# 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_p21n
_database_code_depnum_ccdc_archive 'CCDC 999587'
_audit_update_record             
;
2014-04-26 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N6'
_chemical_formula_sum            'C22 H20 N6'
_chemical_formula_weight         368.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.8574(10)
_cell_length_b                   9.1200(14)
_cell_length_c                   12.0577(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.478(10)
_cell_angle_gamma                90.00
_cell_volume                     906.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    855
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.32745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Mo Kα'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2106
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.1205
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1414
_reflns_number_gt                894
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0577P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1414
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0964
_refine_ls_R_factor_gt           0.0628
_refine_ls_wR_factor_ref         0.1659
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
N1 N 1.1760(3) 0.0647(3) 0.6217(2) 0.0187(7) Uani 1 1 d . . .
N2 N 0.6745(3) 0.7038(3) 0.5785(3) 0.0259(8) Uani 1 1 d . . .
N3 N 0.5163(3) 0.6521(3) 0.3917(2) 0.0212(8) Uani 1 1 d . . .
C1 C 1.0252(4) 0.0676(4) 0.5377(3) 0.0165(8) Uani 1 1 d . . .
C2 C 0.9215(4) 0.1859(4) 0.5224(3) 0.0174(8) Uani 1 1 d . . .
H1 H 0.8189 0.1837 0.4627 0.021 Uiso 1 1 calc R . .
C3 C 0.9704(4) 0.3083(4) 0.5962(3) 0.0167(8) Uani 1 1 d . . .
C4 C 1.1242(4) 0.3018(4) 0.6851(3) 0.0188(8) Uani 1 1 d . . .
H7 H 1.1617 0.3789 0.7387 0.023 Uiso 1 1 calc R . .
C5 C 1.2200(4) 0.1813(4) 0.6932(3) 0.0214(9) Uani 1 1 d . . .
H8 H 1.3228 0.1807 0.7526 0.026 Uiso 1 1 calc R . .
C6 C 0.8716(4) 0.4400(4) 0.5844(3) 0.0192(8) Uani 1 1 d . . .
H2 H 0.9069 0.5062 0.6474 0.023 Uiso 1 1 calc R . .
C7 C 0.7363(4) 0.4758(4) 0.4935(3) 0.0196(8) Uani 1 1 d . . .
H3 H 0.6983 0.4118 0.4292 0.023 Uiso 1 1 calc R . .
C8 C 0.6460(4) 0.6084(4) 0.4897(3) 0.0192(8) Uani 1 1 d . . .
C9 C 0.5593(4) 0.8102(4) 0.5347(3) 0.0277(10) Uani 1 1 d . . .
H6 H 0.5488 0.8921 0.5773 0.033 Uiso 1 1 calc R . .
C10 C 0.4624(4) 0.7801(4) 0.4206(3) 0.0247(9) Uani 1 1 d . . .
H5 H 0.3759 0.8363 0.3719 0.030 Uiso 1 1 calc R . .
C11 C 0.4465(4) 0.5739(4) 0.2791(3) 0.0252(9) Uani 1 1 d . . .
H4B H 0.3918 0.4875 0.2905 0.038 Uiso 1 1 calc R . .
H4C H 0.5312 0.5463 0.2514 0.038 Uiso 1 1 calc R . .
H4A H 0.3703 0.6363 0.2212 0.038 Uiso 1 1 calc R . .


_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
N1 C5 1.334(4) . ?
N1 C1 1.349(4) . ?
N2 C8 1.330(4) . ?
N2 C9 1.366(4) . ?
N3 C10 1.355(4) . ?
N3 C8 1.371(4) . ?
N3 C11 1.455(4) . ?
C1 C2 1.386(4) . ?
C1 C1 1.498(7) 3_756 ?
C2 C3 1.394(5) . ?
C2 H1 0.9300 . ?
C3 C4 1.392(4) . ?
C3 C6 1.462(4) . ?
C4 C5 1.371(5) . ?
C4 H7 0.9300 . ?
C5 H8 0.9300 . ?
C6 C7 1.335(5) . ?
C6 H2 0.9300 . ?
C7 C8 1.442(5) . ?
C7 H3 0.9300 . ?
C9 C10 1.356(5) . ?
C9 H6 0.9300 . ?
C10 H5 0.9300 . ?
C11 H4B 0.9600 . ?
C11 H4C 0.9600 . ?
C11 H4A 0.9600 . ?

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
C5 N1 C1 116.4(3) . . ?
C8 N2 C9 105.0(3) . . ?
C10 N3 C8 106.9(3) . . ?
C10 N3 C11 126.4(3) . . ?
C8 N3 C11 126.7(3) . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 C1 115.6(4) . 3_756 ?
C2 C1 C1 121.6(4) . 3_756 ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H1 119.9 . . ?
C3 C2 H1 119.9 . . ?
C4 C3 C2 116.5(3) . . ?
C4 C3 C6 119.4(3) . . ?
C2 C3 C6 124.1(3) . . ?
C5 C4 C3 119.6(3) . . ?
C5 C4 H7 120.2 . . ?
C3 C4 H7 120.2 . . ?
N1 C5 C4 124.5(3) . . ?
N1 C5 H8 117.7 . . ?
C4 C5 H8 117.7 . . ?
C7 C6 C3 127.3(3) . . ?
C7 C6 H2 116.3 . . ?
C3 C6 H2 116.3 . . ?
C6 C7 C8 123.5(3) . . ?
C6 C7 H3 118.2 . . ?
C8 C7 H3 118.2 . . ?
N2 C8 N3 110.9(3) . . ?
N2 C8 C7 125.7(3) . . ?
N3 C8 C7 123.4(3) . . ?
C10 C9 N2 110.7(3) . . ?
C10 C9 H6 124.6 . . ?
N2 C9 H6 124.6 . . ?
N3 C10 C9 106.5(3) . . ?
N3 C10 H5 126.8 . . ?
C9 C10 H5 126.8 . . ?
N3 C11 H4B 109.5 . . ?
N3 C11 H4C 109.5 . . ?
H4B C11 H4C 109.5 . . ?
N3 C11 H4A 109.5 . . ?
H4B C11 H4A 109.5 . . ?
H4C C11 H4A 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.885
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.885
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_pgb
_database_code_depnum_ccdc_archive 'CCDC 999588'
_audit_update_record             
;
2014-04-26 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H36 Ir N8, 4(C H Cl3), Cl'
_chemical_formula_sum            'C48 H40 Cl13 Ir N8'
_chemical_formula_weight         1381.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   10.188(9)
_cell_length_b                   31.26(3)
_cell_length_c                   17.715(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.279(15)
_cell_angle_gamma                90.00
_cell_volume                     5443(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    786
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      17.83

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.687
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2728
_exptl_absorpt_coefficient_mu    3.135
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.357
_exptl_absorpt_correction_T_max  0.601
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12296
_diffrn_reflns_av_R_equivalents  0.1357
_diffrn_reflns_av_sigmaI/netI    0.1185
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         18.11
_reflns_number_total             3718
_reflns_number_gt                2408
_reflns_threshold_expression     >2sigma(I)

_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'

_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)+(0.0945P)²+42.8709P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3718
_refine_ls_number_parameters     333
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0678
_refine_ls_wR_factor_ref         0.1988
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.020
_refine_ls_shift/su_mean         0.001

