2-Methyl-6-nitro-2H-indazole.

In the title compound, C(8)H(7)N(3)O(2), the mol-ecular skeleton is almost planar with a maximum deviation of 0.0484 (9) Å for the methyl C atom. In the crystal, weak inter-molecular C-H⋯N and C-H⋯O hydrogen bonds help to establish the packing.

Related literature

For the synthesis, see: Sorbera et al. (2006 ▶); Balardi et al. (1997 ▶). For related structures, see: Qi et al. (2010 ▶); Chen et al. (2009 ▶). For applications of indazole derivatives, see, for example: Li et al. (2008 ▶).

Experimental

Crystal data

C8H7N3O2

M = 177.17

Monoclinic,

a = 3.793 (3) Å

b = 12.200 (8) Å

c = 16.675 (11) Å

β = 95.722 (9)°

V = 767.7 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 113 K

0.40 × 0.20 × 0.10 mm

Data collection

Rigaku Saturn724 CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.956, T max = 0.989

7726 measured reflections

1802 independent reflections

1317 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.092

S = 1.03

1802 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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: CrystalStructure (Rigaku/MSC, 2005 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019374/cv5096sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811019374/cv5096Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019374/cv5096Isup3.cdx

Supplementary material file. DOI: 10.1107/S1600536811019374/cv5096Isup4.cml

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

C8H7N3O2	F(000) = 368
Mr = 177.17	Dx = 1.533 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2636 reflections
a = 3.793 (3) Å	θ = 2.1–28.0°
b = 12.200 (8) Å	µ = 0.12 mm−1
c = 16.675 (11) Å	T = 113 K
β = 95.722 (9)°	Prism, colourless
V = 767.7 (9) Å3	0.40 × 0.20 × 0.10 mm
Z = 4

Rigaku Saturn724 CCD diffractometer	1802 independent reflections
Radiation source: rotating anode	1317 reflections with I > 2σ(I)
multilayer	Rint = 0.039
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω and φ scans	h = −4→4
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→16
Tmin = 0.956, Tmax = 0.989	l = −21→21
7726 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
1802 reflections	(Δ/σ)max = 0.001
119 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.23 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	0.0001 (2)	0.40192 (7)	1.13521 (6)	0.0330 (3)
O2	−0.1008 (2)	0.23042 (7)	1.15673 (5)	0.0285 (2)
N1	0.0034 (2)	0.30444 (8)	1.11496 (6)	0.0204 (2)
N2	0.2860 (2)	0.04933 (8)	0.90394 (6)	0.0191 (2)
N3	0.4265 (2)	0.07413 (8)	0.83460 (6)	0.0189 (2)
C1	0.2577 (3)	0.14834 (9)	0.93942 (7)	0.0164 (3)
C2	0.1284 (3)	0.16936 (9)	1.01433 (7)	0.0172 (3)
H2	0.0426	0.1128	1.0463	0.021*
C3	0.1351 (3)	0.27717 (9)	1.03783 (7)	0.0172 (3)
C4	0.2556 (3)	0.36516 (9)	0.99200 (7)	0.0197 (3)
H4	0.2521	0.4380	1.0120	0.024*
C5	0.3767 (3)	0.34458 (9)	0.91902 (7)	0.0202 (3)
H5	0.4565	0.4026	0.8874	0.024*
C6	0.3805 (3)	0.23462 (9)	0.89161 (7)	0.0175 (3)
C7	0.4868 (3)	0.18162 (9)	0.82402 (7)	0.0197 (3)
H7	0.5827	0.2147	0.7794	0.024*
C8	0.5084 (3)	−0.01456 (9)	0.78106 (8)	0.0225 (3)
H8A	0.6589	−0.0687	0.8114	0.034*
H8B	0.6335	0.0150	0.7372	0.034*
H8C	0.2879	−0.0497	0.7586	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0491 (6)	0.0212 (5)	0.0301 (5)	0.0001 (4)	0.0114 (4)	−0.0077 (4)
O2	0.0399 (5)	0.0249 (5)	0.0227 (5)	−0.0030 (4)	0.0126 (4)	0.0002 (4)
N1	0.0211 (5)	0.0207 (5)	0.0195 (5)	0.0007 (4)	0.0026 (4)	−0.0017 (4)
N2	0.0233 (5)	0.0198 (5)	0.0149 (5)	−0.0002 (4)	0.0058 (4)	0.0000 (4)
N3	0.0200 (5)	0.0216 (5)	0.0155 (5)	0.0003 (4)	0.0040 (4)	0.0004 (4)
C1	0.0147 (5)	0.0172 (5)	0.0171 (6)	0.0000 (4)	0.0004 (4)	0.0013 (4)
C2	0.0182 (6)	0.0172 (5)	0.0163 (6)	−0.0002 (4)	0.0021 (5)	0.0013 (4)
C3	0.0155 (6)	0.0203 (6)	0.0158 (6)	0.0016 (4)	0.0018 (5)	−0.0004 (5)
C4	0.0194 (6)	0.0161 (6)	0.0235 (6)	−0.0009 (4)	0.0010 (5)	0.0008 (5)
C5	0.0194 (6)	0.0189 (6)	0.0222 (6)	−0.0015 (5)	0.0026 (5)	0.0046 (5)
C6	0.0151 (6)	0.0208 (6)	0.0163 (6)	−0.0002 (4)	0.0008 (4)	0.0027 (5)
C7	0.0193 (6)	0.0218 (6)	0.0185 (6)	−0.0013 (5)	0.0036 (5)	0.0033 (5)
C8	0.0262 (6)	0.0234 (6)	0.0190 (6)	0.0016 (5)	0.0073 (5)	−0.0029 (5)

