4,5-Diphenyl-2-p-tolyl-1H-imidazol-3-ium perchlorate

Zhang, L.

doi:10.1107/S1600536809024325

organic compounds

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Volume 65| Part 8| August 2009| Page o1766

doi:10.1107/S1600536809024325

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4,5-Diphenyl-2-p-tolyl-1H-imidazol-3-ium perchlorate

Li Zhang ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 22 June 2009; accepted 24 June 2009; online 4 July 2009)

In the title compound, C₂₂H₁₉N₂⁺·ClO₄⁻, the three pendant aromatic rings are twisted from the plane of the imidazolium ring by dihedral angles of 17.3 (2), 65.7 (2) and 3.4 (2)°. In the crystal structure, N—H⋯O and N—H⋯(O,O) hydrogen bonds link the ions, forming a ribbon-like structure along the a axis.

Related literature

For general background to imidazole derivatives, see: Fu & Xiong (2008 ); Huang et al. (2008 ). For applications of metal-organic coordination compounds, see: Fu et al. (2007 , 2008 ); Huang et al. (1999 ); Liu et al. (1999 ); Xie et al. (2003 ); Zhang et al. (2000 , 2001 ).

Experimental

Crystal data

C₂₂H₁₉N₂⁺·ClO₄⁻
M_r = 410.84
Monoclinic, P 2₁ /c
a = 9.1964 (18) Å
b = 9.921 (2) Å
c = 21.489 (4) Å
β = 94.16 (3)°
V = 1955.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.45 × 0.40 × 0.25 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.945, T_max = 1.000 (expected range = 0.893–0.945)
19242 measured reflections
4474 independent reflections
2602 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.214
S = 1.04
4474 reflections
271 parameters
24 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.89 (4)	2.05 (4)	2.943 (4)	175 (3)
N2—H2⋯O1ⁱⁱ	0.81 (4)	2.33 (4)	3.037 (5)	146 (3)
N2—H2⋯O1ⁱⁱⁱ	0.81 (4)	2.50 (4)	3.196 (5)	145 (3)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 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/S1600536809024325/ci2832sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024325/ci2832Isup2.hkl

checkCIF report

Comment top

The construction of metal-organic coordination compounds has attracted much attention owing to potential functions such as permittivity, fluorescence, magnetism and optical properties (Fu et al., 2007, 2008; Huang et al., 1999; Liu et al., 1999; Xie et al., 2003; Zhang et al., 2000, 2001). Imidazole derivatives are a class of excellent ligands because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Huang et al. 2008; Fu & Xiong 2008). We report here the crystal structure of the title compound, 4,5-diphenyl-2-p-tolyl-1H-imidazolium perchlorate.

The title compound contains an organic cation and a ClO₄^- anion in the asymmetric unit. The imidazole N atom in the 3-position is protonated. The C1-C6, C9-C14 and C17-C22 benzene rings form dihedral angles of 17.3 (2)°, 65.7 (2)° and 3.4 (2)°, respectively, with the imidazolium ring.

The crystal packing is stabilized by N—H···O hydrogen bonds which form a ribbon-like structure extending along the a axis (Table 1 and Fig. 2).

Related literature top

For general background to imidazole derivatives, see: Fu & Xiong (2008); Huang et al. (2008). For applications of metal-organic coordination compounds, see: Fu et al. (2007, 2008); Huang et al. (1999); Liu et al. (1999); Xie et al. (2003); Zhang et al. (2000, 2001).

Experimental top

1,2-Diphenyl-ethane-1,2-dione (20 mmol), 4-methylbenzaldehyde (20 mmol) and amine acetate (50 mmol) were dissolved in 60 ml of HOAc under nitrogen protection. The mixture was stirred at 383 K for 20 h. The resulting solution was poured into ice water (200 ml) and after neutralizing the mixture with NaOH (6 mol/L) a white solid was obtained. The crude product was filtered and washed with distilled water. The crude product was dissolved in ethanol (150 ml)-perchloric acid (1 ml) and recrystallized to yield colourless block-shaped crystals of the title compound.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 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 compound, with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.
	Fig. 2. A hydrogen-bonded (dashed lines) ribbon in the title compound. H atoms not involved in hydrogen bonding have been omitted for clarity.

