# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_new
_database_code_depnum_ccdc_archive 'CCDC 1515629'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2017-08-17 downloaded from the CCDC.
;

_audit_creation_date             2016-11-09T11:23:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
(1,5-Cyclooctadiene)-bis(N,N'-dimethylthiourea)-iridium(IV)
;
_chemical_formula_sum            'C14 H26 Cl Ir N4 S2'
_chemical_formula_weight         542.16
_chemical_formula_moiety         'C14 H26 Ir N4 S2, Cl'

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

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

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

_cell_length_a                   10.697(4)
_cell_length_b                   15.165(6)
_cell_length_c                   14.304(4)
_cell_angle_alpha                90
_cell_angle_beta                 129.741(12)
_cell_angle_gamma                90
_cell_volume                     1784.2(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8896
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      28.52

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

_exptl_crystal_description       Cuboid
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.072
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_max          0.264
_exptl_crystal_density_diffrn    2.018
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_special_details           
;
The intensity data was collected on a Bruker X8 ApexII 4K Kappa CCD
diffractometer using an exposure time of 30 seconds/frame.  A total of 8896
frames were collected with a frame width of 0.5° covering up to θ = 28.00°
with 99.9% completeness accomplished.;
;

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

_exptl_absorpt_coefficient_mu    7.868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2352
_exptl_absorpt_correction_T_max  0.6100
_exptl_absorpt_process_details   
;
SADABS (Bruker, 2004)
;

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_number            32564
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         28.6
_diffrn_reflns_theta_full        28.6
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             4529
_reflns_number_gt                4153
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-92 (Sheldrick, 2008)'
_computing_molecular_graphics    'DIAMOND 3.0c (Brandenburg & Putz, 2004)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0146P)²+1.8683P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4529
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_ref         0.051
_refine_ls_wR_factor_gt          0.0494
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_restrained_S_all      1.06
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.104
_refine_diff_density_min         -1.224
_refine_diff_density_rms         0.129

