2-Fluoro-anilinium N-(2-fluoro-phenyl)oxamate.

The crystal structure of the title salt, C(6)H(7)FN(+)·C(8)H(5)FNO(3) (-), exhibits intra-molecular N-H⋯O and C-H⋯O and inter-molecular N-H⋯O and N-H⋯F hydrogen-bond inter-actions, the intra-molecular hydrogen-bond inter-actions generating S(6) and S(5) ring motifs. The dihedral angles between the aromatic ring and the intra-molecular 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 (2006 ▶); Büyükgüngör & Odabaşoğlu (2007 ▶). For ring motif details, see: Bernstein et al. (1995 ▶); Etter (1990 ▶).

Experimental

Crystal data

C6H7FN+·C8H5FNO3 −

M = 294.26

Triclinic,

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 ▶) T min = 0.931, T max = 0.988

9218 measured reflections

2684 independent reflections

2023 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 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

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C6H7FN+·C8H5FNO3–	Z = 2
Mr = 294.26	F000 = 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 = 1.9–28.1º
c = 11.7000 (16) Å	µ = 0.12 mm−1
α = 68.346 (11)º	T = 296 K
β = 85.791 (11)º	Plate, colourless
γ = 77.375 (11)º	0.78 × 0.47 × 0.09 mm
V = 683.69 (18) Å3

Stoe IPDSII diffractometer	2684 independent reflections
Monochromator: plane graphite	2023 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1	Rint = 0.040
T = 296 K	θmax = 26.0º
ω rotation method scans	θmin = 1.9º
Absorption correction: integration(X-RED32; Stoe & Cie, 2002)	h = −8→8
Tmin = 0.932, Tmax = 0.988	k = −11→11
9218 measured reflections	l = −14→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.053	w = 1/[σ2(Fo2) + (0.1051P)2 + 0.5375P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.168	(Δ/σ)max < 0.001
S = 0.81	Δρmax = 0.53 e Å−3
2684 reflections	Δρmin = −0.30 e Å−3
203 parameters	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)
Secondary atom site location: difference Fourier map

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

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) ; (ii) ; (iii) ; (iv) .