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_1552587
_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 O4'
_chemical_formula_sum            'C25 H36 O4'
_chemical_formula_weight         400.54
_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   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                   6.25416(8)
_cell_length_b                   14.0422(2)
_cell_length_c                   24.9184(3)
_cell_measurement_reflns_used    6068
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.3410
_cell_measurement_theta_min      3.5420
_cell_volume                     2188.39(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 0.987
_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    -32.00  31.00   0.50    0.50    --    0.00 -82.00 120.00  126
  2  \w     29.00  86.00   0.50    0.50    --    0.00  38.00 -60.00  114
  3  \w    -17.00   8.00   0.50    0.50    --    0.00 -77.00 -30.00   50
  4  \w     63.00  89.00   0.50    1.50    --   94.60 -15.00-150.00   52
  5  \w     76.00 184.00   0.50    1.50    --   94.60  45.00 150.00  216
  6  \w     57.00 111.00   0.50    1.50    --   94.60 -61.00-150.00  108
  7  \w     86.00 129.00   0.50    1.50    --   94.60  15.00 -90.00   86
  8  \w     16.00  51.00   0.50    1.50    --   94.60 -61.00-150.00   70
  9  \w     27.00 118.00   0.50    1.50    --   94.60 -61.00  30.00  182
 10  \w     19.00  60.00   0.50    1.50    --   94.60 -15.00-150.00   82
 11  \w      5.00 113.00   0.50    1.50    --   94.60 -45.00-150.00  216
;
_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      -0.0025743000
_diffrn_orient_matrix_UB_12      -0.1077867000
_diffrn_orient_matrix_UB_13      0.0115314000
_diffrn_orient_matrix_UB_21      -0.1115333000
_diffrn_orient_matrix_UB_22      -0.0177925000
_diffrn_orient_matrix_UB_23      -0.0542012000
_diffrn_orient_matrix_UB_31      0.2196254000
_diffrn_orient_matrix_UB_32      -0.0101798000
_diffrn_orient_matrix_UB_33      -0.0273955000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10972
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.799
_diffrn_reflns_theta_min         3.547
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35482
_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            block
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_description       colorless
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1537 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4310
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0575P)^2^+0.5789P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                3996
_reflns_number_total             4310
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00744_si_004.cif
_cod_data_source_block           20180913_lmt-3-22-4
_cod_original_cell_volume        2188.39(6)
_cod_database_code               1552587
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.969
_shelx_estimated_absorpt_t_min   0.832
_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. Restrained distances
 C18-C19' \\sim C18-C19
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq, Uanis(C19') \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C24) = Uanis(C24')
4. Others
 Sof(H18)=Sof(C24')=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C19')=Sof(C25')=
 Sof(H25C)=Sof(H25D)=Sof(O4')=Sof(H4')=1-FVAR(1)
 Sof(H18A)=Sof(C19)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=
 Sof(H25B)=Sof(O4)=Sof(H4A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C10(H10), C15(H15), C17(H17)
5.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,H13B),
 C16(H16A,H16B), C21(H21A,H21B), C25(H25A,H25B), C25'(H25C,H25D)
5.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C18(H18A), C18(H18)
5.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C24'(H24D,H24E,H24F)
5.e Idealised tetrahedral OH refined as rotating group:
 O2(H2A), O4(H4A), O4'(H4')
;
_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 1.795
_oxdiff_exptl_absorpt_empirical_full_min 0.397