(IUCr) 2-Fluoroanilinium N-(2-fluorophenyl)oxamate

Volume 64
Part 5
Page o808
May 2008

Received 1 April 2008
Accepted 2 April 2008
Online 4 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.053
wR = 0.168
Data-to-parameter ratio = 13.2
Details

2-Fluoroanilinium N-(2-fluorophenyl)oxamate

Orhan Büyükgüngör ^a and Mustafa Odabasoglu ^b ^*

^aDepartment of Physics, Faculty of Arts & Sciences, Ondokuz Mayis University, TR-55139 Kurupelit Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts & Sciences, Ondokuz Mayis University, TR-55139 Kurupelit Samsun, Turkey
Correspondence e-mail: orhanb@omu.edu.tr

The crystal structure of the title salt, C₆H₇FN⁺·C₈H₅FNO₃^-, exhibits intramolecular N-HO and C-HO and intermolecular N-HO and N-HF 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)°.

Related literature

For related structures see: Odabasoglu & Büyükgüngör (2006a,b,c); Büyükgüngör & Odabasoglu (2007). For ring motif details, see: Bernstein et al. (1995); Etter (1990).

Experimental

Crystal data

C₆H₇FN⁺·C₈H₅FNO₃^-
M_r = 294.26
Triclinic, $[P \overline 1]$
a = 6.7118 (9) Å
b = 9.5998 (14) Å
c = 11.7000 (16) Å
= 68.346 (11)°
= 85.791 (11)°
= 77.375 (11)°
V = 683.69 (18) Å³
Z = 2
Mo K radiation
= 0.12 mm^-1
T = 296 K
0.78 × 0.47 × 0.09 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.931, T_max = 0.988
9218 measured reflections
2684 independent reflections
2023 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.168
S = 0.81
2684 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.53 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O3	0.86	2.19	2.623 (3)	111
N1-H1F1ⁱ	0.86	2.61	3.313 (3)	140
N2-H2AO2ⁱⁱ	0.93 (3)	1.77 (3)	2.696 (3)	170 (3)
N2-H2BO3ⁱⁱⁱ	0.90 (3)	1.86 (3)	2.753 (3)	174 (3)
N2-H2CO2^iv	0.89 (3)	2.05 (3)	2.802 (3)	142 (3)
N2-H2CO1^iv	0.89 (3)	2.30 (3)	3.041 (3)	141 (3)
C6-H6O1	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.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2556 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F. 279 of the University Research Fund).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Büyükgüngör, O. & Odabasoglu, M. (2007). Acta Cryst. E63, o4376-o4377.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Odabasoglu, M. & Büyükgüngör, O. (2006a). Acta Cryst. E62, o1524-o1525.
Odabasoglu, M. & Büyükgüngör, O. (2006b). Acta Cryst. E62, o1879-o1881.
Odabasoglu, M. & Büyükgüngör, O. (2006c). Acta Cryst. E62, o4543-o4544.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic compounds