6-De-oxy-3,4-O-isopropyl-idene-2-C-methyl-l-galactono-1,5-lactone.

X-ray crystallography unequivocally confirmed the stereochemistry of the 2-C-methyl group in the title mol-ecule, C(10)H(16)O(5), in which the 1,5-lactone ring exists in a boat conformation. The absolute stereochemistry was determined by the use of d-ribose in the synthesis. The crystal exists as O-H⋯O hydrogen bonded chains of mol-ecules running parallel to the a axis with each mol-ecule acting as a donor and acceptor for one hydrogen bond.

Related literature

For branched imino­sugars, see: Håkansson et al. (2007 ▶, 2008 ▶); Asano et al. (2000 ▶); da Cruz et al. (2011 ▶); Best et al. (2010 ▶) and for branched sugars, see: Booth et al. (2008 ▶, 2009 ▶); da Cruz et al. (2008 ▶); Hotchkiss et al. (2006 ▶, 2007 ▶); Jenkinson et al. (2007 ▶); Jones et al. (2007 ▶, 2008 ▶); Rao et al. (2008 ▶). For conformations of related 1,5-lactones, see: Baird et al. (1987 ▶); Booth et al. (2007a ▶,b ▶); Bruce et al. (1990 ▶); Punzo et al. (2005 ▶, 2006 ▶); Dai et al. (2010 ▶).

Experimental

Crystal data

C10H16O5

M = 216.23

Orthorhombic,

a = 6.1132 (2) Å

b = 12.2963 (4) Å

c = 14.6367 (5) Å

V = 1100.24 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 150 K

0.20 × 0.20 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.95, T max = 1.00

8628 measured reflections

1454 independent reflections

1131 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 0.89

1454 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.29 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 datablock(s) global, I. DOI: 10.1107/S1600536811034957/lh5321sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034957/lh5321Isup2.hkl

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

C10H16O5	F(000) = 464
Mr = 216.23	Dx = 1.305 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1433 reflections
a = 6.1132 (2) Å	θ = 5–27°
b = 12.2963 (4) Å	µ = 0.11 mm−1
c = 14.6367 (5) Å	T = 150 K
V = 1100.24 (6) Å3	Plate, colourless
Z = 4	0.20 × 0.20 × 0.04 mm

Nonius KappaCCD diffractometer	1131 reflections with I > 2σ(I)
graphite	Rint = 0.067
ω scans	θmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.95, Tmax = 1.00	k = −15→15
8628 measured reflections	l = −18→19
1454 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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.090	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.06P)2 + 0.14P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.89	(Δ/σ)max = 0.000259
1454 reflections	Δρmax = 0.40 e Å−3
136 parameters	Δρmin = −0.29 e Å−3
0 restraints

	x	y	z	Uiso*/Ueq
O1	−0.0165 (3)	0.80556 (12)	0.89995 (10)	0.0290
C2	0.1164 (4)	0.75275 (16)	0.85712 (12)	0.0226
O3	0.0426 (3)	0.68163 (11)	0.79561 (10)	0.0287
C4	0.1986 (4)	0.60986 (16)	0.74843 (14)	0.0289
C5	0.3861 (4)	0.67578 (16)	0.71001 (14)	0.0271
O6	0.3108 (3)	0.73556 (12)	0.63264 (9)	0.0355
C7	0.4068 (4)	0.84132 (17)	0.63637 (13)	0.0292
O8	0.4222 (3)	0.86365 (10)	0.73198 (9)	0.0261
C9	0.4744 (4)	0.76299 (15)	0.77626 (13)	0.0240
C10	0.3643 (4)	0.76166 (16)	0.86972 (13)	0.0221
O11	0.4337 (3)	0.66259 (11)	0.91228 (10)	0.0301
C12	0.4222 (4)	0.86099 (16)	0.92581 (13)	0.0277
C13	0.2506 (5)	0.92177 (19)	0.59465 (16)	0.0401
C14	0.6306 (5)	0.8415 (2)	0.59246 (16)	0.0422
C15	0.0664 (5)	0.55020 (19)	0.67809 (16)	0.0402
H41	0.2554	0.5572	0.7948	0.0338*
H51	0.5068	0.6260	0.6926	0.0337*
H91	0.6348	0.7543	0.7832	0.0290*
H121	0.5803	0.8627	0.9363	0.0432*
H122	0.3490	0.8570	0.9864	0.0426*
H123	0.3742	0.9272	0.8933	0.0431*
H131	0.3082	0.9961	0.6014	0.0583*
H132	0.2349	0.9048	0.5289	0.0582*
H133	0.1099	0.9171	0.6262	0.0586*
H141	0.6868	0.9161	0.5934	0.0627*
H142	0.7280	0.7929	0.6268	0.0622*
H143	0.6166	0.8179	0.5275	0.0623*
H153	0.1616	0.4999	0.6465	0.0610*
H152	−0.0508	0.5092	0.7077	0.0613*
H151	0.0062	0.6022	0.6340	0.0612*
H111	0.4361	0.6716	0.9708	0.0460*

	U11	U22	U33	U12	U13	U23
O1	0.0284 (9)	0.0329 (8)	0.0257 (7)	0.0061 (7)	0.0025 (7)	0.0035 (7)
C2	0.0264 (11)	0.0224 (10)	0.0191 (8)	0.0006 (10)	0.0006 (9)	0.0049 (9)
O3	0.0263 (8)	0.0302 (8)	0.0295 (8)	−0.0029 (7)	0.0011 (6)	−0.0051 (6)
C4	0.0344 (13)	0.0224 (10)	0.0299 (11)	0.0027 (9)	0.0008 (10)	−0.0023 (9)
C5	0.0315 (12)	0.0276 (10)	0.0222 (9)	0.0034 (10)	0.0012 (10)	−0.0035 (9)
O6	0.0500 (11)	0.0332 (8)	0.0234 (7)	−0.0145 (8)	−0.0068 (7)	0.0026 (7)
C7	0.0354 (13)	0.0305 (12)	0.0216 (10)	−0.0092 (11)	−0.0011 (10)	−0.0005 (9)
O8	0.0326 (8)	0.0250 (7)	0.0208 (7)	−0.0002 (7)	0.0006 (6)	0.0007 (6)
C9	0.0220 (11)	0.0253 (10)	0.0248 (9)	0.0032 (9)	0.0000 (9)	−0.0009 (9)
C10	0.0246 (11)	0.0198 (10)	0.0220 (9)	0.0042 (9)	−0.0017 (9)	0.0009 (8)
O11	0.0405 (9)	0.0267 (7)	0.0233 (7)	0.0089 (7)	−0.0047 (7)	0.0023 (6)
C12	0.0300 (12)	0.0288 (11)	0.0243 (10)	0.0005 (10)	−0.0028 (10)	−0.0022 (9)
C13	0.0453 (16)	0.0394 (13)	0.0355 (12)	−0.0026 (13)	−0.0080 (13)	0.0110 (12)
C14	0.0470 (16)	0.0480 (14)	0.0316 (11)	−0.0057 (14)	0.0137 (12)	−0.0004 (12)
C15	0.0509 (17)	0.0330 (12)	0.0368 (12)	−0.0104 (12)	−0.0011 (13)	−0.0088 (10)

O1—C2	1.214 (2)	C9—H91	0.992
C2—O3	1.334 (2)	C10—O11	1.433 (2)
C2—C10	1.530 (3)	C10—C12	1.514 (3)
O3—C4	1.472 (3)	O11—H111	0.864
C4—C5	1.512 (3)	C12—H121	0.979
C4—C15	1.501 (3)	C12—H122	0.995
C4—H41	1.000	C12—H123	0.987
C5—O6	1.426 (2)	C13—H131	0.985
C5—C9	1.543 (3)	C13—H132	0.989
C5—H51	0.992	C13—H133	0.978
O6—C7	1.428 (3)	C14—H141	0.979
C7—O8	1.429 (2)	C14—H142	0.982
C7—C13	1.505 (3)	C14—H143	0.997
C7—C14	1.512 (3)	C15—H153	0.967
O8—C9	1.433 (2)	C15—H152	0.977
C9—C10	1.525 (3)	C15—H151	0.980
O1—C2—O3	118.2 (2)	C2—C10—O11	106.55 (17)
O1—C2—C10	124.18 (18)	C9—C10—O11	105.58 (16)
O3—C2—C10	117.60 (18)	C2—C10—C12	110.78 (18)
C2—O3—C4	119.38 (17)	C9—C10—C12	112.01 (17)
O3—C4—C5	110.13 (15)	O11—C10—C12	112.40 (15)
O3—C4—C15	105.41 (19)	C10—O11—H111	109.1
C5—C4—C15	114.54 (18)	C10—C12—H121	109.5
O3—C4—H41	107.1	C10—C12—H122	109.8
C5—C4—H41	109.7	H121—C12—H122	107.8
C15—C4—H41	109.6	C10—C12—H123	109.5
C4—C5—O6	109.09 (18)	H121—C12—H123	110.5
C4—C5—C9	113.83 (17)	H122—C12—H123	109.7
O6—C5—C9	104.69 (15)	C7—C13—H131	110.0
C4—C5—H51	109.2	C7—C13—H132	108.5
O6—C5—H51	110.7	H131—C13—H132	109.2
C9—C5—H51	109.3	C7—C13—H133	109.2
C5—O6—C7	107.85 (16)	H131—C13—H133	108.7
O6—C7—O8	103.85 (15)	H132—C13—H133	111.2
O6—C7—C13	108.81 (18)	C7—C14—H141	108.2
O8—C7—C13	108.23 (18)	C7—C14—H142	109.3
O6—C7—C14	110.92 (18)	H141—C14—H142	110.5
O8—C7—C14	110.89 (19)	C7—C14—H143	109.1
C13—C7—C14	113.65 (18)	H141—C14—H143	108.4
C7—O8—C9	106.95 (14)	H142—C14—H143	111.3
C5—C9—O8	103.77 (15)	C4—C15—H153	108.4
C5—C9—C10	113.70 (17)	C4—C15—H152	110.1
O8—C9—C10	108.47 (15)	H153—C15—H152	108.9
C5—C9—H91	109.6	C4—C15—H151	109.6
O8—C9—H91	111.1	H153—C15—H151	109.1
C10—C9—H91	110.1	H152—C15—H151	110.7
C2—C10—C9	109.25 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H131···O11i	0.99	2.59	3.536 (3)	161
O11—H111···O1ii	0.86	1.93	2.793 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O11—H111⋯O1i	0.86	1.93	2.793 (3)	172

Symmetry code: (i) .