N-[(4-Amino-5-sulfanyl­idene-4,5-dihydro-1H-1,2,4-triazol-3-yl)meth­yl]-4-methyl­benzamide

Fun, H.-K.; Yeap, C.S.; Mange, Y.; Isloor, A.M.; Hegde, C.

doi:10.1107/S1600536810035014

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages o2501-o2502

doi:10.1107/S1600536810035014

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N-[(4-Amino-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl]-4-methylbenzamide

Hoong-Kun Fun,^a ^*‡ Chin Sing Yeap,^a § Yatin Mange,^b Arun M. Isloor ^b and Chitrakar Hegde ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bOrganic Chemistry Division, Department of Chemistry, National Institute of Technology–Karnataka, Surathkal, Mangalore 575 025, India, and ^cDepartment of Chemistry, NITTE Meenakshi Institute of Technology, Yelahanka, Bangalore, India
^*Correspondence e-mail: hkfun@usm.my

(Received 30 August 2010; accepted 31 August 2010; online 4 September 2010)

In the title compound, C₁₁H₁₃N₅OS, the dihedral angle between the triazole ring and the benzene ring is 84.21 (7)°. The amino group adopts a pyramidal configuration. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular structure and generates an S(8) ring. In the crystal, molecules are linked by intermolecular N—H⋯O, N—H⋯S, N—H⋯N and C—H⋯S hydrogen bonds into layers lying parallel to the bc plane. The crystal structure is further stabilized by aromatic π–π stacking interactions [centroid–centroid distance = 3.3330 (7) Å].

Related literature

For applications of 1,2,4-triazole derivatives, see: Demirbas et al. (2002 , 2004 ); Tozkoparan et al. (2000 ); Turan-Zitouni et al. (1999 ); Kritsanida et al. (2002 ); Holla et al. (2002 ); Foroumadi et al. (2003 ); Isloor et al. (2009 ); Shujuan et al. (2004 ); Verreck et al. (2003 ); Clemons et al. (2004 ). For related structures, see: Fun et al. (2009a ,b ). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₁H₁₃N₅OS
M_r = 263.32
Monoclinic, P 2₁ /c
a = 14.8148 (1) Å
b = 8.6702 (1) Å
c = 9.8534 (1) Å
β = 104.923 (1)°
V = 1222.96 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.30 × 0.27 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.926, T_max = 0.972
15018 measured reflections
3555 independent reflections
3142 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.093
S = 1.07
3555 reflections
180 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.841 (18)	2.187 (17)	2.9824 (14)	157.7 (17)
N3—H1N3⋯S1ⁱⁱ	0.851 (19)	2.524 (19)	3.2168 (11)	139.2 (15)
N3—H1N3⋯N5ⁱⁱ	0.851 (19)	2.276 (18)	2.9738 (15)	139.3 (16)
N5—H1N5⋯O1	0.843 (19)	2.169 (18)	2.9587 (15)	155.9 (16)
N5—H2N5⋯S1ⁱⁱⁱ	0.880 (18)	2.666 (18)	3.5381 (12)	171.2 (14)
C8—H8A⋯S1^iv	0.97	2.87	3.4456 (12)	119
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) x, y+1, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035014/hb5629sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035014/hb5629Isup2.hkl

checkCIF report

Comment top

The synthesis of 1,2,4-triazole derivatives has been attracting widespread attention due to their diverse biological activities such as antimicrobial, anti-inflammatory, and analgesic antitumorial activities (Demirbas et al., 2004; Tozkoparan et al., 2000; Turan-Zitouni et al., 1999; Demirbas et al., 2002; Kritsanida et al., 2002; Holla et al., 2002; Foroumadi et al., 2003; Isloor et al., 2009). There are some antimicrobial drugs containing a triazole moiety. For instance, fluconazole and itraconazole are used in medical therapy (Shujuan et al., 2004; Verreck et al., 2003). In addition, Vorozole, Letrozole, Fadrozole, and Anastrozole are nonsteroidal drugs used for the treatment of estrogen-dependent breast cancer (Clemons et al., 2004). Prompted by the diverse activities of 1,2,4-triazole derivatives, we have synthesized the title compound to study its crystal structure.

The geometric parameters of the title compound (Fig. 1) are comparable to its related structures (Fun et al., 2009a, b).The dihedral angle between the triazole ring [C9/N2/N3/C10/N4] and the benzene ring [C1–C6] is 84.21 (7)°. The amino group adopts a pyramidal configuration. An intramolecular N5—H1N5···O1 hydrogen bond stabilizes the molecular structure. In the crystal structure, the molecules are linked by intermolecular N1—H1N1···O1, N3—H1N3···S1, N3—H1N3···N5, N5—H2N5···S1 and C8—H8A···S1 hydrogen bonds (Table 1) into two-dimensional planes parallel to bc plane (Fig. 2). Cg1···Cg1 of 3.3330 (7) Å (-x, 2 - y, 1 - z) interactions further stabilize the crystal structure. Cg1 is centroid of the triazole ring.

Related literature top

For applications of 1,2,4-triazole derivatives, see: Demirbas et al. (2002, 2004); Tozkoparan et al. (2000); Turan-Zitouni et al. (1999); Kritsanida et al. (2002); Holla et al. (2002); Foroumadi et al. (2003); Isloor et al. (2009); Shujuan et al. (2004); Verreck et al. (2003); Clemons et al. (2004). For related structures, see: Fun et al. (2009a,b). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of {[(4-methylphenyl)carbonyl]amino}acetic acid (1.93 g, 0.01 mol) and thiocarbohydrazide (1.0 g, 0.01 mol) was taken in a round bottomed flask fitted with a reflux condenser. The mixture was then fused on oil bath for 1 h. The reaction mass was slowly cooled to room temperature and the solid mass was treated with NaHCO₃ solution. The separated solid was collected by filtration and dried. Recrystallization was done from a mixture of ethanol-dioxane to yield colourless blocks of (I). Yield: 2.0 g, 76.0%, m.p. = 493–494 K.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with 50% probability ellipsoids for non-H atoms.
	Fig. 2. The crystal packing of (I), viewed down the c axis, showing molecular planes parallel to bc plane. Intermolecular hydrogen bonds are shown as dashed lines.

N-[(4-Amino-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol- 3-yl)methyl]-4-methylbenzamide top

Crystal data top

C₁₁H₁₃N₅OS	F(000) = 552
M_r = 263.32	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6908 reflections
a = 14.8148 (1) Å	θ = 2.8–32.6°
b = 8.6702 (1) Å	µ = 0.26 mm⁻¹
c = 9.8534 (1) Å	T = 100 K
β = 104.923 (1)°	Block, colourless
V = 1222.96 (2) Å³	0.30 × 0.27 × 0.11 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	3555 independent reflections
Radiation source: fine-focus sealed tube	3142 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 30.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→20
T_min = 0.926, T_max = 0.972	k = −12→11
15018 measured reflections	l = −13→13

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) + (0.0404P)² + 0.7537P] where P = (F_o² + 2F_c²)/3
3555 reflections	(Δ/σ)_max = 0.001
180 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₁H₁₃N₅OS	V = 1222.96 (2) Å³
M_r = 263.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.8148 (1) Å	µ = 0.26 mm⁻¹
b = 8.6702 (1) Å	T = 100 K
c = 9.8534 (1) Å	0.30 × 0.27 × 0.11 mm
β = 104.923 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	3555 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3142 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.972	R_int = 0.023
15018 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 = 0.44 e Å⁻³
3555 reflections	Δρ_min = −0.28 e Å⁻³
180 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.10394 (2)	0.62450 (3)	0.66661 (3)	0.01567 (9)
O1	0.25236 (6)	1.16404 (11)	0.93553 (9)	0.01636 (19)
N1	0.22250 (7)	1.27102 (12)	0.71802 (11)	0.0132 (2)
N2	0.10834 (7)	1.02977 (12)	0.49330 (11)	0.0126 (2)
N3	0.10360 (7)	0.87126 (12)	0.49292 (11)	0.0123 (2)
N4	0.10800 (7)	0.93784 (11)	0.70210 (10)	0.01071 (19)
N5	0.10633 (8)	0.92596 (13)	0.84341 (11)	0.0144 (2)
C1	0.44707 (9)	1.19963 (16)	0.96321 (14)	0.0194 (3)
H1A	0.4293	1.1194	1.0134	0.023*
C2	0.54098 (10)	1.23546 (18)	0.98378 (16)	0.0242 (3)
H2A	0.5857	1.1781	1.0474	0.029*
C3	0.56933 (10)	1.35571 (18)	0.91096 (15)	0.0244 (3)
C4	0.50110 (10)	1.44261 (18)	0.81922 (15)	0.0244 (3)
H4A	0.5188	1.5258	0.7724	0.029*
C5	0.40675 (9)	1.40711 (16)	0.79637 (14)	0.0196 (3)
H5A	0.3620	1.4655	0.7338	0.024*
C6	0.37934 (9)	1.28382 (14)	0.86742 (13)	0.0147 (2)
C7	0.27951 (8)	1.23533 (14)	0.84421 (13)	0.0130 (2)
C8	0.12391 (8)	1.22850 (13)	0.67896 (13)	0.0126 (2)
H8A	0.0896	1.2996	0.6084	0.015*
H8B	0.0990	1.2362	0.7606	0.015*
C9	0.11102 (8)	1.06742 (13)	0.62240 (12)	0.0110 (2)
C10	0.10403 (8)	0.81094 (13)	0.61801 (12)	0.0115 (2)
C11	0.67179 (11)	1.3904 (2)	0.9308 (2)	0.0371 (4)
H11A	0.7038	1.3810	1.0284	0.056*
H11B	0.6789	1.4936	0.8996	0.056*
H11C	0.6978	1.3188	0.8769	0.056*
H1N1	0.2453 (12)	1.299 (2)	0.6521 (18)	0.020 (4)*
H1N3	0.1054 (13)	0.822 (2)	0.419 (2)	0.031 (5)*
H1N5	0.1532 (13)	0.975 (2)	0.8901 (19)	0.025 (5)*
H2N5	0.0541 (12)	0.970 (2)	0.8501 (17)	0.016 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02516 (17)	0.00896 (14)	0.01334 (15)	−0.00100 (11)	0.00578 (12)	−0.00009 (10)
O1	0.0186 (4)	0.0182 (4)	0.0122 (4)	−0.0036 (3)	0.0038 (3)	0.0004 (3)
N1	0.0147 (5)	0.0127 (5)	0.0120 (5)	−0.0028 (4)	0.0030 (4)	0.0000 (4)
N2	0.0135 (5)	0.0108 (4)	0.0127 (5)	−0.0002 (4)	0.0020 (4)	0.0006 (4)
N3	0.0154 (5)	0.0106 (4)	0.0112 (5)	0.0000 (4)	0.0039 (4)	−0.0009 (4)
N4	0.0127 (4)	0.0094 (4)	0.0094 (4)	−0.0003 (3)	0.0018 (3)	0.0000 (3)
N5	0.0197 (5)	0.0143 (5)	0.0098 (5)	−0.0010 (4)	0.0046 (4)	−0.0009 (4)
C1	0.0188 (6)	0.0188 (6)	0.0193 (6)	−0.0019 (5)	0.0023 (5)	−0.0002 (5)
C2	0.0160 (6)	0.0269 (7)	0.0259 (7)	0.0013 (5)	−0.0014 (5)	−0.0030 (6)
C3	0.0165 (6)	0.0337 (8)	0.0237 (7)	−0.0067 (5)	0.0063 (5)	−0.0097 (6)
C4	0.0233 (7)	0.0312 (7)	0.0192 (7)	−0.0125 (6)	0.0063 (5)	−0.0019 (5)
C5	0.0203 (6)	0.0221 (6)	0.0155 (6)	−0.0047 (5)	0.0026 (5)	0.0016 (5)
C6	0.0150 (5)	0.0155 (5)	0.0138 (5)	−0.0019 (4)	0.0038 (4)	−0.0025 (4)
C7	0.0153 (5)	0.0105 (5)	0.0132 (5)	−0.0002 (4)	0.0034 (4)	−0.0018 (4)
C8	0.0130 (5)	0.0100 (5)	0.0143 (5)	0.0006 (4)	0.0024 (4)	−0.0006 (4)
C9	0.0106 (5)	0.0097 (5)	0.0121 (5)	0.0004 (4)	0.0016 (4)	0.0015 (4)
C10	0.0114 (5)	0.0112 (5)	0.0114 (5)	0.0007 (4)	0.0019 (4)	−0.0001 (4)
C11	0.0182 (7)	0.0538 (11)	0.0405 (10)	−0.0117 (7)	0.0099 (7)	−0.0131 (8)

Geometric parameters (Å, º) top

S1—C10	1.6860 (12)	C1—H1A	0.9300
O1—C7	1.2409 (15)	C2—C3	1.390 (2)
N1—C7	1.3469 (16)	C2—H2A	0.9300
N1—C8	1.4587 (15)	C3—C4	1.391 (2)
N1—H1N1	0.843 (18)	C3—C11	1.510 (2)
N2—C9	1.3040 (15)	C4—C5	1.3919 (19)
N2—N3	1.3761 (14)	C4—H4A	0.9300
N3—C10	1.3375 (15)	C5—C6	1.3942 (18)
N3—H1N3	0.85 (2)	C5—H5A	0.9300
N4—C10	1.3695 (15)	C6—C7	1.4974 (17)
N4—C9	1.3780 (14)	C8—C9	1.4975 (16)
N4—N5	1.4028 (14)	C8—H8A	0.9700
N5—H1N5	0.84 (2)	C8—H8B	0.9700
N5—H2N5	0.880 (17)	C11—H11A	0.9600
C1—C2	1.3885 (19)	C11—H11B	0.9600
C1—C6	1.3938 (18)	C11—H11C	0.9600

C7—N1—C8	122.19 (10)	C4—C5—H5A	120.0
C7—N1—H1N1	119.9 (12)	C6—C5—H5A	120.0
C8—N1—H1N1	116.3 (12)	C1—C6—C5	119.31 (12)
C9—N2—N3	103.97 (9)	C1—C6—C7	117.83 (11)
C10—N3—N2	113.57 (10)	C5—C6—C7	122.85 (12)
C10—N3—H1N3	126.8 (14)	O1—C7—N1	122.72 (11)
N2—N3—H1N3	119.4 (14)	O1—C7—C6	121.40 (11)
C10—N4—C9	108.24 (10)	N1—C7—C6	115.87 (10)
C10—N4—N5	122.18 (10)	N1—C8—C9	110.91 (9)
C9—N4—N5	129.57 (10)	N1—C8—H8A	109.5
N4—N5—H1N5	106.3 (12)	C9—C8—H8A	109.5
N4—N5—H2N5	106.4 (11)	N1—C8—H8B	109.5
H1N5—N5—H2N5	110.9 (17)	C9—C8—H8B	109.5
C2—C1—C6	120.09 (13)	H8A—C8—H8B	108.0
C2—C1—H1A	120.0	N2—C9—N4	110.76 (10)
C6—C1—H1A	120.0	N2—C9—C8	124.43 (10)
C1—C2—C3	121.12 (14)	N4—C9—C8	124.61 (10)
C1—C2—H2A	119.4	N3—C10—N4	103.45 (10)
C3—C2—H2A	119.4	N3—C10—S1	129.53 (9)
C2—C3—C4	118.42 (13)	N4—C10—S1	126.98 (9)
C2—C3—C11	120.65 (15)	C3—C11—H11A	109.5
C4—C3—C11	120.93 (15)	C3—C11—H11B	109.5
C3—C4—C5	121.10 (13)	H11A—C11—H11B	109.5
C3—C4—H4A	119.4	C3—C11—H11C	109.5
C5—C4—H4A	119.4	H11A—C11—H11C	109.5
C4—C5—C6	119.90 (13)	H11B—C11—H11C	109.5

C9—N2—N3—C10	−0.49 (13)	C5—C6—C7—N1	25.57 (17)
C6—C1—C2—C3	0.5 (2)	C7—N1—C8—C9	−84.82 (13)
C1—C2—C3—C4	1.7 (2)	N3—N2—C9—N4	−0.06 (12)
C1—C2—C3—C11	−178.05 (14)	N3—N2—C9—C8	175.06 (10)
C2—C3—C4—C5	−2.4 (2)	C10—N4—C9—N2	0.57 (13)
C11—C3—C4—C5	177.38 (14)	N5—N4—C9—N2	−177.73 (11)
C3—C4—C5—C6	0.8 (2)	C10—N4—C9—C8	−174.55 (11)
C2—C1—C6—C5	−2.1 (2)	N5—N4—C9—C8	7.15 (19)
C2—C1—C6—C7	177.06 (12)	N1—C8—C9—N2	−82.22 (14)
C4—C5—C6—C1	1.5 (2)	N1—C8—C9—N4	92.24 (13)
C4—C5—C6—C7	−177.69 (12)	N2—N3—C10—N4	0.81 (13)
C8—N1—C7—O1	0.08 (18)	N2—N3—C10—S1	−177.08 (9)
C8—N1—C7—C6	178.70 (10)	C9—N4—C10—N3	−0.81 (12)
C1—C6—C7—O1	25.05 (17)	N5—N4—C10—N3	177.64 (10)
C5—C6—C7—O1	−155.80 (13)	C9—N4—C10—S1	177.16 (9)
C1—C6—C7—N1	−153.59 (12)	N5—N4—C10—S1	−4.39 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.841 (18)	2.187 (17)	2.9824 (14)	157.7 (17)
N3—H1N3···S1ⁱⁱ	0.851 (19)	2.524 (19)	3.2168 (11)	139.2 (15)
N3—H1N3···N5ⁱⁱ	0.851 (19)	2.276 (18)	2.9738 (15)	139.3 (16)
N5—H1N5···O1	0.843 (19)	2.169 (18)	2.9587 (15)	155.9 (16)
N5—H2N5···S1ⁱⁱⁱ	0.880 (18)	2.666 (18)	3.5381 (12)	171.2 (14)
C8—H8A···S1^iv	0.97	2.87	3.4456 (12)	119

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x, y+1/2, −z+3/2; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₃N₅OS
M_r	263.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.8148 (1), 8.6702 (1), 9.8534 (1)
β (°)	104.923 (1)
V (Å³)	1222.96 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.27 × 0.11

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.926, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	15018, 3555, 3142
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.093, 1.07
No. of reflections	3555
No. of parameters	180
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.28

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ⁱ	0.841 (18)	2.187 (17)	2.9824 (14)	157.7 (17)
N3—H1N3···S1ⁱⁱ	0.851 (19)	2.524 (19)	3.2168 (11)	139.2 (15)
N3—H1N3···N5ⁱⁱ	0.851 (19)	2.276 (18)	2.9738 (15)	139.3 (16)
N5—H1N5···O1	0.843 (19)	2.169 (18)	2.9587 (15)	155.9 (16)
N5—H2N5···S1ⁱⁱⁱ	0.880 (18)	2.666 (18)	3.5381 (12)	171.2 (14)
C8—H8A···S1^iv	0.97	2.87	3.4456 (12)	119

Symmetry codes: (i) x, −y+5/2, z−1/2; (ii) x, −y+3/2, z−1/2; (iii) −x, y+1/2, −z+3/2; (iv) x, y+1, z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5523-2009.

Acknowledgements

HKF thanks Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PFIZIK/811160. CSY thanks USM for the award of a USM Fellowship. AMI is thankful to the Head of the Department of Chemistry and the Director of the National Institute of Technology-Karnataka, Surathkal, India, for providing the research facilities and encouragement.

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