Transfer-catalyst-free biomimetic asymmetric reduction of 3-sulfonyl coumarins with a regenerable NAD(P)H model.
Zhu, Zhou-Hao; Ding, Yi-Xuan; Zhou, Yong-Gui; Chemical communications (Cambridge, England) 58 (2022) 3973–3976; doi:10.1039/d1cc06896b

data_7129781
_publ_section_title
;
 Transfer-catalyst-free biomimetic asymmetric reduction of 3-sulfonyl
 coumarins with a regenerable NAD(P)H model.
;
_journal_issue                   24
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              3973
_journal_page_last               3976
_journal_paper_doi               10.1039/d1cc06896b
_journal_volume                  58
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H17 F O4 S'
_chemical_formula_weight         396.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2021-03-11 deposited with the CCDC.	2022-02-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.1170(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3425(2)
_cell_length_b                   24.9386(7)
_cell_length_c                   9.4740(3)
_cell_measurement_reflns_used    9950
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      54.289
_cell_measurement_theta_min      4.651
_cell_volume                     1946.17(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            20019
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.473
_exptl_absorpt_coefficient_mu    0.201
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6411
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details
; 
 Flack x determined using 2944 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.020(18)
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         7567
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0333
_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^)+(0.0432P)^2^+0.1616P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.951
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                6742
_reflns_number_total             7567
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06896b2.cif
_cod_data_source_block           mo_d8v21165_0m
_cod_depositor_comments          'Adding full bibliography for 7129781.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129781
_shelx_estimated_absorpt_t_min   0.961
_shelx_estimated_absorpt_t_max   0.976
_shelxl_version_number           2013-4
_shelx_res_checksum              97677
_shelx_hkl_checksum              67461