N-(Thia-zol-2-yl)acetamide.

The title compound, C(5)H(6)N(2)OS, was synthesized from acetyl chloride and 2-amino-thia-zole in dry acetone. The asymmetric unit contains two mol-ecules. The crystal structure is stabilized by N-H⋯N and C-H⋯O hydrogen bonds.

Related literature

For related literature, see: Raman et al. (2000 ▶); Wang et al. (2008 ▶); Yunus et al. (2007 ▶ 2008 ▶).

Experimental

Crystal data

C5H6N2OS

M = 142.18

Monoclinic,

a = 16.0650 (12) Å

b = 11.3337 (8) Å

c = 7.0670 (5) Å

β = 101.908 (10)°

V = 1259.04 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 173 (2) K

0.30 × 0.26 × 0.22 mm

Data collection

Bruker SMART1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.830, T max = 1.000 (expected range = 0.757–0.911)

7429 measured reflections

3024 independent reflections

2602 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.05

3024 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.34 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808021442/wk2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021442/wk2088Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

C5H6N2OS	F000 = 592
Mr = 142.18	Dx = 1.500 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7429 reflections
a = 16.0650 (12) Å	θ = 2.6–28.3º
b = 11.3337 (8) Å	µ = 0.42 mm−1
c = 7.0670 (5) Å	T = 173 (2) K
β = 101.908 (10)º	Block, pale yellow
V = 1259.04 (16) Å3	0.30 × 0.26 × 0.22 mm
Z = 8

Bruker SMART1000 CCD diffractometer	3024 independent reflections
Radiation source: fine-focus sealed tube	2602 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.024
T = 173(2) K	θmax = 28.3º
ω and φ scans	θmin = 2.6º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −21→18
Tmin = 0.830, Tmax = 1.000	k = −15→12
7429 measured reflections	l = −9→9

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.5928P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3024 reflections	Δρmax = 0.44 e Å−3
163 parameters	Δρmin = −0.34 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
C1	0.22544 (11)	0.26865 (16)	0.3481 (3)	0.0287 (4)
H1A	0.2073	0.1965	0.2843	0.034*
C2	0.17369 (11)	0.35988 (15)	0.3648 (3)	0.0276 (4)
H2A	0.1143	0.3575	0.3127	0.033*
C3	0.29472 (10)	0.43764 (14)	0.5196 (2)	0.0223 (3)
C4	0.43344 (10)	0.50546 (16)	0.6861 (3)	0.0281 (4)
C5	0.48077 (11)	0.61150 (18)	0.7800 (3)	0.0362 (4)
H5A	0.5407	0.5910	0.8272	0.054*
H5B	0.4560	0.6372	0.8887	0.054*
H5C	0.4765	0.6755	0.6852	0.054*
C6	0.28449 (12)	0.53644 (16)	1.0659 (3)	0.0313 (4)
H6A	0.3085	0.4598	1.0867	0.038*
C7	0.32581 (11)	0.63693 (16)	1.1264 (3)	0.0290 (4)
H7A	0.3831	0.6374	1.1960	0.035*
C8	0.20282 (10)	0.71411 (14)	0.9848 (2)	0.0227 (3)
C9	0.06151 (10)	0.78011 (16)	0.8300 (3)	0.0277 (4)
C10	0.00676 (12)	0.88668 (17)	0.7755 (3)	0.0381 (4)
H10A	−0.0506	0.8618	0.7116	0.057*
H10B	0.0312	0.9361	0.6872	0.057*
H10C	0.0038	0.9318	0.8922	0.057*
N1	0.21293 (9)	0.45737 (13)	0.4630 (2)	0.0254 (3)
N2	0.34869 (8)	0.52329 (13)	0.6143 (2)	0.0252 (3)
H2B	0.3273	0.5934	0.6293	0.030*
N3	0.27956 (8)	0.73976 (13)	1.0806 (2)	0.0255 (3)
N4	0.14391 (8)	0.80175 (12)	0.9218 (2)	0.0246 (3)
H4A	0.1602	0.8756	0.9418	0.030*
O1	0.46679 (8)	0.40975 (12)	0.6735 (2)	0.0386 (3)
O2	0.03563 (8)	0.67920 (12)	0.7966 (2)	0.0380 (3)
S1	0.32900 (3)	0.30062 (4)	0.45821 (7)	0.02647 (13)
S2	0.18167 (3)	0.56560 (4)	0.94536 (7)	0.02913 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0280 (8)	0.0239 (8)	0.0334 (9)	−0.0035 (6)	0.0047 (7)	−0.0030 (7)
C2	0.0213 (8)	0.0266 (8)	0.0329 (9)	−0.0019 (6)	0.0008 (6)	−0.0002 (7)
C3	0.0200 (7)	0.0211 (7)	0.0250 (8)	0.0019 (6)	0.0030 (6)	0.0021 (6)
C4	0.0200 (8)	0.0303 (9)	0.0322 (9)	0.0014 (6)	0.0016 (7)	0.0026 (7)
C5	0.0232 (8)	0.0368 (10)	0.0448 (11)	−0.0038 (7)	−0.0015 (7)	−0.0044 (8)
C6	0.0300 (9)	0.0250 (8)	0.0376 (10)	0.0057 (7)	0.0038 (7)	0.0037 (7)
C7	0.0237 (8)	0.0296 (9)	0.0321 (9)	0.0033 (7)	0.0024 (7)	0.0052 (7)
C8	0.0217 (7)	0.0215 (7)	0.0247 (8)	−0.0020 (6)	0.0044 (6)	0.0014 (6)
C9	0.0184 (7)	0.0280 (9)	0.0352 (9)	−0.0010 (6)	0.0021 (6)	0.0005 (7)
C10	0.0240 (8)	0.0327 (10)	0.0540 (12)	0.0040 (7)	−0.0004 (8)	0.0011 (9)
N1	0.0185 (6)	0.0249 (7)	0.0314 (8)	0.0000 (5)	0.0016 (5)	−0.0005 (6)
N2	0.0184 (6)	0.0222 (7)	0.0329 (8)	0.0005 (5)	0.0005 (5)	−0.0019 (6)
N3	0.0200 (6)	0.0242 (7)	0.0305 (8)	−0.0007 (5)	0.0009 (5)	0.0032 (6)
N4	0.0182 (6)	0.0195 (7)	0.0342 (8)	−0.0011 (5)	0.0008 (5)	−0.0003 (5)
O1	0.0232 (6)	0.0317 (7)	0.0557 (9)	0.0058 (5)	−0.0039 (6)	−0.0007 (6)
O2	0.0220 (6)	0.0276 (7)	0.0590 (9)	−0.0047 (5)	−0.0042 (6)	−0.0023 (6)
S1	0.0229 (2)	0.0210 (2)	0.0349 (2)	0.00316 (14)	0.00479 (16)	−0.00010 (15)
S2	0.0261 (2)	0.0205 (2)	0.0385 (3)	−0.00185 (15)	0.00132 (17)	−0.00081 (16)

C1—C2	1.347 (2)	C6—S2	1.7271 (19)
C1—S1	1.7236 (18)	C6—H6A	0.9500
C1—H1A	0.9500	C7—N3	1.384 (2)
C2—N1	1.385 (2)	C7—H7A	0.9500
C2—H2A	0.9500	C8—N3	1.311 (2)
C3—N1	1.311 (2)	C8—N4	1.381 (2)
C3—N2	1.379 (2)	C8—S2	1.7284 (17)
C3—S1	1.7326 (16)	C9—O2	1.223 (2)
C4—O1	1.221 (2)	C9—N4	1.371 (2)
C4—N2	1.366 (2)	C9—C10	1.497 (2)
C4—C5	1.502 (3)	C10—H10A	0.9800
C5—H5A	0.9800	C10—H10B	0.9800
C5—H5B	0.9800	C10—H10C	0.9800
C5—H5C	0.9800	N2—H2B	0.8800
C6—C7	1.343 (3)	N4—H4A	0.8800
C2—C1—S1	110.78 (13)	N3—C7—H7A	122.2
C2—C1—H1A	124.6	N3—C8—N4	121.06 (15)
S1—C1—H1A	124.6	N3—C8—S2	115.59 (12)
C1—C2—N1	115.51 (15)	N4—C8—S2	123.35 (12)
C1—C2—H2A	122.2	O2—C9—N4	121.01 (16)
N1—C2—H2A	122.2	O2—C9—C10	123.13 (16)
N1—C3—N2	121.20 (15)	N4—C9—C10	115.86 (15)
N1—C3—S1	115.26 (12)	C9—C10—H10A	109.5
N2—C3—S1	123.49 (12)	C9—C10—H10B	109.5
O1—C4—N2	121.52 (16)	H10A—C10—H10B	109.5
O1—C4—C5	123.60 (15)	C9—C10—H10C	109.5
N2—C4—C5	114.88 (15)	H10A—C10—H10C	109.5
C4—C5—H5A	109.5	H10B—C10—H10C	109.5
C4—C5—H5B	109.5	C3—N1—C2	109.91 (14)
H5A—C5—H5B	109.5	C4—N2—C3	123.68 (15)
C4—C5—H5C	109.5	C4—N2—H2B	118.2
H5A—C5—H5C	109.5	C3—N2—H2B	118.2
H5B—C5—H5C	109.5	C8—N3—C7	109.65 (15)
C7—C6—S2	110.75 (13)	C9—N4—C8	123.68 (14)
C7—C6—H6A	124.6	C9—N4—H4A	118.2
S2—C6—H6A	124.6	C8—N4—H4A	118.2
C6—C7—N3	115.69 (15)	C1—S1—C3	88.54 (8)
C6—C7—H7A	122.2	C6—S2—C8	88.31 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···N3i	0.88	2.04	2.897 (2)	163
N4—H4A···N1ii	0.88	2.07	2.938 (2)	171
C2—H2A···O2iii	0.95	2.41	3.350 (2)	171
C7—H7A···O1iv	0.95	2.46	3.382 (2)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯N3i	0.88	2.04	2.897 (2)	163
N4—H4A⋯N1ii	0.88	2.07	2.938 (2)	171
C2—H2A⋯O2iii	0.95	2.41	3.350 (2)	171
C7—H7A⋯O1iv	0.95	2.46	3.382 (2)	165

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .