Tailoring the π-system of benzimidazole ligands towards stable light-harvesting cyclometalated iridium(III) complexes
Tatarin, Sergei V.; Smirnov, Daniil E.; Taydakov, Ilya V.; Metlin, Mikhail T.; Emets, Victor; Bezzubov, Stanislav; Dalton Transactions  (2023) –; doi:10.1039/D3DT00200D

data_7712820
_publ_section_title
;
 Tailoring the \p-system of benzimidazole ligands towards stable
 light-harvesting cyclometalated iridium(III) complexes
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00200D
_journal_year                    2023
_chemical_formula_moiety         'C61 H40 Ir N4 O4 S'
_chemical_formula_sum            'C61 H40 Ir N4 O4 S'
_chemical_formula_weight         1117.23
_chemical_temperature_decomposition 593
_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     dual
_audit_creation_date             2022-01-18
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2022-01-19 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 126.9190(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.8571(14)
_cell_length_b                   15.6822(9)
_cell_length_c                   18.7424(19)
_cell_measurement_reflns_used    3889
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      22.94
_cell_measurement_theta_min      2.47
_cell_volume                     6076.1(8)
_computing_cell_refinement       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_collection       'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction        'SAINT v8.38A (Bruker AXS, 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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150.0
_diffrn_detector                 'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       '3-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       \w-scan
_diffrn_radiation_monochromator  'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0706
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14698
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         1.970
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\mS microsource'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.276
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0729 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8520.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_description       needle
_exptl_crystal_F_000             2236
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CH2Cl2, CH3OH'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         2.241
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5337
_refine_ls_number_restraints     130
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0602
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1130P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4139
_reflns_number_total             5337
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00200d2.cif
_cod_data_source_block           st321
_cod_depositor_comments
;
The following automatic conversions were performed:

data name '_chemical_melting_point' was changed to
'_chemical_temperature_decomposition' since the value had been '593
dec.'. The value '593 dec.' was changed to '593'.

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' 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 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7712820
_shelx_shelxl_version_number     2018/3
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_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
 S1-C29 = S1-C26
 1.7 with sigma of 0.01
 C36-O1
 1.2 with sigma of 0.02
 C36-O2 = O2-C37
 1.4 with sigma of 0.01
 C27-C26 = C29-C28
 1.34 with sigma of 0.02
 C27-C28
 1.4 with sigma of 0.02
 S1-C29
 1.7 with sigma of 0.02
 C36-C34
 1.4 with sigma of 0.02
 S1-C26
 1.7 with sigma of 0.02
 C27-C26
 1.35 with sigma of 0.02
 O1-O2
 2.2 with sigma of 0.01
 C37-O1
 2.7 with sigma of 0.02
 C36-C37
 2.3 with sigma of 0.04
 C25-C30 \\sim C25-C26
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C30 \\sim C31 \\sim C32 \\sim C33 \\sim C34 \\sim C35: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(O2) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.025 and sigma for
terminal atoms of 0.05
Uanis(C26) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(S1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms
of 0.2
Uanis(S1) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C31) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C30) \\sim Ueq: with sigma of 0.05 and
sigma for terminal atoms of 0.1
Uanis(O2) = Uanis(O1) = Uanis(C37) = Uanis(C36)
Uanis(C26) = Uanis(C27) = Uanis(C28) = Uanis(C29)
Uanis(C30) = Uanis(C35) = Uanis(C34)
4. Others
 Fixed Sof: H7(0.5) C26(0.5) C31(0.5) H31(0.5) C32(0.5) H32(0.5) C33(0.5)
 H33(0.5) C34(0.5) C35(0.5) H35(0.5) C30(0.5) C27(0.5) H27(0.5) C28(0.5)
 H28(0.5) S1(0.5) C29(0.5) H29(0.5) O2(0.5) C36(0.5) O1(0.5) C37(0.5) H37A(0.5)
 H37B(0.5) H37C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C21(H21), C20(H20), C19(H19), C3(H3), C17(H17), C13(H13), C8(H8),
 C2(H2), C7(H7), C16(H16), C14(H14), C5(H5), C6(H6), C15(H15), C24(H24),
 C31(H31), C32(H32), C33(H33), C35(H35), C27(H27), C28(H28), C29(H29)
5.b Fitted hexagon refined as free rotating group:
 C31(C32,C33,C34,C35,C30)
5.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              89421
_shelx_hkl_checksum              54306
_shelx_fab_checksum              47812
_olex2_submission_special_instructions 'No special instructions were received'