Rhodium(i)-catalyzed cascade C(sp<sup>2</sup>)-H bond alkylation - amidation of anilines: phosphorus as traceless directing group.
Peng, Marie; Ari, Denis; Roisnel, Thierry; Doucet, Henri; Soulé, Jean-François; Chemical science 14 (2023) 9055–9062; doi:10.1039/d3sc02992a

data_1569605
_publ_section_title
;
 Rhodium(i)-catalyzed cascade C(sp<sup>2</sup>)-H bond alkylation -
 amidation of anilines: phosphorus as traceless directing group.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              9055
_journal_page_last               9062
_journal_paper_doi               10.1039/d3sc02992a
_journal_volume                  14
_journal_year                    2023
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C10 H10 Cl N O'
_chemical_formula_sum            'C10 H10 Cl N O'
_chemical_formula_weight         195.64
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2023-03-29 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.950(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4075(13)
_cell_length_b                   6.8598(8)
_cell_length_c                   12.7321(15)
_cell_measurement_reflns_used    1745
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.4352
_cell_measurement_theta_min      2.8334
_cell_measurement_wavelength     0.710730
_cell_volume                     889.29(19)
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_orient_matrix_UB_11      0.0818586
_diffrn_orient_matrix_UB_12      -0.0669256
_diffrn_orient_matrix_UB_13      -0.0102692
_diffrn_orient_matrix_UB_21      0.0525803
_diffrn_orient_matrix_UB_22      0.1178187
_diffrn_orient_matrix_UB_23      0.0281303
_diffrn_orient_matrix_UB_31      0.0133342
_diffrn_orient_matrix_UB_32      -0.0537339
_diffrn_orient_matrix_UB_33      0.0744698
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5583
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         3.271
_diffrn_source_current           1.0
_diffrn_source_power             50.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_description       plate
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0404P)^2^+0.0687P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0930
_reflns_number_gt                1555
_reflns_number_total             2024
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d3sc02992a2.cif
_cod_data_source_block           2AD24
_cod_depositor_comments          'Adding full bibliography for 1569605.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1569605
_shelx_res_checksum              16361