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_1568356
_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 H42 N6 O12, 4(C H Cl3)'
_chemical_formula_sum            'C62 H46 Cl12 N6 O12'
_chemical_formula_weight         1492.45
_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             2022-08-03
_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                67.233(10)
_cell_angle_beta                 88.114(11)
_cell_angle_gamma                80.705(10)
_cell_formula_units_Z            1
_cell_length_a                   10.4617(15)
_cell_length_b                   12.3933(19)
_cell_length_c                   13.748(2)
_cell_measurement_reflns_used    5055
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.92
_cell_measurement_theta_min      2.50
_cell_volume                     1621.2(4)
_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      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.0642
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32219
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.034
_diffrn_reflns_theta_min         1.607
_exptl_absorpt_coefficient_mu    0.579
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0831 before and 0.0553 after correction.
The Ratio of minimum to maximum transmission is 0.9141.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear bluish green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   bluish
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       0.0078(11)
_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   0.973
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         9415
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0706P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1584
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4922
_reflns_number_total             9415
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06162g3.cif
_cod_data_source_block           tdi_n4
_cod_depositor_comments
'Adding full bibliography for 1568354--1568358.cif.'
_cod_original_cell_volume        1621.2(5)
_cod_database_code               1568356
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.943
_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. Others
 Sof(Cl4B)=Sof(Cl5B)=Sof(H31A)=Sof(Cl6B)=1-FVAR(1)
 Sof(Cl6A)=Sof(H31)=Sof(Cl5A)=Sof(Cl4A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C10(H10), C3(H3), C30(H30), C31(H31), C31(H31A)
3.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C24(H24), C28(H28), C29(H29), C7(H7), C6(H6), C8(H8)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              15343
_olex2_submission_special_instructions 'No special instructions were received'