2-(2H-Indazol-2-yl)-1-phenyl­ethanone

Özel Güven, Ö.; Türk, G.; Adler, P.D.F.; Coles, S.J.; Hökelek, T.

doi:10.1107/S1600536812051811

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o184

doi:10.1107/S1600536812051811

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

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

^aDepartment of Chemistry, Bülent Ecevit University, 67100 Zonguldak, Turkey, ^bDepartment of Chemistry, Southampton University, SO17 1BJ Southampton, England, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 3 December 2012; accepted 24 December 2012; online 4 January 2013)

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).

Experimental

Crystal data

C₁₅H₁₂N₂O
M_r = 236.27
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.057
wR(F²) = 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

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⋯O1Bⁱ	0.93	2.53	3.418 (2)	159
C8A—H81⋯N2Aⁱⁱ	0.97	2.57	3.519 (3)	164
C8A—H82⋯O1Bⁱⁱⁱ	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
Symmetry codes: (i) x, y, z+1; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x-{\script{1\over 2}}, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812051811/cv5372sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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).

Experimental top

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%).

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2011); cell refinement: CrystalClear-SM Expert (Rigaku, 2011); data reduction: CrystalClear-SM Expert (Rigaku, 2011); 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).

Figures top

Fig. 1. Two independent molecules in (I) with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

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

Crystal data top

C₁₅H₁₂N₂O	F(000) = 992
M_r = 236.27	D_x = 1.345 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15539 reflections
a = 9.4408 (3) Å	θ = 3.1–27.5°
b = 17.9636 (5) Å	µ = 0.09 mm⁻¹
c = 13.9415 (4) Å	T = 100 K
β = 99.247 (4)°	Prism, colorless
V = 2333.62 (12) Å³	0.20 × 0.20 × 0.20 mm
Z = 8

Data collection top

Rigaku Saturn724+ diffractometer	R_int = 0.084
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 3.1°
Graphite monochromator	h = −12→12
profile data from ω–scans	k = −21→23
23377 measured reflections	l = −18→18
5349 independent reflections	3 standard reflections every 2 min
3346 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0558P)²] where P = (F_o² + 2F_c²)/3
5349 reflections	(Δ/σ)_max < 0.001
325 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₂N₂O	V = 2333.62 (12) Å³
M_r = 236.27	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.4408 (3) Å	µ = 0.09 mm⁻¹
b = 17.9636 (5) Å	T = 100 K
c = 13.9415 (4) Å	0.20 × 0.20 × 0.20 mm
β = 99.247 (4)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
5349 reflections	Δρ_min = −0.24 e Å⁻³
325 parameters

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. 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.

