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_1552588
_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 H36 O5'
_chemical_formula_sum            'C25 H36 O5'
_chemical_formula_weight         416.54
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-05-06
_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                   6.02890(10)
_cell_length_b                   14.1660(2)
_cell_length_c                   25.7023(2)
_cell_measurement_reflns_used    31656
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.8700
_cell_measurement_theta_min      3.4390
_cell_volume                     2195.12(5)
_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 0.995
_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    -34.00  22.00   0.50    0.50    --    0.00 -57.00  30.00  112
  2  \w     40.00  89.00   0.50    0.50    --    0.00  38.00 -90.00   98
  3  \w    -41.00  29.00   0.50    0.50    --    0.00 -77.00  90.00  140
  4  \w    -89.00 -50.00   0.50    0.50    --    0.00 -57.00  30.00   78
  5  \w     48.00  74.00   0.50    0.50    --    0.00  38.00 -60.00   52
  6  \w    -16.00  39.00   0.50    0.50    --    0.00  38.00  90.00  110
  7  \w    -17.00  21.00   0.50    0.50    --    0.00  38.00 -60.00   76
  8  \w    -17.00  67.00   0.50    0.50    --    0.00  19.00-180.00  168
  9  \w     54.00  88.00   0.50    0.50    --    0.00  38.00  90.00   68
 10  \w    -17.00  49.00   0.50    0.50    --    0.00  19.00  60.00  132
 11  \w    -17.00  33.00   0.50    0.50    --    0.00  38.00 -90.00  100
 12  \w     71.00 177.00   0.50    1.00    --   94.60  61.00-162.95  212
 13  \w     66.00  92.00   0.50    1.00    --   94.60  74.00-146.89   52
 14  \w     68.00 101.00   0.50    1.00    --   94.60  69.00 -51.62   66
 15  \w     67.00  92.00   0.50    1.00    --   94.60  73.00  46.44   50
 16  \w    154.00 180.00   0.50    1.00    --   94.60  64.00   5.68   52
 17  \w     66.00  91.00   0.50    1.00    --   94.60  74.00 114.45   50
 18  \w    123.00 149.00   0.50    1.00    --   94.60  57.00  31.43   52
 19  \w     67.00 103.00   0.50    1.00    --   94.60  72.00 132.75   72
 20  \w     70.00 140.00   0.50    1.00    --   94.60  64.00   5.68  140
 21  \w    125.00 179.00   0.50    1.00    --   94.60  73.00  95.17  108
 22  \w     71.00 103.00   0.50    1.00    --   94.60  59.00 -68.12   64
 23  \w     71.00 104.00   0.50    1.00    --   94.60  59.00 -78.04   66
 24  \w     73.00 100.00   0.50    1.00    --   94.60  55.00  44.09   54
 25  \w     69.00  94.00   0.50    1.00    --   94.60  69.00   7.07   50
 26  \w     68.00  94.00   0.50    1.00    --   94.60  70.00  83.01   52
 27  \w     71.00 184.00   0.50    1.00    --   94.60  62.00 -22.39  226
 28  \w      6.00 118.00   0.50    1.00    --   94.60 -61.00 120.00  224
 29  \w     35.00 126.00   0.50    1.00    --   94.60 -82.00 120.00  182
 30  \w     13.00  39.00   0.50    1.00    --   94.60 -82.00   0.00   52
 31  \w     67.00 119.00   0.50    1.00    --   94.60  73.00  95.17  104
 32  \w     66.00 102.00   0.50    1.00    --   94.60  74.00 144.36   72
 33  \w     72.00 178.00   0.50    1.00    --   94.60  58.00  53.38  212
 34  \w     71.00 109.00   0.50    1.00    --   94.60  61.00-150.00   76
 35  \w     68.00  94.00   0.50    1.00    --   94.60  69.00 -21.57   52
 36  \w     71.00 138.00   0.50    1.00    --   94.60  61.00 -60.00  134
 37  \w     67.00  93.00   0.50    1.00    --   94.60  73.00 -63.34   52
 38  \w     14.00 118.00   0.50    1.00    --   94.60 -61.00   0.00  208
 39  \w     69.00  95.00   0.50    1.00    --   94.60  66.00-115.99   52
 40  \w     70.00 178.00   0.50    1.00    --   94.60  63.00  79.32  216
 41  \w     71.00 184.00   0.50    1.00    --   94.60  61.00-180.00  226
 42  \w     71.00 113.00   0.50    1.00    --   94.60  61.00 -30.00   84
 43  \w    121.00 165.00   0.50    1.00    --   94.60  61.00 -30.00   88
 44  \w     72.00 183.00   0.50    1.00    --   94.60  61.00 120.00  222
 45  \w     88.00 126.00   0.50    1.00    --   94.60 -82.00 -90.00   76
 46  \w     71.00  97.00   0.50    1.00    --   94.60  61.00   0.00   52
 47  \w     71.00 174.00   0.50    1.00    --   94.60  61.00-120.00  206
 48  \w     45.00 113.00   0.50    1.00    --   94.60 -82.00   0.00  136
 49  \w    119.00 145.00   0.50    1.00    --   94.60  69.00 -51.62   52
 50  \w    132.00 157.00   0.50    1.00    --   94.60  74.00-146.89   50
 51  \w     72.00  98.00   0.50    1.00    --   94.60  62.00 169.11   52
 52  \w     72.00 114.00   0.50    1.00    --   94.60  57.00  31.43   84
 53  \w     42.00 115.00   0.50    1.00    --   94.60 -61.00-150.00  146
 54  \w     16.00  97.00   0.50    1.00    --   94.60 -82.00-120.00  162
 55  \w     70.00 142.00   0.50    1.00    --   94.60  63.00 -99.37  144
;
_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      0.0467745000
_diffrn_orient_matrix_UB_12      0.0827444000
_diffrn_orient_matrix_UB_13      -0.0373226000
_diffrn_orient_matrix_UB_21      0.0282166000
_diffrn_orient_matrix_UB_22      0.0667689000
_diffrn_orient_matrix_UB_23      0.0468804000
_diffrn_orient_matrix_UB_31      0.2495257000
_diffrn_orient_matrix_UB_32      -0.0229760000
_diffrn_orient_matrix_UB_33      0.0017081000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0963
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            49996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.128
_diffrn_reflns_theta_min         3.439
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67649
_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    1.260
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1792 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4440
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0796P)^2^+0.5961P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1200
_reflns_Friedel_coverage         0.721
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                4336
_reflns_number_total             4440
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00744_si_002.cif
_cod_data_source_block           20180830-lmt3-28-5
_cod_database_code               1552588
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.934
_shelx_estimated_absorpt_t_min   0.820
_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, All O(H,H,H) groups
2. Restrained distances
 H3B-O3 = H3A-O3
 0.8 with sigma of 0.01
 H1BB-O1
 0.8 with sigma of 0.01
 C19-C25 \\sim C19-C25'
 with sigma of 0.01
 C25-O5 \\sim C25'-O5'
 with sigma of 0.01
3. Others
 Sof(H3B)=Sof(C25')=Sof(H25C)=Sof(H25D)=Sof(O5')=Sof(H5')=Sof(H1BB)=1-FVAR(1)
 Sof(H1AA)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(O5)=Sof(H5)=Sof(H3A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C8(H8), C10(H10), C15(H15), C17(H17)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B), C16(H16A,H16B),
 C21(H21A,H21B), C25(H25A,H25B), C25'(H25C,H25D)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C18(H18)
4.d Tetrahedral OH refined with riding coordinates:
 O5(H5), O5'(H5')
4.e Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1AA)
;
_shelx_res_checksum              70601
_shelx_hkl_checksum              13178
_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 1.673
_oxdiff_exptl_absorpt_empirical_full_min 0.377