#------------------------------------------------------------------------------
#$Date: 2016-03-23 03:41:20 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179257 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/77/4317700.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_4317700
loop_
_publ_author_name
'Pia I. Anderberg'
'Margaret M. Harding'
'Ian J. Luck'
'Peter Turner'
_publ_contact_author_address
;
  School of Chemistry, University of Sydney, N.S.W. 2006, Australia
;
_publ_contact_author_email       m.harding@chem.usyd.edu.au
_publ_contact_author_fax         61-2-9351-3329
_publ_contact_author_name        'Margaret M. Harding'
_publ_contact_author_phone       61-2-9351-2745
_publ_section_title
;
 Ruthenium Complexes of Analogues of the Antitumor Antibiotic
 Streptonigrin
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1365
_journal_page_last               1371
_journal_paper_doi               10.1021/ic010876m
_journal_volume                  41
_journal_year                    2002
_chemical_formula_sum            'C16 H12 Cl2 N2 O6 Ru'
_chemical_formula_weight         500.25
_chemical_name_systematic
;
  ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.780(4)
_cell_angle_beta                 100.158(4)
_cell_angle_gamma                100.539(4)
_cell_formula_units_Z            2
_cell_length_a                   8.917(2)
_cell_length_b                   13.569(3)
_cell_length_c                   7.827(2)
_cell_measurement_reflns_used    954
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.115
_cell_measurement_theta_min      2.658
_cell_volume                     911.7(4)
_computing_cell_refinement       'SAINT (Bruker,1995)'
_computing_data_collection       'SMART (Bruker,1995)'
_computing_data_reduction        'SAINT and XPREP (Bruker 1995)'
_computing_molecular_graphics    'teXsan for Windows (MSC, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.917
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9265
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.53
_diffrn_standards_decay_%        0.001
_diffrn_standards_number         155
_exptl_absorpt_coefficient_mu    1.189
_exptl_absorpt_correction_T_max  0.91428
_exptl_absorpt_correction_T_min  0.58659
_exptl_absorpt_correction_type   'numerical and empirical'
_exptl_absorpt_process_details
;
   Gaussian (XPREP, Bruker 1995) and SADABS (Sheldrick, 1996)
;
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.079
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4153
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0203
_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)+(0.0303P)²+0.2564P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0544
_reflns_number_gt                3890
_reflns_number_total             4153
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic010876m.cif
_cod_data_source_block           mmh23
_cod_original_cell_volume        911.6(4)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4317700
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
Ru1 Ru 0.736852(15) 0.210302(9) 0.275966(16) 0.03323(5) Uani 1 1 d . . .
Cl1 Cl 0.71559(6) 0.31114(4) 0.03727(6) 0.04801(11) Uani 1 1 d . . .
Cl2 Cl 1.01539(5) 0.23757(3) 0.27701(6) 0.04247(10) Uani 1 1 d . . .
O1 O 0.7068(2) 0.03316(13) 0.0151(2) 0.0681(4) Uani 1 1 d . . .
O2 O 0.39018(18) 0.16516(13) 0.2468(2) 0.0665(4) Uani 1 1 d . . .
O3 O 0.50685(16) 0.38948(11) 0.28792(18) 0.0496(3) Uani 1 1 d . . .
O4 O 0.6639(2) 0.53222(12) 0.2449(2) 0.0667(4) Uani 1 1 d . . .
O5 O 0.7245(2) -0.11971(11) 0.3924(2) 0.0657(4) Uani 1 1 d . . .
O6 O 0.55076(19) -0.02094(12) 0.3280(2) 0.0636(4) Uani 1 1 d . . .
N1 N 0.78183(17) 0.33640(11) 0.47311(18) 0.0361(3) Uani 1 1 d . . .
N2 N 0.79593(17) 0.14253(11) 0.50797(18) 0.0361(3) Uani 1 1 d . . .
