# Electronic Supplementary Material (ESI) for RSC Advances.
# 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).
# 
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# 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 
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data_ruptdpa
_database_code_depnum_ccdc_archive 'CCDC 1458027'
_audit_update_record             
;
2016-03-07 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_audit_creation_date             2015-03-04
_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 H30 Cl2 N2 O3 Ru S2'
_chemical_formula_sum            'C26 H30 Cl2 N2 O3 Ru S2'
_chemical_formula_weight         654.61
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.408(3)
_cell_length_b                   13.270(5)
_cell_length_c                   18.477(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2797.3(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9972
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.497
_cell_measurement_theta_min      2.204
_shelx_estimated_absorpt_T_max   0.807
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    0.932
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.1044 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.8278.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32747
_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         27.554
_diffrn_reflns_theta_min         1.889
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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         0.780
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                6067
_reflns_number_total             6363
_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         0.743
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 2575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.002(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6363
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.051
_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)+(0.0281P)²+1.2862P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0579
_refine_ls_wR_factor_ref         0.0593
_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:
 C2(H2A), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15),
 C16(H16), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_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 0.49659(2) 0.52147(2) 0.70028(2) 0.01532(7) Uani 1 1 d . . . . .
Cl1 Cl 0.46194(7) 0.48710(7) 0.57319(4) 0.02601(18) Uani 1 1 d . . . . .
Cl2 Cl 0.37845(7) 0.67139(6) 0.68310(4) 0.01984(16) Uani 1 1 d . . . . .
S1 S 0.32593(7) 0.42427(6) 0.73372(5) 0.02171(18) Uani 1 1 d . . . . .
S2 S 0.00719(9) 0.68035(6) 0.49583(4) 0.02446(17) Uani 1 1 d . . . . .
O1 O -0.1138(2) 0.4549(2) 0.78052(14) 0.0314(6) Uani 1 1 d . . . . .
O2 O -0.0560(2) 0.3828(2) 0.88439(14) 0.0344(6) Uani 1 1 d . . . . .
O3 O 0.0000(2) 0.54194(18) 0.61856(12) 0.0278(5) Uani 1 1 d . . . . .
N1 N 0.0954(2) 0.4339(2) 0.72113(15) 0.0203(6) Uani 1 1 d . . . . .
H1 H 0.0321 0.4507 0.6967 0.024 Uiso 1 1 calc R . . . .
N2 N 0.1975(2) 0.5112(2) 0.62908(14) 0.0202(6) Uani 1 1 d . . . . .
H2 H 0.2652 0.5183 0.6068 0.024 Uiso 1 1 calc R . . . .
C1 C 0.1975(3) 0.4578(2) 0.69259(18) 0.0188(6) Uani 1 1 d . . . . .
C2 C 0.0789(3) 0.3824(3) 0.78954(18) 0.0203(7) Uani 1 1 d . . . . .
H2A H 0.1390 0.4071 0.8247 0.024 Uiso 1 1 calc R . . . .
C3 C 0.0914(3) 0.2667(3) 0.78182(19) 0.0230(7) Uani 1 1 d . . . . .
H3A H 0.1751 0.2503 0.7741 0.028 Uiso 1 1 calc R . . . .
H3B H 0.0667 0.2347 0.8277 0.028 Uiso 1 1 calc R . . . .
C4 C 0.0208(3) 0.2221(2) 0.72083(19) 0.0241(7) Uani 1 1 d . . . . .
C5 C 0.0710(4) 0.2080(3) 0.6531(2) 0.0363(9) Uani 1 1 d . . . . .
H5 H 0.1498 0.2283 0.6449 0.044 Uiso 1 1 calc R . . . .
C6 C 0.0070(5) 0.1643(3) 0.5971(2) 0.0428(10) Uani 1 1 d . . . . .
H6 H 0.0424 0.1550 0.5510 0.051 Uiso 1 1 calc R . . . .
C7 C -0.1071(4) 0.1345(3) 0.6080(2) 0.0386(10) Uani 1 1 d . . . . .
H7 H -0.1502 0.1039 0.5698 0.046 Uiso 1 1 calc R . . . .
C8 C -0.1587(4) 0.1495(3) 0.6752(2) 0.0335(9) Uani 1 1 d . . . . .
H8 H -0.2377 0.1295 0.6831 0.040 Uiso 1 1 calc R . . . .
C9 C -0.0951(3) 0.1935(3) 0.7309(2) 0.0262(8) Uani 1 1 d . . . . .
H9 H -0.1314 0.2041 0.7766 0.031 Uiso 1 1 calc R . . . .
C10 C -0.0418(3) 0.4121(3) 0.81651(18) 0.0215(7) Uani 1 1 d . . . . .
C11 C -0.1687(4) 0.4058(4) 0.9165(3) 0.0481(12) Uani 1 1 d . . . . .
H11A H -0.2281 0.3596 0.8974 0.072 Uiso 1 1 calc GR . . . .
H11B H -0.1906 0.4753 0.9048 0.072 Uiso 1 1 calc GR . . . .
H11C H -0.1637 0.3981 0.9692 0.072 Uiso 1 1 calc GR . . . .
C12 C 0.1005(3) 0.5552(3) 0.59688(17) 0.0196(7) Uani 1 1 d . . . . .
C13 C 0.1262(3) 0.6206(3) 0.53531(17) 0.0195(7) Uani 1 1 d . . . . .
C14 C 0.2284(3) 0.6434(3) 0.50069(18) 0.0252(8) Uani 1 1 d . . . . .
H14 H 0.3030 0.6181 0.5146 0.030 Uiso 1 1 calc R . . . .
C15 C 0.2100(4) 0.7092(3) 0.4418(2) 0.0315(9) Uani 1 1 d . . . . .
H15 H 0.2712 0.7327 0.4112 0.038 Uiso 1 1 calc R . . . .
C16 C 0.0957(3) 0.7354(3) 0.43333(19) 0.0297(8) Uani 1 1 d . . . . .
H16 H 0.0683 0.7795 0.3966 0.036 Uiso 1 1 calc R . . . .
C17 C 0.5705(3) 0.5702(3) 0.80448(19) 0.0254(7) Uani 1 1 d . . . . .
C18 C 0.6269(3) 0.6207(3) 0.7461(2) 0.0248(8) Uani 1 1 d . . . . .
H18 H 0.6285 0.6923 0.7456 0.030 Uiso 1 1 calc R . . . .
C19 C 0.6800(3) 0.5681(3) 0.68953(19) 0.0217(7) Uani 1 1 d . . . . .
H19 H 0.7193 0.6047 0.6526 0.026 Uiso 1 1 calc R . . . .
C20 C 0.6768(3) 0.4619(3) 0.68566(19) 0.0242(7) Uani 1 1 d . . . . .
C21 C 0.6200(3) 0.4105(3) 0.7424(2) 0.0261(8) Uani 1 1 d . . . . .
H21 H 0.6164 0.3390 0.7416 0.031 Uiso 1 1 calc R . . . .
C22 C 0.5680(3) 0.4639(3) 0.8006(2) 0.0281(8) Uani 1 1 d . . . . .
H22 H 0.5304 0.4271 0.8380 0.034 Uiso 1 1 calc R . . . .
C23 C 0.5126(4) 0.6354(3) 0.8634(2) 0.0396(9) Uani 1 1 d . . . . .
H23 H 0.4625 0.6862 0.8381 0.047 Uiso 1 1 calc R . . . .
C24 C 0.6063(5) 0.6937(4) 0.9053(3) 0.0552(14) Uani 1 1 d . . . . .
H24A H 0.6555 0.6463 0.9323 0.083 Uiso 1 1 calc GR . . . .
H24B H 0.5684 0.7404 0.9390 0.083 Uiso 1 1 calc GR . . . .
H24C H 0.6551 0.7318 0.8712 0.083 Uiso 1 1 calc GR . . . .
C25 C 0.4342(4) 0.5761(4) 0.9123(3) 0.0488(12) Uani 1 1 d . . . . .
H25A H 0.3791 0.5365 0.8832 0.073 Uiso 1 1 calc GR . . . .
H25B H 0.3905 0.6222 0.9437 0.073 Uiso 1 1 calc GR . . . .
H25C H 0.4817 0.5306 0.9422 0.073 Uiso 1 1 calc GR . . . .
C26 C 0.7293(4) 0.4068(3) 0.6229(2) 0.0373(10) Uani 1 1 d . . . . .
H26A H 0.6858 0.3441 0.6146 0.056 Uiso 1 1 calc GR . . . .
H26B H 0.8114 0.3910 0.6335 0.056 Uiso 1 1 calc GR . . . .
H26C H 0.7250 0.4491 0.5795 0.056 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 Cl1 2.4247(10) . ?
Ru1 Cl2 2.4239(10) . ?
Ru1 S1 2.4157(9) . ?
Ru1 C17 2.199(3) . ?
Ru1 C18 2.159(3) . ?
Ru1 C19 2.191(3) . ?
Ru1 C20 2.219(3) . ?
Ru1 C21 2.180(3) . ?
Ru1 C22 2.163(3) . ?
S1 C1 1.710(3) . ?
S2 C13 1.733(3) . ?
S2 C16 1.699(4) . ?
O1 C10 1.200(4) . ?
O2 C10 1.323(4) . ?
O2 C11 1.449(5) . ?
O3 C12 1.228(4) . ?
N1 H1 0.8800 . ?
N1 C1 1.317(4) . ?
N1 C2 1.450(4) . ?
N2 H2 0.8800 . ?
N2 C1 1.371(4) . ?
N2 C12 1.385(4) . ?
C2 H2A 1.0000 . ?
C2 C3 1.548(5) . ?
C2 C10 1.517(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.506(5) . ?
C4 C5 1.389(5) . ?
C4 C9 1.388(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.375(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(5) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.461(5) . ?
C13 C14 1.364(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.411(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.358(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.424(5) . ?
C17 C22 1.413(5) . ?
C17 C23 1.538(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.411(5) . ?
C20 C21 1.408(5) . ?
C20 C26 1.496(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.418(6) . ?
C22 H22 0.9500 . ?
C23 H23 1.0000 . ?
C23 C24 1.530(6) . ?
C23 C25 1.496(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
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 86.38(3) . . ?
S1 Ru1 Cl1 90.91(3) . . ?
S1 Ru1 Cl2 91.36(4) . . ?
C17 Ru1 Cl1 164.96(9) . . ?
C17 Ru1 Cl2 94.95(10) . . ?
C17 Ru1 S1 104.02(10) . . ?
C17 Ru1 C20 81.74(13) . . ?
C18 Ru1 Cl1 127.35(10) . . ?
C18 Ru1 Cl2 86.19(10) . . ?
C18 Ru1 S1 141.30(10) . . ?
C18 Ru1 C17 38.12(13) . . ?
C18 Ru1 C19 37.41(13) . . ?
C18 Ru1 C20 68.10(14) . . ?
C18 Ru1 C21 80.07(13) . . ?
C18 Ru1 C22 67.69(14) . . ?
C19 Ru1 Cl1 96.94(9) . . ?
C19 Ru1 Cl2 106.70(9) . . ?
C19 Ru1 S1 160.67(9) . . ?
C19 Ru1 C17 68.30(13) . . ?
C19 Ru1 C20 37.32(12) . . ?
C20 Ru1 Cl1 88.06(9) . . ?
C20 Ru1 Cl2 142.33(9) . . ?
C20 Ru1 S1 125.99(10) . . ?
C21 Ru1 Cl1 108.88(11) . . ?
C21 Ru1 Cl2 163.74(10) . . ?
C21 Ru1 S1 93.93(10) . . ?
C21 Ru1 C17 68.84(14) . . ?
C21 Ru1 C19 66.82(13) . . ?
C21 Ru1 C20 37.32(13) . . ?
C22 Ru1 Cl1 145.53(11) . . ?
C22 Ru1 Cl2 127.70(11) . . ?
C22 Ru1 S1 84.03(9) . . ?
C22 Ru1 C17 37.80(14) . . ?
C22 Ru1 C19 79.50(13) . . ?
C22 Ru1 C20 68.26(13) . . ?
C22 Ru1 C21 38.09(15) . . ?
C1 S1 Ru1 116.00(11) . . ?
C16 S2 C13 90.98(18) . . ?
C10 O2 C11 115.8(3) . . ?
C1 N1 H1 117.4 . . ?
C1 N1 C2 125.2(3) . . ?
C2 N1 H1 117.4 . . ?
C1 N2 H2 117.1 . . ?
C1 N2 C12 125.8(3) . . ?
C12 N2 H2 117.1 . . ?
N1 C1 S1 121.2(2) . . ?
N1 C1 N2 117.9(3) . . ?
N2 C1 S1 121.0(2) . . ?
N1 C2 H2A 108.8 . . ?
N1 C2 C3 112.1(3) . . ?
