Crystal structure of 3-chloro-1-methyl-5-nitro-1H-indazole.

The mol-ecule of the title compound, C8H6ClN3O2, is built up from fused five- and six-membered rings connected to a chlorine atom and to nitro and methyl groups. The indazole system is essentially planar with the largest deviation from the mean plane being 0.007 (2) Å. No classical hydrogen bonds are observed in the structure. Two mol-ecules form a dimer organised by a symmetry centre via a close contact between a nitro-O atom and the chlorine atom [at 3.066 (2) Å this is shorter than the sum of their van der Waals radii].

Related literature

For biological activities such as as anti­microbial, anti­cancer, anti­inflammatory, anti­platelet and selective 5-HT6 antagonists of the title compound and derivatives, see: Schmidt et al. (2008 ▸); Shafakat Ali et al. (2012 ▸); Abbassi et al. (2014 ▸); Plescia et al. (2010 ▸); Lee et al. (2001 ▸); Liu et al. (2011 ▸).

Experimental

Crystal data

C8H6ClN3O2

M = 211.61

Monoclinic,

a = 3.8273 (2) Å

b = 14.678 (6) Å

c = 15.549 (6) Å

β = 96.130 (9)°

V = 868.5 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.41 mm−1

T = 296 K

0.31 × 0.27 × 0.21 mm

Data collection

Bruker X8 APEX Diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▸) T min = 0.654, T max = 0.747

19793 measured reflections

2243 independent reflections

1963 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.10

2243 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT (Bruker, 2009 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 (Burnett & Johnson, 1996 ▸; Farrugia, 2012 ▸); software used to prepare material for publication: publCIF (Westrip, 2010 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015018411/zp2019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015018411/zp2019Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015018411/zp2019Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015018411/zp2019fig1.tif

Plot of the mol­ecule of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

CCDC reference: 1429148

Additional supporting information: crystallographic information; 3D view; checkCIF report

C8H6ClN3O2	Dx = 1.618 Mg m−3
Mr = 211.61	Melting point: 471 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.8273 (2) Å	Cell parameters from 2243 reflections
b = 14.678 (6) Å	θ = 2.6–28.7°
c = 15.549 (6) Å	µ = 0.41 mm−1
β = 96.130 (9)°	T = 296 K
V = 868.5 (6) Å3	Block, colourless
Z = 4	0.31 × 0.27 × 0.21 mm
F(000) = 432

Bruker X8 APEX Diffractometer	2243 independent reflections
Radiation source: fine-focus sealed tube	1963 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
φ and ω scans	θmax = 28.7°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −5→5
Tmin = 0.654, Tmax = 0.747	k = −19→19
19793 measured reflections	l = −20→20

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0484P)2 + 0.5276P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2243 reflections	Δρmax = 0.36 e Å−3
127 parameters	Δρmin = −0.27 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.

	x	y	z	Uiso*/Ueq
Cl1	0.39641 (14)	0.41233 (3)	0.10469 (3)	0.04683 (17)
N3	0.7340 (4)	0.56202 (10)	0.29223 (9)	0.0345 (3)
N2	0.6938 (4)	0.48003 (10)	0.25083 (10)	0.0358 (3)
N1	0.0460 (5)	0.79442 (11)	0.05310 (10)	0.0416 (4)
O2	−0.0907 (5)	0.75957 (11)	−0.01323 (11)	0.0671 (5)
O1	0.0360 (6)	0.87596 (11)	0.06625 (11)	0.0669 (5)
C3	0.4260 (4)	0.59119 (11)	0.16618 (10)	0.0283 (3)
C4	0.5778 (4)	0.63052 (11)	0.24420 (10)	0.0299 (3)
C2	0.2473 (4)	0.64453 (11)	0.10193 (10)	0.0301 (3)
H2	0.1459	0.6196	0.0502	0.036*
C1	0.2289 (5)	0.73599 (12)	0.11912 (11)	0.0325 (3)
C7	0.5114 (4)	0.49799 (12)	0.17658 (11)	0.0320 (3)
C5	0.5521 (5)	0.72408 (12)	0.26022 (11)	0.0373 (4)
H5	0.6498	0.7497	0.3120	0.045*
C6	0.3773 (5)	0.77622 (12)	0.19662 (12)	0.0381 (4)
H6	0.3564	0.8387	0.2047	0.046*
C9	0.9194 (5)	0.56629 (15)	0.37845 (12)	0.0442 (5)
H9A	1.0018	0.5066	0.3957	0.066*
H9B	1.1160	0.6069	0.3785	0.066*
H9C	0.7634	0.5882	0.4182	0.066*

