(E)-4-(2-Chloro­benzyl­ideneamino)-3-(2-chloro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione–(E)-1,5-bis­(2-chloro­benzyl­idene)thio­carbonohydrazide–methanol (1/1/1)

Guo, Q.

doi:10.1107/S1600536809053203

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o141

doi:10.1107/S1600536809053203

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(E)-4-(2-Chlorobenzylideneamino)-3-(2-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione–(E)-1,5-bis(2-chlorobenzylidene)thiocarbonohydrazide–methanol (1/1/1)

Qingliang Guo ^a ^*

^aDepartment of Chemistry and Environmental Science, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: jingtixuebao@163.com

(Received 7 December 2009; accepted 10 December 2009; online 16 December 2009)

In the title compound, C₁₅H₁₂Cl₂N₄S·C₁₅H₁₀Cl₂N₄S·C₂H₆O, the two chlorophenyl rings of the triazole derivative form dihedral angles of 65.7 (2) and 44.2 (2)° with the triazole ring. In the thiocarbonohydrazide derivative, the dihedral angle between the two chlorophenyl rings is 5.4 (2)°. In the crystal, the triazole, thiocarbonohydrazide and methanol molecules are linked by N—H⋯O, N—H⋯S and O—H⋯S hydrogen bonds, forming a hexameric unit.

Related literature

For general background to Schiff bases, see: Ren et al. (1999 ); Yang et al. (2005 ); Sen et al. (1998 ); Xia et al. (2007 ). For the biological activity of Schiff bases, see: Liang (2003 ); Bacci et al. (2005 ).

Experimental

Crystal data

C₁₅H₁₀Cl₂N₄S·C₁₅H₁₂Cl₂N₄S·C₂H₆O
M_r = 746.54
Triclinic, $[P \overline 1]$
a = 7.7086 (6) Å
b = 10.9999 (9) Å
c = 20.9827 (16) Å
α = 94.678 (1)°
β = 92.083 (1)°
γ = 99.851 (1)°
V = 1744.8 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 293 K
0.35 × 0.26 × 0.23 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.845, T_max = 0.894
9324 measured reflections
6154 independent reflections
3724 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.111
S = 1.01
6154 reflections
425 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1	0.86	2.20	2.978 (4)	150
N6—H6⋯S1ⁱ	0.86	2.41	3.261 (3)	170
N3—H3⋯S2ⁱⁱ	0.86	2.56	3.410 (2)	169
O1—H1⋯S1ⁱⁱⁱ	0.82	2.65	3.413 (3)	156
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) -x, -y+2, -z+1.

Data collection: SMART (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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053203/ci2984sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809053203/ci2984Isup2.hkl

checkCIF report

Comment top

The synthesis and structural investigation of Schiff base compounds have attracted much attention due to their interesting structures and potential applications. Some of them have biological activities (Liang, 2003; Bacci et al., 2005). They also play an important role in the development of coordination chemistry as well as inorganic biochemistry, catalysis and optical materials (Ren et al., 1999; Yang et al. 2005; Sen et al. 1998).

The triazole ring forms dihedral angles of 65.7 (2) and 44.2 (2)°, respectively, with the C16-C21 and C25-C30 rings. The dihedral angle between the C1-C6 and C10-C15 rings is 5.4 (2)°. Two triazole, two thiocarbonohydrazide and two methanol molecules are linked by N—H···O, N—H···S and O—H···S hydrogen bonds to form a hexamer.

Related literature top

For general background to Schiff bases, see: Ren et al. (1999); Yang et al. (2005); Sen et al. (1998); Xia et al. (2007). For the biological activity of Schiff bases, see: Liang (2003); Bacci et al. (2005).

Experimental top

The Schiff base compound was synthesized according to the modified method of Xia et al. (2007). A mixture of (2-chlorophenyl)methanamine and thiourea in methanol (30 ml) was refluxed for 3 h and filtered. The filtrate was placed for sevaral days yielding colourless block-shaped crystals. (yield 79%). Elemental analysis: Calculated for C₃₂H₂₈Cl₄N₈OS₂: C 51.48, H 3.78, N 15.01; found: C 51.51, H 3.49, N 15.13.

Computing details top

Data collection: SMART (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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. H atoms have been omitted for clarity.

(E)-4-(2-Chlorobenzylideneamino)-3-(2-chlorophenyl)-1H-1,2,4- triazole-5(4H)-thione–(E)-1,5-bis(2- chlorobenzylidene)thiocarbonohydrazide–methanol (1/1/1) top

Crystal data top

C₁₅H₁₀Cl₂N₄S·C₁₅H₁₂Cl₂N₄S·C₂H₆O	Z = 2
M_r = 746.54	F(000) = 768
Triclinic, P1	D_x = 1.421 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7086 (6) Å	Cell parameters from 1667 reflections
b = 10.9999 (9) Å	θ = 2.2–20.5°
c = 20.9827 (16) Å	µ = 0.50 mm⁻¹
α = 94.678 (1)°	T = 293 K
β = 92.083 (1)°	Block, colourless
γ = 99.851 (1)°	0.35 × 0.26 × 0.23 mm
V = 1744.8 (2) Å³

Data collection top

Bruker SMART APEX diffractometer	6154 independent reflections
Radiation source: fine-focus sealed tube	3724 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 25.1°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→9
T_min = 0.845, T_max = 0.894	k = −12→13
9324 measured reflections	l = −24→24

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0365P)² + 0.4564P] where P = (F_o² + 2F_c²)/3
6154 reflections	(Δ/σ)_max = 0.001
425 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₅H₁₀Cl₂N₄S·C₁₅H₁₂Cl₂N₄S·C₂H₆O	γ = 99.851 (1)°
M_r = 746.54	V = 1744.8 (2) Å³
Triclinic, P1	Z = 2
a = 7.7086 (6) Å	Mo Kα radiation
b = 10.9999 (9) Å	µ = 0.50 mm⁻¹
c = 20.9827 (16) Å	T = 293 K
α = 94.678 (1)°	0.35 × 0.26 × 0.23 mm
β = 92.083 (1)°

