Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 5| May 2008| Page o808
doi:10.1107/S1600536808008891

2-Fluoro­anilinium N-(2-fluoro­phenyl)oxamate

Orhan Büyükgüngöra and Mustafa Odabaşoğlub*

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

(Received 1 April 2008; accepted 2 April 2008; online 4 April 2008)

The crystal structure of the title salt, C6H7FN+·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)°.

Related literature

For related structures see: Odabaşoğlu & Büyükgüngör (2006a[Odabaşoğlu, M. & Büyükgüngör, O. (2006a). Acta Cryst. E62, o1524-o1525.],b[Odabaşoğlu, M. & Büyükgüngör, O. (2006b). Acta Cryst. E62, o1879-o1881.],c[Odabaşoğlu, M. & Büyükgüngör, O. (2006c). Acta Cryst. E62, o4543-o4544.]); Büyükgüngör & Odabaşoğlu (2007[Büyükgüngör, O. & Odabaşoğlu, M. (2007). Acta Cryst. E63, o4376-o4377.]). For ring motif details, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]); Etter (1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]).

[Scheme 1]

Experimental

Crystal data

  • C6H7FN+·C8H5FNO3−

  • Mr = 294.26

  • Triclinic, [P \overline 1]

  • a = 6.7118 (9) Å

  • b = 9.5998 (14) Å

  • c = 11.7000 (16) Å

  • α = 68.346 (11)°

  • β = 85.791 (11)°

  • γ = 77.375 (11)°

  • V = 683.69 (18) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 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[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.931, Tmax = 0.988

  • 9218 measured reflections

  • 2684 independent reflections

  • 2023 reflections with I > 2σ(I)

  • Rint = 0.040
Refinement

  • R[F2 > 2σ(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

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.30 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808008891/at2556sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008891/at2556Isup2.hkl

checkCIF report


Comment top

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)°.

Related literature top

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

Experimental top

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.

Refinement top

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).

