# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_str2042
_database_code_depnum_ccdc_archive 'CCDC 1850450'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;
_audit_creation_date             2018-01-15
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H23 Ir N2 O4 S, 3(C H Cl3)'
_chemical_formula_sum            'C18 H26 Cl9 Ir N2 O4 S'
_chemical_formula_weight         877.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H23 N2 O4 S Ir Cl'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2915(4)
_cell_length_b                   16.6242(6)
_cell_length_c                   32.7927(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6155.6(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12166
_cell_measurement_temperature    199.9(4)
_cell_measurement_theta_max      29.3840
_cell_measurement_theta_min      2.4810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.215
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.424
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 46 0.0812
0 1 -46 0.0812
6 -22 -4 0.1459
-5 18 26 0.1873
14 4 19 0.0703
-14 7 -14 0.1233
-11 -13 -19 0.1321
-4 -22 -13 0.1452
4 22 13 0.1452
-7 3 41 0.1205
-6 -5 42 0.1044
6 4 -42 0.0944

_exptl_crystal_size_max          0.353
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.162
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0093 -1.0003 45.9349 -0.0150 -0.9945 0.0029
0.0093 1.0003 -45.9349 0.0150 0.9945 -0.0029
5.9813 -21.9714 -3.9919 -0.0216 0.0491 1.0121
-4.9889 17.9758 25.9612 0.0082 -0.5306 -0.8483
13.9797 3.9865 18.9982 -0.8944 -0.3890 0.1336
-13.9749 6.9975 -14.0014 0.7270 0.3026 -0.5760
-10.9884 -12.9751 -18.9963 0.8524 0.3743 0.2911
-4.0036 -21.9660 -12.9961 0.5717 0.2339 0.7991
4.0036 21.9660 12.9961 -0.5717 -0.2339 -0.7991
-6.9969 2.9977 40.9315 0.3397 -0.8854 -0.3067
-6.0026 -4.9914 41.9290 0.3997 -0.9216 0.0334
6.0020 3.9928 -41.9294 -0.3848 0.9196 0.0065

_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            32939
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.9(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  84.00   0.50    5.00    --   10.93  57.00 -30.00  202
  2  ω    -73.00  39.00   0.50    5.00    --   10.93   0.00 150.00  224
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0588232000
_diffrn_orient_matrix_UB_12      -0.0149112000
_diffrn_orient_matrix_UB_13      -0.0006629000
_diffrn_orient_matrix_UB_21      0.0009775000
_diffrn_orient_matrix_UB_22      0.0019567000
_diffrn_orient_matrix_UB_23      -0.0216070000
_diffrn_orient_matrix_UB_31      0.0220332000
_diffrn_orient_matrix_UB_32      -0.0399202000
_diffrn_orient_matrix_UB_33      -0.0008021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5530
_reflns_number_total             6277
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.757
_refine_diff_density_min         -1.256
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         6277
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+23.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C32(H32), C28(H28)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C21(H21A,H21B,
 H21C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C)
;
_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
Ir1 Ir 0.36509(2) 0.46514(2) 0.62255(2) 0.02438(7) Uani 1 1 d . . . . .
O4 O 0.3397(3) 0.5929(2) 0.61878(11) 0.0344(8) Uani 1 1 d . . . . .
Cl29 Cl 0.1651(3) 0.50424(16) 0.35299(17) 0.1776(19) Uani 1 1 d . . . . .
S5 S 0.46467(10) 0.61348(7) 0.60547(3) 0.0272(2) Uani 1 1 d . . . . .
Cl35 Cl 0.49244(14) 0.83810(10) 0.51733(6) 0.0635(4) Uani 1 1 d . . . . .
Cl26 Cl 0.88381(18) 0.32946(11) 0.71234(7) 0.0759(5) Uani 1 1 d . . . . .
Cl25 Cl 0.90649(17) 0.18831(13) 0.76159(6) 0.0749(5) Uani 1 1 d . . . . .
Cl34 Cl 0.72696(16) 0.77939(11) 0.50072(7) 0.0746(5) Uani 1 1 d . . . . .
Cl27 Cl 1.11368(15) 0.25938(14) 0.72703(5) 0.0703(5) Uani 1 1 d . . . . .
Cl31 Cl 0.1639(2) 0.3692(2) 0.40627(7) 0.1168(10) Uani 1 1 d . . . . .
O3 O 0.5214(3) 0.53038(18) 0.60401(11) 0.0317(7) Uani 1 1 d . . . . .
Cl33 Cl 0.6722(2) 0.84980(18) 0.57826(7) 0.1011(8) Uani 1 1 d . . . . .
Cl30 Cl 0.1791(3) 0.34775(19) 0.32069(7) 0.1215(10) Uani 1 1 d . . . . .
C2 C 0.3233(4) 0.4618(3) 0.56205(14) 0.0266(9) Uani 1 1 d . . . . .
O7 O 0.4644(3) 0.6493(2) 0.56552(11) 0.0439(9) Uani 1 1 d . . . . .
N8 N 0.2248(4) 0.4926(2) 0.54403(12) 0.0318(9) Uani 1 1 d . . . . .
N12 N 0.3878(4) 0.4310(2) 0.53113(12) 0.0305(9) Uani 1 1 d . . . . .
O6 O 0.5244(4) 0.6623(2) 0.63546(12) 0.0485(10) Uani 1 1 d . . . . .
C9 C 0.1288(5) 0.5330(3) 0.56498(19) 0.0462(14) Uani 1 1 d . . . . .
H9A H 0.1421 0.5308 0.5939 0.069 Uiso 1 1 calc GR . . . .
H9B H 0.0553 0.5068 0.5586 0.069 Uiso 1 1 calc GR . . . .
H9C H 0.1253 0.5881 0.5564 0.069 Uiso 1 1 calc GR . . . .
C11 C 0.3305(5) 0.4424(3) 0.49435(15) 0.0408(12) Uani 1 1 d . . . . .
H11 H 0.3575 0.4264 0.4688 0.049 Uiso 1 1 calc R . . . .
C20 C 0.3749(7) 0.4450(4) 0.68809(17) 0.0544(18) Uani 1 1 d . . . . .
C13 C 0.5004(5) 0.3896(3) 0.53536(16) 0.0391(12) Uani 1 1 d . . . . .
H13A H 0.5433 0.4120 0.5579 0.059 Uiso 1 1 calc GR . . . .
H13B H 0.5457 0.3962 0.5108 0.059 Uiso 1 1 calc GR . . . .
H13C H 0.4865 0.3334 0.5401 0.059 Uiso 1 1 calc GR . . . .
C10 C 0.2293(5) 0.4806(3) 0.50230(15) 0.0405(12) Uani 1 1 d . . . . .
H10 H 0.1725 0.4963 0.4834 0.049 Uiso 1 1 calc R . . . .
C24 C 0.9633(5) 0.2404(3) 0.71954(16) 0.0433(12) Uani 1 1 d . . . . .
H24 H 0.9541 0.2067 0.6952 0.052 Uiso 1 1 calc R . . . .
C32 C 0.6178(5) 0.7906(4) 0.5381(2) 0.0532(15) Uani 1 1 d . . . . .
H32 H 0.5954 0.7376 0.5486 0.064 Uiso 1 1 calc R . . . .
C28 C 0.2183(5) 0.4079(4) 0.3612(2) 0.0547(16) Uani 1 1 d . . . . .
H28 H 0.3049 0.4100 0.3629 0.066 Uiso 1 1 calc R . . . .
C22 C 0.2558(6) 0.4385(3) 0.67420(17) 0.0478(14) Uani 1 1 d . . . . .
