Efficient 1-(thiophen-2-yl)isoquinoline-based ionic iridophosphors with bulky counterion for solution-processed deep-red electroluminescence
Tao, Peng; Zheng, Xiao-Kang; Jiang, He; Sheng, Xinghao; Deng, Yongjing; Chan, Yuk Yin Ian; Zhao, Qiang; Wong, Wai-Yeung Raymond; Dalton Transactions  (2023) –; doi:10.1039/D3DT02061D

data_7713574
_publ_section_title
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 Efficient 1-(thiophen-2-yl)isoquinoline-based ionic iridophosphors with
 bulky counterion for solution-processed deep-red electroluminescence
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_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT02061D
_journal_year                    2023
_chemical_formula_moiety         'C44 H40 Ir N4 S2, C32 H12 B F24, 0.5[C6H14]'
_chemical_formula_sum            'C79 H59 B F24 Ir N4 S2'
_chemical_formula_weight         1787.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-07-17
_audit_creation_method
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Olex2 1.5-dev
(compiled 2023.07.05 svn.r7b2821a9 for OlexSys, GUI svn.r6697)
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_audit_update_record
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2023-07-25 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
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_cell_angle_alpha                90
_cell_angle_beta                 95.8700(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3920(2)
_cell_length_b                   34.9915(7)
_cell_length_c                   20.6937(5)
_cell_measurement_reflns_used    9115
_cell_measurement_temperature    193.0
_cell_measurement_theta_max      68.42
_cell_measurement_theta_min      3.32
_cell_volume                     7485.4(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       Bruker
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      193.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            64942
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        66.594
_diffrn_reflns_theta_max         66.594
_diffrn_reflns_theta_min         2.490
_exptl_absorpt_coefficient_mu    4.925
_exptl_absorpt_correction_T_max  0.4672
_exptl_absorpt_correction_T_min  0.3316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1286 before and 0.0722 after correction.
The Ratio of minimum to maximum transmission is 0.7098.
The \l/2 correction factor is Not present.
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_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_description       block
_exptl_crystal_F_000             3564
_exptl_crystal_preparation       Luminescent,Luminescent
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.233
_exptl_crystal_size_min          0.155
_refine_diff_density_max         0.738
_refine_diff_density_min         -1.197
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
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 Refined as an inversion twin.
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_refine_ls_abs_structure_Flack   0.493(6)
_refine_ls_extinction_coef       0.000066(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2118
_refine_ls_number_reflns         25941
_refine_ls_number_restraints     1341
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0357
_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^)+(0.0377P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0801
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.926
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                23698
_reflns_number_total             25941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt02061d2.cif
_cod_data_source_block           111
_cod_database_code               7713574
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
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1. Twinned data refinement
 Scales: 0.507(6)
 0.493(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Uiso/Uaniso restraints and constraints
F007 \\sim F03T \\sim F04D \\sim F00B \\sim F053 \\sim F00E \\sim F05L \\sim
F00G \\sim F04H \\sim F00I \\sim F05N \\sim F00K \\sim F05V \\sim F1 \\sim F4
\\sim F00M \\sim F04C \\sim F00S \\sim F04S \\sim F013 \\sim F05F \\sim F015
\\sim F05U \\sim F018 \\sim F2 \\sim F01A \\sim F05G \\sim F01D \\sim F0 \\sim
F01T \\sim F05S \\sim F01V \\sim F045 \\sim F021 \\sim F04E \\sim F026 \\sim
F04N \\sim F02B \\sim F052 \\sim F02D \\sim F05E \\sim F02E \\sim F05K \\sim
F02F \\sim F05R \\sim F02H \\sim F05Y \\sim F02J \\sim F04I \\sim F02T \\sim
F05Z \\sim F02W \\sim F3 \\sim F036 \\sim F05O \\sim F037 \\sim F02X \\sim F03C
\\sim F02C \\sim F03F \\sim F04T \\sim F03R \\sim F03S: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
C2 \\sim C2A \\sim C3 \\sim C4 \\sim C4A \\sim C3A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 B1, F007, C01Q, F00G, C00Y, F015, C01W, C028, C02C, C020, C041, C055, C019,
 C02G, C030, F02D, F03C, F03F, C01L, C02N, C04B, C01S, C03M, C04X, C05C, C04I,
 C046, C04J, C04O, C01M, C05A, C05V, C05L, C05S, C02R, C061, C02Q, C05H, C057,
 F05E, F05U, F05Y, F05Z, F05V, F3, F01A, F02H, F00E, F05F, F05K, F05N, F05G,
 F05O, F05L, F02F, F045, F04N, F03S, F1, F021, F00I, F00S, F013
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F052, F00B, C05I, F01D, F01V, C03K, C01P, C04Q, C027, C02S, C02K, B2, C04W,
 C01N, C02X, C00X, F02E, F03T, F02J, C01Y, C014, C02P, C024, C00U, C023, C04Z,
 C032, C050, C01H, C056, C02U, C02I, C05T, C05J, C03P, C04T, C059, C033, C03E,
 C03G, F02T, F01T, F036, F04S, F053, F05R, F4, F04T, F05S, F02B, F02W, F02X, F0,
  F02C, F026, F04E, F037, F03R, F04C, F04H, F04D, F04I, F2, F018, F00K, F00M
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(F04D)=Sof(F04I)=Sof(F2)=1-FVAR(1)
 Sof(F03R)=Sof(F04C)=Sof(F04H)=FVAR(1)
 Sof(F05Z)=Sof(F05V)=Sof(F3)=1-FVAR(2)
 Sof(F05E)=Sof(F05U)=Sof(F05Y)=FVAR(2)
 Sof(F05G)=Sof(F05O)=Sof(F05L)=1-FVAR(3)
 Sof(F05F)=Sof(F05K)=Sof(F05N)=FVAR(3)
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=1-FVAR(4)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(4)
 Sof(F02X)=Sof(F0)=Sof(F02C)=1-FVAR(5)
 Sof(F026)=Sof(F02B)=Sof(F02W)=FVAR(5)
 Sof(F4)=Sof(F04T)=Sof(F05S)=1-FVAR(6)
 Sof(F04S)=Sof(F053)=Sof(F05R)=FVAR(6)
 Fixed X: Ir01(0.4597)
 Fixed Y: Ir01(0.5566)
 Fixed Z: Ir01(1.037129)
6.a Me refined with riding coordinates:
 C05M(H05G,H05H,H05I), C05X(H05J,H05K,H05L), C063(H06A,H06B,H06C), C2(H2A,H2B,
 H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,
 H3AC), C4A(H4AA,H4AB,H4AC)
6.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00U(H00U), C00V(H00V), C012(H012), C014(H014), C017(H017),
 C01C(H01C), C01E(H01E), C01F(H01F), C01G(H01G), C01K(H01K), C01L(H01L),
 C01O(H01O), C01P(H01P), C01R(H01R), C01S(H01S), C01W(H01W), C01X(H01X),
 C01Y(H01Y), C01Z(H01Z), C023(H023), C024(H024), C028(H028), C029(H029),
 C02A(H02A), C02I(H02I), C02K(H02K), C02L(H02L), C02N(H02N), C02O(H02O),
 C02P(H02P), C02Q(H02Q), C02R(H02R), C02V(H02V), C02Y(H02Y), C02Z(H02Z),
 C031(H031), C033(H033), C035(H035), C03A(H03A), C03B(H03B), C03D(H03D),
 C03J(H03J), C03L(H03L), C03M(H03M), C03N(H03N), C03P(H03P), C03Q(H03Q),
 C03V(H03V), C03Z(H03Z), C040(H040), C041(H041), C044(H044), C049(H049),
 C04A(H04A), C04B(H04N), C04D(H04E), C04F(H04F), C04K(H04K), C04Q(H04Q),
 C04R(H04R), C04V(H04V), C04X(H04X), C04Y(H04Y), C051(H051), C054(H054),
 C058(H058), C05A(H05M)
6.c Idealised Me refined as rotating group:
 C03O(H03C,H03E,H03F), C04G(H04G,H04H,H04I), C04L(H04J,H04L,H04M), C04U(H04B,
 H04C,H04D), C05P(H05A,H05B,H05C), C05Q(H05D,H05E,H05F)
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_smtbx_masks_special_details
;
A solvent mask was calculated and 104 electrons were 
found in a volume of 482\%A^3^ in 4 voids per unit cell. 
This is consistent with the presence of 0.5[C6H14] per Formula Unit 
which account for 100 electrons per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              75829
_shelx_fab_checksum              76141
_olex2_submission_special_instructions 'No special instructions were received'