O1—N1	1.2367 (14)	C3—C4	1.4194 (17)
O2—N1	1.2294 (14)	C4—C5	1.3662 (19)
N1—C3	1.4639 (17)	C4—H4	0.9500
N2—C1	1.3539 (16)	C5—C6	1.4178 (17)
N2—N3	1.3547 (15)	C5—H5	0.9500
N3—C7	1.3459 (17)	C6—C7	1.3934 (18)
N3—C8	1.4559 (16)	C7—H7	0.9500
C1—C2	1.4102 (18)	C8—H8A	0.9800
C1—C6	1.4265 (17)	C8—H8B	0.9800
C2—C3	1.3719 (17)	C8—H8C	0.9800
C2—H2	0.9500
O2—N1—O1	122.63 (11)	C5—C4—H4	120.2
O2—N1—C3	119.20 (10)	C3—C4—H4	120.2
O1—N1—C3	118.17 (10)	C4—C5—C6	118.44 (11)
C1—N2—N3	103.23 (10)	C4—C5—H5	120.8
C7—N3—N2	114.58 (10)	C6—C5—H5	120.8
C7—N3—C8	126.47 (11)	C7—C6—C5	135.47 (11)
N2—N3—C8	118.91 (10)	C7—C6—C1	104.27 (11)
N2—C1—C2	126.80 (10)	C5—C6—C1	120.25 (11)
N2—C1—C6	111.69 (11)	N3—C7—C6	106.23 (11)
C2—C1—C6	121.50 (11)	N3—C7—H7	126.9
C3—C2—C1	115.41 (10)	C6—C7—H7	126.9
C3—C2—H2	122.3	N3—C8—H8A	109.5
C1—C2—H2	122.3	N3—C8—H8B	109.5
C2—C3—C4	124.70 (12)	H8A—C8—H8B	109.5
C2—C3—N1	118.07 (10)	N3—C8—H8C	109.5
C4—C3—N1	117.22 (10)	H8A—C8—H8C	109.5
C5—C4—C3	119.69 (11)	H8B—C8—H8C	109.5
C1—N2—N3—C7	−0.23 (12)	N1—C3—C4—C5	−179.08 (10)
C1—N2—N3—C8	177.69 (9)	C3—C4—C5—C6	−0.52 (16)
N3—N2—C1—C2	−179.34 (10)	C4—C5—C6—C7	−178.43 (12)
N3—N2—C1—C6	0.13 (12)	C4—C5—C6—C1	0.46 (16)
N2—C1—C2—C3	178.46 (10)	N2—C1—C6—C7	0.01 (12)
C6—C1—C2—C3	−0.96 (15)	C2—C1—C6—C7	179.51 (10)
C1—C2—C3—C4	0.92 (16)	N2—C1—C6—C5	−179.19 (9)
C1—C2—C3—N1	179.81 (9)	C2—C1—C6—C5	0.31 (16)
O2—N1—C3—C2	1.59 (15)	N2—N3—C7—C6	0.24 (12)
O1—N1—C3—C2	−178.04 (10)	C8—N3—C7—C6	−177.50 (10)
O2—N1—C3—C4	−179.44 (9)	C5—C6—C7—N3	178.87 (12)
O1—N1—C3—C4	0.93 (14)	C1—C6—C7—N3	−0.14 (11)
C2—C3—C4—C5	−0.19 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2i	0.95	2.52	3.446 (2)	164
C7—H7···O2ii	0.95	2.56	3.500 (2)	169
C8—H8A···O2iii	0.98	2.61	3.549 (2)	161
C8—H8B···O1ii	0.98	2.51	3.491 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N2i	0.95	2.52	3.446 (2)	164
C7—H7⋯O2ii	0.95	2.56	3.500 (2)	169
C8—H8A⋯O2iii	0.98	2.61	3.549 (2)	161
C8—H8B⋯O1ii	0.98	2.51	3.491 (2)	174

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