#------------------------------------------------------------------------------ #$Date: 2021-05-14 06:25:59 +0300 (Fri, 14 May 2021) $ #$Revision: 265209 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060682.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_7060682 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 'C30 H30 Cl2 N2 Ru' _chemical_formula_sum 'C30 H30 Cl2 N2 Ru' _chemical_formula_weight 590.53 _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 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 103.766(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.4953(7) _cell_length_b 13.5037(6) _cell_length_c 15.3680(9) _cell_measurement_reflns_used 36475 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.18 _cell_measurement_theta_min 1.81 _cell_volume 2720.2(2) _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 0.994 _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method '\w scans' _diffrn_radiation_collimation '0.5 mm diameter, multiple pinhole' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0869 _diffrn_reflns_av_unetI/netI 0.0528 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 31645 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.770 _diffrn_reflns_theta_min 2.034 _diffrn_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_T_max 0.9406 _exptl_absorpt_correction_T_min 0.7977 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_crystal_colour brown _exptl_crystal_density_diffrn 1.442 _exptl_crystal_description prism _exptl_crystal_F_000 1208 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.643 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.064 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 319 _refine_ls_number_reflns 6378 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.010 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0362 _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^)+(0.0309P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.0734 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4981 _reflns_number_total 6378 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01539g2.cif _cod_data_source_block namiko216 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7060682 _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 0.721 _shelx_estimated_absorpt_t_max 0.939 _shelx_res_file ; TITL namiko216 shelx.res created by SHELXL-2018/3 at 21:50:11 on 05-Feb-2021 CELL 0.71073 13.4953 13.5037 15.3680 90.000 103.766 90.000 ZERR 4.00 0.0007 0.0006 0.0009 0.000 0.004 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H CL N RU UNIT 120 120 8 8 4 MERG 2 FMAP 2 PLAN 3 SIZE 0.080 0.110 0.440 ACTA BOND $H CONF L.S. 20 TEMP 23.00 WGHT 0.030900 FVAR 0.32906 RU1 5 0.597780 0.732601 0.767210 11.00000 0.02709 0.03058 = 0.02890 0.00230 0.00749 0.00069 CL1 3 0.575565 0.679417 0.911140 11.00000 0.05248 0.06680 = 0.03230 0.01196 0.00938 -0.00381 CL2 3 0.644215 0.563581 0.738861 11.00000 0.04261 0.03400 = 0.06745 -0.00412 0.01306 0.00277 N1 4 0.444716 0.684465 0.715954 11.00000 0.03038 0.03898 = 0.03079 0.00081 0.00895 -0.00023 N2 4 0.279873 0.659300 0.708087 11.00000 0.02869 0.04178 = 0.03306 -0.00089 0.00835 0.00047 C1 1 0.371073 0.689609 0.758706 11.00000 0.03276 0.04235 = 0.02935 -0.00226 0.00893 -0.00063 AFIX 43 H1 2 0.380720 0.711720 0.817440 11.00000 -1.20000 AFIX 0 C2 1 0.399701 0.646804 0.630650 11.00000 0.03527 0.03616 = 0.03152 0.00259 0.00741 0.00011 C3 1 0.441364 0.623798 0.557976 11.00000 0.04674 0.06091 = 0.03786 -0.00412 0.01794 -0.00245 AFIX 43 H3 2 0.510317 0.633370 0.560867 11.00000 -1.20000 AFIX 0 C4 1 0.376445 0.586437 0.481975 11.00000 0.06689 0.06895 = 0.03816 -0.01050 0.01896 0.00094 AFIX 43 H4 2 0.402311 0.569948 0.432923 11.00000 -1.20000 AFIX 0 C5 1 0.272847 0.572822 0.477017 11.00000 0.06106 0.06559 = 0.03185 -0.00781 0.00259 -0.00399 AFIX 43 H5 2 0.231527 0.547383 0.424560 11.00000 -1.20000 AFIX 0 C6 1 0.229490 0.595791 0.547268 11.00000 0.04139 0.04720 = 0.03697 0.00006 0.00283 -0.00301 AFIX 43 H6 2 0.160098 0.587619 0.543142 11.00000 -1.20000 AFIX 0 C7 1 0.295496 0.631951 0.624832 11.00000 0.03587 0.03185 = 0.03211 0.00240 0.00759 0.00233 C8 1 0.181096 0.655788 0.733657 11.00000 0.02508 0.03987 = 0.03548 0.00124 0.00624 -0.00047 AFIX 13 H8 2 0.141416 0.602412 0.698508 11.00000 -1.20000 AFIX 0 C9 1 0.120617 0.750879 0.707482 11.00000 0.03194 0.05002 = 0.03580 0.00923 0.00988 0.00394 C10 1 0.164826 0.843717 0.727785 11.00000 0.04030 0.04831 = 0.05286 0.00848 0.01266 0.00274 AFIX 43 H10 2 0.233506 0.848370 0.756766 11.00000 -1.20000 AFIX 0 C11 1 0.107994 0.929103 0.705439 11.00000 0.06782 0.04733 = 0.07169 0.01696 0.02723 0.01045 AFIX 43 H11 2 0.138186 0.990665 0.720286 11.00000 -1.20000 AFIX 0 C12 1 0.006314 0.923012 0.661038 11.00000 0.05791 0.06493 = 0.08135 0.03011 0.02519 0.02505 AFIX 43 H12 2 -0.031526 0.980487 0.644765 11.00000 -1.20000 AFIX 0 C13 1 -0.038544 0.832597 0.641083 11.00000 0.03569 0.08946 = 0.06884 0.02555 0.01053 0.01841 AFIX 43 H13 2 -0.107373 0.828808 0.612392 11.00000 -1.20000 AFIX 0 C14 1 0.017968 0.745683 0.663351 11.00000 0.03442 0.06412 = 0.05215 0.00962 0.00805 0.00105 AFIX 43 H14 2 -0.012982 0.684415 0.648697 11.00000 -1.20000 AFIX 0 C15 1 0.196839 0.626771 0.832168 11.00000 0.02636 0.03406 = 0.03815 0.00142 0.00960 -0.00277 C16 1 0.156631 0.680421 0.892868 11.00000 0.04734 0.03923 = 0.04742 0.00332 0.01812 0.00950 AFIX 43 H16 2 0.121491 0.739032 0.874967 11.00000 -1.20000 AFIX 0 C17 1 0.168739 0.646817 0.980206 11.00000 0.06334 0.05407 = 0.04336 -0.00251 0.02277 0.00443 AFIX 43 H17 2 0.140918 0.682765 1.020232 11.00000 -1.20000 AFIX 0 C18 1 0.221410 0.561006 1.007988 11.00000 0.05061 0.05577 = 0.03679 0.00608 0.00965 -0.00708 AFIX 43 H18 2 0.229410 0.539017 1.066600 11.00000 -1.20000 AFIX 0 C19 1 0.262291 0.507730 0.948621 11.00000 0.04809 0.04328 = 0.05544 0.01265 0.00927 0.01038 AFIX 43 H19 2 0.298557 0.449888 0.967248 11.00000 -1.20000 AFIX 0 C20 1 0.249542 0.539994 0.861680 11.00000 0.04575 0.03880 = 0.05145 0.00193 0.01664 0.00840 AFIX 43 H20 2 0.276740 0.502982 0.821907 11.00000 -1.20000 AFIX 0 C21 1 0.473314 0.889022 0.606455 11.00000 0.05811 0.05213 = 0.05170 0.01245 0.00193 0.01103 AFIX 137 H21A 2 0.478645 0.956086 0.587345 11.00000 -1.50000 H21B 2 0.414310 0.882607 0.630702 11.00000 -1.50000 H21C 2 0.466969 0.845264 0.556196 11.00000 -1.50000 AFIX 0 C22 1 0.566520 0.862792 0.676532 11.00000 0.04438 0.03317 = 0.04060 0.00995 0.00821 0.00003 C23 1 0.575258 0.893501 0.766966 11.00000 0.04396 0.02977 = 0.05649 0.00198 0.01515 0.00388 AFIX 43 H23 2 0.523631 0.931078 0.781337 11.00000 -1.20000 AFIX 0 C24 1 0.660806 0.867493 0.833988 11.00000 0.04872 0.03411 = 0.04427 -0.00693 0.00662 -0.00416 AFIX 43 H24 2 0.664398 0.887966 0.892436 11.00000 -1.20000 AFIX 0 C25 1 0.742819 0.810728 0.816121 11.00000 0.03521 0.03597 = 0.05185 0.00202 0.00752 -0.00796 C26 1 0.731921 0.779258 0.726140 11.00000 0.03595 0.03825 = 0.05415 0.00686 0.01886 -0.00186 AFIX 43 H26 2 0.782941 0.740573 0.712042 11.00000 -1.20000 AFIX 0 C27 1 0.645749 0.804932 0.657123 11.00000 0.04418 0.04201 = 0.03719 0.00831 0.01526 -0.00385 AFIX 43 H27 2 0.641384 0.783569 0.598801 11.00000 -1.20000 AFIX 0 C28 1 0.833910 0.783657 0.891956 11.00000 0.04292 0.05920 = 0.05762 -0.00339 0.00014 -0.00020 AFIX 13 H28 2 0.811389 0.786824 0.947994 11.00000 -1.20000 AFIX 0 C29 1 0.873962 0.680541 0.884453 11.00000 0.05700 0.05839 = 0.08566 0.00710 -0.01963 0.00309 AFIX 137 H29A 2 0.819020 0.633836 0.877658 11.00000 -1.50000 H29B 2 0.925316 0.665208 0.937636 11.00000 -1.50000 H29C 2 0.903049 0.676934 0.833289 11.00000 -1.50000 AFIX 0 C30 1 0.917715 0.861345 0.897676 11.00000 0.04423 0.06219 = 0.11951 -0.01215 -0.01483 -0.00625 AFIX 137 H30A 2 0.975248 0.844440 0.945385 11.00000 -1.50000 H30B 2 0.892182 0.925162 0.909179 11.00000 -1.50000 H30C 2 0.938308 0.863188 0.842054 11.00000 -1.50000 AFIX 0 HKLF 4 REM namiko216 REM wR2 = 0.0734, GooF = S = 1.010, Restrained GooF = 1.010 for all data REM R1 = 0.0362 for 4981 Fo > 4sig(Fo) and 0.0572 for all 6378 data REM 319 parameters refined using 0 restraints END WGHT 0.0309 0.0000 REM Highest difference peak 0.643, deepest hole -0.381, 1-sigma level 0.064 Q1 1 0.5573 0.6756 0.7806 11.00000 0.05 0.64 Q2 1 0.6416 0.7929 0.7598 11.00000 0.05 0.45 Q3 1 0.5591 0.7957 0.7860 11.00000 0.05 0.44 ; _shelx_res_checksum 89066 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 0.59778(2) 0.73260(2) 0.76721(2) 0.02872(6) Uani 1 1 d . . . . . Cl1 Cl 0.57557(6) 0.67942(6) 0.91114(4) 0.05065(18) Uani 1 1 d . . . . . Cl2 Cl 0.64422(5) 0.56358(5) 0.73886(5) 0.04803(17) Uani 1 1 d . . . . . N1 N 0.44472(15) 0.68447(15) 0.71595(13) 0.0331(4) Uani 1 1 d . . . . . N2 N 0.27987(15) 0.65930(16) 0.70809(14) 0.0343(4) Uani 1 1 d . . . . . C1 C 0.37107(19) 0.6896(2) 0.75871(17) 0.0346(5) Uani 1 1 d . . . . . H1 H 0.380720 0.711720 0.817440 0.041 Uiso 1 1 calc R U . . . C2 C 0.39970(19) 0.64680(19) 0.63065(16) 0.0344(5) Uani 1 1 d . . . . . C3 C 0.4414(2) 0.6238(2) 0.55798(19) 0.0472(7) Uani 1 1 d . . . . . H3 H 0.510317 0.633370 0.560867 0.057 Uiso 1 1 calc R U . . . C4 C 0.3764(3) 0.5864(3) 0.4820(2) 0.0569(8) Uani 1 1 d . . . . . H4 H 0.402311 0.569948 0.432923 0.068 Uiso 1 1 calc R U . . . C5 C 0.2728(3) 0.5728(3) 0.47702(19) 0.0543(8) Uani 1 1 d . . . . . H5 H 0.231527 0.547383 0.424560 0.065 Uiso 1 1 calc R U . . . C6 C 0.2295(2) 0.5958(2) 0.54727(18) 0.0429(6) Uani 1 1 d . . . . . H6 H 0.160098 0.587619 0.543142 0.052 Uiso 1 1 calc R U . . . C7 C 0.29550(19) 0.63195(18) 0.62483(17) 0.0334(5) Uani 1 1 d . . . . . C8 C 0.18110(18) 0.65579(19) 0.73366(17) 0.0336(5) Uani 1 1 d . . . . . H8 H 0.141416 0.602412 0.698508 0.040 Uiso 1 1 calc R U . . . C9 C 0.12062(19) 0.7509(2) 0.70748(17) 0.0389(6) Uani 1 1 d . . . . . C10 C 0.1648(2) 0.8437(2) 0.7278(2) 0.0469(7) Uani 1 1 d . . . . . H10 H 0.233506 0.848370 0.756766 0.056 Uiso 1 1 calc R U . . . C11 C 0.1080(3) 0.9291(3) 0.7054(2) 0.0605(9) Uani 1 1 d . . . . . H11 H 0.138186 0.990665 0.720286 0.073 Uiso 1 1 calc R U . . . C12 C 0.0063(3) 0.9230(3) 0.6610(3) 0.0666(10) Uani 1 1 d . . . . . H12 H -0.031526 0.980487 0.644765 0.080 Uiso 1 1 calc R U . . . C13 C -0.0385(2) 0.8326(3) 0.6411(2) 0.0650(10) Uani 1 1 d . . . . . H13 H -0.107373 0.828808 0.612392 0.078 Uiso 1 1 calc R U . . . C14 C 0.0180(2) 0.7457(2) 0.6634(2) 0.0506(7) Uani 1 1 d . . . . . H14 H -0.012982 0.684415 0.648697 0.061 Uiso 1 1 calc R U . . . C15 C 0.19684(18) 0.62677(18) 0.83217(17) 0.0325(5) Uani 1 1 d . . . . . C16 C 0.1566(2) 0.6804(2) 0.89287(19) 0.0435(6) Uani 1 1 d . . . . . H16 H 0.121491 0.739032 0.874967 0.052 Uiso 1 1 calc R U . . . C17 C 0.1687(3) 0.6468(2) 0.9802(2) 0.0519(7) Uani 1 1 d . . . . . H17 H 0.140918 0.682765 1.020232 0.062 Uiso 1 1 calc R U . . . C18 C 0.2214(2) 0.5610(2) 1.0080(2) 0.0478(7) Uani 1 1 d . . . . . H18 H 0.229410 0.539017 1.066600 0.057 Uiso 1 1 calc R U . . . C19 C 0.2623(2) 0.5077(2) 0.9486(2) 0.0495(7) Uani 1 1 d . . . . . H19 H 0.298557 0.449888 0.967248 0.059 Uiso 1 1 calc R U . . . C20 C 0.2495(2) 0.5400(2) 0.8617(2) 0.0445(6) Uani 1 1 d . . . . . H20 H 0.276740 0.502982 0.821907 0.053 Uiso 1 1 calc R U . . . C21 C 0.4733(3) 0.8890(3) 0.6065(2) 0.0559(8) Uani 1 1 d . . . . . H21A H 0.478645 0.956086 0.587345 0.084 Uiso 1 1 calc R U . . . H21B H 0.414310 0.882607 0.630702 0.084 Uiso 1 1 calc R U . . . H21C H 0.466969 0.845264 0.556196 0.084 Uiso 1 1 calc R U . . . C22 C 0.5665(2) 0.86279(19) 0.67653(18) 0.0397(6) Uani 1 1 d . . . . . C23 C 0.5753(2) 0.89350(19) 0.7670(2) 0.0429(6) Uani 1 1 d . . . . . H23 H 0.523631 0.931078 0.781337 0.051 Uiso 1 1 calc R U . . . C24 C 0.6608(2) 0.8675(2) 0.8340(2) 0.0431(6) Uani 1 1 d . . . . . H24 H 0.664398 0.887966 0.892436 0.052 Uiso 1 1 calc R U . . . C25 C 0.7428(2) 0.8107(2) 0.81612(19) 0.0415(6) Uani 1 1 d . . . . . C26 C 0.7319(2) 0.7793(2) 0.72614(19) 0.0414(6) Uani 1 1 d . . . . . H26 H 0.782941 0.740573 0.712042 0.050 Uiso 1 1 calc R U . . . C27 C 0.6457(2) 0.8049(2) 0.65712(18) 0.0402(6) Uani 1 1 d . . . . . H27 H 0.641384 0.783569 0.598801 0.048 Uiso 1 1 calc R U . . . C28 