# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_[Ru]-1
_audit_block_doi                 10.5517/cc1j1lhn
_database_code_depnum_ccdc_archive 'CCDC 1401711'
_audit_update_record             
;
2015-05-23 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cl2 N2 O2 Ru'
_chemical_formula_weight         426.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   7.6680(5)
_cell_length_b                   8.3022(6)
_cell_length_c                   13.5405(6)
_cell_angle_alpha                83.606(5)
_cell_angle_beta                 81.922(5)
_cell_angle_gamma                70.403(6)
_cell_volume                     802.11(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3463
_cell_measurement_theta_min      6.3690
_cell_measurement_theta_max      70.9480

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424
_exptl_absorpt_coefficient_mu    11.044
_exptl_absorpt_correction_T_min  0.1215
_exptl_absorpt_correction_T_max  0.2051
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4800
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.30
_diffrn_reflns_theta_max         72.68
_reflns_number_total             3022
_reflns_number_gt                2977
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0958P)²+2.7233P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3022
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1363
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.28955(4) 0.44063(4) 0.80885(2) 0.01404(17) Uani 1 1 d . . .
Cl1 Cl 0.03697(16) 0.33245(15) 0.80209(8) 0.0209(3) Uani 1 1 d . . .
Cl2 Cl 0.67667(18) -0.14195(16) 0.78472(10) 0.0300(3) Uani 1 1 d . . .
N1 N 0.3603(6) 0.3812(5) 0.6588(3) 0.0156(8) Uani 1 1 d . . .
N2 N 0.1207(6) 0.6671(5) 0.7351(3) 0.0183(8) Uani 1 1 d . . .
H2A H -0.0007 0.6914 0.7637 0.022 Uiso 1 1 calc R . .
H2B H 0.1598 0.7574 0.7440 0.022 Uiso 1 1 calc R . .
C1 C 0.4821(7) 0.2383(6) 0.6249(4) 0.0214(10) Uani 1 1 d . . .
H1 H 0.5535 0.1559 0.6707 0.026 Uiso 1 1 calc R . .
C2 C 0.5098(8) 0.2036(7) 0.5229(4) 0.0253(11) Uani 1 1 d . . .
H2 H 0.6002 0.1004 0.5011 0.030 Uiso 1 1 calc R . .
C3 C 0.4074(8) 0.3177(7) 0.4560(4) 0.0251(11) Uani 1 1 d . . .
H3 H 0.4241 0.2938 0.3876 0.030 Uiso 1 1 calc R . .
C4 C 0.2767(7) 0.4712(7) 0.4888(4) 0.0214(10) Uani 1 1 d . . .
C5 C 0.1614(8) 0.5987(8) 0.4260(4) 0.0267(12) Uani 1 1 d . . .
H5 H 0.1707 0.5829 0.3568 0.032 Uiso 1 1 calc R . .
C6 C 0.0362(8) 0.7451(8) 0.4645(4) 0.0303(12) Uani 1 1 d . . .
H6 H -0.0401 0.8295 0.4215 0.036 Uiso 1 1 calc R . .
C7 C 0.0194(7) 0.7718(7) 0.5661(4) 0.0245(11) Uani 1 1 d . . .
H7 H -0.0675 0.8740 0.5913 0.029 Uiso 1 1 calc R . .
C8 C 0.1282(7) 0.6508(6) 0.6295(4) 0.0177(9) Uani 1 1 d . . .
C9 C 0.2579(6) 0.4995(6) 0.5916(3) 0.0166(9) Uani 1 1 d . . .
C10 C 0.2968(8) 0.3423(8) 0.9654(4) 0.0306(13) Uani 1 1 d . . .
H10 H 0.2151 0.2928 1.0072 0.037 Uiso 1 1 calc R . .
C11 C 0.2597(8) 0.5190(8) 0.9607(4) 0.0273(12) Uani 1 1 d . . .
H11 H 0.1544 0.5892 0.9996 0.033 Uiso 1 1 calc R . .
C12 C 0.3794(8) 0.5928(7) 0.8979(4) 0.0241(11) Uani 1 1 d . . .
H12 H 0.3524 0.7136 0.8932 0.029 Uiso 1 1 calc R . .
C13 C 0.5386(8) 0.4896(8) 0.8421(4) 0.0256(11) Uani 1 1 d . . .
H13 H 0.6222 0.5389 0.8019 0.031 Uiso 1 1 calc R . .
C14 C 0.5716(7) 0.3108(7) 0.8471(4) 0.0246(11) Uani 1 1 d . . .
H14 H 0.6758 0.2403 0.8076 0.029 Uiso 1 1 calc R . .
C15 C 0.4531(9) 0.2359(7) 0.9093(4) 0.0282(12) Uani 1 1 d . . .
H15 H 0.4780 0.1154 0.9134 0.034 Uiso 1 1 calc R . .
O101 O 0.2676(7) 0.9509(6) 0.7251(4) 0.0409(11) Uani 1 1 d . . .
O333 O -0.0321(19) 0.8982(17) 0.9155(10) 0.065(3) Uani 0.50 1 d P . .
O444 O -0.058(4) -0.002(2) 0.9866(16) 0.118(8) Uani 0.50 1 d P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N1 2.097(4) . ?
Ru1 N2 2.126(4) . ?
Ru1 C12 2.164(5) . ?
Ru1 C14 2.175(5) . ?
Ru1 C11 2.184(5) . ?
Ru1 C10 2.186(5) . ?
Ru1 C13 2.195(5) . ?
Ru1 C15 2.201(5) . ?
Ru1 Cl1 2.4085(11) . ?
N1 C1 1.322(7) . ?
N1 C9 1.376(6) . ?
