#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:53:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178728 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/39/4083979.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_4083979
loop_
_publ_author_name
'Prakash, Om'
'Joshi, Hemant'
'Sharma, Kamal Nayan'
'Gupta, Pancham Lal'
'Singh, Ajai K.'
_publ_section_title
;
 Transfer Hydrogenation (pH Independent) of Ketones and Aldehydes in Water
 with Glycerol: Ru, Rh, and Ir Catalysts with a COOH Group near the Metal
 on a (Phenylthio)methyl-2-pyridine Scaffold
;
_journal_issue                   14
_journal_name_full               Organometallics
_journal_page_first              3804
_journal_paper_doi               10.1021/om500515z
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C23 H26 Cl Ir N O2 S, F6 P, C H4 O'
_chemical_formula_sum            'C24 H30 Cl F6 Ir N O3 P S'
_chemical_formula_weight         785.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.759(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.512(3)
_cell_length_b                   13.441(3)
_cell_length_c                   14.886(3)
_cell_measurement_reflns_used    5111
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.25
_cell_volume                     2903.3(11)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            27243
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    4.883
_exptl_absorpt_correction_T_max  0.617
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.796
_exptl_crystal_density_meas      1.796
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.027
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         5111
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0520P)²+1.7194P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                4109
_reflns_number_total             5111
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om500515z_si_002.cif
_cod_data_source_block           complex3
_cod_depositor_comments
'Adding full bibliography for 4083977--4083980.cif.'
_cod_original_cell_volume        2903.4(11)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4083979
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
C1 C 0.5572(4) 0.1693(4) 0.9463(4) 0.0566(14) Uani 1 1 d .
C2 C 0.4970(4) 0.2456(5) 0.9269(4) 0.0646(15) Uani 1 1 d .
H2A H 0.4519 0.2364 0.8827 0.078 Uiso 1 1 calc R
C3 C 0.5018(5) 0.3351(5) 0.9713(5) 0.0748(18) Uani 1 1 d .
H3 H 0.4591 0.3848 0.9582 0.090 Uiso 1 1 calc R
C4 C 0.5697(6) 0.3515(6) 1.0353(5) 0.086(2) Uani 1 1 d .
H4 H 0.5731 0.4118 1.0657 0.103 Uiso 1 1 calc R
C5 C 0.6317(5) 0.2776(6) 1.0530(5) 0.0782(19) Uani 1 1 d .
H5 H 0.6785 0.2892 1.0950 0.094 Uiso 1 1 calc R
C6 C 0.6275(4) 0.1858(5) 1.0105(4) 0.0612(15) Uani 1 1 d .
C7 C 0.6935(5) 0.1075(6) 1.0374(4) 0.0719(17) Uani 1 1 d .
C8 C 0.4516(4) 0.0663(5) 0.8144(4) 0.0691(17) Uani 1 1 d .
H8A H 0.4267 0.0018 0.7976 0.083 Uiso 1 1 calc R
H8B H 0.4030 0.1036 0.8432 0.083 Uiso 1 1 calc R
C9 C 0.4796(4) 0.1198(4) 0.7319(4) 0.0599(15) Uani 1 1 d .
C10 C 0.4209(5) 0.1795(5) 0.6809(5) 0.080(2) Uani 1 1 d .
H10 H 0.3612 0.1915 0.7001 0.096 Uiso 1 1 calc R
C11 C 0.4505(6) 0.2208(6) 0.6026(5) 0.092(2) Uani 1 1 d .
H11 H 0.4108 0.2590 0.5672 0.110 Uiso 1 1 calc R
C12 C 0.5392(6) 0.2051(5) 0.5770(5) 0.088(2) Uani 1 1 d .
H12 H 0.5610 0.2323 0.5238 0.105 Uiso 1 1 calc R
C13 C 0.5954(5) 0.1489(5) 0.6306(4) 0.0730(18) Uani 1 1 d .
H13 H 0.6564 0.1403 0.6138 0.088 Uiso 1 1 calc R
C14 C 0.7725(4) -0.0512(5) 0.7151(4) 0.0632(15) Uani 1 1 d .
C15 C 0.6891(5) -0.0912(5) 0.6806(4) 0.0703(17) Uani 1 1 d .
C16 C 0.6397(4) -0.1354(4) 0.7531(5) 0.0689(17) Uani 1 1 d .
C17 C 0.6971(5) -0.1296(4) 0.8315(4) 0.0647(16) Uani 1 1 d .
C18 C 0.7775(4) -0.0755(4) 0.8098(4) 0.0636(16) Uani 1 1 d .
C19 C 0.8576(5) -0.0488(6) 0.8709(6) 0.099(3) Uani 1 1 d .
H19A H 0.8459 -0.0726 0.9304 0.149 Uiso 1 1 calc R
H19B H 0.8650 0.0221 0.8722 0.149 Uiso 1 1 calc R
H19C H 0.9128 -0.0791 0.8488 0.149 Uiso 1 1 calc R
C20 C 0.8474(6) 0.0009(6) 0.6656(7) 0.105(3) Uani 1 1 d .
H20A H 0.8993 -0.0429 0.6598 0.157 Uiso 1 1 calc R
H20B H 0.8658 0.0593 0.6981 0.157 Uiso 1 1 calc R
H20C H 0.8252 0.0196 0.6069 0.157 Uiso 1 1 calc R
C21 C 0.6574(7) -0.0905(7) 0.5835(5) 0.112(3) Uani 1 1 d .
H21A H 0.6895 -0.0394 0.5516 0.168 Uiso 1 1 calc R
H21B H 0.5923 -0.0778 0.5804 0.168 Uiso 1 1 calc R
H21C H 0.6701 -0.1540 0.5567 0.168 Uiso 1 1 calc R
C22 C 0.5516(5) -0.1954(6) 0.7451(7) 0.123(3) Uani 1 1 d .
H22A H 0.5664 -0.2648 0.7412 0.184 Uiso 1 1 calc R
H22B H 0.5181 -0.1754 0.6921 0.184 Uiso 1 1 calc R
H22C H 0.5145 -0.1839 0.7970 0.184 Uiso 1 1 calc R
C23 C 0.6750(6) -0.1761(6) 0.9206(5) 0.106(3) Uani 1 1 d .
H23A H 0.7140 -0.1480 0.9665 0.159 Uiso 1 1 calc R
H23B H 0.6851 -0.2466 0.9175 0.159 Uiso 1 1 calc R
H23C H 0.6116 -0.1635 0.9345 0.159 Uiso 1 1 calc R
C24 C 0.8788(10) -0.0765(8) 1.1561(10) 0.179(6) Uani 1 1 d .
H24A H 0.9312 -0.1012 1.1243 0.269 Uiso 1 1 calc R
H24B H 0.8233 -0.0958 1.1250 0.269 Uiso 1 1 calc R
H24C H 0.8788 -0.1037 1.2158 0.269 Uiso 1 1 calc R
N1 N 0.5672(3) 0.1057(3) 0.7058(3) 0.0573(11) Uani 1 1 d .
O1 O 0.6782(4) 0.0197(4) 1.0276(4) 0.0867(14) Uani 1 1 d .
O2 O 0.7712(4) 0.1416(4) 1.0719(4) 0.1014(17) Uani 1 1 d .
H2 H 0.8024 0.0950 1.0906 0.152 Uiso 1 1 calc R
O3 O 0.8830(6) 0.0200(6) 1.1606(6) 0.140(3) Uani 1 1 d .
H3A H 0.8451 0.0402 1.1966 0.210 Uiso 1 1 calc R
F1 F 0.1780(5) 0.8613(9) 0.6770(4) 0.241(5) Uani 1 1 d .
F2 F 0.2347(5) 0.8891(7) 0.5440(4) 0.194(3) Uani 1 1 d .
F3 F 0.2521(11) 0.9919(7) 0.6562(11) 0.296(7) Uani 1 1 d .
F4 F 0.3659(4) 0.9222(9) 0.6080(5) 0.215(4) Uani 1 1 d .
F5 F 0.3097(5) 0.8780(9) 0.7358(4) 0.221(4) Uani 1 1 d .
F6 F 0.2952(14) 0.7856(7) 0.6201(8) 0.379(9) Uani 1 1 d .
P1 P 0.27208(16) 0.88583(19) 0.64164(14) 0.0943(6) Uani 1 1 d .
S1 S 0.54622(10) 0.04844(11) 0.89426(10) 0.0561(4) Uani 1 1 d .
Cl1 Cl 0.73637(10) 0.17189(11) 0.81296(11) 0.0675(4) Uani 1 1 d .
Ir1 Ir 0.658509(14) 0.019288(17) 0.783741(14) 0.04951(10) 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
Cl Cl 0.1484 0.1585 '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
C2 C1 C6 118.6(6)
C2 C1 S1 121.9(5)
C6 C1 S1 119.5(5)
C3 C2 C1 121.5(6)
C3 C2 H2A 119.2
C1 C2 H2A 119.2
C2 C3 C4 120.3(7)
C2 C3 H3 119.9
C4 C3 H3 119.9
C5 C4 C3 118.7(7)
C5 C4 H4 120.6
C3 C4 H4 120.6
C4 C5 C6 122.3(7)
C4 C5 H5 118.9
C6 C5 H5 118.9
C5 C6 C1 118.5(6)
C5 C6 C7 119.0(6)
C1 C6 C7 122.4(6)
O1 C7 O2 122.9(7)
O1 C7 C6 123.1(6)
O2 C7 C6 114.1(7)
C9 C8 S1 113.0(4)
C9 C8 H8A 109.0
S1 C8 H8A 109.0
C9 C8 H8B 109.0
S1 C8 H8B 109.0
H8A C8 H8B 107.8
N1 C9 C10 119.8(6)
N1 C9 C8 116.1(5)
C10 C9 C8 124.0(6)
C11 C10 C9 120.3(7)
C11 C10 H10 119.9
C9 C10 H10 119.9
C12 C11 C10 119.0(7)
C12 C11 H11 120.5
C10 C11 H11 120.5
C13 C12 C11 118.8(7)
C13 C12 H12 120.6
C11 C12 H12 120.6
N1 C13 C12 123.1(7)
N1 C13 H13 118.4
C12 C13 H13 118.4
C15 C14 C18 107.4(5)
C15 C14 C20 128.5(7)
C18 C14 C20 123.9(7)
C15 C14 Ir1 71.5(3)
C18 C14 Ir1 70.7(3)
C20 C14 Ir1 126.2(5)
C14 C15 C16 108.6(6)
C14 C15 C21 126.4(7)
C16 C15 C21 125.0(7)
C14 C15 Ir1 70.6(3)
C16 C15 Ir1 69.1(3)
C21 C15 Ir1 127.3(5)
C17 C16 C15 107.5(6)
C17 C16 C22 125.2(7)
C15 C16 C22 126.3(7)
C17 C16 Ir1 72.7(3)
C15 C16 Ir1 72.3(3)
C22 C16 Ir1 129.6(5)
C18 C17 C16 108.4(5)
C18 C17 C23 126.9(7)
C16 C17 C23 124.7(7)
C18 C17 Ir1 70.5(3)
C16 C17 Ir1 69.0(3)
C23 C17 Ir1 127.5(4)
C17 C18 C14 107.8(6)
C17 C18 C19 128.0(6)
C14 C18 C19 124.1(6)
C17 C18 Ir1 71.7(3)
C14 C18 Ir1 70.4(3)
C19 C18 Ir1 124.9(5)
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C14 C20 H20A 109.5
C14 C20 H20B 109.5
H20A C20 H20B 109.5
C14 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C15 C21 H21A 109.5
C15 C21 H21B 109.5
H21A C21 H21B 109.5
C15 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
C16 C22 H22A 109.5
C16 C22 H22B 109.5
H22A C22 H22B 109.5
C16 C22 H22C 109.5
H22A C22 H22C 109.5
H22B C22 H22C 109.5
C17 C23 H23A 109.5
C17 C23 H23B 109.5
H23A C23 H23B 109.5
C17 C23 H23C 109.5
H23A C23 H23C 109.5
H23B C23 H23C 109.5
O3 C24 H24A 109.5
O3 C24 H24B 109.5
H24A C24 H24B 109.5
O3 C24 H24C 109.5
H24A C24 H24C 109.5
H24B C24 H24C 109.5
C13 N1 C9 118.9(5)
C13 N1 Ir1 120.5(4)
C9 N1 Ir1 120.6(4)
C7 O2 H2 109.5
C24 O3 H3A 109.5
F6 P1 F3 174.8(9)
F6 P1 F5 93.4(7)
F3 P1 F5 90.0(8)
F6 P1 F1 95.1(9)
F3 P1 F1 88.8(7)
F5 P1 F1 88.7(4)
F6 P1 F4 90.8(9)
F3 P1 F4 85.3(7)
F5 P1 F4 90.8(4)
F1 P1 F4 174.1(7)
F6 P1 F2 84.0(6)
F3 P1 F2 92.5(8)
F5 P1 F2 177.4(6)
F1 P1 F2 91.5(4)
F4 P1 F2 89.2(4)
C1 S1 C8 102.9(3)
C1 S1 Ir1 112.95(17)
C8 S1 Ir1 95.1(2)
N1 Ir1 C16 109.9(2)
N1 Ir1 C14 117.4(2)
C16 Ir1 C14 64.7(2)
N1 Ir1 C18 156.3(2)
C16 Ir1 C18 64.5(2)
C14 Ir1 C18 38.9(2)
N1 Ir1 C15 96.9(2)
C16 Ir1 C15 38.6(2)
C14 Ir1 C15 37.9(2)
C18 Ir1 C15 63.9(2)
N1 Ir1 C17 147.2(2)
C16 Ir1 C17 38.4(3)
C14 Ir1 C17 64.0(2)
C18 Ir1 C17 37.8(2)
C15 Ir1 C17 63.5(2)
N1 Ir1 S1 81.78(14)
C16 Ir1 S1 102.82(18)
C14 Ir1 S1 159.34(17)
C18 Ir1 S1 121.71(17)
C15 Ir1 S1 138.59(19)
C17 Ir1 S1 95.81(16)
N1 Ir1 Cl1 85.33(13)
C16 Ir1 Cl1 158.94(17)
C14 Ir1 Cl1 95.68(18)
C18 Ir1 Cl1 95.63(17)
C15 Ir1 Cl1 127.86(19)
C17 Ir1 Cl1 127.49(19)
S1 Ir1 Cl1 93.44(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.376(8)
C1 C6 1.405(8)
C1 S1 1.806(6)
C2 C3 1.373(9)
C2 H2A 0.9300
C3 C4 1.379(9)
C3 H3 0.9300
C4 C5 1.363(10)
C4 H4 0.9300
C5 C6 1.388(9)
C5 H5 0.9300
C6 C7 1.476(9)
C7 O1 1.209(8)
C7 O2 1.315(8)
C8 C9 1.484(9)
C8 S1 1.821(6)
C8 H8A 0.9700
C8 H8B 0.9700
C9 N1 1.348(7)
C9 C10 1.390(9)
C10 C11 1.365(10)
C10 H10 0.9300
C11 C12 1.364(10)
C11 H11 0.9300
C12 C13 1.363(9)
C12 H12 0.9300
C13 N1 1.331(7)
C13 H13 0.9300
C14 C15 1.415(9)
C14 C18 1.448(8)
C14 C20 1.495(10)
C14 Ir1 2.173(5)
C15 C16 1.432(9)
C15 C21 1.512(9)
C15 Ir1 2.186(6)
C16 C17 1.427(9)
C16 C22 1.515(9)
C16 Ir1 2.145(6)
C17 C18 1.416(8)
C17 C23 1.505(8)
C17 Ir1 2.194(5)
C18 C19 1.509(9)
C18 Ir1 2.177(5)
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
C20 H20A 0.9600
C20 H20B 0.9600
C20 H20C 0.9600
C21 H21A 0.9600
C21 H21B 0.9600
C21 H21C 0.9600
C22 H22A 0.9600
C22 H22B 0.9600
C22 H22C 0.9600
C23 H23A 0.9600
C23 H23B 0.9600
C23 H23C 0.9600
C24 O3 1.299(12)
C24 H24A 0.9600
C24 H24B 0.9600
C24 H24C 0.9600
N1 Ir1 2.099(4)
O2 H2 0.8200
O3 H3A 0.8200
F1 P1 1.506(6)
F2 P1 1.545(6)
F3 P1 1.472(9)
F4 P1 1.536(7)
F5 P1 1.501(5)
F6 P1 1.426(9)
S1 Ir1 2.3637(14)
Cl1 Ir1 2.3791(15)
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
C6 C1 C2 C3 -2.7(9)
S1 C1 C2 C3 175.4(5)
C1 C2 C3 C4 1.9(10)
C2 C3 C4 C5 0.3(11)
C3 C4 C5 C6 -1.6(11)
C4 C5 C6 C1 0.7(10)
C4 C5 C6 C7 -176.2(6)
C2 C1 C6 C5 1.4(8)
S1 C1 C6 C5 -176.7(5)
C2 C1 C6 C7 178.2(5)
S1 C1 C6 C7 0.0(7)
C5 C6 C7 O1 155.2(7)
C1 C6 C7 O1 -21.6(10)
C5 C6 C7 O2 -25.8(8)
C1 C6 C7 O2 157.5(6)
S1 C8 C9 N1 30.9(7)
S1 C8 C9 C10 -150.9(5)
N1 C9 C10 C11 2.6(10)
C8 C9 C10 C11 -175.6(6)
C9 C10 C11 C12 -2.1(11)
C10 C11 C12 C13 -0.2(11)
C11 C12 C13 N1 2.1(11)
C18 C14 C15 C16 3.1(7)
C20 C14 C15 C16 179.1(6)
Ir1 C14 C15 C16 -58.9(4)
C18 C14 C15 C21 -175.5(6)
C20 C14 C15 C21 0.5(11)
Ir1 C14 C15 C21 122.5(7)
C18 C14 C15 Ir1 62.0(4)
C20 C14 C15 Ir1 -122.0(7)
C14 C15 C16 C17 -4.8(7)
C21 C15 C16 C17 173.8(6)
Ir1 C15 C16 C17 -64.6(4)
C14 C15 C16 C22 -173.7(6)
C21 C15 C16 C22 4.9(10)
Ir1 C15 C16 C22 126.5(6)
C14 C15 C16 Ir1 59.8(4)
C21 C15 C16 Ir1 -121.6(6)
C15 C16 C17 C18 4.7(6)
C22 C16 C17 C18 173.7(6)
Ir1 C16 C17 C18 -59.6(4)
C15 C16 C17 C23 -173.9(6)
C22 C16 C17 C23 -4.9(10)
Ir1 C16 C17 C23 121.7(6)
C15 C16 C17 Ir1 64.3(4)
C22 C16 C17 Ir1 -126.7(6)
C16 C17 C18 C14 -2.8(6)
C23 C17 C18 C14 175.8(6)
Ir1 C17 C18 C14 -61.5(4)
C16 C17 C18 C19 179.1(6)
C23 C17 C18 C19 -2.3(10)
Ir1 C17 C18 C19 120.4(7)
C16 C17 C18 Ir1 58.7(4)
C23 C17 C18 Ir1 -122.7(6)
C15 C14 C18 C17 -0.2(7)
C20 C14 C18 C17 -176.4(6)
Ir1 C14 C18 C17 62.4(4)
C15 C14 C18 C19 178.0(6)
C20 C14 C18 C19 1.8(10)
Ir1 C14 C18 C19 -119.5(6)
C15 C14 C18 Ir1 -62.5(4)
C20 C14 C18 Ir1 121.3(6)
C12 C13 N1 C9 -1.7(9)
C12 C13 N1 Ir1 179.5(5)
C10 C9 N1 C13 -0.7(8)
C8 C9 N1 C13 177.6(5)
C10 C9 N1 Ir1 178.2(4)
C8 C9 N1 Ir1 -3.5(7)
C2 C1 S1 C8 4.6(5)
C6 C1 S1 C8 -177.3(4)
C2 C1 S1 Ir1 105.9(4)
C6 C1 S1 Ir1 -76.0(4)
C9 C8 S1 C1 77.6(5)
C9 C8 S1 Ir1 -37.3(5)
C13 N1 Ir1 C16 -97.8(5)
C9 N1 Ir1 C16 83.3(5)
C13 N1 Ir1 C14 -26.7(5)
C9 N1 Ir1 C14 154.5(4)
C13 N1 Ir1 C18 -26.1(8)
C9 N1 Ir1 C18 155.1(5)
C13 N1 Ir1 C15 -60.3(5)
C9 N1 Ir1 C15 120.8(5)
C13 N1 Ir1 C17 -110.6(5)
C9 N1 Ir1 C17 70.6(6)
C13 N1 Ir1 S1 161.5(5)
C9 N1 Ir1 S1 -17.4(4)
C13 N1 Ir1 Cl1 67.3(5)
C9 N1 Ir1 Cl1 -111.6(4)
C17 C16 Ir1 N1 -168.9(3)
C15 C16 Ir1 N1 75.6(4)
C22 C16 Ir1 N1 -47.2(8)
C17 C16 Ir1 C14 79.4(4)
C15 C16 Ir1 C14 -36.1(4)
C22 C16 Ir1 C14 -158.9(8)
C17 C16 Ir1 C18 36.1(4)
C15 C16 Ir1 C18 -79.4(4)
C22 C16 Ir1 C18 157.8(8)
C17 C16 Ir1 C15 115.5(5)
C22 C16 Ir1 C15 -122.8(9)
C15 C16 Ir1 C17 -115.5(5)
C22 C16 Ir1 C17 121.7(9)
C17 C16 Ir1 S1 -83.1(4)
C15 C16 Ir1 S1 161.4(3)
C22 C16 Ir1 S1 38.6(8)
C17 C16 Ir1 Cl1 56.6(7)
C15 C16 Ir1 Cl1 -59.0(8)
C22 C16 Ir1 Cl1 178.2(5)
C15 C14 Ir1 N1 -63.6(4)
C18 C14 Ir1 N1 179.6(3)
C20 C14 Ir1 N1 61.1(7)
C15 C14 Ir1 C16 36.8(4)
C18 C14 Ir1 C16 -80.0(4)
C20 C14 Ir1 C16 161.5(8)
C15 C14 Ir1 C18 116.8(5)
C20 C14 Ir1 C18 -118.5(8)
C18 C14 Ir1 C15 -116.8(5)
C20 C14 Ir1 C15 124.7(9)
C15 C14 Ir1 C17 79.6(4)
C18 C14 Ir1 C17 -37.3(4)
C20 C14 Ir1 C17 -155.7(8)
C15 C14 Ir1 S1 93.0(6)
C18 C14 Ir1 S1 -23.8(7)
C20 C14 Ir1 S1 -142.3(6)
C15 C14 Ir1 Cl1 -151.2(4)
C18 C14 Ir1 Cl1 91.9(4)
C20 C14 Ir1 Cl1 -26.5(7)
C17 C18 Ir1 N1 -118.3(5)
C14 C18 Ir1 N1 -0.9(7)
C19 C18 Ir1 N1 117.7(7)
C17 C18 Ir1 C16 -36.7(4)
C14 C18 Ir1 C16 80.7(4)
C19 C18 Ir1 C16 -160.8(7)
C17 C18 Ir1 C14 -117.4(5)
C19 C18 Ir1 C14 118.6(8)
C17 C18 Ir1 C15 -79.8(4)
C14 C18 Ir1 C15 37.6(4)
C19 C18 Ir1 C15 156.2(7)
C14 C18 Ir1 C17 117.4(5)
C19 C18 Ir1 C17 -124.1(8)
C17 C18 Ir1 S1 53.0(4)
C14 C18 Ir1 S1 170.4(3)
C19 C18 Ir1 S1 -71.1(6)
C17 C18 Ir1 Cl1 150.5(4)
C14 C18 Ir1 Cl1 -92.1(4)
C19 C18 Ir1 Cl1 26.5(6)
C14 C15 Ir1 N1 126.8(4)
C16 C15 Ir1 N1 -113.5(4)
C21 C15 Ir1 N1 5.3(7)
C14 C15 Ir1 C16 -119.7(5)
C21 C15 Ir1 C16 118.8(9)
C16 C15 Ir1 C14 119.7(5)
C21 C15 Ir1 C14 -121.5(9)
C14 C15 Ir1 C18 -38.6(4)
C16 C15 Ir1 C18 81.1(4)
C21 C15 Ir1 C18 -160.1(8)
C14 C15 Ir1 C17 -81.0(4)
C16 C15 Ir1 C17 38.7(4)
C21 C15 Ir1 C17 157.5(8)
C14 C15 Ir1 S1 -147.8(3)
C16 C15 Ir1 S1 -28.1(5)
C21 C15 Ir1 S1 90.7(7)
C14 C15 Ir1 Cl1 37.3(4)
C16 C15 Ir1 Cl1 157.0(3)
C21 C15 Ir1 Cl1 -84.2(7)
C18 C17 Ir1 N1 139.2(4)
C16 C17 Ir1 N1 19.5(6)
C23 C17 Ir1 N1 -98.7(7)
C18 C17 Ir1 C16 119.7(5)
C23 C17 Ir1 C16 -118.2(8)
C18 C17 Ir1 C14 38.3(4)
C16 C17 Ir1 C14 -81.4(4)
C23 C17 Ir1 C14 160.4(8)
C16 C17 Ir1 C18 -119.7(5)
C23 C17 Ir1 C18 122.1(8)
C18 C17 Ir1 C15 80.7(4)
C16 C17 Ir1 C15 -39.0(4)
C23 C17 Ir1 C15 -157.2(8)
C18 C17 Ir1 S1 -136.9(4)
C16 C17 Ir1 S1 103.3(4)
C23 C17 Ir1 S1 -14.9(7)
C18 C17 Ir1 Cl1 -38.1(4)
C16 C17 Ir1 Cl1 -157.8(3)
C23 C17 Ir1 Cl1 84.0(7)
C1 S1 Ir1 N1 -80.3(3)
C8 S1 Ir1 N1 26.0(3)
C1 S1 Ir1 C16 171.0(3)
C8 S1 Ir1 C16 -82.7(3)
C1 S1 Ir1 C14 120.6(5)
C8 S1 Ir1 C14 -133.1(6)
C1 S1 Ir1 C18 103.2(3)
C8 S1 Ir1 C18 -150.4(3)
C1 S1 Ir1 C15 -171.5(3)
C8 S1 Ir1 C15 -65.2(3)
C1 S1 Ir1 C17 132.7(3)
C8 S1 Ir1 C17 -121.0(3)
C1 S1 Ir1 Cl1 4.5(2)
C8 S1 Ir1 Cl1 110.8(2)
