N,N,N′,N′-Tetra­methyl­guanidinium tetra­phenyl­borate

Tiritiris, I.

doi:10.1107/S160053681204860X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3500

doi:10.1107/S160053681204860X

Open

access

N,N,N′,N′-Tetramethylguanidinium tetraphenylborate

Ioannis Tiritiris ^a ^*

^aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
^*Correspondence e-mail: Ioannis.Tiritiris@htw-aalen.de

(Received 21 November 2012; accepted 26 November 2012; online 30 November 2012)

In the title salt, C₅H₁₄N₃⁺·C₂₄H₂₀B⁻, the C—N bond lengths in the central CN₃ unit are 1.3322 (11), 1.3385 (12) and 1.3422 (12) Å, indicating partial double-bond character. The central C atom is bonded to the three N atoms in a nearly ideal trigonal-planar geometry [N—C—N angles = 119.51 (8), 119.81 (9) and 120.69 (8)°] and the positive charge is delocalized in the CN₃ plane. The bond lengths between the N atoms and the terminal methyl groups all have values close to a typical single bond [1.4597 (12)–1.4695 (13) Å]. The crystal packing is caused by electrostatic interactions between cations and anions.

Related literature

For related structures, see: Fischer & Jones (2002 ); Berg et al. (2010 ); Tiritiris et al. (2011 ); Criado et al. (2000 ); Kanters et al. (1992 ); Bujak et al. (1999 ); Wong et al. (2004 ); Pajzderska et al. (2002 ).

Experimental

Crystal data

C₅H₁₄N₃⁺·C₂₄H₂₀B⁻
M_r = 435.40
Monoclinic, P 2₁ /n
a = 10.9512 (5) Å
b = 18.1315 (9) Å
c = 12.5453 (7) Å
β = 96.594 (2)°
V = 2474.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 100 K
0.23 × 0.16 × 0.12 mm

Data collection

Bruker Kappa APEXII DUO diffractometer
52874 measured reflections
7573 independent reflections
6738 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.112
S = 1.04
7573 reflections
310 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204860X/ff2091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204860X/ff2091Isup2.hkl

checkCIF report

Comment top

Salts with the N,N,N',N'-tetramethylguanidinium ion (tmg⁺) are usually synthesized by protonation of the base N,N, N',N'-tetramethylguanidine with the appropriate acids. Until now, the crystal structures of several tmgX salts were elucidated (tmgCl: Fischer & Jones, 2002; tmgBr: Berg et al., 2010; tmgHCO₃: Tiritiris et al., 2011; tmgH₂PO₄: Criado et al., 2000; tmg⁺ pentachlorophenolate as complex with pentachlorophenol: Kanters et al., 1992; tmgSbCl₄: Bujak et al., 1999). Starting from the salt tmgCl (Fischer & Jones, 2002) by reacting with sodium tetraphenylborate, it was possible to achieve an anion exchange and to obtain the title compound. According to the structure analysis, the C1–N1 bond is 1.3385 (12) Å, C1–N2 = 1.3322 (11) Å and C1–N3 = 1.3422 (12) Å, showing partial double-bond character. The N–C1–N angles are: 120.69 (8)° (N1–C1–N2), 119.51 (8)° (N1–C1–N3) and 119.81 (9)° (N2–C1–N3), which indicates a nearly ideal trigonal-planar surrounding of the carbon centre by the nitrogen atoms (Fig. 1). The positive charge is completely delocalized on the CN₃ plane. The bonds between the N atoms and the terminal C-methyl groups, all have values close to a typical single bond [1.4597 (12)–1.4695 (13) Å]. The bond lengths and angles in the tetraphenylborate ion are in good agreement with the data from the crystal structure analysis of potassium tetraphenylborate (Wong et al., 2004) or rubidium tetraphenylborate (Pajzderska et al., 2002). Since there exist no hydrogen bonds in the title compound, crystal packing is caused by electrostatic interactions between cations and anions.

Related literature top

For related structures, see: Fischer & Jones (2002); Berg et al. (2010); Tiritiris et al. (2011); Criado et al. (2000); Kanters et al. (1992); Bujak et al. (1999); Wong et al. (2004); Pajzderska et al. (2002).

