1-{4-[(1H-1,2,4-Triazol-1-yl)meth-yl]benz-yl}-1H-1,2,4-triazol-4-ium perchlorate.

In the crystal structure of the title compound, C(12)H(13)N(6) (+)·ClO(4) (-), 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 C(2) 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, inter-molecular N-H⋯N hydrogen bonding between the triazole and triazolium rings links the cations into a wave-like supra-molecular chain. Weak inter-molecular 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 = 340.73

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.139

S = 1.09

1436 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.61 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H13N6+·ClO4−	F(000) = 704
Mr = 340.73	Dx = 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

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

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(Fo2) + (0.0491P)2 + 2.663P] where P = (Fo2 + 2Fc2)/3
1436 reflections	(Δ/σ)max < 0.001
120 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

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.

	x	y	z	Uiso*/Ueq	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

	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)

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)

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···O4iv	0.93	2.54	3.445 (12)	164
C3—H3···O2v	0.93	2.55	3.403 (15)	152
C4—H4A···O4vi	0.97	2.46	3.430 (15)	176
C6—H6···N2vi	0.93	2.55	3.256 (4)	133

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⋯O4iv	0.97	2.46	3.430 (15)	176
C6—H6⋯N2iv	0.93	2.55	3.256 (4)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .