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_7712831
_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, 4(C7 H8), 3.75(C2 H3 N)'
_chemical_formula_sum            'C143.5 H111.25 Cl2 Ir2 N11.75'
_chemical_formula_weight         2455.49
_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     iterative
_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
;
2022-12-23 deposited with the CCDC.	2023-04-19 downloaded from the CCDC.
;
_cell_angle_alpha                112.254(2)
_cell_angle_beta                 90.911(2)
_cell_angle_gamma                93.085(2)
_cell_formula_units_Z            2
_cell_length_a                   17.2379(10)
_cell_length_b                   17.7094(11)
_cell_length_c                   19.7481(12)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      31.52
_cell_measurement_theta_min      2.23
_cell_volume                     5567.1(6)
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON II'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type            'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_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  0.0262
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            220131
_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         29.000
_diffrn_reflns_theta_min         2.101
_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    2.497
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6323
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0612 before and 0.0408 after correction.
The Ratio of minimum to maximum transmission is 0.8474.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             2485
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene, CH3CN'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.922
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1418
_refine_ls_number_reflns         29585
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0201
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0172P)^2^+8.0347P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0501
_reflns_Friedel_coverage         0.000
_reflns_number_gt                27165
_reflns_number_total             29585
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00200d2.cif
_cod_data_source_block           st229neo
_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_original_formula_sum        'C143.50 H111.25 Cl2 Ir2 N11.75'
_cod_database_code               7712831
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.676
_shelx_estimated_absorpt_t_min   0.635
_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
 C63-C62 = C61-C60
 1.45 with sigma of 0.02
 N5-C61
 1.15 with sigma of 0.02
 N0-C63
 1.15 with sigma of 0.02
 C69-C55 \\sim C71-C59
 with sigma of 0.02
 C61-C60 \\sim C63-C62
 with sigma of 0.01
 N5-C61 \\sim N0-C63
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uiso(C62) = Uiso(C63) = Uiso(N0)
Uiso(C69) = Uiso(C55) = Uiso(C0) = Uiso(C65) = Uiso(C67) = Uiso(C66) = Uiso(C68)
Uiso(C71) = Uiso(C70) = Uiso(C72) = Uiso(C57) = Uiso(C56) = Uiso(C58) =
Uiso(C59)
4. Others
 Fixed Sof: C64(0.75) H64A(0.75) H64B(0.75) H64C(0.75) N0(0.45) C55(0.4)
 C0(0.4) H0(0.4) C65(0.4) H65(0.4) C67(0.4) H67(0.4) C66(0.4) H66(0.4) C68(0.4)
 H68(0.4) C61(0.55) C60(0.55) H60A(0.55) H60B(0.55) H60C(0.55) C69(0.4)
 H69A(0.4) H69B(0.4) H69C(0.4) C58(0.6) H58(0.6) C71(0.6) C70(0.6) H70(0.6)
 C72(0.6) H72(0.6) C57(0.6) H57(0.6) C56(0.6) H56(0.6) C59(0.6) H59A(0.6)
 H59B(0.6) H59C(0.6) C62(0.45) H62A(0.45) H62B(0.45) H62C(0.45) C63(0.45)
 N5(0.55) C1A(0.75) N6(0.75)
5.a Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C52(H52), C25(H25), C53(H53), C00X(H00X), C29(H29), C012(H012),
 C014(H014), C26(H26), C018(H018), C019(H019), C01A(H01A), C01B(H01B),
 C01C(H01C), C50(H50), C01E(H01E), C51(H51), C01J(H01J), C01N(H01N), C01P(H01P),
  C12(H12), C01U(H01U), C01V(H01V), C24(H24), C01Y(H01Y), C01Z(H01Z), C2(H2),
 C021(H021), C023(H023), C23(H23), C44(H44), C17(H17), C39(H39), C02B(H02B),
 C3(H3), C30(H30), C02G(H02G), C02I(H02I), C02J(H02J), C02K(H02K), C45(H45),
 C02M(H02M), C48(H48), C10(H10), C02Q(H02Q), C02R(H02R), C34(H34), C02T(H02T),
 C4(H4), C7(H7), C18(H18), C21(H21), C31(H31), C02Z(H02Z), C030(H030), C9(H9),
 C032(H032), C033(H033), C034(H034), C8(H8), C036(H036), C19(H19), C039(H039),
 C03A(H03A), C03B(H03B), C03C(H03L), C46(H46), C03F(H03F), C35(H35), C47(H47),
 C03J(H03J), C03K(H03K), C37(H37), C36(H36), C20(H20), C03O(H03O), C03P(H03P),
 C03R(H03R), C03S(H03S), C03T(H03T), C03U(H03U), C03Z(H03Z), C040(H040), C0(H0),
  C65(H65), C67(H67), C66(H66), C68(H68), C58(H58), C70(H70), C72(H72),
 C57(H57), C56(H56)
5.b Fitted hexagon refined as free rotating group:
 C55(C0,C65,C67,C66,C68), C58(C71,C70,C72,C57,C56)
5.c Idealised Me refined as rotating group:
 C03I(H03C,H03D,H03E), C03Q(H03M,H03N,H03Q), C03W(H03G,H03H,H03I), C64(H64A,
 H64B,H64C), C046(H04A,H04B,H04C), C048(H04D,H04E,H04F), C60(H60A,H60B,H60C),
 C69(H69A,H69B,H69C), C59(H59A,H59B,H59C), C62(H62A,H62B,H62C)
;
_shelx_res_checksum              84413
_shelx_hkl_checksum              17474
_olex2_submission_special_instructions 'No special instructions were received'