(±)-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_7158464
_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_formula_moiety         'C20 H20 O7'
_chemical_formula_sum            'C20 H20 O7'
_chemical_formula_weight         372.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-11-29 deposited with the CCDC.	2021-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.5797(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.66489(13)
_cell_length_b                   15.50084(13)
_cell_length_c                   8.21733(8)
_cell_measurement_reflns_used    11825
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4640
_cell_measurement_theta_min      3.3250
_cell_volume                     1698.79(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_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    -51.00  -7.00   0.50    0.50    --    0.00 -76.00  44.00   88
  2  \w      8.00 107.00   0.50    0.50    --   94.60 -76.00  44.00  198
  3  \w     73.00 134.00   0.50    0.50    --   94.60  76.00 171.00  122
  4  \w    -25.00  29.00   0.50    0.50    --    0.00 -77.00  60.00  108
  5  \w    -29.00  27.00   0.50    0.50    --    0.00 -82.00-180.00  112
  6  \w    -25.00  27.00   0.50    0.50    --    0.00 -82.00 120.00  104
  7  \w    -20.00   6.00   0.50    0.50    --    0.00 -82.00 -90.00   52
  8  \w    -87.00  13.00   0.50    0.50    --    0.00 -19.00  60.00  200
  9  \w     98.00 181.00   0.50    0.50    --   94.60  30.00-120.00  166
 10  \w    123.00 148.00   0.50    0.50    --   94.60  82.00-150.00   50
 11  \w     78.00 184.00   0.50    0.50    --   94.60  30.00 -90.00  212
 12  \w     80.00 184.00   0.50    0.50    --   94.60  77.00 150.00  208
 13  \w     79.00 121.00   0.50    0.50    --   94.60  45.00 -30.00   84
 14  \w     15.00  65.00   0.50    0.50    --   94.60 -77.00 150.00  100
 15  \w     86.00 122.00   0.50    0.50    --   94.60 -77.00 150.00   72
 16  \w    158.00 184.00   0.50    0.50    --   94.60  82.00 120.00   52
 17  \w      9.00  58.00   0.50    0.50    --   94.60 -77.00 -30.00   98
 18  \w     47.00 117.00   0.50    0.50    --   94.60 -61.00  30.00  140
 19  \w    131.00 166.00   0.50    0.50    --   94.60  15.00 120.00   70
 20  \w     75.00 113.00   0.50    0.50    --   94.60 -77.00 -30.00   76
 21  \w      5.00  75.00   0.50    0.50    --   94.60 -30.00-120.00  140
 22  \w     89.00 119.00   0.50    0.50    --   94.60  15.00 120.00   60
 23  \w     77.00 179.00   0.50    0.50    --   94.60  45.00 -60.00  204
 24  \w    128.00 153.00   0.50    0.50    --   94.60  45.00 -30.00   50
 25  \w     86.00 112.00   0.50    0.50    --   94.60  77.00  90.00   52
 26  \w    140.00 182.00   0.50    0.50    --   94.60  82.00  90.00   84
 27  \w     79.00 104.00   0.50    0.50    --   94.60  77.00 120.00   50
 28  \w    100.00 125.00   0.50    0.50    --   94.60  82.00  90.00   50
;
_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      -0.0045959000
_diffrn_orient_matrix_UB_12      -0.0260592000
_diffrn_orient_matrix_UB_13      0.1790938000
_diffrn_orient_matrix_UB_21      -0.0676182000
_diffrn_orient_matrix_UB_22      0.0783173000
_diffrn_orient_matrix_UB_23      0.0111543000
_diffrn_orient_matrix_UB_31      -0.0935387000
_diffrn_orient_matrix_UB_32      -0.0553797000
_diffrn_orient_matrix_UB_33      -0.0684695000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            19485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.925
_diffrn_reflns_theta_min         3.314
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.928
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3396
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0332
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+0.7800P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3166
_reflns_number_total             3396
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02006d2.cif
_cod_data_source_block           20201225_za-34
_cod_depositor_comments
'Adding full bibliography for 7158459--7158466.cif.'
_cod_database_code               7158464
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.913
_shelx_estimated_absorpt_t_min   0.768
_reflns_odcompleteness_completeness 100.00
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
2.d Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 2.638
_oxdiff_exptl_absorpt_empirical_full_min 0.630