Bipolaricins A-I, Ophiobolin-Type Tetracyclic Sesterterpenes from a Phytopathogenic <i>Bipolaris</i> sp. Fungus.
Liu, Mengting; Sun, Weiguang; Shen, Ling; Hao, Xincai; Al Anbari, Weaam Hasan; Lin, Shuang; Li, Huaqiang; Gao, Weixi; Wang, Jianping; Hu, Zhengxi; Zhang, Yonghui; Journal of natural products 82 (2019) 2897–2906; doi:10.1021/acs.jnatprod.9b00744

data_1552586
_publ_section_title
;
 Bipolaricins A-I, Ophiobolin-Type Tetracyclic Sesterterpenes from a
 Phytopathogenic <i>Bipolaris</i> sp. Fungus.
;
_journal_issue                   10
_journal_name_full               'Journal of natural products'
_journal_page_first              2897
_journal_page_last               2906
_journal_paper_doi               10.1021/acs.jnatprod.9b00744
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H34 O4'
_chemical_formula_sum            'C25 H34 O4'
_chemical_formula_weight         398.52
_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             2019-01-21
_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                   7.63340(19)
_cell_length_b                   9.1599(3)
_cell_length_c                   31.7840(7)
_cell_measurement_reflns_used    28270
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.7510
_cell_measurement_theta_min      5.0160
_cell_volume                     2222.37(10)
_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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_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     -9.00  16.00   0.50    0.50    --    0.00 -38.00  90.00   50
  2  \w    -89.00 -36.00   0.50    0.50    --    0.00 -38.00   0.00  106
  3  \w    -22.00  30.00   0.50    0.50    --    0.00 -82.00 150.00  104
  4  \w    -46.00 -20.00   0.50    0.50    --    0.00 -38.00  90.00   52
  5  \w    -17.00  22.00   0.50    0.50    --    0.00  38.00 -90.00   78
  6  \w     28.00  88.00   0.50    0.50    --    0.00  38.00 -90.00  120
  7  \w      0.00  31.00   0.50    0.50    --    0.00 -82.00  90.00   62
  8  \w    -26.00  17.00   0.50    0.50    --    0.00 -38.00   0.00   86
  9  \w    -18.00  67.00   0.50    0.50    --    0.00  19.00-180.00  170
 10  \w    -46.00  21.00   0.50    0.50    --    0.00 -57.00-180.00  134
 11  \w    -10.00  82.00   0.50    0.50    --    0.00  57.00 -30.00  184
 12  \w     99.00 132.00   0.50    0.50    --   94.60  66.00 153.19   66
 13  \w     71.00  98.00   0.50    0.50    --   94.60  60.00 118.99   54
 14  \w    136.00 171.00   0.50    0.50    --   94.60  66.00 153.19   70
 15  \w     69.00  95.00   0.50    0.50    --   94.60  66.00 153.19   52
 16  \w     66.00  94.00   0.50    0.50    --   94.60  74.00 122.64   56
 17  \w     70.00 101.00   0.50    0.50    --   94.60  64.00-142.04   62
 18  \w     71.00 181.00   0.50    0.50    --   94.60  59.00 169.71  220
 19  \w     68.00  93.00   0.50    0.50    --   94.60  70.00 -20.75   50
 20  \w     73.00 183.00   0.50    0.50    --   94.60  56.00 -59.89  220
 21  \w     71.00  97.00   0.50    0.50    --   94.60  59.00  55.28   52
 22  \w    114.00 184.00   0.50    0.50    --   94.60  70.00 -20.75  140
 23  \w     66.00  91.00   0.50    0.50    --   94.60  75.00  87.78   50
 24  \w     68.00  95.00   0.50    0.50    --   94.60  70.00-139.01   54
 25  \w     69.00  95.00   0.50    0.50    --   94.60  67.00 -27.60   52
 26  \w    136.00 171.00   0.50    0.50    --   94.60  67.00 -27.60   70
 27  \w     70.00 173.00   0.50    0.50    --   94.60  64.00-107.59  206
 28  \w     73.00 132.00   0.50    0.50    --   94.60  54.00 -69.54  118
 29  \w    157.00 182.00   0.50    0.50    --   94.60  54.00 -69.54   50
 30  \w     69.00  95.00   0.50    0.50    --   94.60  66.00 145.18   52
 31  \w     72.00 183.00   0.50    0.50    --   94.60  58.00 133.12  222
 32  \w     71.00 135.00   0.50    0.50    --   94.60  62.00   9.01  128
 33  \w     68.00 113.00   0.50    0.50    --   94.60  69.00  81.64   90
 34  \w      6.00 125.00   0.50    0.50    --   94.60 -82.00-120.00  238
 35  \w    109.00 159.00   0.50    0.50    --   94.60  73.00-130.87  100
 36  \w      6.00 125.00   0.50    0.50    --   94.60 -82.00 -30.00  238
 37  \w      5.00 126.00   0.50    0.50    --   94.60 -82.00 150.00  242
 38  \w     67.00 103.00   0.50    0.50    --   94.60  73.00-130.87   72
 39  \w    145.00 170.00   0.50    0.50    --   94.60  74.00   7.27   50
 40  \w     71.00 184.00   0.50    0.50    --   94.60  61.00-169.56  226
 41  \w     28.00  74.00   0.50    0.50    --   94.60 -77.00 -60.00   92
 42  \w     94.00 119.00   0.50    0.50    --   94.60 -77.00 -60.00   50
 43  \w     71.00  97.00   0.50    0.50    --   94.60  61.00 -90.00   52
 44  \w     71.00 109.00   0.50    0.50    --   94.60  61.00   0.00   76
 45  \w    125.00 150.00   0.50    0.50    --   94.60  61.00   0.00   50
 46  \w    145.00 170.00   0.50    0.50    --   94.60  73.00 -57.52   50
 47  \w     67.00  92.00   0.50    0.50    --   94.60  73.00 -57.52   50
 48  \w     72.00  98.00   0.50    0.50    --   94.60  58.00-177.49   52
 49  \w     66.00  92.00   0.50    0.50    --   94.60  74.00   7.27   52
 50  \w     42.00  67.00   0.50    0.50    --   94.60 -82.00-180.00   50
 51  \w     93.00 122.00   0.50    0.50    --   94.60 -82.00-180.00   58
 52  \w     75.00 184.00   0.50    0.50    --   94.60  45.00  60.00  218
 53  \w     71.00  97.00   0.50    0.50    --   94.60  61.00-150.00   52
 54  \w     72.00  97.00   0.50    0.50    --   94.60  61.00 -60.00   50
 55  \w     71.00 108.00   0.50    0.50    --   94.60  61.00 -30.00   74
 56  \w     71.00  97.00   0.50    0.50    --   94.60  61.00  60.00   52
 57  \w     73.00  99.00   0.50    0.50    --   94.60  52.00-145.88   52
 58  \w     42.00 112.00   0.50    0.50    --   94.60 -82.00  60.00  140
 59  \w     79.00 106.00   0.50    0.50    --   94.60  30.00  60.00   54
 60  \w     72.00 176.00   0.50    0.50    --   94.60  55.00  81.45  208
 61  \w    156.00 182.00   0.50    0.50    --   94.60  55.00  50.58   52
 62  \w     52.00 126.00   0.50    0.50    --   94.60 -82.00  90.00  148
 63  \w     72.00  98.00   0.50    0.50    --   94.60  55.00  50.58   52
;
_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      0.0663236000
_diffrn_orient_matrix_UB_12      -0.0186926000
_diffrn_orient_matrix_UB_13      0.0454864000
_diffrn_orient_matrix_UB_21      -0.1895247000
_diffrn_orient_matrix_UB_22      -0.0248789000
_diffrn_orient_matrix_UB_23      0.0150319000
_diffrn_orient_matrix_UB_31      0.0209795000
_diffrn_orient_matrix_UB_32      -0.1652289000
_diffrn_orient_matrix_UB_33      -0.0073690000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            52303
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.381
_diffrn_reflns_theta_min         2.781
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54275
_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    1.191
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1746 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0589P)^2^+0.9178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1156
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.964
_reflns_number_gt                4332
_reflns_number_total             4473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00744_si_003.cif
_cod_data_source_block           20181128_lmt3-24-1
_cod_original_cell_volume        2222.38(10)
_cod_database_code               1552586
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.744
_reflns_odcompleteness_completeness 99.96
_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:
 C2(H2), C6(H6), C10(H10), C15(H15), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B),
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C18(H18), C21(H21)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_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 1.802
_oxdiff_exptl_absorpt_empirical_full_min 0.462