Data collection top

Bruker SMART APEX diffractometer	6154 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3724 reflections with I > 2σ(I)
T_min = 0.845, T_max = 0.894	R_int = 0.026
9324 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.01	Δρ_max = 0.28 e Å⁻³
6154 reflections	Δρ_min = −0.25 e Å⁻³
425 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
S1	0.25610 (13)	1.26698 (8)	0.43362 (4)	0.0574 (3)
S2	0.40630 (12)	0.14705 (9)	0.24096 (4)	0.0614 (3)
Cl1	0.15231 (15)	0.94451 (10)	0.71997 (4)	0.0836 (3)
Cl2	0.48468 (13)	0.77336 (9)	0.21104 (4)	0.0738 (3)
Cl3	0.21316 (12)	0.52305 (8)	0.10925 (5)	0.0689 (3)
Cl4	0.22413 (15)	−0.15631 (9)	0.07317 (5)	0.0861 (3)
O1	0.1682 (4)	0.7954 (3)	0.52080 (14)	0.0837 (8)
H1	0.0608	0.7901	0.5211	0.126*
N1	0.1820 (3)	1.1229 (2)	0.54344 (12)	0.0487 (7)
N2	0.2441 (3)	1.0597 (2)	0.49247 (11)	0.0472 (7)
H2	0.2608	0.9847	0.4944	0.057*
N3	0.3341 (3)	1.0539 (2)	0.39024 (11)	0.0506 (7)
H3	0.3534	1.0877	0.3550	0.061*
N4	0.3618 (3)	0.9349 (2)	0.39441 (11)	0.0468 (6)
N5	0.0553 (4)	0.3611 (2)	0.26242 (12)	0.0529 (7)
N6	0.1796 (3)	0.2949 (2)	0.28209 (11)	0.0542 (7)
H6	0.2121	0.2943	0.3217	0.065*
N7	0.1565 (3)	0.2589 (2)	0.18135 (11)	0.0459 (6)
N8	0.1743 (3)	0.2251 (2)	0.11665 (11)	0.0463 (6)
C1	0.0902 (4)	1.0862 (3)	0.70951 (15)	0.0566 (9)
C2	0.1044 (4)	1.1357 (3)	0.65067 (14)	0.0463 (8)
C3	0.0605 (4)	1.2523 (3)	0.64682 (16)	0.0607 (9)
H3A	0.0690	1.2880	0.6081	0.073*
C4	0.0045 (5)	1.3162 (4)	0.6992 (2)	0.0762 (11)
H4	−0.0224	1.3948	0.6960	0.091*
C5	−0.0114 (5)	1.2632 (5)	0.7562 (2)	0.0841 (13)
H5	−0.0512	1.3057	0.7913	0.101*
C6	0.0306 (5)	1.1495 (4)	0.76173 (17)	0.0767 (12)
H6A	0.0192	1.1141	0.8005	0.092*
C7	0.1671 (4)	1.0702 (3)	0.59493 (14)	0.0480 (8)
H7	0.1953	0.9918	0.5973	0.058*
C8	0.2777 (4)	1.1187 (3)	0.43966 (14)	0.0434 (7)
C9	0.4020 (4)	0.8808 (3)	0.34211 (15)	0.0499 (8)
H9	0.4075	0.9231	0.3054	0.060*
C10	0.4389 (4)	0.7564 (3)	0.33816 (14)	0.0455 (8)
C11	0.4785 (4)	0.6972 (3)	0.28059 (15)	0.0515 (8)
C12	0.5155 (5)	0.5792 (3)	0.27706 (19)	0.0674 (10)
H12	0.5434	0.5420	0.2383	0.081*
C13	0.5112 (5)	0.5166 (4)	0.3307 (2)	0.0785 (12)
H13	0.5351	0.4364	0.3283	0.094*
C14	0.4719 (5)	0.5714 (3)	0.3881 (2)	0.0758 (11)
H14	0.4688	0.5284	0.4245	0.091*
C15	0.4369 (4)	0.6898 (3)	0.39182 (16)	0.0596 (9)
H15	0.4114	0.7265	0.4311	0.072*
C16	−0.0109 (4)	0.4711 (3)	0.11266 (15)	0.0498 (8)
C17	−0.0726 (4)	0.3890 (3)	0.15659 (14)	0.0444 (8)
C18	−0.2529 (5)	0.3556 (3)	0.16078 (16)	0.0599 (9)
H18	−0.2967	0.3019	0.1907	0.072*
C19	−0.3681 (5)	0.4010 (4)	0.12104 (19)	0.0719 (11)
H19	−0.4891	0.3765	0.1235	0.086*
C20	−0.3039 (6)	0.4819 (4)	0.07809 (18)	0.0759 (12)
H20	−0.3819	0.5130	0.0516	0.091*
C21	−0.1245 (5)	0.5180 (3)	0.07351 (16)	0.0667 (10)
H21	−0.0814	0.5735	0.0443	0.080*
C22	0.0461 (4)	0.3399 (3)	0.20069 (14)	0.0443 (8)
C23	0.2465 (4)	0.2311 (3)	0.23466 (14)	0.0460 (8)
C24	0.2022 (4)	0.1161 (3)	0.10273 (14)	0.0486 (8)
H24	0.2049	0.0624	0.1346	0.058*
C25	0.2301 (4)	0.0749 (3)	0.03672 (14)	0.0479 (8)
C26	0.2425 (4)	−0.0464 (3)	0.01809 (15)	0.0561 (9)
C27	0.2720 (5)	−0.0836 (4)	−0.0444 (2)	0.0790 (12)
H27	0.2803	−0.1657	−0.0561	0.095*
C28	0.2890 (6)	0.0012 (5)	−0.08861 (19)	0.0903 (14)
H28	0.3108	−0.0233	−0.1306	0.108*
C29	0.2744 (6)	0.1223 (5)	−0.07193 (18)	0.0872 (13)
H29	0.2839	0.1789	−0.1027	0.105*
C30	0.2458 (5)	0.1594 (3)	−0.00994 (15)	0.0651 (10)
H30	0.2366	0.2415	0.0013	0.078*
C31	0.1607 (8)	0.5962 (6)	0.5595 (4)	0.192 (4)
H31A	0.0341	0.5822	0.5574	0.288*
H31B	0.2023	0.5618	0.5966	0.288*
