Ophiobolin-Type Sesterterpenoids from the Mangrove Endophytic Fungus <i>Aspergillus</i> sp. ZJ-68.
Cai, Runlin; Jiang, Hongming; Mo, Yaling; Guo, Huixian; Li, Chunyuan; Long, Yuhua; Zang, Zhenming; She, Zhigang; Journal of natural products 82 (2019) 2268–2278; doi:10.1021/acs.jnatprod.9b00462

data_1552610
_publ_section_title
;
 Ophiobolin-Type Sesterterpenoids from the Mangrove Endophytic Fungus
 <i>Aspergillus</i> sp. ZJ-68.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2268
_journal_page_last               2278
_journal_paper_doi               10.1021/acs.jnatprod.9b00462
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C25 H34 O3'
_chemical_formula_sum            'C25 H34 O3'
_chemical_formula_weight         382.52
_chemical_melting_point          376.2
_chemical_name_common            'asperophiobolin I'
_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             2019-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.079(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.5459(5)
_cell_length_b                   21.2382(10)
_cell_length_c                   13.5497(5)
_cell_measurement_reflns_used    3297
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      73.5970
_cell_measurement_theta_min      4.1750
_cell_volume                     2171.49(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.908
_diffrn_measured_fraction_theta_max 0.858
_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     -1.00  30.00   0.50    5.00    --    0.00  19.00  90.00   62
  2  \w    -17.00  30.00   0.50    5.00    --    0.00 -82.00 -60.00   94
  3  \w     32.00  75.00   0.50    5.00    --    0.00  19.00  90.00   86
  4  \w     51.00  79.00   0.50   25.00    --   95.20 -77.00 120.00   56
  5  \w     92.00 168.00   0.50   25.00    --   95.20  82.00 150.00  152
  6  \w     38.00 115.00   0.50   25.00    --   95.20 -45.00 150.00  154
  7  \w    100.00 125.00   0.50   25.00    --   95.20 -77.00 120.00   50
  8  \w     10.00  98.00   0.50   25.00    --   95.20 -45.00-120.00  176
  9  \w     37.00  99.50   0.50   25.00    --   95.20 -45.00   0.00  125
;
_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      -0.0047352000
_diffrn_orient_matrix_UB_12      0.0164446000
_diffrn_orient_matrix_UB_13      -0.1107060000
_diffrn_orient_matrix_UB_21      0.1863036000
_diffrn_orient_matrix_UB_22      0.0292042000
_diffrn_orient_matrix_UB_23      0.0083352000
_diffrn_orient_matrix_UB_31      0.0833658000
_diffrn_orient_matrix_UB_32      -0.0643300000
_diffrn_orient_matrix_UB_33      -0.0245302000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.905
_diffrn_reflns_Laue_measured_fraction_max 0.860
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7389
_diffrn_reflns_point_group_measured_fraction_full 0.774
_diffrn_reflns_point_group_measured_fraction_max 0.572
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         74.008
_diffrn_reflns_theta_min         3.871
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_description       needle
_exptl_crystal_F_000             830
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.043
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.150
_refine_ls_abs_structure_details
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         5054
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      2.044
_refine_ls_R_factor_all          0.1693
_refine_ls_R_factor_gt           0.1624
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4338
_refine_ls_wR_factor_ref         0.4407
_reflns_Friedel_coverage         0.297
_reflns_Friedel_fraction_full    0.621
_reflns_Friedel_fraction_max     0.270
_reflns_number_gt                4488
_reflns_number_total             5054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np9b00462_si_002.cif
_cod_data_source_block           cairunlin_j-5_collect
_cod_depositor_comments
;

2022-05-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        2171.48(13)
_cod_original_formula_moiety     '2(C25 H34 O3)'
_cod_original_formula_sum        'C50 H68 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     765.04
_cod_database_code               1552610
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.821
_reflns_odcompleteness_completeness 99.73
_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
2.a Ternary CH refined with riding coordinates:
 C15'(H15'), C2(H2), C18'(H18'), C10'(H10'), C14'(H14'), C6'(H6'), C18(H18),
 C2'(H2'), C6(H6), C14(H14), C15(H15), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C13(H13C,H13D), C1'(H1'A,H1'B), C9(H9A,H9B), C12(H12C,H12D),
 C13'(H13A,H13B), C12'(H12A,H12B), C9'(H9'A,H9'B)
2.c Aromatic/amide H refined with riding coordinates:
 C16'(H16'), C4'(H4'), C17(H17), C8(H8), C8'(H8'), C16(H16), C17'(H17'),
 C21(H21), C4(H4), C21'(H21')
2.d Idealised Me refined as rotating group:
 C20(H20D,H20E,H20F), C23'(H23A,H23B,H23C), C20'(H20A,H20B,H20C), C22'(H22A,
 H22B,H22C), C25'(H25A,H25B,H25C), C24'(H24A,H24B,H24C), C25(H25D,H25E,H25F),
 C22(H22D,H22E,H22F), C24(H24D,H24E,H24F), C23(H23D,H23E,H23F)
;
_shelx_res_checksum              9967
_shelx_hkl_checksum              16940
_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 1.803
_oxdiff_exptl_absorpt_empirical_full_min 0.562