Methyl (Z)-3-({5-[(E)-(tert-butyl-amino)-methyl-idene]-4-oxo-4,5-dihydro-1,3-thia-zol-2-yl}sulfan-yl)prop-2-enoate.

In the title compound, C(12)H(16)N(2)O(3)S(2), the S-vinyl, and tert-butyl-enamine fragments make dihedral angles of 14.19 (2) and 0.85 (2)°, respectively, with the thia-zole ring. In the crystal, mol-ecules are linked into chains with graph-set motifs C(5) along [100] by C-H⋯O inter-actions. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond.

Related literature

The thia­zole ring system can be found in natural compounds such as thia­mine (Baia, et al., 2008 ▶) and scleritodermin A (Wu & Yang, 2007 ▶). Thia­zole derivatives exhibit varied pharmaceutical properties including anti­cancer (Lesyk et al., 2006 ▶, 2007 ▶), anti­convulsant (Siddiqui & Ahsan, 2010 ▶), anti­psychotic (Satoh et al., 2009 ▶), anti­bacterial and anti­fungal (Abdel-Wahab et al., 2009 ▶; Vijaya Raj et al., 2007 ▶), anti­tubercular (Shiradkar, Murahari et al., 2007 ▶), anti­microbial (Shiradkar, Kumar et al., 2007 ▶), analgesic and anti-inflammatory (Koz’minykh et al., 2004 ▶). For synthetic methods for thiazoles, see: Andrushko et al. (2001 ▶); Bourahla et al. (2007 ▶); Fakhari et al. (2008 ▶); Potikha et al. (2008 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C12H16N2O3S2

M = 300.39

Monoclinic,

a = 6.011 (2) Å

b = 19.333 (7) Å

c = 12.870 (5) Å

β = 96.502 (8)°

V = 1485.9 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 120 K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.951, T max = 0.965

15867 measured reflections

3939 independent reflections

3125 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.108

S = 1.00

3939 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810030849/bx2284sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030849/bx2284Isup2.hkl

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

C12H16N2O3S2	F(000) = 632
Mr = 300.39	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1769 reflections
a = 6.011 (2) Å	θ = 2–25°
b = 19.333 (7) Å	µ = 0.36 mm−1
c = 12.870 (5) Å	T = 120 K
β = 96.502 (8)°	Prism, orange
V = 1485.9 (10) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3939 independent reflections
Radiation source: fine-focus sealed tube	3125 reflections with I > 2σ(I)
graphite	Rint = 0.052
phi and ω scans	θmax = 29.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −8→8
Tmin = 0.951, Tmax = 0.965	k = −26→26
15867 measured reflections	l = −17→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.010P)2 + 1.980P] where P = (Fo2 + 2Fc2)/3
3939 reflections	(Δ/σ)max = 0.001
177 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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 > 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.

	x	y	z	Uiso*/Ueq
S1	0.50629 (8)	0.53451 (3)	0.63467 (4)	0.03196 (13)
S2	0.20485 (8)	0.62005 (3)	0.49185 (4)	0.03050 (13)
O1	0.0477 (2)	0.46226 (9)	0.78666 (12)	0.0376 (4)
O2	0.1152 (3)	0.72490 (9)	0.34743 (13)	0.0459 (4)
O3	−0.2299 (3)	0.75225 (9)	0.27204 (13)	0.0438 (4)
N1	0.0743 (3)	0.53679 (9)	0.64593 (13)	0.0282 (3)
N2	0.4543 (3)	0.40971 (9)	0.87697 (14)	0.0318 (4)
H2N	0.3101	0.4070	0.8892	0.038*
C1	0.2330 (3)	0.56032 (10)	0.59558 (15)	0.0258 (4)
C2	0.4049 (3)	0.48646 (10)	0.73331 (15)	0.0269 (4)
C3	0.1648 (3)	0.49260 (10)	0.72696 (15)	0.0272 (4)
C4	−0.0858 (3)	0.62176 (10)	0.46463 (15)	0.0276 (4)
H4A	−0.1700	0.5904	0.5014	0.033*
C5	−0.1981 (4)	0.66419 (10)	0.39564 (16)	0.0305 (4)
H5A	−0.3567	0.6608	0.3840	0.037*
C6	−0.0849 (4)	0.71564 (11)	0.33756 (16)	0.0324 (4)
C7	−0.1334 (6)	0.80731 (14)	0.2156 (2)	0.0577 (7)
H7A	−0.2472	0.8259	0.1624	0.087*
H7B	−0.0076	0.7891	0.1817	0.087*
H7C	−0.0800	0.8442	0.2645	0.087*
C8	0.5374 (3)	0.44672 (10)	0.80461 (16)	0.0294 (4)
H8A	0.6945	0.4460	0.8014	0.035*
C9	0.5922 (4)	0.36708 (12)	0.95625 (17)	0.0361 (5)
C10	0.4347 (5)	0.3335 (2)	1.0225 (3)	0.0814 (12)
H10A	0.3303	0.3038	0.9788	0.122*
H10B	0.3505	0.3692	1.0555	0.122*
H10C	0.5197	0.3055	1.0767	0.122*
C11	0.7586 (5)	0.41439 (16)	1.0220 (2)	0.0563 (7)
H11A	0.6761	0.4501	1.0558	0.084*
H11B	0.8583	0.4364	0.9766	0.084*
H11C	0.8475	0.3869	1.0756	0.084*
C12	0.7262 (5)	0.31403 (14)	0.9007 (2)	0.0548 (7)
H12A	0.6231	0.2844	0.8562	0.082*
H12B	0.8157	0.2856	0.9529	0.082*
H12C	0.8258	0.3382	0.8575	0.082*

	U11	U22	U33	U12	U13	U23
S1	0.0213 (2)	0.0381 (3)	0.0374 (3)	0.00031 (19)	0.00743 (19)	0.0062 (2)
S2	0.0267 (2)	0.0302 (2)	0.0356 (3)	−0.00246 (19)	0.00762 (19)	0.0066 (2)
O1	0.0256 (7)	0.0497 (9)	0.0387 (8)	−0.0037 (6)	0.0087 (6)	0.0120 (7)
O2	0.0472 (10)	0.0462 (10)	0.0439 (9)	−0.0114 (8)	0.0037 (7)	0.0139 (8)
O3	0.0543 (10)	0.0398 (9)	0.0380 (9)	0.0094 (8)	0.0081 (7)	0.0129 (7)
N1	0.0239 (8)	0.0303 (8)	0.0313 (8)	−0.0003 (6)	0.0068 (6)	0.0025 (7)
N2	0.0248 (8)	0.0362 (9)	0.0348 (9)	0.0008 (7)	0.0058 (7)	0.0050 (7)
C1	0.0234 (9)	0.0245 (9)	0.0296 (9)	−0.0002 (7)	0.0044 (7)	−0.0018 (7)
C2	0.0253 (9)	0.0271 (9)	0.0289 (10)	−0.0021 (7)	0.0061 (7)	0.0007 (7)
C3	0.0249 (9)	0.0284 (9)	0.0285 (9)	−0.0022 (7)	0.0043 (7)	−0.0007 (8)
C4	0.0274 (9)	0.0264 (9)	0.0300 (10)	−0.0016 (7)	0.0081 (7)	−0.0017 (7)
C5	0.0324 (10)	0.0292 (10)	0.0302 (10)	0.0011 (8)	0.0049 (8)	−0.0019 (8)
C6	0.0431 (12)	0.0279 (10)	0.0264 (10)	0.0009 (9)	0.0043 (8)	−0.0012 (8)
C7	0.080 (2)	0.0452 (14)	0.0496 (15)	0.0083 (14)	0.0150 (14)	0.0224 (12)
C8	0.0236 (9)	0.0312 (10)	0.0339 (10)	−0.0012 (7)	0.0049 (7)	−0.0029 (8)
C9	0.0378 (11)	0.0367 (11)	0.0332 (11)	0.0052 (9)	0.0018 (9)	0.0067 (9)
C10	0.0503 (17)	0.109 (3)	0.087 (2)	0.0109 (18)	0.0177 (16)	0.059 (2)
C11	0.0666 (18)	0.0566 (17)	0.0426 (14)	0.0052 (14)	−0.0073 (13)	−0.0017 (12)
C12	0.0664 (18)	0.0447 (14)	0.0521 (16)	0.0155 (13)	0.0012 (13)	0.0014 (12)