	U11	U22	U33	U12	U13	U23
Cl1	0.0591 (3)	0.0334 (2)	0.0457 (3)	0.00152 (19)	−0.0049 (2)	−0.01074 (18)
N3	0.0347 (8)	0.0374 (8)	0.0308 (7)	−0.0012 (6)	0.0006 (6)	−0.0012 (6)
N2	0.0367 (8)	0.0345 (7)	0.0360 (7)	0.0011 (6)	0.0033 (6)	−0.0012 (6)
N1	0.0497 (9)	0.0357 (8)	0.0405 (8)	0.0048 (7)	0.0095 (7)	0.0062 (6)
O2	0.0955 (14)	0.0476 (9)	0.0513 (9)	0.0052 (9)	−0.0246 (9)	0.0045 (7)
O1	0.1054 (15)	0.0352 (8)	0.0589 (10)	0.0147 (9)	0.0037 (9)	0.0054 (7)
C3	0.0266 (8)	0.0304 (8)	0.0285 (7)	−0.0028 (6)	0.0056 (6)	−0.0032 (6)
C4	0.0270 (8)	0.0348 (8)	0.0284 (7)	−0.0043 (6)	0.0051 (6)	−0.0020 (6)
C2	0.0310 (8)	0.0321 (8)	0.0276 (7)	−0.0024 (6)	0.0048 (6)	−0.0014 (6)
C1	0.0342 (9)	0.0315 (8)	0.0328 (8)	−0.0001 (7)	0.0084 (7)	0.0029 (6)
C7	0.0317 (8)	0.0314 (8)	0.0331 (8)	−0.0018 (6)	0.0047 (6)	−0.0039 (6)
C5	0.0430 (10)	0.0359 (9)	0.0330 (8)	−0.0069 (7)	0.0044 (7)	−0.0093 (7)
C6	0.0463 (10)	0.0283 (8)	0.0407 (9)	−0.0028 (7)	0.0100 (8)	−0.0058 (7)
C9	0.0422 (10)	0.0559 (12)	0.0326 (9)	−0.0021 (9)	−0.0055 (8)	−0.0008 (8)

Cl1—C7	1.7086 (18)	C4—C5	1.401 (2)
N3—C4	1.353 (2)	C2—C1	1.372 (2)
N3—N2	1.366 (2)	C2—H2	0.9300
N3—C9	1.450 (2)	C1—C6	1.406 (3)
N2—C7	1.311 (2)	C5—C6	1.367 (3)
N1—O1	1.215 (2)	C5—H5	0.9300
N1—O2	1.218 (2)	C6—H6	0.9300
N1—C1	1.458 (2)	C9—H9A	0.9600
C3—C2	1.390 (2)	C9—H9B	0.9600
C3—C4	1.411 (2)	C9—H9C	0.9600
C3—C7	1.412 (2)
C4—N3—N2	111.95 (14)	C2—C1—N1	117.97 (16)
C4—N3—C9	128.47 (16)	C6—C1—N1	118.43 (16)
N2—N3—C9	119.56 (16)	N2—C7—C3	113.01 (15)
C7—N2—N3	105.10 (14)	N2—C7—Cl1	120.27 (14)
O1—N1—O2	122.53 (18)	C3—C7—Cl1	126.72 (13)
O1—N1—C1	118.81 (17)	C6—C5—C4	117.27 (16)
O2—N1—C1	118.66 (16)	C6—C5—H5	121.4
C2—C3—C4	120.87 (15)	C4—C5—H5	121.4
C2—C3—C7	135.89 (15)	C5—C6—C1	120.43 (16)
C4—C3—C7	103.23 (14)	C5—C6—H6	119.8
N3—C4—C5	131.73 (16)	C1—C6—H6	119.8
N3—C4—C3	106.71 (15)	N3—C9—H9A	109.5
C5—C4—C3	121.56 (16)	N3—C9—H9B	109.5
C1—C2—C3	116.26 (15)	H9A—C9—H9B	109.5
C1—C2—H2	121.9	N3—C9—H9C	109.5
C3—C2—H2	121.9	H9A—C9—H9C	109.5
C2—C1—C6	123.60 (16)	H9B—C9—H9C	109.5