Ethyl 2-[(tert-but-oxy-carbon-yl)amino]-thia-zole-5-carboxyl-ate.

In the crystal of the title compound, C(11)H(16)N(2)O(4)S, molecules are linked via pairs of N-H⋯N hydrogen bonds to form inversion dimers. The dimers are linked by a weak C-H⋯O interaction to form chains propagating along direction [100].

Related literature

For details of the synthesis, see: Upadhyaya et al. (2007 ▶). For the bioactivity of thia­zoles, see: Barradas et al. (2011 ▶); Zaharia et al. (2010 ▶). For related structures, see: Liu et al. (2011 ▶); Wang (2011 ▶).

Experimental

Crystal data

C11H16N2O4S

M = 272.32

Monoclinic,

a = 5.8258 (12) Å

b = 9.4916 (19) Å

c = 24.350 (5) Å

β = 92.37 (3)°

V = 1345.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 113 K

0.26 × 0.24 × 0.22 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan CrystalClear (Rigaku, 2005 ▶) T min = 0.938, T max = 0.947

11392 measured reflections

3180 independent reflections

2177 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.155

S = 1.07

3180 reflections

172 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.46 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: CrystalStructure (Rigaku, 2005 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005971/ff2055sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005971/ff2055Isup4.hkl

Supplementary material file. DOI: 10.1107/S1600536812005971/ff2055Isup3.cml

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

C11H16N2O4S	F(000) = 576
Mr = 272.32	Dx = 1.345 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.8258 (12) Å	Cell parameters from 2589 reflections
b = 9.4916 (19) Å	θ = 2.3–28.0°
c = 24.350 (5) Å	µ = 0.25 mm−1
β = 92.37 (3)°	T = 113 K
V = 1345.3 (5) Å3	Block, colourless
Z = 4	0.26 × 0.24 × 0.22 mm

Rigaku Saturn CCD diffractometer	3180 independent reflections
Radiation source: rotating anode	2177 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.057
Detector resolution: 7.31 pixels mm-1	θmax = 28.0°, θmin = 2.3°
ω and φ scans	h = −7→7
Absorption correction: multi-scan CrystalClear (Rigaku, 2005)	k = −12→12
Tmin = 0.938, Tmax = 0.947	l = −32→30
11392 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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.155	w = 1/[σ2(Fo2) + (0.0806P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3180 reflections	Δρmax = 0.46 e Å−3
172 parameters	Δρmin = −0.46 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: 0.014 (4)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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	0.48801 (9)	0.74851 (5)	0.499500 (19)	0.0218 (2)
O1	0.4912 (3)	0.86694 (18)	0.65493 (6)	0.0358 (4)
O2	0.2511 (3)	0.91136 (16)	0.58203 (6)	0.0277 (4)
O3	0.5169 (3)	0.68642 (17)	0.39011 (6)	0.0287 (4)
O4	0.7506 (3)	0.51367 (14)	0.35826 (6)	0.0211 (4)
N1	0.8382 (3)	0.60995 (19)	0.54014 (7)	0.0240 (4)
N2	0.7723 (3)	0.5693 (2)	0.44654 (7)	0.0229 (4)
C1	0.7172 (4)	0.6345 (2)	0.49427 (9)	0.0211 (5)
C2	0.7472 (4)	0.6836 (2)	0.58220 (9)	0.0251 (5)
H2	0.8121	0.6796	0.6186	0.030*
C3	0.5600 (4)	0.7625 (2)	0.56921 (8)	0.0217 (5)
C4	0.4342 (4)	0.8514 (2)	0.60725 (9)	0.0257 (5)
C5	0.1173 (5)	1.0034 (3)	0.61617 (11)	0.0347 (6)
H5A	0.2188	1.0727	0.6355	0.042*
H5B	0.0377	0.9476	0.6440	0.042*
C6	−0.0552 (4)	1.0780 (3)	0.57876 (11)	0.0353 (6)
H6A	0.0257	1.1341	0.5518	0.053*
H6B	−0.1502	1.1402	0.6005	0.053*
H6C	−0.1532	1.0084	0.5595	0.053*
C7	0.6642 (4)	0.5978 (2)	0.39667 (9)	0.0222 (5)
C8	0.6805 (4)	0.5341 (2)	0.29934 (8)	0.0203 (5)
C9	0.4230 (4)	0.5149 (2)	0.29012 (10)	0.0253 (5)
H9A	0.3779	0.4226	0.3042	0.038*
H9B	0.3828	0.5204	0.2507	0.038*
H9C	0.3423	0.5892	0.3095	0.038*
C10	0.7627 (4)	0.6774 (2)	0.28086 (10)	0.0295 (5)
H10A	0.6756	0.7513	0.2989	0.044*
H10B	0.7391	0.6857	0.2409	0.044*
H10C	0.9265	0.6879	0.2909	0.044*
C11	0.8063 (4)	0.4163 (2)	0.27124 (9)	0.0257 (5)
H11A	0.9718	0.4255	0.2793	0.039*
H11B	0.7752	0.4220	0.2314	0.039*
H11C	0.7531	0.3252	0.2848	0.039*
H2A	0.881 (5)	0.512 (3)	0.4476 (13)	0.047 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0254 (3)	0.0232 (3)	0.0166 (3)	0.0059 (2)	−0.0008 (2)	−0.0012 (2)
O1	0.0432 (11)	0.0404 (10)	0.0237 (9)	0.0136 (8)	−0.0007 (7)	−0.0049 (8)
O2	0.0284 (9)	0.0279 (9)	0.0267 (9)	0.0098 (7)	−0.0011 (6)	−0.0062 (7)
O3	0.0319 (9)	0.0309 (9)	0.0231 (8)	0.0136 (7)	−0.0018 (6)	−0.0013 (7)
O4	0.0237 (8)	0.0235 (8)	0.0161 (8)	0.0064 (6)	−0.0018 (6)	−0.0022 (6)
N1	0.0288 (10)	0.0242 (10)	0.0188 (9)	0.0043 (8)	−0.0004 (7)	0.0005 (7)
N2	0.0262 (10)	0.0241 (10)	0.0182 (9)	0.0082 (8)	−0.0007 (7)	−0.0010 (7)
C1	0.0236 (11)	0.0178 (11)	0.0219 (11)	0.0005 (9)	0.0019 (8)	−0.0002 (8)
C2	0.0302 (12)	0.0247 (12)	0.0202 (11)	0.0027 (9)	0.0010 (8)	−0.0003 (9)
C3	0.0257 (11)	0.0208 (11)	0.0185 (10)	0.0001 (9)	−0.0005 (8)	−0.0014 (8)
C4	0.0296 (12)	0.0230 (12)	0.0246 (12)	0.0013 (10)	0.0033 (9)	−0.0007 (9)
C5	0.0353 (14)	0.0347 (14)	0.0342 (15)	0.0132 (11)	0.0041 (11)	−0.0099 (11)
C6	0.0294 (13)	0.0291 (13)	0.0478 (16)	0.0058 (10)	0.0052 (11)	−0.0024 (12)
C7	0.0241 (11)	0.0204 (11)	0.0221 (11)	0.0022 (9)	0.0018 (8)	−0.0011 (9)
C8	0.0221 (11)	0.0246 (11)	0.0140 (10)	0.0005 (9)	−0.0005 (8)	−0.0004 (8)
C9	0.0205 (11)	0.0318 (13)	0.0233 (12)	−0.0004 (9)	−0.0018 (9)	0.0000 (9)
C10	0.0326 (13)	0.0258 (13)	0.0299 (12)	−0.0068 (10)	−0.0027 (9)	0.0015 (10)
C11	0.0231 (12)	0.0313 (13)	0.0228 (11)	0.0028 (9)	0.0029 (8)	−0.0080 (9)

