2-(2H-Indazol-2-yl)-1-phenyl-ethanone.

The asymmetric unit of the title compound, C(15)H(12)N(2)O, contains two independent mol-ecules with different conformations, the phenyl ring and indazole mean plane in the two mol-ecules 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 inter-actions 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 = 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

Δρmax = 0.30 e Å−3

Δρmin = −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 ▶).

Click here for additional data file.

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

Click here for additional data file.

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

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

C15H12N2O	F(000) = 992
Mr = 236.27	Dx = 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

Rigaku Saturn724+ diffractometer	Rint = 0.084
Radiation source: fine-focus sealed tube	θmax = 27.5°, θmin = 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 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(Fo2) + (0.0558P)2] where P = (Fo2 + 2Fc2)/3
5349 reflections	(Δ/σ)max < 0.001
325 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···Cg1iv	0.93	2.86	3.460 (2)	123
C3B—H3B···Cg2v	0.93	2.60	3.433 (2)	149

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⋯Cg1iv	0.93	2.86	3.460 (2)	123
C3B—H3B⋯Cg2v	0.93	2.60	3.433 (2)	149

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