#------------------------------------------------------------------------------
#$Date: 2016-03-25 08:49:35 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179709 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/12/7001269.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_7001269
loop_
_publ_author_name
'Lee, Kyu Reon'
'Eum, Min-Sik'
'Chin, Chong Shik'
'Lee, Seung Chan'
'Kim, In June'
'Kim, Young Sik'
'Kim, Youngmee'
'Kim, Sung-Jin'
'Hur, Nam Hwi'
_publ_section_title
;
 New heteroleptic iridium complexes having one
 biphenyl-2,2′-diyl and two bipyridyl based ligands
;
_journal_issue                   19
_journal_name_full               'Dalton Transactions'
_journal_page_first              3650
_journal_page_last               3652
_journal_paper_doi               10.1039/b904016c
_journal_year                    2009
_chemical_formula_sum            'C37 H32 F3 Ir N4 O3 S'
_chemical_formula_weight         861.93
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 107.1220(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   34.693(2)
_cell_length_b                   11.2292(6)
_cell_length_c                   18.9912(11)
_cell_measurement_reflns_used    6142
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.02
_cell_measurement_theta_min      2.24
_cell_volume                     7070.6(7)
_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 0.969
_diffrn_measured_fraction_theta_max 0.969
_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  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0417
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16134
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    3.893
_exptl_absorpt_correction_T_max  0.459
_exptl_absorpt_correction_T_min  0.409
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS: Bruker, 1997)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             3408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.118
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5917
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0856P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1293
_reflns_number_gt                4437
_reflns_number_total             5917
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b904016c.txt
_cod_data_source_block           yk658sadc2c
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7001269
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.596659(7) 0.26521(2) 0.944743(12) 0.04032(13) Uani 1 1 d . . .
N11 N 0.62088(16) 0.3537(5) 1.0401(3) 0.0459(13) Uani 1 1 d . . .
N12 N 0.65708(17) 0.2892(5) 0.9442(3) 0.0483(14) Uani 1 1 d . . .
C11 C 0.6022(2) 0.3773(7) 1.0922(4) 0.0574(19) Uani 1 1 d . . .
H11 H 0.5757 0.3516 1.0833 0.069 Uiso 1 1 calc R . .
C12 C 0.6194(2) 0.4350(8) 1.1555(4) 0.071(2) Uani 1 1 d . . .
H12 H 0.6049 0.4480 1.1890 0.086 Uiso 1 1 calc R . .
C13 C 0.6584(3) 0.4748(8) 1.1706(4) 0.069(2) Uani 1 1 d . . .
C14 C 0.6787(2) 0.4535(7) 1.1199(4) 0.068(2) Uani 1 1 d . . .
H14 H 0.7051 0.4796 1.1289 0.082 Uiso 1 1 calc R . .
C15 C 0.65961(19) 0.3925(6) 1.0544(3) 0.0459(16) Uani 1 1 d . . .
C16 C 0.6785(2) 0.3637(7) 0.9981(3) 0.0519(18) Uani 1 1 d . . .
C17 C 0.7161(2) 0.4059(8) 0.9965(4) 0.065(2) Uani 1 1 d . . .
H17 H 0.7303 0.4579 1.0331 0.078 Uiso 1 1 calc R . .
C18 C 0.7328(2) 0.3723(8) 0.9418(5) 0.066(2) Uani 1 1 d . . .
C19 C 0.7113(2) 0.2878(9) 0.8903(5) 0.065(2) Uani 1 1 d . . .
H19 H 0.7223 0.2570 0.8550 0.078 Uiso 1 1 calc R . .
C110 C 0.6746(3) 0.2518(6) 0.8925(4) 0.056(2) Uani 1 1 d . . .
H110 H 0.6605 0.1985 0.8568 0.068 Uiso 1 1 calc R . .
C111 C 0.6793(3) 0.5437(12) 1.2408(5) 0.115(4) Uani 1 1 d . . .
H11A H 0.6883 0.4891 1.2813 0.172 Uiso 1 1 calc R . .
H11B H 0.6607 0.5995 1.2511 0.172 Uiso 1 1 calc R . .
H11C H 0.7021 0.5858 1.2343 0.172 Uiso 1 1 calc R . .
C112 C 0.7724(2) 0.4246(10) 0.9393(5) 0.093(3) Uani 1 1 d . . .
H11D H 0.7673 0.4932 0.9077 0.139 Uiso 1 1 calc R . .
H11E H 0.7870 0.3664 0.9205 0.139 Uiso 1 1 calc R . .
H11F H 0.7879 0.4477 0.9881 0.139 Uiso 1 1 calc R . .
N21 N 0.61059(15) 0.0912(5) 0.9873(3) 0.0463(13) Uani 1 1 d . . .
N22 N 0.57752(16) 0.1654(5) 0.8514(3) 0.0479(14) Uani 1 1 d . . .
C21 C 0.6282(2) 0.0602(7) 1.0590(4) 0.0541(18) Uani 1 1 d . . .
H21 H 0.6325 0.1182 1.0955 0.065 Uiso 1 1 calc R . .
C22 C 0.6400(2) -0.0578(8) 1.0786(4) 0.065(2) Uani 1 1 d . . .
H22 H 0.6512 -0.0776 1.1280 0.078 Uiso 1 1 calc R . .
C23 C 0.6353(2) -0.1418(7) 1.0272(5) 0.067(2) Uani 1 1 d . . .
C24 C 0.6161(2) -0.1124(7) 0.9540(4) 0.0583(19) Uani 1 1 d . . .
H24 H 0.6116 -0.1700 0.9172 0.070 Uiso 1 1 calc R . .
C25 C 0.60394(19) 0.0053(7) 0.9368(3) 0.0467(16) Uani 1 1 d . . .
C26 C 0.5845(2) 0.0456(6) 0.8597(4) 0.0473(16) Uani 1 1 d . . .
C27 C 0.5730(2) -0.0303(7) 0.7992(4) 0.062(2) Uani 1 1 d . . .
H27 H 0.5783 -0.1115 0.8055 0.074 Uiso 1 1 calc R . .
C28 C 0.5541(2) 0.0137(8) 0.7307(4) 0.068(2) Uani 1 1 d . . .
C29 C 0.5469(2) 0.1343(8) 0.7232(4) 0.068(2) Uani 1 1 d . . .
H29 H 0.5337 0.1664 0.6773 0.081 Uiso 1 1 calc R . .
C210 C 0.5593(3) 0.2070(7) 0.7840(4) 0.063(2) Uani 1 1 d . . .
H210 H 0.5548 0.2885 0.7779 0.076 Uiso 1 1 calc R . .
C211 C 0.6498(3) -0.2690(9) 1.0444(8) 0.106(4) Uani 1 1 d . . .
H21A H 0.6783 -0.2729 1.0509 0.159 Uiso 1 1 calc R . .
H21B H 0.6359 -0.3199 1.0043 0.159 Uiso 1 1 calc R . .
H21C H 0.6444 -0.2947 1.0887 0.159 Uiso 1 1 calc R . .
C212 C 0.5412(3) -0.0698(10) 0.6648(5) 0.116(4) Uani 1 1 d . . .
H21D H 0.5638 -0.0850 0.6465 0.174 Uiso 1 1 calc R . .
H21E H 0.5199 -0.0337 0.6267 0.174 Uiso 1 1 calc R . .
H21F H 0.5319 -0.1436 0.6795 0.174 Uiso 1 1 calc R . .
C31 C 0.5794(2) 0.4261(6) 0.8945(3) 0.0462(16) Uani 1 1 d . . .
C32 C 0.6014(2) 0.5033(7) 0.8673(4) 0.059(2) Uani 1 1 d . . .
H32 H 0.6279 0.4837 0.8710 0.070 Uiso 1 1 calc R . .
C33 C 0.5859(3) 0.6113(7) 0.8338(4) 0.064(2) Uani 1 1 d . . .
H33 H 0.6015 0.6620 0.8146 0.077 Uiso 1 1 calc R . .
C34 C 0.5465(3) 0.6401(8) 0.8303(5) 0.075(2) Uani 1 1 d . . .
H34 H 0.5356 0.7113 0.8083 0.090 Uiso 1 1 calc R . .
C35 C 0.5230(3) 0.5664(8) 0.8585(5) 0.081(3) Uani 1 1 d . . .
H35 H 0.4968 0.5885 0.8561 0.097 Uiso 1 1 calc R . .
C36 C 0.5388(2) 0.4575(7) 0.8909(4) 0.059(2) Uani 1 1 d . . .
C37 C 0.5173(2) 0.3730(7) 0.9222(4) 0.0533(18) Uani 1 1 d . . .
C38 C 0.4786(2) 0.3845(9) 0.9275(6) 0.089(3) Uani 1 1 d . . .
H38 H 0.4640 0.4529 0.9088 0.107 Uiso 1 1 calc R . .
C39 C 0.4610(3) 0.3008(12) 0.9588(7) 0.099(4) Uani 1 1 d . . .
H39 H 0.4355 0.3146 0.9638 0.118 Uiso 1 1 calc R . .
C310 C 0.4807(3) 0.1942(9) 0.9835(5) 0.073(2) Uani 1 1 d . . .
H310 H 0.4680 0.1335 1.0017 0.088 Uiso 1 1 calc R . .
C311 C 0.5195(2) 0.1816(8) 0.9801(4) 0.061(2) Uani 1 1 d . . .
H311 H 0.5334 0.1119 0.9984 0.073 Uiso 1 1 calc R . .
C312 C 0.5389(2) 0.2667(6) 0.9510(4) 0.0480(18) Uani 1 1 d . . .
C1 C 0.7084(5) 0.8191(10) 0.8734(4) 0.40(2) Uiso 1 1 d D . .
F1 F 0.7488(4) 0.8058(17) 0.9002(10) 0.368(10) Uiso 1 1 d D . .
F2 F 0.6909(5) 0.7106(13) 0.8653(10) 0.315(8) Uiso 1 1 d D . .
F3 F 0.6951(7) 0.8836(15) 0.9215(5) 0.555(16) Uiso 1 1 d D . .
S1 S 0.69074(18) 0.9004(6) 0.7882(3) 0.214(2) Uiso 1 1 d D . .
O1 O 0.7061(6) 0.8141(14) 0.7477(13) 0.452(17) Uiso 1 1 d D . .
O2 O 0.64766(19) 0.9053(19) 0.7676(11) 0.462(15) Uiso 1 1 d D . .
O3 O 0.7097(5) 1.0145(9) 0.7928(10) 0.388(12) Uiso 1 1 d 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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
N11 Ir1 N22 174.0(2) . . ?
N11 Ir1 C312 95.8(3) . . ?
N22 Ir1 C312 88.9(3) . . ?
N11 Ir1 C31 88.3(2) . . ?
N22 Ir1 C31 96.0(2) . . ?
C312 Ir1 C31 82.1(3) . . ?
N11 Ir1 N21 97.1(2) . . ?
N22 Ir1 N21 78.6(2) . . ?
C312 Ir1 N21 95.9(3) . . ?
C31 Ir1 N21 174.4(2) . . ?
N11 Ir1 N12 77.9(2) . . ?
N22 Ir1 N12 97.8(2) . . ?
C312 Ir1 N12 171.7(3) . . ?
C31 Ir1 N12 92.3(3) . . ?
N21 Ir1 N12 90.2(2) . . ?
C11 N11 C15 116.5(6) . . ?
C11 N11 Ir1 126.0(5) . . ?
C15 N11 Ir1 117.6(4) . . ?
C16 N12 C110 117.9(7) . . ?
C16 N12 Ir1 113.5(5) . . ?
C110 N12 Ir1 128.1(5) . . ?
C12 C11 N11 124.6(7) . . ?
C12 C11 H11 117.7 . . ?
N11 C11 H11 117.7 . . ?
C11 C12 C13 119.5(8) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 118.4(7) . . ?
C14 C13 C111 119.4(8) . . ?
C12 C13 C111 122.1(8) . . ?
C13 C14 C15 120.1(7) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
N11 C15 C14 120.9(7) . . ?
N11 C15 C16 114.6(5) . . ?
C14 C15 C16 124.5(7) . . ?
N12 C16 C17 120.0(7) . . ?
N12 C16 C15 115.2(6) . . ?
C17 C16 C15 124.8(7) . . ?
C18 C17 C16 121.6(8) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 116.9(7) . . ?
C17 C18 C112 120.2(9) . . ?
C19 C18 C112 122.9(8) . . ?
C110 C19 C18 119.5(8) . . ?
C110 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C110 N12 123.8(8) . . ?
C19 C110 H110 118.1 . . ?
N12 C110 H110 118.1 . . ?
C13 C111 H11A 109.5 . . ?
C13 C111 H11B 109.5 . . ?
H11A C111 H11B 109.5 . . ?
C13 C111 H11C 109.5 . . ?
H11A C111 H11C 109.5 . . ?
H11B C111 H11C 109.5 . . ?
C18 C112 H11D 109.5 . . ?
C18 C112 H11E 109.5 . . ?
H11D C112 H11E 109.5 . . ?
C18 C112 H11F 109.5 . . ?
H11D C112 H11F 109.5 . . ?
H11E C112 H11F 109.5 . . ?
C25 N21 C21 117.8(6) . . ?
C25 N21 Ir1 115.0(4) . . ?
C21 N21 Ir1 127.0(5) . . ?
C210 N22 C26 118.1(6) . . ?
C210 N22 Ir1 125.7(5) . . ?
C26 N22 Ir1 116.1(4) . . ?
N21 C21 C22 121.0(7) . . ?
N21 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 120.7(7) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 118.9(7) . . ?
C22 C23 C211 123.2(9) . . ?
C24 C23 C211 117.9(9) . . ?
C23 C24 C25 118.7(7) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 H24 120.7 . . ?
N21 C25 C24 122.8(6) . . ?
N21 C25 C26 114.8(6) . . ?
C24 C25 C26 122.3(7) . . ?
N22 C26 C27 120.7(6) . . ?
N22 C26 C25 115.1(6) . . ?
C27 C26 C25 124.2(7) . . ?
C28 C27 C26 120.4(7) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 118.4(7) . . ?
C27 C28 C212 120.2(8) . . ?
C29 C28 C212 121.3(8) . . ?
C210 C29 C28 119.6(7) . . ?
C210 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
N22 C210 C29 122.8(7) . . ?
N22 C210 H210 118.6 . . ?
C29 C210 H210 118.6 . . ?
C23 C211 H21A 109.5 . . ?
C23 C211 H21B 109.5 . . ?
H21A C211 H21B 109.5 . . ?
C23 C211 H21C 109.5 . . ?
H21A C211 H21C 109.5 . . ?
H21B C211 H21C 109.5 . . ?
C28 C212 H21D 109.5 . . ?
C28 C212 H21E 109.5 . . ?
H21D C212 H21E 109.5 . . ?
C28 C212 H21F 109.5 . . ?
H21D C212 H21F 109.5 . . ?
H21E C212 H21F 109.5 . . ?
C32 C31 C36 118.7(6) . . ?
C32 C31 Ir1 128.5(5) . . ?
C36 C31 Ir1 112.8(5) . . ?
C31 C32 C33 123.0(8) . . ?
C31 C32 H32 118.5 . . ?
C33 C32 H32 118.5 . . ?
C34 C33 C32 117.6(8) . . ?
C34 C33 H33 121.2 . . ?
C32 C33 H33 121.2 . . ?
C35 C34 C33 122.0(8) . . ?
C35 C34 H34 119.0 . . ?
C33 C34 H34 119.0 . . ?
C34 C35 C36 119.6(8) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C35 C36 C31 119.1(8) . . ?
C35 C36 C37 124.8(8) . . ?
C31 C36 C37 116.1(6) . . ?
C38 C37 C312 117.5(8) . . ?
C38 C37 C36 127.0(7) . . ?
C312 C37 C36 115.5(6) . . ?
C39 C38 C37 122.8(9) . . ?
C39 C38 H38 118.6 . . ?
C37 C38 H38 118.6 . . ?
C38 C39 C310 120.6(9) . . ?
C38 C39 H39 119.7 . . ?
C310 C39 H39 119.7 . . ?
C311 C310 C39 117.6(10) . . ?
C311 C310 H310 121.2 . . ?
C39 C310 H310 121.2 . . ?
C312 C311 C310 123.3(8) . . ?
C312 C311 H311 118.3 . . ?
C310 C311 H311 118.3 . . ?
C311 C312 C37 118.1(7) . . ?
C311 C312 Ir1 128.5(6) . . ?
C37 C312 Ir1 113.5(5) . . ?
F3 C1 F2 109.3(16) . . ?
F3 C1 F1 109.1(13) . . ?
F2 C1 F1 109.0(14) . . ?
F3 C1 S1 104.0(10) . . ?
F2 C1 S1 109.0(14) . . ?
F1 C1 S1 115.9(11) . . ?
O2 S1 O3 114.0(12) . . ?
O2 S1 O1 113.8(13) . . ?
O3 S1 O1 113.7(11) . . ?
O2 S1 C1 108.5(11) . . ?
O3 S1 C1 111.7(10) . . ?
O1 S1 C1 93.3(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N11 2.018(5) . ?
Ir1 N22 2.035(5) . ?
Ir1 C312 2.040(8) . ?
Ir1 C31 2.048(7) . ?
Ir1 N21 2.115(6) . ?
Ir1 N12 2.116(6) . ?
N11 C11 1.359(8) . ?
N11 C15 1.362(8) . ?
N12 C16 1.362(9) . ?
N12 C110 1.365(10) . ?
C11 C12 1.342(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.374(11) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(11) . ?
C13 C111 1.529(10) . ?
C14 C15 1.403(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.447(9) . ?
C16 C17 1.396(9) . ?
C17 C18 1.382(11) . ?
C17 H17 0.9300 . ?
C18 C19 1.409(13) . ?
C18 C112 1.506(10) . ?
C19 C110 1.346(12) . ?
C19 H19 0.9300 . ?
C110 H110 0.9300 . ?
C111 H11A 0.9600 . ?
C111 H11B 0.9600 . ?
C111 H11C 0.9600 . ?
C112 H11D 0.9600 . ?
C112 H11E 0.9600 . ?
C112 H11F 0.9600 . ?
N21 C25 1.331(8) . ?
N21 C21 1.364(8) . ?
N22 C210 1.334(9) . ?
N22 C26 1.369(9) . ?
C21 C22 1.405(11) . ?
C21 H21 0.9300 . ?
C22 C23 1.332(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.394(10) . ?
C23 C211 1.517(11) . ?
C24 C25 1.396(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.491(9) . ?
C26 C27 1.391(9) . ?
C27 C28 1.366(10) . ?
C27 H27 0.9300 . ?
C28 C29 1.377(12) . ?
C28 C212 1.522(10) . ?
C29 C210 1.377(10) . ?
C29 H29 0.9300 . ?
C210 H210 0.9300 . ?
C211 H21A 0.9600 . ?
C211 H21B 0.9600 . ?
C211 H21C 0.9600 . ?
C212 H21D 0.9600 . ?
C212 H21E 0.9600 . ?
C212 H21F 0.9600 . ?
C31 C32 1.353(10) . ?
C31 C36 1.434(9) . ?
C32 C33 1.402(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.386(11) . ?
C33 H33 0.9300 . ?
C34 C35 1.376(12) . ?
C34 H34 0.9300 . ?
C35 C36 1.406(11) . ?
C35 H35 0.9300 . ?
C36 C37 1.438(10) . ?
C37 C38 1.383(10) . ?
C37 C312 1.430(10) . ?
C38 C39 1.349(14) . ?
C38 H38 0.9300 . ?
C39 C310 1.390(16) . ?
C39 H39 0.9300 . ?
C310 C311 1.377(11) . ?
C310 H310 0.9300 . ?
C311 C312 1.376(11) . ?
C311 H311 0.9300 . ?
C1 F3 1.35(2) . ?
C1 F2 1.35(2) . ?
C1 F1 1.35(2) . ?
C1 S1 1.801(10) . ?
S1 O2 1.430(12) . ?
S1 O3 1.431(14) . ?
S1 O1 1.43(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C312 Ir1 N11 C11 11.5(6) . . . . ?
C31 Ir1 N11 C11 93.4(6) . . . . ?
N21 Ir1 N11 C11 -85.2(6) . . . . ?
N12 Ir1 N11 C11 -173.9(6) . . . . ?
C312 Ir1 N11 C15 -169.3(5) . . . . ?
C31 Ir1 N11 C15 -87.4(5) . . . . ?
N21 Ir1 N11 C15 93.9(5) . . . . ?
N12 Ir1 N11 C15 5.3(5) . . . . ?
N11 Ir1 N12 C16 -9.6(5) . . . . ?
N22 Ir1 N12 C16 174.5(5) . . . . ?
C312 Ir1 N12 C16 31.1(18) . . . . ?
C31 Ir1 N12 C16 78.2(5) . . . . ?
N21 Ir1 N12 C16 -106.9(5) . . . . ?
N11 Ir1 N12 C110 179.1(6) . . . . ?
N22 Ir1 N12 C110 3.3(6) . . . . ?
C31 Ir1 N12 C110 -93.1(6) . . . . ?
N21 Ir1 N12 C110 81.8(6) . . . . ?
C15 N11 C11 C12 -0.1(11) . . . . ?
Ir1 N11 C11 C12 179.1(6) . . . . ?
N11 C11 C12 C13 0.2(13) . . . . ?
C11 C12 C13 C14 -0.2(13) . . . . ?
C11 C12 C13 C111 178.5(9) . . . . ?
C12 C13 C14 C15 0.0(12) . . . . ?
C111 C13 C14 C15 -178.7(8) . . . . ?
C11 N11 C15 C14 -0.1(10) . . . . ?
Ir1 N11 C15 C14 -179.3(5) . . . . ?
C11 N11 C15 C16 179.0(6) . . . . ?
Ir1 N11 C15 C16 -0.3(8) . . . . ?
C13 C14 C15 N11 0.1(11) . . . . ?
C13 C14 C15 C16 -178.8(7) . . . . ?
C110 N12 C16 C17 4.3(10) . . . . ?
Ir1 N12 C16 C17 -167.9(5) . . . . ?
C110 N12 C16 C15 -175.3(6) . . . . ?
Ir1 N12 C16 C15 12.4(7) . . . . ?
N11 C15 C16 N12 -8.3(9) . . . . ?
C14 C15 C16 N12 170.7(7) . . . . ?
N11 C15 C16 C17 172.1(6) . . . . ?
C14 C15 C16 C17 -8.9(11) . . . . ?
N12 C16 C17 C18 -1.2(11) . . . . ?
C15 C16 C17 C18 178.4(7) . . . . ?
C16 C17 C18 C19 -3.8(11) . . . . ?
C16 C17 C18 C112 176.7(7) . . . . ?
C17 C18 C19 C110 5.6(11) . . . . ?
C112 C18 C19 C110 -174.9(7) . . . . ?
C18 C19 C110 N12 -2.6(11) . . . . ?
C16 N12 C110 C19 -2.4(10) . . . . ?
Ir1 N12 C110 C19 168.5(6) . . . . ?
N11 Ir1 N21 C25 -170.9(4) . . . . ?
N22 Ir1 N21 C25 4.8(4) . . . . ?
C312 Ir1 N21 C25 92.5(5) . . . . ?
C31 Ir1 N21 C25 23(3) . . . . ?
N12 Ir1 N21 C25 -93.1(5) . . . . ?
N11 Ir1 N21 C21 3.7(5) . . . . ?
N22 Ir1 N21 C21 179.4(6) . . . . ?
C312 Ir1 N21 C21 -92.9(6) . . . . ?
C31 Ir1 N21 C21 -162(2) . . . . ?
N12 Ir1 N21 C21 81.5(5) . . . . ?
N11 Ir1 N22 C210 -138(2) . . . . ?
C312 Ir1 N22 C210 80.7(7) . . . . ?
C31 Ir1 N22 C210 -1.3(7) . . . . ?
N21 Ir1 N22 C210 177.0(7) . . . . ?
N12 Ir1 N22 C210 -94.4(7) . . . . ?
C312 Ir1 N22 C26 -99.8(5) . . . . ?
C31 Ir1 N22 C26 178.2(5) . . . . ?
N21 Ir1 N22 C26 -3.6(5) . . . . ?
N12 Ir1 N22 C26 85.1(5) . . . . ?
C25 N21 C21 C22 1.9(10) . . . . ?
Ir1 N21 C21 C22 -172.6(5) . . . . ?
N21 C21 C22 C23 2.0(12) . . . . ?
C21 C22 C23 C24 -4.1(12) . . . . ?
C21 C22 C23 C211 176.0(8) . . . . ?
C22 C23 C24 C25 2.4(12) . . . . ?
C211 C23 C24 C25 -177.7(8) . . . . ?
C21 N21 C25 C24 -3.6(10) . . . . ?
Ir1 N21 C25 C24 171.6(6) . . . . ?
C21 N21 C25 C26 179.8(6) . . . . ?
Ir1 N21 C25 C26 -5.1(7) . . . . ?
C23 C24 C25 N21 1.5(11) . . . . ?
C23 C24 C25 C26 177.9(7) . . . . ?
C210 N22 C26 C27 0.3(11) . . . . ?
Ir1 N22 C26 C27 -179.2(5) . . . . ?
C210 N22 C26 C25 -178.4(7) . . . . ?
Ir1 N22 C26 C25 2.0(8) . . . . ?
N21 C25 C26 N22 2.1(9) . . . . ?
C24 C25 C26 N22 -174.6(7) . . . . ?
N21 C25 C26 C27 -176.6(7) . . . . ?
C24 C25 C26 C27 6.7(11) . . . . ?
N22 C26 C27 C28 -0.9(11) . . . . ?
C25 C26 C27 C28 177.8(7) . . . . ?
C26 C27 C28 C29 0.2(12) . . . . ?
C26 C27 C28 C212 -179.3(8) . . . . ?
C27 C28 C29 C210 1.0(13) . . . . ?
C212 C28 C29 C210 -179.5(8) . . . . ?
C26 N22 C210 C29 0.9(12) . . . . ?
Ir1 N22 C210 C29 -179.6(6) . . . . ?
C28 C29 C210 N22 -1.6(14) . . . . ?
N11 Ir1 C31 C32 83.6(6) . . . . ?
N22 Ir1 C31 C32 -92.3(6) . . . . ?
C312 Ir1 C31 C32 179.7(7) . . . . ?
N21 Ir1 C31 C32 -110(2) . . . . ?
N12 Ir1 C31 C32 5.8(6) . . . . ?
N11 Ir1 C31 C36 -94.8(5) . . . . ?
N22 Ir1 C31 C36 89.3(5) . . . . ?
C312 Ir1 C31 C36 1.3(5) . . . . ?
N12 Ir1 C31 C36 -172.6(5) . . . . ?
C36 C31 C32 C33 -1.8(10) . . . . ?
Ir1 C31 C32 C33 179.9(5) . . . . ?
C31 C32 C33 C34 1.4(11) . . . . ?
C32 C33 C34 C35 0.1(12) . . . . ?
C33 C34 C35 C36 -1.0(13) . . . . ?
C34 C35 C36 C31 0.6(12) . . . . ?
C34 C35 C36 C37 -179.9(7) . . . . ?
C32 C31 C36 C35 0.8(10) . . . . ?
Ir1 C31 C36 C35 179.4(6) . . . . ?
C32 C31 C36 C37 -178.7(6) . . . . ?
Ir1 C31 C36 C37 -0.2(8) . . . . ?
C35 C36 C37 C38 -1.7(13) . . . . ?
C31 C36 C37 C38 177.8(8) . . . . ?
C35 C36 C37 C312 178.8(7) . . . . ?
C31 C36 C37 C312 -1.7(9) . . . . ?
C312 C37 C38 C39 0.4(14) . . . . ?
C36 C37 C38 C39 -179.1(9) . . . . ?
C37 C38 C39 C310 -3.8(18) . . . . ?
C38 C39 C310 C311 4.9(16) . . . . ?
C39 C310 C311 C312 -2.6(13) . . . . ?
C310 C311 C312 C37 -0.7(11) . . . . ?
C310 C311 C312 Ir1 177.7(6) . . . . ?
C38 C37 C312 C311 1.8(11) . . . . ?
C36 C37 C312 C311 -178.6(7) . . . . ?
C38 C37 C312 Ir1 -176.8(6) . . . . ?
C36 C37 C312 Ir1 2.8(8) . . . . ?
N11 Ir1 C312 C311 -93.1(7) . . . . ?
N22 Ir1 C312 C311 83.2(7) . . . . ?
C31 Ir1 C312 C311 179.4(7) . . . . ?
N21 Ir1 C312 C311 4.7(7) . . . . ?
N11 Ir1 C312 C37 85.3(5) . . . . ?
N22 Ir1 C312 C37 -98.4(5) . . . . ?
C31 Ir1 C312 C37 -2.2(5) . . . . ?
N21 Ir1 C312 C37 -176.9(5) . . . . ?
F3 C1 S1 O2 -60.6(12) . . . . ?
F2 C1 S1 O2 55.9(12) . . . . ?
F1 C1 S1 O2 179.6(12) . . . . ?
F3 C1 S1 O3 65.9(12) . . . . ?
F2 C1 S1 O3 -177.5(11) . . . . ?
F1 C1 S1 O3 -53.9(12) . . . . ?
F3 C1 S1 O1 -177.0(11) . . . . ?
F2 C1 S1 O1 -60.5(11) . . . . ?
F1 C1 S1 O1 63.2(11) . . . . ?
