1-Methyl-5-nitro-3-phenyl-1H-indazole

Naas, M.; Benchidmi, M.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S2414314616009615

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160961

doi:10.1107/S2414314616009615

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1-Methyl-5-nitro-3-phenyl-1H-indazole

Mohammed Naas,^a,^b ^* Mohammed Benchidmi,^a El Mokhtar Essassi,^a Mohamed Saadi ^c and Lahcen El Ammari ^c

^aLaboratoire de Chimie Organique Heterocyclique URAC 21, Pôle de Compétences Pharmacochimie Faculté des Sciences, Mohammed V University in Rabat, BP 1014, Avenue Ibn Batouta, Rabat, Morocco, ^bInstitut de Chimie Organique et Analytique (ICOA), Université d'Orleans, UMR CNRS 7311, BP 6759, 45067 Orléans Cedex 2, France, and ^cLaboratoire de Chimie du Solide Appliquée, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: naas_m21@yahoo.com

Edited by J. Simpson, University of Otago, New Zealand (Received 11 June 2016; accepted 14 June 2016; online 24 June 2016)

The title compound, C₁₄H₁₁N₃O₂, crystallizes with two molecules in the asymmetric unit. The indazole ring system and the nitro group are nearly coplanar, with the largest deviations from the mean plane being 0.070 (4) Å in one molecule and 0.022 (3) Å in the second. The dihedral angle between the mean plane through the phenyl ring and the mean plane of the indazole ring system is of 23.24 (18)° in the first molecule and 26.87 (18)° in the second. In the crystal, molecules are linked by two C—H⋯O hydrogen bonds, forming linear zigzag tapes running along the c-axis direction, and by π–π stacking of molecules along the b axis, generating a three-dimensional structure.

Keywords: crystal structure; indazole ring; hydrogen bonds; π–π contacts.

CCDC reference: 1485400

Structure description

3-Substituted indazoles obtained from different cross-coupling reactions are common components of drugs and have been found to be of pharmaceutical interest in a variety of therapeutic areas (Cerecetto et al., 2005 ; Jennings et al., 2007 ; Sun et al., 1997 , Bouissane et al., 2006 ; Naas et al., 2014 ). They frequently comprise the core frame of numerous pharmaceutically active compounds, such as Lonidamine [1-(2,4-dichlorobenzyl)-1H-indazole-3-carboxylic acid] and Granisetron {1-methyl-N-[(1R,3R,5S)-9-methyl-9-azabicyclo[3.3.1]nonan-3-yl]-1H-indazole-3-carboxamide}. The present paper is a continuation of our research work devoted to the development of the indazole derivatives with potential pharmacological activities (El Brahmi et al., 2011 ; El Brahmi et al., 2012 ).

The asymmetric unit of the title compound is built up from two independent molecules with different orientations, Fig. 1. The two fused five- and six-membered ring systems in each molecule are almost planar, with a maximum deviation of 0.018 (4) Å for C7 in the first molecule (N1,N2,N3,O1,O2,C1–C14) and 0.022 (3) Å for C22 in the second (N4,N5,N6,O3,O4,C15–C28). The dihedral angle between the two phenyl rings is 26.1 (2)°. Moreover, the mean plane of the indazole ring system makes a dihedral angle of 23.24 (18)° with the mean plane through the phenyl ring belonging to the first molecule and 26.87 (18)° in the second molecule. A least-squares overlay of the two molecules (Spek, 2009 ) is shown in Fig. 2 and reveals that the principal difference between the two is the relative inclinations of the C1–C6 and C19–C25 phenyl rings with respect to the planes of the indazole ring systems.

Figure 1
The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Figure 2
Least-squares fit of the two molecules in the asymmetric unit (one molecule is inverted).

In the crystal, molecules are linked by C19—H19⋯O4 and C14—H14B⋯O2 hydrogen bonds (Table 1), forming linear, zigzag tapes running along the c-axis direction (Fig. 3). In addition, molecules are linked by five π–π stacking interactions between the fused rings, Fig. 4, with centroid–centroid distances in the range 3.852 (2) to 3.917 (2) Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14B⋯O2ⁱ	0.96	2.51	3.395 (6)	154
C19—H19⋯O4ⁱⁱ	0.93	2.46	3.288 (6)	148
Symmetry codes: (i) x, y, z-1; (ii) $[-x+{\script{1\over 2}}, y, z+{\script{1\over 2}}]$ .

Figure 3
Packing of the title compound viewed along the b-axis direction showing the C—H⋯O hydrogen bonds.

Figure 4
π–π stacking interactions viewed along c. Cg1, Cg3, Cg5 and Cg7 are the centroids of the N1/N2/C7/C8/C13, C8–C13, N4/N5/C21/C22/C27 and C22–C27 rings, respectively, with centroids shown as colored spheres and Cg⋯Cg contacts drawn as green dotted lines.

Synthesis and crystallization

In a 10 ml flask, a solution of phenanthroline (0.048 g, 0.31 mmol) in N,N-dimethylacetamide (DMA) (5 ml) was degassed by bubbling argon through the solution, and then palladium acetate (0.045 g, 0.14 mmol) was added. The solution was stirred at room temperature for 3 min, then K₂CO₃ (0.39 g, 2.1 mmol), 1-methyl-5-nitro-indazole (0.12 g, 0.7 mmol) and iodobenzene (0.18 g, 0.9 mmol) were successively added. The reaction mixture was heated at reflux under argon for 48 h, and then it was allowed to cool. The mixture was filtered through Celite and the DMA phase was extracted three times with ethyl acetate, dried with magnesium sulfate, and concentrated under reduced pressure. The title compound (m.p. = 396 K; yield = 65%) was purified by flash chromatography on silica gel with a petroleum:ethyl acetate (9:1) solvent system and recrystallized from ethanol to afford colourless crystals of a suitable size for the X-ray diffraction study.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The structure was refined as a two-component inversion twin with equal domain ratios.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₁N₃O₂
M_r	253.26
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	33.4769 (17), 7.4977 (3), 9.7916 (4)
V (Å³)	2457.69 (19)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.28 × 0.19

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.638, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	13395, 5245, 3328
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.130, 1.01
No. of reflections	5245
No. of parameters	344
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15
Absolute structure	Refined as an inversion twin.
Absolute structure parameter	2 (2)
Computer programs: APEX2 and SAINT-Plus (Bruker, 2009), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ), PLATON (Spek, 2009) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1485400

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616009615/sj4047sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009615/sj4047Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009615/sj4047Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

1-Methyl-5-nitro-3-phenyl-1H-indazole top

Crystal data top

C₁₄H₁₁N₃O₂	D_x = 1.369 Mg m⁻³
M_r = 253.26	Melting point: 396 K
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
a = 33.4769 (17) Å	Cell parameters from 5245 reflections
b = 7.4977 (3) Å	θ = 2.4–27.1°
c = 9.7916 (4) Å	µ = 0.10 mm⁻¹
V = 2457.69 (19) Å³	T = 296 K
Z = 8	Block, colourless
F(000) = 1056	0.33 × 0.28 × 0.19 mm

Data collection top

Bruker X8 APEX diffractometer	5245 independent reflections
Radiation source: fine-focus sealed tube	3328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
φ and ω scans	θ_max = 27.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −30→42
T_min = 0.638, T_max = 0.746	k = −9→9
13395 measured reflections	l = −12→12

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.049	w = 1/[σ²(F_o²) + (0.0579P)² + 0.091P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.130	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.16 e Å⁻³
5245 reflections	Δρ_min = −0.15 e Å⁻³
344 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: 2 (2)

