N-[3-(Di-methyl-amino)-prop-yl]-N,N',N',N'',N''-penta-methyl-guanidinium tetra-phenyl-borate.

In the title salt, C11H27N4 (+)·C24H20B(-), the C-N bond lengths in the central CN3 unit of the guanidinium ion are 1.333 (4), 1.334 (4) and 1.351 (4) Å, indicating partial double-bond character. The C atom of this unit is bonded to the three N atoms in a nearly ideal trigonal-planar geometry [N-C-N angles = 118.8 (3), 120.0 (3) and 121.2 (3)°] and the positive charge is delocalized in the CN3 plane. The bonds between the N atoms and the terminal C-methyl groups of the guanidinium moiety have values in the range 1.459 (4)-1.478 (4) Å, close to a typical single bond. In the crystal, there are C-H⋯π inter-actions between the guanidinium H atoms and the phenyl rings of the tetra-phenyl-borate ion. These inter-actions combine to form a ladder of linked chains of ions which runs parallel to the c axis.

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 ▶). For the crystal structure of N,N,N′,N′,N′′-tetra­methyl-N′′-[3-(tri­methyl­aza­nium­yl)prop­yl]guanid­in­ium bis­(tetra­phenyl­borate) acetone disolvate, see: Tiritiris (2013 ▶).

Experimental

Crystal data

C11H27N4 +·C24H20B−

M = 534.58

Orthorhombic,

a = 20.5074 (7) Å

b = 15.4134 (5) Å

c = 9.8568 (3) Å

V = 3115.62 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.20 × 0.18 × 0.13 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

7338 measured reflections

4035 independent reflections

3181 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.137

S = 1.05

4035 reflections

368 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.48 e Å−3

Δρmin = −0.20 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014906/go2091sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014906/go2091Isup2.hkl

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

C11H27N4+·C24H20B−	F(000) = 1160
Mr = 534.58	Dx = 1.140 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 4121 reflections
a = 20.5074 (7) Å	θ = 0.4–28.3°
b = 15.4134 (5) Å	µ = 0.07 mm−1
c = 9.8568 (3) Å	T = 100 K
V = 3115.62 (17) Å3	Block, colorless
Z = 4	0.20 × 0.18 × 0.13 mm

Bruker–Nonius KappaCCD diffractometer	3181 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.049
Graphite monochromator	θmax = 28.3°, θmin = 2.7°
φ scans, and ω scans	h = −27→27
7338 measured reflections	k = −20→20
4035 independent reflections	l = −13→12

