4-(3-Methyl­phen­yl)-3-[(3-methyl-5-phenyl-1H-pyrazol-1-yl)meth­yl]-4,5-di­hydro-1H-1,2,4-triazole-5-thione

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Marzouk, A.A.; Abdel-Rahman, H.M.; Hawaiz, F.E.

doi:10.1107/S2414314617001845

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 2| February 2017| x170184

https://doi.org/10.1107/S2414314617001845

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access

4-(3-Methylphenyl)-3-[(3-methyl-5-phenyl-1H-pyrazol-1-yl)methyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt,^d Adel A. Marzouk,^e Hamdy M. Abdel-Rahman ^f and Farouq E. Hawaiz ^g ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^cChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^ePharmaceutical Chemistry Department, Faculty of Pharmacy, Al Azhar University, 71515 Assiut, Egypt, ^fFaculty of Pharmacy, Medicinal Chemistry Department, Assiut University, Assiut 71526, Egypt, and ^gChemistry Department, College of Education, Salahaddin University-Hawler, Erbil, Kurdistan Region, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 February 2017; accepted 2 February 2017; online 7 February 2017)

The title compound, C₂₀H₁₉N₅S, adopts a `contorted' conformation and the dihedral angle between the heterocyclic rings is 86.54 (6)°. In the crystal, complementary N—H⋯N hydrogen bonds form centrosymmetric dimers, which generate R₂²(14) loops. The dimers stack along the a-axis direction with adjacent stacks having their aromatic rings directed towards one another.

Keywords: crystal structure; hydrogen bond; pyrazole; triazole; dimer.

CCDC reference: 1530646

Structure description

As part of our ongoing studies of triazole derivatives (Mague et al., 2015 ), we herein describe the synthesis and crystal structure of the title compound (Fig. 1). The dihedral angle between the planes of the C4–C8 and N1–N3/C1/C2 rings is 83.83 (5)° while that between the latter plane and that of the N4/N5/C11–C13 ring is 86.54 (6)°. The dihedral angle between the planes of the N4/N5/C11–C13 and C15–C20 rings is 52.92 (5)°. The molecule may be described as adopting a `contorted' conformation.

Figure 1
The title molecule with 25% probability ellipsoids.

In the crystal, complementary N3—H3⋯N5ⁱ hydrogen bonds form centrosymmetric dimers, which generate R₂²(14) loops (Table 1 and Fig. 2). These dimers stack along the a-axis direction with the aromatic rings pointing towards those of adjacent stacks (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯N5ⁱ	0.91	1.99	2.8765 (18)	164
Symmetry code: (i) -x, -y+2, -z+1.

Figure 2
The packing, viewed along the a axis, with N—H⋯N hydrogen bonds shown as dotted lines.

Synthesis and crystallization

A solution of 2-(2-(5-phenyl-3-methyl-1H-pyrazol-1-yl)acetyl)-N-p-tolylhydrazinecarbothioamide (1.53 g; 4 mmol) in ethanol (50 ml) was added dropwise to 2 N sodium hydroxide solution (20 ml). The reaction mixture was then refluxed for 2 h, cooled, filtered and the filtrate was acidified with 2 N hydrochloric acid solution. The separated solid was collected, washed with water and recrystallized from pure EtOH.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₅S
M_r	361.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	8.3386 (5), 15.5969 (9), 14.9334 (8)
β (°)	99.834 (1)
V (Å³)	1913.65 (19)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.18
Crystal size (mm)	0.46 × 0.39 × 0.26

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.87, 0.95
No. of measured, independent and observed [I > 2σ(I)] reflections	35813, 4940, 3778
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.146, 1.10
No. of reflections	4940
No. of parameters	236
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.26
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1530646

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617001845/hb4120sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617001845/hb4120Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617001845/hb4120Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-(3-Methylphenyl)-3-[(3-methyl-5-phenyl-1H-pyrazol-1-yl)methyl]-4,5-dihydro-1H-1,2,4-triazole-5-thione top

Crystal data top

C₂₀H₁₉N₅S	F(000) = 760
M_r = 361.46	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9947 reflections
a = 8.3386 (5) Å	θ = 2.6–27.4°
b = 15.5969 (9) Å	µ = 0.18 mm⁻¹
c = 14.9334 (8) Å	T = 296 K
β = 99.834 (1)°	Block, colourless
V = 1913.65 (19) Å³	0.46 × 0.39 × 0.26 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	4940 independent reflections
Radiation source: fine-focus sealed tube	3778 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.3333 pixels mm^-1	θ_max = 28.7°, θ_min = 1.9°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −21→20
T_min = 0.87, T_max = 0.95	l = −20→20
35813 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.0824P)² + 0.1767P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
4940 reflections	Δρ_max = 0.31 e Å⁻³
236 parameters	Δρ_min = −0.26 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	0.08990 (6)	0.93018 (3)	0.76368 (3)	0.0686 (2)
N1	0.07577 (12)	0.84839 (7)	0.60041 (7)	0.0418 (3)
N2	−0.11285 (14)	0.92049 (8)	0.50918 (9)	0.0530 (4)
N3	−0.08851 (14)	0.95325 (8)	0.59569 (8)	0.0512 (4)
N4	0.15498 (13)	0.80095 (7)	0.40792 (7)	0.0472 (3)
N5	0.22539 (14)	0.87806 (8)	0.39760 (8)	0.0509 (4)
C1	0.02584 (16)	0.91209 (8)	0.65356 (10)	0.0466 (4)
C2	−0.01244 (15)	0.85699 (8)	0.51410 (9)	0.0441 (4)
C3	0.20542 (14)	0.78874 (8)	0.63013 (8)	0.0402 (3)
C4	0.36005 (15)	0.80791 (9)	0.61541 (9)	0.0472 (4)
C5	0.48769 (17)	0.75124 (11)	0.64334 (10)	0.0533 (4)
C6	0.45477 (19)	0.67623 (10)	0.68636 (10)	0.0575 (5)
C7	0.29975 (19)	0.65818 (9)	0.70153 (11)	0.0587 (5)
C8	0.17328 (17)	0.71456 (9)	0.67361 (10)	0.0509 (4)
C9	0.6570 (2)	0.77113 (16)	0.62645 (17)	0.0902 (8)
C10	−0.00265 (16)	0.79791 (10)	0.43684 (10)	0.0519 (4)
C11	0.37196 (18)	0.85957 (10)	0.37764 (10)	0.0536 (4)
C12	0.3940 (2)	0.77082 (11)	0.37496 (11)	0.0591 (5)
C13	0.25369 (18)	0.73447 (9)	0.39460 (9)	0.0508 (4)
C14	0.4856 (2)	0.93002 (13)	0.36231 (15)	0.0772 (7)
C15	0.20869 (18)	0.64418 (9)	0.40348 (10)	0.0536 (4)
C16	0.3127 (2)	0.59089 (11)	0.46143 (13)	0.0693 (6)
C17	0.2728 (3)	0.50589 (13)	0.47188 (16)	0.0860 (8)
C18	0.1284 (3)	0.47360 (13)	0.42448 (17)	0.0864 (8)
C19	0.0251 (2)	0.52531 (13)	0.36800 (14)	0.0785 (7)
C20	0.0639 (2)	0.61012 (12)	0.35723 (11)	0.0656 (5)
H3	−0.14120	1.00240	0.60600	0.0610*
H4	0.37920	0.85890	0.58670	0.0570*
H6	0.53840	0.63750	0.70530	0.0690*
H7	0.28010	0.60760	0.73080	0.0700*
H8	0.06870	0.70260	0.68400	0.0610*
H9A	0.71600	0.71860	0.62370	0.1350*
H9B	0.71230	0.80610	0.67500	0.1350*
H9C	0.65040	0.80130	0.56990	0.1350*
H10A	−0.02350	0.73980	0.45480	0.0620*
H10B	−0.08650	0.81310	0.38600	0.0620*
H12	0.48540	0.74210	0.36240	0.0710*
H14A	0.59530	0.91340	0.38630	0.1160*
H14B	0.45870	0.98110	0.39250	0.1160*
H14C	0.47560	0.94090	0.29830	0.1160*
H16	0.40980	0.61260	0.49330	0.0830*
H17	0.34280	0.47050	0.51060	0.1030*
H18	0.10170	0.41630	0.43120	0.1040*
H19	−0.07210	0.50330	0.33660	0.0940*
H20	−0.00750	0.64490	0.31860	0.0790*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0942 (3)	0.0526 (3)	0.0590 (3)	−0.0063 (2)	0.0135 (2)	−0.0143 (2)
N1	0.0412 (5)	0.0361 (5)	0.0482 (6)	0.0022 (4)	0.0082 (4)	0.0000 (4)
N2	0.0463 (6)	0.0538 (7)	0.0604 (7)	0.0110 (5)	0.0133 (5)	0.0060 (5)
N3	0.0516 (6)	0.0418 (6)	0.0639 (7)	0.0090 (5)	0.0201 (5)	0.0011 (5)
N4	0.0472 (6)	0.0481 (6)	0.0462 (6)	0.0087 (5)	0.0078 (4)	−0.0016 (4)
N5	0.0524 (6)	0.0498 (7)	0.0513 (6)	0.0098 (5)	0.0114 (5)	0.0030 (5)
C1	0.0487 (7)	0.0339 (6)	0.0601 (8)	−0.0036 (5)	0.0179 (6)	−0.0014 (5)
C2	0.0378 (6)	0.0455 (7)	0.0495 (7)	0.0043 (5)	0.0089 (5)	0.0028 (5)
C3	0.0423 (6)	0.0348 (6)	0.0425 (6)	0.0004 (5)	0.0046 (5)	−0.0011 (4)
C4	0.0456 (7)	0.0466 (7)	0.0486 (7)	−0.0031 (5)	0.0062 (5)	0.0065 (5)
C5	0.0430 (7)	0.0669 (9)	0.0490 (7)	0.0044 (6)	0.0052 (5)	0.0031 (6)
C6	0.0579 (8)	0.0548 (8)	0.0562 (8)	0.0165 (7)	−0.0002 (6)	0.0037 (6)
C7	0.0686 (9)	0.0406 (7)	0.0651 (9)	0.0015 (7)	0.0061 (7)	0.0111 (6)
C8	0.0492 (7)	0.0417 (7)	0.0618 (8)	−0.0047 (6)	0.0097 (6)	0.0056 (6)
C9	0.0484 (9)	0.1214 (18)	0.1018 (15)	0.0083 (10)	0.0156 (9)	0.0256 (13)
C10	0.0438 (7)	0.0600 (8)	0.0504 (7)	0.0060 (6)	0.0035 (5)	−0.0050 (6)
C11	0.0536 (8)	0.0561 (8)	0.0528 (7)	0.0089 (6)	0.0136 (6)	0.0021 (6)
C12	0.0555 (8)	0.0613 (9)	0.0630 (9)	0.0152 (7)	0.0171 (7)	−0.0034 (7)
C13	0.0547 (8)	0.0513 (8)	0.0457 (7)	0.0122 (6)	0.0069 (6)	−0.0048 (5)
C14	0.0703 (11)	0.0725 (12)	0.0953 (14)	0.0010 (9)	0.0328 (10)	0.0082 (10)
C15	0.0619 (8)	0.0487 (8)	0.0504 (7)	0.0101 (6)	0.0099 (6)	−0.0078 (6)
C16	0.0652 (10)	0.0574 (9)	0.0821 (12)	0.0139 (8)	0.0035 (8)	−0.0019 (8)
C17	0.0882 (14)	0.0589 (11)	0.1089 (16)	0.0201 (10)	0.0110 (11)	0.0110 (10)
C18	0.0987 (15)	0.0530 (10)	0.1094 (16)	−0.0030 (10)	0.0233 (12)	−0.0076 (10)
C19	0.0836 (12)	0.0680 (11)	0.0808 (12)	−0.0094 (10)	0.0056 (9)	−0.0170 (9)
C20	0.0743 (10)	0.0635 (10)	0.0548 (8)	0.0051 (8)	−0.0011 (7)	−0.0083 (7)

