Multi-heteroatom doped nanographenes: enhancing photosensitization capacity by forming an electron donor-acceptor architecture.
Li, Ranran; Ma, Bin; Li, Meng; Wang, Dan; Liu, Peng; An, Peng; Chemical science 15 (2024) 11408–11417; doi:10.1039/d4sc02416h

data_1571922
_publ_section_title
;
 Multi-heteroatom doped nanographenes: enhancing photosensitization
 capacity by forming an electron donor-acceptor architecture.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              11408
_journal_page_last               11417
_journal_paper_doi               10.1039/d4sc02416h
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         '2(C46 H32 N4 Se), C H2 Cl2'
_chemical_formula_sum            'C93 H66 Cl2 N8 Se2'
_chemical_formula_weight         1524.35
_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     direct
_audit_creation_date             2023-05-25
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2024-03-30 deposited with the CCDC.	2024-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                101.977(3)
_cell_angle_beta                 92.500(3)
_cell_angle_gamma                105.115(3)
_cell_formula_units_Z            2
_cell_length_a                   13.9675(10)
_cell_length_b                   15.5987(11)
_cell_length_c                   17.3739(13)
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      68.47
_cell_measurement_theta_min      2.61
_cell_volume                     3555.6(5)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            53367
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.465
_diffrn_reflns_theta_min         2.614
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.434
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1370 before and 0.0652 after correction.
The Ratio of minimum to maximum transmission is 0.7157.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_description       plate
_exptl_crystal_F_000             1564
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.892
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     989
_refine_ls_number_reflns         12993
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0390
_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^)+(0.0335P)^2^+4.6813P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12170
_reflns_number_total             12993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02416h2.cif
_cod_data_source_block           1_sq
_cod_depositor_comments
'Adding full bibliography for 1571920--1571922.cif.'
_cod_original_cell_volume        3555.6(4)
_cod_database_code               1571922
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C23, C91, C45, C39
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.001
 C23A, C45A, C91A, C39
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.001
3. Others
 Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=Sof(C91A)=Sof(H91D)=Sof(H91E)=
 Sof(H91F)=Sof(C45A)=Sof(H45D)=Sof(H45E)=Sof(H45F)=1-FVAR(1)
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=
 Sof(C91)=Sof(H91A)=Sof(H91B)=Sof(H91C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C87(H87A,H87B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C13(H13), C19(H19), C20(H20), C25(H25), C27(H27), C31(H31), C47(H47),
 C54(H54), C59(H59), C65(H65), C76(H76), C81(H81), C86(H86), C2(H2), C15(H15),
 C17(H17), C29(H29), C33(H33), C34(H34), C41(H41), C57(H57), C63(H63), C66(H66),
  C67(H67), C69(H69), C71(H71), C73(H73)
4.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C37(H37A,H37B,H37C), C43(H43A,H43B,H43C), C79(H79A,H79B,
 H79C), C85(H85A,H85B,H85C), C89(H89A,H89B,H89C), C11(H11A,H11B,H11C), C21(H21A,
 H21B,H21C), C23(H23A,H23B,H23C), C45(H45A,H45B,H45C), C83(H83A,H83B,H83C),
 C91(H91A,H91B,H91C), C23A(H23D,H23E,H23F), C91A(H91D,H91E,H91F), C45A(H45D,
 H45E,H45F)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_t_min   0.593
_shelx_estimated_absorpt_t_max   0.793
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_shelx_res_checksum              62695
_shelx_hkl_checksum              37815
_shelx_fab_checksum              1448