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_1560283
_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     dual
_audit_creation_date             2019-07-23
_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                   5.20899(3)
_cell_length_b                   13.13790(8)
_cell_length_c                   24.88894(15)
_cell_measurement_reflns_used    14110
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5210
_cell_measurement_theta_min      3.7850
_cell_volume                     1703.279(18)
_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    'XM (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     -9.00  25.00   0.50    0.50    --    0.00 -82.00 150.00   68
  2  \w    -11.00  22.00   0.50    0.50    --    0.00 -57.00-150.00   66
  3  \w    -11.00  29.00   0.50    0.50    --    0.00 -82.00  90.00   80
  4  \w    -46.00  10.00   0.50    0.50    --    0.00 -77.00  30.00  112
  5  \w     53.00  89.00   0.50    0.50    --    0.00  38.00 -90.00   72
  6  \w    -89.00 -54.00   0.50    0.50    --    0.00 -57.00-150.00   70
  7  \w      7.00  37.00   0.50    0.50    --   94.60 -82.00  90.00   60
  8  \w     94.00 180.00   0.50    0.50    --   94.60  45.00-120.00  172
  9  \w     49.00 126.00   0.50    0.50    --   94.60 -82.00 -90.00  154
 10  \w     62.00 126.00   0.50    0.50    --   94.60 -82.00-180.00  128
 11  \w     80.00 140.00   0.50    0.50    --   94.60  45.00 -90.00  120
 12  \w     14.00 105.00   0.50    0.50    --   94.60 -45.00 -60.00  182
 13  \w      6.00  32.00   0.50    0.50    --   94.60 -82.00   0.00   52
 14  \w     72.00 125.00   0.50    0.50    --   94.60 -82.00   0.00  106
 15  \w     36.00  73.00   0.50    0.50    --   94.60 -45.00 -90.00   74
 16  \w    122.00 181.00   0.50    0.50    --   94.60  30.00-180.00  118
 17  \w     46.00 117.00   0.50    0.50    --   94.60 -61.00 120.00  142
 18  \w      7.00  34.00   0.50    0.50    --   94.60 -61.00 120.00   54
 19  \w     45.00  87.00   0.50    0.50    --   94.60 -30.00-150.00   84
 20  \w     58.00 122.00   0.50    0.50    --   94.60 -82.00  90.00  128
 21  \w     10.00  99.00   0.50    0.50    --   94.60 -61.00  60.00  178
 22  \w     76.00 101.00   0.50    0.50    --   94.60 -82.00 -30.00   50
 23  \w      9.00 118.00   0.50    0.50    --   94.60 -15.00  90.00  218
;
_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      0.0858269000
_diffrn_orient_matrix_UB_12      0.0262820000
_diffrn_orient_matrix_UB_13      0.0575982000
_diffrn_orient_matrix_UB_21      0.0086962000
_diffrn_orient_matrix_UB_22      -0.1142037000
_diffrn_orient_matrix_UB_23      0.0139546000
_diffrn_orient_matrix_UB_31      0.2827892000
_diffrn_orient_matrix_UB_32      -0.0044840000
_diffrn_orient_matrix_UB_33      -0.0179061000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16711
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.828
_diffrn_reflns_theta_min         3.552
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54440
_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    1.359
_exptl_crystal_description       needle
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1371 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_extinction_coef       0.0030(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   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         3423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0256
_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^)+(0.0340P)^2^+0.4064P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0667
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3391
_reflns_number_total             3423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01344_si_005.cif
_cod_data_source_block           20190702_tof-93
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_original_cell_volume        1703.279(17)
_cod_database_code               1560283
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.960
_shelx_estimated_absorpt_t_min   0.788
_reflns_odcompleteness_completeness 99.95
_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), C7(H7)
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:
 O3(H3A), 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 1.657
_oxdiff_exptl_absorpt_empirical_full_min 0.498