Perylene with peripherally fused pyrrole and pyridine: columnar packing, anti-Kasha dual emission and reactive oxygen species generation
Cao, Jing; Zhang, Wenhao; Ding, Yeda; Zhang, Xuejin; Zhang, Yuanyuan; Qiao, Dan; Biao, Shumin; Dong, Xuefei; Song, Jiayi; Dai, Gaole; Zhao, Ruiguo; Wang, Qing; New Journal of Chemistry 48 (2024) 9014–9019; doi:10.1039/D4NJ01177E

data_7063149
_publ_section_title
;
 Perylene with peripherally fused pyrrole and pyridine: columnar packing,
 anti-Kasha dual emission and reactive oxygen species generation
;
_journal_issue                   20
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              9014
_journal_page_last               9019
_journal_paper_doi               10.1039/D4NJ01177E
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C39 H20 F10 N2'
_chemical_formula_sum            'C39 H20 F10 N2'
_chemical_formula_weight         706.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-05-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.948(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   10.3159(5)
_cell_length_b                   30.2698(11)
_cell_length_c                   15.1352(6)
_cell_measurement_reflns_used    5975
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      54.408
_cell_measurement_theta_min      2.540
_cell_volume                     4586.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_diffrn_ambient_temperature      193.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28223
_diffrn_reflns_point_group_measured_fraction_full 0.768
_diffrn_reflns_point_group_measured_fraction_max 0.751
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.998
_diffrn_reflns_theta_min         2.540
_diffrn_source_current           2.86
_diffrn_source_power             0.1993706
_diffrn_source_voltage           69.71
_exptl_absorpt_coefficient_mu    0.737
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS; Bruker, 2018'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_description       block
_exptl_crystal_F_000             2148
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 3051 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1381
_refine_ls_number_reflns         13636
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0486
_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^)+(0.07P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1133
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.490
_reflns_Friedel_fraction_full    0.534
_reflns_Friedel_fraction_max     0.504
_reflns_number_gt                10466
_reflns_number_total             13636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4nj01177e2.cif
_cod_data_source_block           fff
_cod_depositor_comments          'Adding full bibliography for 7063149.cif.'
_cod_database_code               7063149
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.879
_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.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,
 H38B), C73(H73A,H73B), C74(H74A,H74B), C75(H75A,H75B), C76(H76A,H76B),
 C77(H77A,H77B), C112(H11A,H11B), C113(H11C,H11D), C114(H11E,H11F), C115(H11G,
 H11H), C116(H11I,H11J)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C12(H12), C15(H15), C18(H18), C19(H19), C21(H21), C47(H47),
 C48(H48), C51(H51), C54(H54), C57(H57), C58(H58), C60(H60), C86(H86), C87(H87),
  C90(H90), C93(H93), C96(H96), C97(H97), C99(H99)
2.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C78(H78A,H78B,H78C), C117(H11K,H11L,H11M)
;
_olex2_submission_special_instructions 'No special instructions were received'