# Electronic Supplementary Material (ESI) for ChemComm.
# 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_A1Py_2_0msp_a
_database_code_depnum_ccdc_archive 'CCDC 1879831'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H27 F3 N2 O4 Ru S'
_chemical_formula_weight         645.64

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.1052(16)
_cell_length_b                   16.953(2)
_cell_length_c                   12.9887(17)
_cell_angle_alpha                90
_cell_angle_beta                 92.587(5)
_cell_angle_gamma                90
_cell_volume                     2662.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9728
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      30.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.011
_exptl_absorpt_coefficient_mu    0.726
_shelx_estimated_absorpt_T_min   0.839
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7132
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   Sadabs-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'high brilliance microfocus sealed tube '
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            292047
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.976
_diffrn_reflns_theta_max         30.626
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8194
_reflns_number_gt                7634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'APEX3 2017.3 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;

The triflate anion is disordered over two positions, ca. 51:49.

The CHO ligandi is disordered over two posiotion, ca. 52%:48%.
The CH3 ligand is also disordered over two positions, ca. 70%:30%.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0127P)²+3.2840P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8194
_refine_ls_number_parameters     458
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0617
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.30776(2) 0.34968(2) 0.67847(2) 0.01427(3) Uani 1 1 d . . . . .
N1 N 0.28897(11) 0.39165(8) 0.52803(10) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.12933(13) 0.35251(10) 0.70102(16) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.15449(15) 0.27303(11) 0.6712(2) 0.0393(5) Uani 1 1 d . . . . .
H2 H 0.113890 0.249434 0.615009 0.047 Uiso 1 1 calc R U . . .
C3 C 0.23734(17) 0.23027(12) 0.7235(2) 0.0447(6) Uani 1 1 d . . . . .
H3 H 0.252656 0.177834 0.702627 0.054 Uiso 1 1 calc R U . . .
C4 C 0.29944(18) 0.26415(14) 0.8079(2) 0.0430(6) Uani 1 1 d D . . . .
C5 C 0.27164(17) 0.33994(14) 0.84192(16) 0.0371(5) Uani 1 1 d . . . . .
H5 H 0.309272 0.361888 0.900958 0.045 Uiso 1 1 calc R U . . .
C6 C 0.18628(15) 0.38436(11) 0.78752(14) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.168371 0.435796 0.810516 0.033 Uiso 1 1 calc R U . . .
C7 C 0.04265(14) 0.39779(11) 0.63679(16) 0.0284(4) Uani 1 1 d . . . . .
H7 H 0.055560 0.386660 0.562689 0.034 Uiso 1 1 calc R U . . .
C8 C -0.07196(16) 0.36623(14) 0.6591(2) 0.0425(6) Uani 1 1 d . . . . .
H8A H -0.088187 0.377731 0.730782 0.064 Uiso 1 1 calc R U . . .
H8B H -0.073824 0.309073 0.647892 0.064 Uiso 1 1 calc R U . . .
H8C H -0.127439 0.391646 0.612876 0.064 Uiso 1 1 calc R U . . .
C9 C 0.04968(17) 0.48686(12) 0.65174(18) 0.0340(4) Uani 1 1 d . . . . .
H9A H 0.031037 0.500170 0.722303 0.051 Uiso 1 1 calc R U . . .
H9B H -0.002467 0.512914 0.602864 0.051 Uiso 1 1 calc R U . . .
H9C H 0.124975 0.504762 0.639676 0.051 Uiso 1 1 calc R U . . .
C10 C 0.3967(7) 0.2250(8) 0.8703(10) 0.046(2) Uani 0.71(3) 1 d D . P A 1
H10A H 0.439667 0.265581 0.907935 0.070 Uiso 0.71(3) 1 calc R U P A 1
H10B H 0.444391 0.197292 0.823181 0.070 Uiso 0.71(3) 1 calc R U P A 1
H10C H 0.367557 0.187210 0.919399 0.070 Uiso 0.71(3) 1 calc R U P A 1
C10B C 0.3811(11) 0.2035(8) 0.8429(12) 0.026(2) Uani 0.29(3) 1 d D . P A 2
H10D H 0.439599 0.228338 0.886235 0.039 Uiso 0.29(3) 1 calc R U P A 2
H10E H 0.413457 0.179172 0.782811 0.039 Uiso 0.29(3) 1 calc R U P A 2
H10F H 0.344055 0.163022 0.882659 0.039 Uiso 0.29(3) 1 calc R U P A 2
C11 C 0.38168(12) 0.45808(9) 0.69052(12) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.43401(14) 0.49183(10) 0.77763(15) 0.0252(3) Uani 1 1 d . . . . .
H12 H 0.439550 0.462356 0.839862 0.030 Uiso 1 1 calc R U . . .
C13 C 0.47848(15) 0.56774(11) 0.77585(19) 0.0349(5) Uani 1 1 d D . . . .
C14 C 0.47072(15) 0.61252(11) 0.6861(2) 0.0391(6) Uani 1 1 d . . . . .
H14 H 0.500054 0.664478 0.685419 0.047 Uiso 1 1 calc R U . . .
C15 C 0.42032(15) 0.58114(10) 0.59836(18) 0.0314(4) Uani 1 1 d . . . . .
H15 H 0.414639 0.611422 0.536807 0.038 Uiso 1 1 calc R U . . .
C16 C 0.37719(13) 0.50407(9) 0.59992(13) 0.0193(3) Uani 1 1 d . . . . .
C17 C 0.32559(13) 0.46588(10) 0.50947(13) 0.0205(3) Uani 1 1 d . . . . .
C18 C 0.31262(18) 0.49778(14) 0.41057(16) 0.0373(5) Uani 1 1 d . . . . .
H18 H 0.338766 0.549497 0.397519 0.045 Uiso 1 1 calc R U . . .
C19 C 0.2622(2) 0.45469(19) 0.33185(16) 0.0534(8) Uani 1 1 d . . . . .
H19 H 0.252156 0.476575 0.264742 0.064 Uiso 1 1 calc R U . . .
C20 C 0.2266(2) 0.37984(18) 0.35182(17) 0.0509(7) Uani 1 1 d . . . . .
H20 H 0.192270 0.348890 0.298466 0.061 Uiso 1 1 calc R U . . .
C21 C 0.24117(16) 0.34984(13) 0.44993(15) 0.0327(4) Uani 1 1 d . . . . .
H21 H 0.216584 0.297733 0.463053 0.039 Uiso 1 1 calc R U . . .
C22 C 0.5443(7) 0.6055(7) 0.8548(12) 0.0283(18) Uani 0.48(4) 1 d D . P B 1
H22 H 0.557353 0.574859 0.915397 0.034 Uiso 0.48(4) 1 calc R U P B 1
O1 O 0.5860(5) 0.6696(6) 0.8575(16) 0.037(2) Uani 0.48(4) 1 d D . P B 1
C22B C 0.5290(9) 0.5905(6) 0.8848(11) 0.0273(18) Uani 0.52(4) 1 d D . P B 2
H22B H 0.520885 0.556000 0.941535 0.033 Uiso 0.52(4) 1 calc R U P B 2
O1B O 0.5791(5) 0.6529(7) 0.8969(12) 0.035(2) Uani 0.52(4) 1 d D . P B 2
N31 N 0.46187(10) 0.30362(7) 0.63704(10) 0.0146(2) Uani 1 1 d . . . . .
C32 C 0.46737(13) 0.25283(9) 0.55772(13) 0.0193(3) Uani 1 1 d . . . . .
H32 H 0.401635 0.240932 0.518049 0.023 Uiso 1 1 calc R U . . .
C33 C 0.56540(14) 0.21727(10) 0.53185(14) 0.0242(3) Uani 1 1 d . . . . .
H33 H 0.566607 0.182233 0.474828 0.029 Uiso 1 1 calc R U . . .
C34 C 0.66160(14) 0.23328(10) 0.58985(14) 0.0235(3) Uani 1 1 d . . . . .
H34 H 0.729573 0.209223 0.573759 0.028 Uiso 1 1 calc R U . . .
C35 C 0.65640(13) 0.28518(10) 0.67188(13) 0.0208(3) Uani 1 1 d . . . . .
H35 H 0.720981 0.297197 0.713183 0.025 Uiso 1 1 calc R U . . .
C36 C 0.55580(12) 0.31942(9) 0.69303(12) 0.0171(3) Uani 1 1 d . . . . .
H36 H 0.552991 0.355311 0.749022 0.020 Uiso 1 1 calc R U . . .
C99 C 0.1746(6) 0.5301(5) 0.0254(6) 0.0309(16) Uani 0.507(4) 1 d D . P C 1
F1 F 0.1199(3) 0.5031(3) 0.1043(3) 0.0689(14) Uani 0.507(4) 1 d D . P C 1
F2 F 0.0993(5) 0.5488(4) -0.0483(4) 0.0504(14) Uani 0.507(4) 1 d D . P C 1
F3 F 0.2303(4) 0.46852(19) -0.0098(3) 0.0562(11) Uani 0.507(4) 1 d D . P C 1
S1 S 0.2682(3) 0.60960(18) 0.0614(3) 0.0217(5) Uani 0.507(4) 1 d D . P C 1
O2 O 0.1969(3) 0.6647(2) 0.1096(3) 0.0367(8) Uani 0.507(4) 1 d D . P C 1
O3 O 0.3063(3) 0.6359(2) -0.0347(3) 0.0513(11) Uani 0.507(4) 1 d D . P C 1
O4 O 0.3460(3) 0.5710(2) 0.1297(3) 0.0354(9) Uani 0.507(4) 1 d D . P C 1
C99B C 0.1478(6) 0.5436(4) 0.0208(6) 0.0264(14) Uani 0.493(4) 1 d D . P C 2
