Generation of N-Centered Radicals via a Photocatalytic Energy Transfer: Remote Double Functionalization of Arenes Facilitated by Singlet Oxygen.
Soni, Vineet Kumar; Hwang, Ho Seong; Moon, Yu Kyung; Park, Sung-Woo; You, Youngmin; Cho, Eun Jin; Journal of the American Chemical Society 141 (2019) 10538–10545; doi:10.1021/jacs.9b05572

data_4128005
_publ_section_title
;
 Generation of N-Centered Radicals via a Photocatalytic Energy Transfer:
 Remote Double Functionalization of Arenes Facilitated by Singlet Oxygen.
;
_journal_issue                   26
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10538
_journal_page_last               10545
_journal_paper_doi               10.1021/jacs.9b05572
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C20 H14 N2 O2'
_chemical_formula_sum            'C20 H14 N2 O2'
_chemical_formula_weight         314.33
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 93.348(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.9596(5)
_cell_length_b                   5.7704(2)
_cell_length_c                   18.2738(5)
_cell_measurement_reflns_used    1915
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.49
_cell_measurement_theta_min      2.19
_cell_volume                     1574.75(9)
_computing_cell_refinement       'Bruker APEX2'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker APEX2'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14956
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.711
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.525
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.838
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.838
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0451
_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^)+(0.1000P)^2^+0.4049P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1749
_reflns_number_total             2763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05572_si_002.cif
_cod_data_source_block
2,3-diphenyl-1,3-diazaspiro[4.5]deca-1,6,9-triene-4,8-dione
_cod_database_code               4128005
_shelx_estimated_absorpt_t_min   0.956
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2014-3
_shelx_res_checksum              99332
_shelx_hkl_checksum              53701