N-Methylation of ortho-substituted aromatic amines with methanol catalyzed by 2-arylbenzo[d]oxazole NHC-Ir(iii) complexes.
Huang, Shuang; Hong, Xi; Cui, He-Zhen; Zhou, Quan; Lin, Yue-Jian; Hou, Xiu-Feng; Dalton transactions (Cambridge, England : 2003) 48 (2019) 5072–5082; doi:10.1039/c9dt00218a

data_7049262
_publ_section_title
;
 N-Methylation of ortho-substituted aromatic amines with methanol
 catalyzed by 2-arylbenzo[d]oxazole NHC-Ir(iii) complexes.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5072
_journal_page_last               5082
_journal_paper_doi               10.1039/c9dt00218a
_journal_volume                  48
_journal_year                    2019
_chemical_formula_sum            'C38 H42 Br0.13 Cl0.87 F6 Ir N3 O P'
_chemical_formula_weight         935.15
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-12-27 deposited with the CCDC.
2019-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.6660(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9323(4)
_cell_length_b                   20.3254(7)
_cell_length_c                   17.5400(6)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      56.98
_cell_measurement_theta_min      2.97
_cell_volume                     3733.7(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33567
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         57.030
_diffrn_reflns_theta_min         3.784
_exptl_absorpt_coefficient_mu    5.755
_exptl_absorpt_correction_T_max  0.336
_exptl_absorpt_correction_T_min  0.173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_description       block
_exptl_crystal_F_000             1866
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.771
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     524
_refine_ls_number_reflns         7625
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0301
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0231P)^2^+6.1895P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0710
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7106
_reflns_number_total             7625
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt00218a1.cif
_cod_data_source_block           ga_80412d_a
_cod_depositor_comments
'Adding full bibliography for 7049259--7049262.cif.'
_cod_database_code               7049262
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.196
_shelx_estimated_absorpt_t_max   0.392
_shelx_res_checksum              90194