#----------------------------------------------------------------------------#
#                   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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2726(4) -0.13356(19) 0.0524(3) 0.0206(6) Uani 1 1 d . . .
H1A H 0.3803 -0.1543 0.0844 0.031 Uiso 1 1 calc R . .
H1B H 0.2258 -0.0966 -0.0193 0.031 Uiso 1 1 calc R . .
H1C H 0.2016 -0.1844 0.0297 0.031 Uiso 1 1 calc R . .
C2 C 0.2649(4) -0.11555(18) 0.2168(3) 0.0180(6) Uani 1 1 d . . .
C3 C 0.1964(5) -0.2263(2) 0.3004(3) 0.0346(8) Uani 1 1 d . . .
H3A H 0.1504 -0.2859 0.2785 0.052 Uiso 0.5 1 calc PR . .
H3B H 0.1261 -0.1869 0.3031 0.052 Uiso 0.5 1 calc PR . .
H3C H 0.3051 -0.2276 0.3804 0.052 Uiso 0.5 1 calc PR . .
H3D H 0.2373 -0.181 0.3628 0.052 Uiso 0.5 1 calc PR . .
H3E H 0.2616 -0.28 0.3383 0.052 Uiso 0.5 1 calc PR . .
H3F H 0.0826 -0.2393 0.2609 0.052 Uiso 0.5 1 calc PR . .
C4 C 0.7260(4) -0.04405(18) 0.4539(3) 0.0213(6) Uani 1 1 d . . .
H4A H 0.7804 -0.0991 0.4622 0.032 Uiso 1 1 calc R . .
H4B H 0.6622 -0.0536 0.4803 0.032 Uiso 1 1 calc R . .
H4C H 0.8077 0.0018 0.5043 0.032 Uiso 1 1 calc R . .
C5 C 0.6651(4) -0.01160(18) 0.2633(2) 0.0164(5) Uani 1 1 d . . .
C6 C 0.8525(5) -0.0227(3) 0.2231(3) 0.0358(9) Uani 1 1 d . . .
H6A H 0.7575 -0.0224 0.1364 0.054 Uiso 1 1 calc R . .
H6B H 0.9295 -0.0679 0.2389 0.054 Uiso 1 1 calc R . .
H6C H 0.9051 0.0352 0.2467 0.054 Uiso 1 1 calc R . .
C13 C 0.3262(4) 0.1783(2) 0.3379(3) 0.0264(7) Uani 1 1 d . . .
H13A H 0.3431 0.2408 0.3631 0.032 Uiso 1 1 calc R . .
H13B H 0.3247 0.1435 0.3957 0.032 Uiso 1 1 calc R . .
C14 C 0.1608(4) 0.1694(2) 0.2111(3) 0.0268(7) Uani 1 1 d . . .
H14A H 0.0779 0.1565 0.2197 0.032 Uiso 1 1 calc R . .
H14B H 0.1324 0.2267 0.1686 0.032 Uiso 1 1 calc R . .
C17 C 0.2503(4) 0.1954(2) 0.0434(3) 0.0228(6) Uani 1 1 d . . .
H17A H 0.1583 0.237 -0.0071 0.027 Uiso 1 1 calc R . .
H17B H 0.2929 0.183 0.0003 0.027 Uiso 1 1 calc R . .
C18 C 0.3836(4) 0.23870(19) 0.1650(3) 0.0239(6) Uani 1 1 d . . .
H18A H 0.4514 0.2756 0.1557 0.029 Uiso 1 1 calc R . .
H18B H 0.3324 0.2782 0.1871 0.029 Uiso 1 1 calc R . .
N1 N 0.2876(3) -0.08251(15) 0.1446(2) 0.0168(5) Uani 1 1 d . . .
N2 N 0.2076(3) -0.19469(17) 0.2112(2) 0.0239(6) Uani 1 1 d . . .
N3 N 0.6192(3) -0.01637(16) 0.3278(2) 0.0173(5) Uani 1 1 d . . .
N4 N 0.8018(4) -0.04193(16) 0.2924(2) 0.0216(6) Uani 1 1 d . . .
H2 H 0.180(4) -0.228(2) 0.154(3) 0.028(10) Uiso 1 1 d . . .
H4 H 0.868(5) -0.069(3) 0.354(4) 0.033(11) Uiso 1 1 d . . .
C11 C 0.4923(4) 0.17446(18) 0.2675(3) 0.0207(6) Uani 1 1 d . . .
H11 H 0.6092 0.1778 0.3047 0.025 Uiso 1 1 calc R . .
C12 C 0.4678(4) 0.14822(18) 0.3469(3) 0.0210(6) Uani 1 1 d . . .
H12 H 0.5699 0.1367 0.4317 0.025 Uiso 1 1 calc R . .
C15 C 0.1530(4) 0.09828(19) 0.1328(3) 0.0205(6) Uani 1 1 d . . .
H15 H 0.0652 0.0538 0.1019 0.025 Uiso 1 1 calc R . .
C16 C 0.1892(3) 0.11058(19) 0.0568(3) 0.0184(6) Uani 1 1 d . . .
H16 H 0.1226 0.0737 -0.0185 0.022 Uiso 1 1 calc R . .
S1 S 0.32374(11) -0.03745(4) 0.32801(7) 0.02141(16) Uani 1 1 d . . .
S2 S 0.51215(10) 0.04022(5) 0.12559(7) 0.01885(15) Uani 1 1 d . . .
Ir1 Ir 0.391250(13) 0.039429(6) 0.219458(9) 0.01378(4) Uani 1 1 d . . .
Cl1 Cl 0.92370(10) 0.15584(5) 0.48151(8) 0.03181(18) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.447(3) . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 N1 1.303(4) . ?
C2 N2 1.326(4) . ?
C2 S1 1.746(3) . ?
C3 N2 1.439(4) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C3 H3D 0.98 . ?
C3 H3E 0.98 . ?
C3 H3F 0.98 . ?
C4 N3 1.449(4) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 N3 1.294(4) . ?
C5 N4 1.321(4) . ?
C5 S2 1.748(3) . ?
C6 N4 1.431(4) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C13 C12 1.506(4) . ?
C13 C14 1.528(5) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.518(4) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C17 C16 1.509(4) . ?
C17 C18 1.523(4) . ?
C17 H17A 0.99 . ?
C17 H17B 0.99 . ?
C18 C11 1.507(4) . ?
C18 H18A 0.99 . ?
C18 H18B 0.99 . ?
N1 Ir1 2.068(2) . ?
N2 H2 0.83(4) . ?
N3 Ir1 2.057(3) . ?
N4 H4 0.80(4) . ?
C11 C12 1.376(4) . ?
C11 Ir1 2.210(3) . ?
C11 H11 1 . ?
C12 Ir1 2.192(3) . ?
C12 H12 1 . ?
C15 C16 1.381(4) . ?
C15 Ir1 2.189(3) . ?
C15 H15 1 . ?
C16 Ir1 2.195(3) . ?
C16 H16 1 . ?
S1 Ir1 2.3928(9) . ?
S2 Ir1 2.3866(9) . ?

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 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 N2 127.8(3) . . ?
N1 C2 S1 108.6(2) . . ?
N2 C2 S1 123.6(2) . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C3 H3D 109.5 . . ?
H3A C3 H3D 141.1 . . ?
H3B C3 H3D 56.3 . . ?
H3C C3 H3D 56.3 . . ?
N2 C3 H3E 109.5 . . ?
H3A C3 H3E 56.3 . . ?
H3B C3 H3E 141.1 . . ?
H3C C3 H3E 56.3 . . ?
H3D C3 H3E 109.5 . . ?
N2 C3 H3F 109.5 . . ?
H3A C3 H3F 56.3 . . ?
H3B C3 H3F 56.3 . . ?
H3C C3 H3F 141.1 . . ?
H3D C3 H3F 109.5 . . ?
H3E C3 H3F 109.5 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 N4 127.1(3) . . ?
N3 C5 S2 108.7(2) . . ?
N4 C5 S2 124.2(2) . . ?
N4 C6 H6A 109.5 . . ?
N4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C13 C14 114.4(2) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 114.4(3) . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C13 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C17 C18 112.8(2) . . ?
C16 C17 H17A 109 . . ?
C18 C17 H17A 109 . . ?
C16 C17 H17B 109 . . ?
C18 C17 H17B 109 . . ?
H17A C17 H17B 107.8 . . ?
C11 C18 C17 114.1(2) . . ?
C11 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C11 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C2 N1 C1 123.3(2) . . ?
C2 N1 Ir1 104.08(18) . . ?
C1 N1 Ir1 131.33(19) . . ?
C2 N2 C3 123.0(3) . . ?
C2 N2 H2 118(2) . . ?
C3 N2 H2 119(2) . . ?
C5 N3 C4 123.1(3) . . ?
C5 N3 Ir1 104.29(19) . . ?
C4 N3 Ir1 132.0(2) . . ?
C5 N4 C6 123.0(3) . . ?
C5 N4 H4 123(3) . . ?
C6 N4 H4 113(3) . . ?
C12 C11 C18 123.7(3) . . ?
C12 C11 Ir1 71.09(16) . . ?
C18 C11 Ir1 112.13(19) . . ?
C12 C11 H11 114.1 . . ?
C18 C11 H11 114.1 . . ?
Ir1 C11 H11 114.1 . . ?
C11 C12 C13 123.5(3) . . ?
C11 C12 Ir1 72.47(16) . . ?
C13 C12 Ir1 109.6(2) . . ?
C11 C12 H12 114.5 . . ?
C13 C12 H12 114.5 . . ?
Ir1 C12 H12 114.5 . . ?
C16 C15 C14 125.0(3) . . ?
C16 C15 Ir1 71.90(17) . . ?
C14 C15 Ir1 112.1(2) . . ?
C16 C15 H15 113.5 . . ?
C14 C15 H15 113.5 . . ?
Ir1 C15 H15 113.5 . . ?
C15 C16 C17 125.3(3) . . ?
C15 C16 Ir1 71.39(17) . . ?
C17 C16 Ir1 109.92(19) . . ?
C15 C16 H16 114.1 . . ?
C17 C16 H16 114.1 . . ?
Ir1 C16 H16 114.1 . . ?
C2 S1 Ir1 79.76(10) . . ?
C5 S2 Ir1 79.44(10) . . ?
N3 Ir1 N1 90.42(10) . . ?
N3 Ir1 C15 169.99(10) . . ?
N1 Ir1 C15 91.52(11) . . ?
N3 Ir1 C12 92.88(11) . . ?
N1 Ir1 C12 153.50(10) . . ?
C15 Ir1 C12 81.08(12) . . ?
N3 Ir1 C16 152.90(10) . . ?
N1 Ir1 C16 92.99(10) . . ?
C15 Ir1 C16 36.71(11) . . ?
C12 Ir1 C16 95.90(11) . . ?
N3 Ir1 C11 92.20(11) . . ?
N1 Ir1 C11 169.50(10) . . ?
C15 Ir1 C11 87.66(12) . . ?
C12 Ir1 C11 36.44(11) . . ?
C16 Ir1 C11 80.13(11) . . ?
N3 Ir1 S2 67.56(7) . . ?
N1 Ir1 S2 90.99(7) . . ?
C15 Ir1 S2 122.21(8) . . ?
C12 Ir1 S2 114.53(9) . . ?
C16 Ir1 S2 85.50(8) . . ?
C11 Ir1 S2 80.64(8) . . ?
N3 Ir1 S1 90.85(7) . . ?
N1 Ir1 S1 67.42(7) . . ?
C15 Ir1 S1 80.85(8) . . ?
C12 Ir1 S1 86.24(8) . . ?
C16 Ir1 S1 115.23(8) . . ?
C11 Ir1 S1 122.68(8) . . ?
S2 Ir1 S1 149.82(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 C13 C14 C15 26.1(4) . . . . ?
C16 C17 C18 C11 33.0(4) . . . . ?
N2 C2 N1 C1 -8.5(5) . . . . ?
S1 C2 N1 C1 171.2(2) . . . . ?
N2 C2 N1 Ir1 -176.8(3) . . . . ?
S1 C2 N1 Ir1 3.0(2) . . . . ?
N1 C2 N2 C3 176.3(3) . . . . ?
S1 C2 N2 C3 -3.5(5) . . . . ?
N4 C5 N3 C4 10.6(4) . . . . ?
S2 C5 N3 C4 -170.9(2) . . . . ?
N4 C5 N3 Ir1 -177.4(3) . . . . ?
S2 C5 N3 Ir1 1.1(2) . . . . ?
N3 C5 N4 C6 -170.9(3) . . . . ?
S2 C5 N4 C6 10.8(4) . . . . ?
C17 C18 C11 C12 -94.4(3) . . . . ?
C17 C18 C11 Ir1 -13.0(3) . . . . ?
C18 C11 C12 C13 2.2(4) . . . . ?
Ir1 C11 C12 C13 -102.3(3) . . . . ?
C18 C11 C12 Ir1 104.5(3) . . . . ?
C14 C13 C12 C11 49.3(4) . . . . ?
C14 C13 C12 Ir1 -32.3(3) . . . . ?
C13 C14 C15 C16 -89.2(4) . . . . ?
C13 C14 C15 Ir1 -6.4(3) . . . . ?
C14 C15 C16 C17 3.1(5) . . . . ?
Ir1 C15 C16 C17 -101.7(3) . . . . ?
C14 C15 C16 Ir1 104.8(3) . . . . ?
C18 C17 C16 C15 44.6(4) . . . . ?
C18 C17 C16 Ir1 -36.3(3) . . . . ?
N1 C2 S1 Ir1 -2.54(19) . . . . ?
N2 C2 S1 Ir1 177.3(3) . . . . ?
N3 C5 S2 Ir1 -0.94(18) . . . . ?
N4 C5 S2 Ir1 177.6(3) . . . . ?
C5 N3 Ir1 N1 90.07(19) . . . . ?
C4 N3 Ir1 N1 -98.9(3) . . . . ?
C5 N3 Ir1 C15 -168.8(5) . . . . ?
C4 N3 Ir1 C15 2.2(7) . . . . ?
C5 N3 Ir1 C12 -116.23(19) . . . . ?
C4 N3 Ir1 C12 54.8(3) . . . . ?
C5 N3 Ir1 C16 -7.3(3) . . . . ?
C4 N3 Ir1 C16 163.7(2) . . . . ?
C5 N3 Ir1 C11 -79.77(19) . . . . ?
C4 N3 Ir1 C11 91.2(3) . . . . ?
C5 N3 Ir1 S2 -0.83(16) . . . . ?
C4 N3 Ir1 S2 170.2(3) . . . . ?
C5 N3 Ir1 S1 157.49(18) . . . . ?
C4 N3 Ir1 S1 -31.5(2) . . . . ?
C2 N1 Ir1 N3 88.5(2) . . . . ?
C1 N1 Ir1 N3 -78.4(3) . . . . ?
C2 N1 Ir1 C15 -81.7(2) . . . . ?
C1 N1 Ir1 C15 111.4(3) . . . . ?
C2 N1 Ir1 C12 -8.8(4) . . . . ?
C1 N1 Ir1 C12 -175.7(3) . . . . ?
C2 N1 Ir1 C16 -118.4(2) . . . . ?
C1 N1 Ir1 C16 74.7(3) . . . . ?
C2 N1 Ir1 C11 -167.0(5) . . . . ?
C1 N1 Ir1 C11 26.1(7) . . . . ?
C2 N1 Ir1 S2 156.08(19) . . . . ?
C1 N1 Ir1 S2 -10.8(3) . . . . ?
C2 N1 Ir1 S1 -2.23(17) . . . . ?
C1 N1 Ir1 S1 -169.1(3) . . . . ?
C16 C15 Ir1 N3 166.0(5) . . . . ?
C14 C15 Ir1 N3 44.7(7) . . . . ?
C16 C15 Ir1 N1 -92.96(18) . . . . ?
C14 C15 Ir1 N1 145.8(2) . . . . ?
C16 C15 Ir1 C12 112.61(19) . . . . ?
C14 C15 Ir1 C12 -8.6(2) . . . . ?
C14 C15 Ir1 C16 -121.2(3) . . . . ?
C16 C15 Ir1 C11 76.58(18) . . . . ?
C14 C15 Ir1 C11 -44.7(2) . . . . ?
C16 C15 Ir1 S2 -0.8(2) . . . . ?
C14 C15 Ir1 S2 -122.07(19) . . . . ?
C16 C15 Ir1 S1 -159.79(17) . . . . ?
C14 C15 Ir1 S1 79.0(2) . . . . ?
C11 C12 Ir1 N3 89.80(19) . . . . ?
C13 C12 Ir1 N3 -150.0(2) . . . . ?
C11 C12 Ir1 N1 -173.5(2) . . . . ?
C13 C12 Ir1 N1 -53.3(3) . . . . ?
C11 C12 Ir1 C15 -98.22(19) . . . . ?
C13 C12 Ir1 C15 21.9(2) . . . . ?
C11 C12 Ir1 C16 -64.5(2) . . . . ?
C13 C12 Ir1 C16 55.6(2) . . . . ?
C13 C12 Ir1 C11 120.2(3) . . . . ?
C11 C12 Ir1 S2 23.2(2) . . . . ?
C13 C12 Ir1 S2 143.37(18) . . . . ?
C11 C12 Ir1 S1 -179.53(18) . . . . ?
C13 C12 Ir1 S1 -59.4(2) . . . . ?
C15 C16 Ir1 N3 -174.7(2) . . . . ?
C17 C16 Ir1 N3 -52.9(3) . . . . ?
C15 C16 Ir1 N1 88.54(18) . . . . ?
C17 C16 Ir1 N1 -149.7(2) . . . . ?
C17 C16 Ir1 C15 121.8(3) . . . . ?
C15 C16 Ir1 C12 -66.46(19) . . . . ?
C17 C16 Ir1 C12 55.3(2) . . . . ?
C15 C16 Ir1 C11 -99.44(19) . . . . ?
C17 C16 Ir1 C11 22.3(2) . . . . ?
C15 C16 Ir1 S2 179.30(17) . . . . ?
C17 C16 Ir1 S2 -58.93(19) . . . . ?
C15 C16 Ir1 S1 22.15(19) . . . . ?
C17 C16 Ir1 S1 143.92(17) . . . . ?
C12 C11 Ir1 N3 -91.87(19) . . . . ?
C18 C11 Ir1 N3 148.6(2) . . . . ?
C12 C11 Ir1 N1 163.8(5) . . . . ?
C18 C11 Ir1 N1 44.3(7) . . . . ?
C12 C11 Ir1 C15 78.12(19) . . . . ?
C18 C11 Ir1 C15 -41.4(2) . . . . ?
C18 C11 Ir1 C12 -119.5(3) . . . . ?
C12 C11 Ir1 C16 114.3(2) . . . . ?
C18 C11 Ir1 C16 -5.3(2) . . . . ?
C12 C11 Ir1 S2 -158.70(19) . . . . ?
C18 C11 Ir1 S2 81.8(2) . . . . ?
C12 C11 Ir1 S1 0.6(2) . . . . ?
C18 C11 Ir1 S1 -119.0(2) . . . . ?
C5 S2 Ir1 N3 0.61(12) . . . . ?
C5 S2 Ir1 N1 -89.43(12) . . . . ?
C5 S2 Ir1 C15 178.15(13) . . . . ?
C5 S2 Ir1 C12 83.21(13) . . . . ?
C5 S2 Ir1 C16 177.65(12) . . . . ?
C5 S2 Ir1 C11 96.93(13) . . . . ?
C5 S2 Ir1 S1 -46.69(11) . . . . ?
C2 S1 Ir1 N3 -88.46(12) . . . . ?
C2 S1 Ir1 N1 1.64(12) . . . . ?
C2 S1 Ir1 C15 97.16(13) . . . . ?
C2 S1 Ir1 C12 178.71(13) . . . . ?
C2 S1 Ir1 C16 83.96(13) . . . . ?
C2 S1 Ir1 C11 178.38(14) . . . . ?
C2 S1 Ir1 S2 -45.67(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1C N2 0.98 2.56 2.919(4) 101.6 .
C3 H3D S1 0.98 2.54 3.086(4) 115.4 .
C4 H4B S1 0.98 2.8 3.444(4) 124.1 .
C6 H6A S2 0.98 2.7 3.101(4) 104.9 .
C17 H17B S2 0.99 2.83 3.248(3) 106 .
C11 H11 Cl1 1 2.64 3.562(4) 154.1 .
N2 H2 Cl1 0.83(4) 2.32(4) 3.124(3) 164(3) 2_645
C1 H1C Cl1 0.98 2.72 3.680(3) 165.2 2_645
N4 H4 Cl1 0.80(4) 2.36(4) 3.150(3) 172(4) 3_756
C14 H14B Cl1 0.99 2.77 3.686(4) 154 4_465

# The following lines are used to test the character set of files sent by
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# END of CIF
