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

Mohamed Abdelahi, M.M.; El Bakri, Y.; Benchidmi, M.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314617018375

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 1| January 2018| x171837

https://doi.org/10.1107/S2414314617018375

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

Mohamed Mokhtar Mohamed Abdelahi,^a Youness El Bakri,^a Mohammed Benchidmi,^a ^* El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche des Sciences des médicaments, URAC 21, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: jalilmostafa202@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 20 December 2017; accepted 22 December 2017; online 9 January 2018)

The asymmetric unit of the title compound, C₁₀H₈BrN₃O₂, contains two independent molecules differing primarily in the orientations of the allyl substituents [N—C—C=C torsion angles = −125.4 (16) and 116.0 (16)°]. The crystal packing involves slipped π–π stacking of indazole units, together with weak C—H⋯O and C—H⋯Br hydrogen bonds. The crystal studied was refined as a two-component twin.

Keywords: crystal structure; hydrogen bond; π-stacking; indazole.

CCDC reference: 1813234

Structure description

Studies of the structure and physicochemical properties of the indazole ring have been reviewed (Abbassi et al., 2014 ; Li et al., 2003 ). As a continuation of our studies of indazole derivatives (Mohamed Abdelahi et al., 2017 ), we now report the synthesis and structure of the title compound (Fig. 1).

Figure 1
The asymmetric unit showing 50% probability ellipsoids.

The asymmetric unit consists of two independent molecules differing primarily in the orientations of the allyl group. Thus, the torsion angles N2—N1—C8—C9 and N5—N4—C18—C19 are, respectively, −77.9 (15) and −71.9 (15)° while the N1—C8—C9—C10 and N4—C18—C19—C20 torsion angles are, respectively, −125.4 (16) and 116.0 (16)°.

In the crystal, offset π–π stacking interactions between the N1/N2/C1/C2/C7 ring and the N4/N5/C11/C12/C17 ring at −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ form dimers with a dihedral angle between the ring planes of 3.9 (8)° and a centroid–centroid distance of 3.494 (8) Å. These dimers are arranged into two sets of oblique stacks, generally along the a-axis direction, by C4—H4⋯O1 and C18—H1B⋯O4 hydrogen bonds (Table 1 and Figs. 2–4 ). The normals to the stacks are inclined by +/-30.0 (8)° to [100] and by 44.7 (8)° to each other. Weak C—H⋯Br interactions are also observed (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1ⁱ	0.95	2.46	3.304 (16)	147
C18—H18B⋯O4ⁱⁱ	0.99	2.59	3.578 (16)	174
C9—H9⋯Br1ⁱⁱⁱ	0.95	3.09	3.814 (11)	134
C18—H18A⋯Br1^iv	0.99	2.91	3.770 (14)	146
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Detail of the intermolecular interactions. C—H⋯O and C—H⋯Br hydrogen bonds and the π-stacking interactions are shown, respectively, as black, light-orange and brown dashed lines.

Figure 3
Packing viewed along the a-axis direction with intermolecular interactions shown as in Fig. 2

Figure 4
Packing viewed along the b-axis direction with intermolecular interactions shown as in Fig. 2

Synthesis and crystallization

Allyl bromide (0.8 g, 5 mmol), potassium carbonate (1.24 g, 9 mmol) and a catalytic quantity of tetra-n-butylammonium iodide were added to a solution of 3-bromo-6-nitro-1H-indazole (0.6 g, 3 mmol) in tetrahydrofuran (30 ml). The mixture was stirred at room temperature for 48 h. The solution was then filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol solution to afford the title compound as pale-orange plates (yield: 67%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The model was refined as a two-component twin. The largest residual peaks in the final difference map are not in chemically reasonable positions to represent additional atoms. Possible sources may be inadequacies in the absorption corrections due to the large absorption coefficient and difficulties in accurately measuring the dimensions of the small crystal or a small amount of `whole molecule disorder' (ca 3%) with these peaks representing alternate locations of the bromine atoms but with peaks for the remainder of those molecules too small to be located confidently.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₈BrN₃O₂
M_r	282.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	7.5971 (4), 9.9501 (5), 28.5690 (13)
β (°)	95.086 (2)
V (Å³)	2151.08 (18)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	5.14
Crystal size (mm)	0.25 × 0.09 × 0.04

