3-Benzamidomethyl-4-[(E)-2-chloro­benzyl­ideneamino]-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Jebas, S.R.; Rao, J.N.; Kalluraya, B.

doi:10.1107/S1600536808040361

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o48

doi:10.1107/S1600536808040361

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3-Benzamidomethyl-4-[(E)-2-chlorobenzylideneamino]-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^* Samuel Robinson Jebas,^a ‡ Jyothi N. Rao ^b and B. Kalluraya ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, Mangalore 574 199, India
^*Correspondence e-mail: hkfun@usm.my

(Received 6 November 2008; accepted 1 December 2008; online 10 December 2008)

In the title compound, C₁₇H₁₄ClN₅OS, 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)°. Intermolecular N—H⋯O hydrogen bonds link the molecules into layers parallel to the (100) planes, and centrosymmetric π–π stacking interactions [centroid–centroid distance = 3.7717 (5) Å] are formed between benzene rings in neighbouring layers.

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_r = 371.84
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.098
S = 1.09
7463 reflections
234 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1N3⋯O1ⁱ	0.85 (1)	1.89 (1)	2.7362 (10)	175 (1)
N1—H1N1⋯O1ⁱⁱ	0.84 (1)	2.29 (1)	2.9450 (10)	134 (2)
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808040361/bi2320sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808040361/bi2320Isup2.hkl

checkCIF report

Comment top

1,2,4-Triazoles and their derivatives represent a rapidly developing field in modern heterocyclic chemistry, in part due to their antibacterial, antifungal, antitubercular, anticancer (Kalluraya et al., 1996), antitumor (Al-Soud et al., 2003), anticonvulsant (Almasirad et al., 2004), anti-inflammatory, and analgesic properties (Amir & Shikha, 2004). Certain 1,2,4-triazoles also find applications in the preparation of photographic plates, polymers, and as analytical agents (Kawashima et al., 1986). In continuation of our interest in the synthesis of chemically and biologically important heterocycles, we report here a substituted 1,2,4-triazole Schiff base.

In the title compound (Fig. 1), the dihedral angles formed by the triazole (N2/N3/C10/N4/C9) ring with the two benzene rings (C1–C6; C12–C17) are 66.88 (3)° and 19.16 (3)° respectively. The benzene rings (C1–C6; C12–C17) form a dihedral angle of 78.40 (3)°, indicating that they are inclined to each other. The structure contains intermolecular N—H···O hydrogen bonds (see Table), linking the molecules into two-dimensional networks parallel to the (100) planes (Fig. 2). Between layers, π—π stacking interactions are formed between inversion-related benzene rings (C12–C17 and its symmetry equivalent 2-x, 2-y, 1-z) with centroid-centroid distance 3.7717 (5) Å.

Related literature top

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 top

The title compound was obtained by refluxing N-[(4-amino-5-sulfanyl-4H-1, 2,4-triazol-3-yl)methyl]benzamide (0.01 mol) and 2-chlorobenzaldehyde (0.01 mol) in ethanol (30 ml) with 3 drops of concentrated sulfuric acid for 5 h. The solid product obtained was collected by filtration, washed with ethanol and dried. The product was then recrystallized using ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Projection down the a axis onto one two-dimensional hydrogen-bond network.

3-Benzamidomethyl-4-[(E)-2-chlorobenzylideneamino]-1H-1,2,4- triazole-5(4H)-thione top

Crystal data top

C₁₇H₁₄ClN₅OS	F(000) = 768
M_r = 371.84	D_x = 1.454 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9004 reflections
a = 17.0185 (6) Å	θ = 2.6–26.3°
b = 8.0905 (3) Å	µ = 0.36 mm⁻¹
c = 12.8292 (5) Å	T = 100 K
β = 105.962 (2)°	Plate, colourless
V = 1698.32 (11) Å³	0.70 × 0.48 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	7463 independent reflections
Radiation source: fine-focus sealed tube	6349 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 35.0°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→27
T_min = 0.785, T_max = 0.949	k = −12→13
57891 measured reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0502P)² + 0.4785P] where P = (F_o² + 2F_c²)/3
7463 reflections	(Δ/σ)_max = 0.004
234 parameters	Δρ_max = 0.59 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₇H₁₄ClN₅OS	V = 1698.32 (11) Å³
M_r = 371.84	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.0185 (6) Å	µ = 0.36 mm⁻¹
b = 8.0905 (3) Å	T = 100 K
c = 12.8292 (5) Å	0.70 × 0.48 × 0.15 mm
β = 105.962 (2)°

Data collection top

Bruker SMART APEXII CCD diffractometer	7463 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	6349 reflections with I > 2σ(I)
T_min = 0.785, T_max = 0.949	R_int = 0.025
57891 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	2 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.59 e Å⁻³
7463 reflections	Δρ_min = −0.23 e Å⁻³
234 parameters

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
Cl1	1.007210 (13)	1.03657 (3)	0.261198 (17)	0.02066 (5)
S1	0.757666 (14)	1.12198 (3)	0.021681 (19)	0.02205 (6)
O1	0.52774 (4)	1.20878 (8)	0.36983 (5)	0.01823 (12)
N1	0.52114 (5)	0.94734 (9)	0.30979 (6)	0.01683 (13)
N2	0.56478 (5)	1.09220 (10)	0.13014 (6)	0.01817 (13)
N3	0.60840 (5)	1.13484 (10)	0.05794 (6)	0.01859 (14)
N4	0.69550 (4)	1.02508 (9)	0.19194 (6)	0.01486 (12)
N5	0.75857 (4)	0.95136 (10)	0.26923 (6)	0.01636 (13)
C1	0.37543 (6)	1.16562 (13)	0.41825 (8)	0.02102 (16)
H1A	0.4129	1.2333	0.4659	0.025*
C2	0.29456 (7)	1.16030 (15)	0.42187 (9)	0.0288 (2)
H2A	0.2779	1.2232	0.4726	0.035*
C3	0.23860 (7)	1.06069 (16)	0.34943 (11)	0.0332 (3)
H3A	0.1846	1.0569	0.3522	0.040*
C4	0.26273 (6)	0.96688 (15)	0.27305 (10)	0.0308 (2)
H4A	0.2247	0.9019	0.2241	0.037*
C5	0.34392 (6)	0.96984 (12)	0.26950 (8)	0.02199 (17)
H5A	0.3603	0.9064	0.2188	0.026*
C6	0.40030 (5)	1.06870 (11)	0.34268 (7)	0.01574 (14)
C7	0.48744 (5)	1.07999 (10)	0.34185 (6)	0.01337 (13)
C8	0.60617 (5)	0.94817 (11)	0.30987 (7)	0.01689 (14)
H8A	0.6263	0.8354	0.3162	0.020*
H8B	0.6376	1.0090	0.3727	0.020*
C9	0.61919 (5)	1.02410 (10)	0.20985 (7)	0.01548 (14)
C10	0.68828 (5)	1.09511 (11)	0.09059 (7)	0.01650 (14)
C11	0.83182 (5)	0.96240 (11)	0.26128 (7)	0.01659 (14)
H11A	0.8436	1.0204	0.2048	0.020*
C12	0.89642 (5)	0.87989 (10)	0.34477 (6)	0.01453 (13)
C13	0.97907 (5)	0.90723 (10)	0.35310 (6)	0.01472 (13)
C14	1.04079 (5)	0.83357 (11)	0.43414 (7)	0.01758 (15)
H14A	1.0954	0.8540	0.4387	0.021*
C15	1.01981 (6)	0.72926 (11)	0.50811 (7)	0.01963 (16)
H15A	1.0606	0.6804	0.5630	0.024*
C16	0.93781 (6)	0.69731 (12)	0.50042 (7)	0.02018 (16)
H16A	0.9240	0.6264	0.5497	0.024*
C17	0.87707 (5)	0.77125 (11)	0.41949 (7)	0.01766 (14)
H17A	0.8226	0.7487	0.4145	0.021*
H1N3	0.5848 (9)	1.1788 (19)	−0.0026 (9)	0.034 (4)*
H1N1	0.4932 (9)	0.8627 (15)	0.2855 (13)	0.040 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.01679 (9)	0.02638 (11)	0.01858 (9)	−0.00361 (7)	0.00446 (7)	0.00349 (7)
S1	0.01723 (10)	0.03144 (12)	0.01831 (10)	0.00069 (8)	0.00629 (7)	0.00525 (8)
O1	0.0181 (3)	0.0162 (3)	0.0190 (3)	−0.0035 (2)	0.0027 (2)	−0.0028 (2)
N1	0.0142 (3)	0.0155 (3)	0.0217 (3)	−0.0019 (2)	0.0065 (2)	−0.0035 (2)
N2	0.0139 (3)	0.0220 (3)	0.0183 (3)	0.0027 (3)	0.0040 (2)	0.0024 (3)
N3	0.0147 (3)	0.0234 (3)	0.0168 (3)	0.0032 (3)	0.0030 (2)	0.0044 (3)
N4	0.0115 (3)	0.0184 (3)	0.0143 (3)	0.0024 (2)	0.0029 (2)	0.0018 (2)
N5	0.0130 (3)	0.0202 (3)	0.0147 (3)	0.0035 (2)	0.0020 (2)	0.0013 (2)
C1	0.0211 (4)	0.0247 (4)	0.0198 (4)	0.0061 (3)	0.0098 (3)	0.0049 (3)
C2	0.0242 (5)	0.0374 (5)	0.0302 (5)	0.0127 (4)	0.0163 (4)	0.0145 (4)
C3	0.0160 (4)	0.0428 (6)	0.0430 (6)	0.0060 (4)	0.0117 (4)	0.0218 (5)
C4	0.0146 (4)	0.0349 (6)	0.0396 (6)	−0.0037 (4)	0.0015 (4)	0.0115 (4)
C5	0.0158 (4)	0.0223 (4)	0.0255 (4)	−0.0022 (3)	0.0017 (3)	0.0029 (3)
C6	0.0135 (3)	0.0171 (3)	0.0170 (3)	0.0011 (3)	0.0049 (3)	0.0037 (3)
C7	0.0137 (3)	0.0147 (3)	0.0115 (3)	−0.0003 (2)	0.0032 (2)	0.0006 (2)
C8	0.0138 (3)	0.0203 (4)	0.0173 (3)	0.0020 (3)	0.0055 (3)	0.0012 (3)
C9	0.0125 (3)	0.0175 (3)	0.0165 (3)	0.0018 (3)	0.0040 (3)	0.0000 (3)
C10	0.0148 (3)	0.0184 (3)	0.0155 (3)	0.0009 (3)	0.0029 (3)	0.0014 (3)
C11	0.0134 (3)	0.0196 (4)	0.0160 (3)	0.0014 (3)	0.0028 (3)	0.0018 (3)
C12	0.0126 (3)	0.0161 (3)	0.0143 (3)	0.0014 (2)	0.0027 (2)	−0.0004 (2)
C13	0.0135 (3)	0.0161 (3)	0.0143 (3)	0.0009 (3)	0.0032 (2)	−0.0006 (2)
C14	0.0135 (3)	0.0193 (4)	0.0180 (3)	0.0028 (3)	0.0011 (3)	−0.0015 (3)
C15	0.0192 (4)	0.0188 (4)	0.0184 (3)	0.0046 (3)	0.0008 (3)	0.0018 (3)
C16	0.0218 (4)	0.0196 (4)	0.0187 (4)	0.0020 (3)	0.0048 (3)	0.0038 (3)
C17	0.0160 (3)	0.0196 (4)	0.0177 (3)	0.0008 (3)	0.0051 (3)	0.0016 (3)

Geometric parameters (Å, º) top

Cl1—C13	1.7393 (9)	C4—C5	1.3951 (14)
S1—C10	1.6726 (9)	C4—H4A	0.930
O1—C7	1.2449 (10)	C5—C6	1.3951 (13)
N1—C7	1.3340 (11)	C5—H5A	0.930
N1—C8	1.4468 (11)	C6—C7	1.4887 (11)
N1—H1N1	0.84 (1)	C8—C9	1.4930 (12)
N2—C9	1.2984 (11)	C8—H8A	0.970
N2—N3	1.3807 (11)	C8—H8B	0.970
N3—C10	1.3467 (11)	C11—C12	1.4677 (12)
N3—H1N3	0.85 (1)	C11—H11A	0.930
N4—C9	1.3797 (11)	C12—C13	1.3987 (11)
N4—N5	1.3804 (10)	C12—C17	1.4047 (12)
N4—C10	1.3924 (11)	C13—C14	1.3924 (12)
N5—C11	1.2816 (11)	C14—C15	1.3879 (13)
C1—C2	1.3905 (14)	C14—H14A	0.930
C1—C6	1.3999 (13)	C15—C16	1.3958 (13)
C1—H1A	0.930	C15—H15A	0.930
C2—C3	1.3904 (19)	C16—C17	1.3836 (12)
C2—H2A	0.930	C16—H16A	0.930
C3—C4	1.3879 (19)	C17—H17A	0.930
C3—H3A	0.930

C7—N1—C8	120.72 (7)	N1—C8—H8A	109.0
C7—N1—H1N1	121.3 (12)	C9—C8—H8A	109.0
C8—N1—H1N1	117.8 (12)	N1—C8—H8B	109.0
C9—N2—N3	103.64 (7)	C9—C8—H8B	109.0
C10—N3—N2	114.49 (7)	H8A—C8—H8B	107.8
C10—N3—H1N3	124.6 (11)	N2—C9—N4	111.50 (7)
N2—N3—H1N3	120.8 (11)	N2—C9—C8	127.53 (8)
C9—N4—N5	117.35 (7)	N4—C9—C8	120.96 (7)
C9—N4—C10	108.21 (7)	N3—C10—N4	102.12 (7)
N5—N4—C10	134.27 (7)	N3—C10—S1	127.13 (7)
C11—N5—N4	119.60 (7)	N4—C10—S1	130.74 (7)
C2—C1—C6	119.76 (10)	N5—C11—C12	117.39 (8)
C2—C1—H1A	120.1	N5—C11—H11A	121.3
C6—C1—H1A	120.1	C12—C11—H11A	121.3
C3—C2—C1	119.87 (10)	C13—C12—C17	117.80 (7)
C3—C2—H2A	120.1	C13—C12—C11	121.30 (7)
C1—C2—H2A	120.1	C17—C12—C11	120.90 (8)
C4—C3—C2	120.50 (10)	C14—C13—C12	121.71 (8)
C4—C3—H3A	119.7	C14—C13—Cl1	118.16 (6)
C2—C3—H3A	119.7	C12—C13—Cl1	120.13 (6)
C3—C4—C5	120.11 (11)	C15—C14—C13	119.19 (8)
C3—C4—H4A	119.9	C15—C14—H14A	120.4
C5—C4—H4A	119.9	C13—C14—H14A	120.4
C6—C5—C4	119.47 (10)	C14—C15—C16	120.29 (8)
C6—C5—H5A	120.3	C14—C15—H15A	119.9
C4—C5—H5A	120.3	C16—C15—H15A	119.9
C5—C6—C1	120.28 (8)	C17—C16—C15	119.94 (8)
C5—C6—C7	122.17 (8)	C17—C16—H16A	120.0
C1—C6—C7	117.52 (8)	C15—C16—H16A	120.0
O1—C7—N1	120.84 (8)	C16—C17—C12	121.04 (8)
O1—C7—C6	121.35 (8)	C16—C17—H17A	119.5
N1—C7—C6	117.81 (7)	C12—C17—H17A	119.5
N1—C8—C9	112.71 (7)

C9—N2—N3—C10	0.01 (11)	C10—N4—C9—C8	176.80 (8)
C9—N4—N5—C11	−173.61 (8)	N1—C8—C9—N2	3.33 (13)
C10—N4—N5—C11	11.79 (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—S1	177.48 (7)
C2—C3—C4—C5	1.02 (16)	C9—N4—C10—N3	1.84 (9)
C3—C4—C5—C6	−0.50 (15)	N5—N4—C10—N3	176.80 (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—C5	1.45 (13)	N4—N5—C11—C12	−179.19 (7)
C2—C1—C6—C7	179.61 (8)	N5—C11—C12—C13	−169.43 (8)
C8—N1—C7—O1	1.88 (12)	N5—C11—C12—C17	10.21 (12)
C8—N1—C7—C6	−178.27 (7)	C17—C12—C13—C14	−1.71 (12)
C5—C6—C7—O1	148.96 (9)	C11—C12—C13—C14	177.95 (8)
C1—C6—C7—O1	−29.16 (12)	C17—C12—C13—Cl1	178.51 (6)
C5—C6—C7—N1	−30.88 (12)	C11—C12—C13—Cl1	−1.83 (11)
C1—C6—C7—N1	151.00 (8)	C12—C13—C14—C15	0.51 (13)
C7—N1—C8—C9	−83.83 (10)	Cl1—C13—C14—C15	−179.70 (7)
N3—N2—C9—N4	1.23 (10)	C13—C14—C15—C16	0.73 (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—C16	1.72 (13)
N5—N4—C9—C8	0.86 (12)	C11—C12—C17—C16	−177.94 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1ⁱ	0.85 (1)	1.89 (1)	2.7362 (10)	175 (1)
N1—H1N1···O1ⁱⁱ	0.84 (1)	2.29 (1)	2.9450 (10)	134 (2)

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₄ClN₅OS
M_r	371.84
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	17.0185 (6), 8.0905 (3), 12.8292 (5)
β (°)	105.962 (2)
V (Å³)	1698.32 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.70 × 0.48 × 0.15

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.785, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	57891, 7463, 6349
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.098, 1.09
No. of reflections	7463
No. of parameters	234
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O1ⁱ	0.85 (1)	1.89 (1)	2.7362 (10)	175 (1)
N1—H1N1···O1ⁱⁱ	0.84 (1)	2.29 (1)	2.9450 (10)	134 (2)

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) −x+1, y−1/2, −z+1/2.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

H-KF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a postdoctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

Almasirad, A., Tabatabai, S. A., Faizi, M., Kebriaeezadeh, A., Mehrabi, N., Dalvandi, A. & Shafiee, A. (2004). Bioorg. Med. Chem. Lett. 14, 6057–6059. Web of Science CrossRef PubMed CAS Google Scholar
Al-Soud, Y. A., Al-Masoudi, N. A. & Ferwanah, A. R. S. (2003). Bioorg. Med. Chem. 11, 1701–1708. Web of Science CrossRef PubMed CAS Google Scholar
Amir, M. & Shikha, K. (2004). Eur. J. Med. Chem. 39, 535–545. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kalluraya, B., Shetty, S. N., Gunaga, P. & Holla, B. S. (1996). Boll. Chim. Farm. 135, 638–642. CAS PubMed Google Scholar
Kawashima, Y., Ishikawa, H., Kida, S., Tanaka, T. & Masuda, T. (1987). Chem. Abstr. 106, 138475x. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

3-Benzamido­methyl-4-[(E)-2-chloro­benzyl­­idene­amino]-1H-1,2,4-triazole-5(4H)-thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

3-Benzamidomethyl-4-[(E)-2-chlorobenzylideneamino]-1H-1,2,4-triazole-5(4H)-thione