Methyl β-lactoside [methyl β-d-galacto­pyranosyl-(1→4)-β-d-gluco­pyran­oside] monohydrate: a solvomorphism study

Lin, J.; Oliver, A.G.; Serianni, A.S.

doi:10.1107/S2053229621009499

Methyl β-lactoside [methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside] monohydrate: a solvomorphism study

Methyl β-lactoside [methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside] monohydrate, C₁₃H₂₄O₁₁·H₂O, (I), was obtained via spontaneous transformation of methyl β-lactoside methanol solvate, (II), during air-drying. Cremer–Pople puckering parameters indicate that the β-D-Galp (β-D-galactopyranosyl) and β-D-Glcp (β-D-glucopyranosyl) rings in (I) adopt slightly distorted ⁴C₁ chair conformations, with the former distorted towards a boat form (B_C1,C4) and the latter towards a twist-boat form (^O5S_C2). Puckering parameters for (I) and (II) indicate that the conformation of the βGalp ring is slightly more affected than the βGlcp ring by the solvomorphism. Conformations of the terminal O-glycosidic linkages in (I) and (II) are virtually identical, whereas those of the internal O-glycosidic linkage show torsion-angle changes of 6° in both C—O bonds. The exocyclic hydroxymethyl group in the βGalp residue adopts a gt conformation (C4′ anti to O6′) in both (I) and (II), whereas that in the βGlcp residue adopts a gg (gauche–gauche) conformation (H5 anti to O6) in (II) and a gt (gauche–trans) conformation (C4 anti to O6) in (I). The latter conformational change is critical to the solvomorphism in that it allows water to participate in three hydrogen bonds in (I) as opposed to only two hydrogen bonds in (II), potentially producing a more energetically stable structure for (I) than for (II). Visual inspection of the crystalline lattice of (II) reveals channels in which methanol solvent resides and through which solvent might exchange during solvomorphism. These channels are less apparent in the crystalline lattice of (I).

Keywords: methyl β-lactoside monohydrate; methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside monohydrate; crystal transformation; solvomorphism; X-ray crystal structure; chemical synthesis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229621009499/eq3002sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229621009499/eq3002Isup2.hkl Contains datablock I
	Portable Document Format (PDF) file https://doi.org/10.1107/S2053229621009499/eq3002sup3.pdf Statistical analysis of bond distances, PXRD diffractograms and void space analysis/figures

CCDC reference: 2109224

Computing details top

Data collection: APEX3 (Bruker, 2018); cell refinement: SAINT (Bruker, 2018); data reduction: SAINT (Bruker, 2018); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015b).

