organic compounds
1H-Indole-3-carbaldehyde thiosemicarbazone
aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my
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); Fujikawa et al. (1966); Libermann et al. (1953); Weller et al. (1954). For metal complexes of the compound, see: Bhardwaj & Singh (1994); Dalvi et al. (2004); Garg & Tandon (1988); Kanoongo et al. (1988, 1990); Kiran et al. (1986); Kumari et al. (1992a,b; 1993a,b); Rodriguez-Argueelles et al. (2005); Saxena & Singh (1994); Saxena et al. (1993, 1994); Singh & Singh (1990); Singh et al. (1987, 1988); Varshney & Tandon (1989); Varshney et al. (1989, 1996).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT (Bruker, 2005); data reduction: SAINT; 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).
Supporting information
10.1107/S1600536808011082/rz2196sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808011082/rz2196Isup2.hkl
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.
The carbon-bound H atoms were placed at calculated positions (C–H 0.95 Å), and were included in the
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.Data collection: APEX2 (Bruker, 2005); cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).C10H10N4S | Z = 4 |
Mr = 218.28 | F(000) = 456 |
Triclinic, P1 | Dx = 1.444 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.1893 (1) Å | Cell parameters from 4065 reflections |
b = 11.1654 (2) Å | θ = 3.6–30.8° |
c = 13.5373 (3) Å | µ = 0.29 mm−1 |
α = 68.887 (1)° | T = 123 K |
β = 85.048 (1)° | Wedge, colorless |
γ = 82.467 (1)° | 0.44 × 0.24 × 0.04 mm |
V = 1004.07 (3) Å3 |
Bruker APEXII diffractometer | 4527 independent reflections |
Radiation source: medium-focus sealed tube | 3142 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ϕ and ω scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
Tmin = 0.857, Tmax = 0.988 | k = −14→14 |
9295 measured reflections | l = −17→17 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0864P)2 + 0.0582P] where P = (Fo2 + 2Fc2)/3 |
4527 reflections | (Δ/σ)max = 0.001 |
303 parameters | Δρmax = 0.45 e Å−3 |
8 restraints | Δρmin = −0.45 e Å−3 |
C10H10N4S | γ = 82.467 (1)° |
Mr = 218.28 | V = 1004.07 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 7.1893 (1) Å | Mo Kα radiation |
b = 11.1654 (2) Å | µ = 0.29 mm−1 |
c = 13.5373 (3) Å | T = 123 K |
α = 68.887 (1)° | 0.44 × 0.24 × 0.04 mm |
β = 85.048 (1)° |
Bruker APEXII diffractometer | 4527 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3142 reflections with I > 2σ(I) |
Tmin = 0.857, Tmax = 0.988 | Rint = 0.036 |
9295 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 8 restraints |
wR(F2) = 0.161 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.45 e Å−3 |
4527 reflections | Δρmin = −0.45 e Å−3 |
303 parameters |
Experimental. A medium-focus collimator of 0.8 mm diameter was used on the diffractometer to measure the somewhat large crystal. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.61344 (11) | 0.11515 (7) | 0.35357 (6) | 0.0218 (2) | |
S2 | 0.81997 (11) | 0.34262 (7) | 0.04922 (6) | 0.0250 (2) | |
N1 | 0.7013 (4) | 0.1337 (3) | 0.5349 (2) | 0.0272 (6) | |
H1N1 | 0.721 (5) | 0.173 (3) | 0.577 (2) | 0.044 (11)* | |
H1N2 | 0.680 (6) | 0.0521 (16) | 0.568 (3) | 0.053 (13)* | |
N2 | 0.6604 (3) | 0.3220 (2) | 0.39282 (18) | 0.0179 (5) | |
H2N | 0.642 (5) | 0.354 (3) | 0.3237 (10) | 0.042 (11)* | |
N3 | 0.7031 (3) | 0.3921 (2) | 0.45314 (18) | 0.0171 (5) | |
N4 | 0.7758 (4) | 0.7985 (2) | 0.45494 (19) | 0.0208 (5) | |
H4N | 0.762 (5) | 0.8832 (11) | 0.440 (3) | 0.040 (11)* | |
N5 | 0.5325 (4) | 0.4371 (3) | 0.1469 (2) | 0.0239 (6) | |
H5N1 | 0.450 (4) | 0.502 (2) | 0.147 (3) | 0.037 (10)* | |
H5N2 | 0.487 (5) | 0.365 (2) | 0.154 (3) | 0.037 (10)* | |
N6 | 0.7531 (4) | 0.5739 (2) | 0.0624 (2) | 0.0223 (5) | |
H6N | 0.855 (3) | 0.590 (4) | 0.021 (3) | 0.047 (11)* | |
N7 | 0.6520 (3) | 0.6664 (2) | 0.09750 (19) | 0.0199 (5) | |
N8 | 0.6103 (3) | 1.0744 (2) | 0.11636 (19) | 0.0210 (5) | |
H8N | 0.640 (5) | 1.1508 (18) | 0.111 (3) | 0.037 (10)* | |
C1 | 0.6607 (4) | 0.1932 (3) | 0.4337 (2) | 0.0173 (6) | |
C2 | 0.6936 (4) | 0.5146 (3) | 0.4011 (2) | 0.0175 (6) | |
H2 | 0.6579 | 0.5459 | 0.3296 | 0.021* | |
C3 | 0.7347 (4) | 0.6064 (3) | 0.4466 (2) | 0.0161 (6) | |
C4 | 0.7238 (4) | 0.7375 (3) | 0.3922 (2) | 0.0196 (6) | |
H4 | 0.6857 | 0.7794 | 0.3213 | 0.024* | |
C5 | 0.7953 (4) | 0.5851 (3) | 0.5511 (2) | 0.0148 (5) | |
C6 | 0.8287 (4) | 0.4758 (3) | 0.6422 (2) | 0.0188 (6) | |
H6 | 0.8136 | 0.3924 | 0.6426 | 0.023* | |
C7 | 0.8843 (4) | 0.4918 (3) | 0.7319 (2) | 0.0230 (6) | |
H7 | 0.9067 | 0.4184 | 0.7944 | 0.028* | |
C8 | 0.9078 (4) | 0.6146 (3) | 0.7319 (2) | 0.0237 (7) | |
H8 | 0.9464 | 0.6227 | 0.7943 | 0.028* | |
C9 | 0.8759 (4) | 0.7244 (3) | 0.6426 (2) | 0.0211 (6) | |
H9 | 0.8925 | 0.8074 | 0.6426 | 0.025* | |
C10 | 0.8183 (4) | 0.7082 (3) | 0.5529 (2) | 0.0174 (6) | |
C11 | 0.6925 (4) | 0.4572 (3) | 0.0883 (2) | 0.0192 (6) | |
C12 | 0.7333 (4) | 0.7692 (3) | 0.0773 (2) | 0.0189 (6) | |
H12 | 0.8548 | 0.7738 | 0.0434 | 0.023* | |
C13 | 0.6459 (4) | 0.8771 (3) | 0.1045 (2) | 0.0164 (6) | |
C14 | 0.7289 (4) | 0.9880 (3) | 0.0867 (2) | 0.0191 (6) | |
H14 | 0.8527 | 1.0017 | 0.0576 | 0.023* | |
C15 | 0.4594 (4) | 0.8983 (3) | 0.1488 (2) | 0.0156 (6) | |
C16 | 0.3047 (4) | 0.8256 (3) | 0.1817 (2) | 0.0210 (6) | |
H16 | 0.3122 | 0.7412 | 0.1790 | 0.025* | |
C17 | 0.1416 (4) | 0.8801 (3) | 0.2180 (2) | 0.0247 (7) | |
H17 | 0.0372 | 0.8312 | 0.2414 | 0.030* | |
C18 | 0.1256 (4) | 1.0053 (3) | 0.2214 (2) | 0.0245 (7) | |
H18 | 0.0106 | 1.0403 | 0.2453 | 0.029* | |
C19 | 0.2771 (4) | 1.0783 (3) | 0.1898 (2) | 0.0231 (6) | |
H19 | 0.2682 | 1.1629 | 0.1922 | 0.028* | |
C20 | 0.4422 (4) | 1.0232 (3) | 0.1547 (2) | 0.0185 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0312 (4) | 0.0162 (4) | 0.0216 (4) | −0.0052 (3) | −0.0014 (3) | −0.0101 (3) |
S2 | 0.0274 (4) | 0.0203 (4) | 0.0321 (4) | −0.0073 (3) | 0.0061 (3) | −0.0150 (3) |
N1 | 0.0433 (17) | 0.0196 (14) | 0.0201 (13) | −0.0059 (13) | −0.0052 (12) | −0.0070 (11) |
N2 | 0.0242 (13) | 0.0160 (12) | 0.0171 (12) | −0.0055 (10) | −0.0017 (10) | −0.0089 (10) |
N3 | 0.0168 (12) | 0.0196 (13) | 0.0199 (12) | −0.0058 (10) | 0.0008 (9) | −0.0120 (10) |
N4 | 0.0269 (13) | 0.0135 (13) | 0.0233 (13) | −0.0045 (11) | −0.0012 (10) | −0.0072 (10) |
N5 | 0.0218 (13) | 0.0207 (14) | 0.0303 (14) | −0.0038 (11) | 0.0041 (11) | −0.0108 (12) |
N6 | 0.0231 (13) | 0.0180 (13) | 0.0280 (14) | −0.0031 (11) | 0.0032 (11) | −0.0114 (11) |
N7 | 0.0221 (12) | 0.0150 (12) | 0.0232 (12) | 0.0008 (10) | −0.0018 (10) | −0.0081 (10) |
N8 | 0.0269 (14) | 0.0162 (13) | 0.0244 (13) | −0.0094 (11) | 0.0015 (10) | −0.0105 (10) |
C1 | 0.0165 (13) | 0.0175 (14) | 0.0188 (14) | −0.0034 (11) | 0.0013 (11) | −0.0074 (11) |
C2 | 0.0157 (13) | 0.0213 (15) | 0.0173 (13) | −0.0058 (12) | 0.0007 (10) | −0.0079 (11) |
C3 | 0.0144 (13) | 0.0178 (14) | 0.0177 (13) | −0.0029 (11) | 0.0015 (10) | −0.0081 (11) |
C4 | 0.0223 (15) | 0.0182 (15) | 0.0188 (14) | −0.0035 (12) | −0.0005 (11) | −0.0069 (12) |
C5 | 0.0110 (12) | 0.0163 (14) | 0.0194 (13) | −0.0042 (11) | 0.0029 (10) | −0.0089 (11) |
C6 | 0.0176 (14) | 0.0181 (15) | 0.0220 (14) | −0.0036 (12) | −0.0004 (11) | −0.0080 (12) |
C7 | 0.0224 (15) | 0.0254 (16) | 0.0189 (14) | −0.0020 (13) | −0.0019 (12) | −0.0051 (12) |
C8 | 0.0193 (14) | 0.0349 (18) | 0.0221 (15) | −0.0027 (13) | −0.0025 (12) | −0.0159 (13) |
C9 | 0.0171 (14) | 0.0239 (16) | 0.0279 (15) | −0.0020 (12) | −0.0003 (12) | −0.0163 (13) |
C10 | 0.0138 (13) | 0.0175 (15) | 0.0225 (14) | −0.0024 (11) | 0.0023 (11) | −0.0096 (12) |
C11 | 0.0210 (15) | 0.0170 (15) | 0.0215 (14) | −0.0031 (12) | −0.0030 (11) | −0.0083 (12) |
C12 | 0.0204 (14) | 0.0175 (15) | 0.0176 (13) | −0.0009 (12) | −0.0011 (11) | −0.0053 (11) |
C13 | 0.0206 (14) | 0.0125 (14) | 0.0152 (13) | −0.0041 (11) | −0.0022 (11) | −0.0025 (11) |
C14 | 0.0199 (14) | 0.0208 (15) | 0.0177 (13) | −0.0047 (12) | −0.0003 (11) | −0.0072 (12) |
C15 | 0.0175 (13) | 0.0149 (14) | 0.0133 (13) | −0.0013 (11) | −0.0039 (10) | −0.0030 (11) |
C16 | 0.0237 (15) | 0.0165 (15) | 0.0216 (14) | −0.0060 (12) | −0.0035 (12) | −0.0032 (12) |
C17 | 0.0172 (14) | 0.0294 (17) | 0.0258 (15) | −0.0066 (13) | −0.0009 (12) | −0.0065 (13) |
C18 | 0.0201 (15) | 0.0312 (18) | 0.0223 (15) | 0.0027 (13) | −0.0005 (12) | −0.0114 (13) |
C19 | 0.0299 (16) | 0.0206 (16) | 0.0207 (14) | 0.0018 (13) | −0.0057 (12) | −0.0101 (12) |
C20 | 0.0237 (15) | 0.0180 (14) | 0.0161 (13) | −0.0040 (12) | −0.0050 (11) | −0.0072 (11) |
S1—C1 | 1.696 (3) | C4—H4 | 0.9500 |
S2—C11 | 1.689 (3) | C5—C6 | 1.399 (4) |
N1—C1 | 1.329 (4) | C5—C10 | 1.415 (4) |
N1—H1N1 | 0.87 (3) | C6—C7 | 1.388 (4) |
N1—H1N2 | 0.89 (3) | C6—H6 | 0.9500 |
N2—C1 | 1.341 (4) | C7—C8 | 1.403 (4) |
N2—N3 | 1.393 (3) | C7—H7 | 0.9500 |
N2—H2N | 0.887 (10) | C8—C9 | 1.386 (4) |
N3—C2 | 1.289 (4) | C8—H8 | 0.9500 |
N4—C4 | 1.365 (3) | C9—C10 | 1.395 (4) |
N4—C10 | 1.376 (4) | C9—H9 | 0.9500 |
N4—H4N | 0.886 (10) | C12—C13 | 1.436 (4) |
N5—C11 | 1.335 (4) | C12—H12 | 0.9500 |
N5—H5N1 | 0.88 (3) | C13—C14 | 1.379 (4) |
N5—H5N2 | 0.88 (3) | C13—C15 | 1.446 (4) |
N6—C11 | 1.344 (4) | C14—H14 | 0.9500 |
N6—N7 | 1.385 (3) | C15—C16 | 1.409 (4) |
N6—H6N | 0.88 (3) | C15—C20 | 1.414 (4) |
N7—C12 | 1.287 (4) | C16—C17 | 1.384 (4) |
N8—C14 | 1.350 (4) | C16—H16 | 0.9500 |
N8—C20 | 1.384 (4) | C17—C18 | 1.405 (4) |
N8—H8N | 0.88 (3) | C17—H17 | 0.9500 |
C2—C3 | 1.443 (4) | C18—C19 | 1.391 (4) |
C2—H2 | 0.9500 | C18—H18 | 0.9500 |
C3—C4 | 1.376 (4) | C19—C20 | 1.391 (4) |
C3—C5 | 1.443 (4) | C19—H19 | 0.9500 |
C1—N1—H1N1 | 124 (3) | C8—C7—H7 | 119.5 |
C1—N1—H1N2 | 120 (3) | C9—C8—C7 | 121.4 (3) |
H1N1—N1—H1N2 | 114 (4) | C9—C8—H8 | 119.3 |
C1—N2—N3 | 121.7 (2) | C7—C8—H8 | 119.3 |
C1—N2—H2N | 113 (2) | C8—C9—C10 | 117.4 (3) |
N3—N2—H2N | 125 (2) | C8—C9—H9 | 121.3 |
C2—N3—N2 | 113.1 (2) | C10—C9—H9 | 121.3 |
C4—N4—C10 | 109.1 (2) | N4—C10—C9 | 129.9 (3) |
C4—N4—H4N | 125 (2) | N4—C10—C5 | 108.0 (2) |
C10—N4—H4N | 125 (2) | C9—C10—C5 | 122.1 (3) |
C11—N5—H5N1 | 121 (2) | N5—C11—N6 | 117.1 (3) |
C11—N5—H5N2 | 115 (2) | N5—C11—S2 | 123.0 (2) |
H5N1—N5—H5N2 | 116 (3) | N6—C11—S2 | 119.9 (2) |
C11—N6—N7 | 120.0 (2) | N7—C12—C13 | 122.0 (3) |
C11—N6—H6N | 118 (3) | N7—C12—H12 | 119.0 |
N7—N6—H6N | 122 (3) | C13—C12—H12 | 119.0 |
C12—N7—N6 | 114.4 (2) | C14—C13—C12 | 124.2 (3) |
C14—N8—C20 | 109.3 (2) | C14—C13—C15 | 105.9 (2) |
C14—N8—H8N | 123 (2) | C12—C13—C15 | 129.9 (2) |
C20—N8—H8N | 127 (2) | N8—C14—C13 | 110.7 (3) |
N1—C1—N2 | 117.8 (2) | N8—C14—H14 | 124.6 |
N1—C1—S1 | 123.6 (2) | C13—C14—H14 | 124.6 |
N2—C1—S1 | 118.6 (2) | C16—C15—C20 | 118.8 (3) |
N3—C2—C3 | 123.1 (3) | C16—C15—C13 | 134.5 (3) |
N3—C2—H2 | 118.5 | C20—C15—C13 | 106.7 (2) |
C3—C2—H2 | 118.5 | C17—C16—C15 | 118.4 (3) |
C4—C3—C2 | 123.6 (3) | C17—C16—H16 | 120.8 |
C4—C3—C5 | 106.6 (2) | C15—C16—H16 | 120.8 |
C2—C3—C5 | 129.8 (3) | C16—C17—C18 | 122.0 (3) |
N4—C4—C3 | 110.1 (3) | C16—C17—H17 | 119.0 |
N4—C4—H4 | 125.0 | C18—C17—H17 | 119.0 |
C3—C4—H4 | 125.0 | C19—C18—C17 | 120.4 (3) |
C6—C5—C10 | 119.4 (2) | C19—C18—H18 | 119.8 |
C6—C5—C3 | 134.3 (2) | C17—C18—H18 | 119.8 |
C10—C5—C3 | 106.3 (2) | C20—C19—C18 | 117.7 (3) |
C7—C6—C5 | 118.6 (3) | C20—C19—H19 | 121.2 |
C7—C6—H6 | 120.7 | C18—C19—H19 | 121.2 |
C5—C6—H6 | 120.7 | N8—C20—C19 | 129.9 (3) |
C6—C7—C8 | 121.1 (3) | N8—C20—C15 | 107.4 (2) |
C6—C7—H7 | 119.5 | C19—C20—C15 | 122.6 (3) |
C1—N2—N3—C2 | −179.2 (2) | C3—C5—C10—C9 | 179.8 (2) |
C11—N6—N7—C12 | 173.1 (3) | N7—N6—C11—N5 | 0.9 (4) |
N3—N2—C1—N1 | 0.7 (4) | N7—N6—C11—S2 | −177.8 (2) |
N3—N2—C1—S1 | −178.20 (19) | N6—N7—C12—C13 | 177.7 (2) |
N2—N3—C2—C3 | −179.0 (2) | N7—C12—C13—C14 | 178.5 (3) |
N3—C2—C3—C4 | −179.5 (3) | N7—C12—C13—C15 | −4.9 (5) |
N3—C2—C3—C5 | 1.5 (5) | C20—N8—C14—C13 | −0.3 (3) |
C10—N4—C4—C3 | −1.2 (3) | C12—C13—C14—N8 | 177.4 (2) |
C2—C3—C4—N4 | −178.3 (3) | C15—C13—C14—N8 | 0.1 (3) |
C5—C3—C4—N4 | 0.9 (3) | C14—C13—C15—C16 | 178.4 (3) |
C4—C3—C5—C6 | 178.6 (3) | C12—C13—C15—C16 | 1.3 (5) |
C2—C3—C5—C6 | −2.3 (5) | C14—C13—C15—C20 | 0.1 (3) |
C4—C3—C5—C10 | −0.2 (3) | C12—C13—C15—C20 | −177.0 (3) |
C2—C3—C5—C10 | 178.9 (3) | C20—C15—C16—C17 | 0.3 (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—C18 | 1.0 (4) |
C5—C6—C7—C8 | −0.3 (4) | C16—C17—C18—C19 | −1.4 (4) |
C6—C7—C8—C9 | 0.3 (4) | C17—C18—C19—C20 | 0.4 (4) |
C7—C8—C9—C10 | 0.4 (4) | C14—N8—C20—C19 | −177.0 (3) |
C4—N4—C10—C9 | −179.3 (3) | C14—N8—C20—C15 | 0.4 (3) |
C4—N4—C10—C5 | 1.0 (3) | C18—C19—C20—N8 | 178.0 (3) |
C8—C9—C10—N4 | 179.5 (3) | C18—C19—C20—C15 | 0.9 (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—C9 | 0.8 (4) | C13—C15—C20—C19 | 177.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4n···S1i | 0.89 (1) | 2.56 (2) | 3.383 (3) | 156 (3) |
N8—H8n···S2i | 0.88 (3) | 2.49 (2) | 3.325 (2) | 157 (3) |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C10H10N4S |
Mr | 218.28 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 123 |
a, b, c (Å) | 7.1893 (1), 11.1654 (2), 13.5373 (3) |
α, β, γ (°) | 68.887 (1), 85.048 (1), 82.467 (1) |
V (Å3) | 1004.07 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.44 × 0.24 × 0.04 |
Data collection | |
Diffractometer | Bruker APEXII diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.857, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9295, 4527, 3142 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.161, 1.10 |
No. of reflections | 4527 |
No. of parameters | 303 |
No. of restraints | 8 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.45, −0.45 |
Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4n···S1i | 0.89 (1) | 2.56 (2) | 3.383 (3) | 156 (3) |
N8—H8n···S2i | 0.88 (3) | 2.49 (2) | 3.325 (2) | 157 (3) |
Symmetry code: (i) x, y+1, z. |
Acknowledgements
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.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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.