Effect of Neighbors on the Conformational Preferences of Glycosidic Linkages in Glycyrrhizic Acid and Its Mono- and Dideprotonated Forms: X-ray, NMR, and Computational Studies
Tykarska, Ewa; Dutkiewicz, Zbigniew; Baranowski, Daniel; Gdaniec, Zofia; Gdaniec, Maria; Crystal Growth & Design 14 (2014) 5871–; doi:10.1021/cg5010962

data_4512143
_publ_section_title
;
 Effect of Neighbors on the Conformational Preferences of Glycosidic
 Linkages in Glycyrrhizic Acid and Its Mono- and Dideprotonated Forms:
 X-ray, NMR, and Computational Studies
;
_journal_issue                   11
_journal_name_full               'Crystal Growth &amp; Design'
_journal_page_first              5871
_journal_paper_doi               10.1021/cg5010962
_journal_volume                  14
_journal_year                    2014
_chemical_absolute_configuration rm
_chemical_formula_moiety
;
C42 H61 O16, 3.00(C3 H7 N O), 6.53(H2 O), H4 N 
;
_chemical_formula_sum            'C51 H99.06 N4 O25.53'
_chemical_formula_weight         1176.88
_chemical_name_common
;
monoammonium glicyrrhizinate
3.0 DMF 6.53 water solvate
;
_chemical_name_systematic
;
3beta-[O-beta-D-glucopyranuronosyl-
beta-D-glucopyranuronosyloxy]-ll-oxo-
(18betaH)-olean-12-en-30beta-oic 
monoammonium salt
water/DMF solvate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2250(3)
_cell_length_b                   11.4024(3)
_cell_length_c                   53.2811(14)
_cell_measurement_reflns_used    8831
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      73.5892
_cell_measurement_theta_min      2.4857
_cell_volume                     6212.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics
; 
 Mercury CSD 3.3 - new features for the visualization and investigation 
 of crystal structures, C. F. Macrae, I. J. Bruno, J. A. Chisholm, 
 P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, 
 J. van de Streek and P. A. Wood, J. Appl. Cryst., 41, 466-470, 2008.
;
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 (Burla et al.,2005)'
_diffrn_ambient_temperature      130(2)
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -64
_diffrn_reflns_number            16717
_diffrn_reflns_point_group_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.243
_diffrn_reflns_theta_min         3.318
_exptl_absorpt_coefficient_mu    0.844
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2549
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.592
_refine_diff_density_rms         0.090
_refine_ls_abs_structure_details
;
 Flack x determined using 3686 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.21(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     739
_refine_ls_number_reflns         10392
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0951
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1438P)^2^+10.0271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2624
_refine_ls_wR_factor_ref         0.2639
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.812
_reflns_Friedel_fraction_max     0.808
_reflns_number_gt                9983
_reflns_number_total             10392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cg5010962_si_002.cif
_cod_data_source_block           AGA-DMF
_cod_depositor_comments          'Adding full bibliography for 4512143.cif.'
_cod_database_code               4512143
_shelxl_version_number           2014-2
_shelx_res_checksum              35185
_shelx_hkl_checksum              46930