data_2008994
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  1719
_journal_page_last  1721
_publ_section_title
;
 Methyl \b-lactoside (methyl 4-O-\b-D-galactopyranosyl-\b-D-glucopyranoside)
 methanol solvate
;
loop_
_publ_author_name
  'Stenutz, Roland'
  'Shang, Maoyu'
  'Serianni, Anthony S.'
_chemical_name_common
;
 Methyl \b-lactoside
;
_chemical_formula_moiety  'C13 H24 O11 ,CH4 O'
_chemical_formula_sum  'C14 H28 O12'
_chemical_formula_weight  388.36
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  4.6590(10)
_cell_length_b  25.117(2)
_cell_length_c  7.7580(10)
_cell_angle_alpha  90.00
_cell_angle_beta  105.510(10)
_cell_angle_gamma  90.00
_cell_volume  874.9(2)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.474
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs  .0301
_refine_ls_wR_factor_obs  .0781
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  C1  .6854(6) 1.00359(10)  .4609(3)  .0313(5) Uani d . 1 . C
  H1  .4742(6) 1.00467(10)  .4586(3)  .038 Uiso calc R 1 . H
  O1  .7464(5) 1.04114(7)  .3450(2)  .0427(4) Uani d . 1 . O
  C2  .7650(5)  .94972(10)  .3985(3)  .0285(5) Uani d . 1 . C
  H2  .9674(5)  .95214(10)  .3844(3)  .034 Uiso calc R 1 . H
  O2  .5696(5)  .93862(8)  .2280(2)  .0422(5) Uani d . 1 . O
  H2O  .484(7)  .9103(8)  .2319(15)  .063 Uiso calc R 1 . H
  C3  .7623(5)  .90559(9)  .5320(3)  .0284(5) Uani d . 1 . C
  H3  .5550(5)  .89620(9)  .5240(3)  .034 Uiso calc R 1 . H
  O3  .9027(4)  .86130(7)  .4746(2)  .0375(4) Uani d . 1 . O
  H3O  .854(7)  .8339(2)  .517(4)  .056 Uiso calc R 1 . H
  C4  .9153(5)  .92220(9)  .7246(3)  .0252(5) Uani d . 1 . C
  H4 1.1316(5)  .92265(9)  .7426(3)  .030 Uiso calc R 1 . H
  O4  .8423(4)  .88757(6)  .8542(2)  .0281(3) Uani d . 1 . O
  C5  .8097(5)  .97748(9)  .7634(3)  .0279(5) Uani d . 1 . C
  H5  .5945(5)  .97606(9)  .7493(3)  .033 Uiso calc R 1 . H
  O5  .8659(4) 1.01404(6)  .6352(2)  .0316(4) Uani d . 1 . O
  C6  .9595(6)  .99823(10)  .9480(3)  .0314(5) Uani d . 1 . C
  H6A  .8640(6) 1.03106(10)  .9685(3)  .038 Uiso calc R 1 . H
  H6B  .9372(6)  .97248(10) 1.0367(3)  .038 Uiso calc R 1 . H
  O6 1.2680(4) 1.00779(8)  .9678(2)  .0364(4) Uani d . 1 . O
  H6O 1.3673(4)  .9906(11) 1.053(3)  .055 Uiso calc R 1 . H
  C7  .6129(10) 1.09146(13)  .3550(4)  .0633(10) Uani d . 1 . C
  H7A  .6393(10) 1.11392(13)  .2603(4)  .095 Uiso calc R 1 . H
  H7B  .7050(10) 1.10772(13)  .4683(4)  .095 Uiso calc R 1 . H
