Rhodium(III)-Catalyzed Diastereoselective Ring-Opening of 7-Azabenzonorbornadienes with Aromatic Ketoximes: Synthesis of Benzophenanthridine Derivatives.
Vinayagam, Varathan; Mariappan, Arumugam; Jana, Mrinmoy; Jeganmohan, Masilamani; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02582

data_4037589
_publ_section_title
;
 Rhodium(III)-Catalyzed Diastereoselective Ring-Opening of
 7-Azabenzonorbornadienes with Aromatic Ketoximes: Synthesis of
 Benzophenanthridine Derivatives.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02582
_journal_year                    2019
_chemical_formula_sum            'C25 H30 N2 O4'
_chemical_formula_weight         845.52
_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-2014/7
_cell_angle_alpha                89.364(5)
_cell_angle_beta                 79.407(4)
_cell_angle_gamma                75.874(4)
_cell_formula_units_Z            4
_cell_length_a                   11.1405(16)
_cell_length_b                   14.6954(16)
_cell_length_c                   15.232(2)
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      2.55
_cell_volume                     2375.6(5)
_computing_cell_refinement       'Bruker SAINT'
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_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0592
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_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            28630
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        24.292
_diffrn_reflns_theta_max         24.292
_diffrn_reflns_theta_min         1.361
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       Block
_exptl_crystal_F_000             906
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0043(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         7586
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1138
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.017
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0838P)^2^+1.3707P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1617
_refine_ls_wR_factor_ref         0.1996
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4506
_reflns_number_total             7586
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02582_si_002.cif
_cod_data_source_block           mar1
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C50 H61 N4 O8'
_cod_original_formula_weight         846.02
_cod_original_formula_units_Z            2
_cod_original_cell_volume        2375.6(6)
_cod_database_code               4037589
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.988
_shelx_res_checksum              17393
_shelx_hkl_checksum              63749