Radical Cations of Phenoxazine and Dihydrophenazine Photoredox Catalysts and Their Role as Deactivators in Organocatalyzed Atom Transfer Radical Polymerization
Corbin, Daniel A.; McCarthy, Blaine G.; van de Lindt, Zach; Miyake, Garret M.; Macromolecules 54 (2021) 4726–4738; doi:10.1021/acs.macromol.1c00640

data_1562360
_publ_section_title
;
 Radical Cations of Phenoxazine and Dihydrophenazine Photoredox Catalysts
 and Their Role as Deactivators in Organocatalyzed Atom Transfer Radical
 Polymerization
;
_journal_issue                   10
_journal_name_full               Macromolecules
_journal_page_first              4726
_journal_page_last               4738
_journal_paper_doi               10.1021/acs.macromol.1c00640
_journal_volume                  54
_journal_year                    2021
_chemical_formula_moiety         'Cl6 Sb, C0.5 H Cl, C46 H31 N O'
_chemical_formula_sum            'C46.5 H32 Cl7 N O Sb'
_chemical_formula_weight         990.63
_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_date             2020-10-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.686(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6418(5)
_cell_length_b                   18.8802(7)
_cell_length_c                   18.9143(7)
_cell_measurement_reflns_used    546
_cell_measurement_temperature    99.97
_cell_measurement_theta_max      17.70
_cell_measurement_theta_min      2.42
_cell_volume                     4155.6(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0919
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            151177
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.029
_diffrn_reflns_theta_max         25.029
_diffrn_reflns_theta_min         1.524
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.152
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6932
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0649 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9286.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_description       rod
_exptl_crystal_F_000             1984
_exptl_crystal_size_max          0.094
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.056
_refine_diff_density_max         1.103
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         7336
_refine_ls_number_restraints     67
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0990
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0298P)^2^+18.5188P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5106
_reflns_number_total             7336
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ma1c00640_si_003.cif
_cod_data_source_block           gm106_0m_20200909_a
_cod_depositor_comments
'Adding full bibliography for 1562359--1562360.cif.'
_cod_original_formula_sum        'C46.50 H32 Cl7 N O Sb'
_cod_database_code               1562360
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C8-C10 = C2-C10 = C3-C2 = C4-C3 = C4-C1 = C8-C1
 1.4 with sigma of 0.02
 C7-C5 = C6-C5 = C9-C6 = C9-C2 = C3-C2 = C4-C3 = C7-C3 = C2-C10 = C8-C10 = C8-
 C1 = C4-C1
 1.4 with sigma of 0.02
 C6-C9 = C4-C1 = C8-C10
 1.4 with sigma of 0.02
 C3-C2 = C10-C8 = C4-C1
 1.4 with sigma of 0.02
 C8-C1 = C4-C1 = C4-C3 = C3-C2 = C2-C10 = C8-C10 = C8A-C3A = C3A-C2A = C2A-
 C10A = C8A-C1A = C4A-C1A = C4A-C10A = C7-C3 = C7-C5 = C5A-C2A = C7A-C3A = C9A-
 C7A = C9A-C6A = C6A-C5A = C6-C5 = C9-C6 = C9-C2
 1.4 with sigma of 0.1
 C6A-C5A = C9A-C6A = C9A-C7A = C7A-C3A = C3A-C2A = C5A-C2A = C2A-C10A = C8A-
 C3A = C8A-C1A = C4A-C1A = C4A-C10A = C7-C3 = C3-C2 = C9-C2 = C6-C5 = C9-C6 =
 C7-C5 = C4-C3 = C2-C10 = C8-C10 = C8-C1 = C4-C1
 1.4 with sigma of 0.2
3. Others
 Sof(C4A)=Sof(H4A)=Sof(C8A)=Sof(H8A)=Sof(C1A)=Sof(C10A)=Sof(H10A)=Sof(C3A)=
 Sof(C2A)=Sof(C7A)=Sof(H7A)=Sof(C9A)=Sof(H9A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6A)=1-FVAR(1)
 Sof(C1)=Sof(C4)=Sof(H4)=Sof(C8)=Sof(H8)=Sof(C2)=Sof(C3)=Sof(C10)=Sof(H10)=
 Sof(C9)=Sof(H9)=Sof(C6)=Sof(H6)=Sof(C5)=Sof(H5)=Sof(C7)=Sof(H7)=FVAR(1)
 Sof(C01H)=Sof(H01H)=Sof(C01J)=Sof(H01J)=1-FVAR(2)
 Sof(C01G)=Sof(H01G)=Sof(C01I)=Sof(H01I)=FVAR(2)
 Fixed Sof: C11(0.5) H11A(0.5) H11B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00F(H00F), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00P(H00P), C00S(H00S), C00T(H00T), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Z(H00Z), C010(H010), C012(H012), C015(H015), C017(H017),
 C018(H018), C019(H019), C01B(H01B), C01C(H01C), C01G(H01G), C01I(H01I), C4(H4),
  C8(H8), C10(H10), C9(H9), C6(H6), C5(H5), C7(H7), C4A(H4A), C8A(H8A),
 C10A(H10A), C7A(H7A), C9A(H9A), C5A(H5A), C6A(H6A), C01H(H01H), C01J(H01J)
;
_shelx_res_checksum              76616
_shelx_hkl_checksum              12090
_olex2_submission_special_instructions 'No special instructions were received'