2,6-Diamino-pyridinium tetra-phenyl-borate-1,2-bis-(5,7-dimethyl-1,8-naphthyridin-2-yl)diazene (1/1).

In the title compound, C(5)H(8)N(3) (+)·C(24)H(20)B(-)·C(20)H(18)N(6), the 1,2-bis-(5,7-dimethyl-1,8-naphthyridin-2-yl)diazene mol-ecule is essentially planar (r.m.s. deviation = 0.0045 Å) and aligned in nearly coplanar manner with the 2,6-diamino-pyridinium ion, making a dihedral angle of 5.19 (5)°. The diamino-pyridine mol-ecule is protonated on the central pyridine N atom and the B atom bears the counter-charge. The amine groups of the diamino pyridinium cation form intra-molecular N-H⋯N hydrogen bonds, resulting in linear and bent inter-actions with the naphthyridine ring system.

Related literature

For related literature, see: Blight et al. (2009 ▶); Li et al. (2010 ▶); Raboisson et al. (2007 ▶); Roma et al. (2010 ▶); Sahoo et al. (2010 ▶).

Experimental

Crystal data

C5H8N3 +·C24H20B−·C20H18N6

M = 771.76

Triclinic,

a = 9.2700 (8) Å

b = 14.5143 (10) Å

c = 15.9754 (13) Å

α = 93.623 (5)°

β = 104.266 (5)°

γ = 101.876 (5)°

V = 2023.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.09 × 0.07 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.993, T max = 0.998

109361 measured reflections

7416 independent reflections

4071 reflections with I > 2σ(I)

R int = 0.177

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.166

S = 1.00

7416 reflections

536 parameters

H-atom parameters constrained

Δρmax = 1.28 e Å−3

Δρmin = −0.25 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) ▶; software used to prepare material for publication: SHELXTL ▶.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811012943/gw2100sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012943/gw2100Isup2.hkl

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

C5H8N3+·C24H20B−·C20H18N6	Z = 2
Mr = 771.76	F(000) = 816
Triclinic, P1	Dx = 1.266 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2700 (8) Å	Cell parameters from 4472 reflections
b = 14.5143 (10) Å	θ = 2.3–22.3°
c = 15.9754 (13) Å	µ = 0.08 mm−1
α = 93.623 (5)°	T = 150 K
β = 104.266 (5)°	Plate, red
γ = 101.876 (5)°	0.09 × 0.07 × 0.03 mm
V = 2023.8 (3) Å3

Bruker APEXII CCD diffractometer	7416 independent reflections
Radiation source: fine-focus sealed tube	4071 reflections with I > 2σ(I)
graphite	Rint = 0.177
φ and ω scans	θmax = 25.4°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.993, Tmax = 0.998	k = −17→17
109361 measured reflections	l = −19→19

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0614P)2 + 1.9563P] where P = (Fo2 + 2Fc2)/3
7416 reflections	(Δ/σ)max < 0.001
536 parameters	Δρmax = 1.28 e Å−3
0 restraints	Δρmin = −0.25 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
C1	−0.0022 (4)	0.6545 (2)	0.4229 (2)	0.0400 (9)
H1A	0.1078	0.6666	0.4506	0.060*
H1B	−0.0576	0.6544	0.4679	0.060*
H1C	−0.0232	0.7043	0.3862	0.060*
C2	−0.0538 (4)	0.5599 (2)	0.3681 (2)	0.0304 (8)
C3	−0.1584 (4)	0.4860 (2)	0.3901 (2)	0.0310 (8)
H3	−0.1940	0.4960	0.4401	0.037*
C4	−0.2084 (4)	0.4000 (2)	0.3396 (2)	0.0279 (8)
C5	−0.3193 (4)	0.3201 (2)	0.3621 (2)	0.0379 (9)
H5A	−0.3539	0.3432	0.4110	0.057*
H5B	−0.2685	0.2685	0.3784	0.057*
H5C	−0.4075	0.2967	0.3116	0.057*
C6	−0.1513 (4)	0.3876 (2)	0.2658 (2)	0.0248 (7)
C10	−0.0435 (4)	0.4647 (2)	0.2495 (2)	0.0239 (7)
C8	−0.1281 (4)	0.2975 (2)	0.1409 (2)	0.0278 (8)
H8	−0.1547	0.2411	0.1015	0.033*
C9	−0.0201 (4)	0.3773 (2)	0.1314 (2)	0.0255 (7)
C11	0.0958 (4)	0.2935 (2)	−0.0507 (2)	0.0273 (8)
C7	−0.1935 (4)	0.3032 (2)	0.2082 (2)	0.0286 (8)
H7	−0.2669	0.2506	0.2161	0.034*
C12	0.0664 (4)	0.2038 (2)	−0.0984 (2)	0.0307 (8)
H12	0.0038	0.1500	−0.0839	0.037*
C13	0.1303 (4)	0.1963 (2)	−0.1658 (2)	0.0299 (8)
H13	0.1102	0.1369	−0.2003	0.036*
C14	0.2263 (4)	0.2763 (2)	−0.1846 (2)	0.0247 (7)
C15	0.3010 (4)	0.2757 (2)	−0.2525 (2)	0.0289 (8)
C16	0.2785 (4)	0.1871 (2)	−0.3127 (2)	0.0381 (9)
H16A	0.3433	0.1997	−0.3527	0.057*
H16B	0.1710	0.1673	−0.3462	0.057*
H16C	0.3064	0.1366	−0.2786	0.057*
C17	0.3947 (4)	0.3599 (2)	−0.2600 (2)	0.0314 (8)
H17	0.4472	0.3623	−0.3042	0.038*
C18	0.4143 (4)	0.4434 (2)	−0.2028 (2)	0.0306 (8)
C19	0.5224 (4)	0.5332 (2)	−0.2113 (2)	0.0397 (9)
H19A	0.4934	0.5881	−0.1868	0.059*
H19B	0.5171	0.5377	−0.2728	0.059*
H19C	0.6270	0.5321	−0.1797	0.059*
C20	0.2503 (4)	0.3635 (2)	−0.1314 (2)	0.0258 (8)
C21	0.2972 (4)	0.6386 (2)	0.0729 (2)	0.0253 (8)
C22	0.3877 (4)	0.7207 (2)	0.0572 (2)	0.0291 (8)
H22	0.4334	0.7199	0.0102	0.035*
C23	0.4104 (4)	0.8035 (2)	0.1107 (2)	0.0311 (8)
H23	0.4703	0.8602	0.0990	0.037*
C24	0.3484 (4)	0.8065 (2)	0.1808 (2)	0.0294 (8)
H24	0.3652	0.8644	0.2168	0.035*
C25	0.2613 (4)	0.7237 (2)	0.1979 (2)	0.0264 (8)
C26	0.1943 (4)	0.2941 (2)	0.3487 (2)	0.0311 (8)
H26	0.1188	0.2950	0.2965	0.037*
C27	0.2582 (4)	0.3782 (3)	0.4048 (2)	0.0392 (9)
H27	0.2258	0.4346	0.3906	0.047*
C28	0.3695 (4)	0.3794 (3)	0.4815 (2)	0.0345 (9)
H28	0.4139	0.4363	0.5202	0.041*
C29	0.4139 (4)	0.2964 (2)	0.5004 (2)	0.0326 (8)
H29	0.4901	0.2962	0.5525	0.039*
C30	0.3483 (4)	0.2130 (2)	0.4441 (2)	0.0265 (8)
H30	0.3806	0.1569	0.4594	0.032*
C31	0.2364 (3)	0.2082 (2)	0.3658 (2)	0.0231 (7)
C32	0.2986 (4)	0.2010 (2)	0.1835 (2)	0.0270 (8)
H32	0.3137	0.2593	0.2186	0.032*
C33	0.3457 (4)	0.2021 (3)	0.1072 (2)	0.0349 (9)
H33	0.3930	0.2606	0.0915	0.042*
C34	0.3244 (4)	0.1191 (3)	0.0541 (2)	0.0349 (9)
H34	0.3558	0.1200	0.0018	0.042*
C35	0.2568 (4)	0.0346 (2)	0.0780 (2)	0.0302 (8)
H35	0.2408	−0.0232	0.0420	0.036*
C36	0.2124 (4)	0.0343 (2)	0.1546 (2)	0.0255 (7)
H36	0.1677	−0.0248	0.1703	0.031*
C37	0.2299 (3)	0.1169 (2)	0.21029 (19)	0.0212 (7)
C38	−0.1165 (3)	0.0656 (2)	0.1803 (2)	0.0228 (7)
H38	−0.0681	0.0573	0.1354	0.027*
C39	−0.2754 (4)	0.0488 (2)	0.1590 (2)	0.0251 (7)
H39	−0.3325	0.0313	0.0999	0.030*
C40	−0.3512 (4)	0.0574 (2)	0.2226 (2)	0.0265 (8)
H40	−0.4597	0.0445	0.2081	0.032*
C41	−0.2647 (4)	0.0852 (2)	0.3080 (2)	0.0263 (7)
H41	−0.3143	0.0911	0.3529	0.032*
C42	−0.1064 (4)	0.1046 (2)	0.3282 (2)	0.0250 (7)
H42	−0.0502	0.1257	0.3870	0.030*
C43	−0.0252 (3)	0.0944 (2)	0.2663 (2)	0.0217 (7)
C44	0.1203 (4)	−0.0330 (2)	0.3938 (2)	0.0255 (7)
H44	0.0220	−0.0220	0.3918	0.031*
C45	0.1699 (4)	−0.1019 (2)	0.4433 (2)	0.0311 (8)
H45	0.1057	−0.1365	0.4741	0.037*
C46	0.3121 (4)	−0.1201 (2)	0.4477 (2)	0.0294 (8)
H46	0.3461	−0.1672	0.4811	0.035*
C47	0.4040 (4)	−0.0684 (2)	0.4026 (2)	0.0270 (8)
H47	0.5025	−0.0793	0.4053	0.032*
C48	0.3519 (4)	−0.0005 (2)	0.3533 (2)	0.0236 (7)
H48	0.4165	0.0334	0.3222	0.028*
C49	0.2092 (3)	0.0205 (2)	0.34715 (19)	0.0213 (7)
B1	0.1629 (4)	0.1103 (3)	0.2967 (2)	0.0220 (8)
N1	0.0032 (3)	0.55059 (18)	0.30024 (17)	0.0270 (6)
N2	0.0221 (3)	0.45896 (18)	0.18203 (17)	0.0258 (6)
N3	0.0568 (3)	0.37649 (19)	0.06346 (17)	0.0267 (6)
N4	0.0220 (3)	0.2969 (2)	0.01827 (18)	0.0293 (7)
N5	0.1833 (3)	0.37119 (18)	−0.06553 (17)	0.0281 (7)
N6	0.3438 (3)	0.44677 (18)	−0.14110 (18)	0.0289 (7)
N7	0.2625 (3)	0.55485 (19)	0.02383 (17)	0.0307 (7)
H7A	0.2029	0.5055	0.0369	0.037*
H7B	0.2993	0.5491	−0.0215	0.037*
N8	0.2360 (3)	0.64251 (18)	0.14261 (16)	0.0253 (6)
H8A	0.1778	0.5904	0.1523	0.030*
N9	0.1999 (4)	0.7172 (2)	0.26545 (18)	0.0381 (8)
H9A	0.1460	0.6624	0.2729	0.046*
H9B	0.2135	0.7677	0.3025	0.046*

	U11	U22	U33	U12	U13	U23
C1	0.051 (2)	0.031 (2)	0.040 (2)	0.0054 (18)	0.0177 (19)	0.0012 (17)
C2	0.0304 (19)	0.028 (2)	0.0332 (19)	0.0081 (16)	0.0083 (16)	0.0038 (16)
C3	0.031 (2)	0.032 (2)	0.0320 (19)	0.0080 (16)	0.0111 (16)	0.0055 (16)
C4	0.0272 (18)	0.027 (2)	0.0334 (19)	0.0086 (15)	0.0111 (15)	0.0101 (16)
C5	0.039 (2)	0.035 (2)	0.043 (2)	0.0053 (17)	0.0182 (18)	0.0080 (17)
C6	0.0225 (17)	0.0244 (19)	0.0273 (18)	0.0067 (14)	0.0036 (14)	0.0086 (15)
C10	0.0247 (17)	0.0219 (18)	0.0259 (17)	0.0074 (15)	0.0056 (15)	0.0061 (14)
C8	0.0320 (19)	0.0220 (19)	0.0246 (17)	0.0021 (15)	0.0021 (15)	0.0035 (14)
C9	0.0271 (18)	0.0265 (19)	0.0232 (17)	0.0086 (15)	0.0045 (14)	0.0057 (15)
C11	0.0248 (18)	0.026 (2)	0.0300 (18)	0.0049 (15)	0.0064 (15)	0.0014 (15)
C7	0.0282 (19)	0.0254 (19)	0.0305 (19)	0.0032 (15)	0.0059 (15)	0.0085 (15)
C12	0.0295 (19)	0.024 (2)	0.034 (2)	0.0011 (15)	0.0064 (16)	−0.0005 (15)
C13	0.0312 (19)	0.0227 (19)	0.0333 (19)	0.0046 (15)	0.0068 (16)	−0.0028 (15)
C14	0.0248 (18)	0.0250 (19)	0.0248 (17)	0.0086 (15)	0.0050 (14)	0.0034 (14)
C15	0.0292 (19)	0.030 (2)	0.0285 (18)	0.0141 (16)	0.0028 (15)	0.0055 (15)
C16	0.045 (2)	0.036 (2)	0.036 (2)	0.0103 (18)	0.0164 (18)	−0.0015 (17)
C17	0.031 (2)	0.034 (2)	0.0330 (19)	0.0117 (17)	0.0116 (16)	0.0074 (16)
C18	0.0258 (19)	0.030 (2)	0.035 (2)	0.0059 (15)	0.0059 (16)	0.0086 (16)
C19	0.039 (2)	0.032 (2)	0.049 (2)	0.0049 (18)	0.0147 (19)	0.0100 (18)
C20	0.0251 (18)	0.0220 (19)	0.0285 (18)	0.0064 (15)	0.0030 (15)	0.0020 (15)
C21	0.0256 (18)	0.0241 (19)	0.0252 (17)	0.0076 (15)	0.0035 (15)	0.0031 (15)
C22	0.0315 (19)	0.0240 (19)	0.0314 (19)	0.0030 (15)	0.0105 (16)	0.0012 (15)
C23	0.031 (2)	0.025 (2)	0.036 (2)	−0.0006 (15)	0.0103 (16)	0.0052 (16)
C24	0.0317 (19)	0.0196 (18)	0.0343 (19)	0.0021 (15)	0.0080 (16)	−0.0004 (15)
C25	0.0277 (18)	0.0224 (19)	0.0274 (18)	0.0046 (15)	0.0054 (15)	0.0017 (15)
C26	0.0285 (19)	0.032 (2)	0.0317 (19)	0.0089 (16)	0.0040 (15)	0.0028 (16)
C27	0.050 (2)	0.026 (2)	0.042 (2)	0.0108 (18)	0.0122 (19)	0.0004 (17)
C28	0.037 (2)	0.030 (2)	0.033 (2)	0.0001 (17)	0.0120 (17)	−0.0062 (16)
C29	0.0281 (19)	0.038 (2)	0.0261 (18)	0.0005 (16)	0.0054 (15)	−0.0028 (16)
C30	0.0263 (18)	0.0284 (19)	0.0260 (17)	0.0051 (15)	0.0106 (15)	0.0016 (15)
C31	0.0197 (17)	0.0272 (19)	0.0248 (17)	0.0049 (14)	0.0104 (14)	0.0041 (14)
C32	0.0280 (18)	0.0259 (19)	0.0285 (18)	0.0053 (15)	0.0115 (15)	0.0013 (15)
C33	0.040 (2)	0.035 (2)	0.033 (2)	0.0036 (17)	0.0178 (17)	0.0129 (17)
C34	0.036 (2)	0.048 (2)	0.0246 (18)	0.0108 (18)	0.0145 (16)	0.0063 (17)
C35	0.0314 (19)	0.035 (2)	0.0245 (18)	0.0095 (16)	0.0083 (15)	−0.0037 (15)
C36	0.0217 (17)	0.0265 (19)	0.0279 (18)	0.0045 (14)	0.0065 (14)	0.0037 (15)
C37	0.0134 (15)	0.0256 (18)	0.0229 (16)	0.0043 (13)	0.0020 (13)	0.0019 (14)
C38	0.0231 (17)	0.0207 (18)	0.0264 (17)	0.0055 (14)	0.0095 (14)	0.0031 (14)
C39	0.0212 (17)	0.0252 (19)	0.0257 (17)	0.0026 (14)	0.0025 (14)	0.0036 (14)
C40	0.0158 (16)	0.0262 (19)	0.0359 (19)	0.0026 (14)	0.0064 (15)	0.0029 (15)
C41	0.0235 (18)	0.0271 (19)	0.0332 (19)	0.0076 (15)	0.0145 (15)	0.0063 (15)
C42	0.0237 (18)	0.0278 (19)	0.0226 (17)	0.0057 (15)	0.0050 (14)	0.0013 (14)
C43	0.0208 (17)	0.0197 (17)	0.0248 (17)	0.0035 (14)	0.0071 (14)	0.0029 (13)
C44	0.0200 (17)	0.0273 (19)	0.0292 (18)	0.0027 (14)	0.0094 (14)	0.0019 (15)
C45	0.036 (2)	0.028 (2)	0.0286 (18)	0.0024 (16)	0.0104 (16)	0.0057 (15)
C46	0.035 (2)	0.0248 (19)	0.0266 (18)	0.0090 (16)	0.0036 (15)	0.0044 (15)
C47	0.0244 (18)	0.0285 (19)	0.0282 (18)	0.0095 (15)	0.0059 (15)	−0.0016 (15)
C48	0.0222 (17)	0.0242 (18)	0.0242 (17)	0.0030 (14)	0.0080 (14)	0.0014 (14)
C49	0.0196 (16)	0.0222 (18)	0.0191 (16)	0.0009 (14)	0.0047 (13)	−0.0037 (13)
B1	0.0169 (18)	0.026 (2)	0.0214 (18)	0.0031 (16)	0.0046 (15)	0.0003 (16)
N1	0.0303 (16)	0.0236 (16)	0.0263 (15)	0.0054 (13)	0.0069 (13)	0.0020 (12)
N2	0.0262 (15)	0.0218 (16)	0.0281 (15)	0.0050 (12)	0.0050 (12)	0.0039 (12)
N3	0.0276 (16)	0.0246 (16)	0.0255 (15)	0.0053 (13)	0.0040 (12)	0.0004 (13)
N4	0.0297 (16)	0.0255 (16)	0.0308 (16)	0.0053 (13)	0.0056 (13)	0.0016 (13)
N5	0.0281 (16)	0.0216 (16)	0.0314 (16)	0.0016 (13)	0.0058 (13)	0.0011 (12)
N6	0.0274 (16)	0.0229 (16)	0.0357 (16)	0.0048 (13)	0.0080 (13)	0.0033 (13)
N7	0.0386 (17)	0.0246 (16)	0.0268 (15)	0.0026 (13)	0.0101 (13)	−0.0020 (13)
N8	0.0268 (15)	0.0198 (15)	0.0280 (15)	0.0018 (12)	0.0080 (12)	0.0028 (12)
N9	0.054 (2)	0.0242 (16)	0.0350 (17)	−0.0028 (14)	0.0217 (15)	−0.0037 (13)

C1—C2	1.501 (5)	C25—N8	1.370 (4)
C1—H1A	0.9800	C26—C27	1.395 (5)
C1—H1B	0.9800	C26—C31	1.405 (4)
C1—H1C	0.9800	C26—H26	0.9500
C2—N1	1.328 (4)	C27—C28	1.390 (5)
C2—C3	1.416 (5)	C27—H27	0.9500
C3—C4	1.369 (5)	C28—C29	1.379 (5)
C3—H3	0.9500	C28—H28	0.9500
C4—C6	1.422 (4)	C29—C30	1.392 (4)
C4—C5	1.508 (5)	C29—H29	0.9500
C5—H5A	0.9800	C30—C31	1.402 (4)
C5—H5B	0.9800	C30—H30	0.9500
C5—H5C	0.9800	C31—B1	1.653 (5)
C6—C7	1.409 (4)	C32—C33	1.393 (4)
C6—C10	1.422 (4)	C32—C37	1.399 (4)
C10—N2	1.368 (4)	C32—H32	0.9500
C10—N1	1.370 (4)	C33—C34	1.379 (5)
C8—C7	1.363 (5)	C33—H33	0.9500
C8—C9	1.410 (4)	C34—C35	1.379 (5)
C8—H8	0.9500	C34—H34	0.9500
C9—N2	1.321 (4)	C35—C36	1.385 (4)
C9—N3	1.439 (4)	C35—H35	0.9500
C11—N5	1.317 (4)	C36—C37	1.403 (4)
C11—C12	1.406 (4)	C36—H36	0.9500
C11—N4	1.437 (4)	C37—B1	1.648 (5)
C7—H7	0.9500	C38—C39	1.393 (4)
C12—C13	1.361 (5)	C38—C43	1.409 (4)
C12—H12	0.9500	C38—H38	0.9500
C13—C14	1.407 (5)	C39—C40	1.382 (4)
C13—H13	0.9500	C39—H39	0.9500
C14—C15	1.424 (5)	C40—C41	1.388 (4)
C14—C20	1.424 (4)	C40—H40	0.9500
C15—C17	1.377 (5)	C41—C42	1.387 (4)
C15—C16	1.503 (5)	C41—H41	0.9500
C16—H16A	0.9800	C42—C43	1.401 (4)
C16—H16B	0.9800	C42—H42	0.9500
C16—H16C	0.9800	C43—B1	1.653 (4)
C17—C18	1.423 (5)	C44—C45	1.395 (4)
C17—H17	0.9500	C44—C49	1.396 (4)
C18—N6	1.313 (4)	C44—H44	0.9500
C18—C19	1.507 (5)	C45—C46	1.383 (5)
C19—H19A	0.9800	C45—H45	0.9500
C19—H19B	0.9800	C46—C47	1.384 (5)
C19—H19C	0.9800	C46—H46	0.9500
C20—N5	1.357 (4)	C47—C48	1.389 (4)
C20—N6	1.377 (4)	C47—H47	0.9500
C21—N7	1.337 (4)	C48—C49	1.400 (4)
C21—N8	1.372 (4)	C48—H48	0.9500
C21—C22	1.385 (4)	C49—B1	1.650 (5)
C22—C23	1.377 (4)	N3—N4	1.259 (3)
C22—H22	0.9500	N7—H7A	0.8800
C23—C24	1.382 (5)	N7—H7B	0.8800
C23—H23	0.9500	N8—H8A	0.8800
C24—C25	1.386 (4)	N9—H9A	0.8800
C24—H24	0.9500	N9—H9B	0.8800
C25—N9	1.338 (4)
C2—C1—H1A	109.5	C28—C27—C26	120.0 (3)
C2—C1—H1B	109.5	C28—C27—H27	120.0
H1A—C1—H1B	109.5	C26—C27—H27	120.0
C2—C1—H1C	109.5	C29—C28—C27	118.7 (3)
H1A—C1—H1C	109.5	C29—C28—H28	120.7
H1B—C1—H1C	109.5	C27—C28—H28	120.7
N1—C2—C3	123.3 (3)	C28—C29—C30	120.7 (3)
N1—C2—C1	117.0 (3)	C28—C29—H29	119.6
C3—C2—C1	119.7 (3)	C30—C29—H29	119.6
C4—C3—C2	120.2 (3)	C29—C30—C31	122.8 (3)
C4—C3—H3	119.9	C29—C30—H30	118.6
C2—C3—H3	119.9	C31—C30—H30	118.6
C3—C4—C6	118.1 (3)	C30—C31—C26	114.8 (3)
C3—C4—C5	121.0 (3)	C30—C31—B1	123.1 (3)
C6—C4—C5	120.9 (3)	C26—C31—B1	122.1 (3)
C4—C5—H5A	109.5	C33—C32—C37	122.3 (3)
C4—C5—H5B	109.5	C33—C32—H32	118.9
H5A—C5—H5B	109.5	C37—C32—H32	118.9
C4—C5—H5C	109.5	C34—C33—C32	120.5 (3)
H5A—C5—H5C	109.5	C34—C33—H33	119.7
H5B—C5—H5C	109.5	C32—C33—H33	119.7
C7—C6—C4	124.0 (3)	C33—C34—C35	119.1 (3)
C7—C6—C10	117.8 (3)	C33—C34—H34	120.4
C4—C6—C10	118.2 (3)	C35—C34—H34	120.4
N2—C10—N1	114.6 (3)	C34—C35—C36	119.8 (3)
N2—C10—C6	122.7 (3)	C34—C35—H35	120.1
N1—C10—C6	122.7 (3)	C36—C35—H35	120.1
C7—C8—C9	118.3 (3)	C35—C36—C37	123.3 (3)
C7—C8—H8	120.8	C35—C36—H36	118.3
C9—C8—H8	120.8	C37—C36—H36	118.3
N2—C9—C8	125.1 (3)	C32—C37—C36	115.0 (3)
N2—C9—N3	113.0 (3)	C32—C37—B1	125.1 (3)
C8—C9—N3	121.9 (3)	C36—C37—B1	119.8 (3)
N5—C11—C12	124.9 (3)	C39—C38—C43	122.3 (3)
N5—C11—N4	120.0 (3)	C39—C38—H38	118.9
C12—C11—N4	115.1 (3)	C43—C38—H38	118.9
C8—C7—C6	119.5 (3)	C40—C39—C38	120.9 (3)
C8—C7—H7	120.3	C40—C39—H39	119.6
C6—C7—H7	120.3	C38—C39—H39	119.6
C13—C12—C11	118.0 (3)	C39—C40—C41	118.4 (3)
C13—C12—H12	121.0	C39—C40—H40	120.8
C11—C12—H12	121.0	C41—C40—H40	120.8
C12—C13—C14	120.1 (3)	C42—C41—C40	120.3 (3)
C12—C13—H13	120.0	C42—C41—H41	119.8
C14—C13—H13	120.0	C40—C41—H41	119.8
C13—C14—C15	124.5 (3)	C41—C42—C43	123.2 (3)
C13—C14—C20	117.3 (3)	C41—C42—H42	118.4
C15—C14—C20	118.1 (3)	C43—C42—H42	118.4
C17—C15—C14	116.9 (3)	C42—C43—C38	114.9 (3)
C17—C15—C16	121.8 (3)	C42—C43—B1	120.3 (3)
C14—C15—C16	121.3 (3)	C38—C43—B1	124.7 (3)
C15—C16—H16A	109.5	C45—C44—C49	122.7 (3)
C15—C16—H16B	109.5	C45—C44—H44	118.6
H16A—C16—H16B	109.5	C49—C44—H44	118.6
C15—C16—H16C	109.5	C46—C45—C44	120.4 (3)
H16A—C16—H16C	109.5	C46—C45—H45	119.8
H16B—C16—H16C	109.5	C44—C45—H45	119.8
C15—C17—C18	121.2 (3)	C45—C46—C47	118.7 (3)
C15—C17—H17	119.4	C45—C46—H46	120.6
C18—C17—H17	119.4	C47—C46—H46	120.6
N6—C18—C17	123.3 (3)	C46—C47—C48	120.0 (3)
N6—C18—C19	117.2 (3)	C46—C47—H47	120.0
C17—C18—C19	119.4 (3)	C48—C47—H47	120.0
C18—C19—H19A	109.5	C47—C48—C49	123.3 (3)
C18—C19—H19B	109.5	C47—C48—H48	118.3
H19A—C19—H19B	109.5	C49—C48—H48	118.3
C18—C19—H19C	109.5	C44—C49—C48	114.9 (3)
H19A—C19—H19C	109.5	C44—C49—B1	124.1 (3)
H19B—C19—H19C	109.5	C48—C49—B1	120.6 (3)
N5—C20—N6	114.0 (3)	C37—B1—C49	109.5 (3)
N5—C20—C14	122.4 (3)	C37—B1—C31	111.1 (3)
N6—C20—C14	123.6 (3)	C49—B1—C31	108.1 (2)
N7—C21—N8	116.9 (3)	C37—B1—C43	109.4 (2)
N7—C21—C22	124.6 (3)	C49—B1—C43	109.6 (3)
N8—C21—C22	118.5 (3)	C31—B1—C43	109.2 (3)
C23—C22—C21	119.1 (3)	C2—N1—C10	117.5 (3)
C23—C22—H22	120.5	C9—N2—C10	116.5 (3)
C21—C22—H22	120.5	N4—N3—C9	112.6 (3)
C22—C23—C24	121.9 (3)	N3—N4—C11	114.2 (3)
C22—C23—H23	119.1	C11—N5—C20	117.3 (3)
C24—C23—H23	119.1	C18—N6—C20	116.9 (3)
C23—C24—C25	119.0 (3)	C21—N7—H7A	120.0
C23—C24—H24	120.5	C21—N7—H7B	120.0
C25—C24—H24	120.5	H7A—N7—H7B	120.0
N9—C25—N8	117.2 (3)	C25—N8—C21	123.1 (3)
N9—C25—C24	124.4 (3)	C25—N8—H8A	118.5
N8—C25—C24	118.4 (3)	C21—N8—H8A	118.5
C27—C26—C31	123.0 (3)	C25—N9—H9A	120.0
C27—C26—H26	118.5	C25—N9—H9B	120.0
C31—C26—H26	118.5	H9A—N9—H9B	120.0
N1—C2—C3—C4	−1.3 (5)	C41—C42—C43—B1	−175.0 (3)
C1—C2—C3—C4	178.8 (3)	C39—C38—C43—C42	0.2 (4)
C2—C3—C4—C6	0.5 (5)	C39—C38—C43—B1	176.8 (3)
C2—C3—C4—C5	179.8 (3)	C49—C44—C45—C46	−0.2 (5)
C3—C4—C6—C7	−179.7 (3)	C44—C45—C46—C47	0.3 (5)
C5—C4—C6—C7	1.0 (5)	C45—C46—C47—C48	−0.7 (5)
C3—C4—C6—C10	1.1 (4)	C46—C47—C48—C49	1.0 (5)
C5—C4—C6—C10	−178.1 (3)	C45—C44—C49—C48	0.3 (4)
C7—C6—C10—N2	−1.5 (5)	C45—C44—C49—B1	−173.1 (3)
C4—C6—C10—N2	177.7 (3)	C47—C48—C49—C44	−0.7 (4)
C7—C6—C10—N1	178.6 (3)	C47—C48—C49—B1	172.9 (3)
C4—C6—C10—N1	−2.1 (5)	C32—C37—B1—C49	−138.5 (3)
C7—C8—C9—N2	−1.2 (5)	C36—C37—B1—C49	45.1 (4)
C7—C8—C9—N3	178.6 (3)	C32—C37—B1—C31	−19.2 (4)
C9—C8—C7—C6	−0.2 (5)	C36—C37—B1—C31	164.3 (3)
C4—C6—C7—C8	−177.7 (3)	C32—C37—B1—C43	101.4 (3)
C10—C6—C7—C8	1.4 (5)	C36—C37—B1—C43	−75.1 (3)
N5—C11—C12—C13	−1.2 (5)	C44—C49—B1—C37	−148.7 (3)
N4—C11—C12—C13	178.6 (3)	C48—C49—B1—C37	38.2 (4)
C11—C12—C13—C14	1.8 (5)	C44—C49—B1—C31	90.2 (3)
C12—C13—C14—C15	178.8 (3)	C48—C49—B1—C31	−82.9 (3)
C12—C13—C14—C20	−0.9 (5)	C44—C49—B1—C43	−28.7 (4)
C13—C14—C15—C17	−178.0 (3)	C48—C49—B1—C43	158.2 (3)
C20—C14—C15—C17	1.7 (4)	C30—C31—B1—C37	−105.9 (3)
C13—C14—C15—C16	1.8 (5)	C26—C31—B1—C37	72.1 (4)
C20—C14—C15—C16	−178.5 (3)	C30—C31—B1—C49	14.3 (4)
C14—C15—C17—C18	−0.5 (5)	C26—C31—B1—C49	−167.8 (3)
C16—C15—C17—C18	179.7 (3)	C30—C31—B1—C43	133.4 (3)
C15—C17—C18—N6	−1.3 (5)	C26—C31—B1—C43	−48.6 (4)
C15—C17—C18—C19	177.8 (3)	C42—C43—B1—C37	−167.8 (3)
C13—C14—C20—N5	−0.7 (5)	C38—C43—B1—C37	15.7 (4)
C15—C14—C20—N5	179.5 (3)	C42—C43—B1—C49	72.1 (4)
C13—C14—C20—N6	178.5 (3)	C38—C43—B1—C49	−104.4 (3)
C15—C14—C20—N6	−1.2 (5)	C42—C43—B1—C31	−46.1 (4)
N7—C21—C22—C23	177.5 (3)	C38—C43—B1—C31	137.4 (3)
N8—C21—C22—C23	−1.3 (5)	C3—C2—N1—C10	0.4 (5)
C21—C22—C23—C24	1.6 (5)	C1—C2—N1—C10	−179.8 (3)
C22—C23—C24—C25	0.2 (5)	N2—C10—N1—C2	−178.5 (3)
C23—C24—C25—N9	177.6 (3)	C6—C10—N1—C2	1.4 (4)
C23—C24—C25—N8	−2.1 (5)	C8—C9—N2—C10	1.2 (5)
C31—C26—C27—C28	0.3 (5)	N3—C9—N2—C10	−178.6 (3)
C26—C27—C28—C29	−0.1 (5)	N1—C10—N2—C9	−179.9 (3)
C27—C28—C29—C30	−0.3 (5)	C6—C10—N2—C9	0.2 (4)
C28—C29—C30—C31	0.7 (5)	N2—C9—N3—N4	176.5 (3)
C29—C30—C31—C26	−0.5 (5)	C8—C9—N3—N4	−3.2 (4)
C29—C30—C31—B1	177.5 (3)	C9—N3—N4—C11	179.6 (3)
C27—C26—C31—C30	0.1 (5)	N5—C11—N4—N3	−4.2 (4)
C27—C26—C31—B1	−178.0 (3)	C12—C11—N4—N3	176.0 (3)
C37—C32—C33—C34	0.7 (5)	C12—C11—N5—C20	−0.4 (5)
C32—C33—C34—C35	−0.5 (5)	N4—C11—N5—C20	179.8 (3)
C33—C34—C35—C36	−0.3 (5)	N6—C20—N5—C11	−178.0 (3)
C34—C35—C36—C37	1.1 (5)	C14—C20—N5—C11	1.4 (5)
C33—C32—C37—C36	0.1 (5)	C17—C18—N6—C20	1.8 (5)
C33—C32—C37—B1	−176.5 (3)	C19—C18—N6—C20	−177.3 (3)
C35—C36—C37—C32	−0.9 (5)	N5—C20—N6—C18	178.8 (3)
C35—C36—C37—B1	175.9 (3)	C14—C20—N6—C18	−0.6 (5)
C43—C38—C39—C40	−1.9 (5)	N9—C25—N8—C21	−177.4 (3)
C38—C39—C40—C41	1.5 (5)	C24—C25—N8—C21	2.3 (5)
C39—C40—C41—C42	0.5 (5)	N7—C21—N8—C25	−179.5 (3)
C40—C41—C42—C43	−2.3 (5)	C22—C21—N8—C25	−0.6 (5)
C41—C42—C43—C38	1.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7A···N3	0.88	2.21	3.084 (9)	177
N7—H7B···N6	0.88	2.51	3.304 (12)	150
N8—H8A···N2	0.88	2.30	3.175 (9)	177
N9—H9A···N1	0.88	2.02	2.887 (11)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7A⋯N3	0.88	2.21	3.084 (9)	177
N7—H7B⋯N6	0.88	2.51	3.304 (12)	150
N8—H8A⋯N2	0.88	2.30	3.175 (9)	177
N9—H9A⋯N1	0.88	2.02	2.887 (11)	170