#------------------------------------------------------------------------------
#$Date: 2026-03-04 12:11:27 +0100 (Wed 04 de Mar de 2026) $
#$Revision: 304742 $
#$URL: svn://www.crystallography.net/cod/cif/7/72/04/7720425.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_7720425
loop_
_publ_author_name
'Rosner, Alexander'
'Geisler, Heiko'
'Hejl, Michaela'
'Gradl, Mathias'
'Legin, Anton A.'
'Prado-Roller, Alexander'
'Jakupec, Michael A.'
'Heffeter, Petra'
'Berger, Walter'
'Keppler, Bernhard K.'
'Kandioller, Wolfgang'
_publ_section_title
;
 Naphthoquinone-derived tridentate Ru(II) and Os(II) organometallics with
 exceptional cytotoxicity: synthesis, characterization, stability in
 aqueous solution and biological in vitro evaluation.
;
_journal_issue                   5
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2254
_journal_page_last               2268
_journal_paper_doi               10.1039/d5dt01649e
_journal_volume                  55
_journal_year                    2026
_chemical_formula_moiety         'C27 H30 N2 O3 Ru, C4 H10 O'
_chemical_formula_sum            'C31 H40 N2 O4 Ru'
_chemical_formula_weight         605.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-05-26
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.05.22 svn.r631f81ec for OlexSys, GUI svn.r7248)
;
_audit_update_record
;
2025-07-01 deposited with the CCDC.	2025-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                103.754(8)
_cell_angle_beta                 100.413(8)
_cell_angle_gamma                112.528(8)
_cell_formula_units_Z            2
_cell_length_a                   9.7041(11)
_cell_length_b                   12.6241(15)
_cell_length_c                   14.1057(14)
_cell_measurement_reflns_used    9356
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.75
_cell_measurement_theta_min      1.54
_cell_volume                     1477.5(3)
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_collection       'X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)'
_computing_data_reduction
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0673
_diffrn_reflns_av_unetI/netI     0.1639
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30235
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.840
_diffrn_reflns_theta_min         2.384
_diffrn_source                   'Axo Mo'
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.5908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.981
_refine_diff_density_min         -1.384
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         7146
_refine_ls_number_restraints     395
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0349P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4092
_reflns_number_total             7146
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5dt01649e2.cif
_cod_data_source_block           alro129
_cod_database_code               7720425
_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.
;
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.930
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.69090(3) 0.45964(3) 0.13261(2) 0.01794(10) Uani 1 1 d . . . . .
O1 O 0.1048(2) 0.42418(19) 0.29723(14) 0.0233(5) Uani 1 1 d . . . . .
O2 O 0.4645(2) 0.35646(18) 0.13906(14) 0.0208(5) Uani 1 1 d . . . . .
O3 O 0.6204(2) 0.59048(18) 0.18436(14) 0.0188(5) Uani 1 1 d . . . . .
N1 N 0.6616(3) 0.5437(2) 0.33183(17) 0.0178(6) Uani 1 1 d . . . . .
N2 N 0.7466(3) 0.4936(2) 0.29036(18) 0.0206(6) Uani 1 1 d . . . . .
C1 C 0.6832(4) 0.3081(3) 0.0145(2) 0.0243(8) Uani 1 1 d . . . . .
C2 C 0.6342(4) 0.3822(3) -0.0325(2) 0.0269(8) Uani 1 1 d . . . . .
H2 H 0.523071 0.347099 -0.075841 0.032 Uiso 1 1 calc R U . . .
C3 C 0.7256(4) 0.5061(3) -0.0012(2) 0.0272(8) Uani 1 1 d . . . . .
H3 H 0.677571 0.557066 -0.023082 0.033 Uiso 1 1 calc R U . . .
C4 C 0.8719(4) 0.5659(3) 0.0768(2) 0.0265(8) Uani 1 1 d . . . . .
C5 C 0.9223(4) 0.4935(3) 0.1211(2) 0.0237(8) Uani 1 1 d . . . . .
H5 H 1.012567 0.534497 0.185463 0.028 Uiso 1 1 calc R U . . .
C6 C 0.8300(4) 0.3662(3) 0.0904(2) 0.0225(8) Uani 1 1 d . . . . .
H6 H 0.857031 0.320704 0.133946 0.027 Uiso 1 1 calc R U . . .
C7 C 0.5806(4) 0.1729(3) -0.0133(3) 0.0376(9) Uani 1 1 d . . . . .
H7 H 0.596632 0.151800 0.050446 0.045 Uiso 1 1 calc R U . . .
C8 C 0.6377(5) 0.1023(3) -0.0895(3) 0.0638(13) Uani 1 1 d . . . . .
H8A H 0.573516 0.014498 -0.107435 0.096 Uiso 1 1 calc R U . . .
H8B H 0.747388 0.123107 -0.057651 0.096 Uiso 1 1 calc R U . . .
H8C H 0.628345 0.124462 -0.151523 0.096 Uiso 1 1 calc R U . . .
C9 C 0.4056(4) 0.1313(4) -0.0577(3) 0.0587(12) Uani 1 1 d . . . . .
H9A H 0.385245 0.144614 -0.123426 0.088 Uiso 1 1 calc R U . . .
H9B H 0.370858 0.178184 -0.010035 0.088 Uiso 1 1 calc R U . . .
H9C H 0.348147 0.044455 -0.068048 0.088 Uiso 1 1 calc R U . . .
C10 C 0.9633(5) 0.7024(3) 0.1135(3) 0.0490(11) Uani 1 1 d . . . . .
H10A H 1.009821 0.727132 0.061443 0.074 Uiso 1 1 calc R U . . .
H10B H 1.046445 0.729542 0.177412 0.074 Uiso 1 1 calc R U . . .
H10C H 0.893093 0.739526 0.125450 0.074 Uiso 1 1 calc R U . . .
C11 C 0.8320(4) 0.4775(3) 0.3660(2) 0.0247(8) Uani 1 1 d . . . . .
H11 H 0.906017 0.446272 0.359637 0.030 Uiso 1 1 calc R U . . .
C12 C 0.7960(4) 0.5137(3) 0.4560(2) 0.0313(9) Uani 1 1 d . . . . .
H12 H 0.838168 0.510426 0.520842 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6864(4) 0.5553(3) 0.4314(2) 0.0240(8) Uani 1 1 d . . . . .
H13 H 0.638051 0.586216 0.476189 0.029 Uiso 1 1 calc R U . . .
C14 C 0.4204(4) 0.4230(3) 0.2001(2) 0.0183(7) Uani 1 1 d . . . . .
C15 C 0.5448(4) 0.5541(3) 0.2519(2) 0.0177(7) Uani 1 1 d . . . . .
C16 C 0.4884(4) 0.6409(3) 0.3052(2) 0.0186(7) Uani 1 1 d . . . . .
C17 C 0.5824(4) 0.7643(3) 0.3395(2) 0.0263(8) Uani 1 1 d . . . . .
H17 H 0.681744 0.794914 0.328231 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5326(4) 0.8445(3) 0.3905(2) 0.0352(9) Uani 1 1 d . . . . .
H18 H 0.597913 0.929826 0.414435 0.042 Uiso 1 1 calc R U . . .
C19 C 0.3874(4) 0.7994(3) 0.4062(2) 0.0331(9) Uani 1 1 d . . . . .
H19 H 0.353366 0.853909 0.441583 0.040 Uiso 1 1 calc R U . . .
C20 C 0.2917(4) 0.6751(3) 0.3704(2) 0.0256(8) Uani 1 1 d . . . . .
H20 H 0.191898 0.644996 0.381053 0.031 Uiso 1 1 calc R U . . .
C21 C 0.3399(4) 0.5937(3) 0.3189(2) 0.0183(7) Uani 1 1 d . . . . .
C22 C 0.2336(4) 0.4602(3) 0.2789(2) 0.0171(7) Uani 1 1 d . . . . .
C23 C 0.2767(4) 0.3782(3) 0.2168(2) 0.0198(7) Uani 1 1 d . . . . .
C24 C 0.1655(4) 0.2451(3) 0.1701(2) 0.0279(8) Uani 1 1 d D . . . .
