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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2430.
Published online 2008 November 26. doi:  10.1107/S1600536808038579
PMCID: PMC2960023

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

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 [triangle]); Chan et al. (2003 [triangle]); Fun et al. (1995 [triangle]); How et al. (2007 [triangle]); Khoo et al. (2005 [triangle]); Qiu & Luo (2007 [triangle]); Roy et al. (2007 [triangle]); Tarafder et al. (2002 [triangle]); Xu et al. (1991 [triangle], 2002 [triangle]); Zhang et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2430-scheme1.jpg

Experimental

Crystal data

  • C18H17N3S2
  • M r = 339.47
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2430-efi1.jpg
  • 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 [triangle]) 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 [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: pubCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Crystal data

C18H17N3S2Z = 2
Mr = 339.47F000 = 356
Triclinic, P1Dx = 1.377 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 5.1203 (1) ÅCell parameters from 2060 reflections
b = 11.9377 (3) Åθ = 2.6–28.1º
c = 14.1936 (4) ŵ = 0.33 mm1
α = 108.203 (2)ºT = 100 (2) K
β = 90.230 (2)ºPrism, orange
γ = 96.191 (2)º0.40 × 0.08 × 0.04 mm
V = 818.70 (3) Å3

Data collection

Bruker SMART APEX diffractometer3732 independent reflections
Radiation source: fine-focus sealed tube2653 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.047
T = 100(2) Kθmax = 27.5º
ω scansθmin = 1.5º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)h = −6→6
Tmin = 0.880, Tmax = 0.987k = −15→15
7605 measured reflectionsl = −18→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.075H-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 reflectionsΔρmax = 1.56 e Å3
209 parametersΔρmin = −0.59 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

