organic compounds
4-[(5-Chloro-2-hydroxybenzylidene)amino]-3-ethyl-1H-1,2,4-triazole-5(4H)-thione
aInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China, and bCollege of Chemistry & Chemical Engineering, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
*Correspondence e-mail: miaoli@sxu.edu.cn
The title compound, C11H11ClN4OS, crystallizes with two molecules, A and B, in the in which the dihedral angles between the triazole and benzene rings are 54.6 (3) and 56.0 (3)°. Both molecules feature an intramolecular O—H⋯N hydrogen bond, which generates an S(6) ring. In the crystal, A–B dimers are linked by pairs of weak C—H⋯S hydrogen bonds along with π–π stacking interactions between the triazole rings [centroid–centroid separations = 3.631 (3) and 3.981 (4)Å]. N—H⋯S hydrogen bonds link the dimers into [100] chains, which feature R22(8) loops.
CCDC reference: 997034
Related literature
For background to 1,2,4-triazoles fused to et al. (2013); Brandt et al. (2007). For related structures, see: Pannu et al. (2011); Wu et al. (2012).
see: SumangalaExperimental
Crystal data
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); 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.
Supporting information
CCDC reference: 997034
10.1107/S1600536814008320/hb7205sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814008320/hb7205Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814008320/hb7205Isup3.cml
0.5 mmol of 4-Amino-3-ethyl-1,2,4-triazole-5-thione was dissolved in 20 ml of ethanol with a constant stirring at 353 K. Then, 0.5 mmol of 5-chlorosalicylaldehyde in 10 ml of ethanol was added dropwise and the mixture solution was further refluxed for 2 h. The resulting yellow solution was filtered and the filtrate was left to stand at room temperature. The yellow blocks of the compound (I) were received from the filtrate with slowly evaporating solvent for a few days. Yield: 70%. Anal. Calcd. for C11H11ClN4OS: C 46.73, H 3.92, N 19.82%. Found: C 46.67, H 4.02, N 19.72%. IR (ν/cm-1): 3113, 3055, 2932, 1606, 1587, 1509, 1477, 1417, 1285, 1161, 1025, 965, 822, 657. UV/vis in DMSO, λmax/nm (ε 103/M-1 cm-1): 260(19.94), 342(8.14).
The H atoms bonded to C atoms were placed in calculated positions (C—H=0.96, 0.97 and 0.93 Å for Csp3, Csp2 and Csp atoms, respectively), assigned fixed Uiso values [Uiso H)=1.2 Ueq (Csp2) and 1.5Ueq (Csp3)] and treated as riding atoms. The H atoms attached to O and N atoms were found in the difference electron-density map and were refined isotropically, with O—H (0.82 Å) and N—H (0.86 Å) bond lengths.
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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).Fig. 1. The view of the structure of (I) with displacement ellipsoids drawn at the 30% probability level. Dotted lines indicate hydrogen bonds and π–π interactions. | |
Fig. 2. A part of the crystal structure I showing formation of a chain of R22(8) hydrogen-bonded rings and π–π stacking between Cg1 and Cg2 rings; Cg1: C1/C2/N1/N2/N3, Cg2: C12/C13/N5/N6/N7, Symmetry codes: i) x, y, z+1; ii) x, y, z-1. |
C11H11ClN4OS | F(000) = 584 |
Mr = 282.75 | Dx = 1.478 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1893 reflections |
a = 6.297 (3) Å | θ = 2.5–20.7° |
b = 16.418 (8) Å | µ = 0.46 mm−1 |
c = 12.290 (6) Å | T = 298 K |
β = 90.997 (7)° | Block, colorless |
V = 1270.2 (10) Å3 | 0.20 × 0.20 × 0.15 mm |
Z = 4 |
Bruker SMART APEX CCD diffractometer | 2451 independent reflections |
Radiation source: fine-focus sealed tube | 1924 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
ω scans | θmax = 25.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −7→7 |
Tmin = 0.914, Tmax = 0.935 | k = −19→19 |
14098 measured reflections | l = −14→14 |
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)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0375P)2 + 0.183P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2451 reflections | Δρmax = 0.17 e Å−3 |
329 parameters | Δρmin = −0.27 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 2274 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (10) |
C11H11ClN4OS | V = 1270.2 (10) Å3 |
Mr = 282.75 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.297 (3) Å | µ = 0.46 mm−1 |
b = 16.418 (8) Å | T = 298 K |
c = 12.290 (6) Å | 0.20 × 0.20 × 0.15 mm |
β = 90.997 (7)° |
Bruker SMART APEX CCD diffractometer | 2451 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 1924 reflections with I > 2σ(I) |
Tmin = 0.914, Tmax = 0.935 | Rint = 0.060 |
14098 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.084 | Δρmax = 0.17 e Å−3 |
S = 1.03 | Δρmin = −0.27 e Å−3 |
2451 reflections | Absolute structure: Flack (1983), 2274 Friedel pairs |
329 parameters | Absolute structure parameter: 0.03 (10) |
1 restraint |
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 | ||
Cl1 | 0.3625 (2) | 0.60813 (11) | 1.00331 (11) | 0.0760 (5) | |
N1 | 0.2557 (6) | 0.7267 (3) | 0.2890 (3) | 0.0444 (10) | |
H1 | 0.3494 | 0.7463 | 0.2461 | 0.053* | |
N2 | 0.0832 (7) | 0.6828 (3) | 0.2520 (3) | 0.0438 (11) | |
N3 | 0.0891 (6) | 0.6948 (3) | 0.4301 (3) | 0.0347 (10) | |
N4 | 0.0053 (6) | 0.6921 (3) | 0.5349 (3) | 0.0377 (10) | |
O1 | −0.2784 (6) | 0.7242 (3) | 0.6907 (3) | 0.0543 (11) | |
H1A | −0.2346 | 0.7258 | 0.6283 | 0.081* | |
S1 | 0.44562 (18) | 0.78763 (8) | 0.47087 (9) | 0.0436 (3) | |
C1 | 0.2662 (7) | 0.7364 (3) | 0.3962 (3) | 0.0364 (11) | |
C2 | −0.0177 (8) | 0.6646 (3) | 0.3409 (4) | 0.0377 (12) | |
C3 | −0.2158 (8) | 0.6175 (3) | 0.3463 (4) | 0.0453 (12) | |
H3A | −0.3226 | 0.6503 | 0.3816 | 0.054* | |
H3B | −0.1909 | 0.5695 | 0.3908 | 0.054* | |
C4 | −0.3003 (8) | 0.5911 (3) | 0.2359 (4) | 0.0518 (14) | |
H4A | −0.1964 | 0.5578 | 0.2009 | 0.078* | |
H4B | −0.3294 | 0.6383 | 0.1921 | 0.078* | |
H4C | −0.4287 | 0.5605 | 0.2447 | 0.078* | |
C5 | 0.1366 (8) | 0.6718 (3) | 0.6103 (4) | 0.0393 (13) | |
H5 | 0.2741 | 0.6570 | 0.5923 | 0.047* | |
C6 | 0.0756 (8) | 0.6715 (3) | 0.7232 (4) | 0.0368 (12) | |
C7 | −0.1230 (8) | 0.6988 (3) | 0.7578 (4) | 0.0411 (13) | |
C8 | −0.1660 (8) | 0.7003 (3) | 0.8684 (4) | 0.0523 (14) | |
H8 | −0.2956 | 0.7203 | 0.8918 | 0.063* | |
C9 | −0.0194 (9) | 0.6725 (4) | 0.9431 (4) | 0.0572 (15) | |
H9 | −0.0502 | 0.6730 | 1.0168 | 0.069* | |
C10 | 0.1759 (9) | 0.6436 (3) | 0.9084 (4) | 0.0497 (14) | |
C11 | 0.2243 (8) | 0.6449 (3) | 0.8005 (4) | 0.0456 (14) | |
H11 | 0.3576 | 0.6278 | 0.7785 | 0.055* | |
Cl2 | −0.3045 (2) | 0.97311 (11) | −0.41889 (11) | 0.0672 (5) | |
N5 | −0.2140 (6) | 0.8673 (3) | 0.2996 (3) | 0.0477 (11) | |
H5A | −0.3078 | 0.8485 | 0.3430 | 0.057* | |
N6 | −0.0421 (7) | 0.9120 (3) | 0.3347 (3) | 0.0471 (11) | |
N7 | −0.0462 (6) | 0.8961 (2) | 0.1579 (3) | 0.0360 (10) | |
N8 | 0.0415 (6) | 0.8959 (3) | 0.0537 (3) | 0.0404 (10) | |
O2 | 0.3237 (5) | 0.8558 (3) | −0.1000 (3) | 0.0567 (10) | |
H2 | 0.2853 | 0.8632 | −0.0374 | 0.085* | |
S2 | −0.40057 (19) | 0.80215 (8) | 0.11776 (9) | 0.0453 (3) | |
C12 | −0.2233 (7) | 0.8553 (3) | 0.1915 (4) | 0.0365 (11) | |
C13 | 0.0582 (8) | 0.9277 (3) | 0.2478 (4) | 0.0389 (12) | |
C14 | 0.2574 (8) | 0.9764 (4) | 0.2401 (4) | 0.0488 (13) | |
H14A | 0.2321 | 1.0232 | 0.1935 | 0.059* | |
H14B | 0.3670 | 0.9434 | 0.2075 | 0.059* | |
C15 | 0.3339 (9) | 1.0054 (3) | 0.3517 (4) | 0.0591 (15) | |
H15A | 0.3540 | 0.9593 | 0.3988 | 0.089* | |
H15B | 0.2298 | 1.0412 | 0.3820 | 0.089* | |
H15C | 0.4659 | 1.0340 | 0.3448 | 0.089* | |
C16 | −0.0890 (8) | 0.9128 (3) | −0.0232 (4) | 0.0376 (13) | |
H16 | −0.2273 | 0.9275 | −0.0064 | 0.045* | |
C17 | −0.0282 (8) | 0.9097 (3) | −0.1362 (4) | 0.0363 (12) | |
C18 | 0.1690 (8) | 0.8807 (3) | −0.1703 (4) | 0.0400 (12) | |
C19 | 0.2111 (8) | 0.8760 (3) | −0.2799 (4) | 0.0463 (14) | |
H19 | 0.3395 | 0.8542 | −0.3024 | 0.056* | |
C20 | 0.0655 (8) | 0.9030 (3) | −0.3562 (4) | 0.0440 (14) | |
H20 | 0.0955 | 0.8999 | −0.4299 | 0.053* | |
C21 | −0.1263 (9) | 0.9350 (3) | −0.3228 (4) | 0.0423 (13) | |
C22 | −0.1739 (8) | 0.9368 (3) | −0.2148 (4) | 0.0417 (13) | |
H22 | −0.3053 | 0.9563 | −0.1935 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0791 (11) | 0.1054 (14) | 0.0429 (8) | −0.0219 (10) | −0.0152 (7) | 0.0181 (8) |
N1 | 0.041 (2) | 0.065 (3) | 0.027 (2) | −0.005 (2) | 0.0082 (18) | 0.003 (2) |
N2 | 0.042 (3) | 0.061 (3) | 0.029 (2) | −0.002 (2) | 0.0026 (19) | −0.002 (2) |
N3 | 0.036 (2) | 0.044 (3) | 0.024 (2) | 0.000 (2) | 0.0078 (17) | 0.0003 (18) |
N4 | 0.040 (2) | 0.050 (3) | 0.024 (2) | 0.001 (2) | 0.0079 (18) | 0.0020 (19) |
O1 | 0.048 (2) | 0.078 (3) | 0.037 (2) | 0.010 (2) | 0.0084 (18) | 0.002 (2) |
S1 | 0.0429 (7) | 0.0589 (8) | 0.0293 (6) | −0.0055 (6) | 0.0057 (5) | −0.0008 (6) |
C1 | 0.038 (3) | 0.045 (3) | 0.026 (3) | 0.008 (2) | 0.007 (2) | 0.006 (2) |
C2 | 0.039 (3) | 0.041 (3) | 0.033 (3) | 0.009 (2) | 0.000 (2) | 0.000 (2) |
C3 | 0.046 (3) | 0.052 (3) | 0.039 (3) | 0.000 (3) | 0.005 (2) | −0.004 (2) |
C4 | 0.060 (3) | 0.046 (3) | 0.049 (3) | −0.007 (3) | −0.008 (3) | 0.000 (3) |
C5 | 0.043 (3) | 0.043 (3) | 0.032 (3) | −0.002 (2) | 0.009 (2) | 0.002 (2) |
C6 | 0.042 (3) | 0.041 (3) | 0.027 (3) | −0.006 (2) | 0.007 (2) | 0.001 (2) |
C7 | 0.049 (3) | 0.046 (3) | 0.029 (3) | −0.010 (3) | 0.010 (2) | −0.002 (2) |
C8 | 0.055 (3) | 0.066 (4) | 0.037 (3) | −0.005 (3) | 0.014 (3) | −0.004 (3) |
C9 | 0.069 (4) | 0.072 (4) | 0.031 (3) | −0.024 (3) | 0.017 (3) | −0.005 (3) |
C10 | 0.062 (4) | 0.060 (4) | 0.026 (3) | −0.021 (3) | −0.003 (2) | 0.004 (2) |
C11 | 0.048 (3) | 0.050 (3) | 0.039 (3) | −0.007 (3) | 0.007 (2) | −0.001 (3) |
Cl2 | 0.0642 (9) | 0.1033 (13) | 0.0339 (7) | 0.0065 (9) | −0.0054 (6) | 0.0041 (8) |
N5 | 0.045 (3) | 0.073 (3) | 0.025 (2) | −0.002 (2) | 0.0093 (19) | 0.002 (2) |
N6 | 0.045 (3) | 0.066 (3) | 0.030 (2) | 0.000 (2) | 0.003 (2) | −0.006 (2) |
N7 | 0.040 (2) | 0.048 (3) | 0.020 (2) | 0.006 (2) | 0.0032 (17) | 0.0036 (18) |
N8 | 0.044 (2) | 0.050 (3) | 0.027 (2) | 0.002 (2) | 0.0106 (19) | 0.0017 (19) |
O2 | 0.051 (2) | 0.082 (3) | 0.037 (2) | 0.018 (2) | 0.0077 (17) | 0.005 (2) |
S2 | 0.0447 (7) | 0.0605 (9) | 0.0308 (6) | −0.0031 (7) | 0.0049 (5) | 0.0026 (6) |
C12 | 0.036 (3) | 0.045 (3) | 0.029 (3) | 0.005 (2) | 0.005 (2) | 0.002 (2) |
C13 | 0.039 (3) | 0.050 (3) | 0.028 (3) | 0.008 (2) | 0.004 (2) | −0.004 (2) |
C14 | 0.052 (3) | 0.053 (3) | 0.042 (3) | 0.001 (3) | 0.006 (2) | −0.002 (3) |
C15 | 0.064 (4) | 0.058 (4) | 0.054 (3) | −0.014 (3) | −0.011 (3) | 0.001 (3) |
C16 | 0.041 (3) | 0.037 (3) | 0.034 (3) | 0.001 (2) | 0.009 (2) | 0.006 (2) |
C17 | 0.044 (3) | 0.034 (3) | 0.031 (3) | −0.009 (2) | 0.010 (2) | −0.002 (2) |
C18 | 0.045 (3) | 0.042 (3) | 0.034 (3) | 0.001 (2) | 0.007 (2) | 0.001 (2) |
C19 | 0.052 (3) | 0.048 (3) | 0.039 (3) | −0.004 (3) | 0.017 (3) | −0.008 (3) |
C20 | 0.056 (3) | 0.051 (3) | 0.025 (3) | −0.003 (3) | 0.011 (2) | −0.005 (2) |
C21 | 0.051 (3) | 0.047 (3) | 0.029 (3) | −0.005 (3) | −0.003 (2) | 0.002 (2) |
