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_1560289
_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         'C18 H22 O6'
_chemical_formula_sum            'C18 H22 O6'
_chemical_formula_weight         334.35
_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             2020-11-12
_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                   5.41732(3)
_cell_length_b                   15.13174(9)
_cell_length_c                   20.13674(12)
_cell_measurement_reflns_used    13284
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      73.4490
_cell_measurement_theta_min      3.6330
_cell_volume                     1650.679(17)
_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      99.98(10)
_diffrn_measured_fraction_theta_full 1.000
_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    -16.00  28.00   0.50    0.50    --    0.00 -82.00   0.00   88
  2  \w    -33.00  31.00   0.50    0.50    --    0.00 -82.00-180.00  128
  3  \w    -10.00  26.00   0.50    0.50    --    0.00 -82.00 -60.00   72
  4  \w    -23.00   5.00   0.50    0.50    --    0.00 -82.00 120.00   56
  5  \w    -20.00  55.00   0.50    0.50    --    0.00  54.00 158.55  150
  6  \w      6.00  37.00   0.50    0.50    --   94.60 -61.00 150.00   62
  7  \w      5.00 101.00   0.50    0.50    --   94.60 -15.00  30.00  192
  8  \w     23.00 126.00   0.50    0.50    --   94.60 -82.00 -90.00  206
  9  \w     18.00 107.00   0.50    0.50    --   94.60 -61.00 -90.00  178
 10  \w     72.00 100.00   0.50    0.50    --   94.60 -82.00  60.00   56
 11  \w      7.00 101.00   0.50    0.50    --   94.60 -45.00 150.00  188
 12  \w     12.00 100.00   0.50    0.50    --   94.60 -30.00 -30.00  176
 13  \w     14.00  40.00   0.50    0.50    --   94.60 -82.00  30.00   52
 14  \w     52.00 125.00   0.50    0.50    --   94.60 -82.00  30.00  146
 15  \w     75.00 115.00   0.50    0.50    --   94.60 -82.00 150.00   80
 16  \w     49.00  99.00   0.50    0.50    --   94.60 -61.00 150.00  100
 17  \w     19.00  44.00   0.50    0.50    --   94.60 -82.00 -30.00   50
 18  \w     84.00 117.00   0.50    0.50    --   94.60 -82.00 -30.00   66
 19  \w      8.00  34.00   0.50    0.50    --   94.60 -77.00  60.00   52
 20  \w     46.00 104.00   0.50    0.50    --   94.60 -82.00  90.00  116
 21  \w     16.00 175.00   0.50    0.50    --   94.60   0.00-150.00  318
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            16345
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.904
_diffrn_reflns_theta_min         3.654
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74984
_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    1.345
_exptl_crystal_description       needle
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_extinction_coef       0.0016(4)
_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   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0373P)^2^+0.5135P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0763
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3251
_reflns_number_total             3303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01344_si_002.cif
_cod_data_source_block           20190702_tof-58
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_database_code               1560289
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.787
_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), C4'(H4')
2.b Secondary CH2 refined with riding coordinates:
 C3'(H3'A,H3'B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1'(H1'), C2'(H2'), C10(H10), C12(H12)
2.d Idealised Me refined as rotating group:
 C5'(H5'A,H5'B,H5'C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O5(H5), 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
;