2-{(E)-N-[2-(1H-Inden-3-yl)eth-yl]imino-meth-yl}-1H-imidazole.

The asymmetric unit of the title compound, C(15)H(15)N(3), contains two crystallographically independent mol-ecules with very similar geometries. The imidazole and indenyl planes are approximately orthogonal, making dihedral angles of 88.21 (9) and 83.08 (9)%deg; in the two independent molecules. In the crystal, the imidazole units are linked by N-H⋯N hydrogen bonds into chains parallel to the 101) plane stretched in the diagonal direction [translation vector ([Formula: see text],1,0); C(4) motif]. Within a chain, there are two types of symmetrically non-equivalent alternating H-bonds which slightly differ in their parameters.

Related literature

For the structural parameters of 3-organyl substituted 1H-indenes (organic structures only), see: Sun et al. (2010 ▶) and references cited therein. For the structural parameters of 2-organyl-1H-imidazoles (organic structures only, not bi- or oligocyclic, non-ionic, recent publications only), see: Lassalle-Kaiser et al. (2006 ▶). For the structural parameters of Li, Ti, and Zr complexes derived from 1H-imidazol(in)-2-yl side-chain-functionalized cyclo­penta­dienes see: Krut’ko et al. (2006 ▶); Nie et al. (2008 ▶); Wang et al. (2009 ▶); Ge et al. (2010 ▶). For the structural parameters of 1H-imidazol(in)-2-yl side-chain-functionalized 3-substituted 1H-indene and Li-indenide, see: Sun et al. (2009 ▶, 2010 ▶). For graph-set notation, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For preparation of 2-(1H-inden-3-yl)ethanamine, see: Winter et al. (1967 ▶).

Experimental

Crystal data

C15H15N3

M = 237.30

Orthorhombic,

a = 5.8827 (5) Å

b = 8.3326 (7) Å

c = 51.909 (4) Å

V = 2544.5 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.36 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.973, T max = 0.990

13315 measured reflections

2939 independent reflections

2328 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.113

S = 1.03

2939 reflections

333 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXTL and OLEX2.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811013286/im2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013286/im2276Isup2.hkl

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

C15H15N3	F(000) = 1008
Mr = 237.30	Dx = 1.239 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8457 reflections
a = 5.8827 (5) Å	θ = 2.4–28.2°
b = 8.3326 (7) Å	µ = 0.08 mm−1
c = 51.909 (4) Å	T = 296 K
V = 2544.5 (4) Å3	Block, colourless
Z = 8	0.36 × 0.22 × 0.14 mm

Bruker SMART APEXII diffractometer	2939 independent reflections
Radiation source: fine-focus sealed tube	2328 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 8.333 pixels mm-1	θmax = 26.0°, θmin = 2.4°
φ and ω scans	h = −7→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −10→10
Tmin = 0.973, Tmax = 0.990	l = −64→61
13315 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.057P)2 + 0.4576P] where P = (Fo2 + 2Fc2)/3
2939 reflections	(Δ/σ)max = 0.001
333 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Experimental. — NMR spectra were recorded on a Varian INOVA-400 instrument in CDCl3 at 298 K. For 1H and 13C{1H} spectra, the TMS resonances (δH = 0.0 and δC = 0.0) were used as internal reference standards. — Chromato-mass spectrum was measured on Agilent 6890 Series GC system equipped with HP 5973 mass-selective detector. — 1H NMR: δ = 2.93 (m, 2 H, Indenyl—CH2), 3.34 (m, 2 H, CH2 in indene), 3.95 (m, 2 H, NCH2), 6.27 (m, 1 H, C═CH in indene), 7.15 (br s, 2 H, HC═CH in imidazole), 7.21, 7.30, 7.38, 7.46 (all m, all 1 H, CH in benzene ring of indene), 8.22 (m, 1 H, HC═N). — 13C{1H} NMR: δ = 29.02 (Indenyl—CH2), 37.78 (NCH2), 59.13 (CH2 in indene), 118.70 (═ CH in indene), 118.23, 130.60 (both br, HC═CH in imidazole), 123.79, 124.68, 125.98, 129.24 (CH in benzene ring of indene), 141.38 (═C in indene), 144.24, 144.88 (C in benzene ring of indene), 152.86 (HC═N). — EI MS (70 eV) m/z (%): 237 (8) [M], 141 (9) [benztropilium], 128 (28) [benzpentafulvene], 115 (13) [indenilium], 109 (100) [C5H7N3], 108 (36) [C5H6N3], 82 (25) [C4H6N2], 81 (82) [C4H5N2].

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.

	x	y	z	Uiso*/Ueq
N1A	0.6784 (5)	0.2550 (3)	0.62194 (4)	0.0481 (6)
H1A	0.616 (7)	0.334 (5)	0.6273 (7)	0.092 (15)*
N2A	0.9145 (4)	0.0506 (3)	0.61856 (4)	0.0490 (6)
N3A	0.9748 (5)	0.3849 (3)	0.66146 (4)	0.0510 (6)
C1A	0.8760 (5)	0.1896 (3)	0.63011 (5)	0.0439 (7)
C2A	0.5871 (6)	0.1520 (4)	0.60450 (5)	0.0549 (8)
H2A	0.4512	0.1645	0.5956	0.066*
C3A	0.7330 (5)	0.0284 (4)	0.60277 (5)	0.0534 (8)
H3A	0.7125	−0.0604	0.5922	0.064*
C4A	1.0258 (5)	0.2616 (4)	0.64897 (5)	0.0478 (7)
H4A	1.1664	0.2141	0.6519	0.057*
C5A	1.1416 (6)	0.4457 (4)	0.67957 (5)	0.0556 (8)
H5AA	1.1685	0.5587	0.6762	0.067*
H5AB	1.2841	0.3889	0.6772	0.067*
C6A	1.0601 (5)	0.4243 (4)	0.70698 (5)	0.0510 (8)
H6AA	0.9112	0.4731	0.7086	0.061*
H6AB	1.0437	0.3105	0.7104	0.061*
C7A	1.2152 (5)	0.4959 (3)	0.72690 (5)	0.0407 (6)
C8A	1.4034 (5)	0.5814 (4)	0.72351 (5)	0.0518 (7)
H8A	1.4662	0.6050	0.7075	0.062*
C9A	1.5019 (6)	0.6351 (4)	0.74873 (7)	0.0600 (8)
H9AA	1.6560	0.5959	0.7509	0.072*
H9AB	1.5016	0.7512	0.7501	0.072*
C10A	1.3448 (5)	0.5610 (3)	0.76792 (5)	0.0463 (7)
C11A	1.1729 (5)	0.4801 (3)	0.75462 (5)	0.0393 (6)
C12A	1.0062 (5)	0.3973 (3)	0.76790 (5)	0.0500 (7)
H12A	0.8936	0.3419	0.7590	0.060*
C13A	1.0092 (7)	0.3980 (4)	0.79442 (5)	0.0621 (9)
H13A	0.8967	0.3441	0.8036	0.074*
C14A	1.1783 (7)	0.4783 (5)	0.80745 (6)	0.0680 (10)
H14A	1.1796	0.4766	0.8254	0.082*
C15A	1.3455 (7)	0.5612 (4)	0.79457 (6)	0.0654 (10)
H15A	1.4572	0.6164	0.8036	0.078*
N1B	0.2511 (4)	0.7865 (3)	0.62860 (4)	0.0468 (6)
H1B	0.143 (6)	0.860 (4)	0.6239 (6)	0.071 (11)*
N2B	0.4626 (4)	0.5689 (3)	0.62951 (4)	0.0510 (6)
N3B	−0.0309 (5)	0.6341 (3)	0.59023 (4)	0.0513 (6)
C1B	0.2802 (5)	0.6370 (4)	0.61924 (5)	0.0443 (7)
C2B	0.4232 (5)	0.8149 (4)	0.64549 (5)	0.0541 (8)
H2B	0.4474	0.9081	0.6549	0.065*
C3B	0.5514 (5)	0.6812 (4)	0.64584 (5)	0.0527 (8)
H3B	0.6816	0.6673	0.6557	0.063*
C4B	0.1292 (5)	0.5614 (4)	0.60103 (5)	0.0473 (7)
H4B	0.1518	0.4536	0.5971	0.057*
C5B	−0.1762 (6)	0.5435 (4)	0.57281 (5)	0.0577 (8)
H5BA	−0.3337	0.5575	0.5778	0.069*
H5BB	−0.1399	0.4302	0.5741	0.069*
C6B	−0.1461 (5)	0.5976 (4)	0.54526 (5)	0.0497 (7)
H6BA	−0.1654	0.7131	0.5444	0.060*
H6BB	0.0077	0.5731	0.5398	0.060*
C7B	−0.3092 (5)	0.5204 (3)	0.52707 (5)	0.0414 (6)
C8B	−0.4903 (5)	0.4293 (4)	0.53233 (5)	0.0529 (7)
H8B	−0.5359	0.4018	0.5489	0.063*
C9B	−0.6111 (5)	0.3769 (4)	0.50844 (6)	0.0560 (8)
H9BA	−0.6134	0.2609	0.5070	0.067*
H9BB	−0.7658	0.4170	0.5081	0.067*
C10B	−0.4709 (5)	0.4507 (3)	0.48763 (5)	0.0459 (7)
C11B	−0.2911 (4)	0.5363 (3)	0.49889 (5)	0.0388 (6)
C12B	−0.1338 (5)	0.6134 (4)	0.48353 (5)	0.0507 (7)
H12B	−0.0144	0.6706	0.4908	0.061*
C13B	−0.1569 (6)	0.6040 (4)	0.45713 (6)	0.0631 (9)
H13B	−0.0517	0.6558	0.4467	0.076*
C14B	−0.3317 (6)	0.5201 (4)	0.44599 (6)	0.0642 (9)
H14B	−0.3437	0.5154	0.4281	0.077*
C15B	−0.4900 (6)	0.4426 (4)	0.46121 (6)	0.0578 (8)
H15B	−0.6085	0.3854	0.4537	0.069*

	U11	U22	U33	U12	U13	U23
N1A	0.0537 (16)	0.0473 (15)	0.0431 (12)	0.0049 (13)	−0.0006 (12)	−0.0032 (11)
N2A	0.0555 (15)	0.0510 (14)	0.0405 (11)	0.0040 (13)	−0.0006 (11)	−0.0071 (11)
N3A	0.0610 (16)	0.0558 (15)	0.0361 (10)	0.0018 (14)	−0.0071 (12)	−0.0014 (11)
C1A	0.0502 (16)	0.0463 (16)	0.0352 (12)	0.0020 (14)	0.0010 (13)	0.0042 (12)
C2A	0.0556 (18)	0.060 (2)	0.0493 (15)	−0.0018 (17)	−0.0098 (15)	−0.0027 (14)
C3A	0.0610 (18)	0.0567 (19)	0.0425 (14)	−0.0020 (17)	−0.0021 (14)	−0.0092 (14)
C4A	0.0515 (17)	0.0516 (17)	0.0404 (13)	0.0030 (15)	−0.0016 (14)	0.0024 (13)
C5A	0.0615 (19)	0.057 (2)	0.0488 (15)	−0.0048 (17)	−0.0009 (15)	−0.0056 (14)
C6A	0.0495 (17)	0.060 (2)	0.0429 (13)	−0.0078 (16)	−0.0047 (13)	−0.0053 (13)
C7A	0.0378 (14)	0.0359 (14)	0.0485 (14)	0.0015 (13)	−0.0039 (12)	−0.0006 (12)
C8A	0.0460 (16)	0.0516 (18)	0.0578 (16)	−0.0050 (15)	−0.0026 (14)	0.0062 (14)
C9A	0.0421 (15)	0.0497 (17)	0.088 (2)	−0.0053 (15)	−0.0163 (16)	−0.0005 (16)
C10A	0.0431 (15)	0.0377 (15)	0.0582 (16)	0.0068 (14)	−0.0153 (14)	−0.0095 (13)
C11A	0.0414 (15)	0.0312 (13)	0.0453 (13)	0.0047 (12)	−0.0065 (12)	−0.0030 (11)
C12A	0.0539 (17)	0.0439 (16)	0.0521 (15)	−0.0039 (15)	−0.0037 (15)	−0.0002 (13)
C13A	0.076 (2)	0.062 (2)	0.0486 (15)	0.007 (2)	0.0017 (17)	0.0053 (15)
C14A	0.088 (3)	0.072 (2)	0.0447 (16)	0.022 (2)	−0.0061 (18)	−0.0082 (16)
C15A	0.073 (2)	0.060 (2)	0.0635 (19)	0.010 (2)	−0.0289 (18)	−0.0162 (17)
N1B	0.0498 (15)	0.0462 (14)	0.0445 (12)	0.0052 (13)	−0.0047 (12)	−0.0026 (11)
N2B	0.0510 (15)	0.0540 (15)	0.0480 (12)	0.0078 (13)	0.0008 (12)	0.0008 (12)
N3B	0.0612 (15)	0.0544 (15)	0.0384 (11)	−0.0022 (14)	−0.0042 (12)	−0.0049 (11)
C1B	0.0484 (16)	0.0462 (16)	0.0382 (12)	0.0013 (14)	0.0033 (13)	0.0007 (12)
C2B	0.0565 (19)	0.0560 (19)	0.0498 (15)	−0.0073 (17)	−0.0081 (15)	−0.0078 (14)
C3B	0.0495 (17)	0.062 (2)	0.0464 (15)	−0.0006 (16)	−0.0071 (14)	0.0015 (14)
C4B	0.0630 (18)	0.0413 (15)	0.0376 (13)	0.0011 (15)	0.0012 (13)	0.0026 (12)
C5B	0.0613 (19)	0.063 (2)	0.0486 (15)	−0.0129 (18)	−0.0072 (15)	−0.0007 (14)
C6B	0.0500 (17)	0.0567 (18)	0.0422 (13)	−0.0045 (15)	−0.0042 (13)	−0.0030 (13)
C7B	0.0404 (14)	0.0396 (15)	0.0442 (13)	−0.0017 (13)	−0.0025 (12)	−0.0034 (12)
C8B	0.0511 (17)	0.0542 (18)	0.0532 (15)	−0.0044 (16)	0.0016 (14)	0.0039 (14)
C9B	0.0413 (16)	0.0535 (18)	0.0732 (19)	−0.0068 (15)	−0.0060 (15)	−0.0093 (15)
C10B	0.0419 (15)	0.0378 (14)	0.0580 (15)	0.0063 (13)	−0.0094 (14)	−0.0076 (13)
C11B	0.0378 (13)	0.0297 (13)	0.0489 (14)	0.0034 (12)	−0.0062 (12)	−0.0042 (11)
C12B	0.0501 (17)	0.0502 (17)	0.0520 (15)	−0.0043 (16)	−0.0040 (14)	−0.0018 (13)
C13B	0.067 (2)	0.071 (2)	0.0509 (16)	0.000 (2)	0.0056 (16)	−0.0003 (16)
C14B	0.072 (2)	0.074 (2)	0.0472 (15)	0.014 (2)	−0.0115 (17)	−0.0101 (16)
C15B	0.0548 (18)	0.0578 (19)	0.0608 (17)	0.0079 (17)	−0.0197 (16)	−0.0173 (15)

N1A—C1A	1.352 (4)	N1B—C1B	1.348 (4)
N1A—C2A	1.358 (4)	N1B—C2B	1.360 (4)
N1A—H1A	0.80 (4)	N1B—H1B	0.92 (4)
N2A—C1A	1.324 (4)	N2B—C1B	1.326 (4)
N2A—C3A	1.359 (4)	N2B—C3B	1.366 (4)
N3A—C4A	1.251 (3)	N3B—C4B	1.253 (4)
N3A—C5A	1.451 (4)	N3B—C5B	1.456 (4)
C1A—C4A	1.448 (4)	C1B—C4B	1.442 (4)
C2A—C3A	1.344 (4)	C2B—C3B	1.345 (4)
C2A—H2A	0.9300	C2B—H2B	0.9300
C3A—H3A	0.9300	C3B—H3B	0.9300
C4A—H4A	0.9300	C4B—H4B	0.9300
C5A—C6A	1.512 (4)	C5B—C6B	1.510 (4)
C5A—H5AA	0.9700	C5B—H5BA	0.9700
C5A—H5AB	0.9700	C5B—H5BB	0.9700
C6A—C7A	1.502 (4)	C6B—C7B	1.492 (4)
C6A—H6AA	0.9700	C6B—H6BA	0.9700
C6A—H6AB	0.9700	C6B—H6BB	0.9700
C7A—C8A	1.328 (4)	C7B—C8B	1.336 (4)
C7A—C11A	1.466 (3)	C7B—C11B	1.473 (3)
C8A—C9A	1.500 (4)	C8B—C9B	1.495 (4)
C8A—H8A	0.9300	C8B—H8B	0.9300
C9A—C10A	1.492 (5)	C9B—C10B	1.491 (4)
C9A—H9AA	0.9700	C9B—H9BA	0.9700
C9A—H9AB	0.9700	C9B—H9BB	0.9700
C10A—C15A	1.383 (4)	C10B—C15B	1.377 (4)
C10A—C11A	1.397 (4)	C10B—C11B	1.403 (4)
C11A—C12A	1.383 (4)	C11B—C12B	1.380 (4)
C12A—C13A	1.377 (4)	C12B—C13B	1.379 (4)
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—C14A	1.377 (5)	C13B—C14B	1.371 (5)
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—C15A	1.375 (5)	C14B—C15B	1.382 (5)
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C1A—N1A—C2A	107.1 (3)	C1B—N1B—C2B	107.4 (3)
C1A—N1A—H1A	128 (3)	C1B—N1B—H1B	128 (2)
C2A—N1A—H1A	124 (3)	C2B—N1B—H1B	125 (2)
C1A—N2A—C3A	104.9 (3)	C1B—N2B—C3B	105.4 (3)
C4A—N3A—C5A	117.4 (3)	C4B—N3B—C5B	118.0 (3)
N2A—C1A—N1A	111.0 (3)	N2B—C1B—N1B	110.6 (3)
N2A—C1A—C4A	124.4 (3)	N2B—C1B—C4B	125.1 (3)
N1A—C1A—C4A	124.7 (3)	N1B—C1B—C4B	124.2 (3)
C3A—C2A—N1A	106.0 (3)	C3B—C2B—N1B	106.4 (3)
C3A—C2A—H2A	127.0	C3B—C2B—H2B	126.8
N1A—C2A—H2A	127.0	N1B—C2B—H2B	126.8
C2A—C3A—N2A	110.9 (3)	C2B—C3B—N2B	110.1 (3)
C2A—C3A—H3A	124.5	C2B—C3B—H3B	124.9
N2A—C3A—H3A	124.5	N2B—C3B—H3B	124.9
N3A—C4A—C1A	123.0 (3)	N3B—C4B—C1B	123.0 (3)
N3A—C4A—H4A	118.5	N3B—C4B—H4B	118.5
C1A—C4A—H4A	118.5	C1B—C4B—H4B	118.5
N3A—C5A—C6A	110.7 (2)	N3B—C5B—C6B	111.4 (3)
N3A—C5A—H5AA	109.5	N3B—C5B—H5BA	109.4
C6A—C5A—H5AA	109.5	C6B—C5B—H5BA	109.4
N3A—C5A—H5AB	109.5	N3B—C5B—H5BB	109.4
C6A—C5A—H5AB	109.5	C6B—C5B—H5BB	109.4
H5AA—C5A—H5AB	108.1	H5BA—C5B—H5BB	108.0
C7A—C6A—C5A	114.1 (2)	C7B—C6B—C5B	113.3 (3)
C7A—C6A—H6AA	108.7	C7B—C6B—H6BA	108.9
C5A—C6A—H6AA	108.7	C5B—C6B—H6BA	108.9
C7A—C6A—H6AB	108.7	C7B—C6B—H6BB	108.9
C5A—C6A—H6AB	108.7	C5B—C6B—H6BB	108.9
H6AA—C6A—H6AB	107.6	H6BA—C6B—H6BB	107.7
C8A—C7A—C11A	108.6 (3)	C8B—C7B—C11B	108.2 (2)
C8A—C7A—C6A	128.9 (3)	C8B—C7B—C6B	128.9 (2)
C11A—C7A—C6A	122.5 (2)	C11B—C7B—C6B	122.9 (2)
C7A—C8A—C9A	111.5 (3)	C7B—C8B—C9B	112.0 (3)
C7A—C8A—H8A	124.3	C7B—C8B—H8B	124.0
C9A—C8A—H8A	124.3	C9B—C8B—H8B	124.0
C10A—C9A—C8A	102.7 (3)	C10B—C9B—C8B	102.6 (2)
C10A—C9A—H9AA	111.2	C10B—C9B—H9BA	111.2
C8A—C9A—H9AA	111.2	C8B—C9B—H9BA	111.2
C10A—C9A—H9AB	111.2	C10B—C9B—H9BB	111.2
C8A—C9A—H9AB	111.2	C8B—C9B—H9BB	111.2
H9AA—C9A—H9AB	109.1	H9BA—C9B—H9BB	109.2
C15A—C10A—C11A	119.8 (3)	C15B—C10B—C11B	120.1 (3)
C15A—C10A—C9A	131.7 (3)	C15B—C10B—C9B	131.0 (3)
C11A—C10A—C9A	108.5 (2)	C11B—C10B—C9B	108.9 (2)
C12A—C11A—C10A	120.5 (2)	C12B—C11B—C10B	120.1 (2)
C12A—C11A—C7A	130.8 (3)	C12B—C11B—C7B	131.6 (3)
C10A—C11A—C7A	108.6 (2)	C10B—C11B—C7B	108.3 (2)
C13A—C12A—C11A	119.2 (3)	C13B—C12B—C11B	118.8 (3)
C13A—C12A—H12A	120.4	C13B—C12B—H12B	120.6
C11A—C12A—H12A	120.4	C11B—C12B—H12B	120.6
C14A—C13A—C12A	120.2 (3)	C14B—C13B—C12B	121.5 (3)
C14A—C13A—H13A	119.9	C14B—C13B—H13B	119.3
C12A—C13A—H13A	119.9	C12B—C13B—H13B	119.3
C15A—C14A—C13A	121.5 (3)	C13B—C14B—C15B	120.2 (3)
C15A—C14A—H14A	119.3	C13B—C14B—H14B	119.9
C13A—C14A—H14A	119.3	C15B—C14B—H14B	119.9
C14A—C15A—C10A	118.9 (3)	C10B—C15B—C14B	119.4 (3)
C14A—C15A—H15A	120.5	C10B—C15B—H15B	120.3
C10A—C15A—H15A	120.5	C14B—C15B—H15B	120.3
C3A—N2A—C1A—N1A	−0.4 (3)	C3B—N2B—C1B—N1B	−0.4 (3)
C3A—N2A—C1A—C4A	179.5 (3)	C3B—N2B—C1B—C4B	−178.9 (3)
C2A—N1A—C1A—N2A	0.3 (3)	C2B—N1B—C1B—N2B	0.2 (3)
C2A—N1A—C1A—C4A	−179.6 (3)	C2B—N1B—C1B—C4B	178.8 (3)
C1A—N1A—C2A—C3A	−0.1 (3)	C1B—N1B—C2B—C3B	0.0 (3)
N1A—C2A—C3A—N2A	−0.2 (3)	N1B—C2B—C3B—N2B	−0.2 (3)
C1A—N2A—C3A—C2A	0.4 (3)	C1B—N2B—C3B—C2B	0.4 (3)
C5A—N3A—C4A—C1A	−179.3 (2)	C5B—N3B—C4B—C1B	−178.1 (3)
N2A—C1A—C4A—N3A	−172.7 (3)	N2B—C1B—C4B—N3B	−174.1 (3)
N1A—C1A—C4A—N3A	7.3 (4)	N1B—C1B—C4B—N3B	7.5 (4)
C4A—N3A—C5A—C6A	−111.5 (3)	C4B—N3B—C5B—C6B	−112.1 (3)
N3A—C5A—C6A—C7A	−175.5 (3)	N3B—C5B—C6B—C7B	−173.8 (3)
C5A—C6A—C7A—C8A	4.2 (5)	C5B—C6B—C7B—C8B	9.4 (5)
C5A—C6A—C7A—C11A	−176.5 (3)	C5B—C6B—C7B—C11B	−170.9 (3)
C11A—C7A—C8A—C9A	−1.6 (3)	C11B—C7B—C8B—C9B	−0.4 (3)
C6A—C7A—C8A—C9A	177.8 (3)	C6B—C7B—C8B—C9B	179.3 (3)
C7A—C8A—C9A—C10A	2.2 (3)	C7B—C8B—C9B—C10B	0.5 (3)
C8A—C9A—C10A—C15A	178.0 (3)	C8B—C9B—C10B—C15B	177.8 (3)
C8A—C9A—C10A—C11A	−2.0 (3)	C8B—C9B—C10B—C11B	−0.3 (3)
C15A—C10A—C11A—C12A	−1.4 (4)	C15B—C10B—C11B—C12B	0.4 (4)
C9A—C10A—C11A—C12A	178.6 (3)	C9B—C10B—C11B—C12B	178.8 (3)
C15A—C10A—C11A—C7A	−178.8 (3)	C15B—C10B—C11B—C7B	−178.3 (3)
C9A—C10A—C11A—C7A	1.2 (3)	C9B—C10B—C11B—C7B	0.1 (3)
C8A—C7A—C11A—C12A	−176.8 (3)	C8B—C7B—C11B—C12B	−178.2 (3)
C6A—C7A—C11A—C12A	3.8 (5)	C6B—C7B—C11B—C12B	2.0 (5)
C8A—C7A—C11A—C10A	0.2 (3)	C8B—C7B—C11B—C10B	0.2 (3)
C6A—C7A—C11A—C10A	−179.2 (3)	C6B—C7B—C11B—C10B	−179.6 (3)
C10A—C11A—C12A—C13A	1.2 (4)	C10B—C11B—C12B—C13B	−0.1 (4)
C7A—C11A—C12A—C13A	177.9 (3)	C7B—C11B—C12B—C13B	178.1 (3)
C11A—C12A—C13A—C14A	−0.9 (5)	C11B—C12B—C13B—C14B	−0.1 (5)
C12A—C13A—C14A—C15A	0.9 (5)	C12B—C13B—C14B—C15B	0.1 (5)
C13A—C14A—C15A—C10A	−1.1 (5)	C11B—C10B—C15B—C14B	−0.4 (4)
C11A—C10A—C15A—C14A	1.3 (5)	C9B—C10B—C15B—C14B	−178.3 (3)
C9A—C10A—C15A—C14A	−178.7 (3)	C13B—C14B—C15B—C10B	0.1 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N2B	0.80 (4)	2.16 (4)	2.935 (4)	162 (4)
N1B—H1B···N2Ai	0.92 (4)	2.10 (4)	3.006 (4)	170 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯N2B	0.80 (4)	2.16 (4)	2.935 (4)	162 (4)
N1B—H1B⋯N2Ai	0.92 (4)	2.10 (4)	3.006 (4)	170 (3)

Symmetry code: (i) .