1-Allyl-3-chloro-6-nitro-1H-indazole.

The indazole system in each of the two independent mol-ecules of the title compound, C(10)H(8)ClN(3)O(2), is planar (r.m.s. deviations = 0.005 and 0.005 Å). The nitro group is coplanar with the fused-ring system [dihedral angles = 1.3 (3) and 4.8 (3) Å].

Related literature

For a review of indazoles, see: Elguéro (1996 ▶); Elguéro et al. (1995 ▶).

Experimental

Crystal data

C10H8ClN3O2

M = 237.64

Monoclinic,

a = 7.6804 (1) Å

b = 9.9559 (2) Å

c = 28.4344 (4) Å

β = 95.144 (1)°

V = 2165.49 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.34 mm−1

T = 295 K

0.4 × 0.3 × 0.2 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.884, T max = 0.934

19833 measured reflections

3777 independent reflections

2665 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.185

S = 1.07

3777 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034138/tk2531sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809034138/tk2531Isup2.hkl

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

C10H8ClN3O2	F(000) = 976
Mr = 237.64	Dx = 1.458 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6549 reflections
a = 7.6804 (1) Å	θ = 2.2–29.5°
b = 9.9559 (2) Å	µ = 0.34 mm−1
c = 28.4344 (4) Å	T = 295 K
β = 95.144 (1)°	Prism, yellow
V = 2165.49 (6) Å3	0.4 × 0.3 × 0.2 mm
Z = 8

Bruker APEX2 diffractometer	3777 independent reflections
Radiation source: fine-focus sealed tube	2665 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.884, Tmax = 0.934	k = −11→11
19833 measured reflections	l = −33→33

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1031P)2 + 0.7179P] where P = (Fo2 + 2Fc2)/3
3777 reflections	(Δ/σ)max = 0.001
289 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
Cl1	0.30814 (12)	0.06578 (10)	0.03474 (3)	0.0718 (3)
Cl2	0.94159 (18)	0.35838 (12)	0.02733 (4)	0.0958 (4)
O1	0.6481 (4)	0.0762 (3)	0.28950 (9)	0.0866 (9)
O2	0.7296 (4)	0.2788 (3)	0.27899 (9)	0.0867 (9)
O3	1.2186 (4)	0.2329 (4)	0.28256 (10)	0.1089 (11)
O4	1.0809 (4)	0.0460 (3)	0.27538 (10)	0.0928 (9)
N1	0.5287 (3)	0.3527 (3)	0.10386 (9)	0.0563 (7)
N2	0.4505 (4)	0.2960 (3)	0.06380 (9)	0.0606 (8)
N3	0.6601 (4)	0.1750 (3)	0.26458 (9)	0.0582 (7)
N4	0.8630 (3)	0.0501 (3)	0.09910 (10)	0.0529 (7)
N5	0.8504 (4)	0.1220 (3)	0.05846 (10)	0.0622 (8)
N6	1.1300 (4)	0.1509 (4)	0.25934 (11)	0.0659 (8)
C1	0.4072 (4)	0.1742 (4)	0.07565 (11)	0.0523 (8)
C2	0.4547 (3)	0.1450 (3)	0.12352 (11)	0.0451 (7)
C3	0.4413 (4)	0.0352 (3)	0.15351 (11)	0.0509 (8)
H3	0.3882	−0.0441	0.1424	0.061*
C4	0.5079 (4)	0.0470 (3)	0.19951 (11)	0.0510 (8)
H4	0.5003	−0.0244	0.2203	0.061*
C5	0.5876 (4)	0.1675 (3)	0.21511 (10)	0.0458 (7)
C6	0.6039 (4)	0.2781 (3)	0.18747 (10)	0.0447 (7)
H6	0.6570	0.3568	0.1991	0.054*
C7	0.5353 (4)	0.2648 (3)	0.14059 (11)	0.0447 (7)
C8	0.6026 (5)	0.4877 (4)	0.10227 (14)	0.0678 (10)
H8A	0.6737	0.5039	0.1317	0.081*
H8B	0.6793	0.4909	0.0770	0.081*
C9	0.4777 (6)	0.5939 (5)	0.0952 (2)	0.0994 (15)
H9	0.4034	0.6041	0.1191	0.119*
C10	0.4537 (7)	0.6752 (5)	0.0618 (2)	0.1091 (18)
H10A	0.5232	0.6710	0.0366	0.131*
H10B	0.3663	0.7398	0.0620	0.131*
C11	0.9279 (4)	0.2371 (4)	0.06933 (11)	0.0588 (9)
C12	0.9941 (4)	0.2448 (3)	0.11660 (11)	0.0488 (8)
C13	1.0839 (4)	0.3397 (3)	0.14605 (13)	0.0563 (8)
H13	1.1130	0.4232	0.1343	0.068*
C14	1.1278 (4)	0.3072 (4)	0.19233 (13)	0.0563 (9)
H14	1.1885	0.3681	0.2124	0.068*
C15	1.0808 (4)	0.1816 (3)	0.20921 (11)	0.0491 (8)
C16	0.9938 (3)	0.0852 (3)	0.18217 (11)	0.0453 (7)
H16	0.9651	0.0023	0.1944	0.054*
C17	0.9510 (3)	0.1194 (3)	0.13522 (11)	0.0435 (7)
C18	0.8035 (4)	−0.0888 (3)	0.09845 (13)	0.0615 (9)
H18A	0.6969	−0.0963	0.0776	0.074*
H18B	0.7766	−0.1142	0.1299	0.074*
C19	0.9352 (5)	−0.1820 (4)	0.08251 (14)	0.0701 (10)
H19	0.9748	−0.1658	0.0531	0.084*
C20	0.9988 (6)	−0.2813 (5)	0.1052 (2)	0.1019 (16)
H20A	0.9629	−0.3012	0.1348	0.122*
H20B	1.0817	−0.3350	0.0924	0.122*

	U11	U22	U33	U12	U13	U23
Cl1	0.0785 (6)	0.0739 (7)	0.0602 (6)	−0.0018 (5)	−0.0089 (4)	−0.0182 (4)
Cl2	0.1491 (11)	0.0756 (9)	0.0649 (6)	0.0153 (7)	0.0215 (6)	0.0187 (5)
O1	0.128 (2)	0.072 (2)	0.0577 (15)	0.0029 (16)	−0.0050 (15)	0.0184 (15)
O2	0.116 (2)	0.081 (2)	0.0593 (16)	−0.0218 (17)	−0.0108 (15)	−0.0064 (14)
O3	0.126 (2)	0.121 (3)	0.0733 (19)	−0.021 (2)	−0.0282 (18)	−0.0127 (19)
O4	0.133 (3)	0.074 (2)	0.0688 (18)	0.0066 (18)	−0.0030 (16)	0.0176 (16)
N1	0.0649 (16)	0.0493 (18)	0.0536 (16)	−0.0039 (13)	−0.0018 (12)	0.0018 (13)
N2	0.0677 (16)	0.063 (2)	0.0494 (16)	0.0022 (14)	−0.0031 (13)	−0.0010 (14)
N3	0.0651 (16)	0.060 (2)	0.0495 (16)	0.0074 (14)	0.0058 (13)	−0.0029 (15)
N4	0.0516 (14)	0.0464 (18)	0.0606 (17)	0.0000 (12)	0.0055 (12)	−0.0086 (13)
N5	0.0684 (17)	0.062 (2)	0.0560 (17)	0.0127 (15)	0.0025 (13)	−0.0061 (15)
N6	0.0645 (17)	0.071 (2)	0.0614 (19)	0.0134 (16)	−0.0007 (15)	−0.0084 (18)
C1	0.0503 (16)	0.053 (2)	0.0530 (19)	0.0056 (14)	0.0033 (14)	−0.0088 (16)
C2	0.0388 (14)	0.043 (2)	0.0543 (18)	0.0061 (12)	0.0063 (13)	−0.0087 (14)
C3	0.0506 (16)	0.041 (2)	0.062 (2)	0.0009 (13)	0.0101 (14)	−0.0064 (16)
C4	0.0567 (17)	0.042 (2)	0.0556 (19)	0.0068 (14)	0.0119 (15)	0.0031 (15)
C5	0.0443 (15)	0.047 (2)	0.0469 (17)	0.0094 (13)	0.0072 (13)	−0.0022 (14)
C6	0.0449 (15)	0.0386 (19)	0.0504 (17)	0.0050 (12)	0.0027 (13)	−0.0055 (14)
C7	0.0414 (14)	0.0427 (19)	0.0503 (17)	0.0079 (13)	0.0066 (12)	−0.0006 (15)
C8	0.078 (2)	0.054 (2)	0.069 (2)	−0.0089 (19)	−0.0050 (18)	0.0130 (18)
C9	0.085 (3)	0.078 (3)	0.134 (4)	−0.011 (2)	0.000 (3)	0.021 (3)
C10	0.108 (3)	0.080 (4)	0.132 (4)	−0.019 (3)	−0.023 (3)	0.046 (3)
C11	0.072 (2)	0.050 (2)	0.055 (2)	0.0154 (17)	0.0094 (17)	0.0019 (16)
C12	0.0496 (16)	0.040 (2)	0.0581 (18)	0.0094 (13)	0.0139 (14)	−0.0024 (15)
C13	0.0630 (19)	0.036 (2)	0.072 (2)	−0.0020 (14)	0.0176 (17)	−0.0019 (16)
C14	0.0510 (16)	0.047 (2)	0.072 (2)	−0.0019 (14)	0.0107 (15)	−0.0194 (17)
C15	0.0446 (15)	0.045 (2)	0.0577 (19)	0.0105 (13)	0.0057 (14)	−0.0034 (15)
C16	0.0460 (15)	0.0322 (18)	0.0589 (18)	0.0040 (12)	0.0105 (13)	0.0000 (14)
C17	0.0389 (14)	0.0354 (18)	0.0567 (18)	0.0060 (12)	0.0075 (13)	−0.0060 (14)
C18	0.0579 (18)	0.050 (2)	0.077 (2)	−0.0065 (15)	0.0049 (16)	−0.0166 (18)
C19	0.085 (2)	0.056 (3)	0.072 (2)	0.001 (2)	0.0204 (19)	−0.002 (2)
C20	0.096 (3)	0.082 (4)	0.131 (4)	0.013 (3)	0.030 (3)	0.027 (3)

Cl1—C1	1.714 (3)	C6—H6	0.9300
Cl2—C11	1.708 (4)	C8—C9	1.430 (6)
O1—N3	1.221 (4)	C8—H8A	0.9700
O2—N3	1.218 (4)	C8—H8B	0.9700
O3—N6	1.219 (4)	C9—C10	1.250 (6)
O4—N6	1.213 (4)	C9—H9	0.9300
N1—C7	1.360 (4)	C10—H10A	0.9300
N1—N2	1.362 (4)	C10—H10B	0.9300
N1—C8	1.461 (4)	C11—C12	1.396 (4)
N2—C1	1.309 (5)	C12—C13	1.402 (5)
N3—C5	1.468 (4)	C12—C17	1.408 (4)
N4—N5	1.356 (4)	C13—C14	1.368 (5)
N4—C17	1.365 (4)	C13—H13	0.9300
N4—C18	1.456 (4)	C14—C15	1.398 (5)
N5—C11	1.316 (5)	C14—H14	0.9300
N6—C15	1.474 (4)	C15—C16	1.367 (4)
C1—C2	1.408 (4)	C16—C17	1.388 (4)
C2—C3	1.396 (4)	C16—H16	0.9300
C2—C7	1.410 (4)	C18—C19	1.474 (5)
C3—C4	1.366 (4)	C18—H18A	0.9700
C3—H3	0.9300	C18—H18B	0.9700
C4—C5	1.401 (4)	C19—C20	1.255 (6)
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.365 (4)	C20—H20A	0.9300
C6—C7	1.395 (4)	C20—H20B	0.9300
C7—N1—N2	111.0 (3)	H8A—C8—H8B	107.5
C7—N1—C8	128.9 (3)	C10—C9—C8	129.6 (6)
N2—N1—C8	119.9 (3)	C10—C9—H9	115.2
C1—N2—N1	105.8 (3)	C8—C9—H9	115.2
O2—N3—O1	122.8 (3)	C9—C10—H10A	120.0
O2—N3—C5	118.9 (3)	C9—C10—H10B	120.0
O1—N3—C5	118.3 (3)	H10A—C10—H10B	120.0
N5—N4—C17	111.6 (3)	N5—C11—C12	113.1 (3)
N5—N4—C18	119.5 (3)	N5—C11—Cl2	120.4 (3)
C17—N4—C18	128.6 (3)	C12—C11—Cl2	126.5 (3)
C11—N5—N4	105.3 (3)	C11—C12—C13	136.8 (3)
O4—N6—O3	123.4 (4)	C11—C12—C17	103.6 (3)
O4—N6—C15	118.8 (3)	C13—C12—C17	119.5 (3)
O3—N6—C15	117.8 (4)	C14—C13—C12	118.7 (3)
N2—C1—C2	113.0 (3)	C14—C13—H13	120.6
N2—C1—Cl1	121.1 (3)	C12—C13—H13	120.6
C2—C1—Cl1	125.9 (3)	C13—C14—C15	119.6 (3)
C3—C2—C1	136.5 (3)	C13—C14—H14	120.2
C3—C2—C7	120.4 (3)	C15—C14—H14	120.2
C1—C2—C7	103.1 (3)	C16—C15—C14	124.3 (3)
C4—C3—C2	118.4 (3)	C16—C15—N6	117.9 (3)
C4—C3—H3	120.8	C14—C15—N6	117.8 (3)
C2—C3—H3	120.8	C15—C16—C17	115.5 (3)
C3—C4—C5	119.5 (3)	C15—C16—H16	122.2
C3—C4—H4	120.3	C17—C16—H16	122.2
C5—C4—H4	120.3	N4—C17—C16	131.2 (3)
C6—C5—C4	124.7 (3)	N4—C17—C12	106.4 (3)
C6—C5—N3	117.7 (3)	C16—C17—C12	122.4 (3)
