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
CCDC reference: 2119923
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean
(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
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-(1
→4)–2-amino-2-deoxy-
α-
D-glucopyranose hydrochloride monohydrate
top
Crystal data top
C12H24NO10+·Cl−·H2O | F(000) = 420 |
Mr = 395.79 | Dx = 1.536 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 4.785 (4) Å | Cell parameters from 1276 reflections |
b = 13.523 (11) Å | θ = 3.0–20.6° |
c = 13.254 (11) Å | µ = 0.28 mm−1 |
β = 93.940 (9)° | T = 273 K |
V = 855.5 (12) Å3 | Plate, colourless |
Z = 2 | 0.08 × 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 optics | Rint = 0.133 |
ω and phi scans | θmax = 27.2°, θmin = 1.5° |
Absorption correction: multi-scan (AXScale; Bruker, 2016) | h = −6→6 |
Tmin = 0.483, Tmax = 0.746 | k = −17→17 |
11475 measured reflections | l = −17→16 |
3787 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.066 | H 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 reflections | Δρmax = 0.44 e Å−3 |
262 parameters | Δρmin = −0.37 e Å−3 |
26 restraints | Absolute structure: Flack x determined using 729 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Cl1 | −0.3280 (4) | 0.75359 (14) | 0.61589 (14) | 0.0286 (5) | |
O1 | −0.1394 (11) | 0.7867 (4) | 0.4014 (4) | 0.0272 (13) | |
H1 | −0.195 (16) | 0.765 (7) | 0.455 (5) | 0.041* | |
O1W | 0.6240 (15) | 1.0329 (4) | 0.4269 (5) | 0.0462 (19) | |
H1WA | 0.71 (2) | 1.021 (8) | 0.488 (6) | 0.069* | |
H1WB | 0.58 (2) | 1.096 (5) | 0.433 (8) | 0.069* | |
O2 | 0.2355 (12) | 0.8551 (4) | 0.1351 (4) | 0.0260 (14) | |
H2 | 0.186 (17) | 0.830 (6) | 0.082 (5) | 0.039* | |
O3 | 0.1487 (12) | 0.4761 (4) | 0.3861 (4) | 0.0341 (14) | |
H3 | 0.18 (2) | 0.416 (4) | 0.387 (7) | 0.051* | |
O4 | 0.2482 (10) | 0.6815 (4) | 0.3919 (4) | 0.0253 (13) | |
O5 | 0.1019 (10) | 0.6413 (4) | 0.1208 (4) | 0.0223 (12) | |
O6 | 0.3161 (10) | 0.4684 (4) | 0.0307 (4) | 0.0263 (12) | |
H6 | 0.175 (14) | 0.446 (6) | 0.055 (6) | 0.039* | |
O7 | 0.3237 (11) | 0.4742 (4) | −0.1838 (4) | 0.0266 (13) | |
H7 | 0.431 (16) | 0.434 (5) | −0.157 (6) | 0.040* | |
O8 | −0.0409 (10) | 0.6292 (4) | −0.2120 (4) | 0.0229 (12) | |
H8 | −0.091 (17) | 0.658 (6) | −0.261 (5) | 0.034* | |
O9 | 0.1635 (11) | 0.9157 (4) | −0.1046 (4) | 0.0255 (13) | |
