Absolute configuration of naturally occurring glabridin
Simmler, Charlotte; Fronczek, Frank R.; Pauli, Guido F.; Santarsiero, Bernard D.; Acta Crystallographica Section C 69 (2013) 1212–1216; doi:10.1107/S0108270113018842

data_2019243
_publ_section_title
;
 Absolute configuration of naturally occurring glabridin
;
_journal_coeditor_code           LN3162
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1212
_journal_page_last               1216
_journal_paper_doi               10.1107/S0108270113018842
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C20 H20 O4'
_chemical_formula_moiety         'C20 H20 O4'
_chemical_formula_sum            'C20 H20 O4'
_chemical_formula_weight         324.36
_chemical_name_common            glabridin
_chemical_name_systematic
4-[(3<i>R</i>)-8,8-Dimethyl-3,4-dihydro-2<i>H</i>-pyrano[2,3-<i>f</i>]chromen-3-yl]benzene-1,3-diol
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3744(10)
_cell_length_b                   11.961(2)
_cell_length_c                   21.041(3)
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    92(2)
_cell_measurement_theta_max      68.61
_cell_measurement_theta_min      4.21
_cell_volume                     1604.3(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      92(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO CCD aea-detector'
_diffrn_measurement_method       '\f and \w'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            47918
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         68.509
_diffrn_reflns_theta_min         4.202
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.755
_exptl_absorpt_correction_T_max  0.9777
_exptl_absorpt_correction_T_min  0.8952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.133
_refine_ls_abs_structure_details
;
Flack x parameter determined using 1096 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   -0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         2879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0255
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0324P)^2^+0.3419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0599
_refine_ls_wR_factor_ref         0.0614
_reflns_number_gt                2708
_reflns_number_total             2879
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            ln3162.cif
_cod_data_source_block           I
_cod_database_code               2019243
_shelx_hkl_checksum              96254
_shelx_res_checksum              14510
_shelxl_version_number           2.013