Ir(iii)-Catalyzed direct C-H functionalization of N-phenylacetamide with α-diazo quinones: a novel strategy for producing 2-hydroxy-2'-amino-1,2'-biaryl scaffolds.
Li, Xingjun; Wang, Jiang; Xie, Xiong; Dai, Wenhao; Han, Xu; Chen, Kaixian; Liu, Hong; Chemical communications (Cambridge, England) 56 (2020) 3441–3444; doi:10.1039/c9cc08297b

data_7125999
_publ_section_title
;
 Ir(iii)-Catalyzed direct C-H functionalization of N-phenylacetamide with
 \a-diazo quinones: a novel strategy for producing
 2-hydroxy-2'-amino-1,2'-biaryl scaffolds.
;
_journal_issue                   23
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3441
_journal_page_last               3444
_journal_paper_doi               10.1039/c9cc08297b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C20 H14 Br N O3'
_chemical_formula_sum            'C20 H14 Br N O3'
_chemical_formula_weight         396.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc248w2d
_audit_creation_date             2019-12-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-30 deposited with the CCDC.	2020-02-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2743(5)
_cell_length_b                   15.4368(16)
_cell_length_c                   24.939(3)
_cell_measurement_reflns_used    2045
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.512
_cell_measurement_theta_min      2.370
_cell_volume                     1645.5(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170.0
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.1007
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            7712
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.506
_diffrn_reflns_theta_min         2.639
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.517
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4853
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1429 before and 0.0772 after correction. The Ratio of minimum to maximum transmission is 0.6511. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.100
_refine_ls_abs_structure_details
;
 Flack x determined using 668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.194(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0513
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.2479P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.650
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.952
_reflns_number_gt                2289
_reflns_number_total             3328
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08297b2.cif
_cod_data_source_block           220191293lxj_0m
_cod_depositor_comments
'Adding full bibliography for 7125998--7126001.cif.'
_cod_database_code               7125999
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.704
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1A), C17(H17), C19(H19), C11(H11), C20(H20), C12(H12), C5(H5), C4(H4),
 C3(H3), C2(H2)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'