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_1560290
_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         'C19 H24 O6'
_chemical_formula_sum            'C19 H24 O6'
_chemical_formula_weight         348.38
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2020-11-09
_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                   6.92375(4)
_cell_length_b                   15.28917(6)
_cell_length_c                   17.20264(7)
_cell_measurement_reflns_used    33207
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.5050
_cell_measurement_theta_min      3.8530
_cell_volume                     1821.044(15)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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    -19.00   7.00   0.50    0.50    --    0.00  57.00  30.00   52
  2  \w     42.00  87.00   0.50    0.50    --    0.00  38.00-120.00   90
  3  \w     32.00  66.00   0.50    0.50    --    0.00  57.00  30.00   68
  4  \w    -23.00  24.00   0.50    0.50    --    0.00 -82.00 -90.00   94
  5  \w    -16.00  48.00   0.50    0.50    --    0.00  38.00 -90.00  128
  6  \w     52.00  79.00   0.50    0.50    --    0.00  38.00 -90.00   54
  7  \w    -17.00  85.00   0.50    0.50    --    0.00  38.00  30.00  204
  8  \w    -20.00  61.00   0.50    0.50    --    0.00  57.00 120.00  162
  9  \w    -18.00  31.00   0.50    0.50    --    0.00  19.00-180.00   98
 10  \w     46.00  84.00   0.50    0.50    --    0.00  19.00-180.00   76
 11  \w    -16.00  24.00   0.50    0.50    --    0.00  38.00-120.00   80
 12  \w     69.00 184.00   0.50    0.50    --   94.60  67.00 -54.07  230
 13  \w    154.00 181.00   0.50    0.50    --   94.60  66.00-140.50   54
 14  \w     70.00 182.00   0.50    0.50    --   94.60  63.00  20.76  224
 15  \w    131.00 177.00   0.50    0.50    --   94.60  65.00-101.94   92
 16  \w     70.00 106.00   0.50    0.50    --   94.60  65.00-101.94   72
 17  \w     69.00 104.00   0.50    0.50    --   94.60  66.00-140.50   70
 18  \w     73.00  99.00   0.50    0.50    --   94.60  53.00-176.37   52
 19  \w     69.00  95.00   0.50    0.50    --   94.60  67.00-166.11   52
 20  \w     68.00  94.00   0.50    0.50    --   94.60  70.00 143.97   52
 21  \w    150.00 175.00   0.50    0.50    --   94.60  75.00  40.13   50
 22  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 121.27   52
 23  \w     68.00  93.00   0.50    0.50    --   94.60  70.00 -19.09   50
 24  \w    137.00 163.00   0.50    0.50    --   94.60  70.00 -19.09   52
 25  \w     71.00  97.00   0.50    0.50    --   94.60  64.00-149.47   52
 26  \w     67.00 116.00   0.50    0.50    --   94.60  75.00  23.63   98
 27  \w     67.00  93.00   0.50    0.50    --   94.60  72.00 116.04   52
 28  \w     66.00  91.00   0.50    0.50    --   94.60  74.00  -7.60   50
 29  \w     67.00  93.00   0.50    0.50    --   94.60  72.00 -84.75   52
 30  \w     69.00  95.00   0.50    0.50    --   94.60  70.00-118.64   52
 31  \w     66.00 124.00   0.50    0.50    --   94.60  75.00  40.13  116
 32  \w     73.00 177.00   0.50    0.50    --   94.60  59.00-170.08  208
 33  \w     71.00 182.00   0.50    0.50    --   94.60  60.00  73.55  222
 34  \w     67.00  92.00   0.50    0.50    --   94.60  72.00  64.51   50
 35  \w     68.00  94.00   0.50    0.50    --   94.60  72.00 -52.02   52
 36  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  242
 37  \w     67.00  93.00   0.50    0.50    --   94.60  72.00  85.56   52
 38  \w    115.00 141.00   0.50    0.50    --   94.60  71.00 126.01   52
 39  \w    159.00 184.00   0.50    0.50    --   94.60  71.00  17.75   50
 40  \w     37.00 122.00   0.50    0.50    --   94.60 -82.00 -30.00  170
 41  \w     40.00 125.00   0.50    0.50    --   94.60 -82.00 -60.00  170
 42  \w     75.00 101.00   0.50    0.50    --   94.60  45.00   0.00   52
 43  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -30.00   52
 44  \w    111.00 184.00   0.50    0.50    --   94.60  61.00 -30.00  146
 45  \w     69.00 106.00   0.50    0.50    --   94.60  67.00 -85.79   74
 46  \w     71.00  97.00   0.50    0.50    --   94.60  61.00-180.00   52
 47  \w     71.00 112.00   0.50    0.50    --   94.60  61.00 -60.00   82
 48  \w    141.00 174.00   0.50    0.50    --   94.60  61.00 -60.00   66
 49  \w     71.00 178.00   0.50    0.50    --   94.60  61.00  90.00  214
 50  \w     71.00 113.00   0.50    0.50    --   94.60  61.00-150.00   84
 51  \w     71.00 182.00   0.50    0.50    --   94.60  61.00-120.00  222
 52  \w      6.00 124.00   0.50    0.50    --   94.60 -82.00-120.00  236
 53  \w     53.00 126.00   0.50    0.50    --   94.60 -82.00 150.00  146
 54  \w     67.00  93.00   0.50    0.50    --   94.60  71.00  17.75   52
 55  \w     67.00  94.00   0.50    0.50    --   94.60  71.00 126.01   54
 56  \w     75.00 159.00   0.50    0.50    --   94.60  46.00 129.15  168
 57  \w    119.00 182.00   0.50    0.50    --   94.60  54.00 171.41  126
 58  \w     71.00 104.00   0.50    0.50    --   94.60  61.00 -90.00   66
 59  \w     71.00 100.00   0.50    0.50    --   94.60  61.00 150.00   58
 60  \w    104.00 177.00   0.50    0.50    --   94.60  61.00 150.00  146
 61  \w     48.00 102.00   0.50    0.50    --   94.60 -82.00 120.00  108
 62  \w     74.00 100.00   0.50    0.50    --   94.60  54.00 171.41   52
;
_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      0.0077329000
_diffrn_orient_matrix_UB_12      -0.0031461000
_diffrn_orient_matrix_UB_13      -0.0894475000
_diffrn_orient_matrix_UB_21      0.0092245000
_diffrn_orient_matrix_UB_22      -0.1006119000
_diffrn_orient_matrix_UB_23      0.0029182000
_diffrn_orient_matrix_UB_31      -0.2222216000
_diffrn_orient_matrix_UB_32      -0.0042834000
_diffrn_orient_matrix_UB_33      -0.0029835000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0069
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44858
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.799
_diffrn_reflns_theta_min         3.868
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73544
_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    1.271
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 1504 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3661
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0573
_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^)+(0.1058P)^2^+0.3546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1597
_refine_ls_wR_factor_ref         0.1603
_reflns_Friedel_coverage         0.733
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                3597
_reflns_number_total             3661
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01344_si_006.cif
_cod_data_source_block           20190919_tof-101
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_original_cell_volume        1821.044(14)
_cod_database_code               1560290
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.926
_shelx_estimated_absorpt_t_min   0.885
_reflns_odcompleteness_completeness 99.53
_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)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), 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)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O6(H6)
;
_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 1.539
_oxdiff_exptl_absorpt_empirical_full_min 0.734