6-Fluoro-4-oxochroman-2-carboxylic acid.

The title compound, C(10)H(7)FO(4), is an inter-mediate in the synthesis of the drug Fidarestat, (2S,4S)-2-aminoformyl-6-fluoro-spiro[chroman-4,4'-imidazolidine]-2',5'-dione. The di-hydro-pyran-one ring adopts an envelope conformation with the asymmetric C atom in the flap position. In the crystal, the mol-ecules are linked into zigzag chains along [100] by O-H⋯O hydrogen bonds and C-H⋯π inter-actions involving the benzene ring.

Related literature

Fidarestat, which shows strong inhibition to aldose reducta­ses, is used to treat complications of diabetes, see: Mealy (1996 ▶); Mitsuru et al. (2000 ▶). For related structures, see: Kurono et al. (1989 ▶); Yamaguchi et al. (1994 ▶).

Experimental

Crystal data

C10H7FO4

M = 210.16

Orthorhombic,

a = 5.3472 (11) Å

b = 12.748 (3) Å

c = 12.785 (3) Å

V = 871.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 113 K

0.28 × 0.23 × 0.22 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.962, T max = 0.970

8640 measured reflections

1212 independent reflections

1049 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.073

S = 1.12

1212 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809054555/ci2987sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809054555/ci2987Isup2.hkl

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

C10H7FO4	F(000) = 432
Mr = 210.16	Dx = 1.602 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3184 reflections
a = 5.3472 (11) Å	θ = 1.6–27.8°
b = 12.748 (3) Å	µ = 0.14 mm−1
c = 12.785 (3) Å	T = 113 K
V = 871.5 (3) Å3	Block, colourless
Z = 4	0.28 × 0.23 × 0.22 mm

Rigaku Saturn CCD area-detector diffractometer	1212 independent reflections
Radiation source: rotating anode	1049 reflections with I > 2σ(I)
confocal	Rint = 0.045
Detector resolution: 7.31 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω and φ scans	h = −7→6
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −16→16
Tmin = 0.962, Tmax = 0.970	l = −16→16
8640 measured reflections

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0448P)2] where P = (Fo2 + 2Fc2)/3
1212 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.15 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
F1	0.8260 (2)	0.32440 (8)	0.43315 (9)	0.0336 (3)
O1	0.2480 (2)	0.03466 (8)	0.23160 (9)	0.0189 (3)
O2	0.1188 (2)	0.34646 (9)	0.17373 (10)	0.0230 (3)
O3	0.5538 (2)	0.03536 (10)	0.06321 (10)	0.0230 (3)
O4	0.2609 (3)	0.11076 (10)	−0.03716 (9)	0.0250 (3)
H4	0.3799	0.1179	−0.0795	0.037*
C1	0.6806 (3)	0.25426 (12)	0.38164 (13)	0.0200 (4)
C2	0.5057 (3)	0.29048 (13)	0.31336 (12)	0.0184 (4)
H2	0.4862	0.3636	0.3015	0.022*
C3	0.3547 (3)	0.21751 (12)	0.26079 (12)	0.0152 (3)
C4	0.1561 (3)	0.25266 (12)	0.19024 (12)	0.0154 (3)
C5	−0.0026 (3)	0.16808 (13)	0.14292 (12)	0.0175 (3)
H5A	−0.0588	0.1905	0.0726	0.021*
H5B	−0.1529	0.1573	0.1868	0.021*
C6	0.1404 (3)	0.06506 (12)	0.13377 (12)	0.0167 (3)
H6	0.0182	0.0095	0.1130	0.020*
C7	0.3894 (3)	0.10981 (12)	0.27966 (12)	0.0155 (4)
C8	0.5700 (3)	0.07625 (13)	0.35030 (12)	0.0182 (4)
H8	0.5923	0.0034	0.3630	0.022*
C9	0.7161 (4)	0.14813 (12)	0.40169 (12)	0.0200 (4)
H9	0.8396	0.1257	0.4502	0.024*
C10	0.3450 (3)	0.06823 (12)	0.05065 (13)	0.0174 (3)

	U11	U22	U33	U12	U13	U23
F1	0.0418 (7)	0.0231 (5)	0.0358 (6)	−0.0017 (5)	−0.0248 (5)	−0.0041 (5)
O1	0.0218 (6)	0.0139 (5)	0.0211 (5)	−0.0031 (5)	−0.0003 (5)	0.0013 (4)
O2	0.0246 (7)	0.0158 (6)	0.0287 (6)	0.0020 (5)	−0.0091 (5)	0.0024 (5)
O3	0.0155 (6)	0.0265 (6)	0.0270 (6)	0.0037 (5)	0.0012 (5)	−0.0053 (5)
O4	0.0189 (6)	0.0340 (6)	0.0221 (6)	−0.0007 (6)	0.0050 (6)	0.0024 (5)
C1	0.0225 (10)	0.0191 (8)	0.0184 (7)	−0.0018 (7)	−0.0048 (7)	−0.0029 (7)
C2	0.0226 (10)	0.0146 (7)	0.0181 (7)	0.0007 (7)	−0.0026 (7)	−0.0004 (6)
C3	0.0155 (8)	0.0147 (7)	0.0155 (7)	0.0006 (6)	0.0004 (6)	0.0009 (6)
C4	0.0137 (8)	0.0165 (8)	0.0161 (7)	0.0007 (7)	0.0018 (6)	−0.0007 (6)
C5	0.0142 (8)	0.0182 (8)	0.0201 (8)	−0.0016 (7)	0.0011 (6)	−0.0024 (6)
C6	0.0151 (8)	0.0149 (7)	0.0201 (8)	−0.0027 (7)	0.0004 (6)	−0.0013 (6)
C7	0.0170 (9)	0.0140 (7)	0.0154 (7)	−0.0006 (7)	0.0045 (7)	−0.0012 (6)
C8	0.0226 (9)	0.0137 (7)	0.0181 (7)	0.0049 (7)	0.0033 (7)	0.0035 (6)
C9	0.0217 (9)	0.0229 (8)	0.0154 (7)	0.0042 (7)	−0.0006 (7)	0.0024 (6)
C10	0.0174 (9)	0.0133 (7)	0.0214 (8)	−0.0041 (7)	0.0010 (7)	−0.0048 (7)

F1—C1	1.3557 (18)	C3—C4	1.464 (2)
O1—C7	1.366 (2)	C4—C5	1.499 (2)
O1—C6	1.4302 (19)	C5—C6	1.524 (2)
O2—C4	1.2305 (19)	C5—H5A	0.99
O3—C10	1.203 (2)	C5—H5B	0.99
O4—C10	1.325 (2)	C6—C10	1.526 (2)
O4—H4	0.84	C6—H6	1.00
C1—C2	1.360 (2)	C7—C8	1.390 (2)
C1—C9	1.390 (2)	C8—C9	1.372 (2)
C2—C3	1.403 (2)	C8—H8	0.95
C2—H2	0.95	C9—H9	0.95
C3—C7	1.406 (2)
C7—O1—C6	115.20 (12)	H5A—C5—H5B	108.0
C10—O4—H4	109.5	O1—C6—C5	111.60 (12)
F1—C1—C2	118.84 (14)	O1—C6—C10	109.14 (14)
F1—C1—C9	118.29 (15)	C5—C6—C10	112.98 (13)
C2—C1—C9	122.87 (16)	O1—C6—H6	107.6
C1—C2—C3	118.56 (15)	C5—C6—H6	107.6
C1—C2—H2	120.7	C10—C6—H6	107.6
C3—C2—H2	120.7	O1—C7—C8	117.44 (14)
C2—C3—C7	119.28 (15)	O1—C7—C3	122.30 (15)
C2—C3—C4	120.64 (14)	C8—C7—C3	120.25 (15)
C7—C3—C4	120.03 (14)	C9—C8—C7	120.09 (15)
O2—C4—C3	121.39 (14)	C9—C8—H8	120.0
O2—C4—C5	122.54 (15)	C7—C8—H8	120.0
C3—C4—C5	116.04 (13)	C8—C9—C1	118.95 (16)
C4—C5—C6	111.51 (13)	C8—C9—H9	120.5
C4—C5—H5A	109.3	C1—C9—H9	120.5
C6—C5—H5A	109.3	O3—C10—O4	124.77 (16)
C4—C5—H5B	109.3	O3—C10—C6	124.27 (15)
C6—C5—H5B	109.3	O4—C10—C6	110.96 (14)
F1—C1—C2—C3	−179.60 (15)	C6—O1—C7—C3	24.6 (2)
C9—C1—C2—C3	−0.1 (3)	C2—C3—C7—O1	179.64 (14)
C1—C2—C3—C7	−0.4 (2)	C4—C3—C7—O1	2.1 (2)
C1—C2—C3—C4	177.15 (14)	C2—C3—C7—C8	0.5 (2)
C2—C3—C4—O2	1.2 (2)	C4—C3—C7—C8	−177.00 (14)
C7—C3—C4—O2	178.73 (16)	O1—C7—C8—C9	−179.41 (14)
C2—C3—C4—C5	−176.75 (14)	C3—C7—C8—C9	−0.3 (2)
C7—C3—C4—C5	0.8 (2)	C7—C8—C9—C1	−0.2 (2)
O2—C4—C5—C6	154.54 (16)	F1—C1—C9—C8	179.88 (15)
C3—C4—C5—C6	−27.50 (19)	C2—C1—C9—C8	0.3 (3)
C7—O1—C6—C5	−52.00 (18)	O1—C6—C10—O3	10.0 (2)
C7—O1—C6—C10	73.59 (16)	C5—C6—C10—O3	134.74 (16)
C4—C5—C6—O1	53.01 (17)	O1—C6—C10—O4	−170.78 (12)
C4—C5—C6—C10	−70.43 (17)	C5—C6—C10—O4	−46.00 (17)
C6—O1—C7—C8	−156.25 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2i	0.84	1.81	2.6474 (19)	171
C5—H5B···Cg1ii	0.99	2.51	3.4521 (19)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2i	0.84	1.81	2.6474 (19)	171
C5—H5B⋯Cg1ii	0.99	2.51	3.4521 (19)	160

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C1–C3/C7–C9 ring.