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

	x	y	z	U_iso*/U_eq
O1A	0.14439 (19)	0.58400 (8)	0.50109 (10)	0.0407 (5)
N1A	0.26416 (18)	0.46418 (9)	0.42124 (11)	0.0201 (4)
N2A	0.36687 (18)	0.49886 (9)	0.37948 (11)	0.0215 (4)
C1A	0.2002 (2)	0.53784 (11)	0.55820 (14)	0.0229 (5)
C2A	0.2122 (2)	0.54710 (10)	0.66507 (13)	0.0184 (4)
C3A	0.2094 (2)	0.48688 (11)	0.72716 (14)	0.0229 (5)
H3A	0.1993	0.4389	0.7020	0.028*
C4A	0.2214 (2)	0.49816 (11)	0.82645 (14)	0.0255 (5)
H4A	0.2173	0.4579	0.8678	0.031*
C5A	0.2394 (2)	0.56951 (11)	0.86395 (14)	0.0240 (5)
H5A	0.2482	0.5770	0.9306	0.029*
C6A	0.2443 (2)	0.62952 (11)	0.80282 (14)	0.0239 (5)
H6A	0.2583	0.6773	0.8283	0.029*
C7A	0.2285 (2)	0.61847 (11)	0.70379 (14)	0.0225 (5)
H7A	0.2286	0.6591	0.6625	0.027*
C8A	0.2702 (2)	0.46866 (11)	0.52526 (13)	0.0236 (5)
H81	0.3699	0.4676	0.5561	0.028*
H82	0.2234	0.4252	0.5470	0.028*
C9A	0.1661 (2)	0.42712 (11)	0.35829 (13)	0.0221 (5)
H9A	0.0880	0.4003	0.3729	0.026*
C10A	0.2049 (2)	0.43697 (10)	0.26711 (13)	0.0196 (4)
C11A	0.1489 (2)	0.41293 (11)	0.17170 (14)	0.0236 (5)
H11A	0.0663	0.3840	0.1595	0.028*
C12A	0.2199 (2)	0.43368 (11)	0.09856 (14)	0.0255 (5)
H12A	0.1849	0.4187	0.0354	0.031*
C13A	0.3461 (2)	0.47761 (11)	0.11623 (14)	0.0263 (5)
H13A	0.3922	0.4900	0.0643	0.032*
C14A	0.4020 (2)	0.50222 (11)	0.20685 (14)	0.0246 (5)
H14A	0.4844	0.5314	0.2175	0.030*
C15A	0.3296 (2)	0.48162 (10)	0.28413 (13)	0.0191 (4)
O1B	0.19943 (15)	0.80396 (7)	−0.10890 (9)	0.0229 (3)
N1B	−0.01229 (18)	0.77510 (9)	−0.00267 (11)	0.0195 (4)
N2B	0.00706 (18)	0.70086 (9)	0.01224 (11)	0.0202 (4)
C1B	0.0784 (2)	0.80142 (10)	−0.15520 (13)	0.0187 (4)
C2B	0.0524 (2)	0.80064 (10)	−0.26292 (13)	0.0177 (4)
C3B	−0.0848 (2)	0.79327 (12)	−0.31651 (14)	0.0251 (5)
H3B	−0.1635	0.7880	−0.2846	0.030*
C4B	−0.1043 (2)	0.79378 (13)	−0.41696 (14)	0.0312 (5)
H4B	−0.1960	0.7887	−0.4525	0.037*
C5B	0.0122 (2)	0.80181 (12)	−0.46459 (14)	0.0267 (5)
H5B	−0.0016	0.8031	−0.5321	0.032*
C6B	0.1488 (2)	0.80796 (11)	−0.41253 (13)	0.0220 (5)
H6B	0.2271	0.8123	−0.4450	0.026*
C7B	0.1694 (2)	0.80764 (10)	−0.31214 (13)	0.0193 (4)
H7B	0.2616	0.8121	−0.2772	0.023*
C8B	−0.0503 (2)	0.80013 (12)	−0.10227 (13)	0.0220 (5)
H83	−0.0910	0.8497	−0.1028	0.026*
H84	−0.1230	0.7673	−0.1364	0.026*
C9B	0.0048 (2)	0.81611 (11)	0.07851 (13)	0.0200 (5)
H9B	−0.0025	0.8676	0.0826	0.024*
C10B	0.0357 (2)	0.76636 (11)	0.15582 (13)	0.0173 (4)
C11B	0.0610 (2)	0.77194 (11)	0.25834 (13)	0.0209 (5)
H11B	0.0627	0.8179	0.2891	0.025*
C12B	0.0828 (2)	0.70741 (11)	0.31061 (13)	0.0215 (5)
H12B	0.0969	0.7098	0.3781	0.026*
C13B	0.0847 (2)	0.63700 (11)	0.26516 (14)	0.0218 (5)
H13B	0.1013	0.5946	0.3035	0.026*
C14B	0.0627 (2)	0.62993 (11)	0.16617 (14)	0.0214 (5)
H14B	0.0651	0.5836	0.1367	0.026*
