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_1552924
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.4127(4)
_cell_length_b                   17.8732(12)
_cell_length_c                   22.4543(14)
_cell_measurement_reflns_used    16427
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5210
_cell_measurement_theta_min      1.9340
_cell_volume                     2573.6(3)
_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, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -121.00   0.00   1.00    1.00    --  -40.73 -19.00-120.00  121
  2  \w   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00  30.00   99
  3  \w    -65.00  34.00   1.00    1.00    --  -40.73  38.00  60.00   99
  4  \w     27.00 100.00   1.00    1.00    --   40.73-132.00 -21.00   73
  5  \w    -31.00  69.00   1.00    1.00    --   40.73 -57.00-180.00  100
  6  \w     23.00  97.00   1.00    1.00    --   40.73-125.00 150.00   74
  7  \w     31.00 140.00   1.00    1.50    --  106.95 -77.00   0.00  109
  8  \w     81.00 178.00   1.00    1.50    --  106.95  45.00 -30.00   97
  9  \w     34.00 121.00   1.00    1.50    --  106.95-125.00 -90.00   87
 10  \w     25.00 109.00   1.00    1.50    --  106.95 -95.00  90.00   84
 11  \w     81.00 178.00   1.00    1.50    --  106.95  45.00 120.00   97
 12  \w     34.00 121.00   1.00    1.50    --  106.95-125.00  30.00   87
 13  \w     35.00 136.00   1.00    1.50    --  106.95 -61.00-180.00  101
 14  \w     31.00 140.00   1.00    1.50    --  106.95 -77.00 150.00  109
 15  \w     94.00 178.00   1.00    1.50    --  106.95 125.00  90.00   84
 16  \w     74.00 178.00   1.00    1.50    --  106.95  77.00 -90.00  104
 17  \w     78.00 178.00   1.00    1.50    --  106.95  61.00-180.00  100
 18  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00  30.00  109
 19  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 120.00  109
 20  \w   -113.00 -13.00   1.00    1.00    --  -40.73 -57.00 150.00  100
 21  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00-120.00  109
 22  \w   -117.00  -8.00   1.00    1.00    --  -40.73 -77.00 -30.00  109
 23  \w     81.00 178.00   1.00    1.50    --  106.95  45.00-120.00   97
 24  \w     74.00 178.00   1.00    1.50    --  106.95  77.00-180.00  104
 25  \w     79.00 178.00   1.00    1.50    --  106.95  30.00  60.00   99
 26  \w     74.00 178.00   1.00    1.50    --  106.95  77.00-120.00  104
 27  \w     78.00 178.00   1.00    1.50    --  106.95  61.00 150.00  100
 28  \w     74.00 178.00   1.00    1.50    --  106.95  77.00  60.00  104
 29  \w     74.00 141.00   1.00    1.50    --  106.95  77.00  30.00   67
 30  \w     78.00 178.00   1.00    1.50    --  106.95  61.00   0.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_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     1.54184
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            37802
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        61.165
_diffrn_reflns_theta_max         61.165
_diffrn_reflns_theta_min         1.968
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57821
_exptl_absorpt_correction_type   empirical
_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    1.266
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
;
 Flack x determined using 3146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(10)
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     535
_refine_ls_number_reflns         7904
_refine_ls_number_restraints     166
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0794
_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^)+(0.0508P)^2^+8.6340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.1959
_reflns_Friedel_coverage         0.928
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7454
_reflns_number_total             7904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00333_si_002.cif
_cod_data_source_block           pg-11-2
_cod_database_code               1552924
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.559(4)
 0.441(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C52-H52A = C52-H52B = C18-H18A = C18-H18B
 0.96 with sigma of 0.02
4. Rigid bond restraints
 C42, C47, C31, C34, C35, C38, C52, C7, C5, C8, C56, C44, C48, C50, C28, C9,
 C3, C19, C11, C33, C24, C37, C32, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
Uanis(C42) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C52) \\sim Ueq,
Uanis(C7) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C56) \\sim
Ueq, Uanis(C44) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C50) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C37) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C4) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(C42) = Uanis(C47) = Uanis(C31) = Uanis(C34) = Uanis(C35) = Uanis(C38) =
Uanis(C52) = Uanis(C7) = Uanis(C5) = Uanis(C8) = Uanis(C56) = Uanis(C44) =
Uanis(C48) = Uanis(C50) = Uanis(C28) = Uanis(C9) = Uanis(C3) = Uanis(C19) =
Uanis(C11) = Uanis(C33) = Uanis(C24) = Uanis(C37) = Uanis(C32) = Uanis(C4)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C41(H41), C50(H50), C10(H10), C55(H55), C20(H20), C24(H24), C56(H56)
6.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C22(H22A,H22B), C16(H16A,H16B), C23(H23A,H23B), C53(H53A,
 H53B), C49(H49A,H49B), C11(H11A,H11B), C48(H48A,H48B), C40(H40A,H40B),
 C57(H57A,H57B), C21(H21A,H21B), C54(H54A,H54B)
6.c Aromatic/amide H refined with riding coordinates:
 C38(H38), C30(H30), C5(H5), C46(H46), C29(H29), C26(H26), C27(H27), C1(H1),
 C42(H42), C44(H44), C31(H31), C43(H43), C28(H28), C45(H45)
6.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C60(H60A,H60B,H60C), C59(H59A,H59B,
 H59C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O9(H9), O8(H8), O2(H2), O12(H12), O6(H6)
;
_shelx_res_checksum              74451
_shelx_hkl_checksum              32840
_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
;