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_7704063
_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         'C25 H39 Ir N O2 S, C F3 O3 S'
_chemical_formula_sum            'C26 H39 F3 Ir N O5 S2'
_chemical_formula_weight         758.90
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_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                 100.901(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.1476(14)
_cell_length_b                   8.1712(5)
_cell_length_c                   17.1899(11)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      34.0175
_cell_measurement_theta_min      2.4135
_cell_volume                     2916.8(3)
_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      296.15
_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  0.0206
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            53681
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.604
_diffrn_reflns_theta_min         1.961
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.776
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_description       needles
_exptl_crystal_F_000             1512
_refine_diff_density_max         4.710
_refine_diff_density_min         -1.331
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details
;
 Flack x determined using 8211 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4058(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     771
_refine_ls_number_reflns         17713
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0272
_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^)+(0.0138P)^2^+13.0113P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0601
_reflns_Friedel_coverage         0.977
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                17355
_reflns_number_total             17713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0dt00565g3.cif
_cod_data_source_block           cab011_0ma
_cod_depositor_comments
'Adding full bibliography for 7704061--7704063.cif.'
_cod_original_sg_symbol_H-M      'P c'
_cod_database_code               7704063
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F4-C53 \\sim F6-C53 \\sim F5-C53
 with sigma of 0.02
3. Same fragment restrains
{F4A, F6A, F5A, O8A, O9A, O10A, C53A} sigma for 1-2: 0.02, 1-3: 0.04
as in
{F4, F6, F5, O8, O9, O10, C53}
4. Others
 Sof(F4A)=Sof(F6A)=Sof(F5A)=Sof(O8A)=Sof(O9A)=Sof(O10A)=Sof(C53A)=1-FVAR(1)
 Sof(F4)=Sof(F6)=Sof(F5)=Sof(O8)=Sof(O9)=Sof(O10)=Sof(C53)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12), C34(H34), C37(H37)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C28(H28), C29(H29), C30(H30), C31(H31)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,
 H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C),
 C35(H35A,H35B,H35C), C36(H36A,H36B,H36C), C38(H38A,H38B,H38C), C39(H39A,H39B,
 H39C), C45(H45A,H45B,H45C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C)
;
_shelx_res_checksum              18448
_olex2_submission_special_instructions 'No special instructions were received'