H31C	0.2014	0.5572	0.5217	0.288*
C32	0.2229 (7)	0.7192 (6)	0.5636 (3)	0.137 (2)
H32A	0.3501	0.7290	0.5621	0.164*
H32B	0.1986	0.7524	0.6060	0.164*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0842 (7)	0.0466 (5)	0.0462 (5)	0.0223 (5)	0.0086 (4)	0.0072 (4)
S2	0.0711 (6)	0.0711 (6)	0.0526 (5)	0.0330 (5)	0.0123 (5)	0.0211 (5)
Cl1	0.1144 (9)	0.0774 (7)	0.0609 (6)	0.0123 (6)	0.0128 (6)	0.0226 (5)
Cl2	0.0862 (7)	0.0867 (7)	0.0473 (5)	0.0142 (6)	0.0118 (5)	−0.0027 (5)
Cl3	0.0576 (6)	0.0654 (6)	0.0864 (7)	0.0088 (5)	0.0044 (5)	0.0266 (5)
Cl4	0.1162 (9)	0.0531 (6)	0.0935 (8)	0.0272 (6)	0.0055 (6)	0.0064 (5)
O1	0.086 (2)	0.0733 (18)	0.099 (2)	0.0229 (17)	0.0189 (17)	0.0211 (16)
N1	0.0572 (18)	0.0483 (16)	0.0421 (15)	0.0134 (13)	0.0085 (13)	0.0011 (13)
N2	0.0617 (18)	0.0441 (15)	0.0402 (14)	0.0176 (13)	0.0103 (13)	0.0080 (12)
N3	0.0725 (19)	0.0443 (16)	0.0391 (14)	0.0180 (14)	0.0112 (13)	0.0080 (12)
N4	0.0585 (18)	0.0404 (15)	0.0442 (15)	0.0139 (13)	0.0096 (13)	0.0052 (12)
N5	0.071 (2)	0.0499 (17)	0.0428 (15)	0.0239 (15)	0.0053 (14)	0.0018 (13)
N6	0.073 (2)	0.0553 (17)	0.0381 (15)	0.0198 (15)	0.0002 (14)	0.0066 (13)
N7	0.0568 (17)	0.0475 (16)	0.0378 (14)	0.0186 (13)	0.0076 (13)	0.0071 (12)
N8	0.0552 (17)	0.0499 (17)	0.0374 (14)	0.0180 (13)	0.0080 (12)	0.0049 (12)
C1	0.049 (2)	0.070 (2)	0.0462 (19)	0.0005 (18)	0.0070 (16)	−0.0004 (18)
C2	0.0424 (19)	0.050 (2)	0.0436 (18)	0.0020 (16)	0.0050 (15)	−0.0025 (16)
C3	0.059 (2)	0.066 (2)	0.056 (2)	0.0138 (19)	0.0020 (18)	−0.0050 (19)
C4	0.069 (3)	0.074 (3)	0.084 (3)	0.021 (2)	0.003 (2)	−0.021 (2)
C5	0.072 (3)	0.108 (4)	0.068 (3)	0.016 (3)	0.019 (2)	−0.027 (3)
C6	0.077 (3)	0.101 (3)	0.046 (2)	0.002 (3)	0.016 (2)	−0.005 (2)
C7	0.052 (2)	0.0485 (19)	0.0436 (18)	0.0088 (16)	0.0053 (15)	0.0021 (16)
C8	0.0454 (19)	0.0458 (19)	0.0402 (17)	0.0115 (15)	0.0025 (14)	0.0045 (15)
C9	0.059 (2)	0.047 (2)	0.0444 (18)	0.0098 (17)	0.0050 (16)	0.0072 (16)
C10	0.047 (2)	0.0381 (18)	0.0503 (19)	0.0071 (15)	0.0035 (15)	−0.0002 (15)
C11	0.045 (2)	0.053 (2)	0.055 (2)	0.0086 (16)	−0.0013 (16)	−0.0042 (17)
C12	0.065 (3)	0.058 (2)	0.077 (3)	0.016 (2)	0.001 (2)	−0.017 (2)
C13	0.081 (3)	0.048 (2)	0.107 (3)	0.021 (2)	−0.008 (3)	−0.004 (2)
C14	0.092 (3)	0.054 (2)	0.083 (3)	0.019 (2)	−0.007 (2)	0.013 (2)
C15	0.070 (3)	0.049 (2)	0.061 (2)	0.0120 (18)	0.0052 (19)	0.0037 (18)
C16	0.050 (2)	0.050 (2)	0.0506 (19)	0.0145 (16)	−0.0002 (16)	−0.0009 (16)
C17	0.055 (2)	0.0372 (17)	0.0430 (17)	0.0168 (16)	0.0058 (15)	−0.0046 (14)
C18	0.060 (2)	0.059 (2)	0.063 (2)	0.0171 (19)	0.0163 (19)	−0.0038 (18)
C19	0.052 (2)	0.081 (3)	0.084 (3)	0.023 (2)	0.003 (2)	−0.007 (2)
C20	0.071 (3)	0.096 (3)	0.069 (3)	0.042 (3)	−0.009 (2)	0.003 (2)
C21	0.072 (3)	0.078 (3)	0.058 (2)	0.031 (2)	0.002 (2)	0.018 (2)
C22	0.052 (2)	0.0393 (18)	0.0441 (18)	0.0124 (15)	0.0102 (15)	0.0049 (15)
C23	0.057 (2)	0.0432 (18)	0.0390 (17)	0.0106 (16)	0.0048 (15)	0.0058 (15)
C24	0.060 (2)	0.047 (2)	0.0419 (18)	0.0171 (17)	0.0053 (16)	0.0078 (15)
C25	0.049 (2)	0.055 (2)	0.0431 (18)	0.0173 (16)	0.0067 (15)	0.0044 (16)
C26	0.056 (2)	0.059 (2)	0.054 (2)	0.0198 (18)	−0.0012 (17)	−0.0064 (18)
C27	0.081 (3)	0.083 (3)	0.073 (3)	0.030 (2)	0.003 (2)	−0.025 (2)
C28	0.092 (3)	0.130 (4)	0.048 (2)	0.031 (3)	0.006 (2)	−0.023 (3)
C29	0.106 (4)	0.114 (4)	0.048 (2)	0.030 (3)	0.021 (2)	0.015 (2)
C30	0.078 (3)	0.073 (3)	0.051 (2)	0.027 (2)	0.0156 (19)	0.0117 (19)
C31	0.122 (5)	0.109 (5)	0.359 (11)	0.040 (4)	−0.016 (6)	0.079 (6)
C32	0.084 (4)	0.125 (5)	0.211 (7)	0.027 (4)	−0.004 (4)	0.056 (5)

Geometric parameters (Å, º) top

S1—C8	1.682 (3)	C10—C11	1.394 (4)
S2—C23	1.669 (3)	C11—C12	1.373 (4)
Cl1—C1	1.735 (4)	C12—C13	1.364 (5)
Cl2—C11	1.739 (3)	C12—H12	0.93
Cl3—C16	1.730 (3)	C13—C14	1.370 (5)
Cl4—C26	1.732 (3)	C13—H13	0.93
O1—C32	1.380 (5)	C14—C15	1.371 (4)
O1—H1	0.82	C14—H14	0.93
N1—C7	1.267 (3)	C15—H15	0.93
N1—N2	1.373 (3)	C16—C21	1.371 (4)
N2—C8	1.341 (3)	C16—C17	1.383 (4)
N2—H2	0.86	C17—C18	1.383 (4)
N3—C8	1.338 (3)	C17—C22	1.474 (4)
N3—N4	1.372 (3)	C18—C19	1.378 (5)
N3—H3	0.86	C18—H18	0.93
N4—C9	1.279 (3)	C19—C20	1.365 (5)
N5—C22	1.294 (3)	C19—H19	0.93
N5—N6	1.370 (3)	C20—C21	1.381 (5)
N6—C23	1.340 (3)	C20—H20	0.93
N6—H6	0.86	C21—H21	0.93
N7—C23	1.378 (3)	C24—C25	1.457 (4)
N7—C22	1.382 (3)	C24—H24	0.93
N7—N8	1.396 (3)	C25—C26	1.380 (4)
N8—C24	1.267 (3)	C25—C30	1.398 (4)
C1—C6	1.385 (4)	C26—C27	1.379 (5)
C1—C2	1.389 (4)	C27—C28	1.363 (5)
C2—C3	1.390 (4)	C27—H27	0.93
C2—C7	1.463 (4)	C28—C29	1.374 (6)
C3—C4	1.379 (4)	C28—H28	0.93
C3—H3A	0.93	C29—C30	1.368 (5)
C4—C5	1.372 (5)	C29—H29	0.93
C4—H4	0.93	C30—H30	0.93
C5—C6	1.358 (5)	C31—C32	1.350 (7)
C5—H5	0.93	C31—H31A	0.96
C6—H6A	0.93	C31—H31B	0.96
C7—H7	0.93	C31—H31C	0.96
C9—C10	1.441 (4)	C32—H32A	0.97
C9—H9	0.93	C32—H32B	0.97
C10—C15	1.391 (4)

C32—O1—H1	109.5	C14—C15—H15	119.3
C7—N1—N2	116.9 (2)	C10—C15—H15	119.3
C8—N2—N1	117.8 (2)	C21—C16—C17	121.3 (3)
C8—N2—H2	121.1	C21—C16—Cl3	118.6 (3)
N1—N2—H2	121.1	C17—C16—Cl3	120.0 (2)
C8—N3—N4	121.6 (2)	C16—C17—C18	118.5 (3)
C8—N3—H3	119.2	C16—C17—C22	122.6 (3)
N4—N3—H3	119.2	C18—C17—C22	118.9 (3)
C9—N4—N3	114.8 (2)	C19—C18—C17	120.7 (3)
C22—N5—N6	103.9 (2)	C19—C18—H18	119.7
C23—N6—N5	114.6 (2)	C17—C18—H18	119.7
C23—N6—H6	122.7	C20—C19—C18	119.7 (4)
N5—N6—H6	122.7	C20—C19—H19	120.1
C23—N7—C22	108.6 (2)	C18—C19—H19	120.1
C23—N7—N8	129.7 (2)	C19—C20—C21	120.8 (4)
C22—N7—N8	121.5 (2)	C19—C20—H20	119.6
C24—N8—N7	116.3 (2)	C21—C20—H20	119.6
C6—C1—C2	121.3 (3)	C16—C21—C20	119.1 (3)
C6—C1—Cl1	118.1 (3)	C16—C21—H21	120.5
C2—C1—Cl1	120.6 (2)	C20—C21—H21	120.5
C3—C2—C1	117.3 (3)	N5—C22—N7	110.7 (3)
C3—C2—C7	120.6 (3)	N5—C22—C17	125.3 (3)
C1—C2—C7	122.1 (3)	N7—C22—C17	123.9 (3)
C4—C3—C2	121.3 (3)	N6—C23—N7	102.1 (2)
C4—C3—H3A	119.3	N6—C23—S2	127.3 (2)
C2—C3—H3A	119.3	N7—C23—S2	130.5 (2)
C5—C4—C3	119.6 (4)	N8—C24—C25	119.9 (3)
C5—C4—H4	120.2	N8—C24—H24	120.0
C3—C4—H4	120.2	C25—C24—H24	120.0
C6—C5—C4	120.6 (4)	C26—C25—C30	118.0 (3)
C6—C5—H5	119.7	C26—C25—C24	122.0 (3)
C4—C5—H5	119.7	C30—C25—C24	120.0 (3)
C5—C6—C1	119.8 (4)	C27—C26—C25	121.4 (3)
C5—C6—H6A	120.1	C27—C26—Cl4	118.0 (3)
C1—C6—H6A	120.1	C25—C26—Cl4	120.6 (2)
N1—C7—C2	118.5 (3)	C28—C27—C26	119.3 (4)
N1—C7—H7	120.8	C28—C27—H27	120.3
C2—C7—H7	120.8	C26—C27—H27	120.3
N3—C8—N2	116.5 (3)	C27—C28—C29	120.8 (4)
N3—C8—S1	119.8 (2)	C27—C28—H28	119.6
N2—C8—S1	123.7 (2)	C29—C28—H28	119.6
N4—C9—C10	122.2 (3)	C30—C29—C28	119.9 (4)
N4—C9—H9	118.9	C30—C29—H29	120.0
C10—C9—H9	118.9	C28—C29—H29	120.0
C15—C10—C11	116.9 (3)	C29—C30—C25	120.6 (4)
C15—C10—C9	121.4 (3)	C29—C30—H30	119.7
C11—C10—C9	121.7 (3)	C25—C30—H30	119.7
C12—C11—C10	121.6 (3)	C32—C31—H31A	109.5
C12—C11—Cl2	118.3 (3)	C32—C31—H31B	109.5
C10—C11—Cl2	120.1 (2)	H31A—C31—H31B	109.5
C13—C12—C11	119.8 (3)	C32—C31—H31C	109.5
C13—C12—H12	120.1	H31A—C31—H31C	109.5
C11—C12—H12	120.1	H31B—C31—H31C	109.5
C12—C13—C14	120.3 (4)	C31—C32—O1	122.3 (6)
C12—C13—H13	119.8	C31—C32—H32A	106.8
C14—C13—H13	119.8	O1—C32—H32A	106.8
C13—C14—C15	120.0 (4)	C31—C32—H32B	106.8
C13—C14—H14	120.0	O1—C32—H32B	106.8
C15—C14—H14	120.0	H32A—C32—H32B	106.6
C14—C15—C10	121.4 (3)

C7—N1—N2—C8	−173.4 (3)	C21—C16—C17—C22	−178.1 (3)
C8—N3—N4—C9	174.7 (3)	Cl3—C16—C17—C22	−1.6 (4)
C22—N5—N6—C23	−1.1 (4)	C16—C17—C18—C19	1.4 (5)
C23—N7—N8—C24	38.7 (4)	C22—C17—C18—C19	179.0 (3)
C22—N7—N8—C24	−147.1 (3)	C17—C18—C19—C20	−1.4 (5)
C6—C1—C2—C3	1.5 (5)	C18—C19—C20—C21	0.6 (6)
Cl1—C1—C2—C3	−176.9 (2)	C17—C16—C21—C20	−0.3 (5)
C6—C1—C2—C7	−180.0 (3)	Cl3—C16—C21—C20	−176.8 (3)
Cl1—C1—C2—C7	1.6 (4)	C19—C20—C21—C16	0.3 (6)
C1—C2—C3—C4	−0.2 (5)	N6—N5—C22—N7	2.1 (3)
C7—C2—C3—C4	−178.8 (3)	N6—N5—C22—C17	178.9 (3)
C2—C3—C4—C5	−1.1 (6)	C23—N7—C22—N5	−2.5 (4)
C3—C4—C5—C6	1.2 (6)	N8—N7—C22—N5	−177.7 (3)
C4—C5—C6—C1	0.1 (6)	C23—N7—C22—C17	−179.3 (3)
C2—C1—C6—C5	−1.5 (6)	N8—N7—C22—C17	5.5 (4)
Cl1—C1—C6—C5	176.9 (3)	C16—C17—C22—N5	115.1 (4)
N2—N1—C7—C2	178.9 (3)	C18—C17—C22—N5	−62.5 (4)
C3—C2—C7—N1	0.7 (5)	C16—C17—C22—N7	−68.6 (4)
C1—C2—C7—N1	−177.7 (3)	C18—C17—C22—N7	113.9 (3)
N4—N3—C8—N2	−2.2 (4)	N5—N6—C23—N7	−0.4 (3)
N4—N3—C8—S1	176.7 (2)	N5—N6—C23—S2	176.6 (2)
N1—N2—C8—N3	−178.5 (3)	C22—N7—C23—N6	1.6 (3)
N1—N2—C8—S1	2.6 (4)	N8—N7—C23—N6	176.4 (3)
N3—N4—C9—C10	178.8 (3)	C22—N7—C23—S2	−175.2 (3)
N4—C9—C10—C15	−1.7 (5)	N8—N7—C23—S2	−0.5 (5)
N4—C9—C10—C11	178.5 (3)	N7—N8—C24—C25	−177.3 (3)
C15—C10—C11—C12	−0.6 (5)	N8—C24—C25—C26	−173.1 (3)
C9—C10—C11—C12	179.3 (3)	N8—C24—C25—C30	7.1 (5)
C15—C10—C11—Cl2	−179.8 (2)	C30—C25—C26—C27	1.0 (5)
C9—C10—C11—Cl2	0.1 (4)	C24—C25—C26—C27	−178.8 (3)
C10—C11—C12—C13	1.0 (5)	C30—C25—C26—Cl4	−179.9 (3)
Cl2—C11—C12—C13	−179.8 (3)	C24—C25—C26—Cl4	0.3 (4)
C11—C12—C13—C14	−0.6 (6)	C25—C26—C27—C28	−0.2 (6)
C12—C13—C14—C15	−0.1 (6)	Cl4—C26—C27—C28	−179.3 (3)
C13—C14—C15—C10	0.6 (6)	C26—C27—C28—C29	−1.0 (7)
C11—C10—C15—C14	−0.2 (5)	C27—C28—C29—C30	1.3 (7)
C9—C10—C15—C14	179.9 (3)	C28—C29—C30—C25	−0.4 (6)
C21—C16—C17—C18	−0.5 (5)	C26—C25—C30—C29	−0.7 (5)
Cl3—C16—C17—C18	175.9 (2)	C24—C25—C30—C29	179.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.20	2.978 (4)	150
N6—H6···S1ⁱ	0.86	2.41	3.261 (3)	170
N3—H3···S2ⁱⁱ	0.86	2.56	3.410 (2)	169
O1—H1···S1ⁱⁱⁱ	0.82	2.65	3.413 (3)	156

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀Cl₂N₄S·C₁₅H₁₂Cl₂N₄S·C₂H₆O
M_r	746.54
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.7086 (6), 10.9999 (9), 20.9827 (16)
α, β, γ (°)	94.678 (1), 92.083 (1), 99.851 (1)
V (Å³)	1744.8 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.35 × 0.26 × 0.23

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.845, 0.894
No. of measured, independent and observed [I > 2σ(I)] reflections	9324, 6154, 3724
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.111, 1.01
No. of reflections	6154
No. of parameters	425
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.25

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1	0.86	2.20	2.978 (4)	150
N6—H6···S1ⁱ	0.86	2.41	3.261 (3)	170
N3—H3···S2ⁱⁱ	0.86	2.56	3.410 (2)	169
O1—H1···S1ⁱⁱⁱ	0.82	2.65	3.413 (3)	156

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

Acknowledgements

The author thanks the Postgraduate Foundation of Taishan University for financial support (grant No. Y06-2-10).

References

Bacci, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez-Arguelles, M. C., Rogolino, D., Solinas, C. & Zani, F. (2005). J. Inorg. Biochem. 99, 397–408. Web of Science PubMed Google Scholar
Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liang, F.-Z. (2003). J. Shandong Normal Univ. (Nat. Sci.), 18, 50–51. Google Scholar
Ren, Y. P., Dai, R. B., Wang, L. F. & Wu, J. G. (1999). Synth. Commun. 29, 613–617. CAS Google Scholar
Sen, A. K., Singh, R. N., Handa, R. N., Dubey, S. N. & Squattrito, P. J. (1998). J. Mol. Struct. 470, 61–69. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xia, H.-T., Liu, Y.-F., Yang, S.-P. & Wang, D.-Q. (2007). Acta Cryst. E63, o40–o41. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Yang, J. G. & Pan, F. Y. (2005). Chin. J. Struct. Chem. 24, 1403–1407. CAS Google Scholar

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

(E)-4-(2-Chloro­benzyl­­idene­amino)-3-(2-chloro­phen­yl)-1H-1,2,4-triazole-5(4H)-thione–(E)-1,5-bis­­(2-chloro­benzyl­­idene)thio­carbonohydrazide–methanol (1/1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-4-(2-Chlorobenzylideneamino)-3-(2-chlorophenyl)-1H-1,2,4-triazole-5(4H)-thione–(E)-1,5-bis(2-chlorobenzylidene)thiocarbonohydrazide–methanol (1/1/1)