#------------------------------------------------------------------------------
#$Date: 2020-06-04 03:55:52 +0300 (Thu, 04 Jun 2020) $
#$Revision: 252591 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/76/4517650.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_4517650
loop_
_publ_author_name
'Matveevskaya, Vladislava V.'
'Pavlov, Dmitry I.'
'Sukhikh, Taisiya S.'
'Gushchin, Artem L.'
'Ivanov, Alexander Yu'
'Tennikova, Tatiana B.'
'Sharoyko, Vladimir V.'
'Baykov, Sergey V.'
'Benassi, Enrico'
'Potapov, Andrei S.'
_publ_section_title
;
 Arene-Ruthenium(II) Complexes Containing
 11H-Indeno[1,2-b]quinoxalin-11-one Derivatives and
 Tryptanthrin-6-oxime: Synthesis, Characterization, Cytotoxicity, and
 Catalytic Transfer Hydrogenation of Aryl Ketones.
;
_journal_issue                   19
_journal_name_full               'ACS omega'
_journal_page_first              11167
_journal_page_last               11179
_journal_paper_doi               10.1021/acsomega.0c01204
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C24 H21 Cl N4 O Ru, 0.5(C3 H7 N O)'
_chemical_formula_sum            'C25.5 H24.5 Cl N4.5 O1.5 Ru'
_chemical_formula_weight         554.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.453(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.414(2)
_cell_length_b                   16.071(2)
_cell_length_c                   7.6248(11)
_cell_measurement_reflns_used    9998
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.23
_cell_volume                     2237.4(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.730
_diffrn_reflns_theta_min         1.688
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0940 before and 0.0603 after correction. The Ratio of minimum to maximum transmission is 0.8505. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_description       plate
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.783
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5678
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0296
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0215P)²+1.3161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0597
_refine_ls_wR_factor_ref         0.0639
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4632
_reflns_number_total             5678
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c01204_si_005.cif
_cod_data_source_block           pot_rid_23_1
_cod_depositor_comments
'Adding full bibliography for 4517647--4517650.cif.'
_cod_original_formula_sum        'C25.50 H24.50 Cl N4.50 O1.50 Ru'
_cod_database_code               4517650
_shelx_shelxl_version_number     2017/1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N1S \\sim C2S \\sim C3S: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
3. Others
 Fixed Sof: O1S(0.5) N1S(0.5) C1S(0.5) H1S(0.5) C2S(0.5) H2SA(0.5) H2SB(0.5)
 H2SC(0.5) C3S(0.5) H3SA(0.5) H3SB(0.5) H3SC(0.5)
4.a Ternary CH refined with riding coordinates:
 C21(H21)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C19(H19), C20(H20), C1S(H1S)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C2S(H2SA,H2SB,
 H2SC), C3S(H3SA,H3SB,H3SC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.13558(2) 0.56269(2) 0.70101(2) 0.01157(5) Uani 1 1 d . . . . .
Cl1 Cl 0.12066(3) 0.61087(3) 0.40012(7) 0.01899(12) Uani 1 1 d . . . . .
O1 O 0.12729(8) 0.38871(10) 0.5545(2) 0.0229(4) Uani 1 1 d . . . . .
N1 N 0.16900(9) 0.44997(11) 0.5994(2) 0.0154(4) Uani 1 1 d . . . . .
N2 N 0.24819(9) 0.58796(11) 0.6912(2) 0.0156(4) Uani 1 1 d . . . . .
N3 N 0.40046(10) 0.57493(12) 0.6378(3) 0.0221(4) Uani 1 1 d . . . . .
N4 N 0.41787(11) 0.71109(14) 0.7328(3) 0.0320(5) Uani 1 1 d . . . . .
C1 C 0.24022(11) 0.44735(14) 0.5831(3) 0.0167(4) Uani 1 1 d . . . . .
C2 C 0.27836(11) 0.52118(14) 0.6309(3) 0.0168(4) Uani 1 1 d . . . . .
C3 C 0.35354(11) 0.51395(15) 0.6033(3) 0.0185(5) Uani 1 1 d . . . . .
C4 C 0.36138(12) 0.42908(14) 0.5343(3) 0.0199(5) Uani 1 1 d . . . . .
C5 C 0.42167(13) 0.38842(16) 0.4813(3) 0.0259(5) Uani 1 1 d . . . . .
H5 H 0.466887 0.414791 0.487588 0.031 Uiso 1 1 calc R . . . .
C6 C 0.41252(13) 0.30771(17) 0.4189(3) 0.0307(6) Uani 1 1 d . . . . .
H6 H 0.452168 0.279809 0.382312 0.037 Uiso 1 1 calc R . . . .
C7 C 0.34532(13) 0.26751(16) 0.4098(3) 0.0273(5) Uani 1 1 d . . . . .
H7 H 0.341028 0.212991 0.368863 0.033 Uiso 1 1 calc R . . . .
C8 C 0.28440(13) 0.30733(15) 0.4609(3) 0.0219(5) Uani 1 1 d . . . . .
H8 H 0.239468 0.280260 0.453510 0.026 Uiso 1 1 calc R . . . .
C9 C 0.29220(11) 0.38860(14) 0.5231(3) 0.0175(5) Uani 1 1 d . . . . .
C10 C 0.29484(12) 0.65513(14) 0.7210(3) 0.0186(5) Uani 1 1 d . . . . .
C11 C 0.37058(12) 0.64650(15) 0.6984(3) 0.0215(5) Uani 1 1 d . . . . .
C12 C 0.39180(15) 0.78285(17) 0.7802(4) 0.0351(7) Uani 1 1 d . . . . .
H12 H 0.424633 0.826503 0.805725 0.042 Uiso 1 1 calc R . . . .
C13 C 0.31790(13) 0.79764(16) 0.7946(3) 0.0284(6) Uani 1 1 d . . . . .
H13 H 0.302097 0.850405 0.822519 0.034 Uiso 1 1 calc R . . . .
C14 C 0.26929(13) 0.73305(14) 0.7669(3) 0.0217(5) Uani 1 1 d . . . . .
H14 H 0.220093 0.740872 0.778473 0.026 Uiso 1 1 calc R . . . .
C15 C 0.11835(11) 0.51042(14) 0.9608(3) 0.0158(4) Uani 1 1 d . . . . .
C16 C 0.05630(11) 0.49427(14) 0.8320(3) 0.0166(5) Uani 1 1 d . . . . .
H16 H 0.040086 0.439727 0.814605 0.020 Uiso 1 1 calc R . . . .
C17 C 0.01903(11) 0.55777(14) 0.7310(3) 0.0170(4) Uani 1 1 d . . . . .
H17 H -0.019943 0.544647 0.645318 0.020 Uiso 1 1 calc R . . . .
C18 C 0.04089(11) 0.64299(14) 0.7597(3) 0.0159(4) Uani 1 1 d . . . . .
C19 C 0.10155(11) 0.66026(14) 0.8854(3) 0.0168(4) Uani 1 1 d . . . . .
H19 H 0.116115 0.715078 0.907607 0.020 Uiso 1 1 calc R . . . .
C20 C 0.14097(12) 0.59430(14) 0.9792(3) 0.0173(5) Uani 1 1 d . . . . .
H20 H 0.183145 0.606911 1.055441 0.021 Uiso 1 1 calc R . . . .
C21 C 0.16000(12) 0.44288(15) 1.0734(3) 0.0212(5) Uani 1 1 d . . . . .
H21 H 0.151299 0.452653 1.195810 0.025 Uiso 1 1 calc R . . . .
C22 C 0.13238(14) 0.35558(15) 1.0247(4) 0.0284(6) Uani 1 1 d . . . . .
H22A H 0.080435 0.353254 1.027295 0.043 Uiso 1 1 calc GR . . . .
H22B H 0.156284 0.316392 1.108020 0.043 Uiso 1 1 calc GR . . . .
H22C H 0.142989 0.342039 0.908058 0.043 Uiso 1 1 calc GR . . . .
C23 C 0.24279(13) 0.44801(17) 1.0710(4) 0.0317(6) Uani 1 1 d . . . . .
H23A H 0.253634 0.439588 0.952441 0.047 Uiso 1 1 calc GR . . . .
H23B H 0.266633 0.405831 1.146884 0.047 Uiso 1 1 calc GR . . . .
H23C H 0.260061 0.501836 1.112001 0.047 Uiso 1 1 calc GR . . . .
C24 C 0.00178(12) 0.71131(14) 0.6528(3) 0.0214(5) Uani 1 1 d . . . . .
H24A H 0.029468 0.761890 0.671085 0.032 Uiso 1 1 calc GR . . . .
H24B H -0.045771 0.719211 0.688962 0.032 Uiso 1 1 calc GR . . . .
