# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2003

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

loop_
_publ_author_name
J.Qi
Z.Zhou
C.-w.Yip
'Albert S. C. Chan'

_publ_contact_author_name        'Prof Albert S. C. Chan'
_publ_contact_author_address     
;
Department of Applied Biology and Chemical Technology
The Hong Kong Polytechnic University
Hung Hom, Kowloon
Hong Kong
CHINA
;

_publ_contact_author_email       BCACHAN@POLYU.EDU.HK

_publ_section_title              
;
Highly efficient epoxidation of cyclic alkenes
catalyzed by ruthenium complex
;

data_qjy8
_database_code_CSD               183350

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H17 Cl4 N4 O2 Ru, (C2 H6 O)'
_chemical_formula_sum            'C26 H23 Cl4 N4 O3 Ru'
_chemical_formula_weight         682.35

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   16.706(2)
_cell_length_b                   13.6138(17)
_cell_length_c                   15.7145(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 115.723(3)
_cell_angle_gamma                90.00
_cell_volume                     3219.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    8841
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1372
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8484
_exptl_absorpt_correction_T_max  0.8903
_exptl_absorpt_process_details   'SADABS; SHELXTL NT'

_exptl_special_details           
; 
? 
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD Area Detector'
_diffrn_measurement_method       'phi and omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21254
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_av_sigmaI/netI    0.0879
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         27.60
_reflns_number_total             7385
_reflns_number_gt                3995
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL NT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL NT'
_computing_publication_material  'Bruker SHELXTL NT'

_refine_special_details          
; 
Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
goodness of fit S are based on F^2^, conventional R-factors R are based 
on F, with F set to zero for negative F^2^. The threshold expression of 
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
not relevant to the choice of reflections for refinement.  R-factors based 
on F^2^ 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/[\s^2^(Fo^2^)+(0.0500P)^2^+0.0000P] where P==(Fo^2^+2Fc^2^)/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         7385
_refine_ls_number_parameters     337
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.1058
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1418
_refine_ls_wR_factor_gt          0.1277
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.114
_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 0.23356(2) 0.48583(3) 0.48546(3) 0.04432(15) Uani 1 1 d . . .
Cl1 Cl 0.12381(9) 0.55786(12) 0.35253(10) 0.0743(4) Uani 1 1 d . . .
Cl2 Cl 0.22891(9) 0.61501(11) 0.58371(11) 0.0737(4) Uani 1 1 d . . .
Cl3 Cl 0.35905(12) 0.19670(14) 0.49974(17) 0.1262(8) Uani 1 1 d . . .
Cl4 Cl 0.4100(2) 0.5043(2) 0.8306(2) 0.1868(14) Uani 1 1 d . . .
O1 O 0.3187(3) 0.3423(3) 0.3128(3) 0.0858(13) Uani 1 1 d . . .
O2 O 0.32461(18) 0.4175(2) 0.6053(2) 0.0514(8) Uani 1 1 d . . .
N1 N 0.3299(2) 0.5481(3) 0.4534(3) 0.0466(9) Uani 1 1 d . . .
N2 N 0.2512(2) 0.3775(3) 0.4094(3) 0.0484(10) Uani 1 1 d . . .
N3 N 0.1502(2) 0.4069(3) 0.5252(3) 0.0489(10) Uani 1 1 d . . .
N4 N 0.3405(3) 0.3198(3) 0.7252(3) 0.0649(12) Uani 1 1 d . . .
H4A H 0.3155 0.2833 0.7514 0.078 Uiso 1 1 calc R . .
C1 C 0.3706(3) 0.6334(4) 0.4836(4) 0.0623(14) Uani 1 1 d . . .
H1A H 0.3534 0.6735 0.5206 0.075 Uiso 1 1 calc R . .
C2 C 0.4373(4) 0.6635(5) 0.4614(5) 0.0793(18) Uani 1 1 d . . .
H2A H 0.4657 0.7233 0.4839 0.095 Uiso 1 1 calc R . .
C3 C 0.4622(4) 0.6047(5) 0.4055(4) 0.0754(17) Uani 1 1 d . . .
H3A H 0.5083 0.6238 0.3908 0.090 Uiso 1 1 calc R . .
C4 C 0.4187(4) 0.5187(5) 0.3720(4) 0.0675(15) Uani 1 1 d . . .
H4B H 0.4329 0.4792 0.3322 0.081 Uiso 1 1 calc R . .
C5 C 0.3532(3) 0.4910(4) 0.3980(3) 0.0503(12) Uani 1 1 d . . .
C6 C 0.3063(3) 0.3963(4) 0.3682(4) 0.0586(14) Uani 1 1 d . . .
C7 C 0.2041(3) 0.2870(4) 0.3889(4) 0.0597(14) Uani 1 1 d D . .
C8 C 0.2450(4) 0.1998(4) 0.4266(5) 0.0877(19) Uani 1 1 d D . .
C9 C 0.1984(5) 0.1123(5) 0.4097(6) 0.122(3) Uani 1 1 d D . .
H9A H 0.2276 0.0539 0.4359 0.147 Uiso 1 1 calc R . .
C10 C 0.1093(5) 0.1129(6) 0.3543(6) 0.133(3) Uani 1 1 d D . .
H10A H 0.0773 0.0546 0.3429 0.159 Uiso 1 1 calc R . .
