#------------------------------------------------------------------------------
#$Date: 2016-02-13 21:28:24 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176429 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/57/4085723.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_4085723
loop_
_publ_author_name
'Graux, Lionel V.'
'Giorgi, Michel'
'Buono, Gérard'
'Clavier, Hervé'
_publ_section_title
;
 Ruthenium Carbonyl Complexes Bearing Secondary Phosphine Oxides and
 Phosphinous Acids: Synthesis, Characterization, and Application in
 Catalysis
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              1864
_journal_paper_doi               10.1021/om501300p
_journal_volume                  34
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C13 H17 Cl2 O5 P1 Ru1'
_chemical_formula_sum            'C13 H17 Cl2 O5 P Ru'
_chemical_formula_weight         456.21
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2012-01-30T10:26:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 96.244(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.6254(7)
_cell_length_b                   9.4691(4)
_cell_length_c                   12.5686(5)
_cell_measurement_reflns_used    10831
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.51
_cell_measurement_theta_min      2.87
_cell_measurement_wavelength     0.71073
_cell_volume                     2085.21(15)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10831
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        28.51
_diffrn_reflns_theta_max         28.51
_diffrn_reflns_theta_min         2.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.099
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.136
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.094
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0777P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1264
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2869
_reflns_number_total             4432
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            om501300p_si_002.cif
_cod_data_source_block           lgr021
_cod_depositor_comments
'Adding full bibliography for 4085723--4085725.cif.'
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C13 H17 Cl2 O5 P1 Ru1'
_cod_database_code               4085723
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3502(4) 0.8450(8) 0.5612(5) 0.0648(19) Uani 1 1 d . . .
C2 C 0.3836(7) 0.7148(10) 0.5797(8) 0.101(3) Uani 1 1 d . . .
H2 H 0.4002 0.6861 0.6491 0.122 Uiso 1 1 calc R . .
C3 C 0.3924(6) 0.6262(12) 0.4929(10) 0.112(3) Uani 1 1 d . . .
H3 H 0.4156 0.5381 0.5014 0.135 Uiso 1 1 calc R . .
C4 C 0.3626(7) 0.6814(17) 0.3876(9) 0.125(5) Uani 1 1 d . . .
H4 H 0.3674 0.6262 0.3275 0.15 Uiso 1 1 calc R . .
C5 C 0.3302(6) 0.803(2) 0.3744(7) 0.108(3) Uani 1 1 d . . .
H5 H 0.3126 0.8336 0.306 0.129 Uiso 1 1 calc R . .
C6 C 0.3218(6) 0.8837(11) 0.4593(6) 0.092(3) Uani 1 1 d . . .
H6 H 0.296 0.9691 0.4491 0.11 Uiso 1 1 calc R . .
C7 C 0.4195(5) 1.0851(9) 0.6848(6) 0.079(2) Uani 1 1 d . . .
C8 C 0.4093(8) 1.1769(14) 0.7832(9) 0.138(5) Uani 1 1 d . . .
H8A H 0.357 1.2066 0.7805 0.206 Uiso 1 1 calc R . .
H8B H 0.4417 1.2583 0.7834 0.206 Uiso 1 1 calc R . .
H8C H 0.4227 1.1229 0.8472 0.206 Uiso 1 1 calc R . .
C9 C 0.4125(7) 1.1774(11) 0.5825(8) 0.109(3) Uani 1 1 d . . .
H9A H 0.3629 1.2203 0.5729 0.163 Uiso 1 1 calc R . .
H9B H 0.4193 1.1193 0.5216 0.163 Uiso 1 1 calc R . .
H9C H 0.4509 1.2496 0.5895 0.163 Uiso 1 1 calc R . .
C10 C 0.4944(6) 1.0113(14) 0.6896(10) 0.117(4) Uani 1 1 d . . .
H10A H 0.4954 0.9524 0.6276 0.176 Uiso 1 1 calc R . .
H10B H 0.5015 0.954 0.753 0.176 Uiso 1 1 calc R . .
H10C H 0.5347 1.0798 0.6915 0.176 Uiso 1 1 calc R . .
C11 C 0.3132(6) 0.8317(9) 0.9892(6) 0.088(3) Uani 1 1 d . . .
C12 C 0.1688(6) 0.7402(9) 0.9262(6) 0.082(2) Uani 1 1 d . . .
C13 C 0.2861(6) 0.6121(10) 0.8435(7) 0.085(2) Uani 1 1 d . . .
O1 O 0.3442(3) 0.8757(6) 0.7776(4) 0.0722(13) Uani 1 1 d . . .
O2 O 0.3463(5) 0.8617(8) 1.0690(5) 0.117(2) Uani 1 1 d . . .
O3 O 0.1163(5) 0.7029(10) 0.9591(6) 0.125(3) Uani 1 1 d . . .
O4 O 0.3038(5) 0.4987(8) 0.8300(7) 0.125(3) Uani 1 1 d . . .
P1 P 0.34291(10) 0.9583(2) 0.67439(13) 0.0611(4) Uani 1 1 d . . .
H1P H 0.2787 1.0534 0.6345 0.073 Uiso 1 1 d R . .
Cl1 Cl 0.21309(14) 1.0419(2) 0.87310(15) 0.0819(5) Uani 1 1 d . . .
Cl2 Cl 0.17738(11) 0.7781(3) 0.68898(13) 0.0826(6) Uani 1 1 d . . .
Ru1 Ru 0.25311(3) 0.80146(5) 0.85726(3) 0.06292(19) Uani 1 1 d . . .
O5 O 0 0.9349(18) 1 0.079(4) Uiso 0.5 2 d SP A 1
O6 O 0.0233(6) 1.1938(12) 1.1092(8) 0.076(3) Uiso 0.5 1 d P B 2
O8 O 0 1.278(6) 1 0.136(14) Uiso 0.25 2 d SP C 3
O9 O -0.0295(19) 1.075(4) 1.033(3) 0.059(8) Uiso 0.13 1 d P . 4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 120.2(8)
C6 C1 P1 121.9(7)
C2 C1 P1 117.9(6)
C1 C2 C3 119.2(10)
C1 C2 H2 120.4
C3 C2 H2 120.4
C2 C3 C4 115.5(10)
C2 C3 H3 122.2
C4 C3 H3 122.2
C5 C4 C3 123.1(9)
C5 C4 H4 118.5
C3 C4 H4 118.5
C4 C5 C6 119.8(9)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C6 C1 122.0(11)
C5 C6 H6 119
C1 C6 H6 119
C10 C7 C8 114.4(10)
C10 C7 C9 106.9(8)
C8 C7 C9 110.1(9)
C10 C7 P1 110.1(7)
C8 C7 P1 106.4(6)
C9 C7 P1 108.9(6)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O2 C11 Ru1 173.8(8)
O3 C12 Ru1 174.6(8)
O4 C13 Ru1 176.3(9)
P1 O1 Ru1 129.8(3)
O1 P1 C1 112.0(3)
O1 P1 C7 110.0(4)
C1 P1 C7 109.7(3)
O1 P1 H1P 122.7
C1 P1 H1P 102.2
C7 P1 H1P 99.1
C11 Ru1 C12 92.1(4)
C11 Ru1 C13 94.3(4)
C12 Ru1 C13 90.9(4)
C11 Ru1 O1 89.1(3)
C12 Ru1 O1 177.8(3)
C13 Ru1 O1 90.9(3)
C11 Ru1 Cl2 176.6(3)
C12 Ru1 Cl2 89.2(3)
C13 Ru1 Cl2 88.8(3)
O1 Ru1 Cl2 89.50(14)
C11 Ru1 Cl1 85.7(3)
C12 Ru1 Cl1 90.0(3)
C13 Ru1 Cl1 179.1(3)
O1 Ru1 Cl1 88.22(16)
Cl2 Ru1 Cl1 91.17(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.373(11) .
C1 C2 1.375(12) .
C1 P1 1.798(7) .
C2 C3 1.398(13) .
C2 H2 0.93 .
C3 C4 1.467(19) .
C3 H3 0.93 .
C4 C5 1.284(19) .
C4 H4 0.93 .
C5 C6 1.336(17) .
C5 H5 0.93 .
C6 H6 0.93 .
C7 C10 1.489(15) .
C7 C8 1.539(11) .
C7 C9 1.548(13) .
C7 P1 1.801(8) .
C8 H8A 0.96 .
C8 H8B 0.96 .
C8 H8C 0.96 .
C9 H9A 0.96 .
C9 H9B 0.96 .
C9 H9C 0.96 .
C10 H10A 0.96 .
C10 H10B 0.96 .
C10 H10C 0.96 .
C11 O2 1.141(10) .
C11 Ru1 1.890(9) .
C12 O3 1.111(10) .
C12 Ru1 1.891(9) .
C13 O4 1.135(11) .
C13 Ru1 1.899(10) .
O1 P1 1.513(5) .
O1 Ru1 2.103(5) .
P1 H1P 1.4895 .
Cl1 Ru1 2.398(2) .
Cl2 Ru1 2.3853(17) .
O9 O9 1.40(7) 2_557
