N-(1,3-Benzo-thia-zol-2-yl)acetamide.

The title compound, C9H8N2OS, crystallizes with two mol-ecules (A and B) in the asymmetric unit. The dihedral angles between the mean planes of the 1,3-benzo-thia-zol-2-yl ring system and the acetamide group are 2.7 (4) (mol-ecule A) and 7.2 (2) Å (mol-ecule B). In the crystal, pairs of N-H⋯N hydrogen bonds link the A and B mol-ecules into dimers, generating R 2 (2)(8) loops. The dimers stack along [100].

Related literature

For the related crystal structure of the acetamide derivatives, see: Jasinski et al. (2013 ▶); Fun et al. (2011a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C9H8N2OS

M = 192.24

Monoclinic,

a = 11.1852 (4) Å

b = 7.4037 (4) Å

c = 20.9189 (8) Å

β = 94.408 (3)°

V = 1727.21 (13) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 173 K

0.45 × 0.24 × 0.15 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ▶)T min = 0.770, T max = 1.000

20845 measured reflections

5918 independent reflections

4622 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.109

S = 1.08

5918 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012 ▶); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S160053681302730X/hb7144sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681302730X/hb7144Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681302730X/hb7144Isup3.cml

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

C9H8N2OS	Dx = 1.479 Mg m−3
Mr = 192.24	Melting point: 453 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.1852 (4) Å	Cell parameters from 5326 reflections
b = 7.4037 (4) Å	θ = 3.3–32.7°
c = 20.9189 (8) Å	µ = 0.33 mm−1
β = 94.408 (3)°	T = 173 K
V = 1727.21 (13) Å3	Block, colorless
Z = 8	0.45 × 0.24 × 0.15 mm
F(000) = 800

Agilent Xcalibur (Eos, Gemini) diffractometer	5918 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4622 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm-1	Rint = 0.033
ω scans	θmax = 32.8°, θmin = 3.3°
Absorption correction: multi-scan CrysAlis PRO and CrysAlis RED, Agilent (2012).	h = −16→16
Tmin = 0.770, Tmax = 1.000	k = −10→9
20845 measured reflections	l = −30→31

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.045P)2 + 0.4973P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
5918 reflections	Δρmax = 0.44 e Å−3
237 parameters	Δρmin = −0.26 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
S1A	0.38148 (3)	0.72688 (5)	0.50197 (2)	0.02464 (9)
O1A	0.45185 (9)	0.64286 (18)	0.62295 (5)	0.0349 (3)
N1A	0.58652 (10)	0.79642 (18)	0.45587 (5)	0.0242 (2)
N2A	0.60552 (10)	0.72112 (17)	0.56435 (5)	0.0232 (2)
H2A	0.6815	0.7393	0.5650	0.028*
C1A	0.53676 (11)	0.75086 (19)	0.50776 (6)	0.0208 (3)
C2A	0.49856 (11)	0.8192 (2)	0.40579 (6)	0.0228 (3)
C3A	0.51887 (13)	0.8704 (2)	0.34317 (7)	0.0301 (3)
H3A	0.5961	0.8949	0.3320	0.036*
C4A	0.42227 (14)	0.8841 (2)	0.29819 (7)	0.0315 (3)
H4A	0.4349	0.9165	0.2563	0.038*
C5A	0.30593 (13)	0.8500 (2)	0.31478 (7)	0.0303 (3)
H5A	0.2423	0.8596	0.2837	0.036*
C6A	0.28360 (13)	0.8024 (2)	0.37647 (7)	0.0284 (3)
H6A	0.2059	0.7813	0.3876	0.034*
C7A	0.38110 (12)	0.7869 (2)	0.42159 (6)	0.0225 (3)
C8A	0.55898 (12)	0.6640 (2)	0.61966 (6)	0.0241 (3)
C9A	0.64887 (14)	0.6310 (2)	0.67511 (7)	0.0312 (3)
H9AA	0.7267	0.6141	0.6597	0.047*
H9AB	0.6268	0.5247	0.6977	0.047*
H9AC	0.6508	0.7329	0.7035	0.047*
S1B	1.06929 (3)	0.76516 (5)	0.50481 (2)	0.02415 (9)
O1B	0.99661 (9)	0.63954 (18)	0.38920 (5)	0.0338 (3)
N1B	0.86730 (10)	0.77933 (17)	0.55907 (5)	0.0230 (2)
N2B	0.84393 (10)	0.70106 (17)	0.45051 (5)	0.0232 (2)
H2B	0.7673	0.7064	0.4517	0.028*
C1B	0.91433 (11)	0.74614 (19)	0.50500 (6)	0.0200 (2)
C2B	0.95787 (11)	0.8261 (2)	0.60567 (6)	0.0210 (3)
C3B	0.94173 (13)	0.8677 (2)	0.66959 (7)	0.0288 (3)
H3B	0.8654	0.8664	0.6844	0.035*
C4B	1.04033 (14)	0.9107 (2)	0.71058 (7)	0.0316 (3)
H4B	1.0302	0.9376	0.7533	0.038*
C5B	1.15469 (13)	0.9140 (2)	0.68865 (7)	0.0303 (3)
H5B	1.2198	0.9446	0.7169	0.036*
C6B	1.17329 (12)	0.8727 (2)	0.62580 (7)	0.0273 (3)
H6B	1.2499	0.8745	0.6114	0.033*
C7B	1.07368 (11)	0.8283 (2)	0.58475 (6)	0.0219 (3)
C8B	0.88922 (12)	0.6480 (2)	0.39429 (6)	0.0242 (3)
C9B	0.79789 (13)	0.5998 (2)	0.34107 (7)	0.0300 (3)
H9BA	0.7214	0.5827	0.3581	0.045*
H9BB	0.8214	0.4902	0.3210	0.045*
H9BC	0.7922	0.6954	0.3100	0.045*

