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_1552923
_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 ad
_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           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-07-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.9870(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.0507(2)
_cell_length_b                   9.4788(2)
_cell_length_c                   12.5781(2)
_cell_measurement_reflns_used    12237
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3790
_cell_measurement_theta_min      3.6060
_cell_volume                     1278.46(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -69.00  32.00   1.00    1.00    --  -40.73  57.00 -90.00  101
  2  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 -60.00  100
  3  \w    -82.00  39.00   1.00    1.00    --  -40.73  19.00-150.00  121
  4  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00-120.00  109
  5  \w     13.00 114.00   1.00    1.00    --   40.73  57.00 -90.00  101
  6  \w     23.00  97.00   1.00    1.00    --   40.73-125.00-180.00   74
  7  \w     13.00 114.00   1.00    1.00    --   40.73  57.00  30.00  101
  8  \w     16.00 115.00   1.00    1.00    --   40.73  38.00 -30.00   99
  9  \w     16.00 115.00   1.00    1.00    --   40.73  38.00 -90.00   99
 10  \w     81.00 178.00   1.00    1.00    --  106.95  45.00   0.00   97
 11  \w     74.00 101.00   1.00    1.00    --  106.95  77.00 -90.00   27
 12  \w     74.00 177.00   1.00    1.00    --  106.95  77.00-150.00  103
 13  \w    112.00 138.00   1.00    1.00    --  106.95  77.00 -90.00   26
 14  \w     78.00 105.00   1.00    1.00    --  106.95  61.00   0.00   27
 15  \w     74.00 100.00   1.00    1.00    --  106.95  77.00 -60.00   26
 16  \w     75.00 100.00   1.00    1.00    --  106.95  77.00   0.00   25
 17  \w     75.00 100.00   1.00    1.00    --  106.95  77.00 -30.00   25
 18  \w     79.00 104.00   1.00    1.00    --  106.95  61.00-120.00   25
 19  \w     29.00 114.00   1.00    1.00    --  106.95-107.00-115.00   85
 20  \w     26.00  98.00   1.00    1.00    --  106.95 -95.00 150.00   72
 21  \w     78.00 177.00   1.00    1.00    --  106.95  61.00 -60.00   99
 22  \w    125.00 155.00   1.00    1.00    --  106.95 125.00 -60.00   30
 23  \w     82.00 107.00   1.00    1.00    --  106.95  45.00 -90.00   25
 24  \w     82.00 109.00   1.00    1.00    --  106.95  45.00 -60.00   27
 25  \w     82.00 147.00   1.00    1.00    --  106.95  45.00  30.00   65
 26  \w     79.00 106.00   1.00    1.00    --  106.95  61.00 -90.00   27
 27  \w    116.00 178.00   1.00    1.00    --  106.95  77.00-120.00   62
 28  \w     78.00 107.00   1.00    1.00    --  106.95  61.00 -30.00   29
 29  \w     74.00 100.00   1.00    1.00    --  106.95  77.00-120.00   26
 30  \w     32.00 108.00   1.00    1.00    --  106.95 -95.00  60.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1405069000
_diffrn_orient_matrix_UB_12      0.0219092000
_diffrn_orient_matrix_UB_13      -0.0494496000
_diffrn_orient_matrix_UB_21      -0.0266680000
_diffrn_orient_matrix_UB_22      -0.0334452000
_diffrn_orient_matrix_UB_23      0.1120693000
_diffrn_orient_matrix_UB_31      0.0138295000
_diffrn_orient_matrix_UB_32      0.1574697000
_diffrn_orient_matrix_UB_33      0.0305811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13214
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.491
_diffrn_reflns_theta_min         3.621
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.103
_refine_ls_abs_structure_details
;
 Flack x determined using 1967 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0637P)^2^+0.1206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0935
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                4677
_reflns_number_total             4734
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00333_si_003.cif
_cod_data_source_block           pg-12
_cod_database_code               1552923
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H002(0.036) H003(0.04) H004(0.047) H00B(0.027) H00D(0.021)
 H00F(0.023) H00G(0.022) H00I(0.024) H00J(0.027) H00K(0.026) H00A(0.023)
 H00C(0.023) H00E(0.037) H00H(0.037) H00L(0.037) H00N(0.033) H00M(0.047)
 H00O(0.047) H00P(0.047) H00Q(0.033) H00R(0.031) H00T(0.029) H00S(0.031)
 H00U(0.031) H00V(0.031) H00W(0.031) H00X(0.032) H00Y(0.052) H(0.052) HA(0.052)
 H00Z(0.056) HB(0.056) HC(0.056) H010(0.037)
 Fixed X: H002(0.3211) H003(0.124) H004(0.1152) H00B(0.3927) H00D(0.2122)
 H00F(0.1323) H00G(0.1293) H00I(0.3139) H00J(0.2599) H00K(0.5251) H00A(0.3917)
 H00C(0.4239) H00E(-0.033) H00H(-0.005) H00L(-0.0082) H00N(0.5537) H00M(0.6199)
 H00O(0.7061) H00P(0.6211) H00Q(0.5702) H00R(0.422) H00T(0.1261) H00S(0.4432)
 H00U(0.4557) H00V(0.5439) H00W(0.6228) H00X(0.162) H00Y(0.2772) H(0.1315)
 HA(0.2147) H00Z(0.1988) HB(0.1384) HC(0.2839) H010(0.091)
 Fixed Y: H002(0.9661) H003(0.4441) H004(0.0349) H00B(0.5069) H00D(0.8147)
 H00F(0.6637) H00G(0.7043) H00I(0.9255) H00J(0.9023) H00K(0.6478) H00A(0.6053)
 H00C(0.7408) H00E(0.612) H00H(0.7647) H00L(0.6378) H00N(0.5812) H00M(0.8858)
 H00O(0.7727) H00P(0.7305) H00Q(0.8157) H00R(0.9765) H00T(0.8095) H00S(0.6831)
 H00U(0.8329) H00V(0.9231) H00W(0.7932) H00X(0.2545) H00Y(0.6488) H(0.6407)
 HA(0.5843) H00Z(1.0068) HB(0.9017) HC(0.9116) H010(0.1068)
 Fixed Z: H002(0.6561) H003(1.0772) H004(0.7788) H00B(0.9984) H00D(0.7527)
 H00F(0.4874) H00G(0.8734) H00I(0.4574) H00J(0.9615) H00K(0.6227) H00A(0.7444)
 H00C(0.8174) H00E(0.5848) H00H(0.6322) H00L(0.7114) H00N(1.1417) H00M(0.751)
 H00O(0.7158) H00P(0.794) H00Q(1.1938) H00R(1.1033) H00T(0.3626) H00S(0.4151)
 H00U(0.3657) H00V(0.5402) H00W(0.5189) H00X(0.5929) H00Y(0.2571) H(0.2345)
 HA(0.3454) H00Z(0.2873) HB(0.1931) HC(0.2337) H010(1.0283)
;
_shelx_res_checksum              66218
_shelx_hkl_checksum              64226
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.964
_oxdiff_exptl_absorpt_empirical_full_min 0.660