Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020326/pk2019sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020326/pk2019Isup2.hkl |
CCDC reference: 648085
5-(Thien-2-ylmethyl)4, 4'-bi-1, 2, 4-triazol-3(2H)-one (0.001 mol) was refluxed with sodium metal (0.001 mol) in absolute ethanol (50 ml) for 1 h. Chloro acetone (0.001 mol) was added and the solution refluxed for 8 h. The resulting solution was filtered and then evaporated under reduced pressure. The solid residue was crystallized from absolute ethanol-diethylether (1:4). (Yield: 52%; m.p. 438–439 K).
H atoms were placed in idealized positions and were constrained using riding models at distances ranging between 0.93–0.97Å with isotropic displacement parameters derived from their carrier atoms (Uiso(H) = 1.2Ueq(C) or 1.5Ueq(CMe).
In a continuing search for pharmacologically active, 1,2,4-triazol and 1,2,4 triazol-5-one compounds it was found that most azole fungicides have been developed for diseases of cereal crops; examples include fluconazole (Ichikawa et al., 2001), ravuconazole (Ueda, 2003) and posaconazole (Kim et al., 2003). The properties of 1,2,4-triazole derivatives have broad-spectrum biological effects, such as insecticidal (Tsuda et al., 2004), herbicidal (Chai et al., 2003), anticonvulsant (Er-Rahimini & Mornet, 1992), antitumour (Nakip et al., 1994) and plant growth regulatory activities (Jenkins et al., 1989). Di- or tri-substituted 1,2,4-triazole derivatives have also been reported to show antituberculotic and antimicrobial activities (Demirbaş et al., 2004). Additionally, thermally stable polymers containing the 1, 2, 4-triazole moiety have been prepared (Shaikh et al., 2002).
The title compound (I)(Fig.1) consists of a triazole ring with an acetonyl group substituted at N4, a disordered (2,5-thienyl methyl) group substituted at C2, a 1,2,4-triazole ring substituted at N1 and an oxo O atom at C5. The N1—C5 bond length, 1.396 (3) Å, agrees with reported values [1.390 (3)Å in C13H13ClN4O2 (Çoruh, Kahveci, Şaşmaz, Aǧar, Kim & Erdönmez, 2003), 1.387 (3)Å in C12H11ClN4O2 (Çoruh, Kahveci, Şaşmaz, Aǧar & Kim, 2003)]. In the 1,2,4-triazole ring the N12—N13 bond length, 1.404 (4) Å, agrees with reported values [1.403 (8)Å in C19H18N6O2S (Sancak et al., 2005)].
The presence of a substituent on N4 causes a lengthening of the N—N bond length [N3—N4= 1.390 (3) Å] with respect to the corresponding bonds in 5-(2-chlorophenyl)-4-phenyl-3,4-dihydro-2H-1,2,4-triazole-3-thione [N—N= 1.374 (2) Å; Puviarasan et al., 1999] and in 4-methyl-1,2,4- triazole and 1-methyltetrazole [N—N= 1.344 (2) Å; Palmer & Parsons, 1996]. The S—C bond lengths [S21—C22= 1.681 (4)Å and S21—C25= 1.6807 Å] agree with values reported in the literature [S41—C44=1.676 (4)Å and S41—C41=1.689 (3)Å (Vrabel et al., 2005), C14—S1=1.692Å and C11—S1=1.708Å (Yılmaz et al., 2006)].
The thiophene ring is disordered over two positions, corresponding to rotation of approximately 180° about the single C21—C22 bond, with a major-minor ratio of about 50:50. Intermolecular hydrogen bonds are effective in stabilizing the crystal structure.
For related literature, see: Chai et al. (2003); Demirbaş et al. (2004); Er-Rahimini & Mornet (1992); Ichikawa et al. (2001); Jenkins et al. (1989); Kim et al. (2003); Nakib et al. (1994); Palmer & Parsons (1996); Puviarason et al. (1999); Sancak et al. (2005); Shaikh et al. (2002); Sheldrick (1997a, 1997b); Tsuda et al. (2004); Ueda (2003); Vrábel et al. (2005); Yılmaz, Arslan, Kazak, Sancak & Er (2006); Çoruh, Kahveci, Şaşmaz, Aǧar & Kim (2003); Çoruh, Kahveci, Şaşmaz, Aǧar, Kim & Erdönmez (2003).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. An ORTEP drawing of (I), with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
C12H12N6O2S | F(000) = 632 |
Mr = 304.34 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1214 reflections |
a = 5.8357 (8) Å | θ = 2.5–25.3° |
b = 32.084 (4) Å | µ = 0.25 mm−1 |
c = 7.4958 (10) Å | T = 293 K |
β = 95.087 (3)° | Irregular, colorless |
V = 1397.9 (3) Å3 | 0.37 × 0.30 × 0.13 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 2412 independent reflections |
Radiation source: fine-focus sealed tube | 1214 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.086 |
φ and ω scans | θmax = 25.3°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −6→7 |
Tmin = 0.685, Tmax = 0.969 | k = −38→38 |
6559 measured reflections | l = −8→5 |
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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.028P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.82 | (Δ/σ)max < 0.001 |
2412 reflections | Δρmax = 0.17 e Å−3 |
201 parameters | Δρmin = −0.17 e Å−3 |
183 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0045 (8) |
C12H12N6O2S | V = 1397.9 (3) Å3 |
Mr = 304.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 5.8357 (8) Å | µ = 0.25 mm−1 |
b = 32.084 (4) Å | T = 293 K |
c = 7.4958 (10) Å | 0.37 × 0.30 × 0.13 mm |
β = 95.087 (3)° |
Bruker SMART CCD area-detector diffractometer | 2412 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1214 reflections with I > 2σ(I) |
Tmin = 0.685, Tmax = 0.969 | Rint = 0.086 |
6559 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 183 restraints |
wR(F2) = 0.089 | H-atom parameters constrained |
S = 0.82 | Δρmax = 0.17 e Å−3 |
2412 reflections | Δρmin = −0.17 e Å−3 |
201 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C21 | −0.1123 (5) | 0.62882 (8) | 0.4109 (4) | 0.0508 (8) | |
H21A | −0.2652 | 0.6397 | 0.4233 | 0.061* | |
H21B | −0.1177 | 0.6134 | 0.2992 | 0.061* | |
C22 | 0.0521 (5) | 0.66449 (9) | 0.4029 (4) | 0.0505 (7) | 0.50 |
C23 | 0.238 (2) | 0.6635 (5) | 0.313 (2) | 0.0758 (7) | 0.50 |
H23 | 0.2751 | 0.6408 | 0.2430 | 0.091* | 0.50 |
C24 | 0.379 (3) | 0.7009 (3) | 0.332 (2) | 0.0774 (13) | 0.50 |
H24 | 0.5122 | 0.7057 | 0.2763 | 0.093* | 0.50 |
C25 | 0.2859 (7) | 0.72750 (11) | 0.4445 (5) | 0.0764 (12) | 0.50 |
H25 | 0.3509 | 0.7531 | 0.4787 | 0.092* | 0.50 |
S21 | 0.0395 (7) | 0.70954 (11) | 0.5162 (5) | 0.0742 (7) | 0.50 |
C22' | 0.0521 (5) | 0.66449 (9) | 0.4029 (4) | 0.0505 (7) | 0.50 |
C23' | 0.021 (3) | 0.7032 (4) | 0.4704 (18) | 0.0742 (7) | 0.50 |
H23' | −0.1058 | 0.7117 | 0.5278 | 0.089* | 0.50 |
C24' | 0.2230 (14) | 0.7298 (3) | 0.4377 (10) | 0.0764 (12) | 0.50 |
H24' | 0.2445 | 0.7570 | 0.4781 | 0.092* | 0.50 |
C25' | 0.366 (3) | 0.7094 (3) | 0.344 (2) | 0.0774 (13) | 0.50 |
H25' | 0.5009 | 0.7210 | 0.3092 | 0.093* | 0.50 |
S21' | 0.2842 (6) | 0.66048 (14) | 0.2919 (6) | 0.0758 (7) | 0.50 |
N1 | −0.0889 (3) | 0.60701 (6) | 0.7383 (3) | 0.0403 (6) | |
C2 | −0.0471 (4) | 0.59995 (8) | 0.5620 (4) | 0.0399 (7) | |
N3 | 0.0634 (4) | 0.56527 (7) | 0.5507 (3) | 0.0457 (6) | |
N4 | 0.0926 (3) | 0.54966 (6) | 0.7243 (3) | 0.0419 (6) | |
C5 | −0.0098 (4) | 0.57328 (8) | 0.8443 (4) | 0.0421 (7) | |
O51 | −0.0271 (3) | 0.56817 (5) | 1.0029 (3) | 0.0559 (6) | |
N11 | −0.2326 (4) | 0.63674 (6) | 0.7998 (3) | 0.0439 (6) | |
O41 | 0.5537 (3) | 0.53282 (6) | 0.7185 (3) | 0.0744 (7) | |
C41 | 0.1784 (4) | 0.50814 (7) | 0.7550 (4) | 0.0456 (7) | |
H41A | 0.0980 | 0.4897 | 0.6682 | 0.055* | |
H41B | 0.1426 | 0.4993 | 0.8730 | 0.055* | |
C42 | 0.4318 (5) | 0.50339 (9) | 0.7430 (3) | 0.0440 (7) | |
C43 | 0.5203 (5) | 0.45964 (8) | 0.7612 (4) | 0.0584 (8) | |
H43A | 0.6821 | 0.4601 | 0.7981 | 0.088* | |
H43B | 0.4949 | 0.4456 | 0.6481 | 0.088* | |
H43C | 0.4407 | 0.4451 | 0.8492 | 0.088* | |
N12 | −0.3510 (6) | 0.68921 (9) | 0.9474 (4) | 0.0846 (9) | |
N13 | −0.5427 (5) | 0.66589 (10) | 0.8810 (4) | 0.0817 (9) | |
C12 | −0.4651 (5) | 0.63472 (10) | 0.7955 (4) | 0.0630 (9) | |
H12 | −0.5556 | 0.6139 | 0.7391 | 0.076* | |
C11 | −0.1712 (6) | 0.67082 (9) | 0.8970 (4) | 0.0649 (9) | |
H11 | −0.0206 | 0.6798 | 0.9241 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C21 | 0.0548 (19) | 0.0479 (18) | 0.049 (2) | 0.0007 (15) | 0.0017 (16) | 0.0037 (15) |
C22 | 0.0550 (17) | 0.0433 (15) | 0.0531 (18) | 0.0029 (13) | 0.0045 (15) | 0.0094 (14) |
C23 | 0.0557 (16) | 0.0810 (11) | 0.0934 (14) | 0.0008 (12) | 0.0219 (11) | 0.0207 (10) |
C24 | 0.066 (2) | 0.074 (3) | 0.092 (3) | −0.010 (2) | 0.0082 (18) | 0.024 (2) |
C25 | 0.085 (3) | 0.059 (2) | 0.085 (2) | −0.016 (2) | 0.002 (2) | 0.0139 (18) |
S21 | 0.0963 (14) | 0.0515 (13) | 0.078 (2) | −0.0098 (11) | 0.0229 (14) | −0.0079 (11) |
C22' | 0.0550 (17) | 0.0433 (15) | 0.0531 (18) | 0.0029 (13) | 0.0045 (15) | 0.0094 (14) |
C23' | 0.0963 (14) | 0.0515 (13) | 0.078 (2) | −0.0098 (11) | 0.0229 (14) | −0.0079 (11) |
C24' | 0.085 (3) | 0.059 (2) | 0.085 (2) | −0.016 (2) | 0.002 (2) | 0.0139 (18) |
C25' | 0.066 (2) | 0.074 (3) | 0.092 (3) | −0.010 (2) | 0.0082 (18) | 0.024 (2) |
S21' | 0.0557 (16) | 0.0810 (11) | 0.0934 (14) | 0.0008 (12) | 0.0219 (11) | 0.0207 (10) |
N1 | 0.0394 (14) | 0.0349 (13) | 0.0476 (16) | 0.0072 (11) | 0.0093 (12) | 0.0006 (12) |
C2 | 0.0347 (17) | 0.0408 (18) | 0.0445 (19) | −0.0041 (14) | 0.0048 (14) | −0.0011 (15) |
N3 | 0.0496 (16) | 0.0409 (14) | 0.0481 (16) | 0.0039 (11) | 0.0119 (12) | 0.0005 (12) |
N4 | 0.0441 (15) | 0.0343 (13) | 0.0481 (16) | 0.0058 (11) | 0.0087 (12) | 0.0043 (12) |
C5 | 0.0342 (18) | 0.0373 (17) | 0.055 (2) | −0.0024 (13) | 0.0060 (16) | 0.0045 (17) |
O51 | 0.0665 (15) | 0.0568 (13) | 0.0458 (13) | 0.0074 (10) | 0.0124 (11) | 0.0097 (11) |
N11 | 0.0423 (15) | 0.0369 (13) | 0.0535 (16) | 0.0049 (12) | 0.0103 (12) | −0.0045 (12) |
O41 | 0.0484 (14) | 0.0548 (13) | 0.121 (2) | −0.0130 (11) | 0.0126 (13) | −0.0001 (13) |
C41 | 0.0428 (18) | 0.0358 (16) | 0.059 (2) | 0.0027 (13) | 0.0107 (15) | 0.0047 (14) |
C42 | 0.0396 (17) | 0.0449 (18) | 0.0478 (19) | 0.0000 (15) | 0.0052 (15) | −0.0050 (15) |
C43 | 0.0533 (19) | 0.0534 (18) | 0.069 (2) | 0.0144 (15) | 0.0101 (16) | 0.0003 (16) |
N12 | 0.093 (3) | 0.075 (2) | 0.088 (2) | 0.0220 (19) | 0.018 (2) | −0.0249 (17) |
N13 | 0.072 (2) | 0.086 (2) | 0.092 (2) | 0.0272 (19) | 0.0309 (19) | −0.0095 (18) |
C12 | 0.047 (2) | 0.065 (2) | 0.078 (3) | 0.0035 (17) | 0.0101 (18) | −0.0026 (19) |
C11 | 0.067 (2) | 0.055 (2) | 0.074 (2) | 0.0001 (18) | 0.0108 (19) | −0.0189 (19) |
C21—C2 | 1.487 (3) | C2—N3 | 1.292 (3) |
C21—C22 | 1.498 (3) | N3—N4 | 1.390 (3) |
C21—H21A | 0.9700 | N4—C5 | 1.355 (3) |
C21—H21B | 0.9700 | N4—C41 | 1.434 (3) |
C22—C23 | 1.330 (13) | C5—O51 | 1.213 (3) |
C22—S21 | 1.681 (4) | N11—C11 | 1.345 (3) |
C23—C24 | 1.456 (17) | N11—C12 | 1.356 (3) |
C23—H23 | 0.9300 | O41—C42 | 1.206 (3) |
C24—C25 | 1.345 (10) | C41—C42 | 1.497 (3) |
C24—H24 | 0.9300 | C41—H41A | 0.9700 |
C25—S21 | 1.6807 | C41—H41B | 0.9700 |
C25—H25 | 0.9300 | C42—C43 | 1.498 (3) |
C23'—C24' | 1.493 (13) | C43—H43A | 0.9600 |
C23'—H23' | 0.9300 | C43—H43B | 0.9600 |
C24'—C25' | 1.313 (10) | C43—H43C | 0.9600 |
C24'—H24' | 0.9300 | N12—C11 | 1.289 (3) |
C25'—S21' | 1.675 (11) | N12—N13 | 1.400 (4) |
C25'—H25' | 0.9300 | N13—C12 | 1.291 (3) |
N1—N11 | 1.376 (3) | C12—H12 | 0.9300 |
N1—C2 | 1.383 (3) | C11—H11 | 0.9300 |
N1—C5 | 1.396 (3) | ||
C2—C21—C22 | 112.6 (2) | C5—N4—N3 | 113.2 (2) |
C2—C21—H21A | 109.1 | C5—N4—C41 | 125.5 (2) |
C22—C21—H21A | 109.1 | N3—N4—C41 | 119.8 (2) |
C2—C21—H21B | 109.1 | O51—C5—N4 | 130.9 (3) |
C22—C21—H21B | 109.1 | O51—C5—N1 | 127.6 (3) |
H21A—C21—H21B | 107.8 | N4—C5—N1 | 101.5 (2) |
C23—C22—C21 | 123.8 (8) | C11—N11—C12 | 105.7 (3) |
C23—C22—S21 | 110.7 (8) | C11—N11—N1 | 127.1 (3) |
C21—C22—S21 | 125.4 (2) | C12—N11—N1 | 126.7 (2) |
C22—C23—C24 | 113.9 (13) | N4—C41—C42 | 114.7 (2) |
C22—C23—H23 | 123.0 | N4—C41—H41A | 108.6 |
C24—C23—H23 | 123.0 | C42—C41—H41A | 108.6 |
C25—C24—C23 | 109.4 (11) | N4—C41—H41B | 108.6 |
C25—C24—H24 | 125.3 | C42—C41—H41B | 108.6 |
C23—C24—H24 | 125.3 | H41A—C41—H41B | 107.6 |
C24—C25—S21 | 112.7 (6) | O41—C42—C41 | 121.9 (2) |
C24—C25—H25 | 123.6 | O41—C42—C43 | 123.0 (3) |
S21—C25—H25 | 123.6 | C41—C42—C43 | 115.1 (2) |
C25—S21—C22 | 93.23 (16) | C42—C43—H43A | 109.5 |
C24'—C23'—H23' | 125.4 | C42—C43—H43B | 109.5 |
C25'—C24'—C23' | 110.5 (9) | H43A—C43—H43B | 109.5 |
C25'—C24'—H24' | 124.8 | C42—C43—H43C | 109.5 |
C23'—C24'—H24' | 124.8 | H43A—C43—H43C | 109.5 |
C24'—C25'—S21' | 114.3 (11) | H43B—C43—H43C | 109.5 |
C24'—C25'—H25' | 122.9 | C11—N12—N13 | 107.3 (3) |
S21'—C25'—H25' | 122.9 | C12—N13—N12 | 106.6 (3) |
N11—N1—C2 | 126.7 (2) | N13—C12—N11 | 110.2 (3) |
N11—N1—C5 | 121.8 (2) | N13—C12—H12 | 124.9 |
C2—N1—C5 | 109.8 (2) | N11—C12—H12 | 124.9 |
N3—C2—N1 | 109.6 (2) | N12—C11—N11 | 110.2 (3) |
N3—C2—C21 | 125.6 (3) | N12—C11—H11 | 124.9 |
N1—C2—C21 | 124.8 (2) | N11—C11—H11 | 124.9 |
C2—N3—N4 | 105.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C24'—H25···N12i | 1.08 | 2.57 | 3.593 (9) | 158 |
C25—H25···N12i | 0.93 | 2.57 | 3.409 (5) | 151 |
C41—H41A···N3ii | 0.97 | 2.53 | 3.495 (3) | 172 |
C41—H41B···O51iii | 0.97 | 2.47 | 3.217 (3) | 134 |
C43—H43A···O51iv | 0.96 | 2.56 | 3.426 (3) | 150 |
Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) −x, −y+1, −z+1; (iii) −x, −y+1, −z+2; (iv) −x+1, −y+1, −z+2. |
Experimental details
Crystal data | |
Chemical formula | C12H12N6O2S |
Mr | 304.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 5.8357 (8), 32.084 (4), 7.4958 (10) |
β (°) | 95.087 (3) |
V (Å3) | 1397.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.25 |
Crystal size (mm) | 0.37 × 0.30 × 0.13 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.685, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6559, 2412, 1214 |
Rint | 0.086 |
(sin θ/λ)max (Å−1) | 0.601 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.089, 0.82 |
No. of reflections | 2412 |
No. of parameters | 201 |
No. of restraints | 183 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.17 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
In a continuing search for pharmacologically active, 1,2,4-triazol and 1,2,4 triazol-5-one compounds it was found that most azole fungicides have been developed for diseases of cereal crops; examples include fluconazole (Ichikawa et al., 2001), ravuconazole (Ueda, 2003) and posaconazole (Kim et al., 2003). The properties of 1,2,4-triazole derivatives have broad-spectrum biological effects, such as insecticidal (Tsuda et al., 2004), herbicidal (Chai et al., 2003), anticonvulsant (Er-Rahimini & Mornet, 1992), antitumour (Nakip et al., 1994) and plant growth regulatory activities (Jenkins et al., 1989). Di- or tri-substituted 1,2,4-triazole derivatives have also been reported to show antituberculotic and antimicrobial activities (Demirbaş et al., 2004). Additionally, thermally stable polymers containing the 1, 2, 4-triazole moiety have been prepared (Shaikh et al., 2002).
The title compound (I)(Fig.1) consists of a triazole ring with an acetonyl group substituted at N4, a disordered (2,5-thienyl methyl) group substituted at C2, a 1,2,4-triazole ring substituted at N1 and an oxo O atom at C5. The N1—C5 bond length, 1.396 (3) Å, agrees with reported values [1.390 (3)Å in C13H13ClN4O2 (Çoruh, Kahveci, Şaşmaz, Aǧar, Kim & Erdönmez, 2003), 1.387 (3)Å in C12H11ClN4O2 (Çoruh, Kahveci, Şaşmaz, Aǧar & Kim, 2003)]. In the 1,2,4-triazole ring the N12—N13 bond length, 1.404 (4) Å, agrees with reported values [1.403 (8)Å in C19H18N6O2S (Sancak et al., 2005)].
The presence of a substituent on N4 causes a lengthening of the N—N bond length [N3—N4= 1.390 (3) Å] with respect to the corresponding bonds in 5-(2-chlorophenyl)-4-phenyl-3,4-dihydro-2H-1,2,4-triazole-3-thione [N—N= 1.374 (2) Å; Puviarasan et al., 1999] and in 4-methyl-1,2,4- triazole and 1-methyltetrazole [N—N= 1.344 (2) Å; Palmer & Parsons, 1996]. The S—C bond lengths [S21—C22= 1.681 (4)Å and S21—C25= 1.6807 Å] agree with values reported in the literature [S41—C44=1.676 (4)Å and S41—C41=1.689 (3)Å (Vrabel et al., 2005), C14—S1=1.692Å and C11—S1=1.708Å (Yılmaz et al., 2006)].
The thiophene ring is disordered over two positions, corresponding to rotation of approximately 180° about the single C21—C22 bond, with a major-minor ratio of about 50:50. Intermolecular hydrogen bonds are effective in stabilizing the crystal structure.