3-(Adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

El-Emam, A.A.; El-Brollosy, N.R.; Ghabbour, H.A.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536812014407

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1347

doi:10.1107/S1600536812014407

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3-(Adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

Ali A. El-Emam,^a Nasser R. El-Brollosy,^a Hazem A. Ghabbour,^a Ching Kheng Quah ^b ‡ and Hoong-Kun Fun ^b ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 28 March 2012; accepted 3 April 2012; online 13 April 2012)

In the title compound, C₁₄H₂₁N₃S, the 1,2,4-triazole ring is nearly planar, with a maximum deviation of 0.003 (4) Å. In the crystal, molecules are linked into inversion dimers by pairs of N—H⋯S hydrogen bonds.

Related literature

For the biological activity of adamantane derivatives, see: Al-Omar et al. (2010 ); Al-Deeb et al. (2006 ); El-Emam et al. (2004 ); Kadi et al. (2007 , 2010 ); Vernier et al. (1969 ). For the synthesis of the title compound, see: El-Emam & Ibrahim (1991 ). For related structures of adamantane derivatives, see: Almutairi et al. (2012 ); Al-Tamimi et al. (2010 ); Rouchal et al. (2010 ); Wang et al. (2011 ); Al-Abdullah et al. (2012 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₂₁N₃S
M_r = 263.40
Monoclinic, P 2₁ /c
a = 13.8329 (7) Å
b = 7.3107 (4) Å
c = 17.5302 (12) Å
β = 128.157 (4)°
V = 1393.99 (16) Å³
Z = 4
Cu Kα radiation
μ = 1.94 mm⁻¹
T = 296 K
0.58 × 0.12 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.228, T_max = 0.906
8009 measured reflections
2448 independent reflections
1632 reflections with I > 2σ(I)
R_int = 0.093

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.167
S = 1.13
2448 reflections
168 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯S1ⁱ	0.88 (4)	2.47 (4)	3.338 (4)	170 (4)
Symmetry code: (i) -x, -y+2, -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/S1600536812014407/is5108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014407/is5108Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014407/is5108Isup3.cml

checkCIF report

Comment top

Derivatives of adamantane have long been known for their diverse biological activities including antiviral activity against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam et al. 2004). Moreover, adamantane derivatives were recently reported to exhibit marked antibacterial activity (Kadi et al., 2007, 2010). In an earlier publication, we reported the synthesis and potent anti-inflammatory and analgesic activities of a series of 5-(1-adamantyl)-4-substituted-4H-1,2,4-triazole-3-thiols and related derivatives including the title compound (El-Emam & Ibrahim, 1991).

In the title molecule (Fig. 1), the 1,2,4-triazole ring (N1–N3/C1/C2) is nearly planar with a maximum deviation of 0.003 (4)) Å at atom C1. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to related structures (Almutairi et al., 2012; Al-Tamimi et al., 2010; Rouchal et al., 2010; Wang et al., 2011; Al-Abdullah et al., 2012).

In the crystal (Fig. 2), molecules are linked into inversion dimers by pairs of intermolecular N2—H2A···S1 hydrogen bonds (Table 1).

