(Anthracen-9-ylmeth­yl)benzyl­ammonium chloride

Han, J.-R.; Wang, W.; Zhen, X.-L.; Tian, X.; Liu, S.-X.

doi:10.1107/S1600536811016837

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1482

doi:10.1107/S1600536811016837

Open

access

(Anthracen-9-ylmethyl)benzylammonium chloride

Jian-Rong Han,^a ^* Wei Wang,^a Xiao-Li Zhen,^a Xia Tian ^a and Shou-Xin Liu ^b ‡

^aCollege of Sciences, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China, and ^bCollege of Chemical & Pharmaceutical Engineering, Hebei University of Science & Technology, Shijiazhuang 050018, People's Republic of China
^*Correspondence e-mail: han_jianrong@126com

(Received 11 April 2011; accepted 4 May 2011; online 20 May 2011)

In the title compound, C₂₂H₂₀N⁺·Cl⁻, the anthracene system makes a dihedral angle of 72.65 (4)° with the benzene ring. The C—N—C—C torsion angles in the chain connecting the benzene ring and anthracene system are 52.24 (15) and −170.73 (11)°. The crystal structure is stabilized by intermolecular N—H⋯Cl and C—H⋯Cl hydrogen bonds, which link the molecules into tetramers about inversion centers.

Related literature

For the synthesis and structures of related compounds, see: Ashton et al. (1997 ). For formation of rotaxanes from sec-ammonium salts and crown ethers, see: Nakazono et al. (2008 ).

Experimental

Crystal data

C₂₂H₂₀N⁺·Cl⁻
M_r = 333.84
Triclinic, $[P \overline 1]$
a = 6.7457 (13) Å
b = 10.761 (2) Å
c = 13.033 (3) Å
α = 94.45 (3)°
β = 104.84 (3)°
γ = 104.48 (3)°
V = 875.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 113 K
0.28 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.941, T_max = 0.957
5882 measured reflections
3048 independent reflections
2342 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.088
S = 1.04
3048 reflections
226 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1ⁱ	0.92 (1)	2.26 (1)	3.0963 (13)	152 (1)
N1—H1B⋯Cl1	0.92 (1)	2.17 (1)	3.0781 (16)	170 (1)
C16—H16A⋯Cl1ⁱⁱ	0.97	2.60	3.4824 (16)	151
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016837/pv2409sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811016837/pv2409Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811016837/pv2409Isup3.cml

checkCIF report

Comment top

Sec-ammonium salts and crown ethers combine well to yield a stable pseudorotaxanes as a precursor of rotaxanes (Nakazono et al., 2008). (9-Anthracenyl) benzylammonium hexafluorophosphate and aromatic crown ethers give hydrogen-bonded complexes pseudorotaxane-like geometries (Ashton et al., 1997). In this paper we report the synthesis and crystal strucure of (9-anthracenyl) benzyl ammonium chloride.

In the title compound (Fig. 1), anthracene ring makes a dihedral angle of 72.65 (4)° with benzene ring. The torsion angles in the chain connecting the benzene and the anthracene rings, (C15/N1—C16/C17 and (C16/N1—C15/C14) are 52.24 (15) ° and -170.73 (11)°, respectively. In the crystal structure, the crystal packing is stabilized by intermolecular N1—H1A···Cl1 and C16—H16A···Cl1 hydrogen bonds which link the molecules into tetramers about inversion centers (Table 1 and Fig. 2).

Related literature top

For synthesis and structures of related compounds, see: Ashton et al. (1997). For formation of rotaxanes from sec-ammonium salts and crown ethers, see: Nakazono et al. (2008).

Experimental top

A mixture of 9-anthracenealdehyde (6.18 g, 30 mmol) and benzylamine (3.86 g, 36 mmol) and molecular Sieve in toluene (200 mL) was heated under reflux with stirring in a water divider for 10 h. After the reaction mixture had cooled down to room temperature, the solvent was removed in vacuo to give the imine. The solid was dissolved in hot MeOH (150 mL), followed by drop-wise addition of NaBH₄ (5.70 g, 150 mmol) and heating under reflux with stirring for 8 h. The reaction mixture was then allowed to cool down to room temperature, and concentrated HCl was added (pH<2). After evaporation of the solvent, the residue was suspended in H₂O (70 mL) and extracted with CH₂Cl₂ (4 × 50 mL). The combined extracts were washed with 5% aqueous NaHCO₃ (2× 70 mL) and H₂O (70 mL) and then dried (MgSO₄). Removal of the solvent in vacuo afforded the (9-anthracenyl)benzyl amine which was treated according to literature (Ashton et al., 1997) to prepare the title compound. Pale yellow single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an methnol solution.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, with 50% probablity ellipsoids.
	Fig. 2. Unit cell packing of the title complex, showing hydrogen bonded tetramers.

