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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2445.
Published online 2008 November 26. doi:  10.1107/S1600536808038609
PMCID: PMC2959809

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

Abstract

In the crystal of the title compound, C17H15N3S2·0.5C2H6O, the mol­ecules are linked by a pair of N—Haliphatic(...)S hydrogen bonds across a center of inversion, forming a dimer. The ethanol solvent mol­ecule, which is statistically disordered about a crystallographic twofold rotation axis, accepts an N—Haromatic(...)O hydrogen bond; the hydr­oxy group of the solvent mol­ecule is not engaged in hydrogen bonding.

Related literature

For references to benzyl esters of hydrazinecarbodithioic acids, see: Khaledi et al. (2008 [triangle]).

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Object name is e-64-o2445-scheme1.jpg

Experimental

Crystal data

  • C17H15N3S2·0.5C2H6O
  • M r = 348.47
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2445-efi1.jpg
  • a = 13.4225 (2) Å
  • b = 15.4088 (2) Å
  • c = 16.8120 (3) Å
  • β = 102.637 (1)°
  • V = 3392.90 (9) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.32 mm−1
  • T = 100 (2) K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.924, T max = 0.954
  • 14302 measured reflections
  • 3897 independent reflections
  • 3332 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.088
  • S = 1.03
  • 3897 reflections
  • 232 parameters
  • 5 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.40 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/S1600536808038609/hb2851sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038609/hb2851Isup2.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 background references, see: Khaledi et al. (2008).

Experimental

Indole-2-carbaldehyde (0.36 g, 2.5 mmol) and S-benzyldithiocarbazate (0.495 g, 2.5 mmol) were heated in ethanol (40 ml) for 3 h. The solution was set aside for the formation of yellow blocks of (I).

Refinement

C-bound hydrogen atoms were placed at calculated positions (C–H = 0.95–0.99 Å) and refined as riding with U(H) = 1.2–1.5 times Ueq(C). The amino and hydroxy H atoms were located in a difference map, and were refined with distance restraints of N–H = 0.88±0.01 and O–H = 0.84+_0.01 Å; their Uiso values were freely refined.

The ethanol molecule is statistically disordered about a two-fold axis: the O–C distance was restrained to 1.45±0.01 Å and the C–C distance to 1.50+_0.01 Å; the displacement factors of the two C atoms were restrained to be equal.

Figures

Fig. 1.
View of (I) at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Only one orientation of the ethanol molecule is shown.

