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_7049260
_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            'C27.5 H34 Cl F6 Ir N O3 P'
_chemical_formula_weight         799.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.508(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.1859(9)
_cell_length_b                   12.0306(5)
_cell_length_c                   29.5949(16)
_cell_measurement_reflns_used    4069
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.28
_cell_measurement_theta_min      3.45
_cell_volume                     6090.7(5)
_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  0.0559
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            48562
_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         59.419
_diffrn_reflns_theta_min         2.488
_exptl_absorpt_coefficient_mu    6.878
_exptl_absorpt_correction_T_max  0.581
_exptl_absorpt_correction_T_min  0.342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_description       block
_exptl_crystal_F_000             3144
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.070
_refine_diff_density_max         9.651
_refine_diff_density_min         -4.097
_refine_diff_density_rms         0.403
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     746
_refine_ls_number_reflns         13412
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0834
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1734P)^2^+9.4139P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2137
_refine_ls_wR_factor_ref         0.2208
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12250
_reflns_number_total             13412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt00218a1.cif
_cod_data_source_block           ga_70402c_a
_cod_depositor_comments
'Adding full bibliography for 7049259--7049262.cif.'
_cod_original_formula_sum        'C27.50 H34 Cl F6 Ir N O3 P'
_cod_database_code               7049260
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.268
_shelx_estimated_absorpt_t_max   0.645
_shelx_res_checksum              68819