Rh(I)/NHC*-Catalyzed Site- and Enantioselective Functionalization of C(sp3)–H Bonds Toward Chiral Triarylmethanes
Kim, Ju Hyun; Greßies, Steffen; Boultadakis-Arapinis, Mélissa; Daniliuc, Constantin; Glorius, Frank; ACS Catalysis 6 (2016) 7652–; doi:10.1021/acscatal.6b02392

data_4513972
_publ_section_title
;
 Rh(I)/NHC*-Catalyzed Site- and Enantioselective Functionalization of
 C(sp3)--H Bonds Toward Chiral Triarylmethanes
;
_journal_issue                   11
_journal_name_full               'ACS Catalysis'
_journal_page_first              7652
_journal_paper_doi               10.1021/acscatal.6b02392
_journal_volume                  6
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H16 Cl N'
_chemical_formula_weight         329.81
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0503(7)
_cell_length_b                   14.698(2)
_cell_length_c                   18.444(3)
_cell_measurement_reflns_used    1989
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      65.5677
_cell_measurement_theta_min      4.7953
_cell_volume                     1640.2(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 v.2014.1--1 (Bruker AXS Inc., 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL--2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'KappaCCD APEXII'
_diffrn_measurement_method       'phi / omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0740
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5732
_diffrn_reflns_theta_full        65.07
_diffrn_reflns_theta_max         65.07
_diffrn_reflns_theta_min         3.85
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.049
_exptl_absorpt_correction_T_max  0.96
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/2, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.247
_refine_ls_abs_structure_details
;
Flack x determined using 764 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.065(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.977
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0446
_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^)+(0.0544P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1111
_reflns_number_gt                2162
_reflns_number_total             2582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b02392_si_002.cif
_cod_data_source_block           glo8253
_cod_depositor_comments
'Adding full bibliography for 4513972--4513973.cif.'
_cod_database_code               4513972
_shelx_res_checksum              53164
_shelx_hkl_checksum              34760