1-Allyl-6-nitro-1H-indazole.

The fused five- and six-membered rings in the title mol-ecule, C10H9N3O2, are essentially coplanar, the largest deviation from the mean plane being 0.012 (1) Å for the C atom linked to the nitro group. The fused-ring system makes a dihedral angle of 11.34 (6)° with the nitro group, leading to a syn-periplanar conformation. The plane through the atoms forming the allyl group is nearly perpendicular to the indazole fused-ring system, as indicated by the dihedral angle of 73.3 (5)°. In the crystal, each mol-ecule is linked to its symmetry equivalent about the center of inversion by pairs of non-classical C-H⋯O hydrogen bonds, forming an extended tape motif parallel to the (-12-1) plane.

Related literature

For the pharmacological and biochemical properties of substituted indazoles, see: Saczewski et al. (2008 ▶); Jones et al. (2009 ▶); Bouissane et al. (2006 ▶). For compounds with similar structures, see: El Brahmi et al. (2009 ▶, 2011 ▶).

Experimental

Crystal data

C10H9N3O2

M = 203.20

Triclinic,

a = 4.3630 (16) Å

b = 8.3245 (7) Å

c = 13.541 (5) Å

α = 95.647 (2)°

β = 98.46 (2)°

γ = 97.770 (2)°

V = 478.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.38 × 0.29 × 0.27 mm

Data collection

Bruker Kappa APEXII Quazar area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.957, T max = 0.997

8258 measured reflections

2109 independent reflections

1675 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.100

S = 1.06

2109 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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, 2012 ▶) and Mercury (Macrae et al. 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046478/pk2452sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046478/pk2452Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046478/pk2452Isup3.cml

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

C10H9N3O2	Z = 2
Mr = 203.20	F(000) = 212
Triclinic, P1	Dx = 1.410 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.3630 (16) Å	Cell parameters from 2109 reflections
b = 8.3245 (7) Å	θ = 3.7–27.1°
c = 13.541 (5) Å	µ = 0.10 mm−1
α = 95.647 (2)°	T = 296 K
β = 98.46 (2)°	Block, yellow
γ = 97.770 (2)°	0.38 × 0.29 × 0.27 mm
V = 478.5 (3) Å3

Bruker Kappa APEXII Quazar area-detector diffractometer	2109 independent reflections
Radiation source: microfocus sealed tube	1675 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.021
φ and ω scans	θmax = 27.1°, θmin = 3.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.957, Tmax = 0.997	k = −10→10
8258 measured reflections	l = −17→17

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)] = 0.034	Hydrogen site location: difference Fourier map
wR(F2) = 0.100	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0593P)2 + 0.0394P] where P = (Fo2 + 2Fc2)/3
2109 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.20 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 > 2σ(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
C1	0.5250 (3)	0.28071 (13)	0.07294 (8)	0.0285 (3)
C2	0.7333 (3)	0.42576 (14)	0.10756 (9)	0.0336 (3)
H2	0.8493	0.4767	0.0639	0.040*
C3	0.7649 (3)	0.49196 (14)	0.20582 (9)	0.0347 (3)
H3	0.9001	0.5887	0.2297	0.042*
C4	0.5890 (3)	0.41073 (13)	0.26971 (9)	0.0296 (3)
C5	0.3813 (3)	0.26597 (13)	0.23161 (8)	0.0269 (3)
C6	0.3433 (3)	0.19722 (13)	0.13128 (8)	0.0279 (3)
H6	0.2053	0.1020	0.1061	0.034*
C7	0.5573 (3)	0.43449 (15)	0.37259 (9)	0.0357 (3)
H7	0.6669	0.5214	0.4182	0.043*
C8	0.0238 (3)	0.06785 (15)	0.31003 (9)	0.0337 (3)
H8A	−0.1083	0.0416	0.2447	0.040*
H8B	−0.1104	0.0882	0.3595	0.040*
C9	0.1822 (3)	−0.07536 (15)	0.33350 (11)	0.0430 (3)
H9	0.3288	−0.1040	0.2942	0.052*
C10	0.1274 (4)	−0.16305 (18)	0.40592 (12)	0.0599 (4)
H10A	0.2369	−0.2555	0.4167	0.072*
H10B	−0.0296	−0.1344	0.4488	0.072*
N1	0.5029 (2)	0.21201 (12)	−0.03272 (7)	0.0335 (3)
N2	0.2434 (2)	0.21521 (11)	0.30948 (7)	0.0306 (2)
N3	0.3528 (3)	0.31791 (12)	0.39570 (7)	0.0360 (3)
O1	0.2915 (2)	0.09935 (12)	−0.06728 (7)	0.0468 (3)
O2	0.6971 (3)	0.26879 (12)	−0.08121 (7)	0.0515 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0332 (6)	0.0299 (5)	0.0236 (6)	0.0101 (5)	0.0050 (5)	0.0012 (4)
C2	0.0385 (7)	0.0296 (6)	0.0340 (6)	0.0042 (5)	0.0099 (5)	0.0051 (5)
C3	0.0399 (7)	0.0263 (5)	0.0361 (7)	0.0005 (5)	0.0068 (5)	0.0003 (5)
C4	0.0342 (6)	0.0265 (5)	0.0271 (6)	0.0064 (5)	0.0028 (5)	−0.0015 (4)
C5	0.0279 (5)	0.0280 (5)	0.0255 (6)	0.0073 (4)	0.0036 (4)	0.0031 (4)
C6	0.0290 (6)	0.0276 (5)	0.0257 (6)	0.0046 (4)	0.0018 (4)	−0.0008 (4)
C7	0.0429 (7)	0.0339 (6)	0.0266 (6)	0.0020 (5)	0.0029 (5)	−0.0044 (5)
C8	0.0300 (6)	0.0421 (6)	0.0261 (6)	−0.0028 (5)	0.0041 (5)	0.0023 (5)
C9	0.0370 (7)	0.0356 (7)	0.0521 (8)	−0.0037 (5)	0.0074 (6)	−0.0032 (6)
C10	0.0817 (12)	0.0388 (7)	0.0518 (9)	0.0053 (8)	−0.0079 (8)	0.0024 (7)
N1	0.0409 (6)	0.0351 (5)	0.0263 (5)	0.0117 (4)	0.0070 (4)	0.0021 (4)
N2	0.0343 (5)	0.0336 (5)	0.0223 (5)	0.0018 (4)	0.0048 (4)	0.0005 (4)
N3	0.0426 (6)	0.0387 (6)	0.0240 (5)	0.0034 (5)	0.0036 (4)	−0.0031 (4)
O1	0.0512 (6)	0.0529 (6)	0.0297 (5)	−0.0007 (5)	0.0020 (4)	−0.0088 (4)
O2	0.0659 (7)	0.0549 (6)	0.0364 (5)	0.0031 (5)	0.0255 (5)	0.0017 (4)

C1—C6	1.3706 (16)	C7—H7	0.9300
C1—C2	1.4036 (17)	C8—N2	1.4522 (15)
C1—N1	1.4720 (15)	C8—C9	1.4942 (18)
C2—C3	1.3691 (17)	C8—H8A	0.9700
C2—H2	0.9300	C8—H8B	0.9700
C3—C4	1.4016 (16)	C9—C10	1.309 (2)
C3—H3	0.9300	C9—H9	0.9300
C4—C5	1.4087 (15)	C10—H10A	0.9711
C4—C7	1.4174 (17)	C10—H10B	0.9983
C5—N2	1.3631 (14)	N1—O2	1.2203 (13)
C5—C6	1.3985 (16)	N1—O1	1.2256 (14)
C6—H6	0.9300	N2—N3	1.3605 (14)
C7—N3	1.3204 (16)
C6—C1—C2	124.41 (11)	C4—C7—H7	124.2
C6—C1—N1	117.64 (10)	N2—C8—C9	112.95 (10)
C2—C1—N1	117.95 (10)	N2—C8—H8A	109.0
C3—C2—C1	119.75 (11)	C9—C8—H8A	109.0
C3—C2—H2	120.1	N2—C8—H8B	109.0
C1—C2—H2	120.1	C9—C8—H8B	109.0
C2—C3—C4	118.53 (11)	H8A—C8—H8B	107.8
C2—C3—H3	120.7	C10—C9—C8	124.06 (14)
C4—C3—H3	120.7	C10—C9—H9	118.0
C3—C4—C5	119.81 (11)	C8—C9—H9	118.0
C3—C4—C7	136.30 (11)	C9—C10—H10A	119.9
C5—C4—C7	103.89 (10)	C9—C10—H10B	119.2
N2—C5—C6	130.53 (10)	H10A—C10—H10B	120.9
N2—C5—C4	106.94 (10)	O2—N1—O1	123.28 (10)
C6—C5—C4	122.53 (10)	O2—N1—C1	118.53 (10)
C1—C6—C5	114.96 (10)	O1—N1—C1	118.18 (10)
C1—C6—H6	122.5	N3—N2—C5	111.12 (10)
C5—C6—H6	122.5	N3—N2—C8	120.52 (9)
N3—C7—C4	111.61 (11)	C5—N2—C8	128.23 (9)
N3—C7—H7	124.2	C7—N3—N2	106.44 (10)
C6—C1—C2—C3	0.27 (18)	N2—C8—C9—C10	125.37 (14)
N1—C1—C2—C3	−178.80 (10)	C6—C1—N1—O2	−168.29 (10)
C1—C2—C3—C4	0.77 (17)	C2—C1—N1—O2	10.84 (16)
C2—C3—C4—C5	−1.17 (16)	C6—C1—N1—O1	11.05 (16)
C2—C3—C4—C7	178.55 (13)	C2—C1—N1—O1	−169.83 (10)
C3—C4—C5—N2	−179.75 (10)	C6—C5—N2—N3	178.95 (11)
C7—C4—C5—N2	0.45 (12)	C4—C5—N2—N3	−0.67 (12)
C3—C4—C5—C6	0.59 (16)	C6—C5—N2—C8	3.07 (19)
C7—C4—C5—C6	−179.21 (10)	C4—C5—N2—C8	−176.55 (11)
C2—C1—C6—C5	−0.84 (16)	C9—C8—N2—N3	−88.19 (13)
N1—C1—C6—C5	178.23 (9)	C9—C8—N2—C5	87.34 (14)
N2—C5—C6—C1	−179.17 (10)	C4—C7—N3—N2	−0.31 (14)
C4—C5—C6—C1	0.40 (15)	C5—N2—N3—C7	0.62 (13)
C3—C4—C7—N3	−179.84 (13)	C8—N2—N3—C7	176.85 (10)
C5—C4—C7—N3	−0.09 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1i	0.93	2.51	3.3973 (17)	160
C8—H8A···O1i	0.97	2.53	3.4475 (19)	157
C2—H2···O2ii	0.93	2.66	3.3911 (17)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1i	0.93	2.51	3.3973 (17)	160
C8—H8A⋯O1i	0.97	2.53	3.4475 (19)	157
C2—H2⋯O2ii	0.93	2.66	3.3911 (17)	136

Symmetry codes: (i) ; (ii) .