1-(1,3-Benzothia­zol-2-yl)-3-(4-chloro­benzo­yl)thio­urea

Yusof, M.S.M.; Aishah, Z.S.; Khairul, W.M.; Yamin, B.M.

doi:10.1107/S160053680903743X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2519

doi:10.1107/S160053680903743X

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1-(1,3-Benzothiazol-2-yl)-3-(4-chlorobenzoyl)thiourea

M. Sukeri M. Yusof,^a ^* Zakaria S. Aishah,^a Wan M. Khairul ^a and Bohari M. Yamin ^b

^aDepartment of Chemical Sciences, Faculty of Science and Technology, Universiti Malaysia Terengganu, Mengabang Telipot, 21030 Kuala Terengganu, Malaysia, and ^bSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
^*Correspondence e-mail: mohdsukeri@umt.edu.my

(Received 25 August 2009; accepted 16 September 2009; online 26 September 2009)

The title compound, C₁₅H₁₀ClN₃OS₂, adopts a cis–trans configuration across the thiourea C—N bonds with respect to the positions of the benzothiazole and 4-chlorobenzoyl groups relative to thiono S atom. An intramolecular N—H⋯O hydrogen bond is present. In the crystal structure, molecules are linked by a weak intermolecular N—H⋯S hydrogen bond, forming centrosymmetric dimers.

Related literature

For the biological activity of thiadiazoles, see: Shukla & Srivastava (2008 ); Göblyös et al. (2005 ); Terzioglu & Gürsoy (2003 ); Rana et al. (2008 ). For their potential as insecticides and fungicides, see: Jian et al. (2005 ). For C—S and C—O bond lengths, see: Saeed & Flörke (2006 ); Yamin & Yusof (2003 ). For the structures of other benzoylthiourea derivatives, see: Dillen et al. (2006 ); Khawar Rauf et al. (2006 ); Weiqun et al. (2004 ).

Experimental

Crystal data

C₁₅H₁₀ClN₃OS₂
M_r = 347.83
Monoclinic, P 2₁ /c
a = 11.726 (2) Å
b = 17.934 (4) Å
c = 7.2617 (16) Å
β = 96.848 (4)°
V = 1516.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 298 K
0.55 × 0.42 × 0.40 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.759, T_max = 0.816
11030 measured reflections
3772 independent reflections
2891 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.05
3772 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.86	1.88	2.6056 (19)	141
N1—H1A⋯S1ⁱ	0.86	2.75	3.5377 (17)	152
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680903743X/vm2003sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680903743X/vm2003Isup2.hkl

checkCIF report

Comment top

For the past few decades, heterocycles featuring thiadiazoles which consist of sulfur and nitrogen have been developed consistenly to act as drugs as well as to play an active role in numerous biological activities (Shukla & Srivastava 2008; Göblyös et al. 2005). These derivatives have been shown to exhibit anticancer, antitubercular and anticonvulsant activities (Terzioglu & Gürsoy 2003; Rana et al. 2008). In agriculture, thiadiazole derivatives have a potential as insecticide and fungicide (Jian et al. 2005). The title compound (I), adopts cis-trans configuration with respect to the positions of the benzothiazole and 4-chlorobenzoyl groups relative to the thiono S atom, across their C—N bonds (Fig 1). The central carbonyl thiourea moiety (S1/C8/N1/N2/C7/O1), phenyl ring (C1—C6) and benzothiazole (S2/N3/C9—C15) groups are all planar, with a maximum deviation of 0.021 (1)Å for atom C10 from the least-squares plane. The central carbonyl thiourea fragment makes dihedral angles of 24.09 (7)° and 4.58 (4)° with the phenyl ring and benzothiazole group, respectively. The two aryl rings are inclined to each other at an angle of 28.42 (8)°. The C8—S1 and C7—O1 bond length show the expected double bond character of 1.6570 (17)Å and 1.2245 (19)Å (Saeed & Flörke 2006; Yamin & Yusof 2003). The N1—C8 is longer than N2—C8 by 0.045 Å, similar to other benzoylthiourea derivatives (Dillen et al. 2006; Khawar Rauf et al. 2006) which is probably due to the intramolecular hydrogen bonding interaction (Weiqun et al. 2004).

There is an intramolecular hydrogen bond, N2—H2···O1 forming a pseudo-six-membered ring, O1···H2—N2—C8—N1—C7—O1 (Fig.1). In the crystal structure, the molecules are linked by a weak intermolecular interaction N1—H1A···S1 (symmetry codes as in Table 1) forming dimers (Fig. 2).

Related literature top

For the biological activity of thiadiazoles, see: Shukla & Srivastava (2008); Göblyös et al. (2005); Terzioglu & Gürsoy (2003); Rana et al. (2008). For their potential as insecticides and fungicides, see: Jian et al. (2005). For C—S and C—O bond lengths, see: Saeed & Flörke (2006); Yamin & Yusof (2003). For other benzoylthiourea derivatives, see: Dillen et al. (2006); Khawar Rauf et al. (2006); Weiqun et al. (2004).

Experimental top

To a stirring acetone solution (75 ml) of 4-chlorobenzoyl chloride (2.0 g, 11.4 mmol) and ammoniumthiocyanate (0.87 g, 11.4 mmol), 2-aminobenzothiazole (1.17 g, 11.4 mmol) in 40 ml of acetone was added dropwise. The solution mixture was put at reflux for 1 h. The resulting solution was poured into a beaker containing some ice blocks. The light yellow precipitate was filtered off and washed with distilled water and cold ethanol before dried under vacuum. Good quality crystals were obtained by recrystallization from DMSO.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 2. Packing diagram of compound (I), viewed down the b axis. The dashed lines denote the N—H···S hydrogen bond.

1-(1,3-Benzothiazol-2-yl)-3-(4-chlorobenzoyl)thiourea top

Crystal data top

C₁₅H₁₀ClN₃OS₂	F(000) = 712
M_r = 347.83	D_x = 1.524 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 906 reflections
a = 11.726 (2) Å	θ = 1.8–28.3°
b = 17.934 (4) Å	µ = 0.53 mm⁻¹
c = 7.2617 (16) Å	T = 298 K
β = 96.848 (4)°	Block, light yellow
V = 1516.1 (6) Å³	0.55 × 0.42 × 0.40 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3772 independent reflections
Radiation source: fine-focus sealed tube	2891 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 83.66 pixels mm^-1	θ_max = 28.3°, θ_min = 1.8°
ω scans	h = −15→15
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −23→20
T_min = 0.759, T_max = 0.816	l = −8→9
11030 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0606P)² + 0.1737P] where P = (F_o² + 2F_c²)/3
3772 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₀ClN₃OS₂	V = 1516.1 (6) Å³
M_r = 347.83	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.726 (2) Å	µ = 0.53 mm⁻¹
b = 17.934 (4) Å	T = 298 K
c = 7.2617 (16) Å	0.55 × 0.42 × 0.40 mm
β = 96.848 (4)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3772 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2891 reflections with I > 2σ(I)
T_min = 0.759, T_max = 0.816	R_int = 0.022
11030 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
3772 reflections	Δρ_min = −0.22 e Å⁻³
199 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
Cl1	0.84415 (5)	0.83795 (3)	0.39677 (9)	0.07175 (19)
S1	0.49665 (4)	0.38829 (3)	0.39437 (8)	0.05844 (16)
S2	0.58802 (4)	0.22891 (2)	0.41252 (6)	0.04563 (13)
O1	0.86117 (10)	0.46684 (7)	0.3645 (2)	0.0549 (3)
N3	0.80322 (12)	0.24282 (8)	0.3637 (2)	0.0474 (3)
N1	0.67029 (11)	0.48112 (8)	0.3894 (2)	0.0450 (3)
H1A	0.6183	0.5141	0.4005	0.054*
N2	0.71709 (11)	0.35696 (7)	0.3786 (2)	0.0434 (3)
H2A	0.7842	0.3750	0.3695	0.052*
C1	0.70106 (14)	0.63867 (10)	0.3181 (3)	0.0491 (4)
H1	0.6291	0.6194	0.2754	0.059*
C2	0.71738 (15)	0.71472 (10)	0.3236 (3)	0.0520 (4)
H2	0.6570	0.7469	0.2855	0.062*
C3	0.82429 (16)	0.74219 (10)	0.3862 (3)	0.0489 (4)
C4	0.91544 (15)	0.69616 (11)	0.4420 (3)	0.0551 (5)
H4	0.9873	0.7159	0.4832	0.066*
C5	0.89835 (14)	0.61965 (10)	0.4358 (3)	0.0507 (4)
H5	0.9594	0.5877	0.4722	0.061*
C6	0.79104 (13)	0.59043 (9)	0.3759 (2)	0.0418 (4)
C7	0.77928 (13)	0.50832 (10)	0.3753 (2)	0.0420 (4)
C8	0.63429 (13)	0.40769 (9)	0.3881 (2)	0.0417 (4)
C9	0.71104 (14)	0.27973 (9)	0.3813 (2)	0.0404 (4)
C10	0.78156 (15)	0.16707 (10)	0.3728 (2)	0.0459 (4)
C11	0.86167 (18)	0.11049 (11)	0.3579 (3)	0.0612 (5)
H11	0.9372	0.1220	0.3421	0.073*
C12	0.82695 (19)	0.03736 (12)	0.3672 (3)	0.0685 (6)
H12	0.8797	−0.0007	0.3568	0.082*
C13	0.7148 (2)	0.01951 (11)	0.3915 (3)	0.0657 (6)
H13	0.6932	−0.0303	0.3964	0.079*
C14	0.63489 (17)	0.07448 (10)	0.4087 (3)	0.0574 (5)
H14	0.5599	0.0624	0.4266	0.069*
C15	0.66891 (15)	0.14852 (9)	0.3988 (2)	0.0447 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0907 (4)	0.0384 (3)	0.0882 (4)	−0.0049 (2)	0.0194 (3)	−0.0016 (2)
S1	0.0365 (2)	0.0450 (3)	0.0947 (4)	−0.00093 (18)	0.0117 (2)	−0.0050 (2)
S2	0.0387 (2)	0.0442 (2)	0.0534 (3)	−0.00318 (16)	0.00325 (18)	0.00143 (18)
O1	0.0381 (6)	0.0427 (7)	0.0842 (10)	0.0047 (5)	0.0088 (6)	−0.0007 (6)
N3	0.0428 (7)	0.0402 (8)	0.0602 (10)	−0.0005 (6)	0.0099 (7)	−0.0024 (6)
N1	0.0356 (7)	0.0381 (7)	0.0618 (9)	0.0029 (5)	0.0076 (6)	−0.0010 (6)
N2	0.0352 (6)	0.0381 (7)	0.0567 (9)	−0.0015 (5)	0.0045 (6)	−0.0020 (6)
C1	0.0366 (8)	0.0454 (9)	0.0649 (12)	0.0015 (7)	0.0046 (8)	0.0055 (8)
C2	0.0449 (9)	0.0453 (10)	0.0664 (12)	0.0083 (7)	0.0085 (8)	0.0083 (8)
C3	0.0570 (10)	0.0360 (8)	0.0557 (11)	−0.0018 (7)	0.0150 (8)	0.0002 (7)
C4	0.0428 (9)	0.0491 (10)	0.0727 (13)	−0.0069 (8)	0.0042 (8)	−0.0027 (9)
C5	0.0361 (8)	0.0456 (10)	0.0696 (12)	0.0023 (7)	0.0037 (8)	0.0028 (8)
C6	0.0355 (7)	0.0401 (9)	0.0503 (10)	0.0012 (6)	0.0071 (7)	0.0008 (7)
C7	0.0353 (7)	0.0438 (9)	0.0469 (9)	0.0007 (6)	0.0043 (7)	0.0009 (7)
C8	0.0391 (8)	0.0404 (8)	0.0455 (9)	0.0001 (6)	0.0043 (7)	−0.0014 (7)
C9	0.0387 (8)	0.0399 (8)	0.0419 (9)	−0.0021 (6)	0.0018 (6)	−0.0021 (6)
C10	0.0486 (9)	0.0411 (9)	0.0476 (10)	0.0009 (7)	0.0034 (7)	−0.0031 (7)
C11	0.0588 (11)	0.0462 (10)	0.0798 (14)	0.0061 (8)	0.0135 (10)	−0.0040 (9)
C12	0.0754 (14)	0.0442 (11)	0.0844 (16)	0.0115 (10)	0.0034 (12)	−0.0080 (10)
C13	0.0804 (15)	0.0391 (10)	0.0735 (14)	−0.0046 (10)	−0.0076 (11)	0.0004 (9)
C14	0.0605 (11)	0.0462 (10)	0.0628 (12)	−0.0098 (9)	−0.0035 (9)	0.0046 (8)
C15	0.0482 (9)	0.0414 (9)	0.0427 (9)	−0.0020 (7)	−0.0018 (7)	0.0006 (7)

