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_1560284
_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         'C16 H22 O5, C H4 O'
_chemical_formula_sum            'C17 H26 O6'
_chemical_formula_weight         326.38
_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             2020-11-12
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6233(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.61617(17)
_cell_length_b                   16.0717(3)
_cell_length_c                   12.1358(3)
_cell_measurement_reflns_used    7269
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.7610
_cell_measurement_theta_min      3.6460
_cell_volume                     1680.42(6)
_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      100.00(10)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.977
_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    -30.00   7.00   0.50    2.00    --    0.00 -82.00   0.00   74
  2  \w    -15.00  46.00   0.50    2.00    --    0.00  38.00  60.00  122
  3  \w    -11.00  31.00   0.50    2.00    --    0.00 -82.00-120.00   84
  4  \w    -14.00  31.00   0.50    2.00    --    0.00 -82.00 -60.00   90
  5  \w    -33.00  28.00   0.50    2.00    --    0.00 -82.00  60.00  122
  6  \w      6.00  32.00   0.50    2.00    --    0.00  38.00-180.00   52
  7  \w     19.00 118.00   0.50    6.00    --   94.60 -61.00 150.00  198
  8  \w     77.00 179.00   0.50    6.00    --   94.60  45.00-120.00  204
  9  \w      8.00 112.00   0.50    6.00    --   94.60 -77.00 -60.00  208
 10  \w     77.00 162.00   0.50    6.00    --   94.60  45.00 -90.00  170
 11  \w      6.00 108.00   0.50    6.00    --   94.60 -61.00  30.00  204
 12  \w     71.00 119.00   0.50    6.00    --   94.60  61.00 150.00   96
 13  \w    127.00 167.00   0.50    6.00    --   94.60  61.00 150.00   80
 14  \w     91.00 145.00   0.50    6.00    --   94.60  82.00   0.00  108
 15  \w     11.00  36.00   0.50    6.00    --   94.60 -15.00-180.00   50
 16  \w     73.00 184.00   0.50    6.00    --   94.60  61.00 120.00  222
 17  \w     33.00 117.00   0.50    6.00    --   94.60 -82.00  30.00  168
 18  \w     53.00  78.00   0.50    6.00    --   94.60 -15.00-180.00   50
 19  \w    110.00 175.00   0.50    6.00    --   94.60  45.00 -60.00  130
 20  \w     77.00 102.00   0.50    6.00    --   94.60 -82.00  60.00   50
 21  \w      6.00 123.00   0.50    6.00    --   94.60 -82.00 150.00  234
;
_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  0.0503
_diffrn_reflns_av_unetI/netI     0.0565
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17322
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.917
_diffrn_reflns_theta_min         3.642
_exptl_absorpt_coefficient_mu    0.802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49960
_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    1.290
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2273 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.22(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6412
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0640P)^2^+0.5627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1336
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                5614
_reflns_number_total             6412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01344_si_004.cif
_cod_data_source_block           20200727_pss-111
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_database_code               1560284
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.976
_shelx_estimated_absorpt_t_min   0.795
_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:
 C2'(H2'), C3(H3), C2A'(H2A'), C3A(H3AA)
2.b Secondary CH2 refined with riding coordinates:
 C1'(H1'A,H1'B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,
 H8B), C1A'(H1AA,H1AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB),
 C7A(H7AA,H7AB), C8A(H8AA,H8AB)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C10A(H10A), C12A(H12A)
2.d Idealised Me refined as rotating group:
 C3'(H3'A,H3'B,H3'C), C3A'(H3AB,H3AC,H3AD), C1S(H1SA,H1SB,H1SC), C2S(H2SA,H2SB,
 H2SC)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O4(H4), O5(H5), O3A(H3AE), O4A(H4AC), O5A(H5AC), O1S(H1S), O2S(H2S)
;
_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
;