Tandem Aza-Heck Suzuki and Carbonylation Reactions of O-Phenyl Hydroxamic Ethers: Complex Lactams via Carboamination
Watson, Donald; Gao, Run-Duo; Shular, Scott; Chemical Science  (2021) –; doi:10.1039/D1SC02075G

data_1562943
_publ_section_title
;
 Tandem&#x00A0;Aza-Heck Suzuki and Carbonylation Reactions
 of&#x00A0;O-Phenyl Hydroxamic Ethers: Complex Lactams via Carboamination
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC02075G
_journal_year                    2021
_chemical_formula_moiety         'C21 H18 N2 O2, 0.5(C H Cl3)'
_chemical_formula_sum            'C21.5 H18.5 Cl1.5 N2 O2'
_chemical_formula_weight         390.06
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-03-17 deposited with the CCDC.	2021-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                65.0970(10)
_cell_angle_beta                 73.267(2)
_cell_angle_gamma                76.047(2)
_cell_formula_units_Z            4
_cell_length_a                   11.9474(5)
_cell_length_b                   13.1954(5)
_cell_length_c                   13.9109(6)
_cell_measurement_reflns_used    9633
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      75.28
_cell_measurement_theta_min      3.58
_cell_volume                     1886.70(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            47661
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.630
_diffrn_reflns_theta_min         3.584
_exptl_absorpt_coefficient_mu    2.599
_exptl_absorpt_correction_T_max  0.7539
_exptl_absorpt_correction_T_min  0.5915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_description       plate
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.381
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     645
_refine_ls_number_reflns         7482
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.228
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0497
_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^)+(0.0702P)^2^+0.9683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1349
_refine_ls_wR_factor_ref         0.1376
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6885
_reflns_number_total             7482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc02075g2.cif
_cod_data_source_block           donw087
_cod_original_formula_sum        'C21.50 H18.50 Cl1.50 N2 O2'
_cod_database_code               1562943
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.438
_shelx_estimated_absorpt_t_max   0.860
_shelx_res_checksum              19764
_shelx_hkl_checksum              98696