2-(2H-Indazol-2-yl)-1-phenyl­ethanone

Özden Özel Güven; Gökhan Türk; Philip D F Adler; Simon J Coles; Tuncer Hökelek

doi:10.1107/S1600536812051811

. 2013 Jan 4;69(Pt 2):o184. doi: 10.1107/S1600536812051811

2-(2H-Indazol-2-yl)-1-phenylethanone

Özden Özel Güven ^a, Gökhan Türk ^a, Philip D F Adler ^b, Simon J Coles ^b, Tuncer Hökelek ^c,^*

PMCID: PMC3569246 PMID: 23424469

Abstract

The asymmetric unit of the title compound, C₁₅H₁₂N₂O, contains two independent molecules with different conformations, the phenyl ring and indazole mean plane in the two molecules forming dihedral angles of 50.82 (5) and 89.29 (6)°. In the crystal, weak C—H⋯O and C–H⋯N hydrogen bonds and C—H⋯π interactions consolidate the packing.

Related literature

For general background to the biological activity of indazole derivatives, see: Lebouvier et al. (2007 ▶); Maggio et al. (2011 ▶); Park et al. (2007 ▶); Plescia et al. (2010 ▶); Raffa et al. (2009 ▶). For related structures, see: Gerpe et al. (2007 ▶); Özel Güven et al. (2008a ▶,b ▶); Raffa et al. (2009 ▶). graphic file with name e-69-0o184-scheme1.jpg

Experimental

Crystal data

C₁₅H₁₂N₂O
M _r = 236.27
Monoclinic,
a = 9.4408 (3) Å
b = 17.9636 (5) Å
c = 13.9415 (4) Å
β = 99.247 (4)°
V = 2333.62 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Saturn724+ diffractometer
23377 measured reflections
5349 independent reflections
3346 reflections with I > 2σ(I)
R _int = 0.084
3 standard reflections every 2 min intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.129
S = 1.02
5349 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Click here for additional data file.^{(24.4KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051811/cv5372sup1.cif

e-69-0o184-sup1.cif^{(24.4KB, cif)}

Click here for additional data file.^{(256.6KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051811/cv5372Isup2.hkl

e-69-0o184-Isup2.hkl^{(256.6KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the N1A/N2A/C9A/C10A/C15A and C10B–C15B rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6A⋯O1B ⁱ	0.93	2.53	3.418 (2)	159
C8A—H81⋯N2A ⁱⁱ	0.97	2.57	3.519 (3)	164
C8A—H82⋯O1B ⁱⁱⁱ	0.97	2.41	3.176 (2)	135
C9B—H9B⋯Cg1^iv	0.93	2.86	3.460 (2)	123
C3B—H3B⋯Cg2^v	0.93	2.60	3.433 (2)	149

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) .

Acknowledgments

The authors acknowledge the Zonguldak Karaelmas University Research Fund (project No. 2012-10-03-12).

supplementary crystallographic information

Comment

Azole compounds have important biological activities. Some indazole derivatives have been known as antifungal (Lebouvier et al., 2007; Park et al., 2007) and antiproliferative agents (Raffa et al., 2009; Plescia et al., 2010; Maggio et al., 2011) and crystal structures have been reported (Gerpe et al., 2007; Raffa et al., 2009). Crystal structures of ketones similar to the titled compound having benzimidazole ring (Özel Güven et al., 2008a) and 1,2,4-triazole ring (Özel Güven et al., 2008b) have been reported. Now we report the crystal structure of the title indazole derivative, (I).

The asymmetric unit of (I) contains two crystallographically independent molecules (Fig. 1), in which the bond lengths and angles are generally within normal ranges. The indazole [B (N1A/N2A/C9A-C15A) and B' (N1B/N2B/C9B-C15B)] ring systems are approximately planar with maximum deviations of -0.013 (2)Å (for atom C13A) and -0.025 (2)Å (for atom C12B), respectively. Their mean planes are oriented with respect to the phenyl [A (C2A-C7A) and A' (C2B-C7B)] rings at dihedral angles of A/B = 50.82 (5) and A'/B' = 89.29 (6) °. The dihedral angles between the rings A, A' and B, B' are A/A' = 78.52 (7) and B/B' = 62.38 (5) °. Atoms C8A and C8B are -0.048 (2) and -0.088 (2) Å away from the corresponding indazole ring planes, while atoms C1A, O1A and C1B, O1B are -0.022 (2), 0.516 (2) Å and -0.024 (2), 0.039 (1) Å away from the corresponding phenyl ring planes.

In the crystal structure, weak intermolecular C—H···O and C—H···N hydrogen bonds, and C—H···π interactions (Table 1) consolidate the packing.

Experimental

The title compound, (I), was synthesized by the reaction of 2-bromo-1-phenylethanone with 1H-imidazole. A mixture of 2-bromo-1-phenylethanone (0.842 g, 4.232 mmol) and 1H-imidazole (1 g, 8.465 mmol) was refluxed in toluene (40 ml) for 9 h. After evaporation of the solvent, the formed precipitate was purified by column chromatography using hexane-ethylacetate (5:1) mixture, and then crystallized from chloroform to obtain colorless crystals suitable for X-ray analysis (yield; 0.22 g, 22%).