N,N,N',N',N''-Penta-methyl-N''-[3-(tri-methyl-aza-nium-yl)prop-yl]guanidinium bis-(tetra-phenyl-borate).

In the crystal structure of the title salt, C(12)H(30)N(4) (2+)·2C(24)H(20)B(-), the C-N bond lengths in the central CN(3) unit of the guanidinium ion are 1.3388 (17), 1.3390 (16) and 1.3540 (17) Å, indicating partial double-bond character in each. The central C atom is bonded to the three N atoms in a nearly ideal trigonal-planar geometry and the positive charge is delocalized in the CN(3) plane. The bonds between the N atoms and the terminal C-methyl groups of the guanidinium moiety, all have values close to a typical single bond [1.4630 (16)-1.4697 (17) Å]. C-H⋯π inter-actions are present between the guanidinium H atoms and the phenyl C atoms of one tetra-phenyl-borate ion. The phenyl rings form a kind of aromatic pocket, in which the guanidinium ion is embedded.

Related literature

For the synthesis of N′′-[3-(dimethyl­amino)­prop­yl]- N,N,N′,N′-tetra­methyl­guanidine, see: Tiritiris & Kantlehner (2012 ▶). For the crystal structures of alkali metal tetra­phenyl­borates, see: Behrens et al. (2012 ▶).

Experimental

Crystal data

C12H30N4 +·2C24H20B−

M = 868.82

Monoclinic,

a = 17.7622 (4) Å

b = 16.1667 (3) Å

c = 17.3787 (4) Å

β = 98.045 (1)°

V = 4941.29 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.27 × 0.25 × 0.20 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

22713 measured reflections

12056 independent reflections

8821 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.108

S = 1.02

12056 reflections

603 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.27 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813001992/zl2530sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001992/zl2530Isup2.hkl

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

C12H30N4+·2C24H20B−	F(000) = 1872
Mr = 868.82	Dx = 1.168 Mg m−3
Monoclinic, P21/c	Melting point: 502 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 17.7622 (4) Å	Cell parameters from 11929 reflections
b = 16.1667 (3) Å	θ = 0.4–28.3°
c = 17.3787 (4) Å	µ = 0.07 mm−1
β = 98.045 (1)°	T = 100 K
V = 4941.29 (18) Å3	Polyhedral, colorless
Z = 4	0.27 × 0.25 × 0.20 mm

Bruker–Nonius KappaCCD diffractometer	8821 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.038
Graphite monochromator	θmax = 28.3°, θmin = 1.2°
φ scans, and ω scans	h = −23→23
22713 measured reflections	k = −21→21
12056 independent reflections	l = −23→23