C1 C 0.7159(2) 0.09620(16) 0.1099(2) 0.0441(4) Uani 1 1 d . . .
C2 C 0.5206(2) 0.18334(14) 0.2637(2) 0.0431(4) Uani 1 1 d . . .
C3 C 0.7576(2) 0.43142(13) 0.4603(2) 0.0403(4) Uani 1 1 d . . .
C4 C 0.8342(2) 0.51107(14) 0.5827(3) 0.0479(4) Uani 1 1 d . . .
H4 H 0.8168 0.5758 0.5683 0.057 Uiso 1 1 calc R . .
C5 C 0.9361(3) 0.49380(15) 0.7254(3) 0.0498(5) Uani 1 1 d . . .
H5 H 0.9915 0.5468 0.8067 0.060 Uiso 1 1 calc R . .
C6 C 0.9546(2) 0.39612(15) 0.7459(2) 0.0463(4) Uani 1 1 d . . .
H6 H 1.0197 0.3823 0.8442 0.056 Uiso 1 1 calc R . .
C7 C 0.8756(2) 0.31856(13) 0.6191(2) 0.0378(3) Uani 1 1 d . . .
C8 C 0.8834(2) 0.21190(13) 0.6383(2) 0.0387(4) Uani 1 1 d . . .
C9 C 0.9693(2) 0.18321(16) 0.7860(2) 0.0487(4) Uani 1 1 d . . .
H9 H 1.0243 0.2314 0.8760 0.058 Uiso 1 1 calc R . .
C10 C 0.9722(3) 0.08288(17) 0.7979(3) 0.0525(5) Uani 1 1 d . . .
H10 H 1.0351 0.0631 0.8920 0.063 Uiso 1 1 calc R . .
C11 C 0.8811(2) 0.01201(15) 0.6691(3) 0.0477(4) Uani 1 1 d . . .
H11 H 0.8799 -0.0562 0.6765 0.057 Uiso 1 1 calc R . .
C12 C 0.7912(2) 0.04396(13) 0.5282(2) 0.0402(4) Uani 1 1 d . . .
C13 C 0.6407(2) 0.45612(15) 0.3138(3) 0.0472(4) Uani 1 1 d . . .
C14 C 0.3901(3) 0.4038(2) 0.1407(3) 0.0638(6) Uani 1 1 d . . .
H14A H 0.3705 0.4708 0.1543 0.096 Uiso 1 1 calc R . .
H14B H 0.2956 0.3559 0.1367 0.096 Uiso 1 1 calc R . .
H14C H 0.4274 0.3941 0.0342 0.096 Uiso 1 1 calc R . .
C15 C 0.6730(2) -0.03362(14) 0.4022(3) 0.0465(4) Uani 1 1 d . . .
C16 C 0.6147(4) -0.20441(19) 0.2894(4) 0.0943(10) Uani 1 1 d . . .
H16A H 0.5190 -0.2138 0.3321 0.141 Uiso 1 1 calc R . .
H16B H 0.6574 -0.2643 0.2989 0.141 Uiso 1 1 calc R . .
H16C H 0.5953 -0.1910 0.1695 0.141 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'
Cl Cl 0.1484 0.1585 '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
C2 Ru1 C1 89.89(8) . . ?
C2 Ru1 N2 96.91(7) . . ?
C1 Ru1 N2 98.95(7) . . ?
C2 Ru1 N1 94.78(7) . . ?
C1 Ru1 N1 174.62(7) . . ?
N2 Ru1 N1 77.87(6) . . ?
C2 Ru1 Cl1 92.05(6) . . ?
C1 Ru1 Cl1 87.99(6) . . ?
N2 Ru1 Cl1 168.65(4) . . ?
N1 Ru1 Cl1 94.49(4) . . ?
C2 Ru1 Cl2 176.53(6) . . ?
C1 Ru1 Cl2 86.68(6) . . ?
N2 Ru1 Cl2 84.17(4) . . ?
N1 Ru1 Cl2 88.67(4) . . ?
Cl1 Ru1 Cl2 87.299(17) . . ?
C13 O3 C14 115.07(17) . . ?
C15 O5 C16 115.2(2) . . ?
C3 N1 C7 117.77(15) . . ?
C3 N1 Ru1 130.22(12) . . ?
C7 N1 Ru1 110.58(11) . . ?
C12 N2 C8 118.06(15) . . ?
C12 N2 Ru1 128.63(12) . . ?
C8 N2 Ru1 111.17(11) . . ?
O1 C1 Ru1 178.41(19) . . ?
O2 C2 Ru1 176.12(18) . . ?
N1 C3 C4 122.51(18) . . ?
N1 C3 C13 121.61(16) . . ?
C4 C3 C13 115.86(17) . . ?
C5 C4 C3 119.47(18) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 118.68(17) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C7 119.73(18) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
N1 C7 C6 121.59(17) . . ?
N1 C7 C8 116.05(15) . . ?
C6 C7 C8 122.31(17) . . ?
N2 C8 C9 121.55(17) . . ?
N2 C8 C7 116.72(15) . . ?
C9 C8 C7 121.65(16) . . ?
C10 C9 C8 119.41(19) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C11 119.39(19) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 119.03(18) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 H11 120.5 . . ?
N2 C12 C11 122.28(17) . . ?
N2 C12 C15 118.58(16) . . ?
C11 C12 C15 118.89(17) . . ?
O4 C13 O3 125.9(2) . . ?
O4 C13 C3 122.37(19) . . ?
O3 C13 C3 111.35(16) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O6 C15 O5 125.29(19) . . ?
O6 C15 C12 125.25(19) . . ?
O5 C15 C12 109.40(18) . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
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 C2 1.880(2) . ?
Ru1 C1 1.914(2) . ?
Ru1 N2 2.1167(14) . ?
Ru1 N1 2.1567(14) . ?
Ru1 Cl1 2.3886(7) . ?
Ru1 Cl2 2.4417(8) . ?
O1 C1 1.076(2) . ?
O2 C2 1.126(2) . ?
O3 C13 1.334(2) . ?
O3 C14 1.459(2) . ?
O4 C13 1.198(2) . ?
O5 C15 1.333(3) . ?
O5 C16 1.455(3) . ?
O6 C15 1.189(3) . ?
N1 C3 1.353(2) . ?
N1 C7 1.355(2) . ?
N2 C12 1.351(2) . ?
N2 C8 1.363(2) . ?
C3 C4 1.384(3) . ?
C3 C13 1.507(3) . ?
C4 C5 1.372(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.391(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.478(2) . ?
C8 C9 1.389(3) . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 C15 1.511(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
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
C2 Ru1 N1 C3 -75.03(16) . . . . ?
C1 Ru1 N1 C3 134.7(7) . . . . ?
N2 Ru1 N1 C3 -171.09(16) . . . . ?
Cl1 Ru1 N1 C3 17.41(15) . . . . ?
Cl2 Ru1 N1 C3 104.59(15) . . . . ?
C2 Ru1 N1 C7 119.23(13) . . . . ?
C1 Ru1 N1 C7 -31.0(7) . . . . ?
N2 Ru1 N1 C7 23.17(11) . . . . ?
Cl1 Ru1 N1 C7 -148.34(11) . . . . ?
Cl2 Ru1 N1 C7 -61.15(11) . . . . ?
C2 Ru1 N2 C12 80.66(16) . . . . ?
C1 Ru1 N2 C12 -10.33(16) . . . . ?
N1 Ru1 N2 C12 174.08(16) . . . . ?
Cl1 Ru1 N2 C12 -137.48(17) . . . . ?
Cl2 Ru1 N2 C12 -96.03(15) . . . . ?
C2 Ru1 N2 C8 -116.55(13) . . . . ?
C1 Ru1 N2 C8 152.47(12) . . . . ?
N1 Ru1 N2 C8 -23.12(12) . . . . ?
Cl1 Ru1 N2 C8 25.3(3) . . . . ?
Cl2 Ru1 N2 C8 66.77(11) . . . . ?
C2 Ru1 C1 O1 147(7) . . . . ?
N2 Ru1 C1 O1 -116(7) . . . . ?
N1 Ru1 C1 O1 -62(8) . . . . ?
Cl1 Ru1 C1 O1 55(7) . . . . ?
Cl2 Ru1 C1 O1 -32(7) . . . . ?
C1 Ru1 C2 O2 -32(3) . . . . ?
N2 Ru1 C2 O2 -131(3) . . . . ?
N1 Ru1 C2 O2 151(3) . . . . ?
Cl1 Ru1 C2 O2 56(3) . . . . ?
Cl2 Ru1 C2 O2 -23(3) . . . . ?
C7 N1 C3 C4 5.4(3) . . . . ?
Ru1 N1 C3 C4 -159.53(14) . . . . ?
C7 N1 C3 C13 -172.62(16) . . . . ?
Ru1 N1 C3 C13 22.5(3) . . . . ?
N1 C3 C4 C5 -1.7(3) . . . . ?
C13 C3 C4 C5 176.39(18) . . . . ?
C3 C4 C5 C6 -2.4(3) . . . . ?
C4 C5 C6 C7 2.7(3) . . . . ?
C3 N1 C7 C6 -5.0(3) . . . . ?
Ru1 N1 C7 C6 162.75(14) . . . . ?
C3 N1 C7 C8 172.55(15) . . . . ?
Ru1 N1 C7 C8 -19.72(18) . . . . ?
C5 C6 C7 N1 1.0(3) . . . . ?
C5 C6 C7 C8 -176.35(18) . . . . ?
C12 N2 C8 C9 1.8(3) . . . . ?
Ru1 N2 C8 C9 -163.01(15) . . . . ?
C12 N2 C8 C7 -174.99(15) . . . . ?
Ru1 N2 C8 C7 20.18(19) . . . . ?
N1 C7 C8 N2 0.0(2) . . . . ?
C6 C7 C8 N2 177.52(17) . . . . ?
N1 C7 C8 C9 -176.79(17) . . . . ?
C6 C7 C8 C9 0.7(3) . . . . ?
N2 C8 C9 C10 3.1(3) . . . . ?
C7 C8 C9 C10 179.71(18) . . . . ?
C8 C9 C10 C11 -4.7(3) . . . . ?
C9 C10 C11 C12 1.5(3) . . . . ?
C8 N2 C12 C11 -5.2(3) . . . . ?
Ru1 N2 C12 C11 156.64(14) . . . . ?
C8 N2 C12 C15 168.94(16) . . . . ?
Ru1 N2 C12 C15 -29.3(2) . . . . ?
C10 C11 C12 N2 3.6(3) . . . . ?
C10 C11 C12 C15 -170.52(18) . . . . ?
C14 O3 C13 O4 11.3(3) . . . . ?
C14 O3 C13 C3 -176.17(16) . . . . ?
N1 C3 C13 O4 -141.6(2) . . . . ?
C4 C3 C13 O4 40.3(3) . . . . ?
N1 C3 C13 O3 45.5(2) . . . . ?
C4 C3 C13 O3 -132.62(18) . . . . ?
C16 O5 C15 O6 -3.7(3) . . . . ?
C16 O5 C15 C12 173.8(2) . . . . ?
N2 C12 C15 O6 -28.5(3) . . . . ?
C11 C12 C15 O6 145.8(2) . . . . ?
N2 C12 C15 O5 153.94(17) . . . . ?
C11 C12 C15 O5 -31.8(2) . . . . ?
