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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Nov 26;64(Pt 12):o2430. doi: 10.1107/S1600536808038579

Benzyl N′-(1-methyl-1H-indol-2-ylmethyl­ene)hydrazinecarbodithio­ate

Hamid Khaledi a, Hapipah Mohd Ali a, Seik Weng Ng a,*
PMCID: PMC2960023  PMID: 21581398

Abstract

In the title compound, C18H17N3S2, the dihedral angle between the planes of the aromatic ring systems is 83.63 (16)°. In the crystal structure, inversion dimers occur, linked by pairs of N—H⋯S hydrogen bonds.

Related literature

For the crystal structures of the benzyl esters of hydrazinecarbodithioic acids, see: Ali et al. (2004 ▶); Chan et al. (2003 ▶); Fun et al. (1995 ▶); How et al. (2007 ▶); Khoo et al. (2005 ▶); Qiu & Luo (2007 ▶); Roy et al. (2007 ▶); Tarafder et al. (2002 ▶); Xu et al. (1991 ▶, 2002 ▶); Zhang et al. (2004 ▶).graphic file with name e-64-o2430-scheme1.jpg

Experimental

Crystal data

  • C18H17N3S2

  • M r = 339.47

  • Triclinic, Inline graphic

  • a = 5.1203 (1) Å

  • b = 11.9377 (3) Å

  • c = 14.1936 (4) Å

  • α = 108.203 (2)°

  • β = 90.230 (2)°

  • γ = 96.191 (2)°

  • V = 818.70 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.33 mm−1

  • T = 100 (2) K

  • 0.40 × 0.08 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.880, T max = 0.987

  • 7605 measured reflections

  • 3732 independent reflections

  • 2653 reflections with I > 2σ(I)

  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.075

  • wR(F 2) = 0.225

  • S = 1.13

  • 3732 reflections

  • 209 parameters

  • H-atom parameters constrained

  • Δρmax = 1.56 e Å−3

  • Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: pubCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038579/hb2848sup1.cif

e-64-o2430-sup1.cif (17.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038579/hb2848Isup2.hkl

e-64-o2430-Isup2.hkl (182.9KB, 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⋯S2i 0.88 2.49 3.336 (3) 161
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Symmetry code: (i) Inline graphic.

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

For related structures, see: Ali et al. (2004); Chan et al. (2003); Fun et al. (1995); How et al. (2007); Khoo et al. (2005); Qiu & Luo (2007); Roy et al. (2007); Tarafder et al. (2002); Xu et al. (1991, 2002); Zhang et al. (2004).

Experimental

1-Methylindole-2-carbaldehyde (0.40 g, 2.5 mmol) and S-benzyldithiocarbazate (0.50 g, 2.5 mmol) were heated in ethanol (40 ml) for 3 h. The solid that separated on cooling the solution was collected and recrystallized from ethanol and washed with cold ethanol and dried. Orange prisms of (I) were grown by slow evaporation of ethanol solution at room temperature.

Refinement

Hydrogen atoms were placed at calculated positions (C–H = 0.95–0.99, N–H = 0.88Å) and refined as riding with U(H) = 1.2–1.5 times Ueq(C,N).

The largest difference peak is close to S2.

Figures

Fig. 1.

Fig. 1.

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The molecular structue of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C18H17N3S2 Z = 2
Mr = 339.47 F000 = 356
Triclinic, P1 Dx = 1.377 Mg m−3
Hall symbol: -P 1 Mo Kα radiation λ = 0.71073 Å
a = 5.1203 (1) Å Cell parameters from 2060 reflections
b = 11.9377 (3) Å θ = 2.6–28.1º
c = 14.1936 (4) Å µ = 0.33 mm−1
α = 108.203 (2)º T = 100 (2) K
β = 90.230 (2)º Prism, orange
γ = 96.191 (2)º 0.40 × 0.08 × 0.04 mm
V = 818.70 (3) Å3
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Data collection

Bruker SMART APEX diffractometer 3732 independent reflections
Radiation source: fine-focus sealed tube 2653 reflections with I > 2σ(I)
Monochromator: graphite Rint = 0.047
T = 100(2) K θmax = 27.5º
ω scans θmin = 1.5º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996) h = −6→6
Tmin = 0.880, Tmax = 0.987 k = −15→15
7605 measured reflections l = −18→18
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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)] = 0.075 H-atom parameters constrained
wR(F2) = 0.225   w = 1/[σ2(Fo2) + (0.1301P)2 + 0.2413P] where P = (Fo2 + 2Fc2)/3
S = 1.13 (Δ/σ)max = 0.001
3732 reflections Δρmax = 1.56 e Å−3
209 parameters Δρmin = −0.59 e Å−3
Primary atom site location: structure-invariant direct methods Extinction correction: none
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
S1 0.58962 (17) 0.85808 (8) 0.65532 (7) 0.0205 (3)
S2 0.72855 (18) 0.65218 (8) 0.48348 (7) 0.0221 (3)
N1 0.3474 (6) 0.6436 (3) 0.6054 (2) 0.0201 (7)
H1 0.3089 0.5687 0.5697 0.024*
N2 0.2021 (6) 0.6924 (3) 0.6868 (2) 0.0195 (7)
N3 −0.1582 (6) 0.7565 (3) 0.8569 (2) 0.0184 (7)
C1 0.9083 (7) 1.0499 (3) 0.6464 (3) 0.0215 (8)
C2 1.1083 (7) 1.1026 (3) 0.7164 (3) 0.0220 (8)
H2 1.2181 1.0543 0.7367 0.026*
C3 1.1524 (7) 1.2255 (4) 0.7581 (3) 0.0225 (8)
H3 1.2914 1.2608 0.8062 0.027*
C4 0.9918 (7) 1.2961 (3) 0.7288 (3) 0.0220 (8)
H4 1.0218 1.3801 0.7563 0.026*
C5 0.7885 (8) 1.2441 (4) 0.6596 (3) 0.0245 (8)
H5 0.6772 1.2924 0.6402 0.029*
C6 0.7460 (7) 1.1216 (4) 0.6183 (3) 0.0245 (8)
H6 0.6058 1.0864 0.5707 0.029*
C7 0.8657 (7) 0.9171 (3) 0.5981 (3) 0.0241 (8)
H7A 1.0257 0.8814 0.6075 0.029*
H7B 0.8278 0.8978 0.5260 0.029*
C8 0.5454 (7) 0.7094 (3) 0.5804 (3) 0.0172 (7)
C9 0.0151 (7) 0.6197 (3) 0.7016 (3) 0.0207 (8)
H9 −0.0098 0.5417 0.6557 0.025*
C10 −0.1597 (7) 0.6484 (3) 0.7829 (3) 0.0188 (8)
C11 0.0120 (8) 0.8667 (3) 0.8688 (3) 0.0256 (9)
H11A 0.1053 0.8922 0.9337 0.038*
H11B −0.0949 0.9284 0.8643 0.038*
H11C 0.1397 0.8536 0.8163 0.038*
C12 −0.3503 (7) 0.7444 (3) 0.9212 (3) 0.0194 (8)
C13 −0.4243 (8) 0.8289 (4) 1.0078 (3) 0.0240 (8)
H13 −0.3371 0.9075 1.0304 0.029*
C14 −0.6278 (8) 0.7930 (4) 1.0584 (3) 0.0268 (9)
H14 −0.6825 0.8482 1.1170 0.032*
C15 −0.7569 (8) 0.6772 (4) 1.0260 (3) 0.0289 (9)
H15 −0.8972 0.6556 1.0628 0.035*
C16 −0.6840 (8) 0.5941 (4) 0.9418 (3) 0.0273 (9)
H16 −0.7720 0.5157 0.9206 0.033*
C17 −0.4769 (7) 0.6274 (3) 0.8878 (3) 0.0206 (8)
C18 −0.3533 (7) 0.5682 (3) 0.8002 (3) 0.0218 (8)
H18 −0.3958 0.4877 0.7605 0.026*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0212 (5) 0.0153 (5) 0.0253 (5) 0.0064 (3) 0.0069 (4) 0.0053 (4)
S2 0.0263 (5) 0.0180 (5) 0.0230 (5) 0.0078 (4) 0.0098 (4) 0.0060 (4)
N1 0.0221 (15) 0.0163 (15) 0.0211 (16) 0.0058 (12) 0.0055 (13) 0.0034 (12)
N2 0.0221 (15) 0.0181 (16) 0.0211 (16) 0.0090 (12) 0.0056 (13) 0.0081 (13)
N3 0.0220 (15) 0.0131 (15) 0.0230 (16) 0.0065 (12) 0.0057 (13) 0.0081 (12)
C1 0.0207 (18) 0.0182 (19) 0.027 (2) 0.0074 (14) 0.0118 (15) 0.0076 (15)
C2 0.0193 (18) 0.0203 (19) 0.030 (2) 0.0093 (14) 0.0061 (15) 0.0101 (16)
C3 0.0194 (18) 0.023 (2) 0.025 (2) 0.0051 (14) 0.0031 (15) 0.0075 (16)
C4 0.0253 (19) 0.0205 (19) 0.0228 (19) 0.0067 (15) 0.0096 (15) 0.0090 (15)
C5 0.029 (2) 0.023 (2) 0.028 (2) 0.0122 (16) 0.0087 (17) 0.0129 (16)
C6 0.0219 (19) 0.025 (2) 0.028 (2) 0.0079 (15) 0.0019 (16) 0.0074 (16)
C7 0.0189 (17) 0.021 (2) 0.033 (2) 0.0059 (14) 0.0093 (16) 0.0069 (16)
C8 0.0171 (16) 0.0173 (18) 0.0192 (17) 0.0078 (13) 0.0024 (14) 0.0069 (14)
C9 0.0236 (18) 0.0152 (18) 0.0247 (19) 0.0069 (14) 0.0022 (15) 0.0067 (15)
C10 0.0232 (18) 0.0152 (18) 0.0210 (18) 0.0064 (14) 0.0006 (15) 0.0086 (14)
C11 0.031 (2) 0.0130 (18) 0.033 (2) 0.0006 (15) 0.0061 (17) 0.0077 (16)
C12 0.0201 (17) 0.0182 (18) 0.0227 (19) 0.0066 (14) 0.0018 (15) 0.0089 (15)
C13 0.0257 (19) 0.022 (2) 0.025 (2) 0.0067 (15) 0.0031 (16) 0.0066 (16)
C14 0.028 (2) 0.031 (2) 0.023 (2) 0.0126 (16) 0.0058 (16) 0.0069 (17)
C15 0.0226 (19) 0.037 (2) 0.029 (2) 0.0038 (16) 0.0067 (16) 0.0126 (18)
C16 0.027 (2) 0.027 (2) 0.028 (2) 0.0010 (16) 0.0059 (17) 0.0098 (17)
C17 0.0214 (18) 0.0199 (19) 0.0227 (19) 0.0075 (14) 0.0029 (15) 0.0084 (15)
C18 0.0256 (19) 0.0168 (18) 0.0243 (19) 0.0055 (14) 0.0047 (15) 0.0073 (15)
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Geometric parameters (Å, °)

