# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ad_17
_database_code_depnum_ccdc_archive 'CCDC 1896357'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;

_audit_creation_date             2018-09-22T10:35:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C17 H25 Cl4 N3 Ru S'
_chemical_formula_weight         546.33

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_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'
'-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                   13.077(7)
_cell_length_b                   14.235(6)
_cell_length_c                   23.698(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4412(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6428
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      29.44

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.059
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2208
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 3 0.032
1 2 2 0.025
-1 2 -3 0.077
-1 -1 -2 0.034
-1 2 -2 0.076
-2 0 3 0.051
1 0 -2 0.034
2 -3 1 0.06
-1 -3 5 0.079


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.297
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.8725
_exptl_absorpt_correction_T_max  0.9463

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.1075
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_number            15362
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             4273
_reflns_number_gt                2707
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+93.2979P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4273
_refine_ls_number_parameters     268
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0816
_refine_ls_wR_factor_ref         0.1763
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.945
_refine_diff_density_min         -1.521
_refine_diff_density_rms         0.175

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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'

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 0.70395(6) 0.44441(6) 0.28353(3) 0.0254(2) Uani 1 1 d . . . . .
S1 S 0.8332(2) 0.41239(19) 0.35010(10) 0.0265(6) Uani 1 1 d . . . . .
Cl1 Cl 0.8185(2) 0.5504(2) 0.23553(10) 0.0337(6) Uani 1 1 d . . . . .
Cl3A Cl 0.4061(9) 0.5521(14) 0.4293(8) 0.056(3) Uani 0.59(3) 1 d . . P A 1
N2 N 0.7282(5) 0.5560(6) 0.3921(3) 0.0231(17) Uani 1 1 d . . . . .
N1 N 0.6828(6) 0.5575(6) 0.3393(3) 0.0260(18) Uani 1 1 d . . . . .
C11 C 0.6830(8) 0.2937(7) 0.2734(4) 0.030(2) Uani 1 1 d . . . . .
H11 H 0.7251 0.2453 0.2857 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6997(9) 0.3330(7) 0.2201(4) 0.035(2) Uani 1 1 d . . . . .
H12 H 0.7535 0.3108 0.1981 0.042 Uiso 1 1 calc R U . . .
C1 C 0.8084(8) 0.4924(7) 0.4011(4) 0.026(2) Uani 1 1 d . . . . .
C10 C 0.6031(7) 0.3262(7) 0.3093(4) 0.023(2) Uani 1 1 d . . . . .
C8 C 0.5580(8) 0.4382(9) 0.2333(5) 0.040(3) Uani 1 1 d . . . . .
H8 H 0.5239 0.4973 0.2233 0.048 Uiso 1 1 calc R U . . .
N3 N 0.8639(7) 0.4986(7) 0.4470(4) 0.030(2) Uani 1 1 d D . . . .
H3A H 0.873(8) 0.546(7) 0.469(4) 0.04(3) Uiso 1 1 d D . . . .
H3B H 0.913(9) 0.450(8) 0.454(5) 0.07(4) Uiso 1 1 d D . . . .
C4 C 0.6203(8) 0.6314(7) 0.3379(4) 0.030(2) Uani 1 1 d . . . . .
C2 C 0.6897(8) 0.6305(8) 0.4255(4) 0.030(2) Uani 1 1 d . . . . .
C7 C 0.6369(9) 0.4054(8) 0.1986(4) 0.038(3) Uani 1 1 d . . . . .
C6 C 0.5636(9) 0.6604(8) 0.2875(5) 0.041(3) Uani 1 1 d . . . . .
H6A H 0.5516 0.7269 0.2889 0.062 Uiso 1 1 calc R U . . .
H6B H 0.4994 0.6278 0.2862 0.062 Uiso 1 1 calc R U . . .
H6C H 0.6028 0.6455 0.2545 0.062 Uiso 1 1 calc R U . . .
C13 C 0.5890(8) 0.2838(8) 0.3667(4) 0.029(2) Uani 1 1 d . . . . .
H13 H 0.6569 0.2685 0.3816 0.034 Uiso 1 1 calc R U . . .
C16 C 0.6544(12) 0.4511(11) 0.1416(5) 0.063(4) Uani 1 1 d . . . . .
H16A H 0.6296 0.5145 0.1425 0.094 Uiso 1 1 calc R U . . .
H16B H 0.6185 0.4164 0.1131 0.094 Uiso 1 1 calc R U . . .
H16C H 0.7262 0.4512 0.1332 0.094 Uiso 1 1 calc R U . . .
C5 C 0.7134(9) 0.6456(9) 0.4859(4) 0.042(3) Uani 1 1 d . . . . .
H5A H 0.7062 0.5873 0.506 0.064 Uiso 1 1 calc R U . . .
H5B H 0.6669 0.6911 0.5013 0.064 Uiso 1 1 calc R U . . .
H5C H 0.7822 0.668 0.4897 0.064 Uiso 1 1 calc R U . . .
C9 C 0.5450(8) 0.4025(8) 0.2881(5) 0.033(2) Uani 1 1 d . . . . .
