2-Acetamido-2-de-oxy-3-O-β-d-galactopyranosyl-d-glucose dihydrate.

In the title compound, C(14)H(25)NO(11)·2H(2)O, the primary hydroxyl group connected to the anomeric C atom of the N-acetyl-β-d-glucopyran-ose residue exhibits positional disorder, with occupancy factors for the α and β anomers of 0.77 and 0.23, respectively. The two torsion angles (Φ and Ψ) and the bridge angle (τ) that describe conformation of the glycosidic linkage between the galactopyran-ose and glucopyran-ose rings are Φ = -81.6 (3)°, Ψ = 118.1 (2)° and τ = 115.2 (2)°. Two water mol-ecules stabilize the mol-ecular packing by forming hydrogen bonds with the saccharide residues.

Related literature

For the synthesis of the title compound, see: Kitaoka et al. (2005 ▶); Nishimoto & Kitaoka (2007a ▶,b ▶). For the conformation of saccharide rings, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C14H25NO11·2H2O

M = 419.38

Orthorhombic,

a = 8.284 (1) Å

b = 12.841 (1) Å

c = 17.503 (1) Å

V = 1861.9 (3) Å3

Z = 4

Synchrotron radiation

λ = 0.80000 Å

μ = 0.13 mm−1

T = 95 K

0.10 × 0.10 × 0.10 mm

Data collection

ADSC Quantum 210r diffractometer

Absorption correction: none

25787 measured reflections

2153 independent reflections

2046 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.115

S = 1.06

2153 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.31 e Å−3

Data collection: UGUI (Structural Biology Research Center, 2005 ▶); cell refinement: HKL-2000 (Otwinowski & Minor, 1997 ▶); data reduction: HKL-2000; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809024775/is2433sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024775/is2433Isup2.hkl

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

C14H25NO11·2H2O	F(000) = 896
Mr = 419.38	Dx = 1.496 Mg m−3
Orthorhombic, P212121	Synchrotron radiation, λ = 0.80000 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25787 reflections
a = 8.284 (1) Å	θ = 2.2–30.0°
b = 12.841 (1) Å	µ = 0.13 mm−1
c = 17.503 (1) Å	T = 95 K
V = 1861.9 (3) Å3	Block, colorless
Z = 4	0.10 × 0.10 × 0.10 mm

ADSC Quantum 210r diffractometer	2046 reflections with I > 2σ(I)
Radiation source: Photon Facrory NW12A	Rint = 0.047
silicon	θmax = 30.0°, θmin = 2.2°
Detector resolution: 9.7466 pixels mm-1	h = −10→10
ω scans	k = −16→16
25787 measured reflections	l = −21→21
2153 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difmap&geom
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0806P)2 + 0.7215P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2153 reflections	Δρmax = 0.27 e Å−3
264 parameters	Δρmin = −0.31 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.084 (6)

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	Occ. (<1)
C1	0.7021 (3)	0.32502 (19)	0.34879 (14)	0.0205 (5)
H1	0.8227	0.3214	0.3471	0.025*
C2	0.6435 (3)	0.4253 (2)	0.31127 (15)	0.0211 (5)
H2	0.5234	0.4232	0.3059	0.025*
C3	0.6921 (3)	0.52070 (19)	0.35853 (15)	0.0215 (5)
H3	0.8113	0.5310	0.3535	0.026*
C4	0.6518 (3)	0.5082 (2)	0.44263 (16)	0.0226 (6)
H4	0.7071	0.5646	0.4721	0.027*
C5	0.7119 (4)	0.4031 (2)	0.47122 (15)	0.0235 (6)
H5	0.8323	0.4017	0.4671	0.028*
C6	0.6658 (4)	0.3832 (2)	0.55375 (16)	0.0279 (6)
H61	0.6722	0.4494	0.5826	0.033*
H62	0.5526	0.3585	0.5559	0.033*
O1	0.6358 (2)	0.24111 (13)	0.30922 (11)	0.0217 (4)
O2	0.7150 (2)	0.43673 (14)	0.23805 (11)	0.0241 (4)
H2O	0.6648	0.4055	0.2024	0.029*
O3	0.6135 (3)	0.61167 (14)	0.33229 (11)	0.0261 (5)
H3O	0.6709	0.6420	0.2988	0.031*
O4	0.4818 (3)	0.51573 (15)	0.45519 (11)	0.0268 (5)
H4O	0.4508	0.5788	0.4331	0.032*
O5	0.6475 (2)	0.31996 (13)	0.42597 (10)	0.0219 (4)
O6	0.7678 (3)	0.30802 (14)	0.58916 (11)	0.0266 (5)
H6O	0.7491	0.2462	0.5742	0.032*
C7	0.8597 (3)	−0.00264 (19)	0.25298 (15)	0.0220 (5)
H71	0.8919	−0.0327	0.2025	0.026*	0.77
H72	0.9533	0.0120	0.2874	0.026*	0.23
C8	0.7699 (3)	0.10082 (19)	0.24040 (15)	0.0213 (5)
H8	0.6707	0.0870	0.2094	0.026*
C9	0.7191 (3)	0.14403 (19)	0.31837 (15)	0.0206 (5)
H9	0.8171	0.1549	0.3508	0.025*
C10	0.6100 (3)	0.06275 (19)	0.35568 (15)	0.0213 (5)
H10	0.5151	0.0491	0.3218	0.026*
C11	0.7058 (3)	−0.03748 (19)	0.36589 (15)	0.0218 (5)
H11	0.8047	−0.0211	0.3964	0.026*
C12	0.6157 (4)	−0.1242 (2)	0.40603 (16)	0.0248 (6)
H121	0.6855	−0.1866	0.4092	0.030*
H122	0.5888	−0.1022	0.4587	0.030*
O71	0.9959 (3)	0.01943 (18)	0.29538 (14)	0.0217 (5)	0.77
H71O	1.0752	−0.0218	0.2860	0.026*	0.77
O72	0.9226 (12)	−0.0517 (7)	0.1856 (5)	0.031 (2)	0.23
H72O	0.8861	−0.0216	0.1467	0.037*	0.23
O10	0.5548 (3)	0.09459 (15)	0.42885 (11)	0.0251 (5)
H10O	0.4729	0.1468	0.4241	0.030*
O11	0.7561 (2)	−0.07395 (14)	0.29198 (11)	0.0229 (4)
O12	0.4722 (3)	−0.1495 (2)	0.36648 (17)	0.0485 (7)
H12O	0.4325	−0.2091	0.3760	0.058*
N1	0.8734 (3)	0.17181 (16)	0.19831 (13)	0.0214 (5)
H1N	0.9621	0.1942	0.2205	0.026*
C13	0.8410 (3)	0.20474 (19)	0.12798 (16)	0.0220 (6)
O13	0.7167 (3)	0.18034 (14)	0.09211 (11)	0.0258 (4)
C14	0.9628 (4)	0.2771 (2)	0.09275 (17)	0.0312 (7)
H141	1.0519	0.2884	0.1287	0.047*
H142	0.9112	0.3438	0.0810	0.047*
H143	1.0048	0.2461	0.0456	0.047*
O1W	0.2143 (3)	0.39008 (16)	0.43738 (13)	0.0370 (6)
H11W	0.1688	0.3974	0.4806	0.044*
H12W	0.2950	0.4330	0.4398	0.044*
O2W	0.8087 (2)	0.72473 (14)	0.24058 (11)	0.0247 (4)
H21W	0.7630	0.7867	0.2498	0.030*
H22W	0.7901	0.7083	0.1942	0.030*

	U11	U22	U33	U12	U13	U23
C1	0.0228 (13)	0.0155 (11)	0.0234 (12)	−0.0008 (11)	0.0008 (11)	−0.0003 (9)
C2	0.0226 (13)	0.0174 (12)	0.0234 (12)	−0.0030 (10)	0.0052 (11)	0.0017 (10)
C3	0.0216 (12)	0.0146 (11)	0.0284 (13)	−0.0008 (10)	0.0015 (11)	0.0010 (10)
C4	0.0235 (13)	0.0161 (11)	0.0282 (13)	0.0002 (11)	0.0020 (11)	0.0000 (10)
C5	0.0270 (13)	0.0168 (11)	0.0266 (13)	−0.0004 (11)	−0.0002 (11)	0.0000 (10)
C6	0.0334 (16)	0.0232 (13)	0.0271 (14)	0.0061 (12)	0.0018 (12)	0.0011 (11)
O1	0.0240 (10)	0.0130 (8)	0.0280 (9)	0.0006 (8)	−0.0020 (8)	−0.0001 (7)
O2	0.0269 (10)	0.0221 (9)	0.0233 (9)	−0.0041 (8)	0.0020 (8)	0.0008 (7)
O3	0.0302 (11)	0.0151 (8)	0.0329 (10)	0.0033 (8)	0.0029 (9)	0.0043 (7)
O4	0.0272 (10)	0.0196 (9)	0.0336 (10)	0.0058 (8)	0.0065 (9)	0.0026 (8)
O5	0.0286 (10)	0.0147 (8)	0.0225 (9)	0.0002 (8)	0.0013 (8)	−0.0005 (7)
O6	0.0311 (11)	0.0193 (9)	0.0293 (10)	0.0021 (8)	−0.0036 (8)	0.0022 (8)
C7	0.0244 (13)	0.0165 (11)	0.0251 (12)	−0.0016 (11)	0.0001 (11)	0.0006 (10)
C8	0.0255 (13)	0.0146 (11)	0.0237 (12)	−0.0025 (11)	0.0002 (11)	0.0029 (10)
C9	0.0212 (12)	0.0138 (11)	0.0268 (12)	0.0010 (11)	−0.0009 (11)	0.0000 (10)
C10	0.0254 (14)	0.0160 (11)	0.0225 (12)	0.0003 (11)	0.0018 (11)	−0.0005 (10)
C11	0.0252 (13)	0.0162 (11)	0.0241 (12)	0.0004 (11)	0.0004 (11)	−0.0004 (10)
C12	0.0257 (14)	0.0182 (12)	0.0304 (13)	0.0001 (11)	−0.0022 (12)	0.0039 (11)
O71	0.0196 (11)	0.0169 (11)	0.0284 (12)	0.0029 (10)	−0.0022 (10)	−0.0015 (9)
O72	0.039 (5)	0.024 (4)	0.028 (4)	0.008 (4)	0.011 (4)	0.001 (4)
O10	0.0307 (11)	0.0200 (9)	0.0246 (9)	0.0042 (8)	0.0048 (8)	0.0018 (8)
O11	0.0289 (10)	0.0153 (8)	0.0246 (9)	−0.0021 (8)	0.0027 (8)	−0.0012 (7)
O12	0.0368 (13)	0.0384 (12)	0.0703 (17)	−0.0204 (11)	−0.0240 (13)	0.0300 (12)
N1	0.0208 (10)	0.0168 (10)	0.0268 (11)	−0.0020 (9)	0.0010 (9)	0.0007 (9)
C13	0.0235 (13)	0.0148 (11)	0.0278 (12)	−0.0005 (10)	−0.0005 (11)	0.0002 (10)
O13	0.0256 (10)	0.0232 (9)	0.0286 (10)	−0.0046 (8)	−0.0015 (8)	0.0015 (8)
C14	0.0330 (16)	0.0308 (14)	0.0298 (14)	−0.0107 (13)	0.0024 (12)	0.0058 (12)
O1W	0.0484 (14)	0.0261 (10)	0.0365 (12)	−0.0066 (11)	0.0090 (11)	−0.0014 (9)
O2W	0.0292 (10)	0.0169 (8)	0.0280 (9)	0.0031 (8)	−0.0015 (9)	−0.0020 (7)

C1—O1	1.394 (3)	C8—N1	1.452 (3)
C1—O5	1.426 (3)	C8—C9	1.532 (4)
C1—C2	1.525 (3)	C8—H8	1.0000
C1—H1	1.0000	C9—C10	1.528 (4)
C2—O2	1.419 (3)	C9—H9	1.0000
C2—C3	1.532 (3)	C10—O10	1.420 (3)
C2—H2	1.0000	C10—C11	1.523 (3)
C3—O3	1.414 (3)	C10—H10	1.0000
C3—C4	1.518 (4)	C11—O11	1.437 (3)
C3—H3	1.0000	C11—C12	1.514 (4)
C4—O4	1.429 (3)	C11—H11	1.0000
C4—C5	1.523 (3)	C12—O12	1.413 (4)
C4—H4	1.0000	C12—H121	0.9900
C5—O5	1.432 (3)	C12—H122	0.9900
C5—C6	1.516 (4)	O71—H71O	0.8594
C5—H5	1.0000	O72—H72O	0.8400
C6—O6	1.425 (3)	O10—H10O	0.9571
C6—H61	0.9900	O12—H12O	0.8497
C6—H62	0.9900	N1—C13	1.329 (4)
O1—C9	1.434 (3)	N1—H1N	0.8800
O2—H2O	0.8500	C13—O13	1.246 (4)
O3—H3O	0.8500	C13—C14	1.504 (4)
O4—H4O	0.9338	C14—H141	0.9800
O6—H6O	0.8499	C14—H142	0.9800
C7—O71	1.380 (4)	C14—H143	0.9800
C7—O11	1.428 (3)	O1W—H11W	0.8500
C7—O72	1.435 (9)	O1W—H12W	0.8676
C7—C8	1.538 (3)	O2W—H21W	0.8963
C7—H71	1.0000	O2W—H22W	0.8523
C7—H72	1.0000
O1—C1—O5	108.1 (2)	O72—C7—H72	107.2
O1—C1—C2	108.3 (2)	C8—C7—H72	107.4
O5—C1—C2	110.2 (2)	N1—C8—C9	112.7 (2)
O1—C1—H1	110.1	N1—C8—C7	109.2 (2)
O5—C1—H1	110.1	C9—C8—C7	108.5 (2)
C2—C1—H1	110.1	N1—C8—H8	108.8
O2—C2—C1	110.1 (2)	C9—C8—H8	108.8
O2—C2—C3	107.2 (2)	C7—C8—H8	108.8
C1—C2—C3	111.0 (2)	O1—C9—C10	110.9 (2)
O2—C2—H2	109.5	O1—C9—C8	110.3 (2)
C1—C2—H2	109.5	C10—C9—C8	107.2 (2)
C3—C2—H2	109.5	O1—C9—H9	109.5
O3—C3—C4	107.5 (2)	C10—C9—H9	109.5
O3—C3—C2	111.3 (2)	C8—C9—H9	109.5
C4—C3—C2	112.4 (2)	O10—C10—C11	107.8 (2)
O3—C3—H3	108.5	O10—C10—C9	112.3 (2)
C4—C3—H3	108.5	C11—C10—C9	108.6 (2)
C2—C3—H3	108.5	O10—C10—H10	109.4
O4—C4—C3	111.0 (2)	C11—C10—H10	109.4
O4—C4—C5	109.4 (2)	C9—C10—H10	109.4
C3—C4—C5	109.9 (2)	O11—C11—C12	108.7 (2)
O4—C4—H4	108.8	O11—C11—C10	108.7 (2)
C3—C4—H4	108.8	C12—C11—C10	114.8 (2)
C5—C4—H4	108.8	O11—C11—H11	108.2
O5—C5—C6	107.9 (2)	C12—C11—H11	108.2
O5—C5—C4	110.9 (2)	C10—C11—H11	108.2
C6—C5—C4	112.3 (2)	O12—C12—C11	110.9 (2)
O5—C5—H5	108.5	O12—C12—H121	109.5
C6—C5—H5	108.5	C11—C12—H121	109.5
C4—C5—H5	108.5	O12—C12—H122	109.5
O6—C6—C5	112.3 (2)	C11—C12—H122	109.5
O6—C6—H61	109.2	H121—C12—H122	108.0
C5—C6—H61	109.2	C7—O71—H71O	113.3
O6—C6—H62	109.2	C7—O72—H72O	109.5
C5—C6—H62	109.2	C10—O10—H10O	110.6
H61—C6—H62	107.9	C7—O11—C11	113.28 (19)
C1—O1—C9	115.2 (2)	C12—O12—H12O	115.9
C2—O2—H2O	114.2	C13—N1—C8	123.4 (2)
C3—O3—H3O	110.2	C13—N1—H1N	118.3
C4—O4—H4O	105.5	C8—N1—H1N	118.3
C1—O5—C5	111.8 (2)	O13—C13—N1	123.6 (3)
C6—O6—H6O	113.0	O13—C13—C14	120.2 (2)
O71—C7—O11	111.5 (2)	N1—C13—C14	116.2 (2)
O11—C7—O72	109.2 (4)	C13—C14—H141	109.5
O71—C7—C8	107.1 (2)	C13—C14—H142	109.5
O11—C7—C8	109.4 (2)	H141—C14—H142	109.5
O72—C7—C8	115.9 (4)	C13—C14—H143	109.5
O71—C7—H71	109.6	H141—C14—H143	109.5
O11—C7—H71	109.6	H142—C14—H143	109.5
C8—C7—H71	109.6	H11W—O1W—H12W	103.1
O11—C7—H72	107.4	H21W—O2W—H22W	108.4
O1—C1—C2—O2	−69.5 (3)	O11—C7—C8—C9	58.8 (3)
O5—C1—C2—O2	172.4 (2)	O72—C7—C8—C9	−177.2 (5)
O1—C1—C2—C3	171.9 (2)	C1—O1—C9—C10	118.0 (2)
O5—C1—C2—C3	53.9 (3)	C1—O1—C9—C8	−123.3 (2)
O2—C2—C3—O3	70.7 (3)	N1—C8—C9—O1	58.5 (3)
C1—C2—C3—O3	−169.0 (2)	C7—C8—C9—O1	179.6 (2)
O2—C2—C3—C4	−168.6 (2)	N1—C8—C9—C10	179.3 (2)
C1—C2—C3—C4	−48.3 (3)	C7—C8—C9—C10	−59.5 (3)
O3—C3—C4—O4	50.3 (3)	O1—C9—C10—O10	−59.4 (3)
C2—C3—C4—O4	−72.6 (3)	C8—C9—C10—O10	−179.9 (2)
O3—C3—C4—C5	171.5 (2)	O1—C9—C10—C11	−178.5 (2)
C2—C3—C4—C5	48.6 (3)	C8—C9—C10—C11	61.0 (3)
O4—C4—C5—O5	66.6 (3)	O10—C10—C11—O11	177.2 (2)
C3—C4—C5—O5	−55.5 (3)	C9—C10—C11—O11	−60.9 (3)
O4—C4—C5—C6	−54.2 (3)	O10—C10—C11—C12	55.2 (3)
C3—C4—C5—C6	−176.4 (2)	C9—C10—C11—C12	177.1 (2)
O5—C5—C6—O6	79.5 (3)	O11—C11—C12—O12	−64.1 (3)
C4—C5—C6—O6	−157.9 (2)	C10—C11—C12—O12	57.9 (3)
O5—C1—O1—C9	−81.6 (3)	O71—C7—O11—C11	57.6 (3)
C2—C1—O1—C9	159.0 (2)	O72—C7—O11—C11	171.4 (5)
O1—C1—O5—C5	179.3 (2)	C8—C7—O11—C11	−60.7 (3)
C2—C1—O5—C5	−62.6 (3)	C12—C11—O11—C7	−172.7 (2)
C6—C5—O5—C1	−172.6 (2)	C10—C11—O11—C7	61.8 (3)
C4—C5—O5—C1	64.0 (3)	C9—C8—N1—C13	−125.0 (3)
O71—C7—C8—N1	61.1 (3)	C7—C8—N1—C13	114.2 (3)
O11—C7—C8—N1	−178.0 (2)	C8—N1—C13—O13	2.1 (4)
O72—C7—C8—N1	−53.9 (5)	C8—N1—C13—C14	−179.2 (2)
O71—C7—C8—C9	−62.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2Wi	0.88	2.05	2.923 (3)	169
O2—H2O···O12ii	0.85	1.80	2.642 (3)	170
O3—H3O···O2W	0.85	1.86	2.702 (3)	169
O4—H4O···O13ii	0.93	1.95	2.803 (3)	150
O6—H6O···O1Wiii	0.85	1.79	2.624 (3)	168
O10—H10O···O6iv	0.96	1.81	2.705 (3)	154
O1W—H11W···O10iv	0.85	1.85	2.696 (3)	175
O12—H12O···O13v	0.85	1.96	2.784 (3)	162
O1W—H12W···O4	0.87	1.90	2.759 (3)	173
O2W—H21W···O11vi	0.90	1.94	2.772 (3)	154
O2W—H22W···O6vii	0.85	1.91	2.757 (3)	171
O71—H71O···O2i	0.86	1.87	2.683 (3)	159
O72—H72O···O1Wv	0.84	2.04	2.545 (9)	119

C1—O1—C9

115.2 (2)

O5—C1—O1—C9	−81.6 (3)
C2—C1—O1—C9	159.0 (2)
C1—O1—C9—C10	118.0 (2)
C1—O1—C9—C8	−123.3 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2Wi	0.88	2.05	2.923 (3)	169
O2—H2O⋯O12ii	0.85	1.80	2.642 (3)	170
O3—H3O⋯O2W	0.85	1.86	2.702 (3)	169
O4—H4O⋯O13ii	0.93	1.95	2.803 (3)	150
O6—H6O⋯O1Wiii	0.85	1.79	2.624 (3)	168
O10—H10O⋯O6iv	0.96	1.81	2.705 (3)	154
O1W—H11W⋯O10iv	0.85	1.85	2.696 (3)	175
O12—H12O⋯O13v	0.85	1.96	2.784 (3)	162
O1W—H12W⋯O4	0.87	1.90	2.759 (3)	173
O2W—H21W⋯O11vi	0.90	1.94	2.772 (3)	154
O2W—H22W⋯O6vii	0.85	1.91	2.757 (3)	171
O71—H71O⋯O2i	0.86	1.87	2.683 (3)	159
O72—H72O⋯O1Wv	0.84	2.04	2.545 (9)	119

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .