5-Amino-3-(4H-1,2,4-triazol-4-yl)-1H-1,2,4-triazole.

The asymmetric unit of the title compound, C(4)H(5)N(7), comprises two independent but virtually superimposable mol-ecules. Each mol-ecule is planar with the dihedral angles between the five-membered rings being 2.8 (3) and 2.1 (3)°. The crystal structure is formed by an extensive network of relatively strong N-H⋯N hydrogen-bond inter-actions. Individual mol-ecules are arranged into supra-molecular zigzag chains running parallel to [001] by way of the strongest N-H⋯N inter-actions. Adjacent chains are inter-connected by rather long (D⋯A distances range from ca 3.00 to 3.03 Å) but highly directional (inter-action angles above ca 173°) hydrogen bonds forming a supra-molecular layer in the bc plane.

Related literature

For the synthesis of 1-butyl-3-methyl­imidazolium bromide and 1,2-diformyl­hydrazine, see: Liu et al. (2007 ▶); Parnham & Morris (2006 ▶). For the use of triazole mol­ecules, see: Wang et al. (2012 ▶); Zhang et al. (2009 ▶). For previous research studies on crystal engineering approaches, see: Fernandes et al. (2011 ▶); Silva et al. (2011 ▶); Amarante et al. (2009 ▶); Paz & Klinowski (2007 ▶). For graph-set notation, see: Grell et al. (1999 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C4H5N7

M = 151.15

Monoclinic,

a = 13.765 (3) Å

b = 5.9378 (12) Å

c = 16.635 (4) Å

β = 112.914 (12)°

V = 1252.4 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.10 × 0.05 × 0.03 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.988, T max = 0.996

8003 measured reflections

2192 independent reflections

975 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.226

S = 0.96

2192 reflections

217 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034691/tk5136sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034691/tk5136Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034691/tk5136Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536812034691/tk5136Isup4.cml

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

C4H5N7	F(000) = 624
Mr = 151.15	Dx = 1.603 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 823 reflections
a = 13.765 (3) Å	θ = 2.7–21.7°
b = 5.9378 (12) Å	µ = 0.12 mm−1
c = 16.635 (4) Å	T = 293 K
β = 112.914 (12)°	Prism, yellow
V = 1252.4 (5) Å3	0.10 × 0.05 × 0.03 mm
Z = 8

Bruker X8 Kappa CCD APEXII diffractometer	2192 independent reflections
Radiation source: fine-focus sealed tube	975 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.079
ω / φ scans	θmax = 25.0°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −16→16
Tmin = 0.988, Tmax = 0.996	k = −7→5
8003 measured reflections	l = −19→19

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.226	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.1189P)2] where P = (Fo2 + 2Fc2)/3
2192 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.52 e Å−3
8 restraints	Δρmin = −0.36 e Å−3

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
N1	0.6176 (4)	−0.3457 (6)	−0.1686 (3)	0.0465 (13)
H1B	0.625 (4)	−0.477 (4)	−0.140 (3)	0.070*
H1A	0.625 (4)	−0.341 (7)	−0.2198 (16)	0.070*
N2	0.6244 (3)	0.0473 (7)	−0.1487 (3)	0.0431 (12)
H2	0.624 (4)	0.106 (9)	−0.1987 (18)	0.065*
N4	0.6274 (3)	0.2015 (6)	−0.0855 (3)	0.0443 (12)
C2	0.6268 (4)	0.0647 (8)	−0.0238 (3)	0.0346 (12)
N3	0.6228 (3)	−0.1582 (6)	−0.0393 (2)	0.0326 (10)
C1	0.6217 (4)	−0.1618 (8)	−0.1201 (3)	0.0368 (12)
N6	0.6346 (3)	0.1685 (7)	0.1884 (3)	0.0477 (12)
N7	0.6317 (3)	0.3877 (7)	0.1576 (3)	0.0493 (12)
C3	0.6290 (4)	0.3720 (8)	0.0783 (3)	0.0449 (14)
H3	0.6272	0.4936	0.0426	0.054*
N5	0.6292 (3)	0.1502 (6)	0.0556 (2)	0.0339 (10)
C4	0.6328 (4)	0.0325 (9)	0.1264 (3)	0.0420 (13)
H4	0.6338	−0.1238	0.1302	0.050*
N10	0.6263 (3)	0.2101 (6)	0.3519 (3)	0.0417 (12)
H10	0.636 (4)	0.166 (9)	0.3037 (19)	0.063*
N11	0.6323 (3)	0.0579 (6)	0.4167 (3)	0.0383 (11)
C6	0.6227 (3)	0.1927 (7)	0.4747 (3)	0.0312 (11)
N9	0.6124 (3)	0.4162 (6)	0.4575 (3)	0.0350 (10)
C5	0.6144 (4)	0.4198 (8)	0.3774 (3)	0.0341 (12)
N14	0.6344 (3)	−0.1263 (7)	0.6590 (3)	0.0441 (11)
N13	0.6262 (3)	0.0938 (7)	0.6861 (3)	0.0487 (12)
C7	0.6202 (4)	0.2269 (8)	0.6221 (3)	0.0440 (14)
H7	0.6136	0.3827	0.6229	0.053*
N12	0.6250 (3)	0.1088 (6)	0.5547 (2)	0.0342 (10)
C8	0.6339 (4)	−0.1094 (8)	0.5814 (3)	0.0411 (13)
H8	0.6390	−0.2311	0.5480	0.049*
N8	0.6036 (4)	0.6025 (7)	0.3278 (3)	0.0509 (13)
H8A	0.605 (4)	0.589 (7)	0.2746 (15)	0.076*
H8B	0.615 (4)	0.737 (4)	0.355 (3)	0.076*

	U11	U22	U33	U12	U13	U23
N1	0.083 (3)	0.031 (2)	0.035 (3)	0.001 (2)	0.033 (3)	−0.005 (2)
N2	0.084 (3)	0.030 (2)	0.026 (3)	−0.003 (2)	0.032 (3)	−0.001 (2)
N4	0.083 (3)	0.033 (2)	0.028 (3)	−0.001 (2)	0.033 (2)	0.000 (2)
C2	0.045 (3)	0.036 (3)	0.026 (3)	0.004 (2)	0.017 (3)	−0.002 (2)
N3	0.051 (3)	0.030 (2)	0.022 (2)	0.0005 (17)	0.020 (2)	0.0000 (17)
C1	0.050 (3)	0.036 (3)	0.030 (3)	0.001 (2)	0.022 (3)	−0.001 (2)
N6	0.075 (3)	0.051 (3)	0.025 (3)	0.007 (2)	0.028 (2)	−0.002 (2)
N7	0.066 (3)	0.044 (3)	0.044 (3)	−0.008 (2)	0.028 (3)	−0.008 (2)
C3	0.067 (4)	0.042 (3)	0.030 (3)	−0.005 (3)	0.022 (3)	−0.011 (2)
N5	0.052 (3)	0.035 (2)	0.021 (3)	0.0012 (19)	0.022 (2)	−0.0004 (18)
C4	0.059 (4)	0.045 (3)	0.027 (3)	0.005 (2)	0.022 (3)	0.003 (3)
N10	0.073 (3)	0.032 (3)	0.029 (3)	0.004 (2)	0.029 (3)	0.004 (2)
N11	0.067 (3)	0.031 (2)	0.023 (2)	−0.0016 (19)	0.024 (2)	−0.0013 (19)
C6	0.043 (3)	0.033 (3)	0.022 (3)	0.000 (2)	0.017 (2)	0.002 (2)
N9	0.055 (3)	0.029 (2)	0.026 (2)	0.0003 (18)	0.021 (2)	−0.0082 (18)
C5	0.050 (3)	0.028 (3)	0.028 (3)	0.001 (2)	0.020 (3)	0.000 (2)
N14	0.061 (3)	0.045 (3)	0.030 (3)	0.002 (2)	0.022 (2)	0.006 (2)
N13	0.073 (3)	0.048 (3)	0.029 (3)	−0.002 (2)	0.024 (2)	0.003 (2)
C7	0.069 (4)	0.038 (3)	0.033 (3)	−0.001 (2)	0.029 (3)	0.000 (3)
N12	0.052 (3)	0.030 (2)	0.024 (3)	−0.0001 (18)	0.020 (2)	−0.0002 (18)
C8	0.059 (4)	0.039 (3)	0.032 (3)	0.003 (2)	0.026 (3)	0.004 (2)
N8	0.097 (4)	0.030 (2)	0.036 (3)	0.001 (2)	0.037 (3)	0.002 (2)

N1—C1	1.345 (6)	N10—C5	1.346 (6)
N1—H1B	0.900 (5)	N10—N11	1.385 (5)
N1—H1A	0.899 (5)	N10—H10	0.901 (5)
N2—C1	1.335 (6)	N11—C6	1.299 (5)
N2—N4	1.382 (5)	C6—N9	1.353 (5)
N2—H2	0.899 (5)	C6—N12	1.410 (5)
N4—C2	1.312 (6)	N9—C5	1.344 (6)
C2—N3	1.346 (5)	C5—N8	1.336 (6)
C2—N5	1.403 (5)	N14—C8	1.293 (6)
N3—C1	1.337 (6)	N14—N13	1.401 (5)
N6—C4	1.303 (6)	N13—C7	1.302 (6)
N6—N7	1.394 (6)	C7—N12	1.346 (6)
N7—C3	1.307 (6)	C7—H7	0.9300
C3—N5	1.370 (6)	N12—C8	1.360 (6)
C3—H3	0.9300	C8—H8	0.9300
N5—C4	1.353 (6)	N8—H8A	0.899 (5)
C4—H4	0.9300	N8—H8B	0.900 (5)
C1—N1—H1B	114 (3)	C5—N10—N11	109.6 (4)
C1—N1—H1A	123 (3)	C5—N10—H10	129 (4)
H1B—N1—H1A	120 (4)	N11—N10—H10	121 (4)
C1—N2—N4	110.0 (4)	C6—N11—N10	100.6 (4)
C1—N2—H2	134 (4)	N11—C6—N9	118.7 (4)
N4—N2—H2	116 (4)	N11—C6—N12	120.8 (4)
C2—N4—N2	100.2 (4)	N9—C6—N12	120.5 (4)
N4—C2—N3	118.1 (4)	C5—N9—C6	100.6 (4)
N4—C2—N5	120.5 (4)	N8—C5—N9	125.8 (4)
N3—C2—N5	121.4 (4)	N8—C5—N10	123.7 (4)
C1—N3—C2	101.1 (4)	N9—C5—N10	110.5 (4)
N2—C1—N3	110.6 (4)	C8—N14—N13	106.2 (4)
N2—C1—N1	122.8 (5)	C7—N13—N14	106.9 (4)
N3—C1—N1	126.6 (5)	N13—C7—N12	110.9 (4)
C4—N6—N7	107.4 (4)	N13—C7—H7	124.5
C3—N7—N6	106.8 (4)	N12—C7—H7	124.5
N7—C3—N5	110.1 (5)	C7—N12—C8	104.6 (4)
N7—C3—H3	124.9	C7—N12—C6	127.8 (4)
N5—C3—H3	124.9	C8—N12—C6	127.6 (4)
C4—N5—C3	105.1 (4)	N14—C8—N12	111.4 (4)
C4—N5—C2	127.7 (4)	N14—C8—H8	124.3
C3—N5—C2	127.2 (4)	N12—C8—H8	124.3
N6—C4—N5	110.6 (4)	C5—N8—H8A	120 (3)
N6—C4—H4	124.7	C5—N8—H8B	117 (3)
N5—C4—H4	124.7	H8A—N8—H8B	120 (4)
C1—N2—N4—C2	0.4 (5)	C5—N10—N11—C6	0.3 (5)
N2—N4—C2—N3	−0.7 (6)	N10—N11—C6—N9	−0.9 (6)
N2—N4—C2—N5	−179.9 (4)	N10—N11—C6—N12	−179.6 (4)
N4—C2—N3—C1	0.7 (6)	N11—C6—N9—C5	1.0 (6)
N5—C2—N3—C1	180.0 (4)	N12—C6—N9—C5	179.8 (4)
N4—N2—C1—N3	0.0 (6)	C6—N9—C5—N8	177.7 (5)
N4—N2—C1—N1	179.4 (4)	C6—N9—C5—N10	−0.7 (5)
C2—N3—C1—N2	−0.4 (5)	N11—N10—C5—N8	−178.2 (5)
C2—N3—C1—N1	−179.8 (5)	N11—N10—C5—N9	0.3 (5)
C4—N6—N7—C3	−0.4 (5)	C8—N14—N13—C7	0.7 (5)
N6—N7—C3—N5	0.4 (6)	N14—N13—C7—N12	−0.6 (6)
N7—C3—N5—C4	−0.3 (5)	N13—C7—N12—C8	0.3 (6)
N7—C3—N5—C2	180.0 (4)	N13—C7—N12—C6	−178.9 (4)
N4—C2—N5—C4	−177.5 (5)	N11—C6—N12—C7	177.2 (4)
N3—C2—N5—C4	3.3 (7)	N9—C6—N12—C7	−1.5 (7)
N4—C2—N5—C3	2.1 (7)	N11—C6—N12—C8	−1.8 (7)
N3—C2—N5—C3	−177.1 (4)	N9—C6—N12—C8	179.4 (4)
N7—N6—C4—N5	0.2 (5)	N13—N14—C8—N12	−0.5 (5)
C3—N5—C4—N6	0.0 (5)	C7—N12—C8—N14	0.2 (5)
C2—N5—C4—N6	179.7 (4)	C6—N12—C8—N14	179.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N14i	0.90 (1)	2.43 (2)	3.239 (6)	150 (4)
N1—H1B···N4ii	0.90 (1)	2.11 (1)	3.002 (6)	173 (5)
N2—H2···N13i	0.90 (1)	1.93 (2)	2.772 (6)	155 (5)
N8—H8A···N7	0.90 (1)	2.43 (2)	3.264 (6)	154 (4)
N8—H8B···N11iii	0.90 (1)	2.14 (1)	3.034 (6)	176 (5)
N10—H10···N6	0.90 (1)	1.91 (2)	2.777 (6)	161 (5)

π-π interaction	d(Cg···Cg)
Cg(1)···Cg(2)i	3.580 (3)
Cg(3)···Cg(4)ii	3.700 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N14i	0.90 (1)	2.43 (2)	3.239 (6)	150 (4)
N1—H1B⋯N4ii	0.90 (1)	2.11 (1)	3.002 (6)	173 (5)
N2—H2⋯N13i	0.90 (1)	1.93 (2)	2.772 (6)	155 (5)
N8—H8A⋯N7	0.90 (1)	2.43 (2)	3.264 (6)	154 (4)
N8—H8B⋯N11iii	0.90 (1)	2.14 (1)	3.034 (6)	176 (5)
N10—H10⋯N6	0.90 (1)	1.91 (2)	2.777 (6)	161 (5)

Symmetry codes: (i) ; (ii) ; (iii) .