C11 C 0.0663(5) 0.1987(6) 0.3153(6) 0.108(3) Uani 1 1 d D . .
H11A H 0.0054 0.1985 0.2773 0.130 Uiso 1 1 calc R . .
C12 C 0.1134(3) 0.2854(5) 0.3323(4) 0.0748(17) Uani 1 1 d D . .
H12A H 0.0838 0.3435 0.3055 0.090 Uiso 1 1 calc R . .
C13 C 0.0615(3) 0.4048(4) 0.4818(4) 0.0628(15) Uani 1 1 d . . .
H13A H 0.0319 0.4449 0.4295 0.075 Uiso 1 1 calc R . .
C14 C 0.0122(4) 0.3451(5) 0.5123(4) 0.0747(17) Uani 1 1 d . . .
H14A H -0.0495 0.3444 0.4808 0.090 Uiso 1 1 calc R . .
C15 C 0.0559(4) 0.2871(6) 0.5894(5) 0.095(2) Uani 1 1 d . . .
H15A H 0.0242 0.2457 0.6107 0.114 Uiso 1 1 calc R . .
C16 C 0.1470(4) 0.2902(5) 0.6356(4) 0.091(2) Uani 1 1 d . . .
H16A H 0.1773 0.2515 0.6888 0.109 Uiso 1 1 calc R . .
C17 C 0.1927(3) 0.3507(4) 0.6026(3) 0.0524(13) Uani 1 1 d . . .
C18 C 0.2906(3) 0.3640(4) 0.6459(4) 0.0525(13) Uani 1 1 d . . .
C19 C 0.4341(4) 0.3296(5) 0.7696(4) 0.0734(18) Uani 1 1 d D . .
C20 C 0.4714(5) 0.4133(6) 0.8224(5) 0.114(3) Uani 1 1 d D . .
C21 C 0.5654(5) 0.4266(8) 0.8689(6) 0.155(4) Uani 1 1 d D . .
H21A H 0.5934 0.4818 0.9042 0.186 Uiso 1 1 calc R . .
C22 C 0.6093(6) 0.3471(8) 0.8548(6) 0.137(4) Uani 1 1 d D . .
H22A H 0.6709 0.3523 0.8835 0.164 Uiso 1 1 calc R . .
C23 C 0.5769(5) 0.2609(8) 0.8051(6) 0.151(3) Uani 1 1 d D . .
H23A H 0.6149 0.2130 0.8013 0.181 Uiso 1 1 calc R . .
C24 C 0.4844(4) 0.2484(6) 0.7608(5) 0.108(2) Uani 1 1 d D . .
H24A H 0.4577 0.1915 0.7281 0.130 Uiso 1 1 calc R . .
O3 O 0.1467(14) 0.9791(14) 0.6171(15) 0.252(9) Uiso 0.50 1 d PD . .
C25 C 0.1311(13) 0.8772(15) 0.6032(14) 0.153(7) Uiso 0.50 1 d PD . .
C26 C 0.1616(17) 0.8573(19) 0.5272(17) 0.204(10) Uiso 0.50 1 d PD . .
O4 O 0.1511(11) 0.8115(12) 0.3869(12) 0.206(6) Uiso 0.50 1 d PD . .
C27 C 0.2083(13) 0.8216(17) 0.3354(15) 0.191(9) Uiso 0.50 1 d PD . .
C28 C 0.1354(14) 0.8696(16) 0.2522(15) 0.172(8) Uiso 0.50 1 d PD . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ru1 0.0319(2) 0.0562(3) 0.0445(2) -0.00063(19) 0.01627(16) 0.00042(18)
Cl1 0.0529(8) 0.0855(11) 0.0693(9) 0.0206(8) 0.0123(7) 0.0127(7)
Cl2 0.0558(8) 0.0846(11) 0.0884(11) -0.0307(8) 0.0386(8) -0.0081(7)
Cl3 0.0840(13) 0.0789(14) 0.171(2) 0.0058(12) 0.0135(13) 0.0066(10)
Cl4 0.169(3) 0.151(3) 0.165(3) -0.0209(18) 0.002(2) 0.007(2)
O1 0.086(3) 0.090(3) 0.107(3) -0.041(3) 0.066(3) -0.018(2)
O2 0.0339(17) 0.069(2) 0.050(2) 0.0095(17) 0.0174(15) -0.0019(15)
N1 0.042(2) 0.053(3) 0.045(2) 0.0022(19) 0.0199(19) 0.0009(19)
N2 0.038(2) 0.051(3) 0.054(2) -0.0068(19) 0.018(2) -0.0041(18)
N3 0.031(2) 0.068(3) 0.050(2) -0.009(2) 0.0204(19) -0.0045(19)
N4 0.042(3) 0.087(3) 0.067(3) 0.029(3) 0.024(2) -0.001(2)
C1 0.054(3) 0.065(4) 0.072(4) -0.011(3) 0.032(3) -0.013(3)
C2 0.073(4) 0.080(5) 0.093(5) -0.004(4) 0.044(4) -0.024(3)
C3 0.067(4) 0.094(5) 0.079(4) 0.012(4) 0.044(3) -0.018(3)
C4 0.058(3) 0.093(5) 0.062(4) 0.001(3) 0.037(3) -0.005(3)
C5 0.041(3) 0.066(4) 0.046(3) 0.000(2) 0.021(2) 0.001(2)
C6 0.049(3) 0.066(4) 0.062(4) -0.009(3) 0.024(3) 0.001(3)
C7 0.057(4) 0.061(4) 0.067(4) -0.014(3) 0.032(3) -0.008(3)
C8 0.068(4) 0.080(5) 0.108(5) -0.005(4) 0.031(4) -0.010(4)
C9 0.100(6) 0.066(5) 0.180(8) -0.016(5) 0.041(6) -0.020(4)
C10 0.123(8) 0.093(7) 0.186(9) -0.041(6) 0.070(7) -0.054(6)
C11 0.079(5) 0.114(7) 0.132(7) -0.048(6) 0.046(5) -0.028(5)
C12 0.055(4) 0.093(5) 0.076(4) -0.023(3) 0.029(3) -0.017(3)
C13 0.035(3) 0.092(4) 0.062(3) -0.005(3) 0.021(3) -0.002(3)
C14 0.045(3) 0.106(5) 0.078(4) -0.005(4) 0.032(3) -0.011(3)
C15 0.051(4) 0.154(7) 0.087(5) 0.018(5) 0.036(4) -0.026(4)
C16 0.053(4) 0.143(6) 0.075(4) 0.033(4) 0.027(3) -0.012(4)
C17 0.040(3) 0.072(4) 0.049(3) 0.009(3) 0.023(2) -0.004(2)
C18 0.038(3) 0.066(4) 0.052(3) 0.010(3) 0.018(3) 0.001(2)
C19 0.047(3) 0.094(5) 0.069(4) 0.039(4) 0.014(3) -0.003(3)
C20 0.083(5) 0.119(7) 0.108(6) 0.046(5) 0.010(5) -0.004(5)
C21 0.114(8) 0.134(9) 0.140(8) 0.051(7) -0.017(6) -0.040(6)
C22 0.096(6) 0.123 0.157(9) 0.077(7) 0.022(6) -0.003(7)
C23 0.122(8) 0.200 0.155(9) 0.121(7) 0.083(7) 0.091(7)
C24 0.054(4) 0.151 0.113(6) 0.081(5) 0.030(4) 0.027(4)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N2 1.999(4) . ?
Ru1 N3 2.058(4) . ?
Ru1 O2 2.058(3) . ?
Ru1 N1 2.065(4) . ?
Ru1 Cl1 2.3157(13) . ?
Ru1 Cl2 2.3637(14) . ?
Cl3 C8 1.747(6) . ?
Cl4 C20 1.649(9) . ?
O1 C6 1.223(6) . ?
O2 C18 1.257(5) . ?
N1 C1 1.325(6) . ?
N1 C5 1.345(6) . ?
N2 C6 1.359(6) . ?
N2 C7 1.421(6) . ?
N3 C13 1.337(6) . ?
N3 C17 1.349(6) . ?
N4 C18 1.306(6) . ?
N4 C19 1.415(6) . ?
N4 H4A 0.8600 . ?
C1 C2 1.368(7) . ?
C1 H1A 0.9300 . ?
C2 C3 1.380(8) . ?
C2 H2A 0.9300 . ?
C3 C4 1.358(7) . ?
C3 H3A 0.9300 . ?
C4 C5 1.376(7) . ?
C4 H4B 0.9300 . ?
C5 C6 1.475(7) . ?
C7 C8 1.370(6) . ?
C7 C12 1.386(5) . ?
C8 C9 1.385(6) . ?
C9 C10 1.359(6) . ?
C9 H9A 0.9300 . ?
C10 C11 1.369(6) . ?
C10 H10A 0.9300 . ?
C11 C12 1.378(6) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.382(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.362(8) . ?
C14 H14A 0.9300 . ?
C15 C16 1.373(7) . ?
C15 H15A 0.9300 . ?
C16 C17 1.369(7) . ?
C16 H16A 0.9300 . ?
C17 C18 1.484(6) . ?
C19 C20 1.387(6) . ?
C19 C24 1.430(6) . ?
C20 C21 1.426(6) . ?
C21 C22 1.379(7) . ?
C21 H21A 0.9300 . ?
C22 C23 1.383(7) . ?
C22 H22A 0.9300 . ?
C23 C24 1.402(6) . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
O3 C25 1.411(10) . ?
C25 C26 1.513(10) . ?
O4 C27 1.503(10) . ?
C27 C28 1.497(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Ru1 N3 95.22(15) . . ?
N2 Ru1 O2 88.37(14) . . ?
N3 Ru1 O2 79.36(14) . . ?
N2 Ru1 N1 79.85(16) . . ?
N3 Ru1 N1 171.62(15) . . ?
O2 Ru1 N1 93.64(13) . . ?
N2 Ru1 Cl1 92.15(12) . . ?
N3 Ru1 Cl1 96.88(12) . . ?
O2 Ru1 Cl1 176.23(9) . . ?
N1 Ru1 Cl1 90.12(11) . . ?
N2 Ru1 Cl2 174.05(11) . . ?
N3 Ru1 Cl2 88.41(11) . . ?
O2 Ru1 Cl2 87.67(10) . . ?
N1 Ru1 Cl2 95.97(12) . . ?
Cl1 Ru1 Cl2 92.10(6) . . ?
C18 O2 Ru1 114.2(3) . . ?
C1 N1 C5 119.4(4) . . ?
C1 N1 Ru1 127.2(3) . . ?
C5 N1 Ru1 113.3(3) . . ?
C6 N2 C7 118.5(4) . . ?
C6 N2 Ru1 116.9(3) . . ?
C7 N2 Ru1 124.3(3) . . ?
C13 N3 C17 118.7(4) . . ?
C13 N3 Ru1 127.1(4) . . ?
C17 N3 Ru1 114.2(3) . . ?
C18 N4 C19 122.6(4) . . ?
C18 N4 H4A 118.7 . . ?
C19 N4 H4A 118.7 . . ?
N1 C1 C2 121.4(5) . . ?
N1 C1 H1A 119.3 . . ?
C2 C1 H1A 119.3 . . ?
C1 C2 C3 119.5(6) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C3 C4 C5 118.9(5) . . ?
C3 C4 H4B 120.6 . . ?
C5 C4 H4B 120.6 . . ?
N1 C5 C4 121.6(5) . . ?
N1 C5 C6 116.6(4) . . ?
C4 C5 C6 121.8(5) . . ?
O1 C6 N2 125.7(5) . . ?
O1 C6 C5 121.3(5) . . ?
N2 C6 C5 112.9(4) . . ?
C8 C7 C12 117.7(5) . . ?
C8 C7 N2 122.0(5) . . ?
C12 C7 N2 120.2(5) . . ?
C7 C8 C9 122.0(6) . . ?
C7 C8 Cl3 120.1(4) . . ?
C9 C8 Cl3 117.9(5) . . ?
C10 C9 C8 119.1(7) . . ?
C10 C9 H9A 120.4 . . ?
C8 C9 H9A 120.4 . . ?
C9 C10 C11 120.5(7) . . ?
C9 C10 H10A 119.8 . . ?
C11 C10 H10A 119.8 . . ?
C10 C11 C12 120.0(7) . . ?
C10 C11 H11A 120.0 . . ?
C12 C11 H11A 120.0 . . ?
C11 C12 C7 120.7(6) . . ?
C11 C12 H12A 119.6 . . ?
C7 C12 H12A 119.6 . . ?
N3 C13 C14 122.1(5) . . ?
N3 C13 H13A 118.9 . . ?
C14 C13 H13A 118.9 . . ?
C15 C14 C13 118.6(5) . . ?
C15 C14 H14A 120.7 . . ?
C13 C14 H14A 120.7 . . ?
C14 C15 C16 119.8(6) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
C17 C16 C15 119.3(6) . . ?
C17 C16 H16A 120.3 . . ?
C15 C16 H16A 120.3 . . ?
N3 C17 C16 121.4(5) . . ?
N3 C17 C18 112.8(4) . . ?
C16 C17 C18 125.7(5) . . ?
O2 C18 N4 120.6(4) . . ?
O2 C18 C17 119.3(4) . . ?
N4 C18 C17 120.2(4) . . ?
C20 C19 N4 119.1(6) . . ?
C20 C19 C24 124.1(6) . . ?
N4 C19 C24 116.7(6) . . ?
C19 C20 C21 121.4(8) . . ?
C19 C20 Cl4 122.0(6) . . ?
C21 C20 Cl4 116.6(7) . . ?
C22 C21 C20 111.2(9) . . ?
C22 C21 H21A 124.4 . . ?
C20 C21 H21A 124.4 . . ?
C21 C22 C23 130.7(9) . . ?
C21 C22 H22A 114.7 . . ?
C23 C22 H22A 114.7 . . ?
C22 C23 C24 117.4(8) . . ?
C22 C23 H23A 121.3 . . ?
C24 C23 H23A 121.3 . . ?
C23 C24 C19 115.2(7) . . ?
C23 C24 H24A 122.4 . . ?
C19 C24 H24A 122.4 . . ?
O3 C25 C26 101.2(19) . . ?
C28 C27 O4 92.5(16) . . ?

