#------------------------------------------------------------------------------
#$Date: 2018-09-03 19:38:49 +0300 (Mon, 03 Sep 2018) $
#$Revision: 210357 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/95/7039593.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_7039593
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 O3 Ru S4, F6 P, 0.5(C H Cl3)'
_chemical_formula_sum            'C13.5 H22.5 Cl1.5 F6 N O3 P Ru S4'
_chemical_formula_weight         674.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.7623(4)
_cell_length_b                   21.1882(3)
_cell_length_c                   7.78650(10)
_cell_measurement_reflns_used    2529
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.1577
_cell_measurement_theta_min      2.4588
_cell_volume                     4745.26(11)
_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 0.998
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            47625
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         2.876
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  1.1069
_exptl_absorpt_correction_T_min  0.8880
_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    1.888
_exptl_crystal_description       needle
_exptl_crystal_F_000             2696
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.679
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.679
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0503P)²+14.6208P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0662
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4862
_reflns_number_total             5583
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6dt00668j2.cif
_cod_data_source_block           mo131
_cod_depositor_comments
;
Adding full bibliography for 7039593--7039596.cif.

2018-07-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C27 H45 Cl3 F12 N2 O6 P2 Ru2 S8'
_cod_original_formula_weight         1348.56
_cod_original_formula_moiety         '2(C13 H22 N O3 Ru S4), 2(F6 P), C H Cl3'
_cod_original_formula_units_Z            4
_cod_database_code               7039593
_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   0.694
_shelx_estimated_absorpt_t_max   0.914
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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
_atom_site_refinement_flags_occupancy
Ru1 Ru 0.12519(2) 0.50871(2) 0.36499(2) 0.01378(5) Uani 1 1 d . . .
S14 S 0.13208(2) 0.41810(3) 0.52299(7) 0.01803(11) Uani 1 1 d . . .
S11 S 0.20099(2) 0.49516(2) 0.28228(7) 0.01798(11) Uani 1 1 d . . .
P40 P 0.16977(3) 0.2500 -0.13675(11) 0.02170(17) Uani 1 2 d S T P
S17 S 0.10225(2) 0.44716(3) 0.12995(7) 0.02249(12) Uani 1 1 d . . .
S20 S 0.14556(2) 0.56779(3) 0.59456(7) 0.01985(11) Uani 1 1 d . . .
P31 P -0.02018(3) 0.2500 -0.61677(11) 0.02369(17) Uani 1 2 d S T P
Cl52 Cl 0.25749(3) 0.2500 0.33611(12) 0.0362(2) Uani 1 2 d S T P
Cl51 Cl 0.31731(2) 0.31807(3) 0.57345(9) 0.03746(15) Uani 1 1 d . . .
F41 F 0.20910(5) 0.30327(7) -0.1260(2) 0.0391(4) Uani 1 1 d . . .
F44 F 0.13081(5) 0.30309(7) -0.1511(2) 0.0383(4) Uani 1 1 d . . .
F36 F 0.02002(8) 0.2500 -0.4764(3) 0.0424(6) Uani 1 2 d S T P
F42 F 0.16504(8) 0.2500 0.0672(3) 0.0433(6) Uani 1 2 d S T P
C12 C 0.21971(8) 0.41939(11) 0.3738(3) 0.0253(5) Uani 1 1 d . . .
H12A H 0.2133 0.3852 0.2904 0.030 Uiso 1 1 calc R U .
H12B H 0.2537 0.4205 0.3947 0.030 Uiso 1 1 calc R U .
O1 O 0.05496(5) 0.52198(8) 0.4166(2) 0.0218(3) Uani 1 1 d . . .
O2 O 0.11187(5) 0.58875(7) 0.21432(19) 0.0195(3) Uani 1 1 d . . .
F34 F -0.01989(6) 0.32540(7) -0.6183(2) 0.0468(4) Uani 1 1 d . . .
F32 F 0.01914(8) 0.2500 -0.7638(3) 0.0414(5) Uani 1 2 d S T P
C18 C 0.15695(9) 0.42482(12) 0.0273(3) 0.0305(5) Uani 1 1 d . . .
H18A H 0.1672 0.3835 0.0729 0.037 Uiso 1 1 calc R U .
H18B H 0.1519 0.4201 -0.0978 0.037 Uiso 1 1 calc R U .
C2 C 0.06662(7) 0.60149(9) 0.2139(2) 0.0144(4) Uani 1 1 d . . .
F43 F 0.17505(9) 0.2500 -0.3424(3) 0.0417(5) Uani 1 2 d S T P
C19 C 0.19445(9) 0.47301(12) 0.0577(3) 0.0283(5) Uani 1 1 d . . .
H19A H 0.1873 0.5113 -0.0102 0.034 Uiso 1 1 calc R U .
H19B H 0.2244 0.4559 0.0155 0.034 Uiso 1 1 calc R U .
C15 C 0.11570(9) 0.35271(11) 0.3786(3) 0.0283(5) Uani 1 1 d . . .
H15A H 0.1442 0.3339 0.3290 0.034 Uiso 1 1 calc R U .
H15B H 0.0996 0.3196 0.4459 0.034 Uiso 1 1 calc R U .
C3 C 0.04833(8) 0.64942(11) 0.1121(3) 0.0225(4) Uani 1 1 d . . .
H3 H 0.0684 0.6744 0.0431 0.027 Uiso 1 1 calc R U .
O21 O 0.18810(6) 0.54777(9) 0.6884(2) 0.0299(4) Uani 1 1 d . . .
N1 N 0.03762(6) 0.56758(9) 0.3143(2) 0.0228(4) Uani 1 1 d . . .
C22 C 0.10013(9) 0.57147(15) 0.7495(3) 0.0363(6) Uani 1 1 d . . .
H22A H 0.0915 0.5286 0.7843 0.054 Uiso 1 1 calc R U .
H22B H 0.0731 0.5927 0.6993 0.054 Uiso 1 1 calc R U .
H22C H 0.1108 0.5952 0.8501 0.054 Uiso 1 1 calc R U .
C13 C 0.19492(7) 0.40544(11) 0.5395(3) 0.0241(5) Uani 1 1 d . . .
H13A H 0.2076 0.4329 0.6311 0.029 Uiso 1 1 calc R U .
H13B H 0.2009 0.3611 0.5726 0.029 Uiso 1 1 calc R U .
C5 C -0.02798(8) 0.62475(12) 0.2145(3) 0.0265(5) Uani 1 1 d . . .
H5 H -0.0605 0.6326 0.2145 0.032 Uiso 1 1 calc R U .
F33 F -0.05994(9) 0.2500 -0.7602(3) 0.0500(6) Uani 1 2 d S T P
C50 C 0.28310(12) 0.2500 0.5423(5) 0.0272(7) Uani 1 2 d S T P
H50 H 0.2577 0.2500 0.6298 0.033 Uiso 1 2 calc R U P
F35 F -0.05869(8) 0.2500 -0.4711(3) 0.0529(7) Uani 1 2 d S T P
C16 C 0.08415(9) 0.37449(12) 0.2344(3) 0.0316(5) Uani 1 1 d . . .
H16A H 0.0524 0.3805 0.2810 0.038 Uiso 1 1 calc R U .
H16B H 0.0825 0.3407 0.1468 0.038 Uiso 1 1 calc R U .
C6 C -0.00979(7) 0.57846(11) 0.3153(3) 0.0219(4) Uani 1 1 d . . .
H6 H -0.0296 0.5537 0.3861 0.026 Uiso 1 1 calc R U .
C4 C 0.00174(8) 0.66071(11) 0.1108(3) 0.0268(5) Uani 1 1 d . . .
H4 H -0.0106 0.6930 0.0396 0.032 Uiso 1 1 calc R U .
C23 C 0.15195(11) 0.64927(12) 0.5461(4) 0.0399(7) Uani 1 1 d . . .
H23A H 0.1572 0.6729 0.6525 0.060 Uiso 1 1 calc R U .
H23B H 0.1236 0.6647 0.4901 0.060 Uiso 1 1 calc R U .
H23C H 0.1785 0.6551 0.4689 0.060 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'
Cl Cl 0.1484 0.1585 '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
O1 Ru1 O2 79.71(6) . .
O1 Ru1 S20 91.38(5) . .
O2 Ru1 S20 92.40(5) . .
O1 Ru1 S14 95.37(4) . .
O2 Ru1 S14 174.10(4) . .
S20 Ru1 S14 90.97(2) . .
O1 Ru1 S11 174.82(4) . .
O2 Ru1 S11 96.77(4) . .
S20 Ru1 S11 92.58(2) . .
S14 Ru1 S11 87.916(19) . .
O1 Ru1 S17 87.29(5) . .
O2 Ru1 S17 87.81(4) . .
S20 Ru1 S17 178.59(2) . .
S14 Ru1 S17 88.70(2) . .
S11 Ru1 S17 88.78(2) . .
C13 S14 C15 100.65(12) . .
C13 S14 Ru1 104.24(7) . .
C15 S14 Ru1 106.28(8) . .
C19 S11 C12 100.23(12) . .
C19 S11 Ru1 101.78(8) . .
C12 S11 Ru1 106.22(7) . .
F42 P40 F44 90.57(10) . .
F42 P40 F44 90.57(10) . 8_565
F44 P40 F44 89.94(12) . 8_565
F42 P40 F41 90.46(9) . 8_565
F44 P40 F41 178.96(11) . 8_565
F44 P40 F41 90.16(8) 8_565 8_565
F42 P40 F41 90.46(9) . .
F44 P40 F41 90.16(8) . .
F44 P40 F41 178.96(11) 8_565 .
F41 P40 F41 89.72(13) 8_565 .
F42 P40 F43 179.48(14) . .
F44 P40 F43 89.80(10) . .
F44 P40 F43 89.80(10) 8_565 .
F41 P40 F43 89.17(10) 8_565 .
F41 P40 F43 89.17(10) . .
C16 S17 C18 102.88(13) . .
C16 S17 Ru1 101.71(8) . .
C18 S17 Ru1 104.10(8) . .
O21 S20 C23 107.25(13) . .
O21 S20 C22 106.47(11) . .
C23 S20 C22 100.21(15) . .
O21 S20 Ru1 116.37(7) . .
C23 S20 Ru1 113.39(9) . .
C22 S20 Ru1 111.71(9) . .
F35 P31 F36 90.93(14) . .
F35 P31 F34 90.52(7) . 8_565
F36 P31 F34 90.08(7) . 8_565
F35 P31 F34 90.52(7) . .
F36 P31 F34 90.08(7) . .
F34 P31 F34 178.95(16) 8_565 .
F35 P31 F33 90.01(15) . .
F36 P31 F33 179.06(15) . .
F34 P31 F33 89.91(7) 8_565 .
F34 P31 F33 89.91(7) . .
F35 P31 F32 179.67(14) . .
F36 P31 F32 88.73(13) . .
F34 P31 F32 89.48(7) 8_565 .
F34 P31 F32 89.48(7) . .
F33 P31 F32 90.32(14) . .
C13 C12 S11 111.45(16) . .
N1 O1 Ru1 110.01(12) . .
C2 O2 Ru1 110.15(12) . .
C19 C18 S17 111.89(17) . .
O2 C2 N1 119.69(18) . .
O2 C2 C3 121.32(19) . .
N1 C2 C3 118.98(19) . .
C18 C19 S11 113.59(16) . .
C16 C15 S14 112.06(17) . .
C4 C3 C2 120.3(2) . .
O1 N1 C2 119.66(17) . .
O1 N1 C6 118.75(18) . .
C2 N1 C6 121.58(19) . .
C12 C13 S14 112.25(15) . .
C6 C5 C4 119.3(2) . .
Cl51 C50 Cl51 109.81(18) 8_565 .
Cl51 C50 Cl52 110.98(14) 8_565 .
Cl51 C50 Cl52 110.98(14) . .
C15 C16 S17 114.70(17) . .
C5 C6 N1 119.7(2) . .
C3 C4 C5 120.1(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 O1 2.0786(15) .
Ru1 O2 2.0974(15) .
Ru1 S20 2.2596(5) .
Ru1 S14 2.2888(5) .
Ru1 S11 2.2913(5) .
Ru1 S17 2.3421(5) .
S14 C13 1.832(2) .
S14 C15 1.845(2) .
S11 C19 1.821(2) .
S11 C12 1.837(2) .
P40 F42 1.594(2) .
P40 F44 1.5917(15) .
P40 F44 1.5918(15) 8_565
P40 F41 1.6003(16) 8_565
P40 F41 1.6003(16) .
P40 F43 1.608(2) .
S17 C16 1.817(2) .
S17 C18 1.827(3) .
S20 O21 1.4870(16) .
S20 C23 1.777(3) .
S20 C22 1.780(3) .
P31 F35 1.585(2) .
P31 F36 1.591(2) .
P31 F34 1.5976(16) 8_565
P31 F34 1.5976(16) .
P31 F33 1.598(2) .
P31 F32 1.610(2) .
Cl52 C50 1.766(4) .
Cl51 C50 1.763(2) .
C12 C13 1.504(3) .
O1 N1 1.348(2) .
O2 C2 1.329(2) .
C18 C19 1.504(4) .
C2 N1 1.351(3) .
C2 C3 1.392(3) .
C15 C16 1.516(3) .
C3 C4 1.361(3) .
N1 C6 1.383(3) .
C5 C6 1.361(3) .
C5 C4 1.401(3) .
C50 Cl51 1.763(2) 8_565
