(±)-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_7158460
_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         'C21 H22 O8'
_chemical_formula_sum            'C21 H22 O8'
_chemical_formula_weight         402.38
_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             2021-04-23
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   4.5507(10)
_cell_length_b                   17.161(4)
_cell_length_c                   48.011(10)
_cell_measurement_reflns_used    9704
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      49.71
_cell_measurement_theta_min      2.37
_cell_volume                     3749.4(14)
_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    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -54
_diffrn_reflns_number            53389
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        50.666
_diffrn_reflns_theta_max         50.666
_diffrn_reflns_theta_min         1.601
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.7498
_exptl_absorpt_correction_T_min  0.6651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1566 before and 0.0754 after correction. 
The Ratio of minimum to maximum transmission is 0.8870. 
The \l/2 correction factor is Not present. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       needle
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         5725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0461
_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^)+(0.0559P)^2^+1.6945P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                4872
_reflns_number_total             5725
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02006d2.cif
_cod_data_source_block           210324a_0m
_cod_depositor_comments
'Adding full bibliography for 7158459--7158466.cif.'
_cod_database_code               7158460
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.943
_olex2_refinement_description
; 
1. Twinned data refinement 
 Scales: 0.7(3) 
 0.3(3) 
2. 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 
3.a Ternary CH refined with riding coordinates: 
 C9A(H9A), C10A(H10A), C8A(H8A), C8(H8), C9(H9), C10(H10) 
3.b Secondary CH2 refined with riding coordinates: 
 C18A(H18A,H18B), C11A(H11A,H11B), C18(H18C,H18D), C11(H11C,H11D) 
3.c Aromatic/amide H refined with riding coordinates: 
 C5A(H5A), C7A(H7A), C7(H7), C5(H5) 
3.d Idealised Me refined as rotating group: 
 C19A(H19A,H19B,H19C), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,H2BC), C17A(H17A, 
 H17B,H17C), C19(H19D,H19E,H19F), C1'(H1'A,H1'B,H1'C), C17(H17D,H17E,H17F), 
 C2'(H2'A,H2'B,H2'C) 
3.e Idealised tetrahedral OH refined as rotating group: 
 O2A(H2A), O2(H2) 
;
_shelx_res_checksum              77152
_olex2_submission_special_instructions 'No special instructions were received'