1-Benzyl-5-nitro-1H-indazole

Boulhaoua, M.; Abdelahi, M.M.; Benchidmi, M.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314616004855

organic compounds

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ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160485

doi:10.1107/S2414314616004855

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1-Benzyl-5-nitro-1H-indazole

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

^aLaboratoire de Chimie Organique Hétérocyclique, 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: mboulhaoua@gmail.com

Edited by J. Simpson, University of Otago, New Zealand (Received 16 March 2016; accepted 22 March 2016; online 31 March 2016)

The asymmetric unit of the title compound, C₁₄H₁₁N₃O₂, contains two independent molecules linked by a C—H⋯O hydrogen bond. Pairs of neighboring dimeric units associate via π–π stacking interactions.

Keywords: crystal structure; indazole derivatives; C—H⋯O hydrogen bond.

CCDC reference: 1470135

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Chemical scheme

Structure description

Indazole derivatives are a versatile class of compounds that have found use in biology, catalysis, and medicinal chemistry (Schmidt et al., 2008 ). Although rare in nature (Liu et al., 2004 ; Ali et al., 2008 ), indazoles exhibit a variety of biological activities such as HIV protease inhibition (Patel et al., 1999 ), antiarrhythmic and analgesic activities (Mosti et al., 2000 ), and antitumor activity and antihypertensive properties (Bouissane et al., 2006 ; Abbassi et al., 2012 ). As a continuation of our studies of indazole derivatives (Boulhaoua et al., 2015 ) we report the synthesis and structure of the title compound.

The asymmetric unit contains two independent molecules which have slightly different orientations of the pendant phenyl groups. Thus, the C9–C14 ring in molecule 1 (Fig. 1) makes a dihedral angle of 79.26 (3)° with the mean plane of its indazole moiety while the corresponding angle in molecule 2 is 75.55 (4)°. In both molecules, the nitro groups are very slightly twisted out of the planes of the indazole ring systems. A weak C20—H20⋯O2 hydrogen bond links the two unique molecules in the asymmetric unit (Fig. 1, Table 1). π–π-stacking interactions occur between the C2–C7 benzene rings and the C16–C21 rings of the indazole ring systems of related molecules, Fig. 2, with Cg1⋯Cg6ⁱ and Cg1ⁱⁱ⋯Cg6 distances of 3.5257 (7) Å [symmetry codes: (i) $[{3\over 2}]$ − x, − $[{1\over 2}]$ + y, $[{3\over 2}]$ − z; (ii) $[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z]. These contacts form tetramers which pack without other short contacts (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20⋯O2	0.95	2.48	3.2242 (17)	135

Figure 1
The title molecule with the atom- labeling scheme and 50% probability ellipsoids. The intermolecular C—H⋯O hydrogen bond is shown as a dotted line.

Figure 2
Detail of the π-stacking [symmetry code: (i) $[{3\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z].

Figure 3
Packing viewed along the b axis with the intermolecular C—H⋯O hydrogen bonds shown as dotted lines.

Synthesis and crystallization

5-Nitro-1H-indazole (0.5 g, 3 mmol) and benzyl chloride (0.7 ml, 6 mmol) were reacted in THF (20 ml) in the presence of potassium carbonate (0.83 g, 6 mmol) and tetra-n-butylammonium bromide (0.11 g, 0.33 mmol). The mixture was stirred for 48 h, filtered, and the THF removed under vacuum. The product was separated by chromatography on silica gel with a hexane:ethyl acetate (8:2) solvent system. Crystals were obtained when the solvent was allowed to evaporate. The solid product was purified by recrystallization from ethyl acetate to afford colourless crystals (yield: 58%; m.p. = 393–395 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₂
M_r	253.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	14.0236 (3), 6.9976 (1), 25.3551 (5)
β (°)	105.245 (1)
V (Å³)	2400.58 (8)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.80
Crystal size (mm)	0.24 × 0.13 × 0.05

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.86, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	18022, 4833, 3995
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.04
No. of reflections	4833
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1470135

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616004855/sj4014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004855/sj4014Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616004855/sj4014Isup3.cdx

Supporting information file. DOI: 10.1107/S2414314616004855/sj4014Isup4.cml

checkCIF report

Experimental top

Structure description top

Indazole derivatives are a versatile class of compounds that have found use in biology, catalysis, and medicinal chemistry (Schmidt et al., 2008). Although rare in nature (Liu et al., 2004; Ali et al., 2008), indazoles exhibit a variety of biological activities such as HIV protease inhibition (Patel et al., 1999), antiarrhythmic and analgesic activities (Mosti et al., 2000), and antitumor activity and antihypertensive properties (Bouissane et al., 2006; Abbassi et al., 2012). As a continuation of our studies of indazole derivatives (Boulhaoua et al., 2015) we report the synthesis and structure of the title compound.

