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_1568354
_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_absolute_configuration unk
_chemical_formula_moiety         'C58 H44 N4 O8, 2(C H Cl3)'
_chemical_formula_sum            'C60 H46 Cl6 N4 O8'
_chemical_formula_weight         1163.71
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-09-24
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-09-26 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4750(15)
_cell_length_b                   22.912(2)
_cell_length_c                   31.837(3)
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      29.58
_cell_measurement_theta_min      2.19
_cell_volume                     10558.8(17)
_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    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      120.0
_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  0.2655
_diffrn_reflns_av_unetI/netI     0.1954
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            182524
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.099
_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.2528
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1725 before and 0.1133 after correction.
The Ratio of minimum to maximum transmission is 0.3389.
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    1.464
_exptl_crystal_description       needle
_exptl_crystal_F_000             4800
_exptl_crystal_size_max          0.092
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.128
_refine_ls_abs_structure_details
;
 Flack x determined using 4442 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1404
_refine_ls_number_reflns         26200
_refine_ls_number_restraints     1071
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1825
_refine_ls_R_factor_gt           0.1111
_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^)+(0.0855P)^2^+38.8843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2443
_refine_ls_wR_factor_ref         0.2831
_reflns_Friedel_coverage         0.964
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                15007
_reflns_number_total             26200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc06162g3.cif
_cod_data_source_block           TDI_N2_I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'DIRECT' was changed
to 'direct' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1568354--1568358.cif.
;
_cod_original_cell_volume        10558.5(18)
_cod_database_code               1568354
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.965
_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. Restrained distances
 Cl7-C119 \\sim Cl7A-C119
 with sigma of 0.02
 Cl9-C119 \\sim Cl9A-C119
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.001 and sigma
for terminal atoms of 0.002 within 2A
4. Others
 Sof(Cl7A)=Sof(Cl9A)=1-FVAR(1)
 Sof(Cl7)=Sof(Cl9)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C62(H62), C120(H120), C107(H107), C9(H9), C67(H67), C49(H49),
 C56(H56), C118(H118), C114(H114), C117(H117), C119(H119)
5.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C29(H29), C24(H24), C38(H38), C34(H34), C18(H18), C92(H92),
 C87(H87), C54(H54), C76(H76), C39(H39), C86(H86), C33(H33), C91(H91), C53(H53),
  C82(H82), C12(H12), C97(H97), C96(H96), C110(H110), C111(H111), C112(H112),
 C60(H60), C59(H59), C70(H70), C1(H1), C102(H102), C2(H2), C52(H52), C44(H44),
 C43(H43), C101(H101)
5.c Fitted hexagon refined as free rotating group:
 C74(C73,C79,C80,C81,C82), C113(C105,C106,C110,C111,C112), C61(C60,C59,C70,C66,
 C65)
5.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C11(H11A,H11B,H11C), C5(H5A,H5B,H5C), C68(H68A,H68B,H68C),
 C64(H64A,H64B,H64C), C10(H10A,H10B,H10C), C63(H63A,H63B,H63C), C69(H69A,H69B,
 H69C), C57(H57A,H57B,H57C), C51(H51A,H51B,H51C), C116(H11D,H11E,H11F),
 C108(H10D,H10E,H10F), C115(H11G,H11H,H11I), C109(H10G,H10H,H10I), C50(H50A,
 H50B,H50C), C58(H58A,H58B,H58C)
;
_shelx_res_checksum              90799
_olex2_submission_special_instructions 'No special instructions were received'