5-Amino-3-methyl-1-phenyl-1H-1,2,4-triazole.

In the title compound, C(9)H(10)N(4), the phenyl and triazole rings make a dihedral angle of 38.80 (2)°. N-H⋯N hydrogen bonds link the mol-ecules, forming centrosymmetric R(2) (2)(8) rings; these rings are inter-connected through a C(5) chain, building up a zigzag layer parallel to the (100) plane.

Related literature

For related literature, see: Altman & Solomost (1993 ▶); Genady & Gabel (2003 ▶); Kanazawa et al. (1988 ▶); Karanik et al. (2003 ▶); Hashimoto et al. (1990 ▶); Allouch et al. (2004 ▶). For a discussion of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶).

Experimental

Crystal data

C9H10N4

M = 174.21

Monoclinic,

a = 8.5110 (5) Å

b = 11.2490 (8) Å

c = 10.1048 (7) Å

β = 101.866 (4)°

V = 946.76 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 (7) K

0.49 × 0.14 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.984, T max = 0.997

16028 measured reflections

3882 independent reflections

1997 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.148

S = 0.94

3882 reflections

124 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005801/dn2319sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005801/dn2319Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H10N4	F000 = 368
Mr = 174.21	Dx = 1.222 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2898 reflections
a = 8.5110 (5) Å	θ = 2.5–23.3º
b = 11.2490 (8) Å	µ = 0.08 mm−1
c = 10.1048 (7) Å	T = 296 (7) K
β = 101.866 (4)º	Prism, colourless
V = 946.76 (11) Å3	0.49 × 0.14 × 0.08 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3882 independent reflections
Radiation source: sealed tube	1997 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 296(2) K	θmax = 34.4º
φ and ω scans	θmin = 3.0º
Absorption correction: multi-scan(SADABS; Bruker, 1998)	h = −11→13
Tmin = 0.984, Tmax = 0.997	k = −17→17
16028 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.148	w = 1/[σ2(Fo2) + (0.0699P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
3882 reflections	Δρmax = 0.19 e Å−3
124 parameters	Δρmin = −0.16 e Å−3
3 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1	0.22326 (10)	0.20008 (8)	0.83687 (9)	0.0445 (2)
N2	0.28380 (11)	0.22738 (9)	0.72310 (10)	0.0530 (3)
N3	0.43302 (11)	0.08529 (9)	0.84645 (9)	0.0500 (3)
N4	0.29094 (12)	0.06921 (9)	1.02612 (10)	0.0528 (3)
H4A	0.3772 (12)	0.0290 (10)	1.0662 (12)	0.063*
H4B	0.2503 (14)	0.1219 (9)	1.0797 (11)	0.063*
C4	0.08173 (12)	0.25677 (10)	0.85950 (12)	0.0454 (3)
C3	0.31616 (12)	0.11612 (9)	0.90899 (11)	0.0424 (3)
C2	0.40669 (14)	0.15538 (11)	0.73467 (12)	0.0535 (3)
C9	−0.03152 (14)	0.19287 (12)	0.90944 (15)	0.0606 (3)
H9	−0.0159	0.1124	0.9286	0.073*
C5	0.05851 (16)	0.37569 (12)	0.82934 (14)	0.0663 (4)
H5	0.1354	0.4193	0.7968	0.080*
C1	0.51079 (17)	0.15076 (16)	0.63304 (15)	0.0792 (5)
H1A	0.5936	0.0925	0.6601	0.119*	0.50
H1B	0.5588	0.2273	0.6270	0.119*	0.50
H1C	0.4471	0.1295	0.5464	0.119*	0.50
H1D	0.4727	0.2070	0.5623	0.119*	0.50
H1E	0.5076	0.0722	0.5953	0.119*	0.50
H1F	0.6192	0.1700	0.6760	0.119*	0.50
C7	−0.19460 (19)	0.36600 (17)	0.89769 (18)	0.0921 (6)
H7	−0.2890	0.4028	0.9085	0.111*
C6	−0.0814 (2)	0.42885 (14)	0.84843 (18)	0.0877 (5)
H6	−0.0991	0.5089	0.8274	0.105*
C8	−0.16821 (16)	0.24917 (14)	0.93076 (18)	0.0797 (5)
H8	−0.2428	0.2072	0.9679	0.096*

	U11	U22	U33	U12	U13	U23
N1	0.0431 (4)	0.0488 (5)	0.0457 (5)	0.0065 (4)	0.0189 (4)	0.0059 (4)
N2	0.0492 (5)	0.0649 (6)	0.0499 (6)	0.0084 (4)	0.0218 (5)	0.0126 (5)
N3	0.0474 (5)	0.0574 (6)	0.0487 (6)	0.0104 (4)	0.0181 (4)	0.0014 (4)
N4	0.0584 (6)	0.0544 (6)	0.0507 (6)	0.0157 (5)	0.0228 (5)	0.0088 (5)
C4	0.0414 (5)	0.0509 (6)	0.0457 (6)	0.0077 (4)	0.0130 (5)	0.0019 (5)
C3	0.0439 (5)	0.0418 (6)	0.0437 (6)	0.0034 (4)	0.0140 (5)	−0.0003 (5)
C2	0.0480 (6)	0.0669 (7)	0.0500 (7)	0.0048 (5)	0.0200 (5)	0.0064 (6)
C9	0.0476 (6)	0.0612 (8)	0.0777 (9)	0.0036 (5)	0.0243 (6)	0.0070 (7)
C5	0.0711 (8)	0.0611 (8)	0.0754 (10)	0.0174 (6)	0.0353 (7)	0.0164 (7)
C1	0.0679 (8)	0.1133 (12)	0.0673 (10)	0.0214 (8)	0.0392 (7)	0.0151 (8)
C7	0.0709 (9)	0.1057 (13)	0.1108 (14)	0.0396 (9)	0.0445 (9)	0.0214 (10)
C6	0.0926 (11)	0.0767 (10)	0.1056 (13)	0.0420 (8)	0.0481 (10)	0.0290 (9)
C8	0.0534 (8)	0.0923 (11)	0.1032 (12)	0.0100 (7)	0.0385 (8)	0.0146 (9)

N1—C3	1.3459 (14)	C5—C6	1.3811 (18)
N1—N2	1.3874 (11)	C5—H5	0.9300
N1—C4	1.4224 (12)	C1—H1A	0.9600
N2—C2	1.3090 (14)	C1—H1B	0.9600
N3—C3	1.3294 (12)	C1—H1C	0.9600
N3—C2	1.3577 (15)	C1—H1D	0.9600
N4—C3	1.3528 (14)	C1—H1E	0.9600
N4—H4A	0.886 (8)	C1—H1F	0.9600
N4—H4B	0.917 (8)	C7—C8	1.363 (2)
C4—C5	1.3773 (17)	C7—C6	1.369 (2)
C4—C9	1.3785 (15)	C7—H7	0.9300
C2—C1	1.4888 (15)	C6—H6	0.9300
C9—C8	1.3799 (17)	C8—H8	0.9300
C9—H9	0.9300
C3—N1—N2	109.09 (7)	H1A—C1—H1C	109.5
C3—N1—C4	130.56 (8)	H1B—C1—H1C	109.5
N2—N1—C4	120.33 (9)	C2—C1—H1D	109.5
C2—N2—N1	102.42 (9)	H1A—C1—H1D	141.1
C3—N3—C2	103.43 (9)	H1B—C1—H1D	56.3
C3—N4—H4A	109.5 (8)	H1C—C1—H1D	56.3
C3—N4—H4B	114.3 (8)	C2—C1—H1E	109.5
H4A—N4—H4B	115.9 (11)	H1A—C1—H1E	56.3
C5—C4—C9	120.55 (10)	H1B—C1—H1E	141.1
C5—C4—N1	119.18 (9)	H1C—C1—H1E	56.3
C9—C4—N1	120.27 (10)	H1D—C1—H1E	109.5
N3—C3—N1	109.84 (9)	C2—C1—H1F	109.5
N3—C3—N4	125.66 (10)	H1A—C1—H1F	56.3
N1—C3—N4	124.49 (9)	H1B—C1—H1F	56.3
N2—C2—N3	115.20 (9)	H1C—C1—H1F	141.1
N2—C2—C1	122.54 (11)	H1D—C1—H1F	109.5
N3—C2—C1	122.26 (11)	H1E—C1—H1F	109.5
C4—C9—C8	119.55 (13)	C8—C7—C6	119.63 (12)
C4—C9—H9	120.2	C8—C7—H7	120.2
C8—C9—H9	120.2	C6—C7—H7	120.2
C4—C5—C6	118.57 (12)	C7—C6—C5	121.25 (14)
C4—C5—H5	120.7	C7—C6—H6	119.4
C6—C5—H5	120.7	C5—C6—H6	119.4
C2—C1—H1A	109.5	C7—C8—C9	120.39 (13)
C2—C1—H1B	109.5	C7—C8—H8	119.8
H1A—C1—H1B	109.5	C9—C8—H8	119.8
C2—C1—H1C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4A···N3i	0.886 (8)	2.110 (8)	2.9923 (13)	173.1 (12)
N4—H4B···N2ii	0.917 (8)	2.210 (10)	3.0415 (14)	150.4 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4A⋯N3i	0.886 (8)	2.110 (8)	2.9923 (13)	173.1 (12)
N4—H4B⋯N2ii	0.917 (8)	2.210 (10)	3.0415 (14)	150.4 (10)

Symmetry codes: (i) ; (ii) .