Tri-benzyl-ammonium chloride.

Single crystals of the title salt, C21H21NH(+)·Cl(-), were isolated as a side product from the reaction involving [(C6H5CH2)3NH]2[HPO4] and Sn(CH3)3Cl in ethanol. Both the cation and the anion are situated on a threefold rotation axis. The central N atom in the cation has a slightly distorted tetra-hedral environment, with angles ranging from 107.7 to 111.16 (10)°. In the crystal, the tri-benzyl-ammonium cations and chloride anions are linked through N-H⋯Cl and C-H⋯Cl hydrogen bonds, leading to the formation of infinite chains along [001]. The crystal studied was a merohedral twin.

Related literature

For related crystal structures containing the tri­benzyl­ammonium cation, see: Kozhomuratova et al. (2007 ▶); Jarvinen et al. (1988 ▶); Guo et al. (2010 ▶); Zeng et al. (1994 ▶); Faza­eli et al. (2010 ▶); Guan et al. (2013 ▶); Yousefi et al. (2007 ▶); Gueye et al. (2012 ▶); Traore et al. (2013 ▶). For details of the treatment of intensity data from a twinned crystal, see: Spek (2009 ▶).

Experimental

Crystal data

C21H22N+·Cl−

M = 323.85

Trigonal,

a = 15.3833 (8) Å

c = 6.7051 (3) Å

V = 1374.15 (18) Å3

Z = 3

Mo Kα radiation

μ = 0.21 mm−1

T = 115 K

0.47 × 0.27 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.923, T max = 0.963

1884 measured reflections

1047 independent reflections

1045 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.052

S = 1.10

1047 reflections

71 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.11 e Å−3

Absolute structure: Flack parameter determined using 348 quotients [(I +)−(I −)]/[(I +)+(I −)] (Parsons et al., 2012 ▶)

Absolute structure parameter: 0.01 (4)

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814009246/wm5019sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009246/wm5019Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009246/wm5019Isup3.cml

CCDC reference: 999186

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H22N+·Cl−	Dx = 1.174 Mg m−3
Mr = 323.85	Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3	Cell parameters from 2745 reflections
Hall symbol: R 3	θ = 1.0–27.5°
a = 15.3833 (8) Å	µ = 0.21 mm−1
c = 6.7051 (3) Å	T = 115 K
V = 1374.15 (18) Å3	Prism, colourless
Z = 3	0.47 × 0.27 × 0.12 mm
F(000) = 516

Nonius KappaCCD diffractometer	1047 independent reflections
Radiation source: X-ray tube, Siemens KFF Mo 2K-180	1045 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 512 x 512 pixels mm-1	θmax = 27.5°, θmin = 3.4°
φ and ω scans	h = −18→17
Absorption correction: multi-scan (Blessing, 1995)	k = −19→10
Tmin = 0.923, Tmax = 0.963	l = −8→6
1884 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.021	w = 1/[σ2(Fo2) + 0.8302P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.052	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.12 e Å−3
1047 reflections	Δρmin = −0.11 e Å−3
71 parameters	Absolute structure: Flack parameter determined using 348 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2012)
1 restraint	Absolute structure parameter: 0.01 (4)
Primary atom site location: iterative

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. Refined as a 2-component twin.

	x	y	z	Uiso*/Ueq
Cl	0.6667	0.3333	0.80013 (9)	0.02215 (17)
N	0.6667	0.3333	0.2481 (3)	0.0146 (5)
H	0.6667	0.3333	0.0990	0.018*
C1	0.56631 (12)	0.31837 (13)	0.3169 (3)	0.0168 (3)
H1A	0.5122	0.2574	0.2520	0.020*
H1B	0.5604	0.3064	0.4626	0.020*
C2	0.55016 (13)	0.40504 (12)	0.2725 (3)	0.0176 (4)
C3	0.51543 (14)	0.41462 (15)	0.0861 (3)	0.0231 (4)
H3	0.5043	0.3676	−0.0165	0.028*
C4	0.49715 (17)	0.49308 (17)	0.0510 (3)	0.0313 (5)
H4	0.4731	0.4991	−0.0757	0.038*
C5	0.51373 (16)	0.56246 (15)	0.1988 (4)	0.0332 (5)
H5	0.5011	0.6159	0.1738	0.040*
C6	0.54881 (15)	0.55355 (16)	0.3832 (4)	0.0313 (5)
H6	0.5613	0.6016	0.4844	0.038*
C7	0.56583 (14)	0.47482 (14)	0.4207 (3)	0.0234 (4)
H7	0.5884	0.4683	0.5487	0.028*

	U11	U22	U33	U12	U13	U23
Cl	0.0273 (2)	0.0273 (2)	0.0118 (3)	0.01366 (12)	0.000	0.000
N	0.0156 (6)	0.0156 (6)	0.0128 (13)	0.0078 (3)	0.000	0.000
C1	0.0151 (7)	0.0189 (8)	0.0162 (8)	0.0084 (7)	0.0009 (7)	0.0013 (7)
C2	0.0139 (8)	0.0187 (8)	0.0202 (9)	0.0080 (7)	0.0013 (6)	−0.0002 (7)
C3	0.0240 (9)	0.0268 (9)	0.0220 (10)	0.0155 (8)	−0.0003 (7)	0.0000 (7)
C4	0.0317 (11)	0.0362 (11)	0.0349 (10)	0.0237 (9)	0.0028 (9)	0.0099 (10)
C5	0.0268 (10)	0.0240 (10)	0.0558 (15)	0.0178 (8)	0.0105 (10)	0.0066 (10)
C6	0.0227 (9)	0.0242 (9)	0.0478 (14)	0.0123 (8)	0.0087 (9)	−0.0072 (9)
C7	0.0186 (9)	0.0258 (10)	0.0254 (10)	0.0108 (8)	0.0014 (7)	−0.0053 (8)

N—H	1.0000	C3—H3	0.9500
N—C1i	1.5145 (17)	C3—C4	1.389 (3)
N—C1ii	1.5145 (17)	C4—H4	0.9500
N—C1	1.5145 (17)	C4—C5	1.384 (3)
C1—H1A	0.9900	C5—H5	0.9500
C1—H1B	0.9900	C5—C6	1.383 (3)
C1—C2	1.503 (2)	C6—H6	0.9500
C2—C3	1.396 (3)	C6—C7	1.384 (3)
C2—C7	1.392 (2)	C7—H7	0.9500
C1ii—N—H	107.7	C2—C3—H3	120.1
C1i—N—H	107.7	C4—C3—C2	119.86 (19)
C1—N—H	107.7	C4—C3—H3	120.1
C1ii—N—C1i	111.16 (10)	C3—C4—H4	119.7
C1i—N—C1	111.16 (10)	C5—C4—C3	120.6 (2)
C1ii—N—C1	111.16 (10)	C5—C4—H4	119.7
N—C1—H1A	108.7	C4—C5—H5	120.2
N—C1—H1B	108.7	C6—C5—C4	119.63 (19)
H1A—C1—H1B	107.6	C6—C5—H5	120.2
C2—C1—N	114.39 (13)	C5—C6—H6	119.9
C2—C1—H1A	108.7	C5—C6—C7	120.2 (2)
C2—C1—H1B	108.7	C7—C6—H6	119.9
C3—C2—C1	120.83 (16)	C2—C7—H7	119.7
C7—C2—C1	120.07 (16)	C6—C7—C2	120.62 (19)
C7—C2—C3	119.04 (17)	C6—C7—H7	119.7
N—C1—C2—C3	83.7 (2)	C2—C3—C4—C5	0.5 (3)
N—C1—C2—C7	−99.0 (2)	C3—C2—C7—C6	−1.0 (3)
C1ii—N—C1—C2	174.09 (11)	C3—C4—C5—C6	0.0 (3)
C1i—N—C1—C2	49.7 (2)	C4—C5—C6—C7	−1.0 (3)
C1—C2—C3—C4	177.39 (18)	C5—C6—C7—C2	1.5 (3)
C1—C2—C7—C6	−178.38 (17)	C7—C2—C3—C4	0.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H···Cliii	1.00	2.00	3.004 (2)	180
C1—H1B···Cl	0.99	2.70	3.5470 (18)	144
C3—H3···Cliii	0.95	3.06	3.683 (2)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H⋯Cli	1.00	2.00	3.004 (2)	180
C1—H1B⋯Cl	0.99	2.70	3.5470 (18)	144
C3—H3⋯Cli	0.95	3.06	3.683 (2)	125

Symmetry code: (i) .