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (TWINABS; Sheldrick, 2009 )
T_min, T_max	0.36, 0.82
No. of measured, independent and observed [I > 2σ(I)] reflections	7880, 7639, 7050
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.217, 1.19
No. of reflections	7639
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.30, −1.22
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2016/6 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1813234

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314617018375/hb4194sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617018375/hb4194Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617018375/hb4194Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314617018375/hb4194Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

3-Bromo-6-nitro-1-(prop-2-en-1-yl)-1H-indazole top

Crystal data top

C₁₀H₈BrN₃O₂	F(000) = 1120
M_r = 282.10	D_x = 1.742 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 7.5971 (4) Å	Cell parameters from 7120 reflections
b = 9.9501 (5) Å	θ = 3.1–72.2°
c = 28.5690 (13) Å	µ = 5.14 mm⁻¹
β = 95.086 (2)°	T = 150 K
V = 2151.08 (18) Å³	Plate, pale orange
Z = 8	0.25 × 0.09 × 0.04 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	7639 independent reflections
Radiation source: INCOATEC IµS micro–focus source	7050 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.050
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.3°, θ_min = 3.1°
ω scans	h = −9→9
Absorption correction: multi-scan (TWINABS; Sheldrick, 2009)	k = −12→12
T_min = 0.36, T_max = 0.82	l = −34→34
7880 measured reflections

Refinement top

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.217	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0535P)² + 28.3909P] where P = (F_o² + 2F_c²)/3
7639 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 1.30 e Å⁻³
0 restraints	Δρ_min = −1.22 e Å⁻³

Special details top

Experimental. Analysis of 329 reflections having I/σ(I) > 12 and chosen from the full data set with CELL_NOW (Sheldrick, 2008) showed the crystal to belong to the monoclinic system and to be twinned by a 180° rotation about the c* axis. The raw data were processed using the multi-component version of SAINT under control of the two-component orientation file generated by CELL_NOW.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. Refined as a 2-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	0.5670 (2)	0.14543 (15)	0.47380 (4)	0.0448 (5)
O1	0.4189 (17)	0.4609 (11)	0.2213 (3)	0.052 (3)
O2	0.2730 (18)	0.2752 (12)	0.2166 (3)	0.061 (3)
N1	0.6482 (14)	0.4618 (10)	0.3968 (3)	0.029 (3)
N2	0.6614 (15)	0.3910 (11)	0.4374 (3)	0.033 (3)
N3	0.3656 (16)	0.3548 (12)	0.2383 (3)	0.034 (3)
C1	0.582 (2)	0.2767 (12)	0.4274 (4)	0.031 (3)
C2	0.5133 (18)	0.2658 (12)	0.3802 (4)	0.026 (3)
C3	0.4215 (18)	0.1720 (13)	0.3514 (4)	0.028 (3)
H3	0.391544	0.087488	0.363954	0.033*
C4	0.3747 (17)	0.1995 (12)	0.3060 (4)	0.025 (3)
H4	0.312848	0.134651	0.286457	0.030*
C5	0.4187 (16)	0.3267 (13)	0.2873 (4)	0.024 (3)
C6	0.5098 (16)	0.4257 (12)	0.3134 (4)	0.026 (3)
H6	0.540098	0.509440	0.300322	0.031*
C7	0.5544 (15)	0.3920 (12)	0.3613 (4)	0.022 (3)
C8	0.703 (2)	0.6038 (13)	0.3969 (4)	0.036 (3)
H8A	0.816224	0.613203	0.416593	0.043*
H8B	0.724045	0.630139	0.364414	0.043*
C9	0.5749 (19)	0.6947 (12)	0.4142 (4)	0.030 (3)
H9	0.537239	0.676754	0.444368	0.036*
C10	0.508 (2)	0.7977 (14)	0.3921 (5)	0.044 (4)
H10A	0.541706	0.819364	0.361763	0.053*
H10B	0.424128	0.852263	0.406066	0.053*
Br2	0.29479 (19)	0.94236 (14)	0.02996 (4)	0.0338 (4)
O3	0.7297 (14)	0.7347 (10)	0.2791 (3)	0.044 (3)
O4	0.6462 (16)	0.9375 (10)	0.2877 (3)	0.047 (3)
N4	0.5227 (15)	0.6482 (11)	0.1051 (3)	0.032 (3)
N5	0.4444 (16)	0.7016 (11)	0.0653 (3)	0.032 (3)
N6	0.6590 (16)	0.8373 (12)	0.2639 (3)	0.032 (3)
C11	0.3999 (17)	0.8278 (14)	0.0754 (4)	0.028 (3)
C12	0.4494 (18)	0.8587 (13)	0.1237 (4)	0.030 (3)
C13	0.4325 (18)	0.9707 (13)	0.1528 (4)	0.029 (3)
H13	0.374507	1.050083	0.141120	0.035*
C14	0.5014 (17)	0.9617 (13)	0.1977 (4)	0.030 (3)
H14	0.494502	1.036167	0.218244	0.036*
C15	0.5842 (18)	0.8410 (14)	0.2143 (4)	0.031 (3)
C16	0.5987 (18)	0.7294 (13)	0.1879 (4)	0.027 (3)
H16	0.652562	0.649426	0.200420	0.033*
C17	0.5295 (18)	0.7390 (12)	0.1410 (4)	0.026 (3)
C18	0.598 (2)	0.5136 (13)	0.1044 (4)	0.035 (3)
H18A	0.673729	0.507640	0.078086	0.042*
H18B	0.673545	0.499252	0.133934	0.042*
C19	0.468 (2)	0.4073 (14)	0.0994 (5)	0.044 (4)
H19	0.392167	0.395215	0.123703	0.053*
C20	0.450 (2)	0.3270 (16)	0.0632 (5)	0.051 (4)
H20A	0.524262	0.336954	0.038349	0.061*
H20B	0.362454	0.258601	0.061658	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0687 (11)	0.0364 (8)	0.0294 (6)	0.0046 (9)	0.0052 (8)	0.0051 (5)
O1	0.071 (8)	0.051 (7)	0.033 (4)	0.008 (6)	0.006 (5)	0.007 (4)
O2	0.076 (9)	0.071 (8)	0.032 (5)	−0.014 (8)	−0.017 (6)	−0.008 (5)
N1	0.038 (7)	0.027 (6)	0.023 (4)	−0.007 (6)	0.004 (4)	−0.006 (4)
N2	0.034 (7)	0.037 (7)	0.029 (5)	0.005 (6)	0.005 (5)	−0.001 (4)
N3	0.030 (6)	0.038 (7)	0.033 (5)	0.006 (7)	0.002 (5)	0.004 (5)
C1	0.042 (8)	0.023 (7)	0.027 (5)	0.009 (7)	0.003 (6)	0.000 (5)
C2	0.021 (6)	0.025 (6)	0.035 (6)	0.003 (7)	0.014 (5)	−0.004 (5)
C3	0.028 (7)	0.017 (6)	0.038 (6)	0.005 (6)	0.002 (6)	−0.002 (5)
C4	0.019 (6)	0.023 (6)	0.032 (5)	−0.007 (6)	0.004 (5)	−0.008 (4)
C5	0.020 (7)	0.020 (6)	0.033 (6)	0.002 (6)	0.005 (5)	−0.003 (5)
C6	0.019 (7)	0.021 (6)	0.038 (6)	0.008 (6)	0.003 (5)	0.000 (5)
C7	0.010 (6)	0.027 (6)	0.030 (5)	0.009 (6)	0.004 (5)	−0.006 (4)
C8	0.042 (9)	0.029 (7)	0.035 (6)	−0.012 (7)	0.002 (6)	−0.008 (5)
C9	0.037 (8)	0.024 (6)	0.030 (5)	0.005 (7)	0.004 (6)	−0.005 (5)
C10	0.041 (9)	0.039 (9)	0.053 (8)	0.000 (8)	0.005 (8)	0.009 (6)
Br2	0.0371 (7)	0.0342 (7)	0.0288 (5)	−0.0009 (7)	−0.0042 (6)	0.0048 (5)
O3	0.058 (7)	0.045 (6)	0.028 (4)	0.022 (6)	−0.005 (5)	0.007 (4)
O4	0.070 (7)	0.041 (6)	0.031 (4)	−0.005 (6)	−0.001 (5)	−0.012 (4)
N4	0.037 (7)	0.030 (6)	0.028 (5)	−0.001 (6)	−0.003 (4)	−0.001 (4)
N5	0.038 (7)	0.039 (6)	0.020 (4)	−0.001 (6)	−0.001 (5)	−0.002 (4)
N6	0.032 (7)	0.039 (7)	0.025 (4)	−0.001 (6)	−0.006 (5)	0.008 (5)
C11	0.022 (6)	0.036 (8)	0.024 (5)	−0.014 (7)	−0.003 (5)	−0.001 (5)
C12	0.028 (7)	0.030 (7)	0.030 (5)	−0.003 (7)	0.000 (5)	0.006 (5)
C13	0.030 (7)	0.024 (6)	0.033 (6)	−0.002 (7)	0.000 (5)	0.003 (5)
C14	0.024 (7)	0.028 (7)	0.037 (6)	−0.012 (7)	0.004 (5)	0.001 (5)
C15	0.037 (8)	0.039 (8)	0.018 (5)	−0.005 (7)	0.002 (5)	0.004 (5)
C16	0.029 (7)	0.026 (6)	0.025 (5)	−0.005 (7)	0.001 (5)	0.008 (5)
C17	0.026 (7)	0.021 (6)	0.030 (5)	−0.010 (6)	0.005 (5)	−0.007 (5)
C18	0.044 (9)	0.028 (7)	0.033 (6)	−0.003 (7)	0.004 (6)	−0.005 (5)
C19	0.050 (10)	0.034 (8)	0.048 (7)	0.002 (8)	0.002 (7)	−0.006 (6)
C20	0.053 (10)	0.041 (8)	0.055 (8)	0.005 (10)	−0.018 (8)	−0.014 (7)

