# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_maku052a_0m
_database_code_depnum_ccdc_archive 'CCDC 1571650'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
5,6,7-Trichloro-2-methoxy-8-hydroxyquinoline
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H6 Cl3 N O2'
_chemical_formula_sum            'C10 H6 Cl3 N O2'
_chemical_formula_weight         278.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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                   21.1155(9)
_cell_length_b                   4.9816(2)
_cell_length_c                   21.6442(8)
_cell_angle_alpha                90
_cell_angle_beta                 111.532(3)
_cell_angle_gamma                90
_cell_volume                     2117.84(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      3.221
_cell_measurement_theta_max      25.128

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.845
_shelx_estimated_absorpt_T_min   0.718
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_T_max  0.8865
_exptl_absorpt_correction_T_min  0.701699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0981 before and 0.0489 after correction.
The Ratio of minimum to maximum transmission is 0.7017.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_reflns_number            21650
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         25.246
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3794
_reflns_number_gt                2604
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0504P)²+0.8843P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3794
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.73961(17) 0.8108(7) 1.20375(15) 0.0176(7) Uani 1 1 d . . . . .
C1A C 0.76497(17) 1.1516(6) 1.04867(16) 0.0193(8) Uani 1 1 d . . . . .
C2 C 0.69115(18) 0.7826(7) 1.13823(15) 0.0202(8) Uani 1 1 d . . . . .
H2 H 0.697183 0.651579 1.108976 0.024 Uiso 1 1 calc R U . . .
C2A C 0.81169(17) 1.1609(7) 1.11528(15) 0.0198(8) Uani 1 1 d . . . . .
H2A H 0.805984 1.286330 1.145877 0.024 Uiso 1 1 calc R U . . .
C3 C 0.63592(17) 0.9469(7) 1.11815(15) 0.0191(8) Uani 1 1 d . . . . .
H3 H 0.603282 0.934721 1.074196 0.023 Uiso 1 1 calc R U . . .
C3A C 0.86472(17) 0.9865(7) 1.13433(15) 0.0193(8) Uani 1 1 d . . . . .
H3A H 0.896040 0.985660 1.178986 0.023 Uiso 1 1 calc R U . . .
C4 C 0.62725(16) 1.1389(6) 1.16380(15) 0.0171(7) Uani 1 1 d . . . . .
C4A C 0.87338(16) 0.8042(6) 1.08710(15) 0.0166(7) Uani 1 1 d . . . . .
C5 C 0.57182(17) 1.3181(7) 1.14903(15) 0.0178(7) Uani 1 1 d . . . . .
C5A C 0.92664(17) 0.6147(6) 1.10085(15) 0.0177(7) Uani 1 1 d . . . . .
C6 C 0.56690(16) 1.4941(7) 1.19583(15) 0.0194(8) Uani 1 1 d . . . . .
C6A C 0.93177(17) 0.4492(6) 1.05213(15) 0.0185(7) Uani 1 1 d . . . . .
C7 C 0.61773(16) 1.4948(6) 1.26020(15) 0.0169(7) Uani 1 1 d . . . . .
C7A C 0.88246(16) 0.4686(6) 0.98691(14) 0.0171(7) Uani 1 1 d . . . . .
C8 C 0.67257(17) 1.3244(6) 1.27615(15) 0.0158(7) Uani 1 1 d . . . . .
C8A C 0.83018(16) 0.6492(6) 0.97167(15) 0.0161(7) Uani 1 1 d . . . . .
C9 C 0.67832(17) 1.1444(6) 1.22781(15) 0.0151(7) Uani 1 1 d . . . . .
C9A C 0.82470(17) 0.8163(6) 1.02238(15) 0.0159(7) Uani 1 1 d . . . . .
C10 C 0.84595(18) 0.6773(8) 1.28444(16) 0.0268(9) Uani 1 1 d . . . . .
H10A H 0.882938 0.549390 1.290160 0.040 Uiso 1 1 calc R U . . .
H10B H 0.826689 0.645918 1.318678 0.040 Uiso 1 1 calc R U . . .
H10C H 0.863763 0.860798 1.288490 0.040 Uiso 1 1 calc R U . . .
C10A C 0.66150(19) 1.3097(8) 0.96714(16) 0.0306(9) Uani 1 1 d . . . . .
H10D H 0.682976 1.343051 0.934688 0.046 Uiso 1 1 calc R U . . .
H10E H 0.626097 1.444595 0.961823 0.046 Uiso 1 1 calc R U . . .
H10F H 0.641015 1.130351 0.959916 0.046 Uiso 1 1 calc R U . . .
N1 N 0.73459(13) 0.9815(5) 1.24761(12) 0.0169(6) Uani 1 1 d . . . . .
N1A N 0.77004(14) 0.9900(5) 1.00284(12) 0.0172(6) Uani 1 1 d . . . . .
O1 O 0.72055(11) 1.3262(4) 1.33825(10) 0.0193(5) Uani 1 1 d . . . . .
H1 H 0.750763 1.212488 1.340758 0.029 Uiso 1 1 calc R U . . .
O1A O 0.78387(11) 0.6661(4) 0.90872(10) 0.0199(5) Uani 1 1 d . . . . .
H1A H 0.754963 0.784603 0.906946 0.030 Uiso 1 1 calc R U . . .
O2 O 0.79359(12) 0.6417(5) 1.21958(11) 0.0226(6) Uani 1 1 d . . . . .
O2A O 0.71227(12) 1.3262(5) 1.03352(11) 0.0232(6) Uani 1 1 d . . . . .
Cl1 Cl 0.61206(4) 1.71091(16) 1.32053(4) 0.0219(2) Uani 1 1 d . . . . .
Cl1A Cl 0.88731(4) 0.26146(16) 0.92431(4) 0.0210(2) Uani 1 1 d . . . . .
Cl2 Cl 0.50058(4) 1.71988(18) 1.17713(4) 0.0265(2) Uani 1 1 d . . . . .
Cl2A Cl 0.99586(4) 0.21686(17) 1.06833(4) 0.0262(2) Uani 1 1 d . . . . .
Cl3 Cl 0.51035(5) 1.31775(19) 1.06926(4) 0.0297(2) Uani 1 1 d . . . . .
Cl3A Cl 0.98597(5) 0.59074(19) 1.18145(4) 0.0291(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.307(4) . ?
C1 O2 1.356(4) . ?
C1 C2 1.419(4) . ?
C1A N1A 1.312(4) . ?
C1A O2A 1.354(4) . ?
C1A C2A 1.418(4) . ?
C2 C3 1.359(5) . ?
C2A C3A 1.356(5) . ?
C3 C4 1.434(4) . ?
C3A C4A 1.429(4) . ?
C4 C9 1.409(4) . ?
C4 C5 1.412(5) . ?
C4A C9A 1.402(4) . ?
C4A C5A 1.414(5) . ?
C5 C6 1.372(4) . ?
C5 Cl3 1.738(3) . ?
C5A C6A 1.374(4) . ?
C5A Cl3A 1.738(3) . ?
C6 C7 1.413(4) . ?
C6 Cl2 1.725(3) . ?
C6A C7A 1.417(4) . ?
C6A Cl2A 1.716(3) . ?
C7 C8 1.374(4) . ?
C7 Cl1 1.730(3) . ?
C7A C8A 1.367(4) . ?
C7A Cl1A 1.736(3) . ?
C8 O1 1.354(4) . ?
C8 C9 1.416(4) . ?
C8A O1A 1.357(3) . ?
C8A C9A 1.416(4) . ?
C9 N1 1.371(4) . ?
C9A N1A 1.379(4) . ?
C10 O2 1.444(4) . ?
C10A O2A 1.446(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 O2 120.3(3) . . ?
N1 C1 C2 124.7(3) . . ?
O2 C1 C2 115.0(3) . . ?
N1A C1A O2A 119.9(3) . . ?
N1A C1A C2A 124.7(3) . . ?
O2A C1A C2A 115.4(3) . . ?
C3 C2 C1 118.7(3) . . ?
C3A C2A C1A 118.5(3) . . ?
C2 C3 C4 119.5(3) . . ?
C2A C3A C4A 119.9(3) . . ?
C9 C4 C5 118.8(3) . . ?
C9 C4 C3 116.4(3) . . ?
C5 C4 C3 124.8(3) . . ?
C9A C4A C5A 118.3(3) . . ?
C9A C4A C3A 116.6(3) . . ?
C5A C4A C3A 125.1(3) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 Cl3 120.2(3) . . ?
C4 C5 Cl3 118.6(2) . . ?
C6A C5A C4A 121.3(3) . . ?
C6A C5A Cl3A 119.9(3) . . ?
C4A C5A Cl3A 118.8(2) . . ?
C5 C6 C7 119.6(3) . . ?
C5 C6 Cl2 121.2(3) . . ?
C7 C6 Cl2 119.2(2) . . ?
C5A C6A C7A 119.2(3) . . ?
C5A C6A Cl2A 121.7(3) . . ?
C7A C6A Cl2A 119.0(2) . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 Cl1 118.7(2) . . ?
C6 C7 Cl1 120.5(3) . . ?
C8A C7A C6A 121.2(3) . . ?
C8A C7A Cl1A 118.5(2) . . ?
C6A C7A Cl1A 120.3(3) . . ?
O1 C8 C7 120.0(3) . . ?
O1 C8 C9 120.1(3) . . ?
C7 C8 C9 119.9(3) . . ?
O1A C8A C7A 120.2(3) . . ?
O1A C8A C9A 120.5(3) . . ?
C7A C8A C9A 119.2(3) . . ?
N1 C9 C4 123.9(3) . . ?
N1 C9 C8 116.3(3) . . ?
C4 C9 C8 119.8(3) . . ?
N1A C9A C4A 123.9(3) . . ?
N1A C9A C8A 115.4(3) . . ?
C4A C9A C8A 120.7(3) . . ?
C1 N1 C9 116.7(3) . . ?
C1A N1A C9A 116.4(3) . . ?
C1 O2 C10 116.2(3) . . ?
C1A O2A C10A 116.6(3) . . ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_maku90_0m
_database_code_depnum_ccdc_archive 'CCDC 1571652'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
Chlorido(7-chloro-8-hydroxyquinolinolato-5,6-dione-?N1,?O8)(?6-p-cymene)osmium(II)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 Cl2 N O3 Os, C H Cl3'
_chemical_formula_sum            'C20 H18 Cl5 N O3 Os'
_chemical_formula_weight         687.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'
Os Os -1.2165 7.6030 '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                   10.3571(6)
_cell_length_b                   21.0903(12)
_cell_length_c                   10.7050(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.136(3)
_cell_angle_gamma                90
_cell_volume                     2222.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      3.335
_cell_measurement_theta_max      25.112

