Psiguadiols A–J, Rearranged Meroterpenoids as Potent PTP1B Inhibitors from Psidium guajava
Hou, Ji-Qin; Fan, Chun-Lin; Pei, Xin; Zhang, Pei-Lin; Deng, Fan; Jiang, Wan-Qiang; Wang, Guo-Cai; Zhang, Xiao-Qi; Ye, Wen-Cai; Wang, Hao; Journal of Natural Products  (2019) –; doi:10.1021/acs.jnatprod.9b00333

data_1552925
_publ_section_title
;
 Psiguadiols A--J, Rearranged Meroterpenoids as Potent PTP1B Inhibitors
 from Psidium guajava
;
_journal_name_full               'Journal of Natural Products'
_journal_paper_doi               10.1021/acs.jnatprod.9b00333
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C30 H34 O6'
_chemical_formula_sum            'C30 H34 O6'
_chemical_formula_weight         490.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.413(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.9365(7)
_cell_length_b                   8.3642(4)
_cell_length_c                   16.9500(5)
_cell_measurement_reflns_used    4431
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.60
_cell_measurement_theta_min      2.72
_cell_volume                     2711.28(19)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16778
_diffrn_reflns_point_group_measured_fraction_full 0.929
_diffrn_reflns_point_group_measured_fraction_max 0.929
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         2.718
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 1747 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.23(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4431
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0807P)^2^+7.3580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1620
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.854
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                4302
_reflns_number_total             4431
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00333_si_004.cif
_cod_data_source_block           ja
_cod_database_code               1552925
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H25), C11(H11), C9(H9), C6(H6), C5(H5A)
2.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C16(H16A,H16B), C8(H8A,H8B)
2.c Me refined with riding coordinates:
 C17(H17A,H17B,H17C), C10(H10A,H10B,H10C), C4(H4A,H4B,H4C), C2(H2A,H2B,H2C)
2.d Aromatic/amide H refined with riding coordinates:
 C23(H23), C21(H21), C20(H20), C18(H18), C14(H14), C13(H13), C12(H12), C3(H3)
2.e Tetrahedral OH refined with riding coordinates:
 O5(H5), O1(H1)
2.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              76522
_shelx_hkl_checksum              92113
_shelx_fab_checksum              42888
_olex2_submission_special_instructions 'No special instructions were received'