C14 C 0.2484(6) 0.3747(3) 0.64552(16) 0.0457(14) Uani 1 1 d . . . . .
C18 C 0.4400(6) 0.3860(4) 0.6678(2) 0.0611(19) Uani 1 1 d . . . . .
C16 C 0.3633(7) 0.3425(3) 0.64144(19) 0.0562(18) Uani 1 1 d . . . . .
C23 C 0.1565(9) 0.4914(6) 0.6875(3) 0.117(4) Uani 1 1 d . . . . .
H23A H 0.1810 0.5466 0.6861 0.175 Uiso 1 1 calc GR . . . .
H23B H 0.1350 0.4784 0.7151 0.175 Uiso 1 1 calc GR . . . .
H23C H 0.0895 0.4833 0.6700 0.175 Uiso 1 1 calc GR . . . .
C21 C 0.4173(12) 0.5068(6) 0.7186(2) 0.139(6) Uani 1 1 d . . . . .
H21A H 0.5020 0.5109 0.7172 0.209 Uiso 1 1 calc GR . . . .
H21B H 0.3942 0.4907 0.7455 0.209 Uiso 1 1 calc GR . . . .
H21C H 0.3827 0.5581 0.7123 0.209 Uiso 1 1 calc GR . . . .
C15 C 0.1375(8) 0.3445(6) 0.6254(3) 0.107(4) Uani 1 1 d . . . . .
H15A H 0.0806 0.3874 0.6238 0.160 Uiso 1 1 calc GR . . . .
H15B H 0.1051 0.3010 0.6411 0.160 Uiso 1 1 calc GR . . . .
H15C H 0.1557 0.3259 0.5984 0.160 Uiso 1 1 calc GR . . . .
C17 C 0.3930(13) 0.2670(5) 0.6177(3) 0.142(6) Uani 1 1 d . . . . .
H17A H 0.3508 0.2672 0.5923 0.213 Uiso 1 1 calc GR . . . .
H17B H 0.3705 0.2206 0.6333 0.213 Uiso 1 1 calc GR . . . .
H17C H 0.4766 0.2654 0.6125 0.213 Uiso 1 1 calc GR . . . .
C19 C 0.5714(7) 0.3736(7) 0.6718(4) 0.147(6) Uani 1 1 d . . . . .
H19A H 0.6013 0.3486 0.6476 0.220 Uiso 1 1 calc GR . . . .
H19B H 0.5873 0.3397 0.6949 0.220 Uiso 1 1 calc GR . . . .
H19C H 0.6096 0.4247 0.6756 0.220 Uiso 1 1 calc GR . . . .


_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 O4 2.148(3) . ?
Ir1 S5 2.7674(11) . ?
Ir1 O3 2.159(3) . ?
Ir1 C2 2.040(5) . ?
Ir1 C20 2.178(5) . ?
Ir1 C22 2.142(5) . ?
Ir1 C14 2.137(5) . ?
Ir1 C18 2.157(6) . ?
Ir1 C16 2.132(5) . ?
O4 S5 1.516(3) . ?
Cl29 C28 1.732(7) . ?
S5 O3 1.524(3) . ?
S5 O7 1.439(4) . ?
S5 O6 1.443(4) . ?
Cl35 C32 1.758(6) . ?
Cl26 C24 1.747(6) . ?
Cl25 C24 1.750(6) . ?
Cl34 C32 1.748(7) . ?
Cl27 C24 1.745(6) . ?
Cl31 C28 1.725(7) . ?
Cl33 C32 1.755(7) . ?
Cl30 C28 1.721(6) . ?
C2 N8 1.359(6) . ?
C2 N12 1.350(6) . ?
N8 C9 1.448(7) . ?
N8 C10 1.384(6) . ?
N12 C11 1.382(6) . ?
N12 C13 1.452(6) . ?
C11 C10 1.334(8) . ?
C20 C22 1.424(9) . ?
C20 C18 1.394(10) . ?
C20 C21 1.512(9) . ?
C22 C14 1.420(8) . ?
C22 C23 1.490(10) . ?
C14 C16 1.410(9) . ?
C14 C15 1.502(9) . ?
C18 C16 1.423(10) . ?
C18 C19 1.504(10) . ?
C16 C17 1.513(10) . ?

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
O4 Ir1 S5 32.97(9) . . ?
O4 Ir1 O3 66.18(12) . . ?
O4 Ir1 C20 102.4(2) . . ?
O4 Ir1 C18 134.1(2) . . ?
O3 Ir1 S5 33.20(8) . . ?
O3 Ir1 C20 108.26(19) . . ?
C2 Ir1 O4 86.54(15) . . ?
C2 Ir1 S5 85.48(12) . . ?
C2 Ir1 O3 85.92(16) . . ?
C2 Ir1 C20 165.3(2) . . ?
C2 Ir1 C22 129.1(2) . . ?
C2 Ir1 C14 100.44(19) . . ?
C2 Ir1 C18 138.1(3) . . ?
C2 Ir1 C16 104.8(2) . . ?
C20 Ir1 S5 108.41(15) . . ?
C22 Ir1 O4 99.96(18) . . ?
C22 Ir1 S5 125.33(16) . . ?
C22 Ir1 O3 142.9(2) . . ?
C22 Ir1 C20 38.5(2) . . ?
C22 Ir1 C18 63.6(3) . . ?
C14 Ir1 O4 129.4(2) . . ?
C14 Ir1 S5 161.63(18) . . ?
C14 Ir1 O3 163.1(2) . . ?
C14 Ir1 C20 64.9(2) . . ?
C14 Ir1 C22 38.8(2) . . ?
C14 Ir1 C18 64.5(2) . . ?
C18 Ir1 S5 121.56(19) . . ?
C18 Ir1 O3 100.34(19) . . ?
C18 Ir1 C20 37.5(3) . . ?
C16 Ir1 O4 164.17(19) . . ?
C16 Ir1 S5 156.2(2) . . ?
C16 Ir1 O3 124.8(2) . . ?
C16 Ir1 C20 64.3(2) . . ?
C16 Ir1 C22 64.3(2) . . ?
C16 Ir1 C14 38.6(2) . . ?
C16 Ir1 C18 38.8(3) . . ?
S5 O4 Ir1 96.60(17) . . ?
O4 S5 Ir1 50.43(13) . . ?
O4 S5 O3 101.33(19) . . ?
O3 S5 Ir1 50.90(12) . . ?
O7 S5 Ir1 123.50(16) . . ?
O7 S5 O4 110.7(2) . . ?
O7 S5 O3 110.3(2) . . ?
O7 S5 O6 112.9(2) . . ?
O6 S5 Ir1 123.63(18) . . ?
O6 S5 O4 111.4(2) . . ?
O6 S5 O3 109.6(2) . . ?
S5 O3 Ir1 95.90(16) . . ?
N8 C2 Ir1 127.0(3) . . ?
N12 C2 Ir1 128.0(3) . . ?
N12 C2 N8 105.0(4) . . ?
C2 N8 C9 125.5(4) . . ?
C2 N8 C10 110.2(4) . . ?
C10 N8 C9 124.3(4) . . ?
C2 N12 C11 110.5(4) . . ?
C2 N12 C13 125.5(4) . . ?
C11 N12 C13 123.9(4) . . ?
C10 C11 N12 107.2(4) . . ?
C22 C20 Ir1 69.4(3) . . ?
C22 C20 C21 124.2(8) . . ?
C18 C20 Ir1 70.4(3) . . ?
C18 C20 C22 107.0(5) . . ?
C18 C20 C21 128.8(8) . . ?
C21 C20 Ir1 124.4(4) . . ?
C11 C10 N8 107.1(5) . . ?
Cl26 C24 Cl25 109.7(3) . . ?
Cl27 C24 Cl26 111.4(3) . . ?
Cl27 C24 Cl25 109.6(3) . . ?
Cl34 C32 Cl35 110.1(4) . . ?
Cl34 C32 Cl33 109.9(3) . . ?
Cl33 C32 Cl35 108.7(4) . . ?
Cl31 C28 Cl29 110.8(4) . . ?
Cl30 C28 Cl29 109.1(4) . . ?
Cl30 C28 Cl31 110.7(4) . . ?
C20 C22 Ir1 72.1(3) . . ?
C20 C22 C23 124.9(7) . . ?
C14 C22 Ir1 70.4(3) . . ?
C14 C22 C20 108.9(6) . . ?
C14 C22 C23 126.2(8) . . ?
C23 C22 Ir1 122.9(5) . . ?
C22 C14 Ir1 70.8(3) . . ?
C22 C14 C15 126.1(7) . . ?
C16 C14 Ir1 70.5(3) . . ?
C16 C14 C22 107.0(5) . . ?
C16 C14 C15 126.8(7) . . ?
C15 C14 Ir1 126.5(4) . . ?
C20 C18 Ir1 72.1(3) . . ?
C20 C18 C16 109.1(6) . . ?
C20 C18 C19 125.1(9) . . ?
C16 C18 Ir1 69.7(3) . . ?
C16 C18 C19 125.8(9) . . ?
C19 C18 Ir1 122.0(5) . . ?
C14 C16 Ir1 70.9(3) . . ?
C14 C16 C18 108.0(5) . . ?
C14 C16 C17 124.6(8) . . ?
C18 C16 Ir1 71.6(3) . . ?
C18 C16 C17 126.8(8) . . ?
C17 C16 Ir1 129.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.292
_oxdiff_exptl_absorpt_empirical_full_min 0.796
####################################################################### 
# 
# 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_mp-325
_database_code_depnum_ccdc_archive 'CCDC 1850452'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;
_audit_creation_date             2018-06-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H27 Ir N2 O2'
_chemical_formula_sum            'C22 H27 Ir N2 O2'
_chemical_formula_weight         543.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H28IrN2O2
_chemical_oxdiff_usercomment     'CH2Cl2 hexano'
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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5920(2)
_cell_length_b                   10.2464(3)
_cell_length_c                   12.6648(3)
_cell_angle_alpha                78.655(2)
_cell_angle_beta                 82.445(2)
_cell_angle_gamma                67.017(3)
_cell_volume                     1004.57(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1100
_cell_measurement_theta_min      2.9590
_shelx_estimated_absorpt_T_max   0.618
_shelx_estimated_absorpt_T_min   0.502
_exptl_absorpt_coefficient_mu    6.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             532
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1091
_diffrn_reflns_av_unetI/netI     0.0757
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.684
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0655
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -49.00  52.00   1.00   12.50    --  -18.55  77.00-150.00  101
  2  ω    -49.00  52.00   1.00   12.50    --  -18.55  77.00  90.00  101
  3  ω     -9.00  91.00   1.00   12.50    --   20.66  77.00  90.00  100
  4  ω     -9.00  91.00   1.00   12.50    --   20.66  77.00-180.00  100
  5  ω     -9.00  91.00   1.00   12.50    --   20.66  77.00 -30.00  100
  6  ω    -95.00 -66.00   1.00   12.50    --  -18.55-179.00  60.00   29
  7  ω     -1.00  89.00   1.00   12.50    --   20.66  57.00 -90.00   90
  8  ω    -25.00  63.00   1.00   12.50    --   20.66 -99.00 -30.00   88
  9  ω    -25.00  63.00   1.00   12.50    --   20.66 -99.00  60.00   88
 10  ω     34.00  97.00   1.00   12.50    --   20.66 179.00  60.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0862885000
_diffrn_orient_matrix_UB_12      -0.0160216000
_diffrn_orient_matrix_UB_13      0.0075320000
_diffrn_orient_matrix_UB_21      0.0199284000
_diffrn_orient_matrix_UB_22      -0.0030977000
_diffrn_orient_matrix_UB_23      -0.0558344000
_diffrn_orient_matrix_UB_31      -0.0150872000
_diffrn_orient_matrix_UB_32      0.0743967000
_diffrn_orient_matrix_UB_33      -0.0100360000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4030
_reflns_number_total             4599
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.750
_refine_diff_density_min         -3.666
_refine_diff_density_rms         0.251
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4599
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.149
_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)+(0.0463P)²+0.4322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.1087
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C21-C26 \\sim C27-C20
 with sigma of 0.02
 C21-C23 \\sim C27-C22
 with sigma of 0.02
 C21-C29 \\sim C27-C28
 with sigma of 0.02
 C24-C25 \\sim C18-C19
 with sigma of 0.02
 C24-C23 \\sim C18-C22
 with sigma of 0.02
 C24-C33 \\sim C18-C32
 with sigma of 0.02
 C25-C26 \\sim C19-C20
 with sigma of 0.02
 C25-C35 \\sim C19-C34
 with sigma of 0.02
 C26-C3 \\sim C20-C36
 with sigma of 0.02
 C23-C31 \\sim C22-C30
 with sigma of 0.02
 Ir1-C21 \\sim Ir1-C27
 with sigma of 0.04
 Ir1-C24 \\sim Ir1-C18
 with sigma of 0.04
 Ir1-C25 \\sim Ir1-C19
 with sigma of 0.04
 Ir1-C26 \\sim Ir1-C20
 with sigma of 0.04
 Ir1-C23 \\sim Ir1-C22
 with sigma of 0.04
 Ir1-C35 \\sim Ir1-C34
 with sigma of 0.04
 Ir1-C3 \\sim Ir1-C36
 with sigma of 0.04
 Ir1-C29 \\sim Ir1-C28
 with sigma of 0.04
 Ir1-C33 \\sim Ir1-C32
 with sigma of 0.04
 Ir1-C31 \\sim Ir1-C30
 with sigma of 0.04
 C21-C24 \\sim C27-C18
 with sigma of 0.04
 C21-C25 \\sim C27-C19
 with sigma of 0.04
 C21-C3 \\sim C27-C36
 with sigma of 0.04
 C21-C31 \\sim C27-C30
 with sigma of 0.04
 C24-C26 \\sim C18-C20
 with sigma of 0.04
 C24-C35 \\sim C18-C34
 with sigma of 0.04
 C24-C31 \\sim C18-C30
 with sigma of 0.04
 C25-C23 \\sim C19-C22
 with sigma of 0.04
 C25-C3 \\sim C19-C36
 with sigma of 0.04
 C25-C33 \\sim C19-C32
 with sigma of 0.04
 C26-C23 \\sim C20-C22
 with sigma of 0.04
 C26-C35 \\sim C20-C34
 with sigma of 0.04
 C26-C29 \\sim C20-C28
 with sigma of 0.04
 C23-C29 \\sim C22-C28
 with sigma of 0.04
 C23-C33 \\sim C22-C32
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C19) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(C36)=Sof(H36A)=Sof(H36B)=Sof(H36C)=Sof(C20)=Sof(C27)=Sof(C28)=Sof(H28A)=
 Sof(H28B)=Sof(H28C)=Sof(C22)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C32)=
 Sof(H32A)=Sof(H32B)=Sof(H32C)=Sof(C18)=Sof(C19)=Sof(C34)=Sof(H34A)=Sof(H34B)=
 Sof(H34C)=1-FVAR(1)
 Sof(C21)=Sof(C24)=Sof(C25)=Sof(C26)=Sof(C23)=Sof(C35)=Sof(H35A)=Sof(H35B)=
 Sof(H35C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C29)=Sof(H29A)=Sof(H29B)=
 Sof(H29C)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C31)=Sof(H31A)=Sof(H31B)=
 Sof(H31C)=FVAR(1)
5.a Me refined with riding coordinates:
 C31(H31A,H31B,H31C)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C8(H8), C14(H14), C9(H9), C11(H11), C10(H10)
5.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C35(H35A,H35B,H35C), C3(H3A,H3B,
 H3C), C29(H29A,H29B,H29C), C33(H33A,H33B,H33C), C36(H36A,H36B,H36C), C28(H28A,
 H28B,H28C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C34(H34A,H34B,H34C)
;
_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
Ir1 Ir 0.18395(3) 0.15573(2) 0.19904(2) 0.03368(11) Uani 1 1 d D . . . .
O3 O 0.2391(6) -0.0580(4) 0.1851(3) 0.0351(10) Uani 1 1 d . . . . .
N16 N -0.0215(7) 0.1955(6) 0.4157(4) 0.0339(12) Uani 1 1 d . . . . .
C15 C -0.1631(9) 0.1806(7) 0.4711(5) 0.0370(15) Uani 1 1 d . . . . .
H15 H -0.2111 0.2122 0.5362 0.044 Uiso 1 1 calc R . . . .
N13 N -0.1093(7) 0.0882(6) 0.3233(4) 0.0310(11) Uani 1 1 d . . . . .
C6 C 0.4278(8) -0.0984(6) 0.3185(5) 0.0298(13) Uani 1 1 d . . . . .
C2 C 0.0129(8) 0.1391(6) 0.3231(4) 0.0303(13) Uani 1 1 d . . . . .
C4 C 0.3733(8) 0.0569(7) 0.3011(5) 0.0347(14) Uani 1 1 d . . . . .
C7 C 0.3500(9) -0.1494(6) 0.2543(5) 0.0344(14) Uani 1 1 d . . . . .
C8 C 0.3899(10) -0.2987(6) 0.2678(5) 0.0425(17) Uani 1 1 d . . . . .
H8 H 0.3388 -0.3357 0.2273 0.051 Uiso 1 1 calc R . . . .
C14 C -0.2203(9) 0.1118(7) 0.4143(5) 0.0366(14) Uani 1 1 d . . . . .
H14 H -0.3140 0.0858 0.4321 0.044 Uiso 1 1 calc R . . . .
C9 C 0.5046(11) -0.3888(7) 0.3412(6) 0.057(2) Uani 1 1 d . . . . .
H9 H 0.5316 -0.4872 0.3494 0.068 Uiso 1 1 calc R . . . .
O5 O 0.4388(7) 0.1183(6) 0.3463(5) 0.0661(16) Uani 1 1 d . . . . .
C12 C -0.1318(9) 0.0157(7) 0.2411(5) 0.0393(15) Uani 1 1 d . . . . .
H12A H -0.0969 0.0556 0.1713 0.059 Uiso 1 1 calc GR . . . .
H12B H -0.2489 0.0291 0.2421 0.059 Uiso 1 1 calc GR . . . .
H12C H -0.0643 -0.0850 0.2559 0.059 Uiso 1 1 calc GR . . . .
C11 C 0.5434(8) -0.1898(7) 0.3920(5) 0.0407(16) Uani 1 1 d . . . . .
H11 H 0.5949 -0.1541 0.4332 0.049 Uiso 1 1 calc R . . . .
C10 C 0.5813(10) -0.3366(8) 0.4032(6) 0.053(2) Uani 1 1 d . . . . .
H10 H 0.6585 -0.3999 0.4526 0.063 Uiso 1 1 calc R . . . .
C17 C 0.0732(10) 0.2645(9) 0.4556(7) 0.055(2) Uani 1 1 d . . . . .
H17A H 0.0038 0.3639 0.4567 0.082 Uiso 1 1 calc GR . . . .
H17B H 0.1729 0.2573 0.4090 0.082 Uiso 1 1 calc GR . . . .
H17C H 0.1055 0.2179 0.5273 0.082 Uiso 1 1 calc GR . . . .
C21 C 0.000(2) 0.369(2) 0.1222(17) 0.048(6) Uani 0.560(10) 1 d D . P A 1
C24 C 0.290(2) 0.286(3) 0.0780(15) 0.057(8) Uani 0.560(10) 1 d D . P A 1
C25 C 0.2144(19) 0.2298(13) 0.0164(11) 0.029(3) Uani 0.560(10) 1 d D . P A 1
C26 C 0.0355(19) 0.2823(15) 0.0413(12) 0.031(3) Uani 0.560(10) 1 d D . P A 1
C23 C 0.156(3) 0.3791(16) 0.1402(14) 0.049(5) Uani 0.560(10) 1 d D . P A 1
C35 C 0.296(2) 0.1358(14) -0.0695(9) 0.060(5) Uani 0.560(10) 1 d D . P A 1
H35A H 0.4166 0.0950 -0.0640 0.091 Uiso 0.560(10) 1 calc GR . P A 1
H35B H 0.2700 0.1925 -0.1394 0.091 Uiso 0.560(10) 1 calc GR . P A 1
H35C H 0.2534 0.0601 -0.0595 0.091 Uiso 0.560(10) 1 calc GR . P A 1
C3 C -0.088(2) 0.2480(16) -0.0091(13) 0.067(5) Uani 0.560(10) 1 d D . P A 1
H3A H -0.1913 0.2675 0.0359 0.100 Uiso 0.560(10) 1 calc GR . P A 1
H3B H -0.0416 0.1483 -0.0166 0.100 Uiso 0.560(10) 1 calc GR . P A 1
H3C H -0.1118 0.3059 -0.0789 0.100 Uiso 0.560(10) 1 calc GR . P A 1
C29 C -0.169(2) 0.4507(16) 0.1672(15) 0.073(6) Uani 0.560(10) 1 d D . P A 1
H29A H -0.2414 0.3981 0.1709 0.109 Uiso 0.560(10) 1 calc GR . P A 1
H29B H -0.2161 0.5418 0.1218 0.109 Uiso 0.560(10) 1 calc GR . P A 1
H29C H -0.1605 0.4656 0.2383 0.109 Uiso 0.560(10) 1 calc GR . P A 1
C33 C 0.467(2) 0.282(2) 0.0647(17) 0.102(10) Uani 0.560(10) 1 d D . P A 1
H33A H 0.5131 0.2564 0.1342 0.154 Uiso 0.560(10) 1 calc GR . P A 1
H33B H 0.4665 0.3743 0.0313 0.154 Uiso 0.560(10) 1 calc GR . P A 1
H33C H 0.5343 0.2114 0.0202 0.154 Uiso 0.560(10) 1 calc GR . P A 1
C31 C 0.181(4) 0.4767(18) 0.2061(13) 0.109(10) Uani 0.560(10) 1 d D . P A 1
H31A H 0.2988 0.4602 0.2038 0.164 Uiso 0.560(10) 1 calc R . P A 1
H31B H 0.1185 0.5749 0.1768 0.164 Uiso 0.560(10) 1 calc R . P A 1
H31C H 0.1402 0.4568 0.2795 0.164 Uiso 0.560(10) 1 calc R . P A 1
C36 C 0.117(3) 0.1794(19) -0.0478(13) 0.066(7) Uani 0.440(10) 1 d D . P A 2
H36A H 0.1809 0.0788 -0.0268 0.100 Uiso 0.440(10) 1 calc GR . P A 2
H36B H 0.1597 0.2115 -0.1179 0.100 Uiso 0.440(10) 1 calc GR . P A 2
H36C H 0.0001 0.1952 -0.0501 0.100 Uiso 0.440(10) 1 calc GR . P A 2
C20 C 0.135(3) 0.2607(18) 0.0317(13) 0.034(5) Uani 0.440(10) 1 d D . P A 2
C27 C 0.0059(18) 0.347(2) 0.0992(18) 0.030(6) Uani 0.440(10) 1 d D . P A 2
C28 C -0.179(2) 0.383(3) 0.1057(19) 0.075(8) Uani 0.440(10) 1 d D . P A 2
H28A H -0.2039 0.3262 0.0636 0.113 Uiso 0.440(10) 1 calc GR . P A 2
H28B H -0.2353 0.4831 0.0781 0.113 Uiso 0.440(10) 1 calc GR . P A 2
H28C H -0.2177 0.3637 0.1795 0.113 Uiso 0.440(10) 1 calc GR . P A 2
C22 C 0.089(3) 0.3869(15) 0.1728(11) 0.033(5) Uani 0.440(10) 1 d D . P A 2
C30 C -0.001(2) 0.4987(14) 0.2464(11) 0.048(5) Uani 0.440(10) 1 d D . P A 2
H30A H -0.0589 0.4595 0.3062 0.073 Uiso 0.440(10) 1 calc GR . P A 2
H30B H -0.0811 0.5822 0.2067 0.073 Uiso 0.440(10) 1 calc GR . P A 2
H30C H 0.0810 0.5249 0.2726 0.073 Uiso 0.440(10) 1 calc GR . P A 2
C32 C 0.394(3) 0.3713(18) 0.1871(18) 0.069(7) Uani 0.440(10) 1 d D . P A 2
H32A H 0.3497 0.4040 0.2550 0.103 Uiso 0.440(10) 1 calc GR . P A 2
H32B H 0.4179 0.4457 0.1374 0.103 Uiso 0.440(10) 1 calc GR . P A 2
H32C H 0.4955 0.2874 0.1975 0.103 Uiso 0.440(10) 1 calc GR . P A 2
C18 C 0.266(2) 0.3357(17) 0.1430(15) 0.035(4) Uani 0.440(10) 1 d D . P A 2
C19 C 0.292(2) 0.261(2) 0.0553(18) 0.029(5) Uani 0.440(10) 1 d D U P A 2
C34 C 0.464(2) 0.1915(17) -0.0014(17) 0.067(7) Uani 0.440(10) 1 d D . P A 2
H34A H 0.5401 0.1215 0.0498 0.101 Uiso 0.440(10) 1 calc GR . P A 2
H34B H 0.5094 0.2638 -0.0325 0.101 Uiso 0.440(10) 1 calc GR . P A 2
H34C H 0.4527 0.1454 -0.0573 0.101 Uiso 0.440(10) 1 calc GR . P A 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 O3 2.091(4) . ?
Ir1 C2 2.035(6) . ?
Ir1 C4 2.023(7) . ?
Ir1 C21 2.25(2) . ?
Ir1 C24 2.179(18) . ?
Ir1 C25 2.302(13) . ?
Ir1 C23 2.190(13) . ?
Ir1 C20 2.193(16) . ?
Ir1 C27 2.230(18) . ?
Ir1 C22 2.154(14) . ?
Ir1 C18 2.186(16) . ?
Ir1 C19 2.21(2) . ?
O3 C7 1.324(8) . ?
N16 C15 1.369(8) . ?
N16 C2 1.356(7) . ?
N16 C17 1.454(9) . ?
C15 C14 1.350(10) . ?
N13 C2 1.342(8) . ?
N13 C14 1.392(7) . ?
N13 C12 1.463(8) . ?
C6 C4 1.451(9) . ?
C6 C7 1.401(9) . ?
C6 C11 1.380(9) . ?
C4 O5 1.242(8) . ?
C7 C8 1.411(8) . ?
C8 C9 1.371(11) . ?
C9 C10 1.384(12) . ?
C11 C10 1.390(10) . ?
C21 C26 1.411(17) . ?
C21 C23 1.43(2) . ?
C21 C29 1.469(17) . ?
C24 C25 1.40(2) . ?
C24 C23 1.43(2) . ?
C24 C33 1.487(19) . ?
C25 C26 1.430(17) . ?
C25 C35 1.513(16) . ?
C26 C3 1.491(16) . ?
C23 C31 1.510(16) . ?
C36 C20 1.484(17) . ?
C20 C27 1.425(19) . ?
C20 C19 1.42(2) . ?
C27 C28 1.478(18) . ?
C27 C22 1.45(2) . ?
C22 C30 1.522(15) . ?
C22 C18 1.43(2) . ?
C32 C18 1.48(2) . ?
C18 C19 1.42(2) . ?
C19 C34 1.522(18) . ?

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
O3 Ir1 C21 134.1(6) . . ?
O3 Ir1 C24 119.7(7) . . ?
O3 Ir1 C25 94.7(4) . . ?
O3 Ir1 C23 155.4(5) . . ?
O3 Ir1 C20 100.9(4) . . ?
O3 Ir1 C27 125.3(6) . . ?
O3 Ir1 C22 163.6(5) . . ?
O3 Ir1 C18 143.2(5) . . ?
O3 Ir1 C19 110.0(5) . . ?
C2 Ir1 O3 88.8(2) . . ?
C2 Ir1 C21 91.9(5) . . ?
C2 Ir1 C24 150.4(7) . . ?
C2 Ir1 C25 144.0(5) . . ?
C2 Ir1 C23 112.1(6) . . ?
C2 Ir1 C20 128.3(6) . . ?
C2 Ir1 C27 96.6(6) . . ?
C2 Ir1 C22 95.1(5) . . ?
C2 Ir1 C18 127.4(5) . . ?
C2 Ir1 C19 157.1(5) . . ?
C4 Ir1 O3 80.4(2) . . ?
C4 Ir1 C2 89.8(2) . . ?
C4 Ir1 C21 145.4(6) . . ?
C4 Ir1 C24 101.6(5) . . ?
C4 Ir1 C25 126.2(4) . . ?
C4 Ir1 C23 111.1(5) . . ?
C4 Ir1 C20 141.8(6) . . ?
C4 Ir1 C27 153.5(6) . . ?
C4 Ir1 C22 115.4(6) . . ?
C4 Ir1 C18 92.1(5) . . ?
C4 Ir1 C19 105.7(6) . . ?
C21 Ir1 C25 60.5(5) . . ?
C24 Ir1 C21 63.3(7) . . ?
C24 Ir1 C25 36.4(6) . . ?
C24 Ir1 C23 38.3(7) . . ?
C23 Ir1 C21 37.6(6) . . ?
C23 Ir1 C25 60.9(5) . . ?
C20 Ir1 C27 37.6(5) . . ?
C20 Ir1 C19 37.5(6) . . ?
C22 Ir1 C20 64.2(5) . . ?
C22 Ir1 C27 38.5(6) . . ?
C22 Ir1 C18 38.5(6) . . ?
C22 Ir1 C19 63.2(6) . . ?
C18 Ir1 C20 63.8(6) . . ?
C18 Ir1 C27 63.7(7) . . ?
C18 Ir1 C19 37.6(6) . . ?
C19 Ir1 C27 62.2(7) . . ?
C7 O3 Ir1 112.2(4) . . ?
C15 N16 C17 121.9(5) . . ?
C2 N16 C15 111.1(6) . . ?
C2 N16 C17 127.1(6) . . ?
C14 C15 N16 107.6(5) . . ?
C2 N13 C14 111.9(5) . . ?
C2 N13 C12 127.0(5) . . ?
C14 N13 C12 121.2(6) . . ?
C7 C6 C4 113.8(6) . . ?
C11 C6 C4 124.2(6) . . ?
C11 C6 C7 121.9(6) . . ?
N16 C2 Ir1 128.5(5) . . ?
N13 C2 Ir1 126.6(4) . . ?
N13 C2 N16 104.2(5) . . ?
C6 C4 Ir1 112.8(4) . . ?
O5 C4 Ir1 125.5(5) . . ?
O5 C4 C6 121.7(7) . . ?
O3 C7 C6 120.1(5) . . ?
O3 C7 C8 121.6(6) . . ?
C6 C7 C8 118.3(6) . . ?
C9 C8 C7 119.4(7) . . ?
C15 C14 N13 105.2(6) . . ?
C8 C9 C10 121.5(7) . . ?
C6 C11 C10 118.6(7) . . ?
C9 C10 C11 120.2(7) . . ?
C26 C21 Ir1 77.1(10) . . ?
C26 C21 C23 107.3(13) . . ?
C26 C21 C29 126.0(19) . . ?
C23 C21 Ir1 68.7(9) . . ?
C23 C21 C29 126(2) . . ?
C29 C21 Ir1 126.5(14) . . ?
C25 C24 Ir1 76.6(10) . . ?
C25 C24 C23 106.7(14) . . ?
C25 C24 C33 128(2) . . ?
C23 C24 Ir1 71.2(9) . . ?
C23 C24 C33 124(2) . . ?
C33 C24 Ir1 128.1(13) . . ?
C24 C25 Ir1 67.0(10) . . ?
C24 C25 C26 109.4(14) . . ?
C24 C25 C35 128.7(18) . . ?
C26 C25 Ir1 75.2(8) . . ?
C26 C25 C35 121.8(17) . . ?
C35 C25 Ir1 127.2(8) . . ?
C21 C26 Ir1 67.5(10) . . ?
C21 C26 C25 107.8(13) . . ?
C21 C26 C3 127.0(17) . . ?
C25 C26 Ir1 69.3(8) . . ?
C25 C26 C3 125.2(17) . . ?
C3 C26 Ir1 127.8(9) . . ?
C21 C23 Ir1 73.6(10) . . ?
C21 C23 C24 108.5(13) . . ?
C21 C23 C31 128(2) . . ?
C24 C23 Ir1 70.4(9) . . ?
C24 C23 C31 124(2) . . ?
C31 C23 Ir1 124.9(10) . . ?
C36 C20 Ir1 119.5(12) . . ?
C27 C20 Ir1 72.6(10) . . ?
C27 C20 C36 128(2) . . ?
C19 C20 Ir1 72.0(12) . . ?
C19 C20 C36 124(2) . . ?
C19 C20 C27 107.7(13) . . ?
C20 C27 Ir1 69.8(9) . . ?
C20 C27 C28 130(2) . . ?
C20 C27 C22 107.2(12) . . ?
C28 C27 Ir1 123.1(15) . . ?
C22 C27 Ir1 67.9(9) . . ?
C22 C27 C28 123(2) . . ?
C27 C22 Ir1 73.6(10) . . ?
C27 C22 C30 124.9(19) . . ?
C30 C22 Ir1 133.3(10) . . ?
C18 C22 Ir1 72.0(8) . . ?
C18 C22 C27 108.1(13) . . ?
C18 C22 C30 124.8(19) . . ?
C22 C18 Ir1 69.5(9) . . ?
C22 C18 C32 125.6(18) . . ?
C32 C18 Ir1 129.1(12) . . ?
C19 C18 Ir1 72.3(12) . . ?
C19 C18 C22 107.0(15) . . ?
C19 C18 C32 127(2) . . ?
C20 C19 Ir1 70.4(11) . . ?
C20 C19 C34 127(2) . . ?
C18 C19 Ir1 70.1(11) . . ?
C18 C19 C20 109.6(15) . . ?
C18 C19 C34 124(2) . . ?
C34 C19 Ir1 125.2(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.504
_oxdiff_exptl_absorpt_empirical_full_min 0.630
####################################################################### 
# 
# 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_str2049
_database_code_depnum_ccdc_archive 'CCDC 1850451'
_audit_update_record             
;
2018-06-19 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;
_audit_creation_date             2018-04-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H27 Ir N2 O2, 2(C F3 O3 S), C H2 Cl2'
_chemical_formula_sum            'C18 H29 Cl2 F6 Ir N2 O8 S2'
_chemical_formula_weight         842.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C47 H65 N2 O22 Ir S F'
_chemical_oxdiff_usercomment     'MB 226'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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                   11.2529(5)
_cell_length_b                   21.6653(7)
_cell_length_c                   12.9575(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.582(5)
_cell_angle_gamma                90
_cell_volume                     2937.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22946
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      29.0080
_cell_measurement_theta_min      3.1320
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.950
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.459
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1648
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -31 0 0.0535
-15 1 0 0.0462
-9 -8 17 0.2044
-8 6 18 0.1846
-2 30 0 0.0394
3 9 -17 0.3488
15 -1 0 0.0350
7 -6 -18 0.3470

_exptl_crystal_size_max          0.568
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.081
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0078 -31.0032 -0.0059 0.2486 0.9429 0.2900
-15.0087 1.0012 -0.0035 0.9860 -0.2427 0.0699
-8.9775 -8.0011 16.9878 0.1588 -0.0454 0.9817
-7.9719 6.0002 17.9901 -0.0182 -0.4732 0.8985
-1.9942 30.0033 0.0050 -0.0444 -0.9544 -0.2650
2.9741 9.0017 -16.9891 0.2321 -0.0702 -0.9593
15.0087 -1.0012 0.0035 -0.9860 0.2427 -0.0699
6.9713 -6.0001 -17.9903 0.0844 0.4591 -0.8932

_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            58882
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.528
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4051
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -55.00   0.50    2.50    --  -11.28 178.00  60.00   90
  2  ω    -20.00  31.00   0.50    2.50    --  -11.28 -99.00   0.00  102
  3  ω    -64.00  38.00   0.50    2.50    --   12.14 -37.00-150.00  204
  4  ω    -17.00  86.00   0.50    2.50    --   12.14  57.00 -60.00  206
  5  ω    -34.00  94.00   0.50    2.50    --   12.14  19.00  30.00  256
  6  ω    -20.00  31.00   0.50    2.50    --  -11.28 -99.00  30.00  102
  7  ω    -74.00 -29.00   0.50    2.50    --  -11.28 133.00  34.98   90
  8  ω     35.00  86.00   0.50    2.50    --   12.14 178.00 150.00  102
  9  ω      3.00  70.00   0.50    2.50    --   12.14-126.00 -66.30  134
 10  ω    -14.00  88.00   0.50    2.50    --   12.14  37.00-150.00  204
 11  ω     34.00 101.00   0.50    2.50    --   12.14-178.00  90.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0660795000
_diffrn_orient_matrix_UB_12      -0.0058662000
_diffrn_orient_matrix_UB_13      -0.0283385000
_diffrn_orient_matrix_UB_21      0.0141141000
_diffrn_orient_matrix_UB_22      -0.0308715000
_diffrn_orient_matrix_UB_23      -0.0097524000
_diffrn_orient_matrix_UB_31      -0.0052806000
_diffrn_orient_matrix_UB_32      -0.0091932000
_diffrn_orient_matrix_UB_33      0.0506700000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5442
_reflns_number_total             5992
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         1.719
_refine_diff_density_min         -1.394
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5992
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.060
_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)+(0.0344P)²+9.4215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0769
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C12) \\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.05 and sigma for
terminal atoms of 0.2
Uanis(C19) \\sim Ueq: with sigma of 0.051 and sigma for terminal atoms of 0.2
Uanis(C18) \\sim Ueq: with sigma of 0.5 and sigma for terminal atoms of 0.2
Uanis(C12) = Uanis(C20)
Uanis(C19) = Uanis(C20)
Uanis(C12) = Uanis(C11)
3.a Rotating group:
 O9(H9A,H9B), O10(H10A,H10B)
3.b Secondary CH2 refined with riding coordinates:
 C37(H37A,H37B)
3.c Me refined with riding coordinates:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C14(H14A,H14B,H14C), C12(H12A,H12B,
 H12C), C20(H20A,H20B,H20C)
3.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6)
3.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.04570(2) 0.41902(2) 0.76481(2) 0.02549(7) Uani 1 1 d . . . . .
S33 S 0.74716(11) 0.38954(5) 0.18066(10) 0.0358(2) Uani 1 1 d . . . . .
S25 S 0.76876(12) 0.58782(6) 0.71980(11) 0.0390(3) Uani 1 1 d . . . . .
Cl38 Cl 0.5434(2) 0.23140(11) 0.3631(2) 0.0981(6) Uani 1 1 d . . . . .
Cl39 Cl 0.4398(3) 0.21391(11) 0.1254(2) 0.1036(7) Uani 1 1 d . . . . .
O9 O 0.0444(3) 0.49137(14) 0.8808(2) 0.0311(6) Uani 1 1 d . . . . .
H9A H 0.0686 0.4769 0.9481 0.047 Uiso 1 1 d GR . . . .
H9B H -0.0321 0.5064 0.8632 0.047 Uiso 1 1 d GR . . . .
O10 O 0.0095(3) 0.49763(14) 0.6534(2) 0.0351(7) Uani 1 1 d . . . . .
H10A H 0.0051 0.4857 0.5887 0.053 Uiso 1 1 d GR . . . .
H10B H 0.0704 0.5244 0.6784 0.053 Uiso 1 1 d GR . . . .
F30 F 0.8006(4) 0.28116(16) 0.2743(3) 0.0731(11) Uani 1 1 d . . . . .
F23 F 0.5319(3) 0.58098(18) 0.7072(3) 0.0667(10) Uani 1 1 d . . . . .
F22 F 0.5528(4) 0.6082(2) 0.5572(3) 0.0825(12) Uani 1 1 d . . . . .
N3 N 0.3023(4) 0.43986(17) 0.7357(3) 0.0318(8) Uani 1 1 d . . . . .
F24 F 0.5811(4) 0.51423(19) 0.6099(4) 0.0879(13) Uani 1 1 d . . . . .
O26 O 0.8063(3) 0.54170(19) 0.8062(3) 0.0489(9) Uani 1 1 d . . . . .
O28 O 0.7699(4) 0.6494(2) 0.7583(4) 0.0717(13) Uani 1 1 d . . . . .
O34 O 0.7828(4) 0.41907(15) 0.0957(3) 0.0460(9) Uani 1 1 d . . . . .
O36 O 0.6148(3) 0.37491(18) 0.1478(4) 0.0562(10) Uani 1 1 d . . . . .
O27 O 0.8243(4) 0.5783(2) 0.6372(3) 0.0615(12) Uani 1 1 d . . . . .
N7 N 0.3307(3) 0.43270(17) 0.9083(3) 0.0301(8) Uani 1 1 d . . . . .
F31 F 0.7836(4) 0.28242(17) 0.1041(3) 0.0810(12) Uani 1 1 d . . . . .
O35 O 0.8049(4) 0.41698(15) 0.2891(3) 0.0482(9) Uani 1 1 d . . . . .
F32 F 0.9488(3) 0.32006(19) 0.2282(4) 0.0891(15) Uani 1 1 d . . . . .
C5 C 0.4327(5) 0.4421(2) 0.7950(4) 0.0413(11) Uani 1 1 d . . . . .
H5 H 0.4961 0.4460 0.7654 0.050 Uiso 1 1 calc R . . . .
C8 C 0.3114(5) 0.4286(2) 1.0134(4) 0.0417(11) Uani 1 1 d . . . . .
H8A H 0.3705 0.3994 1.0610 0.063 Uiso 1 1 calc GR . . . .
H8B H 0.2256 0.4154 0.9999 0.063 Uiso 1 1 calc GR . . . .
H8C H 0.3254 0.4684 1.0485 0.063 Uiso 1 1 calc GR . . . .
C4 C 0.2482(5) 0.4437(3) 0.6148(4) 0.0458(12) Uani 1 1 d . . . . .
H4A H 0.2645 0.4839 0.5917 0.069 Uiso 1 1 calc GR . . . .
H4B H 0.1577 0.4368 0.5891 0.069 Uiso 1 1 calc GR . . . .
H4C H 0.2869 0.4129 0.5839 0.069 Uiso 1 1 calc GR . . . .
C21 C 0.6002(5) 0.5721(3) 0.6441(4) 0.0463(12) Uani 1 1 d . . . . .
C29 C 0.8246(5) 0.3142(2) 0.1981(5) 0.0498(13) Uani 1 1 d . . . . .
C6 C 0.4507(4) 0.4376(2) 0.9021(4) 0.0400(11) Uani 1 1 d . . . . .
H6 H 0.5288 0.4377 0.9614 0.048 Uiso 1 1 calc R . . . .
C15 C -0.1275(5) 0.3689(2) 0.7552(6) 0.0577(16) Uani 1 1 d . . . . .
C13 C -0.0222(7) 0.3463(2) 0.8400(5) 0.0585(16) Uani 1 1 d . . . . .
C37 C 0.4713(6) 0.2667(3) 0.2335(6) 0.0634(17) Uani 1 1 d . . . . .
H37A H 0.3919 0.2859 0.2297 0.076 Uiso 1 1 calc R . . . .
H37B H 0.5271 0.2988 0.2252 0.076 Uiso 1 1 calc R . . . .
C11 C 0.0627(7) 0.3231(3) 0.7913(14) 0.154(4) Uani 1 1 d . . . . .
C19 C 0.0037(16) 0.3369(5) 0.6736(13) 0.169(5) Uani 1 1 d . U . . .
C16 C -0.2424(9) 0.3936(4) 0.7803(14) 0.164(7) Uani 1 1 d . . . . .
H16A H -0.2235 0.3918 0.8588 0.246 Uiso 1 1 calc R . . . .
H16B H -0.2590 0.4356 0.7555 0.246 Uiso 1 1 calc R . . . .
H16C H -0.3163 0.3688 0.7423 0.246 Uiso 1 1 calc R . . . .
C18 C -0.2100(15) 0.3841(6) 0.5472(9) 0.234(11) Uani 1 1 d . U . . .
H18A H -0.1764 0.3747 0.4908 0.351 Uiso 1 1 calc R . . . .
H18B H -0.2894 0.3627 0.5316 0.351 Uiso 1 1 calc R . . . .
H18C H -0.2241 0.4278 0.5482 0.351 Uiso 1 1 calc R . . . .
C2 C 0.2382(4) 0.43417(18) 0.8048(3) 0.0261(8) Uani 1 1 d . . . . .
C17 C -0.1156(7) 0.3639(3) 0.6590(5) 0.072(2) Uani 1 1 d . . . . .
C14 C -0.0065(16) 0.3433(5) 0.9594(8) 0.189(8) Uani 1 1 d . . . . .
H14A H 0.0752 0.3256 1.0017 0.284 Uiso 1 1 calc R . . . .
H14B H -0.0115 0.3842 0.9860 0.284 Uiso 1 1 calc R . . . .
H14C H -0.0730 0.3182 0.9671 0.284 Uiso 1 1 calc R . . . .
C12 C 0.1851(7) 0.2889(3) 0.8529(11) 0.154(4) Uani 1 1 d . U . . .
H12A H 0.2260 0.2779 0.8022 0.231 Uiso 1 1 calc R . . . .
H12B H 0.2410 0.3148 0.9104 0.231 Uiso 1 1 calc R . . . .
H12C H 0.1662 0.2522 0.8853 0.231 Uiso 1 1 calc R . . . .
C20 C 0.0517(12) 0.3162(4) 0.5865(11) 0.169(5) Uani 1 1 d . U . . .
H20A H 0.1362 0.2996 0.6211 0.254 Uiso 1 1 calc R . . . .
H20B H -0.0041 0.2849 0.5417 0.254 Uiso 1 1 calc R . . . .
H20C H 0.0537 0.3506 0.5406 0.254 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
Ir1 O9 2.176(3) . ?
Ir1 O10 2.172(3) . ?
Ir1 C15 2.193(5) . ?
Ir1 C13 2.136(5) . ?
Ir1 C11 2.103(7) . ?
Ir1 C19 2.092(7) . ?
Ir1 C2 2.060(4) . ?
Ir1 C17 2.184(6) . ?
S33 O34 1.451(4) . ?
S33 O36 1.426(4) . ?
S33 O35 1.441(4) . ?
S33 C29 1.826(5) . ?
S25 O26 1.443(4) . ?
S25 O28 1.424(4) . ?
S25 O27 1.439(4) . ?
S25 C21 1.818(6) . ?
Cl38 C37 1.749(7) . ?
Cl39 C37 1.741(7) . ?
F30 C29 1.324(7) . ?
F23 C21 1.327(6) . ?
F22 C21 1.312(6) . ?
N3 C5 1.384(6) . ?
N3 C4 1.460(6) . ?
N3 C2 1.346(5) . ?
F24 C21 1.322(7) . ?
N7 C8 1.459(6) . ?
N7 C6 1.386(6) . ?
N7 C2 1.363(5) . ?
F31 C29 1.325(7) . ?
F32 C29 1.312(6) . ?
C5 C6 1.330(7) . ?
C15 C13 1.376(9) . ?
C15 C16 1.540(10) . ?
C15 C17 1.306(10) . ?
C13 C11 1.417(15) . ?
C13 C14 1.492(10) . ?
C11 C19 1.453(19) . ?
C11 C12 1.508(10) . ?
C19 C17 1.412(16) . ?
C19 C20 1.487(10) . ?
C18 C17 1.512(10) . ?

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
O9 Ir1 C15 99.4(2) . . ?
O9 Ir1 C17 127.8(3) . . ?
O10 Ir1 O9 81.19(12) . . ?
O10 Ir1 C15 113.87(19) . . ?
O10 Ir1 C17 95.88(19) . . ?
C13 Ir1 O9 97.02(19) . . ?
C13 Ir1 O10 150.5(2) . . ?
C13 Ir1 C15 37.0(2) . . ?
C13 Ir1 C17 61.9(2) . . ?
C11 Ir1 O9 128.5(5) . . ?
C11 Ir1 O10 150.1(5) . . ?
C11 Ir1 C15 63.0(3) . . ?
C11 Ir1 C13 39.0(4) . . ?
C11 Ir1 C17 64.3(3) . . ?
C19 Ir1 O9 161.1(2) . . ?
C19 Ir1 O10 110.1(5) . . ?
C19 Ir1 C15 62.4(3) . . ?
C19 Ir1 C13 65.5(4) . . ?
C19 Ir1 C11 40.5(5) . . ?
C19 Ir1 C17 38.5(5) . . ?
C2 Ir1 O9 89.13(14) . . ?
C2 Ir1 O10 88.00(14) . . ?
C2 Ir1 C15 157.40(19) . . ?
C2 Ir1 C13 121.5(2) . . ?
C2 Ir1 C11 95.3(2) . . ?
C2 Ir1 C19 106.0(4) . . ?
C2 Ir1 C17 143.1(3) . . ?
C17 Ir1 C15 34.7(3) . . ?
O34 S33 C29 103.6(2) . . ?
O36 S33 O34 114.9(2) . . ?
O36 S33 O35 115.4(3) . . ?
O36 S33 C29 103.7(2) . . ?
O35 S33 O34 114.0(2) . . ?
O35 S33 C29 103.0(2) . . ?
O26 S25 C21 103.8(2) . . ?
O28 S25 O26 114.5(3) . . ?
O28 S25 O27 116.4(3) . . ?
O28 S25 C21 103.7(3) . . ?
O27 S25 O26 113.2(2) . . ?
O27 S25 C21 102.9(3) . . ?
C5 N3 C4 122.2(4) . . ?
C2 N3 C5 110.6(4) . . ?
C2 N3 C4 127.2(4) . . ?
C6 N7 C8 122.8(4) . . ?
C2 N7 C8 126.7(4) . . ?
C2 N7 C6 110.4(4) . . ?
C6 C5 N3 107.5(4) . . ?
F23 C21 S25 111.5(4) . . ?
F22 C21 S25 111.5(4) . . ?
F22 C21 F23 107.4(5) . . ?
F22 C21 F24 108.3(5) . . ?
F24 C21 S25 111.5(4) . . ?
F24 C21 F23 106.5(5) . . ?
F30 C29 S33 110.9(4) . . ?
F30 C29 F31 107.9(5) . . ?
F31 C29 S33 111.2(4) . . ?
F32 C29 S33 110.9(4) . . ?
F32 C29 F30 108.5(5) . . ?
F32 C29 F31 107.3(5) . . ?
C5 C6 N7 106.7(4) . . ?
C13 C15 Ir1 69.2(3) . . ?
C13 C15 C16 119.9(8) . . ?
C16 C15 Ir1 127.9(5) . . ?
C17 C15 Ir1 72.2(3) . . ?
C17 C15 C13 111.8(6) . . ?
C17 C15 C16 128.2(9) . . ?
C15 C13 Ir1 73.7(3) . . ?
C15 C13 C11 107.1(7) . . ?
C15 C13 C14 125.5(9) . . ?
C11 C13 Ir1 69.2(4) . . ?
C11 C13 C14 127.2(10) . . ?
C14 C13 Ir1 125.3(5) . . ?
Cl39 C37 Cl38 111.8(3) . . ?
C13 C11 Ir1 71.7(4) . . ?
C13 C11 C19 105.8(7) . . ?
C13 C11 C12 124.9(14) . . ?
C19 C11 Ir1 69.3(5) . . ?
C19 C11 C12 129.3(15) . . ?
C12 C11 Ir1 125.6(5) . . ?
C11 C19 Ir1 70.2(4) . . ?
C11 C19 C20 125.5(16) . . ?
C17 C19 Ir1 74.3(4) . . ?
C17 C19 C11 105.7(7) . . ?
C17 C19 C20 128.0(16) . . ?
C20 C19 Ir1 128.0(6) . . ?
N3 C2 Ir1 128.2(3) . . ?
N3 C2 N7 104.7(4) . . ?
N7 C2 Ir1 126.6(3) . . ?
C15 C17 Ir1 73.0(3) . . ?
C15 C17 C19 109.5(8) . . ?
C15 C17 C18 127.4(11) . . ?
C19 C17 Ir1 67.2(4) . . ?
C19 C17 C18 123.1(12) . . ?
C18 C17 Ir1 124.9(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.351
_oxdiff_exptl_absorpt_empirical_full_min 0.762
