# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1009208'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H8 Cl2 N2 O2 Ru), (I2)'
_chemical_formula_sum            'C12 H8 Cl2 I N2 O2 Ru'
_chemical_formula_weight         511.07

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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.6617(2)
_cell_length_b                   9.4643(2)
_cell_length_c                   13.0807(4)
_cell_angle_alpha                70.4400(10)
_cell_angle_beta                 80.9530(10)
_cell_angle_gamma                83.3070(10)
_cell_volume                     765.64(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    101(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      37.72

_exptl_crystal_description       block
_exptl_crystal_colour            'reddish brown'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             482
_exptl_absorpt_coefficient_mu    3.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4430
_exptl_absorpt_correction_T_max  0.7828
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      101(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite crystal'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28379
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         37.97
_reflns_number_total             8276
_reflns_number_gt                7017
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2e (Brandenburg, 2010)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0187P)²+0.3362P] 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         8276
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0465
_refine_ls_wR_factor_gt          0.0440
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I3 I 0.989756(14) 1.347919(10) 0.544876(7) 0.01607(2) Uani 1 1 d . . .
Ru1 Ru 0.720309(16) 0.926394(11) 0.802921(9) 0.01128(2) Uani 1 1 d . . .
Cl1 Cl 0.93351(5) 1.01219(3) 0.63250(3) 0.01507(5) Uani 1 1 d . . .
Cl2 Cl 0.50920(5) 0.80721(4) 0.96940(3) 0.01581(6) Uani 1 1 d . . .
O1 O 0.95444(19) 1.10197(13) 0.89413(10) 0.0233(2) Uani 1 1 d . . .
O2 O 0.4226(2) 1.19900(14) 0.74710(12) 0.0285(3) Uani 1 1 d . . .
N1 N 0.59010(17) 0.79975(13) 0.72803(9) 0.01302(18) Uani 1 1 d . . .
N2 N 0.91280(17) 0.72625(12) 0.83508(9) 0.01214(18) Uani 1 1 d . . .
C1 C 0.8626(2) 1.03280(15) 0.86465(12) 0.0160(2) Uani 1 1 d . . .
C2 C 0.5336(2) 1.09644(17) 0.76847(13) 0.0183(2) Uani 1 1 d . . .
C10 C 0.4354(2) 0.84898(16) 0.66705(12) 0.0172(2) Uani 1 1 d . . .
H10 H 0.3750 0.9478 0.6578 0.021 Uiso 1 1 calc R . .
C11 C 0.3609(2) 0.76137(18) 0.61732(13) 0.0193(3) Uani 1 1 d . . .
H11 H 0.2550 0.8006 0.5725 0.023 Uiso 1 1 calc R . .
C12 C 0.4436(2) 0.61554(18) 0.63417(13) 0.0190(3) Uani 1 1 d . . .
H12 H 0.3925 0.5520 0.6028 0.023 Uiso 1 1 calc R . .
C13 C 0.6024(2) 0.56313(16) 0.69762(12) 0.0165(2) Uani 1 1 d . . .
H13 H 0.6600 0.4630 0.7108 0.020 Uiso 1 1 calc R . .
C14 C 0.6763(2) 0.65860(15) 0.74168(11) 0.0123(2) Uani 1 1 d . . .
C15 C 0.8569(2) 0.61794(14) 0.80097(11) 0.0123(2) Uani 1 1 d . . .
C16 C 0.9698(2) 0.48076(15) 0.81717(12) 0.0160(2) Uani 1 1 d . . .
H16 H 0.9282 0.4061 0.7928 0.019 Uiso 1 1 calc R . .
C17 C 1.1439(2) 0.45342(16) 0.86922(12) 0.0170(2) Uani 1 1 d . . .
H17 H 1.2218 0.3599 0.8815 0.020 Uiso 1 1 calc R . .
C18 C 1.2015(2) 0.56543(16) 0.90272(11) 0.0154(2) Uani 1 1 d . . .
H18 H 1.3206 0.5503 0.9376 0.019 Uiso 1 1 calc R . .
C19 C 1.0827(2) 0.70005(15) 0.88454(11) 0.0140(2) Uani 1 1 d . . .
H19 H 1.1226 0.7764 0.9078 0.017 Uiso 1 1 calc R . .


_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
I3 I3 2.73167(18) 2_786 yes
I3 Cl1 3.0421(3) . yes
Ru1 C2 1.8881(15) . yes
Ru1 C1 1.8901(14) . yes
Ru1 N1 2.1081(11) . yes
Ru1 N2 2.1165(11) . yes
Ru1 Cl1 2.3890(3) . yes
Ru1 Cl2 2.3988(4) . yes
O1 C1 1.1349(18) . ?
O2 C2 1.1328(18) . ?
N1 C10 1.3464(17) . ?
N1 C14 1.3564(17) . ?
N2 C19 1.3487(17) . ?
N2 C15 1.3550(17) . ?
C10 C11 1.384(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3899(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.4776(18) . ?
C15 C16 1.3908(18) . ?
C16 C17 1.392(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3881(19) . ?
C18 H18 0.9500 . ?
C19 H19 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
I3 I3 Cl1 174.566(8) 2_786 . yes
C2 Ru1 C1 87.31(6) . . yes
C2 Ru1 N1 97.09(5) . . ?
C1 Ru1 N1 174.30(5) . . ?
C2 Ru1 N2 174.70(5) . . ?
C1 Ru1 N2 97.99(5) . . ?
N1 Ru1 N2 77.63(4) . . yes
C2 Ru1 Cl1 93.75(5) . . ?
C1 Ru1 Cl1 90.81(5) . . ?
N1 Ru1 Cl1 85.31(3) . . ?
N2 Ru1 Cl1 86.31(3) . . ?
C2 Ru1 Cl2 91.65(5) . . ?
C1 Ru1 Cl2 95.38(5) . . ?
N1 Ru1 Cl2 88.13(3) . . ?
N2 Ru1 Cl2 87.77(3) . . ?
Cl1 Ru1 Cl2 171.973(12) . . yes
Ru1 Cl1 I3 115.760(12) . . ?
C10 N1 C14 118.84(12) . . ?
C10 N1 Ru1 125.50(9) . . ?
C14 N1 Ru1 115.63(8) . . ?
C19 N2 C15 118.89(11) . . ?
C19 N2 Ru1 125.72(9) . . ?
C15 N2 Ru1 115.39(8) . . ?
O1 C1 Ru1 174.95(14) . . ?
O2 C2 Ru1 179.46(17) . . ?
N1 C10 C11 122.61(13) . . ?
N1 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C12 C11 C10 118.71(13) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 119.15(13) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 119.42(13) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N1 C14 C13 121.17(12) . . ?
N1 C14 C15 115.54(11) . . ?
C13 C14 C15 123.22(12) . . ?
N2 C15 C16 121.29(12) . . ?
N2 C15 C14 115.61(11) . . ?
C16 C15 C14 123.04(12) . . ?
C15 C16 C17 119.71(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 118.66(12) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 119.11(12) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
N2 C19 C18 122.33(13) . . ?
N2 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        37.97
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.084
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.115
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1009209'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Br2 N2 O2 Ru, C H Cl3, I4'
_chemical_formula_sum            'C13 H9 Br2 Cl3 I4 N2 O2 Ru'
_chemical_formula_weight         846.26

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'
Br Br -0.2901 2.4595 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   6.65530(10)
_cell_length_b                   16.3426(4)
_cell_length_c                   10.2145(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.8650(10)
_cell_angle_gamma                90.00
_cell_volume                     1100.53(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6538
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      33.14

_exptl_crystal_description       plate
_exptl_crystal_colour            'brownish red'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    7.522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2120
_exptl_absorpt_correction_T_max  0.5445
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite crystal'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26564
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         31.49
_reflns_number_total             7286
_reflns_number_gt                6465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2g (Brandenburg, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0260P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.053(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         7286
_refine_ls_number_parameters     227
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0239
_refine_ls_wR_factor_ref         0.0558
_refine_ls_wR_factor_gt          0.0542
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I3 I 0.15139(3) 0.249773(15) -0.09244(2) 0.02405(5) Uani 1 1 d . . .
I4 I -0.22333(3) 0.249130(16) -0.23757(2) 0.02369(5) Uani 1 1 d . . .
Ru1 Ru 0.45978(3) 0.265067(12) 0.33083(3) 0.01333(5) Uani 1 1 d . . .
Br1 Br 0.57840(5) 0.27875(2) 0.10649(3) 0.01929(7) Uani 1 1 d . . .
Br2 Br 0.33800(4) 0.25586(2) 0.55569(3) 0.01806(6) Uani 1 1 d . . .
Cl1 Cl 0.5193(2) 0.46645(9) 0.74726(18) 0.0603(4) Uani 1 1 d . . .
Cl2 Cl 0.15105(18) 0.49520(9) 0.85870(13) 0.0478(3) Uani 1 1 d . . .
Cl3 Cl 0.53576(19) 0.54816(8) 0.99965(14) 0.0464(3) Uani 1 1 d . . .
O1 O 0.7618(4) 0.13127(18) 0.4123(3) 0.0348(7) Uani 1 1 d . . .
O2 O 0.1518(4) 0.13564(16) 0.2355(3) 0.0290(6) Uani 1 1 d . . .
N1 N 0.2703(4) 0.36713(17) 0.2801(3) 0.0150(5) Uani 1 1 d . . .
N2 N 0.6471(4) 0.36456(17) 0.4021(3) 0.0169(6) Uani 1 1 d . . .
C1 C 0.6483(6) 0.1814(2) 0.3802(4) 0.0220(7) Uani 1 1 d . . .
C2 C 0.2690(5) 0.1840(2) 0.2693(4) 0.0188(7) Uani 1 1 d . . .
C10 C 0.0831(5) 0.3641(2) 0.2120(4) 0.0158(6) Uani 1 1 d . . .
H10 H 0.0242 0.3121 0.1901 0.019 Uiso 1 1 calc R . .
C11 C -0.0282(6) 0.4338(2) 0.1721(4) 0.0249(7) Uani 1 1 d . . .
H11 H -0.1611 0.4297 0.1250 0.030 Uiso 1 1 calc R . .
C12 C 0.0590(6) 0.5093(2) 0.2027(4) 0.0282(8) Uani 1 1 d . . .
H12 H -0.0116 0.5581 0.1743 0.034 Uiso 1 1 calc R . .
C13 C 0.2498(6) 0.5133(2) 0.2747(4) 0.0264(8) Uani 1 1 d . . .
H13 H 0.3099 0.5647 0.2991 0.032 Uiso 1 1 calc R . .
C14 C 0.3529(5) 0.44135(19) 0.3112(4) 0.0182(6) Uani 1 1 d . . .
C15 C 0.5607(5) 0.4400(2) 0.3842(4) 0.0189(6) Uani 1 1 d . . .
C16 C 0.6647(6) 0.5092(2) 0.4335(4) 0.0282(9) Uani 1 1 d . . .
H16 H 0.6032 0.5616 0.4207 0.034 Uiso 1 1 calc R . .
C17 C 0.8581(6) 0.5018(3) 0.5015(4) 0.0322(10) Uani 1 1 d . . .
H17 H 0.9302 0.5488 0.5367 0.039 Uiso 1 1 calc R . .
C18 C 0.9434(5) 0.4265(3) 0.5172(4) 0.0264(8) Uani 1 1 d . . .
H18 H 1.0767 0.4205 0.5631 0.032 Uiso 1 1 calc R . .
C19 C 0.8365(5) 0.3586(2) 0.4666(4) 0.0208(7) Uani 1 1 d . . .
H19 H 0.8985 0.3062 0.4776 0.025 Uiso 1 1 calc R . .
C20 C 0.4087(6) 0.4725(3) 0.8968(5) 0.0376(11) Uani 1 1 d . . .
H20 H 0.4242 0.4185 0.9431 0.045 Uiso 1 1 calc R . .


_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
I3 I4 2.7212(3) . yes
I3 Br1 3.2938(4) . yes
Ru1 C1 1.878(4) . yes
Ru1 C2 1.883(4) . yes
Ru1 N1 2.112(3) . yes
Ru1 N2 2.117(3) . yes
Ru1 Br1 2.5337(4) . yes
Ru1 Br2 2.5424(4) . yes
Cl1 C20 1.787(6) . ?
Cl2 C20 1.745(4) . ?
Cl3 C20 1.762(5) . ?
O1 C1 1.132(4) . ?
O2 C2 1.131(4) . ?
N1 C10 1.342(4) . ?
N1 C14 1.352(4) . ?
N2 C19 1.343(4) . ?
N2 C15 1.362(4) . ?
C10 C11 1.389(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.386(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.478(5) . ?
C15 C16 1.384(5) . ?
C16 C17 1.382(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.355(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(5) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20 1.0000 . ?

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
I4 I3 Br1 170.280(12) . . yes
C1 Ru1 C2 88.41(16) . . yes
C1 Ru1 N1 174.60(14) . . ?
C2 Ru1 N1 96.95(12) . . ?
C1 Ru1 N2 97.28(13) . . ?
C2 Ru1 N2 173.78(13) . . ?
N1 Ru1 N2 77.39(11) . . yes
C1 Ru1 Br1 91.59(12) . . ?
C2 Ru1 Br1 92.28(11) . . ?
N1 Ru1 Br1 87.59(8) . . ?
N2 Ru1 Br1 90.08(8) . . ?
C1 Ru1 Br2 89.89(12) . . ?
C2 Ru1 Br2 88.62(11) . . ?
N1 Ru1 Br2 90.85(8) . . ?
N2 Ru1 Br2 88.88(8) . . ?
Br1 Ru1 Br2 178.284(15) . . yes
Ru1 Br1 I3 101.300(12) . . yes
C10 N1 C14 118.3(3) . . ?
C10 N1 Ru1 125.4(2) . . ?
C14 N1 Ru1 116.1(2) . . ?
C19 N2 C15 118.8(3) . . ?
C19 N2 Ru1 125.6(2) . . ?
C15 N2 Ru1 115.5(2) . . ?
O1 C1 Ru1 178.7(4) . . ?
O2 C2 Ru1 178.1(3) . . ?
N1 C10 C11 122.8(3) . . ?
N1 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C12 C11 C10 118.4(4) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C13 C12 C11 119.3(3) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
N1 C14 C13 121.8(3) . . ?
N1 C14 C15 115.3(3) . . ?
C13 C14 C15 122.9(3) . . ?
N2 C15 C16 120.6(3) . . ?
N2 C15 C14 115.4(3) . . ?
C16 C15 C14 123.9(3) . . ?
C17 C16 C15 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 120.0(4) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
N2 C19 C18 121.7(3) . . ?
N2 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
Cl2 C20 Cl3 111.1(3) . . ?
Cl2 C20 Cl1 109.2(3) . . ?
Cl3 C20 Cl1 109.2(2) . . ?
Cl2 C20 H20 109.1 . . ?
Cl3 C20 H20 109.1 . . ?
Cl1 C20 H20 109.1 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20 I3 1.00 3.29 4.031(4) 131.9 1_556 yes
C20 H20 Br1 1.00 2.93 3.903(4) 164.3 1_556 yes

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        31.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.301
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.126
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1009210'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 I4 N2 O2 Ru, 2(I4)'
_chemical_formula_sum            'C12 H8 I6 N2 O2 Ru'
_chemical_formula_weight         1074.67

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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'

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

_cell_length_a                   15.6811(6)
_cell_length_b                   7.3656(3)
_cell_length_c                   9.4737(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1094.22(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      40.17

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    3.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    9.188
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0819
_exptl_absorpt_correction_T_max  0.3357
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'flat graphite crystal'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_device       
'62mm x 62mm CCD camera on three-circle goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22615
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         37.78
_reflns_number_total             5875
_reflns_number_gt                5640
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Brandenburg, 2010)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0084P)²+0.4463P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_chemical_absolute_configuration unk
_refine_ls_abs_structure_Flack   0.014(16)
_refine_ls_number_reflns         5875
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0208
_refine_ls_R_factor_gt           0.0193
_refine_ls_wR_factor_ref         0.0404
_refine_ls_wR_factor_gt          0.0400
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I3 I 0.309615(9) 0.33667(2) 0.536555(15) 0.01531(3) Uani 1 1 d . . .
I4 I 0.278422(9) 0.35766(2) 0.250795(16) 0.01683(3) Uani 1 1 d . . .
I1 I 0.348650(9) 0.32670(2) 0.867829(15) 0.01641(3) Uani 1 1 d . . .
Ru1 Ru 0.5000 0.5000 0.86204(3) 0.01095(4) Uani 1 2 d S . .
O2 O 0.44529(13) 0.7646(3) 0.6348(2) 0.0246(4) Uani 1 1 d . . .
N1 N 0.46031(11) 0.6574(3) 1.03583(19) 0.0121(3) Uani 1 1 d . . .
C2 C 0.46433(14) 0.6633(4) 0.7204(2) 0.0165(4) Uani 1 1 d . . .
C10 C 0.41843(15) 0.8164(3) 1.0283(3) 0.0174(4) Uani 1 1 d . . .
H10 H 0.4048 0.8637 0.9378 0.021 Uiso 1 1 calc R . .
C11 C 0.39439(16) 0.9137(4) 1.1461(3) 0.0208(5) Uani 1 1 d . . .
H11 H 0.3636 1.0242 1.1367 0.025 Uiso 1 1 calc R . .
C12 C 0.41582(15) 0.8479(4) 1.2783(3) 0.0207(5) Uani 1 1 d . . .
H12 H 0.4017 0.9141 1.3611 0.025 Uiso 1 1 calc R . .
C13 C 0.45824(16) 0.6837(4) 1.2874(2) 0.0177(4) Uani 1 1 d . . .
H13 H 0.4732 0.6355 1.3771 0.021 Uiso 1 1 calc R . .
C14 C 0.47889(14) 0.5892(3) 1.1650(2) 0.0132(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I3 I4 2.7554(2) . yes
I3 I1 3.1984(2) . yes
I4 I1 3.7984(3) 1_554 yes
I1 Ru1 2.69540(16) . yes
Ru1 C2 1.887(3) . yes
Ru1 C2 1.887(3) 2_665 ?
Ru1 N1 2.1077(19) . yes
Ru1 N1 2.1078(19) 2_665 ?
Ru1 I1 2.69536(16) 2_665 ?
O2 C2 1.142(3) . ?
N1 C10 1.344(3) . ?
N1 C14 1.355(3) . ?
C10 C11 1.379(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(3) . ?
C13 H13 0.9500 . ?
C14 C14 1.471(5) 2_665 ?

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
I4 I3 I1 177.941(7) . . yes
I3 I4 I1 152.083(6) . 1_554 yes
Ru1 I1 I3 97.914(7) . . yes
C2 Ru1 C2 89.33(15) . 2_665 ?
C2 Ru1 N1 96.74(9) . . yes
C2 Ru1 N1 173.59(10) 2_665 . ?
C2 Ru1 N1 173.59(10) . 2_665 ?
C2 Ru1 N1 96.74(9) 2_665 2_665 ?
N1 Ru1 N1 77.27(11) . 2_665 yes
C2 Ru1 I1 88.49(7) . 2_665 ?
C2 Ru1 I1 93.17(7) 2_665 2_665 ?
N1 Ru1 I1 89.06(5) . 2_665 ?
N1 Ru1 I1 89.12(5) 2_665 2_665 ?
C2 Ru1 I1 93.17(7) . . ?
C2 Ru1 I1 88.49(7) 2_665 . ?
N1 Ru1 I1 89.12(5) . . ?
N1 Ru1 I1 89.06(5) 2_665 . ?
I1 Ru1 I1 177.668(12) 2_665 . ?
C10 N1 C14 118.4(2) . . ?
C10 N1 Ru1 125.58(16) . . ?
C14 N1 Ru1 115.97(15) . . ?
O2 C2 Ru1 177.8(2) . . ?
N1 C10 C11 122.9(2) . . ?
N1 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C10 C11 C12 118.9(2) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
C13 C12 C11 118.7(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 119.8(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
N1 C14 C13 121.2(2) . . ?
N1 C14 C14 115.35(13) . 2_665 ?
C13 C14 C14 123.48(15) . 2_665 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        37.78
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.814
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.140
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1009211'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 I2 N2 O2 Ru, I2'
_chemical_formula_sum            'C12 H8 I4 N2 O2 Ru'
_chemical_formula_weight         820.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.0961(16)
_cell_length_b                   10.371(3)
_cell_length_c                   10.572(3)
_cell_angle_alpha                112.39(3)
_cell_angle_beta                 93.49(3)
_cell_angle_gamma                90.70(2)
_cell_volume                     919.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6397
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      31.71

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.964
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    7.568
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3736
_exptl_absorpt_correction_T_max  0.5556
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'flat graphite crystal'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_device       
'62mm x 62mm CCD camera on three-circle goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8005
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0336
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4225
_reflns_number_gt                3399
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2g (Brandenburg, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0411P)²+9.4494P] 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         4225
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0879
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.71384(6) 0.03380(5) 0.64462(6) 0.02812(13) Uani 1 1 d . . .
I2 I 0.94515(6) 0.52562(5) 0.69581(5) 0.02743(13) Uani 1 1 d . . .
I3 I 0.47762(5) 0.14184(5) 0.87882(5) 0.02259(12) Uani 1 1 d . . .
I4 I 0.26891(6) 0.25858(5) 1.06388(5) 0.02591(13) Uani 1 1 d . . .
Ru1 Ru 0.83161(6) 0.28387(6) 0.67779(6) 0.01569(13) Uani 1 1 d . . .
O1 O 1.1373(6) 0.1834(6) 0.7037(6) 0.0303(13) Uani 1 1 d . . .
O2 O 0.8220(7) 0.3910(7) 0.9859(6) 0.0342(14) Uani 1 1 d . . .
N1 N 0.6173(6) 0.3433(6) 0.6352(6) 0.0164(11) Uani 1 1 d . . .
N2 N 0.8194(6) 0.2202(6) 0.4620(6) 0.0171(12) Uani 1 1 d . . .
C1 C 1.0248(9) 0.2222(8) 0.6963(7) 0.0223(15) Uani 1 1 d . . .
C2 C 0.8258(8) 0.3505(8) 0.8716(9) 0.0264(17) Uani 1 1 d . . .
C10 C 0.5208(8) 0.4036(7) 0.7276(8) 0.0190(14) Uani 1 1 d . . .
H10 H 0.5509 0.4298 0.8220 0.023 Uiso 1 1 calc R . .
C11 C 0.3785(8) 0.4298(8) 0.6925(8) 0.0219(15) Uani 1 1 d . . .
H11 H 0.3126 0.4735 0.7613 0.026 Uiso 1 1 calc R . .
C12 C 0.3347(8) 0.3916(8) 0.5566(8) 0.0230(15) Uani 1 1 d . . .
H12 H 0.2369 0.4061 0.5296 0.028 Uiso 1 1 calc R . .
C13 C 0.4349(8) 0.3313(8) 0.4586(8) 0.0215(15) Uani 1 1 d . . .
H13 H 0.4070 0.3064 0.3640 0.026 Uiso 1 1 calc R . .
C14 C 0.5767(8) 0.3076(7) 0.5006(7) 0.0187(14) Uani 1 1 d . . .
C15 C 0.6907(7) 0.2465(7) 0.4048(7) 0.0153(13) Uani 1 1 d . . .
C16 C 0.6743(8) 0.2164(8) 0.2642(8) 0.0223(15) Uani 1 1 d . . .
H16 H 0.5848 0.2356 0.2247 0.027 Uiso 1 1 calc R . .
C17 C 0.7879(9) 0.1586(8) 0.1826(8) 0.0261(16) Uani 1 1 d . . .
H17 H 0.7771 0.1376 0.0868 0.031 Uiso 1 1 calc R . .
C18 C 0.9163(9) 0.1319(8) 0.2408(8) 0.0232(15) Uani 1 1 d . . .
H18 H 0.9957 0.0917 0.1862 0.028 Uiso 1 1 calc R . .
C19 C 0.9284(8) 0.1650(8) 0.3817(8) 0.0222(15) Uani 1 1 d . . .
H19 H 1.0180 0.1475 0.4223 0.027 Uiso 1 1 calc R . .


_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
I1 Ru1 2.6816(12) . yes
I1 I3 3.2553(13) . yes
I2 Ru1 2.6340(11) . yes
I3 I4 2.7572(12) . yes
I4 I2 3.4108(15) 2_667 yes
Ru1 C1 1.901(8) . yes
Ru1 C2 1.902(8) . yes
Ru1 N2 2.115(6) . yes
Ru1 N1 2.125(6) . yes
O1 C1 1.113(9) . ?
O2 C2 1.121(10) . ?
N1 C10 1.330(9) . ?
N1 C14 1.353(9) . ?
N2 C19 1.333(9) . ?
N2 C15 1.362(9) . ?
C10 C11 1.383(10) . ?
C10 H10 0.9500 . ?
C11 C12 1.368(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.469(10) . ?
C15 C16 1.396(10) . ?
C16 C17 1.379(11) . ?
C16 H16 0.9500 . ?
C17 C18 1.367(11) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(10) . ?
C18 H18 0.9500 . ?
C19 H19 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
Ru1 I1 I3 97.80(4) . . yes
I4 I3 I1 172.75(2) . . yes
I3 I4 I2 166.50(2) . 2_667 yes
C1 Ru1 C2 88.7(3) . . yes
C1 Ru1 N2 96.7(3) . . ?
C2 Ru1 N2 174.5(3) . . ?
C1 Ru1 N1 174.2(3) . . ?
C2 Ru1 N1 97.1(3) . . ?
N2 Ru1 N1 77.5(2) . . yes
C1 Ru1 I2 89.7(2) . . ?
C2 Ru1 I2 90.8(2) . . ?
N2 Ru1 I2 88.18(16) . . ?
N1 Ru1 I2 90.68(15) . . ?
C1 Ru1 I1 91.0(2) . . ?
C2 Ru1 I1 92.2(2) . . ?
N2 Ru1 I1 88.72(16) . . ?
N1 Ru1 I1 88.38(15) . . ?
I2 Ru1 I1 176.88(3) . . yes
C10 N1 C14 119.1(6) . . ?
C10 N1 Ru1 125.7(5) . . ?
C14 N1 Ru1 115.1(5) . . ?
C19 N2 C15 119.1(6) . . ?
C19 N2 Ru1 125.4(5) . . ?
C15 N2 Ru1 115.4(5) . . ?
O1 C1 Ru1 178.1(7) . . ?
O2 C2 Ru1 179.3(8) . . ?
N1 C10 C11 122.9(7) . . ?
N1 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C12 C11 C10 118.6(7) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C13 119.4(7) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 119.3(7) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 120.7(7) . . ?
N1 C14 C15 116.1(6) . . ?
C13 C14 C15 123.2(7) . . ?
N2 C15 C16 120.1(6) . . ?
N2 C15 C14 115.5(6) . . ?
C16 C15 C14 124.3(6) . . ?
C17 C16 C15 120.0(7) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.4(7) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 118.6(7) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
N2 C19 C18 122.8(7) . . ?
N2 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.624
_refine_diff_density_min         -2.493
_refine_diff_density_rms         0.230
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1009212'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Br1 N2 O2 Ru, C H Cl3, I3'
_chemical_formula_sum            'C13 H9 Br1 Cl3 I3 N2 O2 Ru'
_chemical_formula_weight         846.26

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'
Br Br -0.2901 2.4595 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   11.6841(6)
_cell_length_b                   11.4179(6)
_cell_length_c                   17.2077(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.9460(10)
_cell_angle_gamma                90.00
_cell_volume                     2207.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      34.32

_exptl_crystal_description       block
_exptl_crystal_colour            'reddish brown'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    7.501
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2017
_exptl_absorpt_correction_T_max  0.4664
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'curved graphite crystal'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            66442
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         30.50
_reflns_number_total             6749
_reflns_number_gt                5724
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2g (Brandenburg, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0210P)²+3.9430P] 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         6749
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0494
_refine_ls_wR_factor_gt          0.0454
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I4 I 0.896400(16) -0.005360(15) 0.604220(11) 0.02190(4) Uani 1 1 d . . .
I3 I 0.837680(16) -0.219269(15) 0.651552(10) 0.02005(4) Uani 1 1 d . . .
Ru1 Ru 0.848072(17) 0.391460(17) 0.617383(11) 0.01286(4) Uani 1 1 d . . .
Br2 Br 0.93978(2) 0.25536(2) 0.534530(16) 0.01753(5) Uani 1 1 d . . .
Br1 Br 0.74928(2) 0.52658(2) 0.695398(15) 0.01772(5) Uani 1 1 d . . .
Cl1 Cl 0.27883(9) 0.31263(8) 0.80641(5) 0.0412(2) Uani 1 1 d . . .
Cl2 Cl 0.14600(7) 0.40860(7) 0.91006(5) 0.03108(15) Uani 1 1 d . . .
Cl3 Cl 0.26459(9) 0.56444(8) 0.82433(6) 0.0485(2) Uani 1 1 d . . .
O1 O 1.06727(18) 0.54436(19) 0.65260(13) 0.0272(4) Uani 1 1 d . . .
O2 O 0.95564(19) 0.24926(19) 0.76761(13) 0.0288(5) Uani 1 1 d . . .
N1 N 0.68570(18) 0.29876(18) 0.58161(12) 0.0145(4) Uani 1 1 d . . .
N2 N 0.75605(19) 0.47709(18) 0.50916(12) 0.0147(4) Uani 1 1 d . . .
C1 C 0.9866(2) 0.4867(2) 0.64049(15) 0.0179(5) Uani 1 1 d . . .
C2 C 0.9172(2) 0.3030(2) 0.71216(16) 0.0191(5) Uani 1 1 d . . .
C10 C 0.6552(2) 0.2100(2) 0.62317(16) 0.0184(5) Uani 1 1 d . . .
H10 H 0.7115 0.1835 0.6709 0.022 Uiso 1 1 calc R . .
C11 C 0.5452(3) 0.1557(3) 0.59935(17) 0.0231(5) Uani 1 1 d . . .
H11 H 0.5263 0.0932 0.6301 0.028 Uiso 1 1 calc R . .
C12 C 0.4629(2) 0.1945(2) 0.52928(18) 0.0235(6) Uani 1 1 d . . .
H12 H 0.3868 0.1588 0.5114 0.028 Uiso 1 1 calc R . .
C13 C 0.4935(2) 0.2859(2) 0.48607(16) 0.0208(5) Uani 1 1 d . . .
H13 H 0.4382 0.3140 0.4384 0.025 Uiso 1 1 calc R . .
C14 C 0.6060(2) 0.3365(2) 0.51306(15) 0.0150(4) Uani 1 1 d . . .
C15 C 0.6471(2) 0.4331(2) 0.47102(15) 0.0147(4) Uani 1 1 d . . .
C16 C 0.5807(2) 0.4781(2) 0.39705(16) 0.0201(5) Uani 1 1 d . . .
H16 H 0.5052 0.4457 0.3706 0.024 Uiso 1 1 calc R . .
C17 C 0.6259(3) 0.5706(3) 0.36253(16) 0.0231(6) Uani 1 1 d . . .
H17 H 0.5818 0.6023 0.3122 0.028 Uiso 1 1 calc R . .
C18 C 0.7363(3) 0.6163(3) 0.40251(17) 0.0228(5) Uani 1 1 d . . .
H18 H 0.7687 0.6803 0.3803 0.027 Uiso 1 1 calc R . .
C19 C 0.7984(2) 0.5672(2) 0.47516(16) 0.0179(5) Uani 1 1 d . . .
H19 H 0.8743 0.5984 0.5022 0.021 Uiso 1 1 calc R . .
C20 C 0.2704(3) 0.4280(2) 0.87256(17) 0.0237(6) Uani 1 1 d . . .
H20 H 0.3437 0.4259 0.9192 0.028 Uiso 1 1 calc R . .


_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
I4 I3 2.7215(3) . yes
I4 Br2 3.3001(3) . yes
I3 Br1 3.2381(3) 1_545 yes
Ru1 C2 1.900(3) . yes
Ru1 C1 1.900(3) . yes
Ru1 N1 2.111(2) . yes
Ru1 N2 2.117(2) . yes
Ru1 Br1 2.5231(3) . yes
Ru1 Br2 2.5367(3) . yes
Cl1 C20 1.761(3) . ?
Cl2 C20 1.759(3) . ?
Cl3 C20 1.757(3) . ?
O1 C1 1.121(3) . ?
O2 C2 1.119(3) . ?
N1 C10 1.344(3) . ?
N1 C14 1.357(3) . ?
N2 C19 1.344(3) . ?
N2 C15 1.358(3) . ?
C10 C11 1.384(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.392(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.470(3) . ?
C15 C16 1.394(3) . ?
C16 C17 1.386(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20 1.0000 . ?

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
I3 I4 Br2 174.164(9) . . yes
I4 I3 Br1 175.405(9) . 1_545 yes
C2 Ru1 C1 89.32(11) . . yes
C2 Ru1 N1 96.87(10) . . ?
C1 Ru1 N1 173.75(10) . . ?
C2 Ru1 N2 173.92(9) . . ?
C1 Ru1 N2 96.74(9) . . ?
N1 Ru1 N2 77.08(8) . . yes
C2 Ru1 Br1 90.97(8) . . ?
C1 Ru1 Br1 91.52(8) . . ?
N1 Ru1 Br1 87.47(6) . . ?
N2 Ru1 Br1 89.41(6) . . ?
C2 Ru1 Br2 90.65(8) . . ?
C1 Ru1 Br2 90.07(8) . . ?
N1 Ru1 Br2 90.77(6) . . ?
N2 Ru1 Br2 88.82(6) . . ?
Br1 Ru1 Br2 177.743(12) . . yes
Ru1 Br2 I4 102.569(10) . . yes
C10 N1 C14 118.9(2) . . ?
C10 N1 Ru1 124.85(17) . . ?
C14 N1 Ru1 116.20(16) . . ?
C19 N2 C15 118.8(2) . . ?
C19 N2 Ru1 125.30(17) . . ?
C15 N2 Ru1 115.88(16) . . ?
O1 C1 Ru1 178.4(2) . . ?
O2 C2 Ru1 178.4(2) . . ?
N1 C10 C11 122.8(2) . . ?
N1 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C12 118.6(3) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C13 C12 C11 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
N1 C14 C13 121.2(2) . . ?
N1 C14 C15 115.3(2) . . ?
C13 C14 C15 123.5(2) . . ?
N2 C15 C16 121.2(2) . . ?
N2 C15 C14 115.4(2) . . ?
C16 C15 C14 123.4(2) . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 119.1(2) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
N2 C19 C18 122.7(2) . . ?
N2 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
Cl3 C20 Cl2 110.87(16) . . ?
Cl3 C20 Cl1 111.07(16) . . ?
Cl2 C20 Cl1 109.95(16) . . ?
Cl3 C20 H20 108.3 . . ?
Cl2 C20 H20 108.3 . . ?
Cl1 C20 H20 108.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C20 H20 I4 1.00 3.20 3.951(3) 132.8 4_566 yes
C20 H20 Br2 1.00 2.87 3.611(3) 131.1 4_566 yes

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.290
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.122
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1009213'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Cl2 N2 O2 Ru, C H2 Cl2'
_chemical_formula_sum            'C13 H10 Cl4 N2 O2 Ru'
_chemical_formula_weight         469.10

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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   6.4683(3)
_cell_length_b                   12.3842(5)
_cell_length_c                   21.1414(9)
_cell_angle_alpha                89.106(2)
_cell_angle_beta                 83.451(2)
_cell_angle_gamma                87.535(2)
_cell_volume                     1680.82(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      33.19

_exptl_crystal_description       Needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    1.574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5109
_exptl_absorpt_correction_T_max  0.7274
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'flat graphite crystal'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_device       
'62mm x 62mm CCD camera on three-circle goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_reflns_number            42866
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.65
_diffrn_reflns_theta_max         33.20
_reflns_number_total             12621
_reflns_number_gt                10368
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2g (Brandenburg, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0348P)²+1.6211P] 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         12621
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0703
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.89792(2) 0.240599(11) 0.433426(6) 0.01273(3) Uani 1 1 d . . .
Cl1 Cl 0.77170(7) 0.14383(3) 0.34927(2) 0.01744(8) Uani 1 1 d . . .
Cl2 Cl 1.03711(7) 0.34471(3) 0.51175(2) 0.01653(8) Uani 1 1 d . . .
Cl5 Cl 1.14064(12) -0.16670(8) 0.33928(5) 0.0648(3) Uani 1 1 d . . .
Cl6 Cl 0.70814(11) -0.16544(5) 0.31312(3) 0.03529(13) Uani 1 1 d . . .
Cl7 Cl 0.91484(9) 0.67484(4) 0.17169(3) 0.02876(11) Uani 1 1 d . . .
Cl8 Cl 0.46096(10) 0.70155(5) 0.19733(3) 0.03418(12) Uani 1 1 d . . .
O1 O 1.1878(3) 0.05264(12) 0.46095(8) 0.0296(3) Uani 1 1 d . . .
O2 O 0.5566(3) 0.15732(13) 0.52883(8) 0.0285(3) Uani 1 1 d . . .
N1 N 0.7212(2) 0.38024(12) 0.40972(7) 0.0140(3) Uani 1 1 d . . .
N2 N 1.1018(2) 0.31628(12) 0.36272(7) 0.0133(3) Uani 1 1 d . . .
C1 C 1.0773(3) 0.12269(15) 0.45051(9) 0.0183(3) Uani 1 1 d . . .
C2 C 0.6890(3) 0.18639(15) 0.49394(9) 0.0186(3) Uani 1 1 d . . .
C10 C 0.5284(3) 0.40884(15) 0.43655(8) 0.0156(3) Uani 1 1 d . . .
H10 H 0.4602 0.3615 0.4671 0.019 Uiso 1 1 calc R . .
C11 C 0.4251(3) 0.50470(15) 0.42137(9) 0.0184(3) Uani 1 1 d . . .
H11 H 0.2886 0.5223 0.4410 0.022 Uiso 1 1 calc R . .
C12 C 0.5241(3) 0.57385(15) 0.37724(10) 0.0202(4) Uani 1 1 d . . .
H12 H 0.4578 0.6406 0.3666 0.024 Uiso 1 1 calc R . .
C13 C 0.7227(3) 0.54452(15) 0.34845(10) 0.0193(3) Uani 1 1 d . . .
H13 H 0.7927 0.5907 0.3175 0.023 Uiso 1 1 calc R . .
C14 C 0.8175(3) 0.44711(14) 0.36543(8) 0.0146(3) Uani 1 1 d . . .
C15 C 1.0260(3) 0.40911(14) 0.33745(8) 0.0142(3) Uani 1 1 d . . .
C16 C 1.1404(3) 0.46317(15) 0.28819(9) 0.0190(3) Uani 1 1 d . . .
H16 H 1.0845 0.5276 0.2706 0.023 Uiso 1 1 calc R . .
C17 C 1.3367(3) 0.42256(16) 0.26489(9) 0.0192(3) Uani 1 1 d . . .
H17 H 1.4164 0.4584 0.2310 0.023 Uiso 1 1 calc R . .
C18 C 1.4152(3) 0.32879(15) 0.29181(8) 0.0168(3) Uani 1 1 d . . .
H18 H 1.5506 0.3002 0.2772 0.020 Uiso 1 1 calc R . .
C19 C 1.2931(3) 0.27774(14) 0.34025(8) 0.0149(3) Uani 1 1 d . . .
H19 H 1.3463 0.2131 0.3583 0.018 Uiso 1 1 calc R . .
C20 C 0.8792(4) -0.14140(18) 0.36978(11) 0.0267(4) Uani 1 1 d . . .
H20A H 0.8597 -0.0653 0.3836 0.032 Uiso 1 1 calc R . .
H20B H 0.8452 -0.1883 0.4076 0.032 Uiso 1 1 calc R . .
C21 C 0.6728(4) 0.64849(18) 0.14494(10) 0.0265(4) Uani 1 1 d . . .
H21A H 0.6607 0.5694 0.1414 0.032 Uiso 1 1 calc R . .
H21B H 0.6670 0.6810 0.1021 0.032 Uiso 1 1 calc R . .
Ru1B Ru 0.65186(2) 0.280816(11) 0.071387(6) 0.01254(3) Uani 1 1 d . . .
Cl1B Cl 0.51174(7) 0.19321(4) -0.01354(2) 0.01711(8) Uani 1 1 d . . .
Cl2B Cl 0.78880(7) 0.36055(3) 0.15948(2) 0.01675(8) Uani 1 1 d . . .
O1B O 0.3612(3) 0.47659(13) 0.06399(8) 0.0283(3) Uani 1 1 d . . .
O2B O 0.9898(3) 0.38314(12) -0.01716(7) 0.0253(3) Uani 1 1 d . . .
N1B N 0.8333(2) 0.13809(12) 0.08519(7) 0.0137(3) Uani 1 1 d . . .
N2B N 0.4534(2) 0.19239(12) 0.13746(7) 0.0136(3) Uani 1 1 d . . .
C1B C 0.4704(3) 0.40275(15) 0.06549(9) 0.0178(3) Uani 1 1 d . . .
C2B C 0.8573(3) 0.34710(15) 0.01487(9) 0.0175(3) Uani 1 1 d . . .
C10B C 1.0248(3) 0.11502(14) 0.05570(8) 0.0152(3) Uani 1 1 d . . .
H10B H 1.0880 0.1669 0.0270 0.018 Uiso 1 1 calc R . .
C11B C 1.1342(3) 0.01848(15) 0.06546(9) 0.0177(3) Uani 1 1 d . . .
H11B H 1.2701 0.0050 0.0442 0.021 Uiso 1 1 calc R . .
C12B C 1.0420(3) -0.05761(15) 0.10665(10) 0.0207(4) Uani 1 1 d . . .
H12B H 1.1122 -0.1250 0.1134 0.025 Uiso 1 1 calc R . .
C13B C 0.8451(3) -0.03398(15) 0.13797(10) 0.0204(4) Uani 1 1 d . . .
H13B H 0.7798 -0.0849 0.1669 0.025 Uiso 1 1 calc R . .
C14B C 0.7441(3) 0.06463(14) 0.12673(8) 0.0151(3) Uani 1 1 d . . .
C15B C 0.5354(3) 0.09682(14) 0.15789(8) 0.0150(3) Uani 1 1 d . . .
C16B C 0.4266(3) 0.03550(16) 0.20503(10) 0.0208(4) Uani 1 1 d . . .
H16B H 0.4866 -0.0306 0.2193 0.025 Uiso 1 1 calc R . .
C17B C 0.2289(3) 0.07160(16) 0.23126(9) 0.0206(4) Uani 1 1 d . . .
H17B H 0.1534 0.0312 0.2641 0.025 Uiso 1 1 calc R . .
C18B C 0.1441(3) 0.16722(15) 0.20882(9) 0.0177(3) Uani 1 1 d . . .
H18B H 0.0080 0.1926 0.2251 0.021 Uiso 1 1 calc R . .
C19B C 0.2611(3) 0.22532(14) 0.16214(8) 0.0151(3) Uani 1 1 d . . .
H19B H 0.2029 0.2912 0.1470 0.018 Uiso 1 1 calc R . .


_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
Ru1 C1 1.8819(19) . yes
Ru1 C2 1.890(2) . yes
Ru1 N2 2.1129(15) . yes
Ru1 N1 2.1169(15) . yes
Ru1 Cl2 2.3920(5) . yes
Ru1 Cl1 2.3979(5) . yes
Cl5 C20 1.756(3) . ?
Cl6 C20 1.758(2) . ?
Cl7 C21 1.769(2) . ?
Cl8 C21 1.771(2) . ?
O1 C1 1.135(2) . ?
O2 C2 1.132(2) . ?
N1 C10 1.345(2) . ?
N1 C14 1.356(2) . ?
N2 C19 1.344(2) . ?
N2 C15 1.356(2) . ?
C10 C11 1.389(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.470(3) . ?
C15 C16 1.388(3) . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
Ru1B C1B 1.8836(19) . yes
Ru1B C2B 1.8888(19) . yes
Ru1B N2B 2.1124(15) . yes
Ru1B N1B 2.1142(15) . yes
Ru1B Cl2B 2.3951(5) . yes
Ru1B Cl1B 2.3956(5) . yes
O1B C1B 1.134(2) . ?
O2B C2B 1.133(2) . ?
N1B C10B 1.343(2) . ?
N1B C14B 1.355(2) . ?
N2B C19B 1.342(2) . ?
N2B C15B 1.361(2) . ?
C10B C11B 1.388(2) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.381(3) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.389(3) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.390(3) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.474(3) . ?
C15B C16B 1.388(3) . ?
C16B C17B 1.393(3) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.384(3) . ?
C17B H17B 0.9500 . ?
C18B C19B 1.385(3) . ?
C18B H18B 0.9500 . ?
C19B H19B 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
C1 Ru1 C2 89.89(8) . . yes
C1 Ru1 N2 97.50(7) . . ?
C2 Ru1 N2 172.55(7) . . ?
C1 Ru1 N1 174.57(7) . . ?
C2 Ru1 N1 95.38(7) . . ?
N2 Ru1 N1 77.25(6) . . yes
C1 Ru1 Cl2 90.09(6) . . ?
C2 Ru1 Cl2 92.29(6) . . ?
N2 Ru1 Cl2 88.65(4) . . ?
N1 Ru1 Cl2 88.40(4) . . ?
C1 Ru1 Cl1 91.06(6) . . ?
C2 Ru1 Cl1 91.58(6) . . ?
N2 Ru1 Cl1 87.37(4) . . ?
N1 Ru1 Cl1 90.11(4) . . ?
Cl2 Ru1 Cl1 175.970(16) . . yes
C10 N1 C14 118.63(16) . . ?
C10 N1 Ru1 125.49(12) . . ?
C14 N1 Ru1 115.83(12) . . ?
C19 N2 C15 119.00(16) . . ?
C19 N2 Ru1 125.24(12) . . ?
C15 N2 Ru1 115.72(12) . . ?
O1 C1 Ru1 178.94(19) . . ?
O2 C2 Ru1 176.47(18) . . ?
N1 C10 C11 122.72(18) . . ?
N1 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C12 C11 C10 118.80(18) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 119.06(17) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 119.38(18) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N1 C14 C13 121.39(17) . . ?
N1 C14 C15 115.32(15) . . ?
C13 C14 C15 123.28(17) . . ?
N2 C15 C16 121.18(17) . . ?
N2 C15 C14 115.72(15) . . ?
C16 C15 C14 123.11(16) . . ?
C17 C16 C15 119.54(17) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 119.04(17) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 118.85(17) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
N2 C19 C18 122.38(17) . . ?
N2 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
Cl5 C20 Cl6 111.93(13) . . ?
Cl5 C20 H20A 109.2 . . ?
Cl6 C20 H20A 109.2 . . ?
Cl5 C20 H20B 109.2 . . ?
Cl6 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
Cl7 C21 Cl8 111.70(12) . . ?
Cl7 C21 H21A 109.3 . . ?
Cl8 C21 H21A 109.3 . . ?
Cl7 C21 H21B 109.3 . . ?
Cl8 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C1B Ru1B C2B 90.23(8) . . yes
C1B Ru1B N2B 96.97(7) . . ?
C2B Ru1B N2B 172.55(7) . . ?
C1B Ru1B N1B 174.27(7) . . ?
C2B Ru1B N1B 95.45(7) . . ?
N2B Ru1B N1B 77.32(6) . . yes
C1B Ru1B Cl2B 89.91(6) . . ?
C2B Ru1B Cl2B 89.79(6) . . ?
N2B Ru1B Cl2B 88.36(4) . . ?
N1B Ru1B Cl2B 89.42(4) . . ?
C1B Ru1B Cl1B 91.80(6) . . ?
C2B Ru1B Cl1B 92.47(6) . . ?
N2B Ru1B Cl1B 89.19(4) . . ?
N1B Ru1B Cl1B 88.66(4) . . ?
Cl2B Ru1B Cl1B 177.163(16) . . yes
C10B N1B C14B 118.69(15) . . ?
C10B N1B Ru1B 125.32(12) . . ?
C14B N1B Ru1B 115.98(12) . . ?
C19B N2B C15B 118.84(16) . . ?
C19B N2B Ru1B 125.36(12) . . ?
C15B N2B Ru1B 115.72(12) . . ?
O1B C1B Ru1B 177.80(18) . . ?
O2B C2B Ru1B 175.60(18) . . ?
N1B C10B C11B 122.68(17) . . ?
N1B C10B H10B 118.7 . . ?
C11B C10B H10B 118.7 . . ?
C12B C11B C10B 118.82(18) . . ?
C12B C11B H11B 120.6 . . ?
C10B C11B H11B 120.6 . . ?
C11B C12B C13B 118.93(18) . . ?
C11B C12B H12B 120.5 . . ?
C13B C12B H12B 120.5 . . ?
C12B C13B C14B 119.61(18) . . ?
C12B C13B H13B 120.2 . . ?
C14B C13B H13B 120.2 . . ?
N1B C14B C13B 121.24(17) . . ?
N1B C14B C15B 115.35(15) . . ?
C13B C14B C15B 123.41(17) . . ?
N2B C15B C16B 121.15(17) . . ?
N2B C15B C14B 115.43(15) . . ?
C16B C15B C14B 123.43(16) . . ?
C15B C16B C17B 119.49(18) . . ?
C15B C16B H16B 120.3 . . ?
C17B C16B H16B 120.3 . . ?
C18B C17B C16B 118.98(18) . . ?
C18B C17B H17B 120.5 . . ?
C16B C17B H17B 120.5 . . ?
C17B C18B C19B 118.80(18) . . ?
C17B C18B H18B 120.6 . . ?
C19B C18B H18B 120.6 . . ?
N2B C19B C18B 122.69(17) . . ?
N2B C19B H19B 118.7 . . ?
C18B C19B H19B 118.7 . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        33.20
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         1.215
_refine_diff_density_min         -1.394
_refine_diff_density_rms         0.112
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1009214'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 Br2 N2 O2 Ru'
_chemical_formula_sum            'C12 H8 Br2 N2 O2 Ru'
_chemical_formula_weight         473.09

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_Hall  'P -2yac'

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

_cell_length_a                   8.3627(6)
_cell_length_b                   6.9269(5)
_cell_length_c                   12.7050(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.490(2)
_cell_angle_gamma                90.00
_cell_volume                     715.66(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3943
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      32.97

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    6.676
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3913
_exptl_absorpt_correction_T_max  0.7761
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II CCD'
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_detector_area_resol_mean 16
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6862
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         30.75
_reflns_number_total             3189
_reflns_number_gt                2979
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2g (Brandenburg, 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0206P)²+0.0000P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.093(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3189
_refine_ls_number_parameters     173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0564
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.07912(4) 0.22165(4) 0.09284(3) 0.01417(7) Uani 1 1 d . . .
Br1 Br -0.07412(4) 0.03379(5) -0.07218(3) 0.01694(9) Uani 1 1 d . . .
Br2 Br 0.24251(4) 0.42050(6) 0.25126(3) 0.01734(9) Uani 1 1 d . . .
O1 O -0.0439(4) -0.0496(5) 0.2400(3) 0.0290(7) Uani 1 1 d . . .
O2 O -0.2188(4) 0.4679(5) 0.0816(3) 0.0289(7) Uani 1 1 d . . .
N1 N 0.1879(4) 0.3905(5) -0.0106(3) 0.0166(7) Uani 1 1 d . . .
N2 N 0.2941(4) 0.0626(5) 0.0900(3) 0.0162(7) Uani 1 1 d . . .
C1 C 0.0015(5) 0.0515(7) 0.1866(4) 0.0196(9) Uani 1 1 d . . .
C2 C -0.1089(6) 0.3798(7) 0.0853(3) 0.0210(9) Uani 1 1 d . . .
C10 C 0.1277(5) 0.5572(6) -0.0582(4) 0.0204(8) Uani 1 1 d . . .
H10 H 0.0276 0.6060 -0.0455 0.024 Uiso 1 1 calc R . .
C11 C 0.2057(6) 0.6600(7) -0.1248(4) 0.0255(9) Uani 1 1 d . . .
H11 H 0.1593 0.7759 -0.1587 0.031 Uiso 1 1 calc R . .
C12 C 0.3536(6) 0.5902(7) -0.1411(4) 0.0244(9) Uani 1 1 d . . .
H12 H 0.4114 0.6602 -0.1848 0.029 Uiso 1 1 calc R . .
C13 C 0.4162(6) 0.4193(6) -0.0937(4) 0.0208(9) Uani 1 1 d . . .
H13 H 0.5161 0.3688 -0.1056 0.025 Uiso 1 1 calc R . .
C14 C 0.3314(5) 0.3216(6) -0.0282(3) 0.0183(8) Uani 1 1 d . . .
C15 C 0.3898(5) 0.1392(6) 0.0265(3) 0.0183(8) Uani 1 1 d . . .
C16 C 0.5329(6) 0.0460(6) 0.0164(4) 0.0230(9) Uani 1 1 d . . .
H16 H 0.5984 0.1002 -0.0280 0.028 Uiso 1 1 calc R . .
C17 C 0.5801(5) -0.1245(6) 0.0707(4) 0.0255(10) Uani 1 1 d . . .
H17 H 0.6772 -0.1890 0.0635 0.031 Uiso 1 1 calc R . .
C18 C 0.4837(6) -0.2008(6) 0.1361(4) 0.0247(9) Uani 1 1 d . . .
H18 H 0.5146 -0.3168 0.1755 0.030 Uiso 1 1 calc R . .
C19 C 0.3412(5) -0.1032(7) 0.1425(4) 0.0222(9) Uani 1 1 d . . .
H19 H 0.2740 -0.1565 0.1860 0.027 Uiso 1 1 calc R . .


_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
Ru1 C1 1.895(5) . yes
Ru1 C2 1.901(5) . yes
Ru1 N2 2.116(3) . yes
Ru1 N1 2.116(3) . yes
Ru1 Br1 2.5451(5) . yes
Ru1 Br2 2.5558(6) . yes
O1 C1 1.102(5) . ?
O2 C2 1.095(6) . ?
N1 C10 1.345(5) . ?
N1 C14 1.357(5) . ?
N2 C19 1.340(6) . ?
N2 C15 1.370(5) . ?
C10 C11 1.381(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.375(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.389(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.469(6) . ?
C15 C16 1.392(6) . ?
C16 C17 1.378(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.390(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(6) . ?
C18 H18 0.9500 . ?
C19 H19 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
C1 Ru1 C2 89.40(18) . . ?
C1 Ru1 N2 95.95(16) . . ?
C2 Ru1 N2 174.62(17) . . ?
C1 Ru1 N1 173.67(16) . . ?
C2 Ru1 N1 96.93(16) . . ?
N2 Ru1 N1 77.72(14) . . ?
C1 Ru1 Br1 91.10(14) . . ?
C2 Ru1 Br1 90.10(13) . . ?
N2 Ru1 Br1 89.22(10) . . ?
N1 Ru1 Br1 88.74(10) . . ?
C1 Ru1 Br2 92.22(14) . . ?
C2 Ru1 Br2 90.74(13) . . ?
N2 Ru1 Br2 89.64(10) . . ?
N1 Ru1 Br2 87.86(10) . . ?
Br1 Ru1 Br2 176.57(2) . . ?
C10 N1 C14 118.7(4) . . ?
C10 N1 Ru1 125.7(3) . . ?
C14 N1 Ru1 115.6(3) . . ?
C19 N2 C15 118.8(4) . . ?
C19 N2 Ru1 126.2(3) . . ?
C15 N2 Ru1 115.1(3) . . ?
O1 C1 Ru1 178.9(4) . . ?
O2 C2 Ru1 178.6(4) . . ?
N1 C10 C11 122.5(4) . . ?
N1 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C10 C11 C12 118.5(4) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C13 C12 C11 119.7(4) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 119.1(4) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 121.5(4) . . ?
N1 C14 C15 115.7(3) . . ?
C13 C14 C15 122.8(4) . . ?
N2 C15 C16 120.5(4) . . ?
N2 C15 C14 115.9(3) . . ?
C16 C15 C14 123.7(4) . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 119.1(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 118.4(4) . . ?
C19 C18 H18 120.8 . . ?
C17 C18 H18 120.8 . . ?
N2 C19 C18 123.0(4) . . ?
N2 C19 H19 118.5 . . ?
C18 C19 H19 118.5 . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        30.75
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.956
_refine_diff_density_min         -0.969
_refine_diff_density_rms         0.131
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1009215'
_audit_update_record             
;
2014-06-19 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H8 I2 N2 O2 Ru'
_chemical_formula_sum            'C12 H8 I2 N2 O2 Ru'
_chemical_formula_weight         567.07

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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   13.7231(15)
_cell_length_b                   11.9220(13)
_cell_length_c                   18.0712(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2956.6(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      38.78

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.548
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2080
_exptl_absorpt_coefficient_mu    5.235
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.3018
_exptl_absorpt_correction_T_max  0.6334
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'flat graphite crystal'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_device       
'62mm x 62mm CCD camera on three-circle goniostat'
_diffrn_detector_area_resol_mean 16 # 8 for binned mode
_diffrn_measurement_method       'φ scans and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            47643
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4306
_reflns_number_gt                3666
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Diamond v.3.2f (Brandenburg, 2010)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0188P)²+4.9791P] 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         4306
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0235
_refine_ls_wR_factor_ref         0.0522
_refine_ls_wR_factor_gt          0.0490
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.467247(15) 0.124525(17) 0.189853(11) 0.01845(5) Uani 1 1 d . . .
I2 I 0.520463(14) 0.331250(16) 0.453178(11) 0.01660(5) Uani 1 1 d . . .
Ru1 Ru 0.496059(16) 0.225415(19) 0.321815(13) 0.01155(5) Uani 1 1 d . . .
O1 O 0.65952(17) 0.3497(2) 0.24826(15) 0.0263(5) Uani 1 1 d . . .
O2 O 0.35826(16) 0.40599(19) 0.27143(14) 0.0220(5) Uani 1 1 d . . .
N1 N 0.39070(17) 0.1157(2) 0.36903(14) 0.0139(5) Uani 1 1 d . . .
N2 N 0.58207(17) 0.0894(2) 0.36059(14) 0.0131(5) Uani 1 1 d . . .
C1 C 0.5985(2) 0.3058(3) 0.27696(18) 0.0178(6) Uani 1 1 d . . .
C2 C 0.4093(2) 0.3395(3) 0.29073(17) 0.0150(6) Uani 1 1 d . . .
C10 C 0.2941(2) 0.1355(3) 0.37256(18) 0.0186(6) Uani 1 1 d . . .
H10 H 0.2698 0.2049 0.3545 0.022 Uiso 1 1 calc R . .
C11 C 0.2291(2) 0.0587(3) 0.40142(19) 0.0218(7) Uani 1 1 d . . .
H11 H 0.1614 0.0754 0.4036 0.026 Uiso 1 1 calc R . .
C12 C 0.2641(2) -0.0426(3) 0.42713(18) 0.0224(7) Uani 1 1 d . . .
H12 H 0.2206 -0.0970 0.4468 0.027 Uiso 1 1 calc R . .
C13 C 0.3631(2) -0.0642(3) 0.42395(18) 0.0197(6) Uani 1 1 d . . .
H13 H 0.3883 -0.1335 0.4416 0.024 Uiso 1 1 calc R . .
C14 C 0.4252(2) 0.0164(2) 0.39466(16) 0.0144(6) Uani 1 1 d . . .
C15 C 0.5318(2) 0.0019(2) 0.39008(16) 0.0143(6) Uani 1 1 d . . .
C16 C 0.5794(2) -0.0937(3) 0.41528(18) 0.0183(6) Uani 1 1 d . . .
H16 H 0.5430 -0.1551 0.4342 0.022 Uiso 1 1 calc R . .
C17 C 0.6803(2) -0.0988(3) 0.41261(18) 0.0202(6) Uani 1 1 d . . .
H17 H 0.7138 -0.1636 0.4298 0.024 Uiso 1 1 calc R . .
C18 C 0.7312(2) -0.0088(3) 0.38470(18) 0.0193(6) Uani 1 1 d . . .
H18 H 0.8005 -0.0096 0.3835 0.023 Uiso 1 1 calc R . .
C19 C 0.6799(2) 0.0833(3) 0.35837(17) 0.0164(6) Uani 1 1 d . . .
H19 H 0.7153 0.1444 0.3380 0.020 Uiso 1 1 calc R . .


_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
I1 Ru1 2.7000(4) . yes
I2 Ru1 2.7092(4) . yes
Ru1 C1 1.885(3) . yes
Ru1 C2 1.892(3) . yes
Ru1 N2 2.124(2) . yes
Ru1 N1 2.128(2) . yes
O1 C1 1.115(4) . ?
O2 C2 1.114(4) . ?
N1 C10 1.348(4) . ?
N1 C14 1.356(4) . ?
N2 C19 1.345(4) . ?
N2 C15 1.360(4) . ?
C10 C11 1.380(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.475(4) . ?
C15 C16 1.390(4) . ?
C16 C17 1.388(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 H19 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
C1 Ru1 C2 88.63(12) . . ?
C1 Ru1 N2 96.64(11) . . ?
C2 Ru1 N2 174.72(11) . . ?
C1 Ru1 N1 172.64(11) . . ?
C2 Ru1 N1 97.65(11) . . ?
N2 Ru1 N1 77.07(10) . . ?
C1 Ru1 I1 87.48(10) . . ?
C2 Ru1 I1 88.04(9) . . ?
N2 Ru1 I1 91.88(7) . . ?
N1 Ru1 I1 88.90(7) . . ?
C1 Ru1 I2 92.74(10) . . ?
C2 Ru1 I2 90.19(9) . . ?
N2 Ru1 I2 89.87(7) . . ?
N1 Ru1 I2 91.08(7) . . ?
I1 Ru1 I2 178.206(12) . . ?
C10 N1 C14 118.6(3) . . ?
C10 N1 Ru1 125.4(2) . . ?
C14 N1 Ru1 115.86(19) . . ?
C19 N2 C15 118.4(3) . . ?
C19 N2 Ru1 125.9(2) . . ?
C15 N2 Ru1 115.65(19) . . ?
O1 C1 Ru1 177.0(3) . . ?
O2 C2 Ru1 179.0(3) . . ?
N1 C10 C11 122.5(3) . . ?
N1 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 118.8(3) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 119.3(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 121.3(3) . . ?
N1 C14 C15 115.4(3) . . ?
C13 C14 C15 123.2(3) . . ?
N2 C15 C16 121.2(3) . . ?
N2 C15 C14 115.8(3) . . ?
C16 C15 C14 123.0(3) . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 119.0(3) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
N2 C19 C18 122.7(3) . . ?
N2 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.218
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.139

#===END=========================================================================
