5-Amino-1-(1,5-di­methyl-1H-pyrazol-4-yl­carbonyl)-3-methyl­sulfanyl-1H-1,2,4-triazole

In the title compound, C₉H₁₂N₆OS, the pyrazole and triazole rings are nearly coplanar, forming a dihedral angle of 6.50 (9)°. There are N—H...N intermolecular hydrogen-bond interactions in the crystal structure, providing stabilization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.043
• wR factor = 0.138
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

5-Amino-1-(1,5-dimethyl-1H-pyrazol-4-ylcarbonyl)-3-methylsulfanyl- 1H-1,2,4-triazole

Crystal data

C9H12N6OS	F(000) = 528
Mr = 252.31	Dx = 1.458 Mg m^−3
Monoclinic, P21/n	Melting point: 514 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.642 (5) Å	Cell parameters from 2811 reflections
b = 10.100 (7) Å	θ = 2.4–27.8°
c = 15.25 (1) Å	µ = 0.28 mm^−1
β = 101.275 (8)°	T = 293 K
V = 1154.3 (13) Å^3	Prism, colourless
Z = 4	0.59 × 0.38 × 0.20 mm

Data collection

Bruker APEX II CCD area-detector diffractometer	2024 independent reflections
Radiation source: fine-focus sealed tube	1763 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.882, Tmax = 0.946	k = −12→10
5982 measured reflections	l = −18→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.08	w = 1/[σ^2(Fo^2) + (0.088P)^2 + 0.3815P] where P = (Fo^2 + 2Fc^2)/3
2024 reflections	(Δ/σ)max = 0.001
158 parameters	Δρmax = 0.29 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.10096 (9)	0.26001 (5)	0.73818 (4)	0.0513 (3)
O1	0.1850 (3)	0.14608 (17)	0.35938 (10)	0.0574 (5)
N1	0.3695 (3)	−0.23200 (17)	0.43843 (12)	0.0435 (5)
N2	0.3390 (3)	−0.23236 (18)	0.52346 (14)	0.0508 (5)
N3	0.1647 (2)	0.18127 (17)	0.50250 (10)	0.0377 (4)
N4	0.1752 (2)	0.14103 (17)	0.59131 (11)	0.0378 (4)
N5	0.0756 (2)	0.35432 (17)	0.57145 (11)	0.0419 (5)
N6	0.0819 (3)	0.3799 (2)	0.41826 (13)	0.0546 (5)
H6A	0.0146	0.4507	0.4224	0.082*
H6B	0.0287	0.3293	0.3731	0.082*
C1	0.2779 (3)	−0.1124 (2)	0.53426 (14)	0.0444 (5)
H1	0.2450	−0.0832	0.5865	0.053*
C2	0.4291 (4)	−0.3542 (2)	0.40298 (19)	0.0599 (7)
H2A	0.3311	−0.4152	0.3899	0.090*
H2B	0.5234	−0.3926	0.4464	0.090*
H2C	0.4721	−0.3354	0.3492	0.090*
C3	0.3601 (3)	−0.0933 (2)	0.30431 (15)	0.0496 (6)
H3A	0.4729	−0.1305	0.2985	0.074*
H3B	0.3605	0.0002	0.2929	0.074*
H3C	0.2664	−0.1346	0.2620	0.074*
C4	0.3301 (3)	−0.11662 (19)	0.39637 (13)	0.0365 (5)
C5	0.2687 (3)	−0.03366 (19)	0.45695 (13)	0.0354 (5)
C6	0.2056 (3)	0.1000 (2)	0.43473 (13)	0.0385 (5)
C7	0.1192 (3)	0.24681 (18)	0.62684 (14)	0.0376 (5)
C8	0.1448 (4)	0.0926 (2)	0.77486 (15)	0.0516 (6)
H8A	0.0566	0.0352	0.7410	0.077*
H8B	0.1403	0.0861	0.8372	0.077*
H8C	0.2611	0.0669	0.7661	0.077*
C9	0.1037 (3)	0.3110 (2)	0.49419 (13)	0.0396 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0844 (5)	0.0389 (4)	0.0334 (4)	0.0010 (3)	0.0184 (3)	−0.0047 (2)
O1	0.0905 (13)	0.0526 (10)	0.0314 (8)	0.0214 (9)	0.0173 (8)	0.0087 (7)
N1	0.0522 (11)	0.0371 (10)	0.0430 (11)	0.0027 (8)	0.0135 (9)	−0.0020 (7)
N2	0.0698 (14)	0.0411 (11)	0.0430 (11)	0.0044 (9)	0.0148 (9)	0.0051 (8)
N3	0.0501 (10)	0.0360 (9)	0.0277 (8)	0.0070 (7)	0.0095 (7)	0.0027 (7)
N4	0.0499 (10)	0.0375 (9)	0.0265 (8)	0.0041 (7)	0.0086 (7)	0.0014 (7)
N5	0.0536 (11)	0.0366 (9)	0.0362 (10)	0.0050 (8)	0.0102 (8)	0.0022 (7)
N6	0.0785 (14)	0.0464 (11)	0.0408 (11)	0.0176 (10)	0.0163 (10)	0.0093 (9)
C1	0.0596 (13)	0.0405 (12)	0.0343 (11)	0.0025 (10)	0.0124 (10)	0.0002 (9)
C2	0.0744 (17)	0.0391 (13)	0.0691 (17)	0.0065 (11)	0.0216 (14)	−0.0082 (12)
C3	0.0604 (14)	0.0522 (13)	0.0406 (12)	0.0051 (11)	0.0208 (10)	−0.0015 (10)
C4	0.0361 (10)	0.0376 (11)	0.0359 (11)	−0.0013 (8)	0.0077 (8)	−0.0015 (8)
C5	0.0380 (10)	0.0373 (11)	0.0308 (10)	−0.0001 (8)	0.0067 (8)	0.0004 (8)
C6	0.0450 (11)	0.0404 (11)	0.0312 (11)	0.0034 (9)	0.0097 (8)	0.0012 (8)
C7	0.0428 (12)	0.0349 (10)	0.0349 (11)	−0.0005 (8)	0.0065 (9)	0.0002 (8)
C8	0.0709 (15)	0.0465 (13)	0.0385 (12)	−0.0015 (11)	0.0134 (11)	0.0048 (10)
C9	0.0472 (12)	0.0370 (11)	0.0344 (10)	0.0065 (9)	0.0080 (9)	0.0037 (9)

