4-Amino-3-(1-naphthyl­oxymeth­yl)-1H-1,2,4-triazole-5(4H)-thione

Fun, H.-K.; Quah, C.K.; Vijesh, A.M.; Malladi, S.; Isloor, A.M.

doi:10.1107/S1600536809051368

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Pages o29-o30

doi:10.1107/S1600536809051368

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4-Amino-3-(1-naphthyloxymethyl)-1H-1,2,4-triazole-5(4H)-thione

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § A. M. Vijesh,^b,^c Shridhar Malladi ^c and Arun M. Isloor ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bSeQuent Scientific Limited, No. 120 A & B, Industrial Area, Baikampady, New Mangalore, Karnataka 575 011, India, and ^cDepartment of Chemistry, National Institute of Technology-Karnataka, Surathkal, Mangalore 575 025, India
^*Correspondence e-mail: hkfun@usm.my

(Received 26 November 2009; accepted 28 November 2009; online 4 December 2009)

In the title compound, C₁₃H₁₂N₄OS, the dihedral angle between the triazole and naphthalene ring systems is 67.42 (5)°. In the crystal, adjacent molecules are linked via two pairs of intermolecular N—H⋯S interactions, forming R²₂(8) and R²₂(10) ring motifs. Weak C—H⋯S interactions generate infinite chains along [001] and the structure is further consolidated by C–H⋯π bonds and aromatic π⋯π stacking interactions [distance between the centroids of the triazole rings = 3.2479 (7) Å].

Related literature

For general background to and the pharmacological activity of triazole derivatives, see: Amir et al. (2008 ); Sztanke et al. (2008 ); Kuş et al. (2008 ); Padmavathi et al. (2008 ); Isloor et al. (2009 ). For a related structure, see: Fun et al. (2009 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ). For the preparation, see: Suresh (1992 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₃H₁₂N₄OS
M_r = 272.33
Monoclinic, P 2₁ /c
a = 7.0023 (1) Å
b = 24.0785 (4) Å
c = 8.0915 (1) Å
β = 113.404 (1)°
V = 1252.02 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 100 K
0.38 × 0.23 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.908, T_max = 0.983
24326 measured reflections
5826 independent reflections
4223 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.122
S = 1.03
5826 reflections
220 parameters
All H-atom parameters refined
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S1ⁱ	0.89 (2)	2.39 (2)	3.2857 (11)	176.2 (14)
N4—H1N4⋯S1ⁱⁱ	0.90 (2)	2.62 (2)	3.5075 (12)	167.3 (19)
C12—H12A⋯S1ⁱⁱ	0.96 (2)	2.836 (18)	3.5368 (13)	130.3 (12)
C9—H9A⋯Cg1ⁱⁱⁱ	0.964 (17)	2.794 (18)	3.6345 (14)	146.8 (14)
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y, -z; (iii) $[x, -y-{\script{3\over 2}}, z-{\script{3\over 2}}]$ . Cg1 is the centroid of C4–C8/C13 ring.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536809051368/hb5255sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051368/hb5255Isup2.hkl

checkCIF report

Comment top

1,2,4-triazole and its derivatives were reported to exhibit various pharmacological activities such as antimicrobial, analgesic, anti-inflammatory, anticancer and antioxidant properties (Amir et al., 2008; Sztanke et al.., 2008; Kuş et al., 2008; Padmavathi et al., 2008). A few derivatives of triazoles have exhibited antimicrobial activity (Isloor et al., 2009). Some of the present day drugs such as ribavirin (antiviral agent), rizatriptan (anti migraine agent), alprazolam (anxiolytic agent), fluconazole and itraconazole (antifungal agents) are the best examples for potent molecules possessing the triazole nucleus. The amino and mercapto groups of 1,2,4-triazoles serve as readily accessible nucleophilic centers of the preparation of N-bridged heterocycles. Keeping in view of the biological importance, we have synthesized the title compound to study its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The triazole ring (C1/N1/N2/C2/N3) make an dihedral angle of 67.42 (5)° with naphthalene ring (C4-C13). Short intermolecular distances between the centroids of the triazole rings [3.2479 (7) Å] indicate the existence of π···π interactions. The molecular structure is linked via pairs of intermolecular N1—H1N1···S1 and N4—H1N4···S1 interactions, forming R²₂ (8) and R²₂ (10) ring motifs (Bernstein et al., 1995), respectively. Bond lengths and angles are within normal ranges, and comparable to a closely related structure (Fun et al., 2009). In the crystal packing (Fig. 2), the molecules are linked into infinite one-dimensional chains along the direction [0 0 1] via adjacent ring motifs and C12–H12A···S1 interactions (Fig. 2). The crystal strcuture is further consolidated by C–H···π (Table 1) interactions.

Related literature top

For general background to and the pharmacological activity of triazole derivatives, see: Amir et al. (2008); Sztanke et al. (2008); Kuş et al. (2008); Padmavathi et al. (2008); Isloor et al. (2009). For a related structure, see: Fun et al. (2009). For hydrogen-bond motifs, see: Bernstein et al. (1995). For the preparation, see: Suresh (1992). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). Cg1 is the centroid of C4–C8/C13 ring.

Experimental top

2-(1-Naphthyloxy)acetohydrazide (21.6 g, 1.00 mmol) was added slowly to a solution of potassium hydroxide (8.4 g, 1.50 mmol) in ethanol (150 ml). The resulting mixture was stirred well until a clear solution was obtained. Carbon disulphide (11.4 g, 1.50 mmol) was added drop-wise and the contents were stirred vigorously. Further stirring was continued for 24 h. The resulting mixture was diluted with ether (100 ml) and the precipitate formed was collected by filtration, washed with dry ether and dried at 65 /%c under vacuum. It was used for the next step without any purification.

A mixture of the above synthesized potassium dithiocarbazinate (16.5 g, 0.50 mmol), hydrazine hydrate (99 %, 1.00 mmol) and water (2 ml) was heated gently to boil for 30 minutes. Heating was continued until the evacuation of hydrogen sulphide ceased. The reaction mixture was cooled to room temperature, diluted with water (100 ml) and acidified with HCl. The solid mass that separated was collected by filtration, washed with water and dried. Recrystallization was achieved from ethanol. The yield was 9.25 g (68 %), m. p. 470-471 K (Suresh, 1992).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (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, 2009).

Figures top

	Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of (I) viewed along the b axis. Intermolecular interactions are shown in dashed lines.

4-Amino-3-(1-naphthyloxymethyl)-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₃H₁₂N₄OS	F(000) = 568
M_r = 272.33	D_x = 1.445 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5692 reflections
a = 7.0023 (1) Å	θ = 2.9–35.1°
b = 24.0785 (4) Å	µ = 0.26 mm⁻¹
c = 8.0915 (1) Å	T = 100 K
β = 113.404 (1)°	Plate, yellow
V = 1252.02 (3) Å³	0.38 × 0.23 × 0.07 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	5826 independent reflections
Radiation source: fine-focus sealed tube	4223 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
ϕ and ω scans	θ_max = 35.8°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
T_min = 0.908, T_max = 0.983	k = −39→38
24326 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0592P)² + 0.214P] where P = (F_o² + 2F_c²)/3
5826 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₃H₁₂N₄OS	V = 1252.02 (3) Å³
M_r = 272.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0023 (1) Å	µ = 0.26 mm⁻¹
b = 24.0785 (4) Å	T = 100 K
c = 8.0915 (1) Å	0.38 × 0.23 × 0.07 mm
β = 113.404 (1)°

Data collection top

Bruker SMART APEXII CCD diffractometer	5826 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4223 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.983	R_int = 0.045
24326 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.122	All H-atom parameters refined
S = 1.03	Δρ_max = 0.51 e Å⁻³
5826 reflections	Δρ_min = −0.33 e Å⁻³
220 parameters

Special details top

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

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	0.00629 (5)	0.044619 (13)	0.25791 (4)	0.01810 (8)
O1	0.52129 (13)	−0.11362 (4)	0.14188 (11)	0.01666 (16)
N1	0.22651 (15)	−0.04341 (4)	0.46060 (13)	0.01481 (17)
N2	0.38889 (16)	−0.07854 (4)	0.47914 (13)	0.01636 (18)
N3	0.33179 (15)	−0.01814 (4)	0.25913 (12)	0.01411 (17)
N4	0.37675 (18)	0.01243 (5)	0.13172 (14)	0.0193 (2)
C1	0.18602 (17)	−0.00623 (5)	0.32721 (14)	0.01419 (19)
C2	0.44981 (17)	−0.06189 (5)	0.35421 (15)	0.01418 (19)
C3	0.61978 (18)	−0.08762 (5)	0.31417 (15)	0.0162 (2)
C4	0.65096 (17)	−0.13872 (5)	0.07391 (14)	0.01338 (19)
C5	0.86351 (18)	−0.14187 (5)	0.16169 (16)	0.0165 (2)
C6	0.98108 (19)	−0.16981 (5)	0.07908 (17)	0.0195 (2)
C7	0.88492 (19)	−0.19351 (5)	−0.08729 (17)	0.0187 (2)
C8	0.66644 (18)	−0.19040 (5)	−0.18076 (15)	0.01484 (19)
C9	0.5615 (2)	−0.21540 (5)	−0.35253 (16)	0.0185 (2)
C10	0.3499 (2)	−0.21323 (5)	−0.43817 (16)	0.0199 (2)
C11	0.2304 (2)	−0.18580 (5)	−0.35758 (16)	0.0178 (2)
C12	0.32576 (18)	−0.16061 (5)	−0.19258 (15)	0.01452 (19)
C13	0.54499 (17)	−0.16261 (4)	−0.10061 (14)	0.01255 (18)
H3A	0.693 (2)	−0.1148 (6)	0.405 (2)	0.013 (3)*
H3B	0.715 (2)	−0.0602 (6)	0.310 (2)	0.015 (4)*
H5A	0.940 (3)	−0.1254 (7)	0.279 (2)	0.022 (4)*
H6A	1.131 (3)	−0.1723 (7)	0.134 (2)	0.029 (4)*
H7A	0.962 (3)	−0.2110 (7)	−0.143 (2)	0.026 (4)*
H9A	0.647 (3)	−0.2335 (7)	−0.404 (2)	0.031 (5)*
H10A	0.288 (3)	−0.2318 (7)	−0.550 (2)	0.028 (4)*
H11A	0.080 (3)	−0.1865 (7)	−0.414 (2)	0.023 (4)*
H12A	0.240 (3)	−0.1418 (7)	−0.142 (2)	0.022 (4)*
H1N1	0.162 (3)	−0.0455 (7)	0.536 (3)	0.031 (5)*
H1N4	0.284 (3)	0.0023 (8)	0.022 (3)	0.035 (5)*
H2N4	0.354 (3)	0.0475 (8)	0.153 (3)	0.035 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01841 (14)	0.02112 (15)	0.01629 (13)	0.00540 (10)	0.00852 (11)	0.00193 (10)
O1	0.0150 (4)	0.0207 (4)	0.0148 (3)	0.0010 (3)	0.0065 (3)	−0.0072 (3)
N1	0.0161 (4)	0.0159 (4)	0.0151 (4)	0.0006 (3)	0.0090 (4)	−0.0001 (3)
N2	0.0187 (4)	0.0159 (4)	0.0170 (4)	0.0015 (4)	0.0098 (4)	−0.0006 (3)
N3	0.0157 (4)	0.0156 (4)	0.0129 (4)	0.0004 (3)	0.0077 (3)	−0.0001 (3)
N4	0.0248 (5)	0.0216 (5)	0.0153 (4)	0.0013 (4)	0.0122 (4)	0.0031 (4)
C1	0.0144 (5)	0.0157 (5)	0.0133 (4)	−0.0014 (4)	0.0064 (4)	−0.0022 (3)
C2	0.0151 (5)	0.0143 (5)	0.0138 (4)	−0.0005 (4)	0.0064 (4)	−0.0029 (3)
C3	0.0157 (5)	0.0191 (5)	0.0135 (4)	0.0012 (4)	0.0056 (4)	−0.0044 (4)
C4	0.0141 (4)	0.0139 (5)	0.0140 (4)	0.0013 (3)	0.0076 (4)	−0.0015 (3)
C5	0.0148 (5)	0.0188 (5)	0.0156 (5)	0.0000 (4)	0.0057 (4)	−0.0023 (4)
C6	0.0145 (5)	0.0233 (6)	0.0218 (5)	0.0027 (4)	0.0085 (4)	−0.0006 (4)
C7	0.0187 (5)	0.0193 (5)	0.0218 (5)	0.0035 (4)	0.0118 (5)	−0.0007 (4)
C8	0.0187 (5)	0.0130 (5)	0.0159 (4)	0.0008 (4)	0.0100 (4)	0.0001 (4)
C9	0.0259 (6)	0.0157 (5)	0.0172 (5)	−0.0006 (4)	0.0120 (5)	−0.0034 (4)
C10	0.0261 (6)	0.0174 (5)	0.0153 (5)	−0.0032 (4)	0.0072 (5)	−0.0039 (4)
C11	0.0185 (5)	0.0177 (5)	0.0159 (5)	−0.0026 (4)	0.0054 (4)	0.0000 (4)
C12	0.0156 (5)	0.0137 (5)	0.0148 (4)	−0.0003 (4)	0.0066 (4)	−0.0003 (4)
C13	0.0145 (5)	0.0111 (4)	0.0129 (4)	0.0004 (3)	0.0065 (4)	−0.0003 (3)

Geometric parameters (Å, º) top

S1—C1	1.6842 (12)	C5—C6	1.4192 (16)
O1—C4	1.3743 (12)	C5—H5A	0.971 (17)
O1—C3	1.4308 (13)	C6—C7	1.3678 (18)
N1—C1	1.3431 (14)	C6—H6A	0.964 (18)
N1—N2	1.3768 (13)	C7—C8	1.4138 (17)
N1—H1N1	0.894 (19)	C7—H7A	0.931 (17)
N2—C2	1.3066 (14)	C8—C9	1.4223 (16)
N3—C1	1.3691 (13)	C8—C13	1.4246 (15)
N3—C2	1.3710 (15)	C9—C10	1.3648 (19)
N3—N4	1.4005 (13)	C9—H9A	0.964 (17)
N4—H1N4	0.90 (2)	C10—C11	1.4123 (17)
N4—H2N4	0.888 (19)	C10—H10A	0.947 (18)
C2—C3	1.4872 (15)	C11—C12	1.3740 (16)
C3—H3A	0.966 (15)	C11—H11A	0.967 (17)
C3—H3B	0.948 (15)	C12—C13	1.4160 (16)
C4—C5	1.3732 (16)	C12—H12A	0.960 (16)
C4—C13	1.4294 (15)

C4—O1—C3	116.29 (9)	C4—C5—H5A	123.0 (10)
C1—N1—N2	113.50 (9)	C6—C5—H5A	117.3 (10)
C1—N1—H1N1	125.7 (12)	C7—C6—C5	120.69 (11)
N2—N1—H1N1	120.7 (12)	C7—C6—H6A	116.6 (10)
C2—N2—N1	103.67 (9)	C5—C6—H6A	122.6 (10)
C1—N3—C2	108.34 (9)	C6—C7—C8	120.62 (10)
C1—N3—N4	127.42 (10)	C6—C7—H7A	121.0 (11)
C2—N3—N4	123.73 (9)	C8—C7—H7A	118.4 (11)
N3—N4—H1N4	107.3 (12)	C7—C8—C9	121.97 (10)
N3—N4—H2N4	104.3 (12)	C7—C8—C13	119.74 (10)
H1N4—N4—H2N4	109.4 (18)	C9—C8—C13	118.27 (10)
N1—C1—N3	103.33 (9)	C10—C9—C8	121.01 (10)
N1—C1—S1	130.05 (8)	C10—C9—H9A	122.4 (11)
N3—C1—S1	126.60 (9)	C8—C9—H9A	116.6 (11)
N2—C2—N3	111.15 (10)	C9—C10—C11	120.41 (11)
N2—C2—C3	125.18 (11)	C9—C10—H10A	117.4 (10)
N3—C2—C3	123.64 (10)	C11—C10—H10A	122.2 (10)
O1—C3—C2	106.07 (9)	C12—C11—C10	120.45 (11)
O1—C3—H3A	110.6 (9)	C12—C11—H11A	119.1 (10)
C2—C3—H3A	109.9 (8)	C10—C11—H11A	120.4 (10)
O1—C3—H3B	110.0 (9)	C11—C12—C13	120.17 (10)
C2—C3—H3B	110.6 (9)	C11—C12—H12A	118.5 (10)
H3A—C3—H3B	109.6 (13)	C13—C12—H12A	121.4 (10)
C5—C4—O1	124.75 (10)	C12—C13—C8	119.68 (10)
C5—C4—C13	121.29 (9)	C12—C13—C4	122.31 (9)
O1—C4—C13	113.96 (9)	C8—C13—C4	117.98 (10)
C4—C5—C6	119.66 (11)

C1—N1—N2—C2	0.50 (13)	C4—C5—C6—C7	0.18 (19)
N2—N1—C1—N3	−0.61 (12)	C5—C6—C7—C8	0.32 (19)
N2—N1—C1—S1	−179.18 (9)	C6—C7—C8—C9	−178.92 (12)
C2—N3—C1—N1	0.48 (12)	C6—C7—C8—C13	−0.36 (18)
N4—N3—C1—N1	−171.51 (10)	C7—C8—C9—C10	178.15 (11)
C2—N3—C1—S1	179.11 (9)	C13—C8—C9—C10	−0.43 (17)
N4—N3—C1—S1	7.12 (17)	C8—C9—C10—C11	0.18 (18)
N1—N2—C2—N3	−0.17 (12)	C9—C10—C11—C12	0.48 (18)
N1—N2—C2—C3	−178.26 (11)	C10—C11—C12—C13	−0.87 (17)
C1—N3—C2—N2	−0.20 (13)	C11—C12—C13—C8	0.61 (16)
N4—N3—C2—N2	172.15 (10)	C11—C12—C13—C4	−177.82 (11)
C1—N3—C2—C3	177.92 (10)	C7—C8—C13—C12	−178.58 (11)
N4—N3—C2—C3	−9.73 (17)	C9—C8—C13—C12	0.03 (16)
C4—O1—C3—C2	177.76 (9)	C7—C8—C13—C4	−0.08 (16)
N2—C2—C3—O1	110.95 (12)	C9—C8—C13—C4	178.53 (10)
N3—C2—C3—O1	−66.91 (14)	C5—C4—C13—C12	179.03 (11)
C3—O1—C4—C5	2.21 (16)	O1—C4—C13—C12	−0.50 (15)
C3—O1—C4—C13	−178.28 (9)	C5—C4—C13—C8	0.57 (16)
O1—C4—C5—C6	178.85 (11)	O1—C4—C13—C8	−178.96 (9)
C13—C4—C5—C6	−0.63 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S1ⁱ	0.89 (2)	2.39 (2)	3.2857 (11)	176.2 (14)
N4—H1N4···S1ⁱⁱ	0.90 (2)	2.62 (2)	3.5075 (12)	167.3 (19)
C12—H12A···S1ⁱⁱ	0.96 (2)	2.836 (18)	3.5368 (13)	130.3 (12)
C9—H9A···Cg1ⁱⁱⁱ	0.964 (17)	2.794 (18)	3.6345 (14)	146.8 (14)

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

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₄OS
M_r	272.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.0023 (1), 24.0785 (4), 8.0915 (1)
β (°)	113.404 (1)
V (Å³)	1252.02 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.38 × 0.23 × 0.07

Data collection
Diffractometer	Bruker SMART APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.908, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	24326, 5826, 4223
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.823

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.122, 1.03
No. of reflections	5826
No. of parameters	220
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.33

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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···S1ⁱ	0.89 (2)	2.39 (2)	3.2857 (11)	176.2 (14)
N4—H1N4···S1ⁱⁱ	0.90 (2)	2.62 (2)	3.5075 (12)	167.3 (19)
C12—H12A···S1ⁱⁱ	0.96 (2)	2.836 (18)	3.5368 (13)	130.3 (12)
C9—H9A···Cg1ⁱⁱⁱ	0.964 (17)	2.794 (18)	3.6345 (14)	146.8 (14)

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Golden Goose Grant (1001/PFIZIK/811012). CKQ thanks USM for a Research Fellowship. AMI is grateful to the Head of the Department of Chemistry and Director, NITK, Surathkal, India, for providing research facilities.

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