F1B F 0.0700(2) 0.5643(3) 0.0845(2) 0.0542(11) Uani 0.493(4) 1 d D . P C 2
F2B F 0.1153(6) 0.5656(3) -0.0745(4) 0.0359(11) Uani 0.493(4) 1 d D . P C 2
F3B F 0.1587(4) 0.46658(17) 0.0235(4) 0.0654(14) Uani 0.493(4) 1 d D . P C 2
S1B S 0.2776(3) 0.5913(2) 0.0576(3) 0.0261(6) Uani 0.493(4) 1 d D . P C 2
O2B O 0.2489(5) 0.6734(2) 0.0567(5) 0.081(2) Uani 0.493(4) 1 d D . P C 2
O3B O 0.3475(3) 0.5668(5) -0.0211(3) 0.103(3) Uani 0.493(4) 1 d D . P C 2
O4B O 0.3066(3) 0.5621(2) 0.1590(3) 0.0317(8) Uani 0.493(4) 1 d D . P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C11 2.0470(15) . ?
Ru1 N1 2.0823(14) . ?
Ru1 N31 2.1143(13) . ?
Ru1 C6 2.1685(16) . ?
Ru1 C5 2.1930(19) . ?
Ru1 C1 2.1933(16) . ?
Ru1 C4 2.2255(19) . ?
Ru1 C2 2.2635(18) . ?
Ru1 C3 2.2829(18) . ?
N1 C21 1.347(2) . ?
N1 C17 1.359(2) . ?
C1 C6 1.400(3) . ?
C1 C2 1.438(3) . ?
C1 C7 1.519(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.422(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.405(3) . ?
C4 C10B 1.483(10) . ?
C4 C10 1.549(7) . ?
C5 C6 1.438(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C9 1.524(3) . ?
C7 C8 1.527(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11 C12 1.394(2) . ?
C11 C16 1.411(2) . ?
C12 C13 1.396(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.391(4) . ?
C13 C22 1.422(8) . ?
C13 C22B 1.564(9) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.407(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.457(2) . ?
C17 C18 1.396(2) . ?
C18 C19 1.377(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.368(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.376(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O1 1.198(7) . ?
C22 H22 0.9500 . ?
C22B O1B 1.225(7) . ?
C22B H22B 0.9500 . ?
N31 C32 1.347(2) . ?
N31 C36 1.3486(19) . ?
C32 C33 1.386(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.385(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.388(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C99 F1 1.328(8) . ?
C99 F2 1.330(7) . ?
C99 F3 1.335(7) . ?
C99 S1 1.808(8) . ?
S1 O3 1.421(5) . ?
S1 O4 1.424(5) . ?
S1 O2 1.434(4) . ?
C99B F3B 1.312(7) . ?
C99B F1B 1.328(8) . ?
C99B F2B 1.336(8) . ?
C99B S1B 1.812(7) . ?
S1B O3B 1.418(5) . ?
S1B O4B 1.436(5) . ?
S1B O2B 1.436(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 Ru1 N1 78.10(6) . . ?
C11 Ru1 N31 87.90(5) . . ?
N1 Ru1 N31 87.00(5) . . ?
C11 Ru1 C6 90.78(7) . . ?
N1 Ru1 C6 118.15(6) . . ?
N31 Ru1 C6 153.96(6) . . ?
C11 Ru1 C5 95.69(8) . . ?
N1 Ru1 C5 156.35(6) . . ?
N31 Ru1 C5 115.81(6) . . ?
C6 Ru1 C5 38.50(7) . . ?
C11 Ru1 C1 113.57(6) . . ?
N1 Ru1 C1 92.94(6) . . ?
N31 Ru1 C1 158.07(6) . . ?
C6 Ru1 C1 37.43(8) . . ?
C5 Ru1 C1 68.40(8) . . ?
C11 Ru1 C4 124.17(9) . . ?
N1 Ru1 C4 157.61(9) . . ?
N31 Ru1 C4 91.27(6) . . ?
C6 Ru1 C4 68.17(7) . . ?
C5 Ru1 C4 37.06(9) . . ?
C1 Ru1 C4 80.50(7) . . ?
C11 Ru1 C2 150.84(6) . . ?
N1 Ru1 C2 95.89(8) . . ?
N31 Ru1 C2 120.56(6) . . ?
C6 Ru1 C2 66.68(8) . . ?
C5 Ru1 C2 78.36(10) . . ?
C1 Ru1 C2 37.61(7) . . ?
C4 Ru1 C2 65.95(10) . . ?
C11 Ru1 C3 160.66(9) . . ?
N1 Ru1 C3 121.14(9) . . ?
N31 Ru1 C3 94.69(6) . . ?
C6 Ru1 C3 78.52(8) . . ?
C5 Ru1 C3 65.93(10) . . ?
C1 Ru1 C3 66.66(7) . . ?
C4 Ru1 C3 36.74(10) . . ?
C2 Ru1 C3 35.59(8) . . ?
C21 N1 C17 119.08(16) . . ?
C21 N1 Ru1 123.50(14) . . ?
C17 N1 Ru1 117.40(11) . . ?
C6 C1 C2 118.33(18) . . ?
C6 C1 C7 123.30(16) . . ?
C2 C1 C7 118.37(19) . . ?
C6 C1 Ru1 70.32(9) . . ?
C2 C1 Ru1 73.84(10) . . ?
C7 C1 Ru1 126.71(12) . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 Ru1 72.97(11) . . ?
C1 C2 Ru1 68.54(10) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
Ru1 C2 H2 131.9 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 Ru1 71.44(11) . . ?
C4 C3 Ru1 69.43(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
Ru1 C3 H3 132.6 . . ?
C5 C4 C3 119.1(2) . . ?
C5 C4 C10B 134.7(7) . . ?
C3 C4 C10B 106.1(7) . . ?
C5 C4 C10 114.5(7) . . ?
C3 C4 C10 126.4(7) . . ?
C5 C4 Ru1 70.21(10) . . ?
C3 C4 Ru1 73.82(12) . . ?
C10B C4 Ru1 129.1(5) . . ?
C10 C4 Ru1 128.0(3) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 Ru1 72.73(12) . . ?
C6 C5 Ru1 69.83(10) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
Ru1 C5 H5 130.0 . . ?
C1 C6 C5 120.62(18) . . ?
C1 C6 Ru1 72.25(10) . . ?
C5 C6 Ru1 71.67(10) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
Ru1 C6 H6 128.7 . . ?
C1 C7 C9 113.42(16) . . ?
C1 C7 C8 109.26(18) . . ?
C9 C7 C8 111.64(16) . . ?
C1 C7 H7 107.4 . . ?
C9 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C10B H10D 109.5 . . ?
C4 C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C4 C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C12 C11 C16 116.69(15) . . ?
C12 C11 Ru1 127.69(13) . . ?
C16 C11 Ru1 115.61(11) . . ?
C11 C12 C13 121.75(19) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C14 C13 C12 120.38(19) . . ?
C14 C13 C22 111.9(8) . . ?
C12 C13 C22 127.4(7) . . ?
C14 C13 C22B 129.2(6) . . ?
C12 C13 C22B 110.4(6) . . ?
C15 C14 C13 119.62(17) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 119.87(19) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C11 121.65(17) . . ?
C15 C16 C17 123.14(17) . . ?
C11 C16 C17 115.21(14) . . ?
N1 C17 C18 119.86(18) . . ?
N1 C17 C16 113.56(14) . . ?
C18 C17 C16 126.58(18) . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 118.9(2) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 119.4(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
N1 C21 C20 122.4(2) . . ?
N1 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
O1 C22 C13 130.6(8) . . ?
O1 C22 H22 114.7 . . ?
C13 C22 H22 114.7 . . ?
O1B C22B C13 120.0(6) . . ?
O1B C22B H22B 120.0 . . ?
C13 C22B H22B 120.0 . . ?
C32 N31 C36 118.02(13) . . ?
C32 N31 Ru1 120.37(10) . . ?
C36 N31 Ru1 121.44(10) . . ?
N31 C32 C33 122.42(15) . . ?
N31 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
C34 C33 C32 119.41(16) . . ?
C34 C33 H33 120.3 . . ?
C32 C33 H33 120.3 . . ?
C33 C34 C35 118.46(15) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 H34 120.8 . . ?
C34 C35 C36 119.25(15) . . ?
C34 C35 H35 120.4 . . ?
C36 C35 H35 120.4 . . ?
N31 C36 C35 122.43(15) . . ?
N31 C36 H36 118.8 . . ?
C35 C36 H36 118.8 . . ?
F1 C99 F2 106.7(6) . . ?
F1 C99 F3 105.8(6) . . ?
F2 C99 F3 106.3(6) . . ?
F1 C99 S1 112.7(5) . . ?
F2 C99 S1 114.2(6) . . ?
F3 C99 S1 110.6(5) . . ?
O3 S1 O4 117.3(4) . . ?
O3 S1 O2 113.8(3) . . ?
O4 S1 O2 114.9(3) . . ?
O3 S1 C99 103.3(4) . . ?
O4 S1 C99 102.0(3) . . ?
O2 S1 C99 102.5(3) . . ?
F3B C99B F1B 108.6(6) . . ?
F3B C99B F2B 109.2(6) . . ?
F1B C99B F2B 108.4(5) . . ?
F3B C99B S1B 110.6(4) . . ?
F1B C99B S1B 110.4(5) . . ?
F2B C99B S1B 109.6(6) . . ?
O3B S1B O4B 115.5(4) . . ?
O3B S1B O2B 115.5(5) . . ?
O4B S1B O2B 113.0(4) . . ?
O3B S1B C99B 102.6(4) . . ?
O4B S1B C99B 105.1(4) . . ?
O2B S1B C99B 103.0(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
_geom_hbond_publ_flag
C21 H21 O2B 0.95 2.17 2.994(4) 145.1 2_545 yes
C32 H32 O2 0.95 2.38 3.244(4) 151.0 2_545 yes
C32 H32 O2B 0.95 2.33 3.243(4) 162.2 2_545 yes
C35 H35 O2 0.95 2.55 3.387(4) 147.3 3_666 yes
C36 H36 O4 0.95 2.32 3.149(4) 146.1 3_666 yes
C36 H36 O4B 0.95 2.47 3.196(4) 133.3 3_666 yes

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_B1_0msp_a
_database_code_depnum_ccdc_archive 'CCDC 1879834'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 Cl N2 O Ru'
_chemical_formula_weight         441.91

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

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

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

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

_cell_length_a                   10.7146(5)
_cell_length_b                   13.1262(6)
_cell_length_c                   12.7262(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.545(2)
_cell_angle_gamma                90
_cell_volume                     1788.07(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9024
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.56

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.036
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6845
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS-2014/5
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'high brilliance microfocus sealed tube '
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω-scans and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            140718
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.230
_diffrn_reflns_theta_max         30.622
_diffrn_reflns_theta_full        29.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5503
_reflns_number_gt                5000
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'APEX3 2016.1-0 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0202P)²+1.4705P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5503
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0219
_refine_ls_wR_factor_ref         0.0494
_refine_ls_wR_factor_gt          0.0475
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.49128(2) 0.21793(2) 0.26833(2) 0.00936(3) Uani 1 1 d . . . . .
Cl1 Cl 0.59480(3) 0.16933(3) 0.11005(3) 0.01480(7) Uani 1 1 d . . . . .
N1 N 0.65921(11) 0.27930(9) 0.32352(9) 0.0115(2) Uani 1 1 d . . . . .
N2 N 0.67785(11) 0.38017(9) 0.30373(9) 0.0113(2) Uani 1 1 d . . . . .
C1 C 0.42724(13) 0.20392(10) 0.42823(11) 0.0126(2) Uani 1 1 d . . . . .
C2 C 0.47736(13) 0.10629(11) 0.40111(11) 0.0139(3) Uani 1 1 d . . . . .
H2 H 0.539295 0.075387 0.446351 0.017 Uiso 1 1 calc R U . . .
C3 C 0.43635(14) 0.05650(11) 0.30953(11) 0.0164(3) Uani 1 1 d . . . . .
H3 H 0.471176 -0.007692 0.292653 0.020 Uiso 1 1 calc R U . . .
C4 C 0.34205(14) 0.10088(11) 0.24015(11) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.28859(13) 0.19405(12) 0.26827(12) 0.0173(3) Uani 1 1 d . . . . .
H5 H 0.223499 0.222894 0.224726 0.021 Uiso 1 1 calc R U . . .
C6 C 0.33137(13) 0.24597(11) 0.36204(12) 0.0151(3) Uani 1 1 d . . . . .
H6 H 0.294906 0.309282 0.379869 0.018 Uiso 1 1 calc R U . . .
C7 C 0.47859(14) 0.25646(12) 0.52683(11) 0.0171(3) Uani 1 1 d . . . . .
H7 H 0.570127 0.241599 0.533612 0.021 Uiso 1 1 calc R U . . .
C8 C 0.46296(19) 0.37213(13) 0.52447(14) 0.0288(4) Uani 1 1 d . . . . .
H8A H 0.496376 0.399222 0.459692 0.043 Uiso 1 1 calc R U . . .
H8B H 0.508389 0.402108 0.585451 0.043 Uiso 1 1 calc R U . . .
H8C H 0.374104 0.389275 0.526755 0.043 Uiso 1 1 calc R U . . .
C9 C 0.41826(15) 0.21123(12) 0.62357(12) 0.0197(3) Uani 1 1 d . . . . .
H9A H 0.330649 0.232584 0.624175 0.030 Uiso 1 1 calc R U . . .
H9B H 0.462961 0.235521 0.687594 0.030 Uiso 1 1 calc R U . . .
H9C H 0.422647 0.136715 0.620684 0.030 Uiso 1 1 calc R U . . .
C10 C 0.29960(18) 0.04607(14) 0.14157(13) 0.0290(4) Uani 1 1 d . . . . .
H10A H 0.237149 -0.005309 0.158282 0.043 Uiso 1 1 calc R U . . .
H10B H 0.371281 0.012684 0.110945 0.043 Uiso 1 1 calc R U . . .
H10C H 0.262616 0.095001 0.091043 0.043 Uiso 1 1 calc R U . . .
C11 C 0.48467(12) 0.36282(10) 0.20751(10) 0.0107(2) Uani 1 1 d . . . . .
C12 C 0.39633(12) 0.40547(10) 0.13721(10) 0.0118(2) Uani 1 1 d . . . . .
H12 H 0.328968 0.364617 0.110467 0.014 Uiso 1 1 calc R U . . .
C13 C 0.40431(12) 0.50746(10) 0.10479(11) 0.0119(2) Uani 1 1 d . . . . .
C14 C 0.49955(13) 0.57018(10) 0.14569(11) 0.0131(2) Uani 1 1 d . . . . .
H14 H 0.501646 0.640086 0.126517 0.016 Uiso 1 1 calc R U . . .
C15 C 0.59136(13) 0.53052(10) 0.21445(11) 0.0128(2) Uani 1 1 d . . . . .
H15 H 0.657313 0.572016 0.242670 0.015 Uiso 1 1 calc R U . . .
C16 C 0.58335(12) 0.42784(10) 0.24058(10) 0.0109(2) Uani 1 1 d . . . . .
C17 C 0.78728(13) 0.41255(11) 0.35011(11) 0.0148(3) Uani 1 1 d . . . . .
H17 H 0.820623 0.479521 0.347543 0.018 Uiso 1 1 calc R U . . .
C18 C 0.84089(13) 0.33014(11) 0.40156(11) 0.0158(3) Uani 1 1 d . . . . .
H8 H 0.918081 0.328663 0.441255 0.019 Uiso 1 1 calc R U . . .
C19 C 0.75765(13) 0.24862(11) 0.38313(11) 0.0132(2) Uani 1 1 d . . . . .
H19 H 0.769765 0.181417 0.409345 0.016 Uiso 1 1 calc R U . . .
C20 C 0.31707(13) 0.54815(11) 0.02265(11) 0.0140(3) Uani 1 1 d . . . . .
H20 H 0.326118 0.617442 0.002836 0.017 Uiso 1 1 calc R U . . .
O1 O 0.23420(10) 0.49897(8) -0.02152(9) 0.0186(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C11 2.0534(13) . ?
Ru1 N1 2.0657(12) . ?
Ru1 C6 2.1622(14) . ?
Ru1 C1 2.1840(13) . ?
Ru1 C5 2.1942(14) . ?
Ru1 C4 2.2349(14) . ?
Ru1 C2 2.2467(13) . ?
Ru1 C3 2.2668(14) . ?
Ru1 Cl1 2.4275(4) . ?
N1 C19 1.3339(17) . ?
N1 N2 1.3642(16) . ?
N2 C17 1.3573(17) . ?
N2 C16 1.4108(17) . ?
C1 C6 1.412(2) . ?
C1 C2 1.4374(19) . ?
C1 C7 1.514(2) . ?
C2 C3 1.390(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.435(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(2) . ?
C4 C10 1.499(2) . ?
C5 C6 1.432(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.528(2) . ?
C7 C9 1.535(2) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.3908(19) . ?
C11 C16 1.4084(18) . ?
C12 C13 1.4047(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3939(19) . ?
C13 C20 1.4713(19) . ?
C14 C15 1.388(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.3918(18) . ?
C15 H15 0.9500 . ?
C17 C18 1.377(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.406(2) . ?
C18 H8 0.9500 . ?
C19 H19 0.9500 . ?
C20 O1 1.2151(18) . ?
C20 H20 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
C11 Ru1 N1 77.40(5) . . ?
C11 Ru1 C6 92.02(5) . . ?
N1 Ru1 C6 116.47(5) . . ?
C11 Ru1 C1 114.97(5) . . ?
N1 Ru1 C1 91.20(5) . . ?
C6 Ru1 C1 37.90(5) . . ?
C11 Ru1 C5 96.58(5) . . ?
N1 Ru1 C5 154.55(5) . . ?
C6 Ru1 C5 38.37(6) . . ?
C1 Ru1 C5 68.68(5) . . ?
C11 Ru1 C4 124.32(5) . . ?
N1 Ru1 C4 158.24(5) . . ?
C6 Ru1 C4 68.08(6) . . ?
C1 Ru1 C4 80.76(5) . . ?
C5 Ru1 C4 36.94(6) . . ?
C11 Ru1 C2 152.29(5) . . ?
N1 Ru1 C2 94.85(5) . . ?
C6 Ru1 C2 67.38(5) . . ?
C1 Ru1 C2 37.83(5) . . ?
C5 Ru1 C2 78.95(5) . . ?
C4 Ru1 C2 66.51(5) . . ?
C11 Ru1 C3 161.44(5) . . ?
N1 Ru1 C3 121.14(5) . . ?
C6 Ru1 C3 79.12(5) . . ?
C1 Ru1 C3 67.06(5) . . ?
C5 Ru1 C3 66.38(6) . . ?
C4 Ru1 C3 37.18(5) . . ?
C2 Ru1 C3 35.88(5) . . ?
C11 Ru1 Cl1 86.56(4) . . ?
N1 Ru1 Cl1 87.79(3) . . ?
C6 Ru1 Cl1 154.81(4) . . ?
C1 Ru1 Cl1 157.68(4) . . ?
C5 Ru1 Cl1 116.80(4) . . ?
C4 Ru1 Cl1 92.07(4) . . ?
C2 Ru1 Cl1 120.05(4) . . ?
C3 Ru1 Cl1 94.54(4) . . ?
C19 N1 N2 106.23(11) . . ?
C19 N1 Ru1 136.93(10) . . ?
N2 N1 Ru1 116.63(8) . . ?
C17 N2 N1 110.76(11) . . ?
C17 N2 C16 133.88(12) . . ?
N1 N2 C16 115.36(11) . . ?
C6 C1 C2 118.36(13) . . ?
C6 C1 C7 123.00(13) . . ?
C2 C1 C7 118.64(13) . . ?
C6 C1 Ru1 70.21(8) . . ?
C2 C1 Ru1 73.45(8) . . ?
C7 C1 Ru1 128.05(9) . . ?
C3 C2 C1 120.85(13) . . ?
C3 C2 Ru1 72.85(8) . . ?
C1 C2 Ru1 68.72(7) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
Ru1 C2 H2 131.8 . . ?
C2 C3 C4 120.83(13) . . ?
C2 C3 Ru1 71.27(8) . . ?
C4 C3 Ru1 70.20(8) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
Ru1 C3 H3 131.9 . . ?
C5 C4 C3 118.74(13) . . ?
C5 C4 C10 121.29(15) . . ?
C3 C4 C10 119.94(15) . . ?
C5 C4 Ru1 69.95(8) . . ?
C3 C4 Ru1 72.62(8) . . ?
C10 C4 Ru1 130.73(11) . . ?
C4 C5 C6 120.54(13) . . ?
C4 C5 Ru1 73.11(8) . . ?
C6 C5 Ru1 69.61(8) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
Ru1 C5 H5 130.1 . . ?
C1 C6 C5 120.58(13) . . ?
C1 C6 Ru1 71.89(8) . . ?
C5 C6 Ru1 72.03(8) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
Ru1 C6 H6 128.7 . . ?
C1 C7 C8 113.64(13) . . ?
C1 C7 C9 109.76(12) . . ?
C8 C7 C9 110.51(13) . . ?
C1 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C9 C7 H7 107.6 . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 115.39(12) . . ?
C12 C11 Ru1 128.78(10) . . ?
C16 C11 Ru1 115.83(10) . . ?
C11 C12 C13 121.60(12) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 120.42(13) . . ?
C14 C13 C20 118.85(12) . . ?
C12 C13 C20 120.64(12) . . ?
C15 C14 C13 120.03(12) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 117.66(12) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C15 C16 C11 124.67(13) . . ?
C15 C16 N2 121.01(12) . . ?
C11 C16 N2 114.31(12) . . ?
N2 C17 C18 107.15(12) . . ?
N2 C17 H17 126.4 . . ?
C18 C17 H17 126.4 . . ?
C17 C18 C19 105.69(12) . . ?
C17 C18 H8 127.2 . . ?
C19 C18 H8 127.2 . . ?
N1 C19 C18 110.17(13) . . ?
N1 C19 H19 124.9 . . ?
C18 C19 H19 124.9 . . ?
O1 C20 C13 124.33(13) . . ?
O1 C20 H20 117.8 . . ?
C13 C20 H20 117.8 . . ?

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
_geom_hbond_publ_flag
C17 H17 Cl1 0.95 2.70 3.6273(15) 166.2 2_655 yes
C18 H8 Cl1 0.95 2.80 3.7149(15) 162.0 4_666 yes
C19 H19 O1 0.95 2.56 3.4821(18) 163.6 4_666 yes

_refine_diff_density_max         0.479
_refine_diff_density_min         -0.818
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_Ru150326sp
_database_code_depnum_ccdc_archive 'CCDC 1879833'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H22 Cl N O Ru'
_chemical_formula_weight         452.92

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.1703(6)
_cell_length_b                   13.1012(6)
_cell_length_c                   12.5663(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.3829(17)
_cell_angle_gamma                90
_cell_volume                     1838.97(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9807
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      30.55

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    1.009
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7756
_exptl_absorpt_correction_T_max  0.8622
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'high brilliance microfocus sealed tube '
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'w-scans and phi-scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            60483
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         30.604
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5647
_reflns_number_gt                5043
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 2017.3 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+1.2814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5647
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0209
_refine_ls_wR_factor_ref         0.0489
_refine_ls_wR_factor_gt          0.0473
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.97511(2) 0.23153(2) 0.75780(2) 0.00877(3) Uani 1 1 d . . . . .
Cl1 Cl 1.07647(3) 0.18210(3) 0.59537(3) 0.01433(7) Uani 1 1 d . . . . .
N1 N 1.13576(10) 0.30105(9) 0.80448(9) 0.0106(2) Uani 1 1 d . . . . .
C1 C 0.92057(12) 0.21255(10) 0.92375(10) 0.0118(2) Uani 1 1 d . . . . .
C2 C 0.82567(12) 0.25665(10) 0.86423(11) 0.0139(3) Uani 1 1 d . . . . .
H2 H 0.799462 0.327951 0.880309 0.017 Uiso 1 1 calc R U . . .
C3 C 0.78124(12) 0.20667(11) 0.77095(11) 0.0159(3) Uani 1 1 d . . . . .
H3 H 0.725986 0.244664 0.722133 0.019 Uiso 1 1 calc R U . . .
C4 C 0.83084(13) 0.11425(11) 0.73656(11) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.92295(13) 0.06780(11) 0.79993(11) 0.0152(3) Uani 1 1 d . . . . .
H5 H 0.970076 0.010363 0.768713 0.018 Uiso 1 1 calc R U . . .
C6 C 0.96563(12) 0.11459(10) 0.89174(11) 0.0127(2) Uani 1 1 d . . . . .
H6 H 1.042007 0.089307 0.924272 0.015 Uiso 1 1 calc R U . . .
C7 C 0.97371(13) 0.26208(11) 1.02213(11) 0.0156(3) Uani 1 1 d . . . . .
H7 H 1.061936 0.249169 1.021385 0.019 Uiso 1 1 calc R U . . .
C8 C 0.92344(14) 0.21163(12) 1.12261(11) 0.0193(3) Uani 1 1 d . . . . .
H8A H 0.838289 0.228345 1.129144 0.029 Uiso 1 1 calc R U . . .
H8B H 0.966922 0.236912 1.185269 0.029 Uiso 1 1 calc R U . . .
H28C H 0.933008 0.137438 1.117582 0.029 Uiso 1 1 calc R U . . .
C9 C 0.95532(18) 0.37720(12) 1.02587(13) 0.0289(4) Uani 1 1 d . . . . .
H9A H 0.983360 0.407684 0.959319 0.043 Uiso 1 1 calc R U . . .
H29B H 1.000733 0.405820 1.085819 0.043 Uiso 1 1 calc R U . . .
H29C H 0.870029 0.392182 1.034861 0.043 Uiso 1 1 calc R U . . .
C10 C 0.78435(17) 0.06087(14) 0.63894(13) 0.0268(4) Uani 1 1 d . . . . .
H10A H 0.724760 0.009806 0.659605 0.040 Uiso 1 1 calc R U . . .
H10B H 0.850766 0.027102 0.602493 0.040 Uiso 1 1 calc R U . . .
H10C H 0.747197 0.110860 0.591031 0.040 Uiso 1 1 calc R U . . .
C11 C 0.95906(12) 0.37313(10) 0.69151(10) 0.0101(2) Uani 1 1 d . . . . .
C12 C 0.87064(12) 0.40705(10) 0.62058(10) 0.0111(2) Uani 1 1 d . . . . .
H12 H 0.809604 0.361212 0.598127 0.013 Uiso 1 1 calc R U . . .
C13 C 0.87040(12) 0.50743(10) 0.58199(10) 0.0110(2) Uani 1 1 d . . . . .
C14 C 0.95608(12) 0.57795(10) 0.61692(11) 0.0121(2) Uani 1 1 d . . . . .
H14 H 0.952560 0.646938 0.593817 0.015 Uiso 1 1 calc R U . . .
C15 C 1.04620(12) 0.54603(10) 0.68561(11) 0.0117(2) Uani 1 1 d . . . . .
H15 H 1.105231 0.593014 0.709681 0.014 Uiso 1 1 calc R U . . .
C16 C 1.04979(12) 0.44424(10) 0.71934(10) 0.0105(2) Uani 1 1 d . . . . .
C17 C 1.14958(12) 0.40187(10) 0.78114(10) 0.0105(2) Uani 1 1 d . . . . .
C18 C 1.25220(12) 0.45494(11) 0.81360(11) 0.0137(3) Uani 1 1 d . . . . .
H18 H 1.261508 0.524978 0.795909 0.016 Uiso 1 1 calc R U . . .
C19 C 1.33995(12) 0.40497(11) 0.87154(11) 0.0148(3) Uani 1 1 d . . . . .
H19 H 1.409220 0.440598 0.895285 0.018 Uiso 1 1 calc R U . . .
C20 C 1.32562(12) 0.30195(11) 0.89466(11) 0.0146(3) Uani 1 1 d . . . . .
H20 H 1.384964 0.266069 0.934161 0.018 Uiso 1 1 calc R U . . .
C21 C 1.22321(12) 0.25248(10) 0.85905(11) 0.0129(3) Uani 1 1 d . . . . .
H21 H 1.214270 0.181742 0.873617 0.016 Uiso 1 1 calc R U . . .
C22 C 0.78523(12) 0.54045(10) 0.49923(11) 0.0130(2) Uani 1 1 d . . . . .
H22 H 0.788538 0.609619 0.476752 0.016 Uiso 1 1 calc R U . . .
O1 O 0.71065(9) 0.48531(8) 0.45740(8) 0.0175(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C11 2.0410(13) . ?
Ru1 N1 2.0928(11) . ?
Ru1 C2 2.1711(14) . ?
Ru1 C1 2.1906(13) . ?
Ru1 C3 2.1973(14) . ?
Ru1 C4 2.2413(14) . ?
Ru1 C6 2.2789(13) . ?
Ru1 C5 2.2859(14) . ?
Ru1 Cl1 2.4287(3) . ?
N1 C21 1.3492(17) . ?
N1 C17 1.3621(17) . ?
C1 C2 1.416(2) . ?
C1 C6 1.4370(19) . ?
C1 C7 1.5139(19) . ?
C2 C3 1.429(2) . ?
C3 C4 1.401(2) . ?
C4 C5 1.433(2) . ?
C4 C10 1.502(2) . ?
C5 C6 1.388(2) . ?
C7 C9 1.523(2) . ?
C7 C8 1.535(2) . ?
C11 C12 1.3986(18) . ?
C11 C16 1.4186(18) . ?
C12 C13 1.4016(18) . ?
C13 C14 1.3988(19) . ?
C13 C22 1.4699(19) . ?
C14 C15 1.3863(19) . ?
C15 C16 1.3999(18) . ?
C16 C17 1.4636(18) . ?
C17 C18 1.3991(18) . ?
C18 C19 1.382(2) . ?
C19 C20 1.390(2) . ?
C20 C21 1.386(2) . ?
C22 O1 1.2192(17) . ?

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
C11 Ru1 N1 77.97(5) . . ?
C11 Ru1 C2 92.74(5) . . ?
N1 Ru1 C2 115.01(5) . . ?
C11 Ru1 C1 117.87(5) . . ?
N1 Ru1 C1 91.49(5) . . ?
C2 Ru1 C1 37.90(5) . . ?
C11 Ru1 C3 94.67(5) . . ?
N1 Ru1 C3 152.52(5) . . ?
C2 Ru1 C3 38.18(5) . . ?
C1 Ru1 C3 68.35(5) . . ?
C11 Ru1 C4 120.89(5) . . ?
N1 Ru1 C4 161.13(5) . . ?
C2 Ru1 C4 67.79(5) . . ?
C1 Ru1 C4 80.29(5) . . ?
C3 Ru1 C4 36.78(6) . . ?
C11 Ru1 C6 155.24(5) . . ?
N1 Ru1 C6 97.45(5) . . ?
C2 Ru1 C6 66.87(5) . . ?
C1 Ru1 C6 37.44(5) . . ?
C3 Ru1 C6 78.12(5) . . ?
C4 Ru1 C6 65.81(5) . . ?
C11 Ru1 C5 157.77(5) . . ?
N1 Ru1 C5 124.26(5) . . ?
C2 Ru1 C5 78.54(5) . . ?
C1 Ru1 C5 66.43(5) . . ?
C3 Ru1 C5 65.83(5) . . ?
C4 Ru1 C5 36.88(5) . . ?
C6 Ru1 C5 35.41(5) . . ?
C11 Ru1 Cl1 86.53(4) . . ?
N1 Ru1 Cl1 87.02(3) . . ?
C2 Ru1 Cl1 157.34(4) . . ?
C1 Ru1 Cl1 154.69(4) . . ?
C3 Ru1 Cl1 119.27(4) . . ?
C4 Ru1 Cl1 93.21(4) . . ?
C6 Ru1 Cl1 117.76(4) . . ?
C5 Ru1 Cl1 93.75(4) . . ?
C21 N1 C17 118.96(12) . . ?
C21 N1 Ru1 123.62(9) . . ?
C17 N1 Ru1 117.38(9) . . ?
C2 C1 C6 118.60(12) . . ?
C2 C1 C7 122.98(12) . . ?
C6 C1 C7 118.37(12) . . ?
C2 C1 Ru1 70.30(8) . . ?
C6 C1 Ru1 74.62(8) . . ?
C7 C1 Ru1 128.22(9) . . ?
C1 C2 C3 120.06(13) . . ?
C1 C2 Ru1 71.80(8) . . ?
C3 C2 Ru1 71.90(8) . . ?
C4 C3 C2 120.88(13) . . ?
C4 C3 Ru1 73.32(8) . . ?
C2 C3 Ru1 69.92(8) . . ?
C3 C4 C5 118.66(13) . . ?
C3 C4 C10 121.28(14) . . ?
C5 C4 C10 119.96(14) . . ?
C3 C4 Ru1 69.90(8) . . ?
C5 C4 Ru1 73.25(8) . . ?
C10 C4 Ru1 131.38(10) . . ?
C6 C5 C4 121.05(13) . . ?
C6 C5 Ru1 72.02(8) . . ?
C4 C5 Ru1 69.87(8) . . ?
C5 C6 C1 120.54(13) . . ?
C5 C6 Ru1 72.57(8) . . ?
C1 C6 Ru1 67.94(7) . . ?
C1 C7 C9 113.41(13) . . ?
C1 C7 C8 110.10(11) . . ?
C9 C7 C8 110.54(12) . . ?
C12 C11 C16 116.66(12) . . ?
C12 C11 Ru1 127.50(10) . . ?
C16 C11 Ru1 115.83(9) . . ?
C11 C12 C13 121.22(12) . . ?
C14 C13 C12 120.76(12) . . ?
C14 C13 C22 117.76(12) . . ?
C12 C13 C22 121.37(12) . . ?
C15 C14 C13 119.25(12) . . ?
C14 C15 C16 119.68(12) . . ?
C15 C16 C11 122.14(12) . . ?
C15 C16 C17 122.83(12) . . ?
C11 C16 C17 114.96(12) . . ?
N1 C17 C18 120.86(12) . . ?
N1 C17 C16 113.26(11) . . ?
C18 C17 C16 125.87(12) . . ?
C19 C18 C17 119.67(13) . . ?
C18 C19 C20 119.19(13) . . ?
C21 C20 C19 118.84(13) . . ?
N1 C21 C20 122.45(13) . . ?
O1 C22 C13 124.60(13) . . ?

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
_geom_hbond_publ_flag
C21 H21 O1 0.95 2.43 3.3547(17) 164.7 4_666 yes

_refine_diff_density_max         0.541
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_A1_aminoPYC_0msp_a
_database_code_depnum_ccdc_archive 'CCDC 1879832'
_audit_update_record             
;
2018-11-19 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H32 F3 N3 O4 Ru S'
_chemical_formula_weight         688.71

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.4821(7)
_cell_length_b                   14.3856(8)
_cell_length_c                   17.8111(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.525(2)
_cell_angle_gamma                90
_cell_volume                     2922.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9959
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      30.54

