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Acta Cryst. (2009). E65, o2320    [ doi:10.1107/S1600536809034138 ]

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

N. El Brahmi, B. Mohamed, E. M. Essassi, H. Zouihri and S. W. Ng

Abstract top

The indazole system in each of the two independent molecules of the title compound, C10H8ClN3O2, 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 top

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

Experimental top

3-Chloro-6-nitroindazole (5 mmol) and allyl bromide (10 mmol) were reacted in THF (40 ml) in the presence of potassium carbonate (10 mmol) and tetra-n-butylammonium bromide (0.5 mmol). The mixture was stirred for 24 h, filtered, and the THF removed under vacuum. The product was separated by chromatography on silica gel with a hexane:ethyl acetate (9:1) solvent system. The compound was obtained as yellow crystals in 50% yield; m.p. 351 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.97 Å) and were included in the refinement in the riding model approximation with U(H) set to 1.2U(C).

Although data were measured to a high 2θ limit, those reflections beyond 50 ° were not used as their inclusion significantly raised the R index.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C10H8ClN3O2 at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
1-Allyl-3-chloro-6-nitro-1H-indazole top
Crystal data top
C10H8ClN3O2F(000) = 976
Mr = 237.64Dx = 1.458 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6549 reflections
a = 7.6804 (1) Åθ = 2.2–29.5°
b = 9.9559 (2) ŵ = 0.34 mm−1
c = 28.4344 (4) ÅT = 295 K
β = 95.144 (1)°Prism, yellow
V = 2165.49 (6) Å30.4 × 0.3 × 0.2 mm
Z = 8
Data collection top
Bruker APEX2
diffractometer		3777 independent reflections
Radiation source: fine-focus sealed tube2665 reflections with I > 2σ(I)
graphiteRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −9→9
Tmin = 0.884, Tmax = 0.934k = −11→11
19833 measured reflectionsl = −33→33
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.185H-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 parametersΔρmax = 0.78 e Å−3
0 restraintsΔρmin = −0.29 e Å−3
Crystal data top
C10H8ClN3O2V = 2165.49 (6) Å3
Mr = 237.64Z = 8
Monoclinic, P21/nMo Kα radiation
a = 7.6804 (1) ŵ = 0.34 mm−1
b = 9.9559 (2) ÅT = 295 K
c = 28.4344 (4) Å0.4 × 0.3 × 0.2 mm
β = 95.144 (1)°
Data collection top
Bruker APEX2
diffractometer		2665 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.032
Tmin = 0.884, Tmax = 0.934θmax = 25.0°
19833 measured reflectionsStandard reflections: 0
3777 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.185Δρmax = 0.78 e Å−3
S = 1.07Δρmin = −0.29 e Å−3
3777 reflectionsAbsolute structure: ?
289 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.30814 (12)0.06578 (10)0.03474 (3)0.0718 (3)
Cl20.94159 (18)0.35838 (12)0.02733 (4)0.0958 (4)
O10.6481 (4)0.0762 (3)0.28950 (9)0.0866 (9)
O20.7296 (4)0.2788 (3)0.27899 (9)0.0867 (9)
O31.2186 (4)0.2329 (4)0.28256 (10)0.1089 (11)
O41.0809 (4)0.0460 (3)0.27538 (10)0.0928 (9)
N10.5287 (3)0.3527 (3)0.10386 (9)0.0563 (7)
N20.4505 (4)0.2960 (3)0.06380 (9)0.0606 (8)
N30.6601 (4)0.1750 (3)0.26458 (9)0.0582 (7)
N40.8630 (3)0.0501 (3)0.09910 (10)0.0529 (7)
N50.8504 (4)0.1220 (3)0.05846 (10)0.0622 (8)
N61.1300 (4)0.1509 (4)0.25934 (11)0.0659 (8)
C10.4072 (4)0.1742 (4)0.07565 (11)0.0523 (8)
C20.4547 (3)0.1450 (3)0.12352 (11)0.0451 (7)
C30.4413 (4)0.0352 (3)0.15351 (11)0.0509 (8)
H30.3882−0.04410.14240.061*
C40.5079 (4)0.0470 (3)0.19951 (11)0.0510 (8)
H40.5003−0.02440.22030.061*
C50.5876 (4)0.1675 (3)0.21511 (10)0.0458 (7)
C60.6039 (4)0.2781 (3)0.18747 (10)0.0447 (7)
H60.65700.35680.19910.054*
C70.5353 (4)0.2648 (3)0.14059 (11)0.0447 (7)
C80.6026 (5)0.4877 (4)0.10227 (14)0.0678 (10)
H8A0.67370.50390.13170.081*
H8B0.67930.49090.07700.081*
C90.4777 (6)0.5939 (5)0.0952 (2)0.0994 (15)
H90.40340.60410.11910.119*
C100.4537 (7)0.6752 (5)0.0618 (2)0.1091 (18)
H10A0.52320.67100.03660.131*
H10B0.36630.73980.06200.131*
C110.9279 (4)0.2371 (4)0.06933 (11)0.0588 (9)
C120.9941 (4)0.2448 (3)0.11660 (11)0.0488 (8)
C131.0839 (4)0.3397 (3)0.14605 (13)0.0563 (8)
H131.11300.42320.13430.068*
C141.1278 (4)0.3072 (4)0.19233 (13)0.0563 (9)
H141.18850.36810.21240.068*
C151.0808 (4)0.1816 (3)0.20921 (11)0.0491 (8)
C160.9938 (3)0.0852 (3)0.18217 (11)0.0453 (7)
H160.96510.00230.19440.054*
C170.9510 (3)0.1194 (3)0.13522 (11)0.0435 (7)
C180.8035 (4)−0.0888 (3)0.09845 (13)0.0615 (9)
H18A0.6969−0.09630.07760.074*
H18B0.7766−0.11420.12990.074*
C190.9352 (5)−0.1820 (4)0.08251 (14)0.0701 (10)
H190.9748−0.16580.05310.084*
C200.9988 (6)−0.2813 (5)0.1052 (2)0.1019 (16)
H20A0.9629−0.30120.13480.122*
H20B1.0817−0.33500.09240.122*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0785 (6)0.0739 (7)0.0602 (6)−0.0018 (5)−0.0089 (4)−0.0182 (4)
Cl20.1491 (11)0.0756 (9)0.0649 (6)0.0153 (7)0.0215 (6)0.0187 (5)
O10.128 (2)0.072 (2)0.0577 (15)0.0029 (16)−0.0050 (15)0.0184 (15)
O20.116 (2)0.081 (2)0.0593 (16)−0.0218 (17)−0.0108 (15)−0.0064 (14)
O30.126 (2)0.121 (3)0.0733 (19)−0.021 (2)−0.0282 (18)−0.0127 (19)
O40.133 (3)0.074 (2)0.0688 (18)0.0066 (18)−0.0030 (16)0.0176 (16)
N10.0649 (16)0.0493 (18)0.0536 (16)−0.0039 (13)−0.0018 (12)0.0018 (13)
N20.0677 (16)0.063 (2)0.0494 (16)0.0022 (14)−0.0031 (13)−0.0010 (14)
N30.0651 (16)0.060 (2)0.0495 (16)0.0074 (14)0.0058 (13)−0.0029 (15)
N40.0516 (14)0.0464 (18)0.0606 (17)0.0000 (12)0.0055 (12)−0.0086 (13)
N50.0684 (17)0.062 (2)0.0560 (17)0.0127 (15)0.0025 (13)−0.0061 (15)
N60.0645 (17)0.071 (2)0.0614 (19)0.0134 (16)−0.0007 (15)−0.0084 (18)
C10.0503 (16)0.053 (2)0.0530 (19)0.0056 (14)0.0033 (14)−0.0088 (16)
C20.0388 (14)0.043 (2)0.0543 (18)0.0061 (12)0.0063 (13)−0.0087 (14)
C30.0506 (16)0.041 (2)0.062 (2)0.0009 (13)0.0101 (14)−0.0064 (16)
C40.0567 (17)0.042 (2)0.0556 (19)0.0068 (14)0.0119 (15)0.0031 (15)
C50.0443 (15)0.047 (2)0.0469 (17)0.0094 (13)0.0072 (13)−0.0022 (14)
C60.0449 (15)0.0386 (19)0.0504 (17)0.0050 (12)0.0027 (13)−0.0055 (14)
C70.0414 (14)0.0427 (19)0.0503 (17)0.0079 (13)0.0066 (12)−0.0006 (15)
C80.078 (2)0.054 (2)0.069 (2)−0.0089 (19)−0.0050 (18)0.0130 (18)
C90.085 (3)0.078 (3)0.134 (4)−0.011 (2)0.000 (3)0.021 (3)
C100.108 (3)0.080 (4)0.132 (4)−0.019 (3)−0.023 (3)0.046 (3)
C110.072 (2)0.050 (2)0.055 (2)0.0154 (17)0.0094 (17)0.0019 (16)
C120.0496 (16)0.040 (2)0.0581 (18)0.0094 (13)0.0139 (14)−0.0024 (15)
C130.0630 (19)0.036 (2)0.072 (2)−0.0020 (14)0.0176 (17)−0.0019 (16)
C140.0510 (16)0.047 (2)0.072 (2)−0.0019 (14)0.0107 (15)−0.0194 (17)
C150.0446 (15)0.045 (2)0.0577 (19)0.0105 (13)0.0057 (14)−0.0034 (15)
C160.0460 (15)0.0322 (18)0.0589 (18)0.0040 (12)0.0105 (13)0.0000 (14)
C170.0389 (14)0.0354 (18)0.0567 (18)0.0060 (12)0.0075 (13)−0.0060 (14)
C180.0579 (18)0.050 (2)0.077 (2)−0.0065 (15)0.0049 (16)−0.0166 (18)
C190.085 (2)0.056 (3)0.072 (2)0.001 (2)0.0204 (19)−0.002 (2)
C200.096 (3)0.082 (4)0.131 (4)0.013 (3)0.030 (3)0.027 (3)
Geometric parameters (Å, °) top
Cl1—C11.714 (3)C6—H60.9300
Cl2—C111.708 (4)C8—C91.430 (6)
O1—N31.221 (4)C8—H8A0.9700
O2—N31.218 (4)C8—H8B0.9700
O3—N61.219 (4)C9—C101.250 (6)
O4—N61.213 (4)C9—H90.9300
N1—C71.360 (4)C10—H10A0.9300
N1—N21.362 (4)C10—H10B0.9300
N1—C81.461 (4)C11—C121.396 (4)
N2—C11.309 (5)C12—C131.402 (5)
N3—C51.468 (4)C12—C171.408 (4)
N4—N51.356 (4)C13—C141.368 (5)
N4—C171.365 (4)C13—H130.9300
N4—C181.456 (4)C14—C151.398 (5)
N5—C111.316 (5)C14—H140.9300
N6—C151.474 (4)C15—C161.367 (4)
C1—C21.408 (4)C16—C171.388 (4)
C2—C31.396 (4)C16—H160.9300
C2—C71.410 (4)C18—C191.474 (5)
C3—C41.366 (4)C18—H18A0.9700
C3—H30.9300C18—H18B0.9700
C4—C51.401 (4)C19—C201.255 (6)
C4—H40.9300C19—H190.9300
C5—C61.365 (4)C20—H20A0.9300
C6—C71.395 (4)C20—H20B0.9300
C7—N1—N2111.0 (3)H8A—C8—H8B107.5
C7—N1—C8128.9 (3)C10—C9—C8129.6 (6)
N2—N1—C8119.9 (3)C10—C9—H9115.2
C1—N2—N1105.8 (3)C8—C9—H9115.2
O2—N3—O1122.8 (3)C9—C10—H10A120.0
O2—N3—C5118.9 (3)C9—C10—H10B120.0
O1—N3—C5118.3 (3)H10A—C10—H10B120.0
N5—N4—C17111.6 (3)N5—C11—C12113.1 (3)
N5—N4—C18119.5 (3)N5—C11—Cl2120.4 (3)
C17—N4—C18128.6 (3)C12—C11—Cl2126.5 (3)
C11—N5—N4105.3 (3)C11—C12—C13136.8 (3)
O4—N6—O3123.4 (4)C11—C12—C17103.6 (3)
O4—N6—C15118.8 (3)C13—C12—C17119.5 (3)
O3—N6—C15117.8 (4)C14—C13—C12118.7 (3)
N2—C1—C2113.0 (3)C14—C13—H13120.6
N2—C1—Cl1121.1 (3)C12—C13—H13120.6
C2—C1—Cl1125.9 (3)C13—C14—C15119.6 (3)
C3—C2—C1136.5 (3)C13—C14—H14120.2
C3—C2—C7120.4 (3)C15—C14—H14120.2
C1—C2—C7103.1 (3)C16—C15—C14124.3 (3)
C4—C3—C2118.4 (3)C16—C15—N6117.9 (3)
C4—C3—H3120.8C14—C15—N6117.8 (3)
C2—C3—H3120.8C15—C16—C17115.5 (3)
C3—C4—C5119.5 (3)C15—C16—H16122.2
C3—C4—H4120.3C17—C16—H16122.2
C5—C4—H4120.3N4—C17—C16131.2 (3)
C6—C5—C4124.7 (3)N4—C17—C12106.4 (3)
C6—C5—N3117.7 (3)C16—C17—C12122.4 (3)
C4—C5—N3117.7 (3)N4—C18—C19112.2 (3)
C5—C6—C7115.3 (3)N4—C18—H18A109.2
C5—C6—H6122.4C19—C18—H18A109.2
C7—C6—H6122.4N4—C18—H18B109.2
N1—C7—C6131.1 (3)C19—C18—H18B109.2
N1—C7—C2107.2 (3)H18A—C18—H18B107.9
C6—C7—C2121.8 (3)C20—C19—C18125.7 (4)
C9—C8—N1115.3 (3)C20—C19—H19117.1
C9—C8—H8A108.5C18—C19—H19117.1
N1—C8—H8A108.5C19—C20—H20A120.0
C9—C8—H8B108.5C19—C20—H20B120.0
N1—C8—H8B108.5H20A—C20—H20B120.0
C7—N1—N2—C10.7 (3)N2—N1—C8—C970.4 (5)
C8—N1—N2—C1176.4 (3)N1—C8—C9—C10−116.9 (5)
C17—N4—N5—C11−1.0 (3)N4—N5—C11—C120.3 (4)
C18—N4—N5—C11−174.4 (3)N4—N5—C11—Cl2179.8 (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—C130.9 (6)
N2—C1—C2—C3−179.7 (3)N5—C11—C12—C170.4 (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—C7178.1 (2)C17—C12—C13—C140.2 (4)
C1—C2—C3—C4179.3 (3)C12—C13—C14—C15−0.7 (4)
C7—C2—C3—C40.0 (4)C13—C14—C15—C160.9 (5)
C2—C3—C4—C5−0.3 (4)C13—C14—C15—N6−179.7 (3)
C3—C4—C5—C60.5 (4)O4—N6—C15—C16−5.2 (4)
C3—C4—C5—N3−179.0 (3)O3—N6—C15—C16174.8 (3)
O2—N3—C5—C60.7 (4)O4—N6—C15—C14175.4 (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—C40.4 (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—C7179.0 (2)C18—N4—C17—C16−7.3 (5)
N2—N1—C7—C6179.3 (3)N5—N4—C17—C121.3 (3)
C8—N1—C7—C64.0 (5)C18—N4—C17—C12174.0 (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—C120.0 (4)
C5—C6—C7—N1−180.0 (3)C11—C12—C17—N4−1.0 (3)
C5—C6—C7—C20.2 (4)C13—C12—C17—N4179.0 (3)
C3—C2—C7—N1−179.8 (3)C11—C12—C17—C16−179.9 (3)
C1—C2—C7—N10.7 (3)C13—C12—C17—C160.2 (4)
C3—C2—C7—C60.1 (4)N5—N4—C18—C1981.6 (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—C20123.4 (5)
Acknowledgements top

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Elguéro, J. (1996). Comprehensive Heterocyclic Chemistry II, edited by I. Shinkai, Vol. 3, p. 1. Oxford: Elsevier Science.

Elguéro, J., Fruchier, A., Tjiou, E. M. & Trofimenko, S. (1995). Chem. Heterocycl. Compd (Engl. Transl.), 31, 1006–1026.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.