N-(5-Amino-2-methyl-phen-yl)-4-(3-pyri-dyl)-pyrimidin-2-amine.

The title compound, C(16)H(15)N(5), crystallizes with two independent mol-ecules (A and B) in the asymmetric unit. The dihedral angles of the pyrimidine ring with the benzene and pyridyl rings are 22.3 (1) and 53.2 (9)°, respectively, in mol-ecule A, and 6.8 (1) and 11.6 (9)° in mol-ecule B. The crystal packing is influenced by the collective action of weak inter-molecular N-H⋯N hydrogen bonds, a π-π stacking inter-action between neighbouring pyridyl rings of mol-ecule A [centroid-centroid distance = 3.8395 (10) Å] and C-H⋯π inter-actions.

Related literature

For imatinib mesylate, see: Druker et al. (1996 ▶, 2001 ▶); Kalaycio (2004 ▶); Peggs & Mackinnon (2003 ▶). For related structures, see: Hu et al. (2006 ▶); Lynch & McClenaghan (2001 ▶); Santoni et al. (2008 ▶); Wolska et al. (2003 ▶). For bond-length data, see: Allen et al. (1987 ▶). For MOPAC Parameterized Model 3 calculation, see: Schmidt & Polik (2007 ▶).

Experimental

Crystal data

C16H15N5

M = 277.33

Triclinic,

a = 9.2242 (3) Å

b = 12.5399 (4) Å

c = 12.8594 (4) Å

α = 72.719 (3)°

β = 89.724 (3)°

γ = 77.712 (3)°

V = 1385.05 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 200 K

0.55 × 0.48 × 0.37 mm

Data collection

Oxford Diffraction Gemini R diffractometer

11476 measured reflections

5337 independent reflections

4629 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.198

S = 1.08

5337 reflections

381 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.36 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810000899/is2512sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000899/is2512Isup2.hkl

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

C16H15N5	Z = 4
Mr = 277.33	F(000) = 584
Triclinic, P1	Dx = 1.330 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 9.2242 (3) Å	Cell parameters from 8631 reflections
b = 12.5399 (4) Å	θ = 4.4–73.5°
c = 12.8594 (4) Å	µ = 0.67 mm−1
α = 72.719 (3)°	T = 200 K
β = 89.724 (3)°	Prism, yellow-orange
γ = 77.712 (3)°	0.55 × 0.48 × 0.37 mm
V = 1385.05 (8) Å3

