3-[4-(Methyl­sulfan­yl)benz­yl]-4-{(1E)-[4-(methyl­sulfan­yl)phen­yl]methyl­ene­amino}-4,5-dihydro-1H-1,2,4-triazole-5-thione

Narayana, B.; Jagadeesh Prasad, D.; Sarojini, B.K.; Yathirajan, H.S.; Bolte, M.

doi:10.1107/S1600536807056462

3-[4-(Methylsulfanyl)benzyl]-4-{(1E)-[4-(methylsulfanyl)phenyl]methyleneamino}-4,5-dihydro-1H-1,2,4-triazole-5-thione

B. Narayana, D. Jagadeesh Prasad, B. K. Sarojini, H. S. Yathirajan and M. Bolte

Geometric parameters of the title compound, C₁₈H₁₈N₄S₃, are in the usual ranges. The triazole ring makes dihedral angles of 75.00 (5) and 38.51 (7)° with the two aromatic rings. The molecules crystallize as centrosymmetric dimers connected by N—H

S hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056462/at2474sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056462/at2474Isup2.hkl Contains datablock I

CCDC reference: 674655

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R factor = 0.029
wR factor = 0.077
Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit       P -1
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1     -   C1      ..       5.45 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Schiff bases are synthesized from a primary amine and a carbonyl compound by a nucleophilic addition reaction. They are used as substrates in the preparation of number of industrial and biologically active compounds via ring closure, cycloaddition and replacement reactions. They are also used as substrates in the preparation of number of biologically active compounds (Siddiqui et al.2006). Some Schiff base derivatives are also known to have activities such as antimicrobial (El-Masry et al., 2000; Pandey et al., 1999), antifungal (Singh et al., 1988; Varma et al., 1986), antitumor (Hodnett et al., 1970; Misra et al. 1981; Agarwal et al., 1983) and as herbicides (Samadhiya & Halve, 2001). Condensed 1,2,4-triazoles are biologically important compounds and are used as strating materials for the synthesis of many heterocycles. The crystal structures of 4-[(1E)-benzylideneamino]-3-methyl-2,4-dihydro-1H-1,2,4-triazole-5-thione (Yathirajan, Sarojini et al., 2007), 4-amino-3-(4'-chlorophenyl)-4-H-[1,2,4]-tirazolo-5-thiol (Yathirajan et al., 2005), (E)-2-hydroxy-5-methyl-3-[(4-methyl-2 pyridyl)iminomethyl] benzaldehyde (Büyükgüngör, et al., 2007); (E)-2-hydroxy-5-methyl-3-[(2-pyridylimino) methyl]benzaldehyde (Odabaşoğlu et al., 2007); 1-(4-{[(E)-(4-diethylamino-2-hydroxy phenyl)methylene]amino}phenyl)ethanone (Yathirajan, Vijesh et al., (2007), 2-{(E)-[(2-chloro-5-nitrophenyl)imino]methyl}-5-(diethylamino)phenol (Butcher et al., 2007), 2-bromo-N'-[(E)-(4-fluorophenyl)methylene]-5-methoxybenzohydrazide monohydrate (Narayana et al., 2007), 2-bromo-N'-isopropylidene-5-methoxybenzohydrazide (Sarojini et al., 2007) have been reported. A new Schiff base, C₁₈H₁₈N₄S₃ is prepared and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. The triazole makes dihedral angles of 75.00 (5)Å and 38.51 (7)° with the two aromatic rings. The molecules crystallize as centrosymmetric dimers connected by N—H···S hydrogen bonds.

Related literature top

For related literature, see: Agarwal et al. (1983); Butcher et al. (2007); Büyükgüngör et al. (2007); El-Masry, Fahmy & Abdelwahed (2000); Hodnett & Dunn (1970); Misra et al. (1981); Narayana et al. (2007); Odabaşoğlu et al. (2007); Pandey et al. (1999); Samadhiya & Halve (2001); Sarojini et al. (2007); Siddiqui et al. (2006); Singh & Dash (1988); Varma et al. (1986); Yathirajan et al. (2005); Yathirajan, Sarojini et al. (2007); Yathirajan, Vijesh et al. (2007).

Experimental top

A mixture of 4-amino-5-[4-(methylthio)benzyl]-2,4-dihydro-3H-1,2,4-triazole-3-thione (2.52 g, 0.01 mol) and 4-(methylthio)benzaldehyde (1.52 g, 0.01 mol) in 30 ml of ethanol containing 2 drops of 4 M sulfuric acid was refluxed for about 5 h. On cooling, the solid separated was filtered and recrystallized from acetone (m.p.: 420–424 K). Analysis found: C 55.84, H 4.66, N 14.43, S 24.82%; C₁₈H₁₈N₄S₃ requires: C 55.93, H 4.69, N 14.49, S 24.89%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level. The minor occupied site of the disordered ethyl chain is drawn with open bonds. The intramolecular hydrogen bond is shown as a dashed line.
	Fig. 2. Preparation of the title compound.

3-[4-(Methylsulfanyl)benzyl]-4-{(1E)-[4-(methylsulfanyl)phenyl]methyleneamino}- 4,5-dihydro-1H-1,2,4-triazole-5-thione top

Crystal data top

C₁₈H₁₈N₄S₃	Z = 2
M_r = 386.54	F(000) = 404
Triclinic, P1	D_x = 1.343 Mg m⁻³
Hall symbol: P -1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3269 (7) Å	Cell parameters from 11444 reflections
b = 9.828 (1) Å	θ = 3.8–25.7°
c = 13.6139 (12) Å	µ = 0.40 mm⁻¹
α = 91.093 (7)°	T = 173 K
β = 98.068 (8)°	Block, yellow
γ = 99.789 (8)°	0.28 × 0.26 × 0.21 mm
V = 955.56 (16) Å³

Data collection top

STOE IPDS II two-circle- diffractometer	3555 independent reflections
Radiation source: fine-focus sealed tube	3191 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 25.6°, θ_min = 3.6°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −8→8
T_min = 0.897, T_max = 0.921	k = −11→11
12044 measured reflections	l = −16→16

Refinement top

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0409P)² + 0.3204P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3555 reflections	Δρ_max = 0.24 e Å⁻³
233 parameters	Δρ_min = −0.30 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Crystal data top

C₁₈H₁₈N₄S₃	γ = 99.789 (8)°
M_r = 386.54	V = 955.56 (16) Å³
Triclinic, P1	Z = 2
a = 7.3269 (7) Å	Mo Kα radiation
b = 9.828 (1) Å	µ = 0.40 mm⁻¹
c = 13.6139 (12) Å	T = 173 K
α = 91.093 (7)°	0.28 × 0.26 × 0.21 mm
β = 98.068 (8)°

Data collection top

STOE IPDS II two-circle- diffractometer	3555 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3191 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.921	R_int = 0.036
12044 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.24 e Å⁻³
3555 reflections	Δρ_min = −0.30 e Å⁻³
233 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
S1	1.01643 (5)	0.94490 (4)	0.66117 (3)	0.02266 (11)
S2	−0.09236 (6)	0.51351 (5)	0.14774 (3)	0.03943 (14)
S3	0.57354 (6)	0.82097 (4)	1.22497 (3)	0.03008 (12)
C1	0.8033 (2)	0.87947 (14)	0.59765 (10)	0.0205 (3)
C2	0.5085 (2)	0.76653 (15)	0.55282 (10)	0.0212 (3)
C3	0.3210 (2)	0.68345 (16)	0.56391 (11)	0.0259 (3)
H3A	0.2506	0.7408	0.5997	0.031*
H3B	0.3393	0.6026	0.6040	0.031*
C4	0.6811 (2)	0.87988 (15)	0.79592 (11)	0.0230 (3)
H4	0.7434	0.9660	0.7769	0.028*
N1	0.74922 (17)	0.87201 (13)	0.49904 (9)	0.0246 (3)
H1	0.817 (3)	0.911 (2)	0.4520 (15)	0.039 (5)*
N2	0.56841 (17)	0.80276 (14)	0.46955 (9)	0.0259 (3)
N3	0.64388 (16)	0.81443 (12)	0.63284 (8)	0.0199 (3)
N4	0.61541 (17)	0.78174 (13)	0.73026 (9)	0.0230 (3)
C11	0.20827 (19)	0.63422 (16)	0.46387 (11)	0.0237 (3)
C12	0.1275 (2)	0.72730 (16)	0.40330 (13)	0.0308 (4)
H12	0.1374	0.8201	0.4272	0.037*
C13	0.0329 (2)	0.68735 (17)	0.30888 (13)	0.0334 (4)
H13	−0.0205	0.7527	0.2688	0.040*
C14	0.0160 (2)	0.55068 (16)	0.27268 (12)	0.0266 (3)
C15	0.0897 (2)	0.45557 (15)	0.33402 (12)	0.0266 (3)
H15	0.0748	0.3617	0.3115	0.032*
C16	0.1855 (2)	0.49790 (16)	0.42849 (11)	0.0258 (3)
H16	0.2361	0.4322	0.4695	0.031*
C17	−0.0465 (3)	0.3443 (2)	0.12139 (16)	0.0547 (6)
H17A	0.0883	0.3442	0.1364	0.082*
H17B	−0.0894	0.3183	0.0510	0.082*
H17C	−0.1133	0.2777	0.1623	0.082*
C21	0.6600 (2)	0.85875 (16)	0.90013 (11)	0.0232 (3)
C22	0.5609 (2)	0.73536 (16)	0.93015 (11)	0.0280 (3)
H22	0.5106	0.6619	0.8825	0.034*
C23	0.5354 (2)	0.71928 (16)	1.02835 (11)	0.0285 (3)
H23	0.4674	0.6353	1.0475	0.034*
C24	0.6095 (2)	0.82651 (16)	1.09967 (11)	0.0240 (3)
C25	0.7133 (2)	0.94843 (17)	1.07040 (11)	0.0295 (3)
H25	0.7678	1.0206	1.1184	0.035*
C26	0.7368 (2)	0.96429 (16)	0.97167 (11)	0.0282 (3)
H26	0.8058	1.0479	0.9525	0.034*
C27	0.4774 (3)	0.64210 (19)	1.23845 (13)	0.0392 (4)
H27A	0.3585	0.6170	1.1939	0.059*
H27B	0.4558	0.6282	1.3073	0.059*
H27C	0.5655	0.5838	1.2216	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02176 (19)	0.02459 (19)	0.01955 (18)	−0.00150 (14)	0.00242 (13)	0.00275 (13)
S2	0.0392 (2)	0.0359 (2)	0.0385 (3)	0.00935 (18)	−0.01336 (18)	−0.00501 (18)
S3	0.0344 (2)	0.0375 (2)	0.01671 (19)	0.00034 (17)	0.00564 (15)	−0.00206 (15)
C1	0.0236 (7)	0.0190 (7)	0.0189 (7)	0.0010 (5)	0.0061 (5)	0.0018 (5)
C2	0.0215 (7)	0.0233 (7)	0.0185 (7)	0.0018 (6)	0.0042 (5)	−0.0011 (5)
C3	0.0211 (7)	0.0317 (8)	0.0242 (7)	−0.0009 (6)	0.0080 (6)	0.0019 (6)
C4	0.0241 (7)	0.0245 (7)	0.0218 (7)	0.0046 (6)	0.0077 (6)	0.0017 (6)
N1	0.0217 (6)	0.0319 (7)	0.0173 (6)	−0.0053 (5)	0.0046 (5)	0.0021 (5)
N2	0.0216 (6)	0.0336 (7)	0.0196 (6)	−0.0037 (5)	0.0037 (5)	0.0004 (5)
N3	0.0218 (6)	0.0222 (6)	0.0157 (6)	0.0009 (5)	0.0058 (5)	0.0016 (4)
N4	0.0256 (6)	0.0283 (7)	0.0155 (6)	0.0024 (5)	0.0073 (5)	0.0032 (5)
C11	0.0159 (6)	0.0281 (8)	0.0270 (8)	−0.0002 (5)	0.0077 (6)	0.0005 (6)
C12	0.0273 (8)	0.0234 (8)	0.0406 (9)	0.0062 (6)	−0.0003 (7)	−0.0045 (6)
C13	0.0290 (8)	0.0267 (8)	0.0428 (10)	0.0094 (6)	−0.0064 (7)	0.0006 (7)
C14	0.0173 (7)	0.0277 (8)	0.0329 (8)	0.0019 (6)	−0.0001 (6)	−0.0012 (6)
C15	0.0255 (7)	0.0203 (7)	0.0332 (8)	0.0002 (6)	0.0069 (6)	0.0008 (6)
C16	0.0254 (7)	0.0247 (7)	0.0281 (8)	0.0030 (6)	0.0081 (6)	0.0061 (6)
C17	0.0704 (14)	0.0471 (12)	0.0437 (12)	0.0224 (10)	−0.0146 (10)	−0.0157 (9)
C21	0.0216 (7)	0.0284 (8)	0.0202 (7)	0.0039 (6)	0.0056 (5)	0.0003 (6)
C22	0.0333 (8)	0.0281 (8)	0.0199 (7)	−0.0022 (6)	0.0045 (6)	−0.0044 (6)
C23	0.0318 (8)	0.0292 (8)	0.0224 (8)	−0.0035 (6)	0.0069 (6)	0.0010 (6)
C24	0.0214 (7)	0.0326 (8)	0.0176 (7)	0.0040 (6)	0.0030 (5)	−0.0003 (6)
C25	0.0311 (8)	0.0317 (8)	0.0222 (8)	−0.0030 (6)	0.0033 (6)	−0.0062 (6)
C26	0.0294 (8)	0.0283 (8)	0.0249 (8)	−0.0030 (6)	0.0075 (6)	−0.0011 (6)
C27	0.0449 (10)	0.0436 (10)	0.0262 (8)	−0.0085 (8)	0.0149 (7)	−0.0012 (7)

Geometric parameters (Å, º) top

S1—C1	1.6907 (15)	C13—C14	1.401 (2)
S2—C14	1.7763 (16)	C13—H13	0.9500
S2—C17	1.792 (2)	C14—C15	1.392 (2)
S3—C24	1.7628 (15)	C15—C16	1.395 (2)
S3—C27	1.8022 (18)	C15—H15	0.9500
C1—N1	1.3423 (19)	C16—H16	0.9500
C1—N3	1.3845 (18)	C17—H17A	0.9800
C2—N2	1.3064 (18)	C17—H17B	0.9800
C2—N3	1.3822 (18)	C17—H17C	0.9800
C2—C3	1.5029 (19)	C21—C26	1.396 (2)
C3—C11	1.515 (2)	C21—C22	1.403 (2)
C3—H3A	0.9900	C22—C23	1.384 (2)
C3—H3B	0.9900	C22—H22	0.9500
C4—N4	1.2844 (19)	C23—C24	1.402 (2)
C4—C21	1.464 (2)	C23—H23	0.9500
C4—H4	0.9500	C24—C25	1.402 (2)
N1—N2	1.3831 (17)	C25—C26	1.387 (2)
N1—H1	0.91 (2)	C25—H25	0.9500
N3—N4	1.4060 (16)	C26—H26	0.9500
C11—C16	1.390 (2)	C27—H27A	0.9800
C11—C12	1.394 (2)	C27—H27B	0.9800
C12—C13	1.387 (2)	C27—H27C	0.9800
C12—H12	0.9500

C14—S2—C17	103.29 (9)	C14—C15—C16	120.10 (14)
C24—S3—C27	103.51 (8)	C14—C15—H15	119.9
N1—C1—N3	102.44 (12)	C16—C15—H15	119.9
N1—C1—S1	128.21 (11)	C11—C16—C15	121.32 (14)
N3—C1—S1	129.28 (11)	C11—C16—H16	119.3
N2—C2—N3	110.54 (12)	C15—C16—H16	119.3
N2—C2—C3	126.49 (13)	S2—C17—H17A	109.5
N3—C2—C3	122.97 (12)	S2—C17—H17B	109.5
C2—C3—C11	111.42 (12)	H17A—C17—H17B	109.5
C2—C3—H3A	109.3	S2—C17—H17C	109.5
C11—C3—H3A	109.3	H17A—C17—H17C	109.5
C2—C3—H3B	109.3	H17B—C17—H17C	109.5
C11—C3—H3B	109.3	C26—C21—C22	118.78 (13)
H3A—C3—H3B	108.0	C26—C21—C4	119.66 (13)
N4—C4—C21	119.89 (13)	C22—C21—C4	121.55 (13)
N4—C4—H4	120.1	C23—C22—C21	120.82 (14)
C21—C4—H4	120.1	C23—C22—H22	119.6
C1—N1—N2	114.21 (12)	C21—C22—H22	119.6
C1—N1—H1	126.7 (13)	C22—C23—C24	120.25 (14)
N2—N1—H1	118.9 (12)	C22—C23—H23	119.9
C2—N2—N1	103.96 (11)	C24—C23—H23	119.9
C2—N3—C1	108.76 (11)	C25—C24—C23	119.05 (13)
C2—N3—N4	120.95 (11)	C25—C24—S3	116.97 (11)
C1—N3—N4	129.89 (12)	C23—C24—S3	123.94 (11)
C4—N4—N3	114.65 (12)	C26—C25—C24	120.35 (14)
C16—C11—C12	118.03 (14)	C26—C25—H25	119.8
C16—C11—C3	121.93 (14)	C24—C25—H25	119.8
C12—C11—C3	120.03 (14)	C25—C26—C21	120.72 (14)
C13—C12—C11	121.43 (15)	C25—C26—H26	119.6
C13—C12—H12	119.3	C21—C26—H26	119.6
C11—C12—H12	119.3	S3—C27—H27A	109.5
C12—C13—C14	120.05 (15)	S3—C27—H27B	109.5
C12—C13—H13	120.0	H27A—C27—H27B	109.5
C14—C13—H13	120.0	S3—C27—H27C	109.5
C15—C14—C13	118.98 (15)	H27A—C27—H27C	109.5
C15—C14—S2	124.56 (12)	H27B—C27—H27C	109.5
C13—C14—S2	116.41 (12)

N2—C2—C3—C11	4.5 (2)	C12—C13—C14—C15	2.2 (2)
N3—C2—C3—C11	−174.87 (13)	C12—C13—C14—S2	−175.46 (13)
N3—C1—N1—N2	−1.95 (17)	C17—S2—C14—C15	−8.65 (17)
S1—C1—N1—N2	175.26 (11)	C17—S2—C14—C13	168.82 (14)
N3—C2—N2—N1	1.76 (16)	C13—C14—C15—C16	−2.6 (2)
C3—C2—N2—N1	−177.69 (15)	S2—C14—C15—C16	174.81 (11)
C1—N1—N2—C2	0.17 (18)	C12—C11—C16—C15	1.9 (2)
N2—C2—N3—C1	−3.08 (17)	C3—C11—C16—C15	−176.55 (13)
C3—C2—N3—C1	176.39 (14)	C14—C15—C16—C11	0.5 (2)
N2—C2—N3—N4	−176.48 (13)	N4—C4—C21—C26	178.02 (14)
C3—C2—N3—N4	3.0 (2)	N4—C4—C21—C22	−3.2 (2)
N1—C1—N3—C2	2.92 (15)	C26—C21—C22—C23	1.5 (2)
S1—C1—N3—C2	−174.26 (12)	C4—C21—C22—C23	−177.23 (15)
N1—C1—N3—N4	175.53 (13)	C21—C22—C23—C24	−0.3 (3)
S1—C1—N3—N4	−1.6 (2)	C22—C23—C24—C25	−1.5 (2)
C21—C4—N4—N3	179.85 (12)	C22—C23—C24—S3	176.05 (13)
C2—N3—N4—C4	−142.47 (14)	C27—S3—C24—C25	−169.52 (14)
C1—N3—N4—C4	45.7 (2)	C27—S3—C24—C23	12.87 (17)
C2—C3—C11—C16	104.67 (16)	C23—C24—C25—C26	2.1 (2)
C2—C3—C11—C12	−73.78 (18)	S3—C24—C25—C26	−175.62 (13)
C16—C11—C12—C13	−2.4 (2)	C24—C25—C26—C21	−0.9 (3)
C3—C11—C12—C13	176.13 (14)	C22—C21—C26—C25	−0.9 (2)
C11—C12—C13—C14	0.4 (3)	C4—C21—C26—C25	177.86 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.91 (2)	2.43 (2)	3.3307 (13)	169.7 (17)

Symmetry code: (i) −x+2, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈N₄S₃
M_r	386.54
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.3269 (7), 9.828 (1), 13.6139 (12)
α, β, γ (°)	91.093 (7), 98.068 (8), 99.789 (8)
V (Å³)	955.56 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.28 × 0.26 × 0.21

Data collection
Diffractometer	STOE IPDS II two-circle- diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.897, 0.921
No. of measured, independent and observed [I > 2σ(I)] reflections	12044, 3555, 3191
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.077, 1.05
No. of reflections	3555
No. of parameters	233
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.30

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP in SHELXTL-Plus (Sheldrick, 1991).