Crystal data

C17H15N3S2·0.5C2H6OF000 = 1464
Mr = 348.47Dx = 1.364 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5259 reflections
a = 13.4225 (2) Åθ = 2.5–28.3º
b = 15.4088 (2) ŵ = 0.32 mm1
c = 16.8120 (3) ÅT = 100 (2) K
β = 102.637 (1)ºBlock, yellow
V = 3392.90 (9) Å30.25 × 0.20 × 0.15 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer3897 independent reflections
Radiation source: fine-focus sealed tube3332 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
T = 100(2) Kθmax = 27.5º
ω scansθmin = 2.0º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −16→17
Tmin = 0.924, Tmax = 0.954k = −19→20
14302 measured reflectionsl = −21→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0411P)2 + 3.3308P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3897 reflectionsΔρmax = 0.35 e Å3
232 parametersΔρmin = −0.40 e Å3
5 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/UeqOcc. (<1)
S10.58648 (3)0.69507 (2)0.36508 (2)0.01972 (10)
S20.56141 (3)0.50160 (2)0.38844 (2)0.02263 (11)
N10.48149 (10)0.62574 (8)0.46106 (8)0.0201 (3)
H1N0.4612 (15)0.5843 (10)0.4893 (11)0.036 (5)*
N20.45977 (10)0.71147 (8)0.47237 (8)0.0200 (3)
N30.39716 (10)0.88130 (8)0.48940 (8)0.0205 (3)
H3N0.4341 (14)0.8771 (13)0.4528 (10)0.039 (6)*
C10.72885 (12)0.71544 (9)0.27832 (9)0.0199 (3)
C20.83286 (12)0.71386 (11)0.31290 (10)0.0254 (3)
H20.86080.66710.34760.031*
C30.89612 (13)0.77961 (12)0.29733 (10)0.0297 (4)
H30.96710.77760.32120.036*
C40.85687 (13)0.84829 (11)0.24721 (10)0.0260 (3)
H40.90040.89370.23720.031*
C50.75366 (13)0.85010 (10)0.21189 (10)0.0242 (3)
H50.72630.89680.17700.029*
C60.68972 (12)0.78405 (9)0.22712 (10)0.0222 (3)
H60.61900.78580.20240.027*
C70.66018 (12)0.64525 (9)0.29845 (10)0.0211 (3)
H7A0.70110.59620.32640.025*
H7B0.61440.62320.24820.025*
C80.53949 (11)0.60480 (9)0.40842 (9)0.0180 (3)
C90.40256 (11)0.72590 (9)0.52304 (9)0.0203 (3)
H90.38110.67940.55240.024*
C100.37149 (11)0.81355 (9)0.53466 (9)0.0197 (3)
C110.31225 (12)0.84426 (9)0.58549 (9)0.0208 (3)
H110.28480.81110.62330.025*
C120.29954 (11)0.93534 (9)0.57094 (9)0.0192 (3)
C130.35401 (11)0.95615 (9)0.51045 (9)0.0197 (3)
C140.35929 (12)1.04048 (10)0.48156 (10)0.0246 (3)
H140.39601.05330.44070.030*
C150.30886 (13)1.10461 (10)0.51477 (10)0.0269 (4)
