1-{4-[(1H-1,2,4-Triazol-1-yl)meth­yl]benz­yl}-1H-1,2,4-triazol-4-ium perchlorate

Hu, Z.-J.; Guo, X.-K.; Xu, H.; He, M.-Y.; Geng, L.

doi:10.1107/S1600536810002618

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o537

doi:10.1107/S1600536810002618

Open

access

1-{4-[(1H-1,2,4-Triazol-1-yl)methyl]benzyl}-1H-1,2,4-triazol-4-ium perchlorate

Zhao-Jian Hu,^a Xiu-Kai Guo,^a Huan Xu,^a Ming-Yang He ^a ^* and Li Geng ^a

^aKey Laboratory of Fine Petrochemical Technology, Jiangsu Polytechnic University, Changzhou 213164, People's Republic of China
^*Correspondence e-mail: hemingyangjpu@yahoo.com

(Received 1 January 2010; accepted 21 January 2010; online 6 February 2010)

In the crystal structure of the title compound, C₁₂H₁₃N₆⁺·ClO₄⁻, the cation, located about an inversion center, is monoprotonated, and one H atom is disordered over two sites on N atoms of the two triazole rings, each with an occupancy factor of 0.5. The perchlorate anion has C₂ symmetry, the Cl atom and one O atom lying on the twofold rotation axis; the anion is thus disordered over two sites of equal occupancy. In the cation, the triazole ring makes a dihedral angle of 84.75 (7)° with the plane of the benzene ring. In the crystal, intermolecular N—H⋯N hydrogen bonding between the triazole and triazolium rings links the cations into a wave-like supramolecular chain. Weak intermolecular C—H⋯N and C—H⋯O hydrogen bonding is also present.

Related literature

For the versatile conformations of the flexible 1,4-bis(1,2,4-triazol-1-yl-methyl)benzene ligand, see: Arion et al. (2003 ); Peng et al. (2004 , 2006 ); Meng et al. (2004 ); Li et al. (2005 ); Ding et al. (2009 ).

Experimental

Crystal data

C₁₂H₁₃N₆⁺·ClO₄⁻
M_r = 340.73
Monoclinic, C 2/c
a = 15.140 (5) Å
b = 11.362 (3) Å
c = 10.408 (3) Å
β = 124.500 (5)°
V = 1475.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 297 K
0.20 × 0.15 × 0.14 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.944, T_max = 0.961
4272 measured reflections
1436 independent reflections
1215 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.139
S = 1.09
1436 reflections
120 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N3ⁱ	0.86	1.86	2.690 (5)	162
C1—H1⋯O4ⁱⁱ	0.93	2.54	3.445 (12)	164
C3—H3⋯O2ⁱⁱⁱ	0.93	2.55	3.403 (15)	152
C4—H4A⋯O4^iv	0.97	2.46	3.430 (15)	176
C6—H6⋯N2^iv	0.93	2.55	3.256 (4)	133
Symmetry codes: (i) $[-x, y, -z+{\script{3\over 2}}]$ ; (ii) -x+1, -y, -z+1; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x, -y, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810002618/xu2715sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810002618/xu2715Isup2.hkl

checkCIF report

Comment top

In recent years, there has been of great interest in the design and utilization of 1,2,4-triazole and its derivatives in coordination and biological chemistry for they represent the simple small molecular ligands. Among them, 1,4-Bis(1,2,4-triazol-1-yl-methyl)benzene (L) has attracted significant attention because of its versatile conformations arising from the flexible rotation of σ bonds of two methylene carbon atoms (C_sp3) between the terminal triazole groups and the benzene ring (Arion, et al., 2003; Peng, et al., 2004, 2006; Meng, et al., 2004; Li et al., 2005; Ding, et al. 2009). To further understand the supramolecular behavior of this ligand, we report herein the crystal structure of the title compound, [C₁₂H₁₃N₆]⁺.ClO₄^-(I).

A perspective view of (I), including the atomic numbering scheme, is shown in Figure 1. The monoprotonated cationic HL⁺ moiety of compound (I) crystallizes around an inversion center with a half molecule in the asymmetric unit. The anionic perchlorate is disorder over two positions related by a C₂ axis, which crosses Cl1 and O3 atoms. Within each discrete tran-configurational cation, the triazole/triazolium ring makes a dihedral angle of 84.75 (7)° with the central benzene ring. Strong N—H···N interactions between triazole and triazolium groups join these cationic molecules into an infinite wavelike chain running along the crystallographic [1 0 1] direction (Figure 2). The final crystal structure results in a three-dimensional (3-D) hydrogen bonding network through the linkage of multiple C—H···N and C—H···O hydrogen bonds between the cationic subunits and perchlorate anions (Table 1).

Related literature top

For the versatile conformations of the flexible 1,4-bis(1,2,4-triazol-1-yl-methyl)benzene ligand, see: Arion et al. (2003); Peng et al. (2004, 2006); Meng et al. (2004); Li et al. (2005); Ding et al. (2009).

Experimental top

Zn(ClO₄)_2.6H₂O (74 mg, 0.2 mmol) and 1,4-bis(1,2,4-triazol-1-yl-methyl)benzene (L) (48 mg, 0.2 mmol) was dissolved in a 8 ml ethanol-water mixture (V:V = 1:3) at room temperature. The colorless crystals were obtained after several days. Yield: 60% (based on L).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecule of (I). Displacement ellipsoids are drawn at the 30% probability level. Symmetry code: (A) -x + 1/2, -y + 1/2, -z + 1.
	Fig. 2. A one-dimensional hydrogen-bonding chain motif of (I).

1-{4-[(1H-1,2,4-Triazol-1-yl)methyl]benzyl}-1H- 1,2,4-triazol-4-ium perchlorate top

Crystal data top

C₁₂H₁₃N₆⁺·ClO₄⁻	F(000) = 704
M_r = 340.73	D_x = 1.534 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1942 reflections
a = 15.140 (5) Å	θ = 2.4–27.5°
b = 11.362 (3) Å	µ = 0.29 mm⁻¹
c = 10.408 (3) Å	T = 297 K
β = 124.500 (5)°	Block, colorless
V = 1475.5 (7) Å³	0.20 × 0.15 × 0.14 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1436 independent reflections
Radiation source: fine-focus sealed tube	1215 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→18
T_min = 0.944, T_max = 0.961	k = −13→13
4272 measured reflections	l = −12→12

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0491P)² + 2.663P] where P = (F_o² + 2F_c²)/3
1436 reflections	(Δ/σ)_max < 0.001
120 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

C₁₂H₁₃N₆⁺·ClO₄⁻	V = 1475.5 (7) Å³
M_r = 340.73	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 15.140 (5) Å	µ = 0.29 mm⁻¹
b = 11.362 (3) Å	T = 297 K
c = 10.408 (3) Å	0.20 × 0.15 × 0.14 mm
β = 124.500 (5)°

Data collection top

Bruker APEXII CCD diffractometer	1436 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1215 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.961	R_int = 0.021
4272 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.09	Δρ_max = 0.28 e Å⁻³
1436 reflections	Δρ_min = −0.61 e Å⁻³
120 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	Occ. (<1)
C1	0.3304 (2)	0.1668 (2)	0.5558 (3)	0.0423 (6)
H1	0.3848	0.1112	0.5929	0.051*
C2	0.27311 (19)	0.1755 (2)	0.6225 (3)	0.0388 (5)
C3	0.19301 (19)	0.2594 (2)	0.5662 (3)	0.0417 (6)
H3	0.1545	0.2665	0.6106	0.050*
C4	0.3004 (2)	0.0963 (3)	0.7575 (3)	0.0526 (7)
H4A	0.3578	0.0433	0.7799	0.063*
H4B	0.3260	0.1441	0.8494	0.063*
C6	0.1572 (2)	0.0310 (2)	0.7933 (3)	0.0495 (6)
H6	0.1735	0.0809	0.8748	0.059*
C5	0.0862 (2)	−0.0993 (2)	0.6166 (3)	0.0471 (6)
H5	0.0403	−0.1588	0.5514	0.057*
N1	0.20807 (16)	0.02713 (17)	0.7242 (2)	0.0416 (5)
N2	0.16400 (17)	−0.05709 (19)	0.6103 (2)	0.0466 (5)
N3	0.07910 (18)	−0.0479 (2)	0.7274 (3)	0.0506 (6)
H3A	0.0338	−0.0630	0.7501	0.061*	0.50
Cl1	0.5000	0.16865 (9)	0.2500	0.0749 (4)
O1	0.3684 (4)	0.1843 (5)	0.1366 (6)	0.0902 (16)	0.50
O2	0.5109 (9)	0.1370 (12)	0.1316 (12)	0.136 (5)	0.50
O3	0.5000	0.2786 (5)	0.2500	0.254 (5)
O4	0.5108 (10)	0.0799 (8)	0.3416 (13)	0.122 (3)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0410 (12)	0.0427 (13)	0.0453 (13)	0.0003 (10)	0.0257 (11)	−0.0002 (10)
C2	0.0408 (12)	0.0412 (12)	0.0334 (11)	−0.0083 (10)	0.0203 (10)	−0.0022 (9)
C3	0.0451 (13)	0.0479 (13)	0.0432 (13)	−0.0057 (10)	0.0316 (11)	−0.0048 (10)
C4	0.0472 (14)	0.0639 (17)	0.0379 (13)	−0.0091 (13)	0.0188 (11)	0.0072 (12)
C6	0.0652 (17)	0.0506 (14)	0.0467 (14)	0.0094 (13)	0.0400 (13)	0.0098 (11)
C5	0.0482 (14)	0.0473 (14)	0.0451 (13)	−0.0006 (11)	0.0260 (12)	0.0074 (11)
N1	0.0500 (11)	0.0451 (11)	0.0342 (10)	−0.0005 (9)	0.0266 (9)	0.0069 (8)
N2	0.0533 (12)	0.0522 (12)	0.0382 (10)	−0.0024 (10)	0.0283 (10)	0.0015 (9)
N3	0.0535 (13)	0.0567 (13)	0.0569 (13)	0.0105 (11)	0.0405 (11)	0.0181 (11)
Cl1	0.1341 (12)	0.0393 (5)	0.0914 (9)	0.000	0.0878 (9)	0.000
O1	0.049 (2)	0.122 (4)	0.085 (3)	0.014 (3)	0.030 (3)	−0.006 (3)
O2	0.096 (6)	0.252 (15)	0.073 (4)	0.022 (8)	0.055 (4)	−0.004 (7)
O3	0.283 (10)	0.061 (3)	0.401 (14)	0.000	0.183 (10)	0.000
O4	0.129 (7)	0.105 (6)	0.120 (7)	0.012 (5)	0.064 (6)	0.061 (5)

Geometric parameters (Å, º) top

C1—C2	1.388 (3)	C5—N3	1.350 (3)
C1—C3ⁱ	1.389 (3)	C5—H5	0.9300
C1—H1	0.9300	N1—N2	1.367 (3)
C2—C3	1.385 (3)	N3—H3A	0.8600
C2—C4	1.515 (3)	Cl1—O3	1.249 (5)
C3—C1ⁱ	1.389 (3)	Cl1—O4ⁱⁱ	1.333 (8)
C3—H3	0.9300	Cl1—O4	1.333 (8)
C4—N1	1.464 (3)	Cl1—O2	1.381 (9)
C4—H4A	0.9700	Cl1—O2ⁱⁱ	1.381 (9)
C4—H4B	0.9700	Cl1—O1ⁱⁱ	1.653 (5)
C6—N1	1.319 (3)	Cl1—O1	1.653 (4)
C6—N3	1.324 (4)	O2—O4ⁱⁱ	0.843 (13)
C6—H6	0.9300	O4—O2ⁱⁱ	0.843 (13)
C5—N2	1.308 (3)	O4—O4ⁱⁱ	1.74 (2)

C2—C1—C3ⁱ	120.4 (2)	C6—N3—H3A	127.6
C2—C1—H1	119.8	C5—N3—H3A	127.6
C3ⁱ—C1—H1	119.8	O3—Cl1—O4ⁱⁱ	139.2 (5)
C3—C2—C1	118.9 (2)	O3—Cl1—O4	139.2 (5)
C3—C2—C4	121.0 (2)	O4ⁱⁱ—Cl1—O4	81.7 (10)
C1—C2—C4	120.1 (2)	O3—Cl1—O2	105.1 (5)
C2—C3—C1ⁱ	120.7 (2)	O4—Cl1—O2	114.4 (8)
C2—C3—H3	119.6	O3—Cl1—O2ⁱⁱ	105.1 (5)
C1ⁱ—C3—H3	119.6	O4ⁱⁱ—Cl1—O2ⁱⁱ	114.4 (8)
N1—C4—C2	112.1 (2)	O2—Cl1—O2ⁱⁱ	149.8 (11)
N1—C4—H4A	109.2	O3—Cl1—O1ⁱⁱ	83.8 (2)
C2—C4—H4A	109.2	O4ⁱⁱ—Cl1—O1ⁱⁱ	101.6 (6)
N1—C4—H4B	109.2	O4—Cl1—O1ⁱⁱ	87.8 (6)
C2—C4—H4B	109.2	O2—Cl1—O1ⁱⁱ	87.7 (5)
H4A—C4—H4B	107.9	O2ⁱⁱ—Cl1—O1ⁱⁱ	95.5 (5)
N1—C6—N3	108.7 (2)	O3—Cl1—O1	83.8 (2)
N1—C6—H6	125.6	O4ⁱⁱ—Cl1—O1	87.8 (6)
N3—C6—H6	125.6	O4—Cl1—O1	101.6 (6)
N2—C5—N3	113.2 (2)	O2—Cl1—O1	95.5 (5)
N2—C5—H5	123.4	O2ⁱⁱ—Cl1—O1	87.7 (5)
N3—C5—H5	123.4	O1ⁱⁱ—Cl1—O1	167.6 (4)
C6—N1—N2	110.3 (2)	O4ⁱⁱ—O2—Cl1	68.8 (9)
C6—N1—C4	128.9 (2)	O2ⁱⁱ—O4—Cl1	75.0 (11)
N2—N1—C4	120.8 (2)	O2ⁱⁱ—O4—O4ⁱⁱ	119.7 (14)
C5—N2—N1	103.0 (2)	Cl1—O4—O4ⁱⁱ	49.2 (5)
C6—N3—C5	104.8 (2)

C3ⁱ—C1—C2—C3	−0.5 (4)	O3—Cl1—O2—O4ⁱⁱ	−163.6 (14)
C3ⁱ—C1—C2—C4	−178.9 (2)	O4—Cl1—O2—O4ⁱⁱ	27 (2)
C1—C2—C3—C1ⁱ	0.5 (4)	O2ⁱⁱ—Cl1—O2—O4ⁱⁱ	16.4 (14)
C4—C2—C3—C1ⁱ	178.8 (2)	O1ⁱⁱ—Cl1—O2—O4ⁱⁱ	113.4 (15)
C3—C2—C4—N1	58.5 (3)	O1—Cl1—O2—O4ⁱⁱ	−78.6 (15)
C1—C2—C4—N1	−123.1 (3)	O3—Cl1—O4—O2ⁱⁱ	25 (2)
N3—C6—N1—N2	−0.7 (3)	O4ⁱⁱ—Cl1—O4—O2ⁱⁱ	−155 (2)
N3—C6—N1—C4	−179.2 (2)	O2—Cl1—O4—O2ⁱⁱ	−171.0 (9)
C2—C4—N1—C6	−115.6 (3)	O1ⁱⁱ—Cl1—O4—O2ⁱⁱ	102.5 (15)
C2—C4—N1—N2	66.0 (3)	O1—Cl1—O4—O2ⁱⁱ	−69.4 (15)
N3—C5—N2—N1	−0.5 (3)	O3—Cl1—O4—O4ⁱⁱ	180.000 (3)
C6—N1—N2—C5	0.7 (3)	O2—Cl1—O4—O4ⁱⁱ	−15.6 (12)
C4—N1—N2—C5	179.3 (2)	O2ⁱⁱ—Cl1—O4—O4ⁱⁱ	155 (2)
N1—C6—N3—C5	0.3 (3)	O1ⁱⁱ—Cl1—O4—O4ⁱⁱ	−102.1 (6)
N2—C5—N3—C6	0.1 (3)	O1—Cl1—O4—O4ⁱⁱ	86.0 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N3ⁱⁱⁱ	0.86	1.86	2.690 (5)	162
C1—H1···O4^iv	0.93	2.54	3.445 (12)	164
C3—H3···O2^v	0.93	2.55	3.403 (15)	152
C4—H4A···O4^vi	0.97	2.46	3.430 (15)	176
C6—H6···N2^vi	0.93	2.55	3.256 (4)	133

Symmetry codes: (iii) −x, y, −z+3/2; (iv) −x+1, −y, −z+1; (v) x−1/2, −y+1/2, z+1/2; (vi) x, −y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃N₆⁺·ClO₄⁻
M_r	340.73
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	297
a, b, c (Å)	15.140 (5), 11.362 (3), 10.408 (3)
β (°)	124.500 (5)
V (Å³)	1475.5 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.20 × 0.15 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.944, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	4272, 1436, 1215
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.139, 1.09
No. of reflections	1436
No. of parameters	120
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.61

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N3ⁱ	0.86	1.86	2.690 (5)	162
C1—H1···O4ⁱⁱ	0.93	2.54	3.445 (12)	164
C3—H3···O2ⁱⁱⁱ	0.93	2.55	3.403 (15)	152
C4—H4A···O4^iv	0.97	2.46	3.430 (15)	176
C6—H6···N2^iv	0.93	2.55	3.256 (4)	133

Symmetry codes: (i) −x, y, −z+3/2; (ii) −x+1, −y, −z+1; (iii) x−1/2, −y+1/2, z+1/2; (iv) x, −y, z+1/2.

References

Arion, V. B., Reisner, E., Fremuth, M., Jakupec, M. A., Keppler, B. K., Kukushkin, V. Y. & Pombeiro, A. J. (2003). Inorg. Chem. 42, 6024–6031. Web of Science CSD CrossRef PubMed CAS Google Scholar
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ding, B., Liu, Y.-Y., Huang, Y.-Q., Shi, W., Cheng, P., Liao, D.-Z. & Yan, S.-P. (2009). Cryst. Growth Des. 9, 593–601. Web of Science CSD CrossRef CAS Google Scholar
Li, B. L., Peng, Y. F., Li, B. Z. & Zhang, Y. (2005). Chem. Commun. 18, 2333–2335. Web of Science CSD CrossRef Google Scholar
Meng, X., Song, Y., Hou, H., Han, H., Xiao, B., Fan, Y. & Zhu, Y. (2004). Inorg. Chem. 43, 3528–3536. Web of Science CSD CrossRef PubMed CAS Google Scholar
Peng, Y. F., Ge, H. Y., Li, B. L. & Zhang, Y. (2006). Cryst. Growth Des. 6, 994–998. Web of Science CSD CrossRef CAS Google Scholar
Peng, Y. F., Li, B. Z., Zhou, J. H., Li, B. L. & Zhang, Y. (2004). Chin. J. Struct. Chem. 23, 985–988. CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o537

doi:10.1107/S1600536810002618

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-{4-[(1H-1,2,4-Triazol-1-yl)meth­yl]benz­yl}-1H-1,2,4-triazol-4-ium perchlorate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

1-{4-[(1H-1,2,4-Triazol-1-yl)methyl]benzyl}-1H-1,2,4-triazol-4-ium perchlorate