#------------------------------------------------------------------------------
#$Date: 2016-03-25 13:50:30 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179866 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/62/7016293.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_7016293
loop_
_publ_author_name
'Tan, Caiping'
'Wu, Shouhai'
'Lai, Sensen'
'Wang, Minxu'
'Chen, Yu'
'Zhou, Lingjun'
'Zhu, Yiping'
'Lian, Wu'
'Peng, Wenlie'
'Ji, Liangnian'
'Xu, Anlong'
_publ_section_title
;
 Synthesis, structures, cellular uptake and apoptosis-inducing
 properties of highly cytotoxic ruthenium-Norharman complexes.
;
_journal_issue                   34
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              8611
_journal_page_last               8621
_journal_paper_doi               10.1039/c1dt10084j
_journal_volume                  40
_journal_year                    2011
_chemical_formula_sum            'C58 H48 F6 N8 O6 Ru S2'
_chemical_formula_weight         1232.23
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 119.485(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.372(2)
_cell_length_b                   18.564(2)
_cell_length_c                   16.544(2)
_cell_measurement_temperature    173(2)
_cell_volume                     5446.4(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12793
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.8817
_exptl_absorpt_correction_T_min  0.8385
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.675
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.084
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5295
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      1.200
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0436
_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)+(0.0600P)²+6.8017P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                3900
_reflns_number_total             5295
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1dt10084j.txt
_cod_data_source_block           763615
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        5446.3(11)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7016293
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.5000 0.88634(2) 0.7500 0.02100(14) Uani 1 2 d S . .
N1 N 0.47735(16) 0.80719(15) 0.64830(19) 0.0207(6) Uani 1 1 d . . .
N2 N 0.39323(17) 0.89522(15) 0.7345(2) 0.0235(7) Uani 1 1 d . . .
N3 N 0.51589(16) 0.96697(15) 0.8425(2) 0.0230(7) Uani 1 1 d . . .
N4 N 0.55157(18) 0.64264(17) 0.5978(2) 0.0299(7) Uani 1 1 d . . .
H4B H 0.5879 0.6225 0.6482 0.036 Uiso 1 1 calc R . .
C1 C 0.5218(2) 0.74921(19) 0.6659(3) 0.0248(8) Uani 1 1 d . . .
H1A H 0.5598 0.7393 0.7278 0.030 Uiso 1 1 calc R . .
C2 C 0.5128(2) 0.70380(19) 0.5952(2) 0.0243(8) Uani 1 1 d . . .
C3 C 0.4575(2) 0.71771(19) 0.5023(2) 0.0243(8) Uani 1 1 d . . .
C4 C 0.4104(2) 0.7767(2) 0.4860(3) 0.0273(8) Uani 1 1 d . . .
H4A H 0.3710 0.7872 0.4250 0.033 Uiso 1 1 calc R . .
C5 C 0.4218(2) 0.81893(19) 0.5592(2) 0.0247(8) Uani 1 1 d . . .
H5A H 0.3891 0.8589 0.5474 0.030 Uiso 1 1 calc R . .
C6 C 0.4651(2) 0.6633(2) 0.4461(2) 0.0265(8) Uani 1 1 d . . .
C7 C 0.5240(2) 0.6178(2) 0.5079(3) 0.0276(8) Uani 1 1 d . . .
C8 C 0.5460(2) 0.5584(2) 0.4760(3) 0.0345(9) Uani 1 1 d . . .
H8A H 0.5860 0.5281 0.5175 0.041 Uiso 1 1 calc R . .
C9 C 0.5078(3) 0.5450(2) 0.3823(3) 0.0412(11) Uani 1 1 d . . .
H9A H 0.5209 0.5040 0.3590 0.049 Uiso 1 1 calc R . .
C10 C 0.4502(3) 0.5899(2) 0.3205(3) 0.0397(11) Uani 1 1 d . . .
H10A H 0.4257 0.5793 0.2559 0.048 Uiso 1 1 calc R . .
C11 C 0.4281(2) 0.6497(2) 0.3510(3) 0.0327(9) Uani 1 1 d . . .
H11A H 0.3889 0.6804 0.3086 0.039 Uiso 1 1 calc R . .
C12 C 0.3835(2) 0.9508(2) 0.7807(3) 0.0255(8) Uani 1 1 d . . .
C13 C 0.3149(2) 0.9662(2) 0.7724(3) 0.0387(10) Uani 1 1 d . . .
H13A H 0.3099 1.0059 0.8051 0.046 Uiso 1 1 calc R . .
C14 C 0.2532(2) 0.9243(2) 0.7168(3) 0.0428(11) Uani 1 1 d . . .
H14A H 0.2050 0.9352 0.7095 0.051 Uiso 1 1 calc R . .
C15 C 0.2630(2) 0.8663(2) 0.6720(3) 0.0370(10) Uani 1 1 d . . .
H15A H 0.2218 0.8355 0.6346 0.044 Uiso 1 1 calc R . .
C16 C 0.3330(2) 0.8534(2) 0.6820(3) 0.0265(8) Uani 1 1 d . . .
H16A H 0.3392 0.8133 0.6507 0.032 Uiso 1 1 calc R . .
C17 C 0.4527(2) 0.99181(19) 0.8409(3) 0.0258(8) Uani 1 1 d . . .
C18 C 0.4548(2) 1.0513(2) 0.8938(3) 0.0346(10) Uani 1 1 d . . .
H18A H 0.4098 1.0682 0.8915 0.041 Uiso 1 1 calc R . .
C19 C 0.5224(2) 1.0852(2) 0.9494(3) 0.0391(10) Uani 1 1 d . . .
H19A H 0.5245 1.1263 0.9848 0.047 Uiso 1 1 calc R . .
C20 C 0.5869(2) 1.0589(2) 0.9530(3) 0.0368(10) Uani 1 1 d . . .
H20A H 0.6344 1.0807 0.9922 0.044 Uiso 1 1 calc R . .
C21 C 0.5815(2) 1.0008(2) 0.8989(3) 0.0304(9) Uani 1 1 d . . .
H21A H 0.6263 0.9834 0.9012 0.037 Uiso 1 1 calc R . .
C22 C 0.2609(3) 0.7405(3) 0.1309(3) 0.0580(14) Uani 1 1 d . . .
C23 C 0.2993(4) 0.8038(3) 0.1719(4) 0.0745(18) Uani 1 1 d . . .
H23A H 0.2771 0.8390 0.1926 0.089 Uiso 1 1 calc R . .
C24 C 0.3716(5) 0.8156(4) 0.1825(5) 0.090(2) Uani 1 1 d . . .
H24A H 0.3980 0.8587 0.2109 0.108 Uiso 1 1 calc R . .
C25 C 0.4038(4) 0.7661(5) 0.1528(5) 0.087(2) Uani 1 1 d . . .
H25A H 0.4522 0.7746 0.1594 0.104 Uiso 1 1 calc R . .
C26 C 0.3665(4) 0.7052(4) 0.1141(4) 0.0713(17) Uani 1 1 d . . .
H26A H 0.3893 0.6703 0.0937 0.086 Uiso 1 1 calc R . .
C27 C 0.2956(3) 0.6913(3) 0.1027(3) 0.0617(15) Uani 1 1 d . . .
H27A H 0.2708 0.6473 0.0752 0.074 Uiso 1 1 calc R . .
C28 C 0.1821(3) 0.7272(4) 0.1163(4) 0.086(2) Uani 1 1 d . . .
H28A H 0.1734 0.6753 0.1156 0.129 Uiso 1 1 calc R . .
H28B H 0.1448 0.7483 0.0569 0.129 Uiso 1 1 calc R . .
H28C H 0.1775 0.7496 0.1669 0.129 Uiso 1 1 calc R . .
S1 S 0.28465(5) 0.61531(5) 0.66183(7) 0.0324(2) Uani 1 1 d D . .
O1 O 0.2956(2) 0.69046(19) 0.6706(3) 0.0860(14) Uani 1 1 d . A .
O2 O 0.3196(2) 0.5781(2) 0.7478(2) 0.0712(12) Uani 1 1 d . A .
O3 O 0.21001(16) 0.59022(17) 0.5979(2) 0.0495(9) Uani 1 1 d . A .
C29 C 0.3398(3) 0.5876(4) 0.6125(4) 0.092(2) Uani 0.50 1 d PD A 1
F1 F 0.3266(6) 0.5963(6) 0.5336(5) 0.104(3) Uani 0.50 1 d PDU A 1
F2 F 0.3372(4) 0.5069(3) 0.6153(5) 0.066(2) Uani 0.50 1 d PDU A 1
F3 F 0.4144(3) 0.5940(6) 0.6778(7) 0.078(3) Uani 0.50 1 d PDU A 1
C29' C 0.3398(3) 0.5876(4) 0.6125(4) 0.092(2) Uani 0.50 1 d PD A 2
F1' F 0.3138(6) 0.6439(6) 0.5356(6) 0.135(4) Uani 0.50 1 d PDU A 2
F2' F 0.3258(6) 0.5331(6) 0.5654(8) 0.145(5) Uani 0.50 1 d PDU A 2
F3' F 0.4100(4) 0.6112(8) 0.6554(9) 0.128(6) Uani 0.50 1 d PDU A 2
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N3 Ru1 N3 86.18(16) . 2_656
N3 Ru1 N2 78.72(12) . .
N3 Ru1 N2 94.54(11) 2_656 .
N3 Ru1 N2 94.54(11) . 2_656
N3 Ru1 N2 78.72(12) 2_656 2_656
N2 Ru1 N2 170.85(16) . 2_656
N3 Ru1 N1 176.21(11) . .
N3 Ru1 N1 91.20(11) 2_656 .
N2 Ru1 N1 98.79(11) . .
N2 Ru1 N1 87.62(11) 2_656 .
N3 Ru1 N1 91.20(11) . 2_656
N3 Ru1 N1 176.21(12) 2_656 2_656
N2 Ru1 N1 87.62(11) . 2_656
N2 Ru1 N1 98.79(11) 2_656 2_656
N1 Ru1 N1 91.55(16) . 2_656
C1 N1 C5 118.3(3) . .
C1 N1 Ru1 121.8(2) . .
C5 N1 Ru1 119.4(2) . .
C16 N2 C12 117.5(3) . .
C16 N2 Ru1 127.1(3) . .
C12 N2 Ru1 115.3(2) . .
C21 N3 C17 117.6(3) . .
C21 N3 Ru1 126.4(3) . .
C17 N3 Ru1 115.7(2) . .
C2 N4 C7 108.6(3) . .
C2 N4 H4B 125.7 . .
C7 N4 H4B 125.7 . .
N1 C1 C2 120.8(3) . .
N1 C1 H1A 119.6 . .
C2 C1 H1A 119.6 . .
N4 C2 C1 130.2(3) . .
N4 C2 C3 108.9(3) . .
C1 C2 C3 120.8(3) . .
C4 C3 C2 117.4(3) . .
C4 C3 C6 135.5(3) . .
C2 C3 C6 107.1(3) . .
C5 C4 C3 118.7(3) . .
C5 C4 H4A 120.6 . .
C3 C4 H4A 120.6 . .
C4 C5 N1 123.8(3) . .
C4 C5 H5A 118.1 . .
N1 C5 H5A 118.1 . .
C11 C6 C7 120.3(4) . .
C11 C6 C3 133.6(4) . .
C7 C6 C3 106.1(3) . .
N4 C7 C8 129.6(4) . .
N4 C7 C6 109.3(3) . .
C8 C7 C6 121.2(4) . .
C9 C8 C7 117.6(4) . .
C9 C8 H8A 121.2 . .
C7 C8 H8A 121.2 . .
C8 C9 C10 121.8(4) . .
C8 C9 H9A 119.1 . .
C10 C9 H9A 119.1 . .
C11 C10 C9 121.4(4) . .
C11 C10 H10A 119.3 . .
C9 C10 H10A 119.3 . .
C10 C11 C6 117.7(4) . .
C10 C11 H11A 121.1 . .
C6 C11 H11A 121.1 . .
N2 C12 C13 122.0(4) . .
N2 C12 C17 114.6(3) . .
C13 C12 C17 123.4(4) . .
C12 C13 C14 120.2(4) . .
C12 C13 H13A 119.9 . .
C14 C13 H13A 119.9 . .
C13 C14 C15 118.3(4) . .
C13 C14 H14A 120.8 . .
C15 C14 H14A 120.8 . .
C16 C15 C14 119.3(4) . .
C16 C15 H15A 120.4 . .
C14 C15 H15A 120.4 . .
N2 C16 C15 122.7(4) . .
N2 C16 H16A 118.7 . .
C15 C16 H16A 118.7 . .
N3 C17 C18 121.4(3) . .
N3 C17 C12 114.9(3) . .
C18 C17 C12 123.7(3) . .
C19 C18 C17 119.4(4) . .
C19 C18 H18A 120.3 . .
C17 C18 H18A 120.3 . .
C18 C19 C20 119.3(4) . .
C18 C19 H19A 120.4 . .
C20 C19 H19A 120.4 . .
C21 C20 C19 118.9(4) . .
C21 C20 H20A 120.6 . .
C19 C20 H20A 120.6 . .
N3 C21 C20 123.4(4) . .
N3 C21 H21A 118.3 . .
C20 C21 H21A 118.3 . .
C27 C22 C23 117.9(6) . .
C27 C22 C28 121.2(6) . .
C23 C22 C28 120.8(6) . .
C22 C23 C24 119.6(6) . .
C22 C23 H23A 120.2 . .
C24 C23 H23A 120.2 . .
C25 C24 C23 120.9(7) . .
C25 C24 H24A 119.6 . .
C23 C24 H24A 119.6 . .
C26 C25 C24 119.0(7) . .
C26 C25 H25A 120.5 . .
C24 C25 H25A 120.5 . .
C25 C26 C27 122.0(6) . .
C25 C26 H26A 119.0 . .
C27 C26 H26A 119.0 . .
C22 C27 C26 120.6(6) . .
C22 C27 H27A 119.7 . .
C26 C27 H27A 119.7 . .
C22 C28 H28A 109.5 . .
C22 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C22 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O1 S1 O2 113.8(3) . .
O1 S1 O3 116.9(2) . .
O2 S1 O3 114.0(2) . .
O1 S1 C29 103.5(3) . .
O2 S1 C29 101.7(3) . .
O3 S1 C29 104.4(2) . .
F1 C29 F3 114.2(8) . .
F1 C29 F2 100.0(6) . .
F3 C29 F2 96.0(6) . .
F1 C29 S1 127.6(6) . .
F3 C29 S1 108.9(5) . .
F2 C29 S1 103.8(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 N3 2.049(3) .
Ru1 N3 2.049(3) 2_656
Ru1 N2 2.067(3) .
Ru1 N2 2.067(3) 2_656
Ru1 N1 2.107(3) .
Ru1 N1 2.107(3) 2_656
N1 C1 1.342(4) .
N1 C5 1.364(4) .
N2 C16 1.346(5) .
N2 C12 1.355(5) .
N3 C21 1.351(5) .
N3 C17 1.354(5) .
N4 C2 1.371(5) .
N4 C7 1.384(5) .
N4 H4B 0.8800 .
C1 C2 1.380(5) .
C1 H1A 0.9500 .
C2 C3 1.412(5) .
C3 C4 1.391(5) .
C3 C6 1.432(5) .
C4 C5 1.363(5) .
C4 H4A 0.9500 .
C5 H5A 0.9500 .
C6 C11 1.392(5) .
C6 C7 1.412(5) .
C7 C8 1.389(5) .
C8 C9 1.372(6) .
C8 H8A 0.9500 .
C9 C10 1.391(6) .
C9 H9A 0.9500 .
C10 C11 1.385(6) .
C10 H10A 0.9500 .
C11 H11A 0.9500 .
C12 C13 1.365(5) .
C12 C17 1.476(5) .
C13 C14 1.377(6) .
C13 H13A 0.9500 .
C14 C15 1.377(6) .
C14 H14A 0.9500 .
C15 C16 1.374(6) .
C15 H15A 0.9500 .
C16 H16A 0.9500 .
C17 C18 1.398(5) .
C18 C19 1.375(6) .
C18 H18A 0.9500 .
C19 C20 1.376(6) .
C19 H19A 0.9500 .
C20 C21 1.371(5) .
C20 H20A 0.9500 .
C21 H21A 0.9500 .
C22 C27 1.368(7) .
C22 C23 1.390(8) .
C22 C28 1.520(8) .
C23 C24 1.411(9) .
C23 H23A 0.9500 .
C24 C25 1.353(10) .
C24 H24A 0.9500 .
C25 C26 1.338(9) .
C25 H25A 0.9500 .
C26 C27 1.387(8) .
C26 H26A 0.9500 .
C27 H27A 0.9500 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
S1 O1 1.409(4) .
S1 O2 1.419(3) .
S1 O3 1.437(3) .
S1 C29 1.758(6) .
C29 F1 1.208(7) .
C29 F3 1.369(8) .
C29 F2 1.499(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N4 H4B O2 0.88 2.00 2.872(4) 170.6 2_656
N4 H4B S1 0.88 2.93 3.761(3) 157.3 2_656
