Hypothemycin-Type Resorcylic Acid Lactones with Immunosuppressive Activities from a <i>Podospora</i> sp.
Gao, Ying; Duan, Fang-Fang; Liu, Lin; Peng, Xiao-Gang; Meng, Xiang-Gao; Ruan, Han-Li; Journal of natural products 84 (2021) 483–494; doi:10.1021/acs.jnatprod.0c01344

data_1560287
_publ_section_title
;
 Hypothemycin-Type Resorcylic Acid Lactones with Immunosuppressive
 Activities from a <i>Podospora</i> sp.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              483
_journal_page_last               494
_journal_paper_doi               10.1021/acs.jnatprod.0c01344
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H28 O7'
_chemical_formula_sum            'C22 H28 O7'
_chemical_formula_weight         404.44
_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             2020-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.6959(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.59493(8)
_cell_length_b                   16.1943(2)
_cell_length_c                   11.21004(14)
_cell_measurement_reflns_used    12565
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7890
_cell_measurement_theta_min      3.9830
_cell_volume                     1006.55(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_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     53.00  88.00   0.50    0.50    --    0.00  38.00 -90.00   70
  2  \w     51.00  80.00   0.50    0.50    --    0.00  38.00  30.00   58
  3  \w    -42.00  -2.00   0.50    0.50    --    0.00 -77.00 -60.00   80
  4  \w     56.00  82.00   0.50    0.50    --    0.00  19.00 -60.00   52
  5  \w     21.00  66.00   0.50    0.50    --    0.00  19.00-180.00   90
  6  \w    -18.00  30.00   0.50    0.50    --    0.00  19.00 -60.00   96
  7  \w    -13.00  36.00   0.50    0.50    --    0.00  38.00  30.00   98
  8  \w    -30.00  11.00   0.50    0.50    --    0.00 -82.00 -30.00   82
  9  \w    -11.00  18.00   0.50    0.50    --    0.00  38.00 -90.00   58
 10  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00-120.00  128
 11  \w      2.00  80.00   0.50    0.50    --    0.00  38.00  90.00  156
 12  \w    -18.00   8.00   0.50    0.50    --    0.00  19.00-180.00   52
 13  \w     70.00 179.00   0.50    2.00    --   94.60  65.00  78.44  218
 14  \w     70.00 177.00   0.50    2.00    --   94.60  65.00  60.13  214
 15  \w     68.00  94.00   0.50    2.00    --   94.60  70.00  86.71   52
 16  \w    106.00 184.00   0.50    2.00    --   94.60  67.00 133.52  156
 17  \w     69.00  99.00   0.50    2.00    --   94.60  67.00 133.52   60
 18  \w     67.00 138.00   0.50    2.00    --   94.60  71.00-139.18  142
 19  \w     70.00 107.00   0.50    2.00    --   94.60  63.00-137.25   74
 20  \w    137.00 179.00   0.50    2.00    --   94.60  54.00 -70.35   84
 21  \w     73.00 110.00   0.50    2.00    --   94.60  54.00 -70.35   74
 22  \w    155.00 184.00   0.50    2.00    --   94.60  69.00 -48.75   58
 23  \w     71.00 115.00   0.50    2.00    --   94.60  60.00 162.94   88
 24  \w    141.00 167.00   0.50    2.00    --   94.60  60.00 162.94   52
 25  \w     66.00  91.00   0.50    2.00    --   94.60  75.00 -31.66   50
 26  \w     13.00 117.00   0.50    2.00    --   94.60 -61.00 -30.00  208
 27  \w    133.00 158.00   0.50    2.00    --   94.60  74.00-166.79   50
 28  \w     38.00 122.00   0.50    2.00    --   94.60 -82.00  90.00  168
 29  \w     30.00  56.00   0.50    2.00    --   94.60 -82.00-150.00   52
 30  \w     76.00 122.00   0.50    2.00    --   94.60 -82.00-150.00   92
 31  \w     66.00  92.00   0.50    2.00    --   94.60  74.00-166.79   52
 32  \w     68.00  94.00   0.50    2.00    --   94.60  69.00 -48.75   52
 33  \w     67.00 182.00   0.50    2.00    --   94.60  73.00-125.00  230
 34  \w     72.00  98.00   0.50    2.00    --   94.60  61.00 -90.00   52
 35  \w     67.00 103.00   0.50    2.00    --   94.60  71.00 167.10   72
 36  \w     75.00 182.00   0.50    2.00    --   94.60  45.00-150.00  214
 37  \w      5.00 122.00   0.50    2.00    --   94.60 -82.00-180.00  234
 38  \w    134.00 181.00   0.50    2.00    --   94.60  61.00 -90.00   94
 39  \w     71.00 102.00   0.50    2.00    --   94.60  61.00 150.00   62
 40  \w     68.00  93.00   0.50    2.00    --   94.60  70.00 101.32   50
 41  \w    159.00 184.00   0.50    2.00    --   94.60  69.00   8.61   50
 42  \w     69.00  95.00   0.50    2.00    --   94.60  68.00 113.31   52
 43  \w     71.00 142.00   0.50    2.00    --   94.60  60.00  10.29  142
 44  \w    146.00 174.00   0.50    2.00    --   94.60  60.00  10.29   56
 45  \w     71.00 120.00   0.50    2.00    --   94.60  61.00 -30.00   98
 46  \w     72.00  98.00   0.50    2.00    --   94.60  61.00 -60.00   52
 47  \w     94.00 126.00   0.50    2.00    --   94.60 -82.00-120.00   64
 48  \w     70.00  96.00   0.50    2.00    --   94.60  69.00   8.61   52
 49  \w     67.00 109.00   0.50    2.00    --   94.60  71.00 -16.10   84
 50  \w     66.00 180.00   0.50    2.00    --   94.60  74.00  23.90  228
 51  \w    144.00 169.00   0.50    2.00    --   94.60  70.00  86.71   50
 52  \w    147.00 172.00   0.50    2.00    --   94.60  63.00-137.25   50
 53  \w     70.00  96.00   0.50    2.00    --   94.60  64.00  51.03   52
 54  \w     63.00 125.00   0.50    2.00    --   94.60 -82.00   0.00  124
 55  \w     72.00 119.00   0.50    2.00    --   94.60  56.00 -58.96   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0506037000
_diffrn_orient_matrix_UB_12      0.0716356000
_diffrn_orient_matrix_UB_13      0.0903213000
_diffrn_orient_matrix_UB_21      0.0820331000
_diffrn_orient_matrix_UB_22      -0.0623264000
_diffrn_orient_matrix_UB_23      0.1010331000
_diffrn_orient_matrix_UB_31      0.2605890000
_diffrn_orient_matrix_UB_32      0.0057087000
_diffrn_orient_matrix_UB_33      -0.0294977000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20220
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.917
_diffrn_reflns_theta_min         3.979
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (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    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 1740 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3983
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0723P)^2^+0.0897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1083
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                3815
_reflns_number_total             3983
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01344_si_010.cif
_cod_data_source_block           20200808_tof-9a_2
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_database_code               1560287
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.908
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C3(H3), C8(H8), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C16(H16)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_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 2.520
_oxdiff_exptl_absorpt_empirical_full_min 0.422