# Electronic Supplementary Material (ESI) for RSC Advances.
# 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 1055780'
_audit_update_record             
;
2015-03-24 deposited with the CCDC.
2015-05-01 downloaded from the CCDC.
;

#see the bottom part of the file for the full list of the applied restraints. 

#end of refcif 
_cell_length_a                   25.335(3)
_cell_length_b                   12.8383(13)
_cell_length_c                   24.821(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.755(4)
_cell_angle_gamma                90
_cell_volume                     7598.2(8)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
P 0.2955 0.4335 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645
1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Ir -4.7710 6.5667 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011
11.4722 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C36 H34 F6 Ir1 N6 O4 P1 S2 
# Dc =      1.78 Fooo =   3967.99 Mu =     89.20 M =   1016.02
# Found Formula = C36 H28 F6 Ir1 N6 O4 P1 S2 
# Dc =      1.77 FOOO =   3967.99 Mu =     89.20 M =   1009.97

_chemical_formula_sum            'C36 H28 F6 Ir1 N6 O4 P1 S2'
_chemical_formula_moiety         'C34 H25 Ir N5 O4 S2, F6 P, C2 H3 N'
_chemical_compound_source        ?
_chemical_formula_weight         1009.97


_cell_measurement_reflns_used    9253
_cell_measurement_theta_min      4
_cell_measurement_theta_max      69
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_max          0.190

_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             3967.986
_exptl_absorpt_coefficient_mu    8.920

# Sheldrick geometric approximatio 0.37 0.77 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_T_max  0.77
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            50748
_reflns_number_total             6985
_diffrn_reflns_av_R_equivalents  0.049
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6985 
# Theoretical number of reflections is about 14165 


_diffrn_reflns_theta_min         3.707
_diffrn_reflns_theta_max         69.113
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       27
_reflns_limit_h_min              -30
_reflns_limit_h_max              28
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.57
_refine_diff_density_max         0.98


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         6361
_refine_ls_number_restraints     0
_refine_ls_number_parameters     505
_oxford_refine_ls_R_factor_ref   0.0226
_refine_ls_wR_factor_ref         0.0248
_refine_ls_goodness_of_fit_ref   1.0886
_refine_ls_shift/su_max          0.0035958
_refine_ls_shift/su_mean         0.0000854


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6954
_refine_ls_R_factor_all          0.0251
_refine_ls_wR_factor_all         0.0282

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6664
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_gt          0.0257

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.157 0.108 0.539E-01 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Ir1 Ir 0.308518(4) 0.614848(8) 0.697734(4) 0.0118 1.0000 Uani . . . . . .
N1 N 0.26765(9) 0.47772(17) 0.65382(9) 0.0147 1.0000 Uani . . . . . .
N2 N 0.31669(9) 0.51456(17) 0.59280(9) 0.0165 1.0000 Uani . . . . . .
N3 N 0.34086(9) 0.59558(17) 0.62971(9) 0.0166 1.0000 Uani . . . . . .
N4 N 0.37961(9) 0.54781(16) 0.75320(9) 0.0157 1.0000 Uani . . . . . .
N5 N 0.23954(8) 0.69696(16) 0.64965(9) 0.0139 1.0000 Uani . . . . . .
C1 C 0.22911(11) 0.4231(2) 0.66862(11) 0.0179 1.0000 Uani . . . . . .
C2 C 0.19408(11) 0.3512(2) 0.63275(12) 0.0207 1.0000 Uani . . . . . .
C3 C 0.19804(11) 0.3364(2) 0.57888(12) 0.0220 1.0000 Uani . . . . . .
C4 C 0.23798(11) 0.3899(2) 0.56333(11) 0.0207 1.0000 Uani . . . . . .
C5 C 0.27325(10) 0.4586(2) 0.60285(10) 0.0154 1.0000 Uani . . . . . .
C6 C 0.34385(11) 0.5016(2) 0.55387(11) 0.0195 1.0000 Uani . . . . . .
C7 C 0.38477(11) 0.5758(2) 0.56614(11) 0.0215 1.0000 Uani . . . . . .
C8 C 0.38148(11) 0.6335(2) 0.61300(11) 0.0195 1.0000 Uani . . . . . .
C9 C 0.32940(13) 0.4209(3) 0.50804(12) 0.0287 1.0000 Uani . . . . . .
C10 C 0.41567(12) 0.7243(2) 0.64209(14) 0.0283 1.0000 Uani . . . . . .
C11 C 0.39412(11) 0.4473(2) 0.75213(12) 0.0201 1.0000 Uani . . . . . .
C12 C 0.44082(12) 0.4054(2) 0.79302(13) 0.0265 1.0000 Uani . . . . . .
C13 C 0.47276(12) 0.4680(2) 0.83767(13) 0.0285 1.0000 Uani . . . . . .
C14 C 0.45904(12) 0.5721(2) 0.83779(13) 0.0259 1.0000 Uani . . . . . .
C15 C 0.41362(11) 0.6122(2) 0.79418(11) 0.0174 1.0000 Uani . . . . . .
C16 C 0.39743(10) 0.7221(2) 0.78469(11) 0.0158 1.0000 Uani . . . . . .
C17 C 0.43029(11) 0.8032(2) 0.81647(11) 0.0186 1.0000 Uani . . . . . .
C18 C 0.41385(11) 0.9049(2) 0.80066(11) 0.0189 1.0000 Uani . . . . . .
C19 C 0.36551(11) 0.9273(2) 0.75490(11) 0.0192 1.0000 Uani . . . . . .
C20 C 0.33310(10) 0.8465(2) 0.72378(11) 0.0176 1.0000 Uani . . . . . .
C21 C 0.34833(10) 0.7425(2) 0.73711(10) 0.0146 1.0000 Uani . . . . . .
C22 C 0.42922(14) 1.0296(3) 0.89648(14) 0.0334 1.0000 Uani . . . . . .
C23 C 0.23193(11) 0.7337(2) 0.59684(11) 0.0196 1.0000 Uani . . . . . .
C24 C 0.18618(12) 0.7932(2) 0.56696(12) 0.0257 1.0000 Uani . . . . . .
C25 C 0.14580(12) 0.8143(2) 0.59190(12) 0.0268 1.0000 Uani . . . . . .
C26 C 0.15337(11) 0.7763(2) 0.64620(11) 0.0221 1.0000 Uani . . . . . .
C27 C 0.20119(10) 0.7192(2) 0.67527(10) 0.0147 1.0000 Uani . . . . . .
C28 C 0.21622(10) 0.67860(19) 0.73393(10) 0.0144 1.0000 Uani . . . . . .
C29 C 0.18340(10) 0.69625(19) 0.76820(11) 0.0152 1.0000 Uani . . . . . .
C30 C 0.20104(11) 0.6561(2) 0.82365(11) 0.0175 1.0000 Uani . . . . . .
C31 C 0.24898(11) 0.5962(2) 0.84358(11) 0.0191 1.0000 Uani . . . . . .
C32 C 0.28188(11) 0.5802(2) 0.80932(11) 0.0173 1.0000 Uani . . . . . .
C33 C 0.26726(11) 0.62261(19) 0.75412(11) 0.0149 1.0000 Uani . . . . . .
C34 C 0.10319(14) 0.6008(3) 0.84738(14) 0.0332 1.0000 Uani . . . . . .
S1 S 0.45501(3) 1.00817(5) 0.83949(3) 0.0226 1.0000 Uani . . . . . .
S2 S 0.16119(3) 0.68597(5) 0.86814(3) 0.0180 1.0000 Uani . . . . . .
O1 O 0.51166(8) 0.97126(17) 0.86336(10) 0.0331 1.0000 Uani . . . . . .
O2 O 0.44346(10) 1.09958(16) 0.80367(10) 0.0322 1.0000 Uani . . . . . .
O3 O 0.19511(8) 0.66274(17) 0.92639(8) 0.0261 1.0000 Uani . . . . . .
O4 O 0.14022(8) 0.79023(16) 0.85465(8) 0.0247 1.0000 Uani . . . . . .
H11 H 0.2257 0.4339 0.7044 0.0218 1.0000 Uiso R . . . . .
H21 H 0.1689 0.3145 0.6447 0.0250 1.0000 Uiso R . . . . .
H31 H 0.1747 0.2900 0.5537 0.0269 1.0000 Uiso R . . . . .
H41 H 0.2406 0.3820 0.5279 0.0250 1.0000 Uiso R . . . . .
H71 H 0.4102 0.5866 0.5474 0.0259 1.0000 Uiso R . . . . .
H91 H 0.3567 0.4230 0.4892 0.0436 1.0000 Uiso R . . . . .
H92 H 0.3294 0.3544 0.5244 0.0438 1.0000 Uiso R . . . . .
H93 H 0.2930 0.4358 0.4807 0.0437 1.0000 Uiso R . . . . .
H101 H 0.4418 0.7034 0.6785 0.0428 1.0000 Uiso R . . . . .
H102 H 0.4352 0.7523 0.6190 0.0424 1.0000 Uiso R . . . . .
H103 H 0.3922 0.7774 0.6480 0.0427 1.0000 Uiso R . . . . .
H111 H 0.3712 0.4056 0.7235 0.0245 1.0000 Uiso R . . . . .
H121 H 0.4500 0.3370 0.7909 0.0321 1.0000 Uiso R . . . . .
H131 H 0.5031 0.4408 0.8665 0.0349 1.0000 Uiso R . . . . .
H141 H 0.4802 0.6162 0.8672 0.0304 1.0000 Uiso R . . . . .
H171 H 0.4625 0.7894 0.8467 0.0224 1.0000 Uiso R . . . . .
H191 H 0.3551 0.9950 0.7453 0.0229 1.0000 Uiso R . . . . .
H201 H 0.3004 0.8628 0.6934 0.0207 1.0000 Uiso R . . . . .
H231 H 0.2582 0.7189 0.5794 0.0240 1.0000 Uiso R . . . . .
H241 H 0.1833 0.8194 0.5311 0.0311 1.0000 Uiso R . . . . .
H251 H 0.1143 0.8530 0.5723 0.0330 1.0000 Uiso R . . . . .
H261 H 0.1268 0.7884 0.6631 0.0269 1.0000 Uiso R . . . . .
H291 H 0.1508 0.7351 0.7547 0.0183 1.0000 Uiso R . . . . .
H311 H 0.2592 0.5661 0.8794 0.0232 1.0000 Uiso R . . . . .
H321 H 0.3143 0.5405 0.8243 0.0208 1.0000 Uiso R . . . . .
P1 P 0.47138(3) 0.72793(6) 0.99989(3) 0.0303 1.0000 Uani . . . . . .
F1 F 0.42308(9) 0.7210(2) 0.93929(9) 0.0582 1.0000 Uani . . . . . .
F2 F 0.46016(12) 0.61130(19) 1.01170(14) 0.0746 1.0000 Uani . . . . . .
F3 F 0.51899(9) 0.73469(18) 1.06146(9) 0.0499 1.0000 Uani . . . . . .
F4 F 0.48190(12) 0.8482(2) 0.99055(12) 0.0735 1.0000 Uani . . . . . .
F5 F 0.42577(10) 0.7637(2) 1.02751(11) 0.0630 1.0000 Uani . . . . . .
F6 F 0.51643(10) 0.6958(3) 0.97216(12) 0.0811 1.0000 Uani . . . . . .
N6 N 0.70442(17) 0.8941(3) 0.96388(18) 0.0584 1.0000 Uani . . . . . .
C35 C 0.66435(16) 0.9161(3) 0.97174(14) 0.0381 1.0000 Uani . . . . . .
C36 C 0.61412(16) 0.9455(4) 0.98336(16) 0.0507 1.0000 Uani . . . . . .
H361 H 0.6180 1.0141 0.9990 0.0771 1.0000 Uiso R . . . . .
H362 H 0.5824 0.9421 0.9492 0.0769 1.0000 Uiso R . . . . .
H363 H 0.6075 0.8978 1.0097 0.0774 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.02954(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 . N1 . 2.144(2) yes
Ir1 . N3 . 2.126(2) yes
Ir1 . N4 . 2.050(2) yes
Ir1 . N5 . 2.044(2) yes
Ir1 . C21 . 1.998(2) yes
Ir1 . C33 . 2.012(3) yes
N1 . C1 . 1.350(3) yes
N1 . C5 . 1.343(3) yes
N2 . N3 . 1.385(3) yes
N2 . C5 . 1.405(3) yes
N2 . C6 . 1.373(3) yes
N3 . C8 . 1.325(3) yes
N4 . C11 . 1.345(3) yes
N4 . C15 . 1.367(3) yes
N5 . C23 . 1.344(3) yes
N5 . C27 . 1.359(3) yes
C1 . C2 . 1.378(4) yes
C1 . H11 . 0.930 no
C2 . C3 . 1.387(4) yes
C2 . H21 . 0.919 no
C3 . C4 . 1.381(4) yes
C3 . H31 . 0.921 no
C4 . C5 . 1.395(4) yes
C4 . H41 . 0.910 no
C6 . C7 . 1.364(4) yes
C6 . C9 . 1.490(4) yes
C7 . C8 . 1.405(4) yes
C7 . H71 . 0.923 no
C8 . C10 . 1.487(4) yes
C9 . H91 . 0.958 no
C9 . H92 . 0.945 no
C9 . H93 . 0.961 no
C10 . H101 . 0.961 no
C10 . H102 . 0.946 no
C10 . H103 . 0.948 no
C11 . C12 . 1.381(4) yes
C11 . H111 . 0.922 no
C12 . C13 . 1.387(4) yes
C12 . H121 . 0.915 no
C13 . C14 . 1.381(4) yes
C13 . H131 . 0.923 no
C14 . C15 . 1.385(4) yes
C14 . H141 . 0.936 no
C15 . C16 . 1.466(4) yes
C16 . C17 . 1.399(4) yes
C16 . C21 . 1.420(3) yes
C17 . C18 . 1.386(4) yes
C17 . H171 . 0.920 no
C18 . C19 . 1.390(4) yes
C18 . S1 . 1.759(3) yes
C19 . C20 . 1.386(4) yes
C19 . H191 . 0.916 no
C20 . C21 . 1.397(4) yes
C20 . H201 . 0.936 no
C22 . S1 . 1.769(3) yes
C23 . C24 . 1.377(4) yes
C23 . H231 . 0.927 no
C24 . C25 . 1.390(4) yes
C24 . H241 . 0.932 no
C25 . C26 . 1.384(4) yes
C25 . H251 . 0.927 no
C26 . C27 . 1.391(4) yes
C26 . H261 . 0.918 no
C27 . C28 . 1.470(3) yes
C28 . C29 . 1.394(4) yes
C28 . C33 . 1.415(4) yes
C29 . C30 . 1.394(4) yes
C29 . H291 . 0.925 no
C30 . C31 . 1.380(4) yes
C30 . S2 . 1.772(3) yes
C31 . C32 . 1.393(4) yes
C31 . H311 . 0.923 no
C32 . C33 . 1.403(4) yes
C32 . H321 . 0.932 no
C34 . S2 . 1.763(3) yes
S1 . O1 . 1.435(2) yes
S1 . O2 . 1.441(2) yes
S2 . O3 . 1.442(2) yes
S2 . O4 . 1.437(2) yes
P1 . F1 . 1.589(2) yes
P1 . F2 . 1.570(3) yes
P1 . F3 . 1.597(2) yes
P1 . F4 . 1.596(3) yes
P1 . F5 . 1.597(2) yes
P1 . F6 . 1.574(2) yes
N6 . C35 . 1.133(5) yes
C35 . C36 . 1.447(5) yes
C36 . H361 . 0.953 no
C36 . H362 . 0.952 no
C36 . H363 . 0.952 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 . Ir1 . N3 . 75.53(8) yes
N1 . Ir1 . N4 . 99.23(8) yes
N3 . Ir1 . N4 . 89.86(8) yes
N1 . Ir1 . N5 . 87.48(8) yes
N3 . Ir1 . N5 . 94.55(8) yes
N4 . Ir1 . N5 . 172.73(8) yes
N1 . Ir1 . C21 . 178.07(9) yes
N3 . Ir1 . C21 . 102.57(9) yes
N4 . Ir1 . C21 . 80.34(9) yes
N5 . Ir1 . C21 . 93.04(9) yes
N1 . Ir1 . C33 . 96.84(9) yes
N3 . Ir1 . C33 . 171.26(9) yes
N4 . Ir1 . C33 . 95.66(9) yes
N5 . Ir1 . C33 . 80.67(9) yes
C21 . Ir1 . C33 . 85.08(10) yes
Ir1 . N1 . C1 . 123.89(17) yes
Ir1 . N1 . C5 . 116.28(17) yes
C1 . N1 . C5 . 118.5(2) yes
N3 . N2 . C5 . 117.7(2) yes
N3 . N2 . C6 . 110.0(2) yes
C5 . N2 . C6 . 132.2(2) yes
Ir1 . N3 . N2 . 114.20(15) yes
Ir1 . N3 . C8 . 138.98(19) yes
N2 . N3 . C8 . 106.6(2) yes
Ir1 . N4 . C11 . 125.00(18) yes
Ir1 . N4 . C15 . 115.81(17) yes
C11 . N4 . C15 . 119.2(2) yes
Ir1 . N5 . C23 . 124.24(17) yes
Ir1 . N5 . C27 . 116.14(16) yes
C23 . N5 . C27 . 119.5(2) yes
N1 . C1 . C2 . 122.6(2) yes
N1 . C1 . H11 . 119.3 no
C2 . C1 . H11 . 118.0 no
C1 . C2 . C3 . 118.3(3) yes
C1 . C2 . H21 . 120.1 no
C3 . C2 . H21 . 121.7 no
C2 . C3 . C4 . 120.0(2) yes
C2 . C3 . H31 . 120.3 no
C4 . C3 . H31 . 119.7 no
C3 . C4 . C5 . 118.2(2) yes
C3 . C4 . H41 . 120.9 no
C5 . C4 . H41 . 120.8 no
N2 . C5 . C4 . 123.5(2) yes
N2 . C5 . N1 . 114.3(2) yes
C4 . C5 . N1 . 122.1(2) yes
N2 . C6 . C7 . 106.4(2) yes
N2 . C6 . C9 . 124.7(2) yes
C7 . C6 . C9 . 128.9(3) yes
C6 . C7 . C8 . 107.4(2) yes
C6 . C7 . H71 . 126.9 no
C8 . C7 . H71 . 125.7 no
C7 . C8 . N3 . 109.6(2) yes
C7 . C8 . C10 . 128.9(2) yes
N3 . C8 . C10 . 121.5(2) yes
C6 . C9 . H91 . 108.7 no
C6 . C9 . H92 . 109.6 no
H91 . C9 . H92 . 109.9 no
C6 . C9 . H93 . 109.3 no
H91 . C9 . H93 . 109.1 no
H92 . C9 . H93 . 110.2 no
C8 . C10 . H101 . 109.9 no
C8 . C10 . H102 . 110.0 no
H101 . C10 . H102 . 109.9 no
C8 . C10 . H103 . 110.3 no
H101 . C10 . H103 . 108.9 no
H102 . C10 . H103 . 107.8 no
N4 . C11 . C12 . 122.1(2) yes
N4 . C11 . H111 . 117.9 no
C12 . C11 . H111 . 120.0 no
C11 . C12 . C13 . 119.0(3) yes
C11 . C12 . H121 . 120.2 no
C13 . C12 . H121 . 120.8 no
C12 . C13 . C14 . 118.9(3) yes
C12 . C13 . H131 . 120.5 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 120.1(3) yes
C13 . C14 . H141 . 120.6 no
C15 . C14 . H141 . 119.3 no
C14 . C15 . N4 . 120.3(2) yes
C14 . C15 . C16 . 126.7(2) yes
N4 . C15 . C16 . 113.0(2) yes
C15 . C16 . C17 . 123.0(2) yes
C15 . C16 . C21 . 115.5(2) yes
C17 . C16 . C21 . 121.2(2) yes
C16 . C17 . C18 . 118.5(2) yes
C16 . C17 . H171 . 120.7 no
C18 . C17 . H171 . 120.8 no
C17 . C18 . C19 . 121.6(2) yes
C17 . C18 . S1 . 119.3(2) yes
C19 . C18 . S1 . 119.1(2) yes
C18 . C19 . C20 . 119.5(2) yes
C18 . C19 . H191 . 120.4 no
C20 . C19 . H191 . 120.1 no
C19 . C20 . C21 . 121.3(2) yes
C19 . C20 . H201 . 118.5 no
C21 . C20 . H201 . 120.2 no
C16 . C21 . C20 . 117.9(2) yes
C16 . C21 . Ir1 . 114.25(18) yes
C20 . C21 . Ir1 . 127.89(19) yes
N5 . C23 . C24 . 122.5(2) yes
N5 . C23 . H231 . 119.6 no
C24 . C23 . H231 . 117.9 no
C23 . C24 . C25 . 118.7(3) yes
C23 . C24 . H241 . 119.6 no
C25 . C24 . H241 . 121.6 no
C24 . C25 . C26 . 119.0(3) yes
C24 . C25 . H251 . 120.4 no
C26 . C25 . H251 . 120.7 no
C25 . C26 . C27 . 120.0(2) yes
C25 . C26 . H261 . 120.2 no
C27 . C26 . H261 . 119.8 no
C26 . C27 . N5 . 120.2(2) yes
C26 . C27 . C28 . 126.1(2) yes
N5 . C27 . C28 . 113.7(2) yes
C27 . C28 . C29 . 122.6(2) yes
C27 . C28 . C33 . 115.5(2) yes
C29 . C28 . C33 . 121.9(2) yes
C28 . C29 . C30 . 118.9(2) yes
C28 . C29 . H291 . 120.7 no
C30 . C29 . H291 . 120.3 no
C29 . C30 . C31 . 120.6(2) yes
C29 . C30 . S2 . 118.4(2) yes
C31 . C30 . S2 . 121.0(2) yes
C30 . C31 . C32 . 119.9(2) yes
C30 . C31 . H311 . 120.3 no
C32 . C31 . H311 . 119.8 no
C31 . C32 . C33 . 121.6(2) yes
C31 . C32 . H321 . 117.9 no
C33 . C32 . H321 . 120.5 no
C28 . C33 . C32 . 116.8(2) yes
C28 . C33 . Ir1 . 113.97(18) yes
C32 . C33 . Ir1 . 129.2(2) yes
C22 . S1 . C18 . 104.16(14) yes
C22 . S1 . O1 . 108.03(15) yes
C18 . S1 . O1 . 107.59(13) yes
C22 . S1 . O2 . 108.27(15) yes
C18 . S1 . O2 . 108.45(13) yes
O1 . S1 . O2 . 119.32(14) yes
C30 . S2 . C34 . 106.14(14) yes
C30 . S2 . O3 . 107.96(12) yes
C34 . S2 . O3 . 108.67(15) yes
C30 . S2 . O4 . 107.45(12) yes
C34 . S2 . O4 . 107.67(15) yes
O3 . S2 . O4 . 118.32(12) yes
F1 . P1 . F2 . 89.60(16) yes
F1 . P1 . F3 . 178.81(14) yes
F2 . P1 . F3 . 89.95(14) yes
F1 . P1 . F4 . 91.70(15) yes
F2 . P1 . F4 . 177.14(19) yes
F3 . P1 . F4 . 88.70(14) yes
F1 . P1 . F5 . 89.14(13) yes
F2 . P1 . F5 . 89.48(17) yes
F3 . P1 . F5 . 89.76(13) yes
F4 . P1 . F5 . 88.00(17) yes
F1 . P1 . F6 . 90.66(14) yes
F2 . P1 . F6 . 92.05(19) yes
F3 . P1 . F6 . 90.46(14) yes
F4 . P1 . F6 . 90.48(19) yes
F5 . P1 . F6 . 178.46(19) yes
N6 . C35 . C36 . 178.3(4) yes
C35 . C36 . H361 . 110.3 no
C35 . C36 . H362 . 110.2 no
H361 . C36 . H362 . 110.2 no
C35 . C36 . H363 . 109.9 no
H361 . C36 . H363 . 109.4 no
H362 . C36 . H363 . 106.9 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 . H41 . C9 . 121.95(9) 0.910 2.511 3.091(4) yes
C4 . H41 . O3 6_564 148.82(8) 0.910 2.457 3.270(4) yes
C11 . H111 . O4 7_546 149.45(8) 0.922 2.379 3.207(4) yes
C36 . H362 . O1 . 167.02(13) 0.952 2.305 3.239(4) yes