C15B	0.0363 (2)	0.69534 (11)	0.11057 (13)	0.0179 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1A	0.0671 (13)	0.0324 (9)	0.0216 (8)	0.0229 (9)	0.0043 (8)	0.0037 (7)
N1A	0.0220 (10)	0.0202 (9)	0.0183 (8)	0.0025 (8)	0.0036 (7)	−0.0013 (7)
N2A	0.0221 (10)	0.0222 (9)	0.0195 (9)	−0.0008 (8)	0.0015 (7)	−0.0010 (7)
C1A	0.0273 (12)	0.0217 (11)	0.0200 (10)	0.0018 (9)	0.0043 (9)	0.0035 (9)
C2A	0.0168 (11)	0.0197 (11)	0.0188 (10)	0.0016 (8)	0.0034 (8)	0.0002 (8)
C3A	0.0257 (12)	0.0185 (11)	0.0250 (11)	−0.0011 (9)	0.0052 (9)	−0.0012 (9)
C4A	0.0324 (13)	0.0230 (11)	0.0221 (10)	0.0034 (10)	0.0071 (9)	0.0051 (9)
C5A	0.0244 (12)	0.0292 (12)	0.0189 (10)	0.0055 (10)	0.0050 (9)	0.0000 (9)
C6A	0.0233 (12)	0.0211 (11)	0.0276 (11)	0.0016 (9)	0.0051 (9)	−0.0043 (9)
C7A	0.0260 (12)	0.0182 (11)	0.0241 (11)	0.0026 (9)	0.0069 (9)	0.0032 (8)
C8A	0.0270 (12)	0.0250 (11)	0.0177 (10)	0.0042 (10)	0.0001 (9)	0.0014 (9)
C9A	0.0202 (11)	0.0205 (11)	0.0257 (11)	−0.0006 (9)	0.0046 (9)	−0.0025 (9)
C10A	0.0192 (11)	0.0169 (10)	0.0223 (10)	0.0031 (9)	0.0021 (8)	−0.0028 (8)
C11A	0.0218 (12)	0.0208 (11)	0.0265 (11)	0.0000 (9)	−0.0009 (9)	−0.0041 (9)
C12A	0.0306 (13)	0.0267 (12)	0.0176 (10)	0.0044 (10)	−0.0012 (9)	−0.0048 (9)
C13A	0.0301 (13)	0.0281 (12)	0.0218 (11)	0.0043 (10)	0.0072 (9)	0.0019 (9)
C14A	0.0230 (12)	0.0230 (11)	0.0268 (11)	−0.0020 (9)	0.0009 (9)	0.0017 (9)
C15A	0.0213 (11)	0.0176 (10)	0.0174 (10)	0.0037 (8)	0.0002 (8)	−0.0010 (8)
O1B	0.0217 (8)	0.0265 (8)	0.0193 (7)	−0.0010 (6)	0.0002 (6)	−0.0010 (6)
N1B	0.0206 (10)	0.0218 (9)	0.0162 (8)	0.0006 (7)	0.0030 (7)	−0.0001 (7)
N2B	0.0209 (10)	0.0200 (9)	0.0189 (8)	0.0002 (7)	0.0003 (7)	−0.0013 (7)
C1B	0.0231 (12)	0.0121 (10)	0.0198 (10)	0.0015 (9)	−0.0002 (9)	−0.0011 (8)
C2B	0.0197 (11)	0.0151 (10)	0.0187 (9)	0.0038 (8)	0.0041 (8)	0.0001 (8)
C3B	0.0205 (12)	0.0347 (13)	0.0211 (10)	0.0012 (10)	0.0063 (9)	−0.0017 (9)
C4B	0.0217 (13)	0.0483 (15)	0.0224 (11)	0.0012 (11)	−0.0005 (9)	−0.0044 (10)
C5B	0.0301 (13)	0.0343 (13)	0.0156 (10)	0.0081 (10)	0.0032 (9)	0.0019 (9)
C6B	0.0269 (13)	0.0205 (11)	0.0210 (10)	0.0015 (9)	0.0108 (9)	0.0035 (8)
C7B	0.0174 (11)	0.0150 (10)	0.0243 (10)	0.0007 (8)	−0.0006 (9)	0.0002 (8)
C8B	0.0181 (11)	0.0291 (12)	0.0173 (10)	0.0027 (9)	−0.0010 (8)	0.0005 (9)
C9B	0.0219 (12)	0.0194 (11)	0.0191 (10)	−0.0005 (9)	0.0048 (9)	−0.0021 (8)
C10B	0.0130 (10)	0.0217 (11)	0.0170 (10)	−0.0015 (8)	0.0023 (8)	0.0005 (8)
C11B	0.0187 (11)	0.0249 (11)	0.0197 (10)	−0.0001 (9)	0.0046 (9)	−0.0030 (9)
C12B	0.0166 (11)	0.0319 (12)	0.0158 (9)	−0.0009 (9)	0.0022 (8)	−0.0009 (9)
C13B	0.0215 (11)	0.0219 (11)	0.0216 (10)	0.0013 (9)	0.0016 (9)	0.0032 (8)
C14B	0.0215 (12)	0.0187 (11)	0.0243 (11)	−0.0001 (9)	0.0047 (9)	−0.0022 (9)
C15B	0.0133 (10)	0.0243 (11)	0.0160 (9)	−0.0019 (9)	0.0023 (8)	0.0000 (8)

