#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:58:59 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179087 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/49/4304939.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_4304939
loop_
_publ_author_name
'Julia E. Barker'
'Tong Ren'
_publ_contact_author_address
; Department of Chemistry 
  Purdue University 
  560 Oval Drive 
  West Lafayette, IN 47906 
  USA 
;
_publ_contact_author_email       tren@purdue.edu
_publ_contact_author_fax         '(765) 494-0239'
_publ_contact_author_name        'Dr. Ren, Tong'
_publ_contact_author_phone       '(765) 494-5466'
_publ_section_title
;
Diruthenium(II,III) Bis(tetramethyl-1,3-benzenedipropionate) as a Novel
Catalyst for tert-Butyl Hydroperoxide Oxygenation
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              2264
_journal_page_last               2266
_journal_paper_doi               10.1021/ic800035w
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C34 H44 Cl5 O9 Ru2'
_chemical_formula_weight         976.08
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9347(7)
_cell_length_b                   21.6624(10)
_cell_length_c                   11.2152(5)
_cell_measurement_reflns_used    4645
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      25.27
_cell_measurement_theta_min      2.18
_cell_volume                     4114.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20916
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_exptl_absorpt_coefficient_mu    1.106
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Maroon
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1972
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0367
_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)+(0.0390P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                2551
_reflns_number_total             3729
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic800035w-file001.cif
_cod_data_source_block           um496
_cod_database_code               4304939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 1.05497(2) 0.2500 0.20356(3) 0.03345(13) Uani 1 2 d S . .
Ru2 Ru 0.93545(2) 0.2500 0.11059(4) 0.03493(14) Uani 1 2 d S . .
Cl1 Cl 1.18808(8) 0.2500 0.29685(12) 0.0534(4) Uani 1 2 d S . .
Cl2 Cl 0.76080(17) 0.41903(13) -0.0319(3) 0.2043(12) Uani 1 1 d . . .
Cl3 Cl 0.68267(15) 0.46831(14) 0.1707(2) 0.1845(10) Uani 1 1 d . . .
O1 O 1.01456(14) 0.31627(11) 0.31667(19) 0.0384(6) Uani 1 1 d . . .
O2 O 0.89808(14) 0.31713(11) 0.2223(2) 0.0390(6) Uani 1 1 d . . .
O3 O 1.09004(14) 0.31740(11) 0.0898(2) 0.0385(6) Uani 1 1 d . . .
O4 O 0.97316(13) 0.31561(11) -0.0025(2) 0.0381(6) Uani 1 1 d . . .
O5 O 0.8138(2) 0.2500 0.0111(3) 0.0528(10) Uani 1 2 d S . .
C1 C 0.9444(2) 0.33635(17) 0.3033(3) 0.0374(9) Uani 1 1 d . . .
C2 C 0.9146(2) 0.38706(19) 0.3870(4) 0.0457(10) Uani 1 1 d . . .
C3 C 0.8995(3) 0.4443(2) 0.3095(4) 0.0659(13) Uani 1 1 d . . .
H3A H 0.9482 0.4576 0.2740 0.099 Uiso 1 1 calc R . .
H3B H 0.8786 0.4769 0.3582 0.099 Uiso 1 1 calc R . .
H3C H 0.8623 0.4343 0.2479 0.099 Uiso 1 1 calc R . .
C4 C 0.9764(2) 0.4020(2) 0.4823(4) 0.0589(12) Uani 1 1 d . . .
H4A H 0.9855 0.3662 0.5307 0.088 Uiso 1 1 calc R . .
H4B H 0.9576 0.4352 0.5315 0.088 Uiso 1 1 calc R . .
H4C H 1.0248 0.4141 0.4444 0.088 Uiso 1 1 calc R . .
C5 C 0.8364(2) 0.36556(18) 0.4448(4) 0.0482(10) Uani 1 1 d . . .
H5A H 0.8178 0.3978 0.4977 0.058 Uiso 1 1 calc R . .
H5B H 0.7973 0.3603 0.3825 0.058 Uiso 1 1 calc R . .
C6 C 0.8320(3) 0.2500 0.4568(5) 0.0454(14) Uani 1 2 d S . .
H6A H 0.8175 0.2500 0.3768 0.054 Uiso 1 2 calc SR . .
C7 C 0.8424(2) 0.30620(19) 0.5145(3) 0.0443(10) Uani 1 1 d . . .
C8 C 0.8605(2) 0.3050(2) 0.6364(4) 0.0572(12) Uani 1 1 d . . .
H8A H 0.8663 0.3419 0.6776 0.069 Uiso 1 1 calc R . .
C9 C 0.8699(4) 0.2500 0.6960(5) 0.0629(19) Uani 1 2 d S . .
