#------------------------------------------------------------------------------ #$Date: 2021-05-14 06:25:59 +0300 (Fri, 14 May 2021) $ #$Revision: 265209 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060681.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_7060681 loop_ _publ_author_name '\,Cicek, Metin' 'G\"urb\"uz, Nevin' '\"Ozdemir, Nam\?ik' '\"Ozdemir, \.Ismail' 'Ispir, Esin' _publ_section_title ; Half-sandwich Ru(II) arene complexes that bearing benzimidazole ligands for the N‐alkylation reaction of aniline with alcohols under solvent-free medium ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ01539G _journal_year 2021 _chemical_formula_moiety 'C21 H28 Cl2 N2 O2 Ru' _chemical_formula_sum 'C21 H28 Cl2 N2 O2 Ru' _chemical_formula_weight 512.42 _space_group_crystal_system trigonal _space_group_IT_number 148 _space_group_name_Hall '-R 3' _space_group_name_H-M_alt 'R -3 :H' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-02-05 deposited with the CCDC. 2021-05-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 18 _cell_length_a 30.0916(15) _cell_length_b 30.0916(15) _cell_length_c 13.6690(7) _cell_measurement_reflns_used 19048 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.17 _cell_measurement_theta_min 1.68 _cell_volume 10719.1(9) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material 'OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation '0.8 mm diameter, multiple pinhole' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_unetI/netI 0.0598 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 17929 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.726 _diffrn_reflns_theta_min 1.682 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _exptl_absorpt_coefficient_mu 0.900 _exptl_absorpt_correction_T_max 0.9115 _exptl_absorpt_correction_T_min 0.7227 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.429 _exptl_crystal_description prism _exptl_crystal_F_000 4716 _exptl_crystal_size_max 0.600 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.130 _refine_diff_density_max 0.417 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.926 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 258 _refine_ls_number_reflns 5579 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.926 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0385 _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/[\s^2^(Fo^2^)+(0.0320P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.0752 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3652 _reflns_number_total 5579 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01539g2.cif _cod_data_source_block namiko217 _cod_original_cell_volume 10719.1(12) _cod_database_code 7060681 _shelx_shelxl_version_number 2018/3 _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 0.614 _shelx_estimated_absorpt_t_max 0.892 _shelx_res_file ; TITL namiko217 shelx.res created by SHELXL-2018/3 at 19:50:25 on 05-Feb-2021 CELL 0.71073 30.0916 30.0916 13.6690 90.000 90.000 120.000 ZERR 18.00 0.0015 0.0015 0.0007 0.000 0.000 0.000 LATT 3 SYMM - Y, X - Y, Z SYMM - X + Y, - X, Z SFAC C H CL N O RU UNIT 378 504 36 36 36 18 MERG 2 FMAP 2 PLAN 3 SIZE 0.130 0.130 0.600 ACTA BOND $H CONF L.S. 20 TEMP 23.00 WGHT 0.032000 FVAR 0.12278 RU1 6 0.857267 0.635986 0.341452 11.00000 0.04264 0.05615 = 0.03273 0.00186 0.00011 0.02969 CL1 3 0.765642 0.602193 0.351538 11.00000 0.04423 0.08075 = 0.05093 0.00621 0.00089 0.03356 CL2 3 0.867809 0.720282 0.367393 11.00000 0.08204 0.06219 = 0.04397 0.00337 0.00212 0.04353 O1 5 0.769453 0.483921 0.800160 11.00000 0.08658 0.10243 = 0.09167 0.04297 0.01375 0.04133 O2 5 0.785467 0.491547 0.636136 11.00000 0.21266 0.08745 = 0.07877 0.00307 0.00728 0.08984 N1 4 0.855370 0.631295 0.497427 11.00000 0.05149 0.05331 = 0.03474 0.00193 0.00036 0.03022 N2 4 0.825408 0.599134 0.645785 11.00000 0.06140 0.06003 = 0.03658 0.00536 0.00467 0.03831 C1 1 0.816911 0.595642 0.548777 11.00000 0.05665 0.06098 = 0.03930 0.00287 -0.00039 0.03572 AFIX 43 H1 2 0.786656 0.570377 0.520423 11.00000 -1.20000 AFIX 0 C2 1 0.892923 0.661086 0.567307 11.00000 0.05875 0.05514 = 0.03834 -0.00127 -0.00360 0.03715 C3 1 0.941799 0.702857 0.556963 11.00000 0.06026 0.06082 = 0.05549 0.00013 -0.00614 0.02878 AFIX 43 H3 2 0.954838 0.716792 0.495770 11.00000 -1.20000 AFIX 0 C4 1 0.970663 0.723202 0.641394 11.00000 0.06704 0.07107 = 0.07494 -0.01254 -0.01420 0.03149 AFIX 43 H4 2 1.003919 0.750814 0.636459 11.00000 -1.20000 AFIX 0 C5 1 0.950684 0.702962 0.733853 11.00000 0.09330 0.08308 = 0.05506 -0.01687 -0.02375 0.05116 AFIX 43 H5 2 0.970968 0.717851 0.788847 11.00000 -1.20000 AFIX 0 C6 1 0.902602 0.662260 0.745735 11.00000 0.08397 0.07513 = 0.04025 -0.00512 -0.00753 0.05014 AFIX 43 H6 2 0.889406 0.649296 0.807376 11.00000 -1.20000 AFIX 0 C7 1 0.873898 0.640801 0.660389 11.00000 0.06041 0.05746 = 0.03923 -0.00250 -0.00295 0.04022 C8 1 0.791721 0.562055 0.718753 11.00000 0.07258 0.07656 = 0.04424 0.01476 0.01630 0.04488 AFIX 23 H8A 2 0.756254 0.550268 0.701655 11.00000 -1.20000 H8B 2 0.798339 0.578661 0.782155 11.00000 -1.20000 AFIX 0 C9 1 0.799969 0.516309 0.725149 11.00000 0.08513 0.07030 = 0.06532 0.02294 0.01546 0.04044 AFIX 13 H9 2 0.836203 0.527907 0.737889 11.00000 -1.20000 AFIX 0 C10 1 0.796680 0.486787 0.886822 11.00000 0.17746 0.17198 = 0.08039 0.03116 -0.00205 0.11784 AFIX 137 H10A 2 0.828641 0.488867 0.869997 11.00000 -1.50000 H10B 2 0.776560 0.456707 0.925792 11.00000 -1.50000 H10C 2 0.803268 0.516728 0.923341 11.00000 -1.50000 AFIX 0 C11 1 0.796275 0.449808 0.626530 11.00000 0.33120 0.09980 = 0.14864 0.01190 0.04490 0.13256 AFIX 137 H11A 2 0.827842 0.458748 0.659449 11.00000 -1.50000 H11B 2 0.799289 0.443807 0.558513 11.00000 -1.50000 H11C 2 0.768838 0.419277 0.655278 11.00000 -1.50000 AFIX 0 C12 1 0.971280 0.725836 0.256865 11.00000 0.06012 0.09939 = 0.08907 0.02094 0.02368 0.02656 AFIX 137 H12A 2 0.987826 0.734969 0.319585 11.00000 -1.50000 H12B 2 0.956743 0.747165 0.242689 11.00000 -1.50000 H12C 2 0.995988 0.730693 0.207457 11.00000 -1.50000 AFIX 0 C13 1 0.929602 0.670738 0.258212 11.00000 0.04552 0.07928 = 0.04975 0.00831 0.01284 0.03384 C14 1 0.928899 0.635392 0.326156 11.00000 0.04569 0.08721 = 0.04920 -0.00637 -0.00190 0.04189 AFIX 43 H14 2 0.956076 0.645800 0.369694 11.00000 -1.20000 AFIX 0 C15 1 0.887571 0.584166 0.329650 11.00000 0.06297 0.07619 = 0.04396 -0.00202 -0.00327 0.05132 AFIX 43 H15 2 0.887954 0.561640 0.375772 11.00000 -1.20000 AFIX 0 C16 1 0.845974 0.566823 0.264510 11.00000 0.06009 0.06630 = 0.04887 -0.01104 -0.00607 0.04119 C17 1 0.847194 0.602538 0.195731 11.00000 0.06257 0.08334 = 0.03729 -0.01073 -0.00899 0.04920 AFIX 43 H17 2 0.820159 0.591924 0.151781 11.00000 -1.20000 AFIX 0 C18 1 0.887358 0.652912 0.191531 11.00000 0.06677 0.08925 = 0.03832 0.00863 0.00884 0.05189 AFIX 43 H18 2 0.886822 0.675228 0.145096 11.00000 -1.20000 AFIX 0 C19 1 0.801036 0.512355 0.263821 11.00000 0.07229 0.07322 = 0.08115 -0.01693 -0.01223 0.04172 AFIX 13 H19 2 0.770029 0.514399 0.251439 11.00000 -1.20000 AFIX 0 C20 1 0.792838 0.483674 0.358976 11.00000 0.10249 0.07299 = 0.11918 0.00071 0.01459 0.03831 AFIX 137 H20A 2 0.821715 0.479134 0.371463 11.00000 -1.50000 H20B 2 0.762240 0.450726 0.354504 11.00000 -1.50000 H20C 2 0.789352 0.502945 0.411399 11.00000 -1.50000 AFIX 0 C21 1 0.807598 0.483777 0.177265 11.00000 0.12891 0.09685 = 0.11387 -0.05145 -0.02480 0.05572 AFIX 137 H21A 2 0.808566 0.500951 0.117439 11.00000 -1.50000 H21B 2 0.779282 0.449228 0.175514 11.00000 -1.50000 H21C 2 0.839058 0.483249 0.184615 11.00000 -1.50000 AFIX 0 HKLF 4 REM namiko217 REM wR2 = 0.0752, GooF = S = 0.926, Restrained GooF = 0.926 for all data REM R1 = 0.0385 for 3652 Fo > 4sig(Fo) and 0.0769 for all 5579 data REM 258 parameters refined using 0 restraints END WGHT 0.0320 0.0000 REM Highest difference peak 0.417, deepest hole -0.374, 1-sigma level 0.068 Q1 1 0.6667 0.3333 0.7397 10.33333 0.05 0.42 Q2 1 0.8446 0.6585 0.2797 11.00000 0.05 0.42 Q3 1 0.8640 0.6155 0.4176 11.00000 0.05 0.41 ; _shelx_res_checksum 31051 loop_ _space_group_symop_operation_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_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 0.85727(2) 0.63599(2) 0.34145(2) 0.04162(8) Uani 1 1 d . . . . . Cl1 Cl 0.76564(3) 0.60219(4) 0.35154(7) 0.0576(2) Uani 1 1 d . . . . . Cl2 Cl 0.86781(4) 0.72028(3) 0.36739(6) 0.0594(2) Uani 1 1 d . . . . . O1 O 0.76945(12) 0.48392(12) 0.8002(3) 0.0962(10) Uani 1 1 d . . . . . O2 O 0.78547(17) 0.49155(13) 0.6361(3) 0.1197(13) Uani 1 1 d . . . . . N1 N 0.85537(10) 0.63129(9) 0.49743(17) 0.0447(5) Uani 1 1 d . . . . . N2 N 0.82541(10) 0.59913(10) 0.64579(19) 0.0491(6) Uani 1 1 d . . . . . C1 C 0.81691(12) 0.59564(13) 0.5488(2) 0.0495(7) Uani 1 1 d . . . . . H1 H 0.786656 0.570377 0.520423 0.059 Uiso 1 1 calc R U . . . C2 C 0.89292(12) 0.66109(12) 0.5673(2) 0.0469(7) Uani 1 1 d . . . . . C3 C 0.94180(13) 0.70286(13) 0.5570(3) 0.0595(9) Uani 1 1 d . . . . . H3 H 0.954838 0.716792 0.495770 0.071 Uiso 1 1 calc R U . . . C4 C 0.97066(16) 0.72320(15) 0.6414(3) 0.0724(11) Uani 1 1 d . . . . . H4 H 1.003919 0.750814 0.636459 0.087 Uiso 1 1 calc R U . . . C5 C 0.95068(17) 0.70296(16) 0.7339(3) 0.0740(11) Uani 1 1 d . . . . . H5 H 0.970968 0.717851 0.788847 0.089 Uiso 1 1 calc R U . . . C6 C 0.90260(15) 0.66226(14) 0.7457(3) 0.0618(9) Uani 1 1 d . . . . . H6 H 0.889406 0.649296 0.807376 0.074 Uiso 1 1 calc R U . . . C7 C 0.87390(12) 0.64080(12) 0.6604(2) 0.0476(7) Uani 1 1 d . . . . . C8 C 0.79172(14) 0.56206(14) 0.7188(3) 0.0611(9) Uani 1 1 d . . . . . H8A H 0.756254 0.550268 0.701655 0.073 Uiso 1 1 calc R U . . . H8B H 0.798339 0.578661 0.782155 0.073 Uiso 1 1 calc R U . . . C9 C 0.79997(17) 0.51631(15) 0.7251(3) 0.0729(11) Uani 1 1 d . . . . . H9 H 0.836203 0.527907 0.737889 0.087 Uiso 1 1 calc R U . . . C10 C 0.7967(3) 0.4868(3) 0.8868(4) 0.130(2) Uani 1 1 d . . . . . H10A H 0.828641 0.488867 0.869997 0.195 Uiso 1 1 calc R U . . . H10B H 0.776560 0.456707 0.925792 0.195 Uiso 1 1 calc R U . . . H10C H 0.803268 0.516728 0.923341 0.195 Uiso 1 1 calc R U . . . C11 C 0.7963(4) 0.4498(2) 0.6265(6) 0.182(4) Uani 1 1 d . . . . . H11A H 0.827842 0.458748 0.659449 0.273 Uiso 1 1 calc R U . . . H11B H 0.799289 0.443807 0.558513 0.273 Uiso 1 1 calc R U . . . H11C H 0.768838 0.419277 0.655278 0.273 Uiso 1 1 calc R U . . . C12 C 0.97128(15) 0.72584(17) 0.2569(4) 0.0888(14) Uani 1 1 d . . . . . H12A H 0.987826 0.734969 0.319585 0.133 Uiso 1 1 calc R U . . . H12B H 0.956743 0.747165 0.242689 0.133 Uiso 1 1 calc R U . . . H12C H 0.995988 0.730693 0.207457 0.133 Uiso 1 1 calc R U . . . C13 C 0.92960(12) 0.67074(14) 0.2582(3) 0.0570(9) Uani 1 1 d . . . . . C14 C 0.92890(12) 0.63539(14) 0.3262(3) 0.0569(9) Uani 1 1 d . . . . . H14 H 0.956076 0.645800 0.369694 0.068 Uiso 1 1 calc R U . . . C15 C 0.88757(13) 0.58417(14) 0.3296(2) 0.0537(8) Uani 1 1 d . . . . . H15 H 0.887954 0.561640 0.375772 0.064 Uiso 1 1 calc R U . . . C16 C 0.84597(13) 0.56682(13) 0.2645(3) 0.0542(8) Uani 1 1 d . . . . . C17 C 0.84719(13) 0.60254(14) 0.1957(2) 0.0554(8) Uani 1 1 d . . . . . H17 H 0.820159 0.591924 0.151781 0.066 Uiso 1 1 calc R U . . . C18 C 0.88736(14) 0.65291(15) 0.1915(2) 0.0591(9) Uani 1 1 d . . . . . H18 H 0.886822 0.675228 0.145096 0.071 Uiso 1 1 calc R U . . . C19 C 0.80104(16) 0.51235(15) 0.2638(3) 0.0732(11) Uani 1 1 d . . . . . H19 H 0.770029 0.514399 0.251439 0.088 Uiso 1 1 calc R U . . . C20 C 0.79284(19) 0.48367(18) 0.3590(4) 0.1007(16) Uani 1 1 d . . . . . H20A H 0.821715 0.479134 0.371463 0.151 Uiso 1 1 calc R U . . . H20B H 0.762240 0.450726 0.354504 0.151 Uiso 1 1 calc R U . . . H20C H 0.789352 0.502945 0.411399 0.151 Uiso 1 1 calc R U . . . C21 C 0.8076(2) 0.4838(2) 0.1773(4) 0.1135(18) Uani 1 1 d . . . . . H21A H 0.808566 0.500951 0.117439 0.170 Uiso 1 1 calc R U . . . H21B H 0.779282 0.449228 0.175514 0.170 Uiso 1 1 calc R U . . . H21C H 0.839058 0.483249 0.184615 0.170 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Ru1 0.04264(14) 0.05615(16) 0.03273(12) 0.00186(11) 0.00011(11) 0.02969(12) Cl1 0.0442(4) 0.0808(6) 0.0509(5) 0.0062(4) 0.0009(4) 0.0336(4) Cl2 0.0820(6) 0.0622(5) 0.0440(5) 0.0034(4) 0.0021(4) 0.0435(5) O1 0.087(2) 0.102(2) 0.092(2) 0.0430(19) 0.0138(18) 0.0413(18) O2 0.213(4) 0.087(2) 0.079(2) 0.0031(19) 0.007(3) 0.090(3) N1 0.0515(14) 0.0533(15) 0.0347(13) 0.0019(12) 0.0004(12) 0.0302(13) N2 0.0614(16) 0.0600(16) 0.0366(15) 0.0054(13) 0.0047(12) 0.0383(14) C1 0.0567(18) 0.0610(19) 0.0393(18) 0.0029(15) -0.0004(15) 0.0357(16) C2 0.0587(19) 0.0551(18) 0.0383(17) -0.0013(14) -0.0036(15) 0.0372(16) C3 0.060(2) 0.061(2) 0.055(2) 0.0001(17) -0.0061(17) 0.0288(18) C4 0.067(2) 0.071(2) 0.075(3) -0.013(2) -0.014(2) 0.031(2) C5 0.093(3) 0.083(3) 0.055(3) -0.017(2) -0.024(2) 0.051(3) C6 0.084(3) 0.075(2) 0.0402(19) -0.0051(17) -0.0075(18) 0.050(2) C7 0.0604(19) 0.0575(18) 0.0392(17) -0.0025(15) -0.0030(14) 0.0402(17) C8 0.073(2) 0.077(2) 0.044(2) 0.0148(18) 0.0163(18) 0.045(2) C9 0.085(3) 0.070(2) 0.065(3) 0.023(2) 0.015(2) 0.040(2) C10 0.177(6) 0.172(6) 0.080(4) 0.031(4) -0.002(4) 0.118(5) C11 0.331(12) 0.100(4) 0.149(7) 0.012(4) 0.045(7) 0.133(6) C12 0.060(2) 0.099(3) 0.089(3) 0.021(3) 0.024(2) 0.027(2) C13 0.0455(18) 0.079(2) 0.050(2) 0.0083(18) 0.0128(15) 0.0338(17) C14 0.0457(18) 0.087(3) 0.049(2) -0.0064(19) -0.0019(15) 0.0419(19) C15 0.063(2) 0.076(2) 0.0440(19) -0.0020(17) -0.0033(16) 0.0513(19) C16 0.0601(19) 0.066(2) 0.049(2) -0.0110(17) -0.0061(16) 0.0412(18) C17 0.063(2) 0.083(2) 0.0373(18) -0.0107(17) -0.0090(15) 0.049(2) C18 0.067(2) 0.089(3) 0.0383(19) 0.0086(18) 0.0088(17) 0.052(2) C19 0.072(2) 0.073(2) 0.081(3) -0.017(2) -0.012(2) 0.042(2) C20 0.102(4) 0.073(3) 0.119(5) 0.001(3) 0.015(3) 0.038(3) C21 0.129(4) 0.097(4) 0.114(5) -0.051(3) -0.025(4) 0.056(3) 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 C15 91.93(11) . . ? N1 Ru1 C14 95.12(12) . . ? C15 Ru1 C14 38.07(13) . . ? N1 Ru1 C17 152.54(12) . . ? C15 Ru1 C17 67.19(12) . . ? C14 Ru1 C17 79.53(13) . . ? N1 Ru1 C18 160.34(12) . . ? C15 Ru1 C18 79.89(13) . . ? C14 Ru1 C18 67.45(13) . . ? C17 Ru1 C18 37.00(13) . . ? N1 Ru1 C16 115.35(12) . . ? C15 Ru1 C16 37.53(12) . . ? C14 Ru1 C16 68.37(13) . . ? C17 Ru1 C16 37.64(13) . . ? C18 Ru1 C16 67.92(14) . . ? N1 Ru1 C13 122.32(12) . . ? C15 Ru1 C13 68.42(13) . . ? C14 Ru1 C13 37.42(13) . . ? C17 Ru1 C13 67.91(13) . . ? C18 Ru1 C13 38.03(13) . . ? C16 Ru1 C13 81.42(13) . . ? N1 Ru1 Cl1 85.88(7) . . ? C15 Ru1 Cl1 120.15(10) . . ? C14 Ru1 Cl1 158.15(10) . . ? C17 Ru1 Cl1 89.53(9) . . ? C18 Ru1 Cl1 113.71(10) . . ? C16 Ru1 Cl1 91.44(9) . . ? C13 Ru1 Cl1 151.32(10) . . ? N1 Ru1 Cl2 84.73(7) . . ? C15 Ru1 Cl2 151.88(10) . . ? C14 Ru1 Cl2 114.31(10) . . ? C17 Ru1 Cl2 122.15(10) . . ? C18 Ru1 Cl2 94.07(10) . . ? C16 Ru1 Cl2 159.78(10) . . ? C13 Ru1 Cl2 89.86(10) . . ? Cl1 Ru1 Cl2 87.52(3) . . ? C9 O1 C10 114.4(4) . . ? C9 O2 C11 113.6(4) . . ? C1 N1 C2 104.8(3) . . ? C1 N1 Ru1 124.6(2) . . ? C2 N1 Ru1 130.5(2) . . ? C1 N2 C7 106.6(3) . . ? C1 N2 C8 125.5(3) . . ? C7 N2 C8 127.5(3) . . ? N1 C1 N2 113.9(3) . . ? N1 C1 H1 123.0 . . ? N2 C1 H1 123.0 . . ? C3 C2 C7 120.3(3) . . ? C3 C2 N1 131.3(3) . . ? C7 C2 N1 108.4(3) . . ? C2 C3 C4 117.5(4) . . ? C2 C3 H3 121.2 . . ? C4 C3 H3 121.2 . . ? C3 C4 C5 121.3(4) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 122.1(4) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C7 116.7(4) . . ? C5 C6 H6 121.7 . . ? C7 C6 H6 121.7 . . ? N2 C7 C6 131.7(3) . . ? N2 C7 C2 106.2(3) . . ? C6 C7 C2 122.0(3) . . ? N2 C8 C9 111.5(3) . . ? N2 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N2 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? O2 C9 O1 110.5(4) . . ? O2 C9 C8 106.7(3) . . ? O1 C9 C8 109.1(3) . . ? O2 C9 H9 110.1 . . ? O1 C9 H9 110.1 . . ? C8 C9 H9 110.1 . . ? O1 C10 H10A 109.5 . . ? O1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O2 C11 H11A 109.5 . . ? O2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 117.6(3) . . ? C14 C13 C12 122.3(3) . . ? C18 C13 C12 120.1(4) . . ? C14 C13 Ru1 70.22(18) . . ? C18 C13 Ru1 70.71(18) . . ? C12 C13 Ru1 127.9(3) . . ? C13 C14 C15 121.3(3) . . ? C13 C14 Ru1 72.36(18) . . ? C15 C14 Ru1 70.81(17) . . ? C13 C14 H14 119.4 . . ? C15 C14 H14 119.4 . . ? Ru1 C14 H14 130.1 . . ? C16 C15 C14 121.1(3) . . ? C16 C15 Ru1 72.42(18) . . ? C14 C15 Ru1 71.12(18) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? Ru1 C15 H15 129.5 . . ? C15 C16 C17 117.3(3) . . ? C15 C16 C19 123.5(3) . . ? C17 C16 C19 119.2(3) . . ? C15 C16 Ru1 70.05(19) . . ? C17 C16 Ru1 70.50(19) . . ? C19 C16 Ru1 131.1(2) . . ? C18 C17 C16 122.3(3) . . ? C18 C17 Ru1 72.0(2) . . ? C16 C17 Ru1 71.87(19) . . ? C18 C17 H17 118.8 . . ? C16 C17 H17 118.8 . . ? Ru1 C17 H17 130.1 . . ? C17 C18 C13 120.5(3) . . ? C17 C18 Ru1 71.1(2) . . ? C13 C18 Ru1 71.26(19) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? Ru1 C18 H18 130.6 . . ? C20 C19 C16 114.5(4) . . ? C20 C19 C21 112.0(4) . . ? C16 C19 C21 108.4(4) . . ? C20 C19 H19 107.2 . . ? C16 C19 H19 107.2 . . ? C21 C19 H19 107.2 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 N1 2.136(2) . ? Ru1 C15 2.171(3) . ? Ru1 C14 2.175(3) . ? Ru1 C17 2.183(3) . ? Ru1 C18 2.195(3) . ? Ru1 C16 2.201(3) . ? Ru1 C13 2.202(3) . ? Ru1 Cl1 2.4189(8) . ? Ru1 Cl2 2.4199(9) . ? O1 C9 1.396(5) . ? O1 C10 1.418(6) . ? O2 C9 1.379(5) . ? O2 C11 1.452(6) . ? N1 C1 1.320(4) . ? N1 C2 1.407(4) . ? N2 C1 1.345(4) . ? N2 C7 1.383(4) . ? N2 C8 1.462(4) . ? C1 H1 0.9300 . ? C2 C3 1.384(5) . ? C2 C7 1.403(4) . ? C3 C4 1.389(5) . ? C3 H3 0.9300 . ? C4 C5 1.401(6) . ? C4 H4 0.9300 . ? C5 C6 1.359(5) . ? C5 H5 0.9300 . ? C6 C7 1.402(5) . ? C6 H6 0.9300 . ? C8 C9 1.519(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9 0.9800 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.498(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.404(5) . ? C13 C18 1.433(5) . ? C14 C15 1.417(5) . ? C14 H14 0.9300 . ? C15 C16 1.407(5) . ? C15 H15 0.9300 . ? C16 C17 1.415(5) . ? C16 C19 1.516(5) . ? C17 C18 1.389(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.511(7) . ? C19 C21 1.532(6) . ? C19 H19 0.9800 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 N1 C1 N2 0.2(3) . . . . ? Ru1 N1 C1 N2 177.06(19) . . . . ? C7 N2 C1 N1 -0.1(3) . . . . ? C8 N2 C1 N1 -173.7(3) . . . . ? C1 N1 C2 C3 178.1(3) . . . . ? Ru1 N1 C2 C3 1.5(5) . . . . ? C1 N1 C2 C7 -0.2(3) . . . . ? Ru1 N1 C2 C7 -176.83(19) . . . . ? C7 C2 C3 C4 0.3(5) . . . . ? N1 C2 C3 C4 -177.9(3) . . . . ? C2 C3 C4 C5 -1.4(5) . . . . ? C3 C4 C5 C6 0.8(6) . . . . ? C4 C5 C6 C7 0.9(5) . . . . ? C1 N2 C7 C6 -179.8(3) . . . . ? C8 N2 C7 C6 -6.4(5) . . . . ? C1 N2 C7 C2 -0.1(3) . . . . ? C8 N2 C7 C2 173.4(3) . . . . ? C5 C6 C7 N2 177.8(3) . . . . ? C5 C6 C7 C2 -2.0(5) . . . . ? C3 C2 C7 N2 -178.4(3) . . . . ? N1 C2 C7 N2 0.2(3) . . . . ? C3 C2 C7 C6 1.4(5) . . . . ? N1 C2 C7 C6 180.0(3) . . . . ? C1 N2 C8 C9 81.2(4) . . . . ? C7 N2 C8 C9 -91.1(4) . . . . ? C11 O2 C9 O1 -67.8(6) . . . . ? C11 O2 C9 C8 173.7(5) . . . . ? C10 O1 C9 O2 138.9(4) . . . . ? C10 O1 C9 C8 -104.1(5) . . . . ? N2 C8 C9 O2 -64.5(4) . . . . ? N2 C8 C9 O1 176.1(3) . . . . ? C18 C13 C14 C15 -0.9(5) . . . . ? C12 C13 C14 C15 176.4(3) . . . . ? Ru1 C13 C14 C15 53.4(3) . . . . ? C18 C13 C14 Ru1 -54.3(3) . . . . ? C12 C13 C14 Ru1 123.0(3) . . . . ? C13 C14 C15 C16 0.5(5) . . . . ? Ru1 C14 C15 C16 54.6(3) . . . . ? C13 C14 C15 Ru1 -54.1(3) . . . . ? C14 C15 C16 C17 0.0(5) . . . . ? Ru1 C15 C16 C17 54.0(3) . . . . ? C14 C15 C16 C19 179.2(3) . . . . ? Ru1 C15 C16 C19 -126.8(3) . . . . ? C14 C15 C16 Ru1 -54.0(3) . . . . ? C15 C16 C17 C18 -0.2(5) . . . . ? C19 C16 C17 C18 -179.4(3) . . . . ? Ru1 C16 C17 C18 53.6(3) . . . . ? C15 C16 C17 Ru1 -53.8(3) . . . . ? C19 C16 C17 Ru1 127.0(3) . . . . ? C16 C17 C18 C13 -0.2(5) . . . . ? Ru1 C17 C18 C13 53.4(3) . . . . ? C16 C17 C18 Ru1 -53.6(3) . . . . ? C14 C13 C18 C17 0.7(5) . . . . ? C12 C13 C18 C17 -176.6(3) . . . . ? Ru1 C13 C18 C17 -53.3(3) . . . . ? C14 C13 C18 Ru1 54.1(3) . . . . ? C12 C13 C18 Ru1 -123.3(3) . . . . ? C15 C16 C19 C20 22.5(5) . . . . ? C17 C16 C19 C20 -158.4(4) . . . . ? Ru1 C16 C19 C20 -69.5(5) . . . . ? C15 C16 C19 C21 -103.3(4) . . . . ? C17 C16 C19 C21 75.9(4) . . . . ? Ru1 C16 C19 C21 164.7(3) . . . . ?