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_7704061
_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         'C8 H8 I N2 O4, 0.5(H2 O), C16 H36 N'
_chemical_formula_sum            'C24 H45 I N3 O4.5'
_chemical_formula_weight         574.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-02-03
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.5298(8)
_cell_length_b                   15.7960(6)
_cell_length_c                   16.5926(6)
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    100.04
_cell_measurement_theta_max      34.1365
_cell_measurement_theta_min      2.665
_cell_volume                     5380.8(4)
_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      100.04
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0424
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            65077
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.459
_diffrn_reflns_theta_min         1.627
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    1.225
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       block
_exptl_crystal_F_000             2392
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.225
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.708
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         11334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0355
_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^)+(0.0385P)^2^+5.2657P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0932
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7704
_reflns_number_total             11334
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt00565g3.cif
_cod_data_source_block           cab013_0ma
_cod_depositor_comments
'Adding full bibliography for 7704061--7704063.cif.'
_cod_original_formula_sum        'C24 H45 I N3 O4.50'
_cod_database_code               7704061
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.867
_shelx_estimated_absorpt_t_min   0.694
_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, All O(H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5)
3.a Free rotating group:
 O5(H5A,H5B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B),
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B),
  C23(H23A,H23B)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C24(H24A,H24B,
 H24C)
;
_shelx_res_checksum              50485
_olex2_submission_special_instructions 'No special instructions were received'