#------------------------------------------------------------------------------
#$Date: 2016-05-06 04:15:54 +0300 (Fri, 06 May 2016) $
#$Revision: 182686 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/85/7038586.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_7038586
loop_
_publ_author_name
'Graux, Lionel V.'
'Giorgi, Michel'
'Buono, Gérard'
'Clavier, Hervé'
_publ_section_title
;
 [RuCl2(η(6)-p-cymene)] complexes bearing phosphinous acid ligands:
 preparation, application in C-H bond functionalization and mechanistic
 investigations.
;
_journal_issue                   15
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              6491
_journal_page_last               6502
_journal_paper_doi               10.1039/c5dt04683a
_journal_volume                  45
_journal_year                    2016
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C17 H23 Cl2 O1 P1 Ru1'
_chemical_formula_sum            'C17 H23 Cl2 O P Ru'
_chemical_formula_weight         446.29
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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             2013-01-28T14:39:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-10-29 deposited with the CCDC.
2016-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.723(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6118(1)
_cell_length_b                   12.0417(2)
_cell_length_c                   17.5332(3)
_cell_measurement_reflns_used    18725
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      2.74
_cell_measurement_wavelength     0.71073
_cell_volume                     1885.22(5)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.964
_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  0.0454
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            18725
_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        25
_diffrn_reflns_theta_max         29.5
_diffrn_reflns_theta_min         2.74
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.198
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_correction_T_min  0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         5072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.963
_refine_ls_R_factor_all          0.063
_refine_ls_R_factor_gt           0.0337
_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)+(0.0316P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0767
_reflns_number_gt                3572
_reflns_number_total             5072
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5dt04683a2.cif
_cod_data_source_block           mo010
_cod_depositor_comments
'Adding full bibliography for 7038583--7038589.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C17 H23 Cl2 O1 P1 Ru1'
_cod_database_code               7038586
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.9347(3) 0.2680(2) 1.34265(17) 0.0511(7) Uani 1 1 d .
H1 H 1.013 0.3189 1.3573 0.061 Uiso 1 1 calc R
C2 C 0.9473(3) 0.1720(3) 1.39127(16) 0.0510(7) Uani 1 1 d .
C3 C 0.8299(3) 0.0964(2) 1.36696(17) 0.0493(7) Uani 1 1 d .
H3 H 0.8358 0.0323 1.3976 0.059 Uiso 1 1 calc R
C4 C 0.7018(3) 0.1165(2) 1.29587(18) 0.0471(7) Uani 1 1 d .
H4 H 0.6267 0.063 1.2797 0.057 Uiso 1 1 calc R
C5 C 0.6823(3) 0.2129(2) 1.24847(16) 0.0447(6) Uani 1 1 d .
C6 C 0.8057(3) 0.2877(2) 1.27258(17) 0.0499(7) Uani 1 1 d .
H6 H 0.8009 0.3509 1.2413 0.06 Uiso 1 1 calc R
C7 C 1.0874(4) 0.1496(3) 1.46477(18) 0.0748(11) Uani 1 1 d .
H7A H 1.0712 0.1692 1.5139 0.112 Uiso 1 1 calc R
H7B H 1.1683 0.193 1.4609 0.112 Uiso 1 1 calc R
H7C H 1.1121 0.0721 1.4664 0.112 Uiso 1 1 calc R
C8 C 0.5401(3) 0.2394(3) 1.1758(2) 0.0653(9) Uani 1 1 d .
H8 H 0.5696 0.2694 1.1321 0.078 Uiso 1 1 calc R
C9 C 0.4564(5) 0.3311(5) 1.2019(3) 0.130(2) Uani 1 1 d .
H9A H 0.4341 0.3062 1.2481 0.195 Uiso 1 1 calc R
H9B H 0.3648 0.348 1.1571 0.195 Uiso 1 1 calc R
H9C H 0.5177 0.3964 1.2167 0.195 Uiso 1 1 calc R
C10 C 0.4418(4) 0.1394(4) 1.1417(3) 0.1120(18) Uani 1 1 d .
H10A H 0.3896 0.1205 1.1772 0.168 Uiso 1 1 calc R
H10B H 0.5027 0.0778 1.1384 0.168 Uiso 1 1 calc R
H10C H 0.3706 0.1563 1.0879 0.168 Uiso 1 1 calc R
C11 C 0.7658(3) 0.2315(2) 1.05745(14) 0.0409(6) Uani 1 1 d .
C12 C 0.7350(4) 0.3440(3) 1.04267(18) 0.0591(8) Uani 1 1 d .
H12 H 0.8015 0.3971 1.0744 0.071 Uiso 1 1 calc R
C13 C 0.6036(5) 0.3757(4) 0.9797(2) 0.0837(13) Uani 1 1 d .
H13 H 0.582 0.4507 0.9691 0.1 Uiso 1 1 calc R
C14 C 0.5056(5) 0.2975(6) 0.9333(2) 0.1045(18) Uani 1 1 d .
H14 H 0.4173 0.3196 0.8917 0.125 Uiso 1 1 calc R
C15 C 0.5366(4) 0.1879(5) 0.9476(2) 0.0978(14) Uani 1 1 d .
H15 H 0.4698 0.1354 0.9151 0.117 Uiso 1 1 calc R
C16 C 0.6661(3) 0.1532(3) 1.00966(19) 0.0651(9) Uani 1 1 d .
H16 H 0.6862 0.0779 1.0193 0.078 Uiso 1 1 calc R
C17 C 1.0133(3) 0.0882(3) 1.09315(17) 0.0516(7) Uani 1 1 d .
H17A H 1.0251 0.1222 1.0464 0.077 Uiso 1 1 calc R
H17B H 0.9487 0.0248 1.0756 0.077 Uiso 1 1 calc R
H17C H 1.1093 0.065 1.1314 0.077 Uiso 1 1 calc R
O1 O 1.0409(2) 0.29177(17) 1.15452(11) 0.0550(5) Uani 1 1 d .
H1W H 1.0708 0.3237 1.1958 0.083 Uiso 1 1 d R
P1 P 0.93201(7) 0.18681(5) 1.14197(4) 0.03417(15) Uani 1 1 d .
Cl1 Cl 1.15110(7) 0.06899(6) 1.29771(4) 0.04818(17) Uani 1 1 d .
Cl2 Cl 0.81673(7) -0.04937(5) 1.19156(4) 0.04637(16) Uani 1 1 d .
Ru1 Ru 0.89530(2) 0.127913(15) 1.258687(11) 0.03088(7) 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 0.0033 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 121.0(3)
C6 C1 Ru1 70.32(15)
C2 C1 Ru1 74.26(16)
C6 C1 H1 119.5
C2 C1 H1 119.5
Ru1 C1 H1 128.1
C3 C2 C1 118.2(3)
C3 C2 C7 120.9(3)
C1 C2 C7 120.9(3)
C3 C2 Ru1 71.57(15)
C1 C2 Ru1 68.54(14)
C7 C2 Ru1 128.9(2)
C2 C3 C4 120.2(3)
C2 C3 Ru1 72.44(15)
C4 C3 Ru1 69.47(15)
C2 C3 H3 119.9
C4 C3 H3 119.9
Ru1 C3 H3 130.8
C5 C4 C3 123.2(3)
C5 C4 Ru1 73.34(15)
C3 C4 Ru1 73.41(15)
C5 C4 H4 118.4
C3 C4 H4 118.4
Ru1 C4 H4 127
C4 C5 C6 115.8(2)
C4 C5 C8 123.6(3)
C6 C5 C8 120.6(3)
C4 C5 Ru1 69.81(15)
C6 C5 Ru1 68.16(14)
C8 C5 Ru1 132.60(18)
C1 C6 C5 121.5(3)
C1 C6 Ru1 71.87(15)
C5 C6 Ru1 74.10(15)
C1 C6 H6 119.3
C5 C6 H6 119.3
Ru1 C6 H6 126.8
C2 C7 H7A 109.5
C2 C7 H7B 109.5
H7A C7 H7B 109.5
C2 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C10 C8 C5 113.7(3)
C10 C8 C9 111.8(3)
C5 C8 C9 108.1(3)
C10 C8 H8 107.7
C5 C8 H8 107.7
C9 C8 H8 107.7
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
C16 C11 C12 120.0(3)
C16 C11 P1 119.7(2)
C12 C11 P1 120.3(2)
C13 C12 C11 119.0(3)
C13 C12 H12 120.5
C11 C12 H12 120.5
C14 C13 C12 120.5(4)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 120.3(4)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 120.8(4)
C14 C15 H15 119.6
C16 C15 H15 119.6
C15 C16 C11 119.4(4)
C15 C16 H16 120.3
C11 C16 H16 120.3
P1 C17 H17A 109.5
P1 C17 H17B 109.5
H17A C17 H17B 109.5
P1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
P1 O1 H1W 121.1
O1 P1 C17 102.06(13)
O1 P1 C11 102.19(12)
C17 P1 C11 102.31(13)
O1 P1 Ru1 115.21(7)
C17 P1 Ru1 116.94(10)
C11 P1 Ru1 115.94(9)
C6 Ru1 C1 37.81(10)
C6 Ru1 C4 66.69(10)
C1 Ru1 C4 78.58(11)
C6 Ru1 C5 37.74(10)
C1 Ru1 C5 67.95(11)
C4 Ru1 C5 36.85(10)
C6 Ru1 C3 78.87(10)
C1 Ru1 C3 65.93(11)
C4 Ru1 C3 37.12(10)
C5 Ru1 C3 67.06(10)
C6 Ru1 C2 67.60(11)
C1 Ru1 C2 37.20(11)
C4 Ru1 C2 66.19(11)
C5 Ru1 C2 79.73(10)
C3 Ru1 C2 35.99(11)
C6 Ru1 P1 91.40(7)
C1 Ru1 P1 108.37(8)
C4 Ru1 P1 134.98(8)
C5 Ru1 P1 102.93(7)
C3 Ru1 P1 169.58(8)
C2 Ru1 P1 142.41(8)
C6 Ru1 Cl1 129.81(8)
C1 Ru1 Cl1 97.63(8)
C4 Ru1 Cl1 142.06(8)
C5 Ru1 Cl1 165.52(8)
C3 Ru1 Cl1 106.67(8)
C2 Ru1 Cl1 87.88(8)
P1 Ru1 Cl1 82.38(2)
C6 Ru1 Cl2 140.87(8)
C1 Ru1 Cl2 163.14(8)
C4 Ru1 Cl2 86.72(8)
C5 Ru1 Cl2 104.67(8)
C3 Ru1 Cl2 97.33(8)
C2 Ru1 Cl2 128.31(8)
P1 Ru1 Cl2 87.85(2)
Cl1 Ru1 Cl2 88.87(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.405(4)
C1 C2 1.415(4)
C1 Ru1 2.178(3)
C1 H1 0.93
C2 C3 1.388(4)
C2 C7 1.504(4)
C2 Ru1 2.253(2)
C3 C4 1.412(4)
C3 Ru1 2.242(3)
C3 H3 0.93
C4 C5 1.400(4)
C4 Ru1 2.191(3)
C4 H4 0.93
C5 C6 1.423(4)
C5 C8 1.517(4)
C5 Ru1 2.236(2)
C6 Ru1 2.158(3)
C6 H6 0.93
C7 H7A 0.96
C7 H7B 0.96
C7 H7C 0.96
C8 C10 1.511(5)
C8 C9 1.532(5)
C8 H8 0.98
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 C16 1.384(4)
C11 C12 1.390(4)
C11 P1 1.813(2)
C12 C13 1.389(5)
C12 H12 0.93
C13 C14 1.367(7)
C13 H13 0.93
C14 C15 1.356(7)
C14 H14 0.93
C15 C16 1.381(5)
C15 H15 0.93
C16 H16 0.93
C17 P1 1.802(3)
C17 H17A 0.96
C17 H17B 0.96
C17 H17C 0.96
O1 P1 1.6034(19)
O1 H1W 0.7757
P1 Ru1 2.3130(6)
Cl1 Ru1 2.4024(6)
Cl2 Ru1 2.4197(6)