4,5-Diphenyl-2-p-tolyl-1H-imidazol-3-ium perchlorate top

Crystal data top

C₂₂H₁₉N₂⁺·ClO₄⁻	F(000) = 856
M_r = 410.84	D_x = 1.396 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2602 reflections
a = 9.1964 (18) Å	θ = 3.0–27.5°
b = 9.921 (2) Å	µ = 0.23 mm⁻¹
c = 21.489 (4) Å	T = 298 K
β = 94.16 (3)°	Block, colourless
V = 1955.4 (7) Å³	0.45 × 0.40 × 0.25 mm
Z = 4

Data collection top

Rigaku Mercury2 diffractometer	4474 independent reflections
Radiation source: fine-focus sealed tube	2602 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
CCD profile fitting scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −12→12
T_min = 0.945, T_max = 1.000	l = −27→27
19242 measured reflections

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.214	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.103P)² + 0.7747P] where P = (F_o² + 2F_c²)/3
4474 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.54 e Å⁻³
24 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₂H₁₉N₂⁺·ClO₄⁻	V = 1955.4 (7) Å³
M_r = 410.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.1964 (18) Å	µ = 0.23 mm⁻¹
b = 9.921 (2) Å	T = 298 K
c = 21.489 (4) Å	0.45 × 0.40 × 0.25 mm
β = 94.16 (3)°

Data collection top

Rigaku Mercury2 diffractometer	4474 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2602 reflections with I > 2σ(I)
T_min = 0.945, T_max = 1.000	R_int = 0.070
19242 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	24 restraints
wR(F²) = 0.214	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.54 e Å⁻³
4474 reflections	Δρ_min = −0.35 e Å⁻³
271 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	0.4669 (3)	0.2183 (3)	0.48657 (13)	0.0395 (7)
H1	0.549 (4)	0.216 (3)	0.4671 (16)	0.042 (9)*
N2	0.2652 (3)	0.1423 (3)	0.51476 (13)	0.0438 (7)
H2	0.186 (4)	0.106 (4)	0.5140 (16)	0.045 (11)*
C1	0.3452 (3)	0.0484 (3)	0.41492 (15)	0.0396 (8)
C2	0.4283 (4)	0.0746 (4)	0.36447 (17)	0.0570 (10)
H2A	0.4916	0.1478	0.3658	0.068*
C3	0.4170 (4)	−0.0072 (5)	0.31297 (18)	0.0643 (11)
H3	0.4739	0.0112	0.2799	0.077*
C4	0.3242 (4)	−0.1154 (4)	0.30873 (17)	0.0510 (9)
C5	0.2414 (4)	−0.1400 (4)	0.35845 (18)	0.0563 (10)
H5	0.1777	−0.2130	0.3565	0.068*
C6	0.2499 (4)	−0.0604 (4)	0.41063 (17)	0.0505 (9)
H6	0.1918	−0.0791	0.4432	0.061*
C7	0.3166 (6)	−0.2061 (5)	0.2522 (2)	0.0741 (13)
H7A	0.4118	−0.2416	0.2464	0.111*
H7B	0.2827	−0.1554	0.2160	0.111*
H7C	0.2505	−0.2791	0.2583	0.111*
C8	0.3585 (3)	0.1336 (3)	0.47026 (15)	0.0408 (8)
C9	0.2290 (4)	0.2630 (4)	0.61419 (16)	0.0452 (8)
C10	0.1687 (4)	0.3869 (4)	0.62354 (19)	0.0593 (10)
H10	0.1754	0.4537	0.5935	0.071*
C11	0.0982 (5)	0.4148 (6)	0.6766 (2)	0.0774 (14)
H11	0.0572	0.4993	0.6820	0.093*
C12	0.0891 (5)	0.3171 (7)	0.7213 (2)	0.0850 (17)
H12	0.0471	0.3368	0.7583	0.102*
C13	0.1420 (6)	0.1908 (7)	0.7113 (2)	0.0880 (17)
H13	0.1301	0.1232	0.7405	0.106*
C14	0.2135 (5)	0.1619 (5)	0.65781 (18)	0.0642 (11)
H14	0.2502	0.0760	0.6515	0.077*
C15	0.3122 (4)	0.2354 (3)	0.55912 (15)	0.0416 (8)
C16	0.4426 (3)	0.2849 (3)	0.54164 (15)	0.0380 (7)
C17	0.5461 (4)	0.3845 (3)	0.56847 (15)	0.0398 (8)
C18	0.6681 (4)	0.4211 (4)	0.53799 (17)	0.0486 (9)
H18	0.6836	0.3813	0.4999	0.058*
C19	0.7659 (4)	0.5140 (4)	0.56250 (18)	0.0556 (10)
H19	0.8470	0.5355	0.5411	0.067*
C20	0.7458 (4)	0.5755 (4)	0.61809 (18)	0.0551 (10)
H20	0.8123	0.6392	0.6344	0.066*
C21	0.6265 (4)	0.5421 (5)	0.64936 (19)	0.0679 (12)
H21	0.6116	0.5841	0.6871	0.082*
C22	0.5274 (4)	0.4466 (5)	0.62564 (18)	0.0624 (11)
H22	0.4480	0.4236	0.6480	0.075*
Cl1	0.11229 (9)	0.69744 (9)	0.07737 (4)	0.0502 (3)
O1	0.0560 (4)	0.5809 (4)	0.04536 (19)	0.1035 (12)
O2	0.0600 (4)	0.8046 (4)	0.0390 (2)	0.1247 (16)
O3	0.2657 (3)	0.6929 (4)	0.07995 (16)	0.0939 (12)
O4	0.0591 (4)	0.7023 (5)	0.13600 (17)	0.1216 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0325 (15)	0.0463 (17)	0.0409 (16)	−0.0013 (12)	0.0100 (12)	−0.0018 (13)
N2	0.0372 (16)	0.0509 (18)	0.0446 (16)	−0.0107 (14)	0.0112 (13)	−0.0063 (14)
C1	0.0344 (17)	0.0446 (19)	0.0403 (18)	0.0016 (14)	0.0051 (14)	−0.0009 (15)
C2	0.058 (2)	0.063 (2)	0.052 (2)	−0.0193 (19)	0.0177 (18)	−0.0104 (19)
C3	0.065 (3)	0.082 (3)	0.049 (2)	−0.011 (2)	0.0218 (19)	−0.015 (2)
C4	0.052 (2)	0.054 (2)	0.046 (2)	0.0043 (18)	−0.0002 (17)	−0.0066 (17)
C5	0.057 (2)	0.056 (2)	0.056 (2)	−0.0138 (19)	0.0006 (19)	−0.0072 (19)
C6	0.049 (2)	0.058 (2)	0.045 (2)	−0.0116 (18)	0.0103 (16)	−0.0029 (18)
C7	0.096 (4)	0.070 (3)	0.056 (3)	−0.003 (2)	0.004 (2)	−0.016 (2)
C8	0.0341 (17)	0.048 (2)	0.0406 (18)	0.0012 (15)	0.0067 (14)	0.0030 (15)
C9	0.0343 (17)	0.062 (2)	0.0396 (18)	−0.0046 (16)	0.0069 (14)	−0.0052 (17)
C10	0.055 (2)	0.065 (3)	0.060 (2)	0.0018 (19)	0.0207 (19)	−0.005 (2)
C11	0.062 (3)	0.099 (4)	0.073 (3)	0.005 (2)	0.021 (2)	−0.030 (3)
C12	0.053 (3)	0.151 (5)	0.053 (3)	−0.010 (3)	0.020 (2)	−0.034 (3)
C13	0.078 (3)	0.143 (5)	0.045 (2)	−0.012 (3)	0.017 (2)	0.018 (3)
C14	0.067 (3)	0.077 (3)	0.050 (2)	−0.001 (2)	0.013 (2)	0.008 (2)
C15	0.0412 (18)	0.0467 (19)	0.0379 (18)	−0.0004 (15)	0.0084 (14)	−0.0002 (15)
C16	0.0358 (17)	0.0428 (18)	0.0359 (17)	0.0023 (14)	0.0064 (13)	−0.0002 (14)
C17	0.0366 (17)	0.0443 (19)	0.0387 (17)	0.0017 (14)	0.0040 (14)	0.0020 (15)
C18	0.045 (2)	0.059 (2)	0.0428 (19)	−0.0067 (17)	0.0105 (16)	−0.0056 (17)
C19	0.044 (2)	0.066 (3)	0.057 (2)	−0.0101 (19)	0.0080 (18)	0.006 (2)
C20	0.050 (2)	0.057 (2)	0.057 (2)	−0.0120 (18)	−0.0031 (18)	−0.0045 (19)
C21	0.065 (3)	0.086 (3)	0.054 (2)	−0.016 (2)	0.007 (2)	−0.027 (2)
C22	0.050 (2)	0.091 (3)	0.049 (2)	−0.020 (2)	0.0150 (18)	−0.016 (2)
Cl1	0.0404 (5)	0.0565 (6)	0.0555 (6)	0.0032 (4)	0.0167 (4)	−0.0080 (4)
O1	0.093 (3)	0.089 (2)	0.130 (3)	−0.006 (2)	0.021 (2)	−0.043 (2)
O2	0.083 (3)	0.108 (3)	0.185 (4)	0.032 (2)	0.023 (3)	0.064 (3)
O3	0.0401 (16)	0.152 (3)	0.091 (2)	0.0059 (18)	0.0130 (15)	0.033 (2)
O4	0.093 (3)	0.206 (4)	0.070 (2)	−0.018 (3)	0.038 (2)	−0.037 (3)

Geometric parameters (Å, º) top

N1—C8	1.332 (4)	C10—H10	0.93
N1—C16	1.387 (4)	C11—C12	1.372 (7)
N1—H1	0.89 (4)	C11—H11	0.93
N2—C8	1.333 (4)	C12—C13	1.367 (8)
N2—C15	1.374 (4)	C12—H12	0.93
N2—H2	0.81 (4)	C13—C14	1.394 (6)
C1—C6	1.389 (5)	C13—H13	0.93
C1—C2	1.396 (5)	C14—H14	0.93
C1—C8	1.457 (5)	C15—C16	1.374 (4)
C2—C3	1.371 (5)	C16—C17	1.461 (5)
C2—H2A	0.93	C17—C18	1.388 (5)
C3—C4	1.370 (5)	C17—C22	1.396 (5)
C3—H3	0.93	C18—C19	1.366 (5)
C4—C5	1.378 (5)	C18—H18	0.93
C4—C7	1.509 (5)	C19—C20	1.366 (5)
C5—C6	1.370 (5)	C19—H19	0.93
C5—H5	0.93	C20—C21	1.369 (5)
C6—H6	0.93	C20—H20	0.93
C7—H7A	0.96	C21—C22	1.386 (5)
C7—H7B	0.96	C21—H21	0.93
C7—H7C	0.96	C22—H22	0.93
C9—C10	1.370 (5)	Cl1—O4	1.385 (3)
C9—C14	1.387 (5)	Cl1—O2	1.408 (4)
C9—C15	1.481 (4)	Cl1—O3	1.409 (3)
C10—C11	1.379 (5)	Cl1—O1	1.424 (3)

C8—N1—C16	111.2 (3)	C10—C11—H11	120.2
C8—N1—H1	120 (2)	C13—C12—C11	119.7 (4)
C16—N1—H1	127 (2)	C13—C12—H12	120.1
C8—N2—C15	110.8 (3)	C11—C12—H12	120.1
C8—N2—H2	125 (3)	C12—C13—C14	120.9 (5)
C15—N2—H2	123 (2)	C12—C13—H13	119.6
C6—C1—C2	118.1 (3)	C14—C13—H13	119.6
C6—C1—C8	121.3 (3)	C9—C14—C13	119.1 (5)
C2—C1—C8	120.5 (3)	C9—C14—H14	120.5
C3—C2—C1	120.2 (4)	C13—C14—H14	120.5
C3—C2—H2A	119.9	C16—C15—N2	106.7 (3)
C1—C2—H2A	119.9	C16—C15—C9	131.6 (3)
C4—C3—C2	121.9 (4)	N2—C15—C9	121.6 (3)
C4—C3—H3	119.0	C15—C16—N1	105.1 (3)
C2—C3—H3	119.0	C15—C16—C17	133.7 (3)
C3—C4—C5	117.6 (3)	N1—C16—C17	121.2 (3)
C3—C4—C7	120.9 (4)	C18—C17—C22	117.1 (3)
C5—C4—C7	121.5 (4)	C18—C17—C16	121.1 (3)
C6—C5—C4	122.1 (4)	C22—C17—C16	121.8 (3)
C6—C5—H5	119.0	C19—C18—C17	121.8 (3)
C4—C5—H5	119.0	C19—C18—H18	119.1
C5—C6—C1	120.1 (3)	C17—C18—H18	119.1
C5—C6—H6	120.0	C20—C19—C18	120.8 (4)
C1—C6—H6	120.0	C20—C19—H19	119.6
C4—C7—H7A	109.5	C18—C19—H19	119.6
C4—C7—H7B	109.5	C19—C20—C21	119.0 (4)
H7A—C7—H7B	109.5	C19—C20—H20	120.5
C4—C7—H7C	109.5	C21—C20—H20	120.5
H7A—C7—H7C	109.5	C20—C21—C22	121.0 (4)
H7B—C7—H7C	109.5	C20—C21—H21	119.5
N1—C8—N2	106.2 (3)	C22—C21—H21	119.5
N1—C8—C1	126.7 (3)	C21—C22—C17	120.4 (4)
N2—C8—C1	127.1 (3)	C21—C22—H22	119.8
C10—C9—C14	119.2 (3)	C17—C22—H22	119.8
C10—C9—C15	121.4 (3)	O4—Cl1—O2	112.2 (3)
C14—C9—C15	119.4 (3)	O4—Cl1—O3	112.6 (2)
C9—C10—C11	121.4 (4)	O2—Cl1—O3	110.2 (2)
C9—C10—H10	119.3	O4—Cl1—O1	109.1 (2)
C11—C10—H10	119.3	O2—Cl1—O1	103.5 (3)
C12—C11—C10	119.6 (5)	O3—Cl1—O1	108.7 (2)
C12—C11—H11	120.2

C6—C1—C2—C3	−1.2 (6)	C12—C13—C14—C9	−0.8 (7)
C8—C1—C2—C3	178.9 (4)	C8—N2—C15—C16	−1.1 (4)
C1—C2—C3—C4	0.6 (7)	C8—N2—C15—C9	−179.1 (3)
C2—C3—C4—C5	0.0 (6)	C10—C9—C15—C16	66.3 (5)
C2—C3—C4—C7	−178.4 (4)	C14—C9—C15—C16	−112.8 (5)
C3—C4—C5—C6	0.0 (6)	C10—C9—C15—N2	−116.2 (4)
C7—C4—C5—C6	178.4 (4)	C14—C9—C15—N2	64.7 (5)
C4—C5—C6—C1	−0.6 (6)	N2—C15—C16—N1	0.4 (4)
C2—C1—C6—C5	1.2 (5)	C9—C15—C16—N1	178.1 (3)
C8—C1—C6—C5	−178.9 (3)	N2—C15—C16—C17	−180.0 (3)
C16—N1—C8—N2	−1.1 (4)	C9—C15—C16—C17	−2.2 (7)
C16—N1—C8—C1	179.0 (3)	C8—N1—C16—C15	0.5 (4)
C15—N2—C8—N1	1.4 (4)	C8—N1—C16—C17	−179.2 (3)
C15—N2—C8—C1	−178.7 (3)	C15—C16—C17—C18	−176.1 (4)
C6—C1—C8—N1	162.8 (3)	N1—C16—C17—C18	3.5 (5)
C2—C1—C8—N1	−17.4 (5)	C15—C16—C17—C22	4.1 (6)
C6—C1—C8—N2	−17.1 (5)	N1—C16—C17—C22	−176.2 (3)
C2—C1—C8—N2	162.7 (4)	C22—C17—C18—C19	−0.2 (6)
C14—C9—C10—C11	2.7 (6)	C16—C17—C18—C19	−179.9 (3)
C15—C9—C10—C11	−176.3 (4)	C17—C18—C19—C20	−0.7 (6)
C9—C10—C11—C12	0.6 (7)	C18—C19—C20—C21	0.5 (6)
C10—C11—C12—C13	−4.0 (7)	C19—C20—C21—C22	0.6 (7)
C11—C12—C13—C14	4.1 (7)	C20—C21—C22—C17	−1.4 (7)
C10—C9—C14—C13	−2.6 (6)	C18—C17—C22—C21	1.2 (6)
C15—C9—C14—C13	176.5 (4)	C16—C17—C22—C21	−179.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.89 (4)	2.05 (4)	2.943 (4)	175 (3)
N2—H2···O1ⁱⁱ	0.81 (4)	2.33 (4)	3.037 (5)	146 (3)
N2—H2···O1ⁱⁱⁱ	0.81 (4)	2.50 (4)	3.196 (5)	145 (3)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₉N₂⁺·ClO₄⁻
M_r	410.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	9.1964 (18), 9.921 (2), 21.489 (4)
β (°)	94.16 (3)
V (Å³)	1955.4 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.45 × 0.40 × 0.25

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.945, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	19242, 4474, 2602
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.214, 1.04
No. of reflections	4474
No. of parameters	271
No. of restraints	24
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.35

Computer programs: CrystalClear (Rigaku, 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—H1···O3ⁱ	0.89 (4)	2.05 (4)	2.943 (4)	175 (3)
N2—H2···O1ⁱⁱ	0.81 (4)	2.33 (4)	3.037 (5)	146 (3)
N2—H2···O1ⁱⁱⁱ	0.81 (4)	2.50 (4)	3.196 (5)	145 (3)

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) x, −y+1/2, z+1/2; (iii) −x, y−1/2, −z+1/2.

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

References

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