Methyl (Z)-3-({5-[(E)-(tert-butyl­amino)­methyl­idene]-4-oxo-4,5-dihydro-1,3-thia­zol-2-yl}sulfan­yl)prop-2-enoate

Baharfar, R.; Porahmad, N.; Vahdat, S.M.

doi:10.1107/S1600536810030849

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages o2344-o2345

https://doi.org/10.1107/S1600536810030849

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Methyl (Z)-3-({5-[(E)-(tert-butylamino)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}sulfanyl)prop-2-enoate

Robabeh Baharfar,^a ^* Nasim Porahmad ^a and S. Mohammad Vahdat ^a

^aDepartment of Chemistry, University of Mazandaran, 47415 Babolsar, Iran
^*Correspondence e-mail: baharfar@umz.ac.ir

(Received 6 June 2010; accepted 2 August 2010; online 18 August 2010)

In the title compound, C₁₂H₁₆N₂O₃S₂, the S-vinyl, and tert-butylenamine fragments make dihedral angles of 14.19 (2) and 0.85 (2)°, respectively, with the thiazole ring. In the crystal, molecules are linked into chains with graph-set motifs C(5) along [100] by C—H⋯O interactions. The molecular conformation is stabilized by an intramolecular 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_r = 300.39
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.046
wR(F²) = 0.108
S = 1.00
3939 reflections
177 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) x+1, y, z.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030849/bx2284Isup2.hkl

checkCIF report

Comment top

The thiazole ring system can be fined in natural compounds like thiamine (vitamin B₁) (Baia, et al., 2008), bistratamide H, archazolid A & B, siomycin A, didmolamide A, scleritodermin A, etc. (Wu & Yang, 2007). Thiazole derivatives exhibit different pharmaceutical properties, among them are: anticancer (Lesyk et al., 2007; & Lesyk et al., 2006), anticonvulsant (Siddiqui & Ahsan, 2010), antipsychotic-like (Satoh et al., 2009), antibacterial, 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) activities. These compounds have been synthesized using different methods (Andrushko et al., 2001; & Bourahla et al., 2007; & Fakhari et al., 2008; & Potikha et al., 2008). We have succeeded in synthesizing a thiazole derivative using a three step reaction. methods for theirWe report here the synthesis and crystal structure of the title compound (I). The molecular structure of (I) is illustrated in Fig 1. The fragments S-vinyl, and tert-butyl enamine makes angles of 14.19 (2) and 0.85 (2)° with the thiazole ring. In the crystal the molecules are linked into chains along [100] direction with graph-set notation C(5) motifs by a C—H···O interaction, (Bernstein, et al., 1995) Fig. 2. The molecular conformation is stabilized by two intramolecular N—H···O and C—H···O hydrogen bonds. Z-configuration was assigned to the geometry of S-vinyl system on the basis of torsion angle of -1.86 (4)° between atom S₂ and methoxy carbonyl group.

Related literature top

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 methods for their synthesis, 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 top

To a magnetically stirred solution of rhodanine (0.27 g, 2 mmol) and methyl acetylenecarboxylate (0.17 g, 2 mmol) in 10 ml CH~2~Cl~2~, was added dropwise over 10 min, tert-butyl isocyanide (0.45 g, 2 mmol) in 2 ml CH₂Cl₂ . The mixture was then refluxed for 24 h. The solvent was removed under pressure and the residue was purified by silica gel (Merck 230-400 mesh) column chromatography using n-hexane-diethyl ether (2:3) as eluent. Three products were isolated. The single crystals of the title compound were obtained from the n-hexane-ethyl acetate solution. Orange powder, yield 20%. ¹H NMR (300 MHz, CDCl₃): δ = 1.39 (9H, s, CMe₃), 3.78 (3H, s, OMe), 6.12 (1H, d, ³JHH= 10.0 Hz, S—CH=CH), 7.52 (1H, d, ³JHH = 13.4 Hz, NH—CH=C), 8.41 (1H, d, ³JHH = 10.0 Hz, S—CH=CH), 10.12 (1H, d, ³JHH = 13.4 Hz, NH—CH=C). ¹³CNMR (75.5 MHz, CDCl₃): δ= 29.94 (CMe₃), 51.91 (OCH₃), 53.98 (CMe₃), 96.52 (NH— CH=C), 115.38 (CH=CH—C=O), 139.29 (CH=CH—C=O), 145.10 (NH—CH=C), 166.86 (C=N), 177.42 and 179.48 (2 C=O). IR (KBr) (ν/cm^-1): 3313-3562 (NH), 1699 and 1643 (2 C=O), 1578 (C=N).

Structure description top

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 methods for their synthesis, 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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. The dashed lines show N—H··· O intramolecular interaction.
	Fig. 2. The crystal packing of the title compound viewed down the c-axis showing linking of molecules along the a-axis by the intermolecular C—H···O hydrogen bonds. The dashed lines show intermolecular interactions.

Methyl (Z)-3-({5-[(E)-(tert-butylamino)methylidene]- 4-oxo-4,5-dihydro-1,3-thiazol-2-yl}sulfanyl)prop-2-enoate top

Crystal data top

C₁₂H₁₆N₂O₃S₂	F(000) = 632
M_r = 300.39	D_x = 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

Data collection top

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

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.010P)² + 1.980P] where P = (F_o² + 2F_c²)/3
3939 reflections	(Δ/σ)_max = 0.001
177 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₂H₁₆N₂O₃S₂	V = 1485.9 (10) Å³
M_r = 300.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.011 (2) Å	µ = 0.36 mm⁻¹
b = 19.333 (7) Å	T = 120 K
c = 12.870 (5) Å	0.20 × 0.10 × 0.10 mm
β = 96.502 (8)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3939 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	3125 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.965	R_int = 0.052
15867 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.00	Δρ_max = 0.66 e Å⁻³
3939 reflections	Δρ_min = −0.28 e Å⁻³
177 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 > 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₆N₂O₃S₂
M_r	300.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	6.011 (2), 19.333 (7), 12.870 (5)
β (°)	96.502 (8)
V (Å³)	1485.9 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.951, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	15867, 3939, 3125
R_int	0.052
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.108, 1.00
No. of reflections	3939
No. of parameters	177
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.28

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x+1, y, z.

Acknowledgements

We thank Dr H. Golchoubian for his help with the data collection.

References

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Volume 66| Part 9| September 2010| Pages o2344-o2345

https://doi.org/10.1107/S1600536810030849

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl (Z)-3-({5-[(E)-(tert-butyl­amino)­methyl­­idene]-4-oxo-4,5-di­hydro-1,3-thia­zol-2-yl}sulfan­yl)prop-2-enoate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Methyl (Z)-3-({5-[(E)-(tert-butylamino)methylidene]-4-oxo-4,5-dihydro-1,3-thiazol-2-yl}sulfanyl)prop-2-enoate