#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:43:39 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179860 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/56/7015655.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_7015655
loop_
_publ_author_name
'Bratsos, Ioannis'
'Urankar, Damijana'
'Zangrando, Ennio'
'Genova-Kalou, Petia'
'Košmrlj, Janez'
'Alessio, Enzo'
'Turel, Iztok'
_publ_section_title
;
 1-(2-Picolyl)-substituted 1,2,3-triazole as novel chelating ligand for
 the preparation of ruthenium complexes with potential anticancer
 activity.
;
_journal_issue                   19
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5188
_journal_page_last               5199
_journal_paper_doi               10.1039/c0dt01807d
_journal_volume                  40
_journal_year                    2011
_chemical_formula_moiety         'C18 H24 Cl2 N4 O2 Ru S2'
_chemical_formula_sum            'C18 H24 Cl2 N4 O2 Ru S2'
_chemical_formula_weight         564.50
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_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                104.37(3)
_cell_angle_beta                 96.23(2)
_cell_angle_gamma                94.18(2)
_cell_formula_units_Z            2
_cell_length_a                   8.411(3)
_cell_length_b                   10.009(4)
_cell_length_c                   13.997(4)
_cell_measurement_temperature    293(2)
_cell_volume                     1128.6(7)
_computing_cell_refinement       'Denzo (Otwinowski & Minor 1997)'
_computing_data_collection       'Nonius Xpress'
_computing_data_reduction
'Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep3/windows (Farrugia,1997)'
_computing_publication_material  'Wingx 1.70.00 (Farrugia, 1999)'
_computing_structure_refinement  'SHELX97 (Sheldrick, 1998)'
_computing_structure_solution    'SHELX97 (Sheldrick, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'image plate dip1030'
_diffrn_measurement_method       'laser scanner'
_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  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0872
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13115
_diffrn_reflns_theta_full        27.08
_diffrn_reflns_theta_max         27.08
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    1.139
_exptl_absorpt_correction_T_max  0.8255
_exptl_absorpt_correction_T_min  0.7565
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
Parkin S,Moezzi B & Hope H, (1995) J. Appl. Cryst. 28, 53-56
Quadratic fit to sin(theta)/lambda - 18 parameters
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.661
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.653
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.839
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.839
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0421
_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)+(0.0449P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.1070
_reflns_number_gt                2373
_reflns_number_total             4678
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0dt01807d.txt
_cod_data_source_block           1
_cod_database_code               7015655
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
Ru Ru 0.34273(5) 0.31858(4) 0.20544(3) 0.05167(15) Uani 1 1 d . . .
Cl2 Cl 0.21352(17) 0.39224(15) 0.35130(11) 0.0670(4) Uani 1 1 d . . .
Cl1 Cl 0.47402(16) 0.24177(14) 0.05802(11) 0.0629(4) Uani 1 1 d . . .
S1 S 0.54170(16) 0.49599(14) 0.26383(11) 0.0606(4) Uani 1 1 d . . .
S2 S 0.19410(16) 0.44525(14) 0.12158(12) 0.0599(4) Uani 1 1 d . . .
O1 O 0.5358(5) 0.6223(4) 0.2270(3) 0.0795(12) Uani 1 1 d . . .
O2 O 0.0387(4) 0.3729(4) 0.0660(3) 0.0799(12) Uani 1 1 d . . .
N1 N 0.1560(5) 0.1453(4) 0.1631(3) 0.0536(11) Uani 1 1 d . . .
N2 N 0.4672(5) 0.1827(4) 0.2721(3) 0.0524(11) Uani 1 1 d . . .
N3 N 0.4497(5) 0.0435(4) 0.2309(3) 0.0565(11) Uani 1 1 d . . .
N4 N 0.5610(5) 0.2091(4) 0.3564(3) 0.0585(11) Uani 1 1 d . . .
C1 C 0.0014(6) 0.1706(6) 0.1696(4) 0.0642(15) Uani 1 1 d . . .
H1 H -0.0202 0.2614 0.1956 0.077 Uiso 1 1 calc R . .
C2 C -0.1266(7) 0.0676(7) 0.1393(5) 0.0735(17) Uani 1 1 d . . .
H2 H -0.2317 0.0887 0.1444 0.088 Uiso 1 1 calc R . .
C3 C -0.0942(8) -0.0658(7) 0.1018(5) 0.0786(19) Uani 1 1 d . . .
H3 H -0.1777 -0.1366 0.0784 0.094 Uiso 1 1 calc R . .
C4 C 0.0633(7) -0.0945(6) 0.0991(4) 0.0692(16) Uani 1 1 d . . .
