# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shelx_x
_database_code_depnum_ccdc_archive 'CCDC 1048465'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;

_audit_creation_date             2015-02-09T14:55:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_common            phen(N-Mes)2
_chemical_formula_moiety         'C30 H28 N4'
_chemical_formula_sum            'C30 H28 N4'
_chemical_formula_weight         444.56

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4981(5)
_cell_length_b                   10.2782(5)
_cell_length_c                   13.8108(8)
_cell_angle_alpha                92.571(4)
_cell_angle_beta                 109.723(5)
_cell_angle_gamma                107.893(5)
_cell_volume                     1191.05(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_theta_min      3.4489
_cell_measurement_theta_max      73.6627

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

_exptl_crystal_size_max          0.1946
_exptl_crystal_size_mid          0.1303
_exptl_crystal_size_min          0.0707
_exptl_crystal_density_diffrn    1.24
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 9 0.039
-1 6 -3 0.0443
6 -3 -1 0.088
2 -6 3 0.0696
-6 0 3 0.0846
0 3 -8 0.0364
-1 -4 7 0.0509
1 -1 -9 0.0264
3 2 -8 0.0624
-4 5 -2 0.0698
0 4 5 0.0464
0 -5 -5 0.0708
-2 -2 -5 0.0689
4 -6 -3 0.0732

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.94537
_exptl_absorpt_correction_T_max  1
_exptl_crystal_description       prism
_exptl_crystal_colour            red

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

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3385
_diffrn_orient_matrix_ub_11      -0.0934523644
_diffrn_orient_matrix_ub_12      -0.1030804935
_diffrn_orient_matrix_ub_13      -0.1031687887
_diffrn_orient_matrix_ub_21      -0.1118073729
_diffrn_orient_matrix_ub_22      -0.0878340766
_diffrn_orient_matrix_ub_23      0.0497186491
_diffrn_orient_matrix_ub_31      -0.1112473403
_diffrn_orient_matrix_ub_32      0.0847286286
_diffrn_orient_matrix_ub_33      -0.0364849344
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_number            10930
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         7.637
_diffrn_reflns_theta_max         73.506
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_number_total             4642
_reflns_number_gt                3843
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0541P)²+0.2349P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4642
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.1073
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.18
_refine_diff_density_rms         0.036

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.58807(12) 0.32017(11) 0.09515(8) 0.0281(2) Uani 1 d . .
N4 N 0.81016(12) 0.17797(11) 0.20863(8) 0.0267(2) Uani 1 d . .
C12 C 0.80137(16) 0.27783(13) -0.06991(10) 0.0284(3) Uani 1 d . .
N2 N 1.08894(14) 0.36192(12) -0.01516(9) 0.0338(3) Uani 1 d . .
C7 C 0.68902(14) 0.28381(12) 0.06944(9) 0.0249(3) Uani 1 d . .
C14 C 0.59962(14) 0.33941(13) 0.20077(9) 0.0253(3) Uani 1 d . .
C1 C 0.96238(15) 0.31847(12) 0.01309(10) 0.0273(3) Uani 1 d . .
C8 C 0.66984(15) 0.26659(13) -0.04210(9) 0.0273(3) Uani 1 d . .
C19 C 0.60044(16) 0.37997(15) 0.40228(10) 0.0330(3) Uani 1 d . .
C26 C 1.08535(16) -0.01859(14) 0.30608(11) 0.0327(3) Uani 1 d . .
H15 H 1.1142 -0.0881 0.2812 0.039 Uiso 1 calc . .
N1 N 0.78948(15) 0.25993(12) -0.16978(9) 0.0362(3) Uani 1 d . .
C21 C 0.93216(14) 0.13300(13) 0.27444(10) 0.0256(3) Uani 1 d . .
C22 C 0.97519(15) 0.02908(13) 0.23539(10) 0.0294(3) Uani 1 d . .
C16 C 0.50211(15) 0.23388(13) 0.23406(10) 0.0294(3) Uani 1 d . .
C4 C 1.12895(15) 0.36059(13) 0.19473(11) 0.0303(3) Uani 1 d . .
H3 H 1.1424 0.3604 0.2646 0.036 Uiso 1 calc . .
C24 C 1.10515(16) 0.13511(14) 0.44813(10) 0.0318(3) Uani 1 d . .
H18 H 1.1484 0.1705 0.519 0.038 Uiso 1 calc . .
C5 C 0.97716(15) 0.31212(12) 0.11745(10) 0.0259(3) Uani 1 d . .
C15 C 0.69075(15) 0.46788(13) 0.26475(10) 0.0287(3) Uani 1 d . .
C20 C 0.68701(16) 0.48534(14) 0.36438(10) 0.0314(3) Uani 1 d . .
H28 H 0.7449 0.5712 0.4071 0.038 Uiso 1 calc . .
C6 C 0.83069(14) 0.25425(12) 0.14073(9) 0.0245(3) Uani 1 d . .
C23 C 0.99459(15) 0.18476(13) 0.38152(10) 0.0284(3) Uani 1 d . .
C3 C 1.25892(16) 0.40895(14) 0.16595(12) 0.0342(3) Uani 1 d . .
H2 H 1.3616 0.4437 0.216 0.041 Uiso 1 calc . .
C9 C 0.52180(17) 0.23938(15) -0.12051(10) 0.0348(3) Uani 1 d . .
H8 H 0.4329 0.2334 -0.1042 0.042 Uiso 1 calc . .
C18 C 0.50647(16) 0.25562(14) 0.33489(11) 0.0335(3) Uani 1 d . .
H27 H 0.4446 0.1848 0.3582 0.04 Uiso 1 calc . .
C2 C 1.23299(17) 0.40456(14) 0.06095(12) 0.0365(3) Uani 1 d . .
H1 H 1.3215 0.4331 0.042 0.044 Uiso 1 calc . .
C29 C 1.27620(19) -0.01558(17) 0.48618(13) 0.0443(4) Uani 1 d . .
H19A H 1.2653 -0.1062 0.4567 0.066 Uiso 1 calc . .
H19B H 1.2608 -0.0197 0.5513 0.066 Uiso 1 calc . .
H19C H 1.3808 0.0476 0.4977 0.066 Uiso 1 calc . .
C25 C 1.15307(16) 0.03395(14) 0.41191(11) 0.0322(3) Uani 1 d . .
C28 C 0.94325(17) 0.29443(15) 0.42071(11) 0.0366(3) Uani 1 d . .
H21A H 0.973 0.3019 0.495 0.055 Uiso 1 calc . .
H21B H 0.8298 0.2696 0.3882 0.055 Uiso 1 calc . .
H21C H 0.9942 0.3818 0.404 0.055 Uiso 1 calc . .
C27 C 0.90708(19) -0.03005(15) 0.12132(11) 0.0402(3) Uani 1 d . .
H20A H 0.965 0.0299 0.0859 0.06 Uiso 1 calc . .
H20B H 0.7971 -0.0377 0.0925 0.06 Uiso 1 calc . .
H20C H 0.9155 -0.1202 0.1125 0.06 Uiso 1 calc . .
C10 C 0.5094(2) 0.22147(17) -0.22303(11) 0.0438(4) Uani 1 d . .
H9 H 0.4121 0.2032 -0.2774 0.053 Uiso 1 calc . .
C30 C 0.6154(2) 0.39703(19) 0.51501(11) 0.0490(4) Uani 1 d . .
H30A H 0.5157 0.3453 0.52 0.074 Uiso 1 calc . .
H30B H 0.6432 0.4933 0.541 0.074 Uiso 1 calc . .
H30C H 0.6967 0.3633 0.5557 0.074 Uiso 1 calc . .
C11 C 0.6454(2) 0.23138(17) -0.24287(11) 0.0433(4) Uani 1 d . .
H10 H 0.6355 0.2171 -0.3122 0.052 Uiso 1 calc . .
C13 C 0.79078(19) 0.58345(16) 0.22753(13) 0.0431(4) Uani 1 d . .
H24A H 0.8305 0.6676 0.2764 0.065 Uiso 1 calc . .
H24B H 0.727 0.5961 0.1605 0.065 Uiso 1 calc . .
H24C H 0.8786 0.5603 0.222 0.065 Uiso 1 calc . .
C17 C 0.39577(19) 0.10120(15) 0.16059(13) 0.0448(4) Uani 1 d . .
H26A H 0.3299 0.0437 0.1927 0.067 Uiso 1 calc . .
H26B H 0.4596 0.0535 0.1444 0.067 Uiso 1 calc . .
H26C H 0.3297 0.1214 0.0976 0.067 Uiso 1 calc . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C7 1.2740(16) . ?
N3 C14 1.4254(15) . ?
N4 C6 1.2758(16) . ?
N4 C21 1.4278(15) . ?
C12 N1 1.3448(16) . ?
C12 C8 1.4002(18) . ?
C12 C1 1.4861(18) . ?
N2 C2 1.3374(19) . ?
N2 C1 1.3412(16) . ?
C7 C8 1.4846(17) . ?
C7 C6 1.5020(16) . ?
C14 C15 1.3965(18) . ?
C14 C16 1.4001(17) . ?
C1 C5 1.4067(17) . ?
C8 C9 1.3898(18) . ?
C19 C20 1.3846(19) . ?
C19 C18 1.388(2) . ?
C19 C30 1.5120(18) . ?
C26 C25 1.387(2) . ?
C26 C22 1.3988(18) . ?
N1 C11 1.331(2) . ?
C21 C22 1.4015(17) . ?
C21 C23 1.4019(18) . ?
C22 C27 1.5014(19) . ?
C16 C18 1.3851(19) . ?
C16 C17 1.4991(19) . ?
C4 C3 1.3787(18) . ?
C4 C5 1.3922(18) . ?
C24 C23 1.3888(18) . ?
C24 C25 1.3915(18) . ?
C5 C6 1.4843(17) . ?
C15 C20 1.3933(18) . ?
C15 C13 1.5062(19) . ?
C23 C28 1.5042(17) . ?
C3 C2 1.383(2) . ?
C9 C10 1.3795(19) . ?
C29 C25 1.5107(18) . ?
C10 C11 1.384(2) . ?

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
C7 N3 C14 122.05(10) . . ?
C6 N4 C21 122.73(10) . . ?
N1 C12 C8 122.54(12) . . ?
N1 C12 C1 118.02(12) . . ?
C8 C12 C1 119.36(11) . . ?
C2 N2 C1 117.24(12) . . ?
N3 C7 C8 119.02(11) . . ?
N3 C7 C6 127.03(11) . . ?
C8 C7 C6 113.94(10) . . ?
C15 C14 C16 120.96(11) . . ?
C15 C14 N3 119.99(11) . . ?
C16 C14 N3 118.52(11) . . ?
N2 C1 C5 122.51(12) . . ?
N2 C1 C12 117.95(11) . . ?
C5 C1 C12 119.53(11) . . ?
C9 C8 C12 118.91(12) . . ?
C9 C8 C7 120.79(12) . . ?
C12 C8 C7 120.30(11) . . ?
C20 C19 C18 117.75(12) . . ?
C20 C19 C30 121.00(13) . . ?
C18 C19 C30 121.15(13) . . ?
C25 C26 C22 122.39(12) . . ?
C11 N1 C12 116.96(12) . . ?
C22 C21 C23 120.87(11) . . ?
C22 C21 N4 121.09(11) . . ?
C23 C21 N4 117.65(11) . . ?
C26 C22 C21 117.99(12) . . ?
C26 C22 C27 120.24(12) . . ?
C21 C22 C27 121.77(12) . . ?
C18 C16 C14 118.62(12) . . ?
C18 C16 C17 121.62(12) . . ?
C14 C16 C17 119.76(12) . . ?
C3 C4 C5 118.91(13) . . ?
C23 C24 C25 121.95(12) . . ?
C4 C5 C1 118.50(11) . . ?
C4 C5 C6 122.71(11) . . ?
C1 C5 C6 118.79(11) . . ?
C20 C15 C14 117.84(12) . . ?
C20 C15 C13 121.09(12) . . ?
C14 C15 C13 121.07(12) . . ?
C19 C20 C15 122.59(12) . . ?
N4 C6 C5 128.01(11) . . ?
N4 C6 C7 117.72(11) . . ?
C5 C6 C7 114.14(10) . . ?
C24 C23 C21 118.76(12) . . ?
C24 C23 C28 121.90(12) . . ?
C21 C23 C28 119.32(11) . . ?
C4 C3 C2 118.42(13) . . ?
C10 C9 C8 118.65(13) . . ?
C16 C18 C19 122.01(12) . . ?
N2 C2 C3 124.27(12) . . ?
C26 C25 C24 117.99(12) . . ?
C26 C25 C29 121.42(13) . . ?
C24 C25 C29 120.59(13) . . ?
C9 C10 C11 118.26(14) . . ?
N1 C11 C10 124.65(13) . . ?

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

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

data_shelx_x
_database_code_depnum_ccdc_archive 'CCDC 1048466'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;

_audit_creation_date             2015-02-09T14:46:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_common            phen(N-o-Xyl)2
_chemical_formula_moiety         'C28 H24 N4'
_chemical_formula_sum            'C28 H24 N4'
_chemical_formula_weight         416.51

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14
_chemical_absolute_configuration ?
_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                   15.6277(2)
_cell_length_b                   7.31640(10)
_cell_length_c                   20.3483(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.6660(10)
_cell_angle_gamma                90
_cell_volume                     2269.98(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.00(14)
_cell_measurement_reflns_used    6281
_cell_measurement_theta_min      2.8958
_cell_measurement_theta_max      73.4827

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

_exptl_crystal_size_max          0.2071
_exptl_crystal_size_mid          0.1818
_exptl_crystal_size_min          0.1202
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 0 13 0.0754
5 0 -13 0.0754
-4 -4 4 0.091
-1 5 1 0.0836
-1 0 -13 0.0691
10 0 0 0.0779
3 0 11 0.0475
-5 -3 -7 0.0814
1 -4 6 0.0931
-7 1 -6 0.066
-9 -2 4 0.0751
7 3 2 0.0772
0 -5 -3 0.1051
-5 3 -6 0.0777
-8 -1 -6 0.0636
-10 -1 4 0.0728

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_T_max  0.949
_exptl_crystal_description       fragment
_exptl_crystal_colour            red

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

_diffrn_ambient_temperature      180.00(14)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3385
_diffrn_orient_matrix_ub_11      -0.0020517
_diffrn_orient_matrix_ub_12      0.2104821
_diffrn_orient_matrix_ub_13      0.0019088
_diffrn_orient_matrix_ub_21      0.0975615
_diffrn_orient_matrix_ub_22      0.0024581
_diffrn_orient_matrix_ub_23      0.0360254
_diffrn_orient_matrix_ub_31      0.0261506
_diffrn_orient_matrix_ub_32      0.0073047
_diffrn_orient_matrix_ub_33      -0.0686783
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_number            10877
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.459
_diffrn_reflns_theta_max         26.251
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.968
_reflns_number_total             4445
_reflns_number_gt                3905
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
        (compiled Jan 23 2012,18:06:46)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0493P)²+0.6181P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4445
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.036

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
N3 N 0.12267(6) 0.02964(15) 0.32107(5) 0.0286(2) Uani 1 d . .
N1 N 0.40545(7) 0.10416(16) 0.27363(5) 0.0325(2) Uani 1 d . .
C14 C 0.05980(7) -0.05895(17) 0.35113(6) 0.0269(3) Uani 1 d . .
N4 N 0.22714(6) -0.07673(14) 0.45465(5) 0.0263(2) Uani 1 d . .
N2 N 0.43992(7) -0.24297(16) 0.32497(6) 0.0329(2) Uani 1 d . .
C6 C 0.25180(7) -0.10240(16) 0.39970(6) 0.0249(2) Uani 1 d . .
C16 C 0.01778(8) 0.04389(18) 0.39262(6) 0.0312(3) Uani 1 d . .
C21 C 0.27396(8) -0.14816(17) 0.51722(6) 0.0265(3) Uani 1 d . .
C1 C 0.37272(7) -0.15047(17) 0.34026(6) 0.0271(3) Uani 1 d . .
C7 C 0.20493(7) 0.00621(17) 0.34006(6) 0.0255(2) Uani 1 d . .
C8 C 0.26412(8) 0.09833(17) 0.30285(6) 0.0267(3) Uani 1 d . .
C12 C 0.34759(8) 0.02522(18) 0.30478(6) 0.0271(3) Uani 1 d . .
C10 C 0.29843(9) 0.3375(2) 0.23342(7) 0.0369(3) Uani 1 d . .
H10 H 0.2837 0.4432 0.2081 0.044 Uiso 1 calc . .
C18 C -0.05344(9) -0.0328(2) 0.41275(7) 0.0374(3) Uani 1 d . .
H18 H -0.082 0.0334 0.4406 0.045 Uiso 1 calc . .
C5 C 0.32625(8) -0.21415(17) 0.38763(6) 0.0268(3) Uani 1 d . .
C2 C 0.46175(9) -0.4020(2) 0.35588(7) 0.0373(3) Uani 1 d . .
H2 H 0.5077 -0.4675 0.345 0.045 Uiso 1 calc . .
C22 C 0.35095(8) -0.06093(19) 0.55064(6) 0.0330(3) Uani 1 d . .
C15 C 0.03254(8) -0.23612(19) 0.33077(6) 0.0319(3) Uani 1 d . .
C23 C 0.23666(9) -0.29161(18) 0.54665(6) 0.0331(3) Uani 1 d . .
C4 C 0.35150(9) -0.38020(19) 0.41943(7) 0.0338(3) Uani 1 d . .
H4 H 0.3225 -0.4261 0.4512 0.041 Uiso 1 calc . .
C3 C 0.42016(9) -0.4759(2) 0.40326(7) 0.0386(3) Uani 1 d . .
H3 H 0.4381 -0.5874 0.4237 0.046 Uiso 1 calc . .
C20 C -0.03953(9) -0.3069(2) 0.35191(7) 0.0386(3) Uani 1 d . .
H20 H -0.059 -0.4242 0.3388 0.046 Uiso 1 calc . .
C19 C -0.08272(9) -0.2062(2) 0.39200(7) 0.0405(3) Uani 1 d . .
H19 H -0.1314 -0.2549 0.405 0.049 Uiso 1 calc . .
C9 C 0.23919(8) 0.25597(18) 0.26539(6) 0.0321(3) Uani 1 d . .
H9 H 0.1836 0.3055 0.262 0.038 Uiso 1 calc . .
C11 C 0.38080(9) 0.2582(2) 0.23997(7) 0.0361(3) Uani 1 d . .
H11 H 0.4211 0.3164 0.2196 0.043 Uiso 1 calc . .
C26 C 0.39149(9) -0.1243(2) 0.61435(7) 0.0399(3) Uani 1 d . .
H26 H 0.4431 -0.0691 0.6373 0.048 Uiso 1 calc . .
C24 C 0.27982(11) -0.3496(2) 0.61055(7) 0.0422(3) Uani 1 d . .
H24 H 0.2566 -0.4455 0.631 0.051 Uiso 1 calc . .
C25 C 0.35683(10) -0.2668(2) 0.64411(7) 0.0436(4) Uani 1 d . .
H25 H 0.385 -0.3075 0.6867 0.052 Uiso 1 calc . .
C13 C 0.07946(10) -0.3452(2) 0.28696(8) 0.0449(4) Uani 1 d . .
H13A H 0.0488 -0.458 0.2745 0.067 Uiso 1 calc . .
H13B H 0.1381 -0.3708 0.3113 0.067 Uiso 1 calc . .
H13C H 0.0814 -0.2765 0.2471 0.067 Uiso 1 calc . .
C28 C 0.15409(10) -0.3809(2) 0.50801(8) 0.0455(4) Uani 1 d . .
H28A H 0.1679 -0.4588 0.4738 0.068 Uiso 1 calc . .
H28B H 0.1134 -0.2885 0.4873 0.068 Uiso 1 calc . .
H28C H 0.1284 -0.4523 0.5382 0.068 Uiso 1 calc . .
C17 C 0.05178(10) 0.2305(2) 0.41520(8) 0.0428(3) Uani 1 d . .
H17A H 0.013 0.2876 0.4396 0.064 Uiso 1 calc . .
H17B H 0.0549 0.3034 0.3766 0.064 Uiso 1 calc . .
H17C H 0.1092 0.2198 0.4439 0.064 Uiso 1 calc . .
C27 C 0.38731(11) 0.0999(2) 0.51946(8) 0.0495(4) Uani 1 d . .
H27A H 0.437 0.1486 0.5509 0.074 Uiso 1 calc . .
H27B H 0.343 0.1924 0.5081 0.074 Uiso 1 calc . .
H27C H 0.4052 0.0611 0.4794 0.074 Uiso 1 calc . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C7 1.2702(15) . ?
N3 C14 1.4225(15) . ?
N1 C11 1.3313(18) . ?
N1 C12 1.3432(16) . ?
C14 C16 1.3974(18) . ?
C14 C15 1.3986(18) . ?
N4 C6 1.2740(16) . ?
N4 C21 1.4216(15) . ?
N2 C2 1.3309(18) . ?
N2 C1 1.3421(16) . ?
C6 C5 1.4858(16) . ?
C6 C7 1.5003(16) . ?
C16 C18 1.3861(18) . ?
C16 C17 1.4999(19) . ?
C21 C23 1.3975(18) . ?
C21 C22 1.3996(18) . ?
C1 C5 1.4074(17) . ?
C1 C12 1.4843(18) . ?
C7 C8 1.4799(16) . ?
C8 C9 1.3902(18) . ?
C8 C12 1.4024(17) . ?
C10 C9 1.3786(18) . ?
C10 C11 1.391(2) . ?
C18 C19 1.383(2) . ?
C5 C4 1.3922(18) . ?
C2 C3 1.385(2) . ?
C22 C26 1.3915(18) . ?
C22 C27 1.506(2) . ?
C15 C20 1.3907(19) . ?
C15 C13 1.5019(19) . ?
C23 C24 1.3932(19) . ?
C23 C28 1.505(2) . ?
C4 C3 1.3802(19) . ?
C20 C19 1.380(2) . ?
C26 C25 1.375(2) . ?
C24 C25 1.386(2) . ?

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
C7 N3 C14 123.79(10) . . ?
C11 N1 C12 117.26(11) . . ?
C16 C14 C15 121.67(11) . . ?
C16 C14 N3 118.35(11) . . ?
C15 C14 N3 119.29(11) . . ?
C6 N4 C21 122.44(10) . . ?
C2 N2 C1 117.63(11) . . ?
N4 C6 C5 128.66(11) . . ?
N4 C6 C7 116.35(11) . . ?
C5 C6 C7 114.77(10) . . ?
C18 C16 C14 118.34(12) . . ?
C18 C16 C17 122.09(12) . . ?
C14 C16 C17 119.56(11) . . ?
C23 C21 C22 121.95(11) . . ?
C23 C21 N4 118.60(11) . . ?
C22 C21 N4 119.11(11) . . ?
N2 C1 C5 122.64(12) . . ?
N2 C1 C12 117.45(11) . . ?
C5 C1 C12 119.91(11) . . ?
N3 C7 C8 119.17(11) . . ?
N3 C7 C6 126.84(11) . . ?
C8 C7 C6 113.95(10) . . ?
C9 C8 C12 118.61(11) . . ?
C9 C8 C7 121.80(11) . . ?
C12 C8 C7 119.59(11) . . ?
N1 C12 C8 122.75(12) . . ?
N1 C12 C1 117.92(11) . . ?
C8 C12 C1 119.29(11) . . ?
C9 C10 C11 118.50(13) . . ?
C19 C18 C16 120.96(13) . . ?
C4 C5 C1 118.10(11) . . ?
C4 C5 C6 123.77(11) . . ?
C1 C5 C6 118.12(11) . . ?
N2 C2 C3 124.02(12) . . ?
C26 C22 C21 117.91(13) . . ?
C26 C22 C27 121.06(13) . . ?
C21 C22 C27 121.00(12) . . ?
C20 C15 C14 117.92(12) . . ?
C20 C15 C13 121.31(13) . . ?
C14 C15 C13 120.77(12) . . ?
C24 C23 C21 117.81(13) . . ?
C24 C23 C28 122.65(13) . . ?
C21 C23 C28 119.51(12) . . ?
C3 C4 C5 119.20(12) . . ?
C4 C3 C2 118.40(13) . . ?
C19 C20 C15 121.21(13) . . ?
C20 C19 C18 119.87(13) . . ?
C10 C9 C8 118.78(12) . . ?
N1 C11 C10 124.03(12) . . ?
C25 C26 C22 121.33(13) . . ?
C25 C24 C23 121.14(14) . . ?
C26 C25 C24 119.84(13) . . ?