N2 C8 1.443(6) . ?
N2 H2A 0.9200 . ?
N2 H2B 0.9200 . ?
C1 C2 1.415(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.358(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(8) . ?
C4 C9 1.418(7) . ?
C5 C6 1.374(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(7) . ?
C10 C11 1.393(9) . ?
C10 C15 1.406(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.409(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.407(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.415(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.403(8) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
O333 O444 1.29(2) 1_565 ?
O444 O444 1.02(4) 2_557 ?
O444 O333 1.29(2) 1_545 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 N2 78.66(16) . . ?
N1 Ru1 C12 132.07(18) . . ?
N2 Ru1 C12 90.49(18) . . ?
N1 Ru1 C14 93.31(18) . . ?
N2 Ru1 C14 142.72(19) . . ?
C12 Ru1 C14 68.0(2) . . ?
N1 Ru1 C11 169.56(19) . . ?
N2 Ru1 C11 101.73(19) . . ?
C12 Ru1 C11 37.8(2) . . ?
C14 Ru1 C11 80.0(2) . . ?
N1 Ru1 C10 146.3(2) . . ?
N2 Ru1 C10 133.4(2) . . ?
C12 Ru1 C10 67.6(2) . . ?
C14 Ru1 C10 67.3(2) . . ?
C11 Ru1 C10 37.2(2) . . ?
N1 Ru1 C13 101.89(18) . . ?
N2 Ru1 C13 107.85(19) . . ?
C12 Ru1 C13 37.6(2) . . ?
C14 Ru1 C13 37.8(2) . . ?
C11 Ru1 C13 67.9(2) . . ?
C10 Ru1 C13 79.9(2) . . ?
N1 Ru1 C15 111.7(2) . . ?
N2 Ru1 C15 169.24(19) . . ?
C12 Ru1 C15 80.3(2) . . ?
C14 Ru1 C15 37.4(2) . . ?
C11 Ru1 C15 67.6(2) . . ?
C10 Ru1 C15 37.4(2) . . ?
C13 Ru1 C15 67.9(2) . . ?
N1 Ru1 Cl1 84.43(11) . . ?
N2 Ru1 Cl1 84.98(12) . . ?
C12 Ru1 Cl1 141.50(15) . . ?
C14 Ru1 Cl1 130.87(15) . . ?
C11 Ru1 Cl1 106.01(16) . . ?
C10 Ru1 Cl1 88.22(14) . . ?
C13 Ru1 Cl1 166.50(15) . . ?
C15 Ru1 Cl1 98.73(15) . . ?
C1 N1 C9 118.2(4) . . ?
C1 N1 Ru1 126.4(3) . . ?
C9 N1 Ru1 115.2(3) . . ?
C8 N2 Ru1 112.2(3) . . ?
C8 N2 H2A 109.2 . . ?
Ru1 N2 H2A 109.2 . . ?
C8 N2 H2B 109.2 . . ?
Ru1 N2 H2B 109.2 . . ?
H2A N2 H2B 107.9 . . ?
N1 C1 C2 122.4(5) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.4(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 124.3(5) . . ?
C3 C4 C9 117.7(5) . . ?
C5 C4 C9 118.0(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C8 C7 C6 120.3(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 119.8(5) . . ?
C7 C8 N2 124.2(5) . . ?
C9 C8 N2 116.1(4) . . ?
N1 C9 C8 117.3(4) . . ?
N1 C9 C4 122.2(4) . . ?
C8 C9 C4 120.5(4) . . ?
C11 C10 C15 121.2(5) . . ?
C11 C10 Ru1 71.3(3) . . ?
C15 C10 Ru1 71.9(3) . . ?
C11 C10 H10 119.4 . . ?
C15 C10 H10 119.4 . . ?
Ru1 C10 H10 129.9 . . ?
C10 C11 C12 119.5(5) . . ?
C10 C11 Ru1 71.5(3) . . ?
C12 C11 Ru1 70.3(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
Ru1 C11 H11 130.5 . . ?
C13 C12 C11 120.7(5) . . ?
C13 C12 Ru1 72.4(3) . . ?
C11 C12 Ru1 71.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
Ru1 C12 H12 128.3 . . ?
C12 C13 C14 118.6(5) . . ?
C12 C13 Ru1 70.0(3) . . ?
C14 C13 Ru1 70.4(3) . . ?
C12 C13 H13 120.7 . . ?
C14 C13 H13 120.7 . . ?
Ru1 C13 H13 131.6 . . ?
C15 C14 C13 121.2(5) . . ?
C15 C14 Ru1 72.3(3) . . ?
C13 C14 Ru1 71.9(3) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
Ru1 C14 H14 128.8 . . ?
C14 C15 C10 118.8(5) . . ?
C14 C15 Ru1 70.3(3) . . ?
C10 C15 Ru1 70.7(3) . . ?
C14 C15 H15 120.6 . . ?
C10 C15 H15 120.6 . . ?
Ru1 C15 H15 130.9 . . ?
O444 O444 O333 117(4) 2_557 1_545 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ru1 N1 C1 179.0(4) . . . . ?
C12 Ru1 N1 C1 98.7(4) . . . . ?
C14 Ru1 N1 C1 35.7(4) . . . . ?
C11 Ru1 N1 C1 85.8(11) . . . . ?
C10 Ru1 N1 C1 -16.8(6) . . . . ?
C13 Ru1 N1 C1 72.9(4) . . . . ?
C15 Ru1 N1 C1 2.2(4) . . . . ?
Cl1 Ru1 N1 C1 -95.0(4) . . . . ?
N2 Ru1 N1 C9 -6.1(3) . . . . ?
C12 Ru1 N1 C9 -86.3(4) . . . . ?
C14 Ru1 N1 C9 -149.3(3) . . . . ?
C11 Ru1 N1 C9 -99.2(10) . . . . ?
C10 Ru1 N1 C9 158.2(3) . . . . ?
C13 Ru1 N1 C9 -112.1(3) . . . . ?
C15 Ru1 N1 C9 177.1(3) . . . . ?
Cl1 Ru1 N1 C9 79.9(3) . . . . ?
N1 Ru1 N2 C8 6.7(3) . . . . ?
C12 Ru1 N2 C8 139.6(3) . . . . ?
C14 Ru1 N2 C8 87.1(4) . . . . ?
C11 Ru1 N2 C8 176.0(3) . . . . ?
C10 Ru1 N2 C8 -161.4(3) . . . . ?
C13 Ru1 N2 C8 105.6(3) . . . . ?
C15 Ru1 N2 C8 170.6(9) . . . . ?
Cl1 Ru1 N2 C8 -78.7(3) . . . . ?
C9 N1 C1 C2 -0.1(7) . . . . ?
Ru1 N1 C1 C2 174.8(3) . . . . ?
N1 C1 C2 C3 -1.1(7) . . . . ?
C1 C2 C3 C4 1.2(7) . . . . ?
C2 C3 C4 C5 -179.5(5) . . . . ?
C2 C3 C4 C9 -0.1(7) . . . . ?
C3 C4 C5 C6 179.7(5) . . . . ?
C9 C4 C5 C6 0.2(7) . . . . ?
C4 C5 C6 C7 0.0(8) . . . . ?
C5 C6 C7 C8 -0.3(8) . . . . ?
C6 C7 C8 C9 0.3(7) . . . . ?
C6 C7 C8 N2 180.0(4) . . . . ?
Ru1 N2 C8 C7 173.7(4) . . . . ?
Ru1 N2 C8 C9 -6.6(5) . . . . ?
C1 N1 C9 C8 179.8(4) . . . . ?
Ru1 N1 C9 C8 4.3(5) . . . . ?
C1 N1 C9 C4 1.2(6) . . . . ?
Ru1 N1 C9 C4 -174.2(3) . . . . ?
C7 C8 C9 N1 -178.7(4) . . . . ?
N2 C8 C9 N1 1.7(6) . . . . ?
C7 C8 C9 C4 -0.1(7) . . . . ?
N2 C8 C9 C4 -179.8(4) . . . . ?
C3 C4 C9 N1 -1.2(7) . . . . ?
C5 C4 C9 N1 178.3(4) . . . . ?
C3 C4 C9 C8 -179.6(4) . . . . ?
C5 C4 C9 C8 -0.2(6) . . . . ?
N1 Ru1 C10 C11 163.0(3) . . . . ?
N2 Ru1 C10 C11 -38.5(4) . . . . ?
C12 Ru1 C10 C11 29.4(3) . . . . ?
C14 Ru1 C10 C11 103.9(4) . . . . ?
C13 Ru1 C10 C11 66.6(4) . . . . ?
C15 Ru1 C10 C11 133.2(5) . . . . ?
Cl1 Ru1 C10 C11 -119.9(3) . . . . ?
N1 Ru1 C10 C15 29.7(5) . . . . ?
N2 Ru1 C10 C15 -171.7(3) . . . . ?
C12 Ru1 C10 C15 -103.8(4) . . . . ?
C14 Ru1 C10 C15 -29.3(3) . . . . ?
C11 Ru1 C10 C15 -133.2(5) . . . . ?
C13 Ru1 C10 C15 -66.6(3) . . . . ?
Cl1 Ru1 C10 C15 106.9(3) . . . . ?
C15 C10 C11 C12 0.7(8) . . . . ?
Ru1 C10 C11 C12 -53.3(4) . . . . ?
C15 C10 C11 Ru1 54.0(5) . . . . ?
N1 Ru1 C11 C10 -116.5(10) . . . . ?
N2 Ru1 C11 C10 152.5(3) . . . . ?
C12 Ru1 C11 C10 -132.2(5) . . . . ?
C14 Ru1 C11 C10 -65.4(3) . . . . ?
C13 Ru1 C11 C10 -102.8(4) . . . . ?
C15 Ru1 C11 C10 -28.6(3) . . . . ?
Cl1 Ru1 C11 C10 64.4(3) . . . . ?
N1 Ru1 C11 C12 15.7(12) . . . . ?
N2 Ru1 C11 C12 -75.3(3) . . . . ?
C14 Ru1 C11 C12 66.7(3) . . . . ?
C10 Ru1 C11 C12 132.2(5) . . . . ?
C13 Ru1 C11 C12 29.4(3) . . . . ?
C15 Ru1 C11 C12 103.6(4) . . . . ?
Cl1 Ru1 C11 C12 -163.4(3) . . . . ?
C10 C11 C12 C13 -1.8(7) . . . . ?
Ru1 C11 C12 C13 -55.6(4) . . . . ?
C10 C11 C12 Ru1 53.8(4) . . . . ?
N1 Ru1 C12 C13 -44.3(4) . . . . ?
N2 Ru1 C12 C13 -119.4(3) . . . . ?
C14 Ru1 C12 C13 29.4(3) . . . . ?
C11 Ru1 C12 C13 131.9(5) . . . . ?
C10 Ru1 C12 C13 102.9(4) . . . . ?
C15 Ru1 C12 C13 66.2(3) . . . . ?
Cl1 Ru1 C12 C13 158.1(3) . . . . ?
N1 Ru1 C12 C11 -176.2(3) . . . . ?
N2 Ru1 C12 C11 108.7(3) . . . . ?
C14 Ru1 C12 C11 -102.5(4) . . . . ?
C10 Ru1 C12 C11 -29.0(3) . . . . ?
C13 Ru1 C12 C11 -131.9(5) . . . . ?
C15 Ru1 C12 C11 -65.7(4) . . . . ?
Cl1 Ru1 C12 C11 26.2(4) . . . . ?
C11 C12 C13 C14 2.7(7) . . . . ?
Ru1 C12 C13 C14 -52.7(4) . . . . ?
C11 C12 C13 Ru1 55.4(4) . . . . ?
N1 Ru1 C13 C12 148.0(3) . . . . ?
N2 Ru1 C13 C12 66.2(3) . . . . ?
C14 Ru1 C13 C12 -132.1(5) . . . . ?
C11 Ru1 C13 C12 -29.5(3) . . . . ?
C10 Ru1 C13 C12 -66.3(3) . . . . ?
C15 Ru1 C13 C12 -103.2(3) . . . . ?
Cl1 Ru1 C13 C12 -95.1(7) . . . . ?
N1 Ru1 C13 C14 -79.9(3) . . . . ?
N2 Ru1 C13 C14 -161.7(3) . . . . ?
C12 Ru1 C13 C14 132.1(5) . . . . ?
C11 Ru1 C13 C14 102.6(3) . . . . ?
C10 Ru1 C13 C14 65.8(3) . . . . ?
C15 Ru1 C13 C14 28.9(3) . . . . ?
Cl1 Ru1 C13 C14 37.0(8) . . . . ?
C12 C13 C14 C15 -2.6(7) . . . . ?
Ru1 C13 C14 C15 -55.1(4) . . . . ?
C12 C13 C14 Ru1 52.5(4) . . . . ?
N1 Ru1 C14 C15 -122.2(3) . . . . ?
N2 Ru1 C14 C15 162.2(3) . . . . ?
C12 Ru1 C14 C15 103.3(4) . . . . ?
C11 Ru1 C14 C15 65.9(3) . . . . ?
C10 Ru1 C14 C15 29.3(3) . . . . ?
C13 Ru1 C14 C15 132.6(5) . . . . ?
Cl1 Ru1 C14 C15 -36.7(4) . . . . ?
N1 Ru1 C14 C13 105.2(3) . . . . ?
N2 Ru1 C14 C13 29.6(5) . . . . ?
C12 Ru1 C14 C13 -29.3(3) . . . . ?
C11 Ru1 C14 C13 -66.7(3) . . . . ?
C10 Ru1 C14 C13 -103.2(3) . . . . ?
C15 Ru1 C14 C13 -132.6(5) . . . . ?
Cl1 Ru1 C14 C13 -169.3(2) . . . . ?
C13 C14 C15 C10 1.5(7) . . . . ?
Ru1 C14 C15 C10 -53.3(4) . . . . ?
C13 C14 C15 Ru1 54.9(4) . . . . ?
C11 C10 C15 C14 -0.6(8) . . . . ?
Ru1 C10 C15 C14 53.1(4) . . . . ?
C11 C10 C15 Ru1 -53.8(5) . . . . ?
N1 Ru1 C15 C14 65.3(3) . . . . ?
N2 Ru1 C15 C14 -97.7(10) . . . . ?
C12 Ru1 C15 C14 -66.2(3) . . . . ?
C11 Ru1 C15 C14 -103.4(4) . . . . ?
C10 Ru1 C15 C14 -131.9(5) . . . . ?
C13 Ru1 C15 C14 -29.1(3) . . . . ?
Cl1 Ru1 C15 C14 152.8(3) . . . . ?
N1 Ru1 C15 C10 -162.8(3) . . . . ?
N2 Ru1 C15 C10 34.2(11) . . . . ?
C12 Ru1 C15 C10 65.6(3) . . . . ?
C14 Ru1 C15 C10 131.9(5) . . . . ?
C11 Ru1 C15 C10 28.5(3) . . . . ?
C13 Ru1 C15 C10 102.7(4) . . . . ?
Cl1 Ru1 C15 C10 -75.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.946
_diffrn_reflns_theta_full        72.68
_diffrn_measured_fraction_theta_full 0.946
_refine_diff_density_max         1.468
_refine_diff_density_min         -1.228
_refine_diff_density_rms         0.222
####################################################################### 
# 
# 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_[Ru]-2
_database_code_depnum_ccdc_archive 'CCDC 1402536'
_audit_update_record             
;
2015-05-23 deposited with the CCDC.
2015-08-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 Cl2 N2 Ru'
_chemical_formula_weight         450.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 '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/c'

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

_cell_length_a                   17.0720(2)
_cell_length_b                   12.30860(10)
_cell_length_c                   9.10130(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.9000(10)
_cell_angle_gamma                90.00
_cell_volume                     1877.97(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9074
_cell_measurement_theta_min      4.4570
_cell_measurement_theta_max      71.1700

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    9.382
_exptl_absorpt_correction_T_min  0.1478
_exptl_absorpt_correction_T_max  0.2433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Micro-Focus (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11844
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0152
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.46
_diffrn_reflns_theta_max         71.35
_reflns_number_total             3586
_reflns_number_gt                3518
_reflns_threshold_expression     >2sigma(I)

_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0464P)²+1.2081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3586
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0709
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.223444(9) 0.023348(12) 0.864330(16) 0.02117(8) Uani 1 1 d . . .
Cl1 Cl 0.20352(4) 0.11335(5) 0.62644(6) 0.03895(15) Uani 1 1 d . . .
Cl2 Cl 0.31244(4) -0.30614(5) 0.93367(8) 0.04486(16) Uani 1 1 d . . .
N1 N 0.32747(11) 0.11676(15) 0.9175(2) 0.0247(4) Uani 1 1 d . . .
N2 N 0.30598(11) -0.07387(16) 0.7729(2) 0.0259(4) Uani 1 1 d . . .
C1 C 0.33467(15) 0.21148(19) 0.9881(3) 0.0328(5) Uani 1 1 d . . .
H1 H 0.2889 0.2418 1.0179 0.039 Uiso 1 1 calc R . .
C2 C 0.40711(17) 0.2691(2) 1.0207(3) 0.0385(6) Uani 1 1 d . . .
H2 H 0.4100 0.3361 1.0734 0.046 Uiso 1 1 calc R . .
C3 C 0.47296(15) 0.2284(2) 0.9766(3) 0.0376(6) Uani 1 1 d . . .
H3 H 0.5226 0.2651 1.0018 0.045 Uiso 1 1 calc R . .
C4 C 0.46708(14) 0.1311(2) 0.8929(3) 0.0315(5) Uani 1 1 d . . .
C5 C 0.52978(15) 0.0869(3) 0.8301(3) 0.0420(6) Uani 1 1 d . . .
H5 H 0.5804 0.1216 0.8460 0.050 Uiso 1 1 calc R . .
C6 C 0.51741(17) -0.0056(3) 0.7467(4) 0.0478(7) Uani 1 1 d . . .
H6 H 0.5590 -0.0327 0.7007 0.057 Uiso 1 1 calc R . .
C7 C 0.44417(16) -0.0620(2) 0.7273(3) 0.0396(6) Uani 1 1 d . . .
H7 H 0.4374 -0.1279 0.6721 0.048 Uiso 1 1 calc R . .
C8 C 0.38331(14) -0.02152(17) 0.7880(3) 0.0266(5) Uani 1 1 d . . .
C9 C 0.39306(13) 0.07659(18) 0.8681(2) 0.0254(4) Uani 1 1 d . . .
C10 C 0.25510(19) 0.0656(3) 1.2396(3) 0.0480(7) Uani 1 1 d . . .
H10A H 0.2237 0.0699 1.3191 0.072 Uiso 1 1 calc R . .
H10B H 0.2760 0.1377 1.2227 0.072 Uiso 1 1 calc R . .
H10C H 0.2996 0.0149 1.2693 0.072 Uiso 1 1 calc R . .
C11 C 0.20309(15) 0.02626(19) 1.0984(3) 0.0307(5) Uani 1 1 d . . .
C12 C 0.14886(14) 0.0977(2) 1.0084(3) 0.0322(5) Uani 1 1 d . . .
H12 H 0.1452 0.1712 1.0379 0.039 Uiso 1 1 calc R . .
C13 C 0.10059(13) 0.0601(2) 0.8758(3) 0.0329(5) Uani 1 1 d . . .
H13 H 0.0647 0.1092 0.8169 0.039 Uiso 1 1 calc R . .
C14 C 0.10383(13) -0.0496(2) 0.8270(3) 0.0308(5) Uani 1 1 d . . .
C15 C 0.15879(14) -0.11861(19) 0.9156(3) 0.0309(5) Uani 1 1 d . . .
H15 H 0.1634 -0.1917 0.8848 0.037 Uiso 1 1 calc R . .
C16 C 0.20770(14) -0.0819(2) 1.0504(3) 0.0311(5) Uani 1 1 d . . .
H16 H 0.2439 -0.1309 1.1087 0.037 Uiso 1 1 calc R . .
C17 C 0.05039(16) -0.0844(3) 0.6827(3) 0.0442(6) Uani 1 1 d . . .
H17 H 0.0435 -0.0200 0.6145 0.053 Uiso 1 1 calc R . .
C18 C -0.0310(2) -0.1130(4) 0.7137(4) 0.0828(14) Uani 1 1 d . . .
H18A H -0.0261 -0.1738 0.7844 0.124 Uiso 1 1 calc R . .
H18B H -0.0662 -0.1340 0.6200 0.124 Uiso 1 1 calc R . .
H18C H -0.0535 -0.0500 0.7567 0.124 Uiso 1 1 calc R . .
C19 C 0.0842(3) -0.1751(5) 0.6020(5) 0.1011(19) Uani 1 1 d . . .
H19A H 0.1377 -0.1550 0.5871 0.152 Uiso 1 1 calc R . .
H19B H 0.0495 -0.1875 0.5047 0.152 Uiso 1 1 calc R . .
H19C H 0.0874 -0.2416 0.6620 0.152 Uiso 1 1 calc R . .
H1N H 0.310(2) -0.140(3) 0.819(4) 0.050(9) Uiso 1 1 d . . .
H2N H 0.291(2) -0.081(3) 0.670(4) 0.052(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N1 2.0940(18) . ?
Ru1 N2 2.1336(18) . ?
Ru1 C15 2.164(2) . ?
Ru1 C13 2.167(2) . ?
Ru1 C16 2.189(2) . ?
Ru1 C12 2.193(2) . ?
Ru1 C14 2.198(2) . ?
Ru1 C11 2.223(2) . ?
Ru1 Cl1 2.3984(6) . ?
N1 C1 1.325(3) . ?
N1 C9 1.375(3) . ?
N2 C8 1.452(3) . ?
N2 H1N 0.91(4) . ?
N2 H2N 0.93(4) . ?
C1 C2 1.408(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.359(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.412(4) . ?
C3 H3 0.9500 . ?
C4 C9 1.411(3) . ?
C4 C5 1.414(4) . ?
C5 C6 1.362(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.360(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.404(3) . ?
C10 C11 1.498(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.408(4) . ?
C11 C12 1.419(4) . ?
C12 C13 1.405(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.426(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.402(4) . ?
