Amino Acid Derived Chiral Aminobenzimidazole Manganese Catalysts for Asymmetric Transfer Hydrogenation of Ketones
Wang, Lixian; Lin, Jin; Sun, Qiangsheng; Xia, Chungu; Sun, Wei; ACS Catalysis 11 (2021) 8033–8041; doi:10.1021/acscatal.1c00616

data_4518827
_publ_section_title
;
 Amino Acid Derived Chiral Aminobenzimidazole Manganese Catalysts for
 Asymmetric Transfer Hydrogenation of Ketones
;
_journal_issue                   13
_journal_name_full               'ACS Catalysis'
_journal_page_first              8033
_journal_page_last               8041
_journal_paper_doi               10.1021/acscatal.1c00616
_journal_volume                  11
_journal_year                    2021
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H19 Br Mn N3 O3'
_chemical_formula_sum            'C21 H19 Br Mn N3 O3'
_chemical_formula_weight         496.24
_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     direct
_audit_creation_date             2020-07-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.1249(10)
_cell_length_b                   18.8575(14)
_cell_length_c                   20.0527(15)
_cell_measurement_reflns_used    9015
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      24.07
_cell_measurement_theta_min      2.16
_cell_volume                     4963.1(6)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0562
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33185
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.482
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1349 before and 0.0687 after correction.
The Ratio of minimum to maximum transmission is 0.4905.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear dark yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_description       block
_exptl_crystal_F_000             2000
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.044
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.045(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         8715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0389
_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^)+(0.0445P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                7571
_reflns_number_total             8715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c00616_si_003.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 4518826--4518827.cif.'
_cod_database_code               4518827
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.671
_shelx_estimated_absorpt_t_min   0.563
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.955(11)
 0.045(11)
2. 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 C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C15(H15), C36(H36), N3(H3A), N6(H6A)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C37(H37A,H37B), C38(H38A,
 H38B), C39(H39A,H39B)
3.c Aromatic/amide H refined with riding coordinates:
 C43(H43), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C29(H29), C30(H30), C31(H31)
3.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C34(H34A,H34B,H34C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              37693
_shelx_hkl_checksum              59234
_shelx_fab_checksum              33317
_olex2_submission_special_instructions 'No special instructions were received'