(E)-2-(2-Fluoro-benzyl-idene)butanoic acid.

In the crystal structure of the title compound, C(11)H(11)FO(2), the methine CH forms an intra-molecular hydrogen bond with the carboxyl- O atom. The mol-ecules form dimers through hydrogen bonding between carboxyl- groups. These dimers are linked to each other by C-H⋯O contacts between the benzene and carbonyl groups of adjoining mol-ecules. In addition, there are weak inter-molecular C-H⋯F contacts.

Related literature

For related literature, see: Burns & Hagaman (1993 ▶); Burt (2004 ▶); Forgó et al. (2005 ▶); Hertog et al. (1995 ▶); Muhammad et al. (2007 ▶). For details of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C11H11FO2

M = 194.20

Monoclinic,

a = 4.1895 (4) Å

b = 17.4362 (19) Å

c = 13.8134 (15) Å

β = 96.719 (3)°

V = 1002.12 (18) Å3

Z = 4

Mo Kα radiation radiation

μ = 0.10 mm−1

T = 296 (2) K

0.25 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.935, T max = 0.958

8632 measured reflections

2981 independent reflections

1704 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.164

S = 1.04

2981 reflections

131 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007149/bv2091sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007149/bv2091Isup2.hkl

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

C11H11F1O2	F000 = 408
Mr = 194.20	Dx = 1.287 Mg m−3
Monoclinic, P21/c	Mo Kα radiation radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2981 reflections
a = 4.1895 (4) Å	θ = 2.3–30.6º
b = 17.4362 (19) Å	µ = 0.10 mm−1
c = 13.8134 (15) Å	T = 296 (2) K
β = 96.719 (3)º	Prismatic, colourless
V = 1002.12 (18) Å3	0.25 × 0.18 × 0.12 mm
Z = 4

Bruker KappaAPEXII CCD diffractometer	2981 independent reflections
Radiation source: fine-focus sealed tube	1704 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
Detector resolution: 7.2 pixels mm-1	θmax = 30.6º
T = 296(2) K	θmin = 2.3º
ω scans	h = −5→6
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −24→23
Tmin = 0.935, Tmax = 0.958	l = −19→19
8632 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)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1527P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2981 reflections	Δρmax = 0.41 e Å−3
131 parameters	Δρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
F1	0.5705 (5)	0.28288 (7)	0.22076 (10)	0.1113 (6)
O1	1.0669 (3)	0.08331 (7)	0.07503 (9)	0.0575 (4)
H1	1.104 (5)	0.0617 (11)	0.0126 (15)	0.069*
O2	0.8191 (3)	−0.02692 (7)	0.09434 (9)	0.0609 (4)
C1	0.8986 (4)	0.03770 (8)	0.12367 (11)	0.0406 (4)
C2	0.8045 (3)	0.06721 (8)	0.21699 (11)	0.0394 (4)
C3	0.8530 (4)	0.14131 (9)	0.23791 (12)	0.0443 (4)
H3	0.9555	0.1699	0.1938	0.053*
C4	0.7616 (4)	0.18258 (9)	0.32326 (11)	0.0449 (4)
C5	0.6226 (5)	0.25413 (10)	0.31195 (13)	0.0593 (5)
C6	0.5260 (6)	0.29671 (11)	0.38672 (16)	0.0705 (6)
H6	0.4286	0.3443	0.3749	0.085*
C7	0.5763 (6)	0.26755 (11)	0.47922 (15)	0.0659 (6)
H7	0.5120	0.2953	0.5311	0.079*
C8	0.7214 (5)	0.19750 (12)	0.49543 (14)	0.0691 (6)
H8	0.7586	0.1781	0.5585	0.083*
C9	0.8126 (5)	0.15554 (11)	0.41831 (13)	0.0601 (5)
H9	0.9105	0.1081	0.4304	0.072*
C10	0.6348 (4)	0.01081 (9)	0.27580 (12)	0.0458 (4)
H10A	0.4779	−0.0170	0.2319	0.055*
H10B	0.5185	0.0392	0.3209	0.055*
C11	0.8524 (5)	−0.04706 (11)	0.33354 (14)	0.0614 (5)
H11A	0.7248	−0.0808	0.3682	0.092*
H11B	1.0041	−0.0205	0.3791	0.092*
H11C	0.9657	−0.0764	0.2897	0.092*

	U11	U22	U33	U12	U13	U23
F1	0.2170 (19)	0.0646 (8)	0.0569 (8)	0.0505 (10)	0.0350 (9)	0.0161 (6)
O1	0.0854 (9)	0.0450 (7)	0.0468 (7)	−0.0124 (6)	0.0275 (6)	−0.0072 (5)
O2	0.0912 (10)	0.0434 (7)	0.0528 (7)	−0.0149 (6)	0.0288 (7)	−0.0118 (5)
C1	0.0485 (8)	0.0360 (8)	0.0382 (8)	0.0015 (6)	0.0091 (7)	0.0007 (6)
C2	0.0426 (8)	0.0401 (8)	0.0357 (7)	0.0046 (6)	0.0061 (6)	0.0003 (6)
C3	0.0549 (9)	0.0404 (8)	0.0382 (8)	0.0029 (6)	0.0085 (7)	−0.0005 (6)
C4	0.0575 (10)	0.0386 (8)	0.0393 (8)	0.0012 (7)	0.0088 (7)	−0.0041 (6)
C5	0.0947 (14)	0.0413 (9)	0.0438 (10)	0.0086 (9)	0.0156 (9)	0.0029 (7)
C6	0.1047 (17)	0.0438 (10)	0.0653 (13)	0.0165 (10)	0.0194 (12)	−0.0084 (9)
C7	0.0898 (15)	0.0588 (12)	0.0521 (11)	0.0015 (10)	0.0203 (10)	−0.0183 (9)
C8	0.0999 (16)	0.0685 (13)	0.0391 (9)	0.0122 (11)	0.0095 (10)	−0.0042 (9)
C9	0.0866 (14)	0.0525 (10)	0.0406 (9)	0.0170 (9)	0.0047 (9)	−0.0027 (8)
C10	0.0478 (9)	0.0460 (9)	0.0456 (9)	−0.0026 (7)	0.0136 (7)	−0.0018 (7)
C11	0.0694 (12)	0.0513 (10)	0.0654 (12)	−0.0014 (8)	0.0163 (10)	0.0179 (9)

F1—C5	1.350 (2)	C6—H6	0.9300
O1—C1	1.3006 (18)	C7—C8	1.371 (3)
O1—H1	0.97 (2)	C7—H7	0.9300
O2—C1	1.2301 (18)	C8—C9	1.383 (2)
C1—C2	1.483 (2)	C8—H8	0.9300
C2—C3	1.334 (2)	C9—H9	0.9300
C2—C10	1.506 (2)	C10—C11	1.521 (2)
C3—C4	1.470 (2)	C10—H10A	0.9700
C3—H3	0.9300	C10—H10B	0.9700
C4—C5	1.378 (2)	C11—H11A	0.9600
C4—C9	1.388 (2)	C11—H11B	0.9600
C5—C6	1.371 (3)	C11—H11C	0.9600
C6—C7	1.368 (3)
C1—O1—H1	112.0 (12)	C6—C7—H7	120.0
O2—C1—O1	122.15 (14)	C8—C7—H7	120.0
O2—C1—C2	120.97 (14)	C7—C8—C9	120.19 (18)
O1—C1—C2	116.88 (13)	C7—C8—H8	119.9
C3—C2—C1	118.35 (14)	C9—C8—H8	119.9
C3—C2—C10	125.80 (14)	C8—C9—C4	121.56 (17)
C1—C2—C10	115.63 (13)	C8—C9—H9	119.2
C2—C3—C4	126.91 (15)	C4—C9—H9	119.2
C2—C3—H3	116.5	C2—C10—C11	115.09 (14)
C4—C3—H3	116.5	C2—C10—H10A	108.5
C5—C4—C9	115.53 (15)	C11—C10—H10A	108.5
C5—C4—C3	119.92 (15)	C2—C10—H10B	108.5
C9—C4—C3	124.53 (14)	C11—C10—H10B	108.5
F1—C5—C6	118.18 (17)	H10A—C10—H10B	107.5
F1—C5—C4	117.52 (16)	C10—C11—H11A	109.5
C6—C5—C4	124.27 (18)	C10—C11—H11B	109.5
C7—C6—C5	118.38 (18)	H11A—C11—H11B	109.5
C7—C6—H6	120.8	C10—C11—H11C	109.5
C5—C6—H6	120.8	H11A—C11—H11C	109.5
C6—C7—C8	120.03 (18)	H11B—C11—H11C	109.5
O2—C1—C2—C3	−169.70 (16)	C3—C4—C5—C6	179.3 (2)
O1—C1—C2—C3	10.1 (2)	F1—C5—C6—C7	179.6 (2)
O2—C1—C2—C10	5.2 (2)	C4—C5—C6—C7	1.5 (4)
O1—C1—C2—C10	−174.93 (14)	C5—C6—C7—C8	0.3 (4)
C1—C2—C3—C4	176.46 (15)	C6—C7—C8—C9	−1.0 (4)
C10—C2—C3—C4	2.1 (3)	C7—C8—C9—C4	0.1 (3)
C2—C3—C4—C5	−136.30 (19)	C5—C4—C9—C8	1.5 (3)
C2—C3—C4—C9	45.5 (3)	C3—C4—C9—C8	179.80 (19)
C9—C4—C5—F1	179.57 (19)	C3—C2—C10—C11	−106.93 (19)
C3—C4—C5—F1	1.2 (3)	C1—C2—C10—C11	78.57 (19)
C9—C4—C5—C6	−2.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.97 (2)	1.66 (2)	2.6325 (18)	177.7 (12)
C3—H3···O1	0.93	2.32	2.713 (2)	105
C6—H6···O2ii	0.93	2.53	3.421 (2)	160
C8—H8···F1iii	0.93	2.55	3.266 (2)	134 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.97 (2)	1.66 (2)	2.6325 (18)	177.7 (12)
C3—H3⋯O1	0.93	2.32	2.713 (2)	105
C6—H6⋯O2ii	0.93	2.53	3.421 (2)	160
C8—H8⋯F1iii	0.93	2.55	3.266 (2)	134 (1)

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