Crystal structure of bis­(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate

Qin, Y.-Q.; Xue, J.; Qiao, Y.-B.; Zhang, Z.-F.

doi:10.1107/S1600536814024829

organic compounds

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ISSN: 2056-9890

Volume 70| Part 12| December 2014| Pages o1290-o1291

doi:10.1107/S1600536814024829

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Crystal structure of bis(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate

Yong-Qi Qin,^a ^* Jin-hui Xue,^b Yuan-Biao Qiao ^a and Zi-Feng Zhang ^b

^aLaboratory of Medicinal Chemistry, Lvliang University, Lvliang, Shanxi 033001, People's Republic of China, and ^bDepartment of Chemistry and Chemical Engineering, Lvliang University, Lvliang, Shanxi 033001, People's Republic of China
^*Correspondence e-mail: qinyq2003@163.com

Edited by V. Rybakov, Moscow State University, Russia (Received 23 March 2014; accepted 12 November 2014; online 26 November 2014)

The title compound, 2C₉H₉N₃·HClO₄, was prepared by reaction of 1-benzyl-1H-1,2,4-triazole and HClO₄ in ethanol at room temperature. The asymmetric unit consists of two molecules of 1-benzyl-1H-1,2,4-triazole and one of HClO₄ molecule. The benzene and triazole rings make dihedral angles of 85.45 (8) and 84.76 (8)° in the two molecules. The H-atom position of the perchloric acid molecule is split over two O atoms (real peaks on difference map), with site-occupation factors of 0.5. These H atoms form two classical hydrogen bonds [2.546 (5) and 2.620 (4) Å] with the same N atoms in both molecules. Five intermolecular non-classical C—H⋯O interactions, with C⋯O distances in the range 3.147 (5)–3.483 (5) Å, are found in the crystal structure.

Keywords: crystal structure; 1H-1,2,4-triazole; perchloric acid; antiviral activity.

CCDC reference: 1033730

1. Related literature

For the antiviral activity of triazole derivatives, see: Madan & Taneja (1991 ); Borisova et al. (2007 ) and of polyligand complexes with metals, see: Xu et al. (2004 ). For a related structure, see: Ji et al. (2002 ).

2. Experimental

2.1. Crystal data

2C₉H₉N₃·HClO₄
M_r = 418.84
Monoclinic, P 2₁
a = 5.7173 (10) Å
b = 7.7671 (12) Å
c = 21.955 (4) Å
β = 95.136 (4)°
V = 971.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.25 × 0.23 × 0.20 mm

2.2. Data collection

Bruker SMART CCD diffractometer
9373 measured reflections
3981 independent reflections
2680 reflections with I > 2σ(I)
R_int = 0.050

2.3. Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.137
S = 1.05
3981 reflections
263 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), 873 Friedel pairs
Absolute structure parameter: 0.27 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N6ⁱ	0.82	2.04	2.620 (4)	127
O1—H1⋯N3ⁱⁱ	0.82	1.78	2.546 (5)	154
C10—H10B⋯O4	0.97	2.35	3.282 (5)	160
C9—H9⋯O2ⁱⁱⁱ	0.93	2.52	3.352 (6)	150
C1—H1A⋯O2^iv	0.97	2.56	3.483 (5)	158
C17—H17⋯O4^v	0.93	2.43	3.147 (5)	134
C18—H18⋯O3^vi	0.93	2.44	3.185 (5)	137
Symmetry codes: (i) x-1, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+1]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (v) x+1, y, z; (vi) x, y+1, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; 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

CCDC reference: 1033730

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814024829/rk2425sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814024829/rk2425Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814024829/rk2425Isup3.cml

checkCIF report

Comment top

It is well known, that triazole derivatives possess anti-viral activities (Madan & Taneja, 1991; Borisova et al., 2007). A materials about anti-viral activities of the such polyligand complexes with metals were published Xu et al., 2004. These facts were of a reason for structural study of 1-benzyl-1H-1,2,4-triazole HClO₄ solvate.

