3,4-O-Isopropyl-idene-2-C-methyl-d-galactonolactone.

X-ray crystallography unequivocally confirmed the stereochemistry of the 2-C-methyl group in the title mol-ecule, C(10)H(16)O(6), in which the 1,5-lactone ring exists in a boat conformation. The use of d-galactose in the synthesis determined the absolute stereochemistry. The crystal exists as O-H⋯O hydrogen-bonded layers in the ab plane, with each mol-ecule acting as a donor and acceptor for two hydrogen bonds.

Related literature

For related literature on 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 the 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 ▶).

Experimental

Crystal data

C10H16O6

M = 232.23

Monoclinic,

a = 6.0553 (2) Å

b = 11.3612 (4) Å

c = 8.2946 (3) Å

β = 105.0854 (14)°

V = 550.97 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 150 K

0.50 × 0.40 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.91, T max = 0.99

5558 measured reflections

1314 independent reflections

1229 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.068

S = 0.98

1313 reflections

145 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 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/S1600536810001613/lh2976sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001613/lh2976Isup2.hkl

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

C10H16O6	F(000) = 248
Mr = 232.23	Dx = 1.400 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1236 reflections
a = 6.0553 (2) Å	θ = 5–27°
b = 11.3612 (4) Å	µ = 0.12 mm−1
c = 8.2946 (3) Å	T = 150 K
β = 105.0854 (14)°	Plate, colourless
V = 550.97 (3) Å3	0.50 × 0.40 × 0.10 mm
Z = 2

Nonius KappaCCD diffractometer	1229 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 27.5°, θmin = 5.2°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −7→7
Tmin = 0.91, Tmax = 0.99	k = −14→14
5558 measured reflections	l = −10→10
1314 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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.068	Method = Modified Sheldrick w = 1/[σ2(F2) + (0.03P)2 + 0.19P], where P = [max(Fo2,0) + 2Fc2]/3
S = 0.98	(Δ/σ)max = 0.0002
1313 reflections	Δρmax = 0.22 e Å−3
145 parameters	Δρmin = −0.18 e Å−3
1 restraint

	x	y	z	Uiso*/Ueq
O1	0.1833 (2)	0.44365 (15)	0.34373 (17)	0.0239
C2	0.2057 (3)	0.50024 (18)	0.1948 (2)	0.0213
C3	0.3440 (3)	0.61260 (18)	0.2310 (2)	0.0182
O4	0.5789 (2)	0.57762 (14)	0.31079 (16)	0.0207
C5	0.7424 (3)	0.65953 (18)	0.3392 (2)	0.0190
O6	0.9366 (2)	0.63080 (16)	0.41067 (17)	0.0258
C7	0.6739 (3)	0.78590 (18)	0.2822 (2)	0.0185
O8	0.5348 (2)	0.82928 (15)	0.38453 (17)	0.0224
C9	0.8833 (3)	0.86206 (19)	0.2930 (3)	0.0236
C10	0.5160 (3)	0.78355 (18)	0.1047 (2)	0.0193
C11	0.3342 (3)	0.68457 (18)	0.0755 (2)	0.0190
O12	0.3897 (2)	0.61111 (14)	−0.04874 (16)	0.0232
C13	0.5062 (3)	0.6857 (2)	−0.1390 (2)	0.0225
O14	0.6490 (2)	0.75665 (14)	−0.00941 (15)	0.0220
C15	0.3374 (4)	0.7604 (2)	−0.2640 (2)	0.0300
C16	0.6590 (4)	0.6125 (2)	−0.2164 (3)	0.0307
H21	0.0514	0.5221	0.1280	0.0253*
H22	0.2831	0.4457	0.1327	0.0254*
H31	0.2876	0.6635	0.3096	0.0192*
H91	0.8339	0.9420	0.2601	0.0333*
H93	0.9791	0.8665	0.4043	0.0339*
H92	0.9711	0.8323	0.2182	0.0336*
H101	0.4445	0.8626	0.0784	0.0218*
H111	0.1751	0.7172	0.0354	0.0205*
H152	0.4259	0.8092	−0.3237	0.0421*
H151	0.2464	0.8116	−0.2113	0.0424*
H153	0.2412	0.7087	−0.3440	0.0423*
H161	0.7445	0.6676	−0.2693	0.0459*
H163	0.7596	0.5680	−0.1332	0.0464*
H162	0.5654	0.5645	−0.3003	0.0462*
H81	0.6206	0.8478	0.4729	0.0319*
H11	0.0902	0.4790	0.3908	0.0358*

	U11	U22	U33	U12	U13	U23
O1	0.0268 (7)	0.0221 (7)	0.0249 (7)	0.0017 (6)	0.0104 (6)	0.0072 (6)
C2	0.0241 (9)	0.0199 (9)	0.0194 (9)	−0.0019 (8)	0.0050 (7)	0.0033 (7)
C3	0.0163 (8)	0.0196 (9)	0.0185 (8)	0.0022 (7)	0.0043 (7)	0.0024 (7)
O4	0.0184 (6)	0.0193 (6)	0.0232 (7)	0.0023 (5)	0.0035 (5)	0.0035 (5)
C5	0.0203 (9)	0.0226 (10)	0.0148 (8)	0.0012 (7)	0.0063 (7)	−0.0010 (7)
O6	0.0196 (6)	0.0291 (7)	0.0272 (7)	0.0038 (6)	0.0031 (5)	0.0015 (6)
C7	0.0194 (8)	0.0196 (9)	0.0170 (8)	0.0014 (7)	0.0057 (7)	−0.0032 (7)
O8	0.0222 (6)	0.0250 (7)	0.0207 (6)	0.0006 (6)	0.0068 (5)	−0.0069 (5)
C9	0.0227 (9)	0.0232 (10)	0.0249 (10)	−0.0026 (8)	0.0063 (8)	−0.0035 (8)
C10	0.0235 (9)	0.0176 (9)	0.0171 (8)	0.0001 (8)	0.0058 (7)	0.0002 (7)
C11	0.0214 (9)	0.0181 (9)	0.0176 (8)	−0.0007 (7)	0.0051 (7)	−0.0003 (7)
O12	0.0324 (7)	0.0206 (7)	0.0185 (6)	−0.0065 (6)	0.0100 (6)	−0.0021 (5)
C13	0.0308 (10)	0.0228 (9)	0.0144 (8)	−0.0088 (8)	0.0070 (7)	−0.0017 (7)
O14	0.0252 (7)	0.0249 (7)	0.0173 (6)	−0.0066 (6)	0.0082 (5)	−0.0036 (5)
C15	0.0354 (11)	0.0336 (12)	0.0187 (9)	−0.0047 (9)	0.0028 (8)	0.0035 (8)
C16	0.0400 (11)	0.0315 (11)	0.0239 (10)	−0.0037 (9)	0.0140 (9)	−0.0059 (9)

O1—C2	1.430 (2)	C9—H92	0.976
O1—H11	0.864	C10—C11	1.548 (3)
C2—C3	1.513 (3)	C10—O14	1.426 (2)
C2—H21	0.985	C10—H101	0.996
C2—H22	0.997	C11—O12	1.432 (2)
C3—O4	1.459 (2)	C11—H111	1.005
C3—C11	1.516 (3)	O12—C13	1.432 (2)
C3—H31	0.995	C13—O14	1.439 (2)
O4—C5	1.334 (2)	C13—C15	1.513 (3)
C5—O6	1.216 (2)	C13—C16	1.506 (3)
C5—C7	1.534 (3)	C15—H152	0.990
C7—O8	1.430 (2)	C15—H151	0.979
C7—C9	1.519 (3)	C15—H153	0.961
C7—C10	1.533 (3)	C16—H161	0.985
O8—H81	0.808	C16—H163	0.940
C9—H91	0.973	C16—H162	0.947
C9—H93	0.956
C2—O1—H11	113.6	C7—C10—O14	108.81 (14)
O1—C2—C3	112.29 (15)	C11—C10—O14	103.99 (14)
O1—C2—H21	108.0	C7—C10—H101	108.8
C3—C2—H21	107.1	C11—C10—H101	111.7
O1—C2—H22	109.3	O14—C10—H101	109.7
C3—C2—H22	108.4	C10—C11—C3	112.96 (15)
H21—C2—H22	111.8	C10—C11—O12	104.22 (14)
C2—C3—O4	106.51 (15)	C3—C11—O12	109.48 (15)
C2—C3—C11	112.89 (15)	C10—C11—H111	111.4
O4—C3—C11	110.51 (14)	C3—C11—H111	107.6
C2—C3—H31	110.7	O12—C11—H111	111.2
O4—C3—H31	108.7	C11—O12—C13	105.74 (14)
C11—C3—H31	107.5	O12—C13—O14	102.88 (13)
C3—O4—C5	118.76 (15)	O12—C13—C15	110.69 (16)
O4—C5—O6	118.55 (17)	O14—C13—C15	111.39 (17)
O4—C5—C7	118.00 (15)	O12—C13—C16	109.71 (17)
O6—C5—C7	123.44 (17)	O14—C13—C16	108.15 (17)
C5—C7—O8	107.07 (14)	C15—C13—C16	113.47 (16)
C5—C7—C9	111.12 (15)	C13—O14—C10	106.42 (14)
O8—C7—C9	112.38 (15)	C13—C15—H152	107.5
C5—C7—C10	109.30 (14)	C13—C15—H151	112.7
O8—C7—C10	105.05 (14)	H152—C15—H151	109.4
C9—C7—C10	111.64 (15)	C13—C15—H153	108.1
C7—O8—H81	106.8	H152—C15—H153	107.9
C7—C9—H91	108.9	H151—C15—H153	111.2
C7—C9—H93	112.0	C13—C16—H161	106.9
H91—C9—H93	106.6	C13—C16—H163	109.6
C7—C9—H92	110.5	H161—C16—H163	110.7
H91—C9—H92	108.9	C13—C16—H162	108.3
H93—C9—H92	109.8	H161—C16—H162	108.8
C7—C10—C11	113.78 (14)	H163—C16—H162	112.3

D—H···A	D—H	H···A	D···A	D—H···A
C2—H22···O14i	1.00	2.46	3.391 (3)	155
C3—H31···O6ii	1.00	2.51	3.204 (3)	127
C15—H153···O6iii	0.96	2.52	3.454 (3)	163
O8—H81···O1iv	0.81	1.99	2.771 (3)	162
O1—H11···O6ii	0.86	1.99	2.737 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H81⋯O1i	0.81	1.99	2.771 (3)	162
O1—H11⋯O6ii	0.86	1.99	2.737 (3)	145

Symmetry codes: (i) ; (ii) .