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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Oct 11;64(Pt 11):o2107. doi: 10.1107/S160053680803198X

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

Hamid Khaledi a, Hapipah Mohd Ali a, Seik Weng Ng a,*
PMCID: PMC2959648  PMID: 21580971

Abstract

The C10H8N3S2 portion of the title mol­ecule, C17H15N3S3, is nearly planar (r.m.s. deviation 0.05 Å); this unit and the phenyl ring subtend an angle of 114.5 (2)° at the methyl­ene C atom.

Related literature

For other Schiff bases derived by condensing S-benzyl hydrazinecarbodithio­ate with either aromatic aldehydes or ketones, see: Ali et al. (2004 ▶); Chan et al. (2003 ▶); Fun et al. (1995 ▶); How et al. (2007a ▶,b ▶,c ▶); Khoo et al. (2005 ▶); Qiu & Luo (2007 ▶); Roy et al. (2007 ▶); Tarafder et al. (2002 ▶); Xu et al. (1991 ▶); Zhang et al. (2004 ▶).graphic file with name e-64-o2107-scheme1.jpg

Experimental

Crystal data

  • C17H15N3S2

  • M r = 325.44

  • Monoclinic, Inline graphic

  • a = 15.4936 (7) Å

  • b = 9.8114 (4) Å

  • c = 10.2531 (4) Å

  • β = 98.432 (3)°

  • V = 1541.8 (1) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 100 (2) K

  • 0.25 × 0.10 × 0.03 mm

Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.919, T max = 0.990

  • 8531 measured reflections

  • 3383 independent reflections

  • 2323 reflections with I > 2σ(I)

  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049

  • wR(F 2) = 0.118

  • S = 1.01

  • 3383 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; 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: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803198X/tk2309sup1.cif

e-64-o2107-sup1.cif (16.7KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803198X/tk2309Isup2.hkl

e-64-o2107-Isup2.hkl (165.9KB, hkl)

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

Acknowledgments

The authors thank the University of Malaya for funding this study (Science Fund Grants 12-02-03-2031 and 12-02-03-2051).

supplementary crystallographic information

Comment

The structure of (I), Fig. 1, shows bond distances for N1—N2 and N2—C9 of 1.382 (3) and 1.287 (3) Å, respectively, confirming the assignment shown in the Scheme. The molecule is bent about the methylene-C7 atom so that the residues on either side are approximately orthogonal. The amino groups do not form any hydrogen bonds.

Experimental

Indole-3-carbaldehyde (0.37 g, 2.5 mmol) and S-benzyl dithiocarbazate (0.50 g, 2.5 mmol) were heated in methanol (40 ml) for 3 h. The solution was set aside for the formation of yellow crystals.

Refinement

Hydrogen atoms were placed at calculated positions (C—H 0.95–0.99, N—H 0.88 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2 times Ueq(C,N).

Figures

Fig. 1.

Fig. 1.

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Thermal ellipsoid plot (Barbour, 2001) of C17H15N2S3 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C17H15N3S2 F(000) = 680
Mr = 325.44 Dx = 1.402 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 1305 reflections
a = 15.4936 (7) Å θ = 2.5–23.2°
b = 9.8114 (4) Å µ = 0.34 mm−1
c = 10.2531 (4) Å T = 100 K
β = 98.432 (3)° Prism, light yellow
V = 1541.8 (1) Å3 0.25 × 0.10 × 0.03 mm
Z = 4
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Data collection

Bruker SMART APEX diffractometer 3383 independent reflections
Radiation source: fine-focus sealed tube 2323 reflections with I > 2σ(I)
graphite Rint = 0.058
ω scans θmax = 27°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −20→20
Tmin = 0.919, Tmax = 0.990 k = −12→12
8531 measured reflections l = −13→8
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118 H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0391P)2 + 1.1115P] where P = (Fo2 + 2Fc2)/3
3383 reflections (Δ/σ)max = 0.001
199 parameters Δρmax = 0.48 e Å−3
0 restraints Δρmin = −0.33 e Å−3
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
S1 0.75015 (5) 0.74458 (7) 0.47255 (7) 0.02090 (18)
S2 0.87340 (5) 0.53986 (7) 0.36891 (7) 0.02198 (19)
N1 0.70350 (15) 0.5227 (2) 0.3457 (2) 0.0217 (5)
H1 0.7086 0.4440 0.3063 0.026*
N2 0.62145 (15) 0.5704 (2) 0.3596 (2) 0.0212 (5)
N3 0.32371 (16) 0.5105 (2) 0.2983 (2) 0.0253 (6)
H3 0.2706 0.4795 0.2732 0.030*
C1 0.87962 (17) 0.9360 (3) 0.4432 (3) 0.0188 (6)
C2 0.89308 (18) 0.9185 (3) 0.3115 (3) 0.0216 (6)
H2 0.8855 0.8312 0.2714 0.026*
C3 0.91737 (18) 1.0283 (3) 0.2403 (3) 0.0242 (7)
H3a 0.9272 1.0156 0.1518 0.029*
C4 0.92738 (18) 1.1564 (3) 0.2970 (3) 0.0259 (7)
H4 0.9436 1.2316 0.2475 0.031*
C5 0.91353 (19) 1.1742 (3) 0.4261 (3) 0.0245 (7)
H5 0.9202 1.2619 0.4654 0.029*
C6 0.89010 (18) 1.0647 (3) 0.4983 (3) 0.0212 (6)
H6 0.8811 1.0780 0.5871 0.025*
C7 0.85739 (18) 0.8174 (3) 0.5249 (3) 0.0210 (6)
H7A 0.8609 0.8475 0.6176 0.025*
H7B 0.9018 0.7453 0.5220 0.025*
C8 0.77530 (18) 0.5938 (3) 0.3909 (3) 0.0191 (6)
C9 0.55868 (18) 0.4859 (3) 0.3251 (3) 0.0209 (6)
H9 0.5717 0.3976 0.2953 0.025*
C10 0.46972 (19) 0.5221 (3) 0.3305 (3) 0.0204 (6)
C11 0.39833 (19) 0.4445 (3) 0.2826 (3) 0.0230 (6)
H11 0.4009 0.3569 0.2438 0.028*
C12 0.43633 (18) 0.6451 (3) 0.3827 (3) 0.0197 (6)
C13 0.47407 (19) 0.7591 (3) 0.4513 (3) 0.0217 (6)
H13 0.5357 0.7694 0.4680 0.026*
C14 0.42007 (19) 0.8557 (3) 0.4939 (3) 0.0255 (7)
H14 0.4452 0.9328 0.5412 0.031*
C15 0.3294 (2) 0.8434 (3) 0.4694 (3) 0.0285 (7)
H15 0.2941 0.9122 0.4997 0.034*
C16 0.2901 (2) 0.7323 (3) 0.4016 (3) 0.0284 (7)
H16 0.2284 0.7238 0.3842 0.034*
C17 0.34423 (19) 0.6341 (3) 0.3602 (3) 0.0222 (6)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
S1 0.0225 (4) 0.0184 (3) 0.0229 (4) −0.0009 (3) 0.0070 (3) −0.0025 (3)
S2 0.0234 (4) 0.0212 (4) 0.0226 (4) 0.0034 (3) 0.0075 (3) 0.0014 (3)
N1 0.0231 (13) 0.0194 (12) 0.0234 (14) −0.0005 (10) 0.0060 (11) −0.0047 (10)
N2 0.0197 (12) 0.0236 (13) 0.0211 (14) −0.0023 (10) 0.0062 (10) 0.0016 (11)
N3 0.0220 (13) 0.0285 (14) 0.0249 (14) −0.0048 (11) 0.0022 (11) 0.0006 (11)
C1 0.0166 (14) 0.0203 (14) 0.0195 (16) −0.0007 (11) 0.0027 (12) 0.0006 (12)
C2 0.0223 (15) 0.0239 (15) 0.0181 (16) −0.0013 (12) 0.0012 (12) −0.0037 (12)
C3 0.0235 (15) 0.0337 (17) 0.0158 (15) 0.0008 (13) 0.0038 (12) 0.0034 (13)
C4 0.0236 (15) 0.0250 (15) 0.0295 (19) −0.0006 (13) 0.0045 (13) 0.0106 (14)
C5 0.0262 (16) 0.0198 (15) 0.0277 (18) 0.0005 (12) 0.0041 (13) −0.0016 (13)
C6 0.0228 (15) 0.0218 (15) 0.0196 (16) 0.0036 (12) 0.0050 (12) −0.0002 (12)
C7 0.0227 (15) 0.0209 (15) 0.0196 (16) −0.0006 (12) 0.0032 (12) −0.0010 (12)
C8 0.0265 (15) 0.0170 (14) 0.0149 (15) 0.0008 (11) 0.0064 (12) 0.0024 (11)
C9 0.0277 (16) 0.0217 (15) 0.0142 (15) −0.0022 (12) 0.0058 (12) −0.0003 (12)
C10 0.0268 (15) 0.0201 (14) 0.0140 (15) −0.0048 (12) 0.0020 (12) 0.0024 (12)
C11 0.0297 (16) 0.0217 (15) 0.0180 (16) −0.0046 (13) 0.0054 (13) 0.0009 (13)
C12 0.0233 (15) 0.0220 (15) 0.0143 (15) −0.0039 (12) 0.0044 (12) 0.0040 (12)
C13 0.0227 (15) 0.0248 (15) 0.0177 (16) −0.0043 (12) 0.0037 (12) 0.0041 (13)
C14 0.0315 (17) 0.0253 (16) 0.0205 (17) −0.0039 (13) 0.0063 (13) −0.0028 (13)
C15 0.0291 (17) 0.0296 (17) 0.0277 (18) 0.0022 (14) 0.0077 (14) −0.0038 (14)
C16 0.0231 (16) 0.0340 (18) 0.0281 (18) −0.0034 (13) 0.0040 (13) 0.0005 (15)
C17 0.0272 (16) 0.0228 (15) 0.0163 (15) −0.0057 (12) 0.0025 (12) 0.0034 (12)
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Geometric parameters (Å, °)

S1—C8 1.771 (3) C5—H5 0.9500
S1—C7 1.816 (3) C6—H6 0.9500
S2—C8 1.656 (3) C7—H7A 0.9900
N1—C8 1.337 (4) C7—H7B 0.9900
N1—N2 1.382 (3) C9—C10 1.432 (4)
N1—H1 0.8800 C9—H9 0.9500
N2—C9 1.287 (3) C10—C11 1.373 (4)
N3—C11 1.355 (4) C10—C12 1.446 (4)
N3—C17 1.384 (4) C11—H11 0.9500
N3—H3 0.8800 C12—C13 1.402 (4)
C1—C6 1.383 (4) C12—C17 1.416 (4)
C1—C2 1.407 (4) C13—C14 1.377 (4)
C1—C7 1.503 (4) C13—H13 0.9500
C2—C3 1.384 (4) C14—C15 1.395 (4)
C2—H2 0.9500 C14—H14 0.9500
C3—C4 1.384 (4) C15—C16 1.385 (4)
C3—H3a 0.9500 C15—H15 0.9500
C4—C5 1.384 (4) C16—C17 1.384 (4)
C4—H4 0.9500 C16—H16 0.9500
C5—C6 1.383 (4)
C8—S1—C7 102.30 (13) H7A—C7—H7B 107.6
C8—N1—N2 121.2 (2) N1—C8—S2 121.3 (2)
C8—N1—H1 119.4 N1—C8—S1 111.7 (2)
N2—N1—H1 119.4 S2—C8—S1 126.97 (17)
C9—N2—N1 115.0 (2) N2—C9—C10 121.5 (3)
C11—N3—C17 109.3 (2) N2—C9—H9 119.3
C11—N3—H3 125.4 C10—C9—H9 119.3
C17—N3—H3 125.4 C11—C10—C9 125.3 (3)
C6—C1—C2 118.6 (3) C11—C10—C12 106.4 (3)
C6—C1—C7 120.1 (3) C9—C10—C12 128.3 (3)
C2—C1—C7 121.2 (3) N3—C11—C10 110.4 (3)
C3—C2—C1 120.1 (3) N3—C11—H11 124.8
C3—C2—H2 119.9 C10—C11—H11 124.8
C1—C2—H2 119.9 C13—C12—C17 118.6 (3)
C4—C3—C2 120.5 (3) C13—C12—C10 134.9 (3)
C4—C3—H3a 119.8 C17—C12—C10 106.4 (2)
C2—C3—H3a 119.8 C14—C13—C12 118.7 (3)
C3—C4—C5 119.5 (3) C14—C13—H13 120.7
C3—C4—H4 120.2 C12—C13—H13 120.7
C5—C4—H4 120.2 C13—C14—C15 121.7 (3)
C4—C5—C6 120.3 (3) C13—C14—H14 119.2
C4—C5—H5 119.9 C15—C14—H14 119.2
C6—C5—H5 119.9 C16—C15—C14 121.0 (3)
C5—C6—C1 121.0 (3) C16—C15—H15 119.5
C5—C6—H6 119.5 C14—C15—H15 119.5
C1—C6—H6 119.5 C17—C16—C15 117.4 (3)
C1—C7—S1 114.5 (2) C17—C16—H16 121.3
C1—C7—H7A 108.6 C15—C16—H16 121.3
S1—C7—H7A 108.6 C16—C17—N3 129.9 (3)
C1—C7—H7B 108.6 C16—C17—C12 122.6 (3)
S1—C7—H7B 108.6 N3—C17—C12 107.4 (2)
C8—N1—N2—C9 −172.7 (3) C9—C10—C11—N3 −177.4 (3)
C6—C1—C2—C3 0.8 (4) C12—C10—C11—N3 1.3 (3)
C7—C1—C2—C3 −177.1 (3) C11—C10—C12—C13 175.2 (3)
C1—C2—C3—C4 −1.0 (4) C9—C10—C12—C13 −6.2 (5)
C2—C3—C4—C5 0.5 (4) C11—C10—C12—C17 −1.0 (3)
C3—C4—C5—C6 0.2 (4) C9—C10—C12—C17 177.7 (3)
C4—C5—C6—C1 −0.3 (4) C17—C12—C13—C14 0.0 (4)
C2—C1—C6—C5 −0.2 (4) C10—C12—C13—C14 −175.8 (3)
C7—C1—C6—C5 177.7 (3) C12—C13—C14—C15 −0.6 (4)
C6—C1—C7—S1 113.9 (3) C13—C14—C15—C16 0.4 (5)
C2—C1—C7—S1 −68.2 (3) C14—C15—C16—C17 0.4 (5)
C8—S1—C7—C1 103.7 (2) C15—C16—C17—N3 175.7 (3)
N2—N1—C8—S2 −177.5 (2) C15—C16—C17—C12 −1.1 (4)
N2—N1—C8—S1 2.6 (3) C11—N3—C17—C16 −176.7 (3)
C7—S1—C8—N1 179.0 (2) C11—N3—C17—C12 0.4 (3)
C7—S1—C8—S2 −0.9 (2) C13—C12—C17—C16 0.9 (4)
N1—N2—C9—C10 −178.3 (2) C10—C12—C17—C16 177.8 (3)
N2—C9—C10—C11 172.6 (3) C13—C12—C17—N3 −176.6 (2)
N2—C9—C10—C12 −5.8 (5) C10—C12—C17—N3 0.3 (3)
C17—N3—C11—C10 −1.1 (3)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2309).

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. (2007a). Acta Cryst. E63, o3023–o3024.
  7. How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007b). Acta Cryst. E63, o3133–o3134.
  8. How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007c). Acta Cryst. E63, o3135–o3136.
  9. Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441–o2443.
  10. Qiu, X.-Y. & Luo, Z.-G. (2007). Acta Cryst. E63, o4339.
  11. Roy, S., Mandal, T. N., Barik, A. K., Pal, S., Gupta, S., Hazra, A., Butcher, R. J., Hunter, A. D., Zeller, M. & Kar, S. K. (2007). Polyhedron, 26, 2603–2611.
  12. Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  13. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  14. Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2691–2698.
  15. Westrip, S. P. (2008). publCIF In preparation.
  16. Xu, Z., Alyea, E., Ferguson, G. & Jennings, M. C. (1991). Polyhedron, 10, 1625–1629.
  17. 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/S160053680803198X/tk2309sup1.cif

e-64-o2107-sup1.cif (16.7KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803198X/tk2309Isup2.hkl

e-64-o2107-Isup2.hkl (165.9KB, 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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