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The title compound, C12H24NO10+·Cl·H2O, (I), crystallizes in the monoclinic space group P21 and exists as a monohydrate of a monosubstituted ammonium chloride salt, with the reducing carbohydrate portion existing exclusively as the α-pyran­ose tautomer. The glycosidic bond geometry in (I) is stabilized by an intra­molecular hydrogen bond and is close to that found in crystalline α-lactose. All heteroatoms except gluco­pyran­ose ring O4 participate in an extensive hydrogen-bonding network, which propagates in all directions in the crystal structure of (I).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S241431462200061X/gg4007sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S241431462200061X/gg4007Isup2.hkl
Contains datablock I

CCDC reference: 2119923

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.066
  • wR factor = 0.131
  • Data-to-parameter ratio = 14.5

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds ............... 0.0111 Ang.
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.12 Rint given 0.133 PLAT414_ALERT_2_C Short Intra D-H..H-X H6 ..H8A . 1.97 Ang. x,y,z = 1_555 Check PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite 21 Note PLAT020_ALERT_3_G The Value of Rint is Greater Than 0.12 ......... 0.133 Report PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records 3 Report PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K) 273 Check PLAT200_ALERT_1_G Reported _diffrn_ambient_temperature ..... (K) 273 Check PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels .......... 2 Note PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd. # 2 Note Cl PLAT791_ALERT_4_G Model has Chirality at C1 (Sohnke SpGr) S Verify PLAT791_ALERT_4_G Model has Chirality at C2 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C3 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C4 (Sohnke SpGr) S Verify PLAT791_ALERT_4_G Model has Chirality at C5 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C7 (Sohnke SpGr) S Verify PLAT791_ALERT_4_G Model has Chirality at C8 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C9 (Sohnke SpGr) S Verify PLAT791_ALERT_4_G Model has Chirality at C10 (Sohnke SpGr) R Verify PLAT791_ALERT_4_G Model has Chirality at C11 (Sohnke SpGr) R Verify PLAT860_ALERT_3_G Number of Least-Squares Restraints ............. 26 Note PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L= 0.600 13 Note
0 ALERT level A = Most likely a serious problem - resolve or explain 1 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 19 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 14 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: APEX3 and SAINT (Bruker, 2016); data reduction: APEX3 and SAINT (Bruker, 2016); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017/1 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

β-D-Galactopyranosyl-(14)–2-amino-2-deoxy-α-D-glucopyranose hydrochloride monohydrate top
Crystal data top
C12H24NO10+·Cl·H2OF(000) = 420
Mr = 395.79Dx = 1.536 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 4.785 (4) ÅCell parameters from 1276 reflections
b = 13.523 (11) Åθ = 3.0–20.6°
c = 13.254 (11) ŵ = 0.28 mm1
β = 93.940 (9)°T = 273 K
V = 855.5 (12) Å3Plate, colourless
Z = 20.08 × 0.05 × 0.01 mm
Data collection top
Bruker APEXII area detector
diffractometer
2216 reflections with I > 2σ(I)
Radiation source: Sealed Source Mo with TRIUMPH opticsRint = 0.133
ω and phi scansθmax = 27.2°, θmin = 1.5°
Absorption correction: multi-scan
(AXScale; Bruker, 2016)
h = 66
Tmin = 0.483, Tmax = 0.746k = 1717
11475 measured reflectionsl = 1716
3787 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0475P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3787 reflectionsΔρmax = 0.44 e Å3
262 parametersΔρmin = 0.37 e Å3
26 restraintsAbsolute structure: Flack x determined using 729 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (11)
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.

Refinement. Hydroxy and nitrogen-bound H atoms were located in difference-Fourier analyses and were allowed to refine fully. Other H atoms were placed at calculated positions and treated as riding. All chemically equivalent N—H and O—H bond distances were restrained to be equal within 0.05 Å.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.3280 (4)0.75359 (14)0.61589 (14)0.0286 (5)
O10.1394 (11)0.7867 (4)0.4014 (4)0.0272 (13)
H10.195 (16)0.765 (7)0.455 (5)0.041*
O1W0.6240 (15)1.0329 (4)0.4269 (5)0.0462 (19)
H1WA0.71 (2)1.021 (8)0.488 (6)0.069*
H1WB0.58 (2)1.096 (5)0.433 (8)0.069*
O20.2355 (12)0.8551 (4)0.1351 (4)0.0260 (14)
H20.186 (17)0.830 (6)0.082 (5)0.039*
O30.1487 (12)0.4761 (4)0.3861 (4)0.0341 (14)
H30.18 (2)0.416 (4)0.387 (7)0.051*
O40.2482 (10)0.6815 (4)0.3919 (4)0.0253 (13)
O50.1019 (10)0.6413 (4)0.1208 (4)0.0223 (12)
O60.3161 (10)0.4684 (4)0.0307 (4)0.0263 (12)
H60.175 (14)0.446 (6)0.055 (6)0.039*
O70.3237 (11)0.4742 (4)0.1838 (4)0.0266 (13)
H70.431 (16)0.434 (5)0.157 (6)0.040*
O80.0409 (10)0.6292 (4)0.2120 (4)0.0229 (12)
H80.091 (17)0.658 (6)0.261 (5)0.034*
O90.1635 (11)0.9157 (4)0.1046 (4)0.0255 (13)
H90.321 (13)0.933 (6)0.082 (6)0.038*
O100.1420 (10)0.7280 (3)0.0250 (4)0.0226 (13)
N10.1495 (15)0.9460 (5)0.3249 (5)0.0267 (17)
H1A0.270 (14)0.978 (6)0.369 (5)0.040*
H1B0.104 (16)0.980 (6)0.268 (4)0.040*
H1C0.023 (11)0.946 (6)0.350 (6)0.040*
C10.1489 (16)0.7791 (5)0.4024 (6)0.0250 (18)
H1D0.2318170.8070160.4657970.030*
C20.2409 (16)0.8418 (5)0.3134 (6)0.0227 (18)
H2A0.4459830.8408930.3154330.027*
C30.1292 (16)0.7968 (5)0.2135 (6)0.0228 (18)
H3A0.0760340.7990220.2083500.027*
C40.2270 (15)0.6906 (6)0.2095 (6)0.0224 (18)
H40.4313710.6892820.2076870.027*
C50.1419 (16)0.6315 (6)0.3013 (5)0.0226 (17)
H50.0627650.6274810.3000310.027*
C60.2641 (17)0.5292 (6)0.3051 (6)0.030 (2)
H6A0.2192390.4954360.2414830.036*
H6B0.4663720.5327360.3162910.036*
C70.2534 (15)0.6458 (6)0.0341 (5)0.0222 (17)
H7A0.4532200.6557040.0527710.027*
C80.2081 (16)0.5518 (5)0.0258 (6)0.0217 (17)
H8A0.0072350.5424720.0427070.026*
C90.3596 (16)0.5604 (5)0.1230 (5)0.0204 (17)
H9A0.5599910.5703690.1055950.024*
C100.2464 (15)0.6483 (6)0.1834 (6)0.0213 (17)
H100.3503400.6562340.2441110.026*
C110.2853 (15)0.7402 (6)0.1168 (5)0.0220 (17)
H110.4855540.7504770.0994070.026*
C120.1643 (16)0.8313 (5)0.1692 (6)0.0241 (18)
H12A0.2723840.8465040.2265250.029*
H12B0.0263100.8174330.1948790.029*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0323 (11)0.0230 (11)0.0302 (10)0.0014 (9)0.0006 (8)0.0045 (10)
O10.027 (3)0.023 (3)0.032 (4)0.002 (2)0.004 (3)0.004 (3)
O1W0.075 (5)0.027 (4)0.034 (4)0.003 (3)0.012 (3)0.002 (3)
O20.035 (3)0.021 (3)0.022 (3)0.010 (2)0.001 (3)0.001 (2)
O30.056 (4)0.016 (3)0.030 (3)0.003 (3)0.004 (3)0.007 (3)
O40.033 (3)0.017 (3)0.026 (3)0.002 (2)0.001 (3)0.000 (2)
O50.027 (3)0.021 (3)0.020 (3)0.005 (2)0.002 (2)0.001 (2)