Geometric parameters (Å, º) top

O1A—C1A	1.210 (2)	O1B—C1B	1.219 (2)
N1A—C8A	1.444 (2)	N1B—C8B	1.449 (2)
N1A—C9A	1.345 (2)	N1B—C9B	1.338 (2)
N2A—N1A	1.360 (2)	N2B—N1B	1.357 (2)
N2A—C15A	1.355 (2)	N2B—C15B	1.358 (2)
C1A—C2A	1.485 (3)	C1B—C8B	1.520 (3)
C1A—C8A	1.513 (3)	C2B—C1B	1.482 (3)
C2A—C3A	1.388 (3)	C2B—C3B	1.394 (3)
C2A—C7A	1.390 (3)	C2B—C7B	1.396 (3)
C3A—C4A	1.385 (3)	C3B—C4B	1.383 (3)
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C4A	1.384 (3)	C5B—C4B	1.380 (3)
C5A—C6A	1.380 (3)	C5B—H5B	0.9300
C5A—H5A	0.9300	C6B—C5B	1.379 (3)
C6A—H6A	0.9300	C6B—C7B	1.382 (2)
C7A—C6A	1.379 (3)	C6B—H6B	0.9300
C7A—H7A	0.9300	C7B—H7B	0.9300
C8A—H81	0.9700	C8B—H83	0.9700
C8A—H82	0.9700	C8B—H84	0.9700
C9A—C10A	1.389 (3)	C9B—C10B	1.395 (3)
C9A—H9A	0.9300	C9B—H9B	0.9300
C10A—C11A	1.417 (3)	C10B—C11B	1.414 (2)
C11A—H11A	0.9300	C11B—C12B	1.367 (3)
C12A—C11A	1.360 (3)	C11B—H11B	0.9300
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C12A	1.417 (3)	C13B—C12B	1.416 (3)
C13A—C14A	1.362 (3)	C13B—C14B	1.368 (3)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—C10A	1.413 (3)	C15B—C10B	1.424 (3)
C15A—C14A	1.415 (3)	C15B—C14B	1.408 (3)

