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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o141.
Published online 2009 December 16. doi:  10.1107/S1600536809053203
PMCID: PMC2980177

(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)

Abstract

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 [triangle]); Yang et al. (2005 [triangle]); Sen et al. (1998 [triangle]); Xia et al. (2007 [triangle]). For the biological activity of Schiff bases, see: Liang (2003 [triangle]); Bacci et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o141-scheme1.jpg

Experimental

Crystal data

  • C15H10Cl2N4S·C15H12Cl2N4S·C2H6O
  • M r = 746.54
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o141-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.111
  • S = 1.01
  • 6154 reflections
  • 425 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

The H atoms were found in a difference map, then placed in idealized positions (C-H = 0.93–0.97 Å, N-H = 0.86 Å and O-H = 0.82 Å), and refined using a riding model, with Uiso(H) = 1.2Ueq(C,N) and 1.5Ueq(O,Cmethyl).

Figures

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.

Crystal data

C15H10Cl2N4S·C15H12Cl2N4S·C2H6OZ = 2
Mr = 746.54F(000) = 768
Triclinic, P1Dx = 1.421 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.7086 (6) ÅCell parameters from 1667 reflections
b = 10.9999 (9) Åθ = 2.2–20.5°
c = 20.9827 (16) ŵ = 0.50 mm1
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

Bruker SMART APEX diffractometer6154 independent reflections
Radiation source: fine-focus sealed tube3724 reflections with I > 2σ(I)
graphiteRint = 0.026
[var phi] and ω scansθmax = 25.1°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→9
Tmin = 0.845, Tmax = 0.894k = −12→13
9324 measured reflectionsl = −24→24

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0365P)2 + 0.4564P] where P = (Fo2 + 2Fc2)/3
6154 reflections(Δ/σ)max = 0.001
425 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.25 e Å3

Special details

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)

xyzUiso*/Ueq
S10.25610 (13)1.26698 (8)0.43362 (4)0.0574 (3)
S20.40630 (12)0.14705 (9)0.24096 (4)0.0614 (3)
Cl10.15231 (15)0.94451 (10)0.71997 (4)0.0836 (3)
Cl20.48468 (13)0.77336 (9)0.21104 (4)0.0738 (3)
Cl30.21316 (12)0.52305 (8)0.10925 (5)0.0689 (3)
Cl40.22413 (15)−0.15631 (9)0.07317 (5)0.0861 (3)
O10.1682 (4)0.7954 (3)0.52080 (14)0.0837 (8)
H10.06080.79010.52110.126*
N10.1820 (3)1.1229 (2)0.54344 (12)0.0487 (7)
N20.2441 (3)1.0597 (2)0.49247 (11)0.0472 (7)
H20.26080.98470.49440.057*
N30.3341 (3)1.0539 (2)0.39024 (11)0.0506 (7)
H30.35341.08770.35500.061*
N40.3618 (3)0.9349 (2)0.39441 (11)0.0468 (6)
N50.0553 (4)0.3611 (2)0.26242 (12)0.0529 (7)
N60.1796 (3)0.2949 (2)0.28209 (11)0.0542 (7)
H60.21210.29430.32170.065*
N70.1565 (3)0.2589 (2)0.18135 (11)0.0459 (6)
N80.1743 (3)0.2251 (2)0.11665 (11)0.0463 (6)
C10.0902 (4)1.0862 (3)0.70951 (15)0.0566 (9)
C20.1044 (4)1.1357 (3)0.65067 (14)0.0463 (8)
C30.0605 (4)1.2523 (3)0.64682 (16)0.0607 (9)
H3A0.06901.28800.60810.073*
C40.0045 (5)1.3162 (4)0.6992 (2)0.0762 (11)
H4−0.02241.39480.69600.091*
C5−0.0114 (5)1.2632 (5)0.7562 (2)0.0841 (13)
H5−0.05121.30570.79130.101*
C60.0306 (5)1.1495 (4)0.76173 (17)0.0767 (12)
H6A0.01921.11410.80050.092*
C70.1671 (4)1.0702 (3)0.59493 (14)0.0480 (8)
H70.19530.99180.59730.058*
C80.2777 (4)1.1187 (3)0.43966 (14)0.0434 (7)
C90.4020 (4)0.8808 (3)0.34211 (15)0.0499 (8)
H90.40750.92310.30540.060*
C100.4389 (4)0.7564 (3)0.33816 (14)0.0455 (8)
C110.4785 (4)0.6972 (3)0.28059 (15)0.0515 (8)
C120.5155 (5)0.5792 (3)0.27706 (19)0.0674 (10)
H120.54340.54200.23830.081*
C130.5112 (5)0.5166 (4)0.3307 (2)0.0785 (12)
H130.53510.43640.32830.094*
C140.4719 (5)0.5714 (3)0.3881 (2)0.0758 (11)
H140.46880.52840.42450.091*
C150.4369 (4)0.6898 (3)0.39182 (16)0.0596 (9)
H150.41140.72650.43110.072*
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)
H18−0.29670.30190.19070.072*
C19−0.3681 (5)0.4010 (4)0.12104 (19)0.0719 (11)
H19−0.48910.37650.12350.086*
C20−0.3039 (6)0.4819 (4)0.07809 (18)0.0759 (12)
H20−0.38190.51300.05160.091*
C21−0.1245 (5)0.5180 (3)0.07351 (16)0.0667 (10)
H21−0.08140.57350.04430.080*
C220.0461 (4)0.3399 (3)0.20069 (14)0.0443 (8)
C230.2465 (4)0.2311 (3)0.23466 (14)0.0460 (8)
C240.2022 (4)0.1161 (3)0.10273 (14)0.0486 (8)
H240.20490.06240.13460.058*
C250.2301 (4)0.0749 (3)0.03672 (14)0.0479 (8)
C260.2425 (4)−0.0464 (3)0.01809 (15)0.0561 (9)
C270.2720 (5)−0.0836 (4)−0.0444 (2)0.0790 (12)
H270.2803−0.1657−0.05610.095*
C280.2890 (6)0.0012 (5)−0.08861 (19)0.0903 (14)
H280.3108−0.0233−0.13060.108*
C290.2744 (6)0.1223 (5)−0.07193 (18)0.0872 (13)
H290.28390.1789−0.10270.105*
C300.2458 (5)0.1594 (3)−0.00994 (15)0.0651 (10)
H300.23660.24150.00130.078*
C310.1607 (8)0.5962 (6)0.5595 (4)0.192 (4)
H31A0.03410.58220.55740.288*
H31B0.20230.56180.59660.288*
H31C0.20140.55720.52170.288*
C320.2229 (7)0.7192 (6)0.5636 (3)0.137 (2)
H32A0.35010.72900.56210.164*
H32B0.19860.75240.60600.164*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0842 (7)0.0466 (5)0.0462 (5)0.0223 (5)0.0086 (4)0.0072 (4)
S20.0711 (6)0.0711 (6)0.0526 (5)0.0330 (5)0.0123 (5)0.0211 (5)
Cl10.1144 (9)0.0774 (7)0.0609 (6)0.0123 (6)0.0128 (6)0.0226 (5)
Cl20.0862 (7)0.0867 (7)0.0473 (5)0.0142 (6)0.0118 (5)−0.0027 (5)
Cl30.0576 (6)0.0654 (6)0.0864 (7)0.0088 (5)0.0044 (5)0.0266 (5)
Cl40.1162 (9)0.0531 (6)0.0935 (8)0.0272 (6)0.0055 (6)0.0064 (5)
O10.086 (2)0.0733 (18)0.099 (2)0.0229 (17)0.0189 (17)0.0211 (16)
N10.0572 (18)0.0483 (16)0.0421 (15)0.0134 (13)0.0085 (13)0.0011 (13)
N20.0617 (18)0.0441 (15)0.0402 (14)0.0176 (13)0.0103 (13)0.0080 (12)
N30.0725 (19)0.0443 (16)0.0391 (14)0.0180 (14)0.0112 (13)0.0080 (12)
N40.0585 (18)0.0404 (15)0.0442 (15)0.0139 (13)0.0096 (13)0.0052 (12)
N50.071 (2)0.0499 (17)0.0428 (15)0.0239 (15)0.0053 (14)0.0018 (13)
N60.073 (2)0.0553 (17)0.0381 (15)0.0198 (15)0.0002 (14)0.0066 (13)
N70.0568 (17)0.0475 (16)0.0378 (14)0.0186 (13)0.0076 (13)0.0071 (12)
N80.0552 (17)0.0499 (17)0.0374 (14)0.0180 (13)0.0080 (12)0.0049 (12)
C10.049 (2)0.070 (2)0.0462 (19)0.0005 (18)0.0070 (16)−0.0004 (18)
C20.0424 (19)0.050 (2)0.0436 (18)0.0020 (16)0.0050 (15)−0.0025 (16)
C30.059 (2)0.066 (2)0.056 (2)0.0138 (19)0.0020 (18)−0.0050 (19)
C40.069 (3)0.074 (3)0.084 (3)0.021 (2)0.003 (2)−0.021 (2)
C50.072 (3)0.108 (4)0.068 (3)0.016 (3)0.019 (2)−0.027 (3)
C60.077 (3)0.101 (3)0.046 (2)0.002 (3)0.016 (2)−0.005 (2)
C70.052 (2)0.0485 (19)0.0436 (18)0.0088 (16)0.0053 (15)0.0021 (16)
C80.0454 (19)0.0458 (19)0.0402 (17)0.0115 (15)0.0025 (14)0.0045 (15)
C90.059 (2)0.047 (2)0.0444 (18)0.0098 (17)0.0050 (16)0.0072 (16)
C100.047 (2)0.0381 (18)0.0503 (19)0.0071 (15)0.0035 (15)−0.0002 (15)
C110.045 (2)0.053 (2)0.055 (2)0.0086 (16)−0.0013 (16)−0.0042 (17)
C120.065 (3)0.058 (2)0.077 (3)0.016 (2)0.001 (2)−0.017 (2)
C130.081 (3)0.048 (2)0.107 (3)0.021 (2)−0.008 (3)−0.004 (2)
C140.092 (3)0.054 (2)0.083 (3)0.019 (2)−0.007 (2)0.013 (2)
C150.070 (3)0.049 (2)0.061 (2)0.0120 (18)0.0052 (19)0.0037 (18)
C160.050 (2)0.050 (2)0.0506 (19)0.0145 (16)−0.0002 (16)−0.0009 (16)
C170.055 (2)0.0372 (17)0.0430 (17)0.0168 (16)0.0058 (15)−0.0046 (14)
C180.060 (2)0.059 (2)0.063 (2)0.0171 (19)0.0163 (19)−0.0038 (18)
C190.052 (2)0.081 (3)0.084 (3)0.023 (2)0.003 (2)−0.007 (2)
C200.071 (3)0.096 (3)0.069 (3)0.042 (3)−0.009 (2)0.003 (2)
C210.072 (3)0.078 (3)0.058 (2)0.031 (2)0.002 (2)0.018 (2)
C220.052 (2)0.0393 (18)0.0441 (18)0.0124 (15)0.0102 (15)0.0049 (15)
C230.057 (2)0.0432 (18)0.0390 (17)0.0106 (16)0.0048 (15)0.0058 (15)
C240.060 (2)0.047 (2)0.0419 (18)0.0171 (17)0.0053 (16)0.0078 (15)
C250.049 (2)0.055 (2)0.0431 (18)0.0173 (16)0.0067 (15)0.0044 (16)
C260.056 (2)0.059 (2)0.054 (2)0.0198 (18)−0.0012 (17)−0.0064 (18)
C270.081 (3)0.083 (3)0.073 (3)0.030 (2)0.003 (2)−0.025 (2)
C280.092 (3)0.130 (4)0.048 (2)0.031 (3)0.006 (2)−0.023 (3)
C290.106 (4)0.114 (4)0.048 (2)0.030 (3)0.021 (2)0.015 (2)
C300.078 (3)0.073 (3)0.051 (2)0.027 (2)0.0156 (19)0.0117 (19)
C310.122 (5)0.109 (5)0.359 (11)0.040 (4)−0.016 (6)0.079 (6)
C320.084 (4)0.125 (5)0.211 (7)0.027 (4)−0.004 (4)0.056 (5)

