# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'Dalton Trans.'
_journal_coden_cambridge         0222
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Renjie Wang'
_publ_contact_author_name        'Renjie Wang'
_publ_contact_author_email       wangchu809@yahoo.com.cn

data_1
_database_code_depnum_ccdc_archive 'CCDC 790656'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C33 H25 F6 Ir N2 O4 S2'
_chemical_formula_weight         883.87

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'
Ir Ir -1.4442 7.9887 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Iba2

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

_cell_length_a                   11.985(6)
_cell_length_b                   16.493(8)
_cell_length_c                   17.398(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3439(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3080
_cell_measurement_theta_min      3.156
_cell_measurement_theta_max      22.985

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1728
_exptl_absorpt_coefficient_mu    4.075
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  '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            7779
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_sigmaI/netI    0.0479
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2940
_reflns_number_gt                2278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0514P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.00268(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.015(19)
_refine_ls_number_reflns         2940
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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 1.5000 0.5000 0.97913(11) 0.04493(17) Uani 1 2 d S . .
S1 S 1.3284(2) 0.26520(12) 0.92665(13) 0.0659(6) Uani 1 1 d . . .
C4 C 1.5726(8) 0.4303(6) 0.8989(4) 0.054(2) Uani 1 1 d . . .
N1 N 1.3874(5) 0.4072(3) 0.9733(4) 0.0458(13) Uani 1 1 d . . .
C17 C 1.2435(7) 0.3152(4) 0.9933(4) 0.0533(19) Uani 1 1 d . . .
C10 C 1.4182(7) 0.3468(5) 0.9273(5) 0.0522(18) Uani 1 1 d . . .
C16 C 1.1436(8) 0.2885(5) 1.0254(5) 0.063(2) Uani 1 1 d . . .
H16A H 1.1154 0.2374 1.0140 0.076 Uiso 1 1 calc R . .
C11 C 1.2849(7) 0.3924(5) 1.0088(4) 0.0475(18) Uani 1 1 d . . .
F3 F 0.9540(5) 0.2388(4) 1.1010(4) 0.0863(16) Uani 1 1 d . . .
C12 C 1.2291(6) 0.4434(5) 1.0568(4) 0.0542(19) Uani 1 1 d . . .
H12A H 1.2569 0.4950 1.0665 0.065 Uiso 1 1 calc R . .
O1 O 1.4205(4) 0.5691(3) 1.0672(3) 0.0469(13) Uani 1 1 d . . .
C2 C 1.5000 0.5000 1.1731(8) 0.069(4) Uani 1 2 d S . .
H2A H 1.5000 0.5000 1.2265 0.083 Uiso 1 2 calc SR . .
C6 C 1.7086(8) 0.3917(7) 0.8023(5) 0.075(3) Uani 1 1 d . . .
H6A H 1.7724 0.4040 0.7743 0.089 Uiso 1 1 calc R . .
C9 C 1.5209(7) 0.3573(6) 0.8841(5) 0.056(2) Uani 1 1 d . . .
C5 C 1.6697(8) 0.4472(6) 0.8572(4) 0.061(2) Uani 1 1 d . . .
H5A H 1.7084 0.4953 0.8658 0.073 Uiso 1 1 calc R . .
C8 C 1.5612(10) 0.3014(6) 0.8292(6) 0.073(3) Uani 1 1 d . . .
H8A H 1.5237 0.2529 0.8209 0.087 Uiso 1 1 calc R . .
C7 C 1.6540(8) 0.3187(7) 0.7888(5) 0.074(3) Uani 1 1 d . . .
H7A H 1.6812 0.2824 0.7525 0.089 Uiso 1 1 calc R . .
C14 C 1.0880(8) 0.3396(6) 1.0742(5) 0.065(2) Uani 1 1 d . . .
C1 C 1.4327(7) 0.5585(5) 1.1393(4) 0.053(2) Uani 1 1 d . . .
C13 C 1.1308(7) 0.4182(5) 1.0914(5) 0.062(2) Uani 1 1 d . . .
H13A H 1.0933 0.4522 1.1254 0.074 Uiso 1 1 calc R . .
C3 C 1.3602(9) 0.6119(6) 1.1886(5) 0.072(3) Uani 1 1 d . . .
H3A H 1.3639 0.6667 1.1702 0.108 Uiso 1 1 calc R . .
H3B H 1.3859 0.6099 1.2408 0.108 Uiso 1 1 calc R . .
H3C H 1.2844 0.5931 1.1862 0.108 Uiso 1 1 calc R . .
F2 F 0.9809(7) 0.3293(8) 1.1865(5) 0.155(5) Uani 1 1 d . . .
O1W O 0.9428(6) 0.4243(3) 1.3547(4) 0.072(2) Uani 1 1 d . . .
F1 F 0.8967(6) 0.3626(5) 1.0843(6) 0.127(3) Uani 1 1 d . . .
C15 C 0.9796(10) 0.3186(9) 1.1120(8) 0.090(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.0553(2) 0.0456(2) 0.0339(2) 0.000 0.000 -0.00479(18)
S1 0.0744(13) 0.0545(12) 0.0688(12) -0.0175(12) -0.0081(12) -0.0066(11)
C4 0.077(7) 0.062(6) 0.024(4) 0.000(3) -0.010(4) 0.011(5)
N1 0.057(3) 0.040(3) 0.040(3) -0.005(3) -0.007(4) -0.010(2)
C17 0.058(4) 0.059(5) 0.043(5) 0.004(3) -0.008(4) -0.005(4)
C10 0.064(5) 0.043(4) 0.050(4) 0.000(4) -0.014(4) 0.001(4)
C16 0.069(6) 0.055(6) 0.064(5) -0.002(4) -0.027(5) -0.021(4)
C11 0.054(5) 0.048(4) 0.041(4) 0.001(3) -0.006(3) -0.002(3)
F3 0.070(3) 0.068(4) 0.121(5) 0.003(3) 0.000(4) -0.022(3)
C12 0.055(5) 0.044(4) 0.063(5) -0.005(4) -0.009(4) -0.011(4)
O1 0.048(3) 0.046(3) 0.047(3) -0.003(2) 0.007(3) -0.013(2)
C2 0.068(8) 0.106(13) 0.034(6) 0.000 0.000 -0.035(8)
C6 0.067(6) 0.111(9) 0.046(5) -0.012(5) -0.002(4) 0.021(6)
C9 0.073(6) 0.059(6) 0.037(4) -0.005(4) -0.012(4) 0.008(4)
C5 0.054(5) 0.076(6) 0.052(5) 0.004(4) -0.003(4) 0.006(5)
C8 0.081(7) 0.060(6) 0.076(6) -0.011(5) -0.022(6) 0.019(5)
C7 0.070(6) 0.096(8) 0.056(5) -0.020(5) 0.010(5) 0.023(6)
C14 0.066(5) 0.080(6) 0.049(5) 0.010(5) -0.005(4) -0.020(5)
C1 0.049(5) 0.075(6) 0.035(4) -0.008(4) 0.002(4) -0.026(4)
C13 0.068(5) 0.052(5) 0.066(5) -0.015(4) 0.002(5) -0.012(4)
C3 0.079(6) 0.087(7) 0.050(5) -0.015(5) -0.001(5) -0.012(6)
F2 0.172(8) 0.214(12) 0.080(5) -0.039(6) 0.050(5) -0.112(8)
O1W 0.060(4) 0.030(3) 0.127(6) -0.036(3) 0.022(4) -0.014(3)
F1 0.076(4) 0.105(6) 0.201(8) 0.041(6) 0.044(5) 0.021(4)
C15 0.087(8) 0.099(10) 0.085(9) 0.021(7) -0.005(6) -0.048(7)

_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 C4 2.007(9) . ?
Ir1 C4 2.007(9) 2_865 ?
Ir1 N1 2.043(5) . ?
Ir1 N1 2.043(5) 2_865 ?
Ir1 O1 2.134(6) 2_865 ?
Ir1 O1 2.134(6) . ?
S1 C10 1.723(8) . ?
S1 C17 1.748(8) . ?
C4 C9 1.379(13) . ?
C4 C5 1.400(12) . ?
N1 C10 1.331(9) . ?
N1 C11 1.396(10) . ?
C17 C16 1.393(12) . ?
C17 C11 1.394(9) . ?
C10 C9 1.453(12) . ?
C16 C14 1.369(14) . ?
C11 C12 1.360(11) . ?
F3 C15 1.365(16) . ?
C12 C13 1.386(11) . ?
O1 C1 1.275(9) . ?
C2 C1 1.388(10) 2_865 ?
C2 C1 1.388(10) . ?
C6 C7 1.389(14) . ?
C6 C5 1.402(12) . ?
C9 C8 1.412(13) . ?
C8 C7 1.346(15) . ?
C14 C13 1.427(13) . ?
C14 C15 1.496(15) . ?
C1 C3 1.505(12) . ?
F2 C15 1.308(16) . ?
F1 C15 1.321(15) . ?

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
C4 Ir1 C4 91.8(5) . 2_865 ?
C4 Ir1 N1 79.8(3) . . ?
C4 Ir1 N1 96.2(3) 2_865 . ?
C4 Ir1 N1 96.2(3) . 2_865 ?
C4 Ir1 N1 79.8(3) 2_865 2_865 ?
N1 Ir1 N1 174.3(4) . 2_865 ?
C4 Ir1 O1 90.0(2) . 2_865 ?
C4 Ir1 O1 177.3(4) 2_865 2_865 ?
N1 Ir1 O1 86.0(2) . 2_865 ?
N1 Ir1 O1 98.1(2) 2_865 2_865 ?
C4 Ir1 O1 177.3(4) . . ?
C4 Ir1 O1 90.0(2) 2_865 . ?
N1 Ir1 O1 98.1(2) . . ?
N1 Ir1 O1 86.0(2) 2_865 . ?
O1 Ir1 O1 88.2(3) 2_865 . ?
C10 S1 C17 89.5(4) . . ?
C9 C4 C5 116.8(8) . . ?
C9 C4 Ir1 115.8(7) . . ?
C5 C4 Ir1 127.4(7) . . ?
C10 N1 C11 112.3(6) . . ?
C10 N1 Ir1 114.1(5) . . ?
C11 N1 Ir1 133.6(5) . . ?
C16 C17 C11 121.1(7) . . ?
C16 C17 S1 128.2(6) . . ?
C11 C17 S1 110.6(6) . . ?
N1 C10 C9 117.2(7) . . ?
N1 C10 S1 114.6(6) . . ?
C9 C10 S1 128.2(6) . . ?
C14 C16 C17 118.3(8) . . ?
C12 C11 C17 120.6(7) . . ?
C12 C11 N1 126.6(7) . . ?
C17 C11 N1 112.8(6) . . ?
C11 C12 C13 119.9(7) . . ?
C1 O1 Ir1 125.6(6) . . ?
C1 C2 C1 129.9(12) 2_865 . ?
C7 C6 C5 121.7(9) . . ?
C4 C9 C8 122.8(9) . . ?
C4 C9 C10 112.9(8) . . ?
C8 C9 C10 124.2(9) . . ?
C4 C5 C6 119.9(10) . . ?
C7 C8 C9 119.8(10) . . ?
C8 C7 C6 119.0(8) . . ?
C16 C14 C13 120.9(8) . . ?
C16 C14 C15 123.6(10) . . ?
C13 C14 C15 115.5(10) . . ?
O1 C1 C2 125.3(9) . . ?
O1 C1 C3 114.5(8) . . ?
C2 C1 C3 120.1(8) . . ?
C12 C13 C14 119.2(8) . . ?
F2 C15 F1 107.2(15) . . ?
F2 C15 F3 105.8(11) . . ?
F1 C15 F3 108.0(9) . . ?
F2 C15 C14 113.2(10) . . ?
F1 C15 C14 111.4(10) . . ?
F3 C15 C14 110.9(12) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.223
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.119