Selective covalent targeting of SARS-CoV-2 main protease by enantiopure chlorofluoroacetamide.
Yamane, Daiki; Onitsuka, Satsuki; Re, Suyong; Isogai, Hikaru; Hamada, Rui; Hiramoto, Tadanari; Kawanishi, Eiji; Mizuguchi, Kenji; Shindo, Naoya; Ojida, Akio; Chemical science 13 (2022) 3027–3034; doi:10.1039/d1sc06596c

data_1566406
_publ_section_title
;
 Selective covalent targeting of SARS-CoV-2 main protease by enantiopure
 chlorofluoroacetamide.
;
_journal_issue                   10
_journal_name_full               'Chemical science'
_journal_page_first              3027
_journal_page_last               3034
_journal_paper_doi               10.1039/d1sc06596c
_journal_volume                  13
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H11 Cl F N O2'
_chemical_formula_sum            'C10 H11 Cl F N O2'
_chemical_formula_weight         231.65
_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             2021-07-28
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-11-26 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1224(2)
_cell_length_b                   8.2680(3)
_cell_length_c                   24.1637(10)
_cell_measurement_reflns_used    6715
_cell_measurement_temperature    110
_cell_measurement_theta_max      30.3680
_cell_measurement_theta_min      2.9270
_cell_volume                     1023.38(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      110
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_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     32.00  93.00   0.50    0.50    --    5.00  45.00 120.00  122
  2  \w     22.00  74.00   0.50    0.50    --  -10.00  45.00   0.00  104
  3  \w    -99.00 -42.00   0.50    0.50    --  -10.00  45.00   0.00  114
  4  \w      7.00  34.00   0.50    0.50    --  -10.20  45.00  60.00   54
  5  \w     46.00  77.00   0.50    0.50    --  -10.20  45.00  60.00   62
  6  \w    -84.00 -20.00   0.50    0.50    --  -10.20  45.00  60.00  128
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0077846000
_diffrn_orient_matrix_UB_12      0.0022872000
_diffrn_orient_matrix_UB_13      -0.0293045000
_diffrn_orient_matrix_UB_21      0.0178571000
_diffrn_orient_matrix_UB_22      0.0850376000
_diffrn_orient_matrix_UB_23      0.0009527000
_diffrn_orient_matrix_UB_31      0.1370151000
_diffrn_orient_matrix_UB_32      -0.0114363000
_diffrn_orient_matrix_UB_33      0.0014341000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            9089
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.604
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_exptl_absorpt_coefficient_mu    0.366
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_description       prism
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.409
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.138
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0247
_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^)+(0.0250P)^2^+0.3103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0598
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2279
_reflns_number_total             2351
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc06596c2.cif
_cod_data_source_block           ns-15-054b
_cod_depositor_comments
'Adding full bibliography for 1566406--1566407.cif.'
_cod_database_code               1566406
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2A), C6(H6), C3(H3), C4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              85647
_shelx_hkl_checksum              3621
_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 1.148
_oxdiff_exptl_absorpt_empirical_full_min 0.862