#------------------------------------------------------------------------------
#$Date: 2019-11-24 16:45:01 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238626 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/78/7237811.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_7237811
loop_
_publ_author_name
'Lu, Guang-Zhao'
'Tu, Zhen-Long'
'Liu, Liang'
'Zhang, Wen-Wei'
'Zheng, You-Xuan'
_publ_section_title
;
 Fast synthesis of iridium(iii) complexes with sulfur-containing ancillary
 ligand for high-performance green OLEDs with EQE exceeding 31%
;
_journal_issue                   24
_journal_name_full               'Journal of Materials Chemistry C'
_journal_page_first              7273
_journal_paper_doi               10.1039/C9TC01397K
_journal_volume                  7
_journal_year                    2019
_chemical_formula_sum            'C31 H24 F12 Ir N5 S2'
_chemical_formula_weight         950.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-03-26 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.941(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.763(2)
_cell_length_b                   11.7754(14)
_cell_length_c                   17.580(2)
_cell_measurement_reflns_used    3116
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      23.89
_cell_measurement_theta_min      2.27
_cell_volume                     3568.8(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0677
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11771
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_min         2.094
_exptl_absorpt_coefficient_mu    3.951
_exptl_absorpt_correction_T_max  0.7186
_exptl_absorpt_correction_T_min  0.5264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         2.477
_refine_diff_density_min         -2.559
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4094
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0526P)²+12.1567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3427
_reflns_number_total             4094
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9tc01397k2.cif
_cod_data_source_block           20170924zyx_TN4Tlgz_0m_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7237811
_shelx_shelxl_version_number     2016/6
_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.
;
_shelx_estimated_absorpt_t_min   0.477
_shelx_estimated_absorpt_t_max   0.628
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5628(3) 0.2946(5) 0.3285(3) 0.0285(12) Uani 1 1 d . . . . .
C2 C 0.6234(3) 0.2197(6) 0.3283(3) 0.0335(14) Uani 1 1 d . . . . .
C3 C 0.6390(4) 0.1676(7) 0.4564(4) 0.0438(17) Uani 1 1 d . . . . .
C4 C 0.5789(4) 0.2355(7) 0.4646(3) 0.0446(17) Uani 1 1 d . . . . .
H4 H 0.564313 0.239417 0.513133 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5399(3) 0.2983(6) 0.4009(3) 0.0339(14) Uani 1 1 d . . . . .
C6 C 0.4725(3) 0.3672(6) 0.4043(4) 0.0358(14) Uani 1 1 d . . . . .
C7 C 0.4430(4) 0.3811(7) 0.4697(4) 0.0483(19) Uani 1 1 d . . . . .
H7 H 0.467485 0.344990 0.517564 0.058 Uiso 1 1 calc R U . . .
C8 C 0.3780(4) 0.4472(8) 0.4653(4) 0.054(2) Uani 1 1 d . . . . .
H8 H 0.357381 0.457204 0.509973 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3437(4) 0.4984(7) 0.3953(4) 0.0476(18) Uani 1 1 d . . . . .
H9 H 0.298609 0.543845 0.390742 0.057 Uiso 1 1 calc R U . . .
C10 C 0.3755(4) 0.4830(6) 0.3318(4) 0.0384(15) Uani 1 1 d . . . . .
H10 H 0.351511 0.518664 0.283547 0.046 Uiso 1 1 calc R U . . .
C11 C 0.6549(4) 0.1991(7) 0.2579(4) 0.0491(19) Uani 1 1 d . . . . .
C12 C 0.6839(5) 0.0961(9) 0.5242(5) 0.063(2) Uani 1 1 d . U . . .
C13 C 0.500000 0.6636(8) 0.250000 0.037(2) Uani 1 2 d S TU P . .
N3 N 0.500000 0.7755(9) 0.250000 0.079(3) Uani 1 2 d S TU P . .
C15 C 0.5559(6) 0.8383(9) 0.3107(8) 0.089(3) Uani 1 1 d . U . . .
H15 H 0.573855 0.767248 0.340793 0.107 Uiso 1 1 calc R U . . .
C16 C 0.6307(8) 0.8555(15) 0.2931(9) 0.142(6) Uani 1 1 d . U . . .
H16A H 0.652872 0.781867 0.284445 0.213 Uiso 1 1 calc R U . . .
H16B H 0.665543 0.894203 0.337234 0.213 Uiso 1 1 calc R U . . .
H16C H 0.624200 0.902195 0.245841 0.213 Uiso 1 1 calc R U . . .
C17 C 0.5284(10) 0.8839(17) 0.3727(8) 0.170(8) Uani 1 1 d . U . . .
H17A H 0.568817 0.877773 0.421507 0.256 Uiso 1 1 calc R U . . .
H17B H 0.482306 0.841815 0.377882 0.256 Uiso 1 1 calc R U . . .
H17C H 0.514897 0.963973 0.361937 0.256 Uiso 1 1 calc R U . . .
F1 F 0.5998(3) 0.1797(4) 0.1928(2) 0.0661(13) Uani 1 1 d . U . . .
F2 F 0.6951(3) 0.2880(5) 0.2422(3) 0.0762(15) Uani 1 1 d . U . . .
F3 F 0.7033(3) 0.1109(5) 0.2657(3) 0.0835(18) Uani 1 1 d . U . . .
F4 F 0.6661(13) -0.0051(16) 0.5224(12) 0.133(8) Uani 0.60(2) 1 d . U P A 1
F5 F 0.7599(8) 0.1038(16) 0.5314(8) 0.075(5) Uani 0.60(2) 1 d . U P A 1
F6 F 0.6793(7) 0.1461(17) 0.5940(5) 0.084(5) Uani 0.60(2) 1 d . U P A 1
Ir1 Ir 0.500000 0.41230(3) 0.250000 0.02574(12) Uani 1 2 d S T P . .
N1 N 0.6604(3) 0.1573(5) 0.3901(3) 0.0420(14) Uani 1 1 d . . . . .
N2 N 0.4387(3) 0.4200(4) 0.3356(3) 0.0307(11) Uani 1 1 d . . . . .
S1 S 0.56404(10) 0.57819(15) 0.31707(9) 0.0390(4) Uani 1 1 d . . . . .
F6' F 0.6427(14) 0.061(2) 0.5704(14) 0.092(8) Uani 0.40(2) 1 d . U P A 2
F5' F 0.7527(18) 0.130(3) 0.5533(18) 0.110(10) Uani 0.40(2) 1 d . U P A 2
F4' F 0.6979(12) -0.0151(19) 0.4956(10) 0.075(6) Uani 0.40(2) 1 d . U P A 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
_geom_angle_site_symmetry_3
C2 C1 C5 114.1(5) . .
C2 C1 Ir1 135.4(4) . .
C5 C1 Ir1 110.4(4) . .
N1 C2 C1 124.9(5) . .
N1 C2 C11 111.9(5) . .
C1 C2 C11 123.2(6) . .
N1 C3 C4 123.2(6) . .
N1 C3 C12 115.7(6) . .
C4 C3 C12 121.1(6) . .
C3 C4 C5 118.5(6) . .
C3 C4 H4 120.7 . .
C5 C4 H4 120.7 . .
C4 C5 C1 120.8(6) . .
C4 C5 C6 121.3(5) . .
C1 C5 C6 117.9(5) . .
N2 C6 C7 120.6(6) . .
N2 C6 C5 114.0(5) . .
C7 C6 C5 125.4(6) . .
C8 C7 C6 120.1(6) . .
C8 C7 H7 120.0 . .
C6 C7 H7 120.0 . .
C7 C8 C9 118.8(6) . .
C7 C8 H8 120.6 . .
C9 C8 H8 120.6 . .
C8 C9 C10 119.2(6) . .
C8 C9 H9 120.4 . .
C10 C9 H9 120.4 . .
N2 C10 C9 122.5(6) . .
N2 C10 H10 118.8 . .
C9 C10 H10 118.8 . .
F1 C11 F2 106.1(6) . .
F1 C11 F3 106.0(6) . .
F2 C11 F3 105.5(6) . .
F1 C11 C2 113.2(6) . .
F2 C11 C2 111.7(6) . .
F3 C11 C2 113.6(6) . .
F5' C12 F6' 119.0(18) . .
F4 C12 F5 108.5(15) . .
F4 C12 F6 111.4(13) . .
F5 C12 F6 99.3(10) . .
F5' C12 F4' 101.1(17) . .
F6' C12 F4' 95.5(16) . .
F4 C12 C3 115.6(10) . .
F5' C12 C3 114.7(16) . .
F6' C12 C3 113.8(10) . .
F5 C12 C3 111.6(9) . .
F6 C12 C3 109.2(9) . .
F4' C12 C3 109.3(10) . .
N3 C13 S1 125.2(3) . 2_655
N3 C13 S1 125.2(3) . .
S1 C13 S1 109.6(5) 2_655 .
C13 N3 C15 120.2(6) . .
C13 N3 C15 120.2(6) . 2_655
C15 N3 C15 119.6(12) . 2_655
C16 C15 N3 114.1(10) . .
C16 C15 C17 128.3(12) . .
N3 C15 C17 117.2(10) . .
C16 C15 H15 92.1 . .
N3 C15 H15 92.1 . .
C17 C15 H15 92.1 . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
H16A C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N2 Ir1 N2 175.0(3) . 2_655
N2 Ir1 C1 102.7(2) . 2_655
N2 Ir1 C1 80.7(2) 2_655 2_655
N2 Ir1 C1 80.7(2) . .
N2 Ir1 C1 102.7(2) 2_655 .
C1 Ir1 C1 96.5(3) 2_655 .
N2 Ir1 S1 82.98(15) . .
N2 Ir1 S1 92.93(15) 2_655 .
C1 Ir1 S1 167.19(16) 2_655 .
C1 Ir1 S1 95.76(17) . .
N2 Ir1 S1 92.93(15) . 2_655
N2 Ir1 S1 82.98(14) 2_655 2_655
C1 Ir1 S1 95.76(17) 2_655 2_655
C1 Ir1 S1 167.19(16) . 2_655
S1 Ir1 S1 72.31(8) . 2_655
C3 N1 C2 118.4(6) . .
C10 N2 C6 118.9(5) . .
C10 N2 Ir1 125.1(4) . .
C6 N2 Ir1 115.5(4) . .
C13 S1 Ir1 89.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.392(8) .
C1 C5 1.426(8) .
C1 Ir1 2.081(6) .
C2 N1 1.345(8) .
C2 C11 1.497(9) .
C3 N1 1.316(8) .
C3 C4 1.369(9) .
C3 C12 1.519(10) .
C4 C5 1.381(9) .
C4 H4 0.9500 .
C5 C6 1.460(8) .
C6 N2 1.363(8) .
C6 C7 1.382(9) .
C7 C8 1.379(10) .
C7 H7 0.9500 .
C8 C9 1.374(10) .
C8 H8 0.9500 .
C9 C10 1.380(9) .
C9 H9 0.9500 .
C10 N2 1.334(8) .
C10 H10 0.9500 .
C11 F1 1.334(9) .
C11 F2 1.332(9) .
C11 F3 1.335(8) .
C12 F4 1.232(17) .
C12 F5' 1.27(3) .
C12 F6' 1.288(18) .
C12 F5 1.328(18) .
C12 F6 1.381(14) .
C12 F4' 1.45(2) .
C13 N3 1.318(14) .
C13 S1 1.746(6) 2_655
C13 S1 1.746(6) .
N3 C15 1.470(11) .
N3 C15 1.470(11) 2_655
C15 C16 1.450(15) .
C15 C17 1.403(16) .
C15 H15 1.0000 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
Ir1 N2 2.060(5) .
Ir1 N2 2.060(5) 2_655
Ir1 S1 2.4195(17) .
Ir1 S1 2.4195(17) 2_655