Special details top

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. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
C1	0.45757 (13)	0.7758 (5)	0.8046 (5)	0.0631 (11)
H1	0.4420	0.7154	0.7410	0.076*
C2	0.49860 (16)	0.7540 (6)	0.8036 (6)	0.0797 (14)
H2	0.5105	0.6813	0.7382	0.096*
C3	0.52212 (14)	0.8402 (7)	0.8998 (6)	0.0784 (14)
H3	0.5497	0.8247	0.8998	0.094*
C4	0.50432 (14)	0.9486 (6)	0.9949 (5)	0.0708 (13)
H4	0.5200	1.0059	1.0599	0.085*
C5	0.46349 (12)	0.9737 (5)	0.9955 (4)	0.0579 (10)
H5	0.4519	1.0488	1.0600	0.069*
C6	0.43943 (12)	0.8867 (5)	0.8996 (4)	0.0488 (9)
C7	0.39618 (12)	0.9148 (5)	0.8928 (4)	0.0477 (9)
C8	0.36860 (11)	0.9732 (4)	0.9954 (4)	0.0461 (9)
C9	0.37031 (13)	1.0185 (4)	1.1343 (4)	0.0494 (9)
H9	0.3942	1.0138	1.1827	0.059*
C10	0.33550 (14)	1.0697 (5)	1.1956 (4)	0.0544 (10)
C11	0.29892 (13)	1.0770 (6)	1.1283 (5)	0.0622 (11)
H11	0.2762	1.1139	1.1751	0.075*
C12	0.29627 (13)	1.0300 (5)	0.9938 (5)	0.0615 (11)
H12	0.2720	1.0332	0.9473	0.074*
C13	0.33147 (11)	0.9771 (5)	0.9290 (4)	0.0496 (9)
C14	0.30967 (14)	0.9067 (6)	0.6881 (4)	0.0697 (13)
H14A	0.2835	0.9377	0.7204	0.105*
H14B	0.3172	0.9860	0.6155	0.105*
H14C	0.3095	0.7862	0.6548	0.105*
C15	0.06659 (14)	0.6121 (5)	0.7116 (5)	0.0586 (11)
H15	0.0443	0.6102	0.6551	0.070*
C16	0.06358 (16)	0.6833 (7)	0.8421 (6)	0.0804 (14)
H16	0.0393	0.7283	0.8727	0.096*
C17	0.09621 (17)	0.6875 (7)	0.9256 (5)	0.0807 (14)
H17	0.0941	0.7362	1.0127	0.097*
C18	0.13218 (16)	0.6199 (6)	0.8814 (4)	0.0709 (13)
H18	0.1544	0.6233	0.9384	0.085*
C19	0.13518 (14)	0.5474 (6)	0.7527 (4)	0.0582 (11)
H19	0.1594	0.5001	0.7240	0.070*
C20	0.10261 (12)	0.5436 (5)	0.6649 (4)	0.0456 (9)
C21	0.10652 (11)	0.4730 (4)	0.5262 (4)	0.0443 (9)
C22	0.14088 (11)	0.4648 (4)	0.4399 (4)	0.0439 (8)
C23	0.18067 (12)	0.5160 (5)	0.4490 (4)	0.0492 (9)
H23	0.1909	0.5688	0.5275	0.059*
C24	0.20434 (13)	0.4850 (5)	0.3366 (5)	0.0598 (11)
C25	0.19033 (17)	0.4081 (6)	0.2148 (5)	0.0700 (13)
H25	0.2077	0.3899	0.1420	0.084*
C26	0.15079 (16)	0.3597 (5)	0.2040 (4)	0.0665 (13)
H26	0.1408	0.3085	0.1245	0.080*
C27	0.12625 (13)	0.3904 (5)	0.3168 (4)	0.0494 (10)
C28	0.05914 (16)	0.2949 (6)	0.2328 (5)	0.0824 (15)
H28A	0.0331	0.2863	0.2733	0.124*
H28B	0.0582	0.3758	0.1569	0.124*
H28C	0.0674	0.1793	0.2017	0.124*
N1	0.37717 (10)	0.8847 (4)	0.7771 (3)	0.0524 (8)
N2	0.33801 (11)	0.9220 (4)	0.7986 (3)	0.0552 (8)
N3	0.33657 (14)	1.1181 (5)	1.3406 (4)	0.0670 (11)
N4	0.07439 (10)	0.4110 (4)	0.4608 (4)	0.0560 (9)
N5	0.08741 (11)	0.3607 (4)	0.3338 (4)	0.0592 (9)
N6	0.24577 (14)	0.5381 (7)	0.3419 (5)	0.0853 (13)
O1	0.36862 (12)	1.1219 (5)	1.4003 (4)	0.0835 (10)
O2	0.30487 (11)	1.1535 (6)	1.3978 (4)	0.0990 (12)
O3	0.25797 (11)	0.6241 (6)	0.4405 (5)	0.1101 (14)
O4	0.26727 (13)	0.4964 (8)	0.2468 (5)	0.146 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.072 (3)	0.055 (2)	0.062 (3)	0.009 (2)	0.010 (2)	−0.001 (2)
C2	0.077 (3)	0.078 (3)	0.084 (4)	0.024 (3)	0.022 (3)	0.000 (3)
C3	0.057 (3)	0.092 (4)	0.086 (4)	0.017 (3)	0.004 (3)	0.026 (3)
C4	0.062 (3)	0.087 (3)	0.063 (3)	0.004 (2)	−0.005 (3)	0.017 (3)
C5	0.060 (3)	0.065 (2)	0.049 (2)	0.007 (2)	−0.001 (2)	0.008 (2)
C6	0.058 (2)	0.047 (2)	0.041 (2)	0.0032 (17)	0.006 (2)	0.0099 (17)
C7	0.057 (2)	0.044 (2)	0.042 (2)	−0.0001 (17)	0.0033 (19)	0.0009 (16)
C8	0.054 (2)	0.0426 (18)	0.041 (2)	−0.0012 (16)	0.003 (2)	0.0037 (17)
C9	0.059 (2)	0.047 (2)	0.042 (2)	−0.0006 (18)	0.0006 (19)	0.0036 (17)
C10	0.067 (3)	0.054 (2)	0.042 (2)	0.0024 (19)	0.008 (2)	0.0028 (17)
C11	0.056 (3)	0.069 (3)	0.061 (3)	0.001 (2)	0.012 (2)	0.001 (2)
C12	0.053 (2)	0.068 (2)	0.064 (3)	−0.003 (2)	−0.003 (2)	0.002 (2)
C13	0.054 (2)	0.049 (2)	0.046 (2)	−0.0069 (17)	−0.001 (2)	0.0020 (18)
C14	0.080 (3)	0.077 (3)	0.052 (3)	−0.010 (2)	−0.017 (2)	−0.002 (2)
C15	0.056 (3)	0.057 (2)	0.063 (3)	0.000 (2)	0.011 (2)	−0.001 (2)
C16	0.072 (3)	0.087 (3)	0.082 (4)	0.006 (3)	0.030 (3)	−0.018 (3)
C17	0.105 (4)	0.090 (3)	0.047 (3)	−0.009 (3)	0.015 (3)	−0.016 (3)
C18	0.085 (4)	0.090 (3)	0.038 (2)	−0.001 (3)	0.000 (2)	−0.005 (2)
C19	0.063 (3)	0.071 (3)	0.041 (2)	0.010 (2)	0.001 (2)	0.0004 (19)
C20	0.052 (2)	0.0429 (19)	0.042 (2)	−0.0002 (16)	0.006 (2)	0.0039 (16)
C21	0.052 (2)	0.0399 (18)	0.041 (2)	0.0009 (16)	−0.0065 (18)	0.0026 (15)
C22	0.054 (2)	0.0421 (18)	0.035 (2)	0.0053 (16)	−0.0066 (19)	0.0015 (15)
C23	0.057 (2)	0.049 (2)	0.042 (2)	0.0047 (16)	−0.0013 (19)	0.0030 (16)
C24	0.061 (3)	0.066 (2)	0.052 (3)	0.011 (2)	0.014 (2)	0.011 (2)
C25	0.096 (4)	0.070 (3)	0.043 (3)	0.021 (3)	0.018 (3)	0.002 (2)
C26	0.106 (4)	0.057 (2)	0.036 (2)	0.012 (2)	−0.006 (2)	−0.0059 (18)
C27	0.070 (3)	0.0414 (19)	0.036 (2)	0.0057 (18)	−0.006 (2)	−0.0012 (16)
C28	0.108 (4)	0.074 (3)	0.065 (3)	−0.016 (3)	−0.044 (3)	−0.003 (2)
N1	0.062 (2)	0.0530 (18)	0.0421 (19)	−0.0014 (15)	−0.0003 (18)	−0.0007 (15)
N2	0.063 (2)	0.0578 (19)	0.045 (2)	0.0003 (16)	−0.0072 (18)	−0.0026 (16)
N3	0.086 (3)	0.068 (2)	0.047 (2)	0.008 (2)	0.021 (2)	0.0023 (17)
N4	0.060 (2)	0.0533 (18)	0.055 (2)	−0.0053 (15)	−0.0106 (18)	0.0037 (16)
N5	0.073 (2)	0.0562 (19)	0.049 (2)	−0.0065 (16)	−0.0162 (19)	−0.0033 (16)
N6	0.064 (3)	0.122 (4)	0.070 (3)	0.014 (3)	0.010 (3)	0.023 (3)
O1	0.091 (3)	0.110 (3)	0.0498 (19)	0.006 (2)	−0.004 (2)	−0.0117 (18)
O2	0.095 (3)	0.143 (3)	0.059 (2)	0.021 (2)	0.029 (2)	−0.001 (2)
O3	0.064 (2)	0.154 (4)	0.113 (4)	−0.018 (2)	0.008 (2)	−0.001 (3)
O4	0.085 (3)	0.253 (6)	0.099 (3)	0.024 (3)	0.044 (3)	0.004 (4)

Geometric parameters (Å, º) top

C1—C2	1.383 (6)	C16—C17	1.365 (7)
C1—C6	1.388 (5)	C16—H16	0.9300
C1—H1	0.9300	C17—C18	1.376 (7)
C2—C3	1.388 (8)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.377 (6)
C3—C4	1.372 (7)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.389 (6)
C4—C5	1.380 (6)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.463 (5)
C5—C6	1.399 (6)	C21—N4	1.336 (5)
C5—H5	0.9300	C21—C22	1.429 (5)
C6—C7	1.465 (5)	C22—C23	1.389 (5)
C7—N1	1.319 (5)	C22—C27	1.416 (5)
C7—C8	1.433 (5)	C23—C24	1.376 (6)
C8—C13	1.403 (5)	C23—H23	0.9300
C8—C9	1.403 (6)	C24—C25	1.404 (7)
C9—C10	1.366 (6)	C24—N6	1.444 (6)
C9—H9	0.9300	C25—C26	1.377 (6)
C10—C11	1.391 (6)	C25—H25	0.9300
C10—N3	1.466 (5)	C26—C27	1.396 (6)
C11—C12	1.367 (7)	C26—H26	0.9300
C11—H11	0.9300	C27—N5	1.330 (5)
C12—C13	1.396 (6)	C28—N5	1.455 (5)
C12—H12	0.9300	C28—H28A	0.9600
C13—N2	1.359 (5)	C28—H28B	0.9600
C14—N2	1.444 (5)	C28—H28C	0.9600
C14—H14A	0.9600	N1—N2	1.357 (4)
C14—H14B	0.9600	N3—O1	1.222 (5)
C14—H14C	0.9600	N3—O2	1.229 (4)
C15—C16	1.388 (7)	N4—N5	1.371 (5)
C15—C20	1.388 (6)	N6—O4	1.218 (6)
C15—H15	0.9300	N6—O3	1.231 (6)

