#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/51/2015135.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2015135
loop_
_publ_author_name
'Pan, Qingfeng'
'Noll, Bruce C.'
'Serianni, Anthony S.'
_publ_section_title
;
 Methyl 4-O-β-<small>D</small>-galactopyranosyl
 α-<small>D</small>-glucopyranoside (methyl α-lactoside)
;
_journal_coeditor_code           FG1865
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o674
_journal_page_last               o677
_journal_paper_doi               10.1107/S0108270105033706
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C13 H24 O11'
_chemical_formula_moiety         'C13 H24 O11'
_chemical_formula_sum            'C13 H24 O11'
_chemical_formula_weight         356.32
_chemical_name_common            'methyl α-lactoside'
_chemical_name_systematic
;
methyl 4-O-β-D-galactopyranosyl-α-D-glucopyranoside
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.5502(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.6984(3)
_cell_length_b                   5.00610(10)
_cell_length_c                   21.1204(5)
_cell_measurement_reflns_used    8868
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.485
_cell_measurement_theta_min      2.790
_cell_volume                     1543.93(6)
_computing_cell_refinement       'APEX2 and SAINT (Bruker--Nonius, 2004)'
_computing_data_collection       'APEX2 (Bruker--Nonius, 2004)'
_computing_data_reduction        'SAINT and XPREP (Sheldrick, 2003)'
_computing_molecular_graphics    'XP (Sheldrick, 1998)'
_computing_publication_material
'XCIF (Sheldrick, 2001) and enCIFer (Allen et al., 2004)'
_computing_structure_refinement  'XL (Sheldrick, 2001)'
_computing_structure_solution    'XS (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11448
_diffrn_reflns_theta_full        31.50
_diffrn_reflns_theta_max         31.50
_diffrn_reflns_theta_min         0.97
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.238
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2845
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0321
_refine_ls_shift/su_max          0.043
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0697P)²+0.4616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0867
_refine_ls_wR_factor_ref         0.0947
_reflns_number_gt                2758
_reflns_number_total             2845
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1865.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2015135
_cod_database_fobs_code          2015135
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.69499(8) -0.0078(3) 0.18864(6) 0.0097(2) Uani d . 1 . . C
H1 0.6897 0.1776 0.1709 0.012 Uiso calc R 1 . . H
C2 0.77456(8) -0.1537(3) 0.16277(6) 0.0098(2) Uani d . 1 . . C
H2 0.7762 -0.3456 0.1760 0.012 Uiso calc R 1 . . H
C3 0.75616(8) -0.1286(3) 0.08958(6) 0.0096(2) Uani d . 1 . . C