Oxford Diffraction Gemini R diffractometer	4629 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
graphite	θmax = 73.7°, θmin = 4.4°
Detector resolution: 10.5081 pixels mm-1	h = −11→10
φ and ω scans	k = −15→15
11476 measured reflections	l = −15→15
5337 independent 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.1456P)2 + 0.1456P] where P = (Fo2 + 2Fc2)/3
5337 reflections	(Δ/σ)max = 0.008
381 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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	0.45135 (18)	1.19152 (15)	0.78047 (14)	0.0532 (4)
H1AA	0.4813	1.2472	0.7965	0.064*
H1AB	0.4989	1.1200	0.8104	0.064*
N2A	0.09164 (16)	1.06549 (11)	0.59640 (10)	0.0367 (3)
H2AB	0.0731	1.0718	0.5275	0.044*
N3A	0.00963 (15)	0.89841 (12)	0.63377 (10)	0.0351 (3)
N4A	0.09680 (14)	0.95804 (11)	0.77803 (10)	0.0315 (3)
N5A	0.22563 (16)	0.91112 (13)	1.09733 (11)	0.0402 (3)
C1A	0.14467 (17)	1.15507 (13)	0.61884 (11)	0.0325 (3)
C2A	0.27421 (17)	1.12989 (14)	0.68428 (12)	0.0354 (3)
H2AA	0.3267	1.0525	0.7136	0.043*
C3A	0.32847 (18)	1.21663 (15)	0.70762 (13)	0.0384 (4)
C4A	0.2529 (2)	1.33008 (14)	0.66004 (13)	0.0402 (4)
H4AA	0.2900	1.3908	0.6720	0.048*
C5A	0.1243 (2)	1.35351 (14)	0.59555 (13)	0.0405 (4)
H5AA	0.0740	1.4312	0.5644	0.049*
C6A	0.06427 (18)	1.26855 (14)	0.57380 (11)	0.0349 (3)
C7A	−0.0847 (2)	1.29936 (16)	0.51227 (14)	0.0449 (4)
H7AA	−0.1031	1.2322	0.4949	0.067*
H7AB	−0.0852	1.3614	0.4445	0.067*
H7AC	−0.1627	1.3245	0.5573	0.067*
C8A	0.06709 (16)	0.97057 (13)	0.67282 (11)	0.0307 (3)
C9A	−0.02004 (18)	0.80801 (14)	0.70933 (13)	0.0364 (4)
H9AA	−0.0606	0.7550	0.6856	0.044*
C10A	0.00484 (18)	0.78733 (14)	0.81973 (12)	0.0352 (3)
H10A	−0.0175	0.7222	0.8717	0.042*
C11A	0.06433 (15)	0.86674 (13)	0.85112 (12)	0.0305 (3)
C12A	0.09418 (16)	0.85691 (13)	0.96677 (11)	0.0309 (3)
C13A	0.02152 (18)	0.79443 (15)	1.05046 (13)	0.0379 (4)
H13A	−0.0485	0.7548	1.0347	0.045*
C14A	0.05232 (19)	0.79062 (15)	1.15671 (13)	0.0410 (4)
H14A	0.0043	0.7484	1.2152	0.049*
C15A	0.15462 (19)	0.84969 (15)	1.17594 (13)	0.0396 (4)
H15A	0.1758	0.8465	1.2492	0.048*
C16A	0.19464 (18)	0.91374 (14)	0.99509 (12)	0.0352 (3)
H16A	0.2441	0.9570	0.9383	0.042*
N1B	0.6390 (2)	0.87330 (16)	0.93581 (14)	0.0577 (5)
H1BA	0.7029	0.9169	0.9334	0.069*
H1BB	0.6078	0.8380	0.9988	0.069*
N2B	0.35671 (16)	0.69036 (13)	0.74824 (11)	0.0410 (3)
H2BB	0.3241	0.6949	0.6825	0.049*
N3B	0.23997 (18)	0.54289 (14)	0.79199 (12)	0.0442 (4)
N4B	0.33110 (14)	0.60433 (12)	0.93401 (11)	0.0351 (3)
N5B	0.40511 (18)	0.59479 (14)	1.25219 (12)	0.0479 (4)
C1B	0.44747 (17)	0.76724 (14)	0.74862 (13)	0.0365 (4)
C2B	0.49205 (18)	0.78610 (14)	0.84372 (13)	0.0386 (4)
H2BA	0.4574	0.7484	0.9115	0.046*
C3B	0.58759 (18)	0.86016 (15)	0.84028 (15)	0.0409 (4)
C4B	0.63588 (18)	0.91542 (15)	0.73977 (15)	0.0436 (4)
H4BA	0.7005	0.9661	0.7357	0.052*
C5B	0.58953 (19)	0.89634 (15)	0.64595 (15)	0.0439 (4)
H5BA	0.6238	0.9347	0.5783	0.053*
C6B	0.49516 (18)	0.82354 (15)	0.64661 (13)	0.0402 (4)
C7B	0.4463 (2)	0.80618 (19)	0.54245 (15)	0.0525 (5)
H7BA	0.5010	0.8444	0.4824	0.079*
H7BB	0.3395	0.8388	0.5266	0.079*
H7BC	0.4665	0.7241	0.5506	0.079*
C8B	0.30922 (17)	0.61004 (14)	0.82990 (13)	0.0351 (3)
C9B	0.1970 (3)	0.46071 (19)	0.86902 (16)	0.0539 (5)
H9BA	0.1491	0.4103	0.8469	0.065*
C10B	0.2180 (3)	0.44439 (18)	0.97932 (16)	0.0528 (5)
H10B	0.1892	0.3829	1.0323	0.063*
C11B	0.28304 (18)	0.52179 (14)	1.00929 (14)	0.0373 (4)
C12B	0.30358 (18)	0.51873 (14)	1.12446 (13)	0.0374 (4)
C13B	0.2455 (2)	0.44605 (18)	1.20945 (15)	0.0509 (5)
H13B	0.1905	0.3952	1.1954	0.061*
C14B	0.2686 (3)	0.44835 (19)	1.31517 (16)	0.0563 (5)
H14B	0.2303	0.3990	1.3747	0.068*
C15B	0.3480 (2)	0.52349 (18)	1.33216 (15)	0.0494 (4)
H15B	0.3631	0.5248	1.4048	0.059*
C16B	0.3822 (2)	0.59124 (16)	1.15134 (14)	0.0420 (4)
H16B	0.4222	0.6416	1.0937	0.050*