xyzUiso*/Ueq
S10.58962 (17)0.85808 (8)0.65532 (7)0.0205 (3)
S20.72855 (18)0.65218 (8)0.48348 (7)0.0221 (3)
N10.3474 (6)0.6436 (3)0.6054 (2)0.0201 (7)
H10.30890.56870.56970.024*
N20.2021 (6)0.6924 (3)0.6868 (2)0.0195 (7)
N3−0.1582 (6)0.7565 (3)0.8569 (2)0.0184 (7)
C10.9083 (7)1.0499 (3)0.6464 (3)0.0215 (8)
C21.1083 (7)1.1026 (3)0.7164 (3)0.0220 (8)
H21.21811.05430.73670.026*
C31.1524 (7)1.2255 (4)0.7581 (3)0.0225 (8)
H31.29141.26080.80620.027*
C40.9918 (7)1.2961 (3)0.7288 (3)0.0220 (8)
H41.02181.38010.75630.026*
C50.7885 (8)1.2441 (4)0.6596 (3)0.0245 (8)
H50.67721.29240.64020.029*
C60.7460 (7)1.1216 (4)0.6183 (3)0.0245 (8)
H60.60581.08640.57070.029*
C70.8657 (7)0.9171 (3)0.5981 (3)0.0241 (8)
H7A1.02570.88140.60750.029*
H7B0.82780.89780.52600.029*
C80.5454 (7)0.7094 (3)0.5804 (3)0.0172 (7)
C90.0151 (7)0.6197 (3)0.7016 (3)0.0207 (8)
H9−0.00980.54170.65570.025*
C10−0.1597 (7)0.6484 (3)0.7829 (3)0.0188 (8)
C110.0120 (8)0.8667 (3)0.8688 (3)0.0256 (9)
H11A0.10530.89220.93370.038*
H11B−0.09490.92840.86430.038*
H11C0.13970.85360.81630.038*
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)
H13−0.33710.90751.03040.029*
C14−0.6278 (8)0.7930 (4)1.0584 (3)0.0268 (9)
H14−0.68250.84821.11700.032*
C15−0.7569 (8)0.6772 (4)1.0260 (3)0.0289 (9)
H15−0.89720.65561.06280.035*
C16−0.6840 (8)0.5941 (4)0.9418 (3)0.0273 (9)
H16−0.77200.51570.92060.033*
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)
H18−0.39580.48770.76050.026*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0212 (5)0.0153 (5)0.0253 (5)0.0064 (3)0.0069 (4)0.0053 (4)
S20.0263 (5)0.0180 (5)0.0230 (5)0.0078 (4)0.0098 (4)0.0060 (4)
N10.0221 (15)0.0163 (15)0.0211 (16)0.0058 (12)0.0055 (13)0.0034 (12)
N20.0221 (15)0.0181 (16)0.0211 (16)0.0090 (12)0.0056 (13)0.0081 (13)
N30.0220 (15)0.0131 (15)0.0230 (16)0.0065 (12)0.0057 (13)0.0081 (12)
C10.0207 (18)0.0182 (19)0.027 (2)0.0074 (14)0.0118 (15)0.0076 (15)
C20.0193 (18)0.0203 (19)0.030 (2)0.0093 (14)0.0061 (15)0.0101 (16)
C30.0194 (18)0.023 (2)0.025 (2)0.0051 (14)0.0031 (15)0.0075 (16)
C40.0253 (19)0.0205 (19)0.0228 (19)0.0067 (15)0.0096 (15)0.0090 (15)
C50.029 (2)0.023 (2)0.028 (2)0.0122 (16)0.0087 (17)0.0129 (16)
C60.0219 (19)0.025 (2)0.028 (2)0.0079 (15)0.0019 (16)0.0074 (16)
C70.0189 (17)0.021 (2)0.033 (2)0.0059 (14)0.0093 (16)0.0069 (16)
C80.0171 (16)0.0173 (18)0.0192 (17)0.0078 (13)0.0024 (14)0.0069 (14)
C90.0236 (18)0.0152 (18)0.0247 (19)0.0069 (14)0.0022 (15)0.0067 (15)
C100.0232 (18)0.0152 (18)0.0210 (18)0.0064 (14)0.0006 (15)0.0086 (14)
C110.031 (2)0.0130 (18)0.033 (2)0.0006 (15)0.0061 (17)0.0077 (16)
C120.0201 (17)0.0182 (18)0.0227 (19)0.0066 (14)0.0018 (15)0.0089 (15)
C130.0257 (19)0.022 (2)0.025 (2)0.0067 (15)0.0031 (16)0.0066 (16)
C140.028 (2)0.031 (2)0.023 (2)0.0126 (16)0.0058 (16)0.0069 (17)
C150.0226 (19)0.037 (2)0.029 (2)0.0038 (16)0.0067 (16)0.0126 (18)
C160.027 (2)0.027 (2)0.028 (2)0.0010 (16)0.0059 (17)0.0098 (17)
C170.0214 (18)0.0199 (19)0.0227 (19)0.0075 (14)0.0029 (15)0.0084 (15)
C180.0256 (19)0.0168 (18)0.0243 (19)0.0055 (14)0.0047 (15)0.0073 (15)

Geometric parameters (Å, °)

S1—C81.750 (4)C6—H60.9500
S1—C71.818 (4)C7—H7A0.9900
S2—C81.673 (4)C7—H7B0.9900
N1—C81.332 (5)C9—C101.442 (5)
N1—N21.382 (4)C9—H90.9500
N1—H10.8800C10—C181.380 (5)
N2—C91.284 (5)C11—H11A0.9800
N3—C121.371 (5)C11—H11B0.9800
N3—C101.386 (5)C11—H11C0.9800
N3—C111.460 (5)C12—C171.409 (5)
C1—C21.377 (5)C12—C131.409 (5)
C1—C61.395 (5)C13—C141.374 (6)
C1—C71.509 (5)C13—H130.9500
C2—C31.392 (5)C14—C151.401 (6)
C2—H20.9500C14—H140.9500
C3—C41.387 (5)C15—C161.377 (6)
C3—H30.9500C15—H150.9500
C4—C51.380 (6)C16—C171.405 (6)
C4—H40.9500C16—H160.9500
C5—C61.388 (6)C17—C181.415 (5)
C5—H50.9500C18—H180.9500
C8—S1—C7101.41 (18)S2—C8—S1124.0 (2)
C8—N1—N2120.4 (3)N2—C9—C10124.5 (3)
C8—N1—H1119.8N2—C9—H9117.7
N2—N1—H1119.8C10—C9—H9117.7
C9—N2—N1114.0 (3)C18—C10—N3109.2 (3)
C12—N3—C10107.9 (3)C18—C10—C9123.9 (3)
C12—N3—C11123.7 (3)N3—C10—C9126.9 (3)
C10—N3—C11128.4 (3)N3—C11—H11A109.5
C2—C1—C6118.9 (3)N3—C11—H11B109.5
C2—C1—C7121.4 (3)H11A—C11—H11B109.5
C6—C1—C7119.7 (4)N3—C11—H11C109.5
C1—C2—C3121.1 (3)H11A—C11—H11C109.5
C1—C2—H2119.5H11B—C11—H11C109.5
C3—C2—H2119.5N3—C12—C17108.9 (3)
C4—C3—C2119.5 (4)N3—C12—C13129.3 (4)
C4—C3—H3120.2C17—C12—C13121.8 (4)
C2—C3—H3120.2C14—C13—C12117.2 (4)
C5—C4—C3119.9 (4)C14—C13—H13121.4
C5—C4—H4120.1C12—C13—H13121.4
C3—C4—H4120.1C13—C14—C15121.8 (4)
C4—C5—C6120.2 (4)C13—C14—H14119.1
C4—C5—H5119.9C15—C14—H14119.1
C6—C5—H5119.9C16—C15—C14121.2 (4)
C5—C6—C1120.3 (4)C16—C15—H15119.4
C5—C6—H6119.8C14—C15—H15119.4
C1—C6—H6119.8C15—C16—C17118.8 (4)
C1—C7—S1108.2 (3)C15—C16—H16120.6
C1—C7—H7A110.0C17—C16—H16120.6
S1—C7—H7A110.0C16—C17—C12119.3 (4)
C1—C7—H7B110.0C16—C17—C18134.3 (4)
S1—C7—H7B110.0C12—C17—C18106.4 (3)
H7A—C7—H7B108.4C10—C18—C17107.5 (3)
N1—C8—S2121.5 (3)C10—C18—H18126.2
N1—C8—S1114.4 (3)C17—C18—H18126.2
C8—N1—N2—C9179.1 (3)N2—C9—C10—C18−177.4 (4)
C6—C1—C2—C3−0.9 (6)N2—C9—C10—N30.5 (6)
C7—C1—C2—C3177.7 (4)C10—N3—C12—C17−0.2 (4)
C1—C2—C3—C40.2 (6)C11—N3—C12—C17179.8 (3)
C2—C3—C4—C50.7 (6)C10—N3—C12—C13179.8 (4)
C3—C4—C5—C6−0.8 (6)C11—N3—C12—C13−0.2 (6)
C4—C5—C6—C10.0 (6)N3—C12—C13—C14179.4 (4)
C2—C1—C6—C50.8 (6)C17—C12—C13—C14−0.6 (6)
C7—C1—C6—C5−177.8 (4)C12—C13—C14—C150.3 (6)
C2—C1—C7—S1102.5 (4)C13—C14—C15—C160.2 (7)
C6—C1—C7—S1−78.9 (4)C14—C15—C16—C17−0.3 (6)
C8—S1—C7—C1172.9 (3)C15—C16—C17—C120.0 (6)
N2—N1—C8—S2178.8 (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—C160.5 (6)
C7—S1—C8—S2−0.3 (3)N3—C12—C17—C180.1 (4)
N1—N2—C9—C10178.4 (3)C13—C12—C17—C18−179.9 (3)
C12—N3—C10—C180.2 (4)N3—C10—C18—C17−0.2 (4)
C11—N3—C10—C18−179.8 (4)C9—C10—C18—C17178.1 (3)
C12—N3—C10—C9−177.9 (3)C16—C17—C18—C10179.5 (4)
C11—N3—C10—C92.0 (6)C12—C17—C18—C100.0 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···S2i0.882.493.336 (3)161

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

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