H24C H -0.003463 0.696702 0.529714 0.032 Uiso 1 1 calc GR . . . .
O1S O 0.4055(3) 0.9560(4) 0.6464(11) 0.097(2) Uani 0.5 1 d . . P A -1
N1S N 0.5078(18) 0.997(3) 0.511(6) 0.029(3) Uani 0.5 1 d . U P A -1
C1S C 0.4384(4) 1.0087(5) 0.5775(11) 0.0563(19) Uani 0.5 1 d . . P A -1
H1S H 0.417476 1.061379 0.566113 0.068 Uiso 0.5 1 calc R . P A -1
C2S C 0.5366(4) 1.0567(4) 0.4185(10) 0.0551(18) Uani 0.5 1 d . U P A -1
H2SA H 0.587648 1.062904 0.461225 0.083 Uiso 0.5 1 calc GR . P A -1
H2SB H 0.511718 1.108375 0.432404 0.083 Uiso 0.5 1 calc GR . P A -1
H2SC H 0.530951 1.041643 0.295713 0.083 Uiso 0.5 1 calc GR . P A -1
C3S C 0.5354(3) 0.9122(3) 0.5103(8) 0.0393(14) Uani 0.5 1 d . U P A -1
H3SA H 0.503443 0.879351 0.428100 0.059 Uiso 0.5 1 calc GR . P A -1
H3SB H 0.537111 0.888889 0.626710 0.059 Uiso 0.5 1 calc GR . P A -1
H3SC H 0.583684 0.912358 0.475812 0.059 Uiso 0.5 1 calc GR . P A -1
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
_geom_angle_publ_flag
N1 Ru1 Cl1 85.87(5) . . ?
N1 Ru1 N2 79.47(7) . . ?
N1 Ru1 C15 94.94(8) . . ?
N1 Ru1 C16 88.83(7) . . ?
N1 Ru1 C17 110.28(8) . . ?
N1 Ru1 C18 146.99(7) . . ?
N1 Ru1 C19 162.52(8) . . ?
N1 Ru1 C20 125.85(8) . . ?
N2 Ru1 Cl1 84.04(5) . . ?
N2 Ru1 C15 110.99(7) . . ?
N2 Ru1 C16 146.16(8) . . ?
N2 Ru1 C17 170.24(8) . . ?
N2 Ru1 C18 132.81(7) . . ?
N2 Ru1 C19 103.95(7) . . ?
N2 Ru1 C20 93.93(8) . . ?
C15 Ru1 Cl1 164.87(6) . . ?
C15 Ru1 C18 80.55(8) . . ?
C15 Ru1 C19 67.73(8) . . ?
C16 Ru1 Cl1 127.00(6) . . ?
C16 Ru1 C15 38.07(8) . . ?
C16 Ru1 C17 37.53(8) . . ?
C16 Ru1 C18 67.43(8) . . ?
C16 Ru1 C19 78.87(8) . . ?
C17 Ru1 Cl1 96.85(6) . . ?
C17 Ru1 C15 68.67(8) . . ?
C17 Ru1 C18 37.62(8) . . ?
C17 Ru1 C19 66.63(8) . . ?
C18 Ru1 Cl1 90.53(6) . . ?
C19 Ru1 Cl1 111.44(6) . . ?
C19 Ru1 C18 36.23(8) . . ?
C20 Ru1 Cl1 147.41(6) . . ?
C20 Ru1 C15 37.59(8) . . ?
C20 Ru1 C16 67.50(8) . . ?
C20 Ru1 C17 80.06(8) . . ?
C20 Ru1 C18 67.15(8) . . ?
C20 Ru1 C19 37.54(8) . . ?
O1 N1 Ru1 125.07(13) . . ?
O1 N1 C1 121.26(18) . . ?
C1 N1 Ru1 113.66(14) . . ?
C2 N2 Ru1 108.31(14) . . ?
C2 N2 C10 114.37(18) . . ?
C10 N2 Ru1 137.20(15) . . ?
C3 N3 C11 114.17(18) . . ?
C12 N4 C11 118.3(2) . . ?
N1 C1 C2 114.48(19) . . ?
N1 C1 C9 137.9(2) . . ?
C2 C1 C9 107.58(18) . . ?
N2 C2 C1 124.04(19) . . ?
N2 C2 C3 125.2(2) . . ?
C1 C2 C3 110.7(2) . . ?
N3 C3 C2 122.3(2) . . ?
N3 C3 C4 132.1(2) . . ?
C2 C3 C4 105.59(19) . . ?
C5 C4 C3 131.0(2) . . ?
C5 C4 C9 120.6(2) . . ?
C9 C4 C3 108.40(19) . . ?
C6 C5 C4 118.3(2) . . ?
C5 C6 C7 121.4(2) . . ?
C6 C7 C8 121.2(2) . . ?
C7 C8 C9 118.5(2) . . ?
C4 C9 C1 107.69(19) . . ?
C8 C9 C1 132.2(2) . . ?
C8 C9 C4 120.1(2) . . ?
N2 C10 C11 119.9(2) . . ?
N2 C10 C14 121.3(2) . . ?
C14 C10 C11 118.7(2) . . ?
N3 C11 C10 123.8(2) . . ?
N4 C11 N3 115.3(2) . . ?
N4 C11 C10 120.8(2) . . ?
N4 C12 C13 124.2(2) . . ?
C14 C13 C12 118.8(2) . . ?
C13 C14 C10 118.9(2) . . ?
C16 C15 Ru1 69.44(12) . . ?
C16 C15 C21 123.72(19) . . ?
C20 C15 Ru1 69.63(12) . . ?
C20 C15 C16 116.13(19) . . ?
C20 C15 C21 120.15(19) . . ?
C21 C15 Ru1 130.80(15) . . ?
C15 C16 Ru1 72.49(12) . . ?
C17 C16 Ru1 71.91(12) . . ?
C17 C16 C15 122.4(2) . . ?
C16 C17 Ru1 70.56(12) . . ?
C16 C17 C18 120.2(2) . . ?
C18 C17 Ru1 73.87(11) . . ?
C17 C18 Ru1 68.51(11) . . ?
C17 C18 C24 120.8(2) . . ?
C19 C18 Ru1 71.44(12) . . ?
C19 C18 C17 118.4(2) . . ?
C19 C18 C24 120.8(2) . . ?
C24 C18 Ru1 129.86(15) . . ?
C18 C19 Ru1 72.33(12) . . ?
C18 C19 C20 120.3(2) . . ?
C20 C19 Ru1 68.27(12) . . ?
C15 C20 Ru1 72.78(13) . . ?
C15 C20 C19 122.4(2) . . ?
C19 C20 Ru1 74.19(13) . . ?
C15 C21 C23 112.55(19) . . ?
C22 C21 C15 112.98(19) . . ?
C22 C21 C23 110.4(2) . . ?
C1S N1S C3S 116(4) . . ?
C2S N1S C1S 122(3) . . ?
C2S N1S C3S 120(4) . . ?
O1S C1S N1S 126(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 Cl1 2.4031(6) . ?
Ru1 N1 2.0940(18) . ?
Ru1 N2 2.1237(17) . ?
Ru1 C15 2.212(2) . ?
Ru1 C16 2.172(2) . ?
Ru1 C17 2.189(2) . ?
Ru1 C18 2.260(2) . ?
Ru1 C19 2.249(2) . ?
Ru1 C20 2.171(2) . ?
O1 N1 1.268(2) . ?
N1 C1 1.334(3) . ?
N2 C2 1.318(3) . ?
N2 C10 1.380(3) . ?
N3 C3 1.310(3) . ?
N3 C11 1.380(3) . ?
N4 C11 1.358(3) . ?
N4 C12 1.318(3) . ?
C1 C2 1.403(3) . ?
C1 C9 1.460(3) . ?
C2 C3 1.432(3) . ?
C3 C4 1.475(3) . ?
C4 C5 1.393(3) . ?
C4 C9 1.423(3) . ?
C5 C6 1.384(4) . ?
C6 C7 1.390(4) . ?
C7 C8 1.390(3) . ?
C8 C9 1.391(3) . ?
C10 C11 1.434(3) . ?
C10 C14 1.398(3) . ?
C12 C13 1.400(4) . ?
C13 C14 1.369(3) . ?
C15 C16 1.430(3) . ?
C15 C20 1.413(3) . ?
C15 C21 1.527(3) . ?
C16 C17 1.403(3) . ?
C17 C18 1.436(3) . ?
C18 C19 1.402(3) . ?
C18 C24 1.495(3) . ?
C19 C20 1.424(3) . ?
C21 C22 1.522(3) . ?
C21 C23 1.529(3) . ?
O1S C1S 1.202(8) . ?
N1S C1S 1.45(5) . ?
N1S C2S 1.34(6) . ?
N1S C3S 1.46(5) . ?
