1-Allyl-3-chloro-5-nitro-1H-indazole.

In the title compound, C10H8ClN3O2, the indazole ring system makes a dihedral angle of 7.9 (3)° with the plane through the nitro group. The allyl group is rotated out of the plane of the indazole ring system [N-N-C-C torsion angle = 104.28 (19)°]. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming zigzag chains propagating along the b-axis direction.

Related literature

For the pharmacological activity of indazole derivatives, see: Baraldi et al. (2001 ▶); Rodgers et al. (1996 ▶); Li et al. (2003 ▶); Lin et al. (2008 ▶). For a similar compound, see: El Brahmi et al. (2012 ▶).

Experimental

Crystal data

C10H8ClN3O2

M = 237.64

Monoclinic,

a = 13.3025 (6) Å

b = 11.2505 (5) Å

c = 7.3092 (3) Å

β = 91.343 (2)°

V = 1093.59 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 296 K

0.41 × 0.34 × 0.22 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS: Sheldrick, 2008 ▶) T min = 0.654, T max = 0.747

14430 measured reflections

3069 independent reflections

1852 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.136

S = 1.02

3069 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.33 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/S1600536813021995/bt6927sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021995/bt6927Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021995/bt6927Isup3.cml

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

C10H8ClN3O2	F(000) = 488
Mr = 237.64	Dx = 1.443 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3069 reflections
a = 13.3025 (6) Å	θ = 2.4–29.6°
b = 11.2505 (5) Å	µ = 0.34 mm−1
c = 7.3092 (3) Å	T = 296 K
β = 91.343 (2)°	Block, colourless
V = 1093.59 (8) Å3	0.41 × 0.34 × 0.22 mm
Z = 4

Bruker X8 APEX diffractometer	3069 independent reflections
Radiation source: fine-focus sealed tube	1852 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 29.6°, θmin = 2.4°
Absorption correction: multi-scan (SADABS: Sheldrick, 2008)	h = −18→18
Tmin = 0.654, Tmax = 0.747	k = −10→15
14430 measured reflections	l = −9→10

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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F2) = 0.136	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.069P)2 + 0.0517P] where P = (Fo2 + 2Fc2)/3
3069 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.33 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
C1	0.39644 (11)	0.25338 (16)	1.0420 (2)	0.0451 (4)
C2	0.29681 (11)	0.22952 (14)	0.97697 (19)	0.0415 (4)
C3	0.24119 (12)	0.12846 (15)	0.9339 (2)	0.0462 (4)
H3	0.2681	0.0525	0.9450	0.055*
C4	0.14423 (13)	0.14758 (16)	0.8741 (2)	0.0517 (4)
C5	0.10115 (12)	0.26115 (18)	0.8562 (2)	0.0549 (5)
H5	0.0346	0.2685	0.8160	0.066*
C6	0.15549 (13)	0.36043 (16)	0.8970 (2)	0.0508 (4)
H6	0.1278	0.4360	0.8848	0.061*
C7	0.25499 (12)	0.34380 (14)	0.9583 (2)	0.0428 (4)
C8	0.32262 (15)	0.55248 (16)	1.0068 (3)	0.0596 (5)
H8A	0.3794	0.5846	1.0763	0.071*
H8B	0.2616	0.5785	1.0650	0.071*
C9	0.32387 (17)	0.59986 (17)	0.8194 (3)	0.0666 (5)
H9	0.3814	0.5866	0.7526	0.080*
C10	0.2520 (2)	0.6582 (2)	0.7404 (5)	0.1088 (10)
H10A	0.1931	0.6734	0.8025	0.131*
H10B	0.2588	0.6852	0.6210	0.131*
N1	0.32739 (10)	0.42252 (13)	1.01153 (19)	0.0492 (4)
N2	0.41482 (10)	0.36715 (13)	1.06173 (19)	0.0503 (4)
N3	0.08324 (14)	0.04395 (18)	0.8226 (2)	0.0720 (5)
O1	0.12321 (14)	−0.05345 (16)	0.8167 (3)	0.0968 (6)
O2	−0.00516 (13)	0.06089 (18)	0.7844 (3)	0.1118 (7)
Cl1	0.48743 (3)	0.15046 (5)	1.08995 (7)	0.0677 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0412 (8)	0.0522 (10)	0.0417 (8)	0.0014 (7)	−0.0009 (6)	0.0049 (7)
C2	0.0419 (8)	0.0462 (9)	0.0364 (7)	−0.0014 (7)	0.0006 (6)	0.0022 (7)
C3	0.0520 (10)	0.0463 (9)	0.0404 (8)	−0.0039 (7)	0.0034 (7)	0.0008 (7)
C4	0.0497 (10)	0.0619 (12)	0.0435 (8)	−0.0181 (8)	0.0021 (7)	−0.0055 (8)
C5	0.0388 (9)	0.0757 (13)	0.0500 (10)	−0.0016 (9)	−0.0047 (7)	−0.0016 (9)
C6	0.0458 (9)	0.0567 (11)	0.0498 (9)	0.0071 (8)	−0.0024 (7)	0.0017 (8)
C7	0.0428 (8)	0.0458 (9)	0.0398 (8)	−0.0012 (7)	−0.0008 (6)	0.0017 (7)
C8	0.0678 (12)	0.0427 (10)	0.0679 (12)	−0.0045 (8)	−0.0037 (9)	−0.0069 (8)
C9	0.0795 (14)	0.0424 (11)	0.0778 (13)	−0.0081 (10)	−0.0029 (11)	0.0029 (10)
C10	0.139 (3)	0.0582 (14)	0.127 (2)	−0.0137 (14)	−0.056 (2)	0.0176 (14)
N1	0.0485 (8)	0.0440 (8)	0.0548 (8)	−0.0036 (6)	−0.0071 (6)	0.0020 (6)
N2	0.0438 (8)	0.0544 (9)	0.0523 (8)	−0.0044 (6)	−0.0057 (6)	0.0045 (7)
N3	0.0667 (11)	0.0798 (13)	0.0694 (11)	−0.0279 (10)	0.0027 (9)	−0.0118 (10)
O1	0.0979 (12)	0.0673 (11)	0.1254 (15)	−0.0298 (10)	0.0049 (11)	−0.0242 (10)
O2	0.0639 (10)	0.1174 (15)	0.1528 (18)	−0.0334 (10)	−0.0243 (10)	−0.0240 (12)
Cl1	0.0516 (3)	0.0709 (4)	0.0803 (4)	0.0142 (2)	−0.0084 (2)	0.0080 (2)

