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_4129189
_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         'C10 H10 Br N O'
_chemical_formula_sum            'C10 H10 Br N O'
_chemical_formula_weight         240.10
_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   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 96.901(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.8070(2)
_cell_length_b                   7.0174(2)
_cell_length_c                   14.3984(6)
_cell_measurement_reflns_used    15678
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.06
_cell_measurement_theta_min      3.09
_cell_volume                     482.18(3)
_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 0.996
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8380
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         75.455
_diffrn_reflns_theta_min         3.092
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    5.468
_exptl_absorpt_correction_T_max  0.0516
_exptl_absorpt_correction_T_min  0.0138
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'STOE LANA, absorption correction by scaling of reflection intensities.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details
; 
 Flack x determined using 644 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.005(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         1728
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0235
_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^)+(0.0466P)^2^+0.1201P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.607
_reflns_Friedel_fraction_full    0.757
_reflns_Friedel_fraction_max     0.718
_reflns_number_gt                1725
_reflns_number_total             1728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09301_si_002.cif
_cod_data_source_block           ZZJLacBr
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4129189
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.439
_shelx_estimated_absorpt_t_max   0.772
_shelx_res_checksum              74453
_shelx_hkl_checksum              45324