# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1402756'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_date             2013-09-11T19:05:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C32 H33 N2 P2), 2(Cl), H2 O'
_chemical_formula_sum            'C64 H68 Cl2 N4 O P4'
_chemical_formula_weight         1104

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.5150(5)
_cell_length_b                   27.407(2)
_cell_length_c                   16.8094(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.149(2)
_cell_angle_gamma                90
_cell_volume                     2978.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      28.26

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prisms
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1164
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_T_max  0.949

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_number            40896
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             7372
_reflns_number_gt                4665
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0793P)²+1.0304P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7372
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.094
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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_
_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
P1 P 0.79480(11) 0.10395(2) 0.34231(4) 0.05359(19) Uani 1 1 d . . .
P2 P 0.31805(10) 0.32410(2) 0.49441(3) 0.04939(18) Uani 1 1 d . . .
N1 N 0.6398(3) 0.21155(7) 0.37057(11) 0.0465(4) Uani 1 1 d . . .
C2 C 0.5201(3) 0.21155(8) 0.42932(13) 0.0442(5) Uani 1 1 d . . .
N3 N 0.6235(3) 0.23422(7) 0.49211(11) 0.0460(4) Uani 1 1 d . . .
C4 C 0.8127(4) 0.24935(9) 0.47196(16) 0.0536(6) Uani 1 1 d . . .
H4 H 0.9149 0.266 0.5049 0.064 Uiso 1 1 calc R . .
C5 C 0.8209(4) 0.23558(9) 0.39602(15) 0.0536(6) Uani 1 1 d . . .
H5 H 0.9293 0.2412 0.3661 0.064 Uiso 1 1 calc R . .
C6 C 0.3124(4) 0.18975(10) 0.42524(18) 0.0618(7) Uani 1 1 d . . .
H601 H 0.2487 0.1894 0.3706 0.093 Uiso 1 1 calc R . .
H602 H 0.2293 0.2087 0.4572 0.093 Uiso 1 1 calc R . .
H603 H 0.3238 0.1569 0.4453 0.093 Uiso 1 1 calc R . .
C11 C 0.5884(4) 0.19167(9) 0.28876(13) 0.0556(6) Uani 1 1 d . . .
H111 H 0.6922 0.2026 0.2561 0.067 Uiso 1 1 calc R . .
H112 H 0.4565 0.2051 0.2657 0.067 Uiso 1 1 calc R . .
C12 C 0.5757(4) 0.13627(10) 0.28439(14) 0.0579(6) Uani 1 1 d . . .
H121 H 0.5682 0.1265 0.2287 0.069 Uiso 1 1 calc R . .
H122 H 0.4485 0.1259 0.3038 0.069 Uiso 1 1 calc R . .
C21 C 0.5496(4) 0.24534(9) 0.56958(13) 0.0545(6) Uani 1 1 d . . .
H211 H 0.6549 0.236 0.6128 0.065 Uiso 1 1 calc R . .
H212 H 0.4266 0.2262 0.5746 0.065 Uiso 1 1 calc R . .
C22 C 0.4998(4) 0.29904(9) 0.57766(13) 0.0539(6) Uani 1 1 d . . .
H221 H 0.6278 0.3175 0.5813 0.065 Uiso 1 1 calc R . .
H222 H 0.4413 0.3038 0.6274 0.065 Uiso 1 1 calc R . .
C31 C 0.6931(5) 0.09493(10) 0.43801(15) 0.0648(7) Uani 1 1 d . . .
C32 C 0.7895(6) 0.11942(13) 0.50444(16) 0.0873(11) Uani 1 1 d . . .
H32 H 0.9082 0.1376 0.5003 0.105 Uiso 1 1 calc R . .
C33 C 0.7104(11) 0.1170(2) 0.5770(2) 0.136(2) Uani 1 1 d . . .
H33 H 0.7736 0.1345 0.6208 0.163 Uiso 1 1 calc R . .
C34 C 0.5427(13) 0.0897(2) 0.5845(3) 0.160(3) Uani 1 1 d . . .
H34 H 0.4915 0.0881 0.6337 0.193 Uiso 1 1 calc R . .
C35 C 0.4452(10) 0.06369(17) 0.5195(3) 0.141(2) Uani 1 1 d . . .
H35 H 0.3301 0.0445 0.5251 0.17 Uiso 1 1 calc R . .
C36 C 0.5218(7) 0.06671(13) 0.4461(2) 0.0958(12) Uani 1 1 d . . .
H36 H 0.457 0.0496 0.4022 0.115 Uiso 1 1 calc R . .
C41 C 0.7684(4) 0.04201(9) 0.30017(15) 0.0559(6) Uani 1 1 d . . .
C42 C 0.6114(6) 0.02528(12) 0.2456(2) 0.0810(9) Uani 1 1 d . . .
H42 H 0.5015 0.0458 0.228 0.097 Uiso 1 1 calc R . .
C43 C 0.6135(7) -0.02191(14) 0.2160(2) 0.0961(11) Uani 1 1 d . . .
H43 H 0.5048 -0.0325 0.1789 0.115 Uiso 1 1 calc R . .
C44 C 0.7701(8) -0.05260(12) 0.2400(3) 0.0947(12) Uani 1 1 d . . .
H44 H 0.7705 -0.0842 0.2198 0.114 Uiso 1 1 calc R . .
C45 C 0.9263(8) -0.03682(13) 0.2938(3) 0.1068(13) Uani 1 1 d . . .
H45 H 1.0349 -0.0578 0.3111 0.128 Uiso 1 1 calc R . .
C46 C 0.9272(6) 0.01029(12) 0.3237(2) 0.0851(9) Uani 1 1 d . . .
H46 H 1.0373 0.0206 0.3604 0.102 Uiso 1 1 calc R . .
C51 C 0.2566(4) 0.38229(10) 0.53977(14) 0.0549(6) Uani 1 1 d . . .
C52 C 0.2938(5) 0.42779(11) 0.50876(18) 0.0695(8) Uani 1 1 d . . .
H52 H 0.3647 0.4301 0.4642 0.083 Uiso 1 1 calc R . .
C53 C 0.2266(6) 0.47019(12) 0.5434(2) 0.0907(11) Uani 1 1 d . . .
H53 H 0.2543 0.5005 0.5222 0.109 Uiso 1 1 calc R . .
C54 C 0.1209(7) 0.46733(16) 0.6078(3) 0.1032(13) Uani 1 1 d . . .
H54 H 0.0751 0.4956 0.6307 0.124 Uiso 1 1 calc R . .
C55 C 0.0817(6) 0.42238(16) 0.6393(2) 0.0977(12) Uani 1 1 d . . .
H55 H 0.0097 0.4205 0.6836 0.117 Uiso 1 1 calc R . .
C56 C 0.1479(5) 0.37982(13) 0.60582(17) 0.0716(8) Uani 1 1 d . . .
H56 H 0.1197 0.3497 0.6275 0.086 Uiso 1 1 calc R . .
C61 C 0.4909(4) 0.34108(8) 0.42083(13) 0.0476(5) Uani 1 1 d . . .
C62 C 0.4404(4) 0.32345(9) 0.34307(14) 0.0555(6) Uani 1 1 d . . .
H62 H 0.3169 0.3067 0.3296 0.067 Uiso 1 1 calc R . .
C63 C 0.5731(6) 0.33075(11) 0.28569(15) 0.0730(8) Uani 1 1 d . . .
H63 H 0.5396 0.3183 0.2343 0.088 Uiso 1 1 calc R . .
C64 C 0.7522(6) 0.35609(13) 0.30453(18) 0.0807(9) Uani 1 1 d . . .
H64 H 0.8411 0.3606 0.2659 0.097 Uiso 1 1 calc R . .
C65 C 0.8027(5) 0.37501(12) 0.37984(19) 0.0721(8) Uani 1 1 d . . .
H65 H 0.9234 0.393 0.3919 0.086 Uiso 1 1 calc R . .
C66 C 0.6734(4) 0.36721(10) 0.43799(16) 0.0598(6) Uani 1 1 d . . .
H66 H 0.7094 0.3797 0.4893 0.072 Uiso 1 1 calc R . .
Cl1 Cl 0.06121(13) 0.25862(4) 0.70264(5) 0.0915(3) Uani 1 1 d . . .
O1W O 0.1356(12) 0.1688(3) 0.6261(5) 0.154(3) Uani 0.5 1 d P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
P1 C31 1.831(3) . ?
P1 C41 1.839(3) . ?
P1 C12 1.850(3) . ?
P2 C51 1.833(3) . ?
P2 C61 1.834(2) . ?
P2 C22 1.849(2) . ?
N1 C2 1.332(3) . ?
N1 C5 1.373(3) . ?
N1 C11 1.478(3) . ?
C2 N3 1.333(3) . ?
C2 C6 1.473(3) . ?
N3 C4 1.382(3) . ?
N3 C21 1.475(3) . ?
C4 C5 1.339(3) . ?
C4 H4 0.93 . ?
C5 H5 0.93 . ?
C6 H601 0.96 . ?
C6 H602 0.96 . ?
C6 H603 0.96 . ?
C11 C12 1.522(4) . ?
C11 H111 0.97 . ?
C11 H112 0.97 . ?
C12 H121 0.97 . ?
C12 H122 0.97 . ?
C21 C22 1.517(4) . ?
C21 H211 0.97 . ?
C21 H212 0.97 . ?
C22 H221 0.97 . ?
C22 H222 0.97 . ?
C31 C36 1.379(5) . ?
C31 C32 1.385(4) . ?
C32 C33 1.383(6) . ?
C32 H32 0.93 . ?
C33 C34 1.344(9) . ?
C33 H33 0.93 . ?
C34 C35 1.390(9) . ?
C34 H34 0.93 . ?
C35 C36 1.390(5) . ?
C35 H35 0.93 . ?
C36 H36 0.93 . ?
C41 C42 1.366(4) . ?
C41 C46 1.371(4) . ?
C42 C43 1.386(4) . ?
C42 H42 0.93 . ?
C43 C44 1.345(5) . ?
C43 H43 0.93 . ?
C44 C45 1.345(6) . ?
C44 H44 0.93 . ?
C45 C46 1.386(5) . ?
C45 H45 0.93 . ?
C46 H46 0.93 . ?
C51 C52 1.384(4) . ?
C51 C56 1.391(4) . ?
C52 C53 1.394(4) . ?
C52 H52 0.93 . ?
C53 C54 1.357(5) . ?
C53 H53 0.93 . ?
C54 C55 1.377(6) . ?
C54 H54 0.93 . ?
C55 C56 1.387(4) . ?
C55 H55 0.93 . ?
C56 H56 0.93 . ?
C61 C66 1.387(4) . ?
C61 C62 1.394(3) . ?
C62 C63 1.387(4) . ?
C62 H62 0.93 . ?
C63 C64 1.361(5) . ?
C63 H63 0.93 . ?
C64 C65 1.370(4) . ?
C64 H64 0.93 . ?
C65 C66 1.384(4) . ?
C65 H65 0.93 . ?
C66 H66 0.93 . ?

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
C31 P1 C41 100.78(12) . . ?
C31 P1 C12 100.79(13) . . ?
C41 P1 C12 102.13(12) . . ?
C51 P2 C61 104.11(12) . . ?
C51 P2 C22 99.25(11) . . ?
C61 P2 C22 102.44(11) . . ?
C2 N1 C5 109.20(19) . . ?
C2 N1 C11 127.2(2) . . ?
C5 N1 C11 123.6(2) . . ?
N1 C2 N3 107.6(2) . . ?
N1 C2 C6 125.8(2) . . ?
N3 C2 C6 126.6(2) . . ?
C2 N3 C4 108.90(19) . . ?
C2 N3 C21 127.4(2) . . ?
C4 N3 C21 123.6(2) . . ?
C5 C4 N3 107.0(2) . . ?
C5 C4 H4 126.5 . . ?
N3 C4 H4 126.5 . . ?
C4 C5 N1 107.3(2) . . ?
C4 C5 H5 126.3 . . ?
N1 C5 H5 126.3 . . ?
C2 C6 H601 109.5 . . ?
C2 C6 H602 109.5 . . ?
H601 C6 H602 109.5 . . ?
C2 C6 H603 109.5 . . ?
H601 C6 H603 109.5 . . ?
H602 C6 H603 109.5 . . ?
N1 C11 C12 114.65(19) . . ?
N1 C11 H111 108.6 . . ?
C12 C11 H111 108.6 . . ?
N1 C11 H112 108.6 . . ?
C12 C11 H112 108.6 . . ?
H111 C11 H112 107.6 . . ?
C11 C12 P1 114.75(19) . . ?
C11 C12 H121 108.6 . . ?
P1 C12 H121 108.6 . . ?
C11 C12 H122 108.6 . . ?
P1 C12 H122 108.6 . . ?
H121 C12 H122 107.6 . . ?
N3 C21 C22 112.10(19) . . ?
N3 C21 H211 109.2 . . ?
C22 C21 H211 109.2 . . ?
N3 C21 H212 109.2 . . ?
C22 C21 H212 109.2 . . ?
H211 C21 H212 107.9 . . ?
C21 C22 P2 114.61(17) . . ?
C21 C22 H221 108.6 . . ?
P2 C22 H221 108.6 . . ?
C21 C22 H222 108.6 . . ?
P2 C22 H222 108.6 . . ?
H221 C22 H222 107.6 . . ?
C36 C31 C32 118.9(3) . . ?
C36 C31 P1 123.3(2) . . ?
C32 C31 P1 117.8(3) . . ?
C33 C32 C31 120.4(5) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 120.4(5) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 120.6(4) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C34 C35 C36 119.2(5) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
C31 C36 C35 120.4(4) . . ?
C31 C36 H36 119.8 . . ?
C35 C36 H36 119.8 . . ?
C42 C41 C46 117.1(3) . . ?
C42 C41 P1 126.5(2) . . ?
C46 C41 P1 116.3(2) . . ?
C41 C42 C43 120.9(3) . . ?
C41 C42 H42 119.5 . . ?
C43 C42 H42 119.5 . . ?
C44 C43 C42 121.1(4) . . ?
C44 C43 H43 119.4 . . ?
C42 C43 H43 119.4 . . ?
C43 C44 C45 118.9(3) . . ?
C43 C44 H44 120.6 . . ?
C45 C44 H44 120.6 . . ?
C44 C45 C46 120.8(4) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C41 C46 C45 121.1(4) . . ?
C41 C46 H46 119.4 . . ?
C45 C46 H46 119.4 . . ?
C52 C51 C56 118.3(3) . . ?
C52 C51 P2 124.7(2) . . ?
C56 C51 P2 116.7(2) . . ?
C51 C52 C53 121.0(3) . . ?
C51 C52 H52 119.5 . . ?
C53 C52 H52 119.5 . . ?
C54 C53 C52 120.1(4) . . ?
C54 C53 H53 119.9 . . ?
C52 C53 H53 119.9 . . ?
C53 C54 C55 119.7(3) . . ?
C53 C54 H54 120.2 . . ?
C55 C54 H54 120.2 . . ?
C54 C55 C56 121.0(3) . . ?
C54 C55 H55 119.5 . . ?
C56 C55 H55 119.5 . . ?
C55 C56 C51 119.9(3) . . ?
C55 C56 H56 120.1 . . ?
C51 C56 H56 120.1 . . ?
C66 C61 C62 118.0(2) . . ?
C66 C61 P2 124.98(18) . . ?
C62 C61 P2 116.83(19) . . ?
C63 C62 C61 120.5(3) . . ?
C63 C62 H62 119.8 . . ?
C61 C62 H62 119.8 . . ?
C64 C63 C62 120.1(3) . . ?
C64 C63 H63 119.9 . . ?
C62 C63 H63 119.9 . . ?
C63 C64 C65 120.6(3) . . ?
C63 C64 H64 119.7 . . ?
C65 C64 H64 119.7 . . ?
C64 C65 C66 119.8(3) . . ?
C64 C65 H65 120.1 . . ?
C66 C65 H65 120.1 . . ?
C65 C66 C61 120.9(3) . . ?
C65 C66 H66 119.5 . . ?
C61 C66 H66 119.5 . . ?

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
C5 N1 C2 N3 -1.3(3) . . . . ?
C11 N1 C2 N3 -178.3(2) . . . . ?
C5 N1 C2 C6 179.5(2) . . . . ?
C11 N1 C2 C6 2.5(4) . . . . ?
N1 C2 N3 C4 0.6(2) . . . . ?
C6 C2 N3 C4 179.9(2) . . . . ?
N1 C2 N3 C21 176.6(2) . . . . ?
C6 C2 N3 C21 -4.1(4) . . . . ?
C2 N3 C4 C5 0.2(3) . . . . ?
C21 N3 C4 C5 -175.9(2) . . . . ?
N3 C4 C5 N1 -1.0(3) . . . . ?
C2 N1 C5 C4 1.4(3) . . . . ?
C11 N1 C5 C4 178.5(2) . . . . ?
C2 N1 C11 C12 -69.9(3) . . . . ?
C5 N1 C11 C12 113.5(3) . . . . ?
N1 C11 C12 P1 -47.4(3) . . . . ?
C31 P1 C12 C11 92.4(2) . . . . ?
C41 P1 C12 C11 -163.97(18) . . . . ?
C2 N3 C21 C22 -105.9(3) . . . . ?
C4 N3 C21 C22 69.5(3) . . . . ?
N3 C21 C22 P2 53.6(3) . . . . ?
C51 P2 C22 C21 167.08(19) . . . . ?
C61 P2 C22 C21 -86.1(2) . . . . ?
C41 P1 C31 C36 -41.0(3) . . . . ?
C12 P1 C31 C36 63.8(3) . . . . ?
C41 P1 C31 C32 141.7(2) . . . . ?
C12 P1 C31 C32 -113.6(2) . . . . ?
C36 C31 C32 C33 -2.4(5) . . . . ?
P1 C31 C32 C33 175.1(3) . . . . ?
C31 C32 C33 C34 2.1(6) . . . . ?
C32 C33 C34 C35 -0.5(8) . . . . ?
C33 C34 C35 C36 -0.7(8) . . . . ?
C32 C31 C36 C35 1.1(5) . . . . ?
P1 C31 C36 C35 -176.2(3) . . . . ?
C34 C35 C36 C31 0.4(7) . . . . ?
C31 P1 C41 C42 98.1(3) . . . . ?
C12 P1 C41 C42 -5.6(3) . . . . ?
C31 P1 C41 C46 -84.8(2) . . . . ?
C12 P1 C41 C46 171.6(2) . . . . ?
C46 C41 C42 C43 0.4(5) . . . . ?
P1 C41 C42 C43 177.5(3) . . . . ?
C41 C42 C43 C44 -0.1(6) . . . . ?
C42 C43 C44 C45 0.1(6) . . . . ?
C43 C44 C45 C46 -0.4(6) . . . . ?
C42 C41 C46 C45 -0.6(5) . . . . ?
P1 C41 C46 C45 -178.0(3) . . . . ?
C44 C45 C46 C41 0.7(6) . . . . ?
C61 P2 C51 C52 14.3(3) . . . . ?
C22 P2 C51 C52 119.7(3) . . . . ?
C61 P2 C51 C56 -171.9(2) . . . . ?
C22 P2 C51 C56 -66.4(2) . . . . ?
C56 C51 C52 C53 0.8(4) . . . . ?
P2 C51 C52 C53 174.6(2) . . . . ?
C51 C52 C53 C54 -0.8(5) . . . . ?
C52 C53 C54 C55 0.5(6) . . . . ?
C53 C54 C55 C56 -0.3(6) . . . . ?
C54 C55 C56 C51 0.4(5) . . . . ?
C52 C51 C56 C55 -0.6(4) . . . . ?
P2 C51 C56 C55 -174.9(3) . . . . ?
C51 P2 C61 C66 55.5(2) . . . . ?
C22 P2 C61 C66 -47.5(2) . . . . ?
C51 P2 C61 C62 -128.88(19) . . . . ?
C22 P2 C61 C62 128.1(2) . . . . ?
C66 C61 C62 C63 2.0(4) . . . . ?
P2 C61 C62 C63 -173.9(2) . . . . ?
C61 C62 C63 C64 -1.3(4) . . . . ?
C62 C63 C64 C65 -0.6(5) . . . . ?
C63 C64 C65 C66 1.8(5) . . . . ?
C64 C65 C66 C61 -1.1(4) . . . . ?
C62 C61 C66 C65 -0.8(4) . . . . ?
P2 C61 C66 C65 174.8(2) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1402757'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_date             2014-03-01T12:24:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C40 H44 Ir N2 P2, F6 P, C H2 Cl2'
_chemical_formula_sum            'C41 H46 Cl2 F6 Ir N2 P3'
_chemical_formula_weight         1036.81

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.973(2)
_cell_length_b                   11.5843(14)
_cell_length_c                   19.988(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.642(2)
_cell_angle_gamma                90
_cell_volume                     4102.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9415
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      28.23

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prisms
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.45
_exptl_crystal_density_diffrn    1.679
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2064
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.562
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.133
_exptl_absorpt_correction_T_max  0.201

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.089
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_number            47105
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         28.59
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.931
_reflns_number_total             9765
_reflns_number_gt                6799
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0296P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9765
_refine_ls_number_parameters     496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0732
_refine_ls_wR_factor_gt          0.0658
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.332
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.097