H9 | 0.321 (13) | 0.933 (6) | −0.082 (6) | 0.038* | |
O10 | 0.1420 (10) | 0.7280 (3) | −0.0250 (4) | 0.0226 (13) | |
N1 | 0.1495 (15) | 0.9460 (5) | 0.3249 (5) | 0.0267 (17) | |
H1A | 0.270 (14) | 0.978 (6) | 0.369 (5) | 0.040* | |
H1B | 0.104 (16) | 0.980 (6) | 0.268 (4) | 0.040* | |
H1C | −0.023 (11) | 0.946 (6) | 0.350 (6) | 0.040* | |
C1 | 0.1489 (16) | 0.7791 (5) | 0.4024 (6) | 0.0250 (18) | |
H1D | 0.231817 | 0.807016 | 0.465797 | 0.030* | |
C2 | 0.2409 (16) | 0.8418 (5) | 0.3134 (6) | 0.0227 (18) | |
H2A | 0.445983 | 0.840893 | 0.315433 | 0.027* | |
C3 | 0.1292 (16) | 0.7968 (5) | 0.2135 (6) | 0.0228 (18) | |
H3A | −0.076034 | 0.799022 | 0.208350 | 0.027* | |
C4 | 0.2270 (15) | 0.6906 (6) | 0.2095 (6) | 0.0224 (18) | |
H4 | 0.431371 | 0.689282 | 0.207687 | 0.027* | |
C5 | 0.1419 (16) | 0.6315 (6) | 0.3013 (5) | 0.0226 (17) | |
H5 | −0.062765 | 0.627481 | 0.300031 | 0.027* | |
C6 | 0.2641 (17) | 0.5292 (6) | 0.3051 (6) | 0.030 (2) | |
H6A | 0.219239 | 0.495436 | 0.241483 | 0.036* | |
H6B | 0.466372 | 0.532736 | 0.316291 | 0.036* | |
C7 | 0.2534 (15) | 0.6458 (6) | 0.0341 (5) | 0.0222 (17) | |
H7A | 0.453220 | 0.655704 | 0.052771 | 0.027* | |
C8 | 0.2081 (16) | 0.5518 (5) | −0.0258 (6) | 0.0217 (17) | |
H8A | 0.007235 | 0.542472 | −0.042707 | 0.026* | |
C9 | 0.3596 (16) | 0.5604 (5) | −0.1230 (5) | 0.0204 (17) | |
H9A | 0.559991 | 0.570369 | −0.105595 | 0.024* | |
C10 | 0.2464 (15) | 0.6483 (6) | −0.1834 (6) | 0.0213 (17) | |
H10 | 0.350340 | 0.656234 | −0.244111 | 0.026* | |
C11 | 0.2853 (15) | 0.7402 (6) | −0.1168 (5) | 0.0220 (17) | |
H11 | 0.485554 | 0.750477 | −0.099407 | 0.026* | |
C12 | 0.1643 (16) | 0.8313 (5) | −0.1692 (6) | 0.0241 (18) | |
H12A | 0.272384 | 0.846504 | −0.226525 | 0.029* | |
H12B | −0.026310 | 0.817433 | −0.194879 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0323 (11) | 0.0230 (11) | 0.0302 (10) | −0.0014 (9) | −0.0006 (8) | 0.0045 (10) |
O1 | 0.027 (3) | 0.023 (3) | 0.032 (4) | 0.002 (2) | 0.004 (3) | 0.004 (3) |
O1W | 0.075 (5) | 0.027 (4) | 0.034 (4) | −0.003 (3) | −0.012 (3) | −0.002 (3) |
O2 | 0.035 (3) | 0.021 (3) | 0.022 (3) | −0.010 (2) | −0.001 (3) | 0.001 (2) |
O3 | 0.056 (4) | 0.016 (3) | 0.030 (3) | −0.003 (3) | 0.004 (3) | 0.007 (3) |
O4 | 0.033 (3) | 0.017 (3) | 0.026 (3) | −0.002 (2) | −0.001 (3) | 0.000 (2) |