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)] = 0.057	Hydrogen site location: difference Fourier map
wR(F2) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0694P)2 + 1.0225P] where P = (Fo2 + 2Fc2)/3
4035 reflections	(Δ/σ)max < 0.001
368 parameters	Δρmax = 0.48 e Å−3
1 restraint	Δρmin = −0.20 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	0.39908 (13)	0.30671 (18)	0.1123 (3)	0.0180 (6)
N1	0.45724 (13)	0.34774 (16)	0.1064 (3)	0.0244 (6)
N2	0.35484 (13)	0.32310 (18)	0.0164 (3)	0.0268 (6)
N3	0.38671 (13)	0.25113 (19)	0.2126 (3)	0.0286 (6)
C2	0.48919 (16)	0.3777 (2)	0.2309 (3)	0.0264 (7)
H2A	0.4590	0.3721	0.3074	0.040*
H2B	0.5019	0.4387	0.2205	0.040*
H2C	0.5281	0.3425	0.2480	0.040*
C3	0.48916 (15)	0.3656 (2)	−0.0229 (3)	0.0239 (7)
H3A	0.4658	0.3357	−0.0960	0.036*
H3B	0.5343	0.3449	−0.0196	0.036*
H3C	0.4888	0.4282	−0.0400	0.036*
C4	0.34857 (17)	0.4102 (2)	−0.0391 (4)	0.0289 (7)
H4A	0.3756	0.4504	0.0136	0.043*
H4B	0.3029	0.4286	−0.0344	0.043*
H4C	0.3630	0.4104	−0.1339	0.043*
C5	0.30700 (16)	0.2586 (2)	−0.0301 (4)	0.0322 (8)
H5A	0.3196	0.2010	0.0029	0.048*
H5B	0.3057	0.2583	−0.1295	0.048*
H5C	0.2638	0.2736	0.0054	0.048*
C6	0.32119 (17)	0.2457 (3)	0.2736 (4)	0.0354 (8)
H6A	0.2932	0.2908	0.2345	0.053*
H6B	0.3244	0.2542	0.3719	0.053*
H6C	0.3023	0.1885	0.2548	0.053*
C7	0.43937 (16)	0.2002 (2)	0.2769 (4)	0.0306 (7)
H7A	0.4467	0.2219	0.3702	0.037*
H7B	0.4803	0.2084	0.2250	0.037*
C8	0.42283 (19)	0.1043 (2)	0.2822 (4)	0.0373 (9)
H8A	0.3845	0.0964	0.3421	0.045*
H8B	0.4599	0.0730	0.3239	0.045*
C9	0.40794 (19)	0.0629 (2)	0.1454 (4)	0.0391 (9)
H9A	0.4075	−0.0010	0.1563	0.047*
H9B	0.3638	0.0810	0.1163	0.047*
N4	0.45421 (17)	0.08554 (19)	0.0396 (3)	0.0390 (8)
C10	0.5176 (2)	0.0427 (3)	0.0700 (5)	0.0482 (11)
H10A	0.5113	−0.0203	0.0750	0.072*
H10B	0.5344	0.0639	0.1569	0.072*
H10C	0.5490	0.0561	−0.0021	0.072*
C11	0.4322 (2)	0.0575 (3)	−0.0917 (4)	0.0491 (11)
H11A	0.4265	−0.0057	−0.0913	0.074*
H11B	0.4645	0.0735	−0.1604	0.074*
