# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

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

data_kjben
_database_code_depnum_ccdc_archive 'CCDC 1443341'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_audit_creation_date             2015-04-27
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H12 N2 O S2'
_chemical_formula_sum            'C13 H12 N2 O S2'
_chemical_formula_weight         276.37
_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'
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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0928(13)
_cell_length_b                   8.8375(19)
_cell_length_c                   12.646(3)
_cell_angle_alpha                89.795(2)
_cell_angle_beta                 84.279(2)
_cell_angle_gamma                71.621(2)
_cell_volume                     642.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5331
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.468
_cell_measurement_theta_min      2.880
_shelx_estimated_absorpt_T_max   0.830
_shelx_estimated_absorpt_T_min   0.803
_exptl_absorpt_coefficient_mu    0.402
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5125
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1246 before and 0.0400 after correction.
The Ratio of minimum to maximum transmission is 0.6874.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.48
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7387
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.430
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2683
_reflns_number_total             2887
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2887
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0412P)²+0.3148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0863
_refine_ls_wR_factor_ref         0.0873
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12),
 C13(H13)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.98630(6) -0.02257(4) 0.32609(3) 0.02037(11) Uani 1 1 d . . . . .
S2 S 0.18562(6) 0.47306(5) 0.66111(3) 0.02670(12) Uani 1 1 d . . . . .
O1 O 0.25588(17) 0.24561(12) 0.47939(8) 0.0209(2) Uani 1 1 d . . . . .
N1 N 0.52690(19) 0.04546(13) 0.32617(9) 0.0158(2) Uani 1 1 d . . . . .
H1 H 0.3869 0.0841 0.3603 0.019 Uiso 1 1 calc R . . . .
N2 N 0.6544(2) 0.15244(14) 0.46590(9) 0.0171(2) Uani 1 1 d . . . . .
H2 H 0.7730 0.1489 0.5013 0.021 Uiso 1 1 calc R . . . .
C1 C 0.5095(2) 0.08979(16) 0.13454(10) 0.0175(3) Uani 1 1 d . . . . .
C2 C 0.2844(3) 0.18313(18) 0.12062(13) 0.0264(3) Uani 1 1 d . . . . .
H2A H 0.1570 0.1687 0.1645 0.032 Uiso 1 1 calc R . . . .
C3 C 0.2439(4) 0.2978(2) 0.04292(15) 0.0371(4) Uani 1 1 d . . . . .
H3 H 0.0894 0.3616 0.0342 0.044 Uiso 1 1 calc R . . . .
C4 C 0.4279(4) 0.3188(2) -0.02141(13) 0.0387(4) Uani 1 1 d . . . . .
H4 H 0.4001 0.3971 -0.0744 0.046 Uiso 1 1 calc R . . . .
C5 C 0.6517(4) 0.2263(2) -0.00887(13) 0.0382(4) Uani 1 1 d . . . . .
H5 H 0.7781 0.2405 -0.0536 0.046 Uiso 1 1 calc R . . . .
C6 C 0.6942(3) 0.1113(2) 0.06963(12) 0.0266(3) Uani 1 1 d . . . . .
H6 H 0.8491 0.0482 0.0784 0.032 Uiso 1 1 calc R . . . .
C7 C 0.5506(2) -0.03213(16) 0.22117(10) 0.0166(3) Uani 1 1 d . . . . .
H7A H 0.4369 -0.0912 0.2208 0.020 Uiso 1 1 calc R . . . .
H7B H 0.7086 -0.1098 0.2069 0.020 Uiso 1 1 calc R . . . .
C8 C 0.7059(2) 0.06029(15) 0.37225(10) 0.0152(3) Uani 1 1 d . . . . .
C9 C 0.4389(2) 0.24892(15) 0.50991(10) 0.0157(3) Uani 1 1 d . . . . .
C10 C 0.4459(2) 0.35923(15) 0.59534(10) 0.0154(3) Uani 1 1 d . . . . .
C11 C 0.6297(2) 0.39801(16) 0.62918(11) 0.0193(3) Uani 1 1 d . . . . .
H11 H 0.7873 0.3490 0.6017 0.023 Uiso 1 1 calc R . . . .
C12 C 0.5564(3) 0.51987(17) 0.71006(12) 0.0233(3) Uani 1 1 d . . . . .
H12 H 0.6596 0.5611 0.7433 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3221(3) 0.57076(17) 0.73446(12) 0.0254(3) Uani 1 1 d . . . . .
H13 H 0.2430 0.6518 0.7866 0.030 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
S1 C8 1.6767(14) . ?
S2 C10 1.7190(14) . ?
S2 C13 1.7059(16) . ?
O1 C9 1.2247(17) . ?
N1 H1 0.8800 . ?
N1 C7 1.4697(17) . ?
N1 C8 1.3279(18) . ?
N2 H2 0.8800 . ?
N2 C8 1.3913(17) . ?
N2 C9 1.3828(17) . ?
C1 C2 1.388(2) . ?
C1 C6 1.388(2) . ?
C1 C7 1.5165(18) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.4704(18) . ?
C10 C11 1.3761(19) . ?
C11 H11 0.9500 . ?
C11 C12 1.421(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.358(2) . ?
C13 H13 0.9500 . ?

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
C13 S2 C10 91.60(7) . . ?
C7 N1 H1 118.3 . . ?
C8 N1 H1 118.3 . . ?
C8 N1 C7 123.40(11) . . ?
C8 N2 H2 116.1 . . ?
C9 N2 H2 116.1 . . ?
C9 N2 C8 127.71(11) . . ?
C2 C1 C6 119.27(14) . . ?
C2 C1 C7 119.75(13) . . ?
C6 C1 C7 120.98(13) . . ?
C1 C2 H2A 119.8 . . ?
C1 C2 C3 120.48(16) . . ?
C3 C2 H2A 119.8 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.07(17) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.02(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.31(17) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 119.85(16) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N1 C7 C1 110.97(11) . . ?
N1 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C1 C7 H7A 109.4 . . ?
C1 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 S1 125.08(10) . . ?
N1 C8 N2 116.85(12) . . ?
N2 C8 S1 118.06(10) . . ?
O1 C9 N2 123.07(12) . . ?
O1 C9 C10 122.18(12) . . ?
N2 C9 C10 114.74(11) . . ?
C9 C10 S2 117.77(10) . . ?
C11 C10 S2 111.41(10) . . ?
C11 C10 C9 130.64(12) . . ?
C10 C11 H11 123.9 . . ?
C10 C11 C12 112.13(13) . . ?
C12 C11 H11 123.9 . . ?
C11 C12 H12 123.8 . . ?
C13 C12 C11 112.34(13) . . ?
C13 C12 H12 123.8 . . ?
S2 C13 H13 123.7 . . ?
C12 C13 S2 112.52(11) . . ?
C12 C13 H13 123.7 . . ?

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 S1 0.88 2.95 3.5299(14) 125.2 1_455
N1 H1 O1 0.88 2.00 2.6748(15) 132.5 .
N2 H2 S1 0.88 2.78 3.5456(13) 145.7 2_756

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
S2 C10 C11 C12 0.73(15) . . . . ?
O1 C9 C10 S2 5.93(17) . . . . ?
O1 C9 C10 C11 -168.76(14) . . . . ?
N2 C9 C10 S2 -175.29(9) . . . . ?
N2 C9 C10 C11 10.0(2) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C1 C7 N1 -76.63(16) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C1 C7 N1 102.44(15) . . . . ?
C7 N1 C8 S1 -7.01(18) . . . . ?
C7 N1 C8 N2 172.79(11) . . . . ?
C7 C1 C2 C3 178.71(14) . . . . ?
C7 C1 C6 C5 -179.11(13) . . . . ?
C8 N1 C7 C1 -95.31(15) . . . . ?
C8 N2 C9 O1 12.3(2) . . . . ?
C8 N2 C9 C10 -166.49(12) . . . . ?
C9 N2 C8 S1 170.15(10) . . . . ?
C9 N2 C8 N1 -9.7(2) . . . . ?
C9 C10 C11 C12 175.69(13) . . . . ?
C10 S2 C13 C12 0.22(12) . . . . ?
C10 C11 C12 C13 -0.57(18) . . . . ?
C11 C12 C13 S2 0.15(17) . . . . ?
C13 S2 C10 C9 -176.23(11) . . . . ?
C13 S2 C10 C11 -0.55(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ruc5
_database_code_depnum_ccdc_archive 'CCDC 1443342'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_audit_creation_date             2014-07-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H24 Cl2 N2 O Ru S2'
_chemical_formula_sum            'C22 H24 Cl2 N2 O Ru S2'
_chemical_formula_weight         568.52
_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'
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'
S S 0.1246 0.1234 '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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.611(3)
_cell_length_b                   12.309(4)
_cell_length_c                   18.406(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.816(3)
_cell_angle_gamma                90
_cell_volume                     2361.4(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9634
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.374
_cell_measurement_theta_min      2.253
_shelx_estimated_absorpt_T_max   0.744
_shelx_estimated_absorpt_T_min   0.592
_exptl_absorpt_coefficient_mu    1.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0942 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.6290.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26452
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.453
_diffrn_reflns_theta_min         1.954
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4815
_reflns_number_total             5372
_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        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.072
_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)+(0.0238P)²+1.9972P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0612
_refine_ls_wR_factor_ref         0.0631
_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
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12), C14(H14), C15(H15), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_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 0.49335(2) 0.48682(2) 0.28522(2) 0.00920(6) Uani 1 1 d . . . . .
Cl1 Cl 0.30691(5) 0.54696(4) 0.19694(3) 0.01485(11) Uani 1 1 d . . . . .
Cl2 Cl 0.45270(5) 0.63579(4) 0.36289(3) 0.01388(11) Uani 1 1 d . . . . .
S1 S 0.36369(5) 0.36519(4) 0.34290(3) 0.01496(12) Uani 1 1 d . . . . .
S2 S -0.07479(6) 0.74785(5) 0.34908(4) 0.02214(14) Uani 1 1 d . . . . .
O1 O -0.00305(16) 0.52297(14) 0.38587(10) 0.0229(4) Uani 1 1 d . . . . .
N1 N 0.18280(17) 0.51705(14) 0.33950(11) 0.0133(4) Uani 1 1 d . . . . .
H1 H 0.2295 0.5537 0.3132 0.016 Uiso 1 1 calc R U . . .
N2 N 0.15101(18) 0.35669(15) 0.39733(11) 0.0162(4) Uani 1 1 d . . . . .
H2 H 0.0759 0.3850 0.4000 0.019 Uiso 1 1 calc R U . . .
C1 C 0.2248(2) 0.41486(18) 0.36190(12) 0.0127(4) Uani 1 1 d . . . . .
C2 C 0.0742(2) 0.56820(18) 0.35427(13) 0.0149(4) Uani 1 1 d . . . . .
C3 C 0.0562(2) 0.68047(18) 0.32889(12) 0.0132(4) Uani 1 1 d . . . . .
C4 C 0.1262(2) 0.74560(19) 0.29142(13) 0.0181(5) Uani 1 1 d . . . . .
H4 H 0.2025 0.7229 0.2759 0.022 Uiso 1 1 calc R U . . .
C5 C 0.0728(2) 0.8503(2) 0.27827(14) 0.0226(5) Uani 1 1 d . . . . .
H5 H 0.1087 0.9060 0.2528 0.027 Uiso 1 1 calc R U . . .
C6 C -0.0364(2) 0.86211(19) 0.30646(14) 0.0201(5) Uani 1 1 d . . . . .
H6 H -0.0856 0.9271 0.3027 0.024 Uiso 1 1 calc R U . . .
C7 C 0.1787(2) 0.25286(18) 0.43201(12) 0.0135(4) Uani 1 1 d . . . . .
C8 C 0.2690(2) 0.24433(19) 0.49628(13) 0.0172(5) Uani 1 1 d . . . . .
H8 H 0.3224 0.3042 0.5140 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2802(2) 0.1470(2) 0.53455(13) 0.0204(5) Uani 1 1 d . . . . .
H9 H 0.3415 0.1405 0.5792 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2041(2) 0.0596(2) 0.50894(14) 0.0222(5) Uani 1 1 d . . . . .
H10 H 0.2121 -0.0065 0.5361 0.027 Uiso 1 1 calc R U . . .
C11 C 0.1160(2) 0.0681(2) 0.44374(14) 0.0222(5) Uani 1 1 d . . . . .
H11 H 0.0638 0.0076 0.4256 0.027 Uiso 1 1 calc R U . . .
C12 C 0.1037(2) 0.16499(19) 0.40472(13) 0.0180(5) Uani 1 1 d . . . . .
H12 H 0.0440 0.1709 0.3595 0.022 Uiso 1 1 calc R U . . .
C13 C 0.6661(2) 0.40296(18) 0.34033(12) 0.0132(4) Uani 1 1 d . . . . .
C14 C 0.6938(2) 0.51295(18) 0.32943(13) 0.0149(5) Uani 1 1 d . . . . .
H14 H 0.7324 0.5555 0.3707 0.018 Uiso 1 1 calc R U . . .
C15 C 0.6657(2) 0.56232(18) 0.25829(13) 0.0151(5) Uani 1 1 d . . . . .
H15 H 0.6867 0.6365 0.2528 0.018 Uiso 1 1 calc R U . . .
C16 C 0.6070(2) 0.50202(18) 0.19590(13) 0.0149(5) Uani 1 1 d . . . . .
C17 C 0.5776(2) 0.39093(18) 0.20652(12) 0.0141(4) Uani 1 1 d . . . . .
H17 H 0.5377 0.3487 0.1654 0.017 Uiso 1 1 calc R U . . .
C18 C 0.6066(2) 0.34271(18) 0.27701(13) 0.0139(4) Uani 1 1 d . . . . .
H18 H 0.5861 0.2684 0.2825 0.017 Uiso 1 1 calc R U . . .
C19 C 0.6908(2) 0.34946(19) 0.41571(13) 0.0174(5) Uani 1 1 d . . . . .
H19 H 0.6201 0.2961 0.4167 0.021 Uiso 1 1 calc R U . . .
C20 C 0.8166(2) 0.2858(2) 0.42643(14) 0.0234(5) Uani 1 1 d . . . . .
H20A H 0.8150 0.2359 0.3848 0.035 Uiso 1 1 calc R U . . .
H20B H 0.8270 0.2442 0.4726 0.035 Uiso 1 1 calc R U . . .
H20C H 0.8886 0.3364 0.4288 0.035 Uiso 1 1 calc R U . . .
C21 C 0.6904(3) 0.4290(2) 0.47850(14) 0.0294(6) Uani 1 1 d . . . . .
H21A H 0.7650 0.4770 0.4828 0.044 Uiso 1 1 calc R U . . .
H21B H 0.6941 0.3889 0.5249 0.044 Uiso 1 1 calc R U . . .
H21C H 0.6116 0.4725 0.4684 0.044 Uiso 1 1 calc R U . . .
C22 C 0.5713(2) 0.5529(2) 0.12121(13) 0.0202(5) Uani 1 1 d . . . . .
H22A H 0.4832 0.5325 0.0991 0.030 Uiso 1 1 calc R U . . .
H22B H 0.6299 0.5274 0.0896 0.030 Uiso 1 1 calc R U . . .
H22C H 0.5773 0.6321 0.1260 0.030 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 Cl1 2.4280(8) . ?
Ru1 Cl2 2.4132(8) . ?
Ru1 S1 2.4104(7) . ?
Ru1 C13 2.181(2) . ?
Ru1 C14 2.154(2) . ?
Ru1 C15 2.190(2) . ?
Ru1 C16 2.222(2) . ?
Ru1 C17 2.185(2) . ?
Ru1 C18 2.164(2) . ?
S1 C1 1.691(2) . ?
S2 C3 1.719(2) . ?
S2 C6 1.697(3) . ?
O1 C2 1.224(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.372(3) . ?
N1 C2 1.385(3) . ?
N2 H2 0.8800 . ?
N2 C1 1.320(3) . ?
N2 C7 1.434(3) . ?
C2 C3 1.460(3) . ?
C3 C4 1.364(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.410(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 C12 1.381(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.408(3) . ?
C13 C18 1.425(3) . ?
C13 C19 1.513(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.423(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.410(3) . ?
C16 C17 1.424(3) . ?
C16 C22 1.493(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.407(3) . ?
C18 H18 0.9500 . ?
C19 H19 1.0000 . ?
C19 C20 1.529(3) . ?
C19 C21 1.515(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
Cl2 Ru1 Cl1 87.19(3) . . ?
S1 Ru1 Cl1 91.34(3) . . ?
S1 Ru1 Cl2 91.76(3) . . ?
C13 Ru1 Cl1 164.52(6) . . ?
C13 Ru1 Cl2 108.19(6) . . ?
C13 Ru1 S1 90.03(6) . . ?
C13 Ru1 C15 68.98(9) . . ?
C13 Ru1 C16 81.86(8) . . ?
C13 Ru1 C17 68.91(8) . . ?
C14 Ru1 Cl1 146.10(6) . . ?
C14 Ru1 Cl2 86.35(6) . . ?
C14 Ru1 S1 122.08(7) . . ?
C14 Ru1 C13 37.89(8) . . ?
C14 Ru1 C15 38.24(9) . . ?
C14 Ru1 C16 68.42(9) . . ?
C14 Ru1 C17 80.41(8) . . ?
C14 Ru1 C18 68.09(8) . . ?
C15 Ru1 Cl1 109.24(7) . . ?
C15 Ru1 Cl2 93.52(6) . . ?
C15 Ru1 S1 158.96(6) . . ?
C15 Ru1 C16 37.28(8) . . ?
C16 Ru1 Cl1 88.09(7) . . ?
C16 Ru1 Cl2 123.82(6) . . ?
C16 Ru1 S1 144.31(6) . . ?
C17 Ru1 Cl1 95.99(6) . . ?
C17 Ru1 Cl2 160.71(6) . . ?
C17 Ru1 S1 107.14(6) . . ?
C17 Ru1 C15 67.44(8) . . ?
C17 Ru1 C16 37.70(8) . . ?
C18 Ru1 Cl1 126.63(6) . . ?
C18 Ru1 Cl2 145.86(6) . . ?
C18 Ru1 S1 83.80(6) . . ?
C18 Ru1 C13 38.30(8) . . ?
C18 Ru1 C15 80.43(8) . . ?
C18 Ru1 C16 68.38(8) . . ?
C18 Ru1 C17 37.76(8) . . ?
C1 S1 Ru1 117.26(8) . . ?
C6 S2 C3 91.49(12) . . ?
C1 N1 H1 116.8 . . ?
C1 N1 C2 126.42(19) . . ?
C2 N1 H1 116.8 . . ?
C1 N2 H2 116.1 . . ?
C1 N2 C7 127.73(19) . . ?
C7 N2 H2 116.1 . . ?
N1 C1 S1 121.07(16) . . ?
N2 C1 S1 121.79(17) . . ?
N2 C1 N1 117.13(19) . . ?
O1 C2 N1 122.9(2) . . ?
O1 C2 C3 121.6(2) . . ?
N1 C2 C3 115.52(19) . . ?
C2 C3 S2 116.73(16) . . ?
C4 C3 S2 111.39(17) . . ?
C4 C3 C2 131.9(2) . . ?
C3 C4 H4 123.7 . . ?
C3 C4 C5 112.6(2) . . ?
C5 C4 H4 123.7 . . ?
C4 C5 H5 124.0 . . ?
C6 C5 C4 112.0(2) . . ?
C6 C5 H5 124.0 . . ?
S2 C6 H6 123.8 . . ?
C5 C6 S2 112.48(18) . . ?
C5 C6 H6 123.8 . . ?
C8 C7 N2 120.1(2) . . ?
C8 C7 C12 120.8(2) . . ?
C12 C7 N2 118.7(2) . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.8(2) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.9(2) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 C11 119.6(2) . . ?
C7 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 Ru1 70.03(12) . . ?
C14 C13 C18 117.1(2) . . ?
C14 C13 C19 123.0(2) . . ?
C18 C13 Ru1 70.20(12) . . ?
C18 C13 C19 119.8(2) . . ?
C19 C13 Ru1 128.20(15) . . ?
Ru1 C14 H14 129.1 . . ?
C13 C14 Ru1 72.08(12) . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.9(2) . . ?
C15 C14 Ru1 72.23(13) . . ?
C15 C14 H14 119.1 . . ?
Ru1 C15 H15 130.9 . . ?
C14 C15 Ru1 69.52(12) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 Ru1 72.60(12) . . ?
C16 C15 C14 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 Ru1 70.12(13) . . ?
C15 C16 C17 117.9(2) . . ?
C15 C16 C22 121.7(2) . . ?
C17 C16 Ru1 69.75(12) . . ?
C17 C16 C22 120.3(2) . . ?
C22 C16 Ru1 129.56(16) . . ?
Ru1 C17 H17 130.4 . . ?
C16 C17 Ru1 72.55(12) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 Ru1 70.29(12) . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
Ru1 C18 H18 129.8 . . ?
C13 C18 Ru1 71.51(12) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 Ru1 71.96(12) . . ?
C17 C18 C13 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C13 C19 H19 107.5 . . ?
C13 C19 C20 109.79(19) . . ?
C13 C19 C21 113.2(2) . . ?
C20 C19 H19 107.5 . . ?
C21 C19 H19 107.5 . . ?
C21 C19 C20 111.1(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C16 C22 H22A 109.5 . . ?
C16 C22 H22B 109.5 . . ?
C16 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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 Cl1 0.88 2.43 3.171(2) 141.7 .
N1 H1 Cl2 0.88 2.58 3.172(2) 125.4 .
N2 H2 O1 0.88 1.89 2.603(3) 137.0 .

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 S1 C1 N1 5.5(2) . . . . ?
Ru1 S1 C1 N2 -175.94(16) . . . . ?
Ru1 C13 C14 C15 -54.62(18) . . . . ?
Ru1 C13 C18 C17 54.06(18) . . . . ?
Ru1 C13 C19 C20 171.21(17) . . . . ?
Ru1 C13 C19 C21 -64.0(3) . . . . ?
Ru1 C14 C15 C16 -53.76(18) . . . . ?
Ru1 C15 C16 C17 -52.55(17) . . . . ?
Ru1 C15 C16 C22 124.9(2) . . . . ?
Ru1 C16 C17 C18 -52.99(18) . . . . ?
Ru1 C17 C18 C13 -53.85(18) . . . . ?
S2 C3 C4 C5 -0.6(3) . . . . ?
O1 C2 C3 S2 2.7(3) . . . . ?
O1 C2 C3 C4 -178.0(3) . . . . ?
N1 C2 C3 S2 -177.88(16) . . . . ?
N1 C2 C3 C4 1.4(4) . . . . ?
N2 C7 C8 C9 170.4(2) . . . . ?
N2 C7 C12 C11 -170.4(2) . . . . ?
C1 N1 C2 O1 -5.2(4) . . . . ?
C1 N1 C2 C3 175.4(2) . . . . ?
C1 N2 C7 C8 71.0(3) . . . . ?
C1 N2 C7 C12 -116.2(3) . . . . ?
C2 N1 C1 S1 -177.13(18) . . . . ?
C2 N1 C1 N2 4.2(3) . . . . ?
C2 C3 C4 C5 -179.9(2) . . . . ?
C3 S2 C6 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 S2 0.3(3) . . . . ?
C6 S2 C3 C2 -179.94(19) . . . . ?
C6 S2 C3 C4 0.64(19) . . . . ?
C7 N2 C1 S1 7.6(3) . . . . ?
C7 N2 C1 N1 -173.7(2) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C7 C12 C11 2.3(3) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C12 C7 C8 C9 -2.2(3) . . . . ?
C13 C14 C15 Ru1 54.55(18) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C13 C18 Ru1 -53.66(17) . . . . ?
C14 C13 C18 C17 0.4(3) . . . . ?
C14 C13 C19 C20 -99.2(2) . . . . ?
C14 C13 C19 C21 25.6(3) . . . . ?
C14 C15 C16 Ru1 52.35(18) . . . . ?
C14 C15 C16 C17 -0.2(3) . . . . ?
C14 C15 C16 C22 177.3(2) . . . . ?
C15 C16 C17 Ru1 52.72(17) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 Ru1 54.02(18) . . . . ?
C16 C17 C18 C13 0.2(3) . . . . ?
C18 C13 C14 Ru1 53.74(17) . . . . ?
C18 C13 C14 C15 -0.9(3) . . . . ?
C18 C13 C19 C20 83.8(2) . . . . ?
C18 C13 C19 C21 -151.4(2) . . . . ?
C19 C13 C14 Ru1 -123.3(2) . . . . ?
C19 C13 C14 C15 -177.9(2) . . . . ?
C19 C13 C18 Ru1 123.45(19) . . . . ?
C19 C13 C18 C17 177.51(19) . . . . ?
C22 C16 C17 Ru1 -124.8(2) . . . . ?
C22 C16 C17 C18 -177.8(2) . . . . ?

####################################################################### 
# 
# 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_kjrutuben
_database_code_depnum_ccdc_archive 'CCDC 1443343'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_audit_creation_date             2015-04-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H26 Cl2 N2 O Ru S2'
_chemical_formula_sum            'C23 H26 Cl2 N2 O Ru S2'
_chemical_formula_weight         582.55
_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'
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'
S S 0.1246 0.1234 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3715(14)
_cell_length_b                   11.0452(16)
_cell_length_c                   12.0454(17)
_cell_angle_alpha                76.0930(10)
_cell_angle_beta                 80.9680(10)
_cell_angle_gamma                83.2620(10)
_cell_volume                     1191.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.501
_cell_measurement_theta_min      2.208
_shelx_estimated_absorpt_T_max   0.753
_shelx_estimated_absorpt_T_min   0.579
_exptl_absorpt_coefficient_mu    1.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1084 before and 0.0404 after correction.
The Ratio of minimum to maximum transmission is 0.6592.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.56
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13903
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.501
_diffrn_reflns_theta_min         2.208
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5130
_reflns_number_total             5397
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0248
_refine_ls_R_factor_gt           0.0230
_refine_ls_restrained_S_all      1.122
_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)+(0.0195P)²+0.7743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0554
_refine_ls_wR_factor_ref         0.0562
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C19(H19), C11(H11), C15(H15), C4(H4), C6(H6), C16(H16),
 C5(H5), C18(H18), C8(H8), C7(H7), C13(H13), C12(H12)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_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 0.75138(2) 0.66173(2) 0.53625(2) 0.00739(5) Uani 1 1 d . . . . .
Cl2 Cl 0.73863(5) 0.44276(4) 0.63682(4) 0.01112(9) Uani 1 1 d . . . . .
Cl1 Cl 0.92719(5) 0.68014(4) 0.65890(4) 0.01301(9) Uani 1 1 d . . . . .
S1 S 0.56056(5) 0.73006(4) 0.67188(4) 0.01135(9) Uani 1 1 d . . . . .
S2 S 0.88470(5) 0.38073(4) 1.10588(4) 0.01450(10) Uani 1 1 d . . . . .
O1 O 0.63496(14) 0.56067(12) 1.04540(11) 0.0144(3) Uani 1 1 d . . . . .
N1 N 0.49799(16) 0.72737(14) 0.89394(13) 0.0110(3) Uani 1 1 d . . . . .
H1 H 0.5121 0.6964 0.9662 0.013 Uiso 1 1 calc R . . . .
N2 N 0.67263(16) 0.57304(14) 0.85008(13) 0.0109(3) Uani 1 1 d . . . . .
H2 H 0.7209 0.5368 0.7963 0.013 Uiso 1 1 calc R . . . .
C3 C 0.44530(19) 0.96000(17) 0.85930(15) 0.0110(3) Uani 1 1 d . . . . .
C9 C 0.70069(19) 0.52277(16) 0.96183(15) 0.0101(3) Uani 1 1 d . . . . .
C1 C 0.57666(18) 0.67417(16) 0.81430(15) 0.0099(3) Uani 1 1 d . . . . .
C2 C 0.38987(19) 0.83325(16) 0.87090(16) 0.0121(3) Uani 1 1 d . . . . .
H2A H 0.3079 0.8216 0.9342 0.015 Uiso 1 1 calc R . . . .
H2B H 0.3519 0.8331 0.7987 0.015 Uiso 1 1 calc R . . . .
C14 C 0.8108(2) 0.83187(17) 0.40851(15) 0.0113(3) Uani 1 1 d . . . . .
C19 C 0.66223(19) 0.81709(17) 0.41207(15) 0.0124(3) Uani 1 1 d . . . . .
H19 H 0.5923 0.8839 0.4240 0.015 Uiso 1 1 calc R . . . .
C11 C 0.8908(2) 0.35398(18) 0.89819(16) 0.0148(4) Uani 1 1 d . . . . .
H11 H 0.8699 0.3641 0.8217 0.018 Uiso 1 1 calc R . . . .
C15 C 0.91257(19) 0.72839(17) 0.39094(15) 0.0116(3) Uani 1 1 d . . . . .
H15 H 1.0130 0.7352 0.3895 0.014 Uiso 1 1 calc R . . . .
C4 C 0.3501(2) 1.05301(17) 0.89697(16) 0.0137(4) Uani 1 1 d . . . . .
H4 H 0.2547 1.0344 0.9320 0.016 Uiso 1 1 calc R . . . .
C17 C 0.7166(2) 0.60365(18) 0.37901(15) 0.0132(4) Uani 1 1 d . . . . .
C6 C 0.5321(2) 1.20050(18) 0.83417(16) 0.0161(4) Uani 1 1 d . . . . .
H6 H 0.5616 1.2820 0.8255 0.019 Uiso 1 1 calc R . . . .
C16 C 0.86738(19) 0.61675(17) 0.37569(15) 0.0119(3) Uani 1 1 d . . . . .
H16 H 0.9372 0.5501 0.3632 0.014 Uiso 1 1 calc R . . . .
C5 C 0.3925(2) 1.17279(18) 0.88411(16) 0.0158(4) Uani 1 1 d . . . . .
H5 H 0.3259 1.2355 0.9095 0.019 Uiso 1 1 calc R . . . .
C18 C 0.61486(19) 0.70405(18) 0.39819(15) 0.0125(3) Uani 1 1 d . . . . .
H18 H 0.5143 0.6962 0.4019 0.015 Uiso 1 1 calc R . . . .
C8 C 0.5857(2) 0.98843(18) 0.80909(16) 0.0152(4) Uani 1 1 d . . . . .
H8 H 0.6522 0.9260 0.7832 0.018 Uiso 1 1 calc R . . . .
C20 C 0.8672(2) 0.94875(17) 0.42439(16) 0.0146(4) Uani 1 1 d . . . . .
H20 H 0.9428 0.9216 0.4774 0.018 Uiso 1 1 calc R . . . .
C7 C 0.6285(2) 1.10807(19) 0.79693(16) 0.0176(4) Uani 1 1 d . . . . .
H7 H 0.7242 1.1267 0.7629 0.021 Uiso 1 1 calc R . . . .
C10 C 0.81799(19) 0.42182(16) 0.97532(15) 0.0110(3) Uani 1 1 d . . . . .
C22 C 0.9417(2) 1.01898(19) 0.30739(18) 0.0203(4) Uani 1 1 d . . . . .
H22A H 1.0197 0.9635 0.2772 0.031 Uiso 1 1 calc GR . . . .
H22B H 0.9823 1.0928 0.3176 0.031 Uiso 1 1 calc GR . . . .
H22C H 0.8705 1.0453 0.2529 0.031 Uiso 1 1 calc GR . . . .
C13 C 1.0095(2) 0.27277(19) 1.05812(17) 0.0180(4) Uani 1 1 d . . . . .
H13 H 1.0778 0.2219 1.1036 0.022 Uiso 1 1 calc R . . . .
C21 C 0.7518(2) 1.03550(19) 0.47780(19) 0.0226(4) Uani 1 1 d . . . . .
H21A H 0.6792 1.0679 0.4253 0.034 Uiso 1 1 calc GR . . . .
H21B H 0.7975 1.1054 0.4907 0.034 Uiso 1 1 calc GR . . . .
H21C H 0.7047 0.9888 0.5516 0.034 Uiso 1 1 calc GR . . . .
C12 C 1.0004(2) 0.26746(19) 0.94730(18) 0.0189(4) Uani 1 1 d . . . . .
H12 H 1.0609 0.2119 0.9076 0.023 Uiso 1 1 calc R . . . .
C23 C 0.6681(2) 0.48442(19) 0.36481(16) 0.0170(4) Uani 1 1 d . . . . .
H23A H 0.7369 0.4143 0.3936 0.025 Uiso 1 1 calc GR . . . .
H23B H 0.6639 0.4900 0.2829 0.025 Uiso 1 1 calc GR . . . .
H23C H 0.5717 0.4710 0.4086 0.025 Uiso 1 1 calc GR . . . .


_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 Cl2 2.4382(5) . ?
Ru1 Cl1 2.4342(5) . ?
Ru1 S1 2.4073(5) . ?
Ru1 C14 2.1901(18) . ?
Ru1 C19 2.1684(18) . ?
Ru1 C15 2.1677(17) . ?
Ru1 C17 2.2209(17) . ?
Ru1 C16 2.2009(17) . ?
Ru1 C18 2.1852(17) . ?
S1 C1 1.7021(18) . ?
S2 C10 1.7231(18) . ?
S2 C13 1.706(2) . ?
O1 C9 1.231(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.325(2) . ?
N1 C2 1.458(2) . ?
N2 H2 0.8800 . ?
N2 C9 1.381(2) . ?
N2 C1 1.377(2) . ?
C3 C2 1.518(2) . ?
C3 C4 1.393(2) . ?
C3 C8 1.397(3) . ?
C9 C10 1.470(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C14 C19 1.414(3) . ?
C14 C15 1.434(2) . ?
C14 C20 1.514(2) . ?
C19 H19 0.9500 . ?
C19 C18 1.427(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.380(3) . ?
C11 C12 1.417(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.410(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.392(3) . ?
C17 C16 1.431(3) . ?
C17 C18 1.413(3) . ?
C17 C23 1.498(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.388(3) . ?
C6 C7 1.392(3) . ?
C16 H16 0.9500 . ?
C5 H5 0.9500 . ?
C18 H18 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.393(3) . ?
C20 H20 1.0000 . ?
C20 C22 1.539(3) . ?
C20 C21 1.529(3) . ?
C7 H7 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C12 1.366(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C12 H12 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
Cl1 Ru1 Cl2 88.875(16) . . ?
S1 Ru1 Cl2 92.309(16) . . ?
S1 Ru1 Cl1 89.225(19) . . ?
C14 Ru1 Cl2 162.18(5) . . ?
C14 Ru1 Cl1 92.93(5) . . ?
C14 Ru1 S1 105.44(5) . . ?
C14 Ru1 C17 81.63(7) . . ?
C14 Ru1 C16 68.92(7) . . ?
C19 Ru1 Cl2 146.54(5) . . ?
C19 Ru1 Cl1 124.24(5) . . ?
C19 Ru1 S1 84.29(5) . . ?
C19 Ru1 C14 37.86(7) . . ?
C19 Ru1 C17 68.35(7) . . ?
C19 Ru1 C16 80.60(7) . . ?
C19 Ru1 C18 38.28(7) . . ?
C15 Ru1 Cl2 124.17(5) . . ?
C15 Ru1 Cl1 86.69(5) . . ?
C15 Ru1 S1 143.15(5) . . ?
C15 Ru1 C14 38.43(6) . . ?
C15 Ru1 C19 68.28(7) . . ?
C15 Ru1 C17 68.25(7) . . ?
C15 Ru1 C16 37.66(7) . . ?
C15 Ru1 C18 80.76(7) . . ?
C17 Ru1 Cl2 86.98(5) . . ?
C17 Ru1 Cl1 146.03(5) . . ?
C17 Ru1 S1 124.61(5) . . ?
C16 Ru1 Cl2 93.74(5) . . ?
C16 Ru1 Cl1 109.13(5) . . ?
C16 Ru1 S1 160.75(5) . . ?
C16 Ru1 C17 37.75(7) . . ?
C18 Ru1 Cl2 109.12(5) . . ?
C18 Ru1 Cl1 161.76(5) . . ?
C18 Ru1 S1 92.91(5) . . ?
C18 Ru1 C14 69.03(7) . . ?
C18 Ru1 C17 37.41(7) . . ?
C18 Ru1 C16 67.85(7) . . ?
C1 S1 Ru1 116.61(6) . . ?
C13 S2 C10 91.21(9) . . ?
C1 N1 H1 117.5 . . ?
C1 N1 C2 124.96(15) . . ?
C2 N1 H1 117.5 . . ?
C9 N2 H2 116.7 . . ?
C1 N2 H2 116.7 . . ?
C1 N2 C9 126.55(15) . . ?
C4 C3 C2 118.30(16) . . ?
C4 C3 C8 118.79(17) . . ?
C8 C3 C2 122.87(16) . . ?
O1 C9 N2 123.01(16) . . ?
O1 C9 C10 121.35(16) . . ?
N2 C9 C10 115.61(15) . . ?
N1 C1 S1 120.93(13) . . ?
N1 C1 N2 118.06(16) . . ?
N2 C1 S1 121.01(13) . . ?
N1 C2 C3 114.61(15) . . ?
N1 C2 H2A 108.6 . . ?
N1 C2 H2B 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C19 C14 Ru1 70.24(10) . . ?
C19 C14 C15 117.37(16) . . ?
C19 C14 C20 123.83(16) . . ?
C15 C14 Ru1 69.94(10) . . ?
C15 C14 C20 118.80(16) . . ?
C20 C14 Ru1 129.86(12) . . ?
Ru1 C19 H19 130.0 . . ?
C14 C19 Ru1 71.90(10) . . ?
C14 C19 H19 119.2 . . ?
C14 C19 C18 121.51(16) . . ?
C18 C19 Ru1 71.50(10) . . ?
C18 C19 H19 119.2 . . ?
C10 C11 H11 124.2 . . ?
C10 C11 C12 111.63(17) . . ?
C12 C11 H11 124.2 . . ?
Ru1 C15 H15 129.3 . . ?
C14 C15 Ru1 71.63(10) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 Ru1 72.45(10) . . ?
C16 C15 C14 121.71(16) . . ?
C16 C15 H15 119.1 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.05(17) . . ?
C5 C4 H4 119.5 . . ?
C16 C17 Ru1 70.37(10) . . ?
C16 C17 C23 120.28(17) . . ?
C18 C17 Ru1 69.92(10) . . ?
C18 C17 C16 118.78(17) . . ?
C18 C17 C23 120.93(17) . . ?
C23 C17 Ru1 130.75(13) . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.56(18) . . ?
C7 C6 H6 120.2 . . ?
Ru1 C16 H16 131.0 . . ?
C15 C16 Ru1 69.89(10) . . ?
C15 C16 C17 120.16(16) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 Ru1 71.88(10) . . ?
C17 C16 H16 119.9 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.90(17) . . ?
C6 C5 H5 120.0 . . ?
Ru1 C18 H18 129.8 . . ?
C19 C18 Ru1 70.23(10) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 Ru1 72.67(10) . . ?
C17 C18 C19 120.47(16) . . ?
C17 C18 H18 119.8 . . ?
C3 C8 H8 119.9 . . ?
C7 C8 C3 120.17(17) . . ?
C7 C8 H8 119.9 . . ?
C14 C20 H20 107.6 . . ?
C14 C20 C22 108.95(15) . . ?
C14 C20 C21 114.20(16) . . ?
C22 C20 H20 107.6 . . ?
C21 C20 H20 107.6 . . ?
C21 C20 C22 110.74(16) . . ?
C6 C7 C8 120.52(18) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C10 S2 117.18(13) . . ?
C11 C10 S2 111.99(14) . . ?
C11 C10 C9 130.80(16) . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S2 C13 H13 123.7 . . ?
C12 C13 S2 112.58(15) . . ?
C12 C13 H13 123.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C12 H12 123.7 . . ?
C13 C12 C11 112.59(17) . . ?
C13 C12 H12 123.7 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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 O1 0.88 1.93 2.633(2) 135.4 .
N2 H2 Cl2 0.88 2.37 3.1813(15) 153.4 .
N2 H2 Cl1 0.88 2.73 3.1656(16) 112.2 .
C11 H11 Cl2 0.95 2.63 3.5361(19) 160.1 .

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 S1 C1 N1 164.03(12) . . . . ?
Ru1 S1 C1 N2 -15.42(17) . . . . ?
Ru1 C14 C19 C18 -53.70(15) . . . . ?
Ru1 C14 C15 C16 54.64(15) . . . . ?
Ru1 C14 C20 C22 160.27(14) . . . . ?
Ru1 C14 C20 C21 -75.3(2) . . . . ?
Ru1 C19 C18 C17 -54.63(15) . . . . ?
Ru1 C15 C16 C17 53.43(15) . . . . ?
Ru1 C17 C16 C15 -52.52(15) . . . . ?
Ru1 C17 C18 C19 53.50(15) . . . . ?
S2 C13 C12 C11 0.8(2) . . . . ?
O1 C9 C10 S2 -12.9(2) . . . . ?
O1 C9 C10 C11 169.68(19) . . . . ?
N2 C9 C10 S2 165.63(13) . . . . ?
N2 C9 C10 C11 -11.8(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C8 C7 C6 -0.2(3) . . . . ?
C9 N2 C1 S1 176.71(14) . . . . ?
C9 N2 C1 N1 -2.8(3) . . . . ?
C1 N1 C2 C3 -95.3(2) . . . . ?
C1 N2 C9 O1 3.9(3) . . . . ?
C1 N2 C9 C10 -174.59(16) . . . . ?
C2 N1 C1 S1 1.8(2) . . . . ?
C2 N1 C1 N2 -178.76(16) . . . . ?
C2 C3 C4 C5 -177.19(17) . . . . ?
C2 C3 C8 C7 177.53(17) . . . . ?
C14 C19 C18 Ru1 53.89(15) . . . . ?
C14 C19 C18 C17 -0.7(3) . . . . ?
C14 C15 C16 Ru1 -54.27(15) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C19 C14 C15 Ru1 -53.54(14) . . . . ?
C19 C14 C15 C16 1.1(3) . . . . ?
C19 C14 C20 C22 -108.05(19) . . . . ?
C19 C14 C20 C21 16.3(2) . . . . ?
C15 C14 C19 Ru1 53.40(14) . . . . ?
C15 C14 C19 C18 -0.3(3) . . . . ?
C15 C14 C20 C22 73.2(2) . . . . ?
C15 C14 C20 C21 -162.42(17) . . . . ?
C4 C3 C2 N1 -146.80(16) . . . . ?
C4 C3 C8 C7 -0.2(3) . . . . ?
C16 C17 C18 Ru1 -52.49(15) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C18 C17 C16 Ru1 52.28(14) . . . . ?
C18 C17 C16 C15 -0.2(3) . . . . ?
C8 C3 C2 N1 35.4(2) . . . . ?
C8 C3 C4 C5 0.7(3) . . . . ?
C20 C14 C19 Ru1 -125.38(17) . . . . ?
C20 C14 C19 C18 -179.08(16) . . . . ?
C20 C14 C15 Ru1 125.30(15) . . . . ?
C20 C14 C15 C16 179.94(16) . . . . ?
C7 C6 C5 C4 0.2(3) . . . . ?
C10 S2 C13 C12 -0.36(17) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C13 S2 C10 C9 -178.03(15) . . . . ?
C13 S2 C10 C11 -0.13(15) . . . . ?
C12 C11 C10 S2 0.6(2) . . . . ?
C12 C11 C10 C9 178.11(18) . . . . ?
C23 C17 C16 Ru1 -126.46(16) . . . . ?
C23 C17 C16 C15 -178.98(16) . . . . ?
C23 C17 C18 Ru1 126.24(16) . . . . ?
C23 C17 C18 C19 179.75(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_kjrutunap
_database_code_depnum_ccdc_archive 'CCDC 1443344'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_audit_creation_date             2015-04-29
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H26 Cl2 N2 O Ru S2'
_chemical_formula_sum            'C26 H26 Cl2 N2 O Ru S2'
_chemical_formula_weight         618.58
_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'
S S 0.1246 0.1234 '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                   10.628(2)
_cell_length_b                   20.991(4)
_cell_length_c                   12.334(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.720(2)
_cell_angle_gamma                90
_cell_volume                     2621.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.449
_cell_measurement_theta_min      2.220
_shelx_estimated_absorpt_T_max   0.791
_shelx_estimated_absorpt_T_min   0.604
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1161 before and 0.0480 after correction.
The Ratio of minimum to maximum transmission is 0.8155.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.57
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29930
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.516
_diffrn_reflns_theta_min         1.986
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5476
_reflns_number_total             5933
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_refine_diff_density_max         2.382
_refine_diff_density_min         -0.955
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.106
_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)+(0.0201P)²+5.3965P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0765
_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
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C8(H8), C21(H21), C18(H18), C22(H22), C19(H19), C5(H5),
 C16(H16), C7(H7), C15(H15), C14(H14), C6(H6), C9(H9), C10(H10), C11(H11)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.46288(2) 0.46860(2) 0.26421(2) 0.01586(6) Uani 1 1 d . . . . .
Cl2 Cl 0.37322(6) 0.38715(3) 0.35961(5) 0.02302(13) Uani 1 1 d . . . . .
Cl1 Cl 0.33339(6) 0.42334(4) 0.08296(5) 0.02679(15) Uani 1 1 d . . . . .
S1 S 0.28528(6) 0.53967(3) 0.26713(6) 0.02169(14) Uani 1 1 d . . . . .
S2 S -0.14270(7) 0.30285(3) 0.09480(7) 0.03269(17) Uani 1 1 d . . . . .
O1 O -0.1132(2) 0.43897(10) 0.1580(2) 0.0361(5) Uani 1 1 d . . . . .
N2 N 0.1097(2) 0.44668(11) 0.1898(2) 0.0227(5) Uani 1 1 d . . . . .
H2 H 0.1797 0.4252 0.1870 0.027 Uiso 1 1 calc R . . . .
N1 N 0.0247(2) 0.54411(10) 0.2196(2) 0.0223(5) Uani 1 1 d . . . . .
H1 H -0.0536 0.5260 0.1948 0.027 Uiso 1 1 calc R . . . .
C2 C 0.0300(3) 0.60951(12) 0.2541(2) 0.0208(5) Uani 1 1 d . . . . .
C3 C -0.0090(2) 0.62487(12) 0.3514(2) 0.0193(5) Uani 1 1 d . . . . .
C8 C -0.0521(3) 0.57905(14) 0.4166(2) 0.0254(6) Uani 1 1 d . . . . .
H8 H -0.0536 0.5353 0.3967 0.030 Uiso 1 1 calc R . . . .
C13 C 0.0009(3) 0.34656(12) 0.1335(2) 0.0202(5) Uani 1 1 d . . . . .
C21 C 0.6459(2) 0.44236(13) 0.2289(2) 0.0234(5) Uani 1 1 d . . . . .
H21 H 0.6625 0.4100 0.1812 0.028 Uiso 1 1 calc R . . . .
C18 C 0.5958(3) 0.53910(14) 0.3672(2) 0.0240(6) Uani 1 1 d . . . . .
H18 H 0.5801 0.5716 0.4152 0.029 Uiso 1 1 calc R . . . .
C12 C -0.0083(3) 0.41383(13) 0.1609(2) 0.0213(5) Uani 1 1 d . . . . .
C22 C 0.6032(2) 0.50341(13) 0.1820(2) 0.0197(5) Uani 1 1 d . . . . .
H22 H 0.5914 0.5109 0.1035 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6357(3) 0.47855(15) 0.4126(2) 0.0283(6) Uani 1 1 d . . . . .
H19 H 0.6442 0.4703 0.4903 0.034 Uiso 1 1 calc R . . . .
C4 C -0.0052(3) 0.69031(13) 0.3836(2) 0.0255(6) Uani 1 1 d . . . . .
C20 C 0.6639(3) 0.42896(14) 0.3439(3) 0.0281(6) Uani 1 1 d . . . . .
C1 C 0.1296(3) 0.50894(12) 0.2224(2) 0.0189(5) Uani 1 1 d . . . . .
C23 C 0.5307(3) 0.61791(13) 0.2013(2) 0.0228(5) Uani 1 1 d . . . . .
H23 H 0.4827 0.6377 0.2511 0.027 Uiso 1 1 calc R . . . .
C5 C 0.0379(3) 0.73678(13) 0.3190(3) 0.0333(7) Uani 1 1 d . . . . .
H5 H 0.0424 0.7803 0.3412 0.040 Uiso 1 1 calc R . . . .
C16 C -0.0610(3) 0.23663(14) 0.0743(3) 0.0327(7) Uani 1 1 d . . . . .
H16 H -0.1031 0.1971 0.0488 0.039 Uiso 1 1 calc R . . . .
C24 C 0.4359(3) 0.61539(15) 0.0804(3) 0.0310(6) Uani 1 1 d . . . . .
H24A H 0.4849 0.6045 0.0274 0.047 Uiso 1 1 calc GR . . . .
H24B H 0.3937 0.6571 0.0602 0.047 Uiso 1 1 calc GR . . . .
H24C H 0.3681 0.5830 0.0761 0.047 Uiso 1 1 calc GR . . . .
C7 C 0.0680(3) 0.65561(14) 0.1917(3) 0.0297(6) Uani 1 1 d . . . . .
H7 H 0.0910 0.6443 0.1256 0.036 Uiso 1 1 calc R . . . .
C15 C 0.0702(3) 0.24625(14) 0.0981(3) 0.0337(7) Uani 1 1 d . . . . .
H15 H 0.1309 0.2141 0.0924 0.040 Uiso 1 1 calc R . . . .
C14 C 0.1070(3) 0.30982(14) 0.1325(3) 0.0294(6) Uani 1 1 d . . . . .
H14 H 0.1952 0.3252 0.1526 0.035 Uiso 1 1 calc R . . . .
C25 C 0.6506(3) 0.65975(14) 0.2073(3) 0.0315(7) Uani 1 1 d . . . . .
H25A H 0.7095 0.6609 0.2857 0.047 Uiso 1 1 calc GR . . . .
H25B H 0.6210 0.7031 0.1825 0.047 Uiso 1 1 calc GR . . . .
H25C H 0.6981 0.6421 0.1573 0.047 Uiso 1 1 calc GR . . . .
C6 C 0.0728(3) 0.71971(15) 0.2258(3) 0.0380(8) Uani 1 1 d . . . . .
H6 H 0.1008 0.7514 0.1832 0.046 Uiso 1 1 calc R . . . .
C9 C -0.0915(3) 0.59706(17) 0.5080(3) 0.0336(7) Uani 1 1 d . . . . .
H9 H -0.1213 0.5658 0.5503 0.040 Uiso 1 1 calc R . . . .
C10 C -0.0881(3) 0.66159(18) 0.5393(3) 0.0396(8) Uani 1 1 d . . . . .
H10 H -0.1158 0.6738 0.6026 0.048 Uiso 1 1 calc R . . . .
C11 C -0.0456(3) 0.70651(16) 0.4797(3) 0.0360(8) Uani 1 1 d . . . . .
H11 H -0.0428 0.7498 0.5027 0.043 Uiso 1 1 calc R . . . .
C26 C 0.7030(3) 0.36352(17) 0.3921(3) 0.0437(9) Uani 1 1 d . . . . .
H26A H 0.6544 0.3530 0.4456 0.066 Uiso 1 1 calc GR . . . .
H26B H 0.7981 0.3627 0.4319 0.066 Uiso 1 1 calc GR . . . .
H26C H 0.6821 0.3323 0.3301 0.066 Uiso 1 1 calc GR . . . .
C17 C 0.5781(2) 0.55300(12) 0.2494(2) 0.0184(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
Ru1 Cl2 2.4286(7) . ?
Ru1 Cl1 2.4333(7) . ?
Ru1 S1 2.4147(7) . ?
Ru1 C21 2.189(3) . ?
Ru1 C18 2.169(3) . ?
Ru1 C22 2.170(2) . ?
Ru1 C19 2.173(3) . ?
Ru1 C20 2.224(3) . ?
Ru1 C17 2.193(3) . ?
S1 C1 1.704(3) . ?
S2 C13 1.719(3) . ?
S2 C16 1.698(3) . ?
O1 C12 1.224(3) . ?
N2 H2 0.8800 . ?
N2 C12 1.379(3) . ?
N2 C1 1.365(3) . ?
N1 H1 0.8800 . ?
N1 C2 1.433(3) . ?
N1 C1 1.329(3) . ?
C2 C3 1.421(4) . ?
C2 C7 1.372(4) . ?
C3 C8 1.416(4) . ?
C3 C4 1.427(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(4) . ?
C13 C12 1.462(4) . ?
C13 C14 1.370(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.422(4) . ?
C21 C20 1.400(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.402(4) . ?
C18 C17 1.437(4) . ?
C22 H22 0.9500 . ?
C22 C17 1.408(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.431(5) . ?
C4 C5 1.421(4) . ?
C4 C11 1.419(4) . ?
C20 C26 1.504(4) . ?
C23 H23 1.0000 . ?
C23 C24 1.526(4) . ?
C23 C25 1.531(4) . ?
C23 C17 1.510(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.359(5) . ?
C16 H16 0.9500 . ?
C16 C15 1.350(5) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C6 1.406(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.419(4) . ?
C14 H14 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C6 H6 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.406(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.355(5) . ?
C11 H11 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
Cl2 Ru1 Cl1 88.55(3) . . ?
S1 Ru1 Cl2 90.23(3) . . ?
S1 Ru1 Cl1 91.65(3) . . ?
C21 Ru1 Cl2 115.01(8) . . ?
C21 Ru1 Cl1 90.42(8) . . ?
C21 Ru1 S1 154.73(7) . . ?
C21 Ru1 C20 36.99(11) . . ?
C21 Ru1 C17 68.53(10) . . ?
C18 Ru1 Cl2 118.57(7) . . ?
C18 Ru1 Cl1 152.82(7) . . ?
C18 Ru1 S1 86.70(8) . . ?
C18 Ru1 C21 80.12(11) . . ?
C18 Ru1 C22 68.05(10) . . ?
C18 Ru1 C19 37.66(11) . . ?
C18 Ru1 C20 68.27(11) . . ?
C18 Ru1 C17 38.46(9) . . ?
C22 Ru1 Cl2 152.93(7) . . ?
C22 Ru1 Cl1 88.79(7) . . ?
C22 Ru1 S1 116.78(7) . . ?
C22 Ru1 C21 38.09(10) . . ?
C22 Ru1 C19 80.58(10) . . ?
C22 Ru1 C20 68.15(10) . . ?
C22 Ru1 C17 37.64(10) . . ?
C19 Ru1 Cl2 90.88(8) . . ?
C19 Ru1 Cl1 155.25(9) . . ?
C19 Ru1 S1 113.09(9) . . ?
C19 Ru1 C21 67.49(11) . . ?
C19 Ru1 C20 37.96(12) . . ?
C19 Ru1 C17 69.03(10) . . ?
C20 Ru1 Cl2 89.34(8) . . ?
C20 Ru1 Cl1 117.29(9) . . ?
C20 Ru1 S1 151.03(9) . . ?
C17 Ru1 Cl2 157.02(7) . . ?
C17 Ru1 Cl1 114.38(7) . . ?
C17 Ru1 S1 87.76(7) . . ?
C17 Ru1 C20 81.56(10) . . ?
C1 S1 Ru1 116.61(9) . . ?
C16 S2 C13 91.58(14) . . ?
C12 N2 H2 116.5 . . ?
C1 N2 H2 116.5 . . ?
C1 N2 C12 127.0(2) . . ?
C2 N1 H1 117.7 . . ?
C1 N1 H1 117.7 . . ?
C1 N1 C2 124.5(2) . . ?
C3 C2 N1 118.2(2) . . ?
C7 C2 N1 120.1(2) . . ?
C7 C2 C3 121.7(3) . . ?
C2 C3 C4 117.6(2) . . ?
C8 C3 C2 123.6(2) . . ?
C8 C3 C4 118.8(3) . . ?
C3 C8 H8 119.6 . . ?
C9 C8 C3 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C12 C13 S2 117.7(2) . . ?
C14 C13 S2 111.2(2) . . ?
C14 C13 C12 131.2(2) . . ?
Ru1 C21 H21 130.3 . . ?
C22 C21 Ru1 70.23(14) . . ?
C22 C21 H21 119.3 . . ?
C20 C21 Ru1 72.86(16) . . ?
C20 C21 H21 119.3 . . ?
C20 C21 C22 121.4(3) . . ?
Ru1 C18 H18 130.4 . . ?
C19 C18 Ru1 71.32(16) . . ?
C19 C18 H18 119.4 . . ?
C19 C18 C17 121.3(3) . . ?
C17 C18 Ru1 71.66(14) . . ?
C17 C18 H18 119.4 . . ?
O1 C12 N2 122.7(2) . . ?
O1 C12 C13 122.3(2) . . ?
N2 C12 C13 115.1(2) . . ?
Ru1 C22 H22 129.4 . . ?
C21 C22 Ru1 71.68(15) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 Ru1 72.06(14) . . ?
C17 C22 C21 121.3(2) . . ?
C17 C22 H22 119.3 . . ?
Ru1 C19 H19 128.9 . . ?
C18 C19 Ru1 71.02(15) . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 121.0(3) . . ?
C20 C19 Ru1 72.94(16) . . ?
C20 C19 H19 119.5 . . ?
C5 C4 C3 119.4(3) . . ?
C11 C4 C3 118.3(3) . . ?
C11 C4 C5 122.3(3) . . ?
C21 C20 Ru1 70.15(15) . . ?
C21 C20 C19 117.7(3) . . ?
C21 C20 C26 121.3(3) . . ?
C19 C20 Ru1 69.10(16) . . ?
C19 C20 C26 120.8(3) . . ?
C26 C20 Ru1 129.0(2) . . ?
N2 C1 S1 120.40(19) . . ?
N1 C1 S1 121.5(2) . . ?
N1 C1 N2 118.1(2) . . ?
C24 C23 H23 107.8 . . ?
C24 C23 C25 111.1(2) . . ?
C25 C23 H23 107.8 . . ?
C17 C23 H23 107.8 . . ?
C17 C23 C24 113.2(2) . . ?
C17 C23 C25 109.0(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
S2 C16 H16 123.6 . . ?
C15 C16 S2 112.7(2) . . ?
C15 C16 H16 123.6 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 C7 H7 120.1 . . ?
C2 C7 C6 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C16 C15 H15 123.9 . . ?
C16 C15 C14 112.2(3) . . ?
C14 C15 H15 123.9 . . ?
C13 C14 C15 112.3(3) . . ?
C13 C14 H14 123.9 . . ?
C15 C14 H14 123.9 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C4 C11 H11 119.3 . . ?
C10 C11 C4 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C20 C26 H26A 109.5 . . ?
C20 C26 H26B 109.5 . . ?
C20 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C18 C17 Ru1 69.88(14) . . ?
C18 C17 C23 120.4(2) . . ?
C22 C17 Ru1 70.29(14) . . ?
C22 C17 C18 117.2(2) . . ?
C22 C17 C23 122.4(2) . . ?
C23 C17 Ru1 129.33(17) . . ?

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
N2 H2 Cl2 0.88 2.60 3.197(2) 126.4 .
N2 H2 Cl1 0.88 2.36 3.088(2) 139.6 .
N1 H1 O1 0.88 1.94 2.630(3) 134.0 .

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 S1 C1 N2 1.6(2) . . . . ?
Ru1 S1 C1 N1 -179.34(18) . . . . ?
Ru1 C21 C22 C17 54.5(2) . . . . ?
Ru1 C21 C20 C19 -51.8(2) . . . . ?
Ru1 C21 C20 C26 124.3(3) . . . . ?
Ru1 C18 C19 C20 55.3(2) . . . . ?
Ru1 C18 C17 C22 -53.7(2) . . . . ?
Ru1 C18 C17 C23 124.6(2) . . . . ?
Ru1 C22 C17 C18 53.5(2) . . . . ?
Ru1 C22 C17 C23 -124.8(2) . . . . ?
Ru1 C19 C20 C21 52.3(2) . . . . ?
Ru1 C19 C20 C26 -123.8(3) . . . . ?
S2 C13 C12 O1 0.8(4) . . . . ?
S2 C13 C12 N2 -179.16(19) . . . . ?
S2 C13 C14 C15 1.1(3) . . . . ?
S2 C16 C15 C14 -1.0(4) . . . . ?
N1 C2 C3 C8 0.5(4) . . . . ?
N1 C2 C3 C4 -179.0(2) . . . . ?
N1 C2 C7 C6 179.9(3) . . . . ?
C2 N1 C1 S1 -0.9(4) . . . . ?
C2 N1 C1 N2 178.2(2) . . . . ?
C2 C3 C8 C9 -178.4(3) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C2 C3 C4 C11 179.2(2) . . . . ?
C2 C7 C6 C5 -1.2(5) . . . . ?
C3 C2 C7 C6 2.0(4) . . . . ?
C3 C8 C9 C10 -0.9(4) . . . . ?
C3 C4 C5 C6 1.4(4) . . . . ?
C3 C4 C11 C10 -0.6(4) . . . . ?
C8 C3 C4 C5 179.9(3) . . . . ?
C8 C3 C4 C11 -0.3(4) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C13 S2 C16 C15 1.4(3) . . . . ?
C21 C22 C17 Ru1 -54.3(2) . . . . ?
C21 C22 C17 C18 -0.8(4) . . . . ?
C21 C22 C17 C23 -179.0(2) . . . . ?
C18 C19 C20 Ru1 -54.5(2) . . . . ?
C18 C19 C20 C21 -2.1(4) . . . . ?
C18 C19 C20 C26 -178.2(3) . . . . ?
C12 N2 C1 S1 174.2(2) . . . . ?
C12 N2 C1 N1 -4.9(4) . . . . ?
C12 C13 C14 C15 -178.8(3) . . . . ?
C22 C21 C20 Ru1 52.9(2) . . . . ?
C22 C21 C20 C19 1.1(4) . . . . ?
C22 C21 C20 C26 177.1(3) . . . . ?
C19 C18 C17 Ru1 53.4(2) . . . . ?
C19 C18 C17 C22 -0.3(4) . . . . ?
C19 C18 C17 C23 178.0(2) . . . . ?
C4 C3 C8 C9 1.1(4) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C20 C21 C22 Ru1 -54.1(2) . . . . ?
C20 C21 C22 C17 0.4(4) . . . . ?
C1 N2 C12 O1 2.4(5) . . . . ?
C1 N2 C12 C13 -177.7(2) . . . . ?
C1 N1 C2 C3 -113.9(3) . . . . ?
C1 N1 C2 C7 68.1(4) . . . . ?
C5 C4 C11 C10 179.1(3) . . . . ?
C16 S2 C13 C12 178.5(2) . . . . ?
C16 S2 C13 C14 -1.4(2) . . . . ?
C16 C15 C14 C13 0.0(4) . . . . ?
C24 C23 C17 Ru1 -54.1(3) . . . . ?
C24 C23 C17 C18 -142.1(3) . . . . ?
C24 C23 C17 C22 36.1(3) . . . . ?
C7 C2 C3 C8 178.4(3) . . . . ?
C7 C2 C3 C4 -1.1(4) . . . . ?
C14 C13 C12 O1 -179.4(3) . . . . ?
C14 C13 C12 N2 0.7(4) . . . . ?
C25 C23 C17 Ru1 -178.3(2) . . . . ?
C25 C23 C17 C18 93.7(3) . . . . ?
C25 C23 C17 C22 -88.1(3) . . . . ?
C9 C10 C11 C4 0.9(5) . . . . ?
C11 C4 C5 C6 -178.4(3) . . . . ?
C17 C18 C19 Ru1 -53.6(2) . . . . ?
C17 C18 C19 C20 1.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_kjtunap
_database_code_depnum_ccdc_archive 'CCDC 1443346'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;



# start Validation Reply Form
_vrf_PLAT414_kjtunap             
;
PROBLEM: Short Intra D-H..H-X       H1     ..  H8      ..       1.88 Ang.  
RESPONSE: The flatness of the structure results in this short
distance.
;
# end Validation Reply Form



_audit_creation_date             2015-04-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H12 N2 O S2'
_chemical_formula_sum            'C16 H12 N2 O S2'
_chemical_formula_weight         312.40
_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'
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'
S S 0.1246 0.1234 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.808(3)
_cell_length_b                   5.9200(13)
_cell_length_c                   16.679(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.112(3)
_cell_angle_gamma                90
_cell_volume                     1424.0(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9986
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.421
_cell_measurement_theta_min      2.584
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.824
_exptl_absorpt_coefficient_mu    0.373
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1436 before and 0.0872 after correction.
The Ratio of minimum to maximum transmission is 0.4461.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0633
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.421
_diffrn_reflns_theta_min         1.412
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2861
_reflns_number_total             3221
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.499
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0713P)²+1.0477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1264
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Restrained distances
 C13A-C12 \\sim C13-C12
 with sigma of 0.005
3. Restrained planarity
 S2A, C13A, C14A, C15A, C16A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C13) = Uanis(C13A)
Uanis(S2) = Uanis(S2A)
Uanis(C14A) = Uanis(C14)
Uanis(C16A) = Uanis(C15) = Uanis(C15A) = Uanis(C16)
5. Same fragment restrains
{S2, C13, C14, C15, C16} sigma for 1-2: 0.005, 1-3: 0.04
as
{S2A, C13A, C14A, C15A, C16A}
6. Others
 Sof(S2A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=1-FVAR(1)
 Sof(S2)=Sof(C13)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C14A(H14A), C15A(H15A), C16A(H16A)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.48454(3) 0.63776(10) 0.38642(3) 0.03014(18) Uani 1 1 d . . . . .
O1 O 0.19664(9) 0.3593(2) 0.37791(7) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.29809(10) 0.6774(2) 0.33429(8) 0.0161(3) Uani 1 1 d . . . . .
H1 H 0.2454 0.6138 0.3377 0.019 Uiso 1 1 calc R . . . .
N2 N 0.35374(10) 0.3915(2) 0.42497(8) 0.0179(3) Uani 1 1 d . . . . .
H2 H 0.4014 0.3341 0.4605 0.021 Uiso 1 1 calc R . . . .
C1 C 0.37273(12) 0.5761(3) 0.37944(9) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.28744(12) 0.8683(3) 0.28178(9) 0.0161(3) Uani 1 1 d . . . . .
C3 C 0.19492(12) 0.9064(3) 0.23361(9) 0.0166(3) Uani 1 1 d . . . . .
C4 C 0.17848(13) 1.1053(3) 0.18461(10) 0.0185(4) Uani 1 1 d . . . . .
C5 C 0.25228(14) 1.2549(3) 0.18259(10) 0.0226(4) Uani 1 1 d . . . . .
H5 H 0.2409 1.3882 0.1501 0.027 Uiso 1 1 calc R . . . .
C6 C 0.33974(13) 1.2094(3) 0.22699(11) 0.0226(4) Uani 1 1 d . . . . .
H6 H 0.3890 1.3094 0.2240 0.027 Uiso 1 1 calc R . . . .
C7 C 0.35781(13) 1.0153(3) 0.27737(10) 0.0207(4) Uani 1 1 d . . . . .
H7 H 0.4189 0.9865 0.3083 0.025 Uiso 1 1 calc R . . . .
C8 C 0.11946(12) 0.7570(3) 0.23134(10) 0.0204(4) Uani 1 1 d . . . . .
H8 H 0.1290 0.6229 0.2634 0.025 Uiso 1 1 calc R . . . .
C9 C 0.03297(13) 0.8024(3) 0.18371(11) 0.0249(4) Uani 1 1 d . . . . .
H9 H -0.0165 0.6998 0.1832 0.030 Uiso 1 1 calc R . . . .
C10 C 0.01707(14) 1.0000(4) 0.13560(11) 0.0265(4) Uani 1 1 d . . . . .
H10 H -0.0429 1.0301 0.1025 0.032 Uiso 1 1 calc R . . . .
C11 C 0.08736(14) 1.1471(3) 0.13664(11) 0.0244(4) Uani 1 1 d . . . . .
H11 H 0.0757 1.2812 0.1047 0.029 Uiso 1 1 calc R . . . .
C12 C 0.26981(11) 0.2882(3) 0.42121(9) 0.0169(3) Uani 1 1 d D . . . .
S2 S 0.16329(4) -0.03722(11) 0.46609(4) 0.0219(2) Uani 0.865(2) 1 d D . P A 1
C13 C 0.2702(2) 0.0847(6) 0.4711(3) 0.0175(3) Uani 0.865(2) 1 d D . P A 1
C14 C 0.3385(3) -0.0371(6) 0.5200(2) 0.0257(8) Uani 0.865(2) 1 d D . P A 1
H14 H 0.4022 0.0021 0.5289 0.031 Uiso 0.865(2) 1 calc R . P A 1
C15 C 0.3071(2) -0.2256(5) 0.5562(2) 0.0246(4) Uani 0.865(2) 1 d D . P A 1
H15 H 0.3462 -0.3255 0.5932 0.030 Uiso 0.865(2) 1 calc R . P A 1
C16 C 0.2129(2) -0.2478(4) 0.53170(18) 0.0246(4) Uani 0.865(2) 1 d D . P A 1
H16 H 0.1789 -0.3669 0.5491 0.030 Uiso 0.865(2) 1 calc R . P A 1
S2A S 0.3614(4) -0.0482(11) 0.5314(4) 0.0219(2) Uani 0.135(2) 1 d D . P A 2
C13A C 0.2670(9) 0.084(3) 0.4699(16) 0.0175(3) Uani 0.135(2) 1 d D . P A 2
C14A C 0.1885(9) -0.026(3) 0.4749(12) 0.0257(8) Uani 0.135(2) 1 d D . P A 2
H14A H 0.1296 0.0214 0.4439 0.031 Uiso 0.135(2) 1 calc R . P A 2
C15A C 0.1975(14) -0.212(3) 0.5275(12) 0.0246(4) Uani 0.135(2) 1 d D . P A 2
H15A H 0.1480 -0.2991 0.5393 0.030 Uiso 0.135(2) 1 calc R . P A 2
C16A C 0.2901(12) -0.248(3) 0.5592(13) 0.0246(4) Uani 0.135(2) 1 d D . P A 2
H16A H 0.3130 -0.3729 0.5936 0.030 Uiso 0.135(2) 1 calc R . P A 2


_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
S1 C1 1.6734(18) . ?
O1 C12 1.232(2) . ?
N1 H1 0.8800 . ?
N1 C1 1.331(2) . ?
N1 C2 1.416(2) . ?
N2 H2 0.8800 . ?
N2 C1 1.396(2) . ?
N2 C12 1.373(2) . ?
C2 C3 1.440(2) . ?
C2 C7 1.373(2) . ?
C3 C4 1.422(2) . ?
C3 C8 1.419(2) . ?
C4 C5 1.413(3) . ?
C4 C11 1.426(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.365(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.413(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.372(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.408(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.354(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.464(2) . ?
C12 C13A 1.462(5) . ?
S2 C13 1.724(3) . ?
S2 C16 1.711(2) . ?
C13 C14 1.354(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.398(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.367(3) . ?
C16 H16 0.9500 . ?
S2A C13A 1.723(7) . ?
S2A C16A 1.717(6) . ?
C13A C14A 1.352(7) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.397(6) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.369(6) . ?
C16A H16A 0.9500 . ?

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
C1 N1 H1 113.9 . . ?
C1 N1 C2 132.15(15) . . ?
C2 N1 H1 113.9 . . ?
C1 N2 H2 116.0 . . ?
C12 N2 H2 116.0 . . ?
C12 N2 C1 127.99(14) . . ?
N1 C1 S1 128.52(14) . . ?
N1 C1 N2 114.64(15) . . ?
N2 C1 S1 116.82(12) . . ?
N1 C2 C3 115.38(14) . . ?
C7 C2 N1 124.05(15) . . ?
C7 C2 C3 120.54(15) . . ?
C4 C3 C2 117.88(15) . . ?
C8 C3 C2 124.10(15) . . ?
C8 C3 C4 118.01(15) . . ?
C3 C4 C11 118.89(16) . . ?
C5 C4 C3 120.01(16) . . ?
C5 C4 C11 121.09(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.46(16) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.77(17) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 C6 120.28(17) . . ?
C2 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C3 C8 H8 119.4 . . ?
C9 C8 C3 121.28(16) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 119.8 . . ?
C8 C9 C10 120.42(17) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.89(17) . . ?
C11 C10 H10 120.1 . . ?
C4 C11 H11 119.3 . . ?
C10 C11 C4 121.50(17) . . ?
C10 C11 H11 119.3 . . ?
O1 C12 N2 122.77(15) . . ?
O1 C12 C13 120.24(18) . . ?
O1 C12 C13A 118.4(5) . . ?
N2 C12 C13 116.98(17) . . ?
N2 C12 C13A 118.8(5) . . ?
C16 S2 C13 91.00(13) . . ?
C12 C13 S2 115.60(19) . . ?
C14 C13 C12 133.4(3) . . ?
C14 C13 S2 110.99(19) . . ?
C13 C14 H14 122.9 . . ?
C13 C14 C15 114.2(3) . . ?
C15 C14 H14 122.9 . . ?
C14 C15 H15 124.3 . . ?
C16 C15 C14 111.3(3) . . ?
C16 C15 H15 124.3 . . ?
S2 C16 H16 123.8 . . ?
C15 C16 S2 112.5(3) . . ?
C15 C16 H16 123.8 . . ?
C16A S2A C13A 90.5(8) . . ?
C12 C13A S2A 125.8(8) . . ?
C14A C13A C12 124.5(9) . . ?
C14A C13A S2A 109.7(7) . . ?
C13A C14A H14A 121.3 . . ?
C13A C14A C15A 117.3(14) . . ?
C15A C14A H14A 121.3 . . ?
C14A C15A H15A 126.0 . . ?
C16A C15A C14A 107.9(17) . . ?
C16A C15A H15A 126.0 . . ?
S2A C16A H16A 122.8 . . ?
C15A C16A S2A 114.4(15) . . ?
C15A C16A H16A 122.8 . . ?

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 O1 0.88 1.86 2.6132(19) 142.4 .
N2 H2 S1 0.88 2.73 3.4991(15) 146.9 3_666
N2 H2 S2A 0.88 2.68 3.139(6) 113.5 .

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
O1 C12 C13 S2 -1.6(4) . . . . ?
O1 C12 C13 C14 176.0(4) . . . . ?
O1 C12 C13A S2A 177.7(15) . . . . ?
O1 C12 C13A C14A -4(3) . . . . ?
N1 C2 C3 C4 175.16(14) . . . . ?
N1 C2 C3 C8 -5.5(2) . . . . ?
N1 C2 C7 C6 -176.04(15) . . . . ?
N2 C12 C13 S2 178.9(2) . . . . ?
N2 C12 C13 C14 -3.5(6) . . . . ?
N2 C12 C13A S2A -2(3) . . . . ?
N2 C12 C13A C14A 176.3(13) . . . . ?
C1 N1 C2 C3 171.08(16) . . . . ?
C1 N1 C2 C7 -11.1(3) . . . . ?
C1 N2 C12 O1 -4.4(3) . . . . ?
C1 N2 C12 C13 175.1(3) . . . . ?
C1 N2 C12 C13A 174.9(15) . . . . ?
C2 N1 C1 S1 -2.9(3) . . . . ?
C2 N1 C1 N2 178.76(15) . . . . ?
C2 C3 C4 C5 1.7(2) . . . . ?
C2 C3 C4 C11 -179.77(15) . . . . ?
C2 C3 C8 C9 -179.58(16) . . . . ?
C3 C2 C7 C6 1.6(2) . . . . ?
C3 C4 C5 C6 0.5(2) . . . . ?
C3 C4 C11 C10 -1.3(3) . . . . ?
C3 C8 C9 C10 0.0(3) . . . . ?
C4 C3 C8 C9 -0.3(2) . . . . ?
C4 C5 C6 C7 -1.6(3) . . . . ?
C5 C4 C11 C10 177.28(17) . . . . ?
C5 C6 C7 C2 0.6(3) . . . . ?
C7 C2 C3 C4 -2.7(2) . . . . ?
C7 C2 C3 C8 176.63(16) . . . . ?
C8 C3 C4 C5 -177.71(15) . . . . ?
C8 C3 C4 C11 0.9(2) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C4 1.0(3) . . . . ?
C11 C4 C5 C6 -178.09(16) . . . . ?
C12 N2 C1 S1 -170.24(13) . . . . ?
C12 N2 C1 N1 8.3(2) . . . . ?
C12 C13 C14 C15 -179.4(5) . . . . ?
C12 C13A C14A C15A -177(3) . . . . ?
S2 C13 C14 C15 -1.7(4) . . . . ?
C13 C12 C13A S2A -6(46) . . . . ?
C13 C12 C13A C14A 172(50) . . . . ?
C13 S2 C16 C15 0.0(3) . . . . ?
C13 C14 C15 C16 1.7(4) . . . . ?
C14 C15 C16 S2 -0.9(4) . . . . ?
C16 S2 C13 C12 179.1(4) . . . . ?
C16 S2 C13 C14 1.0(3) . . . . ?
S2A C13A C14A C15A 1.5(16) . . . . ?
C13A C12 C13 S2 -5(48) . . . . ?
C13A C12 C13 C14 173(48) . . . . ?
C13A S2A C16A C15A -3.4(18) . . . . ?
C13A C14A C15A C16A -4(2) . . . . ?
C14A C15A C16A S2A 5(2) . . . . ?
C16A S2A C13A C12 179(3) . . . . ?
C16A S2A C13A C14A 1.0(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jhtl1
_database_code_depnum_ccdc_archive 'CCDC 1443347'
_audit_update_record             
;
2015-12-18 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_audit_creation_date             2015-03-30
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2014.10.22 svn.r3046 for OlexSys, GUI svn.r4928)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H10 N2 O S2'
_chemical_formula_sum            'C12 H10 N2 O S2'
_chemical_formula_weight         262.34
_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'
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'
S S 0.1246 0.1234 '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                   9.669(2)
_cell_length_b                   4.7975(12)
_cell_length_c                   25.794(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.061(2)
_cell_angle_gamma                90
_cell_volume                     1184.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5906
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.430
_cell_measurement_theta_min      2.164
_shelx_estimated_absorpt_T_max   0.863
_shelx_estimated_absorpt_T_min   0.788
_exptl_absorpt_coefficient_mu    0.432
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1529 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.7888.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.471
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            12786
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         2.165
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2388
_reflns_number_total             2679
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2679
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.130
_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)+(0.0257P)²+1.0070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), C3(H3), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.98294(4) 0.96574(10) 0.61666(2) 0.02079(13) Uani 1 1 d . . . . .
S2 S 0.38263(5) 0.33097(11) 0.55142(2) 0.02176(13) Uani 1 1 d . . . . .
O1 O 0.77270(13) 0.6199(3) 0.65698(5) 0.0240(3) Uani 1 1 d . . . . .
N1 N 0.61062(14) 0.6139(3) 0.58332(5) 0.0147(3) Uani 1 1 d . . . . .
H1 H 0.5882 0.6935 0.5526 0.018 Uiso 1 1 calc R . . . .
N2 N 0.55186(15) 0.3003(3) 0.64401(5) 0.0154(3) Uani 1 1 d . . . . .
H2 H 0.6288 0.3694 0.6616 0.018 Uiso 1 1 calc R . . . .
C1 C 1.00834(19) 1.2104(4) 0.57105(8) 0.0229(4) Uani 1 1 d . . . . .
H1A H 1.0938 1.3073 0.5705 0.027 Uiso 1 1 calc R . . . .
C2 C 0.89223(19) 1.2514(4) 0.53541(7) 0.0218(4) Uani 1 1 d . . . . .
H2A H 0.8875 1.3804 0.5073 0.026 Uiso 1 1 calc R . . . .
C3 C 0.77932(18) 1.0801(4) 0.54504(7) 0.0168(4) Uani 1 1 d . . . . .
H3 H 0.6902 1.0812 0.5241 0.020 Uiso 1 1 calc R . . . .
C4 C 0.81323(17) 0.9126(4) 0.58795(7) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.73242(17) 0.7060(4) 0.61266(7) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.51864(17) 0.4098(4) 0.59656(6) 0.0148(3) Uani 1 1 d . . . . .
C7 C 0.48745(18) 0.0939(4) 0.67181(7) 0.0150(3) Uani 1 1 d . . . . .
C8 C 0.37316(18) -0.0676(4) 0.65212(7) 0.0172(4) Uani 1 1 d . . . . .
H8 H 0.3292 -0.0424 0.6171 0.021 Uiso 1 1 calc R . . . .
C9 C 0.32338(19) -0.2665(4) 0.68397(7) 0.0201(4) Uani 1 1 d . . . . .
H9 H 0.2456 -0.3784 0.6704 0.024 Uiso 1 1 calc R . . . .
C10 C 0.3853(2) -0.3044(4) 0.73519(7) 0.0224(4) Uani 1 1 d . . . . .
H10 H 0.3500 -0.4401 0.7567 0.027 Uiso 1 1 calc R . . . .
C11 C 0.4992(2) -0.1422(4) 0.75465(7) 0.0259(4) Uani 1 1 d . . . . .
H11 H 0.5424 -0.1671 0.7898 0.031 Uiso 1 1 calc R . . . .
C12 C 0.5506(2) 0.0556(4) 0.72344(7) 0.0223(4) Uani 1 1 d . . . . .
H12 H 0.6290 0.1657 0.7371 0.027 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
S1 C1 1.704(2) . ?
S1 C4 1.7220(17) . ?
S2 C6 1.6730(17) . ?
O1 C5 1.226(2) . ?
N1 H1 0.8800 . ?
N1 C5 1.380(2) . ?
N1 C6 1.397(2) . ?
N2 H2 0.8800 . ?
N2 C6 1.329(2) . ?
N2 C7 1.417(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.362(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.416(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.370(2) . ?
C4 C5 1.462(2) . ?
C7 C8 1.386(2) . ?
C7 C12 1.397(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?

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
C1 S1 C4 91.49(9) . . ?
C5 N1 H1 116.1 . . ?
C5 N1 C6 127.87(14) . . ?
C6 N1 H1 116.1 . . ?
C6 N2 H2 113.7 . . ?
C6 N2 C7 132.51(15) . . ?
C7 N2 H2 113.7 . . ?
S1 C1 H1A 123.8 . . ?
C2 C1 S1 112.38(14) . . ?
C2 C1 H1A 123.8 . . ?
C1 C2 H2A 123.8 . . ?
C1 C2 C3 112.36(17) . . ?
C3 C2 H2A 123.8 . . ?
C2 C3 H3 123.9 . . ?
C4 C3 C2 112.29(16) . . ?
C4 C3 H3 123.9 . . ?
C3 C4 S1 111.48(13) . . ?
C3 C4 C5 131.90(16) . . ?
C5 C4 S1 116.62(13) . . ?
O1 C5 N1 122.58(16) . . ?
O1 C5 C4 121.01(15) . . ?
N1 C5 C4 116.41(15) . . ?
N1 C6 S2 116.98(12) . . ?
N2 C6 S2 128.04(14) . . ?
N2 C6 N1 114.97(15) . . ?
C8 C7 N2 126.11(16) . . ?
C8 C7 C12 119.68(16) . . ?
C12 C7 N2 114.20(15) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.47(16) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.04(17) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.4 . . ?
C9 C10 C11 119.22(18) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.52(18) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 120.06(18) . . ?
C11 C12 H12 120.0 . . ?

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 S2 0.88 2.74 3.4953(17) 145.0 3_666
N2 H2 O1 0.88 1.85 2.612(2) 143.0 .

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
S1 C1 C2 C3 -0.1(2) . . . . ?
S1 C4 C5 O1 14.8(2) . . . . ?
S1 C4 C5 N1 -164.71(13) . . . . ?
N2 C7 C8 C9 178.64(16) . . . . ?
N2 C7 C12 C11 -179.12(17) . . . . ?
C1 S1 C4 C3 -0.28(14) . . . . ?
C1 S1 C4 C5 -179.88(14) . . . . ?
C1 C2 C3 C4 -0.1(2) . . . . ?
C2 C3 C4 S1 0.3(2) . . . . ?
C2 C3 C4 C5 179.78(18) . . . . ?
C3 C4 C5 O1 -164.68(19) . . . . ?
C3 C4 C5 N1 15.8(3) . . . . ?
C4 S1 C1 C2 0.23(16) . . . . ?
C5 N1 C6 S2 -177.01(14) . . . . ?
C5 N1 C6 N2 2.5(3) . . . . ?
C6 N1 C5 O1 -2.8(3) . . . . ?
C6 N1 C5 C4 176.70(16) . . . . ?
C6 N2 C7 C8 6.4(3) . . . . ?
C6 N2 C7 C12 -174.64(18) . . . . ?
C7 N2 C6 S2 -0.9(3) . . . . ?
C7 N2 C6 N1 179.72(16) . . . . ?
C7 C8 C9 C10 0.6(3) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C7 0.2(3) . . . . ?
C12 C7 C8 C9 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_ruc4
_database_code_depnum_ccdc_archive 'CCDC 1445387'
_audit_update_record             
;
2016-01-05 deposited with the CCDC.
2016-07-05 downloaded from the CCDC.
;
_audit_creation_date             2014-07-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H26 Cl2 N2 O Ru S2'
_chemical_formula_sum            'C23 H26 Cl2 N2 O Ru S2'
_chemical_formula_weight         582.55
_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'
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'
S S 0.1246 0.1234 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.035(2)
_cell_length_b                   10.272(2)
_cell_length_c                   12.006(2)
_cell_angle_alpha                79.528(2)
_cell_angle_beta                 80.344(2)
_cell_angle_gamma                85.730(2)
_cell_volume                     1198.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8753
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.570
_cell_measurement_theta_min      2.432
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    1.070
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0651 after correction.
The Ratio of minimum to maximum transmission is 0.8049.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13773
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.604
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4939
_reflns_number_total             5422
_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        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.638
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         5422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²+0.5095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0769
_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
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_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 0.74479(2) 0.64934(2) 0.54983(2) 0.01541(6) Uani 1 1 d . . . . .
Cl1 Cl 0.71812(6) 0.42006(5) 0.64705(4) 0.02239(12) Uani 1 1 d . . . . .
Cl2 Cl 0.91000(5) 0.67033(5) 0.67066(5) 0.02243(12) Uani 1 1 d . . . . .
S1 S 0.57303(5) 0.73035(5) 0.69071(4) 0.01979(12) Uani 1 1 d . . . . .
S2 S 0.88403(6) 0.37536(6) 1.09842(5) 0.02764(13) Uani 1 1 d . . . . .
O1 O 0.67055(18) 0.58044(16) 1.05044(13) 0.0282(4) Uani 1 1 d . . . . .
N1 N 0.67167(18) 0.56749(17) 0.86196(15) 0.0179(4) Uani 1 1 d . . . . .
H1 H 0.6904 0.5127 0.8124 0.021 Uiso 1 1 calc R U . . .
N2 N 0.55712(19) 0.75976(18) 0.90645(15) 0.0204(4) Uani 1 1 d . . . . .
H2 H 0.5680 0.7289 0.9779 0.024 Uiso 1 1 calc R U . . .
C1 C 0.6025(2) 0.6836(2) 0.82807(17) 0.0172(4) Uani 1 1 d . . . . .
C2 C 0.7153(2) 0.5279(2) 0.96730(17) 0.0184(4) Uani 1 1 d . . . . .
C3 C 0.8207(2) 0.4220(2) 0.97174(18) 0.0193(4) Uani 1 1 d . . . . .
C4 C 0.8856(2) 0.3535(2) 0.88841(19) 0.0248(5) Uani 1 1 d . . . . .
H4 H 0.8651 0.3656 0.8127 0.030 Uiso 1 1 calc R U . . .
C5 C 0.9869(3) 0.2626(3) 0.9293(2) 0.0344(6) Uani 1 1 d . . . . .
H5 H 1.0424 0.2067 0.8838 0.041 Uiso 1 1 calc R U . . .
C6 C 0.9964(3) 0.2640(3) 1.0407(2) 0.0347(6) Uani 1 1 d . . . . .
H6 H 1.0587 0.2090 1.0818 0.042 Uiso 1 1 calc R U . . .
C7 C 0.4917(2) 0.8886(2) 0.88238(17) 0.0192(4) Uani 1 1 d . . . . .
C8 C 0.5680(2) 0.9992(2) 0.83469(18) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.4977(3) 1.1224(2) 0.82038(19) 0.0264(5) Uani 1 1 d . . . . .
H9 H 0.5463 1.1997 0.7878 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3592(3) 1.1342(2) 0.85253(19) 0.0268(5) Uani 1 1 d . . . . .
H10 H 0.3139 1.2191 0.8420 0.032 Uiso 1 1 calc R U . . .
C11 C 0.2864(2) 1.0233(2) 0.8999(2) 0.0273(5) Uani 1 1 d . . . . .
H11 H 0.1911 1.0316 0.9219 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3532(2) 0.8996(2) 0.91502(19) 0.0236(5) Uani 1 1 d . . . . .
H12 H 0.3038 0.8227 0.9477 0.028 Uiso 1 1 calc R U . . .
C13 C 0.7190(2) 0.9883(3) 0.8019(2) 0.0331(6) Uani 1 1 d . . . . .
H13A H 0.7602 0.9526 0.8702 0.050 Uiso 1 1 calc R U . . .
H13B H 0.7529 1.0762 0.7684 0.050 Uiso 1 1 calc R U . . .
H13C H 0.7424 0.9289 0.7455 0.050 Uiso 1 1 calc R U . . .
C14 C 0.7916(2) 0.8321(2) 0.42728(18) 0.0221(4) Uani 1 1 d . . . . .
C15 C 0.8946(2) 0.7319(2) 0.40869(18) 0.0232(5) Uani 1 1 d . . . . .
H15 H 0.9857 0.7505 0.4095 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8669(2) 0.6066(2) 0.38912(18) 0.0256(5) Uani 1 1 d . . . . .
H16 H 0.9384 0.5425 0.3762 0.031 Uiso 1 1 calc R U . . .
C17 C 0.7311(3) 0.5765(2) 0.38878(18) 0.0270(5) Uani 1 1 d . . . . .
C18 C 0.6263(2) 0.6733(3) 0.40942(18) 0.0269(5) Uani 1 1 d . . . . .
H18 H 0.5349 0.6538 0.4107 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6570(2) 0.7990(2) 0.42824(18) 0.0249(5) Uani 1 1 d . . . . .
H19 H 0.5854 0.8628 0.4419 0.030 Uiso 1 1 calc R U . . .
C20 C 0.8284(3) 0.9660(2) 0.4447(2) 0.0334(6) Uani 1 1 d . . . . .
H20 H 0.8938 0.9511 0.5006 0.040 Uiso 1 1 calc R U . . .
C21 C 0.7086(4) 1.0502(3) 0.4923(3) 0.0507(8) Uani 1 1 d . . . . .
H21A H 0.6482 1.0754 0.4349 0.076 Uiso 1 1 calc R U . . .
H21B H 0.7412 1.1302 0.5105 0.076 Uiso 1 1 calc R U . . .
H21C H 0.6592 0.9992 0.5620 0.076 Uiso 1 1 calc R U . . .
C22 C 0.9013(3) 1.0386(3) 0.3302(3) 0.0469(8) Uani 1 1 d . . . . .
H22A H 0.9768 0.9819 0.3004 0.070 Uiso 1 1 calc R U . . .
H22B H 0.9360 1.1209 0.3420 0.070 Uiso 1 1 calc R U . . .
H22C H 0.8377 1.0594 0.2751 0.070 Uiso 1 1 calc R U . . .
C23 C 0.6994(3) 0.4419(3) 0.3711(2) 0.0443(8) Uani 1 1 d . . . . .
H23A H 0.7723 0.3778 0.3918 0.066 Uiso 1 1 calc R U . . .
H23B H 0.6913 0.4451 0.2905 0.066 Uiso 1 1 calc R U . . .
H23C H 0.6139 0.4150 0.4197 0.066 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 Cl1 2.4434(7) . ?
Ru1 Cl2 2.4235(6) . ?
Ru1 S1 2.4175(6) . ?
Ru1 C14 2.192(2) . ?
Ru1 C15 2.159(2) . ?
Ru1 C16 2.203(2) . ?
Ru1 C17 2.224(2) . ?
Ru1 C18 2.190(2) . ?
Ru1 C19 2.164(2) . ?
S1 C1 1.701(2) . ?
S2 C3 1.721(2) . ?
S2 C6 1.701(3) . ?
O1 C2 1.224(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.366(3) . ?
N1 C2 1.389(3) . ?
N2 H2 0.8800 . ?
N2 C1 1.332(3) . ?
N2 C7 1.436(3) . ?
C2 C3 1.460(3) . ?
C3 C4 1.375(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.416(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.360(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.396(3) . ?
C7 C12 1.382(3) . ?
C8 C9 1.399(3) . ?
C8 C13 1.501(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.389(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.422(3) . ?
C14 C19 1.416(3) . ?
C14 C20 1.509(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.405(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.420(3) . ?
C17 C18 1.415(4) . ?
C17 C23 1.501(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.415(4) . ?
C19 H19 0.9500 . ?
C20 H20 1.0000 . ?
C20 C21 1.521(4) . ?
C20 C22 1.534(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
Cl2 Ru1 Cl1 88.73(2) . . ?
S1 Ru1 Cl1 91.93(2) . . ?
S1 Ru1 Cl2 88.17(2) . . ?
C14 Ru1 Cl1 166.04(6) . . ?
C14 Ru1 Cl2 96.14(6) . . ?
C14 Ru1 S1 101.27(6) . . ?
C14 Ru1 C16 68.74(9) . . ?
C14 Ru1 C17 81.13(9) . . ?
C15 Ru1 Cl1 129.88(6) . . ?
C15 Ru1 Cl2 85.65(6) . . ?
C15 Ru1 S1 137.45(7) . . ?
C15 Ru1 C14 38.14(9) . . ?
C15 Ru1 C16 37.57(9) . . ?
C15 Ru1 C17 67.64(9) . . ?
C15 Ru1 C18 80.16(8) . . ?
C15 Ru1 C19 67.96(9) . . ?
C16 Ru1 Cl1 97.40(6) . . ?
C16 Ru1 Cl2 104.39(7) . . ?
C16 Ru1 S1 164.45(7) . . ?
C16 Ru1 C17 37.42(9) . . ?
C17 Ru1 Cl1 86.74(6) . . ?
C17 Ru1 Cl2 140.06(7) . . ?
C17 Ru1 S1 131.61(7) . . ?
C18 Ru1 Cl1 105.26(7) . . ?
C18 Ru1 Cl2 164.43(6) . . ?
C18 Ru1 S1 97.95(7) . . ?
C18 Ru1 C14 68.68(9) . . ?
C18 Ru1 C16 67.63(9) . . ?
C18 Ru1 C17 37.38(9) . . ?
C19 Ru1 Cl1 141.18(7) . . ?
C19 Ru1 Cl2 129.61(7) . . ?
C19 Ru1 S1 84.51(6) . . ?
C19 Ru1 C14 37.92(9) . . ?
C19 Ru1 C16 80.41(9) . . ?
C19 Ru1 C17 67.98(9) . . ?
C19 Ru1 C18 37.92(9) . . ?
C1 S1 Ru1 113.95(7) . . ?
C6 S2 C3 91.45(12) . . ?
C1 N1 H1 117.0 . . ?
C1 N1 C2 126.07(17) . . ?
C2 N1 H1 117.0 . . ?
C1 N2 H2 117.8 . . ?
C1 N2 C7 124.47(18) . . ?
C7 N2 H2 117.8 . . ?
N1 C1 S1 121.59(15) . . ?
N2 C1 S1 120.45(16) . . ?
N2 C1 N1 117.96(18) . . ?
O1 C2 N1 122.19(19) . . ?
O1 C2 C3 122.06(19) . . ?
N1 C2 C3 115.72(18) . . ?
C2 C3 S2 117.39(16) . . ?
C4 C3 S2 111.71(16) . . ?
C4 C3 C2 130.8(2) . . ?
C3 C4 H4 124.2 . . ?
C3 C4 C5 111.7(2) . . ?
C5 C4 H4 124.2 . . ?
C4 C5 H5 123.6 . . ?
C6 C5 C4 112.7(2) . . ?
C6 C5 H5 123.6 . . ?
S2 C6 H6 123.8 . . ?
C5 C6 S2 112.41(18) . . ?
C5 C6 H6 123.8 . . ?
C8 C7 N2 120.43(19) . . ?
C12 C7 N2 117.6(2) . . ?
C12 C7 C8 121.9(2) . . ?
C7 C8 C9 117.0(2) . . ?
C7 C8 C13 122.1(2) . . ?
C9 C8 C13 120.9(2) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(2) . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 119.7(2) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 Ru1 69.67(12) . . ?
C15 C14 C20 120.1(2) . . ?
C19 C14 Ru1 69.97(13) . . ?
C19 C14 C15 116.7(2) . . ?
C19 C14 C20 123.2(2) . . ?
C20 C14 Ru1 131.13(16) . . ?
Ru1 C15 H15 128.7 . . ?
C14 C15 Ru1 72.18(12) . . ?
C14 C15 H15 118.7 . . ?
C16 C15 Ru1 72.89(12) . . ?
C16 C15 C14 122.7(2) . . ?
C16 C15 H15 118.7 . . ?
Ru1 C16 H16 130.6 . . ?
C15 C16 Ru1 69.54(12) . . ?
C15 C16 H16 120.3 . . ?
C15 C16 C17 119.5(2) . . ?
C17 C16 Ru1 72.12(12) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 Ru1 70.46(13) . . ?
C16 C17 C23 120.1(3) . . ?
C18 C17 Ru1 69.97(12) . . ?
C18 C17 C16 119.1(2) . . ?
C18 C17 C23 120.7(2) . . ?
C23 C17 Ru1 129.92(17) . . ?
Ru1 C18 H18 129.9 . . ?
C17 C18 Ru1 72.65(13) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 Ru1 70.08(12) . . ?
C19 C18 C17 120.3(2) . . ?
C19 C18 H18 119.9 . . ?
Ru1 C19 H19 129.2 . . ?
C14 C19 Ru1 72.11(12) . . ?
C14 C19 H19 119.1 . . ?
C18 C19 Ru1 72.01(13) . . ?
C18 C19 C14 121.7(2) . . ?
C18 C19 H19 119.1 . . ?
C14 C20 H20 107.8 . . ?
C14 C20 C21 114.0(2) . . ?
C14 C20 C22 108.3(2) . . ?
C21 C20 H20 107.8 . . ?
C21 C20 C22 110.8(2) . . ?
C22 C20 H20 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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 Cl1 0.88 2.32 3.1748(18) 163.6 .
N2 H2 O1 0.88 1.93 2.621(2) 134.0 .
C4 H4 Cl1 0.95 2.63 3.526(2) 158.2 .

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 S1 C1 N1 -29.7(2) . . . . ?
Ru1 S1 C1 N2 150.92(15) . . . . ?
Ru1 C14 C15 C16 55.02(19) . . . . ?
Ru1 C14 C19 C18 -54.49(19) . . . . ?
Ru1 C14 C20 C21 -77.2(3) . . . . ?
Ru1 C14 C20 C22 158.8(2) . . . . ?
Ru1 C15 C16 C17 54.03(18) . . . . ?
Ru1 C16 C17 C18 52.16(18) . . . . ?
Ru1 C16 C17 C23 -125.5(2) . . . . ?
Ru1 C17 C18 C19 53.42(18) . . . . ?
Ru1 C18 C19 C14 54.54(19) . . . . ?
S2 C3 C4 C5 0.2(3) . . . . ?
O1 C2 C3 S2 -1.5(3) . . . . ?
O1 C2 C3 C4 -178.3(2) . . . . ?
N1 C2 C3 S2 176.78(15) . . . . ?
N1 C2 C3 C4 0.0(4) . . . . ?
N2 C7 C8 C9 -176.14(19) . . . . ?
N2 C7 C8 C13 2.7(3) . . . . ?
N2 C7 C12 C11 176.2(2) . . . . ?
C1 N1 C2 O1 16.4(3) . . . . ?
C1 N1 C2 C3 -161.9(2) . . . . ?
C1 N2 C7 C8 -79.1(3) . . . . ?
C1 N2 C7 C12 105.0(2) . . . . ?
C2 N1 C1 S1 171.65(17) . . . . ?
C2 N1 C1 N2 -8.9(3) . . . . ?
C2 C3 C4 C5 177.1(2) . . . . ?
C3 S2 C6 C5 0.3(2) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 S2 -0.3(3) . . . . ?
C6 S2 C3 C2 -177.65(19) . . . . ?
C6 S2 C3 C4 -0.3(2) . . . . ?
C7 N2 C1 S1 -5.4(3) . . . . ?
C7 N2 C1 N1 175.2(2) . . . . ?
C7 C8 C9 C10 0.3(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
C12 C7 C8 C13 178.4(2) . . . . ?
C13 C8 C9 C10 -178.6(2) . . . . ?
C14 C15 C16 Ru1 -54.71(19) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C14 C19 Ru1 53.29(17) . . . . ?
C15 C14 C19 C18 -1.2(3) . . . . ?
C15 C14 C20 C21 -165.7(2) . . . . ?
C15 C14 C20 C22 70.4(3) . . . . ?
C15 C16 C17 Ru1 -52.83(18) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C15 C16 C17 C23 -178.4(2) . . . . ?
C16 C17 C18 Ru1 -52.38(18) . . . . ?
C16 C17 C18 C19 1.0(3) . . . . ?
C17 C18 C19 Ru1 -54.61(19) . . . . ?
C17 C18 C19 C14 -0.1(3) . . . . ?
C19 C14 C15 Ru1 -53.44(17) . . . . ?
C19 C14 C15 C16 1.6(3) . . . . ?
C19 C14 C20 C21 14.3(3) . . . . ?
C19 C14 C20 C22 -109.6(3) . . . . ?
C20 C14 C15 Ru1 126.6(2) . . . . ?
C20 C14 C15 C16 -178.4(2) . . . . ?
C20 C14 C19 Ru1 -126.7(2) . . . . ?
C20 C14 C19 C18 178.8(2) . . . . ?
C23 C17 C18 Ru1 125.3(2) . . . . ?
C23 C17 C18 C19 178.7(2) . . . . ?

