organic compounds
2-Fluoroanilinium N-(2-fluorophenyl)oxamate
aDepartment of Physics, Faculty of Arts & Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, and bDepartment of Chemistry, Faculty of Arts & Sciences, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey
*Correspondence e-mail: orhanb@omu.edu.tr
The 6H7FN+·C8H5FNO3−, exhibits intramolecular N—H⋯O and C—H⋯O and intermolecular N—H⋯O and N—H⋯F hydrogen-bond interactions, the intramolecular hydrogen-bond interactions generating S(6) and S(5) ring motifs. The dihedral angles between the aromatic ring and the intramolecular hydrogen-bonded rings in the anion are 2.97 (7) and 6.70 (5)°. The two aromatic rings of the title compound are oriented with a dihedral angle of 77.25 (9)°.
of the title salt, CRelated literature
For related structures see: Odabaşoğlu & Büyükgüngör (2006a,b,c); Büyükgüngör & Odabaşoğlu (2007). For ring motif details, see: Bernstein et al. (1995); Etter (1990).
Experimental
Crystal data
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Supporting information
10.1107/S1600536808008891/at2556sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008891/at2556Isup2.hkl
The title compound was prepared according to the method described by Büyükgüngör & Odabaşoǧlu (2006b), using 2-fluoroaniline and oxalic acid as starting materials (yield 90%). Crystals of (I) suitable for x-ray analysis were obtained by slow evaporation of an ethanol (95%) solution at room temperature.
H atom (for NH3) was located in difference synthesis and refined freely. The remaining H atoms were positioned geometrically, with C—H = 0.93 for aromatic H and N—H = 0.86 Å for amine H, and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(parent).
Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The hydrogen bonds are drawn as dashed lines. | |
Fig. 2. A partial packing diagram of (I), showing the formation of R12(5)R42(8)R44(12) motifs. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry codes: (i) 1 - x, 1 - y, z; (ii) x, y - 1, z; (iii) -x, y, -z; (iv) 1 - x, -y, -z; (v) -x, -y, -z]. | |
Fig. 3. A partial packing diagram of (I), showing the formation of R22(10) motif. H atoms not involved in hydrogen bonds have been omitted for clarity. [Symmetry code: (i) 1 - x, -y, 1 - z]. |
C6H7FN+·C8H5FNO3− | Z = 2 |
Mr = 294.26 | F(000) = 304 |
Triclinic, P1 | Dx = 1.429 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7118 (9) Å | Cell parameters from 9218 reflections |
b = 9.5998 (14) Å | θ = 1.9–28.1° |
c = 11.7000 (16) Å | µ = 0.12 mm−1 |
α = 68.346 (11)° | T = 296 K |
β = 85.791 (11)° | Plate, colourless |
