# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_2
_audit_block_doi                 10.5517/ccdc.csd.cc131q84
_database_code_depnum_ccdc_archive 'CCDC 1014545'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/jacs.6b01249 2016
_audit_update_record             
;
2014-07-17 deposited with the CCDC.
2017-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.40 H5 B2 Ir0.20 S0.40'
_chemical_formula_weight         106.75

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'
B B 0.0013 0.0007 '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           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   11.8131(10)
_cell_length_b                   12.9608(11)
_cell_length_c                   26.409(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4043.4(6)
_cell_formula_units_Z            40
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2048
_exptl_absorpt_coefficient_mu    6.803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.154
_exptl_absorpt_correction_T_max  0.224
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27672
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3915
_reflns_number_gt                2871
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0282P)²+0.9780P] 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         3915
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.001

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 0.582877(15) 0.877141(14) 0.848382(6) 0.02872(7) Uani 1 1 d . . .
S2 S 0.50741(11) 0.71766(9) 0.83324(4) 0.0377(3) Uani 1 1 d . . .
S1 S 0.49901(11) 0.89854(9) 0.92645(4) 0.0347(3) Uani 1 1 d . . .
C17 C 0.7173(4) 0.8808(4) 0.79184(18) 0.0383(12) Uani 1 1 d . . .
C15 C 0.6015(4) 1.0218(4) 0.80957(18) 0.0363(12) Uani 1 1 d . . .
C14 C 0.6856(4) 1.0178(4) 0.84873(17) 0.0365(12) Uani 1 1 d . . .
B9 B 0.4029(4) 0.7872(4) 0.93381(18) 0.0269(11) Uani 1 1 d . . .
B12 B 0.4068(4) 0.6938(4) 0.8855(2) 0.0309(12) Uani 1 1 d . . .
B7 B 0.2689(5) 0.6394(4) 0.8785(2) 0.0431(15) Uani 1 1 d . . .
H7 H 0.2370 0.6109 0.8420 0.052 Uiso 1 1 calc R . .
C16 C 0.6226(4) 0.9393(4) 0.77422(17) 0.0377(12) Uani 1 1 d . . .
C13 C 0.7542(4) 0.9290(4) 0.83900(17) 0.0343(11) Uani 1 1 d . . .
B3 B 0.3512(5) 0.5896(4) 0.9785(2) 0.0396(14) Uani 1 1 d . . .
H3 H 0.3697 0.5292 1.0066 0.048 Uiso 1 1 calc R . .
C18 C 0.8523(4) 0.8968(4) 0.8707(2) 0.0535(15) Uani 1 1 d . . .
H18A H 0.9170 0.9382 0.8623 0.080 Uiso 1 1 calc R . .
H18B H 0.8691 0.8255 0.8644 0.080 Uiso 1 1 calc R . .
H18C H 0.8340 0.9060 0.9058 0.080 Uiso 1 1 calc R . .
B4 B 0.3681(5) 0.7235(4) 0.9922(2) 0.0392(14) Uani 1 1 d . . .
H4 H 0.3992 0.7510 1.0290 0.047 Uiso 1 1 calc R . .
B10 B 0.4570(5) 0.6599(4) 0.9476(2) 0.0329(13) Uani 1 1 d . . .
H10 H 0.5471 0.6456 0.9555 0.039 Uiso 1 1 calc R . .
C22 C 0.7661(5) 0.7886(5) 0.7668(2) 0.0586(16) Uani 1 1 d . . .
H22A H 0.7067 0.7496 0.7510 0.088 Uiso 1 1 calc R . .
H22B H 0.8035 0.7465 0.7916 0.088 Uiso 1 1 calc R . .
H22C H 0.8197 0.8100 0.7416 0.088 Uiso 1 1 calc R . .
B5 B 0.2604(5) 0.7920(4) 0.9579(2) 0.0420(15) Uani 1 1 d . . .
H5 H 0.2223 0.8631 0.9729 0.050 Uiso 1 1 calc R . .
C21 C 0.5590(5) 0.9212(5) 0.7262(2) 0.0606(17) Uani 1 1 d . . .
H21A H 0.5947 0.9583 0.6991 0.091 Uiso 1 1 calc R . .
H21B H 0.4825 0.9448 0.7301 0.091 Uiso 1 1 calc R . .
H21C H 0.5589 0.8488 0.7186 0.091 Uiso 1 1 calc R . .
B8 B 0.2837(4) 0.7718(5) 0.8927(2) 0.0389(14) Uani 1 1 d . . .
H8 H 0.2608 0.8311 0.8647 0.047 Uiso 1 1 calc R . .
C20 C 0.5090(5) 1.1000(4) 0.8039(2) 0.0587(16) Uani 1 1 d . . .
H20A H 0.5001 1.1372 0.8351 0.088 Uiso 1 1 calc R . .
H20B H 0.4394 1.0656 0.7956 0.088 Uiso 1 1 calc R . .
H20C H 0.5283 1.1473 0.7773 0.088 Uiso 1 1 calc R . .
C19 C 0.7003(5) 1.0906(4) 0.8924(2) 0.0544(16) Uani 1 1 d . . .
H19A H 0.7193 1.0522 0.9223 0.082 Uiso 1 1 calc R . .
H19B H 0.6310 1.1277 0.8980 0.082 Uiso 1 1 calc R . .
H19C H 0.7599 1.1385 0.8849 0.082 Uiso 1 1 calc R . .
C2 C 0.2424(4) 0.5857(4) 0.9361(2) 0.0422(13) Uani 1 1 d . . .
H2 H 0.1870 0.5176 0.9372 0.051 Uiso 1 1 calc R . .
C1 C 0.2387(4) 0.6720(4) 0.9815(2) 0.0437(13) Uani 1 1 d . . .
H1 H 0.1818 0.6638 1.0142 0.052 Uiso 1 1 calc R . .
B6 B 0.1786(5) 0.7020(5) 0.9237(2) 0.0502(17) Uani 1 1 d . . .
H6 H 0.0876 0.7134 0.9168 0.060 Uiso 1 1 calc R . .
B11 B 0.3747(5) 0.5712(4) 0.9132(2) 0.0386(14) Uani 1 1 d . . .
H11 H 0.4102 0.4985 0.8987 0.046 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 C13 2.147(5) . ?
Ir1 C15 2.148(4) . ?
Ir1 C16 2.169(4) . ?
Ir1 C17 2.180(5) . ?
Ir1 C14 2.189(5) . ?
Ir1 S2 2.2863(12) . ?
Ir1 S1 2.3041(12) . ?
S2 B12 1.848(5) . ?
S1 B9 1.846(5) . ?
C17 C16 1.429(7) . ?
C17 C13 1.460(6) . ?
C17 C22 1.482(7) . ?
C15 C14 1.435(6) . ?
C15 C16 1.441(7) . ?
C15 C20 1.498(7) . ?
C14 C13 1.431(7) . ?
C14 C19 1.501(6) . ?
B9 B12 1.759(7) . ?
B9 B8 1.789(7) . ?
B9 B4 1.796(7) . ?
B9 B5 1.801(7) . ?
B9 B10 1.806(7) . ?
B12 B8 1.781(8) . ?
B12 B7 1.785(7) . ?
B12 B11 1.789(8) . ?
B12 B10 1.797(7) . ?
B7 C2 1.703(8) . ?
B7 B8 1.766(8) . ?
B7 B11 1.784(8) . ?
B7 B6 1.794(9) . ?
C16 C21 1.492(6) . ?
C13 C18 1.489(7) . ?
B3 C2 1.704(8) . ?
B3 C1 1.706(8) . ?
B3 B10 1.749(8) . ?
B3 B11 1.762(8) . ?
B3 B4 1.784(8) . ?
B4 C1 1.691(8) . ?
B4 B10 1.780(8) . ?
B4 B5 1.795(9) . ?
B10 B11 1.759(8) . ?
B5 C1 1.695(7) . ?
B5 B8 1.762(8) . ?
B5 B6 1.764(9) . ?
B8 B6 1.740(8) . ?
C2 C1 1.638(7) . ?
C2 B11 1.686(7) . ?
C2 B6 1.717(8) . ?
C1 B6 1.728(8) . ?

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
C13 Ir1 C15 64.86(18) . . ?
C13 Ir1 C16 64.89(18) . . ?
C15 Ir1 C16 39.00(18) . . ?
C13 Ir1 C17 39.42(17) . . ?
C15 Ir1 C17 65.14(18) . . ?
C16 Ir1 C17 38.37(18) . . ?
C13 Ir1 C14 38.51(18) . . ?
C15 Ir1 C14 38.62(17) . . ?
C16 Ir1 C14 64.84(17) . . ?
C17 Ir1 C14 65.24(18) . . ?
