4-Fluoro-2-[(3-methyl-phen-yl)imino-meth-yl]phenol.

The title compound, C(14)H(12)FNO, crystallizes as the trans phenol-imine tautomer. The two benzene rings are essentially coplanar, being inclined to one another by 9.28 (7)°. This is at least in part due to the intra-molecular O-H⋯N hydrogen bond between the hy-droxy O atom and the imine N atom. The crystal structure is stabilized by an array of weak C-H⋯O and C-H⋯F inter-actions, which link the mol-ecules into a stable three-dimensional network.

Related literature

For related structures, see: Karakaş et al. (2004 ▶); Arod et al. (2005 ▶); Cheng et al. (2005 ▶); Brink et al. (2009 ▶). For related rhenium tricarbonyl complexes containing salicylaldimines, see: Brink et al. (2011 ▶). For related N,O-bidentate ligands coordinated to a rhenium tricarbonyl core, see: Schutte et al. (2011 ▶).

Experimental

Crystal data

C14H12FNO

M = 229.25

Monoclinic,

a = 10.2655 (6) Å

b = 4.6738 (2) Å

c = 12.3561 (8) Å

β = 112.331 (3)°

V = 548.37 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.19 × 0.1 × 0.06 mm

Data collection

Bruker X8 APEXII 4K Kappa CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.981, T max = 0.994

7009 measured reflections

1319 independent reflections

1203 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.06

1319 reflections

156 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2004 ▶); software used to prepare material for publication: WingGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010513/sj5208sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010513/sj5208Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010513/sj5208Isup3.cml

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

C14H12FNO	F(000) = 240
Mr = 229.25	Dx = 1.388 Mg m−3
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 2573 reflections
a = 10.2655 (6) Å	θ = 3.4–28.3°
b = 4.6738 (2) Å	µ = 0.10 mm−1
c = 12.3561 (8) Å	T = 100 K
β = 112.331 (3)°	Cuboid, orange
V = 548.37 (5) Å3	0.19 × 0.1 × 0.06 mm
Z = 2

Bruker X8 APEXII 4K Kappa CCD diffractometer	1319 independent reflections
Graphite monochromator	1203 reflections with I > 2σ(I)
Detector resolution: 512 pixels mm-1	Rint = 0.028
ω and φ scans	θmax = 28.0°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −13→13
Tmin = 0.981, Tmax = 0.994	k = −5→6
7009 measured reflections	l = −16→16

Refinement on F2	2 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0597P)2 + 0.0513P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.095	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.19 e Å−3
1319 reflections	Δρmin = −0.19 e Å−3
156 parameters

Experimental. Intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 55 s/frame. A total of 1495 frames were collected with a frame width of 0.5° covering up to θ = 28.0° with 99.6% completeness accomplished

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.

	x	y	z	Uiso*/Ueq
N1	0.51676 (18)	0.7931 (4)	0.51611 (15)	0.0170 (4)
O1	0.62483 (16)	0.5330 (3)	0.71672 (14)	0.0229 (4)
H1B	0.571	0.6442	0.666	0.034*
F1	0.95777 (14)	−0.0665 (3)	0.54083 (13)	0.0276 (3)
C1	0.5962 (2)	0.6410 (4)	0.47953 (19)	0.0178 (4)
H1A	0.5897	0.6626	0.4012	0.021*
C11	0.6955 (2)	0.4372 (4)	0.55563 (18)	0.0161 (4)
C12	0.7069 (2)	0.3900 (4)	0.67131 (18)	0.0183 (4)
C13	0.8048 (2)	0.1934 (5)	0.74184 (18)	0.0211 (5)
H13	0.8132	0.1637	0.8203	0.025*
C14	0.8897 (2)	0.0416 (5)	0.6980 (2)	0.0219 (5)
H14	0.9567	−0.0919	0.7458	0.026*
C15	0.8756 (2)	0.0873 (4)	0.5839 (2)	0.0195 (5)
C16	0.7817 (2)	0.2812 (5)	0.51227 (19)	0.0181 (4)
H16	0.7753	0.3092	0.4343	0.022*
C21	0.4220 (2)	0.9970 (4)	0.44138 (18)	0.0168 (4)
C22	0.3265 (2)	1.1211 (4)	0.48298 (18)	0.0171 (4)
H22	0.3286	1.0669	0.5577	0.021*
C23	0.2280 (2)	1.3232 (5)	0.41733 (18)	0.0189 (4)
C24	0.2290 (2)	1.4038 (5)	0.30877 (18)	0.0209 (5)
H24	0.163	1.541	0.2625	0.025*
C25	0.3257 (2)	1.2853 (5)	0.26779 (19)	0.0223 (5)
H25	0.3258	1.3445	0.1943	0.027*
C26	0.4219 (2)	1.0818 (4)	0.33261 (19)	0.0205 (5)
H26	0.4871	1.0008	0.3036	0.025*
C231	0.1250 (2)	1.4526 (5)	0.4626 (2)	0.0227 (5)
H23A	0.1367	1.3641	0.5377	0.034*
H23B	0.0289	1.4194	0.4063	0.034*
H23C	0.1422	1.6588	0.4736	0.034*

