Chirality-Economy Catalysis: Asymmetric Transfer Hydrogenation of Ketones by Ru-Catalysts of Minimal Stereogenicity
Chen, Fumin; He, Dongxu; Chen, Li; Chang, Xiaoyong; Wang, David Zhigang; Xu, Chen; Xing, Xiangyou; ACS Catalysis 9 (2019) 5562–; doi:10.1021/acscatal.9b01535

data_4514419
_publ_section_title
;
 Chirality-Economy Catalysis: Asymmetric Transfer Hydrogenation of Ketones
 by Ru-Catalysts of Minimal Stereogenicity
;
_journal_issue                   6
_journal_name_full               'ACS Catalysis'
_journal_page_first              5562
_journal_paper_doi               10.1021/acscatal.9b01535
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C12 H10 I N O'
_chemical_formula_sum            'C12 H10 I N O'
_chemical_formula_weight         311.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.020(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.0930(13)
_cell_length_b                   9.8036(6)
_cell_length_c                   6.9586(6)
_cell_measurement_reflns_used    4948
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.504
_cell_measurement_theta_min      2.531
_cell_volume                     1096.33(15)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTO 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTO 100 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2477
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.583
_diffrn_reflns_theta_min         3.759
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.892
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 16067 reflections, Rint = 0.0617
 (13919 with I > 3sig(I), Rint = 0.0617)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.885
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.843
_refine_diff_density_min         -1.189
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       0.030(2)
_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   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2477
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.107
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0253
_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^)+(0.0380P)^2^+0.5524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2431
_reflns_number_total             2477
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01535_si_002.cif
_cod_data_source_block           cxy0638
_cod_depositor_comments
'Adding full bibliography for 4514419--4514420.cif.'
_cod_database_code               4514419
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.488
_shelx_estimated_absorpt_t_min   0.376
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5915(11)
 0.4085(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C6(H6)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
4.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'