# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1553345'
_audit_update_record             
;
2017-05-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 Cl2 Co N4'
_chemical_formula_weight         330.08

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.3443(4)
_cell_length_b                   9.1002(7)
_cell_length_c                   10.2856(7)
_cell_angle_alpha                94.070(6)
_cell_angle_beta                 107.603(5)
_cell_angle_gamma                91.867(5)
_cell_volume                     652.54(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2436
_cell_measurement_theta_min      2.9040
_cell_measurement_theta_max      31.8700

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             334
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.710
_shelx_estimated_absorpt_T_min   0.527
_shelx_estimated_absorpt_T_max   0.821
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83035
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_reflns_number            6923
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         32.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4228
_reflns_number_gt                3633
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0282P)²+0.0650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4228
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0685
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.0931(2) -0.19534(19) 0.84803(17) 0.0222(3) Uani 1 1 d . . . . .
H1 H 0.0678 -0.1717 0.9322 0.027 Uiso 1 1 calc R U . . .
C2 C 0.0663(2) -0.3400(2) 0.79248(19) 0.0273(4) Uani 1 1 d . . . . .
H2 H 0.0238 -0.4151 0.8380 0.033 Uiso 1 1 calc R U . . .
C3 C 0.1019(3) -0.3739(2) 0.6702(2) 0.0298(4) Uani 1 1 d . . . . .
H3 H 0.0852 -0.4729 0.6307 0.036 Uiso 1 1 calc R U . . .
C4 C 0.1626(2) -0.26209(19) 0.60500(18) 0.0247(3) Uani 1 1 d . . . . .
H4 H 0.1858 -0.2831 0.5198 0.030 Uiso 1 1 calc R U . . .
C5 C 0.1883(2) -0.12000(17) 0.66647(15) 0.0171(3) Uani 1 1 d . . . . .
C6 C 0.26034(19) 0.00719(17) 0.60940(15) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.2537(2) 0.00579(19) 0.47428(15) 0.0196(3) Uani 1 1 d . . . . .
H7 H 0.2085 -0.0791 0.4120 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3171(2) 0.1361(2) 0.43378(16) 0.0228(3) Uani 1 1 d . . . . .
H8 H 0.3063 0.1404 0.3397 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4021(2) 0.24415(17) 0.65137(15) 0.0173(3) Uani 1 1 d . . . . .
C10 C 0.5474(3) 0.3466(2) 0.88710(17) 0.0280(4) Uani 1 1 d . . . . .
H10A H 0.4413 0.3712 0.9224 0.042 Uiso 1 1 calc R U . . .
H10B H 0.6581 0.4149 0.9320 0.042 Uiso 1 1 calc R U . . .
H10C H 0.5818 0.2454 0.9059 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5595(3) 0.4898(2) 0.6918(2) 0.0282(4) Uani 1 1 d . . . . .
H11A H 0.6815 0.4709 0.6751 0.042 Uiso 1 1 calc R U . . .
H11B H 0.5781 0.5731 0.7612 0.042 Uiso 1 1 calc R U . . .
H11C H 0.4658 0.5135 0.6065 0.042 Uiso 1 1 calc R U . . .
N1 N 0.15368(17) -0.08743(15) 0.78643(13) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.32973(17) 0.12771(14) 0.69899(13) 0.0161(2) Uani 1 1 d . . . . .
N3 N 0.39115(19) 0.25348(17) 0.51823(14) 0.0226(3) Uani 1 1 d . . . . .
N4 N 0.48957(19) 0.35871(15) 0.74012(14) 0.0214(3) Uani 1 1 d . . . . .
Cl1 Cl 0.35819(6) 0.11755(6) 1.09098(4) 0.02920(10) Uani 1 1 d . . . . .
Cl2 Cl -0.01100(6) 0.27627(5) 0.81465(4) 0.02668(9) Uani 1 1 d . . . . .
Co1 Co 0.23081(3) 0.12329(2) 0.86559(2) 0.01805(6) 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 N1 1.340(2) . ?
C1 C2 1.381(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.377(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.3483(19) . ?
C5 C6 1.486(2) . ?
C6 N2 1.3593(19) . ?
C6 C7 1.375(2) . ?
C7 C8 1.395(2) . ?
C7 H7 0.9500 . ?
C8 N3 1.318(2) . ?
C8 H8 0.9500 . ?
C9 N4 1.342(2) . ?
C9 N2 1.3562(19) . ?
C9 N3 1.3563(19) . ?
C10 N4 1.455(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N4 1.461(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 Co1 2.0223(14) . ?
N2 Co1 2.0559(13) . ?
Cl1 Co1 2.2273(5) . ?
Cl2 Co1 2.2513(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
N1 C1 C2 121.75(16) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.03(17) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.45(17) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.69(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 121.63(15) . . ?
N1 C5 C6 114.88(13) . . ?
C4 C5 C6 123.47(14) . . ?
N2 C6 C7 121.64(15) . . ?
N2 C6 C5 115.61(13) . . ?
C7 C6 C5 122.73(14) . . ?
C6 C7 C8 116.28(15) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
N3 C8 C7 123.90(15) . . ?
N3 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
N4 C9 N2 118.74(14) . . ?
N4 C9 N3 117.07(15) . . ?
N2 C9 N3 124.19(15) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 N1 C5 119.44(14) . . ?
C1 N1 Co1 126.25(11) . . ?
C5 N1 Co1 113.92(11) . . ?
C9 N2 C6 117.15(13) . . ?
C9 N2 Co1 129.01(11) . . ?
C6 N2 Co1 110.94(10) . . ?
C8 N3 C9 116.45(15) . . ?
C9 N4 C10 121.17(14) . . ?
C9 N4 C11 120.41(14) . . ?
C10 N4 C11 117.56(14) . . ?
N1 Co1 N2 81.60(5) . . ?
N1 Co1 Cl1 107.04(4) . . ?
N2 Co1 Cl1 136.70(4) . . ?
N1 Co1 Cl2 113.84(4) . . ?
N2 Co1 Cl2 102.50(4) . . ?
Cl1 Co1 Cl2 111.428(18) . . ?

_refine_diff_density_max         0.535
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1541493'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 Cl Co F6 N4 P'
_chemical_formula_weight         546.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2836(5)
_cell_length_b                   11.4551(9)
_cell_length_c                   12.2705(7)
_cell_angle_alpha                103.762(6)
_cell_angle_beta                 93.088(5)
_cell_angle_gamma                104.169(6)
_cell_volume                     1088.71(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3096
_cell_measurement_theta_min      3.7250
_cell_measurement_theta_max      62.5550

_exptl_crystal_description       plate
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.404
_exptl_crystal_size_min          0.171
_exptl_absorpt_coefficient_mu    8.620
_shelx_estimated_absorpt_T_min   0.102
_shelx_estimated_absorpt_T_max   0.320
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_reflns_number            6935
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.735
_diffrn_reflns_theta_max         62.805
_diffrn_reflns_theta_full        62.805
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             3463
_reflns_number_gt                3071
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0553P)²+0.2943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3463
_refine_ls_number_parameters     300
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.4144(4) -0.0437(3) 0.2282(3) 0.0295(7) Uani 1 1 d . . . . .
H1 H 0.3106 -0.0622 0.2583 0.035 Uiso 1 1 calc R U . . .
C2 C 0.5072(4) -0.1306(3) 0.2121(3) 0.0341(7) Uani 1 1 d . . . . .
H2 H 0.4675 -0.2074 0.2312 0.041 Uiso 1 1 calc R U . . .
C3 C 0.6571(4) -0.1046(3) 0.1684(3) 0.0352(8) Uani 1 1 d . . . . .
H3 H 0.7253 -0.1611 0.1611 0.042 Uiso 1 1 calc R U . . .
C4 C 0.7079(4) 0.0048(3) 0.1351(3) 0.0310(7) Uani 1 1 d . . . . .
H4 H 0.8086 0.0226 0.1013 0.037 Uiso 1 1 calc R U . . .
C5 C 0.6089(4) 0.0879(3) 0.1520(2) 0.0250(6) Uani 1 1 d . . . . .
C6 C 0.6352(4) 0.1988(3) 0.1087(2) 0.0250(6) Uani 1 1 d . . . . .
C7 C 0.7632(4) 0.2392(3) 0.0478(3) 0.0296(7) Uani 1 1 d . . . . .
H7 H 0.8505 0.1991 0.0340 0.036 Uiso 1 1 calc R U . . .
C8 C 0.7569(4) 0.3418(3) 0.0079(3) 0.0339(7) Uani 1 1 d . . . . .
H8 H 0.8497 0.3778 -0.0266 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5027(4) 0.3428(3) 0.0695(3) 0.0278(7) Uani 1 1 d . . . . .
C10 C 0.4238(4) 0.3897(3) 0.3459(3) 0.0291(7) Uani 1 1 d . . . . .
C11 C 0.5141(4) 0.3146(3) 0.3884(3) 0.0326(7) Uani 1 1 d . . . . .
C12 C 0.3929(5) 0.2138(3) 0.4128(3) 0.0331(7) Uani 1 1 d . . . . .
C13 C 0.2303(4) 0.2194(3) 0.3769(3) 0.0303(7) Uani 1 1 d . . . . .
C14 C 0.2494(4) 0.3295(3) 0.3360(3) 0.0286(7) Uani 1 1 d . . . . .
C15 C 0.5024(5) 0.5121(3) 0.3229(3) 0.0422(8) Uani 1 1 d . . . . .
H15A H 0.4176 0.5385 0.2831 0.063 Uiso 1 1 calc R U . . .
H15B H 0.5930 0.5035 0.2760 0.063 Uiso 1 1 calc R U . . .
H15C H 0.5480 0.5746 0.3946 0.063 Uiso 1 1 calc R U . . .
C16 C 0.6994(5) 0.3441(4) 0.4137(4) 0.0523(11) Uani 1 1 d . . . . .
H16A H 0.7531 0.4016 0.3705 0.078 Uiso 1 1 calc R U . . .
H16B H 0.7352 0.2671 0.3925 0.078 Uiso 1 1 calc R U . . .
H16C H 0.7322 0.3829 0.4947 0.078 Uiso 1 1 calc R U . . .
C17 C 0.4325(6) 0.1232(4) 0.4726(3) 0.0550(11) Uani 1 1 d . . . . .
H17A H 0.4392 0.1576 0.5544 0.083 Uiso 1 1 calc R U . . .
H17B H 0.5402 0.1079 0.4537 0.083 Uiso 1 1 calc R U . . .
H17C H 0.3441 0.0447 0.4490 0.083 Uiso 1 1 calc R U . . .
C18 C 0.0686(5) 0.1316(4) 0.3838(3) 0.0443(9) Uani 1 1 d . . . . .
H18A H 0.0856 0.0491 0.3799 0.066 Uiso 1 1 calc R U . . .
H18B H -0.0134 0.1257 0.3207 0.066 Uiso 1 1 calc R U . . .
H18C H 0.0267 0.1622 0.4554 0.066 Uiso 1 1 calc R U . . .
C19 C 0.1079(5) 0.3756(4) 0.2983(3) 0.0432(9) Uani 1 1 d . . . . .
H19A H 0.0593 0.4134 0.3644 0.065 Uiso 1 1 calc R U . . .
H19B H 0.0219 0.3057 0.2488 0.065 Uiso 1 1 calc R U . . .
H19C H 0.1497 0.4381 0.2569 0.065 Uiso 1 1 calc R U . . .
N1 N 0.4670(3) 0.0657(2) 0.2025(2) 0.0256(5) Uani 1 1 d . . . . .
N2 N 0.5115(3) 0.2568(2) 0.1266(2) 0.0235(5) Uani 1 1 d . . . . .
N3 N 0.6290(3) 0.3922(3) 0.0152(2) 0.0313(6) Uani 1 1 d . . . . .
N4 N 0.3636(4) 0.3811(3) 0.0670(3) 0.0380(7) Uani 1 1 d D . . . .
H4A H 0.272(4) 0.330(3) 0.080(4) 0.046 Uiso 1 1 d D U . . .
H4B H 0.359(5) 0.443(3) 0.038(3) 0.046 Uiso 1 1 d D U . . .
F1 F 0.1704(3) 0.6637(2) 0.2625(2) 0.0616(7) Uani 1 1 d . . . . .
F2 F 0.0167(4) 0.7667(3) 0.1869(2) 0.0709(8) Uani 1 1 d . . . . .
F3 F 0.1124(4) 0.8302(2) 0.3726(2) 0.0665(7) Uani 1 1 d . . . . .
F4 F -0.1642(3) 0.7432(3) 0.3174(3) 0.0690(8) Uani 1 1 d . . . . .
F5 F -0.0118(3) 0.6393(2) 0.3915(2) 0.0533(6) Uani 1 1 d . . . . .
F6 F -0.1030(4) 0.5731(3) 0.2079(3) 0.0799(9) Uani 1 1 d . . . . .
P1 P 0.00084(12) 0.70232(8) 0.28846(8) 0.0381(2) Uani 1 1 d . . . . .
Cl1 Cl 0.14418(9) 0.11522(7) 0.11078(6) 0.0329(2) Uani 1 1 d . . . . .
Co1 Co 0.37019(6) 0.20756(4) 0.24053(4) 0.02254(15) 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 N1 1.340(4) . ?
C1 C2 1.385(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.355(4) . ?
C5 C6 1.463(5) . ?
C6 N2 1.352(4) . ?
C6 C7 1.381(5) . ?
C7 C8 1.386(5) . ?
C7 H7 0.9500 . ?
C8 N3 1.323(4) . ?
C8 H8 0.9500 . ?
C9 N4 1.331(4) . ?
C9 N3 1.350(4) . ?
C9 N2 1.351(4) . ?
C10 C14 1.425(5) . ?
C10 C11 1.434(5) . ?
C10 C15 1.493(5) . ?
C10 Co1 2.103(3) . ?
C11 C12 1.436(5) . ?
C11 C16 1.487(5) . ?
C11 Co1 2.052(3) . ?
C12 C13 1.415(5) . ?
C12 C17 1.492(5) . ?
C12 Co1 2.095(3) . ?
C13 C14 1.441(5) . ?
C13 C18 1.485(5) . ?
C13 Co1 2.083(3) . ?
C14 C19 1.493(5) . ?
C14 Co1 2.087(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 . ?
N1 Co1 1.954(3) . ?
N2 Co1 1.967(2) . ?
N4 H4A 0.881(19) . ?
N4 H4B 0.876(19) . ?
F1 P1 1.598(2) . ?
F2 P1 1.588(3) . ?
F3 P1 1.606(3) . ?
F4 P1 1.582(3) . ?
F5 P1 1.594(2) . ?
F6 P1 1.580(3) . ?
Cl1 Co1 2.2510(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.8(3) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 C6 113.5(3) . . ?
C4 C5 C6 124.7(3) . . ?
N2 C6 C7 120.9(3) . . ?
N2 C6 C5 113.0(3) . . ?
C7 C6 C5 125.9(3) . . ?
C6 C7 C8 116.2(3) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
N3 C8 C7 123.6(3) . . ?
N3 C8 H8 118.2 . . ?
C7 C8 H8 118.2 . . ?
N4 C9 N3 118.4(3) . . ?
N4 C9 N2 118.5(3) . . ?
N3 C9 N2 123.0(3) . . ?
C14 C10 C11 107.7(3) . . ?
C14 C10 C15 127.4(3) . . ?
C11 C10 C15 124.9(3) . . ?
C14 C10 Co1 69.51(18) . . ?
C11 C10 Co1 67.88(18) . . ?
C15 C10 Co1 130.4(2) . . ?
C10 C11 C12 107.5(3) . . ?
C10 C11 C16 125.8(3) . . ?
C12 C11 C16 126.4(3) . . ?
C10 C11 Co1 71.76(18) . . ?
C12 C11 Co1 71.38(18) . . ?
C16 C11 Co1 127.1(2) . . ?
C13 C12 C11 108.8(3) . . ?
C13 C12 C17 125.9(4) . . ?
C11 C12 C17 125.2(4) . . ?
C13 C12 Co1 69.72(17) . . ?
C11 C12 Co1 68.11(18) . . ?
C17 C12 Co1 130.9(2) . . ?
C12 C13 C14 107.4(3) . . ?
C12 C13 C18 126.8(3) . . ?
C14 C13 C18 125.8(3) . . ?
C12 C13 Co1 70.67(18) . . ?
C14 C13 Co1 69.94(17) . . ?
C18 C13 Co1 126.5(2) . . ?
C10 C14 C13 108.4(3) . . ?
C10 C14 C19 126.6(3) . . ?
C13 C14 C19 124.8(3) . . ?
C10 C14 Co1 70.73(17) . . ?
C13 C14 Co1 69.61(17) . . ?
C19 C14 Co1 128.8(2) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
C1 N1 C5 118.9(3) . . ?
C1 N1 Co1 126.8(2) . . ?
C5 N1 Co1 114.1(2) . . ?
C9 N2 C6 117.9(3) . . ?
C9 N2 Co1 128.1(2) . . ?
C6 N2 Co1 113.9(2) . . ?
C8 N3 C9 116.8(3) . . ?
C9 N4 H4A 116(3) . . ?
C9 N4 H4B 121(3) . . ?
H4A N4 H4B 121(4) . . ?
F6 P1 F4 91.97(18) . . ?
F6 P1 F2 91.97(19) . . ?
F4 P1 F2 91.41(15) . . ?
F6 P1 F5 88.91(16) . . ?
F4 P1 F5 89.11(14) . . ?
F2 P1 F5 178.97(17) . . ?
F6 P1 F1 89.53(16) . . ?
F4 P1 F1 178.37(18) . . ?
F2 P1 F1 89.15(14) . . ?
F5 P1 F1 90.31(14) . . ?
F6 P1 F3 177.20(19) . . ?
F4 P1 F3 90.15(16) . . ?
F2 P1 F3 89.81(16) . . ?
F5 P1 F3 89.30(15) . . ?
F1 P1 F3 88.33(15) . . ?
N1 Co1 N2 80.40(10) . . ?
N1 Co1 C11 102.40(12) . . ?
N2 Co1 C11 101.78(12) . . ?
N1 Co1 C13 117.16(12) . . ?
N2 Co1 C13 160.78(12) . . ?
C11 Co1 C13 68.20(13) . . ?
N1 Co1 C14 157.14(12) . . ?
N2 Co1 C14 121.16(12) . . ?
C11 Co1 C14 67.81(13) . . ?
C13 Co1 C14 40.44(13) . . ?
N1 Co1 C12 92.16(12) . . ?
N2 Co1 C12 139.22(13) . . ?
C11 Co1 C12 40.51(14) . . ?
C13 Co1 C12 39.61(14) . . ?
C14 Co1 C12 66.78(13) . . ?
N1 Co1 C10 140.77(12) . . ?
N2 Co1 C10 94.10(11) . . ?
C11 Co1 C10 40.36(14) . . ?
C13 Co1 C10 67.50(13) . . ?
C14 Co1 C10 39.77(13) . . ?
C12 Co1 C10 66.91(13) . . ?
N1 Co1 Cl1 93.75(8) . . ?
N2 Co1 Cl1 92.33(8) . . ?
C11 Co1 Cl1 160.04(10) . . ?
C13 Co1 Cl1 94.08(10) . . ?
C14 Co1 Cl1 92.85(9) . . ?
C12 Co1 Cl1 128.31(10) . . ?
C10 Co1 Cl1 125.39(10) . . ?

_refine_diff_density_max         0.527
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1541497'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 B Cl F4 Ir N3'
_chemical_formula_weight         606.85

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'
B B 0.0013 0.0007 '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                   8.5377(2)
_cell_length_b                   21.2436(4)
_cell_length_c                   11.3841(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.301(2)
_cell_angle_gamma                90
_cell_volume                     2058.94(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    11116
_cell_measurement_theta_min      3.3610
_cell_measurement_theta_max      32.1700

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_F_000             1168
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.294
_exptl_crystal_size_mid          0.261
_exptl_crystal_size_min          0.178
_exptl_absorpt_coefficient_mu    6.660
_shelx_estimated_absorpt_T_min   0.245
_shelx_estimated_absorpt_T_max   0.384
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.223
_exptl_absorpt_correction_T_max  0.415
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_reflns_number            24366
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.881
_diffrn_reflns_theta_max         32.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6909
_reflns_number_gt                6001
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0277P)²+1.4915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6909
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0692
_refine_ls_wR_factor_gt          0.0664
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_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
C1 C 1.0676(5) 0.38077(17) 0.9365(4) 0.0336(8) Uani 1 1 d . . . . .
H1 H 1.1505 0.3578 0.9054 0.040 Uiso 1 1 calc R U . . .
C2 C 1.0651(5) 0.38722(18) 1.0577(4) 0.0381(9) Uani 1 1 d . . . . .
H2 H 1.1437 0.3679 1.1091 0.046 Uiso 1 1 calc R U . . .
C3 C 0.9487(5) 0.4216(2) 1.1019(4) 0.0390(9) Uani 1 1 d . . . . .
H3 H 0.9451 0.4259 1.1847 0.047 Uiso 1 1 calc R U . . .
C4 C 0.8356(5) 0.45022(18) 1.0269(3) 0.0319(8) Uani 1 1 d . . . . .
H4 H 0.7551 0.4750 1.0569 0.038 Uiso 1 1 calc R U . . .
C5 C 0.8428(4) 0.44182(15) 0.9063(3) 0.0239(6) Uani 1 1 d . . . . .
C6 C 0.7375(4) 0.47197(15) 0.8165(3) 0.0216(6) Uani 1 1 d . . . . .
C7 C 0.6207(4) 0.51479(17) 0.8385(3) 0.0278(7) Uani 1 1 d . . . . .
H7 H 0.6000 0.5257 0.9168 0.033 Uiso 1 1 calc R U . . .
C8 C 0.5359(4) 0.54098(17) 0.7433(3) 0.0307(8) Uani 1 1 d . . . . .
H8 H 0.4532 0.5693 0.7572 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6792(4) 0.48677(16) 0.6169(3) 0.0265(7) Uani 1 1 d . . . . .
H9 H 0.7013 0.4772 0.5383 0.032 Uiso 1 1 calc R U . . .
C10 C 1.0741(4) 0.30838(16) 0.6396(3) 0.0275(7) Uani 1 1 d . . . . .
C11 C 0.9341(4) 0.28817(15) 0.6924(3) 0.0242(7) Uani 1 1 d . . . . .
C12 C 0.8016(4) 0.30981(14) 0.6201(3) 0.0223(6) Uani 1 1 d . . . . .
C13 C 0.8582(4) 0.34171(14) 0.5190(3) 0.0235(6) Uani 1 1 d . . . . .
C14 C 1.0252(4) 0.33995(15) 0.5318(3) 0.0264(7) Uani 1 1 d . . . . .
C15 C 1.2400(5) 0.2927(2) 0.6817(5) 0.0410(10) Uani 1 1 d . . . . .
H15A H 1.2781 0.2584 0.6340 0.062 Uiso 1 1 calc R U . . .
H15B H 1.2438 0.2796 0.7644 0.062 Uiso 1 1 calc R U . . .
H15C H 1.3065 0.3299 0.6744 0.062 Uiso 1 1 calc R U . . .
C16 C 0.9269(5) 0.24996(17) 0.8008(4) 0.0323(8) Uani 1 1 d . . . . .
H16A H 0.8379 0.2639 0.8438 0.048 Uiso 1 1 calc R U . . .
H16B H 1.0246 0.2552 0.8507 0.048 Uiso 1 1 calc R U . . .
H16C H 0.9133 0.2055 0.7795 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6327(4) 0.29764(18) 0.6376(4) 0.0302(8) Uani 1 1 d . . . . .
H17A H 0.5982 0.2595 0.5946 0.045 Uiso 1 1 calc R U . . .
H17B H 0.5693 0.3335 0.6080 0.045 Uiso 1 1 calc R U . . .
H17C H 0.6197 0.2919 0.7217 0.045 Uiso 1 1 calc R U . . .
C18 C 0.7606(5) 0.36616(18) 0.4144(3) 0.0332(8) Uani 1 1 d . . . . .
H18A H 0.8103 0.4038 0.3842 0.050 Uiso 1 1 calc R U . . .
H18B H 0.6556 0.3769 0.4376 0.050 Uiso 1 1 calc R U . . .
H18C H 0.7518 0.3338 0.3529 0.050 Uiso 1 1 calc R U . . .
C19 C 1.1307(5) 0.3662(2) 0.4453(4) 0.0397(10) Uani 1 1 d . . . . .
H19A H 1.1481 0.3343 0.3853 0.060 Uiso 1 1 calc R U . . .
H19B H 1.2315 0.3779 0.4862 0.060 Uiso 1 1 calc R U . . .
H19C H 1.0818 0.4035 0.4075 0.060 Uiso 1 1 calc R U . . .
N1 N 0.9552(3) 0.40634(13) 0.8623(3) 0.0244(6) Uani 1 1 d . . . . .
N2 N 0.7652(3) 0.45750(12) 0.7035(3) 0.0221(5) Uani 1 1 d . . . . .
N3 N 0.5649(4) 0.52823(15) 0.6316(3) 0.0309(7) Uani 1 1 d . . . . .
B1 B 0.5073(6) 0.3387(2) 0.9907(4) 0.0336(9) Uani 1 1 d . . . . .
F1 F 0.3724(4) 0.30424(16) 0.9816(4) 0.0969(16) Uani 1 1 d . . . . .
F2 F 0.5580(5) 0.34620(14) 1.1058(3) 0.0720(10) Uani 1 1 d . . . . .
F3 F 0.6202(5) 0.30851(18) 0.9355(3) 0.0836(12) Uani 1 1 d . . . . .
F4 F 0.4767(4) 0.39783(12) 0.9391(3) 0.0526(7) Uani 1 1 d . . . . .
Cl1 Cl 1.12152(12) 0.47455(4) 0.66833(10) 0.0362(2) Uani 1 1 d . . . . .
Ir1 Ir 0.93932(2) 0.38966(2) 0.68153(2) 0.02041(4) 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 N1 1.345(5) . ?
C1 C2 1.388(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.360(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.381(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.390(5) . ?
C4 H4 0.9500 . ?
C5 N1 1.347(4) . ?
C5 C6 1.458(5) . ?
C6 N2 1.361(4) . ?
C6 C7 1.386(5) . ?
C7 C8 1.375(5) . ?
C7 H7 0.9500 . ?
C8 N3 1.341(5) . ?
C8 H8 0.9500 . ?
C9 N3 1.334(4) . ?
C9 N2 1.338(4) . ?
C9 H9 0.9500 . ?
C10 C14 1.433(5) . ?
C10 C11 1.444(5) . ?
C10 C15 1.498(5) . ?
C10 Ir1 2.149(3) . ?
C11 C12 1.425(5) . ?
C11 C16 1.482(5) . ?
C11 Ir1 2.160(3) . ?
C12 C13 1.449(5) . ?
C12 C17 1.493(5) . ?
C12 Ir1 2.151(3) . ?
C13 C14 1.423(5) . ?
C13 C18 1.494(5) . ?
C13 Ir1 2.179(3) . ?
C14 C19 1.491(5) . ?
C14 Ir1 2.178(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 . ?
N1 Ir1 2.083(3) . ?
N2 Ir1 2.099(3) . ?
B1 F3 1.351(5) . ?
B1 F2 1.359(6) . ?
B1 F1 1.362(6) . ?
B1 F4 1.403(5) . ?
Cl1 Ir1 2.3936(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.4(4) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 119.2(4) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 118.3(4) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 113.8(3) . . ?
C4 C5 C6 124.5(3) . . ?
N2 C6 C7 119.8(3) . . ?
N2 C6 C5 114.9(3) . . ?
C7 C6 C5 125.1(3) . . ?
C8 C7 C6 117.8(3) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
N3 C8 C7 122.8(3) . . ?
N3 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
N3 C9 N2 125.5(3) . . ?
N3 C9 H9 117.3 . . ?
N2 C9 H9 117.3 . . ?
C14 C10 C11 107.4(3) . . ?
C14 C10 C15 125.9(3) . . ?
C11 C10 C15 126.4(3) . . ?
C14 C10 Ir1 71.79(19) . . ?
C11 C10 Ir1 70.86(18) . . ?
C15 C10 Ir1 128.1(3) . . ?
C12 C11 C10 108.0(3) . . ?
C12 C11 C16 125.3(3) . . ?
C10 C11 C16 126.7(3) . . ?
C12 C11 Ir1 70.35(18) . . ?
C10 C11 Ir1 69.99(19) . . ?
C16 C11 Ir1 126.6(2) . . ?
C11 C12 C13 108.2(3) . . ?
C11 C12 C17 126.9(3) . . ?
C13 C12 C17 124.8(3) . . ?
C11 C12 Ir1 71.06(19) . . ?
C13 C12 Ir1 71.50(18) . . ?
C17 C12 Ir1 127.1(2) . . ?
C14 C13 C12 107.3(3) . . ?
C14 C13 C18 125.8(3) . . ?
C12 C13 C18 126.6(3) . . ?
C14 C13 Ir1 70.9(2) . . ?
C12 C13 Ir1 69.41(19) . . ?
C18 C13 Ir1 129.5(2) . . ?
C13 C14 C10 109.0(3) . . ?
C13 C14 C19 124.9(4) . . ?
C10 C14 C19 126.0(3) . . ?
C13 C14 Ir1 70.96(19) . . ?
C10 C14 Ir1 69.55(19) . . ?
C19 C14 Ir1 126.2(3) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
C1 N1 C5 119.2(3) . . ?
C1 N1 Ir1 122.9(3) . . ?
C5 N1 Ir1 117.9(2) . . ?
C9 N2 C6 117.8(3) . . ?
C9 N2 Ir1 125.9(2) . . ?
C6 N2 Ir1 116.3(2) . . ?
C9 N3 C8 116.2(3) . . ?
F3 B1 F2 108.5(4) . . ?
F3 B1 F1 109.8(4) . . ?
F2 B1 F1 110.1(4) . . ?
F3 B1 F4 110.3(4) . . ?
F2 B1 F4 109.5(4) . . ?
F1 B1 F4 108.6(4) . . ?
N1 Ir1 N2 76.09(11) . . ?
N1 Ir1 C10 111.11(13) . . ?
N2 Ir1 C10 166.98(13) . . ?
N1 Ir1 C12 116.69(12) . . ?
N2 Ir1 C12 101.86(11) . . ?
C10 Ir1 C12 65.34(13) . . ?
N1 Ir1 C11 96.50(12) . . ?
N2 Ir1 C11 131.35(11) . . ?
C10 Ir1 C11 39.15(12) . . ?
C12 Ir1 C11 38.59(13) . . ?
N1 Ir1 C14 148.74(13) . . ?
N2 Ir1 C14 135.16(13) . . ?
C10 Ir1 C14 38.66(14) . . ?
C12 Ir1 C14 64.60(12) . . ?
C11 Ir1 C14 64.58(13) . . ?
N1 Ir1 C13 155.72(12) . . ?
N2 Ir1 C13 103.85(12) . . ?
C10 Ir1 C13 64.98(14) . . ?
C12 Ir1 C13 39.09(12) . . ?
C11 Ir1 C13 64.88(13) . . ?
C14 Ir1 C13 38.12(13) . . ?
N1 Ir1 Cl1 86.52(8) . . ?
N2 Ir1 Cl1 87.68(8) . . ?
C10 Ir1 Cl1 103.29(10) . . ?
C12 Ir1 Cl1 156.31(9) . . ?
C11 Ir1 Cl1 140.52(9) . . ?
C14 Ir1 Cl1 93.30(9) . . ?
C13 Ir1 Cl1 117.75(9) . . ?

_refine_diff_density_max         2.493
_refine_diff_density_min         -1.448
_refine_diff_density_rms         0.136

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1541496'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H23 Cl N4 Rh, F6 P'
_chemical_formula_sum            'C19 H23 Cl F6 N4 P Rh'
_chemical_formula_weight         590.74

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'
P P 0.1023 0.0942 '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'
Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2257(3)
_cell_length_b                   11.4475(4)
_cell_length_c                   12.6623(4)
_cell_angle_alpha                102.000(3)
_cell_angle_beta                 93.609(3)
_cell_angle_gamma                105.079(3)
_cell_volume                     1117.44(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6046
_cell_measurement_theta_min      3.39
_cell_measurement_theta_max      32.18

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.020
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_T_max  0.749
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            12798
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.208
_diffrn_reflns_theta_max         32.329
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7228
_reflns_number_gt                6605
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    SUPERFLIP
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 A second orientation of the anion is apparent through Q1, Q7, Q8, Q9,
 Q11 and Q12. However, the attempt to refine this minor disorder 
 component (occupancy ca. 7%) was unsuccessful and did not yield a
 more satisfying overall result, which is why it was ultimately
 discarded.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+1.0127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7228
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.0718(3) 0.54819(19) 0.26502(18) 0.0265(4) Uani 1 1 d . . . . .
H1 H 0.1698 0.5652 0.2286 0.032 Uiso 1 1 calc R U . . .
C2 C -0.0182(3) 0.6356(2) 0.28419(19) 0.0297(4) Uani 1 1 d . . . . .
H2 H 0.0173 0.7110 0.2610 0.036 Uiso 1 1 calc R U . . .
C3 C -0.1602(3) 0.6116(2) 0.33736(19) 0.0298(4) Uani 1 1 d . . . . .
H3 H -0.2269 0.6686 0.3483 0.036 Uiso 1 1 calc R U . . .
C4 C -0.2043(3) 0.5034(2) 0.37467(18) 0.0251(4) Uani 1 1 d . . . . .
H4 H -0.2989 0.4868 0.4142 0.030 Uiso 1 1 calc R U . . .
C5 C -0.1085(2) 0.41994(18) 0.35349(15) 0.0192(3) Uani 1 1 d . . . . .
C6 C -0.1331(2) 0.30815(18) 0.39789(15) 0.0203(3) Uani 1 1 d . . . . .
C7 C -0.2572(3) 0.2706(2) 0.46208(18) 0.0274(4) Uani 1 1 d . . . . .
H7 H -0.3399 0.3139 0.4789 0.033 Uiso 1 1 calc R U . . .
C8 C -0.2542(3) 0.1657(2) 0.50065(19) 0.0310(5) Uani 1 1 d . . . . .
H8 H -0.3451 0.1318 0.5380 0.037 Uiso 1 1 calc R U . . .
C9 C -0.0081(3) 0.15679(19) 0.42993(17) 0.0240(4) Uani 1 1 d . . . . .
C10 C -0.0076(3) 0.1816(2) 0.10032(17) 0.0280(4) Uani 1 1 d . . . . .
C11 C 0.0810(3) 0.10773(18) 0.14736(17) 0.0241(4) Uani 1 1 d . . . . .
C12 C 0.2581(3) 0.16873(18) 0.16077(16) 0.0226(4) Uani 1 1 d . . . . .
C13 C 0.2813(3) 0.27994(19) 0.11916(16) 0.0242(4) Uani 1 1 d . . . . .
C14 C 0.1183(3) 0.2847(2) 0.07940(17) 0.0284(4) Uani 1 1 d . . . . .
C15 C -0.1950(3) 0.1481(3) 0.0679(2) 0.0465(7) Uani 1 1 d . . . . .
H15A H -0.2325 0.2239 0.0806 0.070 Uiso 1 1 calc R U . . .
H15B H -0.2537 0.0925 0.1114 0.070 Uiso 1 1 calc R U . . .
H15C H -0.2216 0.1061 -0.0094 0.070 Uiso 1 1 calc R U . . .
C16 C -0.0026(4) -0.0139(2) 0.1732(2) 0.0387(6) Uani 1 1 d . . . . .
H16A H 0.0812 -0.0402 0.2140 0.058 Uiso 1 1 calc R U . . .
H16B H -0.0495 -0.0767 0.1055 0.058 Uiso 1 1 calc R U . . .
H16C H -0.0942 -0.0043 0.2172 0.058 Uiso 1 1 calc R U . . .
C17 C 0.3987(3) 0.1254(2) 0.2042(2) 0.0353(5) Uani 1 1 d . . . . .
H17A H 0.3549 0.0675 0.2497 0.053 Uiso 1 1 calc R U . . .
H17B H 0.4873 0.1971 0.2480 0.053 Uiso 1 1 calc R U . . .
H17C H 0.4465 0.0832 0.1436 0.053 Uiso 1 1 calc R U . . .
C18 C 0.4490(3) 0.3694(2) 0.1155(2) 0.0381(6) Uani 1 1 d . . . . .
H18A H 0.4976 0.3381 0.0505 0.057 Uiso 1 1 calc R U . . .
H18B H 0.5262 0.3779 0.1806 0.057 Uiso 1 1 calc R U . . .
H18C H 0.4327 0.4507 0.1132 0.057 Uiso 1 1 calc R U . . .
C19 C 0.0834(5) 0.3778(3) 0.0211(2) 0.0476(7) Uani 1 1 d . . . . .
H19A H 0.1714 0.4571 0.0473 0.071 Uiso 1 1 calc R U . . .
H19B H -0.0277 0.3898 0.0349 0.071 Uiso 1 1 calc R U . . .
H19C H 0.0835 0.3477 -0.0572 0.071 Uiso 1 1 calc R U . . .
N1 N 0.0257(2) 0.44068(15) 0.29598(13) 0.0202(3) Uani 1 1 d . . . . .
N2 N -0.0157(2) 0.24585(15) 0.37580(14) 0.0208(3) Uani 1 1 d . . . . .
N3 N -0.1308(3) 0.11053(18) 0.48794(15) 0.0284(4) Uani 1 1 d . . . . .
N4 N 0.1280(3) 0.1129(2) 0.42535(18) 0.0343(4) Uani 1 1 d . . . . .
F1 F 0.6671(3) 0.7560(2) 0.1814(2) 0.0677(6) Uani 1 1 d . . . . .
F2 F 0.5172(2) 0.86174(15) 0.10765(15) 0.0473(4) Uani 1 1 d . . . . .
F3 F 0.3310(2) 0.83440(17) 0.23084(17) 0.0546(5) Uani 1 1 d . . . . .
F4 F 0.4825(3) 0.7302(2) 0.30677(18) 0.0699(6) Uani 1 1 d . . . . .
F5 F 0.6088(3) 0.9249(2) 0.28447(18) 0.0717(6) Uani 1 1 d . . . . .
F6 F 0.3869(3) 0.66971(16) 0.12693(17) 0.0629(6) Uani 1 1 d . . . . .
P1 P 0.50104(9) 0.79640(6) 0.20754(6) 0.03328(13) Uani 1 1 d . . . . .
Cl1 Cl 0.36419(7) 0.39237(6) 0.39098(4) 0.03258(12) Uani 1 1 d . . . . .
Rh1 Rh 0.13166(2) 0.29242(2) 0.25247(2) 0.01755(5) Uani 1 1 d . . . . .
H1N H 0.225(4) 0.163(3) 0.407(2) 0.039(8) Uiso 1 1 d . . . . .
H2N H 0.132(5) 0.044(4) 0.461(3) 0.068(11) Uiso 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 N1 1.337(3) . ?
C1 C2 1.384(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.357(2) . ?
C5 C6 1.474(3) . ?
C6 N2 1.352(2) . ?
C6 C7 1.381(3) . ?
C7 C8 1.393(3) . ?
C7 H7 0.9500 . ?
C8 N3 1.329(3) . ?
C8 H8 0.9500 . ?
C9 N4 1.340(3) . ?
C9 N3 1.347(3) . ?
C9 N2 1.353(3) . ?
C10 C14 1.437(3) . ?
C10 C11 1.440(3) . ?
C10 C15 1.497(3) . ?
C10 Rh1 2.141(2) . ?
C11 C12 1.424(3) . ?
C11 C16 1.496(3) . ?
C11 Rh1 2.1717(19) . ?
C12 C13 1.449(3) . ?
C12 C17 1.490(3) . ?
C12 Rh1 2.1605(19) . ?
C13 C14 1.421(3) . ?
C13 C18 1.498(3) . ?
C13 Rh1 2.154(2) . ?
C14 C19 1.491(3) . ?
C14 Rh1 2.169(2) . ?
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 . ?
N1 Rh1 2.0943(16) . ?
N2 Rh1 2.1074(17) . ?
N4 H1N 0.93(3) . ?
N4 H2N 0.99(4) . ?
F1 P1 1.5846(19) . ?
F2 P1 1.5937(17) . ?
F3 P1 1.5960(18) . ?
F4 P1 1.5922(19) . ?
F5 P1 1.586(2) . ?
F6 P1 1.6068(19) . ?
Cl1 Rh1 2.3766(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
N1 C1 C2 122.3(2) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.1(2) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.69(18) . . ?
N1 C5 C6 114.39(17) . . ?
C4 C5 C6 123.74(18) . . ?
N2 C6 C7 120.91(19) . . ?
N2 C6 C5 114.14(17) . . ?
C7 C6 C5 124.85(19) . . ?
C6 C7 C8 116.2(2) . . ?
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
N3 C8 C7 123.4(2) . . ?
N3 C8 H8 118.3 . . ?
C7 C8 H8 118.3 . . ?
N4 C9 N3 118.76(19) . . ?
N4 C9 N2 118.24(19) . . ?
N3 C9 N2 123.0(2) . . ?
C14 C10 C11 107.34(19) . . ?
C14 C10 C15 126.6(2) . . ?
C11 C10 C15 125.7(2) . . ?
C14 C10 Rh1 71.60(12) . . ?
C11 C10 Rh1 71.65(12) . . ?
C15 C10 Rh1 127.27(16) . . ?
C12 C11 C10 108.20(18) . . ?
C12 C11 C16 127.1(2) . . ?
C10 C11 C16 124.6(2) . . ?
C12 C11 Rh1 70.38(11) . . ?
C10 C11 Rh1 69.33(11) . . ?
C16 C11 Rh1 127.43(16) . . ?
C11 C12 C13 108.04(18) . . ?
C11 C12 C17 127.3(2) . . ?
C13 C12 C17 124.6(2) . . ?
C11 C12 Rh1 71.24(11) . . ?
C13 C12 Rh1 70.12(11) . . ?
C17 C12 Rh1 126.57(15) . . ?
C14 C13 C12 107.54(19) . . ?
C14 C13 C18 127.1(2) . . ?
C12 C13 C18 125.3(2) . . ?
C14 C13 Rh1 71.42(12) . . ?
C12 C13 Rh1 70.63(11) . . ?
C18 C13 Rh1 125.20(15) . . ?
C13 C14 C10 108.76(19) . . ?
C13 C14 C19 125.8(2) . . ?
C10 C14 C19 125.4(2) . . ?
C13 C14 Rh1 70.21(12) . . ?
C10 C14 Rh1 69.45(12) . . ?
C19 C14 Rh1 128.33(16) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
C1 N1 C5 118.65(17) . . ?
C1 N1 Rh1 125.23(14) . . ?
C5 N1 Rh1 115.93(13) . . ?
C6 N2 C9 118.22(17) . . ?
C6 N2 Rh1 115.66(13) . . ?
C9 N2 Rh1 126.04(14) . . ?
C8 N3 C9 116.98(19) . . ?
C9 N4 H1N 116.7(19) . . ?
C9 N4 H2N 119(2) . . ?
H1N N4 H2N 122(3) . . ?
F1 P1 F5 91.80(13) . . ?
F1 P1 F4 91.47(11) . . ?
F5 P1 F4 91.91(14) . . ?
F1 P1 F2 88.96(10) . . ?
F5 P1 F2 88.62(12) . . ?
F4 P1 F2 179.31(13) . . ?
F1 P1 F3 178.40(13) . . ?
F5 P1 F3 89.69(12) . . ?
F4 P1 F3 89.05(11) . . ?
F2 P1 F3 90.51(10) . . ?
F1 P1 F6 90.01(13) . . ?
F5 P1 F6 177.32(14) . . ?
F4 P1 F6 90.02(13) . . ?
F2 P1 F6 89.43(11) . . ?
F3 P1 F6 88.48(11) . . ?
N1 Rh1 N2 76.04(6) . . ?
N1 Rh1 C10 106.05(8) . . ?
N2 Rh1 C10 107.26(8) . . ?
N1 Rh1 C13 121.33(7) . . ?
N2 Rh1 C13 162.04(7) . . ?
C10 Rh1 C13 65.49(8) . . ?
N1 Rh1 C12 160.20(7) . . ?
N2 Rh1 C12 123.02(7) . . ?
C10 Rh1 C12 65.29(8) . . ?
C13 Rh1 C12 39.25(8) . . ?
N1 Rh1 C14 97.16(7) . . ?
N2 Rh1 C14 143.10(8) . . ?
C10 Rh1 C14 38.95(9) . . ?
C13 Rh1 C14 38.37(9) . . ?
C12 Rh1 C14 64.63(8) . . ?
N1 Rh1 C11 142.34(7) . . ?
N2 Rh1 C11 98.70(7) . . ?
C10 Rh1 C11 39.02(8) . . ?
C13 Rh1 C11 65.03(8) . . ?
C12 Rh1 C11 38.38(8) . . ?
C14 Rh1 C11 64.55(8) . . ?
N1 Rh1 Cl1 90.74(5) . . ?
N2 Rh1 Cl1 87.65(5) . . ?
C10 Rh1 Cl1 159.63(6) . . ?
C13 Rh1 Cl1 96.10(6) . . ?
C12 Rh1 Cl1 95.09(6) . . ?
C14 Rh1 Cl1 129.05(7) . . ?
C11 Rh1 Cl1 126.65(6) . . ?

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
N1 C1 C2 C3 0.2(4) . . . . ?
C1 C2 C3 C4 3.0(3) . . . . ?
C2 C3 C4 C5 -2.7(3) . . . . ?
C3 C4 C5 N1 -0.9(3) . . . . ?
C3 C4 C5 C6 173.90(19) . . . . ?
N1 C5 C6 N2 1.2(2) . . . . ?
C4 C5 C6 N2 -173.91(18) . . . . ?
N1 C5 C6 C7 177.64(19) . . . . ?
C4 C5 C6 C7 2.5(3) . . . . ?
N2 C6 C7 C8 -0.7(3) . . . . ?
C5 C6 C7 C8 -176.83(19) . . . . ?
C6 C7 C8 N3 7.1(3) . . . . ?
C14 C10 C11 C12 3.3(2) . . . . ?
C15 C10 C11 C12 176.9(2) . . . . ?
Rh1 C10 C11 C12 -59.88(14) . . . . ?
C14 C10 C11 C16 -174.9(2) . . . . ?
C15 C10 C11 C16 -1.3(3) . . . . ?
Rh1 C10 C11 C16 121.9(2) . . . . ?
C14 C10 C11 Rh1 63.14(14) . . . . ?
C15 C10 C11 Rh1 -123.2(2) . . . . ?
C10 C11 C12 C13 -1.5(2) . . . . ?
C16 C11 C12 C13 176.6(2) . . . . ?
Rh1 C11 C12 C13 -60.76(13) . . . . ?
C10 C11 C12 C17 -178.6(2) . . . . ?
C16 C11 C12 C17 -0.5(4) . . . . ?
Rh1 C11 C12 C17 122.2(2) . . . . ?
C10 C11 C12 Rh1 59.23(14) . . . . ?
C16 C11 C12 Rh1 -122.6(2) . . . . ?
C11 C12 C13 C14 -0.8(2) . . . . ?
C17 C12 C13 C14 176.4(2) . . . . ?
Rh1 C12 C13 C14 -62.27(14) . . . . ?
C11 C12 C13 C18 -178.5(2) . . . . ?
C17 C12 C13 C18 -1.4(3) . . . . ?
Rh1 C12 C13 C18 120.0(2) . . . . ?
C11 C12 C13 Rh1 61.47(14) . . . . ?
C17 C12 C13 Rh1 -121.3(2) . . . . ?
C12 C13 C14 C10 2.8(2) . . . . ?
C18 C13 C14 C10 -179.5(2) . . . . ?
Rh1 C13 C14 C10 -58.93(14) . . . . ?
C12 C13 C14 C19 -174.6(2) . . . . ?
C18 C13 C14 C19 3.0(4) . . . . ?
Rh1 C13 C14 C19 123.6(2) . . . . ?
C12 C13 C14 Rh1 61.76(13) . . . . ?
C18 C13 C14 Rh1 -120.6(2) . . . . ?
C11 C10 C14 C13 -3.8(2) . . . . ?
C15 C10 C14 C13 -177.4(2) . . . . ?
Rh1 C10 C14 C13 59.39(14) . . . . ?
C11 C10 C14 C19 173.7(2) . . . . ?
C15 C10 C14 C19 0.1(4) . . . . ?
Rh1 C10 C14 C19 -123.1(2) . . . . ?
C11 C10 C14 Rh1 -63.17(14) . . . . ?
C15 C10 C14 Rh1 123.2(2) . . . . ?
C2 C1 N1 C5 -3.8(3) . . . . ?
C2 C1 N1 Rh1 171.02(17) . . . . ?
C4 C5 N1 C1 4.1(3) . . . . ?
C6 C5 N1 C1 -171.15(18) . . . . ?
C4 C5 N1 Rh1 -171.17(15) . . . . ?
C6 C5 N1 Rh1 13.6(2) . . . . ?
C7 C6 N2 C9 -9.0(3) . . . . ?
C5 C6 N2 C9 167.59(17) . . . . ?
C7 C6 N2 Rh1 168.09(16) . . . . ?
C5 C6 N2 Rh1 -15.3(2) . . . . ?
N4 C9 N2 C6 -166.6(2) . . . . ?
N3 C9 N2 C6 13.4(3) . . . . ?
N4 C9 N2 Rh1 16.7(3) . . . . ?
N3 C9 N2 Rh1 -163.34(16) . . . . ?
C7 C8 N3 C9 -3.3(3) . . . . ?
N4 C9 N3 C8 172.7(2) . . . . ?
N2 C9 N3 C8 -7.3(3) . . . . ?

_refine_diff_density_max         1.548
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.090

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1541495'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H23 Cl F6 N2 P Rh'
_chemical_formula_weight         574.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Rh Rh 0.0927 3.6045 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           31
_space_group_name_H-M_alt        'P m n 21'
_space_group_name_Hall           'P 2ac -2'

_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, z+1/2'
'-x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   12.9323(3)
_cell_length_b                   8.1971(2)
_cell_length_c                   10.4445(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1107.19(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4569
_cell_measurement_theta_min      5.3920
_cell_measurement_theta_max      62.6260

_exptl_crystal_description       'transparent prism'
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.213
_exptl_absorpt_coefficient_mu    8.592
_shelx_estimated_absorpt_T_min   0.139
_shelx_estimated_absorpt_T_max   0.262
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_T_max  0.967
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_reflns_number            6409
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.397
_diffrn_reflns_theta_max         62.686
_diffrn_reflns_theta_full        62.686
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_point_group_measured_fraction_full 0.813
_reflns_number_total             1515
_reflns_number_gt                1498
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.533
_reflns_Friedel_fraction_max     0.602
_reflns_Friedel_fraction_full    0.603

_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0487P)²+0.0459P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 509 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.018(12)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1515
_refine_ls_number_parameters     159
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0637
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.074
_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
C1 C 0.7052(4) 0.8017(7) 0.9549(6) 0.0268(11) Uani 1 1 d . . . . .
H1 H 0.7360 0.7686 0.8765 0.032 Uiso 1 1 calc R U . . .
C2 C 0.7684(4) 0.8496(7) 1.0541(6) 0.0311(12) Uani 1 1 d . . . . .
H2 H 0.8414 0.8476 1.0448 0.037 Uiso 1 1 calc R U . . .
C3 C 0.7236(4) 0.9010(6) 1.1682(6) 0.0327(12) Uani 1 1 d . . . . .
H3 H 0.7654 0.9362 1.2377 0.039 Uiso 1 1 calc R U . . .
C4 C 0.6166(4) 0.8999(6) 1.1785(5) 0.0273(11) Uani 1 1 d . . . . .
H4 H 0.5843 0.9335 1.2558 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5569(4) 0.8495(6) 1.0754(5) 0.0230(11) Uani 1 1 d . . . . .
C6 C 0.5547(4) 0.4877(5) 0.7849(5) 0.0226(11) Uani 1 1 d . . . . .
C7 C 0.5891(4) 0.5913(7) 0.6808(6) 0.0290(12) Uani 1 1 d . . . . .
C8 C 0.5000 0.6514(9) 0.6185(8) 0.0349(19) Uani 1 2 d S T P . .
C9 C 0.6210(5) 0.3952(7) 0.8742(7) 0.0468(17) Uani 1 1 d . . . . .
H9A H 0.6196 0.2793 0.8514 0.070 Uiso 1 1 calc R U . . .
H9B H 0.5953 0.4091 0.9618 0.070 Uiso 1 1 calc R U . . .
H9C H 0.6921 0.4359 0.8687 0.070 Uiso 1 1 calc R U . . .
C10 C 0.6994(5) 0.6135(10) 0.6392(8) 0.059(2) Uani 1 1 d . . . . .
H10A H 0.7102 0.7268 0.6125 0.089 Uiso 1 1 calc R U . . .
H10B H 0.7141 0.5405 0.5672 0.089 Uiso 1 1 calc R U . . .
H10C H 0.7457 0.5877 0.7106 0.089 Uiso 1 1 calc R U . . .
C11 C 0.5000 0.7622(12) 0.5036(13) 0.073(5) Uani 1 2 d DS T P . .
H11A H 0.5000 0.711(18) 0.419(7) 0.110 Uiso 1 2 d DS U P . .
H11B H 0.551(6) 0.849(9) 0.515(12) 0.110 Uiso 1 1 d D U . . .
N1 N 0.6017(3) 0.7999(5) 0.9649(4) 0.0204(9) Uani 1 1 d . . . . .
F1 F 0.5000 0.1768(7) 0.3799(7) 0.0705(19) Uani 1 2 d S T P . .
F2 F 0.5862(3) 0.4170(6) 0.3875(6) 0.0839(18) Uani 1 1 d . . . . .
F3 F 0.5852(5) 0.2620(5) 0.2135(8) 0.088(2) Uani 1 1 d . . . . .
F4 F 0.5000 0.5019(8) 0.2167(7) 0.088(3) Uani 1 2 d S T P . .
P1 P 0.5000 0.3423(2) 0.3008(2) 0.0288(5) Uani 1 2 d S T P . .
Cl1 Cl 0.5000 1.0153(2) 0.75511(19) 0.0280(4) Uani 1 2 d S T P . .
Rh1 Rh 0.5000 0.73356(5) 0.81602(7) 0.0170(2) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.343(7) . ?
C1 C2 1.377(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(7) . ?
C4 H4 0.9500 . ?
C5 N1 1.354(7) . ?
C5 C5 1.472(11) 3_655 ?
C6 C6 1.415(9) 3_655 ?
C6 C7 1.449(8) . ?
C6 C9 1.476(8) . ?
C6 Rh1 2.161(4) . ?
C7 C8 1.412(8) . ?
C7 C10 1.502(7) . ?
C7 Rh1 2.164(5) . ?
C8 C7 1.412(8) 3_655 ?
C8 C11 1.505(14) . ?
C8 Rh1 2.170(8) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.98(3) . ?
C11 H11B 0.98(3) . ?
N1 Rh1 2.108(5) . ?
F1 P1 1.588(7) . ?
F2 P1 1.562(4) . ?
F3 P1 1.574(6) . ?
F4 P1 1.576(7) . ?
P1 F2 1.562(4) 3_655 ?
P1 F3 1.574(6) 3_655 ?
Cl1 Rh1 2.3957(17) . ?
Rh1 N1 2.108(5) 3_655 ?
Rh1 C6 2.161(4) 3_655 ?
Rh1 C7 2.164(5) 3_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.4(6) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 119.0(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 118.7(5) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 119.8(5) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 120.9(5) . . ?
N1 C5 C5 115.3(3) . 3_655 ?
C4 C5 C5 123.8(3) . 3_655 ?
C6 C6 C7 107.9(3) 3_655 . ?
C6 C6 C9 125.5(4) 3_655 . ?
C7 C6 C9 126.7(5) . . ?
C6 C6 Rh1 70.88(12) 3_655 . ?
C7 C6 Rh1 70.5(3) . . ?
C9 C6 Rh1 125.0(4) . . ?
C8 C7 C6 107.5(5) . . ?
C8 C7 C10 126.8(6) . . ?
C6 C7 C10 125.4(6) . . ?
C8 C7 Rh1 71.2(4) . . ?
C6 C7 Rh1 70.3(3) . . ?
C10 C7 Rh1 129.0(4) . . ?
C7 C8 C7 109.4(7) . 3_655 ?
C7 C8 C11 125.3(4) . . ?
C7 C8 C11 125.3(4) 3_655 . ?
C7 C8 Rh1 70.7(4) . . ?
C7 C8 Rh1 70.7(4) 3_655 . ?
C11 C8 Rh1 124.8(6) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 118(10) . . ?
C8 C11 H11B 110(7) . . ?
H11A C11 H11B 115(9) . . ?
C1 N1 C5 119.3(5) . . ?
C1 N1 Rh1 124.6(4) . . ?
C5 N1 Rh1 116.1(3) . . ?
F2 P1 F2 91.1(4) . 3_655 ?
F2 P1 F3 178.3(3) . 3_655 ?
F2 P1 F3 90.0(3) 3_655 3_655 ?
F2 P1 F3 90.0(3) . . ?
F2 P1 F3 178.3(3) 3_655 . ?
F3 P1 F3 88.8(6) 3_655 . ?
F2 P1 F4 89.9(3) . . ?
F2 P1 F4 89.9(3) 3_655 . ?
F3 P1 F4 91.4(3) 3_655 . ?
F3 P1 F4 91.4(3) . . ?
F2 P1 F1 91.9(3) . . ?
F2 P1 F1 91.9(3) 3_655 . ?
F3 P1 F1 86.8(3) 3_655 . ?
F3 P1 F1 86.8(3) . . ?
F4 P1 F1 177.5(4) . . ?
N1 Rh1 N1 77.2(2) . 3_655 ?
N1 Rh1 C6 98.48(16) . . ?
N1 Rh1 C6 123.79(17) 3_655 . ?
N1 Rh1 C6 123.79(17) . 3_655 ?
N1 Rh1 C6 98.48(16) 3_655 3_655 ?
C6 Rh1 C6 38.2(2) . 3_655 ?
N1 Rh1 C7 106.76(18) . . ?
N1 Rh1 C7 162.3(2) 3_655 . ?
C6 Rh1 C7 39.1(2) . . ?
C6 Rh1 C7 64.74(19) 3_655 . ?
N1 Rh1 C7 162.31(19) . 3_655 ?
N1 Rh1 C7 106.76(18) 3_655 3_655 ?
C6 Rh1 C7 64.74(19) . 3_655 ?
C6 Rh1 C7 39.1(2) 3_655 3_655 ?
C7 Rh1 C7 64.3(3) . 3_655 ?
N1 Rh1 C8 141.38(12) . . ?
N1 Rh1 C8 141.38(12) 3_655 . ?
C6 Rh1 C8 64.4(2) . . ?
C6 Rh1 C8 64.4(2) 3_655 . ?
C7 Rh1 C8 38.02(19) . . ?
C7 Rh1 C8 38.02(19) 3_655 . ?
N1 Rh1 Cl1 86.97(12) . . ?
N1 Rh1 Cl1 86.97(12) 3_655 . ?
C6 Rh1 Cl1 149.23(14) . . ?
C6 Rh1 Cl1 149.23(14) 3_655 . ?
C7 Rh1 Cl1 110.27(17) . . ?
C7 Rh1 Cl1 110.27(17) 3_655 . ?
C8 Rh1 Cl1 92.7(2) . . ?

_refine_diff_density_max         0.845
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1541494'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H25 Cl Co F6 N4 P'
_chemical_formula_weight         560.79

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'
P P 0.1023 0.0942 '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'
Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.3924(4)
_cell_length_b                   11.5244(5)
_cell_length_c                   13.1783(6)
_cell_angle_alpha                109.543(4)
_cell_angle_beta                 92.325(4)
_cell_angle_gamma                108.365(4)
_cell_volume                     1124.68(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4989
_cell_measurement_theta_min      3.1540
_cell_measurement_theta_max      31.9920

