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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2249.
Published online 2008 November 8. doi:  10.1107/S1600536808034892
PMCID: PMC2960048

Benzyl N′-(2-chloro­benzyl­idene)hydrazinecarbodithio­ate

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 [triangle], 2002 [triangle]); Tarafder et al. (2001 [triangle], 2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-64-o2249-scheme1.jpg

Experimental

Crystal data

  • C15H13ClN2S2
  • M r = 320.84
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2249-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: APEX2 and SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL .

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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

Crystal data

C15H13ClN2S2Z = 4
Mr = 320.84F000 = 664
Triclinic, P1Dx = 1.359 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 11.877 (2) ÅCell parameters from 1618 reflections
b = 11.906 (2) Åθ = 2.6–24.6º
c = 12.623 (3) ŵ = 0.50 mm1
α = 68.242 (3)ºT = 295 (2) K
β = 71.116 (4)ºBlock, yellow
γ = 82.335 (4)º0.12 × 0.10 × 0.06 mm
V = 1568.4 (5) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer5524 independent reflections
Radiation source: fine-focus sealed tube3436 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 295(2) Kθmax = 25.1º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 2005)h = −11→14
Tmin = 0.942, Tmax = 0.971k = −14→13
8397 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-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 reflectionsΔρmax = 0.44 e Å3
361 parametersΔρmin = −0.46 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
Cl20.61916 (10)0.15814 (11)0.57081 (9)0.0994 (4)
S30.36389 (7)0.66976 (8)0.21058 (7)0.0541 (3)
S40.15028 (7)0.61729 (8)0.43141 (7)0.0566 (3)
N30.3563 (2)0.5043 (2)0.4167 (2)0.0514 (7)
H3A0.32700.46340.49140.062*
N40.4704 (2)0.4789 (2)0.3570 (2)0.0478 (7)
C160.6959 (3)0.2483 (3)0.4266 (3)0.0544 (9)
C170.6419 (3)0.3506 (3)0.3648 (3)0.0455 (8)
C180.7096 (3)0.4188 (3)0.2498 (3)0.0554 (9)
H180.67700.48880.20560.066*
C190.8242 (3)0.3835 (3)0.2014 (3)0.0606 (10)
H190.86780.42900.12440.073*
C200.8742 (3)0.2812 (4)0.2663 (3)0.0617 (10)
H200.95180.25840.23320.074*
C210.8112 (3)0.2133 (3)0.3785 (3)0.0631 (10)
H210.84520.14430.42240.076*
C220.5211 (3)0.3882 (3)0.4168 (3)0.0504 (8)
H220.48020.34490.49550.061*
C230.2902 (3)0.5914 (3)0.3608 (3)0.0441 (8)
C240.2502 (3)0.7786 (3)0.1668 (3)0.0612 (10)
H24A0.17720.73720.18610.073*
H24B0.23350.83470.20970.073*
C250.2944 (3)0.8461 (3)0.0345 (3)0.0480 (8)
C260.3717 (3)0.9404 (3)−0.0123 (3)0.0609 (10)
H260.39810.96280.03890.073*
C270.4111 (3)1.0026 (3)−0.1335 (3)0.0689 (11)
H270.46361.0661−0.16340.083*
C280.3730 (3)0.9712 (4)−0.2098 (3)0.0684 (11)
H280.39941.0132−0.29160.082*
C290.2967 (3)0.8785 (4)−0.1655 (3)0.0716 (11)
H290.27020.8573−0.21720.086*
C300.2579 (3)0.8152 (3)−0.0442 (3)0.0623 (10)
H300.20650.7509−0.01510.075*
Cl1−0.22425 (9)0.74778 (9)0.55632 (8)0.0702 (3)
S10.06032 (8)0.28590 (8)0.93397 (7)0.0589 (3)
S20.25595 (8)0.30266 (9)0.70505 (7)0.0619 (3)
N10.0603 (2)0.4336 (2)0.7232 (2)0.0497 (7)
H10.08570.46790.64690.060*
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)
H3−0.22690.50020.95040.069*
C4−0.3772 (3)0.5999 (4)0.9548 (3)0.0728 (11)
H4−0.40980.57081.03750.087*
C5−0.4383 (3)0.6844 (4)0.8849 (4)0.0804 (13)
H5−0.51280.71180.92050.097*
C6−0.3909 (3)0.7286 (4)0.7634 (3)0.0669 (10)
H6−0.43290.78570.71640.080*
C7−0.1006 (3)0.5565 (3)0.7233 (3)0.0461 (8)
H7−0.06520.59100.64130.055*
C80.1257 (3)0.3461 (3)0.7791 (3)0.0446 (8)
C90.1668 (3)0.1677 (3)0.9769 (3)0.0613 (10)
H9A0.18020.11500.93080.074*
H9B0.24210.20300.96140.074*
C100.1176 (3)0.0961 (3)1.1086 (3)0.0476 (8)
C110.1692 (3)0.1043 (3)1.1888 (3)0.0572 (9)
H110.23250.15611.16200.069*
C120.1273 (3)0.0359 (3)1.3090 (3)0.0639 (10)
H120.16320.04151.36220.077*
C130.0338 (3)−0.0398 (3)1.3501 (3)0.0632 (10)
H130.0060−0.08541.43100.076*
C14−0.0190 (3)−0.0484 (3)1.2711 (3)0.0672 (11)
H14−0.0827−0.09991.29830.081*
C150.0231 (3)0.0200 (3)1.1512 (3)0.0617 (10)
H15−0.01320.01441.09820.074*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl20.0801 (8)0.0990 (9)0.0654 (7)0.0195 (6)−0.0101 (6)0.0142 (6)
S30.0454 (5)0.0542 (6)0.0410 (5)0.0071 (4)−0.0009 (4)−0.0054 (4)
S40.0451 (5)0.0626 (6)0.0416 (5)0.0100 (4)−0.0017 (4)−0.0085 (4)
N30.0410 (16)0.0570 (18)0.0386 (15)0.0077 (13)−0.0044 (12)−0.0063 (13)
N40.0396 (15)0.0508 (17)0.0441 (16)0.0053 (13)−0.0071 (13)−0.0135 (13)
C160.046 (2)0.064 (2)0.0444 (19)0.0060 (17)−0.0116 (16)−0.0131 (17)
C170.0387 (18)0.050 (2)0.0456 (18)0.0053 (15)−0.0141 (15)−0.0155 (16)
C180.051 (2)0.056 (2)0.054 (2)0.0006 (17)−0.0130 (17)−0.0162 (17)
C190.056 (2)0.069 (3)0.052 (2)−0.005 (2)−0.0029 (18)−0.0267 (19)
C200.045 (2)0.077 (3)0.070 (3)0.012 (2)−0.0156 (19)−0.040 (2)
C210.057 (2)0.071 (3)0.063 (2)0.019 (2)−0.027 (2)−0.025 (2)
C220.047 (2)0.052 (2)0.0402 (18)0.0013 (17)−0.0081 (16)−0.0086 (16)
C230.0441 (18)0.0427 (19)0.0399 (17)0.0017 (15)−0.0081 (15)−0.0126 (15)
C240.049 (2)0.059 (2)0.051 (2)0.0140 (17)−0.0038 (17)−0.0065 (17)
C250.0372 (18)0.045 (2)0.0478 (19)0.0061 (15)−0.0070 (15)−0.0073 (16)
C260.064 (2)0.065 (2)0.051 (2)−0.010 (2)−0.0216 (18)−0.0108 (19)
C270.073 (3)0.062 (3)0.057 (2)−0.020 (2)−0.014 (2)−0.002 (2)
C280.064 (2)0.075 (3)0.048 (2)0.002 (2)−0.0136 (19)−0.004 (2)
C290.064 (2)0.093 (3)0.060 (2)0.000 (2)−0.026 (2)−0.024 (2)
C300.044 (2)0.060 (2)0.077 (3)−0.0071 (18)−0.0144 (19)−0.019 (2)
Cl10.0795 (7)0.0724 (7)0.0449 (5)0.0055 (5)−0.0195 (5)−0.0065 (4)
S10.0544 (5)0.0630 (6)0.0368 (5)0.0098 (4)−0.0037 (4)−0.0044 (4)
S20.0575 (6)0.0645 (6)0.0414 (5)0.0168 (5)−0.0038 (4)−0.0092 (4)
N10.0471 (16)0.0566 (18)0.0324 (14)0.0087 (14)−0.0064 (12)−0.0090 (13)
N20.0382 (15)0.0541 (17)0.0400 (15)0.0016 (13)−0.0064 (12)−0.0133 (13)
C10.050 (2)0.053 (2)0.0430 (19)0.0028 (17)−0.0150 (16)−0.0158 (16)
C20.0414 (18)0.048 (2)0.0406 (18)−0.0013 (15)−0.0083 (15)−0.0144 (15)
C30.056 (2)0.061 (2)0.045 (2)0.0045 (18)−0.0118 (17)−0.0111 (17)
C40.058 (2)0.092 (3)0.049 (2)0.005 (2)−0.0011 (19)−0.019 (2)
C50.050 (2)0.108 (4)0.075 (3)0.021 (2)−0.010 (2)−0.038 (3)
C60.057 (2)0.078 (3)0.065 (3)0.019 (2)−0.025 (2)−0.025 (2)
C70.0427 (18)0.050 (2)0.0369 (17)0.0004 (16)−0.0086 (15)−0.0086 (15)
C80.0452 (18)0.0440 (19)0.0380 (17)0.0020 (15)−0.0105 (15)−0.0095 (15)
C90.059 (2)0.061 (2)0.044 (2)0.0099 (18)−0.0101 (17)−0.0044 (17)
C100.053 (2)0.044 (2)0.0389 (17)0.0089 (16)−0.0134 (16)−0.0101 (15)
C110.065 (2)0.049 (2)0.053 (2)−0.0041 (18)−0.0205 (18)−0.0095 (17)
C120.076 (3)0.070 (3)0.047 (2)0.009 (2)−0.026 (2)−0.0189 (19)
C130.077 (3)0.060 (2)0.0364 (19)0.010 (2)−0.0092 (19)−0.0085 (17)
C140.066 (2)0.065 (3)0.055 (2)−0.011 (2)−0.007 (2)−0.011 (2)
C150.066 (2)0.069 (3)0.050 (2)−0.003 (2)−0.0174 (19)−0.0199 (19)

Geometric parameters (Å, °)

Cl2—C161.742 (3)Cl1—C11.738 (3)
S3—C231.750 (3)S1—C81.751 (3)
S3—C241.815 (3)S1—C91.810 (3)
S4—C231.662 (3)S2—C81.657 (3)
N3—C231.337 (4)N1—C81.334 (4)
N3—N41.376 (3)N1—N21.375 (3)
N3—H3A0.8600N1—H10.8600
N4—C221.271 (4)N2—C71.279 (4)
C16—C171.384 (4)C1—C61.377 (5)
C16—C211.384 (5)C1—C21.390 (4)
C17—C181.399 (4)C2—C31.398 (4)
C17—C221.458 (4)C2—C71.455 (4)
C18—C191.380 (5)C3—C41.376 (5)
C18—H180.9300C3—H30.9300
C19—C201.375 (5)C4—C51.371 (5)
C19—H190.9300C4—H40.9300
C20—C211.358 (5)C5—C61.366 (5)
C20—H200.9300C5—H50.9300
C21—H210.9300C6—H60.9300
C22—H220.9300C7—H70.9300
C24—C251.503 (4)C9—C101.512 (4)
C24—H24A0.9700C9—H9A0.9700
C24—H24B0.9700C9—H9B0.9700
C25—C261.373 (4)C10—C151.374 (4)
C25—C301.379 (5)C10—C111.378 (4)
C26—C271.377 (5)C11—C121.384 (5)
C26—H260.9300C11—H110.9300
C27—C281.366 (5)C12—C131.364 (5)
C27—H270.9300C12—H120.9300
C28—C291.355 (5)C13—C141.377 (5)
C28—H280.9300C13—H130.9300
C29—C301.381 (5)C14—C151.382 (5)
C29—H290.9300C14—H140.9300
C30—H300.9300C15—H150.9300
C23—S3—C24101.41 (15)C8—S1—C9101.13 (15)
C23—N3—N4121.2 (2)C8—N1—N2121.0 (2)
C23—N3—H3A119.4C8—N1—H1119.5
N4—N3—H3A119.4N2—N1—H1119.5
C22—N4—N3115.6 (3)C7—N2—N1115.5 (3)
C17—C16—C21122.5 (3)C6—C1—C2121.8 (3)
C17—C16—Cl2120.3 (3)C6—C1—Cl1117.5 (3)
C21—C16—Cl2117.3 (3)C2—C1—Cl1120.7 (3)
C16—C17—C18116.9 (3)C1—C2—C3117.1 (3)
C16—C17—C22122.2 (3)C1—C2—C7121.8 (3)
C18—C17—C22120.9 (3)C3—C2—C7121.0 (3)
C19—C18—C17120.8 (3)C4—C3—C2121.1 (3)
C19—C18—H18119.6C4—C3—H3119.5
C17—C18—H18119.6C2—C3—H3119.5
C20—C19—C18120.3 (3)C5—C4—C3119.9 (4)
C20—C19—H19119.9C5—C4—H4120.1
C18—C19—H19119.9C3—C4—H4120.1
C21—C20—C19120.5 (3)C6—C5—C4120.6 (4)
C21—C20—H20119.8C6—C5—H5119.7
C19—C20—H20119.8C4—C5—H5119.7
C20—C21—C16119.2 (3)C5—C6—C1119.5 (4)
C20—C21—H21120.4C5—C6—H6120.3
C16—C21—H21120.4C1—C6—H6120.3
N4—C22—C17121.6 (3)N2—C7—C2120.9 (3)
N4—C22—H22119.2N2—C7—H7119.6
C17—C22—H22119.2C2—C7—H7119.6
N3—C23—S4121.1 (2)N1—C8—S2121.6 (2)
N3—C23—S3114.0 (2)N1—C8—S1113.4 (2)
S4—C23—S3124.88 (19)S2—C8—S1125.03 (19)
C25—C24—S3108.6 (2)C10—C9—S1108.5 (2)
C25—C24—H24A110.0C10—C9—H9A110.0
S3—C24—H24A110.0S1—C9—H9A110.0
C25—C24—H24B110.0C10—C9—H9B110.0
S3—C24—H24B110.0S1—C9—H9B110.0
H24A—C24—H24B108.4H9A—C9—H9B108.4
C26—C25—C30117.7 (3)C15—C10—C11118.4 (3)
C26—C25—C24121.6 (3)C15—C10—C9121.5 (3)
C30—C25—C24120.8 (3)C11—C10—C9120.0 (3)
C25—C26—C27121.3 (3)C10—C11—C12120.4 (3)
C25—C26—H26119.4C10—C11—H11119.8
C27—C26—H26119.4C12—C11—H11119.8
C28—C27—C26120.1 (3)C13—C12—C11120.6 (3)
C28—C27—H27119.9C13—C12—H12119.7
C26—C27—H27119.9C11—C12—H12119.7
C29—C28—C27119.6 (3)C12—C13—C14119.6 (3)
C29—C28—H28120.2C12—C13—H13120.2
C27—C28—H28120.2C14—C13—H13120.2
C28—C29—C30120.5 (4)C13—C14—C15119.6 (3)
C28—C29—H29119.8C13—C14—H14120.2
C30—C29—H29119.8C15—C14—H14120.2
C25—C30—C29120.9 (3)C10—C15—C14121.3 (3)
C25—C30—H30119.6C10—C15—H15119.3
C29—C30—H30119.6C14—C15—H15119.3
C23—N3—N4—C22−174.7 (3)C8—N1—N2—C7178.3 (3)
C21—C16—C17—C18−0.1 (5)C6—C1—C2—C3−0.5 (5)
Cl2—C16—C17—C18179.5 (3)Cl1—C1—C2—C3−179.9 (3)
C21—C16—C17—C22−178.8 (3)C6—C1—C2—C7178.3 (3)
Cl2—C16—C17—C220.8 (5)Cl1—C1—C2—C7−1.0 (4)
C16—C17—C18—C190.7 (5)C1—C2—C3—C4−0.3 (5)
C22—C17—C18—C19179.4 (3)C7—C2—C3—C4−179.2 (3)
C17—C18—C19—C20−0.9 (5)C2—C3—C4—C50.8 (6)
C18—C19—C20—C210.5 (6)C3—C4—C5—C6−0.6 (6)
C19—C20—C21—C160.1 (6)C4—C5—C6—C1−0.2 (6)
C17—C16—C21—C20−0.3 (6)C2—C1—C6—C50.8 (6)
Cl2—C16—C21—C20−179.9 (3)Cl1—C1—C6—C5−179.8 (3)
N3—N4—C22—C17179.8 (3)N1—N2—C7—C2179.0 (3)
C16—C17—C22—N4−176.4 (3)C1—C2—C7—N2−174.0 (3)
C18—C17—C22—N45.0 (5)C3—C2—C7—N24.8 (5)
N4—N3—C23—S4176.9 (2)N2—N1—C8—S2−179.3 (2)
N4—N3—C23—S3−2.0 (4)N2—N1—C8—S10.3 (4)
C24—S3—C23—N3−179.2 (3)C9—S1—C8—N1177.0 (2)
C24—S3—C23—S41.8 (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—C1571.2 (4)
S3—C24—C25—C3099.9 (3)S1—C9—C10—C11−110.1 (3)
C30—C25—C26—C270.4 (5)C15—C10—C11—C120.9 (5)
C24—C25—C26—C27−179.4 (3)C9—C10—C11—C12−177.8 (3)
C25—C26—C27—C280.2 (6)C10—C11—C12—C13−0.6 (6)
C26—C27—C28—C29−0.1 (6)C11—C12—C13—C140.2 (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—C29178.8 (3)C9—C10—C15—C14177.8 (3)
C28—C29—C30—C251.0 (6)C13—C14—C15—C100.5 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···S40.862.563.405 (3)166
N3—H3A···S20.862.603.451 (3)169

Footnotes

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

References

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