4-[(E)-(4-Fluoro-benzyl-idene)amino]-benzoic acid.

In the title compound, C(14)H(10)FNO(2), the benzene rings make a dihedral angle of 57.50 (13)°, and the molecule has an E configuration about the C=N bond. In the crystal, molecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

For the synthesis, properties and uses of 4-(benzyl­idene­amino)­benzoic acid, see: Borisova et al. (2007 ▶); Schiff (1864 ▶); Innocenzi & Lebeau (2005 ▶); Muñoz-Flores et al. (2008 ▶).

Experimental

Crystal data

C14H10FNO2

M = 243.24

Monoclinic,

a = 12.2787 (5) Å

b = 5.6264 (2) Å

c = 17.2874 (8) Å

β = 105.833 (2)°

V = 1148.99 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.23 × 0.2 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

9975 measured reflections

2002 independent reflections

1226 reflections with I > 2σ(I)

R int = 0.186

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.191

S = 1.04

2002 reflections

166 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: XSCANS (Bruker, 2000 ▶); data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052275/fj2486sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052275/fj2486Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052275/fj2486Isup3.cml

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

C14H10FNO2	F(000) = 504
Mr = 243.24	Dx = 1.406 Mg m−3
Monoclinic, P21/n	Melting point: 464 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.2787 (5) Å	Cell parameters from 4962 reflections
b = 5.6264 (2) Å	θ = 2.9–27.5°
c = 17.2874 (8) Å	µ = 0.11 mm−1
β = 105.833 (2)°	T = 293 K
V = 1148.99 (8) Å3	Prism, yellow
Z = 4	0.23 × 0.2 × 0.15 mm

Nonius KappaCCD diffractometer	1226 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.186
graphite	θmax = 25.0°, θmin = 3.7°
CCD rotation images, thick slices scans	h = −14→14
9975 measured reflections	k = −6→6
2002 independent reflections	l = −17→20

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0979P)2 + 0.0699P] where P = (Fo2 + 2Fc2)/3
2002 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.18 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.7423 (2)	0.3339 (5)	−0.03261 (18)	0.0515 (8)
H1	0.7623	0.4696	−0.0012	0.062*
C2	0.7740 (2)	0.3115 (5)	−0.10261 (19)	0.0565 (8)
H2	0.8169	0.4284	−0.1185	0.068*
C3	0.7407 (3)	0.1119 (5)	−0.14822 (19)	0.0557 (8)
C4	0.6800 (2)	−0.0683 (5)	−0.12777 (19)	0.0567 (8)
H4	0.6588	−0.2005	−0.1607	0.068*
C5	0.6511 (2)	−0.0474 (5)	−0.05617 (18)	0.0528 (7)
H5	0.6116	−0.1698	−0.0397	0.063*
C6	0.6803 (2)	0.1547 (4)	−0.00823 (17)	0.0479 (7)
C7	0.6428 (2)	0.1789 (5)	0.06460 (17)	0.0506 (7)
H7	0.6186	0.0437	0.0861	0.061*
C8	0.6104 (2)	0.3845 (4)	0.17270 (17)	0.0452 (7)
C9	0.5490 (2)	0.5794 (4)	0.1872 (2)	0.0563 (8)
H9	0.5247	0.6939	0.1474	0.068*
C10	0.5237 (2)	0.6054 (5)	0.25934 (19)	0.0534 (8)
H10	0.4824	0.7367	0.2677	0.064*
C11	0.5597 (2)	0.4361 (4)	0.32045 (17)	0.0482 (7)
C12	0.6204 (2)	0.2400 (5)	0.30522 (19)	0.0554 (8)
H12	0.6446	0.1251	0.3449	0.066*
C13	0.6449 (2)	0.2136 (5)	0.23337 (18)	0.0546 (8)
H13	0.6849	0.0808	0.2246	0.065*
C14	0.5353 (2)	0.4651 (5)	0.39801 (18)	0.0523 (8)
F1	0.77081 (18)	0.0920 (3)	−0.21809 (12)	0.0827 (7)
N1	0.64180 (18)	0.3768 (4)	0.10000 (15)	0.0530 (7)
O1	0.56240 (18)	0.3041 (4)	0.45179 (13)	0.0679 (7)
O2	0.48502 (19)	0.6570 (4)	0.41100 (13)	0.0675 (7)
H	0.487 (3)	0.678 (7)	0.4597 (9)	0.101*

	U11	U22	U33	U12	U13	U23
C1	0.0568 (16)	0.0450 (14)	0.0523 (19)	−0.0016 (12)	0.0142 (13)	−0.0017 (12)
C2	0.0623 (17)	0.0512 (15)	0.061 (2)	0.0016 (13)	0.0245 (15)	0.0098 (14)
C3	0.0649 (18)	0.0582 (17)	0.0471 (19)	0.0168 (14)	0.0206 (14)	0.0037 (14)
C4	0.0639 (17)	0.0483 (15)	0.058 (2)	0.0042 (13)	0.0177 (15)	−0.0075 (14)
C5	0.0526 (15)	0.0457 (14)	0.062 (2)	−0.0007 (12)	0.0191 (13)	0.0006 (14)
C6	0.0455 (14)	0.0456 (14)	0.0520 (19)	0.0034 (11)	0.0122 (13)	0.0026 (12)
C7	0.0508 (15)	0.0520 (15)	0.0516 (18)	−0.0003 (12)	0.0185 (13)	0.0061 (13)
C8	0.0433 (14)	0.0493 (15)	0.0436 (17)	−0.0052 (11)	0.0131 (12)	−0.0007 (12)
C9	0.0569 (16)	0.0434 (14)	0.066 (2)	0.0042 (12)	0.0116 (14)	0.0095 (13)
C10	0.0558 (16)	0.0470 (14)	0.058 (2)	0.0056 (12)	0.0165 (14)	0.0001 (13)
C11	0.0478 (14)	0.0478 (14)	0.0477 (18)	0.0006 (11)	0.0106 (12)	0.0016 (13)
C12	0.0628 (17)	0.0532 (16)	0.0474 (18)	0.0097 (13)	0.0106 (14)	0.0066 (13)
C13	0.0551 (16)	0.0503 (15)	0.056 (2)	0.0109 (12)	0.0112 (14)	0.0044 (13)
C14	0.0467 (14)	0.0511 (15)	0.056 (2)	0.0011 (13)	0.0085 (12)	−0.0023 (14)
F1	0.1162 (16)	0.0737 (12)	0.0682 (14)	0.0116 (11)	0.0420 (12)	0.0015 (10)
N1	0.0532 (14)	0.0494 (13)	0.0564 (16)	0.0016 (10)	0.0150 (11)	0.0027 (11)
O1	0.0832 (15)	0.0652 (13)	0.0558 (15)	0.0141 (11)	0.0198 (11)	0.0101 (10)
O2	0.0804 (15)	0.0660 (13)	0.0549 (15)	0.0158 (10)	0.0165 (12)	−0.0040 (11)

C1—C2	1.375 (4)	C8—C13	1.400 (4)
C1—C6	1.396 (4)	C8—N1	1.413 (4)
C1—H1	0.9300	C9—C10	1.372 (4)
C2—C3	1.369 (4)	C9—H9	0.9300
C2—H2	0.9300	C10—C11	1.402 (4)
C3—C4	1.360 (4)	C10—H10	0.9300
C3—F1	1.361 (4)	C11—C12	1.396 (4)
C4—C5	1.383 (4)	C11—C14	1.460 (4)
C4—H4	0.9300	C12—C13	1.363 (4)
C5—C6	1.395 (4)	C12—H12	0.9300
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.460 (4)	C14—O1	1.275 (4)
C7—N1	1.272 (3)	C14—O2	1.294 (3)
C7—H7	0.9300	O2—H	0.845 (10)
C8—C9	1.392 (4)
C2—C1—C6	120.6 (3)	C9—C8—N1	118.5 (2)
C2—C1—H1	119.7	C13—C8—N1	123.0 (2)
C6—C1—H1	119.7	C10—C9—C8	121.0 (3)
C3—C2—C1	118.0 (3)	C10—C9—H9	119.5
C3—C2—H2	121.0	C8—C9—H9	119.5
C1—C2—H2	121.0	C9—C10—C11	120.7 (3)
C4—C3—F1	118.0 (3)	C9—C10—H10	119.7
C4—C3—C2	124.1 (3)	C11—C10—H10	119.7
F1—C3—C2	117.9 (3)	C12—C11—C10	118.0 (3)
C3—C4—C5	117.5 (3)	C12—C11—C14	121.0 (2)
C3—C4—H4	121.2	C10—C11—C14	121.0 (2)
C5—C4—H4	121.2	C13—C12—C11	121.3 (3)
C4—C5—C6	120.9 (3)	C13—C12—H12	119.4
C4—C5—H5	119.5	C11—C12—H12	119.4
C6—C5—H5	119.5	C12—C13—C8	120.7 (3)
C5—C6—C1	118.8 (3)	C12—C13—H13	119.6
C5—C6—C7	119.9 (2)	C8—C13—H13	119.6
C1—C6—C7	121.3 (2)	O1—C14—O2	120.6 (3)
N1—C7—C6	122.9 (2)	O1—C14—C11	120.8 (2)
N1—C7—H7	118.5	O2—C14—C11	118.7 (3)
C6—C7—H7	118.5	C7—N1—C8	119.7 (2)
C9—C8—C13	118.3 (3)	C14—O2—H	114 (3)
C6—C1—C2—C3	1.6 (4)	C9—C10—C11—C12	−0.8 (4)
C1—C2—C3—C4	−1.4 (4)	C9—C10—C11—C14	178.6 (2)
C1—C2—C3—F1	179.0 (2)	C10—C11—C12—C13	0.4 (4)
F1—C3—C4—C5	179.2 (2)	C14—C11—C12—C13	−179.0 (3)
C2—C3—C4—C5	−0.3 (4)	C11—C12—C13—C8	0.5 (4)
C3—C4—C5—C6	1.9 (4)	C9—C8—C13—C12	−1.0 (4)
C4—C5—C6—C1	−1.8 (4)	N1—C8—C13—C12	174.3 (2)
C4—C5—C6—C7	176.2 (2)	C12—C11—C14—O1	−4.7 (4)
C2—C1—C6—C5	0.0 (4)	C10—C11—C14—O1	175.9 (2)
C2—C1—C6—C7	−178.0 (2)	C12—C11—C14—O2	175.7 (2)
C5—C6—C7—N1	−162.4 (3)	C10—C11—C14—O2	−3.7 (4)
C1—C6—C7—N1	15.6 (4)	C6—C7—N1—C8	−176.5 (2)
C13—C8—C9—C10	0.6 (4)	C9—C8—N1—C7	−143.9 (3)
N1—C8—C9—C10	−174.9 (2)	C13—C8—N1—C7	40.8 (4)
C8—C9—C10—C11	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H···O1i	0.85 (1)	1.79 (2)	2.601 (3)	159 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H⋯O1i	0.85 (1)	1.79 (2)	2.601 (3)	159 (4)

Symmetry code: (i) .