5-[(E)-(2-Fluoro-benzyl-idene)amino]-2-hy-droxy-benzoic acid.

In the title compound, C(14)H(10)FNO(3), the dihedral angle between the two benzene rings is 32.66 (14)°. An S(6) ring motif is formed due to an intra-molecular O-H⋯O hydrogen bond between the hy-droxy and carbonyl groups. In the crystal, mol-ecules are consolidated into dimers with R(2) (2)(8) ring motifs by pairs of O-H⋯O hydrogen bonds.

Related literature

For background and related crystal structures, see: Tahir & Shad (2010 ▶); Tahir et al. (2010a ▶,b ▶,c ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H10FNO3

M = 259.23

Monoclinic,

a = 15.5688 (16) Å

b = 4.7139 (4) Å

c = 16.2248 (16) Å

β = 92.412 (4)°

V = 1189.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.30 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.972, T max = 0.983

15880 measured reflections

2161 independent reflections

1156 reflections with I > 2σ(I)

R int = 0.079

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.01

2161 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103162X/tk2774sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103162X/tk2774Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103162X/tk2774Isup3.cml

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

C14H10FNO3	F(000) = 536
Mr = 259.23	Dx = 1.447 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1156 reflections
a = 15.5688 (16) Å	θ = 2.5–25.3°
b = 4.7139 (4) Å	µ = 0.11 mm−1
c = 16.2248 (16) Å	T = 296 K
β = 92.412 (4)°	Prism, violet
V = 1189.7 (2) Å3	0.30 × 0.22 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2161 independent reflections
Radiation source: fine-focus sealed tube	1156 reflections with I > 2σ(I)
graphite	Rint = 0.079
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.5°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→5
Tmin = 0.972, Tmax = 0.983	l = −19→19
15880 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)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.0687P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2161 reflections	Δρmax = 0.17 e Å−3
179 parameters	Δρmin = −0.16 e Å−3
0 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: 0.012 (2)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
F1	0.52929 (12)	−0.3124 (5)	0.56845 (13)	0.1012 (9)
O1	0.06399 (12)	0.7307 (4)	0.55258 (12)	0.0525 (8)
O2	0.05067 (11)	0.8698 (4)	0.42115 (11)	0.0495 (7)
O3	0.14217 (13)	0.6175 (4)	0.31108 (12)	0.0542 (8)
N1	0.28499 (15)	−0.0194 (4)	0.57191 (14)	0.0515 (9)
C1	0.08505 (17)	0.7167 (5)	0.47509 (18)	0.0417 (10)
C2	0.15088 (16)	0.5080 (5)	0.45759 (15)	0.0375 (9)
C3	0.17635 (17)	0.4699 (5)	0.37661 (17)	0.0434 (10)
C4	0.23883 (18)	0.2707 (6)	0.36048 (19)	0.0519 (11)
C5	0.27501 (17)	0.1124 (6)	0.42340 (19)	0.0514 (11)
C6	0.25157 (17)	0.1477 (5)	0.50467 (18)	0.0442 (10)
C7	0.18911 (17)	0.3435 (5)	0.52047 (17)	0.0432 (9)
C8	0.3618 (2)	−0.1094 (6)	0.57106 (19)	0.0549 (11)
C9	0.39800 (18)	−0.2991 (5)	0.63403 (18)	0.0487 (11)
C10	0.4808 (2)	−0.4013 (6)	0.6308 (2)	0.0584 (11)
C11	0.5166 (2)	−0.5910 (7)	0.6868 (2)	0.0656 (12)
C12	0.4681 (2)	−0.6790 (7)	0.7506 (2)	0.0651 (12)
C13	0.3861 (2)	−0.5771 (7)	0.7575 (2)	0.0671 (12)
C14	0.35127 (19)	−0.3924 (6)	0.70003 (19)	0.0607 (11)
H1	0.0276 (18)	0.869 (6)	0.5597 (16)	0.0630*
H3	0.1029 (18)	0.734 (6)	0.3343 (18)	0.0651*
H4	0.25617	0.24473	0.30685	0.0624*
H5	0.31634	−0.02248	0.41163	0.0618*
H7	0.17190	0.36688	0.57425	0.0518*
H8	0.39610	−0.05202	0.52858	0.0659*
H11	0.57227	−0.65780	0.68150	0.0788*
H12	0.49076	−0.80744	0.78922	0.0777*
H13	0.35381	−0.63410	0.80153	0.0803*
H14	0.29529	−0.32804	0.70528	0.0729*

	U11	U22	U33	U12	U13	U23
F1	0.0551 (12)	0.1469 (19)	0.1031 (17)	0.0089 (12)	0.0211 (12)	0.0358 (14)
O1	0.0594 (14)	0.0547 (12)	0.0440 (13)	0.0135 (10)	0.0101 (10)	−0.0004 (10)
O2	0.0534 (13)	0.0504 (12)	0.0450 (12)	0.0078 (10)	0.0043 (10)	0.0038 (10)
O3	0.0612 (14)	0.0565 (13)	0.0456 (13)	0.0044 (10)	0.0096 (10)	0.0015 (10)
N1	0.0474 (16)	0.0455 (14)	0.0613 (17)	0.0035 (12)	−0.0011 (13)	0.0003 (12)
C1	0.0439 (18)	0.0368 (15)	0.0443 (18)	−0.0081 (14)	0.0023 (15)	−0.0009 (14)
C2	0.0398 (16)	0.0336 (14)	0.0391 (17)	−0.0055 (12)	0.0034 (13)	−0.0014 (13)
C3	0.0431 (17)	0.0398 (15)	0.0476 (18)	−0.0057 (14)	0.0050 (14)	0.0029 (14)
C4	0.053 (2)	0.0519 (18)	0.0517 (19)	−0.0005 (16)	0.0132 (16)	−0.0083 (16)
C5	0.0437 (18)	0.0448 (17)	0.066 (2)	0.0021 (14)	0.0058 (16)	−0.0085 (16)
C6	0.0419 (17)	0.0376 (15)	0.0529 (19)	−0.0046 (14)	0.0009 (14)	−0.0005 (14)
C7	0.0454 (17)	0.0377 (15)	0.0469 (17)	−0.0032 (13)	0.0075 (14)	−0.0038 (13)
C8	0.049 (2)	0.0498 (17)	0.066 (2)	−0.0056 (15)	0.0025 (16)	0.0062 (16)
C9	0.0419 (18)	0.0461 (17)	0.058 (2)	0.0001 (14)	0.0006 (15)	−0.0005 (15)
C10	0.0444 (19)	0.068 (2)	0.063 (2)	−0.0011 (17)	0.0061 (17)	0.0017 (18)
C11	0.049 (2)	0.078 (2)	0.069 (2)	0.0194 (18)	−0.0075 (18)	−0.0099 (19)
C12	0.065 (2)	0.068 (2)	0.061 (2)	0.0096 (18)	−0.0120 (19)	0.0010 (17)
C13	0.056 (2)	0.085 (2)	0.060 (2)	0.0020 (19)	−0.0019 (17)	0.0117 (19)
C14	0.0460 (19)	0.069 (2)	0.067 (2)	0.0058 (17)	0.0003 (17)	0.0043 (18)

F1—C10	1.354 (4)	C8—C9	1.454 (4)
O1—C1	1.314 (3)	C9—C14	1.391 (4)
O2—C1	1.239 (3)	C9—C10	1.379 (4)
O3—C3	1.360 (3)	C10—C11	1.376 (4)
O1—H1	0.88 (3)	C11—C12	1.371 (5)
O3—H3	0.92 (3)	C12—C13	1.373 (4)
N1—C6	1.426 (3)	C13—C14	1.371 (4)
N1—C8	1.270 (4)	C4—H4	0.9300
C1—C2	1.457 (4)	C5—H5	0.9300
C2—C7	1.395 (4)	C7—H7	0.9300
C2—C3	1.400 (4)	C8—H8	0.9300
C3—C4	1.385 (4)	C11—H11	0.9300
C4—C5	1.367 (4)	C12—H12	0.9300
C5—C6	1.393 (4)	C13—H13	0.9300
C6—C7	1.373 (4)	C14—H14	0.9300
C1—O1—H1	110.7 (17)	F1—C10—C9	118.1 (3)
C3—O3—H3	103.4 (18)	F1—C10—C11	118.1 (3)
C6—N1—C8	119.3 (2)	C10—C11—C12	118.3 (3)
O1—C1—O2	121.9 (2)	C11—C12—C13	120.0 (3)
O1—C1—C2	115.2 (2)	C12—C13—C14	120.6 (3)
O2—C1—C2	122.8 (3)	C9—C14—C13	121.3 (3)
C1—C2—C3	119.9 (2)	C3—C4—H4	120.00
C3—C2—C7	119.1 (2)	C5—C4—H4	120.00
C1—C2—C7	121.0 (2)	C4—C5—H5	119.00
O3—C3—C4	117.0 (2)	C6—C5—H5	119.00
O3—C3—C2	123.4 (2)	C2—C7—H7	119.00
C2—C3—C4	119.6 (2)	C6—C7—H7	119.00
C3—C4—C5	120.0 (3)	N1—C8—H8	119.00
C4—C5—C6	121.7 (3)	C9—C8—H8	119.00
C5—C6—C7	118.2 (3)	C10—C11—H11	121.00
N1—C6—C7	117.8 (2)	C12—C11—H11	121.00
N1—C6—C5	123.8 (2)	C11—C12—H12	120.00
C2—C7—C6	121.4 (3)	C13—C12—H12	120.00
N1—C8—C9	122.4 (3)	C12—C13—H13	120.00
C10—C9—C14	116.0 (3)	C14—C13—H13	120.00
C8—C9—C10	121.6 (3)	C9—C14—H14	119.00
C8—C9—C14	122.4 (3)	C13—C14—H14	119.00
C9—C10—C11	123.7 (3)
C8—N1—C6—C5	33.0 (4)	C4—C5—C6—C7	1.4 (4)
C8—N1—C6—C7	−150.8 (3)	N1—C6—C7—C2	−177.6 (2)
C6—N1—C8—C9	−175.0 (2)	C5—C6—C7—C2	−1.3 (4)
O1—C1—C2—C3	178.2 (2)	N1—C8—C9—C10	178.1 (3)
O1—C1—C2—C7	−1.6 (3)	N1—C8—C9—C14	−0.8 (4)
O2—C1—C2—C3	−1.4 (4)	C8—C9—C10—F1	2.2 (4)
O2—C1—C2—C7	178.8 (2)	C8—C9—C10—C11	−177.0 (3)
C1—C2—C3—O3	−0.6 (4)	C14—C9—C10—F1	−178.9 (3)
C1—C2—C3—C4	−179.9 (2)	C14—C9—C10—C11	1.9 (4)
C7—C2—C3—O3	179.2 (2)	C8—C9—C14—C13	178.3 (3)
C7—C2—C3—C4	−0.1 (4)	C10—C9—C14—C13	−0.6 (4)
C1—C2—C7—C6	−179.6 (2)	F1—C10—C11—C12	179.2 (3)
C3—C2—C7—C6	0.6 (4)	C9—C10—C11—C12	−1.6 (5)
O3—C3—C4—C5	−179.1 (2)	C10—C11—C12—C13	−0.2 (5)
C2—C3—C4—C5	0.2 (4)	C11—C12—C13—C14	1.5 (5)
C3—C4—C5—C6	−0.8 (4)	C12—C13—C14—C9	−1.1 (5)
C4—C5—C6—N1	177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.88 (3)	1.77 (3)	2.642 (3)	176 (3)
O3—H3···O2	0.92 (3)	1.78 (3)	2.617 (3)	152 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.88 (3)	1.77 (3)	2.642 (3)	176 (3)
O3—H3⋯O2	0.92 (3)	1.78 (3)	2.617 (3)	152 (3)

Symmetry code: (i) .