Experimental top

The title compound was obtained in an anion exchange reaction by reacting 2.0 g (13 mmol) of N,N,N',N'-tetramethylguanidinium chloride (Fischer & Jones, 2002) with 4.45 g (13 mmol) of sodium tetraphenylborate in 50 ml of acetonitrile at room temperature. After heating the mixture for 10 minutes at 353 K, the precipitated sodium chloride was filtered off. After evaporation of the solvent a colorless solid has been obtained. The title compound was recrystallized from a saturated acetonitrile solution and after several days at 273 K, colorless single crystals were formed. Yield: 5.2 g (92%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound with atom labels and 50% probability displacement ellipsoids.

N,N,N',N'-Tetramethylguanidinium tetraphenylborate top

Crystal data top

C₅H₁₄N₃⁺·C₂₄H₂₀B⁻	F(000) = 936
M_r = 435.40	D_x = 1.169 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 52874 reflections
a = 10.9512 (5) Å	θ = 2.0–30.6°
b = 18.1315 (9) Å	µ = 0.07 mm⁻¹
c = 12.5453 (7) Å	T = 100 K
β = 96.594 (2)°	Block, colourless
V = 2474.5 (2) Å³	0.23 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker Kappa APEXII DUO diffractometer	6738 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.021
Graphite monochromator	θ_max = 30.6°, θ_min = 2.0°
ϕ scans, and ω scans	h = −15→15
52874 measured reflections	k = −25→25
7573 independent reflections	l = −12→17

Refinement top

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)] = 0.041	Hydrogen site location: difference Fourier map
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0559P)² + 0.9205P] where P = (F_o² + 2F_c²)/3
7573 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₅H₁₄N₃⁺·C₂₄H₂₀B⁻	V = 2474.5 (2) Å³
M_r = 435.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9512 (5) Å	µ = 0.07 mm⁻¹
b = 18.1315 (9) Å	T = 100 K
c = 12.5453 (7) Å	0.23 × 0.16 × 0.12 mm
β = 96.594 (2)°