	U11	U22	U33	U12	U13	U23
N1	0.0165 (8)	0.0168 (8)	0.0174 (9)	−0.0004 (6)	0.0061 (7)	0.0005 (6)
O1	0.0264 (8)	0.0271 (8)	0.0181 (7)	0.0081 (6)	0.0116 (7)	0.0032 (6)
F1	0.0278 (7)	0.0264 (7)	0.0320 (7)	0.0092 (5)	0.0154 (6)	0.0010 (6)
C1	0.0200 (10)	0.0174 (8)	0.0165 (10)	−0.0022 (8)	0.0075 (8)	0.0011 (8)
C11	0.0166 (10)	0.0141 (9)	0.0164 (10)	−0.0015 (7)	0.0050 (8)	−0.0008 (8)
C12	0.0190 (10)	0.0193 (10)	0.0170 (10)	−0.0024 (8)	0.0074 (9)	−0.0012 (8)
C13	0.0228 (11)	0.0231 (10)	0.0157 (10)	−0.0005 (9)	0.0053 (9)	0.0034 (8)
C14	0.0201 (11)	0.0207 (10)	0.0212 (11)	0.0009 (8)	0.0036 (9)	0.0019 (8)
C15	0.0166 (10)	0.0191 (10)	0.0244 (12)	0.0003 (8)	0.0096 (9)	−0.0018 (8)
C16	0.0194 (10)	0.0192 (10)	0.0178 (10)	−0.0010 (8)	0.0095 (8)	−0.0006 (7)
C21	0.0171 (10)	0.0154 (9)	0.0177 (10)	−0.0020 (8)	0.0063 (8)	−0.0010 (7)
C22	0.0184 (10)	0.0163 (9)	0.0165 (10)	−0.0023 (7)	0.0066 (8)	−0.0006 (8)
C23	0.0168 (10)	0.0188 (10)	0.0200 (11)	−0.0025 (8)	0.0059 (8)	−0.0034 (8)
C24	0.0181 (11)	0.0193 (10)	0.0219 (11)	0.0017 (8)	0.0039 (9)	0.0011 (8)
C25	0.0240 (12)	0.0248 (11)	0.0186 (10)	0.0027 (8)	0.0086 (9)	0.0038 (8)
C26	0.0206 (10)	0.0217 (10)	0.0209 (11)	0.0022 (8)	0.0098 (9)	0.0001 (8)
C231	0.0192 (10)	0.0244 (10)	0.0247 (11)	0.0015 (8)	0.0086 (9)	−0.0019 (9)

N1—C1	1.287 (3)	C21—C22	1.395 (3)
N1—C21	1.422 (3)	C21—C26	1.401 (3)
O1—C12	1.353 (3)	C21—N1	1.422 (3)
O1—H1B	0.84	C22—C23	1.396 (3)
F1—C15	1.361 (2)	C22—H22	0.95
C1—C11	1.450 (3)	C23—C24	1.397 (3)
C1—H1A	0.95	C23—C231	1.499 (3)
C11—C16	1.401 (3)	C24—C25	1.389 (3)
C11—C12	1.407 (3)	C24—H24	0.95
C12—C13	1.396 (3)	C25—C26	1.386 (3)
C13—C14	1.385 (3)	C25—H25	0.95
C13—H13	0.95	C26—H26	0.95
C14—C15	1.377 (3)	C231—H23A	0.98
C14—H14	0.95	C231—H23B	0.98
C15—C16	1.373 (3)	C231—H23C	0.98
C16—H16	0.95
C1—N1—C21	120.69 (16)	C26—C21—N1	124.30 (18)
C12—O1—H1B	109.5	C22—C21—N1	116.25 (17)
N1—C1—C11	121.23 (18)	C26—C21—N1	124.30 (18)
N1—C1—H1A	119.4	C21—C22—C23	121.53 (18)
C11—C1—H1A	119.4	C21—C22—H22	119.2
C16—C11—C12	119.11 (19)	C23—C22—H22	119.2
C16—C11—C1	118.98 (18)	C22—C23—C24	118.16 (18)
C12—C11—C1	121.91 (18)	C22—C23—C231	120.94 (18)
O1—C12—C13	118.70 (18)	C24—C23—C231	120.90 (19)
O1—C12—C11	121.31 (19)	C25—C24—C23	120.63 (19)
C13—C12—C11	119.99 (19)	C25—C24—H24	119.7
C14—C13—C12	120.27 (19)	C23—C24—H24	119.7
C14—C13—H13	119.9	C26—C25—C24	120.94 (19)
C12—C13—H13	119.9	C26—C25—H25	119.5
C15—C14—C13	118.9 (2)	C24—C25—H25	119.5
C15—C14—H14	120.5	C25—C26—C21	119.3 (2)
C13—C14—H14	120.5	C25—C26—H26	120.4
F1—C15—C16	118.91 (19)	C21—C26—H26	120.4
F1—C15—C14	118.57 (19)	C23—C231—H23A	109.5
C16—C15—C14	122.5 (2)	C23—C231—H23B	109.5
C15—C16—C11	119.17 (19)	H23A—C231—H23B	109.5
C15—C16—H16	120.4	C23—C231—H23C	109.5
C11—C16—H16	120.4	H23A—C231—H23C	109.5
C22—C21—C26	119.44 (19)	H23B—C231—H23C	109.5
C22—C21—N1	116.25 (17)
N1—N1—C1—C11	0.0 (6)	N1—N1—C21—C22	0.0 (6)
C21—N1—C1—C11	178.58 (17)	C1—N1—C21—C22	171.08 (18)
N1—C1—C11—C16	−178.66 (18)	N1—N1—C21—C26	0.0 (7)
N1—C1—C11—C12	1.9 (3)	C1—N1—C21—C26	−10.4 (3)
C16—C11—C12—O1	−179.24 (18)	C1—N1—C21—N1	0E1 (10)
C1—C11—C12—O1	0.2 (3)	C26—C21—C22—C23	1.7 (3)
C16—C11—C12—C13	1.1 (3)	N1—C21—C22—C23	−179.74 (17)
C1—C11—C12—C13	−179.45 (19)	N1—C21—C22—C23	−179.74 (17)
O1—C12—C13—C14	179.49 (19)	C21—C22—C23—C24	−1.3 (3)
C11—C12—C13—C14	−0.8 (3)	C21—C22—C23—C231	179.38 (19)
C12—C13—C14—C15	−0.2 (3)	C22—C23—C24—C25	0.0 (3)
C13—C14—C15—F1	−178.87 (18)	C231—C23—C24—C25	179.33 (19)
C13—C14—C15—C16	1.0 (3)	C23—C24—C25—C26	0.9 (3)
F1—C15—C16—C11	179.14 (17)	C24—C25—C26—C21	−0.5 (3)
C14—C15—C16—C11	−0.8 (3)	C22—C21—C26—C25	−0.7 (3)
C12—C11—C16—C15	−0.3 (3)	N1—C21—C26—C25	−179.19 (19)
C1—C11—C16—C15	−179.79 (18)	N1—C21—C26—C25	−179.19 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N1	0.84	1.85	2.601 (2)	147
C1—H1A···O1i	0.95	2.6	3.467 (3)	151
C16—H16···O1i	0.95	2.65	3.495 (3)	149
C13—H13···F1ii	0.95	2.6	3.472 (3)	153
C231—H23A···F1iii	0.98	2.73	3.321 (3)	119
C231—H23C···F1iv	0.98	2.67	3.193 (2)	114

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1B⋯N1	0.84	1.85	2.601 (2)	147
C1—H1A⋯O1i	0.95	2.6	3.467 (3)	151
C16—H16⋯O1i	0.95	2.65	3.495 (3)	149
C13—H13⋯F1ii	0.95	2.6	3.472 (3)	153
C231—H23A⋯F1iii	0.98	2.73	3.321 (3)	119
C231—H23C⋯F1iv	0.98	2.67	3.193 (2)	114

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