# 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. 
# 
#######################################################################

data_17091
_database_code_depnum_ccdc_archive 'CCDC 1959427'
_audit_update_record             
;
2020-02-04 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 Cl F3 Ir N'
_chemical_formula_sum            'C22 H22 Cl F3 Ir N'
_chemical_formula_weight         585.05

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   15.581(8)
_cell_length_b                   7.767(4)
_cell_length_c                   16.411(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.502(8)
_cell_angle_gamma                90
_cell_volume                     1984.3(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    825
_cell_measurement_theta_min      2.902
_cell_measurement_theta_max      28.162

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    6.898
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.478
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   
;
absoprtion correction based on 6957 reflections(SADABS);Rint 0.1340 before
correction and 0.0708 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14362
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_av_R_equivalents  0.1116
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.308
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3910
_reflns_number_gt                3082
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3910
_refine_ls_number_parameters     285
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.0959
_refine_ls_wR_factor_gt          0.0904
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_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_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 0.71075(2) 0.05555(4) 0.18942(2) 0.01803(11) Uani 1 1 d . . . . .
Cl1 Cl 0.63901(13) -0.2138(2) 0.16023(12) 0.0251(4) Uani 1 1 d . . . . .
F1A F 0.9787(17) -0.209(2) 0.0139(13) 0.059(6) Uani 0.5 1 d . . P A 1
F1B F 0.9797(16) -0.291(3) 0.0227(14) 0.057(5) Uani 0.5 1 d . U P A 2
F2A F 1.0821(10) -0.138(3) 0.0916(10) 0.065(4) Uani 0.5 1 d . U P A 1
F2B F 1.0534(9) -0.0833(14) 0.0693(10) 0.048(4) Uani 0.5 1 d D U P A 2
F3A F 1.0805(7) -0.3372(17) 0.1080(6) 0.053(3) Uani 0.6 1 d . U P A 1
F3B F 1.0333(13) -0.401(2) 0.0838(11) 0.061(4) Uani 0.4 1 d . U P A 2
N1 N 0.7123(4) -0.0212(7) 0.3118(4) 0.0185(14) Uani 1 1 d . . . . .
C1 C 0.6458(6) 0.0061(11) 0.3607(5) 0.030(2) Uani 1 1 d . . . . .
H1 H 0.595229 0.060667 0.339048 0.036 Uiso 1 1 calc R U . . .
C2 C 0.6503(6) -0.0441(11) 0.4413(5) 0.033(2) Uani 1 1 d . . . . .
H2 H 0.604318 -0.019470 0.475623 0.039 Uiso 1 1 calc R U . . .
C3 C 0.7221(6) -0.1305(12) 0.4715(5) 0.036(2) Uani 1 1 d . . . . .
H3 H 0.725700 -0.167191 0.526782 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7888(6) -0.1632(11) 0.4212(5) 0.032(2) Uani 1 1 d . . . . .
H4 H 0.838207 -0.224156 0.441113 0.038 Uiso 1 1 calc R U . . .
C5 C 0.7827(5) -0.1064(10) 0.3417(5) 0.0220(18) Uani 1 1 d . . . . .
C6 C 0.8470(5) -0.1392(10) 0.2798(4) 0.0237(18) Uani 1 1 d . . . . .
C7 C 0.9226(5) -0.2294(10) 0.2958(5) 0.0251(18) Uani 1 1 d . . . . .
H7 H 0.936992 -0.268078 0.349596 0.030 Uiso 1 1 calc R U . . .
C8 C 0.9770(5) -0.2632(10) 0.2338(5) 0.0253(18) Uani 1 1 d . . . . .
H8 H 1.029002 -0.324775 0.244362 0.030 Uiso 1 1 calc R U . . .
C9 C 0.9548(5) -0.2060(10) 0.1560(5) 0.0254(19) Uani 1 1 d . . . . .
C10 C 0.8795(6) -0.1155(10) 0.1400(5) 0.0236(18) Uani 1 1 d . . . . .
H10 H 0.865831 -0.078401 0.085828 0.028 Uiso 1 1 calc R U . . .
C11 C 0.8235(5) -0.0774(9) 0.2008(4) 0.0169(16) Uani 1 1 d . . . . .
C12 C 0.7242(5) 0.3303(11) 0.1935(4) 0.0257(19) Uani 1 1 d . . . . .
C13 C 0.6319(5) 0.3012(10) 0.1889(4) 0.0199(17) Uani 1 1 d . . . . .
C14 C 0.6113(5) 0.2101(11) 0.1171(5) 0.0254(19) Uani 1 1 d . . . . .
C15 C 0.6909(6) 0.1852(10) 0.0739(4) 0.0261(19) Uani 1 1 d . . . . .
C16 C 0.7587(6) 0.2702(10) 0.1185(5) 0.030(2) Uani 1 1 d . . . . .
C17 C 0.7713(6) 0.4371(11) 0.2568(5) 0.035(2) Uani 1 1 d . . . . .
H17A H 0.831961 0.403452 0.260079 0.052 Uiso 1 1 calc R U . . .
H17B H 0.746202 0.418651 0.309819 0.052 Uiso 1 1 calc R U . . .
H17C H 0.766537 0.558998 0.241925 0.052 Uiso 1 1 calc R U . . .
C18 C 0.5714(6) 0.3689(11) 0.2496(5) 0.033(2) Uani 1 1 d . . . . .
H18A H 0.561194 0.491707 0.239637 0.050 Uiso 1 1 calc R U . . .
H18B H 0.596674 0.352944 0.304851 0.050 Uiso 1 1 calc R U . . .
H18C H 0.516892 0.306268 0.244147 0.050 Uiso 1 1 calc R U . . .
C19 C 0.5243(6) 0.1478(12) 0.0879(6) 0.040(2) Uani 1 1 d . . . . .
H19A H 0.481611 0.181814 0.126974 0.060 Uiso 1 1 calc R U . . .
H19B H 0.525095 0.022010 0.083089 0.060 Uiso 1 1 calc R U . . .
H19C H 0.509264 0.198655 0.034538 0.060 Uiso 1 1 calc R U . . .
C20 C 0.6950(8) 0.1008(12) -0.0088(5) 0.043(3) Uani 1 1 d . . . . .
H20A H 0.674252 0.181499 -0.051113 0.065 Uiso 1 1 calc R U . . .
H20B H 0.658932 -0.002578 -0.010424 0.065 Uiso 1 1 calc R U . . .
H20C H 0.754548 0.068764 -0.018438 0.065 Uiso 1 1 calc R U . . .
C21 C 0.8470(6) 0.2989(12) 0.0936(5) 0.038(2) Uani 1 1 d . . . . .
H21A H 0.860775 0.215121 0.051457 0.057 Uiso 1 1 calc R U . . .
H21B H 0.886966 0.284892 0.140869 0.057 Uiso 1 1 calc R U . . .
H21C H 0.851997 0.415700 0.071773 0.057 Uiso 1 1 calc R U . . .
C22 C 1.0142(6) -0.2346(12) 0.0887(5) 0.034(2) Uani 1 1 d D U . . .


_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 C11 2.040(8) . ?
Ir1 N1 2.094(6) . ?
Ir1 C12 2.145(9) . ?
Ir1 C15 2.158(7) . ?
Ir1 C16 2.183(8) . ?
Ir1 C14 2.256(8) . ?
Ir1 C13 2.269(7) . ?
Ir1 Cl1 2.410(2) . ?
F1A C22 1.34(2) . ?
F1B C22 1.26(2) . ?
F2A C22 1.296(19) . ?
F2B C22 1.369(9) . ?
F3A C22 1.332(13) . ?
F3B C22 1.331(18) . ?
N1 C5 1.354(10) . ?
N1 C1 1.355(10) . ?
C1 C2 1.377(12) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.378(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.479(11) . ?
C6 C7 1.387(11) . ?
C6 C11 1.417(10) . ?
C7 C8 1.378(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.381(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(11) . ?
C9 C22 1.489(12) . ?
C10 C11 1.385(11) . ?
C10 H10 0.9500 . ?
C12 C16 1.442(11) . ?
C12 C13 1.455(11) . ?
C12 C17 1.496(11) . ?
C13 C14 1.399(10) . ?
C13 C18 1.496(11) . ?
C14 C15 1.469(12) . ?
C14 C19 1.498(12) . ?
C15 C16 1.423(12) . ?
C15 C20 1.510(11) . ?
C16 C21 1.468(12) . ?
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 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C11 Ir1 N1 78.1(3) . . ?
C11 Ir1 C12 114.7(3) . . ?
N1 Ir1 C12 104.8(3) . . ?
C11 Ir1 C15 114.0(3) . . ?
N1 Ir1 C15 166.2(3) . . ?
C12 Ir1 C15 64.7(3) . . ?
C11 Ir1 C16 97.0(3) . . ?
N1 Ir1 C16 137.6(3) . . ?
C12 Ir1 C16 38.9(3) . . ?
C15 Ir1 C16 38.3(3) . . ?
C11 Ir1 C14 152.5(3) . . ?
N1 Ir1 C14 129.4(3) . . ?
C12 Ir1 C14 63.3(3) . . ?
C15 Ir1 C14 38.8(3) . . ?
C16 Ir1 C14 63.7(3) . . ?
C11 Ir1 C13 152.9(3) . . ?
N1 Ir1 C13 103.1(2) . . ?
C12 Ir1 C13 38.3(3) . . ?
C15 Ir1 C13 63.1(3) . . ?
C16 Ir1 C13 63.5(3) . . ?
C14 Ir1 C13 36.0(3) . . ?
C11 Ir1 Cl1 88.2(2) . . ?
N1 Ir1 Cl1 85.96(17) . . ?
C12 Ir1 Cl1 156.0(2) . . ?
C15 Ir1 Cl1 100.5(2) . . ?
C16 Ir1 Cl1 136.3(2) . . ?
C14 Ir1 Cl1 93.2(2) . . ?
C13 Ir1 Cl1 118.9(2) . . ?
C5 N1 C1 119.3(7) . . ?
C5 N1 Ir1 117.5(5) . . ?
C1 N1 Ir1 123.1(6) . . ?
N1 C1 C2 121.1(8) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C1 C2 C3 119.3(8) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 119.7(8) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.1(9) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.4(8) . . ?
N1 C5 C6 113.4(7) . . ?
C4 C5 C6 125.1(8) . . ?
C7 C6 C11 121.8(8) . . ?
C7 C6 C5 123.6(7) . . ?
C11 C6 C5 114.5(7) . . ?
C8 C7 C6 120.1(7) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 118.9(8) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C8 C9 C10 121.0(8) . . ?
C8 C9 C22 120.0(8) . . ?
C10 C9 C22 119.0(7) . . ?
C9 C10 C11 121.8(7) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C6 116.2(7) . . ?
C10 C11 Ir1 127.6(5) . . ?
C6 C11 Ir1 116.2(6) . . ?
C16 C12 C13 108.1(7) . . ?
C16 C12 C17 125.6(8) . . ?
C13 C12 C17 125.2(7) . . ?
C16 C12 Ir1 72.0(5) . . ?
C13 C12 Ir1 75.4(5) . . ?
C17 C12 Ir1 128.1(5) . . ?
C14 C13 C12 108.2(7) . . ?
C14 C13 C18 127.6(7) . . ?
C12 C13 C18 124.1(7) . . ?
C14 C13 Ir1 71.5(4) . . ?
C12 C13 Ir1 66.2(4) . . ?
C18 C13 Ir1 130.5(5) . . ?
C13 C14 C15 107.8(7) . . ?
C13 C14 C19 127.2(8) . . ?
C15 C14 C19 125.0(8) . . ?
C13 C14 Ir1 72.5(4) . . ?
C15 C14 Ir1 67.0(4) . . ?
C19 C14 Ir1 126.0(6) . . ?
C16 C15 C14 108.3(7) . . ?
C16 C15 C20 127.2(8) . . ?
C14 C15 C20 124.2(8) . . ?
C16 C15 Ir1 71.9(4) . . ?
C14 C15 Ir1 74.2(4) . . ?
C20 C15 Ir1 125.2(6) . . ?
C15 C16 C12 107.1(8) . . ?
C15 C16 C21 127.6(8) . . ?
C12 C16 C21 125.3(8) . . ?
C15 C16 Ir1 69.9(4) . . ?
C12 C16 Ir1 69.1(4) . . ?
C21 C16 Ir1 127.7(6) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
F1B C22 F3B 72.7(13) . . ?
F2A C22 F3A 73.3(11) . . ?
F2A C22 F1A 104.6(15) . . ?
F3A C22 F1A 126.3(12) . . ?
F1B C22 F2B 105.9(14) . . ?
F3B C22 F2B 135.8(12) . . ?
F1B C22 C9 115.6(14) . . ?
F2A C22 C9 114.8(11) . . ?
F3B C22 C9 109.8(10) . . ?
F3A C22 C9 114.4(8) . . ?
F1A C22 C9 114.4(12) . . ?
F2B C22 C9 110.0(10) . . ?

