# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_import01
_database_code_depnum_ccdc_archive 'CCDC 1574554'
_audit_update_record             
;
2017-09-14 deposited with the CCDC.
2017-11-20 downloaded from the CCDC.
;

_audit_creation_date             2016-07-26T11:04:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C44 H66 Ir2 N2 O4 P4 '
_chemical_formula_sum            'C44 H66 Ir2 N2 O4 P4 '
_chemical_formula_weight         1195.31
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
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                   14.6367(7)
_cell_length_b                   11.0939(6)
_cell_length_c                   14.9574(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.785(2)
_cell_angle_gamma                90
_cell_volume                     2423.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9611
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      32.58
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1180
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    5.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min  0.8974
_exptl_absorpt_correction_T_max  0.9751

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       ω-φ
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_number            71770
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             4435
_reflns_number_gt                4176
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0416P)²+6.8344P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4435
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_ref         0.0856
_refine_ls_wR_factor_gt          0.0734
_refine_ls_goodness_of_fit_ref   1.293
_refine_ls_restrained_S_all      1.293
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.299
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.246

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
C1 C 0.8637(3) 1.2394(5) 0.9144(3) 0.0301(11) Uani 1 1 d . . .
C2 C 0.8358(5) 1.3642(5) 0.9123(4) 0.0520(17) Uani 1 1 d . . .
H2A H 0.7975 1.3803 0.9624 0.078 Uiso 1 1 calc R . .
H2B H 0.8008 1.3812 0.8556 0.078 Uiso 1 1 calc R . .
H2C H 0.8902 1.416 0.9177 0.078 Uiso 1 1 calc R . .
C3 C 0.9557(5) 0.9634(5) 0.7118(4) 0.0422(14) Uani 1 1 d . . .
C4 C 0.9127(6) 1.0889(8) 0.7039(5) 0.068(2) Uani 1 1 d . . .
H4A H 0.9303 1.1356 0.7579 0.102 Uiso 1 1 calc R . .
H4B H 0.8459 1.0814 0.6973 0.102 Uiso 1 1 calc R . .
H4C H 0.9344 1.1301 0.6513 0.102 Uiso 1 1 calc R . .
C5 C 0.9343(5) 0.8931(8) 0.6237(4) 0.0593(19) Uani 1 1 d . . .
H5A H 0.9563 0.939 0.5734 0.089 Uiso 1 1 calc R . .
H5B H 0.8681 0.881 0.6143 0.089 Uiso 1 1 calc R . .
H5C H 0.9651 0.8146 0.6274 0.089 Uiso 1 1 calc R . .
C6 C 1.0585(4) 0.9742(5) 0.7280(4) 0.0408(14) Uani 1 1 d . . .
H6A H 1.0837 1.0153 0.677 0.061 Uiso 1 1 calc R . .
H6B H 1.0855 0.8936 0.7346 0.061 Uiso 1 1 calc R . .
H6C H 1.073 1.0208 0.7828 0.061 Uiso 1 1 calc R . .
C7 C 0.9525(4) 0.7304(5) 0.7980(3) 0.0348(12) Uani 1 1 d . . .
C8 C 1.0377(4) 0.7034(5) 0.8410(4) 0.0368(12) Uani 1 1 d . . .
H8 H 1.0696 0.7629 0.8764 0.044 Uiso 1 1 calc R . .
C9 C 1.0758(5) 0.5892(6) 0.8319(5) 0.0554(18) Uani 1 1 d . . .
H9 H 1.1332 0.571 0.8624 0.067 Uiso 1 1 calc R . .
C10 C 1.0314(6) 0.5023(7) 0.7793(5) 0.067(2) Uani 1 1 d . . .
H10 H 1.0595 0.4262 0.7711 0.08 Uiso 1 1 calc R . .
C11 C 0.9466(6) 0.5263(6) 0.7389(5) 0.059(2) Uani 1 1 d . . .
H11 H 0.9142 0.4653 0.7055 0.071 Uiso 1 1 calc R . .
C12 C 0.9078(5) 0.6404(6) 0.7468(4) 0.0479(15) Uani 1 1 d . . .
H12 H 0.8499 0.657 0.7168 0.058 Uiso 1 1 calc R . .
C14 C 0.7213(4) 1.0284(4) 1.0306(4) 0.0278(11) Uani 1 1 d . . .
C15 C 0.6304(4) 1.0550(5) 1.0059(4) 0.0390(13) Uani 1 1 d . . .
H15 H 0.5984 1.0101 0.9597 0.047 Uiso 1 1 calc R . .
C16 C 0.5862(4) 1.1478(7) 1.0491(4) 0.0496(16) Uani 1 1 d . . .
H16 H 0.524 1.1656 1.0321 0.06 Uiso 1 1 calc R . .
C17 C 0.6314(4) 1.2134(6) 1.1155(4) 0.0477(15) Uani 1 1 d . . .
H17 H 0.6005 1.2757 1.145 0.057 Uiso 1 1 calc R . .
C18 C 0.7222(4) 1.1886(6) 1.1396(4) 0.0463(14) Uani 1 1 d . . .
H18 H 0.7542 1.2341 1.1855 0.056 Uiso 1 1 calc R . .
C19 C 0.7664(4) 1.0969(5) 1.0962(4) 0.0368(12) Uani 1 1 d . . .
H19 H 0.8292 1.0812 1.1122 0.044 Uiso 1 1 calc R . .
C20 C 0.7687(4) 0.7737(5) 1.0450(4) 0.0334(11) Uani 1 1 d . . .
C21 C 0.8008(5) 0.6636(5) 0.9932(4) 0.0472(15) Uani 1 1 d . . .
H21A H 0.8667 0.6701 0.9859 0.071 Uiso 1 1 calc R . .
H21B H 0.7677 0.6605 0.9342 0.071 Uiso 1 1 calc R . .
H21C H 0.7885 0.59 1.0266 0.071 Uiso 1 1 calc R . .
C22 C 0.8256(4) 0.7857(6) 1.1330(4) 0.0433(14) Uani 1 1 d . . .
H22A H 0.8225 0.7105 1.1669 0.065 Uiso 1 1 calc R . .
H22B H 0.8018 0.8521 1.1678 0.065 Uiso 1 1 calc R . .
H22C H 0.8894 0.8024 1.121 0.065 Uiso 1 1 calc R . .
C23 C 0.6674(4) 0.7552(6) 1.0628(5) 0.0497(15) Uani 1 1 d . . .
H23A H 0.6608 0.6809 1.0972 0.075 Uiso 1 1 calc R . .
H23B H 0.6309 0.7491 1.0057 0.075 Uiso 1 1 calc R . .
H23C H 0.6458 0.8238 1.097 0.075 Uiso 1 1 calc R . .
N1 N 0.8860(3) 1.1407(4) 0.9178(3) 0.0279(9) Uani 1 1 d . . .
O1 O 0.8024(3) 0.8652(5) 0.7655(3) 0.0481(11) Uani 1 1 d . . .
O2 O 0.7098(2) 0.8807(4) 0.8914(2) 0.0346(8) Uani 1 1 d . . .
P1 P 0.90260(9) 0.88078(13) 0.80502(8) 0.0305(3) Uani 1 1 d . . .
P2 P 0.77866(8) 0.90823(12) 0.97268(8) 0.0254(3) Uani 1 1 d . . .
Ir1 Ir 0.925182(11) 0.959995(16) 0.946354(11) 0.02317(9) Uani 1 1 d . . .
HY1 H 0.764(4) 0.872(5) 0.815(4) 0.028(14) Uiso 1 1 d . . .
HY2 H 0.947(4) 0.999(6) 1.059(4) 0.034(14) Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.143(7) . ?
C1 C2 1.444(8) . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
C3 C6 1.513(9) . ?
C3 C4 1.528(9) . ?
C3 C5 1.546(9) . ?
C3 P1 1.880(6) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C7 C12 1.394(8) . ?
C7 C8 1.397(8) . ?
C7 P1 1.827(6) . ?
C8 C9 1.395(8) . ?
C8 H8 0.95 . ?
C9 C10 1.380(10) . ?
C9 H9 0.95 . ?
C10 C11 1.371(12) . ?
C10 H10 0.95 . ?
C11 C12 1.395(10) . ?
C11 H11 0.95 . ?
C12 H12 0.95 . ?
C14 C19 1.375(8) . ?
C14 C15 1.388(8) . ?
C14 P2 1.825(5) . ?
C15 C16 1.397(9) . ?
C15 H15 0.95 . ?
C16 C17 1.366(10) . ?
C16 H16 0.95 . ?
C17 C18 1.381(9) . ?
C17 H17 0.95 . ?
C18 C19 1.389(8) . ?
C18 H18 0.95 . ?
C19 H19 0.95 . ?
C20 C22 1.516(8) . ?
C20 C21 1.536(8) . ?
C20 C23 1.539(8) . ?
C20 P2 1.854(5) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
N1 Ir1 2.120(4) . ?
O1 P1 1.555(4) . ?
O1 HY1 0.97(6) . ?
O2 P2 1.558(4) . ?
P1 Ir1 2.2930(13) . ?
P2 Ir1 2.2794(12) . ?
Ir1 Ir1 2.7742(4) 3_777 ?
Ir1 HY2 1.75(6) . ?

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 C1 C2 178.6(6) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C6 C3 C4 109.9(6) . . ?
C6 C3 C5 108.6(5) . . ?
C4 C3 C5 109.6(6) . . ?
C6 C3 P1 112.1(4) . . ?
C4 C3 P1 108.3(4) . . ?
C5 C3 P1 108.4(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 118.1(6) . . ?
C12 C7 P1 120.7(5) . . ?
C8 C7 P1 121.1(4) . . ?
C9 C8 C7 120.1(5) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C10 C9 C8 120.9(7) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.6(7) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.1(7) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C7 C12 C11 121.2(6) . . ?
C7 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C19 C14 C15 118.7(5) . . ?
C19 C14 P2 121.9(4) . . ?
C15 C14 P2 119.4(4) . . ?
C14 C15 C16 119.9(6) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.8(5) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 119.7(6) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 119.6(6) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 121.4(5) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C22 C20 C21 109.8(5) . . ?
C22 C20 C23 110.0(5) . . ?
C21 C20 C23 108.1(5) . . ?
C22 C20 P2 112.1(4) . . ?
C21 C20 P2 107.9(4) . . ?
C23 C20 P2 108.8(4) . . ?
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 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C1 N1 Ir1 170.9(4) . . ?
P1 O1 HY1 106(3) . . ?
P2 O2 HY1 106(2) . . ?
O1 P1 C7 104.3(3) . . ?
O1 P1 C3 101.4(3) . . ?
C7 P1 C3 102.5(3) . . ?
O1 P1 Ir1 117.91(16) . . ?
C7 P1 Ir1 111.65(17) . . ?
C3 P1 Ir1 117.1(2) . . ?
O2 P2 C14 102.7(2) . . ?
O2 P2 C20 103.1(2) . . ?
C14 P2 C20 104.8(2) . . ?
O2 P2 Ir1 118.83(15) . . ?
C14 P2 Ir1 111.45(17) . . ?
C20 P2 Ir1 114.48(18) . . ?
N1 Ir1 P2 91.61(11) . . ?
N1 Ir1 P1 98.98(11) . . ?
P2 Ir1 P1 89.01(5) . . ?
N1 Ir1 Ir1 90.38(11) . 3_777 ?
P2 Ir1 Ir1 134.15(3) . 3_777 ?
P1 Ir1 Ir1 135.74(3) . 3_777 ?
N1 Ir1 HY2 89(2) . . ?
P2 Ir1 HY2 90.3(19) . . ?
P1 Ir1 HY2 172(2) . . ?
Ir1 Ir1 HY2 43.9(19) 3_777 . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
