The deeper it goes, the brighter it glows: NIR emissive nitro-terrylene diimides with deep LUMOs.
Mehra, Kundan Singh; Jha, Shivangee; Menon, Anila M.; Chopra, Deepak; Sankar, Jeyaraman; Chemical science 14 (2023) 3147–3153; doi:10.1039/d2sc06162g

data_1568355
_publ_section_title
;
 The deeper it goes, the brighter it glows: NIR emissive nitro-terrylene
 diimides with deep LUMOs.
;
_journal_issue                   12
_journal_name_full               'Chemical science'
_journal_page_first              3147
_journal_page_last               3153
_journal_paper_doi               10.1039/d2sc06162g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C58 H43 N5 O10'
_chemical_formula_sum            'C58 H43 N5 O10'
_chemical_formula_weight         969.97
_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             2022-06-03
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-30 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                100.242(6)
_cell_angle_beta                 95.440(6)
_cell_angle_gamma                96.856(7)
_cell_formula_units_Z            1
_cell_length_a                   8.7404(11)
_cell_length_b                   9.8973(14)
_cell_length_c                   15.641(2)
_cell_measurement_reflns_used    6974
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.36
_cell_volume                     1312.6(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1360
_diffrn_reflns_av_unetI/netI     0.2754
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16099
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_min         2.112
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.3872
_exptl_absorpt_correction_T_min  0.2333
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1317 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.6025.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear greenish blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6375
_refine_ls_number_restraints     354
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.2968
_refine_ls_R_factor_gt           0.1396
_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          0.3880
_refine_ls_wR_factor_ref         0.4474
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2044
_reflns_number_total             6375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06162g3.cif
_cod_data_source_block           TDI_N3
_cod_depositor_comments
'Adding full bibliography for 1568354--1568358.cif.'
_cod_database_code               1568355
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.978
_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. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.002 and sigma
for terminal atoms of 0.004 within 2A
3. Others
 Fixed Sof: N2(0.5) O3(0.5) O4(0.5) C19A(0.5) C20A(0.5) C14B(0.5) C18B(0.5)
 H18B(0.5) C19B(0.5) H19B(0.5) C20B(0.5) C14A(0.5) C18A(0.5) H18A(0.5)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C10(H10)
4.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C26(H26), C24(H24), C7(H7), C8(H8), C6(H6), C18B(H18B), C19B(H19B),
 C18A(H18A)
4.c Fitted hexagon refined as free rotating group:
 C15(C14B,C18B,C19B,C20B,C21)
4.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C12(H12B,H12A,H12C), C11(H11A,H11B,H11C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              76860
_shelx_fab_checksum              49132
_olex2_submission_original_sample_id TDI_N3
_olex2_submission_special_instructions 'No special instructions were received'