4-(Pyrimidin-2-yl)-1-thia-4-aza-spiro-[4.5]decan-3-one.

The title compound, C(12)H(15)N(3)OS, features an envelope conformation for the 1,3-thia-zolidin-4-one ring with the S atom as the flap atom. The pyrimidine ring is almost orthogonal to the 1,3-thia-zolidin-4-one ring as indicated by the N-C-C-N torsion angle of -111.96 (18)°. Supra-molecular dimers are formed in the crystal structure through the agency of C-H⋯O contacts occurring between centrosymmetrically related mol-ecules. These are linked into supra-molecular 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 = 249.33

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.113

S = 1.14

2661 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.40 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C12H15N3OS	F(000) = 528
Mr = 249.33	Dx = 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

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	Rint = 0.054
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −8→7
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→11
Tmin = 0.658, Tmax = 0.746	l = −28→28
14004 measured reflections

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(Fo2) + (0.0508P)2 + 0.5459P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
2661 reflections	Δρmax = 0.36 e Å−3
155 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .