Bipolaquinones A-J, Immunosuppressive Meroterpenoids from a Soil-Derived <i>Bipolaris zeicola</i>.
Liu, Mengting; Gu, Lianghu; Shen, Ling; Zhang, Xueke; Lin, Shuang; Ye, Ying; Wang, Jianping; Hu, Zhengxi; Zhang, Yonghui; Journal of natural products 84 (2021) 2427–2436; doi:10.1021/acs.jnatprod.1c00327

data_1564804
_publ_section_title
;
 Bipolaquinones A-J, Immunosuppressive Meroterpenoids from a Soil-Derived
 <i>Bipolaris zeicola</i>.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2427
_journal_page_last               2436
_journal_paper_doi               10.1021/acs.jnatprod.1c00327
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H44 O6, C H4 O'
_chemical_formula_sum            'C31 H48 O7'
_chemical_formula_weight         532.69
_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             2018-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.4044(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.89568(5)
_cell_length_b                   7.73002(3)
_cell_length_c                   16.47814(8)
_cell_measurement_reflns_used    27868
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6000
_cell_measurement_theta_min      2.7320
_cell_volume                     1490.314(11)
_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    'XS (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 0.994
_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    -62.00 -31.00   0.50    0.50    --    0.00 -42.00 122.00   62
  2  \w    -26.00  18.00   0.50    0.50    --    0.00 -42.00 122.00   88
  3  \w     77.00 108.00   0.50    0.50    --   94.60 -42.00 122.00   62
  4  \w     78.00 178.00   0.50    0.50    --   94.60  42.00 -85.00  200
  5  \w     34.00  60.00   0.50    0.50    --    0.00  38.00-150.00   52
  6  \w    -17.00  23.00   0.50    0.50    --    0.00  38.00-150.00   80
  7  \w    -56.00  18.00   0.50    0.50    --    0.00 -19.00  30.00  148
  8  \w     -8.00  87.00   0.50    0.50    --    0.00  38.00   0.00  190
  9  \w    -18.00  32.00   0.50    0.50    --    0.00  42.00 -85.00  100
 10  \w     13.00  89.00   0.50    0.50    --    0.00  57.00-180.00  152
 11  \w    -46.00  10.00   0.50    0.50    --    0.00 -77.00  60.00  112
 12  \w      0.00  83.00   0.50    0.50    --    0.00  57.00  30.00  166
 13  \w     42.00  71.00   0.50    0.50    --    0.00  42.00 -85.00   58
 14  \w    -21.00   4.00   0.50    0.50    --    0.00  57.00-180.00   50
 15  \w    123.00 149.00   0.50    0.50    --   94.60  67.00 162.28   52
 16  \w     10.00  42.00   0.50    0.50    --   94.60 -82.00 -90.00   64
 17  \w     51.00 122.00   0.50    0.50    --   94.60 -82.00 -90.00  142
 18  \w     70.00  99.00   0.50    0.50    --   94.60  65.00  -0.43   58
 19  \w     71.00 157.00   0.50    0.50    --   94.60  61.00  88.19  172
 20  \w     71.00  99.00   0.50    0.50    --   94.60  67.00 162.28   56
 21  \w     66.00 184.00   0.50    0.50    --   94.60  74.00  51.43  236
 22  \w     35.00 125.00   0.50    0.50    --   94.60 -82.00 120.00  180
 23  \w     71.00 183.00   0.50    0.50    --   94.60  61.00 150.00  224
 24  \w     72.00 181.00   0.50    0.50    --   94.60  58.00 -43.87  218
 25  \w     67.00  93.00   0.50    0.50    --   94.60  74.00 114.49   52
 26  \w     69.00  95.00   0.50    0.50    --   94.60  67.00 -41.48   52
 27  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  30.00   52
 28  \w     71.00 107.00   0.50    0.50    --   94.60  61.00 -60.00   72
 29  \w    134.00 160.00   0.50    0.50    --   94.60  61.00 -60.00   52
 30  \w     52.00 123.00   0.50    0.50    --   94.60 -82.00  60.00  142
 31  \w     71.00 182.00   0.50    0.50    --   94.60  61.00-180.00  222
 32  \w     69.00 101.00   0.50    0.50    --   94.60  66.00-119.60   64
 33  \w     71.00 181.00   0.50    0.50    --   94.60  61.00 120.00  220
 34  \w     17.00 122.00   0.50    0.50    --   94.60 -77.00-180.00  210
 35  \w     74.00 138.00   0.50    0.50    --   94.60  50.00  30.72  128
 36  \w    147.00 172.00   0.50    0.50    --   94.60  73.00-112.86   50
 37  \w     71.00  96.00   0.50    0.50    --   94.60  61.00 -83.57   50
 38  \w    153.00 178.00   0.50    0.50    --   94.60  45.00  60.00   50
 39  \w     67.00  92.00   0.50    0.50    --   94.60  73.00-112.86   50
 40  \w    142.00 168.00   0.50    0.50    --   94.60  65.00 -82.34   52
 41  \w     68.00  94.00   0.50    0.50    --   94.60  69.00  99.44   52
 42  \w    130.00 166.00   0.50    0.50    --   94.60  69.00  99.44   72
 43  \w     68.00  93.00   0.50    0.50    --   94.60  73.00  78.22   50
 44  \w     50.00 109.00   0.50    0.50    --   94.60 -77.00   0.00  118
 45  \w     75.00 126.00   0.50    0.50    --   94.60  45.00  60.00  102
 46  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 148.21   50
 47  \w    140.00 168.00   0.50    0.50    --   94.60  65.00  -0.43   56
 48  \w     70.00 127.00   0.50    0.50    --   94.60  65.00 -82.34  114
 49  \w     71.00 101.00   0.50    0.50    --   94.60  61.00 -13.92   60
 50  \w     68.00  94.00   0.50    0.50    --   94.60  69.00-170.87   52
 51  \w     68.00  93.00   0.50    0.50    --   94.60  69.00  39.17   50
 52  \w     67.00 179.00   0.50    0.50    --   94.60  73.00-165.47  224
 53  \w     68.00  94.00   0.50    0.50    --   94.60  73.00 -40.55   52
 54  \w     69.00  94.00   0.50    0.50    --   94.60  67.00  49.77   50
 55  \w     67.00  93.00   0.50    0.50    --   94.60  72.00-142.94   52
 56  \w    130.00 168.00   0.50    0.50    --   94.60  72.00-142.94   76
 57  \w     38.00 122.00   0.50    0.50    --   94.60 -82.00 -30.00  168
;
_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      0.0206252000
_diffrn_orient_matrix_UB_12      -0.1724062000
_diffrn_orient_matrix_UB_13      0.0472134000
_diffrn_orient_matrix_UB_21      0.1296778000
_diffrn_orient_matrix_UB_22      0.0345859000
_diffrn_orient_matrix_UB_23      0.0160755000
_diffrn_orient_matrix_UB_31      -0.0098347000
_diffrn_orient_matrix_UB_32      0.0937950000
_diffrn_orient_matrix_UB_33      0.0809199000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            34185
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.967
_diffrn_reflns_theta_min         2.726
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78186
_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            colorless
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 2656 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         5957
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0436P)^2^+1.0674P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1025
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                5902
_reflns_number_total             5957
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00327_si_003.cif
_cod_data_source_block           20181127_lmt3-64-8
_cod_database_code               1564804
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.925
_shelx_estimated_absorpt_t_min   0.852
_reflns_odcompleteness_completeness 100.00
_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:
 C4(H4), C8(H8), C20(H20), C21(H21), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,H10B), C26(H26A,H26B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C18(H18)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A), O7(H7)
;
_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 1.216
_oxdiff_exptl_absorpt_empirical_full_min 0.740