# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1477955'
_audit_update_record             
;
2016-05-04 deposited with the CCDC.
2016-06-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          '350 deg decomp'
_chemical_formula_moiety         'C28 H24 N4 O6 Ru, (H2 O)'
_chemical_formula_sum            'C28 H26 N4 O7 Ru'
_chemical_formula_weight         631.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0041 0.0020 '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 0.0078 0.0041 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0135 0.0075 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -0.9769 1.0012 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'

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

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

_cell_length_a                   10.9419(6)
_cell_length_b                   24.4770(12)
_cell_length_c                   11.0478(9)
_cell_angle_alpha                90
_cell_angle_beta                 118.7234(16)
_cell_angle_gamma                90
_cell_volume                     2594.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    15847
_cell_measurement_theta_min      1.833
_cell_measurement_theta_max      27.997

_exptl_crystal_description       pletelet
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.842
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (T.Higashi, 2001)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.78305
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'Synchrotron radiation SPring-8 BL40XU'
_diffrn_radiation_monochromator  'Si(111) Channel Cut'
_diffrn_measurement_device_type  'Rigaku Saturn 724'
_diffrn_measurement_method       'Oscillation Photograph'
_diffrn_detector_area_resol_mean 29
_diffrn_reflns_number            15847
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_full        27.997
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_reflns_number_total             4597
_reflns_number_gt                3631
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'Rapid Auto(Rigaku)'
_computing_cell_refinement       'Rapid Auto(Rigaku)'
_computing_data_reduction        'Rapid Auto(Rigaku)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²+6.5700P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4597
_refine_ls_number_parameters     396
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          '< 0.001'
_refine_ls_shift/su_mean         '< 0.001'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.75502(3) 0.13232(2) 0.05452(4) 0.02600(12) Uani 1 1 d . . . . .
N1 N 0.7239(4) 0.20979(13) 0.1054(4) 0.0316(8) Uani 1 1 d . . . . .
N2 N 0.8049(3) 0.17528(13) -0.0634(4) 0.0298(8) Uani 1 1 d . . . . .
N3 N 0.8019(3) 0.07085(13) -0.0416(4) 0.0273(8) Uani 1 1 d . . . . .
N4 N 0.7135(3) 0.08685(13) 0.1771(4) 0.0269(8) Uani 1 1 d . . . . .
O1 O 0.9541(3) 0.12358(10) 0.2270(3) 0.0296(7) Uani 1 1 d . . . . .
O2 O 1.0650(3) 0.08129(13) 0.4304(3) 0.0365(7) Uani 1 1 d . . . . .
O3 O 0.5365(3) 0.12167(11) -0.0653(3) 0.0334(7) Uani 1 1 d . . . . .
O4 O 0.3551(3) 0.08322(12) -0.0560(3) 0.0368(7) Uani 1 1 d . . . . .
C1 C 0.6724(5) 0.22417(18) 0.1914(5) 0.0378(11) Uani 1 1 d . . . . .
H1 H 0.6520 0.1961 0.2385 0.045 Uiso 1 1 calc R U . . .
C2 C 0.6489(5) 0.27735(18) 0.2129(6) 0.0504(14) Uani 1 1 d . . . . .
H2 H 0.6121 0.2858 0.2730 0.060 Uiso 1 1 calc R U . . .
C3 C 0.6793(5) 0.31815(18) 0.1465(6) 0.0493(14) Uani 1 1 d . . . . .
H3 H 0.6643 0.3553 0.1610 0.059 Uiso 1 1 calc R U . . .
C4 C 0.7316(5) 0.30521(18) 0.0588(6) 0.0428(12) Uani 1 1 d . . . . .
H4 H 0.7532 0.3333 0.0128 0.051 Uiso 1 1 calc R U . . .
C5 C 0.7528(4) 0.25038(16) 0.0379(5) 0.0338(10) Uani 1 1 d . . . . .
C6 C 0.8026(4) 0.23129(17) -0.0565(5) 0.0344(10) Uani 1 1 d . . . . .
C7 C 0.8445(5) 0.2622(2) -0.1348(5) 0.0443(12) Uani 1 1 d . . . . .
H7 H 0.8419 0.3010 -0.1324 0.053 Uiso 1 1 calc R U . . .
C8 C 0.8896(6) 0.2362(2) -0.2159(6) 0.0530(14) Uani 1 1 d . . . . .
H8 H 0.9195 0.2574 -0.2690 0.064 Uiso 1 1 calc R U . . .
C9 C 0.8927(5) 0.1786(2) -0.2223(5) 0.0442(12) Uani 1 1 d . . . . .
H9 H 0.9237 0.1608 -0.2791 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8491(4) 0.14898(18) -0.1436(5) 0.0340(10) Uani 1 1 d . . . . .
C11 C 0.8447(4) 0.08890(17) -0.1329(5) 0.0309(10) Uani 1 1 d . . . . .
C12 C 0.8798(4) 0.0524(2) -0.2073(5) 0.0396(11) Uani 1 1 d . . . . .
H12 H 0.9114 0.0652 -0.2687 0.048 Uiso 1 1 calc R U . . .
C13 C 0.8678(5) -0.0037(2) -0.1903(6) 0.0469(13) Uani 1 1 d . . . . .
H13 H 0.8895 -0.0294 -0.2417 0.056 Uiso 1 1 calc R U . . .
C14 C 0.8247(5) -0.02138(19) -0.0994(5) 0.0410(12) Uani 1 1 d . . . . .
H14 H 0.8164 -0.0593 -0.0867 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7937(4) 0.01665(16) -0.0265(5) 0.0325(10) Uani 1 1 d . . . . .
H15 H 0.7651 0.0041 0.0374 0.039 Uiso 1 1 calc R U . . .
C16 C 0.9583(5) 0.09278(17) 0.3250(5) 0.0293(10) Uani 1 1 d . . . . .
C17 C 0.8180(4) 0.07016(16) 0.2980(5) 0.0289(9) Uani 1 1 d . . . . .
C18 C 0.7955(5) 0.03360(19) 0.3811(5) 0.0367(11) Uani 1 1 d . . . . .
H18 H 0.8708 0.0218 0.4663 0.044 Uiso 1 1 calc R U . . .
C19 C 0.6601(5) 0.0143(2) 0.3377(5) 0.0436(12) Uani 1 1 d . . . . .
C20 C 0.5536(5) 0.03386(19) 0.2138(5) 0.0373(11) Uani 1 1 d . . . . .
H20 H 0.4604 0.0224 0.1834 0.045 Uiso 1 1 calc R U . . .
C21 C 0.5821(4) 0.06980(16) 0.1342(5) 0.0292(9) Uani 1 1 d . . . . .
C22 C 0.4811(4) 0.09267(16) -0.0056(5) 0.0314(10) Uani 1 1 d . . . . .
O5A O 0.4875(11) -0.2433(2) 0.4449(8) 0.066(2) Uani 0.730(10) 1 d . . P A 2
O6A O 0.4423(8) -0.1927(3) 0.5818(9) 0.0467(17) Uani 0.730(10) 1 d . . P A 2
C23A C 0.6344(7) -0.0357(3) 0.4213(6) 0.0290(15) Uani 0.730(10) 1 d . . P A 2
H23A H 0.6823 -0.0687 0.4131 0.035 Uiso 0.730(10) 1 calc R U P A 2
H23B H 0.6788 -0.0259 0.5203 0.035 Uiso 0.730(10) 1 calc R U P A 2
C24A C 0.4921(7) -0.0494(3) 0.3763(7) 0.0381(18) Uani 0.730(10) 1 d . . P A 2
H24A H 0.4478 -0.0617 0.2791 0.046 Uiso 0.730(10) 1 calc R U P A 2
H24B H 0.4418 -0.0165 0.3808 0.046 Uiso 0.730(10) 1 calc R U P A 2
C25A C 0.4797(8) -0.0940(2) 0.4648(8) 0.0396(18) Uani 0.730(10) 1 d . . P A 2
H25A H 0.3818 -0.0962 0.4462 0.048 Uiso 0.730(10) 1 calc R U P A 2
H25B H 0.5383 -0.0844 0.5634 0.048 Uiso 0.730(10) 1 calc R U P A 2
C26A C 0.5254(7) -0.1513(2) 0.4374(7) 0.0308(16) Uani 0.730(10) 1 d . . P A 2
H26A H 0.4849 -0.1565 0.3366 0.037 Uiso 0.730(10) 1 calc R U P A 2
H26B H 0.6281 -0.1517 0.4779 0.037 Uiso 0.730(10) 1 calc R U P A 2
C27A C 0.4822(9) -0.1979(3) 0.4957(9) 0.0392(19) Uani 0.730(10) 1 d . . P A 2
C28A C 0.4434(16) -0.2888(4) 0.4932(12) 0.088(4) Uani 0.730(10) 1 d . . P A 2
H28A H 0.5142 -0.2974 0.5880 0.132 Uiso 0.730(10) 1 calc R U P A 2
H28B H 0.4302 -0.3203 0.4336 0.132 Uiso 0.730(10) 1 calc R U P A 2
H28C H 0.3551 -0.2801 0.4916 0.132 Uiso 0.730(10) 1 calc R U P A 2
O5B O 0.563(2) -0.2376(9) 0.496(2) 0.072(7) Uiso 0.270(10) 1 d . . P A 3
O6B O 0.463(5) -0.1816(17) 0.619(5) 0.139(18) Uiso 0.270(10) 1 d . . P A 3
C23B C 0.614(2) -0.0104(9) 0.420(2) 0.035(5) Uiso 0.270(10) 1 d . . P A 3
H23C H 0.5327 0.0094 0.4159 0.041 Uiso 0.270(10) 1 calc R U P A 3
H23D H 0.6886 -0.0118 0.5176 0.041 Uiso 0.270(10) 1 calc R U P A 3
C24B C 0.575(2) -0.0642(9) 0.364(2) 0.049(6) Uiso 0.270(10) 1 d . . P A 3
H24C H 0.6588 -0.0794 0.3639 0.059 Uiso 0.270(10) 1 calc R U P A 3
H24D H 0.5054 -0.0587 0.2655 0.059 Uiso 0.270(10) 1 calc R U P A 3
C25B C 0.515(4) -0.1123(16) 0.417(4) 0.098(10) Uiso 0.270(10) 1 d . . P A 3
H25C H 0.4335 -0.0976 0.4227 0.118 Uiso 0.270(10) 1 calc R U P A 3
H25D H 0.4788 -0.1408 0.3442 0.118 Uiso 0.270(10) 1 calc R U P A 3
C26B C 0.589(4) -0.1349(13) 0.526(4) 0.094(10) Uiso 0.270(10) 1 d . . P A 3
H26C H 0.6109 -0.1092 0.6026 0.113 Uiso 0.270(10) 1 calc R U P A 3
H26D H 0.6783 -0.1452 0.5287 0.113 Uiso 0.270(10) 1 calc R U P A 3
C27B C 0.519(3) -0.1870(10) 0.545(3) 0.040(7) Uiso 0.270(10) 1 d . . P A 3
C28B C 0.520(3) -0.2910(12) 0.531(3) 0.053(7) Uiso 0.270(10) 1 d . . P A 3
H28D H 0.5355 -0.2896 0.6264 0.080 Uiso 0.270(10) 1 calc R U P A 3
H28E H 0.5756 -0.3206 0.5228 0.080 Uiso 0.270(10) 1 calc R U P A 3
H28F H 0.4210 -0.2976 0.4681 0.080 Uiso 0.270(10) 1 calc R U P A 3
O7A O 1.0975(6) 0.0881(5) 0.7000(6) 0.037(2) Uiso 0.66(3) 1 d . . P B 3
H7A H 1.0856 0.0855 0.6046 0.056 Uiso 0.66(3) 1 d R U P B 3
H7B H 1.1889 0.0861 0.7867 0.056 Uiso 0.66(3) 1 d R U P B 3
O7B O 1.1083(12) 0.1103(10) 0.6986(11) 0.041(5) Uiso 0.34(3) 1 d . . P B 4
H7C H 1.0928 0.1003 0.6045 0.061 Uiso 0.34(3) 1 d R U P B 4
H7D H 1.1952 0.1009 0.7854 0.061 Uiso 0.34(3) 1 d R U P B 4


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N2 1.945(3) . ?
Ru1 N4 1.967(3) . ?
Ru1 N3 2.044(3) . ?
Ru1 N1 2.052(3) . ?
Ru1 O1 2.105(3) . ?
Ru1 O3 2.120(3) . ?
N1 C1 1.364(5) . ?
N1 C5 1.368(5) . ?
N2 C10 1.359(6) . ?
N2 C6 1.374(5) . ?
N3 C15 1.346(5) . ?
N3 C11 1.373(5) . ?
N4 C17 1.338(6) . ?
N4 C21 1.345(5) . ?
O1 C16 1.301(5) . ?
O2 C16 1.221(5) . ?
O3 C22 1.299(5) . ?
O4 C22 1.236(5) . ?
C1 C2 1.369(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.371(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.400(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.466(6) . ?
C6 C7 1.383(6) . ?
C7 C8 1.370(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.414(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.478(6) . ?
C11 C12 1.388(6) . ?
C12 C13 1.402(7) . ?
C12 H12 0.9500 . ?
C13 C14 1.369(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.376(6) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.520(5) . ?
C17 C18 1.387(6) . ?
C18 C19 1.403(6) . ?
C18 H18 0.9500 . ?
C19 C23B 1.38(2) . ?
C19 C20 1.389(7) . ?
C19 C23A 1.637(8) . ?
C20 C21 1.381(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.510(6) . ?
O5A C27A 1.258(10) . ?
O5A C28A 1.417(12) . ?
O6A C27A 1.230(10) . ?
C23A C24A 1.428(9) . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C24A C25A 1.515(8) . ?
C24A H24A 0.9900 . ?
C24A H24B 0.9900 . ?
C25A C26A 1.565(9) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A C27A 1.495(10) . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C28A H28A 0.9800 . ?
C28A H28B 0.9800 . ?
C28A H28C 0.9800 . ?
O5B C28B 1.50(4) . ?
O5B C27B 1.52(3) . ?
O6B C27B 1.24(5) . ?
C23B C24B 1.43(3) . ?
C23B H23C 0.9900 . ?
C23B H23D 0.9900 . ?
C24B C25B 1.59(4) . ?
C24B H24C 0.9900 . ?
C24B H24D 0.9900 . ?
C25B C26B 1.22(4) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C26B C27B 1.56(4) . ?
C26B H26C 0.9900 . ?
C26B H26D 0.9900 . ?
C28B H28D 0.9800 . ?
C28B H28E 0.9800 . ?
C28B H28F 0.9800 . ?
O7A H7A 0.9999 . ?
O7A H7B 1.0000 . ?
O7B H7C 1.0000 . ?
O7B H7D 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
N2 Ru1 N4 177.11(13) . . ?
N2 Ru1 N3 80.15(14) . . ?
N4 Ru1 N3 98.04(13) . . ?
N2 Ru1 N1 79.67(14) . . ?
N4 Ru1 N1 102.16(13) . . ?
N3 Ru1 N1 159.80(14) . . ?
N2 Ru1 O1 99.20(12) . . ?
N4 Ru1 O1 78.48(12) . . ?
N3 Ru1 O1 89.24(12) . . ?
N1 Ru1 O1 94.68(12) . . ?
N2 Ru1 O3 104.10(13) . . ?
N4 Ru1 O3 78.22(13) . . ?
N3 Ru1 O3 94.28(12) . . ?
N1 Ru1 O3 89.92(12) . . ?
O1 Ru1 O3 156.69(11) . . ?
C1 N1 C5 118.3(4) . . ?
C1 N1 Ru1 127.4(3) . . ?
C5 N1 Ru1 114.2(3) . . ?
C10 N2 C6 122.0(4) . . ?
C10 N2 Ru1 118.9(3) . . ?
C6 N2 Ru1 119.0(3) . . ?
C15 N3 C11 118.4(3) . . ?
C15 N3 Ru1 127.8(3) . . ?
C11 N3 Ru1 113.8(3) . . ?
C17 N4 C21 120.9(4) . . ?
C17 N4 Ru1 119.4(3) . . ?
C21 N4 Ru1 119.6(3) . . ?
C16 O1 Ru1 114.8(2) . . ?
C22 O3 Ru1 114.3(3) . . ?
N1 C1 C2 122.7(4) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C1 C2 C3 119.1(5) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N1 C5 C4 120.4(4) . . ?
N1 C5 C6 114.8(3) . . ?
C4 C5 C6 124.8(4) . . ?
N2 C6 C7 119.5(4) . . ?
N2 C6 C5 112.3(4) . . ?
C7 C6 C5 128.2(4) . . ?
C8 C7 C6 119.1(4) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 117.9(4) . . ?
C10 C9 H9 121.0 . . ?
C8 C9 H9 121.0 . . ?
N2 C10 C9 120.1(4) . . ?
N2 C10 C11 112.5(4) . . ?
C9 C10 C11 127.4(4) . . ?
N3 C11 C12 121.2(4) . . ?
N3 C11 C10 114.5(4) . . ?
C12 C11 C10 124.3(4) . . ?
C11 C12 C13 118.7(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 119.0(4) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 123.0(4) . . ?
N3 C15 H15 118.5 . . ?
C14 C15 H15 118.5 . . ?
O2 C16 O1 124.2(4) . . ?
O2 C16 C17 121.0(4) . . ?
O1 C16 C17 114.8(4) . . ?
N4 C17 C18 121.3(4) . . ?
N4 C17 C16 112.5(4) . . ?
C18 C17 C16 126.1(4) . . ?
C17 C18 C19 119.1(4) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C23B C19 C20 113.8(10) . . ?
C23B C19 C18 125.9(10) . . ?
C20 C19 C18 117.9(4) . . ?
C20 C19 C23A 121.6(4) . . ?
C18 C19 C23A 119.9(5) . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
N4 C21 C20 120.2(4) . . ?
N4 C21 C22 112.2(4) . . ?
C20 C21 C22 127.5(4) . . ?
O4 C22 O3 124.4(4) . . ?
O4 C22 C21 120.1(4) . . ?
O3 C22 C21 115.5(4) . . ?
C27A O5A C28A 115.4(8) . . ?
C24A C23A C19 115.6(5) . . ?
C24A C23A H23A 108.4 . . ?
C19 C23A H23A 108.4 . . ?
C24A C23A H23B 108.4 . . ?
C19 C23A H23B 108.4 . . ?
H23A C23A H23B 107.4 . . ?
C23A C24A C25A 111.4(6) . . ?
C23A C24A H24A 109.4 . . ?
C25A C24A H24A 109.4 . . ?
C23A C24A H24B 109.4 . . ?
C25A C24A H24B 109.4 . . ?
H24A C24A H24B 108.0 . . ?
C24A C25A C26A 112.6(6) . . ?
C24A C25A H25A 109.1 . . ?
C26A C25A H25A 109.1 . . ?
C24A C25A H25B 109.1 . . ?
C26A C25A H25B 109.1 . . ?
H25A C25A H25B 107.8 . . ?
C27A C26A C25A 113.8(5) . . ?
C27A C26A H26A 108.8 . . ?
C25A C26A H26A 108.8 . . ?
C27A C26A H26B 108.8 . . ?
C25A C26A H26B 108.8 . . ?
H26A C26A H26B 107.7 . . ?
O6A C27A O5A 123.1(8) . . ?
O6A C27A C26A 123.9(7) . . ?
O5A C27A C26A 113.0(6) . . ?
O5A C28A H28A 109.5 . . ?
O5A C28A H28B 109.5 . . ?
H28A C28A H28B 109.5 . . ?
O5A C28A H28C 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C28B O5B C27B 115(2) . . ?
C19 C23B C24B 103.8(17) . . ?
C19 C23B H23C 111.0 . . ?
C24B C23B H23C 111.0 . . ?
C19 C23B H23D 111.0 . . ?
C24B C23B H23D 111.0 . . ?
H23C C23B H23D 109.0 . . ?
C23B C24B C25B 127(2) . . ?
C23B C24B H24C 105.5 . . ?
C25B C24B H24C 105.5 . . ?
C23B C24B H24D 105.5 . . ?
C25B C24B H24D 105.5 . . ?
H24C C24B H24D 106.0 . . ?
C26B C25B C24B 120(3) . . ?
C26B C25B H25C 107.3 . . ?
C24B C25B H25C 107.3 . . ?
C26B C25B H25D 107.3 . . ?
C24B C25B H25D 107.3 . . ?
H25C C25B H25D 106.9 . . ?
C25B C26B C27B 111(3) . . ?
C25B C26B H26C 109.3 . . ?
C27B C26B H26C 109.3 . . ?
C25B C26B H26D 109.3 . . ?
C27B C26B H26D 109.3 . . ?
H26C C26B H26D 108.0 . . ?
O6B C27B O5B 132(3) . . ?
O6B C27B C26B 116(3) . . ?
O5B C27B C26B 111(2) . . ?
O5B C28B H28D 109.5 . . ?
O5B C28B H28E 109.5 . . ?
H28D C28B H28E 109.5 . . ?
O5B C28B H28F 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
H7A O7A H7B 124.8 . . ?
H7C O7B H7D 123.3 . . ?

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
C5 N1 C1 C2 -0.1(7) . . . . ?
Ru1 N1 C1 C2 -176.5(4) . . . . ?
N1 C1 C2 C3 -0.6(8) . . . . ?
C1 C2 C3 C4 0.5(8) . . . . ?
C2 C3 C4 C5 0.2(8) . . . . ?
C1 N1 C5 C4 0.9(6) . . . . ?
Ru1 N1 C5 C4 177.7(3) . . . . ?
C1 N1 C5 C6 -177.8(4) . . . . ?
Ru1 N1 C5 C6 -0.9(5) . . . . ?
C3 C4 C5 N1 -1.0(7) . . . . ?
C3 C4 C5 C6 177.5(5) . . . . ?
C10 N2 C6 C7 1.0(6) . . . . ?
Ru1 N2 C6 C7 176.8(3) . . . . ?
C10 N2 C6 C5 -179.2(4) . . . . ?
Ru1 N2 C6 C5 -3.4(5) . . . . ?
N1 C5 C6 N2 2.7(6) . . . . ?
C4 C5 C6 N2 -175.9(4) . . . . ?
N1 C5 C6 C7 -177.6(4) . . . . ?
C4 C5 C6 C7 3.8(8) . . . . ?
N2 C6 C7 C8 -1.1(7) . . . . ?
C5 C6 C7 C8 179.1(5) . . . . ?
C6 C7 C8 C9 0.8(8) . . . . ?
C7 C8 C9 C10 -0.3(8) . . . . ?
C6 N2 C10 C9 -0.5(6) . . . . ?
Ru1 N2 C10 C9 -176.3(3) . . . . ?
C6 N2 C10 C11 179.0(4) . . . . ?
Ru1 N2 C10 C11 3.2(5) . . . . ?
C8 C9 C10 N2 0.1(7) . . . . ?
C8 C9 C10 C11 -179.3(4) . . . . ?
C15 N3 C11 C12 -0.5(6) . . . . ?
Ru1 N3 C11 C12 -179.7(3) . . . . ?
C15 N3 C11 C10 179.4(4) . . . . ?
Ru1 N3 C11 C10 0.2(4) . . . . ?
N2 C10 C11 N3 -2.1(5) . . . . ?
C9 C10 C11 N3 177.4(4) . . . . ?
N2 C10 C11 C12 177.8(4) . . . . ?
C9 C10 C11 C12 -2.8(7) . . . . ?
N3 C11 C12 C13 1.5(6) . . . . ?
C10 C11 C12 C13 -178.4(4) . . . . ?
C11 C12 C13 C14 -1.3(7) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C11 N3 C15 C14 -0.7(6) . . . . ?
Ru1 N3 C15 C14 178.3(3) . . . . ?
C13 C14 C15 N3 0.9(7) . . . . ?
Ru1 O1 C16 O2 177.1(3) . . . . ?
Ru1 O1 C16 C17 -1.6(4) . . . . ?
C21 N4 C17 C18 1.9(6) . . . . ?
Ru1 N4 C17 C18 -173.3(3) . . . . ?
C21 N4 C17 C16 178.3(3) . . . . ?
Ru1 N4 C17 C16 3.1(4) . . . . ?
O2 C16 C17 N4 -179.6(4) . . . . ?
O1 C16 C17 N4 -0.8(5) . . . . ?
O2 C16 C17 C18 -3.4(6) . . . . ?
O1 C16 C17 C18 175.4(4) . . . . ?
N4 C17 C18 C19 -0.6(6) . . . . ?
C16 C17 C18 C19 -176.5(4) . . . . ?
C17 C18 C19 C23B -162.5(13) . . . . ?
C17 C18 C19 C20 -1.4(7) . . . . ?
C17 C18 C19 C23A 170.6(5) . . . . ?
C23B C19 C20 C21 165.5(11) . . . . ?
C18 C19 C20 C21 2.2(7) . . . . ?
C23A C19 C20 C21 -169.6(5) . . . . ?
C17 N4 C21 C20 -1.1(6) . . . . ?
Ru1 N4 C21 C20 174.1(3) . . . . ?
C17 N4 C21 C22 -179.0(3) . . . . ?
Ru1 N4 C21 C22 -3.8(4) . . . . ?
C19 C20 C21 N4 -1.0(6) . . . . ?
C19 C20 C21 C22 176.5(4) . . . . ?
Ru1 O3 C22 O4 177.5(3) . . . . ?
Ru1 O3 C22 C21 -2.6(4) . . . . ?
N4 C21 C22 O4 -176.0(3) . . . . ?
C20 C21 C22 O4 6.3(6) . . . . ?
N4 C21 C22 O3 4.1(5) . . . . ?
C20 C21 C22 O3 -173.5(4) . . . . ?
C20 C19 C23A C24A -13.4(8) . . . . ?
C18 C19 C23A C24A 174.9(5) . . . . ?
C19 C23A C24A C25A -177.1(5) . . . . ?
C23A C24A C25A C26A -72.4(8) . . . . ?
C24A C25A C26A C27A -165.7(6) . . . . ?
C28A O5A C27A O6A 0.2(15) . . . . ?
C28A O5A C27A C26A -178.1(8) . . . . ?
C25A C26A C27A O6A -15.1(12) . . . . ?
C25A C26A C27A O5A 163.2(8) . . . . ?
C20 C19 C23B C24B 80.8(17) . . . . ?
C18 C19 C23B C24B -117.4(14) . . . . ?
C19 C23B C24B C25B 179(2) . . . . ?
C23B C24B C25B C26B -70(5) . . . . ?
C24B C25B C26B C27B -170(3) . . . . ?
C28B O5B C27B O6B 7(5) . . . . ?
C28B O5B C27B C26B 170(2) . . . . ?
C25B C26B C27B O6B -99(5) . . . . ?
C25B C26B C27B O5B 94(4) . . . . ?

_refine_diff_density_max         0.810
_refine_diff_density_min         -0.931
_refine_diff_density_rms         0.101


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMF/EtOAc
