# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_6c
_database_code_depnum_ccdc_archive 'CCDC 1958494'
loop_
_audit_author_name
_audit_author_address
'Victorio Cadierno'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2019-10-10 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;
#======================================================================= 

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H39 O1 Cl2 P1 Ru'
_chemical_formula_sum            'C25 H39 Cl2 O P Ru'
_chemical_formula_weight         558.50

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'
O O 0.0492 0.0322 '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'

_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                   9.36960(10)
_cell_length_b                   15.1236(2)
_cell_length_c                   18.3093(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.7960(10)
_cell_angle_gamma                90
_cell_volume                     2563.95(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9101
_cell_measurement_theta_min      3.7980
_cell_measurement_theta_max      69.4750

_exptl_crystal_description       blocks
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_F_000             1160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    7.557
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.69361
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            14073
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.809
_diffrn_reflns_theta_max         69.591
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4781
_reflns_number_gt                4330
_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)+(0.0267P)²+0.0925P] 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         4781
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0216
_refine_ls_wR_factor_ref         0.0528
_refine_ls_wR_factor_gt          0.0508
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
C1 C 0.3556(2) 0.25428(17) 0.59605(13) 0.0372(5) Uani 1 1 d . . . . .
H1A H 0.3813 0.2031 0.6282 0.056 Uiso 1 1 calc R U . . .
H1B H 0.2788 0.2377 0.5559 0.056 Uiso 1 1 calc R U . . .
H1C H 0.3217 0.3024 0.6249 0.056 Uiso 1 1 calc R U . . .
C2 C 0.4859(2) 0.28443(14) 0.56419(10) 0.0266(4) Uani 1 1 d . . . . .
C3 C 0.6197(2) 0.24062(13) 0.57848(10) 0.0246(4) Uani 1 1 d . . . . .
H3 H 0.6292 0.1894 0.6089 0.030 Uiso 1 1 calc R U . . .
C4 C 0.7409(2) 0.27198(13) 0.54804(10) 0.0234(4) Uani 1 1 d . . . . .
H4 H 0.8299 0.2409 0.5579 0.028 Uiso 1 1 calc R U . . .
C5 C 0.7314(2) 0.34851(14) 0.50347(10) 0.0231(4) Uani 1 1 d . . . . .
C6 C 0.5925(2) 0.39079(14) 0.48697(10) 0.0249(4) Uani 1 1 d . . . . .
H6 H 0.5818 0.4410 0.4554 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4747(2) 0.35977(14) 0.51617(10) 0.0263(4) Uani 1 1 d . . . . .
H7 H 0.3843 0.3889 0.5042 0.032 Uiso 1 1 calc R U . . .
C8 C 0.8580(2) 0.38491(15) 0.47047(10) 0.0278(4) Uani 1 1 d . . . . .
H8 H 0.8703 0.4484 0.4853 0.033 Uiso 1 1 calc R U . . .
C9 C 0.8222(3) 0.38131(16) 0.38586(11) 0.0358(5) Uani 1 1 d . . . . .
H9A H 0.8051 0.3198 0.3700 0.054 Uiso 1 1 calc R U . . .
H9B H 0.9033 0.4053 0.3641 0.054 Uiso 1 1 calc R U . . .
H9C H 0.7353 0.4165 0.3694 0.054 Uiso 1 1 calc R U . . .
C10 C 0.9994(2) 0.33794(19) 0.49648(13) 0.0404(6) Uani 1 1 d . . . . .
H10A H 1.0211 0.3408 0.5505 0.061 Uiso 1 1 calc R U . . .
H10B H 1.0770 0.3667 0.4750 0.061 Uiso 1 1 calc R U . . .
H10C H 0.9915 0.2760 0.4807 0.061 Uiso 1 1 calc R U . . .
C11 C 0.9616(2) 0.39748(14) 0.76084(11) 0.0285(4) Uani 1 1 d . . . . .
H11 H 1.0114 0.3623 0.8035 0.034 Uiso 1 1 calc R U . . .
C12 C 1.0692(2) 0.40722(17) 0.70637(13) 0.0370(5) Uani 1 1 d . . . . .
H12A H 1.0233 0.4390 0.6623 0.056 Uiso 1 1 calc R U . . .
H12B H 1.0995 0.3485 0.6921 0.056 Uiso 1 1 calc R U . . .
H12C H 1.1538 0.4404 0.7298 0.056 Uiso 1 1 calc R U . . .
C13 C 0.9201(3) 0.48597(15) 0.79239(12) 0.0394(5) Uani 1 1 d . . . . .
H13A H 1.0078 0.5183 0.8128 0.059 Uiso 1 1 calc R U . . .
H13B H 0.8618 0.4752 0.8316 0.059 Uiso 1 1 calc R U . . .
H13C H 0.8641 0.5210 0.7530 0.059 Uiso 1 1 calc R U . . .
C14 C 0.7047(2) 0.31401(15) 0.79932(10) 0.0289(4) Uani 1 1 d . . . . .
H14 H 0.6565 0.3711 0.8082 0.035 Uiso 1 1 calc R U . . .
C15 C 0.5849(3) 0.24649(17) 0.77923(13) 0.0402(5) Uani 1 1 d . . . . .
H15A H 0.6271 0.1896 0.7682 0.060 Uiso 1 1 calc R U . . .
H15B H 0.5191 0.2670 0.7357 0.060 Uiso 1 1 calc R U . . .
H15C H 0.5314 0.2393 0.8208 0.060 Uiso 1 1 calc R U . . .
C16 C 0.7974(3) 0.28834(17) 0.87270(11) 0.0390(5) Uani 1 1 d . . . . .
H16A H 0.7374 0.2884 0.9121 0.058 Uiso 1 1 calc R U . . .
H16B H 0.8761 0.3311 0.8846 0.058 Uiso 1 1 calc R U . . .
H16C H 0.8378 0.2292 0.8683 0.058 Uiso 1 1 calc R U . . .
C17 C 0.9669(2) 0.18224(14) 0.74994(10) 0.0296(4) Uani 1 1 d . . . . .
H17A H 0.9115 0.1388 0.7748 0.036 Uiso 1 1 calc R U . . .
H17B H 1.0254 0.2186 0.7883 0.036 Uiso 1 1 calc R U . . .
C18 C 1.0642(2) 0.13474(14) 0.70403(11) 0.0287(4) Uani 1 1 d . . . . .
H18A H 1.1373 0.1008 0.7375 0.034 Uiso 1 1 calc R U . . .
H18B H 1.1161 0.1793 0.6785 0.034 Uiso 1 1 calc R U . . .
C19 C 0.9850(2) 0.07172(14) 0.64649(11) 0.0294(4) Uani 1 1 d . . . . .
H19A H 0.9289 0.0286 0.6713 0.035 Uiso 1 1 calc R U . . .
H19B H 0.9162 0.1057 0.6107 0.035 Uiso 1 1 calc R U . . .
C20 C 1.0889(2) 0.02269(14) 0.60566(10) 0.0270(4) Uani 1 1 d . . . . .
C21 C 1.1429(3) 0.06194(16) 0.54718(11) 0.0356(5) Uani 1 1 d . . . . .
H21 H 1.1086 0.1186 0.5304 0.043 Uiso 1 1 calc R U . . .
C22 C 1.2454(3) 0.02008(18) 0.51291(13) 0.0457(6) Uani 1 1 d . . . . .
H22 H 1.2827 0.0487 0.4737 0.055 Uiso 1 1 calc R U . . .
C23 C 1.2942(3) -0.06319(18) 0.53539(13) 0.0451(6) Uani 1 1 d . . . . .
H23 H 1.3656 -0.0918 0.5121 0.054 Uiso 1 1 calc R U . . .
C24 C 1.2382(3) -0.10448(17) 0.59182(13) 0.0390(5) Uani 1 1 d . . . . .
H24 H 1.2688 -0.1626 0.6064 0.047 Uiso 1 1 calc R U . . .
C25 C 1.1373(2) -0.06156(15) 0.62752(12) 0.0318(5) Uani 1 1 d . . . . .
H25 H 1.1011 -0.0900 0.6672 0.038 Uiso 1 1 calc R U . . .
O1 O 0.86873(14) 0.23823(9) 0.70117(7) 0.0267(3) Uani 1 1 d . . . . .
P1 P 0.80270(5) 0.33288(3) 0.72037(2) 0.02098(10) Uani 1 1 d . . . . .
Cl1 Cl 0.49233(5) 0.44706(3) 0.68181(2) 0.02902(11) Uani 1 1 d . . . . .
Cl2 Cl 0.77121(5) 0.52125(3) 0.61191(2) 0.02844(11) Uani 1 1 d . . . . .
Ru1 Ru 0.65727(2) 0.37829(2) 0.61067(2) 0.01831(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.502(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.407(3) . ?
C2 C7 1.433(3) . ?
C2 Ru1 2.2135(19) . ?
C3 C4 1.421(3) . ?
C3 Ru1 2.1778(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(3) . ?
C4 Ru1 2.1885(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.439(3) . ?
C5 C8 1.515(3) . ?
C5 Ru1 2.2258(17) . ?
C6 C7 1.381(3) . ?
C6 Ru1 2.2612(18) . ?
C6 H6 0.9500 . ?
C7 Ru1 2.2570(18) . ?
C7 H7 0.9500 . ?
C8 C10 1.515(3) . ?
C8 C9 1.535(3) . ?
C8 H8 1.0000 . ?
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 1.530(3) . ?
C11 C13 1.531(3) . ?
C11 P1 1.839(2) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.520(3) . ?
C14 C16 1.534(3) . ?
C14 P1 1.8495(19) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 O1 1.452(2) . ?
C17 C18 1.513(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.527(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.509(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.386(3) . ?
C20 C25 1.391(3) . ?
C21 C22 1.379(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.377(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
O1 P1 1.6193(14) . ?
P1 Ru1 2.3506(5) . ?
Cl1 Ru1 2.4045(4) . ?
Cl2 Ru1 2.4098(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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 117.92(18) . . ?
C3 C2 C1 122.6(2) . . ?
C7 C2 C1 119.46(19) . . ?
C3 C2 Ru1 69.94(11) . . ?
C7 C2 Ru1 72.96(11) . . ?
C1 C2 Ru1 129.06(14) . . ?
C2 C3 C4 120.86(18) . . ?
C2 C3 Ru1 72.70(11) . . ?
C4 C3 Ru1 71.42(11) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
Ru1 C3 H3 128.6 . . ?
C5 C4 C3 121.10(17) . . ?
C5 C4 Ru1 72.80(11) . . ?
C3 C4 Ru1 70.60(11) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
Ru1 C4 H4 129.7 . . ?
C4 C5 C6 117.47(17) . . ?
C4 C5 C8 122.98(17) . . ?
C6 C5 C8 119.50(18) . . ?
C4 C5 Ru1 69.93(10) . . ?
C6 C5 Ru1 72.63(10) . . ?
C8 C5 Ru1 130.32(14) . . ?
C7 C6 C5 121.23(18) . . ?
C7 C6 Ru1 72.04(11) . . ?
C5 C6 Ru1 69.96(10) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
Ru1 C6 H6 131.6 . . ?
C6 C7 C2 121.31(18) . . ?
C6 C7 Ru1 72.38(10) . . ?
C2 C7 Ru1 69.66(10) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
Ru1 C7 H7 131.6 . . ?
C10 C8 C5 113.88(17) . . ?
C10 C8 C9 110.26(17) . . ?
C5 C8 C9 109.03(17) . . ?
C10 C8 H8 107.8 . . ?