The asymmetric unit contains two independent molecules which have slightly different orientations of the pendant phenyl groups. Thus, the C9–C14 ring in molecule 1 (Fig. 1) makes a dihedral angle of 79.26 (3)° with the mean plane of its indazole moiety while the corresponding angle in molecule 2 is 75.55 (4)°. In both molecules, the nitro groups are very slightly twisted out of the planes of the indazole ring systems. A weak C20—H20···O2 hydrogen bond links the two unique molecules in the asymmetric unit (Fig. 1, Table 1). π–π-stacking interactions occur between the C2–C7 benzene rings and the C16–C21 rings of the indazole ring systems of related molecules, Fig 2, with Cg1···Cg6ⁱ and Cg1ⁱⁱ···Cg6 distances of 3.5257 (7) Å [symmetry codes: (i) 3/2 − x, −1/2 + y, 3/2 − z; (ii) 3/2 − x, 1/2 + y, 3/2 − z]. These contacts form tetramers which pack without other short contacts (Fig. 3).

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: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with the atom- labeling scheme and 50% probability ellipsoids. The intermolecular C—H···O hydrogen bond is shown as a dotted line.
	Fig. 2. Detail of the π-stacking [symmetry code: (i) 3/2 − x, 1/2 + y, 3/2 − z].
	Fig. 3. Packing viewed along the b axis with the intermolecular C—H···O hydrogen bonds shown as dotted lines.

1-Benzyl-5-nitro-1H-indazole top

Crystal data top

C₁₄H₁₁N₃O₂	F(000) = 1056
M_r = 253.26	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 14.0236 (3) Å	Cell parameters from 9935 reflections
b = 6.9976 (1) Å	θ = 3.3–74.4°
c = 25.3551 (5) Å	µ = 0.80 mm⁻¹
β = 105.245 (1)°	T = 150 K
V = 2400.58 (8) Å³	Thick plate, colourless
Z = 8	0.24 × 0.13 × 0.05 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4833 independent reflections
Radiation source: INCOATEC IµS micro–focus source	3995 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.038
Detector resolution: 10.4167 pixels mm^-1	θ_max = 74.6°, θ_min = 3.3°
ω scans	h = −16→17
Absorption correction: multi-scan (SADABS; Bruker, 2016)	k = −8→8
T_min = 0.86, T_max = 0.96	l = −31→30
18022 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0462P)² + 0.4746P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4833 reflections	Δρ_max = 0.23 e Å⁻³
344 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015a), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00186 (16)

Crystal data top

C₁₄H₁₁N₃O₂	V = 2400.58 (8) Å³
M_r = 253.26	Z = 8
Monoclinic, P2₁/n	Cu Kα radiation
a = 14.0236 (3) Å	µ = 0.80 mm⁻¹
b = 6.9976 (1) Å	T = 150 K
c = 25.3551 (5) Å	0.24 × 0.13 × 0.05 mm
β = 105.245 (1)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	4833 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2016)	3995 reflections with I > 2σ(I)
T_min = 0.86, T_max = 0.96	R_int = 0.038
18022 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
4833 reflections	Δρ_min = −0.16 e Å⁻³
344 parameters

Special details top

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.

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 > σ(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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 − 0.99 Å) and included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
O1	0.58982 (9)	0.48868 (18)	0.69442 (5)	0.0515 (3)
O2	0.74164 (10)	0.54713 (19)	0.73731 (4)	0.0536 (3)
N1	0.81889 (8)	0.27863 (14)	0.52227 (4)	0.0249 (2)
N2	0.91894 (8)	0.29139 (15)	0.54421 (5)	0.0293 (2)
N3	0.67906 (10)	0.48846 (17)	0.69708 (5)	0.0381 (3)
C1	0.93186 (9)	0.33746 (18)	0.59595 (5)	0.0287 (3)
H1	0.9946	0.3544	0.6213	0.034*
C2	0.84003 (9)	0.35852 (17)	0.60908 (5)	0.0248 (3)
C3	0.81071 (10)	0.41041 (18)	0.65552 (5)	0.0286 (3)
H3	0.8575	0.4376	0.6892	0.034*
C4	0.71084 (10)	0.42037 (18)	0.65016 (5)	0.0295 (3)
C5	0.63849 (10)	0.37740 (18)	0.60129 (6)	0.0294 (3)
H5	0.5704	0.3836	0.6003	0.035*
C6	0.66655 (9)	0.32670 (18)	0.55531 (5)	0.0265 (3)
H6	0.6192	0.2975	0.5220	0.032*
C7	0.76849 (9)	0.31984 (16)	0.55972 (5)	0.0233 (3)
C8	0.77899 (10)	0.24803 (18)	0.46378 (5)	0.0287 (3)
H8A	0.7174	0.1721	0.4574	0.034*
H8B	0.8271	0.1741	0.4496	0.034*
C9	0.75716 (9)	0.43506 (18)	0.43307 (5)	0.0261 (3)
C10	0.83424 (9)	0.56089 (18)	0.43277 (5)	0.0270 (3)
H10	0.9003	0.5261	0.4506	0.032*
C11	0.81532 (10)	0.73627 (19)	0.40663 (5)	0.0301 (3)
H11	0.8682	0.8217	0.4071	0.036*
C12	0.71933 (11)	0.7866 (2)	0.37989 (6)	0.0368 (3)
H12	0.7062	0.9063	0.3618	0.044*
C13	0.64270 (11)	0.6621 (2)	0.37965 (6)	0.0429 (4)
H13	0.5768	0.6965	0.3612	0.051*
C14	0.66151 (10)	0.4867 (2)	0.40624 (6)	0.0359 (3)
H14	0.6084	0.4021	0.4060	0.043*
O3	0.96938 (8)	0.32608 (19)	0.92541 (6)	0.0556 (3)
O4	0.93680 (8)	0.2992 (2)	1.00357 (5)	0.0600 (4)
N4	0.51068 (8)	0.37236 (15)	0.85992 (4)	0.0286 (2)
N5	0.47236 (8)	0.33620 (16)	0.90328 (5)	0.0308 (3)
N6	0.91111 (9)	0.32284 (18)	0.95410 (6)	0.0402 (3)
C15	0.54843 (10)	0.31492 (18)	0.94615 (5)	0.0281 (3)
H15	0.5433	0.2907	0.9822	0.034*
C16	0.63952 (9)	0.33289 (17)	0.93161 (5)	0.0246 (3)
C17	0.73991 (10)	0.31849 (17)	0.95871 (5)	0.0272 (3)
H17	0.7617	0.2919	0.9967	0.033*
C18	0.80552 (9)	0.34486 (18)	0.92748 (6)	0.0292 (3)
C19	0.77729 (10)	0.38914 (19)	0.87135 (6)	0.0316 (3)
H19	0.8263	0.4096	0.8522	0.038*
C20	0.67933 (10)	0.40277 (18)	0.84434 (5)	0.0300 (3)
H20	0.6585	0.4324	0.8065	0.036*
C21	0.61093 (9)	0.37104 (17)	0.87506 (5)	0.0260 (3)
C22	0.44581 (11)	0.3748 (2)	0.80465 (6)	0.0360 (3)
H22A	0.4753	0.4575	0.7815	0.043*
H22B	0.3815	0.4311	0.8055	0.043*
C23	0.42832 (10)	0.17754 (19)	0.77920 (5)	0.0310 (3)
C24	0.35930 (10)	0.0558 (2)	0.79196 (6)	0.0345 (3)
H24	0.3238	0.0954	0.8172	0.041*
C25	0.34200 (12)	−0.1238 (2)	0.76785 (6)	0.0398 (3)
H25	0.2946	−0.2063	0.7766	0.048*
C26	0.39368 (12)	−0.1827 (2)	0.73113 (6)	0.0421 (4)
H26	0.3810	−0.3047	0.7143	0.050*
C27	0.46371 (12)	−0.0641 (2)	0.71898 (6)	0.0418 (4)
H27	0.5000	−0.1051	0.6942	0.050*
C28	0.48104 (11)	0.1157 (2)	0.74309 (6)	0.0363 (3)
H28	0.5294	0.1969	0.7348	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0513 (7)	0.0579 (7)	0.0567 (7)	−0.0026 (5)	0.0343 (6)	−0.0042 (6)
O2	0.0676 (8)	0.0640 (8)	0.0344 (6)	−0.0176 (6)	0.0224 (6)	−0.0121 (5)
N1	0.0232 (5)	0.0240 (5)	0.0279 (5)	−0.0002 (4)	0.0075 (4)	0.0024 (4)
N2	0.0224 (5)	0.0277 (5)	0.0378 (6)	−0.0004 (4)	0.0080 (5)	0.0032 (5)
N3	0.0503 (8)	0.0343 (6)	0.0366 (7)	−0.0063 (5)	0.0238 (6)	0.0004 (5)
C1	0.0226 (6)	0.0277 (6)	0.0338 (7)	−0.0020 (5)	0.0039 (5)	0.0028 (5)
C2	0.0247 (6)	0.0209 (6)	0.0274 (6)	−0.0025 (4)	0.0042 (5)	0.0030 (5)
C3	0.0343 (7)	0.0246 (6)	0.0261 (6)	−0.0056 (5)	0.0065 (5)	0.0022 (5)
C4	0.0385 (7)	0.0242 (6)	0.0300 (7)	−0.0034 (5)	0.0164 (6)	0.0018 (5)
C5	0.0263 (6)	0.0270 (6)	0.0372 (7)	−0.0006 (5)	0.0126 (5)	0.0040 (5)
C6	0.0240 (6)	0.0249 (6)	0.0297 (6)	−0.0013 (5)	0.0054 (5)	0.0026 (5)
C7	0.0254 (6)	0.0187 (5)	0.0261 (6)	−0.0020 (4)	0.0075 (5)	0.0022 (4)
C8	0.0321 (7)	0.0259 (6)	0.0288 (7)	−0.0039 (5)	0.0092 (5)	−0.0042 (5)
C9	0.0297 (7)	0.0291 (6)	0.0200 (6)	−0.0030 (5)	0.0075 (5)	−0.0030 (5)
C10	0.0239 (6)	0.0292 (6)	0.0285 (6)	−0.0003 (5)	0.0078 (5)	−0.0004 (5)
C11	0.0304 (7)	0.0312 (7)	0.0305 (7)	−0.0020 (5)	0.0109 (5)	0.0003 (5)
C12	0.0370 (8)	0.0409 (8)	0.0320 (7)	0.0050 (6)	0.0084 (6)	0.0120 (6)
C13	0.0275 (7)	0.0596 (10)	0.0376 (8)	0.0016 (7)	0.0018 (6)	0.0170 (7)
C14	0.0271 (7)	0.0485 (8)	0.0305 (7)	−0.0085 (6)	0.0047 (5)	0.0051 (6)
O3	0.0311 (6)	0.0636 (8)	0.0774 (9)	0.0013 (5)	0.0236 (6)	−0.0142 (6)
O4	0.0315 (6)	0.0854 (10)	0.0555 (8)	0.0031 (6)	−0.0023 (5)	0.0078 (7)
N4	0.0280 (6)	0.0264 (5)	0.0293 (6)	−0.0007 (4)	0.0039 (4)	0.0017 (4)
N5	0.0281 (6)	0.0279 (5)	0.0370 (6)	−0.0003 (4)	0.0099 (5)	0.0001 (5)
N6	0.0264 (6)	0.0357 (6)	0.0585 (9)	0.0013 (5)	0.0111 (6)	−0.0073 (6)
C15	0.0301 (7)	0.0243 (6)	0.0309 (6)	−0.0009 (5)	0.0098 (5)	−0.0003 (5)
C16	0.0271 (6)	0.0188 (5)	0.0279 (6)	0.0000 (5)	0.0073 (5)	−0.0020 (5)
C17	0.0281 (7)	0.0209 (6)	0.0311 (6)	−0.0002 (5)	0.0054 (5)	−0.0020 (5)
C18	0.0252 (7)	0.0223 (6)	0.0396 (7)	0.0008 (5)	0.0077 (5)	−0.0053 (5)
C19	0.0356 (7)	0.0250 (6)	0.0392 (7)	−0.0018 (5)	0.0188 (6)	−0.0056 (5)
C20	0.0388 (7)	0.0250 (6)	0.0284 (6)	−0.0020 (5)	0.0124 (6)	−0.0020 (5)
C21	0.0294 (7)	0.0183 (6)	0.0295 (6)	0.0000 (5)	0.0067 (5)	−0.0014 (5)
C22	0.0362 (8)	0.0295 (7)	0.0348 (7)	0.0020 (5)	−0.0041 (6)	0.0060 (6)
C23	0.0304 (7)	0.0291 (6)	0.0266 (6)	0.0024 (5)	−0.0047 (5)	0.0059 (5)
C24	0.0338 (7)	0.0357 (7)	0.0297 (7)	−0.0007 (6)	0.0006 (5)	0.0038 (6)
C25	0.0442 (8)	0.0353 (7)	0.0328 (7)	−0.0083 (6)	−0.0026 (6)	0.0058 (6)
C26	0.0541 (10)	0.0317 (7)	0.0304 (7)	0.0029 (6)	−0.0064 (6)	0.0015 (6)
C27	0.0451 (9)	0.0446 (8)	0.0313 (7)	0.0097 (7)	0.0024 (6)	0.0011 (6)
C28	0.0340 (7)	0.0402 (8)	0.0302 (7)	−0.0002 (6)	0.0005 (6)	0.0071 (6)

Geometric parameters (Å, º) top

O1—N3	1.2355 (17)	O3—N6	1.2289 (17)
O2—N3	1.2283 (17)	O4—N6	1.2218 (18)
N1—C7	1.3555 (16)	N4—C21	1.3566 (17)
N1—N2	1.3696 (15)	N4—N5	1.3683 (16)
N1—C8	1.4566 (16)	N4—C22	1.4564 (17)
N2—C1	1.3163 (17)	N5—C15	1.3159 (17)
N3—C4	1.4560 (17)	N6—C18	1.4650 (18)
C1—C2	1.4198 (18)	C15—C16	1.4252 (18)
C1—H1	0.9500	C15—H15	0.9500
C2—C3	1.3937 (18)	C16—C17	1.3985 (18)
C2—C7	1.4091 (17)	C16—C21	1.4089 (18)
C3—C4	1.3728 (19)	C17—C18	1.3750 (19)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.4121 (19)	C18—C19	1.408 (2)
C5—C6	1.3716 (19)	C19—C20	1.368 (2)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.4052 (18)	C20—C21	1.4033 (18)
C6—H6	0.9500	C20—H20	0.9500
C8—C9	1.5125 (18)	C22—C23	1.5159 (19)
C8—H8A	0.9900	C22—H22A	0.9900
C8—H8B	0.9900	C22—H22B	0.9900
C9—C14	1.3830 (19)	C23—C28	1.388 (2)
C9—C10	1.3958 (18)	C23—C24	1.390 (2)
C10—C11	1.3868 (18)	C24—C25	1.391 (2)
C10—H10	0.9500	C24—H24	0.9500
C11—C12	1.384 (2)	C25—C26	1.384 (2)
C11—H11	0.9500	C25—H25	0.9500
C12—C13	1.382 (2)	C26—C27	1.381 (2)
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.392 (2)	C27—C28	1.392 (2)
C13—H13	0.9500	C27—H27	0.9500
C14—H14	0.9500	C28—H28	0.9500

C7—N1—N2	111.63 (10)	C21—N4—N5	111.59 (10)
C7—N1—C8	127.81 (11)	C21—N4—C22	127.67 (12)
N2—N1—C8	120.10 (10)	N5—N4—C22	119.83 (11)
C1—N2—N1	106.18 (10)	C15—N5—N4	106.28 (11)
O2—N3—O1	122.50 (13)	O4—N6—O3	123.21 (14)
O2—N3—C4	118.86 (13)	O4—N6—C18	118.47 (13)
O1—N3—C4	118.63 (12)	O3—N6—C18	118.31 (14)
N2—C1—C2	111.30 (11)	N5—C15—C16	111.31 (12)
N2—C1—H1	124.3	N5—C15—H15	124.3
C2—C1—H1	124.3	C16—C15—H15	124.3
C3—C2—C7	120.07 (12)	C17—C16—C21	119.61 (12)
C3—C2—C1	135.43 (12)	C17—C16—C15	136.18 (12)
C7—C2—C1	104.46 (11)	C21—C16—C15	104.20 (11)
C4—C3—C2	116.72 (12)	C18—C17—C16	116.55 (12)
C4—C3—H3	121.6	C18—C17—H17	121.7
C2—C3—H3	121.6	C16—C17—H17	121.7
C3—C4—C5	123.71 (12)	C17—C18—C19	123.98 (12)
C3—C4—N3	117.34 (12)	C17—C18—N6	117.97 (12)
C5—C4—N3	118.88 (12)	C19—C18—N6	118.05 (12)
C6—C5—C4	120.03 (12)	C20—C19—C18	119.99 (12)
C6—C5—H5	120.0	C20—C19—H19	120.0
C4—C5—H5	120.0	C18—C19—H19	120.0
C5—C6—C7	117.03 (12)	C19—C20—C21	117.02 (12)
C5—C6—H6	121.5	C19—C20—H20	121.5
C7—C6—H6	121.5	C21—C20—H20	121.5
N1—C7—C6	131.18 (12)	N4—C21—C20	130.58 (12)
N1—C7—C2	106.40 (11)	N4—C21—C16	106.61 (11)
C6—C7—C2	122.41 (12)	C20—C21—C16	122.80 (12)
N1—C8—C9	111.62 (10)	N4—C22—C23	112.91 (10)
N1—C8—H8A	109.3	N4—C22—H22A	109.0
C9—C8—H8A	109.3	C23—C22—H22A	109.0
N1—C8—H8B	109.3	N4—C22—H22B	109.0
C9—C8—H8B	109.3	C23—C22—H22B	109.0
H8A—C8—H8B	108.0	H22A—C22—H22B	107.8
C14—C9—C10	119.00 (12)	C28—C23—C24	119.11 (13)
C14—C9—C8	121.22 (12)	C28—C23—C22	120.65 (13)
C10—C9—C8	119.77 (11)	C24—C23—C22	120.24 (13)
C11—C10—C9	120.65 (12)	C23—C24—C25	120.22 (15)
C11—C10—H10	119.7	C23—C24—H24	119.9
C9—C10—H10	119.7	C25—C24—H24	119.9
C12—C11—C10	119.90 (13)	C26—C25—C24	120.18 (15)
C12—C11—H11	120.1	C26—C25—H25	119.9
C10—C11—H11	120.1	C24—C25—H25	119.9
C13—C12—C11	119.78 (13)	C27—C26—C25	119.99 (14)
C13—C12—H12	120.1	C27—C26—H26	120.0
C11—C12—H12	120.1	C25—C26—H26	120.0
C12—C13—C14	120.37 (13)	C26—C27—C28	119.83 (15)
C12—C13—H13	119.8	C26—C27—H27	120.1
C14—C13—H13	119.8	C28—C27—H27	120.1
C9—C14—C13	120.30 (13)	C23—C28—C27	120.64 (14)
C9—C14—H14	119.9	C23—C28—H28	119.7
C13—C14—H14	119.9	C27—C28—H28	119.7

