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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2482.
Published online 2008 November 29. doi:  10.1107/S1600536808039330
PMCID: PMC2959791

Benzyl N′-(1-methyl-1H-indol-3-yl­methyl­idene)hydrazinecarbodithio­ate

Abstract

The N′-(1-methyl-1H-indol-3-ylmethyl­idene)hydrazine­carbo­dithio­ate portion of the title mol­ecule, C18H17N3S2, is nearly planar; this unit and the phenyl ring subtend an angle of 112.9 (2)° at the methyl­ene C atom.

Related literature

For the structure of S-benzyl N-1-(1H-indol-3-ylmethyl­idenehydrazinecarbodithio­ate, see: Khaledi et al. (2008 [triangle]).

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Object name is e-64-o2482-scheme1.jpg

Experimental

Crystal data

  • C18H17N3S2
  • M r = 339.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2482-efi1.jpg
  • a = 10.6111 (4) Å
  • b = 6.1134 (2) Å
  • c = 13.4961 (4) Å
  • β = 111.934 (2)°
  • V = 812.12 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.33 mm−1
  • T = 100 (2) K
  • 0.30 × 0.10 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.908, T max = 0.993
  • 5513 measured reflections
  • 3277 independent reflections
  • 2802 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.087
  • S = 1.03
  • 3277 reflections
  • 213 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.28 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1261 Friedel pairs
  • Flack parameter: 0.01 (8)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808039330/tk2334sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808039330/tk2334Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for funding this study (Science Fund Grants 12–02-03–2031 & 12–02-03–2051).

supplementary crystallographic information

Comment

(type here to add)

Experimental

N-Methylindole-3-carbaldehyde (1.59 g, 10 mmol) and S-benzyl dithiocarbazate (1.98 g, 10 mmol) were heated in ethanol (60 ml) for 1 h. Several drops of acetic acid were added. The solution yielded a solid on cooling. This was recrystallized from DMSO.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2 times Ueq(C), 1.5 for methyl-C. The amino H-atom was located in a difference Fourier map, and was refined with a distance restraint of N–H 0.88±0.01 Å; it does not form a hydrogen bond.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of C18H17N2S3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H17N3S2F000 = 356
Mr = 339.47Dx = 1.388 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1721 reflections
a = 10.6111 (4) Åθ = 3.1–27.1º
b = 6.1134 (2) ŵ = 0.33 mm1
c = 13.4961 (4) ÅT = 100 (2) K
β = 111.934 (2)ºPlate, yellow
V = 812.12 (5) Å30.30 × 0.10 × 0.02 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer3277 independent reflections
Radiation source: fine-focus sealed tube2802 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.6º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −13→13
Tmin = 0.908, Tmax = 0.993k = −6→7
5513 measured reflectionsl = −17→17

Refinement

Refinement on F2Hydrogen site location: constr
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.037  w = 1/[σ2(Fo2) + (0.0366P)2 + 0.212P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.087(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.28 e Å3
3277 reflectionsΔρmin = −0.28 e Å3
213 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), 1261 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.01 (8)
Secondary atom site location: difference Fourier map

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.33191 (7)0.50000 (12)0.67816 (5)0.01960 (16)
S20.48123 (7)0.86601 (13)0.61270 (5)0.02642 (18)
N10.2902 (2)0.7662 (4)1.16590 (16)0.0202 (5)
N20.3791 (2)0.7502 (4)0.85695 (16)0.0181 (5)
N30.4323 (2)0.8477 (4)0.78860 (16)0.0183 (5)
H30.480 (3)0.967 (3)0.796 (2)0.035 (9)*
C10.2337 (3)0.5789 (5)1.1079 (2)0.0178 (6)
C20.1584 (3)0.4147 (5)1.1303 (2)0.0215 (6)
H20.14220.41431.19500.026*
C30.1075 (3)0.2515 (5)1.0548 (2)0.0236 (6)
H3A0.05310.13891.06680.028*
C40.1347 (3)0.2496 (5)0.9610 (2)0.0215 (6)
H40.09830.13540.91060.026*
C50.2133 (3)0.4101 (4)0.9399 (2)0.0193 (6)
H50.23260.40510.87670.023*
C60.2637 (3)0.5795 (4)1.01374 (19)0.0166 (6)
C70.2743 (3)0.8324 (5)1.2645 (2)0.0261 (7)
H7A0.31620.97611.28670.039*
H7B0.31860.72491.32060.039*
H7C0.17740.84051.25240.039*
C80.3524 (3)0.8815 (5)1.11224 (19)0.0201 (6)
H80.39811.01661.13570.024*
C90.3409 (3)0.7767 (4)1.01840 (19)0.0168 (6)
C100.3932 (2)0.8586 (5)0.94249 (18)0.0166 (5)
H100.43920.99520.95510.020*
C110.4177 (3)0.7519 (5)0.6953 (2)0.0197 (6)
C120.3161 (3)0.4207 (5)0.54473 (19)0.0229 (6)
H12A0.38400.50190.52510.028*
H12B0.33660.26270.54450.028*
C130.1765 (3)0.4642 (5)0.46213 (19)0.0192 (6)
C140.1145 (3)0.6657 (5)0.4536 (2)0.0220 (6)
H140.16060.78000.50100.026*
C15−0.0137 (3)0.7043 (5)0.3773 (2)0.0258 (7)
H15−0.05500.84380.37260.031*
C16−0.0816 (3)0.5379 (6)0.3078 (2)0.0295 (8)
H16−0.16930.56380.25520.035*
C17−0.0220 (3)0.3353 (5)0.3150 (2)0.0280 (7)
H17−0.06860.22120.26770.034*
C180.1073 (3)0.2984 (5)0.3919 (2)0.0240 (7)
H180.14860.15890.39660.029*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0229 (3)0.0209 (4)0.0149 (3)−0.0023 (3)0.0070 (2)0.0006 (3)
S20.0317 (4)0.0286 (4)0.0252 (3)−0.0013 (4)0.0179 (3)0.0058 (3)
N10.0225 (12)0.0243 (13)0.0158 (10)0.0007 (10)0.0094 (9)−0.0026 (9)
N20.0191 (11)0.0187 (13)0.0176 (10)−0.0022 (10)0.0082 (9)0.0036 (9)
N30.0232 (12)0.0166 (13)0.0178 (10)−0.0018 (10)0.0109 (9)0.0023 (10)
C10.0179 (14)0.0190 (15)0.0159 (12)0.0050 (12)0.0056 (11)0.0017 (11)
C20.0210 (14)0.0248 (17)0.0208 (13)0.0049 (12)0.0103 (11)0.0051 (11)
C30.0217 (14)0.0195 (16)0.0298 (14)−0.0007 (13)0.0097 (12)0.0052 (12)
C40.0225 (14)0.0195 (15)0.0208 (13)−0.0007 (12)0.0062 (11)−0.0012 (12)
C50.0192 (13)0.0213 (16)0.0178 (12)0.0031 (12)0.0072 (11)0.0025 (11)
C60.0145 (13)0.0187 (15)0.0169 (12)0.0041 (11)0.0063 (10)0.0031 (11)
C70.0369 (17)0.0297 (18)0.0160 (12)0.0016 (14)0.0148 (12)−0.0056 (12)
C80.0173 (13)0.0194 (15)0.0216 (12)0.0007 (13)0.0049 (10)−0.0003 (12)
C90.0156 (13)0.0182 (15)0.0157 (12)0.0003 (11)0.0048 (10)0.0016 (11)
C100.0180 (13)0.0136 (13)0.0168 (11)−0.0014 (12)0.0049 (10)−0.0002 (11)
C110.0176 (13)0.0225 (16)0.0185 (12)0.0038 (12)0.0061 (11)0.0040 (11)
C120.0298 (15)0.0225 (16)0.0182 (12)0.0035 (12)0.0109 (12)−0.0016 (11)
C130.0230 (13)0.0242 (17)0.0130 (11)−0.0008 (12)0.0099 (10)0.0005 (11)
C140.0230 (15)0.0266 (17)0.0157 (12)−0.0016 (12)0.0064 (11)−0.0021 (11)
C150.0281 (16)0.0256 (17)0.0254 (14)0.0045 (13)0.0122 (12)0.0060 (13)
C160.0244 (15)0.044 (2)0.0176 (12)−0.0029 (14)0.0055 (11)0.0064 (13)
C170.0353 (17)0.0324 (19)0.0169 (12)−0.0157 (15)0.0105 (12)−0.0049 (13)
C180.0366 (17)0.0196 (16)0.0202 (13)−0.0043 (13)0.0159 (13)−0.0011 (11)

Geometric parameters (Å, °)

