#------------------------------------------------------------------------------
#$Date: 2016-03-21 15:23:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178745 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/56/4085644.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4085644
loop_
_publ_author_name
'Tsui, Wai-Kuen'
'Chung, Lai-Hon'
'Tsang, Wai-Him'
'Yeung, Chi-Fung'
'Chiu, Chun-Hong'
'Lo, Hoi-Shing'
'Wong, Chun-Yuen'
_publ_section_title
;
 Synthesis, Spectroscopic and Theoretical Studies of Ruthenafuran and
 Osmafuran Prepared by Activation of Ynone in Alcohol
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1005
_journal_paper_doi               10.1021/acs.organomet.5b00009
_journal_volume                  34
_journal_year                    2015
_chemical_formula_sum            'C20 H29 Cl O6 Ru S4'
_chemical_formula_weight         630.19
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                75.480(3)
_cell_angle_beta                 71.716(4)
_cell_angle_gamma                78.169(3)
_cell_formula_units_Z            2
_cell_length_a                   9.4805(4)
_cell_length_b                   11.4022(4)
_cell_length_c                   12.9735(4)
_cell_measurement_reflns_used    5634
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      71.5217
_cell_measurement_theta_min      3.6595
_cell_volume                     1276.84(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 16.1270
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8568
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         3.66
_exptl_absorpt_coefficient_mu    9.282
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.381
_refine_diff_density_min         -0.979
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0500P)²+1.9015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                4333
_reflns_number_total             4571
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00009_si_001.cif
_cod_data_source_block           COMPLEX_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 
;
_cod_original_cell_volume        1276.84(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4085644
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.0732(3) 0.3066(3) 0.0899(2) 0.0263(6) Uani 1 1 d .
C2 C 0.1625(3) 0.4004(3) 0.0512(2) 0.0275(6) Uani 1 1 d .
H2 H 0.1978 0.4345 -0.0235 0.033 Uiso 1 1 calc R
C3 C 0.1943(3) 0.4386(3) 0.1355(2) 0.0268(6) Uani 1 1 d .
C4 C 0.2901(3) 0.5347(3) 0.1149(3) 0.0284(6) Uani 1 1 d .
C5 C 0.3393(4) 0.6078(3) 0.0110(3) 0.0363(7) Uani 1 1 d .
H5 H 0.3112 0.5979 -0.0485 0.044 Uiso 1 1 calc R
C6 C 0.4300(4) 0.6955(3) -0.0045(3) 0.0423(8) Uani 1 1 d .
H6 H 0.4621 0.7442 -0.0742 0.051 Uiso 1 1 calc R
C7 C 0.4731(4) 0.7108(3) 0.0833(3) 0.0421(8) Uani 1 1 d .
H7 H 0.5340 0.7697 0.0726 0.051 Uiso 1 1 calc R
C8 C 0.4255(5) 0.6384(4) 0.1866(3) 0.0472(9) Uani 1 1 d .
H8 H 0.4546 0.6481 0.2457 0.057 Uiso 1 1 calc R
C9 C 0.3341(4) 0.5511(3) 0.2023(3) 0.0413(8) Uani 1 1 d .
H9 H 0.3019 0.5028 0.2723 0.050 Uiso 1 1 calc R
C10 C 0.0813(4) 0.3060(3) -0.0971(3) 0.0382(7) Uani 1 1 d .
H10A H 0.0545 0.3932 -0.1134 0.057 Uiso 1 1 calc R
H10B H 0.0358 0.2688 -0.1350 0.057 Uiso 1 1 calc R
H10C H 0.1883 0.2861 -0.1214 0.057 Uiso 1 1 calc R
C11 C -0.3428(4) 0.2610(4) 0.3076(4) 0.0538(10) Uani 1 1 d .
H11A H -0.3639 0.2265 0.3864 0.065 Uiso 1 1 calc R
H11B H -0.4362 0.3020 0.2917 0.065 Uiso 1 1 calc R
C12 C -0.2755(4) 0.1608(3) 0.2421(4) 0.0465(9) Uani 1 1 d .