C7—N1—N2—C1	1.10 (13)	C21—N4—N5—C15	0.97 (14)
C8—N1—N2—C1	173.93 (11)	C22—N4—N5—C15	170.86 (11)
N1—N2—C1—C2	−0.75 (14)	N4—N5—C15—C16	−1.21 (14)
N2—C1—C2—C3	−177.42 (14)	N5—C15—C16—C17	−177.66 (13)
N2—C1—C2—C7	0.16 (14)	N5—C15—C16—C21	1.00 (14)
C7—C2—C3—C4	0.19 (17)	C21—C16—C17—C18	0.53 (17)
C1—C2—C3—C4	177.48 (14)	C15—C16—C17—C18	179.03 (14)
C2—C3—C4—C5	1.41 (19)	C16—C17—C18—C19	1.61 (19)
C2—C3—C4—N3	−175.42 (11)	C16—C17—C18—N6	−177.49 (11)
O2—N3—C4—C3	5.49 (19)	O4—N6—C18—C17	−6.44 (19)
O1—N3—C4—C3	−176.00 (12)	O3—N6—C18—C17	172.42 (13)
O2—N3—C4—C5	−171.50 (13)	O4—N6—C18—C19	174.40 (13)
O1—N3—C4—C5	7.01 (18)	O3—N6—C18—C19	−6.74 (19)
C3—C4—C5—C6	−1.6 (2)	C17—C18—C19—C20	−1.9 (2)
N3—C4—C5—C6	175.15 (12)	N6—C18—C19—C20	177.16 (12)
C4—C5—C6—C7	0.17 (18)	C18—C19—C20—C21	0.04 (18)
N2—N1—C7—C6	179.18 (12)	N5—N4—C21—C20	−179.26 (13)
C8—N1—C7—C6	7.0 (2)	C22—N4—C21—C20	11.8 (2)
N2—N1—C7—C2	−1.00 (13)	N5—N4—C21—C16	−0.34 (13)
C8—N1—C7—C2	−173.14 (11)	C22—N4—C21—C16	−169.25 (12)
C5—C6—C7—N1	−178.80 (12)	C19—C20—C21—N4	−179.15 (12)
C5—C6—C7—C2	1.41 (18)	C19—C20—C21—C16	2.08 (18)
C3—C2—C7—N1	178.54 (11)	C17—C16—C21—N4	178.56 (11)
C1—C2—C7—N1	0.50 (13)	C15—C16—C21—N4	−0.37 (13)
C3—C2—C7—C6	−1.62 (18)	C17—C16—C21—C20	−2.42 (18)
C1—C2—C7—C6	−179.66 (11)	C15—C16—C21—C20	178.65 (12)
C7—N1—C8—C9	80.48 (15)	C21—N4—C22—C23	83.39 (17)
N2—N1—C8—C9	−91.07 (13)	N5—N4—C22—C23	−84.71 (16)
N1—C8—C9—C14	−114.90 (14)	N4—C22—C23—C28	−99.17 (15)
N1—C8—C9—C10	63.43 (15)	N4—C22—C23—C24	80.59 (16)
C14—C9—C10—C11	0.87 (19)	C28—C23—C24—C25	−1.39 (19)
C8—C9—C10—C11	−177.50 (12)	C22—C23—C24—C25	178.84 (12)
C9—C10—C11—C12	−0.9 (2)	C23—C24—C25—C26	0.2 (2)
C10—C11—C12—C13	0.4 (2)	C24—C25—C26—C27	1.0 (2)
C11—C12—C13—C14	0.2 (2)	C25—C26—C27—C28	−1.0 (2)
C10—C9—C14—C13	−0.4 (2)	C24—C23—C28—C27	1.39 (19)
C8—C9—C14—C13	177.99 (13)	C22—C23—C28—C27	−178.85 (12)
C12—C13—C14—C9	−0.2 (2)	C26—C27—C28—C23	−0.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2	0.95	2.48	3.2242 (17)	135

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O2	0.95	2.48	3.2242 (17)	135

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₂
M_r	253.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	14.0236 (3), 6.9976 (1), 25.3551 (5)
β (°)	105.245 (1)
V (Å³)	2400.58 (8)
Z	8
Radiation type	Cu Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.24 × 0.13 × 0.05

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016)
T_min, T_max	0.86, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	18022, 4833, 3995
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.094, 1.04
No. of reflections	4833
No. of parameters	344
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.16

Computer programs: APEX3 (Bruker, 2016), SAINT (Bruker, 2016), SHELXT (Sheldrick, 2015a), SHELXL2014 (Sheldrick, 2015b), DIAMOND (Brandenburg & Putz, 2012), SHELXTL (Sheldrick, 2008).

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., Chicha, H., Rakib, el M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240–249. CrossRef CAS PubMed Google Scholar
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Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
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Patel, M., Rodgers, J. D., McHugh, R. J. Jr, Johnson, B. L., Cordova, B. C., Klabe, R. M., Bacheler, L. T., Erickson-Viitanen, S. & Ko, S. S. (1999). Bioorg. Med. Chem. Lett. 9, 3217–3220. CrossRef PubMed CAS Google Scholar
Schmidt, A., Beutler, A. & Snovydovych, B. (2008). Eur. J. Org. Chem. pp. 4073–4095. Web of Science CrossRef Google Scholar
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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

ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160485

doi:10.1107/S2414314616004855

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

1-Benzyl-5-nitro-1H-indazole

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds