#------------------------------------------------------------------------------
#$Date: 2016-03-25 14:24:27 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179894 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/90/7019091.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_7019091
loop_
_publ_author_name
'Wang, Renjie'
'Deng, Lijun'
'Zhang, Ting'
'Li, Jiuyan'
_publ_section_title
;
 Substituent effect on the photophysical properties, electrochemical
 properties and electroluminescence performance of orange-emitting iridium
 complexes.
;
_journal_issue                   22
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6833
_journal_page_last               6841
_journal_paper_doi               10.1039/c2dt12206e
_journal_volume                  41
_journal_year                    2012
_chemical_formula_sum            'C33 H25 F6 Ir N2 O4 S2'
_chemical_formula_weight         883.87
_chemical_name_systematic
;
?
;
_space_group_IT_number           45
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.985(6)
_cell_length_b                   16.493(8)
_cell_length_c                   17.398(8)
_cell_measurement_reflns_used    3080
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.985
_cell_measurement_theta_min      3.156
_cell_volume                     3439(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7779
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    4.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.223
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.119
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(19)
_refine_ls_extinction_coef       0.00268(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2940
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0514P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0940
_reflns_number_gt                2278
_reflns_number_total             2940
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt12206e.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      Iba2
_cod_database_code               7019091
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ir1 Ir 1.5000 0.5000 0.97913(11) 0.04493(17) Uani 1 2 d S
S1 S 1.3284(2) 0.26520(12) 0.92665(13) 0.0659(6) Uani 1 1 d .
C4 C 1.5726(8) 0.4303(6) 0.8989(4) 0.054(2) Uani 1 1 d .
N1 N 1.3874(5) 0.4072(3) 0.9733(4) 0.0458(13) Uani 1 1 d .
C17 C 1.2435(7) 0.3152(4) 0.9933(4) 0.0533(19) Uani 1 1 d .
C10 C 1.4182(7) 0.3468(5) 0.9273(5) 0.0522(18) Uani 1 1 d .
C16 C 1.1436(8) 0.2885(5) 1.0254(5) 0.063(2) Uani 1 1 d .
H16A H 1.1154 0.2374 1.0140 0.076 Uiso 1 1 calc R
C11 C 1.2849(7) 0.3924(5) 1.0088(4) 0.0475(18) Uani 1 1 d .
F3 F 0.9540(5) 0.2388(4) 1.1010(4) 0.0863(16) Uani 1 1 d .
C12 C 1.2291(6) 0.4434(5) 1.0568(4) 0.0542(19) Uani 1 1 d .
H12A H 1.2569 0.4950 1.0665 0.065 Uiso 1 1 calc R
O1 O 1.4205(4) 0.5691(3) 1.0672(3) 0.0469(13) Uani 1 1 d .
C2 C 1.5000 0.5000 1.1731(8) 0.069(4) Uani 1 2 d S
H2A H 1.5000 0.5000 1.2265 0.083 Uiso 1 2 calc SR
C6 C 1.7086(8) 0.3917(7) 0.8023(5) 0.075(3) Uani 1 1 d .
H6A H 1.7724 0.4040 0.7743 0.089 Uiso 1 1 calc R
C9 C 1.5209(7) 0.3573(6) 0.8841(5) 0.056(2) Uani 1 1 d .
C5 C 1.6697(8) 0.4472(6) 0.8572(4) 0.061(2) Uani 1 1 d .
H5A H 1.7084 0.4953 0.8658 0.073 Uiso 1 1 calc R
C8 C 1.5612(10) 0.3014(6) 0.8292(6) 0.073(3) Uani 1 1 d .
H8A H 1.5237 0.2529 0.8209 0.087 Uiso 1 1 calc R
C7 C 1.6540(8) 0.3187(7) 0.7888(5) 0.074(3) Uani 1 1 d .
H7A H 1.6812 0.2824 0.7525 0.089 Uiso 1 1 calc R
C14 C 1.0880(8) 0.3396(6) 1.0742(5) 0.065(2) Uani 1 1 d .
C1 C 1.4327(7) 0.5585(5) 1.1393(4) 0.053(2) Uani 1 1 d .
C13 C 1.1308(7) 0.4182(5) 1.0914(5) 0.062(2) Uani 1 1 d .
H13A H 1.0933 0.4522 1.1254 0.074 Uiso 1 1 calc R
C3 C 1.3602(9) 0.6119(6) 1.1886(5) 0.072(3) Uani 1 1 d .
H3A H 1.3639 0.6667 1.1702 0.108 Uiso 1 1 calc R
H3B H 1.3859 0.6099 1.2408 0.108 Uiso 1 1 calc R
H3C H 1.2844 0.5931 1.1862 0.108 Uiso 1 1 calc R
F2 F 0.9809(7) 0.3293(8) 1.1865(5) 0.155(5) Uani 1 1 d .
O1W O 0.9428(6) 0.4243(3) 1.3547(4) 0.072(2) Uani 1 1 d .
F1 F 0.8967(6) 0.3626(5) 1.0843(6) 0.127(3) Uani 1 1 d .
C15 C 0.9796(10) 0.3186(9) 1.1120(8) 0.090(4) Uani 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Ir Ir -1.4442 7.9887 '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'
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
C4 Ir1 C4 91.8(5) . 2_865
C4 Ir1 N1 79.8(3) . .
C4 Ir1 N1 96.2(3) 2_865 .
C4 Ir1 N1 96.2(3) . 2_865
C4 Ir1 N1 79.8(3) 2_865 2_865
N1 Ir1 N1 174.3(4) . 2_865
C4 Ir1 O1 90.0(2) . 2_865
C4 Ir1 O1 177.3(4) 2_865 2_865
N1 Ir1 O1 86.0(2) . 2_865
N1 Ir1 O1 98.1(2) 2_865 2_865
C4 Ir1 O1 177.3(4) . .
C4 Ir1 O1 90.0(2) 2_865 .
N1 Ir1 O1 98.1(2) . .
N1 Ir1 O1 86.0(2) 2_865 .
O1 Ir1 O1 88.2(3) 2_865 .
C10 S1 C17 89.5(4) . .
C9 C4 C5 116.8(8) . .
C9 C4 Ir1 115.8(7) . .
C5 C4 Ir1 127.4(7) . .
C10 N1 C11 112.3(6) . .
C10 N1 Ir1 114.1(5) . .
C11 N1 Ir1 133.6(5) . .
C16 C17 C11 121.1(7) . .
C16 C17 S1 128.2(6) . .
C11 C17 S1 110.6(6) . .
N1 C10 C9 117.2(7) . .
N1 C10 S1 114.6(6) . .
C9 C10 S1 128.2(6) . .
C14 C16 C17 118.3(8) . .
C12 C11 C17 120.6(7) . .
C12 C11 N1 126.6(7) . .
C17 C11 N1 112.8(6) . .
C11 C12 C13 119.9(7) . .
C1 O1 Ir1 125.6(6) . .
C1 C2 C1 129.9(12) 2_865 .
C7 C6 C5 121.7(9) . .
C4 C9 C8 122.8(9) . .
C4 C9 C10 112.9(8) . .
C8 C9 C10 124.2(9) . .
C4 C5 C6 119.9(10) . .
C7 C8 C9 119.8(10) . .
C8 C7 C6 119.0(8) . .
C16 C14 C13 120.9(8) . .
C16 C14 C15 123.6(10) . .
C13 C14 C15 115.5(10) . .
O1 C1 C2 125.3(9) . .
O1 C1 C3 114.5(8) . .
C2 C1 C3 120.1(8) . .
C12 C13 C14 119.2(8) . .
F2 C15 F1 107.2(15) . .
F2 C15 F3 105.8(11) . .
F1 C15 F3 108.0(9) . .
F2 C15 C14 113.2(10) . .
F1 C15 C14 111.4(10) . .
F3 C15 C14 110.9(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C4 2.007(9) .
Ir1 C4 2.007(9) 2_865
Ir1 N1 2.043(5) .
Ir1 N1 2.043(5) 2_865
Ir1 O1 2.134(6) 2_865
Ir1 O1 2.134(6) .
S1 C10 1.723(8) .
S1 C17 1.748(8) .
C4 C9 1.379(13) .
C4 C5 1.400(12) .
N1 C10 1.331(9) .
N1 C11 1.396(10) .
C17 C16 1.393(12) .
C17 C11 1.394(9) .
C10 C9 1.453(12) .
C16 C14 1.369(14) .
C11 C12 1.360(11) .
F3 C15 1.365(16) .
C12 C13 1.386(11) .
O1 C1 1.275(9) .
C2 C1 1.388(10) 2_865
C2 C1 1.388(10) .
C6 C7 1.389(14) .
C6 C5 1.402(12) .
C9 C8 1.412(13) .
C8 C7 1.346(15) .
C14 C13 1.427(13) .
C14 C15 1.496(15) .
C1 C3 1.505(12) .
F2 C15 1.308(16) .
F1 C15 1.321(15) .
