3-Bromo-6-nitro-1-(prop-2-yn-yl)-1H-indazole.

In the title compound, C(10)H(6)BrN(3)O(2), the indazole fused-ring system is nearly planar (r.m.s. deviation = 0.008 Å); its nitro substituent is nearly coplanar with the fused ring [dihedral angle = 4.5 (2)°]. In the crystal, adjacent mol-ecules are linked by weak acetyl-ene-nitro C-H⋯O hydrogen bonds, generating a helical chain running along the b axis.

Related literature

For a related compound, 1-allyl-3-chloro-6-nitro-1H-indazole, see: El Brahmi et al. (2009 ▶).

Experimental

Crystal data

C10H6BrN3O2

M = 280.09

Monoclinic,

a = 14.6573 (3) Å

b = 4.1650 (1) Å

c = 17.4566 (3) Å

β = 102.659 (1)°

V = 1039.78 (4) Å3

Z = 4

Mo Kα radiation

μ = 3.94 mm−1

T = 295 K

0.50 × 0.10 × 0.05 mm

Data collection

Bruker APEX DUO diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.243, T max = 0.827

14908 measured reflections

3137 independent reflections

2236 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.03

3137 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.76 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: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046927/xu5386sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046927/xu5386Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811046927/xu5386Isup3.cml

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

C10H6BrN3O2	F(000) = 552
Mr = 280.09	Dx = 1.789 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5822 reflections
a = 14.6573 (3) Å	θ = 2.4–30.3°
b = 4.1650 (1) Å	µ = 3.94 mm−1
c = 17.4566 (3) Å	T = 295 K
β = 102.659 (1)°	Plate, yellow
V = 1039.78 (4) Å3	0.50 × 0.10 × 0.05 mm
Z = 4

Bruker APEX DUO diffractometer	3137 independent reflections
Radiation source: fine-focus sealed tube	2236 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 30.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→20
Tmin = 0.243, Tmax = 0.827	k = −5→5
14908 measured reflections	l = −24→24

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0381P)2 + 0.4798P] where P = (Fo2 + 2Fc2)/3
3137 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.76 e Å−3

	x	y	z	Uiso*/Ueq
Br1	0.234567 (17)	0.49344 (5)	0.664925 (11)	0.03944 (9)
O1	0.44171 (11)	−0.5183 (4)	0.38032 (10)	0.0431 (4)
O2	0.30475 (11)	−0.5312 (3)	0.30395 (9)	0.0401 (4)
N1	0.11630 (11)	0.3405 (4)	0.52285 (9)	0.0296 (3)
N2	0.11523 (10)	0.1781 (4)	0.45461 (9)	0.0262 (3)
N3	0.35862 (11)	−0.4437 (4)	0.36351 (10)	0.0278 (3)
C1	0.20201 (14)	0.3105 (4)	0.56494 (10)	0.0281 (4)
C2	0.26030 (13)	0.1289 (4)	0.52666 (10)	0.0250 (4)
C3	0.35342 (14)	0.0226 (4)	0.54510 (11)	0.0287 (4)
H3	0.3930	0.0758	0.5927	0.034*
C4	0.38431 (13)	−0.1624 (4)	0.49070 (11)	0.0278 (4)
H4	0.4456	−0.2367	0.5011	0.033*
C5	0.32278 (12)	−0.2386 (4)	0.41932 (10)	0.0237 (3)
C6	0.23102 (12)	−0.1400 (4)	0.39812 (10)	0.0231 (3)
H6	0.1923	−0.1923	0.3501	0.028*
C7	0.20061 (12)	0.0457 (4)	0.45476 (11)	0.0226 (3)
C8	0.02773 (13)	0.1524 (5)	0.39593 (11)	0.0288 (4)
H8A	−0.0229	0.2344	0.4179	0.035*
H8B	0.0150	−0.0722	0.3831	0.035*
C9	0.03026 (13)	0.3299 (5)	0.32386 (11)	0.0293 (4)
C10	0.03171 (17)	0.4760 (5)	0.26605 (13)	0.0403 (5)
H1	0.033 (2)	0.595 (7)	0.2189 (19)	0.069 (9)*

	U11	U22	U33	U12	U13	U23
Br1	0.06481 (17)	0.03278 (12)	0.02030 (10)	0.00030 (9)	0.00838 (9)	−0.00163 (7)
O1	0.0298 (8)	0.0620 (11)	0.0371 (8)	0.0170 (7)	0.0068 (6)	−0.0001 (7)
O2	0.0352 (8)	0.0498 (9)	0.0340 (8)	0.0039 (6)	0.0049 (6)	−0.0132 (6)
N1	0.0398 (9)	0.0261 (8)	0.0257 (8)	0.0012 (7)	0.0131 (7)	0.0006 (6)
N2	0.0266 (8)	0.0284 (8)	0.0244 (7)	0.0018 (6)	0.0072 (6)	−0.0018 (6)
N3	0.0270 (8)	0.0301 (8)	0.0269 (8)	0.0028 (6)	0.0071 (6)	0.0046 (6)
C1	0.0415 (11)	0.0236 (8)	0.0199 (8)	−0.0026 (7)	0.0084 (7)	0.0014 (6)
C2	0.0319 (10)	0.0205 (8)	0.0220 (8)	−0.0023 (7)	0.0045 (7)	0.0034 (6)
C3	0.0310 (10)	0.0299 (9)	0.0220 (8)	−0.0045 (7)	−0.0012 (7)	0.0030 (7)
C4	0.0227 (9)	0.0292 (9)	0.0292 (9)	0.0002 (7)	0.0008 (7)	0.0053 (7)
C5	0.0245 (9)	0.0228 (8)	0.0241 (8)	−0.0010 (6)	0.0057 (7)	0.0039 (6)
C6	0.0238 (9)	0.0232 (8)	0.0218 (8)	−0.0023 (7)	0.0036 (6)	0.0012 (6)
C7	0.0235 (8)	0.0204 (8)	0.0236 (8)	−0.0016 (6)	0.0044 (7)	0.0029 (6)
C8	0.0239 (9)	0.0292 (9)	0.0335 (10)	−0.0003 (7)	0.0062 (7)	−0.0008 (7)
C9	0.0246 (9)	0.0323 (10)	0.0298 (9)	−0.0007 (7)	0.0032 (7)	−0.0060 (7)
C10	0.0429 (12)	0.0481 (13)	0.0283 (10)	−0.0086 (10)	0.0042 (9)	−0.0021 (9)

Br1—C1	1.8682 (17)	C3—H3	0.9300
O1—N3	1.228 (2)	C4—C5	1.405 (2)
O2—N3	1.216 (2)	C4—H4	0.9300
N1—C1	1.315 (2)	C5—C6	1.377 (2)
N1—N2	1.367 (2)	C6—C7	1.403 (2)
N2—C7	1.367 (2)	C6—H6	0.9300
N2—C8	1.459 (2)	C8—C9	1.467 (3)
N3—C5	1.476 (2)	C8—H8A	0.9700
C1—C2	1.414 (3)	C8—H8B	0.9700
C2—C7	1.407 (2)	C9—C10	1.183 (3)
C2—C3	1.403 (3)	C10—H1	0.96 (3)
C3—C4	1.374 (3)
C1—N1—N2	105.49 (15)	C5—C4—H4	120.2
N1—N2—C7	111.24 (15)	C6—C5—C4	124.76 (17)
N1—N2—C8	119.25 (15)	C6—C5—N3	117.59 (15)
C7—N2—C8	129.42 (15)	C4—C5—N3	117.65 (16)
O2—N3—O1	123.55 (17)	C5—C6—C7	114.68 (16)
O2—N3—C5	118.66 (15)	C5—C6—H6	122.7
O1—N3—C5	117.79 (16)	C7—C6—H6	122.7
N1—C1—C2	112.90 (15)	N2—C7—C6	130.79 (16)
N1—C1—Br1	120.03 (14)	N2—C7—C2	106.99 (16)
C2—C1—Br1	127.07 (14)	C6—C7—C2	122.22 (16)
C7—C2—C3	120.67 (17)	N2—C8—C9	112.42 (15)
C7—C2—C1	103.38 (16)	N2—C8—H8A	109.1
C3—C2—C1	135.92 (17)	C9—C8—H8A	109.1
C4—C3—C2	118.00 (17)	N2—C8—H8B	109.1
C4—C3—H3	121.0	C9—C8—H8B	109.1
C2—C3—H3	121.0	H8A—C8—H8B	107.9
C3—C4—C5	119.66 (17)	C10—C9—C8	179.2 (2)
C3—C4—H4	120.2	C9—C10—H1	180 (2)
C1—N1—N2—C7	0.35 (19)	O1—N3—C5—C4	−4.7 (2)
C1—N1—N2—C8	177.07 (15)	C4—C5—C6—C7	−0.9 (3)
N2—N1—C1—C2	−0.1 (2)	N3—C5—C6—C7	178.09 (15)
N2—N1—C1—Br1	−179.08 (12)	N1—N2—C7—C6	179.58 (17)
N1—C1—C2—C7	−0.2 (2)	C8—N2—C7—C6	3.3 (3)
Br1—C1—C2—C7	178.71 (13)	N1—N2—C7—C2	−0.49 (19)
N1—C1—C2—C3	−178.39 (19)	C8—N2—C7—C2	−176.79 (17)
Br1—C1—C2—C3	0.5 (3)	C5—C6—C7—N2	−178.79 (17)
C7—C2—C3—C4	0.4 (3)	C5—C6—C7—C2	1.3 (2)
C1—C2—C3—C4	178.4 (2)	C3—C2—C7—N2	178.93 (16)
C2—C3—C4—C5	0.0 (3)	C1—C2—C7—N2	0.41 (18)
C3—C4—C5—C6	0.2 (3)	C3—C2—C7—C6	−1.1 (3)
C3—C4—C5—N3	−178.71 (16)	C1—C2—C7—C6	−179.65 (16)
O2—N3—C5—C6	−4.2 (2)	N1—N2—C8—C9	112.94 (18)
O1—N3—C5—C6	176.26 (16)	C7—N2—C8—C9	−71.0 (2)
O2—N3—C5—C4	174.85 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H1···O1i	0.96 (3)	2.45 (3)	3.399 (3)	167 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H1⋯O1i	0.96 (3)	2.45 (3)	3.399 (3)	167 (3)

Symmetry code: (i) .