#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/92/2019243.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_2019243
loop_
_publ_author_name
'Simmler, Charlotte'
'Fronczek, Frank R.'
'Pauli, Guido F.'
'Santarsiero, Bernard D.'
_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-[(3R)-8,8-Dimethyl-3,4-dihydro-2H-pyrano[2,3-f]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       'φ and ω'
_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 et al., 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/[σ²(Fo²)+(0.0324P)²+0.3419P] where P=(Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            ln3162.cif
_cod_data_source_block           I
_cod_database_code               2019243
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2.013
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_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_occupancy
C C1A 0.5348(3) 0.41798(14) 0.46350(8) 0.0178(4) Uani d 1
C C2A 0.3549(3) 0.34964(15) 0.46223(8) 0.0179(4) Uani d 1
O O2A 0.2046(2) 0.37100(11) 0.50754(6) 0.0235(3) Uani d 1
H H2A 0.119(4) 0.317(2) 0.5091(11) 0.035 Uiso d 1
C C3A 0.3301(3) 0.26477(15) 0.41751(9) 0.0183(4) Uani d 1
H H3A 0.209(4) 0.2201(17) 0.4177(9) 0.022 Uiso d 1
C C4A 0.4854(3) 0.24727(15) 0.37179(8) 0.0189(4) Uani d 1
O O4A 0.4515(2) 0.16339(11) 0.32871(6) 0.0243(3) Uani d 1
H H4A 0.550(4) 0.161(2) 0.3009(11) 0.036 Uiso d 1
C C5A 0.6645(3) 0.31343(16) 0.37152(9) 0.0211(4) Uani d 1
H H5A 0.774(4) 0.3022(18) 0.3398(9) 0.025 Uiso d 1
C C6A 0.6871(3) 0.39709(15) 0.41730(9) 0.0203(4) Uani d 1
H H6A 0.814(4) 0.4403(17) 0.4177(10) 0.024 Uiso d 1
O O1 0.4235(2) 0.69199(10) 0.54946(6) 0.0214(3) Uani d 1
C C2 0.4297(3) 0.61178(16) 0.49751(9) 0.0203(4) Uani d 1
H H21 0.487(4) 0.6480(17) 0.4591(10) 0.024 Uiso d 1
H H22 0.280(4) 0.5939(18) 0.4886(10) 0.024 Uiso d 1
C C3 0.5547(3) 0.50714(15) 0.51435(8) 0.0182(4) Uani d 1
H H3 0.493(3) 0.4770(17) 0.5531(10) 0.022 Uiso d 1
C C4 0.7802(3) 0.54459(15) 0.52873(9) 0.0205(4) Uani d 1
H H41 0.865(3) 0.4797(19) 0.5424(10) 0.025 Uiso d 1
H H42 0.838(3) 0.5780(18) 0.4902(10) 0.025 Uiso d 1
C C5 0.9300(3) 0.63739(16) 0.62720(9) 0.0217(4) Uani d 1
H H5 1.051(4) 0.5890(18) 0.6218(9) 0.026 Uiso d 1
C C6 0.9161(3) 0.70976(16) 0.67885(9) 0.0217(4) Uani d 1
H H6 1.029(4) 0.7158(18) 0.7106(9) 0.026 Uiso d 1
C C7 0.7389(3) 0.77578(14) 0.68483(8) 0.0180(4) Uani d 1
C C8 0.5746(3) 0.77139(15) 0.64067(8) 0.0177(4) Uani d 1
C C9 0.5938(3) 0.69660(15) 0.58945(8) 0.0176(4) Uani d 1
C C10 0.7716(3) 0.62927(14) 0.58174(8) 0.0183(4) Uani d 1
O O1B 0.7192(2) 0.84092(10) 0.73914(6) 0.0208(3) Uani d 1
C C2B 0.5885(3) 0.94209(15) 0.73530(9) 0.0205(4) Uani d 1
C C3B 0.3909(3) 0.91720(16) 0.69821(9) 0.0219(4) Uani d 1
H H3B 0.269(4) 0.9652(18) 0.7094(10) 0.026 Uiso d 1
C C4B 0.3886(3) 0.83923(16) 0.65271(8) 0.0204(4) Uani d 1
H H4B 0.264(4) 0.8230(17) 0.6288(10) 0.024 Uiso d 1
C C5B 0.5396(3) 0.97127(19) 0.80411(9) 0.0266(4) Uani d 1
H H51B 0.455(4) 1.043(2) 0.8066(11) 0.040 Uiso d 1
H H52B 0.672(4) 0.982(2) 0.8270(11) 0.040 Uiso d 1
H H53B 0.451(4) 0.914(2) 0.8248(11) 0.040 Uiso d 1
C C6B 0.7177(4) 1.03343(17) 0.70313(10) 0.0289(5) Uani d 1
H H61B 0.756(4) 1.010(2) 0.6609(12) 0.043 Uiso d 1
H H62B 0.849(4) 1.049(2) 0.7261(12) 0.043 Uiso d 1
H H63B 0.631(4) 1.107(2) 0.7017(11) 0.043 Uiso d 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C6A C1A C2A 116.68(16)
C6A C1A C3 123.98(16)
C2A C1A C3 119.33(16)
O2A C2A C3A 121.62(16)
O2A C2A C1A 116.49(15)
C3A C2A C1A 121.89(16)
C2A O2A H2A 109.7(16)
C2A C3A C4A 119.60(17)
C2A C3A H3A 120.3(12)
C4A C3A H3A 120.1(12)
O4A C4A C5A 122.99(16)
O4A C4A C3A 117.00(16)
C5A C4A C3A 120.01(16)
C4A O4A H4A 111.3(17)
C4A C5A C6A 119.34(17)
C4A C5A H5A 120.7(13)
C6A C5A H5A 119.9(13)
C5A C6A C1A 122.47(18)
C5A C6A H6A 118.6(13)
C1A C6A H6A 118.9(13)
C9 O1 C2 117.69(14)
O1 C2 C3 112.39(14)
O1 C2 H21 109.6(12)
C3 C2 H21 111.0(12)
O1 C2 H22 104.9(12)
C3 C2 H22 111.6(12)
H21 C2 H22 107.1(18)
C1A C3 C2 111.68(14)
C1A C3 C4 115.00(15)
C2 C3 C4 107.17(15)
C1A C3 H3 107.3(12)
C2 C3 H3 106.7(12)
C4 C3 H3 108.7(12)
C10 C4 C3 107.92(15)
C10 C4 H41 109.3(12)
C3 C4 H41 109.9(12)
C10 C4 H42 110.7(13)
C3 C4 H42 108.1(12)
H41 C4 H42 110.9(17)
C6 C5 C10 122.20(18)
C6 C5 H5 120.9(12)
C10 C5 H5 116.9(12)
C7 C6 C5 118.54(17)
C7 C6 H6 119.5(12)
C5 C6 H6 122.0(12)
C6 C7 O1B 117.95(15)
C6 C7 C8 121.89(16)
O1B C7 C8 119.96(16)
C7 C8 C9 117.87(17)
C7 C8 C4B 118.12(16)
C9 C8 C4B 123.89(16)
O1 C9 C10 123.05(16)
O1 C9 C8 115.22(16)
C10 C9 C8 121.69(16)
C5 C10 C9 117.82(16)
C5 C10 C4 121.88(16)
C9 C10 C4 120.12(16)
C7 O1B C2B 117.87(13)
O1B C2B C3B 109.77(14)
O1B C2B C5B 104.62(15)
C3B C2B C5B 111.45(16)
O1B C2B C6B 107.92(16)
C3B C2B C6B 111.20(16)
C5B C2B C6B 111.62(17)
C4B C3B C2B 121.07(17)
C4B C3B H3B 124.2(13)
C2B C3B H3B 114.7(12)
C3B C4B C8 120.24(17)
C3B C4B H4B 121.8(13)
C8 C4B H4B 117.9(13)
C2B C5B H51B 110.6(13)
C2B C5B H52B 108.8(14)
H51B C5B H52B 109(2)
C2B C5B H53B 112.0(14)
H51B C5B H53B 105.2(19)
H52B C5B H53B 111(2)
C2B C6B H61B 109.9(16)
C2B C6B H62B 112.3(15)
H61B C6B H62B 107(2)
C2B C6B H63B 109.4(14)
H61B C6B H63B 111(2)
H62B C6B H63B 107(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1A C6A 1.396(3)
C1A C2A 1.408(2)
C1A C3 1.516(2)
C2A O2A 1.376(2)
C2A C3A 1.393(3)
O2A H2A 0.84(3)
C3A C4A 1.396(3)
C3A H3A 0.94(2)
C4A O4A 1.369(2)
C4A C5A 1.389(3)
O4A H4A 0.86(3)
C5A C6A 1.396(3)
C5A H5A 0.97(2)
C6A H6A 0.96(2)
O1 C9 1.375(2)
O1 C2 1.455(2)
C2 C3 1.525(3)
C2 H21 0.99(2)
C2 H22 1.00(2)
C3 C4 1.536(3)
C3 H3 0.97(2)
C4 C10 1.508(2)
C4 H41 0.99(2)
C4 H42 0.98(2)
C5 C6 1.392(3)
C5 C10 1.394(3)
C5 H5 0.97(2)
C6 C7 1.384(3)
C6 H6 0.98(2)
C7 O1B 1.389(2)
C7 C8 1.401(3)
C8 C9 1.406(2)
C8 C4B 1.459(3)
C9 C10 1.400(3)
O1B C2B 1.471(2)
C2B C3B 1.512(3)
C2B C5B 1.521(3)
C2B C6B 1.526(3)
C3B C4B 1.337(3)
C3B H3B 1.00(2)
C4B H4B 0.96(2)
C5B H51B 1.01(3)
C5B H52B 0.98(3)
C5B H53B 0.99(3)
C6B H61B 0.96(3)
C6B H62B 0.99(3)
C6B H63B 1.04(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_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
O4A H4A O1B 1_555 1_555 4_664 0.86(3) 1.96(3) 2.8214(19) 178(2) y
O2A H2A CgA 1_555 1_555 2_565 0.84(3) 2.46(2) 3.1505(16) 139(2) y
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6A C1A C2A O2A -179.56(15)
C3 C1A C2A O2A 1.4(2)
C6A C1A C2A C3A 0.5(2)
C3 C1A C2A C3A -178.56(16)
O2A C2A C3A C4A 179.01(16)
C1A C2A C3A C4A -1.0(3)
C2A C3A C4A O4A -179.39(16)
C2A C3A C4A C5A 0.8(3)
O4A C4A C5A C6A -179.83(17)
C3A C4A C5A C6A 0.0(3)
C4A C5A C6A C1A -0.6(3)
C2A C1A C6A C5A 0.3(3)
C3 C1A C6A C5A 179.32(16)
C9 O1 C2 C3 31.4(2)
C6A C1A C3 C2 100.6(2)
C2A C1A C3 C2 -80.5(2)
C6A C1A C3 C4 -21.8(2)
C2A C1A C3 C4 157.13(16)
O1 C2 C3 C1A 172.12(15)
O1 C2 C3 C4 -61.09(19)
C1A C3 C4 C10 -177.75(14)
C2 C3 C4 C10 57.45(18)
C10 C5 C6 C7 -0.2(3)
C5 C6 C7 O1B 174.93(16)
C5 C6 C7 C8 0.1(3)
C6 C7 C8 C9 0.4(3)
O1B C7 C8 C9 -174.32(15)
C6 C7 C8 C4B 176.53(17)
O1B C7 C8 C4B 1.8(2)
C2 O1 C9 C10 0.9(2)
C2 O1 C9 C8 -176.83(15)
C7 C8 C9 O1 176.92(15)
C4B C8 C9 O1 1.0(2)
C7 C8 C9 C10 -0.9(2)
C4B C8 C9 C10 -176.78(17)
C6 C5 C10 C9 -0.3(3)
C6 C5 C10 C4 -175.28(17)
O1 C9 C10 C5 -176.79(16)
C8 C9 C10 C5 0.8(2)
O1 C9 C10 C4 -1.7(3)
C8 C9 C10 C4 175.90(16)
C3 C4 C10 C5 146.12(17)
C3 C4 C10 C9 -28.8(2)
C6 C7 O1B C2B 154.92(16)
C8 C7 O1B C2B -30.2(2)
C7 O1B C2B C3B 42.0(2)
C7 O1B C2B C5B 161.71(15)
C7 O1B C2B C6B -79.32(19)
O1B C2B C3B C4B -29.3(2)
C5B C2B C3B C4B -144.71(18)
C6B C2B C3B C4B 90.1(2)
C2B C3B C4B C8 3.9(3)
C7 C8 C4B C3B 11.4(3)
C9 C8 C4B C3B -172.65(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 124052
