(±)-Usphenethylones A-C, three pairs of heterodimeric polyketide enantiomers from <i>Aspergillus ustus</i> 3.3904.
Peng, Xiaogang; Zhou, Shuang; Liu, Junjun; Gao, Ying; Chang, Jinling; Ruan, Hanli; Organic & biomolecular chemistry 20 (2022) 694–700; doi:10.1039/d1ob02006d

data_7158461
_publ_section_title
;
 (+-)-Usphenethylones A-C, three pairs of heterodimeric polyketide
 enantiomers from <i>Aspergillus ustus</i> 3.3904.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              694
_journal_page_last               700
_journal_paper_doi               10.1039/d1ob02006d
_journal_volume                  20
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H20 O7, H2 O'
_chemical_formula_sum            'C20 H22 O8'
_chemical_formula_weight         390.37
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-15
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) 
;
_audit_update_record
;
2021-08-20 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.280(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.126(4)
_cell_length_b                   4.5761(13)
_cell_length_c                   14.955(5)
_cell_measurement_reflns_used    8807
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      57.12
_cell_measurement_theta_min      2.80
_cell_volume                     888.0(5)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'XM  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16506
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.994
_diffrn_reflns_theta_min         2.798
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker,2016/2)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_description       needle
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details
; 
 Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0435
_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^)+(0.0733P)^2^+0.0060P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                2898
_reflns_number_total             3317
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02006d2.cif
_cod_data_source_block           210413k_0m
_cod_depositor_comments
'Adding full bibliography for 7158459--7158466.cif.'
_cod_database_code               7158461
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.942
_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) groups 
2.a Riding coordinates: 
 O8(H8C,H8D) 
2.b Ternary CH refined with riding coordinates: 
 C9(H9), C10(H10) 
2.c Secondary CH2 refined with riding coordinates: 
 C8(H8A,H8B), C11(H11A,H11B), C18(H18A,H18B) 
2.d Aromatic/amide H refined with riding coordinates: 
 C5(H5), C7(H7) 
2.e Idealised Me refined as rotating group: 
 C1'(H1'A,H1'B,H1'C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C) 
2.f Idealised tetrahedral OH refined as rotating group: 
 O2(H2) 
;
_shelx_res_checksum              57043
_olex2_submission_special_instructions 'No special instructions were received'