Ethyl 2-amino-4-phenyl-1,3-thia­zole-5-carboxyl­ate

The structure of the title compound, C₁₂H₁₂N₂O₂S, (I), comprises mol­ecules that form dimers via N-H...N hydrogen-bonding interactions and then construct the overall network through N-H...O associations. The dihedral angle between the phenyl and thia­zole rings is 42.41 (6)°.

S1. Comment

NO COMMENT

S2. Experimental

Crystals of (I) obtained from Spa Contract Synthesis.

S3. Refinement

All H atoms were included in the refinement, at calculated positions, as riding models with C—H set to 0.95 (Ar—H), 0.98 (CH₃) and 0.99 Å (CH₂), except for the two amine H atoms which were located on difference syntheses and both the positional and displacement parameters were refined.

Computing details

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

Ethyl-2-amino-4-phenyl-1,3-thiazole-5-carboxylate

Crystal data

C12H12N2O2S	Dx = 1.393 Mg m^−3
Mr = 248.30	Melting point: 443-446 K K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.3124 (2) Å	Cell parameters from 3395 reflections
b = 8.6888 (3) Å	θ = 2.9–27.5°
c = 13.3156 (3) Å	µ = 0.26 mm^−1
β = 97.2427 (15)°	T = 150 K
V = 1183.59 (5) Å^3	Block, colourless
Z = 4	0.20 × 0.15 × 0.15 mm
F(000) = 520

Data collection

Enraf Nonius KappaCCD area-detector diffractometer	2633 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	2361 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ϕ and ω scans	h = −12→12
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −11→11
Tmin = 0.949, Tmax = 0.961	l = −17→17
7275 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0579P)^2 + 0.367P] where P = (Fo^2 + 2Fc^2)/3
2633 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

Special details

Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.

Geometry. Mean plane data ex SHELXL97 ###########################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

6.9415 (0.0041) x − 4.4815 (0.0048) y + 5.8707 (0.0051) z = 5.8341 (0.0050)

* 0.0083 (0.0006) S1 * −0.0116 (0.0007) C2 * 0.0095 (0.0008) N3 * −0.0051 (0.0007) C4 * −0.0012 (0.0008) C5

Rms deviation of fitted atoms = 0.0080

0.1343 (0.0062) x − 6.9936 (0.0031) y + 7.8148 (0.0064) z = 5.8468 (0.0089)

Angle to previous plane (with approximate e.s.d.) = 42.41 (0.06)

* −0.0133 (0.0009) C51 * 0.0109 (0.0010) C52 * 0.0006 (0.0011) C53 * −0.0097 (0.0011) C54 * 0.0070 (0.0011) C55 * 0.0044 (0.0010) C56

Rms deviation of fitted atoms = 0.0087

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.24807 (3)	0.18693 (4)	0.84455 (2)	0.02280 (13)
C2	0.13295 (13)	0.09723 (16)	0.90882 (10)	0.0218 (3)
N21	0.07800 (13)	−0.03581 (15)	0.87752 (10)	0.0282 (3)
H21	0.021 (2)	−0.078 (3)	0.9142 (15)	0.045 (5)*
H22	0.0804 (18)	−0.064 (2)	0.8175 (15)	0.036 (5)*
N3	0.11005 (11)	0.16755 (13)	0.99316 (8)	0.0211 (3)
C4	0.26216 (13)	0.33128 (15)	0.93581 (10)	0.0203 (3)
C41	0.33249 (12)	0.46830 (16)	0.91062 (9)	0.0212 (3)
O40	0.39483 (10)	0.47402 (13)	0.83881 (7)	0.0295 (3)
O41	0.31899 (10)	0.58702 (12)	0.97100 (8)	0.0286 (2)
C42	0.38210 (15)	0.73012 (18)	0.94991 (11)	0.0290 (3)
H421	0.3399	0.7754	0.8858	0.036*
H422	0.4757	0.7126	0.9440	0.036*
C43	0.36748 (19)	0.83485 (19)	1.03686 (13)	0.0378 (4)
H431	0.2748	0.8440	1.0453	0.047*
H432	0.4024	0.9367	1.0235	0.047*
H433	0.4157	0.7925	1.0988	0.047*
C5	0.18140 (12)	0.30015 (15)	1.00820 (9)	0.0187 (3)
C51	0.16088 (13)	0.39469 (15)	1.09692 (9)	0.0195 (3)
C52	0.26394 (13)	0.46232 (17)	1.15876 (9)	0.0239 (3)
H52	0.3512	0.4457	1.1454	0.030*
C53	0.24025 (15)	0.55370 (19)	1.23964 (11)	0.0303 (3)
H53	0.3111	0.6010	1.2808	0.038*
C54	0.11377 (15)	0.57624 (19)	1.26067 (11)	0.0309 (3)
H54	0.0976	0.6401	1.3157	0.039*
C55	0.01093 (14)	0.50597 (18)	1.20168 (10)	0.0267 (3)
H55	−0.0758	0.5197	1.2171	0.033*
C56	0.03374 (13)	0.41541 (16)	1.11991 (10)	0.0225 (3)
H56	−0.0374	0.3674	1.0795	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0254 (2)	0.0238 (2)	0.02088 (19)	−0.00260 (12)	0.00964 (13)	−0.00198 (12)
C2	0.0227 (7)	0.0233 (7)	0.0202 (6)	−0.0009 (5)	0.0056 (5)	0.0008 (5)
N21	0.0367 (7)	0.0279 (7)	0.0222 (6)	−0.0103 (5)	0.0119 (5)	−0.0061 (5)
N3	0.0230 (6)	0.0223 (6)	0.0190 (5)	−0.0028 (4)	0.0061 (4)	−0.0007 (4)
C4	0.0211 (7)	0.0221 (7)	0.0183 (6)	−0.0008 (5)	0.0047 (5)	−0.0007 (5)
C41	0.0187 (6)	0.0251 (7)	0.0199 (6)	−0.0013 (5)	0.0033 (5)	0.0014 (5)
O40	0.0345 (6)	0.0313 (6)	0.0256 (5)	−0.0049 (4)	0.0149 (4)	0.0012 (4)
O41	0.0357 (6)	0.0228 (5)	0.0300 (5)	−0.0098 (4)	0.0149 (4)	−0.0028 (4)
C42	0.0337 (8)	0.0230 (7)	0.0309 (7)	−0.0083 (6)	0.0068 (6)	0.0033 (6)
C43	0.0485 (10)	0.0276 (8)	0.0373 (9)	−0.0093 (7)	0.0050 (7)	−0.0040 (7)
C5	0.0177 (6)	0.0208 (7)	0.0179 (6)	−0.0002 (5)	0.0030 (5)	0.0018 (5)
C51	0.0228 (7)	0.0188 (6)	0.0175 (6)	−0.0004 (5)	0.0055 (5)	0.0027 (5)
C52	0.0221 (7)	0.0284 (8)	0.0215 (6)	−0.0014 (5)	0.0045 (5)	−0.0007 (5)
C53	0.0322 (8)	0.0342 (8)	0.0243 (7)	−0.0038 (6)	0.0030 (5)	−0.0064 (6)
C54	0.0402 (8)	0.0308 (8)	0.0231 (7)	0.0022 (6)	0.0094 (6)	−0.0048 (6)
C55	0.0264 (7)	0.0297 (8)	0.0258 (7)	0.0048 (6)	0.0108 (5)	0.0019 (6)
C56	0.0228 (7)	0.0234 (7)	0.0216 (6)	0.0000 (5)	0.0045 (5)	0.0026 (5)

Geometric parameters (Å, º)

S1—C2	1.7336 (14)	C43—H431	0.9800
S1—C4	1.7396 (13)	C43—H432	0.9800
C2—N3	1.3256 (17)	C43—H433	0.9800
C2—N21	1.3310 (19)	C5—C51	1.4758 (18)
N21—H21	0.89 (2)	C51—C52	1.3900 (18)
N21—H22	0.838 (19)	C51—C56	1.3952 (19)
N3—C5	1.3681 (18)	C52—C53	1.384 (2)
C4—C5	1.3779 (18)	C52—H52	0.9500
C4—C41	1.4550 (19)	C53—C54	1.382 (2)
C41—O40	1.2188 (16)	C53—H53	0.9500
C41—O41	1.3259 (17)	C54—C55	1.380 (2)
O41—C42	1.4472 (17)	C54—H54	0.9500
C42—C43	1.495 (2)	C55—C56	1.387 (2)
C42—H421	0.9900	C55—H55	0.9500
C42—H422	0.9900	C56—H56	0.9500
C2—S1—C4	88.94 (6)	C42—C43—H433	109.5
N3—C2—N21	123.46 (12)	H431—C43—H433	109.5
N3—C2—S1	114.65 (10)	H432—C43—H433	109.5
N21—C2—S1	121.79 (10)	N3—C5—C4	115.10 (12)
C2—N21—H21	118.3 (14)	N3—C5—C51	117.21 (11)
C2—N21—H22	119.1 (13)	C4—C5—C51	127.66 (12)
H21—N21—H22	120.2 (19)	C52—C51—C56	119.01 (12)
C2—N3—C5	111.24 (11)	C52—C51—C5	122.24 (12)
C5—C4—C41	133.21 (13)	C56—C51—C5	118.75 (12)
C5—C4—S1	110.03 (10)	C53—C52—C51	120.44 (13)
C41—C4—S1	115.41 (9)	C53—C52—H52	119.8
O40—C41—O41	123.37 (13)	C51—C52—H52	119.8
O40—C41—C4	122.80 (13)	C54—C53—C52	120.17 (14)
O41—C41—C4	113.79 (11)	C54—C53—H53	119.9
C41—O41—C42	117.82 (11)	C52—C53—H53	119.9
O41—C42—C43	106.32 (12)	C55—C54—C53	119.94 (13)
O41—C42—H421	110.5	C55—C54—H54	120.0
C43—C42—H421	110.5	C53—C54—H54	120.0
O41—C42—H422	110.5	C54—C55—C56	120.23 (13)
C43—C42—H422	110.5	C54—C55—H55	119.9
H421—C42—H422	108.7	C56—C55—H55	119.9
C42—C43—H431	109.5	C55—C56—C51	120.16 (13)
C42—C43—H432	109.5	C55—C56—H56	119.9
H431—C43—H432	109.5	C51—C56—H56	119.9
C4—S1—C2—N3	−1.73 (11)	S1—C4—C5—N3	−0.11 (15)
C4—S1—C2—N21	−178.45 (12)	C41—C4—C5—C51	−12.5 (2)
N21—C2—N3—C5	178.63 (13)	S1—C4—C5—C51	−178.18 (11)
S1—C2—N3—C5	1.98 (15)	N3—C5—C51—C52	137.62 (13)
C2—S1—C4—C5	0.98 (10)	C4—C5—C51—C52	−44.3 (2)
C2—S1—C4—C41	−167.54 (11)	N3—C5—C51—C56	−41.71 (17)
C5—C4—C41—O40	−176.12 (14)	C4—C5—C51—C56	136.33 (14)
S1—C4—C41—O40	−10.98 (18)	C56—C51—C52—C53	−2.5 (2)
C5—C4—C41—O41	1.9 (2)	C5—C51—C52—C53	178.20 (13)
S1—C4—C41—O41	167.04 (9)	C51—C52—C53—C54	1.2 (2)
O40—C41—O41—C42	−0.1 (2)	C52—C53—C54—C55	0.8 (2)
C4—C41—O41—C42	−178.10 (12)	C53—C54—C55—C56	−1.4 (2)
C41—O41—C42—C43	−171.97 (13)	C54—C55—C56—C51	0.1 (2)
C2—N3—C5—C4	−1.19 (17)	C52—C51—C56—C55	1.8 (2)
C2—N3—C5—C51	177.10 (11)	C5—C51—C56—C55	−178.80 (12)
C41—C4—C5—N3	165.62 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21···N3^i	0.89 (2)	2.09 (2)	2.9797 (17)	176.4 (19)
N21—H22···O40^ii	0.838 (19)	2.15 (2)	2.9302 (16)	154.0 (18)

Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1/2, y−1/2, −z+3/2.