S1—C111.759 (3)C7—H7A0.9800
S1—C121.811 (3)C7—H7B0.9800
S2—C111.657 (3)C7—H7C0.9800
N1—C81.347 (3)C8—C91.383 (4)
N1—C11.390 (4)C8—H80.9500
N1—C71.460 (3)C9—C101.426 (4)
N2—C101.290 (3)C10—H100.9500
N2—N31.384 (3)C12—C131.508 (4)
N3—C111.345 (3)C12—H12A0.9900
N3—H30.875 (10)C12—H12B0.9900
C1—C21.386 (4)C13—C141.381 (4)
C1—C61.420 (4)C13—C181.394 (4)
C2—C31.384 (4)C14—C151.386 (4)
C2—H20.9500C14—H140.9500
C3—C41.400 (4)C15—C161.389 (4)
C3—H3A0.9500C15—H150.9500
C4—C51.385 (4)C16—C171.378 (5)
C4—H40.9500C16—H160.9500
C5—C61.398 (4)C17—C181.395 (4)
C5—H50.9500C17—H170.9500
C6—C91.445 (4)C18—H180.9500
C11—S1—C12102.48 (13)C9—C8—H8124.6
C8—N1—C1108.8 (2)C8—C9—C10124.8 (3)
C8—N1—C7126.3 (3)C8—C9—C6106.3 (2)
C1—N1—C7124.7 (2)C10—C9—C6128.9 (2)
C10—N2—N3115.8 (2)N2—C10—C9121.1 (3)
C11—N3—N2120.3 (2)N2—C10—H10119.5
C11—N3—H3109 (2)C9—C10—H10119.5
N2—N3—H3131 (2)N3—C11—S2120.9 (2)
C2—C1—N1129.5 (2)N3—C11—S1112.2 (2)
C2—C1—C6122.6 (3)S2—C11—S1126.94 (17)
N1—C1—C6108.0 (2)C13—C12—S1112.87 (19)
C3—C2—C1117.4 (2)C13—C12—H12A109.0
C3—C2—H2121.3S1—C12—H12A109.0
C1—C2—H2121.3C13—C12—H12B109.0
C2—C3—C4121.1 (3)S1—C12—H12B109.0
C2—C3—H3A119.4H12A—C12—H12B107.8
C4—C3—H3A119.4C14—C13—C18118.6 (2)
C5—C4—C3121.6 (3)C14—C13—C12121.6 (2)
C5—C4—H4119.2C18—C13—C12119.8 (3)
C3—C4—H4119.2C13—C14—C15121.2 (3)
C4—C5—C6118.6 (2)C13—C14—H14119.4
C4—C5—H5120.7C15—C14—H14119.4
C6—C5—H5120.7C14—C15—C16119.7 (3)
C5—C6—C1118.8 (2)C14—C15—H15120.2
C5—C6—C9135.2 (2)C16—C15—H15120.2
C1—C6—C9106.0 (2)C17—C16—C15120.2 (3)
N1—C7—H7A109.5C17—C16—H16119.9
N1—C7—H7B109.5C15—C16—H16119.9
H7A—C7—H7B109.5C16—C17—C18119.7 (3)
N1—C7—H7C109.5C16—C17—H17120.2
H7A—C7—H7C109.5C18—C17—H17120.2
H7B—C7—H7C109.5C13—C18—C17120.7 (3)
N1—C8—C9110.9 (3)C13—C18—H18119.7
N1—C8—H8124.6C17—C18—H18119.7
C10—N2—N3—C11−177.2 (2)C1—C6—C9—C8−0.2 (3)
C8—N1—C1—C2−178.6 (3)C5—C6—C9—C10−1.0 (5)
C7—N1—C1—C2−3.0 (4)C1—C6—C9—C10−178.3 (3)
C8—N1—C1—C60.3 (3)N3—N2—C10—C9179.1 (2)
C7—N1—C1—C6175.9 (2)C8—C9—C10—N2179.5 (3)
N1—C1—C2—C3176.3 (3)C6—C9—C10—N2−2.7 (4)
C6—C1—C2—C3−2.4 (4)N2—N3—C11—S2−179.82 (19)
C1—C2—C3—C41.8 (4)N2—N3—C11—S1−1.8 (3)
C2—C3—C4—C50.0 (4)C12—S1—C11—N3175.97 (19)
C3—C4—C5—C6−1.3 (4)C12—S1—C11—S2−6.1 (2)
C4—C5—C6—C10.8 (4)C11—S1—C12—C13−101.3 (2)
C4—C5—C6—C9−176.2 (3)S1—C12—C13—C1450.8 (3)
C2—C1—C6—C51.1 (4)S1—C12—C13—C18−129.3 (2)
N1—C1—C6—C5−177.9 (2)C18—C13—C14—C150.0 (4)
C2—C1—C6—C9178.9 (2)C12—C13—C14—C15179.9 (2)
N1—C1—C6—C9−0.1 (3)C13—C14—C15—C16−0.1 (4)
C1—N1—C8—C9−0.4 (3)C14—C15—C16—C170.3 (4)
C7—N1—C8—C9−175.9 (3)C15—C16—C17—C18−0.4 (4)
N1—C8—C9—C10178.6 (2)C14—C13—C18—C17−0.2 (4)
N1—C8—C9—C60.4 (3)C12—C13—C18—C17180.0 (2)
C5—C6—C9—C8177.1 (3)C16—C17—C18—C130.4 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2334).

References

  • Barbour, L. J. (2001). J. Supramol. Chem 1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2107. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

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