(E)-4-(Benz­yloxy)benzaldehyde thio­semicarbazone

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

doi:10.1107/S1600536808012671

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Pages o988-o989

doi:10.1107/S1600536808012671

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(E)-4-(Benzyloxy)benzaldehyde thiosemicarbazone

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

^aDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh, ^bDepartment of Chemistry, Rajshahi University of Engineering and Technology, Rajshahi 6205, Bangladesh, ^cDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia, ^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 28 April 2008; accepted 30 April 2008; online 3 May 2008)

In the title compound, C₁₅H₁₅N₃OS, the thiosemicarbazone group adopts an E configuration with respect to the C=N bond. The benzaldehyde thiosemicarbazone fragment is almost planar [maximum deviation = 0.012 (1) Å], while the dihedral angle between the benzyloxy and phenyl rings is 72.48 (5)°. In the crystal structure, molecules are interconnected by N—H⋯N and N—H⋯S hydrogen bonds, forming a two-dimensional network parallel to the bc plane and are further stacked along the a axis by π–π interactions [centroid–centroid separation 3.9043 (7) Å]. The crystal structure is also stabilized by C—H⋯π interactions.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For bond-length data, see: Allen et al. (1987 ). For related structures of thiosemicarbazones, see, for example: John et al. (2003 ); Joseph et al. (2004 ). For applications and bioactivities of thiosemicarbazones, see, for example: Al-Awadi et al. (2008 ); Amoedo et al. (2006 ); Chandra et al., (2001 ); Demertzi et al. (2007 ); Kizilcikli et al. (2004 ); Mirsha et al. (2006 ); Offiong & Martelli (1997 ); Sing et al. (2001 ).

Experimental

Crystal data

C₁₅H₁₅N₃OS
M_r = 285.37
Monoclinic, P 2₁ /c
a = 11.0269 (1) Å
b = 12.6668 (2) Å
c = 10.8774 (1) Å
β = 116.099 (1)°
V = 1364.39 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100.0 (1) K
0.42 × 0.31 × 0.23 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.792, T_max = 0.947
20710 measured reflections
3983 independent reflections
3517 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.03
3983 reflections
193 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1ⁱ	0.880 (16)	2.467 (16)	3.3403 (10)	171.9 (14)
N3—H1N3⋯N1	0.895 (19)	2.229 (18)	2.6104 (16)	105.2 (13)
N3—H1N3⋯S1ⁱⁱ	0.895 (19)	2.815 (17)	3.5285 (11)	137.7 (14)
C10—H10A⋯Cg1ⁱⁱⁱ	0.93	2.97	3.8325 (13)	154
Symmetry codes: (i) -x, -y, -z+2; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1. Cg1 is the centroid of the the C1–C6 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/S1600536808012671/sj2492sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808012671/sj2492Isup2.hkl

checkCIF report

Comment top

The chemistry of thiosemicarbazones have been of immense interest because these compounds provide intriguing chelating patterns, profound biomedical properties, structural diversity and ion-sensing abilities (Al-Awadi et al., 2008; Amoedo et al., 2006; Demertzi et al., 2007; Mirsha et al., 2006; Kizilcikli et al., 2004). Compounds of this type have been used as antibacterial, antifungal and antitumor agents (Sing et al., 2001; Offiong et al., 1997). Due to their long chain structure, they are very flexible and form linkages with a variety of metal ions (Chandra et al., 2001). It was advocated that their flexibility and bioactivity arise because of the presence of the imino group (–N=CH–) in addition to thioamino moities present in the skeleton of the molecule. The title thiosemicarbazone derivative (I) 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 thiosemicarbazone adopts an E conformation with a trans configuration observed about the C═N bond. The benzaldehydethiosemicarbazone fragment is almost planar, maximum deviation 0.012 (1) Å, with the dihedral angle between the hydrazinecarbothioamide unit (S1/N1/N2/N3/C15) and the C8–C13 phenyl ring being 6.59 (5)°. The orientation of the 4-benzyloxy group is indicated by the dihedral angle between the 4-benzyloxy and the C8–C13 phenyl rings being 72.48 (5)Å and the torsion angle C8–O1–C7–C6 of 165.49 (9)°. The C15═S1 and C15—N2 bond distances are typical of a C/db S double bond and a C—N single bond, respectively. The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987) and show similar trends to those of previously reported thiosemicarbazones (John et al., 2003; Joseph et al., 2004). An intramolecular N3-H1N3···N1 hydrogen bond forms a five-membered N3-H1N3-N1—N2—C15 ring, producing an S(5) ring motif (Bernstein et al., 1995).

In the crystal packing (Fig. 2), molecules are interconnected by N—H···N and N—H···S hydrogen bonds (Table 1) into a two-dimensional network parallel to the bc plane and are further stacked along the a-axis by π···π interactions with the distances of Cg₁···Cg₂ = 3.9043 (7) Å: symmetry code x, 1/2 - y, -1/2 + z; Cg₁ and Cg₂ are the centroids of the C1–C6 and C8–C13 phenyl rings, respectively. The crystal also stabilized by C—H···π interactions (Table 1) involving the C1–C6 phenyl ring (centroid Cg₁).

Related literature top

For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For related structures of thiosemicarbazones, see, for example: John et al. (2003); Joseph et al. (2004). For applications and bioactivities of thiosemicarbazones, see, for example: Al-Awadi et al. (2008); Amoedo et al. (2006); Chandra et al., (2001); Demertzi et al. (2007); Kizilcikli et al. (2004); Mirsha et al. (2006); Offiong & Martelli (1997); Sing et al. (2001).

Experimental top

The title compound was synthesized by adding a solution of 4-benzyloxybenzaldehyde (2.12 g, 10 mmol) in ethanol (30 ml) to a hot solution of thiosemicarbazide (0.91 g, 10 mmol) in ethanol (100 ml). The mixture was refluxed for 2 hrs and subsequently cooled to room temperature. The light yellow precipitate of the title compound was separated by filtration, washed with ethanol and dried in vacuo over anhydrous CaCl₂. (Yield: 1.75 g, 61%), and was then dissolved in chloroform (0.11 g in 50 ml) and allowed to stand at room temperature (288–293 K) for 20 days. Yellow single crystals of the title compound were obtained after recrystallization from a solution of chloroform/toluene (30:7 v/v) after 12 days at room temperature, M.p 446 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. The N—H···N intramolecular hydrogen bond is shown as dashed line.
	Fig. 2. The crystal packing of the title compound, viewed along the a axis, showing two-dimensional network parallel to the bc plane. Hydrogen bonds are shown as dashed lines.

(E)-4-(Benzyloxy)benzaldehyde thiosemicarbazone top

Crystal data top

C₁₅H₁₅N₃OS	F(000) = 600
M_r = 285.37	D_x = 1.389 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 446 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.0269 (1) Å	Cell parameters from 3983 reflections
b = 12.6668 (2) Å	θ = 2.1–30.0°
c = 10.8774 (1) Å	µ = 0.24 mm⁻¹
β = 116.099 (1)°	T = 100 K
V = 1364.39 (3) Å³	Block, colorless
Z = 4	0.42 × 0.31 × 0.23 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3983 independent reflections
Radiation source: fine-focus sealed tube	3517 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 2.1°
ω scans	h = −15→14
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −17→17
T_min = 0.792, T_max = 0.947	l = −15→14
20710 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) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0529P)² + 0.4873P] where P = (F_o² + 2F_c²)/3
3983 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₅H₁₅N₃OS	V = 1364.39 (3) Å³
M_r = 285.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0269 (1) Å	µ = 0.24 mm⁻¹
b = 12.6668 (2) Å	T = 100 K
c = 10.8774 (1) Å	0.42 × 0.31 × 0.23 mm
β = 116.099 (1)°

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	3983 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3517 reflections with I > 2σ(I)
T_min = 0.792, T_max = 0.947	R_int = 0.027
20710 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.48 e Å⁻³
3983 reflections	Δρ_min = −0.19 e Å⁻³
193 parameters

