# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1023276'
_audit_update_record             
;
2014-09-07 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O S2'
_chemical_formula_weight         380.51

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'

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

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

_cell_length_a                   10.083(4)
_cell_length_b                   15.939(7)
_cell_length_c                   11.976(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.764(11)
_cell_angle_gamma                90.00
_cell_volume                     1902.2(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    514
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      18.68

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10349
_diffrn_reflns_av_R_equivalents  0.1014
_diffrn_reflns_av_sigmaI/netI    0.1240
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3344
_reflns_number_gt                1609
_reflns_threshold_expression     >2sigma(I)

_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  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0323P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3344
_refine_ls_number_parameters     251
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.24976(13) 0.14891(9) 0.48164(9) 0.0572(4) Uani 1 1 d . . .
S2 S 0.16994(12) -0.05204(8) 0.98719(10) 0.0493(4) Uani 1 1 d . . .
O1 O 0.6351(3) 0.1819(2) 1.1751(2) 0.0394(8) Uani 1 1 d . . .
H1 H 0.571(3) 0.166(2) 1.130(3) 0.028(13) Uiso 1 1 d . . .
C1 C 0.4531(4) 0.0612(3) 0.6194(3) 0.0652(15) Uani 1 1 d . . .
H1B H 0.5019 0.0613 0.6948 0.078 Uiso 1 1 d R . .
H1C H 0.4063 0.0089 0.6053 0.078 Uiso 1 1 d R . .
H1D H 0.5145 0.0682 0.5662 0.078 Uiso 1 1 d R . .
C2 C 0.3552(4) 0.1297(3) 0.6067(3) 0.0419(12) Uani 1 1 d . . .
C3 C 0.3287(4) 0.1848(3) 0.6876(3) 0.0322(10) Uani 1 1 d . . .
C4 C 0.2255(4) 0.2428(3) 0.6454(4) 0.0397(12) Uani 1 1 d . . .
H4 H 0.185(3) 0.287(2) 0.696(3) 0.029(10) Uiso 1 1 d . . .
C5 C 0.1738(4) 0.2301(3) 0.5350(4) 0.0463(13) Uani 1 1 d . . .
C6 C 0.0639(4) 0.2796(3) 0.4643(4) 0.0650(15) Uani 1 1 d . . .
H6A H 0.0347 0.3231 0.5106 0.078 Uiso 1 1 d R . .
H6B H 0.0969 0.3044 0.4009 0.078 Uiso 1 1 d R . .
H6C H -0.0102 0.2433 0.4379 0.078 Uiso 1 1 d R . .
C7 C 0.3694(4) 0.0351(3) 1.1230(3) 0.0505(13) Uani 1 1 d . . .
H7A H 0.3455 -0.0089 1.1711 0.061 Uiso 1 1 d R . .
H7B H 0.3487 0.0884 1.1535 0.061 Uiso 1 1 d R . .
H7C H 0.4639 0.0323 1.1202 0.061 Uiso 1 1 d R . .
C8 C 0.2912(4) 0.0244(3) 1.0079(3) 0.0398(12) Uani 1 1 d . . .
C9 C 0.2971(4) 0.0674(3) 0.9092(3) 0.0344(11) Uani 1 1 d . . .
C10 C 0.2019(4) 0.0354(3) 0.8184(4) 0.0403(12) Uani 1 1 d . . .
H10 H 0.191(3) 0.0536(19) 0.747(2) 0.012(9) Uiso 1 1 d . . .
C11 C 0.1260(4) -0.0280(3) 0.8468(3) 0.0446(12) Uani 1 1 d . . .
C12 C 0.0183(4) -0.0759(3) 0.7729(4) 0.0570(14) Uani 1 1 d . . .
H12A H 0.0078 -0.0535 0.6976 0.068 Uiso 1 1 d R . .
H12B H 0.0436 -0.1339 0.7714 0.068 Uiso 1 1 d R . .
H12C H -0.0650 -0.0710 0.8020 0.068 Uiso 1 1 d R . .
C13 C 0.4009(4) 0.1838(3) 0.8033(3) 0.0309(10) Uani 1 1 d . . .
C14 C 0.3898(4) 0.1350(3) 0.8966(3) 0.0322(10) Uani 1 1 d . . .
C15 C 0.5508(4) 0.2241(3) 0.9479(3) 0.0346(11) Uani 1 1 d . . .
C16 C 0.6568(4) 0.2716(3) 1.0162(3) 0.0353(11) Uani 1 1 d . . .
C17 C 0.6944(4) 0.2472(3) 1.1299(3) 0.0376(11) Uani 1 1 d . . .
C18 C 0.7918(4) 0.2923(3) 1.2001(3) 0.0449(12) Uani 1 1 d . . .
H18A H 0.8149 0.2768 1.2781 0.054 Uiso 1 1 d R . .
C19 C 0.8554(4) 0.3589(3) 1.1584(4) 0.0546(14) Uani 1 1 d . . .
H19A H 0.9238 0.3889 1.2071 0.065 Uiso 1 1 d R . .
C20 C 0.8217(4) 0.3831(3) 1.0471(4) 0.0524(13) Uani 1 1 d . . .
H20A H 0.8653 0.4305 1.0190 0.063 Uiso 1 1 d R . .
C21 C 0.7246(4) 0.3389(3) 0.9760(3) 0.0405(12) Uani 1 1 d . . .
H21A H 0.7037 0.3549 0.8981 0.049 Uiso 1 1 d R . .
N1 N 0.5031(4) 0.2399(2) 0.8377(3) 0.0340(10) Uani 1 1 d . . .
H1A H 0.538(3) 0.269(2) 0.796(3) 0.017(12) Uiso 1 1 d . . .
N2 N 0.4851(3) 0.1624(2) 0.9862(2) 0.0334(9) Uani 1 1 d . . .


_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 C5 1.678(5) . ?
S1 C2 1.726(4) . ?
S2 C11 1.715(4) . ?
S2 C8 1.717(4) . ?
O1 C17 1.354(5) . ?
O1 H1 0.81(3) . ?
C1 C2 1.464(5) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9599 . ?
C1 H1D 0.9601 . ?
C2 C3 1.364(5) . ?
C3 C4 1.426(5) . ?
C3 C13 1.465(5) . ?
C4 C5 1.361(5) . ?
C4 H4 1.05(3) . ?
C5 C6 1.511(5) . ?
C6 H6A 0.9601 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9599 . ?
C7 C8 1.490(5) . ?
C7 H7A 0.9599 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.375(5) . ?
C9 C10 1.431(5) . ?
C9 C14 1.450(5) . ?
C10 C11 1.343(6) . ?
C10 H10 0.89(3) . ?
C11 C12 1.501(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9599 . ?
C12 H12C 0.9601 . ?
C13 N1 1.378(5) . ?
C13 C14 1.380(5) . ?
C14 N2 1.397(4) . ?
C15 N2 1.307(5) . ?
C15 N1 1.357(4) . ?
C15 C16 1.455(5) . ?
C16 C21 1.396(5) . ?
C16 C17 1.411(5) . ?
C17 C18 1.392(5) . ?
C18 C19 1.373(6) . ?
C18 H18A 0.9600 . ?
C19 C20 1.380(5) . ?
C19 H19A 0.9601 . ?
C20 C21 1.387(5) . ?
C20 H20A 0.9601 . ?
C21 H21A 0.9600 . ?
N1 H1A 0.80(3) . ?

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
C5 S1 C2 93.6(2) . . ?
C11 S2 C8 93.1(2) . . ?
C17 O1 H1 109(3) . . ?
C2 C1 H1B 109.8 . . ?
C2 C1 H1C 108.9 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1D 109.7 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
C3 C2 C1 127.4(4) . . ?
C3 C2 S1 109.9(3) . . ?
C1 C2 S1 122.6(3) . . ?
C2 C3 C4 112.2(4) . . ?
C2 C3 C13 122.8(4) . . ?
C4 C3 C13 125.0(4) . . ?
C5 C4 C3 113.4(4) . . ?
C5 C4 H4 122.3(18) . . ?
C3 C4 H4 124.0(18) . . ?
C4 C5 C6 127.3(4) . . ?
C4 C5 S1 110.9(3) . . ?
C6 C5 S1 121.9(3) . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 110.2 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.7 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.7 . . ?
H7A C7 H7B 109.2 . . ?
C8 C7 H7C 110.5 . . ?
H7A C7 H7C 109.2 . . ?
H7B C7 H7C 109.1 . . ?
C9 C8 C7 130.7(4) . . ?
C9 C8 S2 110.7(3) . . ?
C7 C8 S2 118.6(3) . . ?
C8 C9 C10 111.3(4) . . ?
C8 C9 C14 124.9(4) . . ?
C10 C9 C14 123.7(4) . . ?
C11 C10 C9 114.7(4) . . ?
C11 C10 H10 120(2) . . ?
C9 C10 H10 125(2) . . ?
C10 C11 C12 128.4(4) . . ?
C10 C11 S2 110.2(3) . . ?
C12 C11 S2 121.4(4) . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.8 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 105.8(3) . . ?
N1 C13 C3 121.1(4) . . ?
C14 C13 C3 133.0(4) . . ?
C13 C14 N2 108.3(4) . . ?
C13 C14 C9 129.5(4) . . ?
N2 C14 C9 122.1(3) . . ?
N2 C15 N1 111.0(4) . . ?
N2 C15 C16 124.1(4) . . ?
N1 C15 C16 124.9(4) . . ?
C21 C16 C17 118.0(4) . . ?
C21 C16 C15 124.2(4) . . ?
C17 C16 C15 117.7(4) . . ?
O1 C17 C18 118.0(4) . . ?
O1 C17 C16 121.9(4) . . ?
C18 C17 C16 120.1(4) . . ?
C19 C18 C17 120.4(4) . . ?
C19 C18 H18A 119.7 . . ?
C17 C18 H18A 119.9 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C19 C20 C21 119.8(4) . . ?
C19 C20 H20A 120.0 . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 C16 121.1(4) . . ?
C20 C21 H21A 119.4 . . ?
C16 C21 H21A 119.5 . . ?
C15 N1 C13 108.0(4) . . ?
C15 N1 H1A 126(2) . . ?
C13 N1 H1A 125(2) . . ?
C15 N2 C14 106.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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 1023277'
_audit_update_record             
;
2014-09-07 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 N2 O S2'
_chemical_formula_weight         456.60

