Chiral and Regenerable NAD(P)H Models Enabled Biomimetic Asymmetric Reduction: Design, Synthesis, Scope and Mechanistic Studies.
Wang, Jie; Zhao, Zi-Biao; Zhao, Yanan; Luo, Gen; Zhu, Zhou-Hao; Luo, Yi; Zhou, Yong-Gui; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b03054

data_4037775
_publ_section_title
;
 Chiral and Regenerable NAD(P)H Models Enabled Biomimetic Asymmetric
 Reduction: Design, Synthesis, Scope and Mechanistic Studies.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03054
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H17 N O'
_chemical_formula_weight         335.38
_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
_cell_angle_alpha                90
_cell_angle_beta                 103.2910(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.5211(3)
_cell_length_b                   7.4342(3)
_cell_length_c                   12.6425(5)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      140.294
_cell_measurement_theta_min      7.185
_cell_volume                     870.89(6)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            18037
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.959
_diffrn_reflns_theta_min         7.199
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.4549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
; 
 Flack x determined using 1322 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.21(11)
_refine_ls_extinction_coef       0.145(14)
_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   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2998
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0400
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0984P)^2^+0.0202P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1128
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                2947
_reflns_number_total             2998
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03054_si_003.cif
_cod_data_source_block           cu_d8v18023_0m
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4037775
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.931
_shelxl_version_number           2013-4
_shelx_res_checksum              54888
_shelx_hkl_checksum              2208