4-(Pyrimidin-2-yl)-1-thia-4-aza­spiro­[4.5]decan-3-one

Neuenfeldt, P.D.; Drawanz, B.B.; Cunico, W.; Tiekink, E.R.T.; Wardell, J.L.; Wardell, S.M.S.V.

doi:10.1107/S1600536809049460

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages o3190-o3191

doi:10.1107/S1600536809049460

Open

access

4-(Pyrimidin-2-yl)-1-thia-4-azaspiro[4.5]decan-3-one

Patrícia D. Neuenfeldt,^a Bruna B. Drawanz,^a Wilson Cunico,^a,^b Edward R. T. Tiekink,^c ^* James L. Wardell ^d ‡ and Solange M. S. V. Wardell ^e

^aDepartamento de Química Orgânica, Universidade Federal de Pelotas (UFPel), Campus Universitário, s/n°, Caixa Postal 354, 96010-900 Pelotas, RS, Brazil, ^bFundação Oswaldo Cruz, Instituto de Tecnologia em Fármacos–Farmanguinhos, R. Sizenando Nabuco 100, Manguinhos, 21041-250, Rio de Janeiro, RJ, Brazil, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^dCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900 Rio de Janeiro, RJ, Brazil, and ^eCHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 November 2009; accepted 19 November 2009; online 25 November 2009)

The title compound, C₁₂H₁₅N₃OS, features an envelope conformation for the 1,3-thiazolidin-4-one ring with the S atom as the flap atom. The pyrimidine ring is almost orthogonal to the 1,3-thiazolidin-4-one ring as indicated by the N—C—C—N torsion angle of −111.96 (18)°. Supramolecular dimers are formed in the crystal structure through the agency of C—H⋯O contacts occurring between centrosymmetrically related molecules. These are linked into supramolecular tapes along [100] via C—H⋯S contacts.

Related literature

For the biological activity of thiazolidinones, see: Cunico et al. (2008a ); Solomon et al. (2007 ); Kavitha et al. (2006 ); Sharma et al. (2006 ); Ravichandran et al. (2009 ); Rao et al. (2004 ). For background to the synthesis, see: Cunico et al. (2008b ); Rawal et al. (2008 ). For related studies on the synthesis and biological evaluation of thiazolidinones, see: Cunico et al. (2006 , 2007 ).

Experimental

Crystal data

C₁₂H₁₅N₃OS
M_r = 249.33
Monoclinic, P 2₁ /n
a = 6.2466 (2) Å
b = 8.6748 (2) Å
c = 22.0439 (6) Å
β = 95.698 (1)°
V = 1188.61 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 120 K
0.26 × 0.22 × 0.14 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.658, T_max = 0.746
14004 measured reflections
2661 independent reflections
2227 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.113
S = 1.14
2661 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10a⋯S1ⁱ	0.99	2.80	3.4765 (13)	126
C10—H10b⋯O1ⁱⁱ	0.99	2.44	3.361 (2)	155
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809049460/hg2601sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809049460/hg2601Isup2.hkl

checkCIF report

Comment top

Thiazolidinones constitute an important group of heterocyclic compounds (Cunico et al., 2008a), having valuable biological uses, for example, as anti-malarial (Solomon et al., 2007), anti-microbial (Kavitha et al., 2006), anti-inflammatory (Sharma et al., 2006), and anti-viral agents, especially as anti-HIV agents (Ravichandran et al., 2009; Rao et al., 2004). The main synthetic routes to 1,3-thiazolidin-4-ones involve three components (an aldehyde, an amine and mercaptoacetic acid), either in a one- or two-step process (Cunico et al., 2008a; Rawal et al., 2006). In continuation of our research on thiazolidinones, (Cunico et al., 2006; Cunico et al., 2007: Cunico et al., 2008b), we report the structure of the title compound, 1-thia-4-azaspiro[4.5]decan-3-one, (I).

The molecule structure of (I) shows the five-membered 1,3-thiazolidin-4-one ring to adopt an envelope conformation with the S1 atom as the flap atom. The cyclohexyl ring adopts a regular chair conformation. The pyrimidine is twisted out of the plane of the 1,3-thiazolidin-4-one ring as seen in the value of the C4–N3–C11–N1 torsion angle of -111.96 (18) °. When viewed along the plane through the N1, C2, C4 and C5 atoms, the molecule, with the exception of the S1 atom, has approximate mirror symmetry.

In the crystal structure, centrosymmetric pairs associate via C—H···O contacts to form dimers, Table 1. The dimeric aggregates are linked into a supramolecular tape aligned along [1 0 0] via C—H···S contacts, Table 1 and Fig.2. The pivotal role of the C10-methylene group is noted in the stabilization of the crystal structure as each of the C10-bound H atoms forms a significant intermolecular contact.

Related literature top

For biological activity of thiazolidinones, see: Cunico et al. (2008a); Solomon et al. (2007); Kavitha et al. (2006); Sharma et al. (2006); Ravichandran et al. (2009); Rao et al. (2004). For background to the synthesis, see: Cunico et al. (2008b); Rawal et al. (2008). For related studies on the synthesis and biological evaluation of thiazolidinones, see: Cunico et al. (2006, 2007).

Experimental top

A mixture of 2-aminopyrimidine (1 mmol), cyclohexanone (2 mmol) and mercaptoacetic acid (3 mmol) in toluene (35 ml) was heated at 403 K with a Dean-Stark trap for 16 h. The reaction was cooled, washed with NaHCO₃ (3 x 20 ml), and dried with MgSO₄. The crude product was washed with a hot solvent mixture of hexane/ethyl acetate (9:1) and recrystallized from EtOH. Yield 80%. m. pt. 475–476 K. ¹H NMR (200 MHz, CDCl₃): δ 8.76 (s, 2H, aryl), 7.22 (s, 1H, aryl), 3.66 (s, 2H, H5), 2.21–1.57 (m, 10H, CH₂) p.p.m. ¹³C NMR (100 MHz, CDCl₃): δ 172.4 (CO), 158.5, 158.4, 119.3 (aryl), 75.7 (C2), 39.5 (CH₂), 38.0 (CH₂), 31.9 (C5), 24.4 (CH₂), 23.6 (CH₂) p.p.m.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. Molecular structure of (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. Supramolecular tape formation in (I) whereby dimeric aggregates sustained by C—H···O (orange dashed lines) contacts are linked via C—H···S contacts (brown dashed lines) along [1 0 0].

4-(Pyrimidin-2-yl)-1-thia-4-azaspiro[4.5]decan-3-one top

Crystal data top

C₁₂H₁₅N₃OS	F(000) = 528
M_r = 249.33	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7514 reflections
a = 6.2466 (2) Å	θ = 2.9–27.5°
b = 8.6748 (2) Å	µ = 0.26 mm⁻¹
c = 22.0439 (6) Å	T = 120 K
β = 95.698 (1)°	Block, colourless
V = 1188.61 (6) Å³	0.26 × 0.22 × 0.14 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	2661 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2227 reflections with I > 2σ(I)
10 cm confocal mirrors monochromator	R_int = 0.054
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ϕ and ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→11
T_min = 0.658, T_max = 0.746	l = −28→28
14004 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0508P)² + 0.5459P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
2661 reflections	Δρ_max = 0.36 e Å⁻³
155 parameters	Δρ_min = −0.40 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (2)

Crystal data top

C₁₂H₁₅N₃OS	V = 1188.61 (6) Å³
M_r = 249.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.2466 (2) Å	µ = 0.26 mm⁻¹
b = 8.6748 (2) Å	T = 120 K
c = 22.0439 (6) Å	0.26 × 0.22 × 0.14 mm
β = 95.698 (1)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2661 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	2227 reflections with I > 2σ(I)
T_min = 0.658, T_max = 0.746	R_int = 0.054
14004 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.14	Δρ_max = 0.36 e Å⁻³
2661 reflections	Δρ_min = −0.40 e Å⁻³
155 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.30913 (6)	0.59301 (5)	0.14394 (2)	0.02184 (17)
O1	0.19102 (19)	0.33684 (15)	0.00174 (6)	0.0215 (3)
N1	−0.2660 (2)	0.24603 (17)	0.08348 (7)	0.0189 (3)
N2	0.0587 (2)	0.09881 (17)	0.08941 (8)	0.0206 (3)
N3	0.0732 (2)	0.36704 (16)	0.09593 (6)	0.0147 (3)
C2	0.0699 (2)	0.47007 (19)	0.14937 (7)	0.0143 (3)
C4	0.1922 (2)	0.40748 (19)	0.04984 (8)	0.0161 (4)
C5	0.3225 (3)	0.5513 (2)	0.06440 (8)	0.0207 (4)
H5A	0.2630	0.6384	0.0390	0.025*
H5B	0.4737	0.5349	0.0561	0.025*
C6	0.0987 (3)	0.3792 (2)	0.20899 (8)	0.0194 (4)
H6A	0.2353	0.3207	0.2110	0.023*
H6B	−0.0204	0.3041	0.2098	0.023*
C7	0.1015 (3)	0.4855 (2)	0.26444 (8)	0.0239 (4)
H7A	0.1098	0.4224	0.3020	0.029*
H7B	0.2311	0.5517	0.2665	0.029*
C8	−0.0989 (3)	0.5870 (2)	0.26138 (8)	0.0230 (4)
H8A	−0.2266	0.5217	0.2655	0.028*
H8B	−0.0852	0.6607	0.2959	0.028*
C9	−0.1310 (3)	0.6762 (2)	0.20155 (8)	0.0186 (4)
H9A	−0.0129	0.7518	0.1999	0.022*
H9B	−0.2683	0.7338	0.1996	0.022*
C10	−0.1346 (2)	0.5672 (2)	0.14669 (8)	0.0159 (4)
H10A	−0.2612	0.4983	0.1461	0.019*
H10B	−0.1486	0.6284	0.1086	0.019*
C11	−0.0534 (2)	0.22881 (19)	0.08959 (8)	0.0144 (3)
C12	−0.3796 (3)	0.1143 (2)	0.07570 (9)	0.0214 (4)
H12	−0.5323	0.1194	0.0722	0.026*
C13	−0.2817 (3)	−0.0280 (2)	0.07264 (8)	0.0215 (4)
H13	−0.3630	−0.1200	0.0658	0.026*
C14	−0.0591 (3)	−0.0296 (2)	0.08007 (9)	0.0246 (4)
H14	0.0131	−0.1256	0.0785	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0154 (2)	0.0251 (3)	0.0259 (3)	−0.00679 (16)	0.00633 (17)	−0.00990 (19)
O1	0.0249 (6)	0.0233 (7)	0.0168 (6)	−0.0011 (5)	0.0045 (5)	−0.0020 (5)
N1	0.0163 (7)	0.0159 (8)	0.0243 (8)	−0.0001 (5)	0.0017 (6)	−0.0026 (6)
N2	0.0177 (7)	0.0163 (8)	0.0279 (9)	−0.0001 (5)	0.0023 (6)	−0.0012 (6)
N3	0.0144 (6)	0.0138 (7)	0.0161 (7)	−0.0015 (5)	0.0033 (5)	−0.0025 (6)
C2	0.0123 (7)	0.0152 (8)	0.0154 (8)	−0.0015 (6)	0.0015 (6)	−0.0035 (7)
C4	0.0137 (7)	0.0186 (9)	0.0161 (9)	0.0030 (6)	0.0016 (6)	0.0023 (7)
C5	0.0195 (8)	0.0224 (9)	0.0204 (9)	−0.0039 (7)	0.0037 (7)	0.0002 (8)
C6	0.0230 (8)	0.0171 (9)	0.0173 (9)	0.0021 (7)	−0.0019 (7)	0.0006 (7)
C7	0.0331 (10)	0.0221 (10)	0.0156 (9)	0.0008 (8)	−0.0021 (7)	0.0002 (8)
C8	0.0297 (9)	0.0236 (10)	0.0168 (9)	−0.0026 (7)	0.0071 (7)	−0.0045 (8)
C9	0.0156 (7)	0.0195 (9)	0.0208 (9)	0.0015 (6)	0.0028 (6)	−0.0026 (7)
C10	0.0133 (7)	0.0171 (9)	0.0173 (9)	0.0016 (6)	0.0017 (6)	−0.0012 (7)
C11	0.0158 (7)	0.0144 (8)	0.0130 (8)	−0.0010 (6)	0.0015 (6)	−0.0017 (6)
C12	0.0166 (8)	0.0230 (10)	0.0243 (10)	−0.0034 (7)	0.0008 (7)	−0.0023 (8)
C13	0.0243 (9)	0.0166 (9)	0.0235 (10)	−0.0050 (7)	0.0017 (7)	−0.0041 (7)
C14	0.0243 (9)	0.0164 (9)	0.0334 (11)	0.0015 (7)	0.0036 (8)	−0.0018 (8)

Geometric parameters (Å, º) top

S1—C5	1.8004 (19)	C6—H6B	0.9900
S1—C2	1.8494 (16)	C7—C8	1.527 (3)
O1—C4	1.224 (2)	C7—H7A	0.9900
N1—C11	1.330 (2)	C7—H7B	0.9900
N1—C12	1.347 (2)	C8—C9	1.525 (3)
N2—C11	1.328 (2)	C8—H8A	0.9900
N2—C14	1.339 (2)	C8—H8B	0.9900
N3—C4	1.363 (2)	C9—C10	1.533 (2)
N3—C11	1.436 (2)	C9—H9A	0.9900
N3—C2	1.480 (2)	C9—H9B	0.9900
C2—C10	1.527 (2)	C10—H10A	0.9900
C2—C6	1.528 (2)	C10—H10B	0.9900
C4—C5	1.507 (2)	C12—C13	1.382 (3)
C5—H5A	0.9900	C12—H12	0.9500
C5—H5B	0.9900	C13—C14	1.384 (2)
C6—C7	1.530 (3)	C13—H13	0.9500
C6—H6A	0.9900	C14—H14	0.9500

C5—S1—C2	93.63 (8)	H7A—C7—H7B	108.0
C11—N1—C12	115.20 (15)	C9—C8—C7	111.57 (14)
C11—N2—C14	115.15 (15)	C9—C8—H8A	109.3
C4—N3—C11	118.58 (14)	C7—C8—H8A	109.3
C4—N3—C2	119.29 (14)	C9—C8—H8B	109.3
C11—N3—C2	122.06 (13)	C7—C8—H8B	109.3
N3—C2—C10	112.34 (13)	H8A—C8—H8B	108.0
N3—C2—C6	111.29 (14)	C8—C9—C10	111.08 (15)
C10—C2—C6	110.16 (13)	C8—C9—H9A	109.4
N3—C2—S1	102.80 (10)	C10—C9—H9A	109.4
C10—C2—S1	110.96 (12)	C8—C9—H9B	109.4
C6—C2—S1	109.06 (11)	C10—C9—H9B	109.4
O1—C4—N3	124.04 (15)	H9A—C9—H9B	108.0
O1—C4—C5	123.77 (15)	C2—C10—C9	111.29 (13)
N3—C4—C5	112.18 (15)	C2—C10—H10A	109.4
C4—C5—S1	107.29 (12)	C9—C10—H10A	109.4
C4—C5—H5A	110.3	C2—C10—H10B	109.4
S1—C5—H5A	110.3	C9—C10—H10B	109.4
C4—C5—H5B	110.3	H10A—C10—H10B	108.0
S1—C5—H5B	110.3	N2—C11—N1	128.08 (15)
H5A—C5—H5B	108.5	N2—C11—N3	115.10 (13)
C2—C6—C7	111.52 (15)	N1—C11—N3	116.80 (14)
C2—C6—H6A	109.3	N1—C12—C13	122.23 (16)
C7—C6—H6A	109.3	N1—C12—H12	118.9
C2—C6—H6B	109.3	C13—C12—H12	118.9
C7—C6—H6B	109.3	C12—C13—C14	116.59 (16)
H6A—C6—H6B	108.0	C12—C13—H13	121.7
C8—C7—C6	111.59 (15)	C14—C13—H13	121.7
C8—C7—H7A	109.3	N2—C14—C13	122.69 (17)
C6—C7—H7A	109.3	N2—C14—H14	118.7
C8—C7—H7B	109.3	C13—C14—H14	118.7
C6—C7—H7B	109.3

C4—N3—C2—C10	101.41 (16)	C2—C6—C7—C8	54.95 (19)
C11—N3—C2—C10	−75.57 (19)	C6—C7—C8—C9	−53.8 (2)
C4—N3—C2—C6	−134.54 (15)	C7—C8—C9—C10	54.38 (19)
C11—N3—C2—C6	48.48 (19)	N3—C2—C10—C9	−178.32 (14)
C4—N3—C2—S1	−17.93 (17)	C6—C2—C10—C9	57.00 (18)
C11—N3—C2—S1	165.09 (12)	S1—C2—C10—C9	−63.87 (16)
C5—S1—C2—N3	19.77 (12)	C8—C9—C10—C2	−56.35 (18)
C5—S1—C2—C10	−100.52 (12)	C14—N2—C11—N1	2.2 (3)
C5—S1—C2—C6	137.96 (12)	C14—N2—C11—N3	−176.42 (16)
C11—N3—C4—O1	3.4 (2)	C12—N1—C11—N2	−0.6 (3)
C2—N3—C4—O1	−173.65 (15)	C12—N1—C11—N3	177.99 (15)
C11—N3—C4—C5	−177.71 (14)	C4—N3—C11—N2	66.8 (2)
C2—N3—C4—C5	5.2 (2)	C2—N3—C11—N2	−116.21 (17)
O1—C4—C5—S1	−170.17 (14)	C4—N3—C11—N1	−111.96 (18)
N3—C4—C5—S1	10.98 (18)	C2—N3—C11—N1	65.0 (2)
C2—S1—C5—C4	−18.17 (13)	C11—N1—C12—C13	−1.7 (3)
N3—C2—C6—C7	178.46 (13)	N1—C12—C13—C14	2.1 (3)
C10—C2—C6—C7	−56.27 (18)	C11—N2—C14—C13	−1.6 (3)
S1—C2—C6—C7	65.74 (15)	C12—C13—C14—N2	−0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10a···S1ⁱ	0.99	2.80	3.4765 (13)	126
C10—H10b···O1ⁱⁱ	0.99	2.44	3.361 (2)	155

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅N₃OS
M_r	249.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	6.2466 (2), 8.6748 (2), 22.0439 (6)
β (°)	95.698 (1)
V (Å³)	1188.61 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.26 × 0.22 × 0.14

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.658, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14004, 2661, 2227
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.113, 1.14
No. of reflections	2661
No. of parameters	155
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.40

Computer programs: , DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10a···S1ⁱ	0.99	2.80	3.4765 (13)	126
C10—H10b···O1ⁱⁱ	0.99	2.44	3.361 (2)	155

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

Footnotes

‡Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England and the valuable assistance of the staff there is gratefully acknowledged. JLW acknowledges support from FAPEMIG (Brazil).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Cunico, W., Capri, L. R., Gomes, C. R. B., Sizilio, R. H. & Wardell, S. M. S. V. (2006). Synthesis, pp. 3405–3408. Web of Science CSD CrossRef Google Scholar
Cunico, W., Gomes, C. R. B., Ferreira, M. L. G., Capri, L. R., Soares, M. & Wardell, S. M. S. V. (2007). Tetrahedron Lett. 48, 6217–6220. Web of Science CSD CrossRef CAS Google Scholar
Cunico, W., Gomes, C. R. B. & Vellasco Junior, W. T. (2008a). Mini-Rev. Org. Chem. 5, 336–344. Web of Science CrossRef CAS Google Scholar
Cunico, W., Vellasco, W. T. Jr, Moreth, M. & Gomes, C. R. B. (2008b). Lett. Org. Chem. 5, 349–352. Web of Science CrossRef CAS Google Scholar
Hooft, R. W. W. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Kavitha, C. V., Nanjunda Swamy, B. S., Mantelingu, K., Doreswamy, S., Sridhar, M. A., Prasad, J. S. & Rangappa, K. S. (2006). Bioorg. Med. Chem. 14, 2290–2290. Web of Science CSD CrossRef PubMed CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Rao, A., Chimirri, A., Ferro, S., Monforte, A. M., Monforte, P. & Maria Zappalà, M. (2004). Arkivoc, pp. 147–155. CrossRef Google Scholar
Ravichandran, V., Prashantha Kumar, B. R., Sankar, S. & Agrawal, R. K. (2009). Eur. J. Med. Chem. 44, 1180–1187. Web of Science CrossRef PubMed CAS Google Scholar
Rawal, R. K., Tripathi, R., Katti, S. B., Pannecouque, C. & De Clercq, E. (2008). Eur. J. Med. Chem. 43, 2800–2806. Web of Science CrossRef PubMed CAS Google Scholar
Sharma, S., Singh, T., Mittal, R., Saxena, K. K., Srivastava, V. K. & Kumar, A. (2006). Arch. Pharm. Chem. Life Sci. 339, 145–152. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2003). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Solomon, V. R., Haq, W., Srivastava, K., Puri, S. K. & Katti, S. B. (2007). J. Med. Chem. 50, 394–398. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar