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The mol­ecule of the title compound, C12H11N2FOS, is essentially planar, with a maximum deviation of 0.127 (3) Å for the C atom of the methyl group attached to the thia­zole ring. The structure is stabilized by intra- and inter­molecular hydrogen bonds to form one-dimensional polymeric chains parallel to the b axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030278/ac6203sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030278/ac6203Isup2.hkl
Contains datablock I

CCDC reference: 287434

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.053
  • wR factor = 0.133
  • Data-to-parameter ratio = 13.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.28 PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), is isostructural with 5-acetyl-4-methyl-2-(o-toluidinyl)-1,3-thiazole (Yamin et al., 2005), except that the F atom is bonded at the ortho position of the phenylamino fragment. The whole molecule is essentially planar, with a maximum deviation for atom C12 of 0.127 (3) Å from the least-squares plane; in the molecule of 5-acetyl-4-methyl-2-(o-toluidinyl)-1,3-thiazole, the benzene group is inclined to the thiazole ring by 73.44 (10)°. All bond lengths and angles are in normal ranges (Allen et al., 1987) and are comparable with those in the analogue.

There are weak intramolecular N1—H1···F1, C10—H10B···O1 and C5—H5···N2 hydrogen bonds (Table 2) in the molecule. In the crystal structure, the molecules are linked by intermolecular N1—H1···O1i and C12–H12C···F1ii hydrogen bonds (symmetry codes as in Table 2) to form one-dimensional zigzag polymeric chains parallel to the b axis (Fig. 2).

Experimental top

A solution of o-fluoroaniline (1.11 g, 0.01 mol) in acetone (50 ml) was added dropwise to an acetone solution (50 ml) containing an equimolar amount of 3-chloroacetylacetone and ammonium thiocyanate in a two-necked round-bottomed flask. The solution was refluxed for about 2 h. The light-yellow solution was filtered off and colourless crystals of (I) were obtained after evaporation for 5 d (yield 85%; m.p. 447.8–449.3 K).