H12A H -0.2524 0.1949 0.1633 0.056 Uiso 1 1 calc R
H12B H -0.3450 0.1023 0.2598 0.056 Uiso 1 1 calc R
C13 C -0.0094(4) -0.0075(3) 0.1806(3) 0.0464(9) Uani 1 1 d .
H13A H -0.0723 -0.0658 0.1829 0.056 Uiso 1 1 calc R
H13B H 0.0146 0.0425 0.1065 0.056 Uiso 1 1 calc R
C14 C 0.1344(5) -0.0746(4) 0.2097(4) 0.0594(11) Uani 1 1 d .
H14A H 0.1105 -0.1027 0.2895 0.071 Uiso 1 1 calc R
H14B H 0.1664 -0.1466 0.1768 0.071 Uiso 1 1 calc R
C15 C 0.2663(5) -0.0026(4) 0.1738(4) 0.0591(11) Uani 1 1 d .
H15A H 0.2873 0.0271 0.0943 0.071 Uiso 1 1 calc R
H15B H 0.3529 -0.0596 0.1870 0.071 Uiso 1 1 calc R
C16 C 0.2528(5) 0.0580(4) 0.3802(4) 0.0629(13) Uani 1 1 d .
H16A H 0.1944 -0.0096 0.4081 0.075 Uiso 1 1 calc R
H16B H 0.3546 0.0269 0.3841 0.075 Uiso 1 1 calc R
C17 C 0.1859(6) 0.1544(5) 0.4488(4) 0.0630(13) Uani 1 1 d .
H17A H 0.2386 0.2252 0.4171 0.076 Uiso 1 1 calc R
H17B H 0.1945 0.1229 0.5237 0.076 Uiso 1 1 calc R
C18 C -0.0631(7) 0.3425(5) 0.4923(4) 0.0687(14) Uani 1 1 d .
H18A H -0.0542 0.3343 0.5664 0.082 Uiso 1 1 calc R
H18B H 0.0010 0.4010 0.4418 0.082 Uiso 1 1 calc R
C19 C -0.2245(8) 0.3854(6) 0.4901(5) 0.094(2) Uani 1 1 d .
H19A H -0.2775 0.3146 0.5199 0.113 Uiso 1 1 calc R
H19B H -0.2676 0.4410 0.5411 0.113 Uiso 1 1 calc R
C20 C -0.2581(7) 0.4461(5) 0.3851(4) 0.0756(15) Uani 1 1 d .
H20A H -0.2109 0.5199 0.3588 0.091 Uiso 1 1 calc R
H20B H -0.3655 0.4720 0.4024 0.091 Uiso 1 1 calc R
Cl5 Cl 0.62326(10) 0.80484(9) 0.35372(9) 0.0508(2) Uani 1 1 d .
O1 O 0.1388(3) 0.3903(2) 0.23687(17) 0.0330(5) Uani 1 1 d .
O2 O 0.0288(3) 0.2609(2) 0.02116(18) 0.0330(5) Uani 1 1 d .
O3 O 0.5374(7) 0.7125(5) 0.4012(7) 0.177(3) Uani 1 1 d .
O4 O 0.6032(5) 0.8622(6) 0.2438(4) 0.122(2) Uani 1 1 d .
O5 O 0.7799(3) 0.7615(3) 0.3379(2) 0.0589(7) Uani 1 1 d .
O6 O 0.5767(4) 0.8980(3) 0.4167(3) 0.0686(9) Uani 1 1 d .
Ru1 Ru 0.02101(2) 0.246500(19) 0.254159(17) 0.02649(10) Uani 1 1 d .
S1 S -0.20875(10) 0.37024(7) 0.26865(7) 0.0385(2) Uani 1 1 d .
S2 S -0.10576(9) 0.08737(7) 0.28067(7) 0.03331(18) Uani 1 1 d .
S3 S 0.25281(10) 0.12627(8) 0.23562(8) 0.0439(2) Uani 1 1 d .
S4 S -0.00889(12) 0.19672(9) 0.45074(7) 0.0465(2) Uani 1 1 d .
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O2 C1 C2 122.0(3)
O2 C1 Ru1 123.8(2)
C2 C1 Ru1 114.2(2)
C1 C2 C3 113.9(3)
O1 C3 C2 119.9(3)
O1 C3 C4 116.1(3)
C2 C3 C4 124.0(3)
C9 C4 C5 118.7(3)
C9 C4 C3 118.9(3)
C5 C4 C3 122.4(3)
C6 C5 C4 120.4(3)
C7 C6 C5 120.4(3)
C8 C7 C6 119.7(3)
C7 C8 C9 120.0(4)
C8 C9 C4 120.9(3)
C12 C11 S1 108.5(3)
C11 C12 S2 106.5(3)
C14 C13 S2 107.7(3)
C15 C14 C13 116.8(3)
C14 C15 S3 119.5(3)
C17 C16 S3 108.7(3)
C16 C17 S4 108.0(3)
C19 C18 S4 107.2(4)
C20 C19 C18 119.8(5)
C19 C20 S1 122.2(4)
O3 Cl5 O6 110.7(3)
O3 Cl5 O5 112.1(3)
O6 Cl5 O5 110.99(19)
O3 Cl5 O4 109.8(5)
O6 Cl5 O4 106.3(3)
O5 Cl5 O4 106.7(2)
C3 O1 Ru1 112.35(19)
C1 O2 C10 119.0(2)
C1 Ru1 O1 79.26(10)
C1 Ru1 S2 103.19(9)
O1 Ru1 S2 177.46(6)
C1 Ru1 S3 89.83(9)
O1 Ru1 S3 84.99(7)
S2 Ru1 S3 94.32(3)
C1 Ru1 S1 88.89(9)
O1 Ru1 S1 94.17(7)
S2 Ru1 S1 86.58(3)
S3 Ru1 S1 178.58(3)
C1 Ru1 S4 169.56(9)
O1 Ru1 S4 90.58(6)
S2 Ru1 S4 86.95(3)
S3 Ru1 S4 86.88(4)
S1 Ru1 S4 94.28(4)
C20 S1 C11 105.0(2)
C20 S1 Ru1 111.1(2)
C11 S1 Ru1 103.54(13)
C13 S2 C12 104.9(2)
C13 S2 Ru1 110.41(13)
C12 S2 Ru1 103.31(12)
C15 S3 C16 104.6(2)
C15 S3 Ru1 112.33(15)
C16 S3 Ru1 103.03(16)
C18 S4 C17 105.0(3)
C18 S4 Ru1 104.27(15)
C17 S4 Ru1 98.94(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.342(4)
C1 C2 1.396(4)
C1 Ru1 2.000(3)
C2 C3 1.405(4)
C3 O1 1.277(4)
C3 C4 1.486(4)
C4 C9 1.389(5)
C4 C5 1.390(5)
C5 C6 1.387(5)
C6 C7 1.384(6)
C7 C8 1.378(6)
C8 C9 1.387(5)
C10 O2 1.448(4)
C11 C12 1.511(6)
C11 S1 1.831(4)
C12 S2 1.812(4)
C13 C14 1.529(6)
C13 S2 1.801(4)
C14 C15 1.523(6)
C15 S3 1.808(5)
C16 C17 1.502(8)
C16 S3 1.841(4)
C17 S4 1.805(5)
C18 C19 1.515(9)
C18 S4 1.801(5)
C19 C20 1.464(8)
C20 S1 1.815(5)
Cl5 O3 1.365(5)
Cl5 O6 1.417(3)
Cl5 O5 1.432(3)
Cl5 O4 1.466(4)
O1 Ru1 2.097(2)
Ru1 S2 2.2753(8)
Ru1 S3 2.3162(9)
Ru1 S1 2.3209(9)
Ru1 S4 2.4069(9)