C2—C1—C6	120.7 (4)	C16—C17—H17	119.9
C2—C1—H1	119.7	C18—C17—H17	119.9
C6—C1—H1	119.7	C17—C18—C19	119.8 (5)
C1—C2—C3	120.2 (5)	C17—C18—H18	120.1
C1—C2—H2	119.9	C19—C18—H18	120.1
C3—C2—H2	119.9	C18—C19—C20	121.2 (4)
C4—C3—C2	119.4 (4)	C18—C19—H19	119.4
C4—C3—H3	120.3	C20—C19—H19	119.4
C2—C3—H3	120.3	C15—C20—C19	118.0 (4)
C3—C4—C5	121.0 (5)	C15—C20—C21	121.2 (4)
C3—C4—H4	119.5	C19—C20—C21	120.8 (4)
C5—C4—H4	119.5	N4—C21—C22	110.5 (3)
C4—C5—C6	120.2 (4)	N4—C21—C20	120.0 (4)
C4—C5—H5	119.9	C22—C21—C20	129.5 (4)
C6—C5—H5	119.9	C23—C22—C27	119.6 (4)
C1—C6—C5	118.5 (4)	C23—C22—C21	136.3 (3)
C1—C6—C7	119.2 (4)	C27—C22—C21	104.0 (3)
C5—C6—C7	122.2 (3)	C24—C23—C22	117.1 (4)
N1—C7—C8	110.1 (3)	C24—C23—H23	121.5
N1—C7—C6	119.4 (3)	C22—C23—H23	121.5
C8—C7—C6	130.5 (4)	C23—C24—C25	123.8 (4)
C13—C8—C9	118.7 (4)	C23—C24—N6	118.5 (4)
C13—C8—C7	104.6 (3)	C25—C24—N6	117.7 (4)
C9—C8—C7	136.6 (4)	C26—C25—C24	119.7 (4)
C10—C9—C8	117.3 (4)	C26—C25—H25	120.2
C10—C9—H9	121.3	C24—C25—H25	120.2
C8—C9—H9	121.3	C25—C26—C27	117.5 (4)
C9—C10—C11	123.6 (4)	C25—C26—H26	121.3
C9—C10—N3	118.3 (4)	C27—C26—H26	121.3
C11—C10—N3	118.0 (4)	N5—C27—C26	130.3 (4)
C12—C11—C10	120.2 (4)	N5—C27—C22	107.3 (3)
C12—C11—H11	119.9	C26—C27—C22	122.4 (4)
C10—C11—H11	119.9	N5—C28—H28A	109.5
C11—C12—C13	117.2 (4)	N5—C28—H28B	109.5
C11—C12—H12	121.4	H28A—C28—H28B	109.5
C13—C12—H12	121.4	N5—C28—H28C	109.5
N2—C13—C12	130.5 (4)	H28A—C28—H28C	109.5
N2—C13—C8	106.6 (4)	H28B—C28—H28C	109.5
C12—C13—C8	122.9 (4)	C7—N1—N2	107.3 (3)
N2—C14—H14A	109.5	N1—N2—C13	111.4 (3)
N2—C14—H14B	109.5	N1—N2—C14	120.1 (3)
H14A—C14—H14B	109.5	C13—N2—C14	128.5 (4)
N2—C14—H14C	109.5	O1—N3—O2	122.4 (4)
H14A—C14—H14C	109.5	O1—N3—C10	119.4 (4)
H14B—C14—H14C	109.5	O2—N3—C10	118.3 (5)
C16—C15—C20	120.6 (5)	C21—N4—N5	106.0 (3)
C16—C15—H15	119.7	C27—N5—N4	112.2 (3)
C20—C15—H15	119.7	C27—N5—C28	127.5 (4)
C17—C16—C15	120.2 (5)	N4—N5—C28	120.2 (4)
C17—C16—H16	119.9	O4—N6—O3	122.6 (5)
C15—C16—H16	119.9	O4—N6—C24	118.0 (6)
C16—C17—C18	120.2 (4)	O3—N6—C24	119.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14B···O2ⁱ	0.96	2.51	3.395 (6)	154
C19—H19···O4ⁱⁱ	0.93	2.46	3.288 (6)	148

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and Mohammed V University, Rabat for financial support.

References

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Volume 1| Part 6| June 2016| x160961

doi:10.1107/S2414314616009615

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

1-Methyl-5-nitro-3-phenyl-1H-indazole

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds