2-Allyl-7-nitro-2H-indazole.

The asymmetric unit of the title compound, C10H9N3O2, contains two independent mol-ecules linked by a C-H⋯N hydrogen bond. Each mol-ecule has a similar conformation, being built up from fused five- and six-membered rings, each linked to an ally and nitro group, respectively. The indazole ring system makes dihedral angles of 2.7 (2) and 2.2 (2)°, respectively, with the plane through the nitro group. The allyl group is nearly perpendicular to the indazole system, as indicated by the N-N-C-C torsion angles of -75.3 (2) and -82.2 (2)°, this being the most important difference between the conformations of the two mol-ecules. In the crystal, mol-ecules are linked by C-H⋯O and π-π [inter-centroid distance = 3.6225 (8) Å] inter-actions to form a three-dimensional network.

Related literature

For pharmacological effects of indazole derivatives, see: Baraldi et al. (2001 ▶); Li et al. (2003 ▶); Lee et al. (2001 ▶); Rodgers et al. (1996 ▶); Schmidt et al. (2008 ▶). For similar compounds, see: El Brahmi et al. (2012 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C10H9N3O2

M = 203.20

Triclinic,

a = 8.1848 (3) Å

b = 8.3253 (4) Å

c = 16.3194 (6) Å

α = 84.168 (2)°

β = 85.653 (2)°

γ = 60.843 (2)°

V = 965.64 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.42 × 0.29 × 0.17 mm

Data collection

Bruker X8 APEX diffractometer

22310 measured reflections

4980 independent reflections

4107 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.142

S = 1.04

4980 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.24 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813026743/tk5258sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026743/tk5258Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813026743/tk5258Isup3.cml

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

C10H9N3O2	Z = 4
Mr = 203.20	F(000) = 424
Triclinic, P1	Dx = 1.398 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1848 (3) Å	Cell parameters from 4980 reflections
b = 8.3253 (4) Å	θ = 2.5–28.7°
c = 16.3194 (6) Å	µ = 0.10 mm−1
α = 84.168 (2)°	T = 296 K
β = 85.653 (2)°	Irregular shape, colourless
γ = 60.843 (2)°	0.42 × 0.29 × 0.17 mm
V = 965.64 (7) Å3

Bruker X8 APEX diffractometer	4107 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 28.7°, θmin = 2.5°
φ and ω scans	h = −11→11
22310 measured reflections	k = −11→11
4980 independent reflections	l = −22→22

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.076P)2 + 0.1973P] where P = (Fo2 + 2Fc2)/3
4980 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.24 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	0.40636 (16)	0.52858 (16)	0.63233 (7)	0.0352 (2)
C2	0.32039 (17)	0.46916 (16)	0.57894 (7)	0.0365 (3)
C3	0.22059 (19)	0.58263 (18)	0.51389 (8)	0.0439 (3)
H3	0.1656	0.5413	0.4795	0.053*
C4	0.1994 (2)	0.76114 (19)	0.49786 (9)	0.0506 (3)
H4	0.1297	0.8363	0.4534	0.061*
C5	0.2794 (2)	0.82492 (18)	0.54647 (9)	0.0491 (3)
H5	0.2659	0.9425	0.5354	0.059*
C6	0.38287 (18)	0.71050 (17)	0.61358 (8)	0.0406 (3)
C7	0.4834 (2)	0.7291 (2)	0.67340 (9)	0.0478 (3)
H7	0.4978	0.8314	0.6792	0.057*
C8	0.6739 (2)	0.5268 (3)	0.79150 (9)	0.0568 (4)
H8A	0.6289	0.4718	0.8366	0.068*
H8B	0.6606	0.6404	0.8092	0.068*
C9	0.8763 (2)	0.3989 (3)	0.77569 (10)	0.0595 (4)
H9	0.9568	0.3830	0.8168	0.071*
C10	0.9523 (3)	0.3085 (3)	0.71208 (12)	0.0699 (5)
H10A	0.8786	0.3191	0.6690	0.084*
H10B	1.0812	0.2321	0.7089	0.084*
N1	0.51163 (16)	0.44398 (16)	0.69883 (7)	0.0424 (3)
N2	0.55488 (16)	0.57195 (17)	0.72082 (7)	0.0463 (3)
N3	0.33824 (17)	0.28617 (16)	0.59100 (8)	0.0469 (3)
O1	0.2663 (3)	0.24031 (19)	0.54180 (9)	0.0862 (5)
O2	0.42204 (19)	0.18615 (16)	0.65005 (8)	0.0689 (3)
C11	0.77659 (16)	0.77408 (16)	0.98570 (7)	0.0358 (3)
C12	0.71532 (16)	0.68123 (16)	1.04771 (7)	0.0357 (3)
C13	0.64456 (19)	0.75454 (19)	1.12190 (8)	0.0444 (3)
H13	0.6060	0.6915	1.1621	0.053*
C14	0.6294 (2)	0.9241 (2)	1.13810 (10)	0.0543 (4)
H14	0.5804	0.9718	1.1888	0.065*
C15	0.6852 (2)	1.0194 (2)	1.08103 (10)	0.0541 (4)
H15	0.6741	1.1317	1.0922	0.065*
C16	0.75989 (19)	0.94553 (17)	1.00491 (9)	0.0437 (3)
C17	0.8334 (2)	1.0005 (2)	0.93490 (10)	0.0543 (4)
H17	0.8441	1.1072	0.9265	0.065*
C18	0.9745 (2)	0.8661 (3)	0.80039 (10)	0.0671 (5)
H18A	1.0708	0.7405	0.7924	0.081*
H18B	1.0348	0.9421	0.7980	0.081*
C19	0.8404 (2)	0.9320 (2)	0.73243 (10)	0.0573 (4)
H19	0.7356	1.0480	0.7344	0.069*
C20	0.8612 (3)	0.8364 (3)	0.67013 (12)	0.0725 (5)
H20A	0.9647	0.7199	0.6665	0.087*
H20B	0.7726	0.8848	0.6294	0.087*
N4	0.85309 (16)	0.72904 (16)	0.90988 (7)	0.0434 (3)
N5	0.88521 (17)	0.87130 (18)	0.88237 (8)	0.0505 (3)
N6	0.72571 (15)	0.50676 (15)	1.03441 (7)	0.0415 (2)
O3	0.78980 (18)	0.43963 (15)	0.96842 (7)	0.0602 (3)
O4	0.67488 (19)	0.43012 (16)	1.09090 (8)	0.0691 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0349 (5)	0.0344 (5)	0.0368 (6)	−0.0177 (5)	0.0018 (4)	−0.0023 (4)
C2	0.0381 (6)	0.0340 (5)	0.0391 (6)	−0.0191 (5)	0.0006 (5)	−0.0028 (5)
C3	0.0472 (7)	0.0438 (7)	0.0408 (6)	−0.0213 (6)	−0.0050 (5)	−0.0044 (5)
C4	0.0571 (8)	0.0405 (7)	0.0450 (7)	−0.0172 (6)	−0.0076 (6)	0.0049 (5)
C5	0.0575 (8)	0.0323 (6)	0.0537 (8)	−0.0198 (6)	0.0006 (6)	0.0000 (5)
C6	0.0429 (6)	0.0349 (6)	0.0467 (7)	−0.0207 (5)	0.0035 (5)	−0.0073 (5)
C7	0.0499 (7)	0.0449 (7)	0.0560 (8)	−0.0275 (6)	0.0010 (6)	−0.0124 (6)
C8	0.0510 (8)	0.0786 (10)	0.0469 (8)	−0.0337 (8)	−0.0057 (6)	−0.0141 (7)
C9	0.0516 (8)	0.0773 (11)	0.0546 (9)	−0.0345 (8)	−0.0082 (7)	−0.0023 (8)
C10	0.0568 (9)	0.0864 (13)	0.0607 (10)	−0.0308 (9)	−0.0006 (8)	−0.0034 (9)
N1	0.0444 (6)	0.0458 (6)	0.0413 (6)	−0.0250 (5)	−0.0048 (4)	−0.0006 (5)
N2	0.0453 (6)	0.0548 (7)	0.0453 (6)	−0.0280 (5)	−0.0021 (5)	−0.0107 (5)
N3	0.0516 (6)	0.0404 (6)	0.0563 (7)	−0.0284 (5)	−0.0044 (5)	−0.0006 (5)
O1	0.1353 (13)	0.0694 (8)	0.0879 (9)	−0.0731 (9)	−0.0361 (9)	0.0031 (7)
O2	0.0785 (8)	0.0473 (6)	0.0881 (9)	−0.0373 (6)	−0.0305 (7)	0.0222 (6)
C11	0.0350 (5)	0.0359 (6)	0.0385 (6)	−0.0185 (5)	−0.0107 (4)	0.0035 (5)
C12	0.0354 (6)	0.0328 (5)	0.0394 (6)	−0.0171 (5)	−0.0079 (5)	0.0029 (4)
C13	0.0454 (7)	0.0467 (7)	0.0396 (6)	−0.0214 (6)	−0.0047 (5)	0.0012 (5)
C14	0.0592 (8)	0.0515 (8)	0.0484 (8)	−0.0214 (7)	−0.0056 (6)	−0.0131 (6)
C15	0.0601 (9)	0.0393 (7)	0.0652 (9)	−0.0229 (6)	−0.0165 (7)	−0.0084 (6)
C16	0.0457 (7)	0.0371 (6)	0.0532 (7)	−0.0236 (5)	−0.0165 (6)	0.0061 (5)
C17	0.0574 (8)	0.0509 (8)	0.0655 (9)	−0.0363 (7)	−0.0199 (7)	0.0172 (7)
C18	0.0548 (9)	0.0939 (13)	0.0546 (9)	−0.0423 (9)	−0.0056 (7)	0.0238 (9)
C19	0.0529 (8)	0.0657 (9)	0.0513 (8)	−0.0303 (7)	−0.0036 (6)	0.0144 (7)
C20	0.0687 (11)	0.0900 (13)	0.0579 (10)	−0.0402 (10)	0.0091 (8)	0.0004 (9)
N4	0.0441 (6)	0.0490 (6)	0.0400 (5)	−0.0257 (5)	−0.0059 (4)	0.0048 (5)
N5	0.0500 (6)	0.0615 (7)	0.0476 (6)	−0.0354 (6)	−0.0112 (5)	0.0162 (5)
N6	0.0421 (5)	0.0377 (5)	0.0482 (6)	−0.0223 (5)	−0.0070 (5)	0.0026 (4)
O3	0.0892 (8)	0.0508 (6)	0.0500 (6)	−0.0399 (6)	−0.0076 (5)	−0.0067 (5)
O4	0.0824 (8)	0.0530 (6)	0.0815 (8)	−0.0439 (6)	0.0186 (7)	0.0003 (6)