H24C H 0.188453 0.210573 0.107541 0.034 Uiso 0.481(14) 1 calc R U P A 2
H24D H 0.057692 0.236484 0.148756 0.034 Uiso 0.481(14) 1 calc R U P A 2
H24A H 0.143641 0.220901 0.094802 0.034 Uiso 0.519(14) 1 calc R U P A 1
H24B H 0.065436 0.232181 0.184785 0.034 Uiso 0.519(14) 1 calc R U P A 1
C25 C 0.2251(12) 0.1610(8) 0.2085(7) 0.027(2) Uani 0.519(14) 1 d . . P A 1
H25 H 0.318301 0.164872 0.185775 0.032 Uiso 0.519(14) 1 calc R U P A 1
C26 C 0.2719(13) 0.2030(8) 0.3262(7) 0.040(3) Uani 0.519(14) 1 d D . P A 1
H26A H 0.355985 0.286594 0.354667 0.060 Uiso 0.519(14) 1 calc R U P A 1
H26B H 0.181042 0.200305 0.348524 0.060 Uiso 0.519(14) 1 calc R U P A 1
H26C H 0.308470 0.148943 0.350311 0.060 Uiso 0.519(14) 1 calc R U P A 1
C27 C 0.0948(16) 0.0316(11) 0.1617(11) 0.041(3) Uani 0.519(14) 1 d . . P A 1
H27A H 0.066991 0.006785 0.086862 0.061 Uiso 0.519(14) 1 calc R U P A 1
H27B H 0.130424 -0.023427 0.184934 0.061 Uiso 0.519(14) 1 calc R U P A 1
H27C H 0.002997 0.027935 0.183147 0.061 Uiso 0.519(14) 1 calc R U P A 1
C25Z C 0.1708(14) 0.1704(9) 0.2391(9) 0.042(3) Uani 0.481(14) 1 d . . P A 2
H25Z H 0.143446 0.206756 0.299700 0.051 Uiso 0.481(14) 1 calc R U P A 2
C26Z C 0.3247(14) 0.1764(11) 0.2812(12) 0.066(4) Uani 0.481(14) 1 d . . P A 2
H26D H 0.315777 0.125372 0.324526 0.099 Uiso 0.481(14) 1 calc R U P A 2
H26E H 0.361549 0.147001 0.224919 0.099 Uiso 0.481(14) 1 calc R U P A 2
H26F H 0.399333 0.260943 0.322170 0.099 Uiso 0.481(14) 1 calc R U P A 2
C27Z C 0.046(2) 0.0387(13) 0.1912(15) 0.088(6) Uani 0.481(14) 1 d D . P A 2
H27D H -0.055938 0.036814 0.163721 0.131 Uiso 0.481(14) 1 calc R U P A 2
H27E H 0.072322 -0.004788 0.135710 0.131 Uiso 0.481(14) 1 calc R U P A 2
H27F H 0.039574 -0.000763 0.243396 0.131 Uiso 0.481(14) 1 calc R U P A 2
O1S O 0.8549(4) 1.1259(2) 0.4639(2) 0.0709(10) Uani 1 1 d . . . . .
C1S C 0.7236(7) 1.1433(4) 0.3153(3) 0.096(2) Uani 1 1 d . . . . .
H1SA H 0.764710 1.169369 0.261923 0.144 Uiso 1 1 calc R U . . .
H1SB H 0.644673 1.171543 0.325782 0.144 Uiso 1 1 calc R U . . .
H1SC H 0.675748 1.054196 0.294181 0.144 Uiso 1 1 calc R U . . .
C2S C 0.8482(6) 1.1940(4) 0.4085(4) 0.0770(16) Uani 1 1 d . . . . .
H2SA H 0.947834 1.223651 0.391577 0.092 Uiso 1 1 calc R U . . .
H2SB H 0.844167 1.266264 0.451984 0.092 Uiso 1 1 calc R U . . .
C3S C 0.9801(5) 1.1730(4) 0.5569(3) 0.0554(12) Uani 1 1 d . . . . .
H3SA H 1.079253 1.188044 0.540243 0.066 Uiso 1 1 calc R U . . .
H3SB H 0.990567 1.252047 0.599351 0.066 Uiso 1 1 calc R U . . .
C4S C 0.9562(6) 1.0928(4) 0.6143(4) 0.0852(16) Uani 1 1 d . . . . .
H4SA H 1.044653 1.128992 0.676934 0.128 Uiso 1 1 calc R U . . .
H4SB H 0.859324 1.078982 0.632292 0.128 Uiso 1 1 calc R U . . .
H4SC H 0.948020 1.014973 0.573178 0.128 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
O2 Ru1 C1 93.46(10) . . ?
O2 Ru1 C2 95.54(11) . . ?
O2 Ru1 C3 121.37(11) . . ?
O2 Ru1 C4 159.28(10) . . ?
O2 Ru1 C5 156.23(11) . . ?
O2 Ru1 C6 118.83(11) . . ?
O3 Ru1 O2 77.21(8) . . ?
O3 Ru1 N2 76.65(8) . . ?
O3 Ru1 C1 152.97(10) . . ?
O3 Ru1 C2 116.35(10) . . ?
O3 Ru1 C3 94.40(10) . . ?
O3 Ru1 C4 97.43(10) . . ?
O3 Ru1 C5 125.67(11) . . ?
O3 Ru1 C6 163.58(11) . . ?
N2 Ru1 O2 81.65(9) . . ?
N2 Ru1 C1 127.64(11) . . ?
N2 Ru1 C2 165.90(11) . . ?
N2 Ru1 C3 153.30(12) . . ?
N2 Ru1 C4 116.96(12) . . ?
N2 Ru1 C5 96.56(11) . . ?
N2 Ru1 C6 101.11(10) . . ?
C2 Ru1 C1 38.46(11) . . ?
C2 Ru1 C6 68.04(12) . . ?
C3 Ru1 C1 68.61(12) . . ?
C3 Ru1 C2 37.12(12) . . ?
C3 Ru1 C4 38.37(12) . . ?
C3 Ru1 C5 68.01(12) . . ?
C3 Ru1 C6 80.35(12) . . ?
C4 Ru1 C1 82.31(12) . . ?
C4 Ru1 C2 68.61(13) . . ?
C4 Ru1 C6 68.80(12) . . ?
C5 Ru1 C1 68.75(12) . . ?
C5 Ru1 C2 80.41(12) . . ?
C5 Ru1 C4 37.82(11) . . ?
C5 Ru1 C6 37.98(12) . . ?
C6 Ru1 C1 37.73(11) . . ?
C14 O2 Ru1 111.65(19) . . ?
C15 O3 Ru1 104.56(17) . . ?
N2 N1 C15 112.3(2) . . ?
C13 N1 N2 111.2(2) . . ?
C13 N1 C15 135.6(2) . . ?
N1 N2 Ru1 111.03(17) . . ?
C11 N2 Ru1 142.2(2) . . ?
C11 N2 N1 106.6(2) . . ?
C2 C1 Ru1 70.38(17) . . ?
C2 C1 C7 122.0(3) . . ?
C6 C1 Ru1 70.91(17) . . ?
C6 C1 C2 117.6(3) . . ?
C6 C1 C7 120.4(3) . . ?
C7 C1 Ru1 128.4(2) . . ?
Ru1 C2 H2 118.9 . . ?
C1 C2 Ru1 71.16(17) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 Ru1 70.49(18) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 118.9 . . ?
Ru1 C3 H3 118.2 . . ?
C2 C3 Ru1 72.40(18) . . ?
C2 C3 H3 118.2 . . ?
C2 C3 C4 122.2(3) . . ?
C4 C3 Ru1 71.54(17) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 Ru1 70.09(18) . . ?
C3 C4 C10 120.5(3) . . ?
C5 C4 Ru1 70.90(18) . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 C10 122.0(3) . . ?
C10 C4 Ru1 127.0(2) . . ?
Ru1 C5 H5 118.6 . . ?
C4 C5 Ru1 71.28(18) . . ?
C4 C5 H5 118.6 . . ?
C4 C5 C6 121.3(3) . . ?
C6 C5 Ru1 71.58(18) . . ?
C6 C5 H5 118.6 . . ?
Ru1 C6 H6 118.8 . . ?
C1 C6 Ru1 71.35(17) . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 H6 118.8 . . ?
C5 C6 Ru1 70.44(17) . . ?
C5 C6 H6 118.8 . . ?
C1 C7 H7 107.7 . . ?
C1 C7 C8 108.4(3) . . ?
C1 C7 C9 115.2(3) . . ?
C8 C7 H7 107.7 . . ?
C9 C7 H7 107.7 . . ?
C9 C7 C8 109.9(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11 125.3 . . ?
N2 C11 C12 109.5(3) . . ?
C12 C11 H11 125.3 . . ?
C11 C12 H12 127.0 . . ?
C13 C12 C11 105.9(3) . . ?
C13 C12 H12 127.0 . . ?
N1 C13 C12 106.7(3) . . ?
N1 C13 H13 126.6 . . ?
C12 C13 H13 126.6 . . ?
O2 C14 C15 112.9(3) . . ?
O2 C14 C23 123.3(3) . . ?
C23 C14 C15 123.8(3) . . ?
O3 C15 N1 106.1(2) . . ?
O3 C15 C14 109.1(2) . . ?
O3 C15 C16 114.5(2) . . ?
N1 C15 C14 102.5(2) . . ?
C16 C15 N1 108.6(2) . . ?
C16 C15 C14 114.9(3) . . ?
C17 C16 C15 119.9(3) . . ?
C17 C16 C21 121.0(3) . . ?
C21 C16 C15 119.2(3) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.7(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C22 121.8(3) . . ?
C20 C21 C16 118.2(3) . . ?
C20 C21 C22 120.0(3) . . ?
O1 C22 C21 118.3(3) . . ?
O1 C22 C23 122.0(3) . . ?
C23 C22 C21 119.7(3) . . ?
C14 C23 C22 119.3(3) . . ?
C14 C23 C24 120.6(3) . . ?
C22 C23 C24 120.0(3) . . ?
C23 C24 H24C 108.5 . . ?
C23 C24 H24D 108.5 . . ?
C23 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C23 C24 C25 114.5(4) . . ?
C23 C24 C25Z 115.2(5) . . ?
H24C C24 H24D 107.5 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C25Z C24 H24C 108.5 . . ?
C25Z C24 H24D 108.5 . . ?
C24 C25 H25 109.4 . . ?
C26 C25 C24 109.6(8) . . ?
C26 C25 H25 109.4 . . ?
C27 C25 C24 108.1(8) . . ?
C27 C25 H25 109.4 . . ?
C27 C25 C26 110.9(8) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C24 C25Z H25Z 105.5 . . ?
C24 C25Z C27Z 112.8(10) . . ?
C26Z C25Z C24 115.8(11) . . ?
C26Z C25Z H25Z 105.5 . . ?
C26Z C25Z C27Z 110.9(10) . . ?
C27Z C25Z H25Z 105.5 . . ?
C25Z C26Z H26D 109.5 . . ?
C25Z C26Z H26E 109.5 . . ?
C25Z C26Z H26F 109.5 . . ?
H26D C26Z H26E 109.5 . . ?
H26D C26Z H26F 109.5 . . ?
H26E C26Z H26F 109.5 . . ?
C25Z C27Z H27D 109.5 . . ?
C25Z C27Z H27E 109.5 . . ?
C25Z C27Z H27F 109.5 . . ?
H27D C27Z H27E 109.5 . . ?
H27D C27Z H27F 109.5 . . ?
H27E C27Z H27F 109.5 . . ?
C2S O1S C3S 120.5(4) . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
O1S C2S C1S 119.0(5) . . ?
O1S C2S H2SA 107.6 . . ?
O1S C2S H2SB 107.6 . . ?
C1S C2S H2SA 107.6 . . ?
C1S C2S H2SB 107.6 . . ?
H2SA C2S H2SB 107.0 . . ?
O1S C3S H3SA 109.1 . . ?
O1S C3S H3SB 109.1 . . ?
H3SA C3S H3SB 107.8 . . ?
C4S C3S O1S 112.6(4) . . ?
C4S C3S H3SA 109.1 . . ?
C4S C3S H3SB 109.1 . . ?
C3S C4S H4SA 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
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 O2 2.114(2) . ?
Ru1 O3 2.0503(19) . ?
Ru1 N2 2.088(2) . ?
Ru1 C1 2.184(3) . ?
Ru1 C2 2.174(3) . ?
Ru1 C3 2.150(3) . ?
Ru1 C4 2.169(3) . ?
Ru1 C5 2.164(3) . ?
Ru1 C6 2.178(3) . ?
O1 C22 1.255(3) . ?
O2 C14 1.302(3) . ?
O3 C15 1.363(3) . ?
N1 N2 1.350(3) . ?
N1 C13 1.343(3) . ?
N1 C15 1.515(4) . ?
N2 C11 1.334(3) . ?
C1 C2 1.435(4) . ?
C1 C6 1.411(4) . ?
C1 C7 1.516(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.376(4) . ?
C3 H3 1.0000 . ?
C3 C4 1.419(4) . ?
C4 C5 1.404(4) . ?
C4 C10 1.505(5) . ?
C5 H5 1.0000 . ?
C5 C6 1.413(4) . ?
C6 H6 1.0000 . ?
C7 H7 1.0000 . ?
C7 C8 1.547(4) . ?
C7 C9 1.526(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.396(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.519(4) . ?
C14 C23 1.378(4) . ?
C15 C16 1.511(4) . ?
C16 C17 1.373(4) . ?
C16 C21 1.403(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.389(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(4) . ?
C21 C22 1.492(4) . ?
C22 C23 1.430(4) . ?
C23 C24 1.500(4) . ?
C24 H24C 0.9900 . ?
C24 H24D 0.9900 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.545(10) . ?
C24 C25Z 1.516(11) . ?
C25 H25 1.0000 . ?
C25 C26 1.539(14) . ?
C25 C27 1.519(15) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C25Z H25Z 1.0000 . ?
C25Z C26Z 1.469(18) . ?
C25Z C27Z 1.523(17) . ?
C26Z H26D 0.9800 . ?
C26Z H26E 0.9800 . ?
C26Z H26F 0.9800 . ?
C27Z H27D 0.9800 . ?
C27Z H27E 0.9800 . ?
C27Z H27F 0.9800 . ?
O1S C2S 1.303(5) . ?
O1S C3S 1.432(5) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C1S C2S 1.426(6) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S C4S 1.418(5) . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
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
Ru1 O2 C14 C15 -1.8(3) . . . . ?
Ru1 O2 C14 C23 179.0(2) . . . . ?
Ru1 O3 C15 N1 57.1(2) . . . . ?
Ru1 O3 C15 C14 -52.7(2) . . . . ?
Ru1 O3 C15 C16 177.0(2) . . . . ?
Ru1 N2 C11 C12 -172.8(3) . . . . ?
Ru1 C1 C2 C3 52.2(3) . . . . ?
Ru1 C1 C6 C5 -52.3(2) . . . . ?
Ru1 C1 C7 C8 -170.9(3) . . . . ?
Ru1 C1 C7 C9 65.5(4) . . . . ?
Ru1 C2 C3 C4 53.7(3) . . . . ?
Ru1 C3 C4 C5 54.6(2) . . . . ?
Ru1 C3 C4 C10 -122.0(3) . . . . ?
Ru1 C4 C5 C6 53.4(3) . . . . ?
Ru1 C5 C6 C1 52.7(2) . . . . ?
O1 C22 C23 C14 -179.4(3) . . . . ?
O1 C22 C23 C24 0.9(4) . . . . ?
O2 C14 C15 O3 37.4(3) . . . . ?
O2 C14 C15 N1 -74.9(3) . . . . ?
O2 C14 C15 C16 167.5(2) . . . . ?
O2 C14 C23 C22 -175.1(2) . . . . ?
O2 C14 C23 C24 4.6(4) . . . . ?
O3 C15 C16 C17 -41.5(4) . . . . ?
O3 C15 C16 C21 138.4(3) . . . . ?
N1 N2 C11 C12 2.3(4) . . . . ?
N1 C15 C16 C17 77.0(3) . . . . ?
N1 C15 C16 C21 -103.1(3) . . . . ?
N2 N1 C13 C12 1.6(4) . . . . ?
N2 N1 C15 O3 -40.7(3) . . . . ?
N2 N1 C15 C14 73.7(3) . . . . ?
N2 N1 C15 C16 -164.3(2) . . . . ?
N2 C11 C12 C13 -1.3(4) . . . . ?
C1 C2 C3 Ru1 -52.6(3) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C2 C1 C6 Ru1 54.4(2) . . . . ?
C2 C1 C6 C5 2.1(4) . . . . ?
C2 C1 C7 C8 99.8(4) . . . . ?
C2 C1 C7 C9 -23.9(4) . . . . ?
C2 C3 C4 Ru1 -54.0(3) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C2 C3 C4 C10 -176.0(3) . . . . ?
C3 C4 C5 Ru1 -54.2(2) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 Ru1 -53.2(3) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C6 C1 C2 Ru1 -54.7(2) . . . . ?
C6 C1 C2 C3 -2.4(4) . . . . ?
C6 C1 C7 C8 -82.0(4) . . . . ?
C6 C1 C7 C9 154.4(3) . . . . ?
C7 C1 C2 Ru1 123.6(3) . . . . ?
C7 C1 C2 C3 175.9(3) . . . . ?
C7 C1 C6 Ru1 -123.9(3) . . . . ?
C7 C1 C6 C5 -176.2(3) . . . . ?
C10 C4 C5 Ru1 122.4(3) . . . . ?
C10 C4 C5 C6 175.7(3) . . . . ?
C11 C12 C13 N1 -0.2(4) . . . . ?
C13 N1 N2 Ru1 174.3(2) . . . . ?
C13 N1 N2 C11 -2.5(3) . . . . ?
C13 N1 C15 O3 151.2(3) . . . . ?
C13 N1 C15 C14 -94.4(4) . . . . ?
C13 N1 C15 C16 27.6(5) . . . . ?
C14 C15 C16 C17 -169.0(3) . . . . ?
C14 C15 C16 C21 10.9(4) . . . . ?
C14 C23 C24 C25 64.0(5) . . . . ?
C14 C23 C24 C25Z 96.0(6) . . . . ?
C15 N1 N2 Ru1 3.2(3) . . . . ?
C15 N1 N2 C11 -173.6(2) . . . . ?
C15 N1 C13 C12 169.8(3) . . . . ?
C15 C14 C23 C22 5.8(4) . . . . ?
C15 C14 C23 C24 -174.5(3) . . . . ?
C15 C16 C17 C18 -178.7(3) . . . . ?
C15 C16 C21 C20 178.5(3) . . . . ?
C15 C16 C21 C22 -2.2(4) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C16 C21 C22 O1 177.4(3) . . . . ?
C16 C21 C22 C23 -5.9(4) . . . . ?
C17 C16 C21 C20 -1.5(4) . . . . ?
C17 C16 C21 C22 177.7(3) . . . . ?
C17 C18 C19 C20 -0.6(5) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C19 C20 C21 C16 0.6(4) . . . . ?
C19 C20 C21 C22 -178.7(3) . . . . ?
C20 C21 C22 O1 -3.3(4) . . . . ?
C20 C21 C22 C23 173.3(3) . . . . ?
C21 C16 C17 C18 1.4(5) . . . . ?
C21 C22 C23 C14 4.1(4) . . . . ?
C21 C22 C23 C24 -175.6(3) . . . . ?
C22 C23 C24 C25 -116.2(5) . . . . ?
C22 C23 C24 C25Z -84.3(6) . . . . ?
C23 C14 C15 O3 -143.4(3) . . . . ?
C23 C14 C15 N1 104.4(3) . . . . ?
C23 C14 C15 C16 -13.2(4) . . . . ?
C23 C24 C25 C26 54.1(9) . . . . ?
C23 C24 C25 C27 175.0(5) . . . . ?
C23 C24 C25Z C26Z -56.1(14) . . . . ?
C23 C24 C25Z C27Z 174.8(7) . . . . ?
C2S O1S C3S C4S 171.3(4) . . . . ?
C3S O1S C2S C1S 178.8(4) . . . . ?