γ = 77.375 (11)° | 0.78 × 0.47 × 0.09 mm |
V = 683.69 (18) Å3 |
Stoe IPDSII diffractometer | 2684 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 2023 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.040 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.9° |
ω rotation method scans | h = −8→8 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −11→11 |
Tmin = 0.932, Tmax = 0.988 | l = −14→14 |
9218 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.168 | w = 1/[σ2(Fo2) + (0.1051P)2 + 0.5375P] where P = (Fo2 + 2Fc2)/3 |
S = 0.81 | (Δ/σ)max < 0.001 |
2684 reflections | Δρmax = 0.53 e Å−3 |
203 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.026 (7) |
C6H7FN+·C8H5FNO3− | γ = 77.375 (11)° |
Mr = 294.26 | V = 683.69 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.7118 (9) Å | Mo Kα radiation |
b = 9.5998 (14) Å | µ = 0.12 mm−1 |
c = 11.7000 (16) Å | T = 296 K |
α = 68.346 (11)° | 0.78 × 0.47 × 0.09 mm |
β = 85.791 (11)° |
Stoe IPDSII diffractometer | 2684 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 2023 reflections with I > 2σ(I) |
Tmin = 0.932, Tmax = 0.988 | Rint = 0.040 |
9218 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 0 restraints |
wR(F2) = 0.168 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.53 e Å−3 |
2684 reflections | Δρmin = −0.30 e Å−3 |
203 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0927 (4) | 0.1895 (3) | 0.4566 (2) | 0.0500 (6) | |
C2 | 0.2329 (5) | 0.2000 (4) | 0.5327 (3) | 0.0662 (7) | |
C3 | 0.1793 (7) | 0.2559 (5) | 0.6239 (3) | 0.0882 (10) | |
H3 | 0.2783 | 0.2599 | 0.6735 | 0.106* | |
C4 | −0.0226 (7) | 0.3060 (5) | 0.6414 (3) | 0.0958 (12) | |
H4 | −0.0625 | 0.3456 | 0.7030 | 0.115* | |
C5 | −0.1675 (6) | 0.2980 (4) | 0.5682 (3) | 0.0826 (9) | |
H5 | −0.3050 | 0.3322 | 0.5809 | 0.099* | |
C6 | −0.1122 (4) | 0.2399 (3) | 0.4759 (2) | 0.0619 (7) | |
H6 | −0.2116 | 0.2347 | 0.4272 | 0.074* | |
C7 | 0.0672 (3) | 0.1176 (3) | 0.2757 (2) | 0.0452 (5) | |
C8 | 0.2108 (3) | 0.0541 (3) | 0.1899 (2) | 0.0472 (5) | |
C9 | 0.5179 (4) | 0.6758 (3) | 0.1045 (2) | 0.0592 (7) | |
C10 | 0.3396 (3) | 0.7306 (3) | 0.0369 (2) | 0.0447 (5) | |
C11 | 0.2088 (5) | 0.6328 (3) | 0.0524 (3) | 0.0625 (7) | |
H11 | 0.0855 | 0.6678 | 0.0095 | 0.075* | |
C12 | 0.2612 (6) | 0.4827 (4) | 0.1318 (3) | 0.0804 (9) | |
H12 | 0.1723 | 0.4171 | 0.1420 | 0.097* | |
C13 | 0.4415 (6) | 0.4291 (4) | 0.1955 (3) | 0.0803 (9) | |
H13 | 0.4763 | 0.3270 | 0.2472 | 0.096* | |
C14 | 0.5722 (5) | 0.5263 (4) | 0.1834 (3) | 0.0787 (9) | |
H14 | 0.6942 | 0.4915 | 0.2277 | 0.094* | |
N1 | 0.1682 (3) | 0.1288 (2) | 0.36637 (17) | 0.0496 (5) | |