Related literature top

For the biological activity of adamantane derivatives, see: Al-Omar et al. (2010); Al-Deeb et al. (2006); El-Emam et al. (2004); Kadi et al. (2007, 2010); Vernier et al. (1969). For the synthesis of the title compound, see: El-Emam & Ibrahim (1991). For related structures of adamantane derivatives, see: Almutairi et al. (2012); Al-Tamimi et al. (2010); Rouchal et al. (2010); Wang et al. (2011); Al-Abdullah et al. (2012). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of adamantane-1-carbohydrazide (1.94 g, 0.01 mol), ethyl isothiocyanate (0.87 g, 0.01 mol), in ethanol (10 ml) was heated under reflux with stirring for one hour and the solvent was distilled off in vacuo. Aqueous sodium hydroxide solution (10%, 15 ml) was added to the residue and the mixture was heated under reflux for 2 h, then filtered hot. On cooling, the mixture was acidified with hydrochloric acid and the precipitated crude product was filtered, washed with water, dried and crystallized from aqueous ethanol to yield 2.24 g (85%) of the title compound (C₁₄H₂₁N₃S) as colorless crystals. M.p.: 210-212 °C. ¹H NMR (CDCl₃, 500.13 MHz): δ 1.36 (t, 3H, CH₃CH₂, J = 7.0 Hz), 1.73 (s, 6H, Adamantane-H), 1.99 (m, 6H, Adamantane-H), 2.06 (s, 3H, Adamantane-H), 4.19 (q, 2H, CH₃CH₂), 11.60 (br. s, 1H, NH). ¹³C NMR (CDCl₃, 125.76 MHz): δ 13.99 (CH₃), 27.91, 35.48, 36.27, 39.75 (Adamantane-C), 41.17 (CH₂), 158.04 (C=N), 167.25 (C=S).

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, showing 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

3-(Adamantan-1-yl)-4-ethyl-1H-1,2,4-triazole-5(4H)-thione top

Crystal data top

C₁₄H₂₁N₃S	F(000) = 568
M_r = 263.40	D_x = 1.255 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 592 reflections
a = 13.8329 (7) Å	θ = 4.1–66.5°
b = 7.3107 (4) Å	µ = 1.94 mm⁻¹
c = 17.5302 (12) Å	T = 296 K
β = 128.157 (4)°	Needle, colourless
V = 1393.99 (16) Å³	0.58 × 0.12 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2448 independent reflections
Radiation source: fine-focus sealed tube	1632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
ϕ and ω scans	θ_max = 67.5°, θ_min = 4.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
T_min = 0.228, T_max = 0.906	k = −8→6
8009 measured reflections	l = −20→19

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0553P)² + 1.0409P] where P = (F_o² + 2F_c²)/3
2448 reflections	(Δ/σ)_max = 0.001
168 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₂₁N₃S	V = 1393.99 (16) Å³
M_r = 263.40	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.8329 (7) Å	µ = 1.94 mm⁻¹
b = 7.3107 (4) Å	T = 296 K
c = 17.5302 (12) Å	0.58 × 0.12 × 0.05 mm
β = 128.157 (4)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2448 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1632 reflections with I > 2σ(I)
T_min = 0.228, T_max = 0.906	R_int = 0.093
8009 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	Δρ_max = 0.19 e Å⁻³
2448 reflections	Δρ_min = −0.26 e Å⁻³
168 parameters

Special details top

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	−0.10923 (11)	0.88672 (13)	0.05119 (8)	0.0602 (4)
N1	0.0606 (3)	0.6128 (4)	0.1520 (2)	0.0452 (7)
N2	0.0957 (4)	0.7839 (4)	0.0738 (3)	0.0591 (10)
N3	0.1903 (3)	0.6609 (4)	0.1203 (2)	0.0571 (9)
C1	0.0152 (4)	0.7606 (4)	0.0913 (3)	0.0490 (10)
C2	0.1677 (4)	0.5561 (5)	0.1684 (3)	0.0479 (9)
C3	0.2544 (4)	0.4078 (5)	0.2347 (3)	0.0505 (9)
C4	0.3537 (4)	0.3859 (5)	0.2218 (4)	0.0733 (13)
H4A	0.3954	0.5018	0.2345	0.088*
H4B	0.3158	0.3509	0.1554	0.088*
C5	0.4475 (5)	0.2398 (6)	0.2914 (5)	0.0821 (15)
H5A	0.5104	0.2284	0.2822	0.099*
C6	0.5089 (5)	0.2972 (7)	0.3961 (5)	0.0953 (18)
H6A	0.5695	0.2068	0.4406	0.114*
H6B	0.5504	0.4136	0.4096	0.114*
C7	0.4113 (4)	0.3141 (6)	0.4098 (3)	0.0710 (12)
H7A	0.4502	0.3481	0.4771	0.085*
C8	0.3435 (4)	0.1329 (5)	0.3865 (3)	0.0660 (12)
H8A	0.2810	0.1455	0.3951	0.079*
H8B	0.4009	0.0391	0.4307	0.079*
C9	0.2836 (4)	0.0760 (5)	0.2820 (3)	0.0587 (11)
H9A	0.2415	−0.0414	0.2682	0.070*
C10	0.1908 (4)	0.2214 (5)	0.2139 (3)	0.0524 (10)
H10A	0.1279	0.2312	0.2223	0.063*
H10B	0.1512	0.1862	0.1473	0.063*
C11	0.3813 (5)	0.0576 (6)	0.2681 (4)	0.0781 (14)
H11A	0.3433	0.0231	0.2016	0.094*
H11B	0.4397	−0.0369	0.3106	0.094*
C12	0.3189 (4)	0.4605 (5)	0.3421 (3)	0.0595 (11)
H12A	0.3607	0.5768	0.3564	0.071*
H12B	0.2579	0.4739	0.3523	0.071*
C13	−0.0034 (4)	0.5359 (5)	0.1871 (3)	0.0486 (9)
H13A	−0.0375	0.6350	0.2006	0.058*
H13B	0.0553	0.4710	0.2474	0.058*
C14	−0.1058 (4)	0.4064 (5)	0.1148 (3)	0.0577 (10)
H14A	−0.1485	0.3664	0.1389	0.087*
H14B	−0.0717	0.3024	0.1056	0.087*
H14C	−0.1622	0.4682	0.0540	0.087*
H1N2	0.089 (3)	0.868 (5)	0.035 (3)	0.063 (12)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0812 (8)	0.0444 (6)	0.0664 (7)	0.0174 (5)	0.0513 (6)	0.0157 (4)
N1	0.060 (2)	0.0367 (15)	0.0490 (17)	0.0075 (14)	0.0389 (16)	0.0066 (12)
N2	0.088 (3)	0.0436 (19)	0.069 (2)	0.0136 (17)	0.060 (2)	0.0182 (16)
N3	0.076 (2)	0.0419 (17)	0.074 (2)	0.0115 (16)	0.057 (2)	0.0146 (15)
C1	0.071 (3)	0.0329 (18)	0.048 (2)	0.0057 (17)	0.039 (2)	0.0031 (15)
C2	0.064 (3)	0.0383 (19)	0.053 (2)	0.0010 (17)	0.042 (2)	0.0002 (15)
C3	0.059 (3)	0.040 (2)	0.064 (2)	0.0053 (17)	0.043 (2)	0.0074 (16)
C4	0.086 (3)	0.051 (2)	0.120 (4)	0.012 (2)	0.082 (3)	0.020 (2)
C5	0.074 (3)	0.062 (3)	0.140 (5)	0.022 (2)	0.080 (4)	0.029 (3)
C6	0.061 (3)	0.071 (3)	0.127 (5)	0.005 (3)	0.045 (3)	0.025 (3)
C7	0.055 (3)	0.064 (3)	0.068 (3)	−0.004 (2)	0.025 (2)	0.005 (2)
C8	0.053 (3)	0.057 (3)	0.070 (3)	0.007 (2)	0.029 (2)	0.023 (2)
C9	0.061 (3)	0.037 (2)	0.078 (3)	0.0047 (18)	0.043 (2)	0.0093 (18)
C10	0.062 (3)	0.044 (2)	0.055 (2)	0.0045 (18)	0.038 (2)	0.0048 (16)
C11	0.081 (3)	0.052 (3)	0.118 (4)	0.022 (2)	0.070 (3)	0.020 (3)
C12	0.060 (3)	0.045 (2)	0.063 (3)	−0.0037 (18)	0.032 (2)	0.0001 (18)
C13	0.065 (3)	0.043 (2)	0.052 (2)	0.0083 (18)	0.043 (2)	0.0071 (16)
C14	0.060 (3)	0.049 (2)	0.067 (3)	−0.0003 (19)	0.041 (2)	−0.0006 (18)

Geometric parameters (Å, º) top

S1—C1	1.677 (4)	C7—C12	1.521 (5)
N1—C1	1.367 (4)	C7—C8	1.526 (5)
N1—C2	1.386 (5)	C7—H7A	0.9800
N1—C13	1.468 (4)	C8—C9	1.530 (6)
N2—C1	1.337 (5)	C8—H8A	0.9700
N2—N3	1.366 (4)	C8—H8B	0.9700
N2—H1N2	0.87 (4)	C9—C10	1.520 (5)
N3—C2	1.312 (4)	C9—C11	1.522 (6)
C2—C3	1.497 (5)	C9—H9A	0.9800
C3—C4	1.533 (5)	C10—H10A	0.9700
C3—C10	1.539 (5)	C10—H10B	0.9700
C3—C12	1.553 (5)	C11—H11A	0.9700
C4—C5	1.535 (6)	C11—H11B	0.9700
C4—H4A	0.9700	C12—H12A	0.9700
C4—H4B	0.9700	C12—H12B	0.9700
C5—C11	1.522 (6)	C13—C14	1.514 (5)
C5—C6	1.530 (7)	C13—H13A	0.9700
C5—H5A	0.9800	C13—H13B	0.9700
C6—C7	1.515 (7)	C14—H14A	0.9600
C6—H6A	0.9700	C14—H14B	0.9600
C6—H6B	0.9700	C14—H14C	0.9600

C1—N1—C2	108.5 (3)	C7—C8—C9	110.2 (3)
C1—N1—C13	121.5 (3)	C7—C8—H8A	109.6
C2—N1—C13	130.0 (3)	C9—C8—H8A	109.6
C1—N2—N3	113.9 (3)	C7—C8—H8B	109.6
C1—N2—H1N2	124 (3)	C9—C8—H8B	109.6
N3—N2—H1N2	122 (3)	H8A—C8—H8B	108.1
C2—N3—N2	104.3 (3)	C10—C9—C11	109.8 (3)
N2—C1—N1	103.4 (3)	C10—C9—C8	108.7 (3)
N2—C1—S1	128.2 (3)	C11—C9—C8	109.8 (4)
N1—C1—S1	128.3 (3)	C10—C9—H9A	109.5
N3—C2—N1	109.9 (3)	C11—C9—H9A	109.5
N3—C2—C3	121.8 (3)	C8—C9—H9A	109.5
N1—C2—C3	128.2 (3)	C9—C10—C3	110.6 (3)
C2—C3—C4	108.8 (3)	C9—C10—H10A	109.5
C2—C3—C10	113.0 (3)	C3—C10—H10A	109.5
C4—C3—C10	107.9 (3)	C9—C10—H10B	109.5
C2—C3—C12	110.2 (3)	C3—C10—H10B	109.5
C4—C3—C12	108.0 (3)	H10A—C10—H10B	108.1
C10—C3—C12	108.8 (3)	C9—C11—C5	109.0 (3)
C3—C4—C5	110.5 (3)	C9—C11—H11A	109.9
C3—C4—H4A	109.6	C5—C11—H11A	109.9
C5—C4—H4A	109.6	C9—C11—H11B	109.9
C3—C4—H4B	109.6	C5—C11—H11B	109.9
C5—C4—H4B	109.6	H11A—C11—H11B	108.3
H4A—C4—H4B	108.1	C7—C12—C3	110.3 (3)
C11—C5—C6	111.0 (4)	C7—C12—H12A	109.6
C11—C5—C4	108.8 (4)	C3—C12—H12A	109.6
C6—C5—C4	109.4 (4)	C7—C12—H12B	109.6
C11—C5—H5A	109.2	C3—C12—H12B	109.6
C6—C5—H5A	109.2	H12A—C12—H12B	108.1
C4—C5—H5A	109.2	N1—C13—C14	112.5 (3)
C7—C6—C5	108.9 (4)	N1—C13—H13A	109.1
C7—C6—H6A	109.9	C14—C13—H13A	109.1
C5—C6—H6A	109.9	N1—C13—H13B	109.1
C7—C6—H6B	109.9	C14—C13—H13B	109.1
C5—C6—H6B	109.9	H13A—C13—H13B	107.8
H6A—C6—H6B	108.3	C13—C14—H14A	109.5
C6—C7—C12	109.6 (4)	C13—C14—H14B	109.5
C6—C7—C8	110.4 (4)	H14A—C14—H14B	109.5
C12—C7—C8	108.7 (3)	C13—C14—H14C	109.5
C6—C7—H7A	109.4	H14A—C14—H14C	109.5
C12—C7—H7A	109.4	H14B—C14—H14C	109.5
C8—C7—H7A	109.4

C1—N2—N3—C2	0.3 (4)	C11—C5—C6—C7	−59.4 (5)
N3—N2—C1—N1	−0.6 (4)	C4—C5—C6—C7	60.7 (5)
N3—N2—C1—S1	177.7 (3)	C5—C6—C7—C12	−61.3 (5)
C2—N1—C1—N2	0.6 (4)	C5—C6—C7—C8	58.3 (5)
C13—N1—C1—N2	−178.0 (3)	C6—C7—C8—C9	−58.9 (5)
C2—N1—C1—S1	−177.7 (3)	C12—C7—C8—C9	61.4 (5)
C13—N1—C1—S1	3.8 (5)	C7—C8—C9—C10	−61.4 (4)
N2—N3—C2—N1	0.1 (4)	C7—C8—C9—C11	58.8 (4)
N2—N3—C2—C3	−176.4 (3)	C11—C9—C10—C3	−60.1 (4)
C1—N1—C2—N3	−0.4 (4)	C8—C9—C10—C3	60.0 (4)
C13—N1—C2—N3	177.9 (3)	C2—C3—C10—C9	178.9 (3)
C1—N1—C2—C3	175.8 (3)	C4—C3—C10—C9	58.6 (4)
C13—N1—C2—C3	−5.9 (6)	C12—C3—C10—C9	−58.3 (4)
N3—C2—C3—C4	−8.8 (5)	C10—C9—C11—C5	60.7 (5)
N1—C2—C3—C4	175.4 (4)	C8—C9—C11—C5	−58.8 (5)
N3—C2—C3—C10	−128.6 (4)	C6—C5—C11—C9	59.8 (5)
N1—C2—C3—C10	55.6 (5)	C4—C5—C11—C9	−60.7 (5)
N3—C2—C3—C12	109.5 (4)	C6—C7—C12—C3	61.0 (5)
N1—C2—C3—C12	−66.3 (5)	C8—C7—C12—C3	−59.7 (5)
C2—C3—C4—C5	177.9 (4)	C2—C3—C12—C7	−177.4 (3)
C10—C3—C4—C5	−59.2 (5)	C4—C3—C12—C7	−58.7 (4)
C12—C3—C4—C5	58.2 (5)	C10—C3—C12—C7	58.2 (4)
C3—C4—C5—C11	61.2 (5)	C1—N1—C13—C14	82.7 (4)
C3—C4—C5—C6	−60.3 (5)	C2—N1—C13—C14	−95.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···S1ⁱ	0.88 (4)	2.47 (4)	3.338 (4)	170 (4)

Symmetry code: (i) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₄H₂₁N₃S
M_r	263.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	13.8329 (7), 7.3107 (4), 17.5302 (12)
β (°)	128.157 (4)
V (Å³)	1393.99 (16)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.94
Crystal size (mm)	0.58 × 0.12 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.228, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	8009, 2448, 1632
R_int	0.093
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.167, 1.13
No. of reflections	2448
No. of parameters	168
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008), 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
N2—H1N2···S1ⁱ	0.88 (4)	2.47 (4)	3.338 (4)	170 (4)

Symmetry code: (i) −x, −y+2, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated. HKF and CKQ thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160).

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