H9A H 0.8825 0.2500 0.7767 0.075 Uiso 1 2 calc SR . .
C10 C 1.0433(2) 0.33649(17) 0.0090(3) 0.0387(9) Uani 1 1 d . . .
C11 C 1.0715(2) 0.38745(18) -0.0731(4) 0.0445(10) Uani 1 1 d . . .
C12 C 1.0071(2) 0.4034(2) -0.1642(4) 0.0575(11) Uani 1 1 d . . .
H12A H 0.9604 0.4165 -0.1230 0.086 Uiso 1 1 calc R . .
H12B H 0.9954 0.3676 -0.2114 0.086 Uiso 1 1 calc R . .
H12C H 1.0254 0.4360 -0.2151 0.086 Uiso 1 1 calc R . .
C13 C 1.0915(3) 0.44371(19) 0.0038(4) 0.0663(13) Uani 1 1 d . . .
H13A H 1.0448 0.4576 0.0441 0.099 Uiso 1 1 calc R . .
H13B H 1.1114 0.4762 -0.0460 0.099 Uiso 1 1 calc R . .
H13C H 1.1308 0.4326 0.0616 0.099 Uiso 1 1 calc R . .
C14 C 1.1479(2) 0.36571(19) -0.1381(4) 0.0521(11) Uani 1 1 d . . .
H14A H 1.1644 0.3979 -0.1928 0.063 Uiso 1 1 calc R . .
H14B H 1.1894 0.3606 -0.0793 0.063 Uiso 1 1 calc R . .
C15 C 1.1394(2) 0.3063(2) -0.2065(4) 0.0498(11) Uani 1 1 d . . .
C16 C 1.1513(3) 0.2500 -0.1502(5) 0.0463(14) Uani 1 2 d S . .
H16A H 1.1679 0.2500 -0.0712 0.056 Uiso 1 2 calc SR . .
C17 C 1.1196(3) 0.3049(2) -0.3277(4) 0.0652(13) Uani 1 1 d . . .
H17A H 1.1135 0.3418 -0.3690 0.078 Uiso 1 1 calc R . .
C18 C 1.1091(4) 0.2500 -0.3864(6) 0.075(2) Uani 1 2 d S . .
H18A H 1.0947 0.2500 -0.4664 0.090 Uiso 1 2 calc SR . .
C19 C 0.7134(5) 0.4008(3) 0.0957(8) 0.168(4) Uani 1 1 d . . .
H19A H 0.7484 0.3772 0.1469 0.201 Uiso 1 1 calc R . .
H19B H 0.6678 0.3754 0.0777 0.201 Uiso 1 1 calc R . .
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Ru1 O3 92.12(14) 7_565 . ?
O3 Ru1 O1 89.00(10) 7_565 7_565 ?
O3 Ru1 O1 177.36(10) . 7_565 ?
O3 Ru1 O1 177.36(10) 7_565 . ?
O3 Ru1 O1 89.00(10) . . ?
O1 Ru1 O1 89.77(14) 7_565 . ?
O3 Ru1 Ru2 88.41(7) 7_565 . ?
O3 Ru1 Ru2 88.41(7) . . ?
O1 Ru1 Ru2 89.23(7) 7_565 . ?
O1 Ru1 Ru2 89.23(7) . . ?
O3 Ru1 Cl1 89.95(7) 7_565 . ?
O3 Ru1 Cl1 89.95(7) . . ?
O1 Ru1 Cl1 92.44(7) 7_565 . ?
O1 Ru1 Cl1 92.44(7) . . ?
Ru2 Ru1 Cl1 177.64(4) . . ?
O4 Ru2 O4 90.03(14) . 7_565 ?
O4 Ru2 O2 179.00(10) . 7_565 ?
O4 Ru2 O2 88.97(10) 7_565 7_565 ?
O4 Ru2 O2 88.97(10) . . ?
O4 Ru2 O2 179.00(10) 7_565 . ?
O2 Ru2 O2 92.03(14) 7_565 . ?
O4 Ru2 Ru1 90.38(7) . . ?
O4 Ru2 Ru1 90.38(7) 7_565 . ?
O2 Ru2 Ru1 89.68(7) 7_565 . ?
O2 Ru2 Ru1 89.68(7) . . ?
O4 Ru2 O5 88.78(9) . . ?
O4 Ru2 O5 88.78(9) 7_565 . ?
O2 Ru2 O5 91.14(9) 7_565 . ?
O2 Ru2 O5 91.14(9) . . ?
Ru1 Ru2 O5 178.81(9) . . ?
C1 O1 Ru1 118.7(2) . . ?
C1 O2 Ru2 119.0(2) . . ?
C10 O3 Ru1 120.0(2) . . ?
C10 O4 Ru2 118.8(2) . . ?
O2 C1 O1 123.3(3) . . ?
O2 C1 C2 118.0(3) . . ?
O1 C1 C2 118.7(3) . . ?
C4 C2 C1 110.7(3) . . ?
C4 C2 C3 109.7(4) . . ?
C1 C2 C3 106.7(3) . . ?
C4 C2 C5 110.9(3) . . ?
C1 C2 C5 108.9(3) . . ?
C3 C2 C5 109.8(3) . . ?
C7 C5 C2 114.7(3) . . ?
C7 C6 C7 122.3(5) . 7_565 ?
C6 C7 C8 117.7(4) . . ?
C6 C7 C5 119.8(4) . . ?
C8 C7 C5 122.4(4) . . ?
C9 C8 C7 121.1(5) . . ?
C8 C9 C8 120.0(6) . 7_565 ?
O3 C10 O4 122.3(3) . . ?
O3 C10 C11 118.3(3) . . ?
O4 C10 C11 119.3(3) . . ?
C10 C11 C13 107.9(3) . . ?
C10 C11 C12 110.1(3) . . ?
C13 C11 C12 110.7(3) . . ?
C10 C11 C14 109.0(3) . . ?
C13 C11 C14 108.7(3) . . ?
C12 C11 C14 110.3(3) . . ?
C15 C14 C11 114.7(3) . . ?
C16 C15 C17 117.2(5) . . ?
C16 C15 C14 120.4(4) . . ?
C17 C15 C14 122.4(4) . . ?
C15 C16 C15 123.0(6) 7_565 . ?
C18 C17 C15 121.0(5) . . ?
C17 C18 C17 120.4(7) . 7_565 ?
Cl2 C19 Cl3 110.5(4) . . ?
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
Ru1 O3 2.028(2) 7_565 ?
Ru1 O3 2.028(2) . ?
Ru1 O1 2.034(2) 7_565 ?
Ru1 O1 2.034(2) . ?
Ru1 Ru2 2.2768(6) . ?
Ru1 Cl1 2.4852(14) . ?
Ru2 O4 2.009(2) . ?
Ru2 O4 2.009(2) 7_565 ?
Ru2 O2 2.021(2) 7_565 ?
Ru2 O2 2.021(2) . ?
Ru2 O5 2.342(3) . ?
Cl2 C19 1.687(9) . ?
Cl3 C19 1.766(8) . ?
O1 C1 1.273(4) . ?
O2 C1 1.271(4) . ?
O3 C10 1.272(4) . ?
O4 C10 1.278(4) . ?
C1 C2 1.531(5) . ?
C2 C4 1.531(5) . ?
C2 C3 1.536(5) . ?
C2 C5 1.545(5) . ?
C5 C7 1.508(5) . ?
C6 C7 1.390(5) . ?
C6 C7 1.390(5) 7_565 ?
C7 C8 1.401(5) . ?
C8 C9 1.375(5) . ?
C9 C8 1.375(5) 7_565 ?
C10 C11 1.514(5) . ?
C11 C13 1.531(5) . ?
C11 C12 1.533(5) . ?
C11 C14 1.557(5) . ?
C14 C15 1.505(6) . ?
C15 C16 1.388(5) . ?
C15 C17 1.400(6) . ?
C16 C15 1.388(5) 7_565 ?
C17 C18 1.371(5) . ?
C18 C17 1.371(5) 7_565 ?
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
O3 Ru1 Ru2 O4 -91.10(10) 7_565 . . . ?
O3 Ru1 Ru2 O4 1.06(10) . . . . ?
O1 Ru1 Ru2 O4 179.88(10) 7_565 . . . ?
O1 Ru1 Ru2 O4 90.09(10) . . . . ?
Cl1 Ru1 Ru2 O4 -45.02(7) . . . . ?
O3 Ru1 Ru2 O4 -1.06(10) 7_565 . . 7_565 ?
O3 Ru1 Ru2 O4 91.10(10) . . . 7_565 ?
O1 Ru1 Ru2 O4 -90.09(10) 7_565 . . 7_565 ?
O1 Ru1 Ru2 O4 -179.88(10) . . . 7_565 ?
Cl1 Ru1 Ru2 O4 45.02(7) . . . 7_565 ?
O3 Ru1 Ru2 O2 87.90(10) 7_565 . . 7_565 ?
O3 Ru1 Ru2 O2 -179.94(9) . . . 7_565 ?
O1 Ru1 Ru2 O2 -1.13(10) 7_565 . . 7_565 ?
O1 Ru1 Ru2 O2 -90.91(9) . . . 7_565 ?
Cl1 Ru1 Ru2 O2 133.98(7) . . . 7_565 ?
O3 Ru1 Ru2 O2 179.94(9) 7_565 . . . ?
O3 Ru1 Ru2 O2 -87.90(10) . . . . ?
O1 Ru1 Ru2 O2 90.91(9) 7_565 . . . ?
O1 Ru1 Ru2 O2 1.13(10) . . . . ?
Cl1 Ru1 Ru2 O2 -133.98(7) . . . . ?
O3 Ru1 Ru2 O5 -46.08(7) 7_565 . . . ?
O3 Ru1 Ru2 O5 46.08(7) . . . . ?
O1 Ru1 Ru2 O5 -135.11(7) 7_565 . . . ?
O1 Ru1 Ru2 O5 135.11(7) . . . . ?
Cl1 Ru1 Ru2 O5 0.001(2) . . . . ?
O3 Ru1 O1 C1 -28(2) 7_565 . . . ?
O3 Ru1 O1 C1 87.5(3) . . . . ?
O1 Ru1 O1 C1 -90.2(3) 7_565 . . . ?
Ru2 Ru1 O1 C1 -1.0(2) . . . . ?
Cl1 Ru1 O1 C1 177.4(2) . . . . ?
O4 Ru2 O2 C1 -92.1(3) . . . . ?
O4 Ru2 O2 C1 -95(6) 7_565 . . . ?
O2 Ru2 O2 C1 88.0(3) 7_565 . . . ?
Ru1 Ru2 O2 C1 -1.7(2) . . . . ?
O5 Ru2 O2 C1 179.1(2) . . . . ?
O3 Ru1 O3 C10 86.6(3) 7_565 . . . ?
O1 Ru1 O3 C10 -28(2) 7_565 . . . ?
O1 Ru1 O3 C10 -91.0(3) . . . . ?
Ru2 Ru1 O3 C10 -1.7(2) . . . . ?
Cl1 Ru1 O3 C10 176.6(2) . . . . ?
O4 Ru2 O4 C10 -91.2(3) 7_565 . . . ?
O2 Ru2 O4 C10 -94(6) 7_565 . . . ?
O2 Ru2 O4 C10 88.9(3) . . . . ?
Ru1 Ru2 O4 C10 -0.8(2) . . . . ?
O5 Ru2 O4 C10 -180.0(3) . . . . ?
Ru2 O2 C1 O1 1.4(5) . . . . ?
Ru2 O2 C1 C2 -179.8(2) . . . . ?
Ru1 O1 C1 O2 -0.1(5) . . . . ?
Ru1 O1 C1 C2 -178.9(2) . . . . ?
O2 C1 C2 C4 177.1(3) . . . . ?
O1 C1 C2 C4 -4.0(5) . . . . ?
O2 C1 C2 C3 -63.5(4) . . . . ?
O1 C1 C2 C3 115.3(4) . . . . ?
O2 C1 C2 C5 54.9(4) . . . . ?
O1 C1 C2 C5 -126.2(4) . . . . ?
C4 C2 C5 C7 -63.7(4) . . . . ?
C1 C2 C5 C7 58.4(4) . . . . ?
C3 C2 C5 C7 174.9(3) . . . . ?
C7 C6 C7 C8 -2.9(7) 7_565 . . . ?
C7 C6 C7 C5 175.2(3) 7_565 . . . ?
C2 C5 C7 C6 -87.8(5) . . . . ?
C2 C5 C7 C8 90.2(4) . . . . ?
C6 C7 C8 C9 1.8(6) . . . . ?
C5 C7 C8 C9 -176.3(4) . . . . ?
C7 C8 C9 C8 -0.8(9) . . . 7_565 ?
Ru1 O3 C10 O4 1.6(5) . . . . ?
Ru1 O3 C10 C11 179.2(2) . . . . ?
Ru2 O4 C10 O3 -0.3(5) . . . . ?
Ru2 O4 C10 C11 -178.0(2) . . . . ?
O3 C10 C11 C13 -59.4(4) . . . . ?
O4 C10 C11 C13 118.3(4) . . . . ?
O3 C10 C11 C12 179.6(3) . . . . ?
O4 C10 C11 C12 -2.6(5) . . . . ?
O3 C10 C11 C14 58.5(4) . . . . ?
O4 C10 C11 C14 -123.8(4) . . . . ?
C10 C11 C14 C15 56.1(4) . . . . ?
C13 C11 C14 C15 173.5(3) . . . . ?
C12 C11 C14 C15 -65.0(4) . . . . ?
C11 C14 C15 C16 -87.2(5) . . . . ?
C11 C14 C15 C17 92.9(5) . . . . ?
C17 C15 C16 C15 -4.3(8) . . . 7_565 ?
C14 C15 C16 C15 175.8(3) . . . 7_565 ?
C16 C15 C17 C18 2.8(7) . . . . ?
C14 C15 C17 C18 -177.3(5) . . . . ?
C15 C17 C18 C17 -1.5(10) . . . 7_565 ?