O5 | 0.027 (3) | 0.021 (3) | 0.020 (3) | −0.005 (2) | 0.002 (2) | 0.001 (2) |
O6 | 0.025 (3) | 0.021 (3) | 0.033 (3) | 0.001 (3) | 0.005 (2) | 0.006 (3) |
O7 | 0.032 (3) | 0.016 (3) | 0.031 (3) | 0.005 (2) | −0.001 (2) | −0.001 (3) |
O8 | 0.025 (3) | 0.019 (3) | 0.024 (3) | −0.001 (2) | −0.001 (2) | 0.004 (2) |
O9 | 0.026 (3) | 0.019 (3) | 0.032 (3) | 0.000 (2) | 0.001 (3) | −0.003 (3) |
O10 | 0.024 (3) | 0.017 (3) | 0.026 (3) | 0.003 (2) | 0.003 (2) | 0.003 (2) |
N1 | 0.035 (4) | 0.021 (4) | 0.023 (4) | −0.005 (3) | −0.006 (3) | 0.004 (3) |
C1 | 0.030 (5) | 0.018 (4) | 0.026 (4) | −0.002 (3) | −0.001 (3) | 0.003 (3) |
C2 | 0.025 (4) | 0.016 (4) | 0.026 (5) | −0.003 (3) | −0.001 (4) | 0.004 (3) |
C3 | 0.023 (4) | 0.021 (4) | 0.024 (4) | −0.002 (3) | 0.002 (3) | 0.008 (3) |
C4 | 0.020 (4) | 0.019 (4) | 0.029 (5) | −0.004 (3) | 0.000 (3) | 0.000 (4) |
C5 | 0.029 (4) | 0.016 (4) | 0.023 (4) | −0.009 (3) | −0.001 (3) | 0.002 (3) |
C6 | 0.037 (5) | 0.023 (5) | 0.028 (5) | −0.003 (4) | 0.000 (4) | 0.003 (4) |
C7 | 0.023 (4) | 0.021 (4) | 0.023 (4) | 0.001 (3) | 0.002 (3) | 0.004 (4) |
C8 | 0.024 (4) | 0.015 (4) | 0.026 (5) | 0.003 (3) | −0.002 (3) | 0.005 (3) |
C9 | 0.021 (4) | 0.016 (4) | 0.024 (4) | 0.002 (3) | 0.002 (3) | −0.001 (4) |
C10 | 0.020 (4) | 0.019 (4) | 0.025 (4) | −0.002 (3) | 0.004 (3) | 0.003 (3) |
C11 | 0.021 (4) | 0.020 (4) | 0.027 (4) | −0.001 (3) | 0.007 (3) | −0.002 (4) |
C12 | 0.026 (4) | 0.014 (4) | 0.032 (5) | 0.001 (3) | 0.004 (4) | 0.000 (4) |
Geometric parameters (Å, º) top
O1—C1 | 1.382 (9) | N1—H1C | 0.91 (4) |
O1—H1 | 0.83 (5) | C1—C2 | 1.541 (10) |
O1W—H1WA | 0.90 (6) | C1—H1D | 0.9800 |
O1W—H1WB | 0.89 (6) | C2—C3 | 1.521 (10) |
O2—C3 | 1.426 (9) | C2—H2A | 0.9800 |
O2—H2 | 0.80 (5) | C3—C4 | 1.512 (10) |
O3—C6 | 1.434 (10) | C3—H3A | 0.9800 |
O3—H3 | 0.82 (5) | C4—C5 | 1.533 (10) |
O4—C1 | 1.414 (9) | C4—H4 | 0.9800 |
O4—C5 | 1.440 (8) | C5—C6 | 1.502 (11) |
O5—C7 | 1.402 (9) | C5—H5 | 0.9800 |
O5—C4 | 1.445 (9) | C6—H6A | 0.9700 |
O6—C8 | 1.431 (9) | C6—H6B | 0.9700 |
O6—H6 | 0.82 (5) | C7—C8 | 1.507 (10) |
O7—C9 | 1.420 (9) | C7—H7A | 0.9800 |
O7—H7 | 0.81 (5) | C8—C9 | 1.526 (10) |
O8—C10 | 1.424 (9) | C8—H8A | 0.9800 |
O8—H8 | 0.78 (5) | C9—C10 | 1.513 (10) |
O9—C12 | 1.426 (9) | C9—H9A | 0.9800 |
O9—H9 | 0.83 (5) | C10—C11 | 1.528 (10) |
O10—C7 | 1.441 (8) | C10—H10 | 0.9800 |
O10—C11 | 1.447 (8) | C11—C12 | 1.510 (10) |
N1—C2 | 1.486 (10) | C11—H11 | 0.9800 |
N1—H1A | 0.90 (4) | C12—H12A | 0.9700 |
N1—H1B | 0.90 (4) | C12—H12B | 0.9700 |
| | | |
C1—O1—H1 | 110 (6) | C6—C5—H5 | 109.6 |
H1WA—O1W—H1WB | 101 (9) | C4—C5—H5 | 109.6 |
C3—O2—H2 | 108 (6) | O3—C6—C5 | 108.5 (7) |
C6—O3—H3 | 115 (7) | O3—C6—H6A | 110.0 |
C1—O4—C5 | 114.7 (5) | C5—C6—H6A | 110.0 |
C7—O5—C4 | 116.0 (5) | O3—C6—H6B | 110.0 |
C8—O6—H6 | 102 (6) | C5—C6—H6B | 110.0 |
C9—O7—H7 | 105 (6) | H6A—C6—H6B | 108.4 |
C10—O8—H8 | 112 (6) | O5—C7—O10 | 106.7 (5) |
C12—O9—H9 | 114 (6) | O5—C7—C8 | 109.3 (6) |
C7—O10—C11 | 111.5 (5) | O10—C7—C8 | 109.3 (5) |
C2—N1—H1A | 110 (5) | O5—C7—H7A | 110.5 |
C2—N1—H1B | 117 (5) | O10—C7—H7A | 110.5 |
H1A—N1—H1B | 114 (7) | C8—C7—H7A | 110.5 |
C2—N1—H1C | 109 (6) | O6—C8—C7 | 110.8 (6) |
H1A—N1—H1C | 109 (8) | O6—C8—C9 | 109.1 (6) |
H1B—N1—H1C | 97 (7) | C7—C8—C9 | 108.7 (6) |
O1—C1—O4 | 114.2 (6) | O6—C8—H8A | 109.4 |
O1—C1—C2 | 106.8 (6) | C7—C8—H8A | 109.4 |
O4—C1—C2 | 108.8 (6) | C9—C8—H8A | 109.4 |
O1—C1—H1D | 109.0 | O7—C9—C10 | 108.6 (6) |
O4—C1—H1D | 109.0 | O7—C9—C8 | 111.8 (6) |
C2—C1—H1D | 109.0 | C10—C9—C8 | 109.5 (6) |
N1—C2—C3 | 112.4 (6) | O7—C9—H9A | 109.0 |
N1—C2—C1 | 109.9 (6) | C10—C9—H9A | 109.0 |
C3—C2—C1 | 110.2 (6) | C8—C9—H9A | 109.0 |
N1—C2—H2A | 108.1 | O8—C10—C9 | 107.6 (6) |
C3—C2—H2A | 108.1 | O8—C10—C11 | 112.3 (6) |
C1—C2—H2A | 108.1 | C9—C10—C11 | 107.9 (6) |
O2—C3—C4 | 111.9 (7) | O8—C10—H10 | 109.7 |
O2—C3—C2 | 106.9 (6) | C9—C10—H10 | 109.7 |
C4—C3—C2 | 108.6 (6) | C11—C10—H10 | 109.7 |
O2—C3—H3A | 109.8 | O10—C11—C12 | 106.9 (6) |
C4—C3—H3A | 109.8 | O10—C11—C10 | 110.3 (6) |
C2—C3—H3A | 109.8 | C12—C11—C10 | 111.7 (6) |
O5—C4—C3 | 110.8 (6) | O10—C11—H11 | 109.3 |
O5—C4—C5 | 106.7 (6) | C12—C11—H11 | 109.3 |
C3—C4—C5 | 111.6 (6) | C10—C11—H11 | 109.3 |
O5—C4—H4 | 109.3 | O9—C12—C11 | 113.2 (6) |
C3—C4—H4 | 109.3 | O9—C12—H12A | 108.9 |
C5—C4—H4 | 109.3 | C11—C12—H12A | 108.9 |
O4—C5—C6 | 106.8 (6) | O9—C12—H12B | 108.9 |
O4—C5—C4 | 108.6 (6) | C11—C12—H12B | 108.9 |
C6—C5—C4 | 112.5 (7) | H12A—C12—H12B | 107.7 |
O4—C5—H5 | 109.6 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···Cl1 | 0.83 (5) | 2.28 (6) | 3.075 (6) | 163 (9) |
O2—H2···O10 | 0.80 (5) | 1.98 (6) | 2.743 (7) | 159 (8) |
O3—H3···Cl1i | 0.82 (5) | 2.31 (6) | 3.130 (7) | 172 (9) |
O6—H6···O9ii | 0.82 (5) | 1.84 (6) | 2.654 (8) | 171 (9) |
O7—H7···O2iii | 0.81 (5) | 1.92 (6) | 2.697 (8) | 158 (9) |
O8—H8···Cl1iv | 0.78 (5) | 2.32 (6) | 3.080 (5) | 166 (8) |
O9—H9···O6v | 0.83 (5) | 1.88 (5) | 2.707 (8) | 178 (9) |
N1—H1A···O1W | 0.90 (4) | 1.96 (5) | 2.819 (9) | 159 (7) |
N1—H1B···O7vi | 0.90 (4) | 2.26 (7) | 2.862 (8) | 124 (6) |
N1—H1B···O8vi | 0.90 (4) | 2.16 (6) | 2.922 (8) | 142 (7) |
N1—H1C···O1 | 0.91 (4) | 2.34 (8) | 2.787 (9) | 110 (6) |
N1—H1C···O1Wvii | 0.91 (4) | 2.35 (6) | 3.162 (11) | 149 (7) |
O1W—H1WA···O3viii | 0.90 (6) | 1.85 (7) | 2.746 (8) | 170 (10) |
O1W—H1WB···Cl1ix | 0.89 (6) | 2.50 (7) | 3.335 (7) | 156 (9) |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) −x, y−1/2, −z; (iii) −x+1, y−1/2, −z; (iv) x, y, z−1; (v) −x+1, y+1/2, −z; (vi) −x, y+1/2, −z; (vii) x−1, 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-β1→4-Glc link topSugar | Tautomer, conformation | τ | Φ | Ψ | Intramolecular contacts around glycosidic bond (O···H; O···O; O···H—O) |
Gal-β1→4-GlcNH3+Cl-·H2O (I)a | α-pyranose, 4C1 | 116.0 | -95.2 | +90.7 | O10···H—O2 (1.98; 2.743; 159) O5···H-O2 (2.64; 2.964; 106) |
Gal-β1→4-GlcNHCOCH3·H2O (N-acetyllactosamine,
LacNAc·H2O)b | α-pyranose, 4C1b | 116.3 | -88.1 | +97.8 | O10···H-O2 (1.98; 2.787; 139) O5···H—O6 (2.40; 2.868; 122) |
LacNAc/ toad galectinc | α-pyranose, 4C1 | 118.2; 113.6 | -66.9; -67.8 | +132.4; +132.6 | Not reported |
LacNAc calculationsd | α-pyranose, 4C1d | 117.1 | -75 | +135 | O10···H—O2 |
Gal-β1→4-Glc·H2O (α-lactose)e | α-pyranose, 4C1 | 116.9 | -93.4 | +95.9 | O10···H—O2 (2.02; 2.819; 159) O5···H—O2 (2.65; 2.992; 106) |
Gal-β1→4-Glc (β-lactose)f | β-pyranose, 4C1 | 116.5 | -76.3 | +106.4 | O10···H—O2 (n.d.; 2.707; 101) |
Gal-β1→4-GlcNHCOCH3·2H2O
(N-acetyllactosylamine)g | β-pyranose, 4C1 | 117.4 | -89.3 | +81.5 | O10···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, °) topD—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O5 | 0.80 (7) | 2.64 (8) | 2.964 (8) | 106 (6) |
N1—H1B···O2 | 0.90 (6) | 2.55 (7) | 2.855 (9) | 101 (5) |
O7—H7···O6 | 0.81 (8) | 2.63 (8) | 2.847 (8) | 97 (8) |
C2—H2A···O1i | 0.98 | 2.34 | 3.199 (10) | 146 |
C9—H9A···O8i | 0.98 | 2.58 | 3.309 (9) | 132 |
C10—H10···Cl1ii | 0.98 | 2.82 | 3.741 (9) | 157 |
Symmetry codes: (i) x + 1, y, z; (ii) x + 1,
y, z - 1. |