N-(Thia­zol-2-yl)acetamide

Yunus, U.; Tahir, M.K.; Bhatti, M.H.; Wong, W.-Y.

doi:10.1107/S1600536808021442

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1516

doi:10.1107/S1600536808021442

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N-(Thiazol-2-yl)acetamide

Uzma Yunus,^a ^* Muhammad Kalim Tahir,^a Moazzam Hussain Bhatti ^a and Wai-Yeung Wong ^b

^aDepartment of Chemistry, Allama Iqbal Open University, Islamabad, Pakistan, and ^bDepartment of Chemistry, Hong Kong Baptist University, Waterloo Road, Kowloon Tong, Hong Kong
^*Correspondence e-mail: uzma_yunus@yahoo.com

(Received 1 July 2008; accepted 10 July 2008; online 16 July 2008)

The title compound, C₅H₆N₂OS, was synthesized from acetyl chloride and 2-aminothiazole in dry acetone. The asymmetric unit contains two molecules. 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_r = 142.18
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.104
S = 1.05
3024 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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⋯O1^iv	0.95	2.46	3.382 (2)	165
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+2.

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).

Supporting information

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

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

checkCIF report

Comment top

The thiazole ring and its derivatives are of great importance in biological systems due to their vast range of biological activities such as anti-inflammatory, analgesic and antipyretic (Raman et al., 2000). On the other hand amide compounds have extensive applications in the pharmaceutical industry (Wang et al., 2008). As a part of our research the title compound (I) has been synthesized and its crystal structure is reported herein (Yunus et al., 2007; 2008).

The title compound (I) crystallizes in a monoclinic space group with two molecules in asymmetric unit. All the bond lengths and angles are within the normal ranges. The molecules are stabilized by intermolecular hydrogen bonds N—H···N, and C—H···O (Table 1, Fig 2).

Related literature top

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

Experimental top

A mixture of acetyl chloride (26 mmol) and 2-aminothiazole (26 mmol) was refluxed in dry acetone (60 ml) for two hours. After cooling, the mixture was poured into acidified cold water. The resulting yellow solid was filtered and washed with cold acetone. Single crystals of the title compound suitable for single-crystal x-ray analysis were obtained by recrystallization of the yellow solid from ethyl acetate.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); 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).

Figures top

	Fig. 1. The molecular structure of (I) with ellipsoids drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I) showing N—H···N hydrogen bonding.

N-(Thiazol-2-yl)acetamide top

Crystal data top

C₅H₆N₂OS	F(000) = 592
M_r = 142.18	D_x = 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 = 2.6–28.3°
b = 11.3337 (8) Å	µ = 0.42 mm⁻¹
c = 7.0670 (5) Å	T = 173 K
β = 101.908 (10)°	Block, pale yellow
V = 1259.04 (16) Å³	0.30 × 0.26 × 0.22 mm
Z = 8

Data collection top

Bruker SMART1000 CCD diffractometer	3024 independent reflections
Radiation source: fine-focus sealed tube	2602 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω and ϕ scans	θ_max = 28.3°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −21→18
T_min = 0.830, T_max = 1.000	k = −15→12
7429 measured reflections	l = −9→9

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0544P)² + 0.5928P] where P = (F_o² + 2F_c²)/3
3024 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₅H₆N₂OS	V = 1259.04 (16) Å³
M_r = 142.18	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.0650 (12) Å	µ = 0.42 mm⁻¹
b = 11.3337 (8) Å	T = 173 K
c = 7.0670 (5) Å	0.30 × 0.26 × 0.22 mm
β = 101.908 (10)°

Data collection top

Bruker SMART1000 CCD diffractometer	3024 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2602 reflections with I > 2σ(I)
T_min = 0.830, T_max = 1.000	R_int = 0.024
7429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.05	Δρ_max = 0.44 e Å⁻³
3024 reflections	Δρ_min = −0.34 e Å⁻³
163 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.95	2.46	3.382 (2)	165

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

Experimental details

Crystal data
Chemical formula	C₅H₆N₂OS
M_r	142.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	16.0650 (12), 11.3337 (8), 7.0670 (5)
β (°)	101.908 (10)
V (Å³)	1259.04 (16)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.42
Crystal size (mm)	0.30 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.830, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7429, 3024, 2602
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.104, 1.05
No. of reflections	3024
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.34

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.95	2.46	3.382 (2)	165

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

Acknowledgements

The authors gratefully acknowledge Allama Iqbal Open University, Islamabad, Pakistan, for providing research facilities.

References

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