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 0.26248(10) 0.62746(3) 0.48810(5) 0.0341(5) Uani 1 1 d . . .
N1 N 0.1258(18) 0.6275(6) 0.5460(10) 0.0373(18) Uani 1 1 d . . .
N2 N 0.4070(19) 0.6204(5) 0.4304(10) 0.0373(18) Uani 1 1 d . . .
N3 N 0.3747(19) 0.6811(5) 0.5458(10) 0.0373(18) Uani 1 1 d . . .
N4 N 0.1654(19) 0.6810(5) 0.4225(10) 0.0373(18) Uani 1 1 d . . .
N5 N 0.7723(19) 0.8617(5) 0.7220(10) 0.0373(18) Uani 1 1 d . . .
N6 N 0.6749(19) 0.9037(5) 0.6210(10) 0.0373(18) Uani 1 1 d . . .
N7 N -0.2497(19) 0.8601(5) 0.2649(10) 0.0373(18) Uani 1 1 d . . .
N8 N -0.1583(19) 0.8983(5) 0.3721(10) 0.0373(18) Uani 1 1 d . . .
C1 C 0.105(2) 0.6555(7) 0.6017(13) 0.043(2) Uani 1 1 d . . .
H1 H 0.1667 0.6780 0.6154 0.052 Uiso 1 1 calc R . .
C2 C 0.004(2) 0.6538(7) 0.6387(14) 0.043(2) Uani 1 1 d . . .
H2 H -0.0005 0.6742 0.6761 0.052 Uiso 1 1 calc R . .
C3 C -0.088(2) 0.6227(7) 0.6210(13) 0.043(2) Uani 1 1 d . . .
H3 H -0.1566 0.6209 0.6468 0.052 Uiso 1 1 calc R . .
C4 C -0.082(2) 0.5929(7) 0.5643(13) 0.043(2) Uani 1 1 d . . .
H4 H -0.1439 0.5704 0.5522 0.052 Uiso 1 1 calc R . .
C5 C 0.023(2) 0.5984(7) 0.5247(14) 0.043(2) Uani 1 1 d . . .
C6 C 0.036(2) 0.5688(7) 0.4605(14) 0.043(2) Uani 1 1 d . . .
C7 C -0.051(2) 0.5354(7) 0.4302(13) 0.043(2) Uani 1 1 d . . .
H7 H -0.1226 0.5287 0.4514 0.052 Uiso 1 1 calc R . .
C8 C -0.031(2) 0.5124(7) 0.3691(13) 0.043(2) Uani 1 1 d . . .
H8 H -0.0892 0.4901 0.3481 0.052 Uiso 1 1 calc R . .
C9 C 0.074(2) 0.5219(7) 0.3387(14) 0.043(2) Uani 1 1 d . . .
H9 H 0.0880 0.5055 0.2977 0.052 Uiso 1 1 calc R . .
C10 C 0.163(2) 0.5558(7) 0.3672(13) 0.043(2) Uani 1 1 d . . .
H10 H 0.2340 0.5618 0.3445 0.052 Uiso 1 1 calc R . .
C11 C 0.147(2) 0.5804(7) 0.4292(14) 0.043(2) Uani 1 1 d . . .
C12 C 0.422(2) 0.6420(7) 0.3681(14) 0.042(2) Uani 1 1 d . . .
H12 H 0.3624 0.6645 0.3507 0.050 Uiso 1 1 calc R . .
C13 C 0.515(2) 0.6346(7) 0.3280(14) 0.042(2) Uani 1 1 d . . .
H13 H 0.5158 0.6504 0.2836 0.050 Uiso 1 1 calc R . .
C14 C 0.610(2) 0.6023(7) 0.3558(13) 0.042(2) Uani 1 1 d . . .
H14 H 0.6783 0.5964 0.3314 0.050 Uiso 1 1 calc R . .
C15 C 0.600(2) 0.5796(7) 0.4194(13) 0.042(2) Uani 1 1 d . . .
H15 H 0.6608 0.5574 0.4372 0.050 Uiso 1 1 calc R . .
C16 C 0.502(3) 0.5882(7) 0.4586(14) 0.042(2) Uani 1 1 d . . .
C17 C 0.485(3) 0.5675(7) 0.5263(14) 0.042(2) Uani 1 1 d . . .
C18 C 0.568(2) 0.5349(7) 0.5667(13) 0.042(2) Uani 1 1 d . . .
H18 H 0.6428 0.5261 0.5496 0.050 Uiso 1 1 calc R . .
C19 C 0.543(2) 0.5158(7) 0.6311(13) 0.042(2) Uani 1 1 d . . .
H19 H 0.6002 0.4941 0.6564 0.050 Uiso 1 1 calc R . .
C20 C 0.434(2) 0.5282(7) 0.6593(14) 0.042(2) Uani 1 1 d . . .
H20 H 0.4203 0.5158 0.7043 0.050 Uiso 1 1 calc R . .
C21 C 0.346(3) 0.5599(7) 0.6186(13) 0.042(2) Uani 1 1 d . . .
H21 H 0.2712 0.5680 0.6359 0.050 Uiso 1 1 calc R . .
C22 C 0.369(3) 0.5790(7) 0.5538(14) 0.042(2) Uani 1 1 d . . .
C23 C 0.483(2) 0.6780(7) 0.6057(13) 0.034(2) Uani 1 1 d . . .
H23 H 0.5071 0.6511 0.6272 0.041 Uiso 1 1 calc R . .
C24 C 0.561(2) 0.7121(6) 0.6378(13) 0.034(2) Uani 1 1 d . . .
H24 H 0.6391 0.7079 0.6784 0.041 Uiso 1 1 calc R . .
C25 C 0.523(2) 0.7539(7) 0.6093(13) 0.034(2) Uani 1 1 d . . .
C26 C 0.405(2) 0.7560(7) 0.5472(12) 0.034(2) Uani 1 1 d . . .
H26 H 0.3731 0.7825 0.5261 0.041 Uiso 1 1 calc R . .
C27 C 0.336(2) 0.7203(7) 0.5177(13) 0.034(2) Uani 1 1 d . . .
C28 C 0.212(2) 0.7205(7) 0.4512(13) 0.034(2) Uani 1 1 d . . .
C29 C 0.142(2) 0.7567(7) 0.4175(12) 0.034(2) Uani 1 1 d . . .
H29 H 0.1723 0.7836 0.4364 0.041 Uiso 1 1 calc R . .
C30 C 0.027(2) 0.7531(7) 0.3569(13) 0.034(2) Uani 1 1 d . . .
C31 C -0.016(2) 0.7135(6) 0.3273(13) 0.034(2) Uani 1 1 d . . .
H31 H -0.0909 0.7106 0.2845 0.041 Uiso 1 1 calc R . .
C32 C 0.053(2) 0.6793(7) 0.3609(12) 0.034(2) Uani 1 1 d . . .
H32 H 0.0217 0.6525 0.3412 0.041 Uiso 1 1 calc R . .
C33 C 0.607(3) 0.7896(7) 0.6455(15) 0.053(3) Uani 1 1 d . . .
H33 H 0.6769 0.7843 0.6903 0.064 Uiso 1 1 calc R . .
C34 C 0.590(3) 0.8301(7) 0.6183(15) 0.053(3) Uani 1 1 d . . .
H34 H 0.5206 0.8358 0.5738 0.064 Uiso 1 1 calc R . .
C35 C 0.676(3) 0.8647(7) 0.6557(15) 0.053(3) Uani 1 1 d . . .
C36 C 0.832(3) 0.9009(7) 0.7324(15) 0.053(3) Uani 1 1 d . . .
H36 H 0.9024 0.9088 0.7752 0.064 Uiso 1 1 calc R . .
C37 C 0.775(3) 0.9263(8) 0.6723(14) 0.053(3) Uani 1 1 d . . .
H37 H 0.7984 0.9546 0.6663 0.064 Uiso 1 1 calc R . .
C38 C 0.594(3) 0.9167(7) 0.5468(14) 0.053(3) Uani 1 1 d . . .
H38A H 0.6441 0.9124 0.5084 0.079 Uiso 1 1 calc R . .
H38B H 0.5718 0.9464 0.5486 0.079 Uiso 1 1 calc R . .
H38C H 0.5122 0.9000 0.5331 0.079 Uiso 1 1 calc R . .
C39 C -0.060(2) 0.7906(7) 0.3265(13) 0.040(3) Uani 1 1 d . . .
H39 H -0.1236 0.7877 0.2783 0.048 Uiso 1 1 calc R . .
C40 C -0.054(2) 0.8279(7) 0.3627(13) 0.040(3) Uani 1 1 d . . .
H40 H 0.0135 0.8330 0.4084 0.048 Uiso 1 1 calc R . .
C41 C -0.155(2) 0.8607(7) 0.3309(14) 0.040(3) Uani 1 1 d . . .
C42 C -0.319(2) 0.8972(7) 0.2642(13) 0.040(3) Uani 1 1 d . . .
H42 H -0.3942 0.9055 0.2245 0.048 Uiso 1 1 calc R . .
C43 C -0.265(2) 0.9198(7) 0.3270(13) 0.040(3) Uani 1 1 d . . .
H43 H -0.2957 0.9463 0.3387 0.048 Uiso 1 1 calc R . .
C44 C -0.076(2) 0.9104(7) 0.4489(12) 0.040(3) Uani 1 1 d . . .
H44A H -0.0651 0.9409 0.4514 0.060 Uiso 1 1 calc R . .
H44B H 0.0120 0.8971 0.4583 0.060 Uiso 1 1 calc R . .
H44C H -0.1195 0.9012 0.4879 0.060 Uiso 1 1 calc R . .
C45 C 0.128(3) 0.6927(7) 0.1317(15) 0.053(3) Uani 1 1 d . . .
H45 H 0.1773 0.6850 0.0931 0.064 Uiso 1 1 calc R . .
C46 C 0.269(3) 0.5770(7) 0.8509(15) 0.053(3) Uani 1 1 d . . .
H46 H 0.2695 0.5887 0.9023 0.064 Uiso 1 1 calc R . .
C47 C 0.766(3) 0.0500(7) 0.3964(14) 0.053(3) Uani 1 1 d . . .
H47 H 0.7811 0.0792 0.4168 0.064 Uiso 1 1 calc R . .
C48 C 0.604(3) 0.7855(7) 0.3686(15) 0.053(3) Uani 1 1 d . . .
H48 H 0.6341 0.8005 0.3275 0.064 Uiso 1 1 calc R . .
Cl1 Cl 0.2571(6) 0.64006(16) 0.0030(3) 0.0365(16) Uani 1 1 d . . .
Cl2 Cl -0.0137(11) 0.7204(4) 0.0863(6) 0.145(4) Uani 1 1 d . . .
Cl3 Cl 0.0933(14) 0.6473(3) 0.1765(6) 0.148(5) Uani 1 1 d . . .
Cl4 Cl 0.2311(10) 0.7260(3) 0.2027(5) 0.106(3) Uani 1 1 d . . .
Cl5 Cl 0.1141(10) 0.5582(4) 0.8092(7) 0.163(6) Uani 1 1 d . . .
Cl6 Cl 0.3976(8) 0.5403(2) 0.8630(4) 0.077(2) Uani 1 1 d . . .
Cl7 Cl 0.3072(16) 0.6197(3) 0.7915(6) 0.175(6) Uani 1 1 d . . .
Cl8 Cl 0.7349(8) 0.0171(2) 0.4708(4) 0.073(2) Uani 1 1 d . . .
Cl9 Cl 0.9056(8) 0.0347(2) 0.3700(5) 0.074(2) Uani 1 1 d . . .
Cl10 Cl 0.6171(8) 0.0502(2) 0.3156(4) 0.075(2) Uani 1 1 d . . .
Cl11 Cl 0.6540(13) 0.8123(3) 0.4476(6) 0.140(4) Uani 1 1 d . . .
Cl12 Cl 0.4363(17) 0.7771(8) 0.3364(8) 0.314(13) Uani 1 1 d . . .
Cl13 Cl 0.659(2) 0.7364(4) 0.3724(16) 0.340(15) Uani 1 1 d . . .


_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 N1 1.936(18) . ?
Ir1 C11 2.00(2) . ?
Ir1 N2 2.014(19) . ?
Ir1 C22 2.04(2) . ?
Ir1 N4 2.127(17) . ?
Ir1 N3 2.132(18) . ?
N1 C5 1.37(3) . ?
N1 C1 1.38(3) . ?
N2 C12 1.34(2) . ?
N2 C16 1.39(3) . ?
N3 C23 1.32(2) . ?
N3 C27 1.34(2) . ?
N4 C32 1.36(2) . ?
N4 C28 1.37(2) . ?
N5 C35 1.32(3) . ?
N5 C36 1.36(3) . ?
N6 C35 1.36(3) . ?
N6 C37 1.37(3) . ?
N6 C38 1.41(3) . ?
N7 C41 1.30(3) . ?
N7 C42 1.36(2) . ?
N8 C43 1.35(2) . ?
N8 C41 1.39(3) . ?
N8 C44 1.45(2) . ?
C1 C2 1.36(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.33(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.38(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.44(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.50(3) . ?
C6 C7 1.39(3) . ?
C6 C11 1.42(3) . ?
C7 C8 1.36(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.35(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.40(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.39(3) . ?
C10 H10 0.9300 . ?
C12 C13 1.34(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.40(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.36(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.38(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.42(3) . ?
C17 C18 1.40(3) . ?
C17 C22 1.43(3) . ?
C18 C19 1.37(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.38(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.40(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.37(3) . ?
C21 H21 0.9300 . ?
C23 C24 1.36(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.42(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.40(3) . ?
C25 C33 1.45(3) . ?
C26 C27 1.35(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.48(3) . ?
C28 C29 1.39(3) . ?
C29 C30 1.36(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.37(3) . ?
C30 C39 1.49(3) . ?
C31 C32 1.33(3) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.35(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.44(3) . ?
C34 H34 0.9300 . ?
C36 C37 1.33(3) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 C40 1.32(3) . ?
C39 H39 0.9300 . ?
C40 C41 1.45(3) . ?
C40 H40 0.9300 . ?
C42 C43 1.31(3) . ?
C42 H42 0.9300 . ?
C43 H43 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C45 Cl2 1.69(3) . ?
C45 Cl3 1.71(2) . ?
C45 Cl4 1.75(2) . ?
C45 H45 0.9800 . ?
C46 Cl5 1.66(3) . ?
C46 Cl6 1.71(2) . ?
C46 Cl7 1.80(2) . ?
C46 H46 0.9800 . ?
C47 Cl9 1.68(2) . ?
C47 Cl8 1.77(2) . ?
C47 Cl10 1.79(3) . ?
C47 H47 0.9800 . ?
C48 Cl11 1.59(2) . ?
C48 Cl13 1.63(3) . ?
C48 Cl12 1.67(3) . ?
C48 H48 0.9800 . ?

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
N1 Ir1 C11 82.5(9) . . ?
N1 Ir1 N2 173.6(7) . . ?
C11 Ir1 N2 93.7(8) . . ?
N1 Ir1 C22 92.7(8) . . ?
C11 Ir1 C22 84.5(9) . . ?
N2 Ir1 C22 81.8(8) . . ?
N1 Ir1 N4 89.6(7) . . ?
C11 Ir1 N4 99.7(8) . . ?
N2 Ir1 N4 96.1(7) . . ?
C22 Ir1 N4 175.4(8) . . ?
N1 Ir1 N3 96.6(7) . . ?
C11 Ir1 N3 175.5(8) . . ?
N2 Ir1 N3 87.6(7) . . ?
C22 Ir1 N3 99.9(8) . . ?
N4 Ir1 N3 75.9(7) . . ?
C5 N1 C1 112(2) . . ?
C5 N1 Ir1 117.4(15) . . ?
C1 N1 Ir1 130.3(17) . . ?
C12 N2 C16 116(2) . . ?
C12 N2 Ir1 128.5(17) . . ?
C16 N2 Ir1 115.4(15) . . ?
C23 N3 C27 118(2) . . ?
C23 N3 Ir1 124.0(15) . . ?
C27 N3 Ir1 118.2(15) . . ?
C32 N4 C28 118.1(19) . . ?
C32 N4 Ir1 125.4(15) . . ?
C28 N4 Ir1 116.1(14) . . ?
C35 N5 C36 105(2) . . ?
C35 N6 C37 104(2) . . ?
C35 N6 C38 128(2) . . ?
C37 N6 C38 128(2) . . ?
C41 N7 C42 104.8(19) . . ?
C43 N8 C41 103.7(18) . . ?
C43 N8 C44 127.2(18) . . ?
C41 N8 C44 128.8(19) . . ?
C2 C1 N1 127(2) . . ?
C2 C1 H1 116.6 . . ?
N1 C1 H1 116.6 . . ?
C3 C2 C1 120(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120(2) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 117(2) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
N1 C5 C4 124(2) . . ?
N1 C5 C6 114(2) . . ?
C4 C5 C6 122(2) . . ?
C7 C6 C11 122(2) . . ?
C7 C6 C5 125(2) . . ?
C11 C6 C5 112(2) . . ?
C8 C7 C6 119(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C9 C8 C7 120(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 122(2) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 H9 119.0 . . ?
C11 C10 C9 120(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C6 116(2) . . ?
C10 C11 Ir1 129.9(19) . . ?
C6 C11 Ir1 113.6(17) . . ?
N2 C12 C13 127(2) . . ?
N2 C12 H12 116.5 . . ?
C13 C12 H12 116.5 . . ?
C12 C13 C14 117(2) . . ?
C12 C13 H13 121.5 . . ?
C14 C13 H13 121.5 . . ?
C15 C14 C13 118(2) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 123(2) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 H15 118.7 . . ?
C15 C16 N2 119(2) . . ?
C15 C16 C17 127(2) . . ?
N2 C16 C17 114(2) . . ?
C18 C17 C16 125(2) . . ?
C18 C17 C22 117(2) . . ?
C16 C17 C22 118(2) . . ?
C19 C18 C17 121(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 121(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C21 119(2) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C22 C21 C20 121(2) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C21 C22 C17 121(2) . . ?
C21 C22 Ir1 128.3(19) . . ?
C17 C22 Ir1 110.8(17) . . ?
N3 C23 C24 124(2) . . ?
N3 C23 H23 118.2 . . ?
C24 C23 H23 118.2 . . ?
C23 C24 C25 120(2) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C26 C25 C24 115(2) . . ?
C26 C25 C33 127(2) . . ?
C24 C25 C33 119(2) . . ?
C27 C26 C25 121(2) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
N3 C27 C26 123(2) . . ?
N3 C27 C28 114(2) . . ?
C26 C27 C28 123(2) . . ?
N4 C28 C29 119(2) . . ?
N4 C28 C27 115.5(19) . . ?
C29 C28 C27 126(2) . . ?
C30 C29 C28 121(2) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 120(2) . . ?
C29 C30 C39 122(2) . . ?
C31 C30 C39 118(2) . . ?
C32 C31 C30 119(2) . . ?
C32 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
C31 C32 N4 124(2) . . ?
C31 C32 H32 118.0 . . ?
N4 C32 H32 118.0 . . ?
C34 C33 C25 124(2) . . ?
C34 C33 H33 118.0 . . ?
C25 C33 H33 118.0 . . ?
C33 C34 C35 122(3) . . ?
C33 C34 H34 118.8 . . ?
C35 C34 H34 118.8 . . ?
N5 C35 N6 112(2) . . ?
N5 C35 C34 125(2) . . ?
N6 C35 C34 122(2) . . ?
C37 C36 N5 110(2) . . ?
C37 C36 H36 125.0 . . ?
N5 C36 H36 125.0 . . ?
C36 C37 N6 108(2) . . ?
C36 C37 H37 125.8 . . ?
N6 C37 H37 125.8 . . ?
N6 C38 H38A 109.5 . . ?
N6 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
N6 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C40 C39 C30 125(2) . . ?
C40 C39 H39 117.5 . . ?
C30 C39 H39 117.5 . . ?
C39 C40 C41 120(2) . . ?
C39 C40 H40 120.1 . . ?
C41 C40 H40 120.1 . . ?
N7 C41 N8 112(2) . . ?
N7 C41 C40 128(2) . . ?
N8 C41 C40 120(2) . . ?
C43 C42 N7 111(2) . . ?
C43 C42 H42 124.7 . . ?
N7 C42 H42 124.7 . . ?
C42 C43 N8 109(2) . . ?
C42 C43 H43 125.4 . . ?
N8 C43 H43 125.4 . . ?
N8 C44 H44A 109.5 . . ?
N8 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
N8 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
Cl2 C45 Cl3 113.1(16) . . ?
Cl2 C45 Cl4 108.2(13) . . ?
Cl3 C45 Cl4 108.6(14) . . ?
Cl2 C45 H45 109.0 . . ?
Cl3 C45 H45 109.0 . . ?
Cl4 C45 H45 109.0 . . ?
Cl5 C46 Cl6 115.1(14) . . ?
Cl5 C46 Cl7 109.1(16) . . ?
Cl6 C46 Cl7 107.1(14) . . ?
Cl5 C46 H46 108.5 . . ?
Cl6 C46 H46 108.5 . . ?
Cl7 C46 H46 108.5 . . ?
Cl9 C47 Cl8 112.0(14) . . ?
Cl9 C47 Cl10 112.4(13) . . ?
Cl8 C47 Cl10 108.5(13) . . ?
Cl9 C47 H47 107.9 . . ?
Cl8 C47 H47 107.9 . . ?
Cl10 C47 H47 107.9 . . ?
Cl11 C48 Cl13 115.6(19) . . ?
Cl11 C48 Cl12 116.3(17) . . ?
Cl13 C48 Cl12 99.9(17) . . ?
Cl11 C48 H48 108.2 . . ?
Cl13 C48 H48 108.2 . . ?
Cl12 C48 H48 108.2 . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        18.11
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         1.579
_refine_diff_density_min         -1.099
_refine_diff_density_rms         0.157
####################################################################### 
# 
# 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_ss
_database_code_depnum_ccdc_archive 'CCDC 999589'
_audit_update_record             
;
2014-04-26 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C50 H40 Ir N4 O2, F6 P, C H2 Cl2'
_chemical_formula_sum            'C51 H42 Cl2 F6 Ir N4 O2 P'
_chemical_formula_weight         1150.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.773(6)
_cell_length_b                   13.362(4)
_cell_length_c                   20.727(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.386(6)
_cell_angle_gamma                90.00
_cell_volume                     5130(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    1273
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      16.15

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2288
_exptl_absorpt_coefficient_mu    2.802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.498
_exptl_absorpt_correction_T_max  0.799
_exptl_absorpt_process_details   'SADABS; BRUKER, 2008'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36450
_diffrn_reflns_av_R_equivalents  0.1579
_diffrn_reflns_av_sigmaI/netI    0.1857
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.14
_reflns_number_total             8987
_reflns_number_gt                4470
_reflns_threshold_expression     >2sigma(I)

_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'

_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)+(0.0723P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8987
_refine_ls_number_parameters     606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1464
_refine_ls_R_factor_gt           0.0679
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.12614(2) 0.22012(3) 0.24019(2) 0.03363(17) Uani 1 1 d . . .
N1 N 0.1581(5) 0.3128(7) 0.3171(5) 0.044(3) Uani 1 1 d . . .
N2 N 0.1001(5) 0.1125(7) 0.1697(5) 0.035(3) Uani 1 1 d . . .
N3 N 0.1300(5) 0.3414(7) 0.1728(4) 0.033(2) Uani 1 1 d . . .
N4 N 0.0169(5) 0.2726(7) 0.2200(5) 0.041(2) Uani 1 1 d . . .
C1 C 0.1146(7) 0.3742(10) 0.3463(7) 0.050(4) Uani 1 1 d . . .
H1 H 0.0658 0.3765 0.3287 0.060 Uiso 1 1 calc R . .
C2 C 0.1377(9) 0.4317(12) 0.3991(8) 0.073(5) Uani 1 1 d . . .
H2 H 0.1056 0.4697 0.4187 0.088 Uiso 1 1 calc R . .
C3 C 0.2104(9) 0.4321(10) 0.4226(7) 0.067(4) Uani 1 1 d . . .
H3 H 0.2281 0.4729 0.4580 0.080 Uiso 1 1 calc R . .
C4 C 0.2578(8) 0.3730(10) 0.3951(7) 0.064(4) Uani 1 1 d . . .
H4 H 0.3069 0.3744 0.4116 0.076 Uiso 1 1 calc R . .
C5 C 0.2317(7) 0.3114(8) 0.3423(6) 0.041(3) Uani 1 1 d . . .
C6 C 0.2729(6) 0.2420(8) 0.3091(6) 0.037(3) Uani 1 1 d . . .
C7 C 0.3468(6) 0.2257(9) 0.3260(7) 0.049(4) Uani 1 1 d . . .
H7 H 0.3728 0.2593 0.3615 0.059 Uiso 1 1 calc R . .
C8 C 0.3817(6) 0.1607(9) 0.2907(7) 0.048(4) Uani 1 1 d . . .
H8 H 0.4312 0.1517 0.3025 0.057 Uiso 1 1 calc R . .
C9 C 0.3448(6) 0.1078(9) 0.2377(7) 0.053(4) Uani 1 1 d . . .
H9 H 0.3695 0.0653 0.2135 0.063 Uiso 1 1 calc R . .
C10 C 0.2700(6) 0.1197(8) 0.2214(6) 0.044(3) Uani 1 1 d . . .
H10 H 0.2448 0.0827 0.1871 0.053 Uiso 1 1 calc R . .
C11 C 0.2318(5) 0.1873(8) 0.2563(6) 0.031(3) Uani 1 1 d . . .
C12 C 0.0999(6) 0.1267(9) 0.1039(6) 0.037(3) Uani 1 1 d . . .
H12 H 0.1132 0.1885 0.0890 0.044 Uiso 1 1 calc R . .
C13 C 0.0806(6) 0.0516(9) 0.0603(6) 0.039(3) Uani 1 1 d . . .
H13 H 0.0832 0.0611 0.0163 0.047 Uiso 1 1 calc R . .
C14 C 0.0564(6) -0.0412(8) 0.0819(7) 0.041(3) Uani 1 1 d . . .
H14 H 0.0408 -0.0922 0.0524 0.049 Uiso 1 1 calc R . .
C15 C 0.0566(5) -0.0537(8) 0.1478(6) 0.036(3) Uani 1 1 d . . .
H15 H 0.0393 -0.1134 0.1624 0.043 Uiso 1 1 calc R . .
C16 C 0.0820(5) 0.0205(8) 0.1940(6) 0.035(3) Uani 1 1 d . . .
C17 C 0.0925(5) 0.0145(8) 0.2652(6) 0.030(3) Uani 1 1 d . . .
C18 C 0.0854(6) -0.0777(8) 0.2966(6) 0.038(3) Uani 1 1 d . . .
H18 H 0.0731 -0.1360 0.2729 0.045 Uiso 1 1 calc R . .
C19 C 0.0975(6) -0.0778(9) 0.3636(7) 0.042(3) Uani 1 1 d . . .
H19 H 0.0934 -0.1376 0.3856 0.050 Uiso 1 1 calc R . .
C20 C 0.1156(6) 0.0089(9) 0.3995(6) 0.045(3) Uani 1 1 d . . .
H20 H 0.1218 0.0078 0.4450 0.054 Uiso 1 1 calc R . .
C21 C 0.1242(6) 0.0982(8) 0.3661(7) 0.042(4) Uani 1 1 d . . .
H21 H 0.1373 0.1561 0.3900 0.051 Uiso 1 1 calc R . .
C22 C 0.1136(6) 0.1030(8) 0.2970(6) 0.030(3) Uani 1 1 d . . .
C23 C 0.1896(6) 0.3771(9) 0.1524(6) 0.040(3) Uani 1 1 d . . .
H23 H 0.2337 0.3484 0.1696 0.048 Uiso 1 1 calc R . .
C24 C 0.1893(7) 0.4521(9) 0.1085(6) 0.044(3) Uani 1 1 d . . .
H24 H 0.2321 0.4721 0.0952 0.053 Uiso 1 1 calc R . .
C25 C 0.1249(6) 0.4991(8) 0.0835(6) 0.036(3) Uani 1 1 d . . .
C26 C 0.0622(6) 0.4639(8) 0.1056(6) 0.033(3) Uani 1 1 d . . .
H26 H 0.0180 0.4931 0.0892 0.040 Uiso 1 1 calc R . .
C27 C 0.0644(6) 0.3860(7) 0.1517(6) 0.031(3) Uani 1 1 d . . .
C28 C 0.0026(6) 0.3507(8) 0.1776(6) 0.037(3) Uani 1 1 d . . .
C29 C -0.0656(6) 0.3919(8) 0.1647(6) 0.041(3) Uani 1 1 d . . .
H29 H -0.0738 0.4459 0.1361 0.050 Uiso 1 1 calc R . .
C30 C -0.1230(6) 0.3547(8) 0.1933(6) 0.044(3) Uani 1 1 d . . .
C31 C -0.1067(6) 0.2736(10) 0.2344(7) 0.055(4) Uani 1 1 d . . .
H31 H -0.1429 0.2443 0.2538 0.066 Uiso 1 1 calc R . .
C32 C -0.0388(6) 0.2362(9) 0.2470(7) 0.049(4) Uani 1 1 d . . .
H32 H -0.0300 0.1826 0.2758 0.059 Uiso 1 1 calc R . .
C33 C 0.1194(6) 0.5826(8) 0.0384(6) 0.040(3) Uani 1 1 d . . .
H33 H 0.0732 0.6068 0.0233 0.048 Uiso 1 1 calc R . .
C34 C 0.1738(6) 0.6283(8) 0.0164(6) 0.042(3) Uani 1 1 d . . .
H34 H 0.2188 0.5988 0.0284 0.050 Uiso 1 1 calc R . .
C35 C 0.1730(6) 0.7182(9) -0.0240(5) 0.039(3) Uani 1 1 d . . .
C36 C 0.1109(6) 0.7739(10) -0.0422(6) 0.047(3) Uani 1 1 d . . .
H36 H 0.0680 0.7532 -0.0293 0.056 Uiso 1 1 calc R . .
C37 C 0.1113(7) 0.8606(9) -0.0797(6) 0.045(3) Uani 1 1 d . . .
H37 H 0.0691 0.8969 -0.0922 0.055 Uiso 1 1 calc R . .
C38 C 0.1760(7) 0.8921(9) -0.0982(7) 0.054(4) Uani 1 1 d . . .
H38 H 0.1764 0.9499 -0.1231 0.065 Uiso 1 1 calc R . .
C39 C 0.2383(7) 0.8397(10) -0.0806(7) 0.057(4) Uani 1 1 d . . .
H39 H 0.2814 0.8615 -0.0926 0.068 Uiso 1 1 calc R . .
C40 C 0.2357(6) 0.7521(9) -0.0441(7) 0.047(4) Uani 1 1 d . . .
C41 C 0.3626(6) 0.7177(10) -0.0471(7) 0.057(4) Uani 1 1 d . . .
H41A H 0.3556 0.7118 -0.0939 0.086 Uiso 1 1 calc R . .
H41B H 0.3997 0.6721 -0.0281 0.086 Uiso 1 1 calc R . .
H41C H 0.3767 0.7849 -0.0347 0.086 Uiso 1 1 calc R . .
C42 C -0.1989(6) 0.3941(9) 0.1831(6) 0.049(4) Uani 1 1 d . . .
H42 H -0.2314 0.3652 0.2069 0.058 Uiso 1 1 calc R . .
C43 C -0.2228(7) 0.4699(9) 0.1410(7) 0.052(4) Uani 1 1 d . . .
H43 H -0.1891 0.4978 0.1180 0.062 Uiso 1 1 calc R . .
C44 C -0.2957(6) 0.5119(9) 0.1281(7) 0.049(4) Uani 1 1 d . . .
C45 C -0.3084(7) 0.5787(9) 0.0733(7) 0.052(4) Uani 1 1 d . . .
H45 H -0.2716 0.5927 0.0497 0.062 Uiso 1 1 calc R . .
C46 C -0.3743(8) 0.6213(10) 0.0560(7) 0.060(4) Uani 1 1 d . . .
H46 H -0.3816 0.6677 0.0221 0.071 Uiso 1 1 calc R . .
C47 C -0.4317(7) 0.5957(11) 0.0891(7) 0.057(4) Uani 1 1 d . . .
H47 H -0.4777 0.6207 0.0745 0.068 Uiso 1 1 calc R . .
C48 C -0.4200(6) 0.5344(10) 0.1425(7) 0.052(4) Uani 1 1 d . . .
H48 H -0.4574 0.5210 0.1657 0.062 Uiso 1 1 calc R . .
C49 C -0.3519(7) 0.4917(9) 0.1626(7) 0.050(4) Uani 1 1 d . . .
C50 C -0.3905(7) 0.4096(12) 0.2515(7) 0.074(5) Uani 1 1 d . . .
H50A H -0.4063 0.4713 0.2682 0.111 Uiso 1 1 calc R . .
H50B H -0.3729 0.3657 0.2872 0.111 Uiso 1 1 calc R . .
H50C H -0.4303 0.3784 0.2238 0.111 Uiso 1 1 calc R . .
C51 C 0.6005(10) 0.1096(17) 0.2373(11) 0.139(9) Uani 1 1 d . . .
H51A H 0.6050 0.0376 0.2423 0.167 Uiso 1 1 calc R . .
H51B H 0.5878 0.1363 0.2775 0.167 Uiso 1 1 calc R . .
Cl1 Cl 0.5310(3) 0.1360(7) 0.1730(4) 0.210(4) Uani 1 1 d . . .
Cl2 Cl 0.6862(3) 0.1605(5) 0.2259(3) 0.138(2) Uani 1 1 d . . .
F1 F 0.9552(4) 0.7351(6) 0.1451(5) 0.088(3) Uani 1 1 d . . .
F2 F 0.9663(5) 0.7452(5) 0.0374(5) 0.102(4) Uani 1 1 d . . .
F3 F 0.9131(4) 0.6101(5) 0.0760(4) 0.078(3) Uani 1 1 d . . .
F4 F 0.8357(3) 0.7137(6) 0.1171(4) 0.063(2) Uani 1 1 d . . .
F5 F 0.8454(5) 0.7226(7) 0.0105(4) 0.098(3) Uani 1 1 d . . .
F6 F 0.8904(4) 0.8469(5) 0.0792(4) 0.058(2) Uani 1 1 d . . .
O1 O 0.2968(4) 0.6941(6) -0.0243(4) 0.049(2) Uani 1 1 d . . .
O2 O -0.3353(4) 0.4289(7) 0.2155(5) 0.056(3) Uani 1 1 d . . .
P1 P 0.90128(18) 0.7277(3) 0.07745(19) 0.0486(9) Uani 1 1 d . . .


_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 C22 1.995(11) . ?
Ir1 C11 2.005(10) . ?
Ir1 N1 2.030(10) . ?
Ir1 N2 2.052(9) . ?
Ir1 N4 2.143(9) . ?
Ir1 N3 2.148(9) . ?
N1 C1 1.368(15) . ?
N1 C5 1.395(14) . ?
N2 C12 1.377(14) . ?
N2 C16 1.391(13) . ?
N3 C23 1.346(13) . ?
N3 C27 1.373(12) . ?
N4 C32 1.355(13) . ?
N4 C28 1.364(14) . ?
C1 C2 1.348(18) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.393(16) . ?
C4 H4 0.9300 . ?
C5 C6 1.452(16) . ?
C6 C7 1.391(15) . ?
C6 C11 1.432(15) . ?
C7 C8 1.367(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.393(16) . ?
C8 H8 0.9300 . ?
C9 C10 1.399(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.422(15) . ?
C10 H10 0.9300 . ?
C12 C13 1.359(15) . ?
C12 H12 0.9300 . ?
C13 C14 1.418(15) . ?
C13 H13 0.9300 . ?
C14 C15 1.376(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.406(15) . ?
C15 H15 0.9300 . ?
C16 C17 1.459(16) . ?
C17 C22 1.379(15) . ?
C17 C18 1.411(14) . ?
C18 C19 1.369(15) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(16) . ?
C19 H19 0.9300 . ?
C20 C21 1.403(15) . ?
C20 H20 0.9300 . ?
C21 C22 1.414(16) . ?
C21 H21 0.9300 . ?
C23 C24 1.354(15) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(15) . ?
C24 H24 0.9300 . ?
C25 C26 1.411(14) . ?
C25 C33 1.448(15) . ?
C26 C27 1.409(14) . ?
C26 H26 0.9300 . ?
C27 C28 1.435(14) . ?
C28 C29 1.379(14) . ?
C29 C30 1.403(15) . ?
C29 H29 0.9300 . ?
C30 C31 1.381(16) . ?
C30 C42 1.501(15) . ?
C31 C32 1.354(15) . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C34 1.333(14) . ?
C33 H33 0.9300 . ?
C34 C35 1.462(15) . ?
C34 H34 0.9300 . ?
C35 C36 1.384(16) . ?
C35 C40 1.386(15) . ?
C36 C37 1.395(15) . ?
C36 H36 0.9300 . ?
C37 C38 1.396(15) . ?
C37 H37 0.9300 . ?
C38 C39 1.361(16) . ?
C38 H38 0.9300 . ?
C39 C40 1.400(16) . ?
C39 H39 0.9300 . ?
C40 O1 1.390(13) . ?
C41 O1 1.427(13) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 C43 1.364(16) . ?
C42 H42 0.9300 . ?
C43 C44 1.464(16) . ?
C43 H43 0.9300 . ?
C44 C49 1.392(16) . ?
C44 C45 1.434(17) . ?
C45 C46 1.354(16) . ?
C45 H45 0.9300 . ?
C46 C47 1.411(17) . ?
C46 H46 0.9300 . ?
C47 C48 1.365(17) . ?
C47 H47 0.9300 . ?
C48 C49 1.400(15) . ?
C48 H48 0.9300 . ?
C49 O2 1.376(14) . ?
C50 O2 1.397(14) . ?
C50 H50A 0.9600 . ?
C50 H50B 0.9600 . ?
C50 H50C 0.9600 . ?
C51 Cl1 1.742(19) . ?
C51 Cl2 1.798(18) . ?
C51 H51A 0.9700 . ?
C51 H51B 0.9700 . ?
F1 P1 1.592(9) . ?
F2 P1 1.601(8) . ?
F3 P1 1.588(7) . ?
F4 P1 1.599(7) . ?
F5 P1 1.598(9) . ?
F6 P1 1.607(7) . ?

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
C22 Ir1 C11 86.5(4) . . ?
C22 Ir1 N1 93.7(4) . . ?
C11 Ir1 N1 81.1(4) . . ?
C22 Ir1 N2 80.4(4) . . ?
C11 Ir1 N2 94.6(4) . . ?
N1 Ir1 N2 172.9(4) . . ?
C22 Ir1 N4 99.8(4) . . ?
C11 Ir1 N4 173.3(4) . . ?
N1 Ir1 N4 96.0(4) . . ?
N2 Ir1 N4 88.9(3) . . ?
C22 Ir1 N3 174.3(4) . . ?
C11 Ir1 N3 97.8(4) . . ?
N1 Ir1 N3 90.8(4) . . ?
N2 Ir1 N3 95.5(4) . . ?
N4 Ir1 N3 76.0(4) . . ?
C1 N1 C5 117.9(11) . . ?
C1 N1 Ir1 126.4(9) . . ?
C5 N1 Ir1 115.7(8) . . ?
C12 N2 C16 121.3(10) . . ?
C12 N2 Ir1 124.8(8) . . ?
C16 N2 Ir1 113.9(8) . . ?
C23 N3 C27 119.6(10) . . ?
C23 N3 Ir1 126.1(8) . . ?
C27 N3 Ir1 114.3(7) . . ?
C32 N4 C28 117.2(10) . . ?
C32 N4 Ir1 125.5(8) . . ?
C28 N4 Ir1 117.2(7) . . ?
C2 C1 N1 124.4(13) . . ?
C2 C1 H1 117.8 . . ?
N1 C1 H1 117.8 . . ?
C1 C2 C3 117.4(15) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 121.4(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 119.6(13) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 N1 119.2(12) . . ?
C4 C5 C6 127.1(12) . . ?
N1 C5 C6 113.8(10) . . ?
C7 C6 C11 120.2(11) . . ?
C7 C6 C5 124.6(12) . . ?
C11 C6 C5 115.1(10) . . ?
C8 C7 C6 120.7(12) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.6(11) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C10 118.8(13) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C10 C11 121.3(12) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C6 117.3(10) . . ?
C10 C11 Ir1 128.4(9) . . ?
C6 C11 Ir1 114.3(8) . . ?
C13 C12 N2 120.9(12) . . ?
C13 C12 H12 119.5 . . ?
N2 C12 H12 119.5 . . ?
C12 C13 C14 120.1(12) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 118.0(11) . . ?
C15 C14 H14 121.0 . . ?
C13 C14 H14 121.0 . . ?
C14 C15 C16 122.4(11) . . ?
C14 C15 H15 118.8 . . ?
C16 C15 H15 118.8 . . ?
N2 C16 C15 116.9(12) . . ?
N2 C16 C17 114.4(10) . . ?
C15 C16 C17 128.7(11) . . ?
C22 C17 C18 124.7(11) . . ?
C22 C17 C16 114.7(10) . . ?
C18 C17 C16 120.5(11) . . ?
C19 C18 C17 117.1(11) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C18 C19 C20 121.9(12) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C19 C20 C21 118.8(13) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C22 122.0(12) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C17 C22 C21 115.3(10) . . ?
C17 C22 Ir1 116.3(9) . . ?
C21 C22 Ir1 128.4(9) . . ?
N3 C23 C24 124.2(11) . . ?
N3 C23 H23 117.9 . . ?
C24 C23 H23 117.9 . . ?
C23 C24 C25 119.6(11) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C24 C25 C26 116.8(11) . . ?
C24 C25 C33 123.8(11) . . ?
C26 C25 C33 119.4(10) . . ?
C27 C26 C25 122.2(11) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
N3 C27 C26 117.5(10) . . ?
N3 C27 C28 118.4(10) . . ?
C26 C27 C28 124.1(10) . . ?
N4 C28 C29 120.6(10) . . ?
N4 C28 C27 114.0(9) . . ?
C29 C28 C27 125.3(11) . . ?
C28 C29 C30 121.9(11) . . ?
C28 C29 H29 119.0 . . ?
C30 C29 H29 119.0 . . ?
C31 C30 C29 115.6(11) . . ?
C31 C30 C42 118.1(11) . . ?
C29 C30 C42 126.3(11) . . ?
C32 C31 C30 121.0(12) . . ?
C32 C31 H31 119.5 . . ?
C30 C31 H31 119.5 . . ?
C31 C32 N4 123.6(12) . . ?
C31 C32 H32 118.2 . . ?
N4 C32 H32 118.2 . . ?
C34 C33 C25 126.6(11) . . ?
C34 C33 H33 116.7 . . ?
C25 C33 H33 116.7 . . ?
C33 C34 C35 129.5(11) . . ?
C33 C34 H34 115.2 . . ?
C35 C34 H34 115.2 . . ?
C36 C35 C40 117.5(11) . . ?
C36 C35 C34 121.8(11) . . ?
C40 C35 C34 120.7(11) . . ?
C35 C36 C37 121.1(11) . . ?
C35 C36 H36 119.4 . . ?
C37 C36 H36 119.4 . . ?
C36 C37 C38 119.2(12) . . ?
C36 C37 H37 120.4 . . ?
C38 C37 H37 120.4 . . ?
C39 C38 C37 121.3(12) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C38 C39 C40 118.1(12) . . ?
C38 C39 H39 121.0 . . ?
C40 C39 H39 121.0 . . ?
C35 C40 O1 115.4(11) . . ?
C35 C40 C39 122.8(12) . . ?
O1 C40 C39 121.7(11) . . ?
O1 C41 H41A 109.5 . . ?
O1 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O1 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C43 C42 C30 123.8(12) . . ?
C43 C42 H42 118.1 . . ?
C30 C42 H42 118.1 . . ?
C42 C43 C44 127.0(12) . . ?
C42 C43 H43 116.5 . . ?
C44 C43 H43 116.5 . . ?
C49 C44 C45 119.0(11) . . ?
C49 C44 C43 126.6(13) . . ?
C45 C44 C43 114.4(12) . . ?
C46 C45 C44 119.9(12) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C45 C46 C47 120.3(13) . . ?
C45 C46 H46 119.8 . . ?
C47 C46 H46 119.8 . . ?
C48 C47 C46 120.4(12) . . ?
C48 C47 H47 119.8 . . ?
C46 C47 H47 119.8 . . ?
C47 C48 C49 120.2(12) . . ?
C47 C48 H48 119.9 . . ?
C49 C48 H48 119.9 . . ?
O2 C49 C44 115.8(11) . . ?
O2 C49 C48 124.2(12) . . ?
C44 C49 C48 120.0(13) . . ?
O2 C50 H50A 109.5 . . ?
O2 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
O2 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
Cl1 C51 Cl2 113.4(10) . . ?
Cl1 C51 H51A 108.9 . . ?
Cl2 C51 H51A 108.9 . . ?
Cl1 C51 H51B 108.9 . . ?
Cl2 C51 H51B 108.9 . . ?
H51A C51 H51B 107.7 . . ?
C40 O1 C41 119.8(9) . . ?
C49 O2 C50 116.6(10) . . ?
F3 P1 F1 90.4(5) . . ?
F3 P1 F5 90.9(5) . . ?
F1 P1 F5 178.2(6) . . ?
F3 P1 F4 90.9(4) . . ?
F1 P1 F4 89.3(4) . . ?
F5 P1 F4 89.5(5) . . ?
F3 P1 F2 90.7(4) . . ?
F1 P1 F2 91.0(5) . . ?
F5 P1 F2 90.2(6) . . ?
F4 P1 F2 178.3(5) . . ?
F3 P1 F6 179.3(5) . . ?
F1 P1 F6 89.1(5) . . ?
F5 P1 F6 89.6(5) . . ?
F4 P1 F6 89.6(4) . . ?
F2 P1 F6 88.7(4) . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.500 0.000 1.000 364.7 160.7
2 1.000 0.500 0.500 364.8 159.7
_platon_squeeze_details          
;
;

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.14
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         1.607
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.171
####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 1019401'
_audit_update_record             
;
2014-08-14 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;
_audit_creation_date             2014-08-14
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C28 H24 N2 O2'
_chemical_formula_sum            'C28 H24 N2 O2'
_chemical_formula_weight         420.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         C26H24N2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.3668(10)
_cell_length_b                   7.3332(7)
_cell_length_c                   12.7466(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.958(11)
_cell_angle_gamma                90.00
_cell_volume                     1056.38(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1462
_cell_measurement_temperature    99.97(13)
_cell_measurement_theta_max      24.9360
_cell_measurement_theta_min      3.2090
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30337
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0577
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3388
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.80
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   66.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -77.0000  -30.0000 120

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   43.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -77.0000   90.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega   42.00   96.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074   38.0000   60.0000 54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0515475000
_diffrn_orient_matrix_UB_12      -0.0551070000
_diffrn_orient_matrix_UB_13      -0.0218309000
_diffrn_orient_matrix_UB_21      0.0341355000
_diffrn_orient_matrix_UB_22      -0.0768689000
_diffrn_orient_matrix_UB_23      0.0284541000
_diffrn_orient_matrix_UB_31      -0.0111417000
_diffrn_orient_matrix_UB_32      0.0197824000
_diffrn_orient_matrix_UB_33      0.0491774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1489
_reflns_number_total             1867
_reflns_odcompleteness_completeness 86.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1867
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.104
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0753P)²+0.1469P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1484
_refine_ls_wR_factor_ref         0.1620
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O1 O 0.83281(13) 0.9516(2) 0.51315(12) 0.0295(4) Uani 1 1 d . . .
N1 N 0.48670(13) 0.0989(2) 0.36562(14) 0.0213(5) Uani 1 1 d . . .
C1 C 0.52036(16) 0.0827(3) 0.47887(17) 0.0197(5) Uani 1 1 d . . .
C2 C 0.59134(16) 0.2124(3) 0.55664(17) 0.0202(5) Uani 1 1 d . . .
H2 H 0.6162 0.1933 0.6351 0.024 Uiso 1 1 calc R . .
C3 C 0.62491(16) 0.3704(3) 0.51680(17) 0.0202(5) Uani 1 1 d . . .
C4 C 0.58761(16) 0.3869(3) 0.39882(17) 0.0229(5) Uani 1 1 d . . .
H4 H 0.6079 0.4892 0.3676 0.027 Uiso 1 1 calc R . .
C5 C 0.52026(17) 0.2502(3) 0.32849(17) 0.0225(5) Uani 1 1 d . . .
H5 H 0.4965 0.2641 0.2497 0.027 Uiso 1 1 calc R . .
C6 C 0.69684(17) 0.5077(3) 0.59963(18) 0.0245(5) Uani 1 1 d . . .
H6 H 0.7251 0.4766 0.6769 0.029 Uiso 1 1 calc R . .
C7 C 0.72548(16) 0.6716(3) 0.57506(17) 0.0229(5) Uani 1 1 d . . .
H7 H 0.7001 0.7017 0.4979 0.028 Uiso 1 1 calc R . .
C8 C 0.79403(16) 0.8100(3) 0.65953(18) 0.0228(5) Uani 1 1 d . . .
C9 C 0.80592(17) 0.8069(3) 0.77291(18) 0.0254(5) Uani 1 1 d . . .
H9 H 0.7674 0.7166 0.7960 0.030 Uiso 1 1 calc R . .
C10 C 0.87338(17) 0.9345(3) 0.85190(18) 0.0269(6) Uani 1 1 d . . .
H10 H 0.8804 0.9304 0.9273 0.032 Uiso 1 1 calc R . .
C11 C 0.93069(18) 1.0691(3) 0.81713(19) 0.0284(6) Uani 1 1 d . . .
H11 H 0.9783 1.1533 0.8705 0.034 Uiso 1 1 calc R . .
C12 C 0.91816(18) 1.0798(3) 0.70538(19) 0.0262(6) Uani 1 1 d . . .
H12 H 0.9556 1.1725 0.6830 0.031 Uiso 1 1 calc R . .
C13 C 0.84928(17) 0.9517(3) 0.62546(18) 0.0232(5) Uani 1 1 d . . .
C14 C 0.86493(19) 1.1125(3) 0.46984(19) 0.0334(6) Uani 1 1 d . . .
H14A H 0.8406 1.1012 0.3884 0.050 Uiso 1 1 calc R . .
H14B H 0.9492 1.1285 0.5061 0.050 Uiso 1 1 calc R . .
H14C H 0.8266 1.2160 0.4859 0.050 Uiso 1 1 calc R . .


_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
O1 C13 1.362(2) . ?
O1 C14 1.426(3) . ?
N1 C1 1.335(2) . ?
N1 C5 1.336(3) . ?
C1 C1 1.495(4) 3_656 ?
C1 C2 1.397(3) . ?
C2 C3 1.394(3) . ?
C3 C4 1.388(3) . ?
C3 C6 1.469(3) . ?
C4 C5 1.377(3) . ?
C6 C7 1.326(3) . ?
C7 C8 1.472(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.406(3) . ?
C9 C10 1.380(3) . ?
C10 C11 1.389(3) . ?
C11 C12 1.371(3) . ?
C12 C13 1.393(3) . ?

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
C13 O1 C14 117.40(17) . . ?
C1 N1 C5 116.84(18) . . ?
N1 C1 C1 117.3(2) . 3_656 ?
N1 C1 C2 122.47(19) . . ?
C2 C1 C1 120.2(2) . 3_656 ?
C3 C2 C1 120.10(18) . . ?
C2 C3 C6 119.39(18) . . ?
C4 C3 C2 116.77(19) . . ?
C4 C3 C6 123.84(19) . . ?
C5 C4 C3 119.26(19) . . ?
N1 C5 C4 124.50(19) . . ?
C7 C6 C3 126.4(2) . . ?
C6 C7 C8 125.6(2) . . ?
C9 C8 C7 122.34(19) . . ?
C9 C8 C13 118.2(2) . . ?
C13 C8 C7 119.44(18) . . ?
C10 C9 C8 121.6(2) . . ?
C9 C10 C11 119.02(19) . . ?
C12 C11 C10 121.0(2) . . ?
C11 C12 C13 119.9(2) . . ?
O1 C13 C8 116.12(19) . . ?
O1 C13 C12 123.72(19) . . ?
C12 C13 C8 120.14(19) . . ?