Geometric parameters (Å, °)

S1—C81.682 (3)C10—C111.394 (4)
S2—C231.669 (3)C11—C121.373 (4)
Cl1—C11.735 (4)C12—C131.364 (5)
Cl2—C111.739 (3)C12—H120.93
Cl3—C161.730 (3)C13—C141.370 (5)
Cl4—C261.732 (3)C13—H130.93
O1—C321.380 (5)C14—C151.371 (4)
O1—H10.82C14—H140.93
N1—C71.267 (3)C15—H150.93
N1—N21.373 (3)C16—C211.371 (4)
N2—C81.341 (3)C16—C171.383 (4)
N2—H20.86C17—C181.383 (4)
N3—C81.338 (3)C17—C221.474 (4)
N3—N41.372 (3)C18—C191.378 (5)
N3—H30.86C18—H180.93
N4—C91.279 (3)C19—C201.365 (5)
N5—C221.294 (3)C19—H190.93
N5—N61.370 (3)C20—C211.381 (5)
N6—C231.340 (3)C20—H200.93
N6—H60.86C21—H210.93
N7—C231.378 (3)C24—C251.457 (4)
N7—C221.382 (3)C24—H240.93
N7—N81.396 (3)C25—C261.380 (4)
N8—C241.267 (3)C25—C301.398 (4)
C1—C61.385 (4)C26—C271.379 (5)
C1—C21.389 (4)C27—C281.363 (5)
C2—C31.390 (4)C27—H270.93
C2—C71.463 (4)C28—C291.374 (6)
C3—C41.379 (4)C28—H280.93
C3—H3A0.93C29—C301.368 (5)
C4—C51.372 (5)C29—H290.93
C4—H40.93C30—H300.93
C5—C61.358 (5)C31—C321.350 (7)
C5—H50.93C31—H31A0.96
C6—H6A0.93C31—H31B0.96
C7—H70.93C31—H31C0.96
C9—C101.441 (4)C32—H32A0.97
C9—H90.93C32—H32B0.97
C10—C151.391 (4)
C32—O1—H1109.5C14—C15—H15119.3
C7—N1—N2116.9 (2)C10—C15—H15119.3
C8—N2—N1117.8 (2)C21—C16—C17121.3 (3)
C8—N2—H2121.1C21—C16—Cl3118.6 (3)
N1—N2—H2121.1C17—C16—Cl3120.0 (2)
C8—N3—N4121.6 (2)C16—C17—C18118.5 (3)
C8—N3—H3119.2C16—C17—C22122.6 (3)
N4—N3—H3119.2C18—C17—C22118.9 (3)
C9—N4—N3114.8 (2)C19—C18—C17120.7 (3)
C22—N5—N6103.9 (2)C19—C18—H18119.7
C23—N6—N5114.6 (2)C17—C18—H18119.7
C23—N6—H6122.7C20—C19—C18119.7 (4)
N5—N6—H6122.7C20—C19—H19120.1
C23—N7—C22108.6 (2)C18—C19—H19120.1
C23—N7—N8129.7 (2)C19—C20—C21120.8 (4)
C22—N7—N8121.5 (2)C19—C20—H20119.6
C24—N8—N7116.3 (2)C21—C20—H20119.6
C6—C1—C2121.3 (3)C16—C21—C20119.1 (3)
C6—C1—Cl1118.1 (3)C16—C21—H21120.5
C2—C1—Cl1120.6 (2)C20—C21—H21120.5
C3—C2—C1117.3 (3)N5—C22—N7110.7 (3)
C3—C2—C7120.6 (3)N5—C22—C17125.3 (3)
C1—C2—C7122.1 (3)N7—C22—C17123.9 (3)
C4—C3—C2121.3 (3)N6—C23—N7102.1 (2)
C4—C3—H3A119.3N6—C23—S2127.3 (2)
C2—C3—H3A119.3N7—C23—S2130.5 (2)
C5—C4—C3119.6 (4)N8—C24—C25119.9 (3)
C5—C4—H4120.2N8—C24—H24120.0
C3—C4—H4120.2C25—C24—H24120.0
C6—C5—C4120.6 (4)C26—C25—C30118.0 (3)
C6—C5—H5119.7C26—C25—C24122.0 (3)
C4—C5—H5119.7C30—C25—C24120.0 (3)
C5—C6—C1119.8 (4)C27—C26—C25121.4 (3)
C5—C6—H6A120.1C27—C26—Cl4118.0 (3)
C1—C6—H6A120.1C25—C26—Cl4120.6 (2)
N1—C7—C2118.5 (3)C28—C27—C26119.3 (4)
N1—C7—H7120.8C28—C27—H27120.3
C2—C7—H7120.8C26—C27—H27120.3
N3—C8—N2116.5 (3)C27—C28—C29120.8 (4)
N3—C8—S1119.8 (2)C27—C28—H28119.6
N2—C8—S1123.7 (2)C29—C28—H28119.6
N4—C9—C10122.2 (3)C30—C29—C28119.9 (4)
N4—C9—H9118.9C30—C29—H29120.0
C10—C9—H9118.9C28—C29—H29120.0
C15—C10—C11116.9 (3)C29—C30—C25120.6 (4)
C15—C10—C9121.4 (3)C29—C30—H30119.7
C11—C10—C9121.7 (3)C25—C30—H30119.7
C12—C11—C10121.6 (3)C32—C31—H31A109.5
C12—C11—Cl2118.3 (3)C32—C31—H31B109.5
C10—C11—Cl2120.1 (2)H31A—C31—H31B109.5
C13—C12—C11119.8 (3)C32—C31—H31C109.5
C13—C12—H12120.1H31A—C31—H31C109.5
C11—C12—H12120.1H31B—C31—H31C109.5
C12—C13—C14120.3 (4)C31—C32—O1122.3 (6)
C12—C13—H13119.8C31—C32—H32A106.8
C14—C13—H13119.8O1—C32—H32A106.8
C13—C14—C15120.0 (4)C31—C32—H32B106.8
C13—C14—H14120.0O1—C32—H32B106.8
C15—C14—H14120.0H32A—C32—H32B106.6
C14—C15—C10121.4 (3)
C7—N1—N2—C8−173.4 (3)C21—C16—C17—C22−178.1 (3)
C8—N3—N4—C9174.7 (3)Cl3—C16—C17—C22−1.6 (4)
C22—N5—N6—C23−1.1 (4)C16—C17—C18—C191.4 (5)
C23—N7—N8—C2438.7 (4)C22—C17—C18—C19179.0 (3)
C22—N7—N8—C24−147.1 (3)C17—C18—C19—C20−1.4 (5)
C6—C1—C2—C31.5 (5)C18—C19—C20—C210.6 (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—C71.6 (4)C19—C20—C21—C160.3 (6)
C1—C2—C3—C4−0.2 (5)N6—N5—C22—N72.1 (3)
C7—C2—C3—C4−178.8 (3)N6—N5—C22—C17178.9 (3)
C2—C3—C4—C5−1.1 (6)C23—N7—C22—N5−2.5 (4)
C3—C4—C5—C61.2 (6)N8—N7—C22—N5−177.7 (3)
C4—C5—C6—C10.1 (6)C23—N7—C22—C17−179.3 (3)
C2—C1—C6—C5−1.5 (6)N8—N7—C22—C175.5 (4)
Cl1—C1—C6—C5176.9 (3)C16—C17—C22—N5115.1 (4)
N2—N1—C7—C2178.9 (3)C18—C17—C22—N5−62.5 (4)
C3—C2—C7—N10.7 (5)C16—C17—C22—N7−68.6 (4)
C1—C2—C7—N1−177.7 (3)C18—C17—C22—N7113.9 (3)
N4—N3—C8—N2−2.2 (4)N5—N6—C23—N7−0.4 (3)
N4—N3—C8—S1176.7 (2)N5—N6—C23—S2176.6 (2)
N1—N2—C8—N3−178.5 (3)C22—N7—C23—N61.6 (3)
N1—N2—C8—S12.6 (4)N8—N7—C23—N6176.4 (3)
N3—N4—C9—C10178.8 (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—C11178.5 (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—C12179.3 (3)N8—C24—C25—C307.1 (5)
C15—C10—C11—Cl2−179.8 (2)C30—C25—C26—C271.0 (5)
C9—C10—C11—Cl20.1 (4)C24—C25—C26—C27−178.8 (3)
C10—C11—C12—C131.0 (5)C30—C25—C26—Cl4−179.9 (3)
Cl2—C11—C12—C13−179.8 (3)C24—C25—C26—Cl40.3 (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—C100.6 (6)C26—C27—C28—C29−1.0 (7)
C11—C10—C15—C14−0.2 (5)C27—C28—C29—C301.3 (7)
C9—C10—C15—C14179.9 (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—C18175.9 (2)C24—C25—C30—C29179.1 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O10.862.202.978 (4)150
N6—H6···S1i0.862.413.261 (3)170
N3—H3···S2ii0.862.563.410 (2)169
O1—H1···S1iii0.822.653.413 (3)156

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2984).

References

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