#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:22:20 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178947 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/76/4117635.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_4117635
loop_
_publ_author_name
'Wen-Bo Liu'
'Chao Zheng'
'Chun-Xiang Zhuo'
'Li-Xin Dai'
'Shu-Li You'
_publ_section_title
;
 Iridium-Catalyzed Allylic Alkylation Reaction with N-Aryl Phosphoramidite
 Ligands: Scope and Mechanistic Studies
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4812
_journal_page_last               4821
_journal_paper_doi               10.1021/ja210923k
_journal_volume                  134
_journal_year                    2012
_chemical_formula_sum            'C52 H59 Cl2 F3 Ir N O5 P S'
_chemical_formula_weight         1161.13
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.829(2)
_cell_angle_beta                 95.085(2)
_cell_angle_gamma                109.8590(10)
_cell_formula_units_Z            2
_cell_length_a                   11.5909(12)
_cell_length_b                   12.9494(13)
_cell_length_c                   17.5333(17)
_cell_measurement_reflns_used    9894
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.36
_cell_volume                     2434.0(4)
_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-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      133(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17261
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.69
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.988
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.4676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_description       block
_exptl_crystal_F_000             1174
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.513
_refine_diff_density_min         -2.515
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         10449
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      0.927
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0418
_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)+(0.0880P)²+3.7067P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1213
_reflns_number_gt                9011
_reflns_number_total             10449
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja210923k_K2a.cif
_cod_data_source_block           mo_dm11194_0m
_cod_database_code               4117635
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir -0.014068(17) 0.793946(15) 0.634996(11) 0.01708(8) Uani 1 1 d . A .
N1 N 0.1553(4) 0.9798(4) 0.7705(3) 0.0240(10) Uani 1 1 d . . .
P1 P 0.16101(12) 0.86590(11) 0.72260(8) 0.0179(3) Uani 1 1 d . A .
O1 O 0.2894(3) 0.8926(3) 0.6869(2) 0.0233(8) Uani 1 1 d . . .
O2 O 0.1850(3) 0.8041(3) 0.7942(2) 0.0221(8) Uani 1 1 d . . .
O3 O 0.6853(5) 0.4150(4) 0.6284(3) 0.0430(11) Uani 1 1 d . . .
O4 O 0.7027(4) 0.2409(3) 0.6553(3) 0.0346(10) Uani 1 1 d . . .
O5 O 0.8826(4) 0.4102(5) 0.6796(3) 0.0530(14) Uani 1 1 d . . .
S1 S 0.75155(12) 0.35959(11) 0.67215(8) 0.0243(3) Uani 1 1 d . . .
F1 F 0.7780(5) 0.3427(4) 0.8186(3) 0.0705(15) Uani 1 1 d . . .
F2 F 0.5981(5) 0.3363(4) 0.7753(3) 0.0639(14) Uani 1 1 d . . .
F3 F 0.7515(7) 0.4919(4) 0.7975(3) 0.091(2) Uani 1 1 d . . .
C1 C -0.1079(5) 0.7004(4) 0.7232(3) 0.0228(11) Uani 1 1 d . . .
H1A H -0.1334 0.6184 0.7119 0.027 Uiso 1 1 calc R . .
H1B H -0.0731 0.7316 0.7780 0.027 Uiso 1 1 calc R . .
C2 C -0.1877(5) 0.7480(5) 0.6872(4) 0.0263(12) Uani 1 1 d . . .
H2A H -0.2086 0.8074 0.7184 0.032 Uiso 1 1 calc R . .
C3 C -0.2257(5) 0.7230(5) 0.6073(4) 0.0268(12) Uani 1 1 d . . .
H3A H -0.2657 0.7708 0.5844 0.032 Uiso 1 1 calc R . .
H3B H -0.2639 0.6433 0.5847 0.032 Uiso 1 1 calc R . .
C4 C 0.1021(5) 0.8673(4) 0.5455(3) 0.0203(10) Uani 1 1 d . . .
H4A H 0.1470 0.9494 0.5589 0.024 Uiso 1 1 calc R . .
C5 C -0.0226(5) 0.8375(4) 0.5158(3) 0.0205(10) Uani 1 1 d . . .
H5A H -0.0494 0.9026 0.5120 0.025 Uiso 1 1 calc R . .
C6 C -0.0951(5) 0.7364(5) 0.4553(3) 0.0284(12) Uani 1 1 d . . .
