# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1989797'
loop_
_audit_author_name
_audit_author_address
'Victorio Cadierno'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;
#=======================================================================  

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H29 N2 O1 Cl1 F6 P1 Ru1 Sb1'
_chemical_formula_sum            'C16 H29 Cl F6 N2 O P Ru Sb'
_chemical_formula_weight         668.65

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 '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                   11.73940(10)
_cell_length_b                   14.7656(2)
_cell_length_c                   14.6955(2)
_cell_angle_alpha                90
_cell_angle_beta                 108.1720(10)
_cell_angle_gamma                90
_cell_volume                     2420.26(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7972
_cell_measurement_theta_min      4.2260
_cell_measurement_theta_max      69.4510

_exptl_crystal_description       plate
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    16.067
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.14384
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2640
_diffrn_reflns_number            12565
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.232
_diffrn_reflns_theta_max         69.594
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4476
_reflns_number_gt                4053
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0414P)²+2.3911P] 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         4476
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0782
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Sb1 Sb 0.78339(2) 0.85937(2) 0.07376(2) 0.03523(10) Uani 1 1 d . . . . .
Ru1 Ru 0.82616(2) 0.34424(2) 0.04130(2) 0.02142(9) Uani 1 1 d . . . . .
Cl1 Cl 0.74128(8) 0.46516(7) -0.06789(6) 0.0361(2) Uani 1 1 d . . . . .
P1 P 0.62919(8) 0.30647(7) 0.02092(6) 0.0271(2) Uani 1 1 d . . . . .
F3 F 0.9324(2) 0.8139(3) 0.0751(2) 0.0692(9) Uani 1 1 d . . . . .
N2 N 0.8014(3) 0.1598(2) -0.2094(2) 0.0343(8) Uani 1 1 d . . . . .
O1 O 0.6105(2) 0.2134(2) 0.0705(2) 0.0401(7) Uani 1 1 d . . . . .
F5 F 0.6351(2) 0.9020(3) 0.0772(3) 0.0707(9) Uani 1 1 d . . . . .
F2 F 0.8020(3) 0.7998(2) 0.1901(2) 0.0647(8) Uani 1 1 d . . . . .
C6 C 1.0056(3) 0.4146(3) 0.1082(3) 0.0313(9) Uani 1 1 d . . . . .
H6 H 1.0480 0.4582 0.0838 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5341(3) 0.2981(4) -0.1022(3) 0.0430(11) Uani 1 1 d . . . . .
H15A H 0.5670 0.2527 -0.1358 0.065 Uiso 1 1 calc R U . . .
H15B H 0.5308 0.3570 -0.1337 0.065 Uiso 1 1 calc R U . . .
H15C H 0.4532 0.2801 -0.1038 0.065 Uiso 1 1 calc R U . . .
C3 C 0.8851(3) 0.2845(3) 0.1842(2) 0.0282(8) Uani 1 1 d . . . . .
H3 H 0.8447 0.2409 0.2104 0.034 Uiso 1 1 calc R U . . .
C9 C 1.0023(5) 0.5819(5) 0.2453(6) 0.091(3) Uani 1 1 d . . . . .
H9A H 1.0040 0.5513 0.3049 0.136 Uiso 1 1 calc R U . . .
H9B H 0.9908 0.6471 0.2516 0.136 Uiso 1 1 calc R U . . .
H9C H 1.0784 0.5715 0.2325 0.136 Uiso 1 1 calc R U . . .
F1A F 0.8545(5) 0.9577(4) 0.1608(6) 0.057(2) Uiso 0.564(17) 1 d . . P A 1
F1B F 0.8557(7) 0.9639(6) 0.1191(9) 0.067(3) Uiso 0.436(17) 1 d . . P A 2
C12 C 0.8422(4) 0.1907(4) -0.2889(3) 0.0440(11) Uani 1 1 d . . . . .
H12A H 0.8174 0.2537 -0.3044 0.066 Uiso 1 1 calc R U . . .
H12B H 0.8065 0.1525 -0.3451 0.066 Uiso 1 1 calc R U . . .
H12C H 0.9298 0.1865 -0.2704 0.066 Uiso 1 1 calc R U . . .
N1 N 0.8124(3) 0.2650(2) -0.0767(2) 0.0304(7) Uani 1 1 d . . . . .
C5 C 0.9195(3) 0.4448(3) 0.1538(3) 0.0299(8) Uani 1 1 d . . . . .
C7 C 1.0271(3) 0.3236(3) 0.0995(3) 0.0295(8) Uani 1 1 d . . . . .
H7 H 1.0833 0.3057 0.0683 0.035 Uiso 1 1 calc R U . . .
C13 C 0.8181(5) 0.0633(4) -0.1848(4) 0.0564(13) Uani 1 1 d . . . . .
H13A H 0.9040 0.0494 -0.1611 0.085 Uiso 1 1 calc R U . . .
H13B H 0.7801 0.0267 -0.2419 0.085 Uiso 1 1 calc R U . . .
H13C H 0.7813 0.0492 -0.1351 0.085 Uiso 1 1 calc R U . . .
C11 C 0.8108(3) 0.2166(3) -0.1377(3) 0.0293(8) Uani 1 1 d . . . . .
C2 C 0.9663(3) 0.2551(3) 0.1367(3) 0.0297(8) Uani 1 1 d . . . . .
C16 C 0.6453(5) 0.1291(3) 0.0380(4) 0.0547(13) Uani 1 1 d . . . . .
H16A H 0.5913 0.1154 -0.0262 0.082 Uiso 1 1 calc R U . . .
H16B H 0.6405 0.0805 0.0821 0.082 Uiso 1 1 calc R U . . .
H16C H 0.7277 0.1338 0.0360 0.082 Uiso 1 1 calc R U . . .
C4 C 0.8630(3) 0.3784(3) 0.1934(2) 0.0285(8) Uani 1 1 d . . . . .
H4 H 0.8092 0.3964 0.2267 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5487(4) 0.3813(4) 0.0750(3) 0.0427(11) Uani 1 1 d . . . . .
H14A H 0.4652 0.3611 0.0592 0.064 Uiso 1 1 calc R U . . .
H14B H 0.5508 0.4429 0.0507 0.064 Uiso 1 1 calc R U . . .
H14C H 0.5860 0.3809 0.1447 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7799(4) 0.5678(4) 0.1758(4) 0.0528(12) Uani 1 1 d . . . . .
H10A H 0.7145 0.5446 0.1215 0.079 Uiso 1 1 calc R U . . .
H10B H 0.7729 0.6338 0.1794 0.079 Uiso 1 1 calc R U . . .
H10C H 0.7752 0.5404 0.2352 0.079 Uiso 1 1 calc R U . . .
C8 C 0.8988(4) 0.5442(3) 0.1622(4) 0.0426(10) Uani 1 1 d . . . . .
H8 H 0.9019 0.5740 0.1019 0.051 Uiso 1 1 calc R U . . .
C1 C 0.9920(4) 0.1567(3) 0.1275(3) 0.0411(10) Uani 1 1 d . . . . .
H1A H 1.0718 0.1421 0.1711 0.062 Uiso 1 1 calc R U . . .
H1B H 0.9893 0.1438 0.0614 0.062 Uiso 1 1 calc R U . . .
H1C H 0.9317 0.1200 0.1439 0.062 Uiso 1 1 calc R U . . .
F6 F 0.7116(3) 0.7554(3) 0.0089(3) 0.0799(11) Uani 1 1 d . . . . .
F4A F 0.7724(6) 0.9340(8) -0.0277(6) 0.077(2) Uiso 0.564(17) 1 d . . P A 1
F4B F 0.7579(7) 0.8950(8) -0.0548(7) 0.064(3) Uiso 0.436(17) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sb1 F1B 1.787(9) . ?
Sb1 F4A 1.826(7) . ?
Sb1 F6 1.864(3) . ?
Sb1 F5 1.867(3) . ?
Sb1 F3 1.868(3) . ?
Sb1 F2 1.874(3) . ?
Sb1 F4B 1.893(8) . ?
Sb1 F1A 1.943(7) . ?
Ru1 N1 2.056(3) . ?
Ru1 C3 2.181(3) . ?
Ru1 C4 2.199(3) . ?
Ru1 C2 2.228(4) . ?
Ru1 C5 2.238(4) . ?
Ru1 C7 2.266(3) . ?
Ru1 C6 2.278(4) . ?
Ru1 P1 2.3056(9) . ?
Ru1 Cl1 2.3996(10) . ?
P1 O1 1.602(3) . ?
P1 C14 1.793(4) . ?
P1 C15 1.809(4) . ?
N2 C11 1.324(5) . ?
N2 C12 1.467(5) . ?
N2 C13 1.469(6) . ?
O1 C16 1.438(6) . ?
C6 C7 1.381(6) . ?
C6 C5 1.446(5) . ?
C3 C2 1.414(5) . ?
C3 C4 1.424(6) . ?
C9 C8 1.534(8) . ?
N1 C11 1.142(5) . ?
C5 C4 1.407(5) . ?
C5 C8 1.499(6) . ?
C7 C2 1.440(5) . ?
C2 C1 1.498(6) . ?
C10 C8 1.511(6) . ?

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
F1B Sb1 F6 171.2(5) . . ?
F4A Sb1 F6 100.0(4) . . ?
F1B Sb1 F5 92.1(3) . . ?
F4A Sb1 F5 89.4(2) . . ?
F6 Sb1 F5 90.87(15) . . ?
F1B Sb1 F3 88.4(3) . . ?
F4A Sb1 F3 93.0(2) . . ?
F6 Sb1 F3 88.95(16) . . ?
F5 Sb1 F3 177.55(16) . . ?
F1B Sb1 F2 99.2(4) . . ?
F4A Sb1 F2 170.7(4) . . ?
F6 Sb1 F2 89.13(17) . . ?
F5 Sb1 F2 88.74(15) . . ?
F3 Sb1 F2 88.82(14) . . ?
F1B Sb1 F4B 92.3(4) . . ?
F6 Sb1 F4B 79.2(4) . . ?
F5 Sb1 F4B 94.3(3) . . ?
F3 Sb1 F4B 88.1(3) . . ?
F2 Sb1 F4B 168.0(4) . . ?
F4A Sb1 F1A 89.6(3) . . ?
F6 Sb1 F1A 170.1(3) . . ?
F5 Sb1 F1A 86.7(2) . . ?
F3 Sb1 F1A 93.1(2) . . ?
F2 Sb1 F1A 81.2(3) . . ?
N1 Ru1 C3 119.96(14) . . ?
N1 Ru1 C4 157.91(15) . . ?
C3 Ru1 C4 37.95(15) . . ?
N1 Ru1 C2 92.44(14) . . ?
C3 Ru1 C2 37.39(13) . . ?
C4 Ru1 C2 67.90(14) . . ?
N1 Ru1 C5 153.17(12) . . ?
C3 Ru1 C5 67.76(15) . . ?
C4 Ru1 C5 36.97(14) . . ?
C2 Ru1 C5 80.32(15) . . ?
N1 Ru1 C7 92.32(13) . . ?
C3 Ru1 C7 66.52(13) . . ?
C4 Ru1 C7 78.22(13) . . ?
C2 Ru1 C7 37.36(14) . . ?
C5 Ru1 C7 66.32(14) . . ?
N1 Ru1 C6 116.27(13) . . ?
C3 Ru1 C6 78.21(14) . . ?
C4 Ru1 C6 66.09(13) . . ?
C2 Ru1 C6 66.17(15) . . ?
C5 Ru1 C6 37.34(13) . . ?
C7 Ru1 C6 35.39(15) . . ?
N1 Ru1 P1 86.60(9) . . ?
C3 Ru1 P1 91.81(10) . . ?
C4 Ru1 P1 93.36(10) . . ?
C2 Ru1 P1 116.92(10) . . ?
C5 Ru1 P1 119.77(9) . . ?
C7 Ru1 P1 154.24(11) . . ?
C6 Ru1 P1 157.09(10) . . ?
N1 Ru1 Cl1 87.29(10) . . ?
C3 Ru1 Cl1 152.29(11) . . ?
C4 Ru1 Cl1 114.72(11) . . ?
C2 Ru1 Cl1 158.62(10) . . ?
C5 Ru1 Cl1 90.35(11) . . ?
C7 Ru1 Cl1 121.27(11) . . ?
C6 Ru1 Cl1 94.85(11) . . ?
P1 Ru1 Cl1 84.41(3) . . ?
O1 P1 C14 99.27(19) . . ?
O1 P1 C15 105.5(2) . . ?
C14 P1 C15 103.8(2) . . ?
O1 P1 Ru1 114.99(11) . . ?
C14 P1 Ru1 116.05(16) . . ?
C15 P1 Ru1 115.28(13) . . ?
C11 N2 C12 118.0(4) . . ?
C11 N2 C13 116.6(4) . . ?
C12 N2 C13 116.5(4) . . ?
C16 O1 P1 119.9(3) . . ?
C7 C6 C5 121.2(3) . . ?
C7 C6 Ru1 71.8(2) . . ?
C5 C6 Ru1 69.8(2) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 Ru1 73.1(2) . . ?
C4 C3 Ru1 71.7(2) . . ?
C11 N1 Ru1 174.8(3) . . ?
C4 C5 C6 117.7(4) . . ?
C4 C5 C8 122.6(3) . . ?
C6 C5 C8 119.6(3) . . ?
C4 C5 Ru1 70.0(2) . . ?
C6 C5 Ru1 72.8(2) . . ?
C8 C5 Ru1 131.0(3) . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 Ru1 72.8(2) . . ?
C2 C7 Ru1 69.9(2) . . ?
N1 C11 N2 176.2(4) . . ?
C3 C2 C7 117.5(4) . . ?
C3 C2 C1 121.9(4) . . ?
C7 C2 C1 120.6(3) . . ?
C3 C2 Ru1 69.5(2) . . ?
C7 C2 Ru1 72.7(2) . . ?
C1 C2 Ru1 130.2(3) . . ?
C5 C4 C3 121.0(3) . . ?
C5 C4 Ru1 73.0(2) . . ?
C3 C4 Ru1 70.4(2) . . ?
C5 C8 C10 114.7(4) . . ?
C5 C8 C9 108.2(4) . . ?
C10 C8 C9 110.2(4) . . ?

_refine_diff_density_max         1.353
_refine_diff_density_min         -0.895
_refine_diff_density_rms         0.105

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1989798'
loop_
_audit_author_name
_audit_author_address
'Victorio Cadierno'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2020-03-11 deposited with the CCDC.	2020-06-01 downloaded from the CCDC.
;
#======================================================================= 

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H31 N2 O1 Cl1 F6 P1 Ru1 Sb1'
_chemical_formula_sum            'C17 H31 Cl F6 N2 O P Ru Sb'
_chemical_formula_weight         682.68

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Sb Sb -0.0562 5.8946 '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                   8.3717(3)
_cell_length_b                   21.5740(6)
_cell_length_c                   14.8558(6)
_cell_angle_alpha                90
_cell_angle_beta                 105.025(4)
_cell_angle_gamma                90
_cell_volume                     2591.39(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6523
_cell_measurement_theta_min      3.6760
_cell_measurement_theta_max      69.3820

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    15.020
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2640
_diffrn_reflns_number            13035
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.700
_diffrn_reflns_theta_max         69.807
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4791
_reflns_number_gt                3983
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0720P)²+16.1734P] 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         4791
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1477
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
Sb1 Sb 0.33452(8) 0.86913(3) 0.15200(5) 0.0629(2) Uani 1 1 d . . . . .
Ru1 Ru 0.97568(7) 0.61086(2) 0.14035(4) 0.03778(19) Uani 1 1 d . . . . .
Cl1 Cl 0.7617(3) 0.59776(10) -0.00130(14) 0.0534(5) Uani 1 1 d . . . . .
O1 O 0.8796(7) 0.7145(3) 0.2698(4) 0.0523(14) Uani 1 1 d . . . . .
N1 N 0.8402(9) 0.5521(3) 0.2012(5) 0.0502(16) Uani 1 1 d . . . . .
F6 F 0.1209(10) 0.8461(5) 0.1474(7) 0.132(3) Uani 1 1 d . . . . .
F4 F 0.4051(13) 0.8066(4) 0.2423(9) 0.165(5) Uani 1 1 d . . . . .
C4 C 1.1800(10) 0.6756(4) 0.1794(6) 0.0503(19) Uani 1 1 d . . . . .
H4 H 1.1743 0.7181 0.1952 0.060 Uiso 1 1 calc R U . . .
C14 C 0.7935(11) 0.7537(4) 0.0902(7) 0.057(2) Uani 1 1 d . . . . .
H14A H 0.7269 0.7864 0.1084 0.086 Uiso 1 1 calc R U . . .
H14B H 0.7420 0.7409 0.0259 0.086 Uiso 1 1 calc R U . . .
H14C H 0.9051 0.7694 0.0946 0.086 Uiso 1 1 calc R U . . .
C13 C 0.6865(16) 0.4894(6) 0.3718(8) 0.083(3) Uani 1 1 d . . . . .
H13A H 0.7329 0.4486 0.3925 0.125 Uiso 1 1 calc R U . . .
H13B H 0.5844 0.4955 0.3913 0.125 Uiso 1 1 calc R U . . .
H13C H 0.7666 0.5216 0.3997 0.125 Uiso 1 1 calc R U . . .
C3 C 1.1616(10) 0.6592(4) 0.0860(6) 0.0496(19) Uani 1 1 d . . . . .
H3 H 1.1431 0.6905 0.0394 0.060 Uiso 1 1 calc R U . . .
C6 C 1.2082(10) 0.5673(4) 0.2227(6) 0.051(2) Uani 1 1 d . . . . .
H6 H 1.2207 0.5354 0.2680 0.061 Uiso 1 1 calc R U . . .
N2 N 0.6501(10) 0.4932(4) 0.2701(5) 0.0577(18) Uani 1 1 d . . . . .
C5 C 1.2072(9) 0.6297(4) 0.2516(6) 0.0477(19) Uani 1 1 d . . . . .
F5 F 0.320(2) 0.8099(7) 0.0613(11) 0.237(8) Uani 1 1 d . . . . .
C11 C 0.7547(10) 0.5236(4) 0.2341(6) 0.0471(18) Uani 1 1 d . . . . .
C16 C 0.8020(11) 0.7618(5) 0.3109(8) 0.075(3) Uani 1 1 d . . . . .
H16A H 0.6971 0.7460 0.3212 0.091 Uiso 1 1 calc R U . . .
H16B H 0.7758 0.7978 0.2683 0.091 Uiso 1 1 calc R U . . .
C17 C 0.9127(15) 0.7814(6) 0.4003(8) 0.083(3) Uani 1 1 d . . . . .
H17A H 0.9440 0.7452 0.4409 0.125 Uiso 1 1 calc R U . . .
H17B H 0.8556 0.8115 0.4303 0.125 Uiso 1 1 calc R U . . .
H17C H 1.0122 0.8004 0.3893 0.125 Uiso 1 1 calc R U . . .
C2 C 1.1706(10) 0.5957(4) 0.0602(6) 0.053(2) Uani 1 1 d . . . . .
C7 C 1.1911(10) 0.5507(4) 0.1271(6) 0.051(2) Uani 1 1 d . . . . .
H7 H 1.1940 0.5083 0.1102 0.062 Uiso 1 1 calc R U . . .
C1 C 1.1446(14) 0.5787(5) -0.0416(7) 0.073(3) Uani 1 1 d . . . . .
H1A H 1.0970 0.5370 -0.0524 0.109 Uiso 1 1 calc R U . . .
H1B H 1.2510 0.5795 -0.0576 0.109 Uiso 1 1 calc R U . . .
H1C H 1.0690 0.6085 -0.0806 0.109 Uiso 1 1 calc R U . . .
F2 F 0.259(2) 0.9295(5) 0.0691(9) 0.215(7) Uani 1 1 d . . . . .
C8 C 1.2358(11) 0.6475(5) 0.3519(6) 0.061(2) Uani 1 1 d . . . . .
H8 H 1.1878 0.6899 0.3532 0.074 Uiso 1 1 calc R U . . .
C10 C 1.156(2) 0.6067(6) 0.4072(8) 0.114(6) Uani 1 1 d . . . . .
H10A H 1.0379 0.6028 0.3759 0.171 Uiso 1 1 calc R U . . .
