# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1498893'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2016-10-05 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            'C27 H28 Cl N3 O2 Ru'
_chemical_formula_weight         563.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   11.9632(4)
_cell_length_b                   12.8382(4)
_cell_length_c                   18.2364(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.636(2)
_cell_angle_gamma                90
_cell_volume                     2654.00(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4448
_cell_measurement_theta_min      4.882
_cell_measurement_theta_max      52.424

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.719
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27173
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.443
_diffrn_reflns_theta_max         29.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7681
_reflns_number_gt                3885
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0895P)²+0.5610P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7681
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1388
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1839
_refine_ls_wR_factor_gt          0.1505
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 0.74569(3) 0.06223(3) 0.78529(2) 0.05031(16) Uani 1 1 d . . . . .
Cl2 Cl 0.66403(11) 0.20682(10) 0.70137(8) 0.0776(4) Uani 1 1 d . . . . .
N1 N 0.6796(3) -0.0250(3) 0.6847(2) 0.0506(9) Uani 1 1 d . . . . .
O1 O 0.5749(3) 0.0270(3) 0.78031(18) 0.0626(8) Uani 1 1 d . . . . .
C7 C 0.5208(4) -0.0290(3) 0.7213(3) 0.0507(11) Uani 1 1 d . . . . .
C1 C 0.8555(5) -0.0445(4) 0.8679(3) 0.0665(14) Uani 1 1 d . . . . .
H1 H 0.8475 -0.1158 0.8737 0.080 Uiso 1 1 calc R U . . .
C4 C 0.8860(4) 0.1659(4) 0.8519(3) 0.0610(12) Uani 1 1 d . . . . .
H4 H 0.8963 0.2371 0.8473 0.073 Uiso 1 1 calc R U . . .
C3 C 0.8254(4) 0.1325(4) 0.9004(3) 0.0609(12) Uani 1 1 d . . . . .
H3 H 0.7973 0.1809 0.9282 0.073 Uiso 1 1 calc R U . . .
C5 C 0.9336(4) 0.0967(4) 0.8085(3) 0.0628(13) Uani 1 1 d . . . . .
C6 C 0.9171(4) -0.0095(4) 0.8186(3) 0.0639(13) Uani 1 1 d . . . . .
H6 H 0.9476 -0.0580 0.7922 0.077 Uiso 1 1 calc R U . . .
C2 C 0.8057(4) 0.0239(4) 0.9083(3) 0.0641(13) Uani 1 1 d . . . . .
N2 N 0.5653(3) -0.0610(3) 0.6690(2) 0.0540(9) Uani 1 1 d . . . . .
C8 C 0.3983(4) -0.0633(3) 0.7148(3) 0.0554(11) Uani 1 1 d . . . . .
C10 C 0.2401(5) -0.0749(4) 0.7690(3) 0.0753(16) Uani 1 1 d . . . . .
H10 H 0.2101 -0.0600 0.8090 0.090 Uiso 1 1 calc R U . . .
C9 C 0.3523(5) -0.0421(4) 0.7741(3) 0.0710(14) Uani 1 1 d . . . . .
H9 H 0.3973 -0.0056 0.8175 0.085 Uiso 1 1 calc R U . . .
C13 C 0.3295(5) -0.1162(5) 0.6526(3) 0.0788(16) Uani 1 1 d . . . . .
H13 H 0.3594 -0.1309 0.6125 0.095 Uiso 1 1 calc R U . . .
C11 C 0.1732(4) -0.1284(4) 0.7063(3) 0.0690(14) Uani 1 1 d . . . . .
C12 C 0.2165(4) -0.1492(5) 0.6460(3) 0.0829(17) Uani 1 1 d . . . . .
H12 H 0.1709 -0.1846 0.6021 0.099 Uiso 1 1 calc R U . . .
O2 O 0.0631(3) -0.1571(3) 0.7061(2) 0.0872(11) Uani 1 1 d . . . . .
C17 C 0.0131(5) -0.2484(5) 0.6652(3) 0.0949(19) Uani 1 1 d . . . . .
H17A H -0.0103 -0.2351 0.6105 0.142 Uiso 1 1 calc R U . . .
H17B H -0.0546 -0.2686 0.6792 0.142 Uiso 1 1 calc R U . . .
H17C H 0.0704 -0.3035 0.6780 0.142 Uiso 1 1 calc R U . . .
C16 C 0.7329(6) -0.0193(7) 0.9552(4) 0.103(2) Uani 1 1 d . . . . .
H16 H 0.6877 -0.0815 0.9324 0.124 Uiso 1 1 calc R U . . .
C14 C 0.9959(5) 0.1359(5) 0.7544(3) 0.0899(18) Uani 1 1 d . . . . .
H14A H 1.0764 0.1516 0.7831 0.135 Uiso 1 1 calc R U . . .
H14B H 0.9574 0.1978 0.7289 0.135 Uiso 1 1 calc R U . . .
H14C H 0.9936 0.0834 0.7164 0.135 Uiso 1 1 calc R U . . .
N3 N 0.5596(4) -0.1547(3) 0.4484(2) 0.0639(11) Uani 1 1 d . . . . .
C19 C 0.7282(5) -0.0412(4) 0.6321(3) 0.0524(12) Uani 1 1 d . . . . .
C20 C 0.6799(4) -0.0862(3) 0.5573(3) 0.0526(11) Uani 1 1 d . . . . .
C21 C 0.5659(4) -0.1165(3) 0.5170(3) 0.0559(11) Uani 1 1 d . . . . .
H21 H 0.5023 -0.1108 0.5356 0.067 Uiso 1 1 calc R U . . .
C23 C 0.6685(5) -0.1523(4) 0.4378(3) 0.0628(13) Uani 1 1 d . . . . .
C22 C 0.7481(4) -0.1063(4) 0.5062(3) 0.0570(11) Uani 1 1 d . . . . .
C27 C 0.8668(5) -0.0918(4) 0.5094(3) 0.0734(15) Uani 1 1 d . . . . .
H27 H 0.9205 -0.0592 0.5516 0.088 Uiso 1 1 calc R U . . .
C24 C 0.7039(6) -0.1856(5) 0.3769(3) 0.0888(17) Uani 1 1 d . . . . .
H24 H 0.6509 -0.2162 0.3334 0.107 Uiso 1 1 calc R U . . .
C26 C 0.9013(5) -0.1271(5) 0.4483(4) 0.0921(18) Uani 1 1 d . . . . .
H26 H 0.9799 -0.1208 0.4509 0.110 Uiso 1 1 calc R U . . .
C25 C 0.8208(7) -0.1720(6) 0.3829(4) 0.100(2) Uani 1 1 d . . . . .
H25 H 0.8467 -0.1933 0.3423 0.120 Uiso 1 1 calc R U . . .
C29 C 0.6618(14) 0.0606(11) 0.9792(8) 0.238(7) Uani 1 1 d . . . . .
H29A H 0.6231 0.0292 1.0124 0.357 Uiso 1 1 calc R U . . .
H29B H 0.6037 0.0886 0.9342 0.357 Uiso 1 1 calc R U . . .
H29C H 0.7126 0.1155 1.0066 0.357 Uiso 1 1 calc R U . . .
C28 C 0.8154(14) -0.0362(18) 1.0343(6) 0.334(12) Uani 1 1 d . . . . .
H28A H 0.8606 0.0259 1.0519 0.501 Uiso 1 1 calc R U . . .
H28B H 0.8677 -0.0927 1.0336 0.501 Uiso 1 1 calc R U . . .
H28C H 0.7716 -0.0529 1.0685 0.501 Uiso 1 1 calc R U . . .
H3A H 0.499(5) -0.179(5) 0.412(3) 0.095(19) Uiso 1 1 d . . . . .
H19 H 0.793(4) -0.025(3) 0.638(2) 0.043(13) Uiso 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 O1 2.066(3) . ?
Ru1 N1 2.078(3) . ?
Ru1 C1 2.146(5) . ?
Ru1 C6 2.151(5) . ?
Ru1 C4 2.182(4) . ?
Ru1 C2 2.182(5) . ?
Ru1 C5 2.195(5) . ?
Ru1 C3 2.203(4) . ?
Ru1 Cl2 2.4056(12) . ?
N1 C19 1.287(6) . ?
N1 N2 1.383(5) . ?
O1 C7 1.284(5) . ?
C7 N2 1.300(6) . ?
C7 C8 1.498(6) . ?
C1 C2 1.397(7) . ?
C1 C6 1.405(8) . ?
C4 C3 1.378(6) . ?
C4 C5 1.424(7) . ?
C3 C2 1.429(7) . ?
C5 C6 1.398(7) . ?
C5 C14 1.502(7) . ?
C2 C16 1.508(8) . ?
C8 C13 1.352(7) . ?
C8 C9 1.388(7) . ?
C10 C11 1.355(7) . ?
C10 C9 1.382(7) . ?
C13 C12 1.385(7) . ?
C11 O2 1.367(6) . ?
C11 C12 1.383(7) . ?
O2 C17 1.415(7) . ?
C16 C28 1.480(12) . ?
C16 C29 1.484(14) . ?
N3 C21 1.323(6) . ?
N3 C23 1.377(6) . ?
C19 C20 1.423(6) . ?
C20 C21 1.382(6) . ?
C20 C22 1.445(6) . ?
C23 C24 1.377(7) . ?
C23 C22 1.432(6) . ?
C22 C27 1.416(7) . ?
C27 C26 1.381(7) . ?
C24 C25 1.379(8) . ?
C26 C25 1.396(8) . ?

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 N1 75.60(13) . . ?
O1 Ru1 C1 105.42(19) . . ?
N1 Ru1 C1 104.49(17) . . ?
O1 Ru1 C6 139.37(18) . . ?
N1 Ru1 C6 94.48(16) . . ?
C1 Ru1 C6 38.2(2) . . ?
O1 Ru1 C4 137.04(16) . . ?
N1 Ru1 C4 145.93(18) . . ?
C1 Ru1 C4 79.01(19) . . ?
C6 Ru1 C4 67.01(19) . . ?
O1 Ru1 C2 89.53(16) . . ?
N1 Ru1 C2 133.91(17) . . ?
C1 Ru1 C2 37.64(19) . . ?
C6 Ru1 C2 69.02(19) . . ?
C4 Ru1 C2 67.85(19) . . ?
O1 Ru1 C5 171.80(15) . . ?
N1 Ru1 C5 110.87(17) . . ?
C1 Ru1 C5 68.5(2) . . ?
C6 Ru1 C5 37.51(19) . . ?
C4 Ru1 C5 37.97(18) . . ?
C2 Ru1 C5 82.33(19) . . ?
O1 Ru1 C3 104.63(16) . . ?
N1 Ru1 C3 171.48(16) . . ?
C1 Ru1 C3 67.13(18) . . ?
C6 Ru1 C3 79.78(18) . . ?
C4 Ru1 C3 36.64(17) . . ?
C2 Ru1 C3 38.04(19) . . ?
C5 Ru1 C3 68.19(19) . . ?
O1 Ru1 Cl2 86.91(10) . . ?
N1 Ru1 Cl2 83.78(11) . . ?
C1 Ru1 Cl2 166.44(15) . . ?
C6 Ru1 Cl2 131.82(16) . . ?
C4 Ru1 Cl2 88.13(13) . . ?
C2 Ru1 Cl2 139.59(14) . . ?
C5 Ru1 Cl2 98.63(14) . . ?
C3 Ru1 Cl2 104.74(13) . . ?
C19 N1 N2 116.3(4) . . ?
C19 N1 Ru1 127.6(3) . . ?
N2 N1 Ru1 115.8(3) . . ?
C7 O1 Ru1 112.7(3) . . ?
O1 C7 N2 125.3(4) . . ?
O1 C7 C8 116.7(4) . . ?
N2 C7 C8 117.9(4) . . ?
C2 C1 C6 122.4(5) . . ?
C2 C1 Ru1 72.6(3) . . ?
C6 C1 Ru1 71.1(3) . . ?
C3 C4 C5 123.2(5) . . ?
C3 C4 Ru1 72.5(3) . . ?
C5 C4 Ru1 71.5(3) . . ?
C4 C3 C2 120.4(4) . . ?
C4 C3 Ru1 70.9(3) . . ?
C2 C3 Ru1 70.2(3) . . ?
C6 C5 C4 115.9(5) . . ?
C6 C5 C14 122.3(5) . . ?
C4 C5 C14 121.8(5) . . ?
C6 C5 Ru1 69.5(3) . . ?
C4 C5 Ru1 70.5(3) . . ?
C14 C5 Ru1 129.3(3) . . ?
C5 C6 C1 121.4(5) . . ?
C5 C6 Ru1 73.0(3) . . ?
C1 C6 Ru1 70.7(3) . . ?
C1 C2 C3 116.7(5) . . ?
C1 C2 C16 119.3(6) . . ?
C3 C2 C16 124.0(5) . . ?
C1 C2 Ru1 69.8(3) . . ?
C3 C2 Ru1 71.8(3) . . ?
C16 C2 Ru1 127.3(4) . . ?
C7 N2 N1 110.6(3) . . ?
C13 C8 C9 117.7(5) . . ?
C13 C8 C7 122.1(4) . . ?
C9 C8 C7 120.1(4) . . ?
C11 C10 C9 120.6(5) . . ?
C10 C9 C8 120.5(5) . . ?
C8 C13 C12 122.8(5) . . ?
C10 C11 O2 116.5(5) . . ?
C10 C11 C12 120.0(5) . . ?
O2 C11 C12 123.5(5) . . ?
C11 C12 C13 118.4(5) . . ?
C11 O2 C17 118.0(5) . . ?
C28 C16 C29 94.7(11) . . ?
C28 C16 C2 106.2(7) . . ?
C29 C16 C2 113.8(8) . . ?
C21 N3 C23 110.7(4) . . ?
N1 C19 C20 129.7(5) . . ?
C21 C20 C19 130.8(5) . . ?
C21 C20 C22 105.7(4) . . ?
C19 C20 C22 123.4(4) . . ?
N3 C21 C20 110.8(4) . . ?
C24 C23 N3 130.9(5) . . ?
C24 C23 C22 122.7(5) . . ?
N3 C23 C22 106.4(4) . . ?
C27 C22 C23 118.0(5) . . ?
C27 C22 C20 135.7(4) . . ?
C23 C22 C20 106.3(4) . . ?
C26 C27 C22 118.5(5) . . ?
C23 C24 C25 117.6(5) . . ?
C27 C26 C25 121.5(6) . . ?
C24 C25 C26 121.6(5) . . ?

_refine_diff_density_max         1.305
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_cpx3
_database_code_depnum_ccdc_archive 'CCDC 1499166'
_audit_update_record             
;
2016-10-04 deposited with the CCDC.
2016-10-05 downloaded from the CCDC.
;
_audit_creation_date             2016-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H20 Cl N3 O2 Ru, H2 O'
_chemical_formula_sum            'C23 H22 Cl N3 O3 Ru'
_chemical_formula_weight         524.95
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7924(4)
_cell_length_b                   10.7114(4)
_cell_length_c                   26.6417(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.178(2)
_cell_angle_gamma                90
_cell_volume                     2223.25(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4448
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      52.424
_cell_measurement_theta_min      4.882
_shelx_estimated_absorpt_T_max   0.783
_shelx_estimated_absorpt_T_min   0.726
_exptl_absorpt_coefficient_mu    0.855
_exptl_absorpt_correction_T_max  0.7836
_exptl_absorpt_correction_T_min  0.7261
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            18187
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.289
_diffrn_reflns_theta_min         2.739
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4074
_reflns_number_total             5487
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.402
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5487
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+2.9582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1285
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1S(H1SA,H1SB)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C13(H13),
 C14(H14), C15(H15), C19(H19), C20(H20), C21(H21), C22(H22), N3(H3A), C23(H23)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.60727(4) 0.74188(3) 0.03079(2) 0.03137(11) Uani 1 1 d . . . . .
Cl1 Cl 0.31618(14) 0.82137(12) 0.02692(4) 0.0489(3) Uani 1 1 d . . . . .
O1 O 0.2871(5) 0.4345(3) 0.30246(11) 0.0586(9) Uani 1 1 d . . . . .
O1S O 0.5691(9) 0.2386(5) 0.3087(2) 0.114(2) Uani 1 1 d . . . . .
H1SA H 0.6139 0.2465 0.3378 0.171 Uiso 1 1 d G . . . .
H1SB H 0.4864 0.1869 0.3097 0.171 Uiso 1 1 d G . . . .
N1 N 0.6319(4) 0.8555(3) 0.09325(11) 0.0326(7) Uani 1 1 d . . . . .
N2 N 0.5796(5) 0.8041(3) 0.13841(11) 0.0381(8) Uani 1 1 d . . . . .
O2 O 0.5184(4) 0.6323(2) 0.08862(9) 0.0371(6) Uani 1 1 d . . . . .
C1 C 0.6268(10) 0.6243(8) -0.0362(3) 0.090(3) Uani 1 1 d . . . . .
H1 H 0.5515 0.5668 -0.0508 0.108 Uiso 1 1 calc R . . . .
C2 C 0.7443(15) 0.5878(6) -0.0016(4) 0.110(4) Uani 1 1 d . . . . .
H2 H 0.7447 0.5049 0.0088 0.133 Uiso 1 1 calc R . . . .
C3 C 0.8585(10) 0.6645(10) 0.0180(3) 0.098(3) Uani 1 1 d . . . . .
H3 H 0.9409 0.6339 0.0406 0.117 Uiso 1 1 calc R . . . .
C4 C 0.8589(7) 0.7849(8) 0.0063(2) 0.077(2) Uani 1 1 d . . . . .
H4 H 0.9397 0.8371 0.0216 0.092 Uiso 1 1 calc R . . . .
C5 C 0.7428(9) 0.8352(5) -0.0280(2) 0.0724(19) Uani 1 1 d . . . . .
H5 H 0.7451 0.9195 -0.0363 0.087 Uiso 1 1 calc R . . . .
C6 C 0.6196(8) 0.7532(9) -0.05016(18) 0.088(3) Uani 1 1 d . . . . .
H6 H 0.5371 0.7823 -0.0730 0.106 Uiso 1 1 calc R . . . .
C7 C 0.5216(5) 0.6889(3) 0.13131(13) 0.0324(8) Uani 1 1 d . . . . .
C8 C 0.4568(5) 0.6239(3) 0.17622(14) 0.0328(8) Uani 1 1 d . . . . .
C9 C 0.3789(6) 0.5068(4) 0.17281(15) 0.0462(11) Uani 1 1 d . . . . .
H9 H 0.3657 0.4683 0.1417 0.055 Uiso 1 1 calc R . . . .
C10 C 0.3215(6) 0.4476(4) 0.21521(16) 0.0505(12) Uani 1 1 d . . . . .
H10 H 0.2670 0.3706 0.2124 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3446(5) 0.5022(4) 0.26224(15) 0.0399(9) Uani 1 1 d . . . . .
C12 C 0.3059(7) 0.4898(5) 0.35148(17) 0.0665(15) Uani 1 1 d . . . . .
H12A H 0.4257 0.4997 0.3597 0.100 Uiso 1 1 calc GR . . . .
H12B H 0.2539 0.4366 0.3759 0.100 Uiso 1 1 calc GR . . . .
H12C H 0.2508 0.5699 0.3516 0.100 Uiso 1 1 calc GR . . . .
C13 C 0.4199(6) 0.6184(4) 0.26634(15) 0.0428(10) Uani 1 1 d . . . . .
H13 H 0.4337 0.6562 0.2976 0.051 Uiso 1 1 calc R . . . .
C14 C 0.4747(6) 0.6781(4) 0.22355(15) 0.0407(10) Uani 1 1 d . . . . .
H14 H 0.5249 0.7566 0.2264 0.049 Uiso 1 1 calc R . . . .
C15 C 0.6818(5) 0.9716(3) 0.09467(14) 0.0336(9) Uani 1 1 d . . . . .
H15 H 0.7222 1.0037 0.0647 0.040 Uiso 1 1 calc R . . . .
C16 C 0.6826(5) 1.0567(3) 0.13645(14) 0.0344(9) Uani 1 1 d . . . . .
C17 C 0.7559(5) 1.1811(4) 0.13486(15) 0.0364(9) Uani 1 1 d . . . . .
C18 C 0.7175(6) 1.2393(4) 0.18029(16) 0.0404(10) Uani 1 1 d . . . . .
C19 C 0.7728(7) 1.3607(4) 0.1917(2) 0.0557(13) Uani 1 1 d . . . . .
H19 H 0.7431 1.3996 0.2215 0.067 Uiso 1 1 calc R . . . .
C20 C 0.8720(7) 1.4196(5) 0.1574(2) 0.0658(15) Uani 1 1 d . . . . .
H20 H 0.9112 1.4999 0.1643 0.079 Uiso 1 1 calc R . . . .
C21 C 0.9168(7) 1.3631(4) 0.1120(2) 0.0614(14) Uani 1 1 d . . . . .
H21 H 0.9865 1.4053 0.0897 0.074 Uiso 1 1 calc R . . . .
C22 C 0.8573(6) 1.2443(4) 0.10022(18) 0.0452(10) Uani 1 1 d . . . . .
H22 H 0.8844 1.2072 0.0698 0.054 Uiso 1 1 calc R . . . .
N3 N 0.6263(5) 1.1562(3) 0.20841(13) 0.0466(9) Uani 1 1 d . . . . .
H3A H 0.5863 1.1712 0.2376 0.056 Uiso 1 1 calc R . . . .
C23 C 0.6087(6) 1.0469(4) 0.18311(15) 0.0445(10) Uani 1 1 d . . . . .
H23 H 0.5550 0.9759 0.1953 0.053 Uiso 1 1 calc R . . . .


_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 Cl1 2.4230(12) . ?
Ru1 N1 2.067(3) . ?
Ru1 O2 2.068(3) . ?
Ru1 C1 2.192(5) . ?
Ru1 C2 2.156(6) . ?
Ru1 C3 2.160(6) . ?
Ru1 C4 2.130(5) . ?
Ru1 C5 2.153(5) . ?
Ru1 C6 2.164(5) . ?
O1 C11 1.377(5) . ?
O1 C12 1.439(5) . ?
N1 N2 1.392(4) . ?
N1 C15 1.304(5) . ?
N2 C7 1.326(5) . ?
O2 C7 1.289(4) . ?
C1 C2 1.344(11) . ?
C1 C6 1.431(10) . ?
C2 C3 1.312(11) . ?
C3 C4 1.328(11) . ?
C4 C5 1.382(9) . ?
C5 C6 1.420(9) . ?
C7 C8 1.482(5) . ?
C8 C9 1.395(5) . ?
C8 C14 1.393(5) . ?
C9 C10 1.378(6) . ?
C10 C11 1.391(6) . ?
C11 C13 1.380(6) . ?
C13 C14 1.382(5) . ?
C15 C16 1.439(5) . ?
C16 C17 1.451(5) . ?
C16 C23 1.385(6) . ?
C17 C18 1.399(6) . ?
C17 C22 1.402(6) . ?
C18 C19 1.402(6) . ?
C18 N3 1.371(6) . ?
C19 C20 1.364(7) . ?
C20 C21 1.403(8) . ?
C21 C22 1.387(6) . ?
N3 C23 1.356(5) . ?

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 Cl1 84.19(10) . . ?
N1 Ru1 O2 76.19(11) . . ?
N1 Ru1 C1 170.6(2) . . ?
N1 Ru1 C2 137.3(4) . . ?
N1 Ru1 C3 106.5(3) . . ?
N1 Ru1 C4 92.79(18) . . ?
N1 Ru1 C5 105.90(19) . . ?
N1 Ru1 C6 139.8(3) . . ?
O2 Ru1 Cl1 84.47(9) . . ?
O2 Ru1 C1 108.1(2) . . ?
O2 Ru1 C2 92.3(2) . . ?
O2 Ru1 C3 102.6(2) . . ?
O2 Ru1 C4 132.5(3) . . ?
O2 Ru1 C5 169.3(2) . . ?
O2 Ru1 C6 142.8(3) . . ?
C1 Ru1 Cl1 104.4(3) . . ?
C2 Ru1 Cl1 136.3(4) . . ?
C2 Ru1 C1 36.0(3) . . ?
C2 Ru1 C3 35.4(3) . . ?
C2 Ru1 C6 67.1(3) . . ?
C3 Ru1 Cl1 168.3(2) . . ?
C3 Ru1 C1 64.7(3) . . ?
C3 Ru1 C6 78.8(2) . . ?
C4 Ru1 Cl1 141.1(3) . . ?
C4 Ru1 C1 78.2(2) . . ?
C4 Ru1 C2 64.9(3) . . ?
C4 Ru1 C3 36.1(3) . . ?
C4 Ru1 C5 37.6(3) . . ?
C4 Ru1 C6 67.8(2) . . ?
C5 Ru1 Cl1 106.17(19) . . ?
C5 Ru1 C1 68.3(2) . . ?
C5 Ru1 C2 79.0(2) . . ?
C5 Ru1 C3 66.7(3) . . ?
C5 Ru1 C6 38.4(3) . . ?
C6 Ru1 Cl1 89.93(15) . . ?
C6 Ru1 C1 38.3(3) . . ?
C11 O1 C12 117.4(4) . . ?
N2 N1 Ru1 116.1(2) . . ?
C15 N1 Ru1 127.4(3) . . ?
C15 N1 N2 116.4(3) . . ?
C7 N2 N1 110.5(3) . . ?
C7 O2 Ru1 112.9(2) . . ?
C2 C1 Ru1 70.6(4) . . ?
C2 C1 C6 118.8(6) . . ?
C6 C1 Ru1 69.8(3) . . ?
C1 C2 Ru1 73.5(4) . . ?
C3 C2 Ru1 72.5(4) . . ?
C3 C2 C1 122.5(7) . . ?
C2 C3 Ru1 72.2(4) . . ?
C2 C3 C4 121.3(7) . . ?
C4 C3 Ru1 70.7(4) . . ?
C3 C4 Ru1 73.2(4) . . ?
C3 C4 C5 122.0(6) . . ?
C5 C4 Ru1 72.1(3) . . ?
C4 C5 Ru1 70.3(3) . . ?
C4 C5 C6 117.5(5) . . ?
C6 C5 Ru1 71.2(3) . . ?
C1 C6 Ru1 71.9(3) . . ?
C5 C6 Ru1 70.4(3) . . ?
C5 C6 C1 117.8(5) . . ?
N2 C7 C8 116.3(3) . . ?
O2 C7 N2 124.3(3) . . ?
O2 C7 C8 119.4(3) . . ?
C9 C8 C7 121.7(3) . . ?
C14 C8 C7 120.3(3) . . ?
C14 C8 C9 118.0(4) . . ?
C10 C9 C8 120.5(4) . . ?
C9 C10 C11 120.5(4) . . ?
O1 C11 C10 116.2(4) . . ?
O1 C11 C13 124.0(4) . . ?
C13 C11 C10 119.8(4) . . ?
C11 C13 C14 119.4(4) . . ?
C13 C14 C8 121.8(4) . . ?
N1 C15 C16 128.6(4) . . ?
C15 C16 C17 123.7(4) . . ?
C23 C16 C15 130.6(4) . . ?
C23 C16 C17 105.5(3) . . ?
C18 C17 C16 107.0(4) . . ?
C18 C17 C22 119.2(4) . . ?
C22 C17 C16 133.7(4) . . ?
C17 C18 C19 122.1(4) . . ?
N3 C18 C17 107.8(3) . . ?
N3 C18 C19 130.1(4) . . ?
C20 C19 C18 117.3(5) . . ?
C19 C20 C21 122.2(4) . . ?
C22 C21 C20 120.2(5) . . ?
C21 C22 C17 119.0(5) . . ?
C23 N3 C18 109.7(4) . . ?
N3 C23 C16 110.0(4) . . ?

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 N1 N2 C7 -0.5(4) . . . . ?
Ru1 N1 C15 C16 172.6(3) . . . . ?
Ru1 O2 C7 N2 -1.8(5) . . . . ?
Ru1 O2 C7 C8 178.1(3) . . . . ?
Ru1 C1 C2 C3 -55.8(6) . . . . ?
Ru1 C1 C6 C5 55.1(4) . . . . ?
Ru1 C2 C3 C4 -53.1(6) . . . . ?
Ru1 C3 C4 C5 -55.4(5) . . . . ?
Ru1 C4 C5 C6 -55.1(4) . . . . ?
Ru1 C5 C6 C1 -55.9(4) . . . . ?
O1 C11 C13 C14 179.4(4) . . . . ?
N1 N2 C7 O2 1.5(6) . . . . ?
N1 N2 C7 C8 -178.4(3) . . . . ?
N1 C15 C16 C17 174.2(4) . . . . ?
N1 C15 C16 C23 -11.3(7) . . . . ?
N2 N1 C15 C16 -3.3(6) . . . . ?
N2 C7 C8 C9 174.4(4) . . . . ?
N2 C7 C8 C14 -6.6(6) . . . . ?
O2 C7 C8 C9 -5.5(6) . . . . ?
O2 C7 C8 C14 173.5(4) . . . . ?
C1 C2 C3 Ru1 56.2(6) . . . . ?
C1 C2 C3 C4 3.2(11) . . . . ?
C2 C1 C6 Ru1 -52.6(5) . . . . ?
C2 C1 C6 C5 2.5(8) . . . . ?
C2 C3 C4 Ru1 53.7(6) . . . . ?
C2 C3 C4 C5 -1.8(10) . . . . ?
C3 C4 C5 Ru1 56.0(5) . . . . ?
C3 C4 C5 C6 0.9(8) . . . . ?
C4 C5 C6 Ru1 54.6(4) . . . . ?
C4 C5 C6 C1 -1.3(7) . . . . ?
C6 C1 C2 Ru1 52.2(5) . . . . ?
C6 C1 C2 C3 -3.5(10) . . . . ?
C7 C8 C9 C10 179.3(4) . . . . ?
C7 C8 C14 C13 -178.2(4) . . . . ?
C8 C9 C10 C11 -1.8(8) . . . . ?
C9 C8 C14 C13 0.9(7) . . . . ?
C9 C10 C11 O1 -178.3(4) . . . . ?
C9 C10 C11 C13 2.3(7) . . . . ?
C10 C11 C13 C14 -1.3(7) . . . . ?
C11 C13 C14 C8 -0.3(7) . . . . ?
C12 O1 C11 C10 -178.7(5) . . . . ?
C12 O1 C11 C13 0.6(7) . . . . ?
C14 C8 C9 C10 0.2(7) . . . . ?
C15 N1 N2 C7 175.9(4) . . . . ?
C15 C16 C17 C18 174.3(4) . . . . ?
C15 C16 C17 C22 -9.8(7) . . . . ?
C15 C16 C23 N3 -173.0(4) . . . . ?
C16 C17 C18 C19 178.6(4) . . . . ?
C16 C17 C18 N3 0.1(5) . . . . ?
C16 C17 C22 C21 -175.6(5) . . . . ?
C17 C16 C23 N3 2.3(5) . . . . ?
C17 C18 C19 C20 -2.3(7) . . . . ?
C17 C18 N3 C23 1.4(5) . . . . ?
C18 C17 C22 C21 -0.1(6) . . . . ?
C18 C19 C20 C21 0.6(8) . . . . ?
C18 N3 C23 C16 -2.3(5) . . . . ?
C19 C18 N3 C23 -177.1(4) . . . . ?
C19 C20 C21 C22 1.3(8) . . . . ?
C20 C21 C22 C17 -1.6(7) . . . . ?
C22 C17 C18 C19 2.0(6) . . . . ?
C22 C17 C18 N3 -176.5(4) . . . . ?
N3 C18 C19 C20 175.9(5) . . . . ?
C23 C16 C17 C18 -1.4(4) . . . . ?
C23 C16 C17 C22 174.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
