Asperunguisins A-F, Cytotoxic Asperane Sesterterpenoids from the Endolichenic Fungus Aspergillus unguis.
Li, Yue-Lan; Gao, Yun; Liu, Chun-Yu; Sun, Chun-Jing; Zhao, Zun-Tian; Lou, Hong-Xiang; Journal of natural products 82 (2019) 1527–1534; doi:10.1021/acs.jnatprod.8b01066

data_1552676
_publ_section_title
;
 Asperunguisins A-F, Cytotoxic Asperane Sesterterpenoids from the
 Endolichenic Fungus Aspergillus unguis.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1527
_journal_page_last               1534
_journal_paper_doi               10.1021/acs.jnatprod.8b01066
_journal_volume                  82
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         C25H40O3
_chemical_formula_sum            'C26 H41 Cl3 O3'
_chemical_formula_weight         507.94
_chemical_name_common            Au-46
_chemical_name_systematic
(1S,3aS,3bR,5S,5aS,6S,7R,8R,10aR,10bS)-1-isopropyl-3a,5a,8,10b-tetramethyl-1,2,3,3a,3b,4,5,5a,6,7,8,9,10,10a,10b,11-hexadecahydro-6,8-epoxycyclohepta[a]cyclopenta[f]naphthalene-5,7-diol
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6111(3)
_cell_length_b                   14.1236(6)
_cell_length_c                   25.2600(12)
_cell_measurement_reflns_used    4908
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      136.098
_cell_measurement_theta_min      6.999
_cell_volume                     2715.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1307
_diffrn_reflns_av_unetI/netI     0.0922
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            20386
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.585
_diffrn_reflns_theta_max         66.585
_diffrn_reflns_theta_min         3.499
_exptl_absorpt_coefficient_mu    3.240
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_description       needle
_exptl_crystal_F_000             1088
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details
;
 Flack x determined using 1119 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.077(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4764
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0581
_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^)+(0.0107P)^2^+2.4878P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1209
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3567
_reflns_number_total             4764
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b01066_si_003.cif
_cod_data_source_block           cu_20180124_0m_a
_cod_database_code               1552676
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              29821
_shelx_hkl_checksum              64878