Methyl 6-de-oxy-6-iodo-α-d-galactoside.

In the crystal of the title compound, C(7)H(13)IO(5), the molecules are linked by O-H⋯O hydrogen bonds, which build linkages around one screw axis of the cell. These C(5) and C(6) packing motifs expand to R(2) (2)(10) and C(2) (2)(11) motifs and are similar to those found for closely related compounds. The galactoside ring has a (1)C(4) chair conformation.

Related literature

For the synthetic details, see Dangerfield et al. (2009 ▶); Stocker et al.(2010 ▶). For related structures, see Sikorski et al. (2009 ▶), Robertson & Sheldrick (1965 ▶). For ring conformations see: Cremer & Pople (1975 ▶) and for hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H13IO5

M = 304.08

Orthorhombic,

a = 5.7745 (2) Å

b = 7.9055 (3) Å

c = 22.1835 (7) Å

V = 1012.68 (6) Å3

Z = 4

Mo Kα radiation

μ = 3.15 mm−1

T = 111 K

0.51 × 0.30 × 0.02 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.523, T max = 0.747

30359 measured reflections

4062 independent reflections

3930 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.050

S = 1.06

4062 reflections

122 parameters

H-atom parameters constrained

Δρmax = 1.45 e Å−3

Δρmin = −0.78 e Å−3

Absolute structure: Flack (1983 ▶), 1653 Friedel pairs

Flack parameter: 0.002 (13)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT and SADABS (Bruker, 2005 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶), Mercury (Macrae et al., 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810022786/lh5062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022786/lh5062Isup2.hkl

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

C7H13IO5	F(000) = 592
Mr = 304.08	Dx = 1.994 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9870 reflections
a = 5.7745 (2) Å	θ = 2.6–34.2°
b = 7.9055 (3) Å	µ = 3.15 mm−1
c = 22.1835 (7) Å	T = 111 K
V = 1012.68 (6) Å3	Plate, colourless
Z = 4	0.51 × 0.30 × 0.02 mm

Bruker APEXII CCD diffractometer	4062 independent reflections
Radiation source: fine-focus sealed tube	3930 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 8.333 pixels mm-1	θmax = 35.0°, θmin = 2.7°
φ and ω scans	h = −8→9
Absorption correction: multi-scan (Blessing, 1995)	k = −12→11
Tmin = 0.523, Tmax = 0.747	l = −33→33
30359 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H-atom parameters constrained
wR(F2) = 0.050	w = 1/[σ2(Fo2) + (0.0236P)2 + 0.4353P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
4062 reflections	Δρmax = 1.45 e Å−3
122 parameters	Δρmin = −0.78 e Å−3
0 restraints	Absolute structure: Flack (1983), 1653 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.002 (13)

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
I1	0.40872 (2)	0.478714 (16)	0.504464 (5)	0.02898 (4)
O1	0.5838 (2)	0.12645 (13)	0.34021 (5)	0.01598 (19)
O2	0.67433 (18)	0.21293 (14)	0.22048 (5)	0.01352 (19)
H2O	0.7581	0.1333	0.2328	0.020*
O3	1.03501 (17)	0.45621 (14)	0.24533 (5)	0.01504 (19)
H3O	1.0745	0.3781	0.2218	0.023*
O4	0.77547 (18)	0.67940 (13)	0.31887 (6)	0.01447 (19)
H4O	0.6341	0.6700	0.3106	0.022*
O5	0.47929 (18)	0.40652 (14)	0.36225 (5)	0.01431 (19)
C1	0.4969 (2)	0.27912 (17)	0.31726 (7)	0.0122 (2)
H1	0.3391	0.2579	0.3003	0.018*
C2	0.6547 (2)	0.33786 (17)	0.26630 (7)	0.0107 (2)
H2	0.5829	0.4406	0.2478	0.016*
C3	0.8900 (2)	0.38930 (17)	0.29162 (7)	0.0118 (2)
H3	0.9664	0.2872	0.3093	0.018*
C4	0.8602 (2)	0.52225 (19)	0.34128 (6)	0.0131 (2)
H4	1.0147	0.5426	0.3603	0.020*
C5	0.6977 (2)	0.44721 (18)	0.38928 (7)	0.0145 (2)
H5	0.7687	0.3423	0.4064	0.022*
C6	0.6533 (3)	0.5722 (2)	0.43929 (8)	0.0239 (3)
H6A	0.5936	0.6788	0.4217	0.036*
H6B	0.8013	0.5980	0.4599	0.036*
C7	0.4228 (3)	0.0461 (2)	0.38037 (8)	0.0239 (3)
H7A	0.4069	0.1141	0.4171	0.036*
H7B	0.4798	−0.0668	0.3909	0.036*
H7C	0.2717	0.0362	0.3606	0.036*

	U11	U22	U33	U12	U13	U23
I1	0.03654 (6)	0.02910 (6)	0.02130 (5)	0.00409 (4)	0.01094 (4)	0.00063 (4)
O1	0.0168 (4)	0.0098 (4)	0.0213 (5)	−0.0006 (4)	0.0006 (4)	0.0029 (3)
O2	0.0113 (4)	0.0111 (4)	0.0182 (5)	0.0009 (3)	−0.0005 (4)	−0.0027 (4)
O3	0.0118 (4)	0.0134 (4)	0.0199 (5)	−0.0024 (3)	0.0043 (3)	−0.0023 (4)
O4	0.0124 (4)	0.0092 (4)	0.0218 (5)	−0.0001 (3)	−0.0002 (4)	0.0013 (4)
O5	0.0124 (4)	0.0133 (5)	0.0172 (5)	0.0013 (3)	0.0022 (4)	−0.0012 (4)
C1	0.0096 (5)	0.0103 (5)	0.0168 (6)	0.0000 (4)	0.0004 (4)	0.0003 (5)
C2	0.0079 (4)	0.0101 (5)	0.0141 (6)	−0.0001 (4)	−0.0002 (4)	−0.0007 (4)
C3	0.0081 (5)	0.0109 (5)	0.0163 (6)	−0.0009 (4)	0.0005 (4)	−0.0001 (4)
C4	0.0119 (5)	0.0107 (5)	0.0167 (6)	−0.0003 (4)	−0.0016 (4)	0.0008 (5)
C5	0.0165 (6)	0.0123 (6)	0.0149 (6)	−0.0004 (5)	−0.0009 (5)	0.0002 (5)
C6	0.0341 (8)	0.0179 (7)	0.0197 (8)	−0.0040 (6)	0.0073 (6)	−0.0047 (6)
C7	0.0311 (8)	0.0190 (7)	0.0218 (7)	−0.0062 (7)	0.0037 (6)	0.0055 (5)

I1—C6	2.1521 (18)	C2—C3	1.5252 (18)
O1—C1	1.4027 (17)	C2—H2	1.0000
O1—C7	1.436 (2)	C3—C4	1.532 (2)
O2—C2	1.4219 (18)	C3—H3	1.0000
O2—H2O	0.8400	C4—C5	1.538 (2)
O3—C3	1.4268 (17)	C4—H4	1.0000
O3—H3O	0.8400	C5—C6	1.508 (2)
O4—C4	1.4248 (17)	C5—H5	1.0000
O4—H4O	0.8400	C6—H6A	0.9900
O5—C1	1.4217 (18)	C6—H6B	0.9900
O5—C5	1.4332 (18)	C7—H7A	0.9800
C1—C2	1.524 (2)	C7—H7B	0.9800
C1—H1	1.0000	C7—H7C	0.9800
C1—O1—C7	111.98 (12)	O4—C4—C5	111.62 (11)
C2—O2—H2O	109.5	C3—C4—C5	107.55 (11)
C3—O3—H3O	109.5	O4—C4—H4	108.3
C4—O4—H4O	109.5	C3—C4—H4	108.3
C1—O5—C5	112.93 (11)	C5—C4—H4	108.3
O1—C1—O5	112.36 (12)	O5—C5—C6	107.77 (12)
O1—C1—C2	108.51 (11)	O5—C5—C4	109.50 (11)
O5—C1—C2	110.34 (11)	C6—C5—C4	111.12 (12)
O1—C1—H1	108.5	O5—C5—H5	109.5
O5—C1—H1	108.5	C6—C5—H5	109.5
C2—C1—H1	108.5	C4—C5—H5	109.5
O2—C2—C1	111.48 (11)	C5—C6—I1	112.39 (11)
O2—C2—C3	112.18 (11)	C5—C6—H6A	109.1
C1—C2—C3	109.92 (11)	I1—C6—H6A	109.1
O2—C2—H2	107.7	C5—C6—H6B	109.1
C1—C2—H2	107.7	I1—C6—H6B	109.1
C3—C2—H2	107.7	H6A—C6—H6B	107.9
O3—C3—C2	110.89 (12)	O1—C7—H7A	109.5
O3—C3—C4	109.21 (11)	O1—C7—H7B	109.5
C2—C3—C4	110.34 (10)	H7A—C7—H7B	109.5
O3—C3—H3	108.8	O1—C7—H7C	109.5
C2—C3—H3	108.8	H7A—C7—H7C	109.5
C4—C3—H3	108.8	H7B—C7—H7C	109.5
O4—C4—C3	112.69 (11)
C7—O1—C1—O5	68.74 (15)	O3—C3—C4—O4	54.99 (14)
C7—O1—C1—C2	−168.99 (12)	C2—C3—C4—O4	−67.15 (14)
C5—O5—C1—O1	60.32 (15)	O3—C3—C4—C5	178.43 (11)
C5—O5—C1—C2	−60.91 (15)	C2—C3—C4—C5	56.30 (14)
O1—C1—C2—O2	56.83 (14)	C1—O5—C5—C6	−175.45 (12)
O5—C1—C2—O2	−179.68 (11)	C1—O5—C5—C4	63.56 (15)
O1—C1—C2—C3	−68.21 (14)	O4—C4—C5—O5	64.63 (14)
O5—C1—C2—C3	55.28 (14)	C3—C4—C5—O5	−59.47 (14)
O2—C2—C3—O3	59.55 (14)	O4—C4—C5—C6	−54.31 (16)
C1—C2—C3—O3	−175.82 (11)	C3—C4—C5—C6	−178.41 (13)
O2—C2—C3—C4	−179.31 (11)	O5—C5—C6—I1	56.19 (15)
C1—C2—C3—C4	−54.68 (14)	C4—C5—C6—I1	176.16 (10)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3i	0.84	1.90	2.7407 (15)	175
O3—H3O···O4i	0.84	2.01	2.8310 (16)	166
O4—H4O···O2ii	0.84	1.94	2.7529 (15)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3i	0.84	1.90	2.7407 (15)	175
O3—H3O⋯O4i	0.84	2.01	2.8310 (16)	166
O4—H4O⋯O2ii	0.84	1.94	2.7529 (15)	163

Symmetry codes: (i) ; (ii) .