  H7C  .4040(10) 1.08676(13)  .3432(4)  .095 Uiso calc R 1 . H
  C1'  .9913(5)  .83924(9)  .8833(3)  .0255(5) Uani d . 1 . C
  H1' 1.1917(5)  .84306(9)  .8670(3)  .031 Uiso calc R 1 . H
  C2' 1.0092(5)  .81897(9) 1.0715(3)  .0248(5) Uani d . 1 . C
  H2'  .8080(5)  .81598(9) 1.0873(3)  .030 Uiso calc R 1 . H
  O2' 1.1795(4)  .85454(7) 1.2001(2)  .0369(4) Uani d . 1 . O
  H2O' 1.108(5)  .8564(12) 1.286(2)  .055 Uiso calc R 1 . H
  C3' 1.1569(5)  .76405(9) 1.0925(3)  .0264(5) Uani d . 1 . C
  H3' 1.3574(5)  .76916(9) 1.0776(3)  .032 Uiso calc R 1 . H
  O3' 1.1935(4)  .74226(8) 1.2662(2)  .0345(4) Uani d . 1 . O
  H3O' 1.040(3)  .7465(14) 1.297(2)  .052 Uiso calc R 1 . H
  C4'  .9980(5)  .72553(9)  .9468(3)  .0257(5) Uani d . 1 . C
  H4' 1.1149(5)  .69272(9)  .9554(3)  .031 Uiso calc R 1 . H
  O4'  .7099(4)  .71325(7)  .9658(2)  .0326(4) Uani d . 1 . O
  H4O'  .705(2)  .6819(4)  .995(5)  .049 Uiso calc R 1 . H
  C5'  .9711(5)  .75163(9)  .7663(3)  .0257(4) Uani d . 1 . C
  H5' 1.1707(5)  .75727(9)  .7506(3)  .031 Uiso calc R 1 . H
  O5'  .8230(4)  .80191(6)  .7581(2)  .0268(4) Uani d . 1 . O
  C6'  .7890(6)  .71917(10)  .6115(3)  .0326(5) Uani d . 1 . C
  H6A'  .8839(6)  .68496(10)  .6078(3)  .039 Uiso calc R 1 . H
  H6B'  .5921(6)  .71287(10)  .6270(3)  .039 Uiso calc R 1 . H
  O6'  .7648(4)  .74709(8)  .4482(2)  .0366(4) Uani d . 1 . O
  H6O'  .5907(13)  .7470(12)  .388(2)  .055 Uiso calc R 1 . H
  O11 1.3505(8) 1.11380(9)  .9217(3)  .0688(7) Uani d . 1 . O
  H11O 1.348(13)  1.08280(12)  .954(3)  .103 Uiso calc R 1 . H
  C11 1.3939(10) 1.1150(2)  .7511(5)  .0618(9) Uani d . 1 . C
  H11A 1.2879(10) 1.0861(2)  .6817(5)  .093 Uiso calc R 1 . H
  H11B 1.6025(10) 1.1117(2)  .7598(5)  .093 Uiso calc R 1 . H
  H11C 1.3211(10) 1.1481(2)  .6942(5)  .093 Uiso calc R 1 . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  C1  .0370(12)  .0292(12)  .0245(11)  -.0008(10)  .0029(9)  .0039(9)
  O1  .0664(12)  .0289(9)  .0314(9)  -.0006(9)  .0108(8)  .0085(8)
  C2  .0327(12)  .0296(12)  .0214(11)  -.0044(9)  .0042(9)  .0031(9)
  O2  .0568(12)  .0351(10)  .0259(8)  -.0131(8)  -.0040(8)  .0055(7)
  C3  .0344(11)  .0265(12)  .0248(11)  -.0038(9)  .0085(9)  -.0010(9)
  O3  .0638(12)  .0242(8)  .0290(8)  .0001(8)  .0205(8)  .0000(7)
  C4  .0298(10)  .0248(11)  .0214(10)  -.0023(9)  .0075(8)  .0029(9)
  O4  .0368(8)  .0245(8)  .0252(7)  .0015(7)  .0119(6)  .0036(6)
  C5  .0325(11)  .0238(11)  .0275(11)  -.0004(9)  .0083(9)  .0025(9)
  O5  .0429(9)  .0239(8)  .0249(8)  -.0041(7)  .0039(7)  .0033(6)
  C6  .0395(13)  .0283(12)  .0267(11)  -.0001(9)  .0096(10)  -.0036(9)
  O6  .0373(9)  .0350(9)  .0317(9)  -.0044(7)  .0002(7)  .0060(7)
  C7  .106(3)  .033(2)  .047(2)  .010(2)  .012(2)  .0095(13)
  C1'  .0294(10)  .0255(11)  .0215(10)  -.0012(9)  .0065(9)  .0017(8)
  C2'  .0277(10)  .0262(12)  .0206(10)  -.0038(9)  .0067(8)  -.0009(8)
  O2'  .0455(10)  .0400(10)  .0243(8)  -.0145(8)  .0076(7)  -.0069(7)
  C3'  .0241(10)  .0333(12)  .0212(10)  .0020(9)  .0051(8)  .0053(9)
  O3'  .0335(9)  .0450(10)  .0237(8)  .0052(7)  .0057(7)  .0094(7)
  C4'  .0235(10)  .0254(11)  .0283(11)  .0039(9)  .0072(8)  .0020(9)
  O4'  .0304(8)  .0283(9)  .0400(9)  -.0014(7)  .0108(7)  .0054(7)
  C5'  .0271(10)  .0269(11)  .0224(10)  .0025(9)  .0057(8)  -.0023(9)
  O5'  .0315(8)  .0241(8)  .0217(7)  .0020(6)  .0015(6)  .0008(6)
  C6'  .0385(12)  .0299(12)  .0263(11)  -.0002(10)  .0034(9)  -.0014(10)
  O6'  .0364(9)  .0505(11)  .0205(8)  -.0035(8)  .0033(7)  -.0014(7)
  O11  .127(2)  .0284(10)  .0644(15)  -.0018(13)  .048(2)  -.0032(10)
  C11  .094(3)  .042(2)  .051(2)  -.002(2)  .022(2)  .0034(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C1 O1 . 1.384(3) yes
  C1 O5 . 1.413(3) yes
  C1 C2 . 1.516(3) ?
  C1 H1 .  .98 ?
  O1 C7 . 1.420(4) yes
  C2 O2 . 1.419(3) ?
  C2 C3 . 1.519(3) ?
  C2 H2 .  .98 ?
  O2 H2O .  .82 ?
  C3 O3 . 1.421(3) ?
  C3 C4 . 1.532(3) ?
  C3 H3 .  .98 ?
  O3 H3O .  .82 ?
  C4 O4 . 1.437(3) yes
  C4 C5 . 1.529(3) ?
  C4 H4 .  .98 ?
  O4 C1' . 1.387(3) yes
  C5 O5 . 1.429(3) ?
  C5 C6 . 1.509(3) ?
  C5 H5 .  .98 ?
  C6 O6 . 1.425(3) ?
  C6 H6A .  .97 ?
  C6 H6B .  .97 ?
  O6 H6O .  .82 ?
  C7 H7A .  .96 ?
  C7 H7B .  .96 ?
  C7 H7C .  .96 ?
  C1' O5' . 1.425(3) yes
  C1' C2' . 1.528(3) ?
  C1' H1' .  .98 ?
  C2' O2' . 1.414(3) ?
  C2' C3' . 1.531(3) ?
  C2' H2' .  .98 ?
  O2' H2O' .  .82 ?
  C3' O3' . 1.422(2) ?
  C3' C4' . 1.521(3) ?
  C3' H3' .  .98 ?
  O3' H3O' .  .82 ?
  C4' O4' . 1.423(3) ?
  C4' C5' . 1.521(3) ?
  C4' H4' .  .98 ?
  O4' H4O' .  .82 ?
  C5' O5' . 1.432(3) ?
  C5' C6' . 1.511(3) ?
  C5' H5' .  .98 ?
  C6' O6' . 1.426(3) ?
  C6' H6A' .  .97 ?
  C6' H6B' .  .97 ?
  O6' H6O' .  .82 ?
  O11 C11 . 1.391(4) ?
  O11 H11O .  .82 ?
  C11 H11A .  .96 ?
  C11 H11B .  .96 ?
  C11 H11C .  .96 ?