Benzyl 3-[(E,E)-3-phenyl­prop-2-enyl­idene]dithio­carbazate

Tarafder, M.T.H.; Crouse, K.A.; Islam, M.T.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536808013354

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o1042-o1043

doi:10.1107/S1600536808013354

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Benzyl 3-[(E,E)-3-phenylprop-2-enylidene]dithiocarbazate

M. T. H. Tarafder,^a ^* K. A. Crouse,^b M. Toihidul Islam,^c Suchada Chantrapromma ^d ‡ and Hoong-Kun Fun ^e §

^aDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh, ^bDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia, ^cDepartment of Chemistry, Rajshahi University of Engineering and Technology, Rajshahi 6205, Bangladesh, ^dDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^eX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: ttofazzal@yahoo.com

(Received 3 May 2008; accepted 6 May 2008; online 10 May 2008)

The title compound, C₁₇H₁₆N₂S₂, a dithiocarbazate derivative, adopts an EE configuration with respect to the C=C and C=N double bonds of the propenylidine group. The 3-phenylprop-2-enylidene and dithiocarbazate fragments lie essentially in the same plane, with a maximum deviation from that plane of 0.074 (2) Å, while the dihedral angle between the 3-phenylprop-2-enylidene and the benzyl group is 77.78 (7)°. In the crystal structure, molecules are linked by an N—H⋯S hydrogen bond and a weak C—H⋯S interaction involving the terminal thione S atom, forming dimers that are arranged into sheets parallel to the bc plane. The crystal structure is also stabilized by C—H⋯π interactions.

Related literature

For information on values of bond lengths, see Allen et al. (1987 ). For related structures of dithiocarbazate derivatives, see, for example: Crouse et al. (2004 ); Fun et al. (2008 ); Shanmuga Sundara Raj et al. (2000 ). For applications and bioactivities of dithiocarbazate derivatives, see, for example: Ali & Tarafder (1977 ); Ali et al. (2001 , 2002 , 2008 ); Chan et al. (2008 ); Chew et al. (2004 ); Crouse et al. (2004); Tarafder et al. (1978 , 1981 , 2001 , 2008 ).

Experimental

Crystal data

C₁₇H₁₆N₂S₂
M_r = 312.44
Triclinic, $[P \overline 1]$
a = 5.4350 (3) Å
b = 11.6333 (7) Å
c = 13.6289 (8) Å
α = 66.869 (4)°
β = 82.723 (4)°
γ = 87.520 (4)°
V = 786.04 (8) Å³
Z = 2
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 100.0 (1) K
0.58 × 0.19 × 0.05 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.829, T_max = 0.982
16100 measured reflections
3570 independent reflections
2870 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.092
S = 1.07
3570 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S2ⁱ	0.87 (2)	2.53 (2)	3.3714 (19)	165 (2)
C9—H9A⋯S2ⁱ	0.93	2.93	3.7264 (18)	144
C15—H15A⋯Cg1ⁱⁱ	0.93	2.83	3.649 (2)	148
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+2. Cg1 is the centroid of the C1–C6 phenyl ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808013354/sj2494sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808013354/sj2494Isup2.hkl

checkCIF report

Comment top

There has been immense interest in nitrogen-sulfur donor ligands since our report on S-benzyldithiocarbazate (SBDTC) (Ali & Tarafder, 1977). There have also been a number of reports of Schiff bases derived from SBDTC (Ali et al., 2001, 2002, 2008; Chan et al., 2008; Chew et al., 2004; Tarafder et al., 1978, 1981, 2001; Raj et al., 2000). The intriguing coordination chemistry and increasingly important biomedical properties of ligands derived from SBDTC have also received much attention (Ali et al., 2001, 2002; Crouse et al., 2004; Tarafder et al., 2001, 2008). The synthesis and structure of SBDTC have been reported previously (Ali & Tarafder (1977); Shanmuga Sundara Raj et al., 2000). In continuation of our research, the title compound (I), a ligand with both N and S donor atoms, was synthesized and its crystal structure is reported here. (I) is likely to have biomedical properties similar to other nitrogen-sulfur donor ligands studied by our group.

In the title compound (Fig. 1), the 3-phenylprop-2-enylidene amide (N2/C9–C17) and benzyl groups (C1–C7) adopt trans and cis positions with respect to the terminal thione S2 atom about the C8-N1 and C8-S1 bonds, respectively. The 3-phenylprop-2-enylidene (C9–C17) and the dithiocarbazate (N1/N2/S1/S2/C8) fragments is essentially planar with maximum deviation 0.074 (2) Å for C11, while the dihedral angle between the 3-phenylprop-2-enylidene and the benzyl group is 77.78 (7)°. The bond lengths and angles are in normal ranges (Allen et al., 1987). However the C═S distance of 1.7466 (17) Å is longer than the typical value of dithiocarbazate derivatives (Crouse et al., 2004; Fun et al., 2008; Shanmuga Sundara Raj et al., 2000) but being intermediate between the values of 1.82 Å for a C—S single bond and 1.56 Å for a C═S double bond (Suton, 1965). The C9–N2 distance of 1.285 (2) Å indicates a double bond charactor. The bond angles S1–C8–S2 [124.67 (10)°] and N1–C8–S1 [113.76 (13)°] also agree with those observed in trans-cis S-benzyl dithiocarbazate (Shanmuga Sundara Raj et al., 2004).

In the crystal packing (Fig. 2), the molecules are linked by an N1—H1···S2ⁱ hydrogen bond (symmetry code: i = -x, 1-y, 1-z) (Table 1) and a weak C9—H9A···S2ⁱ interaction involving the terminal thione-S atom forming dimers that are arranged into sheets parallel to the bc plane. The crystal is also stabilized by C—H···π interactions (Table 1) involving the C1–C6 phenyl ring (centroid Cg1).

Related literature top

For information on values of bond lengths and angles, see Allen et al. (1987); Suton (1965). For related structures of dithiocarbazate derivatives, see, for example: Crouse et al. (2004); Fun et al. (2008); Shanmuga Sundara Raj et al. (2000). For applications and bioactivities of dithiocarbazate derivatives, see, for example: Ali & Tarafder (1977); Ali et al. (2001, 2002, 2008); Chan et al. (2008); Chew et al. (2004); Crouse et al. (2004); Tarafder et al. (1978, 1981, 2001, 2008). Cg1is the centroid of the C1–C6 phenyl ring.

Experimental top

The title compound was synthesized by adding cinnamaldehyde (1.34 g, 10 mmol) to a solution of S-benzyldithiocarbazate (SBDTC) (1.98 g, 10 mmol) in absolute ethanol (60 ml) and the mixture was refluxed for 40 min. The yellow precipitate, which formed was separated and dried in vacuo over anhydrous CaCl₂ (Yield: 2.1 g, 63%). Yellow needle shaped single crystals of (I) were obtained after recrystallization from absolute ethanol over 15 days; M.p 454 K.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

Benzyl 3-[(E,E)-3-phenylprop-2-enylidene]dithiocarbazate top

Crystal data top

C₁₇H₁₆N₂S₂	Z = 2
M_r = 312.44	F(000) = 328
Triclinic, P1	D_x = 1.320 Mg m⁻³
Hall symbol: -P 1	Melting point: 454 K
a = 5.4350 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6333 (7) Å	Cell parameters from 3570 reflections
c = 13.6289 (8) Å	θ = 1.9–27.5°
α = 66.869 (4)°	µ = 0.33 mm⁻¹
β = 82.723 (4)°	T = 100 K
γ = 87.520 (4)°	Needle, yellow
V = 786.04 (8) Å³	0.58 × 0.19 × 0.05 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3570 independent reflections
Radiation source: fine-focus sealed tube	2870 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
Detector resolution: 8.33 pixels mm^-1	θ_max = 27.5°, θ_min = 1.9°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→15
T_min = 0.829, T_max = 0.982	l = −17→17
16100 measured reflections

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0368P)² + 0.3179P] where P = (F_o² + 2F_c²)/3
3570 reflections	(Δ/σ)_max = 0.001
194 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₁₇H₁₆N₂S₂	γ = 87.520 (4)°
M_r = 312.44	V = 786.04 (8) Å³
Triclinic, P1	Z = 2
a = 5.4350 (3) Å	Mo Kα radiation
b = 11.6333 (7) Å	µ = 0.33 mm⁻¹
c = 13.6289 (8) Å	T = 100 K
α = 66.869 (4)°	0.58 × 0.19 × 0.05 mm
β = 82.723 (4)°

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3570 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2870 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.982	R_int = 0.044
16100 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.29 e Å⁻³
3570 reflections	Δρ_min = −0.27 e Å⁻³
194 parameters

Special details top

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.13630 (8)	0.74106 (4)	0.65560 (3)	0.02137 (13)
S2	−0.23454 (8)	0.66804 (4)	0.47403 (4)	0.02329 (13)
N1	0.1010 (3)	0.56987 (15)	0.60587 (12)	0.0209 (3)
N2	0.2180 (3)	0.55500 (14)	0.69440 (11)	0.0212 (3)
C1	−0.2508 (3)	1.02812 (17)	0.63242 (14)	0.0241 (4)
H1A	−0.1133	1.0404	0.5812	0.029*
C2	−0.2838 (3)	1.10363 (18)	0.68983 (15)	0.0270 (4)
H2A	−0.1690	1.1664	0.6771	0.032*
C3	−0.4872 (3)	1.08611 (18)	0.76620 (15)	0.0265 (4)
H3A	−0.5087	1.1364	0.8054	0.032*
C4	−0.6584 (3)	0.99380 (18)	0.78414 (15)	0.0261 (4)
H4A	−0.7964	0.9824	0.8350	0.031*
C5	−0.6253 (3)	0.91803 (17)	0.72668 (15)	0.0230 (4)
H5A	−0.7413	0.8558	0.7393	0.028*
C6	−0.4207 (3)	0.93393 (16)	0.65043 (14)	0.0203 (4)
C7	−0.3781 (3)	0.84724 (17)	0.59218 (14)	0.0222 (4)
H7A	−0.3250	0.8938	0.5164	0.027*
H7B	−0.5287	0.8014	0.5993	0.027*
C8	−0.0802 (3)	0.65301 (16)	0.57678 (14)	0.0199 (4)
C9	0.3953 (3)	0.47537 (16)	0.71089 (14)	0.0205 (4)
H9A	0.4371	0.4369	0.6628	0.025*
C10	0.5303 (3)	0.44442 (16)	0.80163 (14)	0.0207 (4)
H10A	0.4896	0.4829	0.8497	0.025*
C11	0.7138 (3)	0.36108 (16)	0.81818 (14)	0.0209 (4)
H11A	0.7506	0.3277	0.7662	0.025*
C12	0.8636 (3)	0.31572 (16)	0.90742 (14)	0.0202 (4)
C13	0.8492 (3)	0.36609 (17)	0.98578 (15)	0.0254 (4)
H13A	0.7375	0.4298	0.9830	0.030*
C14	0.9991 (4)	0.32206 (18)	1.06702 (15)	0.0285 (4)
H14A	0.9889	0.3570	1.1182	0.034*
C15	1.1645 (4)	0.22635 (19)	1.07320 (15)	0.0298 (4)
H15A	1.2654	0.1972	1.1282	0.036*
C16	1.1791 (3)	0.17447 (19)	0.99739 (15)	0.0306 (5)
H16A	1.2890	0.1096	1.0016	0.037*
C17	1.0301 (3)	0.21890 (18)	0.91488 (15)	0.0257 (4)
H17A	1.0415	0.1836	0.8639	0.031*
H1N1	0.129 (4)	0.519 (2)	0.5733 (18)	0.038 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0237 (2)	0.0250 (2)	0.0198 (2)	0.00424 (18)	−0.00880 (17)	−0.01190 (19)
S2	0.0242 (2)	0.0305 (3)	0.0194 (2)	0.00284 (19)	−0.00832 (17)	−0.0129 (2)
N1	0.0221 (8)	0.0265 (8)	0.0190 (8)	0.0024 (6)	−0.0071 (6)	−0.0128 (7)
N2	0.0218 (8)	0.0265 (8)	0.0165 (7)	−0.0001 (6)	−0.0052 (6)	−0.0090 (6)
C1	0.0193 (9)	0.0296 (10)	0.0230 (9)	0.0001 (8)	0.0002 (7)	−0.0106 (8)
C2	0.0238 (10)	0.0256 (10)	0.0316 (11)	−0.0046 (8)	−0.0010 (8)	−0.0114 (9)
C3	0.0255 (10)	0.0279 (10)	0.0311 (10)	0.0026 (8)	−0.0030 (8)	−0.0172 (9)
C4	0.0193 (9)	0.0321 (11)	0.0279 (10)	−0.0005 (8)	0.0007 (7)	−0.0136 (9)
C5	0.0182 (9)	0.0250 (10)	0.0260 (10)	−0.0033 (7)	−0.0041 (7)	−0.0094 (8)
C6	0.0189 (9)	0.0223 (9)	0.0195 (9)	0.0031 (7)	−0.0076 (7)	−0.0067 (7)
C7	0.0212 (9)	0.0258 (10)	0.0211 (9)	0.0027 (7)	−0.0081 (7)	−0.0095 (8)
C8	0.0197 (9)	0.0225 (9)	0.0174 (9)	−0.0025 (7)	−0.0018 (7)	−0.0076 (7)
C9	0.0199 (9)	0.0229 (9)	0.0212 (9)	−0.0018 (7)	−0.0027 (7)	−0.0109 (8)
C10	0.0230 (9)	0.0233 (9)	0.0185 (9)	−0.0023 (7)	−0.0039 (7)	−0.0102 (7)
C11	0.0226 (9)	0.0217 (9)	0.0207 (9)	−0.0029 (7)	−0.0034 (7)	−0.0103 (7)
C12	0.0179 (9)	0.0206 (9)	0.0209 (9)	−0.0033 (7)	−0.0032 (7)	−0.0063 (7)
C13	0.0279 (10)	0.0239 (10)	0.0245 (10)	0.0001 (8)	−0.0067 (8)	−0.0085 (8)
C14	0.0361 (11)	0.0285 (10)	0.0214 (10)	−0.0048 (8)	−0.0084 (8)	−0.0083 (8)
C15	0.0236 (10)	0.0373 (11)	0.0217 (10)	−0.0033 (8)	−0.0074 (8)	−0.0025 (9)
C16	0.0227 (10)	0.0351 (11)	0.0276 (10)	0.0061 (8)	−0.0033 (8)	−0.0058 (9)
C17	0.0243 (10)	0.0293 (10)	0.0229 (10)	0.0024 (8)	−0.0017 (7)	−0.0100 (8)

Geometric parameters (Å, º) top

S1—C8	1.7466 (17)	C7—H7A	0.9700
S1—C7	1.8187 (17)	C7—H7B	0.9700
S2—C8	1.6696 (18)	C9—C10	1.433 (2)
N1—C8	1.334 (2)	C9—H9A	0.9300
N1—N2	1.382 (2)	C10—C11	1.337 (2)
N1—H1N1	0.87 (2)	C10—H10A	0.9300
N2—C9	1.285 (2)	C11—C12	1.460 (2)
C1—C2	1.381 (3)	C11—H11A	0.9300
C1—C6	1.390 (3)	C12—C17	1.394 (2)
C1—H1A	0.9300	C12—C13	1.399 (3)
C2—C3	1.381 (3)	C13—C14	1.378 (3)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.379 (3)	C14—C15	1.384 (3)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.384 (3)	C15—C16	1.380 (3)
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.387 (2)	C16—C17	1.387 (3)
C5—H5A	0.9300	C16—H16A	0.9300
C6—C7	1.504 (2)	C17—H17A	0.9300

C8—S1—C7	102.56 (8)	N1—C8—S1	113.76 (13)
C8—N1—N2	120.49 (15)	S2—C8—S1	124.67 (10)
C8—N1—H1N1	118.0 (15)	N2—C9—C10	121.56 (16)
N2—N1—H1N1	120.9 (15)	N2—C9—H9A	119.2
C9—N2—N1	114.00 (14)	C10—C9—H9A	119.2
C2—C1—C6	120.70 (17)	C11—C10—C9	121.02 (16)
C2—C1—H1A	119.6	C11—C10—H10A	119.5
C6—C1—H1A	119.6	C9—C10—H10A	119.5
C1—C2—C3	120.11 (18)	C10—C11—C12	128.25 (16)
C1—C2—H2A	119.9	C10—C11—H11A	115.9
C3—C2—H2A	119.9	C12—C11—H11A	115.9
C4—C3—C2	119.76 (17)	C17—C12—C13	118.27 (16)
C4—C3—H3A	120.1	C17—C12—C11	118.96 (16)
C2—C3—H3A	120.1	C13—C12—C11	122.77 (16)
C3—C4—C5	120.16 (17)	C14—C13—C12	120.56 (17)
C3—C4—H4A	119.9	C14—C13—H13A	119.7
C5—C4—H4A	119.9	C12—C13—H13A	119.7
C4—C5—C6	120.65 (17)	C13—C14—C15	120.60 (18)
C4—C5—H5A	119.7	C13—C14—H14A	119.7
C6—C5—H5A	119.7	C15—C14—H14A	119.7
C5—C6—C1	118.61 (16)	C16—C15—C14	119.64 (17)
C5—C6—C7	120.57 (17)	C16—C15—H15A	120.2
C1—C6—C7	120.76 (16)	C14—C15—H15A	120.2
C6—C7—S1	105.49 (12)	C15—C16—C17	120.11 (18)
C6—C7—H7A	110.6	C15—C16—H16A	119.9
S1—C7—H7A	110.6	C17—C16—H16A	119.9
C6—C7—H7B	110.6	C16—C17—C12	120.81 (18)
S1—C7—H7B	110.6	C16—C17—H17A	119.6
H7A—C7—H7B	108.8	C12—C17—H17A	119.6
N1—C8—S2	121.57 (13)

C8—N1—N2—C9	−177.45 (16)	C7—S1—C8—S2	−2.52 (14)
C6—C1—C2—C3	0.1 (3)	N1—N2—C9—C10	−177.41 (16)
C1—C2—C3—C4	−0.6 (3)	N2—C9—C10—C11	179.74 (17)
C2—C3—C4—C5	0.7 (3)	C9—C10—C11—C12	−177.74 (17)
C3—C4—C5—C6	−0.1 (3)	C10—C11—C12—C17	173.65 (18)
C4—C5—C6—C1	−0.5 (3)	C10—C11—C12—C13	−6.9 (3)
C4—C5—C6—C7	176.79 (16)	C17—C12—C13—C14	1.0 (3)
C2—C1—C6—C5	0.5 (3)	C11—C12—C13—C14	−178.40 (17)
C2—C1—C6—C7	−176.74 (17)	C12—C13—C14—C15	−0.7 (3)
C5—C6—C7—S1	−102.64 (16)	C13—C14—C15—C16	−0.1 (3)
C1—C6—C7—S1	74.54 (18)	C14—C15—C16—C17	0.6 (3)
C8—S1—C7—C6	−175.27 (12)	C15—C16—C17—C12	−0.2 (3)
N2—N1—C8—S2	−176.88 (13)	C13—C12—C17—C16	−0.6 (3)
N2—N1—C8—S1	3.0 (2)	C11—C12—C17—C16	178.89 (17)
C7—S1—C8—N1	177.58 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S2ⁱ	0.87 (2)	2.53 (2)	3.3714 (19)	165 (2)
C9—H9A···S2ⁱ	0.93	2.93	3.7264 (18)	144
C15—H15A···Cg1ⁱⁱ	0.93	2.83	3.649 (2)	148

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂S₂
M_r	312.44
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.4350 (3), 11.6333 (7), 13.6289 (8)
α, β, γ (°)	66.869 (4), 82.723 (4), 87.520 (4)
V (Å³)	786.04 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.58 × 0.19 × 0.05

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.829, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	16100, 3570, 2870
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.093, 1.07
No. of reflections	3570
No. of parameters	194
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.27

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S2ⁱ	0.87 (2)	2.53 (2)	3.3714 (19)	165 (2)
C9—H9A···S2ⁱ	0.93	2.93	3.7264 (18)	144
C15—H15A···Cg1ⁱⁱ	0.93	2.83	3.649 (2)	148

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+2.

Footnotes

‡Additional correspondence author, e-mail: suchada.c@psu.ac.th.

§Additional correspondence author, e-mail: hkfun@usm.my.

Acknowledgements

KAC thanks Universiti Putra Malaysia for financial help. MTHT thanks the University of Rajshahi for the provision of laboratory facilities. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

References

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