6-De-oxy-6-fluoro-d-galactose.

The crystal structure unequivocally confirms the relative stereochemistry of the title compound, C(6)H(11)FO(5). The absolute stereochemistry was determined by the use of d-galactose as the starting material. The compound exists as a three-dimensional O-H⋯O hydrogen-bonded network with each mol-ecule acting as a donor and acceptor for four hydrogen bonds.

Related literature

For literature relating to the biotechnological inter­conversion of carbohydrates (Izumoring), see: Granström et al. (2004 ▶); Izumori (2006 ▶); Jones et al. (2008 ▶); Rao et al. (2009 ▶); Jenkinson et al. (2009 ▶); Gullapalli et al. (2010 ▶). For literature relating to fluoro­sugars, see: Cobb et al. (2005 ▶); Caravano et al. (2009 ▶); Brackhagen et al. (2001 ▶); Taylor & Kent (1958 ▶).

Experimental

Crystal data

C6H11FO5

M = 182.15

Orthorhombic,

a = 6.7928 (3) Å

b = 7.5822 (3) Å

c = 14.1165 (6) Å

V = 727.06 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.16 mm−1

T = 150 K

0.25 × 0.15 × 0.15 mm

Data collection

Area diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.88, T max = 0.98

6912 measured reflections

978 independent reflections

855 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.119

S = 1.00

978 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Nonius, 2001 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810016612/lh5035sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016612/lh5035Isup2.hkl

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

C6H11FO5	F(000) = 384
Mr = 182.15	Dx = 1.664 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 976 reflections
a = 6.7928 (3) Å	θ = 5–27°
b = 7.5822 (3) Å	µ = 0.16 mm−1
c = 14.1165 (6) Å	T = 150 K
V = 727.06 (5) Å3	Plate, colourless
Z = 4	0.25 × 0.15 × 0.15 mm

Area diffractometer	855 reflections with I > 2σ(I)
graphite	Rint = 0.082
ω scans	θmax = 27.4°, θmin = 5.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −8→8
Tmin = 0.88, Tmax = 0.98	k = −9→9
6912 measured reflections	l = −18→18
978 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.119	Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.06P)2 + 0.71P], where P = [max(Fo2,0) + 2Fc2]/3
S = 1.00	(Δ/σ)max = 0.0002
978 reflections	Δρmax = 0.39 e Å−3
109 parameters	Δρmin = −0.33 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
F1	0.9642 (3)	0.0074 (3)	0.67642 (15)	0.0322
C2	0.8064 (5)	0.1203 (4)	0.7000 (2)	0.0241
C3	0.8368 (5)	0.2957 (4)	0.6533 (2)	0.0197
O4	0.8221 (3)	0.2665 (3)	0.55221 (14)	0.0197
C5	0.8651 (5)	0.4205 (4)	0.4981 (2)	0.0199
O6	1.0586 (3)	0.4776 (3)	0.51563 (17)	0.0249
C7	0.7217 (5)	0.5681 (4)	0.5230 (2)	0.0193
O8	0.7765 (3)	0.7197 (3)	0.46922 (16)	0.0253
C9	0.7242 (5)	0.6033 (4)	0.6292 (2)	0.0196
C10	0.6857 (5)	0.4332 (4)	0.6843 (2)	0.0207
O11	0.4899 (3)	0.3738 (3)	0.66532 (15)	0.0234
O12	0.5874 (3)	0.7379 (3)	0.65554 (15)	0.0225
H21	0.6889	0.0662	0.6738	0.0302*
H22	0.7979	0.1319	0.7701	0.0295*
H31	0.9723	0.3377	0.6670	0.0229*
H51	0.8463	0.3902	0.4278	0.0240*
H71	0.5858	0.5333	0.5064	0.0246*
H91	0.8539	0.6454	0.6460	0.0234*
H101	0.7044	0.4557	0.7541	0.0250*
H121	0.4980	0.7488	0.6170	0.0346*
H111	0.4489	0.3361	0.7175	0.0347*
H61	1.1320	0.3983	0.4931	0.0374*
H81	0.7170	0.8119	0.4811	0.0389*

	U11	U22	U33	U12	U13	U23
F1	0.0339 (11)	0.0274 (10)	0.0352 (11)	0.0100 (9)	0.0011 (9)	0.0051 (9)
C2	0.0227 (16)	0.0222 (15)	0.0273 (15)	0.0057 (15)	0.0012 (14)	0.0016 (13)
C3	0.0187 (14)	0.0211 (14)	0.0193 (14)	0.0019 (13)	0.0003 (12)	0.0014 (12)
O4	0.0221 (11)	0.0165 (10)	0.0205 (10)	−0.0024 (9)	0.0011 (9)	0.0005 (9)
C5	0.0189 (15)	0.0168 (14)	0.0241 (14)	−0.0029 (12)	0.0029 (12)	0.0020 (12)
O6	0.0193 (12)	0.0195 (10)	0.0359 (12)	0.0006 (9)	0.0060 (10)	−0.0002 (9)
C7	0.0205 (16)	0.0171 (14)	0.0204 (14)	0.0006 (12)	0.0028 (12)	0.0018 (12)
O8	0.0307 (12)	0.0176 (10)	0.0277 (11)	0.0021 (10)	0.0077 (10)	0.0035 (9)
C9	0.0172 (15)	0.0171 (14)	0.0246 (15)	0.0033 (13)	0.0001 (12)	−0.0020 (12)
C10	0.0192 (16)	0.0228 (15)	0.0203 (14)	0.0005 (13)	−0.0016 (12)	0.0012 (12)
O11	0.0185 (11)	0.0281 (12)	0.0236 (11)	−0.0034 (10)	0.0013 (9)	0.0023 (10)
O12	0.0220 (11)	0.0230 (11)	0.0226 (10)	0.0054 (10)	−0.0005 (9)	−0.0038 (10)

F1—C2	1.412 (4)	C7—O8	1.428 (4)
C2—C3	1.499 (4)	C7—C9	1.522 (4)
C2—H21	0.971	C7—H71	0.988
C2—H22	0.995	O8—H81	0.824
C3—O4	1.448 (3)	C9—C10	1.528 (4)
C3—C10	1.527 (4)	C9—O12	1.430 (4)
C3—H31	0.992	C9—H91	0.967
O4—C5	1.426 (4)	C10—O11	1.430 (4)
C5—O6	1.406 (4)	C10—H101	1.008
C5—C7	1.524 (4)	O11—H111	0.838
C5—H51	1.027	O12—H121	0.820
O6—H61	0.843
F1—C2—C3	109.2 (3)	C5—C7—C9	110.4 (2)
F1—C2—H21	106.2	O8—C7—C9	112.3 (2)
C3—C2—H21	108.7	C5—C7—H71	110.3
F1—C2—H22	109.4	O8—C7—H71	109.4
C3—C2—H22	111.5	C9—C7—H71	106.9
H21—C2—H22	111.7	C7—O8—H81	116.5
C2—C3—O4	106.8 (2)	C7—C9—C10	110.5 (3)
C2—C3—C10	112.8 (3)	C7—C9—O12	112.0 (2)
O4—C3—C10	109.9 (2)	C10—C9—O12	111.0 (2)
C2—C3—H31	109.1	C7—C9—H91	108.1
O4—C3—H31	107.8	C10—C9—H91	108.0
C10—C3—H31	110.3	O12—C9—H91	107.0
C3—O4—C5	112.9 (2)	C9—C10—C3	108.4 (3)
O4—C5—O6	110.4 (3)	C9—C10—O11	109.2 (3)
O4—C5—C7	110.3 (2)	C3—C10—O11	110.9 (3)
O6—C5—C7	109.3 (2)	C9—C10—H101	109.5
O4—C5—H51	108.0	C3—C10—H101	108.1
O6—C5—H51	110.8	O11—C10—H101	110.7
C7—C5—H51	107.9	C10—O11—H111	104.6
C5—O6—H61	105.5	C9—O12—H121	112.3
C5—C7—O8	107.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H21···O12i	0.97	2.60	3.318 (4)	131
C5—H51···O11ii	1.03	2.59	3.320 (4)	128
O12—H121···O8iii	0.82	1.95	2.769 (4)	177
O11—H111···O12iv	0.84	1.96	2.781 (4)	168
O6—H61···O4ii	0.84	1.91	2.747 (4)	174
O8—H81···O6iii	0.82	1.93	2.739 (4)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O12—H121⋯O8i	0.82	1.95	2.769 (4)	177
O11—H111⋯O12ii	0.84	1.96	2.781 (4)	168
O6—H61⋯O4iii	0.84	1.91	2.747 (4)	174
O8—H81⋯O6i	0.82	1.93	2.739 (4)	169

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