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_1568357
_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 H44 N4 O8'
_chemical_formula_sum            'C58 H44 N4 O8'
_chemical_formula_weight         924.97
_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     direct
_audit_creation_date             2022-08-03
_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                90
_cell_angle_beta                 114.589(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.736(3)
_cell_length_b                   16.294(2)
_cell_length_c                   14.3851(17)
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.09
_cell_measurement_theta_min      2.40
_cell_volume                     5698.4(12)
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0975
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            91148
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.699
_diffrn_reflns_theta_min         1.675
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.6052
_exptl_absorpt_correction_T_min  0.2049
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1583 before and 0.0905 after correction.
The Ratio of minimum to maximum transmission is 0.3386.
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    1.078
_exptl_crystal_description       plate
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.403
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.059
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         7360
_refine_ls_number_restraints     294
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0835
_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^)+(0.1349P)^2^+11.5096P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2464
_refine_ls_wR_factor_ref         0.2585
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5386
_reflns_number_total             7360
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06162g3.cif
_cod_data_source_block           tdi_n2_ii
_cod_depositor_comments
'Adding full bibliography for 1568354--1568358.cif.'
_cod_database_code               1568357
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.996
_shelx_estimated_absorpt_t_min   0.971
_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
 Sof(C11B)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12B)=Sof(H12D)=Sof(H12E)=
 Sof(H12F)=Sof(C10B)=Sof(H10B)=1-FVAR(1)
 Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12A)=
 Sof(H12A)=Sof(H12B)=Sof(H12C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C3(H3), C10A(H10A), C10B(H10B)
4.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C23(H23), C26(H26), C27(H27), C6(H6), C18(H18), C7(H7), C8(H8)
4.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C4(H4A,H4B,H4C), C11A(H11A,H11B,H11C), C12A(H12A,H12B,H12C),
 C11B(H11D,H11E,H11F), C12B(H12D,H12E,H12F)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 290 electrons were 
found in a volume of 1892\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 
1.5[C7H8] per Unit Cell 
which account for 300 electrons 
per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              65660
_shelx_fab_checksum              81136
_olex2_submission_special_instructions 'No special instructions were received'