#------------------------------------------------------------------------------
#$Date: 2016-02-15 15:17:41 +0200 (Mon, 15 Feb 2016) $
#$Revision: 176446 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/64/4086403.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_4086403
loop_
_publ_author_name
'Wu, Qiong'
'Zheng, Kangdi'
'Liao, Siyan'
'Ding, Yang'
'Li, Yangqiu'
'Mei, Wenjie'
_publ_section_title
;
 Arene Ruthenium(II) Complexes as Low-Toxicity Inhibitor against the
 Proliferation, Migration, and Invasion of MDA-MB-231 Cells through
 Binding and Stabilizing c-myc G-Quadruplex DNA
;
_journal_name_full               Organometallics
_journal_page_first              317
_journal_page_last               326
_journal_paper_doi               10.1021/acs.organomet.5b00820
_journal_volume                  35
_journal_year                    2016
_chemical_formula_sum            'C25 H23 Cl3 N4 O3 Ru'
_chemical_formula_weight         634.89
_chemical_name_systematic
; 
 ? 
;
_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                 90.996(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   42.2839(12)
_cell_length_b                   17.4919(7)
_cell_length_c                   7.5827(2)
_cell_measurement_temperature    293(2)
_cell_volume                     5607.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8854
_diffrn_reflns_theta_full        62.71
_diffrn_reflns_theta_max         62.71
_diffrn_reflns_theta_min         5.06
_exptl_absorpt_coefficient_mu    7.431
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2560
_refine_diff_density_max         1.261
_refine_diff_density_min         -1.088
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       0.00010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         4414
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0616
_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)+(0.1220P)²+3.2506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1658
_refine_ls_wR_factor_ref         0.1793
_reflns_number_gt                3752
_reflns_number_total             4414
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00820_si_002.cif
_cod_data_source_block           sad
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4086403
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 0.064202(8) 0.33577(2) 0.98055(5) 0.0426(2) Uani 1 1 d . . .
Cl1 Cl 0.06088(3) 0.39142(9) 0.69209(17) 0.0567(4) Uani 1 1 d . . .
Cl2 Cl 0.36337(4) 0.18862(13) 0.5981(2) 0.0756(5) Uani 1 1 d . . .
N1 N 0.09259(10) 0.2530(3) 0.8647(6) 0.0478(11) Uani 1 1 d . . .
C1 C 0.05651(18) 0.3609(8) 1.2551(10) 0.093(3) Uani 1 1 d . . .
H1A H 0.0734 0.3844 1.3265 0.112 Uiso 1 1 calc R . .
O1 O 0.0000 0.1228(4) 0.7500 0.115(3) Uani 1 2 d S . .
H10B H 0.0207 0.1067 0.7149 0.172 Uiso 0.50 1 d PR . .
H10C H -0.0081 0.0874 0.8347 0.172 Uiso 0.50 1 d PR . .
N2 N 0.10890(9) 0.3869(2) 0.9958(5) 0.0410(10) Uani 1 1 d . . .
C2 C 0.0360(2) 0.4072(5) 1.1539(13) 0.097(3) Uani 1 1 d . . .
H2A H 0.0388 0.4628 1.1537 0.117 Uiso 1 1 calc R . .
O2 O 0.2936(4) 0.5412(9) 0.752(4) 0.154(9) Uani 0.50 1 d P A 1
H20B H 0.3021 0.4915 0.7270 0.231 Uiso 0.50 1 d PR A 1
H20C H 0.2851 0.5416 0.8682 0.231 Uiso 0.50 1 d PR A 1
O2A O 0.2969(5) 0.5461(11) 0.912(3) 0.148(8) Uani 0.50 1 d P B 2
H20E H 0.2819 0.5707 0.8337 0.221 Uiso 0.50 1 d PR B 2
H20G H 0.2874 0.5378 1.0242 0.221 Uiso 0.50 1 d PR B 2
N3 N 0.20569(10) 0.2094(3) 0.7475(6) 0.0474(10) Uani 1 1 d . . .
C3 C 0.01574(15) 0.3722(7) 1.0255(11) 0.085(3) Uani 1 1 d . . .
H3A H 0.0049 0.4042 0.9372 0.102 Uiso 1 1 calc R . .
O3 O 0.3519(8) 0.5308(19) 1.153(8) 0.55(5) Uani 0.50 1 d P . .
H30D H 0.3373 0.5499 1.0654 0.659 Uiso 0.50 1 d PR . .
H30A H 0.3697 0.5647 1.1629 0.824 Uiso 0.50 1 d PR . .
N4 N 0.21905(10) 0.3247(3) 0.8460(6) 0.0439(10) Uani 1 1 d . . .
H4B H 0.2302 0.3642 0.8740 0.053 Uiso 1 1 calc R . .
C4 C 0.01513(16) 0.2955(7) 1.0067(10) 0.084(3) Uani 1 1 d . . .
H4A H 0.0040 0.2725 0.9054 0.101 Uiso 1 1 calc R . .
O4 O 0.4063(11) 0.4104(9) 0.801(2) 0.33(3) Uani 0.50 1 d P . .
H40A H 0.4160 0.4548 0.8531 0.492 Uiso 0.50 1 d PR . .
H40B H 0.3976 0.4236 0.6867 0.492 Uiso 0.50 1 d PR . .
C5 C 0.0349(2) 0.2517(5) 1.1108(15) 0.094(3) Uani 1 1 d . . .
H5A H 0.0377 0.1980 1.0776 0.113 Uiso 1 1 calc R . .
O5 O 0.0388(17) 0.056(4) 0.494(10) 0.50(4) Uiso 0.50 1 d P . .
H50D H 0.0456 0.0583 0.6150 0.743 Uiso 0.50 1 d PR . .
H50C H 0.0569 0.0615 0.4193 0.743 Uiso 0.50 1 d PR . .
C6 C 0.0553(2) 0.2812(9) 1.2362(13) 0.106(4) Uani 1 1 d . . .
H6A H 0.0715 0.2487 1.2926 0.127 Uiso 1 1 calc R . .
C7 C 0.08291(15) 0.1888(4) 0.7912(11) 0.0687(18) Uani 1 1 d . . .
H7A H 0.0614 0.1776 0.7888 0.082 Uiso 1 1 calc R . .
C8 C 0.10415(17) 0.1365(5) 0.7160(12) 0.084(2) Uani 1 1 d . . .
H8A H 0.0965 0.0920 0.6633 0.101 Uiso 1 1 calc R . .
C9 C 0.13564(15) 0.1507(4) 0.7201(10) 0.0629(17) Uani 1 1 d . . .
H9A H 0.1497 0.1157 0.6734 0.075 Uiso 1 1 calc R . .
C10 C 0.14666(12) 0.2189(3) 0.7955(7) 0.0475(12) Uani 1 1 d . . .
C11 C 0.12432(11) 0.2698(3) 0.8649(7) 0.0421(11) Uani 1 1 d . . .
C12 C 0.13273(12) 0.3422(3) 0.9326(6) 0.0378(11) Uani 1 1 d . . .
C13 C 0.16448(11) 0.3683(3) 0.9349(6) 0.0396(11) Uani 1 1 d . . .
C14 C 0.17097(12) 0.4412(3) 1.0031(7) 0.0478(12) Uani 1 1 d . . .
H14A H 0.1915 0.4600 1.0086 0.057 Uiso 1 1 calc R . .
C15 C 0.14583(13) 0.4845(3) 1.0621(8) 0.0526(13) Uani 1 1 d . . .
H15A H 0.1495 0.5332 1.1068 0.063 Uiso 1 1 calc R . .
C16 C 0.11555(12) 0.4562(3) 1.0555(7) 0.0478(12) Uani 1 1 d . . .
H16A H 0.0991 0.4869 1.0943 0.057 Uiso 1 1 calc R . .
C17 C 0.18706(12) 0.3159(3) 0.8641(7) 0.0427(11) Uani 1 1 d . . .
C18 C 0.17868(12) 0.2451(3) 0.8036(7) 0.0453(12) Uani 1 1 d . . .
C19 C 0.22938(12) 0.2590(3) 0.7754(7) 0.0467(12) Uani 1 1 d . . .
C20 C 0.26266(12) 0.2426(3) 0.7320(7) 0.0489(13) Uani 1 1 d . . .
C21 C 0.27007(14) 0.1741(4) 0.6576(9) 0.0553(15) Uani 1 1 d . . .
H21A H 0.2544 0.1379 0.6358 0.066 Uiso 1 1 calc R . .
C22 C 0.30178(15) 0.1583(4) 0.6137(10) 0.0625(17) Uani 1 1 d . . .
H22A H 0.3070 0.1121 0.5608 0.075 Uiso 1 1 calc R . .
C23 C 0.32424(13) 0.2103(4) 0.6486(8) 0.0580(16) Uani 1 1 d . . .
C24 C 0.31751(14) 0.2799(4) 0.7237(9) 0.0620(15) Uani 1 1 d . . .
H24A H 0.3335 0.3154 0.7458 0.074 Uiso 1 1 calc R . .
C25 C 0.28632(14) 0.2961(4) 0.7657(9) 0.0585(15) Uani 1 1 d . . .
H25A H 0.2813 0.3429 0.8164 0.070 Uiso 1 1 calc R . .
Cl3 Cl 0.2495(3) 0.4694(6) 0.934(3) 0.257(8) Uani 0.50 1 d P C 1
Cl3A Cl 0.2338(6) 0.4727(13) 0.729(4) 0.374(14) Uani 0.50 1 d P D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru 0.0552 3.2960 '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
N1 Ru1 N2 78.12(16) . .
N1 Ru1 C1 130.2(4) . .
N2 Ru1 C1 90.6(2) . .
N1 Ru1 C5 93.4(3) . .
N2 Ru1 C5 141.8(3) . .
C1 Ru1 C5 66.6(4) . .
N1 Ru1 C3 145.0(3) . .
N2 Ru1 C3 135.8(3) . .
C1 Ru1 C3 68.4(3) . .
C5 Ru1 C3 65.3(4) . .
N1 Ru1 C2 167.4(3) . .
N2 Ru1 C2 103.0(3) . .
C1 Ru1 C2 37.8(4) . .
C5 Ru1 C2 78.0(4) . .
C3 Ru1 C2 38.1(4) . .
N1 Ru1 C6 100.3(4) . .
N2 Ru1 C6 107.7(3) . .
C1 Ru1 C6 37.5(4) . .
C5 Ru1 C6 36.6(4) . .
C3 Ru1 C6 79.3(3) . .
C2 Ru1 C6 67.3(4) . .
N1 Ru1 C4 111.5(3) . .
N2 Ru1 C4 169.3(3) . .
C1 Ru1 C4 79.6(3) . .
C5 Ru1 C4 36.6(4) . .
C3 Ru1 C4 35.9(4) . .
C2 Ru1 C4 66.6(4) . .
C6 Ru1 C4 66.8(4) . .
N1 Ru1 Cl1 85.54(13) . .
N2 Ru1 Cl1 85.14(11) . .
C1 Ru1 Cl1 142.2(4) . .
C5 Ru1 Cl1 131.7(3) . .
C3 Ru1 Cl1 89.1(2) . .
C2 Ru1 Cl1 107.0(3) . .
C6 Ru1 Cl1 166.7(3) . .
C4 Ru1 Cl1 99.9(2) . .
C7 N1 C11 118.7(5) . .
C7 N1 Ru1 126.4(4) . .
C11 N1 Ru1 114.8(4) . .
C6 C1 C2 119.8(8) . .
C6 C1 Ru1 72.8(5) . .
C2 C1 Ru1 72.1(4) . .
C16 N2 C12 119.4(4) . .
C16 N2 Ru1 126.7(3) . .
C12 N2 Ru1 113.9(3) . .
C1 C2 C3 118.9(9) . .
