5-[(2-Methyl-4-nitro-1H-imidazol-1-yl)meth-yl]-1,3,4-thia-diazol-2-amine.

In the title compound, C7H8N6O2S, the dihedral angle between the imidazole and thia-diazole rings is 70.86 (15)°. In the crystal, mol-ecules are linked into [10-1] chains by N-H⋯N hydrogen bonds, which incorporate centrosymmetric R 2 (2)(8) and R 2 (2)(18) loops. The chains are linked by C-H⋯O and C-H⋯N inter-actions, generating a three-dimensional network. Very weak π-π stacking [centroid-centroid distance = 3.901 (17) Å] is also observed.

Related literature

For biological background, see: Dogan et al. (2002 ▶); Frank & Kalluraya (2005 ▶); Mullican et al. (1993 ▶). For related structures, see: Zama et al. (2013 ▶); Yin et al. (2012 ▶).

Experimental

Crystal data

C7H8N6O2S

M = 240.26

Triclinic,

a = 7.8030 (15) Å

b = 8.2750 (16) Å

c = 8.3596 (16) Å

α = 100.945 (8)°

β = 92.379 (8)°

γ = 105.911 (7)°

V = 507.15 (17) Å3

Z = 2

Cu Kα radiation

μ = 2.86 mm−1

T = 296 K

0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.559, T max = 0.585

5433 measured reflections

1640 independent reflections

1560 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.084

wR(F 2) = 0.206

S = 1.10

1640 reflections

147 parameters

H-atom parameters constrained

Δρmax = 0.80 e Å−3

Δρmin = −0.65 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813030821/hb7159sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813030821/hb7159Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813030821/hb7159Isup3.cml

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

C7H8N6O2S	Z = 2
Mr = 240.26	F(000) = 248
Triclinic, P1	Dx = 1.573 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 7.8030 (15) Å	Cell parameters from 1640 reflections
b = 8.2750 (16) Å	θ = 5.4–65.5°
c = 8.3596 (16) Å	µ = 2.86 mm−1
α = 100.945 (8)°	T = 296 K
β = 92.379 (8)°	Block, red
γ = 105.911 (7)°	0.23 × 0.22 × 0.21 mm
V = 507.15 (17) Å3

Bruker X8 Proteum diffractometer	1640 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	1560 reflections with I > 2σ(I)
Helios multilayer optics monochromator	Rint = 0.038
Detector resolution: 10.7 pixels mm-1	θmax = 64.5°, θmin = 5.4°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→9
Tmin = 0.559, Tmax = 0.585	l = −9→9
5433 measured reflections

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)] = 0.084	H-atom parameters constrained
wR(F2) = 0.206	w = 1/[σ2(Fo2) + (0.170P)2 + 0.1569P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
1640 reflections	Δρmax = 0.80 e Å−3
147 parameters	Δρmin = −0.65 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.128 (15)

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 e.s.d.'s 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 > σ(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.

	x	y	z	Uiso*/Ueq
S1	0.07927 (9)	0.48240 (8)	0.72687 (8)	0.0272 (3)
O1	−0.3024 (4)	−0.0160 (4)	1.2300 (3)	0.0530 (10)
O2	−0.2117 (4)	−0.1962 (3)	1.0555 (4)	0.0520 (10)
N1	0.2714 (3)	0.3731 (3)	0.5159 (3)	0.0301 (8)
N2	0.1108 (3)	0.2446 (3)	0.4968 (3)	0.0292 (8)
N3	0.4148 (4)	0.6476 (3)	0.6733 (3)	0.0346 (9)
N4	−0.2299 (3)	0.1372 (3)	0.7565 (3)	0.0217 (7)
N5	−0.3183 (3)	0.1775 (3)	1.0046 (3)	0.0253 (8)
N6	−0.2558 (4)	−0.0653 (3)	1.0942 (3)	0.0327 (9)
C1	0.2758 (4)	0.5055 (4)	0.6315 (3)	0.0229 (8)
C2	−0.0004 (4)	0.2824 (3)	0.5963 (3)	0.0224 (8)
C3	−0.1855 (4)	0.1641 (4)	0.5939 (3)	0.0257 (9)
C4	−0.2020 (4)	0.0071 (3)	0.8234 (3)	0.0230 (8)
C5	−0.2577 (4)	0.0367 (3)	0.9743 (3)	0.0228 (8)
C6	−0.3017 (4)	0.2373 (3)	0.8694 (3)	0.0237 (8)
C7	−0.3577 (5)	0.3853 (4)	0.8382 (4)	0.0396 (11)
H3A	0.50960	0.65610	0.62280	0.0420*
H3B	0.40920	0.73040	0.75070	0.0420*
H3C	−0.27200	0.21210	0.54820	0.0310*
H3D	−0.19450	0.05410	0.52310	0.0310*
H4	−0.15570	−0.08100	0.77630	0.0280*
H7A	−0.48610	0.35570	0.82610	0.0600*
H7B	−0.31210	0.41570	0.73980	0.0600*
H7C	−0.31140	0.48100	0.92860	0.0600*

