#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:47:12 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179733 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/29/7002986.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7002986
loop_
_publ_author_name
'Camm, Kenneth D.'
'El-Sokkary, Ahmed'
'Gott, Andrew L.'
'Stockley, Peter G.'
'Belyaeva, Tamara'
'McGowan, Patrick C.'
_publ_section_title
;
 Synthesis, molecular structure and evaluation of new organometallic
 ruthenium anticancer agents
;
_journal_issue                   48
_journal_name_full               'Dalton Transactions'
_journal_page_first              10914
_journal_page_last               10925
_journal_paper_doi               10.1039/b918902e
_journal_year                    2009
_chemical_formula_sum            'C22 H22 Cl N3 O3 Ru'
_chemical_formula_weight         512.95
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.19(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   31.444(6)
_cell_length_b                   8.5608(17)
_cell_length_c                   16.642(3)
_cell_measurement_reflns_used    18394
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     4117.8(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
;
Nonius KappaCCD area-detector diffractometer
;
_diffrn_measurement_method
;
phi and omega scans to fill the asymmetric unit
;
_diffrn_radiation_detector       'CCD plate'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10983
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.94
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_T_max  0.8975
_exptl_absorpt_correction_T_min  0.7633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Using multiple and symmetry-related data
measurements via the program SORTAV. See
R.H. Blessing, Acta Cryst (1995), A51, 33-38.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4001
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0282P)²+8.8714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0922
_reflns_number_gt                3108
_reflns_number_total             4001
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b918902e.txt
_cod_data_source_block           kcrulig4
_cod_original_cell_volume        4118.0(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7002986
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
C3 C 0.1880(2) -0.0794(7) 0.5263(4) 0.087(2) Uani 1 1 d . . .
H3A H 0.1948 -0.1907 0.5385 0.130 Uiso 1 1 calc R . .
H3B H 0.1630 -0.0485 0.5442 0.130 Uiso 1 1 calc R . .
H3C H 0.2158 -0.0180 0.5589 0.130 Uiso 1 1 calc R . .
C1 C 0.2114(3) -0.0900(8) 0.4023(5) 0.137(4) Uani 1 1 d . . .
H1A H 0.2009 -0.0685 0.3396 0.205 Uiso 1 1 calc R . .
H1B H 0.2194 -0.2009 0.4131 0.205 Uiso 1 1 calc R . .
H1C H 0.2387 -0.0263 0.4345 0.205 Uiso 1 1 calc R . .
C2 C 0.17365(17) -0.0510(5) 0.4322(3) 0.0547(12) Uani 1 1 d . . .
H2 H 0.1478 -0.1253 0.4016 0.066 Uiso 1 1 calc R . .
C19 C 0.19393(14) 0.4471(6) 0.7350(3) 0.0491(11) Uani 1 1 d . . .
H19 H 0.2200 0.4262 0.7875 0.059 Uiso 1 1 calc R . .
C20 C 0.18034(14) 0.5985(5) 0.7107(3) 0.0422(10) Uani 1 1 d . . .
C11 C 0.03908(13) -0.0664(4) 0.3647(3) 0.0386(9) Uani 1 1 d . . .
H11 H 0.0373 -0.0445 0.3075 0.046 Uiso 1 1 calc R . .
C17 C 0.13079(12) 0.3565(5) 0.6054(2) 0.0333(9) Uani 1 1 d . . .
C12 C 0.01712(14) -0.1970(5) 0.3783(3) 0.0432(10) Uani 1 1 d . . .
H12 H 0.0008 -0.2646 0.3308 0.052 Uiso 1 1 calc R . .
C10 C 0.09092(16) 0.5655(5) 0.3059(3) 0.0520(12) Uani 1 1 d . . .
H10A H 0.0971 0.6358 0.3557 0.078 Uiso 1 1 calc R . .
H10B H 0.0575 0.5493 0.2759 0.078 Uiso 1 1 calc R . .
H10C H 0.1029 0.6120 0.2652 0.078 Uiso 1 1 calc R . .
C9 C 0.11800(13) 0.1296(4) 0.3180(2) 0.0349(9) Uani 1 1 d . . .
H9 H 0.1070 0.0399 0.2821 0.042 Uiso 1 1 calc R . .
C21 C 0.14261(14) 0.6325(5) 0.6357(2) 0.0407(10) Uani 1 1 d . . .
H21 H 0.1336 0.7378 0.6201 0.049 Uiso 1 1 calc R . .
O2 O 0.19891(12) 0.8602(5) 0.7361(2) 0.0682(10) Uani 1 1 d . . .
O3 O 0.23560(11) 0.6952(5) 0.8388(2) 0.0706(10) Uani 1 1 d . . .
C4 C 0.15483(13) 0.1121(4) 0.4017(2) 0.0339(8) Uani 1 1 d . . .
C7 C 0.11428(13) 0.4115(4) 0.3379(2) 0.0337(8) Uani 1 1 d . . .
C18 C 0.16910(13) 0.3241(5) 0.6820(3) 0.0435(10) Uani 1 1 d . . .
H18 H 0.1783 0.2190 0.6981 0.052 Uiso 1 1 calc R . .
C22 C 0.11786(14) 0.5111(5) 0.5833(2) 0.0378(9) Uani 1 1 d . . .
H22 H 0.0916 0.5337 0.5314 0.045 Uiso 1 1 calc R . .
C8 C 0.09759(13) 0.2736(4) 0.2871(2) 0.0332(8) Uani 1 1 d . . .
H8 H 0.0724 0.2801 0.2318 0.040 Uiso 1 1 calc R . .
C15 C 0.06445(12) 0.0002(4) 0.5112(2) 0.0313(8) Uani 1 1 d . . .
C5 C 0.17059(12) 0.2481(4) 0.4516(2) 0.0345(9) Uani 1 1 d . . .
H5 H 0.1949 0.2407 0.5080 0.041 Uiso 1 1 calc R . .
C13 C 0.01881(15) -0.2296(4) 0.4601(3) 0.0448(11) Uani 1 1 d . . .
H13 H 0.0038 -0.3193 0.4701 0.054 Uiso 1 1 calc R . .
C14 C 0.04280(13) -0.1290(4) 0.5276(3) 0.0392(9) Uani 1 1 d . . .
H14 H 0.0444 -0.1486 0.5849 0.047 Uiso 1 1 calc R . .
C16 C 0.08986(12) 0.1168(4) 0.5803(2) 0.0326(8) Uani 1 1 d . . .
C6 C 0.15106(13) 0.3965(4) 0.4198(2) 0.0352(9) Uani 1 1 d . . .
H6 H 0.1631 0.4869 0.4544 0.042 Uiso 1 1 calc R . .
O1 O 0.09280(10) 0.0993(3) 0.65644(16) 0.0458(7) Uani 1 1 d . . .
N1 N 0.06304(10) 0.0308(3) 0.43050(19) 0.0297(7) Uani 1 1 d . . .
N2 N 0.10588(10) 0.2361(3) 0.54844(18) 0.0300(7) Uani 1 1 d . . .
N3 N 0.20713(12) 0.7286(5) 0.7649(3) 0.0497(10) Uani 1 1 d . . .
Cl1 Cl 0.02345(3) 0.35984(10) 0.38449(6) 0.0330(2) Uani 1 1 d . . .
Ru1 Ru 0.096900(9) 0.23187(3) 0.417030(17) 0.02560(11) Uani 1 1 d . . .
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'
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
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 111.5(5) . . ?
C3 C2 C4 115.0(4) . . ?
C1 C2 C4 110.5(4) . . ?
C3 C2 H2 106.4 . . ?
C1 C2 H2 106.4 . . ?
C4 C2 H2 106.4 . . ?
C20 C19 C18 119.5(4) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C21 C20 C19 121.7(4) . . ?
C21 C20 N3 118.6(4) . . ?
C19 C20 N3 119.8(4) . . ?
N1 C11 C12 121.6(4) . . ?
N1 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C22 C17 C18 119.2(4) . . ?
C22 C17 N2 119.4(3) . . ?
C18 C17 N2 121.4(3) . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9 C4 122.2(3) . . ?
C8 C9 Ru1 72.0(2) . . ?
C4 C9 Ru1 71.1(2) . . ?
C8 C9 H9 118.9 . . ?
C4 C9 H9 118.9 . . ?
Ru1 C9 H9 130.9 . . ?
C20 C21 C22 119.0(4) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C5 C4 C9 116.9(3) . . ?
C5 C4 C2 124.3(4) . . ?
C9 C4 C2 118.7(3) . . ?
C5 C4 Ru1 70.0(2) . . ?
C9 C4 Ru1 70.9(2) . . ?
C2 C4 Ru1 128.5(3) . . ?
C6 C7 C8 118.0(3) . . ?
C6 C7 C10 121.7(4) . . ?
C8 C7 C10 120.2(4) . . ?
C6 C7 Ru1 70.3(2) . . ?
C8 C7 Ru1 70.2(2) . . ?
C10 C7 Ru1 128.0(3) . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C21 C22 C17 121.0(4) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 Ru1 71.0(2) . . ?
C7 C8 Ru1 72.3(2) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
Ru1 C8 H8 129.3 . . ?
N1 C15 C14 121.6(4) . . ?
N1 C15 C16 115.7(3) . . ?
C14 C15 C16 122.7(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 Ru1 72.4(2) . . ?
C6 C5 Ru1 72.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
Ru1 C5 H5 128.3 . . ?
C12 C13 C14 118.5(4) . . ?
C12 C13 H13 120.8 . . ?
C14 C13 H13 120.8 . . ?
C13 C14 C15 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
O1 C16 N2 127.5(4) . . ?
O1 C16 C15 120.4(3) . . ?
N2 C16 C15 112.1(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 Ru1 72.7(2) . . ?
C5 C6 Ru1 69.6(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
Ru1 C6 H6 130.9 . . ?
C11 N1 C15 118.5(3) . . ?
C11 N1 Ru1 124.7(3) . . ?
C15 N1 Ru1 116.7(2) . . ?
C16 N2 C17 119.2(3) . . ?
C16 N2 Ru1 119.0(2) . . ?
C17 N2 Ru1 121.7(2) . . ?
O2 N3 O3 124.5(4) . . ?
O2 N3 C20 118.7(4) . . ?
O3 N3 C20 116.8(4) . . ?
N1 Ru1 N2 76.46(11) . . ?
N1 Ru1 C5 124.38(12) . . ?
N2 Ru1 C5 91.78(13) . . ?
N1 Ru1 C9 94.01(13) . . ?
N2 Ru1 C9 146.96(13) . . ?
C5 Ru1 C9 67.35(14) . . ?
N1 Ru1 C4 96.29(12) . . ?
N2 Ru1 C4 110.69(13) . . ?
C5 Ru1 C4 37.59(13) . . ?
C9 Ru1 C4 38.02(13) . . ?
N1 Ru1 C6 162.39(13) . . ?
N2 Ru1 C6 100.53(13) . . ?
C5 Ru1 C6 38.02(13) . . ?
C9 Ru1 C6 79.05(14) . . ?
C4 Ru1 C6 68.25(14) . . ?
N1 Ru1 C8 116.32(13) . . ?
N2 Ru1 C8 167.16(13) . . ?
C5 Ru1 C8 80.04(14) . . ?
C9 Ru1 C8 36.98(13) . . ?
C4 Ru1 C8 68.36(14) . . ?
C6 Ru1 C8 66.97(14) . . ?
N1 Ru1 C7 152.75(13) . . ?
N2 Ru1 C7 129.98(13) . . ?
C5 Ru1 C7 68.06(14) . . ?
C9 Ru1 C7 67.24(14) . . ?
C4 Ru1 C7 81.11(13) . . ?
C6 Ru1 C7 36.98(14) . . ?
C8 Ru1 C7 37.56(13) . . ?
N1 Ru1 Cl1 85.11(8) . . ?
N2 Ru1 Cl1 87.14(9) . . ?
C5 Ru1 Cl1 149.36(10) . . ?
C9 Ru1 Cl1 124.00(10) . . ?
C4 Ru1 Cl1 161.97(10) . . ?
C6 Ru1 Cl1 112.23(10) . . ?
C8 Ru1 Cl1 94.85(10) . . ?
C7 Ru1 Cl1 89.42(10) . . ?
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
C3 C2 1.470(6) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C1 C2 1.495(7) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.523(5) . ?
C2 H2 1.0000 . ?
C19 C20 1.375(6) . ?
C19 C18 1.398(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.372(6) . ?
C20 N3 1.472(5) . ?
C11 N1 1.345(5) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9500 . ?
C17 C22 1.391(5) . ?
C17 C18 1.394(5) . ?
C17 N2 1.411(5) . ?
C12 C13 1.370(6) . ?
C12 H12 0.9500 . ?
C10 C7 1.501(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9 C8 1.392(5) . ?
C9 C4 1.426(5) . ?
C9 Ru1 2.187(3) . ?
C9 H9 0.9500 . ?
C21 C22 1.383(5) . ?
C21 H21 0.9500 . ?
O2 N3 1.211(5) . ?
O3 N3 1.236(5) . ?
C4 C5 1.402(5) . ?
C4 Ru1 2.191(4) . ?
C7 C6 1.404(5) . ?
C7 C8 1.426(5) . ?
C7 Ru1 2.229(3) . ?
C18 H18 0.9500 . ?
C22 H22 0.9500 . ?
C8 Ru1 2.200(3) . ?
C8 H8 0.9500 . ?
C15 N1 1.353(4) . ?
C15 C14 1.381(5) . ?
C15 C16 1.494(5) . ?
C5 C6 1.420(5) . ?
C5 Ru1 2.161(4) . ?
C5 H5 0.9500 . ?
C13 C14 1.380(6) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 O1 1.243(4) . ?
C16 N2 1.337(5) . ?
C6 Ru1 2.197(4) . ?
C6 H6 0.9500 . ?
N1 Ru1 2.082(3) . ?
N2 Ru1 2.092(3) . ?
Cl1 Ru1 2.4171(10) . ?
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
C18 C19 C20 C21 0.5(6) . . . . ?
C18 C19 C20 N3 -178.2(4) . . . . ?
N1 C11 C12 C13 0.9(6) . . . . ?
C19 C20 C21 C22 -0.3(6) . . . . ?
N3 C20 C21 C22 178.5(3) . . . . ?
C8 C9 C4 C5 -1.4(5) . . . . ?
Ru1 C9 C4 C5 -54.4(3) . . . . ?
C8 C9 C4 C2 177.2(4) . . . . ?
Ru1 C9 C4 C2 124.1(3) . . . . ?
C8 C9 C4 Ru1 53.1(3) . . . . ?
C3 C2 C4 C5 34.0(6) . . . . ?
C1 C2 C4 C5 -93.3(6) . . . . ?
C3 C2 C4 C9 -144.4(4) . . . . ?
C1 C2 C4 C9 88.3(6) . . . . ?
C3 C2 C4 Ru1 -56.8(6) . . . . ?
C1 C2 C4 Ru1 175.9(4) . . . . ?
C22 C17 C18 C19 -0.3(6) . . . . ?
N2 C17 C18 C19 177.5(4) . . . . ?
C20 C19 C18 C17 -0.3(6) . . . . ?
C20 C21 C22 C17 -0.3(6) . . . . ?
C18 C17 C22 C21 0.5(6) . . . . ?
N2 C17 C22 C21 -177.3(3) . . . . ?
C4 C9 C8 C7 2.2(5) . . . . ?
Ru1 C9 C8 C7 54.9(3) . . . . ?
C4 C9 C8 Ru1 -52.7(3) . . . . ?
C6 C7 C8 C9 -1.1(5) . . . . ?
C10 C7 C8 C9 -177.5(3) . . . . ?
Ru1 C7 C8 C9 -54.3(3) . . . . ?
C6 C7 C8 Ru1 53.2(3) . . . . ?
C10 C7 C8 Ru1 -123.2(3) . . . . ?
C9 C4 C5 C6 -0.6(5) . . . . ?
C2 C4 C5 C6 -179.1(4) . . . . ?
Ru1 C4 C5 C6 -55.5(3) . . . . ?
C9 C4 C5 Ru1 54.8(3) . . . . ?
C2 C4 C5 Ru1 -123.6(4) . . . . ?
C11 C12 C13 C14 0.0(6) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
N1 C15 C14 C13 -0.4(6) . . . . ?
C16 C15 C14 C13 178.1(3) . . . . ?
N1 C15 C16 O1 179.6(3) . . . . ?
C14 C15 C16 O1 0.9(5) . . . . ?
N1 C15 C16 N2 1.9(4) . . . . ?
C14 C15 C16 N2 -176.7(3) . . . . ?
C8 C7 C6 C5 -0.9(5) . . . . ?
C10 C7 C6 C5 175.5(3) . . . . ?
Ru1 C7 C6 C5 52.3(3) . . . . ?
C8 C7 C6 Ru1 -53.2(3) . . . . ?
C10 C7 C6 Ru1 123.2(3) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
Ru1 C5 C6 C7 -53.7(3) . . . . ?
C4 C5 C6 Ru1 55.5(3) . . . . ?
C12 C11 N1 C15 -1.5(5) . . . . ?
C12 C11 N1 Ru1 -179.4(3) . . . . ?
C14 C15 N1 C11 1.3(5) . . . . ?
C16 C15 N1 C11 -177.4(3) . . . . ?
C14 C15 N1 Ru1 179.3(3) . . . . ?
C16 C15 N1 Ru1 0.7(4) . . . . ?
O1 C16 N2 C17 2.6(6) . . . . ?
C15 C16 N2 C17 -179.9(3) . . . . ?
O1 C16 N2 Ru1 178.8(3) . . . . ?
C15 C16 N2 Ru1 -3.7(4) . . . . ?
C22 C17 N2 C16 -128.7(4) . . . . ?
C18 C17 N2 C16 53.5(5) . . . . ?
C22 C17 N2 Ru1 55.2(4) . . . . ?
C18 C17 N2 Ru1 -122.6(3) . . . . ?
C21 C20 N3 O2 -9.7(6) . . . . ?
C19 C20 N3 O2 169.2(4) . . . . ?
C21 C20 N3 O3 167.7(4) . . . . ?
C19 C20 N3 O3 -13.4(5) . . . . ?
C11 N1 Ru1 N2 175.9(3) . . . . ?
C15 N1 Ru1 N2 -2.0(2) . . . . ?
C11 N1 Ru1 C5 -101.3(3) . . . . ?
C15 N1 Ru1 C5 80.8(3) . . . . ?
C11 N1 Ru1 C9 -36.1(3) . . . . ?
C15 N1 Ru1 C9 146.0(3) . . . . ?
C11 N1 Ru1 C4 -74.2(3) . . . . ?
C15 N1 Ru1 C4 107.8(3) . . . . ?
C11 N1 Ru1 C6 -102.0(5) . . . . ?
C15 N1 Ru1 C6 80.1(5) . . . . ?
C11 N1 Ru1 C8 -5.3(3) . . . . ?
C15 N1 Ru1 C8 176.8(2) . . . . ?
C11 N1 Ru1 C7 8.6(5) . . . . ?
C15 N1 Ru1 C7 -169.4(3) . . . . ?
C11 N1 Ru1 Cl1 87.7(3) . . . . ?
C15 N1 Ru1 Cl1 -90.2(2) . . . . ?
C16 N2 Ru1 N1 3.2(3) . . . . ?
C17 N2 Ru1 N1 179.3(3) . . . . ?
C16 N2 Ru1 C5 -121.8(3) . . . . ?
C17 N2 Ru1 C5 54.3(3) . . . . ?
C16 N2 Ru1 C9 -73.0(4) . . . . ?
C17 N2 Ru1 C9 103.1(3) . . . . ?
C16 N2 Ru1 C4 -88.4(3) . . . . ?
C17 N2 Ru1 C4 87.6(3) . . . . ?
C16 N2 Ru1 C6 -159.0(3) . . . . ?
C17 N2 Ru1 C6 17.1(3) . . . . ?
C16 N2 Ru1 C8 -171.8(5) . . . . ?
C17 N2 Ru1 C8 4.3(7) . . . . ?
C16 N2 Ru1 C7 175.7(2) . . . . ?
C17 N2 Ru1 C7 -8.2(3) . . . . ?
C16 N2 Ru1 Cl1 88.9(3) . . . . ?
C17 N2 Ru1 Cl1 -95.0(3) . . . . ?
C4 C5 Ru1 N1 47.8(3) . . . . ?
C6 C5 Ru1 N1 -179.67(19) . . . . ?
C4 C5 Ru1 N2 122.6(2) . . . . ?
C6 C5 Ru1 N2 -104.9(2) . . . . ?
C4 C5 Ru1 C9 -31.0(2) . . . . ?
C6 C5 Ru1 C9 101.5(2) . . . . ?
C6 C5 Ru1 C4 132.5(3) . . . . ?
C4 C5 Ru1 C6 -132.5(3) . . . . ?
C4 C5 Ru1 C8 -67.3(2) . . . . ?
C6 C5 Ru1 C8 65.2(2) . . . . ?
C4 C5 Ru1 C7 -104.5(2) . . . . ?
C6 C5 Ru1 C7 28.0(2) . . . . ?
C4 C5 Ru1 Cl1 -149.96(18) . . . . ?
C6 C5 Ru1 Cl1 -17.5(3) . . . . ?
C8 C9 Ru1 N1 130.2(2) . . . . ?
C4 C9 Ru1 N1 -95.1(2) . . . . ?
C8 C9 Ru1 N2 -158.6(2) . . . . ?
C4 C9 Ru1 N2 -23.9(3) . . . . ?
C8 C9 Ru1 C5 -104.0(2) . . . . ?
C4 C9 Ru1 C5 30.7(2) . . . . ?
C8 C9 Ru1 C4 -134.7(3) . . . . ?
C8 C9 Ru1 C6 -66.1(2) . . . . ?
C4 C9 Ru1 C6 68.6(2) . . . . ?
C4 C9 Ru1 C8 134.7(3) . . . . ?
C8 C9 Ru1 C7 -29.3(2) . . . . ?
C4 C9 Ru1 C7 105.3(2) . . . . ?
C8 C9 Ru1 Cl1 43.4(2) . . . . ?
C4 C9 Ru1 Cl1 178.11(17) . . . . ?
C5 C4 Ru1 N1 -142.0(2) . . . . ?
C9 C4 Ru1 N1 88.5(2) . . . . ?
C2 C4 Ru1 N1 -23.5(4) . . . . ?
C5 C4 Ru1 N2 -64.1(2) . . . . ?
C9 C4 Ru1 N2 166.3(2) . . . . ?
C2 C4 Ru1 N2 54.4(4) . . . . ?
C9 C4 Ru1 C5 -129.5(3) . . . . ?
C2 C4 Ru1 C5 118.5(5) . . . . ?
C5 C4 Ru1 C9 129.5(3) . . . . ?
C2 C4 Ru1 C9 -112.0(4) . . . . ?
C5 C4 Ru1 C6 29.3(2) . . . . ?
C9 C4 Ru1 C6 -100.3(2) . . . . ?
C2 C4 Ru1 C6 147.8(4) . . . . ?
C5 C4 Ru1 C8 102.1(2) . . . . ?
C9 C4 Ru1 C8 -27.4(2) . . . . ?
C2 C4 Ru1 C8 -139.4(4) . . . . ?
C5 C4 Ru1 C7 65.4(2) . . . . ?
C9 C4 Ru1 C7 -64.2(2) . . . . ?
C2 C4 Ru1 C7 -176.1(4) . . . . ?
C5 C4 Ru1 Cl1 124.5(3) . . . . ?
C9 C4 Ru1 Cl1 -5.1(5) . . . . ?
C2 C4 Ru1 Cl1 -117.0(4) . . . . ?
C7 C6 Ru1 N1 134.5(4) . . . . ?
C5 C6 Ru1 N1 0.9(5) . . . . ?
C7 C6 Ru1 N2 -147.1(2) . . . . ?
C5 C6 Ru1 N2 79.3(2) . . . . ?
C7 C6 Ru1 C5 133.6(3) . . . . ?
C7 C6 Ru1 C9 66.5(2) . . . . ?
C5 C6 Ru1 C9 -67.1(2) . . . . ?
C7 C6 Ru1 C4 104.7(2) . . . . ?
C5 C6 Ru1 C4 -29.0(2) . . . . ?
C7 C6 Ru1 C8 29.8(2) . . . . ?
C5 C6 Ru1 C8 -103.8(2) . . . . ?
C5 C6 Ru1 C7 -133.6(3) . . . . ?
C7 C6 Ru1 Cl1 -55.9(2) . . . . ?
C5 C6 Ru1 Cl1 170.48(18) . . . . ?
C9 C8 Ru1 N1 -58.2(2) . . . . ?
C7 C8 Ru1 N1 169.65(19) . . . . ?
C9 C8 Ru1 N2 116.4(6) . . . . ?
C7 C8 Ru1 N2 -15.8(7) . . . . ?
C9 C8 Ru1 C5 65.4(2) . . . . ?
C7 C8 Ru1 C5 -66.8(2) . . . . ?
C7 C8 Ru1 C9 -132.2(3) . . . . ?
C9 C8 Ru1 C4 28.1(2) . . . . ?
C7 C8 Ru1 C4 -104.1(2) . . . . ?
C9 C8 Ru1 C6 102.8(2) . . . . ?
C7 C8 Ru1 C6 -29.4(2) . . . . ?
C9 C8 Ru1 C7 132.2(3) . . . . ?
C9 C8 Ru1 Cl1 -145.1(2) . . . . ?
C7 C8 Ru1 Cl1 82.7(2) . . . . ?
C6 C7 Ru1 N1 -151.9(3) . . . . ?
C8 C7 Ru1 N1 -20.6(4) . . . . ?
C10 C7 Ru1 N1 92.7(4) . . . . ?
C6 C7 Ru1 N2 44.2(3) . . . . ?
C8 C7 Ru1 N2 175.48(19) . . . . ?
C10 C7 Ru1 N2 -71.2(4) . . . . ?
C6 C7 Ru1 C5 -28.7(2) . . . . ?
C8 C7 Ru1 C5 102.6(2) . . . . ?
C10 C7 Ru1 C5 -144.1(4) . . . . ?
C6 C7 Ru1 C9 -102.4(2) . . . . ?
C8 C7 Ru1 C9 28.9(2) . . . . ?
C10 C7 Ru1 C9 142.2(4) . . . . ?
C6 C7 Ru1 C4 -65.4(2) . . . . ?
C8 C7 Ru1 C4 65.9(2) . . . . ?
C10 C7 Ru1 C4 179.2(4) . . . . ?
C8 C7 Ru1 C6 131.3(3) . . . . ?
C10 C7 Ru1 C6 -115.4(5) . . . . ?
C6 C7 Ru1 C8 -131.3(3) . . . . ?
C10 C7 Ru1 C8 113.3(5) . . . . ?
C6 C7 Ru1 Cl1 130.0(2) . . . . ?
C8 C7 Ru1 Cl1 -98.7(2) . . . . ?
C10 C7 Ru1 Cl1 14.6(4) . . . . ?
