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_1560286
_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 H26 O6'
_chemical_formula_sum            'C19 H26 O6'
_chemical_formula_weight         350.40
_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             2019-05-07
_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            8
_cell_length_a                   5.51230(10)
_cell_length_b                   16.2923(2)
_cell_length_c                   39.6735(4)
_cell_measurement_reflns_used    19795
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.6140
_cell_measurement_theta_min      2.9270
_cell_volume                     3563.00(9)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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    -32.00  18.00   0.50    1.20    --    0.00 -82.00  90.00  100
  2  \w    -22.00  29.00   0.50    1.20    --    0.00  57.00  60.00  102
  3  \w    -25.00   1.00   0.50    1.20    --    0.00 -82.00  60.00   52
  4  \w    -39.00   5.00   0.50    1.20    --    0.00 -77.00-120.00   88
  5  \w    -25.00  28.00   0.50    1.20    --    0.00  67.00 -73.93  106
  6  \w    -33.00  10.00   0.50    1.20    --    0.00 -82.00 -60.00   86
  7  \w     73.00  99.00   0.50    5.00    --   94.60 -82.00-180.00   52
  8  \w     13.00  38.00   0.50    5.00    --   94.60 -82.00-180.00   50
  9  \w     71.00 184.00   0.50    5.00    --   94.60  15.00-120.00  226
 10  \w     27.00 118.00   0.50    5.00    --   94.60 -61.00-150.00  182
 11  \w      5.00 117.00   0.50    5.00    --   94.60 -61.00   0.00  224
 12  \w     94.00 125.00   0.50    5.00    --   94.60 -82.00   0.00   62
 13  \w     16.00 118.00   0.50    5.00    --   94.60 -61.00  90.00  204
 14  \w     23.00 110.00   0.50    5.00    --   94.60 -45.00-150.00  174
 15  \w    151.00 176.00   0.50    5.00    --   94.60  15.00  90.00   50
 16  \w     51.00  77.00   0.50    5.00    --   94.60 -82.00   0.00   52
 17  \w     71.00  99.00   0.50    5.00    --   94.60 -82.00-120.00   56
 18  \w     88.00 126.00   0.50    5.00    --   94.60  15.00  90.00   76
 19  \w     12.00  37.00   0.50    5.00    --   94.60 -82.00-120.00   50
 20  \w    131.00 182.00   0.50    5.00    --   94.60  30.00 -60.00  102
 21  \w     97.00 123.00   0.50    5.00    --   94.60 -82.00  60.00   52
 22  \w     83.00 109.00   0.50    5.00    --   94.60 -82.00 150.00   52
 23  \w     75.00 101.00   0.50    5.00    --   94.60 -82.00  30.00   52
 24  \w     97.00 179.00   0.50    5.00    --   94.60  77.00 120.00  164
 25  \w     30.00 120.00   0.50    5.00    --   94.60 -82.00  90.00  180
 26  \w     45.00 123.00   0.50    5.00    --   94.60 -82.00 -45.38  156
;
_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      0.0274394000
_diffrn_orient_matrix_UB_12      -0.0915375000
_diffrn_orient_matrix_UB_13      0.0089560000
_diffrn_orient_matrix_UB_21      -0.0452504000
_diffrn_orient_matrix_UB_22      -0.0230852000
_diffrn_orient_matrix_UB_23      -0.0371284000
_diffrn_orient_matrix_UB_31      0.2744241000
_diffrn_orient_matrix_UB_32      0.0053096000
_diffrn_orient_matrix_UB_33      -0.0070160000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0259
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            38601
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.943
_diffrn_reflns_theta_min         2.932
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86794
_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    1.306
_exptl_crystal_description       needle
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 2702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     461
_refine_ls_number_reflns         7111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0532P)^2^+1.4380P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                6779
_reflns_number_total             7111
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01344_si_007.cif
_cod_data_source_block           20190429_tof26
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_database_code               1560286
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.796
_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), C8(H8), C3A(H3AA), C7A(H7A), C8A(H8A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C4A(H4AA,
 H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C9A(H9AA,H9AB), C10A(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C16(H16), C11A(H11A), C12A(H12A), C14A(H14A),
 C16A(H16A)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C19A(H19D,H19E,H19F), C20A(H20D,
 H20E,H20F)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3A), O4(H4), O6(H6), O3A(H3AB), O4A(H4AC), O6A(H6AC)
;
_shelx_res_checksum              46336
_shelx_hkl_checksum              26653
_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 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.521