1,2:5,6-Di-O-iso-propyl-idene-3-C-methyl-α-d-allo-furan-ose.

The title carbohydrate, C13H22O6, is a derivative of d-glycose, in which the furan-osidic and iso-propyl-idene rings are in twisted conformations. The mean plane of the furan-osidic ring makes a dihedral angle of 70.32 (18)° with the mean plane of the fused iso-propyl-idene ring. The methyl groups in the other iso-propyl-idene ring are disordered over two sets of sites, with an occupancy ratio of 0.74 (6):0.26 (6). In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds into chains with graph-set notation C(5) along [100]. Weak C-H⋯O interactions also occur.

Related literature

For background information on this class of compound, see: Bio et al. (2004 ▶); Canuto et al. (2007 ▶); Mane et al. (2008 ▶); Yoneda et al. (2011 ▶). For details of ring-puckering calculations, see: Cremer & Pople (1975 ▶). Graph-set notation for the description of hydrogen-bonding motifs is given by Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H22O6

M = 274.3

Triclinic,

a = 5.503 (4) Å

b = 8.113 (1) Å

c = 9.122 (2) Å

α = 99.65 (2)°

β = 103.69 (3)°

γ = 98.86 (2)°

V = 382.0 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.14 × 0.11 × 0.08 mm

Data collection

Nonius KappaCCD diffractometer

9589 measured reflections

2758 independent reflections

2107 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.130

S = 1.04

2758 reflections

181 parameters

8 restraints

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack x calculated using 872 quotients [(I +) − (I −)]/[(I +) + (I −)] (Parsons & Flack, 2004 ▶). There is insufficient information present to define handedness

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: DIRAX/LSQ (Duisenberg, 1992 ▶); data reduction: EVALCCD (Duisenberg et al., 2003 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2013 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813022447/pk2484sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022447/pk2484Isup2.hkl

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

C13H22O6	Z = 1
Mr = 274.3	F(000) = 148
Triclinic, P1	Dx = 1.192 Mg m−3
Hall symbol: P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.503 (4) Å	Cell parameters from 3284 reflections
b = 8.113 (1) Å	θ = 3.1–27.5°
c = 9.122 (2) Å	µ = 0.09 mm−1
α = 99.65 (2)°	T = 293 K
β = 103.69 (3)°	Prism, colourless
γ = 98.86 (2)°	0.14 × 0.11 × 0.08 mm
V = 382.0 (3) Å3

Nonius KappaCCD diffractometer	2107 reflections with I > 2σ(I)
Radiation source: Enraf–Nonius FR590	Rint = 0.043
Graphite monochromator	θmax = 25.7°, θmin = 3.1°
Detector resolution: 9 pixels mm-1	h = −6→6
CCD rotation images, thick slices scans	k = −9→9
9589 measured reflections	l = −11→11
2758 independent reflections

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.0707P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.046	(Δ/σ)max < 0.001
wR(F2) = 0.130	Δρmax = 0.21 e Å−3
S = 1.04	Δρmin = −0.24 e Å−3
2758 reflections	Extinction correction: SHELXL2013 (Sheldrick, 2013)
181 parameters	Extinction coefficient: 0.20 (3)
8 restraints	Absolute structure: Flack x calculated using 872 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004). There is insufficient information present to define handedness.
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: −0.2 (5)

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.2339 (6)	−0.0979 (4)	0.6028 (5)	0.0646 (10)
O2	−0.0659 (5)	0.0519 (3)	0.6425 (3)	0.0456 (8)
O3	−0.0994 (5)	0.3540 (4)	0.5720 (3)	0.0434 (7)
H3	−0.2119	0.2677	0.5383	0.065*
O4	0.3788 (5)	0.1260 (4)	0.4944 (3)	0.0446 (7)
O5	0.0585 (6)	0.3883 (5)	0.2656 (4)	0.0633 (10)
O6	0.2663 (8)	0.3148 (8)	0.0861 (5)	0.1016 (17)
C1	0.3517 (7)	0.0751 (5)	0.6312 (5)	0.0394 (9)
H1	0.5169	0.0992	0.7088	0.047*
C2	0.1689 (7)	0.1724 (5)	0.6883 (4)	0.0357 (9)
H2	0.2256	0.2197	0.7997	0.054*
C3	0.1409 (6)	0.3087 (5)	0.5930 (4)	0.0327 (9)
C4	0.1819 (7)	0.2156 (5)	0.4429 (5)	0.0397 (9)
H4	0.0255	0.1324	0.3853	0.048*
C5	0.2672 (8)	0.3188 (6)	0.3367 (5)	0.0486 (11)
H5	0.4124	0.411	0.3948	0.058*
C6	0.3295 (12)	0.2203 (10)	0.2017 (6)	0.0787 (18)
H6A	0.5092	0.2151	0.2255	0.094*
H6B	0.2282	0.1051	0.1701	0.094*
C7	0.0949 (10)	0.4150 (9)	0.1214 (6)	0.0727 (17)
C71A	0.222 (7)	0.598 (3)	0.144 (3)	0.149 (7)	0.74 (6)
H71A	0.0946	0.6662	0.1244	0.223*	0.74 (6)
H71C	0.3259	0.6077	0.0732	0.223*	0.74 (6)
H71B	0.3279	0.6382	0.2478	0.223*	0.74 (6)
C72A	−0.147 (3)	0.345 (4)	−0.0032 (17)	0.116 (6)	0.74 (6)
H72A	−0.1074	0.3085	−0.099	0.174*	0.74 (6)
H72B	−0.2456	0.4326	−0.0132	0.174*	0.74 (6)
H72C	−0.2427	0.2503	0.0222	0.174*	0.74 (6)
C71B	0.204 (18)	0.595 (8)	0.107 (11)	0.149 (7)	0.26 (6)
H71D	0.1085	0.6732	0.145	0.223*	0.26 (6)
H71E	0.1935	0.5954	0.0005	0.223*	0.26 (6)
H71F	0.3798	0.6279	0.1663	0.223*	0.26 (6)
C72B	−0.180 (6)	0.404 (11)	0.027 (6)	0.116 (6)	0.26 (6)
H72D	−0.1971	0.3568	−0.0794	0.174*	0.26 (6)
H72E	−0.2186	0.5155	0.0375	0.174*	0.26 (6)
H72F	−0.2952	0.3311	0.0647	0.174*	0.26 (6)
C8	−0.0148 (8)	−0.1149 (6)	0.6267 (6)	0.0517 (12)
C81	−0.2032 (11)	−0.2263 (8)	0.4845 (8)	0.0820 (17)
H81A	−0.1132	−0.2828	0.4198	0.123*
H81B	−0.3017	−0.1573	0.429	0.123*
H81C	−0.3152	−0.31	0.5137	0.123*
C82	−0.0177 (13)	−0.1798 (8)	0.7692 (8)	0.0823 (18)
H82A	0.1478	−0.2012	0.8139	0.123*
H82C	−0.1428	−0.2839	0.7441	0.123*
H82B	−0.0598	−0.0963	0.8418	0.123*
C9	0.3413 (8)	0.4681 (5)	0.6694 (5)	0.0454 (10)
H9C	0.3209	0.5524	0.6076	0.068*
H9B	0.5079	0.4417	0.6796	0.068*
H9A	0.3227	0.5117	0.7699	0.068*

	U11	U22	U33	U12	U13	U23
O1	0.0496 (18)	0.0411 (18)	0.120 (3)	0.0181 (14)	0.0450 (19)	0.0236 (18)
O2	0.0326 (14)	0.0361 (15)	0.079 (2)	0.0128 (12)	0.0242 (13)	0.0242 (14)
O3	0.0304 (14)	0.0420 (16)	0.0656 (19)	0.0149 (12)	0.0176 (13)	0.0193 (14)
O4	0.0368 (14)	0.0536 (17)	0.0531 (17)	0.0194 (13)	0.0218 (12)	0.0149 (14)
O5	0.066 (2)	0.102 (3)	0.0433 (17)	0.0418 (19)	0.0250 (15)	0.0373 (17)
O6	0.079 (3)	0.203 (5)	0.059 (2)	0.070 (3)	0.039 (2)	0.056 (3)
C1	0.031 (2)	0.043 (2)	0.052 (2)	0.0133 (17)	0.0156 (17)	0.0175 (19)
C2	0.0308 (19)	0.041 (2)	0.040 (2)	0.0105 (16)	0.0139 (16)	0.0117 (17)
C3	0.0270 (18)	0.037 (2)	0.038 (2)	0.0114 (16)	0.0119 (15)	0.0107 (17)
C4	0.0302 (19)	0.048 (2)	0.041 (2)	0.0087 (17)	0.0079 (16)	0.0101 (18)
C5	0.039 (2)	0.070 (3)	0.042 (2)	0.014 (2)	0.0138 (19)	0.021 (2)
C6	0.078 (4)	0.122 (5)	0.061 (3)	0.045 (4)	0.038 (3)	0.037 (3)
C7	0.055 (3)	0.132 (5)	0.045 (3)	0.030 (3)	0.019 (2)	0.037 (3)
C71A	0.239 (13)	0.140 (8)	0.076 (15)	0.001 (8)	0.059 (11)	0.059 (8)
C72A	0.057 (5)	0.26 (2)	0.048 (6)	0.069 (7)	0.023 (4)	0.033 (8)
C71B	0.239 (13)	0.140 (8)	0.076 (15)	0.001 (8)	0.059 (11)	0.059 (8)
C72B	0.057 (5)	0.26 (2)	0.048 (6)	0.069 (7)	0.023 (4)	0.033 (8)
C8	0.043 (2)	0.041 (2)	0.083 (3)	0.017 (2)	0.031 (2)	0.021 (2)
C81	0.066 (4)	0.056 (3)	0.115 (5)	0.002 (3)	0.025 (3)	0.005 (3)
C82	0.097 (4)	0.073 (4)	0.112 (5)	0.041 (3)	0.055 (4)	0.056 (4)
C9	0.043 (2)	0.038 (2)	0.056 (2)	0.0101 (18)	0.0146 (18)	0.0080 (18)

O1—C1	1.405 (5)	C7—C71B	1.53 (3)
O1—C8	1.426 (5)	C7—C72B	1.53 (2)
O2—C8	1.415 (5)	C71A—H71A	0.96
O2—C2	1.421 (5)	C71A—H71C	0.96
O3—C3	1.405 (4)	C71A—H71B	0.96
O3—H3	0.82	C72A—H72A	0.96
O4—C1	1.412 (5)	C72A—H72B	0.96
O4—C4	1.428 (5)	C72A—H72C	0.96
O5—C7	1.422 (6)	C71B—H71D	0.96
O5—C5	1.423 (5)	C71B—H71E	0.96
O6—C7	1.395 (8)	C71B—H71F	0.96
O6—C6	1.415 (8)	C72B—H72D	0.96
C1—C2	1.504 (5)	C72B—H72E	0.96
C1—H1	0.98	C72B—H72F	0.96
C2—C3	1.521 (5)	C8—C82	1.485 (8)
C2—H2	0.98	C8—C81	1.503 (8)
C3—C9	1.506 (6)	C81—H81A	0.96
C3—C4	1.532 (6)	C81—H81B	0.96
C4—C5	1.493 (5)	C81—H81C	0.96
C4—H4	0.98	C82—H82A	0.96
C5—C6	1.492 (7)	C82—H82C	0.96
C5—H5	0.98	C82—H82B	0.96
C6—H6A	0.97	C9—H9C	0.96
C6—H6B	0.97	C9—H9B	0.96
C7—C72A	1.489 (12)	C9—H9A	0.96
C7—C71A	1.502 (16)
C1—O1—C8	110.7 (3)	O5—C7—C72B	102 (2)
C8—O2—C2	109.1 (3)	C71B—C7—C72B	97 (2)
C3—O3—H3	109.5	C7—C71A—H71A	109.5
C1—O4—C4	109.0 (3)	C7—C71A—H71C	109.5
C7—O5—C5	106.9 (4)	H71A—C71A—H71C	109.5
C7—O6—C6	109.5 (4)	C7—C71A—H71B	109.5
O1—C1—O4	111.8 (4)	H71A—C71A—H71B	109.5
O1—C1—C2	105.2 (3)	H71C—C71A—H71B	109.5
O4—C1—C2	106.8 (3)	C7—C72A—H72A	109.5
O1—C1—H1	110.9	C7—C72A—H72B	109.5
O4—C1—H1	110.9	H72A—C72A—H72B	109.5
C2—C1—H1	110.9	C7—C72A—H72C	109.5
O2—C2—C1	104.0 (3)	H72A—C72A—H72C	109.5
O2—C2—C3	108.0 (3)	H72B—C72A—H72C	109.5
C1—C2—C3	105.1 (3)	C7—C71B—H71D	109.5
O2—C2—H2	113	C7—C71B—H71E	109.5
C1—C2—H2	113	H71D—C71B—H71E	109.5
C3—C2—H2	113	C7—C71B—H71F	109.5
O3—C3—C9	107.8 (3)	H71D—C71B—H71F	109.5
O3—C3—C2	112.6 (3)	H71E—C71B—H71F	109.5
C9—C3—C2	110.7 (3)	C7—C72B—H72D	109.5
O3—C3—C4	112.9 (3)	C7—C72B—H72E	109.5
C9—C3—C4	112.8 (3)	H72D—C72B—H72E	109.5
C2—C3—C4	100.0 (3)	C7—C72B—H72F	109.5
O4—C4—C5	107.2 (3)	H72D—C72B—H72F	109.5
O4—C4—C3	103.8 (3)	H72E—C72B—H72F	109.5
C5—C4—C3	118.7 (3)	O2—C8—O1	105.1 (3)
O4—C4—H4	108.9	O2—C8—C82	110.5 (4)
C5—C4—H4	108.9	O1—C8—C82	110.4 (4)
C3—C4—H4	108.9	O2—C8—C81	108.5 (4)
O5—C5—C6	102.8 (4)	O1—C8—C81	108.6 (4)
O5—C5—C4	108.1 (3)	C82—C8—C81	113.3 (5)
C6—C5—C4	115.4 (4)	C8—C81—H81A	109.5
O5—C5—H5	110.1	C8—C81—H81B	109.5
C6—C5—H5	110.1	H81A—C81—H81B	109.5
C4—C5—H5	110.1	C8—C81—H81C	109.5
O6—C6—C5	103.3 (5)	H81A—C81—H81C	109.5
O6—C6—H6A	111.1	H81B—C81—H81C	109.5
C5—C6—H6A	111.1	C8—C82—H82A	109.5
O6—C6—H6B	111.1	C8—C82—H82C	109.5
C5—C6—H6B	111.1	H82A—C82—H82C	109.5
H6A—C6—H6B	109.1	C8—C82—H82B	109.5
O6—C7—O5	106.7 (4)	H82A—C82—H82B	109.5
O6—C7—C72A	105.2 (14)	H82C—C82—H82B	109.5
O5—C7—C72A	110.0 (8)	C3—C9—H9C	109.5
O6—C7—C71A	107.4 (16)	C3—C9—H9B	109.5
O5—C7—C71A	107.9 (12)	H9C—C9—H9B	109.5
C72A—C7—C71A	118.9 (19)	C3—C9—H9A	109.5
O6—C7—C71B	106 (5)	H9C—C9—H9A	109.5
O5—C7—C71B	119 (4)	H9B—C9—H9A	109.5
O6—C7—C72B	127 (3)
C8—O1—C1—O4	−111.3 (4)	C7—O5—C5—C4	−153.6 (4)
C8—O1—C1—C2	4.3 (5)	O4—C4—C5—O5	171.2 (4)
C4—O4—C1—O1	100.8 (3)	C3—C4—C5—O5	−71.9 (4)
C4—O4—C1—C2	−13.8 (4)	O4—C4—C5—C6	56.8 (5)
C8—O2—C2—C1	24.8 (4)	C3—C4—C5—C6	173.7 (4)
C8—O2—C2—C3	136.1 (3)	C7—O6—C6—C5	−21.4 (7)
O1—C1—C2—O2	−17.4 (4)	O5—C5—C6—O6	31.7 (6)
O4—C1—C2—O2	101.6 (3)	C4—C5—C6—O6	149.1 (4)
O1—C1—C2—C3	−130.8 (3)	C6—O6—C7—O5	2.5 (7)
O4—C1—C2—C3	−11.8 (4)	C6—O6—C7—C72A	−114.4 (10)
O2—C2—C3—O3	39.9 (4)	C6—O6—C7—C71A	118.0 (13)
C1—C2—C3—O3	150.4 (3)	C6—O6—C7—C71B	130 (3)
O2—C2—C3—C9	160.6 (3)	C6—O6—C7—C72B	−117 (3)
C1—C2—C3—C9	−88.8 (4)	C5—O5—C7—O6	18.7 (6)
O2—C2—C3—C4	−80.2 (3)	C5—O5—C7—C72A	132.4 (15)
C1—C2—C3—C4	30.3 (4)	C5—O5—C7—C71A	−96.4 (17)
C1—O4—C4—C5	160.1 (3)	C5—O5—C7—C71B	−101 (5)
C1—O4—C4—C3	33.7 (4)	C5—O5—C7—C72B	154 (3)
O3—C3—C4—O4	−158.5 (3)	C2—O2—C8—O1	−22.4 (5)
C9—C3—C4—O4	78.9 (4)	C2—O2—C8—C82	96.6 (5)
C2—C3—C4—O4	−38.6 (3)	C2—O2—C8—C81	−138.5 (4)
O3—C3—C4—C5	82.7 (4)	C1—O1—C8—O2	10.6 (5)
C9—C3—C4—C5	−39.8 (4)	C1—O1—C8—C82	−108.5 (5)
C2—C3—C4—C5	−157.4 (3)	C1—O1—C8—C81	126.6 (4)
C7—O5—C5—C6	−31.1 (6)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4i	0.82	2.28	3.022 (4)	152
C1—H1···O2ii	0.98	2.58	3.218 (5)	123
C2—H2···O6iii	0.98	2.54	3.504 (5)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4i	0.82	2.28	3.022 (4)	152
C1—H1⋯O2ii	0.98	2.58	3.218 (5)	123
C2—H2⋯O6iii	0.98	2.54	3.504 (5)	167

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