####################################################################### 
# 
# 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_DARK
_database_code_depnum_ccdc_archive 'CCDC 1050220'
_audit_update_record             
;
2015-02-18 deposited with the CCDC.
2015-11-05 downloaded from the CCDC.
;
_audit_creation_date             2015-02-18
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C50 H40 Ir N4 O2, F6 P'
_chemical_formula_sum            'C50 H40 F6 Ir N4 O2 P'
_chemical_formula_weight         1066.08
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Ir -1.30390 7.98110 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   15.991(12)
_cell_length_b                   13.426(10)
_cell_length_c                   22.927(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.761(12)
_cell_angle_gamma                90
_cell_volume                     4851(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_exptl_absorpt_coefficient_mu    2.850
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_crystal_density_diffrn    1.4597
_exptl_crystal_F_000             2120
_diffrn_reflns_av_R_equivalents  0.1050
_diffrn_reflns_av_unetI/netI     0.1154
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7429
_diffrn_reflns_theta_full        16.840498
_diffrn_reflns_theta_max         16.84
_diffrn_reflns_theta_min         0.90
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.984347
_diffrn_measured_fraction_theta_max 0.984347
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -12
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                1740
_reflns_number_total             2704
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.251274
_refine_diff_density_min         -1.138838
_refine_diff_density_rms         0.204296
_refine_ls_d_res_high            1.226630
_refine_ls_d_res_low             14.095537
_refine_ls_goodness_of_fit_ref   0.971271
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    81
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2704
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.112489
_refine_ls_R_factor_gt           0.070144
_refine_ls_restrained_S_all      1.016437
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)²+23.8897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.189751
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Ir1 Ir 0.72099(8) 0.22360(8) 0.84011(5) 0.0612(6) Uani 1.000000 .
P1 P 0.6332(6) 0.2163(8) 0.4470(4) 0.088(2) Uani 1.000000 .
F1 F 0.7134(15) 0.2083(16) 0.4961(8) 0.157(4) Uani 1.000000 .
F2 F 0.6899(15) 0.1850(16) 0.3985(8) 0.157(4) Uani 1.000000 .
F3 F 0.6520(15) 0.3307(18) 0.4350(8) 0.157(4) Uani 1.000000 .
F4 F 0.5536(15) 0.2226(16) 0.3980(8) 0.157(4) Uani 1.000000 .
F5 F 0.6094(15) 0.1045(18) 0.4592(8) 0.157(4) Uani 1.000000 .
F6 F 0.5819(15) 0.2511(15) 0.4960(8) 0.157(4) Uani 1.000000 .
O1 O 0.5655(12) 0.3049(14) 1.2062(9) 0.095(5) Uani 1.000000 .
O2 O 1.1166(12) 0.7167(14) 0.7815(10) 0.095(5) Uani 1.000000 .
N1 N 0.8053(18) 0.1199(19) 0.8800(9) 0.088(2) Uani 1.000000 .
N2 N 0.6312(16) 0.3179(18) 0.7943(10) 0.088(2) Uani 1.000000 .
N3 N 0.7139(17) 0.2846(19) 0.9257(9) 0.088(2) Uani 1.000000 .
N4 N 0.8072(16) 0.3442(18) 0.8491(10) 0.088(2) Uani 1.000000 .
C1 C 0.644(2) 0.111(2) 0.8432(13) 0.0823(17) Uani 1.000000 .
C2 C 0.555(2) 0.103(2) 0.8213(12) 0.0823(17) Uani 1.000000 .
H2 H 0.528(2) 0.157(2) 0.8004(12) 0.099(2) Uiso 1.000000 R
C3 C 0.507(2) 0.019(2) 0.8301(12) 0.0823(17) Uani 1.000000 .
H3 H 0.449(2) 0.019(2) 0.8172(12) 0.099(2) Uiso 1.000000 R
C4 C 0.547(2) -0.063(2) 0.8580(12) 0.0823(17) Uani 1.000000 .
H4 H 0.516(2) -0.120(2) 0.8603(12) 0.099(2) Uiso 1.000000 R
C5 C 0.629(2) -0.063(2) 0.8816(12) 0.0823(17) Uani 1.000000 .
H5 H 0.654(2) -0.117(2) 0.9030(12) 0.099(2) Uiso 1.000000 R
C6 C 0.680(2) 0.028(2) 0.8726(13) 0.0823(17) Uani 1.000000 .
C7 C 0.766(2) 0.031(2) 0.8957(13) 0.0823(17) Uani 1.000000 .
C8 C 0.826(2) -0.038(2) 0.9263(12) 0.0823(17) Uani 1.000000 .
H8 H 0.805(2) -0.097(2) 0.9388(12) 0.099(2) Uiso 1.000000 R
C9 C 0.911(2) -0.024(2) 0.9387(12) 0.0823(17) Uani 1.000000 .
H9 H 0.946(2) -0.073(2) 0.9583(12) 0.099(2) Uiso 1.000000 R
C10 C 0.947(2) 0.064(2) 0.9222(12) 0.0823(17) Uani 1.000000 .
H10 H 1.005(2) 0.076(2) 0.9303(12) 0.099(2) Uiso 1.000000 R
C11 C 0.890(2) 0.132(2) 0.8927(12) 0.0823(17) Uani 1.000000 .
H11 H 0.912(2) 0.191(2) 0.8807(12) 0.099(2) Uiso 1.000000 R
C12 C 0.7318(13) 0.1851(15) 0.7563(6) 0.0823(17) Uani 1.000000 .
C13 C 0.7889(11) 0.1180(13) 0.7387(8) 0.0823(17) Uani 1.000000 G
H13 H 0.8236(11) 0.0799(13) 0.7668(8) 0.099(2) Uiso 1.000000 R
C14 C 0.7941(10) 0.1079(12) 0.6791(9) 0.0823(17) Uani 1.000000 G
H14 H 0.8323(10) 0.0630(12) 0.6673(9) 0.099(2) Uiso 1.000000 R
C15 C 0.7422(13) 0.1649(14) 0.6370(6) 0.0823(17) Uani 1.000000 G
H15 H 0.7456(13) 0.1581(14) 0.5971(6) 0.099(2) Uiso 1.000000 R
C16 C 0.6851(11) 0.2320(12) 0.6546(8) 0.0823(17) Uani 1.000000 G
H16 H 0.6503(11) 0.2701(12) 0.6265(8) 0.099(2) Uiso 1.000000 R
C17 C 0.6799(11) 0.2421(12) 0.7142(9) 0.0823(17) Uani 1.000000 G
C18 C 0.623(2) 0.311(2) 0.7351(13) 0.0823(17) Uani 1.000000 .
C19 C 0.5607(18) 0.373(2) 0.6990(13) 0.0823(17) Uani 1.000000 .
H19 H 0.5534(18) 0.371(2) 0.6579(13) 0.099(2) Uiso 1.000000 R
C20 C 0.5130(19) 0.434(2) 0.7280(13) 0.0823(17) Uani 1.000000 .
H20 H 0.4728(19) 0.475(2) 0.7059(13) 0.099(2) Uiso 1.000000 R
C21 C 0.5221(19) 0.437(2) 0.7868(13) 0.0823(17) Uani 1.000000 .
H21 H 0.4900(19) 0.481(2) 0.8053(13) 0.099(2) Uiso 1.000000 R
C22 C 0.5785(19) 0.376(2) 0.8191(13) 0.0823(17) Uani 1.000000 .
H22 H 0.5811(19) 0.374(2) 0.8599(13) 0.099(2) Uiso 1.000000 R
C23 C 0.659(2) 0.247(2) 0.9598(13) 0.0823(17) Uani 1.000000 .
H23 H 0.623(2) 0.194(2) 0.9459(13) 0.099(2) Uiso 1.000000 R
C24 C 0.6551(19) 0.289(2) 1.0165(13) 0.0823(17) Uani 1.000000 .
H24 H 0.6171(19) 0.265(2) 1.0396(13) 0.099(2) Uiso 1.000000 R
C25 C 0.710(2) 0.366(2) 1.0359(13) 0.0823(17) Uani 1.000000 .
C26 C 0.765(2) 0.400(2) 0.9998(13) 0.0823(17) Uani 1.000000 .
H26 H 0.802(2) 0.451(2) 1.0135(13) 0.099(2) Uiso 1.000000 R
C27 C 0.767(2) 0.361(2) 0.9449(14) 0.0823(17) Uani 1.000000 .
C28 C 0.820(2) 0.393(2) 0.9040(14) 0.0823(17) Uani 1.000000 .
C29 C 0.880(2) 0.467(2) 0.9162(13) 0.0823(17) Uani 1.000000 .
H29 H 0.889(2) 0.495(2) 0.9539(13) 0.099(2) Uiso 1.000000 R
C30 C 0.926(2) 0.501(2) 0.8755(14) 0.0823(17) Uani 1.000000 .
C31 C 0.9150(19) 0.456(2) 0.8217(13) 0.0823(17) Uani 1.000000 .
H31 H 0.9480(19) 0.474(2) 0.7938(13) 0.099(2) Uiso 1.000000 R
C32 C 0.8507(19) 0.379(2) 0.8082(13) 0.0823(17) Uani 1.000000 .
H32 H 0.8392(19) 0.354(2) 0.7700(13) 0.099(2) Uiso 1.000000 R
C33 C 0.7185(19) 0.416(2) 1.0965(13) 0.0823(17) Uani 1.000000 .
H33 H 0.7565(19) 0.468(2) 1.1073(13) 0.099(2) Uiso 1.000000 R
C34 C 0.6662(19) 0.380(2) 1.1349(10) 0.0823(17) Uani 1.000000 .
H34 H 0.6201(19) 0.341(2) 1.1193(10) 0.099(2) Uiso 1.000000 R
C35 C 0.6808(13) 0.4029(17) 1.2001(10) 0.0823(17) Uani 1.000000 .
C36 C 0.7477(14) 0.4652(16) 1.2231(8) 0.0823(17) Uani 1.000000 .
H36 H 0.7801(14) 0.4971(16) 1.1986(8) 0.099(2) Uiso 1.000000 R
C37 C 0.7645(15) 0.4780(18) 1.2841(7) 0.0823(17) Uani 1.000000 .
H37 H 0.8072(15) 0.5209(18) 1.3016(7) 0.099(2) Uiso 1.000000 R
C38 C 0.7160(12) 0.4253(16) 1.3186(10) 0.0823(17) Uani 1.000000 .
H38 H 0.7291(12) 0.4295(16) 1.3596(10) 0.099(2) Uiso 1.000000 R
C39 C 0.6482(14) 0.3664(16) 1.2928(8) 0.0823(17) Uani 1.000000 .
H39 H 0.6154(14) 0.3351(16) 1.3172(8) 0.099(2) Uiso 1.000000 R
C40 C 0.6275(15) 0.3524(19) 1.2320(7) 0.0823(17) Uani 1.000000 .
C41 C 0.5120(19) 0.2634(19) 1.2443(12) 0.0823(17) Uani 1.000000 .
H41a H 0.457(4) 0.248(12) 1.2216(18) 0.123(3) Uiso 1.000000 G
H41b H 0.537(6) 0.204(7) 1.262(6) 0.123(3) Uiso 1.000000 G
H41c H 0.505(9) 0.311(5) 1.275(5) 0.123(3) Uiso 1.000000 G
C42 C 0.9859(18) 0.584(2) 0.8923(12) 0.0823(17) Uani 1.000000 .
H42 H 0.9926(18) 0.607(2) 0.9311(12) 0.099(2) Uiso 1.000000 R
C43 C 1.0305(17) 0.6295(19) 0.8560(12) 0.0823(17) Uani 1.000000 .
H43 H 1.0296(17) 0.6060(19) 0.8178(12) 0.099(2) Uiso 1.000000 R
C44 C 1.0816(18) 0.718(2) 0.8779(14) 0.0823(17) Uani 1.000000 .
C45 C 1.0892(19) 0.757(2) 0.9302(13) 0.0823(17) Uani 1.000000 .
H45 H 1.0593(19) 0.728(2) 0.9571(13) 0.099(2) Uiso 1.000000 R
C46 C 1.1383(18) 0.840(2) 0.9490(13) 0.0823(17) Uani 1.000000 .
H46 H 1.1375(18) 0.871(2) 0.9854(13) 0.099(2) Uiso 1.000000 R
C47 C 1.1886(19) 0.875(2) 0.9098(13) 0.0823(17) Uani 1.000000 .
H47 H 1.2256(19) 0.927(2) 0.9216(13) 0.099(2) Uiso 1.000000 R
C48 C 1.1866(19) 0.835(2) 0.8536(13) 0.0823(17) Uani 1.000000 .
H48 H 1.2219(19) 0.858(2) 0.8283(13) 0.099(2) Uiso 1.000000 R
C49 C 1.130(2) 0.759(2) 0.8375(14) 0.0823(17) Uani 1.000000 .
C50 C 1.1573(19) 0.7604(19) 0.7394(12) 0.0823(17) Uani 1.000000 .
H50a H 1.158(9) 0.831(2) 0.744(5) 0.123(3) Uiso 1.000000 G
H50b H 1.214(4) 0.736(10) 0.744(5) 0.123(3) Uiso 1.000000 G
H50c H 1.128(6) 0.744(10) 0.7006(12) 0.123(3) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ir1 N1 2.04(2) .
Ir1 N2 2.06(2) .
Ir1 N3 2.15(2) .
Ir1 N4 2.11(3) .
Ir1 C1 1.96(3) .
Ir1 C12 2.026(14) .
P1 F1 1.56(2) .
P1 F2 1.61(2) .
P1 F3 1.60(2) .
P1 F4 1.55(2) .
P1 F5 1.58(2) .
P1 F6 1.57(2) .
O1 C40 1.24(2) .
O1 C41 1.43(3) .
O2 C49 1.39(3) .
O2 C50 1.38(3) .
N1 C7 1.43(3) .
N1 C11 1.34(3) .
N2 C18 1.34(3) .
N2 C22 1.34(3) .
N3 C23 1.37(3) .
N3 C27 1.35(3) .
N4 C28 1.41(3) .
N4 C32 1.34(3) .
C1 C2 1.43(3) .
C1 C6 1.37(3) .
C2 H2 0.9300 .
C2 C3 1.40(3) .
C3 H3 0.9300 .
C3 C4 1.38(3) .
C4 H4 0.9300 .
C4 C5 1.33(3) .
C5 H5 0.9300 .
C5 C6 1.50(4) .
C6 C7 1.38(4) .
C7 C8 1.43(3) .
C8 H8 0.9300 .
C8 C9 1.36(3) .
C9 H9 0.9300 .
C9 C10 1.39(3) .
C10 H10 0.9300 .
C10 C11 1.39(3) .
C11 H11 0.9300 .
C12 C13 1.3900 .
C12 C17 1.3900 .
C13 H13 0.9300 .
C13 C14 1.3900 .
C14 H14 0.9300 .
C14 C15 1.3900 .
C15 H15 0.9300 .
C15 C16 1.3900 .
C16 H16 0.9300 .
C16 C17 1.3900 .
C17 C18 1.44(3) .
C18 C19 1.44(3) .
C19 H19 0.9300 .
C19 C20 1.37(3) .
C20 H20 0.9300 .
C20 C21 1.33(3) .
C21 H21 0.9300 .
C21 C22 1.35(3) .
C22 H22 0.9300 .
C23 H23 0.9300 .
C23 C24 1.43(3) .
C24 H24 0.9300 .
C24 C25 1.38(3) .
C25 C26 1.38(4) .
C25 C33 1.53(4) .
C26 H26 0.9300 .
C26 C27 1.37(4) .
C27 C28 1.43(4) .
C28 C29 1.37(3) .
C29 H29 0.9300 .
C29 C30 1.37(4) .
C30 C31 1.36(3) .
C30 C42 1.48(3) .
C31 H31 0.9300 .
C31 C32 1.45(3) .
C32 H32 0.9300 .
C33 H33 0.9300 .
C33 C34 1.40(3) .
C34 H34 0.9300 .
C34 C35 1.504(17) .
C35 C36 1.39(3) .
C35 C40 1.39(3) .
C36 H36 0.9300 .
C36 C37 1.39(2) .
C37 H37 0.9300 .
C37 C38 1.39(3) .
C38 H38 0.9300 .
C38 C39 1.39(3) .
C39 H39 0.9300 .
C39 C40 1.39(2) .
C41 H41a 0.9600 .
C41 H41b 0.9600 .
C41 H41c 0.9600 .
C42 H42 0.9300 .
C42 C43 1.329(17) .
C43 H43 0.9300 .
C43 C44 1.476(17) .
C44 C45 1.30(3) .
C44 C49 1.42(4) .
C45 H45 0.9300 .
C45 C46 1.39(3) .
C46 H46 0.9300 .
C46 C47 1.38(4) .
C47 H47 0.9300 .
C47 C48 1.39(3) .
C48 H48 0.9300 .
C48 C49 1.37(3) .
C50 H50a 0.9600 .
C50 H50b 0.9600 .
C50 H50c 0.9600 .

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
N2 Ir1 N1 174.6(9) . .
N3 Ir1 N1 89.1(9) . .
N3 Ir1 N2 95.3(9) . .
N4 Ir1 N1 96.2(10) . .
N4 Ir1 N2 88.0(9) . .
N4 Ir1 N3 75.7(10) . .
C1 Ir1 N1 80.1(12) . .
C1 Ir1 N2 96.1(11) . .
C1 Ir1 N3 97.6(11) . .
C1 Ir1 N4 172.5(10) . .
C12 Ir1 N1 95.5(9) . .
C12 Ir1 N2 80.6(9) . .
C12 Ir1 N3 172.1(9) . .
C12 Ir1 N4 97.4(9) . .
C12 Ir1 C1 89.5(10) . .
F2 P1 F1 89.4(12) . .
F3 P1 F1 92.0(12) . .
F3 P1 F2 89.2(12) . .
F4 P1 F1 179.1(14) . .
F4 P1 F2 90.1(11) . .
F4 P1 F3 88.7(12) . .
F5 P1 F1 90.0(12) . .
F5 P1 F2 93.2(12) . .
F5 P1 F3 176.9(14) . .
F5 P1 F4 89.3(13) . .
F6 P1 F1 88.3(11) . .
F6 P1 F2 176.7(14) . .
F6 P1 F3 88.5(12) . .
F6 P1 F4 92.2(12) . .
F6 P1 F5 89.2(12) . .
C41 O1 C40 115(2) . .
C50 O2 C49 117(2) . .
C7 N1 Ir1 113(2) . .
C11 N1 Ir1 125(2) . .
C11 N1 C7 121(3) . .
C18 N2 Ir1 115(2) . .
C22 N2 Ir1 125(2) . .
C22 N2 C18 120(3) . .
C23 N3 Ir1 121(2) . .
C27 N3 Ir1 117(2) . .
C27 N3 C23 121(3) . .
C28 N4 Ir1 116(2) . .
C32 N4 Ir1 127(2) . .
C32 N4 C28 117(3) . .
C2 C1 Ir1 129(2) . .
C6 C1 Ir1 115(2) . .
C6 C1 C2 115(3) . .
H2 C2 C1 118.6(18) . .
C3 C2 C1 123(3) . .
C3 C2 H2 118.6(19) . .
H3 C3 C2 120.3(19) . .
C4 C3 C2 119(3) . .
C4 C3 H3 120.3(19) . .
H4 C4 C3 118.6(18) . .
C5 C4 C3 123(3) . .
C5 C4 H4 119(2) . .
H5 C5 C4 121(2) . .
C6 C5 C4 118(3) . .
C6 C5 H5 121.2(18) . .
C5 C6 C1 122(3) . .
C7 C6 C1 118(3) . .
C7 C6 C5 119(3) . .
C6 C7 N1 112(3) . .
C8 C7 N1 112(3) . .
C8 C7 C6 136(3) . .
H8 C8 C7 117.1(19) . .
C9 C8 C7 126(3) . .
C9 C8 H8 117.1(19) . .
H9 C9 C8 119.8(19) . .
C10 C9 C8 120(3) . .
C10 C9 H9 120(2) . .
H10 C10 C9 122(2) . .
C11 C10 C9 115(3) . .
C11 C10 H10 122.4(19) . .
C10 C11 N1 125(3) . .
H11 C11 N1 117.3(17) . .
H11 C11 C10 117.3(19) . .
C13 C12 Ir1 127.3(12) . .
C17 C12 Ir1 112.4(12) . .
C17 C12 C13 120.00000000(2) . .
H13 C13 C12 120.0(7) . .
C14 C13 C12 120.0 . .
C14 C13 H13 120.0(7) . .
H14 C14 C13 120.0(7) . .
C15 C14 C13 120.0 . .
C15 C14 H14 120.0(7) . .
H15 C15 C14 120.0(7) . .
C16 C15 C14 120.0 . .
C16 C15 H15 120.0(7) . .
H16 C16 C15 120.0(7) . .
C17 C16 C15 120.0 . .
C17 C16 H16 120.0(7) . .
C16 C17 C12 120.0 . .
C18 C17 C12 117.5(19) . .
C18 C17 C16 122.5(19) . .
C17 C18 N2 115(3) . .
C19 C18 N2 119(3) . .
C19 C18 C17 126(3) . .
H19 C19 C18 121.6(18) . .
C20 C19 C18 117(3) . .
C20 C19 H19 121.6(19) . .
H20 C20 C19 118.8(19) . .
C21 C20 C19 122(3) . .
C21 C20 H20 119(2) . .
H21 C21 C20 120(2) . .
C22 C21 C20 119(3) . .
C22 C21 H21 120.5(19) . .
C21 C22 N2 122(3) . .
H22 C22 N2 118.9(17) . .
H22 C22 C21 119(2) . .
H23 C23 N3 119.9(17) . .
C24 C23 N3 120(3) . .
C24 C23 H23 119.9(19) . .
H24 C24 C23 121.0(19) . .
C25 C24 C23 118(3) . .
C25 C24 H24 121(2) . .
C26 C25 C24 119(3) . .
C33 C25 C24 125(3) . .
C33 C25 C26 116(3) . .
H26 C26 C25 118.6(19) . .
C27 C26 C25 123(3) . .
C27 C26 H26 119(2) . .
C26 C27 N3 118(3) . .
C28 C27 N3 115(3) . .
C28 C27 C26 127(3) . .
C27 C28 N4 116(3) . .
C29 C28 N4 121(3) . .
C29 C28 C27 124(3) . .
H29 C29 C28 118(2) . .
C30 C29 C28 123(3) . .
C30 C29 H29 118.5(19) . .
C31 C30 C29 118(3) . .
C42 C30 C29 119(3) . .
C42 C30 C31 124(3) . .
H31 C31 C30 120(2) . .
C32 C31 C30 119(3) . .
C32 C31 H31 120.4(18) . .
C31 C32 N4 122(3) . .
H32 C32 N4 118.9(17) . .
H32 C32 C31 118.9(18) . .
H33 C33 C25 121.7(18) . .
C34 C33 C25 117(3) . .
C34 C33 H33 121.7(16) . .
H34 C34 C33 118.4(16) . .
C35 C34 C33 123(3) . .
C35 C34 H34 118.4(14) . .
C36 C35 C34 119(2) . .
C40 C35 C34 114.8(19) . .
C40 C35 C36 127(2) . .
H36 C36 C35 121.3(12) . .
C37 C36 C35 117(2) . .
C37 C36 H36 121.3(13) . .
H37 C37 C36 120.7(13) . .
C38 C37 C36 119(2) . .
C38 C37 H37 120.7(13) . .
H38 C38 C37 119.4(13) . .
C39 C38 C37 121(2) . .
C39 C38 H38 119.4(13) . .
H39 C39 C38 118.7(13) . .
C40 C39 C38 123(2) . .
C40 C39 H39 118.7(13) . .
C35 C40 O1 120.8(18) . .
C39 C40 O1 126(2) . .
C39 C40 C35 113(2) . .
H41a C41 O1 109.5 . .
H41b C41 O1 109.5 . .
H41b C41 H41a 109.5 . .
H41c C41 O1 109.5 . .
H41c C41 H41a 109.5 . .
H41c C41 H41b 109.5 . .
H42 C42 C30 117.5(17) . .
C43 C42 C30 125(3) . .
C43 C42 H42 117.5(18) . .
H43 C43 C42 120.7(18) . .
C44 C43 C42 119(3) . .
C44 C43 H43 120.7(17) . .
C45 C44 C43 127(3) . .
C49 C44 C43 115(3) . .
C49 C44 C45 118(3) . .
H45 C45 C44 117(2) . .
C46 C45 C44 125(3) . .
C46 C45 H45 117.4(19) . .
H46 C46 C45 122.4(19) . .
C47 C46 C45 115(3) . .
C47 C46 H46 122.4(18) . .
H47 C47 C46 118.3(18) . .
C48 C47 C46 123(3) . .
C48 C47 H47 118(2) . .
H48 C48 C47 122(2) . .
C49 C48 C47 116(3) . .
C49 C48 H48 122(2) . .
C44 C49 O2 115(3) . .
C48 C49 O2 123(3) . .
C48 C49 C44 122(3) . .
H50a C50 O2 109.5 . .
H50b C50 O2 109.5 . .
H50b C50 H50a 109.5 . .
H50c C50 O2 109.5 . .
H50c C50 H50a 109.5 . .
H50c C50 H50b 109.5 . .

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.311 0.500 417.3 103.5 ?
2 0.500 -0.553 0.000 417.3 103.5 ?

loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C35 C34 1 1.5000 0.0200 -0.0043
C35 C40 1 1.3900 0.0010 -0.0000
C36 C35 1 1.3900 0.0010 -0.0000
C37 C36 1 1.3900 0.0010 -0.0001
C38 C37 1 1.3900 0.0010 -0.0000
C39 C38 1 1.3900 0.0010 -0.0000
C40 C39 1 1.3900 0.0010 -0.0001
C42 C43 1 1.3500 0.0200 0.0213
C44 C43 1 1.4700 0.0200 -0.0064