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1   '
_symmetry_space_group_name_Hall  '-P 1   '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.5307(13)
_cell_length_b                   12.7677(14)
_cell_length_c                   18.229(2)
_cell_angle_alpha                103.512(2)
_cell_angle_beta                 92.109(2)
_cell_angle_gamma                111.527(2)
_cell_volume                     2405.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3743
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      23.89

_exptl_crystal_description       blocky
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.957
_exptl_absorpt_process_details   'SADABS, Bruker(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19604
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         26.00
_reflns_number_total             9357
_reflns_number_gt                4982
_reflns_threshold_expression     >2sigma(I)

_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  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1144P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9357
_refine_ls_number_parameters     577
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1162
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.2153
_refine_ls_wR_factor_gt          0.1687
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.010
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.62891(8) 1.02391(9) 0.20596(5) 0.0783(3) Uani 1 1 d . . .
S2 S 0.17194(12) 1.14579(17) 0.36931(8) 0.1379(6) Uani 1 1 d U . .
S3 S 0.52337(9) 0.32178(10) 1.13550(6) 0.0913(3) Uani 1 1 d U . .
S4 S 0.87576(9) 0.03622(9) 1.07445(5) 0.0758(3) Uani 1 1 d . . .
O1 O 0.1225(3) 0.7350(4) 0.50303(17) 0.1275(13) Uani 1 1 d . . .
H1A H 0.1581 0.7887 0.4815 0.191 Uiso 1 1 d R . .
O2 O 0.7365(3) 0.5268(3) 0.86428(19) 0.1081(9) Uani 1 1 d U . .
H2B H 0.7338 0.4929 0.8995 0.162 Uiso 1 1 d R . .
N1 N 0.2898(3) 0.8651(3) 0.44069(17) 0.0891(10) Uani 1 1 d . . .
N2 N 0.4518(2) 0.8252(3) 0.39939(15) 0.0757(8) Uani 1 1 d . . .
N3 N 0.7677(3) 0.3857(2) 0.93512(16) 0.0689(7) Uani 1 1 d . . .
N4 N 0.9067(2) 0.3048(2) 0.91012(13) 0.0569(6) Uani 1 1 d . . .
C1 C 0.1953(4) 0.6716(5) 0.5050(2) 0.1092(17) Uani 1 1 d . . .
C2 C 0.1488(5) 0.5809(6) 0.5392(3) 0.134(2) Uani 1 1 d . . .
H2A H 0.0750 0.5683 0.5611 0.161 Uiso 1 1 calc R . .
C3 C 0.2146(6) 0.5091(6) 0.5399(3) 0.145(3) Uani 1 1 d . . .
H3B H 0.1816 0.4441 0.5588 0.174 Uiso 1 1 calc R . .
C4 C 0.3252(5) 0.5337(5) 0.5134(3) 0.1253(18) Uani 1 1 d . . .
H4A H 0.3707 0.4874 0.5158 0.150 Uiso 1 1 calc R . .
C5 C 0.3734(5) 0.6288(5) 0.4821(3) 0.1135(16) Uani 1 1 d . . .
H5A H 0.4515 0.6453 0.4649 0.136 Uiso 1 1 calc R . .
C6 C 0.3082(4) 0.6985(4) 0.4761(2) 0.0906(13) Uani 1 1 d . . .
C7 C 0.3509(4) 0.7966(4) 0.4404(2) 0.0880(12) Uani 1 1 d . . .
C8 C 0.5326(3) 0.7659(3) 0.37673(18) 0.0741(10) Uani 1 1 d . . .
C9 C 0.6483(4) 0.7996(4) 0.4187(2) 0.0897(11) Uani 1 1 d . . .
H9A H 0.6734 0.8606 0.4629 0.108 Uiso 1 1 calc R . .
C10 C 0.7265(5) 0.7426(5) 0.3950(4) 0.1124(15) Uani 1 1 d . . .
H10A H 0.8039 0.7638 0.4236 0.135 Uiso 1 1 calc R . .
C11 C 0.6895(7) 0.6544(6) 0.3288(4) 0.1260(19) Uani 1 1 d . . .
H11A H 0.7435 0.6174 0.3122 0.151 Uiso 1 1 calc R . .
C12 C 0.5764(7) 0.6201(5) 0.2873(3) 0.128(2) Uani 1 1 d . . .
H12A H 0.5521 0.5591 0.2431 0.154 Uiso 1 1 calc R . .
C13 C 0.4969(5) 0.6763(4) 0.3108(2) 0.1019(14) Uani 1 1 d . . .
H13A H 0.4192 0.6535 0.2822 0.122 Uiso 1 1 calc R . .
C14 C 0.4501(3) 0.9181(3) 0.37310(18) 0.0714(9) Uani 1 1 d . . .
C15 C 0.3493(3) 0.9416(4) 0.3987(2) 0.0810(11) Uani 1 1 d . . .
C16 C 0.3742(4) 0.8907(4) 0.2045(2) 0.1160(17) Uani 1 1 d . . .
H16A H 0.3165 0.8562 0.2369 0.174 Uiso 1 1 calc R . .
H16B H 0.3746 0.8306 0.1616 0.174 Uiso 1 1 calc R . .
H16C H 0.3487 0.9452 0.1869 0.174 Uiso 1 1 calc R . .
C17 C 0.5034(3) 0.9530(3) 0.24811(18) 0.0711(9) Uani 1 1 d . . .
C18 C 0.5391(3) 0.9678(3) 0.32298(18) 0.0637(8) Uani 1 1 d . . .
C19 C 0.6696(3) 1.0366(3) 0.34537(19) 0.0697(9) Uani 1 1 d . . .
H19A H 0.7091 1.0540 0.3946 0.084 Uiso 1 1 calc R . .
C20 C 0.7318(3) 1.0749(3) 0.2890(2) 0.0670(8) Uani 1 1 d . . .
C21 C 0.8648(3) 1.1510(3) 0.2912(2) 0.0877(11) Uani 1 1 d . . .
H21A H 0.9085 1.1714 0.3415 0.132 Uiso 1 1 calc R . .
H21B H 0.8691 1.2208 0.2780 0.132 Uiso 1 1 calc R . .
H21C H 0.9033 1.1104 0.2554 0.132 Uiso 1 1 calc R . .
C22 C 0.0701(4) 0.9285(6) 0.3987(3) 0.157(3) Uani 1 1 d . . .
H22A H 0.0918 0.8663 0.4076 0.236 Uiso 1 1 calc R . .
H22B H 0.0083 0.8989 0.3543 0.236 Uiso 1 1 calc R . .
H22C H 0.0362 0.9595 0.4420 0.236 Uiso 1 1 calc R . .
C23 C 0.1847(4) 1.0227(5) 0.3865(3) 0.1185(12) Uani 1 1 d U . .
C24 C 0.3057(3) 1.0300(4) 0.38570(19) 0.0860(12) Uani 1 1 d . . .
C25 C 0.3847(4) 1.1354(4) 0.3705(2) 0.0902(12) Uani 1 1 d . . .
H25A H 0.4701 1.1541 0.3678 0.108 Uiso 1 1 calc R . .
C26 C 0.3269(4) 1.2065(5) 0.3603(2) 0.0993(13) Uani 1 1 d . . .
C27 C 0.3789(5) 1.3213(5) 0.3419(3) 0.1326(19) Uani 1 1 d . . .
H27A H 0.4672 1.3426 0.3387 0.199 Uiso 1 1 calc R . .
H27B H 0.3668 1.3797 0.3812 0.199 Uiso 1 1 calc R . .
H27C H 0.3362 1.3156 0.2941 0.199 Uiso 1 1 calc R . .
C28 C 0.8095(4) 0.4989(3) 0.8160(2) 0.0820(9) Uani 1 1 d U . .
C29 C 0.8266(4) 0.5458(4) 0.7524(3) 0.1053(13) Uani 1 1 d U . .
H29A H 0.7902 0.5985 0.7480 0.126 Uiso 1 1 calc R . .
C30 C 0.8929(4) 0.5173(4) 0.6985(3) 0.1011(13) Uani 1 1 d U . .
H30A H 0.9031 0.5504 0.6576 0.121 Uiso 1 1 calc R . .
C31 C 0.9446(4) 0.4405(4) 0.7038(2) 0.1006(13) Uani 1 1 d . . .
H31A H 0.9890 0.4194 0.6653 0.121 Uiso 1 1 calc R . .
C32 C 0.9345(4) 0.3923(4) 0.7636(2) 0.0925(12) Uani 1 1 d . . .
H32A H 0.9714 0.3391 0.7653 0.111 Uiso 1 1 calc R . .
C33 C 0.8680(3) 0.4226(3) 0.8232(2) 0.0695(9) Uani 1 1 d . . .
C34 C 0.8510(3) 0.3724(3) 0.88812(18) 0.0635(8) Uani 1 1 d . . .
C35 C 1.0068(3) 0.2760(3) 0.87938(17) 0.0575(7) Uani 1 1 d . . .
C36 C 1.1267(3) 0.3591(3) 0.8965(2) 0.0811(10) Uani 1 1 d . . .
H36A H 1.1425 0.4330 0.9279 0.097 Uiso 1 1 calc R . .
C37 C 1.2255(4) 0.3324(5) 0.8664(3) 0.0976(13) Uani 1 1 d . . .
H37A H 1.3070 0.3888 0.8758 0.117 Uiso 1 1 calc R . .
C38 C 1.1997(5) 0.2225(6) 0.8232(3) 0.1043(15) Uani 1 1 d . . .
H38A H 1.2653 0.2030 0.8046 0.125 Uiso 1 1 calc R . .
C39 C 1.0808(4) 0.1402(4) 0.8064(2) 0.0916(12) Uani 1 1 d . . .
H39A H 1.0650 0.0659 0.7755 0.110 Uiso 1 1 calc R . .
C40 C 0.9840(3) 0.1671(3) 0.8351(2) 0.0750(9) Uani 1 1 d . . .
H40A H 0.9024 0.1107 0.8241 0.090 Uiso 1 1 calc R . .
C41 C 0.7697(3) 0.3255(3) 0.98899(17) 0.0605(8) Uani 1 1 d . . .
C42 C 0.8542(3) 0.2738(3) 0.97378(17) 0.0593(7) Uani 1 1 d . . .
C43 C 0.4892(4) 0.3092(5) 0.9803(3) 0.1170(16) Uani 1 1 d . . .
H43A H 0.5328 0.3091 0.9365 0.175 Uiso 1 1 calc R . .
H43B H 0.4636 0.3742 0.9904 0.175 Uiso 1 1 calc R . .
H43C H 0.4163 0.2378 0.9709 0.175 Uiso 1 1 calc R . .
C44 C 0.5747(3) 0.3196(3) 1.0478(2) 0.0759(9) Uani 1 1 d U . .
C45 C 0.6946(3) 0.3244(3) 1.05119(18) 0.0626(8) Uani 1 1 d . . .
C46 C 0.7437(3) 0.3325(3) 1.12770(19) 0.0695(9) Uani 1 1 d . . .
H46A H 0.8249 0.3378 1.1404 0.083 Uiso 1 1 calc R . .
C47 C 0.6633(3) 0.3318(3) 1.1781(2) 0.0764(9) Uani 1 1 d . . .
C48 C 0.6838(4) 0.3396(4) 1.2621(2) 0.1033(13) Uani 1 1 d . . .
H48A H 0.7675 0.3451 1.2756 0.155 Uiso 1 1 calc R . .
H48B H 0.6239 0.2710 1.2724 0.155 Uiso 1 1 calc R . .
H48C H 0.6730 0.4075 1.2914 0.155 Uiso 1 1 calc R . .
C49 C 0.6666(3) 0.0409(3) 0.9975(2) 0.0828(10) Uani 1 1 d . . .
H49A H 0.6413 0.0857 0.9694 0.124 Uiso 1 1 calc R . .
H49B H 0.6227 0.0364 1.0411 0.124 Uiso 1 1 calc R . .
H49C H 0.6467 -0.0363 0.9655 0.124 Uiso 1 1 calc R . .
C50 C 0.8037(3) 0.0981(3) 1.02277(17) 0.0624(8) Uani 1 1 d . . .
C51 C 0.8897(3) 0.1985(3) 1.01214(17) 0.0583(7) Uani 1 1 d . . .
C52 C 1.0128(3) 0.2230(3) 1.04548(18) 0.0676(8) Uani 1 1 d . . .
H52A H 1.0822 0.2876 1.0425 0.081 Uiso 1 1 calc R . .
C53 C 1.0212(3) 0.1448(3) 1.08203(19) 0.0734(9) Uani 1 1 d . . .
C54 C 1.1344(4) 0.1439(4) 1.1247(2) 0.0969(12) Uani 1 1 d . . .
H54A H 1.2073 0.2105 1.1228 0.145 Uiso 1 1 calc R . .
H54B H 1.1467 0.0737 1.1019 0.145 Uiso 1 1 calc R . .
H54C H 1.1217 0.1472 1.1768 0.145 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
S1 C17 1.718(3) . ?
S1 C20 1.721(3) . ?
S2 C26 1.699(5) . ?
S2 C23 1.729(6) . ?
S3 C47 1.713(4) . ?
S3 C44 1.722(4) . ?
S4 C53 1.715(4) . ?
S4 C50 1.724(3) . ?
O1 C1 1.368(6) . ?
O1 H1A 0.8500 . ?
O2 C28 1.319(5) . ?
O2 H2B 0.8499 . ?
N1 C7 1.309(5) . ?
N1 C15 1.381(5) . ?
N2 C7 1.388(4) . ?
N2 C14 1.386(5) . ?
N2 C8 1.418(5) . ?
N3 C34 1.341(4) . ?
N3 C41 1.386(4) . ?
N4 C34 1.366(4) . ?
N4 C42 1.400(4) . ?
N4 C35 1.430(4) . ?
C1 C6 1.377(5) . ?
C1 C2 1.386(7) . ?
C2 C3 1.390(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.334(7) . ?
C3 H3B 0.9300 . ?
C4 C5 1.399(6) . ?
C4 H4A 0.9300 . ?
C5 C6 1.379(6) . ?
C5 H5A 0.9300 . ?
C6 C7 1.479(6) . ?
C8 C9 1.378(5) . ?
C8 C13 1.378(5) . ?
C9 C10 1.375(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.372(8) . ?
C10 H10A 0.9300 . ?
C11 C12 1.349(8) . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(7) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 C15 1.375(5) . ?
C14 C18 1.467(4) . ?
C15 C24 1.454(6) . ?
C16 C17 1.493(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.360(4) . ?
C18 C19 1.420(4) . ?
C19 C20 1.357(4) . ?
C19 H19A 0.9300 . ?
C20 C21 1.477(4) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.491(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.364(5) . ?
C24 C25 1.418(6) . ?
C25 C26 1.348(6) . ?
C25 H25A 0.9300 . ?
C26 C27 1.489(7) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C33 1.398(5) . ?
C28 C29 1.413(5) . ?
C29 C30 1.333(6) . ?
C29 H29A 0.9300 . ?
C30 C31 1.341(6) . ?
C30 H30A 0.9300 . ?
C31 C32 1.360(5) . ?
C31 H31A 0.9300 . ?
C32 C33 1.414(5) . ?
C32 H32A 0.9300 . ?
C33 C34 1.460(4) . ?
C35 C40 1.359(5) . ?
C35 C36 1.368(4) . ?
C36 C37 1.399(6) . ?
C36 H36A 0.9300 . ?
C37 C38 1.356(7) . ?
C37 H37A 0.9300 . ?
C38 C39 1.356(6) . ?
C38 H38A 0.9300 . ?
C39 C40 1.370(5) . ?
C39 H39A 0.9300 . ?
C40 H40A 0.9300 . ?
C41 C42 1.367(4) . ?
C41 C45 1.451(4) . ?
C42 C51 1.470(4) . ?
C43 C44 1.498(5) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 C45 1.359(4) . ?
C45 C46 1.452(5) . ?
C46 C47 1.328(4) . ?
C46 H46A 0.9300 . ?
C47 C48 1.515(5) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.480(4) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 C51 1.364(4) . ?
C51 C52 1.415(4) . ?
C52 C53 1.352(5) . ?
C52 H52A 0.9300 . ?
C53 C54 1.500(5) . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 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
C17 S1 C20 92.98(16) . . ?
C26 S2 C23 93.0(2) . . ?
C47 S3 C44 93.28(17) . . ?
C53 S4 C50 92.91(16) . . ?
C1 O1 H1A 109.1 . . ?
C28 O2 H2B 109.0 . . ?
C7 N1 C15 107.2(3) . . ?
C7 N2 C14 106.1(3) . . ?
C7 N2 C8 129.9(4) . . ?
C14 N2 C8 123.5(3) . . ?
C34 N3 C41 107.7(3) . . ?
C34 N4 C42 107.4(2) . . ?
C34 N4 C35 128.1(3) . . ?
C42 N4 C35 124.4(2) . . ?
O1 C1 C6 121.7(5) . . ?
O1 C1 C2 115.5(5) . . ?
C6 C1 C2 122.8(6) . . ?
C1 C2 C3 118.7(6) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 H2A 120.7 . . ?
C4 C3 C2 119.9(6) . . ?
C4 C3 H3B 120.1 . . ?
C2 C3 H3B 120.1 . . ?
C3 C4 C5 120.5(6) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 121.7(5) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C1 C6 C5 116.2(5) . . ?
C1 C6 C7 119.4(5) . . ?
C5 C6 C7 124.4(4) . . ?
N1 C7 N2 111.0(4) . . ?
N1 C7 C6 122.0(4) . . ?
N2 C7 C6 126.9(5) . . ?
C9 C8 C13 119.6(4) . . ?
C9 C8 N2 120.6(3) . . ?
C13 C8 N2 119.7(4) . . ?
C10 C9 C8 119.8(4) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C11 C10 C9 119.5(5) . . ?
C11 C10 H10A 120.2 . . ?
C9 C10 H10A 120.2 . . ?
C12 C11 C10 121.3(5) . . ?
C12 C11 H11A 119.4 . . ?
C10 C11 H11A 119.4 . . ?
C11 C12 C13 119.6(5) . . ?
C11 C12 H12A 120.2 . . ?
C13 C12 H12A 120.2 . . ?
C8 C13 C12 120.1(5) . . ?
C8 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 N2 106.7(3) . . ?
C15 C14 C18 131.4(4) . . ?
N2 C14 C18 121.7(3) . . ?
C14 C15 N1 109.0(4) . . ?
C14 C15 C24 128.4(4) . . ?
N1 C15 C24 122.6(3) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C17 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C16 128.0(3) . . ?
C18 C17 S1 110.9(2) . . ?
C16 C17 S1 121.0(3) . . ?
C17 C18 C19 112.1(3) . . ?
C17 C18 C14 122.4(3) . . ?
C19 C18 C14 125.5(3) . . ?
C20 C19 C18 114.5(3) . . ?
C20 C19 H19A 122.8 . . ?
C18 C19 H19A 122.8 . . ?
C19 C20 C21 130.0(3) . . ?
C19 C20 S1 109.6(2) . . ?
C21 C20 S1 120.4(3) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 H22A 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C23 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C22 130.5(6) . . ?
C24 C23 S2 110.5(4) . . ?
C22 C23 S2 119.0(4) . . ?
C23 C24 C25 111.4(5) . . ?
C23 C24 C15 124.8(4) . . ?
C25 C24 C15 123.8(3) . . ?
C26 C25 C24 115.1(4) . . ?
C26 C25 H25A 122.5 . . ?
C24 C25 H25A 122.5 . . ?
C25 C26 C27 129.7(4) . . ?
C25 C26 S2 110.0(4) . . ?
C27 C26 S2 120.2(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O2 C28 C33 123.5(3) . . ?
O2 C28 C29 118.3(4) . . ?
C33 C28 C29 118.2(4) . . ?
C30 C29 C28 122.4(4) . . ?
C30 C29 H29A 118.8 . . ?
C28 C29 H29A 118.8 . . ?
C29 C30 C31 119.3(4) . . ?
C29 C30 H30A 120.4 . . ?
C31 C30 H30A 120.4 . . ?
C30 C31 C32 122.2(5) . . ?
C30 C31 H31A 118.9 . . ?
C32 C31 H31A 118.9 . . ?
C31 C32 C33 120.4(4) . . ?
C31 C32 H32A 119.8 . . ?
C33 C32 H32A 119.8 . . ?
C28 C33 C32 117.4(3) . . ?
C28 C33 C34 119.2(3) . . ?
C32 C33 C34 123.2(3) . . ?
N3 C34 N4 109.6(3) . . ?
N3 C34 C33 121.0(3) . . ?
N4 C34 C33 129.4(3) . . ?
C40 C35 C36 120.3(3) . . ?
C40 C35 N4 120.7(3) . . ?
C36 C35 N4 119.0(3) . . ?
C35 C36 C37 119.6(4) . . ?
C35 C36 H36A 120.2 . . ?
C37 C36 H36A 120.2 . . ?
C38 C37 C36 118.5(4) . . ?
C38 C37 H37A 120.7 . . ?
C36 C37 H37A 120.7 . . ?
C39 C38 C37 121.7(4) . . ?
C39 C38 H38A 119.2 . . ?
C37 C38 H38A 119.2 . . ?
C38 C39 C40 119.6(4) . . ?
C38 C39 H39A 120.2 . . ?
C40 C39 H39A 120.2 . . ?
C35 C40 C39 120.2(4) . . ?
C35 C40 H40A 119.9 . . ?
C39 C40 H40A 119.9 . . ?
C42 C41 N3 108.6(3) . . ?
C42 C41 C45 128.3(3) . . ?
N3 C41 C45 123.0(3) . . ?
C41 C42 N4 106.7(3) . . ?
C41 C42 C51 130.5(3) . . ?
N4 C42 C51 122.8(3) . . ?
C44 C43 H43A 109.5 . . ?
C44 C43 H43B 109.5 . . ?
H43A C43 H43B 109.5 . . ?
C44 C43 H43C 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C45 C44 C43 128.7(4) . . ?
C45 C44 S3 110.6(3) . . ?
C43 C44 S3 120.7(3) . . ?
C44 C45 C41 126.5(3) . . ?
C44 C45 C46 111.2(3) . . ?
C41 C45 C46 122.2(3) . . ?
C47 C46 C45 114.6(3) . . ?
C47 C46 H46A 122.7 . . ?
C45 C46 H46A 122.7 . . ?
C46 C47 C48 128.3(4) . . ?
C46 C47 S3 110.3(3) . . ?
C48 C47 S3 121.4(3) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 H49A 109.5 . . ?
C50 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C50 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C51 C50 C49 129.9(3) . . ?
C51 C50 S4 110.5(2) . . ?
C49 C50 S4 119.7(2) . . ?
C50 C51 C52 112.2(3) . . ?
C50 C51 C42 122.6(3) . . ?
C52 C51 C42 125.1(3) . . ?
C53 C52 C51 114.6(3) . . ?
C53 C52 H52A 122.7 . . ?
C51 C52 H52A 122.7 . . ?
C52 C53 C54 129.3(3) . . ?
C52 C53 S4 109.9(2) . . ?
C54 C53 S4 120.8(3) . . ?
C53 C54 H54A 109.5 . . ?
C53 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C53 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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 1023278'
_audit_update_record             
;
2014-09-07 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C45 H39 F4 Ir N4 O3 S2'
_chemical_formula_weight         1016.12

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   16.885(6)
_cell_length_b                   11.685(4)
_cell_length_c                   21.931(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.950(6)
_cell_angle_gamma                90.00
_cell_volume                     4304(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4907
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.36

_exptl_crystal_description       blocky
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2024
_exptl_absorpt_coefficient_mu    3.261
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.739
_exptl_absorpt_correction_T_max  0.822
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24428
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         25.00
_reflns_number_total             7465
_reflns_number_gt                6012
_reflns_threshold_expression     >2sigma(I)

_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  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1841P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7465
_refine_ls_number_parameters     532
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0757
_refine_ls_wR_factor_ref         0.2423
_refine_ls_wR_factor_gt          0.2170
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.510370(19) 0.92171(3) 0.283998(15) 0.0290(2) Uani 1 1 d . . .
S1 S 0.88368(18) 1.1206(3) 0.52859(17) 0.0641(9) Uani 1 1 d . . .
S2 S 0.6420(2) 0.7137(2) 0.50510(14) 0.0539(7) Uani 1 1 d . . .
O1 O 0.5573(4) 1.0347(6) 0.2185(3) 0.0409(16) Uani 1 1 d . . .
O2 O 0.6107(6) 0.9514(11) 0.1189(4) 0.083(3) Uani 1 1 d . . .
H2D H 0.5915 0.9786 0.1502 0.099 Uiso 1 1 d R . .
O3 O 0.7403(6) 0.3814(8) 0.3922(4) 0.063(2) Uani 1 1 d . . .
H3B H 0.7754 0.4172 0.3745 0.076 Uiso 1 1 d R . .
N1 N 0.5829(4) 1.0274(7) 0.3501(3) 0.0293(16) Uani 1 1 d . . .
N2 N 0.6691(4) 1.1646(6) 0.3742(3) 0.0301(16) Uani 1 1 d . . .
H2A H 0.6946 1.2280 0.3724 0.036 Uiso 1 1 calc R . .
N3 N 0.6047(5) 0.8140(7) 0.2871(4) 0.0366(18) Uani 1 1 d . . .
N4 N 0.4105(5) 1.0210(7) 0.2795(4) 0.0353(18) Uani 1 1 d . . .
C1 C 0.4702(6) 0.7972(8) 0.3360(4) 0.034(2) Uani 1 1 d . . .
C2 C 0.3974(7) 0.7892(9) 0.3568(4) 0.042(2) Uani 1 1 d . . .
H31A H 0.3620 0.8501 0.3513 0.051 Uiso 1 1 calc R . .
C3 C 0.3759(6) 0.6917(10) 0.3861(5) 0.045(3) Uani 1 1 d . . .
C4 C 0.4244(7) 0.6009(10) 0.3953(6) 0.050(3) Uani 1 1 d . . .
H29A H 0.4090 0.5365 0.4160 0.060 Uiso 1 1 calc R . .
C5 C 0.4965(7) 0.6063(9) 0.3736(5) 0.046(3) Uani 1 1 d . . .
C6 C 0.5228(6) 0.6996(8) 0.3429(4) 0.037(2) Uani 1 1 d . . .
C7 C 0.5983(6) 0.7112(9) 0.3165(4) 0.037(2) Uani 1 1 d . . .
C8 C 0.6615(7) 0.6343(9) 0.3195(6) 0.050(3) Uani 1 1 d . . .
H25A H 0.6572 0.5644 0.3391 0.060 Uiso 1 1 calc R . .
C9 C 0.7310(8) 0.6603(11) 0.2935(6) 0.064(3) Uani 1 1 d . . .
H24A H 0.7728 0.6083 0.2944 0.077 Uiso 1 1 calc R . .
C10 C 0.7353(7) 0.7622(11) 0.2672(6) 0.059(3) Uani 1 1 d . . .
H23A H 0.7822 0.7829 0.2514 0.070 Uiso 1 1 calc R . .
C11 C 0.6714(6) 0.8398(10) 0.2625(5) 0.044(2) Uani 1 1 d . . .
H22A H 0.6757 0.9092 0.2423 0.053 Uiso 1 1 calc R . .
C12 C 0.4454(6) 0.8503(8) 0.2139(5) 0.040(2) Uani 1 1 d . . .
C13 C 0.4677(6) 0.7539(10) 0.1801(5) 0.045(3) Uani 1 1 d . . .
H42A H 0.5142 0.7132 0.1916 0.054 Uiso 1 1 calc R . .
C14 C 0.4146(9) 0.7219(12) 0.1267(6) 0.066(4) Uani 1 1 d . . .
C15 C 0.3495(9) 0.7763(16) 0.1091(7) 0.084(5) Uani 1 1 d . . .
H40A H 0.3172 0.7520 0.0746 0.101 Uiso 1 1 calc R . .
C16 C 0.3275(7) 0.8721(13) 0.1422(6) 0.062(3) Uani 1 1 d . . .
C17 C 0.3751(7) 0.9109(8) 0.1932(6) 0.043(3) Uani 1 1 d . . .
C18 C 0.3555(6) 1.0052(9) 0.2331(5) 0.042(2) Uani 1 1 d . . .
C19 C 0.2878(9) 1.0749(10) 0.2255(8) 0.068(4) Uani 1 1 d . . .
H36A H 0.2500 1.0650 0.1920 0.082 Uiso 1 1 calc R . .
C20 C 0.2784(9) 1.1574(13) 0.2680(7) 0.074(4) Uani 1 1 d . . .
H35A H 0.2331 1.2033 0.2635 0.088 Uiso 1 1 calc R . .
C21 C 0.3326(7) 1.1738(12) 0.3160(6) 0.059(3) Uani 1 1 d . . .
H34A H 0.3260 1.2308 0.3447 0.071 Uiso 1 1 calc R . .
C22 C 0.3984(7) 1.1037(10) 0.3216(6) 0.047(3) Uani 1 1 d . . .
H33A H 0.4361 1.1130 0.3553 0.056 Uiso 1 1 calc R . .
C23 C 0.8608(7) 1.1323(14) 0.4016(6) 0.068(4) Uani 1 1 d . . .
H1A H 0.8203 1.1285 0.3676 0.101 Uiso 1 1 calc R . .
H1B H 0.8994 1.0731 0.3977 0.101 Uiso 1 1 calc R . .
H1C H 0.8865 1.2056 0.4019 0.101 Uiso 1 1 calc R . .
C24 C 0.8245(7) 1.1165(11) 0.4592(5) 0.050(3) Uani 1 1 d . . .
C25 C 0.7490(8) 1.0908(9) 0.4689(5) 0.037(2) Uani 1 1 d . . .
C26 C 0.7375(8) 1.0737(9) 0.5315(5) 0.046(3) Uani 1 1 d . . .
H4A H 0.6887 1.0557 0.5452 0.055 Uiso 1 1 calc R . .
C27 C 0.8060(9) 1.0866(11) 0.5692(6) 0.058(3) Uani 1 1 d . . .
C28 C 0.8157(11) 1.0776(15) 0.6388(8) 0.089(6) Uani 1 1 d . . .
H6A H 0.7655 1.0579 0.6529 0.133 Uiso 1 1 calc R . .
H6B H 0.8334 1.1498 0.6561 0.133 Uiso 1 1 calc R . .
H6C H 0.8542 1.0196 0.6513 0.133 Uiso 1 1 calc R . .
C29 C 0.7591(6) 0.8088(11) 0.4400(5) 0.052(3) Uani 1 1 d . . .
H7A H 0.7684 0.8706 0.4128 0.078 Uiso 1 1 calc R . .
H7B H 0.7672 0.7372 0.4201 0.078 Uiso 1 1 calc R . .
H7C H 0.7954 0.8147 0.4765 0.078 Uiso 1 1 calc R . .
C30 C 0.6760(7) 0.8149(10) 0.4563(5) 0.045(3) Uani 1 1 d . . .
C31 C 0.6180(6) 0.8933(8) 0.4400(4) 0.034(2) Uani 1 1 d . . .
C32 C 0.5484(6) 0.8701(9) 0.4667(4) 0.039(2) Uani 1 1 d . . .
H10A H 0.5033 0.9158 0.4593 0.047 Uiso 1 1 calc R . .
C33 C 0.5498(7) 0.7781(9) 0.5039(5) 0.046(3) Uani 1 1 d . . .
C34 C 0.4877(10) 0.7295(13) 0.5393(7) 0.078(4) Uani 1 1 d . . .
H12A H 0.4405 0.7758 0.5333 0.117 Uiso 1 1 calc R . .
H12B H 0.5068 0.7282 0.5821 0.117 Uiso 1 1 calc R . .
H12C H 0.4754 0.6529 0.5256 0.117 Uiso 1 1 calc R . .
C35 C 0.6843(7) 1.0800(7) 0.4183(4) 0.035(2) Uani 1 1 d . . .
C36 C 0.6317(5) 0.9949(8) 0.4048(4) 0.0295(19) Uani 1 1 d . . .
C37 C 0.6075(6) 1.1297(8) 0.3348(4) 0.032(2) Uani 1 1 d . . .
C38 C 0.5771(6) 1.1977(8) 0.2826(4) 0.035(2) Uani 1 1 d . . .
C39 C 0.5536(5) 1.1479(8) 0.2257(4) 0.033(2) Uani 1 1 d . . .
C40 C 0.5303(7) 1.2188(10) 0.1752(5) 0.049(3) Uani 1 1 d . . .
H18A H 0.5149 1.1863 0.1371 0.059 Uiso 1 1 calc R . .
C41 C 0.5302(8) 1.3349(11) 0.1818(5) 0.059(3) Uani 1 1 d . . .
H19A H 0.5174 1.3811 0.1476 0.071 Uiso 1 1 calc R . .
C42 C 0.5488(8) 1.3846(11) 0.2385(6) 0.060(3) Uani 1 1 d . . .
H20A H 0.5459 1.4636 0.2430 0.072 Uiso 1 1 calc R . .
C43 C 0.5714(6) 1.3171(9) 0.2882(5) 0.044(2) Uani 1 1 d . . .
H21A H 0.5833 1.3509 0.3264 0.053 Uiso 1 1 calc R . .
C44 C 0.5544(13) 0.9525(18) 0.0697(7) 0.105(6) Uani 1 1 d . . .
H44C H 0.5238 0.8834 0.0706 0.125 Uiso 1 1 d R . .
H44A H 0.5779 0.9541 0.0317 0.125 Uiso 1 1 d R . .
H44B H 0.5186 1.0160 0.0713 0.125 Uiso 1 1 d R . .
C45 C 0.7347(12) 0.4136(12) 0.4555(8) 0.073(5) Uani 1 1 d . . .
H45C H 0.6834 0.4496 0.4540 0.088 Uiso 1 1 d R . .
H45A H 0.7710 0.4718 0.4719 0.088 Uiso 1 1 d R . .
H45B H 0.7313 0.3509 0.4834 0.088 Uiso 1 1 d R . .
F1 F 0.5472(5) 0.5169(6) 0.3845(4) 0.077(2) Uani 1 1 d . . .
F2 F 0.3024(4) 0.6876(7) 0.4078(3) 0.0662(19) Uani 1 1 d . . .
F3 F 0.2617(6) 0.9250(8) 0.1228(5) 0.096(3) Uani 1 1 d . . .
F4 F 0.4369(5) 0.6287(9) 0.0970(4) 0.095(3) Uani 1 1 d . . .


