# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 2104829'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2021-10-22 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 N2 O4 Ru'
_chemical_formula_weight         395.41

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.8530(4)
_cell_length_b                   10.6283(6)
_cell_length_c                   21.8157(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1588.96(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.801
_cell_measurement_theta_max      36.981

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    1.006
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2762
_exptl_absorpt_correction_T_max  0.3447
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.0992 (selected reflections only, before parameter refinement)
 R(int) =  0.0494 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24410
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.867
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3472
_reflns_number_gt                3471
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0087P)²+0.9232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3472
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0141
_refine_ls_R_factor_gt           0.0141
_refine_ls_wR_factor_ref         0.0352
_refine_ls_wR_factor_gt          0.0352
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_restrained_S_all      1.157
_refine_ls_shift/su_max          0.001
_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_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 0.36025(2) 0.64321(2) 0.37472(2) 0.01062(5) Uani 1 1 d . . . . .
O1 O 0.5553(3) 0.76613(16) 0.33400(8) 0.0158(3) Uani 1 1 d . . . . .
O2 O 0.7228(3) 0.81327(17) 0.24954(9) 0.0225(4) Uani 1 1 d . . . . .
C1 C 0.6022(3) 0.7485(2) 0.27744(11) 0.0156(5) Uani 1 1 d . . . . .
C2 C 0.5035(4) 0.6405(2) 0.24376(10) 0.0168(4) Uani 1 1 d . . . . .
H2 H 0.6038 0.5748 0.2345 0.020 Uiso 1 1 calc R U . . .
N1 N 0.3440(3) 0.58136(18) 0.28217(8) 0.0129(4) Uani 1 1 d . . . . .
H1 H 0.3706 0.4889 0.2827 0.016 Uiso 1 1 calc R U . . .
C3 C 0.4072(4) 0.6810(3) 0.18334(12) 0.0261(6) Uani 1 1 d . . . . .
H3A H 0.3737 0.7716 0.1840 0.031 Uiso 1 1 calc R U . . .
H3B H 0.4940 0.6642 0.1480 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2233(4) 0.5997(3) 0.18028(12) 0.0235(5) Uani 1 1 d . . . . .
H4A H 0.1232 0.6378 0.1534 0.028 Uiso 1 1 calc R U . . .
H4B H 0.2532 0.5137 0.1656 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1579(4) 0.5990(2) 0.24698(11) 0.0205(5) Uani 1 1 d . . . . .
H5A H 0.0942 0.6795 0.2580 0.025 Uiso 1 1 calc R U . . .
H5B H 0.0659 0.5291 0.2549 0.025 Uiso 1 1 calc R U . . .
N2 N 0.5980(3) 0.52104(18) 0.38158(10) 0.0166(4) Uani 1 1 d . . . . .
O3 O 0.6561(3) 0.4838(2) 0.43261(9) 0.0316(5) Uani 1 1 d . . . . .
O4 O 0.6868(3) 0.48577(19) 0.33500(9) 0.0235(4) Uani 1 1 d . . . . .
C101 C 0.1847(3) 0.8035(2) 0.40997(11) 0.0173(5) Uani 1 1 d . . . . .
C102 C 0.3146(4) 0.7588(2) 0.45711(11) 0.0181(5) Uani 1 1 d . . . . .
H102 H 0.4222 0.8146 0.4720 0.022 Uiso 1 1 calc R U . . .
C103 C 0.3135(3) 0.6316(3) 0.47402(10) 0.0167(5) Uani 1 1 d . . . . .
H103 H 0.4228 0.5998 0.5001 0.020 Uiso 1 1 calc R U . . .
C104 C 0.1901(3) 0.5412(2) 0.44434(10) 0.0144(5) Uani 1 1 d . . . . .
C105 C 0.0648(3) 0.5862(2) 0.39810(11) 0.0147(4) Uani 1 1 d . . . . .
H105 H -0.0039 0.5243 0.3712 0.018 Uiso 1 1 calc R U . . .
C106 C 0.0573(3) 0.7179(2) 0.38256(11) 0.0155(5) Uani 1 1 d . . . . .
H106 H -0.0126 0.7435 0.3443 0.019 Uiso 1 1 calc R U . . .
C107 C 0.1984(4) 0.9379(2) 0.38868(13) 0.0249(6) Uani 1 1 d . . . . .
H10A H 0.1206 0.9487 0.3513 0.037 Uiso 1 1 calc R U . . .
H10B H 0.3349 0.9588 0.3800 0.037 Uiso 1 1 calc R U . . .
H10C H 0.1485 0.9939 0.4208 0.037 Uiso 1 1 calc R U . . .
C108 C 0.2038(4) 0.4034(2) 0.46235(11) 0.0174(5) Uani 1 1 d . . . . .
H108 H 0.3440 0.3836 0.4706 0.021 Uiso 1 1 calc R U . . .
C109 C 0.0897(5) 0.3837(3) 0.52199(12) 0.0272(6) Uani 1 1 d . . . . .
H10D H 0.1357 0.4434 0.5530 0.041 Uiso 1 1 calc R U . . .
H10E H 0.1100 0.2976 0.5367 0.041 Uiso 1 1 calc R U . . .
H10F H -0.0496 0.3975 0.5144 0.041 Uiso 1 1 calc R U . . .
C110 C 0.1313(5) 0.3140(2) 0.41278(11) 0.0228(5) Uani 1 1 d . . . . .
H11A H -0.0079 0.3288 0.4055 0.034 Uiso 1 1 calc R U . . .
H11B H 0.1510 0.2269 0.4261 0.034 Uiso 1 1 calc R U . . .
H11C H 0.2043 0.3289 0.3748 0.034 Uiso 1 1 calc R U . . .


_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 O1 2.0694(17) . ?
Ru1 N2 2.0888(18) . ?
Ru1 N1 2.1262(18) . ?
Ru1 C105 2.174(2) . ?
Ru1 C103 2.193(2) . ?
Ru1 C102 2.199(2) . ?
Ru1 C104 2.200(2) . ?
Ru1 C101 2.223(2) . ?
Ru1 C106 2.229(2) . ?
O1 C1 1.289(3) . ?
O2 C1 1.236(3) . ?
C1 C2 1.521(3) . ?
C2 N1 1.514(3) . ?
C2 C3 1.536(3) . ?
C2 H2 1.0000 . ?
N1 C5 1.501(3) . ?
N1 H1 1.0000 . ?
C3 C4 1.530(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.522(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
N2 O4 1.242(3) . ?
N2 O3 1.247(3) . ?
C101 C106 1.396(3) . ?
C101 C102 1.441(4) . ?
C101 C107 1.505(4) . ?
C102 C103 1.401(4) . ?
C102 H102 1.0000 . ?
C103 C104 1.434(3) . ?
C103 H103 1.0000 . ?
C104 C105 1.408(3) . ?
C104 C108 1.519(3) . ?
C105 C106 1.440(3) . ?
C105 H105 1.0000 . ?
C106 H106 1.0000 . ?
C107 H10A 0.9800 . ?
C107 H10B 0.9800 . ?
C107 H10C 0.9800 . ?
C108 C110 1.523(3) . ?
C108 C109 1.532(3) . ?
C108 H108 1.0000 . ?
C109 H10D 0.9800 . ?
C109 H10E 0.9800 . ?
C109 H10F 0.9800 . ?
C110 H11A 0.9800 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?

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
O1 Ru1 N2 85.38(7) . . ?
O1 Ru1 N1 79.70(7) . . ?
N2 Ru1 N1 85.22(8) . . ?
O1 Ru1 C105 151.41(8) . . ?
N2 Ru1 C105 122.45(8) . . ?
N1 Ru1 C105 95.06(9) . . ?
O1 Ru1 C103 123.63(8) . . ?
N2 Ru1 C103 90.47(9) . . ?
N1 Ru1 C103 155.91(9) . . ?
C105 Ru1 C103 67.45(9) . . ?
O1 Ru1 C102 95.17(8) . . ?
N2 Ru1 C102 113.55(9) . . ?
N1 Ru1 C102 160.26(8) . . ?
C105 Ru1 C102 80.28(9) . . ?
C103 Ru1 C102 37.19(10) . . ?
O1 Ru1 C104 161.73(7) . . ?
N2 Ru1 C104 93.30(8) . . ?
N1 Ru1 C104 118.39(8) . . ?
C105 Ru1 C104 37.56(9) . . ?
C103 Ru1 C104 38.11(9) . . ?
C102 Ru1 C104 68.63(9) . . ?
O1 Ru1 C101 90.81(8) . . ?
N2 Ru1 C101 150.90(9) . . ?
N1 Ru1 C101 122.49(8) . . ?
C105 Ru1 C101 68.18(9) . . ?
C103 Ru1 C101 67.81(9) . . ?
C102 Ru1 C101 38.03(9) . . ?
C104 Ru1 C101 81.50(9) . . ?
O1 Ru1 C106 114.19(8) . . ?
N2 Ru1 C106 160.43(8) . . ?
N1 Ru1 C106 97.71(9) . . ?
C105 Ru1 C106 38.16(8) . . ?
C103 Ru1 C106 78.94(9) . . ?
C102 Ru1 C106 66.80(9) . . ?
C104 Ru1 C106 68.22(9) . . ?
C101 Ru1 C106 36.54(9) . . ?
C1 O1 Ru1 118.71(15) . . ?
O2 C1 O1 123.9(2) . . ?
O2 C1 C2 118.7(2) . . ?
O1 C1 C2 117.5(2) . . ?
N1 C2 C1 111.52(18) . . ?
N1 C2 C3 106.3(2) . . ?
C1 C2 C3 113.2(2) . . ?
N1 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C3 C2 H2 108.5 . . ?
C5 N1 C2 106.17(18) . . ?
C5 N1 Ru1 119.45(15) . . ?
C2 N1 Ru1 111.08(14) . . ?
C5 N1 H1 106.5 . . ?
C2 N1 H1 106.5 . . ?
Ru1 N1 H1 106.5 . . ?
C4 C3 C2 103.5(2) . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.0 . . ?
C5 C4 C3 101.7(2) . . ?
C5 C4 H4A 111.4 . . ?
C3 C4 H4A 111.4 . . ?
C5 C4 H4B 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
N1 C5 C4 103.9(2) . . ?
N1 C5 H5A 111.0 . . ?
C4 C5 H5A 111.0 . . ?
N1 C5 H5B 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
O4 N2 O3 118.5(2) . . ?
O4 N2 Ru1 120.74(16) . . ?
O3 N2 Ru1 120.70(17) . . ?
C106 C101 C102 118.5(2) . . ?
C106 C101 C107 121.7(2) . . ?
C102 C101 C107 119.7(2) . . ?
C106 C101 Ru1 71.96(13) . . ?
C102 C101 Ru1 70.08(13) . . ?
C107 C101 Ru1 125.93(17) . . ?
C103 C102 C101 120.2(2) . . ?
C103 C102 Ru1 71.17(14) . . ?
C101 C102 Ru1 71.89(13) . . ?
C103 C102 H102 119.4 . . ?
C101 C102 H102 119.4 . . ?
Ru1 C102 H102 119.4 . . ?
C102 C103 C104 122.0(2) . . ?
C102 C103 Ru1 71.64(14) . . ?
C104 C103 Ru1 71.21(13) . . ?
C102 C103 H103 118.2 . . ?
C104 C103 H103 118.2 . . ?
Ru1 C103 H103 118.2 . . ?
C105 C104 C103 117.1(2) . . ?
C105 C104 C108 123.4(2) . . ?
C103 C104 C108 119.5(2) . . ?
C105 C104 Ru1 70.20(13) . . ?
C103 C104 Ru1 70.68(13) . . ?
C108 C104 Ru1 128.38(16) . . ?
C104 C105 C106 121.4(2) . . ?
C104 C105 Ru1 72.24(13) . . ?
C106 C105 Ru1 73.01(14) . . ?
C104 C105 H105 118.9 . . ?
C106 C105 H105 118.9 . . ?
Ru1 C105 H105 118.9 . . ?
C101 C106 C105 120.7(2) . . ?
C101 C106 Ru1 71.50(13) . . ?
C105 C106 Ru1 68.83(13) . . ?
C101 C106 H106 118.6 . . ?
C105 C106 H106 118.6 . . ?
Ru1 C106 H106 118.6 . . ?
C101 C107 H10A 109.5 . . ?
C101 C107 H10B 109.5 . . ?
H10A C107 H10B 109.5 . . ?
C101 C107 H10C 109.5 . . ?
H10A C107 H10C 109.5 . . ?
H10B C107 H10C 109.5 . . ?
C104 C108 C110 113.4(2) . . ?
C104 C108 C109 108.7(2) . . ?
C110 C108 C109 110.6(2) . . ?
C104 C108 H108 108.0 . . ?
C110 C108 H108 108.0 . . ?
C109 C108 H108 108.0 . . ?
C108 C109 H10D 109.5 . . ?
C108 C109 H10E 109.5 . . ?
H10D C109 H10E 109.5 . . ?
C108 C109 H10F 109.5 . . ?
H10D C109 H10F 109.5 . . ?
H10E C109 H10F 109.5 . . ?
C108 C110 H11A 109.5 . . ?
C108 C110 H11B 109.5 . . ?
H11A C110 H11B 109.5 . . ?
C108 C110 H11C 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?

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 O1 C1 O2 -177.08(18) . . . . ?
Ru1 O1 C1 C2 2.4(3) . . . . ?
O2 C1 C2 N1 -173.3(2) . . . . ?
O1 C1 C2 N1 7.2(3) . . . . ?
O2 C1 C2 C3 -53.4(3) . . . . ?
O1 C1 C2 C3 127.1(2) . . . . ?
C1 C2 N1 C5 118.7(2) . . . . ?
C3 C2 N1 C5 -5.2(2) . . . . ?
C1 C2 N1 Ru1 -12.7(2) . . . . ?
C3 C2 N1 Ru1 -136.51(17) . . . . ?
N1 C2 C3 C4 -21.1(3) . . . . ?
C1 C2 C3 C4 -143.9(2) . . . . ?
C2 C3 C4 C5 38.7(3) . . . . ?
C2 N1 C5 C4 29.7(2) . . . . ?
Ru1 N1 C5 C4 156.10(16) . . . . ?
C3 C4 C5 N1 -42.5(2) . . . . ?
C106 C101 C102 C103 0.9(3) . . . . ?
C107 C101 C102 C103 -175.1(2) . . . . ?
Ru1 C101 C102 C103 -54.3(2) . . . . ?
C106 C101 C102 Ru1 55.2(2) . . . . ?
C107 C101 C102 Ru1 -120.8(2) . . . . ?
C101 C102 C103 C104 2.1(4) . . . . ?
Ru1 C102 C103 C104 -52.5(2) . . . . ?
C101 C102 C103 Ru1 54.6(2) . . . . ?
C102 C103 C104 C105 -1.7(3) . . . . ?
Ru1 C103 C104 C105 -54.39(18) . . . . ?
C102 C103 C104 C108 176.6(2) . . . . ?
Ru1 C103 C104 C108 123.9(2) . . . . ?
C102 C103 C104 Ru1 52.7(2) . . . . ?
C103 C104 C105 C106 -1.7(3) . . . . ?
C108 C104 C105 C106 -179.9(2) . . . . ?
Ru1 C104 C105 C106 -56.3(2) . . . . ?
C103 C104 C105 Ru1 54.63(18) . . . . ?
C108 C104 C105 Ru1 -123.6(2) . . . . ?
C102 C101 C106 C105 -4.1(3) . . . . ?
C107 C101 C106 C105 171.7(2) . . . . ?
Ru1 C101 C106 C105 50.1(2) . . . . ?
C102 C101 C106 Ru1 -54.26(19) . . . . ?
C107 C101 C106 Ru1 121.6(2) . . . . ?
C104 C105 C106 C101 4.7(4) . . . . ?
Ru1 C105 C106 C101 -51.3(2) . . . . ?
C104 C105 C106 Ru1 56.0(2) . . . . ?
C105 C104 C108 C110 21.2(3) . . . . ?
C103 C104 C108 C110 -157.0(2) . . . . ?
Ru1 C104 C108 C110 -69.1(3) . . . . ?
C105 C104 C108 C109 -102.2(3) . . . . ?
C103 C104 C108 C109 79.6(3) . . . . ?
Ru1 C104 C108 C109 167.53(18) . . . . ?

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
N1 H1 O2 1.00 2.09 2.968(3) 144.7 3_645
C3 H3A O4 0.99 2.35 3.327(3) 168.6 3_655

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.047


####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 2104830'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2021-10-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT342_2b                  
;
PROBLEM: Low Bond Precision on C-C Bonds
RESPONSE: The crystal is twinned and this limits 
the precision of the C-C bonds. 
;
# end Validation Reply Form 
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 Br N O3 Ru'
_chemical_formula_weight         445.31

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   6.8687(15)
_cell_length_b                   23.288(5)
_cell_length_c                   10.082(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.108(9)
_cell_angle_gamma                90
_cell_volume                     1612.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9682
_cell_measurement_theta_min      2.207
_cell_measurement_theta_max      33.7715

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    3.459
_shelx_estimated_absorpt_T_min   0.559
_shelx_estimated_absorpt_T_max   0.702
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5070
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1655 (selected reflections only, before parameter refinement)
 R(int) =  0.0905 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10106
_diffrn_reflns_av_unetI/netI     0.1012
_diffrn_reflns_av_R_equivalents  0.0781
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.020
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5346
_reflns_number_gt                5084
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.948
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 4-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1251P)²+17.2487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Twinning involves inversion, so Flack parameter cannot be determined
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5346
_refine_ls_number_parameters     384
_refine_ls_number_restraints     472
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2044
_refine_ls_wR_factor_gt          0.1959
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.111
_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_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 0.8402(3) 0.54851(7) 0.8561(2) 0.0134(4) Uani 1 1 d . U . . .
Br1 Br 0.5690(4) 0.55341(11) 1.0213(3) 0.0210(6) Uani 1 1 d . . . . .
O1 O 0.701(2) 0.6147(8) 0.7475(18) 0.015(4) Uani 1 1 d . U . . .
O2 O 0.598(3) 0.7057(8) 0.761(2) 0.020(4) Uani 1 1 d . U . . .
O3 O 1.209(3) 0.7087(8) 1.095(2) 0.024(4) Uani 1 1 d D U . . .
H3 H 1.1345 0.6873 1.1382 0.036 Uiso 1 1 calc DR U . . .
N1 N 0.952(3) 0.6247(10) 0.954(2) 0.016(4) Uani 1 1 d . U . . .
H1 H 0.9684 0.6167 1.0507 0.019 Uiso 1 1 calc R U . . .
C1 C 0.696(4) 0.6647(11) 0.802(3) 0.016(4) Uani 1 1 d . U . . .
C2 C 0.805(4) 0.6746(12) 0.934(3) 0.019(4) Uani 1 1 d . U . . .
H2 H 0.7093 0.6739 1.0075 0.023 Uiso 1 1 calc R U . . .
C3 C 0.929(4) 0.7279(11) 0.947(3) 0.020(4) Uani 1 1 d . U . . .
H3A H 0.8946 0.7493 1.0285 0.024 Uiso 1 1 calc R U . . .
H3B H 0.9070 0.7534 0.8698 0.024 Uiso 1 1 calc R U . . .
C4 C 1.152(4) 0.7080(11) 0.956(2) 0.019(4) Uani 1 1 d D U . . .
H4 H 1.2374 0.7329 0.9009 0.023 Uiso 1 1 calc R U . . .
C5 C 1.137(4) 0.6477(11) 0.902(3) 0.019(4) Uani 1 1 d . U . . .
H5A H 1.1342 0.6479 0.8037 0.023 Uiso 1 1 calc R U . . .
H5B H 1.2489 0.6242 0.9332 0.023 Uiso 1 1 calc R U . . .
C11 C 0.951(4) 0.5134(11) 0.678(3) 0.016(4) Uani 1 1 d . U . . .
C12 C 1.114(4) 0.5208(11) 0.769(2) 0.012(4) Uani 1 1 d . U . . .
H12 H 1.2172 0.5496 0.7501 0.014 Uiso 1 1 calc R U . . .
C13 C 1.095(4) 0.4986(10) 0.900(3) 0.012(4) Uani 1 1 d . U . . .
H13 H 1.1874 0.5125 0.9713 0.015 Uiso 1 1 calc R U . . .
C14 C 0.939(4) 0.4633(11) 0.937(3) 0.012(4) Uani 1 1 d . U . . .
C15 C 0.782(4) 0.4570(12) 0.842(3) 0.013(4) Uani 1 1 d . U . . .
H15 H 0.6546 0.4426 0.8748 0.016 Uiso 1 1 calc R U . . .
C16 C 0.789(4) 0.4786(12) 0.708(3) 0.017(4) Uani 1 1 d . U . . .
H16 H 0.6698 0.4785 0.6497 0.020 Uiso 1 1 calc R U . . .
C17 C 0.954(4) 0.5411(12) 0.539(3) 0.027(6) Uani 1 1 d . U . . .
H17A H 1.0734 0.5639 0.5307 0.040 Uiso 1 1 calc R U . . .
H17B H 0.9514 0.5110 0.4714 0.040 Uiso 1 1 calc R U . . .
H17C H 0.8405 0.5660 0.5275 0.040 Uiso 1 1 calc R U . . .
C18 C 0.925(4) 0.4433(11) 1.075(3) 0.019(4) Uani 1 1 d . U . . .
H18 H 0.7828 0.4393 1.0916 0.023 Uiso 1 1 calc R U . . .
C19 C 1.006(5) 0.4785(13) 1.187(3) 0.023(6) Uani 1 1 d . U . . .
H19A H 0.9840 0.4586 1.2710 0.034 Uiso 1 1 calc R U . . .
H19B H 1.1462 0.4840 1.1755 0.034 Uiso 1 1 calc R U . . .
H19C H 0.9411 0.5160 1.1881 0.034 Uiso 1 1 calc R U . . .
C20 C 1.010(4) 0.3810(12) 1.081(3) 0.020(6) Uani 1 1 d . U . . .
H20A H 1.0029 0.3665 1.1721 0.030 Uiso 1 1 calc R U . . .
H20B H 0.9347 0.3560 1.0214 0.030 Uiso 1 1 calc R U . . .
H20C H 1.1465 0.3816 1.0539 0.030 Uiso 1 1 calc R U . . .
C51 C 0.161(4) 0.1903(11) 0.693(3) 0.019(4) Uani 1 1 d . U . . .
C52 C 0.309(4) 0.1702(10) 0.590(3) 0.014(4) Uani 1 1 d . U . . .
H52 H 0.2346 0.1509 0.5169 0.017 Uiso 1 1 calc R U . . .
C53 C 0.449(4) 0.1263(12) 0.648(3) 0.022(5) Uani 1 1 d . U . . .
H53A H 0.3928 0.0872 0.6455 0.026 Uiso 1 1 calc R U . . .
H53B H 0.4864 0.1359 0.7412 0.026 Uiso 1 1 calc R U . . .
C54 C 0.623(4) 0.1313(12) 0.557(3) 0.017(4) Uani 1 1 d . U . . .
H54 H 0.7416 0.1182 0.6075 0.020 Uiso 1 1 calc R U . . .
C55 C 0.638(4) 0.1969(11) 0.537(3) 0.018(4) Uani 1 1 d . U . . .
H55A H 0.7092 0.2153 0.6119 0.022 Uiso 1 1 calc R U . . .
H55B H 0.7054 0.2061 0.4534 0.022 Uiso 1 1 calc R U . . .
C61 C 0.468(4) 0.3357(12) 0.779(3) 0.020(4) Uani 1 1 d . U . . .
C62 C 0.622(4) 0.3254(12) 0.703(3) 0.017(4) Uani 1 1 d . U . . .
H62 H 0.7174 0.2951 0.7312 0.020 Uiso 1 1 calc R U . . .
C63 C 0.614(4) 0.3425(11) 0.559(3) 0.018(4) Uani 1 1 d . U . . .
H63 H 0.7072 0.3263 0.4938 0.021 Uiso 1 1 calc R U . . .
C64 C 0.450(5) 0.3767(12) 0.517(3) 0.021(4) Uani 1 1 d . U . . .
C65 C 0.313(4) 0.3908(13) 0.609(3) 0.021(5) Uani 1 1 d . U . . .
H65 H 0.1873 0.4071 0.5746 0.026 Uiso 1 1 calc R U . . .
C66 C 0.318(4) 0.3712(11) 0.741(3) 0.017(4) Uani 1 1 d . U . . .
H66 H 0.2007 0.3754 0.7976 0.021 Uiso 1 1 calc R U . . .
C67 C 0.481(4) 0.3144(12) 0.922(3) 0.022(6) Uani 1 1 d . U . . .
H67A H 0.3615 0.3243 0.9680 0.033 Uiso 1 1 calc R U . . .
H67B H 0.4984 0.2726 0.9225 0.033 Uiso 1 1 calc R U . . .
H67C H 0.5928 0.3325 0.9676 0.033 Uiso 1 1 calc R U . . .
C68 C 0.432(5) 0.3985(13) 0.372(3) 0.026(5) Uani 1 1 d . U . . .
H68 H 0.2901 0.4004 0.3476 0.031 Uiso 1 1 calc R U . . .
C69 C 0.531(5) 0.3579(14) 0.273(3) 0.029(7) Uani 1 1 d . U . . .
H69A H 0.4730 0.3196 0.2785 0.043 Uiso 1 1 calc R U . . .
H69B H 0.5133 0.3729 0.1827 0.043 Uiso 1 1 calc R U . . .
H69C H 0.6707 0.3555 0.2947 0.043 Uiso 1 1 calc R U . . .
C70 C 0.512(5) 0.4595(15) 0.371(4) 0.034(7) Uani 1 1 d . U . . .
H70A H 0.4431 0.4829 0.4361 0.051 Uiso 1 1 calc R U . . .
H70B H 0.6514 0.4587 0.3946 0.051 Uiso 1 1 calc R U . . .
H70C H 0.4940 0.4761 0.2827 0.051 Uiso 1 1 calc R U . . .
Ru2 Ru 0.3429(3) 0.29814(7) 0.6063(2) 0.0135(4) Uani 1 1 d . U . . .
Br2 Br 0.0660(4) 0.28836(10) 0.4320(3) 0.0211(6) Uani 1 1 d . . . . .
O4 O 0.177(3) 0.2448(7) 0.723(2) 0.021(4) Uani 1 1 d . U . . .
O5 O 0.061(3) 0.1564(7) 0.751(2) 0.016(4) Uani 1 1 d . U . . .
O6 O 0.606(3) 0.0986(8) 0.442(2) 0.031(5) Uani 1 1 d . U . . .
H6 H 0.5160 0.1120 0.3936 0.047 Uiso 1 1 calc DR U . . .
N2 N 0.425(3) 0.2165(9) 0.530(2) 0.009(4) Uani 1 1 d . U . . .
H2A H 0.3873 0.2169 0.4340 0.011 Uiso 1 1 calc R U . . .


_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 O1 2.108(18) . ?
Ru1 C11 2.13(3) . ?
Ru1 C13 2.14(2) . ?
Ru1 N1 2.16(2) . ?
Ru1 C15 2.17(3) . ?
Ru1 C12 2.18(2) . ?
Ru1 C16 2.23(3) . ?
Ru1 C14 2.24(3) . ?
Ru1 Br1 2.525(3) . ?
O1 C1 1.29(3) . ?
O2 C1 1.24(3) . ?
O3 C4 1.46(2) . ?
O3 H3 0.8400 . ?
N1 C5 1.49(4) . ?
N1 C2 1.55(3) . ?
N1 H1 1.0000 . ?
C1 C2 1.53(4) . ?
C2 C3 1.51(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.60(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.51(4) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 C16 1.42(4) . ?
C11 C12 1.44(4) . ?
C11 C17 1.54(4) . ?
C12 C13 1.43(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.41(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.43(4) . ?
C14 C18 1.47(4) . ?
C15 C16 1.44(4) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.50(4) . ?
C18 C20 1.56(4) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C51 O5 1.21(3) . ?
C51 O4 1.31(3) . ?
C51 C52 1.54(4) . ?
C52 N2 1.48(3) . ?
C52 C53 1.51(4) . ?
C52 H52 1.0000 . ?
C53 C54 1.52(4) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 O6 1.39(3) . ?
C54 C55 1.55(4) . ?
C54 H54 1.0000 . ?
C55 N2 1.53(4) . ?
C55 H55A 0.9900 . ?
C55 H55B 0.9900 . ?
C61 C62 1.35(4) . ?
C61 C66 1.37(4) . ?
C61 C67 1.52(4) . ?
C61 Ru2 2.12(3) . ?
C62 C63 1.50(4) . ?
C62 Ru2 2.23(3) . ?
C62 H62 1.0000 . ?
C63 C64 1.44(4) . ?
C63 Ru2 2.19(3) . ?
C63 H63 1.0000 . ?
C64 C65 1.37(4) . ?
C64 C68 1.55(4) . ?
C64 Ru2 2.17(3) . ?
C65 C66 1.41(4) . ?
C65 Ru2 2.17(3) . ?
C65 H65 1.0000 . ?
C66 Ru2 2.19(3) . ?
C66 H66 1.0000 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 0.9800 . ?
C68 C70 1.53(5) . ?
C68 C69 1.55(4) . ?
C68 H68 1.0000 . ?
C69 H69A 0.9800 . ?
C69 H69B 0.9800 . ?
C69 H69C 0.9800 . ?
C70 H70A 0.9800 . ?
C70 H70B 0.9800 . ?
C70 H70C 0.9800 . ?
Ru2 O4 2.07(2) . ?
Ru2 N2 2.13(2) . ?
Ru2 Br2 2.574(3) . ?
O6 H6 0.8400 . ?
N2 H2A 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
O1 Ru1 C11 90.6(9) . . ?
O1 Ru1 C13 150.0(8) . . ?
C11 Ru1 C13 70.2(10) . . ?
O1 Ru1 N1 77.9(8) . . ?
C11 Ru1 N1 124.8(10) . . ?
C13 Ru1 N1 94.0(9) . . ?
O1 Ru1 C15 127.1(9) . . ?
C11 Ru1 C15 68.7(10) . . ?
C13 Ru1 C15 68.2(9) . . ?
N1 Ru1 C15 153.8(10) . . ?
O1 Ru1 C12 113.1(8) . . ?
C11 Ru1 C12 39.0(10) . . ?
C13 Ru1 C12 38.5(9) . . ?
N1 Ru1 C12 97.2(9) . . ?
C15 Ru1 C12 80.9(10) . . ?
O1 Ru1 C16 97.0(9) . . ?
C11 Ru1 C16 37.9(10) . . ?
C13 Ru1 C16 82.0(10) . . ?
N1 Ru1 C16 162.4(10) . . ?
C15 Ru1 C16 38.2(10) . . ?
C12 Ru1 C16 69.1(10) . . ?
O1 Ru1 C14 164.8(9) . . ?
C11 Ru1 C14 81.7(10) . . ?
C13 Ru1 C14 37.3(9) . . ?
N1 Ru1 C14 117.2(9) . . ?
C15 Ru1 C14 37.8(10) . . ?
C12 Ru1 C14 68.2(9) . . ?
C16 Ru1 C14 68.9(10) . . ?
O1 Ru1 Br1 88.7(5) . . ?
C11 Ru1 Br1 148.8(8) . . ?
C13 Ru1 Br1 119.8(7) . . ?
N1 Ru1 Br1 85.5(6) . . ?
C15 Ru1 Br1 87.2(8) . . ?
C12 Ru1 Br1 158.1(7) . . ?
C16 Ru1 Br1 111.4(7) . . ?
C14 Ru1 Br1 91.2(7) . . ?
C1 O1 Ru1 117.1(16) . . ?
C4 O3 H3 109.5 . . ?
C5 N1 C2 104(2) . . ?
C5 N1 Ru1 115.7(17) . . ?
C2 N1 Ru1 109.6(17) . . ?
C5 N1 H1 109.1 . . ?
C2 N1 H1 109.1 . . ?
Ru1 N1 H1 109.1 . . ?
O2 C1 O1 125(3) . . ?
O2 C1 C2 115(2) . . ?
O1 C1 C2 119(2) . . ?
C3 C2 C1 118(2) . . ?
C3 C2 N1 104(2) . . ?
C1 C2 N1 108(2) . . ?
C3 C2 H2 109.0 . . ?
C1 C2 H2 109.0 . . ?
N1 C2 H2 109.0 . . ?
C2 C3 C4 108(2) . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O3 C4 C5 112(2) . . ?
O3 C4 C3 107(2) . . ?
C5 C4 C3 101(2) . . ?
O3 C4 H4 112.1 . . ?
C5 C4 H4 112.1 . . ?
C3 C4 H4 112.1 . . ?
N1 C5 C4 105(2) . . ?
N1 C5 H5A 110.7 . . ?
C4 C5 H5A 110.7 . . ?
N1 C5 H5B 110.7 . . ?
C4 C5 H5B 110.7 . . ?
H5A C5 H5B 108.8 . . ?
C16 C11 C12 122(2) . . ?
C16 C11 C17 117(3) . . ?
C12 C11 C17 120(2) . . ?
C16 C11 Ru1 75.1(16) . . ?
C12 C11 Ru1 72.6(15) . . ?
C17 C11 Ru1 128.0(19) . . ?
C13 C12 C11 118(2) . . ?
C13 C12 Ru1 69.2(14) . . ?
C11 C12 Ru1 68.3(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
Ru1 C12 H12 120.0 . . ?
C14 C13 C12 123(2) . . ?
C14 C13 Ru1 75.3(15) . . ?
C12 C13 Ru1 72.4(14) . . ?
C14 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
Ru1 C13 H13 118.5 . . ?
C13 C14 C15 117(2) . . ?
C13 C14 C18 120(3) . . ?
C15 C14 C18 122(3) . . ?
C13 C14 Ru1 67.4(14) . . ?
C15 C14 Ru1 68.4(15) . . ?
C18 C14 Ru1 126.9(19) . . ?
C14 C15 C16 124(3) . . ?
C14 C15 Ru1 73.8(15) . . ?
C16 C15 Ru1 73.1(16) . . ?
C14 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
Ru1 C15 H15 117.8 . . ?
C11 C16 C15 116(3) . . ?
C11 C16 Ru1 67.1(15) . . ?
C15 C16 Ru1 68.7(15) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
Ru1 C16 H16 120.9 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C19 121(3) . . ?
C14 C18 C20 108(2) . . ?
C19 C18 C20 110(2) . . ?
C14 C18 H18 105.8 . . ?
C19 C18 H18 105.8 . . ?
C20 C18 H18 105.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 C51 O4 124(3) . . ?
O5 C51 C52 121(2) . . ?
O4 C51 C52 114(2) . . ?
N2 C52 C53 108(2) . . ?
N2 C52 C51 115(2) . . ?
C53 C52 C51 112(2) . . ?
N2 C52 H52 107.3 . . ?
C53 C52 H52 107.3 . . ?
C51 C52 H52 107.3 . . ?
C52 C53 C54 102(2) . . ?
C52 C53 H53A 111.3 . . ?
C54 C53 H53A 111.3 . . ?
C52 C53 H53B 111.3 . . ?
C54 C53 H53B 111.3 . . ?
H53A C53 H53B 109.2 . . ?
O6 C54 C53 114(2) . . ?
O6 C54 C55 116(2) . . ?
C53 C54 C55 102(2) . . ?
O6 C54 H54 108.1 . . ?
C53 C54 H54 108.1 . . ?
C55 C54 H54 108.1 . . ?
N2 C55 C54 103(2) . . ?
N2 C55 H55A 111.1 . . ?
C54 C55 H55A 111.1 . . ?
N2 C55 H55B 111.1 . . ?
C54 C55 H55B 111.1 . . ?
H55A C55 H55B 109.1 . . ?
C62 C61 C66 123(3) . . ?
C62 C61 C67 117(3) . . ?
C66 C61 C67 120(3) . . ?
C62 C61 Ru2 76.3(16) . . ?
C66 C61 Ru2 74.0(17) . . ?
C67 C61 Ru2 131(2) . . ?
C61 C62 C63 120(2) . . ?
C61 C62 Ru2 67.7(17) . . ?
C63 C62 Ru2 68.8(14) . . ?
C61 C62 H62 118.5 . . ?
C63 C62 H62 118.5 . . ?
Ru2 C62 H62 118.5 . . ?
C64 C63 C62 116(2) . . ?
C64 C63 Ru2 70.1(16) . . ?
C62 C63 Ru2 71.5(14) . . ?
C64 C63 H63 121.5 . . ?
C62 C63 H63 121.5 . . ?
Ru2 C63 H63 121.5 . . ?
C65 C64 C63 118(3) . . ?
C65 C64 C68 121(3) . . ?
C63 C64 C68 121(3) . . ?
C65 C64 Ru2 71.3(17) . . ?
C63 C64 Ru2 71.4(15) . . ?
C68 C64 Ru2 130(2) . . ?
C64 C65 C66 124(3) . . ?
C64 C65 Ru2 71.8(17) . . ?
C66 C65 Ru2 71.8(17) . . ?
C64 C65 H65 117.0 . . ?
C66 C65 H65 117.0 . . ?
Ru2 C65 H65 117.0 . . ?
C61 C66 C65 118(3) . . ?
C61 C66 Ru2 68.9(16) . . ?
C65 C66 Ru2 70.5(16) . . ?
C61 C66 H66 120.4 . . ?
C65 C66 H66 120.4 . . ?
Ru2 C66 H66 120.4 . . ?
C61 C67 H67A 109.5 . . ?
C61 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
C61 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 109.5 . . ?
C70 C68 C69 114(3) . . ?
C70 C68 C64 107(3) . . ?
C69 C68 C64 112(3) . . ?
C70 C68 H68 107.9 . . ?
C69 C68 H68 107.9 . . ?
C64 C68 H68 107.9 . . ?
C68 C69 H69A 109.5 . . ?
C68 C69 H69B 109.5 . . ?
H69A C69 H69B 109.5 . . ?
C68 C69 H69C 109.5 . . ?
H69A C69 H69C 109.5 . . ?
H69B C69 H69C 109.5 . . ?
C68 C70 H70A 109.5 . . ?
C68 C70 H70B 109.5 . . ?
H70A C70 H70B 109.5 . . ?
C68 C70 H70C 109.5 . . ?
H70A C70 H70C 109.5 . . ?
H70B C70 H70C 109.5 . . ?
O4 Ru2 C61 89.9(10) . . ?
O4 Ru2 N2 79.7(8) . . ?
C61 Ru2 N2 124.0(10) . . ?
O4 Ru2 C65 122.5(9) . . ?
C61 Ru2 C65 67.4(11) . . ?
N2 Ru2 C65 156.8(10) . . ?
O4 Ru2 C64 159.3(9) . . ?
C61 Ru2 C64 81.8(11) . . ?
N2 Ru2 C64 120.6(9) . . ?
C65 Ru2 C64 36.9(11) . . ?
O4 Ru2 C66 93.6(9) . . ?
C61 Ru2 C66 37.1(11) . . ?
N2 Ru2 C66 160.5(9) . . ?
C65 Ru2 C66 37.7(11) . . ?
C64 Ru2 C66 68.5(10) . . ?
O4 Ru2 C63 152.5(10) . . ?
C61 Ru2 C63 69.6(11) . . ?
N2 Ru2 C63 96.3(9) . . ?
C65 Ru2 C63 67.3(11) . . ?
C64 Ru2 C63 38.5(11) . . ?
C66 Ru2 C63 81.1(10) . . ?
O4 Ru2 C62 113.8(9) . . ?
C61 Ru2 C62 35.9(10) . . ?
N2 Ru2 C62 100.3(9) . . ?
C65 Ru2 C62 77.9(11) . . ?
C64 Ru2 C62 69.2(11) . . ?
C66 Ru2 C62 65.5(10) . . ?
C63 Ru2 C62 39.7(10) . . ?
O4 Ru2 Br2 85.8(6) . . ?
C61 Ru2 Br2 151.8(8) . . ?
N2 Ru2 Br2 82.7(6) . . ?
C65 Ru2 Br2 91.6(8) . . ?
C64 Ru2 Br2 92.5(8) . . ?
C66 Ru2 Br2 115.3(8) . . ?
C63 Ru2 Br2 120.9(8) . . ?
C62 Ru2 Br2 160.4(7) . . ?
C51 O4 Ru2 119.5(18) . . ?
C54 O6 H6 109.5 . . ?
C52 N2 C55 107(2) . . ?
C52 N2 Ru2 110.8(16) . . ?
C55 N2 Ru2 120.6(16) . . ?
C52 N2 H2A 105.9 . . ?
C55 N2 H2A 105.9 . . ?
Ru2 N2 H2A 105.9 . . ?

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 O1 C1 O2 -169(2) . . . . ?
Ru1 O1 C1 C2 5(3) . . . . ?
O2 C1 C2 C3 -51(3) . . . . ?
O1 C1 C2 C3 134(3) . . . . ?
O2 C1 C2 N1 -168(2) . . . . ?
O1 C1 C2 N1 17(3) . . . . ?
C5 N1 C2 C3 -31(3) . . . . ?
Ru1 N1 C2 C3 -155.0(18) . . . . ?
C5 N1 C2 C1 95(2) . . . . ?
Ru1 N1 C2 C1 -29(2) . . . . ?
C1 C2 C3 C4 -112(3) . . . . ?
N1 C2 C3 C4 7(3) . . . . ?
C2 C3 C4 O3 -99(2) . . . . ?
C2 C3 C4 C5 18(3) . . . . ?
C2 N1 C5 C4 44(3) . . . . ?
Ru1 N1 C5 C4 163.8(16) . . . . ?
O3 C4 C5 N1 76(3) . . . . ?
C3 C4 C5 N1 -37(2) . . . . ?
C16 C11 C12 C13 -9(4) . . . . ?
C17 C11 C12 C13 174(2) . . . . ?
Ru1 C11 C12 C13 50(2) . . . . ?
C16 C11 C12 Ru1 -59(2) . . . . ?
C17 C11 C12 Ru1 124(2) . . . . ?
C11 C12 C13 C14 9(4) . . . . ?
Ru1 C12 C13 C14 59(2) . . . . ?
C11 C12 C13 Ru1 -50(2) . . . . ?
C12 C13 C14 C15 -9(4) . . . . ?
Ru1 C13 C14 C15 49(2) . . . . ?
C12 C13 C14 C18 -178(2) . . . . ?
Ru1 C13 C14 C18 -121(2) . . . . ?
C12 C13 C14 Ru1 -57(2) . . . . ?
C13 C14 C15 C16 8(4) . . . . ?
C18 C14 C15 C16 177(2) . . . . ?
Ru1 C14 C15 C16 56(2) . . . . ?
C13 C14 C15 Ru1 -48(2) . . . . ?
C18 C14 C15 Ru1 121(3) . . . . ?
C12 C11 C16 C15 8(4) . . . . ?
C17 C11 C16 C15 -175(2) . . . . ?
Ru1 C11 C16 C15 -50(2) . . . . ?
C12 C11 C16 Ru1 58(2) . . . . ?
C17 C11 C16 Ru1 -125(2) . . . . ?
C14 C15 C16 C11 -8(4) . . . . ?
Ru1 C15 C16 C11 49(2) . . . . ?
C14 C15 C16 Ru1 -57(2) . . . . ?
C13 C14 C18 C19 30(4) . . . . ?
C15 C14 C18 C19 -139(3) . . . . ?
Ru1 C14 C18 C19 -53(4) . . . . ?
C13 C14 C18 C20 -98(3) . . . . ?
C15 C14 C18 C20 93(3) . . . . ?
Ru1 C14 C18 C20 179.2(19) . . . . ?
O5 C51 C52 N2 -178(2) . . . . ?
O4 C51 C52 N2 -8(3) . . . . ?
O5 C51 C52 C53 -55(4) . . . . ?
O4 C51 C52 C53 116(3) . . . . ?
N2 C52 C53 C54 -30(3) . . . . ?
C51 C52 C53 C54 -158(2) . . . . ?
C52 C53 C54 O6 -85(3) . . . . ?
C52 C53 C54 C55 41(3) . . . . ?
O6 C54 C55 N2 88(3) . . . . ?
C53 C54 C55 N2 -37(2) . . . . ?
C66 C61 C62 C63 -13(4) . . . . ?
C67 C61 C62 C63 177(2) . . . . ?
Ru2 C61 C62 C63 47(2) . . . . ?
C66 C61 C62 Ru2 -60(3) . . . . ?
C67 C61 C62 Ru2 130(3) . . . . ?
C61 C62 C63 C64 9(4) . . . . ?
Ru2 C62 C63 C64 55(2) . . . . ?
C61 C62 C63 Ru2 -47(2) . . . . ?
C62 C63 C64 C65 -1(4) . . . . ?
Ru2 C63 C64 C65 55(2) . . . . ?
C62 C63 C64 C68 178(3) . . . . ?
Ru2 C63 C64 C68 -126(3) . . . . ?
C62 C63 C64 Ru2 -56(2) . . . . ?
C63 C64 C65 C66 -4(4) . . . . ?
C68 C64 C65 C66 178(3) . . . . ?
Ru2 C64 C65 C66 52(3) . . . . ?
C63 C64 C65 Ru2 -55(2) . . . . ?
C68 C64 C65 Ru2 126(3) . . . . ?
C62 C61 C66 C65 9(4) . . . . ?
C67 C61 C66 C65 179(3) . . . . ?
Ru2 C61 C66 C65 -53(2) . . . . ?
C62 C61 C66 Ru2 62(3) . . . . ?
C67 C61 C66 Ru2 -129(3) . . . . ?
C64 C65 C66 C61 0(4) . . . . ?
Ru2 C65 C66 C61 52(2) . . . . ?
C64 C65 C66 Ru2 -52(3) . . . . ?
C65 C64 C68 C70 82(4) . . . . ?
C63 C64 C68 C70 -96(3) . . . . ?
Ru2 C64 C68 C70 173(2) . . . . ?
C65 C64 C68 C69 -153(3) . . . . ?
C63 C64 C68 C69 29(4) . . . . ?
Ru2 C64 C68 C69 -62(4) . . . . ?
O5 C51 O4 Ru2 -177(2) . . . . ?
C52 C51 O4 Ru2 13(3) . . . . ?
C53 C52 N2 C55 7(3) . . . . ?
C51 C52 N2 C55 132(2) . . . . ?
C53 C52 N2 Ru2 -126.2(19) . . . . ?
C51 C52 N2 Ru2 -1(3) . . . . ?
C54 C55 N2 C52 19(3) . . . . ?
C54 C55 N2 Ru2 146.4(16) . . . . ?

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
O3 H3 O5 0.84 1.90 2.72(2) 165.8 2_657
N1 H1 O5 1.00 2.21 3.07(3) 142.6 2_657
C3 H3A O4 0.99 2.56 3.44(4) 147.1 2_657
C5 H5B Br1 0.99 2.87 3.86(3) 178.5 1_655
C53 H53B Br1 0.99 3.10 3.74(3) 123.9 2_647
O6 H6 O1 0.84 2.04 2.84(3) 159.4 2_646
N2 H2A O2 1.00 1.98 2.95(3) 160.4 2_646

_refine_diff_density_max         2.825
_refine_diff_density_min         -2.798
_refine_diff_density_rms         0.268


####################################################################### 
# 
# 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_2c
_database_code_depnum_ccdc_archive 'CCDC 2104831'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2021-10-22 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 N4 O3 Ru'
_chemical_formula_weight         407.43

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.1174(3)
_cell_length_b                   9.9265(4)
_cell_length_c                   23.0044(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1625.28(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9368
_cell_measurement_theta_min      3.357
_cell_measurement_theta_max      35.7825

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.985
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.908
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6216
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1570 (selected reflections only, before parameter refinement)
 R(int) =  0.0563 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33705
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.770
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3539
_reflns_number_gt                3457
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0175P)²+0.1444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1422 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(7)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3539
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0160
_refine_ls_R_factor_gt           0.0150
_refine_ls_wR_factor_ref         0.0374
_refine_ls_wR_factor_gt          0.0372
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_refine_ls_shift/su_max          0.003
_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_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 0.55643(3) 0.65152(2) 0.63215(2) 0.00897(5) Uani 1 1 d . . . . .
N1 N 0.6788(3) 0.5555(2) 0.70547(9) 0.0112(4) Uani 1 1 d . . . . .
H1 H 0.6458 0.4580 0.7016 0.013 Uiso 1 1 calc R U . . .
N2 N 0.3339(3) 0.5233(2) 0.65791(10) 0.0200(5) Uani 1 1 d . . . . .
N3 N 0.2430(3) 0.46595(19) 0.62425(10) 0.0149(4) Uani 1 1 d . . . . .
N4 N 0.1442(3) 0.4054(2) 0.59220(11) 0.0256(5) Uani 1 1 d . . . . .
O1 O 0.4497(3) 0.77091(15) 0.69905(7) 0.0154(3) Uani 1 1 d . . . . .
O2 O 0.3706(3) 0.76809(18) 0.79245(9) 0.0273(5) Uani 1 1 d . . . . .
O3 O 0.9058(3) 0.4205(2) 0.80489(11) 0.0351(6) Uani 1 1 d . . . . .
H3 H 0.7990 0.3869 0.7993 0.053 Uiso 1 1 calc R U . . .
C1 C 0.4564(4) 0.7216(2) 0.75068(11) 0.0166(5) Uani 1 1 d . . . . .
C2 C 0.5856(4) 0.6020(2) 0.76047(10) 0.0144(5) Uani 1 1 d . . . . .
H2 H 0.5119 0.5259 0.7776 0.017 Uiso 1 1 calc R U . . .
C3 C 0.7469(5) 0.6396(3) 0.80193(13) 0.0333(7) Uani 1 1 d . . . . .
H3A H 0.7771 0.7367 0.7990 0.040 Uiso 1 1 calc R U . . .
H3B H 0.7137 0.6182 0.8427 0.040 Uiso 1 1 calc R U . . .
C4 C 0.9107(4) 0.5540(3) 0.78148(13) 0.0251(6) Uani 1 1 d . . . . .
H4 H 1.0316 0.5986 0.7925 0.030 Uiso 1 1 calc R U . . .
C5 C 0.8863(4) 0.5588(4) 0.71606(13) 0.0279(7) Uani 1 1 d . . . . .
H5A H 0.9418 0.6423 0.7000 0.033 Uiso 1 1 calc R U . . .
H5B H 0.9480 0.4804 0.6976 0.033 Uiso 1 1 calc R U . . .
C11 C 0.6676(4) 0.8313(2) 0.58966(10) 0.0151(5) Uani 1 1 d . . . . .
C12 C 0.4919(4) 0.7958(2) 0.56367(11) 0.0166(6) Uani 1 1 d . . . . .
H12 H 0.3819 0.8575 0.5686 0.020 Uiso 1 1 calc R U . . .
C13 C 0.4618(4) 0.6646(2) 0.54230(10) 0.0159(5) Uani 1 1 d . . . . .
H13 H 0.3306 0.6361 0.5327 0.019 Uiso 1 1 calc R U . . .
C14 C 0.6051(4) 0.5639(2) 0.54599(11) 0.0137(5) Uani 1 1 d . . . . .
C15 C 0.7777(4) 0.6003(3) 0.57171(11) 0.0149(5) Uani 1 1 d . . . . .
H15 H 0.8687 0.5276 0.5824 0.018 Uiso 1 1 calc R U . . .
C16 C 0.8099(4) 0.7338(2) 0.59258(11) 0.0147(5) Uani 1 1 d . . . . .
H16 H 0.9219 0.7514 0.6177 0.018 Uiso 1 1 calc R U . . .
C17 C 0.6956(4) 0.9691(2) 0.61526(11) 0.0204(6) Uani 1 1 d . . . . .
H17A H 0.7748 0.9623 0.6500 0.031 Uiso 1 1 calc R U . . .
H17B H 0.5735 1.0074 0.6259 0.031 Uiso 1 1 calc R U . . .
H17C H 0.7569 1.0274 0.5866 0.031 Uiso 1 1 calc R U . . .
C18 C 0.5691(4) 0.4249(2) 0.52094(10) 0.0153(5) Uani 1 1 d . . . . .
H18 H 0.4299 0.4128 0.5180 0.018 Uiso 1 1 calc R U . . .
C19 C 0.6495(5) 0.4198(3) 0.45914(11) 0.0222(6) Uani 1 1 d . . . . .
H19A H 0.5994 0.4952 0.4364 0.033 Uiso 1 1 calc R U . . .
H19B H 0.6135 0.3346 0.4407 0.033 Uiso 1 1 calc R U . . .
H19C H 0.7867 0.4262 0.4608 0.033 Uiso 1 1 calc R U . . .
C20 C 0.6452(5) 0.3100(2) 0.55745(13) 0.0242(6) Uani 1 1 d . . . . .
H20A H 0.7822 0.3178 0.5603 0.036 Uiso 1 1 calc R U . . .
H20B H 0.6127 0.2239 0.5392 0.036 Uiso 1 1 calc R U . . .
H20C H 0.5901 0.3140 0.5964 0.036 Uiso 1 1 calc R U . . .


_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 O1 2.0857(17) . ?
Ru1 N2 2.116(2) . ?
Ru1 N1 2.124(2) . ?
Ru1 C15 2.162(3) . ?
Ru1 C13 2.178(2) . ?
Ru1 C12 2.178(2) . ?
Ru1 C16 2.180(3) . ?
Ru1 C11 2.183(2) . ?
Ru1 C14 2.192(2) . ?
N1 C5 1.497(3) . ?
N1 C2 1.501(3) . ?
N1 H1 1.0000 . ?
N2 N3 1.158(3) . ?
N3 N4 1.183(3) . ?
O1 C1 1.286(3) . ?
O2 C1 1.229(3) . ?
O3 C4 1.431(3) . ?
O3 H3 0.8400 . ?
C1 C2 1.519(3) . ?
C2 C3 1.538(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.517(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(4) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 C16 1.403(4) . ?
C11 C12 1.430(4) . ?
C11 C17 1.502(3) . ?
C12 C13 1.408(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.431(4) . ?
C13 H13 1.0000 . ?
C14 C15 1.411(4) . ?
C14 C18 1.518(3) . ?
C15 C16 1.429(3) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.516(3) . ?
C18 C19 1.533(3) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O1 Ru1 N2 82.10(8) . . ?
O1 Ru1 N1 79.54(7) . . ?
N2 Ru1 N1 79.33(9) . . ?
O1 Ru1 C15 150.89(9) . . ?
N2 Ru1 C15 125.72(9) . . ?
N1 Ru1 C15 96.11(9) . . ?
O1 Ru1 C13 123.61(8) . . ?
N2 Ru1 C13 94.02(10) . . ?
N1 Ru1 C13 155.14(8) . . ?
C15 Ru1 C13 68.23(10) . . ?
O1 Ru1 C12 94.77(8) . . ?
N2 Ru1 C12 116.11(10) . . ?
N1 Ru1 C12 162.90(9) . . ?
C15 Ru1 C12 80.98(10) . . ?
C13 Ru1 C12 37.73(9) . . ?
O1 Ru1 C16 113.37(9) . . ?
N2 Ru1 C16 164.10(9) . . ?
N1 Ru1 C16 99.23(9) . . ?
C15 Ru1 C16 38.42(9) . . ?
C13 Ru1 C16 80.64(10) . . ?
C12 Ru1 C16 68.04(10) . . ?
O1 Ru1 C11 89.88(8) . . ?
N2 Ru1 C11 152.63(10) . . ?
N1 Ru1 C11 125.01(9) . . ?
C15 Ru1 C11 68.92(10) . . ?
C13 Ru1 C11 68.80(9) . . ?
C12 Ru1 C11 38.28(9) . . ?
C16 Ru1 C11 37.51(9) . . ?
O1 Ru1 C14 161.84(8) . . ?
N2 Ru1 C14 97.64(9) . . ?
N1 Ru1 C14 118.38(9) . . ?
C15 Ru1 C14 37.80(10) . . ?
C13 Ru1 C14 38.23(9) . . ?
C12 Ru1 C14 68.91(9) . . ?
C16 Ru1 C14 68.91(9) . . ?
C11 Ru1 C14 82.07(9) . . ?
C5 N1 C2 107.0(2) . . ?
C5 N1 Ru1 121.60(17) . . ?
C2 N1 Ru1 110.51(15) . . ?
C5 N1 H1 105.5 . . ?
C2 N1 H1 105.5 . . ?
Ru1 N1 H1 105.5 . . ?
N3 N2 Ru1 121.76(19) . . ?
N2 N3 N4 176.5(3) . . ?
C1 O1 Ru1 116.86(15) . . ?
C4 O3 H3 109.5 . . ?
O2 C1 O1 124.1(2) . . ?
O2 C1 C2 118.6(2) . . ?
O1 C1 C2 117.2(2) . . ?
N1 C2 C1 112.49(19) . . ?
N1 C2 C3 105.5(2) . . ?
C1 C2 C3 110.7(2) . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C4 C3 C2 104.2(2) . . ?
C4 C3 H3A 110.9 . . ?
C2 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
O3 C4 C5 113.6(3) . . ?
O3 C4 C3 112.5(3) . . ?
C5 C4 C3 101.7(2) . . ?
O3 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
N1 C5 C4 105.9(2) . . ?
N1 C5 H5A 110.6 . . ?
C4 C5 H5A 110.6 . . ?
N1 C5 H5B 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C16 C11 C12 118.8(2) . . ?
C16 C11 C17 120.9(2) . . ?
C12 C11 C17 120.3(2) . . ?
C16 C11 Ru1 71.11(14) . . ?
C12 C11 Ru1 70.67(14) . . ?
C17 C11 Ru1 128.08(17) . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 Ru1 71.12(13) . . ?
C11 C12 Ru1 71.05(14) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
Ru1 C12 H12 119.1 . . ?
C12 C13 C14 121.1(2) . . ?
C12 C13 Ru1 71.16(13) . . ?
C14 C13 Ru1 71.42(14) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 H13 118.7 . . ?
Ru1 C13 H13 118.7 . . ?
C15 C14 C13 117.9(2) . . ?
C15 C14 C18 122.6(2) . . ?
C13 C14 C18 119.5(2) . . ?
C15 C14 Ru1 69.94(14) . . ?
C13 C14 Ru1 70.36(13) . . ?
C18 C14 Ru1 132.64(17) . . ?
C14 C15 C16 121.2(2) . . ?
C14 C15 Ru1 72.26(14) . . ?
C16 C15 Ru1 71.48(15) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 H15 118.9 . . ?
Ru1 C15 H15 118.9 . . ?
C11 C16 C15 120.6(2) . . ?
C11 C16 Ru1 71.39(15) . . ?
C15 C16 Ru1 70.11(15) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
Ru1 C16 H16 118.9 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C14 114.4(2) . . ?
C20 C18 C19 110.8(2) . . ?
C14 C18 C19 108.6(2) . . ?
C20 C18 H18 107.6 . . ?
C14 C18 H18 107.6 . . ?
C19 C18 H18 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 O1 C1 O2 -166.5(2) . . . . ?
Ru1 O1 C1 C2 16.1(3) . . . . ?
C5 N1 C2 C1 123.9(2) . . . . ?
Ru1 N1 C2 C1 -10.5(2) . . . . ?
C5 N1 C2 C3 3.1(3) . . . . ?
Ru1 N1 C2 C3 -131.31(19) . . . . ?
O2 C1 C2 N1 179.3(2) . . . . ?
O1 C1 C2 N1 -3.2(3) . . . . ?
O2 C1 C2 C3 -62.9(3) . . . . ?
O1 C1 C2 C3 114.6(3) . . . . ?
N1 C2 C3 C4 -26.2(3) . . . . ?
C1 C2 C3 C4 -148.1(2) . . . . ?
C2 C3 C4 O3 -83.4(3) . . . . ?
C2 C3 C4 C5 38.5(3) . . . . ?
C2 N1 C5 C4 21.3(3) . . . . ?
Ru1 N1 C5 C4 149.52(17) . . . . ?
O3 C4 C5 N1 84.0(3) . . . . ?
C3 C4 C5 N1 -37.1(3) . . . . ?
C16 C11 C12 C13 1.0(4) . . . . ?
C17 C11 C12 C13 -176.7(2) . . . . ?
Ru1 C11 C12 C13 -53.2(2) . . . . ?
C16 C11 C12 Ru1 54.2(2) . . . . ?
C17 C11 C12 Ru1 -123.5(2) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
Ru1 C12 C13 C14 -53.2(2) . . . . ?
C11 C12 C13 Ru1 53.2(2) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
Ru1 C13 C14 C15 -53.1(2) . . . . ?
C12 C13 C14 C18 -178.3(2) . . . . ?
Ru1 C13 C14 C18 128.6(2) . . . . ?
C12 C13 C14 Ru1 53.1(2) . . . . ?
C13 C14 C15 C16 -1.0(3) . . . . ?
C18 C14 C15 C16 177.2(2) . . . . ?
Ru1 C14 C15 C16 -54.3(2) . . . . ?
C13 C14 C15 Ru1 53.29(19) . . . . ?
C18 C14 C15 Ru1 -128.5(2) . . . . ?
C12 C11 C16 C15 -2.0(4) . . . . ?
C17 C11 C16 C15 175.7(2) . . . . ?
Ru1 C11 C16 C15 52.0(2) . . . . ?
C12 C11 C16 Ru1 -54.0(2) . . . . ?
C17 C11 C16 Ru1 123.7(2) . . . . ?
C14 C15 C16 C11 2.1(4) . . . . ?
Ru1 C15 C16 C11 -52.6(2) . . . . ?
C14 C15 C16 Ru1 54.6(2) . . . . ?
C15 C14 C18 C20 41.5(3) . . . . ?
C13 C14 C18 C20 -140.3(3) . . . . ?
Ru1 C14 C18 C20 -50.5(4) . . . . ?
C15 C14 C18 C19 -82.8(3) . . . . ?
C13 C14 C18 C19 95.3(3) . . . . ?
Ru1 C14 C18 C19 -174.9(2) . . . . ?

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
N1 H1 O2 1.00 1.89 2.875(3) 166.3 3_646
O3 H3 O1 0.84 2.11 2.935(3) 166.6 3_646
C2 H2 O1 1.00 2.60 3.425(3) 139.5 3_646
C5 H5B N3 0.99 2.70 3.429(4) 131.0 1_655

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.058


####################################################################### 
# 
# 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_2d
_database_code_depnum_ccdc_archive 'CCDC 2104832'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2021-10-22 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H22 N2 O3 Ru S'
_chemical_formula_weight         423.48

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   5.9679(9)
_cell_length_b                   9.9595(15)
_cell_length_c                   14.192(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.801(5)
_cell_angle_gamma                90
_cell_volume                     843.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7826
_cell_measurement_theta_min      2.4985
_cell_measurement_theta_max      29.4365

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.069
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.910
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.4245
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1559 (selected reflections only, before parameter refinement)
 R(int) =  0.08923 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13243
_diffrn_reflns_av_unetI/netI     0.0946
_diffrn_reflns_av_R_equivalents  0.1494
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.498
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2953
_reflns_number_gt                2569
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0331P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2953
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_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_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 0.76988(10) 0.49940(10) 0.75216(4) 0.01563(19) Uani 1 1 d . . . . .
N1 N 0.6350(12) 0.6111(7) 0.6352(4) 0.0148(16) Uani 1 1 d . . . . .
H1 H 0.5119 0.5558 0.6066 0.018 Uiso 1 1 calc R U . . .
O1 O 1.0255(9) 0.4744(6) 0.6554(3) 0.0182(17) Uani 1 1 d . . . . .
O2 O 1.1964(10) 0.5826(6) 0.5401(4) 0.0202(14) Uani 1 1 d . . . . .
O3 O 0.4441(11) 0.8154(7) 0.4949(4) 0.0246(16) Uani 1 1 d . . . . .
H3 H 0.3533 0.7535 0.5068 0.037 Uiso 1 1 calc R U . . .
C1 C 1.0272(15) 0.5585(9) 0.5871(6) 0.0168(19) Uani 1 1 d . . . . .
C2 C 0.8088(14) 0.6294(9) 0.5612(6) 0.0147(19) Uani 1 1 d . . . . .
H2 H 0.7499 0.5893 0.5012 0.018 Uiso 1 1 calc R U . . .
C3 C 0.8260(15) 0.7807(9) 0.5476(6) 0.020(2) Uani 1 1 d . . . . .
H3A H 0.9423 0.8196 0.5898 0.024 Uiso 1 1 calc R U . . .
H3B H 0.8622 0.8030 0.4815 0.024 Uiso 1 1 calc R U . . .
C4 C 0.5970(16) 0.8315(9) 0.5724(6) 0.023(2) Uani 1 1 d . . . . .
H4 H 0.6054 0.9281 0.5914 0.027 Uiso 1 1 calc R U . . .
C5 C 0.5388(15) 0.7452(9) 0.6566(6) 0.018(2) Uani 1 1 d . . . . .
H5A H 0.6059 0.7824 0.7152 0.022 Uiso 1 1 calc R U . . .
H5B H 0.3744 0.7394 0.6640 0.022 Uiso 1 1 calc R U . . .
C11 C 0.7140(16) 0.2842(9) 0.7599(5) 0.021(2) Uani 1 1 d . . . . .
C12 C 0.5104(16) 0.3478(9) 0.7462(6) 0.023(2) Uani 1 1 d . . . . .
H12 H 0.4286 0.3334 0.6850 0.027 Uiso 1 1 calc R U . . .
C13 C 0.4426(14) 0.4549(8) 0.8042(5) 0.016(2) Uani 1 1 d . . . . .
H13 H 0.3129 0.5119 0.7838 0.020 Uiso 1 1 calc R U . . .
C14 C 0.5754(13) 0.4953(15) 0.8827(5) 0.0194(17) Uani 1 1 d . . . . .
C15 C 0.7823(14) 0.4280(9) 0.8978(6) 0.020(2) Uani 1 1 d . . . . .
H15 H 0.8944 0.4695 0.9420 0.024 Uiso 1 1 calc R U . . .
C16 C 0.8545(16) 0.3257(9) 0.8382(6) 0.020(2) Uani 1 1 d . . . . .
H16 H 1.0134 0.2942 0.8423 0.024 Uiso 1 1 calc R U . . .
C17 C 0.796(2) 0.1770(10) 0.6966(6) 0.036(3) Uani 1 1 d . . . . .
H17A H 0.7862 0.0900 0.7285 0.054 Uiso 1 1 calc R U . . .
H17B H 0.9529 0.1949 0.6807 0.054 Uiso 1 1 calc R U . . .
H17C H 0.7048 0.1753 0.6388 0.054 Uiso 1 1 calc R U . . .
C18 C 0.4968(17) 0.6076(10) 0.9465(6) 0.026(2) Uani 1 1 d . . . . .
H18 H 0.4106 0.6738 0.9073 0.031 Uiso 1 1 calc R U . . .
C19 C 0.3377(17) 0.5457(11) 1.0181(7) 0.036(3) Uani 1 1 d . . . . .
H19A H 0.2324 0.4854 0.9856 0.054 Uiso 1 1 calc R U . . .
H19B H 0.2543 0.6172 1.0496 0.054 Uiso 1 1 calc R U . . .
H19C H 0.4246 0.4948 1.0651 0.054 Uiso 1 1 calc R U . . .
C20 C 0.6851(18) 0.6815(10) 0.9971(6) 0.032(3) Uani 1 1 d . . . . .
H20A H 0.7590 0.6208 1.0421 0.048 Uiso 1 1 calc R U . . .
H20B H 0.6238 0.7587 1.0309 0.048 Uiso 1 1 calc R U . . .
H20C H 0.7943 0.7127 0.9510 0.048 Uiso 1 1 calc R U . . .
C21 C 1.0326(15) 0.7711(10) 0.8006(6) 0.022(2) Uani 1 1 d . . . . .
N2 N 0.9464(13) 0.6707(8) 0.7834(5) 0.0200(18) Uani 1 1 d . . . . .
S1 S 1.1594(4) 0.9126(3) 0.82568(18) 0.0294(6) Uani 1 1 d . . . . .


_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 2.050(8) . ?
Ru1 O1 2.081(6) . ?
Ru1 C13 2.144(8) . ?
Ru1 N1 2.145(6) . ?
Ru1 C12 2.164(9) . ?
Ru1 C11 2.172(9) . ?
Ru1 C16 2.173(9) . ?
Ru1 C15 2.186(8) . ?
Ru1 C14 2.200(7) . ?
N1 C5 1.487(11) . ?
N1 C2 1.497(11) . ?
N1 H1 1.0000 . ?
O1 C1 1.281(10) . ?
O2 C1 1.242(11) . ?
O3 C4 1.429(10) . ?
O3 H3 0.8400 . ?
C1 C2 1.523(12) . ?
C2 C3 1.523(12) . ?
C2 H2 1.0000 . ?
C3 C4 1.503(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(12) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 C12 1.381(13) . ?
C11 C16 1.444(11) . ?
C11 C17 1.484(13) . ?
C12 C13 1.410(12) . ?
C12 H12 1.0000 . ?
C13 C14 1.417(10) . ?
C13 H13 1.0000 . ?
C14 C15 1.419(13) . ?
C14 C18 1.518(15) . ?
C15 C16 1.396(13) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C20 1.516(13) . ?
C18 C19 1.531(14) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N2 1.149(12) . ?
C21 S1 1.636(11) . ?

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 O1 82.1(3) . . ?
N2 Ru1 C13 124.4(3) . . ?
O1 Ru1 C13 151.9(3) . . ?
N2 Ru1 N1 85.5(3) . . ?
O1 Ru1 N1 79.8(2) . . ?
C13 Ru1 N1 92.3(3) . . ?
N2 Ru1 C12 162.6(3) . . ?
O1 Ru1 C12 114.9(3) . . ?
C13 Ru1 C12 38.2(3) . . ?
N1 Ru1 C12 94.1(3) . . ?
N2 Ru1 C11 152.7(3) . . ?
O1 Ru1 C11 91.7(3) . . ?
C13 Ru1 C11 68.7(3) . . ?
N1 Ru1 C11 119.6(3) . . ?
C12 Ru1 C11 37.2(3) . . ?
N2 Ru1 C16 115.2(3) . . ?
O1 Ru1 C16 96.3(3) . . ?
C13 Ru1 C16 81.2(3) . . ?
N1 Ru1 C16 158.3(3) . . ?
C12 Ru1 C16 68.1(3) . . ?
C11 Ru1 C16 38.8(3) . . ?
N2 Ru1 C15 93.2(3) . . ?
O1 Ru1 C15 124.7(3) . . ?
C13 Ru1 C15 68.1(3) . . ?
N1 Ru1 C15 155.2(3) . . ?
C12 Ru1 C15 79.9(3) . . ?
C11 Ru1 C15 68.6(3) . . ?
C16 Ru1 C15 37.3(3) . . ?
N2 Ru1 C14 96.3(4) . . ?
O1 Ru1 C14 162.4(3) . . ?
C13 Ru1 C14 38.0(3) . . ?
N1 Ru1 C14 117.7(4) . . ?
C12 Ru1 C14 68.5(4) . . ?
C11 Ru1 C14 81.7(5) . . ?
C16 Ru1 C14 68.5(4) . . ?
C15 Ru1 C14 37.7(3) . . ?
C5 N1 C2 107.9(7) . . ?
C5 N1 Ru1 116.7(5) . . ?
C2 N1 Ru1 110.5(5) . . ?
C5 N1 H1 107.1 . . ?
C2 N1 H1 107.1 . . ?
Ru1 N1 H1 107.1 . . ?
C1 O1 Ru1 115.8(5) . . ?
C4 O3 H3 109.5 . . ?
O2 C1 O1 123.2(8) . . ?
O2 C1 C2 118.7(8) . . ?
O1 C1 C2 118.0(8) . . ?
N1 C2 C1 111.9(7) . . ?
N1 C2 C3 105.0(7) . . ?
C1 C2 C3 115.5(8) . . ?
N1 C2 H2 108.1 . . ?
C1 C2 H2 108.1 . . ?
C3 C2 H2 108.1 . . ?
C4 C3 C2 103.9(8) . . ?
C4 C3 H3A 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
O3 C4 C3 110.7(7) . . ?
O3 C4 C5 113.1(7) . . ?
C3 C4 C5 102.3(7) . . ?
O3 C4 H4 110.1 . . ?
C3 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
N1 C5 C4 104.8(7) . . ?
N1 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
N1 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C12 C11 C16 118.5(8) . . ?
C12 C11 C17 122.9(8) . . ?
C16 C11 C17 118.6(9) . . ?
C12 C11 Ru1 71.1(5) . . ?
C16 C11 Ru1 70.6(5) . . ?
C17 C11 Ru1 128.8(7) . . ?
C11 C12 C13 121.6(8) . . ?
C11 C12 Ru1 71.8(5) . . ?
C13 C12 Ru1 70.1(5) . . ?
C11 C12 H12 118.3 . . ?
C13 C12 H12 118.3 . . ?
Ru1 C12 H12 118.3 . . ?
C12 C13 C14 120.8(9) . . ?
C12 C13 Ru1 71.7(5) . . ?
C14 C13 Ru1 73.1(5) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
Ru1 C13 H13 119.2 . . ?
C13 C14 C15 117.5(9) . . ?
C13 C14 C18 120.3(9) . . ?
C15 C14 C18 122.3(7) . . ?
C13 C14 Ru1 68.8(4) . . ?
C15 C14 Ru1 70.6(5) . . ?
C18 C14 Ru1 131.3(9) . . ?
C16 C15 C14 121.9(8) . . ?
C16 C15 Ru1 70.8(5) . . ?
C14 C15 Ru1 71.7(5) . . ?
C16 C15 H15 118.2 . . ?
C14 C15 H15 118.2 . . ?
Ru1 C15 H15 118.2 . . ?
C15 C16 C11 119.7(8) . . ?
C15 C16 Ru1 71.8(5) . . ?
C11 C16 Ru1 70.5(5) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
Ru1 C16 H16 119.6 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C14 114.0(8) . . ?
C20 C18 C19 110.1(7) . . ?
C14 C18 C19 107.4(8) . . ?
C20 C18 H18 108.4 . . ?
C14 C18 H18 108.4 . . ?
C19 C18 H18 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 S1 179.0(9) . . ?
C21 N2 Ru1 175.6(8) . . ?

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 O1 C1 O2 158.8(6) . . . . ?
Ru1 O1 C1 C2 -22.7(9) . . . . ?
C5 N1 C2 C1 131.4(7) . . . . ?
Ru1 N1 C2 C1 2.8(8) . . . . ?
C5 N1 C2 C3 5.4(8) . . . . ?
Ru1 N1 C2 C3 -123.3(5) . . . . ?
O2 C1 C2 N1 -168.6(7) . . . . ?
O1 C1 C2 N1 12.8(10) . . . . ?
O2 C1 C2 C3 -48.6(11) . . . . ?
O1 C1 C2 C3 132.9(8) . . . . ?
N1 C2 C3 C4 -28.2(8) . . . . ?
C1 C2 C3 C4 -152.0(7) . . . . ?
C2 C3 C4 O3 -81.1(8) . . . . ?
C2 C3 C4 C5 39.8(8) . . . . ?
C2 N1 C5 C4 19.3(8) . . . . ?
Ru1 N1 C5 C4 144.3(6) . . . . ?
O3 C4 C5 N1 82.7(9) . . . . ?
C3 C4 C5 N1 -36.5(8) . . . . ?
C16 C11 C12 C13 2.7(13) . . . . ?
C17 C11 C12 C13 -176.1(8) . . . . ?
Ru1 C11 C12 C13 -51.5(7) . . . . ?
C16 C11 C12 Ru1 54.2(8) . . . . ?
C17 C11 C12 Ru1 -124.6(9) . . . . ?
C11 C12 C13 C14 -4.2(13) . . . . ?
Ru1 C12 C13 C14 -56.4(8) . . . . ?
C11 C12 C13 Ru1 52.2(8) . . . . ?
C12 C13 C14 C15 2.7(14) . . . . ?
Ru1 C13 C14 C15 -53.0(8) . . . . ?
C12 C13 C14 C18 -177.9(9) . . . . ?
Ru1 C13 C14 C18 126.4(11) . . . . ?
C12 C13 C14 Ru1 55.7(8) . . . . ?
C13 C14 C15 C16 0.0(15) . . . . ?
C18 C14 C15 C16 -179.3(9) . . . . ?
Ru1 C14 C15 C16 -52.1(9) . . . . ?
C13 C14 C15 Ru1 52.1(8) . . . . ?
C18 C14 C15 Ru1 -127.2(11) . . . . ?
C14 C15 C16 C11 -1.3(15) . . . . ?
Ru1 C15 C16 C11 -53.8(8) . . . . ?
C14 C15 C16 Ru1 52.5(9) . . . . ?
C12 C11 C16 C15 0.0(14) . . . . ?
C17 C11 C16 C15 178.9(9) . . . . ?
Ru1 C11 C16 C15 54.4(8) . . . . ?
C12 C11 C16 Ru1 -54.4(8) . . . . ?
C17 C11 C16 Ru1 124.4(8) . . . . ?
C13 C14 C18 C20 -153.9(9) . . . . ?
C15 C14 C18 C20 25.4(14) . . . . ?
Ru1 C14 C18 C20 -66.4(10) . . . . ?
C13 C14 C18 C19 83.9(11) . . . . ?
C15 C14 C18 C19 -96.8(12) . . . . ?
Ru1 C14 C18 C19 171.3(6) . . . . ?

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
N1 H1 O2 1.00 2.11 2.942(9) 139.3 1_455
O3 H3 O2 0.84 2.00 2.829(9) 167.7 1_455
C5 H5A N2 0.99 2.50 3.095(11) 118.4 .
C5 H5B O2 0.99 2.57 3.073(10) 111.4 1_455

_refine_diff_density_max         1.393
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.123


####################################################################### 
# 
# 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_2e
_database_code_depnum_ccdc_archive 'CCDC 2104833'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2021-10-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT342_2e                  
;
PROBLEM: Low Bond Precision on C-C Bonds
RESPONSE: The crystal is a thin needle and its 
quality is not very high. 
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H22 I N O3 Ru'
_chemical_formula_weight         492.30

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'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4798(7)
_cell_length_b                   11.7879(8)
_cell_length_c                   13.2428(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1635.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9786
_cell_measurement_theta_min      2.9735
_cell_measurement_theta_max      36.8175

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.999
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.854
_shelx_estimated_absorpt_T_min   0.613
_shelx_estimated_absorpt_T_max   0.726
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.2679
_exptl_absorpt_correction_T_max  0.4389
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1566 (selected reflections only, before parameter refinement)
 R(int) =  0.0718 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21646
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         25.975
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3216
_reflns_number_gt                3214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+35.7129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.04(9)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3216
_refine_ls_number_parameters     193
_refine_ls_number_restraints     145
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1324
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.395
_refine_ls_restrained_S_all      1.384
_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_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 0.23979(11) 0.18754(9) 0.69756(8) 0.0092(3) Uani 1 1 d . . . . .
I1 I 0.11440(10) 0.01616(8) 0.59858(8) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.1882(11) 0.2990(11) 0.5765(9) 0.010(2) Uani 1 1 d . U . . .
H1 H 0.0930 0.3008 0.5727 0.013 Uiso 1 1 calc R U . . .
O1 O 0.3904(10) 0.1654(9) 0.5898(9) 0.021(2) Uani 1 1 d . . . . .
O2 O 0.4245(12) 0.1631(12) 0.4239(10) 0.029(3) Uani 1 1 d . U . . .
O3 O 0.0918(14) 0.5037(14) 0.4544(12) 0.051(4) Uani 1 1 d . U . . .
H3 H 0.0484 0.4503 0.4302 0.076 Uiso 1 1 calc DR U . . .
C1 C 0.3586(14) 0.1897(15) 0.4976(12) 0.018(3) Uani 1 1 d . U . . .
C2 C 0.2356(15) 0.2550(13) 0.4799(11) 0.014(3) Uani 1 1 d . U . . .
H2 H 0.1702 0.2044 0.4485 0.017 Uiso 1 1 calc R U . . .
C3 C 0.2586(19) 0.3612(15) 0.4116(13) 0.027(3) Uani 1 1 d . U . . .
H3A H 0.3493 0.3660 0.3912 0.033 Uiso 1 1 calc R U . . .
H3B H 0.2052 0.3571 0.3500 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2214(17) 0.4637(17) 0.4753(14) 0.028(3) Uani 1 1 d . U . . .
H4 H 0.2838 0.5267 0.4641 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2340(16) 0.4189(13) 0.5829(12) 0.020(3) Uani 1 1 d . U . . .
H5A H 0.3238 0.4219 0.6059 0.024 Uiso 1 1 calc R U . . .
H5B H 0.1806 0.4635 0.6301 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1036(17) 0.1924(16) 0.8257(12) 0.022(3) Uani 1 1 d . U . . .
C12 C 0.1923(17) 0.0987(15) 0.8368(13) 0.022(3) Uani 1 1 d . U . . .
H12 H 0.1576 0.0199 0.8311 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3251(17) 0.1123(14) 0.8345(12) 0.018(3) Uani 1 1 d . U . . .
H13 H 0.3811 0.0440 0.8282 0.022 Uiso 1 1 calc R U . . .
C14 C 0.3771(16) 0.2209(12) 0.8186(11) 0.015(3) Uani 1 1 d . U . . .
C15 C 0.2959(13) 0.3159(13) 0.8099(11) 0.013(3) Uani 1 1 d . U . . .
H15 H 0.3320 0.3898 0.7863 0.015 Uiso 1 1 calc R U . . .
C16 C 0.1590(13) 0.3001(13) 0.8101(11) 0.012(3) Uani 1 1 d . U . . .
H16 H 0.1033 0.3640 0.7873 0.014 Uiso 1 1 calc R U . . .
C17 C -0.0348(17) 0.1779(18) 0.8234(13) 0.029(4) Uani 1 1 d . U . . .
H17A H -0.0559 0.0981 0.8356 0.034 Uiso 1 1 calc R U . . .
H17B H -0.0739 0.2251 0.8759 0.034 Uiso 1 1 calc R U . . .
H17C H -0.0675 0.2008 0.7571 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5226(16) 0.2334(15) 0.8107(13) 0.020(3) Uani 1 1 d . U . . .
H18 H 0.5544 0.1660 0.7723 0.024 Uiso 1 1 calc R U . . .
C19 C 0.5690(16) 0.3370(15) 0.7553(12) 0.020(3) Uani 1 1 d . U . . .
H19A H 0.5601 0.4037 0.7990 0.030 Uiso 1 1 calc R U . . .
H19B H 0.5182 0.3478 0.6939 0.030 Uiso 1 1 calc R U . . .
H19C H 0.6590 0.3271 0.7371 0.030 Uiso 1 1 calc R U . . .
C20 C 0.5803(18) 0.2260(16) 0.9167(13) 0.026(4) Uani 1 1 d . U . . .
H20A H 0.6735 0.2225 0.9116 0.039 Uiso 1 1 calc R U . . .
H20B H 0.5487 0.1577 0.9506 0.039 Uiso 1 1 calc R U . . .
H20C H 0.5557 0.2932 0.9557 0.039 Uiso 1 1 calc R U . . .


_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 N1 2.142(12) . ?
Ru1 O1 2.144(11) . ?
Ru1 C16 2.168(15) . ?
Ru1 C12 2.178(17) . ?
Ru1 C14 2.190(15) . ?
Ru1 C15 2.202(15) . ?
Ru1 C13 2.208(17) . ?
Ru1 C11 2.218(16) . ?
Ru1 I1 2.7434(15) . ?
N1 C2 1.466(18) . ?
N1 C5 1.495(19) . ?
N1 H1 1.0000 . ?
O1 C1 1.30(2) . ?
O2 C1 1.24(2) . ?
O3 C4 1.46(2) . ?
O3 H3 0.8400 . ?
C1 C2 1.52(2) . ?
C2 C3 1.56(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.52(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.52(2) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C11 C16 1.41(2) . ?
C11 C12 1.45(3) . ?
C11 C17 1.46(2) . ?
C12 C13 1.40(2) . ?
C12 H12 1.0000 . ?
C13 C14 1.41(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.41(2) . ?
C14 C18 1.54(2) . ?
C15 C16 1.446(19) . ?
C15 H15 1.0000 . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.51(2) . ?
C18 C20 1.53(2) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
N1 Ru1 O1 76.2(4) . . ?
N1 Ru1 C16 92.4(5) . . ?
O1 Ru1 C16 145.1(5) . . ?
N1 Ru1 C12 150.6(6) . . ?
O1 Ru1 C12 132.3(6) . . ?
C16 Ru1 C12 67.9(6) . . ?
N1 Ru1 C14 127.1(5) . . ?
O1 Ru1 C14 91.5(5) . . ?
C16 Ru1 C14 69.1(5) . . ?
C12 Ru1 C14 67.5(6) . . ?
N1 Ru1 C15 98.7(5) . . ?
O1 Ru1 C15 109.7(5) . . ?
C16 Ru1 C15 38.7(5) . . ?
C12 Ru1 C15 79.6(6) . . ?
C14 Ru1 C15 37.5(5) . . ?
N1 Ru1 C13 164.4(6) . . ?
O1 Ru1 C13 101.5(6) . . ?
C16 Ru1 C13 80.7(6) . . ?
C12 Ru1 C13 37.3(6) . . ?
C14 Ru1 C13 37.3(6) . . ?
C15 Ru1 C13 67.2(6) . . ?
N1 Ru1 C11 113.2(6) . . ?
O1 Ru1 C11 170.5(6) . . ?
C16 Ru1 C11 37.5(6) . . ?
C12 Ru1 C11 38.5(7) . . ?
C14 Ru1 C11 81.8(6) . . ?
C15 Ru1 C11 68.7(6) . . ?
C13 Ru1 C11 69.1(7) . . ?
N1 Ru1 I1 88.5(3) . . ?
O1 Ru1 I1 86.8(3) . . ?
C16 Ru1 I1 126.3(4) . . ?
C12 Ru1 I1 86.6(5) . . ?
C14 Ru1 I1 142.8(4) . . ?
C15 Ru1 I1 163.1(4) . . ?
C13 Ru1 I1 106.9(4) . . ?
C11 Ru1 I1 94.4(4) . . ?
C2 N1 C5 106.0(12) . . ?
C2 N1 Ru1 110.5(9) . . ?
C5 N1 Ru1 117.1(9) . . ?
C2 N1 H1 107.6 . . ?
C5 N1 H1 107.6 . . ?
Ru1 N1 H1 107.6 . . ?
C1 O1 Ru1 114.2(9) . . ?
C4 O3 H3 109.5 . . ?
O2 C1 O1 122.9(15) . . ?
O2 C1 C2 118.8(14) . . ?
O1 C1 C2 118.4(13) . . ?
N1 C2 C1 109.4(12) . . ?
N1 C2 C3 105.9(13) . . ?
C1 C2 C3 111.4(14) . . ?
N1 C2 H2 110.0 . . ?
C1 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C4 C3 C2 105.9(14) . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
O3 C4 C3 112.8(16) . . ?
O3 C4 C5 111.6(14) . . ?
C3 C4 C5 102.8(15) . . ?
O3 C4 H4 109.8 . . ?
C3 C4 H4 109.8 . . ?
C5 C4 H4 109.8 . . ?
N1 C5 C4 104.3(13) . . ?
N1 C5 H5A 110.9 . . ?
C4 C5 H5A 110.9 . . ?
N1 C5 H5B 110.9 . . ?
C4 C5 H5B 110.9 . . ?
H5A C5 H5B 108.9 . . ?
C16 C11 C12 115.8(15) . . ?
C16 C11 C17 120.7(17) . . ?
C12 C11 C17 123.3(17) . . ?
C16 C11 Ru1 69.3(9) . . ?
C12 C11 Ru1 69.2(10) . . ?
C17 C11 Ru1 128.3(12) . . ?
C13 C12 C11 123.2(16) . . ?
C13 C12 Ru1 72.5(11) . . ?
C11 C12 Ru1 72.2(9) . . ?
C13 C12 H12 117.8 . . ?
C11 C12 H12 117.8 . . ?
Ru1 C12 H12 117.8 . . ?
C12 C13 C14 119.5(16) . . ?
C12 C13 Ru1 70.2(10) . . ?
C14 C13 Ru1 70.6(9) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
Ru1 C13 H13 119.5 . . ?
C13 C14 C15 120.0(15) . . ?
C13 C14 C18 118.8(14) . . ?
C15 C14 C18 121.2(14) . . ?
C13 C14 Ru1 72.1(9) . . ?
C15 C14 Ru1 71.7(9) . . ?
C18 C14 Ru1 128.3(11) . . ?
C14 C15 C16 119.7(14) . . ?
C14 C15 Ru1 70.8(9) . . ?
C16 C15 Ru1 69.4(9) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
Ru1 C15 H15 119.2 . . ?
C11 C16 C15 121.6(15) . . ?
C11 C16 Ru1 73.2(9) . . ?
C15 C16 Ru1 71.9(9) . . ?
C11 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
Ru1 C16 H16 118.8 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C20 111.4(15) . . ?
C19 C18 C14 115.6(14) . . ?
C20 C18 C14 108.9(14) . . ?
C19 C18 H18 106.8 . . ?
C20 C18 H18 106.8 . . ?
C14 C18 H18 106.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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 O1 C1 O2 -166.7(13) . . . . ?
Ru1 O1 C1 C2 14.1(18) . . . . ?
C5 N1 C2 C1 96.8(14) . . . . ?
Ru1 N1 C2 C1 -31.1(14) . . . . ?
C5 N1 C2 C3 -23.4(15) . . . . ?
Ru1 N1 C2 C3 -151.2(10) . . . . ?
O2 C1 C2 N1 -167.6(14) . . . . ?
O1 C1 C2 N1 12(2) . . . . ?
O2 C1 C2 C3 -51(2) . . . . ?
O1 C1 C2 C3 128.4(16) . . . . ?
N1 C2 C3 C4 0.0(17) . . . . ?
C1 C2 C3 C4 -118.9(15) . . . . ?
C2 C3 C4 O3 -97.7(16) . . . . ?
C2 C3 C4 C5 22.6(17) . . . . ?
C2 N1 C5 C4 38.3(16) . . . . ?
Ru1 N1 C5 C4 162.2(10) . . . . ?
O3 C4 C5 N1 83.9(17) . . . . ?
C3 C4 C5 N1 -37.1(16) . . . . ?
C16 C11 C12 C13 1(3) . . . . ?
C17 C11 C12 C13 177.1(17) . . . . ?
Ru1 C11 C12 C13 54.2(17) . . . . ?
C16 C11 C12 Ru1 -52.9(12) . . . . ?
C17 C11 C12 Ru1 123.0(15) . . . . ?
C11 C12 C13 C14 -2(3) . . . . ?
Ru1 C12 C13 C14 52.5(15) . . . . ?
C11 C12 C13 Ru1 -54.0(16) . . . . ?
C12 C13 C14 C15 3(2) . . . . ?
Ru1 C13 C14 C15 55.4(13) . . . . ?
C12 C13 C14 C18 -176.7(16) . . . . ?
Ru1 C13 C14 C18 -124.4(14) . . . . ?
C12 C13 C14 Ru1 -52.3(15) . . . . ?
C13 C14 C15 C16 -4(2) . . . . ?
C18 C14 C15 C16 175.4(14) . . . . ?
Ru1 C14 C15 C16 51.1(13) . . . . ?
C13 C14 C15 Ru1 -55.5(13) . . . . ?
C18 C14 C15 Ru1 124.2(14) . . . . ?
C12 C11 C16 C15 -3(2) . . . . ?
C17 C11 C16 C15 -178.6(15) . . . . ?
Ru1 C11 C16 C15 -55.5(13) . . . . ?
C12 C11 C16 Ru1 52.8(13) . . . . ?
C17 C11 C16 Ru1 -123.1(15) . . . . ?
C14 C15 C16 C11 4(2) . . . . ?
Ru1 C15 C16 C11 56.1(14) . . . . ?
C14 C15 C16 Ru1 -51.8(13) . . . . ?
C13 C14 C18 C19 157.2(15) . . . . ?
C15 C14 C18 C19 -23(2) . . . . ?
Ru1 C14 C18 C19 68.0(18) . . . . ?
C13 C14 C18 C20 -76.6(18) . . . . ?
C15 C14 C18 C20 103.6(17) . . . . ?
Ru1 C14 C18 C20 -165.8(11) . . . . ?

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
N1 H1 O2 1.00 1.82 2.799(17) 167.0 4_456
O3 H3 O1 0.84 2.16 2.961(17) 159.1 4_456
C3 H3A I1 0.99 3.11 4.002(19) 150.7 4_556

_refine_diff_density_max         1.218
_refine_diff_density_min         -1.886
_refine_diff_density_rms         0.258


####################################################################### 
# 
# 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_RuN3
_database_code_depnum_ccdc_archive 'CCDC 2104834'
loop_
_audit_author_name
_audit_author_address
'Stefano Zacchini'
;Universita di Bologna
Italy
;
_audit_update_record             
;
2021-08-23 deposited with the CCDC.	2021-10-22 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          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 N12 Ru2'
_chemical_formula_weight         638.68

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'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   8.0847(4)
_cell_length_b                   8.2571(5)
_cell_length_c                   9.7821(5)
_cell_angle_alpha                83.3520(10)
_cell_angle_beta                 85.0850(10)
_cell_angle_gamma                77.2420(10)
_cell_volume                     631.39(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.588
_cell_measurement_theta_max      34.845

_exptl_crystal_description       prism
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.680
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    1.229
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.847
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6414
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_process_details   
; 
 Data were corrected for Lorentz polarization and absorption
 effects (empirical absorption correction SADABS).
 R(int) =  0.1081 (selected reflections only, before parameter refinement)
 R(int) =  0.0339 (selected reflections only, after parameter refinement)
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON100 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9239
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3024
_reflns_number_gt                2959
_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       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'APEX3 (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEPIII (Johnson, 1996)'
_computing_publication_material  'XCIF 2014/2 (Bruker AXS, 2014)'
_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)+(0.0175P)²+0.5034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3024
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0177
_refine_ls_wR_factor_ref         0.0457
_refine_ls_wR_factor_gt          0.0454
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.001
_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_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 0.1426(2) 0.8104(2) 0.53254(18) 0.0177(3) Uani 1 1 d . . . . .
C2 C 0.0553(2) 0.7453(2) 0.43916(18) 0.0176(3) Uani 1 1 d . . . . .
H2 H -0.0324 0.6803 0.4762 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1169(2) 0.7396(2) 0.29852(18) 0.0160(3) Uani 1 1 d . . . . .
H3 H 0.0709 0.6695 0.2407 0.019 Uiso 1 1 calc R U . . .
C4 C 0.2635(2) 0.7989(2) 0.24693(17) 0.0140(3) Uani 1 1 d . . . . .
C5 C 0.3485(2) 0.8666(2) 0.34274(18) 0.0152(3) Uani 1 1 d . . . . .
H5 H 0.4650 0.8862 0.3151 0.018 Uiso 1 1 calc R U . . .
C6 C 0.2884(2) 0.8751(2) 0.48205(18) 0.0172(3) Uani 1 1 d . . . . .
H6 H 0.3636 0.8997 0.5495 0.021 Uiso 1 1 calc R U . . .
C7 C 0.0873(3) 0.8029(3) 0.68325(19) 0.0260(4) Uani 1 1 d . . . . .
H7A H 0.1870 0.7852 0.7378 0.039 Uiso 1 1 calc R U . . .
H7B H 0.0287 0.7105 0.7075 0.039 Uiso 1 1 calc R U . . .
H7C H 0.0099 0.9081 0.7028 0.039 Uiso 1 1 calc R U . . .
C8 C 0.3324(2) 0.7924(2) 0.09796(17) 0.0169(3) Uani 1 1 d . . . . .
H8 H 0.4591 0.7719 0.0970 0.020 Uiso 1 1 calc R U . . .
C9 C 0.2874(3) 0.6525(3) 0.0289(2) 0.0269(4) Uani 1 1 d . . . . .
H9A H 0.3201 0.5465 0.0864 0.040 Uiso 1 1 calc R U . . .
H9B H 0.3485 0.6444 -0.0618 0.040 Uiso 1 1 calc R U . . .
H9C H 0.1647 0.6766 0.0180 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2699(2) 0.9640(2) 0.01895(19) 0.0215(4) Uani 1 1 d . . . . .
H10A H 0.1457 0.9875 0.0181 0.032 Uiso 1 1 calc R U . . .
H10B H 0.3196 0.9640 -0.0760 0.032 Uiso 1 1 calc R U . . .
H10C H 0.3044 1.0500 0.0643 0.032 Uiso 1 1 calc R U . . .
N1 N 0.2763(2) 0.38396(19) 0.39933(17) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.36431(19) 0.29808(18) 0.31986(15) 0.0164(3) Uani 1 1 d . . . . .
N3 N 0.4453(2) 0.2094(2) 0.24401(19) 0.0283(4) Uani 1 1 d . . . . .
N4 N 0.58206(17) 0.50699(17) 0.37913(15) 0.0129(3) Uani 1 1 d . . . . .
N5 N 0.67373(18) 0.57957(18) 0.30033(15) 0.0149(3) Uani 1 1 d . . . . .
N6 N 0.7595(2) 0.6426(2) 0.22325(18) 0.0286(4) Uani 1 1 d . . . . .
Ru1 Ru 0.32293(2) 0.61847(2) 0.42793(2) 0.00960(5) Uani 1 1 d . . . . .


_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
C1 C2 1.420(3) . ?
C1 C6 1.427(3) . ?
C1 C7 1.502(2) . ?
C1 Ru1 2.1872(17) . ?
C2 C3 1.425(2) . ?
C2 Ru1 2.1854(16) . ?
C2 H2 1.0000 . ?
C3 C4 1.413(2) . ?
C3 Ru1 2.1700(16) . ?
C3 H3 1.0000 . ?
C4 C5 1.437(2) . ?
C4 C8 1.517(2) . ?
C4 Ru1 2.1916(16) . ?
C5 C6 1.411(2) . ?
C5 Ru1 2.1675(16) . ?
C5 H5 1.0000 . ?
C6 Ru1 2.1959(17) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.527(3) . ?
C8 C10 1.535(2) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N1 N2 1.193(2) . ?
N1 Ru1 2.1063(15) . ?
N2 N3 1.160(2) . ?
N4 N5 1.222(2) . ?
N4 Ru1 2.1314(14) . ?
N4 Ru1 2.1610(14) 2_666 ?
N5 N6 1.140(2) . ?
Ru1 N4 2.1610(14) 2_666 ?

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 C6 118.95(16) . . ?
C2 C1 C7 120.23(17) . . ?
C6 C1 C7 120.75(17) . . ?
C2 C1 Ru1 70.99(10) . . ?
C6 C1 Ru1 71.34(10) . . ?
C7 C1 Ru1 126.75(12) . . ?
C1 C2 C3 120.05(16) . . ?
C1 C2 Ru1 71.13(9) . . ?
C3 C2 Ru1 70.32(9) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
Ru1 C2 H2 119.2 . . ?
C4 C3 C2 122.01(16) . . ?
C4 C3 Ru1 71.93(9) . . ?
C2 C3 Ru1 71.49(9) . . ?
C4 C3 H3 118.3 . . ?
C2 C3 H3 118.3 . . ?
Ru1 C3 H3 118.3 . . ?
C3 C4 C5 117.01(15) . . ?
C3 C4 C8 122.90(15) . . ?
C5 C4 C8 120.10(15) . . ?
C3 C4 Ru1 70.28(9) . . ?
C5 C4 Ru1 69.85(9) . . ?
C8 C4 Ru1 130.46(12) . . ?
C6 C5 C4 121.86(16) . . ?
C6 C5 Ru1 72.23(10) . . ?
C4 C5 Ru1 71.66(9) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
Ru1 C5 H5 118.5 . . ?
C5 C6 C1 120.06(16) . . ?
C5 C6 Ru1 70.04(9) . . ?
C1 C6 Ru1 70.67(10) . . ?
C5 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
Ru1 C6 H6 119.1 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 C9 113.31(15) . . ?
C4 C8 C10 108.57(14) . . ?
C9 C8 C10 111.78(15) . . ?
C4 C8 H8 107.6 . . ?
C9 C8 H8 107.6 . . ?
C10 C8 H8 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 N1 Ru1 120.67(12) . . ?
N3 N2 N1 176.90(18) . . ?
N5 N4 Ru1 121.88(11) . . ?
N5 N4 Ru1 119.03(11) . 2_666 ?
Ru1 N4 Ru1 104.97(6) . 2_666 ?
N6 N5 N4 177.27(19) . . ?
N1 Ru1 N4 84.78(6) . . ?
N1 Ru1 N4 83.98(6) . 2_666 ?
N4 Ru1 N4 75.03(6) . 2_666 ?
N1 Ru1 C5 149.39(7) . . ?
N4 Ru1 C5 94.12(6) . . ?
N4 Ru1 C5 125.35(6) 2_666 . ?
N1 Ru1 C3 89.91(7) . . ?
N4 Ru1 C3 131.81(6) . . ?
N4 Ru1 C3 151.89(6) 2_666 . ?
C5 Ru1 C3 68.14(7) . . ?
N1 Ru1 C2 95.15(7) . . ?
N4 Ru1 C2 169.96(6) . . ?
N4 Ru1 C2 114.97(6) 2_666 . ?
C5 Ru1 C2 80.81(7) . . ?
C3 Ru1 C2 38.19(6) . . ?
N1 Ru1 C1 124.26(7) . . ?
N4 Ru1 C1 147.35(6) . . ?
N4 Ru1 C1 92.10(6) 2_666 . ?
C5 Ru1 C1 68.74(7) . . ?
C3 Ru1 C1 68.87(7) . . ?
C2 Ru1 C1 37.89(7) . . ?
N1 Ru1 C4 111.73(6) . . ?
N4 Ru1 C4 101.57(6) . . ?
N4 Ru1 C4 163.78(6) 2_666 . ?
C5 Ru1 C4 38.49(6) . . ?
C3 Ru1 C4 37.79(6) . . ?
C2 Ru1 C4 69.09(6) . . ?
C1 Ru1 C4 82.42(6) . . ?
N1 Ru1 C6 162.10(7) . . ?
N4 Ru1 C6 112.85(6) . . ?
N4 Ru1 C6 97.24(6) 2_666 . ?
C5 Ru1 C6 37.73(7) . . ?
C3 Ru1 C6 80.61(7) . . ?
C2 Ru1 C6 68.05(7) . . ?
C1 Ru1 C6 37.99(7) . . ?
C4 Ru1 C6 69.14(6) . . ?

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
C6 C1 C2 C3 2.2(2) . . . . ?
C7 C1 C2 C3 -174.60(16) . . . . ?
Ru1 C1 C2 C3 -52.48(14) . . . . ?
C6 C1 C2 Ru1 54.73(14) . . . . ?
C7 C1 C2 Ru1 -122.12(16) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
Ru1 C2 C3 C4 -53.48(15) . . . . ?
C1 C2 C3 Ru1 52.85(14) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
Ru1 C3 C4 C5 -53.59(13) . . . . ?
C2 C3 C4 C8 179.38(16) . . . . ?
Ru1 C3 C4 C8 126.09(16) . . . . ?
C2 C3 C4 Ru1 53.29(15) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C8 C4 C5 C6 179.89(15) . . . . ?
Ru1 C4 C5 C6 -54.22(14) . . . . ?
C3 C4 C5 Ru1 53.80(13) . . . . ?
C8 C4 C5 Ru1 -125.89(15) . . . . ?
C4 C5 C6 C1 2.1(2) . . . . ?
Ru1 C5 C6 C1 -51.90(14) . . . . ?
C4 C5 C6 Ru1 53.97(14) . . . . ?
C2 C1 C6 C5 -2.9(2) . . . . ?
C7 C1 C6 C5 173.88(16) . . . . ?
Ru1 C1 C6 C5 51.61(14) . . . . ?
C2 C1 C6 Ru1 -54.56(14) . . . . ?
C7 C1 C6 Ru1 122.27(16) . . . . ?
C3 C4 C8 C9 -26.8(2) . . . . ?
C5 C4 C8 C9 152.90(16) . . . . ?
Ru1 C4 C8 C9 64.6(2) . . . . ?
C3 C4 C8 C10 98.06(19) . . . . ?
C5 C4 C8 C10 -82.27(19) . . . . ?
Ru1 C4 C8 C10 -170.60(13) . . . . ?

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.083





