Enantiomeric 3-arylcoumarins and 2-arylcoumarones from the roots of Glycyrrhiza uralensis as protein tyrosine phosphatase 1B (PTP1B) inhibitors
Ji, Shuai; Qiao, Xue; Li, Zi-wei; Wang, Yong-rui; Yu, Si-wang; Liang, Wen-fei; Lin, Xiong-hao; Ye, Min; RSC Adv. 5 (2015) 45258–; doi:10.1039/C5RA06452J

data_7220503
_publ_section_title
;
 Enantiomeric 3-arylcoumarins and 2-arylcoumarones from the roots of
 Glycyrrhiza uralensis as protein tyrosine phosphatase 1B (PTP1B)
 inhibitors
;
_journal_issue                   56
_journal_name_full               'RSC Adv.'
_journal_page_first              45258
_journal_paper_doi               10.1039/C5RA06452J
_journal_volume                  5
_journal_year                    2015
_chemical_compound_source        'Glycyrrhiza uralensis'
_chemical_formula_moiety         'C21 H20 O6'
_chemical_formula_sum            'C21 H20 O6'
_chemical_formula_weight         368.37
_chemical_name_systematic        'Glycyfuranocoumarin A'
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-01-30
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-04-09 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.33933(18)
_cell_length_b                   19.7504(4)
_cell_length_c                   9.61969(17)
_cell_measurement_reflns_used    13045
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      73.8230
_cell_measurement_theta_min      4.4440
_cell_volume                     1774.40(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -120.00  -37.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -19.0000 -150.0000 83

  2 omega  -34.00    5.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -19.0000 -150.0000 39

  3 omega    7.00   53.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056  -99.0000   90.0000 46

  4 omega   65.00   98.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -45.0000 -120.0000 33

  5 omega  117.00  172.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000   30.0000 55

  6 omega   33.00   84.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000  -60.0000 51

  7 omega   40.00  135.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -77.0000  120.0000 95

  8 omega   37.00   87.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -30.0000   30.0000 50

  9 omega -115.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -57.0000  120.0000 104

 10 omega -115.00  -11.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -57.0000    0.0000 104

 11 omega   80.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000  -30.0000 98

 12 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000 -150.0000 101

 13 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   30.0000  120.0000 101

 14 omega   23.00  109.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000  -60.0000 86

 15 omega   55.00  129.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056 -178.0000   30.0000 74

 16 omega   57.00  131.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6056  178.0000  -90.0000 74

 17 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  -90.0000 101

 18 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000   30.0000 101

 19 omega   80.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   45.0000  150.0000 98

 20 omega   23.00  109.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000   60.0000 86

 21 omega -119.00   -7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -77.0000 -120.0000 112

 22 omega -119.00   -7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -77.0000   60.0000 112

 23 omega   74.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000  -30.0000 104

 24 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000   60.0000 101

 25 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  -60.0000 101

 26 omega   74.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000 -150.0000 104

 27 omega  -50.00   35.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056   38.0000   30.0000 85

 28 omega -119.00   -7.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6056  -77.0000  -30.0000 112

 29 omega   23.00  109.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775  -94.0000 -120.0000 86

 30 omega   77.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   61.0000  150.0000 101

 31 omega   74.00  167.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000 -180.0000 93

 32 omega   74.00  178.00   1.0000    2.0900
omega____ theta____ kappa____ phi______ frames
    -      107.3775   77.0000   90.0000 104
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0503187000
_diffrn_orient_matrix_UB_12      0.0491283000
_diffrn_orient_matrix_UB_13      0.1145403000
_diffrn_orient_matrix_UB_21      -0.1072844000
_diffrn_orient_matrix_UB_22      -0.0534591000
_diffrn_orient_matrix_UB_23      0.0521085000
_diffrn_orient_matrix_UB_31      0.1148472000
_diffrn_orient_matrix_UB_32      -0.0284219000
_diffrn_orient_matrix_UB_33      0.0990588000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29236
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.758
_diffrn_reflns_theta_min         4.477
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.840
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       lamellar
_exptl_crystal_F_000             776
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/water'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(6)
_refine_ls_extinction_coef       0.0036(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0449P)^2^+0.2077P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0763
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                3367
_reflns_number_total             3570
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra06452j2.cif
_cod_data_source_block           exp_3566
_cod_database_code               7220503
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         C21H20O6
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.850
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Others
 Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C7A)=Sof(H7A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(C7)=Sof(H7)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=Sof(C20)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C7A(H7A)
3.b Me refined with riding coordinates:
 C21(H21A,H21B,H21C), C21(H21D,H21E,H21F)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C14(H14), C16(H16), C17(H17)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C19A(H19D,H19E,
 H19F), C20A(H20D,H20E,H20F)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'