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.108	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0389P)2 + 2.0808P] where P = (Fo2 + 2Fc2)/3
12056 reflections	(Δ/σ)max < 0.001
603 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.27 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	0.72188 (6)	0.33127 (7)	0.03324 (6)	0.0155 (2)
N2	0.82034 (6)	0.28130 (7)	0.12425 (6)	0.0163 (2)
N3	0.81518 (6)	0.42077 (7)	0.09366 (6)	0.0152 (2)
N4	0.73663 (6)	0.66166 (7)	0.24912 (6)	0.0134 (2)
C1	0.78526 (7)	0.34387 (8)	0.08336 (7)	0.0136 (2)
C2	0.70205 (8)	0.38292 (9)	−0.03593 (8)	0.0205 (3)
H2A	0.6572	0.4163	−0.0300	0.031*
H2B	0.6909	0.3475	−0.0819	0.031*
H2C	0.7448	0.4195	−0.0422	0.031*
C3	0.66849 (8)	0.26374 (9)	0.04174 (9)	0.0216 (3)
H3A	0.6774	0.2183	0.0068	0.032*
H3B	0.6162	0.2839	0.0285	0.032*
H3C	0.6762	0.2439	0.0956	0.032*
C4	0.82067 (8)	0.19610 (9)	0.09563 (9)	0.0211 (3)
H4A	0.7872	0.1620	0.1229	0.032*
H4B	0.8725	0.1741	0.1051	0.032*
H4C	0.8025	0.1952	0.0397	0.032*
C5	0.86344 (8)	0.29427 (10)	0.20146 (8)	0.0231 (3)
H5A	0.9179	0.2887	0.1986	0.035*
H5B	0.8482	0.2530	0.2376	0.035*
H5C	0.8531	0.3498	0.2199	0.035*
C6	0.89702 (7)	0.43361 (9)	0.09621 (9)	0.0208 (3)
H6A	0.9211	0.3816	0.0838	0.031*
H6B	0.9188	0.4518	0.1484	0.031*
H6C	0.9060	0.4759	0.0582	0.031*
C7	0.76724 (7)	0.49447 (8)	0.09672 (7)	0.0156 (3)
H7A	0.7133	0.4773	0.0920	0.019*
H7B	0.7731	0.5309	0.0521	0.019*
C8	0.78810 (7)	0.54320 (8)	0.17278 (7)	0.0153 (3)
H8A	0.7989	0.5045	0.2171	0.018*
H8B	0.8341	0.5771	0.1700	0.018*
C9	0.72114 (7)	0.59887 (8)	0.18394 (7)	0.0146 (2)
H9A	0.7050	0.6289	0.1348	0.017*
H9B	0.6781	0.5635	0.1942	0.017*
C10	0.78839 (8)	0.72864 (8)	0.22812 (8)	0.0183 (3)
H10A	0.7986	0.7678	0.2714	0.027*
H10B	0.7641	0.7578	0.1817	0.027*
H10C	0.8364	0.7042	0.2175	0.027*
C11	0.66238 (7)	0.70012 (9)	0.26196 (8)	0.0183 (3)
H11A	0.6719	0.7443	0.3008	0.027*
H11B	0.6297	0.6579	0.2806	0.027*
H11C	0.6371	0.7233	0.2129	0.027*
C12	0.77035 (8)	0.62061 (9)	0.32345 (7)	0.0176 (3)
H12A	0.8213	0.6001	0.3183	0.026*
H12B	0.7380	0.5742	0.3346	0.026*
H12C	0.7738	0.6607	0.3661	0.026*
B1	0.92120 (8)	0.77122 (9)	0.01258 (8)	0.0130 (3)
C13	0.84884 (7)	0.70967 (8)	−0.01978 (7)	0.0139 (2)
C14	0.85773 (8)	0.64051 (9)	−0.06727 (8)	0.0197 (3)
H14A	0.9076	0.6256	−0.0759	0.024*
C15	0.79684 (9)	0.59327 (9)	−0.10199 (8)	0.0230 (3)
H15A	0.8058	0.5482	−0.1347	0.028*
C16	0.72308 (9)	0.61134 (9)	−0.08931 (8)	0.0222 (3)
H16A	0.6812	0.5800	−0.1138	0.027*
C17	0.71217 (8)	0.67606 (9)	−0.04010 (8)	0.0211 (3)
H17A	0.6624	0.6884	−0.0292	0.025*
C18	0.77377 (8)	0.72337 (9)	−0.00630 (8)	0.0172 (3)
H18A	0.7644	0.7671	0.0276	0.021*
C19	0.90010 (7)	0.83216 (8)	0.08230 (7)	0.0131 (2)
C20	0.84233 (7)	0.89228 (8)	0.06892 (7)	0.0148 (2)
H20A	0.8138	0.8959	0.0186	0.018*
C21	0.82520 (7)	0.94659 (8)	0.12597 (8)	0.0170 (3)
H21A	0.7862	0.9867	0.1139	0.020*
C22	0.86491 (8)	0.94244 (9)	0.20072 (8)	0.0180 (3)
H22A	0.8529	0.9788	0.2402	0.022*
C23	0.92215 (8)	0.88448 (9)	0.21657 (8)	0.0179 (3)
H23A	0.9499	0.8810	0.2673	0.021*
C24	0.93943 (7)	0.83101 (8)	0.15836 (7)	0.0157 (3)
H24A	0.9795	0.7922	0.1707	0.019*
C25	0.99644 (7)	0.71673 (8)	0.04716 (7)	0.0144 (2)
C26	0.99181 (8)	0.63813 (9)	0.08039 (8)	0.0189 (3)
H26A	0.9434	0.6125	0.0778	0.023*
C27	1.05539 (8)	0.59606 (9)	0.11711 (8)	0.0212 (3)
H27A	1.0499	0.5426	0.1383	0.025*
C28	1.12671 (8)	0.63228 (9)	0.12264 (8)	0.0201 (3)
H28A	1.1702	0.6042	0.1480	0.024*
C29	1.13376 (8)	0.71018 (9)	0.09060 (8)	0.0186 (3)
H29A	1.1823	0.7357	0.0941	0.022*
C30	1.06967 (7)	0.75080 (8)	0.05334 (8)	0.0163 (3)
H30A	1.0758	0.8037	0.0312	0.020*
C31	0.94239 (7)	0.82836 (8)	−0.06068 (7)	0.0135 (2)
C32	0.95366 (7)	0.79298 (8)	−0.13195 (8)	0.0159 (3)
H32A	0.9483	0.7348	−0.1381	0.019*
C33	0.97242 (7)	0.83945 (9)	−0.19412 (7)	0.0170 (3)
H33A	0.9794	0.8126	−0.2413	0.020*
C34	0.98100 (7)	0.92435 (9)	−0.18763 (8)	0.0179 (3)
H34A	0.9929	0.9564	−0.2302	0.022*
C35	0.97190 (8)	0.96169 (9)	−0.11763 (8)	0.0189 (3)
H35A	0.9786	1.0197	−0.1117	0.023*
C36	0.95301 (7)	0.91444 (8)	−0.05604 (7)	0.0161 (3)
H36A	0.9470	0.9416	−0.0088	0.019*
B2	0.56950 (8)	0.36867 (9)	0.27014 (8)	0.0139 (3)
C37	0.49422 (7)	0.35924 (8)	0.31507 (8)	0.0165 (3)
C38	0.49765 (8)	0.31050 (9)	0.38226 (8)	0.0215 (3)
H38A	0.5429	0.2803	0.3990	0.026*
C39	0.43758 (9)	0.30464 (10)	0.42539 (9)	0.0284 (3)
H39A	0.4426	0.2718	0.4711	0.034*
C40	0.37027 (9)	0.34683 (10)	0.40166 (10)	0.0325 (4)
H40A	0.3297	0.3449	0.4319	0.039*
C41	0.36309 (9)	0.39164 (10)	0.33346 (11)	0.0300 (4)
H41A	0.3165	0.4188	0.3154	0.036*
C42	0.42396 (8)	0.39720 (9)	0.29082 (9)	0.0213 (3)
H42A	0.4175	0.4278	0.2437	0.026*
C43	0.55692 (7)	0.44382 (8)	0.20609 (7)	0.0147 (3)
C44	0.53044 (7)	0.52126 (8)	0.22770 (8)	0.0168 (3)
H44A	0.5221	0.5290	0.2800	0.020*
C45	0.51585 (7)	0.58709 (9)	0.17622 (8)	0.0188 (3)
H45A	0.4956	0.6374	0.1929	0.023*
C46	0.53105 (8)	0.57886 (9)	0.10041 (8)	0.0194 (3)
H46A	0.5213	0.6233	0.0646	0.023*
C47	0.56067 (7)	0.50486 (9)	0.07758 (8)	0.0185 (3)
H47A	0.5731	0.4993	0.0264	0.022*
C48	0.57231 (7)	0.43850 (9)	0.12931 (7)	0.0159 (3)
H48A	0.5913	0.3880	0.1118	0.019*
C49	0.58100 (7)	0.27853 (8)	0.22960 (7)	0.0149 (3)
C50	0.52557 (8)	0.25007 (9)	0.16949 (8)	0.0182 (3)
H50A	0.4836	0.2849	0.1520	0.022*
C51	0.52972 (8)	0.17294 (9)	0.13454 (8)	0.0216 (3)
H51A	0.4911	0.1564	0.0941	0.026*
C52	0.59017 (9)	0.12011 (9)	0.15866 (8)	0.0229 (3)
H52A	0.5938	0.0680	0.1342	0.027*
C53	0.64505 (9)	0.14484 (9)	0.21901 (9)	0.0222 (3)
H53A	0.6860	0.1089	0.2371	0.027*
C54	0.64020 (8)	0.22249 (9)	0.25323 (8)	0.0182 (3)
H54A	0.6786	0.2381	0.2943	0.022*
C55	0.64417 (7)	0.39616 (8)	0.33197 (7)	0.0149 (3)
C56	0.71816 (7)	0.38922 (8)	0.31254 (8)	0.0166 (3)
H56A	0.7243	0.3689	0.2625	0.020*
C57	0.78282 (8)	0.41093 (8)	0.36350 (8)	0.0183 (3)
H57A	0.8318	0.4035	0.3485	0.022*
C58	0.77572 (8)	0.44333 (8)	0.43604 (8)	0.0193 (3)
H58A	0.8196	0.4572	0.4715	0.023*
C59	0.70356 (8)	0.45515 (9)	0.45582 (8)	0.0205 (3)
H59A	0.6977	0.4794	0.5044	0.025*
C60	0.63950 (8)	0.43173 (9)	0.40482 (8)	0.0186 (3)
H60A	0.5907	0.4402	0.4200	0.022*

	U11	U22	U33	U12	U13	U23
N1	0.0156 (5)	0.0144 (5)	0.0166 (5)	−0.0024 (4)	0.0024 (4)	−0.0029 (4)
N2	0.0192 (6)	0.0131 (5)	0.0168 (5)	−0.0002 (4)	0.0038 (4)	−0.0011 (4)
N3	0.0128 (5)	0.0127 (5)	0.0204 (5)	0.0001 (4)	0.0036 (4)	−0.0029 (4)
N4	0.0144 (5)	0.0099 (5)	0.0154 (5)	0.0000 (4)	0.0009 (4)	−0.0007 (4)
C1	0.0141 (6)	0.0144 (6)	0.0135 (6)	−0.0014 (5)	0.0061 (5)	−0.0028 (5)
C2	0.0220 (7)	0.0228 (7)	0.0161 (6)	0.0030 (6)	0.0009 (5)	−0.0023 (5)
C3	0.0171 (7)	0.0188 (7)	0.0290 (7)	−0.0066 (5)	0.0041 (5)	−0.0073 (6)
C4	0.0253 (7)	0.0116 (6)	0.0272 (7)	0.0014 (5)	0.0072 (6)	−0.0014 (5)
C5	0.0255 (7)	0.0260 (8)	0.0170 (6)	0.0066 (6)	0.0004 (5)	−0.0008 (6)
C6	0.0135 (6)	0.0182 (7)	0.0318 (7)	−0.0025 (5)	0.0064 (5)	−0.0047 (6)
C7	0.0167 (6)	0.0138 (6)	0.0163 (6)	0.0020 (5)	0.0022 (5)	−0.0027 (5)
C8	0.0157 (6)	0.0135 (6)	0.0164 (6)	−0.0003 (5)	0.0013 (5)	−0.0022 (5)
C9	0.0156 (6)	0.0137 (6)	0.0141 (6)	−0.0016 (5)	0.0007 (5)	−0.0031 (5)
C10	0.0192 (6)	0.0125 (6)	0.0232 (7)	−0.0039 (5)	0.0029 (5)	0.0014 (5)
C11	0.0170 (6)	0.0158 (7)	0.0222 (6)	0.0030 (5)	0.0034 (5)	−0.0036 (5)
C12	0.0219 (7)	0.0166 (6)	0.0137 (6)	0.0016 (5)	0.0001 (5)	0.0013 (5)
B1	0.0133 (6)	0.0110 (7)	0.0149 (6)	−0.0004 (5)	0.0025 (5)	0.0008 (5)
C13	0.0177 (6)	0.0116 (6)	0.0125 (5)	−0.0011 (5)	0.0028 (5)	0.0028 (5)
C14	0.0229 (7)	0.0159 (7)	0.0219 (7)	−0.0038 (5)	0.0090 (5)	−0.0007 (5)
C15	0.0356 (8)	0.0172 (7)	0.0172 (6)	−0.0076 (6)	0.0078 (6)	−0.0038 (5)
C16	0.0268 (7)	0.0189 (7)	0.0188 (6)	−0.0087 (6)	−0.0045 (5)	0.0033 (5)
C17	0.0156 (6)	0.0201 (7)	0.0266 (7)	−0.0008 (5)	−0.0004 (5)	0.0035 (6)
C18	0.0191 (6)	0.0141 (6)	0.0183 (6)	0.0003 (5)	0.0023 (5)	0.0005 (5)
C19	0.0147 (6)	0.0104 (6)	0.0147 (6)	−0.0025 (5)	0.0039 (5)	0.0018 (5)
C20	0.0151 (6)	0.0140 (6)	0.0149 (6)	−0.0019 (5)	0.0008 (5)	0.0010 (5)
C21	0.0160 (6)	0.0144 (6)	0.0215 (6)	0.0000 (5)	0.0055 (5)	−0.0001 (5)
C22	0.0212 (7)	0.0174 (7)	0.0166 (6)	−0.0047 (5)	0.0074 (5)	−0.0031 (5)
C23	0.0201 (6)	0.0197 (7)	0.0137 (6)	−0.0053 (5)	0.0023 (5)	0.0018 (5)
C24	0.0171 (6)	0.0135 (6)	0.0165 (6)	−0.0019 (5)	0.0025 (5)	0.0037 (5)
C25	0.0170 (6)	0.0122 (6)	0.0147 (6)	0.0016 (5)	0.0044 (5)	−0.0003 (5)
C26	0.0182 (6)	0.0153 (7)	0.0242 (7)	−0.0001 (5)	0.0067 (5)	0.0036 (5)
C27	0.0240 (7)	0.0147 (7)	0.0259 (7)	0.0033 (5)	0.0076 (6)	0.0062 (5)
C28	0.0190 (7)	0.0210 (7)	0.0204 (6)	0.0071 (5)	0.0030 (5)	0.0026 (5)
C29	0.0149 (6)	0.0201 (7)	0.0210 (6)	0.0004 (5)	0.0030 (5)	−0.0014 (5)
C30	0.0181 (6)	0.0132 (6)	0.0182 (6)	0.0007 (5)	0.0047 (5)	0.0011 (5)
C31	0.0105 (6)	0.0146 (6)	0.0150 (6)	−0.0004 (5)	0.0001 (4)	0.0018 (5)
C32	0.0154 (6)	0.0128 (6)	0.0197 (6)	0.0012 (5)	0.0029 (5)	0.0002 (5)
C33	0.0156 (6)	0.0215 (7)	0.0145 (6)	0.0011 (5)	0.0035 (5)	−0.0012 (5)
C34	0.0170 (6)	0.0210 (7)	0.0158 (6)	−0.0037 (5)	0.0021 (5)	0.0036 (5)
C35	0.0217 (7)	0.0153 (6)	0.0191 (6)	−0.0062 (5)	0.0012 (5)	0.0004 (5)
C36	0.0180 (6)	0.0168 (7)	0.0133 (6)	−0.0028 (5)	0.0018 (5)	−0.0019 (5)
B2	0.0127 (6)	0.0133 (7)	0.0158 (6)	−0.0006 (5)	0.0024 (5)	−0.0026 (5)
C37	0.0156 (6)	0.0146 (6)	0.0197 (6)	−0.0054 (5)	0.0041 (5)	−0.0061 (5)
C38	0.0211 (7)	0.0232 (7)	0.0204 (7)	−0.0070 (6)	0.0041 (5)	−0.0033 (6)
C39	0.0372 (9)	0.0284 (8)	0.0218 (7)	−0.0173 (7)	0.0122 (6)	−0.0069 (6)
C40	0.0298 (8)	0.0272 (8)	0.0463 (10)	−0.0156 (7)	0.0254 (7)	−0.0185 (7)
C41	0.0180 (7)	0.0207 (8)	0.0538 (10)	−0.0053 (6)	0.0144 (7)	−0.0102 (7)
C42	0.0165 (6)	0.0156 (7)	0.0324 (8)	−0.0035 (5)	0.0061 (6)	−0.0049 (6)
C43	0.0099 (6)	0.0146 (6)	0.0193 (6)	−0.0020 (5)	0.0011 (5)	−0.0014 (5)
C44	0.0148 (6)	0.0166 (7)	0.0193 (6)	−0.0011 (5)	0.0033 (5)	−0.0036 (5)
C45	0.0137 (6)	0.0151 (6)	0.0271 (7)	0.0023 (5)	0.0004 (5)	−0.0022 (5)
C46	0.0166 (6)	0.0180 (7)	0.0218 (6)	0.0029 (5)	−0.0036 (5)	0.0024 (5)
C47	0.0157 (6)	0.0225 (7)	0.0164 (6)	0.0011 (5)	−0.0012 (5)	−0.0011 (5)
C48	0.0125 (6)	0.0164 (6)	0.0183 (6)	0.0002 (5)	0.0000 (5)	−0.0035 (5)
C49	0.0164 (6)	0.0130 (6)	0.0163 (6)	−0.0028 (5)	0.0053 (5)	0.0002 (5)
C50	0.0183 (6)	0.0163 (6)	0.0198 (6)	−0.0027 (5)	0.0024 (5)	−0.0004 (5)
C51	0.0275 (7)	0.0182 (7)	0.0196 (6)	−0.0084 (6)	0.0048 (5)	−0.0030 (5)
C52	0.0335 (8)	0.0132 (6)	0.0244 (7)	−0.0037 (6)	0.0129 (6)	−0.0027 (6)
C53	0.0261 (7)	0.0143 (7)	0.0274 (7)	0.0027 (6)	0.0081 (6)	0.0034 (6)
C54	0.0201 (7)	0.0157 (6)	0.0193 (6)	−0.0004 (5)	0.0042 (5)	0.0026 (5)
C55	0.0158 (6)	0.0112 (6)	0.0173 (6)	−0.0007 (5)	0.0014 (5)	0.0006 (5)
C56	0.0174 (6)	0.0142 (6)	0.0181 (6)	−0.0008 (5)	0.0024 (5)	−0.0003 (5)
C57	0.0142 (6)	0.0145 (6)	0.0258 (7)	0.0001 (5)	0.0009 (5)	0.0023 (5)
C58	0.0212 (7)	0.0130 (6)	0.0210 (6)	−0.0028 (5)	−0.0057 (5)	0.0033 (5)
C59	0.0267 (7)	0.0171 (7)	0.0171 (6)	−0.0036 (6)	0.0015 (5)	−0.0026 (5)
C60	0.0187 (6)	0.0168 (7)	0.0205 (6)	−0.0019 (5)	0.0033 (5)	−0.0015 (5)

N1—C1	1.3390 (16)	C25—C30	1.4029 (18)
N1—C2	1.4655 (17)	C25—C26	1.4029 (18)
N1—C3	1.4671 (17)	C26—C27	1.3942 (19)
N2—C1	1.3388 (17)	C26—H26A	0.9500
N2—C5	1.4638 (17)	C27—C28	1.387 (2)
N2—C4	1.4648 (17)	C27—H27A	0.9500
N3—C1	1.3540 (17)	C28—C29	1.390 (2)
N3—C6	1.4630 (16)	C28—H28A	0.9500
N3—C7	1.4697 (17)	C29—C30	1.3928 (19)
N4—C10	1.4983 (17)	C29—H29A	0.9500
N4—C12	1.5006 (16)	C30—H30A	0.9500
N4—C11	1.5027 (16)	C31—C32	1.4039 (18)
N4—C9	1.5171 (16)	C31—C36	1.4051 (18)
C2—H2A	0.9800	C32—C33	1.3941 (19)
C2—H2B	0.9800	C32—H32A	0.9500
C2—H2C	0.9800	C33—C34	1.384 (2)
C3—H3A	0.9800	C33—H33A	0.9500
C3—H3B	0.9800	C34—C35	1.3875 (19)
C3—H3C	0.9800	C34—H34A	0.9500
C4—H4A	0.9800	C35—C36	1.3937 (19)
C4—H4B	0.9800	C35—H35A	0.9500
C4—H4C	0.9800	C36—H36A	0.9500
C5—H5A	0.9800	B2—C43	1.642 (2)
C5—H5B	0.9800	B2—C49	1.6438 (19)
C5—H5C	0.9800	B2—C55	1.6470 (19)
C6—H6A	0.9800	B2—C37	1.6471 (19)
C6—H6B	0.9800	C37—C42	1.4015 (19)
C6—H6C	0.9800	C37—C38	1.403 (2)
C7—C8	1.5389 (17)	C38—C39	1.390 (2)
C7—H7A	0.9900	C38—H38A	0.9500
C7—H7B	0.9900	C39—C40	1.388 (3)
C8—C9	1.5254 (18)	C39—H39A	0.9500
C8—H8A	0.9900	C40—C41	1.380 (3)
C8—H8B	0.9900	C40—H40A	0.9500
C9—H9A	0.9900	C41—C42	1.397 (2)
C9—H9B	0.9900	C41—H41A	0.9500
C10—H10A	0.9800	C42—H42A	0.9500
C10—H10B	0.9800	C43—C48	1.4017 (18)
C10—H10C	0.9800	C43—C44	1.4067 (18)
C11—H11A	0.9800	C44—C45	1.3911 (19)
C11—H11B	0.9800	C44—H44A	0.9500
C11—H11C	0.9800	C45—C46	1.388 (2)
C12—H12A	0.9800	C45—H45A	0.9500
C12—H12B	0.9800	C46—C47	1.387 (2)
C12—H12C	0.9800	C46—H46A	0.9500
B1—C25	1.6427 (19)	C47—C48	1.3963 (19)
B1—C19	1.6451 (19)	C47—H47A	0.9500
B1—C31	1.6584 (19)	C48—H48A	0.9500
B1—C13	1.6600 (19)	C49—C54	1.4051 (19)
C13—C18	1.4034 (18)	C49—C50	1.4088 (18)
C13—C14	1.4116 (19)	C50—C51	1.393 (2)
C14—C15	1.391 (2)	C50—H50A	0.9500
C14—H14A	0.9500	C51—C52	1.390 (2)
C15—C16	1.390 (2)	C51—H51A	0.9500
C15—H15A	0.9500	C52—C53	1.387 (2)
C16—C17	1.382 (2)	C52—H52A	0.9500
C16—H16A	0.9500	C53—C54	1.397 (2)
C17—C18	1.3955 (19)	C53—H53A	0.9500
C17—H17A	0.9500	C54—H54A	0.9500
C18—H18A	0.9500	C55—C60	1.4034 (18)
C19—C24	1.4060 (17)	C55—C56	1.4063 (18)
C19—C20	1.4089 (18)	C56—C57	1.3935 (18)
C20—C21	1.3895 (19)	C56—H56A	0.9500
C20—H20A	0.9500	C57—C58	1.387 (2)
C21—C22	1.3904 (19)	C57—H57A	0.9500
C21—H21A	0.9500	C58—C59	1.386 (2)
C22—C23	1.382 (2)	C58—H58A	0.9500
C22—H22A	0.9500	C59—C60	1.3933 (19)
C23—C24	1.3971 (19)	C59—H59A	0.9500
C23—H23A	0.9500	C60—H60A	0.9500
C24—H24A	0.9500
C1—N1—C2	122.05 (11)	C22—C23—C24	120.35 (12)
C1—N1—C3	122.97 (11)	C22—C23—H23A	119.8
C2—N1—C3	114.96 (11)	C24—C23—H23A	119.8
C1—N2—C5	121.54 (11)	C23—C24—C19	122.82 (12)
C1—N2—C4	123.64 (11)	C23—C24—H24A	118.6
C5—N2—C4	114.80 (11)	C19—C24—H24A	118.6
C1—N3—C6	120.28 (11)	C30—C25—C26	115.54 (12)
C1—N3—C7	122.04 (11)	C30—C25—B1	121.04 (11)
C6—N3—C7	117.52 (11)	C26—C25—B1	123.01 (12)
C10—N4—C12	110.16 (10)	C27—C26—C25	122.68 (13)
C10—N4—C11	108.57 (10)	C27—C26—H26A	118.7
C12—N4—C11	107.94 (10)	C25—C26—H26A	118.7
C10—N4—C9	110.79 (10)	C28—C27—C26	119.96 (13)
C12—N4—C9	110.83 (10)	C28—C27—H27A	120.0
C11—N4—C9	108.45 (10)	C26—C27—H27A	120.0
N2—C1—N1	121.12 (12)	C27—C28—C29	119.18 (13)
N2—C1—N3	118.60 (11)	C27—C28—H28A	120.4
N1—C1—N3	120.28 (12)	C29—C28—H28A	120.4
N1—C2—H2A	109.5	C28—C29—C30	119.99 (13)
N1—C2—H2B	109.5	C28—C29—H29A	120.0
H2A—C2—H2B	109.5	C30—C29—H29A	120.0
N1—C2—H2C	109.5	C29—C30—C25	122.63 (13)
H2A—C2—H2C	109.5	C29—C30—H30A	118.7
H2B—C2—H2C	109.5	C25—C30—H30A	118.7
N1—C3—H3A	109.5	C32—C31—C36	114.81 (12)
N1—C3—H3B	109.5	C32—C31—B1	121.74 (11)
H3A—C3—H3B	109.5	C36—C31—B1	123.41 (11)
N1—C3—H3C	109.5	C33—C32—C31	122.91 (13)
H3A—C3—H3C	109.5	C33—C32—H32A	118.5
H3B—C3—H3C	109.5	C31—C32—H32A	118.5
N2—C4—H4A	109.5	C34—C33—C32	120.45 (12)
N2—C4—H4B	109.5	C34—C33—H33A	119.8
H4A—C4—H4B	109.5	C32—C33—H33A	119.8
N2—C4—H4C	109.5	C33—C34—C35	118.55 (12)
H4A—C4—H4C	109.5	C33—C34—H34A	120.7
H4B—C4—H4C	109.5	C35—C34—H34A	120.7
N2—C5—H5A	109.5	C34—C35—C36	120.34 (13)
N2—C5—H5B	109.5	C34—C35—H35A	119.8
H5A—C5—H5B	109.5	C36—C35—H35A	119.8
N2—C5—H5C	109.5	C35—C36—C31	122.92 (12)
H5A—C5—H5C	109.5	C35—C36—H36A	118.5
H5B—C5—H5C	109.5	C31—C36—H36A	118.5
N3—C6—H6A	109.5	C43—B2—C49	112.26 (10)
N3—C6—H6B	109.5	C43—B2—C55	105.27 (10)
H6A—C6—H6B	109.5	C49—B2—C55	112.44 (10)
N3—C6—H6C	109.5	C43—B2—C37	110.33 (11)
H6A—C6—H6C	109.5	C49—B2—C37	106.20 (10)
H6B—C6—H6C	109.5	C55—B2—C37	110.42 (10)
N3—C7—C8	112.02 (10)	C42—C37—C38	115.43 (13)
N3—C7—H7A	109.2	C42—C37—B2	124.38 (12)
C8—C7—H7A	109.2	C38—C37—B2	120.19 (12)
N3—C7—H7B	109.2	C39—C38—C37	122.67 (14)
C8—C7—H7B	109.2	C39—C38—H38A	118.7
H7A—C7—H7B	107.9	C37—C38—H38A	118.7
C9—C8—C7	108.24 (10)	C40—C39—C38	120.02 (15)
C9—C8—H8A	110.1	C40—C39—H39A	120.0
C7—C8—H8A	110.1	C38—C39—H39A	120.0
C9—C8—H8B	110.1	C41—C40—C39	119.05 (14)
C7—C8—H8B	110.1	C41—C40—H40A	120.5
H8A—C8—H8B	108.4	C39—C40—H40A	120.5
N4—C9—C8	115.25 (10)	C40—C41—C42	120.28 (15)
N4—C9—H9A	108.5	C40—C41—H41A	119.9
C8—C9—H9A	108.5	C42—C41—H41A	119.9
N4—C9—H9B	108.5	C41—C42—C37	122.35 (15)
C8—C9—H9B	108.5	C41—C42—H42A	118.8
H9A—C9—H9B	107.5	C37—C42—H42A	118.8
N4—C10—H10A	109.5	C48—C43—C44	115.20 (12)
N4—C10—H10B	109.5	C48—C43—B2	125.02 (12)
H10A—C10—H10B	109.5	C44—C43—B2	119.76 (11)
N4—C10—H10C	109.5	C45—C44—C43	123.25 (12)
H10A—C10—H10C	109.5	C45—C44—H44A	118.4
H10B—C10—H10C	109.5	C43—C44—H44A	118.4
N4—C11—H11A	109.5	C46—C45—C44	119.58 (13)
N4—C11—H11B	109.5	C46—C45—H45A	120.2
H11A—C11—H11B	109.5	C44—C45—H45A	120.2
N4—C11—H11C	109.5	C47—C46—C45	119.10 (13)
H11A—C11—H11C	109.5	C47—C46—H46A	120.5
H11B—C11—H11C	109.5	C45—C46—H46A	120.5
N4—C12—H12A	109.5	C46—C47—C48	120.43 (13)
N4—C12—H12B	109.5	C46—C47—H47A	119.8
H12A—C12—H12B	109.5	C48—C47—H47A	119.8
N4—C12—H12C	109.5	C47—C48—C43	122.32 (13)
H12A—C12—H12C	109.5	C47—C48—H48A	118.8
H12B—C12—H12C	109.5	C43—C48—H48A	118.8
C25—B1—C19	108.02 (10)	C54—C49—C50	115.02 (12)
C25—B1—C31	108.60 (10)	C54—C49—B2	125.40 (11)
C19—B1—C31	109.35 (10)	C50—C49—B2	119.43 (12)
C25—B1—C13	110.74 (10)	C51—C50—C49	122.77 (13)
C19—B1—C13	111.30 (10)	C51—C50—H50A	118.6
C31—B1—C13	108.78 (10)	C49—C50—H50A	118.6
C18—C13—C14	114.15 (12)	C52—C51—C50	120.28 (13)
C18—C13—B1	123.89 (12)	C52—C51—H51A	119.9
C14—C13—B1	121.89 (11)	C50—C51—H51A	119.9
C15—C14—C13	123.02 (13)	C53—C52—C51	118.84 (13)
C15—C14—H14A	118.5	C53—C52—H52A	120.6
C13—C14—H14A	118.5	C51—C52—H52A	120.6
C16—C15—C14	120.59 (13)	C52—C53—C54	120.16 (13)
C16—C15—H15A	119.7	C52—C53—H53A	119.9
C14—C15—H15A	119.7	C54—C53—H53A	119.9
C17—C16—C15	118.31 (13)	C53—C54—C49	122.90 (13)
C17—C16—H16A	120.8	C53—C54—H54A	118.6
C15—C16—H16A	120.8	C49—C54—H54A	118.6
C16—C17—C18	120.38 (13)	C60—C55—C56	115.11 (12)
C16—C17—H17A	119.8	C60—C55—B2	123.72 (12)
C18—C17—H17A	119.8	C56—C55—B2	121.08 (11)
C17—C18—C13	123.41 (13)	C57—C56—C55	122.83 (13)
C17—C18—H18A	118.3	C57—C56—H56A	118.6
C13—C18—H18A	118.3	C55—C56—H56A	118.6
C24—C19—C20	114.76 (12)	C58—C57—C56	120.06 (13)
C24—C19—B1	123.37 (11)	C58—C57—H57A	120.0
C20—C19—B1	121.83 (11)	C56—C57—H57A	120.0
C21—C20—C19	123.05 (12)	C59—C58—C57	118.84 (12)
C21—C20—H20A	118.5	C59—C58—H58A	120.6
C19—C20—H20A	118.5	C57—C58—H58A	120.6
C20—C21—C22	120.20 (13)	C58—C59—C60	120.40 (13)
C20—C21—H21A	119.9	C58—C59—H59A	119.8
C22—C21—H21A	119.9	C60—C59—H59A	119.8
C23—C22—C21	118.81 (12)	C59—C60—C55	122.62 (13)
C23—C22—H22A	120.6	C59—C60—H60A	118.7
C21—C22—H22A	120.6	C55—C60—H60A	118.7
C5—N2—C1—N1	−150.00 (13)	C13—B1—C31—C36	131.83 (12)
C4—N2—C1—N1	31.57 (19)	C36—C31—C32—C33	−1.25 (18)
C5—N2—C1—N3	29.97 (18)	B1—C31—C32—C33	−179.20 (12)
C4—N2—C1—N3	−148.46 (12)	C31—C32—C33—C34	0.1 (2)
C2—N1—C1—N2	−150.60 (12)	C32—C33—C34—C35	1.2 (2)
C3—N1—C1—N2	27.44 (19)	C33—C34—C35—C36	−1.3 (2)
C2—N1—C1—N3	29.43 (18)	C34—C35—C36—C31	0.1 (2)
C3—N1—C1—N3	−152.53 (12)	C32—C31—C36—C35	1.12 (19)
C6—N3—C1—N2	44.91 (17)	B1—C31—C36—C35	179.04 (12)
C7—N3—C1—N2	−139.78 (12)	C43—B2—C37—C42	12.69 (17)
C6—N3—C1—N1	−135.12 (13)	C49—B2—C37—C42	−109.20 (14)
C7—N3—C1—N1	40.19 (18)	C55—B2—C37—C42	128.64 (13)
C1—N3—C7—C8	122.96 (13)	C43—B2—C37—C38	−167.47 (12)
C6—N3—C7—C8	−61.61 (15)	C49—B2—C37—C38	70.64 (15)
N3—C7—C8—C9	−160.81 (11)	C55—B2—C37—C38	−51.52 (16)
C10—N4—C9—C8	71.23 (14)	C42—C37—C38—C39	−4.5 (2)
C12—N4—C9—C8	−51.38 (14)	B2—C37—C38—C39	175.68 (13)
C11—N4—C9—C8	−169.70 (11)	C37—C38—C39—C40	1.2 (2)
C7—C8—C9—N4	−170.40 (10)	C38—C39—C40—C41	2.5 (2)
C25—B1—C13—C18	137.19 (12)	C39—C40—C41—C42	−2.7 (2)
C19—B1—C13—C18	17.01 (17)	C40—C41—C42—C37	−0.8 (2)
C31—B1—C13—C18	−103.53 (14)	C38—C37—C42—C41	4.2 (2)
C25—B1—C13—C14	−46.18 (16)	B2—C37—C42—C41	−175.91 (13)
C19—B1—C13—C14	−166.35 (11)	C49—B2—C43—C48	−14.96 (17)
C31—B1—C13—C14	73.10 (15)	C55—B2—C43—C48	107.68 (13)
C18—C13—C14—C15	4.09 (19)	C37—B2—C43—C48	−133.20 (12)
B1—C13—C14—C15	−172.85 (12)	C49—B2—C43—C44	166.63 (11)
C13—C14—C15—C16	−1.8 (2)	C55—B2—C43—C44	−70.74 (14)
C14—C15—C16—C17	−1.4 (2)	C37—B2—C43—C44	48.39 (15)
C15—C16—C17—C18	2.0 (2)	C48—C43—C44—C45	3.72 (19)
C16—C17—C18—C13	0.5 (2)	B2—C43—C44—C45	−177.71 (12)
C14—C13—C18—C17	−3.47 (19)	C43—C44—C45—C46	−3.1 (2)
B1—C13—C18—C17	173.40 (12)	C44—C45—C46—C47	−0.1 (2)
C25—B1—C19—C24	−3.37 (16)	C45—C46—C47—C48	2.4 (2)
C31—B1—C19—C24	−121.39 (13)	C46—C47—C48—C43	−1.7 (2)
C13—B1—C19—C24	118.40 (13)	C44—C43—C48—C47	−1.27 (18)
C25—B1—C19—C20	174.10 (11)	B2—C43—C48—C47	−179.75 (12)
C31—B1—C19—C20	56.08 (15)	C43—B2—C49—C54	129.63 (13)
C13—B1—C19—C20	−64.13 (15)	C55—B2—C49—C54	11.14 (18)
C24—C19—C20—C21	0.12 (19)	C37—B2—C49—C54	−109.72 (14)
B1—C19—C20—C21	−177.55 (12)	C43—B2—C49—C50	−55.04 (15)
C19—C20—C21—C22	−1.0 (2)	C55—B2—C49—C50	−173.52 (11)
C20—C21—C22—C23	1.0 (2)	C37—B2—C49—C50	65.62 (15)
C21—C22—C23—C24	−0.2 (2)	C54—C49—C50—C51	−1.45 (19)
C22—C23—C24—C19	−0.8 (2)	B2—C49—C50—C51	−177.25 (12)
C20—C19—C24—C23	0.77 (19)	C49—C50—C51—C52	0.2 (2)
B1—C19—C24—C23	178.40 (12)	C50—C51—C52—C53	1.4 (2)
C19—B1—C25—C30	−79.63 (14)	C51—C52—C53—C54	−1.6 (2)
C31—B1—C25—C30	38.87 (16)	C52—C53—C54—C49	0.3 (2)
C13—B1—C25—C30	158.26 (11)	C50—C49—C54—C53	1.20 (19)
C19—B1—C25—C26	92.75 (14)	B2—C49—C54—C53	176.72 (13)
C31—B1—C25—C26	−148.75 (12)	C43—B2—C55—C60	100.23 (14)
C13—B1—C25—C26	−29.36 (17)	C49—B2—C55—C60	−137.25 (13)
C30—C25—C26—C27	−0.1 (2)	C37—B2—C55—C60	−18.83 (17)
B1—C25—C26—C27	−172.88 (13)	C43—B2—C55—C56	−76.22 (15)
C25—C26—C27—C28	0.8 (2)	C49—B2—C55—C56	46.29 (16)
C26—C27—C28—C29	−0.6 (2)	C37—B2—C55—C56	164.71 (12)
C27—C28—C29—C30	−0.1 (2)	C60—C55—C56—C57	4.0 (2)
C28—C29—C30—C25	0.8 (2)	B2—C55—C56—C57	−179.26 (12)
C26—C25—C30—C29	−0.66 (19)	C55—C56—C57—C58	−2.1 (2)
B1—C25—C30—C29	172.25 (12)	C56—C57—C58—C59	−1.4 (2)
C25—B1—C31—C32	70.22 (14)	C57—C58—C59—C60	2.6 (2)
C19—B1—C31—C32	−172.13 (11)	C58—C59—C60—C55	−0.4 (2)
C13—B1—C31—C32	−50.39 (15)	C56—C55—C60—C59	−2.8 (2)
C25—B1—C31—C36	−107.56 (13)	B2—C55—C60—C59	−179.40 (13)
C19—B1—C31—C36	10.09 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3C···Cg7	0.98	2.62	3.3783 (16)	134
C7—H7B···Cg1	0.99	2.80	3.7805 (14)	169
C9—H9B···Cg6	0.99	2.52	3.4075 (14)	149
C11—H11C···Cg5i	0.98	2.62	3.4852 (15)	147
C12—H12A···Cg4	0.98	2.59	3.4044 (15)	141
C12—H12B···Cg8ii	0.98	2.69	3.5990 (15)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg4, Cg5, Cg6, and Cg8 are the centroids of the C13–C18,C31–C36, C37–C42, C43–C48 and C55–C60 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3C⋯Cg7	0.98	2.62	3.3783 (16)	134
C7—H7B⋯Cg1	0.99	2.80	3.7805 (14)	169
C9—H9B⋯Cg6	0.99	2.52	3.4075 (14)	149
C11—H11C⋯Cg5i	0.98	2.62	3.4852 (15)	147
C12—H12A⋯Cg4	0.98	2.59	3.4044 (15)	141
C12—H12B⋯Cg8ii	0.98	2.69	3.5990 (15)	155

Symmetry codes: (i) ; (ii) .