#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:11:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179316 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/13/4321391.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_4321391
loop_
_publ_author_name
'Scott B. Marr'
'Richard O. Carvel'
'David T. Richens'
'Hyun-Jin Lee'
'Michael Lane'
'Pericles Stavropoulos'
_publ_section_title
;
 Comparison between Iron and Ruthenium Reagents Mediating GifIV-Type
 Oxygenation of Cyclohexane
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4630
_journal_page_last               4638
_journal_paper_doi               10.1021/ic0001560
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C27 H33 N3 O13 Ru3'
_chemical_formula_weight         910.77
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           146
_symmetry_cell_setting           rhombohedral
_symmetry_space_group_name_Hall  'R 3'
_symmetry_space_group_name_H-M   'R 3 :H'
_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                120.00
_cell_formula_units_Z            3
_cell_length_a                   17.436(4)
_cell_length_b                   17.436(4)
_cell_length_c                   10.907(3)
_cell_measurement_reflns_used    117
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      20.65
_cell_measurement_theta_min      2.31
_cell_volume                     2871.6(12)
_computing_cell_refinement       'SMART (Bruker, V4.050, 1995)'
_computing_data_collection       'ASTRO (Bruker, V4.050, 1995)'
_computing_data_reduction        'SAINT (Bruker, V5.A06, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1998, ver 5.10)'
_computing_publication_material  'CIFTAB (Sheldrick, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.287
_diffrn_measured_fraction_theta_max 0.287
_diffrn_measurement_method       'ω, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            402
_diffrn_reflns_theta_full        26.98
_diffrn_reflns_theta_max         26.98
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.226
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            dark-red
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       hexagonal-plate
_exptl_crystal_F_000             1356
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.337
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         402
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.212
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0930P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1354
_reflns_number_gt                367
_reflns_number_total             402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0001560.cif
_cod_data_source_block           ps59_COMPOUND_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Rhombohedral' changed to
'rhombohedral' 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 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        2872(1)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               4321391
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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 -0.00004(10) 0.88966(10) 0.8418(4) 0.0246(7) Uani 1 1 d . . .
O1 O 0.0986(13) 0.9287(13) 0.708(2) 0.040(4) Uani 1 1 d U . .
O2 O 0.1665(12) 1.0771(13) 0.706(2) 0.044(4) Uani 1 1 d U . .
O3 O -0.0975(13) 0.8292(13) 0.973(3) 0.043(4) Uani 1 1 d U . .
O4 O -0.1678(12) 0.9084(13) 0.971(3) 0.042(4) Uani 1 1 d U . .
O5 O 0.0000 1.0000 0.842(3) 0.020(8) Uani 1 3 d S . .
C1 C 0.1538(19) 1.0024(19) 0.672(4) 0.041(4) Uani 1 1 d U . .
C2 C 0.2162(19) 1.000(2) 0.575(5) 0.048(6) Uani 1 1 d U . .
H2A H 0.2049 0.9399 0.5667 0.072 Uiso 1 1 calc R . .
H2B H 0.2771 1.0384 0.6008 0.072 Uiso 1 1 calc R . .
H2C H 0.2061 1.0204 0.4975 0.072 Uiso 1 1 calc R . .
C3 C -0.1537(19) 0.846(2) 1.013(4) 0.044(4) Uani 1 1 d U . .
C4 C -0.215(2) 0.787(2) 1.103(5) 0.052(5) Uani 1 1 d U . .
H4B H -0.2106 0.7342 1.1082 0.077 Uiso 1 1 calc R . .
H4C H -0.2748 0.7717 1.0799 0.077 Uiso 1 1 calc R . .
H4D H -0.2012 0.8165 1.1826 0.077 Uiso 1 1 calc R . .
N1 N -0.0013(10) 0.7699(8) 0.843(2) 0.041(4) Uani 1 1 d GU . .
C5 C 0.0781(9) 0.7709(9) 0.825(2) 0.041(4) Uani 1 1 d GU . .
H5A H 0.1308 0.8250 0.8137 0.050 Uiso 1 1 calc R . .
C6 C 0.0796(10) 0.6919(11) 0.825(3) 0.044(4) Uani 1 1 d GU . .
H6A H 0.1333 0.6926 0.8129 0.053 Uiso 1 1 calc R . .
C7 C 0.0017(12) 0.6120(9) 0.842(3) 0.046(4) Uani 1 1 d GU . .
H7A H 0.0027 0.5586 0.8421 0.056 Uiso 1 1 calc R . .
C8 C -0.0778(10) 0.6110(8) 0.860(3) 0.047(4) Uani 1 1 d GU . .
H8A H -0.1305 0.5569 0.8720 0.057 Uiso 1 1 calc R . .
C9 C -0.0792(9) 0.6899(10) 0.861(3) 0.044(4) Uani 1 1 d GU . .
H9A H -0.1330 0.6892 0.8728 0.053 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'
N N 0.0061 0.0033 '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'
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
O5 Ru1 O4 95.7(8) . 2_675 ?
O5 Ru1 O2 95.8(9) . 3_465 ?
O4 Ru1 O2 168.2(8) 2_675 3_465 ?
O5 Ru1 O3 95.6(9) . . ?
O4 Ru1 O3 89.9(11) 2_675 . ?
O2 Ru1 O3 91.2(11) 3_465 . ?
O5 Ru1 N1 179.2(11) . . ?
O4 Ru1 N1 84.2(8) 2_675 . ?
O2 Ru1 N1 84.3(8) 3_465 . ?
O3 Ru1 N1 83.6(8) . . ?
O5 Ru1 O1 95.0(9) . . ?
O4 Ru1 O1 89.4(10) 2_675 . ?
O2 Ru1 O1 87.5(10) 3_465 . ?
O3 Ru1 O1 169.4(8) . . ?
N1 Ru1 O1 85.8(8) . . ?
C1 O1 Ru1 130.6(18) . . ?
C1 O2 Ru1 131(2) . 2_675 ?
C3 O3 Ru1 132.5(17) . . ?
C3 O4 Ru1 133.7(19) . 3_465 ?
Ru1 O5 Ru1 119.999(14) 2_675 . ?
Ru1 O5 Ru1 119.999(14) 2_675 3_465 ?
Ru1 O5 Ru1 119.999(15) . 3_465 ?
O1 C1 O2 129(3) . . ?
O1 C1 C2 113(2) . . ?
O2 C1 C2 118(2) . . ?
O3 C3 O4 124(3) . . ?
O3 C3 C4 118(2) . . ?
O4 C3 C4 117(3) . . ?
C5 N1 C9 120.0 . . ?
C5 N1 Ru1 118.5(7) . . ?
C9 N1 Ru1 121.5(7) . . ?
C6 C5 N1 120.0 . . ?
C5 C6 C7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C7 C8 C9 120.0 . . ?
C8 C9 N1 120.0 . . ?
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 O5 1.9236(15) . ?
Ru1 O4 1.98(2) 2_675 ?
Ru1 O2 2.01(2) 3_465 ?
Ru1 O3 2.06(2) . ?
Ru1 N1 2.078(11) . ?
Ru1 O1 2.09(2) . ?
O1 C1 1.22(3) . ?
O2 C1 1.26(3) . ?
O2 Ru1 2.01(2) 2_675 ?
O3 C3 1.24(3) . ?
O4 C3 1.31(4) . ?
O4 Ru1 1.98(2) 3_465 ?
O5 Ru1 1.9236(15) 2_675 ?
O5 Ru1 1.9236(15) 3_465 ?
C1 C2 1.53(5) . ?
C3 C4 1.44(5) . ?
N1 C5 1.3900 . ?
N1 C9 1.3900 . ?
C5 C6 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
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
O5 Ru1 O1 C1 19(3) . . . . ?
O4 Ru1 O1 C1 -77(3) 2_675 . . . ?
O2 Ru1 O1 C1 115(3) 3_465 . . . ?
O3 Ru1 O1 C1 -163(6) . . . . ?
N1 Ru1 O1 C1 -161(3) . . . . ?
O5 Ru1 O3 C3 17(4) . . . . ?
O4 Ru1 O3 C3 113(4) 2_675 . . . ?
O2 Ru1 O3 C3 -79(4) 3_465 . . . ?
N1 Ru1 O3 C3 -163(4) . . . . ?
O1 Ru1 O3 C3 -161(5) . . . . ?
O4 Ru1 O5 Ru1 45.7(19) 2_675 . . 2_675 ?
O2 Ru1 O5 Ru1 -132.1(19) 3_465 . . 2_675 ?
O3 Ru1 O5 Ru1 136.2(19) . . . 2_675 ?
N1 Ru1 O5 Ru1 130(70) . . . 2_675 ?
O1 Ru1 O5 Ru1 -44.1(18) . . . 2_675 ?
O4 Ru1 O5 Ru1 -134.9(19) 2_675 . . 3_465 ?
O2 Ru1 O5 Ru1 47.3(19) 3_465 . . 3_465 ?
O3 Ru1 O5 Ru1 -44.4(19) . . . 3_465 ?
N1 Ru1 O5 Ru1 -51(73) . . . 3_465 ?
O1 Ru1 O5 Ru1 135.3(19) . . . 3_465 ?
Ru1 O1 C1 O2 0(6) . . . . ?
Ru1 O1 C1 C2 177(3) . . . . ?
Ru1 O2 C1 O1 6(6) 2_675 . . . ?
Ru1 O2 C1 C2 -172(3) 2_675 . . . ?
Ru1 O3 C3 O4 6(6) . . . . ?
Ru1 O3 C3 C4 178(3) . . . . ?
Ru1 O4 C3 O3 -3(6) 3_465 . . . ?
Ru1 O4 C3 C4 -176(3) 3_465 . . . ?
O5 Ru1 N1 C5 -139(71) . . . . ?
O4 Ru1 N1 C5 -54.8(13) 2_675 . . . ?
O2 Ru1 N1 C5 122.9(15) 3_465 . . . ?
O3 Ru1 N1 C5 -145.3(15) . . . . ?
O1 Ru1 N1 C5 35.0(14) . . . . ?
O5 Ru1 N1 C9 42(73) . . . . ?
O4 Ru1 N1 C9 125.7(15) 2_675 . . . ?
O2 Ru1 N1 C9 -56.7(15) 3_465 . . . ?
O3 Ru1 N1 C9 35.2(15) . . . . ?
O1 Ru1 N1 C9 -144.5(14) . . . . ?
C9 N1 C5 C6 0.0 . . . . ?
Ru1 N1 C5 C6 -179.5(17) . . . . ?
N1 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C8 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 N1 0.0 . . . . ?
C5 N1 C9 C8 0.0 . . . . ?
Ru1 N1 C9 C8 179.5(17) . . . . ?