(Anthracen-9-ylmethyl)benzylammonium chloride top

Crystal data top

C₂₂H₂₀N⁺·Cl⁻	Z = 2
M_r = 333.84	F(000) = 352
Triclinic, P1	D_x = 1.267 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7457 (13) Å	Cell parameters from 2756 reflections
b = 10.761 (2) Å	θ = 2.4–27.9°
c = 13.033 (3) Å	µ = 0.22 mm⁻¹
α = 94.45 (3)°	T = 113 K
β = 104.84 (3)°	Block, yellow
γ = 104.48 (3)°	0.28 × 0.24 × 0.20 mm
V = 875.3 (3) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3048 independent reflections
Radiation source: rotating anode	2342 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.027
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.0°, θ_min = 2.4°
ω and ϕ scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→10
T_min = 0.941, T_max = 0.957	l = −15→15
5882 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.031	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0502P)²] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.002
3048 reflections	Δρ_max = 0.20 e Å⁻³
226 parameters	Δρ_min = −0.21 e Å⁻³
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.152 (9)

Crystal data top

C₂₂H₂₀N⁺·Cl⁻	γ = 104.48 (3)°
M_r = 333.84	V = 875.3 (3) Å³
Triclinic, P1	Z = 2
a = 6.7457 (13) Å	Mo Kα radiation
b = 10.761 (2) Å	µ = 0.22 mm⁻¹
c = 13.033 (3) Å	T = 113 K
α = 94.45 (3)°	0.28 × 0.24 × 0.20 mm
β = 104.84 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	3048 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	2342 reflections with I > 2σ(I)
T_min = 0.941, T_max = 0.957	R_int = 0.027
5882 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	3 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
3048 reflections	Δρ_min = −0.21 e Å⁻³
226 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
Cl1	0.17351 (5)	0.42040 (4)	0.40032 (3)	0.02288 (15)
N1	0.38238 (18)	0.52936 (11)	0.64009 (9)	0.0139 (3)
C1	0.1631 (2)	0.21072 (14)	0.67206 (11)	0.0184 (3)
C2	−0.0472 (2)	0.21057 (16)	0.61273 (12)	0.0242 (4)
H2	−0.0774	0.2890	0.6018	0.029*
C3	−0.2034 (3)	0.09727 (16)	0.57217 (13)	0.0305 (4)
H3	−0.3391	0.0995	0.5340	0.037*
C4	−0.1629 (3)	−0.02440 (17)	0.58713 (13)	0.0341 (4)
H4	−0.2721	−0.1009	0.5597	0.041*
C5	0.0344 (3)	−0.02903 (16)	0.64127 (12)	0.0305 (4)
H5	0.0595	−0.1091	0.6505	0.037*
C6	0.2045 (3)	0.08678 (15)	0.68441 (12)	0.0227 (4)
C7	0.4101 (3)	0.08322 (16)	0.73768 (12)	0.0262 (4)
H7	0.4365	0.0029	0.7438	0.031*
C8	0.5764 (2)	0.19449 (15)	0.78173 (11)	0.0223 (4)
C9	0.7883 (3)	0.18991 (18)	0.83401 (12)	0.0299 (4)
H9	0.8163	0.1098	0.8382	0.036*
C10	0.9485 (3)	0.29980 (18)	0.87736 (12)	0.0315 (4)
H10	1.0853	0.2948	0.9103	0.038*
C11	0.9084 (2)	0.42185 (17)	0.87262 (11)	0.0273 (4)
H11	1.0193	0.4969	0.9030	0.033*
C12	0.7099 (2)	0.43137 (16)	0.82427 (11)	0.0221 (4)
H12	0.6871	0.5130	0.8231	0.026*
C13	0.5357 (2)	0.31906 (15)	0.77525 (11)	0.0188 (3)
C14	0.3287 (2)	0.32511 (14)	0.72005 (11)	0.0170 (3)
C15	0.2884 (2)	0.45631 (14)	0.71774 (11)	0.0167 (3)
H15A	0.1356	0.4454	0.6977	0.020*
H15B	0.3499	0.5065	0.7891	0.020*
C16	0.3787 (2)	0.66897 (14)	0.64641 (11)	0.0159 (3)
H16A	0.2322	0.6725	0.6209	0.019*
H16B	0.4571	0.7116	0.6000	0.019*
C17	0.4765 (2)	0.74042 (14)	0.75999 (11)	0.0160 (3)
C18	0.3455 (2)	0.75556 (14)	0.82421 (12)	0.0214 (4)
H18	0.1978	0.7247	0.7963	0.026*
C19	0.4352 (3)	0.81680 (15)	0.93001 (12)	0.0277 (4)
H19	0.3472	0.8261	0.9729	0.033*
C20	0.6531 (3)	0.86365 (16)	0.97157 (13)	0.0300 (4)
H20	0.7122	0.9046	1.0424	0.036*
C21	0.7851 (3)	0.84988 (15)	0.90801 (12)	0.0254 (4)
H21	0.9326	0.8817	0.9360	0.030*
C22	0.6962 (2)	0.78841 (14)	0.80265 (11)	0.0194 (3)
H22	0.7848	0.7793	0.7601	0.023*
H1A	0.5219 (14)	0.5298 (15)	0.6487 (11)	0.027 (4)*
H1B	0.3065 (17)	0.4908 (14)	0.5707 (8)	0.018 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0145 (2)	0.0350 (3)	0.0170 (2)	0.00489 (17)	0.00408 (14)	−0.00094 (16)
N1	0.0128 (6)	0.0149 (7)	0.0127 (6)	0.0023 (5)	0.0032 (5)	0.0016 (5)
C1	0.0249 (8)	0.0171 (8)	0.0153 (7)	0.0035 (7)	0.0110 (6)	0.0039 (6)
C2	0.0265 (9)	0.0237 (9)	0.0219 (8)	0.0031 (7)	0.0102 (7)	0.0024 (7)
C3	0.0249 (9)	0.0339 (11)	0.0270 (9)	−0.0032 (8)	0.0090 (7)	0.0034 (8)
C4	0.0413 (11)	0.0230 (9)	0.0302 (9)	−0.0108 (8)	0.0172 (8)	0.0002 (8)
C5	0.0479 (11)	0.0167 (9)	0.0285 (9)	0.0017 (8)	0.0208 (8)	0.0045 (7)
C6	0.0365 (10)	0.0161 (8)	0.0194 (8)	0.0044 (7)	0.0171 (7)	0.0039 (7)
C7	0.0434 (10)	0.0212 (9)	0.0259 (8)	0.0176 (8)	0.0201 (8)	0.0109 (7)
C8	0.0321 (9)	0.0257 (9)	0.0171 (7)	0.0140 (8)	0.0138 (7)	0.0085 (7)
C9	0.0413 (10)	0.0403 (11)	0.0247 (9)	0.0288 (9)	0.0174 (8)	0.0174 (8)
C10	0.0261 (9)	0.0532 (12)	0.0221 (8)	0.0187 (9)	0.0089 (7)	0.0148 (8)
C11	0.0264 (9)	0.0391 (10)	0.0164 (8)	0.0077 (8)	0.0065 (7)	0.0068 (7)
C12	0.0253 (8)	0.0254 (9)	0.0164 (7)	0.0073 (7)	0.0069 (6)	0.0048 (7)
C13	0.0251 (8)	0.0225 (8)	0.0138 (7)	0.0095 (7)	0.0107 (6)	0.0056 (6)
C14	0.0226 (8)	0.0167 (8)	0.0157 (7)	0.0061 (6)	0.0111 (6)	0.0039 (6)
C15	0.0176 (8)	0.0164 (8)	0.0173 (7)	0.0041 (6)	0.0075 (6)	0.0033 (6)
C16	0.0159 (7)	0.0143 (8)	0.0189 (7)	0.0049 (6)	0.0056 (6)	0.0059 (6)
C17	0.0197 (8)	0.0097 (7)	0.0197 (7)	0.0051 (6)	0.0056 (6)	0.0053 (6)
C18	0.0231 (8)	0.0166 (8)	0.0277 (8)	0.0078 (7)	0.0099 (7)	0.0057 (7)
C19	0.0395 (10)	0.0256 (9)	0.0255 (8)	0.0147 (8)	0.0168 (7)	0.0038 (7)
C20	0.0439 (10)	0.0219 (9)	0.0211 (8)	0.0095 (8)	0.0049 (7)	−0.0015 (7)
C21	0.0251 (8)	0.0180 (8)	0.0269 (8)	0.0029 (7)	0.0006 (7)	0.0008 (7)
C22	0.0216 (8)	0.0148 (8)	0.0224 (8)	0.0046 (6)	0.0079 (6)	0.0031 (6)

Geometric parameters (Å, º) top

N1—C15	1.4990 (17)	C10—H10	0.9300
N1—C16	1.5051 (18)	C11—C12	1.359 (2)
N1—H1A	0.917 (8)	C11—H11	0.9300
N1—H1B	0.922 (8)	C12—C13	1.426 (2)
C1—C14	1.410 (2)	C12—H12	0.9300
C1—C2	1.431 (2)	C13—C14	1.418 (2)
C1—C6	1.442 (2)	C14—C15	1.504 (2)
C2—C3	1.360 (2)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.421 (2)	C16—C17	1.512 (2)
C3—H3	0.9300	C16—H16A	0.9700
C4—C5	1.352 (2)	C16—H16B	0.9700
C4—H4	0.9300	C17—C22	1.386 (2)
C5—C6	1.425 (2)	C17—C18	1.3922 (19)
C5—H5	0.9300	C18—C19	1.391 (2)
C6—C7	1.394 (2)	C18—H18	0.9300
C7—C8	1.383 (2)	C19—C20	1.374 (2)
C7—H7	0.9300	C19—H19	0.9300
C8—C9	1.432 (2)	C20—C21	1.388 (2)
C8—C13	1.438 (2)	C20—H20	0.9300
C9—C10	1.353 (2)	C21—C22	1.386 (2)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.408 (2)	C22—H22	0.9300

C15—N1—C16	114.67 (10)	C11—C12—C13	121.55 (16)
C15—N1—H1A	112.3 (10)	C11—C12—H12	119.2
C16—N1—H1A	106.5 (10)	C13—C12—H12	119.2
C15—N1—H1B	109.8 (9)	C14—C13—C12	123.26 (14)
C16—N1—H1B	106.0 (9)	C14—C13—C8	119.31 (14)
H1A—N1—H1B	107.2 (9)	C12—C13—C8	117.42 (14)
C14—C1—C2	123.40 (14)	C1—C14—C13	120.77 (14)
C14—C1—C6	118.93 (14)	C1—C14—C15	120.96 (13)
C2—C1—C6	117.67 (14)	C13—C14—C15	118.23 (13)
C3—C2—C1	120.89 (16)	N1—C15—C14	112.01 (10)
C3—C2—H2	119.6	N1—C15—H15A	109.2
C1—C2—H2	119.6	C14—C15—H15A	109.2
C2—C3—C4	121.11 (16)	N1—C15—H15B	109.2
C2—C3—H3	119.4	C14—C15—H15B	109.2
C4—C3—H3	119.4	H15A—C15—H15B	107.9
C5—C4—C3	120.06 (16)	N1—C16—C17	111.53 (12)
C5—C4—H4	120.0	N1—C16—H16A	109.3
C3—C4—H4	120.0	C17—C16—H16A	109.3
C4—C5—C6	121.12 (16)	N1—C16—H16B	109.3
C4—C5—H5	119.4	C17—C16—H16B	109.3
C6—C5—H5	119.4	H16A—C16—H16B	108.0
C7—C6—C5	121.68 (15)	C22—C17—C18	119.11 (13)
C7—C6—C1	119.21 (15)	C22—C17—C16	120.99 (12)
C5—C6—C1	119.11 (15)	C18—C17—C16	119.88 (13)
C8—C7—C6	122.54 (15)	C19—C18—C17	120.05 (14)
C8—C7—H7	118.7	C19—C18—H18	120.0
C6—C7—H7	118.7	C17—C18—H18	120.0
C7—C8—C9	122.15 (15)	C20—C19—C18	120.37 (14)
C7—C8—C13	119.11 (14)	C20—C19—H19	119.8
C9—C8—C13	118.74 (15)	C18—C19—H19	119.8
C10—C9—C8	121.28 (16)	C19—C20—C21	120.05 (14)
C10—C9—H9	119.4	C19—C20—H20	120.0
C8—C9—H9	119.4	C21—C20—H20	120.0
C9—C10—C11	120.10 (15)	C22—C21—C20	119.72 (15)
C9—C10—H10	119.9	C22—C21—H21	120.1
C11—C10—H10	119.9	C20—C21—H21	120.1
C12—C11—C10	120.87 (16)	C17—C22—C21	120.71 (13)
C12—C11—H11	119.6	C17—C22—H22	119.6
C10—C11—H11	119.6	C21—C22—H22	119.6

