Crystal structure of 4-amino-3-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Mague, J.T.; Mohamed, S.K.; Akkurt, M.; Albayati, M.R.

doi:10.1107/S205698901500938X

organic compounds

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Volume 71| Part 6| June 2015| Page o417

doi:10.1107/S205698901500938X

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Crystal structure of 4-amino-3-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1H-1,2,4-triazole-5(4H)-thione

Joel T. Mague,^a Shaaban K. Mohamed,^b,^c Mehmet Akkurt ^d and Mustafa R. Albayati ^e ^*

^aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^bFaculty of Science & Engineering, School of Healthcare Science, 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, and ^eKirkuk University, College of Education, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 May 2015; accepted 17 May 2015; online 23 May 2015)

In the title compound, C₁₂H₁₂N₆S, the dihedral angles between the central pyrazole ring and the pendant triazole and benzene rings are 68.01 (4) and 59.83 (9)°, respectively. In the crystal, molecules are linked by N—H⋯N and N—H⋯S hydrogen bonds, generating (10-1) sheets.

Keywords: crystal structure; aminotriazoles; hydrogen bonding.

CCDC reference: 1401505

1. Related literature

For the bio-activities of aminotriazoles, see: Jin et al. (2007 ); Joung et al. (2000 ). For aminotriazoles as block-building synthons, see: Curtis (2004 ).

2. Experimental

2.1. Crystal data

C₁₂H₁₂N₆S
M_r = 272.34
Monoclinic, P 2₁ /n
a = 11.3278 (4) Å
b = 8.3970 (3) Å
c = 15.4427 (5) Å
β = 109.053 (1)°
V = 1388.43 (8) Å³
Z = 4
Cu Kα radiation
μ = 2.04 mm⁻¹
T = 150 K
0.24 × 0.18 × 0.10 mm

2.2. Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2014 ) T_min = 0.77, T_max = 0.82
10355 measured reflections
2683 independent reflections
2515 reflections with I > 2σ(I)
R_int = 0.021

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.102
S = 1.09
2683 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1ⁱ	0.91	1.94	2.8429 (17)	169
N6—H6A⋯S1ⁱⁱ	0.91	2.55	3.4157 (13)	159
N6—H6B⋯N4ⁱⁱⁱ	0.91	2.43	3.0059 (18)	122
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT; 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 ).

Supporting information

CCDC reference: 1401505

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500938X/hb7427sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500938X/hb7427Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500938X/hb7427Isup3.cml

checkCIF report

Comment top

Amino-1,2,4-triazoles are known to be biologically active compounds (Jin et al., 2007). For example, the 5-amino-1,2,4- triazole itself has been used as the pesticide Amitrole (Joung et al., 2000) and 3,5-diamino-1,2,4-triazole (Guanazole) is an antitumor drug that inhibits ribonucleotide reductase and DNA synthesis. In addition, they play an important role as amidine type synthons in heterocyclic chemistry (Curtis, 2004) particularly fused ring systems, such as imidazo[1,2-b][1,2,4]triazole, imidazo[2,1-c][1,2,4]triazole, 1,2,4-triazolo[1,5-a]pyrimidine and 1,2,4-traizolo[1,5-a][1,3,5]triazine possessing variety of biological effects. In this context, we report in this study the synthesis and crystal structure of the title compound.

In the title compound (Fig. 1), the dihedral angle between the central 5-membered ring and its attached phenyl ring is 59.83 (5)° while the dihedral angle between the two 5-membered rings is 68.01 (4)°. In the crystal, the molecules form sheets lying parallel to (101) through N—H···N and N—H···S hydrogen bonds (Fig. 2 and Table 1).

Related literature top

For the bio-activities of aminotriazoles, see: Jin et al. (2007); Joung et al. (2000). For aminotriazoles as block-building synthons, see: Curtis (2004).

Experimental top

A mixture of 1 mmol (258 mg) of 5-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1,3,4-oxadiazole-2(3H)-thione and 2 ml of hydrazine in 30 ml ethanol was heated at 351 K for 6 h. On cooling, the solid product was filtered off, dried under vacuum and recrystallized from ethanol to afford colorless blocks of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); 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).

Figures top

	Fig. 1. The title molecule showing labeling scheme and 50% probability ellipsoids.
	Fig. 2. Packing viewed down the b axis. N—H···N and N—H···S hydrogen bonds are shown, respectively, as blue and purple dotted lines.