H10B H 1.1690 0.6245 0.4693 0.171 Uiso 1 1 calc R U . . .
H10C H 1.2077 0.5656 0.4129 0.171 Uiso 1 1 calc R U . . .
C12 C 0.5633(14) 0.4413(6) 0.2174(9) 0.084(3) Uani 1 1 d . . . . .
H12A H 0.5287 0.4523 0.1512 0.126 Uiso 1 1 calc R U . . .
H12B H 0.4657 0.4314 0.2395 0.126 Uiso 1 1 calc R U . . .
H12C H 0.6369 0.4053 0.2259 0.126 Uiso 1 1 calc R U . . .
C15 C 0.5934(11) 0.6685(4) 0.1598(7) 0.059(2) Uani 1 1 d . . . . .
H15A H 0.5897 0.6392 0.2096 0.088 Uiso 1 1 calc R U . . .
H15B H 0.5431 0.6495 0.0991 0.088 Uiso 1 1 calc R U . . .
H15C H 0.5321 0.7062 0.1668 0.088 Uiso 1 1 calc R U . . .
F1 F 0.5499(14) 0.8852(7) 0.1609(13) 0.207(7) Uani 1 1 d . . . . .
P1 P 0.8056(2) 0.68830(9) 0.16665(14) 0.0428(4) Uani 1 1 d . . . . .
C9 C 1.4226(16) 0.6534(11) 0.3914(10) 0.142(8) Uani 1 1 d . . . . .
H9A H 1.4472 0.6640 0.4577 0.213 Uiso 1 1 calc R U . . .
H9B H 1.4648 0.6861 0.3580 0.213 Uiso 1 1 calc R U . . .
H9C H 1.4757 0.6140 0.3838 0.213 Uiso 1 1 calc R U . . .
F3 F 0.3372(13) 0.9235(4) 0.2471(6) 0.124(3) 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
Sb1 F2 1.792(9) . ?
Sb1 F1 1.807(10) . ?
Sb1 F3 1.832(8) . ?
Sb1 F5 1.837(10) . ?
Sb1 F6 1.840(8) . ?
Sb1 F4 1.886(10) . ?
Ru1 N1 2.060(7) . ?
Ru1 C4 2.168(7) . ?
Ru1 C3 2.195(7) . ?
Ru1 C6 2.221(7) . ?
Ru1 C5 2.234(7) . ?
Ru1 C7 2.271(8) . ?
Ru1 C2 2.279(8) . ?
Ru1 P1 2.293(2) . ?
Ru1 Cl1 2.4004(19) . ?
O1 C16 1.430(11) . ?
O1 P1 1.600(6) . ?
N1 C11 1.144(10) . ?
C4 C3 1.401(12) . ?
C4 C5 1.434(12) . ?
C14 P1 1.797(9) . ?
C13 N2 1.464(13) . ?
C3 C2 1.430(13) . ?
C6 C5 1.414(11) . ?
C6 C7 1.436(13) . ?
N2 C11 1.314(10) . ?
N2 C12 1.448(13) . ?
C5 C8 1.496(12) . ?
C16 C17 1.470(14) . ?
C2 C7 1.368(13) . ?
C2 C1 1.516(13) . ?
C8 C10 1.478(18) . ?
C8 C9 1.527(16) . ?
C15 P1 1.804(9) . ?

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
F2 Sb1 F1 94.6(7) . . ?
F2 Sb1 F3 89.7(6) . . ?
F1 Sb1 F3 90.5(6) . . ?
F2 Sb1 F5 93.3(8) . . ?
F1 Sb1 F5 93.6(8) . . ?
F3 Sb1 F5 174.7(7) . . ?
F2 Sb1 F6 90.1(6) . . ?
F1 Sb1 F6 175.0(6) . . ?
F3 Sb1 F6 91.1(5) . . ?
F5 Sb1 F6 84.6(7) . . ?
F2 Sb1 F4 176.9(7) . . ?
F1 Sb1 F4 87.8(6) . . ?
F3 Sb1 F4 88.3(5) . . ?
F5 Sb1 F4 88.5(7) . . ?
F6 Sb1 F4 87.5(5) . . ?
N1 Ru1 C4 139.9(3) . . ?
N1 Ru1 C3 168.0(3) . . ?
C4 Ru1 C3 37.5(3) . . ?
N1 Ru1 C6 90.1(3) . . ?
C4 Ru1 C6 66.9(3) . . ?
C3 Ru1 C6 78.5(3) . . ?
N1 Ru1 C5 105.0(3) . . ?
C4 Ru1 C5 38.0(3) . . ?
C3 Ru1 C5 67.9(3) . . ?
C6 Ru1 C5 37.0(3) . . ?
N1 Ru1 C7 103.1(3) . . ?
C4 Ru1 C7 78.6(3) . . ?
C3 Ru1 C7 65.5(3) . . ?
C6 Ru1 C7 37.3(3) . . ?
C5 Ru1 C7 67.2(3) . . ?
N1 Ru1 C2 133.7(3) . . ?
C4 Ru1 C2 67.0(3) . . ?
C3 Ru1 C2 37.2(3) . . ?
C6 Ru1 C2 65.4(3) . . ?
C5 Ru1 C2 79.1(3) . . ?
C7 Ru1 C2 35.0(3) . . ?
N1 Ru1 P1 86.4(2) . . ?
C4 Ru1 P1 88.1(2) . . ?
C3 Ru1 P1 104.3(2) . . ?
C6 Ru1 P1 135.1(2) . . ?
C5 Ru1 P1 101.5(2) . . ?
C7 Ru1 P1 166.6(2) . . ?
C2 Ru1 P1 138.9(3) . . ?
N1 Ru1 Cl1 86.7(2) . . ?
C4 Ru1 Cl1 131.9(2) . . ?
C3 Ru1 Cl1 99.9(2) . . ?
C6 Ru1 Cl1 141.4(2) . . ?
C5 Ru1 Cl1 167.7(2) . . ?
C7 Ru1 Cl1 106.6(2) . . ?
C2 Ru1 Cl1 89.9(2) . . ?
P1 Ru1 Cl1 83.11(7) . . ?
C16 O1 P1 123.8(5) . . ?
C11 N1 Ru1 173.8(7) . . ?
C3 C4 C5 121.5(7) . . ?
C3 C4 Ru1 72.3(4) . . ?
C5 C4 Ru1 73.5(4) . . ?
C4 C3 C2 120.5(8) . . ?
C4 C3 Ru1 70.2(4) . . ?
C2 C3 Ru1 74.6(4) . . ?
C5 C6 C7 122.1(8) . . ?
C5 C6 Ru1 72.0(4) . . ?
C7 C6 Ru1 73.3(5) . . ?
C11 N2 C12 117.4(8) . . ?
C11 N2 C13 117.7(9) . . ?
C12 N2 C13 117.1(9) . . ?
C6 C5 C4 116.3(8) . . ?
C6 C5 C8 122.3(8) . . ?
C4 C5 C8 121.4(8) . . ?
C6 C5 Ru1 71.0(4) . . ?
C4 C5 Ru1 68.5(4) . . ?
C8 C5 Ru1 131.9(6) . . ?
N1 C11 N2 176.9(9) . . ?
O1 C16 C17 109.9(8) . . ?
C7 C2 C3 119.4(8) . . ?
C7 C2 C1 120.7(9) . . ?
C3 C2 C1 119.7(9) . . ?
C7 C2 Ru1 72.2(5) . . ?
C3 C2 Ru1 68.2(4) . . ?
C1 C2 Ru1 128.2(6) . . ?
C2 C7 C6 120.1(8) . . ?
C2 C7 Ru1 72.8(5) . . ?
C6 C7 Ru1 69.5(4) . . ?
C10 C8 C5 114.9(9) . . ?
C10 C8 C9 113.7(12) . . ?
C5 C8 C9 106.7(9) . . ?
O1 P1 C14 105.8(4) . . ?
O1 P1 C15 105.6(4) . . ?
C14 P1 C15 104.8(4) . . ?
O1 P1 Ru1 108.5(2) . . ?
C14 P1 Ru1 113.6(3) . . ?
C15 P1 Ru1 117.6(3) . . ?

_refine_diff_density_max         2.278
_refine_diff_density_min         -1.437
_refine_diff_density_rms         0.147

_shelxl_version_number           2014-3