C22 | 0.040 (3) | 0.052 (3) | 0.034 (3) | 0.003 (2) | 0.005 (2) | 0.001 (2) |
Cl1—C10 | 1.741 (5) | Cl2—C21 | 1.732 (5) |
N1—C1 | 1.327 (6) | N5—C12 | 1.342 (6) |
N1—N2 | 1.375 (6) | N5—N6 | 1.371 (5) |
N1—H1 | 0.8600 | N5—H5A | 0.8600 |
N2—C2 | 1.308 (7) | N6—C13 | 1.277 (7) |
N3—C2 | 1.370 (6) | N7—C12 | 1.370 (6) |
N3—C1 | 1.378 (6) | N7—C13 | 1.377 (6) |
N3—N4 | 1.401 (5) | N7—N8 | 1.403 (5) |
N4—C5 | 1.275 (6) | N8—C16 | 1.272 (6) |
O1—C7 | 1.335 (6) | O2—C18 | 1.355 (5) |
O1—H1A | 0.8200 | O2—H2 | 0.8200 |
S1—C1 | 1.670 (5) | S2—C12 | 1.672 (5) |
C2—C3 | 1.470 (7) | C13—C14 | 1.492 (7) |
C3—C4 | 1.512 (6) | C14—C15 | 1.522 (6) |
C3—H3A | 0.9700 | C14—H14A | 0.9700 |
C3—H3B | 0.9700 | C14—H14B | 0.9700 |
C4—H4A | 0.9600 | C15—H15A | 0.9600 |
C4—H4B | 0.9600 | C15—H15B | 0.9600 |
C4—H4C | 0.9600 | C15—H15C | 0.9600 |
C5—C6 | 1.446 (6) | C16—C17 | 1.448 (7) |
C5—H5 | 0.9300 | C16—H16 | 0.9300 |
C6—C11 | 1.392 (7) | C17—C22 | 1.394 (7) |
C6—C7 | 1.402 (7) | C17—C18 | 1.400 (7) |
C7—C8 | 1.390 (6) | C18—C19 | 1.380 (7) |
C8—C9 | 1.369 (7) | C19—C20 | 1.373 (7) |
C8—H8 | 0.9300 | C19—H19 | 0.9300 |
C9—C10 | 1.392 (8) | C20—C21 | 1.386 (7) |
C9—H9 | 0.9300 | C20—H20 | 0.9300 |
C10—C11 | 1.366 (6) | C21—C22 | 1.366 (7) |
C11—H11 | 0.9300 | C22—H22 | 0.9300 |
C1—N1—N2 | 114.6 (4) | C12—N5—N6 | 114.2 (4) |
C1—N1—H1 | 122.7 | C12—N5—H5A | 122.9 |
N2—N1—H1 | 122.7 | N6—N5—H5A | 122.9 |
C2—N2—N1 | 103.7 (4) | C13—N6—N5 | 104.2 (4) |
C2—N3—C1 | 109.0 (4) | C12—N7—C13 | 108.8 (4) |
C2—N3—N4 | 122.5 (4) | C12—N7—N8 | 127.5 (4) |
C1—N3—N4 | 127.8 (4) | C13—N7—N8 | 122.8 (4) |
C5—N4—N3 | 115.2 (4) | C16—N8—N7 | 114.8 (4) |
C7—O1—H1A | 109.5 | C18—O2—H2 | 109.5 |
N1—C1—N3 | 102.4 (4) | N5—C12—N7 | 101.8 (4) |
N1—C1—S1 | 128.8 (4) | N5—C12—S2 | 129.0 (4) |
N3—C1—S1 | 128.8 (3) | N7—C12—S2 | 129.1 (3) |
N2—C2—N3 | 110.3 (4) | N6—C13—N7 | 111.0 (5) |
N2—C2—C3 | 125.7 (4) | N6—C13—C14 | 126.2 (5) |
N3—C2—C3 | 124.0 (4) | N7—C13—C14 | 122.8 (4) |
C2—C3—C4 | 113.3 (4) | C13—C14—C15 | 111.3 (4) |
C2—C3—H3A | 108.9 | C13—C14—H14A | 109.4 |
C4—C3—H3A | 108.9 | C15—C14—H14A | 109.4 |
C2—C3—H3B | 108.9 | C13—C14—H14B | 109.4 |
C4—C3—H3B | 108.9 | C15—C14—H14B | 109.4 |
H3A—C3—H3B | 107.7 | H14A—C14—H14B | 108.0 |
C3—C4—H4A | 109.5 | C14—C15—H15A | 109.5 |
C3—C4—H4B | 109.5 | C14—C15—H15B | 109.5 |
H4A—C4—H4B | 109.5 | H15A—C15—H15B | 109.5 |
C3—C4—H4C | 109.5 | C14—C15—H15C | 109.5 |
H4A—C4—H4C | 109.5 | H15A—C15—H15C | 109.5 |
H4B—C4—H4C | 109.5 | H15B—C15—H15C | 109.5 |
N4—C5—C6 | 121.2 (5) | N8—C16—C17 | 121.8 (5) |
N4—C5—H5 | 119.4 | N8—C16—H16 | 119.1 |
C6—C5—H5 | 119.4 | C17—C16—H16 | 119.1 |
C11—C6—C7 | 119.0 (4) | C22—C17—C18 | 118.5 (5) |
C11—C6—C5 | 118.0 (5) | C22—C17—C16 | 118.2 (5) |
C7—C6—C5 | 122.9 (5) | C18—C17—C16 | 123.4 (5) |
O1—C7—C8 | 116.4 (4) | O2—C18—C19 | 117.2 (4) |
O1—C7—C6 | 124.1 (4) | O2—C18—C17 | 122.9 (4) |
C8—C7—C6 | 119.5 (5) | C19—C18—C17 | 119.9 (5) |
C9—C8—C7 | 120.6 (5) | C20—C19—C18 | 120.7 (5) |
C9—C8—H8 | 119.7 | C20—C19—H19 | 119.7 |
C7—C8—H8 | 119.7 | C18—C19—H19 | 119.7 |
C8—C9—C10 | 119.8 (5) | C19—C20—C21 | 119.7 (5) |
C8—C9—H9 | 120.1 | C19—C20—H20 | 120.1 |
C10—C9—H9 | 120.1 | C21—C20—H20 | 120.1 |
C11—C10—C9 | 120.4 (5) | C22—C21—C20 | 120.2 (5) |
C11—C10—Cl1 | 119.8 (4) | C22—C21—Cl2 | 120.3 (4) |
C9—C10—Cl1 | 119.9 (4) | C20—C21—Cl2 | 119.5 (4) |
C10—C11—C6 | 120.6 (5) | C21—C22—C17 | 120.9 (5) |
C10—C11—H11 | 119.7 | C21—C22—H22 | 119.5 |
C6—C11—H11 | 119.7 | C17—C22—H22 | 119.5 |
C1—N1—N2—C2 | 0.1 (6) | C12—N5—N6—C13 | −0.4 (6) |
C2—N3—N4—C5 | 137.3 (5) | C12—N7—N8—C16 | 52.0 (6) |
C1—N3—N4—C5 | −53.0 (7) | C13—N7—N8—C16 | −139.5 (5) |
N2—N1—C1—N3 | 0.8 (5) | N6—N5—C12—N7 | −0.6 (5) |
N2—N1—C1—S1 | −178.1 (4) | N6—N5—C12—S2 | 177.7 (4) |
C2—N3—C1—N1 | −1.3 (5) | C13—N7—C12—N5 | 1.3 (5) |
N4—N3—C1—N1 | −172.1 (4) | N8—N7—C12—N5 | 171.1 (4) |
C2—N3—C1—S1 | 177.6 (4) | C13—N7—C12—S2 | −177.0 (4) |
N4—N3—C1—S1 | 6.8 (7) | N8—N7—C12—S2 | −7.2 (7) |
N1—N2—C2—N3 | −0.9 (5) | N5—N6—C13—N7 | 1.3 (5) |
N1—N2—C2—C3 | 180.0 (5) | N5—N6—C13—C14 | 179.0 (5) |
C1—N3—C2—N2 | 1.5 (6) | C12—N7—C13—N6 | −1.7 (6) |
N4—N3—C2—N2 | 172.8 (4) | N8—N7—C13—N6 | −172.1 (4) |
C1—N3—C2—C3 | −179.4 (5) | C12—N7—C13—C14 | −179.5 (5) |
N4—N3—C2—C3 | −8.0 (7) | N8—N7—C13—C14 | 10.1 (7) |
N2—C2—C3—C4 | −0.8 (7) | N6—C13—C14—C15 | 0.9 (8) |
N3—C2—C3—C4 | −179.8 (5) | N7—C13—C14—C15 | 178.4 (4) |
N3—N4—C5—C6 | 176.1 (4) | N7—N8—C16—C17 | −175.6 (4) |
N4—C5—C6—C11 | 177.0 (5) | N8—C16—C17—C22 | −173.7 (5) |
N4—C5—C6—C7 | −4.9 (8) | N8—C16—C17—C18 | 6.4 (8) |
C11—C6—C7—O1 | −178.7 (5) | C22—C17—C18—O2 | 177.7 (5) |
C5—C6—C7—O1 | 3.2 (8) | C16—C17—C18—O2 | −2.5 (8) |
C11—C6—C7—C8 | 1.2 (8) | C22—C17—C18—C19 | −3.0 (8) |
C5—C6—C7—C8 | −176.9 (5) | C16—C17—C18—C19 | 176.8 (5) |
O1—C7—C8—C9 | 177.5 (5) | O2—C18—C19—C20 | −177.5 (5) |
C6—C7—C8—C9 | −2.4 (8) | C17—C18—C19—C20 | 3.2 (8) |
C7—C8—C9—C10 | 0.9 (9) | C18—C19—C20—C21 | −0.4 (8) |
C8—C9—C10—C11 | 1.8 (8) | C19—C20—C21—C22 | −2.5 (8) |
C8—C9—C10—Cl1 | −179.9 (4) | C19—C20—C21—Cl2 | 177.2 (4) |
C9—C10—C11—C6 | −3.0 (8) | C20—C21—C22—C17 | 2.6 (8) |
Cl1—C10—C11—C6 | 178.7 (4) | Cl2—C21—C22—C17 | −177.1 (4) |
C7—C6—C11—C10 | 1.5 (8) | C18—C17—C22—C21 | 0.2 (8) |
C5—C6—C11—C10 | 179.7 (5) | C16—C17—C22—C21 | −179.7 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S2i | 0.86 | 2.43 | 3.287 (4) | 177 |
N5—H5A···S1ii | 0.86 | 2.44 | 3.300 (4) | 176 |
O1—H1A···N4 | 0.82 | 1.99 | 2.693 (5) | 143 |
O2—H2···N8 | 0.82 | 1.99 | 2.699 (5) | 144 |
C15—H15A···S1 | 0.96 | 3.01 | 3.922 (6) | 160 |
C4—H4B···S2 | 0.96 | 2.87 | 3.805 (6) | 164 |
Cg1···Cg2 | 3.631 (3) | |||
Cg3···Cg4iii | 3.981 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, y, z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···S2i | 0.86 | 2.43 | 3.287 (4) | 177 |
N5—H5A···S1ii | 0.86 | 2.44 | 3.300 (4) | 176 |
O1—H1A···N4 | 0.82 | 1.99 | 2.693 (5) | 143 |
O2—H2···N8 | 0.82 | 1.99 | 2.699 (5) | 144 |
C15—H15A···S1 | 0.96 | 3.01 | 3.922 (6) | 160 |
C4—H4B···S2 | 0.96 | 2.87 | 3.805 (6) | 164 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Acknowledgements
The authors acknowledge the National Natural Science Foundation of China (grant Nos. 21001070 and 21271121), the Provincial Natural Science Foundation of Shanxi Province of China (grant No. 2011021006–2), the Shanxi Scholarship Council of China (2013–026) and the Student Innovative and Entrepreneurship Training Program of Shanxi Province (2013B29 and 2013011057) as well as the Colleges and Universities in Shanxi Province Science and Technology Research and Development Project (20111002) for financial support.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The incorporation of the 1,2,4-triazole unit into Schiff base is of considerable current interest as complexes of 1,2,4-triazoles which are being developed for potential use in pharmaceutical and material applications (Sumangala et al. 2013; Brandt et al. 2007). Therefore, the title compound (I), has been synthesized and its crystal structure has been determinated.
The crystal structure is illustrated in Fig. 1 and the main geometric parameters of the commpound are listed in Table 1. The title compound (I) crystallizes in the monoclinic space group P21 with two symmetry-independent molecules in the unit cell. The bond lengths of N4—C5 (1.275 Å) and N8—C16 (1.272 Å) confirm them as double bonds, which is similar to those reported in other Schiff bases (Pannu et al. 2011; Wu et al. 2012;). It is noticeable that the C—S bond length (1.670 Å) in the compound is close to C═S double bond, indicating that the compound exists in the thione form.
The packing arrangement in the crystal structure of (I) is shown in Fig. 2. As is a common feature of o-hydroxysalicylidene systems, the compound displays the strong intermolecular and intramolecular hydrogen bond between atoms N, O and S. The molecules of the compound is linked by an inversion-related pair of almost linear intermolecular hydrogen bonds N—H···S to form the cyclic centrosymmetric dimers characterized by an R22(8) motif. The dimer is further held together by the π–π interactions between two rings (Cg1 and Cg2) in the crystal.