H1 | 0.2978 | 0.0935 | 0.3692 | 0.060* | |
N2 | 0.2905 (3) | 0.8889 (2) | −0.04487 (19) | 0.0447 (5) | |
O1 | −0.1162 (3) | 0.1563 (2) | 0.25841 (17) | 0.0638 (5) | |
O2 | 0.1240 (3) | 0.0321 (2) | 0.10956 (16) | 0.0587 (5) | |
O3 | 0.3972 (3) | 0.0349 (2) | 0.20670 (16) | 0.0651 (5) | |
F1 | 0.4339 (3) | 0.1515 (3) | 0.51255 (18) | 0.0919 (7) | |
F2 | 0.6443 (3) | 0.7710 (2) | 0.0900 (2) | 0.1002 (7) | |
H2A | 0.243 (5) | 0.946 (3) | 0.004 (3) | 0.069 (8)* | |
H2B | 0.396 (5) | 0.915 (3) | −0.094 (3) | 0.064 (8)* | |
H2C | 0.187 (5) | 0.898 (3) | −0.092 (3) | 0.073 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0559 (14) | 0.0517 (13) | 0.0407 (12) | −0.0165 (11) | 0.0003 (10) | −0.0118 (10) |
C2 | 0.0678 (18) | 0.0816 (19) | 0.0546 (15) | −0.0240 (15) | −0.0014 (13) | −0.0257 (14) |
C3 | 0.107 (3) | 0.115 (3) | 0.0628 (19) | −0.040 (2) | 0.0018 (18) | −0.0461 (19) |
C4 | 0.134 (4) | 0.105 (3) | 0.068 (2) | −0.035 (2) | 0.020 (2) | −0.051 (2) |
C5 | 0.086 (2) | 0.090 (2) | 0.075 (2) | −0.0135 (18) | 0.0180 (17) | −0.0395 (18) |
C6 | 0.0621 (16) | 0.0686 (17) | 0.0554 (15) | −0.0137 (13) | 0.0054 (12) | −0.0239 (13) |
C7 | 0.0433 (13) | 0.0461 (12) | 0.0438 (12) | −0.0093 (10) | −0.0035 (9) | −0.0128 (10) |
C8 | 0.0418 (12) | 0.0501 (13) | 0.0448 (12) | −0.0068 (10) | −0.0029 (9) | −0.0124 (10) |
C9 | 0.0528 (15) | 0.0617 (16) | 0.0590 (15) | −0.0124 (12) | −0.0016 (12) | −0.0166 (12) |
C10 | 0.0465 (12) | 0.0475 (12) | 0.0420 (11) | −0.0057 (10) | 0.0015 (9) | −0.0211 (10) |
C11 | 0.0719 (18) | 0.0591 (16) | 0.0633 (16) | −0.0226 (13) | −0.0022 (13) | −0.0243 (13) |
C12 | 0.102 (3) | 0.0582 (18) | 0.083 (2) | −0.0320 (17) | 0.0009 (19) | −0.0194 (16) |
C13 | 0.102 (3) | 0.0503 (16) | 0.0728 (19) | −0.0055 (16) | 0.0036 (18) | −0.0103 (14) |
C14 | 0.0662 (19) | 0.078 (2) | 0.0695 (19) | 0.0046 (16) | −0.0092 (15) | −0.0104 (16) |
N1 | 0.0409 (10) | 0.0623 (12) | 0.0463 (11) | −0.0105 (9) | −0.0033 (8) | −0.0198 (9) |
N2 | 0.0391 (11) | 0.0510 (11) | 0.0458 (11) | −0.0096 (8) | −0.0009 (9) | −0.0192 (9) |
O1 | 0.0404 (10) | 0.0909 (14) | 0.0671 (11) | −0.0012 (9) | −0.0080 (8) | −0.0420 (10) |
O2 | 0.0498 (10) | 0.0734 (12) | 0.0605 (10) | −0.0046 (8) | −0.0034 (8) | −0.0369 (9) |
O3 | 0.0402 (10) | 0.0987 (15) | 0.0522 (10) | −0.0088 (9) | −0.0004 (7) | −0.0254 (10) |
F1 | 0.0653 (11) | 0.1443 (18) | 0.0815 (12) | −0.0250 (11) | −0.0134 (9) | −0.0540 (12) |
F2 | 0.0742 (12) | 0.0985 (15) | 0.1081 (15) | −0.0317 (10) | −0.0328 (11) | −0.0010 (12) |
C1—C6 | 1.386 (4) | C9—F2 | 1.337 (3) |
C1—C2 | 1.385 (4) | C9—C14 | 1.374 (4) |
C1—N1 | 1.399 (3) | C9—C10 | 1.375 (3) |
C2—C3 | 1.356 (5) | C10—C11 | 1.377 (3) |
C2—F1 | 1.361 (4) | C10—N2 | 1.445 (3) |
C3—C4 | 1.363 (5) | C11—C12 | 1.378 (4) |
C3—H3 | 0.9300 | C11—H11 | 0.9300 |
C4—C5 | 1.375 (5) | C12—C13 | 1.365 (5) |
C4—H4 | 0.9300 | C12—H12 | 0.9300 |
C5—C6 | 1.381 (4) | C13—C14 | 1.379 (5) |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—H6 | 0.9300 | C14—H14 | 0.9300 |
C7—O1 | 1.214 (3) | N1—H1 | 0.8600 |
C7—N1 | 1.349 (3) | N2—H2A | 0.93 (3) |
C7—C8 | 1.536 (3) | N2—H2B | 0.90 (3) |
C8—O3 | 1.244 (3) | N2—H2C | 0.89 (3) |
C8—O2 | 1.244 (3) | ||
C6—C1—C2 | 117.3 (2) | C14—C9—C10 | 122.3 (3) |
C6—C1—N1 | 125.0 (2) | C9—C10—C11 | 118.4 (2) |
C2—C1—N1 | 117.7 (2) | C9—C10—N2 | 119.9 (2) |
C3—C2—F1 | 119.5 (3) | C11—C10—N2 | 121.7 (2) |
C3—C2—C1 | 123.4 (3) | C12—C11—C10 | 119.8 (3) |
F1—C2—C1 | 117.0 (2) | C12—C11—H11 | 120.1 |
C2—C3—C4 | 118.7 (3) | C10—C11—H11 | 120.1 |
C2—C3—H3 | 120.7 | C13—C12—C11 | 120.9 (3) |
C4—C3—H3 | 120.7 | C13—C12—H12 | 119.5 |
C3—C4—C5 | 120.0 (3) | C11—C12—H12 | 119.5 |
C3—C4—H4 | 120.0 | C12—C13—C14 | 120.1 (3) |
C5—C4—H4 | 120.0 | C12—C13—H13 | 120.0 |
C6—C5—C4 | 121.1 (3) | C14—C13—H13 | 120.0 |
C6—C5—H5 | 119.5 | C9—C14—C13 | 118.5 (3) |
C4—C5—H5 | 119.5 | C9—C14—H14 | 120.8 |
C5—C6—C1 | 119.5 (3) | C13—C14—H14 | 120.8 |
C5—C6—H6 | 120.3 | C7—N1—C1 | 129.4 (2) |
C1—C6—H6 | 120.3 | C7—N1—H1 | 115.3 |
O1—C7—N1 | 125.5 (2) | C1—N1—H1 | 115.3 |
O1—C7—C8 | 121.8 (2) | C10—N2—H2A | 106.5 (18) |
N1—C7—C8 | 112.65 (19) | C10—N2—H2B | 111.4 (18) |
O3—C8—O2 | 128.1 (2) | H2A—N2—H2B | 116 (3) |
O3—C8—C7 | 116.8 (2) | C10—N2—H2C | 106.7 (19) |
O2—C8—C7 | 115.1 (2) | H2A—N2—H2C | 108 (3) |
F2—C9—C14 | 119.3 (3) | H2B—N2—H2C | 108 (3) |
F2—C9—C10 | 118.4 (2) | ||
C6—C1—C2—C3 | 0.2 (4) | F2—C9—C10—C11 | −179.6 (2) |
N1—C1—C2—C3 | −179.6 (3) | C14—C9—C10—C11 | 2.2 (4) |
C6—C1—C2—F1 | −179.5 (2) | F2—C9—C10—N2 | −1.7 (4) |
N1—C1—C2—F1 | 0.7 (4) | C14—C9—C10—N2 | −179.9 (3) |
F1—C2—C3—C4 | 179.0 (3) | C9—C10—C11—C12 | −1.8 (4) |
C1—C2—C3—C4 | −0.7 (5) | N2—C10—C11—C12 | −179.7 (3) |
C2—C3—C4—C5 | 0.6 (6) | C10—C11—C12—C13 | 0.0 (5) |
C3—C4—C5—C6 | −0.2 (6) | C11—C12—C13—C14 | 1.6 (5) |
C4—C5—C6—C1 | −0.3 (5) | F2—C9—C14—C13 | −178.8 (3) |
C2—C1—C6—C5 | 0.2 (4) | C10—C9—C14—C13 | −0.6 (5) |
N1—C1—C6—C5 | −179.9 (3) | C12—C13—C14—C9 | −1.3 (5) |
O1—C7—C8—O3 | 171.7 (2) | O1—C7—N1—C1 | −2.4 (4) |
N1—C7—C8—O3 | −6.3 (3) | C8—C7—N1—C1 | 175.6 (2) |
O1—C7—C8—O2 | −6.5 (3) | C6—C1—N1—C7 | 6.0 (4) |
N1—C7—C8—O2 | 175.5 (2) | C2—C1—N1—C7 | −174.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 2.19 | 2.623 (3) | 111 |
N1—H1···F1i | 0.86 | 2.61 | 3.313 (3) | 140 |
