Oxidation of Annelated Diarylamines: Analysis of Reaction Pathways to Nitroxide Diradical and Spirocyclic Products
Andrzej Rajca; Kouichi Shiraishi; Przemysław J. Boratyński; Maren Pink; Makoto Miyasaka; Suchada Rajca; Journal of Organic Chemistry 76 (2011) 8447–8457; doi:10.1021/jo2017923

data_4026672
_publ_section_title
;
 Oxidation of Annelated Diarylamines: Analysis of Reaction Pathways to
 Nitroxide Diradical and Spirocyclic Products
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8447
_journal_page_last               8457
_journal_paper_doi               10.1021/jo2017923
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C32 H38 N2 O2, 1.5 (C H2 Cl2)'
_chemical_formula_sum            'C33.5 H41 Cl3 N2 O2'
_chemical_formula_weight         610.03
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.722(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.920(2)
_cell_length_b                   13.8734(17)
_cell_length_c                   19.672(2)
_cell_measurement_reflns_used    6358
_cell_measurement_temperature    95(2)
_cell_measurement_theta_max      18.9
_cell_measurement_theta_min      2.2
_cell_volume                     6273.3(11)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2003), XTEL (loc. libr.)'
_computing_publication_material  'SHELXTL (Bruker, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      95(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 44.52
_diffrn_detector_type            'Bruker SMART 6000'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      '0.5 degree frames measured for 1 seconds each'
_diffrn_measurement_device       'three-circle goniometer with fixed chi'
_diffrn_measurement_device_type  'Bruker Platform goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'diamond 1 1 1'
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.49595
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            116495
_diffrn_reflns_theta_full        19.03
_diffrn_reflns_theta_max         19.03
_diffrn_reflns_theta_min         1.20
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.9974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing; 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_description       block
_exptl_crystal_F_000             2584
_exptl_crystal_size_max          0.015
_exptl_crystal_size_mid          0.011
_exptl_crystal_size_min          0.005
_refine_diff_density_max         1.378
_refine_diff_density_min         -1.123
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     776
_refine_ls_number_reflns         14907
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0765
_refine_ls_R_factor_gt           0.0546
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0699P)^2^+6.4808P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1470
_reflns_number_gt                11401
_reflns_number_total             14907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2017923_si_002.cif
_cod_data_source_block           05503
_cod_original_cell_volume        6273.3(12)
_cod_original_formula_sum        'C33.50 H41 Cl3 N2 O2'
_cod_database_code               4026672