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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o919–o920.
Published online 2008 April 26. doi:  10.1107/S1600536808011082
PMCID: PMC2961326

1H-Indole-3-carbaldehyde thio­semi­carbazone

Abstract

The mol­ecules of the title compound, C10H10N4S, are linked by N—Hindole(...)S hydrogen bonds to form a linear hydrogen-bonded chain. There are two independent mol­ecules in the asymmetric unit.

Related literature

For the synthesis and bateriostatic activity of indole-3-carbaldehyde semithio­carbazone, see: Doyle et al. (1956 [triangle]); Fujikawa et al. (1966 [triangle]); Libermann et al. (1953 [triangle]); Weller et al. (1954 [triangle]). For metal complexes of the compound, see: Bhardwaj & Singh (1994 [triangle]); Dalvi et al. (2004 [triangle]); Garg & Tandon (1988 [triangle]); Kanoongo et al. (1988 [triangle], 1990 [triangle]); Kiran et al. (1986 [triangle]); Kumari et al. (1992a [triangle],b [triangle]; 1993a [triangle],b [triangle]); Rodriguez-Argueelles et al. (2005 [triangle]); Saxena & Singh (1994 [triangle]); Saxena et al. (1993 [triangle], 1994 [triangle]); Singh & Singh (1990 [triangle]); Singh et al. (1987 [triangle], 1988 [triangle]); Varshney & Tandon (1989 [triangle]); Varshney et al. (1989 [triangle], 1996 [triangle]).

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Object name is e-64-0o919-scheme1.jpg

Experimental

Crystal data

  • C10H10N4S
  • M r = 218.28
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o919-efi1.jpg
  • a = 7.1893 (1) Å
  • b = 11.1654 (2) Å
  • c = 13.5373 (3) Å
  • α = 68.887 (1)°
  • β = 85.048 (1)°
  • γ = 82.467 (1)°
  • V = 1004.07 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.29 mm−1
  • T = 123 (2) K
  • 0.44 × 0.24 × 0.04 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.857, T max = 0.988
  • 9295 measured reflections
  • 4527 independent reflections
  • 3142 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.161
  • S = 1.10
  • 4527 reflections
  • 303 parameters
  • 8 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.45 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [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: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011082/rz2196sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011082/rz2196Isup2.hkl

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

Acknowledgments

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02-03–2031) for supporting this study.

supplementary crystallographic information

Comment

The bacteriostatic activity of indole-3-carboxaldehyde thiosemicarbazone is known for a long time (Doyle et al., 1956; Fujikawa et al., 1966; Libermann et al., 1953; Weller et al., 1954). The compound yields complexes with main group as well as transition metal ions.

Experimental

Thiosemicarbazide (0.3 g, 3.3 mmol) and indole-3-carboxaldehyde (0.5 g, 3.3 mmol) were refluxed in ethanol (50 ml) for 2 h. The solvent was removed to give the product Schiff base, and crystals were obtained upon recrystallization from ethanol.

Refinement

The carbon-bound H atoms were placed at calculated positions (C–H 0.95 Å), and were included in the refinement in the riding model approximation with U(H) set to 1.2Ueq(C). The amino H atoms were located in a difference Fouier map, and were refined with a distance restraint of N–H 0.88±0.01 Å.

Figures

Fig. 1.
Thermal ellipsoid plot of the two independent molecules of the title compound. Displacement ellipsoids are drawn at the 70% probability level, and H atoms are shown as spheres of arbitrary radii.
Fig. 2.
Chain structure of the title compound. Intermolecular H bonds are shown as dashed lines.

Crystal data

C10H10N4SZ = 4
Mr = 218.28F000 = 456
Triclinic, P1Dx = 1.444 Mg m3
Hall symbol: -P 1Mo Kα radiation λ = 0.71073 Å
a = 7.1893 (1) ÅCell parameters from 4065 reflections
b = 11.1654 (2) Åθ = 3.6–30.8º
c = 13.5373 (3) ŵ = 0.29 mm1
α = 68.887 (1)ºT = 123 (2) K
β = 85.048 (1)ºWedge, colorless
γ = 82.467 (1)º0.44 × 0.24 × 0.04 mm
V = 1004.07 (3) Å3

Data collection

Bruker APEXII diffractometer4527 independent reflections
Radiation source: medium-focus sealed tube3142 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.036
T = 123(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −8→9
Tmin = 0.857, Tmax = 0.988k = −14→14
9295 measured reflectionsl = −17→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)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.161  w = 1/[σ2(Fo2) + (0.0864P)2 + 0.0582P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.001
4527 reflectionsΔρmax = 0.45 e Å3
303 parametersΔρmin = −0.45 e Å3
8 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to measure the somewhat large crystal.

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

xyzUiso*/Ueq
S10.61344 (11)0.11515 (7)0.35357 (6)0.0218 (2)
S20.81997 (11)0.34262 (7)0.04922 (6)0.0250 (2)
N10.7013 (4)0.1337 (3)0.5349 (2)0.0272 (6)
H1N10.721 (5)0.173 (3)0.577 (2)0.044 (11)*
H1N20.680 (6)0.0521 (16)0.568 (3)0.053 (13)*
N20.6604 (3)0.3220 (2)0.39282 (18)0.0179 (5)
H2N0.642 (5)0.354 (3)0.3237 (10)0.042 (11)*
N30.7031 (3)0.3921 (2)0.45314 (18)0.0171 (5)
N40.7758 (4)0.7985 (2)0.45494 (19)0.0208 (5)
H4N0.762 (5)0.8832 (11)0.440 (3)0.040 (11)*
N50.5325 (4)0.4371 (3)0.1469 (2)0.0239 (6)
H5N10.450 (4)0.502 (2)0.147 (3)0.037 (10)*
H5N20.487 (5)0.365 (2)0.154 (3)0.037 (10)*
N60.7531 (4)0.5739 (2)0.0624 (2)0.0223 (5)
H6N0.855 (3)0.590 (4)0.021 (3)0.047 (11)*
N70.6520 (3)0.6664 (2)0.09750 (19)0.0199 (5)
N80.6103 (3)1.0744 (2)0.11636 (19)0.0210 (5)
H8N0.640 (5)1.1508 (18)0.111 (3)0.037 (10)*
C10.6607 (4)0.1932 (3)0.4337 (2)0.0173 (6)
C20.6936 (4)0.5146 (3)0.4011 (2)0.0175 (6)
H20.65790.54590.32960.021*
C30.7347 (4)0.6064 (3)0.4466 (2)0.0161 (6)
C40.7238 (4)0.7375 (3)0.3922 (2)0.0196 (6)
H40.68570.77940.32130.024*
C50.7953 (4)0.5851 (3)0.5511 (2)0.0148 (5)
C60.8287 (4)0.4758 (3)0.6422 (2)0.0188 (6)
H60.81360.39240.64260.023*
C70.8843 (4)0.4918 (3)0.7319 (2)0.0230 (6)
H70.90670.41840.79440.028*
C80.9078 (4)0.6146 (3)0.7319 (2)0.0237 (7)
H80.94640.62270.79430.028*
C90.8759 (4)0.7244 (3)0.6426 (2)0.0211 (6)
H90.89250.80740.64260.025*
C100.8183 (4)0.7082 (3)0.5529 (2)0.0174 (6)
C110.6925 (4)0.4572 (3)0.0883 (2)0.0192 (6)
C120.7333 (4)0.7692 (3)0.0773 (2)0.0189 (6)
H120.85480.77380.04340.023*
C130.6459 (4)0.8771 (3)0.1045 (2)0.0164 (6)