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_F_000             1320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    6.363
_shelx_estimated_absorpt_T_min   0.251
_shelx_estimated_absorpt_T_max   0.429
_exptl_absorpt_correction_T_min  0.3294
_exptl_absorpt_correction_T_max  0.6359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0984 before and 0.0362 after correction.
The Ratio of minimum to maximum transmission is 0.5180.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_reflns_number            28099
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.931
_diffrn_reflns_theta_max         27.876
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5252
_reflns_number_gt                4664
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0251P)²+3.5168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5252
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0599
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6924(3) 0.18743(16) 0.2162(4) 0.0182(7) Uani 1 1 d . . . . .
H1 H 0.740411 0.157790 0.180514 0.022 Uiso 1 1 calc R U . . .
C2 C 0.7076(3) 0.25121(17) 0.1962(4) 0.0186(7) Uani 1 1 d . . . . .
H2 H 0.763572 0.264646 0.145715 0.022 Uiso 1 1 calc R U . . .
C3 C 0.6420(3) 0.29545(17) 0.2492(4) 0.0187(7) Uani 1 1 d . . . . .
H3 H 0.650725 0.339513 0.235228 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5624(3) 0.27375(17) 0.3236(3) 0.0171(7) Uani 1 1 d . . . . .
C5 C 0.4922(3) 0.31787(17) 0.3908(3) 0.0184(7) Uani 1 1 d . . . . .
C6 C 0.3936(3) 0.28879(16) 0.4587(4) 0.0184(7) Uani 1 1 d . . . . .
C7 C 0.3892(3) 0.22149(16) 0.4653(3) 0.0164(7) Uani 1 1 d . . . . .
C8 C 0.4619(3) 0.18109(15) 0.4101(3) 0.0148(7) Uani 1 1 d . . . . .
C9 C 0.5480(3) 0.20877(16) 0.3372(3) 0.0159(7) Uani 1 1 d . . . . .
C10 C 0.6294(4) 0.02688(16) 0.1647(4) 0.0190(7) Uani 1 1 d . . . . .
H10 H 0.678928 0.042608 0.110031 0.023 Uiso 1 1 calc R U . . .
C11 C 0.4858(4) 0.03909(16) 0.1290(4) 0.0202(7) Uani 1 1 d . . . . .
H11 H 0.441797 0.062671 0.051899 0.024 Uiso 1 1 calc R U . . .
C12 C 0.4107(3) 0.01594(16) 0.2088(4) 0.0195(7) Uani 1 1 d . . . . .
C13 C 0.2618(4) 0.03212(19) 0.1785(4) 0.0295(9) Uani 1 1 d . . . . .
H13A H 0.242618 0.072157 0.129704 0.044 Uiso 1 1 calc R U . . .
H13B H 0.239970 0.036455 0.260798 0.044 Uiso 1 1 calc R U . . .
H13C H 0.206469 -0.001751 0.125274 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4790(4) -0.02045(16) 0.3226(4) 0.0191(7) Uani 1 1 d . . . . .
H14 H 0.438(2) -0.0278(4) 0.380(3) 0.023 Uiso 1 1 calc R U . . .
C15 C 0.6194(4) -0.03179(17) 0.3571(4) 0.0197(7) Uani 1 1 d . . . . .
H15 H 0.662705 -0.055783 0.433822 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6988(4) -0.00785(16) 0.2788(4) 0.0190(7) Uani 1 1 d . . . . .
C17 C 0.8499(4) -0.02158(18) 0.3196(4) 0.0230(8) Uani 1 1 d . . . . .
H17 H 0.881337 -0.030064 0.416282 0.028 Uiso 1 1 calc R U . . .
C18 C 0.9341(4) 0.0331(2) 0.2930(5) 0.0340(10) Uani 1 1 d . . . . .
H18A H 0.912606 0.039122 0.197893 0.051 Uiso 1 1 calc R U . . .
H18B H 1.030935 0.023349 0.331234 0.051 Uiso 1 1 calc R U . . .
H18C H 0.912861 0.072015 0.332688 0.051 Uiso 1 1 calc R U . . .
C19 C 0.8718(4) -0.0822(2) 0.2495(5) 0.0326(10) Uani 1 1 d . . . . .
H19A H 0.817342 -0.116629 0.268547 0.049 Uiso 1 1 calc R U . . .
H19B H 0.968139 -0.093848 0.280630 0.049 Uiso 1 1 calc R U . . .
H19C H 0.843963 -0.074672 0.154430 0.049 Uiso 1 1 calc R U . . .
C20 C 1.0354(4) 0.30002(18) 0.5531(4) 0.0258(8) Uani 1 1 d . . . . .
H20 H 1.118007 0.300123 0.523581 0.031 Uiso 1 1 calc R U . . .
N1 N 0.6121(3) 0.16541(13) 0.2844(3) 0.0152(6) Uani 1 1 d . . . . .
O1 O 0.4582(2) 0.12040(11) 0.4154(2) 0.0172(5) Uani 1 1 d . . . . .
O2 O 0.5130(3) 0.37416(12) 0.3955(3) 0.0260(6) Uani 1 1 d . . . . .
O3 O 0.3295(3) 0.32580(12) 0.5059(3) 0.0248(6) Uani 1 1 d . . . . .
Cl1 Cl 0.75964(8) 0.09526(4) 0.53190(9) 0.02027(18) Uani 1 1 d . . . . .
Cl2 Cl 0.28704(8) 0.18835(4) 0.54900(9) 0.01984(18) Uani 1 1 d . . . . .
Cl3 Cl 0.92790(11) 0.36320(5) 0.47543(11) 0.0377(2) Uani 1 1 d . . . . .
Cl4 Cl 0.95124(9) 0.22675(5) 0.51111(10) 0.0278(2) Uani 1 1 d . . . . .
Cl5 Cl 1.08607(11) 0.31076(5) 0.72572(11) 0.0381(2) Uani 1 1 d . . . . .
Os1 Os 0.58451(2) 0.07040(2) 0.32987(2) 0.01477(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.348(4) . ?
C1 C2 1.379(5) . ?
C2 C3 1.377(5) . ?
C3 C4 1.390(5) . ?
C4 C9 1.391(5) . ?
C4 C5 1.496(5) . ?
C5 O2 1.205(4) . ?
C5 C6 1.552(5) . ?
C6 O3 1.230(4) . ?
C6 C7 1.423(5) . ?
C7 C8 1.385(5) . ?
C7 Cl2 1.733(3) . ?
C8 O1 1.282(4) . ?
C8 C9 1.476(5) . ?
C9 N1 1.352(4) . ?
C10 C16 1.414(5) . ?
C10 C11 1.438(5) . ?
C10 Os1 2.167(4) . ?
C11 C12 1.410(5) . ?
C11 Os1 2.176(4) . ?
C12 C14 1.427(5) . ?
C12 C13 1.512(5) . ?
C12 Os1 2.188(3) . ?
C14 C15 1.405(5) . ?
C14 Os1 2.195(3) . ?
C15 C16 1.437(5) . ?
C15 Os1 2.190(4) . ?
C16 C17 1.515(5) . ?
C16 Os1 2.197(3) . ?
C17 C18 1.526(5) . ?
C17 C19 1.534(5) . ?
C20 Cl4 1.763(4) . ?
C20 Cl3 1.769(4) . ?
C20 Cl5 1.771(4) . ?
N1 Os1 2.103(3) . ?
O1 Os1 2.100(2) . ?
Cl1 Os1 2.4085(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 122.7(3) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 C4 118.0(3) . . ?
C3 C4 C9 119.1(3) . . ?
C3 C4 C5 122.3(3) . . ?
C9 C4 C5 118.6(3) . . ?
O2 C5 C4 121.7(3) . . ?
O2 C5 C6 120.4(3) . . ?
C4 C5 C6 117.9(3) . . ?
O3 C6 C7 125.7(3) . . ?
O3 C6 C5 117.3(3) . . ?
C7 C6 C5 116.9(3) . . ?
C8 C7 C6 124.3(3) . . ?
C8 C7 Cl2 118.2(3) . . ?
C6 C7 Cl2 117.5(3) . . ?
O1 C8 C7 124.6(3) . . ?
O1 C8 C9 116.7(3) . . ?
C7 C8 C9 118.7(3) . . ?
N1 C9 C4 122.7(3) . . ?
N1 C9 C8 114.2(3) . . ?
C4 C9 C8 123.1(3) . . ?
C16 C10 C11 121.9(3) . . ?
C16 C10 Os1 72.3(2) . . ?
C11 C10 Os1 71.0(2) . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 Os1 71.6(2) . . ?
C10 C11 Os1 70.3(2) . . ?
C11 C12 C14 118.9(3) . . ?
C11 C12 C13 120.6(3) . . ?
C14 C12 C13 120.4(3) . . ?
C11 C12 Os1 70.7(2) . . ?
C14 C12 Os1 71.3(2) . . ?
C13 C12 Os1 127.2(3) . . ?
C15 C14 C12 120.9(3) . . ?
C15 C14 Os1 71.1(2) . . ?
C12 C14 Os1 70.72(19) . . ?
C14 C15 C16 121.4(3) . . ?
C14 C15 Os1 71.5(2) . . ?
C16 C15 Os1 71.2(2) . . ?
C10 C16 C15 117.2(3) . . ?
C10 C16 C17 123.4(3) . . ?
C15 C16 C17 119.5(3) . . ?
C10 C16 Os1 70.0(2) . . ?
C15 C16 Os1 70.60(19) . . ?
C17 C16 Os1 131.3(2) . . ?
C16 C17 C18 113.6(3) . . ?
C16 C17 C19 108.4(3) . . ?
C18 C17 C19 111.0(3) . . ?
Cl4 C20 Cl3 110.6(2) . . ?
Cl4 C20 Cl5 109.9(2) . . ?
Cl3 C20 Cl5 109.4(2) . . ?
C1 N1 C9 117.3(3) . . ?
C1 N1 Os1 127.2(2) . . ?
C9 N1 Os1 115.4(2) . . ?
C8 O1 Os1 116.8(2) . . ?
O1 Os1 N1 76.72(10) . . ?
O1 Os1 C10 152.83(12) . . ?
N1 Os1 C10 97.80(12) . . ?
O1 Os1 C11 114.76(11) . . ?
N1 Os1 C11 96.69(12) . . ?
C10 Os1 C11 38.68(13) . . ?
O1 Os1 C12 90.72(11) . . ?
N1 Os1 C12 120.63(12) . . ?
C10 Os1 C12 68.92(13) . . ?
C11 Os1 C12 37.70(14) . . ?
O1 Os1 C15 122.39(11) . . ?
N1 Os1 C15 160.08(12) . . ?
C10 Os1 C15 67.88(13) . . ?
C11 Os1 C15 80.80(13) . . ?
C12 Os1 C15 68.49(13) . . ?
O1 Os1 C14 94.77(11) . . ?
N1 Os1 C14 157.78(12) . . ?
C10 Os1 C14 80.34(14) . . ?
C11 Os1 C14 67.95(14) . . ?
C12 Os1 C14 38.00(13) . . ?
C15 Os1 C14 37.37(13) . . ?
O1 Os1 C16 160.58(11) . . ?
N1 Os1 C16 122.39(12) . . ?
C10 Os1 C16 37.79(13) . . ?
C11 Os1 C16 69.50(13) . . ?
C12 Os1 C16 82.30(13) . . ?
C15 Os1 C16 38.24(13) . . ?
C14 Os1 C16 68.68(13) . . ?
O1 Os1 Cl1 84.04(7) . . ?
N1 Os1 Cl1 83.20(8) . . ?
C10 Os1 Cl1 122.15(10) . . ?
C11 Os1 Cl1 160.76(9) . . ?
C12 Os1 Cl1 153.77(10) . . ?
C15 Os1 Cl1 92.74(10) . . ?
C14 Os1 Cl1 116.71(10) . . ?
C16 Os1 Cl1 94.22(10) . . ?

_refine_diff_density_max         1.967
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.133

####################################################################### 
# 
# 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_maku213_0m
_database_code_depnum_ccdc_archive 'CCDC 1571653'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
Chlorido(7-chloro-8-hydroxyquinolinolato-5,6-dione-?N1,?O8)(?5-pentamethylcyclopentadienyl)iridium(III) 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Cl2 Ir N O3'
_chemical_formula_sum            'C19 H18 Cl2 Ir N O3'
_chemical_formula_weight         571.44

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                   14.4492(8)
_cell_length_b                   7.3746(4)
_cell_length_c                   17.1873(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.400(2)
_cell_angle_gamma                90
_cell_volume                     1829.82(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      3.125
_cell_measurement_theta_max      25.226

_exptl_crystal_description       fragment
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.074
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    7.608
_shelx_estimated_absorpt_T_min   0.225
_shelx_estimated_absorpt_T_max   0.416
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1333 before and 0.0919 after correction.
The Ratio of minimum to maximum transmission is 0.5726.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_reflns_number            19988
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4198
_reflns_number_gt                3845
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0337P)²+0.7876P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4198
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0745
_refine_ls_wR_factor_gt          0.0730
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
C1 C 0.8819(3) 0.0347(6) 0.1909(3) 0.0202(9) Uani 1 1 d . . . . .
H1 H 0.857009 -0.013523 0.236777 0.024 Uiso 1 1 calc R U . . .
C2 C 0.9721(3) 0.1002(7) 0.1938(3) 0.0244(10) Uani 1 1 d . . . . .
H2 H 1.008960 0.093283 0.240797 0.029 Uiso 1 1 calc R U . . .
C3 C 1.0076(3) 0.1748(7) 0.1286(2) 0.0223(9) Uani 1 1 d . . . . .
H3 H 1.069316 0.219409 0.129600 0.027 Uiso 1 1 calc R U . . .
C4 C 0.9516(2) 0.1841(6) 0.0606(2) 0.0175(8) Uani 1 1 d . . . . .
C5 C 0.9837(3) 0.2684(6) -0.0122(2) 0.0202(9) Uani 1 1 d . . . . .
C6 C 0.9123(3) 0.2961(6) -0.0802(2) 0.0209(9) Uani 1 1 d . . . . .
C7 C 0.8257(3) 0.2041(6) -0.0751(2) 0.0154(8) Uani 1 1 d . . . . .
C8 C 0.7975(2) 0.1163(6) -0.0087(2) 0.0128(7) Uani 1 1 d . . . . .
C9 C 0.8629(2) 0.1138(6) 0.0608(2) 0.0127(7) Uani 1 1 d . . . . .
C18 C 0.7189(2) -0.3377(6) 0.1537(2) 0.0149(8) Uani 1 1 d . . . . .
C19 C 0.8117(3) -0.4168(6) 0.1765(3) 0.0216(10) Uani 1 1 d . . . . .
H19A H 0.804230 -0.544138 0.191320 0.032 Uiso 1 1 calc R U . . .
H19B H 0.839270 -0.348974 0.220682 0.032 Uiso 1 1 calc R U . . .
H19C H 0.852340 -0.409103 0.132353 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6741(2) -0.3449(5) 0.0783(2) 0.0135(8) Uani 1 1 d . . . . .
C11 C 0.7098(3) -0.4296(6) 0.0065(3) 0.0226(10) Uani 1 1 d . . . . .
H11A H 0.777640 -0.433356 0.010476 0.034 Uiso 1 1 calc R U . . .
H11B H 0.689700 -0.357732 -0.039102 0.034 Uiso 1 1 calc R U . . .
H1C H 0.685530 -0.553224 0.001019 0.034 Uiso 1 1 calc R U . . .
C12 C 0.5841(2) -0.2571(6) 0.0837(3) 0.0176(8) Uani 1 1 d . . . . .
C13 C 0.5137(3) -0.2420(7) 0.0172(3) 0.0315(12) Uani 1 1 d . . . . .
H13A H 0.481906 -0.358507 0.009792 0.047 Uiso 1 1 calc R U . . .
H13B H 0.544881 -0.209783 -0.030413 0.047 Uiso 1 1 calc R U . . .
H13C H 0.468437 -0.147998 0.028896 0.047 Uiso 1 1 calc R U . . .
C14 C 0.5747(3) -0.1969(6) 0.1621(3) 0.0206(9) Uani 1 1 d . . . . .
C15 C 0.4937(3) -0.0998(7) 0.1928(4) 0.0338(12) Uani 1 1 d . . . . .
H15A H 0.454986 -0.052392 0.149249 0.051 Uiso 1 1 calc R U . . .
H15B H 0.515430 0.000825 0.226015 0.051 Uiso 1 1 calc R U . . .
H15C H 0.457310 -0.183958 0.223352 0.051 Uiso 1 1 calc R U . . .
C16 C 0.6597(3) -0.2402(6) 0.2056(2) 0.0177(8) Uani 1 1 d . . . . .
C17 C 0.6772(4) -0.2119(7) 0.2916(3) 0.0311(11) Uani 1 1 d . . . . .
H17A H 0.643143 -0.104722 0.308250 0.047 Uiso 1 1 calc R U . . .
H17B H 0.743623 -0.193910 0.302724 0.047 Uiso 1 1 calc R U . . .
H17C H 0.656168 -0.318648 0.319872 0.047 Uiso 1 1 calc R U . . .
N1 N 0.8289(2) 0.0378(5) 0.12439(19) 0.0136(7) Uani 1 1 d . . . . .
O1 O 0.71923(19) 0.0430(4) -0.00075(17) 0.0155(6) Uani 1 1 d . . . . .