H3 0.7533 0.0668 0.0797 0.012 Uiso calc R 1 . . H
C4 0.66199(9) -0.2462(3) 0.06414(6) 0.0099(2) Uani d . 1 . . C
H4 0.6477 -0.1926 0.0185 0.012 Uiso calc R 1 . . H
C5 0.58682(8) -0.1354(3) 0.10148(6) 0.0101(2) Uani d . 1 . . C
H5 0.5754 0.0560 0.0896 0.012 Uiso calc R 1 . . H
C6 0.49729(9) -0.2886(3) 0.09011(6) 0.0135(2) Uani d . 1 . . C
H6A 0.4798 -0.3125 0.0438 0.016 Uiso calc R 1 . . H
H6B 0.5045 -0.4674 0.1101 0.016 Uiso calc R 1 . . H
C1' 0.61032(9) 0.4679(3) 0.39531(6) 0.0122(2) Uani d . 1 . . C
H1' 0.5912 0.6283 0.4188 0.015 Uiso calc R 1 . . H
C2' 0.54148(9) 0.4242(3) 0.33643(6) 0.0111(2) Uani d . 1 . . C
H2' 0.5422 0.5877 0.3093 0.013 Uiso calc R 1 . . H
C3' 0.57005(9) 0.1893(3) 0.29744(6) 0.0106(2) Uani d . 1 . . C
H3' 0.5680 0.0213 0.3229 0.013 Uiso calc R 1 . . H
C4' 0.66794(9) 0.2367(3) 0.28202(6) 0.0100(2) Uani d . 1 . . C
H4' 0.6683 0.3889 0.2514 0.012 Uiso calc R 1 . . H
C5' 0.73327(9) 0.2988(3) 0.34186(6) 0.0107(2) Uani d . 1 . . C
H5' 0.7423 0.1358 0.3692 0.013 Uiso calc R 1 . . H
C6' 0.82460(9) 0.3937(3) 0.32343(6) 0.0131(2) Uani d . 1 . . C
H6'A 0.8443 0.2735 0.2903 0.016 Uiso calc R 1 . . H
H6'B 0.8173 0.5753 0.3050 0.016 Uiso calc R 1 . . H
C7' 0.64991(14) 0.2851(5) 0.49772(7) 0.0302(4) Uani d . 1 . . C
H7'A 0.7156 0.3133 0.4964 0.045 Uiso calc R 1 . . H
H7'B 0.6406 0.1282 0.5240 0.045 Uiso calc R 1 . . H
H7'C 0.6234 0.4427 0.5161 0.045 Uiso calc R 1 . . H
O1 0.70545(6) 0.0019(2) 0.25464(4) 0.01065(18) Uani d . 1 . . O
O2 0.85833(6) -0.0244(2) 0.18499(5) 0.01283(19) Uani d . 1 . . O
H2A 0.8929 -0.1323 0.2066 0.019 Uiso calc R 1 . . H
O3 0.82630(7) -0.2370(2) 0.05616(4) 0.01276(19) Uani d . 1 . . O
H3A 0.8509 -0.3669 0.0767 0.019 Uiso calc R 1 . . H
O4 0.66407(7) -0.5309(2) 0.06738(5) 0.0138(2) Uani d . 1 . . O
H4A 0.6660 -0.5939 0.0307 0.021 Uiso calc R 1 . . H
O5 0.61288(6) -0.1533(2) 0.16915(4) 0.01033(19) Uani d . 1 . . O
O6 0.42756(7) -0.1416(2) 0.11727(5) 0.0154(2) Uani d . 1 . . O
H6 0.4012 -0.2424 0.1412 0.023 Uiso calc R 1 . . H
O1' 0.60613(8) 0.2429(3) 0.43431(5) 0.0169(2) Uani d . 1 . . O
O2' 0.45171(7) 0.3967(2) 0.35413(5) 0.0145(2) Uani d . 1 . . O
H2'A 0.4450 0.2419 0.3682 0.022 Uiso calc R 1 . . H
O3' 0.50573(7) 0.1704(3) 0.24129(5) 0.0160(2) Uani d . 1 . . O
H3'A 0.5200 0.0416 0.2189 0.024 Uiso calc R 1 . . H
O5' 0.69893(7) 0.5137(2) 0.37744(5) 0.01307(19) Uani d . 1 . . O
O6' 0.89376(7) 0.3986(2) 0.37696(5) 0.0145(2) Uani d . 1 . . O
H6' 0.9160 0.2449 0.3830 0.022 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 O5 107.49(9)
O1 C1 C2 111.95(10)
O5 C1 C2 107.95(11)
O1 C1 H1 109.8
O5 C1 H1 109.8
C2 C1 H1 109.8
O2 C2 C1 109.44(11)
O2 C2 C3 109.85(10)
C1 C2 C3 105.35(10)
O2 C2 H2 110.7
C1 C2 H2 110.7
C3 C2 H2 110.7
O3 C3 C4 110.72(11)
O3 C3 C2 114.33(10)
C4 C3 C2 111.43(10)
O3 C3 H3 106.6
C4 C3 H3 106.6
C2 C3 H3 106.6
O4 C4 C5 110.45(11)
O4 C4 C3 110.53(12)
C5 C4 C3 110.70(11)
O4 C4 H4 108.4
C5 C4 H4 108.4
C3 C4 H4 108.4
O5 C5 C6 104.66(10)
O5 C5 C4 111.26(10)
C6 C5 C4 113.50(11)
O5 C5 H5 109.1
C6 C5 H5 109.1
C4 C5 H5 109.1
O6 C6 C5 108.91(12)
O6 C6 H6A 109.9
C5 C6 H6A 109.9
O6 C6 H6B 109.9
C5 C6 H6B 109.9
H6A C6 H6B 108.3
O1' C1' O5' 112.98(12)
O1' C1' C2' 107.10(12)
O5' C1' C2' 110.51(10)
O1' C1' H1' 108.7
O5' C1' H1' 108.7
C2' C1' H1' 108.7
O2' C2' C3' 112.95(11)
O2' C2' C1' 110.44(10)
C3' C2' C1' 110.70(11)
O2' C2' H2' 107.5
C3' C2' H2' 107.5
C1' C2' H2' 107.5
O3' C3' C2' 107.58(11)
O3' C3' C4' 112.45(10)
C2' C3' C4' 108.64(11)
O3' C3' H3' 109.4
C2' C3' H3' 109.4
C4' C3' H3' 109.4
O1 C4' C3' 111.70(11)
O1 C4' C5' 105.28(10)
C3' C4' C5' 111.88(10)
O1 C4' H4' 109.3
C3' C4' H4' 109.3
C5' C4' H4' 109.3
O5' C5' C6' 105.90(11)
O5' C5' C4' 111.08(11)
C6' C5' C4' 110.02(10)
O5' C5' H5' 109.9
C6' C5' H5' 109.9
C4' C5' H5' 109.9
O6' C6' C5' 111.86(11)
O6' C6' H6'A 109.2
C5' C6' H6'A 109.2
O6' C6' H6'B 109.2
C5' C6' H6'B 109.2
H6'A C6' H6'B 107.9
O1' C7' H7'A 109.5
O1' C7' H7'B 109.5
H7'A C7' H7'B 109.5
O1' C7' H7'C 109.5
H7'A C7' H7'C 109.5
H7'B C7' H7'C 109.5
C1 O1 C4' 115.26(10)
C2 O2 H2A 109.5
C3 O3 H3A 109.5
C4 O4 H4A 109.5
C1 O5 C5 111.98(9)
C6 O6 H6 109.5
C1' O1' C7' 112.66(14)
C2' O2' H2'A 109.5
C3' O3' H3'A 109.5
C1' O5' C5' 114.03(11)
C6' O6' H6' 109.5
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 . 1.3857(14) ?
C1 O5 . 1.4295(16) ?
C1 C2 . 1.5316(17) ?
C1 H1 . 1.0000 ?
C2 O2 . 1.4225(16) ?
C2 C3 . 1.5437(17) ?
C2 H2 . 1.0000 ?
C3 O3 . 1.4219(15) ?
C3 C4 . 1.5432(19) ?
C3 H3 . 1.0000 ?
C4 O4 . 1.4273(18) ?
C4 C5 . 1.5325(18) ?
C4 H4 . 1.0000 ?
C5 O5 . 1.4397(15) ?
C5 C6 . 1.5183(18) ?
C5 H5 . 1.0000 ?
C6 O6 . 1.4333(17) ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C1' O1' . 1.4012(19) ?
C1' O5' . 1.4156(15) ?
C1' C2' . 1.5268(19) ?
C1' H1' . 1.0000 ?
C2' O2' . 1.4185(15) ?
C2' C3' . 1.5221(19) ?
C2' H2' . 1.0000 ?
C3' O3' . 1.4329(16) ?
C3' C4' . 1.5295(17) ?
C3' H3' . 1.0000 ?
C4' O1 . 1.4467(17) ?
C4' C5' . 1.5296(18) ?
C4' H4' . 1.0000 ?
C5' O5' . 1.4364(17) ?
C5' C6' . 1.5159(18) ?
C5' H5' . 1.0000 ?
C6' O6' . 1.4317(16) ?
C6' H6'A . 0.9900 ?
C6' H6'B . 0.9900 ?
C7' O1' . 1.434(2) ?
C7' H7'A . 0.9800 ?
C7' H7'B . 0.9800 ?
C7' H7'C . 0.9800 ?
O2 H2A . 0.8400 ?
O3 H3A . 0.8400 ?
O4 H4A . 0.8400 ?
O6 H6 . 0.8400 ?
O2' H2'A . 0.8400 ?
O3' H3'A . 0.8400 ?
O6' H6' . 0.8400 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2A O3' 3_545 0.84 2.00 2.8026(15) 161 y
O3 H3A O6 3_545 0.84 1.92 2.7469(14) 169 y
O4 H4A O3 4_645 0.84 1.99 2.8243(14) 178 y
O6 H6 O2 3_445 0.84 1.84 2.6619(14) 167 y
O2' H2'A O6' 3_445 0.84 1.89 2.6962(14) 159 y
O6' H6' O2' 3_545 0.84 1.94 2.7138(14) 153 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21181006