Special details top

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

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	−0.13297 (3)	0.13427 (2)	0.97645 (3)	0.01819 (8)
O1	0.32553 (8)	0.07638 (6)	0.33345 (8)	0.01820 (17)
N1	0.04289 (10)	0.10009 (8)	0.73443 (9)	0.01734 (18)
N2	0.00675 (10)	0.08433 (8)	0.83961 (9)	0.01797 (19)
N3	−0.13647 (10)	0.22436 (8)	0.75438 (10)	0.01930 (19)
C1	0.44624 (11)	0.26954 (9)	0.20175 (11)	0.0185 (2)
H1A	0.4399	0.3177	0.2632	0.022*
C2	0.53207 (12)	0.29079 (9)	0.14214 (11)	0.0190 (2)
H2A	0.5835	0.3522	0.1645	0.023*
C3	0.54055 (12)	0.21970 (9)	0.04895 (11)	0.0196 (2)
H3A	0.5973	0.2334	0.0081	0.024*
C4	0.46359 (13)	0.12808 (9)	0.01727 (12)	0.0214 (2)
H4A	0.4685	0.0808	−0.0458	0.026*
C5	0.37939 (12)	0.10629 (9)	0.07858 (11)	0.0206 (2)
H5A	0.3295	0.0441	0.0577	0.025*
C6	0.36955 (11)	0.17766 (9)	0.17140 (11)	0.0174 (2)
C7	0.27374 (12)	0.16007 (10)	0.23367 (11)	0.0203 (2)
H7A	0.2647	0.2244	0.2774	0.024*
H7B	0.1853	0.1410	0.1630	0.024*
C8	0.26799 (11)	0.06651 (8)	0.42162 (10)	0.0158 (2)
C9	0.32639 (11)	−0.00843 (9)	0.52540 (11)	0.0178 (2)
H9A	0.3968	−0.0507	0.5288	0.021*
C10	0.27868 (12)	−0.01940 (9)	0.62342 (11)	0.0177 (2)
H10A	0.3173	−0.0696	0.6922	0.021*
C11	0.17333 (11)	0.04386 (8)	0.62022 (10)	0.0160 (2)
C12	0.11361 (11)	0.11615 (9)	0.51313 (11)	0.0168 (2)
H12A	0.0419	0.1574	0.5084	0.020*
C13	0.15942 (11)	0.12737 (9)	0.41392 (11)	0.0170 (2)
H13A	0.1181	0.1752	0.3426	0.020*
C14	0.12869 (11)	0.03475 (9)	0.72786 (11)	0.0175 (2)
H14A	0.1629	−0.0190	0.7923	0.021*
C15	−0.08583 (11)	0.14858 (8)	0.84847 (11)	0.0156 (2)
H1N2	0.0392 (16)	0.0301 (13)	0.8951 (16)	0.025 (4)*
H1N3	−0.1132 (17)	0.2256 (13)	0.6853 (18)	0.031 (4)*
H2N3	−0.1995 (18)	0.2624 (14)	0.7562 (17)	0.030 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02249 (15)	0.01892 (14)	0.01894 (14)	0.00132 (10)	0.01441 (11)	0.00114 (9)
O1	0.0202 (4)	0.0215 (4)	0.0181 (3)	0.0037 (3)	0.0132 (3)	0.0039 (3)
N1	0.0192 (5)	0.0209 (4)	0.0157 (4)	−0.0012 (3)	0.0111 (4)	0.0006 (3)
N2	0.0217 (5)	0.0200 (4)	0.0176 (4)	0.0032 (4)	0.0136 (4)	0.0035 (3)
N3	0.0189 (5)	0.0224 (5)	0.0197 (4)	0.0039 (4)	0.0114 (4)	0.0045 (4)
C1	0.0198 (5)	0.0211 (5)	0.0152 (4)	0.0028 (4)	0.0082 (4)	0.0004 (4)
C2	0.0184 (5)	0.0208 (5)	0.0170 (5)	−0.0012 (4)	0.0070 (4)	0.0012 (4)
C3	0.0204 (5)	0.0239 (5)	0.0176 (5)	0.0023 (4)	0.0112 (4)	0.0042 (4)
C4	0.0292 (6)	0.0210 (5)	0.0186 (5)	0.0021 (4)	0.0147 (5)	0.0004 (4)
C5	0.0253 (6)	0.0196 (5)	0.0191 (5)	−0.0028 (4)	0.0118 (4)	0.0004 (4)
C6	0.0167 (5)	0.0224 (5)	0.0144 (4)	0.0029 (4)	0.0079 (4)	0.0038 (4)
C7	0.0182 (5)	0.0272 (6)	0.0185 (5)	0.0041 (4)	0.0107 (4)	0.0064 (4)
C8	0.0163 (5)	0.0182 (5)	0.0155 (4)	−0.0017 (4)	0.0095 (4)	−0.0013 (4)
C9	0.0194 (5)	0.0174 (5)	0.0202 (5)	0.0021 (4)	0.0121 (4)	0.0007 (4)
C10	0.0205 (5)	0.0170 (5)	0.0185 (5)	0.0014 (4)	0.0111 (4)	0.0021 (4)
C11	0.0177 (5)	0.0170 (5)	0.0158 (4)	−0.0014 (4)	0.0097 (4)	−0.0011 (4)
C12	0.0151 (5)	0.0206 (5)	0.0163 (5)	0.0010 (4)	0.0083 (4)	0.0001 (4)
C13	0.0157 (5)	0.0210 (5)	0.0152 (4)	0.0017 (4)	0.0077 (4)	0.0021 (4)
C14	0.0200 (5)	0.0181 (5)	0.0171 (4)	−0.0004 (4)	0.0106 (4)	0.0011 (4)
C15	0.0146 (5)	0.0173 (5)	0.0160 (4)	−0.0024 (4)	0.0078 (4)	−0.0010 (4)