Geometric parameters (Å, º) top

Cl1—C3	1.7334 (19)	C2—H2	0.9300
S1—C8	1.6570 (17)	C3—C4	1.373 (3)
S2—C15	1.7352 (18)	C4—C5	1.386 (3)
S2—C9	1.7438 (17)	C4—H4	0.9300
O1—C7	1.2245 (19)	C5—C6	1.384 (2)
N3—C9	1.287 (2)	C5—H5	0.9300
N3—C10	1.385 (2)	C6—C7	1.479 (2)
N1—C8	1.383 (2)	C10—C15	1.397 (2)
N1—C7	1.383 (2)	C10—C11	1.396 (3)
N1—H1A	0.8600	C11—C12	1.377 (3)
N2—C8	1.338 (2)	C11—H11	0.9300
N2—C9	1.387 (2)	C12—C13	1.385 (3)
N2—H2A	0.8600	C12—H12	0.9300
C1—C2	1.377 (2)	C13—C14	1.376 (3)
C1—C6	1.390 (2)	C13—H13	0.9300
C1—H1	0.9300	C14—C15	1.391 (2)
C2—C3	1.373 (3)	C14—H14	0.9300

C15—S2—C9	87.73 (8)	O1—C7—C6	122.10 (15)
C9—N3—C10	109.80 (14)	N1—C7—C6	115.95 (14)
C8—N1—C7	128.28 (14)	N2—C8—N1	115.16 (14)
C8—N1—H1A	115.9	N2—C8—S1	125.01 (13)
C7—N1—H1A	115.9	N1—C8—S1	119.83 (12)
C8—N2—C9	129.75 (14)	N3—C9—N2	117.86 (15)
C8—N2—H2A	115.1	N3—C9—S2	117.51 (13)
C9—N2—H2A	115.1	N2—C9—S2	124.62 (12)
C2—C1—C6	120.65 (16)	N3—C10—C15	114.96 (15)
C2—C1—H1	119.7	N3—C10—C11	125.47 (17)
C6—C1—H1	119.7	C15—C10—C11	119.57 (17)
C3—C2—C1	118.89 (16)	C12—C11—C10	118.9 (2)
C3—C2—H2	120.6	C12—C11—H11	120.6
C1—C2—H2	120.6	C10—C11—H11	120.6
C4—C3—C2	122.00 (17)	C11—C12—C13	121.1 (2)
C4—C3—Cl1	119.14 (15)	C11—C12—H12	119.4
C2—C3—Cl1	118.86 (14)	C13—C12—H12	119.4
C3—C4—C5	118.75 (17)	C14—C13—C12	120.87 (19)
C3—C4—H4	120.6	C14—C13—H13	119.6
C5—C4—H4	120.6	C12—C13—H13	119.6
C6—C5—C4	120.48 (16)	C13—C14—C15	118.47 (19)
C6—C5—H5	119.8	C13—C14—H14	120.8
C4—C5—H5	119.8	C15—C14—H14	120.8
C5—C6—C1	119.21 (16)	C14—C15—C10	121.07 (17)
C5—C6—C7	117.30 (14)	C14—C15—S2	128.91 (15)
C1—C6—C7	123.48 (15)	C10—C15—S2	110.01 (13)
O1—C7—N1	121.94 (16)

C6—C1—C2—C3	0.3 (3)	C10—N3—C9—S2	0.4 (2)
C1—C2—C3—C4	0.5 (3)	C8—N2—C9—N3	177.61 (17)
C1—C2—C3—Cl1	−178.90 (15)	C8—N2—C9—S2	−4.0 (3)
C2—C3—C4—C5	−0.4 (3)	C15—S2—C9—N3	−0.44 (15)
Cl1—C3—C4—C5	179.00 (15)	C15—S2—C9—N2	−178.82 (15)
C3—C4—C5—C6	−0.5 (3)	C9—N3—C10—C15	−0.2 (2)
C4—C5—C6—C1	1.4 (3)	C9—N3—C10—C11	179.64 (19)
C4—C5—C6—C7	−179.30 (17)	N3—C10—C11—C12	−179.08 (18)
C2—C1—C6—C5	−1.3 (3)	C15—C10—C11—C12	0.8 (3)
C2—C1—C6—C7	179.44 (17)	C10—C11—C12—C13	−0.3 (3)
C8—N1—C7—O1	−2.2 (3)	C11—C12—C13—C14	−0.5 (3)
C8—N1—C7—C6	178.38 (16)	C12—C13—C14—C15	0.8 (3)
C5—C6—C7—O1	−24.7 (3)	C13—C14—C15—C10	−0.3 (3)
C1—C6—C7—O1	154.64 (18)	C13—C14—C15—S2	179.10 (15)
C5—C6—C7—N1	154.75 (16)	N3—C10—C15—C14	179.37 (16)
C1—C6—C7—N1	−25.9 (2)	C11—C10—C15—C14	−0.5 (3)
C9—N2—C8—N1	177.45 (16)	N3—C10—C15—S2	−0.1 (2)
C9—N2—C8—S1	−3.6 (3)	C11—C10—C15—S2	−179.97 (15)
C7—N1—C8—N2	2.7 (3)	C9—S2—C15—C14	−179.14 (18)
C7—N1—C8—S1	−176.34 (14)	C9—S2—C15—C10	0.28 (13)
C10—N3—C9—N2	178.94 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.88	2.6056 (19)	141
N1—H1A···S1ⁱ	0.86	2.75	3.5377 (17)	152
C5—H5···O1ⁱⁱ	0.93	2.49	3.389 (2)	163

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₀ClN₃OS₂
M_r	347.83
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.726 (2), 17.934 (4), 7.2617 (16)
β (°)	96.848 (4)
V (Å³)	1516.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.55 × 0.42 × 0.40

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.759, 0.816
No. of measured, independent and observed [I > 2σ(I)] reflections	11030, 3772, 2891
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.05
No. of reflections	3772
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PARST (Nardelli, 1995) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.86	1.88	2.6056 (19)	141
N1—H1A···S1ⁱ	0.86	2.75	3.5377 (17)	152

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

The authors would like to thank the Malaysian Government, Universiti Kebangsaan Malaysia, Universiti Malaysia Terengganu and the Ministry of Science, Technology and Innovation for the research grants e-science fund 52022.

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