N2A—N1A—C8A	119.24 (16)	N2B—N1B—C8B	117.27 (15)
C9A—N1A—N2A	114.25 (15)	C9B—N1B—N2B	114.60 (15)
C9A—N1A—C8A	126.50 (17)	C9B—N1B—C8B	128.12 (17)
C15A—N2A—N1A	102.99 (15)	N1B—N2B—C15B	103.12 (15)
O1A—C1A—C2A	122.58 (18)	O1B—C1B—C2B	121.69 (18)
O1A—C1A—C8A	121.89 (17)	O1B—C1B—C8B	119.85 (16)
C2A—C1A—C8A	115.43 (16)	C2B—C1B—C8B	118.45 (17)
C3A—C2A—C1A	122.15 (17)	C3B—C2B—C1B	122.16 (18)
C3A—C2A—C7A	119.24 (17)	C3B—C2B—C7B	119.05 (17)
C7A—C2A—C1A	118.61 (17)	C7B—C2B—C1B	118.79 (18)
C2A—C3A—H3A	119.9	C2B—C3B—H3B	119.9
C4A—C3A—C2A	120.15 (19)	C4B—C3B—C2B	120.2 (2)
C4A—C3A—H3A	119.9	C4B—C3B—H3B	119.9
C3A—C4A—H4A	120.1	C3B—C4B—H4B	119.9
C5A—C4A—C3A	119.87 (19)	C5B—C4B—C3B	120.1 (2)
C5A—C4A—H4A	120.1	C5B—C4B—H4B	119.9
C4A—C5A—H5A	119.9	C4B—C5B—H5B	119.8
C6A—C5A—C4A	120.30 (18)	C6B—C5B—C4B	120.34 (18)
C6A—C5A—H5A	119.9	C6B—C5B—H5B	119.8
C5A—C6A—H6A	120.1	C5B—C6B—C7B	119.99 (19)
C7A—C6A—C5A	119.80 (19)	C5B—C6B—H6B	120.0
C7A—C6A—H6A	120.1	C7B—C6B—H6B	120.0
C2A—C7A—H7A	119.7	C2B—C7B—H7B	119.8
C6A—C7A—C2A	120.60 (18)	C6B—C7B—C2B	120.31 (19)
C6A—C7A—H7A	119.7	C6B—C7B—H7B	119.8
N1A—C8A—C1A	113.68 (16)	N1B—C8B—C1B	112.07 (16)
N1A—C8A—H81	108.8	N1B—C8B—H83	109.2
N1A—C8A—H82	108.8	N1B—C8B—H84	109.2
C1A—C8A—H81	108.8	C1B—C8B—H83	109.2
C1A—C8A—H82	108.8	C1B—C8B—H84	109.2
H81—C8A—H82	107.7	H83—C8B—H84	107.9
N1A—C9A—C10A	106.21 (18)	N1B—C9B—C10B	106.42 (17)
N1A—C9A—H9A	126.9	N1B—C9B—H9B	126.8
C10A—C9A—H9A	126.9	C10B—C9B—H9B	126.8
C9A—C10A—C11A	134.95 (19)	C9B—C10B—C11B	135.73 (18)
C9A—C10A—C15A	104.68 (17)	C9B—C10B—C15B	104.30 (16)
C15A—C10A—C11A	120.37 (18)	C11B—C10B—C15B	119.96 (17)
C12A—C11A—C10A	117.76 (19)	C10B—C11B—H11B	121.1
C12A—C11A—H11A	121.1	C12B—C11B—C10B	117.71 (18)
C10A—C11A—H11A	121.1	C12B—C11B—H11B	121.1
C11A—C12A—C13A	121.64 (18)	C11B—C12B—C13B	122.04 (17)
C11A—C12A—H12A	119.2	C11B—C12B—H12B	119.0
C13A—C12A—H12A	119.2	C13B—C12B—H12B	119.0
C12A—C13A—H13A	118.9	C12B—C13B—H13B	119.2
C14A—C13A—C12A	122.1 (2)	C14B—C13B—C12B	121.56 (18)
C14A—C13A—H13A	118.9	C14B—C13B—H13B	119.2
C13A—C14A—C15A	117.3 (2)	C13B—C14B—C15B	117.57 (18)
C13A—C14A—H14A	121.3	C13B—C14B—H14B	121.2
C15A—C14A—H14A	121.3	C15B—C14B—H14B	121.2
N2A—C15A—C10A	111.87 (17)	N2B—C15B—C10B	111.55 (17)
N2A—C15A—C14A	127.32 (19)	N2B—C15B—C14B	127.32 (18)
C10A—C15A—C14A	120.80 (17)	C14B—C15B—C10B	121.12 (16)