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 O2 C18 -96.6(4) . . . . ?
N3 Ru1 O2 C18 -1.0(4) . . . . ?
N1 Ru1 O2 C18 -176.3(4) . . . . ?
Cl1 Ru1 O2 C18 1.4(18) . . . . ?
Cl2 Ru1 O2 C18 87.8(3) . . . . ?
N2 Ru1 N1 C1 -175.5(4) . . . . ?
N3 Ru1 N1 C1 -121.0(10) . . . . ?
O2 Ru1 N1 C1 -87.8(4) . . . . ?
Cl1 Ru1 N1 C1 92.4(4) . . . . ?
Cl2 Ru1 N1 C1 0.2(4) . . . . ?
N2 Ru1 N1 C5 2.3(3) . . . . ?
N3 Ru1 N1 C5 56.8(11) . . . . ?
O2 Ru1 N1 C5 90.0(3) . . . . ?
Cl1 Ru1 N1 C5 -89.8(3) . . . . ?
Cl2 Ru1 N1 C5 178.0(3) . . . . ?
N3 Ru1 N2 C6 -178.8(3) . . . . ?
O2 Ru1 N2 C6 -99.6(3) . . . . ?
N1 Ru1 N2 C6 -5.6(3) . . . . ?
Cl1 Ru1 N2 C6 84.1(3) . . . . ?
Cl2 Ru1 N2 C6 -51.4(13) . . . . ?
N3 Ru1 N2 C7 7.3(4) . . . . ?
O2 Ru1 N2 C7 86.4(4) . . . . ?
N1 Ru1 N2 C7 -179.6(4) . . . . ?
Cl1 Ru1 N2 C7 -89.8(4) . . . . ?
Cl2 Ru1 N2 C7 134.7(10) . . . . ?
N2 Ru1 N3 C13 -93.2(4) . . . . ?
O2 Ru1 N3 C13 179.5(4) . . . . ?
N1 Ru1 N3 C13 -146.8(10) . . . . ?
Cl1 Ru1 N3 C13 -0.4(4) . . . . ?
Cl2 Ru1 N3 C13 91.5(4) . . . . ?
N2 Ru1 N3 C17 85.4(3) . . . . ?
O2 Ru1 N3 C17 -1.9(3) . . . . ?
N1 Ru1 N3 C17 31.8(12) . . . . ?
Cl1 Ru1 N3 C17 178.2(3) . . . . ?
Cl2 Ru1 N3 C17 -89.9(3) . . . . ?
C5 N1 C1 C2 -1.6(8) . . . . ?
Ru1 N1 C1 C2 176.1(4) . . . . ?
N1 C1 C2 C3 0.8(9) . . . . ?
C1 C2 C3 C4 1.3(9) . . . . ?
C2 C3 C4 C5 -2.5(9) . . . . ?
C1 N1 C5 C4 0.3(7) . . . . ?
Ru1 N1 C5 C4 -177.7(4) . . . . ?
C1 N1 C5 C6 179.0(4) . . . . ?
Ru1 N1 C5 C6 1.0(5) . . . . ?
C3 C4 C5 N1 1.7(8) . . . . ?
C3 C4 C5 C6 -176.9(5) . . . . ?
C7 N2 C6 O1 1.1(8) . . . . ?
Ru1 N2 C6 O1 -173.2(5) . . . . ?
C7 N2 C6 C5 -178.1(4) . . . . ?
Ru1 N2 C6 C5 7.6(5) . . . . ?
N1 C5 C6 O1 175.2(5) . . . . ?
C4 C5 C6 O1 -6.1(8) . . . . ?
N1 C5 C6 N2 -5.6(6) . . . . ?
C4 C5 C6 N2 173.1(5) . . . . ?
C6 N2 C7 C8 74.6(7) . . . . ?
Ru1 N2 C7 C8 -111.5(5) . . . . ?
C6 N2 C7 C12 -108.1(6) . . . . ?
Ru1 N2 C7 C12 65.7(6) . . . . ?
C12 C7 C8 C9 -0.1(10) . . . . ?
N2 C7 C8 C9 177.2(6) . . . . ?
C12 C7 C8 Cl3 -179.2(4) . . . . ?
N2 C7 C8 Cl3 -1.8(8) . . . . ?
C7 C8 C9 C10 -0.2(13) . . . . ?
Cl3 C8 C9 C10 178.9(7) . . . . ?
C8 C9 C10 C11 0.4(14) . . . . ?
C9 C10 C11 C12 -0.2(13) . . . . ?
C10 C11 C12 C7 -0.1(11) . . . . ?
C8 C7 C12 C11 0.3(9) . . . . ?
N2 C7 C12 C11 -177.1(5) . . . . ?
C17 N3 C13 C14 -1.8(8) . . . . ?
Ru1 N3 C13 C14 176.7(4) . . . . ?
N3 C13 C14 C15 0.5(9) . . . . ?
C13 C14 C15 C16 0.8(10) . . . . ?
C14 C15 C16 C17 -0.8(11) . . . . ?
C13 N3 C17 C16 1.8(8) . . . . ?
Ru1 N3 C17 C16 -176.9(5) . . . . ?
C13 N3 C17 C18 -177.2(4) . . . . ?
Ru1 N3 C17 C18 4.1(5) . . . . ?
C15 C16 C17 N3 -0.5(10) . . . . ?
C15 C16 C17 C18 178.3(6) . . . . ?
Ru1 O2 C18 N4 -176.9(4) . . . . ?
Ru1 O2 C18 C17 3.6(6) . . . . ?
C19 N4 C18 O2 0.3(8) . . . . ?
C19 N4 C18 C17 179.9(5) . . . . ?
N3 C17 C18 O2 -5.3(7) . . . . ?
C16 C17 C18 O2 175.8(6) . . . . ?
N3 C17 C18 N4 175.2(5) . . . . ?
C16 C17 C18 N4 -3.7(9) . . . . ?
C18 N4 C19 C20 79.4(8) . . . . ?
C18 N4 C19 C24 -103.9(6) . . . . ?
N4 C19 C20 C21 179.8(6) . . . . ?
C24 C19 C20 C21 3.4(11) . . . . ?
N4 C19 C20 Cl4 -3.1(9) . . . . ?
C24 C19 C20 Cl4 -179.5(5) . . . . ?
C19 C20 C21 C22 -1.1(11) . . . . ?
Cl4 C20 C21 C22 -178.3(6) . . . . ?
C20 C21 C22 C23 -0.4(14) . . . . ?
C21 C22 C23 C24 -0.4(15) . . . . ?
C22 C23 C24 C19 2.4(10) . . . . ?
C20 C19 C24 C23 -4.0(9) . . . . ?
N4 C19 C24 C23 179.6(5) . . . . ?

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
N4 H4A O1 0.86 1.95 2.709(5) 145.9 4_566

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.917
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.095