3-Benzyl­sulfanyl-5-(4-phenyl-1H-1,2,3-triazol-1-ylmeth­yl)-4H-1,2,4-triazol-4-amine

Chu, Q.-Z.; Zhou, H.-R.; Zhang, X.-R.

doi:10.1107/S1600536808023180

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1611

doi:10.1107/S1600536808023180

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3-Benzylsulfanyl-5-(4-phenyl-1H-1,2,3-triazol-1-ylmethyl)-4H-1,2,4-triazol-4-amine

Qing-Zhu Chu,^a Huan-Ran Zhou ^a and Xiao-Ru Zhang ^a ^*

^aCollege of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, 266042 Qingdao, Shandong, People's Republic of China
^*Correspondence e-mail: qustchemistry@126.com

(Received 14 July 2008; accepted 23 July 2008; online 31 July 2008)

The molecule of the title compound, C₁₈H₁₇N₇S, is non-planar, with a dihedral angle of 71.4 (4)° between the two triazole rings, and an angle of 15.5 (3)° between the two phenyl rings. An intramolecular N—H⋯S hydrogen bond forms a five-membered ring.

Related literature

For related literature, see: Allen et al. (1987 ); Barchiesi et al. (2000 ); Colanceska-Ragenovic et al. (2001 ); Kaplancıklı et al. (2008 ); Khanum et al. (2005 ); Rodriguez-Fernandez et al. (2005 ); Zhang et al. (2008 ).

Experimental

Crystal data

C₁₈H₁₇N₇S
M_r = 363.45
Orthorhombic, P n a 2₁
a = 8.0487 (15) Å
b = 5.4689 (10) Å
c = 38.721 (7) Å
V = 1704.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 186.5 (2) K
0.35 × 0.25 × 0.04 mm

Data collection

Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.931, T_max = 0.992
7815 measured reflections
2854 independent reflections
2592 reflections with I > 2σ(I)
R_int = 0.052

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.183
S = 1.20
2854 reflections
235 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.39 e Å⁻³
Absolute structure: Flack (1983 ), with 2854 Freidel pairs
Flack parameter: 0.05 (19)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7B⋯S1	0.86	2.77	3.116 (6)	105

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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, PARST (Nardelli, 1995 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023180/at2597sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808023180/at2597Isup2.hkl

checkCIF report

Comment top

Triazole derivatives exhibit higher antifungal activity against filamentous fungi and yeasts (Barchiesi et al., 2000), and their antibacterial properties have been reported as well (Colanceska-Ragenovic et al., 2001). The biological activities of various 1,2,3-triazole and 1,2,4-triazole derivatives have been extensively studied (Rodriguez-Fernandez et al., 2005; Kaplancıklı et al., 2008; Khanum et al., 2005). As an extension of the work on structure characterization of triazole derivatives, the title compound (I) was synthesized and its structure was characterized by X-ray crystallographic analysis.

In (I) (Fig. 1), all the bond lengths and angles are within normal ranges (Allen et al., 1987). A (N1–N3/C7/C8) triazole ring makes dihedral angles of 11.6 (3) and 25.6 (3)° with B (C1–C6) and C (C13–C18) phenyl rings, respectively, and of 71.4 (4)° with D (N4–N6/C10/C11) triazole ring. In addition, the dihedral angles between B and C, C and D, and B and D are 15.5 (3), 67.7 (3) and 73.7 (3)°, respectively. There exists one intramolecular hydrogen bond, N7—H7B···S1 (Table 1), forming a five-membered ring.

Related literature top

For related literature, see: Allen et al. (1987); Barchiesi et al. (2000); Colanceska-Ragenovic et al. (2001); Kaplancıklı et al. (2008); Khanum et al. (2005); Rodriguez-Fernandez et al. (2005); Zhang et al. (2008).

Experimental top

3-{[4-(4-phenyl)-1H-1,2,3-triazol-1-yl]methyl}-4-amino-5-thiol-1,2,4-triazole (Zhang et al., 2008) (1.00 g, 3.66 mmol) was added to a mixture of 50% NaOH (w/w) 5 ml, water (30 ml) and benzyl bromide (0.87 ml, 7.32 mmol). The mixture was stirred for 5 h. The resulting precipitate was collected by filtration, washed by water and recrystallized from acetone to give compound I (1.09 g, 82.0%). Colourless single crystals suitable for an X-ray diffraction study were obtained by slow evaporation of an ethyl acetate solution.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The structure of the compound (I) showing 50% probability displacement ellipsoids and the atom numbering scheme.
	Fig. 2. A packing diagram of (I), viewed down the c axis.

3-Benzylsulfanyl-5-(4-phenyl-1H-1,2,3-triazol-1-ylmethyl)-4H- 1,2,4-triazol-4-amine top

Crystal data top

C₁₈H₁₇N₇S	F(000) = 760
M_r = 363.45	D_x = 1.416 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1817 reflections
a = 8.0487 (15) Å	θ = 3.2–25.0°
b = 5.4689 (10) Å	µ = 0.21 mm⁻¹
c = 38.721 (7) Å	T = 187 K
V = 1704.4 (5) Å³	Plate, colourless
Z = 4	0.35 × 0.25 × 0.04 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2854 independent reflections
Radiation source: fine-focus sealed tube	2592 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.052
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.0°, θ_min = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −6→5
T_min = 0.931, T_max = 0.992	l = −40→46
7815 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.078	H-atom parameters constrained
wR(F²) = 0.183	w = 1/[σ²(F_o²) + (0.0579P)² + 3.955P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max = 0.002
2854 reflections	Δρ_max = 0.48 e Å⁻³
235 parameters	Δρ_min = −0.39 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 2854 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.05 (19)

Crystal data top

C₁₈H₁₇N₇S	V = 1704.4 (5) Å³
M_r = 363.45	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 8.0487 (15) Å	µ = 0.21 mm⁻¹
b = 5.4689 (10) Å	T = 187 K
c = 38.721 (7) Å	0.35 × 0.25 × 0.04 mm

Data collection top

Siemens SMART 1000 CCD area-detector diffractometer	2854 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2592 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.992	R_int = 0.052
7815 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	H-atom parameters constrained
wR(F²) = 0.183	Δρ_max = 0.48 e Å⁻³
S = 1.20	Δρ_min = −0.39 e Å⁻³
2854 reflections	Absolute structure: Flack (1983), with 2854 Freidel pairs
235 parameters	Absolute structure parameter: 0.05 (19)
1 restraint

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
S1	0.0735 (2)	0.5751 (3)	0.34992 (5)	0.0348 (4)
N5	−0.0030 (7)	0.2276 (10)	0.39829 (15)	0.0349 (13)
C11	0.0723 (7)	0.4329 (11)	0.38974 (17)	0.0284 (14)
N6	0.1621 (6)	0.5157 (9)	0.41739 (14)	0.0299 (12)
C1	−0.0955 (7)	0.3110 (10)	0.60677 (16)	0.0266 (14)
H1A	−0.0314	0.1797	0.5993	0.032*
C7	−0.0485 (7)	0.5171 (11)	0.55000 (16)	0.0245 (14)
N4	0.0366 (7)	0.1806 (11)	0.43251 (16)	0.0398 (15)
C13	−0.0838 (8)	0.4412 (12)	0.29074 (17)	0.0344 (16)
N1	−0.0513 (8)	0.7223 (11)	0.53032 (15)	0.0428 (15)
C3	−0.2600 (7)	0.4969 (12)	0.65095 (18)	0.0305 (14)
H3A	−0.3061	0.4923	0.6730	0.037*
N2	0.0363 (8)	0.6895 (11)	0.50221 (17)	0.0464 (16)
C5	−0.2313 (8)	0.6963 (10)	0.59606 (18)	0.0297 (15)
H5B	−0.2576	0.8261	0.5815	0.036*
C14	−0.0064 (8)	0.2866 (11)	0.26757 (19)	0.0356 (17)
H14A	0.0496	0.1498	0.2758	0.043*
N3	0.0979 (6)	0.4597 (10)	0.50423 (14)	0.0322 (13)
C16	−0.0919 (9)	0.5334 (14)	0.2199 (2)	0.0419 (18)
H16A	−0.0967	0.5634	0.1963	0.050*
N7	0.2650 (7)	0.7185 (10)	0.41686 (15)	0.0423 (15)
H7A	0.3227	0.7555	0.4348	0.051*
H7B	0.2712	0.8075	0.3986	0.051*
C2	−0.1574 (9)	0.3117 (11)	0.63972 (17)	0.0354 (16)
H2B	−0.1299	0.1853	0.6547	0.042*
C4	−0.2935 (8)	0.6914 (11)	0.62878 (17)	0.0302 (15)
H4B	−0.3594	0.8201	0.6365	0.036*
C6	−0.1276 (7)	0.5067 (11)	0.58396 (16)	0.0258 (14)
C17	−0.1648 (8)	0.6881 (11)	0.24299 (18)	0.0334 (16)
H17A	−0.2206	0.8245	0.2346	0.040*
C10	0.1372 (7)	0.3584 (12)	0.44322 (16)	0.0286 (14)
C18	−0.1598 (8)	0.6523 (11)	0.27809 (18)	0.0321 (15)
H18A	−0.2062	0.7662	0.2931	0.038*
C8	0.0472 (7)	0.3493 (11)	0.53312 (16)	0.0271 (14)
H8A	0.0720	0.1910	0.5403	0.033*
C15	−0.0103 (8)	0.3297 (13)	0.2329 (2)	0.0386 (17)
H15A	0.0421	0.2220	0.2178	0.046*
C9	0.2124 (8)	0.3702 (15)	0.47810 (17)	0.0405 (17)
H9A	0.2502	0.2082	0.4846	0.049*
H9B	0.3088	0.4766	0.4774	0.049*
C12	−0.0816 (10)	0.3877 (15)	0.3288 (2)	0.053 (2)
H12A	−0.0565	0.2162	0.3325	0.063*
H12B	−0.1901	0.4213	0.3386	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0327 (8)	0.0356 (9)	0.0361 (9)	−0.0077 (7)	−0.0003 (8)	0.0057 (9)
N5	0.029 (3)	0.035 (3)	0.041 (3)	−0.009 (3)	0.000 (2)	0.007 (3)
C11	0.019 (3)	0.024 (3)	0.043 (4)	0.001 (3)	0.005 (3)	−0.001 (3)
N6	0.027 (3)	0.026 (3)	0.037 (3)	0.001 (2)	0.002 (2)	0.001 (3)
C1	0.018 (3)	0.019 (3)	0.042 (4)	0.004 (3)	−0.004 (3)	0.003 (3)
C7	0.019 (3)	0.017 (3)	0.037 (4)	0.003 (2)	−0.005 (2)	−0.002 (3)
N4	0.033 (3)	0.043 (4)	0.043 (4)	0.004 (3)	0.009 (3)	0.014 (3)
C13	0.032 (4)	0.029 (3)	0.042 (4)	−0.006 (3)	−0.006 (3)	0.008 (3)
N1	0.046 (3)	0.039 (3)	0.043 (4)	0.014 (3)	0.011 (3)	0.011 (3)
C3	0.020 (3)	0.032 (4)	0.040 (4)	−0.006 (3)	0.000 (3)	−0.001 (3)
N2	0.047 (4)	0.037 (4)	0.055 (4)	0.018 (3)	0.011 (3)	0.016 (3)
C5	0.032 (3)	0.010 (3)	0.048 (4)	0.004 (3)	−0.007 (3)	0.002 (2)
C14	0.021 (3)	0.015 (3)	0.071 (5)	0.007 (3)	−0.011 (3)	0.006 (3)
N3	0.016 (2)	0.041 (3)	0.039 (3)	0.011 (2)	0.000 (2)	0.002 (3)
C16	0.036 (4)	0.051 (5)	0.039 (4)	−0.019 (4)	−0.004 (3)	−0.001 (4)
N7	0.042 (3)	0.033 (3)	0.051 (4)	−0.011 (3)	−0.008 (3)	0.006 (3)
C2	0.042 (4)	0.025 (3)	0.040 (4)	−0.005 (3)	−0.002 (3)	0.005 (3)
C4	0.024 (3)	0.023 (3)	0.044 (4)	0.011 (3)	0.001 (3)	−0.004 (3)
C6	0.025 (3)	0.020 (3)	0.032 (4)	−0.008 (3)	−0.007 (3)	0.001 (2)
C17	0.026 (3)	0.018 (3)	0.056 (5)	−0.009 (3)	0.005 (3)	0.001 (3)
C10	0.024 (3)	0.030 (3)	0.031 (4)	0.005 (3)	0.003 (3)	0.004 (3)
C18	0.023 (3)	0.023 (3)	0.050 (4)	0.004 (3)	0.006 (3)	0.000 (3)
C8	0.029 (3)	0.015 (3)	0.037 (4)	0.011 (3)	−0.005 (3)	−0.001 (3)
C15	0.030 (4)	0.034 (4)	0.052 (5)	−0.001 (3)	−0.001 (3)	−0.015 (3)
C9	0.026 (3)	0.060 (5)	0.035 (4)	0.007 (3)	0.007 (3)	−0.001 (4)
C12	0.045 (4)	0.060 (5)	0.053 (5)	−0.034 (4)	−0.008 (4)	0.012 (4)

Geometric parameters (Å, º) top

S1—C11	1.727 (6)	C5—C6	1.411 (9)
S1—C12	1.810 (7)	C5—H5B	0.9300
N5—C11	1.318 (8)	C14—C15	1.365 (10)
N5—N4	1.387 (8)	C14—H14A	0.9300
C11—N6	1.369 (8)	N3—C8	1.335 (8)
N6—C10	1.334 (8)	N3—C9	1.454 (8)
N6—N7	1.385 (7)	C16—C17	1.363 (10)
C1—C2	1.370 (9)	C16—C15	1.386 (10)
C1—C6	1.412 (8)	C16—H16A	0.9300
C1—H1A	0.9300	N7—H7A	0.8600
C7—N1	1.357 (8)	N7—H7B	0.8600
C7—C8	1.365 (8)	C2—H2B	0.9300
C7—C6	1.462 (8)	C4—H4B	0.9300
N4—C10	1.332 (9)	C17—C18	1.374 (9)
C13—C14	1.381 (10)	C17—H17A	0.9300
C13—C18	1.395 (9)	C10—C9	1.481 (9)
C13—C12	1.503 (10)	C18—H18A	0.9300
N1—N2	1.309 (8)	C8—H8A	0.9300
C3—C2	1.377 (9)	C15—H15A	0.9300
C3—C4	1.393 (9)	C9—H9A	0.9700
C3—H3A	0.9300	C9—H9B	0.9700
N2—N3	1.353 (8)	C12—H12A	0.9700
C5—C4	1.362 (9)	C12—H12B	0.9700

C11—S1—C12	98.3 (3)	H7A—N7—H7B	120.0
C11—N5—N4	107.0 (5)	C1—C2—C3	121.0 (6)
N5—C11—N6	109.2 (5)	C1—C2—H2B	119.5
N5—C11—S1	127.6 (5)	C3—C2—H2B	119.5
N6—C11—S1	123.1 (4)	C5—C4—C3	121.2 (6)
C10—N6—C11	107.1 (5)	C5—C4—H4B	119.4
C10—N6—N7	128.1 (6)	C3—C4—H4B	119.4
C11—N6—N7	124.7 (5)	C5—C6—C1	117.2 (6)
C2—C1—C6	120.9 (6)	C5—C6—C7	121.9 (6)
C2—C1—H1A	119.5	C1—C6—C7	120.8 (6)
C6—C1—H1A	119.5	C16—C17—C18	123.2 (7)
N1—C7—C8	107.3 (6)	C16—C17—H17A	118.4
N1—C7—C6	122.0 (5)	C18—C17—H17A	118.4
C8—C7—C6	130.6 (6)	N4—C10—N6	109.2 (6)
C10—N4—N5	107.6 (5)	N4—C10—C9	124.3 (6)
C14—C13—C18	118.4 (6)	N6—C10—C9	126.5 (6)
C14—C13—C12	120.8 (6)	C17—C18—C13	118.6 (6)
C18—C13—C12	120.7 (7)	C17—C18—H18A	120.7
N2—N1—C7	110.1 (5)	C13—C18—H18A	120.7
C2—C3—C4	118.9 (6)	N3—C8—C7	105.6 (5)
C2—C3—H3A	120.6	N3—C8—H8A	127.2
C4—C3—H3A	120.6	C7—C8—H8A	127.2
N1—N2—N3	106.0 (5)	C14—C15—C16	120.3 (7)
C4—C5—C6	120.7 (6)	C14—C15—H15A	119.8
C4—C5—H5B	119.6	C16—C15—H15A	119.8
C6—C5—H5B	119.6	N3—C9—C10	113.0 (5)
C15—C14—C13	121.6 (6)	N3—C9—H9A	109.0
C15—C14—H14A	119.2	C10—C9—H9A	109.0
C13—C14—H14A	119.2	N3—C9—H9B	109.0
C8—N3—N2	110.9 (5)	C10—C9—H9B	109.0
C8—N3—C9	128.7 (5)	H9A—C9—H9B	107.8
N2—N3—C9	120.3 (6)	C13—C12—S1	109.9 (5)
C17—C16—C15	117.8 (7)	C13—C12—H12A	109.7
C17—C16—H16A	121.1	S1—C12—H12A	109.7
C15—C16—H16A	121.1	C13—C12—H12B	109.7
N6—N7—H7A	120.0	S1—C12—H12B	109.7
N6—N7—H7B	120.0	H12A—C12—H12B	108.2

N4—N5—C11—N6	1.3 (7)	N1—C7—C6—C1	−167.2 (6)
N4—N5—C11—S1	177.6 (5)	C8—C7—C6—C1	7.4 (10)
C12—S1—C11—N5	9.0 (7)	C15—C16—C17—C18	0.5 (10)
C12—S1—C11—N6	−175.1 (6)	N5—N4—C10—N6	0.3 (7)
N5—C11—N6—C10	−1.1 (7)	N5—N4—C10—C9	−177.8 (6)
S1—C11—N6—C10	−177.7 (5)	C11—N6—C10—N4	0.5 (7)
N5—C11—N6—N7	175.7 (6)	N7—N6—C10—N4	−176.2 (6)
S1—C11—N6—N7	−0.8 (8)	C11—N6—C10—C9	178.5 (6)
C11—N5—N4—C10	−1.0 (7)	N7—N6—C10—C9	1.8 (10)
C8—C7—N1—N2	0.4 (8)	C16—C17—C18—C13	−3.3 (10)
C6—C7—N1—N2	176.2 (6)	C14—C13—C18—C17	4.6 (9)
C7—N1—N2—N3	−0.7 (8)	C12—C13—C18—C17	−177.3 (6)
C18—C13—C14—C15	−3.3 (10)	N2—N3—C8—C7	−0.6 (7)
C12—C13—C14—C15	178.6 (6)	C9—N3—C8—C7	175.1 (6)
N1—N2—N3—C8	0.8 (7)	N1—C7—C8—N3	0.1 (7)
N1—N2—N3—C9	−175.3 (6)	C6—C7—C8—N3	−175.1 (6)
C6—C1—C2—C3	3.4 (9)	C13—C14—C15—C16	0.5 (10)
C4—C3—C2—C1	−3.2 (9)	C17—C16—C15—C14	0.9 (10)
C6—C5—C4—C3	−1.6 (10)	C8—N3—C9—C10	121.5 (7)
C2—C3—C4—C5	2.3 (10)	N2—N3—C9—C10	−63.1 (8)
C4—C5—C6—C1	1.7 (9)	N4—C10—C9—N3	−79.2 (8)
C4—C5—C6—C7	−175.0 (6)	N6—C10—C9—N3	103.1 (8)
C2—C1—C6—C5	−2.6 (8)	C14—C13—C12—S1	101.0 (7)
C2—C1—C6—C7	174.1 (6)	C18—C13—C12—S1	−77.1 (8)
N1—C7—C6—C5	9.3 (9)	C11—S1—C12—C13	−169.3 (6)
C8—C7—C6—C5	−176.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7B···S1	0.86	2.78	3.116 (6)	105

Experimental details

Crystal data
Chemical formula	C₁₈H₁₇N₇S
M_r	363.45
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	187
a, b, c (Å)	8.0487 (15), 5.4689 (10), 38.721 (7)
V (Å³)	1704.4 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.35 × 0.25 × 0.04

Data collection
Diffractometer	Siemens SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.931, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	7815, 2854, 2592
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.183, 1.20
No. of reflections	2854
No. of parameters	235
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.39
Absolute structure	Flack (1983), with 2854 Freidel pairs
Absolute structure parameter	0.05 (19)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7B···S1	0.86	2.775	3.116 (6)	105.43

Acknowledgements

This project was supported by the Natural Science Foundation of Shandong Province (grant No. Y2006B07).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
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Volume 64| Part 8| August 2008| Page o1611

doi:10.1107/S1600536808023180

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

3-Benzyl­sulfanyl-5-(4-phenyl-1H-1,2,3-triazol-1-ylmeth­yl)-4H-1,2,4-triazol-4-amine

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-Benzylsulfanyl-5-(4-phenyl-1H-1,2,3-triazol-1-ylmethyl)-4H-1,2,4-triazol-4-amine