Reversal of polarity by catalytic SET oxidation: synthesis of azabicyclo[<i>m</i>.<i>n</i>.0]alkanes <i>via</i> chemoselective reduction of amidines.
Devarahosahalli Veeranna, Kirana; Kanti Das, Kanak; Baskaran, Sundarababu; Organic & biomolecular chemistry 19 (2021) 4054–4059; doi:10.1039/d1ob00416f

data_7158020
_publ_section_title
;
 Reversal of polarity by catalytic SET oxidation: synthesis of
 azabicyclo[<i>m</i>.<i>n</i>.0]alkanes <i>via</i> chemoselective
 reduction of amidines.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4054
_journal_page_last               4059
_journal_paper_doi               10.1039/d1ob00416f
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C24 H26 N2 O4 S'
_chemical_formula_sum            'C24 H26 N2 O4 S'
_chemical_formula_weight         438.52
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-01-10 deposited with the CCDC.	2021-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.4001(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.7942(7)
_cell_length_b                   11.5133(3)
_cell_length_c                   21.0097(7)
_cell_measurement_reflns_used    5943
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.45
_cell_measurement_theta_min      2.21
_cell_volume                     4465.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0386
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            24678
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.140
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_description       Block
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     563
_refine_ls_number_reflns         7862
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0581P)^2^+5.1089P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1677
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5007
_reflns_number_total             7862
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ob00416f2.cif
_cod_data_source_block           901
_cod_depositor_comments
;
Adding full bibliography for 7158020--7158024.cif.

2024-12-16
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_moiety     'C48 H52 N4 O8 S2'
_cod_original_formula_sum        'C48 H52 N4 O8 S2'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     877.05
_cod_database_code               7158020
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.979
_shelx_res_checksum              43452
_shelx_hkl_checksum              13974