Data collection top

Bruker Kappa APEXII DUO diffractometer	6738 reflections with I > 2σ(I)
52874 measured reflections	R_int = 0.021
7573 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.40 e Å⁻³
7573 reflections	Δρ_min = −0.31 e Å⁻³
310 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.74190 (7)	0.06305 (5)	0.71562 (6)	0.01888 (15)
N2	0.60284 (7)	0.13924 (5)	0.78860 (6)	0.02054 (16)
N3	0.80829 (8)	0.14087 (5)	0.85684 (7)	0.02289 (17)
H30	0.8870 (16)	0.1353 (9)	0.8435 (13)	0.041 (4)*
H31	0.7911 (15)	0.1668 (9)	0.9157 (13)	0.038 (4)*
C1	0.71704 (8)	0.11437 (5)	0.78672 (7)	0.01750 (16)
C2	0.67627 (9)	0.06015 (6)	0.60739 (8)	0.02425 (19)
H2A	0.6199	0.1022	0.5968	0.036*
H2B	0.6294	0.0141	0.5983	0.036*
H2C	0.7355	0.0623	0.5546	0.036*
C3	0.85459 (8)	0.01960 (6)	0.73372 (8)	0.02234 (18)
H3A	0.9218	0.0463	0.7056	0.034*
H3B	0.8423	−0.0279	0.6969	0.034*
H3C	0.8754	0.0113	0.8109	0.034*
C4	0.57784 (10)	0.20819 (6)	0.84245 (8)	0.0281 (2)
H4A	0.5715	0.1984	0.9185	0.042*
H4B	0.5004	0.2292	0.8089	0.042*
H4C	0.6449	0.2431	0.8361	0.042*
C5	0.49544 (9)	0.09133 (6)	0.76198 (8)	0.0262 (2)
H5A	0.5230	0.0408	0.7510	0.039*
H5B	0.4476	0.1091	0.6962	0.039*
H5C	0.4441	0.0921	0.8210	0.039*
B1	0.77207 (8)	0.10576 (5)	0.22287 (7)	0.01225 (15)
C6	0.62087 (7)	0.10464 (4)	0.20365 (6)	0.01299 (14)
C7	0.56097 (8)	0.08674 (5)	0.10126 (7)	0.01578 (15)
H7A	0.6098	0.0758	0.0454	0.019*
C8	0.43355 (8)	0.08443 (5)	0.07831 (7)	0.01832 (16)
H8A	0.3973	0.0719	0.0082	0.022*
C9	0.35964 (8)	0.10055 (5)	0.15814 (8)	0.02010 (17)
H9A	0.2726	0.1000	0.1430	0.024*
C10	0.41494 (8)	0.11741 (6)	0.26041 (8)	0.02207 (18)
H10A	0.3654	0.1281	0.3159	0.026*
C11	0.54315 (8)	0.11869 (5)	0.28233 (7)	0.01841 (16)
H11A	0.5787	0.1295	0.3533	0.022*
C12	0.82722 (7)	0.13031 (4)	0.34510 (6)	0.01287 (14)
C13	0.78885 (8)	0.19702 (5)	0.38812 (7)	0.01620 (15)
H13A	0.7268	0.2250	0.3471	0.019*
C14	0.83773 (8)	0.22387 (5)	0.48811 (7)	0.01935 (17)
H14A	0.8077	0.2687	0.5144	0.023*
C15	0.93051 (9)	0.18509 (6)	0.54945 (7)	0.02074 (18)
H15A	0.9638	0.2028	0.6179	0.025*
C16	0.97343 (8)	0.12013 (5)	0.50873 (7)	0.01963 (17)
H16A	1.0381	0.0937	0.5488	0.024*
C17	0.92193 (8)	0.09334 (5)	0.40884 (7)	0.01579 (15)
H17A	0.9522	0.0484	0.3832	0.019*
C18	0.81527 (7)	0.02273 (4)	0.19171 (6)	0.01238 (14)
C19	0.79975 (7)	−0.03773 (5)	0.25931 (6)	0.01439 (15)
H19	0.7684	−0.0289	0.3257	0.017*
C20	0.82836 (8)	−0.10987 (5)	0.23308 (7)	0.01630 (16)
H20A	0.8165	−0.1490	0.2812	0.020*
C21	0.87440 (8)	−0.12473 (5)	0.13634 (7)	0.01601 (15)
H21	0.8955	−0.1737	0.1184	0.019*
C22	0.88900 (8)	−0.06665 (5)	0.06645 (7)	0.01521 (15)
H22A	0.9192	−0.0759	−0.0003	0.018*
C23	0.85949 (7)	0.00525 (5)	0.09407 (6)	0.01382 (15)
H23A	0.8698	0.0439	0.0448	0.017*
C24	0.82661 (8)	0.16882 (4)	0.14711 (6)	0.01348 (14)
C25	0.95325 (8)	0.17168 (5)	0.13683 (7)	0.01668 (16)
H25A	1.0053	0.1345	0.1707	0.020*
C26	1.00537 (9)	0.22663 (5)	0.07917 (7)	0.02039 (17)
H26A	1.0912	0.2262	0.0737	0.024*
C27	0.93187 (10)	0.28230 (5)	0.02953 (7)	0.02249 (18)
H27A	0.9668	0.3197	−0.0106	0.027*
C28	0.80688 (9)	0.28248 (5)	0.03943 (7)	0.02106 (18)
H28A	0.7560	0.3207	0.0071	0.025*
C29	0.75587 (8)	0.22642 (5)	0.09701 (7)	0.01653 (16)
H29A	0.6701	0.2274	0.1024	0.020*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0149 (3)	0.0227 (4)	0.0191 (3)	0.0019 (3)	0.0022 (3)	−0.0004 (3)
N2	0.0162 (3)	0.0255 (4)	0.0199 (3)	0.0044 (3)	0.0020 (3)	0.0012 (3)
N3	0.0170 (4)	0.0286 (4)	0.0225 (4)	0.0026 (3)	−0.0004 (3)	−0.0053 (3)
C1	0.0158 (4)	0.0202 (4)	0.0166 (4)	0.0012 (3)	0.0024 (3)	0.0027 (3)
C2	0.0218 (4)	0.0321 (5)	0.0184 (4)	−0.0026 (4)	0.0003 (3)	−0.0018 (3)
C3	0.0159 (4)	0.0233 (4)	0.0280 (4)	0.0023 (3)	0.0035 (3)	−0.0016 (3)
C4	0.0294 (5)	0.0328 (5)	0.0222 (4)	0.0154 (4)	0.0027 (4)	−0.0002 (4)
C5	0.0144 (4)	0.0379 (6)	0.0262 (5)	−0.0005 (4)	0.0025 (3)	0.0076 (4)
B1	0.0119 (4)	0.0130 (4)	0.0121 (4)	0.0004 (3)	0.0021 (3)	−0.0005 (3)
C6	0.0131 (3)	0.0122 (3)	0.0138 (3)	0.0006 (3)	0.0019 (3)	0.0006 (3)
C7	0.0157 (4)	0.0173 (4)	0.0143 (3)	0.0000 (3)	0.0014 (3)	−0.0001 (3)
C8	0.0166 (4)	0.0200 (4)	0.0174 (4)	−0.0012 (3)	−0.0020 (3)	0.0019 (3)
C9	0.0126 (4)	0.0237 (4)	0.0235 (4)	−0.0002 (3)	0.0001 (3)	0.0020 (3)
C10	0.0140 (4)	0.0312 (5)	0.0217 (4)	0.0004 (3)	0.0048 (3)	−0.0035 (3)
C11	0.0142 (4)	0.0250 (4)	0.0162 (4)	−0.0002 (3)	0.0027 (3)	−0.0035 (3)
C12	0.0122 (3)	0.0137 (3)	0.0131 (3)	−0.0007 (3)	0.0030 (3)	−0.0006 (3)
C13	0.0160 (4)	0.0152 (4)	0.0173 (4)	0.0001 (3)	0.0020 (3)	−0.0024 (3)
C14	0.0192 (4)	0.0196 (4)	0.0198 (4)	−0.0037 (3)	0.0047 (3)	−0.0067 (3)
C15	0.0195 (4)	0.0267 (4)	0.0159 (4)	−0.0072 (3)	0.0014 (3)	−0.0047 (3)
C16	0.0160 (4)	0.0254 (4)	0.0167 (4)	−0.0015 (3)	−0.0017 (3)	0.0006 (3)
C17	0.0143 (3)	0.0175 (4)	0.0155 (3)	0.0006 (3)	0.0014 (3)	−0.0005 (3)
C18	0.0103 (3)	0.0136 (3)	0.0131 (3)	0.0000 (3)	0.0011 (2)	−0.0009 (3)
C19	0.0138 (3)	0.0151 (4)	0.0146 (3)	−0.0008 (3)	0.0028 (3)	−0.0001 (3)
C20	0.0160 (4)	0.0135 (4)	0.0194 (4)	−0.0018 (3)	0.0022 (3)	0.0014 (3)
C21	0.0137 (3)	0.0132 (3)	0.0210 (4)	−0.0008 (3)	0.0015 (3)	−0.0031 (3)
C22	0.0139 (3)	0.0167 (4)	0.0154 (3)	−0.0006 (3)	0.0029 (3)	−0.0036 (3)
C23	0.0136 (3)	0.0143 (3)	0.0136 (3)	−0.0003 (3)	0.0018 (3)	−0.0003 (3)
C24	0.0157 (3)	0.0128 (3)	0.0122 (3)	−0.0005 (3)	0.0030 (3)	−0.0022 (3)
C25	0.0158 (4)	0.0174 (4)	0.0173 (4)	−0.0017 (3)	0.0039 (3)	−0.0026 (3)
C26	0.0208 (4)	0.0228 (4)	0.0188 (4)	−0.0074 (3)	0.0077 (3)	−0.0048 (3)
C27	0.0317 (5)	0.0199 (4)	0.0170 (4)	−0.0089 (4)	0.0076 (3)	−0.0009 (3)
C28	0.0302 (5)	0.0153 (4)	0.0180 (4)	−0.0007 (3)	0.0038 (3)	0.0022 (3)
C29	0.0196 (4)	0.0147 (4)	0.0157 (3)	0.0007 (3)	0.0038 (3)	0.0001 (3)

Geometric parameters (Å, º) top

N1—C1	1.3385 (12)	C11—H11A	0.9500
N1—C3	1.4597 (12)	C12—C17	1.4050 (11)
N1—C2	1.4624 (12)	C12—C13	1.4081 (11)
N2—C1	1.3322 (11)	C13—C14	1.3939 (12)
N2—C4	1.4617 (13)	C13—H13A	0.9500
N2—C5	1.4695 (13)	C14—C15	1.3927 (13)
N3—C1	1.3422 (12)	C14—H14A	0.9500
N3—H30	0.903 (17)	C15—C16	1.3872 (14)
N3—H31	0.914 (16)	C15—H15A	0.9500
C2—H2A	0.9800	C16—C17	1.4008 (12)
C2—H2B	0.9800	C16—H16A	0.9500
C2—H2C	0.9800	C17—H17A	0.9500
C3—H3A	0.9800	C18—C23	1.4042 (11)
C3—H3B	0.9800	C18—C19	1.4083 (11)
C3—H3C	0.9800	C19—C20	1.3931 (12)
C4—H4A	0.9800	C19—H19	0.9500
C4—H4B	0.9800	C20—C21	1.3930 (12)
C4—H4C	0.9800	C20—H20A	0.9500
C5—H5A	0.9800	C21—C22	1.3911 (12)
C5—H5B	0.9800	C21—H21	0.9500
C5—H5C	0.9800	C22—C23	1.3964 (11)
B1—C18	1.6388 (12)	C22—H22A	0.9500
B1—C24	1.6423 (12)	C23—H23A	0.9500
B1—C12	1.6436 (12)	C24—C29	1.4051 (12)
B1—C6	1.6458 (12)	C24—C25	1.4085 (11)
C6—C11	1.3988 (11)	C25—C26	1.3916 (12)
C6—C7	1.4114 (11)	C25—H25A	0.9500
C7—C8	1.3926 (12)	C26—C27	1.3927 (14)
C7—H7A	0.9500	C26—H26A	0.9500
C8—C9	1.3891 (13)	C27—C28	1.3886 (14)
C8—H8A	0.9500	C27—H27A	0.9500
C9—C10	1.3885 (13)	C28—C29	1.3999 (12)
C9—H9A	0.9500	C28—H28A	0.9500
C10—C11	1.3996 (12)	C29—H29A	0.9500
C10—H10A	0.9500

C1—N1—C3	120.30 (8)	C6—C11—C10	122.44 (8)
C1—N1—C2	121.86 (8)	C6—C11—H11A	118.8
C3—N1—C2	116.21 (8)	C10—C11—H11A	118.8
C1—N2—C4	121.58 (8)	C17—C12—C13	115.15 (7)
C1—N2—C5	121.62 (9)	C17—C12—B1	124.75 (7)
C4—N2—C5	115.04 (8)	C13—C12—B1	119.76 (7)
C1—N3—H30	119.6 (10)	C14—C13—C12	122.98 (8)
C1—N3—H31	120.5 (10)	C14—C13—H13A	118.5
H30—N3—H31	119.9 (14)	C12—C13—H13A	118.5
N2—C1—N1	120.69 (8)	C15—C14—C13	120.08 (8)
N2—C1—N3	119.81 (9)	C15—C14—H14A	120.0
N1—C1—N3	119.51 (8)	C13—C14—H14A	120.0
N1—C2—H2A	109.5	C16—C15—C14	118.80 (8)
N1—C2—H2B	109.5	C16—C15—H15A	120.6
H2A—C2—H2B	109.5	C14—C15—H15A	120.6
N1—C2—H2C	109.5	C15—C16—C17	120.34 (8)
H2A—C2—H2C	109.5	C15—C16—H16A	119.8
H2B—C2—H2C	109.5	C17—C16—H16A	119.8
N1—C3—H3A	109.5	C16—C17—C12	122.61 (8)
N1—C3—H3B	109.5	C16—C17—H17A	118.7
H3A—C3—H3B	109.5	C12—C17—H17A	118.7
N1—C3—H3C	109.5	C23—C18—C19	115.29 (7)
H3A—C3—H3C	109.5	C23—C18—B1	123.60 (7)
H3B—C3—H3C	109.5	C19—C18—B1	120.89 (7)
N2—C4—H4A	109.5	C20—C19—C18	122.86 (8)
N2—C4—H4B	109.5	C20—C19—H19	118.6
H4A—C4—H4B	109.5	C18—C19—H19	118.6
N2—C4—H4C	109.5	C21—C20—C19	120.08 (8)
H4A—C4—H4C	109.5	C21—C20—H20A	120.0
H4B—C4—H4C	109.5	C19—C20—H20A	120.0
N2—C5—H5A	109.5	C22—C21—C20	118.81 (8)
N2—C5—H5B	109.5	C22—C21—H21	120.6
H5A—C5—H5B	109.5	C20—C21—H21	120.6
N2—C5—H5C	109.5	C21—C22—C23	120.25 (8)
H5A—C5—H5C	109.5	C21—C22—H22A	119.9
H5B—C5—H5C	109.5	C23—C22—H22A	119.9
C18—B1—C24	111.55 (6)	C22—C23—C18	122.68 (8)
C18—B1—C12	112.71 (6)	C22—C23—H23A	118.7
C24—B1—C12	103.43 (6)	C18—C23—H23A	118.7
C18—B1—C6	105.47 (6)	C29—C24—C25	115.45 (8)
C24—B1—C6	110.52 (6)	C29—C24—B1	123.91 (7)
C12—B1—C6	113.31 (6)	C25—C24—B1	120.40 (7)
C11—C6—C7	115.29 (7)	C26—C25—C24	122.75 (8)
C11—C6—B1	125.30 (7)	C26—C25—H25A	118.6
C7—C6—B1	119.40 (7)	C24—C25—H25A	118.6
C8—C7—C6	123.03 (8)	C25—C26—C27	120.06 (9)
C8—C7—H7A	118.5	C25—C26—H26A	120.0
C6—C7—H7A	118.5	C27—C26—H26A	120.0
C9—C8—C7	119.84 (8)	C28—C27—C26	119.13 (8)
C9—C8—H8A	120.1	C28—C27—H27A	120.4
C7—C8—H8A	120.1	C26—C27—H27A	120.4
C10—C9—C8	118.95 (8)	C27—C28—C29	120.02 (9)
C10—C9—H9A	120.5	C27—C28—H28A	120.0
C8—C9—H9A	120.5	C29—C28—H28A	120.0
C9—C10—C11	120.43 (8)	C28—C29—C24	122.58 (8)
C9—C10—H10A	119.8	C28—C29—H29A	118.7
C11—C10—H10A	119.8	C24—C29—H29A	118.7

C4—N2—C1—N1	−162.47 (9)	C14—C15—C16—C17	−1.56 (14)
C5—N2—C1—N1	33.40 (13)	C15—C16—C17—C12	0.81 (14)
C4—N2—C1—N3	17.62 (13)	C13—C12—C17—C16	0.93 (12)
C5—N2—C1—N3	−146.51 (9)	B1—C12—C17—C16	174.07 (8)
C3—N1—C1—N2	−160.77 (9)	C24—B1—C18—C23	−18.25 (10)
C2—N1—C1—N2	34.35 (13)	C12—B1—C18—C23	−134.10 (8)
C3—N1—C1—N3	19.15 (13)	C6—B1—C18—C23	101.77 (8)
C2—N1—C1—N3	−145.74 (9)	C24—B1—C18—C19	167.38 (7)
C18—B1—C6—C11	120.33 (9)	C12—B1—C18—C19	51.53 (10)
C24—B1—C6—C11	−118.97 (9)	C6—B1—C18—C19	−72.59 (9)
C12—B1—C6—C11	−3.41 (11)	C23—C18—C19—C20	1.29 (12)
C18—B1—C6—C7	−58.20 (9)	B1—C18—C19—C20	176.11 (7)
C24—B1—C6—C7	62.51 (9)	C18—C19—C20—C21	−0.06 (13)
C12—B1—C6—C7	178.06 (7)	C19—C20—C21—C22	−1.08 (12)
C11—C6—C7—C8	1.24 (13)	C20—C21—C22—C23	0.91 (12)
B1—C6—C7—C8	179.91 (8)	C21—C22—C23—C18	0.40 (12)
C6—C7—C8—C9	0.29 (14)	C19—C18—C23—C22	−1.47 (12)
C7—C8—C9—C10	−1.19 (14)	B1—C18—C23—C22	−176.12 (7)
C8—C9—C10—C11	0.50 (15)	C18—B1—C24—C29	133.43 (8)
C7—C6—C11—C10	−1.94 (13)	C12—B1—C24—C29	−105.16 (8)
B1—C6—C11—C10	179.48 (9)	C6—B1—C24—C29	16.43 (11)
C9—C10—C11—C6	1.14 (15)	C18—B1—C24—C25	−52.52 (10)
C18—B1—C12—C17	13.50 (11)	C12—B1—C24—C25	68.88 (9)
C24—B1—C12—C17	−107.12 (9)	C6—B1—C24—C25	−169.53 (7)
C6—B1—C12—C17	133.19 (8)	C29—C24—C25—C26	−1.38 (12)
C18—B1—C12—C13	−173.65 (7)	B1—C24—C25—C26	−175.91 (8)
C24—B1—C12—C13	65.73 (9)	C24—C25—C26—C27	0.66 (13)
C6—B1—C12—C13	−53.96 (10)	C25—C26—C27—C28	0.67 (13)
C17—C12—C13—C14	−1.98 (12)	C26—C27—C28—C29	−1.20 (14)
B1—C12—C13—C14	−175.49 (8)	C27—C28—C29—C24	0.42 (14)
C12—C13—C14—C15	1.30 (14)	C25—C24—C29—C28	0.84 (12)
C13—C14—C15—C16	0.55 (14)	B1—C24—C29—C28	175.15 (8)

Experimental details

Crystal data
Chemical formula	C₅H₁₄N₃⁺·C₂₄H₂₀B⁻
M_r	435.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.9512 (5), 18.1315 (9), 12.5453 (7)
β (°)	96.594 (2)
V (Å³)	2474.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.23 × 0.16 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII DUO diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	52874, 7573, 6738
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.112, 1.04
No. of reflections	7573
No. of parameters	310
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.31

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2005).

Acknowledgements

The author thanks Dr W. Frey (Institut für Organische Chemie, Universität Stuttgart) for the data collection.

References

Berg, R. W., Riisager, A., Van Buu, O. N., Kristensen, S. B., Fehrmann, R., Harris, P. & Brunetti, A. C. (2010). J. Phys. Chem. A, 114, 13175–13181. Web of Science CSD CrossRef CAS PubMed Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bujak, M., Osadczuk, P. & Zaleski, J. (1999). Acta Cryst. C55, 1443–1447. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Criado, A., Diánez, M. J., Pérez-Garrido, S., Fernandes, I. M. L., Belsley, M. & de Matos Gomes, E. (2000). Acta Cryst. C56, 888–889. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Fischer, A. K. & Jones, P. G. (2002). Acta Cryst. E58, o218–o219. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kanters, J. A., ter Horst, E. H. & Grech, E. (1992). Acta Cryst. C48, 1345–1347. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Pajzderska, A., Maluszyńska, H. & Wasicki, J. (2002). Z. Naturforsch. Teil A, 57, 847–853. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tiritiris, I., Mezger, J., Stoyanov, E. V. & Kantlehner, W. (2011). Z. Naturforsch. Teil B, 66, 407–418. CrossRef CAS Google Scholar
Wong, A., Whitehead, R. D., Gan, Z. & Wu, G. (2004). J. Phys. Chem. A, 108, 10551–10559. Web of Science CrossRef CAS Google Scholar