# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1465203'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H36 N2 O S2, C2 H4 O2'
_chemical_formula_sum            'C31 H40 N2 O3 S2'
_chemical_formula_weight         552.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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

_cell_length_a                   11.1823(6)
_cell_length_b                   26.5152(14)
_cell_length_c                   11.5015(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.4590(10)
_cell_angle_gamma                90
_cell_volume                     3104.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3995
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.25

_exptl_crystal_description       'needle like'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.204
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17294
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.536
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5471
_reflns_number_gt                4135
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1550P)²+0.7849P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5471
_refine_ls_number_parameters     343
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.2209
_refine_ls_wR_factor_gt          0.2039
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
S1 S 0.66115(8) -0.04586(3) 0.60228(8) 0.0475(3) Uani 1 1 d . . . . .
S2 S 1.13878(8) 0.04785(3) 0.59325(7) 0.0468(3) Uani 1 1 d . . . . .
O1 O 1.0860(2) 0.21218(8) 1.0232(2) 0.0478(6) Uani 1 1 d . . . . .
H1A H 1.0799 0.1867 0.9763 0.072 Uiso 1 1 d R U . . .
O2 O 0.6335(2) 0.05689(11) 0.9883(2) 0.0642(7) Uani 1 1 d . . . . .
O3 O 0.4901(4) 0.03216(18) 0.7947(4) 0.1175(13) Uani 1 1 d . . . . .
H3C H 0.4065 0.0359 0.7475 0.141 Uiso 1 1 d R U . . .
N1 N 1.0074(2) 0.12704(8) 0.9123(2) 0.0333(5) Uani 1 1 d . . . . .
N2 N 0.8564(2) 0.08229(8) 0.9404(2) 0.0329(5) Uani 1 1 d . . . . .
H2A H 0.8020 0.0725 0.9711 0.039 Uiso 1 1 calc R U . . .
C1 C 1.0076(3) 0.20560(11) 1.0861(3) 0.0359(6) Uani 1 1 d . U . . .
C2 C 1.0042(3) 0.24356(11) 1.1696(3) 0.0405(7) Uani 1 1 d . U . . .
C3 C 0.9191(3) 0.23681(11) 1.2279(3) 0.0431(7) Uani 1 1 d . U . . .
H3A H 0.9151 0.2621 1.2823 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8387(3) 0.19454(11) 1.2103(3) 0.0397(7) Uani 1 1 d . U . . .
C5 C 0.8478(3) 0.15720(11) 1.1303(3) 0.0373(6) Uani 1 1 d . U . . .
H5A H 0.7971 0.1282 1.1177 0.045 Uiso 1 1 calc R U . . .
C6 C 0.9310(3) 0.16195(10) 1.0679(2) 0.0329(6) Uani 1 1 d . U . . .
C7 C 1.0868(4) 0.29173(13) 1.1889(4) 0.0575(9) Uani 1 1 d . U . . .
C8 C 1.2332(4) 0.27894(18) 1.2394(5) 0.0846(13) Uani 1 1 d . U . . .
H8A H 1.2476 0.2568 1.1804 0.102 Uiso 1 1 calc R U . . .
H8B H 1.2827 0.3094 1.2485 0.102 Uiso 1 1 calc R U . . .
H8C H 1.2610 0.2626 1.3209 0.102 Uiso 1 1 calc R U . . .
C9 C 1.0407(5) 0.32023(14) 1.0626(4) 0.0750(12) Uani 1 1 d . U . . .
H9A H 1.0499 0.2990 0.9991 0.090 Uiso 1 1 calc R U . . .
H9B H 0.9502 0.3296 1.0354 0.090 Uiso 1 1 calc R U . . .
H9C H 1.0931 0.3500 1.0738 0.090 Uiso 1 1 calc R U . . .
C10 C 1.0703(5) 0.32703(17) 1.2869(5) 0.0857(14) Uani 1 1 d . U . . .
H10A H 0.9794 0.3360 1.2585 0.103 Uiso 1 1 calc R U . . .
H10B H 1.0998 0.3102 1.3679 0.103 Uiso 1 1 calc R U . . .
H10C H 1.1215 0.3570 1.2955 0.103 Uiso 1 1 calc R U . . .
C11 C 0.7412(4) 0.19113(13) 1.2720(3) 0.0543(7) Uani 1 1 d . U . . .
C12 C 0.7795(7) 0.2240(2) 1.3879(6) 0.124(2) Uani 1 1 d . U . . .
H12A H 0.7899 0.2581 1.3657 0.149 Uiso 1 1 calc R U . . .
H12B H 0.7122 0.2227 1.4193 0.149 Uiso 1 1 calc R U . . .
H12C H 0.8609 0.2123 1.4530 0.149 Uiso 1 1 calc R U . . .
C13 C 0.6068(5) 0.2087(2) 1.1743(6) 0.1034(16) Uani 1 1 d . U . . .
H13A H 0.5802 0.1881 1.0990 0.124 Uiso 1 1 calc R U . . .
H13B H 0.5435 0.2057 1.2103 0.124 Uiso 1 1 calc R U . . .
H13C H 0.6123 0.2432 1.1521 0.124 Uiso 1 1 calc R U . . .
C14 C 0.7259(5) 0.13853(17) 1.3099(5) 0.0845(13) Uani 1 1 d . U . . .
H14A H 0.7014 0.1167 1.2370 0.101 Uiso 1 1 calc R U . . .
H14B H 0.8076 0.1273 1.3754 0.101 Uiso 1 1 calc R U . . .
H14C H 0.6590 0.1377 1.3417 0.101 Uiso 1 1 calc R U . . .
C15 C 0.9330(3) 0.12365(10) 0.9769(3) 0.0325(6) Uani 1 1 d . U . . .
C16 C 0.8796(3) 0.05826(10) 0.8455(3) 0.0327(6) Uani 1 1 d . U . . .
C17 C 0.9756(3) 0.08661(10) 0.8294(3) 0.0326(6) Uani 1 1 d . U . . .
C18 C 0.7237(3) 0.05090(12) 0.5497(3) 0.0482(8) Uani 1 1 d . U . . .
H18A H 0.6697 0.0381 0.4662 0.058 Uiso 1 1 calc R U . . .
H18B H 0.6842 0.0807 0.5656 0.058 Uiso 1 1 calc R U . . .
H18C H 0.8092 0.0590 0.5541 0.058 Uiso 1 1 calc R U . . .
C19 C 0.7364(3) 0.01195(10) 0.6476(3) 0.0372(6) Uani 1 1 d . U . . .
C20 C 0.8041(3) 0.01393(10) 0.7783(3) 0.0346(6) Uani 1 1 d . U . . .
C21 C 0.7931(3) -0.03132(11) 0.8392(3) 0.0406(7) Uani 1 1 d . U . . .
H21A H 0.8328 -0.0358 0.9273 0.049 Uiso 1 1 calc R U . . .
C22 C 0.7193(3) -0.06749(12) 0.7573(3) 0.0446(7) Uani 1 1 d . U . . .
C23 C 0.6885(4) -0.12012(14) 0.7859(4) 0.0670(10) Uani 1 1 d . U . . .
H23A H 0.6336 -0.1367 0.7076 0.080 Uiso 1 1 calc R U . . .
H23B H 0.7687 -0.1387 0.8273 0.080 Uiso 1 1 calc R U . . .
H23C H 0.6434 -0.1185 0.8410 0.080 Uiso 1 1 calc R U . . .
C24 C 1.0784(3) -0.01570(12) 0.7541(3) 0.0521(8) Uani 1 1 d . U . . .
H24A H 1.1124 -0.0384 0.7101 0.062 Uiso 1 1 calc R U . . .
H24B H 1.1332 -0.0168 0.8441 0.062 Uiso 1 1 calc R U . . .
H24C H 0.9907 -0.0256 0.7393 0.062 Uiso 1 1 calc R U . . .
C25 C 1.0767(3) 0.03661(11) 0.7058(3) 0.0367(6) Uani 1 1 d . U . . .
C26 C 1.0372(3) 0.08076(10) 0.7394(3) 0.0344(6) Uani 1 1 d . U . . .
C27 C 1.0602(3) 0.12335(12) 0.6754(3) 0.0449(7) Uani 1 1 d . U . . .
H27A H 1.0395 0.1561 0.6894 0.054 Uiso 1 1 calc R U . . .
C28 C 1.1142(3) 0.11250(13) 0.5928(3) 0.0482(8) Uani 1 1 d . U . . .
C29 C 1.1481(4) 0.14631(17) 0.5087(4) 0.0721(11) Uani 1 1 d . U . . .
H29A H 1.1853 0.1269 0.4615 0.086 Uiso 1 1 calc R U . . .
H29B H 1.0702 0.1631 0.4504 0.086 Uiso 1 1 calc R U . . .
H29C H 1.2108 0.1710 0.5597 0.086 Uiso 1 1 calc R U . . .
C30 C 0.5200(4) 0.05403(14) 0.9094(4) 0.0545(8) Uani 1 1 d . U . . .
C31 C 0.4095(4) 0.07415(17) 0.9329(4) 0.0710(11) Uani 1 1 d . U . . .
H31A H 0.3288 0.0682 0.8595 0.085 Uiso 1 1 calc R U . . .
H31B H 0.4064 0.0577 1.0059 0.085 Uiso 1 1 calc R U . . .
H31C H 0.4211 0.1098 0.9487 0.085 Uiso 1 1 calc R U . . .


_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
S1 C19 1.722(3) . ?
S1 C22 1.723(3) . ?
S2 C28 1.736(3) . ?
S2 C25 1.730(3) . ?
O1 C1 1.360(3) . ?
O1 H1A 0.8502 . ?
O2 C30 1.219(4) . ?
O3 C30 1.350(5) . ?
O3 H3C 0.8703 . ?
N1 C15 1.328(3) . ?
N1 C17 1.379(3) . ?
N2 C15 1.347(3) . ?
N2 C16 1.378(3) . ?
N2 H2A 0.8600 . ?
C1 C6 1.403(4) . ?
C1 C2 1.402(4) . ?
C2 C3 1.384(4) . ?
C2 C7 1.538(4) . ?
C3 C4 1.398(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.384(4) . ?
C4 C11 1.531(4) . ?
C5 C6 1.396(4) . ?
C5 H5A 0.9300 . ?
C6 C15 1.466(4) . ?
C7 C10 1.533(5) . ?
C7 C8 1.531(6) . ?
C7 C9 1.525(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.500(6) . ?
C11 C14 1.492(5) . ?
C11 C13 1.530(6) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 C17 1.384(4) . ?
C16 C20 1.467(4) . ?
C17 C26 1.470(4) . ?
C18 C19 1.491(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.375(4) . ?
C20 C21 1.421(4) . ?
C21 C22 1.358(4) . ?
C21 H21A 0.9300 . ?
C22 C23 1.506(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.491(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.362(4) . ?
C26 C27 1.428(4) . ?
C27 C28 1.351(4) . ?
C27 H27A 0.9300 . ?
C28 C29 1.478(5) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.471(5) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 S1 C22 93.16(14) . . ?
C28 S2 C25 93.46(14) . . ?
C1 O1 H1A 109.6 . . ?
C30 O3 H3C 109.2 . . ?
C15 N1 C17 107.0(2) . . ?
C15 N2 C16 108.6(2) . . ?
C15 N2 H2A 125.7 . . ?
C16 N2 H2A 125.7 . . ?
O1 C1 C6 121.0(2) . . ?
O1 C1 C2 118.6(2) . . ?
C6 C1 C2 120.4(2) . . ?
C3 C2 C1 117.3(3) . . ?
C3 C2 C7 122.0(3) . . ?
C1 C2 C7 120.6(3) . . ?
C2 C3 C4 124.3(3) . . ?
C2 C3 H3A 117.9 . . ?
C4 C3 H3A 117.9 . . ?
C5 C4 C3 116.8(2) . . ?
C5 C4 C11 121.9(3) . . ?
C3 C4 C11 121.3(3) . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C1 C6 C5 119.6(2) . . ?
C1 C6 C15 119.3(2) . . ?
C5 C6 C15 121.0(2) . . ?
C10 C7 C8 106.9(3) . . ?
C10 C7 C2 111.4(3) . . ?
C8 C7 C2 110.8(3) . . ?
C10 C7 C9 107.5(3) . . ?
C8 C7 C9 110.9(3) . . ?
C2 C7 C9 109.2(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C14 108.0(4) . . ?
C12 C11 C13 108.0(4) . . ?
C14 C11 C13 107.6(4) . . ?
C12 C11 C4 112.4(3) . . ?
C14 C11 C4 112.4(3) . . ?
C13 C11 C4 108.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 N2 110.2(2) . . ?
N1 C15 C6 123.5(2) . . ?
N2 C15 C6 126.2(2) . . ?
C17 C16 N2 105.4(2) . . ?
C17 C16 C20 132.3(2) . . ?
N2 C16 C20 122.1(2) . . ?
C16 C17 N1 108.8(2) . . ?
C16 C17 C26 130.7(2) . . ?
N1 C17 C26 120.4(2) . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C18 129.5(3) . . ?
C20 C19 S1 110.1(2) . . ?
C18 C19 S1 120.4(2) . . ?
C19 C20 C21 112.7(2) . . ?
C19 C20 C16 122.9(3) . . ?
C21 C20 C16 124.4(3) . . ?
C22 C21 C20 113.9(3) . . ?
C22 C21 H21A 123.0 . . ?
C20 C21 H21A 123.0 . . ?
C21 C22 C23 129.1(3) . . ?
C21 C22 S1 110.1(2) . . ?
C23 C22 S1 120.8(3) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C24 130.5(3) . . ?
C26 C25 S2 110.0(2) . . ?
C24 C25 S2 119.5(2) . . ?
C25 C26 C27 112.6(3) . . ?
C25 C26 C17 126.3(3) . . ?
C27 C26 C17 121.1(2) . . ?
C28 C27 C26 115.0(3) . . ?
C28 C27 H27A 122.5 . . ?
C26 C27 H27A 122.5 . . ?
C27 C28 C29 129.9(3) . . ?
C27 C28 S2 108.9(2) . . ?
C29 C28 S2 121.2(3) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O2 C30 O3 121.0(4) . . ?
O2 C30 C31 122.4(4) . . ?
O3 C30 C31 116.6(4) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?

_refine_diff_density_max         0.450
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.057

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1465204'
_audit_update_record             
;
2016-03-14 deposited with the CCDC.
2016-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C51 H47 F4 Ir N4 O S2, 2(C H4 O)'
_chemical_formula_sum            'C53 H55 F4 Ir N4 O3 S2'
_chemical_formula_weight         1128.33

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.9987(16)
_cell_length_b                   13.2108(16)
_cell_length_c                   17.001(2)
_cell_angle_alpha                69.213(2)
_cell_angle_beta                 69.523(2)
_cell_angle_gamma                73.873(2)
_cell_volume                     2517.4(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2933
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      22.04

_exptl_crystal_description       ??blocky??
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_F_000             1140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    2.796
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.578
_exptl_absorpt_correction_T_max  0.695
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruke Smart Aepex CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13793
_diffrn_reflns_av_unetI/netI     0.0950
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.818
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.966
_reflns_number_total             8791
_reflns_number_gt                6524
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8791
_refine_ls_number_parameters     632
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0832
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.51586(2) 1.11113(2) 0.21026(2) 0.03595(9) Uani 1 1 d . . . . .
S1 S 0.17783(17) 0.58900(15) 0.48732(14) 0.0673(6) Uani 1 1 d . . . . .
S2 S 0.11875(15) 1.08987(16) 0.47459(13) 0.0620(5) Uani 1 1 d . . . . .
F1 F 0.6117(4) 1.5110(4) 0.0069(4) 0.109(2) Uani 1 1 d . . . . .
F2 F 0.8786(3) 1.2673(4) 0.1393(3) 0.0941(17) Uani 1 1 d . . . . .
F3 F 0.4259(4) 1.2452(4) 0.4963(3) 0.0753(12) Uani 1 1 d . . . . .
F4 F 0.1711(3) 1.3884(3) 0.3318(3) 0.0834(14) Uani 1 1 d . . . . .
O1 O 0.5980(3) 1.0517(3) 0.0976(3) 0.0418(11) Uani 1 1 d . . . . .
O2 O 0.5178(6) 0.5835(5) 0.2396(5) 0.137(3) Uani 1 1 d D . . . .
H2E H 0.4751 0.5906 0.2092 0.164 Uiso 1 1 d DR U . . .
O3 O 0.3977(12) 0.6281(13) 0.1246(8) 0.305(7) Uani 1 1 d D . . . .
H3C H 0.4535 0.5995 0.0882 0.366 Uiso 1 1 d DR U . . .
N1 N 0.4487(4) 0.9606(4) 0.2584(3) 0.0386(13) Uani 1 1 d . . . . .
N2 N 0.4571(4) 0.7871(4) 0.2726(3) 0.0459(14) Uani 1 1 d . . . . .
H2A H 0.4825 0.7220 0.2666 0.055 Uiso 1 1 calc R U . . .
N3 N 0.6509(4) 1.0406(4) 0.2587(3) 0.0400(13) Uani 1 1 d . . . . .
N4 N 0.3854(4) 1.1943(4) 0.1628(4) 0.0433(13) Uani 1 1 d . . . . .
C1 C 0.6638(5) 0.9414(5) 0.3170(4) 0.0455(17) Uani 1 1 d . . . . .
H1A H 0.6054 0.9021 0.3404 0.055 Uiso 1 1 calc R U . . .
C2 C 0.7583(6) 0.8951(6) 0.3436(4) 0.0547(19) Uani 1 1 d . . . . .
H2B H 0.7647 0.8256 0.3834 0.066 Uiso 1 1 calc R U . . .
C3 C 0.8445(6) 0.9545(6) 0.3096(5) 0.058(2) Uani 1 1 d . . . . .
H3A H 0.9109 0.9245 0.3249 0.070 Uiso 1 1 calc R U . . .
C4 C 0.8307(5) 1.0580(6) 0.2529(4) 0.0511(18) Uani 1 1 d . . . . .
H4A H 0.8877 1.0989 0.2312 0.061 Uiso 1 1 calc R U . . .
C5 C 0.7341(5) 1.1023(5) 0.2278(4) 0.0402(15) Uani 1 1 d . . . . .
C6 C 0.7070(5) 1.2100(5) 0.1688(4) 0.0427(16) Uani 1 1 d . . . . .
C7 C 0.7753(6) 1.2890(6) 0.1287(5) 0.061(2) Uani 1 1 d . . . . .
C8 C 0.7461(6) 1.3891(6) 0.0722(5) 0.069(2) Uani 1 1 d . . . . .
H8A H 0.7944 1.4397 0.0440 0.083 Uiso 1 1 calc R U . . .
C9 C 0.6441(6) 1.4111(6) 0.0595(5) 0.063(2) Uani 1 1 d . . . . .
C10 C 0.5716(6) 1.3376(5) 0.0990(4) 0.0535(19) Uani 1 1 d . . . . .
H10A H 0.5020 1.3569 0.0887 0.064 Uiso 1 1 calc R U . . .
C11 C 0.6005(5) 1.2357(5) 0.1538(4) 0.0406(16) Uani 1 1 d . . . . .
C12 C 0.3750(6) 1.1915(5) 0.0872(5) 0.0536(19) Uani 1 1 d . . . . .
H12A H 0.4309 1.1474 0.0559 0.064 Uiso 1 1 calc R U . . .
C13 C 0.2875(6) 1.2495(6) 0.0545(5) 0.063(2) Uani 1 1 d . . . . .
H13A H 0.2831 1.2455 0.0023 0.076 Uiso 1 1 calc R U . . .
C14 C 0.2051(7) 1.3148(6) 0.1019(6) 0.070(2) Uani 1 1 d . . . . .
H14A H 0.1435 1.3547 0.0819 0.084 Uiso 1 1 calc R U . . .
C15 C 0.2137(6) 1.3213(5) 0.1782(5) 0.060(2) Uani 1 1 d . . . . .
H15A H 0.1584 1.3656 0.2097 0.071 Uiso 1 1 calc R U . . .
C16 C 0.3052(5) 1.2612(5) 0.2076(4) 0.0430(16) Uani 1 1 d . . . . .
C17 C 0.3286(5) 1.2573(5) 0.2867(4) 0.0429(16) Uani 1 1 d . . . . .
C18 C 0.2674(5) 1.3194(5) 0.3434(5) 0.0518(19) Uani 1 1 d . . . . .
C19 C 0.2981(6) 1.3163(6) 0.4140(5) 0.061(2) Uani 1 1 d . . . . .
H19A H 0.2558 1.3601 0.4506 0.073 Uiso 1 1 calc R U . . .
C20 C 0.3926(6) 1.2465(6) 0.4278(5) 0.0517(18) Uani 1 1 d . . . . .
C21 C 0.4587(5) 1.1816(6) 0.3753(4) 0.0476(17) Uani 1 1 d . . . . .
H21A H 0.5233 1.1356 0.3875 0.057 Uiso 1 1 calc R U . . .
C22 C 0.4279(5) 1.1854(5) 0.3025(4) 0.0392(16) Uani 1 1 d . . . . .
C23 C 0.6611(5) 0.9532(5) 0.1071(4) 0.0399(15) Uani 1 1 d . . . . .
C24 C 0.7659(5) 0.9349(5) 0.0446(4) 0.0414(16) Uani 1 1 d . . . . .
C25 C 0.8339(5) 0.8344(5) 0.0646(4) 0.0438(16) Uani 1 1 d . . . . .
H25A H 0.9043 0.8241 0.0257 0.053 Uiso 1 1 calc R U . . .
C26 C 0.8046(5) 0.7465(5) 0.1395(4) 0.0407(16) Uani 1 1 d . . . . .
C27 C 0.6977(5) 0.7612(5) 0.1927(4) 0.0425(16) Uani 1 1 d . . . . .
H27A H 0.6725 0.7025 0.2396 0.051 Uiso 1 1 calc R U . . .
C28 C 0.6258(5) 0.8622(5) 0.1780(4) 0.0389(15) Uani 1 1 d . . . . .
C29 C 0.8004(5) 1.0239(6) -0.0419(4) 0.0524(18) Uani 1 1 d . . . . .
C30 C 0.9090(6) 0.9845(7) -0.1046(5) 0.081(3) Uani 1 1 d . . . . .
H30A H 0.9678 0.9602 -0.0767 0.121 Uiso 1 1 calc R U . . .
H30B H 0.9000 0.9247 -0.1197 0.121 Uiso 1 1 calc R U . . .
H30C H 0.9275 1.0439 -0.1568 0.121 Uiso 1 1 calc R U . . .
C31 C 0.7095(6) 1.0617(6) -0.0896(4) 0.061(2) Uani 1 1 d . . . . .
H31A H 0.6398 1.0871 -0.0519 0.091 Uiso 1 1 calc R U . . .
H31B H 0.7297 1.1205 -0.1419 0.091 Uiso 1 1 calc R U . . .
H31C H 0.7021 1.0012 -0.1048 0.091 Uiso 1 1 calc R U . . .
C32 C 0.8167(6) 1.1234(6) -0.0227(5) 0.070(2) Uani 1 1 d . . . . .
H32A H 0.8735 1.1002 0.0071 0.105 Uiso 1 1 calc R U . . .
H32B H 0.8388 1.1790 -0.0768 0.105 Uiso 1 1 calc R U . . .
H32C H 0.7479 1.1528 0.0136 0.105 Uiso 1 1 calc R U . . .
C33 C 0.8874(5) 0.6401(5) 0.1614(5) 0.0549(18) Uani 1 1 d D U . . .
C34 C 0.8470(13) 0.5643(14) 0.2554(10) 0.093(5) Uani 0.532(10) 1 d D U P A 1
H34A H 0.8300 0.6044 0.2970 0.140 Uiso 0.532(10) 1 calc R U P A 1
H34B H 0.7814 0.5396 0.2608 0.140 Uiso 0.532(10) 1 calc R U P A 1
H34C H 0.9046 0.5020 0.2666 0.140 Uiso 0.532(10) 1 calc R U P A 1
C34A C 0.8333(15) 0.5390(12) 0.1988(17) 0.096(5) Uani 0.468(10) 1 d D U P A 2
H34D H 0.7701 0.5474 0.2480 0.144 Uiso 0.468(10) 1 calc R U P A 2
H34E H 0.8092 0.5301 0.1546 0.144 Uiso 0.468(10) 1 calc R U P A 2
H34F H 0.8862 0.4754 0.2174 0.144 Uiso 0.468(10) 1 calc R U P A 2
C35 C 0.9452(16) 0.6580(15) 0.2187(12) 0.093(4) Uani 0.532(10) 1 d D U P A 1
H35A H 0.8941 0.7051 0.2528 0.140 Uiso 0.532(10) 1 calc R U P A 1
H35B H 0.9685 0.5884 0.2572 0.140 Uiso 0.532(10) 1 calc R U P A 1
H35C H 1.0091 0.6916 0.1821 0.140 Uiso 0.532(10) 1 calc R U P A 1
C35A C 0.9993(13) 0.6634(16) 0.1568(16) 0.084(4) Uani 0.468(10) 1 d D U P A 2
H35D H 1.0032 0.7397 0.1272 0.125 Uiso 0.468(10) 1 calc R U P A 2
H35E H 1.0050 0.6463 0.2151 0.125 Uiso 0.468(10) 1 calc R U P A 2
H35F H 1.0596 0.6188 0.1253 0.125 Uiso 0.468(10) 1 calc R U P A 2
C36 C 0.9150(15) 0.5783(13) 0.0940(11) 0.084(4) Uani 0.532(10) 1 d D U P A 1
H36A H 0.8510 0.5907 0.0738 0.126 Uiso 0.532(10) 1 calc R U P A 1
H36B H 0.9761 0.6041 0.0453 0.126 Uiso 0.532(10) 1 calc R U P A 1
H36C H 0.9355 0.5010 0.1204 0.126 Uiso 0.532(10) 1 calc R U P A 1
C36A C 0.9883(15) 0.6288(17) 0.0830(11) 0.100(5) Uani 0.468(10) 1 d D U P A 2
H36D H 1.0216 0.6935 0.0601 0.151 Uiso 0.468(10) 1 calc R U P A 2
H36E H 1.0418 0.5655 0.1011 0.151 Uiso 0.468(10) 1 calc R U P A 2
H36F H 0.9649 0.6202 0.0384 0.151 Uiso 0.468(10) 1 calc R U P A 2
C37 C 0.5125(5) 0.8730(5) 0.2339(4) 0.0448(17) Uani 1 1 d . . . . .
C38 C 0.3527(5) 0.8220(5) 0.3235(4) 0.0403(16) Uani 1 1 d . . . . .
C39 C 0.3475(5) 0.9293(5) 0.3142(4) 0.0397(15) Uani 1 1 d . . . . .
C40 C 0.3856(8) 0.6166(8) 0.4794(7) 0.132(5) Uani 1 1 d . . . . .
H40A H 0.3733 0.5510 0.5271 0.198 Uiso 1 1 calc R U . . .
H40B H 0.4518 0.6004 0.4346 0.198 Uiso 1 1 calc R U . . .
H40C H 0.3943 0.6715 0.5003 0.198 Uiso 1 1 calc R U . . .
C41 C 0.2881(6) 0.6584(6) 0.4425(5) 0.061(2) Uani 1 1 d . . . . .
C42 C 0.2711(5) 0.7474(5) 0.3758(4) 0.0424(16) Uani 1 1 d . . . . .
C43 C 0.1668(5) 0.7593(5) 0.3621(5) 0.0553(19) Uani 1 1 d . . . . .
H43A H 0.1409 0.8173 0.3192 0.066 Uiso 1 1 calc R U . . .
C44 C 0.1079(5) 0.6790(6) 0.4169(5) 0.059(2) Uani 1 1 d . . . . .
C45 C -0.0039(6) 0.6646(7) 0.4200(6) 0.100(3) Uani 1 1 d . . . . .
H45A H -0.0244 0.5998 0.4660 0.150 Uiso 1 1 calc R U . . .
H45B H -0.0586 0.7276 0.4310 0.150 Uiso 1 1 calc R U . . .
H45C H -0.0004 0.6572 0.3649 0.150 Uiso 1 1 calc R U . . .
C46 C 0.3187(6) 0.9458(6) 0.4955(5) 0.068(2) Uani 1 1 d . . . . .
H46A H 0.2899 0.9645 0.5498 0.102 Uiso 1 1 calc R U . . .
H46B H 0.3251 0.8680 0.5072 0.102 Uiso 1 1 calc R U . . .
H46C H 0.3908 0.9663 0.4653 0.102 Uiso 1 1 calc R U . . .
C47 C 0.2415(5) 1.0056(5) 0.4401(4) 0.0459(17) Uani 1 1 d . . . . .
C48 C 0.2528(5) 1.0012(5) 0.3575(4) 0.0374(15) Uani 1 1 d . . . . .
C49 C 0.1626(5) 1.0650(5) 0.3257(5) 0.0486(17) Uani 1 1 d . . . . .
H49A H 0.1585 1.0702 0.2709 0.058 Uiso 1 1 calc R U . . .
C50 C 0.0817(5) 1.1189(5) 0.3797(5) 0.0522(19) Uani 1 1 d . . . . .
C51 C -0.0242(6) 1.1953(6) 0.3658(6) 0.085(3) Uani 1 1 d . . . . .
H51A H -0.0642 1.2202 0.4167 0.128 Uiso 1 1 calc R U . . .
H51B H -0.0065 1.2574 0.3157 0.128 Uiso 1 1 calc R U . . .
H51C H -0.0695 1.1572 0.3559 0.128 Uiso 1 1 calc R U . . .
C52 C 0.5421(12) 0.4669(10) 0.2841(9) 0.190(6) Uani 1 1 d D U . . .
H52A H 0.5480 0.4201 0.2500 0.284 Uiso 1 1 d R U . . .
H52B H 0.6115 0.4545 0.2970 0.284 Uiso 1 1 d R U . . .
H52C H 0.4838 0.4507 0.3378 0.284 Uiso 1 1 d R U . . .
C53 C 0.2993(15) 0.5964(16) 0.1783(13) 0.260(10) Uani 1 1 d D U . . .
H53A H 0.2837 0.5564 0.1477 0.390 Uiso 1 1 d R U . . .
H53B H 0.3018 0.5499 0.2360 0.390 Uiso 1 1 d R U . . .
H53C H 0.2419 0.6597 0.1829 0.390 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 C22 1.986(7) . ?
Ir1 C11 1.996(6) . ?
Ir1 N4 2.006(5) . ?
Ir1 N3 2.046(5) . ?
Ir1 O1 2.144(4) . ?
Ir1 N1 2.167(5) . ?
S1 C44 1.680(7) . ?
S1 C41 1.717(7) . ?
S2 C47 1.718(7) . ?
S2 C50 1.727(7) . ?
F1 C9 1.355(7) . ?
F2 C7 1.356(7) . ?
F3 C20 1.371(7) . ?
F4 C18 1.360(7) . ?
O1 C23 1.320(7) . ?
O2 C52 1.454(11) . ?
O2 H2E 0.8500 . ?
O3 C53 1.361(14) . ?
O3 H3C 0.8663 . ?
N1 C37 1.329(7) . ?
N1 C39 1.398(7) . ?
N2 C37 1.353(7) . ?
N2 C38 1.384(7) . ?
N2 H2A 0.8600 . ?
N3 C1 1.342(7) . ?
N3 C5 1.378(7) . ?
N4 C12 1.353(8) . ?
N4 C16 1.364(8) . ?
C1 C2 1.365(8) . ?
C1 H1A 0.9300 . ?
C2 C3 1.384(9) . ?
C2 H2B 0.9300 . ?
C3 C4 1.370(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.375(8) . ?
C4 H4A 0.9300 . ?
C5 C6 1.453(8) . ?
C6 C7 1.389(8) . ?
C6 C11 1.422(8) . ?
C7 C8 1.375(9) . ?
C8 C9 1.354(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.372(9) . ?
C10 C11 1.376(8) . ?
C10 H10A 0.9300 . ?
C12 C13 1.359(8) . ?
C12 H12A 0.9300 . ?
C13 C14 1.385(10) . ?
C13 H13A 0.9300 . ?
C14 C15 1.374(10) . ?
C14 H14A 0.9300 . ?
C15 C16 1.381(8) . ?
C15 H15A 0.9300 . ?
C16 C17 1.459(9) . ?
C17 C18 1.378(9) . ?
C17 C22 1.422(8) . ?
C18 C19 1.375(10) . ?
C19 C20 1.354(9) . ?
C19 H19A 0.9300 . ?
C20 C21 1.366(9) . ?
C21 C22 1.410(8) . ?
C21 H21A 0.9300 . ?
C23 C28 1.415(8) . ?
C23 C24 1.424(8) . ?
C24 C25 1.377(8) . ?
C24 C29 1.534(8) . ?
C25 C26 1.404(8) . ?
C25 H25A 0.9300 . ?
C26 C27 1.372(8) . ?
C26 C33 1.530(8) . ?
C27 C28 1.396(8) . ?
C27 H27A 0.9300 . ?
C28 C37 1.446(8) . ?
C29 C31 1.535(9) . ?
C29 C30 1.527(9) . ?
C29 C32 1.545(9) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 C34A 1.514(12) . ?
C33 C36 1.525(12) . ?
C33 C35 1.530(12) . ?
C33 C36A 1.526(13) . ?
C33 C35A 1.539(12) . ?
C33 C34 1.550(12) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C34A H34D 0.9600 . ?
C34A H34E 0.9600 . ?
C34A H34F 0.9600 . ?
C35 H35A 0.9600 . ?
C35 H35B 0.9600 . ?
C35 H35C 0.9600 . ?
C35A H35D 0.9600 . ?
C35A H35E 0.9600 . ?
C35A H35F 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C36A H36D 0.9600 . ?
C36A H36E 0.9600 . ?
C36A H36F 0.9600 . ?
C38 C39 1.354(8) . ?
C38 C42 1.478(8) . ?
C39 C48 1.473(8) . ?
C40 C41 1.492(10) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 C42 1.342(8) . ?
C42 C43 1.412(8) . ?
C43 C44 1.353(8) . ?
C43 H43A 0.9300 . ?
C44 C45 1.498(9) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C46 C47 1.486(9) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 C48 1.382(8) . ?
C48 C49 1.395(8) . ?
C49 C50 1.352(9) . ?
C49 H49A 0.9300 . ?
C50 C51 1.501(9) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 0.9600 . ?
C52 H52A 0.9598 . ?
C52 H52B 0.9601 . ?
C52 H52C 0.9600 . ?
C53 H53A 0.9599 . ?
C53 H53B 0.9601 . ?
C53 H53C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C22 Ir1 C11 87.2(2) . . ?
C22 Ir1 N4 80.4(2) . . ?
C11 Ir1 N4 94.4(2) . . ?
C22 Ir1 N3 96.4(2) . . ?
C11 Ir1 N3 80.8(2) . . ?
N4 Ir1 N3 174.4(2) . . ?
C22 Ir1 O1 171.2(2) . . ?
C11 Ir1 O1 89.7(2) . . ?
N4 Ir1 O1 91.6(2) . . ?
N3 Ir1 O1 91.26(18) . . ?
C22 Ir1 N1 102.1(2) . . ?
C11 Ir1 N1 170.1(2) . . ?
N4 Ir1 N1 90.60(18) . . ?
N3 Ir1 N1 94.53(18) . . ?
O1 Ir1 N1 81.60(17) . . ?
C44 S1 C41 92.5(3) . . ?
C47 S2 C50 93.4(3) . . ?
C23 O1 Ir1 119.1(4) . . ?
C52 O2 H2E 107.0 . . ?
C53 O3 H3C 133.3 . . ?
C37 N1 C39 106.9(5) . . ?
C37 N1 Ir1 118.7(4) . . ?
C39 N1 Ir1 134.4(4) . . ?
C37 N2 C38 108.3(5) . . ?
C37 N2 H2A 125.8 . . ?
C38 N2 H2A 125.8 . . ?
C1 N3 C5 118.7(5) . . ?
C1 N3 Ir1 125.6(4) . . ?
C5 N3 Ir1 115.8(4) . . ?
C12 N4 C16 118.3(6) . . ?
C12 N4 Ir1 123.8(5) . . ?
C16 N4 Ir1 117.8(4) . . ?
N3 C1 C2 123.4(6) . . ?
N3 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C1 C2 C3 118.2(6) . . ?
C1 C2 H2B 120.9 . . ?
C3 C2 H2B 120.9 . . ?
C4 C3 C2 119.2(6) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 121.0(6) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 N3 119.4(6) . . ?
C4 C5 C6 127.7(6) . . ?
N3 C5 C6 113.0(5) . . ?
C7 C6 C11 118.6(6) . . ?
C7 C6 C5 125.1(6) . . ?
C11 C6 C5 116.3(5) . . ?
F2 C7 C8 116.5(6) . . ?
F2 C7 C6 120.7(6) . . ?
C8 C7 C6 122.7(6) . . ?
C9 C8 C7 117.2(6) . . ?
C9 C8 H8A 121.4 . . ?
C7 C8 H8A 121.4 . . ?
F1 C9 C8 118.2(6) . . ?
F1 C9 C10 118.9(7) . . ?
C8 C9 C10 122.8(7) . . ?
C9 C10 C11 120.9(6) . . ?
C9 C10 H10A 119.5 . . ?
C11 C10 H10A 119.5 . . ?
C10 C11 C6 117.7(5) . . ?
C10 C11 Ir1 128.3(5) . . ?
C6 C11 Ir1 113.8(4) . . ?
N4 C12 C13 123.6(7) . . ?
N4 C12 H12A 118.2 . . ?
C13 C12 H12A 118.2 . . ?
C12 C13 C14 117.5(7) . . ?
C12 C13 H13A 121.3 . . ?
C14 C13 H13A 121.3 . . ?
C15 C14 C13 120.6(7) . . ?
C15 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C14 C15 C16 119.2(7) . . ?
C14 C15 H15A 120.4 . . ?
C16 C15 H15A 120.4 . . ?
N4 C16 C15 120.7(7) . . ?
N4 C16 C17 112.1(5) . . ?
C15 C16 C17 127.2(7) . . ?
C18 C17 C22 118.3(6) . . ?
C18 C17 C16 126.4(6) . . ?
C22 C17 C16 115.2(6) . . ?
F4 C18 C17 120.6(7) . . ?
F4 C18 C19 116.0(7) . . ?
C17 C18 C19 123.3(6) . . ?
C20 C19 C18 117.0(7) . . ?
C20 C19 H19A 121.5 . . ?
C18 C19 H19A 121.5 . . ?
C19 C20 C21 123.9(7) . . ?
C19 C20 F3 117.5(7) . . ?
C21 C20 F3 118.5(7) . . ?
C20 C21 C22 119.2(6) . . ?
C20 C21 H21A 120.4 . . ?
C22 C21 H21A 120.4 . . ?
C21 C22 C17 118.2(6) . . ?
C21 C22 Ir1 127.1(5) . . ?
C17 C22 Ir1 114.4(5) . . ?
O1 C23 C28 121.2(6) . . ?
O1 C23 C24 120.8(6) . . ?
C28 C23 C24 118.0(6) . . ?
C25 C24 C23 117.5(6) . . ?
C25 C24 C29 121.7(6) . . ?
C23 C24 C29 120.8(6) . . ?
C24 C25 C26 124.7(6) . . ?
C24 C25 H25A 117.6 . . ?
C26 C25 H25A 117.6 . . ?
C27 C26 C25 116.4(6) . . ?
C27 C26 C33 121.5(6) . . ?
C25 C26 C33 122.0(5) . . ?
C26 C27 C28 121.6(6) . . ?
C26 C27 H27A 119.2 . . ?
C28 C27 H27A 119.2 . . ?
C27 C28 C23 120.8(6) . . ?
C27 C28 C37 119.7(5) . . ?
C23 C28 C37 119.5(5) . . ?
C31 C29 C30 107.3(6) . . ?
C31 C29 C32 109.1(6) . . ?
C30 C29 C32 107.8(6) . . ?
C31 C29 C24 110.1(5) . . ?
C30 C29 C24 113.1(6) . . ?
C32 C29 C24 109.3(6) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C29 C31 H31A 109.5 . . ?
C29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 C32 H32A 109.5 . . ?
C29 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C29 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C36 C33 C35 138.4(11) . . ?
C34A C33 C36A 110.5(13) . . ?
C34A C33 C26 112.5(8) . . ?
C36 C33 C26 110.1(8) . . ?
C35 C33 C26 105.5(8) . . ?
C36A C33 C26 112.2(9) . . ?
C34A C33 C35A 134.6(12) . . ?
C36A C33 C35A 60.4(13) . . ?
C26 C33 C35A 111.6(9) . . ?
C36 C33 C34 110.5(11) . . ?
C35 C33 C34 72.6(12) . . ?
C26 C33 C34 113.5(8) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C33 C34A H34D 109.5 . . ?
C33 C34A H34E 109.5 . . ?
H34D C34A H34E 109.5 . . ?
C33 C34A H34F 109.5 . . ?
H34D C34A H34F 109.5 . . ?
H34E C34A H34F 109.5 . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C35A H35D 109.5 . . ?
C33 C35A H35E 109.5 . . ?
H35D C35A H35E 109.5 . . ?
C33 C35A H35F 109.5 . . ?
H35D C35A H35F 109.5 . . ?
H35E C35A H35F 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C33 C36A H36D 109.5 . . ?
C33 C36A H36E 109.5 . . ?
H36D C36A H36E 109.5 . . ?
C33 C36A H36F 109.5 . . ?
H36D C36A H36F 109.5 . . ?
H36E C36A H36F 109.5 . . ?
N1 C37 N2 109.7(5) . . ?
N1 C37 C28 128.5(6) . . ?
N2 C37 C28 121.8(6) . . ?
C39 C38 N2 106.4(5) . . ?
C39 C38 C42 131.4(6) . . ?
N2 C38 C42 122.2(5) . . ?
C38 C39 N1 108.7(5) . . ?
C38 C39 C48 126.2(5) . . ?
N1 C39 C48 125.1(5) . . ?
C41 C40 H40A 109.5 . . ?
C41 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C41 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C42 C41 C40 129.0(6) . . ?
C42 C41 S1 111.4(5) . . ?
C40 C41 S1 119.6(6) . . ?
C41 C42 C43 111.4(5) . . ?
C41 C42 C38 123.7(6) . . ?
C43 C42 C38 124.9(6) . . ?
C44 C43 C42 114.1(6) . . ?
C44 C43 H43A 122.9 . . ?
C42 C43 H43A 122.9 . . ?
C43 C44 C45 128.5(7) . . ?
C43 C44 S1 110.5(5) . . ?
C45 C44 S1 121.0(5) . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 H46A 109.5 . . ?
C47 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C47 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C47 C46 127.5(6) . . ?
C48 C47 S2 109.8(5) . . ?
C46 C47 S2 122.7(5) . . ?
C47 C48 C49 112.3(6) . . ?
C47 C48 C39 121.3(6) . . ?
C49 C48 C39 126.3(6) . . ?
C50 C49 C48 115.8(6) . . ?
C50 C49 H49A 122.1 . . ?
C48 C49 H49A 122.1 . . ?
C49 C50 C51 129.7(7) . . ?
C49 C50 S2 108.8(5) . . ?
C51 C50 S2 121.5(6) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O2 C52 H52A 113.6 . . ?
O2 C52 H52B 106.8 . . ?
H52A C52 H52B 109.5 . . ?
O2 C52 H52C 107.9 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
O3 C53 H53A 102.8 . . ?
O3 C53 H53B 115.1 . . ?
H53A C53 H53B 109.5 . . ?
O3 C53 H53C 110.3 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?

_refine_diff_density_max         1.265
_refine_diff_density_min         -1.311
_refine_diff_density_rms         0.114

_shelxl_version_number           2014/6



