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_1560802
_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'
_chemical_formula_sum            'C30 H28 O10'
_chemical_formula_weight         548.52
_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     dual
_audit_creation_date             2019-12-26
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3810(2)
_cell_length_b                   9.3907(2)
_cell_length_c                   32.0572(6)
_cell_measurement_reflns_used    8609
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.8180
_cell_measurement_theta_min      4.8990
_cell_volume                     2523.01(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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_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 0.988
_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  90.00  176
  2  \w     24.00  98.00   1.00    1.00    --   40.98-126.00   0.00   74
  3  \w     35.00 137.00   1.00    1.00    --  107.58 -61.00  60.00  102
  4  \w     79.00 178.00   1.00    1.00    --  107.58  30.00-120.00   99
  5  \w     75.00 178.00   1.00    1.00    --  107.58  77.00-180.00  103
  6  \w     94.00 164.00   1.00    1.00    --  107.58 126.00-120.00   70
  7  \w     94.00 165.00   1.00    1.00    --  107.58 126.00 120.00   71
  8  \w    124.00 151.00   1.00    1.00    --  107.58 126.00-180.00   27
  9  \w     50.00 120.00   1.00    1.00    --  107.58-126.00 -30.00   70
;
_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      0.0595274000
_diffrn_orient_matrix_UB_12      0.0931624000
_diffrn_orient_matrix_UB_13      -0.0363951000
_diffrn_orient_matrix_UB_21      -0.1724182000
_diffrn_orient_matrix_UB_22      0.0149934000
_diffrn_orient_matrix_UB_23      -0.0159841000
_diffrn_orient_matrix_UB_31      -0.0221004000
_diffrn_orient_matrix_UB_32      0.1343190000
_diffrn_orient_matrix_UB_33      0.0269889000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            12017
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.922
_diffrn_reflns_theta_min         2.757
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.912
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41804
_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    1.444
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details
;
 Flack x determined using 1942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_coef       0.0063(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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         4991
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0313
_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^)+(0.0455P)^2^+0.3047P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0848
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.954
_reflns_number_gt                4856
_reflns_number_total             4991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np0c01136_si_002.cif
_cod_data_source_block           z-1
_cod_database_code               1560802
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_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:
 C15(H15), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C17(H17A,H17B,H17C), C22(H22A,H22B,H22C), C20(H20A,H20B,
 H20C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O10(H10), O9(H9), O3(H3), O6(H6)
;
_shelx_res_checksum              13930
_shelx_hkl_checksum              96493
_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 1.929
_oxdiff_exptl_absorpt_empirical_full_min 0.528