# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_11_sq
_database_code_depnum_ccdc_archive 'CCDC 1527325'
_audit_update_record             
;
2017-01-13 deposited with the CCDC.
2017-02-17 downloaded from the CCDC.
;
_audit_creation_date             2017-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5289)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H23 Ir N3 O'
_chemical_formula_sum            'C32 H23 Ir N3 O'
_chemical_formula_weight         657.73
_chemical_melting_point          ?
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'
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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.434(5)
_cell_length_b                   14.581(5)
_cell_length_c                   18.230(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.210(5)
_cell_angle_gamma                90
_cell_volume                     2981.3(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.974
_cell_measurement_theta_min      2.711
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.505
_exptl_absorpt_correction_T_max  0.509
_exptl_absorpt_correction_T_min  0.404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            60997
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.240
_diffrn_reflns_theta_max         28.358
_diffrn_reflns_theta_min         2.972
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'APEX II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5597
_reflns_number_total             7398
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         2.037
_refine_diff_density_min         -1.496
_refine_diff_density_rms         0.109
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         7398
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+6.1991P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0609
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C12(H12),
 C13(H13), C14(H14), C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24),
  C25(H25), C26(H26), C27(H27), C29(H29), C31(H31), C32(H32)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir -0.12246(2) 0.22489(2) 0.35584(2) 0.02796(5) Uani 1 1 d . . . . .
O1 O -0.0057(3) 0.29412(18) 0.29493(15) 0.0420(7) Uani 1 1 d . . . . .
N1 N -0.2034(3) 0.1650(2) 0.25793(16) 0.0328(7) Uani 1 1 d . . . . .
N2 N -0.0554(3) 0.2858(2) 0.45570(16) 0.0325(7) Uani 1 1 d . . . . .
N3 N 0.0181(3) 0.1258(2) 0.38505(15) 0.0284(6) Uani 1 1 d . . . . .
C1 C -0.1704(4) 0.0854(3) 0.2312(2) 0.0428(10) Uani 1 1 d . . . . .
H1 H -0.102152 0.056462 0.256965 0.051 Uiso 1 1 calc R . . . .
C2 C -0.2326(5) 0.0448(3) 0.1679(3) 0.0599(13) Uani 1 1 d . . . . .
H2 H -0.207339 -0.010845 0.151412 0.072 Uiso 1 1 calc R . . . .
C3 C -0.3335(5) 0.0877(4) 0.1289(3) 0.0695(15) Uani 1 1 d . . . . .
H3 H -0.377787 0.061161 0.085964 0.083 Uiso 1 1 calc R . . . .
C4 C -0.3670(4) 0.1698(4) 0.1546(3) 0.0594(13) Uani 1 1 d . . . . .
H4 H -0.434686 0.199385 0.128746 0.071 Uiso 1 1 calc R . . . .
C5 C -0.3012(4) 0.2099(3) 0.2190(2) 0.0399(9) Uani 1 1 d . . . . .
C6 C -0.3259(4) 0.2967(3) 0.2530(2) 0.0389(9) Uani 1 1 d . . . . .
C7 C -0.4159(4) 0.3571(3) 0.2194(3) 0.0533(12) Uani 1 1 d . . . . .
H7 H -0.464426 0.342244 0.173906 0.064 Uiso 1 1 calc R . . . .
C8 C -0.4320(5) 0.4386(4) 0.2543(3) 0.0639(14) Uani 1 1 d . . . . .
H8 H -0.491435 0.478963 0.232197 0.077 Uiso 1 1 calc R . . . .
C9 C -0.3603(4) 0.4605(3) 0.3218(3) 0.0586(13) Uani 1 1 d . . . . .
H9 H -0.371736 0.515559 0.345223 0.070 Uiso 1 1 calc R . . . .
C10 C -0.2714(4) 0.4011(3) 0.3549(3) 0.0457(10) Uani 1 1 d . . . . .
H10 H -0.224173 0.416712 0.400679 0.055 Uiso 1 1 calc R . . . .
C11 C -0.2508(3) 0.3179(3) 0.3211(2) 0.0339(8) Uani 1 1 d . . . . .
C12 C 0.0305(4) 0.3498(3) 0.4659(3) 0.0476(11) Uani 1 1 d . . . . .
H12 H 0.060895 0.369942 0.425008 0.057 Uiso 1 1 calc R . . . .
C13 C 0.0747(5) 0.3862(4) 0.5349(3) 0.0670(15) Uani 1 1 d . . . . .
H13 H 0.133647 0.431000 0.540473 0.080 Uiso 1 1 calc R . . . .
C14 C 0.0314(5) 0.3561(4) 0.5959(3) 0.0682(15) Uani 1 1 d . . . . .
H14 H 0.061530 0.379469 0.643214 0.082 Uiso 1 1 calc R . . . .
C15 C -0.0569(5) 0.2911(4) 0.5860(2) 0.0575(13) Uani 1 1 d . . . . .
H15 H -0.086864 0.270506 0.626944 0.069 Uiso 1 1 calc R . . . .
C16 C -0.1023(4) 0.2555(3) 0.5149(2) 0.0393(10) Uani 1 1 d . . . . .
C17 C -0.1954(4) 0.1881(3) 0.4957(2) 0.0400(9) Uani 1 1 d . . . . .
C18 C -0.2521(5) 0.1450(4) 0.5478(3) 0.0592(13) Uani 1 1 d . . . . .
H18 H -0.228604 0.158104 0.598500 0.071 Uiso 1 1 calc R . . . .
C19 C -0.3420(5) 0.0839(4) 0.5244(3) 0.0768(17) Uani 1 1 d . . . . .
H19 H -0.378417 0.054201 0.559142 0.092 Uiso 1 1 calc R . . . .
C20 C -0.3786(5) 0.0661(4) 0.4491(3) 0.0714(16) Uani 1 1 d . . . . .
H20 H -0.441723 0.025992 0.433340 0.086 Uiso 1 1 calc R . . . .
C21 C -0.3229(4) 0.1072(3) 0.3970(3) 0.0509(11) Uani 1 1 d . . . . .
H21 H -0.349483 0.094366 0.346516 0.061 Uiso 1 1 calc R . . . .
C22 C -0.2275(3) 0.1676(3) 0.4184(2) 0.0343(8) Uani 1 1 d . . . . .
C23 C 0.0944(3) 0.2655(3) 0.2794(2) 0.0335(8) Uani 1 1 d . . . . .
C24 C 0.1486(4) 0.3202(3) 0.2306(2) 0.0481(11) Uani 1 1 d . . . . .
H24 H 0.111699 0.374416 0.211718 0.058 Uiso 1 1 calc R . . . .
C25 C 0.2523(5) 0.2956(4) 0.2110(3) 0.0639(15) Uani 1 1 d . . . . .
H25 H 0.284530 0.332774 0.178524 0.077 Uiso 1 1 calc R . . . .
C26 C 0.3118(5) 0.2160(4) 0.2384(3) 0.0698(16) Uani 1 1 d . . . . .
H26 H 0.383457 0.199893 0.224958 0.084 Uiso 1 1 calc R . . . .
C27 C 0.2626(4) 0.1616(3) 0.2858(3) 0.0523(12) Uani 1 1 d . . . . .
H27 H 0.301765 0.108052 0.304245 0.063 Uiso 1 1 calc R . . . .
C28 C 0.1547(3) 0.1844(3) 0.3073(2) 0.0349(8) Uani 1 1 d . . . . .
C29 C 0.1163(3) 0.1237(3) 0.3603(2) 0.0337(8) Uani 1 1 d . . . . .
H29 H 0.169121 0.077037 0.379166 0.040 Uiso 1 1 calc R . . . .
C30 C 0.0102(3) 0.0606(2) 0.44328(19) 0.0293(8) Uani 1 1 d . . . . .
C31 C 0.0819(3) 0.0700(3) 0.5132(2) 0.0339(8) Uani 1 1 d . . . . .
H31 H 0.136888 0.117690 0.522152 0.041 Uiso 1 1 calc R . . . .
C32 C 0.0726(3) 0.0090(2) 0.5698(2) 0.0330(8) Uani 1 1 d . . . . .
H32 H 0.122038 0.015016 0.616478 0.040 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 O1 2.147(3) . ?
Ir1 N1 2.040(3) . ?
Ir1 N2 2.036(3) . ?
Ir1 N3 2.150(3) . ?
Ir1 C11 2.008(4) . ?
Ir1 C22 1.992(4) . ?
O1 C23 1.300(5) . ?
N1 C1 1.341(5) . ?
N1 C5 1.369(5) . ?
N2 C12 1.341(5) . ?
N2 C16 1.369(5) . ?
N3 C29 1.288(4) . ?
N3 C30 1.441(4) . ?
C1 C2 1.367(6) . ?
C2 C3 1.382(7) . ?
C3 C4 1.368(7) . ?
C4 C5 1.393(6) . ?
C5 C6 1.460(6) . ?
C6 C7 1.402(6) . ?
C6 C11 1.399(5) . ?
C7 C8 1.377(7) . ?
C8 C9 1.377(7) . ?
C9 C10 1.381(6) . ?
C10 C11 1.402(6) . ?
C12 C13 1.367(6) . ?
C13 C14 1.374(8) . ?
C14 C15 1.370(7) . ?
C15 C16 1.398(6) . ?
C16 C17 1.441(6) . ?
C17 C18 1.400(6) . ?
C17 C22 1.417(5) . ?
C18 C19 1.365(7) . ?
C19 C20 1.379(8) . ?
C20 C21 1.380(6) . ?
C21 C22 1.398(6) . ?
C23 C24 1.424(5) . ?
C23 C28 1.413(5) . ?
C24 C25 1.352(6) . ?
C25 C26 1.388(7) . ?
C26 C27 1.371(6) . ?
C27 C28 1.404(6) . ?
C28 C29 1.441(5) . ?
C30 C31 1.382(5) . ?
C30 C32 1.377(5) 3_556 ?
C31 C32 1.382(5) . ?

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
O1 Ir1 N3 86.21(11) . . ?
N1 Ir1 O1 88.32(12) . . ?
N1 Ir1 N3 96.85(12) . . ?
N2 Ir1 O1 95.36(12) . . ?
N2 Ir1 N1 175.23(12) . . ?
N2 Ir1 N3 86.44(11) . . ?
C11 Ir1 O1 90.52(13) . . ?
C11 Ir1 N1 80.41(14) . . ?
C11 Ir1 N2 96.50(14) . . ?
C11 Ir1 N3 175.80(12) . . ?
C22 Ir1 O1 175.72(13) . . ?
C22 Ir1 N1 95.73(14) . . ?
C22 Ir1 N2 80.53(14) . . ?
C22 Ir1 N3 94.67(13) . . ?
C22 Ir1 C11 88.79(15) . . ?
C23 O1 Ir1 128.6(2) . . ?
C1 N1 Ir1 125.2(3) . . ?
C1 N1 C5 119.0(3) . . ?
C5 N1 Ir1 115.8(3) . . ?
C12 N2 Ir1 124.5(3) . . ?
C12 N2 C16 120.2(3) . . ?
C16 N2 Ir1 115.3(3) . . ?
C29 N3 Ir1 126.1(2) . . ?
C29 N3 C30 115.2(3) . . ?
C30 N3 Ir1 118.3(2) . . ?
N1 C1 C2 123.0(4) . . ?
C1 C2 C3 118.9(5) . . ?
C4 C3 C2 118.8(4) . . ?
C3 C4 C5 120.9(5) . . ?
N1 C5 C4 119.3(4) . . ?
N1 C5 C6 113.6(3) . . ?
C4 C5 C6 127.1(4) . . ?
C7 C6 C5 123.1(4) . . ?
C11 C6 C5 115.6(4) . . ?
C11 C6 C7 121.3(4) . . ?
C8 C7 C6 119.6(4) . . ?
C7 C8 C9 120.2(5) . . ?
C8 C9 C10 120.3(5) . . ?
C9 C10 C11 121.5(4) . . ?
C6 C11 Ir1 114.5(3) . . ?
C6 C11 C10 117.1(4) . . ?
C10 C11 Ir1 128.4(3) . . ?
N2 C12 C13 121.9(4) . . ?
C12 C13 C14 119.5(5) . . ?
C15 C14 C13 119.1(4) . . ?
C14 C15 C16 120.7(5) . . ?
N2 C16 C15 118.6(4) . . ?
N2 C16 C17 114.3(3) . . ?
C15 C16 C17 127.1(4) . . ?
C18 C17 C16 123.9(4) . . ?
C18 C17 C22 121.1(4) . . ?
C22 C17 C16 114.9(3) . . ?
C19 C18 C17 120.0(5) . . ?
C18 C19 C20 119.9(4) . . ?
C19 C20 C21 120.8(5) . . ?
C20 C21 C22 121.4(4) . . ?
C17 C22 Ir1 114.4(3) . . ?
C21 C22 Ir1 129.0(3) . . ?
C21 C22 C17 116.5(4) . . ?
O1 C23 C24 117.7(4) . . ?
O1 C23 C28 125.4(3) . . ?
C28 C23 C24 116.9(4) . . ?
C25 C24 C23 121.8(4) . . ?
C24 C25 C26 121.3(4) . . ?
C27 C26 C25 118.6(4) . . ?
C26 C27 C28 122.0(5) . . ?
C23 C28 C29 124.3(3) . . ?
C27 C28 C23 119.4(4) . . ?
C27 C28 C29 116.2(4) . . ?
N3 C29 C28 128.3(4) . . ?
C31 C30 N3 120.1(3) . . ?
C32 C30 N3 119.9(3) 3_556 . ?
C32 C30 C31 119.9(3) 3_556 . ?
C30 C31 C32 120.4(3) . . ?
C30 C32 C31 119.7(3) 3_556 . ?

_olex2_submission_special_instructions 'No special instructions were received'
