2,3-Dimethyl-6-nitro-2H-indazole.

In the mol-ecule of the title compound, C(9)H(9)N(3)O(2), the indazole ring system is almost planar [maximum deviation = 0.019 (3) Å for the C atom bearing the nitro group]. In the crystal structure, inter-molecular C-H⋯O inter-actions link the mol-ecules into centrosymmetric dimers, forming R(2) (2)(18) ring motifs. Aromatic π-π contacts between indazole rings [centroid-centroid distances = 3.632 (1) and 3.705 (1) Å] may further stabilize the structure.

Related literature

For a related structure, see: Xu et al. (1999 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring-motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C9H9N3O2

M = 191.19

Triclinic,

a = 6.5800 (13) Å

b = 7.2050 (14) Å

c = 10.752 (2) Å

α = 75.07 (3)°

β = 74.67 (3)°

γ = 66.73 (3)°

V = 444.81 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 294 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.969, T max = 0.990

1756 measured reflections

1606 independent reflections

1292 reflections with I > 2σ(I)

R int = 0.031

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.154

S = 1.00

1606 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025410/hk2724sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025410/hk2724Isup2.hkl

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

C9H9N3O2	Z = 2
Mr = 191.19	F(000) = 200
Triclinic, P1	Dx = 1.427 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5800 (13) Å	Cell parameters from 25 reflections
b = 7.2050 (14) Å	θ = 9–13°
c = 10.752 (2) Å	µ = 0.11 mm−1
α = 75.07 (3)°	T = 294 K
β = 74.67 (3)°	Block, colorless
γ = 66.73 (3)°	0.30 × 0.20 × 0.10 mm
V = 444.81 (19) Å3

Enraf–Nonius CAD-4 diffractometer	1292 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = 0→7
Absorption correction: ψ scan (North et al., 1968)	k = −7→8
Tmin = 0.969, Tmax = 0.990	l = −12→12
1756 measured reflections	3 standard reflections every 120 min
1606 independent reflections	intensity decay: 1%

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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.08P)2 + 0.235P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1606 reflections	Δρmax = 0.32 e Å−3
129 parameters	Δρmin = −0.25 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: 0.059 (12)

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	0.2155 (5)	0.7495 (5)	−0.3831 (2)	0.1020 (9)
O2	−0.1339 (4)	0.7845 (4)	−0.33747 (19)	0.0803 (7)
N1	−0.2315 (3)	0.7731 (3)	0.25319 (18)	0.0469 (5)
N2	−0.3309 (3)	0.7997 (3)	0.15107 (18)	0.0479 (5)
N3	0.0392 (4)	0.7648 (3)	−0.3051 (2)	0.0611 (6)
C1	−0.3707 (5)	0.7880 (5)	0.3829 (2)	0.0660 (8)
H1A	−0.5144	0.8941	0.3758	0.099*
H1B	−0.2979	0.8202	0.4368	0.099*
H1C	−0.3915	0.6594	0.4218	0.099*
C2	0.1367 (5)	0.6977 (4)	0.3176 (3)	0.0601 (7)
H2B	0.0456	0.7087	0.4032	0.090*
H2C	0.2098	0.7971	0.2929	0.090*
H2D	0.2482	0.5625	0.3186	0.090*
C3	−0.0080 (4)	0.7362 (3)	0.2216 (2)	0.0432 (6)
C4	−0.1582 (3)	0.7777 (3)	0.0489 (2)	0.0390 (5)
C5	−0.1637 (4)	0.7888 (3)	−0.0830 (2)	0.0446 (6)
H5A	−0.2966	0.8160	−0.1108	0.054*
C6	0.0376 (4)	0.7573 (3)	−0.1678 (2)	0.0462 (6)
C7	0.2431 (4)	0.7224 (4)	−0.1315 (2)	0.0517 (6)
H7A	0.3741	0.7057	−0.1943	0.062*
C8	0.2482 (4)	0.7134 (3)	−0.0049 (2)	0.0470 (6)
H8A	0.3819	0.6910	0.0204	0.056*
C9	0.0474 (3)	0.7388 (3)	0.0874 (2)	0.0387 (5)

	U11	U22	U33	U12	U13	U23
O1	0.1021 (19)	0.150 (2)	0.0491 (12)	−0.0512 (17)	0.0174 (12)	−0.0311 (13)
O2	0.1002 (17)	0.0986 (16)	0.0521 (12)	−0.0371 (13)	−0.0217 (11)	−0.0183 (11)
N1	0.0480 (11)	0.0573 (12)	0.0389 (10)	−0.0226 (9)	−0.0063 (8)	−0.0089 (8)
N2	0.0436 (11)	0.0606 (12)	0.0427 (11)	−0.0218 (9)	−0.0069 (8)	−0.0098 (9)
N3	0.0804 (16)	0.0572 (13)	0.0453 (12)	−0.0255 (11)	−0.0051 (12)	−0.0129 (10)
C1	0.0621 (17)	0.095 (2)	0.0422 (14)	−0.0311 (15)	0.0000 (12)	−0.0173 (13)
C2	0.0642 (16)	0.0669 (17)	0.0564 (15)	−0.0235 (13)	−0.0231 (13)	−0.0092 (12)
C3	0.0475 (13)	0.0402 (12)	0.0459 (12)	−0.0177 (9)	−0.0112 (10)	−0.0077 (9)
C4	0.0400 (11)	0.0369 (11)	0.0427 (12)	−0.0162 (9)	−0.0058 (9)	−0.0085 (9)
C5	0.0501 (13)	0.0444 (12)	0.0442 (13)	−0.0207 (10)	−0.0117 (10)	−0.0061 (9)
C6	0.0611 (14)	0.0384 (12)	0.0389 (12)	−0.0202 (10)	−0.0034 (10)	−0.0079 (9)
C7	0.0465 (13)	0.0485 (13)	0.0523 (14)	−0.0148 (10)	0.0048 (10)	−0.0128 (11)
C8	0.0405 (12)	0.0423 (12)	0.0579 (14)	−0.0137 (9)	−0.0079 (10)	−0.0104 (10)
C9	0.0426 (12)	0.0306 (10)	0.0448 (12)	−0.0135 (8)	−0.0098 (9)	−0.0070 (8)

O1—N3	1.222 (3)	C2—H2C	0.9600
O2—N3	1.223 (3)	C2—H2D	0.9600
N1—N2	1.357 (3)	C3—C9	1.389 (3)
N1—C1	1.456 (3)	C4—C5	1.409 (3)
N1—C3	1.350 (3)	C4—C9	1.420 (3)
N2—C4	1.346 (3)	C5—C6	1.366 (3)
N3—C6	1.460 (3)	C5—H5A	0.9300
C1—H1A	0.9600	C6—C7	1.416 (4)
C1—H1B	0.9600	C7—C8	1.354 (3)
C1—H1C	0.9600	C7—H7A	0.9300
C2—C3	1.487 (3)	C8—C9	1.405 (3)
C2—H2B	0.9600	C8—H8A	0.9300
N2—N1—C1	118.6 (2)	N1—C3—C2	124.3 (2)
C3—N1—N2	114.84 (19)	C9—C3—C2	130.3 (2)
C3—N1—C1	126.6 (2)	N2—C4—C5	127.8 (2)
C4—N2—N1	102.99 (17)	N2—C4—C9	111.81 (19)
O1—N3—O2	122.6 (2)	C5—C4—C9	120.4 (2)
O1—N3—C6	118.2 (2)	C6—C5—C4	116.1 (2)
O2—N3—C6	119.2 (2)	C6—C5—H5A	121.9
N1—C1—H1A	109.5	C4—C5—H5A	121.9
N1—C1—H1B	109.5	C5—C6—C7	124.2 (2)
H1A—C1—H1B	109.5	C5—C6—N3	117.7 (2)
N1—C1—H1C	109.5	C7—C6—N3	118.1 (2)
H1A—C1—H1C	109.5	C8—C7—C6	119.7 (2)
H1B—C1—H1C	109.5	C8—C7—H7A	120.1
C3—C2—H2B	109.5	C6—C7—H7A	120.1
C3—C2—H2C	109.5	C7—C8—C9	118.6 (2)
H2B—C2—H2C	109.5	C7—C8—H8A	120.7
C3—C2—H2D	109.5	C9—C8—H8A	120.7
H2B—C2—H2D	109.5	C3—C9—C8	134.1 (2)
H2C—C2—H2D	109.5	C3—C9—C4	105.00 (19)
N1—C3—C9	105.36 (19)	C8—C9—C4	120.9 (2)
C1—N1—N2—C4	179.6 (2)	C2—C3—C9—C8	−2.1 (4)
C3—N1—N2—C4	0.1 (2)	N2—C4—C5—C6	−178.9 (2)
N2—N1—C3—C2	−178.6 (2)	C9—C4—C5—C6	0.9 (3)
N2—N1—C3—C9	0.2 (2)	N2—C4—C9—C3	0.4 (2)
C1—N1—C3—C2	1.9 (4)	N2—C4—C9—C8	−179.25 (18)
C1—N1—C3—C9	−179.3 (2)	C5—C4—C9—C3	−179.41 (19)
N1—N2—C4—C5	179.5 (2)	C5—C4—C9—C8	0.9 (3)
N1—N2—C4—C9	−0.3 (2)	C4—C5—C6—C7	−2.2 (3)
O1—N3—C6—C5	175.6 (2)	C4—C5—C6—N3	179.20 (19)
O1—N3—C6—C7	−3.1 (3)	C5—C6—C7—C8	1.8 (4)
O2—N3—C6—C5	−5.0 (3)	N3—C6—C7—C8	−179.7 (2)
O2—N3—C6—C7	176.4 (2)	C6—C7—C8—C9	0.2 (3)
N1—C3—C9—C4	−0.4 (2)	C7—C8—C9—C3	179.0 (2)
N1—C3—C9—C8	179.3 (2)	C7—C8—C9—C4	−1.4 (3)
C2—C3—C9—C4	178.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.96	2.58	3.533 (4)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.96	2.58	3.533 (4)	171

Symmetry code: (i) .