Rhodium(III)-Catalyzed Redox-Neutral 1,1-Cyclization of N-Methoxy Benzamides with Maleimides via C-H/N-H/N-O Activation: Detailed Mechanistic Investigation.
Ramesh, Balu; Tamizmani, Masilamani; Jeganmohan, Masilamani; The Journal of organic chemistry 84 (2019) 4058–4071; doi:10.1021/acs.joc.9b00051

data_4034224
_publ_section_title
;
 Rhodium(III)-Catalyzed Redox-Neutral 1,1-Cyclization of N-Methoxy
 Benzamides with Maleimides via C-H/N-H/N-O Activation: Detailed
 Mechanistic Investigation.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4058
_journal_page_last               4071
_journal_paper_doi               10.1021/acs.joc.9b00051
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C19 H16 N2 O4'
_chemical_formula_sum            'C19 H16 N2 O4'
_chemical_formula_weight         336.35
_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'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.5267(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3441(7)
_cell_length_b                   5.5569(3)
_cell_length_c                   18.2798(8)
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.43
_cell_measurement_theta_min      2.34
_cell_volume                     1680.01(14)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.9997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10164
_diffrn_reflns_theta_full        24.9983
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.29
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0642 before and 0.0449 after correction.
The Ratio of minimum to maximum transmission is 0.9141.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3297
_exptl_crystal_description       Block
_exptl_crystal_F_000             704.3844
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.2376
_refine_diff_density_min         -0.2020
_refine_diff_density_rms         0.0518
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             8.8939
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0570
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0570
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0398
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.2114P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1022
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -20
_reflns_limit_k_max              6
_reflns_limit_k_min              0
_reflns_limit_l_max              21
_reflns_limit_l_min              0
_reflns_number_gt                2015
_reflns_number_total             2971
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b00051_si_002.cif
_cod_data_source_block           449
_cod_database_code               4034224
_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:
 C9(H9a,H9b), C12(H12a,H12b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C19(H19a,H19b,H19c)
;
_olex2_submission_special_instructions 'No special instructions were received'