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

In the title compound, C(11)H(9)FN(2)OS, the 1,3-thia-zole ring is planar (r.m.s. deviation = 0.007 Å) and forms a dihedral angle of 73.75 (5)° with the benzene ring. In the crystal, mol-ecules are linked via pairs of N-H⋯N and C-H⋯F hydrogen bonds into chains along [100].

Related literature

For general background to the title compound and for related structures, see: Fun et al. (2011a ▶,b ▶, 2012a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H9FN2OS

M = 236.26

Monoclinic,

a = 11.9043 (13) Å

b = 5.2969 (6) Å

c = 16.4579 (18) Å

β = 90.397 (3)°

V = 1037.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 100 K

0.26 × 0.18 × 0.12 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.924, T max = 0.965

12231 measured reflections

3722 independent reflections

3092 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.05

3722 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.47 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812032989/rz2790sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032989/rz2790Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032989/rz2790Isup3.cml

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

C11H9FN2OS	F(000) = 488
Mr = 236.26	Dx = 1.512 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4325 reflections
a = 11.9043 (13) Å	θ = 4.0–32.5°
b = 5.2969 (6) Å	µ = 0.30 mm−1
c = 16.4579 (18) Å	T = 100 K
β = 90.397 (3)°	Block, colourless
V = 1037.7 (2) Å3	0.26 × 0.18 × 0.12 mm
Z = 4

Bruker SMART APEXII DUO CCD area-detector diffractometer	3722 independent reflections
Radiation source: fine-focus sealed tube	3092 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 32.6°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→18
Tmin = 0.924, Tmax = 0.965	k = −8→7
12231 measured reflections	l = −24→24

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.3919P] where P = (Fo2 + 2Fc2)/3
3722 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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 > 2sigma(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
F1	0.11704 (6)	0.19317 (14)	0.03863 (4)	0.02223 (16)
S1	0.48132 (2)	0.00859 (5)	0.172709 (16)	0.01629 (7)
O1	0.28432 (7)	0.26500 (17)	0.18303 (5)	0.01993 (17)
N1	0.57205 (8)	0.22624 (18)	0.04881 (6)	0.01618 (17)
N2	0.39938 (7)	0.40844 (19)	0.08374 (6)	0.01519 (17)
C1	0.60857 (9)	−0.1033 (2)	0.13824 (7)	0.0184 (2)
H1A	0.6491	−0.2397	0.1618	0.022*
C2	0.64234 (9)	0.0308 (2)	0.07290 (7)	0.0176 (2)
H2A	0.7101	−0.0065	0.0452	0.021*
C3	0.48369 (8)	0.2335 (2)	0.09615 (6)	0.01391 (18)
C4	0.30210 (9)	0.4142 (2)	0.12773 (6)	0.01507 (19)
C5	0.22188 (9)	0.6224 (2)	0.10236 (7)	0.0186 (2)
H5A	0.2419	0.7787	0.1321	0.022*
H5B	0.2314	0.6559	0.0436	0.022*
C6	0.10050 (8)	0.5610 (2)	0.11813 (6)	0.01376 (18)
C7	0.03141 (9)	0.7177 (2)	0.16408 (6)	0.01611 (19)
H7A	0.0621	0.8652	0.1884	0.019*
C8	−0.08201 (9)	0.6617 (2)	0.17497 (7)	0.0185 (2)
H8A	−0.1279	0.7711	0.2062	0.022*
C9	−0.12777 (9)	0.4461 (2)	0.14008 (7)	0.0199 (2)
H9A	−0.2049	0.4076	0.1478	0.024*
C10	−0.06080 (9)	0.2858 (2)	0.09371 (7)	0.0181 (2)
H10A	−0.0912	0.1380	0.0693	0.022*
C11	0.05083 (9)	0.3483 (2)	0.08436 (6)	0.01515 (19)
H1N2	0.4086 (14)	0.506 (3)	0.0437 (10)	0.027 (4)*

	U11	U22	U33	U12	U13	U23
F1	0.0244 (3)	0.0189 (3)	0.0235 (3)	0.0046 (3)	0.0039 (3)	−0.0076 (3)
S1	0.01630 (12)	0.01661 (13)	0.01597 (12)	0.00145 (10)	0.00162 (8)	0.00255 (9)
O1	0.0171 (3)	0.0237 (4)	0.0191 (3)	0.0032 (3)	0.0045 (3)	0.0065 (3)
N1	0.0135 (4)	0.0153 (4)	0.0198 (4)	0.0008 (3)	0.0028 (3)	0.0007 (3)
N2	0.0135 (4)	0.0149 (4)	0.0172 (4)	0.0017 (3)	0.0033 (3)	0.0031 (3)
C1	0.0156 (4)	0.0175 (5)	0.0220 (5)	0.0029 (4)	−0.0010 (4)	0.0016 (4)
C2	0.0135 (4)	0.0173 (5)	0.0222 (5)	0.0010 (4)	0.0010 (4)	−0.0003 (4)
C3	0.0134 (4)	0.0128 (4)	0.0155 (4)	−0.0010 (4)	0.0007 (3)	−0.0006 (3)
C4	0.0129 (4)	0.0163 (5)	0.0160 (4)	−0.0006 (4)	0.0015 (3)	−0.0002 (4)
C5	0.0141 (4)	0.0164 (5)	0.0254 (5)	0.0010 (4)	0.0032 (4)	0.0036 (4)
C6	0.0130 (4)	0.0138 (4)	0.0145 (4)	0.0007 (4)	0.0010 (3)	0.0011 (3)
C7	0.0176 (4)	0.0145 (5)	0.0163 (4)	0.0015 (4)	0.0010 (3)	−0.0016 (4)
C8	0.0177 (5)	0.0195 (5)	0.0186 (5)	0.0054 (4)	0.0042 (4)	0.0010 (4)
C9	0.0136 (4)	0.0216 (5)	0.0244 (5)	0.0008 (4)	0.0015 (4)	0.0046 (4)
C10	0.0168 (4)	0.0156 (5)	0.0219 (5)	−0.0012 (4)	−0.0032 (4)	0.0008 (4)
C11	0.0169 (4)	0.0139 (5)	0.0147 (4)	0.0030 (4)	0.0015 (3)	−0.0017 (4)

F1—C11	1.3679 (12)	C5—C6	1.5054 (15)
S1—C1	1.7262 (11)	C5—H5A	0.9900
S1—C3	1.7344 (11)	C5—H5B	0.9900
O1—C4	1.2248 (13)	C6—C11	1.3866 (15)
N1—C3	1.3139 (13)	C6—C7	1.3951 (14)
N1—C2	1.3872 (15)	C7—C8	1.3952 (15)
N2—C4	1.3704 (13)	C7—H7A	0.9500
N2—C3	1.3802 (14)	C8—C9	1.3878 (17)
N2—H1N2	0.846 (17)	C8—H8A	0.9500
C1—C2	1.3524 (16)	C9—C10	1.3956 (16)
C1—H1A	0.9500	C9—H9A	0.9500
C2—H2A	0.9500	C10—C11	1.3791 (15)
C4—C5	1.5156 (16)	C10—H10A	0.9500
C1—S1—C3	88.76 (5)	C4—C5—H5B	108.9
C3—N1—C2	109.65 (9)	H5A—C5—H5B	107.7
C4—N2—C3	123.58 (9)	C11—C6—C7	116.69 (10)
C4—N2—H1N2	120.8 (12)	C11—C6—C5	120.92 (9)
C3—N2—H1N2	115.4 (12)	C7—C6—C5	122.34 (10)
C2—C1—S1	110.32 (9)	C6—C7—C8	121.19 (10)
C2—C1—H1A	124.8	C6—C7—H7A	119.4
S1—C1—H1A	124.8	C8—C7—H7A	119.4
C1—C2—N1	115.93 (10)	C9—C8—C7	119.94 (10)
C1—C2—H2A	122.0	C9—C8—H8A	120.0
N1—C2—H2A	122.0	C7—C8—H8A	120.0
N1—C3—N2	121.08 (10)	C8—C9—C10	120.20 (10)
N1—C3—S1	115.33 (8)	C8—C9—H9A	119.9
N2—C3—S1	123.59 (8)	C10—C9—H9A	119.9
O1—C4—N2	121.95 (10)	C11—C10—C9	117.99 (11)
O1—C4—C5	124.23 (9)	C11—C10—H10A	121.0
N2—C4—C5	113.82 (9)	C9—C10—H10A	121.0
C6—C5—C4	113.50 (9)	F1—C11—C10	118.45 (10)
C6—C5—H5A	108.9	F1—C11—C6	117.56 (9)
C4—C5—H5A	108.9	C10—C11—C6	123.98 (10)
C6—C5—H5B	108.9
C3—S1—C1—C2	−0.63 (9)	C4—C5—C6—C11	−57.78 (14)
S1—C1—C2—N1	1.22 (13)	C4—C5—C6—C7	124.88 (11)
C3—N1—C2—C1	−1.27 (14)	C11—C6—C7—C8	−0.15 (15)
C2—N1—C3—N2	−178.59 (10)	C5—C6—C7—C8	177.30 (10)
C2—N1—C3—S1	0.73 (12)	C6—C7—C8—C9	0.31 (17)
C4—N2—C3—N1	175.57 (10)	C7—C8—C9—C10	−0.36 (17)
C4—N2—C3—S1	−3.70 (15)	C8—C9—C10—C11	0.25 (17)
C1—S1—C3—N1	−0.07 (9)	C9—C10—C11—F1	−179.62 (10)
C1—S1—C3—N2	179.23 (10)	C9—C10—C11—C6	−0.09 (17)
C3—N2—C4—O1	1.54 (17)	C7—C6—C11—F1	179.57 (9)
C3—N2—C4—C5	−179.49 (10)	C5—C6—C11—F1	2.08 (15)
O1—C4—C5—C6	−29.04 (16)	C7—C6—C11—C10	0.04 (16)
N2—C4—C5—C6	152.01 (10)	C5—C6—C11—C10	−177.45 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···N1i	0.845 (16)	2.095 (16)	2.9376 (14)	175.0 (16)
C10—H10A···F1ii	0.95	2.51	3.4071 (14)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1i	0.845 (16)	2.095 (16)	2.9376 (14)	175.0 (16)
C10—H10A⋯F1ii	0.95	2.51	3.4071 (14)	157

Symmetry codes: (i) ; (ii) .