H6A H -0.0695 0.7516 0.4042 0.034 Uiso 1 1 calc R . .
H6B H -0.1842 0.7259 0.4522 0.034 Uiso 1 1 calc R . .
C7 C -0.0786(6) 0.6275(5) 0.4709(3) 0.0286(12) Uani 1 1 d . . .
H7A H -0.1554 0.5647 0.4484 0.034 Uiso 1 1 calc R . .
H7B H -0.0107 0.6184 0.4436 0.034 Uiso 1 1 calc R . .
C8 C -0.0498(5) 0.6207(4) 0.5560(3) 0.0259(12) Uani 1 1 d . . .
H8A H -0.1100 0.5554 0.5738 0.031 Uiso 1 1 calc R . .
C9 C 0.0694(5) 0.6538(4) 0.5941(3) 0.0253(11) Uani 1 1 d . . .
H9A H 0.0804 0.6086 0.6347 0.030 Uiso 1 1 calc R . .
C10 C 0.1821(6) 0.7028(5) 0.5562(4) 0.0305(12) Uani 1 1 d U . .
H10A H 0.1891 0.6441 0.5172 0.037 Uiso 1 1 calc R . .
H10B H 0.2561 0.7269 0.5960 0.037 Uiso 1 1 calc R . .
C11 C 0.1826(5) 0.8029(5) 0.5158(3) 0.0276(12) Uani 1 1 d U . .
H11A H 0.2691 0.8554 0.5215 0.033 Uiso 1 1 calc R . .
H11B H 0.1549 0.7756 0.4597 0.033 Uiso 1 1 calc R . .
C12 C 0.0642(5) 1.0191(4) 0.7374(3) 0.0208(10) Uani 1 1 d U A .
C13 C -0.0202(4) 0.9515(4) 0.6732(3) 0.0180(10) Uani 1 1 d U . .
C14 C -0.1067(5) 0.9925(5) 0.6412(3) 0.0245(11) Uani 1 1 d . . .
H14 H -0.1649 0.9486 0.5979 0.029 Uiso 1 1 calc R . .
C15 C -0.1107(6) 1.0954(5) 0.6707(4) 0.0295(13) Uani 1 1 d . . .
H15 H -0.1705 1.1215 0.6475 0.035 Uiso 1 1 calc R A .
C16 C -0.0279(7) 1.1588(5) 0.7333(4) 0.0368(15) Uani 1 1 d . A .
H16 H -0.0308 1.2293 0.7531 0.044 Uiso 1 1 calc R . .
C17 C 0.0617(7) 1.1225(5) 0.7692(4) 0.0349(14) Uani 1 1 d . . .
C18 C 0.1194(15) 1.1778(11) 0.8501(9) 0.038(3) Uani 0.50 1 d PDU A 1
H18A H 0.0560 1.1924 0.8795 0.045 Uiso 0.50 1 calc PR A 1
H18B H 0.1853 1.2500 0.8487 0.045 Uiso 0.50 1 calc PR A 1
C21 C 0.3418(14) 1.1550(12) 0.8098(10) 0.052(4) Uani 0.50 1 d PU A 1
H21A H 0.3871 1.1255 0.7736 0.077 Uiso 0.50 1 calc PR A 1
H21B H 0.4001 1.2039 0.8541 0.077 Uiso 0.50 1 calc PR A 1
H21C H 0.2995 1.1974 0.7833 0.077 Uiso 0.50 1 calc PR A 1
C20 C 0.246(3) 1.0586(19) 0.838(2) 0.030(3) Uani 0.50 1 d PU A 1
H20A H 0.2896 1.0168 0.8669 0.037 Uiso 0.50 1 calc PR A 1
C19 C 0.1750(12) 1.1025(10) 0.8906(8) 0.040(2) Uani 0.50 1 d PDU A 1
H19A H 0.2300 1.1457 0.9387 0.048 Uiso 0.50 1 calc PR A 1
H19B H 0.1077 1.0401 0.9049 0.048 Uiso 0.50 1 calc PR A 1
C18' C 0.1738(11) 1.2013(9) 0.8307(8) 0.027(2) Uani 0.50 1 d PDU A 2
H18C H 0.1987 1.2646 0.8162 0.033 Uiso 0.50 1 d PR A 2
H18D H 0.1441 1.2109 0.8814 0.033 Uiso 0.50 1 d PR A 2
C19' C 0.2808(10) 1.1607(9) 0.8404(7) 0.029(2) Uani 0.50 1 d PDU A 2
H19C H 0.3356 1.2009 0.8892 0.035 Uiso 0.50 1 calc PR A 2
H19D H 0.3296 1.1773 0.7970 0.035 Uiso 0.50 1 calc PR A 2
C20' C 0.237(3) 1.0368(18) 0.842(2) 0.029(3) Uani 0.50 1 d PU A 2
H20B H 0.3104 1.0129 0.8450 0.035 Uiso 0.50 1 calc PR A 2
C21' C 0.1708(11) 1.0075(10) 0.9132(7) 0.031(2) Uani 0.50 1 d PU A 2
H21D H 0.1449 0.9272 0.9132 0.046 Uiso 0.50 1 calc PR A 2
H21E H 0.0978 1.0297 0.9109 0.046 Uiso 0.50 1 calc PR A 2
H21F H 0.2275 1.0470 0.9607 0.046 Uiso 0.50 1 calc PR A 2
C22 C 0.4066(5) 0.9129(4) 0.7296(3) 0.0217(11) Uani 1 1 d . A .