N1 C2 C10 106.3(3) . . ?
C3 C2 H2A 108.8 . . ?
C10 C2 H2A 108.8 . . ?
C10 C2 C3 111.8(3) . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.2(3) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C5 C4 C3 120.5(3) . . ?
C9 C4 C3 121.1(3) . . ?
C9 C4 C5 118.5(3) . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.5(4) . . ?
C7 C6 H6 119.8 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.4(4) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.5 . . ?
C8 C9 C4 120.9(4) . . ?
C8 C9 H9 119.5 . . ?
O1 C10 O2 125.5(3) . . ?
O1 C10 C2 124.2(3) . . ?
O2 C10 C2 110.2(3) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 N2 123.1(3) . . ?
O3 C12 C13 121.8(3) . . ?
N2 C12 C13 115.1(3) . . ?
C12 C13 S2 116.3(2) . . ?
C14 C13 S2 111.8(3) . . ?
C14 C13 C12 131.9(3) . . ?
C13 C14 H14 124.1 . . ?
C13 C14 C15 111.8(3) . . ?
C15 C14 H14 124.1 . . ?
C14 C15 H15 123.5 . . ?
C16 C15 C14 112.9(3) . . ?
C16 C15 H15 123.5 . . ?
S2 C16 H16 123.7 . . ?
C15 C16 S2 112.5(3) . . ?
C15 C16 H16 123.7 . . ?
C18 C17 Ru1 69.4(2) . . ?
C18 C17 C23 117.7(3) . . ?
C22 C17 Ru1 69.7(2) . . ?
C22 C17 C18 116.1(3) . . ?
C22 C17 C23 126.1(3) . . ?
C23 C17 Ru1 128.3(2) . . ?
Ru1 C18 H18 128.3 . . ?
C17 C18 Ru1 72.45(19) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 Ru1 72.52(19) . . ?
C19 C18 C17 121.9(3) . . ?
C19 C18 H18 119.1 . . ?
Ru1 C19 H19 131.4 . . ?
C18 C19 Ru1 70.07(19) . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.8(3) . . ?
C20 C19 Ru1 72.4(2) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 Ru1 70.27(19) . . ?
C19 C20 C26 121.1(3) . . ?
C21 C20 Ru1 69.86(19) . . ?
C21 C20 C19 117.3(3) . . ?
C21 C20 C26 121.6(3) . . ?
C26 C20 Ru1 129.8(3) . . ?
Ru1 C21 H21 129.9 . . ?
C20 C21 Ru1 72.82(19) . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(3) . . ?
C22 C21 Ru1 70.3(2) . . ?
C22 C21 H21 119.5 . . ?
Ru1 C22 H22 129.5 . . ?
C17 C22 Ru1 72.5(2) . . ?
C17 C22 C21 122.0(3) . . ?
C17 C22 H22 119.0 . . ?
C21 C22 Ru1 71.6(2) . . ?
C21 C22 H22 119.0 . . ?
C17 C23 H23 107.1 . . ?
C24 C23 C17 110.0(3) . . ?
C24 C23 H23 107.1 . . ?
C25 C23 C17 112.9(4) . . ?
C25 C23 H23 107.1 . . ?
C25 C23 C24 112.2(4) . . ?
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 . . ?
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 . . ?
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 . . ?

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 O3 0.88 1.92 2.613(3) 134.5 .
N2 H2 Cl1 0.88 2.37 3.204(3) 159.6 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1 S1 C1 N1 -158.7(2) . . . . ?
Ru1 S1 C1 N2 20.7(3) . . . . ?
Ru1 C17 C18 C19 -55.4(3) . . . . ?
Ru1 C17 C22 C21 54.0(3) . . . . ?
Ru1 C17 C23 C24 -151.4(3) . . . . ?
Ru1 C17 C23 C25 82.4(4) . . . . ?
Ru1 C18 C19 C20 -52.9(3) . . . . ?
Ru1 C19 C20 C21 -53.4(3) . . . . ?
Ru1 C19 C20 C26 125.2(3) . . . . ?
Ru1 C20 C21 C22 -53.3(3) . . . . ?
Ru1 C21 C22 C17 -54.4(3) . . . . ?
S2 C13 C14 C15 -0.2(4) . . . . ?
O3 C12 C13 S2 1.3(4) . . . . ?
O3 C12 C13 C14 -177.3(4) . . . . ?
N1 C2 C3 C4 -49.3(4) . . . . ?
N1 C2 C10 O1 11.9(5) . . . . ?
N1 C2 C10 O2 -169.1(3) . . . . ?
N2 C12 C13 S2 -177.8(2) . . . . ?
N2 C12 C13 C14 3.6(6) . . . . ?
C1 N1 C2 C3 -82.6(4) . . . . ?
C1 N1 C2 C10 154.9(3) . . . . ?
C1 N2 C12 O3 -7.8(5) . . . . ?
C1 N2 C12 C13 171.2(3) . . . . ?
C2 N1 C1 S1 2.7(5) . . . . ?
C2 N1 C1 N2 -176.7(3) . . . . ?
C2 C3 C4 C5 93.5(4) . . . . ?
C2 C3 C4 C9 -87.1(4) . . . . ?
C3 C2 C10 O1 -110.7(4) . . . . ?
C3 C2 C10 O2 68.3(4) . . . . ?
C3 C4 C5 C6 178.3(4) . . . . ?
C3 C4 C9 C8 -177.9(3) . . . . ?
C4 C5 C6 C7 0.0(7) . . . . ?
C5 C4 C9 C8 1.5(5) . . . . ?
C5 C6 C7 C8 0.8(7) . . . . ?
C6 C7 C8 C9 -0.5(6) . . . . ?
C7 C8 C9 C4 -0.7(6) . . . . ?
C9 C4 C5 C6 -1.2(6) . . . . ?
C10 C2 C3 C4 70.0(4) . . . . ?
C11 O2 C10 O1 -0.3(6) . . . . ?
C11 O2 C10 C2 -179.4(3) . . . . ?
C12 N2 C1 S1 -169.7(3) . . . . ?
C12 N2 C1 N1 9.7(5) . . . . ?
C12 C13 C14 C15 178.4(4) . . . . ?
C13 S2 C16 C15 0.3(3) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C14 C15 C16 S2 -0.5(5) . . . . ?
C16 S2 C13 C12 -178.9(3) . . . . ?
C16 S2 C13 C14 0.0(3) . . . . ?
C17 C18 C19 Ru1 55.4(3) . . . . ?
C17 C18 C19 C20 2.4(5) . . . . ?
C18 C17 C22 Ru1 -53.3(3) . . . . ?
C18 C17 C22 C21 0.8(5) . . . . ?
C18 C17 C23 C24 -66.6(5) . . . . ?
C18 C17 C23 C25 167.2(3) . . . . ?
C18 C19 C20 Ru1 51.9(3) . . . . ?
C18 C19 C20 C21 -1.5(5) . . . . ?
C18 C19 C20 C26 177.2(3) . . . . ?
C19 C20 C21 Ru1 53.6(3) . . . . ?
C19 C20 C21 C22 0.3(5) . . . . ?
C20 C21 C22 Ru1 54.5(3) . . . . ?
C20 C21 C22 C17 0.1(5) . . . . ?
C22 C17 C18 Ru1 53.4(3) . . . . ?
C22 C17 C18 C19 -2.0(5) . . . . ?
C22 C17 C23 C24 116.9(4) . . . . ?
C22 C17 C23 C25 -9.3(5) . . . . ?
C23 C17 C18 Ru1 -123.4(3) . . . . ?
C23 C17 C18 C19 -178.8(3) . . . . ?
C23 C17 C22 Ru1 123.3(3) . . . . ?
C23 C17 C22 C21 177.3(3) . . . . ?
C26 C20 C21 Ru1 -125.0(3) . . . . ?
C26 C20 C21 C22 -178.4(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_rupflpa
_database_code_depnum_ccdc_archive 'CCDC 1458028'
_audit_update_record             
;
2016-03-07 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_audit_creation_date             2015-03-04
_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 H30 Cl2 N2 O4 Ru S'
_chemical_formula_sum            'C26 H30 Cl2 N2 O4 Ru S'
_chemical_formula_weight         638.55
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.398(2)
_cell_length_b                   13.064(3)
_cell_length_c                   18.578(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2766.2(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9981
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.428
_cell_measurement_theta_min      2.197
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.733
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6628
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014) was used for absorption correction.
wR2(int) was 0.0635 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.8889.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32418
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         1.906
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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         0.781
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                6038
_reflns_number_total             6329
_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         1.124
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 2588 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         6329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+1.7337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0727
_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:
 C7(H7), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_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 0.50422(2) 0.51653(2) 0.30280(2) 0.01789(8) Uani 1 1 d . . . . .
Cl1 Cl 0.46793(9) 0.48078(9) 0.42908(5) 0.0335(2) Uani 1 1 d . . . . .
Cl2 Cl 0.39099(8) 0.67212(7) 0.31967(5) 0.02335(19) Uani 1 1 d . . . . .
S1 S 0.32982(9) 0.42184(8) 0.26941(6) 0.0268(2) Uani 1 1 d . . . . .
O1 O 0.0095(3) 0.5553(2) 0.38550(16) 0.0346(6) Uani 1 1 d . . . . .
O2 O 0.0560(3) 0.6793(3) 0.50020(16) 0.0388(8) Uani 1 1 d . . . . .
O3 O -0.1083(3) 0.4660(3) 0.22017(17) 0.0365(7) Uani 1 1 d . . . . .
O4 O -0.0529(3) 0.3843(3) 0.11927(18) 0.0409(8) Uani 1 1 d . . . . .
N1 N 0.2053(3) 0.5144(3) 0.37371(17) 0.0260(7) Uani 1 1 d . . . . .
H1 H 0.2734 0.5180 0.3960 0.031 Uiso 1 1 calc R . . . .
N2 N 0.0993(3) 0.4388(2) 0.28213(18) 0.0244(7) Uani 1 1 d . . . . .
H2 H 0.0366 0.4585 0.3060 0.029 Uiso 1 1 calc R . . . .
C1 C 0.2025(3) 0.4601(3) 0.3104(2) 0.0233(8) Uani 1 1 d . . . . .
C2 C 0.1117(4) 0.5638(3) 0.4058(2) 0.0278(9) Uani 1 1 d . . . . .
C3 C 0.1457(4) 0.6274(3) 0.4674(2) 0.0306(9) Uani 1 1 d . . . . .
C4 C 0.2488(5) 0.6482(4) 0.4998(3) 0.0473(14) Uani 1 1 d . . . . .
H4 H 0.3241 0.6233 0.4865 0.057 Uiso 1 1 calc R . . . .
C5 C 0.2222(6) 0.7151(5) 0.5578(3) 0.0608(18) Uani 1 1 d . . . . .
H5 H 0.2760 0.7425 0.5918 0.073 Uiso 1 1 calc R . . . .
C6 C 0.1053(6) 0.7320(4) 0.5552(3) 0.0489(14) Uani 1 1 d . . . . .
H6 H 0.0634 0.7751 0.5875 0.059 Uiso 1 1 calc R . . . .
C7 C 0.0811(4) 0.3853(3) 0.2144(2) 0.0255(8) Uani 1 1 d . . . . .
H7 H 0.1427 0.4077 0.1794 0.031 Uiso 1 1 calc R . . . .
C8 C 0.0886(4) 0.2675(3) 0.2234(2) 0.0275(8) Uani 1 1 d . . . . .
H8A H 0.0645 0.2347 0.1777 0.033 Uiso 1 1 calc R . . . .
H8B H 0.1713 0.2484 0.2326 0.033 Uiso 1 1 calc R . . . .
C9 C 0.0134(4) 0.2257(3) 0.2835(2) 0.0264(8) Uani 1 1 d . . . . .
C10 C 0.0588(4) 0.2135(4) 0.3522(3) 0.0407(11) Uani 1 1 d . . . . .
H10 H 0.1368 0.2353 0.3619 0.049 Uiso 1 1 calc R . . . .
C11 C -0.0075(6) 0.1701(4) 0.4072(2) 0.0472(12) Uani 1 1 d . . . . .
H11 H 0.0253 0.1615 0.4539 0.057 Uiso 1 1 calc R . . . .
C12 C -0.1213(5) 0.1395(4) 0.3934(3) 0.0425(12) Uani 1 1 d . . . . .
H12 H -0.1669 0.1095 0.4307 0.051 Uiso 1 1 calc R . . . .
C13 C -0.1691(4) 0.1522(3) 0.3260(3) 0.0352(10) Uani 1 1 d . . . . .
H13 H -0.2475 0.1310 0.3170 0.042 Uiso 1 1 calc R . . . .
C14 C -0.1029(4) 0.1959(3) 0.2708(2) 0.0271(8) Uani 1 1 d . . . . .
H14 H -0.1367 0.2055 0.2246 0.032 Uiso 1 1 calc R . . . .
C15 C -0.0385(3) 0.4182(3) 0.1863(2) 0.0282(8) Uani 1 1 d . . . . .
C16 C -0.1630(6) 0.4114(6) 0.0867(3) 0.0662(18) Uani 1 1 d . . . . .
H16A H -0.1541 0.4129 0.0342 0.099 Uiso 1 1 calc GR . . . .
H16B H -0.1873 0.4791 0.1038 0.099 Uiso 1 1 calc GR . . . .
H16C H -0.2226 0.3607 0.0999 0.099 Uiso 1 1 calc GR . . . .
C17 C 0.5773(3) 0.5567(3) 0.1967(2) 0.0306(9) Uani 1 1 d . . . . .
C18 C 0.6320(4) 0.6136(3) 0.2516(3) 0.0326(10) Uani 1 1 d . . . . .
H18 H 0.6319 0.6862 0.2479 0.039 Uiso 1 1 calc R . . . .
C19 C 0.6862(3) 0.5690(3) 0.3112(3) 0.0300(9) Uani 1 1 d . . . . .
H19 H 0.7231 0.6113 0.3461 0.036 Uiso 1 1 calc R . . . .
C20 C 0.6869(3) 0.4606(3) 0.3201(2) 0.0259(8) Uani 1 1 d . . . . .
C21 C 0.6314(4) 0.4011(3) 0.2671(2) 0.0257(9) Uani 1 1 d . . . . .
H21 H 0.6302 0.3287 0.2717 0.031 Uiso 1 1 calc R . . . .
C22 C 0.5772(3) 0.4482(3) 0.2067(2) 0.0288(9) Uani 1 1 d . . . . .
H22 H 0.5396 0.4062 0.1719 0.035 Uiso 1 1 calc R . . . .
C23 C 0.5203(4) 0.6159(6) 0.1346(3) 0.0568(16) Uani 1 1 d . . . . .
H23 H 0.4666 0.6673 0.1571 0.068 Uiso 1 1 calc R . . . .
C24 C 0.6142(6) 0.6771(6) 0.0933(4) 0.072(2) Uani 1 1 d . . . . .
H24A H 0.6642 0.7138 0.1276 0.109 Uiso 1 1 calc GR . . . .
H24B H 0.5758 0.7264 0.0612 0.109 Uiso 1 1 calc GR . . . .
H24C H 0.6623 0.6301 0.0647 0.109 Uiso 1 1 calc GR . . . .
C25 C 0.4482(6) 0.5517(5) 0.0898(4) 0.0671(18) Uani 1 1 d . . . . .
H25A H 0.4983 0.5067 0.0608 0.101 Uiso 1 1 calc GR . . . .
H25B H 0.4005 0.5945 0.0578 0.101 Uiso 1 1 calc GR . . . .
H25C H 0.3966 0.5100 0.1201 0.101 Uiso 1 1 calc GR . . . .
C26 C 0.7409(4) 0.4127(4) 0.3855(3) 0.0430(12) Uani 1 1 d . . . . .
H26A H 0.7421 0.4625 0.4249 0.064 Uiso 1 1 calc GR . . . .
H26B H 0.8214 0.3913 0.3745 0.064 Uiso 1 1 calc GR . . . .
H26C H 0.6947 0.3529 0.3999 0.064 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 Cl1 2.4275(11) . ?
Ru1 Cl2 2.4280(10) . ?
Ru1 S1 2.4221(11) . ?
Ru1 C17 2.204(4) . ?
Ru1 C18 2.153(4) . ?
Ru1 C19 2.191(4) . ?
Ru1 C20 2.230(4) . ?
Ru1 C21 2.194(4) . ?
Ru1 C22 2.162(4) . ?
S1 C1 1.714(4) . ?
O1 C2 1.229(5) . ?
O2 C3 1.369(5) . ?
O2 C6 1.354(6) . ?
O3 C15 1.191(5) . ?
O4 C15 1.331(5) . ?
O4 C16 1.438(7) . ?
N1 H1 0.8800 . ?
N1 C1 1.373(5) . ?
N1 C2 1.383(5) . ?
N2 H2 0.8800 . ?
N2 C1 1.318(5) . ?
N2 C7 1.454(5) . ?
C2 C3 1.466(6) . ?
C3 C4 1.348(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.420(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.352(9) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.550(5) . ?
C7 C15 1.523(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.510(6) . ?
C9 C10 1.386(6) . ?
C9 C14 1.401(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(7) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.375(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.396(6) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.409(6) . ?
C17 C22 1.429(6) . ?
C17 C23 1.533(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.395(6) . ?
C19 H19 0.9500 . ?
C19 C20 1.426(6) . ?
C20 C21 1.404(6) . ?
C20 C26 1.499(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.421(6) . ?
C22 H22 0.9500 . ?
C23 H23 1.0000 . ?
C23 C24 1.541(8) . ?
C23 C25 1.440(9) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
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
Cl1 Ru1 Cl2 86.90(3) . . ?
S1 Ru1 Cl1 90.54(4) . . ?
S1 Ru1 Cl2 91.40(4) . . ?
C17 Ru1 Cl1 167.13(11) . . ?
C17 Ru1 Cl2 96.73(12) . . ?
C17 Ru1 S1 101.68(12) . . ?
C17 Ru1 C20 81.59(15) . . ?
C18 Ru1 Cl1 130.95(13) . . ?
C18 Ru1 Cl2 85.59(12) . . ?
C18 Ru1 S1 138.00(13) . . ?
C18 Ru1 C17 37.73(17) . . ?
C18 Ru1 C19 37.46(17) . . ?
C18 Ru1 C20 67.97(17) . . ?
C18 Ru1 C21 79.89(16) . . ?
C18 Ru1 C22 67.57(17) . . ?
C19 Ru1 Cl1 98.79(13) . . ?
C19 Ru1 Cl2 103.42(11) . . ?
C19 Ru1 S1 162.82(11) . . ?
C19 Ru1 C17 68.36(17) . . ?
C19 Ru1 C20 37.62(15) . . ?
C19 Ru1 C21 67.09(15) . . ?
C20 Ru1 Cl1 87.53(11) . . ?
C20 Ru1 Cl2 138.76(11) . . ?
C20 Ru1 S1 129.49(11) . . ?
C21 Ru1 Cl1 105.80(12) . . ?
C21 Ru1 Cl2 164.88(12) . . ?
C21 Ru1 S1 96.56(11) . . ?
C21 Ru1 C17 69.11(16) . . ?
C21 Ru1 C20 37.00(15) . . ?
C22 Ru1 Cl1 141.63(13) . . ?
C22 Ru1 Cl2 131.04(12) . . ?
C22 Ru1 S1 83.88(11) . . ?
C22 Ru1 C17 38.19(16) . . ?
C22 Ru1 C19 79.84(16) . . ?
C22 Ru1 C20 67.94(15) . . ?
C22 Ru1 C21 38.08(16) . . ?
C1 S1 Ru1 115.60(13) . . ?
C6 O2 C3 106.1(4) . . ?
C15 O4 C16 114.7(4) . . ?
C1 N1 H1 116.9 . . ?
C1 N1 C2 126.3(3) . . ?
C2 N1 H1 116.9 . . ?
C1 N2 H2 117.5 . . ?
C1 N2 C7 125.0(3) . . ?
C7 N2 H2 117.5 . . ?
N1 C1 S1 120.7(3) . . ?
N2 C1 S1 121.1(3) . . ?
N2 C1 N1 118.2(3) . . ?
O1 C2 N1 123.8(4) . . ?
O1 C2 C3 122.8(4) . . ?
N1 C2 C3 113.4(4) . . ?
O2 C3 C2 115.4(4) . . ?
C4 C3 O2 110.7(4) . . ?
C4 C3 C2 133.9(4) . . ?
C3 C4 H4 127.0 . . ?
C3 C4 C5 106.1(5) . . ?
C5 C4 H4 127.0 . . ?
C4 C5 H5 126.7 . . ?
C6 C5 C4 106.5(5) . . ?
C6 C5 H5 126.7 . . ?
O2 C6 H6 124.7 . . ?
C5 C6 O2 110.6(4) . . ?
C5 C6 H6 124.7 . . ?
N2 C7 H7 108.8 . . ?
N2 C7 C8 112.1(3) . . ?
N2 C7 C15 106.8(3) . . ?
C8 C7 H7 108.8 . . ?
C15 C7 H7 108.8 . . ?
C15 C7 C8 111.5(3) . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C9 C8 C7 114.1(3) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 C14 118.5(4) . . ?
C14 C9 C8 120.8(4) . . ?
C9 C10 H10 119.3 . . ?
C9 C10 C11 121.3(4) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(5) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.3(4) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.1(4) . . ?
C13 C14 H14 120.0 . . ?
O3 C15 O4 126.0(4) . . ?
O3 C15 C7 124.3(4) . . ?
O4 C15 C7 109.7(3) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 Ru1 69.2(2) . . ?
C18 C17 C22 115.4(4) . . ?
C18 C17 C23 117.8(4) . . ?
C22 C17 Ru1 69.3(2) . . ?
C22 C17 C23 126.7(5) . . ?
C23 C17 Ru1 129.3(3) . . ?
Ru1 C18 H18 128.2 . . ?
C17 C18 Ru1 73.1(2) . . ?
C17 C18 H18 118.3 . . ?
C19 C18 Ru1 72.7(2) . . ?
C19 C18 C17 123.4(4) . . ?
C19 C18 H18 118.3 . . ?
Ru1 C19 H19 130.5 . . ?
C18 C19 Ru1 69.8(2) . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(4) . . ?
C20 C19 Ru1 72.7(2) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 Ru1 69.7(2) . . ?
C19 C20 C26 120.7(4) . . ?
C21 C20 Ru1 70.1(2) . . ?
C21 C20 C19 117.8(4) . . ?
C21 C20 C26 121.4(4) . . ?
C26 C20 Ru1 129.6(3) . . ?
Ru1 C21 H21 130.3 . . ?
C20 C21 Ru1 72.9(2) . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.6(4) . . ?
C22 C21 Ru1 69.7(2) . . ?
C22 C21 H21 119.7 . . ?
Ru1 C22 H22 128.9 . . ?
C17 C22 Ru1 72.5(2) . . ?
C17 C22 H22 118.9 . . ?
C21 C22 Ru1 72.2(2) . . ?
C21 C22 C17 122.1(4) . . ?
C21 C22 H22 118.9 . . ?
C17 C23 H23 106.5 . . ?
C17 C23 C24 110.0(4) . . ?
C24 C23 H23 106.5 . . ?
C25 C23 C17 112.5(6) . . ?
C25 C23 H23 106.5 . . ?
C25 C23 C24 114.3(5) . . ?
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 . . ?
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 . . ?
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 . . ?

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 2.35 3.195(3) 160.4 .
N2 H2 O1 0.88 1.97 2.655(4) 133.9 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ru1 S1 C1 N1 -21.1(4) . . . . ?
Ru1 S1 C1 N2 158.6(3) . . . . ?
Ru1 C17 C18 C19 55.2(4) . . . . ?
Ru1 C17 C22 C21 -54.8(4) . . . . ?
Ru1 C17 C23 C24 147.7(4) . . . . ?
Ru1 C17 C23 C25 -83.6(6) . . . . ?
Ru1 C18 C19 C20 54.1(4) . . . . ?
Ru1 C19 C20 C21 52.8(3) . . . . ?
Ru1 C19 C20 C26 -124.7(4) . . . . ?
Ru1 C20 C21 C22 52.9(3) . . . . ?
Ru1 C21 C22 C17 54.9(4) . . . . ?
O1 C2 C3 O2 -1.5(6) . . . . ?
O1 C2 C3 C4 179.5(6) . . . . ?
O2 C3 C4 C5 1.7(6) . . . . ?
N1 C2 C3 O2 178.9(4) . . . . ?
N1 C2 C3 C4 -0.1(8) . . . . ?
N2 C7 C8 C9 50.5(5) . . . . ?
N2 C7 C15 O3 -10.3(5) . . . . ?
N2 C7 C15 O4 170.5(3) . . . . ?
C1 N1 C2 O1 8.8(7) . . . . ?
C1 N1 C2 C3 -171.6(4) . . . . ?
C1 N2 C7 C8 82.6(5) . . . . ?
C1 N2 C7 C15 -155.1(4) . . . . ?
C2 N1 C1 S1 168.7(3) . . . . ?
C2 N1 C1 N2 -11.0(6) . . . . ?
C2 C3 C4 C5 -179.3(5) . . . . ?
C3 O2 C6 C5 0.1(6) . . . . ?
C3 C4 C5 C6 -1.6(7) . . . . ?
C4 C5 C6 O2 0.9(8) . . . . ?
C6 O2 C3 C2 179.6(4) . . . . ?
C6 O2 C3 C4 -1.2(6) . . . . ?
C7 N2 C1 S1 -1.9(5) . . . . ?
C7 N2 C1 N1 177.8(4) . . . . ?
C7 C8 C9 C10 -91.9(5) . . . . ?
C7 C8 C9 C14 89.8(4) . . . . ?
C8 C7 C15 O3 112.4(5) . . . . ?
C8 C7 C15 O4 -66.7(4) . . . . ?
C8 C9 C10 C11 -176.6(4) . . . . ?
C8 C9 C14 C13 176.4(4) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C10 C9 C14 C13 -2.0(6) . . . . ?
C10 C11 C12 C13 -0.3(8) . . . . ?
C11 C12 C13 C14 0.1(8) . . . . ?
C12 C13 C14 C9 1.0(7) . . . . ?
C14 C9 C10 C11 1.8(7) . . . . ?
C15 C7 C8 C9 -69.2(5) . . . . ?
C16 O4 C15 O3 1.2(7) . . . . ?
C16 O4 C15 C7 -179.6(5) . . . . ?
C17 C18 C19 Ru1 -55.3(4) . . . . ?
C17 C18 C19 C20 -1.2(6) . . . . ?
C18 C17 C22 Ru1 53.1(3) . . . . ?
C18 C17 C22 C21 -1.6(6) . . . . ?
C18 C17 C23 C24 62.8(6) . . . . ?
C18 C17 C23 C25 -168.6(5) . . . . ?
C18 C19 C20 Ru1 -52.8(4) . . . . ?
C18 C19 C20 C21 0.0(6) . . . . ?
C18 C19 C20 C26 -177.5(4) . . . . ?
C19 C20 C21 Ru1 -52.6(3) . . . . ?
C19 C20 C21 C22 0.3(6) . . . . ?
C20 C21 C22 Ru1 -54.3(3) . . . . ?
C20 C21 C22 C17 0.6(6) . . . . ?
C22 C17 C18 Ru1 -53.2(3) . . . . ?
C22 C17 C18 C19 2.0(6) . . . . ?
C22 C17 C23 C24 -119.9(6) . . . . ?
C22 C17 C23 C25 8.7(7) . . . . ?
C23 C17 C18 Ru1 124.4(4) . . . . ?
C23 C17 C18 C19 179.5(4) . . . . ?
C23 C17 C22 Ru1 -124.2(4) . . . . ?
C23 C17 C22 C21 -179.0(4) . . . . ?
C26 C20 C21 Ru1 124.9(4) . . . . ?
C26 C20 C21 C22 177.8(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_bdpae
_database_code_depnum_ccdc_archive 'CCDC 1474599'
_audit_update_record             
;
2016-04-18 deposited with the CCDC.
2016-07-11 downloaded from the CCDC.
;
_audit_creation_date             2016-04-05
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 N2 O3 S'
_chemical_formula_sum            'C17 H16 N2 O3 S'
_chemical_formula_weight         328.38
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.9242(6)
_cell_length_b                   26.5717(13)
_cell_length_c                   5.0373(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1596.05(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.397
_cell_measurement_theta_min      2.865
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.909
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  0.7436
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1487 before and 0.0837 after correction.
The Ratio of minimum to maximum transmission is 0.8985.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.078
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            33565
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.472
_diffrn_reflns_theta_min         2.295
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3081
_reflns_number_total             3659
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details 
;
 Flack x determined using 1104 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0581
_refine_ls_restrained_S_all      1.104
_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)+(0.0285P)²+2.1251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1138
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C7(H7), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.45767(9) 0.74698(4) -0.2045(2) 0.0211(2) Uani 1 1 d . . . . .
O1 O 0.4279(2) 0.60568(10) 0.2934(6) 0.0203(6) Uani 1 1 d . . . . .
O2 O 0.7836(3) 0.71350(11) -0.3139(6) 0.0268(7) Uani 1 1 d . . . . .
O3 O 0.7212(3) 0.69689(12) 0.0960(6) 0.0271(7) Uani 1 1 d . . . . .
H3 H 0.7812 0.7109 0.1425 0.041 Uiso 1 1 calc GR . . . .
N1 N 0.3829(3) 0.68568(12) 0.1700(7) 0.0178(7) Uani 1 1 d . . . . .
H1 H 0.3392 0.7114 0.2079 0.021 Uiso 1 1 calc R . . . .
N2 N 0.5314(3) 0.65601(12) -0.0786(7) 0.0166(7) Uani 1 1 d . . . . .
H2 H 0.5244 0.6275 0.0089 0.020 Uiso 1 1 calc R . . . .
C1 C 0.3671(3) 0.64261(14) 0.3188(8) 0.0169(8) Uani 1 1 d . . . . .
C2 C 0.2726(3) 0.64279(15) 0.5111(8) 0.0165(9) Uani 1 1 d . . . . .
C3 C 0.2688(4) 0.60383(14) 0.6967(9) 0.0201(9) Uani 1 1 d . . . . .
H3A H 0.3251 0.5785 0.6952 0.024 Uiso 1 1 calc R . . . .
C4 C 0.1844(4) 0.60182(17) 0.8814(8) 0.0237(10) Uani 1 1 d . . . . .
H4 H 0.1823 0.5752 1.0074 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1012(4) 0.63902(17) 0.8842(9) 0.0236(10) Uani 1 1 d . . . . .
H5 H 0.0436 0.6383 1.0146 0.028 Uiso 1 1 calc R . . . .
C6 C 0.1033(4) 0.67648(16) 0.6978(10) 0.0257(10) Uani 1 1 d . . . . .
H6 H 0.0457 0.7012 0.6963 0.031 Uiso 1 1 calc R . . . .
C7 C 0.1882(4) 0.67870(16) 0.5118(8) 0.0225(10) Uani 1 1 d . . . . .
H7 H 0.1888 0.7049 0.3837 0.027 Uiso 1 1 calc R . . . .
C8 C 0.4595(3) 0.69285(14) -0.0311(8) 0.0159(8) Uani 1 1 d . . . . .
C9 C 0.6214(3) 0.66116(14) -0.2708(8) 0.0195(9) Uani 1 1 d . . . . .
H9 H 0.5900 0.6783 -0.4313 0.023 Uiso 1 1 calc R . . . .
C10 C 0.7180(4) 0.69348(15) -0.1664(8) 0.0200(9) Uani 1 1 d . . . . .
C11 C 0.6653(4) 0.60917(16) -0.3578(8) 0.0229(10) Uani 1 1 d . . . . .
H11A H 0.6034 0.5909 -0.4467 0.027 Uiso 1 1 calc R . . . .
H11B H 0.7253 0.6143 -0.4910 0.027 Uiso 1 1 calc R . . . .
C12 C 0.7106(4) 0.57643(15) -0.1397(8) 0.0210(10) Uani 1 1 d . . . . .
C13 C 0.8218(4) 0.58028(17) -0.0597(10) 0.0281(11) Uani 1 1 d . . . . .
H13 H 0.8698 0.6037 -0.1458 0.034 Uiso 1 1 calc R . . . .
C14 C 0.8638(5) 0.55069(18) 0.1425(11) 0.0361(13) Uani 1 1 d . . . . .
H14 H 0.9398 0.5541 0.1957 0.043 Uiso 1 1 calc R . . . .
C15 C 0.7944(4) 0.51587(17) 0.2687(10) 0.0344(12) Uani 1 1 d . . . . .
H15 H 0.8226 0.4956 0.4089 0.041 Uiso 1 1 calc R . . . .
C16 C 0.6858(4) 0.51122(16) 0.1888(10) 0.0328(12) Uani 1 1 d . . . . .
H16 H 0.6384 0.4874 0.2732 0.039 Uiso 1 1 calc R . . . .
C17 C 0.6439(4) 0.54079(16) -0.0134(10) 0.0279(11) Uani 1 1 d . . . . .
H17 H 0.5681 0.5367 -0.0673 0.033 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 1.683(4) . ?
O1 C1 1.227(5) . ?
O2 C10 1.203(5) . ?
O3 H3 0.8400 . ?
O3 C10 1.325(5) . ?
N1 H1 0.8800 . ?
N1 C1 1.381(5) . ?
N1 C8 1.378(5) . ?
N2 H2 0.8800 . ?
N2 C8 1.323(5) . ?
N2 C9 1.452(5) . ?
C1 C2 1.485(6) . ?
C2 C3 1.396(6) . ?
C2 C7 1.387(6) . ?
C3 H3A 0.9500 . ?
C3 C4 1.372(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.401(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.369(6) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(6) . ?
C7 H7 0.9500 . ?
C9 H9 1.0000 . ?
C9 C10 1.530(6) . ?
C9 C11 1.541(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.502(6) . ?
C12 C13 1.390(6) . ?
C12 C17 1.391(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.361(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.380(7) . ?
C17 H17 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
C10 O3 H3 109.5 . . ?
C1 N1 H1 116.4 . . ?
C8 N1 H1 116.4 . . ?
C8 N1 C1 127.2(3) . . ?
C8 N2 H2 119.0 . . ?
C8 N2 C9 122.0(3) . . ?
C9 N2 H2 119.0 . . ?
O1 C1 N1 121.7(4) . . ?
O1 C1 C2 121.3(4) . . ?
N1 C1 C2 117.1(3) . . ?
C3 C2 C1 117.3(4) . . ?
C7 C2 C1 123.6(4) . . ?
C7 C2 C3 119.0(4) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3A 119.8 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.7(4) . . ?
C7 C6 H6 119.7 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.3(4) . . ?
C6 C7 H7 119.9 . . ?
N1 C8 S1 119.4(3) . . ?
N2 C8 S1 123.2(3) . . ?
N2 C8 N1 117.4(3) . . ?
N2 C9 H9 107.7 . . ?
N2 C9 C10 112.3(3) . . ?
N2 C9 C11 110.9(3) . . ?
C10 C9 H9 107.7 . . ?
C10 C9 C11 110.2(3) . . ?
C11 C9 H9 107.7 . . ?
O2 C10 O3 124.5(4) . . ?
O2 C10 C9 121.7(4) . . ?
O3 C10 C9 113.8(4) . . ?
C9 C11 H11A 108.4 . . ?
C9 C11 H11B 108.4 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C9 115.7(3) . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C13 C12 C11 120.8(4) . . ?
C13 C12 C17 117.6(4) . . ?
C17 C12 C11 121.6(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(5) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.9(5) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(5) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.7(5) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.2(5) . . ?
C16 C17 H17 119.4 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 S1 0.84 2.40 3.236(3) 171.2 4_565
N1 H1 O2 0.88 2.17 3.017(4) 161.4 4_465
N2 H2 O1 0.88 1.93 2.612(4) 133.5 .

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 C1 C2 C3 12.2(6) . . . . ?
O1 C1 C2 C7 -166.5(4) . . . . ?
N1 C1 C2 C3 -168.0(4) . . . . ?
N1 C1 C2 C7 13.3(6) . . . . ?
N2 C9 C10 O2 -159.0(4) . . . . ?
N2 C9 C10 O3 21.0(5) . . . . ?
N2 C9 C11 C12 -59.3(5) . . . . ?
C1 N1 C8 S1 175.0(3) . . . . ?
C1 N1 C8 N2 -4.7(6) . . . . ?
C1 C2 C3 C4 179.6(4) . . . . ?
C1 C2 C7 C6 -179.8(4) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C2 C7 C6 1.5(6) . . . . ?
C3 C4 C5 C6 1.6(7) . . . . ?
C4 C5 C6 C7 -1.7(7) . . . . ?
C5 C6 C7 C2 0.2(7) . . . . ?
C7 C2 C3 C4 -1.7(6) . . . . ?
C8 N1 C1 O1 4.5(6) . . . . ?
C8 N1 C1 C2 -175.3(4) . . . . ?
C8 N2 C9 C10 75.9(5) . . . . ?
C8 N2 C9 C11 -160.3(4) . . . . ?
C9 N2 C8 S1 5.5(5) . . . . ?
C9 N2 C8 N1 -174.9(3) . . . . ?
C9 C11 C12 C13 -86.5(5) . . . . ?
C9 C11 C12 C17 94.5(5) . . . . ?
C10 C9 C11 C12 65.8(5) . . . . ?
C11 C9 C10 O2 76.9(5) . . . . ?
C11 C9 C10 O3 -103.2(4) . . . . ?
C11 C12 C13 C14 179.3(4) . . . . ?
C11 C12 C17 C16 -179.3(4) . . . . ?
C12 C13 C14 C15 0.6(7) . . . . ?
C13 C12 C17 C16 1.7(6) . . . . ?
C13 C14 C15 C16 0.5(7) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C12 -0.6(7) . . . . ?
C17 C12 C13 C14 -1.7(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
