2-(2-Fluoro­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide

Fun, H.-K.; Quah, C.K.; Nayak, P.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812032989

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2565

https://doi.org/10.1107/S1600536812032989

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2-(2-Fluorophenyl)-N-(1,3-thiazol-2-yl)acetamide

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § Prakash S. Nayak,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 10 July 2012; accepted 20 July 2012; online 28 July 2012)

In the title compound, C₁₁H₉FN₂OS, the 1,3-thiazole 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, molecules 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_r = 236.26
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.090
S = 1.05
3722 reflections
149 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x+1, -y+1, -z; (ii) -x, -y, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812032989/rz2790sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812032989/rz2790Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812032989/rz2790Isup3.cml

checkCIF report

Comment top

In continuation of our work on synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the thiazol-2-yl ring (S1/N1/C1-C3) is nearly planar (r.m.s. deviation = 0.007 Å) and forms a dihedral angle of 73.75 (5)° with the benzene ring (C6-C11). Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those reported for related structures (Fun et al., 2011a, 2011b, 2012a, 2012b). In the crystal structure (Fig. 2), molecules are linked via pairs of intermolecular N2–H1N2···N1 and C10–H10A···F1 hydrogen bonds (Table 1) into one-dimensional chains along [100].

Related literature top

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 top

2-Fluorolphenylacetic acid (0.154 g, 1 mmol), 2-aminothiazole (0.1 g, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (1.0 g, 0.01 mol) were dissolved in dichloromethane (20 mL). The mixture was stirred in presence of triethylamine at 273 K for about 3 h. The contents were poured into 100 mL of ice-cold aqueous hydrochloric acid with stirring and was then extracted thrice with dichloromethane. The organic layer was washed with saturated NaHCO₃ solution and brine solution, dried and concentrated under reduced pressure to give the title compound. Single crystals were grown from acetone and toluene (1:1 v/v) mixture by the slow evaporation method (m.p.: 453-455 K).

Structure description top

In continuation of our work on synthesis of amides (Fun et al., 2011a, 2011b, 2012a, 2012b), we report herein the crystal structure of the title compound.

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The crystal structure of the title compound, viewed along the b axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

2-(2-Fluorophenyl)-N-(1,3-thiazol-2-yl)acetamide top

Crystal data top

C₁₁H₉FN₂OS	F(000) = 488
M_r = 236.26	D_x = 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

Data collection top

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	R_int = 0.030
φ and ω scans	θ_max = 32.6°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→18
T_min = 0.924, T_max = 0.965	k = −8→7
12231 measured reflections	l = −24→24

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)] = 0.034	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(F_o²) + (0.0396P)² + 0.3919P] where P = (F_o² + 2F_c²)/3
3722 reflections	(Δ/σ)_max = 0.001
149 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₁H₉FN₂OS	V = 1037.7 (2) Å³
M_r = 236.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9043 (13) Å	µ = 0.30 mm⁻¹
b = 5.2969 (6) Å	T = 100 K
c = 16.4579 (18) Å	0.26 × 0.18 × 0.12 mm
β = 90.397 (3)°

Data collection top

Bruker SMART APEXII DUO CCD area-detector diffractometer	3722 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3092 reflections with I > 2σ(I)
T_min = 0.924, T_max = 0.965	R_int = 0.030
12231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.47 e Å⁻³
3722 reflections	Δρ_min = −0.26 e Å⁻³
149 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z; (ii) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₁H₉FN₂OS
M_r	236.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	11.9043 (13), 5.2969 (6), 16.4579 (18)
β (°)	90.397 (3)
V (Å³)	1037.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.26 × 0.18 × 0.12

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.924, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	12231, 3722, 3092
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.090, 1.05
No. of reflections	3722
No. of parameters	149
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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	0.9500	2.5100	3.4071 (14)	157.00

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for the Research University Grant (No. 1001/PFIZIK/811160). BN also thanks the UGC, New Delhi, and the Government of India for the purchase of chemicals through the SAP–DRS-Phase 1 programme.

References

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