#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/52/2225211.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2225211
loop_
_publ_author_name
'Harrad, Mohamed Anouar'
'Valerga, Pedro'
'Puerta, M. Carmen'
'Ali, Mustapha Ait'
'El Firdoussi, Larbi'
'Karim, Abdellah'
_publ_section_title
'[(1R)-3-Benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-onato-κ²O,O']chlorido(η⁶-p-cymene)ruthenium(II)'
_journal_coeditor_code           CV2696
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m281
_journal_paper_doi               10.1107/S1600536810005015
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Ru Cl (C10 H14) (C17 H19 O2)]'
_chemical_formula_moiety         'C27 H33 Cl O2 Ru'
_chemical_formula_sum            'C27 H33 Cl O2 Ru'
_chemical_formula_weight         526.05
_chemical_name_systematic
'[(1R)-3-Benzoyl-1,7,7-trimethylbicyclo[2.2.1]heptan-2-onato-κ²O,O']chlorido(η⁶-p-cymene)ruthenium(II)'
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_cell_angle_alpha                108.13(3)
_cell_angle_beta                 97.62(3)
_cell_angle_gamma                102.54(3)
_cell_formula_units_Z            2
_cell_length_a                   9.833(2)
_cell_length_b                   10.572(2)
_cell_length_c                   12.785(3)
_cell_measurement_reflns_used    7193
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.560
_cell_measurement_theta_min      2.461
_cell_volume                     1203.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       '1700 omega scan frames, 0.3 deg, 10 sec'
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10110
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        -0.0017
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.951
_refine_diff_density_min         -1.339
_refine_ls_abs_structure_details 'Flack (1983), 2564 Friedel pairs'
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     547
_refine_ls_number_reflns         7861
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0312
_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)+(0.0375P)²+2.2953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                7619
_reflns_number_total             7861
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2696.cif
_cod_data_source_block           I
_cod_database_code               2225211
_cod_database_fobs_code          2225211
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru Ru1 0.14364(3) 0.83889(3) 0.44793(2) 0.01034(11) Uani d . 1 . .
Cl Cl1 0.3688(2) 0.7926(2) 0.49401(15) 0.0171(4) Uani d . 1 . .
O O1 0.0772(6) 0.7426(6) 0.5592(4) 0.0124(11) Uani d . 1 . .
O O2 0.0867(6) 0.6470(5) 0.3196(4) 0.0165(12) Uani d . 1 . .
C C1 -0.0099(9) 0.9619(9) 0.4831(7) 0.0163(12) Uani d . 1 . .
C C2 -0.0163(10) 0.9068(9) 0.3639(6) 0.0167(11) Uani d . 1 . .
H H2 -0.1058 0.8554 0.3142 0.020 Uiso calc R 1 . .
C C3 0.1045(9) 0.9267(8) 0.3198(6) 0.0167(11) Uani d . 1 . .
H H3 0.0959 0.8882 0.2407 0.020 Uiso calc R 1 . .
C C4 0.2426(9) 1.0043(9) 0.3907(7) 0.0163(12) Uani d . 1 . .
C C5 0.2486(9) 1.0584(8) 0.5096(7) 0.0169(13) Uani d . 1 . .
H H5 0.3381 1.1089 0.5596 0.020 Uiso calc R 1 . .
C C6 0.1293(8) 1.0392(8) 0.5525(6) 0.0123(12) Uani d . 1 . .
H H6 0.1383 1.0785 0.6316 0.015 Uiso calc R 1 . .
C C7 -0.1356(8) 0.9335(9) 0.5332(7) 0.0178(17) Uani d . 1 . .
H H7 -0.1003 0.9336 0.6103 0.021 Uiso calc R 1 . .
C C8 -0.2081(11) 1.0542(10) 0.5469(9) 0.033(2) Uani d . 1 . .
H H8A -0.2423 1.0576 0.4725 0.050 Uiso calc R 1 . .
H H8B -0.1386 1.1423 0.5936 0.050 Uiso calc R 1 . .
H H8C -0.2889 1.0382 0.5830 0.050 Uiso calc R 1 . .
C C9 -0.2507(9) 0.7956(9) 0.4684(8) 0.0239(18) Uani d . 1 . .
H H9A -0.3281 0.7874 0.5089 0.036 Uiso calc R 1 . .
H H9B -0.2084 0.7184 0.4623 0.036 Uiso calc R 1 . .
H H9C -0.2886 0.7933 0.3928 0.036 Uiso calc R 1 . .
C C10 0.3731(9) 1.0207(9) 0.3443(8) 0.0237(18) Uani d . 1 . .
H H10A 0.4118 1.1182 0.3540 0.036 Uiso calc R 1 . .
H H10B 0.3495 0.9643 0.2640 0.036 Uiso calc R 1 . .
H H10C 0.4443 0.9904 0.3844 0.036 Uiso calc R 1 . .
C C11 0.0264(8) 0.6110(8) 0.5354(6) 0.0142(15) Uani d . 1 . .
C C12 -0.0215(8) 0.5737(8) 0.6320(6) 0.0155(15) Uani d . 1 . .
C C13 0.0235(8) 0.4731(8) 0.6649(6) 0.0174(15) Uani d . 1 . .
H H13 0.0810 0.4240 0.6236 0.021 Uiso calc R 1 . .
C C14 -0.0142(8) 0.4439(8) 0.7564(6) 0.0240(16) Uani d . 1 . .
H H14 0.0166 0.3749 0.7783 0.029 Uiso calc R 1 . .
C C15 -0.0977(8) 0.5162(8) 0.8164(6) 0.0216(15) Uani d . 1 . .
H H15 -0.1226 0.4974 0.8804 0.026 Uiso calc R 1 . .
C C16 -0.1451(9) 0.6153(9) 0.7845(6) 0.0241(17) Uani d . 1 . .
H H16 -0.2046 0.6623 0.8248 0.029 Uiso calc R 1 . .
C C17 -0.1043(8) 0.6456(8) 0.6919(6) 0.0152(15) Uani d . 1 . .
H H17 -0.1338 0.7156 0.6706 0.018 Uiso calc R 1 . .
C C18 0.0064(8) 0.5095(8) 0.4311(6) 0.0140(14) Uani d . 1 . .
C C19 0.0341(8) 0.5356(8) 0.3317(6) 0.0126(14) Uani d . 1 . .
C C20 -0.0353(6) 0.4018(5) 0.2333(4) 0.0164(10) Uani d . 1 . .
C C21 -0.0127(6) 0.2937(5) 0.2883(4) 0.0183(10) Uani d . 1 . .
C C22 -0.0807(6) 0.3561(5) 0.3890(4) 0.0172(10) Uani d . 1 . .
H H22 -0.0800 0.3109 0.4471 0.021 Uiso calc R 1 . .
C C23 -0.2285(6) 0.3514(5) 0.3298(4) 0.0192(10) Uani d . 1 . .
H H23A -0.2683 0.4205 0.3786 0.023 Uiso calc R 1 . .
H H23B -0.2957 0.2583 0.3075 0.023 Uiso calc R 1 . .
C C24 -0.1973(5) 0.3875(5) 0.2251(4) 0.0175(10) Uani d . 1 . .
H H24A -0.2192 0.4753 0.2274 0.021 Uiso calc R 1 . .
H H24B -0.2542 0.3129 0.1546 0.021 Uiso calc R 1 . .
C C25 0.0181(9) 0.3967(9) 0.1269(6) 0.0229(18) Uani d . 1 . .
H H25A 0.0018 0.4739 0.1048 0.034 Uiso calc R 1 . .
H H25B -0.0334 0.3090 0.0664 0.034 Uiso calc R 1 . .
H H25C 0.1204 0.4039 0.1405 0.034 Uiso calc R 1 . .
C C26 -0.0953(9) 0.1438(8) 0.2157(7) 0.0236(17) Uani d . 1 . .
H H26A -0.0790 0.0823 0.2569 0.035 Uiso calc R 1 . .
H H26B -0.0620 0.1168 0.1452 0.035 Uiso calc R 1 . .
H H26C -0.1974 0.1366 0.1989 0.035 Uiso calc R 1 . .
C C27 0.1446(6) 0.3002(6) 0.3233(5) 0.0255(12) Uani d . 1 . .
H H27A 0.1989 0.3960 0.3676 0.038 Uiso calc R 1 . .
H H27B 0.1824 0.2670 0.2558 0.038 Uiso calc R 1 . .
H H27C 0.1529 0.2417 0.3688 0.038 Uiso calc R 1 . .
Ru Ru2 0.32581(3) 0.12766(3) 0.89620(2) 0.00965(11) Uani d . 1 . .
Cl Cl2 0.1007(2) 0.1732(2) 0.84692(15) 0.0175(4) Uani d . 1 . .
O O3 0.3958(6) 0.2229(5) 0.7863(4) 0.0128(11) Uani d . 1 . .
O O4 0.3740(6) 0.3211(6) 1.0232(4) 0.0120(11) Uani d . 1 . .
C C28 0.4792(8) 0.0063(8) 0.8589(6) 0.0120(10) Uani d . 1 . .
C C29 0.4905(9) 0.0603(8) 0.9753(6) 0.0140(12) Uani d . 1 . .
H H29 0.5809 0.1113 1.0237 0.017 Uiso calc R 1 . .
C C30 0.3639(8) 0.0387(8) 1.0228(6) 0.0134(12) Uani d . 1 . .
H H30 0.3733 0.0777 1.1020 0.016 Uiso calc R 1 . .
C C31 0.2307(8) -0.0369(8) 0.9555(6) 0.0120(10) Uani d . 1 . .
C C32 0.2195(8) -0.0920(8) 0.8365(6) 0.0127(11) Uani d . 1 . .
H H32 0.1285 -0.1421 0.7887 0.015 Uiso calc R 1 . .
C C33 0.3411(9) -0.0737(8) 0.7879(6) 0.0127(11) Uani d . 1 . .
H H33 0.3314 -0.1141 0.7088 0.015 Uiso calc R 1 . .
C C34 0.6049(8) 0.0281(9) 0.8037(7) 0.0173(16) Uani d . 1 . .
H H34 0.5684 0.0286 0.7271 0.021 Uiso calc R 1 . .
C C35 0.7144(10) 0.1657(10) 0.8690(8) 0.030(2) Uani d . 1 . .
H H35A 0.6654 0.2367 0.8971 0.045 Uiso calc R 1 . .
H H35B 0.7740 0.1919 0.8194 0.045 Uiso calc R 1 . .
H H35C 0.7745 0.1574 0.9328 0.045 Uiso calc R 1 . .
C C36 0.6654(10) -0.0953(11) 0.7886(8) 0.030(2) Uani d . 1 . .
H H36A 0.6936 -0.1035 0.8621 0.046 Uiso calc R 1 . .
H H36B 0.7489 -0.0823 0.7549 0.046 Uiso calc R 1 . .
H H36C 0.5927 -0.1797 0.7390 0.046 Uiso calc R 1 . .
C C37 0.0993(10) -0.0538(10) 1.0041(7) 0.027(2) Uani d . 1 . .
H H37A 0.0776 -0.1431 1.0152 0.040 Uiso calc R 1 . .
H H37B 0.0186 -0.0505 0.9520 0.040 Uiso calc R 1 . .
H H37C 0.1162 0.0211 1.0766 0.040 Uiso calc R 1 . .
C C38 0.4313(8) 0.3543(8) 0.8048(6) 0.0110(14) Uani d . 1 . .
C C39 0.4676(8) 0.3908(8) 0.7070(6) 0.0116(13) Uani d . 1 . .
C C40 0.5570(8) 0.3281(8) 0.6450(6) 0.0164(15) Uani d . 1 . .
H H40 0.5960 0.2631 0.6669 0.020 Uiso calc R 1 . .
C C41 0.5898(8) 0.3590(8) 0.5526(6) 0.0195(15) Uani d . 1 . .
H H41 0.6546 0.3190 0.5136 0.023 Uiso calc R 1 . .
C C42 0.5275(9) 0.4492(9) 0.5163(6) 0.031(2) Uani d . 1 . .
H H42 0.5463 0.4670 0.4505 0.037 Uiso calc R 1 . .
C C43 0.4391(8) 0.5120(7) 0.5758(6) 0.0229(16) Uani d . 1 . .
H H43 0.3980 0.5742 0.5513 0.028 Uiso calc R 1 . .
C C44 0.4092(8) 0.4853(8) 0.6722(6) 0.0178(15) Uani d . 1 . .
H H44 0.3497 0.5308 0.7139 0.021 Uiso calc R 1 . .
C C45 0.4363(8) 0.4568(8) 0.9050(6) 0.0129(13) Uani d . 1 . .
C C46 0.4133(8) 0.4318(7) 1.0041(6) 0.0145(15) Uani d . 1 . .
C C47 0.4402(6) 0.5739(5) 1.0964(4) 0.0146(10) Uani d . 1 . .
C C48 0.3087(6) 0.6237(5) 1.0558(4) 0.0187(10) Uani d . 1 . .
H H48A 0.2185 0.5495 1.0360 0.022 Uiso calc R 1 . .
H H48B 0.3013 0.7066 1.1153 0.022 Uiso calc R 1 . .
C C49 0.3407(6) 0.6578(5) 0.9512(4) 0.0197(10) Uani d . 1 . .