O60.025 (3)0.021 (3)0.033 (3)0.001 (3)0.005 (2)0.006 (3)
O70.032 (3)0.016 (3)0.031 (3)0.005 (2)0.001 (2)0.001 (3)
O80.025 (3)0.019 (3)0.024 (3)0.001 (2)0.001 (2)0.004 (2)
O90.026 (3)0.019 (3)0.032 (3)0.000 (2)0.001 (3)0.003 (3)
O100.024 (3)0.017 (3)0.026 (3)0.003 (2)0.003 (2)0.003 (2)
N10.035 (4)0.021 (4)0.023 (4)0.005 (3)0.006 (3)0.004 (3)
C10.030 (5)0.018 (4)0.026 (4)0.002 (3)0.001 (3)0.003 (3)
C20.025 (4)0.016 (4)0.026 (5)0.003 (3)0.001 (4)0.004 (3)
C30.023 (4)0.021 (4)0.024 (4)0.002 (3)0.002 (3)0.008 (3)
C40.020 (4)0.019 (4)0.029 (5)0.004 (3)0.000 (3)0.000 (4)
C50.029 (4)0.016 (4)0.023 (4)0.009 (3)0.001 (3)0.002 (3)
C60.037 (5)0.023 (5)0.028 (5)0.003 (4)0.000 (4)0.003 (4)
C70.023 (4)0.021 (4)0.023 (4)0.001 (3)0.002 (3)0.004 (4)
C80.024 (4)0.015 (4)0.026 (5)0.003 (3)0.002 (3)0.005 (3)
C90.021 (4)0.016 (4)0.024 (4)0.002 (3)0.002 (3)0.001 (4)
C100.020 (4)0.019 (4)0.025 (4)0.002 (3)0.004 (3)0.003 (3)
C110.021 (4)0.020 (4)0.027 (4)0.001 (3)0.007 (3)0.002 (4)
C120.026 (4)0.014 (4)0.032 (5)0.001 (3)0.004 (4)0.000 (4)
Geometric parameters (Å, º) top
O1—C11.382 (9)N1—H1C0.91 (4)
O1—H10.83 (5)C1—C21.541 (10)
O1W—H1WA0.90 (6)C1—H1D0.9800
O1W—H1WB0.89 (6)C2—C31.521 (10)
O2—C31.426 (9)C2—H2A0.9800
O2—H20.80 (5)C3—C41.512 (10)
O3—C61.434 (10)C3—H3A0.9800
O3—H30.82 (5)C4—C51.533 (10)
O4—C11.414 (9)C4—H40.9800
O4—C51.440 (8)C5—C61.502 (11)
O5—C71.402 (9)C5—H50.9800
O5—C41.445 (9)C6—H6A0.9700
O6—C81.431 (9)C6—H6B0.9700
O6—H60.82 (5)C7—C81.507 (10)
O7—C91.420 (9)C7—H7A0.9800
O7—H70.81 (5)C8—C91.526 (10)
O8—C101.424 (9)C8—H8A0.9800
O8—H80.78 (5)C9—C101.513 (10)
O9—C121.426 (9)C9—H9A0.9800
O9—H90.83 (5)C10—C111.528 (10)
O10—C71.441 (8)C10—H100.9800
O10—C111.447 (8)C11—C121.510 (10)
N1—C21.486 (10)C11—H110.9800
N1—H1A0.90 (4)C12—H12A0.9700
N1—H1B0.90 (4)C12—H12B0.9700
C1—O1—H1110 (6)C6—C5—H5109.6
H1WA—O1W—H1WB101 (9)C4—C5—H5109.6
C3—O2—H2108 (6)O3—C6—C5108.5 (7)
C6—O3—H3115 (7)O3—C6—H6A110.0
C1—O4—C5114.7 (5)C5—C6—H6A110.0
C7—O5—C4116.0 (5)O3—C6—H6B110.0
C8—O6—H6102 (6)C5—C6—H6B110.0
C9—O7—H7105 (6)H6A—C6—H6B108.4
C10—O8—H8112 (6)O5—C7—O10106.7 (5)
C12—O9—H9114 (6)O5—C7—C8109.3 (6)
C7—O10—C11111.5 (5)O10—C7—C8109.3 (5)
C2—N1—H1A110 (5)O5—C7—H7A110.5
C2—N1—H1B117 (5)O10—C7—H7A110.5
H1A—N1—H1B114 (7)C8—C7—H7A110.5
C2—N1—H1C109 (6)O6—C8—C7110.8 (6)
H1A—N1—H1C109 (8)O6—C8—C9109.1 (6)
H1B—N1—H1C97 (7)C7—C8—C9108.7 (6)
O1—C1—O4114.2 (6)O6—C8—H8A109.4
O1—C1—C2106.8 (6)C7—C8—H8A109.4
O4—C1—C2108.8 (6)C9—C8—H8A109.4
O1—C1—H1D109.0O7—C9—C10108.6 (6)
O4—C1—H1D109.0O7—C9—C8111.8 (6)
C2—C1—H1D109.0C10—C9—C8109.5 (6)
N1—C2—C3112.4 (6)O7—C9—H9A109.0
N1—C2—C1109.9 (6)C10—C9—H9A109.0
C3—C2—C1110.2 (6)C8—C9—H9A109.0
N1—C2—H2A108.1O8—C10—C9107.6 (6)
C3—C2—H2A108.1O8—C10—C11112.3 (6)
C1—C2—H2A108.1C9—C10—C11107.9 (6)
O2—C3—C4111.9 (7)O8—C10—H10109.7
O2—C3—C2106.9 (6)C9—C10—H10109.7
C4—C3—C2108.6 (6)C11—C10—H10109.7
O2—C3—H3A109.8O10—C11—C12106.9 (6)
C4—C3—H3A109.8O10—C11—C10110.3 (6)
C2—C3—H3A109.8C12—C11—C10111.7 (6)
O5—C4—C3110.8 (6)O10—C11—H11109.3
O5—C4—C5106.7 (6)C12—C11—H11109.3
C3—C4—C5111.6 (6)C10—C11—H11109.3
O5—C4—H4109.3O9—C12—C11113.2 (6)
C3—C4—H4109.3O9—C12—H12A108.9
C5—C4—H4109.3C11—C12—H12A108.9
O4—C5—C6106.8 (6)O9—C12—H12B108.9
O4—C5—C4108.6 (6)C11—C12—H12B108.9
C6—C5—C4112.5 (7)H12A—C12—H12B107.7
O4—C5—H5109.6
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···Cl10.83 (5)2.28 (6)3.075 (6)163 (9)
O2—H2···O100.80 (5)1.98 (6)2.743 (7)159 (8)
O3—H3···Cl1i0.82 (5)2.31 (6)3.130 (7)172 (9)
O6—H6···O9ii0.82 (5)1.84 (6)2.654 (8)171 (9)
O7—H7···O2iii0.81 (5)1.92 (6)2.697 (8)158 (9)
O8—H8···Cl1iv0.78 (5)2.32 (6)3.080 (5)166 (8)
O9—H9···O6v0.83 (5)1.88 (5)2.707 (8)178 (9)
N1—H1A···O1W0.90 (4)1.96 (5)2.819 (9)159 (7)
N1—H1B···O7vi0.90 (4)2.26 (7)2.862 (8)124 (6)
N1—H1B···O8vi0.90 (4)2.16 (6)2.922 (8)142 (7)
N1—H1C···O10.91 (4)2.34 (8)2.787 (9)110 (6)
N1—H1C···O1Wvii0.91 (4)2.35 (6)3.162 (11)149 (7)
O1W—H1WA···O3viii0.90 (6)1.85 (7)2.746 (8)170 (10)
O1W—H1WB···Cl1ix0.89 (6)2.50 (7)3.335 (7)156 (9)
Symmetry codes: (i) x, y1/2, z+1; (ii) x, y1/2, z; (iii) x+1, y1/2, z; (iv) x, y, z1; (v) x+1, y+1/2, z; (vi) x, y+1/2, z; (vii) x1, y, z; (viii) x+1, y+1/2, z+1; (ix) x, y+1/2, z+1.
Conformational features (Å, °) of the glycosidic bond in (I) and related disaccharide structures with the Gal-β14-Glc link top
SugarTautomer, conformationτΦΨIntramolecular contacts around glycosidic bond (O···H; O···O; O···H—O)
Gal-β14-GlcNH3+Cl-·H2O (I)aα-pyranose, 4C1116.0-95.2+90.7O10···H—O2 (1.98; 2.743; 159) O5···H-O2 (2.64; 2.964; 106)
Gal-β14-GlcNHCOCH3·H2O (N-acetyllactosamine, LacNAc·H2O)bα-pyranose, 4C1b116.3-88.1+97.8O10···H-O2 (1.98; 2.787; 139) O5···H—O6 (2.40; 2.868; 122)
LacNAc/ toad galectincα-pyranose, 4C1118.2; 113.6-66.9; -67.8+132.4; +132.6Not reported
LacNAc calculationsdα-pyranose, 4C1d117.1-75+135O10···H—O2
Gal-β14-Glc·H2O (α-lactose)eα-pyranose, 4C1116.9-93.4+95.9O10···H—O2 (2.02; 2.819; 159) O5···H—O2 (2.65; 2.992; 106)
Gal-β14-Glc (β-lactose)fβ-pyranose, 4C1116.5-76.3+106.4O10···H—O2 (n.d.; 2.707; 101)
Gal-β14-GlcNHCOCH3·2H2O (N-acetyllactosylamine)gβ-pyranose, 4C1117.4-89.3+81.5O10···H—O2 (2.06; 2.767; 144) O9···H—O2 (2.45; 3.126; 141)
Notes: (a) This work; (b) Longchambon et al. (1981); (c) Bianchet et al. (2000); (d) Imberty et al. (1991); (e) Smith et al. (2005); (f) Hirotsu & Shimada (1974); (g) Lakshmanan et al. (2001).
Additional D—H···A contacts (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O50.80 (7)2.64 (8)2.964 (8)106 (6)
N1—H1B···O20.90 (6)2.55 (7)2.855 (9)101 (5)
O7—H7···O60.81 (8)2.63 (8)2.847 (8)97 (8)
C2—H2A···O1i0.982.343.199 (10)146
C9—H9A···O8i0.982.583.309 (9)132
C10—H10···Cl1ii0.982.823.741 (9)157
Symmetry codes: (i) x + 1, y, z; (ii) x + 1, y, z - 1.
 

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