Axial Chiral Binaphthoquinone and Perylenequinones from the Stromata of <i>Hypocrella bambusae</i> Are SARS-CoV-2 Entry Inhibitors.
Li, Yu-Ting; Yang, Chan; Wu, Yan; Lv, Jun-Jiang; Feng, Xiao; Tian, Xiaofei; Zhou, Zhengzheng; Pan, Xiaoyan; Liu, Shuwen; Tian, Li-Wen; Journal of natural products 84 (2021) 436–443; doi:10.1021/acs.jnatprod.0c01136

data_1560803
_publ_section_title
;
 Axial Chiral Binaphthoquinone and Perylenequinones from the Stromata of
 <i>Hypocrella bambusae</i> Are SARS-CoV-2 Entry Inhibitors.
;
_journal_issue                   2
_journal_name_full               'Journal of natural products'
_journal_page_first              436
_journal_page_last               443
_journal_paper_doi               10.1021/acs.jnatprod.0c01136
_journal_volume                  84
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H28 O10, O, H2 O'
_chemical_formula_sum            'C30 H32 O12'
_chemical_formula_weight         584.55
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-06-02
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.17520(13)
_cell_length_b                   17.53391(17)
_cell_length_c                   23.9821(2)
_cell_measurement_reflns_used    19867
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5210
_cell_measurement_theta_min      2.4860
_cell_volume                     5540.17(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_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   -129.00  47.00   1.00    1.00    --  -40.98   0.00  30.00  176
  2  \w     23.00  97.00   1.00    1.00    --   40.98-125.00   0.00   74
  3  \w     24.00 109.00   1.00    1.14    --  106.95 -94.00 -60.00   85
  4  \w     79.00 178.00   1.00    1.14    --  106.95  30.00 -60.00   99
  5  \w     78.00 178.00   1.00    1.14    --  106.95  61.00   0.00  100
  6  \w     94.00 178.00   1.00    1.14    --  106.95 125.00 -90.00   84
  7  \w     24.00 109.00   1.00    1.14    --  106.95 -94.00-120.00   85
  8  \w     94.00 178.00   1.00    1.14    --  106.95 125.00 -60.00   84
  9  \w     94.00 178.00   1.00    1.14    --  106.95 125.00 120.00   84
 10  \w   -117.00 -65.00   1.00    1.00    --  -40.98 -77.00   0.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0633969000
_diffrn_orient_matrix_UB_12      0.0361468000
_diffrn_orient_matrix_UB_13      0.0470587000
_diffrn_orient_matrix_UB_21      -0.0699579000
_diffrn_orient_matrix_UB_22      0.0704835000
_diffrn_orient_matrix_UB_23      -0.0005271000
_diffrn_orient_matrix_UB_31      -0.0691501000
_diffrn_orient_matrix_UB_32      -0.0378993000
_diffrn_orient_matrix_UB_33      0.0436999000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            30898
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.720
_diffrn_reflns_theta_min         3.122
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.791
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 4446 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     783
_refine_ls_number_reflns         10993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0562
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1081P)^2^+3.4474P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1644
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                10551
_reflns_number_total             10993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01136_si_003.cif
_cod_data_source_block           e2-2
_cod_original_cell_volume        5540.18(9)
_cod_database_code               1560803
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.882
_reflns_odcompleteness_completeness 99.98
_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, All O(H,H) groups
2.a Free rotating group:
 O029(H02A,H02B), O1W(H1WA,H1WB)
2.b Ternary CH refined with riding coordinates:
 C8B(H8B), C23B(H23B), C2(H2), C13(H13)
2.c Secondary CH2 refined with riding coordinates:
 C01D(H01A,H01B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C18B(H18B), C2B(H2B), C8(H8), C5(H5)
2.e Idealised Me refined as rotating group:
 C21B(H21A,H21B,H21C), C25B(H25A,H25B,H25C), C29B(H29A,H29B,H29C), C21(H21D,
 H21E,H21F), C27B(H27A,H27B,H27C), C28B(H28A,H28B,H28C), C17(H17A,H17B,H17C),
 C20(H20D,H20E,H20F), C20B(H20A,H20B,H20C), C18(H18A,H18C,H18D), C19(H19A,H19B,
 H19C), C22(H22A,H22B,H22C)
2.f Idealised tetrahedral OH refined as rotating group:
 O6B(H6B), O9B(H9B), O10B(H10B), O6(H6), O3B(H3B), O3(H3), O9(H9), O10(H10)
;
_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 1.935
_oxdiff_exptl_absorpt_empirical_full_min 0.728