H9 H 0.4963 0.43 0.3115 0.04 Uiso 1 1 calc R U . . .
C3 C 0.6238(7) 0.6764(8) 0.3914(4) 0.030(2) Uani 1 1 d . . . . .
H3 H 0.5863 0.7294 0.4014 0.036 Uiso 1 1 calc R U . . .
C14 C 0.5295(9) 0.1899(8) 0.3589(5) 0.041(3) Uani 1 1 d . . . . .
H14A H 0.46 0.2033 0.3486 0.062 Uiso 1 1 calc R U . . .
H14B H 0.5306 0.1551 0.3935 0.062 Uiso 1 1 calc R U . . .
H14C H 0.5613 0.1535 0.3296 0.062 Uiso 1 1 calc R U . . .
C17 C 0.3477(10) 0.6539(10) 0.4066(6) 0.054(4) Uani 1 1 d . . . . .
H17A H 0.341 0.6548 0.3659 0.065 Uiso 0.59(3) 1 calc R U P A 1
H17B H 0.3857 0.7089 0.4186 0.065 Uiso 0.59(3) 1 calc R U P A 1
H17C H 0.3848 0.7108 0.416 0.065 Uiso 0.41(3) 1 calc R U P A 2
H17D H 0.3639 0.6404 0.3675 0.065 Uiso 0.41(3) 1 calc R U P A 2
C15 C 0.5352(10) 0.3456(10) 0.4098(5) 0.050(3) Uani 1 1 d . . . . .
H15A H 0.573 0.4028 0.4147 0.075 Uiso 1 1 calc R U . . .
H15B H 0.5311 0.313 0.4452 0.075 Uiso 1 1 calc R U . . .
H15C H 0.4675 0.36 0.3968 0.075 Uiso 1 1 calc R U . . .
Cl2 Cl 1.0211(2) 0.34411(19) 0.47720(10) 0.0314(6) Uani 1 1 d . . . . .
Cl4A Cl 0.2198(5) 0.6485(8) 0.4416(7) 0.065(4) Uani 0.59(3) 1 d . . P A 1
Cl3B Cl 0.407(2) 0.564(3) 0.4462(14) 0.101(10) Uani 0.41(3) 1 d . . P A 2
Cl4B Cl 0.2233(7) 0.6844(11) 0.4070(9) 0.054(5) Uani 0.41(3) 1 d . . P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N1 2.101(8) . ?
Ru1 C9 2.166(10) . ?
Ru1 C11 2.175(10) . ?
Ru1 C12 2.187(10) . ?
Ru1 C10 2.223(9) . ?
Ru1 C8 2.251(10) . ?
Ru1 C7 2.264(10) . ?
Ru1 S1 2.357(3) . ?
Ru1 Cl1 2.411(3) . ?
S1 C1 1.693(10) . ?
Cl3A C17 1.72(2) . ?
N2 N1 1.385(10) . ?
N2 C1 1.401(12) . ?
N2 C2 1.416(12) . ?
N1 C4 1.333(13) . ?
C11 C12 1.399(13) . ?
C11 C10 1.424(14) . ?
C12 C7 1.412(15) . ?
C1 N3 1.309(12) . ?
C10 C9 1.417(14) . ?
C10 C13 1.500(13) . ?
C8 C7 1.400(16) . ?
C8 C9 1.405(15) . ?
C4 C3 1.419(14) . ?
C4 C6 1.465(14) . ?
C2 C3 1.351(14) . ?
C2 C5 1.481(13) . ?
C7 C16 1.516(15) . ?
C13 C15 1.521(14) . ?
C13 C14 1.557(14) . ?
C17 Cl4B 1.685(15) . ?
C17 Cl3B 1.77(4) . ?
C17 Cl4A 1.869(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 C9 93.0(4) . . ?
N1 Ru1 C11 143.9(3) . . ?
C9 Ru1 C11 67.2(4) . . ?
N1 Ru1 C12 170.1(4) . . ?
C9 Ru1 C12 79.1(4) . . ?
C11 Ru1 C12 37.4(4) . . ?
N1 Ru1 C10 109.2(3) . . ?
C9 Ru1 C10 37.7(4) . . ?
C11 Ru1 C10 37.8(4) . . ?
C12 Ru1 C10 68.0(4) . . ?
N1 Ru1 C8 104.5(4) . . ?
C9 Ru1 C8 37.0(4) . . ?
C11 Ru1 C8 78.2(4) . . ?
C12 Ru1 C8 65.6(4) . . ?
C10 Ru1 C8 67.2(4) . . ?
N1 Ru1 C7 134.1(4) . . ?
C9 Ru1 C7 66.8(4) . . ?
C11 Ru1 C7 67.1(4) . . ?
C12 Ru1 C7 36.9(4) . . ?
C10 Ru1 C7 80.2(4) . . ?
C8 Ru1 C7 36.1(4) . . ?
N1 Ru1 S1 79.7(2) . . ?
C9 Ru1 S1 127.0(3) . . ?
C11 Ru1 S1 88.5(3) . . ?
C12 Ru1 S1 109.8(3) . . ?
C10 Ru1 S1 95.5(3) . . ?
C8 Ru1 S1 162.6(3) . . ?
C7 Ru1 S1 145.6(3) . . ?
N1 Ru1 Cl1 84.2(2) . . ?
C9 Ru1 Cl1 142.4(3) . . ?
C11 Ru1 Cl1 130.0(3) . . ?
C12 Ru1 Cl1 98.4(3) . . ?
C10 Ru1 Cl1 166.3(3) . . ?
C8 Ru1 Cl1 107.6(3) . . ?
C7 Ru1 Cl1 88.5(3) . . ?
S1 Ru1 Cl1 89.50(10) . . ?
C1 S1 Ru1 102.2(4) . . ?
N1 N2 C1 118.0(7) . . ?
N1 N2 C2 109.9(8) . . ?
C1 N2 C2 131.6(8) . . ?
C4 N1 N2 107.3(8) . . ?
C4 N1 Ru1 132.1(7) . . ?
N2 N1 Ru1 120.0(6) . . ?
C12 C11 C10 121.6(10) . . ?
C12 C11 Ru1 71.7(6) . . ?
C10 C11 Ru1 72.9(6) . . ?
C11 C12 C7 121.8(10) . . ?
C11 C12 Ru1 70.9(5) . . ?
C7 C12 Ru1 74.5(6) . . ?
N3 C1 N2 119.9(9) . . ?
N3 C1 S1 122.1(8) . . ?
N2 C1 S1 117.9(7) . . ?
C9 C10 C11 115.5(9) . . ?
C9 C10 C13 124.3(10) . . ?
C11 C10 C13 120.1(9) . . ?
C9 C10 Ru1 69.0(6) . . ?
C11 C10 Ru1 69.3(5) . . ?
C13 C10 Ru1 128.8(7) . . ?
C7 C8 C9 120.7(10) . . ?
C7 C8 Ru1 72.4(6) . . ?
C9 C8 Ru1 68.2(6) . . ?
N1 C4 C3 108.4(9) . . ?
N1 C4 C6 123.5(10) . . ?
C3 C4 C6 128.1(10) . . ?
C3 C2 N2 104.8(9) . . ?
C3 C2 C5 129.9(10) . . ?
N2 C2 C5 125.1(10) . . ?
C8 C7 C12 117.4(10) . . ?
C8 C7 C16 119.4(12) . . ?
C12 C7 C16 123.1(12) . . ?
C8 C7 Ru1 71.5(6) . . ?
C12 C7 Ru1 68.6(5) . . ?
C16 C7 Ru1 128.9(8) . . ?
C10 C13 C15 115.7(10) . . ?
C10 C13 C14 107.4(8) . . ?
C15 C13 C14 110.2(9) . . ?
C8 C9 C10 122.7(10) . . ?
C8 C9 Ru1 74.8(6) . . ?
C10 C9 Ru1 73.4(6) . . ?
C2 C3 C4 109.6(10) . . ?
Cl4B C17 Cl3B 127.5(15) . . ?
Cl3A C17 Cl4A 102.9(10) . . ?

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
N3 H3A Cl2 0.86(8) 2.45(9) 3.241(9) 153(10) 5_766
N3 H3B Cl2 0.96(8) 2.13(9) 3.096(10) 175(11) .

####################################################################### 
# 
# 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_ad_18
_database_code_depnum_ccdc_archive 'CCDC 1896358'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;

_audit_creation_date             2018-09-22T10:21:13-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H27 Cl2 N3 Ru S'
_chemical_formula_weight         489.45

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
_cell_length_a                   10.6918(18)
_cell_length_b                   14.539(2)
_cell_length_c                   26.597(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4134.5(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    19664
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      29.58

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.033
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -1 -5 0.016
0 -1 -3 0.034
0 -3 4 0.042
-1 3 1 0.065
3 1 5 0.017
1 3 -4 0.052
-1 1 -5 0.024
-5 -2 1 0.024
-1 0 0 0.017
-1 -1 -2 0.024
1 -2 -4 0.047
-1 2 5 0.043
-1 -1 4 0.045
1 -2 -2 0.048


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.9183
_exptl_absorpt_correction_T_max  0.9698

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_number            20018
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.444
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             4043
_reflns_number_gt                3267
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0220P)²+7.3159P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4043
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.061
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_restrained_S_all      1.04
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.08

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
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'

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 0.35550(2) 0.53478(2) 0.32595(2) 0.01332(7) Uani 1 1 d . . . . .
Cl1 Cl 0.24263(7) 0.66602(5) 0.29378(3) 0.02077(15) Uani 1 1 d . . . . .
Cl2 Cl 0.13003(6) 0.55664(5) 0.57147(3) 0.01982(15) Uani 1 1 d . . . . .
S1 S 0.17768(6) 0.49735(5) 0.37199(3) 0.01813(15) Uani 1 1 d . . . . .
N1 N 0.3818(2) 0.62342(15) 0.38760(8) 0.0150(5) Uani 1 1 d . . . . .
N2 N 0.28501(19) 0.63347(15) 0.42266(8) 0.0137(5) Uani 1 1 d . . . . .
N3 N 0.0996(2) 0.57283(17) 0.45577(10) 0.0188(5) Uani 1 1 d . . . . .
H3A H 0.116(3) 0.585(2) 0.4881(14) 0.027(9) Uiso 1 1 d . . . . .
H3B H 0.039(3) 0.539(2) 0.4492(13) 0.028(9) Uiso 1 1 d . . . . .
C4 C 0.4574(2) 0.69445(19) 0.39510(11) 0.0163(6) Uani 1 1 d . . . . .
C3 C 0.4105(3) 0.75138(19) 0.43396(10) 0.0177(6) Uani 1 1 d . . . . .
H3 H 0.4472 0.8052 0.4458 0.021 Uiso 1 1 calc R U . . .
C2 C 0.3024(3) 0.71342(18) 0.45096(10) 0.0155(5) Uani 1 1 d . . . . .
C7 C 0.5730(3) 0.7118(2) 0.36511(12) 0.0227(6) Uani 1 1 d . . . . .
H7A H 0.6046 0.6536 0.3525 0.027 Uiso 1 1 calc R U . . .
H7B H 0.6365 0.738 0.3869 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5506(3) 0.7766(2) 0.32101(12) 0.0306(7) Uani 1 1 d . . . . .
H8A H 0.4868 0.7515 0.2996 0.046 Uiso 1 1 calc R U . . .
H8B H 0.6267 0.7836 0.3022 0.046 Uiso 1 1 calc R U . . .
H8C H 0.5243 0.8355 0.3334 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2158(3) 0.74772(19) 0.49075(11) 0.0189(6) Uani 1 1 d . . . . .
H5A H 0.2199 0.7072 0.5197 0.023 Uiso 1 1 calc R U . . .
H5B H 0.1307 0.7467 0.4781 0.023 Uiso 1 1 calc R U . . .
C6 C 0.2489(3) 0.84557(19) 0.50704(11) 0.0249(7) Uani 1 1 d . . . . .
H6A H 0.2487 0.8853 0.4782 0.037 Uiso 1 1 calc R U . . .
H6B H 0.3305 0.8459 0.5221 0.037 Uiso 1 1 calc R U . . .
H6C H 0.1885 0.867 0.531 0.037 Uiso 1 1 calc R U . . .
C1 C 0.1852(2) 0.57208(19) 0.42036(10) 0.0155(5) Uani 1 1 d . . . . .
C12 C 0.4628(3) 0.40855(19) 0.34132(11) 0.0196(6) Uani 1 1 d . . . . .
C11 C 0.5463(2) 0.48030(18) 0.32636(12) 0.0196(6) Uani 1 1 d . . . . .
H11 H 0.6121 0.4961 0.3475 0.023 Uiso 1 1 calc R U . . .
C10 C 0.5319(3) 0.5282(2) 0.28024(11) 0.0215(6) Uani 1 1 d . . . . .
H10 H 0.5898 0.5729 0.2711 0.026 Uiso 1 1 calc R U . . .
C9 C 0.4297(3) 0.5083(2) 0.24811(12) 0.0231(6) Uani 1 1 d . . . . .
C14 C 0.3443(3) 0.43859(19) 0.26284(11) 0.0213(6) Uani 1 1 d . . . . .
H14 H 0.2758 0.4253 0.2425 0.026 Uiso 1 1 calc R U . . .
C13 C 0.3622(3) 0.38921(18) 0.30799(11) 0.0208(6) Uani 1 1 d . . . . .
H13 H 0.3063 0.3425 0.3162 0.025 Uiso 1 1 calc R U . . .
C19 C 0.4081(3) 0.5627(2) 0.20119(12) 0.0300(7) Uani 1 1 d . . . . .
H19A H 0.3291 0.5938 0.2034 0.045 Uiso 1 1 calc R U . . .
H19B H 0.4075 0.5221 0.1727 0.045 Uiso 1 1 calc R U . . .
H19C H 0.4738 0.6072 0.1973 0.045 Uiso 1 1 calc R U . . .
C15 C 0.4774(3) 0.3556(2) 0.38997(13) 0.0267(7) Uani 1 1 d . . . . .
H15 H 0.3954 0.3301 0.3987 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5210(3) 0.4140(2) 0.43405(13) 0.0313(7) Uani 1 1 d . . . . .
H17A H 0.6038 0.4365 0.4275 0.047 Uiso 1 1 calc R U . . .
H17B H 0.5216 0.3773 0.4641 0.047 Uiso 1 1 calc R U . . .
H17C H 0.465 0.465 0.4384 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5661(4) 0.2750(3) 0.38066(17) 0.0562(12) Uani 1 1 d . . . . .
H16A H 0.5343 0.2377 0.3538 0.084 Uiso 1 1 calc R U . . .
H16B H 0.5726 0.2386 0.4107 0.084 Uiso 1 1 calc R U . . .
H16C H 0.6473 0.2981 0.3717 0.084 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N1 2.104(2) . ?
Ru1 C13 2.171(3) . ?
Ru1 C11 2.188(3) . ?
Ru1 C14 2.188(3) . ?
Ru1 C12 2.203(3) . ?
Ru1 C10 2.246(3) . ?
Ru1 C9 2.250(3) . ?
Ru1 S1 2.3260(7) . ?
Ru1 Cl1 2.4144(7) . ?
S1 C1 1.686(3) . ?
N1 C4 1.326(3) . ?
N1 N2 1.401(3) . ?
N2 C1 1.393(3) . ?
N2 C2 1.397(3) . ?
N3 C1 1.313(4) . ?
N3 H3A 0.90(4) . ?
N3 H3B 0.83(3) . ?
C4 C3 1.416(4) . ?
C4 C7 1.493(4) . ?
C3 C2 1.359(4) . ?
C3 H3 0.93 . ?
C2 C5 1.492(4) . ?
C7 C8 1.523(4) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 H8A 0.96 . ?
C8 H8B 0.96 . ?
C8 H8C 0.96 . ?
C5 C6 1.529(4) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
C12 C13 1.422(4) . ?
C12 C11 1.429(4) . ?
C12 C15 1.514(4) . ?
C11 C10 1.419(4) . ?
C11 H11 0.93 . ?
C10 C9 1.417(4) . ?
C10 H10 0.93 . ?
C9 C14 1.420(4) . ?
C9 C19 1.495(4) . ?
C14 C13 1.412(4) . ?
C14 H14 0.93 . ?
C13 H13 0.93 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C15 C17 1.520(5) . ?
C15 C16 1.528(5) . ?
C15 H15 0.98 . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C16 H16A 0.96 . ?
C16 H16B 0.96 . ?
C16 H16C 0.96 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 C13 139.82(10) . . ?
N1 Ru1 C11 95.34(10) . . ?
C13 Ru1 C11 67.51(10) . . ?
N1 Ru1 C14 175.17(10) . . ?
C13 Ru1 C14 37.80(11) . . ?
C11 Ru1 C14 79.83(11) . . ?
N1 Ru1 C12 107.22(10) . . ?
C13 Ru1 C12 37.95(11) . . ?
C11 Ru1 C12 37.98(10) . . ?
C14 Ru1 C12 68.80(11) . . ?
N1 Ru1 C10 109.61(10) . . ?
C13 Ru1 C10 79.15(11) . . ?
C11 Ru1 C10 37.31(10) . . ?
C14 Ru1 C10 66.63(11) . . ?
C12 Ru1 C10 68.13(10) . . ?
N1 Ru1 C9 140.74(10) . . ?
C13 Ru1 C9 67.63(11) . . ?
C11 Ru1 C9 67.30(11) . . ?
C14 Ru1 C9 37.28(11) . . ?
C12 Ru1 C9 81.07(11) . . ?
C10 Ru1 C9 36.73(11) . . ?
N1 Ru1 S1 80.93(6) . . ?
C13 Ru1 S1 85.10(8) . . ?
C11 Ru1 S1 132.42(8) . . ?
C14 Ru1 S1 102.10(8) . . ?
C12 Ru1 S1 97.65(8) . . ?
C10 Ru1 S1 164.02(8) . . ?
C9 Ru1 S1 137.10(8) . . ?
N1 Ru1 Cl1 81.90(6) . . ?
C13 Ru1 Cl1 135.15(8) . . ?
C11 Ru1 Cl1 138.92(8) . . ?
C14 Ru1 Cl1 101.88(8) . . ?
C12 Ru1 Cl1 169.93(8) . . ?
C10 Ru1 Cl1 105.16(8) . . ?
C9 Ru1 Cl1 89.14(8) . . ?
S1 Ru1 Cl1 87.88(3) . . ?
C1 S1 Ru1 102.24(9) . . ?
C4 N1 N2 105.6(2) . . ?
C4 N1 Ru1 132.48(19) . . ?
N2 N1 Ru1 118.93(16) . . ?
C1 N2 C2 131.2(2) . . ?
C1 N2 N1 118.1(2) . . ?
C2 N2 N1 110.3(2) . . ?
C1 N3 H3A 124(2) . . ?
C1 N3 H3B 113(2) . . ?
H3A N3 H3B 118(3) . . ?
N1 C4 C3 110.4(2) . . ?
N1 C4 C7 123.7(3) . . ?
C3 C4 C7 125.8(2) . . ?
C2 C3 C4 107.9(2) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
C3 C2 N2 105.8(2) . . ?
C3 C2 C5 128.9(2) . . ?
N2 C2 C5 125.3(2) . . ?
C4 C7 C8 112.7(2) . . ?
C4 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C2 C5 C6 111.6(2) . . ?
C2 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C2 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N3 C1 N2 119.8(3) . . ?
N3 C1 S1 121.3(2) . . ?
N2 C1 S1 118.9(2) . . ?
C13 C12 C11 116.3(3) . . ?
C13 C12 C15 120.7(3) . . ?
C11 C12 C15 123.0(3) . . ?
C13 C12 Ru1 69.82(15) . . ?
C11 C12 Ru1 70.45(15) . . ?
C15 C12 Ru1 129.5(2) . . ?
C10 C11 C12 122.1(3) . . ?
C10 C11 Ru1 73.56(16) . . ?
C12 C11 Ru1 71.57(15) . . ?
C10 C11 H11 119 . . ?
C12 C11 H11 119 . . ?
Ru1 C11 H11 128.2 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 Ru1 71.82(16) . . ?
C11 C10 Ru1 69.14(15) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
Ru1 C10 H10 132.2 . . ?
C10 C9 C14 118.3(3) . . ?
C10 C9 C19 121.0(3) . . ?
C14 C9 C19 120.6(3) . . ?
C10 C9 Ru1 71.45(17) . . ?
C14 C9 Ru1 68.98(16) . . ?
C19 C9 Ru1 128.5(2) . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 Ru1 70.44(16) . . ?
C9 C14 Ru1 73.74(17) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
Ru1 C14 H14 128.4 . . ?
C14 C13 C12 122.1(3) . . ?
C14 C13 Ru1 71.76(16) . . ?
C12 C13 Ru1 72.24(16) . . ?
C14 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
Ru1 C13 H13 129.7 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C15 C17 114.0(2) . . ?
C12 C15 C16 108.4(3) . . ?
C17 C15 C16 111.3(3) . . ?
C12 C15 H15 107.7 . . ?
C17 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C1 174.4(2) . . . . ?
Ru1 N1 N2 C1 11.6(3) . . . . ?
C4 N1 N2 C2 1.2(3) . . . . ?
Ru1 N1 N2 C2 -161.65(17) . . . . ?
N2 N1 C4 C3 -0.9(3) . . . . ?
Ru1 N1 C4 C3 158.65(19) . . . . ?
N2 N1 C4 C7 -179.1(2) . . . . ?
Ru1 N1 C4 C7 -19.6(4) . . . . ?
N1 C4 C3 C2 0.2(3) . . . . ?
C7 C4 C3 C2 178.5(3) . . . . ?
C4 C3 C2 N2 0.5(3) . . . . ?
C4 C3 C2 C5 -178.6(3) . . . . ?
C1 N2 C2 C3 -173.1(3) . . . . ?
N1 N2 C2 C3 -1.1(3) . . . . ?
C1 N2 C2 C5 6.0(4) . . . . ?
N1 N2 C2 C5 178.1(2) . . . . ?
N1 C4 C7 C8 94.2(3) . . . . ?
C3 C4 C7 C8 -83.8(4) . . . . ?
C3 C2 C5 C6 9.9(4) . . . . ?
N2 C2 C5 C6 -169.0(3) . . . . ?
C2 N2 C1 N3 -15.8(4) . . . . ?
N1 N2 C1 N3 172.6(2) . . . . ?
C2 N2 C1 S1 164.7(2) . . . . ?
N1 N2 C1 S1 -6.9(3) . . . . ?
Ru1 S1 C1 N3 -179.8(2) . . . . ?
Ru1 S1 C1 N2 -0.3(2) . . . . ?
C13 C12 C11 C10 -1.6(4) . . . . ?
C15 C12 C11 C10 179.1(3) . . . . ?
Ru1 C12 C11 C10 -55.9(2) . . . . ?
C13 C12 C11 Ru1 54.3(2) . . . . ?
C15 C12 C11 Ru1 -125.0(3) . . . . ?
C12 C11 C10 C9 2.6(4) . . . . ?
Ru1 C11 C10 C9 -52.4(2) . . . . ?
C12 C11 C10 Ru1 55.0(2) . . . . ?
C11 C10 C9 C14 -1.1(4) . . . . ?
Ru1 C10 C9 C14 -52.3(2) . . . . ?
C11 C10 C9 C19 175.6(3) . . . . ?
Ru1 C10 C9 C19 124.4(3) . . . . ?
C11 C10 C9 Ru1 51.2(2) . . . . ?
C10 C9 C14 C13 -1.1(4) . . . . ?
C19 C9 C14 C13 -177.9(3) . . . . ?
Ru1 C9 C14 C13 -54.6(2) . . . . ?
C10 C9 C14 Ru1 53.5(2) . . . . ?
C19 C9 C14 Ru1 -123.2(3) . . . . ?
C9 C14 C13 C12 2.1(4) . . . . ?
Ru1 C14 C13 C12 -54.1(2) . . . . ?
C9 C14 C13 Ru1 56.2(2) . . . . ?
C11 C12 C13 C14 -0.7(4) . . . . ?
C15 C12 C13 C14 178.6(3) . . . . ?
Ru1 C12 C13 C14 53.9(2) . . . . ?
C11 C12 C13 Ru1 -54.6(2) . . . . ?
C15 C12 C13 Ru1 124.7(3) . . . . ?
C13 C12 C15 C17 -141.6(3) . . . . ?
C11 C12 C15 C17 37.7(4) . . . . ?
Ru1 C12 C15 C17 -53.3(4) . . . . ?
C13 C12 C15 C16 94.0(3) . . . . ?
C11 C12 C15 C16 -86.8(4) . . . . ?
Ru1 C12 C15 C16 -177.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A Cl2 0.90(4) 2.26(4) 3.103(3) 157(3) .
N3 H3B Cl2 0.83(3) 2.35(4) 3.177(3) 178(3) 5_566

####################################################################### 
# 
# 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_ad2_2019
_database_code_depnum_ccdc_archive 'CCDC 1896360'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;

_audit_creation_date             2019-02-05T15:13:58-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C15 H22 Cl N3 O2 Ru S'
_chemical_formula_weight         444.93
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.398(2)
_cell_length_b                   12.551(3)
_cell_length_c                   13.766(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1796.6(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7937
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      29.53

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.044
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 2 -4 0.014
-1 -2 3 0.03
-1 5 3 0.044
1 -6 -3 0.051
3 -4 0 0.052
-3 -2 -2 0.046
-4 1 -1 0.044
4 1 2 0.048


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.149
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.9227
_exptl_absorpt_correction_T_max  0.9606

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_number            10472
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.943
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     1
_reflns_Friedel_coverage         0.752
_reflns_number_total             3509
_reflns_number_gt                2872
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+4.2001P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3509
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.0906
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.113

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.61142(6) 0.50850(5) 0.34115(5) 0.01840(16) Uani 1 1 d . . . . .
Cl1 Cl 0.6660(2) 0.37389(16) 0.22129(16) 0.0247(5) Uani 1 1 d . . . . .
S1 S 0.5461(2) 0.37239(18) 0.44964(18) 0.0243(5) Uani 1 1 d . . . . .
N1 N 0.4246(6) 0.4848(6) 0.2901(5) 0.0242(15) Uani 1 1 d . . . . .
C6 C 0.7862(9) 0.6004(7) 0.2951(7) 0.026(2) Uani 1 1 d . . . . .
N2 N 0.3422(6) 0.4185(5) 0.3437(6) 0.0243(15) Uani 1 1 d . . . . .
C11 C 0.6761(9) 0.6623(6) 0.2766(7) 0.027(2) Uani 1 1 d . . . . .
H11 H 0.6638 0.6919 0.2154 0.033 Uiso 1 1 calc R U . . .
O2 O 0.8861(7) 0.2861(5) 0.3610(5) 0.0418(17) Uani 1 1 d G . . . .
H2A H 0.9604 0.3102 0.3473 0.063 Uiso 1 1 d G U . . .
H2B H 0.8301 0.3173 0.3262 0.063 Uiso 1 1 d G U . . .
C10 C 0.5831(8) 0.6801(5) 0.3512(7) 0.028(2) Uani 1 1 d . . . . .
H10 H 0.5097 0.7195 0.3369 0.033 Uiso 1 1 calc R U . . .
N3 N 0.3081(7) 0.2970(6) 0.4658(6) 0.0309(18) Uani 1 1 d . . . . .
H3A H 0.229 0.2926 0.4478 0.037 Uiso 1 1 calc R U . . .
H3B H 0.3351 0.2597 0.514 0.037 Uiso 1 1 calc R U . . .
C12 C 0.8810(11) 0.5764(7) 0.2160(7) 0.039(2) Uani 1 1 d . . . . .
H12A H 0.903 0.5022 0.2177 0.059 Uiso 1 1 calc R U . . .
H12B H 0.9572 0.6184 0.2255 0.059 Uiso 1 1 calc R U . . .
H12C H 0.8436 0.5934 0.1541 0.059 Uiso 1 1 calc R U . . .
C1 C 0.3879(9) 0.3610(6) 0.4193(6) 0.0228(17) Uani 1 1 d . . . . .
C7 C 0.8053(9) 0.5582(7) 0.3900(7) 0.025(2) Uani 1 1 d . . . . .
H7 H 0.8778 0.5176 0.4038 0.03 Uiso 1 1 calc R U . . .
C5 C 0.4111(10) 0.5907(8) 0.1411(7) 0.040(3) Uani 1 1 d . . . . .
H5A H 0.4 0.6637 0.1602 0.059 Uiso 1 1 calc R U . . .
H5B H 0.3684 0.5788 0.0802 0.059 Uiso 1 1 calc R U . . .
H5C H 0.5011 0.5756 0.1342 0.059 Uiso 1 1 calc R U . . .
O1 O 0.1295(6) 0.3606(6) 0.3368(6) 0.0504(19) Uani 1 1 d . . . . .
C3 C 0.2285(9) 0.4815(8) 0.2203(7) 0.035(2) Uani 1 1 d . . . . .
H3 H 0.1632 0.4975 0.1764 0.042 Uiso 1 1 calc R U . . .
C9 C 0.5997(9) 0.6393(6) 0.4467(6) 0.0228(18) Uani 1 1 d . . . . .
C13 C 0.5042(9) 0.6550(7) 0.5280(7) 0.029(2) Uani 1 1 d . . . . .
H13 H 0.5067 0.5911 0.5689 0.035 Uiso 1 1 calc R U . . .
C15 C 0.3673(10) 0.6684(7) 0.4924(8) 0.039(3) Uani 1 1 d . . . . .
H15A H 0.3612 0.7318 0.4536 0.059 Uiso 1 1 calc R U . . .
H15B H 0.3104 0.6741 0.547 0.059 Uiso 1 1 calc R U . . .
H15C H 0.3434 0.6078 0.4538 0.059 Uiso 1 1 calc R U . . .
C8 C 0.7132(8) 0.5785(6) 0.4624(7) 0.0217(19) Uani 1 1 d . . . . .
H8 H 0.7274 0.5507 0.5241 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3551(8) 0.5200(7) 0.2160(7) 0.029(2) Uani 1 1 d . . . . .
C2 C 0.2169(9) 0.4164(7) 0.3001(8) 0.033(2) Uani 1 1 d . . . . .
C14 C 0.5452(10) 0.7492(9) 0.5908(8) 0.044(3) Uani 1 1 d . . . . .
H14A H 0.6313 0.7379 0.6138 0.067 Uiso 1 1 calc R U . . .
H14B H 0.4879 0.7557 0.6452 0.067 Uiso 1 1 calc R U . . .
H14C H 0.5423 0.8134 0.5529 0.067 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N1 2.087(6) . ?
Ru1 C8 2.164(9) . ?
Ru1 C10 2.179(7) . ?
Ru1 C9 2.195(8) . ?
Ru1 C7 2.214(9) . ?
Ru1 C11 2.229(8) . ?
Ru1 C6 2.244(9) . ?
Ru1 S1 2.369(2) . ?
Ru1 Cl1 2.429(2) . ?
S1 C1 1.703(10) . ?
N1 C4 1.326(10) . ?
N1 N2 1.404(9) . ?
C6 C11 1.407(13) . ?
C6 C7 1.423(13) . ?
C6 C12 1.500(12) . ?
N2 C1 1.353(11) . ?
N2 C2 1.434(11) . ?
C11 C10 1.428(12) . ?
C10 C9 1.422(12) . ?
N3 C1 1.320(11) . ?
C7 C8 1.406(12) . ?
C5 C4 1.481(12) . ?
O1 C2 1.254(11) . ?
C3 C2 1.375(14) . ?
C3 C4 1.403(12) . ?
C9 C8 1.421(12) . ?
C9 C13 1.510(12) . ?
C13 C15 1.516(13) . ?
C13 C14 1.526(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 C8 140.6(3) . . ?
N1 Ru1 C10 92.1(3) . . ?
C8 Ru1 C10 67.4(3) . . ?
N1 Ru1 C9 106.1(3) . . ?
C8 Ru1 C9 38.0(3) . . ?
C10 Ru1 C9 37.9(3) . . ?
N1 Ru1 C7 171.7(3) . . ?
C8 Ru1 C7 37.5(3) . . ?
C10 Ru1 C7 80.0(3) . . ?
C9 Ru1 C7 68.8(3) . . ?
N1 Ru1 C11 105.7(3) . . ?
C8 Ru1 C11 78.9(3) . . ?
C10 Ru1 C11 37.8(3) . . ?
C9 Ru1 C11 68.5(3) . . ?
C7 Ru1 C11 66.6(3) . . ?
N1 Ru1 C6 137.1(3) . . ?
C8 Ru1 C6 67.2(4) . . ?
C10 Ru1 C6 67.6(3) . . ?
C9 Ru1 C6 81.2(3) . . ?
C7 Ru1 C6 37.2(3) . . ?
C11 Ru1 C6 36.7(3) . . ?
N1 Ru1 S1 80.9(2) . . ?
C8 Ru1 S1 86.9(2) . . ?
C10 Ru1 S1 129.4(3) . . ?
C9 Ru1 S1 96.1(2) . . ?
C7 Ru1 S1 105.8(3) . . ?
C11 Ru1 S1 164.3(2) . . ?
C6 Ru1 S1 141.4(3) . . ?
N1 Ru1 Cl1 83.7(2) . . ?
C8 Ru1 Cl1 133.8(2) . . ?
C10 Ru1 Cl1 139.7(3) . . ?
C9 Ru1 Cl1 169.3(3) . . ?
C7 Ru1 Cl1 100.9(2) . . ?
C11 Ru1 Cl1 105.1(2) . . ?
C6 Ru1 Cl1 88.7(2) . . ?
S1 Ru1 Cl1 89.64(8) . . ?
C1 S1 Ru1 100.5(3) . . ?
C4 N1 N2 105.6(6) . . ?
C4 N1 Ru1 136.0(6) . . ?
N2 N1 Ru1 118.4(5) . . ?
C11 C6 C7 119.0(9) . . ?
C11 C6 C12 120.9(9) . . ?
C7 C6 C12 120.0(9) . . ?
C11 C6 Ru1 71.1(5) . . ?
C7 C6 Ru1 70.3(5) . . ?
C12 C6 Ru1 129.4(6) . . ?
C1 N2 N1 120.4(6) . . ?
C1 N2 C2 129.1(8) . . ?
N1 N2 C2 110.2(7) . . ?
C6 C11 C10 120.5(8) . . ?
C6 C11 Ru1 72.2(5) . . ?
C10 C11 Ru1 69.2(4) . . ?
C9 C10 C11 121.7(8) . . ?
C9 C10 Ru1 71.7(4) . . ?
C11 C10 Ru1 73.0(4) . . ?
N3 C1 N2 118.5(8) . . ?
N3 C1 S1 122.6(7) . . ?
N2 C1 S1 118.9(6) . . ?
C8 C7 C6 119.2(9) . . ?
C8 C7 Ru1 69.3(5) . . ?
C6 C7 Ru1 72.5(5) . . ?
C2 C3 C4 108.7(8) . . ?
C8 C9 C10 115.8(8) . . ?
C8 C9 C13 120.2(8) . . ?
C10 C9 C13 123.9(8) . . ?
C8 C9 Ru1 69.8(5) . . ?
C10 C9 Ru1 70.4(4) . . ?
C13 C9 Ru1 128.7(6) . . ?
C9 C13 C15 113.1(8) . . ?
C9 C13 C14 109.7(8) . . ?
C15 C13 C14 111.1(7) . . ?
C7 C8 C9 123.7(8) . . ?
C7 C8 Ru1 73.2(5) . . ?
C9 C8 Ru1 72.2(5) . . ?
N1 C4 C3 111.4(8) . . ?
N1 C4 C5 121.4(7) . . ?
C3 C4 C5 127.2(8) . . ?
O1 C2 C3 135.9(10) . . ?
O1 C2 N2 120.0(9) . . ?
C3 C2 N2 104.1(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
O2 H2A O1 0.85 1.87 2.718(9) 171.4 1_655
O2 H2B Cl1 0.85 2.35 3.186(7) 170.1 .
N3 H3A O1 0.86 2.03 2.690(11) 132.5 .
N3 H3B O2 0.86 1.89 2.726(11) 163.9 4_456

####################################################################### 
# 
# 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_ad1_2019
_database_code_depnum_ccdc_archive 'CCDC 1896359'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2019-02-09 deposited with the CCDC.	2019-11-19 downloaded from the CCDC.
;

_audit_creation_date             2019-01-13T12:08:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H22 Cl N3 O Ru S'
_chemical_formula_weight         488.98

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6196(18)
_cell_length_b                   12.7321(17)
_cell_length_c                   14.8584(15)
_cell_angle_alpha                90
_cell_angle_beta                 107.980(11)
_cell_angle_gamma                90
_cell_volume                     1910.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5958
_cell_measurement_theta_min      3.82
_cell_measurement_theta_max      29.55

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.059
_exptl_crystal_size_min          0.029
_exptl_crystal_density_diffrn    1.7
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             992
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -2 -2 0.006
-3 2 1 0.023
1 2 -5 0.034
0 -3 5 0.039
-2 -3 3 0.041
-1 -2 -2 0.037
1 1 -2 0.037
1 3 2 0.038
-1 0 5 0.047


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.9307
_exptl_absorpt_correction_T_max  0.9739

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0592
_diffrn_reflns_number            9994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.2
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_reflns_Friedel_coverage         0
_reflns_number_total             3737
_reflns_number_gt                2790
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+5.8878P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3737
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.04
_refine_ls_wR_factor_ref         0.086
_refine_ls_wR_factor_gt          0.0776
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.73
_refine_diff_density_rms         0.118

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.69589(4) 0.59139(3) 0.34554(2) 0.01281(10) Uani 1 1 d . . . . .
Cl1 Cl 0.80576(11) 0.55478(8) 0.51257(7) 0.0175(2) Uani 1 1 d . . . . .
C13 C 0.6597(5) 0.4787(3) 0.2312(3) 0.0173(9) Uani 1 1 d . . . . .
H13 H 0.5974 0.4251 0.2146 0.021 Uiso 1 1 calc R U . . .
S1 S 0.49721(11) 0.53240(8) 0.36884(8) 0.0178(2) Uani 1 1 d . . . . .
C1 C 0.4475(4) 0.6427(3) 0.4112(3) 0.0165(9) Uani 1 1 d . . . . .
N3 N 0.3401(4) 0.6486(3) 0.4369(3) 0.0210(9) Uani 1 1 d . . . . .
H3A H 0.3188 0.707 0.4575 0.025 Uiso 1 1 calc R U . . .
H3B H 0.2909 0.5941 0.4332 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6251(4) 0.5790(3) 0.1906(3) 0.0170(9) Uani 1 1 d . . . . .
H12 H 0.5411 0.5905 0.1484 0.02 Uiso 1 1 calc R U . . .
C11 C 0.7179(5) 0.6620(3) 0.2140(3) 0.0176(10) Uani 1 1 d . . . . .
C16 C 0.8460(4) 0.6414(3) 0.2778(3) 0.0171(9) Uani 1 1 d . . . . .
H16 H 0.9093 0.6944 0.2927 0.021 Uiso 1 1 calc R U . . .
C15 C 0.8776(5) 0.5413(4) 0.3186(3) 0.0198(10) Uani 1 1 d . . . . .
H15 H 0.9611 0.5298 0.3615 0.024 Uiso 1 1 calc R U . . .
C14 C 0.7848(5) 0.4569(3) 0.2957(3) 0.0184(10) Uani 1 1 d . . . . .
C17 C 0.6818(5) 0.7697(3) 0.1727(3) 0.0230(10) Uani 1 1 d . . . . .
H17A H 0.5876 0.7789 0.1556 0.034 Uiso 1 1 calc R U . . .
H17B H 0.7098 0.7773 0.1176 0.034 Uiso 1 1 calc R U . . .
H17C H 0.7248 0.8217 0.2187 0.034 Uiso 1 1 calc R U . . .
C18 C 0.8230(5) 0.3508(3) 0.3415(3) 0.0229(11) Uani 1 1 d . . . . .
H18 H 0.8685 0.3626 0.4089 0.028 Uiso 1 1 calc R U . . .
C19 C 0.7026(5) 0.2797(4) 0.3338(4) 0.0287(12) Uani 1 1 d . . . . .
H19A H 0.6426 0.3153 0.3603 0.043 Uiso 1 1 calc R U . . .
H19B H 0.7319 0.2156 0.3678 0.043 Uiso 1 1 calc R U . . .
H19C H 0.6583 0.2641 0.2684 0.043 Uiso 1 1 calc R U . . .
C20 C 0.9202(6) 0.2974(4) 0.3001(4) 0.0316(12) Uani 1 1 d . . . . .
H20A H 0.8768 0.2809 0.2348 0.047 Uiso 1 1 calc R U . . .
H20B H 0.952 0.2339 0.3345 0.047 Uiso 1 1 calc R U . . .
H20C H 0.9934 0.3436 0.3048 0.047 Uiso 1 1 calc R U . . .
N2 N 0.5205(4) 0.7327(3) 0.4191(2) 0.0152(8) Uani 1 1 d . . . . .
N1 N 0.6392(4) 0.7332(3) 0.3954(3) 0.0150(8) Uani 1 1 d . . . . .
C5 C 0.8174(4) 0.8630(3) 0.4109(3) 0.0165(9) Uani 1 1 d . . . . .
C4 C 0.6882(4) 0.8305(3) 0.4186(3) 0.0128(9) Uani 1 1 d . . . . .
C2 C 0.4962(4) 0.8325(3) 0.4559(3) 0.0139(9) Uani 1 1 d . . . . .
C6 C 0.9329(5) 0.8061(4) 0.4539(3) 0.0220(10) Uani 1 1 d . . . . .
H6 H 0.9284 0.7447 0.4867 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6064(4) 0.8928(3) 0.4541(3) 0.0163(9) Uani 1 1 d . . . . .
H3 H 0.6221 0.9623 0.4734 0.02 Uiso 1 1 calc R U . . .
C10 C 0.8264(5) 0.9567(4) 0.3637(4) 0.0242(11) Uani 1 1 d . . . . .
H10 H 0.7508 0.9967 0.337 0.029 Uiso 1 1 calc R U . . .
C9 C 0.9466(6) 0.9900(4) 0.3566(4) 0.0311(13) Uani 1 1 d . . . . .
H9 H 0.951 1.0498 0.3217 0.037 Uiso 1 1 calc R U . . .
C8 C 1.0611(5) 0.9343(4) 0.4016(4) 0.0313(13) Uani 1 1 d . . . . .
H8 H 1.1431 0.9591 0.4008 0.038 Uiso 1 1 calc R U . . .
C7 C 1.0521(5) 0.8398(4) 0.4484(3) 0.0259(11) Uani 1 1 d . . . . .
H7 H 1.1279 0.8002 0.4757 0.031 Uiso 1 1 calc R U . . .
O1 O 0.3955(3) 0.8481(2) 0.4807(2) 0.0221(7) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 N1 2.109(4) . ?
Ru1 C13 2.165(4) . ?
Ru1 C15 2.184(5) . ?
Ru1 C14 2.191(4) . ?
Ru1 C12 2.196(4) . ?
Ru1 C16 2.224(4) . ?
Ru1 C11 2.228(4) . ?
Ru1 S1 2.3635(12) . ?
Ru1 Cl1 2.4393(11) . ?
C13 C14 1.405(6) . ?
C13 C12 1.412(6) . ?
C13 H13 0.93 . ?
S1 C1 1.688(4) . ?
C1 N3 1.312(6) . ?
C1 N2 1.368(5) . ?
N3 H3A 0.86 . ?
N3 H3B 0.86 . ?
C12 C11 1.413(6) . ?
C12 H12 0.93 . ?
C11 C16 1.422(6) . ?
C11 C17 1.503(6) . ?
C16 C15 1.407(6) . ?
C16 H16 0.93 . ?
C15 C14 1.425(6) . ?
C15 H15 0.93 . ?
C14 C18 1.511(6) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C18 C20 1.516(7) . ?
C18 C19 1.542(7) . ?
C18 H18 0.98 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
N2 N1 1.410(5) . ?
N2 C2 1.438(5) . ?
N1 C4 1.346(5) . ?
C5 C6 1.399(6) . ?
C5 C10 1.402(6) . ?
C5 C4 1.471(6) . ?
C4 C3 1.395(6) . ?
C2 O1 1.250(5) . ?
C2 C3 1.406(6) . ?
C6 C7 1.363(7) . ?
C6 H6 0.93 . ?
C3 H3 0.93 . ?
C10 C9 1.380(7) . ?
C10 H10 0.93 . ?
C9 C8 1.388(8) . ?
C9 H9 0.93 . ?
C8 C7 1.407(7) . ?
C8 H8 0.93 . ?
C7 H7 0.93 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 C13 147.36(16) . . ?
N1 Ru1 C15 132.76(16) . . ?
C13 Ru1 C15 67.37(17) . . ?
N1 Ru1 C14 170.78(16) . . ?
C13 Ru1 C14 37.63(16) . . ?
C15 Ru1 C14 38.03(17) . . ?
N1 Ru1 C12 112.77(15) . . ?
C13 Ru1 C12 37.77(16) . . ?
C15 Ru1 C12 79.79(17) . . ?
C14 Ru1 C12 68.51(16) . . ?
N1 Ru1 C16 103.64(15) . . ?
C13 Ru1 C16 79.22(17) . . ?
C15 Ru1 C16 37.21(16) . . ?
C14 Ru1 C16 68.10(17) . . ?
C12 Ru1 C16 66.89(16) . . ?
N1 Ru1 C11 94.65(15) . . ?
C13 Ru1 C11 67.68(16) . . ?
C15 Ru1 C11 67.63(17) . . ?
C14 Ru1 C11 81.15(16) . . ?
C12 Ru1 C11 37.23(16) . . ?
C16 Ru1 C11 37.26(16) . . ?
N1 Ru1 S1 81.72(10) . . ?
C13 Ru1 S1 87.39(12) . . ?
C15 Ru1 S1 144.42(12) . . ?
C14 Ru1 S1 107.38(13) . . ?
C12 Ru1 S1 95.67(12) . . ?
C16 Ru1 S1 162.53(12) . . ?
C11 Ru1 S1 126.63(13) . . ?
N1 Ru1 Cl1 84.55(10) . . ?
C13 Ru1 Cl1 125.81(12) . . ?
C15 Ru1 Cl1 87.62(12) . . ?
C14 Ru1 Cl1 94.23(12) . . ?
C12 Ru1 Cl1 162.64(12) . . ?
C16 Ru1 Cl1 109.29(12) . . ?
C11 Ru1 Cl1 145.37(12) . . ?
S1 Ru1 Cl1 87.62(4) . . ?
C14 C13 C12 122.5(4) . . ?
C14 C13 Ru1 72.2(2) . . ?
C12 C13 Ru1 72.3(2) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
Ru1 C13 H13 129.3 . . ?
C1 S1 Ru1 100.74(16) . . ?
N3 C1 N2 116.6(4) . . ?
N3 C1 S1 123.8(3) . . ?
N2 C1 S1 119.6(3) . . ?
C1 N3 H3A 120 . . ?
C1 N3 H3B 120 . . ?
H3A N3 H3B 120 . . ?
C13 C12 C11 120.1(4) . . ?
C13 C12 Ru1 69.9(2) . . ?
C11 C12 Ru1 72.6(2) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
Ru1 C12 H12 130 . . ?
C12 C11 C16 118.5(4) . . ?
C12 C11 C17 120.7(4) . . ?
C16 C11 C17 120.8(4) . . ?
C12 C11 Ru1 70.1(2) . . ?
C16 C11 Ru1 71.2(2) . . ?
C17 C11 Ru1 130.1(3) . . ?
C15 C16 C11 120.4(4) . . ?
C15 C16 Ru1 69.8(3) . . ?
C11 C16 Ru1 71.5(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
Ru1 C16 H16 131.8 . . ?
C16 C15 C14 121.6(4) . . ?
C16 C15 Ru1 73.0(3) . . ?
C14 C15 Ru1 71.3(3) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
Ru1 C15 H15 129 . . ?
C13 C14 C15 116.9(4) . . ?
C13 C14 C18 123.3(4) . . ?
C15 C14 C18 119.8(4) . . ?
C13 C14 Ru1 70.2(2) . . ?
C15 C14 Ru1 70.7(2) . . ?
C18 C14 Ru1 129.1(3) . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 C20 109.9(4) . . ?
C14 C18 C19 113.0(4) . . ?
C20 C18 C19 111.1(4) . . ?
C14 C18 H18 107.6 . . ?
C20 C18 H18 107.6 . . ?
C19 C18 H18 107.6 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N2 N1 120.6(3) . . ?
C1 N2 C2 127.6(4) . . ?
N1 N2 C2 111.7(3) . . ?
C4 N1 N2 104.2(3) . . ?
C4 N1 Ru1 138.4(3) . . ?
N2 N1 Ru1 117.2(3) . . ?
C6 C5 C10 119.0(4) . . ?
C6 C5 C4 121.7(4) . . ?
C10 C5 C4 119.2(4) . . ?
N1 C4 C3 112.5(4) . . ?
N1 C4 C5 122.4(4) . . ?
C3 C4 C5 125.1(4) . . ?
O1 C2 C3 135.4(4) . . ?
O1 C2 N2 121.5(4) . . ?
C3 C2 N2 103.2(4) . . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C4 C3 C2 108.4(4) . . ?
C4 C3 H3 125.8 . . ?
C2 C3 H3 125.8 . . ?
C9 C10 C5 120.5(5) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C10 C9 C8 120.0(5) . . ?
C10 C9 H9 120 . . ?
C8 C9 H9 120 . . ?
C9 C8 C7 119.5(5) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C6 C7 C8 120.3(5) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?

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
N3 H3A O1 0.86 1.96 2.643(5) 135.7 .
N3 H3B Cl1 0.86 2.41 3.222(4) 157.9 3_666
C3 H3 O1 0.93 2.53 3.440(5) 166 3_676