_exptl_crystal_description       lath
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             1408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.668
_shelx_estimated_absorpt_T_min   0.872
_shelx_estimated_absorpt_T_max   0.967
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS_2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'high brilliance microfocus sealed tube '
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω-scans and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            286523
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.824
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7260
_reflns_number_gt                6601
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 2017.3 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc.)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc.)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0231P)²+3.5068P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7260
_refine_ls_number_parameters     384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0635
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.52891(2) 0.76652(2) 0.25398(2) 0.01181(4) Uani 1 1 d . . . . .
O1 O 0.04405(12) 0.57431(11) 0.36186(9) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.45140(13) 0.82032(10) 0.15199(8) 0.0147(3) Uani 1 1 d . . . . .
C1 C 0.54917(15) 0.88745(13) 0.33087(10) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.54510(15) 0.80466(13) 0.37353(10) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.476624 0.794138 0.402514 0.020 Uiso 1 1 calc R U . . .
C3 C 0.62238(15) 0.72985(14) 0.36500(10) 0.0181(3) Uani 1 1 d . . . . .
H3 H 0.607247 0.668235 0.388007 0.022 Uiso 1 1 calc R U . . .
C4 C 0.70732(15) 0.73649(13) 0.31292(10) 0.0172(3) Uani 1 1 d . . . . .
C5 C 0.71656(15) 0.82001(13) 0.27210(10) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.764376 0.820820 0.228550 0.021 Uiso 1 1 calc R U . . .
C6 C 0.63520(16) 0.89193(13) 0.27912(10) 0.0170(3) Uani 1 1 d . . . . .
H6 H 0.629391 0.943193 0.240953 0.020 Uiso 1 1 calc R U . . .
C7 C 0.47077(17) 0.97036(14) 0.33960(11) 0.0218(4) Uani 1 1 d . . . . .
H7 H 0.457309 1.002365 0.289528 0.026 Uiso 1 1 calc R U . . .
C8 C 0.53533(19) 1.03828(15) 0.39591(12) 0.0270(4) Uani 1 1 d . . . . .
H8A H 0.607533 1.059246 0.376663 0.041 Uiso 1 1 calc R U . . .
H8B H 0.554846 1.007108 0.444644 0.041 Uiso 1 1 calc R U . . .
H8C H 0.484972 1.091982 0.402498 0.041 Uiso 1 1 calc R U . . .
C9 C 0.35096(19) 0.94536(18) 0.36359(16) 0.0385(6) Uani 1 1 d . . . . .
H9A H 0.303676 1.001865 0.365379 0.058 Uiso 1 1 calc R U . . .
H9B H 0.361430 0.916462 0.413734 0.058 Uiso 1 1 calc R U . . .
H9C H 0.310981 0.901734 0.327047 0.058 Uiso 1 1 calc R U . . .
C10 C 0.78321(17) 0.65446(15) 0.29896(12) 0.0239(4) Uani 1 1 d . . . . .
H10A H 0.812347 0.661241 0.249625 0.036 Uiso 1 1 calc R U . . .
H10B H 0.737046 0.597214 0.299542 0.036 Uiso 1 1 calc R U . . .
H10C H 0.849659 0.651478 0.338613 0.036 Uiso 1 1 calc R U . . .
C11 C 0.35648(15) 0.73342(13) 0.25753(10) 0.0145(3) Uani 1 1 d . . . . .
C12 C 0.30888(15) 0.68173(13) 0.31303(10) 0.0160(3) Uani 1 1 d . . . . .
H12 H 0.358682 0.660426 0.355816 0.019 Uiso 1 1 calc R U . . .
C13 C 0.18910(16) 0.66078(13) 0.30673(10) 0.0172(3) Uani 1 1 d . . . . .
C14 C 0.11373(16) 0.69386(14) 0.24583(11) 0.0193(4) Uani 1 1 d . . . . .
H14 H 0.032173 0.680944 0.242563 0.023 Uiso 1 1 calc R U . . .
C15 C 0.15791(16) 0.74542(13) 0.19030(11) 0.0192(4) Uani 1 1 d . . . . .
H15 H 0.106952 0.768374 0.148675 0.023 Uiso 1 1 calc R U . . .
C16 C 0.27862(15) 0.76382(12) 0.19560(10) 0.0144(3) Uani 1 1 d . . . . .
C17 C 0.33268(15) 0.81250(12) 0.13675(10) 0.0154(3) Uani 1 1 d . . . . .
C18 C 0.27481(17) 0.84583(13) 0.06879(10) 0.0198(4) Uani 1 1 d . . . . .
H18 H 0.191922 0.841548 0.058871 0.024 Uiso 1 1 calc R U . . .
C19 C 0.33984(18) 0.88519(14) 0.01610(11) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.301658 0.908786 -0.030096 0.027 Uiso 1 1 calc R U . . .
C20 C 0.46059(18) 0.89002(13) 0.03099(10) 0.0200(4) Uani 1 1 d . . . . .
H20 H 0.506467 0.915069 -0.005306 0.024 Uiso 1 1 calc R U . . .
C21 C 0.51322(16) 0.85768(12) 0.09974(10) 0.0173(3) Uani 1 1 d . . . . .
H21 H 0.596000 0.862002 0.110443 0.021 Uiso 1 1 calc R U . . .
C22 C 0.14516(17) 0.60020(14) 0.36385(11) 0.0204(4) Uani 1 1 d . . . . .
H22 H 0.199285 0.580031 0.404930 0.025 Uiso 1 1 calc R U . . .
N23 N 0.54057(13) 0.64134(10) 0.19221(8) 0.0153(3) Uani 1 1 d . . . . .
O24 O 0.46543(14) 0.71600(11) 0.51992(8) 0.0307(3) Uani 1 1 d . . . . .
C24 C 0.48684(16) 0.56150(13) 0.20817(11) 0.0188(4) Uani 1 1 d . . . . .
H24 H 0.439643 0.561944 0.248660 0.023 Uiso 1 1 calc R U . . .
O25 O 0.25341(14) 0.69832(14) 0.51718(10) 0.0416(4) Uani 1 1 d . . . . .
C25 C 0.49600(17) 0.47996(13) 0.16978(11) 0.0218(4) Uani 1 1 d . . . . .
H25 H 0.455868 0.426152 0.184034 0.026 Uiso 1 1 calc R U . . .
O26 O 0.37116(13) 0.73733(10) 0.63399(8) 0.0266(3) Uani 1 1 d . . . . .
C26 C 0.56471(16) 0.47545(13) 0.10919(11) 0.0194(4) Uani 1 1 d . . . . .
S27 S 0.36697(4) 0.69560(4) 0.56048(3) 0.01999(10) Uani 1 1 d . . . . .
C27 C 0.62413(16) 0.55814(13) 0.09429(11) 0.0192(4) Uani 1 1 d . . . . .
H27 H 0.674704 0.559183 0.055630 0.023 Uiso 1 1 calc R U . . .
C28 C 0.60915(15) 0.63699(13) 0.13539(10) 0.0176(3) Uani 1 1 d . . . . .
H28 H 0.649291 0.691754 0.123237 0.021 Uiso 1 1 calc R U . . .
N29 N 0.57178(16) 0.39712(12) 0.06800(10) 0.0269(4) Uani 1 1 d . . . . .
C30 C 0.5009(2) 0.31626(15) 0.08257(15) 0.0386(6) Uani 1 1 d . . . . .
H30A H 0.418424 0.334717 0.080505 0.058 Uiso 1 1 calc R U . . .
H30B H 0.527461 0.291183 0.132761 0.058 Uiso 1 1 calc R U . . .
H30C H 0.509175 0.268599 0.044225 0.058 Uiso 1 1 calc R U . . .
C31 C 0.6536(2) 0.39029(16) 0.01166(13) 0.0310(5) Uani 1 1 d . . . . .
H31A H 0.648114 0.328276 -0.011244 0.046 Uiso 1 1 calc R U . . .
H31B H 0.733521 0.400647 0.035806 0.046 Uiso 1 1 calc R U . . .
H31C H 0.634176 0.437339 -0.027563 0.046 Uiso 1 1 calc R U . . .
C99 C 0.38820(19) 0.57309(15) 0.58241(13) 0.0290(5) Uani 1 1 d . . . . .
F1 F 0.30520(15) 0.54181(10) 0.62351(10) 0.0515(4) Uani 1 1 d . . . . .
F2 F 0.38222(13) 0.52098(11) 0.52016(9) 0.0468(4) Uani 1 1 d . . . . .
F3 F 0.49180(14) 0.55713(10) 0.62188(9) 0.0448(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 C11 2.0443(17) . ?
Ru1 N1 2.0794(15) . ?
Ru1 N23 2.1224(15) . ?
Ru1 C2 2.1861(17) . ?
Ru1 C6 2.1955(18) . ?
Ru1 C3 2.2039(17) . ?
Ru1 C1 2.2099(18) . ?
Ru1 C4 2.2352(17) . ?
Ru1 C5 2.2760(18) . ?
O1 C22 1.216(2) . ?
N1 C21 1.345(2) . ?
N1 C17 1.364(2) . ?
C1 C2 1.416(3) . ?
C1 C6 1.427(2) . ?
C1 C7 1.513(3) . ?
C2 C3 1.414(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.424(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.415(3) . ?
C4 C10 1.504(3) . ?
C5 C6 1.409(3) . ?
C5 H5 1.0000 . ?
C6 H6 1.0000 . ?
C7 C9 1.529(3) . ?
C7 C8 1.530(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.397(2) . ?
C11 C16 1.408(2) . ?
C12 C13 1.400(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C22 1.472(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.404(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.457(2) . ?
C17 C18 1.398(2) . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
N23 C24 1.349(2) . ?
N23 C28 1.353(2) . ?
O24 S27 1.4394(15) . ?
C24 C25 1.368(3) . ?
C24 H24 0.9500 . ?
O25 S27 1.4380(16) . ?
C25 C26 1.409(3) . ?
C25 H25 0.9500 . ?
O26 S27 1.4361(15) . ?
C26 N29 1.352(2) . ?
C26 C27 1.411(3) . ?
S27 C99 1.816(2) . ?
C27 C28 1.371(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N29 C31 1.453(3) . ?
N29 C30 1.460(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C99 F3 1.331(3) . ?
C99 F2 1.334(3) . ?
C99 F1 1.343(2) . ?

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
C11 Ru1 N1 78.10(6) . . ?
C11 Ru1 N23 86.37(6) . . ?
N1 Ru1 N23 84.77(6) . . ?
C11 Ru1 C2 90.22(7) . . ?
N1 Ru1 C2 137.56(6) . . ?
N23 Ru1 C2 135.60(6) . . ?
C11 Ru1 C6 134.66(7) . . ?
N1 Ru1 C6 92.58(6) . . ?
N23 Ru1 C6 137.44(6) . . ?
C2 Ru1 C6 67.13(7) . . ?
C11 Ru1 C3 106.93(7) . . ?
N1 Ru1 C3 171.62(6) . . ?
N23 Ru1 C3 102.07(7) . . ?
C2 Ru1 C3 37.57(7) . . ?
C6 Ru1 C3 79.11(7) . . ?
C11 Ru1 C1 101.44(7) . . ?
N1 Ru1 C1 104.65(6) . . ?
N23 Ru1 C1 168.75(6) . . ?
C2 Ru1 C1 37.58(7) . . ?
C6 Ru1 C1 37.80(7) . . ?
C3 Ru1 C1 68.05(7) . . ?
C11 Ru1 C4 141.23(7) . . ?
N1 Ru1 C4 139.53(6) . . ?
N23 Ru1 C4 88.34(6) . . ?
C2 Ru1 C4 67.61(7) . . ?
C6 Ru1 C4 66.71(7) . . ?
C3 Ru1 C4 37.40(7) . . ?
C1 Ru1 C4 80.49(7) . . ?
C11 Ru1 C5 168.21(7) . . ?
N1 Ru1 C5 107.60(6) . . ?
N23 Ru1 C5 104.24(6) . . ?
C2 Ru1 C5 78.62(6) . . ?
C6 Ru1 C5 36.68(7) . . ?
C3 Ru1 C5 66.25(7) . . ?
C1 Ru1 C5 67.34(7) . . ?
C4 Ru1 C5 36.54(7) . . ?
C21 N1 C17 119.30(15) . . ?
C21 N1 Ru1 123.10(12) . . ?
C17 N1 Ru1 117.52(12) . . ?
C2 C1 C6 116.87(16) . . ?
C2 C1 C7 123.47(16) . . ?
C6 C1 C7 119.63(17) . . ?
C2 C1 Ru1 70.30(10) . . ?
C6 C1 Ru1 70.55(10) . . ?
C7 C1 Ru1 131.48(12) . . ?
C3 C2 C1 121.54(16) . . ?
C3 C2 Ru1 71.89(10) . . ?
C1 C2 Ru1 72.12(10) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
Ru1 C2 H2 118.7 . . ?
C2 C3 C4 120.25(17) . . ?
C2 C3 Ru1 70.53(10) . . ?
C4 C3 Ru1 72.50(10) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
Ru1 C3 H3 119.4 . . ?
C5 C4 C3 119.26(17) . . ?
C5 C4 C10 120.18(17) . . ?
C3 C4 C10 120.51(17) . . ?
C5 C4 Ru1 73.30(10) . . ?
C3 C4 Ru1 70.11(10) . . ?
C10 C4 Ru1 126.24(13) . . ?
C6 C5 C4 119.27(16) . . ?
C6 C5 Ru1 68.55(10) . . ?
C4 C5 Ru1 70.16(10) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
Ru1 C5 H5 119.2 . . ?
C5 C6 C1 122.59(17) . . ?
C5 C6 Ru1 74.77(10) . . ?
C1 C6 Ru1 71.64(10) . . ?
C5 C6 H6 118.3 . . ?
C1 C6 H6 118.3 . . ?
Ru1 C6 H6 118.3 . . ?
C1 C7 C9 114.08(17) . . ?
C1 C7 C8 108.73(16) . . ?
C9 C7 C8 110.56(17) . . ?
C1 C7 H7 107.7 . . ?
C9 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
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 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C16 117.07(16) . . ?
C12 C11 Ru1 127.15(13) . . ?
C16 C11 Ru1 115.75(13) . . ?
C11 C12 C13 121.17(16) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 120.45(17) . . ?
C14 C13 C22 120.63(17) . . ?
C12 C13 C22 118.87(17) . . ?
C15 C14 C13 119.74(17) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.63(17) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C11 121.88(16) . . ?
C15 C16 C17 122.72(16) . . ?
C11 C16 C17 115.36(15) . . ?
N1 C17 C18 120.66(16) . . ?
N1 C17 C16 113.23(15) . . ?
C18 C17 C16 126.05(17) . . ?
C19 C18 C17 119.16(18) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C20 C19 C18 119.77(17) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 118.70(17) . . ?
C21 C20 H20 120.7 . . ?
C19 C20 H20 120.7 . . ?
N1 C21 C20 122.36(17) . . ?
N1 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
O1 C22 C13 124.23(18) . . ?
O1 C22 H22 117.9 . . ?
C13 C22 H22 117.9 . . ?
C24 N23 C28 115.94(16) . . ?
C24 N23 Ru1 123.76(12) . . ?
C28 N23 Ru1 120.23(12) . . ?
N23 C24 C25 124.17(18) . . ?
N23 C24 H24 117.9 . . ?
C25 C24 H24 117.9 . . ?
C24 C25 C26 120.27(18) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
N29 C26 C25 121.83(18) . . ?
N29 C26 C27 122.71(18) . . ?
C25 C26 C27 115.46(17) . . ?
O26 S27 O25 114.34(10) . . ?
O26 S27 O24 115.18(9) . . ?
O25 S27 O24 116.18(10) . . ?
O26 S27 C99 102.70(10) . . ?
O25 S27 C99 103.49(11) . . ?
O24 S27 C99 102.24(10) . . ?
C28 C27 C26 120.28(17) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
N23 C28 C27 123.82(17) . . ?
N23 C28 H28 118.1 . . ?
C27 C28 H28 118.1 . . ?
C26 N29 C31 120.95(18) . . ?
C26 N29 C30 119.91(19) . . ?
C31 N29 C30 119.07(18) . . ?
N29 C30 H30A 109.5 . . ?
N29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N29 C31 H31A 109.5 . . ?
N29 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N29 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
F3 C99 F2 107.49(18) . . ?
F3 C99 F1 107.5(2) . . ?
F2 C99 F1 106.97(18) . . ?
F3 C99 S27 111.79(15) . . ?
F2 C99 S27 111.95(17) . . ?
F1 C99 S27 110.86(15) . . ?

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
_geom_hbond_publ_flag
C20 H20 O1 0.95 2.46 3.303(2) 148.2 4_675 yes

_refine_diff_density_max         1.477
_refine_diff_density_min         -0.536
_refine_diff_density_rms         0.067

