#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:16:14 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185491 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/95/7039595.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_7039595
loop_
_publ_author_name
'Kljun, Jakob'
'Anko, Maja'
'Traven, Katja'
'Sinreih, Maša'
'Pavlič, Renata'
'Peršič, Špela'
'Ude, Žiga'
'Codina, Elisa Esteve'
'Stojan, Jure'
'Lanišnik Rižner, Tea'
'Turel, Iztok'
_publ_section_title
;
 Pyrithione-based ruthenium complexes as inhibitors of aldo-keto reductase
 1C enzymes and anticancer agents.
;
_journal_issue                   29
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11791
_journal_page_last               11800
_journal_paper_doi               10.1039/c6dt00668j
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety         'C13 H22 N O2 Ru S5, F6 P'
_chemical_formula_sum            'C13 H22 F6 N O2 P Ru S5'
_chemical_formula_weight         630.65
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-27 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                99.963(4)
_cell_angle_beta                 101.149(4)
_cell_angle_gamma                107.554(4)
_cell_formula_units_Z            2
_cell_length_a                   7.8145(3)
_cell_length_b                   12.1293(5)
_cell_length_c                   12.2989(5)
_cell_measurement_reflns_used    2532
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.5220
_cell_measurement_theta_min      3.7970
_cell_volume                     1056.61(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Dual, Mo at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10394
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.785
_exptl_absorpt_coefficient_mu    1.375
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.982
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4832
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0280
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0175P)²+0.0621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4018
_reflns_number_total             4832
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt00668j2.cif
_cod_data_source_block           moa226
_cod_depositor_comments
'Adding full bibliography for 7039593--7039596.cif.'
_cod_database_code               7039595
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.770
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Ru1 Ru 0.16629(2) 0.24910(2) 0.41510(2) 0.01203(6) Uani 1 1 d . .
S14 S -0.05170(8) 0.08543(5) 0.27633(5) 0.01652(14) Uani 1 1 d . .
S2 S 0.35024(8) 0.41841(5) 0.56670(5) 0.01666(14) Uani 1 1 d . .
S11 S -0.02749(8) 0.35848(6) 0.36970(5) 0.01857(14) Uani 1 1 d . .
S17 S 0.30397(8) 0.30032(6) 0.27331(5) 0.01774(14) Uani 1 1 d . .
S20 S 0.35652(8) 0.14594(5) 0.45989(5) 0.01447(13) Uani 1 1 d . .
P31 P 0.56739(9) 0.23381(6) -0.07765(6) 0.02202(16) Uani 1 1 d . .
F36 F 0.78073(19) 0.29489(15) -0.00250(13) 0.0359(4) Uani 1 1 d . .
F35 F 0.5356(2) 0.13592(16) -0.00515(15) 0.0479(5) Uani 1 1 d . .
F37 F 0.5089(2) 0.31639(15) 0.01367(14) 0.0417(5) Uani 1 1 d . .
F34 F 0.6272(2) 0.15109(16) -0.16675(15) 0.0458(5) Uani 1 1 d . .
F32 F 0.3564(2) 0.17429(15) -0.15040(14) 0.0405(5) Uani 1 1 d . .
O21 O 0.3597(2) 0.05338(16) 0.36503(14) 0.0232(4) Uani 1 1 d . .
F33 F 0.6029(2) 0.33301(16) -0.14780(15) 0.0468(5) Uani 1 1 d . .
O1 O 0.0259(2) 0.19911(14) 0.53660(13) 0.0163(4) Uani 1 1 d . .
N1 N 0.0903(2) 0.27381(17) 0.64374(16) 0.0148(4) Uani 1 1 d . .
C3 C 0.2897(3) 0.4479(2) 0.7820(2) 0.0189(6) Uani 1 1 d . .
H3 H 0.3903 0.5217 0.8030 0.023 Uiso 1 1 calc R U
C2 C 0.2363(3) 0.3778(2) 0.6694(2) 0.0156(5) Uani 1 1 d . .
C5 C 0.0536(3) 0.3049(2) 0.8310(2) 0.0235(6) Uani 1 1 d . .
H5 H -0.0100 0.2791 0.8856 0.028 Uiso 1 1 calc R U
C22 C 0.3104(3) 0.0755(2) 0.5710(2) 0.0233(6) Uani 1 1 d . .
H22A H 0.1900 0.0104 0.5431 0.035 Uiso 1 1 calc R U
H22B H 0.3074 0.1338 0.6359 0.035 Uiso 1 1 calc R U
H22C H 0.4084 0.0434 0.5954 0.035 Uiso 1 1 calc R U
C6 C 0.0009(3) 0.2364(2) 0.7221(2) 0.0185(6) Uani 1 1 d . .
H6 H -0.0987 0.1621 0.7008 0.022 Uiso 1 1 calc R U
C4 C 0.2011(3) 0.4131(2) 0.8622(2) 0.0235(6) Uani 1 1 d . .
H4 H 0.2394 0.4618 0.9380 0.028 Uiso 1 1 calc R U
C16 C 0.2125(3) 0.1639(2) 0.1582(2) 0.0253(6) Uani 1 1 d . .
H16A H 0.2326 0.1846 0.0862 0.030 Uiso 1 1 calc R U
H16B H 0.2828 0.1108 0.1758 0.030 Uiso 1 1 calc R U
C23 C 0.5931(3) 0.2384(2) 0.5257(2) 0.0254(6) Uani 1 1 d . .
