Regioselective and Stereoselective Reductive Aziridinium Ring Cleavage Leading to Azabicyclodecane Architecture: Enantioselective Synthesis of (+)-Subincanadine F.
Kalshetti, Manojkumar G.; Argade, Narshinha P.; The Journal of organic chemistry 83 (2018) 12164–12170; doi:10.1021/acs.joc.8b02113

data_4035191
_publ_section_title
;
 Regioselective and Stereoselective Reductive Aziridinium Ring Cleavage
 Leading to Azabicyclodecane Architecture: Enantioselective Synthesis of
 (+)-Subincanadine F.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12164
_journal_page_last               12170
_journal_paper_doi               10.1021/acs.joc.8b02113
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl, C20 H27 N2 O2, O'
_chemical_formula_sum            'C20 H27 Cl N2 O3'
_chemical_formula_weight         378.88
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-07-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1049(13)
_cell_length_b                   13.229(3)
_cell_length_c                   18.910(5)
_cell_measurement_reflns_used    7457
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.32
_cell_measurement_theta_min      5.93
_cell_volume                     2027.5(8)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10405
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.320
_diffrn_reflns_theta_min         4.078
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.837
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.4911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1564 before and 0.0899 after correction. The Ratio of minimum to maximum transmission is 0.6515. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.641
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.101(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3866
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0758
_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^)+(0.1340P)^2^+1.0612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2004
_refine_ls_wR_factor_ref         0.2104
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                3449
_reflns_number_total             3866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02113_si_002.cif
_cod_data_source_block           kap_04_0m-auto
_cod_original_cell_volume        2027.6(8)
_cod_database_code               4035191
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N1(H1), C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C9(H9), C10(H10), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_olex2_submission_special_instructions 'No special instructions were received'