2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfan­yl}-N,N-dimethyl­ethanamine

El-Emam, A.A.; Lahsasni, S.; Asiri, H.H.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S160053681201464X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1356

doi:10.1107/S160053681201464X

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2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N,N-dimethylethanamine

Ali A. El-Emam,^a Siham Lahsasni,^b Hanadi H. Asiri,^a Ching Kheng Quah ^c ‡ and Hoong-Kun Fun ^c ^*§

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

(Received 28 March 2012; accepted 4 April 2012; online 13 April 2012)

In the title compound, C₁₇H₂₈N₄S, the 1,2,4-triazole ring is nearly planar [maximum deviation = 0.005 (2) Å]. There are no significant hydrogen bonds observed in the crystal structure. The crystal studied was a non-merohedral twin, the refined ratio of twin components being 0.281 (3):0.719 (3).

Related literature

For the biological activity of adamantyl 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 structures of related adamantyl-1,2,4-triazoles, see: Almutairi et al. (2012 ); Al-Tamimi et al. (2010 ); Al-Abdullah et al. (2012 ). For the structures of substituted sulfanyl-1,2,4-triazoles, see: Fun et al. (2011 ); Wang et al. (2011 ). For standard bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₇H₂₈N₄S
M_r = 320.49
Monoclinic, P 2₁ /c
a = 12.5133 (7) Å
b = 10.3779 (5) Å
c = 14.3044 (8) Å
β = 106.766 (3)°
V = 1778.63 (16) Å³
Z = 4
Cu Kα radiation
μ = 1.62 mm⁻¹
T = 296 K
0.64 × 0.59 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.204, T_max = 0.923
3267 measured reflections
3267 independent reflections
2846 reflections with I > 2σ(I)

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.184
S = 1.13
3267 reflections
203 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.37 e Å⁻³

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/S160053681201464X/rz2734sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201464X/rz2734Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681201464X/rz2734Isup3.cml

checkCIF report

Comment top

Considerable attention has been devoted to adamantane derivatives which have long been known for their diverse biological properties as antiviral against the influenza (Vernier et al., 1969) and HIV viruses (El-Emam, Al-Deeb, Al-Omar & Lehmann, 2004). Moreover, adamantane derivatives were recently reported to exhibit marked antibacterial activity (Kadi et al., 2007, 2010). In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives, we synthesized the title compound as a potential chemotherapeutic agent.

In the title molecule, Fig. 1, the 1,2,4-triazole ring (N1-N3/C11/C12) is nearly planar with a maximum deviation of 0.005 (2) Å at atom N2. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Almutairi et al., 2012; Al-Tamimi et al., 2010; Al-Abdullah et al., 2012; Fun et al., 2011; Wang et al., 2011). The crystal studied was a non-merohedral twin, the refined ratio of twin components being 0.281 (3):0.719 (3). There are no significant hydrogen bonds observed in this compound.

Related literature top

For the biological activity of adamantyl 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 structures of related adamantyl-1,2,4-triazoles, see: Almutairi et al. (2012); Al-Tamimi et al. (2010); Al-Abdullah et al. (2012). For the structures of substituted sulfanyl-1,2,4-triazoles, see: Fun et al. (2011); Wang et al. (2011). For standard bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 3-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazole-5-thiol (2.49 g, 0.01 mol), potassium hydroxide (1.12 g, 0.02 mol) and 2-dimethylaminoethyl chloride hydrochloride (1.44 g, 0.01 mol) in ethanol (15 ml) was heated under reflux with stirring for 3 h and the solvent was distilled off in vacuo. The obtained residue was washed with water and purified by column chromatography on silica gel column using CHCl₃:MeOH (9:1 v/v) as eluent to yield 2.02 g (63%) of the title compound as colorless powder. M.p. 133-135°C. Single crystals suitable for X-ray diffraction were obtained by crystallization from aqueous ethanol. ¹H NMR (CDCl₃, 500.13 MHz): δ 1.69-1.75 (m, 6H, adamantane-H), 2.04-2.85 (m, 9H, adamantane-H), 2.21 (s, 6H, 2xCH₃), 2.62 (t, 2H, CH₂N, J = 6.5 Hz), 3.28 (t, 2H, SCH₂, J = 6.5 Hz), 3.59 (s, 3H, CH₃). ¹³C NMR (CDCl₃, 125.76 MHz): δ 28.07, 34.98, 36.50, 49.56 (adamantane-C), 31.05 (CH₃), 32.33 (SCH₂), 45.21 (2xCH₃), 58.24 (CH₂N), 152.16, 161.21 (triazole C).

