Literature DB >> 21581689

3-Benzamidomethyl-4-[(E)-2-chloro-benzyl-ideneamino]-1H-1,2,4-triazole-5(4H)-thione.

Hoong-Kun Fun, Samuel Robinson Jebas, Jyothi N Rao, B Kalluraya.   

Abstract

In the title compound, C(17)H(14)ClN(5)OS, the dihedral angles formed by the two benzene rings with the triazole ring are 66.88 (3) and 19.16 (3)°, and the benzene rings are inclined to each other with a dihedral angle of 78.40 (3)°. Inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the (100) planes, and centrosymmetric π-π stacking inter-actions [centroid-centroid distance = 3.7717 (5) Å] are formed between benzene rings in neighbouring layers.

Entities:  

Year:  2008        PMID： 21581689      PMCID： PMC2967963          DOI： 10.1107/S1600536808040361

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


Related literature

For pharmaceutical and other applications of triazole compounds, see: Almasirad et al. (2004 ▶); Al-Soud et al. (2003 ▶); Amir & Shikha (2004 ▶); Kalluraya et al. (1996 ▶); Kawashima et al. (1987 ▶).

Experimental

Crystal data

C17H14ClN5OS M = 371.84 Monoclinic, a = 17.0185 (6) Å b = 8.0905 (3) Å c = 12.8292 (5) Å β = 105.962 (2)° V = 1698.32 (11) Å3 Z = 4 Mo Kα radiation μ = 0.36 mm−1 T = 100.0 (1) K 0.70 × 0.48 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.785, T max = 0.949 57891 measured reflections 7463 independent reflections 6349 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.033 wR(F 2) = 0.098 S = 1.09 7463 reflections 234 parameters 2 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.59 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040361/bi2320sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808040361/bi2320Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H14ClN5OSF(000) = 768
Mr = 371.84Dx = 1.454 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9004 reflections
a = 17.0185 (6) Åθ = 2.6–26.3°
b = 8.0905 (3) ŵ = 0.36 mm−1
c = 12.8292 (5) ÅT = 100 K
β = 105.962 (2)°Plate, colourless
V = 1698.32 (11) Å30.70 × 0.48 × 0.15 mm
Z = 4
Bruker SMART APEXII CCD diffractometer7463 independent reflections
Radiation source: fine-focus sealed tube6349 reflections with I > 2σ(I)
graphiteRint = 0.025
φ and ω scansθmax = 35.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −27→27
Tmin = 0.785, Tmax = 0.949k = −12→13
57891 measured reflectionsl = −20→20
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.0502P)2 + 0.4785P] where P = (Fo2 + 2Fc2)/3
7463 reflections(Δ/σ)max = 0.004
234 parametersΔρmax = 0.59 e Å−3
2 restraintsΔρmin = −0.23 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.
xyzUiso*/Ueq
Cl11.007210 (13)1.03657 (3)0.261198 (17)0.02066 (5)
S10.757666 (14)1.12198 (3)0.021681 (19)0.02205 (6)
O10.52774 (4)1.20878 (8)0.36983 (5)0.01823 (12)
N10.52114 (5)0.94734 (9)0.30979 (6)0.01683 (13)
N20.56478 (5)1.09220 (10)0.13014 (6)0.01817 (13)
N30.60840 (5)1.13484 (10)0.05794 (6)0.01859 (14)
N40.69550 (4)1.02508 (9)0.19194 (6)0.01486 (12)
N50.75857 (4)0.95136 (10)0.26923 (6)0.01636 (13)
C10.37543 (6)1.16562 (13)0.41825 (8)0.02102 (16)
