5-(2-Methyl-5-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 45.7 (2)° with the tetra-zole ring. In the crystal structure, the mol-ecules are linked into a chain running along the a axis by N-H⋯N hydrogen bonds, and the chains are linked through π-π inter-actions between the tetra-zole rings [centroid-centroid distance = 3.450 (2) Å].

Related literature

For the use of tetra­zole derivatives in coordination chemisty, see: Arp et al. (2000 ▶); Dai & Fu (2008 ▶); Wang et al. (2005 ▶); Xiong et al. (2002 ▶).

Experimental

Crystal data

C8H7N5O2

M = 205.19

Monoclinic,

a = 4.9057 (10) Å

b = 16.938 (3) Å

c = 11.463 (2) Å

β = 98.65 (3)°

V = 941.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 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

9281 measured reflections

2085 independent reflections

1434 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.082

wR(F 2) = 0.203

S = 1.13

2085 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.29 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 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536808029176/ci2669sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029176/ci2669Isup2.hkl

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

C8H7N5O2	F(000) = 424
Mr = 205.19	Dx = 1.447 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1775 reflections
a = 4.9057 (10) Å	θ = 2.4–27.1°
b = 16.938 (3) Å	µ = 0.11 mm−1
c = 11.463 (2) Å	T = 298 K
β = 98.65 (3)°	Block, colourless
V = 941.7 (3) Å3	0.25 × 0.18 × 0.15 mm
Z = 4

Rigaku Mercury2 diffractometer	2085 independent reflections
Radiation source: fine-focus sealed tube	1434 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 13.6612 pixels mm-1	θmax = 27.2°, θmin = 3.0°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005)	k = −21→21
Tmin = 0.971, Tmax = 0.977	l = −14→14
9281 measured reflections

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)] = 0.082	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.203	H-atom parameters constrained
S = 1.13	w = 1/[σ2(Fo2) + (0.0655P)2 + 0.9796P] where P = (Fo2 + 2Fc2)/3
2085 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.29 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
O1	−0.0317 (10)	0.86679 (19)	0.3611 (3)	0.1152 (15)
O2	−0.2052 (8)	0.7689 (2)	0.4436 (3)	0.0930 (12)
N1	0.5142 (5)	0.48416 (16)	0.3549 (2)	0.0425 (7)
H1	0.6766	0.4970	0.3419	0.051*
N4	0.0825 (5)	0.48791 (16)	0.3638 (2)	0.0416 (7)
N3	0.1836 (6)	0.41763 (16)	0.4075 (3)	0.0473 (7)
C1	0.2904 (6)	0.52855 (17)	0.3320 (3)	0.0360 (7)
N2	0.4451 (6)	0.41548 (16)	0.4018 (3)	0.0470 (7)
C2	0.2681 (6)	0.61097 (19)	0.2897 (3)	0.0397 (7)
C7	0.3890 (7)	0.6358 (2)	0.1932 (3)	0.0485 (9)
C3	0.1193 (7)	0.6641 (2)	0.3495 (3)	0.0426 (8)
H3	0.0349	0.6473	0.4125	0.051*
C4	0.1007 (7)	0.7403 (2)	0.3140 (3)	0.0506 (9)
C6	0.3672 (8)	0.7152 (2)	0.1624 (3)	0.0565 (10)
H6	0.4510	0.7333	0.0999	0.068*
N5	−0.0555 (8)	0.7961 (2)	0.3775 (3)	0.0676 (10)
C5	0.2254 (9)	0.7676 (2)	0.2220 (4)	0.0628 (11)
H5	0.2136	0.8206	0.2006	0.075*
C8	0.5334 (9)	0.5794 (2)	0.1215 (4)	0.0628 (11)
H8A	0.4164	0.5347	0.0992	0.094*
H8B	0.7020	0.5618	0.1677	0.094*
H8C	0.5738	0.6056	0.0519	0.094*

	U11	U22	U33	U12	U13	U23
O1	0.197 (4)	0.0494 (19)	0.105 (3)	0.033 (2)	0.042 (3)	0.0013 (19)
O2	0.107 (3)	0.089 (2)	0.095 (3)	0.032 (2)	0.054 (2)	0.003 (2)
N1	0.0275 (13)	0.0435 (15)	0.0576 (18)	0.0007 (12)	0.0105 (12)	0.0030 (13)
N4	0.0317 (13)	0.0391 (14)	0.0558 (17)	−0.0045 (11)	0.0129 (12)	0.0006 (13)
N3	0.0422 (16)	0.0397 (15)	0.0616 (19)	−0.0060 (13)	0.0132 (14)	0.0008 (14)
C1	0.0293 (15)	0.0369 (16)	0.0428 (17)	−0.0034 (13)	0.0090 (13)	0.0002 (14)
N2	0.0434 (16)	0.0359 (14)	0.0637 (19)	0.0033 (12)	0.0144 (14)	0.0005 (13)
C2	0.0305 (15)	0.0437 (17)	0.0455 (18)	−0.0033 (13)	0.0076 (13)	0.0006 (15)
C7	0.0400 (18)	0.061 (2)	0.0447 (19)	0.0012 (16)	0.0085 (15)	0.0040 (17)
C3	0.0394 (17)	0.0451 (18)	0.0443 (19)	0.0003 (14)	0.0096 (14)	0.0048 (15)
C4	0.051 (2)	0.049 (2)	0.052 (2)	0.0093 (16)	0.0103 (17)	0.0000 (17)
C6	0.061 (2)	0.055 (2)	0.057 (2)	0.0009 (19)	0.0216 (19)	0.0211 (19)
N5	0.086 (3)	0.055 (2)	0.062 (2)	0.0235 (19)	0.013 (2)	0.0028 (18)
C5	0.070 (3)	0.050 (2)	0.071 (3)	0.008 (2)	0.019 (2)	0.016 (2)
C8	0.067 (3)	0.072 (3)	0.056 (2)	0.012 (2)	0.029 (2)	0.000 (2)

O1—N5	1.220 (5)	C7—C8	1.505 (5)
O2—N5	1.222 (5)	C3—C4	1.352 (5)
N1—C1	1.324 (4)	C3—H3	0.93
N1—N2	1.346 (4)	C4—C5	1.377 (5)
N1—H1	0.86	C4—N5	1.477 (5)
N4—C1	1.326 (4)	C6—C5	1.371 (5)
N4—N3	1.357 (4)	C6—H6	0.93
N3—N2	1.294 (4)	C5—H5	0.93
C1—C2	1.477 (4)	C8—H8A	0.96
C2—C7	1.396 (5)	C8—H8B	0.96
C2—C3	1.401 (4)	C8—H8C	0.96
C7—C6	1.391 (5)
C1—N1—N2	108.6 (2)	C3—C4—C5	122.2 (3)
C1—N1—H1	125.7	C3—C4—N5	118.7 (3)
N2—N1—H1	125.7	C5—C4—N5	119.1 (3)
C1—N4—N3	107.7 (2)	C5—C6—C7	121.7 (3)
N2—N3—N4	108.4 (2)	C5—C6—H6	119.2
N1—C1—N4	107.5 (3)	C7—C6—H6	119.2
N1—C1—C2	128.3 (3)	O1—N5—O2	123.2 (4)
N4—C1—C2	124.0 (3)	O1—N5—C4	118.9 (4)
N3—N2—N1	107.9 (3)	O2—N5—C4	117.9 (3)
C7—C2—C3	120.6 (3)	C6—C5—C4	118.8 (4)
C7—C2—C1	121.7 (3)	C6—C5—H5	120.6
C3—C2—C1	117.7 (3)	C4—C5—H5	120.6
C6—C7—C2	117.8 (3)	C7—C8—H8A	109.5
C6—C7—C8	120.0 (3)	C7—C8—H8B	109.5
C2—C7—C8	122.2 (3)	H8A—C8—H8B	109.5
C4—C3—C2	118.9 (3)	C7—C8—H8C	109.5
C4—C3—H3	120.6	H8A—C8—H8C	109.5
C2—C3—H3	120.6	H8B—C8—H8C	109.5
C1—N4—N3—N2	−0.4 (4)	C1—C2—C7—C8	4.1 (5)
N2—N1—C1—N4	−0.3 (4)	C7—C2—C3—C4	−1.6 (5)
N2—N1—C1—C2	174.4 (3)	C1—C2—C3—C4	178.6 (3)
N3—N4—C1—N1	0.4 (4)	C2—C3—C4—C5	−0.7 (6)
N3—N4—C1—C2	−174.5 (3)	C2—C3—C4—N5	−179.8 (3)
N4—N3—N2—N1	0.2 (4)	C2—C7—C6—C5	−1.9 (6)
C1—N1—N2—N3	0.1 (4)	C8—C7—C6—C5	176.7 (4)
N1—C1—C2—C7	49.1 (5)	C3—C4—N5—O1	166.6 (4)
N4—C1—C2—C7	−137.0 (3)	C5—C4—N5—O1	−12.5 (6)
N1—C1—C2—C3	−131.2 (3)	C3—C4—N5—O2	−14.0 (6)
N4—C1—C2—C3	42.7 (5)	C5—C4—N5—O2	166.9 (4)
C3—C2—C7—C6	2.9 (5)	C7—C6—C5—C4	−0.4 (6)
C1—C2—C7—C6	−177.4 (3)	C3—C4—C5—C6	1.7 (6)
C3—C2—C7—C8	−175.7 (3)	N5—C4—C5—C6	−179.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.86	1.98	2.775 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.86	1.98	2.775 (4)	154

Symmetry code: (i) .