(E)-1-[(2-Fluoro-phen-yl)imino-meth-yl]-2-naphthol-(Z)-1-[(2-fluoro-phen-yl)amino-methyl-idene]naphthalen-2(1H)-one (0.57/0.43).

The title Schiff base compound, 0.57C(17)H(12)FNO·0.43C(17)H(12)FNO, reveals both the enol (OH) and keto (NH) tautomeric forms with occupancies of 0.57 (6) and 0.43 (6), respectively. The tautomeric forms are stabilized by intra-molecular O-H⋯N (enol) and N-H⋯O (keto) hydrogen bonds. The dihedral angle between the naphthalene ring system and the benzene ring is 32.76 (1)°.

Related literature

For the biological properties of Schiff bases, see: Lozier et al. (1975 ▶). For the coordination chemistry of Schiff bases, see: Kargar et al. (2009 ▶); Yeap et al. (2009 ▶). For Schiff base tautomerism, see: Hökelek et al. (2000 ▶); Kaitner & Pavlovic (1996 ▶); Karabıyık et al. (2007 ▶); Nazır et al. (2000 ▶); Odabaşoğlu et al. (2005 ▶); Yıldız et al. (1998 ▶); Tanak et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

0.57C17H12FNO·0.43C17H12FNO

M = 265.28

Orthorhombic,

a = 7.2841 (3) Å

b = 12.2158 (6) Å

c = 14.5731 (7) Å

V = 1296.73 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.73 × 0.31 × 0.10 mm

Data collection

Stoe IPDSII diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.967, T max = 0.993

5655 measured reflections

1477 independent reflections

951 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.113

S = 0.97

1477 reflections

183 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.14 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/S1600536810014777/ci5080sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014777/ci5080Isup2.hkl

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

0.57C17H12FNO·0.43C17H12FNO	F(000) = 552
Mr = 265.28	Dx = 1.359 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4776 reflections
a = 7.2841 (3) Å	θ = 1.4–27.8°
b = 12.2158 (6) Å	µ = 0.10 mm−1
c = 14.5731 (7) Å	T = 296 K
V = 1296.73 (10) Å3	Needle, yellow
Z = 4	0.73 × 0.31 × 0.10 mm

Stoe IPDSII diffractometer	1477 independent reflections
Radiation source: fine-focus sealed tube	951 reflections with I > 2σ(I)
graphite	Rint = 0.040
Detector resolution: 6.67 pixels mm-1	θmax = 26.0°, θmin = 2.2°
ω scans	h = −8→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→15
Tmin = 0.967, Tmax = 0.993	l = −17→16
5655 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 0.97	w = 1/[σ2(Fo2) + (0.0576P)2] where P = (Fo2 + 2Fc2)/3
1477 reflections	(Δ/σ)max = 0.001
183 parameters	Δρmax = 0.23 e Å−3
1 restraint	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C1	0.3705 (5)	0.8439 (3)	0.5517 (2)	0.0525 (9)
C2	0.4237 (5)	0.7941 (4)	0.6359 (3)	0.0643 (10)
C3	0.4381 (5)	0.8594 (4)	0.7158 (3)	0.0736 (12)
H3	0.4738	0.8268	0.7707	0.088*
C4	0.4018 (5)	0.9661 (4)	0.7144 (3)	0.0700 (11)
H4	0.4127	1.0060	0.7685	0.084*
C5	0.3467 (5)	1.0212 (3)	0.6328 (3)	0.0614 (10)
C6	0.3091 (6)	1.1331 (4)	0.6324 (3)	0.0780 (12)
H6	0.3201	1.1728	0.6866	0.094*
C7	0.2573 (8)	1.1848 (4)	0.5552 (4)	0.0927 (14)
H7	0.2337	1.2596	0.5562	0.111*
C8	0.2390 (7)	1.1264 (4)	0.4742 (3)	0.0899 (14)
H8	0.2024	1.1621	0.4209	0.108*
C9	0.2744 (6)	1.0171 (3)	0.4721 (3)	0.0706 (11)
H9	0.2614	0.9793	0.4171	0.085*
C10	0.3302 (4)	0.9598 (3)	0.5510 (2)	0.0520 (8)
C11	0.3571 (5)	0.7794 (3)	0.4722 (2)	0.0568 (9)
H11	0.3241	0.8133	0.4175	0.068*
C12	0.3841 (5)	0.6111 (3)	0.3898 (3)	0.0577 (9)
C13	0.3368 (6)	0.5017 (3)	0.3975 (3)	0.0743 (10)
C14	0.3288 (6)	0.4347 (4)	0.3228 (5)	0.0930 (15)
H14	0.2959	0.3616	0.3296	0.112*
C15	0.3693 (7)	0.4754 (5)	0.2380 (4)	0.0916 (16)
H15	0.3627	0.4302	0.1868	0.110*
C16	0.4199 (6)	0.5835 (4)	0.2282 (3)	0.0830 (13)
H16	0.4484	0.6111	0.1704	0.100*
C17	0.4283 (5)	0.6505 (3)	0.3039 (3)	0.0689 (11)
H17	0.4642	0.7231	0.2971	0.083*
F1	0.2925 (4)	0.4629 (2)	0.4811 (2)	0.1113 (10)
N1	0.3887 (4)	0.6741 (2)	0.4711 (2)	0.0612 (8)
H1B	0.4135	0.6418	0.5220	0.073*	0.43 (6)
O1	0.4613 (5)	0.6891 (2)	0.6408 (2)	0.0823 (9)
H1A	0.4242	0.6584	0.5943	0.124*	0.57 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0475 (17)	0.062 (2)	0.048 (2)	−0.0027 (16)	−0.0010 (14)	−0.0002 (18)
C2	0.055 (2)	0.076 (3)	0.062 (3)	−0.003 (2)	0.0028 (18)	0.008 (2)
C3	0.068 (2)	0.106 (4)	0.047 (2)	0.005 (2)	0.0024 (19)	0.007 (2)
C4	0.062 (2)	0.099 (3)	0.049 (2)	−0.007 (2)	0.0014 (19)	−0.007 (2)
C5	0.055 (2)	0.072 (3)	0.057 (2)	−0.0125 (18)	0.0069 (17)	−0.010 (2)
C6	0.081 (3)	0.076 (3)	0.077 (3)	−0.012 (2)	0.015 (2)	−0.020 (3)
C7	0.118 (4)	0.057 (2)	0.103 (4)	−0.001 (3)	0.016 (3)	−0.004 (3)
C8	0.127 (4)	0.062 (3)	0.081 (3)	0.013 (3)	−0.003 (3)	0.006 (2)
C9	0.096 (3)	0.061 (2)	0.055 (2)	0.004 (2)	−0.003 (2)	0.0001 (18)
C10	0.0468 (18)	0.056 (2)	0.053 (2)	−0.0045 (15)	0.0006 (15)	0.0017 (18)
C11	0.055 (2)	0.057 (2)	0.059 (2)	0.0004 (17)	−0.0048 (18)	0.0079 (17)
C12	0.0473 (18)	0.052 (2)	0.073 (3)	0.0021 (16)	−0.0060 (18)	−0.006 (2)
C13	0.062 (2)	0.056 (3)	0.104 (2)	0.0001 (19)	−0.002 (2)	−0.005 (2)
C14	0.074 (3)	0.055 (3)	0.151 (5)	−0.001 (2)	−0.011 (3)	−0.010 (3)
C15	0.075 (3)	0.087 (4)	0.114 (4)	0.014 (3)	−0.007 (3)	−0.040 (3)
C16	0.075 (3)	0.094 (4)	0.080 (3)	0.014 (3)	0.000 (2)	−0.017 (3)
C17	0.067 (2)	0.070 (3)	0.070 (2)	0.007 (2)	0.001 (2)	−0.008 (2)
F1	0.124 (2)	0.0774 (17)	0.133 (2)	−0.0092 (16)	0.007 (2)	0.0304 (16)
N1	0.0596 (18)	0.057 (2)	0.067 (2)	0.0015 (15)	−0.0012 (15)	0.0019 (16)
O1	0.098 (2)	0.0781 (19)	0.0710 (19)	0.0091 (18)	0.0012 (16)	0.0213 (16)

C1—C11	1.405 (5)	C9—H9	0.93
C1—C2	1.424 (5)	C11—N1	1.306 (4)
C1—C10	1.446 (5)	C11—H11	0.93
C2—O1	1.314 (5)	C12—C17	1.380 (5)
C2—C3	1.415 (5)	C12—C13	1.384 (5)
C3—C4	1.330 (6)	C12—N1	1.413 (4)
C3—H3	0.93	C13—F1	1.347 (5)
C4—C5	1.426 (6)	C13—C14	1.363 (6)
C4—H4	0.93	C14—C15	1.365 (7)
C5—C6	1.394 (6)	C14—H14	0.93
C5—C10	1.413 (5)	C15—C16	1.378 (7)
C6—C7	1.344 (6)	C15—H15	0.93
C6—H6	0.93	C16—C17	1.375 (6)
C7—C8	1.387 (6)	C16—H16	0.93
C7—H7	0.93	C17—H17	0.93
C8—C9	1.360 (5)	N1—H1B	0.86
C8—H8	0.93	O1—H1A	0.82
C9—C10	1.406 (5)
C11—C1—C2	119.3 (3)	C9—C10—C1	123.5 (3)
C11—C1—C10	122.0 (3)	C5—C10—C1	119.7 (3)
C2—C1—C10	118.7 (3)	N1—C11—C1	123.4 (3)
O1—C2—C3	119.4 (4)	N1—C11—H11	118.3
O1—C2—C1	121.3 (4)	C1—C11—H11	118.3
C3—C2—C1	119.3 (4)	C17—C12—C13	117.9 (4)
C4—C3—C2	121.6 (4)	C17—C12—N1	124.4 (3)
C4—C3—H3	119.2	C13—C12—N1	117.7 (4)
C2—C3—H3	119.2	F1—C13—C14	120.0 (4)
C3—C4—C5	122.1 (4)	F1—C13—C12	118.2 (4)
C3—C4—H4	118.9	C14—C13—C12	121.8 (5)
C5—C4—H4	118.9	C13—C14—C15	119.7 (5)
C6—C5—C10	120.1 (4)	C13—C14—H14	120.2
C6—C5—C4	121.4 (4)	C15—C14—H14	120.2
C10—C5—C4	118.5 (4)	C14—C15—C16	120.1 (5)
C7—C6—C5	121.2 (4)	C14—C15—H15	120.0
C7—C6—H6	119.4	C16—C15—H15	120.0
C5—C6—H6	119.4	C17—C16—C15	119.9 (5)
C6—C7—C8	119.9 (4)	C17—C16—H16	120.0
C6—C7—H7	120.1	C15—C16—H16	120.0
C8—C7—H7	120.1	C16—C17—C12	120.7 (4)
C9—C8—C7	120.4 (4)	C16—C17—H17	119.7
C9—C8—H8	119.8	C12—C17—H17	119.7
C7—C8—H8	119.8	C11—N1—C12	122.9 (3)
C8—C9—C10	121.7 (4)	C11—N1—H1B	118.6
C8—C9—H9	119.2	C12—N1—H1B	118.6
C10—C9—H9	119.2	C2—O1—H1A	109.5
C9—C10—C5	116.7 (3)
C11—C1—C2—O1	0.3 (5)	C11—C1—C10—C9	0.3 (5)
C10—C1—C2—O1	179.8 (3)	C2—C1—C10—C9	−179.2 (4)
C11—C1—C2—C3	179.7 (3)	C11—C1—C10—C5	−179.7 (3)
C10—C1—C2—C3	−0.9 (5)	C2—C1—C10—C5	0.8 (5)
O1—C2—C3—C4	179.9 (4)	C2—C1—C11—N1	1.0 (5)
C1—C2—C3—C4	0.5 (6)	C10—C1—C11—N1	−178.5 (3)
C2—C3—C4—C5	−0.1 (6)	C17—C12—C13—F1	−179.7 (4)
C3—C4—C5—C6	180.0 (4)	N1—C12—C13—F1	2.0 (5)
C3—C4—C5—C10	0.1 (5)	C17—C12—C13—C14	−1.7 (6)
C10—C5—C6—C7	−0.1 (6)	N1—C12—C13—C14	−180.0 (4)
C4—C5—C6—C7	180.0 (4)	F1—C13—C14—C15	178.3 (4)
C5—C6—C7—C8	0.5 (8)	C12—C13—C14—C15	0.4 (6)
C6—C7—C8—C9	−0.4 (8)	C13—C14—C15—C16	0.7 (7)
C7—C8—C9—C10	0.0 (8)	C14—C15—C16—C17	−0.5 (7)
C8—C9—C10—C5	0.4 (6)	C15—C16—C17—C12	−0.9 (7)
C8—C9—C10—C1	−179.5 (4)	C13—C12—C17—C16	1.9 (6)
C6—C5—C10—C9	−0.3 (5)	N1—C12—C17—C16	−179.9 (4)
C4—C5—C10—C9	179.6 (3)	C1—C11—N1—C12	−176.7 (3)
C6—C5—C10—C1	179.6 (3)	C17—C12—N1—C11	30.5 (5)
C4—C5—C10—C1	−0.5 (5)	C13—C12—N1—C11	−151.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.82	2.535 (4)	144
N1—H1B···O1	0.86	1.86	2.535 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.82	2.535 (4)	144
N1—H1B⋯O1	0.86	1.86	2.535 (4)	134