C23 C 0.4965(6) 1.0172(5) 0.7281(4) 0.0319(13) Uani 1 1 d . . .
H23 H 0.4764 1.0709 0.7027 0.038 Uiso 1 1 calc R A .
C24 C 0.6153(6) 1.0398(5) 0.7645(4) 0.0390(15) Uani 1 1 d . A .
H24 H 0.6787 1.1084 0.7620 0.047 Uiso 1 1 calc R . .
C25 C 0.6429(5) 0.9621(5) 0.8051(3) 0.0288(12) Uani 1 1 d . . .
C26 C 0.7653(6) 0.9858(6) 0.8444(4) 0.0380(15) Uani 1 1 d . A .
H26 H 0.8287 1.0547 0.8427 0.046 Uiso 1 1 calc R . .
C27 C 0.7912(6) 0.9106(6) 0.8839(4) 0.0411(16) Uani 1 1 d . . .
H27 H 0.8731 0.9267 0.9084 0.049 Uiso 1 1 calc R A .
C28 C 0.6991(5) 0.8100(6) 0.8889(4) 0.0330(13) Uani 1 1 d . A .
H28 H 0.7178 0.7590 0.9180 0.040 Uiso 1 1 calc R . .
C29 C 0.5802(5) 0.7845(5) 0.8513(3) 0.0272(12) Uani 1 1 d . . .
H29 H 0.5177 0.7163 0.8557 0.033 Uiso 1 1 calc R A .
C30 C 0.5499(5) 0.8576(5) 0.8069(3) 0.0224(11) Uani 1 1 d . A .
C31 C 0.4290(5) 0.8322(4) 0.7640(3) 0.0209(10) Uani 1 1 d . . .
C32 C 0.3320(5) 0.7207(4) 0.7585(3) 0.0208(10) Uani 1 1 d . A .
C33 C 0.2168(5) 0.7096(5) 0.7793(3) 0.0230(11) Uani 1 1 d . A .
C34 C 0.1287(5) 0.6068(5) 0.7850(4) 0.0301(13) Uani 1 1 d . . .
H34 H 0.0518 0.6029 0.8017 0.036 Uiso 1 1 calc R A .
C35 C 0.1537(5) 0.5116(5) 0.7665(4) 0.0320(13) Uani 1 1 d . A .
H35 H 0.0955 0.4421 0.7728 0.038 Uiso 1 1 calc R . .
C36 C 0.2646(5) 0.5158(5) 0.7381(3) 0.0292(13) Uani 1 1 d . . .
C37 C 0.2885(7) 0.4172(5) 0.7124(4) 0.0415(17) Uani 1 1 d . A .
H37 H 0.2294 0.3467 0.7159 0.050 Uiso 1 1 calc R . .
C38 C 0.3939(8) 0.4227(6) 0.6832(5) 0.053(2) Uani 1 1 d . . .
H38 H 0.4090 0.3562 0.6678 0.064 Uiso 1 1 calc R A .
C39 C 0.4809(7) 0.5248(6) 0.6754(4) 0.0452(18) Uani 1 1 d . A .
H39 H 0.5537 0.5273 0.6535 0.054 Uiso 1 1 calc R . .
C40 C 0.4616(6) 0.6220(5) 0.6995(4) 0.0347(14) Uani 1 1 d . . .
H40 H 0.5207 0.6912 0.6934 0.042 Uiso 1 1 calc R A .