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] 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].
[Figure 3] 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].
2-Fluoroanilinium N-(2-fluorophenyl)oxamate top
Crystal data top
C6H7FN+·C8H5FNO3−Z = 2
Mr = 294.26F(000) = 304
Triclinic, P1Dx = 1.429 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.7118 (9) ÅCell parameters from 9218 reflections
b = 9.5998 (14) Åθ = 1.9–28.1°
c = 11.7000 (16) ŵ = 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
Data collection top
Stoe IPDSII
diffractometer		2684 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus2023 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.040
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω rotation method scansh = −8→8
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		k = −11→11
Tmin = 0.932, Tmax = 0.988l = −14→14
9218 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.053H 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 reflectionsΔρmax = 0.53 e Å−3
203 parametersΔρmin = −0.30 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (7)
Crystal data top
C6H7FN+·C8H5FNO3−γ = 77.375 (11)°
Mr = 294.26V = 683.69 (18) Å3
Triclinic, P1Z = 2
a = 6.7118 (9) ÅMo Kα radiation
b = 9.5998 (14) ŵ = 0.12 mm−1
c = 11.7000 (16) ÅT = 296 K
α = 68.346 (11)°0.78 × 0.47 × 0.09 mm
β = 85.791 (11)°
Data collection top
Stoe IPDSII
diffractometer		2684 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)		2023 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.988Rint = 0.040
9218 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.168H atoms treated by a mixture of independent and constrained refinement
S = 0.81Δρmax = 0.53 e Å−3
2684 reflectionsΔρmin = −0.30 e Å−3
203 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.0927 (4)0.1895 (3)0.4566 (2)0.0500 (6)
C20.2329 (5)0.2000 (4)0.5327 (3)0.0662 (7)
C30.1793 (7)0.2559 (5)0.6239 (3)0.0882 (10)
H30.27830.25990.67350.106*
C4−0.0226 (7)0.3060 (5)0.6414 (3)0.0958 (12)
H4−0.06250.34560.70300.115*
C5−0.1675 (6)0.2980 (4)0.5682 (3)0.0826 (9)
H5−0.30500.33220.58090.099*
C6−0.1122 (4)0.2399 (3)0.4759 (2)0.0619 (7)
H6−0.21160.23470.42720.074*
C70.0672 (3)0.1176 (3)0.2757 (2)0.0452 (5)
C80.2108 (3)0.0541 (3)0.1899 (2)0.0472 (5)
C90.5179 (4)0.6758 (3)0.1045 (2)0.0592 (7)
C100.3396 (3)0.7306 (3)0.0369 (2)0.0447 (5)
C110.2088 (5)0.6328 (3)0.0524 (3)0.0625 (7)
H110.08550.66780.00950.075*
C120.2612 (6)0.4827 (4)0.1318 (3)0.0804 (9)
H120.17230.41710.14200.097*
C130.4415 (6)0.4291 (4)0.1955 (3)0.0803 (9)
H130.47630.32700.24720.096*
C140.5722 (5)0.5263 (4)0.1834 (3)0.0787 (9)
H140.69420.49150.22770.094*
N10.1682 (3)0.1288 (2)0.36637 (17)0.0496 (5)
H10.29780.09350.36920.060*
N20.2905 (3)0.8889 (2)−0.04487 (19)0.0447 (5)
O1−0.1162 (3)0.1563 (2)0.25841 (17)0.0638 (5)
O20.1240 (3)0.0321 (2)0.10956 (16)0.0587 (5)
O30.3972 (3)0.0349 (2)0.20670 (16)0.0651 (5)
F10.4339 (3)0.1515 (3)0.51255 (18)0.0919 (7)
F20.6443 (3)0.7710 (2)0.0900 (2)0.1002 (7)
H2A0.243 (5)0.946 (3)0.004 (3)0.069 (8)*
H2B0.396 (5)0.915 (3)−0.094 (3)0.064 (8)*
H2C0.187 (5)0.898 (3)−0.092 (3)0.073 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0559 (14)0.0517 (13)0.0407 (12)−0.0165 (11)0.0003 (10)−0.0118 (10)
C20.0678 (18)0.0816 (19)0.0546 (15)−0.0240 (15)−0.0014 (13)−0.0257 (14)
C30.107 (3)0.115 (3)0.0628 (19)−0.040 (2)0.0018 (18)−0.0461 (19)
C40.134 (4)0.105 (3)0.068 (2)−0.035 (2)0.020 (2)−0.051 (2)
C50.086 (2)0.090 (2)0.075 (2)−0.0135 (18)0.0180 (17)−0.0395 (18)
C60.0621 (16)0.0686 (17)0.0554 (15)−0.0137 (13)0.0054 (12)−0.0239 (13)
C70.0433 (13)0.0461 (12)0.0438 (12)−0.0093 (10)−0.0035 (9)−0.0128 (10)
C80.0418 (12)0.0501 (13)0.0448 (12)−0.0068 (10)−0.0029 (9)−0.0124 (10)
C90.0528 (15)0.0617 (16)0.0590 (15)−0.0124 (12)−0.0016 (12)−0.0166 (12)
C100.0465 (12)0.0475 (12)0.0420 (11)−0.0057 (10)0.0015 (9)−0.0211 (10)
C110.0719 (18)0.0591 (16)0.0633 (16)−0.0226 (13)−0.0022 (13)−0.0243 (13)
C120.102 (3)0.0582 (18)0.083 (2)−0.0320 (17)0.0009 (19)−0.0194 (16)
C130.102 (3)0.0503 (16)0.0728 (19)−0.0055 (16)0.0036 (18)−0.0103 (14)
C140.0662 (19)0.078 (2)0.0695 (19)0.0046 (16)−0.0092 (15)−0.0104 (16)
N10.0409 (10)0.0623 (12)0.0463 (11)−0.0105 (9)−0.0033 (8)−0.0198 (9)
N20.0391 (11)0.0510 (11)0.0458 (11)−0.0096 (8)−0.0009 (9)−0.0192 (9)
O10.0404 (10)0.0909 (14)0.0671 (11)−0.0012 (9)−0.0080 (8)−0.0420 (10)
O20.0498 (10)0.0734 (12)0.0605 (10)−0.0046 (8)−0.0034 (8)−0.0369 (9)
O30.0402 (10)0.0987 (15)0.0522 (10)−0.0088 (9)−0.0004 (7)−0.0254 (10)
F10.0653 (11)0.1443 (18)0.0815 (12)−0.0250 (11)−0.0134 (9)−0.0540 (12)
F20.0742 (12)0.0985 (15)0.1081 (15)−0.0317 (10)−0.0328 (11)−0.0010 (12)
Geometric parameters (Å, º) top
C1—C61.386 (4)C9—F21.337 (3)
C1—C21.385 (4)C9—C141.374 (4)
C1—N11.399 (3)C9—C101.375 (3)
C2—C31.356 (5)C10—C111.377 (3)
C2—F11.361 (4)C10—N21.445 (3)
C3—C41.363 (5)C11—C121.378 (4)
C3—H30.9300C11—H110.9300
C4—C51.375 (5)C12—C131.365 (5)
C4—H40.9300C12—H120.9300
C5—C61.381 (4)C13—C141.379 (5)
C5—H50.9300C13—H130.9300
C6—H60.9300C14—H140.9300
C7—O11.214 (3)N1—H10.8600
C7—N11.349 (3)N2—H2A0.93 (3)
C7—C81.536 (3)N2—H2B0.90 (3)
C8—O31.244 (3)N2—H2C0.89 (3)
C8—O21.244 (3)
C6—C1—C2117.3 (2)C14—C9—C10122.3 (3)
C6—C1—N1125.0 (2)C9—C10—C11118.4 (2)
C2—C1—N1117.7 (2)C9—C10—N2119.9 (2)
C3—C2—F1119.5 (3)C11—C10—N2121.7 (2)
C3—C2—C1123.4 (3)C12—C11—C10119.8 (3)
F1—C2—C1117.0 (2)C12—C11—H11120.1
C2—C3—C4118.7 (3)C10—C11—H11120.1
C2—C3—H3120.7C13—C12—C11120.9 (3)
C4—C3—H3120.7C13—C12—H12119.5
C3—C4—C5120.0 (3)C11—C12—H12119.5
C3—C4—H4120.0C12—C13—C14120.1 (3)
C5—C4—H4120.0C12—C13—H13120.0
C6—C5—C4121.1 (3)C14—C13—H13120.0
C6—C5—H5119.5C9—C14—C13118.5 (3)
C4—C5—H5119.5C9—C14—H14120.8
C5—C6—C1119.5 (3)C13—C14—H14120.8
C5—C6—H6120.3C7—N1—C1129.4 (2)
C1—C6—H6120.3C7—N1—H1115.3
O1—C7—N1125.5 (2)C1—N1—H1115.3
O1—C7—C8121.8 (2)C10—N2—H2A106.5 (18)
N1—C7—C8112.65 (19)C10—N2—H2B111.4 (18)
O3—C8—O2128.1 (2)H2A—N2—H2B116 (3)
O3—C8—C7116.8 (2)C10—N2—H2C106.7 (19)
O2—C8—C7115.1 (2)H2A—N2—H2C108 (3)
F2—C9—C14119.3 (3)H2B—N2—H2C108 (3)
F2—C9—C10118.4 (2)
C6—C1—C2—C30.2 (4)F2—C9—C10—C11−179.6 (2)
N1—C1—C2—C3−179.6 (3)C14—C9—C10—C112.2 (4)
C6—C1—C2—F1−179.5 (2)F2—C9—C10—N2−1.7 (4)
N1—C1—C2—F10.7 (4)C14—C9—C10—N2−179.9 (3)
F1—C2—C3—C4179.0 (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—C50.6 (6)C10—C11—C12—C130.0 (5)
C3—C4—C5—C6−0.2 (6)C11—C12—C13—C141.6 (5)
C4—C5—C6—C1−0.3 (5)F2—C9—C14—C13−178.8 (3)
C2—C1—C6—C50.2 (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—O3171.7 (2)O1—C7—N1—C1−2.4 (4)
N1—C7—C8—O3−6.3 (3)C8—C7—N1—C1175.6 (2)
O1—C7—C8—O2−6.5 (3)C6—C1—N1—C76.0 (4)
N1—C7—C8—O2175.5 (2)C2—C1—N1—C7−174.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.862.192.623 (3)111
N1—H1···F1i0.862.613.313 (3)140
N2—H2A···O2ii0.93 (3)1.77 (3)2.696 (3)170 (3)
N2—H2B···O3iii0.90 (3)1.86 (3)2.753 (3)174 (3)
N2—H2C···O2iv0.89 (3)2.05 (3)2.802 (3)142 (3)
N2—H2C···O1iv0.89 (3)2.30 (3)3.041 (3)141 (3)
C6—H6···O10.932.362.941 (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 formulaC6H7FN+·C8H5FNO3−
Mr294.26
Crystal system, space groupTriclinic, 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)
Z2
Radiation typeMo Kα
µ (mm−1)0.12
Crystal size (mm)0.78 × 0.47 × 0.09
Data collection
DiffractometerStoe IPDSII
diffractometer
Absorption correctionIntegration
(X-RED32; Stoe & Cie, 2002)
Tmin, Tmax0.932, 0.988
No. of measured, independent and
observed [I > 2σ(I)] reflections		9218, 2684, 2023
Rint0.040
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.168, 0.81
No. of reflections2684
No. of parameters203
H-atom treatmentH 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).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O30.862.192.623 (3)110.6
N1—H1···F1i0.862.613.313 (3)140.0
N2—H2A···O2ii0.93 (3)1.77 (3)2.696 (3)170 (3)
N2—H2B···O3iii0.90 (3)1.86 (3)2.753 (3)174 (3)
N2—H2C···O2iv0.89 (3)2.05 (3)2.802 (3)142 (3)
N2—H2C···O1iv0.89 (3)2.30 (3)3.041 (3)141 (3)
C6—H6···O10.932.362.941 (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).

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBüyükgüngör, O. & Odabaşoğlu, M. (2007). Acta Cryst. E63, o4376–o4377.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationEtter, M. C. (1990). Acc. Chem. Res. 23, 120–126.  CrossRef CAS Web of Science Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationOdabaşoğlu, M. & Büyükgüngör, O. (2006a). Acta Cryst. E62, o1524–o1525.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationOdabaşoğlu, M. & Büyükgüngör, O. (2006b). Acta Cryst. E62, o1879–o1881.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationOdabaşoğlu, M. & Büyükgüngör, O. (2006c). Acta Cryst. E62, o4543–o4544.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.  Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 64| Part 5| May 2008| Page o808
doi:10.1107/S1600536808008891
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS