bonds between two adjacent molecules which result in the formation of a molecular dimer. The D—H···A distance in each case is 2.02 Å. There are also some C—H···π interactions, a C—H···S interaction and a C—H···Cl interaction which help to stabilize the molecular assembly. The S1 atom accepts the H6 atom from C6 to form a C—H···S type weaker hydrogen bond at a distance of 2.998 Å with a D—H···A angle of 143.87°. Similarly the Cl1 atom accepts the H14 atom from C20 to form a C—H···Cl type weaker hydrogen bond at a distance of 2.978 Å with a D—H···A angle of 120.0°.

Related literature top

For medicinal applications of 1, 2, 4-triazoles, see: Lipinski (1983); Ram & Vlietinck (1988); Akahoshi et al. (1998); Young et al. (2001); Ouyang et al. (2005); Dolzhenko et al. (2007). For general background to the coordination chemistry of triazoles, see: Mishra et al. (1989); Klingele & Brooker (2003); Beckmann & Brooker (2003); Ferrer et al. (2004); Castineiras & Garcia-Santos (2008).

Experimental top

A solution of 2 N sodium hydroxide solution (2 ml) was added in dropwise to a solution of 5 mmol (2.07 g) 2-{[5-(4-chlorophenyl)-3-methyl-1H-pyrazol-1-yl]acetyl}-N-(3-methylphenyl)hydrazinecarbothioamide in 50 ml e thanol. The reaction mixture was then refluxed for 7 h, cooled and filtered. The filtrate was acidified with 2 N hydrochloric acid. The separated solid was collected, washed, and crystallized from ethanol in an excellent yield (92%). Single crystals suitable for X-ray diffraction were obtained from slow evaporation solution of the title compound in ethanol at room temperature (M.p. 433–435 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 for Windows (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 atom numbering scheme and thermal ellipsoids drawn at 30% probability level.
	Fig. 2. A view of the molecular packing along b axis.
	Fig. 3. A dimer of molecules formed by the intermolecular N—H···N type hydrogen bonds. The H atoms not involved in any interaction have been omitted for the reason of clarity. [Symmetry code: (i) 2-x, 1-y, 1-z.]
	Fig. 4. A view of the molecular packing showing weak intermolecular C—H···π and C—H···S interactions. [Symmetry codes: (i) 1-x, -y, 1-z; (ii) 1/2;+x, 1/2-y, 1/2+z.]

3-{[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]methyl}-4-m-tolyl-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₂₀H₁₈ClN₅S	F(000) = 824
M_r = 395.90	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 143 reflections
a = 8.328 (5) Å	θ = 1.9–26.5°
b = 16.407 (5) Å	µ = 0.31 mm⁻¹
c = 14.759 (5) Å	T = 296 K
β = 99.509 (5)°	Block, colourless
V = 1988.9 (15) Å³	0.61 × 0.53 × 0.52 mm
Z = 4

Data collection top

Bruker APEXII CCD detector diffractometer	3914 independent reflections
Radiation source: fine-focus sealed tube	3207 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: analytical {SADABS; Bruker, 2009)	h = −10→10
T_min = 0.833, T_max = 0.855	k = −20→20
38237 measured reflections	l = −18→18

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0474P)² + 0.8662P] where P = (F_o² + 2F_c²)/3
3914 reflections	(Δ/σ)_max = 0.008
250 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₀H₁₈ClN₅S	V = 1988.9 (15) Å³
M_r = 395.90	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.328 (5) Å	µ = 0.31 mm⁻¹
b = 16.407 (5) Å	T = 296 K
c = 14.759 (5) Å	0.61 × 0.53 × 0.52 mm
β = 99.509 (5)°

Data collection top

Bruker APEXII CCD detector diffractometer	3914 independent reflections
Absorption correction: analytical {SADABS; Bruker, 2009)	3207 reflections with I > 2σ(I)
T_min = 0.833, T_max = 0.855	R_int = 0.031
38237 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.23 e Å⁻³
3914 reflections	Δρ_min = −0.26 e Å⁻³
250 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	0.89331 (8)	0.45028 (4)	0.23277 (4)	0.0738 (2)
Cl1	0.87201 (11)	−0.10903 (4)	0.56431 (6)	0.1018 (3)
N2	0.83576 (17)	0.30784 (8)	0.58288 (10)	0.0420 (3)
N3	0.91296 (16)	0.36199 (8)	0.39136 (10)	0.0402 (3)
N1	0.76919 (18)	0.38104 (9)	0.59822 (10)	0.0460 (3)
N4	1.08074 (19)	0.46017 (9)	0.40066 (11)	0.0474 (4)
N5	1.10761 (18)	0.42403 (9)	0.48545 (11)	0.0468 (4)
C12	1.00462 (19)	0.36448 (10)	0.47753 (11)	0.0396 (4)
C14	0.78212 (19)	0.30653 (10)	0.35998 (11)	0.0388 (4)
C15	0.6269 (2)	0.32639 (10)	0.37306 (12)	0.0438 (4)
H19	0.6080	0.3758	0.4003	0.053*
C4	0.7762 (2)	0.15886 (10)	0.58340 (12)	0.0453 (4)
C13	0.9620 (2)	0.42534 (10)	0.34117 (13)	0.0457 (4)
C11	0.9930 (2)	0.30522 (11)	0.55227 (12)	0.0457 (4)
H11A	1.0112	0.2507	0.5307	0.055*
H11B	1.0780	0.3168	0.6040	0.055*
C20	0.8140 (2)	0.23434 (11)	0.31944 (13)	0.0492 (4)
H14	0.9187	0.2219	0.3097	0.059*
C9	0.6232 (2)	0.36378 (11)	0.61886 (13)	0.0506 (4)
C16	0.4988 (2)	0.27320 (12)	0.34583 (13)	0.0491 (4)
C18	0.5317 (2)	0.20020 (12)	0.30670 (13)	0.0548 (5)
H16	0.4474	0.1634	0.2889	0.066*
C7	0.7349 (2)	0.24523 (10)	0.59382 (12)	0.0445 (4)
C6	0.9473 (3)	0.04243 (13)	0.62598 (15)	0.0643 (6)
H6	1.0406	0.0195	0.6597	0.077*
C8	0.5974 (2)	0.27957 (11)	0.61661 (14)	0.0529 (5)
H8	0.5050	0.2523	0.6283	0.063*
C5	0.9165 (3)	0.12459 (12)	0.63229 (13)	0.0564 (5)
H5	0.9907	0.1574	0.6698	0.068*
C19	0.6871 (3)	0.18060 (12)	0.29343 (14)	0.0574 (5)
H15	0.7066	0.1310	0.2668	0.069*
C3	0.6710 (2)	0.10971 (11)	0.52508 (14)	0.0551 (5)
H3	0.5775	0.1321	0.4910	0.066*
C2	0.7034 (3)	0.02772 (12)	0.51691 (16)	0.0640 (6)
H2	0.6342	−0.0049	0.4763	0.077*
C1	0.8389 (3)	−0.00466 (12)	0.56953 (16)	0.0605 (5)
C17	0.3290 (3)	0.29548 (17)	0.3590 (2)	0.0794 (7)
H17A	0.2554	0.2525	0.3357	0.119*
H17B	0.2966	0.3450	0.3264	0.119*
H17C	0.3266	0.3032	0.4232	0.119*
C10	0.5133 (3)	0.43051 (14)	0.64055 (19)	0.0749 (7)
H10A	0.5713	0.4813	0.6453	0.112*
H10B	0.4776	0.4189	0.6978	0.112*
H10C	0.4206	0.4341	0.5925	0.112*
HN4	1.130 (2)	0.5065 (14)	0.3917 (14)	0.056 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0868 (4)	0.0712 (4)	0.0609 (3)	−0.0027 (3)	0.0045 (3)	0.0243 (3)
Cl1	0.1391 (7)	0.0416 (3)	0.1352 (7)	0.0167 (3)	0.0533 (5)	0.0124 (3)
N2	0.0469 (8)	0.0364 (7)	0.0430 (8)	−0.0039 (6)	0.0086 (6)	−0.0001 (6)
N3	0.0405 (7)	0.0361 (7)	0.0437 (7)	−0.0015 (6)	0.0060 (6)	0.0015 (6)
N1	0.0528 (9)	0.0380 (7)	0.0480 (8)	−0.0046 (6)	0.0106 (7)	−0.0024 (6)
N4	0.0500 (8)	0.0369 (8)	0.0580 (9)	−0.0073 (7)	0.0169 (7)	−0.0003 (7)
N5	0.0456 (8)	0.0439 (8)	0.0518 (9)	−0.0070 (6)	0.0110 (7)	−0.0043 (7)
C12	0.0371 (8)	0.0379 (8)	0.0443 (9)	0.0000 (7)	0.0081 (7)	−0.0030 (7)
C14	0.0411 (8)	0.0350 (8)	0.0391 (8)	−0.0011 (6)	0.0033 (6)	0.0012 (6)
C15	0.0457 (9)	0.0398 (9)	0.0463 (9)	0.0016 (7)	0.0083 (7)	−0.0041 (7)
C4	0.0549 (10)	0.0377 (9)	0.0444 (9)	−0.0048 (8)	0.0117 (8)	0.0039 (7)
C13	0.0480 (9)	0.0367 (8)	0.0545 (10)	0.0030 (7)	0.0147 (8)	0.0030 (7)
C11	0.0425 (9)	0.0477 (10)	0.0461 (10)	−0.0012 (7)	0.0050 (7)	0.0030 (7)
C20	0.0498 (10)	0.0450 (10)	0.0523 (10)	0.0062 (8)	0.0071 (8)	−0.0048 (8)
C9	0.0540 (10)	0.0464 (10)	0.0536 (11)	−0.0045 (8)	0.0151 (8)	−0.0054 (8)
C16	0.0445 (9)	0.0555 (11)	0.0470 (10)	−0.0047 (8)	0.0067 (8)	0.0019 (8)
C18	0.0605 (11)	0.0508 (11)	0.0496 (10)	−0.0170 (9)	−0.0005 (9)	−0.0017 (8)
C7	0.0523 (10)	0.0402 (9)	0.0409 (9)	−0.0078 (8)	0.0078 (7)	0.0016 (7)
C6	0.0717 (13)	0.0574 (12)	0.0630 (13)	0.0118 (11)	0.0093 (11)	0.0171 (10)
C8	0.0533 (10)	0.0478 (10)	0.0609 (11)	−0.0107 (8)	0.0192 (9)	−0.0012 (9)
C5	0.0649 (12)	0.0531 (11)	0.0485 (10)	−0.0038 (9)	0.0014 (9)	0.0046 (9)
C19	0.0731 (13)	0.0392 (9)	0.0575 (11)	−0.0003 (9)	0.0036 (10)	−0.0106 (8)
C3	0.0544 (11)	0.0431 (10)	0.0653 (12)	−0.0049 (8)	0.0026 (9)	0.0015 (9)
C2	0.0693 (13)	0.0439 (11)	0.0789 (15)	−0.0115 (10)	0.0124 (11)	−0.0084 (10)
C1	0.0747 (14)	0.0390 (10)	0.0729 (14)	0.0043 (9)	0.0268 (11)	0.0095 (9)
C17	0.0482 (12)	0.0956 (18)	0.0968 (18)	−0.0064 (12)	0.0191 (12)	−0.0075 (15)
C10	0.0723 (14)	0.0598 (13)	0.0986 (19)	0.0036 (11)	0.0323 (13)	−0.0114 (12)

Geometric parameters (Å, º) top

S1—C13	1.659 (2)	C20—H14	0.9300
Cl1—C1	1.738 (2)	C9—C8	1.398 (3)
N2—C7	1.353 (2)	C9—C10	1.495 (3)
N2—N1	1.357 (2)	C16—C18	1.377 (3)
N2—C11	1.455 (2)	C16—C17	1.504 (3)
N3—C12	1.372 (2)	C18—C19	1.379 (3)
N3—C13	1.377 (2)	C18—H16	0.9300
N3—C14	1.436 (2)	C7—C8	1.367 (3)
N1—C9	1.332 (2)	C6—C1	1.363 (3)
N4—C13	1.337 (2)	C6—C5	1.378 (3)
N4—N5	1.369 (2)	C6—H6	0.9300
N4—HN4	0.89 (2)	C8—H8	0.9300
N5—C12	1.293 (2)	C5—H5	0.9300
C12—C11	1.486 (2)	C19—H15	0.9300
C14—C20	1.373 (2)	C3—C2	1.381 (3)
C14—C15	1.377 (2)	C3—H3	0.9300
C15—C16	1.385 (2)	C2—C1	1.367 (3)
C15—H19	0.9300	C2—H2	0.9300
C4—C3	1.382 (3)	C17—H17A	0.9600
C4—C5	1.387 (3)	C17—H17B	0.9600
C4—C7	1.472 (2)	C17—H17C	0.9600
C11—H11A	0.9700	C10—H10A	0.9600
C11—H11B	0.9700	C10—H10B	0.9600
C20—C19	1.381 (3)	C10—H10C	0.9600

C7—N2—N1	111.89 (14)	C15—C16—C17	120.32 (19)
C7—N2—C11	128.53 (15)	C16—C18—C19	121.26 (17)
N1—N2—C11	119.43 (13)	C16—C18—H16	119.4
C12—N3—C13	107.90 (14)	C19—C18—H16	119.4
C12—N3—C14	126.46 (14)	N2—C7—C8	106.16 (16)
C13—N3—C14	125.54 (14)	N2—C7—C4	123.88 (16)
C9—N1—N2	105.27 (14)	C8—C7—C4	129.96 (16)
C13—N4—N5	113.98 (15)	C1—C6—C5	118.9 (2)
C13—N4—HN4	125.5 (13)	C1—C6—H6	120.5
N5—N4—HN4	119.9 (13)	C5—C6—H6	120.5
C12—N5—N4	103.82 (14)	C7—C8—C9	106.34 (16)
N5—C12—N3	111.46 (15)	C7—C8—H8	126.8
N5—C12—C11	123.46 (16)	C9—C8—H8	126.8
N3—C12—C11	125.05 (15)	C6—C5—C4	120.8 (2)
C20—C14—C15	121.24 (16)	C6—C5—H5	119.6
C20—C14—N3	119.76 (15)	C4—C5—H5	119.6
C15—C14—N3	118.99 (15)	C18—C19—C20	120.32 (18)
C14—C15—C16	120.39 (16)	C18—C19—H15	119.8
C14—C15—H19	119.8	C20—C19—H15	119.8
C16—C15—H19	119.8	C4—C3—C2	120.66 (19)
C3—C4—C5	118.72 (18)	C4—C3—H3	119.7
C3—C4—C7	119.44 (17)	C2—C3—H3	119.7
C5—C4—C7	121.82 (17)	C1—C2—C3	118.9 (2)
N4—C13—N3	102.84 (15)	C1—C2—H2	120.5
N4—C13—S1	128.86 (14)	C3—C2—H2	120.5
N3—C13—S1	128.28 (14)	C6—C1—C2	121.89 (19)
N2—C11—C12	112.56 (14)	C6—C1—Cl1	119.44 (18)
N2—C11—H11A	109.1	C2—C1—Cl1	118.67 (18)
C12—C11—H11A	109.1	C16—C17—H17A	109.5
N2—C11—H11B	109.1	C16—C17—H17B	109.5
C12—C11—H11B	109.1	H17A—C17—H17B	109.5
H11A—C11—H11B	107.8	C16—C17—H17C	109.5
C14—C20—C19	118.55 (17)	H17A—C17—H17C	109.5
C14—C20—H14	120.7	H17B—C17—H17C	109.5
C19—C20—H14	120.7	C9—C10—H10A	109.5
N1—C9—C8	110.33 (17)	C9—C10—H10B	109.5
N1—C9—C10	120.48 (18)	H10A—C10—H10B	109.5
C8—C9—C10	129.19 (19)	C9—C10—H10C	109.5
C18—C16—C15	118.22 (17)	H10A—C10—H10C	109.5
C18—C16—C17	121.46 (18)	H10B—C10—H10C	109.5

