Rhodium(III)-Catalyzed C-H Activation of α-Iminonitriles or α-Imino Esters and Cyclization with Acrylates to 2 H-Isoindoles.
Li, Yazhou; Zhou, Jianhui; Fang, Feifei; Xu, Bin; Liu, Hong; Zhou, Yu; The Journal of organic chemistry 83 (2018) 11736–11746; doi:10.1021/acs.joc.8b01664

data_4035193
_publ_section_title
;
 Rhodium(III)-Catalyzed C-H Activation of \a-Iminonitriles or \a-Imino
 Esters and Cyclization with Acrylates to 2 H-Isoindoles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11736
_journal_page_last               11746
_journal_paper_doi               10.1021/acs.joc.8b01664
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H18 N2 O3'
_chemical_formula_sum            'C20 H18 N2 O3'
_chemical_formula_weight         334.36
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                66.523(8)
_cell_angle_beta                 88.460(9)
_cell_angle_gamma                67.367(9)
_cell_formula_units_Z            2
_cell_length_a                   9.369(3)
_cell_length_b                   10.090(3)
_cell_length_c                   10.992(4)
_cell_measurement_reflns_used    596
_cell_measurement_temperature    205
_cell_measurement_theta_max      20.25
_cell_measurement_theta_min      2.38
_cell_volume                     869.8(5)
_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      205
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0499
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6005
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_min         2.043
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0660 before and 0.0486 after correction. The Ratio of minimum to maximum transmission is 0.7957. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0950P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1880
_reflns_number_total             2984
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01664_si_002.cif
_cod_data_source_block           mo_2017818_0m
_cod_original_cell_volume        869.9(5)
_cod_database_code               4035193
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.984
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C13(H13), C14(H14), C2(H2), C4(H4), C1(H1), C3(H3)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'