organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 November 2008; accepted 19 November 2008; online 26 November 2008)

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[Ali, M. A., Mirza, A. H., Hamid, M. H. S. A., Bujang, F. H. & Bernhardt, P. V. (2004). Polyhedron, 23, 2405-2412.]); Chan et al. (2003[Chan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628-o629.]); Fun et al. (1995[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.]); How et al. (2007[How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023-o3024.]); Khoo et al. (2005[Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.]); Qiu & Luo (2007[Qiu, X.-Y. & Luo, Z.-G. (2007). Acta Cryst. E63, o4339.]); Roy et al. (2007[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.]); Tarafder et al. (2002[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2691-2699.]); Xu et al. (1991[Xu, Z., Alyea, E. C., Ferguson, G. & Jennings, M. C. (1991). Polyhedron, 10, 1625-1629.], 2002[Xu, L., Zhou, J.-H., Chen, X.-T. & You, X.-Z. (2002). Acta Cryst. C58, o513-o514.]); Zhang et al. (2004[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.]).

[Scheme 1]

Experimental

Crystal data
  • C18H17N3S2

  • Mr = 339.47

  • Triclinic, [P \overline 1]

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.880, Tmax = 0.987

  • 7605 measured reflections

  • 3732 independent reflections

  • 2653 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.075

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯S2i 0.88 2.49 3.336 (3) 161
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: pubCIF (Westrip, 2008[Westrip, S. P. (2008). publCIF. In preparation.]).

Supporting information


Comment top

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).

Related literature top

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).

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top
[Figure 1] Fig. 1. The molecular structue of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Benzyl N'-(1-methyl-1H-indol-2-ylmethylene)hydrazinecarbodithioate top
Crystal data top
C18H17N3S2Z = 2
Mr = 339.47F(000) = 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 = 2.6–28.1°
c = 14.1936 (4) ŵ = 0.33 mm1
α = 108.203 (2)°T = 100 K
β = 90.230 (2)°Prism, orange
γ = 96.191 (2)°0.40 × 0.08 × 0.04 mm
V = 818.70 (3) Å3
Data collection top
Bruker SMART APEX
diffractometer
3732 independent reflections
Radiation source: fine-focus sealed tube2653 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 27.5°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.880, Tmax = 0.987k = 1515
7605 measured reflectionsl = 1818
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.225H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.1301P)2 + 0.2413P]
where P = (Fo2 + 2Fc2)/3
3732 reflections(Δ/σ)max = 0.001
209 parametersΔρmax = 1.56 e Å3
0 restraintsΔρmin = 0.59 e Å3
Crystal data top
C18H17N3S2γ = 96.191 (2)°
Mr = 339.47V = 818.70 (3) Å3
Triclinic, P1Z = 2
a = 5.1203 (1) ÅMo Kα radiation
b = 11.9377 (3) ŵ = 0.33 mm1
c = 14.1936 (4) ÅT = 100 K
α = 108.203 (2)°0.40 × 0.08 × 0.04 mm
β = 90.230 (2)°
Data collection top
Bruker SMART APEX
diffractometer
3732 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2653 reflections with I > 2σ(I)
Tmin = 0.880, Tmax = 0.987Rint = 0.047
7605 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0750 restraints
wR(F2) = 0.225H-atom parameters constrained
S = 1.13Δρmax = 1.56 e Å3
3732 reflectionsΔρmin = 0.59 e Å3
209 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
N30.1582 (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)
H90.00980.54170.65570.025*
C100.1597 (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*
H11B0.09490.92840.86430.038*
H11C0.13970.85360.81630.038*
C120.3503 (7)0.7444 (3)0.9212 (3)0.0194 (8)
C130.4243 (8)0.8289 (4)1.0078 (3)0.0240 (8)
H130.33710.90751.03040.029*
C140.6278 (8)0.7930 (4)1.0584 (3)0.0268 (9)
H140.68250.84821.11700.032*
C150.7569 (8)0.6772 (4)1.0260 (3)0.0289 (9)
H150.89720.65561.06280.035*
C160.6840 (8)0.5941 (4)0.9418 (3)0.0273 (9)
H160.77200.51570.92060.033*
C170.4769 (7)0.6274 (3)0.8878 (3)0.0206 (8)
C180.3533 (7)0.5682 (3)0.8002 (3)0.0218 (8)
H180.39580.48770.76050.026*
Atomic displacement parameters (Å2) top
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, º) top
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—C18177.4 (4)
C6—C1—C2—C30.9 (6)N2—C9—C10—N30.5 (6)
C7—C1—C2—C3177.7 (4)C10—N3—C12—C170.2 (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—C60.8 (6)C11—N3—C12—C130.2 (6)
C4—C5—C6—C10.0 (6)N3—C12—C13—C14179.4 (4)
C2—C1—C6—C50.8 (6)C17—C12—C13—C140.6 (6)
C7—C1—C6—C5177.8 (4)C12—C13—C14—C150.3 (6)
C2—C1—C7—S1102.5 (4)C13—C14—C15—C160.2 (7)
C6—C1—C7—S178.9 (4)C14—C15—C16—C170.3 (6)
C8—S1—C7—C1172.9 (3)C15—C16—C17—C120.0 (6)
N2—N1—C8—S2178.8 (2)C15—C16—C17—C18179.5 (4)
N2—N1—C8—S12.4 (4)N3—C12—C17—C16179.5 (3)
C7—S1—C8—N1179.1 (3)C13—C12—C17—C160.5 (6)
C7—S1—C8—S20.3 (3)N3—C12—C17—C180.1 (4)
N1—N2—C9—C10178.4 (3)C13—C12—C17—C18179.9 (3)
C12—N3—C10—C180.2 (4)N3—C10—C18—C170.2 (4)
C11—N3—C10—C18179.8 (4)C9—C10—C18—C17178.1 (3)
C12—N3—C10—C9177.9 (3)C16—C17—C18—C10179.5 (4)
C11—N3—C10—C92.0 (6)C12—C17—C18—C100.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S2i0.882.493.336 (3)161
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC18H17N3S2
Mr339.47
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)5.1203 (1), 11.9377 (3), 14.1936 (4)
α, β, γ (°)108.203 (2), 90.230 (2), 96.191 (2)
V3)818.70 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.33
Crystal size (mm)0.40 × 0.08 × 0.04
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.880, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
7605, 3732, 2653
Rint0.047
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.075, 0.225, 1.13
No. of reflections3732
No. of parameters209
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.56, 0.59

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), pubCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···S2i0.882.493.336 (3)161
Symmetry code: (i) x+1, y+1, z+1.
 

Acknowledgements

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

References

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