Deprotonation of Benzoxazolium Salt: Trapping of a Radical-Cation Intermediate
Klementyeva, S.V.; Abramov, P.A.; Somov, N.V.; Dudkina, Yu.B.; Budnikova, Yu.H.; sky, A.I.; Organic Letters 21 (2019) 946–950; doi:10.1021/acs.orglett.8b03928

data_1564831
_publ_section_title
;
 Deprotonation of Benzoxazolium Salt: Trapping of a Radical-Cation
 Intermediate
;
_journal_issue                   4
_journal_name_full
;
 Organic Letters
;
_journal_page_first              946
_journal_page_last               950
_journal_paper_doi               10.1021/acs.orglett.8b03928
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_sum            'C54 H74 N2 O2'
_chemical_formula_weight         783.15
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-06-27T16:22:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7071(7)
_cell_length_b                   19.5593(8)
_cell_length_c                   22.8987(11)
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      1.78
_cell_volume                     4795.5(4)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1428
_diffrn_reflns_av_unetI/netI     0.1877
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            43317
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         1.779
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9951
_exptl_absorpt_correction_T_min  0.9841
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_description       fragment
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.235
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1293 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.803
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         11900
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.803
_refine_ls_R_factor_all          0.1822
_refine_ls_R_factor_gt           0.0711
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0380P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1332
_reflns_Friedel_coverage         0.813
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_number_gt                4918
_reflns_number_total             11900
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            tmpr3vwy_x8
_cod_data_source_block           39p212121
_cod_database_code               1564831