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_1571920
_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_absolute_configuration unk
_chemical_formula_moiety         '0.5(C H Cl3), C46 H30 N4 O'
_chemical_formula_sum            'C46.5 H30.5 Cl1.5 N4 O'
_chemical_formula_weight         714.42
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_Hall           'P 4abw 2nw'
_space_group_name_H-M_alt        'P 41 21 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-04-25
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   14.9010(4)
_cell_length_b                   14.9010(4)
_cell_length_c                   64.976(3)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      65.08
_cell_measurement_theta_min      3.04
_cell_volume                     14427.3(9)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 0.997
_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  0.1104
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       77
_diffrn_reflns_limit_l_min       -64
_diffrn_reflns_number            70190
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.267
_diffrn_reflns_theta_min         3.043
_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    1.614
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0803 after correction.
The Ratio of minimum to maximum transmission is 0.7636.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_description       block
_exptl_crystal_F_000             5936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.427
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Flack x determined using 2785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.146(12)
_refine_ls_extinction_coef       0.00063(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     967
_refine_ls_number_reflns         12989
_refine_ls_number_restraints     1020
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          0.1378
_refine_ls_R_factor_gt           0.1089
_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^)+(0.1493P)^2^+65.4784P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2827
_refine_ls_wR_factor_ref         0.3060
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.963
_reflns_number_gt                9461
_reflns_number_total             12989
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc02416h2.cif
_cod_data_source_block           2_sq
_cod_depositor_comments
;
Adding full bibliography for 1571920--1571922.cif.

2025-05-14
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C93 H61 Cl3 N8 O2'
_cod_original_formula_weight         1428.84
_cod_original_formula_moiety         'C H Cl3, 2(C46 H30 N4 O)'
_cod_original_formula_units_Z            8
_cod_original_cell_volume        14427.3(10)
_cod_database_code               1571920
_shelx_shelxl_version_number     2018/3
_olex2_submission_special_instructions 'No special instructions were received'
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_estimated_absorpt_t_min   0.738
_shelx_estimated_absorpt_t_max   0.782
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_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. Rigid body (RIGU) restrains
 O2, N1, N2, N3, N4, C00Y, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13,
 C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25, C26, C27, C28, C29,
  C30, C31, C32, C33, C34, C35, C36, C37, C38, C39, C40, C41, C42, C43, C44,
 C45, C46
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0001
 O1, N5, N6, N7, N8, C47, C48, C49, C50, C51, C52, C53, C54, C55, C56, C57,
 C58, C59, C61, C62, C63, C64, C65, C66, C67, C68, C69, C70, C71, C72, C73, C74,
  C75, C76, C77, C78, C79, C80, C81, C82, C83, C84, C85, C86, C87, C88, C89,
 C90, C91, C92, C93
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0001
3.a Riding coordinates:
 C3(H3A,H3B,H3C)
3.b Ternary CH refined with riding coordinates:
 C94(H94)
3.c Aromatic/amide H refined with riding coordinates:
 C47(H47), C48(H48), C49(H49), C56(H56), C57(H57), C58(H58), C63(H63),
 C69(H69), C83(H83), C85(H85), C91(H91), C93(H93), C6(H6), C10(H10), C13(H13),
 C21(H21), C29(H29), C30(H30), C31(H31), C34(H34), C35(H35), C36(H36), C40(H40),
  C46(H46)
3.d Idealised Me refined as rotating group:
 C66(H66A,H66B,H66C), C67(H67A,H67B,H67C), C68(H68A,H68B,H68C), C87(H87A,H87B,
 H87C), C88(H88A,H88B,H88C), C89(H89A,H89B,H89C), C4(H4A,H4B,H4C), C12(H12A,
 H12B,H12C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              90348
_shelx_hkl_checksum              83065
_shelx_fab_checksum              55997