C1—N1	1.3459 (17)	C11—N4	1.3459 (16)
C1—C2	1.4208 (17)	C11—C12	1.4196 (17)
C1—C6	1.4337 (17)	C11—C16	1.4313 (17)
C2—C3	1.3648 (18)	C12—C13	1.3686 (18)
C2—N3	1.4517 (16)	C12—N6	1.4509 (16)
C3—C4	1.409 (2)	C13—C14	1.407 (2)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.358 (2)	C14—C15	1.358 (2)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.402 (2)	C15—C16	1.403 (2)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.389 (2)	C16—C17	1.391 (2)
C7—N2	1.330 (2)	C17—N5	1.326 (2)
C7—H7	0.9300	C17—H17	0.9300
C8—N2	1.4649 (19)	C18—N5	1.469 (2)
C8—C9	1.489 (2)	C18—C19	1.486 (2)
C8—H8A	0.9700	C18—H18A	0.9700
C8—H8B	0.9700	C18—H18B	0.9700
C9—C10	1.279 (2)	C19—C20	1.304 (3)
C9—H9	0.9300	C19—H19	0.9300
C10—H10A	0.9300	C20—H20A	0.9300
C10—H10B	0.9300	C20—H20B	0.9300
N1—N2	1.3615 (16)	N4—N5	1.3605 (16)
N3—O2	1.2137 (16)	N6—O3	1.2240 (15)
N3—O1	1.2207 (17)	N6—O4	1.2292 (15)
N1—C1—C2	131.9 (2)	N4—C11—C12	131.5 (2)
N1—C1—C6	111.6 (2)	N4—C11—C16	111.7 (2)
C2—C1—C6	116.5 (2)	C12—C11—C16	116.8 (2)
C3—C2—C1	120.6 (2)	C13—C12—C11	120.6 (2)
C3—C2—N3	118.2 (2)	C13—C12—N6	118.2 (2)
C1—C2—N3	121.3 (2)	C11—C12—N6	121.2 (2)
C2—C3—C4	121.2 (2)	C12—C13—C14	120.8 (2)
C2—C3—H3	119.4	C12—C13—H13	119.6
C4—C3—H3	119.4	C14—C13—H13	119.6
C5—C4—C3	120.8 (2)	C15—C14—C13	121.2 (2)
C5—C4—H4	119.6	C15—C14—H14	119.4
C3—C4—H4	119.6	C13—C14—H14	119.4
C4—C5—C6	118.9 (2)	C14—C15—C16	118.8 (2)
C4—C5—H5	120.6	C14—C15—H15	120.6
C6—C5—H5	120.6	C16—C15—H15	120.6
C7—C6—C5	134.0 (2)	C17—C16—C15	134.4 (2)
C7—C6—C1	104.0 (2)	C17—C16—C11	103.8 (2)
C5—C6—C1	121.9 (2)	C15—C16—C11	121.8 (2)
N2—C7—C6	106.6 (2)	N5—C17—C16	106.7 (2)
N2—C7—H7	126.7	N5—C17—H17	126.6
C6—C7—H7	126.7	C16—C17—H17	126.6
N2—C8—C9	114.9 (2)	N5—C18—C19	113.1 (2)
N2—C8—H8A	108.5	N5—C18—H18A	109.0
C9—C8—H8A	108.5	C19—C18—H18A	109.0
N2—C8—H8B	108.5	N5—C18—H18B	109.0
C9—C8—H8B	108.5	C19—C18—H18B	109.0
H8A—C8—H8B	107.5	H18A—C18—H18B	107.8
C10—C9—C8	127.5 (2)	C20—C19—C18	123.8 (2)
C10—C9—H9	116.3	C20—C19—H19	118.1
C8—C9—H9	116.3	C18—C19—H19	118.1
C9—C10—H10A	120.0	C19—C20—H20A	120.0
C9—C10—H10B	120.0	C19—C20—H20B	120.0
H10A—C10—H10B	120.0	H20A—C20—H20B	120.0
C1—N1—N2	103.1 (2)	C11—N4—N5	103.0 (2)
C7—N2—N1	114.7 (2)	C17—N5—N4	114.8 (2)
C7—N2—C8	126.3 (2)	C17—N5—C18	126.9 (2)
N1—N2—C8	119.0 (2)	N4—N5—C18	118.3 (2)
O2—N3—O1	122.8 (2)	O3—N6—O4	122.8 (2)
O2—N3—C2	118.7 (2)	O3—N6—C12	118.6 (2)
O1—N3—C2	118.5 (2)	O4—N6—C12	118.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···N2	0.93	2.60	2.907 (3)	100
C5—H5···O1i	0.93	2.49	3.4004 (19)	165
C8—H8A···O4ii	0.97	2.45	3.205 (2)	134
C15—H15···O4i	0.93	2.49	3.3986 (19)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯N2	0.93	2.60	2.907 (3)	100
C5—H5⋯O1i	0.93	2.49	3.4004 (19)	165
C8—H8A⋯O4ii	0.97	2.45	3.205 (2)	134
C15—H15⋯O4i	0.93	2.49	3.3986 (19)	167

Symmetry codes: (i) ; (ii) .