H23A H 0.6709 0.1884 0.5307 0.038 Uiso 1 1 calc R U
H23B H 0.6037 0.2828 0.6026 0.038 Uiso 1 1 calc R U
H23C H 0.6347 0.2946 0.4797 0.038 Uiso 1 1 calc R U
C13 C -0.2590(3) 0.1271(2) 0.2551(2) 0.0198(6) Uani 1 1 d . .
H13A H -0.3488 0.0748 0.1828 0.024 Uiso 1 1 calc R U
H13B H -0.3178 0.1126 0.3182 0.024 Uiso 1 1 calc R U
C18 C 0.1845(3) 0.3936(2) 0.2112(2) 0.0253(6) Uani 1 1 d . .
H18A H 0.2726 0.4535 0.1844 0.030 Uiso 1 1 calc R U
H18B H 0.0807 0.3428 0.1443 0.030 Uiso 1 1 calc R U
C12 C -0.2219(3) 0.2560(2) 0.2504(2) 0.0224(6) Uani 1 1 d . .
H12A H -0.3351 0.2758 0.2532 0.027 Uiso 1 1 calc R U
H12B H -0.1929 0.2664 0.1772 0.027 Uiso 1 1 calc R U
C15 C 0.0067(3) 0.0968(3) 0.1405(2) 0.0257(6) Uani 1 1 d . .
H15A H -0.0274 0.0157 0.0913 0.031 Uiso 1 1 calc R U
H15B H -0.0668 0.1386 0.1006 0.031 Uiso 1 1 calc R U
C19 C 0.1094(3) 0.4567(2) 0.2973(2) 0.0270(7) Uani 1 1 d . .
H19A H 0.0310 0.4959 0.2577 0.032 Uiso 1 1 calc R U
H19B H 0.2150 0.5199 0.3554 0.032 Uiso 1 1 calc R U
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'
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
O1 Ru1 S20 91.49(5)
O1 Ru1 S17 176.57(4)
S20 Ru1 S17 90.68(2)
O1 Ru1 S14 89.79(4)
S20 Ru1 S14 92.72(2)
S17 Ru1 S14 87.44(2)
O1 Ru1 S11 88.81(5)
S20 Ru1 S11 179.22(2)
S17 Ru1 S11 89.07(2)
S14 Ru1 S11 88.01(2)
O1 Ru1 S2 83.60(4)
S20 Ru1 S2 92.83(2)
S17 Ru1 S2 98.96(2)
S14 Ru1 S2 171.47(2)
S11 Ru1 S2 86.49(2)
C13 S14 C15 100.05(12)
C13 S14 Ru1 102.66(8)
C15 S14 Ru1 106.51(8)
C2 S2 Ru1 97.11(8)
C19 S11 C12 102.09(12)
C19 S11 Ru1 100.06(9)
C12 S11 Ru1 105.24(9)
C16 S17 C18 101.11(13)
C16 S17 Ru1 104.46(8)
C18 S17 Ru1 105.12(9)
O21 S20 C22 106.70(12)
O21 S20 C23 106.27(12)
C22 S20 C23 99.07(12)
O21 S20 Ru1 116.54(8)
C22 S20 Ru1 112.85(10)
C23 S20 Ru1 113.72(10)
F33 P31 F32 91.00(10)
F33 P31 F34 90.06(11)
F32 P31 F34 90.54(9)
F33 P31 F35 178.79(10)
F32 P31 F35 90.16(9)
F34 P31 F35 90.30(11)
F33 P31 F37 90.66(11)
F32 P31 F37 90.05(9)
F34 P31 F37 179.06(11)
F35 P31 F37 88.97(11)
F33 P31 F36 89.19(9)
F32 P31 F36 179.31(10)
F34 P31 F36 90.13(9)
F35 P31 F36 89.66(9)
F37 P31 F36 89.28(9)
N1 O1 Ru1 117.09(12)
C6 N1 C2 122.8(2)
C6 N1 O1 115.68(18)
C2 N1 O1 121.54(19)
C4 C3 C2 121.9(2)
N1 C2 C3 116.6(2)
N1 C2 S2 120.64(18)
C3 C2 S2 122.76(18)
C6 C5 C4 119.7(2)
N1 C6 C5 120.2(2)
C3 C4 C5 118.9(2)
C15 C16 S17 113.20(19)
C12 C13 S14 114.07(16)
C19 C18 S17 111.49(18)
C13 C12 S11 111.64(17)
C16 C15 S14 111.79(17)
C18 C19 S11 113.90(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ru1 O1 2.0857(15)
Ru1 S20 2.2633(7)
Ru1 S17 2.2982(6)
Ru1 S14 2.3278(6)
Ru1 S11 2.3465(7)
Ru1 S2 2.3703(6)
S14 C13 1.824(3)
S14 C15 1.831(2)
S2 C2 1.736(2)
S11 C19 1.823(3)
S11 C12 1.837(2)
S17 C16 1.827(3)
S17 C18 1.843(3)
S20 O21 1.4824(18)
S20 C22 1.770(2)
S20 C23 1.785(2)
P31 F33 1.5873(18)
P31 F32 1.5898(15)
P31 F34 1.5895(19)
P31 F35 1.5938(18)
P31 F37 1.5995(18)
P31 F36 1.6139(14)
O1 N1 1.366(2)
N1 C6 1.358(3)
N1 C2 1.359(3)
C3 C4 1.364(3)
C3 C2 1.404(3)
C5 C6 1.360(3)
C5 C4 1.393(3)
C16 C15 1.520(3)
C13 C12 1.514(4)
C18 C19 1.510(4)
