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_7125998
_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         'C17 H16 Br N O2'
_chemical_formula_sum            'C17 H16 Br N O2'
_chemical_formula_weight         346.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc248w1c
_audit_creation_date             2019-12-26
_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                 107.1620(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7754(7)
_cell_length_b                   8.5582(4)
_cell_length_c                   11.6197(5)
_cell_measurement_reflns_used    4434
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.383
_cell_measurement_theta_min      2.703
_cell_volume                     1498.91(12)
_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 0.991
_diffrn_measured_fraction_theta_max 0.989
_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  0.0590
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15168
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.398
_diffrn_reflns_theta_min         2.703
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.746
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5006
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1178 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.6716. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       block
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0273P)^2^+1.1195P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0784
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2379
_reflns_number_total             3036
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08297b2.cif
_cod_data_source_block           zz
_cod_depositor_comments
'Adding full bibliography for 7125998--7126001.cif.'
_cod_database_code               7125998
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.810
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C14(H14), C13(H13), C9(H9), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'