	U11	U22	U33	U12	U13	U23
S1	0.0282 (6)	0.0236 (6)	0.0256 (6)	0.0051 (4)	0.0134 (3)	−0.0037 (4)
O1	0.079 (2)	0.0551 (17)	0.0176 (12)	0.0078 (14)	0.0032 (11)	0.0072 (11)
O2	0.0665 (19)	0.0387 (15)	0.0623 (17)	0.0249 (13)	0.0124 (14)	0.0226 (13)
N1	0.0320 (14)	0.0244 (13)	0.0298 (14)	0.0055 (10)	0.0161 (10)	−0.0031 (10)
N2	0.0321 (14)	0.0231 (13)	0.0280 (13)	0.0044 (10)	0.0135 (11)	−0.0022 (10)
N3	0.0309 (15)	0.0277 (14)	0.0377 (16)	0.0028 (11)	0.0177 (11)	−0.0062 (11)
N4	0.0245 (12)	0.0199 (12)	0.0196 (12)	0.0057 (9)	0.0085 (9)	0.0012 (9)
N5	0.0274 (13)	0.0215 (13)	0.0225 (13)	0.0038 (10)	0.0102 (9)	−0.0031 (10)
N6	0.0326 (15)	0.0302 (15)	0.0294 (15)	−0.0002 (11)	−0.0024 (11)	0.0068 (11)
C1	0.0268 (15)	0.0227 (14)	0.0208 (14)	0.0090 (11)	0.0100 (11)	0.0040 (11)
C2	0.0298 (16)	0.0209 (14)	0.0169 (13)	0.0076 (12)	0.0079 (11)	0.0030 (10)
C3	0.0281 (16)	0.0284 (16)	0.0169 (14)	0.0037 (12)	0.0066 (11)	0.0013 (11)
C4	0.0233 (14)	0.0169 (14)	0.0263 (15)	0.0046 (11)	0.0043 (11)	0.0001 (11)
C5	0.0238 (14)	0.0194 (14)	0.0213 (14)	0.0018 (11)	0.0026 (11)	0.0015 (11)
C6	0.0234 (14)	0.0208 (14)	0.0256 (15)	0.0059 (11)	0.0116 (11)	0.0001 (11)
C7	0.046 (2)	0.0322 (17)	0.049 (2)	0.0214 (15)	0.0195 (16)	0.0104 (15)

S1—C1	1.739 (3)	N6—C5	1.430 (3)
S1—C2	1.735 (3)	N3—H3A	0.8600
O1—N6	1.236 (4)	N3—H3B	0.8600
O2—N6	1.215 (4)	C2—C3	1.503 (4)
N1—N2	1.384 (3)	C4—C5	1.352 (4)
N1—C1	1.308 (4)	C6—C7	1.471 (4)
N2—C2	1.286 (4)	C3—H3C	0.9700
N3—C1	1.340 (4)	C3—H3D	0.9700
N4—C3	1.459 (4)	C4—H4	0.9300
N4—C4	1.366 (4)	C7—H7A	0.9600
N4—C6	1.376 (4)	C7—H7B	0.9600
N5—C5	1.358 (4)	C7—H7C	0.9600
N5—C6	1.315 (3)
C1—S1—C2	86.83 (14)	N4—C4—C5	103.6 (2)
N2—N1—C1	112.7 (2)	N6—C5—C4	125.5 (3)
N1—N2—C2	112.9 (2)	N5—C5—N6	121.4 (2)
C3—N4—C4	124.6 (2)	N5—C5—C4	113.1 (2)
C3—N4—C6	127.0 (2)	N4—C6—N5	110.2 (2)
C4—N4—C6	108.3 (2)	N4—C6—C7	124.1 (2)
C5—N5—C6	104.7 (2)	N5—C6—C7	125.7 (3)
O1—N6—O2	124.2 (3)	N4—C3—H3C	109.00
O1—N6—C5	117.7 (3)	N4—C3—H3D	109.00
O2—N6—C5	118.1 (3)	C2—C3—H3C	109.00
C1—N3—H3B	120.00	C2—C3—H3D	109.00
H3A—N3—H3B	120.00	H3C—C3—H3D	108.00
C1—N3—H3A	120.00	N4—C4—H4	128.00
N1—C1—N3	124.6 (3)	C5—C4—H4	128.00
S1—C1—N3	122.1 (2)	C6—C7—H7A	109.00
S1—C1—N1	113.3 (2)	C6—C7—H7B	109.00
S1—C2—N2	114.3 (2)	C6—C7—H7C	109.00
S1—C2—C3	123.6 (2)	H7A—C7—H7B	110.00
N2—C2—C3	122.1 (2)	H7A—C7—H7C	109.00
N4—C3—C2	112.6 (2)	H7B—C7—H7C	109.00

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N1i	0.86	2.15	2.996 (4)	169
N3—H3B···N5ii	0.86	2.26	3.033 (4)	150
C3—H3D···O1iii	0.97	2.46	3.100 (4)	123
C4—H4···N2iv	0.93	2.51	3.296 (4)	142
C7—H7C···O2v	0.96	2.57	3.445 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N1i	0.86	2.15	2.996 (4)	169
N3—H3B⋯N5ii	0.86	2.26	3.033 (4)	150
C3—H3D⋯O1iii	0.97	2.46	3.100 (4)	123
C4—H4⋯N2iv	0.93	2.51	3.296 (4)	142
C7—H7C⋯O2v	0.96	2.57	3.445 (4)	152

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