# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_r141009e1-sr
_audit_block_doi                 10.5517/cc14282k
_database_code_depnum_ccdc_archive 'CCDC 1044857'
_audit_update_record             
;
2015-01-22 deposited with the CCDC.
2015-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H34 Cl2 Ir N P2'
_chemical_formula_weight         829.70

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Ibam

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

_cell_length_a                   30.868(6)
_cell_length_b                   17.517(4)
_cell_length_c                   24.155(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     13061(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12015
_cell_measurement_theta_min      1.9503
_cell_measurement_theta_max      27.8744

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    0.844
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3280
_exptl_absorpt_coefficient_mu    2.190
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_T_max  0.7208
_exptl_absorpt_process_details   Crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            79545
_diffrn_reflns_av_R_equivalents  0.0814
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.89
_reflns_number_total             7979
_reflns_number_gt                6086
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       Crystalclear
_computing_cell_refinement       Crystalclear
_computing_data_reduction        Crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.1085P)²+18.1662P] 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     SHELXL
_refine_ls_extinction_coef       0.00033(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7979
_refine_ls_number_parameters     208
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0719
_refine_ls_wR_factor_ref         0.2174
_refine_ls_wR_factor_gt          0.2005
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.002
_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 0.755116(13) 0.256809(19) 0.5000 0.05504(19) Uani 1 2 d SD . .
H1 H 0.7035(4) 0.250(5) 0.5000 0.083 Uiso 1 2 d SD . .
P1 P 0.75248(6) 0.25319(9) 0.59590(9) 0.0559(4) Uani 1 1 d . . .
Cl1 Cl 0.75047(9) 0.12054(14) 0.5000 0.0758(8) Uani 1 2 d S . .
Cl2 Cl 0.83808(9) 0.27424(13) 0.5000 0.0710(6) Uani 1 2 d S . .
N1 N 0.7559(2) 0.3775(4) 0.5000 0.0501(17) Uani 1 2 d S . .
H1A H 0.7844 0.3912 0.5000 0.060 Uiso 1 2 calc SR . .
C1 C 0.7804(2) 0.1734(3) 0.6318(3) 0.0614(16) Uani 1 1 d . . .
C2 C 0.8160(3) 0.1404(4) 0.6071(3) 0.096(3) Uani 1 1 d . . .
H2 H 0.8256 0.1568 0.5726 0.115 Uiso 1 1 calc R . .
C3 C 0.8374(4) 0.0818(5) 0.6350(4) 0.137(5) Uani 1 1 d . . .
H3 H 0.8628 0.0619 0.6201 0.165 Uiso 1 1 calc R . .
C4 C 0.8222(4) 0.0534(5) 0.6827(4) 0.106(3) Uani 1 1 d . . .
H4 H 0.8354 0.0112 0.6989 0.127 Uiso 1 1 calc R . .
C5 C 0.7865(3) 0.0875(5) 0.7081(3) 0.093(3) Uani 1 1 d . . .
H5 H 0.7765 0.0697 0.7421 0.112 Uiso 1 1 calc R . .
C6 C 0.7666(3) 0.1472(4) 0.6823(3) 0.077(2) Uani 1 1 d . . .
H6 H 0.7431 0.1706 0.6994 0.092 Uiso 1 1 calc R . .
C7 C 0.6999(3) 0.2493(4) 0.6258(3) 0.0697(18) Uani 1 1 d . . .
C8 C 0.6865(3) 0.2968(5) 0.6704(3) 0.097(3) Uani 1 1 d . . .
H8 H 0.7035 0.3375 0.6821 0.116 Uiso 1 1 calc R . .
C9 C 0.6456(4) 0.2797(8) 0.6968(5) 0.140(4) Uani 1 1 d . . .
H9 H 0.6369 0.3068 0.7279 0.168 Uiso 1 1 calc R . .
C10 C 0.6195(4) 0.2231(8) 0.6757(5) 0.134(4) Uani 1 1 d . . .
H10 H 0.5925 0.2146 0.6917 0.161 Uiso 1 1 calc R . .
C11 C 0.6312(3) 0.1821(7) 0.6348(5) 0.125(4) Uani 1 1 d . . .
H11 H 0.6129 0.1440 0.6219 0.150 Uiso 1 1 calc R . .
C12 C 0.6724(3) 0.1936(5) 0.6083(4) 0.109(3) Uani 1 1 d . . .
H12 H 0.6803 0.1627 0.5787 0.131 Uiso 1 1 calc R . .
C13 C 0.7752(3) 0.3390(3) 0.6253(2) 0.0614(16) Uani 1 1 d . . .
C14 C 0.8039(3) 0.3377(4) 0.6705(3) 0.081(2) Uani 1 1 d . . .
H14 H 0.8121 0.2913 0.6860 0.098 Uiso 1 1 calc R . .
C15 C 0.8201(3) 0.4055(5) 0.6918(3) 0.089(2) Uani 1 1 d . . .
H15 H 0.8386 0.4048 0.7223 0.107 Uiso 1 1 calc R . .
C16 C 0.8088(3) 0.4731(5) 0.6680(3) 0.093(3) Uani 1 1 d . . .
H16 H 0.8192 0.5186 0.6828 0.111 Uiso 1 1 calc R . .
C17 C 0.7824(3) 0.4746(4) 0.6227(3) 0.086(3) Uani 1 1 d . . .
H17 H 0.7758 0.5214 0.6065 0.103 Uiso 1 1 calc R . .
C18 C 0.7651(2) 0.4091(4) 0.6000(2) 0.0636(17) Uani 1 1 d . . .
C19 C 0.7365(2) 0.4137(4) 0.5505(2) 0.0654(18) Uani 1 1 d . . .
H19A H 0.7304 0.4669 0.5427 0.078 Uiso 1 1 calc R . .
H19B H 0.7092 0.3887 0.5588 0.078 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 N1 2.115(7) . ?
Ir1 P1 2.319(2) 10_556 ?
Ir1 P1 2.319(2) . ?
Ir1 Cl1 2.391(3) . ?
Ir1 Cl2 2.579(3) . ?
Ir1 H1 1.597(10) . ?
P1 C7 1.778(8) . ?
P1 C13 1.805(6) . ?
P1 C1 1.856(6) . ?
N1 C19 1.501(7) 10_556 ?
N1 C19 1.501(7) . ?
N1 H1A 0.9100 . ?
C1 C6 1.372(9) . ?
C1 C2 1.378(10) . ?
C2 C3 1.394(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.340(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(10) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C12 1.361(11) . ?
C7 C8 1.421(10) . ?
C8 C9 1.447(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.374(16) . ?
C9 H9 0.9300 . ?
C10 C11 1.276(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.437(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.406(10) . ?
C13 C18 1.406(9) . ?
C14 C15 1.389(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(11) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(11) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.488(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 P1 91.59(4) . 10_556 ?
N1 Ir1 P1 91.59(4) . . ?
P1 Ir1 P1 174.90(9) 10_556 . ?
N1 Ir1 Cl1 177.3(2) . . ?
P1 Ir1 Cl1 88.32(4) 10_556 . ?
P1 Ir1 Cl1 88.32(4) . . ?
N1 Ir1 Cl2 82.5(2) . . ?
P1 Ir1 Cl2 92.18(5) 10_556 . ?
P1 Ir1 Cl2 92.18(5) . . ?
Cl1 Ir1 Cl2 100.24(8) . . ?
N1 Ir1 H1 95(3) . . ?
P1 Ir1 H1 87.88(9) 10_556 . ?
P1 Ir1 H1 87.88(9) . . ?
Cl1 Ir1 H1 82(3) . . ?
Cl2 Ir1 H1 177(3) . . ?
C7 P1 C13 103.1(3) . . ?
C7 P1 C1 101.8(3) . . ?
C13 P1 C1 105.3(3) . . ?
C7 P1 Ir1 116.1(3) . . ?
C13 P1 Ir1 110.9(2) . . ?
C1 P1 Ir1 118.1(2) . . ?
C19 N1 C19 108.8(7) 10_556 . ?
C19 N1 Ir1 114.7(4) 10_556 . ?
C19 N1 Ir1 114.7(4) . . ?
C19 N1 H1A 106.0 10_556 . ?
C19 N1 H1A 106.0 . . ?
Ir1 N1 H1A 106.0 . . ?
C6 C1 C2 119.4(7) . . ?
C6 C1 P1 121.6(6) . . ?
C2 C1 P1 119.0(5) . . ?
C1 C2 C3 118.7(8) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.5(10) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 119.7(8) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 118.9(8) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.6(8) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C12 C7 C8 118.3(8) . . ?
C12 C7 P1 118.1(7) . . ?
C8 C7 P1 123.4(6) . . ?
C7 C8 C9 117.8(9) . . ?
C7 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C10 C9 C8 119.9(10) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 121.7(11) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C10 C11 C12 121.2(10) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C7 C12 C11 120.9(9) . . ?
C7 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C18 119.5(6) . . ?
C14 C13 P1 122.5(5) . . ?
C18 C13 P1 118.0(5) . . ?
C15 C14 C13 120.1(7) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 119.6(8) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.6(7) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C16 C17 C18 122.2(7) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C17 C18 C13 117.9(7) . . ?
C17 C18 C19 120.2(6) . . ?
C13 C18 C19 121.9(6) . . ?
C18 C19 N1 113.1(6) . . ?
C18 C19 H19A 109.0 . . ?
N1 C19 H19A 109.0 . . ?
C18 C19 H19B 109.0 . . ?
N1 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Ir1 P1 C7 92.4(3) . . . . ?
P1 Ir1 P1 C7 -36.1(10) 10_556 . . . ?
Cl1 Ir1 P1 C7 -84.9(2) . . . . ?
Cl2 Ir1 P1 C7 174.9(2) . . . . ?
N1 Ir1 P1 C13 -24.8(3) . . . . ?
P1 Ir1 P1 C13 -153.3(9) 10_556 . . . ?
Cl1 Ir1 P1 C13 157.9(3) . . . . ?
Cl2 Ir1 P1 C13 57.7(3) . . . . ?
N1 Ir1 P1 C1 -146.4(3) . . . . ?
P1 Ir1 P1 C1 85.1(10) 10_556 . . . ?
Cl1 Ir1 P1 C1 36.4(3) . . . . ?
Cl2 Ir1 P1 C1 -63.8(3) . . . . ?
P1 Ir1 N1 C19 24.5(5) 10_556 . . 10_556 ?
P1 Ir1 N1 C19 -151.5(5) . . . 10_556 ?
Cl1 Ir1 N1 C19 -63.5(5) . . . 10_556 ?
Cl2 Ir1 N1 C19 116.5(5) . . . 10_556 ?
P1 Ir1 N1 C19 151.5(5) 10_556 . . . ?
P1 Ir1 N1 C19 -24.5(5) . . . . ?
Cl1 Ir1 N1 C19 63.5(5) . . . . ?
Cl2 Ir1 N1 C19 -116.5(5) . . . . ?
C7 P1 C1 C6 -23.5(7) . . . . ?
C13 P1 C1 C6 83.8(7) . . . . ?
Ir1 P1 C1 C6 -151.8(5) . . . . ?
C7 P1 C1 C2 157.1(7) . . . . ?
C13 P1 C1 C2 -95.6(7) . . . . ?
Ir1 P1 C1 C2 28.8(7) . . . . ?
C6 C1 C2 C3 -1.0(13) . . . . ?
P1 C1 C2 C3 178.4(8) . . . . ?
C1 C2 C3 C4 5.1(17) . . . . ?
C2 C3 C4 C5 -6.0(17) . . . . ?
C3 C4 C5 C6 2.9(15) . . . . ?
C4 C5 C6 C1 1.1(13) . . . . ?
C2 C1 C6 C5 -2.0(12) . . . . ?
P1 C1 C6 C5 178.6(6) . . . . ?
C13 P1 C7 C12 174.5(7) . . . . ?
C1 P1 C7 C12 -76.5(7) . . . . ?
Ir1 P1 C7 C12 53.0(7) . . . . ?
C13 P1 C7 C8 -11.2(7) . . . . ?
C1 P1 C7 C8 97.7(7) . . . . ?
Ir1 P1 C7 C8 -132.7(6) . . . . ?
C12 C7 C8 C9 4.1(14) . . . . ?
P1 C7 C8 C9 -170.2(8) . . . . ?
C7 C8 C9 C10 -5.3(19) . . . . ?
C8 C9 C10 C11 4(2) . . . . ?
C9 C10 C11 C12 -1(2) . . . . ?
C8 C7 C12 C11 -1.3(14) . . . . ?
P1 C7 C12 C11 173.3(8) . . . . ?
C10 C11 C12 C7 -0.5(18) . . . . ?
C7 P1 C13 C14 99.7(7) . . . . ?
C1 P1 C13 C14 -6.7(7) . . . . ?
Ir1 P1 C13 C14 -135.4(6) . . . . ?
C7 P1 C13 C18 -83.5(6) . . . . ?
C1 P1 C13 C18 170.2(5) . . . . ?
Ir1 P1 C13 C18 41.4(6) . . . . ?
C18 C13 C14 C15 3.9(11) . . . . ?
P1 C13 C14 C15 -179.3(6) . . . . ?
C13 C14 C15 C16 -1.6(13) . . . . ?
C14 C15 C16 C17 -1.2(14) . . . . ?
C15 C16 C17 C18 1.8(14) . . . . ?
C16 C17 C18 C13 0.6(12) . . . . ?
C16 C17 C18 C19 -180.0(8) . . . . ?
C14 C13 C18 C17 -3.3(11) . . . . ?
P1 C13 C18 C17 179.7(6) . . . . ?
C14 C13 C18 C19 177.2(7) . . . . ?
P1 C13 C18 C19 0.3(9) . . . . ?
C17 C18 C19 N1 114.0(8) . . . . ?
C13 C18 C19 N1 -66.6(9) . . . . ?
C19 N1 C19 C18 -154.7(4) 10_556 . . . ?
Ir1 N1 C19 C18 75.4(7) . . . . ?

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.019 -0.007 3635 862 ' '
2 0.500 -0.031 0.020 3635 862 ' '
_platon_squeeze_details          
; 
;

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.89
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.484
_refine_diff_density_min         -1.703
_refine_diff_density_rms         0.125