H1A0.41291.23330.46590.025*
C20.29456 (7)1.16030 (15)0.42187 (9)0.0288 (2)
H2A0.27791.22320.47260.035*
C30.23860 (7)1.06069 (16)0.34943 (11)0.0332 (3)
H3A0.18461.05690.35220.040*
C40.26273 (6)0.96688 (15)0.27305 (10)0.0308 (2)
H4A0.22470.90190.22410.037*
C50.34392 (6)0.96984 (12)0.26950 (8)0.02199 (17)
H5A0.36030.90640.21880.026*
C60.40030 (5)1.06870 (11)0.34268 (7)0.01574 (14)
C70.48744 (5)1.07999 (10)0.34185 (6)0.01337 (13)
C80.60617 (5)0.94817 (11)0.30987 (7)0.01689 (14)
H8A0.62630.83540.31620.020*
H8B0.63761.00900.37270.020*
C90.61919 (5)1.02410 (10)0.20985 (7)0.01548 (14)
C100.68828 (5)1.09511 (11)0.09059 (7)0.01650 (14)
C110.83182 (5)0.96240 (11)0.26128 (7)0.01659 (14)
H11A0.84361.02040.20480.020*
C120.89642 (5)0.87989 (10)0.34477 (6)0.01453 (13)
C130.97907 (5)0.90723 (10)0.35310 (6)0.01472 (13)
C141.04079 (5)0.83357 (11)0.43414 (7)0.01758 (15)
H14A1.09540.85400.43870.021*
C151.01981 (6)0.72926 (11)0.50811 (7)0.01963 (16)
H15A1.06060.68040.56300.024*
C160.93781 (6)0.69731 (12)0.50042 (7)0.02018 (16)
H16A0.92400.62640.54970.024*
C170.87707 (5)0.77125 (11)0.41949 (7)0.01766 (14)
H17A0.82260.74870.41450.021*
H1N30.5848 (9)1.1788 (19)−0.0026 (9)0.034 (4)*
H1N10.4932 (9)0.8627 (15)0.2855 (13)0.040 (4)*
U11U22U33U12U13U23
Cl10.01679 (9)0.02638 (11)0.01858 (9)−0.00361 (7)0.00446 (7)0.00349 (7)
S10.01723 (10)0.03144 (12)0.01831 (10)0.00069 (8)0.00629 (7)0.00525 (8)
O10.0181 (3)0.0162 (3)0.0190 (3)−0.0035 (2)0.0027 (2)−0.0028 (2)
N10.0142 (3)0.0155 (3)0.0217 (3)−0.0019 (2)0.0065 (2)−0.0035 (2)
N20.0139 (3)0.0220 (3)0.0183 (3)0.0027 (3)0.0040 (2)0.0024 (3)
N30.0147 (3)0.0234 (3)0.0168 (3)0.0032 (3)0.0030 (2)0.0044 (3)
N40.0115 (3)0.0184 (3)0.0143 (3)0.0024 (2)0.0029 (2)0.0018 (2)
N50.0130 (3)0.0202 (3)0.0147 (3)0.0035 (2)0.0020 (2)0.0013 (2)
C10.0211 (4)0.0247 (4)0.0198 (4)0.0061 (3)0.0098 (3)0.0049 (3)
C20.0242 (5)0.0374 (5)0.0302 (5)0.0127 (4)0.0163 (4)0.0145 (4)
C30.0160 (4)0.0428 (6)0.0430 (6)0.0060 (4)0.0117 (4)0.0218 (5)
C40.0146 (4)0.0349 (6)0.0396 (6)−0.0037 (4)0.0015 (4)0.0115 (4)
C50.0158 (4)0.0223 (4)0.0255 (4)−0.0022 (3)0.0017 (3)0.0029 (3)
C60.0135 (3)0.0171 (3)0.0170 (3)0.0011 (3)0.0049 (3)0.0037 (3)
C70.0137 (3)0.0147 (3)0.0115 (3)−0.0003 (2)0.0032 (2)0.0006 (2)
C80.0138 (3)0.0203 (4)0.0173 (3)0.0020 (3)0.0055 (3)0.0012 (3)
C90.0125 (3)0.0175 (3)0.0165 (3)0.0018 (3)0.0040 (3)0.0000 (3)
C100.0148 (3)0.0184 (3)0.0155 (3)0.0009 (3)0.0029 (3)0.0014 (3)
C110.0134 (3)0.0196 (4)0.0160 (3)0.0014 (3)0.0028 (3)0.0018 (3)
C120.0126 (3)0.0161 (3)0.0143 (3)0.0014 (2)0.0027 (2)−0.0004 (2)
C130.0135 (3)0.0161 (3)0.0143 (3)0.0009 (3)0.0032 (2)−0.0006 (2)
C140.0135 (3)0.0193 (4)0.0180 (3)0.0028 (3)0.0011 (3)−0.0015 (3)
C150.0192 (4)0.0188 (4)0.0184 (3)0.0046 (3)0.0008 (3)0.0018 (3)
C160.0218 (4)0.0196 (4)0.0187 (4)0.0020 (3)0.0048 (3)0.0038 (3)
C170.0160 (3)0.0196 (4)0.0177 (3)0.0008 (3)0.0051 (3)0.0016 (3)
Cl1—C131.7393 (9)C4—C51.3951 (14)
S1—C101.6726 (9)C4—H4A0.930
O1—C71.2449 (10)C5—C61.3951 (13)
N1—C71.3340 (11)C5—H5A0.930
N1—C81.4468 (11)C6—C71.4887 (11)
N1—H1N10.84 (1)C8—C91.4930 (12)
N2—C91.2984 (11)C8—H8A0.970
N2—N31.3807 (11)C8—H8B0.970
N3—C101.3467 (11)C11—C121.4677 (12)
N3—H1N30.85 (1)C11—H11A0.930
N4—C91.3797 (11)C12—C131.3987 (11)
N4—N51.3804 (10)C12—C171.4047 (12)
N4—C101.3924 (11)C13—C141.3924 (12)
N5—C111.2816 (11)C14—C151.3879 (13)
C1—C21.3905 (14)C14—H14A0.930
C1—C61.3999 (13)C15—C161.3958 (13)
C1—H1A0.930C15—H15A0.930
C2—C31.3904 (19)C16—C171.3836 (12)
C2—H2A0.930C16—H16A0.930
C3—C41.3879 (19)C17—H17A0.930
C3—H3A0.930
C7—N1—C8120.72 (7)N1—C8—H8A109.0
C7—N1—H1N1121.3 (12)C9—C8—H8A109.0
C8—N1—H1N1117.8 (12)N1—C8—H8B109.0
C9—N2—N3103.64 (7)C9—C8—H8B109.0
C10—N3—N2114.49 (7)H8A—C8—H8B107.8
C10—N3—H1N3124.6 (11)N2—C9—N4111.50 (7)
N2—N3—H1N3120.8 (11)N2—C9—C8127.53 (8)
C9—N4—N5117.35 (7)N4—C9—C8120.96 (7)
C9—N4—C10108.21 (7)N3—C10—N4102.12 (7)
N5—N4—C10134.27 (7)N3—C10—S1127.13 (7)
C11—N5—N4119.60 (7)N4—C10—S1130.74 (7)
C2—C1—C6119.76 (10)N5—C11—C12117.39 (8)
C2—C1—H1A120.1N5—C11—H11A121.3
C6—C1—H1A120.1C12—C11—H11A121.3
C3—C2—C1119.87 (10)C13—C12—C17117.80 (7)
C3—C2—H2A120.1C13—C12—C11121.30 (7)
C1—C2—H2A120.1C17—C12—C11120.90 (8)
C4—C3—C2120.50 (10)C14—C13—C12121.71 (8)
C4—C3—H3A119.7C14—C13—Cl1118.16 (6)
C2—C3—H3A119.7C12—C13—Cl1120.13 (6)
C3—C4—C5120.11 (11)C15—C14—C13119.19 (8)
C3—C4—H4A119.9C15—C14—H14A120.4
C5—C4—H4A119.9C13—C14—H14A120.4
C6—C5—C4119.47 (10)C14—C15—C16120.29 (8)
C6—C5—H5A120.3C14—C15—H15A119.9
C4—C5—H5A120.3C16—C15—H15A119.9
C5—C6—C1120.28 (8)C17—C16—C15119.94 (8)
C5—C6—C7122.17 (8)C17—C16—H16A120.0
C1—C6—C7117.52 (8)C15—C16—H16A120.0
O1—C7—N1120.84 (8)C16—C17—C12121.04 (8)
O1—C7—C6121.35 (8)C16—C17—H17A119.5
N1—C7—C6117.81 (7)C12—C17—H17A119.5
N1—C8—C9112.71 (7)
C9—N2—N3—C100.01 (11)C10—N4—C9—C8176.80 (8)
C9—N4—N5—C11−173.61 (8)N1—C8—C9—N23.33 (13)
C10—N4—N5—C1111.79 (14)N1—C8—C9—N4−175.30 (7)
C6—C1—C2—C3−0.94 (15)N2—N3—C10—N4−1.18 (10)
C1—C2—C3—C4−0.30 (16)N2—N3—C10—S1177.48 (7)
C2—C3—C4—C51.02 (16)C9—N4—C10—N31.84 (9)
C3—C4—C5—C6−0.50 (15)N5—N4—C10—N3176.80 (9)
C4—C5—C6—C1−0.73 (14)C9—N4—C10—S1−176.74 (7)
C4—C5—C6—C7−178.80 (8)N5—N4—C10—S1−1.79 (15)
C2—C1—C6—C51.45 (13)N4—N5—C11—C12−179.19 (7)
C2—C1—C6—C7179.61 (8)N5—C11—C12—C13−169.43 (8)
C8—N1—C7—O11.88 (12)N5—C11—C12—C1710.21 (12)
C8—N1—C7—C6−178.27 (7)C17—C12—C13—C14−1.71 (12)
C5—C6—C7—O1148.96 (9)C11—C12—C13—C14177.95 (8)
C1—C6—C7—O1−29.16 (12)C17—C12—C13—Cl1178.51 (6)
C5—C6—C7—N1−30.88 (12)C11—C12—C13—Cl1−1.83 (11)
C1—C6—C7—N1151.00 (8)C12—C13—C14—C150.51 (13)
C7—N1—C8—C9−83.83 (10)Cl1—C13—C14—C15−179.70 (7)
N3—N2—C9—N41.23 (10)C13—C14—C15—C160.73 (13)
N3—N2—C9—C8−177.50 (8)C14—C15—C16—C17−0.71 (14)
N5—N4—C9—N2−177.97 (7)C15—C16—C17—C12−0.54 (14)
C10—N4—C9—N2−2.04 (10)C13—C12—C17—C161.72 (13)
N5—N4—C9—C80.86 (12)C11—C12—C17—C16−177.94 (8)
D—H···AD—HH···AD···AD—H···A
N3—H1N3···O1i0.85 (1)1.89 (1)2.7362 (10)175 (1)
N1—H1N1···O1ii0.84 (1)2.29 (1)2.9450 (10)134 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N3—H1N3⋯O1i0.85 (1)1.89 (1)2.7362 (10)175 (1)
N1—H1N1⋯O1ii0.84 (1)2.29 (1)2.9450 (10)134 (2)

Symmetry codes: (i) ; (ii) .

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