Ir(III)/MPAA-Catalyzed Mild and Selective C-H Amidation of N-Sulfonyl Ketimines: Access To Benzosultam-Fused Quinazolines/Quinazolinones.
Mishra, Aniket; Mukherjee, Upasana; Vats, Tripta Kumari; Deb, Indubhusan; The Journal of organic chemistry 83 (2018) 3756–3767; doi:10.1021/acs.joc.8b00125

data_4035454
_publ_section_title
;
 Ir(III)/MPAA-Catalyzed Mild and Selective C-H Amidation of N-Sulfonyl
 Ketimines: Access To Benzosultam-Fused Quinazolines/Quinazolinones.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3756
_journal_page_last               3767
_journal_paper_doi               10.1021/acs.joc.8b00125
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H14 N2 O3 S'
_chemical_formula_sum            'C20 H14 N2 O3 S'
_chemical_formula_weight         362.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 102.365(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.368(4)
_cell_length_b                   14.888(4)
_cell_length_c                   7.803(2)
_cell_measurement_reflns_used    6773
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.71
_cell_volume                     1743.9(8)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11331
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.005
_diffrn_reflns_theta_min         2.714
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0940 before and 0.0445 after correction. The Ratio of minimum to maximum transmission is 0.8946. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_recrystallization_method 'DCM:Hexane Solvent Mixture'
_exptl_crystal_size_max          0.89
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1561 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0517P)^2^+0.1692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.949
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                3432
_reflns_number_total             3668
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00125_si_005.cif
_cod_data_source_block           ibd_am07_76_0m_a
_cod_database_code               4035454
_shelxl_version_number           2014/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C11(H11), C4(H4), C5(H5), C10(H10), C2(H2A), C12(H12), C9(H9), C3(H3),
  C17(H17), C16(H16), C20(H20), C18(H18), C19(H19)
;
_shelx_res_checksum              96321
_shelx_hkl_checksum              44510
_olex2_submission_special_instructions 'No special instructions were received'