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.266
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.019
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92966
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_reflns_number            12700
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.842
_diffrn_reflns_theta_max         32.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.903
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7323
_reflns_number_gt                6463
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0306P)²+0.6012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7323
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0339
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C1 C 0.0491(2) 0.55838(14) 0.25135(12) 0.0230(3) Uani 1 1 d . . . . .
H1 H 0.1437 0.5809 0.2156 0.028 Uiso 1 1 calc R U . . .
C2 C -0.0546(2) 0.63343(16) 0.27012(13) 0.0283(3) Uani 1 1 d . . . . .
H2 H -0.0320 0.7059 0.2469 0.034 Uiso 1 1 calc R U . . .
C3 C -0.1915(2) 0.60164(16) 0.32307(13) 0.0286(3) Uani 1 1 d . . . . .
H3 H -0.2685 0.6483 0.3324 0.034 Uiso 1 1 calc R U . . .
C4 C -0.21492(19) 0.50092(15) 0.36227(12) 0.0234(3) Uani 1 1 d . . . . .
H4 H -0.3037 0.4810 0.4029 0.028 Uiso 1 1 calc R U . . .
C5 C -0.10645(17) 0.42994(13) 0.34108(11) 0.0178(2) Uani 1 1 d . . . . .
C6 C -0.10730(18) 0.32855(14) 0.38522(11) 0.0185(2) Uani 1 1 d . . . . .
C7 C -0.2194(2) 0.28591(15) 0.44980(12) 0.0244(3) Uani 1 1 d . . . . .
H7 H -0.3088 0.3189 0.4688 0.029 Uiso 1 1 calc R U . . .
C8 C -0.1931(2) 0.19146(16) 0.48525(13) 0.0278(3) Uani 1 1 d . . . . .
H8 H -0.2765 0.1511 0.5213 0.033 Uiso 1 1 calc R U . . .
C9 C 0.0531(2) 0.20967(15) 0.41614(12) 0.0220(3) Uani 1 1 d . . . . .
C10 C 0.2527(3) 0.1091(2) 0.46103(17) 0.0411(5) Uani 1 1 d . . . . .
H10A H 0.3100 0.1618 0.5364 0.062 Uiso 1 1 calc R U . . .
H10B H 0.3303 0.0724 0.4187 0.062 Uiso 1 1 calc R U . . .
H10C H 0.1512 0.0374 0.4605 0.062 Uiso 1 1 calc R U . . .
C11 C 0.24985(19) 0.19768(14) 0.15490(12) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.2632(2) 0.29975(14) 0.11158(11) 0.0209(3) Uani 1 1 d . . . . .
C13 C 0.0966(2) 0.29175(14) 0.07863(11) 0.0216(3) Uani 1 1 d . . . . .
C14 C -0.02183(19) 0.19019(14) 0.10582(11) 0.0201(3) Uani 1 1 d . . . . .
C15 C 0.07412(18) 0.12815(13) 0.14755(11) 0.0190(3) Uani 1 1 d . . . . .
C16 C 0.3970(2) 0.16719(17) 0.19120(15) 0.0293(3) Uani 1 1 d . . . . .
H16A H 0.3589 0.1060 0.2294 0.044 Uiso 1 1 calc R U . . .
H16B H 0.4845 0.2485 0.2406 0.044 Uiso 1 1 calc R U . . .
H16C H 0.4444 0.1270 0.1275 0.044 Uiso 1 1 calc R U . . .
C17 C 0.4251(2) 0.39157(17) 0.09881(14) 0.0312(4) Uani 1 1 d . . . . .
H17A H 0.4523 0.3535 0.0262 0.047 Uiso 1 1 calc R U . . .
H17B H 0.5174 0.4057 0.1546 0.047 Uiso 1 1 calc R U . . .
H17C H 0.4120 0.4757 0.1073 0.047 Uiso 1 1 calc R U . . .
C18 C 0.0482(3) 0.36709(18) 0.01804(14) 0.0349(4) Uani 1 1 d . . . . .
H18A H 0.1427 0.4495 0.0322 0.052 Uiso 1 1 calc R U . . .
H18B H -0.0525 0.3865 0.0424 0.052 Uiso 1 1 calc R U . . .
H18C H 0.0225 0.3148 -0.0604 0.052 Uiso 1 1 calc R U . . .
C19 C -0.2107(2) 0.14831(18) 0.08406(15) 0.0313(3) Uani 1 1 d . . . . .
H19A H -0.2530 0.0878 0.0082 0.047 Uiso 1 1 calc R U . . .
H19B H -0.2439 0.2256 0.0964 0.047 Uiso 1 1 calc R U . . .
H19C H -0.2596 0.1040 0.1332 0.047 Uiso 1 1 calc R U . . .
C20 C -0.0032(2) 0.00806(15) 0.17376(13) 0.0265(3) Uani 1 1 d . . . . .
H20A H -0.0557 -0.0679 0.1060 0.040 Uiso 1 1 calc R U . . .
H20B H -0.0902 0.0203 0.2196 0.040 Uiso 1 1 calc R U . . .
H20C H 0.0854 -0.0070 0.2130 0.040 Uiso 1 1 calc R U . . .
N1 N 0.02008(15) 0.45506(11) 0.28202(9) 0.0176(2) Uani 1 1 d . . . . .
N2 N 0.02202(15) 0.28311(12) 0.36131(9) 0.0180(2) Uani 1 1 d . . . . .
N3 N -0.05864(19) 0.15447(13) 0.47172(11) 0.0266(3) Uani 1 1 d . . . . .
N4 N 0.2029(2) 0.19168(15) 0.41279(12) 0.0283(3) Uani 1 1 d . . . . .
H4N H 0.276(3) 0.245(2) 0.3921(17) 0.031(5) Uiso 1 1 d . . . . .
F1 F 0.63747(17) 0.79107(15) 0.20481(14) 0.0595(4) Uani 1 1 d . . . . .
F2 F 0.51085(18) 0.86818(13) 0.10280(11) 0.0512(3) Uani 1 1 d . . . . .
F3 F 0.57679(19) 0.97534(13) 0.28335(12) 0.0638(4) Uani 1 1 d . . . . .
F4 F 0.30196(17) 0.86361(13) 0.20572(13) 0.0577(4) Uani 1 1 d . . . . .
F5 F 0.4298(2) 0.78758(16) 0.30836(11) 0.0643(4) Uani 1 1 d . . . . .
F6 F 0.36242(16) 0.68208(10) 0.12600(10) 0.0418(3) Uani 1 1 d . . . . .
P1 P 0.47149(6) 0.82842(4) 0.20625(4) 0.02732(9) Uani 1 1 d . . . . .
Cl1 Cl 0.37303(4) 0.46752(4) 0.36502(3) 0.02352(8) Uani 1 1 d . . . . .
Co1 Co 0.13584(2) 0.32696(2) 0.24569(2) 0.01520(5) 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 N1 1.3370(19) . ?
C1 C2 1.384(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3831(19) . ?
C4 H4 0.9500 . ?
C5 N1 1.3569(18) . ?
C5 C6 1.467(2) . ?
C6 N2 1.3516(18) . ?
C6 C7 1.3798(19) . ?
C7 C8 1.391(2) . ?
C7 H7 0.9500 . ?
C8 N3 1.325(2) . ?
C8 H8 0.9500 . ?
C9 N4 1.338(2) . ?
C9 N3 1.3460(19) . ?
C9 N2 1.3560(19) . ?
C10 N4 1.456(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C15 1.421(2) . ?
C11 C12 1.447(2) . ?
C11 C16 1.488(2) . ?
C11 Co1 2.0893(14) . ?
C12 C13 1.412(2) . ?
C12 C17 1.492(2) . ?
C12 Co1 2.0874(13) . ?
C13 C14 1.436(2) . ?
C13 C18 1.489(2) . ?
C13 Co1 2.0926(14) . ?
C14 C15 1.432(2) . ?
C14 C19 1.489(2) . ?
C14 Co1 2.0437(14) . ?
C15 C20 1.493(2) . ?
C15 Co1 2.0990(14) . ?
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 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 Co1 1.9547(12) . ?
N2 Co1 1.9542(12) . ?
N4 H4N 0.85(2) . ?
F1 P1 1.5812(13) . ?
F2 P1 1.5927(13) . ?
F3 P1 1.5854(13) . ?
F4 P1 1.5980(13) . ?
F5 P1 1.5852(14) . ?
F6 P1 1.5987(11) . ?
Cl1 Co1 2.2516(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.98(15) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.17(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.13(14) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.71(14) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 121.94(14) . . ?
N1 C5 C6 113.46(12) . . ?
C4 C5 C6 124.46(13) . . ?
N2 C6 C7 121.37(14) . . ?
N2 C6 C5 112.92(12) . . ?
C7 C6 C5 125.63(13) . . ?
C6 C7 C8 115.74(14) . . ?
C6 C7 H7 122.1 . . ?
C8 C7 H7 122.1 . . ?
N3 C8 C7 123.92(14) . . ?
N3 C8 H8 118.0 . . ?
C7 C8 H8 118.0 . . ?
N4 C9 N3 119.49(14) . . ?
N4 C9 N2 117.05(13) . . ?
N3 C9 N2 123.46(14) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C11 C12 107.73(13) . . ?
C15 C11 C16 127.50(14) . . ?
C12 C11 C16 124.59(14) . . ?
C15 C11 Co1 70.54(8) . . ?
C12 C11 Co1 69.66(8) . . ?
C16 C11 Co1 129.01(11) . . ?
C13 C12 C11 107.88(13) . . ?
C13 C12 C17 126.58(15) . . ?
C11 C12 C17 125.45(15) . . ?
C13 C12 Co1 70.46(8) . . ?
C11 C12 Co1 69.80(8) . . ?
C17 C12 Co1 127.79(10) . . ?
C12 C13 C14 108.44(13) . . ?
C12 C13 C18 126.64(15) . . ?
C14 C13 C18 124.76(15) . . ?
C12 C13 Co1 70.06(8) . . ?
C14 C13 Co1 67.86(8) . . ?
C18 C13 Co1 131.43(11) . . ?
C15 C14 C13 107.47(13) . . ?
C15 C14 C19 126.18(14) . . ?
C13 C14 C19 126.09(14) . . ?
C15 C14 Co1 71.86(8) . . ?
C13 C14 Co1 71.52(8) . . ?
C19 C14 Co1 126.64(11) . . ?
C11 C15 C14 108.23(12) . . ?
C11 C15 C20 127.53(14) . . ?
C14 C15 C20 124.21(14) . . ?
C11 C15 Co1 69.81(8) . . ?
C14 C15 Co1 67.71(8) . . ?
C20 C15 Co1 129.79(10) . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
C1 N1 C5 118.70(12) . . ?
C1 N1 Co1 126.85(10) . . ?
C5 N1 Co1 114.40(9) . . ?
C6 N2 C9 117.27(12) . . ?
C6 N2 Co1 114.67(9) . . ?
C9 N2 Co1 128.01(10) . . ?
C8 N3 C9 116.32(14) . . ?
C9 N4 C10 124.30(15) . . ?
C9 N4 H4N 113.7(15) . . ?
C10 N4 H4N 120.8(15) . . ?
F1 P1 F5 90.84(9) . . ?
F1 P1 F3 90.91(9) . . ?
F5 P1 F3 91.30(9) . . ?
F1 P1 F2 89.63(8) . . ?
F5 P1 F2 179.22(8) . . ?
F3 P1 F2 89.31(8) . . ?
F1 P1 F4 178.90(9) . . ?
F5 P1 F4 89.43(9) . . ?
F3 P1 F4 90.15(8) . . ?
F2 P1 F4 90.09(8) . . ?
F1 P1 F6 90.39(8) . . ?
F5 P1 F6 90.07(8) . . ?
F3 P1 F6 178.10(9) . . ?
F2 P1 F6 89.31(7) . . ?
F4 P1 F6 88.54(7) . . ?
N2 Co1 N1 80.84(5) . . ?
N2 Co1 C14 103.48(5) . . ?
N1 Co1 C14 99.73(5) . . ?
N2 Co1 C12 156.93(5) . . ?
N1 Co1 C12 121.10(6) . . ?
C14 Co1 C12 68.01(6) . . ?
N2 Co1 C11 116.61(5) . . ?
N1 Co1 C11 160.06(5) . . ?
C14 Co1 C11 68.00(6) . . ?
C12 Co1 C11 40.54(6) . . ?
N2 Co1 C13 142.41(6) . . ?
N1 Co1 C13 93.26(5) . . ?
C14 Co1 C13 40.62(6) . . ?
C12 Co1 C13 39.48(6) . . ?
C11 Co1 C13 67.10(6) . . ?
N2 Co1 C15 92.22(5) . . ?
N1 Co1 C15 136.87(5) . . ?
C14 Co1 C15 40.43(6) . . ?
C12 Co1 C15 67.17(6) . . ?
C11 Co1 C15 39.66(5) . . ?
C13 Co1 C15 66.99(6) . . ?
N2 Co1 Cl1 91.84(4) . . ?
N1 Co1 Cl1 93.02(4) . . ?
C14 Co1 Cl1 161.38(4) . . ?
C12 Co1 Cl1 93.80(4) . . ?
C11 Co1 Cl1 95.81(4) . . ?
C13 Co1 Cl1 125.66(5) . . ?
C15 Co1 Cl1 129.90(4) . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_14142o
_database_code_depnum_ccdc_archive 'CCDC 1541499'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H27 Cl2 Ir N4'
_chemical_formula_weight         598.57

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1530(5)
_cell_length_b                   11.1982(10)
_cell_length_c                   14.3416(8)
_cell_angle_alpha                78.653(6)
_cell_angle_beta                 84.574(5)
_cell_angle_gamma                83.732(6)
_cell_volume                     1272.51(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4463
_cell_measurement_theta_min      4.0570
_cell_measurement_theta_max      62.4930

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    12.177
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.27893
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7450
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.04
_diffrn_reflns_theta_max         62.43
_reflns_number_total             4018
_reflns_number_gt                3838
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0928P)²+14.2719P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4018
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1516
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1050(12) -0.0731(9) 0.2067(7) 0.030(2) Uani 1 1 d . . .
H1 H 1.0849 -0.1212 0.2683 0.036 Uiso 1 1 calc R . .
C2 C 1.2257(14) -0.1174(9) 0.1433(8) 0.036(2) Uani 1 1 d . . .
H2 H 1.2858 -0.1950 0.1611 0.043 Uiso 1 1 calc R . .
C3 C 1.2563(12) -0.0472(10) 0.0551(7) 0.032(2) Uani 1 1 d . . .
H3 H 1.3361 -0.0762 0.0100 0.039 Uiso 1 1 calc R . .
C4 C 1.1698(12) 0.0658(9) 0.0326(7) 0.030(2) Uani 1 1 d . . .
H4 H 1.1946 0.1175 -0.0269 0.036 Uiso 1 1 calc R . .
C5 C 1.0477(12) 0.1044(8) 0.0958(7) 0.0245(19) Uani 1 1 d . . .
C6 C 0.9414(11) 0.2198(8) 0.0785(7) 0.0220(18) Uani 1 1 d . . .
C7 C 0.8240(11) 0.2397(9) 0.1539(7) 0.0237(19) Uani 1 1 d . . .
C8 C 0.7360(11) 0.3535(8) 0.1364(6) 0.0237(19) Uani 1 1 d . . .
H8 H 0.6596 0.3782 0.1848 0.028 Uiso 1 1 calc R . .
C9 C 0.8670(11) 0.4002(8) -0.0181(7) 0.0230(19) Uani 1 1 d . . .
C10 C 0.9936(15) 0.4402(10) -0.1784(7) 0.036(2) Uani 1 1 d . . .
H10A H 1.0941 0.3938 -0.1533 0.054 Uiso 1 1 calc R . .
H10B H 1.0236 0.5126 -0.2248 0.054 Uiso 1 1 calc R . .
H10C H 0.9355 0.3886 -0.2097 0.054 Uiso 1 1 calc R . .
C11 C 0.7658(13) 0.5868(10) -0.1253(8) 0.035(2) Uani 1 1 d . . .
H11A H 0.6546 0.5603 -0.1230 0.052 Uiso 1 1 calc R . .
H11B H 0.7961 0.6309 -0.1896 0.052 Uiso 1 1 calc R . .
H11C H 0.7673 0.6409 -0.0794 0.052 Uiso 1 1 calc R . .
C12 C 0.5627(12) 0.0726(10) 0.2758(7) 0.031(2) Uani 1 1 d . . .
C13 C 0.5892(11) 0.1292(9) 0.3567(7) 0.027(2) Uani 1 1 d . . .
C14 C 0.6949(12) 0.0402(9) 0.4172(7) 0.029(2) Uani 1 1 d . . .
C15 C 0.7355(13) -0.0656(9) 0.3744(7) 0.029(2) Uani 1 1 d . . .
C16 C 0.6585(12) -0.0426(9) 0.2846(7) 0.027(2) Uani 1 1 d . . .
C17 C 0.4497(12) 0.1295(10) 0.1991(8) 0.034(2) Uani 1 1 d . . .
H17A H 0.4751 0.0887 0.1443 0.051 Uiso 1 1 calc R . .
H17B H 0.4657 0.2166 0.1792 0.051 Uiso 1 1 calc R . .
H17C H 0.3345 0.1205 0.2237 0.051 Uiso 1 1 calc R . .
C18 C 0.4998(15) 0.2444(11) 0.3795(9) 0.043(3) Uani 1 1 d . . .
H18A H 0.3890 0.2281 0.4088 0.064 Uiso 1 1 calc R . .
H18B H 0.4904 0.3057 0.3207 0.064 Uiso 1 1 calc R . .
H18C H 0.5613 0.2752 0.4239 0.064 Uiso 1 1 calc R . .
C19 C 0.7481(14) 0.0596(12) 0.5096(7) 0.040(3) Uani 1 1 d . . .
H19A H 0.6519 0.0613 0.5559 0.061 Uiso 1 1 calc R . .
H19B H 0.7976 0.1375 0.4994 0.061 Uiso 1 1 calc R . .
H19C H 0.8299 -0.0074 0.5340 0.061 Uiso 1 1 calc R . .
C20 C 0.8346(14) -0.1798(9) 0.4150(8) 0.036(2) Uani 1 1 d . . .
H20A H 0.8989 -0.1643 0.4651 0.054 Uiso 1 1 calc R . .
H20B H 0.9100 -0.2075 0.3646 0.054 Uiso 1 1 calc R . .
H20C H 0.7605 -0.2431 0.4423 0.054 Uiso 1 1 calc R . .
C21 C 0.6621(13) -0.1330(10) 0.2201(8) 0.035(2) Uani 1 1 d . . .
H21A H 0.5765 -0.1889 0.2433 0.053 Uiso 1 1 calc R . .
H21B H 0.7709 -0.1797 0.2192 0.053 Uiso 1 1 calc R . .
H21C H 0.6414 -0.0894 0.1554 0.053 Uiso 1 1 calc R . .
N1 N 1.0164(9) 0.0351(7) 0.1837(6) 0.0233(16) Uani 1 1 d . . .
N2 N 0.9618(10) 0.2940(7) -0.0046(5) 0.0244(16) Uani 1 1 d . . .
N3 N 0.7568(9) 0.4292(7) 0.0526(5) 0.0235(16) Uani 1 1 d . . .
H3N H 0.6970 0.5002 0.0431 0.028 Uiso 1 1 calc R . .
N4 N 0.8865(10) 0.4780(7) -0.1007(5) 0.0262(17) Uani 1 1 d . . .
Cl1 Cl 1.0180(3) 0.2060(2) 0.33142(16) 0.0317(5) Uani 1 1 d . . .
Cl2 Cl 0.5290(3) 0.6532(2) 0.0874(2) 0.0405(6) Uani 1 1 d . . .
Ir1 Ir 0.81900(4) 0.10217(3) 0.27193(2) 0.02155(19) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.339(12) . ?
C1 C2 1.394(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.374(14) . ?
C4 H4 0.9500 . ?
C5 N1 1.362(12) . ?
C5 C6 1.467(13) . ?
C6 N2 1.319(12) . ?
C6 C7 1.411(13) . ?
C7 C8 1.381(13) . ?
C7 Ir1 2.053(9) . ?
C8 N3 1.335(12) . ?
C8 H8 0.9500 . ?
C9 N4 1.332(12) . ?
C9 N2 1.337(12) . ?
C9 N3 1.355(13) . ?
C10 N4 1.450(14) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 N4 1.487(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C16 1.423(15) . ?
C12 C13 1.471(15) . ?
C12 C17 1.501(15) . ?
C12 Ir1 2.145(9) . ?
C13 C14 1.449(15) . ?
C13 C18 1.489(15) . ?
C13 Ir1 2.161(9) . ?
C14 C15 1.432(15) . ?
C14 C19 1.494(15) . ?
C14 Ir1 2.243(9) . ?
C15 C16 1.451(14) . ?
C15 C20 1.483(14) . ?
C15 Ir1 2.271(9) . ?
C16 C21 1.497(14) . ?
C16 Ir1 2.162(8) . ?
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 . ?
N1 Ir1 2.117(7) . ?
N3 H3N 0.8800 . ?
Cl1 Ir1 2.403(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.3(9) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 118.8(9) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.0(9) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 120.3(9) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
N1 C5 C4 120.9(9) . . ?
N1 C5 C6 113.5(8) . . ?
C4 C5 C6 125.6(9) . . ?
N2 C6 C7 126.1(8) . . ?
N2 C6 C5 118.4(8) . . ?
C7 C6 C5 115.5(8) . . ?
C8 C7 C6 112.9(8) . . ?
C8 C7 Ir1 130.9(7) . . ?
C6 C7 Ir1 116.1(6) . . ?
N3 C8 C7 121.0(9) . . ?
N3 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
N4 C9 N2 119.0(8) . . ?
N4 C9 N3 121.0(8) . . ?
N2 C9 N3 120.0(8) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C12 C13 108.6(9) . . ?
C16 C12 C17 127.3(9) . . ?
C13 C12 C17 124.0(10) . . ?
C16 C12 Ir1 71.4(5) . . ?
C13 C12 Ir1 70.6(5) . . ?
C17 C12 Ir1 124.7(7) . . ?
C14 C13 C12 106.1(9) . . ?
C14 C13 C18 127.2(10) . . ?
C12 C13 C18 125.8(10) . . ?
C14 C13 Ir1 73.9(5) . . ?
C12 C13 Ir1 69.5(5) . . ?
C18 C13 Ir1 129.6(7) . . ?
C15 C14 C13 109.2(9) . . ?
C15 C14 C19 127.1(10) . . ?
C13 C14 C19 123.7(10) . . ?
C15 C14 Ir1 72.6(5) . . ?
C13 C14 Ir1 67.7(5) . . ?
C19 C14 Ir1 126.2(7) . . ?
C14 C15 C16 107.7(9) . . ?
C14 C15 C20 126.6(10) . . ?
C16 C15 C20 125.7(9) . . ?
C14 C15 Ir1 70.4(5) . . ?
C16 C15 Ir1 66.9(5) . . ?
C20 C15 Ir1 129.2(7) . . ?
C12 C16 C15 108.2(9) . . ?
C12 C16 C21 126.4(9) . . ?
C15 C16 C21 125.0(9) . . ?
C12 C16 Ir1 70.1(5) . . ?
C15 C16 Ir1 75.0(5) . . ?
C21 C16 Ir1 127.0(7) . . ?
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 . . ?
C1 N1 C5 118.5(8) . . ?
C1 N1 Ir1 124.3(6) . . ?
C5 N1 Ir1 117.0(6) . . ?
C6 N2 C9 117.6(8) . . ?
C8 N3 C9 122.2(8) . . ?
C8 N3 H3N 118.9 . . ?
C9 N3 H3N 118.9 . . ?
C9 N4 C10 119.7(8) . . ?
C9 N4 C11 120.6(8) . . ?
C10 N4 C11 117.2(8) . . ?
C7 Ir1 N1 77.8(3) . . ?
C7 Ir1 C12 97.6(4) . . ?
N1 Ir1 C12 127.1(3) . . ?
C7 Ir1 C13 108.5(4) . . ?
N1 Ir1 C13 165.1(3) . . ?
C12 Ir1 C13 39.9(4) . . ?
C7 Ir1 C16 120.9(4) . . ?
N1 Ir1 C16 99.2(3) . . ?
C12 Ir1 C16 38.6(4) . . ?
C13 Ir1 C16 65.9(4) . . ?
C7 Ir1 C14 145.1(4) . . ?
N1 Ir1 C14 137.1(3) . . ?
C12 Ir1 C14 64.2(4) . . ?
C13 Ir1 C14 38.4(4) . . ?
C16 Ir1 C14 63.8(4) . . ?
C7 Ir1 C15 158.8(4) . . ?
N1 Ir1 C15 105.2(3) . . ?
C12 Ir1 C15 63.6(4) . . ?
C13 Ir1 C15 64.0(4) . . ?
C16 Ir1 C15 38.1(4) . . ?
C14 Ir1 C15 37.0(4) . . ?
C7 Ir1 Cl1 86.4(3) . . ?
N1 Ir1 Cl1 87.2(2) . . ?
C12 Ir1 Cl1 145.6(3) . . ?
C13 Ir1 Cl1 106.4(3) . . ?
C16 Ir1 Cl1 152.6(3) . . ?
C14 Ir1 Cl1 93.4(3) . . ?
C15 Ir1 Cl1 114.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        62.43
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         4.494
_refine_diff_density_min         -1.563
_refine_diff_density_rms         0.253

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.056 0.500 0.500 262 88 ' '
_platon_squeeze_details          
;
;
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1541498'
_audit_update_record             
;
2017-03-31 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 B Cl F4 Ir N4'
_chemical_formula_weight         621.87

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'
B B 0.0013 0.0007 '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                   8.8142(1)
_cell_length_b                   15.6347(2)
_cell_length_c                   15.1228(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.195(1)
_cell_angle_gamma                90
_cell_volume                     2084.02(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9575
_cell_measurement_theta_min      3.7020
_cell_measurement_theta_max      32.1320

_exptl_crystal_description       'transparent block'
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_F_000             1200
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.224
_exptl_absorpt_coefficient_mu    6.584
_shelx_estimated_absorpt_T_min   0.198
_shelx_estimated_absorpt_T_max   0.320
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.168
_exptl_absorpt_correction_T_max  0.330
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1399
_diffrn_reflns_number            21720
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.933
_diffrn_reflns_theta_max         32.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6873
_reflns_number_gt                6323
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0115P)²+2.6993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6873
_refine_ls_number_parameters     282
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0466
_refine_ls_wR_factor_gt          0.0453
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.003
_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
C1 C -0.0938(3) 0.53150(17) 0.72208(19) 0.0242(5) Uani 1 1 d . . . . .
H1 H -0.0514 0.5566 0.7738 0.029 Uiso 1 1 calc R U . . .
C2 C -0.2354(3) 0.5577(2) 0.6930(2) 0.0305(6) Uani 1 1 d . . . . .
H2 H -0.2904 0.5998 0.7248 0.037 Uiso 1 1 calc R U . . .
C3 C -0.2951(3) 0.5223(2) 0.6178(2) 0.0329(7) Uani 1 1 d . . . . .
H3 H -0.3925 0.5395 0.5974 0.039 Uiso 1 1 calc R U . . .
C4 C -0.2143(3) 0.4618(2) 0.5717(2) 0.0292(6) Uani 1 1 d . . . . .
H4 H -0.2546 0.4374 0.5192 0.035 Uiso 1 1 calc R U . . .
C5 C -0.0717(3) 0.43680(16) 0.60364(17) 0.0200(5) Uani 1 1 d . . . . .
C6 C 0.0313(3) 0.37961(16) 0.55686(16) 0.0198(5) Uani 1 1 d . . . . .
C7 C -0.0019(3) 0.3382(2) 0.47900(19) 0.0299(6) Uani 1 1 d . . . . .
H7 H -0.0980 0.3432 0.4509 0.036 Uiso 1 1 calc R U . . .
C8 C 0.1134(4) 0.2887(2) 0.4441(2) 0.0353(7) Uani 1 1 d . . . . .
H8 H 0.0904 0.2540 0.3943 0.042 Uiso 1 1 calc R U . . .
C9 C 0.2809(3) 0.33391(16) 0.54785(17) 0.0222(5) Uani 1 1 d . . . . .
C10 C 0.2488(3) 0.43675(17) 0.86251(17) 0.0221(5) Uani 1 1 d . . . . .
C11 C 0.1090(3) 0.39083(17) 0.85853(16) 0.0205(5) Uani 1 1 d . . . . .
C12 C 0.1320(3) 0.31319(16) 0.80953(16) 0.0177(4) Uani 1 1 d . . . . .
C13 C 0.2921(3) 0.30804(16) 0.78857(16) 0.0185(5) Uani 1 1 d . . . . .
C14 C 0.3638(3) 0.38460(17) 0.81960(17) 0.0210(5) Uani 1 1 d . . . . .
C15 C 0.2781(4) 0.5193(2) 0.9094(2) 0.0355(7) Uani 1 1 d . . . . .
H15A H 0.1860 0.5544 0.9082 0.053 Uiso 1 1 calc R U . . .
H15B H 0.3606 0.5499 0.8798 0.053 Uiso 1 1 calc R U . . .
H15C H 0.3069 0.5076 0.9709 0.053 Uiso 1 1 calc R U . . .
C16 C -0.0383(3) 0.4161(2) 0.89886(19) 0.0293(6) Uani 1 1 d . . . . .
H16A H -0.0517 0.3857 0.9550 0.044 Uiso 1 1 calc R U . . .
H16B H -0.1214 0.4014 0.8585 0.044 Uiso 1 1 calc R U . . .
H16C H -0.0386 0.4779 0.9097 0.044 Uiso 1 1 calc R U . . .
C17 C 0.0171(3) 0.24531(17) 0.79410(19) 0.0254(5) Uani 1 1 d . . . . .
H17A H 0.0109 0.2084 0.8464 0.038 Uiso 1 1 calc R U . . .
H17B H 0.0466 0.2110 0.7427 0.038 Uiso 1 1 calc R U . . .
H17C H -0.0820 0.2717 0.7830 0.038 Uiso 1 1 calc R U . . .
C18 C 0.3656(3) 0.23264(17) 0.74543(19) 0.0255(5) Uani 1 1 d . . . . .
H18A H 0.4702 0.2471 0.7297 0.038 Uiso 1 1 calc R U . . .
H18B H 0.3089 0.2173 0.6919 0.038 Uiso 1 1 calc R U . . .
H18C H 0.3657 0.1841 0.7865 0.038 Uiso 1 1 calc R U . . .
C19 C 0.5276(3) 0.4076(2) 0.8150(2) 0.0322(7) Uani 1 1 d . . . . .
H19A H 0.5738 0.4015 0.8737 0.048 Uiso 1 1 calc R U . . .
H19B H 0.5379 0.4669 0.7949 0.048 Uiso 1 1 calc R U . . .
H19C H 0.5790 0.3694 0.7732 0.048 Uiso 1 1 calc R U . . .
N1 N -0.0146(2) 0.47082(13) 0.67836(14) 0.0188(4) Uani 1 1 d . . . . .
N2 N 0.1708(2) 0.37334(13) 0.59519(13) 0.0180(4) Uani 1 1 d . . . . .
N3 N 0.2530(3) 0.28656(16) 0.47534(16) 0.0309(5) Uani 1 1 d . . . . .
N4 N 0.4239(3) 0.34289(17) 0.57340(17) 0.0283(5) Uani 1 1 d D . . . .
H4A H 0.494(3) 0.3103(19) 0.548(2) 0.034 Uiso 1 1 d D U . . .
H4B H 0.442(4) 0.3774(19) 0.6187(18) 0.034 Uiso 1 1 d D U . . .
F1 F 0.6797(2) 0.24343(12) 0.50920(12) 0.0351(4) Uani 1 1 d . . . . .
F2 F 0.6137(3) 0.13383(16) 0.59761(16) 0.0654(7) Uani 1 1 d . . . . .
F3 F 0.7295(3) 0.24868(17) 0.65523(14) 0.0574(6) Uani 1 1 d . . . . .
F4 F 0.8623(3) 0.15884(19) 0.5675(2) 0.0818(9) Uani 1 1 d . . . . .
Cl1 Cl 0.31352(7) 0.54132(4) 0.66298(4) 0.02239(12) Uani 1 1 d . . . . .
Ir1 Ir 0.18806(2) 0.41919(2) 0.72529(2) 0.01452(3) Uani 1 1 d . . . . .
B1 B 0.7240(4) 0.1951(2) 0.5827(3) 0.0346(8) 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 N1 1.352(3) . ?
C1 C2 1.384(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(4) . ?
C4 H4 0.9500 . ?
C5 N1 1.345(3) . ?
C5 C6 1.459(4) . ?
C6 N2 1.361(3) . ?
C6 C7 1.375(4) . ?
C7 C8 1.383(5) . ?
C7 H7 0.9500 . ?
C8 N3 1.316(4) . ?
C8 H8 0.9500 . ?
C9 N4 1.325(4) . ?
C9 N3 1.345(3) . ?
C9 N2 1.356(3) . ?
C10 C11 1.427(4) . ?
C10 C14 1.455(4) . ?
C10 C15 1.494(4) . ?
C10 Ir1 2.159(3) . ?
C11 C12 1.437(4) . ?
C11 C16 1.490(4) . ?
C11 Ir1 2.180(2) . ?
C12 C13 1.450(3) . ?
C12 C17 1.485(3) . ?
C12 Ir1 2.149(2) . ?
C13 C14 1.432(4) . ?
C13 C18 1.496(4) . ?
C13 Ir1 2.184(2) . ?
C14 C19 1.490(4) . ?
C14 Ir1 2.170(2) . ?
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 . ?
N1 Ir1 2.083(2) . ?
N2 Ir1 2.099(2) . ?
N4 H4A 0.889(18) . ?
N4 H4B 0.887(18) . ?
F1 B1 1.398(4) . ?
F2 B1 1.384(4) . ?
F3 B1 1.381(4) . ?
F4 B1 1.364(4) . ?
Cl1 Ir1 2.4008(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.2(3) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 118.9(3) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 120.8(3) . . ?
N1 C5 C6 114.7(2) . . ?
C4 C5 C6 124.3(2) . . ?
N2 C6 C7 121.4(3) . . ?
N2 C6 C5 113.6(2) . . ?
C7 C6 C5 125.0(2) . . ?
C6 C7 C8 115.8(3) . . ?
C6 C7 H7 122.1 . . ?
C8 C7 H7 122.1 . . ?
N3 C8 C7 124.4(3) . . ?
N3 C8 H8 117.8 . . ?
C7 C8 H8 117.8 . . ?
N4 C9 N3 117.9(3) . . ?
N4 C9 N2 118.7(2) . . ?
N3 C9 N2 123.4(3) . . ?
C11 C10 C14 107.6(2) . . ?
C11 C10 C15 127.0(3) . . ?
C14 C10 C15 125.2(3) . . ?
C11 C10 Ir1 71.59(14) . . ?
C14 C10 Ir1 70.79(14) . . ?
C15 C10 Ir1 127.4(2) . . ?
C10 C11 C12 108.9(2) . . ?
C10 C11 C16 127.1(2) . . ?
C12 C11 C16 124.0(2) . . ?
C10 C11 Ir1 70.00(14) . . ?
C12 C11 Ir1 69.46(14) . . ?
C16 C11 Ir1 127.30(18) . . ?
C11 C12 C13 107.4(2) . . ?
C11 C12 C17 126.0(2) . . ?
C13 C12 C17 126.1(2) . . ?
C11 C12 Ir1 71.77(14) . . ?
C13 C12 Ir1 71.77(14) . . ?
C17 C12 Ir1 128.04(18) . . ?
C14 C13 C12 108.1(2) . . ?
C14 C13 C18 127.6(2) . . ?
C12 C13 C18 124.2(2) . . ?
C14 C13 Ir1 70.28(14) . . ?
C12 C13 Ir1 69.15(13) . . ?
C18 C13 Ir1 128.14(17) . . ?
C13 C14 C10 107.9(2) . . ?
C13 C14 C19 127.8(3) . . ?
C10 C14 C19 124.2(3) . . ?
C13 C14 Ir1 71.32(14) . . ?
C10 C14 Ir1 69.94(14) . . ?
C19 C14 Ir1 126.77(19) . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 . . ?
C5 N1 C1 119.8(2) . . ?
C5 N1 Ir1 116.80(17) . . ?
C1 N1 Ir1 123.30(18) . . ?
C9 N2 C6 117.1(2) . . ?
C9 N2 Ir1 126.89(17) . . ?
C6 N2 Ir1 115.93(16) . . ?
C8 N3 C9 116.5(3) . . ?
C9 N4 H4A 119(2) . . ?
C9 N4 H4B 117(2) . . ?
H4A N4 H4B 124(3) . . ?
N1 Ir1 N2 75.73(8) . . ?
N1 Ir1 C12 107.58(9) . . ?
N2 Ir1 C12 106.03(9) . . ?
N1 Ir1 C10 119.21(9) . . ?
N2 Ir1 C10 164.01(9) . . ?
C12 Ir1 C10 65.49(10) . . ?
N1 Ir1 C14 158.41(10) . . ?
N2 Ir1 C14 125.46(9) . . ?
C12 Ir1 C14 65.38(9) . . ?
C10 Ir1 C14 39.27(10) . . ?
N1 Ir1 C11 96.74(9) . . ?
N2 Ir1 C11 140.77(9) . . ?
C12 Ir1 C11 38.76(9) . . ?
C10 Ir1 C11 38.41(10) . . ?
C14 Ir1 C11 64.63(10) . . ?
N1 Ir1 C13 144.68(9) . . ?
N2 Ir1 C13 99.67(9) . . ?
C12 Ir1 C13 39.08(9) . . ?
C10 Ir1 C13 65.01(10) . . ?
C14 Ir1 C13 38.39(9) . . ?
C11 Ir1 C13 64.41(9) . . ?
N1 Ir1 Cl1 87.35(6) . . ?
N2 Ir1 Cl1 86.32(6) . . ?
C12 Ir1 Cl1 162.41(7) . . ?
C10 Ir1 Cl1 99.38(7) . . ?
C14 Ir1 Cl1 97.32(7) . . ?
C11 Ir1 Cl1 132.35(7) . . ?
C13 Ir1 Cl1 127.70(7) . . ?
F4 B1 F3 110.9(3) . . ?
F4 B1 F2 111.6(3) . . ?
F3 B1 F2 108.2(3) . . ?
F4 B1 F1 109.8(3) . . ?
F3 B1 F1 108.2(3) . . ?
F2 B1 F1 108.0(3) . . ?

_refine_diff_density_max         0.716
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.106

