Literature DB >> 21203304

3-Benzyl-sulfanyl-5-(4-phenyl-1H-1,2,3-triazol-1-ylmeth-yl)-4H-1,2,4-triazol-4-amine.

Qing-Zhu Chu1, Huan-Ran Zhou, Xiao-Ru Zhang.   

Abstract

The mol-ecule of the title compound, C(18)H(17)N(7)S, 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 intra-molecular N-H⋯S hydrogen bond forms a five-membered ring.

Entities:  

Year:  2008        PMID： 21203304      PMCID： PMC2962172          DOI： 10.1107/S1600536808023180

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


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 = 363.45 Orthorhombic, 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[F 2 > 2σ(F 2)] = 0.078 wR(F 2) = 0.183 S = 1.20 2854 reflections 235 parameters 1 restraint H-atom parameters constrained Δρmax = 0.48 e Å−3 Δρmin = −0.39 e Å−3 Absolute structure: Flack (1983 ▶), with 2854 Freidel pairs Flack parameter: 0.05 (19) 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 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808023180/at2597sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023180/at2597Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C18H17N7SF000 = 760
Mr = 363.45Dx = 1.416 Mg m−3
Orthorhombic, Pna21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1817 reflections
a = 8.0487 (15) Åθ = 3.2–25.0º
b = 5.4689 (10) ŵ = 0.21 mm−1
c = 38.721 (7) ÅT = 186.5 (2) K
V = 1704.4 (5) Å3Plate, colourless
Z = 40.35 × 0.25 × 0.04 mm
Siemens SMART 1000 CCD area-detector diffractometer2854 independent reflections
Radiation source: fine-focus sealed tube2592 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.052
Detector resolution: 8.33 pixels mm-1θmax = 25.0º
T = 293(2) Kθmin = 2.1º
ω scansh = −9→9
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)k = −6→5
Tmin = 0.931, Tmax = 0.992l = −40→46
7815 measured reflections
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.078  w = 1/[σ2(Fo2) + (0.0579P)2 + 3.955P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.183(Δ/σ)max = 0.002
S = 1.20Δρmax = 0.48 e Å−3
2854 reflectionsΔρmin = −0.39 e Å−3
235 parametersExtinction correction: none
1 restraintAbsolute structure: Flack (1983), with 2854 Freidel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.05 (19)
Secondary atom site location: difference Fourier map
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.
xyzUiso*/Ueq
S10.0735 (2)0.5751 (3)0.34992 (5)0.0348 (4)
N5−0.0030 (7)0.2276 (10)0.39829 (15)0.0349 (13)
C110.0723 (7)0.4329 (11)0.38974 (17)0.0284 (14)
N60.1621 (6)0.5157 (9)0.41739 (14)0.0299 (12)
C1−0.0955 (7)0.3110 (10)0.60677 (16)0.0266 (14)
H1A−0.03140.17970.59930.032*
C7−0.0485 (7)0.5171 (11)0.55000 (16)0.0245 (14)
N40.0366 (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−0.30610.49230.67300.037*
N20.0363 (8)0.6895 (11)0.50221 (17)0.0464 (16)
C5−0.2313 (8)0.6963 (10)0.59606 (18)0.0297 (15)
H5B−0.25760.82610.58150.036*
C14−0.0064 (8)0.2866 (11)0.26757 (19)0.0356 (17)
H14A0.04960.14980.27580.043*
N30.0979 (6)0.4597 (10)0.50423 (14)0.0322 (13)
C16−0.0919 (9)0.5334 (14)0.2199 (2)0.0419 (18)
H16A−0.09670.56340.19630.050*
N70.2650 (7)0.7185 (10)0.41686 (15)0.0423 (15)
H7A0.32270.75550.43480.051*
H7B0.27120.80750.39860.051*
C2−0.1574 (9)0.3117 (11)0.63972 (17)0.0354 (16)
H2B−0.12990.18530.65470.042*
C4−0.2935 (8)0.6914 (11)0.62878 (17)0.0302 (15)
H4B−0.35940.82010.63650.036*
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−0.22060.82450.23460.040*
C100.1372 (7)0.3584 (12)0.44322 (16)0.0286 (14)
C18−0.1598 (8)0.6523 (11)0.27809 (18)0.0321 (15)
H18A−0.20620.76620.29310.038*
C80.0472 (7)0.3493 (11)0.53312 (16)0.0271 (14)
H8A0.07200.19100.54030.033*
C15−0.0103 (8)0.3297 (13)0.2329 (2)0.0386 (17)
H15A0.04210.22200.21780.046*
C90.2124 (8)0.3702 (15)0.47810 (17)0.0405 (17)
H9A0.25020.20820.48460.049*
H9B0.30880.47660.47740.049*
C12−0.0816 (10)0.3877 (15)0.3288 (2)0.053 (2)
H12A−0.05650.21620.33250.063*
H12B−0.19010.42130.33860.063*
U11U22U33U12U13U23
S10.0327 (8)0.0356 (9)0.0361 (9)−0.0077 (7)−0.0003 (8)0.0057 (9)
N50.029 (3)0.035 (3)0.041 (3)−0.009 (3)0.000 (2)0.007 (3)
C110.019 (3)0.024 (3)0.043 (4)0.001 (3)0.005 (3)−0.001 (3)
N60.027 (3)0.026 (3)0.037 (3)0.001 (2)0.002 (2)0.001 (3)
C10.018 (3)0.019 (3)0.042 (4)0.004 (3)−0.004 (3)0.003 (3)
C70.019 (3)0.017 (3)0.037 (4)0.003 (2)−0.005 (2)−0.002 (3)
N40.033 (3)0.043 (4)0.043 (4)0.004 (3)0.009 (3)0.014 (3)
C130.032 (4)0.029 (3)0.042 (4)−0.006 (3)−0.006 (3)0.008 (3)
N10.046 (3)0.039 (3)0.043 (4)0.014 (3)0.011 (3)0.011 (3)
C30.020 (3)0.032 (4)0.040 (4)−0.006 (3)0.000 (3)−0.001 (3)
N20.047 (4)0.037 (4)0.055 (4)0.018 (3)0.011 (3)0.016 (3)
C50.032 (3)0.010 (3)0.048 (4)0.004 (3)−0.007 (3)0.002 (2)
C140.021 (3)0.015 (3)0.071 (5)0.007 (3)−0.011 (3)0.006 (3)
N30.016 (2)0.041 (3)0.039 (3)0.011 (2)0.000 (2)0.002 (3)
C160.036 (4)0.051 (5)0.039 (4)−0.019 (4)−0.004 (3)−0.001 (4)
N70.042 (3)0.033 (3)0.051 (4)−0.011 (3)−0.008 (3)0.006 (3)
C20.042 (4)0.025 (3)0.040 (4)−0.005 (3)−0.002 (3)0.005 (3)
C40.024 (3)0.023 (3)0.044 (4)0.011 (3)0.001 (3)−0.004 (3)
C60.025 (3)0.020 (3)0.032 (4)−0.008 (3)−0.007 (3)0.001 (2)
C170.026 (3)0.018 (3)0.056 (5)−0.009 (3)0.005 (3)0.001 (3)
C100.024 (3)0.030 (3)0.031 (4)0.005 (3)0.003 (3)0.004 (3)
C180.023 (3)0.023 (3)0.050 (4)0.004 (3)0.006 (3)0.000 (3)
C80.029 (3)0.015 (3)0.037 (4)0.011 (3)−0.005 (3)−0.001 (3)
C150.030 (4)0.034 (4)0.052 (5)−0.001 (3)−0.001 (3)−0.015 (3)
C90.026 (3)0.060 (5)0.035 (4)0.007 (3)0.007 (3)−0.001 (4)
C120.045 (4)0.060 (5)0.053 (5)−0.034 (4)−0.008 (4)0.012 (4)
S1—C111.727 (6)C5—C61.411 (9)
S1—C121.810 (7)C5—H5B0.9300
N5—C111.318 (8)C14—C151.365 (10)
N5—N41.387 (8)C14—H14A0.9300
C11—N61.369 (8)N3—C81.335 (8)
N6—C101.334 (8)N3—C91.454 (8)
N6—N71.385 (7)C16—C171.363 (10)
C1—C21.370 (9)C16—C151.386 (10)
C1—C61.412 (8)C16—H16A0.9300
C1—H1A0.9300N7—H7A0.8600
C7—N11.357 (8)N7—H7B0.8600
C7—C81.365 (8)C2—H2B0.9300
C7—C61.462 (8)C4—H4B0.9300
N4—C101.332 (9)C17—C181.374 (9)
C13—C141.381 (10)C17—H17A0.9300
C13—C181.395 (9)C10—C91.481 (9)
C13—C121.503 (10)C18—H18A0.9300
N1—N21.309 (8)C8—H8A0.9300
C3—C21.377 (9)C15—H15A0.9300
C3—C41.393 (9)C9—H9A0.9700
C3—H3A0.9300C9—H9B0.9700
N2—N31.353 (8)C12—H12A0.9700
C5—C41.362 (9)C12—H12B0.9700
C11—S1—C1298.3 (3)H7A—N7—H7B120.0
C11—N5—N4107.0 (5)C1—C2—C3121.0 (6)
N5—C11—N6109.2 (5)C1—C2—H2B119.5
N5—C11—S1127.6 (5)C3—C2—H2B119.5
N6—C11—S1123.1 (4)C5—C4—C3121.2 (6)
C10—N6—C11107.1 (5)C5—C4—H4B119.4
C10—N6—N7128.1 (6)C3—C4—H4B119.4
C11—N6—N7124.7 (5)C5—C6—C1117.2 (6)
C2—C1—C6120.9 (6)C5—C6—C7121.9 (6)
C2—C1—H1A119.5C1—C6—C7120.8 (6)
C6—C1—H1A119.5C16—C17—C18123.2 (7)
N1—C7—C8107.3 (6)C16—C17—H17A118.4
N1—C7—C6122.0 (5)C18—C17—H17A118.4
C8—C7—C6130.6 (6)N4—C10—N6109.2 (6)
C10—N4—N5107.6 (5)N4—C10—C9124.3 (6)
C14—C13—C18118.4 (6)N6—C10—C9126.5 (6)
C14—C13—C12120.8 (6)C17—C18—C13118.6 (6)
C18—C13—C12120.7 (7)C17—C18—H18A120.7
N2—N1—C7110.1 (5)C13—C18—H18A120.7
C2—C3—C4118.9 (6)N3—C8—C7105.6 (5)
C2—C3—H3A120.6N3—C8—H8A127.2
C4—C3—H3A120.6C7—C8—H8A127.2
N1—N2—N3106.0 (5)C14—C15—C16120.3 (7)
C4—C5—C6120.7 (6)C14—C15—H15A119.8
C4—C5—H5B119.6C16—C15—H15A119.8
C6—C5—H5B119.6N3—C9—C10113.0 (5)
C15—C14—C13121.6 (6)N3—C9—H9A109.0
C15—C14—H14A119.2C10—C9—H9A109.0
C13—C14—H14A119.2N3—C9—H9B109.0
C8—N3—N2110.9 (5)C10—C9—H9B109.0
C8—N3—C9128.7 (5)H9A—C9—H9B107.8
N2—N3—C9120.3 (6)C13—C12—S1109.9 (5)
C17—C16—C15117.8 (7)C13—C12—H12A109.7
C17—C16—H16A121.1S1—C12—H12A109.7
C15—C16—H16A121.1C13—C12—H12B109.7
N6—N7—H7A120.0S1—C12—H12B109.7
N6—N7—H7B120.0H12A—C12—H12B108.2
N4—N5—C11—N61.3 (7)N1—C7—C6—C1−167.2 (6)
N4—N5—C11—S1177.6 (5)C8—C7—C6—C17.4 (10)
C12—S1—C11—N59.0 (7)C15—C16—C17—C180.5 (10)
C12—S1—C11—N6−175.1 (6)N5—N4—C10—N60.3 (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—N40.5 (7)
N5—C11—N6—N7175.7 (6)N7—N6—C10—N4−176.2 (6)
S1—C11—N6—N7−0.8 (8)C11—N6—C10—C9178.5 (6)
C11—N5—N4—C10−1.0 (7)N7—N6—C10—C91.8 (10)
C8—C7—N1—N20.4 (8)C16—C17—C18—C13−3.3 (10)
C6—C7—N1—N2176.2 (6)C14—C13—C18—C174.6 (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—C15178.6 (6)C9—N3—C8—C7175.1 (6)
N1—N2—N3—C80.8 (7)N1—C7—C8—N30.1 (7)
N1—N2—N3—C9−175.3 (6)C6—C7—C8—N3−175.1 (6)
C6—C1—C2—C33.4 (9)C13—C14—C15—C160.5 (10)
C4—C3—C2—C1−3.2 (9)C17—C16—C15—C140.9 (10)
C6—C5—C4—C3−1.6 (10)C8—N3—C9—C10121.5 (7)
C2—C3—C4—C52.3 (10)N2—N3—C9—C10−63.1 (8)
C4—C5—C6—C11.7 (9)N4—C10—C9—N3−79.2 (8)
C4—C5—C6—C7−175.0 (6)N6—C10—C9—N3103.1 (8)
C2—C1—C6—C5−2.6 (8)C14—C13—C12—S1101.0 (7)
C2—C1—C6—C7174.1 (6)C18—C13—C12—S1−77.1 (8)
N1—C7—C6—C59.3 (9)C11—S1—C12—C13−169.3 (6)
C8—C7—C6—C5−176.0 (6)
D—H···AD—HH···AD···AD—H···A
N7—H7B···S10.862.783.116 (6)105
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N7—H7B⋯S10.862.773.116 (6)105
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