4-Amino-3-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₂H₁₂N₆S	F(000) = 568
M_r = 272.34	D_x = 1.303 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 11.3278 (4) Å	Cell parameters from 8668 reflections
b = 8.3970 (3) Å	θ = 4.3–72.3°
c = 15.4427 (5) Å	µ = 2.04 mm⁻¹
β = 109.053 (1)°	T = 150 K
V = 1388.43 (8) Å³	Block, colourless
Z = 4	0.24 × 0.18 × 0.10 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2683 independent reflections
Radiation source: INCOATEC IµS micro-focus source	2515 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 4.2°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2014)	k = −9→10
T_min = 0.77, T_max = 0.82	l = −19→19
10355 measured reflections

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)] = 0.036	Hydrogen site location: mixed
wR(F²) = 0.102	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0581P)² + 0.5187P] where P = (F_o² + 2F_c²)/3
2683 reflections	(Δ/σ)_max = 0.002
173 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₂H₁₂N₆S	V = 1388.43 (8) Å³
M_r = 272.34	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 11.3278 (4) Å	µ = 2.04 mm⁻¹
b = 8.3970 (3) Å	T = 150 K
c = 15.4427 (5) Å	0.24 × 0.18 × 0.10 mm
β = 109.053 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2683 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2014)	2515 reflections with I > 2σ(I)
T_min = 0.77, T_max = 0.82	R_int = 0.021
10355 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.09	Δρ_max = 0.36 e Å⁻³
2683 reflections	Δρ_min = −0.28 e Å⁻³
173 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. H-atoms attached to carbon

were placed in calculated positions (C—H = 0.95 - 0.98 Å) while those

attached to nitrogen were placed in locations derived from a difference

map and their parameters adjusted to give N—H = 0.91 Å. All were

included as riding contributions with isotropic displacement

parameters 1.2 - 1.5 times those of the attached atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	1.06212 (3)	0.49379 (4)	0.36297 (2)	0.02864 (14)
N1	0.52909 (11)	0.54447 (14)	0.29113 (8)	0.0249 (3)
N2	0.60148 (11)	0.41615 (13)	0.33081 (8)	0.0235 (3)
N3	0.86566 (11)	0.29657 (15)	0.28254 (8)	0.0263 (3)
H3A	0.9039	0.2256	0.2559	0.032*
N4	0.74091 (11)	0.27516 (15)	0.27154 (9)	0.0273 (3)
N5	0.81912 (11)	0.48358 (13)	0.35855 (8)	0.0205 (3)
N6	0.81859 (11)	0.61690 (14)	0.41236 (8)	0.0262 (3)
H6A	0.8704	0.5948	0.4699	0.031*
H6B	0.8512	0.6973	0.3878	0.031*
C1	0.60875 (14)	0.17810 (17)	0.42641 (9)	0.0251 (3)
C2	0.72215 (17)	0.1972 (2)	0.49645 (11)	0.0399 (4)
H2	0.7559	0.3009	0.5120	0.048*
C3	0.78631 (19)	0.0666 (2)	0.54370 (13)	0.0469 (5)
H3	0.8636	0.0807	0.5914	0.056*
C4	0.73738 (18)	−0.0845 (2)	0.52122 (12)	0.0392 (4)
H4	0.7808	−0.1744	0.5538	0.047*
C5	0.62567 (16)	−0.10472 (18)	0.45161 (11)	0.0344 (4)
H5	0.5927	−0.2088	0.4362	0.041*
C6	0.56078 (15)	0.02533 (18)	0.40384 (11)	0.0292 (3)
H6	0.4839	0.0102	0.3559	0.035*
C7	0.54349 (13)	0.31865 (17)	0.37531 (9)	0.0239 (3)
C8	0.43020 (14)	0.38690 (19)	0.36366 (10)	0.0287 (3)
H8	0.3670	0.3482	0.3862	0.034*
C9	0.42509 (14)	0.52643 (18)	0.31143 (10)	0.0262 (3)
C10	0.71675 (13)	0.39120 (16)	0.31857 (9)	0.0218 (3)
C11	0.91672 (13)	0.42285 (16)	0.33429 (9)	0.0222 (3)
C12	0.32313 (15)	0.6470 (2)	0.28071 (13)	0.0386 (4)
H12A	0.3481	0.7316	0.2466	0.058*
H12B	0.3074	0.6928	0.3343	0.058*
H12C	0.2469	0.5957	0.2411	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0210 (2)	0.0357 (2)	0.0290 (2)	−0.00344 (13)	0.00779 (15)	−0.00294 (13)
N1	0.0233 (6)	0.0232 (6)	0.0304 (6)	0.0020 (5)	0.0120 (5)	0.0040 (5)
N2	0.0235 (6)	0.0206 (6)	0.0301 (6)	0.0012 (4)	0.0136 (5)	0.0031 (4)
N3	0.0235 (6)	0.0263 (6)	0.0330 (6)	−0.0013 (5)	0.0145 (5)	−0.0075 (5)
N4	0.0242 (6)	0.0270 (6)	0.0340 (6)	−0.0030 (5)	0.0141 (5)	−0.0049 (5)
N5	0.0224 (6)	0.0193 (5)	0.0210 (5)	0.0013 (4)	0.0088 (5)	−0.0009 (4)
N6	0.0311 (7)	0.0225 (6)	0.0248 (6)	0.0018 (5)	0.0089 (5)	−0.0048 (4)
C1	0.0288 (7)	0.0241 (7)	0.0251 (7)	−0.0021 (5)	0.0125 (6)	0.0010 (5)
C2	0.0459 (10)	0.0302 (8)	0.0355 (8)	−0.0082 (7)	0.0019 (7)	0.0026 (6)
C3	0.0468 (11)	0.0443 (10)	0.0382 (9)	−0.0008 (8)	−0.0018 (8)	0.0085 (8)
C4	0.0500 (10)	0.0327 (9)	0.0369 (8)	0.0094 (7)	0.0168 (7)	0.0099 (6)
C5	0.0477 (10)	0.0223 (7)	0.0372 (8)	0.0004 (6)	0.0195 (7)	−0.0018 (6)
C6	0.0316 (8)	0.0262 (7)	0.0313 (8)	−0.0027 (6)	0.0122 (6)	−0.0033 (6)
C7	0.0258 (7)	0.0230 (7)	0.0242 (6)	−0.0061 (5)	0.0101 (5)	−0.0012 (5)
C8	0.0246 (7)	0.0313 (8)	0.0333 (7)	−0.0045 (6)	0.0136 (6)	0.0045 (6)
C9	0.0223 (7)	0.0283 (7)	0.0294 (7)	−0.0019 (5)	0.0104 (6)	0.0014 (6)
C10	0.0217 (7)	0.0208 (6)	0.0242 (6)	0.0001 (5)	0.0094 (5)	0.0018 (5)
C11	0.0244 (7)	0.0229 (7)	0.0207 (6)	0.0014 (5)	0.0091 (5)	0.0014 (5)
C12	0.0262 (8)	0.0422 (9)	0.0521 (10)	0.0079 (7)	0.0193 (7)	0.0143 (8)

Geometric parameters (Å, º) top

S1—C11	1.6697 (14)	C2—C3	1.384 (2)
N1—C9	1.3230 (19)	C2—H2	0.9500
N1—N2	1.3714 (16)	C3—C4	1.383 (3)
N2—C7	1.3670 (18)	C3—H3	0.9500
N2—C10	1.3949 (18)	C4—C5	1.377 (3)
N3—C11	1.3401 (18)	C4—H4	0.9500
N3—N4	1.3790 (17)	C5—C6	1.387 (2)
N3—H3A	0.9100	C5—H5	0.9500
N4—C10	1.2968 (18)	C6—H6	0.9500
N5—C10	1.3639 (18)	C7—C8	1.363 (2)
N5—C11	1.3759 (17)	C8—C9	1.413 (2)
N5—N6	1.3953 (15)	C8—H8	0.9500
N6—H6A	0.9101	C9—C12	1.492 (2)
N6—H6B	0.9099	C12—H12A	0.9800
C1—C2	1.392 (2)	C12—H12B	0.9800
C1—C6	1.392 (2)	C12—H12C	0.9800
C1—C7	1.477 (2)

C9—N1—N2	104.65 (11)	C4—C5—H5	119.6
C7—N2—N1	112.32 (11)	C6—C5—H5	119.6
C7—N2—C10	127.07 (12)	C5—C6—C1	119.77 (15)
N1—N2—C10	120.47 (11)	C5—C6—H6	120.1
C11—N3—N4	113.70 (11)	C1—C6—H6	120.1
C11—N3—H3A	127.7	C8—C7—N2	105.56 (12)
N4—N3—H3A	118.6	C8—C7—C1	133.80 (13)
C10—N4—N3	103.20 (11)	N2—C7—C1	120.55 (12)
C10—N5—C11	107.82 (11)	C7—C8—C9	106.58 (12)
C10—N5—N6	123.89 (11)	C7—C8—H8	126.7
C11—N5—N6	128.28 (12)	C9—C8—H8	126.7
N5—N6—H6A	107.0	N1—C9—C8	110.89 (13)
N5—N6—H6B	105.4	N1—C9—C12	120.25 (13)
H6A—N6—H6B	109.8	C8—C9—C12	128.85 (14)
C2—C1—C6	119.08 (14)	N4—C10—N5	112.16 (12)
C2—C1—C7	119.82 (13)	N4—C10—N2	124.53 (13)
C6—C1—C7	121.07 (13)	N5—C10—N2	123.26 (12)
C3—C2—C1	120.73 (16)	N3—C11—N5	103.12 (11)
C3—C2—H2	119.6	N3—C11—S1	129.55 (11)
C1—C2—H2	119.6	N5—C11—S1	127.32 (11)
C4—C3—C2	119.73 (16)	C9—C12—H12A	109.5
C4—C3—H3	120.1	C9—C12—H12B	109.5
C2—C3—H3	120.1	H12A—C12—H12B	109.5
C5—C4—C3	119.98 (16)	C9—C12—H12C	109.5
C5—C4—H4	120.0	H12A—C12—H12C	109.5
C3—C4—H4	120.0	H12B—C12—H12C	109.5
C4—C5—C6	120.70 (15)

C9—N1—N2—C7	0.12 (16)	N2—N1—C9—C8	−0.21 (16)
C9—N1—N2—C10	176.19 (12)	N2—N1—C9—C12	178.88 (14)
C11—N3—N4—C10	−0.45 (16)	C7—C8—C9—N1	0.23 (18)
C6—C1—C2—C3	−0.5 (3)	C7—C8—C9—C12	−178.76 (16)
C7—C1—C2—C3	−178.43 (16)	N3—N4—C10—N5	−0.20 (15)
C1—C2—C3—C4	0.0 (3)	N3—N4—C10—N2	−177.56 (12)
C2—C3—C4—C5	0.5 (3)	C11—N5—C10—N4	0.75 (15)
C3—C4—C5—C6	−0.4 (3)	N6—N5—C10—N4	179.53 (12)
C4—C5—C6—C1	−0.1 (2)	C11—N5—C10—N2	178.15 (12)
C2—C1—C6—C5	0.5 (2)	N6—N5—C10—N2	−3.1 (2)
C7—C1—C6—C5	178.45 (13)	C7—N2—C10—N4	64.2 (2)
N1—N2—C7—C8	0.02 (16)	N1—N2—C10—N4	−111.26 (16)
C10—N2—C7—C8	−175.74 (13)	C7—N2—C10—N5	−112.89 (16)
N1—N2—C7—C1	−176.94 (12)	N1—N2—C10—N5	71.66 (18)
C10—N2—C7—C1	7.3 (2)	N4—N3—C11—N5	0.88 (15)
C2—C1—C7—C8	−118.65 (19)	N4—N3—C11—S1	−178.60 (11)
C6—C1—C7—C8	63.4 (2)	C10—N5—C11—N3	−0.94 (14)
C2—C1—C7—N2	57.3 (2)	N6—N5—C11—N3	−179.65 (12)
C6—C1—C7—N2	−120.64 (15)	C10—N5—C11—S1	178.55 (10)
N2—C7—C8—C9	−0.14 (16)	N6—N5—C11—S1	−0.2 (2)
C1—C7—C8—C9	176.23 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.91	1.94	2.8429 (17)	169
N6—H6A···S1ⁱⁱ	0.91	2.55	3.4157 (13)	159
N6—H6B···N4ⁱⁱⁱ	0.91	2.43	3.0059 (18)	122

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1ⁱ	0.91	1.94	2.8429 (17)	169
N6—H6A···S1ⁱⁱ	0.91	2.55	3.4157 (13)	159
N6—H6B···N4ⁱⁱⁱ	0.91	2.43	3.0059 (18)	122

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

Acknowledgements

The support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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Volume 71| Part 6| June 2015| Page o417

doi:10.1107/S205698901500938X

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

Crystal structure of 4-amino-3-(3-methyl-5-phenyl-1H-pyrazol-1-yl)-1H-1,2,4-triazole-5(4H)-thione

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds