(±)-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_7158466
_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         'C21 H22 O8'
_chemical_formula_sum            'C21 H22 O8'
_chemical_formula_weight         402.38
_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   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                85.4988(12)
_cell_angle_beta                 85.9500(14)
_cell_angle_gamma                88.2776(15)
_cell_formula_units_Z            4
_cell_length_a                   4.53147(10)
_cell_length_b                   14.6487(2)
_cell_length_c                   28.5217(4)
_cell_measurement_reflns_used    17086
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      73.5280
_cell_measurement_theta_min      3.0090
_cell_volume                     1882.15(6)
_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      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.966
_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    -14.00  38.00   0.50    0.50    --   12.00  71.00 -70.39  104
  2  \w    -43.00  54.00   0.50    0.50    --   32.00 -55.00-174.28  194
  3  \w     14.00  46.00   0.50    0.50    --   40.00  72.00  13.53   64
  4  \w    100.00 127.00   0.50    0.50    --   40.00  72.00  13.53   54
  5  \w     25.00  78.00   0.50    1.00    --   48.00  72.00 -77.24  106
  6  \w    112.00 137.00   0.50    1.00    --   48.00  72.00 -77.24   50
  7  \w     29.00  55.00   0.50    1.00    --   56.00  73.00  52.88   52
  8  \w     94.00 121.00   0.50    1.00    --   56.00  72.00  88.61   54
  9  \w     29.00  55.00   0.50    1.00    --   56.00  72.00  88.61   52
 10  \w     29.00 104.00   0.50    1.00    --   56.00  73.00-140.54  150
 11  \w    106.00 145.00   0.50    1.00    --   56.00  73.00-140.54   78
 12  \w     32.00  61.00   0.50    1.00    --   60.00  74.00 164.91   58
 13  \w     32.00  57.00   0.50    1.00    --   60.00  74.00 143.19   50
 14  \w     32.00  59.00   0.50    1.00    --   60.00  75.00 105.93   54
 15  \w     36.00  75.00   0.50    1.00    --   64.00  74.00  73.59   78
 16  \w     37.00  72.00   0.50    1.00    --   64.00  75.00   4.37   70
 17  \w     46.00  72.00   0.50    1.00    --   72.00  73.00-178.42   52
 18  \w     44.00  87.00   0.50    1.00    --   72.00  74.00 131.32   86
 19  \w     44.00  70.00   0.50    1.00    --   72.00  75.00 -59.34   52
 20  \w     44.00  70.00   0.50    1.00    --   72.00  74.00  92.34   52
 21  \w     49.00  75.00   0.50    1.00    --   76.00  71.00 158.10   52
 22  \w     48.00  82.00   0.50    1.00    --   76.00  75.00 -36.68   68
 23  \w     57.00 100.00   0.50    1.00    --   84.00  73.00  95.84   86
 24  \w    136.00 171.00   0.50    1.00    --   84.00  73.00  95.84   70
 25  \w     69.00 117.00   0.50    1.00    --   94.60  69.00 -60.57   96
 26  \w     45.00 125.00   0.50    1.00    --   94.60 -82.00 -60.00  160
 27  \w    140.00 181.00   0.50    1.00    --   94.60  45.00 -90.00   82
 28  \w     69.00 174.00   0.50    1.00    --   94.60  68.00 -19.24  210
 29  \w     75.00 122.00   0.50    1.00    --   94.60  45.00 -90.00   94
 30  \w    147.00 173.00   0.50    1.00    --   94.60  62.00  10.40   52
 31  \w    124.00 179.00   0.50    1.00    --   94.60  74.00 155.96  110
 32  \w     66.00 121.00   0.50    1.00    --   94.60  75.00 170.69  110
 33  \w     75.00 117.00   0.50    1.00    --   94.60  62.00  10.40   84
 34  \w    148.00 175.00   0.50    1.00    --   94.60  45.00 120.00   54
 35  \w     66.00 100.00   0.50    1.00    --   94.60  74.00 155.96   68
 36  \w     45.00 119.00   0.50    1.00    --   94.60 -77.00   0.00  148
 37  \w    140.00 178.00   0.50    1.00    --   94.60  61.00  46.85   76
 38  \w    142.00 184.00   0.50    1.00    --   94.60  61.00  60.00   84
 39  \w     72.00  98.00   0.50    1.00    --   94.60  61.00  60.00   52
 40  \w     71.00 126.00   0.50    1.00    --   94.60  61.00-150.00  110
 41  \w     71.00 135.00   0.50    1.00    --   94.60  61.00  46.85  128
 42  \w    147.00 182.00   0.50    1.00    --   94.60  57.00 131.82   70
 43  \w     78.00 142.00   0.50    1.00    --   94.60  57.00 131.82  128
 44  \w     78.00 126.00   0.50    1.00    --   94.60 -82.00 150.00   96
 45  \w     71.00 182.00   0.50    1.00    --   94.60  61.00  30.00  222
 46  \w     83.00 143.00   0.50    1.00    --   94.60  45.00 120.00  120
 47  \w     71.00 168.00   0.50    1.00    --   94.60  61.00 -30.00  194
 48  \w      5.00  57.00   0.50    1.00    --   94.60 -82.00 150.00  104
 49  \w     67.00 148.00   0.50    1.00    --   94.60  73.00 -91.28  162
 50  \w    140.00 179.00   0.50    1.00    --   94.60  75.00 170.69   78
 51  \w     76.00 109.00   0.50    1.00    --   94.60 -82.00-150.00   66
 52  \w     71.00 159.00   0.50    1.00    --   94.60  60.00-128.18  176
 53  \w      9.00 125.00   0.50    1.00    --   94.60 -82.00  90.00  232
 54  \w     35.00 114.00   0.50    1.00    --   94.60 -61.00  90.00  158
;
_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      -0.0092741000
_diffrn_orient_matrix_UB_12      -0.1027649000
_diffrn_orient_matrix_UB_13      -0.0077092000
_diffrn_orient_matrix_UB_21      0.0613672000
_diffrn_orient_matrix_UB_22      -0.0239488000
_diffrn_orient_matrix_UB_23      0.0520300000
_diffrn_orient_matrix_UB_31      -0.3352272000
_diffrn_orient_matrix_UB_32      0.0011044000
_diffrn_orient_matrix_UB_33      0.0135218000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            39721
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.327
_diffrn_reflns_theta_min         3.027
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24065
_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_density_diffrn    1.420
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         7433
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0800P)^2^+1.3664P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1604
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6500
_reflns_number_total             7433
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob02006d2.cif
_cod_data_source_block           20201229_za-39
_cod_depositor_comments
'Adding full bibliography for 7158459--7158466.cif.'
_cod_original_cell_volume        1882.16(6)
_cod_database_code               7158466
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.710
_reflns_odcompleteness_completeness 99.29
_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:
 C8(H8), C9(H9), C10(H10), C8A(H8A), C9A(H9A), C10A(H10A)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C11A(H11C,H11D), C18A(H18C,H18D)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C5A(H5A), C7A(H7A)
2.d Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C2"(H2"A,H2"B,H2"C), C17(H17A,H17B,H17C), C19(H19A,H19B,
 H19C), C1B(H1BA,H1BB,H1BC), C1C(H1CA,H1CB,H1CC), C17A(H17D,H17E,H17F),
 C19A(H19D,H19E,H19F)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2A)
;
_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 2.857
_oxdiff_exptl_absorpt_empirical_full_min 0.343