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_7719190
_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 H32 F4 Ir N7 O4'
_chemical_formula_sum            'C58 H32 F4 Ir N7 O4'
_chemical_formula_weight         1159.10
_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
_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                90
_cell_angle_beta                 121.61(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.018(11)
_cell_length_b                   14.807(9)
_cell_length_c                   22.779(9)
_cell_measurement_reflns_used    7788
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.3322
_cell_measurement_theta_min      2.4332
_cell_volume                     5750(6)
_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      100.01
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.999
_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  0.1101
_diffrn_reflns_av_unetI/netI     0.1038
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            35636
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.100
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    2.383
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2296
_refine_diff_density_max         1.789
_refine_diff_density_min         -1.672
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     716
_refine_ls_number_reflns         10127
_refine_ls_number_restraints     393
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.1238
_refine_ls_R_factor_gt           0.0668
_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^)+(0.0974P)^2^+3.1049P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5935
_reflns_number_total             10127
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5dt01237f2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7719190--7719192.cif.'
_cod_original_cell_volume        5750(5)
_cod_database_code               7719190
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Restrained distances
 F1-C1 \\sim F1A-C1A
 with sigma of 0.02
 F2-C5 \\sim F2A-C5A
 with sigma of 0.02
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
 C6-C1 \\sim C6A-C1A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7
 with sigma of 0.02
 C5-C4 \\sim C5A-C4A
 with sigma of 0.02
 C4-C2 \\sim C4A-C2A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C3-C1 \\sim C3A-C1A
 with sigma of 0.02
 F1-C6 \\sim F1A-C6A
 with sigma of 0.04
 F1-C3 \\sim F1A-C3A
 with sigma of 0.04
 F2-C6 \\sim F2A-C6A
 with sigma of 0.04
 F2-C4 \\sim F2A-C4A
 with sigma of 0.04
 C6-C4 \\sim C6A-C4A
 with sigma of 0.04
 C6-C3 \\sim C6A-C3A
 with sigma of 0.04
 C5-C2 \\sim C5A-C2A
 with sigma of 0.04
 C5-C1 \\sim C5A-C1A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7
 with sigma of 0.04
 C4-C3 \\sim C4A-C3A
 with sigma of 0.04
 C2-C1 \\sim C2A-C1A
 with sigma of 0.04
 C1-C7 \\sim C1A-C7
 with sigma of 0.04
2. Rigid bond restraints
 F1, F2, C6, C5, C4, C2, C3, C1, F2A, C6A, C5A, C4A, C2A, C3A, C1A, F1A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim C6 \\sim C5 \\sim C4 \\sim C2 \\sim C3 \\sim C1 \\sim F2A
\\sim C6A \\sim C5A \\sim C4A \\sim C2A \\sim C3A \\sim C1A \\sim F1A: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C4) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C1)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C5A) \\sim Ueq,
Uanis(C4A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C1A)
\\sim Ueq, Uanis(F1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Sof(F2A)=Sof(C5A)=Sof(C4A)=Sof(H4A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=
 Sof(C1A)=Sof(C6A)=Sof(F1A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(C6)=Sof(C5)=Sof(C4)=Sof(H4)=Sof(C2)=Sof(H2)=Sof(C3)=
 Sof(H3)=Sof(C1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C3(H3), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17),
 C20(H20), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29),
  C30(H30), C37(H37), C40(H40), C41(H41), C42(H42), C43(H43), C46(H46),
 C48(H48), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C54(H54), C55(H55),
  C56(H56), C4A(H4A), C2A(H2A), C3A(H3A)
5.b Fitted hexagon refined as free rotating group:
 C6(C5,C4,C2,C3,C1), C5A(C4A,C2A,C3A,C1A,C6A)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              68895
_shelx_hkl_checksum              26329
_shelx_fab_checksum              69260
_olex2_submission_special_instructions 'No special instructions were received'