Identification of key functionalization species in the Cp*Ir(III)-catalyzed-<i>ortho</i> halogenation of benzamides.
Guzmán Santiago, Alexis J; Brown, Caleb A.; Sommer, Roger D.; Ison, Elon A.; Dalton transactions (Cambridge, England : 2003) 49 (2020) 16166–16174; doi:10.1039/d0dt00565g

data_7704062
_publ_section_title
;
 Identification of key functionalization species in the
 Cp*Ir(III)-catalyzed-<i>ortho</i> halogenation of benzamides.
;
_journal_issue                   45
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16166
_journal_page_last               16174
_journal_paper_doi               10.1039/d0dt00565g
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C6 H7 I N O4, C16 H36 N'
_chemical_formula_sum            'C22 H43 I N2 O4'
_chemical_formula_weight         526.48
_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
_audit_creation_date             2020-01-22
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-02-06 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_cell_angle_alpha                74.4690(10)
_cell_angle_beta                 80.475(2)
_cell_angle_gamma                88.799(2)
_cell_formula_units_Z            4
_cell_length_a                   7.9117(4)
_cell_length_b                   15.8043(7)
_cell_length_c                   21.3583(10)
_cell_measurement_reflns_used    9773
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      32.1875
_cell_measurement_theta_min      2.676
_cell_volume                     2536.9(2)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            231113
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.490
_diffrn_reflns_theta_min         1.003
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.290
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_description       rod
_exptl_crystal_F_000             1096
_refine_diff_density_max         5.515
_refine_diff_density_min         -1.061
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     533
_refine_ls_number_reflns         24763
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.140
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0531P)^2^+2.0293P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1123
_reflns_Friedel_coverage         0.000
_reflns_number_gt                19506
_reflns_number_total             24763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt00565g3.cif
_cod_data_source_block           cab015_0m
_cod_depositor_comments
'Adding full bibliography for 7704061--7704063.cif.'
_cod_database_code               7704062
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C35-C36 \\sim C34-C35
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C24(H24A,H24B), C25(H25A,H25B), C7(H7A,H7B), C8(H8A,
 H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B),
 C21(H21A,H21B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B),
  C34(H34A,H34B), C35(H35A,H35B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,
 H39B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B)
3.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C28(H28A,H28B,H28C), C10(H10A,H10B,H10C), C14(H14A,H14B,
 H14C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C32(H32A,H32B,H32C), C36(H36A,
 H36B,H36C), C40(H40A,H40B,H40C), C44(H44A,H44B,H44C)
;
_shelx_res_checksum              16990
_olex2_submission_special_instructions 'No special instructions were received'