4-[(2-Fluoro-phen-yl)amino]-4-oxo-butanoic acid.

The crystal structure of the title compound, C(10)H(10)FNO(3), contains dimers of the asymmetric unit, with R(2) (2)(8) rings arising from inter-molecular O-H⋯O hydrogen bonding through the carboxyl-ate groups. Adjacent dimeric units are connected to each other through one N-H⋯O and two C-H⋯O inter-molecular hydrogen bonds. C-H⋯O hydrogen bonds involving the aromatic ring and the O atoms of two carboxyl-ate groups form an R(3) (3)(7) ring. The crystal structure is further stabilized by C-H⋯F inter-actions, giving rise to a three-dimensional network.

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Shah et al. (2008 ▶).

Experimental

Crystal data

C10H10FNO3

M = 211.19

Monoclinic,

a = 4.8054 (3) Å

b = 19.0399 (13) Å

c = 11.0429 (8) Å

β = 101.821 (3)°

V = 988.94 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 (2) K

0.25 × 0.15 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.989

11668 measured reflections

2550 independent reflections

1366 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.144

S = 1.01

2550 reflections

142 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.20 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/S1600536808024082/fj2135sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024082/fj2135Isup2.hkl

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

C10H10FNO3	F000 = 440
Mr = 211.19	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2550 reflections
a = 4.8054 (3) Å	θ = 2.1–28.7º
b = 19.0399 (13) Å	µ = 0.12 mm−1
c = 11.0429 (8) Å	T = 296 (2) K
β = 101.821 (3)º	Needle, colorless
V = 988.94 (12) Å3	0.25 × 0.15 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2550 independent reflections
Radiation source: fine-focus sealed tube	1366 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.038
Detector resolution: 7.4 pixels mm-1	θmax = 28.7º
T = 296(2) K	θmin = 2.1º
ω scans	h = −6→5
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −25→25
Tmin = 0.975, Tmax = 0.989	l = −14→14
11668 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) = 0.145	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.1019P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
2550 reflections	Δρmax = 0.26 e Å−3
142 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	1.0488 (3)	0.33085 (7)	0.62407 (12)	0.0777 (5)
O1	0.0318 (3)	0.56812 (8)	0.11407 (14)	0.0633 (6)
O2	0.2963 (3)	0.47537 (8)	0.09700 (14)	0.0675 (6)
O3	0.2983 (3)	0.42965 (8)	0.37996 (15)	0.0638 (6)
N1	0.7391 (3)	0.38295 (8)	0.40847 (14)	0.0419 (5)
C1	0.2503 (4)	0.52781 (10)	0.15251 (18)	0.0422 (6)
C2	0.4378 (4)	0.55192 (10)	0.26901 (19)	0.0484 (6)
C3	0.6657 (4)	0.49982 (10)	0.32502 (19)	0.0469 (6)
C4	0.5482 (3)	0.43475 (10)	0.37282 (16)	0.0400 (6)
C5	0.6718 (4)	0.31736 (9)	0.45548 (17)	0.0381 (6)
C6	0.8291 (4)	0.29162 (10)	0.56401 (18)	0.0470 (6)
C7	0.7714 (5)	0.22849 (12)	0.6121 (2)	0.0671 (8)
C8	0.5497 (5)	0.18915 (12)	0.5515 (2)	0.0681 (9)
C9	0.3881 (5)	0.21314 (11)	0.4428 (2)	0.0643 (8)
C10	0.4499 (4)	0.27661 (11)	0.39432 (19)	0.0542 (7)
H1	−0.070 (5)	0.5532 (12)	0.046 (2)	0.0759*
H1A	0.916 (4)	0.3921 (10)	0.4045 (18)	0.0503*
H2A	0.32139	0.56196	0.32903	0.0581*
H2B	0.52867	0.59543	0.25277	0.0581*
H3A	0.77241	0.48655	0.26294	0.0563*
H3B	0.79632	0.52230	0.39250	0.0563*
H7	0.88285	0.21248	0.68592	0.0805*
H8	0.50824	0.14620	0.58383	0.0817*
H9	0.23582	0.18650	0.40136	0.0771*
H10	0.34085	0.29209	0.31962	0.0650*

	U11	U22	U33	U12	U13	U23
F1	0.0646 (8)	0.0765 (9)	0.0763 (9)	−0.0227 (7)	−0.0221 (7)	0.0104 (7)
O1	0.0610 (10)	0.0615 (10)	0.0597 (10)	0.0270 (8)	−0.0055 (7)	−0.0027 (7)
O2	0.0655 (10)	0.0638 (10)	0.0645 (10)	0.0308 (8)	−0.0073 (8)	−0.0113 (8)
O3	0.0265 (7)	0.0653 (10)	0.1013 (12)	0.0009 (6)	0.0170 (7)	0.0277 (8)
N1	0.0247 (7)	0.0430 (9)	0.0571 (10)	−0.0037 (7)	0.0065 (7)	0.0100 (7)
C1	0.0396 (10)	0.0384 (11)	0.0494 (11)	0.0076 (9)	0.0113 (9)	0.0120 (9)
C2	0.0434 (10)	0.0409 (10)	0.0591 (12)	−0.0036 (9)	0.0060 (9)	0.0057 (9)
C3	0.0335 (9)	0.0497 (11)	0.0552 (12)	−0.0062 (8)	0.0034 (9)	0.0103 (9)
C4	0.0278 (8)	0.0474 (11)	0.0433 (10)	−0.0045 (8)	0.0038 (7)	0.0057 (8)
C5	0.0311 (9)	0.0373 (10)	0.0465 (10)	−0.0036 (8)	0.0094 (8)	0.0014 (8)
C6	0.0396 (10)	0.0451 (11)	0.0525 (11)	−0.0081 (9)	0.0007 (9)	0.0020 (9)
C7	0.0680 (15)	0.0628 (15)	0.0654 (14)	−0.0041 (13)	0.0018 (12)	0.0211 (12)
C8	0.0742 (16)	0.0465 (12)	0.0866 (18)	−0.0138 (12)	0.0233 (14)	0.0113 (12)
C9	0.0606 (13)	0.0506 (13)	0.0804 (16)	−0.0227 (11)	0.0114 (12)	−0.0102 (12)
C10	0.0496 (12)	0.0540 (13)	0.0551 (12)	−0.0146 (10)	0.0014 (9)	0.0000 (10)

F1—C6	1.351 (2)	C6—C7	1.365 (3)
O1—C1	1.300 (2)	C7—C8	1.361 (3)
O2—C1	1.215 (2)	C8—C9	1.368 (3)
O3—C4	1.223 (2)	C9—C10	1.379 (3)
O1—H1	0.86 (2)	C2—H2A	0.9700
N1—C4	1.350 (2)	C2—H2B	0.9700
N1—C5	1.415 (2)	C3—H3A	0.9700
N1—H1A	0.88 (2)	C3—H3B	0.9700
C1—C2	1.484 (3)	C7—H7	0.9300
C2—C3	1.513 (3)	C8—H8	0.9300
C3—C4	1.502 (3)	C9—H9	0.9300
C5—C10	1.378 (3)	C10—H10	0.9300
C5—C6	1.370 (3)
F1···N1	2.723 (2)	C6···C9vii	3.566 (3)
F1···C2i	3.357 (2)	C9···O1viii	3.402 (3)
F1···H1A	2.648 (19)	C9···C6v	3.566 (3)
F1···H2Aii	2.8200	C10···O3	3.000 (3)
F1···H2Bi	2.6100	C1···H1iii	2.68 (2)
O1···O2iii	2.664 (2)	C1···H3Av	2.9200
O1···C9iv	3.402 (3)	C4···H10	2.9100
O2···C1iii	3.396 (2)	H1···O2iii	1.81 (2)
O2···C4	3.135 (2)	H1···C1iii	2.68 (2)
O2···O1iii	2.664 (2)	H1···H1iii	2.42 (3)
O3···C3v	3.262 (2)	H1A···F1	2.648 (19)
O3···C1	3.101 (3)	H1A···O3vii	2.04 (2)
O3···N1v	2.908 (2)	H1A···H3A	2.3900
O3···C10	3.000 (3)	H1A···H3B	2.5400
O1···H9iv	2.5800	H2A···O3	2.5900
O1···H3Av	2.7400	H2A···F1ii	2.8200
O2···H8vi	2.5400	H2B···F1i	2.6100
O2···H1iii	1.81 (2)	H3A···O1vii	2.7400
O2···H3A	2.6300	H3A···O2	2.6300
O3···H1Av	2.04 (2)	H3A···O3vii	2.8100
O3···H2A	2.5900	H3A···C1vii	2.9200
O3···H3Av	2.8100	H3A···H1A	2.3900
O3···H10	2.7200	H3B···H1A	2.5400
O3···H3Bii	2.8000	H3B···O3ii	2.8000
N1···F1	2.723 (2)	H7···H10ix	2.3900
N1···O3vii	2.908 (2)	H8···O2x	2.5400
C1···O3	3.101 (3)	H9···O1viii	2.5800
C1···O2iii	3.396 (2)	H10···O3	2.7200
C2···F1i	3.357 (2)	H10···C4	2.9100
C3···O3vii	3.262 (2)	H10···H7xi	2.3900
C4···O2	3.135 (2)
C1—O1—H1	111.6 (16)	C8—C9—C10	120.3 (2)
C4—N1—C5	124.00 (15)	C5—C10—C9	120.65 (19)
C4—N1—H1A	116.6 (13)	C1—C2—H2A	109.00
C5—N1—H1A	119.3 (13)	C1—C2—H2B	109.00
O1—C1—O2	122.59 (18)	C3—C2—H2A	109.00
O1—C1—C2	114.01 (17)	C3—C2—H2B	109.00
O2—C1—C2	123.40 (18)	H2A—C2—H2B	108.00
C1—C2—C3	114.31 (16)	C2—C3—H3A	109.00
C2—C3—C4	113.08 (16)	C2—C3—H3B	109.00
N1—C4—C3	115.05 (14)	C4—C3—H3A	109.00
O3—C4—C3	122.21 (17)	C4—C3—H3B	109.00
O3—C4—N1	122.74 (17)	H3A—C3—H3B	108.00
N1—C5—C6	120.67 (17)	C6—C7—H7	120.00
N1—C5—C10	121.94 (17)	C8—C7—H7	120.00
C6—C5—C10	117.39 (17)	C7—C8—H8	120.00
C5—C6—C7	122.39 (19)	C9—C8—H8	120.00
F1—C6—C5	117.86 (17)	C8—C9—H9	120.00
F1—C6—C7	119.76 (18)	C10—C9—H9	120.00
C6—C7—C8	119.6 (2)	C5—C10—H10	120.00
C7—C8—C9	119.6 (2)	C9—C10—H10	120.00
C5—N1—C4—O3	1.1 (3)	N1—C5—C6—C7	−179.78 (19)
C5—N1—C4—C3	−179.64 (16)	C10—C5—C6—F1	179.37 (17)
C4—N1—C5—C6	−129.3 (2)	C10—C5—C6—C7	−0.5 (3)
C4—N1—C5—C10	51.4 (3)	N1—C5—C10—C9	−179.55 (19)
O1—C1—C2—C3	170.92 (17)	C6—C5—C10—C9	1.2 (3)
O2—C1—C2—C3	−9.5 (3)	F1—C6—C7—C8	179.9 (2)
C1—C2—C3—C4	−67.8 (2)	C5—C6—C7—C8	−0.3 (3)
C2—C3—C4—O3	−9.2 (3)	C6—C7—C8—C9	0.3 (4)
C2—C3—C4—N1	171.57 (16)	C7—C8—C9—C10	0.4 (4)
N1—C5—C6—F1	0.1 (3)	C8—C9—C10—C5	−1.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2iii	0.86 (2)	1.81 (2)	2.664 (2)	178 (2)
N1—H1A···O3vii	0.88 (2)	2.04 (2)	2.908 (2)	169.7 (18)
C8—H8···O2x	0.93	2.54	3.435 (3)	160
C9—H9···O1viii	0.93	2.58	3.402 (3)	147
C2—H2B···F1i	0.97	2.61	3.357 (2)	134
C2—H2A···F1ii	0.97	2.82	3.602 (2)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.86 (2)	1.81 (2)	2.664 (2)	178 (2)
N1—H1A⋯O3ii	0.88 (2)	2.04 (2)	2.908 (2)	169.7 (18)
C8—H8⋯O2iii	0.93	2.54	3.435 (3)	160
C9—H9⋯O1iv	0.93	2.58	3.402 (3)	147
C2—H2B⋯F1v	0.97	2.61	3.357 (2)	134
C2—H2A⋯F1vi	0.97	2.82	3.602 (2)	138

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .