Sulfonyl-Substituted Heteroleptic Cyclometalated Iridium(III) Complexes as Blue Emitters for Solution-Processable Phosphorescent Organic Light-Emitting Diodes.
Benjamin, Helen; Zheng, Yonghao; Batsanov, Andrei S.; Fox, Mark A.; Al-Attar, Hameed A; Monkman, Andrew P.; Bryce, Martin R.; Inorganic chemistry 55 (2016) 8612–8627; doi:10.1021/acs.inorgchem.6b01179

data_4348463
_publ_section_title
;
 Sulfonyl-Substituted Heteroleptic Cyclometalated Iridium(III) Complexes
 as Blue Emitters for Solution-Processable Phosphorescent Organic
 Light-Emitting Diodes.
;
_journal_issue                   17
_journal_name_full               'Inorganic chemistry'
_journal_page_first              8612
_journal_page_last               8627
_journal_paper_doi               10.1021/acs.inorgchem.6b01179
_journal_volume                  55
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C48 H40 F4 Ir N3 O6 S2, 2.75(C H2 Cl2)'
_chemical_formula_sum            'C50.75 H45 Cl5.5 F4 Ir N3 O6 S2'
_chemical_formula_weight         1320.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-10-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9904(8)
_cell_length_b                   28.4675(13)
_cell_length_c                   11.4762(5)
_cell_measurement_reflns_used    9025
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.21
_cell_measurement_theta_min      2.40
_cell_volume                     5550.7(4)
_computing_cell_refinement       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_collection       'APEX2 v.2013.4_1 (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.30C (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS 2013/1 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '3-circle area detector 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  0.0528
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            68389
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.588
_diffrn_reflns_theta_min         2.280
_diffrn_source                   'ImuS microsource'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.808
_exptl_absorpt_correction_T_max  0.4104
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2009/1 (Bruker,2010) was used for absorption correction.
wR2(int) was 0.1183 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.8382.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       trapetsoid
_exptl_crystal_F_000             2628
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.631
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.132
_refine_ls_abs_structure_details
;
 Flack x determined using 5820 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
 By conventional hole-in-one fit to all intensities, x=0.013(6).
 Hooft parameter y=0.012(3). 
;
_refine_ls_abs_structure_Flack   0.016(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     694
_refine_ls_number_reflns         16991
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0400P)^2^+0.6530P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0868
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                14645
_reflns_number_total             16991
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            12.cif
_cod_data_source_block           12
_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/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C50.75 H45 Cl5.50 F4 Ir N3 O6 S2'
_cod_database_code               4348463
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Cl6-Cl5
 3 with sigma of 0.02
 Cl6-C51 = Cl5-C51
 1.7 with sigma of 0.02
 Cl2B-C49B \\sim Cl2A-C49A
 with sigma of 0.02
 Cl1-C49B \\sim Cl1-C49A
 with sigma of 0.02
 Cl4B-C50B \\sim Cl4A-C50A \\sim Cl3-C50B \\sim Cl3-C50A
 with sigma of 0.02
 S2A-O6B \\sim S2A-O5B \\sim S2B-O6A \\sim S2B-O5A
 with sigma of 0.02
 S2B-C39B \\sim S2A-C39A
 with sigma of 0.02
 Cl6-C51 \\sim Cl5-C51
 with sigma of 0.02
 Cl8A-C53B \\sim Cl8B-C53A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(C50B) = Uiso(C50A)
Uanis(S2A) = Uanis(S2B)
Uiso(C44B) = Uiso(C44A)
Uanis(C48A) = Uanis(C48B)
Uiso(C51) = Uiso(Cl6)
Uiso(C45B) = Uiso(C45A)
Uiso(C53A) = Uiso(C53B)
Uiso(Cl8B) = Uiso(Cl8A)
4. Others
 Fixed Sof: S2A(0.45) S2B(0.55) O5A(0.55) O5B(0.45) O6A(0.55) O6B(0.45)
 C39A(0.45) H39A(0.45) H39B(0.45) H39C(0.45) C39B(0.55) H39D(0.55) H39E(0.55)
 H39F(0.55) C44A(0.55) H44A(0.55) C44B(0.45) H44B(0.45) C45B(0.45) C45A(0.55)
 C48A(0.55) H48A(0.55) H48B(0.55) H48C(0.55) C48B(0.45) H48D(0.45) H48E(0.45)
 H48F(0.45) Cl2A(0.6) Cl2B(0.4) C49A(0.6) H49A(0.6) H49B(0.6) C49B(0.4)
 H49C(0.4) H49D(0.4) Cl4A(0.8) Cl4B(0.2) C50A(0.8) H50A(0.8) H50B(0.8)
 C50B(0.2) H50C(0.2) H50D(0.2) Cl5(0.5) Cl6(0.5) C51(0.5) H51A(0.5) H51B(0.5)
 Cl7(0.15) C53A(0.1) Cl8B(0.2) Cl8A(0.15) C53B(0.15)
5.a Secondary CH2 refined with riding coordinates:
 C49A(H49A,H49B), C49B(H49C,H49D), C50A(H50A,H50B), C50B(H50C,H50D), C51(H51A,
 H51B)
5.b Me refined with riding coordinates:
 C39A(H39A,H39B,H39C), C39B(H39D,H39E,H39F)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C16(H16), C17(H17),
 C19(H19), C25(H25), C27(H27), C28(H28), C32(H32), C34(H34), C42(H42),
 C44A(H44A), C44B(H44B)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C36(H36A,H36B,H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48A(H48A,H48B,H48C),
 C48B(H48D,H48E,H48F)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'