Naphthalene-1,8-di-amine-2-(pyrimidin-2-yl)-1H-perimidine (2/1).

In the title adduct, C15H10N4·2C10H10N2, the pyrimidine ring is nearly co-planar with the heteroatomic perimidine ring, as indicated dihedral angle between their mean planes of 3.21 (11)°. The di-aminona-phthalene mol-ecules are slightly twisted [dihedral angles = 4.2 (2) and 3.0 (2)°] because of the steric encumbrance of NH2 groups. The perimidine and di-aminona-phthalene mol-ecules are linked by N-H⋯N hydrogen bonds, forming an R (4) 4(12) graph-set motif across an inversion center. In the crystal, alternating layers of the perimidine and di-aminona-phthalene mol-ecules are formed along [100]. In the perimidine layer, mol-ecules are π-π stacked along the c-axis direction with an inter-plane separation of approximately 3.4 Å.

Related literature

For the coordination properties of perimidines, see: Morita et al. (2003 ▶); Cucciolito et al. (2013 ▶). For structural data on perimidines, see: Foces-Foces et al. (1993 ▶); Llamas-Saiz et al. (1995 ▶); Filatova et al. (2000 ▶); Murata et al. (2006 ▶); Smellie et al. (2011 ▶). For structural data on naphthalene-1,8-di­amine, see: Llamas-Saiz et al. (1991 ▶); Basaran et al. (1993 ▶); Batsanov et al. (2001 ▶). For N-rich aromatic heterocycles in organic electronics and photonics, see: Goswami et al. (2010 ▶); Carella et al. (2012 ▶); Centore et al. (2012 ▶). For a general survey of hydrogen bonding in crystals, see: Desiraju & Steiner (1999 ▶); Steiner (2002 ▶). For hydrogen-bonding patterns in nitro­gen-containing heterocycles, see: Centore et al. (2013a ▶,b ▶).

Experimental

Crystal data

C15H10N4·2C10H10N2

M = 562.67

Monoclinic,

a = 17.083 (2) Å

b = 12.139 (3) Å

c = 13.597 (2) Å

β = 90.76 (1)°

V = 2819.4 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 173 K

0.50 × 0.45 × 0.10 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.960, T max = 0.992

22722 measured reflections

5184 independent reflections

2799 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.142

S = 1.06

5184 reflections

415 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.18 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016796/go2093sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016796/go2093Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016796/go2093Isup3.cml

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

C15H10N4·2C10H10N2	F(000) = 1184
Mr = 562.67	Dx = 1.326 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 126 reflections
a = 17.083 (2) Å	θ = 3.4–21.8°
b = 12.139 (3) Å	µ = 0.08 mm−1
c = 13.597 (2) Å	T = 173 K
β = 90.76 (1)°	Block, orange
V = 2819.4 (9) Å3	0.50 × 0.45 × 0.10 mm
Z = 4

Bruker–Nonius KappaCCD diffractometer	5184 independent reflections
Radiation source: normal-focus sealed tube	2799 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.080
Detector resolution: 9 pixels mm-1	θmax = 25.4°, θmin = 3.2°
CCD rotation images, thick slices scans	h = −20→20
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→14
Tmin = 0.960, Tmax = 0.992	l = −16→16
22722 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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.142	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0402P)2 + 1.5806P] where P = (Fo2 + 2Fc2)/3
5184 reflections	(Δ/σ)max < 0.001
415 parameters	Δρmax = 0.19 e Å−3
2 restraints	Δρmin = −0.18 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
N1	−0.06299 (14)	0.0273 (2)	0.36212 (17)	0.0276 (6)
H1	−0.0848 (16)	−0.037 (2)	0.365 (2)	0.033*
N2	0.05732 (13)	0.12080 (19)	0.37659 (16)	0.0269 (6)
N3	0.13410 (14)	−0.0767 (2)	0.38241 (18)	0.0352 (6)
N4	0.00939 (14)	−0.16518 (19)	0.37372 (17)	0.0309 (6)
N1A	0.17020 (18)	0.3184 (3)	0.7032 (2)	0.0500 (9)
H1C	0.1574 (19)	0.358 (3)	0.753 (3)	0.060*
H1D	0.1615 (19)	0.244 (3)	0.7159 (19)	0.060*
N2A	0.16490 (15)	0.1606 (2)	0.5578 (2)	0.0400 (7)
H2C	0.1462 (18)	0.126 (3)	0.502 (2)	0.048*
H2D	0.1347 (18)	0.216 (3)	0.5700 (19)	0.048*
N1B	0.44606 (19)	0.9546 (3)	0.6366 (2)	0.0624 (10)
H1E	0.430 (2)	1.011 (3)	0.588 (3)	0.075*
H1F	0.4405 (19)	0.878 (3)	0.615 (2)	0.075*
N2B	0.48654 (19)	0.7540 (3)	0.7084 (3)	0.0634 (10)
H2E	0.5269 (19)	0.805 (3)	0.702 (3)	0.076*
H2F	0.509 (2)	0.686 (3)	0.709 (3)	0.076*
C1	−0.10821 (16)	0.1228 (2)	0.3582 (2)	0.0270 (7)
C2	−0.18822 (16)	0.1208 (3)	0.3468 (2)	0.0334 (7)
H2	−0.2158	0.0532	0.3403	0.040*
C3	−0.22799 (18)	0.2222 (3)	0.3449 (2)	0.0407 (8)
H3	−0.2833	0.2224	0.3367	0.049*
C4	−0.18985 (19)	0.3200 (3)	0.3547 (2)	0.0391 (8)
H4	−0.2190	0.3867	0.3543	0.047*
C5	−0.10814 (17)	0.3240 (2)	0.3652 (2)	0.0299 (7)
C6	−0.0637 (2)	0.4223 (2)	0.3748 (2)	0.0380 (8)
H6	−0.0895	0.4916	0.3748	0.046*
C7	0.0159 (2)	0.4181 (2)	0.3840 (2)	0.0392 (8)
H7	0.0444	0.4849	0.3906	0.047*
C8	0.05660 (18)	0.3185 (2)	0.3841 (2)	0.0343 (8)
H8	0.1121	0.3181	0.3898	0.041*
C9	0.01606 (17)	0.2209 (2)	0.3757 (2)	0.0266 (7)
C10	−0.06663 (16)	0.2226 (2)	0.36614 (19)	0.0256 (7)
C11	0.01603 (16)	0.0311 (2)	0.3711 (2)	0.0244 (7)
C12	0.05592 (16)	−0.0776 (2)	0.37559 (19)	0.0253 (7)
C13	0.16700 (19)	−0.1763 (3)	0.3871 (2)	0.0416 (8)
H13	0.2225	−0.1807	0.3915	0.050*
C14	0.12521 (19)	−0.2720 (3)	0.3860 (2)	0.0366 (8)
H14	0.1502	−0.3418	0.3899	0.044*
C15	0.04540 (19)	−0.2627 (2)	0.3789 (2)	0.0347 (8)
H15	0.0146	−0.3278	0.3776	0.042*
C1A	0.24650 (19)	0.3402 (3)	0.6713 (2)	0.0370 (8)
C2A	0.2866 (2)	0.4285 (3)	0.7099 (2)	0.0491 (10)
H2A	0.2626	0.4724	0.7588	0.059*
C3A	0.3619 (2)	0.4554 (3)	0.6791 (3)	0.0533 (10)
H3A	0.3874	0.5183	0.7058	0.064*
C4A	0.39903 (19)	0.3927 (3)	0.6114 (3)	0.0454 (9)
H4A	0.4507	0.4110	0.5921	0.054*
C5A	0.36083 (17)	0.3002 (2)	0.5698 (2)	0.0320 (7)
C6A	0.40047 (18)	0.2335 (3)	0.5023 (2)	0.0395 (8)
H6A	0.4532	0.2496	0.4864	0.047*
C7A	0.36393 (19)	0.1463 (3)	0.4595 (2)	0.0419 (9)
H7A	0.3919	0.1002	0.4157	0.050*
C8A	0.28593 (18)	0.1239 (3)	0.4792 (2)	0.0374 (8)
H8A	0.2610	0.0635	0.4472	0.045*
C9A	0.24415 (16)	0.1870 (2)	0.5438 (2)	0.0293 (7)
C10A	0.28182 (16)	0.2759 (2)	0.5957 (2)	0.0285 (7)
C1B	0.40270 (18)	0.9666 (3)	0.7235 (3)	0.0426 (9)
C2B	0.3652 (2)	1.0638 (3)	0.7392 (3)	0.0549 (10)
H2B	0.3690	1.1203	0.6912	0.066*
C3B	0.3216 (2)	1.0833 (3)	0.8226 (3)	0.0632 (12)
H3B	0.2972	1.1529	0.8315	0.076*
C4B	0.3137 (2)	1.0033 (3)	0.8918 (3)	0.0563 (11)
H4B	0.2829	1.0162	0.9482	0.068*
C5B	0.35172 (18)	0.9003 (3)	0.8793 (3)	0.0409 (9)
C6B	0.3421 (2)	0.8162 (4)	0.9495 (3)	0.0567 (10)
H6B	0.3122	0.8297	1.0067	0.068*
C7B	0.3754 (2)	0.7156 (3)	0.9355 (3)	0.0601 (11)
H7B	0.3661	0.6581	0.9813	0.072*
C8B	0.4223 (2)	0.6962 (3)	0.8556 (3)	0.0514 (10)
H8B	0.4454	0.6256	0.8478	0.062*
C9B	0.43639 (18)	0.7761 (3)	0.7875 (3)	0.0406 (8)
C10B	0.39817 (17)	0.8811 (3)	0.7954 (2)	0.0344 (8)

	U11	U22	U33	U12	U13	U23
N1	0.0295 (15)	0.0195 (14)	0.0338 (15)	−0.0026 (11)	0.0021 (12)	−0.0003 (12)
N2	0.0309 (14)	0.0224 (14)	0.0274 (14)	−0.0013 (11)	0.0025 (11)	0.0024 (11)
N3	0.0298 (15)	0.0333 (16)	0.0423 (17)	0.0030 (12)	−0.0031 (12)	−0.0014 (12)
N4	0.0376 (15)	0.0196 (14)	0.0356 (15)	0.0006 (12)	0.0062 (12)	0.0015 (11)
N1A	0.058 (2)	0.049 (2)	0.044 (2)	0.0175 (17)	0.0180 (16)	0.0009 (15)
N2A	0.0279 (16)	0.0462 (19)	0.0457 (18)	−0.0023 (13)	−0.0014 (13)	0.0048 (14)
N1B	0.067 (2)	0.070 (2)	0.050 (2)	−0.0128 (19)	−0.0006 (18)	0.0161 (18)
N2B	0.054 (2)	0.064 (3)	0.072 (2)	0.0110 (17)	0.0032 (19)	−0.018 (2)
C1	0.0333 (18)	0.0265 (17)	0.0213 (16)	0.0010 (14)	0.0027 (13)	0.0027 (13)
C2	0.0289 (18)	0.0361 (19)	0.0351 (19)	0.0000 (15)	−0.0007 (14)	0.0012 (15)
C3	0.0321 (19)	0.052 (2)	0.038 (2)	0.0099 (17)	0.0003 (15)	0.0036 (17)
C4	0.045 (2)	0.038 (2)	0.0336 (19)	0.0172 (17)	0.0032 (16)	0.0048 (16)
C5	0.042 (2)	0.0270 (17)	0.0202 (16)	0.0066 (15)	0.0034 (14)	−0.0010 (13)
C6	0.063 (2)	0.0218 (17)	0.0294 (19)	0.0078 (16)	0.0017 (17)	0.0026 (14)
C7	0.055 (2)	0.0240 (18)	0.038 (2)	−0.0063 (16)	−0.0025 (17)	−0.0004 (15)
C8	0.0406 (19)	0.0282 (18)	0.0340 (19)	−0.0022 (15)	−0.0011 (15)	0.0007 (14)
C9	0.0389 (18)	0.0211 (16)	0.0199 (16)	−0.0015 (14)	0.0016 (14)	−0.0012 (13)
C10	0.0341 (18)	0.0263 (17)	0.0166 (15)	−0.0006 (14)	0.0015 (13)	−0.0019 (12)
C11	0.0280 (17)	0.0256 (17)	0.0198 (16)	−0.0006 (14)	0.0031 (13)	−0.0004 (13)
C12	0.0331 (18)	0.0282 (17)	0.0146 (16)	−0.0002 (14)	0.0028 (13)	−0.0010 (13)
C13	0.0386 (19)	0.044 (2)	0.042 (2)	0.0117 (18)	−0.0039 (16)	−0.0006 (16)
C14	0.050 (2)	0.0298 (19)	0.0299 (19)	0.0106 (16)	0.0010 (16)	0.0010 (14)
C15	0.048 (2)	0.0226 (18)	0.0336 (19)	−0.0010 (15)	0.0067 (16)	0.0005 (14)
C1A	0.045 (2)	0.036 (2)	0.0293 (19)	0.0145 (16)	−0.0003 (16)	0.0048 (15)
C2A	0.079 (3)	0.036 (2)	0.032 (2)	0.017 (2)	−0.0075 (19)	−0.0048 (17)
C3A	0.071 (3)	0.037 (2)	0.051 (2)	−0.008 (2)	−0.029 (2)	−0.0005 (19)
C4A	0.040 (2)	0.047 (2)	0.048 (2)	−0.0062 (17)	−0.0169 (17)	0.0059 (18)
C5A	0.0319 (18)	0.0334 (19)	0.0305 (18)	−0.0006 (14)	−0.0079 (14)	0.0039 (14)
C6A	0.0281 (18)	0.051 (2)	0.040 (2)	−0.0026 (16)	0.0022 (16)	0.0068 (17)
C7A	0.040 (2)	0.050 (2)	0.036 (2)	0.0082 (17)	0.0068 (16)	−0.0053 (16)
C8A	0.046 (2)	0.0325 (19)	0.0333 (19)	−0.0042 (16)	−0.0010 (16)	−0.0041 (15)
C9A	0.0284 (17)	0.0299 (17)	0.0295 (18)	−0.0015 (14)	−0.0035 (14)	0.0068 (14)
C10A	0.0296 (17)	0.0302 (17)	0.0256 (17)	0.0039 (13)	−0.0046 (14)	0.0078 (14)
C1B	0.0345 (19)	0.044 (2)	0.049 (2)	−0.0091 (17)	−0.0123 (17)	0.0052 (18)
C2B	0.059 (2)	0.041 (2)	0.065 (3)	−0.0044 (19)	−0.022 (2)	0.004 (2)
C3B	0.065 (3)	0.036 (2)	0.088 (3)	0.009 (2)	−0.028 (2)	−0.015 (2)
C4B	0.047 (2)	0.063 (3)	0.059 (3)	0.002 (2)	−0.0093 (19)	−0.027 (2)
C5B	0.0336 (19)	0.044 (2)	0.045 (2)	−0.0066 (16)	−0.0081 (17)	−0.0036 (17)
C6B	0.044 (2)	0.079 (3)	0.047 (2)	−0.011 (2)	−0.0019 (18)	0.007 (2)
C7B	0.050 (2)	0.062 (3)	0.067 (3)	−0.022 (2)	−0.017 (2)	0.031 (2)
C8B	0.045 (2)	0.038 (2)	0.071 (3)	−0.0052 (17)	−0.023 (2)	0.005 (2)
C9B	0.0308 (18)	0.044 (2)	0.047 (2)	−0.0023 (16)	−0.0101 (16)	−0.0069 (18)
C10B	0.0308 (17)	0.0348 (19)	0.038 (2)	−0.0050 (15)	−0.0076 (15)	−0.0021 (15)

N1—C11	1.355 (3)	C13—C14	1.364 (4)
N1—C1	1.393 (3)	C13—H13	0.9500
N1—H1	0.86 (3)	C14—C15	1.370 (4)
N2—C11	1.299 (3)	C14—H14	0.9500
N2—C9	1.404 (3)	C15—H15	0.9500
N3—C13	1.334 (4)	C1A—C2A	1.373 (4)
N3—C12	1.338 (3)	C1A—C10A	1.431 (4)
N4—C12	1.328 (3)	C2A—C3A	1.396 (5)
N4—C15	1.335 (3)	C2A—H2A	0.9500
N1A—C1A	1.404 (4)	C3A—C4A	1.358 (5)
N1A—H1C	0.87 (3)	C3A—H3A	0.9500
N1A—H1D	0.93 (3)	C4A—C5A	1.413 (4)
N2A—C9A	1.407 (4)	C4A—H4A	0.9500
N2A—H2C	0.92 (3)	C5A—C6A	1.405 (4)
N2A—H2D	0.87 (3)	C5A—C10A	1.430 (4)
N1B—C1B	1.411 (4)	C6A—C7A	1.356 (4)
N1B—H1E	0.98 (4)	C6A—H6A	0.9500
N1B—H1F	0.98 (4)	C7A—C8A	1.390 (4)
N2B—C9B	1.410 (4)	C7A—H7A	0.9500
N2B—H2E	0.93 (4)	C8A—C9A	1.374 (4)
N2B—H2F	0.91 (4)	C8A—H8A	0.9500
C1—C2	1.374 (4)	C9A—C10A	1.436 (4)
C1—C10	1.408 (4)	C1B—C2B	1.361 (5)
C2—C3	1.406 (4)	C1B—C10B	1.428 (4)
C2—H2	0.9500	C2B—C3B	1.385 (5)
C3—C4	1.360 (4)	C2B—H2B	0.9500
C3—H3	0.9500	C3B—C4B	1.360 (5)
C4—C5	1.402 (4)	C3B—H3B	0.9500
C4—H4	0.9500	C4B—C5B	1.420 (5)
C5—C6	1.420 (4)	C4B—H4B	0.9500
C5—C10	1.421 (4)	C5B—C6B	1.408 (5)
C6—C7	1.364 (4)	C5B—C10B	1.417 (4)
C6—H6	0.9500	C6B—C7B	1.361 (5)
C7—C8	1.395 (4)	C6B—H6B	0.9500
C7—H7	0.9500	C7B—C8B	1.380 (5)
C8—C9	1.377 (4)	C7B—H7B	0.9500
C8—H8	0.9500	C8B—C9B	1.363 (5)
C9—C10	1.417 (4)	C8B—H8B	0.9500
C11—C12	1.486 (4)	C9B—C10B	1.437 (4)
C11—N1—C1	121.8 (2)	C14—C15—H15	118.8
C11—N1—H1	117.2 (19)	C2A—C1A—N1A	119.3 (3)
C1—N1—H1	120.7 (19)	C2A—C1A—C10A	119.2 (3)
C11—N2—C9	116.9 (2)	N1A—C1A—C10A	121.4 (3)
C13—N3—C12	114.6 (3)	C1A—C2A—C3A	121.6 (3)
C12—N4—C15	115.7 (3)	C1A—C2A—H2A	119.2
C1A—N1A—H1C	113 (2)	C3A—C2A—H2A	119.2
C1A—N1A—H1D	113 (2)	C4A—C3A—C2A	120.9 (3)
H1C—N1A—H1D	111 (3)	C4A—C3A—H3A	119.6
C9A—N2A—H2C	108.4 (19)	C2A—C3A—H3A	119.6
C9A—N2A—H2D	115 (2)	C3A—C4A—C5A	119.9 (3)
H2C—N2A—H2D	108 (3)	C3A—C4A—H4A	120.0
C1B—N1B—H1E	110 (2)	C5A—C4A—H4A	120.0
C1B—N1B—H1F	108 (2)	C6A—C5A—C4A	119.7 (3)
H1E—N1B—H1F	115 (3)	C6A—C5A—C10A	120.4 (3)
C9B—N2B—H2E	113 (2)	C4A—C5A—C10A	119.9 (3)
C9B—N2B—H2F	115 (2)	C7A—C6A—C5A	120.5 (3)
H2E—N2B—H2F	108 (3)	C7A—C6A—H6A	119.8
C2—C1—N1	122.7 (3)	C5A—C6A—H6A	119.8
C2—C1—C10	121.6 (3)	C6A—C7A—C8A	120.5 (3)
N1—C1—C10	115.7 (3)	C6A—C7A—H7A	119.7
C1—C2—C3	117.8 (3)	C8A—C7A—H7A	119.7
C1—C2—H2	121.1	C9A—C8A—C7A	121.4 (3)
C3—C2—H2	121.1	C9A—C8A—H8A	119.3
C4—C3—C2	122.1 (3)	C7A—C8A—H8A	119.3
C4—C3—H3	118.9	C8A—C9A—N2A	117.9 (3)
C2—C3—H3	118.9	C8A—C9A—C10A	120.0 (3)
C3—C4—C5	121.0 (3)	N2A—C9A—C10A	122.1 (3)
C3—C4—H4	119.5	C5A—C10A—C1A	118.2 (3)
C5—C4—H4	119.5	C5A—C10A—C9A	116.9 (3)
C4—C5—C6	124.7 (3)	C1A—C10A—C9A	124.9 (3)
C4—C5—C10	117.8 (3)	C2B—C1B—N1B	118.3 (3)
C6—C5—C10	117.5 (3)	C2B—C1B—C10B	119.5 (3)
C7—C6—C5	120.5 (3)	N1B—C1B—C10B	122.2 (3)
C7—C6—H6	119.7	C1B—C2B—C3B	122.4 (4)
C5—C6—H6	119.7	C1B—C2B—H2B	118.8
C6—C7—C8	121.9 (3)	C3B—C2B—H2B	118.8
C6—C7—H7	119.0	C4B—C3B—C2B	120.2 (4)
C8—C7—H7	119.0	C4B—C3B—H3B	119.9
C9—C8—C7	119.7 (3)	C2B—C3B—H3B	119.9
C9—C8—H8	120.1	C3B—C4B—C5B	119.8 (4)
C7—C8—H8	120.1	C3B—C4B—H4B	120.1
C8—C9—N2	119.5 (3)	C5B—C4B—H4B	120.1
C8—C9—C10	119.6 (3)	C6B—C5B—C10B	119.9 (3)
N2—C9—C10	120.9 (3)	C6B—C5B—C4B	120.0 (4)
C1—C10—C9	119.7 (3)	C10B—C5B—C4B	120.1 (3)
C1—C10—C5	119.6 (3)	C7B—C6B—C5B	120.2 (4)
C9—C10—C5	120.7 (3)	C7B—C6B—H6B	119.9
N2—C11—N1	125.0 (3)	C5B—C6B—H6B	119.9
N2—C11—C12	119.6 (3)	C6B—C7B—C8B	120.8 (3)
N1—C11—C12	115.4 (2)	C6B—C7B—H7B	119.6
N4—C12—N3	127.2 (3)	C8B—C7B—H7B	119.6
N4—C12—C11	115.9 (3)	C9B—C8B—C7B	121.5 (3)
N3—C12—C11	116.9 (3)	C9B—C8B—H8B	119.2
N3—C13—C14	123.5 (3)	C7B—C8B—H8B	119.2
N3—C13—H13	118.3	C8B—C9B—N2B	119.8 (3)
C14—C13—H13	118.3	C8B—C9B—C10B	119.7 (3)
C13—C14—C15	116.7 (3)	N2B—C9B—C10B	120.4 (3)
C13—C14—H14	121.6	C5B—C10B—C1B	117.9 (3)
C15—C14—H14	121.6	C5B—C10B—C9B	117.7 (3)
N4—C15—C14	122.3 (3)	C1B—C10B—C9B	124.4 (3)
N4—C15—H15	118.8
C11—N1—C1—C2	178.4 (3)	C1A—C2A—C3A—C4A	−1.9 (5)
C11—N1—C1—C10	−1.3 (4)	C2A—C3A—C4A—C5A	1.3 (5)
N1—C1—C2—C3	179.3 (3)	C3A—C4A—C5A—C6A	−177.9 (3)
C10—C1—C2—C3	−1.1 (4)	C3A—C4A—C5A—C10A	2.9 (5)
C1—C2—C3—C4	−0.4 (5)	C4A—C5A—C6A—C7A	−178.1 (3)
C2—C3—C4—C5	1.2 (5)	C10A—C5A—C6A—C7A	1.1 (5)
C3—C4—C5—C6	179.3 (3)	C5A—C6A—C7A—C8A	2.3 (5)
C3—C4—C5—C10	−0.4 (4)	C6A—C7A—C8A—C9A	−1.6 (5)
C4—C5—C6—C7	−179.5 (3)	C7A—C8A—C9A—N2A	178.4 (3)
C10—C5—C6—C7	0.3 (4)	C7A—C8A—C9A—C10A	−2.4 (4)
C5—C6—C7—C8	0.3 (5)	C6A—C5A—C10A—C1A	174.4 (3)
C6—C7—C8—C9	−0.7 (5)	C4A—C5A—C10A—C1A	−6.4 (4)
C7—C8—C9—N2	−179.5 (3)	C6A—C5A—C10A—C9A	−4.9 (4)
C7—C8—C9—C10	0.7 (4)	C4A—C5A—C10A—C9A	174.3 (3)
C11—N2—C9—C8	178.3 (3)	C2A—C1A—C10A—C5A	5.8 (4)
C11—N2—C9—C10	−1.9 (4)	N1A—C1A—C10A—C5A	−177.6 (3)
C2—C1—C10—C9	−178.7 (3)	C2A—C1A—C10A—C9A	−175.0 (3)
N1—C1—C10—C9	1.0 (4)	N1A—C1A—C10A—C9A	1.6 (4)
C2—C1—C10—C5	1.8 (4)	C8A—C9A—C10A—C5A	5.5 (4)
N1—C1—C10—C5	−178.5 (2)	N2A—C9A—C10A—C5A	−175.3 (3)
C8—C9—C10—C1	−179.6 (3)	C8A—C9A—C10A—C1A	−173.7 (3)
N2—C9—C10—C1	0.5 (4)	N2A—C9A—C10A—C1A	5.4 (4)
C8—C9—C10—C5	−0.1 (4)	N1B—C1B—C2B—C3B	−179.6 (3)
N2—C9—C10—C5	−180.0 (2)	C10B—C1B—C2B—C3B	−0.6 (5)
C4—C5—C10—C1	−1.1 (4)	C1B—C2B—C3B—C4B	−1.3 (6)
C6—C5—C10—C1	179.2 (3)	C2B—C3B—C4B—C5B	1.4 (5)
C4—C5—C10—C9	179.4 (3)	C3B—C4B—C5B—C6B	−178.4 (3)
C6—C5—C10—C9	−0.3 (4)	C3B—C4B—C5B—C10B	0.4 (5)
C9—N2—C11—N1	1.8 (4)	C10B—C5B—C6B—C7B	−1.9 (5)
C9—N2—C11—C12	−177.6 (2)	C4B—C5B—C6B—C7B	176.9 (3)
C1—N1—C11—N2	−0.2 (4)	C5B—C6B—C7B—C8B	3.5 (5)
C1—N1—C11—C12	179.2 (2)	C6B—C7B—C8B—C9B	−0.7 (5)
C15—N4—C12—N3	−0.3 (4)	C7B—C8B—C9B—N2B	178.2 (3)
C15—N4—C12—C11	−179.3 (2)	C7B—C8B—C9B—C10B	−3.6 (5)
C13—N3—C12—N4	0.4 (4)	C6B—C5B—C10B—C1B	176.6 (3)
C13—N3—C12—C11	179.4 (2)	C4B—C5B—C10B—C1B	−2.2 (4)
N2—C11—C12—N4	177.2 (2)	C6B—C5B—C10B—C9B	−2.3 (4)
N1—C11—C12—N4	−2.2 (3)	C4B—C5B—C10B—C9B	178.9 (3)
N2—C11—C12—N3	−1.9 (4)	C2B—C1B—C10B—C5B	2.3 (4)
N1—C11—C12—N3	178.7 (2)	N1B—C1B—C10B—C5B	−178.7 (3)
C12—N3—C13—C14	−0.5 (4)	C2B—C1B—C10B—C9B	−178.9 (3)
N3—C13—C14—C15	0.5 (5)	N1B—C1B—C10B—C9B	0.1 (5)
C12—N4—C15—C14	0.2 (4)	C8B—C9B—C10B—C5B	5.0 (4)
C13—C14—C15—N4	−0.3 (4)	N2B—C9B—C10B—C5B	−176.8 (3)
N1A—C1A—C2A—C3A	−178.4 (3)	C8B—C9B—C10B—C1B	−173.8 (3)
C10A—C1A—C2A—C3A	−1.8 (5)	N2B—C9B—C10B—C1B	4.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2Ai	0.86 (3)	2.30 (3)	3.077 (4)	151 (2)
N1A—H1C···N2ii	0.87 (3)	2.42 (3)	3.153 (4)	142 (3)
N2A—H2C···N2	0.92 (3)	2.27 (3)	3.092 (4)	149 (3)
N2A—H2D···N1A	0.87 (3)	2.27 (3)	2.753 (5)	115 (2)
N1B—H1F···N2B	0.98 (4)	2.12 (3)	2.710 (5)	117 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2A i	0.86 (3)	2.30 (3)	3.077 (4)	151 (2)
N1A—H1C⋯N2ii	0.87 (3)	2.42 (3)	3.153 (4)	142 (3)
N2A—H2C⋯N2	0.92 (3)	2.27 (3)	3.092 (4)	149 (3)
N2A—H2D⋯N1A	0.87 (3)	2.27 (3)	2.753 (5)	115 (2)
N1B—H1F⋯N2B	0.98 (4)	2.12 (3)	2.710 (5)	117 (2)

Symmetry codes: (i) ; (ii) .