1H-Indole-3-carbaldehyde thio­semi­carbazone

Rizal, R.M.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536808011082

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages o919-o920

doi:10.1107/S1600536808011082

Open

access

1H-Indole-3-carbaldehyde thiosemicarbazone

Razali M. Rizal,^a Hapipah M. Ali ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 January 2008; accepted 20 April 2008; online 26 April 2008)

The molecules of the title compound, C₁₀H₁₀N₄S, are linked by N—H_indole⋯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

C₁₀H₁₀N₄S
M_r = 218.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.161
S = 1.10
4527 reflections
303 parameters
8 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.45 e Å⁻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) x, y+1, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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); Varshney, Verma & Varshney (1989).

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: 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).

Figures top

	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.

1H-Indole-3-carbaldehyde thiosemicarbazone top

Crystal data top

C₁₀H₁₀N₄S	Z = 4
M_r = 218.28	F(000) = 456
Triclinic, P1	D_x = 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

Data collection top

Bruker APEXII diffractometer	4527 independent reflections
Radiation source: medium-focus sealed tube	3142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→9
T_min = 0.857, T_max = 0.988	k = −14→14
9295 measured reflections	l = −17→17

Refinement top

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(F_o²) + (0.0864P)² + 0.0582P] where P = (F_o² + 2F_c²)/3
4527 reflections	(Δ/σ)_max = 0.001
303 parameters	Δρ_max = 0.45 e Å⁻³
8 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₀H₁₀N₄S	γ = 82.467 (1)°
M_r = 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)°

Data collection top

Bruker APEXII diffractometer	4527 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3142 reflections with I > 2σ(I)
T_min = 0.857, T_max = 0.988	R_int = 0.036
9295 measured reflections

Refinement top

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	Δρ_max = 0.45 e Å⁻³
4527 reflections	Δρ_min = −0.45 e Å⁻³
303 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.857, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9295, 4527, 3142
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bhardwaj, N. C. & Singh, R. V. (1994). Proc. Ind. Acad. Sci. Chem. Sci. 106, 15–22. CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dalvi, K., Pal, M., Garje, S. & Shivram, S. (2004). Indian J. Chem. 43A, 1667–1671. CAS Google Scholar
Doyle, F. P., Ferrier, W., Holland, D. O., Mehta, M. D. & Nayler, J. H. C. (1956). J. Chem. Soc. pp. 2853–2857. CrossRef Web of Science Google Scholar
Fujikawa, F., Yamashita, I., Seno, T., Sasaki, M., Naito, M. & Tsukuma, S. (1966). Yakugaku Zasshi, 86, 801–814. CAS Google Scholar
Garg, A. & Tandon, J. P. (1988). Syn. React. Inorg. Met.-Org. Chem. 18, 705–715. CrossRef CAS Web of Science Google Scholar
Kanoongo, N., Singh, R. V. & Tandon, J. P. (1988). J. Prakt. Chem. (Leipzig), 330, 479–483. CrossRef CAS Google Scholar
Kanoongo, N., Singh, R. V. & Tandon, J. P. (1990). J. Prakt. Chem. (Leipzig), 332, 815–819. CrossRef CAS Web of Science Google Scholar
Kiran, R. V., Singh, J. P. & Tandon, J. P. (1986). Syn. React. Inorg. Met.-Org. Chem. 16, 1341–1350. CrossRef CAS Google Scholar
Kumari, A., Sharma, N., Singh, R. V. & Tandon, J. P. (1992a). Phosphorus, Sulfur Silicon Rel. Elem. 71, 225–229. Google Scholar
Kumari, A., Singh, D., Singh, R. V. & Tandon, J. P. (1993a). Syn. React. Inorg. Met.-Org. Chem. 23, 575–587. CrossRef CAS Web of Science Google Scholar
Kumari, A., Singh, D., Singh, R. V. & Tandon, J. P. (1993b). Phosphorus, Sulfur Silicon Rel. Elem. 80, 117–125. Google Scholar
Kumari, A., Singh, R. V. & Tandon, J. P. (1992b). Phosphorus, Sulfur Silicon Rel. Elem. 66, 195–200. Google Scholar
Libermann, D., Moyeux, M., Rouaix, A., Maillard, J., Hengl, L. & Himbert, J. (1953). Bull. Soc. Chim. Fr. pp. 957–962. Google Scholar
Rodriguez-Argueelles, M. C., Lopez-Silva, E., Sanmartin, J., Pelagatti, P. & Zani, F. (2005). J. Inorg. Biochem. 99, 2231–2239. Web of Science PubMed CAS Google Scholar
Saxena, C., Bhardwaj, N. C., Singh, D. & Singh, R. (1993). Syn. React. Inorg. Met.-Org. Chem. 23, 1391–1405. CrossRef CAS Web of Science Google Scholar
Saxena, C. & Singh, R. V. (1994). Appl. Organomet. Chem. 9, 267–276. CrossRef Web of Science Google Scholar
Saxena, C., Singh, R. V. & Singh, S. (1994). Syn. React. Inorg. Met.-Org. Chem. 24, 1311–1124. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, D. & Singh, R. V. (1990). Main Group Met. Chem. 13, 19–27. CAS Google Scholar
Singh, K., Singh, R. V. & Tandon, J. P. (1987). Syn. React. Inorg. Met.-Org. Chem. 17, 385–398. CrossRef CAS Web of Science Google Scholar
Singh, K., Singh, R. V. & Tandon, J. P. (1988). Polyhedron, 7, 151–154. CrossRef CAS Web of Science Google Scholar
Varshney, S., Singh, H. & Varshney, A. K. (1996). ACGC Chem. Res. Commun. 4, 26–29. CAS Google Scholar
Varshney, A. K. & Tandon, J. P. (1989). Egypt. J. Chem. 32, 109–114. CAS Google Scholar
Varshney, A. K., Verma, P. S. & Varshney, S. (1989). Main Group Met. Chem. 12, 249–257. CAS Google Scholar
Weller, L. E., Sell, H. M. & Gottshall, R. Y. (1954). J. Am. Chem. Soc. 76, 1959–???. Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar