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_1554349
_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         '0.06(C88 H90 N2 O8)'
_chemical_formula_sum            'C5.5 H5.62 N0.12 O0.5'
_chemical_formula_weight         81.48
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d :2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-04-03
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2015.06.08 svn.r3188 for OlexSys, GUI svn.r5047)
;
_audit_update_record
;
2018-04-04 deposited with the CCDC.
2018-05-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            128
_cell_length_a                   24.1341(14)
_cell_length_b                   25.4123(13)
_cell_length_c                   26.6380(17)
_cell_measurement_reflns_used    3608
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.028
_cell_measurement_theta_min      2.277
_cell_volume                     16337.2(16)
_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    'SIR2004 (Burla et al., 2007)'
_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  0.0327
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.028
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_min         2.277
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76001
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.060
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             5568
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.080
_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     229
_refine_ls_number_reflns         3608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0766
_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^)+(0.1554P)^2^+23.8375P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2293
_refine_ls_wR_factor_ref         0.2440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2685
_reflns_number_total             3608
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00445e2.cif
_cod_data_source_block           fddd
_cod_original_sg_symbol_H-M      'F d d d'
_cod_original_formula_sum        'C5.50 H5.62 N0.12 O0.50'
_cod_database_code               1554349
_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:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C16(H16), C17(H17), C20(H20), C19(H19), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C4(H4A,H4B,
 H4C), C3(H3A,H3B,H3C)
;
_shelx_res_checksum              5379
_shelx_hkl_checksum              34648
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'