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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Nov 8;64(Pt 12):o2249. doi: 10.1107/S1600536808034892

Benzyl N′-(2-chloro­benzyl­idene)hydrazinecarbodithio­ate

Zhi-Qiang Shi a,*, Ning-Ning Ji b, Qin-Qin Ji c
PMCID: PMC2960048  PMID: 21581230

Abstract

The asymmetric unit of the title compound, C15H13ClN2S2, contains two independent mol­ecules, which are linked into a pseudo-centrosymmetric dimer by inter­molecular N—H⋯S hydrogen bonds. The aromatic rings form dihedral angles of 67.06 (3) and 81.85 (2)° in the two independent mol­ecules.

Related literature

For the biomedical properties of ligands derived from S-benzyl­dithio­carbaza­te, see: Ali et al. (2001 ▶, 2002 ▶); Tarafder et al. (2001 ▶, 2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).graphic file with name e-64-o2249-scheme1.jpg

Experimental

Crystal data

  • C15H13ClN2S2

  • M r = 320.84

  • Triclinic, Inline graphic

  • a = 11.877 (2) Å

  • b = 11.906 (2) Å

  • c = 12.623 (3) Å

  • α = 68.242 (3)°

  • β = 71.116 (4)°

  • γ = 82.335 (4)°

  • V = 1568.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.50 mm−1

  • T = 295 (2) K

  • 0.12 × 0.10 × 0.06 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.942, T max = 0.971

  • 8397 measured reflections

  • 5524 independent reflections

  • 3436 reflections with I > 2σ(I)

  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046

  • wR(F 2) = 0.127

  • S = 0.97

  • 5524 reflections

  • 361 parameters

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2 and SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL .

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034892/cv2453sup1.cif

e-64-o2249-sup1.cif (24.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034892/cv2453Isup2.hkl

e-64-o2249-Isup2.hkl (270.4KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯S4 0.86 2.56 3.405 (3) 166
N3—H3A⋯S2 0.86 2.60 3.451 (3) 169
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Acknowledgments

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06–2–08).

supplementary crystallographic information

Comment

In recent years, the intriguing coordination chemistry and increasingly important biomedical properties of ligands derived from S-benzyldithiocarbazate(SBDTC) have received much attention (Ali et al., 2001, 2002; Tarafder et al., 2001, 2008). In order to search for new ligands derived from SBDTC, the title compound, (I), was synthesized. Herewith we present its crystal structure.

In (I), all bond lengths and angles are normal (Allen et al., 1987). The C=N bond length in the independent molecules are 1.279 (3) Å(C7=N2) and 1.271 (4) Å(C22=N4), respectively, showing the double-bond character. The C=S bond lengths of 1.656 (3) Å(S2=C8) and 1.661 (3) Å(S4=C23) are intermediate between the values of 1.82Å for a C—S single bond and 1.56Å for a C=S double bond. The C=N—N angles in the independent molecule of 115.5 (2)° and 115.6 (3)° are significantly smaller than the ideal value of 120° expected for sp2-hybridized N atoms. This is probably a consequence of repulsion between the nitrogen lone pairs and the adjacent N bonds.

Two independent molecules are linked by N—H···S hydrogen bonds (Table 1) into pseudo-centrosymmetric dimers (Fig. 1).

Experimental

The title compound was synthesized by the reaction of hydrazinecarbodithioic acid benzyl ester(1 mmol, 198.3 mg) with 2-chloro-benzaldehyde(1 mmol, 140.6 mg) in ethanol(20 ml) under reflux conditions (343 K) for 6 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After five days yellow crystals suitable for X-ray diffraction study were obtained.

Refinement

All H atoms were placed in idealized positions (C—H = 0.93— 0.97 Å, N—H = 0.86 Å) and refined as riding atoms. For those bound to C, Uiso(H) = 1.2 or 1.5Ueq(C). while for those bound to N, Uiso(H) = 1.2 Ueq(N).

Figures

Fig. 1.

Fig. 1.

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The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. Dashed lines indicate hydrogen bonds.

Crystal data

C15H13ClN2S2 Z = 4
Mr = 320.84 F000 = 664
Triclinic, P1 Dx = 1.359 Mg m−3
Hall symbol: -P 1 Mo Kα radiation λ = 0.71073 Å
a = 11.877 (2) Å Cell parameters from 1618 reflections
b = 11.906 (2) Å θ = 2.6–24.6º
c = 12.623 (3) Å µ = 0.50 mm−1
α = 68.242 (3)º T = 295 (2) K
β = 71.116 (4)º Block, yellow
γ = 82.335 (4)º 0.12 × 0.10 × 0.06 mm
V = 1568.4 (5) Å3
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Data collection

Bruker APEXII CCD area-detector diffractometer 5524 independent reflections
Radiation source: fine-focus sealed tube 3436 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.026
T = 295(2) K θmax = 25.1º
φ and ω scans θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005) h = −11→14
Tmin = 0.942, Tmax = 0.971 k = −14→13
8397 measured reflections l = −14→14
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Refinement

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)] = 0.046 H-atom parameters constrained
wR(F2) = 0.127   w = 1/[σ2(Fo2) + (0.0533P)2 + 0.4623P] where P = (Fo2 + 2Fc2)/3
S = 0.97 (Δ/σ)max = 0.001
5524 reflections Δρmax = 0.44 e Å−3
361 parameters Δρmin = −0.46 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Cl2 0.61916 (10) 0.15814 (11) 0.57081 (9) 0.0994 (4)
S3 0.36389 (7) 0.66976 (8) 0.21058 (7) 0.0541 (3)
S4 0.15028 (7) 0.61729 (8) 0.43141 (7) 0.0566 (3)
N3 0.3563 (2) 0.5043 (2) 0.4167 (2) 0.0514 (7)
H3A 0.3270 0.4634 0.4914 0.062*
N4 0.4704 (2) 0.4789 (2) 0.3570 (2) 0.0478 (7)
C16 0.6959 (3) 0.2483 (3) 0.4266 (3) 0.0544 (9)
C17 0.6419 (3) 0.3506 (3) 0.3648 (3) 0.0455 (8)
C18 0.7096 (3) 0.4188 (3) 0.2498 (3) 0.0554 (9)
H18 0.6770 0.4888 0.2056 0.066*
C19 0.8242 (3) 0.3835 (3) 0.2014 (3) 0.0606 (10)
H19 0.8678 0.4290 0.1244 0.073*
C20 0.8742 (3) 0.2812 (4) 0.2663 (3) 0.0617 (10)
H20 0.9518 0.2584 0.2332 0.074*
C21 0.8112 (3) 0.2133 (3) 0.3785 (3) 0.0631 (10)
H21 0.8452 0.1443 0.4224 0.076*
C22 0.5211 (3) 0.3882 (3) 0.4168 (3) 0.0504 (8)
H22 0.4802 0.3449 0.4955 0.061*
C23 0.2902 (3) 0.5914 (3) 0.3608 (3) 0.0441 (8)
C24 0.2502 (3) 0.7786 (3) 0.1668 (3) 0.0612 (10)
H24A 0.1772 0.7372 0.1861 0.073*
H24B 0.2335 0.8347 0.2097 0.073*
C25 0.2944 (3) 0.8461 (3) 0.0345 (3) 0.0480 (8)
C26 0.3717 (3) 0.9404 (3) −0.0123 (3) 0.0609 (10)
H26 0.3981 0.9628 0.0389 0.073*
C27 0.4111 (3) 1.0026 (3) −0.1335 (3) 0.0689 (11)
H27 0.4636 1.0661 −0.1634 0.083*
C28 0.3730 (3) 0.9712 (4) −0.2098 (3) 0.0684 (11)
H28 0.3994 1.0132 −0.2916 0.082*
C29 0.2967 (3) 0.8785 (4) −0.1655 (3) 0.0716 (11)
H29 0.2702 0.8573 −0.2172 0.086*
C30 0.2579 (3) 0.8152 (3) −0.0442 (3) 0.0623 (10)
H30 0.2065 0.7509 −0.0151 0.075*
Cl1 −0.22425 (9) 0.74778 (9) 0.55632 (8) 0.0702 (3)
S1 0.06032 (8) 0.28590 (8) 0.93397 (7) 0.0589 (3)
S2 0.25595 (8) 0.30266 (9) 0.70505 (7) 0.0619 (3)
N1 0.0603 (2) 0.4336 (2) 0.7232 (2) 0.0497 (7)
H1 0.0857 0.4679 0.6469 0.060*
N2 −0.0472 (2) 0.4698 (2) 0.7859 (2) 0.0466 (7)
C1 −0.2804 (3) 0.6881 (3) 0.7111 (3) 0.0492 (8)
C2 −0.2159 (3) 0.6018 (3) 0.7786 (3) 0.0444 (8)
C3 −0.2674 (3) 0.5582 (3) 0.9025 (3) 0.0577 (9)
H3 −0.2269 0.5002 0.9504 0.069*
C4 −0.3772 (3) 0.5999 (4) 0.9548 (3) 0.0728 (11)
H4 −0.4098 0.5708 1.0375 0.087*
C5 −0.4383 (3) 0.6844 (4) 0.8849 (4) 0.0804 (13)
H5 −0.5128 0.7118 0.9205 0.097*
C6 −0.3909 (3) 0.7286 (4) 0.7634 (3) 0.0669 (10)
H6 −0.4329 0.7857 0.7164 0.080*
C7 −0.1006 (3) 0.5565 (3) 0.7233 (3) 0.0461 (8)
H7 −0.0652 0.5910 0.6413 0.055*
C8 0.1257 (3) 0.3461 (3) 0.7791 (3) 0.0446 (8)
C9 0.1668 (3) 0.1677 (3) 0.9769 (3) 0.0613 (10)
H9A 0.1802 0.1150 0.9308 0.074*
H9B 0.2421 0.2030 0.9614 0.074*
C10 0.1176 (3) 0.0961 (3) 1.1086 (3) 0.0476 (8)
C11 0.1692 (3) 0.1043 (3) 1.1888 (3) 0.0572 (9)
H11 0.2325 0.1561 1.1620 0.069*
C12 0.1273 (3) 0.0359 (3) 1.3090 (3) 0.0639 (10)
H12 0.1632 0.0415 1.3622 0.077*
C13 0.0338 (3) −0.0398 (3) 1.3501 (3) 0.0632 (10)
H13 0.0060 −0.0854 1.4310 0.076*
C14 −0.0190 (3) −0.0484 (3) 1.2711 (3) 0.0672 (11)
H14 −0.0827 −0.0999 1.2983 0.081*
C15 0.0231 (3) 0.0200 (3) 1.1512 (3) 0.0617 (10)
H15 −0.0132 0.0144 1.0982 0.074*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Cl2 0.0801 (8) 0.0990 (9) 0.0654 (7) 0.0195 (6) −0.0101 (6) 0.0142 (6)
S3 0.0454 (5) 0.0542 (6) 0.0410 (5) 0.0071 (4) −0.0009 (4) −0.0054 (4)
S4 0.0451 (5) 0.0626 (6) 0.0416 (5) 0.0100 (4) −0.0017 (4) −0.0085 (4)
N3 0.0410 (16) 0.0570 (18) 0.0386 (15) 0.0077 (13) −0.0044 (12) −0.0063 (13)
N4 0.0396 (15) 0.0508 (17) 0.0441 (16) 0.0053 (13) −0.0071 (13) −0.0135 (13)
C16 0.046 (2) 0.064 (2) 0.0444 (19) 0.0060 (17) −0.0116 (16) −0.0131 (17)
C17 0.0387 (18) 0.050 (2) 0.0456 (18) 0.0053 (15) −0.0141 (15) −0.0155 (16)
C18 0.051 (2) 0.056 (2) 0.054 (2) 0.0006 (17) −0.0130 (17) −0.0162 (17)
C19 0.056 (2) 0.069 (3) 0.052 (2) −0.005 (2) −0.0029 (18) −0.0267 (19)
C20 0.045 (2) 0.077 (3) 0.070 (3) 0.012 (2) −0.0156 (19) −0.040 (2)
C21 0.057 (2) 0.071 (3) 0.063 (2) 0.019 (2) −0.027 (2) −0.025 (2)
C22 0.047 (2) 0.052 (2) 0.0402 (18) 0.0013 (17) −0.0081 (16) −0.0086 (16)
C23 0.0441 (18) 0.0427 (19) 0.0399 (17) 0.0017 (15) −0.0081 (15) −0.0126 (15)
C24 0.049 (2) 0.059 (2) 0.051 (2) 0.0140 (17) −0.0038 (17) −0.0065 (17)
C25 0.0372 (18) 0.045 (2) 0.0478 (19) 0.0061 (15) −0.0070 (15) −0.0073 (16)
C26 0.064 (2) 0.065 (2) 0.051 (2) −0.010 (2) −0.0216 (18) −0.0108 (19)
C27 0.073 (3) 0.062 (3) 0.057 (2) −0.020 (2) −0.014 (2) −0.002 (2)
C28 0.064 (2) 0.075 (3) 0.048 (2) 0.002 (2) −0.0136 (19) −0.004 (2)
C29 0.064 (2) 0.093 (3) 0.060 (2) 0.000 (2) −0.026 (2) −0.024 (2)
C30 0.044 (2) 0.060 (2) 0.077 (3) −0.0071 (18) −0.0144 (19) −0.019 (2)
Cl1 0.0795 (7) 0.0724 (7) 0.0449 (5) 0.0055 (5) −0.0195 (5) −0.0065 (4)
S1 0.0544 (5) 0.0630 (6) 0.0368 (5) 0.0098 (4) −0.0037 (4) −0.0044 (4)
S2 0.0575 (6) 0.0645 (6) 0.0414 (5) 0.0168 (5) −0.0038 (4) −0.0092 (4)
N1 0.0471 (16) 0.0566 (18) 0.0324 (14) 0.0087 (14) −0.0064 (12) −0.0090 (13)
N2 0.0382 (15) 0.0541 (17) 0.0400 (15) 0.0016 (13) −0.0064 (12) −0.0133 (13)
C1 0.050 (2) 0.053 (2) 0.0430 (19) 0.0028 (17) −0.0150 (16) −0.0158 (16)
C2 0.0414 (18) 0.048 (2) 0.0406 (18) −0.0013 (15) −0.0083 (15) −0.0144 (15)
C3 0.056 (2) 0.061 (2) 0.045 (2) 0.0045 (18) −0.0118 (17) −0.0111 (17)
C4 0.058 (2) 0.092 (3) 0.049 (2) 0.005 (2) −0.0011 (19) −0.019 (2)
C5 0.050 (2) 0.108 (4) 0.075 (3) 0.021 (2) −0.010 (2) −0.038 (3)
C6 0.057 (2) 0.078 (3) 0.065 (3) 0.019 (2) −0.025 (2) −0.025 (2)
C7 0.0427 (18) 0.050 (2) 0.0369 (17) 0.0004 (16) −0.0086 (15) −0.0086 (15)
C8 0.0452 (18) 0.0440 (19) 0.0380 (17) 0.0020 (15) −0.0105 (15) −0.0095 (15)
C9 0.059 (2) 0.061 (2) 0.044 (2) 0.0099 (18) −0.0101 (17) −0.0044 (17)
C10 0.053 (2) 0.044 (2) 0.0389 (17) 0.0089 (16) −0.0134 (16) −0.0101 (15)
C11 0.065 (2) 0.049 (2) 0.053 (2) −0.0041 (18) −0.0205 (18) −0.0095 (17)
C12 0.076 (3) 0.070 (3) 0.047 (2) 0.009 (2) −0.026 (2) −0.0189 (19)
C13 0.077 (3) 0.060 (2) 0.0364 (19) 0.010 (2) −0.0092 (19) −0.0085 (17)
C14 0.066 (2) 0.065 (3) 0.055 (2) −0.011 (2) −0.007 (2) −0.011 (2)
C15 0.066 (2) 0.069 (3) 0.050 (2) −0.003 (2) −0.0174 (19) −0.0199 (19)
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Geometric parameters (Å, °)

Cl2—C16 1.742 (3) Cl1—C1 1.738 (3)
S3—C23 1.750 (3) S1—C8 1.751 (3)
S3—C24 1.815 (3) S1—C9 1.810 (3)
S4—C23 1.662 (3) S2—C8 1.657 (3)
N3—C23 1.337 (4) N1—C8 1.334 (4)
N3—N4 1.376 (3) N1—N2 1.375 (3)
N3—H3A 0.8600 N1—H1 0.8600
N4—C22 1.271 (4) N2—C7 1.279 (4)
C16—C17 1.384 (4) C1—C6 1.377 (5)
C16—C21 1.384 (5) C1—C2 1.390 (4)
C17—C18 1.399 (4) C2—C3 1.398 (4)
C17—C22 1.458 (4) C2—C7 1.455 (4)
C18—C19 1.380 (5) C3—C4 1.376 (5)
C18—H18 0.9300 C3—H3 0.9300
C19—C20 1.375 (5) C4—C5 1.371 (5)
C19—H19 0.9300 C4—H4 0.9300
C20—C21 1.358 (5) C5—C6 1.366 (5)
C20—H20 0.9300 C5—H5 0.9300
C21—H21 0.9300 C6—H6 0.9300
C22—H22 0.9300 C7—H7 0.9300
C24—C25 1.503 (4) C9—C10 1.512 (4)
C24—H24A 0.9700 C9—H9A 0.9700
C24—H24B 0.9700 C9—H9B 0.9700
C25—C26 1.373 (4) C10—C15 1.374 (4)
C25—C30 1.379 (5) C10—C11 1.378 (4)
C26—C27 1.377 (5) C11—C12 1.384 (5)
C26—H26 0.9300 C11—H11 0.9300
C27—C28 1.366 (5) C12—C13 1.364 (5)
C27—H27 0.9300 C12—H12 0.9300
C28—C29 1.355 (5) C13—C14 1.377 (5)
C28—H28 0.9300 C13—H13 0.9300
C29—C30 1.381 (5) C14—C15 1.382 (5)
C29—H29 0.9300 C14—H14 0.9300
C30—H30 0.9300 C15—H15 0.9300
C23—S3—C24 101.41 (15) C8—S1—C9 101.13 (15)
C23—N3—N4 121.2 (2) C8—N1—N2 121.0 (2)
C23—N3—H3A 119.4 C8—N1—H1 119.5
N4—N3—H3A 119.4 N2—N1—H1 119.5
C22—N4—N3 115.6 (3) C7—N2—N1 115.5 (3)
C17—C16—C21 122.5 (3) C6—C1—C2 121.8 (3)
C17—C16—Cl2 120.3 (3) C6—C1—Cl1 117.5 (3)
C21—C16—Cl2 117.3 (3) C2—C1—Cl1 120.7 (3)
C16—C17—C18 116.9 (3) C1—C2—C3 117.1 (3)
C16—C17—C22 122.2 (3) C1—C2—C7 121.8 (3)
C18—C17—C22 120.9 (3) C3—C2—C7 121.0 (3)
C19—C18—C17 120.8 (3) C4—C3—C2 121.1 (3)
C19—C18—H18 119.6 C4—C3—H3 119.5
C17—C18—H18 119.6 C2—C3—H3 119.5
C20—C19—C18 120.3 (3) C5—C4—C3 119.9 (4)
C20—C19—H19 119.9 C5—C4—H4 120.1
C18—C19—H19 119.9 C3—C4—H4 120.1
C21—C20—C19 120.5 (3) C6—C5—C4 120.6 (4)
C21—C20—H20 119.8 C6—C5—H5 119.7
C19—C20—H20 119.8 C4—C5—H5 119.7
C20—C21—C16 119.2 (3) C5—C6—C1 119.5 (4)
C20—C21—H21 120.4 C5—C6—H6 120.3
C16—C21—H21 120.4 C1—C6—H6 120.3
N4—C22—C17 121.6 (3) N2—C7—C2 120.9 (3)
N4—C22—H22 119.2 N2—C7—H7 119.6
C17—C22—H22 119.2 C2—C7—H7 119.6
N3—C23—S4 121.1 (2) N1—C8—S2 121.6 (2)
N3—C23—S3 114.0 (2) N1—C8—S1 113.4 (2)
S4—C23—S3 124.88 (19) S2—C8—S1 125.03 (19)
C25—C24—S3 108.6 (2) C10—C9—S1 108.5 (2)
C25—C24—H24A 110.0 C10—C9—H9A 110.0
S3—C24—H24A 110.0 S1—C9—H9A 110.0
C25—C24—H24B 110.0 C10—C9—H9B 110.0
S3—C24—H24B 110.0 S1—C9—H9B 110.0
H24A—C24—H24B 108.4 H9A—C9—H9B 108.4
C26—C25—C30 117.7 (3) C15—C10—C11 118.4 (3)
C26—C25—C24 121.6 (3) C15—C10—C9 121.5 (3)
C30—C25—C24 120.8 (3) C11—C10—C9 120.0 (3)
C25—C26—C27 121.3 (3) C10—C11—C12 120.4 (3)
C25—C26—H26 119.4 C10—C11—H11 119.8
C27—C26—H26 119.4 C12—C11—H11 119.8
C28—C27—C26 120.1 (3) C13—C12—C11 120.6 (3)
C28—C27—H27 119.9 C13—C12—H12 119.7
C26—C27—H27 119.9 C11—C12—H12 119.7
C29—C28—C27 119.6 (3) C12—C13—C14 119.6 (3)
C29—C28—H28 120.2 C12—C13—H13 120.2
C27—C28—H28 120.2 C14—C13—H13 120.2
C28—C29—C30 120.5 (4) C13—C14—C15 119.6 (3)
C28—C29—H29 119.8 C13—C14—H14 120.2
C30—C29—H29 119.8 C15—C14—H14 120.2
C25—C30—C29 120.9 (3) C10—C15—C14 121.3 (3)
C25—C30—H30 119.6 C10—C15—H15 119.3
C29—C30—H30 119.6 C14—C15—H15 119.3
C23—N3—N4—C22 −174.7 (3) C8—N1—N2—C7 178.3 (3)
C21—C16—C17—C18 −0.1 (5) C6—C1—C2—C3 −0.5 (5)
Cl2—C16—C17—C18 179.5 (3) Cl1—C1—C2—C3 −179.9 (3)
C21—C16—C17—C22 −178.8 (3) C6—C1—C2—C7 178.3 (3)
Cl2—C16—C17—C22 0.8 (5) Cl1—C1—C2—C7 −1.0 (4)
C16—C17—C18—C19 0.7 (5) C1—C2—C3—C4 −0.3 (5)
C22—C17—C18—C19 179.4 (3) C7—C2—C3—C4 −179.2 (3)
C17—C18—C19—C20 −0.9 (5) C2—C3—C4—C5 0.8 (6)
C18—C19—C20—C21 0.5 (6) C3—C4—C5—C6 −0.6 (6)
C19—C20—C21—C16 0.1 (6) C4—C5—C6—C1 −0.2 (6)
C17—C16—C21—C20 −0.3 (6) C2—C1—C6—C5 0.8 (6)
Cl2—C16—C21—C20 −179.9 (3) Cl1—C1—C6—C5 −179.8 (3)
N3—N4—C22—C17 179.8 (3) N1—N2—C7—C2 179.0 (3)
C16—C17—C22—N4 −176.4 (3) C1—C2—C7—N2 −174.0 (3)
C18—C17—C22—N4 5.0 (5) C3—C2—C7—N2 4.8 (5)
N4—N3—C23—S4 176.9 (2) N2—N1—C8—S2 −179.3 (2)
N4—N3—C23—S3 −2.0 (4) N2—N1—C8—S1 0.3 (4)
C24—S3—C23—N3 −179.2 (3) C9—S1—C8—N1 177.0 (2)
C24—S3—C23—S4 1.8 (3) C9—S1—C8—S2 −3.5 (3)
C23—S3—C24—C25 −174.0 (2) C8—S1—C9—C10 −174.1 (2)
S3—C24—C25—C26 −80.4 (4) S1—C9—C10—C15 71.2 (4)
S3—C24—C25—C30 99.9 (3) S1—C9—C10—C11 −110.1 (3)
C30—C25—C26—C27 0.4 (5) C15—C10—C11—C12 0.9 (5)
C24—C25—C26—C27 −179.4 (3) C9—C10—C11—C12 −177.8 (3)
C25—C26—C27—C28 0.2 (6) C10—C11—C12—C13 −0.6 (6)
C26—C27—C28—C29 −0.1 (6) C11—C12—C13—C14 0.2 (6)
C27—C28—C29—C30 −0.5 (6) C12—C13—C14—C15 −0.1 (6)
C26—C25—C30—C29 −0.9 (5) C11—C10—C15—C14 −0.9 (6)
C24—C25—C30—C29 178.8 (3) C9—C10—C15—C14 177.8 (3)
C28—C29—C30—C25 1.0 (6) C13—C14—C15—C10 0.5 (6)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N1—H1···S4 0.86 2.56 3.405 (3) 166
N3—H3A···S2 0.86 2.60 3.451 (3) 169
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2453).

References

  1. Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Ali, A. M. & Manaf, A. (2001). Inorg. Chim. Acta, 320, 1–6.
  2. Ali, M. A., Mirza, A. H., Butcher, R. J., Tarafder, M. T. H., Keat, T. B., Ali, A. M. & &Manaf, A. (2002). J. Inorg. Biochem.92, 141–148. [DOI] [PubMed]
  3. Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  4. Bruker (2005). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  5. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  6. Tarafder, M. T. H., Islam, M. T., Islam, M. A. A. A. A., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, m416–m417. [DOI] [PMC free article] [PubMed]
  7. Tarafder, M. T. H., Kasbollah, A., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2001). Polyhedron, 20, 2363–2370.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034892/cv2453sup1.cif

e-64-o2249-sup1.cif (24.1KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034892/cv2453Isup2.hkl

e-64-o2249-Isup2.hkl (270.4KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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