Geometric parameters (Å, º) top

S1—C1	1.6641 (15)	C15—C20	1.390 (2)
N1—C1	1.3796 (17)	C15—C16	1.391 (2)
N1—C2	1.3771 (17)	C16—C17	1.382 (3)
N1—C3	1.4379 (16)	C17—C18	1.383 (3)
N2—N3	1.3717 (18)	C18—C19	1.362 (3)
N2—C2	1.2909 (18)	C19—C20	1.378 (3)
N3—C1	1.3367 (18)	C4—H4	0.9300
N4—N5	1.3586 (17)	C6—H6	0.9300
N4—C10	1.4527 (18)	C7—H7	0.9300
N4—C13	1.3595 (18)	C8—H8	0.9300
N5—C11	1.3380 (19)	C9—H9A	0.9600
C2—C10	1.490 (2)	C9—H9B	0.9600
C3—C4	1.3774 (17)	C9—H9C	0.9600
C3—C8	1.3753 (19)	C10—H10A	0.9700
N3—H3	0.9100	C10—H10B	0.9700
C4—C5	1.392 (2)	C12—H12	0.9300
C5—C9	1.508 (2)	C14—H14A	0.9600
C5—C6	1.385 (2)	C14—H14B	0.9600
C6—C7	1.379 (2)	C14—H14C	0.9600
C7—C8	1.382 (2)	C16—H16	0.9300
C11—C14	1.494 (2)	C17—H17	0.9300
C11—C12	1.398 (2)	C18—H18	0.9300
C12—C13	1.376 (2)	C19—H19	0.9300
C13—C15	1.469 (2)	C20—H20	0.9300

C1—N1—C2	107.63 (11)	C17—C18—C19	120.29 (19)
C1—N1—C3	124.98 (11)	C18—C19—C20	120.30 (18)
C2—N1—C3	127.24 (10)	C15—C20—C19	120.69 (16)
N3—N2—C2	104.00 (12)	C3—C4—H4	120.00
N2—N3—C1	113.86 (12)	C5—C4—H4	120.00
N5—N4—C10	119.55 (11)	C5—C6—H6	120.00
N5—N4—C13	111.99 (11)	C7—C6—H6	120.00
C10—N4—C13	128.30 (12)	C6—C7—H7	120.00
N4—N5—C11	105.27 (12)	C8—C7—H7	120.00
S1—C1—N1	127.82 (10)	C3—C8—H8	121.00
S1—C1—N3	129.10 (11)	C7—C8—H8	121.00
N1—C1—N3	103.06 (12)	C5—C9—H9A	109.00
N1—C2—N2	111.44 (12)	C5—C9—H9B	109.00
N1—C2—C10	124.99 (11)	C5—C9—H9C	109.00
N2—C2—C10	123.46 (13)	H9A—C9—H9B	109.00
N1—C3—C4	119.03 (11)	H9A—C9—H9C	109.00
N1—C3—C8	119.55 (11)	H9B—C9—H9C	110.00
C4—C3—C8	121.41 (12)	N4—C10—H10A	109.00
N2—N3—H3	118.00	N4—C10—H10B	109.00
C1—N3—H3	127.00	C2—C10—H10A	109.00
C3—C4—C5	120.21 (13)	C2—C10—H10B	109.00
C6—C5—C9	121.12 (16)	H10A—C10—H10B	108.00
C4—C5—C6	118.27 (13)	C11—C12—H12	127.00
C4—C5—C9	120.61 (16)	C13—C12—H12	127.00
C5—C6—C7	120.96 (14)	C11—C14—H14A	109.00
C6—C7—C8	120.60 (14)	C11—C14—H14B	109.00
C3—C8—C7	118.53 (13)	C11—C14—H14C	109.00
N4—C10—C2	112.47 (11)	H14A—C14—H14B	109.00
C12—C11—C14	129.35 (15)	H14A—C14—H14C	110.00
N5—C11—C14	120.20 (14)	H14B—C14—H14C	109.00
N5—C11—C12	110.45 (14)	C15—C16—H16	120.00
C11—C12—C13	106.33 (14)	C17—C16—H16	120.00
N4—C13—C12	105.96 (13)	C16—C17—H17	120.00
N4—C13—C15	123.20 (13)	C18—C17—H17	120.00
C12—C13—C15	130.82 (14)	C17—C18—H18	120.00
C13—C15—C16	119.15 (14)	C19—C18—H18	120.00
C16—C15—C20	118.49 (14)	C18—C19—H19	120.00
C13—C15—C20	122.35 (14)	C20—C19—H19	120.00
C15—C16—C17	120.45 (17)	C15—C20—H20	120.00
C16—C17—C18	119.8 (2)	C19—C20—H20	120.00