C7—N2—N1—C9	−0.24 (19)	C14—C15—C16—C18	0.8 (3)
C11—N2—N1—C9	175.82 (15)	C14—C15—C16—C17	−179.16 (19)
C13—N4—N5—C12	1.10 (19)	C15—C16—C18—C19	−1.0 (3)
N4—N5—C12—N3	−0.47 (18)	C17—C16—C18—C19	178.9 (2)
N4—N5—C12—C11	177.59 (15)	N1—N2—C7—C8	0.4 (2)
C13—N3—C12—N5	−0.25 (19)	C11—N2—C7—C8	−175.26 (16)
C14—N3—C12—N5	−176.79 (15)	N1—N2—C7—C4	−178.73 (15)
C13—N3—C12—C11	−178.27 (15)	C11—N2—C7—C4	5.7 (3)
C14—N3—C12—C11	5.2 (3)	C3—C4—C7—N2	−127.2 (2)
C12—N3—C14—C20	−91.4 (2)	C5—C4—C7—N2	54.4 (3)
C13—N3—C14—C20	92.6 (2)	C3—C4—C7—C8	54.0 (3)
C12—N3—C14—C15	87.3 (2)	C5—C4—C7—C8	−124.4 (2)
C13—N3—C14—C15	−88.7 (2)	N2—C7—C8—C9	−0.3 (2)
C20—C14—C15—C16	0.4 (3)	C4—C7—C8—C9	178.69 (18)
N3—C14—C15—C16	−178.24 (16)	N1—C9—C8—C7	0.2 (2)
N5—N4—C13—N3	−1.22 (19)	C10—C9—C8—C7	−179.6 (2)
N5—N4—C13—S1	−179.74 (13)	C1—C6—C5—C4	1.1 (3)
C12—N3—C13—N4	0.86 (17)	C3—C4—C5—C6	−2.7 (3)
C14—N3—C13—N4	177.44 (14)	C7—C4—C5—C6	175.69 (18)
C12—N3—C13—S1	179.39 (14)	C16—C18—C19—C20	0.0 (3)
C14—N3—C13—S1	−4.0 (3)	C14—C20—C19—C18	1.1 (3)
C7—N2—C11—C12	129.99 (18)	C5—C4—C3—C2	1.2 (3)
N1—N2—C11—C12	−45.3 (2)	C7—C4—C3—C2	−177.28 (18)
N5—C12—C11—N2	117.51 (18)	C4—C3—C2—C1	1.9 (3)
N3—C12—C11—N2	−64.7 (2)	C5—C6—C1—C2	2.1 (3)
C15—C14—C20—C19	−1.3 (3)	C5—C6—C1—Cl1	−177.48 (16)
N3—C14—C20—C19	177.29 (16)	C3—C2—C1—C6	−3.6 (3)
N2—N1—C9—C8	0.0 (2)	C3—C2—C1—Cl1	175.96 (17)
N2—N1—C9—C10	179.80 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—HN4···N1ⁱ	0.88 (2)	2.02 (2)	2.888 (2)	166 (2)
C5—H5···C16ⁱⁱ	0.93	2.83	3.536 (3)	134
C6—H6···S1ⁱⁱ	0.93	3.00	3.790 (3)	144
C2—H2···C2ⁱⁱⁱ	0.93	2.85	3.464 (4)	124
C20—H14···Cl1^iv	0.93	2.98	3.537 (4)	120

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈ClN₅S
M_r	395.90
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.328 (5), 16.407 (5), 14.759 (5)
β (°)	99.509 (5)
V (Å³)	1988.9 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.61 × 0.53 × 0.52

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	Analytical {SADABS; Bruker, 2009)
T_min, T_max	0.833, 0.855
No. of measured, independent and observed [I > 2σ(I)] reflections	38237, 3914, 3207
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.112, 1.04
No. of reflections	3914
No. of parameters	250
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (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
N4—HN4···N1ⁱ	0.88 (2)	2.02 (2)	2.888 (2)	166 (2)
C6—H6···S1ⁱⁱ	0.93	3.00	3.790 (3)	144
C20—H14···Cl1ⁱⁱⁱ	0.93	2.98	3.537 (4)	120

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

Acknowledgements

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

References

Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, M., Inoue, Y., Fukaya, C., Naito, Y., Imagawa, T. & Nakamura, N. (1998). J. Med. Chem. 41, 2985–2993. Web of Science CrossRef CAS PubMed Google Scholar
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Volume 69| Part 6| June 2013| Pages o936-o937

doi:10.1107/S1600536813013494

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

3-{[5-(4-Chloro­phen­yl)-3-methyl-1H-pyrazol-1-yl]meth­yl}-4-m-tolyl-1H-1,2,4-triazole-5(4H)-thione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-{[5-(4-Chlorophenyl)-3-methyl-1H-pyrazol-1-yl]methyl}-4-m-tolyl-1H-1,2,4-triazole-5(4H)-thione