Strategic fluorine atom positioning in carbazolyl oxadiazole derivatives: constructing asymmetric Ir(III) complexes for enhanced electroluminescence performance.
Liu, Jia-Wei; Wang, Xue-Cheng; Wen, Li-Jing; Chen, Hao-Yu; Ren, Jin-Xia; Li, Jie; Liu, Chang; Li, Yong-Hua; Chen, Bo; Wang, Shi; Zhang, Kenneth Yin; Dalton transactions (Cambridge, England : 2003) 54 (2025) 13184–13191; doi:10.1039/d5dt01237f

data_7719191
_publ_section_title
;
 Strategic fluorine atom positioning in carbazolyl oxadiazole derivatives:
 constructing asymmetric Ir(III) complexes for enhanced
 electroluminescence performance.
;
_journal_issue                   35
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              13184
_journal_page_last               13191
_journal_paper_doi               10.1039/d5dt01237f
_journal_volume                  54
_journal_year                    2025
_chemical_formula_moiety         'C58 H50 F2 Ir N7 O4'
_chemical_formula_sum            'C58 H50 F2 Ir N7 O4'
_chemical_formula_weight         1139.25
_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
_audit_creation_date             2024-07-22
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-26 deposited with the CCDC.	2025-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                99.797(7)
_cell_angle_beta                 95.993(7)
_cell_angle_gamma                117.288(5)
_cell_formula_units_Z            2
_cell_length_a                   13.554(4)
_cell_length_b                   14.306(5)
_cell_length_c                   19.189(6)
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.6543
_cell_measurement_theta_min      2.4352
_cell_volume                     3187.0(18)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16296
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.653
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.144
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.252
_refine_diff_density_min         -2.127
_refine_diff_density_rms         0.140
_refine_ls_extinction_coef       0.0031(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         11060
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0663
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0993P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7000
_reflns_number_total             11060
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01237f2.cif
_cod_data_source_block           1_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7719190--7719192.cif.'
_cod_database_code               7719191
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.830
_shelx_estimated_absorpt_t_min   0.798
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(O3) \\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,
 H25B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,H49B), C50(H50A,H50B),
 C51(H51A,H51B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C28(H28), C30(H30), C31(H31), C36(H36), C37(H37), C40(H40),
  C41(H41), C42(H42), C43(H43), C46(H46), C53(H53), C54(H54), C55(H55), C56(H56)
2.c Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C52(H52A,H52B,H52C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              10018
_shelx_hkl_checksum              43353
_shelx_fab_checksum              37643
_olex2_submission_special_instructions 'No special instructions were received'