C2—N1—C1—S1	178.75 (11)	N2—C2—C10—N4	117.70 (14)
C2—N1—C1—N3	0.48 (14)	N1—C3—C4—C5	−179.89 (12)
C3—N1—C1—S1	−5.43 (19)	C8—C3—C4—C5	1.0 (2)
C3—N1—C1—N3	176.31 (11)	N1—C3—C8—C7	179.98 (13)
C1—N1—C2—N2	−0.05 (16)	C4—C3—C8—C7	−0.9 (2)
C1—N1—C2—C10	−176.41 (12)	C3—C4—C5—C6	−0.4 (2)
C3—N1—C2—N2	−175.76 (12)	C3—C4—C5—C9	179.21 (16)
C3—N1—C2—C10	7.9 (2)	C4—C5—C6—C7	−0.3 (2)
C1—N1—C3—C4	−93.20 (15)	C9—C5—C6—C7	−179.87 (17)
C1—N1—C3—C8	85.91 (16)	C5—C6—C7—C8	0.3 (2)
C2—N1—C3—C4	81.80 (16)	C6—C7—C8—C3	0.3 (2)
C2—N1—C3—C8	−99.09 (15)	N5—C11—C12—C13	−0.20 (18)
C2—N2—N3—C1	0.74 (15)	C14—C11—C12—C13	179.49 (17)
N3—N2—C2—N1	−0.39 (15)	C11—C12—C13—N4	0.06 (16)
N3—N2—C2—C10	176.03 (12)	C11—C12—C13—C15	−178.41 (14)
N2—N3—C1—S1	−179.00 (11)	N4—C13—C15—C16	−125.72 (16)
N2—N3—C1—N1	−0.76 (15)	N4—C13—C15—C20	53.1 (2)
C10—N4—N5—C11	175.47 (12)	C12—C13—C15—C16	52.5 (2)
C13—N4—N5—C11	−0.21 (15)	C12—C13—C15—C20	−128.71 (18)
N5—N4—C10—C2	−45.23 (16)	C13—C15—C16—C17	179.33 (17)
C13—N4—C10—C2	129.67 (14)	C20—C15—C16—C17	0.5 (3)
N5—N4—C13—C12	0.09 (15)	C13—C15—C20—C19	−179.33 (15)
N5—N4—C13—C15	178.71 (12)	C16—C15—C20—C19	−0.6 (2)
C10—N4—C13—C12	−175.12 (13)	C15—C16—C17—C18	−0.1 (3)
C10—N4—C13—C15	3.5 (2)	C16—C17—C18—C19	−0.4 (4)
N4—N5—C11—C12	0.25 (16)	C17—C18—C19—C20	0.3 (3)
N4—N5—C11—C14	−179.47 (14)	C18—C19—C20—C15	0.1 (3)
N1—C2—C10—N4	−66.37 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···N5ⁱ	0.91	1.99	2.8765 (18)	164

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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