#------------------------------------------------------------------------------ #$Date: 2021-07-05 21:05:10 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267217 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060683.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_7060683 loop_ _publ_author_name '\,Ci\,cek, Metin' 'G\"urb\"uz, Nevin' '\"Ozdemir, Nam\?ik' '\"Ozdemir, \.Ismail' '\.Ispir, Esin' _publ_section_title ; Half-sandwich Ru(ii) arene complexes bearing benzimidazole ligands for the N-alkylation reaction of aniline with alcohols in a solvent-free medium ; _journal_issue 25 _journal_name_full 'New Journal of Chemistry' _journal_page_first 11075 _journal_page_last 11085 _journal_paper_doi 10.1039/D1NJ01539G _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C23 H32 Cl2 N2 O2 Ru' _chemical_formula_sum 'C23 H32 Cl2 N2 O2 Ru' _chemical_formula_weight 540.47 _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 30.6323(9) _cell_length_b 30.6323(9) _cell_length_c 14.2515(4) _cell_measurement_reflns_used 58790 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.17 _cell_measurement_theta_min 1.62 _cell_volume 11581.1(6) _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 1.000 _diffrn_measured_fraction_theta_max 0.989 _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 0.0818 _diffrn_reflns_av_unetI/netI 0.0391 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 49001 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.880 _diffrn_reflns_theta_min 2.097 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _exptl_absorpt_coefficient_mu 0.837 _exptl_absorpt_correction_T_max 0.9215 _exptl_absorpt_correction_T_min 0.6924 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.395 _exptl_crystal_description prism _exptl_crystal_F_000 5004 _exptl_crystal_size_max 0.770 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.467 _refine_diff_density_min -0.773 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 6081 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0376 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0492P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0831 _refine_ls_wR_factor_ref 0.0895 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4675 _reflns_number_total 6081 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01539g2.cif _cod_data_source_block namiko222 _cod_depositor_comments 'Adding full bibliography for 7060679--7060683.cif.' _cod_original_cell_volume 11581.1(8) _cod_database_code 7060683 _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 0.565 _shelx_estimated_absorpt_t_max 0.906 _shelx_res_file ; TITL namiko222 shelx.res created by SHELXL-2018/3 at 20:49:52 on 05-Feb-2021 CELL 0.71073 30.6323 30.6323 14.2515 90.000 90.000 120.000 ZERR 18.00 0.0009 0.0009 0.0004 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 414 576 36 36 36 18 MERG 2 FMAP 2 PLAN 3 SIZE 0.120 0.160 0.770 ACTA BOND $H CONF L.S. 20 TEMP 23.00 WGHT 0.049200 FVAR 0.07289 RU1 6 0.300715 0.182400 0.493076 11.00000 0.05517 0.03953 = 0.03415 0.00117 0.00098 0.02959 CL1 3 0.267522 0.092199 0.497535 11.00000 0.08812 0.04354 = 0.04849 0.00170 -0.00073 0.03726 CL2 3 0.383784 0.193521 0.463528 11.00000 0.06425 0.07250 = 0.04996 -0.00331 -0.00199 0.04570 O1 5 0.143167 0.089731 0.060160 11.00000 0.07561 0.10336 = 0.09377 -0.01315 -0.03647 0.03051 O2 5 0.153740 0.110679 0.215041 11.00000 0.08692 0.23771 = 0.09005 -0.01919 -0.00558 0.09977 N1 4 0.291809 0.174187 0.344830 11.00000 0.05155 0.04210 = 0.03423 0.00131 0.00030 0.02599 N2 4 0.257322 0.143399 0.205232 11.00000 0.04763 0.04174 = 0.04102 -0.00192 -0.00435 0.02268 C1 1 0.256651 0.135257 0.298875 11.00000 0.05245 0.04006 = 0.04128 0.00273 0.00088 0.02361 AFIX 43 H1 2 0.233641 0.105170 0.327659 11.00000 -1.20000 AFIX 0 C2 1 0.317954 0.211324 0.276902 11.00000 0.04672 0.04040 = 0.03607 0.00113 0.00147 0.02504 C3 1 0.358895 0.260142 0.284035 11.00000 0.05217 0.04593 = 0.04155 -0.00494 -0.00108 0.02611 AFIX 43 H3 2 0.374070 0.272848 0.341823 11.00000 -1.20000 AFIX 0 C4 1 0.376728 0.289569 0.203594 11.00000 0.05470 0.04373 = 0.05046 0.00069 0.00844 0.02338 C5 1 0.421641 0.342442 0.210271 11.00000 0.07082 0.05372 = 0.06746 -0.00244 0.01312 0.01384 AFIX 137 H5A 2 0.412317 0.366173 0.187642 11.00000 -1.50000 H5B 2 0.448783 0.344722 0.172908 11.00000 -1.50000 H5C 2 0.432273 0.349924 0.274490 11.00000 -1.50000 AFIX 0 C6 1 0.353625 0.269745 0.114808 11.00000 0.05834 0.04914 = 0.04214 0.00475 0.01052 0.03094 C7 1 0.372741 0.302415 0.027998 11.00000 0.08190 0.06604 = 0.05149 0.01584 0.01915 0.03235 AFIX 137 H7A 2 0.408691 0.317283 0.024150 11.00000 -1.50000 H7B 2 0.364210 0.328563 0.031438 11.00000 -1.50000 H7C 2 0.357453 0.282128 -0.026676 11.00000 -1.50000 AFIX 0 C8 1 0.314197 0.220706 0.107055 11.00000 0.05412 0.05258 = 0.03771 -0.00047 0.00111 0.03170 AFIX 43 H8 2 0.300068 0.207110 0.049007 11.00000 -1.20000 AFIX 0 C9 1 0.296258 0.192231 0.189145 11.00000 0.04636 0.04080 = 0.03976 -0.00091 0.00051 0.02693 C10 1 0.219981 0.109896 0.137147 11.00000 0.05776 0.04836 = 0.05121 -0.00847 -0.01197 0.02424 AFIX 23 H10A 2 0.206935 0.075169 0.156332 11.00000 -1.20000 H10B 2 0.235929 0.114380 0.076359 11.00000 -1.20000 AFIX 0 C11 1 0.176901 0.120518 0.128945 11.00000 0.06095 0.08110 = 0.07343 -0.01190 -0.02121 0.03539 AFIX 13 H11 2 0.190066 0.156002 0.112547 11.00000 -1.20000 AFIX 0 C12 1 0.148457 0.112584 -0.028225 11.00000 0.16492 0.21352 = 0.07951 -0.01020 -0.02911 0.11161 AFIX 137 H12A 2 0.118752 0.092521 -0.065032 11.00000 -1.50000 H12B 2 0.177277 0.115106 -0.059951 11.00000 -1.50000 H12C 2 0.152941 0.145679 -0.019848 11.00000 -1.50000 AFIX 0 C13 1 0.117281 0.127193 0.224178 11.00000 0.14223 0.41088 = 0.17412 -0.09952 -0.03389 0.19645 AFIX 137 H13A 2 0.120865 0.142543 0.284542 11.00000 -1.50000 H13B 2 0.083894 0.098736 0.218197 11.00000 -1.50000 H13C 2 0.122846 0.151278 0.175870 11.00000 -1.50000 AFIX 0 C14 1 0.389428 0.299065 0.562311 11.00000 0.07885 0.05430 = 0.09248 -0.01549 0.00230 0.02408 AFIX 137 H14A 2 0.411524 0.285740 0.572384 11.00000 -1.50000 H14B 2 0.394503 0.322836 0.610946 11.00000 -1.50000 H14C 2 0.396616 0.315625 0.502462 11.00000 -1.50000 AFIX 0 C15 1 0.335443 0.256633 0.564102 11.00000 0.06901 0.04069 = 0.05427 -0.00917 0.00052 0.03126 C16 1 0.300003 0.253379 0.497920 11.00000 0.08323 0.04210 = 0.04868 0.00687 0.01048 0.04360 AFIX 43 H16 2 0.309484 0.278493 0.452873 11.00000 -1.20000 AFIX 0 C17 1 0.249719 0.212063 0.499004 11.00000 0.06930 0.05932 = 0.04840 -0.00376 -0.00352 0.04824 AFIX 43 H17 2 0.227008 0.210346 0.453816 11.00000 -1.20000 AFIX 0 C18 1 0.233646 0.173811 0.566873 11.00000 0.05956 0.05288 = 0.05087 0.00072 0.00944 0.03490 C19 1 0.270339 0.177688 0.633755 11.00000 0.07559 0.05775 = 0.03550 0.00557 0.01232 0.04360 AFIX 43 H19 2 0.260883 0.152781 0.679223 11.00000 -1.20000 AFIX 0 C20 1 0.319786 0.217718 0.632598 11.00000 0.07442 0.05640 = 0.03865 -0.01107 -0.00581 0.04212 AFIX 43 H20 2 0.342748 0.219064 0.676833 11.00000 -1.20000 AFIX 0 C21 1 0.180452 0.128892 0.572716 11.00000 0.06558 0.05973 = 0.09078 -0.00372 0.01192 0.03223 AFIX 13 H21 2 0.183174 0.098930 0.585755 11.00000 -1.20000 AFIX 0 C22 1 0.150469 0.119181 0.482918 11.00000 0.06812 0.10267 = 0.12301 -0.02350 -0.00741 0.03563 AFIX 137 H22A 2 0.117322 0.090674 0.491436 11.00000 -1.50000 H22B 2 0.167200 0.112391 0.432854 11.00000 -1.50000 H22C 2 0.147892 0.148327 0.467580 11.00000 -1.50000 AFIX 0 C23 1 0.153127 0.136390 0.655603 11.00000 0.08651 0.09818 = 0.13428 -0.00029 0.05196 0.03280 AFIX 137 H23A 2 0.119838 0.107703 0.660864 11.00000 -1.50000 H23B 2 0.150865 0.166191 0.645619 11.00000 -1.50000 H23C 2 0.171535 0.139983 0.712331 11.00000 -1.50000 AFIX 0 HKLF 4 REM namiko222 REM wR2 = 0.0895, GooF = S = 1.017, Restrained GooF = 1.017 for all data REM R1 = 0.0376 for 4675 Fo > 4sig(Fo) and 0.0583 for all 6081 data REM 278 parameters refined using 0 restraints END WGHT 0.0492 0.0000 REM Highest difference peak 0.467, deepest hole -0.773, 1-sigma level 0.064 Q1 1 0.0000 0.0000 0.0000 10.16667 0.05 0.47 Q2 1 0.3028 0.1426 0.4907 11.00000 0.05 0.46 Q3 1 0.2714 0.1371 0.4961 11.00000 0.05 0.45 ; _shelx_res_checksum 38445 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 0.30072(2) 0.18240(2) 0.49308(2) 0.04032(8) Uani 1 1 d . . . . . Cl1 Cl 0.26752(3) 0.09220(3) 0.49754(5) 0.0581(2) Uani 1 1 d . . . . . Cl2 Cl 0.38378(3) 0.19352(3) 0.46353(5) 0.05712(19) Uani 1 1 d . . . . . O1 O 0.14317(11) 0.08973(12) 0.0602(2) 0.0972(9) Uani 1 1 d . . . . . O2 O 0.15374(13) 0.11068(19) 0.2150(3) 0.1300(15) Uani 1 1 d . . . . . N1 N 0.29181(8) 0.17419(8) 0.34483(15) 0.0415(5) Uani 1 1 d . . . . . N2 N 0.25732(8) 0.14340(8) 0.20523(16) 0.0433(5) Uani 1 1 d . . . . . C1 C 0.25665(10) 0.13526(10) 0.29887(19) 0.0444(6) Uani 1 1 d . . . . . H1 H 0.233641 0.105170 0.327659 0.053 Uiso 1 1 calc R U . . . C2 C 0.31795(10) 0.21132(9) 0.27690(18) 0.0396(5) Uani 1 1 d . . . . . C3 C 0.35890(10) 0.26014(10) 0.2840(2) 0.0458(6) Uani 1 1 d . . . . . H3 H 0.374070 0.272848 0.341823 0.055 Uiso 1 1 calc R U . . . C4 C 0.37673(11) 0.28957(10) 0.2036(2) 0.0502(7) Uani 1 1 d . . . . . C5 C 0.42164(14) 0.34244(13) 0.2103(3) 0.0717(10) Uani 1 1 d . . . . . H5A H 0.412317 0.366173 0.187642 0.108 Uiso 1 1 calc R U . . . H5B H 0.448783 0.344722 0.172908 0.108 Uiso 1 1 calc R U . . . H5C H 0.432273 0.349924 0.274490 0.108 Uiso 1 1 calc R U . . . C6 C 0.35362(11) 0.26975(11) 0.1148(2) 0.0481(6) Uani 1 1 d . . . . . C7 C 0.37274(15) 0.30241(14) 0.0280(2) 0.0685(9) Uani 1 1 d . . . . . H7A H 0.408691 0.317283 0.024150 0.103 Uiso 1 1 calc R U . . . H7B H 0.364210 0.328563 0.031438 0.103 Uiso 1 1 calc R U . . . H7C H 0.357453 0.282128 -0.026676 0.103 Uiso 1 1 calc R U . . . C8 C 0.31420(11) 0.22071(11) 0.1071(2) 0.0459(6) Uani 1 1 d . . . . . H8 H 0.300068 0.207110 0.049007 0.055 Uiso 1 1 calc R U . . . C9 C 0.29626(10) 0.19223(9) 0.18914(19) 0.0400(5) Uani 1 1 d . . . . . C10 C 0.21998(11) 0.10990(11) 0.1371(2) 0.0535(7) Uani 1 1 d . . . . . H10A H 0.206935 0.075169 0.156332 0.064 Uiso 1 1 calc R U . . . H10B H 0.235929 0.114380 0.076359 0.064 Uiso 1 1 calc R U . . . C11 C 0.17690(13) 0.12052(15) 0.1289(3) 0.0719(10) Uani 1 1 d . . . . . H11 H 0.190066 0.156002 0.112547 0.086 Uiso 1 1 calc R U . . . C12 C 0.1485(3) 0.1126(3) -0.0282(4) 0.145(2) Uani 1 1 d . . . . . H12A H 0.118752 0.092521 -0.065032 0.218 Uiso 1 1 calc R U . . . H12B H 0.177277 0.115106 -0.059951 0.218 Uiso 1 1 calc R U . . . H12C H 0.152941 0.145679 -0.019848 0.218 Uiso 1 1 calc R U . . . C13 C 0.1173(3) 0.1272(4) 0.2242(6) 0.217(5) Uani 1 1 d . . . . . H13A H 0.120865 0.142543 0.284542 0.325 Uiso 1 1 calc R U . . . H13B H 0.083894 0.098736 0.218197 0.325 Uiso 1 1 calc R U . . . H13C H 0.122846 0.151278 0.175870 0.325 Uiso 1 1 calc R U . . . C14 C 0.38943(15) 0.29907(14) 0.5623(3) 0.0793(11) Uani 1 1 d . . . . . H14A H 0.411524 0.285740 0.572384 0.119 Uiso 1 1 calc R U . . . H14B H 0.394503 0.322836 0.610946 0.119 Uiso 1 1 calc R U . . . H14C H 0.396616 0.315625 0.502462 0.119 Uiso 1 1 calc R U . . . C15 C 0.33544(12) 0.25663(10) 0.5641(2) 0.0530(7) Uani 1 1 d . . . . . C16 C 0.30000(13) 0.25338(10) 0.4979(2) 0.0526(7) Uani 1 1 d . . . . . H16 H 0.309484 0.278493 0.452873 0.063 Uiso 1 1 calc R U . . . C17 C 0.24972(12) 0.21206(11) 0.4990(2) 0.0519(7) Uani 1 1 d . . . . . H17 H 0.227008 0.210346 0.453816 0.062 Uiso 1 1 calc R U . . . C18 C 0.23365(12) 0.17381(11) 0.5669(2) 0.0514(7) Uani 1 1 d . . . . . C19 C 0.27034(12) 0.17769(12) 0.6338(2) 0.0517(7) Uani 1 1 d . . . . . H19 H 0.260883 0.152781 0.679223 0.062 Uiso 1 1 calc R U . . . C20 C 0.31979(12) 0.21772(11) 0.6326(2) 0.0523(7) Uani 1 1 d . . . . . H20 H 0.342748 0.219064 0.676833 0.063 Uiso 1 1 calc R U . . . C21 C 0.18045(14) 0.12889(14) 0.5727(3) 0.0716(10) Uani 1 1 d . . . . . H21 H 0.183174 0.098930 0.585755 0.086 Uiso 1 1 calc R U . . . C22 C 0.15047(17) 0.11918(19) 0.4829(4) 0.1011(15) Uani 1 1 d . . . . . H22A H 0.117322 0.090674 0.491436 0.152 Uiso 1 1 calc R U . . . H22B H 0.167200 0.112391 0.432854 0.152 Uiso 1 1 calc R U . . . H22C H 0.147892 0.148327 0.467580 0.152 Uiso 1 1 calc R U . . . C23 C 0.15313(18) 0.13639(19) 0.6556(4) 0.1123(18) Uani 1 1 d . . . . . H23A H 0.119838 0.107703 0.660864 0.168 Uiso 1 1 calc R U . . . H23B H 0.150865 0.166191 0.645619 0.168 Uiso 1 1 calc R U . . . H23C H 0.171535 0.139983 0.712331 0.168 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 0.05517(14) 0.03953(12) 0.03415(11) 0.00117(8) 0.00098(9) 0.02959(10) Cl1 0.0881(6) 0.0435(4) 0.0485(4) 0.0017(3) -0.0007(4) 0.0373(4) Cl2 0.0643(4) 0.0725(5) 0.0500(4) -0.0033(3) -0.0020(3) 0.0457(4) O1 0.0756(18) 0.103(2) 0.094(2) -0.0131(17) -0.0365(16) 0.0305(16) O2 0.087(2) 0.238(5) 0.090(2) -0.019(3) -0.0056(18) 0.100(3) N1 0.0516(12) 0.0421(11) 0.0342(11) 0.0013(9) 0.0003(9) 0.0260(10) N2 0.0476(12) 0.0417(11) 0.0410(12) -0.0019(9) -0.0043(9) 0.0227(10) C1 0.0524(15) 0.0401(13) 0.0413(15) 0.0027(11) 0.0009(12) 0.0236(12) C2 0.0467(13) 0.0404(13) 0.0361(13) 0.0011(10) 0.0015(11) 0.0250(11) C3 0.0522(15) 0.0459(14) 0.0415(14) -0.0049(11) -0.0011(12) 0.0261(13) C4 0.0547(16) 0.0437(14) 0.0505(17) 0.0007(12) 0.0084(13) 0.0234(13) C5 0.071(2) 0.0537(18) 0.067(2) -0.0024(16) 0.0131(18) 0.0138(16) C6 0.0583(16) 0.0491(15) 0.0421(15) 0.0048(12) 0.0105(12) 0.0309(14) C7 0.082(2) 0.066(2) 0.0515(19) 0.0158(16) 0.0192(17) 0.0324(18) C8 0.0541(15) 0.0526(15) 0.0377(14) -0.0005(11) 0.0011(12) 0.0317(13) C9 0.0464(13) 0.0408(13) 0.0398(14) -0.0009(10) 0.0005(11) 0.0269(11) C10 0.0578(17) 0.0484(15) 0.0512(17) -0.0085(13) -0.0120(14) 0.0242(14) C11 0.061(2) 0.081(2) 0.073(2) -0.0119(19) -0.0212(18) 0.0354(19) C12 0.165(6) 0.214(7) 0.080(4) -0.010(4) -0.029(4) 0.112(6) C13 0.142(6) 0.411(15) 0.174(8) -0.100(9) -0.034(5) 0.196(9) C14 0.079(2) 0.0543(19) 0.092(3) -0.0155(19) 0.002(2) 0.0241(18) C15 0.0690(19) 0.0407(14) 0.0543(18) -0.0092(12) 0.0005(15) 0.0313(14) C16 0.083(2) 0.0421(15) 0.0487(16) 0.0069(12) 0.0105(15) 0.0436(16) C17 0.0693(19) 0.0593(17) 0.0484(16) -0.0038(13) -0.0035(14) 0.0482(16) C18 0.0596(17) 0.0529(16) 0.0509(17) 0.0007(13) 0.0094(14) 0.0349(14) C19 0.076(2) 0.0577(17) 0.0355(14) 0.0056(12) 0.0123(13) 0.0436(16) C20 0.074(2) 0.0564(17) 0.0387(15) -0.0111(12) -0.0058(13) 0.0421(16) C21 0.066(2) 0.060(2) 0.091(3) -0.0037(18) 0.0119(19) 0.0322(17) C22 0.068(3) 0.103(3) 0.123(4) -0.024(3) -0.007(3) 0.036(2) C23 0.087(3) 0.098(3) 0.134(4) 0.000(3) 0.052(3) 0.033(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 C17 90.66(10) . . ? N1 Ru1 C19 151.38(11) . . ? C17 Ru1 C19 67.62(11) . . ? N1 Ru1 C16 94.84(10) . . ? C17 Ru1 C16 38.16(12) . . ? C19 Ru1 C16 79.69(11) . . ? N1 Ru1 C20 160.47(10) . . ? C17 Ru1 C20 80.11(11) . . ? C19 Ru1 C20 37.06(12) . . ? C16 Ru1 C20 67.32(11) . . ? N1 Ru1 C18 113.75(10) . . ? C17 Ru1 C18 37.50(11) . . ? C19 Ru1 C18 38.11(11) . . ? C16 Ru1 C18 68.37(11) . . ? C20 Ru1 C18 68.26(12) . . ? N1 Ru1 C15 122.83(10) . . ? C17 Ru1 C15 68.19(12) . . ? C19 Ru1 C15 67.58(12) . . ? C16 Ru1 C15 37.18(12) . . ? C20 Ru1 C15 37.68(11) . . ? C18 Ru1 C15 81.08(12) . . ? N1 Ru1 Cl1 86.29(6) . . ? C17 Ru1 Cl1 119.88(9) . . ? C19 Ru1 Cl1 88.77(8) . . ? C16 Ru1 Cl1 157.92(9) . . ? C20 Ru1 Cl1 113.23(8) . . ? C18 Ru1 Cl1 90.96(8) . . ? C15 Ru1 Cl1 150.63(9) . . ? N1 Ru1 Cl2 84.72(6) . . ? C17 Ru1 Cl2 150.74(9) . . ? C19 Ru1 Cl2 123.37(9) . . ? C16 Ru1 Cl2 113.37(9) . . ? C20 Ru1 Cl2 94.92(9) . . ? C18 Ru1 Cl2 161.47(9) . . ? C15 Ru1 Cl2 90.20(8) . . ? Cl1 Ru1 Cl2 88.70(3) . . ? C11 O1 C12 115.5(4) . . ? C11 O2 C13 114.1(5) . . ? C1 N1 C2 105.6(2) . . ? C1 N1 Ru1 126.89(18) . . ? C2 N1 Ru1 127.05(17) . . ? C1 N2 C9 106.6(2) . . ? C1 N2 C10 126.2(2) . . ? C9 N2 C10 126.6(2) . . ? N1 C1 N2 113.2(2) . . ? N1 C1 H1 123.4 . . ? N2 C1 H1 123.4 . . ? C3 C2 C9 119.9(2) . . ? C3 C2 N1 131.5(2) . . ? C9 C2 N1 108.6(2) . . ? C4 C3 C2 119.1(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C6 120.3(3) . . ? C3 C4 C5 119.6(3) . . ? C6 C4 C5 120.1(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C8 C6 C4 120.7(3) . . ? C8 C6 C7 119.5(3) . . ? C4 C6 C7 119.8(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 C9 117.9(3) . . ? C6 C8 H8 121.0 . . ? C9 C8 H8 121.0 . . ? N2 C9 C8 132.0(3) . . ? N2 C9 C2 106.0(2) . . ? C8 C9 C2 122.1(2) . . ? N2 C10 C11 111.2(3) . . ? N2 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? N2 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? O2 C11 O1 110.7(3) . . ? O2 C11 C10 107.1(3) . . ? O1 C11 C10 109.9(3) . . ? O2 C11 H11 109.7 . . ? O1 C11 H11 109.7 . . ? C10 C11 H11 109.7 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C20 118.4(3) . . ? C16 C15 C14 121.7(3) . . ? C20 C15 C14 119.8(3) . . ? C16 C15 Ru1 70.28(16) . . ? C20 C15 Ru1 70.52(16) . . ? C14 C15 Ru1 129.3(2) . . ? C15 C16 C17 120.7(3) . . ? C15 C16 Ru1 72.54(15) . . ? C17 C16 Ru1 70.15(14) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? Ru1 C16 H16 130.3 . . ? C18 C17 C16 121.4(3) . . ? C18 C17 Ru1 72.69(16) . . ? C16 C17 Ru1 71.68(16) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? Ru1 C17 H17 128.7 . . ? C17 C18 C19 117.1(3) . . ? C17 C18 C21 124.2(3) . . ? C19 C18 C21 118.7(3) . . ? C17 C18 Ru1 69.81(16) . . ? C19 C18 Ru1 70.22(16) . . ? C21 C18 Ru1 130.3(2) . . ? C20 C19 C18 121.9(3) . . ? C20 C19 Ru1 72.02(16) . . ? C18 C19 Ru1 71.67(16) . . ? C20 C19 H19 119.1 . . ? C18 C19 H19 119.1 . . ? Ru1 C19 H19 129.9 . . ? C19 C20 C15 120.5(3) . . ? C19 C20 Ru1 70.92(16) . . ? C15 C20 Ru1 71.80(16) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? Ru1 C20 H20 130.1 . . ? C22 C21 C18 113.7(3) . . ? C22 C21 C23 111.0(4) . . ? C18 C21 C23 109.0(3) . . ? C22 C21 H21 107.7 . . ? C18 C21 H21 107.7 . . ? C23 C21 H21 107.7 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 2.129(2) . ? Ru1 C17 2.166(3) . ? Ru1 C19 2.184(3) . ? Ru1 C16 2.186(2) . ? Ru1 C20 2.199(3) . ? Ru1 C18 2.204(3) . ? Ru1 C15 2.215(3) . ? Ru1 Cl1 2.4213(7) . ? Ru1 Cl2 2.4293(8) . ? O1 C11 1.394(4) . ? O1 C12 1.411(7) . ? O2 C11 1.373(5) . ? O2 C13 1.444(7) . ? N1 C1 1.314(3) . ? N1 C2 1.401(3) . ? N2 C1 1.356(3) . ? N2 C9 1.389(3) . ? N2 C10 1.459(3) . ? C1 H1 0.9300 . ? C2 C3 1.394(4) . ? C2 C9 1.400(4) . ? C3 C4 1.390(4) . ? C3 H3 0.9300 . ? C4 C6 1.429(4) . ? C4 C5 1.516(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C8 1.383(4) . ? C6 C7 1.513(4) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.397(4) . ? C8 H8 0.9300 . ? C10 C11 1.513(5) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11 0.9800 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.508(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.403(4) . ? C15 C20 1.426(4) . ? C16 C17 1.423(4) . ? C16 H16 0.9300 . ? C17 C18 1.405(4) . ? C17 H17 0.9300 . ? C18 C19 1.433(4) . ? C18 C21 1.521(5) . ? C19 C20 1.393(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.515(6) . ? C21 C23 1.530(6) . ? C21 H21 0.9800 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 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 172.83(17) . . . . ? C9 N2 C1 N1 -0.5(3) . . . . ? C10 N2 C1 N1 -172.7(2) . . . . ? C1 N1 C2 C3 -179.7(3) . . . . ? Ru1 N1 C2 C3 7.7(4) . . . . ? C1 N1 C2 C9 0.2(3) . . . . ? Ru1 N1 C2 C9 -172.45(16) . . . . ? C9 C2 C3 C4 1.6(4) . . . . ? N1 C2 C3 C4 -178.6(3) . . . . ? C2 C3 C4 C6 -0.6(4) . . . . ? C2 C3 C4 C5 -179.2(3) . . . . ? C3 C4 C6 C8 -1.8(4) . . . . ? C5 C4 C6 C8 176.8(3) . . . . ? C3 C4 C6 C7 178.9(3) . . . . ? C5 C4 C6 C7 -2.5(4) . . . . ? C4 C6 C8 C9 3.0(4) . . . . ? C7 C6 C8 C9 -177.6(3) . . . . ? C1 N2 C9 C8 -179.8(3) . . . . ? C10 N2 C9 C8 -7.6(4) . . . . ? C1 N2 C9 C2 0.5(3) . . . . ? C10 N2 C9 C2 172.8(2) . . . . ? C6 C8 C9 N2 178.3(3) . . . . ? C6 C8 C9 C2 -2.1(4) . . . . ? C3 C2 C9 N2 179.4(2) . . . . ? N1 C2 C9 N2 -0.4(3) . . . . ? C3 C2 C9 C8 -0.2(4) . . . . ? N1 C2 C9 C8 179.9(2) . . . . ? C1 N2 C10 C11 87.5(4) . . . . ? C9 N2 C10 C11 -83.2(4) . . . . ? C13 O2 C11 O1 -70.5(6) . . . . ? C13 O2 C11 C10 169.8(5) . . . . ? C12 O1 C11 O2 142.9(5) . . . . ? C12 O1 C11 C10 -99.0(5) . . . . ? N2 C10 C11 O2 -62.7(4) . . . . ? N2 C10 C11 O1 177.0(3) . . . . ? C20 C15 C16 C17 -0.3(4) . . . . ? C14 C15 C16 C17 177.8(3) . . . . ? Ru1 C15 C16 C17 53.1(2) . . . . ? C20 C15 C16 Ru1 -53.4(2) . . . . ? C14 C15 C16 Ru1 124.7(3) . . . . ? C15 C16 C17 C18 1.1(4) . . . . ? Ru1 C16 C17 C18 55.3(2) . . . . ? C15 C16 C17 Ru1 -54.2(2) . . . . ? C16 C17 C18 C19 -1.2(4) . . . . ? Ru1 C17 C18 C19 53.6(2) . . . . ? C16 C17 C18 C21 179.4(3) . . . . ? Ru1 C17 C18 C21 -125.7(3) . . . . ? C16 C17 C18 Ru1 -54.8(2) . . . . ? C17 C18 C19 C20 0.5(4) . . . . ? C21 C18 C19 C20 179.9(3) . . . . ? Ru1 C18 C19 C20 53.9(2) . . . . ? C17 C18 C19 Ru1 -53.4(2) . . . . ? C21 C18 C19 Ru1 126.0(3) . . . . ? C18 C19 C20 C15 0.3(4) . . . . ? Ru1 C19 C20 C15 54.1(2) . . . . ? C18 C19 C20 Ru1 -53.8(2) . . . . ? C16 C15 C20 C19 -0.4(4) . . . . ? C14 C15 C20 C19 -178.5(3) . . . . ? Ru1 C15 C20 C19 -53.6(2) . . . . ? C16 C15 C20 Ru1 53.2(2) . . . . ? C14 C15 C20 Ru1 -124.9(3) . . . . ? C17 C18 C21 C22 18.5(5) . . . . ? C19 C18 C21 C22 -160.8(3) . . . . ? Ru1 C18 C21 C22 -73.2(4) . . . . ? C17 C18 C21 C23 -105.8(4) . . . . ? C19 C18 C21 C23 74.8(4) . . . . ? Ru1 C18 C21 C23 162.5(3) . . . . ?