Refinement top

All H atoms were located in a difference map. The H atom on N1 was refined isotropically. All other H atoms were fixed geometrically in ideal positions and allowed to ride on their parent C atoms, with C—H distances in the range 0.93–0.96 Å and with Uiso(H) = 1.5Ueq(methyl C), or 1.2Ueq(C) for CH groups.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker or Sheldrick version?); software used to prepare material for publication: SHELXTL (Bruker or Sheldrick version?), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. A packing diagram for (I), viewed down the b axis. Dashed lines denote the N—H···O and C—H···F hydrogen bonds.
5-acetyl-4-methyl-2-(2-fluorophenylamino)-1,3-thiazole top
Crystal data top
C12H11FN2OSF(000) = 520
Mr = 250.29Dx = 1.450 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2840 reflections
a = 5.0205 (11) Åθ = 1.9–26.5°
b = 13.081 (3) ŵ = 0.28 mm1
c = 17.598 (4) ÅT = 273 K
β = 97.085 (4)°Block, colourless
V = 1146.9 (4) Å30.43 × 0.28 × 0.17 mm
Z = 4
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2115 independent reflections
Radiation source: fine-focus sealed tube1931 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 83.66 pixels mm-1θmax = 25.5°, θmin = 1.9°
ω scansh = 65
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
k = 1513
Tmin = 0.889, Tmax = 0.954l = 1321
6015 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.19 w = 1/[σ2(Fo2) + (0.0582P)2 + 0.5434P]
where P = (Fo2 + 2Fc2)/3
2115 reflections(Δ/σ)max < 0.001
160 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C12H11FN2OSV = 1146.9 (4) Å3
Mr = 250.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.0205 (11) ŵ = 0.28 mm1
b = 13.081 (3) ÅT = 273 K
c = 17.598 (4) Å0.43 × 0.28 × 0.17 mm
β = 97.085 (4)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2115 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2000)
1931 reflections with I > 2σ(I)
Tmin = 0.889, Tmax = 0.954Rint = 0.018
6015 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.19Δρmax = 0.23 e Å3
2115 reflectionsΔρmin = 0.19 e Å3
160 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.12589 (13)0.32229 (5)0.26414 (4)0.0482 (2)
F10.7508 (4)0.08384 (12)0.41401 (12)0.0833 (7)
O10.1910 (4)0.58918 (14)0.20516 (12)0.0619 (6)
N10.5354 (4)0.26099 (17)0.36559 (13)0.0484 (6)
N20.4506 (4)0.43875 (16)0.34993 (13)0.0482 (5)
C10.8706 (5)0.16954 (19)0.44555 (16)0.0514 (7)
C21.0930 (6)0.1598 (2)0.49819 (18)0.0609 (8)
H21.16120.09550.51220.073*
C31.2139 (6)0.2462 (2)0.52995 (17)0.0617 (8)
H31.36410.24130.56640.074*
C41.1114 (7)0.3399 (2)0.50755 (19)0.0659 (9)
H41.19380.39860.52900.079*
C50.8872 (6)0.3490 (2)0.45356 (17)0.0592 (8)
H50.82140.41340.43900.071*
C60.7606 (5)0.26238 (19)0.42121 (14)0.0438 (6)
C70.3968 (5)0.34279 (18)0.33349 (15)0.0432 (6)
C80.2696 (5)0.50203 (18)0.30804 (15)0.0457 (6)
C90.0779 (5)0.45396 (18)0.25846 (15)0.0450 (6)
C100.3032 (6)0.6140 (2)0.32002 (19)0.0655 (8)
H10A0.22220.63410.36430.098*
H10B0.21820.64970.27590.098*
H10C0.49090.63050.32760.098*
C110.1413 (5)0.4983 (2)0.20652 (15)0.0463 (6)
C120.3048 (6)0.4262 (2)0.15331 (17)0.0595 (8)
H12A0.42430.38820.18130.089*
H12B0.18730.37970.13140.089*
H12C0.40720.46430.11320.089*
H10.469 (6)0.201 (2)0.3525 (15)0.051 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0497 (4)0.0313 (4)0.0586 (4)0.0017 (2)0.0131 (3)0.0014 (3)
F10.0770 (12)0.0352 (9)0.1239 (16)0.0048 (8)0.0427 (11)0.0047 (9)
O10.0627 (12)0.0372 (11)0.0792 (14)0.0083 (9)0.0179 (10)0.0002 (9)
N10.0513 (13)0.0307 (11)0.0578 (13)0.0010 (9)0.0142 (10)0.0026 (9)
N20.0505 (12)0.0342 (11)0.0558 (13)0.0006 (9)0.0101 (10)0.0007 (9)
C10.0504 (15)0.0355 (13)0.0642 (17)0.0039 (11)0.0087 (13)0.0027 (11)
C20.0588 (17)0.0445 (16)0.0728 (19)0.0029 (12)0.0184 (14)0.0097 (13)
C30.0600 (17)0.0560 (17)0.0623 (18)0.0022 (13)0.0191 (14)0.0013 (14)
C40.0686 (19)0.0481 (17)0.0726 (19)0.0023 (14)0.0255 (15)0.0089 (14)
C50.0678 (18)0.0369 (14)0.0657 (18)0.0032 (12)0.0204 (14)0.0010 (12)
C60.0453 (14)0.0383 (13)0.0458 (14)0.0003 (10)0.0023 (11)0.0028 (10)
C70.0451 (13)0.0344 (12)0.0477 (14)0.0011 (10)0.0040 (11)0.0029 (10)
C80.0474 (14)0.0333 (13)0.0538 (15)0.0006 (10)0.0049 (11)0.0002 (10)
C90.0448 (13)0.0337 (13)0.0541 (15)0.0007 (10)0.0036 (11)0.0014 (10)
C100.0717 (19)0.0354 (14)0.081 (2)0.0028 (13)0.0234 (16)0.0052 (13)
C110.0439 (14)0.0392 (14)0.0538 (15)0.0021 (10)0.0027 (11)0.0024 (11)
C120.0564 (16)0.0480 (15)0.0678 (18)0.0040 (13)0.0169 (14)0.0043 (13)
Geometric parameters (Å, º) top
S1—C71.733 (3)C4—C51.385 (4)
S1—C91.740 (2)C4—H40.9300
F1—C11.358 (3)C5—C61.386 (4)
O1—C111.214 (3)C5—H50.9300
N1—C71.360 (3)C8—C91.370 (4)
N1—C61.401 (3)C8—C101.486 (4)
N1—H10.87 (3)C9—C111.461 (3)
N2—C71.309 (3)C10—H10A0.9600
N2—C81.375 (3)C10—H10B0.9600
C1—C21.366 (4)C10—H10C0.9600
C1—C61.380 (3)C11—C121.501 (4)
C2—C31.369 (4)C12—H12A0.9600
C2—H20.9300C12—H12B0.9600
C3—C41.368 (4)C12—H12C0.9600
C3—H30.9300
C7—S1—C988.76 (11)N2—C7—S1115.27 (18)
C7—N1—C6127.4 (2)N1—C7—S1119.17 (18)
C7—N1—H1116.2 (18)C9—C8—N2115.6 (2)
C6—N1—H1116.3 (18)C9—C8—C10127.0 (2)
C7—N2—C8110.8 (2)N2—C8—C10117.5 (2)
F1—C1—C2119.0 (2)C8—C9—C11129.2 (2)
F1—C1—C6117.3 (2)C8—C9—S1109.66 (18)
C2—C1—C6123.7 (2)C11—C9—S1121.15 (19)
C1—C2—C3118.9 (3)C8—C10—H10A109.5
C1—C2—H2120.5C8—C10—H10B109.5
C3—C2—H2120.5H10A—C10—H10B109.5
C4—C3—C2119.3 (3)C8—C10—H10C109.5
C4—C3—H3120.3H10A—C10—H10C109.5
C2—C3—H3120.3H10B—C10—H10C109.5
C3—C4—C5121.3 (3)O1—C11—C9122.6 (2)
C3—C4—H4119.4O1—C11—C12120.6 (2)
C5—C4—H4119.4C9—C11—C12116.9 (2)
C4—C5—C6120.3 (3)C11—C12—H12A109.5
C4—C5—H5119.9C11—C12—H12B109.5
C6—C5—H5119.9H12A—C12—H12B109.5
C1—C6—C5116.5 (2)C11—C12—H12C109.5
C1—C6—N1117.6 (2)H12A—C12—H12C109.5
C5—C6—N1126.0 (2)H12B—C12—H12C109.5
N2—C7—N1125.6 (2)
F1—C1—C2—C3180.0 (3)C6—N1—C7—S1179.0 (2)
C6—C1—C2—C30.9 (5)C9—S1—C7—N21.2 (2)
C1—C2—C3—C40.8 (5)C9—S1—C7—N1179.2 (2)
C2—C3—C4—C50.2 (5)C7—N2—C8—C90.8 (3)
C3—C4—C5—C60.3 (5)C7—N2—C8—C10179.9 (3)
F1—C1—C6—C5179.4 (3)N2—C8—C9—C11179.8 (3)
C2—C1—C6—C50.4 (5)C10—C8—C9—C111.1 (5)
F1—C1—C6—N10.4 (4)N2—C8—C9—S10.1 (3)
C2—C1—C6—N1178.6 (3)C10—C8—C9—S1178.9 (3)
C4—C5—C6—C10.2 (5)C7—S1—C9—C80.7 (2)
C4—C5—C6—N1179.2 (3)C7—S1—C9—C11179.2 (2)
C7—N1—C6—C1179.7 (3)C8—C9—C11—O15.2 (5)
C7—N1—C6—C50.8 (5)S1—C9—C11—O1174.8 (2)
C8—N2—C7—N1179.1 (3)C8—C9—C11—C12174.3 (3)
C8—N2—C7—S11.4 (3)S1—C9—C11—C125.8 (3)
C6—N1—C7—N20.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F10.87 (3)2.27 (3)2.653 (3)107 (2)
C5—H5···N20.932.302.919 (4)123
C10—H10B···O10.962.403.018 (4)122
N1—H1···O1i0.87 (3)2.18 (3)3.010 (3)158 (3)
C12—H12C···F1ii0.962.333.165 (3)144
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC12H11FN2OS
Mr250.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)273
a, b, c (Å)5.0205 (11), 13.081 (3), 17.598 (4)
β (°) 97.085 (4)
V3)1146.9 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.28
Crystal size (mm)0.43 × 0.28 × 0.17
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2000)
Tmin, Tmax0.889, 0.954
No. of measured, independent and
observed [I > 2σ(I)] reflections
6015, 2115, 1931
Rint0.018
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.133, 1.19
No. of reflections2115
No. of parameters160
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.19

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXTL (Bruker, 2000), SHELXTL (Sheldrick, 1997), SHELXTL (Bruker or Sheldrick version?), PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top
S1—C71.733 (3)N1—C61.401 (3)
S1—C91.740 (2)N2—C71.309 (3)
F1—C11.358 (3)N2—C81.375 (3)
O1—C111.214 (3)C8—C91.370 (4)
N1—C71.360 (3)
C7—S1—C988.76 (11)C7—N2—C8110.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···F10.87 (3)2.27 (3)2.653 (3)107 (2)
C5—H5···N20.932.302.919 (4)123
C10—H10B···O10.962.403.018 (4)122
N1—H1···O1i0.87 (3)2.18 (3)3.010 (3)158 (3)
C12—H12C···F1ii0.962.333.165 (3)144
Symmetry codes: (i) x, y1/2, z+1/2; (ii) x, y+1/2, z+1/2.
 

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