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.

2-{[5-(Adamantan-1-yl)-4-methyl-4H-1,2,4-triazol-3-yl]sulfanyl}- N,N-dimethylethanamine top

Crystal data top

C₁₇H₂₈N₄S	F(000) = 696
M_r = 320.49	D_x = 1.197 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3932 reflections
a = 12.5133 (7) Å	θ = 7.7–69.2°
b = 10.3779 (5) Å	µ = 1.62 mm⁻¹
c = 14.3044 (8) Å	T = 296 K
β = 106.766 (3)°	Plate, colourless
V = 1778.63 (16) Å³	0.64 × 0.59 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3267 independent reflections
Radiation source: fine-focus sealed tube	2846 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ϕ and ω scans	θ_max = 69.8°, θ_min = 7.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→14
T_min = 0.204, T_max = 0.923	k = −12→12
3267 measured reflections	l = 0→16

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.13	w = 1/[σ²(F_o²) + (0.P)² + 1.1111P] where P = (F_o² + 2F_c²)/3
3267 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₇H₂₈N₄S	V = 1778.63 (16) Å³
M_r = 320.49	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 12.5133 (7) Å	µ = 1.62 mm⁻¹
b = 10.3779 (5) Å	T = 296 K
c = 14.3044 (8) Å	0.64 × 0.59 × 0.05 mm
β = 106.766 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3267 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	2846 reflections with I > 2σ(I)
T_min = 0.204, T_max = 0.923	R_int = 0.000
3267 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.13	Δρ_max = 0.32 e Å⁻³
3267 reflections	Δρ_min = −0.37 e Å⁻³
203 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	0.59451 (7)	0.30472 (8)	0.05471 (7)	0.0589 (3)
N1	0.4306 (2)	0.2967 (2)	0.14471 (19)	0.0478 (6)
N4	0.7649 (3)	0.2967 (3)	−0.0644 (2)	0.0630 (7)
C9	0.2838 (2)	0.2248 (3)	0.2293 (2)	0.0476 (7)
C10	0.3344 (3)	0.2856 (4)	0.3307 (3)	0.0672 (9)
H10A	0.3944	0.2315	0.3689	0.081*
H10B	0.3653	0.3694	0.3234	0.081*
C6	0.2449 (4)	0.3001 (5)	0.3838 (3)	0.0814 (12)
H6A	0.2779	0.3402	0.4477	0.098*
C5	0.1995 (4)	0.1692 (5)	0.3976 (3)	0.0893 (14)
H5A	0.1441	0.1778	0.4328	0.107*
H5B	0.2594	0.1149	0.4359	0.107*
C4	0.1465 (4)	0.1071 (4)	0.2985 (3)	0.0765 (11)
H4A	0.1169	0.0222	0.3077	0.092*
C3	0.0526 (3)	0.1919 (5)	0.2391 (3)	0.0817 (13)
H3A	0.0183	0.1524	0.1761	0.098*
H3B	−0.0041	0.2011	0.2728	0.098*
C13	0.6508 (4)	0.1620 (4)	0.0134 (4)	0.0803 (12)
H13A	0.6560	0.0927	0.0600	0.096*
H13B	0.6015	0.1344	−0.0490	0.096*
C2	0.0985 (3)	0.3229 (4)	0.2249 (3)	0.0757 (11)
H2A	0.0375	0.3775	0.1869	0.091*
C7	0.1513 (4)	0.3853 (5)	0.3230 (4)	0.0861 (13)
H7A	0.0954	0.3977	0.3571	0.103*
H7B	0.1810	0.4691	0.3136	0.103*
C1	0.1858 (3)	0.3084 (4)	0.1699 (3)	0.0653 (9)
H1A	0.2132	0.3927	0.1586	0.078*
H1B	0.1520	0.2684	0.1069	0.078*
C8	0.2350 (3)	0.0923 (3)	0.2444 (3)	0.0666 (9)
H8A	0.2018	0.0521	0.1814	0.080*
H8B	0.2944	0.0367	0.2817	0.080*
C11	0.3702 (2)	0.2040 (3)	0.1772 (2)	0.0477 (7)
N2	0.4021 (2)	0.0897 (2)	0.1572 (2)	0.0577 (7)
N3	0.4859 (3)	0.1046 (3)	0.1120 (2)	0.0599 (7)
C12	0.5001 (3)	0.2289 (3)	0.1054 (2)	0.0516 (7)
C14	0.7641 (4)	0.1909 (5)	0.0031 (4)	0.0874 (14)
H14A	0.8139	0.2124	0.0669	0.105*
H14B	0.7930	0.1140	−0.0196	0.105*
C16	0.7117 (7)	0.2636 (6)	−0.1633 (5)	0.126 (2)
H16A	0.7180	0.3341	−0.2048	0.189*
H16B	0.6342	0.2457	−0.1713	0.189*
H16C	0.7468	0.1886	−0.1805	0.189*
C17	0.4269 (3)	0.4366 (3)	0.1495 (3)	0.0633 (9)
H17A	0.4899	0.4723	0.1330	0.095*
H17B	0.4292	0.4626	0.2145	0.095*
H17C	0.3593	0.4674	0.1043	0.095*
C15	0.8793 (5)	0.3349 (7)	−0.0500 (6)	0.120 (2)
H15A	0.8822	0.4023	−0.0951	0.181*
H15B	0.9217	0.2623	−0.0608	0.181*
H15C	0.9101	0.3655	0.0156	0.181*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0605 (5)	0.0553 (5)	0.0668 (6)	−0.0051 (3)	0.0278 (4)	−0.0023 (4)
N1	0.0524 (14)	0.0418 (13)	0.0497 (15)	0.0000 (10)	0.0156 (11)	0.0003 (10)
N4	0.0598 (17)	0.0665 (18)	0.0661 (19)	0.0050 (13)	0.0236 (14)	0.0030 (14)
C9	0.0478 (15)	0.0505 (16)	0.0430 (16)	0.0012 (12)	0.0105 (13)	−0.0010 (12)
C10	0.060 (2)	0.084 (2)	0.051 (2)	−0.0009 (18)	0.0042 (16)	−0.0097 (17)
C6	0.076 (3)	0.113 (4)	0.054 (2)	−0.003 (2)	0.0162 (19)	−0.021 (2)
C5	0.082 (3)	0.133 (4)	0.059 (3)	0.012 (3)	0.031 (2)	0.017 (2)
C4	0.079 (3)	0.078 (3)	0.083 (3)	−0.011 (2)	0.039 (2)	0.003 (2)
C3	0.056 (2)	0.123 (4)	0.070 (3)	−0.011 (2)	0.0232 (19)	−0.009 (2)
C13	0.081 (3)	0.064 (2)	0.114 (4)	0.0078 (19)	0.056 (3)	0.006 (2)
C2	0.057 (2)	0.095 (3)	0.073 (3)	0.0195 (19)	0.0154 (18)	0.007 (2)
C7	0.085 (3)	0.092 (3)	0.091 (3)	0.009 (2)	0.042 (3)	−0.018 (2)
C1	0.059 (2)	0.080 (2)	0.055 (2)	0.0125 (16)	0.0139 (16)	0.0096 (17)
C8	0.070 (2)	0.063 (2)	0.072 (2)	−0.0051 (16)	0.0289 (18)	0.0026 (17)
C11	0.0505 (16)	0.0440 (15)	0.0476 (17)	0.0002 (12)	0.0126 (13)	0.0023 (12)
N2	0.0657 (16)	0.0454 (14)	0.0686 (18)	0.0029 (12)	0.0299 (14)	0.0032 (12)
N3	0.0682 (17)	0.0466 (15)	0.0727 (19)	0.0041 (12)	0.0327 (15)	0.0027 (12)
C12	0.0531 (17)	0.0499 (17)	0.0499 (18)	0.0020 (13)	0.0118 (14)	0.0008 (13)
C14	0.080 (3)	0.094 (3)	0.096 (3)	0.024 (2)	0.038 (3)	0.024 (3)
C16	0.181 (6)	0.097 (4)	0.082 (4)	0.030 (4)	0.008 (4)	−0.013 (3)
C17	0.069 (2)	0.0442 (17)	0.080 (2)	−0.0017 (15)	0.0273 (18)	−0.0028 (15)
C15	0.082 (3)	0.137 (5)	0.151 (6)	0.003 (3)	0.047 (4)	0.032 (4)

Geometric parameters (Å, º) top

S1—C12	1.742 (3)	C13—C14	1.498 (6)
S1—C13	1.811 (4)	C13—H13A	0.9700
N1—C12	1.361 (4)	C13—H13B	0.9700
N1—C11	1.384 (4)	C2—C7	1.513 (7)
N1—C17	1.455 (4)	C2—C1	1.527 (5)
N4—C16	1.421 (7)	C2—H2A	0.9800
N4—C15	1.441 (6)	C7—H7A	0.9700
N4—C14	1.464 (5)	C7—H7B	0.9700
C9—C11	1.495 (4)	C1—H1A	0.9700
C9—C10	1.539 (5)	C1—H1B	0.9700
C9—C1	1.542 (4)	C8—H8A	0.9700
C9—C8	1.546 (5)	C8—H8B	0.9700
C10—C6	1.531 (6)	C11—N2	1.310 (4)
C10—H10A	0.9700	N2—N3	1.390 (4)
C10—H10B	0.9700	N3—C12	1.309 (4)
C6—C5	1.508 (7)	C14—H14A	0.9700
C6—C7	1.524 (7)	C14—H14B	0.9700
C6—H6A	0.9800	C16—H16A	0.9600
C5—C4	1.524 (7)	C16—H16B	0.9600
C5—H5A	0.9700	C16—H16C	0.9600
C5—H5B	0.9700	C17—H17A	0.9600
C4—C3	1.517 (7)	C17—H17B	0.9600
C4—C8	1.531 (5)	C17—H17C	0.9600
C4—H4A	0.9800	C15—H15A	0.9600
C3—C2	1.513 (7)	C15—H15B	0.9600
C3—H3A	0.9700	C15—H15C	0.9600
C3—H3B	0.9700

C12—S1—C13	98.05 (17)	C7—C2—H2A	109.2
C12—N1—C11	104.8 (2)	C1—C2—H2A	109.2
C12—N1—C17	124.6 (3)	C2—C7—C6	109.8 (4)
C11—N1—C17	130.5 (3)	C2—C7—H7A	109.7
C16—N4—C15	111.7 (5)	C6—C7—H7A	109.7
C16—N4—C14	112.6 (4)	C2—C7—H7B	109.7
C15—N4—C14	107.9 (4)	C6—C7—H7B	109.7
C11—C9—C10	111.7 (3)	H7A—C7—H7B	108.2
C11—C9—C1	112.4 (3)	C2—C1—C9	110.2 (3)
C10—C9—C1	109.5 (3)	C2—C1—H1A	109.6
C11—C9—C8	108.2 (3)	C9—C1—H1A	109.6
C10—C9—C8	107.7 (3)	C2—C1—H1B	109.6
C1—C9—C8	107.1 (3)	C9—C1—H1B	109.6
C6—C10—C9	110.3 (3)	H1A—C1—H1B	108.1
C6—C10—H10A	109.6	C4—C8—C9	110.7 (3)
C9—C10—H10A	109.6	C4—C8—H8A	109.5
C6—C10—H10B	109.6	C9—C8—H8A	109.5
C9—C10—H10B	109.6	C4—C8—H8B	109.5
H10A—C10—H10B	108.1	C9—C8—H8B	109.5
C5—C6—C7	109.9 (4)	H8A—C8—H8B	108.1
C5—C6—C10	109.5 (4)	N2—C11—N1	109.0 (3)
C7—C6—C10	109.0 (4)	N2—C11—C9	123.3 (3)
C5—C6—H6A	109.5	N1—C11—C9	127.6 (3)
C7—C6—H6A	109.5	C11—N2—N3	108.6 (3)
C10—C6—H6A	109.5	C12—N3—N2	106.3 (3)
C6—C5—C4	109.8 (3)	N3—C12—N1	111.2 (3)
C6—C5—H5A	109.7	N3—C12—S1	126.8 (3)
C4—C5—H5A	109.7	N1—C12—S1	122.0 (2)
C6—C5—H5B	109.7	N4—C14—C13	113.7 (4)
C4—C5—H5B	109.7	N4—C14—H14A	108.8
H5A—C5—H5B	108.2	C13—C14—H14A	108.8
C3—C4—C5	109.5 (4)	N4—C14—H14B	108.8
C3—C4—C8	109.4 (4)	C13—C14—H14B	108.8
C5—C4—C8	109.2 (4)	H14A—C14—H14B	107.7
C3—C4—H4A	109.6	N4—C16—H16A	109.5
C5—C4—H4A	109.6	N4—C16—H16B	109.5
C8—C4—H4A	109.6	H16A—C16—H16B	109.5
C2—C3—C4	109.5 (3)	N4—C16—H16C	109.5
C2—C3—H3A	109.8	H16A—C16—H16C	109.5
C4—C3—H3A	109.8	H16B—C16—H16C	109.5
C2—C3—H3B	109.8	N1—C17—H17A	109.5
C4—C3—H3B	109.8	N1—C17—H17B	109.5
H3A—C3—H3B	108.2	H17A—C17—H17B	109.5
C14—C13—S1	109.7 (3)	N1—C17—H17C	109.5
C14—C13—H13A	109.7	H17A—C17—H17C	109.5
S1—C13—H13A	109.7	H17B—C17—H17C	109.5
C14—C13—H13B	109.7	N4—C15—H15A	109.5
S1—C13—H13B	109.7	N4—C15—H15B	109.5
H13A—C13—H13B	108.2	H15A—C15—H15B	109.5
C3—C2—C7	110.0 (4)	N4—C15—H15C	109.5
C3—C2—C1	109.7 (4)	H15A—C15—H15C	109.5
C7—C2—C1	109.6 (3)	H15B—C15—H15C	109.5
C3—C2—H2A	109.2

C11—C9—C10—C6	−177.5 (3)	C10—C9—C8—C4	58.6 (4)
C1—C9—C10—C6	57.3 (4)	C1—C9—C8—C4	−59.2 (4)
C8—C9—C10—C6	−58.8 (4)	C12—N1—C11—N2	−0.5 (4)
C9—C10—C6—C5	60.9 (4)	C17—N1—C11—N2	−179.8 (3)
C9—C10—C6—C7	−59.3 (5)	C12—N1—C11—C9	178.0 (3)
C7—C6—C5—C4	58.9 (5)	C17—N1—C11—C9	−1.3 (5)
C10—C6—C5—C4	−60.8 (5)	C10—C9—C11—N2	113.2 (4)
C6—C5—C4—C3	−59.6 (5)	C1—C9—C11—N2	−123.3 (4)
C6—C5—C4—C8	60.2 (5)	C8—C9—C11—N2	−5.3 (4)
C5—C4—C3—C2	59.8 (5)	C10—C9—C11—N1	−65.1 (4)
C8—C4—C3—C2	−59.8 (5)	C1—C9—C11—N1	58.4 (4)
C12—S1—C13—C14	−157.1 (3)	C8—C9—C11—N1	176.4 (3)
C4—C3—C2—C7	−59.9 (5)	N1—C11—N2—N3	0.8 (4)
C4—C3—C2—C1	60.7 (4)	C9—C11—N2—N3	−177.8 (3)
C3—C2—C7—C6	59.1 (5)	C11—N2—N3—C12	−0.8 (4)
C1—C2—C7—C6	−61.6 (5)	N2—N3—C12—N1	0.5 (4)
C5—C6—C7—C2	−58.6 (5)	N2—N3—C12—S1	−179.9 (3)
C10—C6—C7—C2	61.3 (5)	C11—N1—C12—N3	−0.1 (4)
C3—C2—C1—C9	−61.4 (4)	C17—N1—C12—N3	179.3 (3)
C7—C2—C1—C9	59.4 (5)	C11—N1—C12—S1	−179.7 (2)
C11—C9—C1—C2	178.2 (3)	C17—N1—C12—S1	−0.3 (5)
C10—C9—C1—C2	−57.1 (4)	C13—S1—C12—N3	3.1 (4)
C8—C9—C1—C2	59.5 (4)	C13—S1—C12—N1	−177.3 (3)
C3—C4—C8—C9	60.2 (5)	C16—N4—C14—C13	−69.9 (6)
C5—C4—C8—C9	−59.7 (5)	C15—N4—C14—C13	166.4 (5)
C11—C9—C8—C4	179.4 (3)	S1—C13—C14—N4	−58.1 (5)

Experimental details

Crystal data
Chemical formula	C₁₇H₂₈N₄S
M_r	320.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.5133 (7), 10.3779 (5), 14.3044 (8)
β (°)	106.766 (3)
V (Å³)	1778.63 (16)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.62
Crystal size (mm)	0.64 × 0.59 × 0.05

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.204, 0.923
No. of measured, independent and observed [I > 2σ(I)] reflections	3267, 3267, 2846
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.184, 1.13
No. of reflections	3267
No. of parameters	203
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.37

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

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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