S1—C1	1.727 (2)	C5—H5A	0.9900
S1—C3	1.737 (2)	C5—H5B	0.9900
O1—C4	1.204 (3)	C6—H6A	0.9800
O2—C4	1.336 (3)	C6—H6B	0.9800
O2—C5	1.455 (3)	C6—H6C	0.9800
O3—C7	1.208 (2)	C8—C11	1.515 (3)
O4—C7	1.343 (2)	C8—C10	1.517 (3)
O4—C8	1.488 (2)	C8—C9	1.518 (3)
N1—C1	1.317 (3)	C9—H9A	0.9800
N1—C2	1.365 (3)	C9—H9B	0.9800
N2—C1	1.367 (3)	C9—H9C	0.9800
N2—C7	1.371 (3)	C10—H10A	0.9800
N2—H2A	0.84 (3)	C10—H10B	0.9800
C2—C3	1.349 (3)	C10—H10C	0.9800
C2—H2	0.9500	C11—H11A	0.9800
C3—C4	1.471 (3)	C11—H11B	0.9800
C5—C6	1.505 (4)	C11—H11C	0.9800
C1—S1—C3	87.93 (10)	H6A—C6—H6C	109.5
C4—O2—C5	115.48 (18)	H6B—C6—H6C	109.5
C7—O4—C8	119.88 (16)	O3—C7—O4	127.3 (2)
C1—N1—C2	109.57 (18)	O3—C7—N2	123.5 (2)
C1—N2—C7	123.24 (19)	O4—C7—N2	109.13 (18)
C1—N2—H2A	118 (2)	O4—C8—C11	102.75 (16)
C7—N2—H2A	119 (2)	O4—C8—C10	108.99 (17)
N1—C1—N2	120.32 (19)	C11—C8—C10	111.31 (18)
N1—C1—S1	115.88 (16)	O4—C8—C9	110.91 (17)
N2—C1—S1	123.78 (16)	C11—C8—C9	109.73 (18)
C3—C2—N1	116.31 (19)	C10—C8—C9	112.70 (18)
C3—C2—H2	121.8	C8—C9—H9A	109.5
N1—C2—H2	121.8	C8—C9—H9B	109.5
C2—C3—C4	126.1 (2)	H9A—C9—H9B	109.5
C2—C3—S1	110.30 (16)	C8—C9—H9C	109.5
C4—C3—S1	123.57 (16)	H9A—C9—H9C	109.5
O1—C4—O2	125.0 (2)	H9B—C9—H9C	109.5
O1—C4—C3	123.6 (2)	C8—C10—H10A	109.5
O2—C4—C3	111.36 (19)	C8—C10—H10B	109.5
O2—C5—C6	107.3 (2)	H10A—C10—H10B	109.5
O2—C5—H5A	110.3	C8—C10—H10C	109.5
C6—C5—H5A	110.3	H10A—C10—H10C	109.5
O2—C5—H5B	110.3	H10B—C10—H10C	109.5
C6—C5—H5B	110.3	C8—C11—H11A	109.5
H5A—C5—H5B	108.5	C8—C11—H11B	109.5
C5—C6—H6A	109.5	H11A—C11—H11B	109.5
C5—C6—H6B	109.5	C8—C11—H11C	109.5
H6A—C6—H6B	109.5	H11A—C11—H11C	109.5
C5—C6—H6C	109.5	H11B—C11—H11C	109.5
C2—N1—C1—N2	−178.4 (2)	C2—C3—C4—O1	2.5 (4)
C2—N1—C1—S1	0.3 (2)	S1—C3—C4—O1	−175.89 (19)
C7—N2—C1—N1	−175.1 (2)	C2—C3—C4—O2	−177.5 (2)
C7—N2—C1—S1	6.3 (3)	S1—C3—C4—O2	4.1 (3)
C3—S1—C1—N1	−0.62 (17)	C4—O2—C5—C6	170.96 (19)
C3—S1—C1—N2	178.0 (2)	C8—O4—C7—O3	6.0 (3)
C1—N1—C2—C3	0.3 (3)	C8—O4—C7—N2	−173.39 (17)
N1—C2—C3—C4	−179.4 (2)	C1—N2—C7—O3	2.8 (4)
N1—C2—C3—S1	−0.8 (3)	C1—N2—C7—O4	−177.82 (18)
C1—S1—C3—C2	0.74 (17)	C7—O4—C8—C11	−177.64 (17)
C1—S1—C3—C4	179.4 (2)	C7—O4—C8—C10	64.2 (2)
C5—O2—C4—O1	1.0 (3)	C7—O4—C8—C9	−60.4 (2)
C5—O2—C4—C3	−179.05 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.84 (3)	2.01 (3)	2.844 (3)	172 (3)
C10—H10B···O1ii	0.98	2.54	3.418 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.84 (3)	2.01 (3)	2.844 (3)	172 (3)
C10—H10B⋯O1ii	0.98	2.54	3.418 (3)	149

Symmetry codes: (i) ; (ii) .