C14—C1—C2—C3	−177.07 (13)	C7—C8—C13—C12	178.28 (12)
C6—C1—C2—C3	1.8 (2)	C9—C8—C13—C12	−1.57 (19)
C1—C2—C3—C4	−0.1 (2)	C2—C1—C14—C13	−178.15 (12)
C2—C3—C4—C5	−0.9 (2)	C6—C1—C14—C13	3.01 (19)
C3—C4—C5—C6	0.2 (2)	C2—C1—C14—C15	4.2 (2)
C4—C5—C6—C7	−178.11 (14)	C6—C1—C14—C15	−174.63 (12)
C4—C5—C6—C1	1.5 (2)	C12—C13—C14—C1	179.28 (12)
C14—C1—C6—C7	−3.89 (19)	C8—C13—C14—C1	0.21 (19)
C2—C1—C6—C7	177.20 (12)	C12—C13—C14—C15	−3.02 (19)
C14—C1—C6—C5	176.47 (12)	C8—C13—C14—C15	177.92 (12)
C2—C1—C6—C5	−2.44 (19)	C16—N1—C15—C14	−170.73 (11)
C5—C6—C7—C8	−178.83 (13)	C1—C14—C15—N1	−106.13 (14)
C1—C6—C7—C8	1.5 (2)	C13—C14—C15—N1	76.17 (15)
C6—C7—C8—C9	−178.44 (13)	C15—N1—C16—C17	52.24 (15)
C6—C7—C8—C13	1.7 (2)	N1—C16—C17—C22	81.05 (17)
C7—C8—C9—C10	−179.48 (14)	N1—C16—C17—C18	−97.18 (15)
C13—C8—C9—C10	0.4 (2)	C22—C17—C18—C19	−0.7 (2)
C8—C9—C10—C11	0.6 (2)	C16—C17—C18—C19	177.52 (14)
C9—C10—C11—C12	−0.4 (2)	C17—C18—C19—C20	0.6 (2)
C10—C11—C12—C13	−0.9 (2)	C18—C19—C20—C21	−0.1 (2)
C11—C12—C13—C14	−177.20 (13)	C19—C20—C21—C22	−0.2 (2)
C11—C12—C13—C8	1.9 (2)	C18—C17—C22—C21	0.5 (2)
C7—C8—C13—C14	−2.6 (2)	C16—C17—C22—C21	−177.76 (13)
C9—C8—C13—C14	177.55 (11)	C20—C21—C22—C17	0.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.92 (1)	2.26 (1)	3.0963 (13)	152 (1)
N1—H1B···Cl1	0.92 (1)	2.17 (1)	3.0781 (16)	170 (1)
C16—H16A···Cl1ⁱⁱ	0.97	2.60	3.4824 (16)	151

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N⁺·Cl⁻
M_r	333.84
Crystal system, space group	Triclinic, P1
Temperature (K)	113
a, b, c (Å)	6.7457 (13), 10.761 (2), 13.033 (3)
α, β, γ (°)	94.45 (3), 104.84 (3), 104.48 (3)
V (Å³)	875.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.28 × 0.24 × 0.20

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.941, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	5882, 3048, 2342
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.088, 1.04
No. of reflections	3048
No. of parameters	226
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1ⁱ	0.917 (8)	2.257 (11)	3.0963 (13)	151.9 (13)
N1—H1B···Cl1	0.922 (8)	2.165 (9)	3.0781 (16)	170.3 (12)
C16—H16A···Cl1ⁱⁱ	0.970	2.600	3.4824 (16)	151

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: chlsx@263.net.

Acknowledgements

We are grateful for financial support from the Hebei Natural Science Fundation (No. B2009000670) and the Foundation of the Education Department of Hebei Province (grant No. 2009117), People's Republic of China.

References

Ashton, P. R., Ballardini, R., Balzani, V., Marcos, G.-L., Lawrence, S. M., Victoria, M.-D., Montalti, M., Piersanti, A., Prodi, L., Stoddart, J. F. & Williams, D. (1997). J. Am. Chem. Soc. 119, 10641–10651. CrossRef CAS Google Scholar
Nakazono, K., Kuwata, S. & Takata, T. (2008). Tetrahedron Lett. 49, 2397–2400. CrossRef CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar