Photoexcited perylene diimide radical anions for the reduction of aryl halides: a bay-substituent effect
Gong, Hai-Xian; Cao, Zhu; Li, Meng-Hua; Liao, Sai-Hu; Lin, Mei-Jin; Organic Chemistry Frontiers 5 (2018) 2296–; doi:10.1039/C8QO00445E

data_1554350
_publ_section_title
;
 Photoexcited perylene diimide radical anions for the reduction of aryl
 halides: a bay-substituent effect
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2296
_journal_paper_doi               10.1039/C8QO00445E
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C34 H33 N O3'
_chemical_formula_sum            'C34 H33 N O3'
_chemical_formula_weight         503.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-17
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-04 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                87.132(5)
_cell_angle_beta                 84.213(5)
_cell_angle_gamma                68.822(5)
_cell_formula_units_Z            2
_cell_length_a                   9.4355(5)
_cell_length_b                   10.2231(6)
_cell_length_c                   17.9161(11)
_cell_measurement_reflns_used    3880
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.8070
_cell_measurement_theta_min      2.4550
_cell_volume                     1603.09(17)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            19426
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.285
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.043
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5664
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0845
_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^)+(0.0857P)^2^+2.4953P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2197
_refine_ls_wR_factor_ref         0.2349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3804
_reflns_number_total             5664
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00445e2.cif
_cod_data_source_block           p-1
_cod_database_code               1554350
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C33(H33), C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C15(H15), C9(H9), C14(H14), C18(H18), C17(H17), C29(H29),
 C27(H27), C28(H28)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C32(H32A,H32B,H32C), C20(H20A,H20B,H20C), C23(H23A,H23B,
 H23C), C34(H34A,H34B,H34C), C25(H25A,H25B,H25C), C19(H19A,H19B,H19C)
;
_olex2_submission_special_instructions 'No special instructions were received'