1-(Adamantan-1-yl)-3-(4-fluoro­phen­yl)thio­urea

Demirtaş, G.; Dege, N.; Al-Shehri, M.M.; El-Emam, A.A.; El-Brollosy, N.R.; Büyükgüngör, O.

doi:10.1107/S1600536812017515

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1523

doi:10.1107/S1600536812017515

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1-(Adamantan-1-yl)-3-(4-fluorophenyl)thiourea

Güneş Demirtaş,^a ^* Necmi Dege,^a Mona M. Al-Shehri,^b Ali A. El-Emam,^b Nasser R. El-Brollosy ^b and Orhan Büyükgüngör ^a

^aOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, and ^bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, 11451 Riyadh, Saudi Arabia
^*Correspondence e-mail: gunesd@omu.edu.tr

(Received 11 April 2012; accepted 19 April 2012; online 25 April 2012)

In the title molecule, C₁₇H₂₁FN₂S, the mean planes of the benzene ring and the thiourea fragment form a dihedral angle of 61.93 (9)°. In the crystal, pairs of weak N—H⋯S interactions link the molecules, forming inversion dimers.

Related literature

For background to the biological activity of adamantane and thiourea derivatives, see: Vernier et al. (1969 ); El-Emam et al. (2004 ); Li et al. (2009 ); Hunter et al. (2008 ); Kadi et al. (2007 , 2010 ). For the crystal structures of related adamantane derivatives, see: Kadi et al. (2011 ); Almutairi et al. (2012 ); Al-Abdullah et al. (2012 ).

Experimental

Crystal data

C₁₇H₂₁FN₂S
M_r = 304.42
Triclinic, $[P \overline 1]$
a = 6.4274 (5) Å
b = 11.4727 (9) Å
c = 11.5870 (9) Å
α = 113.510 (6)°
β = 94.721 (6)°
γ = 94.837 (6)°
V = 774.39 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.80 × 0.35 × 0.11 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.847, T_max = 0.977
11154 measured reflections
3048 independent reflections
2224 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.118
S = 1.01
3048 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S1ⁱ	0.86	2.67	3.3939 (19)	142
Symmetry code: (i) -x, -y+2, -z+1.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812017515/cv5285sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812017515/cv5285Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812017515/cv5285Isup3.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 and anti-inflammatory activities (Kadi et al., 2007, 2010). In addition, 1,3-disubstituted thiourea derivatives were reported to possess potent antiviral activity (Li et al., 2009; Hunter et al., 2008). In continuation of our structural studies of adamantane derivatives (Kadi et al., 2011; Al-Abdullah et al., 2012; Almutairi et al., 2012), we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the adamantyl and fluorobenzene fragments are bridged by thiourea fragment. The C—C single bond distances range from 1.514 (4) Å to 1.537 (3) Å and C≐C bond distances for benzene ring range from 1.359 (4) Å to 1.383 (3) Å. The torsion angle of C6—C1—N1—C7 is 62.7 (3)° and the bond distance between the F and C atoms is 1.362 (3) Å. The weak intermolecular N1—H1···S1 hydrogen bond (Table 1) link two molecules into centrosymmetric dimer.

Related literature top

For background to the biological activity of adamantane and thiourea derivatives, see: Vernier et al. (1969); El-Emam et al. (2004); Li et al. (2009); Hunter et al. (2008); Kadi et al. (2007, 2010). For the crystal structures of related adamantane derivatives, see: Kadi et al. (2011); Almutairi et al. (2012); Al-Abdullah et al. (2012).

Experimental top

A mixture of 1-adamantylamine (1.51 g m, 0.01 mol) and 4-fluorophenyl isothiocyanate (1.53 g m, 0.01 mol), in ethanol (10 ml), was heated under reflux for 4 h. On cooling, the precipitated crude product was filtered, dried and crystallized from ethanol to yield 2.68 g m (88%) of the title compound (C₁₇H₂₁FN₂S) as colourless crystals. M.P.: 169–171 ^oC. Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution of the title compound in EtOH/CHCl₃ (1:1) at room temperature. ¹H NMR (DMSO-d₆, 500.13 MHz): d 1.64 (s, 6H, Adamantane-H), 2.06 (s, 3H, Adamantane-H), 2.23 (s, 6H, Adamantane-H), 7.10–7.14 (m, 2H, Ar—H), 7.24 (s, 1H, NH), 7.43 (d, 2H, Ar—H, J = 6.5 Hz), 9.25 (s, 1H, NH). ¹³C NMR (DMSO-d₆, 125.76 MHz): 28.98, 35.94, 40.80, 53.24 (Adamantane-C), 114.72, 125.49, 135.79, 157.66 (Ar—C), 179.06 (C=S).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

1-(Adamantan-1-yl)-3-(4-fluorophenyl)thiourea top

Crystal data top

C₁₇H₂₁FN₂S	Z = 2
M_r = 304.42	F(000) = 324
Triclinic, P1	D_x = 1.306 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.4274 (5) Å	Cell parameters from 14319 reflections
b = 11.4727 (9) Å	θ = 3.2–27.9°
c = 11.5870 (9) Å	µ = 0.22 mm⁻¹
α = 113.510 (6)°	T = 296 K
β = 94.721 (6)°	Prism, colourless
γ = 94.837 (6)°	0.80 × 0.35 × 0.11 mm
V = 774.39 (10) Å³

Data collection top

Stoe IPDS 2 diffractometer	3048 independent reflections
Radiation source: fine-focus sealed tube	2224 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
rotation method scans	θ_max = 26.0°, θ_min = 3.2°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −7→7
T_min = 0.847, T_max = 0.977	k = −14→14
11154 measured reflections	l = −14→14

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0575P)² + 0.0575P] where P = (F_o² + 2F_c²)/3
3048 reflections	(Δ/σ)_max = 0.001
190 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₂₁FN₂S	γ = 94.837 (6)°
M_r = 304.42	V = 774.39 (10) Å³
Triclinic, P1	Z = 2
a = 6.4274 (5) Å	Mo Kα radiation
b = 11.4727 (9) Å	µ = 0.22 mm⁻¹
c = 11.5870 (9) Å	T = 296 K
α = 113.510 (6)°	0.80 × 0.35 × 0.11 mm
β = 94.721 (6)°

Data collection top

Stoe IPDS 2 diffractometer	3048 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2224 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.977	R_int = 0.078
11154 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
3048 reflections	Δρ_min = −0.21 e Å⁻³
190 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
C1	0.3269 (3)	0.96011 (19)	0.2888 (2)	0.0449 (5)
C2	0.4940 (4)	1.0491 (2)	0.3639 (2)	0.0522 (6)
H2	0.4918	1.0899	0.4510	0.063*
C3	0.6639 (4)	1.0781 (2)	0.3108 (3)	0.0603 (6)
H3	0.7754	1.1393	0.3608	0.072*
C4	0.6651 (4)	1.0152 (2)	0.1836 (3)	0.0579 (6)
C5	0.5006 (4)	0.9293 (2)	0.1057 (2)	0.0587 (6)
H5	0.5045	0.8894	0.0186	0.070*
C6	0.3282 (4)	0.9030 (2)	0.1589 (2)	0.0538 (6)
H6	0.2125	0.8467	0.1073	0.065*
C7	0.0960 (3)	0.80999 (19)	0.3412 (2)	0.0434 (5)
C8	0.2048 (3)	0.58337 (18)	0.25944 (19)	0.0371 (4)
C9	−0.0095 (3)	0.50477 (19)	0.1946 (2)	0.0414 (5)
H9A	−0.0449	0.5111	0.1145	0.050*
H9B	−0.1178	0.5382	0.2481	0.050*
C10	0.0005 (3)	0.3639 (2)	0.1715 (2)	0.0484 (6)
H10	−0.1371	0.3139	0.1315	0.058*
C11	0.0577 (4)	0.3544 (2)	0.2966 (3)	0.0555 (6)
H11A	0.0617	0.2654	0.2821	0.067*
H11B	−0.0482	0.3873	0.3521	0.067*
C12	0.2722 (4)	0.4314 (2)	0.3594 (3)	0.0553 (6)
H12	0.3091	0.4242	0.4398	0.066*
C13	0.2620 (3)	0.5721 (2)	0.3845 (2)	0.0479 (5)
H13A	0.1572	0.6054	0.4407	0.057*
H13B	0.3972	0.6221	0.4255	0.057*
C14	0.3707 (3)	0.5295 (2)	0.1712 (2)	0.0467 (5)
H14A	0.3351	0.5364	0.0914	0.056*
H14B	0.5073	0.5789	0.2097	0.056*
C15	0.3806 (3)	0.3894 (2)	0.1469 (2)	0.0524 (6)
H15	0.4880	0.3562	0.0912	0.063*
C16	0.1668 (3)	0.3114 (2)	0.0831 (3)	0.0565 (6)
H16A	0.1725	0.2219	0.0662	0.068*
H16B	0.1305	0.3176	0.0030	0.068*
C17	0.4373 (3)	0.3789 (2)	0.2715 (3)	0.0630 (7)
H17A	0.5744	0.4269	0.3112	0.076*
H17B	0.4443	0.2899	0.2563	0.076*
N1	0.1550 (3)	0.92729 (17)	0.34457 (19)	0.0536 (5)
H1	0.0822	0.9873	0.3838	0.064*
N2	0.2119 (3)	0.71831 (16)	0.27757 (18)	0.0471 (5)
H2A	0.3069	0.7428	0.2410	0.057*
F1	0.8343 (3)	1.04002 (17)	0.12965 (18)	0.0899 (6)
S1	−0.10933 (9)	0.78832 (5)	0.41551 (6)	0.0557 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0514 (11)	0.0311 (10)	0.0520 (14)	0.0071 (8)	0.0101 (10)	0.0159 (9)
C2	0.0629 (13)	0.0420 (12)	0.0466 (13)	0.0011 (10)	0.0050 (11)	0.0140 (10)
C3	0.0571 (13)	0.0512 (14)	0.0647 (17)	−0.0051 (11)	0.0007 (12)	0.0191 (12)
C4	0.0603 (14)	0.0453 (12)	0.0703 (17)	0.0038 (10)	0.0204 (12)	0.0244 (12)
C5	0.0801 (16)	0.0432 (12)	0.0509 (15)	0.0033 (11)	0.0193 (13)	0.0159 (11)
C6	0.0588 (13)	0.0428 (12)	0.0504 (14)	−0.0041 (10)	0.0040 (11)	0.0119 (11)
C7	0.0427 (10)	0.0373 (11)	0.0453 (13)	0.0058 (8)	0.0080 (9)	0.0110 (9)
C8	0.0326 (9)	0.0344 (10)	0.0412 (12)	0.0041 (7)	0.0065 (8)	0.0121 (8)
C9	0.0341 (9)	0.0443 (11)	0.0417 (12)	0.0075 (8)	0.0021 (8)	0.0134 (9)
C10	0.0326 (10)	0.0395 (11)	0.0594 (15)	−0.0005 (8)	0.0024 (9)	0.0076 (10)
C11	0.0512 (12)	0.0471 (12)	0.0744 (17)	0.0048 (10)	0.0152 (12)	0.0302 (12)
C12	0.0545 (13)	0.0573 (14)	0.0604 (15)	0.0069 (10)	−0.0038 (11)	0.0328 (12)
C13	0.0424 (11)	0.0506 (13)	0.0446 (13)	0.0009 (9)	−0.0025 (10)	0.0157 (10)
C14	0.0389 (10)	0.0433 (11)	0.0569 (14)	0.0084 (8)	0.0149 (10)	0.0171 (10)
C15	0.0395 (11)	0.0414 (11)	0.0711 (17)	0.0119 (9)	0.0176 (11)	0.0144 (11)
C16	0.0519 (12)	0.0405 (12)	0.0624 (16)	0.0068 (10)	0.0092 (11)	0.0051 (11)
C17	0.0415 (12)	0.0531 (14)	0.098 (2)	0.0128 (10)	0.0018 (13)	0.0353 (14)
N1	0.0594 (11)	0.0350 (9)	0.0655 (13)	0.0110 (8)	0.0234 (10)	0.0158 (9)
N2	0.0465 (9)	0.0376 (9)	0.0614 (12)	0.0091 (7)	0.0235 (9)	0.0207 (9)
F1	0.0811 (10)	0.0808 (11)	0.1042 (14)	−0.0079 (8)	0.0415 (10)	0.0320 (10)
S1	0.0505 (3)	0.0416 (3)	0.0672 (4)	0.0066 (2)	0.0261 (3)	0.0106 (3)

Geometric parameters (Å, º) top

C1—C2	1.381 (3)	C10—C16	1.533 (3)
C1—C6	1.383 (3)	C10—H10	0.9800
C1—N1	1.421 (3)	C11—C12	1.526 (3)
C2—C3	1.376 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—H11B	0.9700
C3—C4	1.359 (4)	C12—C17	1.524 (3)
C3—H3	0.9300	C12—C13	1.530 (3)
C4—F1	1.362 (3)	C12—H12	0.9800
C4—C5	1.364 (4)	C13—H13A	0.9700
C5—C6	1.380 (3)	C13—H13B	0.9700
C5—H5	0.9300	C14—C15	1.526 (3)
C6—H6	0.9300	C14—H14A	0.9700
C7—N2	1.345 (2)	C14—H14B	0.9700
C7—N1	1.351 (3)	C15—C17	1.514 (4)
C7—S1	1.687 (2)	C15—C16	1.527 (3)
C8—N2	1.473 (2)	C15—H15	0.9800
C8—C13	1.524 (3)	C16—H16A	0.9700
C8—C14	1.533 (3)	C16—H16B	0.9700
C8—C9	1.535 (3)	C17—H17A	0.9700
C9—C10	1.537 (3)	C17—H17B	0.9700
C9—H9A	0.9700	N1—H1	0.8600
C9—H9B	0.9700	N2—H2A	0.8600
C10—C11	1.514 (4)

C2—C1—C6	119.4 (2)	H11A—C11—H11B	108.2
C2—C1—N1	120.3 (2)	C17—C12—C11	109.3 (2)
C6—C1—N1	120.3 (2)	C17—C12—C13	109.9 (2)
C3—C2—C1	120.5 (2)	C11—C12—C13	109.09 (18)
C3—C2—H2	119.7	C17—C12—H12	109.5
C1—C2—H2	119.7	C11—C12—H12	109.5
C4—C3—C2	118.5 (2)	C13—C12—H12	109.5
C4—C3—H3	120.7	C8—C13—C12	109.58 (18)
C2—C3—H3	120.7	C8—C13—H13A	109.8
C3—C4—F1	119.4 (2)	C12—C13—H13A	109.8
C3—C4—C5	122.7 (2)	C8—C13—H13B	109.8
F1—C4—C5	117.8 (2)	C12—C13—H13B	109.8
C4—C5—C6	118.5 (2)	H13A—C13—H13B	108.2
C4—C5—H5	120.7	C15—C14—C8	110.05 (17)
C6—C5—H5	120.7	C15—C14—H14A	109.7
C5—C6—C1	120.2 (2)	C8—C14—H14A	109.7
C5—C6—H6	119.9	C15—C14—H14B	109.7
C1—C6—H6	119.9	C8—C14—H14B	109.7
N2—C7—N1	115.40 (17)	H14A—C14—H14B	108.2
N2—C7—S1	125.04 (16)	C17—C15—C14	109.59 (19)
N1—C7—S1	119.56 (14)	C17—C15—C16	109.8 (2)
N2—C8—C13	111.51 (17)	C14—C15—C16	109.42 (18)
N2—C8—C14	105.19 (16)	C17—C15—H15	109.3
C13—C8—C14	109.26 (17)	C14—C15—H15	109.3
N2—C8—C9	112.54 (16)	C16—C15—H15	109.3
C13—C8—C9	109.88 (16)	C15—C16—C10	108.83 (18)
C14—C8—C9	108.27 (16)	C15—C16—H16A	109.9
C8—C9—C10	109.31 (16)	C10—C16—H16A	109.9
C8—C9—H9A	109.8	C15—C16—H16B	109.9
C10—C9—H9A	109.8	C10—C16—H16B	109.9
C8—C9—H9B	109.8	H16A—C16—H16B	108.3
C10—C9—H9B	109.8	C15—C17—C12	109.70 (18)
H9A—C9—H9B	108.3	C15—C17—H17A	109.7
C11—C10—C16	109.86 (19)	C12—C17—H17A	109.7
C11—C10—C9	109.71 (18)	C15—C17—H17B	109.7
C16—C10—C9	109.11 (19)	C12—C17—H17B	109.7
C11—C10—H10	109.4	H17A—C17—H17B	108.2
C16—C10—H10	109.4	C7—N1—C1	125.69 (17)
C9—C10—H10	109.4	C7—N1—H1	117.2
C10—C11—C12	109.87 (19)	C1—N1—H1	117.2
C10—C11—H11A	109.7	C7—N2—C8	131.37 (17)
C12—C11—H11A	109.7	C7—N2—H2A	114.3
C10—C11—H11B	109.7	C8—N2—H2A	114.3
C12—C11—H11B	109.7

C6—C1—C2—C3	−2.1 (3)	C11—C12—C13—C8	−60.2 (2)
N1—C1—C2—C3	177.9 (2)	N2—C8—C14—C15	179.09 (18)
C1—C2—C3—C4	−1.4 (4)	C13—C8—C14—C15	59.3 (2)
C2—C3—C4—F1	−178.3 (2)	C9—C8—C14—C15	−60.4 (2)
C2—C3—C4—C5	3.3 (4)	C8—C14—C15—C17	−59.6 (2)
C3—C4—C5—C6	−1.6 (4)	C8—C14—C15—C16	60.8 (3)
F1—C4—C5—C6	179.9 (2)	C17—C15—C16—C10	59.9 (2)
C4—C5—C6—C1	−1.9 (4)	C14—C15—C16—C10	−60.4 (3)
C2—C1—C6—C5	3.7 (3)	C11—C10—C16—C15	−59.5 (3)
N1—C1—C6—C5	−176.2 (2)	C9—C10—C16—C15	60.9 (3)
N2—C8—C9—C10	176.37 (17)	C14—C15—C17—C12	59.6 (2)
C13—C8—C9—C10	−58.7 (2)	C16—C15—C17—C12	−60.6 (2)
C14—C8—C9—C10	60.5 (2)	C11—C12—C17—C15	59.8 (3)
C8—C9—C10—C11	59.0 (2)	C13—C12—C17—C15	−59.8 (3)
C8—C9—C10—C16	−61.4 (2)	N2—C7—N1—C1	−0.8 (3)
C16—C10—C11—C12	59.6 (2)	S1—C7—N1—C1	178.58 (18)
C9—C10—C11—C12	−60.3 (2)	C2—C1—N1—C7	−117.2 (3)
C10—C11—C12—C17	−59.4 (2)	C6—C1—N1—C7	62.7 (3)
C10—C11—C12—C13	60.7 (2)	N1—C7—N2—C8	176.0 (2)
N2—C8—C13—C12	−174.86 (16)	S1—C7—N2—C8	−3.4 (4)
C14—C8—C13—C12	−59.0 (2)	C13—C8—N2—C7	−64.7 (3)
C9—C8—C13—C12	59.6 (2)	C14—C8—N2—C7	177.0 (2)
C17—C12—C13—C8	59.6 (2)	C9—C8—N2—C7	59.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.67	3.3939 (19)	142

Symmetry code: (i) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₂₁FN₂S
M_r	304.42
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.4274 (5), 11.4727 (9), 11.5870 (9)
α, β, γ (°)	113.510 (6), 94.721 (6), 94.837 (6)
V (Å³)	774.39 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.80 × 0.35 × 0.11

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.847, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	11154, 3048, 2224
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.118, 1.01
No. of reflections	3048
No. of parameters	190
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S1ⁱ	0.86	2.67	3.3939 (19)	142.3

Symmetry code: (i) −x, −y+2, −z+1.

Acknowledgements

The authors thank Ondokuz Mayıs University Research Fund for financial support. The financial support of the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, is greatly appreciated.

References

Al-Abdullah, E. S., Asiri, H. H., El-Emam, A. & Ng, S. W. (2012). Acta Cryst. E68, o345. Web of Science CSD CrossRef IUCr Journals Google Scholar
Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656. CSD CrossRef IUCr Journals Google Scholar
El-Emam, A. A., Al-Deeb, O. A., Al-Omar, M. A. & Lehmann, J. (2004). Bioorg. Med. Chem. 12, 5107–5113. Web of Science CrossRef PubMed CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hunter, R., Younis, Y., Muhanji, C. I., Curtin, T. L., Naidoo, K. J., Petersen, M., Bailey, C. M., Basavapathruni, A. & Anderson, K. S. (2008). Bioorg. Med. Chem. 16, 10270–10280. Web of Science CrossRef PubMed CAS Google Scholar
Kadi, A. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Eur. J. Med. Chem. 45, 5006–5011. Web of Science CrossRef CAS PubMed Google Scholar
Kadi, A. A., Alanzi, A. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o3127. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kadi, A. A., El-Brollosy, N. R., Al-Deeb, O. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2007). Eur. J. Med. Chem. 42, 235–242. Web of Science CrossRef PubMed CAS Google Scholar
Li, J., Tan, Z., Tang, S., Hewlett, I., Pang, R., He, M., He, S., Tian, B., Chen, K. & Yang, M. (2009). Bioorg. Med. Chem. 17, 3177–3188. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Vernier, V. G., Harmon, J. B., Stump, J. M., Lynes, T. L., Marvel, M. P. & Smith, D. H. (1969). Toxicol. Appl. Pharmacol. 15, 642–665. CrossRef CAS PubMed Web of Science Google Scholar