H11C	0.3905	0.0854	−0.1128	0.074*
B1	0.12881 (15)	0.2061 (2)	0.5818 (3)	0.0159 (6)
C12	0.16933 (14)	0.12719 (18)	0.6527 (3)	0.0173 (6)
C13	0.14514 (15)	0.07030 (18)	0.7512 (3)	0.0209 (6)
H13	0.1010	0.0762	0.7787	0.025*
C14	0.18295 (16)	0.0051 (2)	0.8113 (3)	0.0270 (7)
H14	0.1642	−0.0323	0.8773	0.032*
C15	0.24774 (17)	−0.0048 (2)	0.7742 (4)	0.0324 (8)
H15	0.2736	−0.0492	0.8136	0.039*
C16	0.27425 (17)	0.0512 (2)	0.6787 (4)	0.0328 (8)
H16	0.3187	0.0453	0.6529	0.039*
C17	0.23622 (14)	0.1154 (2)	0.6208 (3)	0.0246 (7)
H17	0.2558	0.1534	0.5568	0.029*
C18	0.04911 (14)	0.19818 (17)	0.6052 (3)	0.0177 (6)
C19	0.00849 (14)	0.26899 (19)	0.6360 (3)	0.0220 (6)
H19	0.0278	0.3242	0.6509	0.026*
C20	−0.05945 (15)	0.2613 (2)	0.6456 (4)	0.0271 (7)
H20	−0.0851	0.3108	0.6668	0.033*
C21	−0.08949 (15)	0.1820 (2)	0.6244 (4)	0.0272 (7)
H21	−0.1355	0.1766	0.6312	0.033*
C22	−0.05143 (15)	0.1109 (2)	0.5932 (3)	0.0254 (7)
H22	−0.0713	0.0560	0.5783	0.031*
C23	0.01633 (14)	0.11928 (19)	0.5835 (3)	0.0212 (6)
H23	0.0413	0.0694	0.5612	0.025*
C24	0.15858 (13)	0.29536 (17)	0.6477 (3)	0.0158 (6)
C25	0.20552 (14)	0.34705 (18)	0.5837 (3)	0.0213 (6)
H25	0.2196	0.3312	0.4953	0.026*
C26	0.23223 (14)	0.4200 (2)	0.6432 (3)	0.0242 (7)
H26	0.2633	0.4535	0.5946	0.029*
C27	0.21415 (14)	0.44452 (19)	0.7727 (3)	0.0233 (6)
H27	0.2320	0.4951	0.8132	0.028*
C28	0.16949 (14)	0.39393 (19)	0.8422 (3)	0.0211 (6)
H28	0.1573	0.4090	0.9322	0.025*
C29	0.14233 (14)	0.32109 (18)	0.7808 (3)	0.0192 (6)
H29	0.1117	0.2874	0.8304	0.023*
C30	0.13792 (14)	0.20459 (18)	0.4149 (3)	0.0167 (6)
C31	0.15854 (14)	0.13116 (19)	0.3429 (3)	0.0186 (6)
H31	0.1696	0.0804	0.3925	0.022*
C32	0.16356 (15)	0.1292 (2)	0.2026 (3)	0.0237 (7)
H32	0.1767	0.0772	0.1586	0.028*
C33	0.14963 (14)	0.2019 (2)	0.1260 (3)	0.0241 (7)
H33	0.1541	0.2013	0.0301	0.029*
C34	0.12899 (16)	0.2758 (2)	0.1937 (3)	0.0274 (7)
H34	0.1188	0.3265	0.1431	0.033*
C35	0.12292 (15)	0.27719 (19)	0.3343 (3)	0.0234 (7)
H35	0.1082	0.3288	0.3772	0.028*

	U11	U22	U33	U12	U13	U23
C1	0.0173 (13)	0.0200 (13)	0.0165 (14)	0.0010 (11)	0.0008 (11)	0.0009 (12)
N1	0.0237 (13)	0.0283 (13)	0.0213 (13)	0.0020 (11)	−0.0011 (11)	0.0011 (12)
N2	0.0239 (14)	0.0282 (13)	0.0283 (15)	−0.0020 (11)	−0.0049 (12)	0.0045 (12)
N3	0.0209 (13)	0.0362 (15)	0.0288 (14)	0.0002 (12)	−0.0016 (12)	0.0066 (13)
C2	0.0236 (16)	0.0304 (17)	0.0252 (17)	0.0002 (14)	−0.0095 (13)	−0.0042 (14)
C3	0.0219 (15)	0.0306 (16)	0.0194 (15)	0.0012 (13)	0.0012 (12)	0.0044 (13)
C4	0.0316 (17)	0.0265 (16)	0.0286 (17)	0.0045 (14)	−0.0103 (14)	0.0040 (14)
C5	0.0233 (16)	0.0365 (18)	0.0370 (19)	−0.0069 (15)	−0.0103 (15)	−0.0019 (16)
C6	0.0273 (17)	0.051 (2)	0.0280 (17)	−0.0036 (16)	0.0070 (15)	0.0051 (18)
C7	0.0288 (17)	0.0380 (18)	0.0250 (16)	0.0079 (14)	−0.0015 (14)	0.0122 (16)
C8	0.0383 (19)	0.0395 (19)	0.034 (2)	0.0062 (16)	0.0064 (17)	0.0152 (17)
C9	0.042 (2)	0.0292 (17)	0.046 (2)	−0.0023 (16)	0.0041 (19)	0.0113 (18)
N4	0.054 (2)	0.0276 (15)	0.0353 (17)	−0.0149 (15)	0.0125 (15)	0.0025 (13)
C10	0.042 (2)	0.054 (2)	0.049 (3)	−0.015 (2)	0.0106 (19)	−0.006 (2)
C11	0.062 (3)	0.039 (2)	0.045 (3)	0.001 (2)	0.002 (2)	0.003 (2)
B1	0.0161 (14)	0.0141 (14)	0.0176 (16)	−0.0001 (12)	−0.0008 (12)	0.0019 (13)
C12	0.0186 (14)	0.0176 (13)	0.0158 (14)	−0.0030 (11)	−0.0029 (11)	0.0021 (11)
C13	0.0238 (15)	0.0208 (14)	0.0182 (16)	0.0007 (12)	0.0009 (12)	0.0040 (12)
C14	0.0327 (17)	0.0276 (15)	0.0206 (16)	−0.0004 (14)	−0.0018 (13)	0.0096 (13)
C15	0.0340 (18)	0.0330 (17)	0.0302 (17)	0.0073 (15)	−0.0065 (15)	0.0133 (16)
C16	0.0231 (16)	0.0389 (19)	0.036 (2)	0.0029 (15)	−0.0030 (14)	0.0091 (16)
C17	0.0180 (14)	0.0280 (15)	0.0277 (17)	0.0012 (12)	−0.0050 (13)	0.0097 (14)
C18	0.0195 (13)	0.0180 (13)	0.0156 (14)	0.0008 (11)	−0.0025 (12)	0.0024 (11)
C19	0.0184 (14)	0.0198 (13)	0.0278 (16)	−0.0014 (11)	−0.0039 (13)	0.0023 (13)
C20	0.0187 (15)	0.0292 (16)	0.0335 (18)	0.0067 (13)	−0.0038 (14)	0.0030 (15)
C21	0.0155 (13)	0.0408 (17)	0.0254 (17)	−0.0022 (13)	−0.0013 (13)	0.0053 (15)
C22	0.0241 (15)	0.0283 (15)	0.0239 (16)	−0.0128 (13)	−0.0002 (13)	0.0014 (14)
C23	0.0196 (14)	0.0205 (14)	0.0236 (16)	−0.0039 (12)	0.0026 (12)	−0.0019 (12)
C24	0.0116 (12)	0.0169 (12)	0.0188 (14)	0.0024 (10)	−0.0028 (11)	0.0037 (11)
C25	0.0185 (14)	0.0218 (14)	0.0235 (16)	−0.0036 (12)	0.0024 (12)	−0.0070 (13)
C26	0.0182 (14)	0.0263 (15)	0.0282 (17)	−0.0060 (12)	0.0015 (13)	−0.0022 (14)
C27	0.0192 (14)	0.0234 (14)	0.0273 (16)	−0.0023 (12)	−0.0078 (14)	−0.0056 (14)
C28	0.0226 (14)	0.0260 (15)	0.0148 (14)	0.0019 (12)	−0.0040 (12)	−0.0027 (12)
C29	0.0162 (13)	0.0213 (13)	0.0202 (15)	0.0004 (11)	−0.0023 (12)	0.0031 (13)
C30	0.0140 (13)	0.0167 (13)	0.0193 (14)	−0.0050 (11)	−0.0014 (11)	0.0029 (12)
C31	0.0187 (14)	0.0148 (13)	0.0223 (15)	0.0010 (11)	−0.0001 (12)	0.0021 (12)
C32	0.0193 (15)	0.0291 (16)	0.0228 (16)	0.0027 (13)	0.0013 (12)	−0.0035 (14)
C33	0.0171 (13)	0.0365 (17)	0.0188 (15)	−0.0040 (12)	−0.0024 (12)	0.0027 (14)
C34	0.0269 (17)	0.0299 (17)	0.0254 (17)	−0.0030 (14)	−0.0051 (13)	0.0138 (14)
C35	0.0286 (16)	0.0162 (14)	0.0253 (17)	0.0045 (13)	−0.0024 (13)	0.0040 (13)

C1—N3	1.333 (4)	C12—C13	1.400 (4)
C1—N2	1.334 (4)	C12—C17	1.419 (4)
C1—N1	1.351 (4)	C13—C14	1.401 (4)
N1—C3	1.459 (4)	C13—H13	0.9500
N1—C2	1.466 (4)	C14—C15	1.386 (5)
N2—C4	1.456 (4)	C14—H14	0.9500
N2—C5	1.470 (4)	C15—C16	1.387 (5)
N3—C6	1.474 (4)	C15—H15	0.9500
N3—C7	1.478 (4)	C16—C17	1.384 (4)
C2—H2A	0.9800	C16—H16	0.9500
C2—H2B	0.9800	C17—H17	0.9500
C2—H2C	0.9800	C18—C23	1.406 (4)
C3—H3A	0.9800	C18—C19	1.406 (4)
C3—H3B	0.9800	C19—C20	1.402 (4)
C3—H3C	0.9800	C19—H19	0.9500
C4—H4A	0.9800	C20—C21	1.385 (5)
C4—H4B	0.9800	C20—H20	0.9500
C4—H4C	0.9800	C21—C22	1.380 (5)
C5—H5A	0.9800	C21—H21	0.9500
C5—H5B	0.9800	C22—C23	1.399 (4)
C5—H5C	0.9800	C22—H22	0.9500
C6—H6A	0.9800	C23—H23	0.9500
C6—H6B	0.9800	C24—C25	1.400 (4)
C6—H6C	0.9800	C24—C29	1.410 (4)
C7—C8	1.518 (5)	C25—C26	1.381 (4)
C7—H7A	0.9900	C25—H25	0.9500
C7—H7B	0.9900	C26—C27	1.382 (5)
C8—C9	1.523 (6)	C26—H26	0.9500
C8—H8A	0.9900	C27—C28	1.384 (4)
C8—H8B	0.9900	C27—H27	0.9500
C9—N4	1.453 (5)	C28—C29	1.392 (4)
C9—H9A	0.9900	C28—H28	0.9500
C9—H9B	0.9900	C29—H29	0.9500
N4—C11	1.437 (6)	C30—C31	1.401 (4)
N4—C10	1.489 (6)	C30—C35	1.407 (4)
C10—H10A	0.9800	C31—C32	1.387 (4)
C10—H10B	0.9800	C31—H31	0.9500
C10—H10C	0.9800	C32—C33	1.382 (5)
C11—H11A	0.9800	C32—H32	0.9500
C11—H11B	0.9800	C33—C34	1.386 (5)
C11—H11C	0.9800	C33—H33	0.9500
B1—C12	1.630 (4)	C34—C35	1.392 (5)
B1—C24	1.640 (4)	C34—H34	0.9500
B1—C18	1.655 (4)	C35—H35	0.9500
B1—C30	1.656 (4)
N3—C1—N2	121.2 (3)	C24—B1—C18	112.0 (2)
N3—C1—N1	120.0 (3)	C12—B1—C30	111.0 (2)
N2—C1—N1	118.8 (3)	C24—B1—C30	111.3 (2)
C1—N1—C3	121.5 (3)	C18—B1—C30	104.4 (2)
C1—N1—C2	120.4 (3)	C13—C12—C17	114.6 (3)
C3—N1—C2	118.1 (2)	C13—C12—B1	125.7 (3)
C1—N2—C4	120.1 (3)	C17—C12—B1	119.6 (2)
C1—N2—C5	123.1 (3)	C12—C13—C14	123.2 (3)
C4—N2—C5	116.6 (3)	C12—C13—H13	118.4
C1—N3—C6	120.8 (3)	C14—C13—H13	118.4
C1—N3—C7	121.4 (3)	C15—C14—C13	119.8 (3)
C6—N3—C7	117.5 (3)	C15—C14—H14	120.1
N1—C2—H2A	109.5	C13—C14—H14	120.1
N1—C2—H2B	109.5	C14—C15—C16	119.1 (3)
H2A—C2—H2B	109.5	C14—C15—H15	120.5
N1—C2—H2C	109.5	C16—C15—H15	120.5
H2A—C2—H2C	109.5	C17—C16—C15	120.3 (3)
H2B—C2—H2C	109.5	C17—C16—H16	119.9
N1—C3—H3A	109.5	C15—C16—H16	119.9
N1—C3—H3B	109.5	C16—C17—C12	123.0 (3)
H3A—C3—H3B	109.5	C16—C17—H17	118.5
N1—C3—H3C	109.5	C12—C17—H17	118.5
H3A—C3—H3C	109.5	C23—C18—C19	114.9 (3)
H3B—C3—H3C	109.5	C23—C18—B1	121.0 (2)
N2—C4—H4A	109.5	C19—C18—B1	123.9 (2)
N2—C4—H4B	109.5	C20—C19—C18	122.5 (3)
H4A—C4—H4B	109.5	C20—C19—H19	118.7
N2—C4—H4C	109.5	C18—C19—H19	118.7
H4A—C4—H4C	109.5	C21—C20—C19	120.5 (3)
H4B—C4—H4C	109.5	C21—C20—H20	119.8
N2—C5—H5A	109.5	C19—C20—H20	119.8
N2—C5—H5B	109.5	C22—C21—C20	118.9 (3)
H5A—C5—H5B	109.5	C22—C21—H21	120.6
N2—C5—H5C	109.5	C20—C21—H21	120.6
H5A—C5—H5C	109.5	C21—C22—C23	120.2 (3)
H5B—C5—H5C	109.5	C21—C22—H22	119.9
N3—C6—H6A	109.5	C23—C22—H22	119.9
N3—C6—H6B	109.5	C22—C23—C18	123.0 (3)
H6A—C6—H6B	109.5	C22—C23—H23	118.5
N3—C6—H6C	109.5	C18—C23—H23	118.5
H6A—C6—H6C	109.5	C25—C24—C29	115.0 (3)
H6B—C6—H6C	109.5	C25—C24—B1	123.7 (3)
N3—C7—C8	111.6 (3)	C29—C24—B1	121.1 (2)
N3—C7—H7A	109.3	C26—C25—C24	123.0 (3)
C8—C7—H7A	109.3	C26—C25—H25	118.5
N3—C7—H7B	109.3	C24—C25—H25	118.5
C8—C7—H7B	109.3	C25—C26—C27	120.6 (3)
H7A—C7—H7B	108.0	C25—C26—H26	119.7
C7—C8—C9	115.0 (3)	C27—C26—H26	119.7
C7—C8—H8A	108.5	C26—C27—C28	118.7 (3)
C9—C8—H8A	108.5	C26—C27—H27	120.6
C7—C8—H8B	108.5	C28—C27—H27	120.6
C9—C8—H8B	108.5	C27—C28—C29	120.3 (3)
H8A—C8—H8B	107.5	C27—C28—H28	119.9
N4—C9—C8	113.8 (3)	C29—C28—H28	119.9
N4—C9—H9A	108.8	C28—C29—C24	122.5 (3)
C8—C9—H9A	108.8	C28—C29—H29	118.8
N4—C9—H9B	108.8	C24—C29—H29	118.8
C8—C9—H9B	108.8	C31—C30—C35	115.0 (3)
H9A—C9—H9B	107.7	C31—C30—B1	123.3 (3)
C11—N4—C9	111.6 (3)	C35—C30—B1	121.7 (3)
C11—N4—C10	108.8 (3)	C32—C31—C30	123.0 (3)
C9—N4—C10	108.6 (3)	C32—C31—H31	118.5
N4—C10—H10A	109.5	C30—C31—H31	118.5
N4—C10—H10B	109.5	C33—C32—C31	120.7 (3)
H10A—C10—H10B	109.5	C33—C32—H32	119.6
N4—C10—H10C	109.5	C31—C32—H32	119.6
H10A—C10—H10C	109.5	C32—C33—C34	117.9 (3)
H10B—C10—H10C	109.5	C32—C33—H33	121.1
N4—C11—H11A	109.5	C34—C33—H33	121.1
N4—C11—H11B	109.5	C33—C34—C35	121.2 (3)
H11A—C11—H11B	109.5	C33—C34—H34	119.4
N4—C11—H11C	109.5	C35—C34—H34	119.4
H11A—C11—H11C	109.5	C34—C35—C30	122.1 (3)
H11B—C11—H11C	109.5	C34—C35—H35	119.0
C12—B1—C24	105.4 (2)	C30—C35—H35	119.0
C12—B1—C18	112.9 (2)
N3—C1—N1—C3	143.5 (3)	C30—B1—C18—C19	−101.0 (3)
N2—C1—N1—C3	−36.6 (4)	C23—C18—C19—C20	0.6 (5)
N3—C1—N1—C2	−38.2 (4)	B1—C18—C19—C20	175.3 (3)
N2—C1—N1—C2	141.7 (3)	C18—C19—C20—C21	−0.1 (5)
N3—C1—N2—C4	143.5 (3)	C19—C20—C21—C22	−0.2 (5)
N1—C1—N2—C4	−36.4 (4)	C20—C21—C22—C23	0.0 (5)
N3—C1—N2—C5	−31.1 (5)	C21—C22—C23—C18	0.5 (5)
N1—C1—N2—C5	149.0 (3)	C19—C18—C23—C22	−0.8 (5)
N2—C1—N3—C6	−37.1 (5)	B1—C18—C23—C22	−175.6 (3)
N1—C1—N3—C6	142.8 (3)	C12—B1—C24—C25	98.6 (3)
N2—C1—N3—C7	149.9 (3)	C18—B1—C24—C25	−138.3 (3)
N1—C1—N3—C7	−30.2 (4)	C30—B1—C24—C25	−21.8 (4)
C1—N3—C7—C8	−129.3 (3)	C12—B1—C24—C29	−75.6 (3)
C6—N3—C7—C8	57.5 (4)	C18—B1—C24—C29	47.5 (3)
N3—C7—C8—C9	56.9 (4)	C30—B1—C24—C29	164.0 (2)
C7—C8—C9—N4	46.0 (4)	C29—C24—C25—C26	−2.6 (4)
C8—C9—N4—C11	−170.0 (3)	B1—C24—C25—C26	−177.0 (3)
C8—C9—N4—C10	70.0 (4)	C24—C25—C26—C27	1.3 (5)
C24—B1—C12—C13	106.9 (3)	C25—C26—C27—C28	0.9 (5)
C18—B1—C12—C13	−15.7 (4)	C26—C27—C28—C29	−1.6 (4)
C30—B1—C12—C13	−132.5 (3)	C27—C28—C29—C24	0.2 (4)
C24—B1—C12—C17	−69.3 (3)	C25—C24—C29—C28	1.8 (4)
C18—B1—C12—C17	168.2 (3)	B1—C24—C29—C28	176.5 (3)
C30—B1—C12—C17	51.4 (4)	C12—B1—C30—C31	19.6 (4)
C17—C12—C13—C14	−1.8 (4)	C24—B1—C30—C31	136.7 (3)
B1—C12—C13—C14	−178.2 (3)	C18—B1—C30—C31	−102.3 (3)
C12—C13—C14—C15	0.5 (5)	C12—B1—C30—C35	−162.8 (3)
C13—C14—C15—C16	0.7 (5)	C24—B1—C30—C35	−45.7 (4)
C14—C15—C16—C17	−0.5 (5)	C18—B1—C30—C35	75.3 (3)
C15—C16—C17—C12	−1.0 (5)	C35—C30—C31—C32	−0.4 (4)
C13—C12—C17—C16	2.1 (5)	B1—C30—C31—C32	177.3 (3)
B1—C12—C17—C16	178.7 (3)	C30—C31—C32—C33	1.6 (5)
C12—B1—C18—C23	−47.2 (4)	C31—C32—C33—C34	−1.6 (5)
C24—B1—C18—C23	−166.0 (3)	C32—C33—C34—C35	0.5 (5)
C30—B1—C18—C23	73.4 (3)	C33—C34—C35—C30	0.7 (5)
C12—B1—C18—C19	138.4 (3)	C31—C30—C35—C34	−0.7 (4)
C24—B1—C18—C19	19.6 (4)	B1—C30—C35—C34	−178.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2C···Cg1i	0.98	2.48	3.425 (1)	162
C7—H7A···Cg2ii	0.99	2.84	3.821 (1)	170
C3—H3A···Cg2i	0.98	2.89	3.680 (1)	138
C9—H9A···Cg3iii	0.99	2.82	3.610 (1)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C30–C35, C18–C23 and C24–C29 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2C⋯Cg1i	0.98	2.48	3.425 (1)	162
C7—H7A⋯Cg2ii	0.99	2.84	3.821 (1)	170
C3—H3A⋯Cg2i	0.98	2.89	3.680 (1)	138
C9—H9A⋯Cg3iii	0.99	2.82	3.610 (1)	136

Symmetry codes: (i) ; (ii) ; (iii) .