C13 Ir1 S2 129.08(14) . . ?
C15 Ir1 S2 138.21(14) . . ?
C16 Ir1 S2 105.20(14) . . ?
C17 Ir1 S2 100.60(13) . . ?
C14 Ir1 S2 165.79(13) . . ?
C13 Ir1 S1 118.10(13) . . ?
C15 Ir1 S1 111.46(14) . . ?
C16 Ir1 S1 148.90(15) . . ?
C17 Ir1 S1 157.43(14) . . ?
C14 Ir1 S1 97.72(12) . . ?
S2 Ir1 S1 95.60(4) . . ?
B12 S2 Ir1 105.76(17) . . ?
B9 S1 Ir1 105.34(16) . . ?
C16 C17 C13 106.5(4) . . ?
C16 C17 C22 125.9(5) . . ?
C13 C17 C22 127.5(5) . . ?
C16 C17 Ir1 70.4(3) . . ?
C13 C17 Ir1 69.1(3) . . ?
C22 C17 Ir1 124.8(3) . . ?
C14 C15 C16 108.7(4) . . ?
C14 C15 C20 127.0(5) . . ?
C16 C15 C20 124.3(5) . . ?
C14 C15 Ir1 72.3(3) . . ?
C16 C15 Ir1 71.3(3) . . ?
C20 C15 Ir1 124.3(3) . . ?
C13 C14 C15 107.0(4) . . ?
C13 C14 C19 125.3(5) . . ?
C15 C14 C19 127.7(5) . . ?
C13 C14 Ir1 69.1(3) . . ?
C15 C14 Ir1 69.1(3) . . ?
C19 C14 Ir1 126.2(3) . . ?
B12 B9 B8 60.3(3) . . ?
B12 B9 B4 108.1(4) . . ?
B8 B9 B4 106.8(4) . . ?
B12 B9 B5 107.7(4) . . ?
B8 B9 B5 58.8(3) . . ?
B4 B9 B5 59.9(3) . . ?
B12 B9 B10 60.5(3) . . ?
B8 B9 B10 107.4(4) . . ?
B4 B9 B10 59.2(3) . . ?
B5 B9 B10 106.9(4) . . ?
B12 B9 S1 116.5(3) . . ?
B8 B9 S1 120.5(3) . . ?
B4 B9 S1 126.2(3) . . ?
B5 B9 S1 125.8(3) . . ?
B10 B9 S1 121.2(3) . . ?
B9 B12 B8 60.7(3) . . ?
B9 B12 B7 108.9(4) . . ?
B8 B12 B7 59.4(3) . . ?
B9 B12 B11 108.0(4) . . ?
B8 B12 B11 106.7(4) . . ?
B7 B12 B11 59.9(3) . . ?
B9 B12 B10 61.0(3) . . ?
B8 B12 B10 108.1(4) . . ?
B7 B12 B10 107.5(4) . . ?
B11 B12 B10 58.7(3) . . ?
B9 B12 S2 116.3(3) . . ?
B8 B12 S2 120.6(4) . . ?
B7 B12 S2 125.1(4) . . ?
B11 B12 S2 126.2(4) . . ?
B10 B12 S2 120.7(3) . . ?
C2 B7 B8 103.0(4) . . ?
C2 B7 B12 103.6(4) . . ?
B8 B7 B12 60.2(3) . . ?
C2 B7 B11 57.8(3) . . ?
B8 B7 B11 107.6(4) . . ?
B12 B7 B11 60.2(3) . . ?
C2 B7 B6 58.7(3) . . ?
B8 B7 B6 58.5(3) . . ?
B12 B7 B6 107.2(4) . . ?
B11 B7 B6 107.4(4) . . ?
C17 C16 C15 108.5(4) . . ?
C17 C16 C21 126.0(5) . . ?
C15 C16 C21 125.4(5) . . ?
C17 C16 Ir1 71.2(3) . . ?
C15 C16 Ir1 69.7(2) . . ?
C21 C16 Ir1 126.9(3) . . ?
C14 C13 C17 109.2(4) . . ?
C14 C13 C18 124.4(5) . . ?
C17 C13 C18 126.3(5) . . ?
C14 C13 Ir1 72.3(3) . . ?
C17 C13 Ir1 71.5(3) . . ?
C18 C13 Ir1 125.5(3) . . ?
C2 B3 C1 57.4(3) . . ?
C2 B3 B10 104.4(4) . . ?
C1 B3 B10 104.6(4) . . ?
C2 B3 B11 58.2(3) . . ?
C1 B3 B11 104.6(4) . . ?
B10 B3 B11 60.1(3) . . ?
C2 B3 B4 104.2(4) . . ?
C1 B3 B4 57.9(3) . . ?
B10 B3 B4 60.5(3) . . ?
B11 B3 B4 108.2(4) . . ?
C1 B4 B10 103.9(4) . . ?
C1 B4 B3 58.7(3) . . ?
B10 B4 B3 58.8(3) . . ?
C1 B4 B9 104.2(4) . . ?
B10 B4 B9 60.7(3) . . ?
B3 B4 B9 107.4(4) . . ?
C1 B4 B5 58.1(3) . . ?
B10 B4 B5 108.3(4) . . ?
B3 B4 B5 107.4(4) . . ?
B9 B4 B5 60.2(3) . . ?
B3 B10 B11 60.3(3) . . ?
B3 B10 B4 60.7(3) . . ?
B11 B10 B4 108.5(4) . . ?
B3 B10 B12 108.4(4) . . ?
B11 B10 B12 60.4(3) . . ?
B4 B10 B12 107.1(4) . . ?
B3 B10 B9 108.5(4) . . ?
B11 B10 B9 107.3(4) . . ?
B4 B10 B9 60.1(3) . . ?
B12 B10 B9 58.4(3) . . ?
C1 B5 B8 104.2(4) . . ?
C1 B5 B6 59.9(3) . . ?
B8 B5 B6 59.1(3) . . ?
C1 B5 B4 57.9(3) . . ?
B8 B5 B4 107.9(4) . . ?
B6 B5 B4 108.6(4) . . ?
C1 B5 B9 103.8(4) . . ?
B8 B5 B9 60.3(3) . . ?
B6 B5 B9 108.0(4) . . ?
B4 B5 B9 59.9(3) . . ?
B6 B8 B5 60.5(3) . . ?
B6 B8 B7 61.6(3) . . ?
B5 B8 B7 109.7(4) . . ?
B6 B8 B12 109.7(4) . . ?
B5 B8 B12 108.4(4) . . ?
B7 B8 B12 60.4(3) . . ?
B6 B8 B9 109.6(4) . . ?
B5 B8 B9 60.9(3) . . ?
B7 B8 B9 108.4(4) . . ?
B12 B8 B9 59.0(3) . . ?
C1 C2 B11 111.3(4) . . ?
C1 C2 B7 112.3(4) . . ?
B11 C2 B7 63.5(3) . . ?
C1 C2 B3 61.4(3) . . ?
B11 C2 B3 62.6(3) . . ?
B7 C2 B3 115.9(4) . . ?
C1 C2 B6 61.9(3) . . ?
B11 C2 B6 115.9(4) . . ?
B7 C2 B6 63.3(3) . . ?
B3 C2 B6 115.6(4) . . ?
C2 C1 B4 111.5(4) . . ?
C2 C1 B5 110.7(4) . . ?
B4 C1 B5 64.1(3) . . ?
C2 C1 B3 61.2(3) . . ?
B4 C1 B3 63.3(3) . . ?
B5 C1 B3 116.1(4) . . ?
C2 C1 B6 61.3(3) . . ?
B4 C1 B6 115.5(4) . . ?
B5 C1 B6 62.1(3) . . ?
B3 C1 B6 114.9(4) . . ?
C2 B6 C1 56.8(3) . . ?
C2 B6 B8 103.5(4) . . ?
C1 B6 B8 103.8(4) . . ?
C2 B6 B5 103.9(4) . . ?
C1 B6 B5 58.0(3) . . ?
B8 B6 B5 60.4(3) . . ?
C2 B6 B7 58.0(3) . . ?
C1 B6 B7 103.9(4) . . ?
B8 B6 B7 59.9(3) . . ?
B5 B6 B7 108.3(4) . . ?
C2 B11 B10 104.7(4) . . ?
C2 B11 B3 59.2(3) . . ?
B10 B11 B3 59.6(3) . . ?
C2 B11 B7 58.7(3) . . ?
B10 B11 B7 109.2(4) . . ?
B3 B11 B7 109.0(4) . . ?
C2 B11 B12 104.1(4) . . ?
B10 B11 B12 60.9(3) . . ?
B3 B11 B12 108.2(4) . . ?
B7 B11 B12 59.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.106