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
F F 0.0171 0.0103 '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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.225524(8) 0.447345(12) 0.473339(7) 0.03266(5) Uani 1 1 d . . .
P1 P 0.25707(5) 0.53557(8) 0.37348(5) 0.0345(2) Uani 1 1 d . . .
N1 N 0.42213(17) 0.5523(3) 0.44195(16) 0.0421(8) Uani 1 1 d . . .
P2 P 0.21726(5) 0.59787(8) 0.55095(5) 0.0315(2) Uani 1 1 d . . .
C2 C 0.39065(19) 0.5284(3) 0.49704(19) 0.0376(9) Uani 1 1 d . . .
N3 N 0.40764(16) 0.6166(3) 0.54017(16) 0.0404(8) Uani 1 1 d . . .
C4 C 0.4504(2) 0.6973(4) 0.5123(2) 0.0507(11) Uani 1 1 d . . .
H4 H 0.4694 0.7663 0.532 0.061 Uiso 1 1 calc R . .
C5 C 0.4591(2) 0.6560(4) 0.4508(2) 0.0502(11) Uani 1 1 d . . .
H5 H 0.4854 0.6915 0.4201 0.06 Uiso 1 1 calc R . .
C11 C 0.4147(2) 0.4799(4) 0.3807(2) 0.0545(12) Uani 1 1 d . . .
H111 H 0.4401 0.4072 0.3929 0.065 Uiso 1 1 calc R . .
H112 H 0.4412 0.5178 0.3483 0.065 Uiso 1 1 calc R . .
C12 C 0.3343(2) 0.4535(3) 0.3451(2) 0.0473(10) Uani 1 1 d . . .
H121 H 0.3248 0.372 0.3508 0.057 Uiso 1 1 calc R . .
H122 H 0.3318 0.4672 0.2969 0.057 Uiso 1 1 calc R . .
C21 C 0.3447(2) 0.4297(3) 0.5067(2) 0.0411(9) Uani 1 1 d . . .
H211 H 0.3532 0.411 0.5547 0.049 Uiso 1 1 calc R . .
H212 H 0.3622 0.3646 0.4831 0.049 Uiso 1 1 calc R . .
C31 C 0.3794(2) 0.6292(4) 0.60402(19) 0.0463(10) Uani 1 1 d . . .
H311 H 0.4137 0.6775 0.6346 0.056 Uiso 1 1 calc R . .
H312 H 0.3776 0.554 0.6251 0.056 Uiso 1 1 calc R . .
C32 C 0.3006(2) 0.6831(3) 0.59289(19) 0.0414(9) Uani 1 1 d . . .
H321 H 0.3028 0.7528 0.5664 0.05 Uiso 1 1 calc R . .
H322 H 0.2903 0.707 0.637 0.05 Uiso 1 1 calc R . .
C41 C 0.2898(2) 0.6841(3) 0.36564(18) 0.0380(9) Uani 1 1 d . . .
C42 C 0.2837(2) 0.7660(3) 0.4143(2) 0.0427(9) Uani 1 1 d . . .
H42 H 0.2627 0.7447 0.4519 0.051 Uiso 1 1 calc R . .
C43 C 0.3073(3) 0.8778(4) 0.4095(2) 0.0581(12) Uani 1 1 d . . .
H43 H 0.3009 0.9315 0.4427 0.07 Uiso 1 1 calc R . .
C44 C 0.3403(3) 0.9096(4) 0.3554(3) 0.0725(15) Uani 1 1 d . . .
H44 H 0.3573 0.9849 0.352 0.087 Uiso 1 1 calc R . .
C45 C 0.3484(3) 0.8298(4) 0.3060(3) 0.0723(15) Uani 1 1 d . . .
H45 H 0.3716 0.8513 0.2696 0.087 Uiso 1 1 calc R . .
C46 C 0.3224(3) 0.7179(4) 0.3101(2) 0.0561(12) Uani 1 1 d . . .
H46 H 0.3265 0.6653 0.2758 0.067 Uiso 1 1 calc R . .
C51 C 0.1838(2) 0.5303(4) 0.29793(19) 0.0435(10) Uani 1 1 d . . .
C52 C 0.1687(3) 0.4321(4) 0.2577(2) 0.0607(12) Uani 1 1 d . . .
H52 H 0.2008 0.3688 0.2653 0.073 Uiso 1 1 calc R . .
C53 C 0.1063(3) 0.4279(6) 0.2067(2) 0.0810(18) Uani 1 1 d . . .
H53 H 0.0963 0.3612 0.1808 0.097 Uiso 1 1 calc R . .
C54 C 0.0594(3) 0.5210(6) 0.1941(2) 0.0818(18) Uani 1 1 d . . .
H54 H 0.0171 0.5169 0.1603 0.098 Uiso 1 1 calc R . .
C55 C 0.0743(3) 0.6188(5) 0.2304(2) 0.0708(15) Uani 1 1 d . . .
H55 H 0.043 0.6828 0.2209 0.085 Uiso 1 1 calc R . .
C56 C 0.1364(2) 0.6240(4) 0.2822(2) 0.0535(11) Uani 1 1 d . . .
H56 H 0.1463 0.692 0.3067 0.064 Uiso 1 1 calc R . .
C61 C 0.1808(2) 0.5499(3) 0.62695(18) 0.0376(8) Uani 1 1 d . . .
C62 C 0.2244(2) 0.4744(4) 0.6707(2) 0.0575(12) Uani 1 1 d . . .
H62 H 0.271 0.4504 0.6614 0.069 Uiso 1 1 calc R . .
C63 C 0.1994(3) 0.4344(5) 0.7279(3) 0.0784(17) Uani 1 1 d . . .
H63 H 0.2301 0.3864 0.758 0.094 Uiso 1 1 calc R . .
C64 C 0.1294(3) 0.4650(5) 0.7408(3) 0.0820(18) Uani 1 1 d . . .
H64 H 0.1124 0.437 0.7792 0.098 Uiso 1 1 calc R . .
C65 C 0.0847(3) 0.5371(4) 0.6967(3) 0.0741(16) Uani 1 1 d . . .
H65 H 0.0369 0.5568 0.7048 0.089 Uiso 1 1 calc R . .
C66 C 0.1101(2) 0.5805(4) 0.6406(2) 0.0536(12) Uani 1 1 d . . .
H66 H 0.0798 0.6308 0.6117 0.064 Uiso 1 1 calc R . .
C71 C 0.15475(19) 0.7204(3) 0.52148(18) 0.0340(8) Uani 1 1 d . . .
C72 C 0.1499(2) 0.8170(3) 0.5620(2) 0.0469(10) Uani 1 1 d . . .
H72 H 0.1733 0.8161 0.6072 0.056 Uiso 1 1 calc R . .
C73 C 0.1108(3) 0.9141(4) 0.5359(2) 0.0549(12) Uani 1 1 d . . .
H73 H 0.1092 0.9789 0.563 0.066 Uiso 1 1 calc R . .
C74 C 0.0743(3) 0.9149(4) 0.4696(2) 0.0579(12) Uani 1 1 d . . .
H74 H 0.0482 0.9804 0.452 0.069 Uiso 1 1 calc R . .
C75 C 0.0762(2) 0.8193(4) 0.4294(2) 0.0484(10) Uani 1 1 d . . .
H75 H 0.0506 0.8192 0.3849 0.058 Uiso 1 1 calc R . .
C76 C 0.11658(19) 0.7233(3) 0.45540(19) 0.0392(9) Uani 1 1 d . . .
H76 H 0.1181 0.659 0.4278 0.047 Uiso 1 1 calc R . .
C81 C 0.1101(2) 0.4113(4) 0.4154(2) 0.0485(10) Uani 1 1 d . . .
H81 H 0.0902 0.4725 0.3835 0.058 Uiso 1 1 calc R . .
C82 C 0.1027(2) 0.4336(3) 0.4823(2) 0.0450(10) Uani 1 1 d . . .
H82 H 0.0787 0.5077 0.4889 0.054 Uiso 1 1 calc R . .
C83 C 0.0875(3) 0.3405(4) 0.5307(2) 0.0624(13) Uani 1 1 d . . .
H831 H 0.0403 0.3028 0.5123 0.075 Uiso 1 1 calc R . .
H832 H 0.0813 0.3762 0.5733 0.075 Uiso 1 1 calc R . .
C84 C 0.1484(3) 0.2504(4) 0.5446(3) 0.0840(17) Uani 1 1 d . . .
H841 H 0.13 0.1796 0.5216 0.101 Uiso 1 1 calc R . .
H842 H 0.1582 0.2346 0.5929 0.101 Uiso 1 1 calc R . .
C85 C 0.2223(3) 0.2841(3) 0.5220(3) 0.0578(12) Uani 1 1 d . . .
H85 H 0.2673 0.2671 0.5555 0.069 Uiso 1 1 calc R . .
C86 C 0.2326(3) 0.2682(3) 0.4524(2) 0.0577(12) Uani 1 1 d . . .
H86 H 0.2838 0.2432 0.4482 0.069 Uiso 1 1 calc R . .
C87 C 0.1726(3) 0.2173(4) 0.3987(3) 0.0791(16) Uani 1 1 d . . .
H871 H 0.1598 0.1407 0.4127 0.095 Uiso 1 1 calc R . .
H872 H 0.1925 0.2096 0.3567 0.095 Uiso 1 1 calc R . .
C88 C 0.1011(3) 0.2907(4) 0.3856(2) 0.0648(13) Uani 1 1 d . . .
H881 H 0.0846 0.2968 0.337 0.078 Uiso 1 1 calc R . .
H882 H 0.0617 0.2512 0.4045 0.078 Uiso 1 1 calc R . .
Cl91 Cl 0.31000(14) 0.49228(19) 0.12252(15) 0.1570(9) Uani 1 1 d . . .
C92 C 0.3999(4) 0.4412(5) 0.1225(3) 0.111(2) Uani 1 1 d . . .
H921 H 0.4353 0.4898 0.1518 0.133 Uiso 1 1 calc R . .
H922 H 0.4037 0.364 0.1415 0.133 Uiso 1 1 calc R . .
Cl93 Cl 0.42523(16) 0.4373(2) 0.04371(13) 0.1697(10) Uani 1 1 d . . .
P100 P 0.55294(7) 0.68159(10) 0.24191(6) 0.0548(3) Uani 1 1 d . . .
F101 F 0.5500(3) 0.6766(3) 0.16333(16) 0.1386(16) Uani 1 1 d . . .
F102 F 0.4656(2) 0.6555(4) 0.2292(3) 0.1427(16) Uani 1 1 d . . .
F103 F 0.5366(2) 0.8147(2) 0.23587(16) 0.0972(10) Uani 1 1 d . . .
F104 F 0.63681(19) 0.7088(4) 0.2536(3) 0.1533(19) Uani 1 1 d . . .
F105 F 0.5695(2) 0.5494(2) 0.2478(2) 0.1171(14) Uani 1 1 d . . .
F106 F 0.5515(3) 0.6855(3) 0.31996(16) 0.1230(14) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C86 2.126(4) . ?
Ir1 C85 2.132(4) . ?
Ir1 C21 2.144(4) . ?
Ir1 C81 2.239(4) . ?
Ir1 C82 2.250(4) . ?
Ir1 P2 2.3550(10) . ?
Ir1 P1 2.3935(10) . ?
P1 C51 1.831(4) . ?
P1 C41 1.833(4) . ?
P1 C12 1.847(4) . ?
N1 C2 1.348(5) . ?
N1 C5 1.370(5) . ?
N1 C11 1.472(5) . ?
P2 C61 1.839(4) . ?
P2 C71 1.844(4) . ?
P2 C32 1.871(4) . ?
C2 N3 1.339(5) . ?
C2 C21 1.442(5) . ?
N3 C4 1.385(5) . ?
N3 C31 1.458(5) . ?
C4 C5 1.353(6) . ?
C4 H4 0.93 . ?
C5 H5 0.93 . ?
C11 C12 1.531(6) . ?
C11 H111 0.97 . ?
C11 H112 0.97 . ?
C12 H121 0.97 . ?
C12 H122 0.97 . ?
C21 H211 0.97 . ?
C21 H212 0.97 . ?
C31 C32 1.530(5) . ?
C31 H311 0.97 . ?
C31 H312 0.97 . ?
C32 H321 0.97 . ?
C32 H322 0.97 . ?
C41 C42 1.377(5) . ?
C41 C46 1.395(5) . ?
C42 C43 1.371(5) . ?
C42 H42 0.93 . ?
C43 C44 1.369(6) . ?
C43 H43 0.93 . ?
C44 C45 1.378(7) . ?
C44 H44 0.93 . ?
C45 C46 1.385(6) . ?
C45 H45 0.93 . ?
C46 H46 0.93 . ?
C51 C56 1.383(6) . ?
C51 C52 1.393(6) . ?
C52 C53 1.385(7) . ?
C52 H52 0.93 . ?
C53 C54 1.366(8) . ?
C53 H53 0.93 . ?
C54 C55 1.349(8) . ?
C54 H54 0.93 . ?
C55 C56 1.390(6) . ?
C55 H55 0.93 . ?
C56 H56 0.93 . ?
C61 C62 1.384(5) . ?
C61 C66 1.389(5) . ?
C62 C63 1.377(6) . ?
C62 H62 0.93 . ?
C63 C64 1.372(7) . ?
C63 H63 0.93 . ?
C64 C65 1.373(7) . ?
C64 H64 0.93 . ?
C65 C66 1.374(6) . ?
C65 H65 0.93 . ?
C66 H66 0.93 . ?
C71 C76 1.383(5) . ?
C71 C72 1.393(5) . ?
C72 C73 1.382(5) . ?
C72 H72 0.93 . ?
C73 C74 1.377(6) . ?
C73 H73 0.93 . ?
C74 C75 1.372(6) . ?
C74 H74 0.93 . ?
C75 C76 1.381(5) . ?
C75 H75 0.93 . ?
C76 H76 0.93 . ?
C81 C82 1.390(6) . ?
C81 C88 1.517(6) . ?
C81 H81 0.98 . ?
C82 C83 1.504(6) . ?
C82 H82 0.98 . ?
C83 C84 1.504(6) . ?
C83 H831 0.97 . ?
C83 H832 0.97 . ?
C84 C85 1.524(6) . ?
C84 H841 0.97 . ?
C84 H842 0.97 . ?
C85 C86 1.446(6) . ?
C85 H85 0.98 . ?
C86 C87 1.508(6) . ?
C86 H86 0.98 . ?
C87 C88 1.525(7) . ?
C87 H871 0.97 . ?
C87 H872 0.97 . ?
C88 H881 0.97 . ?
C88 H882 0.97 . ?
Cl91 C92 1.720(7) . ?
C92 Cl93 1.712(7) . ?
C92 H921 0.97 . ?
C92 H922 0.97 . ?
P100 F104 1.519(4) . ?
P100 F105 1.561(3) . ?
P100 F101 1.564(3) . ?
P100 F106 1.565(3) . ?
P100 F103 1.570(3) . ?
P100 F102 1.576(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
C86 Ir1 C85 39.72(17) . . ?
C86 Ir1 C21 83.01(16) . . ?
C85 Ir1 C21 82.87(16) . . ?
C86 Ir1 C81 78.30(17) . . ?
C85 Ir1 C81 88.68(17) . . ?
C21 Ir1 C81 159.05(15) . . ?
C86 Ir1 C82 92.22(16) . . ?
C85 Ir1 C82 78.40(16) . . ?
C21 Ir1 C82 155.66(15) . . ?
C81 Ir1 C82 36.06(15) . . ?
C86 Ir1 P2 149.94(13) . . ?
C85 Ir1 P2 110.30(14) . . ?
C21 Ir1 P2 92.04(11) . . ?
C81 Ir1 P2 108.88(11) . . ?
C82 Ir1 P2 80.17(11) . . ?
C86 Ir1 P1 102.82(13) . . ?
C85 Ir1 P1 141.95(14) . . ?
C21 Ir1 P1 86.33(11) . . ?
C81 Ir1 P1 88.64(12) . . ?
C82 Ir1 P1 117.96(11) . . ?
P2 Ir1 P1 106.44(3) . . ?
C51 P1 C41 99.07(18) . . ?
C51 P1 C12 101.72(19) . . ?
C41 P1 C12 100.84(18) . . ?
C51 P1 Ir1 115.80(13) . . ?
C41 P1 Ir1 126.61(12) . . ?
C12 P1 Ir1 109.34(14) . . ?
C2 N1 C5 109.6(3) . . ?
C2 N1 C11 124.8(3) . . ?
C5 N1 C11 125.5(3) . . ?
C61 P2 C71 102.37(16) . . ?
C61 P2 C32 99.14(17) . . ?
C71 P2 C32 97.82(17) . . ?
C61 P2 Ir1 113.00(12) . . ?
C71 P2 Ir1 117.49(12) . . ?
C32 P2 Ir1 123.50(12) . . ?
N3 C2 N1 106.7(3) . . ?
N3 C2 C21 126.4(4) . . ?
N1 C2 C21 126.9(4) . . ?
C2 N3 C4 109.8(3) . . ?
C2 N3 C31 124.4(3) . . ?
C4 N3 C31 125.6(3) . . ?
C5 C4 N3 106.5(4) . . ?
C5 C4 H4 126.8 . . ?
N3 C4 H4 126.8 . . ?
C4 C5 N1 107.4(4) . . ?
C4 C5 H5 126.3 . . ?
N1 C5 H5 126.3 . . ?
N1 C11 C12 116.5(3) . . ?
N1 C11 H111 108.2 . . ?
C12 C11 H111 108.2 . . ?
N1 C11 H112 108.2 . . ?
C12 C11 H112 108.2 . . ?
H111 C11 H112 107.3 . . ?
C11 C12 P1 117.0(3) . . ?
C11 C12 H121 108 . . ?
P1 C12 H121 108 . . ?
C11 C12 H122 108 . . ?
P1 C12 H122 108 . . ?
H121 C12 H122 107.3 . . ?
C2 C21 Ir1 116.6(2) . . ?
C2 C21 H211 108.1 . . ?
Ir1 C21 H211 108.1 . . ?
C2 C21 H212 108.1 . . ?
Ir1 C21 H212 108.1 . . ?
H211 C21 H212 107.3 . . ?
N3 C31 C32 111.3(3) . . ?
N3 C31 H311 109.4 . . ?
C32 C31 H311 109.4 . . ?
N3 C31 H312 109.4 . . ?
C32 C31 H312 109.4 . . ?
H311 C31 H312 108 . . ?
C31 C32 P2 120.1(3) . . ?
C31 C32 H321 107.3 . . ?
P2 C32 H321 107.3 . . ?
C31 C32 H322 107.3 . . ?
P2 C32 H322 107.3 . . ?
H321 C32 H322 106.9 . . ?
C42 C41 C46 117.5(4) . . ?
C42 C41 P1 121.5(3) . . ?
C46 C41 P1 121.0(3) . . ?
C43 C42 C41 122.7(4) . . ?
C43 C42 H42 118.7 . . ?
C41 C42 H42 118.7 . . ?
C44 C43 C42 119.3(4) . . ?
C44 C43 H43 120.3 . . ?
C42 C43 H43 120.3 . . ?
C43 C44 C45 119.9(5) . . ?
C43 C44 H44 120.1 . . ?
C45 C44 H44 120.1 . . ?
C44 C45 C46 120.5(4) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C45 C46 C41 120.1(4) . . ?
C45 C46 H46 120 . . ?
C41 C46 H46 120 . . ?
C56 C51 C52 117.1(4) . . ?
C56 C51 P1 119.5(3) . . ?
C52 C51 P1 123.1(3) . . ?
C53 C52 C51 120.6(5) . . ?
C53 C52 H52 119.7 . . ?
C51 C52 H52 119.7 . . ?
C54 C53 C52 120.5(5) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
C55 C54 C53 120.2(5) . . ?
C55 C54 H54 119.9 . . ?
C53 C54 H54 119.9 . . ?
C54 C55 C56 119.9(5) . . ?
C54 C55 H55 120 . . ?
C56 C55 H55 120 . . ?
C51 C56 C55 121.6(5) . . ?
C51 C56 H56 119.2 . . ?
C55 C56 H56 119.2 . . ?
C62 C61 C66 118.5(4) . . ?
C62 C61 P2 118.1(3) . . ?
C66 C61 P2 123.3(3) . . ?
C63 C62 C61 120.6(4) . . ?
C63 C62 H62 119.7 . . ?
C61 C62 H62 119.7 . . ?
C64 C63 C62 120.4(4) . . ?
C64 C63 H63 119.8 . . ?
C62 C63 H63 119.8 . . ?
C63 C64 C65 119.5(4) . . ?
C63 C64 H64 120.2 . . ?
C65 C64 H64 120.2 . . ?
C64 C65 C66 120.6(4) . . ?
C64 C65 H65 119.7 . . ?
C66 C65 H65 119.7 . . ?
C65 C66 C61 120.4(4) . . ?
C65 C66 H66 119.8 . . ?
C61 C66 H66 119.8 . . ?
C76 C71 C72 117.8(3) . . ?
C76 C71 P2 120.1(3) . . ?
C72 C71 P2 121.8(3) . . ?
C73 C72 C71 120.8(4) . . ?
C73 C72 H72 119.6 . . ?
C71 C72 H72 119.6 . . ?
C74 C73 C72 120.0(4) . . ?
C74 C73 H73 120 . . ?
C72 C73 H73 120 . . ?
C75 C74 C73 120.2(4) . . ?
C75 C74 H74 119.9 . . ?
C73 C74 H74 119.9 . . ?
C74 C75 C76 119.5(4) . . ?
C74 C75 H75 120.2 . . ?
C76 C75 H75 120.2 . . ?
C75 C76 C71 121.6(4) . . ?
C75 C76 H76 119.2 . . ?
C71 C76 H76 119.2 . . ?
C82 C81 C88 121.8(4) . . ?
C82 C81 Ir1 72.4(2) . . ?
C88 C81 Ir1 113.8(3) . . ?
C82 C81 H81 114.1 . . ?
C88 C81 H81 114.1 . . ?
Ir1 C81 H81 114.1 . . ?
C81 C82 C83 122.9(4) . . ?
C81 C82 Ir1 71.5(2) . . ?
C83 C82 Ir1 112.8(3) . . ?
C81 C82 H82 114.1 . . ?
C83 C82 H82 114.1 . . ?
Ir1 C82 H82 114.1 . . ?
C82 C83 C84 114.3(4) . . ?
C82 C83 H831 108.7 . . ?
C84 C83 H831 108.7 . . ?
C82 C83 H832 108.7 . . ?
C84 C83 H832 108.7 . . ?
H831 C83 H832 107.6 . . ?
C83 C84 C85 114.2(4) . . ?
C83 C84 H841 108.7 . . ?
C85 C84 H841 108.7 . . ?
C83 C84 H842 108.7 . . ?
C85 C84 H842 108.7 . . ?
H841 C84 H842 107.6 . . ?
C86 C85 C84 120.8(5) . . ?
C86 C85 Ir1 69.9(2) . . ?
C84 C85 Ir1 117.0(3) . . ?
C86 C85 H85 114 . . ?
C84 C85 H85 114 . . ?
Ir1 C85 H85 114 . . ?
C85 C86 C87 122.8(4) . . ?
C85 C86 Ir1 70.4(2) . . ?
C87 C86 Ir1 117.5(3) . . ?
C85 C86 H86 113.2 . . ?
C87 C86 H86 113.2 . . ?
Ir1 C86 H86 113.2 . . ?
C86 C87 C88 112.7(4) . . ?
C86 C87 H871 109 . . ?
C88 C87 H871 109 . . ?
C86 C87 H872 109 . . ?
C88 C87 H872 109 . . ?
H871 C87 H872 107.8 . . ?
C81 C88 C87 114.5(4) . . ?
C81 C88 H881 108.6 . . ?
C87 C88 H881 108.6 . . ?
C81 C88 H882 108.6 . . ?
C87 C88 H882 108.6 . . ?
H881 C88 H882 107.6 . . ?
Cl93 C92 Cl91 113.8(4) . . ?
Cl93 C92 H921 108.8 . . ?
Cl91 C92 H921 108.8 . . ?
Cl93 C92 H922 108.8 . . ?
Cl91 C92 H922 108.8 . . ?
H921 C92 H922 107.7 . . ?
F104 P100 F105 91.1(2) . . ?
F104 P100 F101 91.7(3) . . ?
F105 P100 F101 90.8(2) . . ?
F104 P100 F106 91.2(3) . . ?
F105 P100 F106 89.3(2) . . ?
F101 P100 F106 177.1(3) . . ?
F104 P100 F103 88.6(2) . . ?
F105 P100 F103 179.7(2) . . ?
F101 P100 F103 89.12(19) . . ?
F106 P100 F103 90.81(18) . . ?
F104 P100 F102 179.0(2) . . ?
F105 P100 F102 89.8(2) . . ?
F101 P100 F102 88.0(3) . . ?
F106 P100 F102 89.1(2) . . ?
F103 P100 F102 90.5(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
C86 Ir1 P1 C51 74.6(2) . . . . ?
C85 Ir1 P1 C51 83.1(3) . . . . ?
C21 Ir1 P1 C51 156.58(18) . . . . ?
C81 Ir1 P1 C51 -3.07(19) . . . . ?
C82 Ir1 P1 C51 -24.94(19) . . . . ?
P2 Ir1 P1 C51 -112.37(15) . . . . ?
C86 Ir1 P1 C41 -160.1(2) . . . . ?
C85 Ir1 P1 C41 -151.7(2) . . . . ?
C21 Ir1 P1 C41 -78.16(18) . . . . ?
C81 Ir1 P1 C41 122.20(18) . . . . ?
C82 Ir1 P1 C41 100.33(19) . . . . ?
P2 Ir1 P1 C41 12.89(15) . . . . ?
C86 Ir1 P1 C12 -39.53(19) . . . . ?
C85 Ir1 P1 C12 -31.1(3) . . . . ?
C21 Ir1 P1 C12 42.44(18) . . . . ?
C81 Ir1 P1 C12 -117.20(18) . . . . ?
C82 Ir1 P1 C12 -139.07(19) . . . . ?
P2 Ir1 P1 C12 133.49(15) . . . . ?
C86 Ir1 P2 C61 -21.5(3) . . . . ?
C85 Ir1 P2 C61 -17.90(19) . . . . ?
C21 Ir1 P2 C61 -101.05(17) . . . . ?
C81 Ir1 P2 C61 77.88(18) . . . . ?
C82 Ir1 P2 C61 55.74(17) . . . . ?
P1 Ir1 P2 C61 172.17(13) . . . . ?
C86 Ir1 P2 C71 -140.4(3) . . . . ?
C85 Ir1 P2 C71 -136.80(18) . . . . ?
C21 Ir1 P2 C71 140.05(16) . . . . ?
C81 Ir1 P2 C71 -41.02(17) . . . . ?
C82 Ir1 P2 C71 -63.15(16) . . . . ?
P1 Ir1 P2 C71 53.27(13) . . . . ?
C86 Ir1 P2 C32 97.7(3) . . . . ?
C85 Ir1 P2 C32 101.3(2) . . . . ?
C21 Ir1 P2 C32 18.16(19) . . . . ?
C81 Ir1 P2 C32 -162.91(19) . . . . ?
C82 Ir1 P2 C32 174.95(19) . . . . ?
P1 Ir1 P2 C32 -68.62(16) . . . . ?
C5 N1 C2 N3 0.1(4) . . . . ?
C11 N1 C2 N3 -177.4(3) . . . . ?
C5 N1 C2 C21 177.6(4) . . . . ?
C11 N1 C2 C21 0.1(6) . . . . ?
N1 C2 N3 C4 -0.1(4) . . . . ?
C21 C2 N3 C4 -177.6(3) . . . . ?
N1 C2 N3 C31 175.0(3) . . . . ?
C21 C2 N3 C31 -2.4(6) . . . . ?
C2 N3 C4 C5 0.0(4) . . . . ?
C31 N3 C4 C5 -175.0(3) . . . . ?
N3 C4 C5 N1 0.0(4) . . . . ?
C2 N1 C5 C4 -0.1(4) . . . . ?
C11 N1 C5 C4 177.4(4) . . . . ?
C2 N1 C11 C12 56.1(5) . . . . ?
C5 N1 C11 C12 -121.0(4) . . . . ?
N1 C11 C12 P1 10.7(5) . . . . ?
C51 P1 C12 C11 154.9(3) . . . . ?
C41 P1 C12 C11 53.1(4) . . . . ?
Ir1 P1 C12 C11 -82.1(3) . . . . ?
N3 C2 C21 Ir1 87.6(4) . . . . ?
N1 C2 C21 Ir1 -89.3(4) . . . . ?
C86 Ir1 C21 C2 147.4(3) . . . . ?
C85 Ir1 C21 C2 -172.6(3) . . . . ?
C81 Ir1 C21 C2 120.4(4) . . . . ?
C82 Ir1 C21 C2 -132.8(4) . . . . ?
P2 Ir1 C21 C2 -62.4(3) . . . . ?
P1 Ir1 C21 C2 43.9(3) . . . . ?
C2 N3 C31 C32 -83.1(5) . . . . ?
C4 N3 C31 C32 91.3(4) . . . . ?
N3 C31 C32 P2 71.4(4) . . . . ?
C61 P2 C32 C31 98.5(3) . . . . ?
C71 P2 C32 C31 -157.5(3) . . . . ?
Ir1 P2 C32 C31 -27.0(4) . . . . ?
C51 P1 C41 C42 117.7(3) . . . . ?
C12 P1 C41 C42 -138.4(3) . . . . ?
Ir1 P1 C41 C42 -14.2(4) . . . . ?
C51 P1 C41 C46 -62.6(4) . . . . ?
C12 P1 C41 C46 41.2(4) . . . . ?
Ir1 P1 C41 C46 165.5(3) . . . . ?
C46 C41 C42 C43 0.8(6) . . . . ?
P1 C41 C42 C43 -179.6(3) . . . . ?
C41 C42 C43 C44 -1.9(7) . . . . ?
C42 C43 C44 C45 1.1(8) . . . . ?
C43 C44 C45 C46 0.9(8) . . . . ?
C44 C45 C46 C41 -2.1(8) . . . . ?
C42 C41 C46 C45 1.3(6) . . . . ?
P1 C41 C46 C45 -178.4(4) . . . . ?
C41 P1 C51 C56 -42.0(4) . . . . ?
C12 P1 C51 C56 -145.1(3) . . . . ?
Ir1 P1 C51 C56 96.4(3) . . . . ?
C41 P1 C51 C52 143.5(4) . . . . ?
C12 P1 C51 C52 40.4(4) . . . . ?
Ir1 P1 C51 C52 -78.0(4) . . . . ?
C56 C51 C52 C53 -3.3(6) . . . . ?
P1 C51 C52 C53 171.3(4) . . . . ?
C51 C52 C53 C54 1.3(8) . . . . ?
C52 C53 C54 C55 1.3(8) . . . . ?
C53 C54 C55 C56 -1.7(8) . . . . ?
C52 C51 C56 C55 2.9(6) . . . . ?
P1 C51 C56 C55 -171.9(3) . . . . ?
C54 C55 C56 C51 -0.4(7) . . . . ?
C71 P2 C61 C62 -166.4(3) . . . . ?
C32 P2 C61 C62 -66.2(4) . . . . ?
Ir1 P2 C61 C62 66.3(4) . . . . ?
C71 P2 C61 C66 17.2(4) . . . . ?
C32 P2 C61 C66 117.3(4) . . . . ?
Ir1 P2 C61 C66 -110.2(4) . . . . ?
C66 C61 C62 C63 -2.5(7) . . . . ?
P2 C61 C62 C63 -179.1(4) . . . . ?
C61 C62 C63 C64 2.8(9) . . . . ?
C62 C63 C64 C65 -0.9(10) . . . . ?
C63 C64 C65 C66 -1.2(9) . . . . ?
C64 C65 C66 C61 1.5(8) . . . . ?
C62 C61 C66 C65 0.4(7) . . . . ?
P2 C61 C66 C65 176.8(4) . . . . ?
C61 P2 C71 C76 -126.3(3) . . . . ?
C32 P2 C71 C76 132.5(3) . . . . ?
Ir1 P2 C71 C76 -1.9(3) . . . . ?
C61 P2 C71 C72 60.0(3) . . . . ?
C32 P2 C71 C72 -41.3(3) . . . . ?
Ir1 P2 C71 C72 -175.6(3) . . . . ?
C76 C71 C72 C73 -2.7(6) . . . . ?
P2 C71 C72 C73 171.2(3) . . . . ?
C71 C72 C73 C74 1.8(7) . . . . ?
C72 C73 C74 C75 0.3(7) . . . . ?
C73 C74 C75 C76 -1.5(7) . . . . ?
C74 C75 C76 C71 0.6(6) . . . . ?
C72 C71 C76 C75 1.5(5) . . . . ?
P2 C71 C76 C75 -172.5(3) . . . . ?
C86 Ir1 C81 C82 110.6(3) . . . . ?
C85 Ir1 C81 C82 71.9(3) . . . . ?
C21 Ir1 C81 C82 137.9(4) . . . . ?
P2 Ir1 C81 C82 -39.1(3) . . . . ?
P1 Ir1 C81 C82 -146.0(2) . . . . ?
C86 Ir1 C81 C88 -7.1(3) . . . . ?
C85 Ir1 C81 C88 -45.7(3) . . . . ?
C21 Ir1 C81 C88 20.3(6) . . . . ?
C82 Ir1 C81 C88 -117.6(4) . . . . ?
P2 Ir1 C81 C88 -156.7(3) . . . . ?
P1 Ir1 C81 C88 96.3(3) . . . . ?
C88 C81 C82 C83 1.9(6) . . . . ?
Ir1 C81 C82 C83 -105.7(4) . . . . ?
C88 C81 C82 Ir1 107.6(4) . . . . ?
C86 Ir1 C82 C81 -66.5(3) . . . . ?
C85 Ir1 C82 C81 -104.0(3) . . . . ?
C21 Ir1 C82 C81 -144.4(3) . . . . ?
P2 Ir1 C82 C81 142.7(2) . . . . ?
P1 Ir1 C82 C81 39.2(3) . . . . ?
C86 Ir1 C82 C83 52.2(3) . . . . ?
C85 Ir1 C82 C83 14.7(3) . . . . ?
C21 Ir1 C82 C83 -25.7(5) . . . . ?
C81 Ir1 C82 C83 118.7(4) . . . . ?
P2 Ir1 C82 C83 -98.5(3) . . . . ?
P1 Ir1 C82 C83 158.0(3) . . . . ?
C81 C82 C83 C84 62.0(6) . . . . ?
Ir1 C82 C83 C84 -20.1(5) . . . . ?
C82 C83 C84 C85 14.5(7) . . . . ?
C83 C84 C85 C86 -83.2(6) . . . . ?
C83 C84 C85 Ir1 -1.6(7) . . . . ?
C21 Ir1 C85 C86 -87.6(3) . . . . ?
C81 Ir1 C85 C86 73.2(3) . . . . ?
C82 Ir1 C85 C86 108.0(3) . . . . ?
P2 Ir1 C85 C86 -177.2(2) . . . . ?
P1 Ir1 C85 C86 -13.0(4) . . . . ?
C86 Ir1 C85 C84 -115.1(5) . . . . ?
C21 Ir1 C85 C84 157.2(4) . . . . ?
C81 Ir1 C85 C84 -42.0(4) . . . . ?
C82 Ir1 C85 C84 -7.1(4) . . . . ?
P2 Ir1 C85 C84 67.7(4) . . . . ?
P1 Ir1 C85 C84 -128.1(4) . . . . ?
C84 C85 C86 C87 -0.5(6) . . . . ?
Ir1 C85 C86 C87 -110.7(4) . . . . ?
C84 C85 C86 Ir1 110.2(4) . . . . ?
C21 Ir1 C86 C85 87.2(3) . . . . ?
C81 Ir1 C86 C85 -102.3(3) . . . . ?
C82 Ir1 C86 C85 -68.8(3) . . . . ?
P2 Ir1 C86 C85 5.3(4) . . . . ?
P1 Ir1 C86 C85 171.8(2) . . . . ?
C85 Ir1 C86 C87 117.6(5) . . . . ?
C21 Ir1 C86 C87 -155.2(4) . . . . ?
C81 Ir1 C86 C87 15.3(4) . . . . ?
C82 Ir1 C86 C87 48.8(4) . . . . ?
P2 Ir1 C86 C87 122.9(3) . . . . ?
P1 Ir1 C86 C87 -70.6(4) . . . . ?
C85 C86 C87 C88 62.7(6) . . . . ?
Ir1 C86 C87 C88 -20.7(6) . . . . ?
C82 C81 C88 C87 -85.2(5) . . . . ?
Ir1 C81 C88 C87 -1.8(5) . . . . ?
C86 C87 C88 C81 13.8(6) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1402758'
_audit_update_record             
;
2015-05-25 deposited with the CCDC.
2015-06-24 downloaded from the CCDC.
;

_audit_creation_date             2014-04-07T18:13:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C33 H34 Ir N2 O P2, F6 P, 3(C H2 Cl2)'
_chemical_formula_sum            'C36 H40 Cl6 F6 Ir N2 O P3'
_chemical_formula_weight         1128.51

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.5979(6)
_cell_length_b                   18.5435(10)
_cell_length_c                   20.1876(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.0000(10)
_cell_angle_gamma                90
_cell_volume                     4212.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9880
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.12

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plates
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2224
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_T_max  0.689

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0822
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_number            50129
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.941
_reflns_number_total             10123
_reflns_number_gt                6985
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0653P)²+31.4602P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         10123
_refine_ls_number_parameters     504
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1067
_refine_ls_R_factor_gt           0.0653
_refine_ls_wR_factor_ref         0.1575
_refine_ls_wR_factor_gt          0.1421
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.954
_refine_diff_density_min         -1.749
_refine_diff_density_rms         0.182

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.47909(3) 0.486008(18) 0.316206(15) 0.02459(11) Uani 1 1 d . . .
H1 H 0.456(9) 0.557(6) 0.365(5) 0.06(3) Uiso 1 1 d . . .
H2 H 0.457(8) 0.541(5) 0.257(5) 0.04(3) Uiso 1 1 d . . .
P1 P 0.27436(17) 0.48554(13) 0.28131(10) 0.0253(4) Uani 1 1 d . . .
P2 P 0.67650(17) 0.51306(13) 0.32549(10) 0.0247(4) Uani 1 1 d . . .
N1 N 0.3733(6) 0.4601(4) 0.1326(3) 0.0345(17) Uani 1 1 d . . .
C2 C 0.4727(8) 0.4362(5) 0.1773(4) 0.0304(19) Uani 1 1 d . . .
N3 N 0.5662(6) 0.4621(4) 0.1561(4) 0.0334(17) Uani 1 1 d . . .
C4 C 0.5254(9) 0.5049(6) 0.0986(4) 0.043(2) Uani 1 1 d . . .
H4 H 0.573 0.5304 0.0742 0.052 Uiso 1 1 calc R . .
C5 C 0.4061(8) 0.5034(5) 0.0839(4) 0.040(2) Uani 1 1 d . . .
H5 H 0.3538 0.5275 0.0471 0.048 Uiso 1 1 calc R . .
C11 C 0.2532(7) 0.4529(6) 0.1410(4) 0.037(2) Uani 1 1 d . . .
H111 H 0.2431 0.4034 0.157 0.044 Uiso 1 1 calc R . .
H112 H 0.1973 0.4587 0.0957 0.044 Uiso 1 1 calc R . .
C12 C 0.2189(7) 0.5065(5) 0.1907(4) 0.0294(19) Uani 1 1 d . . .
H121 H 0.1311 0.5094 0.1805 0.035 Uiso 1 1 calc R . .
H122 H 0.2486 0.5548 0.1821 0.035 Uiso 1 1 calc R . .
C21 C 0.4791(8) 0.3982(5) 0.2405(4) 0.035(2) Uani 1 1 d . . .
H211 H 0.5527 0.3691 0.2536 0.042 Uiso 1 1 calc R . .
H212 H 0.4096 0.366 0.2367 0.042 Uiso 1 1 calc R . .
C31 C 0.6893(8) 0.4581(5) 0.1957(4) 0.034(2) Uani 1 1 d . . .
H311 H 0.7429 0.4573 0.1643 0.041 Uiso 1 1 calc R . .
H312 H 0.7013 0.4128 0.2225 0.041 Uiso 1 1 calc R . .
C32 C 0.7207(8) 0.5228(5) 0.2443(4) 0.0302(19) Uani 1 1 d . . .
H321 H 0.682 0.5664 0.2206 0.036 Uiso 1 1 calc R . .
H322 H 0.8077 0.5305 0.2545 0.036 Uiso 1 1 calc R . .
C41 C 0.2016(7) 0.5502(4) 0.3257(4) 0.0239(16) Uani 1 1 d . . .
C42 C 0.2358(8) 0.5502(5) 0.3969(4) 0.035(2) Uani 1 1 d . . .
H42 H 0.2968 0.5184 0.4198 0.042 Uiso 1 1 calc R . .
C43 C 0.1820(8) 0.5958(5) 0.4343(5) 0.037(2) Uani 1 1 d . . .
H43 H 0.205 0.5948 0.4827 0.045 Uiso 1 1 calc R . .
C44 C 0.0944(8) 0.6432(5) 0.4011(5) 0.038(2) Uani 1 1 d . . .
H44 H 0.0569 0.6745 0.4267 0.045 Uiso 1 1 calc R . .
C45 C 0.0620(8) 0.6446(5) 0.3312(4) 0.035(2) Uani 1 1 d . . .
H45 H 0.003 0.6777 0.3085 0.042 Uiso 1 1 calc R . .
C46 C 0.1143(7) 0.5981(5) 0.2929(4) 0.0278(18) Uani 1 1 d . . .
H46 H 0.0904 0.5991 0.2444 0.033 Uiso 1 1 calc R . .
C51 C 0.1955(7) 0.4023(5) 0.2894(4) 0.0298(19) Uani 1 1 d . . .
C52 C 0.2544(8) 0.3410(5) 0.3191(4) 0.034(2) Uani 1 1 d . . .
H52 H 0.3385 0.3414 0.335 0.041 Uiso 1 1 calc R . .
C53 C 0.1910(10) 0.2785(5) 0.3260(5) 0.046(3) Uani 1 1 d . . .
H53 H 0.2318 0.2368 0.3467 0.056 Uiso 1 1 calc R . .
C54 C 0.0677(10) 0.2775(5) 0.3023(5) 0.044(3) Uani 1 1 d . . .
H54 H 0.0244 0.2349 0.3064 0.053 Uiso 1 1 calc R . .
C55 C 0.0085(9) 0.3387(6) 0.2726(5) 0.042(2) Uani 1 1 d . . .
H55 H -0.0755 0.3378 0.2566 0.051 Uiso 1 1 calc R . .
C56 C 0.0701(8) 0.4008(5) 0.2661(5) 0.036(2) Uani 1 1 d . . .
H56 H 0.0284 0.4426 0.2461 0.044 Uiso 1 1 calc R . .
C61 C 0.7188(7) 0.5991(5) 0.3681(4) 0.0291(19) Uani 1 1 d . . .
C62 C 0.7060(8) 0.6086(5) 0.4340(5) 0.040(2) Uani 1 1 d . . .
H62 H 0.6782 0.5698 0.4566 0.048 Uiso 1 1 calc R . .
C63 C 0.7329(9) 0.6737(6) 0.4673(5) 0.050(3) Uani 1 1 d . . .
H63 H 0.7251 0.6789 0.5129 0.06 Uiso 1 1 calc R . .
C64 C 0.7709(9) 0.7309(6) 0.4351(7) 0.056(3) Uani 1 1 d . . .
H64 H 0.7899 0.7755 0.4583 0.068 Uiso 1 1 calc R . .
C65 C 0.7817(9) 0.7237(6) 0.3685(7) 0.055(3) Uani 1 1 d . . .
H65 H 0.806 0.7635 0.3455 0.065 Uiso 1 1 calc R . .
C66 C 0.7569(8) 0.6584(5) 0.3360(5) 0.040(2) Uani 1 1 d . . .
H66 H 0.7658 0.6533 0.2907 0.048 Uiso 1 1 calc R . .
C71 C 0.7876(7) 0.4497(5) 0.3710(4) 0.0256(17) Uani 1 1 d . . .
C72 C 0.9040(8) 0.4720(5) 0.4001(4) 0.033(2) Uani 1 1 d . . .
H72 H 0.9251 0.5214 0.3987 0.039 Uiso 1 1 calc R . .
C73 C 0.9882(7) 0.4221(5) 0.4309(4) 0.035(2) Uani 1 1 d . . .
H73 H 1.0667 0.4378 0.4515 0.042 Uiso 1 1 calc R . .
C74 C 0.9611(8) 0.3505(6) 0.4324(5) 0.039(2) Uani 1 1 d . . .
H74 H 1.0203 0.3168 0.4535 0.047 Uiso 1 1 calc R . .
C75 C 0.8456(8) 0.3273(5) 0.4025(5) 0.038(2) Uani 1 1 d . . .
H75 H 0.8262 0.2775 0.4023 0.045 Uiso 1 1 calc R . .
C76 C 0.7601(7) 0.3770(5) 0.3734(4) 0.0302(19) Uani 1 1 d . . .
H76 H 0.681 0.3613 0.3546 0.036 Uiso 1 1 calc R . .
C81 C 0.4998(8) 0.4311(6) 0.3989(5) 0.041(2) Uani 1 1 d . . .
O82 O 0.5132(6) 0.4052(5) 0.4521(4) 0.059(2) Uani 1 1 d . . .
P10 P 0.1231(2) 0.07408(15) 0.41456(12) 0.0375(6) Uani 1 1 d . . .
F11 F 0.2119(5) 0.0068(3) 0.4405(3) 0.0497(15) Uani 1 1 d . . .
F12 F 0.0325(7) 0.1374(4) 0.3885(3) 0.071(2) Uani 1 1 d . . .
F13 F 0.0840(5) 0.0361(4) 0.3414(3) 0.0585(18) Uani 1 1 d . . .
F14 F 0.0178(5) 0.0315(3) 0.4365(3) 0.0534(16) Uani 1 1 d . . .
F15 F 0.1619(7) 0.1076(4) 0.4889(3) 0.073(2) Uani 1 1 d . . .
F16 F 0.2289(6) 0.1126(4) 0.3915(4) 0.0667(19) Uani 1 1 d . . .
Cl91 Cl 0.6863(4) 0.2400(3) 0.2171(6) 0.244(5) Uani 1 1 d U . .
C92 C 0.5478(16) 0.2100(9) 0.2077(10) 0.125(8) Uani 1 1 d U . .
H921 H 0.5379 0.1619 0.1858 0.15 Uiso 1 1 calc R . .
H922 H 0.4899 0.2437 0.1795 0.15 Uiso 1 1 calc R . .
Cl93 Cl 0.5275(8) 0.2052(3) 0.2957(3) 0.184(3) Uani 1 1 d U . .
Cl94 Cl 0.9394(5) 0.3420(3) 0.1072(2) 0.1083(15) Uani 1 1 d U . .
C95 C 0.9070(17) 0.3561(10) 0.0227(8) 0.111(7) Uani 1 1 d U . .
H951 H 0.9265 0.4069 0.0147 0.133 Uiso 1 1 calc R . .
H952 H 0.9596 0.3251 0.0029 0.133 Uiso 1 1 calc R . .
Cl96 Cl 0.7688(7) 0.3410(4) -0.0192(5) 0.247(6) Uani 1 1 d U . .
Cl97 Cl 0.5140(14) 0.3156(9) 0.0554(12) 0.475(13) Uani 1 1 d U . .
C98 C 0.564(4) 0.263(2) 0.0096(17) 0.35(3) Uani 1 1 d U . .
H981 H 0.5523 0.2143 0.0256 0.415 Uiso 1 1 calc R . .
H982 H 0.6514 0.2715 0.0212 0.415 Uiso 1 1 calc R . .
Cl99 Cl 0.5208(11) 0.2603(7) -0.0789(9) 0.351(9) Uani 1 1 d U . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C81 1.921(10) . ?
Ir1 C21 2.234(9) . ?
Ir1 P2 2.307(2) . ?
Ir1 P1 2.308(2) . ?
Ir1 H1 1.70(10) . ?
Ir1 H2 1.54(9) . ?
P1 C51 1.820(9) . ?
P1 C41 1.822(8) . ?
P1 C12 1.828(8) . ?
P2 C71 1.820(8) . ?
P2 C61 1.823(9) . ?
P2 C32 1.840(8) . ?
N1 C2 1.354(10) . ?
N1 C5 1.392(12) . ?
N1 C11 1.449(11) . ?
C2 N3 1.347(11) . ?
C2 C21 1.445(12) . ?
N3 C4 1.391(12) . ?
N3 C31 1.459(10) . ?
C4 C5 1.343(14) . ?
C4 H4 0.95 . ?
C5 H5 0.95 . ?
C11 C12 1.534(12) . ?
C11 H111 0.99 . ?
C11 H112 0.99 . ?
C12 H121 0.99 . ?
C12 H122 0.99 . ?
C21 H211 0.99 . ?
C21 H212 0.99 . ?
C31 C32 1.537(12) . ?
C31 H311 0.99 . ?
C31 H312 0.99 . ?
C32 H321 0.99 . ?
C32 H322 0.99 . ?
C41 C46 1.389(11) . ?
C41 C42 1.395(11) . ?
C42 C43 1.379(13) . ?
C42 H42 0.95 . ?
C43 C44 1.388(12) . ?
C43 H43 0.95 . ?
C44 C45 1.370(12) . ?
C44 H44 0.95 . ?
C45 C46 1.392(12) . ?
C45 H45 0.95 . ?
C46 H46 0.95 . ?
C51 C52 1.387(12) . ?
C51 C56 1.417(12) . ?
C52 C53 1.397(13) . ?
C52 H52 0.95 . ?
C53 C54 1.394(15) . ?
C53 H53 0.95 . ?
C54 C55 1.385(14) . ?
C54 H54 0.95 . ?
C55 C56 1.379(13) . ?
C55 H55 0.95 . ?
C56 H56 0.95 . ?
C61 C62 1.386(13) . ?
C61 C66 1.400(13) . ?
C62 C63 1.380(13) . ?
C62 H62 0.95 . ?
C63 C64 1.373(17) . ?
C63 H63 0.95 . ?
C64 C65 1.386(17) . ?
C64 H64 0.95 . ?
C65 C66 1.373(14) . ?
C65 H65 0.95 . ?
C66 H66 0.95 . ?
C71 C76 1.389(12) . ?
C71 C72 1.398(11) . ?
C72 C73 1.380(12) . ?
C72 H72 0.95 . ?
C73 C74 1.367(14) . ?
C73 H73 0.95 . ?
C74 C75 1.397(13) . ?
C74 H74 0.95 . ?
C75 C76 1.378(12) . ?
C75 H75 0.95 . ?
C76 H76 0.95 . ?
C81 O82 1.150(11) . ?
P10 F12 1.578(7) . ?
P10 F16 1.584(6) . ?
P10 F15 1.586(6) . ?
P10 F13 1.601(6) . ?
P10 F14 1.603(6) . ?
P10 F11 1.621(6) . ?
Cl91 C92 1.667(19) . ?
C92 Cl93 1.85(2) . ?
C92 H921 0.99 . ?
C92 H922 0.99 . ?
Cl94 C95 1.675(15) . ?
C95 Cl96 1.646(19) . ?
C95 H951 0.99 . ?
C95 H952 0.99 . ?
Cl97 C98 1.55(3) . ?
C98 Cl99 1.74(3) . ?
C98 H981 0.99 . ?
C98 H982 0.99 . ?

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
C81 Ir1 C21 100.8(4) . . ?
C81 Ir1 P2 97.6(3) . . ?
C21 Ir1 P2 92.9(2) . . ?
C81 Ir1 P1 99.6(3) . . ?
C21 Ir1 P1 87.6(2) . . ?
P2 Ir1 P1 162.44(8) . . ?
C81 Ir1 H1 84(3) . . ?
C21 Ir1 H1 170(3) . . ?
P2 Ir1 H1 95(3) . . ?
P1 Ir1 H1 83(3) . . ?
C81 Ir1 H2 170(3) . . ?
C21 Ir1 H2 89(3) . . ?
P2 Ir1 H2 84(3) . . ?
P1 Ir1 H2 79(3) . . ?
H1 Ir1 H2 86(5) . . ?
C51 P1 C41 102.2(4) . . ?
C51 P1 C12 101.9(4) . . ?
C41 P1 C12 105.0(4) . . ?
C51 P1 Ir1 118.5(3) . . ?
C41 P1 Ir1 114.3(3) . . ?
C12 P1 Ir1 113.1(3) . . ?
C71 P2 C61 104.5(4) . . ?
C71 P2 C32 101.3(4) . . ?
C61 P2 C32 103.5(4) . . ?
C71 P2 Ir1 117.9(3) . . ?
C61 P2 Ir1 112.2(3) . . ?
C32 P2 Ir1 115.7(3) . . ?
C2 N1 C5 109.0(7) . . ?
C2 N1 C11 125.4(8) . . ?
C5 N1 C11 124.7(8) . . ?
N3 C2 N1 107.0(8) . . ?
N3 C2 C21 125.5(8) . . ?
N1 C2 C21 127.0(8) . . ?
C2 N3 C4 109.3(7) . . ?
C2 N3 C31 124.3(7) . . ?
C4 N3 C31 125.2(8) . . ?
C5 C4 N3 107.3(9) . . ?
C5 C4 H4 126.4 . . ?
N3 C4 H4 126.4 . . ?
C4 C5 N1 107.4(8) . . ?
C4 C5 H5 126.3 . . ?
N1 C5 H5 126.3 . . ?
N1 C11 C12 115.2(7) . . ?
N1 C11 H111 108.5 . . ?
C12 C11 H111 108.5 . . ?
N1 C11 H112 108.5 . . ?
C12 C11 H112 108.5 . . ?
H111 C11 H112 107.5 . . ?
C11 C12 P1 115.6(6) . . ?
C11 C12 H121 108.4 . . ?
P1 C12 H121 108.4 . . ?
C11 C12 H122 108.4 . . ?
P1 C12 H122 108.4 . . ?
H121 C12 H122 107.4 . . ?
C2 C21 Ir1 103.9(6) . . ?
C2 C21 H211 111 . . ?
Ir1 C21 H211 111 . . ?
C2 C21 H212 111 . . ?
Ir1 C21 H212 111 . . ?
H211 C21 H212 109 . . ?
N3 C31 C32 111.1(7) . . ?
N3 C31 H311 109.4 . . ?
C32 C31 H311 109.4 . . ?
N3 C31 H312 109.4 . . ?
C32 C31 H312 109.4 . . ?
H311 C31 H312 108 . . ?
C31 C32 P2 114.7(6) . . ?
C31 C32 H321 108.6 . . ?
P2 C32 H321 108.6 . . ?
C31 C32 H322 108.6 . . ?
P2 C32 H322 108.6 . . ?
H321 C32 H322 107.6 . . ?
C46 C41 C42 119.0(8) . . ?
C46 C41 P1 123.8(6) . . ?
C42 C41 P1 117.2(6) . . ?
C43 C42 C41 120.6(8) . . ?
C43 C42 H42 119.7 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 120.0(8) . . ?
C42 C43 H43 120 . . ?
C44 C43 H43 120 . . ?
C45 C44 C43 119.7(9) . . ?
C45 C44 H44 120.1 . . ?
C43 C44 H44 120.1 . . ?
C44 C45 C46 120.9(8) . . ?
C44 C45 H45 119.6 . . ?
C46 C45 H45 119.6 . . ?
C41 C46 C45 119.8(8) . . ?
C41 C46 H46 120.1 . . ?
C45 C46 H46 120.1 . . ?
C52 C51 C56 119.1(8) . . ?
C52 C51 P1 121.9(7) . . ?
C56 C51 P1 119.0(7) . . ?
C51 C52 C53 120.5(9) . . ?
C51 C52 H52 119.8 . . ?
C53 C52 H52 119.8 . . ?
C54 C53 C52 119.9(9) . . ?
C54 C53 H53 120.1 . . ?
C52 C53 H53 120.1 . . ?
C55 C54 C53 119.8(9) . . ?
C55 C54 H54 120.1 . . ?
C53 C54 H54 120.1 . . ?
C56 C55 C54 120.8(9) . . ?
C56 C55 H55 119.6 . . ?
C54 C55 H55 119.6 . . ?
C55 C56 C51 119.9(9) . . ?
C55 C56 H56 120 . . ?
C51 C56 H56 120 . . ?
C62 C61 C66 117.6(9) . . ?
C62 C61 P2 119.0(7) . . ?
C66 C61 P2 123.2(7) . . ?
C63 C62 C61 121.0(10) . . ?
C63 C62 H62 119.5 . . ?
C61 C62 H62 119.5 . . ?
C64 C63 C62 120.4(10) . . ?
C64 C63 H63 119.8 . . ?
C62 C63 H63 119.8 . . ?
C63 C64 C65 120.0(10) . . ?
C63 C64 H64 120 . . ?
C65 C64 H64 120 . . ?
C66 C65 C64 119.4(11) . . ?
C66 C65 H65 120.3 . . ?
C64 C65 H65 120.3 . . ?
C65 C66 C61 121.6(10) . . ?
C65 C66 H66 119.2 . . ?
C61 C66 H66 119.2 . . ?
C76 C71 C72 118.6(8) . . ?
C76 C71 P2 120.2(6) . . ?
C72 C71 P2 121.0(7) . . ?
C73 C72 C71 119.8(8) . . ?
C73 C72 H72 120.1 . . ?
C71 C72 H72 120.1 . . ?
C74 C73 C72 121.3(8) . . ?
C74 C73 H73 119.3 . . ?
C72 C73 H73 119.3 . . ?
C73 C74 C75 119.4(8) . . ?
C73 C74 H74 120.3 . . ?
C75 C74 H74 120.3 . . ?
C76 C75 C74 119.6(9) . . ?
C76 C75 H75 120.2 . . ?
C74 C75 H75 120.2 . . ?
C75 C76 C71 121.1(8) . . ?
C75 C76 H76 119.4 . . ?
C71 C76 H76 119.4 . . ?
O82 C81 Ir1 172.6(10) . . ?
F12 P10 F16 93.9(4) . . ?
F12 P10 F15 92.1(4) . . ?
F16 P10 F15 92.2(4) . . ?
F12 P10 F13 90.2(4) . . ?
F16 P10 F13 89.6(4) . . ?
F15 P10 F13 176.9(4) . . ?
F12 P10 F14 88.2(4) . . ?
F16 P10 F14 177.2(4) . . ?
F15 P10 F14 89.6(4) . . ?
F13 P10 F14 88.5(3) . . ?
F12 P10 F11 177.8(4) . . ?
F16 P10 F11 87.9(4) . . ?
F15 P10 F11 89.1(4) . . ?
F13 P10 F11 88.6(3) . . ?
F14 P10 F11 90.0(3) . . ?
Cl91 C92 Cl93 104.5(10) . . ?
Cl91 C92 H921 110.9 . . ?
Cl93 C92 H921 110.9 . . ?
Cl91 C92 H922 110.9 . . ?
Cl93 C92 H922 110.9 . . ?
H921 C92 H922 108.9 . . ?
Cl96 C95 Cl94 116.6(13) . . ?
Cl96 C95 H951 108.1 . . ?
Cl94 C95 H951 108.1 . . ?
Cl96 C95 H952 108.1 . . ?
Cl94 C95 H952 108.1 . . ?
H951 C95 H952 107.3 . . ?
Cl97 C98 Cl99 125(3) . . ?
Cl97 C98 H981 106 . . ?
Cl99 C98 H981 106 . . ?
Cl97 C98 H982 106 . . ?
Cl99 C98 H982 106 . . ?
H981 C98 H982 106.3 . . ?

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
C81 Ir1 P1 C51 -41.7(4) . . . . ?
C21 Ir1 P1 C51 58.8(4) . . . . ?
P2 Ir1 P1 C51 150.8(4) . . . . ?
C81 Ir1 P1 C41 78.9(4) . . . . ?
C21 Ir1 P1 C41 179.5(4) . . . . ?
P2 Ir1 P1 C41 -88.5(4) . . . . ?
C81 Ir1 P1 C12 -160.9(4) . . . . ?
C21 Ir1 P1 C12 -60.3(4) . . . . ?
P2 Ir1 P1 C12 31.7(4) . . . . ?
C81 Ir1 P2 C71 28.9(4) . . . . ?
C21 Ir1 P2 C71 -72.4(4) . . . . ?
P1 Ir1 P2 C71 -163.6(3) . . . . ?
C81 Ir1 P2 C61 -92.6(4) . . . . ?
C21 Ir1 P2 C61 166.1(4) . . . . ?
P1 Ir1 P2 C61 74.9(4) . . . . ?
C81 Ir1 P2 C32 149.0(5) . . . . ?
C21 Ir1 P2 C32 47.7(4) . . . . ?
P1 Ir1 P2 C32 -43.5(5) . . . . ?
C5 N1 C2 N3 -1.8(10) . . . . ?
C11 N1 C2 N3 -171.5(8) . . . . ?
C5 N1 C2 C21 171.0(9) . . . . ?
C11 N1 C2 C21 1.3(14) . . . . ?
N1 C2 N3 C4 2.1(10) . . . . ?
C21 C2 N3 C4 -170.8(8) . . . . ?
N1 C2 N3 C31 170.1(8) . . . . ?
C21 C2 N3 C31 -2.8(14) . . . . ?
C2 N3 C4 C5 -1.6(10) . . . . ?
C31 N3 C4 C5 -169.5(8) . . . . ?
N3 C4 C5 N1 0.4(11) . . . . ?
C2 N1 C5 C4 0.8(10) . . . . ?
C11 N1 C5 C4 170.6(8) . . . . ?
C2 N1 C11 C12 77.8(11) . . . . ?
C5 N1 C11 C12 -90.4(10) . . . . ?
N1 C11 C12 P1 -78.4(9) . . . . ?
C51 P1 C12 C11 -65.5(7) . . . . ?
C41 P1 C12 C11 -171.8(6) . . . . ?
Ir1 P1 C12 C11 62.8(7) . . . . ?
N3 C2 C21 Ir1 86.5(9) . . . . ?
N1 C2 C21 Ir1 -85.0(9) . . . . ?
C81 Ir1 C21 C2 -175.9(6) . . . . ?
P2 Ir1 C21 C2 -77.6(6) . . . . ?
P1 Ir1 C21 C2 84.8(6) . . . . ?
C2 N3 C31 C32 -86.8(10) . . . . ?
C4 N3 C31 C32 79.4(10) . . . . ?
N3 C31 C32 P2 83.0(8) . . . . ?
C71 P2 C32 C31 74.8(7) . . . . ?
C61 P2 C32 C31 -177.1(6) . . . . ?
Ir1 P2 C32 C31 -54.0(7) . . . . ?
C51 P1 C41 C46 -100.1(7) . . . . ?
C12 P1 C41 C46 6.0(8) . . . . ?
Ir1 P1 C41 C46 130.5(6) . . . . ?
C51 P1 C41 C42 79.1(7) . . . . ?
C12 P1 C41 C42 -174.8(7) . . . . ?
Ir1 P1 C41 C42 -50.3(7) . . . . ?
C46 C41 C42 C43 1.5(13) . . . . ?
P1 C41 C42 C43 -177.8(7) . . . . ?
C41 C42 C43 C44 -1.1(15) . . . . ?
C42 C43 C44 C45 -0.3(15) . . . . ?
C43 C44 C45 C46 1.2(15) . . . . ?
C42 C41 C46 C45 -0.5(12) . . . . ?
P1 C41 C46 C45 178.7(7) . . . . ?
C44 C45 C46 C41 -0.8(14) . . . . ?
C41 P1 C51 C52 -123.1(8) . . . . ?
C12 P1 C51 C52 128.4(8) . . . . ?
Ir1 P1 C51 C52 3.6(9) . . . . ?
C41 P1 C51 C56 55.2(8) . . . . ?
C12 P1 C51 C56 -53.2(8) . . . . ?
Ir1 P1 C51 C56 -178.1(6) . . . . ?
C56 C51 C52 C53 0.1(14) . . . . ?
P1 C51 C52 C53 178.5(7) . . . . ?
C51 C52 C53 C54 0.5(14) . . . . ?
C52 C53 C54 C55 -0.6(15) . . . . ?
C53 C54 C55 C56 0.1(15) . . . . ?
C54 C55 C56 C51 0.6(15) . . . . ?
C52 C51 C56 C55 -0.7(13) . . . . ?
P1 C51 C56 C55 -179.1(7) . . . . ?
C71 P2 C61 C62 -69.5(7) . . . . ?
C32 P2 C61 C62 -175.2(7) . . . . ?
Ir1 P2 C61 C62 59.4(7) . . . . ?
C71 P2 C61 C66 114.7(7) . . . . ?
C32 P2 C61 C66 9.0(8) . . . . ?
Ir1 P2 C61 C66 -116.4(7) . . . . ?
C66 C61 C62 C63 -1.7(13) . . . . ?
P2 C61 C62 C63 -177.7(7) . . . . ?
C61 C62 C63 C64 1.3(15) . . . . ?
C62 C63 C64 C65 0.4(15) . . . . ?
C63 C64 C65 C66 -1.6(15) . . . . ?
C64 C65 C66 C61 1.2(15) . . . . ?
C62 C61 C66 C65 0.5(13) . . . . ?
P2 C61 C66 C65 176.3(7) . . . . ?
C61 P2 C71 C76 153.0(7) . . . . ?
C32 P2 C71 C76 -99.7(7) . . . . ?
Ir1 P2 C71 C76 27.7(7) . . . . ?
C61 P2 C71 C72 -31.4(8) . . . . ?
C32 P2 C71 C72 75.9(7) . . . . ?
Ir1 P2 C71 C72 -156.7(6) . . . . ?
C76 C71 C72 C73 -0.6(12) . . . . ?
P2 C71 C72 C73 -176.3(6) . . . . ?
C71 C72 C73 C74 1.5(13) . . . . ?
C72 C73 C74 C75 -0.5(14) . . . . ?
C73 C74 C75 C76 -1.4(14) . . . . ?
C74 C75 C76 C71 2.3(13) . . . . ?
C72 C71 C76 C75 -1.2(12) . . . . ?
P2 C71 C76 C75 174.5(7) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
