5-(4-Methyl-3-nitro-phen-yl)-1H-tetra-zole.

In the title compound, C(8)H(7)N(5)O(2), the benzene ring makes a dihedral angle of 38.27 (11)° with the tetra-zole ring. The crystal structure is stabilized by N-H⋯N hydrogen bonds, forming an infinite one-dimensional chain parallel to the a axis.

Related literature

For the use of tetra­zole derivatives in coordination chemisty, see: Arp et al. (2000 ▶); Hu et al. (2007 ▶); Wang et al. (2005 ▶); Xiong et al. (2002 ▶).

Experimental

Crystal data

C8H7N5O2

M = 205.19

Monoclinic,

a = 4.9642 (10) Å

b = 16.982 (3) Å

c = 10.804 (2) Å

β = 100.71 (3)°

V = 894.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 298 (2) K

0.25 × 0.18 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.971, T max = 0.977

7013 measured reflections

2039 independent reflections

1330 reflections with I > 2σ(I)

R int = 0.093

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.190

S = 1.08

2039 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018825/dn2361sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018825/dn2361Isup2.hkl

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

C8H7N5O2	F(000) = 424
Mr = 205.19	Dx = 1.523 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2043 reflections
a = 4.9642 (10) Å	θ = 3.1–27.5°
b = 16.982 (3) Å	µ = 0.12 mm−1
c = 10.804 (2) Å	T = 298 K
β = 100.71 (3)°	Block, colorless
V = 894.9 (3) Å3	0.25 × 0.18 × 0.15 mm
Z = 4

Rigaku Mercury2 diffractometer	2039 independent reflections
Radiation source: fine-focus sealed tube	1330 reflections with I > 2σ(I)
graphite	Rint = 0.093
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −22→21
Tmin = 0.971, Tmax = 0.977	l = −13→14
7013 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)] = 0.075	H-atom parameters constrained
wR(F2) = 0.190	w = 1/[σ2(Fo2) + (0.0844P)2 + 0.0553P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2039 reflections	Δρmax = 0.32 e Å−3
137 parameters	Δρmin = −0.26 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: 0.037 (7)

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	0.0809 (4)	0.47072 (13)	0.8636 (2)	0.0355 (6)
H1A	−0.0824	0.4579	0.8719	0.043*
N4	0.5077 (4)	0.46190 (13)	0.8535 (2)	0.0375 (6)
C1	0.2914 (5)	0.42106 (15)	0.8715 (2)	0.0300 (6)
C2	0.2791 (5)	0.33663 (15)	0.8959 (2)	0.0316 (6)
N2	0.1626 (5)	0.54380 (12)	0.8406 (2)	0.0429 (6)
N3	0.4204 (5)	0.53814 (13)	0.8340 (2)	0.0445 (6)
C3	0.1202 (5)	0.30784 (15)	0.9784 (2)	0.0346 (6)
H3A	0.0240	0.3423	1.0211	0.041*
C4	0.1057 (5)	0.22713 (16)	0.9969 (2)	0.0360 (7)
C7	0.4202 (6)	0.28333 (16)	0.8331 (3)	0.0380 (6)
H7A	0.5288	0.3016	0.7777	0.046*
C6	0.3991 (6)	0.20365 (16)	0.8530 (3)	0.0448 (7)
H6A	0.4927	0.1694	0.8089	0.054*
C5	0.2449 (6)	0.17202 (15)	0.9358 (3)	0.0423 (7)
O1	−0.1907 (5)	0.25440 (14)	1.1326 (2)	0.0687 (8)
O2	−0.0896 (5)	0.13387 (15)	1.1108 (2)	0.0781 (9)
N5	−0.0701 (5)	0.20355 (16)	1.0866 (2)	0.0468 (7)
C8	0.2416 (8)	0.08409 (18)	0.9527 (4)	0.0681 (10)
H8A	0.3551	0.0599	0.9006	0.102*
H8B	0.0571	0.0650	0.9289	0.102*
H8C	0.3103	0.0713	1.0393	0.102*

	U11	U22	U33	U12	U13	U23
N1	0.0248 (12)	0.0353 (12)	0.0489 (14)	−0.0016 (9)	0.0130 (9)	0.0005 (9)
N4	0.0280 (12)	0.0381 (13)	0.0489 (15)	−0.0015 (9)	0.0138 (9)	0.0055 (10)
C1	0.0237 (13)	0.0375 (14)	0.0308 (13)	−0.0009 (10)	0.0101 (9)	−0.0005 (10)
C2	0.0231 (13)	0.0376 (14)	0.0350 (15)	0.0014 (10)	0.0076 (10)	−0.0001 (10)
N2	0.0352 (13)	0.0384 (14)	0.0569 (16)	−0.0006 (10)	0.0135 (11)	0.0049 (11)
N3	0.0366 (14)	0.0415 (14)	0.0587 (16)	−0.0041 (10)	0.0172 (11)	0.0038 (11)
C3	0.0295 (15)	0.0390 (15)	0.0374 (16)	0.0000 (11)	0.0120 (11)	−0.0006 (11)
C4	0.0320 (15)	0.0399 (15)	0.0363 (15)	−0.0035 (11)	0.0065 (11)	0.0057 (11)
C7	0.0349 (15)	0.0411 (15)	0.0406 (16)	0.0059 (11)	0.0141 (12)	−0.0002 (12)
C6	0.0464 (18)	0.0422 (17)	0.0466 (18)	0.0123 (13)	0.0106 (13)	−0.0044 (12)
C5	0.0426 (17)	0.0371 (16)	0.0442 (17)	0.0017 (12)	0.0005 (13)	0.0024 (12)
O1	0.0701 (17)	0.0762 (17)	0.0721 (17)	−0.0033 (13)	0.0451 (13)	0.0098 (13)
O2	0.096 (2)	0.0572 (16)	0.087 (2)	−0.0154 (12)	0.0304 (16)	0.0263 (13)
N5	0.0377 (15)	0.0574 (17)	0.0444 (15)	−0.0108 (11)	0.0053 (11)	0.0132 (12)
C8	0.091 (3)	0.0377 (18)	0.074 (3)	−0.0006 (17)	0.011 (2)	0.0031 (16)

N1—C1	1.333 (3)	C4—N5	1.475 (3)
N1—N2	1.343 (3)	C7—C6	1.377 (4)
N1—H1A	0.8600	C7—H7A	0.9300
N4—C1	1.323 (3)	C6—C5	1.388 (4)
N4—N3	1.369 (3)	C6—H6A	0.9300
C1—C2	1.461 (3)	C5—C8	1.505 (4)
C2—C3	1.385 (3)	O1—N5	1.209 (3)
C2—C7	1.395 (3)	O2—N5	1.220 (3)
N2—N3	1.299 (3)	C8—H8A	0.9600
C3—C4	1.389 (4)	C8—H8B	0.9600
C3—H3A	0.9300	C8—H8C	0.9600
C4—C5	1.400 (4)
C1—N1—N2	109.7 (2)	C6—C7—C2	120.1 (2)
C1—N1—H1A	125.2	C6—C7—H7A	119.9
N2—N1—H1A	125.2	C2—C7—H7A	119.9
C1—N4—N3	106.0 (2)	C7—C6—C5	123.2 (3)
N4—C1—N1	107.9 (2)	C7—C6—H6A	118.4
N4—C1—C2	127.1 (2)	C5—C6—H6A	118.4
N1—C1—C2	125.0 (2)	C6—C5—C4	115.1 (2)
C3—C2—C7	118.8 (2)	C6—C5—C8	118.8 (3)
C3—C2—C1	120.7 (2)	C4—C5—C8	126.0 (3)
C7—C2—C1	120.5 (2)	O1—N5—O2	122.7 (3)
N3—N2—N1	106.0 (2)	O1—N5—C4	118.4 (2)
N2—N3—N4	110.4 (2)	O2—N5—C4	119.0 (3)
C2—C3—C4	119.5 (2)	C5—C8—H8A	109.5
C2—C3—H3A	120.3	C5—C8—H8B	109.5
C4—C3—H3A	120.3	H8A—C8—H8B	109.5
C5—C4—C3	123.3 (2)	C5—C8—H8C	109.5
C5—C4—N5	122.2 (3)	H8A—C8—H8C	109.5
C3—C4—N5	114.5 (2)	H8B—C8—H8C	109.5
N3—N4—C1—N1	−0.1 (3)	C2—C3—C4—N5	−179.9 (2)
N3—N4—C1—C2	179.8 (2)	C3—C2—C7—C6	0.4 (4)
N2—N1—C1—N4	−0.2 (3)	C1—C2—C7—C6	−177.5 (2)
N2—N1—C1—C2	179.9 (2)	C2—C7—C6—C5	−1.1 (4)
N4—C1—C2—C3	142.9 (3)	C7—C6—C5—C4	1.2 (4)
N1—C1—C2—C3	−37.2 (4)	C7—C6—C5—C8	−178.5 (3)
N4—C1—C2—C7	−39.2 (4)	C3—C4—C5—C6	−0.6 (4)
N1—C1—C2—C7	140.7 (3)	N5—C4—C5—C6	179.2 (2)
C1—N1—N2—N3	0.4 (3)	C3—C4—C5—C8	179.1 (3)
N1—N2—N3—N4	−0.5 (3)	N5—C4—C5—C8	−1.1 (4)
C1—N4—N3—N2	0.4 (3)	C5—C4—N5—O1	−177.7 (3)
C7—C2—C3—C4	0.1 (4)	C3—C4—N5—O1	2.2 (4)
C1—C2—C3—C4	178.1 (2)	C5—C4—N5—O2	1.9 (4)
C2—C3—C4—C5	0.0 (4)	C3—C4—N5—O2	−178.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4i	0.86	2.01	2.832 (3)	160.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N4i	0.86	2.01	2.832 (3)	160

Symmetry code: (i) .