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

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

data_shelx_x
_database_code_depnum_ccdc_archive 'CCDC 1048467'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;

_audit_creation_date             2015-02-09T14:17:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_common            '{(ppy)2 Ir [phen(N-o-Xyl)2]} (PF6) . MeCN'
_chemical_formula_moiety         'C50 H40 Ir N6, F6 P, C2 H3 N'
_chemical_formula_sum            'C52 H43 F6 Ir N7 P'
_chemical_formula_weight         1103.1

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9794(4)
_cell_length_b                   16.0111(6)
_cell_length_c                   17.5265(8)
_cell_angle_alpha                113.881(4)
_cell_angle_beta                 92.391(4)
_cell_angle_gamma                101.791(3)
_cell_volume                     2233.54(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150.1(4)
_cell_measurement_reflns_used    8597
_cell_measurement_theta_min      4.961
_cell_measurement_theta_max      76.219

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

_exptl_crystal_size_max          0.104
_exptl_crystal_size_mid          0.0633
_exptl_crystal_size_min          0.041
_exptl_crystal_density_diffrn    1.64
_exptl_crystal_F_000             1100
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 9 1 0.0135
0 -9 0 0.0301
2 -8 -4 0.0197
-4 3 7 0.0591
5 1 -7 0.014
-4 8 -6 0.0315
-2 -1 -9 0.0187
3 -3 9 0.0342
4 -8 6 0.0228

_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    6.732
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.818
_exptl_crystal_description       coloumn
_exptl_crystal_colour            brown

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

_diffrn_ambient_temperature      150.1(4)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  mirror
_diffrn_detector_area_resol_mean 10.3385
_diffrn_orient_matrix_ub_11      0.1113351
_diffrn_orient_matrix_ub_12      -0.0030765
_diffrn_orient_matrix_ub_13      0.0675798
_diffrn_orient_matrix_ub_21      0.1373898
_diffrn_orient_matrix_ub_22      0.041575
_diffrn_orient_matrix_ub_23      -0.0341955
_diffrn_orient_matrix_ub_31      -0.0072031
_diffrn_orient_matrix_ub_32      0.1001229
_diffrn_orient_matrix_ub_33      0.0607162
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0865
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_number            19581
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         7.456
_diffrn_reflns_theta_max         74.484
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_number_total             9011
_reflns_number_gt                7805
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'

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

_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0605P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9011
_refine_ls_number_parameters     605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1344
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_restrained_S_all      1.155
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.069
_refine_diff_density_min         -2.258
_refine_diff_density_rms         0.179

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

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.771 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8381(7) 0.7924(4) 0.6533(4) 0.0248(12) Uani 1 d . .
C2 C 1.0267(8) 0.8748(4) 0.8071(4) 0.0266(12) Uani 1 d . .
C3 C 0.8375(7) 0.9522(4) 0.5684(4) 0.0226(11) Uani 1 d . .
H3 H 0.7917 0.8881 0.5455 0.027 Uiso 1 calc . .
C4 C 0.8086(7) 1.0037(4) 0.5246(4) 0.0239(11) Uani 1 d . .
H4 H 0.7434 0.9749 0.4737 0.029 Uiso 1 calc . .
C5 C 0.8790(7) 1.0991(4) 0.5584(4) 0.0231(11) Uani 1 d . .
H5 H 0.8617 1.1349 0.5298 0.028 Uiso 1 calc . .
C6 C 0.9761(7) 1.1414(4) 0.6353(4) 0.0211(11) Uani 1 d . .
C7 C 0.9952(7) 1.0859(4) 0.6765(3) 0.0197(11) Uani 1 d . .
C8 C 1.0960(7) 1.1242(4) 0.7561(4) 0.0191(10) Uani 1 d . .
C9 C 1.2203(7) 1.0939(4) 0.8572(4) 0.0222(11) Uani 1 d . .
H9 H 1.2359 1.0515 0.8788 0.027 Uiso 1 calc . .
C10 C 1.2986(8) 1.1878(5) 0.9002(4) 0.0265(12) Uani 1 d . .
H10 H 1.3702 1.2072 0.9476 0.032 Uiso 1 calc . .
C11 C 1.2682(7) 1.2521(4) 0.8714(4) 0.0255(12) Uani 1 d . .
H11 H 1.3188 1.3154 0.8996 0.031 Uiso 1 calc . .
C12 C 1.1614(7) 1.2215(4) 0.7998(4) 0.0226(11) Uani 1 d . .
C13 C 1.1073(7) 1.2850(4) 0.7677(4) 0.0240(12) Uani 1 d . .
C14 C 1.0473(7) 1.2439(4) 0.6757(4) 0.0233(11) Uani 1 d . .
C15 C 0.6843(8) 0.7608(5) 0.6547(4) 0.0304(13) Uani 1 d . .
H15 H 0.6301 0.8025 0.6881 0.036 Uiso 1 calc . .
C16 C 0.6089(9) 0.6668(6) 0.6066(5) 0.0396(17) Uani 1 d . .
H16 H 0.5042 0.6468 0.6067 0.048 Uiso 1 calc . .
C17 C 0.6879(9) 0.6032(5) 0.5590(5) 0.0383(16) Uani 1 d . .
H17 H 0.6382 0.5399 0.5299 0.046 Uiso 1 calc . .
C18 C 0.8422(9) 0.6339(5) 0.5544(5) 0.0338(14) Uani 1 d . .
H18 H 0.8952 0.5917 0.5206 0.041 Uiso 1 calc . .
C19 C 0.9175(8) 0.7288(5) 0.6011(4) 0.0286(13) Uani 1 d . .
C20 C 1.0754(7) 0.7675(4) 0.5959(4) 0.0222(11) Uani 1 d . .
C21 C 1.1757(8) 0.7178(4) 0.5461(4) 0.0286(13) Uani 1 d . .
H21 H 1.1427 0.6531 0.5139 0.034 Uiso 1 calc . .
C22 C 1.3206(8) 0.7642(5) 0.5450(4) 0.0289(13) Uani 1 d . .
H22 H 1.3857 0.7317 0.5113 0.035 Uiso 1 calc . .
C23 C 1.2703(7) 0.9070(4) 0.6434(4) 0.0250(12) Uani 1 d . .
H23 H 1.3028 0.9715 0.6764 0.03 Uiso 1 calc . .
C24 C 0.7203(8) 1.0154(5) 0.7910(5) 0.0328(14) Uani 1 d . .
H24 H 0.7193 1.0291 0.7443 0.039 Uiso 1 calc . .
C25 C 0.6174(11) 1.0444(7) 0.8473(6) 0.052(2) Uani 1 d . .
H25 H 0.5495 1.0778 0.8393 0.062 Uiso 1 calc . .
C26 C 0.6185(14) 1.0221(9) 0.9161(8) 0.071(4) Uani 1 d . .
H26 H 0.552 1.0414 0.9555 0.085 Uiso 1 calc . .
C27 C 0.7183(12) 0.9717(8) 0.9255(7) 0.058(3) Uani 1 d . .
H27 H 0.7176 0.9551 0.9706 0.07 Uiso 1 calc . .
C28 C 0.8211(8) 0.9450(5) 0.8676(5) 0.0329(14) Uani 1 d . .
C29 C 0.9368(9) 0.8947(5) 0.8727(4) 0.0318(14) Uani 1 d . .
C30 C 0.9589(11) 0.8667(7) 0.9367(6) 0.047(2) Uani 1 d . .
H30 H 0.8986 0.8808 0.98 0.057 Uiso 1 calc . .
C31 C 1.1412(9) 0.8268(5) 0.8091(4) 0.0323(14) Uani 1 d . .
H31 H 1.204 0.8138 0.7669 0.039 Uiso 1 calc . .
C32 C 1.1610(11) 0.7988(6) 0.8732(5) 0.0428(18) Uani 1 d . .
H32 H 1.2364 0.7668 0.8737 0.051 Uiso 1 calc . .
C33 C 1.3706(8) 0.8617(5) 0.5952(4) 0.0301(13) Uani 1 d . .
H33 H 1.4691 0.8946 0.5957 0.036 Uiso 1 calc . .
C34 C 1.1096(9) 1.3864(5) 0.6561(4) 0.0301(13) Uani 1 d . .
C35 C 1.0101(9) 1.4467(5) 0.6776(4) 0.0342(15) Uani 1 d . .
C36 C 1.0700(11) 1.5413(5) 0.6937(5) 0.0417(18) Uani 1 d . .
H36 H 1.0065 1.583 0.7088 0.05 Uiso 1 calc . .
C37 C 1.2216(11) 1.5734(5) 0.6873(5) 0.0429(18) Uani 1 d . .
H37 H 1.2596 1.6361 0.6978 0.052 Uiso 1 calc . .
C38 C 1.3161(10) 1.5127(5) 0.6654(5) 0.0391(16) Uani 1 d . .
H38 H 1.4184 1.5354 0.662 0.047 Uiso 1 calc . .
C39 C 1.2634(9) 1.4179(5) 0.6480(4) 0.0328(14) Uani 1 d . .
C40 C 1.3653(10) 1.3513(6) 0.6205(6) 0.0466(19) Uani 1 d . .
H40A H 1.3088 1.2895 0.6112 0.07 Uiso 1 calc . .
H40B H 1.4516 1.372 0.6635 0.07 Uiso 1 calc . .
H40C H 1.401 1.3497 0.5692 0.07 Uiso 1 calc . .
C41 C 0.8472(10) 1.4106(6) 0.6844(6) 0.0453(18) Uani 1 d . .
H41A H 0.7955 1.4608 0.6998 0.068 Uiso 1 calc . .
H41B H 0.8435 1.3867 0.7266 0.068 Uiso 1 calc . .
H41C H 0.7975 1.361 0.6311 0.068 Uiso 1 calc . .
C42 C 0.8983(10) 1.3022(5) 0.9156(5) 0.0362(15) Uani 1 d . .
H42A H 0.8862 1.2789 0.8554 0.054 Uiso 1 calc . .
H42B H 0.8111 1.3258 0.9363 0.054 Uiso 1 calc . .
H42C H 0.9059 1.2521 0.9312 0.054 Uiso 1 calc . .
C43 C 1.0417(9) 1.3801(5) 0.9531(4) 0.0314(14) Uani 1 d . .
C44 C 1.1358(9) 1.4105(4) 0.9025(4) 0.0291(13) Uani 1 d . .
C45 C 1.2644(9) 1.4865(5) 0.9376(5) 0.0341(14) Uani 1 d . .
C46 C 1.3581(11) 1.5185(6) 0.8805(6) 0.050(2) Uani 1 d . .
H46A H 1.3115 1.4813 0.823 0.075 Uiso 1 calc . .
H46B H 1.4605 1.5108 0.887 0.075 Uiso 1 calc . .
H46C H 1.3619 1.5836 0.8952 0.075 Uiso 1 calc . .
C47 C 1.3054(10) 1.5285(5) 1.0244(5) 0.0394(17) Uani 1 d . .
H47 H 1.3932 1.5773 1.0485 0.047 Uiso 1 calc . .
C48 C 1.2173(11) 1.4986(6) 1.0757(4) 0.0423(18) Uani 1 d . .
H48 H 1.2463 1.527 1.1338 0.051 Uiso 1 calc . .
C49 C 1.0860(10) 1.4264(5) 1.0403(4) 0.0374(16) Uani 1 d . .
H49 H 1.0257 1.4081 1.0754 0.045 Uiso 1 calc . .
N1 N 1.1264(6) 0.8622(3) 0.6451(3) 0.0183(9) Uani 1 d . .
N2 N 1.1235(6) 1.0620(3) 0.7862(3) 0.0193(9) Uani 1 d . .
N3 N 0.9292(6) 0.9914(3) 0.6430(3) 0.0187(9) Uani 1 d . .
N4 N 0.8204(6) 0.9686(4) 0.8014(3) 0.0248(10) Uani 1 d . .
N5 N 1.0483(7) 1.2885(4) 0.6292(3) 0.0278(11) Uani 1 d . .
N6 N 1.0948(7) 1.3676(4) 0.8130(3) 0.0293(12) Uani 1 d . .
N7 N 0.5428(13) 0.7558(8) 0.8935(7) 0.077(3) Uani 1 d . .
F1 F 0.4766(9) 0.1387(5) 0.7542(5) 0.074(2) Uani 1 d . .
F2 F 0.3586(5) 0.1615(3) 0.6534(3) 0.0478(11) Uani 1 d . .
F3 F 0.5400(6) 0.2806(3) 0.7499(3) 0.0494(12) Uani 1 d . .
F4 F 0.5872(7) 0.2071(4) 0.6158(3) 0.0523(12) Uani 1 d . .
F5 F 0.7086(6) 0.1873(5) 0.7203(4) 0.0613(15) Uani 1 d . .
F6 F 0.5274(7) 0.0686(4) 0.6227(4) 0.0632(16) Uani 1 d . .
P1 P 0.5356(2) 0.17569(12) 0.68666(11) 0.0292(3) Uani 1 d . .
Ir1 Ir 0.97707(3) 0.92283(2) 0.72102(2) 0.01914(10) Uani 1 d . .
C50 C 0.6185(13) 0.7092(8) 0.8535(7) 0.059(2) Uani 1 d . .
C51 C 0.7115(15) 0.6495(9) 0.8048(7) 0.068(3) Uani 1 d . .
H51A H 0.7985 0.6538 0.8411 0.102 Uiso 1 calc . .
H51B H 0.7465 0.6693 0.7624 0.102 Uiso 1 calc . .
H51C H 0.6517 0.5856 0.7784 0.102 Uiso 1 calc . .
C52 C 1.0683(12) 0.8184(7) 0.9368(6) 0.051(2) Uani 1 d . .
H52 H 1.0806 0.7988 0.9794 0.062 Uiso 1 calc . .



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

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C15 1.375(9) . ?
C1 C19 1.407(10) . ?
C1 Ir1 2.033(6) . ?
C2 C29 1.401(9) . ?
C2 C31 1.411(9) . ?
C2 Ir1 2.022(6) . ?
C3 N3 1.348(8) . ?
C3 C4 1.386(9) . ?
C4 C5 1.388(9) . ?
C5 C6 1.399(8) . ?
C6 C7 1.384(8) . ?
C6 C14 1.482(8) . ?
C7 N3 1.368(8) . ?
C7 C8 1.455(8) . ?
C8 N2 1.359(7) . ?
C8 C12 1.407(8) . ?
C9 N2 1.334(8) . ?
C9 C10 1.390(9) . ?
C10 C11 1.383(9) . ?
C11 C12 1.395(9) . ?
C12 C13 1.492(8) . ?
C13 N6 1.270(9) . ?
C13 C14 1.499(8) . ?
C14 N5 1.281(8) . ?
C15 C16 1.394(11) . ?
C16 C17 1.375(12) . ?
C17 C18 1.389(11) . ?
C18 C19 1.401(10) . ?
C19 C20 1.449(9) . ?
C20 N1 1.370(8) . ?
C20 C21 1.415(9) . ?
C21 C22 1.366(10) . ?
C22 C33 1.408(10) . ?
C23 N1 1.352(8) . ?
C23 C33 1.373(9) . ?
C24 N4 1.333(8) . ?
C24 C25 1.387(11) . ?
C25 C26 1.389(13) . ?
C26 C27 1.369(13) . ?
C27 C28 1.398(11) . ?
C28 N4 1.358(9) . ?
C28 C29 1.459(10) . ?
C29 C30 1.387(10) . ?
C30 C52 1.368(12) . ?
C31 C32 1.384(10) . ?
C32 C52 1.392(13) . ?
C34 C35 1.399(11) . ?
C34 C39 1.404(11) . ?
C34 N5 1.417(8) . ?
C35 C36 1.405(10) . ?
C35 C41 1.487(11) . ?
C36 C37 1.380(13) . ?
C37 C38 1.369(12) . ?
C38 C39 1.393(10) . ?
C39 C40 1.491(11) . ?
C42 C43 1.502(11) . ?
C43 C49 1.399(10) . ?
C43 C44 1.408(10) . ?
C44 C45 1.398(11) . ?
C44 N6 1.429(8) . ?
C45 C47 1.389(10) . ?
C45 C46 1.510(11) . ?
C47 C48 1.384(13) . ?
C48 C49 1.383(13) . ?
N1 Ir1 2.036(5) . ?
N2 Ir1 2.148(5) . ?
N3 Ir1 2.148(4) . ?
N4 Ir1 2.062(5) . ?
N7 C50 1.154(16) . ?
F1 P1 1.590(5) . ?
F2 P1 1.608(5) . ?
F3 P1 1.585(4) . ?
F4 P1 1.572(5) . ?
F5 P1 1.584(5) . ?
F6 P1 1.608(5) . ?
C50 C51 1.438(17) . ?

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
C15 C1 C19 119.0(6) . . ?
C15 C1 Ir1 128.6(5) . . ?
C19 C1 Ir1 112.5(5) . . ?
C29 C2 C31 117.8(6) . . ?
C29 C2 Ir1 114.3(5) . . ?
C31 C2 Ir1 127.8(5) . . ?
N3 C3 C4 122.7(5) . . ?
C3 C4 C5 118.5(6) . . ?
C4 C5 C6 120.1(5) . . ?
C7 C6 C5 117.9(5) . . ?
C7 C6 C14 120.1(5) . . ?
C5 C6 C14 121.8(5) . . ?
N3 C7 C6 122.6(5) . . ?
N3 C7 C8 116.0(5) . . ?
C6 C7 C8 121.3(5) . . ?
N2 C8 C12 121.8(5) . . ?
N2 C8 C7 117.0(5) . . ?
C12 C8 C7 121.2(5) . . ?
N2 C9 C10 122.6(5) . . ?
C11 C10 C9 118.9(6) . . ?
C10 C11 C12 119.7(6) . . ?
C11 C12 C8 117.9(6) . . ?
C11 C12 C13 124.6(6) . . ?
C8 C12 C13 117.5(5) . . ?
N6 C13 C12 125.3(6) . . ?
N6 C13 C14 117.3(6) . . ?
C12 C13 C14 117.0(5) . . ?
N5 C14 C6 117.0(5) . . ?
N5 C14 C13 126.8(6) . . ?
C6 C14 C13 116.2(5) . . ?
C1 C15 C16 120.6(7) . . ?
C17 C16 C15 120.7(7) . . ?
C16 C17 C18 119.9(7) . . ?
C17 C18 C19 119.6(7) . . ?
C18 C19 C1 120.2(7) . . ?
C18 C19 C20 123.0(7) . . ?
C1 C19 C20 116.7(6) . . ?
N1 C20 C21 119.5(6) . . ?
N1 C20 C19 113.9(6) . . ?
C21 C20 C19 126.7(6) . . ?
C22 C21 C20 120.4(6) . . ?
C21 C22 C33 119.4(6) . . ?
N1 C23 C33 122.9(6) . . ?
N4 C24 C25 122.4(7) . . ?
C24 C25 C26 118.2(7) . . ?
C27 C26 C25 119.5(8) . . ?
C26 C27 C28 120.2(8) . . ?
N4 C28 C27 119.6(7) . . ?
N4 C28 C29 115.1(6) . . ?
C27 C28 C29 125.3(7) . . ?
C30 C29 C2 120.8(7) . . ?
C30 C29 C28 123.9(7) . . ?
C2 C29 C28 115.3(6) . . ?
C52 C30 C29 120.7(8) . . ?
C32 C31 C2 120.7(7) . . ?
C31 C32 C52 120.1(7) . . ?
C23 C33 C22 118.4(6) . . ?
C35 C34 C39 121.6(6) . . ?
C35 C34 N5 119.0(7) . . ?
C39 C34 N5 118.6(7) . . ?
C34 C35 C36 117.9(7) . . ?
C34 C35 C41 120.2(7) . . ?
C36 C35 C41 121.9(8) . . ?
C37 C36 C35 120.9(7) . . ?
C38 C37 C36 119.9(7) . . ?
C37 C38 C39 121.9(8) . . ?
C38 C39 C34 117.6(7) . . ?
C38 C39 C40 121.6(8) . . ?
C34 C39 C40 120.8(7) . . ?
C49 C43 C44 117.3(7) . . ?
C49 C43 C42 121.0(7) . . ?
C44 C43 C42 121.7(6) . . ?
C45 C44 C43 121.7(6) . . ?
C45 C44 N6 118.1(6) . . ?
C43 C44 N6 120.0(7) . . ?
C47 C45 C44 118.6(7) . . ?
C47 C45 C46 121.8(8) . . ?
C44 C45 C46 119.6(7) . . ?
C48 C47 C45 120.9(8) . . ?
C49 C48 C47 119.8(6) . . ?
C48 C49 C43 121.6(7) . . ?
C23 N1 C20 119.4(5) . . ?
C23 N1 Ir1 125.1(4) . . ?
C20 N1 Ir1 115.4(4) . . ?
C9 N2 C8 118.9(5) . . ?
C9 N2 Ir1 126.3(4) . . ?
C8 N2 Ir1 114.2(4) . . ?
C3 N3 C7 118.2(5) . . ?
C3 N3 Ir1 127.1(4) . . ?
C7 N3 Ir1 114.7(4) . . ?
C24 N4 C28 120.1(6) . . ?
C24 N4 Ir1 125.0(5) . . ?
C28 N4 Ir1 114.9(4) . . ?
C14 N5 C34 125.5(6) . . ?
C13 N6 C44 122.0(5) . . ?
F4 P1 F5 91.3(3) . . ?
F4 P1 F3 91.8(3) . . ?
F5 P1 F3 91.5(3) . . ?
F4 P1 F1 176.6(4) . . ?
F5 P1 F1 90.9(4) . . ?
F3 P1 F1 90.7(4) . . ?
F4 P1 F6 88.9(3) . . ?
F5 P1 F6 89.5(3) . . ?
F3 P1 F6 178.8(3) . . ?
F1 P1 F6 88.5(4) . . ?
F4 P1 F2 90.2(3) . . ?
F5 P1 F2 178.4(3) . . ?
F3 P1 F2 89.3(3) . . ?
F1 P1 F2 87.7(3) . . ?
F6 P1 F2 89.6(3) . . ?
C2 Ir1 C1 86.4(3) . . ?
C2 Ir1 N1 93.4(2) . . ?
C1 Ir1 N1 80.8(2) . . ?
C2 Ir1 N4 80.3(2) . . ?
C1 Ir1 N4 94.3(2) . . ?
N1 Ir1 N4 172.28(19) . . ?
C2 Ir1 N3 172.6(2) . . ?
C1 Ir1 N3 100.0(2) . . ?
N1 Ir1 N3 91.37(18) . . ?
N4 Ir1 N3 95.34(19) . . ?
C2 Ir1 N2 96.8(2) . . ?
C1 Ir1 N2 176.7(2) . . ?
N1 Ir1 N2 98.05(19) . . ?
N4 Ir1 N2 87.2(2) . . ?
N3 Ir1 N2 76.95(19) . . ?
N7 C50 C51 178.4(12) . . ?
C30 C52 C32 120.0(7) . . ?

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

# END of CIF
