Naphtho-γ-pyrone Dimers from an Endozoic <i>Aspergillus niger</i> and the Effects of Coisolated Monomers in Combination with Cisplatin on a Cisplatin-Resistant A549 Cell Line.
Hu, Yun-Wei; Liu, Ying; Guo, Er-Yan; Wang, Yu-Ying; Xu, Wan-Qi; Gao, Yan; Jiang, Xue-Yang; Feng, Feng; Xu, Jian; Liu, Wen-Yuan; Journal of natural products  (2021) –; doi:10.1021/acs.jnatprod.0c01262

data_1563709
_publ_section_title
;
 Naphtho-\g-pyrone Dimers from an Endozoic <i>Aspergillus niger</i> and
 the Effects of Coisolated Monomers in Combination with Cisplatin on a
 Cisplatin-Resistant A549 Cell Line.
;
_journal_name_full               'Journal of natural products'
_journal_paper_doi               10.1021/acs.jnatprod.0c01262
_journal_year                    2021
_chemical_formula_moiety         'C20 H12 O8, 2(H2 O)'
_chemical_formula_sum            'C20 H16 O10'
_chemical_formula_weight         416.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                101.320(15)
_cell_angle_beta                 93.023(16)
_cell_angle_gamma                99.194(15)
_cell_formula_units_Z            2
_cell_length_a                   7.160(3)
_cell_length_b                   9.102(4)
_cell_length_c                   13.073(6)
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    150
_cell_measurement_theta_max      23.733
_cell_measurement_theta_min      2.317
_cell_volume                     821.5(6)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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_temperature      150.0
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.1366
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7396
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.055
_diffrn_reflns_theta_max         25.055
_diffrn_reflns_theta_min         2.317
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.138
_exptl_absorpt_correction_T_max  0.0912
_exptl_absorpt_correction_T_min  0.0656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0762 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.7193. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.852
_refine_ls_R_factor_all          0.1851
_refine_ls_R_factor_gt           0.1235
_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^)+(0.1412P)^2^+30.3850P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3286
_refine_ls_wR_factor_ref         0.3766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1715
_reflns_number_total             2857
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01262_si_001.cif
_cod_data_source_block           n_0m
_cod_database_code               1563709
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.993
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.872(4)
 0.128(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3.a Free rotating group:
 O8(H8C,H8D), O10(H10A,H10B)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C1(H1), C3(H3A), C17(H17), C19(H19)
3.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O7(H7), O3(H3), O9(H9), O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'