(E)-2-[(4-Fluoro-phen-yl)imino-meth-yl]-5-methoxy-phenol.

In the mol-ecule of the title compound, C(14)H(12)FNO(2), the aromatic rings are oriented at a dihedral angle of 48.17 (1)°. An intra-molecular O-H⋯N hydrogen bond results in the formation of a six-membered ring. The title mol-ecule is a phenol-imine tautomer, as evidenced by the C-O [1.351 (3) Å], C-N [1.282 (3) Å], and C-C [1.416 (3)-1.445 (3) Å] bond lengths. In the crystal, mol-ecules are linked by inter-molecular C-H⋯π inter-actions.

Related literature

The present work is part of a structural study of Schiff bases, see: Özek et al. (2007 ▶); Odabaşoğlu et al. (2007 ▶); Albayrak et al. (2005 ▶). For related structures, see: Özek et al. (2007 ▶, 2009 ▶).

Experimental

Crystal data

C14H12FNO2

M = 245.25

Monoclinic,

a = 13.1806 (7) Å

b = 7.1785 (5) Å

c = 6.4297 (3) Å

β = 97.967 (4)°

V = 602.49 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.68 × 0.48 × 0.17 mm

Data collection

Stoe IPDS II diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.932, T max = 0.985

6287 measured reflections

1399 independent reflections

1273 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.104

S = 1.09

1399 reflections

168 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.11 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/S1600536810000474/bt5163sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000474/bt5163Isup2.hkl

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

C14H12FNO2	F(000) = 256
Mr = 245.25	Dx = 1.352 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 11108 reflections
a = 13.1806 (7) Å	θ = 1.6–28.0°
b = 7.1785 (5) Å	µ = 0.10 mm−1
c = 6.4297 (3) Å	T = 296 K
β = 97.967 (4)°	Plate, yellow
V = 602.49 (6) Å3	0.68 × 0.48 × 0.17 mm
Z = 2

Stoe IPDS II diffractometer	1399 independent reflections
Radiation source: fine-focus sealed tube	1273 reflections with I > 2σ(I)
plane graphite	Rint = 0.037
Detector resolution: 6.67 pixels mm-1	θmax = 27.6°, θmin = 2.8°
ω–scan rotation method	h = −17→17
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
Tmin = 0.932, Tmax = 0.985	l = −8→8
6287 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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0672P)2 + 0.0142P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1399 reflections	Δρmax = 0.20 e Å−3
168 parameters	Δρmin = −0.11 e Å−3
3 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: 0.022 (7)

Experimental. 237 frames, detector distance = 100 mm

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	0.67815 (17)	0.7844 (3)	0.5679 (3)	0.0430 (5)
C2	0.68722 (16)	0.7118 (3)	0.3666 (3)	0.0452 (5)
C3	0.78232 (18)	0.6912 (3)	0.3009 (4)	0.0473 (5)
H3	0.7878	0.6379	0.1711	0.057*
C4	0.86907 (16)	0.7504 (3)	0.4299 (3)	0.0448 (5)
C5	0.86142 (16)	0.8247 (3)	0.6292 (3)	0.0482 (5)
H5	0.9199	0.8648	0.7153	0.058*
C6	0.76785 (16)	0.8378 (3)	0.6958 (3)	0.0472 (5)
H6	0.7637	0.8834	0.8297	0.057*
C7	0.9809 (2)	0.6644 (5)	0.1854 (5)	0.0735 (7)
H7A	0.9579	0.5374	0.1792	0.088*
H7B	1.0525	0.6683	0.1720	0.088*
H7C	0.9429	0.7339	0.0730	0.088*
C8	0.58033 (17)	0.7980 (3)	0.6444 (3)	0.0465 (5)
H8	0.5785	0.8356	0.7822	0.056*
C9	0.40316 (17)	0.7582 (3)	0.6157 (4)	0.0456 (5)
C10	0.39603 (19)	0.6839 (3)	0.8123 (4)	0.0539 (5)
H10	0.4544	0.6382	0.8942	0.065*
C11	0.3028 (2)	0.6775 (4)	0.8871 (4)	0.0606 (6)
H11	0.2976	0.6270	1.0184	0.073*
C12	0.21810 (19)	0.7470 (4)	0.7637 (5)	0.0598 (6)
C13	0.22135 (19)	0.8207 (4)	0.5678 (4)	0.0607 (6)
H13	0.1625	0.8667	0.4877	0.073*
C14	0.31454 (17)	0.8245 (4)	0.4932 (4)	0.0522 (5)
H14	0.3185	0.8717	0.3599	0.063*
N1	0.49593 (14)	0.7598 (2)	0.5277 (3)	0.0485 (5)
O1	0.60343 (14)	0.6613 (3)	0.2332 (3)	0.0631 (5)
O2	0.96531 (13)	0.7433 (3)	0.3800 (3)	0.0561 (4)
F1	0.12629 (15)	0.7419 (3)	0.8381 (4)	0.0922 (6)
H1	0.553 (2)	0.676 (4)	0.294 (5)	0.079 (10)*

	U11	U22	U33	U12	U13	U23
C1	0.0418 (10)	0.0416 (11)	0.0453 (12)	−0.0015 (8)	0.0053 (8)	−0.0006 (8)
C2	0.0420 (11)	0.0492 (11)	0.0433 (12)	−0.0009 (8)	0.0020 (9)	−0.0016 (8)
C3	0.0479 (11)	0.0539 (12)	0.0406 (10)	−0.0011 (9)	0.0075 (8)	−0.0044 (9)
C4	0.0433 (11)	0.0459 (10)	0.0459 (12)	0.0014 (8)	0.0083 (9)	0.0045 (9)
C5	0.0439 (11)	0.0547 (11)	0.0443 (11)	−0.0041 (8)	−0.0003 (9)	−0.0031 (9)
C6	0.0493 (12)	0.0510 (11)	0.0403 (11)	−0.0007 (8)	0.0034 (9)	−0.0047 (8)
C7	0.0540 (14)	0.109 (2)	0.0612 (15)	−0.0001 (14)	0.0216 (11)	−0.0148 (14)
C8	0.0456 (11)	0.0472 (11)	0.0467 (11)	0.0012 (8)	0.0068 (9)	−0.0022 (8)
C9	0.0427 (11)	0.0453 (11)	0.0492 (12)	−0.0012 (8)	0.0073 (9)	−0.0028 (8)
C10	0.0521 (12)	0.0561 (12)	0.0527 (13)	0.0052 (10)	0.0051 (10)	0.0028 (10)
C11	0.0668 (16)	0.0630 (13)	0.0541 (13)	−0.0032 (12)	0.0158 (12)	0.0027 (11)
C12	0.0453 (13)	0.0678 (14)	0.0692 (17)	−0.0077 (10)	0.0184 (12)	−0.0090 (12)
C13	0.0435 (12)	0.0705 (15)	0.0663 (17)	−0.0007 (11)	0.0008 (11)	−0.0035 (12)
C14	0.0461 (12)	0.0593 (12)	0.0503 (13)	−0.0003 (9)	0.0041 (9)	0.0013 (10)
N1	0.0415 (10)	0.0532 (10)	0.0509 (11)	0.0016 (8)	0.0063 (8)	−0.0004 (8)
O1	0.0438 (8)	0.0922 (12)	0.0515 (9)	−0.0082 (8)	0.0007 (7)	−0.0194 (9)
O2	0.0420 (8)	0.0746 (12)	0.0529 (9)	−0.0021 (7)	0.0108 (7)	−0.0033 (8)
F1	0.0568 (10)	0.1257 (16)	0.1005 (15)	−0.0092 (10)	0.0334 (9)	−0.0025 (11)

C1—C6	1.397 (3)	C8—N1	1.282 (3)
C1—C2	1.416 (3)	C8—H8	0.9300
C1—C8	1.445 (3)	C9—C10	1.387 (3)
C2—O1	1.351 (3)	C9—C14	1.399 (3)
C2—C3	1.385 (3)	C9—N1	1.417 (3)
C3—C4	1.383 (3)	C10—C11	1.381 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—O2	1.352 (3)	C11—C12	1.371 (4)
C4—C5	1.404 (3)	C11—H11	0.9300
C5—C6	1.364 (3)	C12—F1	1.362 (3)
C5—H5	0.9300	C12—C13	1.372 (4)
C6—H6	0.9300	C13—C14	1.379 (3)
C7—O2	1.414 (3)	C13—H13	0.9300
C7—H7A	0.9600	C14—H14	0.9300
C7—H7B	0.9600	O1—H1	0.824 (19)
C7—H7C	0.9600
C6—C1—C2	117.86 (19)	N1—C8—C1	121.93 (19)
C6—C1—C8	120.22 (19)	N1—C8—H8	119.0
C2—C1—C8	121.89 (18)	C1—C8—H8	119.0
O1—C2—C3	118.2 (2)	C10—C9—C14	119.1 (2)
O1—C2—C1	120.96 (19)	C10—C9—N1	122.6 (2)
C3—C2—C1	120.86 (18)	C14—C9—N1	118.2 (2)
C4—C3—C2	119.5 (2)	C11—C10—C9	120.4 (2)
C4—C3—H3	120.3	C11—C10—H10	119.8
C2—C3—H3	120.3	C9—C10—H10	119.8
O2—C4—C3	124.8 (2)	C12—C11—C10	118.6 (3)
O2—C4—C5	114.78 (19)	C12—C11—H11	120.7
C3—C4—C5	120.4 (2)	C10—C11—H11	120.7
C6—C5—C4	119.69 (19)	F1—C12—C11	118.6 (3)
C6—C5—H5	120.2	F1—C12—C13	118.4 (3)
C4—C5—H5	120.2	C11—C12—C13	123.0 (2)
C5—C6—C1	121.6 (2)	C12—C13—C14	118.0 (2)
C5—C6—H6	119.2	C12—C13—H13	121.0
C1—C6—H6	119.2	C14—C13—H13	121.0
O2—C7—H7A	109.5	C13—C14—C9	120.8 (2)
O2—C7—H7B	109.5	C13—C14—H14	119.6
H7A—C7—H7B	109.5	C9—C14—H14	119.6
O2—C7—H7C	109.5	C8—N1—C9	119.66 (17)
H7A—C7—H7C	109.5	C2—O1—H1	108 (3)
H7B—C7—H7C	109.5	C4—O2—C7	118.77 (19)
C6—C1—C2—O1	−178.6 (2)	C14—C9—C10—C11	−0.7 (3)
C8—C1—C2—O1	3.5 (3)	N1—C9—C10—C11	−176.9 (2)
C6—C1—C2—C3	1.3 (3)	C9—C10—C11—C12	−0.4 (4)
C8—C1—C2—C3	−176.6 (2)	C10—C11—C12—F1	−179.5 (2)
O1—C2—C3—C4	176.8 (2)	C10—C11—C12—C13	0.9 (4)
C1—C2—C3—C4	−3.1 (3)	F1—C12—C13—C14	−179.7 (2)
C2—C3—C4—O2	−177.68 (19)	C11—C12—C13—C14	−0.1 (4)
C2—C3—C4—C5	2.3 (3)	C12—C13—C14—C9	−1.1 (4)
O2—C4—C5—C6	−179.79 (19)	C10—C9—C14—C13	1.5 (3)
C3—C4—C5—C6	0.2 (3)	N1—C9—C14—C13	177.9 (2)
C4—C5—C6—C1	−2.1 (3)	C1—C8—N1—C9	174.01 (17)
C2—C1—C6—C5	1.3 (3)	C10—C9—N1—C8	−40.8 (3)
C8—C1—C6—C5	179.26 (19)	C14—C9—N1—C8	143.0 (2)
C6—C1—C8—N1	176.2 (2)	C3—C4—O2—C7	−2.2 (3)
C2—C1—C8—N1	−5.9 (3)	C5—C4—O2—C7	177.8 (2)

Cg1 and Cg2 are the centroids of C1—C6 and C9—C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82 (2)	1.87 (2)	2.615 (3)	150 (3)
C6—H6···Cg1i	0.93	2.73	3.4363	133
C11—H11···Cg2ii	0.93	2.93	3.6414	134
C14—H14···Cg2iii	0.93	2.91	3.6076	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C1—C6 and C9—C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82 (2)	1.87 (2)	2.615 (3)	150 (3)
C6—H6⋯Cg1i	0.93	2.73	3.4363	133
C11—H11⋯Cg2ii	0.93	2.93	3.6414	134
C14—H14⋯Cg2iii	0.93	2.91	3.6076	133

Symmetry codes: (i) ; (ii) ; (iii) .