In the molecule of the title compound (Fig. 1), bond lengths and angles are generally normal in benzene and 1,2,4-triazole ring (Ji et al., 2002). The torsion angles of C2—C1—N1—C8 and N1—C1—C2—C3 are -108.2 (4)° and 60.3 (5)°, respectively; C11—C10—N4—C17 and N4—C10—C11—C12 are 115.2 (4)° and 124.3 (4)° respectively. The dihedral angle formed by the benzene and the triazole ring is 85.45 (8)° and 84.76 (8)° for first and second molecules respectively.

There are some classical O—H···N and non-classical C—H···O intermolecular interactions stabilize the title crystal structure (Fig. 2).

Related literature top

For the antiviral activity of triazole derivatives, see: Madan & Taneja (1991); Borisova et al. (2007) and of polyligand complexes with metals, see: Xu et al. (2004). For a related structure, see: Ji et al. (2002).

Experimental top

The title compound was prepared by reaction of benzyl chloride (0.05 mol), triazole (0.05 mol), potassium carbonate (0.06 mol) and potassium iodide (0.5 g) in the acetone solution (40 ml) at 333 K for 8 h, filtering, evaporating the solvent, affording the tile compound (6.2 g, yield 78%) by solidification in the etanol solution of HClO₄ (5%, 15 ml). In the reaction, potassium carbonate can powerfully adsorb HCl to promote the reaction and potassium iodide is catalyst. Single crystals of the title compound suitable for X-ray measurements was obtained by recrystallization from ethanol/acetone (v/v = 1:1) at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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 atom numbering scheme. The displacement ellipsoids are drawn at the 40% probability level H atoms are presented as a small spheres of arbitrary radius.

Fig. 2. The packing of the title compound, viewed down the b axis, showing short contact (dashed lines).

Bis(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate top

Crystal data top

2C₉H₉N₃·HClO₄	F(000) = 436
M_r = 418.84	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 5.7173 (10) Å	Cell parameters from 637 reflections
b = 7.7671 (12) Å	θ = 3.2–19.6°
c = 21.955 (4) Å	µ = 0.24 mm⁻¹
β = 95.136 (4)°	T = 296 K
V = 971.0 (3) Å³	Rectangle, colourless
Z = 2	0.25 × 0.23 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2680 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.050
Graphite monochromator	θ_max = 28.1°, θ_min = 2.8°
ϕ and ω scans	h = −7→7
9373 measured reflections	k = −9→9
3981 independent reflections	l = −28→28

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.053	w = 1/[σ²(F_o²) + (0.0604P)² + 0.021P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.137	(Δ/σ)_max < 0.001
S = 1.05	Δρ_max = 0.35 e Å⁻³
3981 reflections	Δρ_min = −0.39 e Å⁻³
263 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.007 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983) parameter determined using 873 quotients
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.27 (9)

Crystal data top

2C₉H₉N₃·HClO₄	V = 971.0 (3) Å³
M_r = 418.84	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 5.7173 (10) Å	µ = 0.24 mm⁻¹
b = 7.7671 (12) Å	T = 296 K
c = 21.955 (4) Å	0.25 × 0.23 × 0.20 mm
β = 95.136 (4)°

Data collection top

Bruker SMART CCD diffractometer	2680 reflections with I > 2σ(I)
9373 measured reflections	R_int = 0.050
3981 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.137	Δρ_max = 0.35 e Å⁻³
S = 1.05	Δρ_min = −0.39 e Å⁻³
3981 reflections	Absolute structure: Flack (1983) parameter determined using 873 quotients
263 parameters	Absolute structure parameter: 0.27 (9)
1 restraint

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	0.22466 (15)	0.25879 (13)	0.75737 (4)	0.0376 (3)
O2	−0.0268 (4)	0.2501 (5)	0.75956 (13)	0.0501 (7)
O3	0.3257 (5)	0.0851 (3)	0.75971 (14)	0.0506 (8)
H3A	0.2975	0.0380	0.7917	0.076*	0.50
O1	0.2712 (5)	0.3307 (4)	0.69478 (12)	0.0520 (8)
H1	0.3440	0.4193	0.7039	0.078*	0.50
O4	0.3397 (5)	0.3708 (4)	0.80363 (14)	0.0579 (9)
N2	0.1586 (5)	0.2466 (5)	0.33197 (15)	0.0446 (8)
C5	0.1887 (8)	0.5483 (7)	0.5465 (2)	0.0544 (12)
H5	0.1552	0.5518	0.5871	0.065*
N3	0.4745 (6)	0.0982 (5)	0.31116 (16)	0.0459 (9)
C9	0.2415 (8)	0.0996 (6)	0.3156 (2)	0.0474 (11)
H9	0.1473	0.0032	0.3076	0.057*
N1	0.3519 (6)	0.3489 (4)	0.33810 (14)	0.0351 (8)
C1	0.3406 (8)	0.5273 (5)	0.35882 (18)	0.0443 (11)
H1A	0.2189	0.5877	0.3336	0.053*
H1B	0.4891	0.5838	0.3539	0.053*
C6	0.0396 (8)	0.6210 (7)	0.5020 (2)	0.0549 (13)
H6	−0.0967	0.6744	0.5125	0.066*
C2	0.2893 (7)	0.5377 (5)	0.42460 (18)	0.0364 (9)
C8	0.5381 (6)	0.2598 (7)	0.32578 (17)	0.0417 (9)
H8	0.6903	0.3026	0.3271	0.050*
C4	0.3899 (8)	0.4693 (6)	0.53045 (19)	0.0507 (12)
H4	0.4927	0.4191	0.5605	0.061*
C7	0.0878 (7)	0.6168 (6)	0.4414 (2)	0.0460 (11)
H7	−0.0161	0.6675	0.4117	0.055*
C3	0.4401 (7)	0.4640 (6)	0.4706 (2)	0.0454 (11)
H3	0.5770	0.4104	0.4606	0.054*
N5	0.7031 (5)	0.7708 (5)	0.83783 (15)	0.0417 (8)
N4	0.8811 (6)	0.6541 (4)	0.84658 (14)	0.0366 (8)
C18	0.7984 (7)	0.9014 (6)	0.81290 (17)	0.0395 (10)
H18	0.7188	1.0027	0.8019	0.047*
C16	0.9431 (7)	0.5756 (6)	0.98327 (19)	0.0420 (10)
H16	1.0821	0.6247	0.9726	0.050*
N6	1.0286 (6)	0.8733 (4)	0.80462 (14)	0.0356 (8)
C11	0.7924 (6)	0.4980 (5)	0.93922 (17)	0.0317 (9)
C12	0.5874 (7)	0.4219 (6)	0.95742 (18)	0.0405 (10)
H12	0.4834	0.3681	0.9284	0.049*
C10	0.8470 (8)	0.4849 (5)	0.87376 (19)	0.0441 (11)
H10A	0.9882	0.4167	0.8716	0.053*
H10B	0.7192	0.4259	0.8503	0.053*
C14	0.6861 (8)	0.5066 (6)	1.0598 (2)	0.0485 (12)
H14	0.6493	0.5113	1.1002	0.058*
C17	1.0749 (7)	0.7164 (5)	0.82694 (18)	0.0357 (10)
H17	1.2192	0.6605	0.8284	0.043*
C15	0.8882 (8)	0.5809 (6)	1.0437 (2)	0.0507 (12)
H15	0.9894	0.6352	1.0732	0.061*
C13	0.5389 (8)	0.4258 (6)	1.01696 (19)	0.0482 (12)
H13	0.4038	0.3727	1.0284	0.058*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0384 (5)	0.0346 (5)	0.0404 (5)	0.0025 (5)	0.0060 (4)	0.0025 (5)
O2	0.0300 (13)	0.0547 (19)	0.0666 (19)	0.0054 (16)	0.0088 (12)	−0.0001 (19)
O3	0.0517 (17)	0.0285 (16)	0.075 (2)	0.0139 (14)	0.0271 (15)	0.0174 (15)
O1	0.078 (2)	0.0441 (18)	0.0338 (16)	−0.0108 (16)	0.0065 (15)	0.0126 (13)
O4	0.0575 (19)	0.065 (2)	0.0497 (19)	−0.0129 (17)	−0.0052 (15)	−0.0157 (17)
N2	0.0429 (17)	0.039 (2)	0.052 (2)	0.000 (2)	0.0037 (15)	−0.003 (2)
C5	0.063 (3)	0.053 (3)	0.048 (3)	−0.005 (3)	0.010 (2)	−0.010 (2)
N3	0.057 (2)	0.045 (2)	0.035 (2)	−0.0044 (19)	0.0028 (17)	−0.0077 (17)
C9	0.050 (3)	0.044 (3)	0.047 (3)	−0.010 (2)	−0.005 (2)	−0.008 (2)
N1	0.0440 (19)	0.033 (2)	0.0289 (17)	0.0003 (16)	0.0082 (15)	−0.0037 (15)
C1	0.057 (3)	0.031 (3)	0.045 (3)	−0.001 (2)	0.007 (2)	0.007 (2)
C6	0.042 (3)	0.066 (4)	0.059 (3)	0.001 (2)	0.014 (2)	−0.014 (3)
C2	0.040 (2)	0.029 (2)	0.040 (2)	−0.0019 (18)	0.0032 (18)	−0.0044 (19)
C8	0.041 (2)	0.045 (3)	0.040 (2)	−0.009 (3)	0.0093 (17)	−0.002 (3)
C4	0.065 (3)	0.046 (3)	0.039 (3)	0.003 (2)	−0.011 (2)	−0.003 (2)
C7	0.048 (3)	0.041 (3)	0.048 (3)	0.008 (2)	0.001 (2)	−0.001 (2)
C3	0.043 (2)	0.043 (3)	0.050 (3)	0.009 (2)	0.004 (2)	−0.010 (2)
N5	0.0370 (16)	0.040 (2)	0.049 (2)	0.0052 (18)	0.0065 (14)	0.003 (2)
N4	0.042 (2)	0.033 (2)	0.0354 (18)	−0.0029 (15)	0.0076 (16)	0.0000 (16)
C18	0.044 (2)	0.040 (3)	0.034 (2)	0.007 (2)	0.0028 (18)	0.005 (2)
C16	0.040 (2)	0.039 (2)	0.047 (3)	−0.0060 (19)	0.0015 (19)	0.000 (2)
N6	0.0432 (19)	0.033 (2)	0.0307 (18)	0.0002 (16)	0.0060 (15)	−0.0007 (16)
C11	0.039 (2)	0.022 (2)	0.034 (2)	0.0028 (17)	0.0034 (17)	0.0023 (17)
C12	0.040 (2)	0.045 (3)	0.036 (2)	−0.0062 (19)	0.0009 (18)	0.007 (2)
C10	0.053 (3)	0.033 (2)	0.049 (3)	−0.002 (2)	0.016 (2)	0.008 (2)
C14	0.060 (3)	0.047 (3)	0.040 (2)	0.014 (2)	0.008 (2)	0.014 (2)
C17	0.037 (2)	0.031 (3)	0.039 (2)	−0.0017 (18)	0.0049 (17)	0.0010 (17)
C15	0.062 (3)	0.043 (3)	0.044 (3)	−0.001 (2)	−0.012 (2)	0.002 (2)
C13	0.046 (3)	0.058 (3)	0.043 (3)	−0.005 (2)	0.012 (2)	0.013 (2)

Geometric parameters (Å, º) top

Cl1—O2	1.444 (2)	C4—H4	0.9300
Cl1—O4	1.449 (3)	C7—H7	0.9300
Cl1—O3	1.466 (3)	C3—H3	0.9300
Cl1—O1	1.529 (3)	N5—C18	1.295 (5)
O3—H3A	0.8200	N5—N4	1.363 (4)
O1—H1	0.8200	N4—C17	1.317 (5)
N2—C9	1.299 (6)	N4—C10	1.464 (5)
N2—N1	1.358 (4)	C18—N6	1.362 (5)
C5—C6	1.359 (7)	C18—H18	0.9300
C5—C4	1.377 (6)	C16—C11	1.375 (5)
C5—H5	0.9300	C16—C15	1.390 (6)
N3—C8	1.338 (6)	C16—H16	0.9300
N3—C9	1.345 (5)	N6—C17	1.331 (5)
C9—H9	0.9300	C11—C12	1.402 (5)
N1—C8	1.318 (5)	C11—C10	1.501 (5)
N1—C1	1.462 (5)	C12—C13	1.361 (5)
C1—C2	1.501 (5)	C12—H12	0.9300
C1—H1A	0.9700	C10—H10A	0.9700
C1—H1B	0.9700	C10—H10B	0.9700
C6—C7	1.384 (6)	C14—C13	1.359 (6)
C6—H6	0.9300	C14—C15	1.367 (6)
C2—C7	1.384 (5)	C14—H14	0.9300
C2—C3	1.391 (6)	C17—H17	0.9300
C8—H8	0.9300	C15—H15	0.9300
C4—C3	1.370 (6)	C13—H13	0.9300

O2—Cl1—O4	113.29 (19)	C2—C7—H7	119.7
O2—Cl1—O3	110.2 (2)	C4—C3—C2	121.0 (4)
O4—Cl1—O3	112.0 (2)	C4—C3—H3	119.5
O2—Cl1—O1	107.50 (18)	C2—C3—H3	119.5
O4—Cl1—O1	107.82 (19)	C18—N5—N4	104.1 (3)
O3—Cl1—O1	105.54 (17)	C17—N4—N5	110.4 (3)
Cl1—O3—H3A	109.5	C17—N4—C10	127.6 (3)
Cl1—O1—H1	102.2	N5—N4—C10	122.0 (3)
C9—N2—N1	103.2 (3)	N5—C18—N6	112.3 (4)
C6—C5—C4	119.1 (4)	N5—C18—H18	123.9
C6—C5—H5	120.4	N6—C18—H18	123.9
C4—C5—H5	120.4	C11—C16—C15	120.2 (4)
C8—N3—C9	103.0 (4)	C11—C16—H16	119.9
N2—C9—N3	114.6 (4)	C15—C16—H16	119.9
N2—C9—H9	122.7	C17—N6—C18	105.1 (4)
N3—C9—H9	122.7	C16—C11—C12	118.1 (4)
C8—N1—N2	109.7 (3)	C16—C11—C10	122.2 (4)
C8—N1—C1	128.4 (4)	C12—C11—C10	119.7 (4)
N2—N1—C1	121.8 (3)	C13—C12—C11	120.8 (4)
N1—C1—C2	111.6 (3)	C13—C12—H12	119.6
N1—C1—H1A	109.3	C11—C12—H12	119.6
C2—C1—H1A	109.3	N4—C10—C11	112.1 (3)
N1—C1—H1B	109.3	N4—C10—H10A	109.2
C2—C1—H1B	109.3	C11—C10—H10A	109.2
H1A—C1—H1B	108.0	N4—C10—H10B	109.2
C5—C6—C7	120.9 (4)	C11—C10—H10B	109.2
C5—C6—H6	119.5	H10A—C10—H10B	107.9
C7—C6—H6	119.5	C13—C14—C15	120.1 (4)
C7—C2—C3	117.7 (4)	C13—C14—H14	120.0
C7—C2—C1	121.3 (4)	C15—C14—H14	120.0
C3—C2—C1	121.0 (4)	N4—C17—N6	108.1 (3)
N1—C8—N3	109.6 (3)	N4—C17—H17	125.9
N1—C8—H8	125.2	N6—C17—H17	125.9
N3—C8—H8	125.2	C14—C15—C16	120.2 (4)
C3—C4—C5	120.6 (4)	C14—C15—H15	119.9
C3—C4—H4	119.7	C16—C15—H15	119.9
C5—C4—H4	119.7	C14—C13—C12	120.6 (4)
C6—C7—C2	120.6 (4)	C14—C13—H13	119.7
C6—C7—H7	119.7	C12—C13—H13	119.7

N1—N2—C9—N3	0.6 (5)	C18—N5—N4—C17	−0.1 (4)
C8—N3—C9—N2	−0.5 (5)	C18—N5—N4—C10	−179.5 (3)
C9—N2—N1—C8	−0.4 (4)	N4—N5—C18—N6	0.7 (4)
C9—N2—N1—C1	−177.4 (4)	N5—C18—N6—C17	−1.0 (4)
C8—N1—C1—C2	−108.2 (4)	C15—C16—C11—C12	−1.5 (6)
N2—N1—C1—C2	68.1 (5)	C15—C16—C11—C10	−178.3 (4)
C4—C5—C6—C7	−0.1 (8)	C16—C11—C12—C13	0.4 (6)
N1—C1—C2—C7	−118.1 (4)	C10—C11—C12—C13	177.2 (4)
N1—C1—C2—C3	60.3 (5)	C17—N4—C10—C11	115.2 (4)
N2—N1—C8—N3	0.2 (4)	N5—N4—C10—C11	−65.5 (5)
C1—N1—C8—N3	176.9 (4)	C16—C11—C10—N4	−58.9 (5)
C9—N3—C8—N1	0.2 (5)	C12—C11—C10—N4	124.3 (4)
C6—C5—C4—C3	0.1 (8)	N5—N4—C17—N6	−0.5 (4)
C5—C6—C7—C2	0.2 (7)	C10—N4—C17—N6	178.9 (4)
C3—C2—C7—C6	−0.2 (6)	C18—N6—C17—N4	0.8 (4)
C1—C2—C7—C6	178.2 (4)	C13—C14—C15—C16	0.6 (7)
C5—C4—C3—C2	−0.2 (7)	C11—C16—C15—C14	1.0 (6)
C7—C2—C3—C4	0.2 (6)	C15—C14—C13—C12	−1.8 (7)
C1—C2—C3—C4	−178.2 (4)	C11—C12—C13—C14	1.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N6ⁱ	0.82	2.04	2.620 (4)	127
O1—H1···N3ⁱⁱ	0.82	1.78	2.546 (5)	154
C10—H10B···O4	0.97	2.35	3.282 (5)	160
C9—H9···O2ⁱⁱⁱ	0.93	2.52	3.352 (6)	150
C1—H1A···O2^iv	0.97	2.56	3.483 (5)	158
C17—H17···O4^v	0.93	2.43	3.147 (5)	134
C18—H18···O3^vi	0.93	2.44	3.185 (5)	137

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N6ⁱ	0.82	2.04	2.620 (4)	127.4
O1—H1···N3ⁱⁱ	0.82	1.78	2.546 (5)	154.1
C10—H10B···O4	0.97	2.35	3.282 (5)	159.7
C9—H9···O2ⁱⁱⁱ	0.93	2.52	3.352 (6)	149.7
C1—H1A···O2^iv	0.97	2.56	3.483 (5)	157.9
C17—H17···O4^v	0.93	2.43	3.147 (5)	133.9
C18—H18···O3^vi	0.93	2.44	3.185 (5)	137.2

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

Acknowledgements

The authors thank the Colleges and Universities Technology Project of Shanxi Province (20121033), and the Natural Science Fund of Lvliang University (ZRXN201206 and ZRXN201210).

References

Borisova, N. E., Reshetova, M. D. & Ustynyuk, Yu. A. (2007). Chem. Rev. 107, 46–79. Web of Science CrossRef PubMed CAS Google Scholar
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Volume 70| Part 12| December 2014| Pages o1290-o1291

doi:10.1107/S1600536814024829

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

Crystal structure of bis­­(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of bis(1-benzyl-1H-1,2,4-triazole) perchloric acid monosolvate