Geometric parameters (Å, º) top

Br1—C1	1.872 (12)	Br2—C11	1.854 (12)
O1—N3	1.244 (15)	O3—N6	1.216 (14)
O2—N3	1.195 (15)	O4—N6	1.217 (14)
N1—N2	1.352 (13)	N4—N5	1.344 (14)
N1—C7	1.376 (14)	N4—C17	1.364 (15)
N1—C8	1.472 (16)	N4—C18	1.456 (17)
N2—C1	1.307 (16)	N5—C11	1.339 (17)
N3—C5	1.451 (15)	N6—C15	1.480 (13)
C1—C2	1.406 (17)	C11—C12	1.432 (15)
C2—C3	1.391 (18)	C12—C13	1.402 (17)
C2—C7	1.413 (17)	C12—C17	1.407 (18)
C3—C4	1.342 (16)	C13—C14	1.345 (16)
C3—H3	0.9500	C13—H13	0.9500
C4—C5	1.424 (17)	C14—C15	1.418 (19)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.383 (17)	C15—C16	1.352 (18)
C6—C7	1.420 (15)	C16—C17	1.399 (16)
C6—H6	0.9500	C16—H16	0.9500
C8—C9	1.448 (19)	C18—C19	1.44 (2)
C8—H8A	0.9900	C18—H18A	0.9900
C8—H8B	0.9900	C18—H18B	0.9900
C9—C10	1.285 (18)	C19—C20	1.304 (19)
C9—H9	0.9500	C19—H19	0.9500
C10—H10A	0.9500	C20—H20A	0.9500
C10—H10B	0.9500	C20—H20B	0.9500

N2—N1—C7	111.3 (10)	N5—N4—C17	111.0 (10)
N2—N1—C8	120.0 (9)	N5—N4—C18	119.7 (9)
C7—N1—C8	127.8 (10)	C17—N4—C18	129.1 (10)
C1—N2—N1	105.6 (9)	C11—N5—N4	106.8 (9)
O2—N3—O1	123.9 (11)	O3—N6—O4	122.8 (10)
O2—N3—C5	118.3 (11)	O3—N6—C15	119.0 (11)
O1—N3—C5	117.9 (11)	O4—N6—C15	118.2 (11)
N2—C1—C2	113.6 (11)	N5—C11—C12	111.1 (11)
N2—C1—Br1	120.6 (9)	N5—C11—Br2	121.8 (8)
C2—C1—Br1	125.8 (10)	C12—C11—Br2	127.1 (10)
C3—C2—C1	138.1 (12)	C13—C12—C17	121.7 (10)
C3—C2—C7	119.1 (11)	C13—C12—C11	135.4 (12)
C1—C2—C7	102.9 (11)	C17—C12—C11	102.9 (11)
C4—C3—C2	120.8 (12)	C14—C13—C12	117.6 (12)
C4—C3—H3	119.6	C14—C13—H13	121.2
C2—C3—H3	119.6	C12—C13—H13	121.2
C3—C4—C5	119.5 (11)	C13—C14—C15	119.9 (12)
C3—C4—H4	120.3	C13—C14—H14	120.0
C5—C4—H4	120.3	C15—C14—H14	120.0
C6—C5—C4	123.7 (11)	C16—C15—C14	124.4 (10)
C6—C5—N3	117.8 (11)	C16—C15—N6	118.0 (12)
C4—C5—N3	118.6 (11)	C14—C15—N6	117.6 (11)
C5—C6—C7	114.6 (11)	C15—C16—C17	115.8 (12)
C5—C6—H6	122.7	C15—C16—H16	122.1
C7—C6—H6	122.7	C17—C16—H16	122.1
N1—C7—C2	106.5 (10)	N4—C17—C16	131.4 (12)
N1—C7—C6	131.0 (11)	N4—C17—C12	108.1 (10)
C2—C7—C6	122.5 (11)	C16—C17—C12	120.5 (11)
C9—C8—N1	113.6 (12)	C19—C18—N4	114.3 (12)
C9—C8—H8A	108.8	C19—C18—H18A	108.7
N1—C8—H8A	108.8	N4—C18—H18A	108.7
C9—C8—H8B	108.8	C19—C18—H18B	108.7
N1—C8—H8B	108.8	N4—C18—H18B	108.7
H8A—C8—H8B	107.7	H18A—C18—H18B	107.6
C10—C9—C8	125.5 (13)	C20—C19—C18	123.5 (16)
C10—C9—H9	117.2	C20—C19—H19	118.3
C8—C9—H9	117.2	C18—C19—H19	118.3
C9—C10—H10A	120.0	C19—C20—H20A	120.0
C9—C10—H10B	120.0	C19—C20—H20B	120.0
H10A—C10—H10B	120.0	H20A—C20—H20B	120.0

C7—N1—N2—C1	1.8 (14)	C17—N4—N5—C11	−0.1 (15)
C8—N1—N2—C1	171.7 (12)	C18—N4—N5—C11	−175.7 (12)
N1—N2—C1—C2	0.3 (15)	N4—N5—C11—C12	−0.4 (15)
N1—N2—C1—Br1	−179.8 (9)	N4—N5—C11—Br2	177.7 (9)
N2—C1—C2—C3	179.7 (15)	N5—C11—C12—C13	−178.5 (15)
Br1—C1—C2—C3	0 (3)	Br2—C11—C12—C13	3 (2)
N2—C1—C2—C7	−2.0 (16)	N5—C11—C12—C17	0.7 (15)
Br1—C1—C2—C7	178.0 (10)	Br2—C11—C12—C17	−177.3 (10)
C1—C2—C3—C4	179.1 (16)	C17—C12—C13—C14	2 (2)
C7—C2—C3—C4	1.1 (19)	C11—C12—C13—C14	−178.6 (14)
C2—C3—C4—C5	0 (2)	C12—C13—C14—C15	−1 (2)
C3—C4—C5—C6	1 (2)	C13—C14—C15—C16	−1 (2)
C3—C4—C5—N3	−179.5 (12)	C13—C14—C15—N6	179.5 (12)
O2—N3—C5—C6	−173.3 (12)	O3—N6—C15—C16	−0.3 (18)
O1—N3—C5—C6	6.5 (17)	O4—N6—C15—C16	−180.0 (13)
O2—N3—C5—C4	6.8 (18)	O3—N6—C15—C14	179.4 (12)
O1—N3—C5—C4	−173.4 (12)	O4—N6—C15—C14	−0.2 (18)
C4—C5—C6—C7	−1.2 (18)	C14—C15—C16—C17	2 (2)
N3—C5—C6—C7	178.9 (10)	N6—C15—C16—C17	−178.6 (11)
N2—N1—C7—C2	−3.0 (13)	N5—N4—C17—C16	−179.5 (14)
C8—N1—C7—C2	−172.0 (12)	C18—N4—C17—C16	−4 (2)
N2—N1—C7—C6	−179.2 (12)	N5—N4—C17—C12	0.6 (15)
C8—N1—C7—C6	12 (2)	C18—N4—C17—C12	175.6 (13)
C3—C2—C7—N1	−178.4 (11)	C15—C16—C17—N4	179.5 (13)
C1—C2—C7—N1	2.9 (13)	C15—C16—C17—C12	−1 (2)
C3—C2—C7—C6	−1.8 (18)	C13—C12—C17—N4	178.6 (12)
C1—C2—C7—C6	179.5 (12)	C11—C12—C17—N4	−0.8 (14)
C5—C6—C7—N1	177.5 (12)	C13—C12—C17—C16	−1 (2)
C5—C6—C7—C2	1.8 (17)	C11—C12—C17—C16	179.3 (13)
N2—N1—C8—C9	−77.9 (15)	N5—N4—C18—C19	−71.9 (15)
C7—N1—C8—C9	90.1 (14)	C17—N4—C18—C19	113.4 (15)
N1—C8—C9—C10	−125.4 (16)	N4—C18—C19—C20	116.0 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1ⁱ	0.95	2.46	3.304 (16)	147
C18—H18B···O4ⁱⁱ	0.99	2.59	3.578 (16)	174
C9—H9···Br1ⁱⁱⁱ	0.95	3.09	3.814 (11)	134
C18—H18A···Br1^iv	0.99	2.91	3.770 (14)	146

Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z+1; (iv) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The support of NSF-MRI Grant No. 1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

Abbassi, N., Rakib, E. M., Chicha, H., Bouissane, L., Hannioui, A., Aiello, C., Gangemi, R., Castagnola, P., Rosano, C. & Viale, M. (2014). Arch. Pharm. Chem. Life Sci. 347, 423–431. Web of Science CrossRef CAS Google Scholar
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Mohamed Abdelahi, M. M., El Bakri, Y., Benchidmi, M., Essassi, E. M. & &Mague, J. T. (2017). IUCrData, 2, x170432. Google Scholar
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Sheldrick, G. M. (2009). TWINABS. University of Göttingen, Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

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IUCrDATA

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Volume 3| Part 1| January 2018| x171837

https://doi.org/10.1107/S2414314617018375

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds