#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:05:55 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178710 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/21/4082150.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_4082150
loop_
_publ_author_name
'Belsa, Lluís'
'López, Concepción'
'González, Asensio'
'Font-Bard\?ía, Mercè'
'Calvet, Teresa'
'Calvis, Carmen'
'Messeguer, Ramon'
_publ_section_title
;
 Neutral and Ionic Cycloruthenated 2-Phenylindoles as Cytotoxic Agents
;
_journal_issue                   24
_journal_name_full               Organometallics
_journal_page_first              7264
_journal_paper_doi               10.1021/om400941b
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C26 H27 Cl N2 O2 Ru H2 O'
_chemical_formula_sum            'C26 H29 Cl N2 O3 Ru'
_chemical_formula_weight         554.03
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           148
_symmetry_cell_setting           trigonal
_symmetry_space_group_name_Hall  '-R 3'
_symmetry_space_group_name_H-M   'R -3 :H'
_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                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            18
_cell_length_a                   28.202(4)
_cell_length_b                   28.202(4)
_cell_length_c                   16.5790(10)
_cell_measurement_reflns_used    583
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     11420(2)
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_collection       'MARXDS (Claudio Klein, 2005)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.772
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'phi scan'
_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  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            33147
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.13
_diffrn_reflns_theta_min         1.44
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             5112
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.100
_refine_diff_density_min         -1.386
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         6878
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.168
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0626
_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)+(0.0814P)²+29.6169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1743
_refine_ls_wR_factor_ref         0.1791
_reflns_number_gt                6207
_reflns_number_total             6878
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400941b_si_002.cif
_cod_data_source_block           chpm33a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Trigonal' changed to 'trigonal'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      R-3
_cod_database_code               4082150
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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
Ru1 Ru 0.612046(12) 0.058110(13) 0.589844(17) 0.05357(13) Uani 1 1 d U
Cl1 Cl 0.60420(4) 0.00903(5) 0.46728(6) 0.0646(2) Uani 1 1 d U
O1 O 0.86742(14) 0.20545(15) 0.4961(2) 0.0850(10) Uani 1 1 d .
O2 O 0.86813(14) 0.06682(17) 0.6777(3) 0.0891(11) Uani 1 1 d .
N1 N 0.69629(14) 0.09403(15) 0.5783(2) 0.0627(8) Uani 1 1 d U
N2 N 0.81524(18) 0.19881(17) 0.4911(3) 0.0787(11) Uani 1 1 d .
C1 C 0.5511(2) -0.0217(2) 0.6547(3) 0.0790(13) Uani 1 1 d U
C2 C 0.5248(2) 0.0045(3) 0.6196(3) 0.0793(13) Uani 1 1 d .
H2 H 0.4969 -0.0143 0.5823 0.095 Uiso 1 1 calc R
C3 C 0.5395(2) 0.0563(3) 0.6393(3) 0.0802(14) Uani 1 1 d .
H3 H 0.5185 0.0708 0.6198 0.096 Uiso 1 1 calc R
C4 C 0.5863(2) 0.0903(3) 0.6893(3) 0.0809(13) Uani 1 1 d .
C5 C 0.6133(2) 0.0633(3) 0.7203(3) 0.0819(15) Uani 1 1 d .
H5 H 0.6449 0.0833 0.7508 0.098 Uiso 1 1 calc R
C6 C 0.5947(2) 0.0087(3) 0.7072(3) 0.0807(14) Uani 1 1 d .
H6 H 0.6113 -0.0083 0.7336 0.097 Uiso 1 1 calc R
C7 C 0.5358(3) -0.0804(3) 0.6326(4) 0.1010(19) Uani 1 1 d .
H7A H 0.5576 -0.0912 0.6637 0.152 Uiso 1 1 calc R
H7B H 0.5425 -0.0822 0.5762 0.152 Uiso 1 1 calc R
H7C H 0.4977 -0.1047 0.6440 0.152 Uiso 1 1 calc R
C8 C 0.6031(3) 0.1501(3) 0.7048(4) 0.0948(17) Uani 1 1 d .
H8 H 0.5938 0.1637 0.6563 0.114 Uiso 1 1 calc R
C9 C 0.5690(4) 0.1524(4) 0.7732(5) 0.134(3) Uani 1 1 d .
H9A H 0.5789 0.1898 0.7831 0.202 Uiso 1 1 calc R
H9B H 0.5754 0.1371 0.8209 0.202 Uiso 1 1 calc R
H9C H 0.5309 0.1317 0.7590 0.202 Uiso 1 1 calc R
C10 C 0.6636(3) 0.1872(4) 0.7200(5) 0.128(3) Uani 1 1 d .
H10A H 0.6711 0.2240 0.7289 0.192 Uiso 1 1 calc R
H10B H 0.6840 0.1865 0.6741 0.192 Uiso 1 1 calc R
H10C H 0.6743 0.1747 0.7668 0.192 Uiso 1 1 calc R
C11 C 0.6330(2) 0.1254(2) 0.5184(3) 0.0726(11) Uani 1 1 d U
C12 C 0.5971(3) 0.1411(3) 0.4850(3) 0.0898(15) Uani 1 1 d .
H12 H 0.5596 0.1190 0.4932 0.108 Uiso 1 1 calc R
C13 C 0.6161(3) 0.1888(3) 0.4401(4) 0.105(2) Uani 1 1 d .
H13 H 0.5914 0.1983 0.4195 0.125 Uiso 1 1 calc R
C14 C 0.6710(3) 0.2218(3) 0.4260(4) 0.1044(19) Uani 1 1 d .
H14 H 0.6834 0.2538 0.3962 0.125 Uiso 1 1 calc R
C15 C 0.7089(3) 0.2074(2) 0.4568(3) 0.0889(15) Uani 1 1 d .
H15 H 0.7463 0.2291 0.4470 0.107 Uiso 1 1 calc R
C16 C 0.6887(2) 0.1601(2) 0.5019(3) 0.0746(12) Uani 1 1 d .
C17 C 0.7223(2) 0.1391(2) 0.5355(3) 0.0702(11) Uani 1 1 d .
C18 C 0.7813(2) 0.1572(2) 0.5326(3) 0.0730(12) Uani 1 1 d .
C19 C 0.78672(18) 0.1170(2) 0.5814(3) 0.0683(10) Uani 1 1 d .
C20 C 0.8322(2) 0.1119(2) 0.6057(3) 0.0792(13) Uani 1 1 d .
H20 H 0.8676 0.1374 0.5899 0.095 Uiso 1 1 calc R
C21 C 0.8223(2) 0.0679(2) 0.6538(3) 0.0777(13) Uani 1 1 d .
C22 C 0.7691(2) 0.0292(2) 0.6768(3) 0.0739(11) Uani 1 1 d .
H22 H 0.7632 -0.0007 0.7080 0.089 Uiso 1 1 calc R
C23 C 0.72493(19) 0.0348(2) 0.6535(3) 0.0697(11) Uani 1 1 d .
H23 H 0.6896 0.0092 0.6693 0.084 Uiso 1 1 calc R
C24 C 0.73404(18) 0.07845(19) 0.6072(3) 0.0645(10) Uani 1 1 d .
C25 C 0.9059(3) 0.2525(3) 0.4477(5) 0.115(2) Uani 1 1 d .
H25A H 0.9416 0.2561 0.4503 0.172 Uiso 1 1 calc R
H25B H 0.9077 0.2851 0.4683 0.172 Uiso 1 1 calc R
H25C H 0.8937 0.2471 0.3926 0.172 Uiso 1 1 calc R
C26 C 0.8615(3) 0.0264(3) 0.7339(5) 0.1025(19) Uani 1 1 d .
H26A H 0.8967 0.0311 0.7475 0.154 Uiso 1 1 calc R
H26B H 0.8391 -0.0092 0.7106 0.154 Uiso 1 1 calc R
H26C H 0.8441 0.0297 0.7816 0.154 Uiso 1 1 calc R
O1W O 0.6667 0.3333 0.7082(13) 0.218(5) Uani 1 3 d S
O2W O 0.6589(8) 0.3002(6) 0.5613(13) 0.218(5) Uani 0.50 1 d P
O3W O 0.6667 0.3333 0.3333 0.218(5) Uani 1 6 d S
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'
Cl Cl 0.1484 0.1585 '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'
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
C11 Ru1 N1 76.47(18) . .
C11 Ru1 C5 121.7(2) . .
N1 Ru1 C5 94.75(17) . .
C11 Ru1 C4 93.1(2) . .
N1 Ru1 C4 113.98(18) . .
C5 Ru1 C4 38.1(2) . .
C11 Ru1 C3 94.1(2) . .
N1 Ru1 C3 151.5(2) . .
C5 Ru1 C3 67.09(19) . .
C4 Ru1 C3 38.7(2) . .
C11 Ru1 C2 117.9(2) . .
N1 Ru1 C2 165.60(18) . .
C5 Ru1 C2 78.4(2) . .
C4 Ru1 C2 68.0(2) . .
C3 Ru1 C2 35.7(2) . .
C11 Ru1 C6 157.3(2) . .
N1 Ru1 C6 102.64(16) . .
C5 Ru1 C6 35.7(2) . .
C4 Ru1 C6 66.3(2) . .
C3 Ru1 C6 75.83(19) . .
C2 Ru1 C6 64.46(19) . .
C11 Ru1 C1 154.1(2) . .
N1 Ru1 C1 129.28(17) . .
C5 Ru1 C1 65.1(2) . .
C4 Ru1 C1 79.2(2) . .
C3 Ru1 C1 64.5(2) . .
C2 Ru1 C1 36.33(19) . .
C6 Ru1 C1 35.3(2) . .
C11 Ru1 Cl1 86.88(14) . .
N1 Ru1 Cl1 87.50(10) . .
C5 Ru1 Cl1 151.08(17) . .
C4 Ru1 Cl1 157.92(15) . .
C3 Ru1 Cl1 119.23(15) . .
C2 Ru1 Cl1 92.55(16) . .
C6 Ru1 Cl1 115.80(16) . .
C1 Ru1 Cl1 91.31(15) . .
N2 O1 C25 110.2(5) . .
C21 O2 C26 117.7(5) . .
C17 N1 C24 109.8(4) . .
C17 N1 Ru1 118.2(3) . .
C24 N1 Ru1 132.0(3) . .
C18 N2 O1 110.3(5) . .
C6 C1 C2 118.0(6) . .
C6 C1 C7 119.9(5) . .
C2 C1 C7 122.1(5) . .
C6 C1 Ru1 72.2(3) . .
C2 C1 Ru1 68.0(3) . .
C7 C1 Ru1 127.9(4) . .
C3 C2 C1 120.9(5) . .
C3 C2 Ru1 71.2(3) . .
C1 C2 Ru1 75.7(3) . .
C3 C2 H2 119.5 . .
C1 C2 H2 119.5 . .
Ru1 C2 H2 125.3 . .
C2 C3 C4 122.9(5) . .
C2 C3 Ru1 73.1(3) . .
C4 C3 Ru1 70.4(3) . .
C2 C3 H3 118.5 . .
C4 C3 H3 118.5 . .
Ru1 C3 H3 130.9 . .
C5 C4 C3 114.2(5) . .
C5 C4 C8 125.4(5) . .
C3 C4 C8 120.4(5) . .
C5 C4 Ru1 70.7(3) . .
C3 C4 Ru1 70.9(3) . .
C8 C4 Ru1 127.1(4) . .
C6 C5 C4 122.6(5) . .
C6 C5 Ru1 77.4(3) . .
C4 C5 Ru1 71.2(3) . .
C6 C5 H5 118.7 . .
C4 C5 H5 118.7 . .
Ru1 C5 H5 124.1 . .
C5 C6 C1 120.8(5) . .
C5 C6 Ru1 66.9(3) . .
C1 C6 Ru1 72.5(3) . .
C5 C6 H6 119.6 . .
C1 C6 H6 119.6 . .
Ru1 C6 H6 134.5 . .
C1 C7 H7A 109.5 . .
C1 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C1 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C9 C8 C10 111.6(7) . .
C9 C8 C4 108.6(6) . .
C10 C8 C4 114.3(6) . .
C9 C8 H8 107.3 . .
C10 C8 H8 107.3 . .
C4 C8 H8 107.3 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C16 C11 C12 115.9(5) . .
C16 C11 Ru1 117.4(4) . .
C12 C11 Ru1 126.7(4) . .
C13 C12 C11 121.7(6) . .
C13 C12 H12 119.1 . .
C11 C12 H12 119.1 . .
C14 C13 C12 120.5(6) . .
C14 C13 H13 119.7 . .
C12 C13 H13 119.7 . .
C13 C14 C15 120.1(6) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C16 C15 C14 117.9(6) . .
C16 C15 H15 121.1 . .
C14 C15 H15 121.1 . .
C15 C16 C11 123.8(5) . .
C15 C16 C17 124.2(5) . .
C11 C16 C17 111.9(4) . .
N1 C17 C16 116.0(4) . .
N1 C17 C18 109.8(4) . .
C16 C17 C18 134.2(5) . .
N2 C18 C19 133.4(5) . .
N2 C18 C17 122.0(5) . .
C19 C18 C17 104.5(4) . .
C24 C19 C20 119.8(5) . .
C24 C19 C18 106.8(4) . .
C20 C19 C18 133.4(5) . .
C21 C20 C19 117.9(5) . .
C21 C20 H20 121.0 . .
C19 C20 H20 121.0 . .
O2 C21 C20 114.8(5) . .
O2 C21 C22 124.1(5) . .
C20 C21 C22 121.1(5) . .
C23 C22 C21 120.6(5) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
C24 C23 C22 119.1(5) . .
C24 C23 H23 120.4 . .
C22 C23 H23 120.4 . .
C23 C24 C19 121.5(4) . .
C23 C24 N1 129.6(4) . .
C19 C24 N1 109.0(4) . .
O1 C25 H25A 109.5 . .
O1 C25 H25B 109.5 . .
H25A C25 H25B 109.5 . .
O1 C25 H25C 109.5 . .
H25A C25 H25C 109.5 . .
H25B C25 H25C 109.5 . .
O2 C26 H26A 109.5 . .
O2 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
O2 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
O2W O2W O2W 60.000(8) 3_665 2_655
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ru1 C11 2.057(5) .
Ru1 N1 2.074(3) .
Ru1 C5 2.167(5) .
Ru1 C4 2.175(5) .
Ru1 C3 2.181(5) .
Ru1 C2 2.205(5) .
Ru1 C6 2.300(5) .
Ru1 C1 2.304(5) .
Ru1 Cl1 2.4058(11) .
O1 N2 1.390(6) .
O1 C25 1.464(7) .
O2 C21 1.368(6) .
O2 C26 1.410(8) .
N1 C17 1.313(6) .
N1 C24 1.423(6) .
N2 C18 1.283(6) .
C1 C6 1.396(8) .
C1 C2 1.409(8) .
C1 C7 1.532(9) .
C2 C3 1.343(8) .
C2 H2 0.9300 .
C3 C4 1.444(8) .
C3 H3 0.9300 .
C4 C5 1.417(8) .
C4 C8 1.529(9) .
C5 C6 1.373(8) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C9 1.509(9) .
C8 C10 1.512(10) .
C8 H8 0.9800 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C16 1.402(7) .
C11 C12 1.405(7) .
C12 C13 1.389(9) .
C12 H12 0.9300 .
C13 C14 1.371(10) .
C13 H13 0.9300 .
C14 C15 1.416(9) .
C14 H14 0.9300 .
C15 C16 1.381(7) .
C15 H15 0.9300 .
C16 C17 1.454(7) .
C17 C18 1.477(7) .
C18 C19 1.461(7) .
C19 C24 1.399(6) .
C19 C20 1.418(7) .
C20 C21 1.380(8) .
C20 H20 0.9300 .
C21 C22 1.398(7) .
C22 C23 1.387(7) .
C22 H22 0.9300 .
C23 C24 1.361(7) .
C23 H23 0.9300 .
C25 H25A 0.9600 .
C25 H25B 0.9600 .
C25 H25C 0.9600 .
C26 H26A 0.9600 .
C26 H26B 0.9600 .
C26 H26C 0.9600 .
O2W O2W 1.46(3) 3_665
O2W O2W 1.46(3) 2_655