	U11	U22	U33	U12	U13	U23
N1A	0.0455 (8)	0.0539 (9)	0.0633 (10)	−0.0141 (7)	−0.0140 (7)	−0.0198 (8)
N2A	0.0504 (8)	0.0383 (7)	0.0242 (6)	−0.0166 (6)	−0.0026 (5)	−0.0088 (5)
N3A	0.0419 (7)	0.0404 (7)	0.0270 (6)	−0.0152 (6)	−0.0007 (5)	−0.0119 (5)
N4A	0.0344 (6)	0.0360 (7)	0.0262 (6)	−0.0104 (5)	0.0003 (5)	−0.0107 (5)
N5A	0.0437 (7)	0.0474 (8)	0.0311 (7)	−0.0121 (6)	−0.0043 (5)	−0.0129 (6)
C1A	0.0392 (8)	0.0361 (8)	0.0248 (6)	−0.0131 (6)	0.0039 (5)	−0.0100 (5)
C2A	0.0367 (8)	0.0372 (8)	0.0336 (7)	−0.0106 (6)	0.0018 (6)	−0.0109 (6)
C3A	0.0381 (8)	0.0463 (9)	0.0345 (8)	−0.0159 (7)	0.0019 (6)	−0.0132 (6)
C4A	0.0502 (9)	0.0402 (8)	0.0358 (8)	−0.0195 (7)	0.0028 (6)	−0.0130 (6)
C5A	0.0546 (10)	0.0343 (8)	0.0319 (7)	−0.0109 (7)	−0.0007 (6)	−0.0082 (6)
C6A	0.0413 (8)	0.0394 (8)	0.0238 (6)	−0.0101 (6)	0.0001 (6)	−0.0084 (6)
C7A	0.0495 (9)	0.0448 (9)	0.0381 (8)	−0.0037 (7)	−0.0097 (7)	−0.0135 (7)
C8A	0.0321 (7)	0.0344 (7)	0.0271 (7)	−0.0087 (6)	0.0005 (5)	−0.0107 (5)
C9A	0.0409 (8)	0.0419 (8)	0.0332 (8)	−0.0184 (6)	0.0025 (6)	−0.0153 (6)
C10A	0.0389 (8)	0.0396 (8)	0.0299 (7)	−0.0158 (6)	0.0035 (6)	−0.0097 (6)
C11A	0.0285 (7)	0.0364 (7)	0.0274 (7)	−0.0076 (6)	0.0016 (5)	−0.0106 (6)
C12A	0.0304 (7)	0.0350 (7)	0.0271 (7)	−0.0056 (6)	0.0003 (5)	−0.0100 (6)
C13A	0.0391 (8)	0.0466 (9)	0.0306 (8)	−0.0144 (7)	0.0032 (6)	−0.0121 (6)
C14A	0.0451 (9)	0.0497 (9)	0.0278 (8)	−0.0125 (7)	0.0073 (6)	−0.0099 (6)
C15A	0.0460 (9)	0.0457 (9)	0.0262 (7)	−0.0050 (7)	−0.0026 (6)	−0.0132 (6)
C16A	0.0379 (8)	0.0411 (8)	0.0281 (7)	−0.0123 (6)	0.0003 (6)	−0.0103 (6)
N1B	0.0666 (11)	0.0661 (11)	0.0539 (9)	−0.0375 (9)	0.0047 (8)	−0.0222 (8)
N2B	0.0444 (7)	0.0495 (8)	0.0332 (7)	−0.0205 (6)	0.0025 (5)	−0.0117 (6)
N3B	0.0504 (8)	0.0514 (8)	0.0397 (7)	−0.0241 (7)	0.0054 (6)	−0.0182 (6)
N4B	0.0319 (6)	0.0393 (7)	0.0362 (7)	−0.0123 (5)	0.0042 (5)	−0.0118 (5)
N5B	0.0513 (9)	0.0535 (9)	0.0423 (8)	−0.0134 (7)	−0.0011 (6)	−0.0183 (7)
C1B	0.0322 (7)	0.0371 (8)	0.0401 (8)	−0.0099 (6)	0.0039 (6)	−0.0101 (6)
C2B	0.0376 (8)	0.0407 (8)	0.0397 (8)	−0.0139 (7)	0.0062 (6)	−0.0117 (7)
C3B	0.0355 (8)	0.0400 (8)	0.0490 (9)	−0.0108 (6)	0.0017 (7)	−0.0145 (7)
C4B	0.0354 (8)	0.0401 (8)	0.0570 (10)	−0.0152 (7)	0.0061 (7)	−0.0123 (7)
C5B	0.0384 (8)	0.0433 (9)	0.0461 (9)	−0.0110 (7)	0.0081 (7)	−0.0067 (7)
C6B	0.0362 (8)	0.0424 (9)	0.0392 (8)	−0.0084 (7)	0.0032 (6)	−0.0084 (7)
C7B	0.0612 (11)	0.0611 (11)	0.0365 (9)	−0.0258 (9)	0.0064 (8)	−0.0079 (8)
C8B	0.0314 (7)	0.0384 (8)	0.0374 (8)	−0.0103 (6)	0.0033 (6)	−0.0127 (6)
C9B	0.0702 (12)	0.0605 (11)	0.0472 (10)	−0.0402 (10)	0.0110 (9)	−0.0229 (9)
C10B	0.0721 (13)	0.0568 (11)	0.0424 (9)	−0.0398 (10)	0.0124 (8)	−0.0164 (8)
C11B	0.0350 (8)	0.0407 (8)	0.0383 (8)	−0.0121 (6)	0.0061 (6)	−0.0124 (6)
C12B	0.0357 (8)	0.0403 (8)	0.0376 (8)	−0.0093 (6)	0.0047 (6)	−0.0132 (7)
C13B	0.0584 (11)	0.0587 (11)	0.0436 (10)	−0.0277 (9)	0.0129 (8)	−0.0176 (8)
C14B	0.0692 (13)	0.0637 (12)	0.0393 (9)	−0.0244 (10)	0.0153 (8)	−0.0140 (8)
C15B	0.0547 (10)	0.0569 (11)	0.0365 (9)	−0.0077 (8)	0.0032 (7)	−0.0174 (8)
C16B	0.0441 (9)	0.0460 (9)	0.0379 (8)	−0.0145 (7)	0.0023 (7)	−0.0125 (7)

N1A—C3A	1.394 (2)	N1B—C3B	1.386 (2)
N1A—H1AA	0.8800	N1B—H1BA	0.8800
N1A—H1AB	0.8800	N1B—H1BB	0.8800
N2A—C8A	1.3606 (19)	N2B—C8B	1.365 (2)
N2A—C1A	1.4186 (19)	N2B—C1B	1.406 (2)
N2A—H2AB	0.8800	N2B—H2BB	0.8800
N3A—C9A	1.334 (2)	N3B—C9B	1.328 (2)
N3A—C8A	1.3522 (19)	N3B—C8B	1.353 (2)
N4A—C11A	1.3371 (19)	N4B—C8B	1.333 (2)
N4A—C8A	1.3377 (18)	N4B—C11B	1.342 (2)
N5A—C16A	1.336 (2)	N5B—C16B	1.330 (2)
N5A—C15A	1.338 (2)	N5B—C15B	1.336 (3)
C1A—C2A	1.388 (2)	C1B—C2B	1.392 (2)
C1A—C6A	1.406 (2)	C1B—C6B	1.410 (2)
C2A—C3A	1.397 (2)	C2B—C3B	1.402 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.396 (2)	C3B—C4B	1.394 (2)
C4A—C5A	1.378 (2)	C4B—C5B	1.384 (3)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.396 (2)	C5B—C6B	1.387 (2)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.505 (2)	C6B—C7B	1.505 (2)
C7A—H7AA	0.9800	C7B—H7BA	0.9800
C7A—H7AB	0.9800	C7B—H7BB	0.9800
C7A—H7AC	0.9800	C7B—H7BC	0.9800
C9A—C10A	1.376 (2)	C9B—C10B	1.380 (3)
C9A—H9AA	0.9500	C9B—H9BA	0.9500
C10A—C11A	1.389 (2)	C10B—C11B	1.387 (2)
C10A—H10A	0.9500	C10B—H10B	0.9500
C11A—C12A	1.4776 (19)	C11B—C12B	1.482 (2)
C12A—C13A	1.392 (2)	C12B—C13B	1.387 (2)
C12A—C16A	1.392 (2)	C12B—C16B	1.394 (2)
C13A—C14A	1.382 (2)	C13B—C14B	1.387 (3)
C13A—H13A	0.9500	C13B—H13B	0.9500
C14A—C15A	1.382 (2)	C14B—C15B	1.375 (3)
C14A—H14A	0.9500	C14B—H14B	0.9500
C15A—H15A	0.9500	C15B—H15B	0.9500
C16A—H16A	0.9500	C16B—H16B	0.9500
C3A—N1A—H1AA	120.0	C3B—N1B—H1BA	120.0
C3A—N1A—H1AB	120.0	C3B—N1B—H1BB	120.0
H1AA—N1A—H1AB	120.0	H1BA—N1B—H1BB	120.0
C8A—N2A—C1A	125.27 (12)	C8B—N2B—C1B	132.56 (13)
C8A—N2A—H2AB	117.4	C8B—N2B—H2BB	113.7
C1A—N2A—H2AB	117.4	C1B—N2B—H2BB	113.7
C9A—N3A—C8A	115.26 (12)	C9B—N3B—C8B	114.62 (14)
C11A—N4A—C8A	116.85 (13)	C8B—N4B—C11B	116.88 (14)
C16A—N5A—C15A	117.00 (14)	C16B—N5B—C15B	116.92 (16)
C2A—C1A—C6A	121.09 (14)	C2B—C1B—N2B	122.80 (14)
C2A—C1A—N2A	119.94 (14)	C2B—C1B—C6B	120.89 (15)
C6A—C1A—N2A	118.97 (14)	N2B—C1B—C6B	116.30 (14)
C1A—C2A—C3A	120.97 (15)	C1B—C2B—C3B	120.59 (15)
C1A—C2A—H2AA	119.5	C1B—C2B—H2BA	119.7
C3A—C2A—H2AA	119.5	C3B—C2B—H2BA	119.7
N1A—C3A—C4A	120.05 (15)	N1B—C3B—C4B	120.74 (16)
N1A—C3A—C2A	121.35 (16)	N1B—C3B—C2B	120.41 (16)
C4A—C3A—C2A	118.55 (14)	C4B—C3B—C2B	118.76 (16)
C5A—C4A—C3A	119.66 (15)	C5B—C4B—C3B	119.87 (15)
C5A—C4A—H4AA	120.2	C5B—C4B—H4BA	120.1
C3A—C4A—H4AA	120.2	C3B—C4B—H4BA	120.1
C4A—C5A—C6A	123.15 (15)	C4B—C5B—C6B	122.78 (16)
C4A—C5A—H5AA	118.4	C4B—C5B—H5BA	118.6
C6A—C5A—H5AA	118.4	C6B—C5B—H5BA	118.6
C5A—C6A—C1A	116.50 (14)	C5B—C6B—C1B	117.11 (16)
C5A—C6A—C7A	120.24 (15)	C5B—C6B—C7B	121.02 (15)
C1A—C6A—C7A	123.11 (14)	C1B—C6B—C7B	121.86 (15)
C6A—C7A—H7AA	109.5	C6B—C7B—H7BA	109.5
C6A—C7A—H7AB	109.5	C6B—C7B—H7BB	109.5
H7AA—C7A—H7AB	109.5	H7BA—C7B—H7BB	109.5
C6A—C7A—H7AC	109.5	C6B—C7B—H7BC	109.5
H7AA—C7A—H7AC	109.5	H7BA—C7B—H7BC	109.5
H7AB—C7A—H7AC	109.5	H7BB—C7B—H7BC	109.5
N4A—C8A—N3A	125.95 (14)	N4B—C8B—N3B	126.65 (15)
N4A—C8A—N2A	118.49 (13)	N4B—C8B—N2B	120.66 (14)
N3A—C8A—N2A	115.53 (12)	N3B—C8B—N2B	112.68 (14)
N3A—C9A—C10A	123.62 (14)	N3B—C9B—C10B	123.72 (16)
N3A—C9A—H9AA	118.2	N3B—C9B—H9BA	118.1
C10A—C9A—H9AA	118.2	C10B—C9B—H9BA	118.1
C9A—C10A—C11A	116.47 (14)	C9B—C10B—C11B	116.98 (16)
C9A—C10A—H10A	121.8	C9B—C10B—H10B	121.5
C11A—C10A—H10A	121.8	C11B—C10B—H10B	121.5
N4A—C11A—C10A	121.83 (13)	N4B—C11B—C10B	121.01 (15)
N4A—C11A—C12A	115.68 (13)	N4B—C11B—C12B	116.35 (14)
C10A—C11A—C12A	122.49 (14)	C10B—C11B—C12B	122.65 (15)
C13A—C12A—C16A	117.58 (14)	C13B—C12B—C16B	117.07 (15)
C13A—C12A—C11A	122.18 (14)	C13B—C12B—C11B	122.48 (15)
C16A—C12A—C11A	120.21 (13)	C16B—C12B—C11B	120.45 (15)
C14A—C13A—C12A	119.29 (15)	C12B—C13B—C14B	119.26 (18)
C14A—C13A—H13A	120.4	C12B—C13B—H13B	120.4
C12A—C13A—H13A	120.4	C14B—C13B—H13B	120.4
C13A—C14A—C15A	118.45 (15)	C15B—C14B—C13B	118.68 (18)
C13A—C14A—H14A	120.8	C15B—C14B—H14B	120.7
C15A—C14A—H14A	120.8	C13B—C14B—H14B	120.7
N5A—C15A—C14A	123.75 (14)	N5B—C15B—C14B	123.59 (16)
N5A—C15A—H15A	118.1	N5B—C15B—H15B	118.2
C14A—C15A—H15A	118.1	C14B—C15B—H15B	118.2
N5A—C16A—C12A	123.93 (14)	N5B—C16B—C12B	124.47 (16)
N5A—C16A—H16A	118.0	N5B—C16B—H16B	117.8
C12A—C16A—H16A	118.0	C12B—C16B—H16B	117.8
C8A—N2A—C1A—C2A	53.0 (2)	C8B—N2B—C1B—C2B	−9.9 (3)
C8A—N2A—C1A—C6A	−127.07 (16)	C8B—N2B—C1B—C6B	168.66 (17)
C6A—C1A—C2A—C3A	0.2 (2)	N2B—C1B—C2B—C3B	177.37 (15)
N2A—C1A—C2A—C3A	−179.91 (14)	C6B—C1B—C2B—C3B	−1.1 (3)
C1A—C2A—C3A—N1A	174.58 (15)	C1B—C2B—C3B—N1B	−176.01 (16)
C1A—C2A—C3A—C4A	−2.6 (2)	C1B—C2B—C3B—C4B	0.6 (3)
N1A—C3A—C4A—C5A	−174.45 (16)	N1B—C3B—C4B—C5B	176.50 (17)
C2A—C3A—C4A—C5A	2.8 (2)	C2B—C3B—C4B—C5B	−0.1 (3)
C3A—C4A—C5A—C6A	−0.5 (3)	C3B—C4B—C5B—C6B	0.1 (3)
C4A—C5A—C6A—C1A	−1.9 (2)	C4B—C5B—C6B—C1B	−0.5 (3)
C4A—C5A—C6A—C7A	173.70 (16)	C4B—C5B—C6B—C7B	179.38 (17)
C2A—C1A—C6A—C5A	2.0 (2)	C2B—C1B—C6B—C5B	1.0 (2)
N2A—C1A—C6A—C5A	−177.91 (13)	N2B—C1B—C6B—C5B	−177.55 (14)
C2A—C1A—C6A—C7A	−173.39 (14)	C2B—C1B—C6B—C7B	−178.88 (16)
N2A—C1A—C6A—C7A	6.7 (2)	N2B—C1B—C6B—C7B	2.6 (2)
C11A—N4A—C8A—N3A	−1.2 (2)	C11B—N4B—C8B—N3B	1.8 (2)
C11A—N4A—C8A—N2A	176.72 (13)	C11B—N4B—C8B—N2B	−179.01 (14)
C9A—N3A—C8A—N4A	0.7 (2)	C9B—N3B—C8B—N4B	−3.2 (3)
C9A—N3A—C8A—N2A	−177.29 (13)	C9B—N3B—C8B—N2B	177.55 (17)
C1A—N2A—C8A—N4A	−1.1 (2)	C1B—N2B—C8B—N4B	9.8 (3)
C1A—N2A—C8A—N3A	176.99 (14)	C1B—N2B—C8B—N3B	−170.97 (17)
C8A—N3A—C9A—C10A	0.0 (2)	C8B—N3B—C9B—C10B	0.9 (3)
N3A—C9A—C10A—C11A	−0.1 (2)	N3B—C9B—C10B—C11B	2.4 (3)
C8A—N4A—C11A—C10A	1.0 (2)	C8B—N4B—C11B—C10B	1.9 (2)
C8A—N4A—C11A—C12A	−178.27 (12)	C8B—N4B—C11B—C12B	−178.07 (13)
C9A—C10A—C11A—N4A	−0.5 (2)	C9B—C10B—C11B—N4B	−3.9 (3)
C9A—C10A—C11A—C12A	178.78 (14)	C9B—C10B—C11B—C12B	176.12 (18)
N4A—C11A—C12A—C13A	156.70 (14)	N4B—C11B—C12B—C13B	173.11 (16)
C10A—C11A—C12A—C13A	−22.6 (2)	C10B—C11B—C12B—C13B	−6.9 (3)
N4A—C11A—C12A—C16A	−21.4 (2)	N4B—C11B—C12B—C16B	−6.2 (2)
C10A—C11A—C12A—C16A	159.27 (15)	C10B—C11B—C12B—C16B	173.81 (18)
C16A—C12A—C13A—C14A	−0.5 (2)	C16B—C12B—C13B—C14B	−0.3 (3)
C11A—C12A—C13A—C14A	−178.66 (14)	C11B—C12B—C13B—C14B	−179.66 (17)
C12A—C13A—C14A—C15A	0.2 (3)	C12B—C13B—C14B—C15B	0.4 (3)
C16A—N5A—C15A—C14A	−0.4 (3)	C16B—N5B—C15B—C14B	0.0 (3)
C13A—C14A—C15A—N5A	0.3 (3)	C13B—C14B—C15B—N5B	−0.2 (3)
C15A—N5A—C16A—C12A	0.0 (2)	C15B—N5B—C16B—C12B	0.0 (3)
C13A—C12A—C16A—N5A	0.4 (2)	C13B—C12B—C16B—N5B	0.2 (3)
C11A—C12A—C16A—N5A	178.63 (14)	C11B—C12B—C16B—N5B	179.52 (16)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1AA···N5Bi	0.88	2.36	3.154 (2)	151
N2A—H2AB···N3Aii	0.88	2.11	2.9815 (17)	170
N1B—H1BA···N5Ai	0.88	2.31	3.130 (2)	155
C2A—H2AA···Cg3	0.95	2.87	3.7834 (19)	162
C14A—H14A···Cg2iii	0.95	2.64	3.4709 (18)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1AA⋯N5Bi	0.88	2.36	3.154 (2)	151
N2A—H2AB⋯N3Aii	0.88	2.11	2.9815 (17)	170
N1B—H1BA⋯N5Ai	0.88	2.31	3.130 (2)	155
C2A—H2AA⋯Cg3	0.95	2.87	3.7834 (19)	162
C14A—H14A⋯Cg2iii	0.95	2.64	3.4709 (18)	146

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg3 are centroids of the C1A–C6A and C1B–C6B rings, respectively.