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_1560288
_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 H24 O6'
_chemical_formula_sum            'C18 H24 O6'
_chemical_formula_weight         336.37
_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                   5.46419(2)
_cell_length_b                   15.26209(6)
_cell_length_c                   20.85735(10)
_cell_measurement_reflns_used    33274
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      73.7080
_cell_measurement_theta_min      5.1240
_cell_volume                     1739.398(13)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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    -45.00 -10.00   0.50    0.50    --    0.00  -8.00-166.00   70
  2  \w     59.00  85.00   0.50    0.50    --    0.00   8.00   7.00   52
  3  \w     66.00  95.00   0.50    0.50    --   94.60  -8.00-166.00   58
  4  \w    150.00 177.00   0.50    0.50    --   94.60   8.00   7.00   54
  5  \w    -22.00  89.00   0.50    0.50    --    0.00  57.00   0.00  222
  6  \w     17.00  55.00   0.50    0.50    --    0.00  57.00  60.00   76
  7  \w    -22.00   6.00   0.50    0.50    --    0.00  57.00  60.00   56
  8  \w    -17.00  24.00   0.50    0.50    --    0.00  38.00 -60.00   82
  9  \w    -32.00  31.00   0.50    0.50    --    0.00 -82.00 -30.00  126
 10  \w     34.00  71.00   0.50    0.50    --    0.00  38.00 -60.00   74
 11  \w    -18.00  83.00   0.50    0.50    --    0.00  19.00 120.00  202
 12  \w      4.00  89.00   0.50    0.50    --    0.00  57.00 120.00  170
 13  \w     68.00 104.00   0.50    0.50    --   94.60  69.00  -2.30   72
 14  \w     90.00 126.00   0.50    0.50    --   94.60 -82.00-150.00   72
 15  \w     75.00 100.00   0.50    0.50    --   94.60  61.00 150.00   50
 16  \w     71.00 184.00   0.50    0.50    --   94.60  61.00 -30.00  226
 17  \w     71.00 102.00   0.50    0.50    --   94.60  61.00  90.00   62
 18  \w     69.00  94.00   0.50    0.50    --   94.60  68.00-172.64   50
 19  \w     90.00 124.00   0.50    0.50    --   94.60 -77.00   0.00   68
 20  \w      5.00  76.00   0.50    0.50    --   94.60 -82.00-150.00  142
 21  \w     70.00 120.00   0.50    0.50    --   94.60  63.00-128.33  100
 22  \w    159.00 184.00   0.50    0.50    --   94.60  56.00 -73.76   50
 23  \w    156.00 182.00   0.50    0.50    --   94.60  59.00  80.23   52
 24  \w    146.00 174.00   0.50    0.50    --   94.60  63.00-128.33   56
 25  \w     70.00  96.00   0.50    0.50    --   94.60  66.00 -15.57   52
 26  \w    132.00 157.00   0.50    0.50    --   94.60  66.00 -15.57   50
 27  \w      8.00  38.00   0.50    0.50    --   94.60 -82.00  60.00   60
 28  \w     43.00 126.00   0.50    0.50    --   94.60 -82.00  60.00  166
 29  \w     68.00 183.00   0.50    0.50    --   94.60  69.00  50.20  230
 30  \w     72.00 159.00   0.50    0.50    --   94.60  55.00 174.45  174
 31  \w     69.00  95.00   0.50    0.50    --   94.60  70.00-121.06   52
 32  \w     69.00  94.00   0.50    0.50    --   94.60  67.00 127.52   50
 33  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 120.00   50
 34  \w     71.00 149.00   0.50    0.50    --   94.60  61.00 -45.60  156
 35  \w     67.00 102.00   0.50    0.50    --   94.60  73.00  16.08   70
 36  \w     72.00 124.00   0.50    0.50    --   94.60  56.00 -73.76  104
 37  \w     71.00  99.00   0.50    0.50    --   94.60  61.00 -90.00   56
 38  \w     69.00  94.00   0.50    0.50    --   94.60  67.00 -82.19   50
 39  \w     67.00  93.00   0.50    0.50    --   94.60  73.00 -35.63   52
 40  \w    159.00 184.00   0.50    0.50    --   94.60  61.00 -60.00   50
 41  \w     67.00  93.00   0.50    0.50    --   94.60  73.00  82.72   52
 42  \w     66.00 174.00   0.50    0.50    --   94.60  75.00  25.14  216
 43  \w     75.00 135.00   0.50    0.50    --   94.60  45.00 150.00  120
 44  \w     72.00 146.00   0.50    0.50    --   94.60  61.00   0.00  148
 45  \w     66.00  92.00   0.50    0.50    --   94.60  74.00 128.41   52
 46  \w     29.00  69.00   0.50    0.50    --   94.60 -82.00-120.00   80
 47  \w     80.00 126.00   0.50    0.50    --   94.60 -82.00-120.00   92
 48  \w     73.00 184.00   0.50    0.50    --   94.60  53.00-129.36  222
 49  \w     67.00  92.00   0.50    0.50    --   94.60  72.00 159.29   50
 50  \w     72.00 183.00   0.50    0.50    --   94.60  56.00-162.43  222
 51  \w     68.00  94.00   0.50    0.50    --   94.60  71.00-167.41   52
 52  \w     67.00  93.00   0.50    0.50    --   94.60  72.00-133.87   52
 53  \w     72.00  97.00   0.50    0.50    --   94.60  57.00  59.24   50
 54  \w    141.00 172.00   0.50    0.50    --   94.60  57.00  59.24   62
 55  \w     68.00  94.00   0.50    0.50    --   94.60  72.00  90.52   52
 56  \w      6.00 120.00   0.50    0.50    --   94.60 -82.00 -30.00  228
 57  \w     72.00 148.00   0.50    0.50    --   94.60  61.00 -60.00  152
 58  \w    159.00 184.00   0.50    0.50    --   94.60  69.00  -2.30   50
 59  \w     71.00  96.00   0.50    0.50    --   94.60  59.00  80.23   50
 60  \w      7.00  82.00   0.50    0.50    --   94.60 -77.00   0.00  150
 61  \w     68.00  94.00   0.50    0.50    --   94.60  69.00-112.15   52
 62  \w    126.00 179.00   0.50    0.50    --   94.60  69.00-112.15  106
 63  \w     21.00 122.00   0.50    0.50    --   94.60 -82.00 150.00  202
;
_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  0.0163
_diffrn_reflns_av_unetI/netI     0.0062
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            42620
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.929
_diffrn_reflns_theta_min         3.589
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81789
_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    1.284
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details
;
 Flack x determined using 1423 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.016(18)
_refine_ls_extinction_coef       0.0061(5)
_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   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0362P)^2^+0.1593P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0705
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3460
_reflns_number_total             3493
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01344_si_003.cif
_cod_data_source_block           20190930_tof-72
_cod_depositor_comments
'Adding full bibliography for 1560283--1560291.cif.'
_cod_database_code               1560288
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.870
_shelx_estimated_absorpt_t_min   0.826
_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:
 C4'(H4'), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C3'(H3'A,H3'B), C2'(H2'A,H2'B), C1'(H1'A,H1'B), C4(H4A,H4B), C5(H5A,H5B),
 C6(H6A,H6B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 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
;