# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc1mg8jw
_database_code_depnum_ccdc_archive 'CCDC 1503268'
_audit_update_record             
;
2016-09-24 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;
_audit_creation_date             2016-09-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C37 H25 N5'
_chemical_formula_sum            'C37 H25 N5'
_chemical_formula_weight         539.62
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.981(2)
_cell_length_b                   9.6424(17)
_cell_length_c                   20.807(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.981(4)
_cell_angle_gamma                90
_cell_volume                     2804.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21682
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.232
_exptl_crystal_size_min          0.216
_exptl_transmission_factor_max   0.984
_exptl_transmission_factor_min   0.979
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            21045
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_min         3.213
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4317
_reflns_number_total             6369
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0966P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1625
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C9(H9), C8(H8), C3(H3), C15(H15), C21(H21), C25(H25),
 C1(H1), C22(H22), C24(H24), C28(H28), C27(H27), C33(H33), C31(H31), C30(H30),
 C16(H16), C18(H18), C29(H29), C35(H35), C19(H19), C34(H34), C37(H37), C17(H17),
  C36(H36)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.55942(10) 0.21920(15) 0.05141(7) 0.0344(3) Uani 1 1 d . . . . .
N4 N 0.19637(10) -0.01669(15) 0.05925(7) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.41082(11) 0.37033(15) 0.00238(7) 0.0363(4) Uani 1 1 d . . . . .
N3 N 0.31666(10) -0.14483(14) 0.10173(7) 0.0293(3) Uani 1 1 d . . . . .
C7 C 0.45539(12) 0.02556(17) 0.07981(8) 0.0285(4) Uani 1 1 d . . . . .
C6 C 0.35768(12) -0.02305(17) 0.07891(8) 0.0282(4) Uani 1 1 d . . . . .
C12 C 0.47071(12) 0.16103(17) 0.05383(8) 0.0297(4) Uani 1 1 d . . . . .
C5 C 0.28213(12) 0.05299(17) 0.05337(8) 0.0295(4) Uani 1 1 d . . . . .
C11 C 0.39055(12) 0.24318(16) 0.02718(8) 0.0296(4) Uani 1 1 d . . . . .
C4 C 0.29607(12) 0.18902(17) 0.02704(8) 0.0299(4) Uani 1 1 d . . . . .
C10 C 0.63357(13) 0.14480(19) 0.07320(9) 0.0365(4) Uani 1 1 d . . . . .
H10 H 0.6942 0.1841 0.0714 0.044 Uiso 1 1 calc R . . . .
C13 C 0.21898(12) -0.13422(17) 0.08922(8) 0.0311(4) Uani 1 1 d . . . . .
C20 C 0.14524(12) -0.23461(18) 0.10949(9) 0.0332(4) Uani 1 1 d . . . . .
C2 C 0.24246(15) 0.4008(2) -0.02196(9) 0.0415(5) Uani 1 1 d . . . . .
H2 H 0.1944 0.4579 -0.0384 0.050 Uiso 1 1 calc R . . . .
C9 C 0.62546(12) 0.01095(19) 0.09867(9) 0.0349(4) Uani 1 1 d . . . . .
H9 H 0.6795 -0.0371 0.1128 0.042 Uiso 1 1 calc R . . . .
C8 C 0.53625(12) -0.04828(17) 0.10243(8) 0.0316(4) Uani 1 1 d . . . . .
H8 H 0.5293 -0.1365 0.1198 0.038 Uiso 1 1 calc R . . . .
C3 C 0.22098(13) 0.27166(19) 0.00210(9) 0.0362(4) Uani 1 1 d . . . . .
H3 H 0.1582 0.2396 0.0019 0.043 Uiso 1 1 calc R . . . .
N5 N -0.08058(11) -0.49459(16) 0.17159(9) 0.0436(4) Uani 1 1 d . . . . .
C15 C 0.41350(12) -0.35741(17) 0.10811(9) 0.0339(4) Uani 1 1 d . . . . .
H15 H 0.4202 -0.3558 0.0637 0.041 Uiso 1 1 calc R . . . .
C21 C 0.15943(13) -0.37749(19) 0.11751(11) 0.0410(5) Uani 1 1 d . . . . .
H21 H 0.2191 -0.4156 0.1094 0.049 Uiso 1 1 calc R . . . .
C14 C 0.36350(11) -0.25323(17) 0.13884(8) 0.0299(4) Uani 1 1 d . . . . .
C25 C 0.05371(12) -0.18183(18) 0.12162(9) 0.0361(4) Uani 1 1 d . . . . .
H25 H 0.0424 -0.0874 0.1165 0.043 Uiso 1 1 calc R . . . .
C1 C 0.33811(15) 0.44467(19) -0.02117(9) 0.0412(5) Uani 1 1 d . . . . .
H1 H 0.3516 0.5315 -0.0382 0.049 Uiso 1 1 calc R . . . .
C22 C 0.08588(13) -0.46269(19) 0.13724(11) 0.0439(5) Uani 1 1 d . . . . .
H22 H 0.0972 -0.5571 0.1425 0.053 Uiso 1 1 calc R . . . .
C26 C -0.09175(12) -0.63577(18) 0.15209(10) 0.0352(4) Uani 1 1 d . . . . .
C24 C -0.02035(13) -0.26705(19) 0.14109(10) 0.0392(4) Uani 1 1 d . . . . .
H24 H -0.0804 -0.2294 0.1486 0.047 Uiso 1 1 calc R . . . .
C32 C -0.14955(13) -0.43403(18) 0.21387(9) 0.0363(4) Uani 1 1 d . . . . .
C28 C -0.08109(13) -0.8154(2) 0.07112(11) 0.0453(5) Uani 1 1 d . . . . .
H28 H -0.0637 -0.8432 0.0301 0.054 Uiso 1 1 calc R . . . .
C27 C -0.06688(13) -0.67870(19) 0.09019(10) 0.0402(4) Uani 1 1 d . . . . .
H27 H -0.0407 -0.6153 0.0617 0.048 Uiso 1 1 calc R . . . .
C33 C -0.11929(15) -0.3804(2) 0.27298(10) 0.0438(5) Uani 1 1 d . . . . .
H33 H -0.0553 -0.3869 0.2855 0.053 Uiso 1 1 calc R . . . .
C31 C -0.13018(13) -0.7329(2) 0.19419(10) 0.0400(4) Uani 1 1 d . . . . .
H31 H -0.1458 -0.7067 0.2357 0.048 Uiso 1 1 calc R . . . .
C30 C -0.14509(13) -0.8691(2) 0.17413(11) 0.0452(5) Uani 1 1 d . . . . .
H30 H -0.1716 -0.9329 0.2022 0.054 Uiso 1 1 calc R . . . .
C16 C 0.45363(13) -0.4647(2) 0.14455(11) 0.0440(5) Uani 1 1 d . . . . .
H16 H 0.4873 -0.5353 0.1246 0.053 Uiso 1 1 calc R . . . .
C23 C -0.00520(13) -0.40945(18) 0.14948(10) 0.0376(4) Uani 1 1 d . . . . .
C18 C 0.39569(17) -0.3584(3) 0.24124(11) 0.0567(6) Uani 1 1 d . . . . .
H18 H 0.3910 -0.3585 0.2858 0.068 Uiso 1 1 calc R . . . .
C29 C -0.12094(13) -0.9107(2) 0.11272(11) 0.0462(5) Uani 1 1 d . . . . .
H29 H -0.1314 -1.0017 0.0996 0.055 Uiso 1 1 calc R . . . .
C35 C -0.27852(18) -0.3050(2) 0.29516(12) 0.0561(6) Uani 1 1 d . . . . .
H35 H -0.3214 -0.2611 0.3221 0.067 Uiso 1 1 calc R . . . .
C19 C 0.35522(14) -0.2510(2) 0.20564(9) 0.0425(5) Uani 1 1 d . . . . .
H19 H 0.3232 -0.1790 0.2258 0.051 Uiso 1 1 calc R . . . .
C34 C -0.18405(17) -0.3176(2) 0.31310(11) 0.0522(6) Uani 1 1 d . . . . .
H34 H -0.1633 -0.2834 0.3528 0.063 Uiso 1 1 calc R . . . .
C37 C -0.24524(14) -0.4243(2) 0.19617(10) 0.0472(5) Uani 1 1 d . . . . .
H37 H -0.2667 -0.4618 0.1574 0.057 Uiso 1 1 calc R . . . .
C17 C 0.44315(16) -0.4655(2) 0.21073(12) 0.0542(6) Uani 1 1 d . . . . .
H17 H 0.4682 -0.5386 0.2349 0.065 Uiso 1 1 calc R . . . .
C36 C -0.30940(16) -0.3581(3) 0.23660(12) 0.0595(6) Uani 1 1 d . . . . .
H36 H -0.3733 -0.3497 0.2241 0.071 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
N2 C12 1.363(2) . ?
N2 C10 1.334(2) . ?
N4 C5 1.382(2) . ?
N4 C13 1.329(2) . ?
N1 C11 1.362(2) . ?
N1 C1 1.330(2) . ?
N3 C6 1.394(2) . ?
N3 C13 1.390(2) . ?
N3 C14 1.449(2) . ?
C7 C6 1.444(2) . ?
C7 C12 1.431(2) . ?
C7 C8 1.410(2) . ?
C6 C5 1.384(2) . ?
C12 C11 1.473(2) . ?
C5 C4 1.436(2) . ?
C11 C4 1.420(2) . ?
C4 C3 1.410(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.400(3) . ?
C13 C20 1.481(2) . ?
C20 C21 1.401(2) . ?
C20 C25 1.404(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(3) . ?
C2 C1 1.403(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.375(2) . ?
C8 H8 0.9300 . ?
C3 H3 0.9300 . ?
N5 C26 1.428(2) . ?
N5 C32 1.440(2) . ?
N5 C23 1.419(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.386(2) . ?
C15 C16 1.395(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(3) . ?
C14 C19 1.397(3) . ?
C25 H25 0.9300 . ?
C25 C24 1.388(3) . ?
C1 H1 0.9300 . ?
C22 H22 0.9300 . ?
C22 C23 1.400(3) . ?
C26 C27 1.402(3) . ?
C26 C31 1.396(3) . ?
C24 H24 0.9300 . ?
C24 C23 1.400(3) . ?
C32 C33 1.393(3) . ?
C32 C37 1.385(3) . ?
C28 H28 0.9300 . ?
C28 C27 1.390(3) . ?
C28 C29 1.385(3) . ?
C27 H27 0.9300 . ?
C33 H33 0.9300 . ?
C33 C34 1.382(3) . ?
C31 H31 0.9300 . ?
C31 C30 1.392(3) . ?
C30 H30 0.9300 . ?
C30 C29 1.387(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(3) . ?
C18 C17 1.387(3) . ?
C29 H29 0.9300 . ?
C35 H35 0.9300 . ?
C35 C34 1.372(3) . ?
C35 C36 1.384(3) . ?
C19 H19 0.9300 . ?
C34 H34 0.9300 . ?
C37 H37 0.9300 . ?
C37 C36 1.395(3) . ?
C17 H17 0.9300 . ?
C36 H36 0.9300 . ?

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
C10 N2 C12 117.94(15) . . ?
C13 N4 C5 104.86(14) . . ?
C1 N1 C11 117.51(16) . . ?
C6 N3 C14 127.19(14) . . ?
C13 N3 C6 106.44(13) . . ?
C13 N3 C14 125.91(13) . . ?
C12 C7 C6 116.04(15) . . ?
C8 C7 C6 126.39(15) . . ?
C8 C7 C12 117.56(15) . . ?
N3 C6 C7 131.58(15) . . ?
C5 C6 N3 105.15(14) . . ?
C5 C6 C7 123.26(15) . . ?
N2 C12 C7 122.12(15) . . ?
N2 C12 C11 116.86(15) . . ?
C7 C12 C11 121.01(15) . . ?
N4 C5 C6 111.47(15) . . ?
N4 C5 C4 126.98(14) . . ?
C6 C5 C4 121.51(15) . . ?
N1 C11 C12 117.70(15) . . ?
N1 C11 C4 121.99(15) . . ?
C4 C11 C12 120.30(14) . . ?
C11 C4 C5 117.87(14) . . ?
C3 C4 C5 123.48(15) . . ?
C3 C4 C11 118.65(15) . . ?
N2 C10 H10 118.1 . . ?
N2 C10 C9 123.84(16) . . ?
C9 C10 H10 118.1 . . ?
N4 C13 N3 112.07(14) . . ?
N4 C13 C20 122.00(15) . . ?
N3 C13 C20 125.83(14) . . ?
C21 C20 C13 125.36(16) . . ?
C21 C20 C25 117.55(16) . . ?
C25 C20 C13 117.09(15) . . ?
C3 C2 H2 120.6 . . ?
C3 C2 C1 118.86(17) . . ?
C1 C2 H2 120.6 . . ?
C10 C9 H9 120.5 . . ?
C8 C9 C10 118.92(16) . . ?
C8 C9 H9 120.5 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.61(16) . . ?
C9 C8 H8 120.2 . . ?
C4 C3 H3 120.7 . . ?
C2 C3 C4 118.63(17) . . ?
C2 C3 H3 120.7 . . ?
C26 N5 C32 119.27(14) . . ?
C23 N5 C26 122.52(15) . . ?
C23 N5 C32 118.18(15) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.21(18) . . ?
C16 C15 H15 120.4 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.96(17) . . ?
C22 C21 H21 119.5 . . ?
C15 C14 N3 120.24(16) . . ?
C15 C14 C19 121.40(16) . . ?
C19 C14 N3 118.34(16) . . ?
C20 C25 H25 119.2 . . ?
C24 C25 C20 121.65(16) . . ?
C24 C25 H25 119.2 . . ?
N1 C1 C2 124.33(17) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.25(17) . . ?
C23 C22 H22 119.4 . . ?
C27 C26 N5 120.97(17) . . ?
C31 C26 N5 120.18(18) . . ?
C31 C26 C27 118.83(17) . . ?
C25 C24 H24 119.8 . . ?
C25 C24 C23 120.34(17) . . ?
C23 C24 H24 119.8 . . ?
C33 C32 N5 119.57(17) . . ?
C37 C32 N5 121.26(17) . . ?
C37 C32 C33 119.15(18) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C29 C28 C27 120.5(2) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.37(18) . . ?
C28 C27 H27 119.8 . . ?
C32 C33 H33 119.9 . . ?
C34 C33 C32 120.25(19) . . ?
C34 C33 H33 119.9 . . ?
C26 C31 H31 119.9 . . ?
C30 C31 C26 120.1(2) . . ?
C30 C31 H31 119.9 . . ?
C31 C30 H30 119.6 . . ?
C29 C30 C31 120.77(19) . . ?
C29 C30 H30 119.6 . . ?
C15 C16 H16 120.1 . . ?
C17 C16 C15 119.71(19) . . ?
C17 C16 H16 120.1 . . ?
C22 C23 N5 121.98(16) . . ?
C24 C23 N5 119.75(16) . . ?
C24 C23 C22 118.24(16) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.3(2) . . ?
C28 C29 C30 119.39(19) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C34 C35 H35 120.3 . . ?
C34 C35 C36 119.4(2) . . ?
C36 C35 H35 120.3 . . ?
C14 C19 H19 120.7 . . ?
C18 C19 C14 118.7(2) . . ?
C18 C19 H19 120.7 . . ?
C33 C34 H34 119.6 . . ?
C35 C34 C33 120.8(2) . . ?
C35 C34 H34 119.6 . . ?
C32 C37 H37 120.0 . . ?
C32 C37 C36 119.9(2) . . ?
C36 C37 H37 120.0 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.63(19) . . ?
C18 C17 H17 119.7 . . ?
C35 C36 C37 120.4(2) . . ?
C35 C36 H36 119.8 . . ?
C37 C36 H36 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C12 C11 N1 -0.1(2) . . . . ?
N2 C12 C11 C4 179.09(15) . . . . ?
N2 C10 C9 C8 -0.7(3) . . . . ?
N4 C5 C4 C11 178.25(16) . . . . ?
N4 C5 C4 C3 -0.8(3) . . . . ?
N4 C13 C20 C21 153.59(19) . . . . ?
N4 C13 C20 C25 -26.4(3) . . . . ?
N1 C11 C4 C5 179.02(16) . . . . ?
N1 C11 C4 C3 -1.9(2) . . . . ?
N3 C6 C5 N4 -0.18(19) . . . . ?
N3 C6 C5 C4 177.64(15) . . . . ?
N3 C13 C20 C21 -30.5(3) . . . . ?
N3 C13 C20 C25 149.55(18) . . . . ?
N3 C14 C19 C18 176.72(17) . . . . ?
C7 C6 C5 N4 -179.36(15) . . . . ?
C7 C6 C5 C4 -1.5(3) . . . . ?
C7 C12 C11 N1 -178.99(15) . . . . ?
C7 C12 C11 C4 0.2(2) . . . . ?
C6 N3 C13 N4 1.28(19) . . . . ?
C6 N3 C13 C20 -175.01(16) . . . . ?
C6 N3 C14 C15 -84.6(2) . . . . ?
C6 N3 C14 C19 96.6(2) . . . . ?
C6 C7 C12 N2 -179.65(15) . . . . ?
C6 C7 C12 C11 -0.8(2) . . . . ?
C6 C7 C8 C9 178.41(16) . . . . ?
C6 C5 C4 C11 0.8(2) . . . . ?
C6 C5 C4 C3 -178.26(17) . . . . ?
C12 N2 C10 C9 -0.3(3) . . . . ?
C12 C7 C6 N3 -177.42(17) . . . . ?
C12 C7 C6 C5 1.5(2) . . . . ?
C12 C7 C8 C9 -0.2(2) . . . . ?
C12 C11 C4 C5 -0.1(2) . . . . ?
C12 C11 C4 C3 178.95(15) . . . . ?
C5 N4 C13 N3 -1.36(19) . . . . ?
C5 N4 C13 C20 175.10(16) . . . . ?
C5 C4 C3 C2 179.96(17) . . . . ?
C11 N1 C1 C2 0.1(3) . . . . ?
C11 C4 C3 C2 0.9(3) . . . . ?
C10 N2 C12 C7 1.2(2) . . . . ?
C10 N2 C12 C11 -177.71(15) . . . . ?
C10 C9 C8 C7 1.0(3) . . . . ?
C13 N4 C5 C6 0.94(19) . . . . ?
C13 N4 C5 C4 -176.73(17) . . . . ?
C13 N3 C6 C7 178.45(17) . . . . ?
C13 N3 C6 C5 -0.62(18) . . . . ?
C13 N3 C14 C15 104.3(2) . . . . ?
C13 N3 C14 C19 -74.4(2) . . . . ?
C13 C20 C21 C22 179.42(19) . . . . ?
C13 C20 C25 C24 -179.76(18) . . . . ?
C20 C21 C22 C23 0.4(3) . . . . ?
C20 C25 C24 C23 0.3(3) . . . . ?
C8 C7 C6 N3 4.0(3) . . . . ?
C8 C7 C6 C5 -177.11(16) . . . . ?
C8 C7 C12 N2 -0.9(2) . . . . ?
C8 C7 C12 C11 177.92(15) . . . . ?
C3 C2 C1 N1 -1.1(3) . . . . ?
N5 C26 C27 C28 -177.85(16) . . . . ?
N5 C26 C31 C30 177.07(16) . . . . ?
N5 C32 C33 C34 177.72(17) . . . . ?
N5 C32 C37 C36 -176.41(19) . . . . ?
C15 C14 C19 C18 -2.0(3) . . . . ?
C15 C16 C17 C18 -2.0(3) . . . . ?
C21 C20 C25 C24 0.2(3) . . . . ?
C21 C22 C23 N5 -178.1(2) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C14 N3 C6 C7 6.0(3) . . . . ?
C14 N3 C6 C5 -173.08(15) . . . . ?
C14 N3 C13 N4 173.87(15) . . . . ?
C14 N3 C13 C20 -2.4(3) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C25 C20 C21 C22 -0.6(3) . . . . ?
C25 C24 C23 N5 177.77(18) . . . . ?
C25 C24 C23 C22 -0.5(3) . . . . ?
C1 N1 C11 C12 -179.47(16) . . . . ?
C1 N1 C11 C4 1.3(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C26 N5 C32 C33 121.23(19) . . . . ?
C26 N5 C32 C37 -60.7(3) . . . . ?
C26 N5 C23 C22 -34.4(3) . . . . ?
C26 N5 C23 C24 147.46(19) . . . . ?
C26 C31 C30 C29 0.9(3) . . . . ?
C32 N5 C26 C27 144.43(18) . . . . ?
C32 N5 C26 C31 -33.9(3) . . . . ?
C32 N5 C23 C22 147.4(2) . . . . ?
C32 N5 C23 C24 -30.8(3) . . . . ?
C32 C33 C34 C35 -1.0(3) . . . . ?
C32 C37 C36 C35 -1.6(3) . . . . ?
C27 C26 C31 C30 -1.3(3) . . . . ?
C27 C28 C29 C30 -1.1(3) . . . . ?
C33 C32 C37 C36 1.7(3) . . . . ?
C31 C26 C27 C28 0.5(3) . . . . ?
C31 C30 C29 C28 0.3(3) . . . . ?
C16 C15 C14 N3 -176.59(15) . . . . ?
C16 C15 C14 C19 2.2(3) . . . . ?
C23 N5 C26 C27 -33.8(3) . . . . ?
C23 N5 C26 C31 147.87(18) . . . . ?
C23 N5 C32 C33 -60.5(2) . . . . ?
C23 N5 C32 C37 117.6(2) . . . . ?
C29 C28 C27 C26 0.7(3) . . . . ?
C19 C18 C17 C16 2.1(3) . . . . ?
C34 C35 C36 C37 0.2(3) . . . . ?
C37 C32 C33 C34 -0.4(3) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C36 C35 C34 C33 1.1(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jcz_150429_sq
_audit_block_doi                 10.5517/ccdc.csd.cc1mg8kx
_database_code_depnum_ccdc_archive 'CCDC 1503269'
_audit_update_record             
;
2016-11-10 deposited with the CCDC.
2017-01-18 downloaded from the CCDC.
;
_audit_creation_date             2015-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C59 H37 F4 Ir N7, Cl'
_chemical_formula_sum            'C59 H37 Cl F4 Ir N7'
_chemical_formula_weight         1147.60
_chemical_melting_point          ?
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   20.8286(9)
_cell_length_b                   18.6390(6)
_cell_length_c                   17.8263(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.188(4)
_cell_angle_gamma                90
_cell_volume                     6919.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7897
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      70.1440
_cell_measurement_theta_min      3.1580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.461
_exptl_absorpt_correction_T_max  0.700
_exptl_absorpt_correction_T_min  0.470
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2280
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_standards_number         8047
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            32146
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.563
_diffrn_reflns_theta_min         2.122
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8047
_reflns_number_total             13180
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         2.541
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     616
_refine_ls_number_reflns         13180
_refine_ls_number_restraints     1381
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0745
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1180P)²+4.4707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C14A-C13 = C14-C13 = C16-C15A = C16-C15 = C17-C16 = C17-C12 = C13-C12
 1.388 with sigma of 0.02
 N7-C48 \\sim N7A-C48
 with sigma of 0.02
 N7A-C45A \\sim N7-C45
 with sigma of 0.02
 N7-C54 \\sim N7A-C54
 with sigma of 0.02
 F2A-C5A \\sim F2-C5
 with sigma of 0.02
 F4A-C14A \\sim F4-C14
 with sigma of 0.02
3. Restrained planarity
 C15A, C14A, C13, C12, C17, C15
 with sigma of 0.2
4. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(C1) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C4) \\sim
Ueq, Uanis(C5) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F1)
\\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(N1) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C9)
\\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C7) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(F4) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C17) \\sim Ueq,
Uanis(C12) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C55) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C59) \\sim Ueq, Uanis(C58)
\\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C56) \\sim Ueq: with sigma of 0.1 and
sigma for terminal atoms of 0.2
Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(F1) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
Uanis(F4A) \\sim Ueq, Uanis(F4) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
Uanis(C48) = Uanis(C49) = Uanis(C50) = Uanis(C51) = Uanis(C52) = Uanis(C53)
Uanis(C42A) = Uanis(C43A) = Uanis(C44A) = Uanis(C45A) = Uanis(C46A) =
Uanis(C47A)
Uanis(N7) = Uanis(N7A)
Uanis(C42) = Uanis(C43) = Uanis(C44) = Uanis(C45) = Uanis(C46) = Uanis(C47)
Uanis(C54) = Uanis(C55) = Uanis(C56) = Uanis(C57) = Uanis(C58) = Uanis(C59)
6. Others
 Sof(C43A)=Sof(C42A)=Sof(H42A)=Sof(C44A)=Sof(H44A)=Sof(C45A)=Sof(C46A)=
 Sof(H46A)=Sof(C47A)=Sof(H47A)=Sof(N7A)=1-FVAR(1)
 Sof(N7)=Sof(C46)=Sof(H46)=Sof(C47)=Sof(H47)=Sof(C42)=Sof(C43)=Sof(H43)=
 Sof(C44)=Sof(H44)=Sof(C45)=FVAR(1)
 Sof(H11A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(C6A)=Sof(C10A)=Sof(H10A)=Sof(C9A)=
 Sof(H9A)=Sof(C8A)=Sof(H8A)=Sof(C7A)=Sof(F2A)=1-FVAR(2)
 Sof(F2)=Sof(H11)=Sof(C10)=Sof(H10)=Sof(C9)=Sof(H9)=Sof(C8)=Sof(H8)=Sof(C7)=
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(C6)=FVAR(2)
 Sof(H13A)=Sof(C14A)=Sof(C15A)=Sof(H15A)=Sof(F4A)=1-FVAR(3)
 Sof(F4)=Sof(H13)=Sof(C14)=Sof(C15)=Sof(H15)=FVAR(3)
7.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C11(H11A), C10(H10), C9(H9), C8(H8), C2(H2), C4A(H4A), C4(H4),
 C13(H13A), C13(H13), C15A(H15A), C15(H15), C19(H19), C20(H20), C21(H21),
 C22(H22), C23(H23), C24(H24), C25(H25), C30(H30), C31(H31), C32(H32), C36(H36),
  C37(H37), C38(H38), C39(H39), C40(H40), C46(H46), C47(H47), C43(H43),
 C44(H44), C49(H49), C50(H50), C51(H51), C52(H52), C53(H53), C59(H59), C58(H58),
  C57(H57), C56(H56), C55(H55), C42A(H42A), C44A(H44A), C46A(H46A), C47A(H47A),
 C10A(H10A), C9A(H9A), C8A(H8A)
7.b Fitted hexagon refined as free rotating group:
 N1(C11,C10,C9,C8,C7), C2(C3,C4A,C5A,C6A,C1), C13(C14A,C15A,C16,C17,C12),
 C46(C47,C42,C43,C44,C45), C54(C59,C58,C57,C56,C55), C43A(C42A,C44A,C45A,C46A,
 C47A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.61728(2) 0.85821(2) 0.17358(2) 0.07400(17) Uani 1 1 d . U . . .
F1 F 0.8264(3) 1.0249(3) 0.2214(4) 0.1139(19) Uani 1 1 d . U . . .
F2 F 0.8558(6) 0.7773(7) 0.2389(12) 0.147(6) Uani 0.74(2) 1 d D U P A 1
F3 F 0.5950(5) 1.0121(4) -0.0729(4) 0.142(3) Uani 1 1 d . U . . .
F4 F 0.6749(19) 0.7903(14) -0.1160(14) 0.122(8) Uani 0.52(6) 1 d D U P B 1
N1 N 0.6564(3) 0.7574(3) 0.1834(4) 0.090(2) Uani 1 1 d . U . . .
C11 C 0.6200(3) 0.6956(3) 0.1722(4) 0.093(3) Uani 1 1 d G U . A .
H11 H 0.5777 0.6990 0.1551 0.112 Uiso 0.74(2) 1 calc R . P A 1
H11A H 0.5764 0.6968 0.1822 0.112 Uiso 0.26(2) 1 calc R . P A 2
C10 C 0.6471(5) 0.6287(3) 0.1866(7) 0.103(4) Uani 0.74(2) 1 d G U P A 1
H10 H 0.6228 0.5874 0.1792 0.123 Uiso 0.74(2) 1 calc R . P A 1
C9 C 0.7104(5) 0.6236(4) 0.2122(9) 0.110(5) Uani 0.74(2) 1 d G U P A 1
H9 H 0.7285 0.5788 0.2219 0.132 Uiso 0.74(2) 1 calc R . P A 1
C8 C 0.7467(4) 0.6854(5) 0.2234(9) 0.107(5) Uani 0.74(2) 1 d G U P A 1
H8 H 0.7891 0.6820 0.2405 0.129 Uiso 0.74(2) 1 calc R . P A 1
C7 C 0.7197(3) 0.7523(4) 0.2090(6) 0.091(4) Uani 0.74(2) 1 d G U P A 1
N2 N 0.5852(3) 0.9623(4) 0.1588(4) 0.0716(15) Uani 1 1 d . U . . .
N3 N 0.5836(3) 0.8452(4) 0.2854(4) 0.0705(15) Uani 1 1 d . U . . .
N4 N 0.5195(3) 0.8242(3) 0.1545(3) 0.0677(14) Uani 1 1 d . U . . .
N5 N 0.3915(4) 0.7582(3) 0.4114(3) 0.0701(15) Uani 1 1 d . U . . .
N6 N 0.3404(3) 0.7332(3) 0.3043(3) 0.0647(14) Uani 1 1 d . U . . .
N7 N 0.1525(14) 0.5903(12) 0.541(3) 0.152(4) Uani 0.381(13) 1 d D U P C 1
C2 C 0.7359(3) 0.9518(3) 0.2051(5) 0.082(2) Uani 1 1 d . U . . .
H2 H 0.7102 0.9925 0.2016 0.098 Uiso 1 1 calc R . . . .
C3 C 0.8019(3) 0.9588(5) 0.2159(7) 0.106(3) Uani 1 1 d G U . . .
C4A C 0.8404(4) 0.8980(7) 0.2211(18) 0.121(7) Uani 0.26(2) 1 d G U P A 2
H4A H 0.8845 0.9026 0.2283 0.145 Uiso 0.26(2) 1 calc R . P A 2
C5A C 0.8129(6) 0.8302(5) 0.216(2) 0.128(7) Uani 0.26(2) 1 d DG U P A 2
C6A C 0.7469(6) 0.8232(3) 0.2047(17) 0.109(6) Uani 0.26(2) 1 d G U P A 2
C1 C 0.7084(4) 0.8840(4) 0.1995(6) 0.086(2) Uani 1 1 d G U . . .
C4 C 0.8427(7) 0.9034(9) 0.2195(13) 0.119(5) Uani 0.74(2) 1 d . U P A 1
H4 H 0.8870 0.9100 0.2215 0.143 Uiso 0.74(2) 1 calc R . P A 1
C5 C 0.8153(8) 0.8356(9) 0.2201(17) 0.136(5) Uani 0.74(2) 1 d D U P A 1
C6 C 0.7515(7) 0.8235(7) 0.2071(12) 0.108(4) Uani 0.74(2) 1 d . U P A 1
C13 C 0.6614(4) 0.8210(3) 0.0153(4) 0.109(3) Uani 1 1 d D U . . .
H13A H 0.6762 0.7775 0.0345 0.131 Uiso 0.48(6) 1 calc R . P B 2
H13 H 0.6784 0.7775 0.0319 0.131 Uiso 0.52(6) 1 calc R . P B 1
C14A C 0.6654(8) 0.8351(5) -0.0610(4) 0.124(6) Uani 0.48(6) 1 d DG U P B 2
C15A C 0.6432(8) 0.9001(5) -0.0898(3) 0.131(6) Uani 0.48(6) 1 d DG U P B 2
H15A H 0.6459 0.9095 -0.1409 0.157 Uiso 0.48(6) 1 calc R . P B 2
C16 C 0.6170(5) 0.9508(4) -0.0423(4) 0.113(3) Uani 1 1 d DG U . B .
C17 C 0.6129(4) 0.9367(3) 0.0340(3) 0.092(3) Uani 1 1 d DG U . B .
C12 C 0.6351(4) 0.8718(3) 0.0628(3) 0.083(2) Uani 1 1 d DG U . B .
C14 C 0.6596(17) 0.8418(13) -0.0594(9) 0.124(6) Uani 0.52(6) 1 d D U P B 1
C15 C 0.6406(15) 0.9008(11) -0.0919(13) 0.131(6) Uani 0.52(6) 1 d D U P B 1
H15 H 0.6428 0.9085 -0.1434 0.157 Uiso 0.52(6) 1 calc R . P B 1
C18 C 0.5847(5) 0.9882(4) 0.0869(5) 0.085(2) Uani 1 1 d . U . . .
C19 C 0.5624(6) 1.0558(5) 0.0731(6) 0.103(3) Uani 1 1 d . U . . .
H19 H 0.5638 1.0744 0.0247 0.124 Uiso 1 1 calc R . . . .
C20 C 0.5377(6) 1.0967(5) 0.1301(7) 0.100(3) Uani 1 1 d . U . . .
H20 H 0.5208 1.1420 0.1198 0.120 Uiso 1 1 calc R . . . .
C21 C 0.5380(5) 1.0705(4) 0.2018(6) 0.087(2) Uani 1 1 d . U . . .
H21 H 0.5225 1.0978 0.2411 0.104 Uiso 1 1 calc R . . . .
C22 C 0.5619(4) 1.0027(4) 0.2141(5) 0.076(2) Uani 1 1 d . U . . .
H22 H 0.5619 0.9842 0.2626 0.091 Uiso 1 1 calc R . . . .
C23 C 0.6143(5) 0.8577(5) 0.3495(5) 0.083(2) Uani 1 1 d . U . . .
H23 H 0.6559 0.8755 0.3479 0.100 Uiso 1 1 calc R . . . .
C24 C 0.5880(5) 0.8458(6) 0.4190(5) 0.094(3) Uani 1 1 d . U . . .
H24 H 0.6121 0.8546 0.4625 0.113 Uiso 1 1 calc R . . . .
C25 C 0.5280(5) 0.8219(6) 0.4234(5) 0.083(2) Uani 1 1 d . U . . .
H25 H 0.5095 0.8148 0.4699 0.100 Uiso 1 1 calc R . . . .
C26 C 0.4926(4) 0.8075(4) 0.3563(4) 0.0678(17) Uani 1 1 d . U . . .
C27 C 0.5217(4) 0.8195(4) 0.2872(4) 0.0629(15) Uani 1 1 d . U . . .
C28 C 0.4864(4) 0.8096(4) 0.2173(4) 0.0624(15) Uani 1 1 d . U . . .
C29 C 0.4243(4) 0.7842(4) 0.2145(4) 0.0602(15) Uani 1 1 d . U . . .
C30 C 0.3915(4) 0.7835(4) 0.1438(4) 0.0669(18) Uani 1 1 d . U . . .
H30 H 0.3483 0.7712 0.1393 0.080 Uiso 1 1 calc R . . . .
C31 C 0.4268(5) 0.8020(4) 0.0823(4) 0.075(2) Uani 1 1 d . U . . .
H31 H 0.4071 0.8014 0.0350 0.090 Uiso 1 1 calc R . . . .
C32 C 0.4891(5) 0.8209(4) 0.0887(4) 0.0740(19) Uani 1 1 d . U . . .
H32 H 0.5115 0.8320 0.0456 0.089 Uiso 1 1 calc R . . . .
C33 C 0.4294(4) 0.7792(4) 0.3534(3) 0.0580(14) Uani 1 1 d . U . . .
C34 C 0.3974(4) 0.7654(4) 0.2853(4) 0.0612(15) Uani 1 1 d . U . . .
C35 C 0.2912(4) 0.7078(4) 0.2538(4) 0.0690(17) Uani 1 1 d . U . . .
C36 C 0.3047(5) 0.6534(5) 0.2039(4) 0.077(2) Uani 1 1 d . U . . .
H36 H 0.3454 0.6330 0.2025 0.092 Uiso 1 1 calc R . . . .
C37 C 0.2549(6) 0.6298(6) 0.1554(5) 0.098(3) Uani 1 1 d . U . . .
H37 H 0.2620 0.5928 0.1216 0.118 Uiso 1 1 calc R . . . .
C38 C 0.1961(6) 0.6614(8) 0.1584(7) 0.112(3) Uani 1 1 d . U . . .
H38 H 0.1640 0.6471 0.1246 0.134 Uiso 1 1 calc R . . . .
C39 C 0.1829(6) 0.7138(7) 0.2097(7) 0.110(3) Uani 1 1 d . U . . .
H39 H 0.1415 0.7320 0.2132 0.132 Uiso 1 1 calc R . . . .
C40 C 0.2305(5) 0.7389(6) 0.2550(5) 0.088(2) Uani 1 1 d . U . . .
H40 H 0.2227 0.7770 0.2872 0.105 Uiso 1 1 calc R . . . .
C41 C 0.3390(5) 0.7289(4) 0.3809(4) 0.0702(18) Uani 1 1 d . U . . .
C46 C 0.2437(10) 0.6712(9) 0.5470(9) 0.087(3) Uani 0.381(13) 1 d . U P C 1
H46 H 0.2300 0.6886 0.5929 0.104 Uiso 0.381(13) 1 calc R . P C 1
C47 C 0.2774(13) 0.7156(8) 0.4991(11) 0.087(3) Uani 0.381(13) 1 d G U P C 1
H47 H 0.2861 0.7628 0.5129 0.104 Uiso 0.381(13) 1 calc R . P C 1
C42 C 0.2979(12) 0.6896(10) 0.4306(11) 0.087(3) Uani 0.381(13) 1 d G U P C 1
C43 C 0.2847(10) 0.6191(10) 0.4100(8) 0.087(3) Uani 0.381(13) 1 d G U P C 1
H43 H 0.2984 0.6017 0.3642 0.104 Uiso 0.381(13) 1 calc R . P C 1
C44 C 0.2511(11) 0.5746(8) 0.4579(8) 0.087(3) Uani 0.381(13) 1 d G U P C 1
H44 H 0.2423 0.5275 0.4441 0.104 Uiso 0.381(13) 1 calc R . P C 1
C45 C 0.2306(9) 0.6007(9) 0.5265(8) 0.087(3) Uani 0.381(13) 1 d DG U P C 1
C48 C 0.0975(8) 0.6337(11) 0.5885(10) 0.158(2) Uani 1 1 d D U . . .
C49 C 0.0765(7) 0.5976(11) 0.6553(9) 0.158(2) Uani 1 1 d . U . . .
H49 H 0.0924 0.5527 0.6686 0.190 Uiso 1 1 calc R . . . .
C50 C 0.0315(7) 0.6326(11) 0.6993(10) 0.158(2) Uani 1 1 d . U . . .
H50 H 0.0166 0.6127 0.7435 0.190 Uiso 1 1 calc R . . . .
C51 C 0.0100(7) 0.6993(11) 0.6731(10) 0.158(2) Uani 1 1 d . U . . .
H51 H -0.0207 0.7236 0.7005 0.190 Uiso 1 1 calc R . . . .
C52 C 0.0320(7) 0.7309(11) 0.6086(9) 0.158(2) Uani 1 1 d . U . . .
H52 H 0.0170 0.7762 0.5954 0.190 Uiso 1 1 calc R . . . .
C53 C 0.0769(7) 0.6967(11) 0.5619(10) 0.158(2) Uani 1 1 d . U . . .
H53 H 0.0906 0.7163 0.5170 0.190 Uiso 1 1 calc R . . . .
C54 C 0.1383(7) 0.5133(6) 0.5306(8) 0.214(3) Uani 1 1 d D U . . .
C59 C 0.0822(7) 0.4926(7) 0.4928(8) 0.214(3) Uani 1 1 d G U . C .
H59 H 0.0525 0.5271 0.4773 0.257 Uiso 1 1 calc R . . . .
C58 C 0.0706(6) 0.4205(8) 0.4782(7) 0.214(3) Uani 1 1 d G U . C .
H58 H 0.0331 0.4066 0.4530 0.257 Uiso 1 1 calc R . . . .
C57 C 0.1151(7) 0.3690(6) 0.5014(8) 0.214(3) Uani 1 1 d G U . C .
H57 H 0.1073 0.3207 0.4917 0.257 Uiso 1 1 calc R . . . .
C56 C 0.1711(7) 0.3897(7) 0.5392(9) 0.214(3) Uani 1 1 d G U . C .
H56 H 0.2008 0.3553 0.5547 0.257 Uiso 1 1 calc R . . . .
C55 C 0.1827(6) 0.4618(8) 0.5538(7) 0.214(3) Uani 1 1 d G U . C .
H55 H 0.2202 0.4757 0.5791 0.257 Uiso 1 1 calc R . . . .
Cl1 Cl 0.4825(5) 0.6227(6) 0.1203(4) 0.279(4) Uani 1 1 d . U . . .
C43A C 0.2863(6) 0.6946(7) 0.4209(7) 0.080(2) Uani 0.619(13) 1 d . U P C 2
C42A C 0.2564(6) 0.6329(6) 0.3940(5) 0.080(2) Uani 0.619(13) 1 d G U P C 2
H42A H 0.2679 0.6137 0.3480 0.096 Uiso 0.619(13) 1 calc R . P C 2
C44A C 0.2093(6) 0.5997(5) 0.4358(5) 0.080(2) Uani 0.619(13) 1 d G U P C 2
H44A H 0.1892 0.5584 0.4178 0.096 Uiso 0.619(13) 1 calc R . P C 2
C45A C 0.1921(6) 0.6283(6) 0.5046(5) 0.080(2) Uani 0.619(13) 1 d DG U P C 2
C46A C 0.2220(6) 0.6900(5) 0.5315(5) 0.080(2) Uani 0.619(13) 1 d G U P C 2
H46A H 0.2105 0.7092 0.5775 0.096 Uiso 0.619(13) 1 calc R . P C 2
C47A C 0.2691(7) 0.7232(6) 0.4897(7) 0.080(2) Uani 0.619(13) 1 d G U P C 2
H47A H 0.2892 0.7645 0.5077 0.096 Uiso 0.619(13) 1 calc R . P C 2
N7A N 0.1511(10) 0.5820(9) 0.5596(14) 0.152(4) Uani 0.619(13) 1 d D U P C 2
C10A C 0.647(2) 0.632(2) 0.147(3) 0.096(8) Uani 0.26(2) 1 d . U P A 2
H10A H 0.6232 0.5967 0.1216 0.116 Uiso 0.26(2) 1 calc R . P A 2
C9A C 0.709(2) 0.627(2) 0.162(3) 0.094(8) Uani 0.26(2) 1 d . U P A 2
H9A H 0.7287 0.5824 0.1648 0.113 Uiso 0.26(2) 1 calc R . P A 2
C8A C 0.744(2) 0.689(2) 0.173(3) 0.092(7) Uani 0.26(2) 1 d . U P A 2
H8A H 0.7883 0.6846 0.1796 0.110 Uiso 0.26(2) 1 calc R . P A 2
C7A C 0.716(2) 0.760(2) 0.174(3) 0.095(7) Uani 0.26(2) 1 d . U P A 2
F2A F 0.8547(14) 0.7796(16) 0.185(2) 0.104(9) Uani 0.26(2) 1 d D U P A 2
F4A F 0.706(2) 0.7825(12) -0.096(2) 0.126(9) Uani 0.48(6) 1 d D U P B 2


_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 2.054(5) . ?
Ir1 N2 2.067(7) . ?
Ir1 N3 2.140(6) . ?
Ir1 N4 2.154(7) . ?
Ir1 C1 2.003(7) . ?
Ir1 C12 2.032(5) . ?
F1 C3 1.338(9) . ?
F2 C5 1.412(18) . ?
F3 C16 1.342(10) . ?
F4 C14 1.434(17) . ?
N1 C11 1.3900 . ?
N1 C7 1.3900 . ?
N1 C7A 1.26(5) . ?
C11 H11 0.9300 . ?
C11 H11A 0.9300 . ?
C11 C10 1.3900 . ?
C11 C10A 1.39(4) . ?
C10 H10 0.9300 . ?
C10 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C7 1.3900 . ?
C7 C6 1.483(15) . ?
N2 C18 1.370(11) . ?
N2 C22 1.340(11) . ?
N3 C23 1.319(11) . ?
N3 C27 1.377(11) . ?
N4 C28 1.354(9) . ?
N4 C32 1.322(10) . ?
N5 C33 1.372(9) . ?
N5 C41 1.329(11) . ?
N6 C34 1.378(10) . ?
N6 C35 1.432(11) . ?
N6 C41 1.368(9) . ?
N7 C45 1.66(2) . ?
N7 C48 1.65(2) . ?
N7 C54 1.48(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.3900 . ?
C2 C1 1.3900 . ?
C3 C4A 1.3900 . ?
C3 C4 1.338(19) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.3900 . ?
C5A C6A 1.3900 . ?
C5A F2A 1.40(2) . ?
C6A C1 1.3900 . ?
C6A C7A 1.44(5) . ?
C1 C6 1.446(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.39(2) . ?
C5 C6 1.36(2) . ?
C13 H13A 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14A 1.3900 . ?
C13 C12 1.3900 . ?
C13 C14 1.386(17) . ?
C14A C15A 1.3900 . ?
C14A F4A 1.437(18) . ?
C15A H15A 0.9300 . ?
C15A C16 1.3900 . ?
C16 C17 1.3900 . ?
C16 C15 1.384(16) . ?
C17 C12 1.3900 . ?
C17 C18 1.475(10) . ?
C14 C15 1.30(3) . ?
C15 H15 0.9300 . ?
C18 C19 1.364(14) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(15) . ?
C20 H20 0.9300 . ?
C20 C21 1.369(14) . ?
C21 H21 0.9300 . ?
C21 C22 1.374(12) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.382(14) . ?
C24 H24 0.9300 . ?
C24 C25 1.331(14) . ?
C25 H25 0.9300 . ?
C25 C26 1.417(12) . ?
C26 C27 1.403(10) . ?
C26 C33 1.418(12) . ?
C27 C28 1.445(10) . ?
C28 C29 1.377(11) . ?
C29 C30 1.421(11) . ?
C29 C34 1.434(9) . ?
C30 H30 0.9300 . ?
C30 C31 1.378(11) . ?
C31 H31 0.9300 . ?
C31 C32 1.348(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.396(10) . ?
C35 C36 1.381(11) . ?
C35 C40 1.391(13) . ?
C36 H36 0.9300 . ?
C36 C37 1.407(14) . ?
C37 H37 0.9300 . ?
C37 C38 1.361(18) . ?
C38 H38 0.9300 . ?
C38 C39 1.369(18) . ?
C39 H39 0.9300 . ?
C39 C40 1.350(15) . ?
C40 H40 0.9300 . ?
C41 C42 1.445(14) . ?
C41 C43A 1.468(11) . ?
C46 H46 0.9300 . ?
C46 C47 1.3900 . ?
C46 C45 1.3900 . ?
C47 H47 0.9300 . ?
C47 C42 1.3900 . ?
C42 C43 1.3900 . ?
C43 H43 0.9300 . ?
C43 C44 1.3900 . ?
C44 H44 0.9300 . ?
C44 C45 1.3900 . ?
C48 C49 1.44(2) . ?
C48 C53 1.33(2) . ?
C48 N7A 1.57(2) . ?
C49 H49 0.9300 . ?
C49 C50 1.40(2) . ?
C50 H50 0.9300 . ?
C50 C51 1.40(2) . ?
C51 H51 0.9300 . ?
C51 C52 1.38(2) . ?
C52 H52 0.9300 . ?
C52 C53 1.42(2) . ?
C53 H53 0.9300 . ?
C54 C59 1.3900 . ?
C54 C55 1.3900 . ?
C54 N7A 1.404(17) . ?
C59 H59 0.9300 . ?
C59 C58 1.3900 . ?
C58 H58 0.9300 . ?
C58 C57 1.3900 . ?
C57 H57 0.9300 . ?
C57 C56 1.3900 . ?
C56 H56 0.9300 . ?
C56 C55 1.3900 . ?
C55 H55 0.9300 . ?
C43A C42A 1.3900 . ?
C43A C47A 1.3900 . ?
C42A H42A 0.9300 . ?
C42A C44A 1.3900 . ?
C44A H44A 0.9300 . ?
C44A C45A 1.3900 . ?
C45A C46A 1.3900 . ?
C45A N7A 1.571(17) . ?
C46A H46A 0.9300 . ?
C46A C47A 1.3900 . ?
C47A H47A 0.9300 . ?
C10A H10A 0.9300 . ?
C10A C9A 1.32(6) . ?
C9A H9A 0.9300 . ?
C9A C8A 1.38(5) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.46(5) . ?

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 N2 175.0(2) . . ?
N1 Ir1 N3 87.3(3) . . ?
N1 Ir1 N4 96.6(2) . . ?
N2 Ir1 N3 96.5(3) . . ?
N2 Ir1 N4 87.4(3) . . ?
N3 Ir1 N4 77.7(2) . . ?
C1 Ir1 N1 80.1(3) . . ?
C1 Ir1 N2 96.1(3) . . ?
C1 Ir1 N3 98.0(3) . . ?
C1 Ir1 N4 174.8(3) . . ?
C1 Ir1 C12 90.2(4) . . ?
C12 Ir1 N1 96.7(3) . . ?
C12 Ir1 N2 79.9(3) . . ?
C12 Ir1 N3 171.4(3) . . ?
C12 Ir1 N4 94.2(3) . . ?
C11 N1 Ir1 122.2(4) . . ?
C11 N1 C7 120.0 . . ?
C7 N1 Ir1 117.5(4) . . ?
C7A N1 Ir1 109.8(19) . . ?
C7A N1 C11 124(2) . . ?
N1 C11 H11 120.0 . . ?
N1 C11 H11A 118.9 . . ?
C10 C11 N1 120.0 . . ?
C10 C11 H11 120.0 . . ?
C10A C11 N1 122(2) . . ?
C10A C11 H11A 118.9 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C7 C8 H8 120.0 . . ?
N1 C7 C6 110.6(8) . . ?
C8 C7 N1 120.0 . . ?
C8 C7 C6 128.9(8) . . ?
C18 N2 Ir1 116.5(6) . . ?
C22 N2 Ir1 123.7(6) . . ?
C22 N2 C18 119.7(7) . . ?
C23 N3 Ir1 128.7(6) . . ?
C23 N3 C27 118.6(7) . . ?
C27 N3 Ir1 112.7(5) . . ?
C28 N4 Ir1 115.1(5) . . ?
C32 N4 Ir1 125.9(5) . . ?
C32 N4 C28 118.8(7) . . ?
C41 N5 C33 106.9(6) . . ?
C34 N6 C35 126.8(6) . . ?
C41 N6 C34 107.9(7) . . ?
C41 N6 C35 125.3(7) . . ?
C48 N7 C45 135.9(18) . . ?
C54 N7 C45 106.6(15) . . ?
C54 N7 C48 113.8(13) . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C1 120.0 . . ?
C1 C2 H2 120.0 . . ?
F1 C3 C2 118.1(7) . . ?
F1 C3 C4A 121.9(7) . . ?
F1 C3 C4 117.8(9) . . ?
C4A C3 C2 120.0 . . ?
C4 C3 C2 124.1(9) . . ?
C3 C4A H4A 120.0 . . ?
C3 C4A C5A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A C6A 120.0 . . ?
C4A C5A F2A 112.3(17) . . ?
C6A C5A F2A 120.3(18) . . ?
C5A C6A C7A 124.2(19) . . ?
C1 C6A C5A 120.0 . . ?
C1 C6A C7A 113(2) . . ?
C2 C1 Ir1 128.5(5) . . ?
C2 C1 C6 116.6(8) . . ?
C6A C1 Ir1 111.2(5) . . ?
C6A C1 C2 120.0 . . ?
C6 C1 Ir1 114.7(7) . . ?
C3 C4 H4 121.9 . . ?
C3 C4 C5 116.2(13) . . ?
C5 C4 H4 121.9 . . ?
C4 C5 F2 117.3(15) . . ?
C6 C5 F2 119.3(15) . . ?
C6 C5 C4 123.4(15) . . ?
C1 C6 C7 115.1(11) . . ?
C5 C6 C7 125.3(13) . . ?
C5 C6 C1 119.2(12) . . ?
C14A C13 H13A 120.0 . . ?
C14A C13 C12 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13 123.5 . . ?
C14 C13 H13 123.5 . . ?
C14 C13 C12 113.1(11) . . ?
C13 C14A F4A 109.8(17) . . ?
C15A C14A C13 120.0 . . ?
C15A C14A F4A 128.9(14) . . ?
C14A C15A H15A 120.0 . . ?
C14A C15A C16 120.0 . . ?
C16 C15A H15A 120.0 . . ?
F3 C16 C15A 117.8(6) . . ?
F3 C16 C17 122.2(6) . . ?
F3 C16 C15 115.9(13) . . ?
C15A C16 C17 120.0 . . ?
C15 C16 C17 121.8(12) . . ?
C16 C17 C12 120.0 . . ?
C16 C17 C18 122.3(5) . . ?
C12 C17 C18 117.7(5) . . ?
C13 C12 Ir1 126.1(3) . . ?
C17 C12 Ir1 113.6(3) . . ?
C17 C12 C13 120.0 . . ?
C13 C14 F4 119(2) . . ?
C15 C14 F4 109(2) . . ?
C15 C14 C13 132(2) . . ?
C16 C15 H15 123.4 . . ?
C14 C15 C16 113.2(19) . . ?
C14 C15 H15 123.4 . . ?
N2 C18 C17 111.9(7) . . ?
C19 C18 N2 119.4(9) . . ?
C19 C18 C17 128.6(8) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(9) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.7(9) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 120.9 . . ?
C20 C21 C22 118.3(9) . . ?
C22 C21 H21 120.9 . . ?
N2 C22 C21 122.3(9) . . ?
N2 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
N3 C23 H23 118.1 . . ?
N3 C23 C24 123.7(9) . . ?
C24 C23 H23 118.1 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.8(10) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 120.5 . . ?
C24 C25 C26 119.1(8) . . ?
C26 C25 H25 120.5 . . ?
C25 C26 C33 124.6(7) . . ?
C27 C26 C25 119.0(8) . . ?
C27 C26 C33 116.3(7) . . ?
N3 C27 C26 119.8(7) . . ?
N3 C27 C28 119.0(6) . . ?
C26 C27 C28 121.1(7) . . ?
N4 C28 C27 115.4(7) . . ?
N4 C28 C29 122.2(7) . . ?
C29 C28 C27 122.4(6) . . ?
C28 C29 C30 117.9(6) . . ?
C28 C29 C34 115.8(7) . . ?
C30 C29 C34 126.1(7) . . ?
C29 C30 H30 121.6 . . ?
C31 C30 C29 116.7(8) . . ?
C31 C30 H30 121.6 . . ?
C30 C31 H31 119.1 . . ?
C32 C31 C30 121.8(8) . . ?
C32 C31 H31 119.1 . . ?
N4 C32 C31 122.0(7) . . ?
N4 C32 H32 119.0 . . ?
C31 C32 H32 119.0 . . ?
N5 C33 C26 128.8(7) . . ?
N5 C33 C34 109.3(7) . . ?
C34 C33 C26 121.8(6) . . ?
N6 C34 C29 132.5(7) . . ?
N6 C34 C33 105.4(6) . . ?
C33 C34 C29 122.1(7) . . ?
C36 C35 N6 119.7(8) . . ?
C36 C35 C40 120.9(9) . . ?
C40 C35 N6 119.4(8) . . ?
C35 C36 H36 121.1 . . ?
C35 C36 C37 117.9(10) . . ?
C37 C36 H36 121.1 . . ?
C36 C37 H37 120.3 . . ?
C38 C37 C36 119.5(10) . . ?
C38 C37 H37 120.3 . . ?
C37 C38 H38 119.0 . . ?
C37 C38 C39 121.9(12) . . ?
C39 C38 H38 119.0 . . ?
C38 C39 H39 120.3 . . ?
C40 C39 C38 119.4(12) . . ?
C40 C39 H39 120.3 . . ?
C35 C40 H40 119.9 . . ?
C39 C40 C35 120.2(10) . . ?
C39 C40 H40 119.9 . . ?
N5 C41 N6 110.4(7) . . ?
N5 C41 C42 116.8(11) . . ?
N5 C41 C43A 126.7(8) . . ?
N6 C41 C42 131.9(12) . . ?
N6 C41 C43A 122.9(9) . . ?
C47 C46 H46 120.0 . . ?
C47 C46 C45 120.0 . . ?
C45 C46 H46 120.0 . . ?
C46 C47 H47 120.0 . . ?
C42 C47 C46 120.0 . . ?
C42 C47 H47 120.0 . . ?
C47 C42 C41 124.0(13) . . ?
C47 C42 C43 120.0 . . ?
C43 C42 C41 115.7(13) . . ?
C42 C43 H43 120.0 . . ?
C44 C43 C42 120.0 . . ?
C44 C43 H43 120.0 . . ?
C43 C44 H44 120.0 . . ?
C45 C44 C43 120.0 . . ?
C45 C44 H44 120.0 . . ?
C46 C45 N7 104.8(13) . . ?
C44 C45 N7 114.8(16) . . ?
C44 C45 C46 120.0 . . ?
C49 C48 N7 115(2) . . ?
C49 C48 N7A 102.4(17) . . ?
C53 C48 N7 118(2) . . ?
C53 C48 C49 127.0(17) . . ?
C53 C48 N7A 130.6(16) . . ?
C48 C49 H49 121.2 . . ?
C50 C49 C48 117.7(19) . . ?
C50 C49 H49 121.2 . . ?
C49 C50 H50 121.9 . . ?
C49 C50 C51 116.2(17) . . ?
C51 C50 H50 121.9 . . ?
C50 C51 H51 118.4 . . ?
C52 C51 C50 123.2(17) . . ?
C52 C51 H51 118.4 . . ?
C51 C52 H52 118.9 . . ?
C51 C52 C53 122(2) . . ?
C53 C52 H52 118.9 . . ?
C48 C53 C52 113.5(17) . . ?
C48 C53 H53 123.2 . . ?
C52 C53 H53 123.2 . . ?
C59 C54 N7 120(2) . . ?
C59 C54 C55 120.0 . . ?
C59 C54 N7A 125.7(15) . . ?
C55 C54 N7 120(2) . . ?
C55 C54 N7A 113.5(16) . . ?
C54 C59 H59 120.0 . . ?
C54 C59 C58 120.0 . . ?
C58 C59 H59 120.0 . . ?
C59 C58 H58 120.0 . . ?
C57 C58 C59 120.0 . . ?
C57 C58 H58 120.0 . . ?
C58 C57 H57 120.0 . . ?
C58 C57 C56 120.0 . . ?
C56 C57 H57 120.0 . . ?
C57 C56 H56 120.0 . . ?
C55 C56 C57 120.0 . . ?
C55 C56 H56 120.0 . . ?
C54 C55 H55 120.0 . . ?
C56 C55 C54 120.0 . . ?
C56 C55 H55 120.0 . . ?
C42A C43A C41 121.8(8) . . ?
C42A C43A C47A 120.0 . . ?
C47A C43A C41 118.1(8) . . ?
C43A C42A H42A 120.0 . . ?
C43A C42A C44A 120.0 . . ?
C44A C42A H42A 120.0 . . ?
C42A C44A H44A 120.0 . . ?
C45A C44A C42A 120.0 . . ?
C45A C44A H44A 120.0 . . ?
C44A C45A N7A 119.5(8) . . ?
C46A C45A C44A 120.0 . . ?
C46A C45A N7A 119.0(9) . . ?
C45A C46A H46A 120.0 . . ?
C47A C46A C45A 120.0 . . ?
C47A C46A H46A 120.0 . . ?
C43A C47A H47A 120.0 . . ?
C46A C47A C43A 120.0 . . ?
C46A C47A H47A 120.0 . . ?
C48 N7A C45A 105.5(14) . . ?
C54 N7A C48 123.3(15) . . ?
C54 N7A C45A 111.9(14) . . ?
C11 C10A H10A 123.5 . . ?
C9A C10A C11 113(4) . . ?
C9A C10A H10A 123.5 . . ?
C10A C9A H9A 120.5 . . ?
C10A C9A C8A 119(4) . . ?
C8A C9A H9A 120.5 . . ?
C9A C8A H8A 118.1 . . ?
C9A C8A C7A 124(4) . . ?
C7A C8A H8A 118.1 . . ?
N1 C7A C6A 115(3) . . ?
N1 C7A C8A 111(3) . . ?
C6A C7A C8A 125(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 N1 C11 C10 -173.7(6) . . . . ?
Ir1 N1 C11 C10A 151(3) . . . . ?
Ir1 N1 C7 C8 174.0(5) . . . . ?
Ir1 N1 C7 C6 -13.5(10) . . . . ?
Ir1 N1 C7A C6A 37(5) . . . . ?
Ir1 N1 C7A C8A -174(3) . . . . ?
Ir1 N2 C18 C17 -4.6(10) . . . . ?
Ir1 N2 C18 C19 178.2(8) . . . . ?
Ir1 N2 C22 C21 -176.8(7) . . . . ?
Ir1 N3 C23 C24 -178.6(8) . . . . ?
Ir1 N3 C27 C26 179.5(5) . . . . ?
Ir1 N3 C27 C28 -4.1(8) . . . . ?
Ir1 N4 C28 C27 0.4(8) . . . . ?
Ir1 N4 C28 C29 -177.1(5) . . . . ?
Ir1 N4 C32 C31 -176.9(6) . . . . ?
Ir1 C1 C6 C7 -11(2) . . . . ?
Ir1 C1 C6 C5 176.0(16) . . . . ?
F1 C3 C4A C5A 179.6(10) . . . . ?
F1 C3 C4 C5 174.6(17) . . . . ?
F2 C5 C6 C7 -2(3) . . . . ?
F2 C5 C6 C1 170(2) . . . . ?
F3 C16 C17 C12 178.6(9) . . . . ?
F3 C16 C17 C18 -0.6(12) . . . . ?
F3 C16 C15 C14 -178(2) . . . . ?
F4 C14 C15 C16 172(3) . . . . ?
N1 C11 C10 C9 0.0 . . . . ?
N1 C11 C10A C9A 25(5) . . . . ?
N1 C7 C6 C1 15.7(19) . . . . ?
N1 C7 C6 C5 -171.9(18) . . . . ?
C11 N1 C7 C8 0.0 . . . . ?
C11 N1 C7 C6 172.5(10) . . . . ?
C11 N1 C7A C6A -166(2) . . . . ?
C11 N1 C7A C8A -17(5) . . . . ?
C11 C10 C9 C8 0.0 . . . . ?
C11 C10A C9A C8A -24(6) . . . . ?
C10 C9 C8 C7 0.0 . . . . ?
C9 C8 C7 N1 0.0 . . . . ?
C9 C8 C7 C6 -170.9(13) . . . . ?
C8 C7 C6 C1 -172.7(10) . . . . ?
C8 C7 C6 C5 0(2) . . . . ?
C7 N1 C11 C10 0.0 . . . . ?
N2 C18 C19 C20 -3.0(17) . . . . ?
N3 C23 C24 C25 -1.5(17) . . . . ?
N3 C27 C28 N4 2.5(10) . . . . ?
N3 C27 C28 C29 -180.0(7) . . . . ?
N4 C28 C29 C30 -9.2(11) . . . . ?
N4 C28 C29 C34 174.8(7) . . . . ?
N5 C33 C34 N6 -2.0(8) . . . . ?
N5 C33 C34 C29 177.7(6) . . . . ?
N5 C41 C42 C47 48.5(18) . . . . ?
N5 C41 C42 C43 -124.6(12) . . . . ?
N5 C41 C43A C42A -140.6(8) . . . . ?
N5 C41 C43A C47A 35.7(13) . . . . ?
N6 C35 C36 C37 179.8(7) . . . . ?
N6 C35 C40 C39 -177.6(9) . . . . ?
N6 C41 C42 C47 -143.5(12) . . . . ?
N6 C41 C42 C43 43(2) . . . . ?
N6 C41 C43A C42A 38.0(14) . . . . ?
N6 C41 C43A C47A -145.8(7) . . . . ?
N7 C48 C49 C50 177.8(19) . . . . ?
N7 C48 C53 C52 -177.0(19) . . . . ?
N7 C54 C59 C58 175.9(18) . . . . ?
N7 C54 C55 C56 -175.9(19) . . . . ?
C2 C3 C4A C5A 0.0 . . . . ?
C2 C3 C4 C5 -7(3) . . . . ?
C2 C1 C6 C7 173.8(10) . . . . ?
C2 C1 C6 C5 1(2) . . . . ?
C3 C2 C1 Ir1 -173.0(8) . . . . ?
C3 C2 C1 C6A 0.0 . . . . ?
C3 C2 C1 C6 1.3(19) . . . . ?
C3 C4A C5A C6A 0.0 . . . . ?
C3 C4A C5A F2A 150(3) . . . . ?
C3 C4 C5 F2 -168(2) . . . . ?
C3 C4 C5 C6 9(3) . . . . ?
C4A C5A C6A C1 0.0 . . . . ?
C4A C5A C6A C7A 159(3) . . . . ?
C5A C6A C1 Ir1 174.1(7) . . . . ?
C5A C6A C1 C2 0.0 . . . . ?
C5A C6A C7A N1 165(3) . . . . ?
C5A C6A C7A C8A 21(6) . . . . ?
C1 C2 C3 F1 -179.7(10) . . . . ?
C1 C2 C3 C4A 0.0 . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C1 C6A C7A N1 -35(5) . . . . ?
C1 C6A C7A C8A -179(4) . . . . ?
C4 C5 C6 C7 -178.5(19) . . . . ?
C4 C5 C6 C1 -6(3) . . . . ?
C13 C14A C15A C16 0.0 . . . . ?
C13 C14 C15 C16 -1(5) . . . . ?
C14A C13 C12 Ir1 174.0(7) . . . . ?
C14A C13 C12 C17 0.0 . . . . ?
C14A C15A C16 F3 -178.7(9) . . . . ?
C14A C15A C16 C17 0.0 . . . . ?
C15A C16 C17 C12 0.0 . . . . ?
C15A C16 C17 C18 -179.1(9) . . . . ?
C16 C17 C12 Ir1 -174.7(7) . . . . ?
C16 C17 C12 C13 0.0 . . . . ?
C16 C17 C18 N2 179.2(7) . . . . ?
C16 C17 C18 C19 -3.9(15) . . . . ?
C17 C16 C15 C14 -2(3) . . . . ?
C17 C18 C19 C20 -179.7(10) . . . . ?
C12 C13 C14A C15A 0.0 . . . . ?
C12 C13 C14A F4A 168(2) . . . . ?
C12 C13 C14 F4 -170(2) . . . . ?
C12 C13 C14 C15 4(4) . . . . ?
C12 C17 C18 N2 0.0(10) . . . . ?
C12 C17 C18 C19 177.0(10) . . . . ?
C14 C13 C12 Ir1 171.5(17) . . . . ?
C14 C13 C12 C17 -2.5(19) . . . . ?
C15 C16 C17 C12 2(2) . . . . ?
C15 C16 C17 C18 -176.8(19) . . . . ?
C18 N2 C22 C21 -0.9(13) . . . . ?
C18 C17 C12 Ir1 4.5(7) . . . . ?
C18 C17 C12 C13 179.2(9) . . . . ?
C18 C19 C20 C21 2.7(18) . . . . ?
C19 C20 C21 C22 -1.5(16) . . . . ?
C20 C21 C22 N2 0.6(14) . . . . ?
C22 N2 C18 C17 179.3(7) . . . . ?
C22 N2 C18 C19 2.0(14) . . . . ?
C23 N3 C27 C26 0.1(11) . . . . ?
C23 N3 C27 C28 176.5(7) . . . . ?
C23 C24 C25 C26 1.4(16) . . . . ?
C24 C25 C26 C27 -0.7(14) . . . . ?
C24 C25 C26 C33 177.4(9) . . . . ?
C25 C26 C27 N3 -0.1(11) . . . . ?
C25 C26 C27 C28 -176.4(7) . . . . ?
C25 C26 C33 N5 -2.7(13) . . . . ?
C25 C26 C33 C34 -179.2(8) . . . . ?
C26 C27 C28 N4 178.9(7) . . . . ?
C26 C27 C28 C29 -3.6(11) . . . . ?
C26 C33 C34 N6 175.1(6) . . . . ?
C26 C33 C34 C29 -5.2(11) . . . . ?
C27 N3 C23 C24 0.7(14) . . . . ?
C27 C26 C33 N5 175.4(7) . . . . ?
C27 C26 C33 C34 -1.1(10) . . . . ?
C27 C28 C29 C30 173.4(7) . . . . ?
C27 C28 C29 C34 -2.5(10) . . . . ?
C28 N4 C32 C31 -1.5(12) . . . . ?
C28 C29 C30 C31 6.0(10) . . . . ?
C28 C29 C34 N6 -173.5(7) . . . . ?
C28 C29 C34 C33 6.8(10) . . . . ?
C29 C30 C31 C32 -1.0(12) . . . . ?
C30 C29 C34 N6 10.9(13) . . . . ?
C30 C29 C34 C33 -168.7(7) . . . . ?
C30 C31 C32 N4 -1.3(13) . . . . ?
C32 N4 C28 C27 -175.5(7) . . . . ?
C32 N4 C28 C29 7.0(11) . . . . ?
C33 N5 C41 N6 -2.7(9) . . . . ?
C33 N5 C41 C42 167.8(12) . . . . ?
C33 N5 C41 C43A 176.0(9) . . . . ?
C33 C26 C27 N3 -178.3(7) . . . . ?
C33 C26 C27 C28 5.4(10) . . . . ?
C34 N6 C35 C36 62.3(10) . . . . ?
C34 N6 C35 C40 -116.9(9) . . . . ?
C34 N6 C41 N5 1.4(9) . . . . ?
C34 N6 C41 C42 -167.1(15) . . . . ?
C34 N6 C41 C43A -177.3(9) . . . . ?
C34 C29 C30 C31 -178.5(7) . . . . ?
C35 N6 C34 C29 1.3(13) . . . . ?
C35 N6 C34 C33 -179.0(7) . . . . ?
C35 N6 C41 N5 -179.2(7) . . . . ?
C35 N6 C41 C42 12.3(19) . . . . ?
C35 N6 C41 C43A 2.1(13) . . . . ?
C35 C36 C37 C38 0.9(14) . . . . ?
C36 C35 C40 C39 3.1(13) . . . . ?
C36 C37 C38 C39 -2.9(17) . . . . ?
C37 C38 C39 C40 5.1(18) . . . . ?
C38 C39 C40 C35 -5.1(16) . . . . ?
C40 C35 C36 C37 -1.0(12) . . . . ?
C41 N5 C33 C26 -174.0(7) . . . . ?
C41 N5 C33 C34 2.9(8) . . . . ?
C41 N6 C34 C29 -179.3(8) . . . . ?
C41 N6 C34 C33 0.4(8) . . . . ?
C41 N6 C35 C36 -116.9(8) . . . . ?
C41 N6 C35 C40 63.8(11) . . . . ?
C41 C42 C43 C44 173(2) . . . . ?
C41 C43A C42A C44A 176.2(12) . . . . ?
C41 C43A C47A C46A -176.3(12) . . . . ?
C46 C47 C42 C41 -173(2) . . . . ?
C46 C47 C42 C43 0.0 . . . . ?
C47 C46 C45 N7 -131(2) . . . . ?
C47 C46 C45 C44 0.0 . . . . ?
C47 C42 C43 C44 0.0 . . . . ?
C42 C43 C44 C45 0.0 . . . . ?
C43 C44 C45 N7 126(2) . . . . ?
C43 C44 C45 C46 0.0 . . . . ?
C45 N7 C48 C49 -109(4) . . . . ?
C45 N7 C48 C53 72(5) . . . . ?
C45 N7 C54 C59 -139(2) . . . . ?
C45 N7 C54 C55 37(3) . . . . ?
C45 C46 C47 C42 0.0 . . . . ?
C48 N7 C45 C46 -16(5) . . . . ?
C48 N7 C45 C44 -150(4) . . . . ?
C48 N7 C54 C59 59(4) . . . . ?
C48 N7 C54 C55 -125(3) . . . . ?
C48 C49 C50 C51 1(2) . . . . ?
C49 C48 C53 C52 3(3) . . . . ?
C49 C48 N7A C54 69(3) . . . . ?
C49 C48 N7A C45A -161.2(15) . . . . ?
C49 C50 C51 C52 -1(3) . . . . ?
C50 C51 C52 C53 2(3) . . . . ?
C51 C52 C53 C48 -3(3) . . . . ?
C53 C48 C49 C50 -3(3) . . . . ?
C53 C48 N7A C54 -114(2) . . . . ?
C53 C48 N7A C45A 16(3) . . . . ?
C54 N7 C45 C46 -172(2) . . . . ?
C54 N7 C45 C44 54(3) . . . . ?
C54 N7 C48 C49 46(4) . . . . ?
C54 N7 C48 C53 -133(3) . . . . ?
C54 C59 C58 C57 0.0 . . . . ?
C59 C54 C55 C56 0.0 . . . . ?
C59 C54 N7A C48 30(3) . . . . ?
C59 C54 N7A C45A -97.2(16) . . . . ?
C59 C58 C57 C56 0.0 . . . . ?
C58 C57 C56 C55 0.0 . . . . ?
C57 C56 C55 C54 0.0 . . . . ?
C55 C54 C59 C58 0.0 . . . . ?
C55 C54 N7A C48 -139(2) . . . . ?
C55 C54 N7A C45A 93.3(19) . . . . ?
C43A C42A C44A C45A 0.0 . . . . ?
C42A C43A C47A C46A 0.0 . . . . ?
C42A C44A C45A C46A 0.0 . . . . ?
C42A C44A C45A N7A -166.0(15) . . . . ?
C44A C45A C46A C47A 0.0 . . . . ?
C44A C45A N7A C48 -134.8(12) . . . . ?
C44A C45A N7A C54 2(2) . . . . ?
C45A C46A C47A C43A 0.0 . . . . ?
C46A C45A N7A C48 59(2) . . . . ?
C46A C45A N7A C54 -164.5(15) . . . . ?
C47A C43A C42A C44A 0.0 . . . . ?
N7A C48 C49 C50 175.0(16) . . . . ?
N7A C48 C53 C52 -173.5(18) . . . . ?
N7A C54 C59 C58 -168.9(16) . . . . ?
N7A C54 C55 C56 170.2(13) . . . . ?
N7A C45A C46A C47A 166.1(14) . . . . ?
C10A C9A C8A C7A 5(7) . . . . ?
C9A C8A C7A N1 17(7) . . . . ?
C9A C8A C7A C6A 162(4) . . . . ?
C7A N1 C11 C10A -3(4) . . . . ?
C7A C6A C1 Ir1 13(3) . . . . ?
C7A C6A C1 C2 -161(3) . . . . ?
F2A C5A C6A C1 -148(3) . . . . ?
F2A C5A C6A C7A 11(3) . . . . ?
F4A C14A C15A C16 -166(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