Geometric parameters (Å, º) top

S1—C15	1.6964 (11)	C4—H4A	0.9300
O1—C8	1.3688 (12)	C5—C6	1.3946 (15)
O1—C7	1.4430 (13)	C5—H5A	0.9300
N1—C14	1.2826 (14)	C6—C7	1.5014 (15)
N1—N2	1.3815 (12)	C7—H7A	0.9700
N2—C15	1.3417 (14)	C7—H7B	0.9700
N2—H1N2	0.880 (17)	C8—C13	1.3950 (15)
N3—C15	1.3335 (14)	C8—C9	1.3966 (15)
N3—H1N3	0.894 (17)	C9—C10	1.3879 (14)
N3—H2N3	0.853 (18)	C9—H9A	0.9300
C1—C2	1.3886 (15)	C10—C11	1.3990 (15)
C1—C6	1.3903 (16)	C10—H10A	0.9300
C1—H1A	0.9300	C11—C12	1.3979 (15)
C2—C3	1.3894 (15)	C11—C14	1.4606 (14)
C2—H2A	0.9300	C12—C13	1.3856 (14)
C3—C4	1.3887 (16)	C12—H12A	0.9300
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.3884 (16)	C14—H14A	0.9300

C8—O1—C7	116.23 (8)	C6—C7—H7A	109.9
C14—N1—N2	116.20 (9)	O1—C7—H7B	109.9
C15—N2—N1	118.53 (9)	C6—C7—H7B	109.9
C15—N2—H1N2	121.1 (10)	H7A—C7—H7B	108.3
N1—N2—H1N2	120.2 (10)	O1—C8—C13	123.89 (9)
C15—N3—H1N3	118.6 (11)	O1—C8—C9	115.94 (9)
C15—N3—H2N3	117.4 (11)	C13—C8—C9	120.16 (9)
H1N3—N3—H2N3	123.1 (15)	C10—C9—C8	119.55 (10)
C2—C1—C6	121.31 (10)	C10—C9—H9A	120.2
C2—C1—H1A	119.3	C8—C9—H9A	120.2
C6—C1—H1A	119.3	C9—C10—C11	120.98 (10)
C1—C2—C3	119.57 (11)	C9—C10—H10A	119.5
C1—C2—H2A	120.2	C11—C10—H10A	119.5
C3—C2—H2A	120.2	C12—C11—C10	118.52 (9)
C4—C3—C2	119.52 (10)	C12—C11—C14	121.22 (10)
C4—C3—H3A	120.2	C10—C11—C14	120.25 (10)
C2—C3—H3A	120.2	C13—C12—C11	121.11 (10)
C5—C4—C3	120.78 (10)	C13—C12—H12A	119.4
C5—C4—H4A	119.6	C11—C12—H12A	119.4
C3—C4—H4A	119.6	C12—C13—C8	119.60 (10)
C4—C5—C6	120.02 (11)	C12—C13—H13A	120.2
C4—C5—H5A	120.0	C8—C13—H13A	120.2
C6—C5—H5A	120.0	N1—C14—C11	120.71 (10)
C1—C6—C5	118.79 (10)	N1—C14—H14A	119.6
C1—C6—C7	119.49 (10)	C11—C14—H14A	119.6
C5—C6—C7	121.65 (10)	N3—C15—N2	117.16 (9)
O1—C7—C6	108.91 (9)	N3—C15—S1	122.05 (8)
O1—C7—H7A	109.9	N2—C15—S1	120.78 (8)

C14—N1—N2—C15	−177.98 (10)	C13—C8—C9—C10	−2.17 (16)
C6—C1—C2—C3	0.83 (17)	C8—C9—C10—C11	−0.31 (17)
C1—C2—C3—C4	−0.35 (17)	C9—C10—C11—C12	2.21 (16)
C2—C3—C4—C5	−0.62 (18)	C9—C10—C11—C14	−177.07 (10)
C3—C4—C5—C6	1.13 (18)	C10—C11—C12—C13	−1.66 (16)
C2—C1—C6—C5	−0.32 (16)	C14—C11—C12—C13	177.61 (10)
C2—C1—C6—C7	−177.44 (10)	C11—C12—C13—C8	−0.77 (17)
C4—C5—C6—C1	−0.65 (17)	O1—C8—C13—C12	−175.94 (10)
C4—C5—C6—C7	176.40 (11)	C9—C8—C13—C12	2.71 (16)
C8—O1—C7—C6	165.49 (9)	N2—N1—C14—C11	179.67 (9)
C1—C6—C7—O1	−109.78 (11)	C12—C11—C14—N1	−7.05 (17)
C5—C6—C7—O1	73.19 (13)	C10—C11—C14—N1	172.21 (10)
C7—O1—C8—C13	4.11 (15)	N1—N2—C15—N3	−0.34 (15)
C7—O1—C8—C9	−174.59 (10)	N1—N2—C15—S1	−179.21 (8)
O1—C8—C9—C10	176.58 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.880 (16)	2.467 (16)	3.3403 (10)	171.9 (14)
N3—H1N3···N1	0.895 (19)	2.229 (18)	2.6104 (16)	105.2 (13)
N3—H1N3···S1ⁱⁱ	0.895 (19)	2.815 (17)	3.5285 (11)	137.7 (14)
C10—H10A···Cg1ⁱⁱⁱ	0.93	2.97	3.8325 (13)	154

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₃OS
M_r	285.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.0269 (1), 12.6668 (2), 10.8774 (1)
β (°)	116.099 (1)
V (Å³)	1364.39 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.42 × 0.31 × 0.23

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.792, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	20710, 3983, 3517
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.04
No. of reflections	3983
No. of parameters	193
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.19

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
N2—H1N2···S1ⁱ	0.880 (16)	2.467 (16)	3.3403 (10)	171.9 (14)
N3—H1N3···N1	0.895 (19)	2.229 (18)	2.6104 (16)	105.2 (13)
N3—H1N3···S1ⁱⁱ	0.895 (19)	2.815 (17)	3.5285 (11)	137.7 (14)
C10—H10A···Cg1ⁱⁱⁱ	0.93	2.97	3.8325 (13)	154

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

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

Al-Awadi, N. A., Shuaib, N. A., Abbas, A., EI-Sherif, A. A., EI-Dissouky, A. & Al-Saleh, E. (2008). Bioinorg. Chem. Appl. doi:10.1155/2008/479897. Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Amoedo, A., Adrio, L. A., Antelo, J. M., Martinez, J., Pereira, M. T., Fernandez, A. & Vila, J. M. (2006). Eur. J. Inorg. Chem. pp. 3016–3021. Web of Science CSD CrossRef Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chandra, S., Sangeetika & Rathi, A. (2001). J. Saudi Chem. Soc. 5, 175–182. CAS Google Scholar
Demertzi, D. K., Varadinova, T., Genova, P., Souza, P. & Demertzi, M. A. (2007). Bioinorg. Chem. Appl. doi:10.1155/2007/56165. Google Scholar
John, R. P., Sreekanth, A., Kurup, M. R. P., Usman, A., Razak, I. A. & Fun, H. K. (2003). Spectrochim. Acta A, 59, 1349–1358. Web of Science CSD CrossRef Google Scholar
Joseph, M., Suni, V., Nayar, C. R., Kurup, M. R. P. & Fun, H. K. (2004). J. Mol. Struct. 705, 63–70. Web of Science CSD CrossRef CAS Google Scholar
Kizilcikli, I., Ulkuseven, B., Dasdemir, Y. & Akkurt, B. (2004). Synth. React. Inorg. Met.-Org. Chem., 34, 653–665. Web of Science CrossRef CAS Google Scholar
Mirsha, D., Nasker, S., Drew, M. G. B. & Chattopadhay, S. K. (2006). Inorg. Chim. Acta, 359, 585–592. Google Scholar
Offiong, O. E. & Martelli, S. (1997). Transition Met. Chem. 22, 263–269. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sing, N. K., Sing, S. B., Shrivastav, A. & Sing, S. M. (2001). Proc. Indian Acad. Sci. Chem. Sess. 113, 257–273. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar