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_1557984
_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         'C17 H21 Br Ir N3 O3'
_chemical_formula_sum            'C17 H21 Br Ir N3 O3'
_chemical_formula_weight         587.48
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-07-23 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                99.1570(10)
_cell_angle_beta                 110.946(2)
_cell_angle_gamma                114.3940(10)
_cell_formula_units_Z            2
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_cell_length_b                   11.1211(11)
_cell_length_c                   11.8920(19)
_cell_measurement_reflns_used    7571
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.267
_cell_measurement_theta_min      2.335
_cell_volume                     968.3(2)
_computing_cell_refinement       'SAINT+ in APEX2 (Bruker AXS,2008)'
_computing_data_collection       'SMART in APEX2 (Bruker AXS,2008)'
_computing_data_reduction        'SAINT+ in APEX2 (Bruker AXS,2008)'
_computing_molecular_graphics    'XP program, SHELXTL v6.12, Bruker2000'
_computing_publication_material  'XCIF program, PLATON(Spek, 1998)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX DUO system'
_diffrn_measurement_method       '\w and \f 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  0.0210
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11641
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
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_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         1.966
_exptl_absorpt_coefficient_mu    8.978
_exptl_absorpt_correction_T_max  0.1695
_exptl_absorpt_correction_T_min  0.1208
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 Multi-scan correction included in APEX2 package (Bruker AXS, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         2.507
_refine_diff_density_min         -2.000
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3938
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0311P)^2^+5.1495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0740
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3700
_reflns_number_total             3938
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cy00707b2.cif
_cod_data_source_block           cmpd_4_VPX142
_cod_depositor_comments
;Adding full bibliography for 1557983--1557984.cif.

 Adding full bibliography for 1557983--1557984.cif.
;
_cod_database_code               1557984
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              46055