C5 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 113.11(19) . . ?
C12 C11 P1 111.23(15) . . ?
C13 C11 P1 112.32(15) . . ?
C12 C11 H11 106.6 . . ?
C13 C11 H11 106.6 . . ?
P1 C11 H11 106.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C16 109.88(18) . . ?
C15 C14 P1 110.54(14) . . ?
C16 C14 P1 116.19(15) . . ?
C15 C14 H14 106.6 . . ?
C16 C14 H14 106.6 . . ?
P1 C14 H14 106.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 C18 108.30(15) . . ?
O1 C17 H17A 110.0 . . ?
C18 C17 H17A 110.0 . . ?
O1 C17 H17B 110.0 . . ?
C18 C17 H17B 110.0 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 C19 114.14(17) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 111.48(16) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 108.0 . . ?
C21 C20 C25 118.2(2) . . ?
C21 C20 C19 120.8(2) . . ?
C25 C20 C19 120.95(19) . . ?
C22 C21 C20 121.1(2) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C24 C23 C22 119.4(2) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C25 120.3(2) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C24 C25 C20 120.5(2) . . ?
C24 C25 H25 119.7 . . ?
C20 C25 H25 119.7 . . ?
C17 O1 P1 127.51(12) . . ?
O1 P1 C11 104.15(9) . . ?
O1 P1 C14 106.57(9) . . ?
C11 P1 C14 103.60(9) . . ?
O1 P1 Ru1 105.28(5) . . ?
C11 P1 Ru1 121.12(7) . . ?
C14 P1 Ru1 114.88(7) . . ?
C3 Ru1 C4 37.98(7) . . ?
C3 Ru1 C2 37.36(8) . . ?
C4 Ru1 C2 67.93(7) . . ?
C3 Ru1 C5 68.11(7) . . ?
C4 Ru1 C5 37.27(7) . . ?
C2 Ru1 C5 80.61(7) . . ?
C3 Ru1 C7 66.53(7) . . ?
C4 Ru1 C7 78.31(7) . . ?
C2 Ru1 C7 37.38(8) . . ?
C5 Ru1 C7 66.48(7) . . ?
C3 Ru1 C6 78.54(7) . . ?
C4 Ru1 C6 66.38(7) . . ?
C2 Ru1 C6 66.47(7) . . ?
C5 Ru1 C6 37.41(7) . . ?
C7 Ru1 C6 35.58(7) . . ?
C3 Ru1 P1 90.03(5) . . ?
C4 Ru1 P1 91.48(5) . . ?
C2 Ru1 P1 115.65(6) . . ?
C5 Ru1 P1 118.43(5) . . ?
C7 Ru1 P1 153.02(6) . . ?
C6 Ru1 P1 155.77(5) . . ?
C3 Ru1 Cl1 118.00(5) . . ?
C4 Ru1 Cl1 155.92(5) . . ?
C2 Ru1 Cl1 89.84(5) . . ?
C5 Ru1 Cl1 151.42(5) . . ?
C7 Ru1 Cl1 89.67(5) . . ?
C6 Ru1 Cl1 114.22(5) . . ?
P1 Ru1 Cl1 90.010(16) . . ?
C3 Ru1 Cl2 155.96(5) . . ?
C4 Ru1 Cl2 118.06(5) . . ?
C2 Ru1 Cl2 150.84(6) . . ?
C5 Ru1 Cl2 89.56(5) . . ?
C7 Ru1 Cl2 113.66(6) . . ?
C6 Ru1 Cl2 89.14(5) . . ?
P1 Ru1 Cl2 93.211(16) . . ?
Cl1 Ru1 Cl2 85.835(18) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 2.0(3) . . . . ?
C1 C2 C3 C4 -179.15(18) . . . . ?
Ru1 C2 C3 C4 -54.90(16) . . . . ?
C7 C2 C3 Ru1 56.87(15) . . . . ?
C1 C2 C3 Ru1 -124.25(18) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
Ru1 C3 C4 C5 -54.64(16) . . . . ?
C2 C3 C4 Ru1 55.50(16) . . . . ?
C3 C4 C5 C6 -3.1(3) . . . . ?
Ru1 C4 C5 C6 -56.76(15) . . . . ?
C3 C4 C5 C8 179.39(17) . . . . ?
Ru1 C4 C5 C8 125.75(18) . . . . ?
C3 C4 C5 Ru1 53.64(16) . . . . ?
C4 C5 C6 C7 2.6(3) . . . . ?
C8 C5 C6 C7 -179.79(18) . . . . ?
Ru1 C5 C6 C7 -52.77(16) . . . . ?
C4 C5 C6 Ru1 55.40(14) . . . . ?
C8 C5 C6 Ru1 -127.02(17) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
Ru1 C6 C7 C2 -51.68(16) . . . . ?
C5 C6 C7 Ru1 51.84(16) . . . . ?
C3 C2 C7 C6 -2.5(3) . . . . ?
C1 C2 C7 C6 178.61(18) . . . . ?
Ru1 C2 C7 C6 52.89(17) . . . . ?
C3 C2 C7 Ru1 -55.36(15) . . . . ?
C1 C2 C7 Ru1 125.72(18) . . . . ?
C4 C5 C8 C10 -6.5(3) . . . . ?
C6 C5 C8 C10 176.10(18) . . . . ?
Ru1 C5 C8 C10 84.4(2) . . . . ?
C4 C5 C8 C9 117.1(2) . . . . ?
C6 C5 C8 C9 -60.3(2) . . . . ?
Ru1 C5 C8 C9 -152.04(16) . . . . ?
O1 C17 C18 C19 -63.7(2) . . . . ?
C17 C18 C19 C20 -176.75(17) . . . . ?
C18 C19 C20 C21 -81.5(2) . . . . ?
C18 C19 C20 C25 95.9(2) . . . . ?
C25 C20 C21 C22 -2.1(3) . . . . ?
C19 C20 C21 C22 175.4(2) . . . . ?
C20 C21 C22 C23 1.5(4) . . . . ?
C21 C22 C23 C24 0.7(4) . . . . ?
C22 C23 C24 C25 -2.2(3) . . . . ?
C23 C24 C25 C20 1.5(3) . . . . ?
C21 C20 C25 C24 0.6(3) . . . . ?
C19 C20 C25 C24 -176.89(18) . . . . ?
C18 C17 O1 P1 -147.05(15) . . . . ?
C17 O1 P1 C11 50.98(17) . . . . ?
C17 O1 P1 C14 -58.17(18) . . . . ?
C17 O1 P1 Ru1 179.40(14) . . . . ?
C12 C11 P1 O1 59.64(16) . . . . ?
C13 C11 P1 O1 -172.43(14) . . . . ?
C12 C11 P1 C14 170.96(15) . . . . ?
C13 C11 P1 C14 -61.11(16) . . . . ?
C12 C11 P1 Ru1 -58.38(17) . . . . ?
C13 C11 P1 Ru1 69.55(16) . . . . ?
C15 C14 P1 O1 -59.61(17) . . . . ?
C16 C14 P1 O1 66.47(18) . . . . ?
C15 C14 P1 C11 -169.15(16) . . . . ?
C16 C14 P1 C11 -43.06(19) . . . . ?
C15 C14 P1 Ru1 56.56(17) . . . . ?
C16 C14 P1 Ru1 -177.35(15) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.057

_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_10b
_database_code_depnum_ccdc_archive 'CCDC 1958496'
loop_
_audit_author_name
_audit_author_address
'Victorio Cadierno'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2019-10-10 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;
#======================================================================= 

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H23 Cl2 O1 P1 Ru1'
_chemical_formula_sum            'C14 H23 Cl2 O P Ru'
_chemical_formula_weight         410.26

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'
O O 0.0492 0.0322 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   8.81080(10)
_cell_length_b                   13.2483(2)
_cell_length_c                   27.2268(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3178.13(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6162
_cell_measurement_theta_min      3.7080
_cell_measurement_theta_max      69.4140

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_F_000             1664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    11.941
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            10246
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.246
_diffrn_reflns_theta_max         69.557
_diffrn_reflns_theta_full        68.1328
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2953
_reflns_number_gt                2696
_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)+(0.0368P)²+1.6152P] 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         2953
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0262
_refine_ls_wR_factor_ref         0.0673
_refine_ls_wR_factor_gt          0.0648
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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
C5 C 0.0173(3) 0.0385(2) 0.08103(11) 0.0299(6) Uani 1 1 d . . . . .
H5 H -0.0019 -0.0015 0.1093 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1656(4) 0.0468(3) 0.06262(14) 0.0401(8) Uani 1 1 d . . . . .
H6 H 0.2473 0.0167 0.0800 0.048 Uiso 1 1 calc R U . . .
C1 C 0.1944(4) 0.0992(3) 0.01850(13) 0.0441(9) Uani 1 1 d . . . . .
H1 H 0.2936 0.1001 0.0049 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0762(4) 0.1496(3) -0.00487(11) 0.0372(8) Uani 1 1 d . . . . .
H2 H 0.0952 0.1852 -0.0345 0.045 Uiso 1 1 calc R U . . .
C3 C -0.0729(3) 0.1482(2) 0.01523(10) 0.0262(6) Uani 1 1 d . . . . .
H3 H -0.1513 0.1865 0.0002 0.031 Uiso 1 1 calc R U . . .
C4 C -0.1047(3) 0.0902(2) 0.05736(10) 0.0241(6) Uani 1 1 d . . . . .
C7 C -0.2625(3) 0.0870(3) 0.07848(11) 0.0325(7) Uani 1 1 d . . . . .
H7A H -0.2778 0.0209 0.0947 0.039 Uiso 1 1 calc R U . . .
H7B H -0.3366 0.0919 0.0513 0.039 Uiso 1 1 calc R U . . .
C8 C -0.2952(3) 0.1699(3) 0.11522(10) 0.0281(6) Uani 1 1 d . . . . .
H8A H -0.2879 0.2362 0.0986 0.034 Uiso 1 1 calc R U . . .
H8B H -0.4001 0.1622 0.1277 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0915(3) 0.3645(2) 0.15856(11) 0.0246(6) Uani 1 1 d . . . . .
H9 H -0.1173 0.3904 0.1251 0.030 Uiso 1 1 calc R U . . .
C10 C 0.0436(3) 0.4283(2) 0.17562(12) 0.0338(7) Uani 1 1 d . . . . .
H10A H 0.0631 0.4153 0.2105 0.051 Uiso 1 1 calc R U . . .
H10B H 0.0205 0.5000 0.1709 0.051 Uiso 1 1 calc R U . . .
H10C H 0.1336 0.4103 0.1564 0.051 Uiso 1 1 calc R U . . .
C11 C -0.2345(3) 0.3822(3) 0.18967(12) 0.0344(7) Uani 1 1 d . . . . .
H11A H -0.2148 0.3618 0.2237 0.052 Uiso 1 1 calc R U . . .
H11B H -0.3185 0.3422 0.1764 0.052 Uiso 1 1 calc R U . . .
H11C H -0.2615 0.4540 0.1888 0.052 Uiso 1 1 calc R U . . .
C12 C 0.0687(3) 0.1909(2) 0.20437(11) 0.0237(6) Uani 1 1 d . . . . .
H12 H 0.1628 0.2329 0.2064 0.028 Uiso 1 1 calc R U . . .
C13 C 0.1195(3) 0.0812(2) 0.19982(12) 0.0328(7) Uani 1 1 d . . . . .
H13A H 0.1774 0.0620 0.2291 0.049 Uiso 1 1 calc R U . . .
H13B H 0.1835 0.0735 0.1706 0.049 Uiso 1 1 calc R U . . .
H13C H 0.0301 0.0375 0.1968 0.049 Uiso 1 1 calc R U . . .
C14 C -0.0178(4) 0.2068(3) 0.25233(11) 0.0342(7) Uani 1 1 d . . . . .
H14A H -0.1151 0.1712 0.2508 0.051 Uiso 1 1 calc R U . . .
H14B H -0.0359 0.2791 0.2573 0.051 Uiso 1 1 calc R U . . .
H14C H 0.0423 0.1804 0.2798 0.051 Uiso 1 1 calc R U . . .
O1 O -0.19054(18) 0.16737(15) 0.15598(6) 0.0212(4) Uani 1 1 d . . . . .
Cl1 Cl 0.04759(7) 0.37093(5) 0.04744(2) 0.02306(14) Uani 1 1 d . . . . .
Cl2 Cl 0.31618(7) 0.25125(6) 0.11102(2) 0.02848(16) Uani 1 1 d . . . . .
Ru1 Ru 0.07812(2) 0.19875(2) 0.07469(2) 0.01779(9) Uani 1 1 d . . . . .
P1 P -0.03448(7) 0.23206(5) 0.14941(2) 0.01713(14) 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
C5 C6 1.403(5) . ?
C5 C4 1.428(4) . ?
C5 Ru1 2.196(3) . ?
C6 C1 1.411(5) . ?
C6 Ru1 2.181(3) . ?
C1 C2 1.391(5) . ?
C1 Ru1 2.264(3) . ?
C2 C3 1.424(4) . ?
C2 Ru1 2.262(3) . ?
C3 C4 1.408(4) . ?
C3 Ru1 2.200(3) . ?
C4 C7 1.506(4) . ?
C4 Ru1 2.210(3) . ?
C7 C8 1.513(4) . ?
C8 O1 1.443(3) . ?
C9 C10 1.532(4) . ?
C9 C11 1.536(4) . ?
C9 P1 1.843(3) . ?
C12 C14 1.526(4) . ?
C12 C13 1.526(4) . ?
C12 P1 1.834(3) . ?
O1 P1 1.6300(18) . ?
Cl1 Ru1 2.4138(7) . ?
Cl2 Ru1 2.4212(6) . ?
Ru1 P1 2.3062(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
C6 C5 C4 120.1(3) . . ?
C6 C5 Ru1 70.71(18) . . ?
C4 C5 Ru1 71.61(16) . . ?
C5 C6 C1 120.7(3) . . ?
C5 C6 Ru1 71.89(17) . . ?
C1 C6 Ru1 74.76(19) . . ?
C2 C1 C6 119.4(3) . . ?
C2 C1 Ru1 72.01(17) . . ?
C6 C1 Ru1 68.29(17) . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 Ru1 72.21(18) . . ?
C3 C2 Ru1 69.05(16) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 Ru1 71.74(15) . . ?
C2 C3 Ru1 73.76(16) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 C7 120.7(3) . . ?
C5 C4 C7 120.6(3) . . ?
C3 C4 Ru1 71.01(15) . . ?
C5 C4 Ru1 70.56(16) . . ?
C7 C4 Ru1 127.6(2) . . ?
C4 C7 C8 114.0(2) . . ?
O1 C8 C7 111.7(2) . . ?
C10 C9 C11 112.7(2) . . ?
C10 C9 P1 110.73(19) . . ?
C11 C9 P1 116.3(2) . . ?
C14 C12 C13 110.3(3) . . ?
C14 C12 P1 114.20(19) . . ?
C13 C12 P1 111.2(2) . . ?
C8 O1 P1 116.26(16) . . ?
C6 Ru1 C5 37.40(13) . . ?
C6 Ru1 C3 79.74(12) . . ?
C5 Ru1 C3 67.43(11) . . ?
C6 Ru1 C4 67.96(11) . . ?
C5 Ru1 C4 37.83(11) . . ?
C3 Ru1 C4 37.25(10) . . ?
C6 Ru1 C2 65.95(14) . . ?
C5 Ru1 C2 78.18(12) . . ?
C3 Ru1 C2 37.18(11) . . ?
C4 Ru1 C2 66.60(10) . . ?
C6 Ru1 C1 36.95(14) . . ?
C5 Ru1 C1 66.46(12) . . ?
C3 Ru1 C1 66.38(12) . . ?
C4 Ru1 C1 78.86(11) . . ?
C2 Ru1 C1 35.78(13) . . ?
C6 Ru1 P1 117.49(10) . . ?
C5 Ru1 P1 90.61(8) . . ?
C3 Ru1 P1 116.56(7) . . ?
C4 Ru1 P1 89.96(7) . . ?
C2 Ru1 P1 153.74(8) . . ?
C1 Ru1 P1 154.42(11) . . ?
C6 Ru1 Cl1 149.96(10) . . ?
C5 Ru1 Cl1 155.57(8) . . ?
C3 Ru1 Cl1 89.66(8) . . ?
C4 Ru1 Cl1 117.91(8) . . ?
C2 Ru1 Cl1 88.68(10) . . ?
C1 Ru1 Cl1 113.14(11) . . ?
P1 Ru1 Cl1 92.43(2) . . ?
C6 Ru1 Cl2 91.19(9) . . ?
C5 Ru1 Cl2 117.18(8) . . ?
C3 Ru1 Cl2 155.81(7) . . ?
C4 Ru1 Cl2 154.89(8) . . ?
C2 Ru1 Cl2 118.71(8) . . ?
C1 Ru1 Cl2 92.95(9) . . ?
P1 Ru1 Cl2 87.55(2) . . ?
Cl1 Ru1 Cl2 87.17(2) . . ?
O1 P1 C12 99.93(11) . . ?
O1 P1 C9 104.83(11) . . ?
C12 P1 C9 107.94(13) . . ?
O1 P1 Ru1 111.04(7) . . ?
C12 P1 Ru1 116.73(9) . . ?
C9 P1 Ru1 114.76(9) . . ?

_refine_diff_density_max         0.575
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.104

_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_10c
_database_code_depnum_ccdc_archive 'CCDC 1958497'
loop_
_audit_author_name
_audit_author_address
'Victorio Cadierno'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2019-10-10 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;
#======================================================================= 

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H25 Ru1 Cl2 O1 P1'
_chemical_formula_sum            'C15 H25 Cl2 O P Ru'
_chemical_formula_weight         424.29

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   8.9634(2)
_cell_length_b                   13.7539(3)
_cell_length_c                   27.5000(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3390.25(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5954
_cell_measurement_theta_min      5.8850
_cell_measurement_theta_max      69.4630

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    11.215
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9404
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.214
_diffrn_reflns_theta_max         69.630
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3147
_reflns_number_gt                2899
_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)+(0.0570P)²+0.2256P] 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         3147
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.000
_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
C1 C 0.1808(4) 0.1329(3) 0.00706(13) 0.0577(9) Uani 1 1 d . . . . .
H1 H 0.2629 0.1523 -0.0112 0.069 Uiso 1 1 calc R U . . .
C2 C 0.0405(4) 0.1650(3) -0.00461(12) 0.0551(8) Uani 1 1 d . . . . .
H2 H 0.0287 0.2068 -0.0309 0.066 Uiso 1 1 calc R U . . .
C3 C -0.0847(3) 0.1368(2) 0.02173(12) 0.0482(7) Uani 1 1 d . . . . .
H3 H -0.1777 0.1613 0.0131 0.058 Uiso 1 1 calc R U . . .
C4 C -0.0741(3) 0.0729(2) 0.06055(14) 0.0465(7) Uani 1 1 d . . . . .
C5 C 0.0713(4) 0.0371(3) 0.07357(13) 0.0564(10) Uani 1 1 d . . . . .
H5 H 0.0823 -0.0070 0.0989 0.068 Uiso 1 1 calc R U . . .
C6 C 0.1991(4) 0.0703(3) 0.04693(16) 0.0615(10) Uani 1 1 d . . . . .
H6 H 0.2942 0.0504 0.0561 0.074 Uiso 1 1 calc R U . . .
C7 C -0.2057(4) 0.0348(3) 0.08866(15) 0.0597(9) Uani 1 1 d . . . . .
H7A H -0.1712 0.0163 0.1208 0.072 Uiso 1 1 calc R U . . .
H7B H -0.2404 -0.0239 0.0727 0.072 Uiso 1 1 calc R U . . .
C8 C -0.3387(3) 0.1028(3) 0.09475(13) 0.0534(8) Uani 1 1 d . . . . .
H8A H -0.3820 0.1154 0.0630 0.064 Uiso 1 1 calc R U . . .
H8B H -0.4138 0.0706 0.1144 0.064 Uiso 1 1 calc R U . . .
C9 C -0.2992(3) 0.1982(2) 0.11816(12) 0.0455(7) Uani 1 1 d . . . . .
H9A H -0.2571 0.2416 0.0940 0.055 Uiso 1 1 calc R U . . .
H9B H -0.3886 0.2283 0.1311 0.055 Uiso 1 1 calc R U . . .
C10 C -0.0644(3) 0.3625(2) 0.16265(12) 0.0428(7) Uani 1 1 d . . . . .
H10 H -0.0938 0.3907 0.1313 0.051 Uiso 1 1 calc R U . . .
C11 C 0.0772(4) 0.4169(3) 0.17750(17) 0.0625(10) Uani 1 1 d . . . . .
H11A H 0.1560 0.4017 0.1551 0.094 Uiso 1 1 calc R U . . .
H11B H 0.0586 0.4856 0.1770 0.094 Uiso 1 1 calc R U . . .
H11C H 0.1060 0.3974 0.2097 0.094 Uiso 1 1 calc R U . . .
C12 C -0.1946(4) 0.3840(3) 0.19727(14) 0.0654(9) Uani 1 1 d . . . . .
H12A H -0.2814 0.3488 0.1869 0.098 Uiso 1 1 calc R U . . .
H12B H -0.1683 0.3643 0.2296 0.098 Uiso 1 1 calc R U . . .
H12C H -0.2157 0.4525 0.1970 0.098 Uiso 1 1 calc R U . . .
C13 C 0.0673(3) 0.1831(3) 0.20365(12) 0.0467(7) Uani 1 1 d . . . . .
H13 H 0.1608 0.2196 0.2068 0.056 Uiso 1 1 calc R U . . .
C14 C -0.0155(5) 0.1960(4) 0.25144(14) 0.0744(12) Uani 1 1 d . . . . .
H14A H -0.0424 0.2631 0.2554 0.112 Uiso 1 1 calc R U . . .
H14B H -0.1041 0.1568 0.2512 0.112 Uiso 1 1 calc R U . . .
H14C H 0.0476 0.1762 0.2779 0.112 Uiso 1 1 calc R U . . .
C15 C 0.1106(5) 0.0776(3) 0.19677(17) 0.0751(11) Uani 1 1 d . . . . .
H15A H 0.1628 0.0703 0.1665 0.113 Uiso 1 1 calc R U . . .
H15B H 0.1741 0.0575 0.2230 0.113 Uiso 1 1 calc R U . . .
H15C H 0.0224 0.0381 0.1964 0.113 Uiso 1 1 calc R U . . .
O1 O -0.1924(2) 0.18373(15) 0.15701(7) 0.0410(4) Uani 1 1 d . . . . .
P1 P -0.02923(7) 0.23261(5) 0.15014(2) 0.03360(17) Uani 1 1 d . . . . .
Cl1 Cl 0.04454(8) 0.36521(5) 0.04908(3) 0.04639(18) Uani 1 1 d . . . . .
Cl2 Cl 0.30933(8) 0.24909(6) 0.11168(3) 0.0553(2) Uani 1 1 d . . . . .
Ru1 Ru 0.07863(2) 0.19812(2) 0.07395(2) 0.03403(11) 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
C1 C2 1.372(6) . ?
C1 C6 1.403(6) . ?
C1 Ru1 2.242(3) . ?
C2 C3 1.391(5) . ?
C2 Ru1 2.234(3) . ?
C3 C4 1.386(5) . ?
C3 Ru1 2.217(3) . ?
C4 C5 1.439(5) . ?
C4 C7 1.505(5) . ?
C4 Ru1 2.230(3) . ?
C5 C6 1.434(5) . ?
C5 Ru1 2.215(4) . ?
C6 Ru1 2.193(3) . ?
C7 C8 1.525(5) . ?
C8 C9 1.504(5) . ?
C9 O1 1.448(4) . ?
C10 C11 1.529(4) . ?
C10 C12 1.535(4) . ?
C10 P1 1.847(3) . ?
C13 C15 1.514(6) . ?
C13 C14 1.520(5) . ?
C13 P1 1.838(3) . ?
O1 P1 1.621(2) . ?
P1 Ru1 2.3557(7) . ?
Cl1 Ru1 2.4170(7) . ?
Cl2 Ru1 2.4175(7) . ?

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
C2 C1 C6 119.2(3) . . ?
C2 C1 Ru1 71.83(19) . . ?
C6 C1 Ru1 69.65(19) . . ?
C1 C2 C3 121.9(3) . . ?
C1 C2 Ru1 72.5(2) . . ?
C3 C2 Ru1 71.15(18) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 Ru1 72.36(18) . . ?
C2 C3 Ru1 72.45(18) . . ?
C3 C4 C5 118.1(3) . . ?
C3 C4 C7 124.3(3) . . ?
C5 C4 C7 117.6(3) . . ?
C3 C4 Ru1 71.35(17) . . ?
C5 C4 Ru1 70.55(19) . . ?
C7 C4 Ru1 131.7(2) . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 Ru1 70.2(2) . . ?
C4 C5 Ru1 71.69(19) . . ?
C1 C6 C5 120.1(3) . . ?
C1 C6 Ru1 73.49(19) . . ?
C5 C6 Ru1 71.86(19) . . ?
C4 C7 C8 117.1(3) . . ?
C9 C8 C7 113.5(3) . . ?
O1 C9 C8 110.6(3) . . ?
C11 C10 C12 111.8(3) . . ?
C11 C10 P1 112.4(2) . . ?
C12 C10 P1 115.6(2) . . ?
C15 C13 C14 110.2(3) . . ?
C15 C13 P1 112.1(3) . . ?
C14 C13 P1 114.8(2) . . ?
C9 O1 P1 116.94(18) . . ?
O1 P1 C13 100.25(13) . . ?
O1 P1 C10 103.03(12) . . ?
C13 P1 C10 106.83(16) . . ?
O1 P1 Ru1 112.99(8) . . ?
C13 P1 Ru1 116.38(11) . . ?
C10 P1 Ru1 115.51(11) . . ?
C6 Ru1 C5 37.98(14) . . ?
C6 Ru1 C3 78.51(13) . . ?
C5 Ru1 C3 66.24(13) . . ?
C6 Ru1 C4 68.14(13) . . ?
C5 Ru1 C4 37.77(13) . . ?
C3 Ru1 C4 36.30(13) . . ?
C6 Ru1 C2 65.43(15) . . ?
C5 Ru1 C2 77.70(14) . . ?
C3 Ru1 C2 36.40(13) . . ?
C4 Ru1 C2 65.72(13) . . ?
C6 Ru1 C1 36.86(15) . . ?
C5 Ru1 C1 66.93(13) . . ?
C3 Ru1 C1 65.56(12) . . ?
C4 Ru1 C1 78.83(13) . . ?
C2 Ru1 C1 35.68(14) . . ?
C6 Ru1 P1 131.68(12) . . ?
C5 Ru1 P1 101.15(10) . . ?
C3 Ru1 P1 112.43(9) . . ?
C4 Ru1 P1 92.89(9) . . ?
C2 Ru1 P1 146.95(10) . . ?
C1 Ru1 P1 167.91(10) . . ?
C6 Ru1 Cl1 136.76(12) . . ?
C5 Ru1 Cl1 160.96(9) . . ?
C3 Ru1 Cl1 95.46(9) . . ?
C4 Ru1 Cl1 127.56(10) . . ?
C2 Ru1 Cl1 84.32(10) . . ?
C1 Ru1 Cl1 101.55(10) . . ?
P1 Ru1 Cl1 90.47(3) . . ?
C6 Ru1 Cl2 87.51(10) . . ?
C5 Ru1 Cl2 108.49(10) . . ?
C3 Ru1 Cl2 162.37(9) . . ?
C4 Ru1 Cl2 145.06(10) . . ?
C2 Ru1 Cl2 127.24(10) . . ?
C1 Ru1 Cl2 96.82(10) . . ?
P1 Ru1 Cl2 84.89(3) . . ?
Cl1 Ru1 Cl2 87.36(3) . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.753
_refine_diff_density_rms         0.146

_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_10a
_database_code_depnum_ccdc_archive 'CCDC 1958495'
loop_
_audit_author_name
_audit_author_address
'Victorio Cadierno'
;Universidad de Oviedo
Spain
;
_audit_update_record             
;
2019-10-10 deposited with the CCDC.	2019-12-02 downloaded from the CCDC.
;
#======================================================================= 

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H21 Cl2 O1 P1 Ru1'
_chemical_formula_sum            'C13 H21 Cl2 O P Ru'
_chemical_formula_weight         396.24

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -y, -z'

_cell_length_a                   7.2966(3)
_cell_length_b                   7.6884(3)
_cell_length_c                   15.4349(6)
_cell_angle_alpha                85.087(3)
_cell_angle_beta                 81.257(4)
_cell_angle_gamma                62.338(4)
_cell_volume                     757.89(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5736
_cell_measurement_theta_min      5.7640
_cell_measurement_theta_max      69.2160

_exptl_crystal_description       blocks
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.736
_exptl_crystal_F_000             400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    12.494
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.20855
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (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            7155
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.897
_diffrn_reflns_theta_max         69.406
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2819
_reflns_number_gt                2674
_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)+(0.1106P)²+0.0100P] 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         2819
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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
C1 C 0.9654(7) 0.2658(7) 0.0150(3) 0.0312(9) Uani 1 1 d . . . . .
H1 H 0.9485 0.3526 -0.0342 0.037 Uiso 1 1 calc R U . . .
C2 C 0.7872(7) 0.2704(6) 0.0705(3) 0.0295(9) Uani 1 1 d . . . . .
H2 H 0.6512 0.3661 0.0599 0.035 Uiso 1 1 calc R U . . .
C3 C 0.8112(7) 0.1341(6) 0.1409(3) 0.0294(9) Uani 1 1 d . . . . .
H3 H 0.6925 0.1300 0.1742 0.035 Uiso 1 1 calc R U . . .
C4 C 1.0160(7) 0.0029(6) 0.1612(3) 0.0268(8) Uani 1 1 d . . . . .
C5 C 1.1940(7) -0.0014(6) 0.1064(3) 0.0287(9) Uani 1 1 d . . . . .
H5 H 1.3308 -0.0924 0.1180 0.034 Uiso 1 1 calc R U . . .
C6 C 1.1635(7) 0.1327(7) 0.0342(3) 0.0333(10) Uani 1 1 d . . . . .
H6 H 1.2819 0.1311 -0.0019 0.040 Uiso 1 1 calc R U . . .
C7 C 1.0403(8) -0.1154(6) 0.2457(3) 0.0313(9) Uani 1 1 d . . . . .
H7A H 0.9650 -0.1950 0.2478 0.038 Uiso 1 1 calc R U . . .
H7B H 1.1897 -0.2060 0.2486 0.038 Uiso 1 1 calc R U . . .
C8 C 1.2047(7) 0.1711(6) 0.3606(3) 0.0274(9) Uani 1 1 d . . . . .
H8 H 1.2197 0.2943 0.3577 0.033 Uiso 1 1 calc R U . . .
C9 C 1.4021(7) 0.0120(6) 0.3112(3) 0.0323(10) Uani 1 1 d . . . . .
H9A H 1.5243 -0.0054 0.3370 0.048 Uiso 1 1 calc R U . . .
H9B H 1.4148 0.0516 0.2494 0.048 Uiso 1 1 calc R U . . .
H9C H 1.3935 -0.1120 0.3155 0.048 Uiso 1 1 calc R U . . .
C10 C 1.1846(8) 0.1090(7) 0.4566(3) 0.0369(10) Uani 1 1 d . . . . .
H10A H 1.1705 -0.0122 0.4609 0.055 Uiso 1 1 calc R U . . .
H10B H 1.0611 0.2131 0.4887 0.055 Uiso 1 1 calc R U . . .
H10C H 1.3093 0.0864 0.4819 0.055 Uiso 1 1 calc R U . . .
C11 C 0.7513(7) 0.3718(6) 0.3852(3) 0.0277(9) Uani 1 1 d . . . . .
H11 H 0.7589 0.2938 0.4410 0.033 Uiso 1 1 calc R U . . .
C12 C 0.5451(7) 0.4191(7) 0.3515(3) 0.0339(10) Uani 1 1 d . . . . .
H12A H 0.4276 0.5014 0.3940 0.051 Uiso 1 1 calc R U . . .
H12B H 0.5391 0.2966 0.3441 0.051 Uiso 1 1 calc R U . . .
H12C H 0.5371 0.4894 0.2951 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7622(7) 0.5575(6) 0.4056(3) 0.0313(10) Uani 1 1 d . . . . .
H13A H 0.7616 0.6341 0.3515 0.047 Uiso 1 1 calc R U . . .
H13B H 0.8907 0.5211 0.4311 0.047 Uiso 1 1 calc R U . . .
H13C H 0.6413 0.6365 0.4475 0.047 Uiso 1 1 calc R U . . .
O1 O 0.9575(5) 0.0147(4) 0.31949(19) 0.0285(7) Uani 1 1 d . . . . .
P1 P 0.97473(15) 0.22103(14) 0.30714(6) 0.0215(3) Uani 1 1 d . . . . .
Cl1 Cl 0.73952(15) 0.63459(14) 0.17279(7) 0.0281(3) Uani 1 1 d . . . . .
Cl2 Cl 1.25064(15) 0.39779(15) 0.16332(7) 0.0292(3) Uani 1 1 d . . . . .
Ru1 Ru 0.98917(4) 0.29087(4) 0.15888(2) 0.02105(18) 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
C1 C6 1.389(7) . ?
C1 C2 1.432(7) . ?
C1 Ru1 2.284(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.415(6) . ?
C2 Ru1 2.218(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.428(6) . ?
C3 Ru1 2.199(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.427(6) . ?
C4 C7 1.508(6) . ?
C4 Ru1 2.128(4) . ?
C5 C6 1.421(7) . ?
C5 Ru1 2.183(4) . ?
C5 H5 0.9500 . ?
C6 Ru1 2.240(4) . ?
C6 H6 0.9500 . ?
C7 O1 1.445(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C10 1.524(6) . ?
C8 C9 1.530(6) . ?
C8 P1 1.847(4) . ?
C8 H8 1.0000 . ?
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 C13 1.527(6) . ?
C11 C12 1.538(6) . ?
C11 P1 1.828(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O1 P1 1.641(3) . ?
P1 Ru1 2.3032(10) . ?
Cl1 Ru1 2.4201(10) . ?
Cl2 Ru1 2.4137(10) . ?

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
C6 C1 C2 119.0(4) . . ?
C6 C1 Ru1 70.4(2) . . ?
C2 C1 Ru1 69.0(2) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
Ru1 C1 H1 133.2 . . ?
C3 C2 C1 120.7(4) . . ?
C3 C2 Ru1 70.6(2) . . ?
C1 C2 Ru1 74.0(2) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
Ru1 C2 H2 128.0 . . ?
C2 C3 C4 119.2(4) . . ?
C2 C3 Ru1 72.1(2) . . ?
C4 C3 Ru1 68.1(2) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
Ru1 C3 H3 132.3 . . ?
C5 C4 C3 120.0(4) . . ?
C5 C4 C7 120.7(4) . . ?
C3 C4 C7 119.1(4) . . ?
C5 C4 Ru1 72.7(2) . . ?
C3 C4 Ru1 73.5(2) . . ?
C7 C4 Ru1 120.3(3) . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 Ru1 73.5(2) . . ?
C4 C5 Ru1 68.6(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
Ru1 C5 H5 129.7 . . ?
C1 C6 C5 121.8(4) . . ?
C1 C6 Ru1 73.9(2) . . ?
C5 C6 Ru1 69.1(2) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
Ru1 C6 H6 130.8 . . ?
O1 C7 C4 109.8(3) . . ?
O1 C7 H7A 109.7 . . ?
C4 C7 H7A 109.7 . . ?
O1 C7 H7B 109.7 . . ?
C4 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
C10 C8 C9 109.4(4) . . ?
C10 C8 P1 112.8(3) . . ?
C9 C8 P1 110.2(3) . . ?
C10 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
P1 C8 H8 108.1 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C11 C12 112.0(4) . . ?
C13 C11 P1 110.6(3) . . ?
C12 C11 P1 110.9(3) . . ?
C13 C11 H11 107.7 . . ?
C12 C11 H11 107.7 . . ?
P1 C11 H11 107.7 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 O1 P1 117.2(3) . . ?
O1 P1 C11 99.34(18) . . ?
O1 P1 C8 104.18(18) . . ?
C11 P1 C8 104.5(2) . . ?
O1 P1 Ru1 106.03(11) . . ?
C11 P1 Ru1 122.18(14) . . ?
C8 P1 Ru1 117.66(15) . . ?
C4 Ru1 C5 38.64(17) . . ?
C4 Ru1 C3 38.48(17) . . ?
C5 Ru1 C3 68.70(16) . . ?
C4 Ru1 C2 68.63(16) . . ?
C5 Ru1 C2 80.15(17) . . ?
C3 Ru1 C2 37.35(17) . . ?
C4 Ru1 C6 68.28(17) . . ?
C5 Ru1 C6 37.44(17) . . ?
C3 Ru1 C6 79.20(17) . . ?
C2 Ru1 C6 66.07(17) . . ?
C4 Ru1 C1 80.23(17) . . ?
C5 Ru1 C1 66.65(17) . . ?
C3 Ru1 C1 66.96(17) . . ?
C2 Ru1 C1 37.05(17) . . ?
C6 Ru1 C1 35.73(18) . . ?
C4 Ru1 P1 78.90(12) . . ?
C5 Ru1 P1 100.74(13) . . ?
C3 Ru1 P1 91.58(12) . . ?
C2 Ru1 P1 125.48(12) . . ?
C6 Ru1 P1 137.72(13) . . ?
C1 Ru1 P1 157.68(13) . . ?
C4 Ru1 Cl2 130.40(12) . . ?
C5 Ru1 Cl2 98.29(12) . . ?
C3 Ru1 Cl2 166.96(12) . . ?
C2 Ru1 Cl2 142.44(12) . . ?
C6 Ru1 Cl2 89.83(13) . . ?
C1 Ru1 Cl2 107.75(13) . . ?
P1 Ru1 Cl2 91.87(4) . . ?
C4 Ru1 Cl1 143.19(12) . . ?
C5 Ru1 Cl1 163.03(13) . . ?
C3 Ru1 Cl1 106.41(12) . . ?
C2 Ru1 Cl1 86.59(12) . . ?
C6 Ru1 Cl1 126.68(13) . . ?
C1 Ru1 Cl1 96.40(12) . . ?
P1 Ru1 Cl1 95.56(4) . . ?
Cl2 Ru1 Cl1 85.77(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -3.6(6) . . . . ?
Ru1 C1 C2 C3 -55.0(4) . . . . ?
C6 C1 C2 Ru1 51.4(4) . . . . ?
C1 C2 C3 C4 5.7(6) . . . . ?
Ru1 C2 C3 C4 -50.9(3) . . . . ?
C1 C2 C3 Ru1 56.6(4) . . . . ?
C2 C3 C4 C5 -5.3(6) . . . . ?
Ru1 C3 C4 C5 -58.1(3) . . . . ?
C2 C3 C4 C7 168.7(4) . . . . ?
Ru1 C3 C4 C7 116.0(4) . . . . ?
C2 C3 C4 Ru1 52.8(4) . . . . ?
C3 C4 C5 C6 2.9(6) . . . . ?
C7 C4 C5 C6 -171.1(4) . . . . ?
Ru1 C4 C5 C6 -55.6(4) . . . . ?
C3 C4 C5 Ru1 58.4(3) . . . . ?
C7 C4 C5 Ru1 -115.5(4) . . . . ?
C2 C1 C6 C5 1.1(7) . . . . ?
Ru1 C1 C6 C5 51.9(4) . . . . ?
C2 C1 C6 Ru1 -50.7(4) . . . . ?
C4 C5 C6 C1 -0.8(7) . . . . ?
Ru1 C5 C6 C1 -54.0(4) . . . . ?
C4 C5 C6 Ru1 53.2(4) . . . . ?
C5 C4 C7 O1 110.5(4) . . . . ?
C3 C4 C7 O1 -63.4(5) . . . . ?
Ru1 C4 C7 O1 23.6(5) . . . . ?
C4 C7 O1 P1 -31.6(5) . . . . ?
C7 O1 P1 C11 152.9(3) . . . . ?
C7 O1 P1 C8 -99.4(3) . . . . ?
C7 O1 P1 Ru1 25.4(3) . . . . ?
C13 C11 P1 O1 164.9(3) . . . . ?
C12 C11 P1 O1 -70.2(3) . . . . ?
C13 C11 P1 C8 57.5(3) . . . . ?
C12 C11 P1 C8 -177.6(3) . . . . ?
C13 C11 P1 Ru1 -79.3(3) . . . . ?
C12 C11 P1 Ru1 45.6(4) . . . . ?
C10 C8 P1 O1 -57.9(3) . . . . ?
C9 C8 P1 O1 64.7(3) . . . . ?
C10 C8 P1 C11 45.9(4) . . . . ?
C9 C8 P1 C11 168.5(3) . . . . ?
C10 C8 P1 Ru1 -174.9(3) . . . . ?
C9 C8 P1 Ru1 -52.3(3) . . . . ?

_refine_diff_density_max         0.998
_refine_diff_density_min         -1.789
_refine_diff_density_rms         0.206

_shelxl_version_number           2014-3