C1—N2	1.310 (2)	C7—N1	1.359 (2)
C1—C2	1.423 (2)	C8—N1	1.464 (2)
C1—Cl1	1.7056 (17)	C8—C9	1.470 (3)
C2—C3	1.389 (2)	C8—H8A	0.9700
C2—C7	1.406 (2)	C8—H8B	0.9700
C3—C4	1.369 (2)	C9—C10	1.286 (3)
C3—H3	0.9300	C9—H9	0.9300
C4—C5	1.405 (3)	C10—H10A	0.9300
C4—N3	1.465 (2)	C10—H10B	0.9300
C5—C6	1.360 (2)	N1—N2	1.3621 (19)
C5—H5	0.9300	N3—O2	1.217 (2)
C6—C7	1.400 (2)	N3—O1	1.219 (2)
C6—H6	0.9300
N2—C1—C2	113.02 (14)	C6—C7—C2	121.48 (15)
N2—C1—Cl1	120.71 (12)	N1—C8—C9	112.52 (16)
C2—C1—Cl1	126.27 (14)	N1—C8—H8A	109.1
C3—C2—C7	121.26 (15)	C9—C8—H8A	109.1
C3—C2—C1	135.84 (16)	N1—C8—H8B	109.1
C7—C2—C1	102.90 (14)	C9—C8—H8B	109.1
C4—C3—C2	115.89 (16)	H8A—C8—H8B	107.8
C4—C3—H3	122.1	C10—C9—C8	125.4 (3)
C2—C3—H3	122.1	C10—C9—H9	117.3
C3—C4—C5	123.49 (16)	C8—C9—H9	117.3
C3—C4—N3	117.96 (18)	C9—C10—H10A	120.0
C5—C4—N3	118.54 (17)	C9—C10—H10B	120.0
C6—C5—C4	120.86 (16)	H10A—C10—H10B	120.0
C6—C5—H5	119.6	C7—N1—N2	111.97 (13)
C4—C5—H5	119.6	C7—N1—C8	127.90 (15)
C5—C6—C7	117.01 (16)	N2—N1—C8	119.96 (14)
C5—C6—H6	121.5	C1—N2—N1	105.13 (13)
C7—C6—H6	121.5	O2—N3—O1	123.54 (19)
N1—C7—C6	131.54 (16)	O2—N3—C4	117.4 (2)
N1—C7—C2	106.97 (14)	O1—N3—C4	119.02 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.93	2.46	3.274 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.93	2.46	3.274 (2)	146

Symmetry code: (i) .