Literature DB >> 25553052

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

Yong-Qi Qin¹, Jin-Hui Xue², Yuan-Biao Qiao¹, Zi-Feng Zhang².

Abstract

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 mol-ecules of 1-benzyl-1H-1,2,4-triazole and one of HClO4 mol-ecule. The benzene and triazole rings make dihedral angles of 85.45 (8) and 84.76 (8)° in the two mol-ecules. The H-atom position of the perchloric acid mol-ecule 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 mol-ecules. Five inter-molecular non-classical C-H⋯O inter-actions, with C⋯O distances in the range 3.147 (5)-3.483 (5) Å, are found in the crystal structure.

Entities: CellLine Chemical Disease Species

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

Year: 2014 PMID： 25553052 PMCID： PMC4257456 DOI： 10.1107/S1600536814024829

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 ▶).

Experimental

Crystal data

2C9H9N3·HClO4 M = 418.84 Monoclinic, 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

Data collection

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

Refinement

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

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. Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814024829/rk2425sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814024829/rk2425Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814024829/rk2425Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814024829/rk2425fig1.tif 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. Click here for additional data file. b . DOI: 10.1107/S1600536814024829/rk2425fig2.tif The packing of the title compound, viewed down the b axis, showing short contact (dashed lines). CCDC reference: 1033730 Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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 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)

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.

	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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O3H3AN6ⁱ	0.82	2.04	2.620(4)	127
O1H1N3ⁱⁱ	0.82	1.78	2.546(5)	154
C10H10BO4	0.97	2.35	3.282(5)	160
C9H9O2ⁱⁱⁱ	0.93	2.52	3.352(6)	150
C1H1AO2^iv	0.97	2.56	3.483(5)	158
C17H17O4^v	0.93	2.43	3.147(5)	134
C18H18O3^vi	0.93	2.44	3.185(5)	137

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

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