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
C5 N1 C1 C2 3.2(12) . . . . ?
Ir1 N1 C1 C2 -178.9(6) . . . . ?
N1 C1 C2 C3 -3.0(13) . . . . ?
C1 C2 C3 C4 0.9(13) . . . . ?
C2 C3 C4 C5 1.0(13) . . . . ?
C1 N1 C5 C4 -1.3(11) . . . . ?
Ir1 N1 C5 C4 -179.3(6) . . . . ?
C1 N1 C5 C6 175.3(7) . . . . ?
Ir1 N1 C5 C6 -2.7(8) . . . . ?
C3 C4 C5 N1 -0.8(12) . . . . ?
C3 C4 C5 C6 -176.9(8) . . . . ?
N1 C5 C6 C7 -177.7(7) . . . . ?
C4 C5 C6 C7 -1.3(13) . . . . ?
N1 C5 C6 C11 -0.5(10) . . . . ?
C4 C5 C6 C11 175.9(7) . . . . ?
C11 C6 C7 C8 -0.8(12) . . . . ?
C5 C6 C7 C8 176.3(8) . . . . ?
C6 C7 C8 C9 -0.1(12) . . . . ?
C7 C8 C9 C10 0.3(12) . . . . ?
C7 C8 C9 C22 177.5(8) . . . . ?
C8 C9 C10 C11 0.4(12) . . . . ?
C22 C9 C10 C11 -176.9(8) . . . . ?
C9 C10 C11 C6 -1.2(11) . . . . ?
C9 C10 C11 Ir1 179.4(6) . . . . ?
C7 C6 C11 C10 1.4(12) . . . . ?
C5 C6 C11 C10 -175.9(7) . . . . ?
C7 C6 C11 Ir1 -179.2(6) . . . . ?
C5 C6 C11 Ir1 3.5(9) . . . . ?
C16 C12 C13 C14 5.8(9) . . . . ?
C17 C12 C13 C14 174.1(7) . . . . ?
Ir1 C12 C13 C14 -59.3(6) . . . . ?
C16 C12 C13 C18 -171.0(7) . . . . ?
C17 C12 C13 C18 -2.7(12) . . . . ?
Ir1 C12 C13 C18 123.9(7) . . . . ?
C16 C12 C13 Ir1 65.1(6) . . . . ?
C17 C12 C13 Ir1 -126.7(8) . . . . ?
C12 C13 C14 C15 -1.8(9) . . . . ?
C18 C13 C14 C15 174.8(8) . . . . ?
Ir1 C13 C14 C15 -57.9(5) . . . . ?
C12 C13 C14 C19 178.4(8) . . . . ?
C18 C13 C14 C19 -5.0(14) . . . . ?
Ir1 C13 C14 C19 122.3(9) . . . . ?
C12 C13 C14 Ir1 56.1(5) . . . . ?
C18 C13 C14 Ir1 -127.3(8) . . . . ?
C13 C14 C15 C16 -2.9(9) . . . . ?
C19 C14 C15 C16 176.9(8) . . . . ?
Ir1 C14 C15 C16 -64.3(5) . . . . ?
C13 C14 C15 C20 -176.5(7) . . . . ?
C19 C14 C15 C20 3.4(13) . . . . ?
Ir1 C14 C15 C20 122.2(8) . . . . ?
C13 C14 C15 Ir1 61.4(5) . . . . ?
C19 C14 C15 Ir1 -118.8(8) . . . . ?
C14 C15 C16 C12 6.4(9) . . . . ?
C20 C15 C16 C12 179.7(7) . . . . ?
Ir1 C15 C16 C12 -59.4(5) . . . . ?
C14 C15 C16 C21 -171.6(8) . . . . ?
C20 C15 C16 C21 1.8(13) . . . . ?
Ir1 C15 C16 C21 122.6(8) . . . . ?
C14 C15 C16 Ir1 65.8(5) . . . . ?
C20 C15 C16 Ir1 -120.9(8) . . . . ?
C13 C12 C16 C15 -7.5(9) . . . . ?
C17 C12 C16 C15 -175.7(7) . . . . ?
Ir1 C12 C16 C15 59.9(5) . . . . ?
C13 C12 C16 C21 170.5(7) . . . . ?
C17 C12 C16 C21 2.3(13) . . . . ?
Ir1 C12 C16 C21 -122.1(8) . . . . ?
C13 C12 C16 Ir1 -67.4(6) . . . . ?
C17 C12 C16 Ir1 124.4(8) . . . . ?
C8 C9 C22 F1B 134.2(13) . . . . ?
C10 C9 C22 F1B -48.5(15) . . . . ?
C8 C9 C22 F2A -73.0(14) . . . . ?
C10 C9 C22 F2A 104.2(13) . . . . ?
C8 C9 C22 F3B 54.5(15) . . . . ?
C10 C9 C22 F3B -128.2(13) . . . . ?
C8 C9 C22 F3A 9.0(13) . . . . ?
C10 C9 C22 F3A -173.7(10) . . . . ?
C8 C9 C22 F1A 166.0(12) . . . . ?
C10 C9 C22 F1A -16.8(15) . . . . ?
C8 C9 C22 F2B -105.9(11) . . . . ?
C10 C9 C22 F2B 71.4(12) . . . . ?

_refine_diff_density_max         1.834
_refine_diff_density_min         -1.009
_refine_diff_density_rms         0.225

####################################################################### 
# 
# 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_18040
_database_code_depnum_ccdc_archive 'CCDC 1959429'
_audit_update_record             
;
2020-02-04 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 Cl F N Rh'
_chemical_formula_sum            'C21 H22 Cl F N Rh'
_chemical_formula_weight         445.75

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   7.3923(14)
_cell_length_b                   14.787(3)
_cell_length_c                   16.815(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.990(3)
_cell_angle_gamma                90
_cell_volume                     1824.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    913
_cell_measurement_theta_min      2.803
_cell_measurement_theta_max      27.035

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.095
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   
;
absoprtion correction based on 9289 reflections(SADABS);rint 0.0713 before
correction and 0.0356 after.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13907
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3586
_reflns_number_gt                3184
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²+0.2995P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3586
_refine_ls_number_parameters     353
_refine_ls_number_restraints     613
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0747
_refine_ls_wR_factor_gt          0.0724
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.002
_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_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
Rh1 Rh 0.33996(3) 0.25843(2) 0.31136(2) 0.01925(9) Uani 1 1 d . U . . .
Cl1 Cl 0.05864(10) 0.32358(5) 0.34092(5) 0.03168(18) Uani 1 1 d . U . . .
F1A F 0.3670(6) 0.1579(3) 0.4909(2) 0.0466(10) Uani 0.5 1 d . U P A .
F1B F 0.2498(5) 0.3251(3) 0.1197(2) 0.0458(10) Uani 0.5 1 d . U P A .
N1A N 0.261(4) 0.1306(15) 0.3535(19) 0.022(3) Uani 0.5 1 d . U P A .
C1A C 0.244(5) 0.1416(19) 0.352(2) 0.017(2) Uani 0.5 1 d . U P A .
N1B N 0.197(4) 0.1992(19) 0.2060(18) 0.024(3) Uani 0.5 1 d . U P A .
C1B C 0.217(4) 0.204(2) 0.210(2) 0.021(2) Uani 0.5 1 d . U P A .
C2 C 0.2702(4) 0.1079(2) 0.43041(18) 0.0301(7) Uani 1 1 d D U . . .
H2 H 0.335040 0.148038 0.470518 0.036 Uiso 0.5 1 d DR U P A .
C3 C 0.2063(5) 0.0260(2) 0.4539(2) 0.0393(8) Uani 1 1 d . U . . .
H3 H 0.223095 0.009093 0.507549 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1168(5) -0.0309(2) 0.3967(2) 0.0393(8) Uani 1 1 d . U . . .
H4 H 0.072517 -0.086459 0.411558 0.047 Uiso 1 1 calc R U . . .
C5 C 0.0941(4) -0.0044(2) 0.3178(2) 0.0324(7) Uani 1 1 d . U . . .
H5 H 0.033693 -0.041887 0.278840 0.039 Uiso 1 1 calc R U . . .
C6 C 0.1625(4) 0.07938(19) 0.29630(18) 0.0246(6) Uani 1 1 d . U . . .
C7 C 0.1424(4) 0.11446(19) 0.21440(18) 0.0244(6) Uani 1 1 d . U . . .
C8 C 0.0647(4) 0.0666(2) 0.14714(19) 0.0323(7) Uani 1 1 d . U . . .
H8 H 0.023877 0.007659 0.152386 0.039 Uiso 1 1 calc R U . . .
C9 C 0.0492(4) 0.1074(2) 0.07300(19) 0.0359(8) Uani 1 1 d . U . . .
H9 H -0.000321 0.075627 0.027807 0.043 Uiso 1 1 calc R U . . .
C10 C 0.1068(4) 0.1952(2) 0.06571(19) 0.0346(7) Uani 1 1 d . U . . .
H10 H 0.094689 0.223882 0.016140 0.042 Uiso 1 1 calc R U . . .
C11 C 0.1828(5) 0.2393(2) 0.1338(2) 0.0319(7) Uani 1 1 d D U . . .
H11 H 0.223710 0.300383 0.130748 0.038 Uiso 0.5 1 d DR U P A .
C12A C 0.632(4) 0.2388(19) 0.3396(11) 0.023(2) Uani 0.5 1 d . U P A 1
C12B C 0.624(4) 0.2486(18) 0.3530(11) 0.023(2) Uani 0.5 1 d . U P A 2
C13A C 0.576(3) 0.2937(9) 0.4027(11) 0.027(2) Uani 0.5 1 d . U P A 1
C13B C 0.553(3) 0.3193(9) 0.3956(10) 0.024(2) Uani 0.5 1 d . U P A 2
C14A C 0.5020(19) 0.3732(8) 0.3696(6) 0.030(2) Uani 0.5 1 d . U P A 1
C14B C 0.4922(17) 0.3882(7) 0.3379(7) 0.025(2) Uani 0.5 1 d . U P A 2
C15A C 0.5080(19) 0.3723(8) 0.2852(8) 0.025(2) Uani 0.5 1 d . U P A 1
C15B C 0.520(2) 0.3583(10) 0.2608(7) 0.026(2) Uani 0.5 1 d . U P A 2
C16A C 0.594(4) 0.2896(12) 0.2678(14) 0.023(2) Uani 0.5 1 d . U P A 1
C16B C 0.603(4) 0.2696(12) 0.2677(16) 0.027(3) Uani 0.5 1 d . U P A 2
C17A C 0.7285(17) 0.1501(7) 0.3518(6) 0.038(2) Uani 0.5 1 d . U P A 1
H17A H 0.740731 0.123359 0.300679 0.057 Uiso 0.5 1 calc R U P A 1
H17B H 0.659548 0.110377 0.381814 0.057 Uiso 0.5 1 calc R U P A 1
H17C H 0.847178 0.159478 0.380708 0.057 Uiso 0.5 1 calc R U P A 1
C17B C 0.7221(16) 0.1646(7) 0.3878(6) 0.037(2) Uani 0.5 1 d . U P A 2
H17D H 0.684086 0.151490 0.439158 0.055 Uiso 0.5 1 calc R U P A 2
H17E H 0.851267 0.174835 0.393800 0.055 Uiso 0.5 1 calc R U P A 2
H17F H 0.692847 0.114359 0.352385 0.055 Uiso 0.5 1 calc R U P A 2
C18A C 0.6047(12) 0.2724(7) 0.4909(4) 0.048(2) Uani 0.5 1 d . U P A 1
H18A H 0.712108 0.302872 0.515229 0.072 Uiso 0.5 1 calc R U P A 1
H18B H 0.619327 0.208358 0.498237 0.072 Uiso 0.5 1 calc R U P A 1
H18C H 0.501122 0.292511 0.515470 0.072 Uiso 0.5 1 calc R U P A 1
C18B C 0.5650(11) 0.3300(6) 0.4843(4) 0.0385(17) Uani 0.5 1 d . U P A 2
H18D H 0.581526 0.271724 0.509339 0.058 Uiso 0.5 1 calc R U P A 2
H18E H 0.454806 0.356918 0.497930 0.058 Uiso 0.5 1 calc R U P A 2
H18F H 0.666718 0.368092 0.502577 0.058 Uiso 0.5 1 calc R U P A 2
C19A C 0.4250(11) 0.4514(5) 0.4119(6) 0.051(2) Uani 0.5 1 d . U P A 1
H19A H 0.400047 0.432371 0.464106 0.077 Uiso 0.5 1 calc R U P A 1
H19B H 0.314190 0.471583 0.381415 0.077 Uiso 0.5 1 calc R U P A 1
H19C H 0.511668 0.499995 0.417322 0.077 Uiso 0.5 1 calc R U P A 1
C19B C 0.4151(11) 0.4776(5) 0.3574(5) 0.0421(18) Uani 0.5 1 d . U P A 2
H19D H 0.512526 0.519979 0.370554 0.063 Uiso 0.5 1 calc R U P A 2
H19E H 0.347281 0.471057 0.402233 0.063 Uiso 0.5 1 calc R U P A 2
H19F H 0.335896 0.499303 0.311900 0.063 Uiso 0.5 1 calc R U P A 2
C20A C 0.4545(10) 0.4497(5) 0.2296(5) 0.0432(18) Uani 0.5 1 d . U P A 1
H20A H 0.488816 0.436484 0.177579 0.065 Uiso 0.5 1 calc R U P A 1
H20B H 0.515339 0.503692 0.250166 0.065 Uiso 0.5 1 calc R U P A 1
H20C H 0.324993 0.458460 0.225456 0.065 Uiso 0.5 1 calc R U P A 1
C20B C 0.4760(11) 0.4134(6) 0.1851(5) 0.047(2) Uani 0.5 1 d . U P A 2
H20D H 0.347977 0.426703 0.177341 0.071 Uiso 0.5 1 calc R U P A 2
H20E H 0.508010 0.379525 0.140140 0.071 Uiso 0.5 1 calc R U P A 2
H20F H 0.543992 0.468828 0.189795 0.071 Uiso 0.5 1 calc R U P A 2
C21A C 0.6620(14) 0.2618(5) 0.1898(5) 0.0340(19) Uani 0.5 1 d . U P A 1
H21A H 0.629754 0.199837 0.178279 0.051 Uiso 0.5 1 calc R U P A 1
H21B H 0.792097 0.268231 0.194464 0.051 Uiso 0.5 1 calc R U P A 1
H21C H 0.606905 0.299602 0.147131 0.051 Uiso 0.5 1 calc R U P A 1
C21B C 0.6662(14) 0.2156(6) 0.2023(6) 0.041(2) Uani 0.5 1 d . U P A 2
H21D H 0.787593 0.233634 0.194623 0.062 Uiso 0.5 1 calc R U P A 2
H21E H 0.586043 0.225551 0.153729 0.062 Uiso 0.5 1 calc R U P A 2
H21F H 0.665588 0.152626 0.216076 0.062 Uiso 0.5 1 calc R U P A 2


_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
Rh1 C1B 2.00(3) . ?
Rh1 C1A 2.02(3) . ?
Rh1 N1A 2.13(2) . ?
Rh1 N1B 2.14(2) . ?
Rh1 C12B 2.14(3) . ?
Rh1 C16A 2.15(3) . ?
Rh1 C16B 2.17(3) . ?
Rh1 C15A 2.170(14) . ?
Rh1 C12A 2.17(3) . ?
Rh1 C13B 2.179(19) . ?
Rh1 C15B 2.227(15) . ?
Rh1 C14A 2.233(13) . ?
F1A C2 1.384(5) . ?
F1A H2 0.4178 . ?
F1B C11 1.392(4) . ?
F1B H11 0.4625 . ?
N1A C2 1.33(3) . ?
N1A C6 1.36(3) . ?
C1A C6 1.40(4) . ?
C1A C2 1.40(3) . ?
N1B C7 1.33(3) . ?
N1B C11 1.34(3) . ?
C1B C11 1.38(4) . ?
C1B C7 1.44(3) . ?
C2 C3 1.375(4) . ?
C2 H2 0.9785 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.402(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.462(4) . ?
C7 C8 1.397(4) . ?
C8 C9 1.377(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.376(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.377(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9557 . ?
C12A C16A 1.42(3) . ?
C12A C13A 1.438(19) . ?
C12A C17A 1.50(3) . ?
C12B C13B 1.405(19) . ?
C12B C16B 1.46(3) . ?
C12B C17B 1.52(2) . ?
C13A C14A 1.383(13) . ?
C13A C18A 1.505(18) . ?
C13B C14B 1.441(13) . ?
C13B C18B 1.491(17) . ?
C14A C15A 1.426(13) . ?
C14A C19A 1.505(14) . ?
C14B C15B 1.409(12) . ?
C14B C19B 1.492(13) . ?
C15A C16A 1.426(17) . ?
C15A C20A 1.500(15) . ?
C15B C16B 1.448(18) . ?
C15B C20B 1.512(16) . ?
C16A C21A 1.52(2) . ?
C16B C21B 1.48(2) . ?
C17A H17A 0.9600 . ?
C17A H17B 0.9600 . ?
C17A H17C 0.9600 . ?
C17B H17D 0.9600 . ?
C17B H17E 0.9600 . ?
C17B H17F 0.9600 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?
C20A H20A 0.9600 . ?
C20A H20B 0.9600 . ?
C20A H20C 0.9600 . ?
C20B H20D 0.9600 . ?
C20B H20E 0.9600 . ?
C20B H20F 0.9600 . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?

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
C1B Rh1 C1A 78.6(15) . . ?
C1B Rh1 N1A 79.2(13) . . ?
C1A Rh1 N1A 4.9(17) . . ?
C1B Rh1 N1B 3(2) . . ?
C1A Rh1 N1B 76.7(13) . . ?
N1A Rh1 N1B 77.5(12) . . ?
C1B Rh1 C12B 125.4(12) . . ?
C1A Rh1 C12B 101.8(13) . . ?
N1A Rh1 C12B 97.5(12) . . ?
N1B Rh1 C12B 127.7(10) . . ?
C1B Rh1 C16A 97.0(13) . . ?
C1A Rh1 C16A 131.2(10) . . ?
N1A Rh1 C16A 126.3(9) . . ?
N1B Rh1 C16A 99.9(12) . . ?
C1B Rh1 C16B 94.4(15) . . ?
C1A Rh1 C16B 123.2(10) . . ?
N1A Rh1 C16B 118.4(9) . . ?
N1B Rh1 C16B 97.2(11) . . ?
C12B Rh1 C16B 39.6(9) . . ?
C1B Rh1 C15A 110.6(11) . . ?
C1A Rh1 C15A 165.3(12) . . ?
N1A Rh1 C15A 161.0(9) . . ?
N1B Rh1 C15A 112.8(9) . . ?
C16A Rh1 C15A 38.5(5) . . ?
C1B Rh1 C12A 118.0(13) . . ?
C1A Rh1 C12A 101.2(13) . . ?
N1A Rh1 C12A 96.6(12) . . ?
N1B Rh1 C12A 120.3(10) . . ?
C16A Rh1 C12A 38.4(9) . . ?
C15A Rh1 C12A 64.5(9) . . ?
C1B Rh1 C13B 159.6(13) . . ?
C1A Rh1 C13B 112.9(12) . . ?
N1A Rh1 C13B 110.9(10) . . ?
N1B Rh1 C13B 162.5(10) . . ?
C12B Rh1 C13B 38.0(6) . . ?
C16B Rh1 C13B 65.3(9) . . ?
C1B Rh1 C15B 99.9(11) . . ?
C1A Rh1 C15B 161.7(10) . . ?
N1A Rh1 C15B 156.8(9) . . ?
N1B Rh1 C15B 102.4(9) . . ?
C12B Rh1 C15B 63.9(9) . . ?
C16B Rh1 C15B 38.4(5) . . ?
C13B Rh1 C15B 63.7(5) . . ?
C1B Rh1 C14A 147.5(10) . . ?
C1A Rh1 C14A 133.9(11) . . ?
N1A Rh1 C14A 133.2(10) . . ?
N1B Rh1 C14A 149.3(8) . . ?
C16A Rh1 C14A 62.7(7) . . ?
C15A Rh1 C14A 37.8(4) . . ?
C12A Rh1 C14A 62.6(7) . . ?
C2 N1A C6 120.5(19) . . ?
C2 N1A Rh1 124(2) . . ?
C6 N1A Rh1 113.8(16) . . ?
C6 C1A C2 113.4(19) . . ?
C6 C1A Rh1 118(2) . . ?
C2 C1A Rh1 127(2) . . ?
C7 N1B C11 121.4(16) . . ?
C7 N1B Rh1 115.1(17) . . ?
C11 N1B Rh1 122.9(14) . . ?
C11 C1B C7 111.5(16) . . ?
C11 C1B Rh1 130.8(18) . . ?
C7 C1B Rh1 118(2) . . ?
N1A C2 C3 121.5(13) . . ?
N1A C2 F1A 122.8(13) . . ?
C3 C2 F1A 115.1(3) . . ?
C3 C2 C1A 124.7(15) . . ?
F1A C2 C1A 120.2(15) . . ?
N1A C2 H2 118.7 . . ?
C3 C2 H2 119.5 . . ?
C1A C2 H2 115.7 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
N1A C6 C5 119.1(11) . . ?
C1A C6 C5 123.2(12) . . ?
N1A C6 C7 116.9(11) . . ?
C1A C6 C7 112.6(12) . . ?
C5 C6 C7 123.9(3) . . ?
N1B C7 C8 119.4(12) . . ?
C8 C7 C1B 123.2(14) . . ?
N1B C7 C6 115.9(12) . . ?
C8 C7 C6 124.6(3) . . ?
C1B C7 C6 112.2(14) . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 118.2(3) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
N1B C11 C10 121.3(9) . . ?
C10 C11 C1B 127.2(11) . . ?
N1B C11 F1B 124.5(9) . . ?
C10 C11 F1B 114.1(3) . . ?
C1B C11 F1B 118.2(10) . . ?
N1B C11 H11 118.4 . . ?
C10 C11 H11 120.2 . . ?
C1B C11 H11 112.5 . . ?
C16A C12A C13A 106.5(18) . . ?
C16A C12A C17A 128.4(14) . . ?
C13A C12A C17A 124.8(17) . . ?
C16A C12A Rh1 70.0(17) . . ?
C13A C12A Rh1 73.5(13) . . ?
C17A C12A Rh1 126(2) . . ?
C13B C12B C16B 110.1(18) . . ?
C13B C12B C17B 127.1(15) . . ?
C16B C12B C17B 122.7(14) . . ?
C13B C12B Rh1 72.7(14) . . ?
C16B C12B Rh1 71.5(16) . . ?
C17B C12B Rh1 126(2) . . ?
C14A C13A C12A 108.5(17) . . ?
C14A C13A C18A 125.2(13) . . ?
C12A C13A C18A 126.1(13) . . ?
C14A C13A Rh1 71.8(9) . . ?
C12A C13A Rh1 68.5(15) . . ?
C18A C13A Rh1 129.3(12) . . ?
C12B C13B C14B 106.7(15) . . ?
C12B C13B C18B 127.4(13) . . ?
C14B C13B C18B 125.1(10) . . ?
C12B C13B Rh1 69.4(15) . . ?
C14B C13B Rh1 73.4(8) . . ?
C18B C13B Rh1 130.2(13) . . ?
C13A C14A C15A 109.6(12) . . ?
C13A C14A C19A 127.9(12) . . ?
C15A C14A C19A 122.5(10) . . ?
C13A C14A Rh1 72.2(10) . . ?
C15A C14A Rh1 68.7(7) . . ?
C19A C14A Rh1 125.3(8) . . ?
C15B C14B C13B 109.3(11) . . ?
C15B C14B C19B 125.7(11) . . ?
C13B C14B C19B 125.1(11) . . ?
C15B C14B Rh1 71.0(8) . . ?
C13B C14B Rh1 68.6(9) . . ?
C19B C14B Rh1 127.3(8) . . ?
C14A C15A C16A 106.3(13) . . ?
C14A C15A C20A 125.1(10) . . ?
C16A C15A C20A 128.1(13) . . ?
C14A C15A Rh1 73.6(8) . . ?
C16A C15A Rh1 70.0(12) . . ?
C20A C15A Rh1 127.2(9) . . ?
C14B C15B C16B 108.6(15) . . ?
C14B C15B C20B 124.4(12) . . ?
C16B C15B C20B 127.0(12) . . ?
C14B C15B Rh1 72.2(7) . . ?
C16B C15B Rh1 68.7(13) . . ?
C20B C15B Rh1 126.9(9) . . ?
C15A C16A C12A 109.0(17) . . ?
C15A C16A C21A 127.8(15) . . ?
C12A C16A C21A 122.7(13) . . ?
C15A C16A Rh1 71.5(11) . . ?
C12A C16A Rh1 71.7(17) . . ?
C21A C16A Rh1 129.0(18) . . ?
C12B C16B C15B 105.3(17) . . ?
C12B C16B C21B 127.8(15) . . ?
C15B C16B C21B 126.7(18) . . ?
C12B C16B Rh1 69.0(16) . . ?
C15B C16B Rh1 72.9(11) . . ?
C21B C16B Rh1 125.9(18) . . ?
C12A C17A H17A 109.5 . . ?
C12A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C12A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C12B C17B H17D 109.5 . . ?
C12B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C12B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C13A C18A H18A 109.5 . . ?
C13A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C13A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C13B C18B H18D 109.5 . . ?
C13B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C13B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C14A C19A H19A 109.5 . . ?
C14A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C14A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C14B C19B H19D 109.5 . . ?
C14B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C14B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C15A C20A H20A 109.5 . . ?
C15A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C15A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C15B C20B H20D 109.5 . . ?
C15B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C15B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 109.5 . . ?
C16A C21A H21A 109.5 . . ?
C16A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
C16A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
C16B C21B H21D 109.5 . . ?
C16B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
C16B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?

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
C6 N1A C2 C3 10(3) . . . . ?
Rh1 N1A C2 C3 176.0(11) . . . . ?
C6 N1A C2 F1A -179.6(13) . . . . ?
Rh1 N1A C2 F1A -14(3) . . . . ?
C6 N1A C2 C1A -106(22) . . . . ?
Rh1 N1A C2 C1A 60(20) . . . . ?
C6 C1A C2 N1A 62(19) . . . . ?
Rh1 C1A C2 N1A -109(22) . . . . ?
C6 C1A C2 C3 -7(3) . . . . ?
Rh1 C1A C2 C3 -177.5(13) . . . . ?
C6 C1A C2 F1A 172.9(14) . . . . ?
Rh1 C1A C2 F1A 2(3) . . . . ?
N1A C2 C3 C4 -5.4(15) . . . . ?
F1A C2 C3 C4 -176.4(3) . . . . ?
C1A C2 C3 C4 3.5(17) . . . . ?
C2 C3 C4 C5 0.2(5) . . . . ?
C3 C4 C5 C6 0.3(5) . . . . ?
C2 N1A C6 C1A 112(18) . . . . ?
Rh1 N1A C6 C1A -55(16) . . . . ?
C2 N1A C6 C5 -9(3) . . . . ?
Rh1 N1A C6 C5 -176.7(7) . . . . ?
C2 N1A C6 C7 173.3(14) . . . . ?
Rh1 N1A C6 C7 6.1(19) . . . . ?
C2 C1A C6 N1A -56(15) . . . . ?
Rh1 C1A C6 N1A 115(18) . . . . ?
C2 C1A C6 C5 7(3) . . . . ?
Rh1 C1A C6 C5 178.8(10) . . . . ?
C2 C1A C6 C7 -177.7(16) . . . . ?
Rh1 C1A C6 C7 -6(2) . . . . ?
C4 C5 C6 N1A 4.2(14) . . . . ?
C4 C5 C6 C1A -4.5(17) . . . . ?
C4 C5 C6 C7 -178.8(3) . . . . ?
C11 N1B C7 C8 -2(3) . . . . ?
Rh1 N1B C7 C8 -173.3(9) . . . . ?
C11 N1B C7 C1B 133(37) . . . . ?
Rh1 N1B C7 C1B -39(33) . . . . ?
C11 N1B C7 C6 -179.1(18) . . . . ?
Rh1 N1B C7 C6 9(2) . . . . ?
C11 C1B C7 N1B -41(33) . . . . ?
Rh1 C1B C7 N1B 137(37) . . . . ?
C11 C1B C7 C8 7(4) . . . . ?
Rh1 C1B C7 C8 -175.3(12) . . . . ?
C11 C1B C7 C6 -174.7(19) . . . . ?
Rh1 C1B C7 C6 3(3) . . . . ?
N1A C6 C7 N1B -10(2) . . . . ?
C1A C6 C7 N1B -2(2) . . . . ?
C5 C6 C7 N1B 172.5(16) . . . . ?
N1A C6 C7 C8 172.3(13) . . . . ?
C1A C6 C7 C8 -179.6(15) . . . . ?
C5 C6 C7 C8 -4.8(4) . . . . ?
N1A C6 C7 C1B -6(2) . . . . ?
C1A C6 C7 C1B 2(2) . . . . ?
C5 C6 C7 C1B 176.9(17) . . . . ?
N1B C7 C8 C9 1.3(17) . . . . ?
C1B C7 C8 C9 -3.3(19) . . . . ?
C6 C7 C8 C9 178.5(3) . . . . ?
C7 C8 C9 C10 -1.2(5) . . . . ?
C8 C9 C10 C11 1.3(5) . . . . ?
C7 N1B C11 C10 2(3) . . . . ?
Rh1 N1B C11 C10 172.9(12) . . . . ?
C7 N1B C11 C1B -144(28) . . . . ?
Rh1 N1B C11 C1B 27(23) . . . . ?
C7 N1B C11 F1B -174.7(16) . . . . ?
Rh1 N1B C11 F1B -4(3) . . . . ?
C9 C10 C11 N1B -1.7(17) . . . . ?
C9 C10 C11 C1B 3(2) . . . . ?
C9 C10 C11 F1B 175.2(3) . . . . ?
C7 C1B C11 N1B 30(23) . . . . ?
Rh1 C1B C11 N1B -148(28) . . . . ?
C7 C1B C11 C10 -7(4) . . . . ?
Rh1 C1B C11 C10 175.6(18) . . . . ?
C7 C1B C11 F1B -178.7(16) . . . . ?
Rh1 C1B C11 F1B 4(4) . . . . ?
C16A C12A C13A C14A 2(3) . . . . ?
C17A C12A C13A C14A 176(2) . . . . ?
Rh1 C12A C13A C14A -60.9(15) . . . . ?
C16A C12A C13A C18A -174(2) . . . . ?
C17A C12A C13A C18A 1(4) . . . . ?
Rh1 C12A C13A C18A 123.7(19) . . . . ?
C16A C12A C13A Rh1 63(2) . . . . ?
C17A C12A C13A Rh1 -123(3) . . . . ?
C16B C12B C13B C14B -2(3) . . . . ?
C17B C12B C13B C14B 173(3) . . . . ?
Rh1 C12B C13B C14B -64.4(13) . . . . ?
C16B C12B C13B C18B -172(2) . . . . ?
C17B C12B C13B C18B 3(5) . . . . ?
Rh1 C12B C13B C18B 125(2) . . . . ?
C16B C12B C13B Rh1 62(2) . . . . ?
C17B C12B C13B Rh1 -122(3) . . . . ?
C12A C13A C14A C15A 0(2) . . . . ?
C18A C13A C14A C15A 175.6(15) . . . . ?
Rh1 C13A C14A C15A -58.7(10) . . . . ?
C12A C13A C14A C19A -179.9(18) . . . . ?
C18A C13A C14A C19A -4(3) . . . . ?
Rh1 C13A C14A C19A 121.3(13) . . . . ?
C12A C13A C14A Rh1 58.8(18) . . . . ?
C18A C13A C14A Rh1 -125.7(18) . . . . ?
C12B C13B C14B C15B 2(2) . . . . ?
C18B C13B C14B C15B 172.6(16) . . . . ?
Rh1 C13B C14B C15B -59.6(10) . . . . ?
C12B C13B C14B C19B -176.9(18) . . . . ?
C18B C13B C14B C19B -6(3) . . . . ?
Rh1 C13B C14B C19B 121.4(12) . . . . ?
C12B C13B C14B Rh1 61.7(18) . . . . ?
C18B C13B C14B Rh1 -127.8(18) . . . . ?
C13A C14A C15A C16A -2(2) . . . . ?
C19A C14A C15A C16A 178.1(16) . . . . ?
Rh1 C14A C15A C16A -62.8(15) . . . . ?
C13A C14A C15A C20A -174.9(14) . . . . ?
C19A C14A C15A C20A 5(2) . . . . ?
Rh1 C14A C15A C20A 124.3(13) . . . . ?
C13A C14A C15A Rh1 60.9(12) . . . . ?
C19A C14A C15A Rh1 -119.1(11) . . . . ?
C13B C14B C15B C16B -1(2) . . . . ?
C19B C14B C15B C16B 177.9(16) . . . . ?
Rh1 C14B C15B C16B -59.3(15) . . . . ?
C13B C14B C15B C20B -178.9(14) . . . . ?
C19B C14B C15B C20B 0(2) . . . . ?
Rh1 C14B C15B C20B 123.0(14) . . . . ?
C13B C14B C15B Rh1 58.1(11) . . . . ?
C19B C14B C15B Rh1 -122.9(12) . . . . ?
C14A C15A C16A C12A 3(3) . . . . ?
C20A C15A C16A C12A 176(2) . . . . ?
Rh1 C15A C16A C12A -62(2) . . . . ?
C14A C15A C16A C21A -169(2) . . . . ?
C20A C15A C16A C21A 3(4) . . . . ?
Rh1 C15A C16A C21A 125(3) . . . . ?
C14A C15A C16A Rh1 65.2(11) . . . . ?
C20A C15A C16A Rh1 -122.1(15) . . . . ?
C13A C12A C16A C15A -3(3) . . . . ?
C17A C12A C16A C15A -177(3) . . . . ?
Rh1 C12A C16A C15A 62.0(19) . . . . ?
C13A C12A C16A C21A 170(2) . . . . ?
C17A C12A C16A C21A -4(5) . . . . ?
Rh1 C12A C16A C21A -125(3) . . . . ?
C13A C12A C16A Rh1 -65(2) . . . . ?
C17A C12A C16A Rh1 121(3) . . . . ?
C13B C12B C16B C15B 2(3) . . . . ?
C17B C12B C16B C15B -174(2) . . . . ?
Rh1 C12B C16B C15B 64.4(18) . . . . ?
C13B C12B C16B C21B 177(2) . . . . ?
C17B C12B C16B C21B 1(5) . . . . ?
Rh1 C12B C16B C21B -120(3) . . . . ?
C13B C12B C16B Rh1 -63(2) . . . . ?
C17B C12B C16B Rh1 121(3) . . . . ?
C14B C15B C16B C12B 0(3) . . . . ?
C20B C15B C16B C12B 177(2) . . . . ?
Rh1 C15B C16B C12B -62(2) . . . . ?
C14B C15B C16B C21B -176(2) . . . . ?
C20B C15B C16B C21B 2(4) . . . . ?
Rh1 C15B C16B C21B 122(3) . . . . ?
C14B C15B C16B Rh1 61.5(12) . . . . ?
C20B C15B C16B Rh1 -120.9(15) . . . . ?

_refine_diff_density_max         0.717
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_17104
_database_code_depnum_ccdc_archive 'CCDC 1959428'
_audit_update_record             
;
2020-01-21 deposited with the CCDC.	2020-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 Cl F Ir N'
_chemical_formula_sum            'C21 H22 Cl F Ir N'
_chemical_formula_weight         535.04

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_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                   7.477(3)
_cell_length_b                   14.699(5)
_cell_length_c                   17.404(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.337(6)
_cell_angle_gamma                90
_cell_volume                     1875.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    963
_cell_measurement_theta_min      2.772
_cell_measurement_theta_max      27.234

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    7.274
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.365
_exptl_absorpt_correction_T_max  0.831
_exptl_absorpt_process_details   
;
absoprtion correction based on 8486 reflections(SADABS);Rint 0.1332 before
correction and 0.0483 after.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Apex 2000 CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14279
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.829
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3682
_reflns_number_gt                3100
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3682
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0807
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_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_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 0.61736(3) 0.08841(2) 0.79380(2) 0.02485(9) Uani 1 1 d . . . . .
Cl1 Cl 0.3452(2) 0.15283(10) 0.82474(11) 0.0366(4) Uani 1 1 d . . . . .
F1 F 0.2470(8) 0.0493(4) 0.4956(3) 0.0878(18) Uani 1 1 d . . . . .
N1 N 0.5417(6) -0.0318(3) 0.8443(3) 0.0268(11) Uani 1 1 d . . . . .
C1 C 0.5850(8) -0.0521(4) 0.9204(4) 0.0326(15) Uani 1 1 d . . . . .
H1 H 0.657157 -0.009940 0.954558 0.039 Uiso 1 1 calc R U . . .
C2 C 0.5306(9) -0.1312(4) 0.9523(4) 0.0367(16) Uani 1 1 d . . . . .
H2 H 0.563966 -0.143356 1.006869 0.044 Uiso 1 1 calc R U . . .
C3 C 0.4248(9) -0.1924(4) 0.9013(4) 0.0392(17) Uani 1 1 d . . . . .
H3 H 0.385361 -0.247528 0.921074 0.047 Uiso 1 1 calc R U . . .
C4 C 0.3776(8) -0.1734(4) 0.8229(4) 0.0317(14) Uani 1 1 d . . . . .
H4 H 0.305932 -0.215220 0.788250 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4359(8) -0.0916(4) 0.7942(4) 0.0297(14) Uani 1 1 d . . . . .
C6 C 0.3909(8) -0.0608(4) 0.7133(4) 0.0289(14) Uani 1 1 d . . . . .
C7 C 0.2853(9) -0.1116(4) 0.6526(4) 0.0382(16) Uani 1 1 d . . . . .
H7 H 0.247194 -0.171483 0.662090 0.046 Uiso 1 1 calc R U . . .
C8 C 0.2376(10) -0.0737(5) 0.5792(5) 0.0463(19) Uani 1 1 d . . . . .
H8 H 0.164911 -0.106681 0.537468 0.056 Uiso 1 1 calc R U . . .
C9 C 0.2970(10) 0.0128(5) 0.5672(4) 0.0482(19) Uani 1 1 d . . . . .
C10 C 0.4042(9) 0.0616(5) 0.6250(4) 0.0412(17) Uani 1 1 d . . . . .
H10 H 0.444462 0.120597 0.613928 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4552(8) 0.0258(4) 0.7000(4) 0.0288(14) Uani 1 1 d . . . . .
C12 C 0.9110(8) 0.0764(4) 0.8159(4) 0.0303(14) Uani 1 1 d . . . . .
C13 C 0.8702(8) 0.1429(4) 0.8730(4) 0.0316(14) Uani 1 1 d . . . . .
C14 C 0.7760(8) 0.2151(4) 0.8277(5) 0.0401(18) Uani 1 1 d . . . . .
C15 C 0.7573(8) 0.1965(4) 0.7460(4) 0.0328(15) Uani 1 1 d . . . . .
C16 C 0.8486(8) 0.1124(4) 0.7398(4) 0.0313(15) Uani 1 1 d . . . . .
C17 C 1.0164(8) -0.0103(4) 0.8384(4) 0.0384(16) Uani 1 1 d . . . . .
H17A H 1.007687 -0.049318 0.792137 0.058 Uiso 1 1 calc R U . . .
H17B H 0.965273 -0.042292 0.878558 0.058 Uiso 1 1 calc R U . . .
H17C H 1.144649 0.004334 0.859141 0.058 Uiso 1 1 calc R U . . .
C18 C 0.9356(10) 0.1393(6) 0.9600(4) 0.057(2) Uani 1 1 d . . . . .
H18A H 1.051982 0.171704 0.974118 0.085 Uiso 1 1 calc R U . . .
H18B H 0.952326 0.075751 0.976914 0.085 Uiso 1 1 calc R U . . .
H18C H 0.845219 0.168162 0.985983 0.085 Uiso 1 1 calc R U . . .
C19 C 0.7081(10) 0.3008(5) 0.8622(6) 0.059(2) Uani 1 1 d . . . . .
H19A H 0.688680 0.287965 0.915221 0.089 Uiso 1 1 calc R U . . .
H19B H 0.592846 0.320338 0.829167 0.089 Uiso 1 1 calc R U . . .
H19C H 0.798989 0.349260 0.864404 0.089 Uiso 1 1 calc R U . . .
C20 C 0.6744(9) 0.2609(5) 0.6816(5) 0.053(2) Uani 1 1 d . . . . .
H20A H 0.680509 0.233908 0.630658 0.079 Uiso 1 1 calc R U . . .
H20B H 0.741939 0.318434 0.687705 0.079 Uiso 1 1 calc R U . . .
H20C H 0.546695 0.272305 0.684365 0.079 Uiso 1 1 calc R U . . .
C21 C 0.8852(10) 0.0712(5) 0.6657(5) 0.0445(18) Uani 1 1 d . . . . .
H21A H 1.006101 0.090080 0.657916 0.067 Uiso 1 1 calc R U . . .
H21B H 0.792364 0.091799 0.621248 0.067 Uiso 1 1 calc R U . . .
H21C H 0.881074 0.004722 0.669364 0.067 Uiso 1 1 calc R U . . .


_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 C11 2.050(6) . ?
Ir1 N1 2.100(5) . ?
Ir1 C16 2.153(6) . ?
Ir1 C15 2.158(6) . ?
Ir1 C12 2.160(6) . ?
Ir1 C14 2.224(6) . ?
Ir1 C13 2.256(6) . ?
Ir1 Cl1 2.4001(16) . ?
F1 C9 1.341(8) . ?
N1 C1 1.334(8) . ?
N1 C5 1.374(8) . ?
C1 C2 1.384(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.455(9) . ?
C6 C11 1.396(8) . ?
C6 C7 1.404(9) . ?
C7 C8 1.375(10) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(10) . ?
C8 H8 0.9500 . ?
C9 C10 1.361(10) . ?
C10 C11 1.390(9) . ?
C10 H10 0.9500 . ?
C12 C16 1.417(9) . ?
C12 C13 1.468(8) . ?
C12 C17 1.509(8) . ?
C13 C14 1.423(9) . ?
C13 C18 1.499(9) . ?
C14 C15 1.429(9) . ?
C14 C19 1.525(9) . ?
C15 C16 1.426(8) . ?
C15 C20 1.504(9) . ?
C16 C21 1.499(10) . ?
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 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C11 Ir1 N1 77.9(2) . . ?
C11 Ir1 C16 97.3(2) . . ?
N1 Ir1 C16 128.8(2) . . ?
C11 Ir1 C15 106.2(2) . . ?
N1 Ir1 C15 166.4(2) . . ?
C16 Ir1 C15 38.6(2) . . ?
C11 Ir1 C12 121.8(2) . . ?
N1 Ir1 C12 101.8(2) . . ?
C16 Ir1 C12 38.3(2) . . ?
C15 Ir1 C12 64.9(2) . . ?
C11 Ir1 C14 142.0(3) . . ?
N1 Ir1 C14 140.1(2) . . ?
C16 Ir1 C14 63.0(2) . . ?
C15 Ir1 C14 38.0(3) . . ?
C12 Ir1 C14 63.3(2) . . ?
C11 Ir1 C13 159.9(2) . . ?
N1 Ir1 C13 107.8(2) . . ?
C16 Ir1 C13 63.9(2) . . ?
C15 Ir1 C13 64.1(2) . . ?
C12 Ir1 C13 38.8(2) . . ?
C14 Ir1 C13 37.0(2) . . ?
C11 Ir1 Cl1 87.74(17) . . ?
N1 Ir1 Cl1 85.87(13) . . ?
C16 Ir1 Cl1 145.33(17) . . ?
C15 Ir1 Cl1 107.03(17) . . ?
C12 Ir1 Cl1 150.39(17) . . ?
C14 Ir1 Cl1 92.38(16) . . ?
C13 Ir1 Cl1 111.64(16) . . ?
C1 N1 C5 118.9(5) . . ?
C1 N1 Ir1 124.8(4) . . ?
C5 N1 Ir1 116.3(4) . . ?
N1 C1 C2 123.6(6) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C1 C2 C3 117.4(6) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 H2 121.3 . . ?
C4 C3 C2 120.4(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.5(6) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 120.2(6) . . ?
N1 C5 C6 114.1(5) . . ?
C4 C5 C6 125.6(6) . . ?
C11 C6 C7 121.4(6) . . ?
C11 C6 C5 115.0(5) . . ?
C7 C6 C5 123.5(6) . . ?
C8 C7 C6 119.3(6) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 118.9(7) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
F1 C9 C10 119.4(7) . . ?
F1 C9 C8 118.2(7) . . ?
C10 C9 C8 122.4(7) . . ?
C9 C10 C11 120.5(6) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C6 117.4(6) . . ?
C10 C11 Ir1 126.1(5) . . ?
C6 C11 Ir1 116.5(4) . . ?
C16 C12 C13 108.0(5) . . ?
C16 C12 C17 128.2(6) . . ?
C13 C12 C17 123.6(6) . . ?
C16 C12 Ir1 70.6(3) . . ?
C13 C12 Ir1 74.1(3) . . ?
C17 C12 Ir1 125.2(4) . . ?
C14 C13 C12 105.6(6) . . ?
C14 C13 C18 127.8(6) . . ?
C12 C13 C18 126.2(6) . . ?
C14 C13 Ir1 70.3(3) . . ?
C12 C13 Ir1 67.1(3) . . ?
C18 C13 Ir1 132.3(5) . . ?
C13 C14 C15 110.4(5) . . ?
C13 C14 C19 124.5(7) . . ?
C15 C14 C19 125.1(7) . . ?
C13 C14 Ir1 72.7(3) . . ?
C15 C14 Ir1 68.5(3) . . ?
C19 C14 Ir1 126.5(4) . . ?
C16 C15 C14 106.6(6) . . ?
C16 C15 C20 128.5(7) . . ?
C14 C15 C20 124.6(6) . . ?
C16 C15 Ir1 70.5(3) . . ?
C14 C15 Ir1 73.5(4) . . ?
C20 C15 Ir1 126.2(4) . . ?
C12 C16 C15 109.2(6) . . ?
C12 C16 C21 124.8(6) . . ?
C15 C16 C21 125.9(7) . . ?
C12 C16 Ir1 71.1(3) . . ?
C15 C16 Ir1 70.9(3) . . ?
C21 C16 Ir1 127.4(5) . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C14 C19 H19A 109.5 . . ?
C14 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C14 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         1.735
_refine_diff_density_min         -1.997
_refine_diff_density_rms         0.160