H4 H 0.0870 -0.1850 0.0750 0.083 Uiso 1 1 calc R . .
C5 C 0.1845(6) 0.0115(5) 0.1320(4) 0.0561(13) Uani 1 1 d . . .
C6 C 0.3575(6) -0.0202(5) 0.1344(4) 0.0606(14) Uani 1 1 d . . .
H6A H 0.3611 -0.1198 0.1190 0.073 Uiso 1 1 calc R . .
H6B H 0.4056 0.0137 0.0838 0.073 Uiso 1 1 calc R . .
C7 C 0.5383(6) -0.0171(6) 0.2922(4) 0.0632(15) Uani 1 1 d . . .
H7 H 0.5496 -0.1111 0.2824 0.076 Uiso 1 1 calc R . .
C8 C 0.6063(6) 0.0867(6) 0.3700(4) 0.0595(14) Uani 1 1 d . . .
C9 C 0.7138(7) 0.0818(6) 0.4594(4) 0.0641(15) Uani 1 1 d . . .
C10 C 0.7059(7) -0.0352(7) 0.4944(5) 0.0797(19) Uani 1 1 d . . .
H10 H 0.6296 -0.1091 0.4621 0.096 Uiso 1 1 calc R . .
C11 C 0.8080(9) -0.0464(9) 0.5763(6) 0.100(2) Uani 1 1 d . . .
H11 H 0.7997 -0.1253 0.6000 0.120 Uiso 1 1 calc R . .
C12 C 0.9200(10) 0.0614(11) 0.6203(6) 0.102(3) Uani 1 1 d . . .
H12 H 0.9918 0.0541 0.6737 0.122 Uiso 1 1 calc R . .
C13 C 0.9320(8) 0.1798(9) 0.5898(5) 0.097(2) Uani 1 1 d . . .
H13 H 1.0091 0.2526 0.6230 0.117 Uiso 1 1 calc R . .
C14 C 0.8278(7) 0.1916(7) 0.5083(5) 0.0836(19) Uani 1 1 d . . .
H14 H 0.8348 0.2724 0.4869 0.100 Uiso 1 1 calc R . .
C15 C 0.7337(6) 0.4394(6) 0.2475(5) 0.0783(18) Uani 1 1 d . . .
H15A H 0.7419 0.4084 0.1778 0.117 Uiso 1 1 calc R . .
H15B H 0.7484 0.3643 0.2779 0.117 Uiso 1 1 calc R . .
H15C H 0.8152 0.5147 0.2780 0.117 Uiso 1 1 calc R . .
C16 C 0.5687(8) 0.5564(6) 0.3955(4) 0.0840(19) Uani 1 1 d . . .
H16A H 0.6659 0.6183 0.4169 0.126 Uiso 1 1 calc R . .
H16B H 0.5760 0.4791 0.4242 0.126 Uiso 1 1 calc R . .
H16C H 0.4789 0.6047 0.4165 0.126 Uiso 1 1 calc R . .
C17 C 0.1499(8) 0.6020(6) 0.2000(5) 0.0812(18) Uani 1 1 d . . .
H17A H 0.0727 0.6436 0.1639 0.122 Uiso 1 1 calc R . .
H17B H 0.2465 0.6644 0.2221 0.122 Uiso 1 1 calc R . .
H17C H 0.1064 0.5833 0.2565 0.122 Uiso 1 1 calc R . .
C18 C 0.2898(7) 0.5120(6) 0.0345(5) 0.0749(17) Uani 1 1 d . . .
H18A H 0.3186 0.4367 -0.0158 0.112 Uiso 1 1 calc R . .
H18B H 0.3851 0.5711 0.0678 0.112 Uiso 1 1 calc R . .
H18C H 0.2179 0.5643 0.0041 0.112 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'
S S 0.1246 0.1234 '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
N2 Ru N1 82.89(16) . . ?
N2 Ru S1 93.20(12) . . ?
N1 Ru S1 174.72(12) . . ?
N2 Ru S2 173.94(13) . . ?
N1 Ru S2 91.76(11) . . ?
S1 Ru S2 92.31(6) . . ?
N2 Ru Cl2 90.05(12) . . ?
N1 Ru Cl2 85.26(12) . . ?
S1 Ru Cl2 91.20(6) . . ?
S2 Ru Cl2 92.35(6) . . ?
N2 Ru Cl1 89.44(12) . . ?
N1 Ru Cl1 94.43(12) . . ?
S1 Ru Cl1 89.07(6) . . ?
S2 Ru Cl1 88.13(6) . . ?
Cl2 Ru Cl1 179.43(5) . . ?
O1 S1 C15 106.4(3) . . ?
O1 S1 C16 105.3(3) . . ?
C15 S1 C16 98.8(3) . . ?
O1 S1 Ru 119.57(17) . . ?
C15 S1 Ru 111.6(2) . . ?
C16 S1 Ru 112.9(2) . . ?
O2 S2 C18 105.0(3) . . ?
O2 S2 C17 106.6(3) . . ?
C18 S2 C17 99.5(3) . . ?
O2 S2 Ru 115.30(16) . . ?
C18 S2 Ru 116.1(2) . . ?
C17 S2 Ru 112.7(2) . . ?
C5 N1 C1 117.0(4) . . ?
C5 N1 Ru 124.0(3) . . ?
C1 N1 Ru 119.0(4) . . ?
N4 N2 N3 108.7(4) . . ?
N4 N2 Ru 129.5(3) . . ?
N3 N2 Ru 121.6(3) . . ?
C7 N3 N2 108.3(4) . . ?
C7 N3 C6 128.9(5) . . ?
N2 N3 C6 122.7(4) . . ?
N2 N4 C8 107.9(4) . . ?
N1 C1 C2 123.1(6) . . ?
C3 C2 C1 118.3(6) . . ?
C2 C3 C4 119.4(6) . . ?
C5 C4 C3 119.5(6) . . ?
N1 C5 C4 122.5(5) . . ?
N1 C5 C6 117.8(4) . . ?
C4 C5 C6 119.7(5) . . ?
N3 C6 C5 111.6(4) . . ?
C8 C7 N3 105.9(5) . . ?
C7 C8 N4 109.2(5) . . ?
C7 C8 C9 129.7(5) . . ?
N4 C8 C9 121.1(5) . . ?
C10 C9 C14 118.4(6) . . ?
C10 C9 C8 120.1(6) . . ?
C14 C9 C8 121.4(6) . . ?
C9 C10 C11 122.2(7) . . ?
C12 C11 C10 117.6(7) . . ?
C11 C12 C13 122.8(8) . . ?
C12 C13 C14 119.5(7) . . ?
C9 C14 C13 119.5(7) . . ?
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
Ru N2 2.107(4) . ?
Ru N1 2.172(4) . ?
Ru S1 2.2740(16) . ?
Ru S2 2.2802(15) . ?
Ru Cl2 2.3967(16) . ?
Ru Cl1 2.4289(16) . ?
S1 O1 1.481(4) . ?
S1 C15 1.770(6) . ?
S1 C16 1.774(6) . ?
S2 O2 1.483(4) . ?
S2 C18 1.766(5) . ?
S2 C17 1.768(6) . ?
N1 C5 1.349(6) . ?
N1 C1 1.351(6) . ?
N2 N4 1.303(5) . ?
N2 N3 1.360(5) . ?
N3 C7 1.359(6) . ?
N3 C6 1.451(6) . ?
N4 C8 1.360(6) . ?
C1 C2 1.387(7) . ?
C2 C3 1.367(8) . ?
C3 C4 1.378(8) . ?
C4 C5 1.369(7) . ?
C5 C6 1.510(7) . ?
C7 C8 1.345(7) . ?
C8 C9 1.476(7) . ?
C9 C10 1.376(8) . ?
C9 C14 1.388(8) . ?
C10 C11 1.389(9) . ?
C11 C12 1.352(10) . ?
C12 C13 1.356(10) . ?
C13 C14 1.396(9) . ?
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
N2 Ru S1 O1 170.2(2) . . . . ?
N1 Ru S1 O1 -147.6(13) . . . . ?
S2 Ru S1 O1 -7.3(2) . . . . ?
Cl2 Ru S1 O1 -99.7(2) . . . . ?
Cl1 Ru S1 O1 80.8(2) . . . . ?
N2 Ru S1 C15 45.0(3) . . . . ?
N1 Ru S1 C15 87.2(13) . . . . ?
S2 Ru S1 C15 -132.4(2) . . . . ?
Cl2 Ru S1 C15 135.2(2) . . . . ?
Cl1 Ru S1 C15 -44.3(2) . . . . ?
N2 Ru S1 C16 -65.3(3) . . . . ?
N1 Ru S1 C16 -23.0(13) . . . . ?
S2 Ru S1 C16 117.3(3) . . . . ?
Cl2 Ru S1 C16 24.9(3) . . . . ?
Cl1 Ru S1 C16 -154.6(3) . . . . ?
N2 Ru S2 O2 24.7(12) . . . . ?
N1 Ru S2 O2 -3.2(2) . . . . ?
S1 Ru S2 O2 -179.9(2) . . . . ?
Cl2 Ru S2 O2 -88.6(2) . . . . ?
Cl1 Ru S2 O2 91.1(2) . . . . ?
N2 Ru S2 C18 -98.7(11) . . . . ?
N1 Ru S2 C18 -126.6(3) . . . . ?
S1 Ru S2 C18 56.8(3) . . . . ?
Cl2 Ru S2 C18 148.1(3) . . . . ?
Cl1 Ru S2 C18 -32.2(3) . . . . ?
N2 Ru S2 C17 147.5(11) . . . . ?
N1 Ru S2 C17 119.5(3) . . . . ?
S1 Ru S2 C17 -57.1(2) . . . . ?
Cl2 Ru S2 C17 34.2(2) . . . . ?
Cl1 Ru S2 C17 -146.1(2) . . . . ?
N2 Ru N1 C5 -40.3(4) . . . . ?
S1 Ru N1 C5 -82.8(14) . . . . ?
S2 Ru N1 C5 136.9(4) . . . . ?
Cl2 Ru N1 C5 -130.9(4) . . . . ?
Cl1 Ru N1 C5 48.6(4) . . . . ?
N2 Ru N1 C1 138.3(4) . . . . ?
S1 Ru N1 C1 95.8(13) . . . . ?
S2 Ru N1 C1 -44.5(4) . . . . ?
Cl2 Ru N1 C1 47.7(4) . . . . ?
Cl1 Ru N1 C1 -132.8(4) . . . . ?
N1 Ru N2 N4 -141.3(4) . . . . ?
S1 Ru N2 N4 35.1(4) . . . . ?
S2 Ru N2 N4 -169.5(8) . . . . ?
Cl2 Ru N2 N4 -56.1(4) . . . . ?
Cl1 Ru N2 N4 124.1(4) . . . . ?
N1 Ru N2 N3 34.4(4) . . . . ?
S1 Ru N2 N3 -149.2(3) . . . . ?
S2 Ru N2 N3 6.2(14) . . . . ?
Cl2 Ru N2 N3 119.6(3) . . . . ?
Cl1 Ru N2 N3 -60.2(3) . . . . ?
N4 N2 N3 C7 -0.8(6) . . . . ?
Ru N2 N3 C7 -177.3(3) . . . . ?
N4 N2 N3 C6 -177.5(4) . . . . ?
Ru N2 N3 C6 6.0(6) . . . . ?
N3 N2 N4 C8 0.6(5) . . . . ?
Ru N2 N4 C8 176.7(3) . . . . ?
C5 N1 C1 C2 -4.8(8) . . . . ?
Ru N1 C1 C2 176.5(4) . . . . ?
N1 C1 C2 C3 0.5(9) . . . . ?
C1 C2 C3 C4 2.6(9) . . . . ?
C2 C3 C4 C5 -1.3(9) . . . . ?
C1 N1 C5 C4 6.2(7) . . . . ?
Ru N1 C5 C4 -175.2(4) . . . . ?
C1 N1 C5 C6 -173.8(5) . . . . ?
Ru N1 C5 C6 4.8(7) . . . . ?
C3 C4 C5 N1 -3.3(8) . . . . ?
C3 C4 C5 C6 176.7(5) . . . . ?
C7 N3 C6 C5 124.7(5) . . . . ?
N2 N3 C6 C5 -59.3(6) . . . . ?
N1 C5 C6 N3 51.3(6) . . . . ?
C4 C5 C6 N3 -128.7(5) . . . . ?
N2 N3 C7 C8 0.7(6) . . . . ?
C6 N3 C7 C8 177.1(5) . . . . ?
N3 C7 C8 N4 -0.3(6) . . . . ?
N3 C7 C8 C9 179.6(5) . . . . ?
N2 N4 C8 C7 -0.2(6) . . . . ?
N2 N4 C8 C9 180.0(5) . . . . ?
C7 C8 C9 C10 -27.5(10) . . . . ?
N4 C8 C9 C10 152.3(5) . . . . ?
C7 C8 C9 C14 150.4(6) . . . . ?
N4 C8 C9 C14 -29.7(8) . . . . ?
C14 C9 C10 C11 -0.1(9) . . . . ?
C8 C9 C10 C11 177.9(6) . . . . ?
C9 C10 C11 C12 -1.5(10) . . . . ?
C10 C11 C12 C13 2.3(12) . . . . ?
C11 C12 C13 C14 -1.5(12) . . . . ?
C10 C9 C14 C13 1.0(9) . . . . ?
C8 C9 C14 C13 -177.0(6) . . . . ?
C12 C13 C14 C9 -0.2(10) . . . . ?
