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_4129191
_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         'C30 H26 N6 Ru, 2(B F4), C2 H3 N'
_chemical_formula_sum            'C32 H29 B2 F8 N7 Ru'
_chemical_formula_weight         786.31
_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
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 98.157(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3443(3)
_cell_length_b                   9.1680(2)
_cell_length_c                   21.3184(9)
_cell_measurement_reflns_used    44745
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.97
_cell_measurement_theta_min      4.19
_cell_volume                     1614.37(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 0.992
_diffrn_measured_fraction_theta_max 0.982
_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  0.1102
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            47544
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         75.779
_diffrn_reflns_theta_min         4.190
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    4.667
_exptl_absorpt_correction_T_max  0.4126
_exptl_absorpt_correction_T_min  0.0258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'STOE LANA, absorption correction by scaling of reflection intensities.'
_exptl_crystal_colour            red-orange
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.777
_refine_diff_density_min         -1.078
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details
; 
 Flack x determined using 2439 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.005(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     502
_refine_ls_number_reflns         6575
_refine_ls_number_restraints     185
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0543
_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^)+(0.1036P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1365
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                5786
_reflns_number_total             6575
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09301_si_004.cif
_cod_data_source_block           ZZJRuH
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129191
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.317
_shelx_estimated_absorpt_t_max   0.835
_shelx_res_checksum              23634
_shelx_hkl_checksum              24244