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_7712825
_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         'C108 H68 Cl2 Ir2 N8'
_chemical_formula_sum            'C108 H68 Cl2 Ir2 N8'
_chemical_formula_weight         1933.00
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-01-19
_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                 110.7000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.7610(10)
_cell_length_b                   18.6141(8)
_cell_length_c                   25.9710(11)
_cell_measurement_reflns_used    9462
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      26.36
_cell_measurement_theta_min      2.20
_cell_volume                     10292.9(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 2018/2 (Sheldrick, 2018)'
_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  0.0411
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            53307
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.649
_diffrn_reflns_theta_min         1.839
_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    2.681
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0785 before and 0.0452 after correction.
The Ratio of minimum to maximum transmission is 0.7946.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_description       plate
_exptl_crystal_F_000             3840
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH3CN'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.797
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1057
_refine_ls_number_reflns         19333
_refine_ls_number_restraints     317
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0924
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14631
_reflns_number_total             19333
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00200d2.cif
_cod_data_source_block           st229
_cod_depositor_comments
;
The following automatic conversions were performed:

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               7712825
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.900
_shelx_estimated_absorpt_t_min   0.590
_computing.bruker_data_scaling   'SADABS V2012/1 (Bruker AXS Inc.)'
_olex2_refinement_description
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1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 N2-C0 \\sim N2-C16
 with sigma of 0.02
 N01N-C1I \\sim N01N-C69
 with sigma of 0.02
 N01N-C1F \\sim N01N-C66
 with sigma of 0.02
 N009-C1A \\sim N009-C61
 with sigma of 0.02
 N00A-C1M \\sim N00A-C55
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C73 \\sim C74 \\sim C75 \\sim C76 \\sim C77 \\sim C17 \\sim C21 \\sim C18 \\sim
C20 \\sim C19: within 2A with sigma of 0.05 and sigma for terminal atoms of 0.1
within 2A
C61 \\sim C66 \\sim C62 \\sim C63 \\sim C64 \\sim C65 \\sim C1A \\sim C1B \\sim
C1C \\sim C1D \\sim C1E \\sim C1F: within 2A with sigma of 0.05 and sigma for
terminal atoms of 0.1 within 2A
Uanis(C72) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C0) = Uanis(C16)
Uanis(C66) = Uanis(C1F) = Uanis(C61) = Uanis(C1A)
Uanis(C61) = Uanis(C62) = Uanis(C64)
Uanis(C1G) = Uanis(C1I) = Uanis(C1K) = Uanis(C1L) = Uanis(C1J) = Uanis(C1H)
Uanis(C55) = Uanis(C1N) = Uanis(C1Q) = Uanis(C1R) = Uanis(C1P) = Uanis(C57) =
Uanis(C56) = Uanis(C59) = Uanis(C60) = Uanis(C58) = Uanis(C1O) = Uanis(C1M)
Uanis(C73) = Uanis(C75) = Uanis(C77)
4. Others
 Fixed Sof: C55(0.75) C1N(0.75) H1N(0.75) C1Q(0.75) H1Q(0.75) C1R(0.75)
 H1R(0.75) C1P(0.75) H1P(0.75) C57(0.75) H57(0.75) C56(0.25) H56(0.25)
 C59(0.25) H59(0.25) C60(0.25) H60(0.25) C58(0.25) H58(0.25) C1O(0.25)
 H1O(0.25) C1M(0.25) C0(0.5) C73(0.5) H73(0.5) C75(0.5) H75(0.5) C77(0.5)
 H77(0.5) C76(0.5) H76(0.5) C74(0.5) H74(0.5) C67(0.5) H67(0.5) C69(0.5)
 C71(0.5) H71(0.5) C72(0.5) H72(0.5) C70(0.5) H70(0.5) C68(0.5) H68(0.5)
 C61(0.5) C62(0.5) H62(0.5) C64(0.5) H64(0.5) C65(0.5) H65(0.5) C63(0.5)
 H63(0.5) C66(0.5) C16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5)
 H19(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5) C1A(0.5) C1B(0.5) H1B(0.5)
 C1D(0.5) H1D(0.5) C1E(0.5) H1E(0.5) C1C(0.5) H1C(0.5) C1F(0.5) C1G(0.5)
 H1G(0.5) C1I(0.5) C1K(0.5) H1K(0.5) C1L(0.5) H1L(0.5) C1J(0.5) H1J(0.5)
 C1H(0.5) H1H(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C50(H50), C51(H51), C53(H53), C3(H3), C2(H2), C00S(H00S), C00Z(H00Z),
 C52(H52), C39(H39), C015(H015), C31(H31), C48(H48), C26(H26), C29(H29),
 C44(H44), C30(H30), C4(H4), C25(H25), C37(H37), C01P(H01P), C34(H34), C35(H35),
  C12(H12), C7(H7), C01V(H01V), C1N(H1N), C1Q(H1Q), C1R(H1R), C1P(H1P),
 C57(H57), C01Y(H01Y), C020(H020), C45(H45), C023(H023), C47(H47), C56(H56),
 C59(H59), C60(H60), C58(H58), C1O(H1O), C36(H36), C24(H24), C46(H46),
 C02A(H02A), C73(H73), C75(H75), C77(H77), C76(H76), C74(H74), C02E(H02E),
 C23(H23), C02G(H02G), C67(H67), C71(H71), C72(H72), C70(H70), C68(H68),
 C02J(H02J), C62(H62), C64(H64), C65(H65), C63(H63), C02P(H02P), C02Q(H02Q),
 C8(H8), C02U(H02U), C02W(H02W), C10(H10), C9(H9), C030(H030), C036(H036),
 C03B(H03B), C03G(H03G), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21),
 C1B(H1B), C1D(H1D), C1E(H1E), C1C(H1C), C1G(H1G), C1K(H1K), C1L(H1L), C1J(H1J),
  C1H(H1H)
5.b Fitted hexagon refined as free rotating group:
 C55(C1N,C1Q,C1R,C1P,C57), C56(C59,C60,C58,C1O,C1M), C0(C73,C75,C77,C76,C74),
 C67(C69,C71,C72,C70,C68), C61(C62,C64,C65,C63,C66), C16(C17,C18,C19,C20,C21),
 C1A(C1B,C1D,C1E,C1C,C1F), C1G(C1I,C1K,C1L,C1J,C1H)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              10894
_shelx_hkl_checksum              706
_shelx_fab_checksum              37341
_olex2_submission_special_instructions 'No special instructions were received'