C1 C2 Ru1 70.1(4) . .
C3 C2 Ru1 70.7(4) . .
C19 N3 C18 106.3(5) . .
C4 C3 C2 120.7(8) . .
C4 C3 Ru1 73.1(4) . .
C2 C3 Ru1 71.2(4) . .
C19 N4 C17 105.7(4) . .
C3 C4 C5 118.9(8) . .
C3 C4 Ru1 71.1(4) . .
C5 C4 Ru1 70.4(4) . .
C6 C5 C4 123.9(10) . .
C6 C5 Ru1 72.8(5) . .
C4 C5 Ru1 73.0(4) . .
C5 C6 C1 117.7(8) . .
C5 C6 Ru1 70.6(4) . .
C1 C6 Ru1 69.6(4) . .
N1 C7 C8 122.0(6) . .
C9 C8 C7 120.3(7) . .
C8 C9 C10 119.1(6) . .
C9 C10 C11 118.1(5) . .
C9 C10 C18 126.8(5) . .
C11 C10 C18 115.0(5) . .
N1 C11 C12 115.7(5) . .
N1 C11 C10 121.7(5) . .
C12 C11 C10 122.6(5) . .
N2 C12 C11 117.3(5) . .
N2 C12 C13 121.0(4) . .
C11 C12 C13 121.8(4) . .
C14 C13 C12 118.5(4) . .
C14 C13 C17 126.3(5) . .
C12 C13 C17 115.2(4) . .
C15 C14 C13 118.0(5) . .
C16 C15 C14 120.8(5) . .
N2 C16 C15 122.4(5) . .
C18 C17 N4 108.6(4) . .
C18 C17 C13 122.3(5) . .
N4 C17 C13 129.0(5) . .
C17 C18 N3 107.6(5) . .
C17 C18 C10 123.0(5) . .
N3 C18 C10 129.3(5) . .
N3 C19 N4 111.7(4) . .
N3 C19 C20 123.5(5) . .
N4 C19 C20 124.8(5) . .
C21 C20 C25 119.9(5) . .
C21 C20 C19 119.3(6) . .
C25 C20 C19 120.9(5) . .
C20 C21 C22 119.6(6) . .
C23 C22 C21 119.6(6) . .
C22 C23 C24 122.2(5) . .
C22 C23 Cl2 118.8(5) . .
C24 C23 Cl2 119.1(5) . .
C23 C24 C25 118.6(6) . .
C20 C25 C24 120.2(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 N1 2.085(5) .
Ru1 N2 2.093(4) .
Ru1 C1 2.158(7) .
Ru1 C5 2.170(7) .
Ru1 C3 2.179(6) .
Ru1 C2 2.184(7) .
Ru1 C6 2.199(7) .
Ru1 C4 2.204(6) .
Ru1 Cl1 2.3960(13) .
Cl2 C23 1.746(5) .
N1 C7 1.315(8) .
N1 C11 1.373(6) .
C1 C6 1.402(16) .
C1 C2 1.406(14) .
N2 C16 1.322(7) .
N2 C12 1.369(6) .
C2 C3 1.424(13) .
N3 C19 1.338(7) .
N3 C18 1.375(6) .
C3 C4 1.349(14) .
N4 C19 1.345(7) .
N4 C17 1.371(7) .
C4 C5 1.374(14) .
C5 C6 1.374(16) .
C7 C8 1.410(10) .
C8 C9 1.354(9) .
C9 C10 1.398(8) .
C10 C11 1.408(7) .
C10 C18 1.430(8) .
C11 C12 1.409(7) .
C12 C13 1.418(7) .
C13 C14 1.402(7) .
C13 C17 1.434(7) .
C14 C15 1.385(8) .
C15 C16 1.373(8) .
C17 C18 1.366(8) .
C19 C20 1.479(7) .
C20 C21 1.364(9) .
C20 C25 1.391(9) .
C21 C22 1.414(8) .
C22 C23 1.338(10) .
C23 C24 1.377(10) .
C24 C25 1.392(8) .
