4-Fluoro-N-(4-hy-droxy-benzyl-idene)aniline.

In the title compound, C13H10FNO, the benzene ring planes are inclined at an angle of 50.52 (8)°. A characteristic of aromatic Schiff bases with N-aryl substituents is that the terminal phenyl rings are twisted relative to the plane of the HC=N link between them. In this case, the HC=N unit makes dihedral angles of 10.6 (2) and 40.5 (2)° with the hy-droxy-benzene and fluro-benzene rings, respectively. In the crystal, O-H⋯N and C-H⋯F hydrogen bonds lead to the formation of chains along the c- and b-axis directions, respectively. C-H⋯π contacts link mol-ecules along a and these contacts combine to generate a three-dimensional network with mol-ecules stacked along the b-axis direction.

Related literature

For manufacturing and pharmaceutical applications of Schiff base compounds, see: Akkurt et al. (2013 ▶). For related structures, see: Li et al. (2008 ▶); Zhang (2010 ▶); Jothi et al., (2012a ▶,b ▶). For standard bond lengths, see: Allen et al. (1987 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10FNO

M = 215.22

Orthorhombic,

a = 11.0153 (8) Å

b = 9.8596 (7) Å

c = 9.5476 (6) Å

V = 1036.93 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.20 × 0.20 mm

Data collection

Bruker KappaCCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.971, T max = 0.980

6612 measured reflections

1430 independent reflections

1282 reflections with I > 2σ(I)

R int = 0.033

θmax = 23.4°

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.078

S = 1.11

1430 reflections

146 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814015153/sj5413sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015153/sj5413Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814015153/sj5413Isup3.cml

CCDC reference: 924015

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

C13H10FNO	F(000) = 448
Mr = 215.22	Dx = 1.379 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 7057 reflections
a = 11.0153 (8) Å	θ = 1.9–23.4°
b = 9.8596 (7) Å	µ = 0.10 mm−1
c = 9.5476 (6) Å	T = 296 K
V = 1036.93 (12) Å3	Block, colourless
Z = 4	0.30 × 0.20 × 0.20 mm

Bruker KappaCCD APEXII diffractometer	1430 independent reflections
Radiation source: fine-focus sealed tube	1282 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
ω and φ scan	θmax = 23.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.971, Tmax = 0.980	k = −10→10
6612 measured reflections	l = −10→10

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.078	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.103P] where P = (Fo2 + 2Fc2)/3
1430 reflections	(Δ/σ)max < 0.001
146 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.12 e Å−3

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	0.43955 (18)	0.3194 (2)	0.3175 (2)	0.0396 (6)
C2	0.48448 (17)	0.44366 (19)	0.2735 (3)	0.0385 (5)
H2	0.5578	0.4754	0.3091	0.046*
C3	0.42173 (17)	0.5198 (2)	0.1781 (3)	0.0385 (5)
H3	0.4526	0.6034	0.1502	0.046*
C4	0.31198 (18)	0.4740 (2)	0.1219 (2)	0.0366 (5)
C5	0.26905 (18)	0.3484 (2)	0.1656 (3)	0.0448 (6)
H5	0.1963	0.3159	0.1295	0.054*
C6	0.33162 (18)	0.2716 (2)	0.2608 (3)	0.0467 (6)
H6	0.3018	0.1873	0.2875	0.056*
C7	0.23844 (18)	0.5576 (2)	0.0292 (3)	0.0393 (5)
H7	0.1598	0.5287	0.0100	0.047*
C8	0.18716 (17)	0.7493 (2)	−0.1001 (3)	0.0371 (5)
C9	0.2246 (2)	0.8203 (2)	−0.2169 (3)	0.0462 (6)
H9	0.3051	0.8148	−0.2457	0.055*
C10	0.1439 (2)	0.8992 (2)	−0.2914 (3)	0.0546 (6)
H10	0.1687	0.9455	−0.3713	0.066*
C11	0.0271 (2)	0.9080 (2)	−0.2453 (3)	0.0561 (7)
C12	−0.0118 (2)	0.8445 (3)	−0.1267 (3)	0.0554 (7)
H12	−0.0913	0.8554	−0.0957	0.067*
C13	0.06838 (18)	0.7641 (2)	−0.0534 (3)	0.0470 (6)
H13	0.0430	0.7196	0.0274	0.056*
N1	0.27379 (14)	0.66729 (17)	−0.02753 (19)	0.0379 (4)
O1	0.49408 (13)	0.24314 (15)	0.41734 (19)	0.0509 (4)
H1	0.5637	0.2701	0.4294	0.076*
F1	−0.05262 (16)	0.98467 (18)	−0.3178 (2)	0.0888 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0291 (11)	0.0482 (13)	0.0415 (15)	0.0067 (10)	0.0037 (9)	−0.0017 (10)
C2	0.0253 (10)	0.0462 (12)	0.0441 (14)	−0.0021 (9)	−0.0006 (10)	−0.0035 (11)
C3	0.0299 (11)	0.0417 (11)	0.0438 (14)	−0.0023 (9)	0.0012 (11)	−0.0019 (10)
C4	0.0284 (11)	0.0433 (12)	0.0380 (14)	0.0013 (9)	0.0023 (9)	−0.0036 (10)
C5	0.0280 (11)	0.0515 (12)	0.0547 (16)	−0.0028 (9)	−0.0059 (10)	−0.0035 (12)
C6	0.0328 (12)	0.0468 (12)	0.0606 (17)	−0.0038 (9)	0.0004 (11)	0.0034 (12)
C7	0.0273 (10)	0.0473 (12)	0.0432 (14)	0.0004 (10)	−0.0030 (9)	−0.0087 (12)
C8	0.0312 (10)	0.0407 (11)	0.0395 (13)	0.0008 (9)	−0.0042 (10)	−0.0055 (10)
C9	0.0421 (12)	0.0463 (12)	0.0503 (16)	−0.0015 (10)	0.0065 (11)	−0.0027 (12)
C10	0.0680 (17)	0.0474 (13)	0.0483 (17)	0.0061 (11)	0.0002 (13)	0.0047 (12)
C11	0.0619 (16)	0.0514 (14)	0.0549 (18)	0.0215 (12)	−0.0119 (13)	−0.0033 (13)
C12	0.0403 (12)	0.0686 (16)	0.0574 (18)	0.0146 (12)	−0.0034 (12)	−0.0081 (14)
C13	0.0367 (12)	0.0595 (14)	0.0447 (16)	0.0075 (11)	0.0020 (10)	0.0027 (11)
N1	0.0297 (8)	0.0458 (9)	0.0383 (11)	0.0018 (8)	0.0003 (8)	−0.0037 (9)
O1	0.0353 (7)	0.0614 (9)	0.0561 (11)	−0.0015 (8)	−0.0049 (7)	0.0140 (9)
F1	0.0971 (12)	0.0911 (11)	0.0781 (12)	0.0487 (10)	−0.0175 (10)	0.0104 (10)

C1—O1	1.355 (3)	C8—C9	1.379 (3)
C1—C2	1.386 (3)	C8—C13	1.390 (3)
C1—C6	1.389 (3)	C8—N1	1.430 (3)
C2—C3	1.368 (3)	C9—C10	1.379 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.398 (3)	C10—C11	1.362 (3)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.389 (3)	C11—F1	1.350 (3)
C4—C7	1.456 (3)	C11—C12	1.363 (4)
C5—C6	1.369 (3)	C12—C13	1.378 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C7—N1	1.270 (3)	O1—H1	0.8200
C7—H7	0.9300
O1—C1—C2	123.07 (19)	C9—C8—C13	119.2 (2)
O1—C1—C6	117.74 (19)	C9—C8—N1	118.62 (18)
C2—C1—C6	119.2 (2)	C13—C8—N1	122.1 (2)
C3—C2—C1	120.44 (19)	C10—C9—C8	120.7 (2)
C3—C2—H2	119.8	C10—C9—H9	119.7
C1—C2—H2	119.8	C8—C9—H9	119.7
C2—C3—C4	121.00 (19)	C11—C10—C9	118.6 (2)
C2—C3—H3	119.5	C11—C10—H10	120.7
C4—C3—H3	119.5	C9—C10—H10	120.7
C5—C4—C3	117.9 (2)	F1—C11—C10	119.0 (3)
C5—C4—C7	119.87 (18)	F1—C11—C12	118.6 (2)
C3—C4—C7	122.09 (18)	C10—C11—C12	122.4 (2)
C6—C5—C4	121.40 (19)	C11—C12—C13	119.0 (2)
C6—C5—H5	119.3	C11—C12—H12	120.5
C4—C5—H5	119.3	C13—C12—H12	120.5
C5—C6—C1	120.1 (2)	C12—C13—C8	120.1 (2)
C5—C6—H6	119.9	C12—C13—H13	120.0
C1—C6—H6	119.9	C8—C13—H13	120.0
N1—C7—C4	124.80 (18)	C7—N1—C8	118.89 (16)
N1—C7—H7	117.6	C1—O1—H1	109.5
C4—C7—H7	117.6
O1—C1—C2—C3	−176.2 (2)	N1—C8—C9—C10	179.1 (2)
C6—C1—C2—C3	1.7 (3)	C8—C9—C10—C11	1.5 (3)
C1—C2—C3—C4	−0.7 (3)	C9—C10—C11—F1	−179.8 (2)
C2—C3—C4—C5	−0.3 (3)	C9—C10—C11—C12	1.7 (4)
C2—C3—C4—C7	174.8 (2)	F1—C11—C12—C13	178.8 (2)
C3—C4—C5—C6	0.1 (3)	C10—C11—C12—C13	−2.6 (4)
C7—C4—C5—C6	−175.1 (2)	C11—C12—C13—C8	0.4 (4)
C4—C5—C6—C1	1.0 (4)	C9—C8—C13—C12	2.6 (3)
O1—C1—C6—C5	176.2 (2)	N1—C8—C13—C12	179.8 (2)
C2—C1—C6—C5	−1.9 (3)	C4—C7—N1—C8	−171.2 (2)
C5—C4—C7—N1	−172.8 (2)	C9—C8—N1—C7	−145.9 (2)
C3—C4—C7—N1	12.2 (3)	C13—C8—N1—C7	36.9 (3)
C13—C8—C9—C10	−3.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.94	2.756 (2)	176
C9—H9···F1ii	0.93	2.61	3.263 (3)	127
C13—H13···Cgiii	0.93	2.83	3.710 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.94	2.756 (2)	176
C9—H9⋯F1ii	0.93	2.61	3.263 (3)	127
C13—H13⋯Cg iii	0.93	2.83	3.710 (3)	157

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