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_1568358
_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         '2(C58 H44 N4 O8), C H Cl3'
_chemical_formula_sum            'C117 H89 Cl3 N8 O16'
_chemical_formula_weight         1969.31
_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             2022-08-05
_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                86.235(7)
_cell_angle_beta                 85.355(2)
_cell_angle_gamma                89.587(9)
_cell_formula_units_Z            2
_cell_length_a                   9.412(2)
_cell_length_b                   23.109(16)
_cell_length_c                   30.268(10)
_cell_measurement_reflns_used    1416
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      16.85
_cell_measurement_theta_min      2.46
_cell_volume                     6548(5)
_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 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.9119
_diffrn_reflns_av_unetI/netI     0.5137
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            169920
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.191
_diffrn_reflns_theta_max         25.191
_diffrn_reflns_theta_min         1.766
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.3320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1601 before and 0.0929 after correction.
The Ratio of minimum to maximum transmission is 0.4455.
The \l/2 correction factor is Not present.
;
_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    0.999
_exptl_crystal_description       plate
_exptl_crystal_F_000             2052
_exptl_crystal_size_max          0.102
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1332
_refine_ls_number_reflns         23329
_refine_ls_number_restraints     1032
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.3913
_refine_ls_R_factor_gt           0.1584
_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          0.4012
_refine_ls_wR_factor_ref         0.5390
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4205
_reflns_number_total             23329
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06162g3.cif
_cod_data_source_block           tdi_n2_iii
_cod_depositor_comments
'Adding full bibliography for 1568354--1568358.cif.'
_cod_database_code               1568358
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.987
_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(O11A)=Sof(O12A)=1-FVAR(1)
 Sof(O11)=Sof(O12)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C61(H61), C56(H56), C10(H10), C114(H114), C68(H68), C3(H3), C107(H107),
 C49(H49), C117(H117)
4.b Aromatic/amide H refined with riding coordinates:
 C18(H18), C64(H64), C102(H102), C101(H101), C66(H66), C97(H97), C92(H92),
 C24(H24), C76(H76), C65(H65), C110(H110), C43(H43), C19(H19), C29(H29),
 C28(H28), C112(H112), C53(H53), C111(H111), C34(H34), C8(H8), C54(H54),
 C82(H82), C39(H39), C7(H7), C91(H91), C81(H81), C33(H33), C6(H6), C38(H38),
 C87(H87), C86(H86), C52(H52)
4.c Idealised Me refined as rotating group:
 C58(H58A,H58B,H58C), C51(H51A,H51B,H51C), C50(H50A,H50B,H50C), C63(H63A,H63B,
 H63C), C57(H57A,H57B,H57C), C115(H11A,H11B,H11C), C116(H11D,H11E,H11F),
 C62(H62A,H62B,H62C), C12(H12A,H12B,H12C), C4(H4A,H4B,H4C), C11(H11G,H11H,H11I),
  C5(H5A,H5B,H5C), C109(H10A,H10B,H10C), C108(H10D,H10E,H10F), C69(H69A,H69B,
 H69C), C70(H70A,H70B,H70C)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 639 electrons were 
found in a volume of 2393\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 4[CHCl3], 2[C6H14] per Formula Unit 
which account for 664 electrons per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              72357
_shelx_fab_checksum              71307
_olex2_submission_special_instructions 'No special instructions were received'