H150.31161.16280.49670.032*
C160.25378 (13)1.08549 (10)0.57456 (10)0.0259 (3)
H160.21961.13090.59600.031*
C170.24827 (12)1.00197 (10)0.60284 (10)0.0229 (3)
H170.21050.98970.64310.027*
O10.48913 (18)0.92618 (16)0.34417 (14)0.0289 (5)0.50
H1O0.5523 (10)0.922 (3)0.363 (3)0.045 (13)*0.50
C180.4709 (7)1.0002 (6)0.2875 (4)0.0472 (9)0.50
H18A0.39661.00990.26870.057*0.50
H18B0.50161.05330.31570.057*0.50
C190.5162 (7)0.9824 (6)0.2172 (4)0.0472 (9)0.50
H19A0.50441.03200.17980.071*0.50
H19B0.48470.93040.18880.071*0.50
H19C0.58980.97290.23600.071*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0245 (2)0.01412 (17)0.0230 (2)0.00081 (13)0.01047 (15)0.00013 (13)
S20.0342 (2)0.01388 (17)0.0233 (2)−0.00028 (14)0.01385 (17)−0.00209 (14)
N10.0271 (7)0.0148 (6)0.0210 (7)0.0021 (5)0.0108 (5)0.0004 (5)
N20.0225 (6)0.0171 (6)0.0203 (7)0.0026 (5)0.0042 (5)−0.0024 (5)
N30.0223 (6)0.0210 (6)0.0204 (7)0.0009 (5)0.0092 (5)−0.0024 (5)
C10.0255 (8)0.0185 (7)0.0183 (7)−0.0008 (6)0.0104 (6)−0.0024 (5)
C20.0261 (8)0.0299 (8)0.0217 (8)0.0038 (6)0.0082 (7)0.0082 (6)
C30.0207 (8)0.0439 (10)0.0241 (9)−0.0035 (7)0.0045 (7)0.0074 (7)
C40.0293 (9)0.0299 (8)0.0202 (8)−0.0086 (7)0.0087 (7)0.0026 (6)
C50.0316 (9)0.0207 (7)0.0204 (8)−0.0001 (6)0.0062 (7)0.0028 (6)
C60.0229 (8)0.0213 (7)0.0222 (8)−0.0002 (6)0.0044 (6)−0.0009 (6)
C70.0258 (8)0.0179 (7)0.0221 (8)0.0001 (6)0.0110 (6)−0.0025 (6)
C80.0199 (7)0.0170 (6)0.0169 (7)−0.0003 (5)0.0031 (6)0.0001 (5)
C90.0224 (7)0.0199 (7)0.0182 (7)0.0022 (6)0.0038 (6)−0.0003 (6)
C100.0199 (7)0.0209 (7)0.0178 (7)0.0013 (6)0.0028 (6)−0.0012 (6)
C110.0242 (8)0.0206 (7)0.0181 (8)0.0021 (6)0.0057 (6)−0.0003 (6)
C120.0184 (7)0.0217 (7)0.0164 (7)0.0012 (6)0.0014 (6)−0.0025 (6)
C130.0187 (7)0.0209 (7)0.0190 (8)0.0007 (6)0.0032 (6)−0.0043 (6)
C140.0281 (8)0.0227 (7)0.0235 (8)−0.0033 (6)0.0066 (7)−0.0018 (6)
C150.0333 (9)0.0183 (7)0.0270 (9)0.0001 (6)0.0017 (7)−0.0020 (6)
C160.0265 (8)0.0234 (7)0.0262 (9)0.0053 (6)0.0020 (7)−0.0082 (6)
C170.0224 (8)0.0263 (8)0.0203 (8)0.0030 (6)0.0057 (6)−0.0046 (6)
O10.0238 (12)0.0401 (13)0.0217 (12)−0.0033 (10)0.0026 (10)0.0035 (10)
C180.041 (2)0.050 (3)0.0478 (15)0.0096 (19)0.0033 (12)−0.001 (2)
C190.041 (2)0.050 (3)0.0478 (15)0.0096 (19)0.0033 (12)−0.001 (2)

Geometric parameters (Å, °)

S1—C81.7506 (15)C9—C101.439 (2)
S1—C71.8187 (15)C9—H90.9500
S2—C81.6647 (14)C10—C111.372 (2)
N1—C81.3397 (19)C11—C121.428 (2)
N1—N21.3748 (16)C11—H110.9500
N1—H1N0.875 (9)C12—C171.406 (2)
N2—C91.285 (2)C12—C131.413 (2)
N3—C131.3713 (18)C13—C141.394 (2)
N3—C101.3792 (19)C14—C151.383 (2)
N3—H3N0.873 (9)C14—H140.9500
C1—C21.390 (2)C15—C161.403 (2)
C1—C61.392 (2)C15—H150.9500
C1—C71.507 (2)C16—C171.379 (2)
C2—C31.383 (2)C16—H160.9500
C2—H20.9500C17—H170.9500
C3—C41.383 (2)O1—C181.472 (8)
C3—H30.9500O1—H1O0.839 (10)
C4—C51.383 (2)C18—C191.469 (5)
C4—H40.9500C18—H18A0.9900
C5—C61.391 (2)C18—H18B0.9900
C5—H50.9500C19—H19A0.9800
C6—H60.9500C19—H19B0.9800
C7—H7A0.9900C19—H19C0.9800
C7—H7B0.9900
C8—S1—C7102.42 (7)C11—C10—N3109.34 (13)
C8—N1—N2119.62 (12)C11—C10—C9129.24 (14)
C8—N1—H1N118.6 (13)N3—C10—C9121.37 (14)
N2—N1—H1N121.7 (13)C10—C11—C12107.22 (13)
C9—N2—N1115.70 (13)C10—C11—H11126.4
C13—N3—C10108.88 (12)C12—C11—H11126.4
C13—N3—H3N125.6 (14)C17—C12—C13118.83 (14)
C10—N3—H3N125.5 (14)C17—C12—C11134.62 (15)
C2—C1—C6118.72 (14)C13—C12—C11106.55 (13)
C2—C1—C7120.08 (14)N3—C13—C14129.59 (14)
C6—C1—C7121.17 (14)N3—C13—C12108.01 (13)
C3—C2—C1120.66 (15)C14—C13—C12122.40 (14)
C3—C2—H2119.7C15—C14—C13117.29 (15)
C1—C2—H2119.7C15—C14—H14121.4
C4—C3—C2120.53 (15)C13—C14—H14121.4
C4—C3—H3119.7C14—C15—C16121.36 (15)
C2—C3—H3119.7C14—C15—H15119.3
C3—C4—C5119.29 (15)C16—C15—H15119.3
C3—C4—H4120.4C17—C16—C15121.27 (14)
C5—C4—H4120.4C17—C16—H16119.4
C4—C5—C6120.45 (15)C15—C16—H16119.4
C4—C5—H5119.8C16—C17—C12118.83 (15)
C6—C5—H5119.8C16—C17—H17120.6
C5—C6—C1120.35 (15)C12—C17—H17120.6
C5—C6—H6119.8C18—O1—H1O108 (3)
C1—C6—H6119.8C19—C18—O1109.7 (7)
C1—C7—S1106.10 (10)C19—C18—H18A109.7
C1—C7—H7A110.5O1—C18—H18A109.7
S1—C7—H7A110.5C19—C18—H18B109.7
C1—C7—H7B110.5O1—C18—H18B109.7
S1—C7—H7B110.5H18A—C18—H18B108.2
H7A—C7—H7B108.7C18—C19—H19A109.5
N1—C8—S2121.15 (11)C18—C19—H19B109.5
N1—C8—S1113.45 (10)H19A—C19—H19B109.5
S2—C8—S1125.40 (9)C18—C19—H19C109.5
N2—C9—C10119.03 (14)H19A—C19—H19C109.5
N2—C9—H9120.5H19B—C19—H19C109.5
C10—C9—H9120.5
C8—N1—N2—C9179.09 (14)N2—C9—C10—C11−179.23 (16)
C6—C1—C2—C30.6 (2)N2—C9—C10—N33.6 (2)
C7—C1—C2—C3−177.57 (15)N3—C10—C11—C120.47 (17)
C1—C2—C3—C40.2 (3)C9—C10—C11—C12−176.97 (15)
C2—C3—C4—C5−0.8 (3)C10—C11—C12—C17179.98 (17)
C3—C4—C5—C60.6 (2)C10—C11—C12—C13−0.39 (17)
C4—C5—C6—C10.2 (2)C10—N3—C13—C14179.53 (16)
C2—C1—C6—C5−0.8 (2)C10—N3—C13—C120.12 (17)
C7—C1—C6—C5177.36 (14)C17—C12—C13—N3179.86 (13)
C2—C1—C7—S1106.98 (14)C11—C12—C13—N30.16 (16)
C6—C1—C7—S1−71.14 (16)C17—C12—C13—C140.4 (2)
C8—S1—C7—C1−163.14 (11)C11—C12—C13—C14−179.30 (14)
N2—N1—C8—S2−176.00 (11)N3—C13—C14—C15−179.11 (15)
N2—N1—C8—S13.72 (18)C12—C13—C14—C150.2 (2)
C7—S1—C8—N1179.96 (11)C13—C14—C15—C16−0.6 (2)
C7—S1—C8—S2−0.33 (12)C14—C15—C16—C170.3 (3)
N1—N2—C9—C10−176.43 (13)C15—C16—C17—C120.3 (2)
C13—N3—C10—C11−0.38 (17)C13—C12—C17—C16−0.7 (2)
C13—N3—C10—C9177.30 (13)C11—C12—C17—C16178.94 (16)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1n···S2i0.88 (1)2.52 (1)3.350 (1)159 (2)
N3—H3n···O10.87 (1)2.25 (1)3.047 (3)153 (2)

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: HB2851).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008). Acta Cryst. E64, o2430. [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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