#------------------------------------------------------------------------------
#$Date: 2022-05-05 23:18:04 +0300 (Thu, 05 May 2022) $
#$Revision: 274939 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566090.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_1566090
loop_
_publ_author_name
'Bühler, Jan'
'Zurflüh, Jonas'
'Siol, Sebastian'
'Blacque, Olivier'
'Sévery, Laurent'
'Tilley, S. David'
_publ_section_title
;
 Electrochemical ruthenium-catalysed C--H activation in water through
 heterogenization of a molecular catalyst
;
_journal_issue                   5
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              1512
_journal_page_last               1519
_journal_paper_doi               10.1039/D1CY01999F
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C21 H16 Cl N4 O5 P Ru'
_chemical_formula_sum            'C21 H16 Cl N4 O5 P Ru'
_chemical_formula_weight         571.87
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-07-05 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0515(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.06525(17)
_cell_length_b                   25.1567(4)
_cell_length_c                   13.9309(2)
_cell_measurement_reflns_used    12726
_cell_measurement_temperature    160(1)
_cell_measurement_theta_max      78.6050
_cell_measurement_theta_min      3.6240
_cell_volume                     4853.59(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -128.00 -35.00   0.50    5.00    --  -49.87 -34.00 149.00  186
  2  ω    -65.00  29.00   0.50    5.00    --  -49.87  34.00 -52.00  188
  3  ω   -167.00 -73.00   0.50   20.00    --  -88.50 -34.00 149.00  188
  4  ω   -103.00 -10.00   0.50   20.00    --  -88.50  34.00 -52.00  186
  5  ω     95.00 178.00   0.50   20.00    --  110.00  34.00 -52.00  166
  6  ω     32.00 125.00   0.50   20.00    --  110.00 -34.00 149.00  186
  7  ω   -125.00 -73.00   0.50    5.00    --  -49.87-125.00-120.00  104
  8  ω   -125.00 -73.00   0.50    5.00    --  -49.87-125.00 -90.00  104
  9  ω     35.00 128.00   0.50    5.00    --   49.87  34.00 -52.00  186
 10  ω    -83.00 -11.00   0.50   20.00    --  -88.50 111.00  30.00  144
 11  ω     94.00 178.00   0.50   20.00    --  110.00  15.00  60.00  168
 12  ω     31.00 125.00   0.50   20.00    --  110.00 -30.00  30.00  188
 13  ω     31.00 125.00   0.50   20.00    --  110.00 -30.00 -60.00  188
 14  ω     62.00 146.00   0.50   20.00    --  110.00 178.00-180.00  168
 15  ω     34.00 107.00   0.50   20.00    --  110.00 -94.00 120.00  146
 16  ω     34.00 107.00   0.50   20.00    --  110.00 -94.00-180.00  146
 17  ω     48.00  78.00   0.50   20.00    --  110.00 -61.00  30.00   60
 18  ω     83.00 109.00   0.50   20.00    --  110.00 -61.00  30.00   52
 19  ω    104.00 176.00   0.50   20.00    --  110.00  45.00 -90.00  144
 20  ω     44.00  70.00   0.50   20.00    --  110.00 -94.00-150.00   52
 21  ω     36.00 108.00   0.50   20.00    --  110.00-111.00 120.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0182675000
_diffrn_orient_matrix_UB_12      0.0175411000
_diffrn_orient_matrix_UB_13      -0.1011823000
_diffrn_orient_matrix_UB_21      -0.1048577000
_diffrn_orient_matrix_UB_22      0.0199747000
_diffrn_orient_matrix_UB_23      -0.0256800000
_diffrn_orient_matrix_UB_31      0.0321307000
_diffrn_orient_matrix_UB_32      0.0551950000
_diffrn_orient_matrix_UB_33      0.0414438000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24717
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.498
_diffrn_reflns_theta_min         3.514
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    7.208
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.517
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_description       needle
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.015
_refine_diff_density_max         2.404
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.157
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1028P)²+1.5763P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1359
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4067
_reflns_number_total             4949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cy01999f2.cif
_cod_data_source_block           3
_cod_depositor_comments          'Adding full bibliography for 1566090.cif.'
_cod_original_cell_volume        4853.58(13)
_cod_database_code               1566090
_shelx_shelxl_version_number     2018/3
_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   0.900
_shelx_estimated_absorpt_t_min   0.374
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C18(H18), C20(H20), C21(H21)
;
loop_
_space_group_symop_operation_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_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
C1 C 0.3935(3) 0.6442(2) 0.4446(4) 0.0579(12) Uani 1 1 d . . . . .
H1 H 0.348083 0.667589 0.465276 0.069 Uiso 1 1 calc R U . . .
C2 C 0.4836(4) 0.6634(2) 0.4357(5) 0.0737(16) Uani 1 1 d . . . . .
H2 H 0.498909 0.699874 0.447583 0.088 Uiso 1 1 calc R U . . .
C3 C 0.5511(3) 0.6290(2) 0.4093(5) 0.0671(14) Uani 1 1 d . . . . .
H3 H 0.613899 0.641393 0.404824 0.081 Uiso 1 1 calc R U . . .
C4 C 0.5271(3) 0.5768(2) 0.3897(4) 0.0543(11) Uani 1 1 d . . . . .
H4 H 0.573033 0.552975 0.371208 0.065 Uiso 1 1 calc R U . . .
C5 C 0.4350(3) 0.55905(17) 0.3972(3) 0.0438(9) Uani 1 1 d . . . . .
C6 C 0.4011(3) 0.50500(17) 0.3771(3) 0.0413(8) Uani 1 1 d . . . . .
C7 C 0.4541(3) 0.46106(19) 0.3592(3) 0.0469(9) Uani 1 1 d . . . . .
H7 H 0.521154 0.464193 0.357897 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4080(3) 0.4121(2) 0.3429(4) 0.0544(11) Uani 1 1 d . . . . .
H8 H 0.443444 0.381817 0.328841 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3106(3) 0.40740(19) 0.3472(3) 0.0516(10) Uani 1 1 d . . . . .
H9 H 0.279426 0.373847 0.337403 0.062 Uiso 1 1 calc R U . . .
C10 C 0.2598(3) 0.45144(17) 0.3658(3) 0.0428(9) Uani 1 1 d . . . . .
C11 C 0.1563(3) 0.45543(19) 0.3732(3) 0.0453(9) Uani 1 1 d . . . . .
C12 C 0.0942(3) 0.4123(2) 0.3635(4) 0.0550(11) Uani 1 1 d . . . . .
H12 H 0.117604 0.377698 0.353297 0.066 Uiso 1 1 calc R U . . .
C13 C -0.0023(3) 0.4198(3) 0.3688(4) 0.0625(14) Uani 1 1 d . . . . .
H13 H -0.045106 0.390410 0.364983 0.075 Uiso 1 1 calc R U . . .
C14 C -0.0349(3) 0.4703(2) 0.3797(4) 0.0610(13) Uani 1 1 d . . . . .
H14 H -0.101572 0.476580 0.379642 0.073 Uiso 1 1 calc R U . . .
C15 C 0.0294(3) 0.5119(2) 0.3908(3) 0.0527(11) Uani 1 1 d . . . . .
H15 H 0.005959 0.546798 0.398075 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1279(3) 0.65834(19) 0.3934(3) 0.0483(10) Uani 1 1 d . . . . .
C17 C 0.1519(3) 0.64544(18) 0.2957(3) 0.0450(9) Uani 1 1 d . . . . .
C18 C 0.1317(3) 0.67876(19) 0.2163(3) 0.0486(10) Uani 1 1 d . . . . .
H18 H 0.101951 0.712208 0.222183 0.058 Uiso 1 1 calc R U . . .
C19 C 0.1549(3) 0.66348(18) 0.1286(3) 0.0461(9) Uani 1 1 d . . . . .
C20 C 0.1945(3) 0.61343(18) 0.1213(3) 0.0461(9) Uani 1 1 d . . . . .
H20 H 0.208020 0.601150 0.060555 0.055 Uiso 1 1 calc R U . . .
C21 C 0.2143(3) 0.58146(17) 0.2038(3) 0.0433(9) Uani 1 1 d . . . . .
H21 H 0.242491 0.547488 0.198725 0.052 Uiso 1 1 calc R U . . .
Cl1 Cl 0.27958(7) 0.52899(5) 0.58349(8) 0.0493(3) Uani 1 1 d . . . . .
N1 N 0.3683(2) 0.59327(15) 0.4247(3) 0.0447(8) Uani 1 1 d . . . . .
N2 N 0.3047(2) 0.49960(15) 0.3794(2) 0.0405(7) Uani 1 1 d . . . . .
N3 N 0.1252(2) 0.50490(16) 0.3918(3) 0.0453(8) Uani 1 1 d . . . . .
N4 N 0.1948(2) 0.59712(14) 0.2902(3) 0.0418(7) Uani 1 1 d . . . . .
O1 O 0.1554(2) 0.62490(13) 0.4604(2) 0.0504(7) Uani 1 1 d . . . . .
O2 O 0.0812(2) 0.69996(14) 0.4022(3) 0.0561(8) Uani 1 1 d . . . . .
O3 O 0.1991(2) 0.69246(13) -0.0458(3) 0.0549(8) Uani 1 1 d . . . . .
O4 O 0.1482(3) 0.76351(14) 0.0654(3) 0.0579(8) Uani 1 1 d . . . . .
H4A H 0.205(6) 0.777(3) 0.058(5) 0.087 Uiso 1 1 d . U . . .
O5 O 0.0266(2) 0.70099(14) -0.0242(3) 0.0563(8) Uani 1 1 d . . . . .
H5 H -0.023(5) 0.708(3) 0.024(5) 0.084 Uiso 1 1 d . U . . .
P1 P 0.13315(8) 0.70708(5) 0.02321(9) 0.0491(3) Uani 1 1 d . . . . .
Ru1 Ru 0.23464(2) 0.55948(2) 0.41879(2) 0.04079(14) 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 0.0181 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'
Cl Cl 0.3639 0.7018 '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'
P P 0.2955 0.4335 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0106
0 -1 0 0.0026
-5 0 2 0.0716
5 0 -2 0.1016
-1 5 -4 0.0086
1 -1 5 0.0129
-1 -1 -5 0.0010
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 C1 H1 119.1 . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.9(5) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.2(5) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.5(5) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 124.4(4) . . ?
N1 C5 C4 120.6(4) . . ?
N1 C5 C6 115.0(3) . . ?
C7 C6 C5 128.0(4) . . ?
N2 C6 C5 112.4(4) . . ?
N2 C6 C7 119.5(4) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.2(4) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(4) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 C11 128.3(4) . . ?
N2 C10 C9 120.1(4) . . ?
N2 C10 C11 111.5(4) . . ?
C12 C11 C10 123.5(4) . . ?
N3 C11 C10 115.4(4) . . ?
N3 C11 C12 121.2(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(5) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.5 . . ?
C14 C13 C12 119.0(5) . . ?
C14 C13 H13 120.5 . . ?
C13 C14 H14 120.3 . . ?
C13 C14 C15 119.4(4) . . ?
C15 C14 H14 120.3 . . ?
C14 C15 H15 118.8 . . ?
N3 C15 C14 122.4(5) . . ?
N3 C15 H15 118.8 . . ?
O1 C16 C17 116.0(4) . . ?
O2 C16 C17 118.4(4) . . ?
O2 C16 O1 125.5(4) . . ?
C18 C17 C16 123.5(4) . . ?
N4 C17 C16 114.6(4) . . ?
N4 C17 C18 121.9(4) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.8(4) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 118.7(4) . . ?
C18 C19 P1 121.2(3) . . ?
C20 C19 P1 120.1(4) . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.2(4) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 119.0 . . ?
N4 C21 C20 122.0(4) . . ?
N4 C21 H21 119.0 . . ?
C1 N1 C5 119.1(4) . . ?
C1 N1 Ru1 127.5(3) . . ?
C5 N1 Ru1 113.2(3) . . ?
C6 N2 Ru1 119.1(3) . . ?
C10 N2 C6 121.4(4) . . ?
C10 N2 Ru1 119.0(3) . . ?
C11 N3 Ru1 113.1(3) . . ?
C15 N3 C11 118.0(4) . . ?
C15 N3 Ru1 129.0(3) . . ?
C17 N4 Ru1 115.2(3) . . ?
C21 N4 C17 118.2(4) . . ?
C21 N4 Ru1 126.2(3) . . ?
C16 O1 Ru1 114.9(3) . . ?
P1 O4 H4A 112(5) . . ?
P1 O5 H5 114(4) . . ?
O3 P1 C19 109.6(2) . . ?
O3 P1 O4 114.47(19) . . ?
O3 P1 O5 111.6(2) . . ?
O4 P1 C19 104.8(2) . . ?
O5 P1 C19 107.52(18) . . ?
O5 P1 O4 108.4(2) . . ?
N1 Ru1 Cl1 90.41(10) . . ?
N1 Ru1 O1 100.90(13) . . ?
N2 Ru1 Cl1 87.70(10) . . ?
N2 Ru1 N1 79.93(14) . . ?
N2 Ru1 N3 80.19(14) . . ?
N2 Ru1 N4 100.99(14) . . ?
N2 Ru1 O1 178.98(13) . . ?
N3 Ru1 Cl1 91.46(10) . . ?
N3 Ru1 N1 159.93(15) . . ?
N3 Ru1 O1 98.96(14) . . ?
N4 Ru1 Cl1 170.45(11) . . ?
N4 Ru1 N1 87.26(14) . . ?
N4 Ru1 N3 93.90(14) . . ?
N4 Ru1 O1 78.49(13) . . ?
O1 Ru1 Cl1 92.87(9) . . ?
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
C1 H1 0.9500 . ?
C1 C2 1.382(7) . ?
C1 N1 1.345(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.391(6) . ?
C5 C6 1.452(6) . ?
C5 N1 1.376(5) . ?
C6 C7 1.380(6) . ?
C6 N2 1.369(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.367(7) . ?
C10 C11 1.481(6) . ?
C10 N2 1.364(6) . ?
C11 C12 1.385(7) . ?
C11 N3 1.359(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.368(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.374(7) . ?
C15 H15 0.9500 . ?
C15 N3 1.356(5) . ?
C16 C17 1.495(6) . ?
C16 O1 1.265(5) . ?
C16 O2 1.253(5) . ?
C17 C18 1.377(6) . ?
C17 N4 1.365(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.373(7) . ?
C19 C20 1.388(6) . ?
C19 P1 1.815(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(6) . ?
C21 H21 0.9500 . ?
C21 N4 1.341(6) . ?
Cl1 Ru1 2.3970(11) . ?
N1 Ru1 2.052(3) . ?
N2 Ru1 1.931(4) . ?
N3 Ru1 2.048(4) . ?
N4 Ru1 2.017(4) . ?
O1 Ru1 2.124(3) . ?
O3 P1 1.494(3) . ?
O4 H4A 0.90(8) . ?
O4 P1 1.537(4) . ?
O5 H5 1.07(7) . ?
O5 P1 1.536(3) . ?
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
_geom_hbond_publ_flag
C2 H2 O4 0.95 2.60 3.248(6) 125.9 8_566 yes
C12 H12 O3 0.95 2.42 3.173(6) 136.3 6_566 yes
O4 H4A O3 0.90(8) 1.58(8) 2.473(5) 174(7) 7_565 yes
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
C1 C2 C3 C4 1.8(10) . . . . ?
C2 C1 N1 C5 1.7(8) . . . . ?
C2 C1 N1 Ru1 -172.6(4) . . . . ?
C2 C3 C4 C5 -0.4(9) . . . . ?
C3 C4 C5 C6 179.2(5) . . . . ?
C3 C4 C5 N1 -0.5(7) . . . . ?
C4 C5 C6 C7 8.3(7) . . . . ?
C4 C5 C6 N2 -173.1(4) . . . . ?
C4 C5 N1 C1 -0.1(7) . . . . ?
C4 C5 N1 Ru1 175.0(4) . . . . ?
C5 C6 C7 C8 179.0(4) . . . . ?
C5 C6 N2 C10 -177.7(4) . . . . ?
C5 C6 N2 Ru1 -5.5(5) . . . . ?
C6 C5 N1 C1 -179.9(4) . . . . ?
C6 C5 N1 Ru1 -4.8(5) . . . . ?
C6 C7 C8 C9 -1.6(7) . . . . ?
C7 C6 N2 C10 1.0(6) . . . . ?
C7 C6 N2 Ru1 173.2(3) . . . . ?
C7 C8 C9 C10 1.2(7) . . . . ?
C8 C9 C10 C11 179.8(4) . . . . ?
C8 C9 C10 N2 0.3(7) . . . . ?
C9 C10 C11 C12 1.3(7) . . . . ?
C9 C10 C11 N3 -179.6(4) . . . . ?
C9 C10 N2 C6 -1.5(6) . . . . ?
C9 C10 N2 Ru1 -173.6(3) . . . . ?
C10 C11 C12 C13 -178.2(4) . . . . ?
C10 C11 N3 C15 174.3(4) . . . . ?
C10 C11 N3 Ru1 -6.1(5) . . . . ?
C11 C10 N2 C6 179.0(4) . . . . ?
C11 C10 N2 Ru1 6.8(5) . . . . ?
C11 C12 C13 C14 2.6(7) . . . . ?
C12 C11 N3 C15 -6.6(6) . . . . ?
C12 C11 N3 Ru1 173.1(3) . . . . ?
C12 C13 C14 C15 -3.8(7) . . . . ?
C13 C14 C15 N3 -0.2(7) . . . . ?
C14 C15 N3 C11 5.4(7) . . . . ?
C14 C15 N3 Ru1 -174.2(4) . . . . ?
C16 C17 C18 C19 -178.9(4) . . . . ?
C16 C17 N4 C21 176.8(3) . . . . ?
C16 C17 N4 Ru1 -9.2(4) . . . . ?
C17 C16 O1 Ru1 2.4(5) . . . . ?
C17 C18 C19 C20 2.7(6) . . . . ?
C17 C18 C19 P1 -178.0(3) . . . . ?
C18 C17 N4 C21 -2.3(6) . . . . ?
C18 C17 N4 Ru1 171.7(3) . . . . ?
C18 C19 C20 C21 -3.3(6) . . . . ?
C18 C19 P1 O3 156.3(3) . . . . ?
C18 C19 P1 O4 33.0(4) . . . . ?
C18 C19 P1 O5 -82.2(4) . . . . ?
C19 C20 C21 N4 1.1(6) . . . . ?
C20 C19 P1 O3 -24.4(4) . . . . ?
C20 C19 P1 O4 -147.7(3) . . . . ?
C20 C19 P1 O5 97.1(4) . . . . ?
C20 C21 N4 C17 1.7(6) . . . . ?
C20 C21 N4 Ru1 -171.6(3) . . . . ?
N1 C1 C2 C3 -2.5(9) . . . . ?
N1 C5 C6 C7 -172.0(4) . . . . ?
N1 C5 C6 N2 6.6(5) . . . . ?
N2 C6 C7 C8 0.5(6) . . . . ?
N2 C10 C11 C12 -179.2(4) . . . . ?
N2 C10 C11 N3 0.0(5) . . . . ?
N3 C11 C12 C13 2.7(7) . . . . ?
N4 C17 C18 C19 0.1(6) . . . . ?
O1 C16 C17 C18 -176.6(4) . . . . ?
O1 C16 C17 N4 4.3(6) . . . . ?
O2 C16 C17 C18 4.9(7) . . . . ?
O2 C16 C17 N4 -174.1(4) . . . . ?
O2 C16 O1 Ru1 -179.3(4) . . . . ?
P1 C19 C20 C21 177.4(3) . . . . ?