H H49A 0.3569 0.7579 0.9648 0.024 Uiso calc R 1 . .
H H49B 0.2622 0.6045 0.8844 0.024 Uiso calc R 1 . .
C C50 0.4792(6) 0.6123(5) 0.9367(4) 0.0146(10) Uani d . 1 . .
H H50 0.5329 0.6475 0.8856 0.018 Uiso calc R 1 . .
C C51 0.5615(6) 0.6616(5) 1.0609(4) 0.0139(9) Uani d . 1 . .
C C52 0.4574(9) 0.5748(9) 1.2163(6) 0.0194(17) Uani d . 1 . .
H H52A 0.5369 0.5370 1.2330 0.029 Uiso calc R 1 . .
H H52B 0.3694 0.5180 1.2247 0.029 Uiso calc R 1 . .
H H52C 0.4771 0.6700 1.2687 0.029 Uiso calc R 1 . .
C C53 0.5972(8) 0.8174(8) 1.1258(6) 0.0191(15) Uani d . 1 . .
H H53A 0.6490 0.8386 1.2028 0.029 Uiso calc R 1 . .
H H53B 0.5087 0.8456 1.1281 0.029 Uiso calc R 1 . .
H H53C 0.6566 0.8678 1.0879 0.029 Uiso calc R 1 . .
C C54 0.7017(6) 0.6204(5) 1.0730(5) 0.0189(10) Uani d . 1 . .
H H54A 0.6832 0.5210 1.0321 0.028 Uiso calc R 1 . .
H H54B 0.7414 0.6415 1.1529 0.028 Uiso calc R 1 . .
H H54C 0.7700 0.6724 1.0417 0.028 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Ru1 O1 . . 89.7(2) ?
O2 Ru1 C3 . . 87.5(3) ?
O1 Ru1 C3 . . 152.5(3) ?
O2 Ru1 C2 . . 91.9(3) ?
O1 Ru1 C2 . . 115.4(3) ?
C3 Ru1 C2 . . 37.5(3) ?
O2 Ru1 C5 . . 149.6(3) ?
O1 Ru1 C5 . . 120.1(3) ?
C3 Ru1 C5 . . 68.9(3) ?
C2 Ru1 C5 . . 80.9(3) ?
O2 Ru1 C6 . . 159.5(2) ?
O1 Ru1 C6 . . 93.3(2) ?
C3 Ru1 C6 . . 80.5(3) ?
C2 Ru1 C6 . . 68.5(3) ?
C5 Ru1 C6 . . 36.7(3) ?
O2 Ru1 C4 . . 111.4(3) ?
O1 Ru1 C4 . . 158.6(2) ?
C3 Ru1 C4 . . 38.7(3) ?
C2 Ru1 C4 . . 69.0(3) ?
C5 Ru1 C4 . . 38.5(3) ?
C6 Ru1 C4 . . 68.2(3) ?
O2 Ru1 C1 . . 121.5(3) ?
O1 Ru1 C1 . . 89.5(3) ?
C3 Ru1 C1 . . 69.0(3) ?
C2 Ru1 C1 . . 38.5(3) ?
C5 Ru1 C1 . . 68.6(3) ?
C6 Ru1 C1 . . 38.4(3) ?
C4 Ru1 C1 . . 82.6(3) ?
O2 Ru1 Cl1 . . 85.99(17) ?
O1 Ru1 Cl1 . . 86.05(15) ?
C3 Ru1 Cl1 . . 121.0(2) ?
C2 Ru1 Cl1 . . 158.5(2) ?
C5 Ru1 Cl1 . . 90.1(2) ?
C6 Ru1 Cl1 . . 114.4(2) ?
C4 Ru1 Cl1 . . 91.8(2) ?
C1 Ru1 Cl1 . . 152.2(2) ?
C11 O1 Ru1 . . 126.1(5) ?
C19 O2 Ru1 . . 124.1(5) ?
C6 C1 C2 . . 115.7(7) ?
C6 C1 C7 . . 121.4(7) ?
C2 C1 C7 . . 122.8(8) ?
C6 C1 Ru1 . . 69.7(4) ?
C2 C1 Ru1 . . 69.2(4) ?
C7 C1 Ru1 . . 127.8(5) ?
C3 C2 C1 . . 121.7(8) ?
C3 C2 Ru1 . . 70.9(4) ?
C1 C2 Ru1 . . 72.2(4) ?
C3 C2 H2 . . 119.1 ?
C1 C2 H2 . . 119.1 ?
Ru1 C2 H2 . . 130.4 ?
C2 C3 C4 . . 121.7(7) ?
C2 C3 Ru1 . . 71.6(4) ?
C4 C3 Ru1 . . 72.0(4) ?
C2 C3 H3 . . 119.2 ?
C4 C3 H3 . . 119.2 ?
Ru1 C3 H3 . . 129.8 ?
C3 C4 C5 . . 116.4(7) ?
C3 C4 C10 . . 121.8(8) ?
C5 C4 C10 . . 121.7(8) ?
C3 C4 Ru1 . . 69.3(5) ?
C5 C4 Ru1 . . 69.8(4) ?
C10 C4 Ru1 . . 128.6(6) ?
C6 C5 C4 . . 121.7(8) ?
C6 C5 Ru1 . . 71.9(5) ?
C4 C5 Ru1 . . 71.7(5) ?
C6 C5 H5 . . 119.2 ?
C4 C5 H5 . . 119.2 ?
Ru1 C5 H5 . . 129.8 ?
C5 C6 C1 . . 122.8(7) ?
C5 C6 Ru1 . . 71.4(5) ?
C1 C6 Ru1 . . 71.9(4) ?
C5 C6 H6 . . 118.6 ?
C1 C6 H6 . . 118.6 ?
Ru1 C6 H6 . . 131.1 ?
C1 C7 C9 . . 116.4(7) ?
C1 C7 C8 . . 109.0(7) ?
C9 C7 C8 . . 108.2(7) ?
C1 C7 H7 . . 107.7 ?
C9 C7 H7 . . 107.7 ?
C8 C7 H7 . . 107.7 ?
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 ?
C4 C10 H10A . . 109.5 ?
C4 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C4 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O1 C11 C18 . . 125.8(7) ?
O1 C11 C12 . . 113.7(7) ?
C18 C11 C12 . . 120.4(7) ?
C17 C12 C13 . . 119.8(7) ?
C17 C12 C11 . . 119.4(7) ?
C13 C12 C11 . . 120.7(7) ?
C14 C13 C12 . . 120.8(7) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C15 . . 119.3(7) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C16 C15 C14 . . 120.9(7) ?
C16 C15 H15 . . 119.5 ?
C14 C15 H15 . . 119.5 ?
C15 C16 C17 . . 119.3(8) ?
C15 C16 H16 . . 120.4 ?
C17 C16 H16 . . 120.4 ?
C12 C17 C16 . . 119.9(7) ?
C12 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C11 C18 C19 . . 124.6(7) ?
C11 C18 C22 . . 128.8(7) ?
C19 C18 C22 . . 105.0(6) ?
O2 C19 C18 . . 129.6(7) ?
O2 C19 C20 . . 122.9(6) ?
C18 C19 C20 . . 106.8(6) ?
C25 C20 C19 . . 113.9(5) ?
C25 C20 C24 . . 116.1(5) ?
C19 C20 C24 . . 103.3(4) ?
C25 C20 C21 . . 118.6(5) ?
C19 C20 C21 . . 100.8(4) ?
C24 C20 C21 . . 101.8(4) ?
C27 C21 C26 . . 108.7(5) ?
C27 C21 C20 . . 113.4(5) ?
C26 C21 C20 . . 114.1(5) ?
C27 C21 C22 . . 113.9(4) ?
C26 C21 C22 . . 112.8(5) ?
C20 C21 C22 . . 93.4(4) ?
C23 C22 C18 . . 105.5(4) ?
C23 C22 C21 . . 102.6(4) ?
C18 C22 C21 . . 100.6(4) ?
C23 C22 H22 . . 115.4 ?
C18 C22 H22 . . 115.4 ?
C21 C22 H22 . . 115.4 ?
C22 C23 C24 . . 102.5(4) ?
C22 C23 H23A . . 111.3 ?
C24 C23 H23A . . 111.3 ?
C22 C23 H23B . . 111.3 ?
C24 C23 H23B . . 111.3 ?
H23A C23 H23B . . 109.2 ?
C23 C24 C20 . . 104.3(4) ?
C23 C24 H24A . . 110.9 ?
C20 C24 H24A . . 110.9 ?
C23 C24 H24B . . 110.9 ?
C20 C24 H24B . . 110.9 ?
H24A C24 H24B . . 108.9 ?
C20 C25 H25A . . 109.5 ?
C20 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C20 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C21 C26 H26A . . 109.5 ?
C21 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C21 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C21 C27 H27A . . 109.5 ?
C21 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C21 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
O3 Ru2 O4 . . 89.7(2) ?
O3 Ru2 C30 . . 151.5(2) ?
O4 Ru2 C30 . . 89.0(3) ?
O3 Ru2 C29 . . 112.2(3) ?
O4 Ru2 C29 . . 95.0(3) ?
C30 Ru2 C29 . . 39.7(3) ?
O3 Ru2 C32 . . 121.0(2) ?
O4 Ru2 C32 . . 148.3(2) ?
C30 Ru2 C32 . . 68.0(3) ?
C29 Ru2 C32 . . 81.3(3) ?
O3 Ru2 C31 . . 159.2(2) ?
O4 Ru2 C31 . . 110.9(2) ?
C30 Ru2 C31 . . 37.3(3) ?
C29 Ru2 C31 . . 69.8(3) ?
C32 Ru2 C31 . . 38.3(3) ?
O3 Ru2 C28 . . 87.6(2) ?
O4 Ru2 C28 . . 124.1(3) ?
C30 Ru2 C28 . . 69.8(3) ?
C29 Ru2 C28 . . 37.5(3) ?
C32 Ru2 C28 . . 69.4(3) ?
C31 Ru2 C28 . . 82.8(3) ?
O3 Ru2 C33 . . 91.9(3) ?
O4 Ru2 C33 . . 162.2(2) ?
C30 Ru2 C33 . . 81.2(3) ?
C29 Ru2 C33 . . 68.1(3) ?
C32 Ru2 C33 . . 38.1(3) ?
C31 Ru2 C33 . . 69.2(3) ?
C28 Ru2 C33 . . 38.4(3) ?
O3 Ru2 Cl2 . . 86.42(15) ?
O4 Ru2 Cl2 . . 84.06(16) ?
C30 Ru2 Cl2 . . 121.7(2) ?
C29 Ru2 Cl2 . . 161.4(2) ?
C32 Ru2 Cl2 . . 89.8(2) ?
C31 Ru2 Cl2 . . 93.18(19) ?
C28 Ru2 Cl2 . . 151.1(2) ?
C33 Ru2 Cl2 . . 113.7(2) ?
C38 O3 Ru2 . . 126.7(5) ?
C46 O4 Ru2 . . 121.8(5) ?
C29 C28 C33 . . 118.5(7) ?
C29 C28 C34 . . 123.1(7) ?
C33 C28 C34 . . 118.4(7) ?
C29 C28 Ru2 . . 70.1(4) ?
C33 C28 Ru2 . . 71.1(4) ?
C34 C28 Ru2 . . 130.4(5) ?
C28 C29 C30 . . 120.3(7) ?
C28 C29 Ru2 . . 72.4(4) ?
C30 C29 Ru2 . . 69.4(4) ?
C28 C29 H29 . . 119.9 ?
C30 C29 H29 . . 119.9 ?
Ru2 C29 H29 . . 131.0 ?
C31 C30 C29 . . 121.7(7) ?
C31 C30 Ru2 . . 73.1(4) ?
C29 C30 Ru2 . . 70.8(4) ?
C31 C30 H30 . . 119.1 ?
C29 C30 H30 . . 119.1 ?
Ru2 C30 H30 . . 129.4 ?
C30 C31 C32 . . 117.9(7) ?
C30 C31 C37 . . 121.6(7) ?
C32 C31 C37 . . 120.4(7) ?
C30 C31 Ru2 . . 69.6(5) ?
C32 C31 Ru2 . . 70.2(4) ?
C37 C31 Ru2 . . 128.5(5) ?
C33 C32 C31 . . 121.7(7) ?
C33 C32 Ru2 . . 72.1(4) ?
C31 C32 Ru2 . . 71.5(4) ?
C33 C32 H32 . . 119.2 ?
C31 C32 H32 . . 119.2 ?
Ru2 C32 H32 . . 129.8 ?
C32 C33 C28 . . 119.9(7) ?
C32 C33 Ru2 . . 69.8(4) ?
C28 C33 Ru2 . . 70.5(4) ?
C32 C33 H33 . . 120.0 ?
C28 C33 H33 . . 120.0 ?
Ru2 C33 H33 . . 132.6 ?
C28 C34 C36 . . 108.0(7) ?
C28 C34 C35 . . 111.9(7) ?
C36 C34 C35 . . 113.4(7) ?
C28 C34 H34 . . 107.8 ?
C36 C34 H34 . . 107.8 ?
C35 C34 H34 . . 107.8 ?
C34 C35 H35A . . 109.5 ?
C34 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
C34 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C34 C36 H36A . . 109.5 ?
C34 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C34 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C31 C37 H37A . . 109.5 ?
C31 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C31 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
O3 C38 C45 . . 125.3(7) ?
O3 C38 C39 . . 114.3(7) ?
C45 C38 C39 . . 120.5(7) ?
C40 C39 C44 . . 118.6(7) ?
C40 C39 C38 . . 120.4(7) ?
C44 C39 C38 . . 121.0(7) ?
C41 C40 C39 . . 121.1(7) ?
C41 C40 H40 . . 119.4 ?
C39 C40 H40 . . 119.4 ?
C40 C41 C42 . . 119.9(8) ?
C40 C41 H41 . . 120.1 ?
C42 C41 H41 . . 120.1 ?
C43 C42 C41 . . 120.0(7) ?
C43 C42 H42 . . 120.0 ?
C41 C42 H42 . . 120.0 ?
C42 C43 C44 . . 120.6(7) ?
C42 C43 H43 . . 119.7 ?
C44 C43 H43 . . 119.7 ?
C43 C44 C39 . . 119.7(7) ?
C43 C44 H44 . . 120.1 ?
C39 C44 H44 . . 120.1 ?
C38 C45 C46 . . 124.0(7) ?
C38 C45 C50 . . 129.8(6) ?
C46 C45 C50 . . 106.0(6) ?
O4 C46 C45 . . 131.7(7) ?
O4 C46 C47 . . 121.5(6) ?
C45 C46 C47 . . 106.7(6) ?
C52 C47 C46 . . 115.8(5) ?
C52 C47 C51 . . 120.5(5) ?
C46 C47 C51 . . 100.4(4) ?
C52 C47 C48 . . 114.6(5) ?
C46 C47 C48 . . 101.8(4) ?
C51 C47 C48 . . 100.9(4) ?
C49 C48 C47 . . 104.5(4) ?
C49 C48 H48A . . 110.8 ?
C47 C48 H48A . . 110.8 ?
C49 C48 H48B . . 110.8 ?
C47 C48 H48B . . 110.8 ?
H48A C48 H48B . . 108.9 ?
C48 C49 C50 . . 102.0(4) ?
C48 C49 H49A . . 111.4 ?
C50 C49 H49A . . 111.4 ?
C48 C49 H49B . . 111.4 ?
C50 C49 H49B . . 111.4 ?
H49A C49 H49B . . 109.2 ?
C45 C50 C51 . . 102.2(4) ?
C45 C50 C49 . . 105.8(5) ?
C51 C50 C49 . . 101.7(4) ?
C45 C50 H50 . . 115.2 ?
C51 C50 H50 . . 115.2 ?
C49 C50 H50 . . 115.2 ?
C53 C51 C54 . . 107.1(5) ?
C53 C51 C47 . . 113.7(5) ?
C54 C51 C47 . . 113.7(4) ?
C53 C51 C50 . . 115.3(4) ?
C54 C51 C50 . . 113.2(4) ?
C47 C51 C50 . . 93.8(4) ?
C47 C52 H52A . . 109.5 ?
C47 C52 H52B . . 109.5 ?
H52A C52 H52B . . 109.5 ?
C47 C52 H52C . . 109.5 ?
H52A C52 H52C . . 109.5 ?
H52B C52 H52C . . 109.5 ?
C51 C53 H53A . . 109.5 ?
C51 C53 H53B . . 109.5 ?
H53A C53 H53B . . 109.5 ?
C51 C53 H53C . . 109.5 ?
H53A C53 H53C . . 109.5 ?
H53B C53 H53C . . 109.5 ?
C51 C54 H54A . . 109.5 ?
C51 C54 H54B . . 109.5 ?
H54A C54 H54B . . 109.5 ?
C51 C54 H54C . . 109.5 ?
H54A C54 H54C . . 109.5 ?
H54B C54 H54C . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ru1 O2 . 2.077(5) ?
Ru1 O1 . 2.084(5) ?
Ru1 C3 . 2.151(7) ?
Ru1 C2 . 2.160(7) ?
Ru1 C5 . 2.163(8) ?
Ru1 C6 . 2.170(8) ?
Ru1 C4 . 2.188(9) ?
Ru1 C1 . 2.200(8) ?
Ru1 Cl1 . 2.4069(19) ?
O1 C11 . 1.293(10) ?
O2 C19 . 1.246(9) ?
C1 C6 . 1.438(12) ?
C1 C2 . 1.439(10) ?
C1 C7 . 1.483(12) ?
C2 C3 . 1.385(12) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.437(12) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.436(11) ?
C4 C10 . 1.482(11) ?
C5 C6 . 1.363(11) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C9 . 1.541(12) ?
C7 C8 . 1.568(11) ?
C7 H7 . 1.0000 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
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 C18 . 1.384(11) ?
C11 C12 . 1.510(11) ?
C12 C17 . 1.379(11) ?
C12 C13 . 1.392(10) ?
C13 C14 . 1.376(10) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.386(11) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.381(11) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.405(11) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
C18 C19 . 1.429(10) ?
C18 C22 . 1.544(9) ?
C19 C20 . 1.515(9) ?
C20 C25 . 1.512(9) ?
C20 C24 . 1.553(7) ?
C20 C21 . 1.554(7) ?
C21 C27 . 1.533(8) ?
C21 C26 . 1.536(9) ?
C21 C22 . 1.559(7) ?
C22 C23 . 1.530(8) ?
C22 H22 . 1.0000 ?
C23 C24 . 1.551(7) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 H25A . 0.9800 ?
C25 H25B . 0.9800 ?
C25 H25C . 0.9800 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C26 H26C . 0.9800 ?
C27 H27A . 0.9800 ?
C27 H27B . 0.9800 ?
C27 H27C . 0.9800 ?
Ru2 O3 . 2.073(5) ?
Ru2 O4 . 2.086(5) ?
Ru2 C30 . 2.141(7) ?
Ru2 C29 . 2.160(7) ?
Ru2 C32 . 2.168(8) ?
Ru2 C31 . 2.186(8) ?
Ru2 C28 . 2.190(7) ?
Ru2 C33 . 2.198(8) ?
Ru2 Cl2 . 2.4108(18) ?
O3 C38 . 1.293(9) ?
O4 C46 . 1.259(9) ?
C28 C29 . 1.397(10) ?
C28 C33 . 1.442(11) ?
C28 C34 . 1.513(10) ?
C29 C30 . 1.461(11) ?
C29 H29 . 0.9500 ?
C30 C31 . 1.384(11) ?
C30 H30 . 0.9500 ?
C31 C32 . 1.428(10) ?
C31 C37 . 1.506(11) ?
C32 C33 . 1.424(11) ?
C32 H32 . 0.9500 ?
C33 H33 . 0.9500 ?
C34 C36 . 1.517(11) ?
C34 C35 . 1.516(13) ?
C34 H34 . 1.0000 ?
C35 H35A . 0.9800 ?
C35 H35B . 0.9800 ?
C35 H35C . 0.9800 ?
C36 H36A . 0.9800 ?
C36 H36B . 0.9800 ?
C36 H36C . 0.9800 ?
C37 H37A . 0.9800 ?
C37 H37B . 0.9800 ?
C37 H37C . 0.9800 ?
C38 C45 . 1.383(10) ?
C38 C39 . 1.482(10) ?
C39 C40 . 1.397(10) ?
C39 C44 . 1.409(10) ?
C40 C41 . 1.379(11) ?
C40 H40 . 0.9500 ?
C41 C42 . 1.397(11) ?
C41 H41 . 0.9500 ?
C42 C43 . 1.373(12) ?
C42 H42 . 0.9500 ?
C43 C44 . 1.401(10) ?
C43 H43 . 0.9500 ?
C44 H44 . 0.9500 ?
C45 C46 . 1.409(11) ?
C45 C50 . 1.511(9) ?
C46 C47 . 1.536(8) ?
C47 C52 . 1.516(9) ?
C47 C51 . 1.553(7) ?
C47 C48 . 1.583(7) ?
C48 C49 . 1.543(7) ?
C48 H48A . 0.9900 ?
C48 H48B . 0.9900 ?
C49 C50 . 1.555(7) ?
C49 H49A . 0.9900 ?
C49 H49B . 0.9900 ?
C50 C51 . 1.553(6) ?
C50 H50 . 1.0000 ?
C51 C53 . 1.532(9) ?
C51 C54 . 1.536(7) ?
C52 H52A . 0.9800 ?
C52 H52B . 0.9800 ?
C52 H52C . 0.9800 ?
C53 H53A . 0.9800 ?
C53 H53B . 0.9800 ?
C53 H53C . 0.9800 ?
C54 H54A . 0.9800 ?
C54 H54B . 0.9800 ?
C54 H54C . 0.9800 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C43 H43 Cl1 . 0.95 2.69 3.605(7) 161.9
C14 H14 Cl2 . 0.95 2.78 3.731(7) 178.1
