Effective N-methylation of nitroarenes with methanol catalyzed by a functionalized NHC-based iridium catalyst: a green approach to N-methyl amines
González-Lainez, Miguel; Jiménez, M. Victoria; Passarelli, Vincenzo; Pérez-Torrente, Jesús J.; Catalysis Science & Technology 10 (2020) 3458–3467; doi:10.1039/D0CY00707B

data_1557983
_publ_section_title
;
 Effective N-methylation of nitroarenes with methanol catalyzed by a
 functionalized NHC-based iridium catalyst: a green approach to N-methyl
 amines
;
_journal_issue                   10
_journal_name_full               'Catalysis Science &amp; Technology'
_journal_page_first              3458
_journal_page_last               3467
_journal_paper_doi               10.1039/D0CY00707B
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C23 H33 Br Ir N3 O'
_chemical_formula_sum            'C23 H33 Br Ir N3 O'
_chemical_formula_weight         639.63
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-04-06 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.5950(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5663(3)
_cell_length_b                   11.0966(4)
_cell_length_c                   24.1272(9)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.449
_cell_measurement_theta_min      2.404
_cell_volume                     2267.70(14)
_computing_cell_refinement       'SAINT+ v. 6.45 (Bruker AXS, 2003)'
_computing_data_collection       'SMART v. 5.611 (Bruker AXS, 2000)'
_computing_data_reduction        'SAINT+ v. 6.45 (Bruker AXS, 2003)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, SHELXTLv6.12, BrukerAXS'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'Bruker SMART APEX-DUO CCD system'
_diffrn_measurement_method       '\w rotations with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            34038
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.650
_diffrn_reflns_theta_min         1.707
_exptl_absorpt_coefficient_mu    7.669
_exptl_absorpt_correction_T_max  0.3851
_exptl_absorpt_correction_T_min  0.2975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

 SADABS: Area-Detector Absorption Correction. (1996)  Bruker-AXS 

 within SAINT+ package, v. 6.45.   

;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_description       prism
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.359
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.131
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         6081
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0236
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+0.1667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0490
_refine_ls_wR_factor_ref         0.0514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5219
_reflns_number_total             6081
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cy00707b2.cif
_cod_data_source_block           cmpd_2_VPX73
_cod_depositor_comments
;Adding full bibliography for 1557983--1557984.cif.

 Adding full bibliography for 1557983--1557984.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1557983
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              13331