C41 C 0.3549(5) 0.6200(4) 0.7330(3) 0.0242(11) Uani 1 1 d . A .
C42 C 0.7193(7) 0.3842(5) 0.7709(4) 0.0433(17) Uani 1 1 d . . .
C43 C 0.5199(8) 0.8252(10) 0.4735(5) 0.073(3) Uani 1 1 d . . .
H43A H 0.4884 0.7441 0.4741 0.088 Uiso 1 1 calc R . .
H43B H 0.4552 0.8435 0.4432 0.088 Uiso 1 1 calc R . .
C45 C 0.6096(11) 0.5202(9) 0.9690(6) 0.076(3) Uani 1 1 d . . .
H45A H 0.6854 0.5355 0.9479 0.091 Uiso 1 1 calc R . .
C46 C 0.4984(10) 0.4969(7) 0.9205(5) 0.060(2) Uani 1 1 d . . .
H46A H 0.4974 0.4934 0.8660 0.072 Uiso 1 1 calc R . .
C47 C 0.3917(10) 0.4794(9) 0.9520(6) 0.071(3) Uani 1 1 d . . .
H47A H 0.3168 0.4666 0.9193 0.085 Uiso 1 1 calc R . .
C48 C 0.0149(10) 0.2629(10) 0.0357(6) 0.075(3) Uani 1 1 d U . .
H48A H 0.0169 0.1961 0.0040 0.112 Uiso 1 1 calc R . .
H48B H -0.0585 0.2433 0.0625 0.112 Uiso 1 1 calc R . .
H48C H 0.0896 0.2946 0.0741 0.112 Uiso 1 1 calc R . .
C49 C 0.0093(13) 0.3534(12) -0.0194(8) 0.101(3) Uani 1 1 d U . .
H49A H 0.0841 0.3732 -0.0458 0.121 Uiso 1 1 calc R . .
H49B H -0.0638 0.3191 -0.0598 0.121 Uiso 1 1 calc R . .
C50 C 0.0016(12) 0.4590(11) 0.0243(7) 0.093(3) Uani 1 1 d U . .
H50A H -0.0738 0.4392 0.0501 0.111 Uiso 1 1 calc R . .
H50B H 0.0740 0.4926 0.0653 0.111 Uiso 1 1 calc R . .
C51 C 0.6377(11) 0.2522(9) 0.9847(8) 0.092(4) Uani 1 1 d D . .
H51A H 0.7210 0.3050 1.0053 0.137 Uiso 1 1 calc R . .
H51B H 0.5760 0.2799 1.0053 0.137 Uiso 1 1 calc R . .
H51C H 0.6260 0.2444 0.9280 0.137 Uiso 1 1 calc R . .
C52 C 0.6231(11) 0.1449(10) 1.0076(7) 0.094(4) Uani 1 1 d D . .
H52A H 0.6412 0.1575 1.0649 0.113 Uiso 1 1 calc R . .
H52B H 0.6892 0.1216 0.9876 0.113 Uiso 1 1 calc R . .
C53 C 0.5076(10) 0.0497(8) 0.9861(5) 0.073(3) Uani 1 1 d . . .
H53A H 0.4402 0.0747 1.0017 0.087 Uiso 1 1 calc R . .
H53B H 0.4935 0.0322 0.9287 0.087 Uiso 1 1 calc R . .
Cl1 Cl 0.5477(2) 0.8957(3) 0.56901(13) 0.0808(9) Uani 1 1 d . . .
Cl2 Cl 0.65283(16) 0.86018(13) 0.42855(11) 0.0419(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'
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'
Cl Cl 0.1484 0.1585 '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'
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
C13 Ir1 C2 79.1(2) . .
C13 Ir1 C1 100.4(2) . .
C2 Ir1 C1 37.4(2) . .
C13 Ir1 C5 86.4(2) . .
C2 Ir1 C5 117.2(2) . .
C1 Ir1 C5 149.1(2) . .
C13 Ir1 C4 88.8(2) . .
C2 Ir1 C4 152.3(2) . .
C1 Ir1 C4 169.03(19) . .
C5 Ir1 C4 36.37(19) . .
C13 Ir1 P1 79.82(14) . .
C2 Ir1 P1 114.34(16) . .
C1 Ir1 P1 88.43(15) . .
C5 Ir1 P1 122.51(14) . .
C4 Ir1 P1 87.46(14) . .
C13 Ir1 C3 90.2(2) . .
C2 Ir1 C3 36.1(2) . .
C1 Ir1 C3 65.9(2) . .
C5 Ir1 C3 84.1(2) . .
C4 Ir1 C3 120.4(2) . .
P1 Ir1 C3 150.38(16) . .
C13 Ir1 C8 160.9(2) . .
C2 Ir1 C8 98.6(2) . .
C1 Ir1 C8 88.2(2) . .
C5 Ir1 C8 77.8(2) . .
C4 Ir1 C8 84.71(19) . .
P1 Ir1 C8 117.71(15) . .
C3 Ir1 C8 77.8(2) . .
C13 Ir1 C9 159.5(2) . .
C2 Ir1 C9 119.7(2) . .
C1 Ir1 C9 92.2(2) . .
C5 Ir1 C9 91.0(2) . .
C4 Ir1 C9 77.3(2) . .
P1 Ir1 C9 84.49(14) . .
C3 Ir1 C9 109.8(2) . .
C8 Ir1 C9 33.6(2) . .
C12 N1 C20' 122.4(14) . .
C12 N1 C20 115.5(14) . .
C20' N1 C20 11(2) . .
C12 N1 P1 115.4(4) . .
C20' N1 P1 122.2(14) . .
C20 N1 P1 128.4(14) . .
O1 P1 O2 101.91(19) . .
O1 P1 N1 109.8(2) . .
O2 P1 N1 99.9(2) . .
O1 P1 Ir1 115.71(15) . .
O2 P1 Ir1 122.04(15) . .
N1 P1 Ir1 106.09(17) . .
C22 O1 P1 125.3(3) . .
C33 O2 P1 118.9(3) . .
O5 S1 O4 116.0(3) . .
O5 S1 O3 113.9(3) . .
O4 S1 O3 115.2(3) . .
O5 S1 C42 103.0(3) . .
O4 S1 C42 101.5(3) . .
O3 S1 C42 104.6(3) . .
C2 C1 Ir1 71.2(3) . .
C2 C1 H1A 116.5 . .
Ir1 C1 H1A 116.5 . .
C2 C1 H1B 116.5 . .
Ir1 C1 H1B 116.5 . .
H1A C1 H1B 113.5 . .
C3 C2 C1 121.1(5) . .
C3 C2 Ir1 75.1(3) . .
C1 C2 Ir1 71.3(3) . .
C3 C2 H2A 119.2 . .
C1 C2 H2A 119.2 . .
Ir1 C2 H2A 119.2 . .
C2 C3 Ir1 68.8(3) . .
C2 C3 H3A 116.8 . .
Ir1 C3 H3A 116.8 . .
C2 C3 H3B 116.8 . .
Ir1 C3 H3B 116.8 . .
H3A C3 H3B 113.8 . .
C5 C4 C11 122.3(5) . .
C5 C4 Ir1 71.3(3) . .
C11 C4 Ir1 115.1(3) . .
C5 C4 H4A 113.8 . .
C11 C4 H4A 113.8 . .
Ir1 C4 H4A 113.8 . .
C4 C5 C6 124.9(5) . .
C4 C5 Ir1 72.3(3) . .
C6 C5 Ir1 111.8(4) . .
C4 C5 H5A 113.5 . .
C6 C5 H5A 113.5 . .
Ir1 C5 H5A 113.5 . .
C5 C6 C7 114.8(5) . .
C5 C6 H6A 108.6 . .
C7 C6 H6A 108.6 . .
C5 C6 H6B 108.6 . .
C7 C6 H6B 108.6 . .
H6A C6 H6B 107.5 . .
C8 C7 C6 114.8(5) . .
C8 C7 H7A 108.6 . .
C6 C7 H7A 108.6 . .
C8 C7 H7B 108.6 . .
C6 C7 H7B 108.6 . .
H7A C7 H7B 107.5 . .
C9 C8 C7 123.0(5) . .
C9 C8 Ir1 74.0(3) . .
C7 C8 Ir1 110.8(3) . .
C9 C8 H8A 114.1 . .
C7 C8 H8A 114.1 . .
Ir1 C8 H8A 114.1 . .
C8 C9 C10 123.2(5) . .
C8 C9 Ir1 72.4(3) . .
C10 C9 Ir1 110.1(3) . .
C8 C9 H9A 114.5 . .
C10 C9 H9A 114.5 . .
Ir1 C9 H9A 114.5 . .
C9 C10 C11 114.6(5) . .
C9 C10 H10A 108.6 . .
C11 C10 H10A 108.6 . .
C9 C10 H10B 108.6 . .
C11 C10 H10B 108.6 . .
H10A C10 H10B 107.6 . .
C4 C11 C10 116.2(5) . .
C4 C11 H11A 108.2 . .
C10 C11 H11A 108.2 . .
C4 C11 H11B 108.2 . .
C10 C11 H11B 108.2 . .
H11A C11 H11B 107.4 . .
C17 C12 C13 122.3(5) . .
C17 C12 N1 119.5(5) . .
C13 C12 N1 118.2(4) . .
C14 C13 C12 117.1(5) . .
C14 C13 Ir1 124.1(4) . .
C12 C13 Ir1 118.7(4) . .
C15 C14 C13 122.1(5) . .
C15 C14 H14 118.9 . .
C13 C14 H14 118.9 . .
C16 C15 C14 119.4(5) . .
C16 C15 H15 120.3 . .
C14 C15 H15 120.3 . .
C15 C16 C17 121.7(5) . .
C15 C16 H16 119.1 . .
C17 C16 H16 119.1 . .
C12 C17 C16 117.3(6) . .
C12 C17 C18 122.7(7) . .
C16 C17 C18 117.2(7) . .
C12 C17 C18' 118.4(7) . .
C16 C17 C18' 123.0(6) . .
C18 C17 C18' 27.5(7) . .
C17 C18 C19 109.9(9) . .
C17 C18 H18A 109.7 . .
C19 C18 H18A 109.7 . .
C17 C18 H18B 109.7 . .
C19 C18 H18B 109.7 . .
H18A C18 H18B 108.2 . .
C17 C18 H18C 86.7 . .
C19 C18 H18C 118.8 . .
H18A C18 H18C 119.2 . .
H18B C18 H18C 23.0 . .
C17 C18 H18D 167.4 . .
C19 C18 H18D 81.9 . .
H18A C18 H18D 68.8 . .
H18B C18 H18D 60.6 . .
H18C C18 H18D 83.5 . .
C20 C21 H21A 109.5 . .
C20 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C20 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C19 C20 N1 108(2) . .
C19 C20 C21 109.6(18) . .
N1 C20 C21 111(2) . .
C19 C20 H20A 109.5 . .
N1 C20 H20A 109.5 . .
C21 C20 H20A 109.5 . .
C20 C19 C18 109.9(17) . .
C20 C19 H19A 109.7 . .
C18 C19 H19A 109.7 . .
C20 C19 H19B 109.7 . .
C18 C19 H19B 109.7 . .
H19A C19 H19B 108.2 . .
C20 C19 H18D 123.4 . .
C18 C19 H18D 23.3 . .
H19A C19 H18D 86.7 . .
H19B C19 H18D 115.8 . .
C19' C18' C17 114.1(9) . .
C19' C18' H18C 109.1 . .
C17 C18' H18C 107.4 . .
C19' C18' H18D 109.4 . .
C17 C18' H18D 109.0 . .
H18C C18' H18D 107.6 . .
C18' C19' C20' 111.6(17) . .
C18' C19' H19C 109.3 . .
C20' C19' H19C 109.3 . .
C18' C19' H19D 109.3 . .
C20' C19' H19D 109.3 . .
H19C C19' H19D 108.0 . .
N1 C20' C19' 108(2) . .
N1 C20' C21' 111.1(19) . .
C19' C20' C21' 112(2) . .
N1 C20' H20B 108.7 . .
C19' C20' H20B 108.7 . .
C21' C20' H20B 108.7 . .
C20' C21' H21D 109.5 . .
C20' C21' H21E 109.5 . .
H21D C21' H21E 109.5 . .
C20' C21' H21F 109.5 . .
H21D C21' H21F 109.5 . .
H21E C21' H21F 109.5 . .
C31 C22 C23 124.0(5) . .
C31 C22 O1 120.5(5) . .
C23 C22 O1 115.3(5) . .
C24 C23 C22 118.3(6) . .
C24 C23 H23 120.8 . .
C22 C23 H23 120.8 . .
C23 C24 C25 120.5(5) . .
C23 C24 H24 119.7 . .
C25 C24 H24 119.7 . .
C24 C25 C30 120.2(5) . .
C24 C25 C26 120.9(5) . .
C30 C25 C26 118.9(6) . .
C27 C26 C25 120.6(6) . .
C27 C26 H26 119.7 . .
C25 C26 H26 119.7 . .
C26 C27 C28 120.9(6) . .
C26 C27 H27 119.6 . .
C28 C27 H27 119.6 . .
C29 C28 C27 119.9(6) . .
C29 C28 H28 120.0 . .
C27 C28 H28 120.0 . .
C28 C29 C30 121.4(6) . .
C28 C29 H29 119.3 . .
C30 C29 H29 119.3 . .
C29 C30 C25 118.2(5) . .
C29 C30 C31 123.3(5) . .
C25 C30 C31 118.5(5) . .
C22 C31 C30 118.2(5) . .
C22 C31 C32 121.2(5) . .
C30 C31 C32 120.6(5) . .
C33 C32 C41 117.5(5) . .
C33 C32 C31 120.8(5) . .
C41 C32 C31 121.7(5) . .
C32 C33 O2 119.3(5) . .
C32 C33 C34 122.7(5) . .
O2 C33 C34 118.0(5) . .
C35 C34 C33 119.8(5) . .
C35 C34 H34 120.1 . .
C33 C34 H34 120.1 . .
C34 C35 C36 120.6(5) . .
C34 C35 H35 119.7 . .
C36 C35 H35 119.7 . .
C35 C36 C41 119.8(5) . .
C35 C36 C37 121.7(6) . .
C41 C36 C37 118.5(6) . .
C38 C37 C36 120.9(6) . .
C38 C37 H37 119.6 . .
C36 C37 H37 119.6 . .
C37 C38 C39 120.9(6) . .
C37 C38 H38 119.6 . .
C39 C38 H38 119.6 . .
C40 C39 C38 120.1(7) . .
C40 C39 H39 119.9 . .
C38 C39 H39 119.9 . .
C39 C40 C41 120.7(6) . .
C39 C40 H40 119.6 . .
C41 C40 H40 119.6 . .
C40 C41 C36 118.8(5) . .
C40 C41 C32 121.9(5) . .
C36 C41 C32 119.2(5) . .
F1 C42 F3 107.6(7) . .
F1 C42 F2 106.7(6) . .
F3 C42 F2 107.4(7) . .
F1 C42 S1 111.9(6) . .
F3 C42 S1 112.0(5) . .
F2 C42 S1 111.0(5) . .
Cl2 C43 Cl1 112.1(5) . .
Cl2 C43 H43A 109.2 . .
Cl1 C43 H43A 109.2 . .
Cl2 C43 H43B 109.2 . .
Cl1 C43 H43B 109.2 . .
H43A C43 H43B 107.9 . .
C47 C45 C46 119.4(10) 2_667 .
C47 C45 H45A 120.3 2_667 .
C46 C45 H45A 120.3 . .
C47 C46 C45 119.4(9) . .
C47 C46 H46A 120.3 . .
C45 C46 H46A 120.3 . .
C46 C47 C45 121.2(9) . 2_667
C46 C47 H47A 119.4 . .
C45 C47 H47A 119.4 2_667 .
C49 C48 H48A 109.5 . .
C49 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C49 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
C50 C49 C48 113.5(10) . .
C50 C49 H49A 108.9 . .
C48 C49 H49A 108.9 . .
C50 C49 H49B 108.9 . .
C48 C49 H49B 108.9 . .
H49A C49 H49B 107.7 . .
C50 C50 C49 113.8(14) 2_565 .
C50 C50 H50A 108.8 2_565 .
C49 C50 H50A 108.8 . .
C50 C50 H50B 108.8 2_565 .
C49 C50 H50B 108.8 . .
H50A C50 H50B 107.7 . .
C52 C51 H51A 109.5 . .
C52 C51 H51B 109.5 . .
H51A C51 H51B 109.5 . .
C52 C51 H51C 109.5 . .
H51A C51 H51C 109.5 . .
H51B C51 H51C 109.5 . .
C51 C52 C53 122.0(11) . .
C51 C52 H52A 106.8 . .
C53 C52 H52A 106.8 . .
C51 C52 H52B 106.8 . .
C53 C52 H52B 106.8 . .
H52A C52 H52B 106.7 . .
C53 C53 C52 121.0(13) 2_657 .
C53 C53 H53A 107.1 2_657 .
C52 C53 H53A 107.1 . .
C53 C53 H53B 107.1 2_657 .
C52 C53 H53B 107.1 . .
H53A C53 H53B 106.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 C13 2.097(5) .
Ir1 C2 2.210(5) .
Ir1 C1 2.211(5) .
Ir1 C5 2.231(5) .
Ir1 C4 2.244(5) .
Ir1 P1 2.2733(13) .
Ir1 C3 2.291(5) .
Ir1 C8 2.378(5) .
Ir1 C9 2.398(5) .
N1 C12 1.427(7) .
N1 C20' 1.46(3) .
N1 C20 1.52(3) .
N1 P1 1.633(5) .
P1 O1 1.610(4) .
P1 O2 1.619(4) .
O1 C22 1.416(6) .
O2 C33 1.396(6) .
O3 S1 1.447(5) .
O4 S1 1.429(4) .
O5 S1 1.422(5) .
S1 C42 1.817(7) .
F1 C42 1.306(9) .
F2 C42 1.343(9) .
F3 C42 1.327(8) .
C1 C2 1.419(8) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C2 C3 1.395(8) .
C2 H2A 1.0000 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.397(7) .
C4 C11 1.532(7) .
C4 H4A 1.0000 .
C5 C6 1.519(7) .
C5 H5A 1.0000 .
C6 C7 1.538(8) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.519(8) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.380(8) .
C8 H8A 1.0000 .
C9 C10 1.497(8) .
C9 H9A 1.0000 .
C10 C11 1.547(8) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C17 1.400(8) .
C12 C13 1.407(7) .
C13 C14 1.390(7) .
C14 C15 1.389(8) .
C14 H14 0.9500 .
C15 C16 1.365(10) .
C15 H15 0.9500 .
C16 C17 1.408(9) .
C16 H16 0.9500 .
C17 C18 1.495(15) .
C17 C18' 1.576(13) .
C18 C19 1.544(14) .
C18 H18A 0.9900 .
C18 H18B 0.9900 .
C21 C20 1.53(3) .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C20 C19 1.47(4) .
C20 H20A 1.0000 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C18' C19' 1.506(13) .
C18' H18C 0.8499 .
C18' H18D 0.9900 .
C19' C20' 1.51(2) .
C19' H19C 0.9900 .
C19' H19D 0.9900 .
C20' C21' 1.54(4) .
C20' H20B 1.0000 .
C21' H21D 0.9800 .
C21' H21E 0.9800 .
C21' H21F 0.9800 .
C22 C31 1.352(8) .
C22 C23 1.404(8) .
C23 C24 1.384(9) .
C23 H23 0.9500 .
C24 C25 1.403(9) .
C24 H24 0.9500 .
C25 C30 1.421(7) .
C25 C26 1.436(8) .
C26 C27 1.356(10) .
C26 H26 0.9500 .
C27 C28 1.394(9) .
C27 H27 0.9500 .
C28 C29 1.386(8) .
C28 H28 0.9500 .
C29 C30 1.406(8) .
C29 H29 0.9500 .
C30 C31 1.442(7) .
C31 C32 1.484(7) .
C32 C33 1.380(7) .
C32 C41 1.445(7) .
C33 C34 1.397(8) .
C34 C35 1.367(9) .
C34 H34 0.9500 .
C35 C36 1.406(9) .
C35 H35 0.9500 .
C36 C41 1.418(8) .
C36 C37 1.426(8) .
C37 C38 1.349(12) .
C37 H37 0.9500 .
C38 C39 1.395(11) .
C38 H38 0.9500 .
C39 C40 1.376(9) .
C39 H39 0.9500 .
C40 C41 1.409(9) .
C40 H40 0.9500 .
C43 Cl2 1.740(9) .
C43 Cl1 1.755(9) .
C43 H43A 0.9900 .
C43 H43B 0.9900 .
C45 C47 1.387(14) 2_667
C45 C46 1.399(14) .
C45 H45A 0.9500 .
C46 C47 1.358(13) .
C46 H46A 0.9500 .
C47 C45 1.387(14) 2_667
C47 H47A 0.9500 .
C48 C49 1.619(17) .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
C49 C50 1.521(18) .
C49 H49A 0.9900 .
C49 H49B 0.9900 .
C50 C50 1.45(2) 2_565
C50 H50A 0.9900 .
C50 H50B 0.9900 .
C51 C52 1.452(13) .
C51 H51A 0.9800 .
C51 H51B 0.9800 .
C51 H51C 0.9800 .
C52 C53 1.460(15) .
C52 H52A 0.9900 .
C52 H52B 0.9900 .
C53 C53 1.39(2) 2_657
C53 H53A 0.9900 .
C53 H53B 0.9900 .