O3 O 0.9350(2) 0.3922(5) -0.13453(19) 0.0312(8) Uani 1 1 d . . . . .
O2 O 1.0630(2) 0.3147(6) -0.0186(2) 0.0371(9) Uani 1 1 d . . . . .
Cl1 Cl 0.64550(6) 0.23194(14) 0.14577(6) 0.0180(2) Uani 1 1 d . . . . .
Cl2 Cl 0.74874(7) 0.22154(15) -0.15457(6) 0.0224(2) Uani 1 1 d . . . . .
Ir Ir 0.69341(2) -0.06590(2) 0.11210(2) 0.01118(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.349(5) . ?
C1 C2 1.389(6) . ?
C2 C3 1.366(6) . ?
C3 C4 1.395(5) . ?
C4 C9 1.382(5) . ?
C4 C5 1.490(6) . ?
C5 O2 1.204(5) . ?
C5 C6 1.541(6) . ?
C6 O3 1.227(5) . ?
C6 C7 1.430(6) . ?
C7 C8 1.387(6) . ?
C7 Cl2 1.730(4) . ?
C8 O1 1.266(5) . ?
C8 C9 1.491(5) . ?
C9 N1 1.340(5) . ?
C18 C10 1.425(6) . ?
C18 C16 1.452(6) . ?
C18 C19 1.500(5) . ?
C18 Ir 2.154(4) . ?
C10 C12 1.459(5) . ?
C10 C11 1.494(6) . ?
C10 Ir 2.153(4) . ?
C12 C14 1.431(6) . ?
C12 C13 1.502(5) . ?
C12 Ir 2.158(4) . ?
C14 C16 1.447(5) . ?
C14 C15 1.488(6) . ?
C14 Ir 2.176(4) . ?
C16 C17 1.503(6) . ?
C16 Ir 2.130(4) . ?
N1 Ir 2.104(3) . ?
O1 Ir 2.146(3) . ?
Cl1 Ir 2.3816(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 121.6(4) . . ?
C3 C2 C1 119.6(4) . . ?
C2 C3 C4 118.8(4) . . ?
C9 C4 C3 119.0(4) . . ?
C9 C4 C5 118.7(3) . . ?
C3 C4 C5 122.3(3) . . ?
O2 C5 C4 121.7(4) . . ?
O2 C5 C6 120.2(4) . . ?
C4 C5 C6 118.1(3) . . ?
O3 C6 C7 125.7(4) . . ?
O3 C6 C5 117.5(4) . . ?
C7 C6 C5 116.8(4) . . ?
C8 C7 C6 124.1(3) . . ?
C8 C7 Cl2 118.9(3) . . ?
C6 C7 Cl2 116.8(3) . . ?
O1 C8 C7 125.6(3) . . ?
O1 C8 C9 116.6(3) . . ?
C7 C8 C9 117.8(3) . . ?
N1 C9 C4 122.0(3) . . ?
N1 C9 C8 114.6(3) . . ?
C4 C9 C8 123.4(4) . . ?
C10 C18 C16 108.7(3) . . ?
C10 C18 C19 126.1(4) . . ?
C16 C18 C19 125.1(4) . . ?
C10 C18 Ir 70.6(2) . . ?
C16 C18 Ir 69.3(2) . . ?
C19 C18 Ir 125.9(3) . . ?
C18 C10 C12 107.3(4) . . ?
C18 C10 C11 127.4(4) . . ?
C12 C10 C11 125.3(4) . . ?
C18 C10 Ir 70.7(2) . . ?
C12 C10 Ir 70.4(2) . . ?
C11 C10 Ir 125.2(3) . . ?
C14 C12 C10 108.5(3) . . ?
C14 C12 C13 127.3(4) . . ?
C10 C12 C13 124.1(4) . . ?
C14 C12 Ir 71.4(2) . . ?
C10 C12 Ir 70.1(2) . . ?
C13 C12 Ir 126.1(3) . . ?
C12 C14 C16 107.9(4) . . ?
C12 C14 C15 126.2(4) . . ?
C16 C14 C15 125.9(4) . . ?
C12 C14 Ir 70.0(2) . . ?
C16 C14 Ir 68.7(2) . . ?
C15 C14 Ir 124.8(3) . . ?
C14 C16 C18 107.5(3) . . ?
C14 C16 C17 125.6(4) . . ?
C18 C16 C17 126.5(4) . . ?
C14 C16 Ir 72.1(2) . . ?
C18 C16 Ir 71.1(2) . . ?
C17 C16 Ir 128.6(3) . . ?
C9 N1 C1 118.9(3) . . ?
C9 N1 Ir 116.2(2) . . ?
C1 N1 Ir 124.9(3) . . ?
C8 O1 Ir 116.6(2) . . ?
N1 Ir C16 112.62(14) . . ?
N1 Ir O1 76.02(11) . . ?
C16 Ir O1 164.05(14) . . ?
N1 Ir C10 118.96(14) . . ?
C16 Ir C10 66.17(16) . . ?
O1 Ir C10 98.00(13) . . ?
N1 Ir C18 99.20(13) . . ?
C16 Ir C18 39.60(16) . . ?
O1 Ir C18 127.90(13) . . ?
C10 Ir C18 38.64(15) . . ?
N1 Ir C12 158.33(15) . . ?
C16 Ir C12 65.69(15) . . ?
O1 Ir C12 101.15(14) . . ?
C10 Ir C12 39.55(14) . . ?
C18 Ir C12 65.18(14) . . ?
N1 Ir C14 150.11(15) . . ?
C16 Ir C14 39.24(15) . . ?
O1 Ir C14 133.83(13) . . ?
C10 Ir C14 65.60(16) . . ?
C18 Ir C14 65.32(15) . . ?
C12 Ir C14 38.54(17) . . ?
N1 Ir Cl1 85.35(10) . . ?
C16 Ir Cl1 107.16(12) . . ?
O1 Ir Cl1 86.43(8) . . ?
C10 Ir Cl1 155.67(10) . . ?
C18 Ir Cl1 145.55(11) . . ?
C12 Ir Cl1 116.12(11) . . ?
C14 Ir Cl1 94.10(12) . . ?

_refine_diff_density_max         1.146
_refine_diff_density_min         -1.719
_refine_diff_density_rms         0.197

####################################################################### 
# 
# 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_maku214_0m
_database_code_depnum_ccdc_archive 'CCDC 1571654'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
Chlorido(7-chloro-8-hydroxyquinolinolato-5,6-dione-?N1,?O8)(?5-pentamethylcyclopentadienyl)rhodium(III), 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 Cl2 N O3 Rh'
_chemical_formula_sum            'C19 H18 Cl2 N O3 Rh'
_chemical_formula_weight         482.15

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

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

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

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

_cell_length_a                   14.4730(7)
_cell_length_b                   7.3041(3)
_cell_length_c                   17.2691(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.709(3)
_cell_angle_gamma                90
_cell_volume                     1823.52(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      3.325
_cell_measurement_theta_max      25.116

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.249
_shelx_estimated_absorpt_T_min   0.788
_shelx_estimated_absorpt_T_max   0.885
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1106 before and 0.0909 after correction.
The Ratio of minimum to maximum transmission is 0.7751.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_reflns_number            21413
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.361
_diffrn_reflns_theta_max         27.752
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4268
_reflns_number_gt                3443
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0445P)²+5.1909P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4268
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1178
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
C9 C 0.6372(3) 0.1124(6) 0.9393(3) 0.0164(9) Uani 1 1 d . . . . .
C1 C 0.6187(3) 0.0377(6) 0.8100(3) 0.0208(9) Uani 1 1 d . . . . .
H1 H 0.643786 -0.009400 0.764155 0.025 Uiso 1 1 calc R U . . .
C2 C 0.5283(3) 0.1048(7) 0.8063(3) 0.0265(11) Uani 1 1 d . . . . .
H2 H 0.491938 0.100585 0.759093 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4926(3) 0.1770(7) 0.8719(3) 0.0249(10) Uani 1 1 d . . . . .
H3 H 0.430908 0.221382 0.871112 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5485(3) 0.1840(6) 0.9396(3) 0.0192(9) Uani 1 1 d . . . . .
C5 C 0.5159(3) 0.2678(6) 1.0117(3) 0.0234(10) Uani 1 1 d . . . . .
C6 C 0.5867(3) 0.2934(6) 1.0803(3) 0.0230(10) Uani 1 1 d . . . . .
C7 C 0.6728(3) 0.2023(6) 1.0757(3) 0.0196(9) Uani 1 1 d . . . . .
C8 C 0.7016(3) 0.1148(6) 1.0093(2) 0.0155(9) Uani 1 1 d . . . . .
C10 C 0.8248(3) -0.3448(6) 0.9239(3) 0.0179(9) Uani 1 1 d . . . . .
C11 C 0.7893(3) -0.4284(6) 0.9947(3) 0.0269(11) Uani 1 1 d . . . . .
H11A H 0.721633 -0.435102 0.989806 0.040 Uiso 1 1 calc R U . . .
H11B H 0.807917 -0.353377 1.039865 0.040 Uiso 1 1 calc R U . . .
H11C H 0.814790 -0.551967 1.001414 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9150(3) -0.2584(6) 0.9195(3) 0.0212(10) Uani 1 1 d . . . . .
C13 C 0.9842(4) -0.2401(7) 0.9865(4) 0.0400(14) Uani 1 1 d . . . . .
H13A H 1.010732 -0.360483 0.999153 0.060 Uiso 1 1 calc R U . . .
H13B H 0.953516 -0.191744 1.031527 0.060 Uiso 1 1 calc R U . . .
H13C H 1.033546 -0.156259 0.972456 0.060 Uiso 1 1 calc R U . . .
C14 C 0.9255(3) -0.1998(6) 0.8423(3) 0.0247(11) Uani 1 1 d . . . . .
C15 C 1.0077(4) -0.1061(7) 0.8109(4) 0.0416(15) Uani 1 1 d . . . . .
H15A H 1.047034 -0.057613 0.853894 0.062 Uiso 1 1 calc R U . . .
H15B H 0.986933 -0.005360 0.776895 0.062 Uiso 1 1 calc R U . . .
H15C H 1.043124 -0.194064 0.781308 0.062 Uiso 1 1 calc R U . . .
C16 C 0.8417(3) -0.2431(6) 0.7979(3) 0.0211(10) Uani 1 1 d . . . . .
C17 C 0.8254(4) -0.2107(7) 0.7129(3) 0.0380(13) Uani 1 1 d . . . . .
H17A H 0.868126 -0.116406 0.695872 0.057 Uiso 1 1 calc R U . . .
H17B H 0.761544 -0.169850 0.702407 0.057 Uiso 1 1 calc R U . . .
H17C H 0.835869 -0.324680 0.684667 0.057 Uiso 1 1 calc R U . . .
C18 C 0.7809(3) -0.3381(5) 0.8481(3) 0.0174(9) Uani 1 1 d . . . . .
C19 C 0.6892(3) -0.4167(6) 0.8254(3) 0.0254(10) Uani 1 1 d . . . . .
H19A H 0.695427 -0.548798 0.817157 0.038 Uiso 1 1 calc R U . . .
H19B H 0.665237 -0.358711 0.777424 0.038 Uiso 1 1 calc R U . . .
H19C H 0.646383 -0.394674 0.866718 0.038 Uiso 1 1 calc R U . . .
N1 N 0.6714(2) 0.0377(5) 0.8759(2) 0.0152(7) Uani 1 1 d . . . . .
O1 O 0.78071(19) 0.0417(4) 1.00242(17) 0.0182(6) Uani 1 1 d . . . . .
O3 O 0.5630(3) 0.3880(5) 1.1352(2) 0.0356(9) Uani 1 1 d . . . . .
O2 O 0.4365(2) 0.3134(6) 1.0179(2) 0.0387(9) Uani 1 1 d . . . . .
Cl1 Cl 0.85807(7) 0.23263(14) 0.85206(7) 0.0217(2) Uani 1 1 d . . . . .
Cl2 Cl 0.74940(8) 0.21699(16) 1.15578(7) 0.0268(3) Uani 1 1 d . . . . .
Rh1 Rh 0.80773(2) -0.06454(4) 0.88955(2) 0.01486(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 N1 1.339(6) . ?
C9 C4 1.386(6) . ?
C9 C8 1.491(6) . ?
C1 N1 1.340(5) . ?
C1 C2 1.397(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.372(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.390(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.486(6) . ?
C5 O2 1.206(5) . ?
C5 C6 1.541(6) . ?
C6 O3 1.234(5) . ?
C6 C7 1.418(6) . ?
C7 C8 1.394(6) . ?
C7 Cl2 1.734(5) . ?
C8 O1 1.274(5) . ?
C10 C18 1.428(6) . ?
C10 C12 1.456(6) . ?
C10 C11 1.480(6) . ?
C10 Rh1 2.143(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C14 1.415(7) . ?
C12 C13 1.499(6) . ?
C12 Rh1 2.146(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C16 1.440(6) . ?
C14 C15 1.497(7) . ?
C14 Rh1 2.163(4) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C18 1.443(6) . ?
C16 C17 1.494(7) . ?
C16 Rh1 2.127(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.481(6) . ?
C18 Rh1 2.151(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 Rh1 2.113(3) . ?
O1 Rh1 2.151(3) . ?
Cl1 Rh1 2.3887(11) . ?

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 C9 C4 122.3(4) . . ?
N1 C9 C8 115.2(3) . . ?
C4 C9 C8 122.5(4) . . ?
N1 C1 C2 122.2(4) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 118.8(4) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C9 C4 C3 119.1(4) . . ?
C9 C4 C5 119.3(4) . . ?
C3 C4 C5 121.6(4) . . ?
O2 C5 C4 122.0(4) . . ?
O2 C5 C6 120.1(4) . . ?
C4 C5 C6 117.9(4) . . ?
O3 C6 C7 125.6(4) . . ?
O3 C6 C5 117.3(4) . . ?
C7 C6 C5 117.0(4) . . ?
C8 C7 C6 124.0(4) . . ?
C8 C7 Cl2 118.7(3) . . ?
C6 C7 Cl2 117.2(3) . . ?
O1 C8 C7 125.0(4) . . ?
O1 C8 C9 116.7(4) . . ?
C7 C8 C9 118.2(4) . . ?
C18 C10 C12 107.4(4) . . ?
C18 C10 C11 127.9(4) . . ?
C12 C10 C11 124.7(4) . . ?
C18 C10 Rh1 70.9(2) . . ?
C12 C10 Rh1 70.3(2) . . ?
C11 C10 Rh1 125.6(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C14 C12 C10 108.5(4) . . ?
C14 C12 C13 127.0(4) . . ?
C10 C12 C13 124.5(5) . . ?
C14 C12 Rh1 71.5(2) . . ?
C10 C12 Rh1 70.0(2) . . ?
C13 C12 Rh1 125.2(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C16 108.1(4) . . ?
C12 C14 C15 127.0(5) . . ?
C16 C14 C15 124.9(5) . . ?
C12 C14 Rh1 70.2(2) . . ?
C16 C14 Rh1 69.0(2) . . ?
C15 C14 Rh1 125.6(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 C18 107.9(4) . . ?
C14 C16 C17 125.4(4) . . ?
C18 C16 C17 126.5(4) . . ?
C14 C16 Rh1 71.8(3) . . ?
C18 C16 Rh1 71.2(2) . . ?
C17 C16 Rh1 127.1(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C18 C16 108.1(4) . . ?
C10 C18 C19 125.7(4) . . ?
C16 C18 C19 126.2(4) . . ?
C10 C18 Rh1 70.3(2) . . ?
C16 C18 Rh1 69.4(2) . . ?
C19 C18 Rh1 126.4(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 N1 C1 118.5(4) . . ?
C9 N1 Rh1 115.6(3) . . ?
C1 N1 Rh1 125.8(3) . . ?
C8 O1 Rh1 116.0(3) . . ?
N1 Rh1 C16 112.42(16) . . ?
N1 Rh1 C10 117.60(15) . . ?
C16 Rh1 C10 65.96(17) . . ?
N1 Rh1 C12 157.10(16) . . ?
C16 Rh1 C12 65.48(17) . . ?
C10 Rh1 C12 39.68(16) . . ?
N1 Rh1 O1 76.38(12) . . ?
C16 Rh1 O1 162.60(15) . . ?
C10 Rh1 O1 96.73(14) . . ?
C12 Rh1 O1 100.36(15) . . ?
N1 Rh1 C18 97.94(14) . . ?
C16 Rh1 C18 39.42(17) . . ?
C10 Rh1 C18 38.86(17) . . ?
C12 Rh1 C18 65.46(16) . . ?
O1 Rh1 C18 126.77(14) . . ?
N1 Rh1 C14 150.24(17) . . ?
C16 Rh1 C14 39.21(17) . . ?
C10 Rh1 C14 65.51(17) . . ?
C12 Rh1 C14 38.34(18) . . ?
O1 Rh1 C14 133.37(16) . . ?
C18 Rh1 C14 65.39(16) . . ?
N1 Rh1 Cl1 86.79(10) . . ?
C16 Rh1 Cl1 105.74(13) . . ?
C10 Rh1 Cl1 155.60(12) . . ?
C12 Rh1 Cl1 116.00(13) . . ?
O1 Rh1 Cl1 89.35(8) . . ?
C18 Rh1 Cl1 143.75(12) . . ?
C14 Rh1 Cl1 93.26(13) . . ?

_refine_diff_density_max         1.738
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.147

####################################################################### 
# 
# 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_maku059_0m_2
_database_code_depnum_ccdc_archive 'CCDC 1571651'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
;
Chlorido(7-chloro-8-hydroxyquinolinolato-5,6-dione-?N1,?O8)(?6-p-cymene)ruthenium(II)
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 Cl2 N O3 Ru, C H2 Cl2'
_chemical_formula_sum            'C20 H19 Cl4 N O3 Ru'
_chemical_formula_weight         564.36

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'
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'
Ru Ru -1.2594 0.8363 '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                   10.6343(5)
_cell_length_b                   21.1270(9)
_cell_length_c                   19.5934(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.782(3)
_cell_angle_gamma                90
_cell_volume                     4324.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      3.215
_cell_measurement_theta_max      25.112

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             2257
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.242
_shelx_estimated_absorpt_T_min   0.670
_shelx_estimated_absorpt_T_max   0.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6512
_exptl_absorpt_correction_T_max  0.8623
_exptl_absorpt_process_details   
;
SADABS-2004/1 (Bruker,2004) was used for absorption correction.
R(int) was 0.0627 before and 0.0418 after correction.
The Ratio of minimum to maximum transmission is 0.7552.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_reflns_number            47848
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.431
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8462
_reflns_number_gt                6730
_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       'APEX2 (Bruker, 2008)'
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_solution    'SHELXS-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0234P)²+37.6563P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8462
_refine_ls_number_parameters     549
_refine_ls_number_restraints     196
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.182
_refine_ls_restrained_S_all      1.180
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1237(6) 0.3216(3) 0.6551(3) 0.0255(13) Uani 1 1 d . U . . .
H1 H -0.181926 0.351020 0.629608 0.031 Uiso 1 1 calc R U . . .
C2 C -0.1494(6) 0.2581(3) 0.6458(3) 0.0280(14) Uani 1 1 d . U . . .
H2 H -0.224956 0.244348 0.615595 0.034 Uiso 1 1 calc R U . . .
C3 C -0.0635(6) 0.2144(3) 0.6809(3) 0.0234(13) Uani 1 1 d . U . . .
H3 H -0.079064 0.170232 0.675260 0.028 Uiso 1 1 calc R U . . .
C4 C 0.0451(6) 0.2365(3) 0.7243(3) 0.0202(12) Uani 1 1 d . U . . .
C5 C 0.1460(6) 0.1940(3) 0.7617(3) 0.0247(13) Uani 1 1 d . U . . .
C8 C 0.1741(6) 0.3296(3) 0.7800(3) 0.0214(12) Uani 1 1 d . U . . .
C9 C 0.0635(6) 0.3020(3) 0.7332(3) 0.0239(13) Uani 1 1 d . U . . .
C10 C -0.1140(6) 0.4718(3) 0.7633(3) 0.0227(12) Uani 1 1 d . U . . .
H10 H -0.168441 0.448754 0.787584 0.027 Uiso 1 1 calc R U . . .
C11 C 0.0026(6) 0.4971(3) 0.7998(3) 0.0256(13) Uani 1 1 d . U . . .
C12 C 0.0476(7) 0.4846(4) 0.8761(4) 0.0373(16) Uani 1 1 d . . . . .
H12A H 0.140124 0.476896 0.885255 0.056 Uiso 1 1 calc R U . . .
H12B H 0.003394 0.447283 0.889736 0.056 Uiso 1 1 calc R U . . .
H12C H 0.028606 0.521351 0.902886 0.056 Uiso 1 1 calc R U . . .
C13 C 0.0813(6) 0.5317(3) 0.7617(3) 0.0232(13) Uani 1 1 d . U . . .
H13 H 0.159462 0.549496 0.785365 0.028 Uiso 1 1 calc R U . . .
C15 C -0.0729(6) 0.5144(3) 0.6515(3) 0.0235(13) Uani 1 1 d . U . . .
C16 C -0.1083(6) 0.5248(3) 0.5744(3) 0.0264(13) Uani 1 1 d . . . . .
H16 H -0.027497 0.534061 0.557094 0.032 Uiso 1 1 calc R U . . .
C17 C -0.1714(7) 0.4687(3) 0.5338(4) 0.0382(17) Uani 1 1 d . . . . .
H17A H -0.184825 0.478092 0.483950 0.057 Uiso 1 1 calc R U . . .
H17B H -0.253998 0.460235 0.547213 0.057 Uiso 1 1 calc R U . . .
H17C H -0.116109 0.431440 0.543828 0.057 Uiso 1 1 calc R U . . .
C18 C -0.1932(8) 0.5845(4) 0.5618(4) 0.0421(18) Uani 1 1 d . . . . .
H18A H -0.209377 0.595120 0.512275 0.063 Uiso 1 1 calc R U . . .
H18B H -0.149336 0.619951 0.588581 0.063 Uiso 1 1 calc R U . . .
H18C H -0.274712 0.576433 0.576716 0.063 Uiso 1 1 calc R U . . .
C19 C -0.1499(6) 0.4809(3) 0.6898(3) 0.0221(12) Uani 1 1 d . U . . .
H19 H -0.228641 0.463694 0.666259 0.027 Uiso 1 1 calc R U . . .
C20 C 0.3748(6) 0.2010(3) 0.6608(3) 0.0238(13) Uani 1 1 d . U . . .
H20 H 0.316103 0.171780 0.635334 0.029 Uiso 1 1 calc R U . . .
C21 C 0.3460(6) 0.2653(3) 0.6561(3) 0.0274(14) Uani 1 1 d . U . . .
H21 H 0.266878 0.279574 0.629701 0.033 Uiso 1 1 calc R U . . .
C22 C 0.4340(6) 0.3080(3) 0.6901(3) 0.0271(14) Uani 1 1 d . U . . .
H22 H 0.417199 0.352126 0.686726 0.033 Uiso 1 1 calc R U . . .
C24 C 0.6487(6) 0.3287(3) 0.7645(3) 0.0256(13) Uani 1 1 d . U . . .
C23 C 0.5467(6) 0.2856(3) 0.7293(3) 0.0241(13) Uani 1 1 d . U . . .
C27 C 0.6839(5) 0.1923(3) 0.7773(3) 0.0213(12) Uani 1 1 d . U . . .
C30 C 0.3905(6) 0.0514(3) 0.7624(3) 0.0230(13) Uani 1 1 d . U . . .
H30 H 0.334539 0.074227 0.786015 0.028 Uiso 1 1 calc R U . . .
C31 C 0.5070(6) 0.0281(3) 0.7995(3) 0.0242(13) Uani 1 1 d . U . . .
C32 C 0.5509(7) 0.0434(3) 0.8751(3) 0.0349(16) Uani 1 1 d . . . . .
H32A H 0.642200 0.054023 0.883633 0.052 Uiso 1 1 calc R U . . .
H32B H 0.537197 0.006570 0.903283 0.052 Uiso 1 1 calc R U . . .
H32C H 0.502015 0.079442 0.887664 0.052 Uiso 1 1 calc R U . . .
C33 C 0.5868(6) -0.0076(3) 0.7626(3) 0.0242(13) Uani 1 1 d . U . . .
H33 H 0.665811 -0.023853 0.787074 0.029 Uiso 1 1 calc R U . . .
C35 C 0.4340(6) 0.0069(3) 0.6522(3) 0.0248(13) Uani 1 1 d . U . . .
C36 C 0.3999(6) -0.0055(3) 0.5750(3) 0.0325(15) Uani 1 1 d . . . . .
H36 H 0.481527 -0.013693 0.558158 0.039 Uiso 1 1 calc R U . . .
C37 C 0.3192(8) -0.0660(4) 0.5630(4) 0.0458(19) Uani 1 1 d . . . . .
H37A H 0.303466 -0.076829 0.513494 0.069 Uiso 1 1 calc R U . . .
H37B H 0.237345 -0.059156 0.577950 0.069 Uiso 1 1 calc R U . . .
H37C H 0.365297 -0.100798 0.589889 0.069 Uiso 1 1 calc R U . . .
C38 C 0.3337(8) 0.0502(4) 0.5336(4) 0.0454(19) Uani 1 1 d . . . . .
H38A H 0.319324 0.040218 0.483912 0.068 Uiso 1 1 calc R U . . .
H38B H 0.387932 0.087917 0.542722 0.068 Uiso 1 1 calc R U . . .
H38C H 0.251387 0.058289 0.547579 0.068 Uiso 1 1 calc R U . . .
C39 C 0.3560(6) 0.0410(3) 0.6896(3) 0.0251(13) Uani 1 1 d . U . . .
H39 H 0.277315 0.057810 0.665355 0.030 Uiso 1 1 calc R U . . .
N1 N -0.0206(5) 0.3443(2) 0.6985(3) 0.0235(11) Uani 1 1 d . U . . .
N2 N 0.4831(5) 0.1788(2) 0.7004(3) 0.0211(10) Uani 1 1 d . U . . .
O1 O 0.1813(4) 0.39024(19) 0.7814(2) 0.0249(9) Uani 1 1 d . . . . .
O2 O 0.1431(4) 0.1370(2) 0.7505(3) 0.0345(11) Uani 1 1 d . . . . .
O4 O 0.6910(4) 0.13148(18) 0.7770(2) 0.0229(9) Uani 1 1 d . . . . .
O5 O 0.6424(4) 0.38529(19) 0.7553(3) 0.0333(11) Uani 1 1 d . . . . .
O3 O 0.3415(4) 0.1863(2) 0.8437(2) 0.0333(11) Uani 1 1 d . . . . .
O6 O 0.8499(4) 0.3361(2) 0.8417(2) 0.0329(11) Uani 1 1 d . . . . .
Cl1 Cl 0.15971(14) 0.41298(7) 0.62394(8) 0.0248(3) Uani 1 1 d . . . . .
Cl2 Cl 0.65641(15) 0.11063(8) 0.61962(8) 0.0301(3) Uani 1 1 d . . . . .
Cl3 Cl 0.39280(15) 0.32369(7) 0.87420(9) 0.0318(4) Uani 1 1 d . . . . .
Cl4 Cl 0.90792(14) 0.19855(7) 0.86622(8) 0.0282(3) Uani 1 1 d . . . . .
Ru1 Ru 0.03931(4) 0.43898(2) 0.71270(3) 0.01973(13) Uani 1 1 d . . . . .
Ru2 Ru 0.54330(4) 0.08387(2) 0.71124(3) 0.02017(13) Uani 1 1 d . . . . .
C14 C 0.0452(6) 0.5399(3) 0.6899(3) 0.0214(12) Uani 1 1 d . U . . .
H14 H 0.099917 0.562886 0.665759 0.026 Uiso 1 1 calc R U . . .
C34 C 0.5516(6) -0.0192(3) 0.6913(3) 0.0275(14) Uani 1 1 d . U . . .
H34 H 0.605204 -0.044275 0.668440 0.033 Uiso 1 1 calc R U . . .
C7 C 0.2638(6) 0.2900(3) 0.8191(3) 0.0260(13) Uani 1 1 d . U . . .
C6 C 0.2599(6) 0.2222(3) 0.8130(3) 0.0230(13) Uani 1 1 d . U . . .
C26 C 0.7740(6) 0.2319(3) 0.8145(3) 0.0210(12) Uani 1 1 d . U . . .
C25 C 0.7677(6) 0.2993(3) 0.8116(3) 0.0256(13) Uani 1 1 d . U . . .
C28 C 0.5677(5) 0.2207(2) 0.7345(3) 0.0180(12) Uani 1 1 d . U . . .
C40 C 0.0992(9) 0.3222(4) 0.9642(4) 0.0387(19) Uani 0.877(4) 1 d D . P A 1
H40A H 0.030101 0.315955 0.923276 0.046 Uiso 0.877(4) 1 calc R U P A 1
H40B H 0.160661 0.353138 0.951371 0.046 Uiso 0.877(4) 1 calc R U P A 1
Cl5 Cl 0.0331(4) 0.35295(17) 1.03318(19) 0.0658(8) Uani 0.877(4) 1 d D . P A 1
Cl6 Cl 0.1780(2) 0.24985(12) 0.98574(12) 0.0514(7) Uani 0.877(4) 1 d D . P A 1
C40A C 0.020(3) 0.302(2) 0.994(3) 0.0387(19) Uani 0.123(4) 1 d D . P A 2
H40C H -0.004091 0.262387 1.014891 0.046 Uiso 0.123(4) 1 calc R U P A 2
H40D H -0.044567 0.311391 0.952245 0.046 Uiso 0.123(4) 1 calc R U P A 2
Cl5A Cl 0.020(3) 0.3642(14) 1.0546(16) 0.0658(8) Uani 0.123(4) 1 d D . P A 2
Cl6A Cl 0.1710(17) 0.2936(10) 0.9716(9) 0.0514(7) Uani 0.123(4) 1 d D . P A 2
C41 C 0.5248(9) 0.2994(5) 0.4968(5) 0.048(2) Uani 0.841(5) 1 d D . P B 3
H41A H 0.454970 0.303046 0.455776 0.057 Uiso 0.841(5) 1 calc R U P B 3
H41B H 0.507896 0.261531 0.523400 0.057 Uiso 0.841(5) 1 calc R U P B 3
Cl7 Cl 0.5249(3) 0.36643(16) 0.54874(16) 0.0517(7) Uani 0.841(5) 1 d D . P B 3
Cl8 Cl 0.6709(3) 0.28961(18) 0.46871(14) 0.0640(9) Uani 0.841(5) 1 d D . P B 3
C41A C 0.541(3) 0.2693(16) 0.501(3) 0.048(2) Uani 0.159(5) 1 d D . P B 4
H41C H 0.469907 0.268042 0.460794 0.057 Uiso 0.159(5) 1 calc R U P B 4
H41D H 0.518438 0.240316 0.536948 0.057 Uiso 0.159(5) 1 calc R U P B 4
Cl7A Cl 0.5519(19) 0.3459(9) 0.5351(10) 0.0517(7) Uani 0.159(5) 1 d D . P B 4
Cl8A Cl 0.6794(15) 0.2404(10) 0.4756(8) 0.0640(9) Uani 0.159(5) 1 d D . P B 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.344(8) . ?
C1 C2 1.374(9) . ?
C2 C3 1.389(8) . ?
C3 C4 1.381(8) . ?
C4 C9 1.404(8) . ?
C4 C5 1.482(8) . ?
C5 O2 1.225(7) . ?
C5 C6 1.541(8) . ?
C8 O1 1.283(7) . ?
C8 C7 1.387(8) . ?
C8 C9 1.470(8) . ?
C9 N1 1.354(8) . ?
C10 C11 1.415(8) . ?
C10 C19 1.432(8) . ?
C10 Ru1 2.174(6) . ?
C11 C13 1.424(9) . ?
C11 C12 1.504(9) . ?
C11 Ru1 2.197(6) . ?
C13 C14 1.398(8) . ?
C13 Ru1 2.191(6) . ?
C15 C19 1.402(8) . ?
C15 C14 1.442(8) . ?
C15 C16 1.503(9) . ?
C15 Ru1 2.205(6) . ?
C16 C17 1.513(9) . ?
C16 C18 1.545(9) . ?
C19 Ru1 2.167(6) . ?
C20 N2 1.347(7) . ?
C20 C21 1.393(9) . ?
C21 C22 1.378(9) . ?
C22 C23 1.380(8) . ?
C24 O5 1.209(7) . ?
C24 C23 1.483(8) . ?
C24 C25 1.551(8) . ?
C23 C28 1.392(8) . ?
C27 O4 1.287(7) . ?
C27 C26 1.374(8) . ?
C27 C28 1.484(8) . ?
C30 C31 1.404(8) . ?
C30 C39 1.423(9) . ?
C30 Ru2 2.174(6) . ?
C31 C33 1.429(9) . ?
C31 C32 1.502(9) . ?
C31 Ru2 2.187(6) . ?
C33 C34 1.398(9) . ?
C33 Ru2 2.188(6) . ?
C35 C39 1.405(9) . ?
C35 C34 1.448(8) . ?
C35 C36 1.510(9) . ?
C35 Ru2 2.199(6) . ?
C36 C38 1.525(10) . ?
C36 C37 1.533(10) . ?
C39 Ru2 2.157(6) . ?
N1 Ru1 2.102(5) . ?
N2 C28 1.346(7) . ?
N2 Ru2 2.103(5) . ?
O1 Ru1 2.096(4) . ?
O4 Ru2 2.094(4) . ?
O3 C6 1.222(7) . ?
O6 C25 1.234(7) . ?
Cl1 Ru1 2.4080(16) . ?
Cl2 Ru2 2.4077(16) . ?
Cl3 C7 1.733(6) . ?
Cl4 C26 1.735(6) . ?
Ru1 C14 2.181(6) . ?
Ru2 C34 2.216(6) . ?
C7 C6 1.437(9) . ?
C26 C25 1.426(8) . ?
C40 Cl6 1.756(8) . ?
C40 Cl5 1.760(9) . ?
C40A Cl6A 1.755(13) . ?
C40A Cl5A 1.757(13) . ?
C41 Cl7 1.744(11) . ?
C41 Cl8 1.754(10) . ?
C41A Cl7A 1.743(15) . ?
C41A Cl8A 1.753(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.4(6) . . ?
C1 C2 C3 119.2(6) . . ?
C4 C3 C2 118.5(5) . . ?
C3 C4 C9 119.4(5) . . ?
C3 C4 C5 123.0(5) . . ?
C9 C4 C5 117.6(5) . . ?
O2 C5 C4 121.0(6) . . ?
O2 C5 C6 119.2(5) . . ?
C4 C5 C6 119.8(5) . . ?
O1 C8 C7 123.9(5) . . ?
O1 C8 C9 116.6(5) . . ?
C7 C8 C9 119.5(5) . . ?
N1 C9 C4 121.7(5) . . ?
N1 C9 C8 115.3(5) . . ?
C4 C9 C8 123.0(5) . . ?
C11 C10 C19 120.1(6) . . ?
C11 C10 Ru1 72.0(4) . . ?
C19 C10 Ru1 70.5(3) . . ?
C10 C11 C13 118.3(6) . . ?
C10 C11 C12 121.4(6) . . ?
C13 C11 C12 120.2(6) . . ?
C10 C11 Ru1 70.2(3) . . ?
C13 C11 Ru1 70.8(3) . . ?
C12 C11 Ru1 127.1(4) . . ?
C14 C13 C11 120.9(5) . . ?
C14 C13 Ru1 71.0(3) . . ?
C11 C13 Ru1 71.3(3) . . ?
C19 C15 C14 116.5(5) . . ?
C19 C15 C16 123.4(5) . . ?
C14 C15 C16 120.0(5) . . ?
C19 C15 Ru1 69.8(3) . . ?
C14 C15 Ru1 69.9(3) . . ?
C16 C15 Ru1 131.4(4) . . ?
C15 C16 C17 114.6(5) . . ?
C15 C16 C18 108.0(5) . . ?
C17 C16 C18 111.6(6) . . ?
C15 C19 C10 122.3(5) . . ?
C15 C19 Ru1 72.8(3) . . ?
C10 C19 Ru1 71.0(3) . . ?
N2 C20 C21 122.2(6) . . ?
C22 C21 C20 119.0(6) . . ?
C21 C22 C23 119.1(6) . . ?
O5 C24 C23 121.5(6) . . ?
O5 C24 C25 120.1(6) . . ?
C23 C24 C25 118.4(5) . . ?
C22 C23 C28 119.3(6) . . ?
C22 C23 C24 122.2(6) . . ?
C28 C23 C24 118.5(5) . . ?
O4 C27 C26 125.0(5) . . ?
O4 C27 C28 116.3(5) . . ?
C26 C27 C28 118.6(5) . . ?
C31 C30 C39 120.2(6) . . ?
C31 C30 Ru2 71.7(4) . . ?
C39 C30 Ru2 70.2(3) . . ?
C30 C31 C33 118.3(6) . . ?
C30 C31 C32 121.1(6) . . ?
C33 C31 C32 120.5(6) . . ?
C30 C31 Ru2 70.7(3) . . ?
C33 C31 Ru2 71.0(3) . . ?
C32 C31 Ru2 126.5(4) . . ?
C34 C33 C31 121.6(6) . . ?
C34 C33 Ru2 72.6(4) . . ?
C31 C33 Ru2 70.9(3) . . ?
C39 C35 C34 117.1(6) . . ?
C39 C35 C36 123.8(6) . . ?
C34 C35 C36 119.1(6) . . ?
C39 C35 Ru2 69.6(4) . . ?
C34 C35 Ru2 71.5(3) . . ?
C36 C35 Ru2 131.2(4) . . ?
C35 C36 C38 113.6(6) . . ?
C35 C36 C37 108.7(6) . . ?
C38 C36 C37 111.9(6) . . ?
C35 C39 C30 122.4(6) . . ?
C35 C39 Ru2 72.8(4) . . ?
C30 C39 Ru2 71.5(3) . . ?
C1 N1 C9 117.8(5) . . ?
C1 N1 Ru1 127.9(4) . . ?
C9 N1 Ru1 114.0(4) . . ?
C28 N2 C20 118.4(5) . . ?
C28 N2 Ru2 114.5(4) . . ?
C20 N2 Ru2 127.0(4) . . ?
C8 O1 Ru1 116.3(4) . . ?
C27 O4 Ru2 116.4(3) . . ?
O1 Ru1 N1 77.38(17) . . ?
O1 Ru1 C19 149.7(2) . . ?
N1 Ru1 C19 96.6(2) . . ?
O1 Ru1 C10 112.0(2) . . ?
N1 Ru1 C10 97.4(2) . . ?
C19 Ru1 C10 38.5(2) . . ?
O1 Ru1 C14 124.54(19) . . ?
N1 Ru1 C14 157.3(2) . . ?
C19 Ru1 C14 67.6(2) . . ?
C10 Ru1 C14 80.4(2) . . ?
O1 Ru1 C13 95.42(19) . . ?
N1 Ru1 C13 160.2(2) . . ?
C19 Ru1 C13 80.2(2) . . ?
C10 Ru1 C13 67.9(2) . . ?
C14 Ru1 C13 37.3(2) . . ?
O1 Ru1 C11 89.2(2) . . ?
N1 Ru1 C11 122.8(2) . . ?
C19 Ru1 C11 68.8(2) . . ?
C10 Ru1 C11 37.8(2) . . ?
C14 Ru1 C11 68.2(2) . . ?
C13 Ru1 C11 37.9(2) . . ?
O1 Ru1 C15 162.9(2) . . ?
N1 Ru1 C15 119.7(2) . . ?
C19 Ru1 C15 37.4(2) . . ?
C10 Ru1 C15 69.0(2) . . ?
C14 Ru1 C15 38.4(2) . . ?
C13 Ru1 C15 68.8(2) . . ?
C11 Ru1 C15 82.1(2) . . ?
O1 Ru1 Cl1 86.31(12) . . ?
N1 Ru1 Cl1 82.90(14) . . ?
C19 Ru1 Cl1 122.85(16) . . ?
C10 Ru1 Cl1 161.36(16) . . ?
C14 Ru1 Cl1 92.05(16) . . ?
C13 Ru1 Cl1 115.35(17) . . ?
C11 Ru1 Cl1 152.21(17) . . ?
C15 Ru1 Cl1 94.50(17) . . ?
O4 Ru2 N2 77.47(17) . . ?
O4 Ru2 C39 151.9(2) . . ?
N2 Ru2 C39 97.3(2) . . ?
O4 Ru2 C30 114.0(2) . . ?
N2 Ru2 C30 96.2(2) . . ?
C39 Ru2 C30 38.3(2) . . ?
O4 Ru2 C31 89.73(19) . . ?
N2 Ru2 C31 119.9(2) . . ?
C39 Ru2 C31 68.7(2) . . ?
C30 Ru2 C31 37.5(2) . . ?
O4 Ru2 C33 94.10(19) . . ?
N2 Ru2 C33 157.3(2) . . ?
C39 Ru2 C33 80.1(2) . . ?
C30 Ru2 C33 67.8(2) . . ?
C31 Ru2 C33 38.1(2) . . ?
O4 Ru2 C35 160.30(19) . . ?
N2 Ru2 C35 122.1(2) . . ?
C39 Ru2 C35 37.6(2) . . ?
C30 Ru2 C35 69.0(2) . . ?
C31 Ru2 C35 82.1(2) . . ?
C33 Ru2 C35 68.5(2) . . ?
O4 Ru2 C34 122.01(19) . . ?
N2 Ru2 C34 160.1(2) . . ?
C39 Ru2 C34 67.6(2) . . ?
C30 Ru2 C34 80.2(2) . . ?
C31 Ru2 C34 68.2(2) . . ?
C33 Ru2 C34 37.0(2) . . ?
C35 Ru2 C34 38.3(2) . . ?
O4 Ru2 Cl2 85.65(12) . . ?
N2 Ru2 Cl2 83.47(14) . . ?
C39 Ru2 Cl2 121.59(17) . . ?
C30 Ru2 Cl2 159.85(16) . . ?
C31 Ru2 Cl2 154.58(17) . . ?
C33 Ru2 Cl2 117.26(17) . . ?
C35 Ru2 Cl2 94.02(17) . . ?
C34 Ru2 Cl2 93.29(17) . . ?
C13 C14 C15 121.9(6) . . ?
C13 C14 Ru1 71.7(3) . . ?
C15 C14 Ru1 71.7(3) . . ?
C33 C34 C35 120.4(6) . . ?
C33 C34 Ru2 70.4(4) . . ?
C35 C34 Ru2 70.2(4) . . ?
C8 C7 C6 123.4(6) . . ?
C8 C7 Cl3 118.6(5) . . ?
C6 C7 Cl3 117.9(5) . . ?
O3 C6 C7 124.8(6) . . ?
O3 C6 C5 118.7(5) . . ?
C7 C6 C5 116.4(5) . . ?
C27 C26 C25 124.3(5) . . ?
C27 C26 Cl4 118.6(4) . . ?
C25 C26 Cl4 117.1(4) . . ?
O6 C25 C26 125.9(6) . . ?
O6 C25 C24 117.2(5) . . ?
C26 C25 C24 116.8(5) . . ?
N2 C28 C23 122.0(5) . . ?
N2 C28 C27 115.0(5) . . ?
C23 C28 C27 123.0(5) . . ?
Cl6 C40 Cl5 112.2(5) . . ?
Cl6A C40A Cl5A 111.2(19) . . ?
Cl7 C41 Cl8 112.1(5) . . ?
Cl7A C41A Cl8A 115.6(17) . . ?

_refine_diff_density_max         1.347
_refine_diff_density_min         -1.656
_refine_diff_density_rms         0.127

