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_1564805
_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'
_chemical_formula_sum            'C30 H44 O6'
_chemical_formula_weight         500.65
_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     dual
_audit_creation_date             2018-11-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 111.947(1)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.2607(1)
_cell_length_b                   10.2470(1)
_cell_length_c                   13.0776(2)
_cell_measurement_reflns_used    29128
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.6320
_cell_measurement_theta_min      4.2310
_cell_volume                     1399.65(3)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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    -35.00  -9.00   0.50    0.50    --    0.00 -78.00 -49.00   52
  2  \w     19.00  80.00   0.50    0.50    --   94.60 -78.00 -49.00  122
  3  \w    133.00 158.00   0.50    0.50    --   94.60  78.00  75.00   50
  4  \w    -21.00  13.00   0.50    0.50    --    0.00  57.00-120.00   68
  5  \w     58.00  89.00   0.50    0.50    --    0.00  57.00-120.00   62
  6  \w     -7.00  21.00   0.50    0.50    --    0.00 -57.00-180.00   56
  7  \w    -16.00  86.00   0.50    0.50    --    0.00  38.00  60.00  204
  8  \w      0.00  31.00   0.50    0.50    --    0.00 -82.00-150.00   62
  9  \w    -14.00  66.00   0.50    0.50    --    0.00  38.00 -60.00  160
 10  \w    -11.00  15.00   0.50    0.50    --    0.00 -38.00 120.00   52
 11  \w    -86.00 -41.00   0.50    0.50    --    0.00 -57.00-180.00   90
 12  \w    -85.00  19.00   0.50    0.50    --    0.00 -57.00  60.00  208
 13  \w    -88.00 -29.00   0.50    0.50    --    0.00 -38.00 120.00  118
 14  \w    134.00 165.00   0.50    0.50    --   94.60  61.00  60.00   62
 15  \w     72.00 157.00   0.50    0.50    --   94.60  61.00  90.00  170
 16  \w     24.00  51.00   0.50    0.50    --   94.60 -82.00  30.00   54
 17  \w     58.00 126.00   0.50    0.50    --   94.60 -82.00  30.00  136
 18  \w     66.00  91.00   0.50    0.50    --   94.60  74.00  35.73   50
 19  \w     73.00 105.00   0.50    0.50    --   94.60  61.00  60.00   64
 20  \w     70.00 182.00   0.50    0.50    --   94.60  63.00-159.76  224
 21  \w    136.00 162.00   0.50    0.50    --   94.60  74.00 144.95   52
 22  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 -25.23   50
 23  \w     71.00 132.00   0.50    0.50    --   94.60  61.00 150.00  122
 24  \w    133.00 159.00   0.50    0.50    --   94.60  73.00 -25.23   52
 25  \w     71.00  97.00   0.50    0.50    --   94.60  64.00  75.21   52
 26  \w     77.00 178.00   0.50    0.50    --   94.60  45.00  30.00  202
 27  \w     74.00 116.00   0.50    0.50    --   94.60  50.00 -87.61   84
 28  \w     71.00 182.00   0.50    0.50    --   94.60  60.00 108.33  222
 29  \w     68.00 125.00   0.50    0.50    --   94.60 -82.00-180.00  114
 30  \w     71.00  96.00   0.50    0.50    --   94.60  62.00 140.37   50
 31  \w     71.00 158.00   0.50    0.50    --   94.60  62.00-147.84  174
 32  \w     72.00 103.00   0.50    0.50    --   94.60  58.00 176.85   62
 33  \w      7.00 116.00   0.50    0.50    --   94.60 -82.00 -90.00  218
 34  \w     67.00  93.00   0.50    0.50    --   94.60  74.00 144.95   52
 35  \w    147.00 183.00   0.50    0.50    --   94.60  60.00 -63.41   72
 36  \w     71.00  96.00   0.50    0.50    --   94.60  60.00 -63.41   50
 37  \w    129.00 182.00   0.50    0.50    --   94.60  69.00-127.78  106
 38  \w     77.00 180.00   0.50    0.50    --   94.60  45.00 -60.00  206
 39  \w     66.00  94.00   0.50    0.50    --   94.60  75.00-109.86   56
 40  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  30.00   52
 41  \w     72.00  98.00   0.50    0.50    --   94.60  61.00 -60.00   52
 42  \w    107.00 183.00   0.50    0.50    --   94.60  74.00 167.95  152
 43  \w     67.00 184.00   0.50    0.50    --   94.60  71.00 -50.43  234
 44  \w     75.00 181.00   0.50    0.50    --   94.60  45.00   0.00  212
 45  \w     72.00 112.00   0.50    0.50    --   94.60  55.00  80.47   80
 46  \w     66.00  92.00   0.50    0.50    --   94.60  74.00 167.95   52
 47  \w     71.00  97.00   0.50    0.50    --   94.60  61.00   0.00   52
 48  \w    159.00 184.00   0.50    0.50    --   94.60  61.00   0.00   50
 49  \w     70.00  95.00   0.50    0.50    --   94.60  65.00  34.34   50
 50  \w     68.00  94.00   0.50    0.50    --   94.60  69.00-127.78   52
 51  \w     49.00  75.00   0.50    0.50    --   94.60 -82.00 -60.00   52
 52  \w     81.00 126.00   0.50    0.50    --   94.60 -82.00 -60.00   90
 53  \w     30.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  192
 54  \w     71.00 184.00   0.50    0.50    --   94.60  61.00 120.00  226
 55  \w     72.00 117.00   0.50    0.50    --   94.60  55.00-120.78   90
 56  \w     20.00 120.00   0.50    0.50    --   94.60 -82.00 120.00  200
;
_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      0.0738970000
_diffrn_orient_matrix_UB_12      0.0790533000
_diffrn_orient_matrix_UB_13      0.1047950000
_diffrn_orient_matrix_UB_21      0.1168511000
_diffrn_orient_matrix_UB_22      -0.0900266000
_diffrn_orient_matrix_UB_23      0.0235922000
_diffrn_orient_matrix_UB_31      0.0514983000
_diffrn_orient_matrix_UB_32      0.0908318000
_diffrn_orient_matrix_UB_33      -0.0677449000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            32532
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.916
_diffrn_reflns_theta_min         3.644
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50930
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2555 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         5580
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0363P)^2^+0.2614P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0686
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                5550
_reflns_number_total             5580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np1c00327_si_002.cif
_cod_data_source_block           20181108_lmt_3_64_5
_cod_database_code               1564805
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.909
_shelx_estimated_absorpt_t_min   0.804
_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:
 C17(H17), C21(H21), C4(H4A), C5(H5), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C19(H19A,H19B), C20(H20A,H20B), C15(H15A,H15B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C27(H27A,H27B,H27C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C1(H1A,H1B,H1C), C30(H30A,
 H30B,H30C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), 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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.672
_oxdiff_exptl_absorpt_empirical_full_min 0.597