# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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 1497501'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_audit_creation_date             2016-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            'Ir(pyalk)2Cl2, "purple isomer"'
_chemical_name_systematic        
'trans-Cl, trans-O, trans-N-bis(2-{pyridin-2-yl}propan-2-olato)-dichloro-iridium(IV)'
_chemical_formula_moiety         'C16 H20 Cl2 Ir N2 O2'
_chemical_formula_sum            'C16 H20 Cl2 Ir N2 O2'
_chemical_formula_weight         535.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.87680(10)
_cell_length_b                   8.08110(10)
_cell_length_c                   8.6738(6)
_cell_angle_alpha                68.100(5)
_cell_angle_beta                 66.086(5)
_cell_angle_gamma                61.433(4)
_cell_volume                     432.10(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    15210
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.3
_cell_measurement_theta_min      5.7
_shelx_estimated_absorpt_T_max   0.468
_shelx_estimated_absorpt_T_min   0.468
_exptl_absorpt_coefficient_mu    17.886
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Dark purple'
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.058
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             257
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1142
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15649
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.234
_diffrn_reflns_theta_min         5.724
_diffrn_ambient_temperature      93
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 0.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 0.0000
	             Phi: 180.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 220.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 50.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 125.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 55.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 225.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 300.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 250.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 320.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 110.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 150.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 75.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 350.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 0.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 275.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 25.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 175.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 0.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 325.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: -48.0000 - 132.0000
	     Image width: 2.0000
	        Exp time: 2.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 165.0000
	             XTD: 42.3084
	          2theta: 40.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 275.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 100.0000
	             XTD: 42.3084
	          2theta: 88.5749
scan:
	Number of images: 90
	           Slice: 0.0000 - 180.0000
	     Image width: 2.0000
	        Exp time: 6.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	           Kappa: 54.0000
	             Phi: 200.0000
	             XTD: 42.3084
	          2theta: 88.5749
;
_diffrn_measurement_device       
;
AFC11 (Left): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn944+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Unknown
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      0.138790
_diffrn_orient_matrix_UB_12      -0.058202
_diffrn_orient_matrix_UB_13      -0.075081
_diffrn_orient_matrix_UB_21      -0.021016
_diffrn_orient_matrix_UB_22      -0.121376
_diffrn_orient_matrix_UB_23      0.026091
_diffrn_orient_matrix_UB_31      -0.054307
_diffrn_orient_matrix_UB_32      0.052661
_diffrn_orient_matrix_UB_33      -0.102083
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1549
_reflns_number_total             1549
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.411
_refine_diff_density_min         -2.036
_refine_diff_density_rms         0.239
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0446P)²+1.1622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0820
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.018) H8A(0.034) H8B(0.034) H8C(0.034) H4(0.019) H2(0.022)
 H7A(0.032) H7B(0.032) H7C(0.032)
 Fixed X: Ir1(1) H1(0.638) H8A(0.8915) H8B(0.6963) H8C(0.9045) H4(0.4043)
 H2(0.3156) H7A(0.7978) H7B(0.5774) H7C(0.6917)
 Fixed Y: Ir1(0) H1(-0.1139) H8A(0.1837) H8B(0.3721) H8C(0.387) H4(0.3681) H2(-
 0.0247) H7A(0.5795) H7B(0.5908) H7C(0.513)
 Fixed Z: Ir1(0.5) H1(0.616) H8A(0.8976) H8B(0.9196) H8C(0.8077) H4(0.897)
 H2(0.7938) H7A(0.5414) H7B(0.6406) H7C(0.4705)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 1.0000 0.0000 0.5000 0.00894(15) Uani 1 2 d S T P . .
Cl1 Cl 0.8912(2) 0.2187(2) 0.25789(18) 0.0165(3) Uani 1 1 d . . . . .
O1 O 0.9799(6) 0.2089(6) 0.5748(5) 0.0145(9) Uani 1 1 d . . . . .
N1 N 0.7099(7) 0.0717(7) 0.6488(6) 0.0129(10) Uani 1 1 d . . . . .
C1 C 0.5895(9) -0.0162(9) 0.6731(8) 0.0152(12) Uani 1 1 d . . . . .
H1 H 0.6380 -0.1139 0.6160 0.018 Uiso 1 1 calc R . . . .
C8 C 0.8235(10) 0.3139(11) 0.8414(9) 0.0225(15) Uani 1 1 d . . . . .
H8A H 0.8915 0.1837 0.8976 0.034 Uiso 1 1 calc GR . . . .
H8B H 0.6963 0.3721 0.9196 0.034 Uiso 1 1 calc GR . . . .
H8C H 0.9045 0.3870 0.8077 0.034 Uiso 1 1 calc GR . . . .
C6 C 0.7887(9) 0.3124(8) 0.6798(8) 0.0138(12) Uani 1 1 d . . . . .
C5 C 0.6431(9) 0.2155(8) 0.7281(8) 0.0135(12) Uani 1 1 d . . . . .
C4 C 0.4499(9) 0.2706(9) 0.8406(8) 0.0159(13) Uani 1 1 d . . . . .
H4 H 0.4043 0.3681 0.8970 0.019 Uiso 1 1 calc R . . . .
C3 C 0.3269(9) 0.1804(9) 0.8679(8) 0.0165(13) Uani 1 1 d . . . . .
C2 C 0.3980(9) 0.0354(9) 0.7797(8) 0.0183(13) Uani 1 1 d . . . . .
H2 H 0.3156 -0.0247 0.7938 0.022 Uiso 1 1 calc R . . . .
C7 C 0.7062(10) 0.5181(9) 0.5731(9) 0.0212(14) Uani 1 1 d . . . . .
H7A H 0.7978 0.5795 0.5414 0.032 Uiso 1 1 calc GR . . . .
H7B H 0.5774 0.5908 0.6406 0.032 Uiso 1 1 calc GR . . . .
H7C H 0.6917 0.5130 0.4705 0.032 Uiso 1 1 calc GR . . . .
H3 H 0.194(11) 0.215(9) 0.947(9) 0.010(16) 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
Ir1 Cl1 2.3473(15) 2_756 ?
Ir1 Cl1 2.3473(15) . ?
Ir1 O1 1.943(4) . ?
Ir1 O1 1.943(4) 2_756 ?
Ir1 N1 2.031(5) . ?
Ir1 N1 2.031(5) 2_756 ?
O1 C6 1.432(7) . ?
N1 C1 1.349(8) . ?
N1 C5 1.348(8) . ?
C1 C2 1.364(9) . ?
C8 C6 1.538(9) . ?
C6 C5 1.526(8) . ?
C6 C7 1.533(9) . ?
C5 C4 1.392(9) . ?
C4 C3 1.373(9) . ?
C3 C2 1.402(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
Cl1 Ir1 Cl1 180.0 . 2_756 ?
O1 Ir1 Cl1 90.68(13) 2_756 2_756 ?
O1 Ir1 Cl1 90.68(13) . . ?
O1 Ir1 Cl1 89.32(13) . 2_756 ?
O1 Ir1 Cl1 89.32(13) 2_756 . ?
O1 Ir1 O1 180.0(2) . 2_756 ?
O1 Ir1 N1 98.14(18) 2_756 . ?
O1 Ir1 N1 98.14(18) . 2_756 ?
O1 Ir1 N1 81.86(18) . . ?
O1 Ir1 N1 81.86(18) 2_756 2_756 ?
N1 Ir1 Cl1 90.05(14) 2_756 2_756 ?
N1 Ir1 Cl1 90.05(14) . . ?
N1 Ir1 Cl1 89.95(14) . 2_756 ?
N1 Ir1 Cl1 89.95(14) 2_756 . ?
N1 Ir1 N1 180.0 . 2_756 ?
C6 O1 Ir1 117.5(3) . . ?
C1 N1 Ir1 124.5(4) . . ?
C5 N1 Ir1 114.7(4) . . ?
C5 N1 C1 120.7(5) . . ?
N1 C1 C2 121.3(6) . . ?
O1 C6 C8 107.5(5) . . ?
O1 C6 C5 109.9(5) . . ?
O1 C6 C7 107.8(5) . . ?
C5 C6 C8 111.5(5) . . ?
C5 C6 C7 109.1(5) . . ?
C7 C6 C8 111.1(5) . . ?
N1 C5 C6 115.5(5) . . ?
N1 C5 C4 119.9(5) . . ?
C4 C5 C6 124.5(5) . . ?
C3 C4 C5 119.8(6) . . ?
C4 C3 C2 119.1(6) . . ?
C1 C2 C3 119.1(6) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_14022
_database_code_depnum_ccdc_archive 'CCDC 1497502'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         '16(C16 H20 Cl2 Ir N2 O2)'
_chemical_formula_sum            'C256 H320 Cl32 Ir16 N32 O32'
_chemical_formula_weight         8567.53
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69945 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Ir -4.39616 6.81637 27.30490 16.72960 15.61150 5.83377 1.59279 8.86553 0.41792
45.00110 11.4722003937
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03257 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/4,x+3/4,z+3/4
3 y+1/4,-x+1/4,z+1/4
4 -x,-y+1/2,z
5 -x,-y,-z
6 y-1/4,-x-3/4,-z-3/4
7 -y-1/4,x-1/4,-z-1/4
8 x,y-1/2,-z
9 x+1/2,y+1/2,z+1/2
10 -y+3/4,x+5/4,z+5/4
11 y+3/4,-x+3/4,z+3/4
12 -x+1/2,-y+1,z+1/2
13 -x+1/2,-y+1/2,-z+1/2
14 y+1/4,-x-1/4,-z-1/4
15 -y+1/4,x+1/4,-z+1/4
16 x+1/2,y,-z+1/2

_symmetry_Int_Tables_number      88
_cell_length_a                   16.9129(3)
_cell_length_b                   16.9129(3)
_cell_length_c                   25.3688(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7256.6(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    30619
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      3.1
_exptl_absorpt_coefficient_mu    17.041
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   Multi-scan
_exptl_crystal_colour            'Dark maroon'
_exptl_crystal_density_diffrn    1.9604
_exptl_crystal_description       Block
_exptl_crystal_F_000             4062.1851
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0729
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            96480
_diffrn_reflns_theta_full        68.2368
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         3.14
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 22.2222
_diffrn_measured_fraction_theta_full 0.9994
_diffrn_measured_fraction_theta_max 0.9994
_diffrn_measurement_device       
;
AFC11 (Left): Eulerian 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn944+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              20
_reflns_limit_h_min              0
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                3243
_reflns_number_total             3317
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.7449
_refine_diff_density_min         -0.6349
_refine_diff_density_rms         0.1206
_refine_ls_d_res_high            0.8301
_refine_ls_d_res_low             14.0723
_refine_ls_goodness_of_fit_ref   1.0360
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3317
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0234
_refine_ls_restrained_S_all      1.0360
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0126P)²+71.7760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0516
_refine_ls_wR_factor_ref         0.0519
_olex2_refinement_description    
;
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Ir1 Ir 0.245652(9) 0.536773(9) 0.009073(6) 0.01463(6) Uani 1.000000 .
Cl1 Cl 0.14166(5) 0.62720(5) 0.00296(4) 0.02193(19) Uani 1.000000 .
Cl2 Cl 0.34680(5) 0.44985(5) 0.03038(4) 0.02168(19) Uani 1.000000 .
O1 O 0.21335(15) 0.47700(15) -0.05240(10) 0.0196(5) Uani 1.000000 .
N2 N 0.29205(18) 0.61579(18) 0.06392(12) 0.0175(6) Uani 1.000000 .
O2 O 0.31379(15) 0.59827(15) -0.03798(10) 0.0192(5) Uani 1.000000 .
N1 N 0.16467(17) 0.46084(17) 0.04475(12) 0.0159(6) Uani 1.000000 .
C13 C 0.3382(2) 0.6726(2) 0.04166(14) 0.0157(7) Uani 1.000000 .
C5 C 0.1260(2) 0.4149(2) 0.00984(15) 0.0177(7) Uani 1.000000 .
C12 C 0.3642(2) 0.7358(2) 0.07118(15) 0.0205(8) Uani 1.000000 .
H12 H 0.3946(2) 0.7750(2) 0.05546(15) 0.0246(9) Uiso 1.000000 R
C14 C 0.3594(2) 0.6605(2) -0.01615(14) 0.0178(7) Uani 1.000000 .
C3 C 0.0452(2) 0.3624(2) 0.07874(16) 0.0230(8) Uani 1.000000 .
H3 H 0.0038(2) 0.3304(2) 0.08994(16) 0.0276(10) Uiso 1.000000 R
C1 C 0.1459(2) 0.4565(2) 0.09662(15) 0.0238(8) Uani 1.000000 .
H1 H 0.1740(2) 0.4871(2) 0.12073(15) 0.0285(10) Uiso 1.000000 R
C10 C 0.3015(2) 0.6818(2) 0.14681(15) 0.0239(8) Uani 1.000000 .
H10 H 0.2896(2) 0.6835(2) 0.18258(15) 0.0287(10) Uiso 1.000000 R
C6 C 0.1499(2) 0.4218(2) -0.04725(15) 0.0187(8) Uani 1.000000 .
C16 C 0.4468(2) 0.6366(3) -0.01958(16) 0.0264(9) Uani 1.000000 .
H16a H 0.4548(4) 0.5881(10) -0.0007(10) 0.0395(13) Uiso 1.000000 GR
H16b H 0.4612(5) 0.6293(17) -0.05585(18) 0.0395(13) Uiso 1.000000 GR
H16c H 0.4789(3) 0.6775(8) -0.0044(11) 0.0395(13) Uiso 1.000000 GR
C4 C 0.0663(2) 0.3647(2) 0.02635(16) 0.0219(8) Uani 1.000000 .
H4 H 0.0404(2) 0.3326(2) 0.00209(16) 0.0263(10) Uiso 1.000000 R
C9 C 0.2756(2) 0.6201(2) 0.11599(15) 0.0211(8) Uani 1.000000 .
H9 H 0.2459(2) 0.5800(2) 0.13146(15) 0.0253(10) Uiso 1.000000 R
C2 C 0.0864(2) 0.4080(2) 0.11435(16) 0.0254(9) Uani 1.000000 .
H2 H 0.0740(2) 0.4060(2) 0.15005(16) 0.0305(10) Uiso 1.000000 R
C8 C 0.0809(3) 0.4529(3) -0.07987(17) 0.0319(10) Uani 1.000000 .
H8a H 0.0645(13) 0.5033(9) -0.0663(8) 0.0478(15) Uiso 1.000000 GR
H8b H 0.0972(6) 0.4587(18) -0.1159(3) 0.0478(15) Uiso 1.000000 GR
H8c H 0.0376(7) 0.4164(10) -0.0779(10) 0.0478(15) Uiso 1.000000 GR
C15 C 0.3424(3) 0.7344(2) -0.04845(17) 0.0308(10) Uani 1.000000 .
H15a H 0.3510(18) 0.7234(6) -0.0851(2) 0.0462(15) Uiso 1.000000 GR
H15b H 0.2884(6) 0.7502(11) -0.0432(10) 0.0462(15) Uiso 1.000000 GR
H15c H 0.3770(13) 0.7762(6) -0.0374(9) 0.0462(15) Uiso 1.000000 GR
C11 C 0.3453(2) 0.7411(2) 0.12383(16) 0.0239(8) Uani 1.000000 .
H11 H 0.3620(2) 0.7843(2) 0.14364(16) 0.0286(10) Uiso 1.000000 R
C7 C 0.1791(3) 0.3428(2) -0.06806(18) 0.0339(11) Uani 1.000000 .
H7a H 0.1964(19) 0.3489(5) -0.1039(5) 0.0508(16) Uiso 1.000000 GR
H7b H 0.2225(13) 0.3247(10) -0.0468(8) 0.0508(16) Uiso 1.000000 GR
H7c H 0.1370(6) 0.3048(6) -0.0667(12) 0.0508(16) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 Cl1 2.3358(9) . ?
Ir1 Cl2 2.3195(9) . ?
Ir1 O1 1.937(3) . ?
Ir1 N2 2.083(3) . ?
Ir1 O2 1.958(2) . ?
Ir1 N1 2.084(3) . ?
O1 C6 1.429(4) . ?
N2 C13 1.361(5) . ?
N2 C9 1.352(5) . ?
O2 C14 1.417(4) . ?
N1 C5 1.348(5) . ?
N1 C1 1.355(5) . ?
C13 C12 1.376(5) . ?
C13 C14 1.524(5) . ?
C5 C6 1.508(5) . ?
C5 C4 1.384(5) . ?
C12 C11 1.376(6) . ?
C14 C16 1.534(5) . ?
C14 C15 1.523(5) . ?
C3 C4 1.376(6) . ?
C3 C2 1.377(6) . ?
C1 C2 1.375(6) . ?
C10 C9 1.377(5) . ?
C10 C11 1.376(6) . ?
C6 C8 1.524(5) . ?
C6 C7 1.520(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
Cl2 Ir1 Cl1 170.32(3) . . ?
O1 Ir1 Cl1 94.35(8) . . ?
O1 Ir1 Cl2 93.72(8) . . ?
N2 Ir1 Cl1 84.72(9) . . ?
N2 Ir1 Cl2 88.46(9) . . ?
N2 Ir1 O1 168.22(11) . . ?
O2 Ir1 Cl1 93.15(8) . . ?
O2 Ir1 Cl2 92.56(8) . . ?
O2 Ir1 O1 87.27(10) . . ?
O2 Ir1 N2 81.07(11) . . ?
N1 Ir1 Cl1 86.41(8) . . ?
N1 Ir1 Cl2 89.60(8) . . ?
N1 Ir1 O1 80.95(11) . . ?
N1 Ir1 N2 110.66(12) . . ?
N1 Ir1 O2 168.14(11) . . ?
C6 O1 Ir1 118.6(2) . . ?
C13 N2 Ir1 113.1(2) . . ?
C9 N2 Ir1 127.6(3) . . ?
C9 N2 C13 119.1(3) . . ?
C14 O2 Ir1 118.5(2) . . ?
C5 N1 Ir1 112.9(2) . . ?
C1 N1 Ir1 127.5(3) . . ?
C1 N1 C5 119.6(3) . . ?
C12 C13 N2 120.3(3) . . ?
C14 C13 N2 116.0(3) . . ?
C14 C13 C12 123.6(3) . . ?
C6 C5 N1 117.1(3) . . ?
C4 C5 N1 120.6(3) . . ?
C4 C5 C6 122.3(3) . . ?
C11 C12 C13 120.4(4) . . ?
C13 C14 O2 110.4(3) . . ?
C16 C14 O2 107.9(3) . . ?
C16 C14 C13 108.5(3) . . ?
C15 C14 O2 107.2(3) . . ?
C15 C14 C13 111.3(3) . . ?
C15 C14 C16 111.6(3) . . ?
C2 C3 C4 119.1(4) . . ?
C2 C1 N1 121.4(4) . . ?
C11 C10 C9 118.9(4) . . ?
C5 C6 O1 109.9(3) . . ?
C8 C6 O1 107.4(3) . . ?
C8 C6 C5 110.1(3) . . ?
C7 C6 O1 107.3(3) . . ?
C7 C6 C5 110.6(3) . . ?
C7 C6 C8 111.4(4) . . ?
C3 C4 C5 119.9(4) . . ?
C10 C9 N2 122.0(4) . . ?
C1 C2 C3 119.4(4) . . ?
C10 C11 C12 119.2(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        
'trans-Cl, cis-O, cis-N-bis(2-{pyridin-2-yl}propan-2-olato)-dichloro-iridium(IV)'
_chemical_name_common            'Ir(pyalk)2Cl2, "maroon isomer"'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane. pentane'
_chemical_properties_physical    
', Heat-sensitive,Oxidizer: reduction-sensitive; converts to other isomers on heating'
####################################################################### 
# 
# 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_6iii
_database_code_depnum_ccdc_archive 'CCDC 1497503'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_PLAT928_6iii                
;
PROBLEM: Reported and Calculated    S value   Differ by .      0.245     .      
RESPONSE: CIF and FCF both originate from the last SHELXL cycle.
This may be a false alert derived from the number of outlier
reflections that were rejected.
 
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Hydrogen cis-Cl, cis-O, cis-N-bis(2-{pyridin-2-yl}propan-2-olato)-dichloro-iridate(III)'
_chemical_name_common            'Ir(pyalk)(Hpyalk)Cl2, red isomer'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H21 Cl2 Ir N2 O2, H2 O'
_chemical_formula_sum            'C16 H23 Cl2 Ir N2 O3'
_chemical_formula_weight         554.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.8884(3)
_cell_length_b                   9.6675(3)
_cell_length_c                   12.5862(9)
_cell_angle_alpha                95.132(7)
_cell_angle_beta                 109.482(8)
_cell_angle_gamma                110.349(8)
_cell_volume                     929.79(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    16196
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      30.5

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    7.484
_shelx_estimated_absorpt_T_min   0.522
_shelx_estimated_absorpt_T_max   0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.854
_diffrn_ambient_temperature      93(2)
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'


_exptl_special_details           
; 
 'Rigaku R-AXIS RAPID, Rigaku R-AXIS RAPID imaging plate' 
;

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            16078
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.217
_diffrn_reflns_theta_max         25.028
_diffrn_reflns_theta_full        25.028
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3227
_reflns_number_gt                3115
_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       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0541P)²+5.9230P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3225
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0171
_refine_ls_wR_factor_ref         0.0452
_refine_ls_wR_factor_gt          0.0444
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_restrained_S_all      0.881
_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
Ir1 Ir -0.00623(2) 0.91235(2) 0.74680(2) 0.01448(6) Uani 1 1 d . . . . .
N1 N -0.1433(4) 0.7330(3) 0.6124(3) 0.0197(6) Uani 1 1 d . . . . .
N2 N 0.2230(4) 0.9783(3) 0.7282(3) 0.0166(6) Uani 1 1 d . . . . .
O1 O 0.1548(3) 1.0758(3) 0.8995(2) 0.0193(5) Uani 1 1 d . . . . .
O2 O 0.0496(3) 0.7575(3) 0.8295(2) 0.0201(5) Uani 1 1 d . . . . .
C1 C -0.1462(5) 0.6001(4) 0.6379(3) 0.0226(8) Uani 1 1 d . . . . .
C2 C -0.2451(6) 0.4659(5) 0.5523(4) 0.0321(10) Uani 1 1 d . . . . .
H2 H -0.2449 0.3724 0.5700 0.039 Uiso 1 1 calc R U . . .
C3 C -0.3429(6) 0.4682(5) 0.4424(4) 0.0347(10) Uani 1 1 d . . . . .
H3 H -0.4121 0.3767 0.3842 0.042 Uiso 1 1 calc R U . . .
C4 C -0.3395(5) 0.6054(5) 0.4176(4) 0.0322(10) Uani 1 1 d . . . . .
H4 H -0.4060 0.6096 0.3421 0.039 Uiso 1 1 calc R U . . .
C6 C -0.0368(6) 0.6053(4) 0.7610(4) 0.0284(9) Uani 1 1 d . . . . .
C7 C -0.1530(8) 0.5089(5) 0.8155(4) 0.0565(16) Uani 1 1 d . . . . .
H7A H -0.0841 0.5217 0.8975 0.085 Uiso 1 1 calc R U . . .
H7B H -0.2013 0.4020 0.7755 0.085 Uiso 1 1 calc R U . . .
H7C H -0.2484 0.5411 0.8084 0.085 Uiso 1 1 calc R U . . .
C8 C 0.1058(7) 0.5499(6) 0.7594(5) 0.0547(16) Uani 1 1 d . . . . .
H8A H 0.1877 0.6224 0.7343 0.082 Uiso 1 1 calc R U . . .
H8B H 0.0518 0.4504 0.7055 0.082 Uiso 1 1 calc R U . . .
H8C H 0.1684 0.5415 0.8374 0.082 Uiso 1 1 calc R U . . .
C9 C 0.3585(5) 1.0951(4) 0.8097(3) 0.0190(7) Uani 1 1 d . . . . .
C10 C 0.5211(5) 1.1479(4) 0.8032(3) 0.0239(8) Uani 1 1 d . . . . .
H10 H 0.6158 1.2307 0.8616 0.029 Uiso 1 1 calc R U . . .
C11 C 0.5462(5) 1.0816(4) 0.7135(4) 0.0250(8) Uani 1 1 d . . . . .
H11 H 0.6577 1.1164 0.7094 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4054(5) 0.9629(4) 0.6289(3) 0.0237(8) Uani 1 1 d . . . . .
H12 H 0.4182 0.9157 0.5648 0.028 Uiso 1 1 calc R U . . .
C13 C 0.2471(5) 0.9141(4) 0.6385(3) 0.0216(8) Uani 1 1 d . . . . .
H13 H 0.1509 0.8323 0.5801 0.026 Uiso 1 1 calc R U . . .
C14 C 0.3277(5) 1.1711(4) 0.9070(3) 0.0223(8) Uani 1 1 d . . . . .
C15 C 0.4584(5) 1.1812(6) 1.0249(4) 0.0393(11) Uani 1 1 d . . . . .
H15A H 0.4425 1.2386 1.0855 0.059 Uiso 1 1 calc R U . . .
H15B H 0.5770 1.2327 1.0284 0.059 Uiso 1 1 calc R U . . .
H15C H 0.4402 1.0788 1.0369 0.059 Uiso 1 1 calc R U . . .
C16 C 0.3315(6) 1.3257(4) 0.8887(4) 0.0353(10) Uani 1 1 d . . . . .
H16A H 0.2483 1.3138 0.8107 0.053 Uiso 1 1 calc R U . . .
H16B H 0.4490 1.3922 0.8975 0.053 Uiso 1 1 calc R U . . .
H16C H 0.2994 1.3705 0.9462 0.053 Uiso 1 1 calc R U . . .
Cl1 Cl -0.26028(11) 0.84780(10) 0.78524(8) 0.02322(19) Uani 1 1 d . . . . .
Cl2 Cl -0.06890(12) 1.09810(10) 0.64988(8) 0.02392(19) Uani 1 1 d . . . . .
O3 O -0.0421(3) 1.1807(3) 0.9563(2) 0.0255(6) Uani 1 1 d . . . . .
C5 C -0.2388(5) 0.7352(5) 0.5036(3) 0.0264(9) Uani 1 1 d . . . . .
H5 H -0.2357 0.8297 0.4865 0.032 Uiso 1 1 calc R U . . .
H1 H 0.1296 1.1244 0.9453 0.032 Uiso 0.6349 1 d . U P A 1
H3A H 0.0159 1.2377 1.0248 0.032 Uiso 0.6349 1 d . U P A 1
H3B H -0.0517 1.1798 1.0211 0.032 Uiso 0.6349 1 d . U P A 1
H1B H 0.0574 0.7997 0.8943 0.032 Uiso 0.3651 1 d . U P A 2
H3C H 0.0385 1.1483 0.9707 0.032 Uiso 0.3651 1 d . U P A 2
H3D H -0.1343 1.1076 0.9127 0.032 Uiso 0.3651 1 d . U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N1 1.996(3) . ?
Ir1 O2 2.006(2) . ?
Ir1 N2 2.014(3) . ?
Ir1 O1 2.071(2) . ?
Ir1 Cl1 2.3505(9) . ?
Ir1 Cl2 2.3785(9) . ?
N1 C1 1.346(5) . ?
N1 C5 1.356(5) . ?
N2 C9 1.342(5) . ?
N2 C13 1.354(5) . ?
O1 C14 1.457(4) . ?
O1 H1 0.8449 . ?
O2 C6 1.429(4) . ?
O2 H1B 0.8478 . ?
C1 C2 1.393(5) . ?
C1 C6 1.515(6) . ?
C2 C3 1.373(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.371(6) . ?
C4 H4 0.9500 . ?
C6 C7 1.524(6) . ?
C6 C8 1.543(6) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.390(5) . ?
C9 C14 1.521(5) . ?
C10 C11 1.368(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.519(6) . ?
C14 C16 1.523(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
O3 H3A 0.8567 . ?
O3 H3B 0.8488 . ?
O3 H3C 0.8509 . ?
O3 H3D 0.8369 . ?
C5 H5 0.9500 . ?

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 Ir1 O2 82.34(11) . . ?
N1 Ir1 N2 98.26(12) . . ?
O2 Ir1 N2 89.95(11) . . ?
N1 Ir1 O1 170.51(11) . . ?
O2 Ir1 O1 88.44(10) . . ?
N2 Ir1 O1 79.43(11) . . ?
N1 Ir1 Cl1 86.44(9) . . ?
O2 Ir1 Cl1 89.07(8) . . ?
N2 Ir1 Cl1 175.03(9) . . ?
O1 Ir1 Cl1 95.67(7) . . ?
N1 Ir1 Cl2 98.17(9) . . ?
O2 Ir1 Cl2 179.32(8) . . ?
N2 Ir1 Cl2 89.53(9) . . ?
O1 Ir1 Cl2 91.04(7) . . ?
Cl1 Ir1 Cl2 91.42(3) . . ?
C1 N1 C5 119.7(3) . . ?
C1 N1 Ir1 114.9(3) . . ?
C5 N1 Ir1 125.3(3) . . ?
C9 N2 C13 118.8(3) . . ?
C9 N2 Ir1 117.0(2) . . ?
C13 N2 Ir1 124.2(2) . . ?
C14 O1 Ir1 116.2(2) . . ?
C14 O1 H1 107.8 . . ?
Ir1 O1 H1 130.0 . . ?
C6 O2 Ir1 114.9(2) . . ?
C6 O2 H1B 134.2 . . ?
Ir1 O2 H1B 95.1 . . ?
N1 C1 C2 120.0(4) . . ?
N1 C1 C6 117.0(3) . . ?
C2 C1 C6 122.9(4) . . ?
C1 C2 C3 120.2(4) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 118.9(4) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
O2 C6 C1 110.7(3) . . ?
O2 C6 C7 108.5(3) . . ?
C1 C6 C7 109.8(4) . . ?
O2 C6 C8 107.2(3) . . ?
C1 C6 C8 108.9(4) . . ?
C7 C6 C8 111.7(5) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 C10 120.7(3) . . ?
N2 C9 C14 118.3(3) . . ?
C10 C9 C14 121.0(3) . . ?
C11 C10 C9 120.6(4) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 118.4(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N2 C13 C12 122.3(3) . . ?
N2 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
O1 C14 C15 107.6(3) . . ?
O1 C14 C9 107.3(3) . . ?
C15 C14 C9 111.2(3) . . ?
O1 C14 C16 108.9(3) . . ?
C15 C14 C16 112.5(4) . . ?
C9 C14 C16 109.1(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
H3A O3 H3B 44.6 . . ?
H3C O3 H3D 106.4 . . ?
N1 C5 C4 122.0(4) . . ?
N1 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.651
_refine_diff_density_rms         0.104


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, pentane'
####################################################################### 
# 
# 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_4iv
_database_code_depnum_ccdc_archive 'CCDC 1497504'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'cis-Cl, cis-O, trans-N-bis(2-{pyridin-2-yl}propan-2-olato)-dichloro-iridium(IV)'
_chemical_name_common            'Ir(pyalk)2Cl2, "green isomer"'
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H20 Cl2 Ir N2 O2, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C18 H24 Cl2 Ir N2 O3'
_chemical_formula_weight         579.49

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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.90010(10)
_cell_length_b                   18.4626(3)
_cell_length_c                   14.3136(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.040(7)
_cell_angle_gamma                90
_cell_volume                     2079.66(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    18526
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      68.2

_exptl_crystal_description       Block
_exptl_crystal_colour            'Dark green'
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    14.959
_shelx_estimated_absorpt_T_min   0.154
_shelx_estimated_absorpt_T_max   0.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'


_exptl_special_details           
; 
 'Rigaku MicroMax-007HF, Rigaku Saturn 944+ CCD' 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'microfocus rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 22.2
_diffrn_reflns_number            60998
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.917
_diffrn_reflns_theta_max         68.353
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3812
_reflns_number_gt                3564
_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       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.0280P)²+8.9233P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3812
_refine_ls_number_parameters     269
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0700
_refine_ls_wR_factor_gt          0.0681
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.82676(2) 0.13967(2) 0.70574(2) 0.02526(8) Uani 1 1 d . . . . .
Cl1 Cl 0.91845(14) 0.12500(6) 0.55412(7) 0.0328(2) Uani 1 1 d . . . . .
Cl2 Cl 0.69295(15) 0.24900(6) 0.65570(8) 0.0349(3) Uani 1 1 d . . . . .
O1 O 0.7504(4) 0.15401(18) 0.8303(2) 0.0331(7) Uani 1 1 d . . . . .
C15 C 0.8227(8) -0.0402(3) 0.8361(4) 0.0509(14) Uani 1 1 d . . . . .
H15A H 0.9347 -0.0469 0.8702 0.076 Uiso 1 1 calc R U . . .
H15B H 0.7610 -0.0863 0.8335 0.076 Uiso 1 1 calc R U . . .
H15C H 0.7584 -0.0040 0.8685 0.076 Uiso 1 1 calc R U . . .
O2 O 0.9424(4) 0.05052(17) 0.7437(2) 0.0321(7) Uani 1 1 d . . . . .
N1 N 1.0276(5) 0.1998(2) 0.7596(3) 0.0275(8) Uani 1 1 d . . . . .
N2 N 0.6313(5) 0.0701(2) 0.6666(3) 0.0305(8) Uani 1 1 d . . . . .
C13 C 0.6710(6) 0.0002(3) 0.6861(3) 0.0337(10) Uani 1 1 d . . . . .
C5 C 1.0223(6) 0.2156(2) 0.8516(3) 0.0305(10) Uani 1 1 d . . . . .
C14 C 0.8446(6) -0.0143(3) 0.7366(4) 0.0339(10) Uani 1 1 d . . . . .
C6 C 0.8697(6) 0.1870(3) 0.8977(3) 0.0315(10) Uani 1 1 d . . . . .
C1 C 1.1571(6) 0.2225(3) 0.7127(4) 0.0386(11) Uani 1 1 d . . . . .
H1 H 1.1570 0.2114 0.6478 0.046 Uiso 1 1 calc R U . . .
C12 C 0.5520(7) -0.0533(3) 0.6609(4) 0.0417(12) Uani 1 1 d . . . . .
H12 H 0.5782 -0.1026 0.6741 0.050 Uiso 1 1 calc R U . . .
C9 C 0.4783(6) 0.0884(3) 0.6255(4) 0.0366(11) Uani 1 1 d . . . . .
H9 H 0.4526 0.1381 0.6140 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9287(8) 0.1304(3) 0.9712(4) 0.0467(14) Uani 1 1 d . . . . .
H7A H 0.8305 0.1122 1.0014 0.070 Uiso 1 1 calc R U . . .
H7B H 1.0098 0.1525 1.0186 0.070 Uiso 1 1 calc R U . . .
H7C H 0.9836 0.0902 0.9409 0.070 Uiso 1 1 calc R U . . .
C2AA C 1.2896(7) 0.2759(3) 0.8499(4) 0.0437(13) Uani 1 1 d . . . . .
H2AA H 1.3823 0.3013 0.8816 0.052 Uiso 1 1 calc R U . . .
C11 C 0.3963(7) -0.0348(3) 0.6170(4) 0.0456(13) Uani 1 1 d . . . . .
H11 H 0.3154 -0.0713 0.5986 0.055 Uiso 1 1 calc R U . . .
C1AA C 1.1545(6) 0.2538(3) 0.8985(4) 0.0356(11) Uani 1 1 d . . . . .
H1AA H 1.1527 0.2646 0.9633 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7763(7) 0.2492(3) 0.9417(4) 0.0441(13) Uani 1 1 d . . . . .
H8A H 0.7361 0.2838 0.8928 0.066 Uiso 1 1 calc R U . . .
H8B H 0.8539 0.2737 0.9887 0.066 Uiso 1 1 calc R U . . .
H8C H 0.6791 0.2299 0.9718 0.066 Uiso 1 1 calc R U . . .
C16 C 0.9447(7) -0.0685(3) 0.6839(5) 0.0596(18) Uani 1 1 d . . . . .
H16A H 1.0604 -0.0723 0.7143 0.089 Uiso 1 1 calc R U . . .
H16B H 0.9491 -0.0522 0.6190 0.089 Uiso 1 1 calc R U . . .
H16C H 0.8892 -0.1159 0.6844 0.089 Uiso 1 1 calc R U . . .
C10 C 0.3587(7) 0.0371(3) 0.6000(4) 0.0438(13) Uani 1 1 d . . . . .
H10 H 0.2507 0.0508 0.5709 0.053 Uiso 1 1 calc R U . . .
C2 C 1.2893(7) 0.2612(3) 0.7556(4) 0.0458(13) Uani 1 1 d . . . . .
H2 H 1.3793 0.2776 0.7211 0.055 Uiso 1 1 calc R U . . .
C50A C 0.360(5) 1.0667(16) 0.873(2) 0.071(7) Uani 0.5 1 d D U P A -1
H50A H 0.3046 1.0621 0.8090 0.107 Uiso 0.5 1 calc R U P A -1
H50B H 0.4646 1.0953 0.8709 0.107 Uiso 0.5 1 calc R U P A -1
H50C H 0.2836 1.0909 0.9128 0.107 Uiso 0.5 1 calc R U P A -1
C51A C 0.4051(16) 0.9908(8) 0.9123(9) 0.057(3) Uani 0.5 1 d D U P A -1
C52A C 0.5591(17) 0.9305(7) 1.0389(8) 0.057(3) Uani 0.5 1 d D U P A -1
H52A H 0.6306 0.9066 0.9946 0.069 Uiso 0.5 1 calc R U P A -1
H52B H 0.4622 0.8987 1.0505 0.069 Uiso 0.5 1 calc R U P A -1
C53A C 0.663(4) 0.9525(14) 1.1305(17) 0.059(7) Uani 0.5 1 d D U P A -1
H53A H 0.5926 0.9832 1.1677 0.089 Uiso 0.5 1 calc R U P A -1
H53B H 0.7638 0.9794 1.1158 0.089 Uiso 0.5 1 calc R U P A -1
H53C H 0.6971 0.9090 1.1664 0.089 Uiso 0.5 1 calc R U P A -1
O1A O 0.3604(13) 0.9335(6) 0.8774(7) 0.075(3) Uani 0.5 1 d . U P A -1
O2A O 0.50(2) 1.004(3) 1.005(7) 0.057(5) Uani 0.5 1 d D U P A -1


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 O2 1.937(3) . ?
Ir1 O1 1.950(3) . ?
Ir1 N1 2.032(4) . ?
Ir1 N2 2.048(4) . ?
Ir1 Cl2 2.3604(11) . ?
Ir1 Cl1 2.3630(11) . ?
O1 C6 1.425(5) . ?
C15 C14 1.526(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C14 1.423(6) . ?
N1 C1 1.340(6) . ?
N1 C5 1.353(6) . ?
N2 C9 1.340(6) . ?
N2 C13 1.352(6) . ?
C13 C12 1.388(7) . ?
C13 C14 1.518(7) . ?
C5 C1AA 1.385(7) . ?
C5 C6 1.519(7) . ?
C14 C16 1.516(7) . ?
C6 C7 1.527(7) . ?
C6 C8 1.530(7) . ?
C1 C2 1.366(7) . ?
C1 H1 0.9500 . ?
C12 C11 1.374(8) . ?
C12 H12 0.9500 . ?
C9 C10 1.366(7) . ?
C9 H9 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C2AA C2 1.377(8) . ?
C2AA C1AA 1.386(7) . ?
C2AA H2AA 0.9500 . ?
C11 C10 1.377(8) . ?
C11 H11 0.9500 . ?
C1AA H1AA 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C10 H10 0.9500 . ?
C2 H2 0.9500 . ?
C50A C51A 1.54(2) . ?
C50A H50A 0.9800 . ?
C50A H50B 0.9800 . ?
C50A H50C 0.9800 . ?
C51A O1A 1.210(17) . ?
C51A O2A 1.50(4) . ?
C52A O2A 1.49(4) . ?
C52A C53A 1.54(2) . ?
C52A H52A 0.9900 . ?
C52A H52B 0.9900 . ?
C53A H53A 0.9800 . ?
C53A H53B 0.9800 . ?
C53A H53C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Ir1 O1 92.01(14) . . ?
O2 Ir1 N1 91.41(14) . . ?
O1 Ir1 N1 82.70(14) . . ?
O2 Ir1 N2 82.51(14) . . ?
O1 Ir1 N2 92.81(14) . . ?
N1 Ir1 N2 172.33(15) . . ?
O2 Ir1 Cl2 178.00(10) . . ?
O1 Ir1 Cl2 89.72(10) . . ?
N1 Ir1 Cl2 87.82(11) . . ?
N2 Ir1 Cl2 98.41(11) . . ?
O2 Ir1 Cl1 89.14(10) . . ?
O1 Ir1 Cl1 178.76(10) . . ?
N1 Ir1 Cl1 96.84(11) . . ?
N2 Ir1 Cl1 87.78(11) . . ?
Cl2 Ir1 Cl1 89.12(4) . . ?
C6 O1 Ir1 116.0(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 O2 Ir1 117.1(3) . . ?
C1 N1 C5 120.7(4) . . ?
C1 N1 Ir1 125.9(3) . . ?
C5 N1 Ir1 113.4(3) . . ?
C9 N2 C13 121.0(4) . . ?
C9 N2 Ir1 126.2(3) . . ?
C13 N2 Ir1 112.7(3) . . ?
N2 C13 C12 119.1(5) . . ?
N2 C13 C14 116.8(4) . . ?
C12 C13 C14 124.2(5) . . ?
N1 C5 C1AA 119.7(4) . . ?
N1 C5 C6 116.2(4) . . ?
C1AA C5 C6 124.0(4) . . ?
O2 C14 C16 106.6(4) . . ?
O2 C14 C13 110.4(4) . . ?
C16 C14 C13 111.6(4) . . ?
O2 C14 C15 107.6(4) . . ?
C16 C14 C15 111.4(5) . . ?
C13 C14 C15 109.2(4) . . ?
O1 C6 C5 110.9(4) . . ?
O1 C6 C7 108.5(4) . . ?
C5 C6 C7 109.3(4) . . ?
O1 C6 C8 106.6(4) . . ?
C5 C6 C8 110.4(4) . . ?
C7 C6 C8 111.1(4) . . ?
N1 C1 C2 121.7(5) . . ?
N1 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C11 C12 C13 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N2 C9 C10 121.2(5) . . ?
N2 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C2AA C1AA 119.9(5) . . ?
C2 C2AA H2AA 120.0 . . ?
C1AA C2AA H2AA 120.0 . . ?
C12 C11 C10 119.4(5) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C5 C1AA C2AA 119.2(5) . . ?
C5 C1AA H1AA 120.4 . . ?
C2AA C1AA H1AA 120.4 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C9 C10 C11 119.2(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 H10 120.4 . . ?
C1 C2 C2AA 118.7(5) . . ?
C1 C2 H2 120.7 . . ?
C2AA C2 H2 120.7 . . ?
C51A C50A H50A 109.5 . . ?
C51A C50A H50B 109.5 . . ?
H50A C50A H50B 109.5 . . ?
C51A C50A H50C 109.5 . . ?
H50A C50A H50C 109.5 . . ?
H50B C50A H50C 109.5 . . ?
O1A C51A O2A 128(2) . . ?
O1A C51A C50A 126.5(16) . . ?
O2A C51A C50A 105(3) . . ?
O2A C52A C53A 99(2) . . ?
O2A C52A H52A 112.0 . . ?
C53A C52A H52A 112.0 . . ?
O2A C52A H52B 112.0 . . ?
C53A C52A H52B 112.0 . . ?
H52A C52A H52B 109.6 . . ?
C52A C53A H53A 109.5 . . ?
C52A C53A H53B 109.5 . . ?
H53A C53A H53B 109.5 . . ?
C52A C53A H53C 109.5 . . ?
H53A C53A H53C 109.5 . . ?
H53B C53A H53C 109.5 . . ?
C52A O2A C51A 105(4) . . ?

_refine_diff_density_max         0.901
_refine_diff_density_min         -0.946
_refine_diff_density_rms         0.118


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate, pentane'
####################################################################### 
# 
# 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 1497505'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            'Ir(pyalk)2Cl2, "red isomer"'
_chemical_name_systematic        
'cis-Cl, cis-O, cis-N-bis(2-{pyridin-2-yl}propan-2-olato)-dichloro-iridium(IV)'
_chemical_formula_moiety         'C16 H20 Cl2 Ir N2 O2, C H2 Cl2'
_chemical_formula_sum            'C17 H22 Cl4 Ir N2 O2'
_chemical_formula_weight         620.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.7599(2)
_cell_length_b                   15.6388(3)
_cell_length_c                   15.6017(11)
_cell_angle_alpha                90
_cell_angle_beta                 98.373(7)
_cell_angle_gamma                90
_cell_volume                     2114.56(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    48310
_cell_measurement_temperature    93
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.342
_shelx_estimated_absorpt_T_min   0.342
_exptl_absorpt_coefficient_mu    6.834
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Dark red'
_exptl_crystal_density_diffrn    1.949
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1196
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            63497
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.141
_diffrn_ambient_temperature      93
_diffrn_detector                 RX
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
scan:
	Number of images: 90
	           Slice: 20.0000 - 200.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0226
scan:
	Number of images: 90
	           Slice: 20.0000 - 200.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 127.4000
	          2theta: -0.0226
scan:
	Number of images: 90
	           Slice: 20.0000 - 200.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 0.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: -0.0226
scan:
	Number of images: 90
	           Slice: 20.0000 - 200.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 127.4000
	          2theta: -0.0226
scan:
	Number of images: 90
	           Slice: 20.0000 - 200.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 127.4000
	          2theta: -0.0226
scan:
	Number of images: 90
	           Slice: 20.0000 - 200.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 90.0000
	             XTD: 127.4000
	          2theta: -0.0226
scan:
	Number of images: 90
	           Slice: 20.0000 - 200.0000
	     Image width: 2.0000
	        Exp time: 60.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 180.0000
	             XTD: 127.4000
	          2theta: -0.0226
;
_diffrn_measurement_device       
;
Crystal Goniometer
;
_diffrn_measurement_device_type  
;
Rigaku RAXIS conversion
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Unknown
_diffrn_orient_matrix_type       FS_PROCESS
_diffrn_orient_matrix_UB_11      -0.082953
_diffrn_orient_matrix_UB_12      -0.031302
_diffrn_orient_matrix_UB_13      0.024848
_diffrn_orient_matrix_UB_21      -0.062182
_diffrn_orient_matrix_UB_22      0.053773
_diffrn_orient_matrix_UB_23      -0.001937
_diffrn_orient_matrix_UB_31      -0.050658
_diffrn_orient_matrix_UB_32      -0.014748
_diffrn_orient_matrix_UB_33      -0.059800
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4462
_reflns_number_total             4846
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.829
_refine_diff_density_min         -0.767
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0203
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0120P)²+3.9660P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0409
_refine_ls_wR_factor_ref         0.0418
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H3(0.038) H2(0.034) H4(0.035) H12(0.033) H1(0.029) H11(0.038)
 H9(0.033) H10(0.038) H16A(0.047) H16B(0.047) H16C(0.047) H15A(0.052)
 H15B(0.052) H15C(0.052) H7A(0.052) H7B(0.052) H7C(0.052) H17A(0.053)
 H17B(0.053) H8A(0.055) H8B(0.055) H8C(0.055)
 Fixed X: H3(0.3322) H2(0.5426) H4(0.1258) H12(0.8866) H1(0.5415) H11(0.9685)
 H9(0.5269) H10(0.7854) H16A(0.5677) H16B(0.7299) H16C(0.584) H15A(0.62)
 H15B(0.7753) H15C(0.6499) H7A(-0.1424) H7B(-0.0861) H7C(-0.0429) H17A(0.281)
 H17B(0.2068) H8A(0.1558) H8B(0.0272) H8C(-0.0161)
 Fixed Y: H3(0.0573) H2(0.1481) H4(0.064) H12(0.2493) H1(0.2405) H11(0.3748)
 H9(0.4352) H10(0.4702) H16A(0.2442) H16B(0.2014) H16C(0.1445) H15A(0.0588)
 H15B(0.108) H15C(0.1054) H7A(0.1979) H7B(0.1621) H7C(0.2555) H17A(0.6435)
 H17B(0.6624) H8A(0.0588) H8B(0.0378) H8C(0.0839)
 Fixed Z: H3(0.1878) H2(0.2252) H4(0.2653) H12(0.5692) H1(0.3399) H11(0.5112)
 H9(0.4314) H10(0.444) H16A(0.687) H16B(0.6886) H16C(0.6933) H15A(0.563)
 H15B(0.5607) H15C(0.478) H7A(0.3836) H7B(0.2998) H7C(0.3308) H17A(0.8787)
 H17B(0.7829) H8A(0.4773) H8B(0.3994) H8C(0.4818)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.32882(2) 0.27943(2) 0.47792(2) 0.01828(4) Uani 1 1 d . . . . .
Cl1 Cl 0.22450(9) 0.39238(5) 0.39057(5) 0.02892(16) Uani 1 1 d . . . . .
Cl2 Cl 0.29631(9) 0.35213(5) 0.60544(5) 0.02889(16) Uani 1 1 d . . . . .
Cl4 Cl 0.45387(11) 0.61755(6) 0.78682(7) 0.0470(2) Uani 1 1 d . . . . .
Cl5 Cl 0.18106(12) 0.52225(7) 0.81399(9) 0.0645(3) Uani 1 1 d . . . . .
O1 O 0.1293(2) 0.22309(13) 0.47369(13) 0.0230(4) Uani 1 1 d . . . . .
O2 O 0.4319(2) 0.18272(13) 0.54137(14) 0.0259(4) Uani 1 1 d . . . . .
C3 C 0.3337(4) 0.0956(2) 0.2335(2) 0.0320(7) Uani 1 1 d . . . . .
H3 H 0.3322 0.0573 0.1878 0.038 Uiso 1 1 calc R . . . .
C2 C 0.4592(4) 0.1493(2) 0.25586(19) 0.0287(7) Uani 1 1 d . . . . .
H2 H 0.5426 0.1481 0.2252 0.034 Uiso 1 1 calc R . . . .
N1 N 0.3386(3) 0.20781(15) 0.36979(15) 0.0202(5) Uani 1 1 d . . . . .
C4 C 0.2108(4) 0.0995(2) 0.2799(2) 0.0288(7) Uani 1 1 d . . . . .
H4 H 0.1258 0.0640 0.2653 0.035 Uiso 1 1 calc R . . . .
C12 C 0.8148(3) 0.2874(2) 0.5409(2) 0.0276(6) Uani 1 1 d . . . . .
H12 H 0.8866 0.2493 0.5692 0.033 Uiso 1 1 calc R . . . .
N2 N 0.5536(3) 0.32357(15) 0.49092(15) 0.0222(5) Uani 1 1 d . . . . .
C1 C 0.4576(3) 0.20443(19) 0.32446(19) 0.0242(6) Uani 1 1 d . . . . .
H1 H 0.5415 0.2405 0.3399 0.029 Uiso 1 1 calc R . . . .
C13 C 0.6583(3) 0.26893(18) 0.53286(17) 0.0212(6) Uani 1 1 d . . . . .
C5 C 0.2151(3) 0.15689(18) 0.34845(18) 0.0211(6) Uani 1 1 d . . . . .
C6 C 0.0873(3) 0.16492(19) 0.40392(18) 0.0231(6) Uani 1 1 d . . . . .
C14 C 0.5937(3) 0.18926(18) 0.57023(18) 0.0213(6) Uani 1 1 d . . . . .
C11 C 0.8638(4) 0.3624(2) 0.5069(2) 0.0316(7) Uani 1 1 d . . . . .
H11 H 0.9685 0.3748 0.5112 0.038 Uiso 1 1 calc R . . . .
C9 C 0.6003(4) 0.39749(19) 0.4590(2) 0.0279(6) Uani 1 1 d . . . . .
H9 H 0.5269 0.4352 0.4314 0.033 Uiso 1 1 calc R . . . .
C10 C 0.7551(4) 0.4187(2) 0.4662(2) 0.0316(7) Uani 1 1 d . . . . .
H10 H 0.7854 0.4702 0.4440 0.038 Uiso 1 1 calc R . . . .
C16 C 0.6214(4) 0.1954(2) 0.6689(2) 0.0312(7) Uani 1 1 d . . . . .
H16A H 0.5677 0.2442 0.6870 0.047 Uiso 1 1 calc GR . . . .
H16B H 0.7299 0.2014 0.6886 0.047 Uiso 1 1 calc GR . . . .
H16C H 0.5840 0.1445 0.6933 0.047 Uiso 1 1 calc GR . . . .
C15 C 0.6665(4) 0.1078(2) 0.5402(2) 0.0350(7) Uani 1 1 d . . . . .
H15A H 0.6200 0.0588 0.5630 0.052 Uiso 1 1 calc GR . . . .
H15B H 0.7753 0.1080 0.5607 0.052 Uiso 1 1 calc GR . . . .
H15C H 0.6499 0.1054 0.4780 0.052 Uiso 1 1 calc GR . . . .
C7 C -0.0597(4) 0.1982(2) 0.3495(2) 0.0345(7) Uani 1 1 d . . . . .
H7A H -0.1424 0.1979 0.3836 0.052 Uiso 1 1 calc GR . . . .
H7B H -0.0861 0.1621 0.2998 0.052 Uiso 1 1 calc GR . . . .
H7C H -0.0429 0.2555 0.3308 0.052 Uiso 1 1 calc GR . . . .
C17 C 0.2708(4) 0.6224(2) 0.8196(3) 0.0444(9) Uani 1 1 d . . . . .
H17A H 0.2810 0.6435 0.8787 0.053 Uiso 1 1 calc R . . . .
H17B H 0.2068 0.6624 0.7829 0.053 Uiso 1 1 calc R . . . .
C8 C 0.0611(4) 0.0783(2) 0.4444(2) 0.0367(8) Uani 1 1 d . . . . .
H8A H 0.1558 0.0588 0.4773 0.055 Uiso 1 1 calc GR . . . .
H8B H 0.0272 0.0378 0.3994 0.055 Uiso 1 1 calc GR . . . .
H8C H -0.0161 0.0839 0.4818 0.055 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 Cl1 2.3345(7) . ?
Ir1 Cl2 2.3447(7) . ?
Ir1 O1 1.9499(19) . ?
Ir1 O2 1.9550(19) . ?
Ir1 N1 2.037(2) . ?
Ir1 N2 2.068(2) . ?
Cl4 C17 1.754(4) . ?
Cl5 C17 1.749(4) . ?
O1 C6 1.425(3) . ?
O2 C14 1.427(3) . ?
C3 C2 1.387(5) . ?
C3 C4 1.383(4) . ?
C2 C1 1.376(4) . ?
N1 C1 1.344(4) . ?
N1 C5 1.345(4) . ?
C4 C5 1.393(4) . ?
C12 C13 1.389(4) . ?
C12 C11 1.381(4) . ?
N2 C13 1.351(4) . ?
N2 C9 1.346(4) . ?
C13 C14 1.520(4) . ?
C5 C6 1.516(4) . ?
C6 C7 1.527(4) . ?
C6 C8 1.525(4) . ?
C14 C16 1.527(4) . ?
C14 C15 1.529(4) . ?
C11 C10 1.382(5) . ?
C9 C10 1.384(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
Cl1 Ir1 Cl2 92.45(3) . . ?
O1 Ir1 Cl1 92.83(6) . . ?
O1 Ir1 Cl2 91.65(6) . . ?
O1 Ir1 O2 90.76(8) . . ?
O1 Ir1 N1 82.47(9) . . ?
O1 Ir1 N2 171.87(9) . . ?
O2 Ir1 Cl1 173.51(6) . . ?
O2 Ir1 Cl2 92.85(7) . . ?
O2 Ir1 N1 85.53(9) . . ?
O2 Ir1 N2 81.12(9) . . ?
N1 Ir1 Cl1 89.58(7) . . ?
N1 Ir1 Cl2 173.87(7) . . ?
N1 Ir1 N2 96.35(9) . . ?
N2 Ir1 Cl1 95.21(7) . . ?
N2 Ir1 Cl2 89.22(7) . . ?
C6 O1 Ir1 116.38(16) . . ?
C14 O2 Ir1 117.95(17) . . ?
C4 C3 C2 119.4(3) . . ?
C1 C2 C3 118.5(3) . . ?
C1 N1 Ir1 125.9(2) . . ?
C1 N1 C5 120.3(2) . . ?
C5 N1 Ir1 113.66(18) . . ?
C3 C4 C5 119.6(3) . . ?
C11 C12 C13 120.0(3) . . ?
C13 N2 Ir1 113.94(18) . . ?
C9 N2 Ir1 125.9(2) . . ?
C9 N2 C13 120.1(2) . . ?
N1 C1 C2 122.1(3) . . ?
C12 C13 C14 123.7(3) . . ?
N2 C13 C12 120.2(3) . . ?
N2 C13 C14 116.1(2) . . ?
N1 C5 C4 120.1(3) . . ?
N1 C5 C6 116.3(2) . . ?
C4 C5 C6 123.5(3) . . ?
O1 C6 C5 111.1(2) . . ?
O1 C6 C7 108.0(2) . . ?
O1 C6 C8 106.8(2) . . ?
C5 C6 C7 110.1(2) . . ?
C5 C6 C8 109.3(2) . . ?
C8 C6 C7 111.5(3) . . ?
O2 C14 C13 110.3(2) . . ?
O2 C14 C16 109.1(2) . . ?
O2 C14 C15 106.4(2) . . ?
C13 C14 C16 108.8(2) . . ?
C13 C14 C15 111.7(2) . . ?
C16 C14 C15 110.4(3) . . ?
C12 C11 C10 119.1(3) . . ?
N2 C9 C10 121.5(3) . . ?
C11 C10 C9 119.1(3) . . ?
Cl5 C17 Cl4 111.7(2) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, ethyl acetate'
_chemical_properties_physical    ', Oxidizer: reduction-sensitive'
####################################################################### 
# 
# 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_4iii
_database_code_depnum_ccdc_archive 'CCDC 1497506'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_PLAT973_4iii                
;
PROBLEM: Check Calcd Positive Residual Density on     Ir1       2.62 eA-3        
RESPONSE: The Maximum Residual Density Peak (2.62 e/A3) is very close to 
a metallic heavy atom (Ir1, 0.93 A). This is a very common feature in 
structures containing heavy scatterers such as iridium and where multi-scan
 absorption correction has been employed. There is no reasonable chemical
 interpretation of this electron densities close to heavy atoms.
;



_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Hydrogen cis-Cl, cis-O, trans-N-bis(2-{pyridin-2-yl}propan-2-olato)-dichloro-iridate(III)'
_chemical_name_common            'Ir(pyalk)(Hpyalk)Cl2, green isomer'
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H21 Cl2 Ir N2 O2), C H2 Cl2, 2(H2 O)'
_chemical_formula_sum            'C33 H48 Cl6 Ir2 N4 O6'
_chemical_formula_weight         1193.85

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.044(7)
_cell_length_b                   13.823(9)
_cell_length_c                   17.039(13)
_cell_angle_alpha                90.000(16)
_cell_angle_beta                 95.227(13)
_cell_angle_gamma                90.000(19)
_cell_volume                     2121(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    496(2)
_cell_measurement_reflns_used    4809
_cell_measurement_theta_min      1.9
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    6.690
_shelx_estimated_absorpt_T_min   0.348
_shelx_estimated_absorpt_T_max   0.348
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.538
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'


_exptl_special_details           
; 
 'Rigaku SCX Mini, Rigaku Mercury275R CCD' 
;
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Mercury275R CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.8
_diffrn_reflns_number            29122
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.1016
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.900
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3748
_reflns_number_gt                3303
_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       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3748
_refine_ls_number_parameters     249
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_restrained_S_all      1.167
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir -0.05842(3) 0.22724(2) 0.70311(2) 0.02835(17) Uani 1 1 d . . . . .
N1 N -0.1686(7) 0.2836(4) 0.7927(4) 0.0331(14) Uani 1 1 d . . . . .
N2 N 0.0724(6) 0.1734(4) 0.6233(4) 0.0336(13) Uani 1 1 d . . . . .
O1 O -0.0243(5) 0.1157(3) 0.7845(3) 0.0341(11) Uani 1 1 d D . . . .
O2 O 0.1378(6) 0.2834(4) 0.7478(3) 0.0376(13) Uani 1 1 d . . . . .
C1 C -0.1624(9) 0.2306(5) 0.8603(5) 0.0324(19) Uani 1 1 d . . . . .
C2 C -0.2328(9) 0.2632(6) 0.9251(5) 0.0409(19) Uani 1 1 d . . . . .
H2 H -0.2297 0.2263 0.9709 0.049 Uiso 1 1 calc R U . . .
C3 C -0.3075(10) 0.3514(7) 0.9207(5) 0.049(2) Uani 1 1 d . . . . .
H3 H -0.3554 0.3737 0.9632 0.059 Uiso 1 1 calc R U . . .
C4 C -0.3097(8) 0.4048(6) 0.8531(5) 0.0455(19) Uani 1 1 d . . . . .
H4 H -0.3577 0.4644 0.8497 0.055 Uiso 1 1 calc R U . . .
C5 C -0.2403(8) 0.3700(6) 0.7895(5) 0.0406(17) Uani 1 1 d . . . . .
H5 H -0.2428 0.4067 0.7436 0.049 Uiso 1 1 calc R U . . .
C6 C -0.0767(8) 0.1351(5) 0.8626(4) 0.0338(16) Uani 1 1 d . . . . .
C7 C -0.1810(11) 0.0517(6) 0.8814(5) 0.054(2) Uani 1 1 d . . . . .
H7A H -0.2713 0.0558 0.8473 0.081 Uiso 1 1 calc R U . . .
H7B H -0.2033 0.0565 0.9353 0.081 Uiso 1 1 calc R U . . .
H7C H -0.1333 -0.0091 0.8733 0.081 Uiso 1 1 calc R U . . .
C8 C 0.0599(10) 0.1400(8) 0.9214(5) 0.057(2) Uani 1 1 d . . . . .
H8A H 0.1164 0.0815 0.9185 0.085 Uiso 1 1 calc R U . . .
H8B H 0.0297 0.1472 0.9737 0.085 Uiso 1 1 calc R U . . .
H8C H 0.1198 0.1943 0.9092 0.085 Uiso 1 1 calc R U . . .
C9 C 0.2227(8) 0.1952(5) 0.6379(4) 0.0342(15) Uani 1 1 d . . . . .
C10 C 0.3201(8) 0.1733(6) 0.5826(5) 0.0413(18) Uani 1 1 d . . . . .
H10 H 0.4203 0.1883 0.5923 0.050 Uiso 1 1 calc R U . . .
C11 C 0.2674(9) 0.1283(7) 0.5118(5) 0.050(2) Uani 1 1 d . . . . .
H11 H 0.3325 0.1132 0.4744 0.060 Uiso 1 1 calc R U . . .
C12 C 0.1177(9) 0.1065(6) 0.4978(4) 0.0432(18) Uani 1 1 d . . . . .
H12 H 0.0805 0.0771 0.4510 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0272(9) 0.1294(6) 0.5542(4) 0.0386(17) Uani 1 1 d . . . . .
H13 H -0.0729 0.1138 0.5448 0.046 Uiso 1 1 calc R U . . .
C14 C 0.2660(10) 0.2433(7) 0.7163(5) 0.0358(18) Uani 1 1 d . . . . .
C15 C 0.3374(10) 0.1663(7) 0.7722(5) 0.055(2) Uani 1 1 d . . . . .
H15A H 0.3690 0.1956 0.8221 0.082 Uiso 1 1 calc R U . . .
H15B H 0.4216 0.1388 0.7500 0.082 Uiso 1 1 calc R U . . .
H15C H 0.2663 0.1164 0.7798 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3747(9) 0.3258(7) 0.7068(5) 0.051(2) Uani 1 1 d . . . . .
H16A H 0.3310 0.3715 0.6691 0.076 Uiso 1 1 calc R U . . .
H16B H 0.4644 0.3006 0.6888 0.076 Uiso 1 1 calc R U . . .
H16C H 0.3970 0.3575 0.7567 0.076 Uiso 1 1 calc R U . . .
Cl1 Cl -0.1015(2) 0.35912(14) 0.61793(10) 0.0423(4) Uani 1 1 d . . . . .
Cl2 Cl -0.28576(19) 0.15156(15) 0.65018(11) 0.0416(4) Uani 1 1 d . . . . .
C50 C 0.5518(18) 0.4901(19) 0.5488(11) 0.069(6) Uani 0.5 1 d . . P A -1
H50A H 0.6535 0.4703 0.5635 0.082 Uiso 0.5 1 calc R U P A -1
H50B H 0.5026 0.4960 0.5968 0.082 Uiso 0.5 1 calc R U P A -1
Cl3 Cl 0.468(2) 0.4051(17) 0.4936(12) 0.125(7) Uani 0.5 1 d . . P A -1
Cl4 Cl 0.5533(17) 0.6054(12) 0.5024(7) 0.080(4) Uani 0.5 1 d . . P A -1
O3 O 0.1049(7) 0.4639(4) 0.7952(3) 0.0455(13) Uani 1 1 d D . . . .
H1 H 0.0174 0.0633 0.7817 0.055 Uiso 0.6117 1 d D U P B 1
H3A H 0.0995 0.4065 0.7827 0.055 Uiso 0.6117 1 d D U P B 1
H3B H 0.1885 0.4851 0.8078 0.055 Uiso 0.6117 1 d D U P B 1
H1B H 0.1042 0.3417 0.7587 0.055 Uiso 0.3883 1 d . U P B 2
H3C H 0.0466 0.4977 0.7671 0.055 Uiso 0.3883 1 d . U P B 2
H3D H 0.1738 0.4551 0.7676 0.055 Uiso 0.3883 1 d . U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 O2 2.021(6) . ?
Ir1 N2 2.024(6) . ?
Ir1 N1 2.051(6) . ?
Ir1 O1 2.077(5) . ?
Ir1 Cl1 2.340(2) . ?
Ir1 Cl2 2.408(2) . ?
N1 C5 1.358(10) . ?
N1 C1 1.362(10) . ?
N2 C13 1.355(9) . ?
N2 C9 1.392(9) . ?
O1 H1 0.8211 . ?
O1 C6 1.477(8) . ?
O1 H1 0.8211 . ?
O2 C14 1.434(10) . ?
O2 H1B 0.8868 . ?
C1 C2 1.398(11) . ?
C1 C6 1.530(11) . ?
C2 C3 1.393(12) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(10) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C8 1.520(11) . ?
C6 C7 1.541(11) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.380(11) . ?
C9 C14 1.512(11) . ?
C10 C11 1.401(12) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.356(10) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C16 1.524(12) . ?
C14 C15 1.531(12) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C50 Cl3 1.64(3) . ?
C50 Cl4 1.78(3) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?
O3 H3D 0.8238 . ?
O3 H3C 0.8239 . ?
O3 H3A 0.8217 . ?
O3 H3B 0.8207 . ?
O3 H3C 0.8239 . ?
O3 H3D 0.8238 . ?

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
O2 Ir1 N2 81.2(2) . . ?
O2 Ir1 N1 92.5(2) . . ?
N2 Ir1 N1 173.3(2) . . ?
O2 Ir1 O1 87.8(2) . . ?
N2 Ir1 O1 96.6(2) . . ?
N1 Ir1 O1 80.7(2) . . ?
O2 Ir1 Cl1 91.45(17) . . ?
N2 Ir1 Cl1 86.81(18) . . ?
N1 Ir1 Cl1 95.79(18) . . ?
O1 Ir1 Cl1 176.34(13) . . ?
O2 Ir1 Cl2 176.80(15) . . ?
N2 Ir1 Cl2 96.91(18) . . ?
N1 Ir1 Cl2 89.27(19) . . ?
O1 Ir1 Cl2 89.85(15) . . ?
Cl1 Ir1 Cl2 91.03(8) . . ?
C5 N1 C1 119.3(7) . . ?
C5 N1 Ir1 124.5(5) . . ?
C1 N1 Ir1 116.1(5) . . ?
C13 N2 C9 117.6(6) . . ?
C13 N2 Ir1 126.9(5) . . ?
C9 N2 Ir1 115.0(5) . . ?
H1 O1 C6 113.5 . . ?
H1 O1 Ir1 131.1 . . ?
C6 O1 Ir1 115.3(4) . . ?
H1 O1 H1 0.0 . . ?
C6 O1 H1 113.5 . . ?
Ir1 O1 H1 131.1 . . ?
C14 O2 Ir1 115.0(5) . . ?
C14 O2 H1B 137.2 . . ?
Ir1 O2 H1B 97.0 . . ?
N1 C1 C2 120.6(7) . . ?
N1 C1 C6 117.9(7) . . ?
C2 C1 C6 121.6(7) . . ?
C3 C2 C1 119.5(8) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.3(8) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 119.9(8) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 121.5(8) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
O1 C6 C8 107.1(6) . . ?
O1 C6 C1 109.7(6) . . ?
C8 C6 C1 111.0(7) . . ?
O1 C6 C7 107.7(6) . . ?
C8 C6 C7 111.9(7) . . ?
C1 C6 C7 109.4(6) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N2 120.3(7) . . ?
C10 C9 C14 124.7(7) . . ?
N2 C9 C14 115.0(7) . . ?
C9 C10 C11 119.8(7) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.7(7) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 118.1(8) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C12 C13 N2 124.6(8) . . ?
C12 C13 H13 117.7 . . ?
N2 C13 H13 117.7 . . ?
O2 C14 C9 110.4(7) . . ?
O2 C14 C16 107.5(7) . . ?
C9 C14 C16 110.7(7) . . ?
O2 C14 C15 110.2(7) . . ?
C9 C14 C15 107.8(7) . . ?
C16 C14 C15 110.3(8) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
Cl3 C50 Cl4 114.0(13) . . ?
Cl3 C50 H50A 108.8 . . ?
Cl4 C50 H50A 108.8 . . ?
Cl3 C50 H50B 108.8 . . ?
Cl4 C50 H50B 108.8 . . ?
H50A C50 H50B 107.6 . . ?
H3D O3 H3C 103.2 . . ?
H3A O3 H3B 116.3 . . ?
H3D O3 H3C 103.2 . . ?
H3C O3 H3C 0.0 . . ?
H3D O3 H3D 0.0 . . ?
H3C O3 H3D 103.2 . . ?
H3C O3 H3D 103.2 . . ?

_refine_diff_density_max         2.163
_refine_diff_density_min         -2.611
_refine_diff_density_rms         0.294


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, pentane'
_chemical_properties_physical    ', Air-sensitive,Oxygen-sensitive'
####################################################################### 
# 
# 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_8iv
_database_code_depnum_ccdc_archive 'CCDC 1497507'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;

# start Validation Reply Form


_vrf_PLAT910_8iv                 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min)          11 Note  
     
RESPONSE:Theta min = 3.0. This is the reason for the missing
reflections at low angle. It is not possible to increase the distance from the
crystal to the detector in this instrument (imaging plate), so we could not
collect useful additional images to overcome this alert. However this does not
present a problem since the high number of independent reflections (9438)
collected and the high data/parameter ratio (ca. 26).

;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'Sodium (2-{pyridin-2-yl}propan-2-olato)-tetrachloro-iridium(IV)'
_chemical_name_common            Na[Ir(pyalk)Cl4]
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H10 O1 Ir1 Cl4 1-), 2(Na 1+), 5(H2 O1)'
_chemical_formula_sum            'C16 H30 Cl8 Ir2 N2 Na2 O7'
_chemical_formula_weight         1076.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.4303(2)
_cell_length_b                   13.4446(3)
_cell_length_c                   14.3559(10)
_cell_angle_alpha                74.431(5)
_cell_angle_beta                 85.859(6)
_cell_angle_gamma                81.771(6)
_cell_volume                     1550.31(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    64910
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      30.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.306
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    9.330
_shelx_estimated_absorpt_T_min   0.204
_shelx_estimated_absorpt_T_max   0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.435
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn 944+ CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            86738
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.079
_diffrn_reflns_theta_max         30.505
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9438
_reflns_number_gt                8646
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+8.6885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9438
_refine_ls_number_parameters     368
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0586
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 1.2560(4) 0.0435(3) -0.0055(3) 0.0329(7) Uani 1 1 d D . . . .
Ir1 Ir 0.82973(2) 0.25989(2) 0.15588(2) 0.01619(4) Uani 1 1 d . . . . .
Ir2 Ir 1.29464(2) -0.25027(2) 0.34710(2) 0.01674(4) Uani 1 1 d . . . . .
Cl3 Cl 0.91784(13) 0.21542(8) 0.31352(7) 0.0258(2) Uani 1 1 d . . . . .
Cl8 Cl 1.21148(12) -0.35356(8) 0.25765(7) 0.02377(19) Uani 1 1 d . . . . .
Cl4 Cl 0.74276(12) 0.30994(8) -0.00276(7) 0.0251(2) Uani 1 1 d . . . . .
Cl1 Cl 0.83147(12) 0.08300(8) 0.16313(8) 0.0250(2) Uani 1 1 d . . . . .
Cl2 Cl 1.09437(12) 0.24702(8) 0.09655(8) 0.0256(2) Uani 1 1 d . . . . .
Cl5 Cl 1.42998(12) -0.15517(9) 0.20991(7) 0.0276(2) Uani 1 1 d . . . . .
Cl6 Cl 1.52550(12) -0.36641(8) 0.38870(8) 0.0259(2) Uani 1 1 d . . . . .
N1 N 0.8055(4) 0.4124(3) 0.1543(2) 0.0186(6) Uani 1 1 d . . . . .
C1 C 0.9214(5) 0.4741(3) 0.1285(3) 0.0226(8) Uani 1 1 d . . . . .
H1 H 1.0257 0.4456 0.1114 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6206(5) 0.5548(3) 0.1773(3) 0.0250(9) Uani 1 1 d . . . . .
H4 H 0.5151 0.5817 0.1939 0.030 Uiso 1 1 calc R U . . .
C3 C 0.7381(6) 0.6193(3) 0.1509(3) 0.0274(9) Uani 1 1 d . . . . .
H3 H 0.7148 0.6910 0.1492 0.033 Uiso 1 1 calc R U . . .
C2 C 0.8922(5) 0.5780(3) 0.1264(3) 0.0258(9) Uani 1 1 d . . . . .
H2 H 0.9755 0.6210 0.1087 0.031 Uiso 1 1 calc R U . . .
C5 C 0.6570(5) 0.4500(3) 0.1797(3) 0.0198(7) Uani 1 1 d . . . . .
Cl7 Cl 1.37262(13) -0.14928(8) 0.44134(8) 0.0269(2) Uani 1 1 d . . . . .
Na2 Na 1.1484(2) -0.01626(15) 0.15574(14) 0.0321(4) Uani 1 1 d . . . . .
Na1 Na 0.4903(3) 0.11384(19) 0.21171(16) 0.0452(5) Uani 1 1 d . . . . .
O2 O 1.0989(3) -0.1557(2) 0.3157(2) 0.0193(5) Uani 1 1 d . . . . .
N2 N 1.1559(4) -0.3226(2) 0.4593(2) 0.0181(6) Uani 1 1 d . . . . .
O6 O 0.5008(5) 0.1249(3) 0.0489(3) 0.0398(8) Uani 1 1 d D . . . .
O5 O 1.2384(4) 0.0603(3) 0.2705(3) 0.0326(7) Uani 1 1 d D . . . .
O1 O 0.6084(3) 0.2719(2) 0.2012(2) 0.0208(6) Uani 1 1 d . . . . .
C13 C 1.0021(5) -0.2783(3) 0.4581(3) 0.0190(7) Uani 1 1 d . . . . .
C11 C 0.9366(6) -0.4145(3) 0.5947(3) 0.0266(9) Uani 1 1 d . . . . .
H11 H 0.8606 -0.4463 0.6412 0.032 Uiso 1 1 calc R U . . .
C10 C 1.0954(5) -0.4588(3) 0.5956(3) 0.0251(9) Uani 1 1 d . . . . .
H10 H 1.1301 -0.5208 0.6433 0.030 Uiso 1 1 calc R U . . .
C14 C 0.9619(5) -0.1769(3) 0.3812(3) 0.0194(7) Uani 1 1 d . . . . .
C6 C 0.5382(5) 0.3722(3) 0.2120(3) 0.0205(8) Uani 1 1 d . . . . .
C9 C 1.2026(5) -0.4113(3) 0.5263(3) 0.0220(8) Uani 1 1 d . . . . .
H9 H 1.3114 -0.4420 0.5260 0.026 Uiso 1 1 calc R U . . .
C12 C 0.8904(5) -0.3238(3) 0.5253(3) 0.0246(8) Uani 1 1 d . . . . .
H12 H 0.7818 -0.2925 0.5237 0.030 Uiso 1 1 calc R U . . .
C15 C 0.8237(5) -0.1842(4) 0.3215(3) 0.0298(10) Uani 1 1 d . . . . .
H15A H 0.8031 -0.1195 0.2702 0.045 Uiso 1 1 calc R U . . .
H15B H 0.7272 -0.1949 0.3634 0.045 Uiso 1 1 calc R U . . .
H15C H 0.8519 -0.2428 0.2925 0.045 Uiso 1 1 calc R U . . .
O4 O 1.0314(4) -0.1431(3) 0.1013(2) 0.0317(7) Uani 1 1 d D . . . .
O7 O 0.5494(6) 0.0702(4) 0.3716(3) 0.0543(11) Uani 1 1 d D . . . .
C16 C 0.9236(6) -0.0875(3) 0.4298(3) 0.0278(9) Uani 1 1 d . . . . .
H16A H 1.0160 -0.0842 0.4660 0.042 Uiso 1 1 calc R U . . .
H16B H 0.8302 -0.0994 0.4742 0.042 Uiso 1 1 calc R U . . .
H16C H 0.9000 -0.0217 0.3803 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3897(6) 0.4052(4) 0.1503(4) 0.0355(11) Uani 1 1 d . . . . .
H8A H 0.3359 0.4724 0.1579 0.053 Uiso 1 1 calc R U . . .
H8B H 0.3160 0.3527 0.1713 0.053 Uiso 1 1 calc R U . . .
H8C H 0.4220 0.4119 0.0821 0.053 Uiso 1 1 calc R U . . .
H5A H 1.250(8) 0.015(4) 0.323(3) 0.053 Uiso 1 1 d D U . . .
H5B H 1.157(5) 0.101(4) 0.279(5) 0.053 Uiso 1 1 d D U . . .
H3A H 1.186(6) 0.074(4) -0.046(4) 0.053 Uiso 1 1 d D U . . .
H3B H 1.303(7) -0.005(4) -0.028(4) 0.053 Uiso 1 1 d D U . . .
H6A H 0.524(8) 0.184(3) 0.018(4) 0.053 Uiso 1 1 d D U . . .
H6B H 0.425(5) 0.115(5) 0.018(4) 0.053 Uiso 1 1 d D U . . .
H7D H 0.535(8) 0.009(3) 0.405(4) 0.053 Uiso 1 1 d D U . . .
H4A H 1.078(7) -0.168(5) 0.057(3) 0.053 Uiso 1 1 d D U . . .
H4B H 1.050(8) -0.193(3) 0.149(3) 0.053 Uiso 1 1 d D U . . .
C7 C 0.4934(6) 0.3587(4) 0.3198(3) 0.0320(10) Uani 1 1 d . . . . .
H7A H 0.4138 0.3099 0.3398 0.048 Uiso 1 1 calc R U . . .
H7B H 0.4483 0.4262 0.3305 0.048 Uiso 1 1 calc R U . . .
H7C H 0.5895 0.3314 0.3578 0.048 Uiso 1 1 calc R U . . .
H7E H 0.625(5) 0.095(5) 0.390(4) 0.048 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 Na2 2.395(4) . ?
O3 H3A 0.84(2) . ?
O3 H3B 0.84(2) . ?
Ir1 O1 1.930(3) . ?
Ir1 N1 2.025(3) . ?
Ir1 Cl3 2.3281(10) . ?
Ir1 Cl2 2.3295(10) . ?
Ir1 Cl4 2.3355(10) . ?
Ir1 Cl1 2.3504(10) . ?
Ir1 Na1 3.622(2) . ?
Ir2 O2 1.934(3) . ?
Ir2 N2 2.030(3) . ?
Ir2 Cl6 2.3195(10) . ?
Ir2 Cl8 2.3312(10) . ?
Ir2 Cl7 2.3401(11) . ?
Ir2 Cl5 2.3574(10) . ?
Ir2 Na2 3.7020(19) . ?
Cl1 Na2 2.819(2) . ?
Cl1 Na1 2.908(2) . ?
Cl5 Na2 2.819(2) . ?
N1 C1 1.340(5) . ?
N1 C5 1.345(5) . ?
C1 C2 1.376(6) . ?
C1 H1 0.9500 . ?
C4 C3 1.376(6) . ?
C4 C5 1.390(6) . ?
C4 H4 0.9500 . ?
C3 C2 1.397(6) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C5 C6 1.512(6) . ?
Na2 O5 2.381(4) . ?
Na2 O4 2.409(4) . ?
Na2 O2 2.596(3) . ?
Na2 Na1 3.814(3) 1_655 ?
Na2 H5B 2.68(6) . ?
Na2 H4B 2.66(6) . ?
Na1 O7 2.285(5) . ?
Na1 O6 2.297(4) . ?
Na1 O5 2.365(4) 1_455 ?
Na1 O1 2.437(4) . ?
Na1 Na2 3.814(3) 1_455 ?
O2 C14 1.446(5) . ?
N2 C9 1.345(5) . ?
N2 C13 1.346(5) . ?
O6 H6A 0.85(2) . ?
O6 H6B 0.845(19) . ?
O5 Na1 2.365(4) 1_655 ?
O5 H5A 0.839(19) . ?
O5 H5B 0.833(19) . ?
O1 C6 1.437(5) . ?
C13 C12 1.381(6) . ?
C13 C14 1.519(5) . ?
C11 C12 1.379(6) . ?
C11 C10 1.384(6) . ?
C11 H11 0.9500 . ?
C10 C9 1.381(6) . ?
C10 H10 0.9500 . ?
C14 C15 1.524(6) . ?
C14 C16 1.531(6) . ?
C6 C8 1.529(6) . ?
C6 C7 1.535(6) . ?
C9 H9 0.9500 . ?
C12 H12 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O4 H4A 0.84(2) . ?
O4 H4B 0.831(19) . ?
O7 H7D 0.85(2) . ?
O7 H7E 0.85(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Na2 O3 H3A 114(5) . . ?
Na2 O3 H3B 113(4) . . ?
H3A O3 H3B 104(6) . . ?
O1 Ir1 N1 82.74(13) . . ?
O1 Ir1 Cl3 91.41(9) . . ?
N1 Ir1 Cl3 89.75(10) . . ?
O1 Ir1 Cl2 178.31(9) . . ?
N1 Ir1 Cl2 97.18(10) . . ?
Cl3 Ir1 Cl2 90.27(4) . . ?
O1 Ir1 Cl4 88.85(9) . . ?
N1 Ir1 Cl4 88.49(10) . . ?
Cl3 Ir1 Cl4 178.18(4) . . ?
Cl2 Ir1 Cl4 89.47(4) . . ?
O1 Ir1 Cl1 91.66(9) . . ?
N1 Ir1 Cl1 174.39(10) . . ?
Cl3 Ir1 Cl1 90.41(4) . . ?
Cl2 Ir1 Cl1 88.43(4) . . ?
Cl4 Ir1 Cl1 91.38(4) . . ?
O1 Ir1 Na1 38.75(9) . . ?
N1 Ir1 Na1 121.17(10) . . ?
Cl3 Ir1 Na1 95.77(5) . . ?
Cl2 Ir1 Na1 141.10(5) . . ?
Cl4 Ir1 Na1 85.56(5) . . ?
Cl1 Ir1 Na1 53.24(5) . . ?
O2 Ir2 N2 82.71(12) . . ?
O2 Ir2 Cl6 178.32(9) . . ?
N2 Ir2 Cl6 95.61(9) . . ?
O2 Ir2 Cl8 89.03(9) . . ?
N2 Ir2 Cl8 87.66(10) . . ?
Cl6 Ir2 Cl8 90.94(4) . . ?
O2 Ir2 Cl7 90.69(9) . . ?
N2 Ir2 Cl7 90.39(10) . . ?
Cl6 Ir2 Cl7 89.28(4) . . ?
Cl8 Ir2 Cl7 178.05(4) . . ?
O2 Ir2 Cl5 91.18(8) . . ?
N2 Ir2 Cl5 173.79(10) . . ?
Cl6 Ir2 Cl5 90.50(4) . . ?
Cl8 Ir2 Cl5 91.19(4) . . ?
Cl7 Ir2 Cl5 90.75(4) . . ?
O2 Ir2 Na2 41.61(9) . . ?
N2 Ir2 Na2 124.27(10) . . ?
Cl6 Ir2 Na2 140.07(4) . . ?
Cl8 Ir2 Na2 89.03(4) . . ?
Cl7 Ir2 Na2 92.04(4) . . ?
Cl5 Ir2 Na2 49.58(4) . . ?
Ir1 Cl1 Na2 110.68(6) . . ?
Ir1 Cl1 Na1 86.39(6) . . ?
Na2 Cl1 Na1 160.15(8) . . ?
Ir2 Cl5 Na2 90.87(5) . . ?
C1 N1 C5 120.9(4) . . ?
C1 N1 Ir1 125.3(3) . . ?
C5 N1 Ir1 113.8(3) . . ?
N1 C1 C2 121.2(4) . . ?
N1 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C3 C2 119.1(4) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C1 C2 C3 118.9(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
N1 C5 C4 120.1(4) . . ?
N1 C5 C6 116.3(3) . . ?
C4 C5 C6 123.6(4) . . ?
O5 Na2 O3 114.71(14) . . ?
O5 Na2 O4 156.40(15) . . ?
O3 Na2 O4 87.85(14) . . ?
O5 Na2 O2 79.23(12) . . ?
O3 Na2 O2 154.54(14) . . ?
O4 Na2 O2 77.23(12) . . ?
O5 Na2 Cl1 93.58(10) . . ?
O3 Na2 Cl1 107.98(11) . . ?
O4 Na2 Cl1 85.31(10) . . ?
O2 Na2 Cl1 91.44(9) . . ?
O5 Na2 Cl5 81.25(10) . . ?
O3 Na2 Cl5 91.14(11) . . ?
O4 Na2 Cl5 91.97(10) . . ?
O2 Na2 Cl5 69.19(8) . . ?
Cl1 Na2 Cl5 160.53(9) . . ?
O5 Na2 Ir2 78.69(9) . . ?
O3 Na2 Ir2 128.46(11) . . ?
O4 Na2 Ir2 81.73(9) . . ?
O2 Na2 Ir2 29.66(6) . . ?
Cl1 Na2 Ir2 121.09(7) . . ?
Cl5 Na2 Ir2 39.55(3) . . ?
O5 Na2 Na1 36.38(10) . 1_655 ?
O3 Na2 Na1 81.34(10) . 1_655 ?
O4 Na2 Na1 155.51(12) . 1_655 ?
O2 Na2 Na1 103.96(9) . 1_655 ?
Cl1 Na2 Na1 118.90(7) . 1_655 ?
Cl5 Na2 Na1 66.50(6) . 1_655 ?
Ir2 Na2 Na1 87.88(5) . 1_655 ?
O5 Na2 H5B 17.7(8) . . ?
O3 Na2 H5B 118.4(14) . . ?
O4 Na2 H5B 151.2(12) . . ?
O2 Na2 H5B 81.6(14) . . ?
Cl1 Na2 H5B 75.9(8) . . ?
Cl5 Na2 H5B 98.5(8) . . ?
Ir2 Na2 H5B 89.4(12) . . ?
Na1 Na2 H5B 49.7(10) 1_655 . ?
O5 Na2 H4B 139.4(8) . . ?
O3 Na2 H4B 101.4(11) . . ?
O4 Na2 H4B 18.0(7) . . ?
O2 Na2 H4B 60.4(9) . . ?
Cl1 Na2 H4B 92.4(13) . . ?
Cl5 Na2 H4B 79.9(12) . . ?
Ir2 Na2 H4B 64.0(8) . . ?
Na1 Na2 H4B 146.4(11) 1_655 . ?
H5B Na2 H4B 140.2(18) . . ?
O7 Na1 O6 162.8(2) . . ?
O7 Na1 O5 84.35(17) . 1_455 ?
O6 Na1 O5 105.75(15) . 1_455 ?
O7 Na1 O1 85.23(15) . . ?
O6 Na1 O1 97.20(14) . . ?
O5 Na1 O1 132.91(15) 1_455 . ?
O7 Na1 Cl1 89.04(15) . . ?
O6 Na1 Cl1 75.95(12) . . ?
O5 Na1 Cl1 155.27(14) 1_455 . ?
O1 Na1 Cl1 69.85(9) . . ?
O7 Na1 Ir1 89.20(14) . . ?
O6 Na1 Ir1 84.81(11) . . ?
O5 Na1 Ir1 162.31(13) 1_455 . ?
O1 Na1 Ir1 29.72(7) . . ?
Cl1 Na1 Ir1 40.36(3) . . ?
O7 Na1 Na2 114.37(14) . 1_455 ?
O6 Na1 Na2 71.20(11) . 1_455 ?
O5 Na1 Na2 36.66(10) 1_455 1_455 ?
O1 Na1 Na2 149.44(12) . 1_455 ?
Cl1 Na1 Na2 130.21(8) . 1_455 ?
Ir1 Na1 Na2 155.92(7) . 1_455 ?
C14 O2 Ir2 116.7(2) . . ?
C14 O2 Na2 134.5(2) . . ?
Ir2 O2 Na2 108.73(12) . . ?
C9 N2 C13 120.3(3) . . ?
C9 N2 Ir2 125.7(3) . . ?
C13 N2 Ir2 113.8(2) . . ?
Na1 O6 H6A 109(5) . . ?
Na1 O6 H6B 125(5) . . ?
H6A O6 H6B 104(6) . . ?
Na1 O5 Na2 106.96(16) 1_655 . ?
Na1 O5 H5A 109(4) 1_655 . ?
Na2 O5 H5A 108(4) . . ?
Na1 O5 H5B 124(5) 1_655 . ?
Na2 O5 H5B 102(5) . . ?
H5A O5 H5B 105(6) . . ?
C6 O1 Ir1 116.6(2) . . ?
C6 O1 Na1 131.4(2) . . ?
Ir1 O1 Na1 111.53(14) . . ?
N2 C13 C12 120.4(4) . . ?
N2 C13 C14 116.4(3) . . ?
C12 C13 C14 123.2(4) . . ?
C12 C11 C10 119.1(4) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C9 C10 C11 119.0(4) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
O2 C14 C13 109.9(3) . . ?
O2 C14 C15 107.6(3) . . ?
C13 C14 C15 110.6(3) . . ?
O2 C14 C16 107.6(3) . . ?
C13 C14 C16 109.2(3) . . ?
C15 C14 C16 111.9(4) . . ?
O1 C6 C5 110.4(3) . . ?
O1 C6 C8 107.1(3) . . ?
C5 C6 C8 111.0(4) . . ?
O1 C6 C7 107.0(3) . . ?
C5 C6 C7 109.8(3) . . ?
C8 C6 C7 111.5(4) . . ?
N2 C9 C10 121.2(4) . . ?
N2 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Na2 O4 H4A 120(5) . . ?
Na2 O4 H4B 98(5) . . ?
H4A O4 H4B 101(6) . . ?
Na1 O7 H7D 117(5) . . ?
Na1 O7 H7E 120(4) . . ?
H7D O7 H7E 115(6) . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         1.785
_refine_diff_density_min         -2.046
_refine_diff_density_rms         0.177


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate, pentane'
####################################################################### 
# 
# 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_5iv
_database_code_depnum_ccdc_archive 'CCDC 1497508'
_audit_update_record             
;
2016-08-03 deposited with the CCDC.
2016-11-07 downloaded from the CCDC.
;
_audit_creation_date             2016-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            'Ir(pyalk)2Cl2, "yellow isomer"'
_chemical_name_systematic        
'cis-Cl, trans-O, cis-N-bis(2-{pyridin-2-yl}propan-2-olato)-dichloro-iridium(IV)'
_chemical_formula_moiety         '2(C16 H20 Cl2 Ir N2 O2), C H2 Cl2'
_chemical_formula_sum            'C33 H42 Cl6 Ir2 N4 O4'
_chemical_formula_weight         1155.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9782(4)
_cell_length_b                   15.0278(3)
_cell_length_c                   17.4463(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3927.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    68335
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      3.023
_shelx_estimated_absorpt_T_max   0.671
_shelx_estimated_absorpt_T_min   0.326
_exptl_absorpt_coefficient_mu    7.220
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private Communication'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.955
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_description       Block
_exptl_crystal_F_000             2224
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 'Rigaku R-AXIS RAPID, Rigaku R-AXIS RAPID imaging plate' 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            119682
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.023
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID imaging plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3872
_reflns_number_total             4503
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r12 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.948
_refine_diff_density_min         -2.064
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4503
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      0.905
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0662P)²+21.1695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1013
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Sof: Cl3(0.5) C50(0.5) H50A(0.5) H50B(0.5) Cl4(0.5)
 Fixed Uiso: H1(0.034) H3(0.051) H12(0.044) H9(0.033) H4(0.052) H10(0.044)
 H2(0.042) H11(0.048) H16A(0.053) H16B(0.053) H16C(0.053) H15A(0.058)
 H15B(0.058) H15C(0.058) H7A(0.068) H7B(0.068) H7C(0.068) H8A(0.074) H8B(0.074)
 H8C(0.074) H50A(0.131) H50B(0.131)
 Fixed X: H1(-0.046) H3(0.0635) H12(-0.2538) H9(0.0136) H4(0.1611) H10(-
 0.1114) H2(-0.0413) H11(-0.247) H16A(-0.1898) H16B(-0.1261) H16C(-0.0842)
 H15A(-0.1904) H15B(-0.19) H15C(-0.2544) H7A(0.1108) H7B(0.2082) H7C(0.1975)
 H8A(0.2927) H8B(0.308) H8C(0.2699) H50A(0.0146) H50B(-0.0578)
 Fixed Y: H1(0.0834) H3(0.2361) H12(0.1705) H9(0.3193) H4(0.2951) H10(0.3998)
 H2(0.1288) H11(0.3232) H16A(0.0131) H16B(-0.0609) H16C(0.0184) H15A(0.0728)
 H15B(-0.0276) H15C(0.0445) H7A(0.3782) H7B(0.3786) H7C(0.3819) H8A(0.2446)
 H8B(0.2435) H8C(0.157) H50A(0.4054) H50B(0.4771)
 Fixed Z: H1(0.5016) H3(0.6655) H12(0.2765) H9(0.3115) H4(0.5748) H10(0.2732)
 H2(0.6283) H11(0.2551) H16A(0.234) H16B(0.2707) H16C(0.2212) H15A(0.4331)
 H15B(0.4025) H15C(0.3638) H7A(0.4124) H7B(0.3746) H7C(0.4658) H8A(0.4824)
 H8B(0.3916) H8C(0.4339) H50A(0.5607) H50B(0.5846)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.05913(2) 0.12261(2) 0.35208(2) 0.02090(9) Uani 1 1 d . . . . .
N2 N -0.0464(3) 0.2011(3) 0.3199(3) 0.0255(9) Uani 1 1 d . . . . .
N1 N 0.0528(3) 0.1597(3) 0.4644(3) 0.0260(9) Uani 1 1 d . . . . .
C13 C -0.1244(3) 0.1572(4) 0.3107(3) 0.0268(10) Uani 1 1 d . . . . .
C1 C -0.0033(4) 0.1267(3) 0.5169(3) 0.0285(11) Uani 1 1 d . . . . .
H1 H -0.0460 0.0834 0.5016 0.034 Uiso 1 1 calc R U . . .
C3 C 0.0608(4) 0.2167(4) 0.6137(4) 0.0428(15) Uani 1 1 d . . . . .
H3 H 0.0635 0.2361 0.6655 0.051 Uiso 1 1 calc R U . . .
C12 C -0.1996(4) 0.2019(4) 0.2849(3) 0.0363(13) Uani 1 1 d . . . . .
H12 H -0.2538 0.1705 0.2765 0.044 Uiso 1 1 calc R U . . .
C9 C -0.0419(4) 0.2895(3) 0.3054(3) 0.0272(10) Uani 1 1 d . . . . .
H9 H 0.0136 0.3193 0.3115 0.033 Uiso 1 1 calc R U . . .
C4 C 0.1184(4) 0.2515(4) 0.5603(3) 0.0431(15) Uani 1 1 d . . . . .
H4 H 0.1611 0.2951 0.5748 0.052 Uiso 1 1 calc R U . . .
C5 C 0.1137(4) 0.2223(3) 0.4848(3) 0.0306(11) Uani 1 1 d . . . . .
C10 C -0.1153(4) 0.3376(4) 0.2820(3) 0.0367(13) Uani 1 1 d . . . . .
H10 H -0.1114 0.3998 0.2732 0.044 Uiso 1 1 calc R U . . .
C2 C -0.0011(4) 0.1534(4) 0.5919(3) 0.0346(12) Uani 1 1 d . . . . .
H2 H -0.0413 0.1288 0.6283 0.042 Uiso 1 1 calc R U . . .
C11 C -0.1952(4) 0.2920(4) 0.2715(4) 0.0397(13) Uani 1 1 d . . . . .
H11 H -0.2470 0.3232 0.2551 0.048 Uiso 1 1 calc R U . . .
Cl1 Cl 0.08129(8) 0.08824(8) 0.22282(7) 0.0283(3) Uani 1 1 d . . . . .
O2 O -0.0394(2) 0.0396(2) 0.3680(2) 0.0256(7) Uani 1 1 d . . . . .
C16 C -0.1314(4) 0.0023(4) 0.2575(3) 0.0352(12) Uani 1 1 d . . . . .
H16A H -0.1898 0.0131 0.2340 0.053 Uiso 1 1 calc R U . . .
H16B H -0.1261 -0.0609 0.2707 0.053 Uiso 1 1 calc R U . . .
H16C H -0.0842 0.0184 0.2212 0.053 Uiso 1 1 calc R U . . .
C14 C -0.1223(3) 0.0588(3) 0.3303(3) 0.0266(10) Uani 1 1 d . . . . .
C15 C -0.1959(3) 0.0350(4) 0.3876(4) 0.0387(13) Uani 1 1 d . . . . .
H15A H -0.1904 0.0728 0.4331 0.058 Uiso 1 1 calc R U . . .
H15B H -0.1900 -0.0276 0.4025 0.058 Uiso 1 1 calc R U . . .
H15C H -0.2544 0.0445 0.3638 0.058 Uiso 1 1 calc R U . . .
Cl2 Cl 0.16593(8) 0.01810(9) 0.38775(8) 0.0326(3) Uani 1 1 d . . . . .
O1 O 0.1397(2) 0.2255(2) 0.3492(2) 0.0278(8) Uani 1 1 d . . . . .
C6 C 0.1745(4) 0.2559(4) 0.4212(3) 0.0355(12) Uani 1 1 d . . . . .
C7 C 0.1726(5) 0.3578(4) 0.4182(4) 0.0456(16) Uani 1 1 d . . . . .
H7A H 0.1108 0.3782 0.4124 0.068 Uiso 1 1 calc R U . . .
H7B H 0.2082 0.3786 0.3746 0.068 Uiso 1 1 calc R U . . .
H7C H 0.1975 0.3819 0.4658 0.068 Uiso 1 1 calc R U . . .
C8 C 0.2699(4) 0.2223(5) 0.4334(4) 0.0490(16) Uani 1 1 d . . . . .
H8A H 0.2927 0.2446 0.4824 0.074 Uiso 1 1 calc R U . . .
H8B H 0.3080 0.2435 0.3916 0.074 Uiso 1 1 calc R U . . .
H8C H 0.2699 0.1570 0.4339 0.074 Uiso 1 1 calc R U . . .
Cl3 Cl -0.0748(12) 0.4337(11) 0.4705(10) 0.109(3) Uani 0.5 1 d D U P A -1
C50 C -0.0151(14) 0.4608(16) 0.5436(13) 0.109(3) Uani 0.5 1 d D U P A -1
H50A H 0.0146 0.4054 0.5607 0.131 Uiso 0.5 1 calc R U P A -1
H50B H -0.0578 0.4771 0.5846 0.131 Uiso 0.5 1 calc R U P A -1
Cl4 Cl 0.0613(12) 0.5373(11) 0.5441(9) 0.107(3) Uani 0.5 1 d D U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 N2 2.050(4) . ?
Ir1 N1 2.040(5) . ?
Ir1 Cl1 2.3372(13) . ?
Ir1 O2 1.952(3) . ?
Ir1 Cl2 2.3266(12) . ?
Ir1 O1 1.962(4) . ?
N2 C13 1.352(6) . ?
N2 C9 1.354(7) . ?
N1 C1 1.338(7) . ?
N1 C5 1.357(6) . ?
C13 C12 1.387(7) . ?
C13 C14 1.518(7) . ?
C1 C2 1.369(8) . ?
C3 C4 1.373(9) . ?
C3 C2 1.381(8) . ?
C12 C11 1.375(8) . ?
C9 C10 1.377(7) . ?
C4 C5 1.390(8) . ?
C5 C6 1.522(8) . ?
C10 C11 1.391(8) . ?
O2 C14 1.435(6) . ?
C16 C14 1.534(8) . ?
C14 C15 1.530(7) . ?
O1 C6 1.436(7) . ?
C6 C7 1.533(8) . ?
C6 C8 1.530(8) . ?
Cl3 C50 1.609(13) . ?
C50 Cl4 1.622(13) . ?

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
N2 Ir1 Cl1 88.44(13) . . ?
N2 Ir1 Cl2 172.54(13) . . ?
N1 Ir1 N2 93.98(17) . . ?
N1 Ir1 Cl1 173.76(12) . . ?
N1 Ir1 Cl2 87.68(12) . . ?
O2 Ir1 N2 79.84(17) . . ?
O2 Ir1 N1 90.13(16) . . ?
O2 Ir1 Cl1 95.96(12) . . ?
O2 Ir1 Cl2 92.90(11) . . ?
O2 Ir1 O1 166.42(16) . . ?
Cl2 Ir1 Cl1 90.64(5) . . ?
O1 Ir1 N2 90.77(16) . . ?
O1 Ir1 N1 80.69(16) . . ?
O1 Ir1 Cl1 93.54(11) . . ?
O1 Ir1 Cl2 96.68(12) . . ?
C13 N2 Ir1 114.7(4) . . ?
C9 N2 Ir1 125.3(4) . . ?
C9 N2 C13 119.9(5) . . ?
C1 N1 Ir1 125.8(4) . . ?
C1 N1 C5 120.0(5) . . ?
C5 N1 Ir1 114.2(4) . . ?
N2 C13 C12 120.3(5) . . ?
N2 C13 C14 115.5(4) . . ?
C12 C13 C14 124.2(5) . . ?
N1 C1 C2 122.0(5) . . ?
C4 C3 C2 119.8(6) . . ?
C11 C12 C13 119.6(5) . . ?
N2 C9 C10 122.1(5) . . ?
C3 C4 C5 119.4(5) . . ?
N1 C5 C4 120.1(5) . . ?
N1 C5 C6 116.2(5) . . ?
C4 C5 C6 123.7(5) . . ?
C9 C10 C11 117.8(5) . . ?
C1 C2 C3 118.8(5) . . ?
C12 C11 C10 120.2(5) . . ?
C14 O2 Ir1 117.4(3) . . ?
C13 C14 C16 110.6(5) . . ?
C13 C14 C15 111.1(4) . . ?
O2 C14 C13 108.5(4) . . ?
O2 C14 C16 110.3(4) . . ?
O2 C14 C15 106.0(4) . . ?
C15 C14 C16 110.3(4) . . ?
C6 O1 Ir1 116.9(3) . . ?
C5 C6 C7 110.2(5) . . ?
C5 C6 C8 110.3(5) . . ?
O1 C6 C5 108.3(4) . . ?
O1 C6 C7 106.4(5) . . ?
O1 C6 C8 110.8(5) . . ?
C7 C6 C8 110.7(5) . . ?
Cl3 C50 Cl4 125.2(16) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane, pentane'