Methyl β-lactoside monohydrate top

Crystal data top

C₁₃H₂₄O₁₁·H₂O	F(000) = 400
M_r = 374.34	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54178 Å
a = 4.6250 (1) Å	Cell parameters from 9961 reflections
b = 24.0147 (7) Å	θ = 3.7–70.6°
c = 7.6617 (2) Å	µ = 1.18 mm⁻¹
β = 105.595 (1)°	T = 120 K
V = 819.64 (4) Å³	Tablet, colourless
Z = 2	0.18 × 0.17 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	3056 independent reflections
Radiation source: Ius micro-focus	3031 reflections with I > 2σ(I)
Detector resolution: 7.41 pixels mm^-1	R_int = 0.025
φ and ω scans	θ_max = 70.6°, θ_min = 3.7°
Absorption correction: numerical (SADABS; Krause et al., 2015)	h = −5→5
T_min = 0.581, T_max = 0.738	k = −29→29
14059 measured reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.071	w = 1/[σ²(F_o²) + (0.045P)² + 0.1553P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3056 reflections	Δρ_max = 0.31 e Å⁻³
263 parameters	Δρ_min = −0.16 e Å⁻³
2 restraints	Absolute structure: Flack x determined using 1459 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: 0.05 (4)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.6945 (4)	0.69849 (7)	1.0028 (2)	0.0275 (4)
O2	0.8779 (4)	0.59193 (7)	1.1369 (2)	0.0273 (3)
H2O	0.965 (7)	0.5620 (14)	1.139 (4)	0.028 (7)*
O3	0.5847 (4)	0.50682 (7)	0.8846 (2)	0.0267 (3)
H3O	0.621 (7)	0.4792 (15)	0.838 (4)	0.030 (8)*
O5	0.5942 (4)	0.66710 (6)	0.7138 (2)	0.0220 (3)
O6	0.6390 (4)	0.69673 (7)	0.3572 (2)	0.0326 (4)
H6O	0.669 (8)	0.6929 (14)	0.249 (5)	0.042 (9)*
O1'	0.6438 (3)	0.53275 (6)	0.5092 (2)	0.0213 (3)
O2'	0.2953 (4)	0.50780 (7)	0.1565 (2)	0.0242 (3)
H2O'	0.350 (10)	0.5057 (19)	0.072 (6)	0.058 (12)*
O3'	0.2417 (4)	0.39315 (7)	0.0577 (2)	0.0237 (3)
H3O'	0.382 (10)	0.3860 (17)	0.042 (5)	0.046 (11)*
O4'	0.7291 (3)	0.35632 (7)	0.3451 (2)	0.0216 (3)
H4O'	0.764 (6)	0.3249 (13)	0.359 (3)	0.013 (6)*
O5'	0.6327 (3)	0.44224 (6)	0.5922 (2)	0.0205 (3)
O6'	0.6741 (4)	0.37161 (8)	0.8886 (2)	0.0309 (4)
H6O'	0.873 (8)	0.3796 (15)	0.944 (5)	0.040 (8)*
C1	0.7704 (5)	0.65762 (9)	0.8945 (3)	0.0224 (4)
H1	0.989103	0.659580	0.901284	0.027*
C2	0.6930 (5)	0.60125 (9)	0.9609 (3)	0.0212 (4)
H2	0.480366	0.602811	0.967917	0.025*
C3	0.7160 (5)	0.55488 (9)	0.8288 (3)	0.0207 (4)
H3	0.932836	0.547190	0.840480	0.025*
C4	0.5624 (5)	0.57059 (9)	0.6322 (3)	0.0193 (4)
H4	0.339676	0.570235	0.612076	0.023*
C5	0.6628 (5)	0.62815 (9)	0.5886 (3)	0.0207 (4)
H5	0.884366	0.627842	0.603719	0.025*
C6	0.5041 (5)	0.64700 (9)	0.3986 (3)	0.0241 (4)
H6A	0.517498	0.617525	0.310737	0.029*
H6B	0.289288	0.653766	0.389090	0.029*
C7	0.8300 (9)	0.75158 (11)	0.9912 (4)	0.0445 (7)
HA	0.804741	0.761126	0.863563	0.067*
HC	1.044419	0.749864	1.053992	0.067*
HB	0.733355	0.780040	1.047915	0.067*
C1'	0.4761 (5)	0.48398 (9)	0.4699 (3)	0.0190 (4)
H1'	0.270949	0.489827	0.486252	0.023*
C2'	0.4547 (5)	0.46614 (9)	0.2760 (3)	0.0191 (4)
H2'	0.660667	0.461738	0.259442	0.023*
C3'	0.2871 (4)	0.41071 (9)	0.2399 (3)	0.0192 (4)
H3'	0.084205	0.416873	0.259437	0.023*
C4'	0.4446 (5)	0.36713 (8)	0.3764 (3)	0.0194 (4)
H4'	0.322879	0.332145	0.358122	0.023*
C5'	0.4756 (5)	0.38959 (9)	0.5674 (3)	0.0194 (4)
H5'	0.271275	0.394969	0.585597	0.023*
C6'	0.6551 (5)	0.35079 (10)	0.7124 (3)	0.0234 (4)
H6B'	0.558661	0.313657	0.698274	0.028*
H6A'	0.859855	0.346437	0.697257	0.028*
O1W	0.8826 (4)	0.24832 (8)	0.3889 (3)	0.0390 (4)
H1WA	0.738 (9)	0.2209 (19)	0.366 (7)	0.078 (14)*
H1WB	1.050 (8)	0.2317 (16)	0.471 (5)	0.054 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0444 (10)	0.0198 (8)	0.0198 (8)	−0.0016 (7)	0.0108 (7)	−0.0025 (6)
O2	0.0329 (8)	0.0269 (8)	0.0197 (7)	0.0076 (7)	0.0026 (6)	−0.0022 (6)
O3	0.0421 (9)	0.0189 (7)	0.0216 (7)	−0.0016 (7)	0.0130 (7)	−0.0021 (6)
O5	0.0288 (8)	0.0198 (7)	0.0172 (7)	0.0032 (6)	0.0057 (6)	−0.0007 (6)
O6	0.0498 (11)	0.0259 (9)	0.0227 (8)	−0.0039 (8)	0.0107 (8)	0.0009 (7)
O1'	0.0233 (7)	0.0201 (7)	0.0216 (7)	−0.0016 (6)	0.0084 (6)	−0.0038 (6)
O2'	0.0267 (8)	0.0250 (7)	0.0202 (7)	0.0069 (6)	0.0053 (6)	0.0029 (6)
O3'	0.0204 (8)	0.0322 (8)	0.0180 (7)	−0.0005 (6)	0.0044 (6)	−0.0056 (6)
O4'	0.0205 (7)	0.0195 (8)	0.0272 (8)	0.0016 (6)	0.0104 (6)	−0.0009 (6)
O5'	0.0218 (7)	0.0196 (7)	0.0184 (7)	−0.0022 (5)	0.0024 (6)	−0.0008 (5)
O6'	0.0220 (8)	0.0529 (11)	0.0177 (7)	−0.0008 (7)	0.0051 (6)	−0.0018 (7)
C1	0.0252 (10)	0.0226 (10)	0.0187 (10)	−0.0012 (8)	0.0046 (8)	−0.0023 (8)
C2	0.0216 (10)	0.0229 (11)	0.0186 (10)	0.0007 (8)	0.0049 (8)	−0.0013 (8)
C3	0.0227 (10)	0.0195 (10)	0.0198 (10)	0.0008 (7)	0.0055 (8)	0.0001 (7)
C4	0.0213 (10)	0.0200 (9)	0.0171 (10)	0.0007 (8)	0.0059 (8)	−0.0023 (8)
C5	0.0233 (10)	0.0202 (10)	0.0190 (10)	0.0011 (8)	0.0062 (8)	−0.0029 (8)
C6	0.0295 (11)	0.0234 (11)	0.0190 (10)	0.0004 (8)	0.0059 (8)	−0.0011 (8)
C7	0.083 (2)	0.0225 (12)	0.0317 (13)	−0.0111 (13)	0.0212 (14)	−0.0059 (10)
C1'	0.0189 (9)	0.0184 (9)	0.0197 (10)	−0.0005 (8)	0.0051 (8)	−0.0017 (7)
C2'	0.0174 (9)	0.0211 (9)	0.0183 (9)	0.0012 (8)	0.0037 (7)	0.0005 (8)
C3'	0.0152 (9)	0.0245 (10)	0.0182 (10)	−0.0014 (7)	0.0050 (8)	−0.0032 (8)
C4'	0.0169 (9)	0.0204 (10)	0.0222 (10)	−0.0023 (7)	0.0074 (8)	−0.0024 (8)
C5'	0.0196 (9)	0.0195 (9)	0.0200 (9)	−0.0027 (7)	0.0068 (8)	−0.0013 (8)
C6'	0.0246 (10)	0.0263 (10)	0.0195 (9)	−0.0019 (8)	0.0062 (8)	0.0012 (8)
O1W	0.0337 (9)	0.0249 (8)	0.0568 (12)	0.0012 (7)	0.0094 (9)	0.0071 (8)

Geometric parameters (Å, º) top

O1—C1	1.390 (3)	C3—C4	1.530 (3)
O1—C7	1.434 (3)	C3—H3	1.0000
O2—C2	1.407 (3)	C4—C5	1.524 (3)
O2—H2O	0.82 (3)	C4—H4	1.0000
O3—C3	1.422 (3)	C5—C6	1.512 (3)
O3—H3O	0.79 (4)	C5—H5	1.0000
O5—C1	1.423 (3)	C6—H6A	0.9900
O5—C5	1.435 (2)	C6—H6B	0.9900
O6—C6	1.422 (3)	C7—HA	0.9800
O6—H6O	0.88 (4)	C7—HC	0.9800
O1'—C1'	1.392 (3)	C7—HB	0.9800
O1'—C4	1.430 (2)	C1'—C2'	1.523 (3)
O2'—C2'	1.421 (3)	C1'—H1'	1.0000
O2'—H2O'	0.76 (5)	C2'—C3'	1.528 (3)
O3'—C3'	1.419 (3)	C2'—H2'	1.0000
O3'—H3O'	0.71 (4)	C3'—C4'	1.520 (3)
O4'—C4'	1.424 (3)	C3'—H3'	1.0000
O4'—H4O'	0.77 (3)	C4'—C5'	1.530 (3)
O5'—C1'	1.429 (3)	C4'—H4'	1.0000
O5'—C5'	1.445 (3)	C5'—C6'	1.515 (3)
O6'—C6'	1.420 (3)	C5'—H5'	1.0000
O6'—H6O'	0.93 (4)	C6'—H6B'	0.9900
C1—C2	1.522 (3)	C6'—H6A'	0.9900
C1—H1	1.0000	O1W—H1WA	0.92 (4)
C2—C3	1.527 (3)	O1W—H1WB	0.95 (3)
C2—H2	1.0000

C1—O1—C7	113.95 (19)	C5—C6—H6B	109.7
C2—O2—H2O	109 (2)	H6A—C6—H6B	108.2
C3—O3—H3O	113 (2)	O1—C7—HA	109.5
C1—O5—C5	111.99 (16)	O1—C7—HC	109.5
C6—O6—H6O	108 (2)	HA—C7—HC	109.5
C1'—O1'—C4	116.57 (16)	O1—C7—HB	109.5
C2'—O2'—H2O'	106 (3)	HA—C7—HB	109.5
C3'—O3'—H3O'	110 (3)	HC—C7—HB	109.5
C4'—O4'—H4O'	108.7 (19)	O1'—C1'—O5'	107.07 (16)
C1'—O5'—C5'	112.29 (15)	O1'—C1'—C2'	109.53 (16)
C6'—O6'—H6O'	108 (2)	O5'—C1'—C2'	109.31 (16)
O1—C1—O5	107.31 (17)	O1'—C1'—H1'	110.3
O1—C1—C2	107.97 (17)	O5'—C1'—H1'	110.3
O5—C1—C2	110.05 (17)	C2'—C1'—H1'	110.3
O1—C1—H1	110.5	O2'—C2'—C1'	108.48 (16)
O5—C1—H1	110.5	O2'—C2'—C3'	110.28 (16)
C2—C1—H1	110.5	C1'—C2'—C3'	108.58 (16)
O2—C2—C1	108.96 (18)	O2'—C2'—H2'	109.8
O2—C2—C3	112.73 (18)	C1'—C2'—H2'	109.8
C1—C2—C3	111.25 (18)	C3'—C2'—H2'	109.8
O2—C2—H2	107.9	O3'—C3'—C4'	112.89 (18)
C1—C2—H2	107.9	O3'—C3'—C2'	111.77 (17)
C3—C2—H2	107.9	C4'—C3'—C2'	110.44 (16)
O3—C3—C2	106.35 (17)	O3'—C3'—H3'	107.1
O3—C3—C4	111.91 (18)	C4'—C3'—H3'	107.1
C2—C3—C4	112.09 (17)	C2'—C3'—H3'	107.1
O3—C3—H3	108.8	O4'—C4'—C3'	107.68 (17)
C2—C3—H3	108.8	O4'—C4'—C5'	111.86 (17)
C4—C3—H3	108.8	C3'—C4'—C5'	108.64 (17)
O1'—C4—C5	106.40 (16)	O4'—C4'—H4'	109.5
O1'—C4—C3	110.95 (17)	C3'—C4'—H4'	109.5
C5—C4—C3	110.59 (17)	C5'—C4'—H4'	109.5
O1'—C4—H4	109.6	O5'—C5'—C6'	106.55 (16)
C5—C4—H4	109.6	O5'—C5'—C4'	110.39 (16)
C3—C4—H4	109.6	C6'—C5'—C4'	112.11 (17)
O5—C5—C6	108.13 (17)	O5'—C5'—H5'	109.2
O5—C5—C4	108.03 (16)	C6'—C5'—H5'	109.2
C6—C5—C4	112.65 (17)	C4'—C5'—H5'	109.2
O5—C5—H5	109.3	O6'—C6'—C5'	111.23 (18)
C6—C5—H5	109.3	O6'—C6'—H6B'	109.4
C4—C5—H5	109.3	C5'—C6'—H6B'	109.4
O6—C6—C5	109.72 (18)	O6'—C6'—H6A'	109.4
O6—C6—H6A	109.7	C5'—C6'—H6A'	109.4
C5—C6—H6A	109.7	H6B'—C6'—H6A'	108.0
O6—C6—H6B	109.7	H1WA—O1W—H1WB	104 (4)

C7—O1—C1—O5	−78.2 (2)	C4—C5—C6—O6	−171.25 (17)
C7—O1—C1—C2	163.2 (2)	C4—O1'—C1'—O5'	−93.96 (19)
C5—O5—C1—O1	177.92 (16)	C4—O1'—C1'—C2'	147.62 (17)
C5—O5—C1—C2	−64.8 (2)	C5'—O5'—C1'—O1'	178.56 (15)
O1—C1—C2—O2	−65.4 (2)	C5'—O5'—C1'—C2'	−62.9 (2)
O5—C1—C2—O2	177.76 (18)	O1'—C1'—C2'—O2'	−63.7 (2)
O1—C1—C2—C3	169.71 (17)	O5'—C1'—C2'—O2'	179.31 (15)
O5—C1—C2—C3	52.9 (2)	O1'—C1'—C2'—C3'	176.47 (16)
O2—C2—C3—O3	68.3 (2)	O5'—C1'—C2'—C3'	59.5 (2)
C1—C2—C3—O3	−168.95 (17)	O2'—C2'—C3'—O3'	57.6 (2)
O2—C2—C3—C4	−169.09 (18)	C1'—C2'—C3'—O3'	176.29 (16)
C1—C2—C3—C4	−46.3 (2)	O2'—C2'—C3'—C4'	−175.87 (16)
C1'—O1'—C4—C5	−154.47 (17)	C1'—C2'—C3'—C4'	−57.1 (2)
C1'—O1'—C4—C3	85.2 (2)	O3'—C3'—C4'—O4'	60.0 (2)
O3—C3—C4—O1'	−73.8 (2)	C2'—C3'—C4'—O4'	−66.0 (2)
C2—C3—C4—O1'	166.84 (17)	O3'—C3'—C4'—C5'	−178.70 (16)
O3—C3—C4—C5	168.41 (16)	C2'—C3'—C4'—C5'	55.4 (2)
C2—C3—C4—C5	49.0 (2)	C1'—O5'—C5'—C6'	−176.46 (16)
C1—O5—C5—C6	−170.91 (17)	C1'—O5'—C5'—C4'	61.6 (2)
C1—O5—C5—C4	66.9 (2)	O4'—C4'—C5'—O5'	62.4 (2)
O1'—C4—C5—O5	−178.01 (15)	C3'—C4'—C5'—O5'	−56.3 (2)
C3—C4—C5—O5	−57.4 (2)	O4'—C4'—C5'—C6'	−56.2 (2)
O1'—C4—C5—C6	62.6 (2)	C3'—C4'—C5'—C6'	−174.95 (17)
C3—C4—C5—C6	−176.81 (18)	O5'—C5'—C6'—O6'	60.8 (2)
O5—C5—C6—O6	69.4 (2)	C4'—C5'—C6'—O6'	−178.35 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2′—H2O′···O3ⁱ	0.76 (5)	2.02 (5)	2.763 (2)	167 (5)
O2—H2O···O2′ⁱⁱ	0.82 (3)	1.98 (3)	2.770 (2)	160 (3)
O3′—H3O′···O6′ⁱ	0.71 (4)	2.04 (4)	2.709 (2)	156 (4)
O3—H3O···O5′	0.79 (4)	2.10 (4)	2.782 (2)	145 (3)
O3—H3O···O6′	0.79 (4)	2.61 (4)	3.272 (3)	142 (3)
O4′—H4O′···O1W	0.77 (3)	1.92 (3)	2.686 (3)	175 (3)
O6′—H6O′···O3′ⁱⁱ	0.93 (4)	1.72 (4)	2.647 (2)	177 (3)
O6—H6O···O1ⁱ	0.88 (4)	1.92 (4)	2.795 (2)	169 (3)
O1W—H1WA···O5ⁱⁱⁱ	0.92 (4)	1.97 (4)	2.890 (2)	172 (5)
O1W—H1WB···O6^iv	0.95 (3)	1.87 (3)	2.811 (3)	176 (4)

Symmetry codes: (i) x, y, z−1; (ii) x+1, y, z+1; (iii) −x+1, y−1/2, −z+1; (iv) −x+2, y−1/2, −z+1.

Cremer–Pople structural parameters for the βGlcp and βGalp rings in (I) and (II) top

Compound/Residue	φ (°)	θ (°)	Q (Å)	q₂	q₃
(I)/βGalp	70.168	1.912	0.594	0.020	0.594
(I)/βGlcp	340.062	9.947	0.569	0.098	0.560
(II)/βGalp	28.171	4.675	0.595	0.049	0.593
(II)/βGlcp	341.473	11.993	0.558	0.116	0.546

Select structural parameters (Å, °) in (I) and (II) top

		(I)	(II)
	C—C bond lengths^a
1	C1'—C2'	1.524 (3)	1.527 (3)
2	C2'—C3'	1.528 (3)	1.531 (3)
3	C3'—C4'	1.520 (3)	1.521 (3)
4	C4'—-C5'	1.530 (3)	1.521 (3)
5	C5'–C6'	1.515 (3)	1.511 (3)
6	C1—C2	1.522 (3)	1.516 (4)
7	C2—C3	1.528 (3)	1.519 (3)
8	C3—C4	1.530 (3)	1.531 (3)
9	C4—C5	1.524 (3)	1.530 (3)
10	C5—C6	1.512 (3)	1.508 (3)

	C—O bond lengths
1	C1'—O1'	1.392 (3)	1.387 (3)
2	C1'—O5'	1.429 (2)	1.425 (3)
3	C2'—O2'	1.421 (3)	1.414 (3)
4	C3'—O3'	1.419 (3)	1.422 (3)
5	C4'—O4'	1.423 (3)	1.423 (3)
6	C5'—O5'	1.445 (3)	1.432 (3)
7	C6'—O6'	1.420 (3)	1.426 (3)
8	C1—O1	1.390 (3)	1.384 (3)
9	C1—O5	1.423 (2)	1.413 (3)
10	C2—O2	1.407 (2)	1.418 (3)
11	C3—O3	1.422 (3)	1.421 (3)
12	O1'—C4	1.431 (3)	1.437 (3)
13	C5—O5	1.435 (3)	1.428 (3)
14	C6—O6	1.422 (3)	1.424 (3)

	Internuclear distances
	O3_d···O5'	2.782 (2)	2.764 (2)
	O3_d···O6'ⁱⁱ	3.272 (3)	2.935 (3)
	H₂O···O5_aⁱ	2.890 (2)	–
	H₂O···O6_a^iv	2.811 (3)	–
	O4'_d···H₂O	2.686 (3)	–
	CH₃OH···O6_a	–	2.727 (3)
	O4'_d···CH₃OH	–	2.686 (11)

	Bond angles
	C5—O5—C1	112.0 (2)	112.0 (2)
	C5'—O5'—C1'	112.3 (2)	112.3 (2)
	C1'—O1'—C4	116.5 (2)	116.2 (2)
	C1—O1—CH₃	114.0 (2)	113.7 (2)

	Torsion angles
	C1—C2—C3—C4	-46.4 (2)	-44.2 (3)
	C1—O5—C5—C4	66.9 (2)	67.6 (2)
	C1'—C2'—C3'—C4'	-7.1 (2)	-54.8 (2)
	C1'—O5'—C5'—C4'	61.6 (2)	65.0 (2)
	O5—C1—O1—CH₃ (φ)	-78.2 (2)	-77.3 (3)
	C2—C1—O1—CH₃ (φ)	163.2 (2)	164.2 (2)
	H1—C1—O1—CH₃ (φ)	42.2	44.1 (4)
	O5'—C1'—O1'—C4 (φ')	-94.0 (2)	-88.4 (2)
	C2'—C1'—O1'—C4 (φ')	147.6 (2)	153.8 (2)
	H1'—C1'—O1'—C4 (φ')	26.1	31.9 (3)
	C1'—O1'—C4—C3 (ψ')	85.2 (2)	78.4 (2)
	C1'—O1'—C4—C5 (ψ')	-154.5 (2)	-161.3 (2)
	C1'—O1'—C4—H4 (ψ')	-36.0	-43.7 (3)
	O5—C5—C6—O6 (ω)	69.4 (2) [gt]	-54.6 (2) [gg]
	C4—C5—C6—O6 (ω)	-171.3 (2) [gt]	66.4 (3) [gg]
	O5'—C5'—C6'—O6' (ω)	60.8 (2) [gt]	57.3 (2) [gt]
	C4'—C5'—C6'—O6' (ω')	-178.4 (2) [gt]	177.8 (2) [gt]
	C1—C2—O2—H	-125.6	-123.4
	C2—C3—O3—H	-166.6	-159.0
	C5—C6—O6—H	133.0	-123.1
	C1'—C2'—O2'—H	153.5	143.4
	C2'–C3'–O3'—H	68.1	44.9
	C3'—C4'—O4'—H	-142.2	-112.3
	C5'—C6'—O6'—H	-115.3	-132.5

Notes: (a) C—C and C—O bond length numbers shown in the left-most column were used to plot the data in Fig. S1 (in the supporting information). Subscript `a' denotes an acceptor site and subscript `d' the donor atom in the hydrogen bond. [Symmetry codes: (i) -x+1, y-1/2, -z+1; (ii) x+1, y, z+1; (iv) x, y, z+1.]

Hydrogen-bond geometry (Å, °) of (I) and (II) top

Compound	D—H···A	D—H	H···A (Å)	D···A	D—H···A
(I)	Sugar–solvent interactions
	O1W—H1WA···O5ⁱ	0.92 (4)	1.97 (4)	2.890 (3)	172 (5)
	O1W—H1WB···O6^iv	0.95 (3)	1.87 (4)	2.811 (3)	176 (4)
	O4'—H4O'···O1W	0.77 (3)	1.92 (3)	2.686 (3)	175 (3)
	Sugar–sugar interactions
	O2—H2O···O2'ⁱⁱⁱ	0.83 (3)	1.98 (3)	2.771 (2)	160 (3)
	O3—H3O···O5'	0.79 (4)	2.10 (4)	2.782 (2)	145 (3)
	O6—H6O···O1ⁱⁱ	0.88 (4)	1.92 (4)	2.795 (2)	169 (3)
	O2'—H2O'···O3ⁱⁱ	0.76 (5)	2.02 (5)	2.763 (2)	167 (5)
	O3'—H3O'···O6'ⁱⁱ	0.71 (4)	2.04 (4)	2.709 (2)	156 (4)
	O6'—H6O'···O3'ⁱⁱⁱ	0.93 (4)	1.72 (4)	2.647 (2)	177 (3)

(II)	Sugar–solvent interactions
	O4'—H4'O···O11ⁱ	0.82 (1)	1.87	2.686 (3)	171
	O11—H11O···O6	0.82 (1)	1.93	2.727 (3)	164
	Sugar–sugar interactions
	O2—H2O···O2'ⁱⁱⁱ	0.82 (2)	1.96	2.757 (3)	163
	O3—H3O···O5'	0.82 (2)	2.08	2.764 (2)	141
	O6—H6O···O2ⁱⁱ	0.82 (2)	1.94	2.748 (2)	169
	O2'—H2'O···O3^iv	0.82 (2)	1.96	2.775 (3)	175
	O3'—H3'O···O6'^iv	0.82 (2)	1.96	2.740 (2)	160
	O6'—H6'O···O3'ⁱⁱⁱ	0.820 (7)	1.84	2.662 (2)	175

Weak hydrogen bond O3—H3O···O6' was not shown as D···A > 3.0 Å.

Symmetry codes for (I): (i) -x+1, y-1/2, -z+1; (ii) x, y, z-1; (iii) x+1, y, z+1; (iv) -x+2, y-1/2, -z+1. Symmetry codes for (II): (i) -x+2, y-1/2, -z+2; (ii) x+1, y, z+1; (iii) x-1, y, z-1; (iv) x, y, z+1.

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Methyl β-lactoside [methyl β-D-galacto­pyranosyl-(1→4)-β-D-gluco­pyran­oside] monohydrate: a solvomorphism study

Supporting information

Methyl β-lactoside [methyl β-D-galactopyranosyl-(1→4)-β-D-glucopyranoside] monohydrate: a solvomorphism study