S1—C8 1.750 (4) C6—H6 0.9500
S1—C7 1.818 (4) C7—H7A 0.9900
S2—C8 1.673 (4) C7—H7B 0.9900
N1—C8 1.332 (5) C9—C10 1.442 (5)
N1—N2 1.382 (4) C9—H9 0.9500
N1—H1 0.8800 C10—C18 1.380 (5)
N2—C9 1.284 (5) C11—H11A 0.9800
N3—C12 1.371 (5) C11—H11B 0.9800
N3—C10 1.386 (5) C11—H11C 0.9800
N3—C11 1.460 (5) C12—C17 1.409 (5)
C1—C2 1.377 (5) C12—C13 1.409 (5)
C1—C6 1.395 (5) C13—C14 1.374 (6)
C1—C7 1.509 (5) C13—H13 0.9500
C2—C3 1.392 (5) C14—C15 1.401 (6)
C2—H2 0.9500 C14—H14 0.9500
C3—C4 1.387 (5) C15—C16 1.377 (6)
C3—H3 0.9500 C15—H15 0.9500
C4—C5 1.380 (6) C16—C17 1.405 (6)
C4—H4 0.9500 C16—H16 0.9500
C5—C6 1.388 (6) C17—C18 1.415 (5)
C5—H5 0.9500 C18—H18 0.9500
C8—S1—C7 101.41 (18) S2—C8—S1 124.0 (2)
C8—N1—N2 120.4 (3) N2—C9—C10 124.5 (3)
C8—N1—H1 119.8 N2—C9—H9 117.7
N2—N1—H1 119.8 C10—C9—H9 117.7
C9—N2—N1 114.0 (3) C18—C10—N3 109.2 (3)
C12—N3—C10 107.9 (3) C18—C10—C9 123.9 (3)
C12—N3—C11 123.7 (3) N3—C10—C9 126.9 (3)
C10—N3—C11 128.4 (3) N3—C11—H11A 109.5
C2—C1—C6 118.9 (3) N3—C11—H11B 109.5
C2—C1—C7 121.4 (3) H11A—C11—H11B 109.5
C6—C1—C7 119.7 (4) N3—C11—H11C 109.5
C1—C2—C3 121.1 (3) H11A—C11—H11C 109.5
C1—C2—H2 119.5 H11B—C11—H11C 109.5
C3—C2—H2 119.5 N3—C12—C17 108.9 (3)
C4—C3—C2 119.5 (4) N3—C12—C13 129.3 (4)
C4—C3—H3 120.2 C17—C12—C13 121.8 (4)
C2—C3—H3 120.2 C14—C13—C12 117.2 (4)
C5—C4—C3 119.9 (4) C14—C13—H13 121.4
C5—C4—H4 120.1 C12—C13—H13 121.4
C3—C4—H4 120.1 C13—C14—C15 121.8 (4)
C4—C5—C6 120.2 (4) C13—C14—H14 119.1
C4—C5—H5 119.9 C15—C14—H14 119.1
C6—C5—H5 119.9 C16—C15—C14 121.2 (4)
C5—C6—C1 120.3 (4) C16—C15—H15 119.4
C5—C6—H6 119.8 C14—C15—H15 119.4
C1—C6—H6 119.8 C15—C16—C17 118.8 (4)
C1—C7—S1 108.2 (3) C15—C16—H16 120.6
C1—C7—H7A 110.0 C17—C16—H16 120.6
S1—C7—H7A 110.0 C16—C17—C12 119.3 (4)
C1—C7—H7B 110.0 C16—C17—C18 134.3 (4)
S1—C7—H7B 110.0 C12—C17—C18 106.4 (3)
H7A—C7—H7B 108.4 C10—C18—C17 107.5 (3)
N1—C8—S2 121.5 (3) C10—C18—H18 126.2
N1—C8—S1 114.4 (3) C17—C18—H18 126.2
C8—N1—N2—C9 179.1 (3) N2—C9—C10—C18 −177.4 (4)
C6—C1—C2—C3 −0.9 (6) N2—C9—C10—N3 0.5 (6)
C7—C1—C2—C3 177.7 (4) C10—N3—C12—C17 −0.2 (4)
C1—C2—C3—C4 0.2 (6) C11—N3—C12—C17 179.8 (3)
C2—C3—C4—C5 0.7 (6) C10—N3—C12—C13 179.8 (4)
C3—C4—C5—C6 −0.8 (6) C11—N3—C12—C13 −0.2 (6)
C4—C5—C6—C1 0.0 (6) N3—C12—C13—C14 179.4 (4)
C2—C1—C6—C5 0.8 (6) C17—C12—C13—C14 −0.6 (6)
C7—C1—C6—C5 −177.8 (4) C12—C13—C14—C15 0.3 (6)
C2—C1—C7—S1 102.5 (4) C13—C14—C15—C16 0.2 (7)
C6—C1—C7—S1 −78.9 (4) C14—C15—C16—C17 −0.3 (6)
C8—S1—C7—C1 172.9 (3) C15—C16—C17—C12 0.0 (6)
N2—N1—C8—S2 178.8 (2) C15—C16—C17—C18 −179.5 (4)
N2—N1—C8—S1 −2.4 (4) N3—C12—C17—C16 −179.5 (3)
C7—S1—C8—N1 −179.1 (3) C13—C12—C17—C16 0.5 (6)
C7—S1—C8—S2 −0.3 (3) N3—C12—C17—C18 0.1 (4)
N1—N2—C9—C10 178.4 (3) C13—C12—C17—C18 −179.9 (3)
C12—N3—C10—C18 0.2 (4) N3—C10—C18—C17 −0.2 (4)
C11—N3—C10—C18 −179.8 (4) C9—C10—C18—C17 178.1 (3)
C12—N3—C10—C9 −177.9 (3) C16—C17—C18—C10 179.5 (4)
C11—N3—C10—C9 2.0 (6) C12—C17—C18—C10 0.0 (4)
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Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N1—H1···S2i 0.88 2.49 3.336 (3) 161
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Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2848).

References

  1. Ali, M. A., Mirza, A. H., Hamid, M. H. S. A., Bujang, F. H. & Bernhardt, P. V. (2004). Polyhedron, 23, 2405–2412.
  2. Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  3. Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  4. Chan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628–o629.
  5. Fun, H.-K., Sivakumar, K., Yip, B.-C., Tian, Y.-P., Duan, C.-Y., Lu, Z.-L. & You, X.-Z. (1995). Acta Cryst. C51, 2080–2083.
  6. How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023–o3024.
  7. Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441–o2443.
  8. Qiu, X.-Y. & Luo, Z.-G. (2007). Acta Cryst. E63, o4339.
  9. Roy, S., Mandal, T. N., Barik, A., Pal, S., Gupta, S., Hazra, A., Butcher, R. J., Hunter, A. D., Zeller, M. & Kar, S. K. (2007). Polyhedron, 26, 2603–2611.
  10. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  11. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  12. Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2691–2699.
  13. Westrip, S. P. (2008). publCIF In preparation.
  14. Xu, Z., Alyea, E. C., Ferguson, G. & Jennings, M. C. (1991). Polyhedron, 10, 1625–1629.
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  16. Zhang, M.-L., Tian, Y.-P., Zhang, X.-J., Wu, J.-Y., Zhang, S.-Y., Wang, D., Jiang, M.-H., Chantrapromma, S. & Fun, H.-K. (2004). Transition Met. Chem.29, 596–602.

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/S1600536808038579/hb2848sup1.cif

e-64-o2430-sup1.cif (17.5KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038579/hb2848Isup2.hkl

e-64-o2430-Isup2.hkl (182.9KB, 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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