C140.7289 (4)0.9880 (3)0.0867 (2)0.0191 (6)
H140.85271.00170.05760.023*
C150.4594 (4)0.8983 (3)0.1488 (2)0.0156 (6)
C160.3047 (4)0.8256 (3)0.1817 (2)0.0210 (6)
H160.31220.74120.17900.025*
C170.1416 (4)0.8801 (3)0.2180 (2)0.0247 (7)
H170.03720.83120.24140.030*
C180.1256 (4)1.0053 (3)0.2214 (2)0.0245 (7)
H180.01061.04030.24530.029*
C190.2771 (4)1.0783 (3)0.1898 (2)0.0231 (6)
H190.26821.16290.19220.028*
C200.4422 (4)1.0232 (3)0.1547 (2)0.0185 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0312 (4)0.0162 (4)0.0216 (4)−0.0052 (3)−0.0014 (3)−0.0101 (3)
S20.0274 (4)0.0203 (4)0.0321 (4)−0.0073 (3)0.0061 (3)−0.0150 (3)
N10.0433 (17)0.0196 (14)0.0201 (13)−0.0059 (13)−0.0052 (12)−0.0070 (11)
N20.0242 (13)0.0160 (12)0.0171 (12)−0.0055 (10)−0.0017 (10)−0.0089 (10)
N30.0168 (12)0.0196 (13)0.0199 (12)−0.0058 (10)0.0008 (9)−0.0120 (10)
N40.0269 (13)0.0135 (13)0.0233 (13)−0.0045 (11)−0.0012 (10)−0.0072 (10)
N50.0218 (13)0.0207 (14)0.0303 (14)−0.0038 (11)0.0041 (11)−0.0108 (12)
N60.0231 (13)0.0180 (13)0.0280 (14)−0.0031 (11)0.0032 (11)−0.0114 (11)
N70.0221 (12)0.0150 (12)0.0232 (12)0.0008 (10)−0.0018 (10)−0.0081 (10)
N80.0269 (14)0.0162 (13)0.0244 (13)−0.0094 (11)0.0015 (10)−0.0105 (10)
C10.0165 (13)0.0175 (14)0.0188 (14)−0.0034 (11)0.0013 (11)−0.0074 (11)
C20.0157 (13)0.0213 (15)0.0173 (13)−0.0058 (12)0.0007 (10)−0.0079 (11)
C30.0144 (13)0.0178 (14)0.0177 (13)−0.0029 (11)0.0015 (10)−0.0081 (11)
C40.0223 (15)0.0182 (15)0.0188 (14)−0.0035 (12)−0.0005 (11)−0.0069 (12)
C50.0110 (12)0.0163 (14)0.0194 (13)−0.0042 (11)0.0029 (10)−0.0089 (11)
C60.0176 (14)0.0181 (15)0.0220 (14)−0.0036 (12)−0.0004 (11)−0.0080 (12)
C70.0224 (15)0.0254 (16)0.0189 (14)−0.0020 (13)−0.0019 (12)−0.0051 (12)
C80.0193 (14)0.0349 (18)0.0221 (15)−0.0027 (13)−0.0025 (12)−0.0159 (13)
C90.0171 (14)0.0239 (16)0.0279 (15)−0.0020 (12)−0.0003 (12)−0.0163 (13)
C100.0138 (13)0.0175 (15)0.0225 (14)−0.0024 (11)0.0023 (11)−0.0096 (12)
C110.0210 (15)0.0170 (15)0.0215 (14)−0.0031 (12)−0.0030 (11)−0.0083 (12)
C120.0204 (14)0.0175 (15)0.0176 (13)−0.0009 (12)−0.0011 (11)−0.0053 (11)
C130.0206 (14)0.0125 (14)0.0152 (13)−0.0041 (11)−0.0022 (11)−0.0025 (11)
C140.0199 (14)0.0208 (15)0.0177 (13)−0.0047 (12)−0.0003 (11)−0.0072 (12)
C150.0175 (13)0.0149 (14)0.0133 (13)−0.0013 (11)−0.0039 (10)−0.0030 (11)
C160.0237 (15)0.0165 (15)0.0216 (14)−0.0060 (12)−0.0035 (12)−0.0032 (12)
C170.0172 (14)0.0294 (17)0.0258 (15)−0.0066 (13)−0.0009 (12)−0.0065 (13)
C180.0201 (15)0.0312 (18)0.0223 (15)0.0027 (13)−0.0005 (12)−0.0114 (13)
C190.0299 (16)0.0206 (16)0.0207 (14)0.0018 (13)−0.0057 (12)−0.0101 (12)
C200.0237 (15)0.0180 (14)0.0161 (13)−0.0040 (12)−0.0050 (11)−0.0072 (11)

Geometric parameters (Å, °)

S1—C11.696 (3)C4—H40.9500
S2—C111.689 (3)C5—C61.399 (4)
N1—C11.329 (4)C5—C101.415 (4)
N1—H1N10.87 (3)C6—C71.388 (4)
N1—H1N20.89 (3)C6—H60.9500
N2—C11.341 (4)C7—C81.403 (4)
N2—N31.393 (3)C7—H70.9500
N2—H2N0.887 (10)C8—C91.386 (4)
N3—C21.289 (4)C8—H80.9500
N4—C41.365 (3)C9—C101.395 (4)
N4—C101.376 (4)C9—H90.9500
N4—H4N0.886 (10)C12—C131.436 (4)
N5—C111.335 (4)C12—H120.9500
N5—H5N10.88 (3)C13—C141.379 (4)
N5—H5N20.88 (3)C13—C151.446 (4)
N6—C111.344 (4)C14—H140.9500
N6—N71.385 (3)C15—C161.409 (4)
N6—H6N0.88 (3)C15—C201.414 (4)
N7—C121.287 (4)C16—C171.384 (4)
N8—C141.350 (4)C16—H160.9500
N8—C201.384 (4)C17—C181.405 (4)
N8—H8N0.88 (3)C17—H170.9500
C2—C31.443 (4)C18—C191.391 (4)
C2—H20.9500C18—H180.9500
C3—C41.376 (4)C19—C201.391 (4)
C3—C51.443 (4)C19—H190.9500
C1—N1—H1N1124 (3)C8—C7—H7119.5
C1—N1—H1N2120 (3)C9—C8—C7121.4 (3)
H1N1—N1—H1N2114 (4)C9—C8—H8119.3
C1—N2—N3121.7 (2)C7—C8—H8119.3
C1—N2—H2N113 (2)C8—C9—C10117.4 (3)
N3—N2—H2N125 (2)C8—C9—H9121.3
C2—N3—N2113.1 (2)C10—C9—H9121.3
C4—N4—C10109.1 (2)N4—C10—C9129.9 (3)
C4—N4—H4N125 (2)N4—C10—C5108.0 (2)
C10—N4—H4N125 (2)C9—C10—C5122.1 (3)
C11—N5—H5N1121 (2)N5—C11—N6117.1 (3)
C11—N5—H5N2115 (2)N5—C11—S2123.0 (2)
H5N1—N5—H5N2116 (3)N6—C11—S2119.9 (2)
C11—N6—N7120.0 (2)N7—C12—C13122.0 (3)
C11—N6—H6N118 (3)N7—C12—H12119.0
N7—N6—H6N122 (3)C13—C12—H12119.0
C12—N7—N6114.4 (2)C14—C13—C12124.2 (3)
C14—N8—C20109.3 (2)C14—C13—C15105.9 (2)
C14—N8—H8N123 (2)C12—C13—C15129.9 (2)
C20—N8—H8N127 (2)N8—C14—C13110.7 (3)
N1—C1—N2117.8 (2)N8—C14—H14124.6
N1—C1—S1123.6 (2)C13—C14—H14124.6
N2—C1—S1118.6 (2)C16—C15—C20118.8 (3)
N3—C2—C3123.1 (3)C16—C15—C13134.5 (3)
N3—C2—H2118.5C20—C15—C13106.7 (2)
C3—C2—H2118.5C17—C16—C15118.4 (3)
C4—C3—C2123.6 (3)C17—C16—H16120.8
C4—C3—C5106.6 (2)C15—C16—H16120.8
C2—C3—C5129.8 (3)C16—C17—C18122.0 (3)
N4—C4—C3110.1 (3)C16—C17—H17119.0
N4—C4—H4125.0C18—C17—H17119.0
C3—C4—H4125.0C19—C18—C17120.4 (3)
C6—C5—C10119.4 (2)C19—C18—H18119.8
C6—C5—C3134.3 (2)C17—C18—H18119.8
C10—C5—C3106.3 (2)C20—C19—C18117.7 (3)
C7—C6—C5118.6 (3)C20—C19—H19121.2
C7—C6—H6120.7C18—C19—H19121.2
C5—C6—H6120.7N8—C20—C19129.9 (3)
C6—C7—C8121.1 (3)N8—C20—C15107.4 (2)
C6—C7—H7119.5C19—C20—C15122.6 (3)
C1—N2—N3—C2−179.2 (2)C3—C5—C10—C9179.8 (2)
C11—N6—N7—C12173.1 (3)N7—N6—C11—N50.9 (4)
N3—N2—C1—N10.7 (4)N7—N6—C11—S2−177.8 (2)
N3—N2—C1—S1−178.20 (19)N6—N7—C12—C13177.7 (2)
N2—N3—C2—C3−179.0 (2)N7—C12—C13—C14178.5 (3)
N3—C2—C3—C4−179.5 (3)N7—C12—C13—C15−4.9 (5)
N3—C2—C3—C51.5 (5)C20—N8—C14—C13−0.3 (3)
C10—N4—C4—C3−1.2 (3)C12—C13—C14—N8177.4 (2)
C2—C3—C4—N4−178.3 (3)C15—C13—C14—N80.1 (3)
C5—C3—C4—N40.9 (3)C14—C13—C15—C16178.4 (3)
C4—C3—C5—C6178.6 (3)C12—C13—C15—C161.3 (5)
C2—C3—C5—C6−2.3 (5)C14—C13—C15—C200.1 (3)
C4—C3—C5—C10−0.2 (3)C12—C13—C15—C20−177.0 (3)
C2—C3—C5—C10178.9 (3)C20—C15—C16—C170.3 (4)
C10—C5—C6—C7−0.2 (4)C13—C15—C16—C17−177.8 (3)
C3—C5—C6—C7−178.8 (3)C15—C16—C17—C181.0 (4)
C5—C6—C7—C8−0.3 (4)C16—C17—C18—C19−1.4 (4)
C6—C7—C8—C90.3 (4)C17—C18—C19—C200.4 (4)
C7—C8—C9—C100.4 (4)C14—N8—C20—C19−177.0 (3)
C4—N4—C10—C9−179.3 (3)C14—N8—C20—C150.4 (3)
C4—N4—C10—C51.0 (3)C18—C19—C20—N8178.0 (3)
C8—C9—C10—N4179.5 (3)C18—C19—C20—C150.9 (4)
C8—C9—C10—C5−0.9 (4)C16—C15—C20—N8−178.9 (2)
C6—C5—C10—N4−179.5 (2)C13—C15—C20—N8−0.3 (3)
C3—C5—C10—N4−0.5 (3)C16—C15—C20—C19−1.3 (4)
C6—C5—C10—C90.8 (4)C13—C15—C20—C19177.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4n···S1i0.89 (1)2.56 (2)3.383 (3)156 (3)
N8—H8n···S2i0.88 (3)2.49 (2)3.325 (2)157 (3)

Symmetry codes: (i) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2196).

References

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