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_7049261
_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            'C31 H30 Cl F6 Ir N3 O P'
_chemical_formula_weight         833.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7553(6)
_cell_length_b                   16.3267(8)
_cell_length_c                   14.7234(7)
_cell_measurement_reflns_used    9886
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      58.24
_cell_measurement_theta_min      4.63
_cell_volume                     3066.2(3)
_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  0.0570
_diffrn_reflns_av_unetI/netI     0.0527
_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       -16
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20617
_diffrn_reflns_point_group_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.794
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.242
_diffrn_reflns_theta_min         4.634
_exptl_absorpt_coefficient_mu    6.835
_exptl_absorpt_correction_T_max  0.515
_exptl_absorpt_correction_T_min  0.292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_description       sheet
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.876
_refine_diff_density_min         -1.026
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
; 
 Flack x determined using 1495 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.177(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         5195
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0411P)^2^+4.3522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0889
_reflns_Friedel_coverage         0.529
_reflns_Friedel_fraction_full    0.566
_reflns_Friedel_fraction_max     0.573
_reflns_number_gt                4809
_reflns_number_total             5195
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt00218a1.cif
_cod_data_source_block           ga_80627da_d
_cod_depositor_comments
'Adding full bibliography for 7049259--7049262.cif.'
_cod_database_code               7049261
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.390
_shelx_estimated_absorpt_t_max   0.821
_shelx_res_checksum              74100