	U11	U22	U33	U12	U13	U23
S1A	0.01604 (15)	0.0370 (2)	0.02094 (15)	−0.00082 (13)	0.00206 (11)	0.00004 (13)
O1A	0.0235 (5)	0.0539 (8)	0.0277 (5)	−0.0055 (5)	0.0038 (4)	0.0070 (5)
N1A	0.0172 (5)	0.0334 (7)	0.0218 (5)	−0.0006 (4)	0.0010 (4)	0.0034 (5)
N2A	0.0165 (5)	0.0327 (7)	0.0203 (5)	−0.0008 (4)	0.0007 (4)	0.0012 (5)
C1A	0.0166 (5)	0.0248 (7)	0.0211 (6)	0.0002 (5)	0.0012 (4)	−0.0005 (5)
C2A	0.0187 (6)	0.0268 (7)	0.0226 (6)	0.0007 (5)	0.0003 (5)	0.0013 (5)
C3A	0.0244 (7)	0.0408 (9)	0.0253 (7)	0.0003 (6)	0.0038 (5)	0.0061 (6)
C4A	0.0329 (8)	0.0394 (9)	0.0222 (6)	0.0038 (6)	0.0014 (5)	0.0054 (6)
C5A	0.0278 (7)	0.0382 (9)	0.0239 (6)	0.0065 (6)	−0.0045 (5)	−0.0010 (6)
C6A	0.0201 (6)	0.0391 (9)	0.0256 (6)	0.0033 (6)	−0.0010 (5)	−0.0024 (6)
C7A	0.0192 (6)	0.0273 (7)	0.0210 (6)	0.0017 (5)	0.0015 (4)	−0.0012 (5)
C8A	0.0243 (6)	0.0273 (7)	0.0206 (6)	−0.0008 (5)	0.0015 (5)	−0.0001 (5)
C9A	0.0303 (7)	0.0387 (9)	0.0240 (7)	0.0007 (6)	−0.0016 (5)	0.0046 (6)
S1B	0.01533 (15)	0.0370 (2)	0.02013 (15)	−0.00067 (12)	0.00165 (11)	−0.00226 (13)
O1B	0.0229 (5)	0.0521 (8)	0.0269 (5)	−0.0017 (5)	0.0051 (4)	−0.0072 (5)
N1B	0.0174 (5)	0.0326 (7)	0.0190 (5)	0.0015 (4)	0.0010 (4)	−0.0006 (4)
N2B	0.0154 (5)	0.0346 (7)	0.0193 (5)	−0.0008 (4)	−0.0010 (4)	−0.0007 (5)
C1B	0.0154 (5)	0.0247 (7)	0.0199 (5)	0.0008 (4)	0.0002 (4)	0.0008 (5)
C2B	0.0181 (6)	0.0251 (7)	0.0194 (6)	0.0021 (5)	−0.0005 (4)	0.0006 (5)
C3B	0.0244 (7)	0.0398 (9)	0.0223 (6)	0.0002 (6)	0.0030 (5)	−0.0037 (6)
C4B	0.0332 (8)	0.0413 (9)	0.0200 (6)	−0.0007 (6)	−0.0002 (5)	−0.0040 (6)
C5B	0.0277 (7)	0.0366 (9)	0.0252 (7)	−0.0039 (6)	−0.0065 (5)	−0.0018 (6)
C6B	0.0194 (6)	0.0369 (9)	0.0249 (6)	−0.0025 (5)	−0.0020 (5)	−0.0010 (6)
C7B	0.0191 (6)	0.0255 (7)	0.0209 (6)	0.0006 (5)	0.0001 (4)	0.0006 (5)
C8B	0.0226 (6)	0.0297 (8)	0.0203 (6)	−0.0026 (5)	0.0010 (5)	−0.0004 (5)
C9B	0.0310 (7)	0.0377 (9)	0.0208 (6)	−0.0051 (6)	−0.0014 (5)	−0.0038 (6)

S1A—C1A	1.7407 (13)	S1B—C1B	1.7392 (13)
S1A—C7A	1.7390 (14)	S1B—C7B	1.7333 (13)
O1A—C8A	1.2156 (17)	O1B—C8B	1.2157 (16)
N1A—C1A	1.3018 (17)	N1B—C1B	1.3068 (16)
N1A—C2A	1.3913 (17)	N1B—C2B	1.3945 (17)
N2A—H2A	0.8600	N2B—H2B	0.8600
N2A—C1A	1.3791 (17)	N2B—C1B	1.3757 (16)
N2A—C8A	1.3715 (17)	N2B—C8B	1.3733 (17)
C2A—C3A	1.3989 (19)	C2B—C3B	1.3974 (18)
C2A—C7A	1.3997 (18)	C2B—C7B	1.3988 (18)
C3A—H3A	0.9300	C3B—H3B	0.9300
C3A—C4A	1.381 (2)	C3B—C4B	1.381 (2)
C4A—H4A	0.9300	C4B—H4B	0.9300
C4A—C5A	1.395 (2)	C4B—C5B	1.392 (2)
C5A—H5A	0.9300	C5B—H5B	0.9300
C5A—C6A	1.379 (2)	C5B—C6B	1.381 (2)
C6A—H6A	0.9300	C6B—H6B	0.9300
C6A—C7A	1.3910 (19)	C6B—C7B	1.3928 (18)
C8A—C9A	1.4957 (19)	C8B—C9B	1.4952 (19)
C9A—H9AA	0.9600	C9B—H9BA	0.9600
C9A—H9AB	0.9600	C9B—H9BB	0.9600
C9A—H9AC	0.9600	C9B—H9BC	0.9600
C7A—S1A—C1A	88.25 (6)	C7B—S1B—C1B	88.51 (6)
C1A—N1A—C2A	109.66 (11)	C1B—N1B—C2B	109.42 (11)
C1A—N2A—H2A	118.3	C1B—N2B—H2B	118.2
C8A—N2A—H2A	118.3	C8B—N2B—H2B	118.2
C8A—N2A—C1A	123.41 (12)	C8B—N2B—C1B	123.62 (11)
N1A—C1A—S1A	117.17 (10)	N1B—C1B—S1B	117.01 (10)
N1A—C1A—N2A	120.74 (12)	N1B—C1B—N2B	121.32 (12)
N2A—C1A—S1A	122.08 (10)	N2B—C1B—S1B	121.66 (10)
N1A—C2A—C3A	125.57 (12)	N1B—C2B—C3B	125.69 (12)
N1A—C2A—C7A	115.07 (12)	N1B—C2B—C7B	115.13 (11)
C3A—C2A—C7A	119.36 (12)	C3B—C2B—C7B	119.18 (12)
C2A—C3A—H3A	120.6	C2B—C3B—H3B	120.4
C4A—C3A—C2A	118.89 (13)	C4B—C3B—C2B	119.29 (13)
C4A—C3A—H3A	120.6	C4B—C3B—H3B	120.4
C3A—C4A—H4A	119.6	C3B—C4B—H4B	119.7
C3A—C4A—C5A	120.87 (13)	C3B—C4B—C5B	120.63 (13)
C5A—C4A—H4A	119.6	C5B—C4B—H4B	119.7
C4A—C5A—H5A	119.4	C4B—C5B—H5B	119.4
C6A—C5A—C4A	121.23 (13)	C6B—C5B—C4B	121.29 (13)
C6A—C5A—H5A	119.4	C6B—C5B—H5B	119.4
C5A—C6A—H6A	121.1	C5B—C6B—H6B	121.1
C5A—C6A—C7A	117.84 (13)	C5B—C6B—C7B	117.86 (13)
C7A—C6A—H6A	121.1	C7B—C6B—H6B	121.1
C2A—C7A—S1A	109.84 (10)	C2B—C7B—S1B	109.90 (10)
C6A—C7A—S1A	128.36 (11)	C6B—C7B—S1B	128.35 (10)
C6A—C7A—C2A	121.80 (12)	C6B—C7B—C2B	121.74 (12)
O1A—C8A—N2A	121.82 (13)	O1B—C8B—N2B	121.45 (12)
O1A—C8A—C9A	122.81 (13)	O1B—C8B—C9B	123.07 (13)
N2A—C8A—C9A	115.37 (12)	N2B—C8B—C9B	115.48 (12)
C8A—C9A—H9AA	109.5	C8B—C9B—H9BA	109.5
C8A—C9A—H9AB	109.5	C8B—C9B—H9BB	109.5
C8A—C9A—H9AC	109.5	C8B—C9B—H9BC	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5
N1A—C2A—C3A—C4A	178.73 (15)	N1B—C2B—C3B—C4B	179.62 (15)
N1A—C2A—C7A—S1A	0.23 (17)	N1B—C2B—C7B—S1B	−1.33 (16)
N1A—C2A—C7A—C6A	−179.33 (14)	N1B—C2B—C7B—C6B	179.88 (14)
C1A—S1A—C7A—C2A	0.29 (11)	C1B—S1B—C7B—C2B	1.31 (11)
C1A—S1A—C7A—C6A	179.81 (15)	C1B—S1B—C7B—C6B	180.00 (15)
C1A—N1A—C2A—C3A	179.14 (15)	C1B—N1B—C2B—C3B	−178.89 (15)
C1A—N1A—C2A—C7A	−0.81 (19)	C1B—N1B—C2B—C7B	0.50 (18)
C1A—N2A—C8A—O1A	−3.1 (2)	C1B—N2B—C8B—O1B	−0.8 (2)
C1A—N2A—C8A—C9A	177.18 (14)	C1B—N2B—C8B—C9B	178.36 (13)
C2A—N1A—C1A—S1A	1.07 (16)	C2B—N1B—C1B—S1B	0.60 (16)
C2A—N1A—C1A—N2A	−179.72 (13)	C2B—N1B—C1B—N2B	−178.39 (13)
C2A—C3A—C4A—C5A	0.9 (3)	C2B—C3B—C4B—C5B	0.4 (3)
C3A—C2A—C7A—S1A	−179.73 (12)	C3B—C2B—C7B—S1B	178.10 (12)
C3A—C2A—C7A—C6A	0.7 (2)	C3B—C2B—C7B—C6B	−0.7 (2)
C3A—C4A—C5A—C6A	0.3 (3)	C3B—C4B—C5B—C6B	−0.7 (3)
C4A—C5A—C6A—C7A	−0.9 (3)	C4B—C5B—C6B—C7B	0.3 (2)
C5A—C6A—C7A—S1A	−179.09 (13)	C5B—C6B—C7B—S1B	−178.14 (13)
C5A—C6A—C7A—C2A	0.4 (2)	C5B—C6B—C7B—C2B	0.4 (2)
C7A—S1A—C1A—N1A	−0.82 (12)	C7B—S1B—C1B—N1B	−1.16 (12)
C7A—S1A—C1A—N2A	179.98 (13)	C7B—S1B—C1B—N2B	177.82 (12)
C7A—C2A—C3A—C4A	−1.3 (2)	C7B—C2B—C3B—C4B	0.2 (2)
C8A—N2A—C1A—S1A	2.6 (2)	C8B—N2B—C1B—S1B	7.6 (2)
C8A—N2A—C1A—N1A	−176.56 (14)	C8B—N2B—C1B—N1B	−173.46 (14)

D—H···A	D—H	H···A	D···A	D—H···A
N2A—H2A···N1B	0.86	2.11	2.9700 (16)	176
N2B—H2B···N1A	0.86	2.14	2.9749 (16)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2A—H2A⋯N1B	0.86	2.11	2.9700 (16)	176
N2B—H2B⋯N1A	0.86	2.14	2.9749 (16)	165