S1—C1	1.736 (2)	C5—H5A	0.9500
S1—C2	1.738 (2)	C7—H7A	0.9800
S2—C4	1.743 (2)	C7—H7B	0.9800
S2—C1	1.759 (2)	C7—H7C	0.9800
O1—C3	1.246 (2)	C8—H8A	0.9500
O2—C6	1.209 (3)	C9—C10	1.493 (4)
O3—C6	1.343 (3)	C9—C12	1.530 (3)
O3—C7	1.447 (3)	C9—C11	1.537 (4)
N1—C1	1.295 (2)	C10—H10A	0.9800
N1—C3	1.409 (3)	C10—H10B	0.9800
N2—C8	1.317 (3)	C10—H10C	0.9800
N2—C9	1.488 (3)	C11—H11A	0.9800
N2—H2N	0.9000	C11—H11B	0.9800
C2—C8	1.379 (3)	C11—H11C	0.9800
C2—C3	1.441 (3)	C12—H12A	0.9800
C4—C5	1.335 (3)	C12—H12B	0.9800
C4—H4A	0.9500	C12—H12C	0.9800
C5—C6	1.458 (3)
C1—S1—C2	88.09 (10)	H7A—C7—H7C	109.5
C4—S2—C1	99.97 (9)	H7B—C7—H7C	109.5
C6—O3—C7	115.7 (2)	N2—C8—C2	122.48 (19)
C1—N1—C3	109.79 (16)	N2—C8—H8A	118.8
C8—N2—C9	124.02 (18)	C2—C8—H8A	118.8
C8—N2—H2N	127.3	N2—C9—C10	107.0 (2)
C9—N2—H2N	108.6	N2—C9—C12	109.43 (19)
N1—C1—S1	118.72 (15)	C10—C9—C12	112.1 (3)
N1—C1—S2	126.69 (15)	N2—C9—C11	108.98 (19)
S1—C1—S2	114.53 (11)	C10—C9—C11	111.1 (2)
C8—C2—C3	125.64 (18)	C12—C9—C11	108.2 (2)
C8—C2—S1	124.06 (15)	C9—C10—H10A	109.5
C3—C2—S1	110.26 (14)	C9—C10—H10B	109.5
O1—C3—N1	122.95 (18)	H10A—C10—H10B	109.5
O1—C3—C2	123.95 (18)	C9—C10—H10C	109.5
N1—C3—C2	113.10 (16)	H10A—C10—H10C	109.5
C5—C4—S2	124.43 (16)	H10B—C10—H10C	109.5
C5—C4—H4A	117.8	C9—C11—H11A	109.5
S2—C4—H4A	117.8	C9—C11—H11B	109.5
C4—C5—C6	122.0 (2)	H11A—C11—H11B	109.5
C4—C5—H5A	119.0	C9—C11—H11C	109.5
C6—C5—H5A	119.0	H11A—C11—H11C	109.5
O2—C6—O3	123.7 (2)	H11B—C11—H11C	109.5
O2—C6—C5	124.3 (2)	C9—C12—H12A	109.5
O3—C6—C5	111.96 (19)	C9—C12—H12B	109.5
O3—C7—H7A	109.5	H12A—C12—H12B	109.5
O3—C7—H7B	109.5	C9—C12—H12C	109.5
H7A—C7—H7B	109.5	H12A—C12—H12C	109.5
O3—C7—H7C	109.5	H12B—C12—H12C	109.5
C3—N1—C1—S1	0.2 (2)	S1—C2—C3—N1	−1.8 (2)
C3—N1—C1—S2	−177.08 (15)	C1—S2—C4—C5	174.49 (18)
C2—S1—C1—N1	−1.00 (17)	S2—C4—C5—C6	−1.9 (3)
C2—S1—C1—S2	176.56 (12)	C7—O3—C6—O2	−2.9 (3)
C4—S2—C1—N1	−11.2 (2)	C7—O3—C6—C5	176.5 (2)
C4—S2—C1—S1	171.44 (11)	C4—C5—C6—O2	−1.0 (3)
C1—S1—C2—C8	179.57 (19)	C4—C5—C6—O3	179.54 (19)
C1—S1—C2—C3	1.47 (15)	C9—N2—C8—C2	−179.01 (19)
C1—N1—C3—O1	−179.05 (19)	C3—C2—C8—N2	−0.7 (3)
C1—N1—C3—C2	1.0 (2)	S1—C2—C8—N2	−178.46 (16)
C8—C2—C3—O1	0.3 (3)	C8—N2—C9—C10	−179.7 (3)
S1—C2—C3—O1	178.34 (17)	C8—N2—C9—C12	−58.0 (3)
C8—C2—C3—N1	−179.81 (19)	C8—N2—C9—C11	60.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.90	2.21	2.777 (2)	120
C4—H4A···N1	0.95	2.46	2.926 (3)	110
C8—H8A···O1i	0.95	2.18	3.117 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1	0.90	2.21	2.777 (2)	120
C8—H8A⋯O1i	0.95	2.18	3.117 (3)	171

Symmetry code: (i) .