_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 C12 1.978(10) . ?
Ir1 C1 2.009(9) . ?
Ir1 N3 2.026(8) . ?
Ir1 N4 2.042(8) . ?
Ir1 O1 2.162(7) . ?
Ir1 N1 2.181(7) . ?
S1 C27 1.707(16) . ?
S1 C24 1.732(12) . ?
S2 C33 1.727(12) . ?
S2 C30 1.732(11) . ?
O1 C39 1.334(13) . ?
O2 C44 1.362(18) . ?
O2 H2D 0.8499 . ?
O3 C45 1.452(19) . ?
O3 H3B 0.8501 . ?
N1 C37 1.321(12) . ?
N1 C36 1.433(11) . ?
N2 C37 1.345(12) . ?
N2 C35 1.387(12) . ?
N2 H2A 0.8600 . ?
N3 C11 1.333(13) . ?
N3 C7 1.373(13) . ?
N4 C18 1.317(12) . ?
N4 C22 1.366(14) . ?
C1 C2 1.358(14) . ?
C1 C6 1.443(14) . ?
C2 C3 1.375(15) . ?
C2 H31A 0.9300 . ?
C3 C4 1.343(17) . ?
C3 F2 1.375(12) . ?
C4 C5 1.354(17) . ?
C4 H29A 0.9300 . ?
C5 F1 1.355(13) . ?
C5 C6 1.378(15) . ?
C6 C7 1.461(15) . ?
C7 C8 1.392(14) . ?
C8 C9 1.389(18) . ?
C8 H25A 0.9300 . ?
C9 C10 1.328(18) . ?
C9 H24A 0.9300 . ?
C10 C11 1.404(16) . ?
C10 H23A 0.9300 . ?
C11 H22A 0.9300 . ?
C12 C17 1.417(15) . ?
C12 C13 1.422(14) . ?
C13 C14 1.447(17) . ?
C13 H42A 0.9300 . ?
C14 C15 1.29(2) . ?
C14 F4 1.342(14) . ?
C15 C16 1.40(2) . ?
C15 H40A 0.9300 . ?
C16 F3 1.304(15) . ?
C16 C17 1.384(17) . ?
C17 C18 1.466(15) . ?
C18 C19 1.399(16) . ?
C19 C20 1.363(19) . ?
C19 H36A 0.9300 . ?
C20 C21 1.335(18) . ?
C20 H35A 0.9300 . ?
C21 C22 1.377(16) . ?
C21 H34A 0.9300 . ?
C22 H33A 0.9300 . ?
C23 C24 1.474(17) . ?
C23 H1A 0.9600 . ?
C23 H1B 0.9600 . ?
C23 H1C 0.9600 . ?
C24 C25 1.348(17) . ?
C25 C26 1.420(16) . ?
C25 C35 1.481(16) . ?
C26 C27 1.359(19) . ?
C26 H4A 0.9300 . ?
C27 C28 1.52(2) . ?
C28 H6A 0.9600 . ?
C28 H6B 0.9600 . ?
C28 H6C 0.9600 . ?
C29 C30 1.486(16) . ?
C29 H7A 0.9600 . ?
C29 H7B 0.9600 . ?
C29 H7C 0.9600 . ?
C30 C31 1.361(15) . ?
C31 C32 1.393(14) . ?
C31 C36 1.448(13) . ?
C32 C33 1.348(14) . ?
C32 H10A 0.9300 . ?
C33 C34 1.482(16) . ?
C34 H12A 0.9600 . ?
C34 H12B 0.9600 . ?
C34 H12C 0.9600 . ?
C35 C36 1.346(13) . ?
C37 C38 1.444(13) . ?
C38 C39 1.396(14) . ?
C38 C43 1.405(14) . ?
C39 C40 1.406(14) . ?
C40 C41 1.365(17) . ?
C40 H18A 0.9300 . ?
C41 C42 1.380(18) . ?
C41 H19A 0.9300 . ?
C42 C43 1.366(16) . ?
C42 H20A 0.9300 . ?
C43 H21A 0.9300 . ?
C44 H44C 0.9599 . ?
C44 H44A 0.9599 . ?
C44 H44B 0.9600 . ?
C45 H45C 0.9600 . ?
C45 H45A 0.9601 . ?
C45 H45B 0.9601 . ?

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
C12 Ir1 C1 86.7(4) . . ?
C12 Ir1 N3 97.8(4) . . ?
C1 Ir1 N3 80.9(4) . . ?
C12 Ir1 N4 79.2(4) . . ?
C1 Ir1 N4 96.5(4) . . ?
N3 Ir1 N4 176.2(3) . . ?
C12 Ir1 O1 87.3(4) . . ?
C1 Ir1 O1 171.1(3) . . ?
N3 Ir1 O1 93.5(3) . . ?
N4 Ir1 O1 88.8(3) . . ?
C12 Ir1 N1 169.5(4) . . ?
C1 Ir1 N1 103.4(3) . . ?
N3 Ir1 N1 86.8(3) . . ?
N4 Ir1 N1 96.6(3) . . ?
O1 Ir1 N1 83.0(3) . . ?
C27 S1 C24 92.7(6) . . ?
C33 S2 C30 92.8(5) . . ?
C39 O1 Ir1 120.1(5) . . ?
C44 O2 H2D 110.0 . . ?
C45 O3 H3B 115.2 . . ?
C37 N1 C36 106.5(7) . . ?
C37 N1 Ir1 120.9(6) . . ?
C36 N1 Ir1 129.8(6) . . ?
C37 N2 C35 107.8(8) . . ?
C37 N2 H2A 126.1 . . ?
C35 N2 H2A 126.1 . . ?
C11 N3 C7 120.0(9) . . ?
C11 N3 Ir1 122.7(7) . . ?
C7 N3 Ir1 117.3(6) . . ?
C18 N4 C22 118.6(9) . . ?
C18 N4 Ir1 118.0(7) . . ?
C22 N4 Ir1 123.3(7) . . ?
C2 C1 C6 118.5(9) . . ?
C2 C1 Ir1 127.7(8) . . ?
C6 C1 Ir1 113.1(7) . . ?
C1 C2 C3 120.4(10) . . ?
C1 C2 H31A 119.8 . . ?
C3 C2 H31A 119.8 . . ?
C4 C3 F2 118.6(10) . . ?
C4 C3 C2 122.5(10) . . ?
F2 C3 C2 118.8(10) . . ?
C3 C4 C5 117.9(11) . . ?
C3 C4 H29A 121.1 . . ?
C5 C4 H29A 121.1 . . ?
C4 C5 F1 118.4(11) . . ?
C4 C5 C6 123.7(11) . . ?
F1 C5 C6 117.8(10) . . ?
C5 C6 C1 116.9(10) . . ?
C5 C6 C7 127.2(9) . . ?
C1 C6 C7 115.9(9) . . ?
N3 C7 C8 119.3(10) . . ?
N3 C7 C6 112.5(9) . . ?
C8 C7 C6 128.2(10) . . ?
C9 C8 C7 121.0(11) . . ?
C9 C8 H25A 119.5 . . ?
C7 C8 H25A 119.5 . . ?
C10 C9 C8 117.4(11) . . ?
C10 C9 H24A 121.3 . . ?
C8 C9 H24A 121.3 . . ?
C9 C10 C11 122.4(12) . . ?
C9 C10 H23A 118.8 . . ?
C11 C10 H23A 118.8 . . ?
N3 C11 C10 119.9(11) . . ?
N3 C11 H22A 120.1 . . ?
C10 C11 H22A 120.1 . . ?
C17 C12 C13 119.2(10) . . ?
C17 C12 Ir1 114.7(7) . . ?
C13 C12 Ir1 125.8(8) . . ?
C12 C13 C14 116.8(11) . . ?
C12 C13 H42A 121.6 . . ?
C14 C13 H42A 121.6 . . ?
C15 C14 F4 121.7(12) . . ?
C15 C14 C13 123.4(12) . . ?
F4 C14 C13 114.9(13) . . ?
C14 C15 C16 119.9(12) . . ?
C14 C15 H40A 120.1 . . ?
C16 C15 H40A 120.1 . . ?
F3 C16 C17 120.8(12) . . ?
F3 C16 C15 118.1(11) . . ?
C17 C16 C15 121.2(12) . . ?
C16 C17 C12 119.5(10) . . ?
C16 C17 C18 125.6(11) . . ?
C12 C17 C18 114.7(10) . . ?
N4 C18 C19 120.8(11) . . ?
N4 C18 C17 112.5(9) . . ?
C19 C18 C17 126.7(11) . . ?
C20 C19 C18 118.8(14) . . ?
C20 C19 H36A 120.6 . . ?
C18 C19 H36A 120.6 . . ?
C21 C20 C19 121.5(13) . . ?
C21 C20 H35A 119.3 . . ?
C19 C20 H35A 119.3 . . ?
C20 C21 C22 117.8(11) . . ?
C20 C21 H34A 121.1 . . ?
C22 C21 H34A 121.1 . . ?
N4 C22 C21 122.4(11) . . ?
N4 C22 H33A 118.8 . . ?
C21 C22 H33A 118.8 . . ?
C24 C23 H1A 109.5 . . ?
C24 C23 H1B 109.5 . . ?
H1A C23 H1B 109.5 . . ?
C24 C23 H1C 109.5 . . ?
H1A C23 H1C 109.5 . . ?
H1B C23 H1C 109.5 . . ?
C25 C24 C23 130.4(11) . . ?
C25 C24 S1 109.7(9) . . ?
C23 C24 S1 119.7(9) . . ?
C24 C25 C26 114.2(11) . . ?
C24 C25 C35 122.5(10) . . ?
C26 C25 C35 123.4(11) . . ?
C27 C26 C25 112.3(13) . . ?
C27 C26 H4A 123.8 . . ?
C25 C26 H4A 123.8 . . ?
C26 C27 C28 126.7(15) . . ?
C26 C27 S1 111.1(11) . . ?
C28 C27 S1 122.1(11) . . ?
C27 C28 H6A 109.5 . . ?
C27 C28 H6B 109.5 . . ?
H6A C28 H6B 109.5 . . ?
C27 C28 H6C 109.5 . . ?
H6A C28 H6C 109.5 . . ?
H6B C28 H6C 109.5 . . ?
C30 C29 H7A 109.5 . . ?
C30 C29 H7B 109.5 . . ?
H7A C29 H7B 109.5 . . ?
C30 C29 H7C 109.5 . . ?
H7A C29 H7C 109.5 . . ?
H7B C29 H7C 109.5 . . ?
C31 C30 C29 129.9(10) . . ?
C31 C30 S2 110.2(8) . . ?
C29 C30 S2 119.9(8) . . ?
C30 C31 C32 111.9(9) . . ?
C30 C31 C36 122.8(9) . . ?
C32 C31 C36 124.9(9) . . ?
C33 C32 C31 116.6(10) . . ?
C33 C32 H10A 121.7 . . ?
C31 C32 H10A 121.7 . . ?
C32 C33 C34 130.9(12) . . ?
C32 C33 S2 108.4(8) . . ?
C34 C33 S2 120.7(10) . . ?
C33 C34 H12A 109.5 . . ?
C33 C34 H12B 109.5 . . ?
H12A C34 H12B 109.5 . . ?
C33 C34 H12C 109.5 . . ?
H12A C34 H12C 109.5 . . ?
H12B C34 H12C 109.5 . . ?
C36 C35 N2 107.7(9) . . ?
C36 C35 C25 130.3(9) . . ?
N2 C35 C25 122.0(9) . . ?
C35 C36 N1 107.3(8) . . ?
C35 C36 C31 128.8(8) . . ?
N1 C36 C31 123.6(8) . . ?
N1 C37 N2 110.7(8) . . ?
N1 C37 C38 127.2(8) . . ?
N2 C37 C38 122.1(8) . . ?
C39 C38 C43 118.4(9) . . ?
C39 C38 C37 121.7(9) . . ?
C43 C38 C37 119.9(9) . . ?
O1 C39 C38 120.5(8) . . ?
O1 C39 C40 120.2(9) . . ?
C38 C39 C40 119.2(9) . . ?
C41 C40 C39 120.4(10) . . ?
C41 C40 H18A 119.8 . . ?
C39 C40 H18A 119.8 . . ?
C40 C41 C42 120.7(11) . . ?
C40 C41 H19A 119.6 . . ?
C42 C41 H19A 119.6 . . ?
C43 C42 C41 119.6(12) . . ?
C43 C42 H20A 120.2 . . ?
C41 C42 H20A 120.2 . . ?
C42 C43 C38 121.3(11) . . ?
C42 C43 H21A 119.3 . . ?
C38 C43 H21A 119.3 . . ?
O2 C44 H44C 107.9 . . ?
O2 C44 H44A 111.8 . . ?
H44C C44 H44A 107.8 . . ?
O2 C44 H44B 111.7 . . ?
H44C C44 H44B 107.8 . . ?
H44A C44 H44B 109.6 . . ?
O3 C45 H45C 103.2 . . ?
O3 C45 H45A 116.0 . . ?
H45C C45 H45A 104.0 . . ?
O3 C45 H45B 115.3 . . ?
H45C C45 H45B 104.0 . . ?
H45A C45 H45B 112.3 . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         2.417
_refine_diff_density_min         -3.240
_refine_diff_density_rms         0.294
####################################################################### 
# 
# 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 1023279'
_audit_update_record             
;
2014-09-07 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C49 H35 F4 Ir N4 O S2'
_chemical_formula_weight         1028.13

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   13.1823(5)
_cell_length_b                   24.5037(10)
_cell_length_c                   14.8078(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.8960(10)
_cell_angle_gamma                90.00
_cell_volume                     4338.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4729
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      21.80

_exptl_crystal_description       blocky
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2040
_exptl_absorpt_coefficient_mu    3.233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_T_max  0.524
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Aepex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29341
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_sigmaI/netI    0.0572
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.70
_diffrn_reflns_theta_max         27.51
_reflns_number_total             9969
_reflns_number_gt                6508
_reflns_threshold_expression     >2sigma(I)

_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  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0830P)²+0.0707P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9969
_refine_ls_number_parameters     550
_refine_ls_number_restraints     101
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1472
_refine_ls_wR_factor_gt          0.1289
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.79327(2) 0.613730(10) 0.727560(19) 0.04899(11) Uani 1 1 d . . .
S1 S 0.43690(19) 0.39633(9) 0.89390(18) 0.0772(6) Uani 1 1 d . . .
S2 S 0.3443(2) 0.61812(12) 0.6534(4) 0.1342(14) Uani 1 1 d DU . .
F1 F 0.4988(4) 0.7600(2) 0.7157(4) 0.0984(16) Uani 1 1 d . . .
F2 F 0.4682(4) 0.7074(2) 0.4034(3) 0.0972(15) Uani 1 1 d . . .
F3 F 1.0726(7) 0.7037(3) 0.6056(6) 0.180(4) Uani 1 1 d . . .
F4 F 1.0167(4) 0.80357(18) 0.8510(4) 0.1001(16) Uani 1 1 d . . .
O1 O 0.9419(3) 0.57467(18) 0.8288(3) 0.0557(11) Uani 1 1 d . . .
N1 N 0.7157(4) 0.5360(2) 0.7363(4) 0.0540(13) Uani 1 1 d . . .
N2 N 0.7211(4) 0.4532(2) 0.7974(4) 0.0496(12) Uani 1 1 d . . .
N3 N 0.7590(4) 0.6433(2) 0.8391(4) 0.0523(13) Uani 1 1 d . . .
N4 N 0.8336(5) 0.5913(2) 0.6142(4) 0.0559(13) Uani 1 1 d . . .
C1 C 0.6607(5) 0.6597(3) 0.6485(5) 0.0527(15) Uani 1 1 d . . .
C2 C 0.6087(6) 0.6667(3) 0.5461(5) 0.0630(18) Uani 1 1 d . . .
H2A H 0.6326 0.6470 0.5051 0.076 Uiso 1 1 calc R . .
C3 C 0.5208(6) 0.7034(3) 0.5053(5) 0.069(2) Uani 1 1 d . . .
C4 C 0.4823(6) 0.7350(4) 0.5599(6) 0.076(2) Uani 1 1 d . . .
H4A H 0.4240 0.7597 0.5307 0.091 Uiso 1 1 calc R . .
C5 C 0.5348(6) 0.7278(3) 0.6597(6) 0.069(2) Uani 1 1 d . . .
C6 C 0.6221(5) 0.6923(3) 0.7069(5) 0.0529(16) Uani 1 1 d . . .
C7 C 0.6790(6) 0.6833(3) 0.8133(5) 0.0589(17) Uani 1 1 d . . .
C8 C 0.6625(7) 0.7101(3) 0.8907(6) 0.078(2) Uani 1 1 d . . .
H8A H 0.6096 0.7378 0.8754 0.094 Uiso 1 1 calc R . .
C9 C 0.7234(8) 0.6958(4) 0.9872(6) 0.094(3) Uani 1 1 d . . .
H9A H 0.7108 0.7136 1.0370 0.113 Uiso 1 1 calc R . .
C10 C 0.8029(8) 0.6557(4) 1.0127(6) 0.084(2) Uani 1 1 d . . .
H10A H 0.8449 0.6462 1.0789 0.100 Uiso 1 1 calc R . .
C11 C 0.8184(6) 0.6298(3) 0.9363(6) 0.0667(19) Uani 1 1 d . . .
H11A H 0.8715 0.6022 0.9521 0.080 Uiso 1 1 calc R . .
C12 C 0.8868(5) 0.6776(3) 0.7280(5) 0.0552(16) Uani 1 1 d . . .
C13 C 0.9145(6) 0.7230(3) 0.7911(5) 0.0614(18) Uani 1 1 d . . .
H13A H 0.8812 0.7276 0.8348 0.074 Uiso 1 1 calc R . .
C14 C 0.9900(7) 0.7605(3) 0.7891(6) 0.073(2) Uani 1 1 d . . .
C15 C 1.0429(9) 0.7555(4) 0.7265(8) 0.109(3) Uani 1 1 d . . .
H15A H 1.0933 0.7817 0.7251 0.131 Uiso 1 1 calc R . .
C16 C 1.0183(9) 0.7104(4) 0.6667(8) 0.097(3) Uani 1 1 d . . .
C17 C 0.9413(7) 0.6709(3) 0.6642(6) 0.070(2) Uani 1 1 d . . .
C18 C 0.9110(6) 0.6228(3) 0.6013(5) 0.0603(18) Uani 1 1 d . . .
C19 C 0.9491(8) 0.6071(4) 0.5301(7) 0.086(3) Uani 1 1 d . . .
H19A H 1.0015 0.6286 0.5199 0.103 Uiso 1 1 calc R . .
C20 C 0.9103(9) 0.5605(4) 0.4752(6) 0.092(3) Uani 1 1 d . . .
H20A H 0.9389 0.5497 0.4303 0.110 Uiso 1 1 calc R . .
C21 C 0.8297(8) 0.5299(4) 0.4864(6) 0.086(2) Uani 1 1 d . . .
H21A H 0.7997 0.4992 0.4474 0.103 Uiso 1 1 calc R . .
C22 C 0.7942(7) 0.5465(3) 0.5582(5) 0.069(2) Uani 1 1 d . . .
H22A H 0.7409 0.5255 0.5679 0.083 Uiso 1 1 calc R . .
C23 C 0.6283(7) 0.4597(4) 0.9892(6) 0.092(3) Uani 1 1 d . . .
H23A H 0.6810 0.4817 0.9764 0.111 Uiso 1 1 calc R . .
H23B H 0.6667 0.4299 1.0321 0.111 Uiso 1 1 calc R . .
H23C H 0.5921 0.4815 1.0208 0.111 Uiso 1 1 calc R . .
C24 C 0.5429(6) 0.4378(3) 0.8935(6) 0.0646(19) Uani 1 1 d . . .
C25 C 0.5338(5) 0.4440(3) 0.7998(5) 0.0563(16) Uani 1 1 d . . .
C26 C 0.4401(6) 0.4157(3) 0.7272(6) 0.0618(18) Uani 1 1 d . . .
H26A H 0.4213 0.4165 0.6592 0.074 Uiso 1 1 calc R . .
C27 C 0.3807(6) 0.3870(3) 0.7696(7) 0.071(2) Uani 1 1 d . . .
C28 C 0.2826(6) 0.3504(4) 0.7202(7) 0.093(3) Uani 1 1 d . . .
H28A H 0.2618 0.3499 0.6498 0.111 Uiso 1 1 calc R . .
H28B H 0.2211 0.3636 0.7326 0.111 Uiso 1 1 calc R . .
H28C H 0.3017 0.3141 0.7464 0.111 Uiso 1 1 calc R . .
C29 C 0.5022(10) 0.5878(5) 0.8552(9) 0.128(4) Uani 1 1 d DU . .
H29A H 0.5719 0.5689 0.8884 0.153 Uiso 1 1 calc R . .
H29B H 0.4460 0.5705 0.8705 0.153 Uiso 1 1 calc R . .
H29C H 0.5108 0.6251 0.8772 0.153 Uiso 1 1 calc R . .
C30 C 0.4700(8) 0.5864(4) 0.7528(8) 0.110(3) Uani 1 1 d DU . .
C31 C 0.5161(6) 0.5622(3) 0.6990(7) 0.080(2) Uani 1 1 d DU . .
C32 C 0.4528(7) 0.5684(4) 0.5869(8) 0.122(3) Uani 1 1 d DU . .
H32A H 0.4744 0.5519 0.5412 0.146 Uiso 1 1 calc R . .
C33 C 0.3625(10) 0.6001(5) 0.5614(9) 0.147(4) Uani 1 1 d DU . .
C34 C 0.2845(11) 0.6172(5) 0.4558(11) 0.173(6) Uani 1 1 d DU . .
H34A H 0.3100 0.6014 0.4096 0.208 Uiso 1 1 calc R . .
H34B H 0.2842 0.6562 0.4506 0.208 Uiso 1 1 calc R . .
H34C H 0.2101 0.6045 0.4406 0.208 Uiso 1 1 calc R . .
C35 C 0.6158(5) 0.4745(3) 0.7762(5) 0.0544(16) Uani 1 1 d . . .
C36 C 0.6136(5) 0.5252(3) 0.7388(5) 0.0558(16) Uani 1 1 d . . .
C37 C 0.7788(5) 0.4914(3) 0.7710(5) 0.0520(15) Uani 1 1 d . . .
C38 C 0.8925(5) 0.4831(3) 0.7783(5) 0.0507(15) Uani 1 1 d . . .
C39 C 0.9680(5) 0.5265(3) 0.8065(5) 0.0509(15) Uani 1 1 d . . .
C40 C 1.0768(6) 0.5172(3) 0.8127(5) 0.0622(18) Uani 1 1 d . . .
H40A H 1.1293 0.5452 0.8328 0.075 Uiso 1 1 calc R . .
C41 C 1.1050(6) 0.4665(3) 0.7889(6) 0.069(2) Uani 1 1 d . . .
H41A H 1.1770 0.4609 0.7940 0.083 Uiso 1 1 calc R . .
C42 C 1.0312(6) 0.4250(3) 0.7585(6) 0.068(2) Uani 1 1 d . . .
H42A H 1.0519 0.3916 0.7416 0.082 Uiso 1 1 calc R . .
C43 C 0.9243(6) 0.4323(3) 0.7525(5) 0.0613(18) Uani 1 1 d . . .
H43A H 0.8733 0.4037 0.7315 0.074 Uiso 1 1 calc R . .
C44 C 0.7620(6) 0.4026(3) 0.8501(5) 0.0542(16) Uani 1 1 d . . .
C45 C 0.8483(6) 0.4030(3) 0.9426(6) 0.0620(18) Uani 1 1 d . . .
H45A H 0.8845 0.4355 0.9703 0.074 Uiso 1 1 calc R . .
C46 C 0.8812(6) 0.3547(3) 0.9948(6) 0.075(2) Uani 1 1 d . . .
H46A H 0.9391 0.3547 1.0584 0.090 Uiso 1 1 calc R . .
C47 C 0.8293(7) 0.3068(3) 0.9535(6) 0.072(2) Uani 1 1 d . . .
H47A H 0.8520 0.2745 0.9893 0.086 Uiso 1 1 calc R . .
C48 C 0.7453(6) 0.3060(3) 0.8610(6) 0.069(2) Uani 1 1 d . . .
H48A H 0.7110 0.2731 0.8334 0.083 Uiso 1 1 calc R . .
C49 C 0.7097(5) 0.3544(3) 0.8067(6) 0.0587(17) Uani 1 1 d . . .
H49A H 0.6522 0.3541 0.7429 0.070 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 C12 1.991(6) . ?
Ir1 C1 1.993(6) . ?
Ir1 N3 2.021(5) . ?
Ir1 N4 2.039(5) . ?
Ir1 O1 2.128(4) . ?
Ir1 N1 2.191(5) . ?
S1 C27 1.685(9) . ?
S1 C24 1.730(7) . ?
S2 C33 1.543(13) . ?
S2 C30 1.862(10) . ?
F1 C5 1.366(9) . ?
F2 C3 1.374(8) . ?
F3 C16 1.379(10) . ?
F4 C14 1.344(9) . ?
O1 C39 1.311(7) . ?
N1 C37 1.338(8) . ?
N1 C36 1.388(8) . ?
N2 C37 1.364(8) . ?
N2 C35 1.389(8) . ?
N2 C44 1.444(8) . ?
N3 C11 1.358(9) . ?
N3 C7 1.371(8) . ?
N4 C22 1.343(9) . ?
N4 C18 1.355(9) . ?
C1 C2 1.386(9) . ?
C1 C6 1.421(9) . ?
C2 C3 1.387(10) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(11) . ?
C4 C5 1.353(10) . ?
C4 H4A 0.9300 . ?
C5 C6 1.375(9) . ?
C6 C7 1.448(9) . ?
C7 C8 1.415(9) . ?
C8 C9 1.357(11) . ?
C8 H8A 0.9300 . ?
C9 C10 1.368(11) . ?
C9 H9A 0.9300 . ?
C10 C11 1.386(10) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 C13 1.398(9) . ?
C12 C17 1.417(9) . ?
C13 C14 1.365(10) . ?
C13 H13A 0.9300 . ?
C14 C15 1.380(11) . ?
C15 C16 1.367(13) . ?
C15 H15A 0.9300 . ?
C16 C17 1.392(10) . ?
C17 C18 1.450(10) . ?
C18 C19 1.400(10) . ?
C19 C20 1.369(12) . ?
C19 H19A 0.9300 . ?
C20 C21 1.366(12) . ?
C20 H20A 0.9300 . ?
C21 C22 1.390(10) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
C23 C24 1.490(10) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.348(9) . ?
C25 C26 1.430(9) . ?
C25 C35 1.473(8) . ?
C26 C27 1.385(10) . ?
C26 H26A 0.9300 . ?
C27 C28 1.487(10) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.392(12) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 C31 1.328(11) . ?
C31 C36 1.477(10) . ?
C31 C32 1.519(11) . ?
C32 C33 1.336(12) . ?
C32 H32A 0.9300 . ?
C33 C34 1.524(13) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.356(9) . ?
C37 C38 1.470(8) . ?
C38 C39 1.396(9) . ?
C38 C43 1.416(9) . ?
C39 C40 1.416(9) . ?
C40 C41 1.386(10) . ?
C40 H40A 0.9300 . ?
C41 C42 1.346(10) . ?
C41 H41A 0.9300 . ?
C42 C43 1.385(9) . ?
C42 H42A 0.9300 . ?
C43 H43A 0.9300 . ?
C44 C45 1.363(10) . ?
C44 C49 1.382(9) . ?
C45 C46 1.379(10) . ?
C45 H45A 0.9300 . ?
C46 C47 1.367(11) . ?
C46 H46A 0.9300 . ?
C47 C48 1.350(10) . ?
C47 H47A 0.9300 . ?
C48 C49 1.399(10) . ?
C48 H48A 0.9300 . ?
C49 H49A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Ir1 C1 86.9(3) . . ?
C12 Ir1 N3 93.8(2) . . ?
C1 Ir1 N3 80.5(2) . . ?
C12 Ir1 N4 80.7(3) . . ?
C1 Ir1 N4 97.8(2) . . ?
N3 Ir1 N4 174.4(2) . . ?
C12 Ir1 O1 88.1(2) . . ?
C1 Ir1 O1 171.0(2) . . ?
N3 Ir1 O1 92.40(19) . . ?
N4 Ir1 O1 88.7(2) . . ?
C12 Ir1 N1 170.8(2) . . ?
C1 Ir1 N1 102.2(2) . . ?
N3 Ir1 N1 89.6(2) . . ?
N4 Ir1 N1 96.0(2) . . ?
O1 Ir1 N1 83.19(18) . . ?
C27 S1 C24 93.5(4) . . ?
C33 S2 C30 99.3(6) . . ?
C39 O1 Ir1 119.3(4) . . ?
C37 N1 C36 106.7(5) . . ?
C37 N1 Ir1 120.2(4) . . ?
C36 N1 Ir1 130.5(4) . . ?
C37 N2 C35 107.6(5) . . ?
C37 N2 C44 128.2(5) . . ?
C35 N2 C44 123.7(5) . . ?
C11 N3 C7 120.2(6) . . ?
C11 N3 Ir1 123.4(5) . . ?
C7 N3 Ir1 116.0(4) . . ?
C22 N4 C18 119.9(6) . . ?
C22 N4 Ir1 124.2(5) . . ?
C18 N4 Ir1 115.8(5) . . ?
C2 C1 C6 117.2(6) . . ?
C2 C1 Ir1 128.4(5) . . ?
C6 C1 Ir1 114.2(4) . . ?
C1 C2 C3 119.7(7) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C4 C3 F2 118.0(7) . . ?
C4 C3 C2 124.1(7) . . ?
F2 C3 C2 118.0(8) . . ?
C5 C4 C3 115.3(7) . . ?
C5 C4 H4A 122.4 . . ?
C3 C4 H4A 122.4 . . ?
C4 C5 F1 116.1(7) . . ?
C4 C5 C6 124.9(8) . . ?
F1 C5 C6 119.0(7) . . ?
C5 C6 C1 118.9(6) . . ?
C5 C6 C7 126.1(7) . . ?
C1 C6 C7 115.0(6) . . ?
N3 C7 C8 117.9(6) . . ?
N3 C7 C6 113.4(6) . . ?
C8 C7 C6 128.6(6) . . ?
C9 C8 C7 120.5(7) . . ?
C9 C8 H8A 119.7 . . ?
C7 C8 H8A 119.7 . . ?
C8 C9 C10 121.4(7) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C9 C10 C11 117.6(8) . . ?
C9 C10 H10A 121.2 . . ?
C11 C10 H10A 121.2 . . ?
N3 C11 C10 122.4(7) . . ?
N3 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
C13 C12 C17 118.4(6) . . ?
C13 C12 Ir1 127.9(5) . . ?
C17 C12 Ir1 113.2(5) . . ?
C14 C13 C12 120.6(7) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
F4 C14 C13 119.9(8) . . ?
F4 C14 C15 117.8(7) . . ?
C13 C14 C15 122.3(8) . . ?
C16 C15 C14 117.2(8) . . ?
C16 C15 H15A 121.4 . . ?
C14 C15 H15A 121.4 . . ?
C15 C16 F3 118.3(8) . . ?
C15 C16 C17 123.5(8) . . ?
F3 C16 C17 118.3(8) . . ?
C16 C17 C12 118.0(8) . . ?
C16 C17 C18 125.7(7) . . ?
C12 C17 C18 116.3(6) . . ?
N4 C18 C19 118.7(7) . . ?
N4 C18 C17 113.1(6) . . ?
C19 C18 C17 128.2(7) . . ?
C20 C19 C18 120.9(8) . . ?
C20 C19 H19A 119.5 . . ?
C18 C19 H19A 119.5 . . ?
C21 C20 C19 120.1(8) . . ?
C21 C20 H20A 120.0 . . ?
C19 C20 H20A 120.0 . . ?
C20 C21 C22 117.5(8) . . ?
C20 C21 H21A 121.2 . . ?
C22 C21 H21A 121.2 . . ?
N4 C22 C21 122.9(7) . . ?
N4 C22 H22A 118.6 . . ?
C21 C22 H22A 118.6 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C23 130.0(7) . . ?
C25 C24 S1 110.3(5) . . ?
C23 C24 S1 119.7(6) . . ?
C24 C25 C26 113.3(6) . . ?
C24 C25 C35 123.0(6) . . ?
C26 C25 C35 123.7(6) . . ?
C27 C26 C25 112.2(7) . . ?
C27 C26 H26A 123.9 . . ?
C25 C26 H26A 123.9 . . ?
C26 C27 C28 128.5(8) . . ?
C26 C27 S1 110.7(6) . . ?
C28 C27 S1 120.7(6) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C29 131.2(9) . . ?
C31 C30 S2 101.0(7) . . ?
C29 C30 S2 127.8(8) . . ?
C30 C31 C36 125.1(8) . . ?
C30 C31 C32 115.6(8) . . ?
C36 C31 C32 118.8(8) . . ?
C33 C32 C31 112.4(11) . . ?
C33 C32 H32A 123.8 . . ?
C31 C32 H32A 123.8 . . ?
C32 C33 C34 125.9(13) . . ?
C32 C33 S2 111.6(10) . . ?
C34 C33 S2 122.6(11) . . ?
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 . . ?
C36 C35 N2 106.5(5) . . ?
C36 C35 C25 132.1(6) . . ?
N2 C35 C25 121.3(6) . . ?
C35 C36 N1 109.4(6) . . ?
C35 C36 C31 126.2(6) . . ?
N1 C36 C31 124.3(6) . . ?
N1 C37 N2 109.8(5) . . ?
N1 C37 C38 126.3(6) . . ?
N2 C37 C38 123.9(6) . . ?
C39 C38 C43 119.7(6) . . ?
C39 C38 C37 119.5(6) . . ?
C43 C38 C37 120.8(6) . . ?
O1 C39 C38 122.2(6) . . ?
O1 C39 C40 119.6(6) . . ?
C38 C39 C40 118.2(6) . . ?
C41 C40 C39 120.0(7) . . ?
C41 C40 H40A 120.0 . . ?
C39 C40 H40A 120.0 . . ?
C42 C41 C40 121.9(7) . . ?
C42 C41 H41A 119.0 . . ?
C40 C41 H41A 119.0 . . ?
C41 C42 C43 119.8(6) . . ?
C41 C42 H42A 120.1 . . ?
C43 C42 H42A 120.1 . . ?
C42 C43 C38 120.3(6) . . ?
C42 C43 H43A 119.9 . . ?
C38 C43 H43A 119.9 . . ?
C45 C44 C49 121.0(7) . . ?
C45 C44 N2 120.1(6) . . ?
C49 C44 N2 118.9(6) . . ?
C44 C45 C46 119.3(7) . . ?
C44 C45 H45A 120.4 . . ?
C46 C45 H45A 120.4 . . ?
C47 C46 C45 120.4(8) . . ?
C47 C46 H46A 119.8 . . ?
C45 C46 H46A 119.8 . . ?
C48 C47 C46 120.6(7) . . ?
C48 C47 H47A 119.7 . . ?
C46 C47 H47A 119.7 . . ?
C47 C48 C49 120.2(7) . . ?
C47 C48 H48A 119.9 . . ?
C49 C48 H48A 119.9 . . ?
C44 C49 C48 118.5(7) . . ?
C44 C49 H49A 120.8 . . ?
C48 C49 H49A 120.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.877
_refine_diff_density_min         -1.156
_refine_diff_density_rms         0.112
