#------------------------------------------------------------------------------
#$Date: 2019-11-24 10:03:01 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237562 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/72/7237290.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7237290
loop_
_publ_author_name
'Kwon, Youngjae'
'Han, Si Hyun'
'Yu, Seokhyeon'
'Lee, Jun Yeob'
'Lee, Kang Mun'
_publ_section_title
;
 Functionalized phenylimidazole-based facial-homoleptic iridium(iii)
 complexes and their excellent performance in blue phosphorescent organic
 light-emitting diodes
;
_journal_issue                   16
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              4565
_journal_paper_doi               10.1039/C8TC00568K
_journal_volume                  6
_journal_year                    2018
_chemical_formula_moiety         C42H58B20
_chemical_formula_sum            'C42 H58 B20'
_chemical_formula_weight         779.08
_chemical_name_common            1TP
_chemical_name_systematic        1TP
_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   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc1ky8sk
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-03-07 deposited with the CCDC.
2018-04-10 downloaded from the CCDC.
;
_cell_angle_alpha                92.668(10)
_cell_angle_beta                 97.662(10)
_cell_angle_gamma                112.396(9)
_cell_formula_units_Z            1
_cell_length_a                   8.8120(14)
_cell_length_b                   8.8274(15)
_cell_length_c                   16.566(2)
_cell_measurement_reflns_used    4099
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.242
_cell_measurement_theta_min      1.247
_cell_volume                     1174.1(3)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14244
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.193
_diffrn_reflns_theta_min         1.247
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.055
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_description       Cubic
_exptl_crystal_F_000             410
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.672
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         4099
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0817
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1539P)²+0.4853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2345
_refine_ls_wR_factor_ref         0.2853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             4099
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8tc00568k2.cif
_cod_data_source_block           1TP
_cod_database_code               7237290
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.6904(4) 0.5738(4) 0.16540(16) 0.0544(8) Uani 1 1 d . .
C2 C 0.7343(4) 0.6060(4) 0.27137(17) 0.0563(8) Uani 1 1 d . .
C3 C 0.8407(4) 0.5281(4) 0.31636(17) 0.0585(8) Uani 1 1 d . .
C4 C 0.7766(5) 0.3653(5) 0.3319(2) 0.0816(11) Uani 1 1 d . .
C5 C 0.8774(7) 0.2980(6) 0.3748(3) 0.0985(14) Uani 1 1 d . .
C6 C 1.0432(6) 0.3892(6) 0.4049(2) 0.0849(12) Uani 1 1 d . .
C7 C 1.1064(5) 0.5510(6) 0.3887(3) 0.0909(12) Uani 1 1 d . .
C8 C 1.0086(5) 0.6201(5) 0.3452(2) 0.0777(10) Uani 1 1 d . .
C9 C 0.7555(3) 0.4611(4) 0.12428(16) 0.0509(7) Uani 1 1 d . .
C10 C 0.9244(4) 0.5065(4) 0.1215(2) 0.0640(9) Uani 1 1 d . .
C11 C 0.9825(4) 0.3977(4) 0.0885(2) 0.0635(9) Uani 1 1 d . .
C12 C 0.8767(4) 0.2393(4) 0.05713(17) 0.0546(8) Uani 1 1 d . .
C13 C 0.7072(4) 0.1967(4) 0.0568(2) 0.0612(8) Uani 1 1 d . .
C14 C 0.6481(4) 0.3048(4) 0.08995(19) 0.0611(8) Uani 1 1 d . .
C15 C 0.9414(4) 0.1187(4) 0.02653(18) 0.0559(8) Uani 1 1 d . .
C16 C 1.0775(4) 0.1001(4) 0.07250(19) 0.0601(8) Uani 1 1 d . .
C17 C 0.8656(4) 0.0166(4) -0.04610(18) 0.0608(8) Uani 1 1 d . .
C18 C 1.1522(7) 0.3124(8) 0.4484(3) 0.1272(19) Uani 1 1 d . .
H18A H 1.0913 0.2390 0.4853 0.153 Uiso 1 1 calc R U
H18B H 1.2489 0.3983 0.4811 0.153 Uiso 1 1 calc R U
C19 C 1.2090(7) 0.2170(7) 0.3900(5) 0.155(3) Uani 1 1 d D .
H19A H 1.2711 0.2896 0.3532 0.186 Uiso 1 1 calc R U
H19B H 1.1132 0.1298 0.3575 0.186 Uiso 1 1 calc R U
C20 C 1.3242(14) 0.1392(14) 0.4408(8) 0.264(5) Uani 1 1 d D U
H20A H 1.4283 0.2221 0.4694 0.317 Uiso 1 1 calc R U
H20B H 1.2673 0.0650 0.4784 0.317 Uiso 1 1 calc R U
C21 C 1.345(3) 0.051(2) 0.3671(13) 0.459(12) Uani 1 1 d D U
H21A H 1.4609 0.0918 0.3621 0.689 Uiso 1 1 calc R U
H21B H 1.2832 0.0703 0.3192 0.689 Uiso 1 1 calc R U
H21C H 1.3053 -0.0645 0.3724 0.689 Uiso 1 1 calc R U
H1 H 1.135(4) 0.168(4) 0.1260(19) 0.061(8) Uiso 1 1 d . .
H2 H 0.772(4) 0.027(4) -0.0776(19) 0.064(9) Uiso 1 1 d . .
H3 H 1.096(5) 0.435(5) 0.090(2) 0.086(11) Uiso 1 1 d . .
H4 H 0.636(4) 0.089(5) 0.034(2) 0.082(11) Uiso 1 1 d . .
H5 H 1.002(4) 0.607(4) 0.143(2) 0.077(11) Uiso 1 1 d . .
H6 H 0.532(4) 0.276(4) 0.086(2) 0.076(10) Uiso 1 1 d . .
H7 H 1.237(6) 0.628(5) 0.410(3) 0.112(14) Uiso 1 1 d . .
H8 H 0.832(6) 0.188(6) 0.392(3) 0.121(15) Uiso 1 1 d . .
H9 H 1.057(5) 0.735(5) 0.338(2) 0.087(12) Uiso 1 1 d . .
H10 H 0.662(6) 0.297(5) 0.314(3) 0.114(15) Uiso 1 1 d . .
B1 B 0.4958(5) 0.5708(6) 0.1327(2) 0.0719(11) Uani 1 1 d . .
B2 B 0.6789(6) 0.7461(5) 0.1267(2) 0.0727(11) Uani 1 1 d . .
B3 B 0.5088(7) 0.7711(7) 0.1643(3) 0.0935(16) Uani 1 1 d . .
B4 B 0.4196(6) 0.6062(7) 0.2231(3) 0.0858(14) Uani 1 1 d . .
B5 B 0.5349(5) 0.4809(6) 0.2233(2) 0.0654(10) Uani 1 1 d . .
B6 B 0.8297(5) 0.7628(5) 0.2133(2) 0.0637(10) Uani 1 1 d . .
B7 B 0.7160(7) 0.8900(6) 0.2132(3) 0.0827(13) Uani 1 1 d . .
B8 B 0.5540(7) 0.8044(7) 0.2723(3) 0.0890(15) Uani 1 1 d . .
B9 B 0.5703(5) 0.6253(6) 0.3093(2) 0.0731(12) Uani 1 1 d . .
B10 B 0.7526(6) 0.7995(5) 0.3032(2) 0.0702(11) Uani 1 1 d . .
H101 H 0.426(4) 0.476(4) 0.077(2) 0.073(9) Uiso 1 1 d . .
H102 H 0.485(4) 0.339(4) 0.2238(19) 0.073(9) Uiso 1 1 d . .
H103 H 0.286(5) 0.540(4) 0.225(2) 0.092(11) Uiso 1 1 d . .
H104 H 0.426(5) 0.819(5) 0.129(2) 0.104(12) Uiso 1 1 d . .
H105 H 0.715(4) 0.764(4) 0.069(2) 0.081(10) Uiso 1 1 d . .
H106 H 0.964(4) 0.798(3) 0.2084(17) 0.058(8) Uiso 1 1 d . .
H107 H 0.784(5) 1.023(6) 0.205(3) 0.127(15) Uiso 1 1 d . .
H108 H 0.517(4) 0.896(4) 0.317(2) 0.090(11) Uiso 1 1 d . .
H109 H 0.546(4) 0.581(4) 0.365(2) 0.076(9) Uiso 1 1 d . .
H110 H 0.834(4) 0.861(4) 0.359(2) 0.075(9) Uiso 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.jorganchem.2016.10.028 2016
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
C9 C1 B2 124.3(2) .
C9 C1 B1 122.1(3) .
B2 C1 B1 62.5(2) .
C9 C1 B6 119.0(2) .
B2 C1 B6 62.4(2) .
B1 C1 B6 113.1(3) .
C9 C1 C2 117.0(2) .
B2 C1 C2 109.8(2) .
B1 C1 C2 109.5(2) .
B6 C1 C2 60.16(18) .
C9 C1 B5 115.9(3) .
B2 C1 B5 112.8(3) .
B1 C1 B5 62.0(2) .
B6 C1 B5 111.3(2) .
C2 C1 B5 59.88(18) .
C3 C2 B10 121.0(3) .
C3 C2 B9 122.0(2) .
B10 C2 B9 62.4(2) .
C3 C2 C1 119.0(2) .
B10 C2 C1 109.7(2) .
B9 C2 C1 109.9(2) .
C3 C2 B6 117.3(3) .
B10 C2 B6 62.5(2) .
B9 C2 B6 113.1(3) .
C1 C2 B6 59.72(19) .
C3 C2 B5 118.9(3) .
B10 C2 B5 112.9(3) .
B9 C2 B5 62.1(2) .
C1 C2 B5 60.34(18) .
B6 C2 B5 111.3(2) .
C4 C3 C8 117.5(3) .
C4 C3 C2 121.9(3) .
C8 C3 C2 120.5(3) .
C3 C4 C5 120.5(4) .
C6 C5 C4 122.3(4) .
C7 C6 C5 116.8(4) .
C7 C6 C18 121.5(5) .
C5 C6 C18 121.5(5) .
C6 C7 C8 121.8(4) .
C7 C8 C3 121.0(4) .
C14 C9 C10 117.6(3) .
C14 C9 C1 120.3(3) .
C10 C9 C1 122.0(3) .
C11 C10 C9 121.1(3) .
C10 C11 C12 121.5(3) .
C11 C12 C13 117.2(3) .
C11 C12 C15 121.3(3) .
C13 C12 C15 121.5(3) .
C14 C13 C12 121.6(3) .
C13 C14 C9 120.9(3) .
C17 C15 C16 118.0(3) .
C17 C15 C12 121.6(3) .
C16 C15 C12 120.3(3) .
C17 C16 C15 120.8(3) 2_755
C16 C17 C15 121.2(3) 2_755
C6 C18 C19 112.4(4) .
C18 C19 C20 109.5(7) .
C21 C20 C19 94.3(11) .
C1 B1 B3 105.2(3) .
C1 B1 B2 58.5(2) .
B3 B1 B2 60.1(3) .
C1 B1 B4 105.8(3) .
B3 B1 B4 59.8(3) .
B2 B1 B4 108.0(3) .
C1 B1 B5 59.64(19) .
B3 B1 B5 107.0(3) .
B2 B1 B5 107.7(3) .
B4 B1 B5 59.3(2) .
C1 B2 B1 59.0(2) .
C1 B2 B3 105.4(3) .
B1 B2 B3 59.9(3) .
C1 B2 B7 105.7(3) .
B1 B2 B7 108.0(3) .
B3 B2 B7 59.9(3) .
C1 B2 B6 59.2(2) .
B1 B2 B6 107.7(3) .
B3 B2 B6 107.2(3) .
B7 B2 B6 59.5(2) .
B8 B3 B4 60.3(3) .
B8 B3 B7 60.5(3) .
B4 B3 B7 108.3(3) .
B8 B3 B1 108.8(3) .
B4 B3 B1 60.3(3) .
B7 B3 B1 108.2(3) .
B8 B3 B2 108.8(3) .
B4 B3 B2 108.3(3) .
B7 B3 B2 60.0(3) .
B1 B3 B2 60.0(2) .
B5 B4 B9 60.4(2) .
B5 B4 B3 107.9(3) .
B9 B4 B3 107.7(4) .
B5 B4 B8 108.2(3) .
B9 B4 B8 59.9(3) .
B3 B4 B8 59.6(3) .
B5 B4 B1 60.4(2) .
B9 B4 B1 108.8(3) .
B3 B4 B1 59.9(3) .
B8 B4 B1 108.1(4) .
C2 B5 C1 59.77(18) .
C2 B5 B4 105.4(3) .
C1 B5 B4 105.5(3) .
C2 B5 B9 58.3(2) .
C1 B5 B9 106.4(3) .
B4 B5 B9 59.9(2) .
C2 B5 B1 106.4(3) .
C1 B5 B1 58.3(2) .
B4 B5 B1 60.3(2) .
B9 B5 B1 108.3(3) .
C1 B6 C2 60.12(19) .
C1 B6 B7 105.6(3) .
C2 B6 B7 105.2(3) .
C1 B6 B2 58.4(2) .
C2 B6 B2 106.6(3) .
B7 B6 B2 60.2(2) .
C1 B6 B10 106.4(3) .
C2 B6 B10 58.0(2) .
B7 B6 B10 59.9(2) .
B2 B6 B10 108.2(3) .
B6 B7 B10 60.5(2) .
B6 B7 B3 107.9(3) .
B10 B7 B3 107.5(4) .
B6 B7 B2 60.2(2) .
B10 B7 B2 108.7(3) .
B3 B7 B2 60.1(3) .
B6 B7 B8 108.2(3) .
B10 B7 B8 59.8(3) .
B3 B7 B8 59.5(3) .
B2 B7 B8 108.1(4) .
B3 B8 B9 108.0(3) .
B3 B8 B10 107.9(3) .
B9 B8 B10 59.9(2) .
B3 B8 B4 60.1(3) .
B9 B8 B4 59.8(3) .
B10 B8 B4 107.7(3) .
B3 B8 B7 60.0(3) .
B9 B8 B7 107.7(3) .
B10 B8 B7 59.8(3) .
B4 B8 B7 107.8(3) .
C2 B9 B10 58.6(2) .
C2 B9 B8 105.8(3) .
B10 B9 B8 60.2(3) .
C2 B9 B4 106.1(3) .
B10 B9 B4 108.2(3) .
B8 B9 B4 60.3(3) .
C2 B9 B5 59.54(19) .
B10 B9 B5 107.7(3) .
B8 B9 B5 107.8(3) .
B4 B9 B5 59.6(2) .
C2 B10 B9 59.0(2) .
C2 B10 B7 106.1(3) .
B9 B10 B7 108.3(3) .
C2 B10 B8 105.9(3) .
B9 B10 B8 59.9(3) .
B7 B10 B8 60.4(3) .
C2 B10 B6 59.53(19) .
B9 B10 B6 108.0(3) .
B7 B10 B6 59.6(2) .
B8 B10 B6 107.9(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C9 1.503(4) .
C1 B2 1.711(5) .
C1 B1 1.718(5) .
C1 B6 1.725(5) .
C1 C2 1.732(4) .
C1 B5 1.742(5) .
C2 C3 1.503(4) .
C2 B10 1.705(5) .
C2 B9 1.712(5) .
C2 B6 1.733(5) .
C2 B5 1.734(5) .
C3 C4 1.380(5) .
C3 C8 1.392(5) .
C4 C5 1.386(5) .
C5 C6 1.380(6) .
C6 C7 1.376(6) .
C6 C18 1.503(5) .
C7 C8 1.382(5) .
C9 C14 1.382(4) .
C9 C10 1.394(4) .
C10 C11 1.373(4) .
C11 C12 1.380(4) .
C12 C13 1.394(4) .
C12 C15 1.484(4) .
C13 C14 1.375(4) .
C15 C17 1.390(4) .
C15 C16 1.401(4) .
C16 C17 1.384(4) 2_755
C17 C16 1.384(4) 2_755
C18 C19 1.507(8) .
C19 C20 1.602(10) .
C20 C21 1.485(15) .
B1 B3 1.776(7) .
B1 B2 1.778(7) .
B1 B4 1.782(5) .
B1 B5 1.784(5) .
B2 B3 1.780(6) .
B2 B7 1.779(6) .
B2 B6 1.780(6) .
B3 B8 1.766(6) .
B3 B4 1.774(8) .
B3 B7 1.777(8) .
B4 B5 1.764(6) .
B4 B9 1.770(6) .
B4 B8 1.777(8) .
B5 B9 1.779(6) .
B6 B7 1.767(5) .
B6 B10 1.783(5) .
B7 B10 1.773(6) .
B7 B8 1.785(7) .
B8 B9 1.770(7) .
B8 B10 1.775(6) .
B9 B10 1.770(7) .
