1H-Indole-3-carbaldehyde thio-semi-carbazone.

The mol-ecules of the title compound, C(10)H(10)N(4)S, are linked by N-H(indole)⋯S hydrogen bonds to form a linear hydrogen-bonded chain. There are two independent mol-ecules 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

C10H10N4S

M = 218.28

Triclinic,

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 ▶) 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 ▶); cell refinement: 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 ▶).

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

C10H10N4S	Z = 4
Mr = 218.28	F000 = 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 = 3.6–30.8º
c = 13.5373 (3) Å	µ = 0.29 mm−1
α = 68.887 (1)º	T = 123 (2) K
β = 85.048 (1)º	Wedge, colorless
γ = 82.467 (1)º	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)
Monochromator: graphite	Rint = 0.036
T = 123(2) K	θmax = 27.5º
φ and ω scans	θmin = 1.6º
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	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H 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 reflections	Δρmax = 0.45 e Å−3
303 parameters	Δρmin = −0.45 e Å−3
8 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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)

Table 1

Hydrogen-bond geometry (Å, °)

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) .