Geometric parameters (Å, º)

S1—C7	1.736 (2)	N6—H6B	0.8900
S1—C8	1.791 (3)	C1—C5	1.412 (3)
O1—C6	1.221 (3)	C1—H1	0.9300
N1—C4	1.336 (3)	C2—H2A	0.9600
N1—N2	1.362 (3)	C2—H2B	0.9600
N1—C2	1.456 (3)	C2—H2C	0.9600
N2—C1	1.320 (3)	C3—C4	1.485 (3)
N3—C9	1.388 (3)	C3—H3A	0.9600
N3—N4	1.401 (2)	C3—H3B	0.9600
N3—C6	1.402 (3)	C3—H3C	0.9600
N4—C7	1.307 (3)	C4—C5	1.395 (3)
N5—C9	1.313 (3)	C5—C6	1.451 (3)
N5—C7	1.376 (3)	C8—H8A	0.9600
N6—C9	1.333 (3)	C8—H8B	0.9600
N6—H6A	0.8900	C8—H8C	0.9600
C7—S1—C8	100.79 (10)	C4—C3—H3C	109.5
C4—N1—N2	113.28 (17)	H3A—C3—H3C	109.5
C4—N1—C2	128.2 (2)	H3B—C3—H3C	109.5
N2—N1—C2	118.40 (19)	N1—C4—C5	106.22 (18)
C1—N2—N1	104.29 (17)	N1—C4—C3	122.03 (18)
C9—N3—N4	108.46 (15)	C5—C4—C3	131.69 (19)
C9—N3—C6	127.20 (17)	C4—C5—C1	104.27 (19)
N4—N3—C6	124.32 (17)	C4—C5—C6	122.93 (18)
C7—N4—N3	101.66 (16)	C1—C5—C6	132.74 (19)
C9—N5—C7	103.03 (18)	O1—C6—N3	117.65 (19)
C9—N6—H6A	109.5	O1—C6—C5	123.39 (19)
C9—N6—H6B	109.5	N3—C6—C5	118.96 (18)
H6A—N6—H6B	109.5	N4—C7—N5	116.75 (19)
N2—C1—C5	111.94 (19)	N4—C7—S1	124.30 (15)
N2—C1—H1	124.0	N5—C7—S1	118.94 (15)
C5—C1—H1	124.0	S1—C8—H8A	109.5
N1—C2—H2A	109.5	S1—C8—H8B	109.5
N1—C2—H2B	109.5	H8A—C8—H8B	109.5
H2A—C2—H2B	109.5	S1—C8—H8C	109.5
N1—C2—H2C	109.5	H8A—C8—H8C	109.5
H2A—C2—H2C	109.5	H8B—C8—H8C	109.5
H2B—C2—H2C	109.5	N5—C9—N6	126.2 (2)
C4—C3—H3A	109.5	N5—C9—N3	110.08 (17)
C4—C3—H3B	109.5	N6—C9—N3	123.68 (18)
H3A—C3—H3B	109.5
C4—N1—N2—C1	0.1 (3)	N4—N3—C6—C5	−2.1 (3)
C2—N1—N2—C1	−176.6 (2)	C4—C5—C6—O1	7.3 (3)
C9—N3—N4—C7	0.7 (2)	C1—C5—C6—O1	−169.5 (2)
C6—N3—N4—C7	−177.77 (19)	C4—C5—C6—N3	−173.12 (19)
N1—N2—C1—C5	−0.1 (3)	C1—C5—C6—N3	10.2 (3)
N2—N1—C4—C5	−0.1 (2)	N3—N4—C7—N5	−1.2 (2)
C2—N1—C4—C5	176.2 (2)	N3—N4—C7—S1	−179.97 (15)
N2—N1—C4—C3	177.6 (2)	C9—N5—C7—N4	1.2 (3)
C2—N1—C4—C3	−6.1 (3)	C9—N5—C7—S1	−179.93 (15)
N1—C4—C5—C1	0.0 (2)	C8—S1—C7—N4	−8.0 (2)
C3—C4—C5—C1	−177.3 (2)	C8—S1—C7—N5	173.27 (18)
N1—C4—C5—C6	−177.49 (18)	C7—N5—C9—N6	−179.3 (2)
C3—C4—C5—C6	5.1 (3)	C7—N5—C9—N3	−0.7 (2)
N2—C1—C5—C4	0.1 (3)	N4—N3—C9—N5	0.0 (2)
N2—C1—C5—C6	177.2 (2)	C6—N3—C9—N5	178.41 (19)
C9—N3—C6—O1	−0.6 (3)	N4—N3—C9—N6	178.7 (2)
N4—N3—C6—O1	177.57 (19)	C6—N3—C9—N6	−2.9 (4)
C9—N3—C6—C5	179.75 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6B···O1	0.89	2.23	2.695 (3)	112
N6—H6A···N5^i	0.89	2.09	2.961 (3)	163

Symmetry code: (i) −x, −y+1, −z+1.