Dual-channel deep-NIR-emissive N-embedded PAHs with hybridized local and charge-transfer excited-state.
Li, Zuhao; Zhou, Zhiruo; Yang, Kun; Yao, Yifan; Zhai, Yaxin; Wang, Dong; Zeng, Zebing; Chemical science 16 (2025) 16792–16800; doi:10.1039/d5sc01897h

data_1575951
_publ_section_title
;
 Dual-channel deep-NIR-emissive N-embedded PAHs with hybridized local and
 charge-transfer excited-state.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              16792
_journal_page_last               16800
_journal_paper_doi               10.1039/d5sc01897h
_journal_volume                  16
_journal_year                    2025
_chemical_formula_moiety         'C52 H32 N2 O2, 1.5[CCl4]'
_chemical_formula_sum            'C53.5 H32 Cl6 N2 O2'
_chemical_formula_weight         947.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-01-03
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-01-04 deposited with the CCDC.	2025-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.747(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.0331(11)
_cell_length_b                   21.6500(7)
_cell_length_c                   13.5723(5)
_cell_measurement_reflns_used    3272
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      59.185
_cell_measurement_theta_min      2.590
_cell_volume                     10026.3(6)
_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_temperature      150.00
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0816
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            35576
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        66.752
_diffrn_reflns_theta_max         66.752
_diffrn_reflns_theta_min         4.533
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    3.449
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.6133
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1146 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.8147.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             3880
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.196
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         8547
_refine_ls_number_restraints     173
_refine_ls_restrained_S_all      1.189
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.1119
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3361
_refine_ls_wR_factor_ref         0.3848
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4333
_reflns_number_total             8547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc01897h2.cif
_cod_data_source_block           cu_2024080502_1_0m
_cod_original_cell_volume        10026.2(6)
_cod_original_formula_sum        'C53.50 H32 Cl6 N2 O2'
_cod_database_code               1575951
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.966
_shelx_estimated_absorpt_t_min   0.378
_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 bond restraints
 C17, N1, C12, C36, C10, C42, C5, C14, H10, C22, C54, C7, C41, O3, C16, C29,
 H54, C37, H7, C35, H41, C33, C8, C50, C26, C21, C49, C51, H33, C52, C40, C46,
 C30, H21, H49A, H49B, H49C, H51A, H51B, H51C, C27, C43, H40, C48, C24, C32,
 C20, C23, H43, C11, H48, C15, C6, H32, C28, H23, C47, H11, H15, C4, C34, C2,
 H47, C1, H4, C38, H2, C19, N2, C18, C9, H19, C44, C39, O1, H44, C31, H39, C3,
 C45, C25, H17A, H17B, H17C, H45, H25A, H25B, H25C
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C10(H10), C39(H39), C45(H45), C44(H44), C32(H32), C40(H40), C48(H48),
 C54(H54), C7(H7), C15(H15), C2(H2), C33(H33), C19(H19), C41(H41), C21(H21),
 C43(H43), C11(H11), C23(H23), C47(H47)
3.b Fitted hexagon refined as free rotating group:
 C18(C39,C3,C45,C31,C44)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C49(H49A,H49B,H49C), C25(H25A,H25B,H25C), C51(H51A,H51B,
 H51C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              19881
_shelx_fab_checksum              2961
_olex2_submission_special_instructions 'No special instructions were received'