C4—C5—N3	117.7 (3)	N4—C18—C19	112.2 (3)
C5—C6—C7	115.3 (3)	N4—C18—H18A	109.2
C5—C6—H6	122.4	C19—C18—H18A	109.2
C7—C6—H6	122.4	N4—C18—H18B	109.2
N1—C7—C6	131.1 (3)	C19—C18—H18B	109.2
N1—C7—C2	107.2 (3)	H18A—C18—H18B	107.9
C6—C7—C2	121.8 (3)	C20—C19—C18	125.7 (4)
C9—C8—N1	115.3 (3)	C20—C19—H19	117.1
C9—C8—H8A	108.5	C18—C19—H19	117.1
N1—C8—H8A	108.5	C19—C20—H20A	120.0
C9—C8—H8B	108.5	C19—C20—H20B	120.0
N1—C8—H8B	108.5	H20A—C20—H20B	120.0
C7—N1—N2—C1	0.7 (3)	N2—N1—C8—C9	70.4 (5)
C8—N1—N2—C1	176.4 (3)	N1—C8—C9—C10	−116.9 (5)
C17—N4—N5—C11	−1.0 (3)	N4—N5—C11—C12	0.3 (4)
C18—N4—N5—C11	−174.4 (3)	N4—N5—C11—Cl2	179.8 (2)
N1—N2—C1—C2	−0.2 (4)	N5—C11—C12—C13	−179.6 (3)
N1—N2—C1—Cl1	−178.6 (2)	Cl2—C11—C12—C13	0.9 (6)
N2—C1—C2—C3	−179.7 (3)	N5—C11—C12—C17	0.4 (3)
Cl1—C1—C2—C3	−1.4 (5)	Cl2—C11—C12—C17	−179.0 (2)
N2—C1—C2—C7	−0.3 (3)	C11—C12—C13—C14	−179.7 (3)
Cl1—C1—C2—C7	178.1 (2)	C17—C12—C13—C14	0.2 (4)
C1—C2—C3—C4	179.3 (3)	C12—C13—C14—C15	−0.7 (4)
C7—C2—C3—C4	0.0 (4)	C13—C14—C15—C16	0.9 (5)
C2—C3—C4—C5	−0.3 (4)	C13—C14—C15—N6	−179.7 (3)
C3—C4—C5—C6	0.5 (4)	O4—N6—C15—C16	−5.2 (4)
C3—C4—C5—N3	−179.0 (3)	O3—N6—C15—C16	174.8 (3)
O2—N3—C5—C6	0.7 (4)	O4—N6—C15—C14	175.4 (3)
O1—N3—C5—C6	−179.1 (3)	O3—N6—C15—C14	−4.6 (4)
O2—N3—C5—C4	−179.8 (3)	C14—C15—C16—C17	−0.5 (4)
O1—N3—C5—C4	0.4 (4)	N6—C15—C16—C17	−179.9 (2)
C4—C5—C6—C7	−0.5 (4)	N5—N4—C17—C16	−180.0 (3)
N3—C5—C6—C7	179.0 (2)	C18—N4—C17—C16	−7.3 (5)
N2—N1—C7—C6	179.3 (3)	N5—N4—C17—C12	1.3 (3)
C8—N1—C7—C6	4.0 (5)	C18—N4—C17—C12	174.0 (3)
N2—N1—C7—C2	−0.8 (3)	C15—C16—C17—N4	−178.6 (3)
C8—N1—C7—C2	−176.1 (3)	C15—C16—C17—C12	0.0 (4)
C5—C6—C7—N1	−180.0 (3)	C11—C12—C17—N4	−1.0 (3)
C5—C6—C7—C2	0.2 (4)	C13—C12—C17—N4	179.0 (3)
C3—C2—C7—N1	−179.8 (3)	C11—C12—C17—C16	−179.9 (3)
C1—C2—C7—N1	0.7 (3)	C13—C12—C17—C16	0.2 (4)
C3—C2—C7—C6	0.1 (4)	N5—N4—C18—C19	81.6 (4)
C1—C2—C7—C6	−179.5 (3)	C17—N4—C18—C19	−90.5 (4)
C7—N1—C8—C9	−114.7 (4)	N4—C18—C19—C20	123.4 (5)