N2A—N1A—C8A—C1A	85.3 (2)	N2B—N1B—C8B—C1B	−77.3 (2)
C9A—N1A—C8A—C1A	−96.0 (2)	C9B—N1B—C8B—C1B	103.7 (2)
N2A—N1A—C9A—C10A	0.2 (2)	N2B—N1B—C9B—C10B	−1.2 (2)
C8A—N1A—C9A—C10A	−178.57 (17)	C8B—N1B—C9B—C10B	177.81 (18)
C15A—N2A—N1A—C8A	178.61 (16)	C15B—N2B—N1B—C8B	−178.14 (16)
C15A—N2A—N1A—C9A	−0.3 (2)	C15B—N2B—N1B—C9B	1.0 (2)
N1A—N2A—C15A—C10A	0.2 (2)	N1B—N2B—C15B—C10B	−0.4 (2)
N1A—N2A—C15A—C14A	−178.65 (19)	N1B—N2B—C15B—C14B	178.66 (19)
O1A—C1A—C2A—C3A	148.4 (2)	O1B—C1B—C8B—N1B	−21.2 (3)
O1A—C1A—C2A—C7A	−32.3 (3)	C2B—C1B—C8B—N1B	159.71 (16)
C8A—C1A—C2A—C3A	−35.1 (3)	C3B—C2B—C1B—O1B	176.09 (18)
C8A—C1A—C2A—C7A	144.24 (19)	C3B—C2B—C1B—C8B	−4.8 (3)
O1A—C1A—C8A—N1A	0.4 (3)	C7B—C2B—C1B—O1B	−4.0 (3)
C2A—C1A—C8A—N1A	−176.21 (17)	C7B—C2B—C1B—C8B	175.09 (17)
C1A—C2A—C3A—C4A	179.82 (19)	C1B—C2B—C3B—C4B	179.16 (19)
C7A—C2A—C3A—C4A	0.5 (3)	C7B—C2B—C3B—C4B	−0.7 (3)
C1A—C2A—C7A—C6A	−178.09 (19)	C1B—C2B—C7B—C6B	−179.28 (17)
C3A—C2A—C7A—C6A	1.2 (3)	C3B—C2B—C7B—C6B	0.6 (3)
C2A—C3A—C4A—C5A	−1.4 (3)	C2B—C3B—C4B—C5B	−0.2 (3)
C6A—C5A—C4A—C3A	0.5 (3)	C6B—C5B—C4B—C3B	1.2 (3)
C4A—C5A—C6A—C7A	1.2 (3)	C7B—C6B—C5B—C4B	−1.3 (3)
C2A—C7A—C6A—C5A	−2.1 (3)	C5B—C6B—C7B—C2B	0.4 (3)
N1A—C9A—C10A—C11A	179.7 (2)	N1B—C9B—C10B—C11B	−177.8 (2)
N1A—C9A—C10A—C15A	−0.1 (2)	N1B—C9B—C10B—C15B	0.8 (2)
C9A—C10A—C11A—C12A	−179.0 (2)	C9B—C10B—C11B—C12B	177.4 (2)
C15A—C10A—C11A—C12A	0.6 (3)	C15B—C10B—C11B—C12B	−1.1 (3)
C13A—C12A—C11A—C10A	0.2 (3)	C10B—C11B—C12B—C13B	1.8 (3)
C14A—C13A—C12A—C11A	−0.9 (3)	C14B—C13B—C12B—C11B	−0.9 (3)
C12A—C13A—C14A—C15A	0.6 (3)	C12B—C13B—C14B—C15B	−0.7 (3)
N2A—C15A—C10A—C9A	−0.1 (2)	N2B—C15B—C10B—C9B	−0.3 (2)
N2A—C15A—C10A—C11A	−179.87 (17)	N2B—C15B—C10B—C11B	178.66 (17)
C14A—C15A—C10A—C9A	178.84 (18)	C14B—C15B—C10B—C9B	−179.40 (18)
C14A—C15A—C10A—C11A	−0.9 (3)	C14B—C15B—C10B—C11B	−0.5 (3)
N2A—C15A—C14A—C13A	179.07 (19)	N2B—C15B—C14B—C13B	−177.60 (19)
C10A—C15A—C14A—C13A	0.3 (3)	C10B—C15B—C14B—C13B	1.4 (3)

Hydrogen-bond geometry (Å, º) top

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···O1Bⁱ	0.93	2.53	3.418 (2)	159
C8A—H81···N2Aⁱⁱ	0.97	2.57	3.519 (3)	164
C8A—H82···O1Bⁱⁱⁱ	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

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O
M_r	236.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.4408 (3), 17.9636 (5), 13.9415 (4)
β (°)	99.247 (4)
V (Å³)	2333.62 (12)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Saturn724+ diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23377, 5349, 3346
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.129, 1.02
No. of reflections	5349
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.24

Computer programs: CrystalClear-SM Expert (Rigaku, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX publication routines (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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···O1Bⁱ	0.93	2.53	3.418 (2)	159
C8A—H81···N2Aⁱⁱ	0.97	2.57	3.519 (3)	164
C8A—H82···O1Bⁱⁱⁱ	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

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

Acknowledgements

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

References

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Volume 69| Part 2| February 2013| Page o184

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