Non-C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient Enantioselective Intramolecular C(sp3)‒H Amidation
Zhou, Zijun; Chen, Shuming; Hong, Yubiao; Winterling, Erik; Tan, Yuqi; Hemming, Marcel; Harms, Klaus; Houk, K. N.; Meggers, Eric; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b09301

data_4129190
_publ_section_title
;
 Non-C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient
 Enantioselective Intramolecular C(sp3)--H Amidation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b09301
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C37 H34 N5 O2 Ru S, F6 P, C H2 Cl2'
_chemical_formula_sum            'C38 H36 Cl2 F6 N5 O2 P Ru S'
_chemical_formula_weight         943.72
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.4873(1)
_cell_length_b                   13.4873(1)
_cell_length_c                   42.0533(3)
_cell_measurement_reflns_used    121299
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.20
_cell_measurement_theta_min      3.44
_cell_volume                     7649.80(10)
_computing_cell_refinement       'X-Area Recipe 1.33.0.0 (STOE, 2015)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.127.0 (STOE, 2016)'
_computing_data_reduction
'X-Area Integrate 1.71.0.0 (STOE, 2016) X-Area LANA 1.68.2.0 (STOE, 2016)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact)'
_computing_publication_material  'X-Area 1.77'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'XT V2014/1 (Bruker AXS Inc., 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.81
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            119089
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         75.939
_diffrn_reflns_theta_min         3.441
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    6.142
_exptl_absorpt_correction_T_max  0.4100
_exptl_absorpt_correction_T_min  0.1056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'STOE LANA, absorption correction by scaling of reflection intensities.'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       nugget
_exptl_crystal_F_000             3824
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
; 
 Flack x determined using 2934 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.025(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         7924
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0280
_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^)+(0.0479P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0717
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                7340
_reflns_number_total             7924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09301_si_003.cif
_cod_data_source_block           Ru1aux
_cod_original_cell_volume        7649.80(13)
_cod_database_code               4129190
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.459
_shelx_estimated_absorpt_t_max   0.709
_shelx_res_checksum              79380
_shelx_hkl_checksum              85505