N2—H2A···O2ii | 0.93 (3) | 1.77 (3) | 2.696 (3) | 170 (3) |
N2—H2B···O3iii | 0.90 (3) | 1.86 (3) | 2.753 (3) | 174 (3) |
N2—H2C···O2iv | 0.89 (3) | 2.05 (3) | 2.802 (3) | 142 (3) |
N2—H2C···O1iv | 0.89 (3) | 2.30 (3) | 3.041 (3) | 141 (3) |
C6—H6···O1 | 0.93 | 2.36 | 2.941 (3) | 120 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C6H7FN+·C8H5FNO3− |
Mr | 294.26 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 6.7118 (9), 9.5998 (14), 11.7000 (16) |
α, β, γ (°) | 68.346 (11), 85.791 (11), 77.375 (11) |
V (Å3) | 683.69 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.78 × 0.47 × 0.09 |
Data collection | |
Diffractometer | Stoe IPDSII diffractometer |
Absorption correction | Integration (X-RED32; Stoe & Cie, 2002) |
Tmin, Tmax | 0.932, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9218, 2684, 2023 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.168, 0.81 |
No. of reflections | 2684 |
No. of parameters | 203 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.53, −0.30 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.86 | 2.19 | 2.623 (3) | 110.6 |
N1—H1···F1i | 0.86 | 2.61 | 3.313 (3) | 140.0 |
N2—H2A···O2ii | 0.93 (3) | 1.77 (3) | 2.696 (3) | 170 (3) |
N2—H2B···O3iii | 0.90 (3) | 1.86 (3) | 2.753 (3) | 174 (3) |
N2—H2C···O2iv | 0.89 (3) | 2.05 (3) | 2.802 (3) | 142 (3) |
N2—H2C···O1iv | 0.89 (3) | 2.30 (3) | 3.041 (3) | 141 (3) |
C6—H6···O1 | 0.93 | 2.36 | 2.941 (3) | 120.2 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x, −y+1, −z. |
Acknowledgements
The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F. 279 of the University Research Fund).
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The present work is part of a structural study of compounds of anillinium carboxylates and we report here the structure of 2-fluoroanilinium 2-(2-fluorophenylamino)-2-oxoacetate, (I).
The title compound (I) is built up from a 2-fluoroanilinium cation and 2-(2-fluorophenylamino)-2-oxoacetate anion (Fig. 1). There are two intramolecular hydrogen bonds which generate S(6)and S(5) motifs (Bernstein et al., 1995; Etter, 1990), and the anions and cations of (I) are linked to each other by five intermolecular hydrogen bond interactions (Table 1.). The intermolecular hydrogen interactions, except N—H···F, generate R12(5)R42(8)R44(12) motifs (Fig. 2) and these motifs link N—H···F hydrogen bonded R22(10) rings (Fig. 3) forming a three dimensional network. The dihedral angles between the aromatic ring and intramolecular hydrogen bonded rings in the anion are 2.97 (7)° and 6.70 (5)°. The two aromatic rings of the title compound are oriented with a dihedral angle of 77.25 (9)°.