4-Chloro-2-[(E)-(4-fluoro-phen-yl)imino-meth-yl]phenol.

In the title Schiff base mol-ecule, C13H9ClFNO, the benzene rings are twisted slightly with respect to each other, making a dihedral angle of 7.92 (2)°. An intra-molecular O-H⋯N hydrogen bond occurs. In the crystal, an infinite chain is formed along the c-axis direction by π-π stacking inter-actions between the phenyl rings and the six-membered hydrogen-bonded ring of neighboring Schiff base ligands [centroid-centroid distances of 3.698 (2) and 3.660 (3) Å]. Neighboring chains are linked into a three-dimensional supra-molecular structure by C-H⋯O and C-H⋯F hydrogen bonds.

Related literature

For the coordination modes of Schiff base ligands with transition metals, see: Ebrahimipour et al. (2012 ▶); Guo et al. (2013 ▶). For the biological activity of Schiff base ligands, see: Sawada et al. (2001 ▶); Ma et al. (2013 ▶); Siddiqui et al. (2006 ▶).

Experimental

Crystal data

C13H9ClFNO

M = 249.66

Monoclinic,

a = 4.5140 (9) Å

b = 20.560 (4) Å

c = 12.0712 (19) Å

β = 94.153 (16)°

V = 1117.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.34 × 0.27 × 0.22 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.908, T max = 0.942

6481 measured reflections

2016 independent reflections

1143 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.153

S = 1.04

2016 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813033278/zl2572sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033278/zl2572Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813033278/zl2572Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H9ClFNO	F(000) = 512
Mr = 249.66	Dx = 1.484 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3100 reflections
a = 4.5140 (9) Å	θ = 1.7–26.0°
b = 20.560 (4) Å	µ = 0.34 mm−1
c = 12.0712 (19) Å	T = 293 K
β = 94.153 (16)°	Block, yellow
V = 1117.4 (3) Å3	0.34 × 0.27 × 0.22 mm
Z = 4

Agilent Xcalibur (Eos, Gemini) diffractometer	2016 independent reflections
Radiation source: fine-focus sealed tube	1143 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω scans	θmax = 25.2°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −5→5
Tmin = 0.908, Tmax = 0.942	k = −23→24
6481 measured reflections	l = −14→14

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0516P)2] where P = (Fo2 + 2Fc2)/3
2016 reflections	(Δ/σ)max < 0.001
155 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.23 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 > 2sigma(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	0.2601 (7)	0.22941 (16)	0.7977 (3)	0.0364 (8)
C2	0.1287 (7)	0.22602 (17)	0.6887 (3)	0.0409 (8)
C3	−0.0847 (8)	0.17908 (18)	0.6617 (3)	0.0485 (10)
H3	−0.1728	0.1772	0.5897	0.058*
C4	−0.1685 (8)	0.13523 (18)	0.7395 (3)	0.0480 (9)
H4	−0.3112	0.1038	0.7202	0.058*
C5	−0.0384 (8)	0.13834 (17)	0.8465 (3)	0.0462 (9)
C6	0.1714 (7)	0.18464 (16)	0.8761 (3)	0.0456 (9)
H6	0.2552	0.1863	0.9488	0.055*
C7	0.4848 (7)	0.27750 (17)	0.8303 (3)	0.0420 (9)
H7	0.5699	0.2772	0.9028	0.050*
C8	0.7834 (7)	0.36833 (16)	0.7949 (3)	0.0380 (8)
C9	0.8940 (7)	0.37974 (17)	0.9038 (3)	0.0477 (9)
H9	0.8310	0.3540	0.9610	0.057*
C10	1.0968 (8)	0.42908 (17)	0.9277 (3)	0.0517 (10)
H10	1.1698	0.4370	1.0005	0.062*
C11	1.1880 (8)	0.46601 (17)	0.8424 (3)	0.0487 (9)
C12	1.0866 (8)	0.45657 (18)	0.7349 (3)	0.0524 (10)
H12	1.1526	0.4824	0.6785	0.063*
C13	0.8819 (8)	0.40728 (17)	0.7116 (3)	0.0494 (10)
H13	0.8093	0.4002	0.6385	0.059*
Cl1	−0.1447 (3)	0.08228 (5)	0.94489 (9)	0.0769 (4)
F1	1.3866 (5)	0.51483 (10)	0.86620 (19)	0.0767 (7)
N1	0.5694 (6)	0.32018 (13)	0.7626 (2)	0.0407 (7)
O1	0.2061 (6)	0.26776 (13)	0.60954 (19)	0.0573 (7)
H1	0.3290	0.2937	0.6366	0.086*

	U11	U22	U33	U12	U13	U23
C1	0.0361 (18)	0.039 (2)	0.0332 (19)	0.0018 (16)	−0.0011 (15)	−0.0019 (16)
C2	0.044 (2)	0.043 (2)	0.035 (2)	−0.0010 (17)	0.0013 (16)	−0.0047 (17)
C3	0.052 (2)	0.054 (2)	0.038 (2)	0.0012 (19)	−0.0047 (18)	−0.0142 (19)
C4	0.048 (2)	0.044 (2)	0.051 (2)	−0.0036 (18)	0.0013 (19)	−0.0134 (19)
C5	0.053 (2)	0.041 (2)	0.044 (2)	−0.0051 (18)	0.0023 (18)	−0.0012 (17)
C6	0.051 (2)	0.048 (2)	0.037 (2)	0.0005 (18)	−0.0034 (17)	−0.0033 (18)
C7	0.0398 (19)	0.046 (2)	0.039 (2)	0.0023 (17)	−0.0052 (16)	−0.0055 (18)
C8	0.0378 (19)	0.036 (2)	0.039 (2)	0.0013 (15)	−0.0008 (16)	−0.0005 (17)
C9	0.052 (2)	0.048 (2)	0.043 (2)	−0.0075 (18)	0.0015 (18)	−0.0019 (18)
C10	0.059 (2)	0.049 (2)	0.045 (2)	−0.0026 (19)	−0.0100 (19)	−0.0030 (19)
C11	0.045 (2)	0.042 (2)	0.058 (3)	−0.0080 (17)	−0.0024 (19)	−0.004 (2)
C12	0.056 (2)	0.049 (2)	0.053 (2)	−0.005 (2)	0.007 (2)	0.0058 (19)
C13	0.052 (2)	0.053 (2)	0.042 (2)	0.0011 (19)	−0.0058 (18)	0.0001 (19)
Cl1	0.0965 (9)	0.0668 (8)	0.0659 (7)	−0.0274 (6)	−0.0031 (6)	0.0137 (6)
F1	0.0852 (16)	0.0563 (15)	0.0870 (17)	−0.0318 (13)	−0.0043 (13)	−0.0019 (13)
N1	0.0397 (16)	0.0414 (17)	0.0407 (17)	−0.0025 (14)	0.0010 (13)	−0.0040 (15)
O1	0.0689 (19)	0.0628 (18)	0.0385 (14)	−0.0163 (14)	−0.0068 (13)	0.0018 (14)

C1—C6	1.400 (4)	C8—C13	1.384 (4)
C1—C2	1.406 (4)	C8—C9	1.392 (4)
C1—C7	1.450 (4)	C8—N1	1.418 (4)
C2—O1	1.349 (4)	C9—C10	1.383 (5)
C2—C3	1.385 (4)	C9—H9	0.9300
C3—C4	1.374 (5)	C10—C11	1.366 (5)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.381 (5)	C11—C12	1.359 (5)
C4—H4	0.9300	C11—F1	1.362 (4)
C5—C6	1.372 (4)	C12—C13	1.386 (5)
C5—Cl1	1.747 (4)	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.276 (4)	O1—H1	0.8200
C7—H7	0.9300
C6—C1—C2	118.6 (3)	C13—C8—C9	118.5 (3)
C6—C1—C7	119.6 (3)	C13—C8—N1	116.9 (3)
C2—C1—C7	121.8 (3)	C9—C8—N1	124.6 (3)
O1—C2—C3	119.2 (3)	C10—C9—C8	120.5 (3)
O1—C2—C1	121.2 (3)	C10—C9—H9	119.8
C3—C2—C1	119.5 (3)	C8—C9—H9	119.8
C4—C3—C2	121.2 (3)	C11—C10—C9	118.8 (3)
C4—C3—H3	119.4	C11—C10—H10	120.6
C2—C3—H3	119.4	C9—C10—H10	120.6
C3—C4—C5	119.3 (3)	C12—C11—F1	118.5 (3)
C3—C4—H4	120.4	C12—C11—C10	122.8 (4)
C5—C4—H4	120.4	F1—C11—C10	118.7 (3)
C6—C5—C4	121.0 (3)	C11—C12—C13	118.1 (4)
C6—C5—Cl1	119.9 (3)	C11—C12—H12	120.9
C4—C5—Cl1	119.1 (3)	C13—C12—H12	120.9
C5—C6—C1	120.4 (3)	C8—C13—C12	121.3 (3)
C5—C6—H6	119.8	C8—C13—H13	119.3
C1—C6—H6	119.8	C12—C13—H13	119.3
N1—C7—C1	122.1 (3)	C7—N1—C8	122.3 (3)
N1—C7—H7	119.0	C2—O1—H1	109.5
C1—C7—H7	119.0

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.69	3.569 (4)	158
C10—H10···F1ii	0.93	2.67	3.481 (4)	147
O1—H1···N1	0.82	1.88	2.613 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.69	3.569 (4)	158
C10—H10⋯F1ii	0.93	2.67	3.481 (4)	147
O1—H1⋯N1	0.82	1.88	2.613 (3)	148

Symmetry codes: (i) ; (ii) .