# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_zm14b_0ma
_database_code_depnum_ccdc_archive 'CCDC 1995094'
loop_
_audit_author_name
_audit_author_address
'Lise-Marie Chamoreau'
;Sorbonne Universite, CNRS, IPCM 
France
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2020-11-13 downloaded from the CCDC.
;
_audit_creation_date             2020-10-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 Cl Ir N O'
_chemical_formula_sum            'C19 H23 Cl Ir N O'
_chemical_formula_weight         509.03
_chemical_absolute_configuration ad
_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'
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'
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   10.2639(3)
_cell_length_b                   13.4056(3)
_cell_length_c                   13.9884(4)
_cell_angle_alpha                90
_cell_angle_beta                 110.5530(10)
_cell_angle_gamma                90
_cell_volume                     1802.20(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    200
_cell_measurement_theta_max      32.12
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.560
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6422
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0474 before and 0.0218 after correction. The Ratio of minimum to maximum transmission is 0.8605. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   
;
SADABS, Bruker AXS Inc., Madison,
Wisconsin, USA. or Sheldrick, G. M.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.876
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0179
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18576
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.169
_diffrn_reflns_theta_min         2.608
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.955
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                5984
_reflns_number_total             6195
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_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    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         1.451
_refine_diff_density_min         -0.553
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 2837 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.022(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         6195
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0161
_refine_ls_R_factor_gt           0.0149
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0184P)²+0.6486P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0337
_refine_ls_wR_factor_ref         0.0341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.6361(4) 0.0563(3) 0.2914(3) 0.0262(7) Uani 1 1 d . . . . .
C2 C 0.4987(4) -0.0456(3) 0.3404(3) 0.0315(7) Uani 1 1 d . . . . .
H2A H 0.471838 -0.108971 0.302174 0.038 Uiso 1 1 calc R . . . .
H2B H 0.431337 -0.030290 0.374522 0.038 Uiso 1 1 calc R . . . .
C3 C 0.6469(5) -0.0504(3) 0.4169(3) 0.0380(9) Uani 1 1 d . . . . .
H3A H 0.652748 -0.019885 0.482791 0.046 Uiso 1 1 calc R . . . .
H3B H 0.679704 -0.120254 0.429157 0.046 Uiso 1 1 calc R . . . .
C4 C 0.6719(4) 0.1265(3) 0.2270(3) 0.0264(6) Uani 1 1 d . . . . .
C6 C 0.5784(4) 0.2307(3) 0.0813(3) 0.0308(7) Uani 1 1 d . . . . .
H6 H 0.502299 0.257568 0.026808 0.037 Uiso 1 1 calc R . . . .
C7 C 0.7136(4) 0.2598(3) 0.0925(3) 0.0361(8) Uani 1 1 d . . . . .
H7 H 0.727535 0.306238 0.045747 0.043 Uiso 1 1 calc R . . . .
C8 C 0.8263(4) 0.2227(3) 0.1696(4) 0.0407(9) Uani 1 1 d . . . . .
H8 H 0.917461 0.243397 0.175702 0.049 Uiso 1 1 calc R . . . .
C9 C 0.8080(4) 0.1553(3) 0.2387(3) 0.0354(8) Uani 1 1 d . . . . .
H9 H 0.885514 0.129174 0.292616 0.043 Uiso 1 1 calc R . . . .
C10 C 0.2500(3) 0.2392(3) 0.1325(3) 0.0302(7) Uani 1 1 d . . . . .
C11 C 0.1968(4) 0.1854(3) 0.0378(3) 0.0319(7) Uani 1 1 d . . . . .
C12 C 0.1379(4) 0.0937(3) 0.0582(3) 0.0303(8) Uani 1 1 d . . . . .
C13 C 0.1603(4) 0.0873(3) 0.1638(3) 0.0283(7) Uani 1 1 d . . . . .
C14 C 0.2330(4) 0.1779(3) 0.2110(3) 0.0281(7) Uani 1 1 d . . . . .
C15 C 0.3042(5) 0.3439(3) 0.1459(4) 0.0457(11) Uani 1 1 d . . . . .
H15A H 0.228230 0.390231 0.140753 0.069 Uiso 1 1 calc GR . . . .
H15B H 0.342579 0.359293 0.092509 0.069 Uiso 1 1 calc GR . . . .
H15C H 0.377433 0.350726 0.213056 0.069 Uiso 1 1 calc GR . . . .
C16 C 0.1818(5) 0.2237(5) -0.0661(4) 0.0521(13) Uani 1 1 d . . . . .
H16A H 0.092025 0.257671 -0.095857 0.078 Uiso 1 1 calc GR . . . .
H16B H 0.186205 0.167716 -0.109936 0.078 Uiso 1 1 calc GR . . . .
H16C H 0.257224 0.270673 -0.060457 0.078 Uiso 1 1 calc GR . . . .
C17 C 0.0684(5) 0.0162(4) -0.0199(4) 0.0449(11) Uani 1 1 d . . . . .
H17A H 0.131883 -0.005080 -0.054484 0.067 Uiso 1 1 calc GR . . . .
H17B H -0.016263 0.044103 -0.070126 0.067 Uiso 1 1 calc GR . . . .
H17C H 0.044085 -0.041379 0.013672 0.067 Uiso 1 1 calc GR . . . .
C18 C 0.1170(5) 0.0054(3) 0.2179(4) 0.0414(9) Uani 1 1 d . . . . .
H18A H 0.020011 0.015507 0.212250 0.062 Uiso 1 1 calc GR . . . .
H18B H 0.176728 0.005396 0.290056 0.062 Uiso 1 1 calc GR . . . .
H18C H 0.125725 -0.058705 0.186991 0.062 Uiso 1 1 calc GR . . . .
C19 C 0.2661(5) 0.2052(4) 0.3209(3) 0.0406(9) Uani 1 1 d . . . . .
H19A H 0.333242 0.260176 0.338915 0.061 Uiso 1 1 calc GR . . . .
H19B H 0.306021 0.147256 0.363964 0.061 Uiso 1 1 calc GR . . . .
H19C H 0.180702 0.225865 0.331618 0.061 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.42140(9) -0.03483(7) 0.05585(7) 0.03076(17) Uani 1 1 d . . . . .
Ir1 Ir 0.36660(2) 0.10363(2) 0.14480(2) 0.01991(3) Uani 1 1 d . . . . .
C5 C 0.5527(3) 0.1631(2) 0.1484(3) 0.0239(6) Uani 1 1 d . . . . .
N1 N 0.5072(3) 0.0361(2) 0.2732(2) 0.0233(5) Uani 1 1 d . . . . .
O1 O 0.7291(3) 0.0066(2) 0.3688(2) 0.0397(7) Uani 1 1 d . . . . .


_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 C4 1.437(6) . ?
C1 N1 1.284(5) . ?
C1 O1 1.342(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.523(6) . ?
C2 N1 1.466(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 O1 1.466(5) . ?
C4 C9 1.403(5) . ?
C4 C5 1.415(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.396(5) . ?
C6 C5 1.394(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.369(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.384(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.438(6) . ?
C10 C14 1.430(5) . ?
C10 C15 1.498(6) . ?
C10 Ir1 2.149(4) . ?
C11 C12 1.442(5) . ?
C11 C16 1.497(6) . ?
C11 Ir1 2.156(3) . ?
C12 C13 1.416(6) . ?
C12 C17 1.495(6) . ?
C12 Ir1 2.236(4) . ?
C13 C14 1.457(5) . ?
C13 C18 1.487(5) . ?
C13 Ir1 2.236(3) . ?
C14 C19 1.498(6) . ?
C14 Ir1 2.150(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Cl1 Ir1 2.4085(9) . ?
Ir1 C5 2.055(3) . ?
Ir1 N1 2.076(3) . ?

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 C4 119.1(3) . . ?
N1 C1 O1 116.6(4) . . ?
O1 C1 C4 124.4(3) . . ?
H2A C2 H2B 109.2 . . ?
C3 C2 H2A 111.3 . . ?
C3 C2 H2B 111.3 . . ?
N1 C2 H2A 111.3 . . ?
N1 C2 H2B 111.3 . . ?
N1 C2 C3 102.3(3) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
O1 C3 C2 104.4(3) . . ?
O1 C3 H3A 110.9 . . ?
O1 C3 H3B 110.9 . . ?
C9 C4 C1 124.8(4) . . ?
C9 C4 C5 123.3(4) . . ?
C5 C4 C1 111.9(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.3(4) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(3) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 120.9 . . ?
C8 C9 C4 118.2(4) . . ?
C8 C9 H9 120.9 . . ?
C11 C10 C15 126.1(4) . . ?
C11 C10 Ir1 70.7(2) . . ?
C14 C10 C11 108.1(3) . . ?
C14 C10 C15 125.6(4) . . ?
C14 C10 Ir1 70.6(2) . . ?
C15 C10 Ir1 127.6(3) . . ?
C10 C11 C12 107.2(3) . . ?
C10 C11 C16 126.8(4) . . ?
C10 C11 Ir1 70.25(19) . . ?
C12 C11 C16 125.2(4) . . ?
C12 C11 Ir1 73.9(2) . . ?
C16 C11 Ir1 129.1(3) . . ?
C11 C12 C17 125.0(4) . . ?
C11 C12 Ir1 67.85(19) . . ?
C13 C12 C11 109.4(3) . . ?
C13 C12 C17 125.5(4) . . ?
C13 C12 Ir1 71.5(2) . . ?
C17 C12 Ir1 125.3(3) . . ?
C12 C13 C14 107.0(3) . . ?
C12 C13 C18 127.4(4) . . ?
C12 C13 Ir1 71.5(2) . . ?
C14 C13 C18 125.6(4) . . ?
C14 C13 Ir1 67.44(19) . . ?
C18 C13 Ir1 126.7(3) . . ?
C10 C14 C13 108.2(3) . . ?
C10 C14 C19 127.1(4) . . ?
C10 C14 Ir1 70.5(2) . . ?
C13 C14 C19 124.3(4) . . ?
C13 C14 Ir1 73.8(2) . . ?
C19 C14 Ir1 127.3(3) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 Ir1 C11 39.02(15) . . ?
C10 Ir1 C12 63.75(14) . . ?
C10 Ir1 C13 64.42(14) . . ?
C10 Ir1 C14 38.86(14) . . ?
C10 Ir1 Cl1 146.58(11) . . ?
C11 Ir1 C12 38.27(14) . . ?
C11 Ir1 C13 64.15(14) . . ?
C11 Ir1 Cl1 108.14(11) . . ?
C12 Ir1 Cl1 93.74(11) . . ?
C13 Ir1 C12 36.93(14) . . ?
C13 Ir1 Cl1 112.88(10) . . ?
C14 Ir1 C11 65.24(14) . . ?
C14 Ir1 C12 63.50(14) . . ?
C14 Ir1 C13 38.74(14) . . ?
C14 Ir1 Cl1 151.58(10) . . ?
C5 Ir1 C10 99.23(13) . . ?
C5 Ir1 C11 109.72(14) . . ?
C5 Ir1 C12 145.74(14) . . ?
C5 Ir1 C13 161.18(14) . . ?
C5 Ir1 C14 122.54(13) . . ?
C5 Ir1 Cl1 85.87(9) . . ?
C5 Ir1 N1 77.89(13) . . ?
N1 Ir1 C10 129.52(13) . . ?
N1 Ir1 C11 165.84(13) . . ?
N1 Ir1 C12 136.21(13) . . ?
N1 Ir1 C13 104.73(13) . . ?
N1 Ir1 C14 100.62(12) . . ?
N1 Ir1 Cl1 83.89(8) . . ?
C4 C5 Ir1 115.2(2) . . ?
C6 C5 C4 115.6(3) . . ?
C6 C5 Ir1 129.0(3) . . ?
C1 N1 C2 108.6(3) . . ?
C1 N1 Ir1 115.8(2) . . ?
C2 N1 Ir1 134.5(2) . . ?
C1 O1 C3 105.5(3) . . ?

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'