C14 C17 1.512(3) . ?
C15 C16 1.421(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C19 1.509(5) . ?
C17 C18 1.511(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 N2 78.71(7) . . ?
N1 Ru1 C15 146.96(8) . . ?
N2 Ru1 C15 91.87(8) . . ?
N1 Ru1 C13 131.34(9) . . ?
N2 Ru1 C13 148.45(9) . . ?
C15 Ru1 C13 67.69(9) . . ?
N1 Ru1 C16 111.66(8) . . ?
N2 Ru1 C16 98.99(9) . . ?
C15 Ru1 C16 38.09(9) . . ?
C13 Ru1 C16 79.91(9) . . ?
N1 Ru1 C12 101.29(8) . . ?
N2 Ru1 C12 165.47(9) . . ?
C15 Ru1 C12 80.23(9) . . ?
C13 Ru1 C12 37.58(10) . . ?
C16 Ru1 C12 67.31(9) . . ?
N1 Ru1 C14 169.35(8) . . ?
N2 Ru1 C14 111.92(8) . . ?
C15 Ru1 C14 37.49(9) . . ?
C13 Ru1 C14 38.12(9) . . ?
C16 Ru1 C14 68.36(9) . . ?
C12 Ru1 C14 68.61(9) . . ?
N1 Ru1 C11 92.81(8) . . ?
N2 Ru1 C11 128.11(9) . . ?
C15 Ru1 C11 68.15(9) . . ?
C13 Ru1 C11 67.82(9) . . ?
C16 Ru1 C11 37.23(9) . . ?
C12 Ru1 C11 37.49(9) . . ?
C14 Ru1 C11 81.13(9) . . ?
N1 Ru1 Cl1 85.66(5) . . ?
N2 Ru1 Cl1 84.18(6) . . ?
C15 Ru1 Cl1 125.21(7) . . ?
C13 Ru1 Cl1 88.49(7) . . ?
C16 Ru1 Cl1 162.68(7) . . ?
C12 Ru1 Cl1 110.35(7) . . ?
C14 Ru1 Cl1 94.59(7) . . ?
C11 Ru1 Cl1 146.78(7) . . ?
C1 N1 C9 117.90(19) . . ?
C1 N1 Ru1 126.28(16) . . ?
C9 N1 Ru1 115.76(14) . . ?
C8 N2 Ru1 111.72(13) . . ?
C8 N2 H1N 111(2) . . ?
Ru1 N2 H1N 109(2) . . ?
C8 N2 H2N 102(2) . . ?
Ru1 N2 H2N 112(2) . . ?
H1N N2 H2N 111(3) . . ?
N1 C1 C2 122.9(2) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C9 C4 C3 117.4(2) . . ?
C9 C4 C5 118.4(2) . . ?
C3 C4 C5 124.2(2) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 N2 123.4(2) . . ?
C9 C8 N2 116.54(19) . . ?
N1 C9 C8 117.07(19) . . ?
N1 C9 C4 122.5(2) . . ?
C8 C9 C4 120.4(2) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C11 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 118.4(2) . . ?
C16 C11 C10 120.9(2) . . ?
C12 C11 C10 120.7(2) . . ?
C16 C11 Ru1 70.09(13) . . ?
C12 C11 Ru1 70.12(13) . . ?
C10 C11 Ru1 130.76(18) . . ?
C13 C12 C11 120.3(2) . . ?
C13 C12 Ru1 70.22(13) . . ?
C11 C12 Ru1 72.39(13) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
Ru1 C12 H12 130.1 . . ?
C12 C13 C14 121.9(2) . . ?
C12 C13 Ru1 72.19(13) . . ?
C14 C13 Ru1 72.09(13) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 H13 119.0 . . ?
Ru1 C13 H13 129.2 . . ?
C15 C14 C13 117.1(2) . . ?
C15 C14 C17 123.8(2) . . ?
C13 C14 C17 119.1(2) . . ?
C15 C14 Ru1 69.97(13) . . ?
C13 C14 Ru1 69.79(13) . . ?
C17 C14 Ru1 129.82(17) . . ?
C14 C15 C16 121.6(2) . . ?
C14 C15 Ru1 72.54(13) . . ?
C16 C15 Ru1 71.90(13) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
Ru1 C15 H15 128.8 . . ?
C11 C16 C15 120.7(2) . . ?
C11 C16 Ru1 72.68(14) . . ?
C15 C16 Ru1 70.01(13) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
Ru1 C16 H16 130.2 . . ?
C19 C17 C18 111.6(3) . . ?
C19 C17 C14 114.1(3) . . ?
C18 C17 C14 109.2(2) . . ?
C19 C17 H17 107.2 . . ?
C18 C17 H17 107.2 . . ?
C14 C17 H17 107.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 Ru1 N1 C1 179.2(2) . . . . ?
C15 Ru1 N1 C1 -105.0(2) . . . . ?
C13 Ru1 N1 C1 10.1(2) . . . . ?
C16 Ru1 N1 C1 -85.5(2) . . . . ?
C12 Ru1 N1 C1 -15.6(2) . . . . ?
C14 Ru1 N1 C1 2.5(5) . . . . ?
C11 Ru1 N1 C1 -52.5(2) . . . . ?
Cl1 Ru1 N1 C1 94.29(18) . . . . ?
N2 Ru1 N1 C9 2.01(15) . . . . ?
C15 Ru1 N1 C9 77.8(2) . . . . ?
C13 Ru1 N1 C9 -167.06(15) . . . . ?
C16 Ru1 N1 C9 97.30(16) . . . . ?
C12 Ru1 N1 C9 167.18(15) . . . . ?
C14 Ru1 N1 C9 -174.7(4) . . . . ?
C11 Ru1 N1 C9 130.34(16) . . . . ?
Cl1 Ru1 N1 C9 -82.91(15) . . . . ?
N1 Ru1 N2 C8 -3.63(15) . . . . ?
C15 Ru1 N2 C8 -151.70(16) . . . . ?
C13 Ru1 N2 C8 160.58(17) . . . . ?
C16 Ru1 N2 C8 -114.08(16) . . . . ?
C12 Ru1 N2 C8 -95.1(3) . . . . ?
C14 Ru1 N2 C8 175.72(15) . . . . ?
C11 Ru1 N2 C8 -88.30(17) . . . . ?
Cl1 Ru1 N2 C8 83.10(15) . . . . ?
C9 N1 C1 C2 -3.3(3) . . . . ?
Ru1 N1 C1 C2 179.52(18) . . . . ?
N1 C1 C2 C3 1.3(4) . . . . ?
C1 C2 C3 C4 2.7(4) . . . . ?
C2 C3 C4 C9 -4.3(3) . . . . ?
C2 C3 C4 C5 174.1(2) . . . . ?
C9 C4 C5 C6 0.7(4) . . . . ?
C3 C4 C5 C6 -177.8(3) . . . . ?
C4 C5 C6 C7 -3.2(5) . . . . ?
C5 C6 C7 C8 2.5(5) . . . . ?
C6 C7 C8 C9 0.7(4) . . . . ?
C6 C7 C8 N2 179.7(3) . . . . ?
Ru1 N2 C8 C7 -174.1(2) . . . . ?
Ru1 N2 C8 C9 4.9(2) . . . . ?
C1 N1 C9 C8 -177.3(2) . . . . ?
Ru1 N1 C9 C8 0.1(3) . . . . ?
C1 N1 C9 C4 1.4(3) . . . . ?
Ru1 N1 C9 C4 178.90(16) . . . . ?
C7 C8 C9 N1 175.6(2) . . . . ?
N2 C8 C9 N1 -3.5(3) . . . . ?
C7 C8 C9 C4 -3.2(4) . . . . ?
N2 C8 C9 C4 177.7(2) . . . . ?
C3 C4 C9 N1 2.3(3) . . . . ?
C5 C4 C9 N1 -176.2(2) . . . . ?
C3 C4 C9 C8 -178.9(2) . . . . ?
C5 C4 C9 C8 2.5(3) . . . . ?
N1 Ru1 C11 C16 -123.11(14) . . . . ?
N2 Ru1 C11 C16 -45.26(17) . . . . ?
C15 Ru1 C11 C16 29.09(14) . . . . ?
C13 Ru1 C11 C16 102.94(16) . . . . ?
C12 Ru1 C11 C16 131.9(2) . . . . ?
C14 Ru1 C11 C16 65.71(15) . . . . ?
Cl1 Ru1 C11 C16 150.52(12) . . . . ?
N1 Ru1 C11 C12 104.95(14) . . . . ?
N2 Ru1 C11 C12 -177.20(13) . . . . ?
C15 Ru1 C11 C12 -102.85(16) . . . . ?
C13 Ru1 C11 C12 -29.01(14) . . . . ?
C16 Ru1 C11 C12 -131.9(2) . . . . ?
C14 Ru1 C11 C12 -66.24(15) . . . . ?
Cl1 Ru1 C11 C12 18.6(2) . . . . ?
N1 Ru1 C11 C10 -9.0(3) . . . . ?
N2 Ru1 C11 C10 68.8(3) . . . . ?
C15 Ru1 C11 C10 143.2(3) . . . . ?
C13 Ru1 C11 C10 -143.0(3) . . . . ?
C16 Ru1 C11 C10 114.1(3) . . . . ?
C12 Ru1 C11 C10 -114.0(3) . . . . ?
C14 Ru1 C11 C10 179.8(3) . . . . ?
Cl1 Ru1 C11 C10 -95.4(3) . . . . ?
C16 C11 C12 C13 0.7(3) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
Ru1 C11 C12 C13 53.37(19) . . . . ?
C16 C11 C12 Ru1 -52.64(19) . . . . ?
C10 C11 C12 Ru1 126.3(2) . . . . ?
N1 Ru1 C12 C13 147.66(14) . . . . ?
N2 Ru1 C12 C13 -123.8(3) . . . . ?
C15 Ru1 C12 C13 -65.93(15) . . . . ?
C16 Ru1 C12 C13 -103.40(16) . . . . ?
C14 Ru1 C12 C13 -28.80(15) . . . . ?
C11 Ru1 C12 C13 -132.6(2) . . . . ?
Cl1 Ru1 C12 C13 58.13(15) . . . . ?
N1 Ru1 C12 C11 -79.74(14) . . . . ?
N2 Ru1 C12 C11 8.8(4) . . . . ?
C15 Ru1 C12 C11 66.67(14) . . . . ?
C13 Ru1 C12 C11 132.6(2) . . . . ?
C16 Ru1 C12 C11 29.19(14) . . . . ?
C14 Ru1 C12 C11 103.80(15) . . . . ?
Cl1 Ru1 C12 C11 -169.27(12) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
Ru1 C12 C13 C14 54.5(2) . . . . ?
C11 C12 C13 Ru1 -54.4(2) . . . . ?
N1 Ru1 C13 C12 -44.32(19) . . . . ?
N2 Ru1 C13 C12 156.50(16) . . . . ?
C15 Ru1 C13 C12 103.44(16) . . . . ?
C16 Ru1 C13 C12 65.73(15) . . . . ?
C14 Ru1 C13 C12 133.4(2) . . . . ?
C11 Ru1 C13 C12 28.94(14) . . . . ?
Cl1 Ru1 C13 C12 -127.20(14) . . . . ?
N1 Ru1 C13 C14 -177.72(12) . . . . ?
N2 Ru1 C13 C14 23.1(2) . . . . ?
C15 Ru1 C13 C14 -29.96(14) . . . . ?
C16 Ru1 C13 C14 -67.68(15) . . . . ?
C12 Ru1 C13 C14 -133.4(2) . . . . ?
C11 Ru1 C13 C14 -104.47(16) . . . . ?
Cl1 Ru1 C13 C14 99.40(14) . . . . ?
C12 C13 C14 C15 -1.3(3) . . . . ?
Ru1 C13 C14 C15 53.24(19) . . . . ?
C12 C13 C14 C17 -179.7(2) . . . . ?
Ru1 C13 C14 C17 -125.2(2) . . . . ?
C12 C13 C14 Ru1 -54.6(2) . . . . ?
N1 Ru1 C14 C15 -121.3(4) . . . . ?
N2 Ru1 C14 C15 62.17(15) . . . . ?
C13 Ru1 C14 C15 -130.6(2) . . . . ?
C16 Ru1 C14 C15 -29.07(14) . . . . ?
C12 Ru1 C14 C15 -102.19(16) . . . . ?
C11 Ru1 C14 C15 -65.45(15) . . . . ?
Cl1 Ru1 C14 C15 147.73(13) . . . . ?
N1 Ru1 C14 C13 9.3(5) . . . . ?
N2 Ru1 C14 C13 -167.22(14) . . . . ?
C15 Ru1 C14 C13 130.6(2) . . . . ?
C16 Ru1 C14 C13 101.54(16) . . . . ?
C12 Ru1 C14 C13 28.42(14) . . . . ?
C11 Ru1 C14 C13 65.16(15) . . . . ?
Cl1 Ru1 C14 C13 -81.66(14) . . . . ?
N1 Ru1 C14 C17 120.8(4) . . . . ?
N2 Ru1 C14 C17 -55.7(3) . . . . ?
C15 Ru1 C14 C17 -117.8(3) . . . . ?
C13 Ru1 C14 C17 111.6(3) . . . . ?
C16 Ru1 C14 C17 -146.9(3) . . . . ?
C12 Ru1 C14 C17 140.0(3) . . . . ?
C11 Ru1 C14 C17 176.7(3) . . . . ?
Cl1 Ru1 C14 C17 29.9(3) . . . . ?
C13 C14 C15 C16 1.7(3) . . . . ?
C17 C14 C15 C16 180.0(2) . . . . ?
Ru1 C14 C15 C16 54.8(2) . . . . ?
C13 C14 C15 Ru1 -53.15(19) . . . . ?
C17 C14 C15 Ru1 125.2(2) . . . . ?
N1 Ru1 C15 C14 163.17(14) . . . . ?
N2 Ru1 C15 C14 -124.83(14) . . . . ?
C13 Ru1 C15 C14 30.44(14) . . . . ?
C16 Ru1 C15 C14 132.9(2) . . . . ?
C12 Ru1 C15 C14 67.44(15) . . . . ?
C11 Ru1 C15 C14 104.46(16) . . . . ?
Cl1 Ru1 C15 C14 -40.64(16) . . . . ?
N1 Ru1 C15 C16 30.2(2) . . . . ?
N2 Ru1 C15 C16 102.23(14) . . . . ?
C13 Ru1 C15 C16 -102.50(16) . . . . ?
C12 Ru1 C15 C16 -65.49(15) . . . . ?
C14 Ru1 C15 C16 -132.9(2) . . . . ?
C11 Ru1 C15 C16 -28.48(14) . . . . ?
Cl1 Ru1 C15 C16 -173.58(11) . . . . ?
C12 C11 C16 C15 -0.4(3) . . . . ?
C10 C11 C16 C15 -179.4(2) . . . . ?
Ru1 C11 C16 C15 -53.05(19) . . . . ?
C12 C11 C16 Ru1 52.65(19) . . . . ?
C10 C11 C16 Ru1 -126.3(2) . . . . ?
C14 C15 C16 C11 -0.8(3) . . . . ?
Ru1 C15 C16 C11 54.3(2) . . . . ?
C14 C15 C16 Ru1 -55.1(2) . . . . ?
N1 Ru1 C16 C11 64.19(15) . . . . ?
N2 Ru1 C16 C11 145.54(14) . . . . ?
C15 Ru1 C16 C11 -133.0(2) . . . . ?
C13 Ru1 C16 C11 -66.44(15) . . . . ?
C12 Ru1 C16 C11 -29.38(14) . . . . ?
C14 Ru1 C16 C11 -104.35(16) . . . . ?
Cl1 Ru1 C16 C11 -115.1(2) . . . . ?
N1 Ru1 C16 C15 -162.82(13) . . . . ?
N2 Ru1 C16 C15 -81.47(14) . . . . ?
C13 Ru1 C16 C15 66.55(15) . . . . ?
C12 Ru1 C16 C15 103.61(16) . . . . ?
C14 Ru1 C16 C15 28.64(14) . . . . ?
C11 Ru1 C16 C15 133.0(2) . . . . ?
Cl1 Ru1 C16 C15 17.9(3) . . . . ?
C15 C14 C17 C19 -27.8(4) . . . . ?
C13 C14 C17 C19 150.5(3) . . . . ?
Ru1 C14 C17 C19 63.4(4) . . . . ?
C15 C14 C17 C18 97.9(4) . . . . ?
C13 C14 C17 C18 -83.8(4) . . . . ?
Ru1 C14 C17 C18 -170.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        71.35
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.723
_refine_diff_density_rms         0.077