C 0.8339(2) 0.7837(3) 0.8920(2) 0.0552(8) Uani 1 1 d . . . . . H28 H 0.811389 0.786824 0.947994 0.066 Uiso 1 1 calc R U . . . C29 C 0.8740(3) 0.6805(3) 0.8845(3) 0.0732(11) Uani 1 1 d . . . . . H29A H 0.819020 0.633836 0.877658 0.110 Uiso 1 1 calc R U . . . H29B H 0.925316 0.665208 0.937636 0.110 Uiso 1 1 calc R U . . . H29C H 0.903049 0.676934 0.833289 0.110 Uiso 1 1 calc R U . . . C30 C 0.9177(3) 0.8613(3) 0.8977(3) 0.0811(13) Uani 1 1 d . . . . . H30A H 0.975248 0.844440 0.945385 0.122 Uiso 1 1 calc R U . . . H30B H 0.892182 0.925162 0.909179 0.122 Uiso 1 1 calc R U . . . H30C H 0.938308 0.863188 0.842054 0.122 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 0.02709(9) 0.03058(9) 0.02890(9) 0.00230(9) 0.00749(6) 0.00069(9) Cl1 0.0525(4) 0.0668(5) 0.0323(3) 0.0120(3) 0.0094(3) -0.0038(3) Cl2 0.0426(4) 0.0340(3) 0.0675(5) -0.0041(3) 0.0131(3) 0.0028(3) N1 0.0304(10) 0.0390(11) 0.0308(10) 0.0008(9) 0.0089(9) -0.0002(9) N2 0.0287(10) 0.0418(11) 0.0331(11) -0.0009(9) 0.0084(9) 0.0005(9) C1 0.0328(12) 0.0423(14) 0.0294(12) -0.0023(10) 0.0089(10) -0.0006(11) C2 0.0353(13) 0.0362(13) 0.0315(12) 0.0026(10) 0.0074(10) 0.0001(10) C3 0.0467(16) 0.0609(18) 0.0379(15) -0.0041(13) 0.0179(13) -0.0025(14) C4 0.067(2) 0.069(2) 0.0382(16) -0.0105(14) 0.0190(15) 0.0009(17) C5 0.061(2) 0.066(2) 0.0319(15) -0.0078(13) 0.0026(13) -0.0040(16) C6 0.0414(15) 0.0472(16) 0.0370(14) 0.0001(12) 0.0028(12) -0.0030(12) C7 0.0359(13) 0.0319(12) 0.0321(12) 0.0024(9) 0.0076(10) 0.0023(10) C8 0.0251(11) 0.0399(14) 0.0355(13) 0.0012(10) 0.0062(10) -0.0005(10) C9 0.0319(12) 0.0500(18) 0.0358(12) 0.0092(11) 0.0099(10) 0.0039(11) C10 0.0403(15) 0.0483(17) 0.0529(17) 0.0085(13) 0.0127(13) 0.0027(13) C11 0.068(2) 0.0473(17) 0.072(2) 0.0170(16) 0.0272(19) 0.0104(16) C12 0.058(2) 0.065(2) 0.081(3) 0.0301(19) 0.0252(19) 0.0250(18) C13 0.0357(16) 0.089(3) 0.069(2) 0.0255(19) 0.0105(15) 0.0184(17) C14 0.0344(14) 0.064(2) 0.0522(16) 0.0096(14) 0.0081(12) 0.0010(13) C15 0.0264(11) 0.0341(13) 0.0381(13) 0.0014(10) 0.0096(10) -0.0028(10) C16 0.0473(16) 0.0392(15) 0.0474(16) 0.0033(12) 0.0181(13) 0.0095(12) C17 0.063(2) 0.0541(18) 0.0434(16) -0.0025(13) 0.0228(15) 0.0044(15) C18 0.0506(17) 0.0558(18) 0.0368(15) 0.0061(13) 0.0097(13) -0.0071(14) C19 0.0481(17) 0.0433(16) 0.0554(18) 0.0126(13) 0.0093(14) 0.0104(13) C20 0.0457(16) 0.0388(15) 0.0514(17) 0.0019(12) 0.0166(13) 0.0084(12) C21 0.058(2) 0.0521(18) 0.0517(18) 0.0124(14) 0.0019(15) 0.0110(15) C22 0.0444(15) 0.0332(13) 0.0406(14) 0.0099(11) 0.0082(12) 0.0000(11) C23 0.0440(16) 0.0298(13) 0.0565(17) 0.0020(12) 0.0151(14) 0.0039(11) C24 0.0487(16) 0.0341(14) 0.0443(15) -0.0069(11) 0.0066(13) -0.0042(12) C25 0.0352(14) 0.0360(14) 0.0519(16) 0.0020(12) 0.0075(12) -0.0080(11) C26 0.0359(13) 0.0383(14) 0.0541(16) 0.0069(12) 0.0189(12) -0.0019(11) C27 0.0442(15) 0.0420(14) 0.0372(14) 0.0083(11) 0.0153(12) -0.0038(12) C28 0.0429(16) 0.059(2) 0.0576(18) -0.0034(15) 0.0001(14) -0.0002(14) C29 0.057(2) 0.058(2) 0.086(3) 0.0071(19) -0.0196(19) 0.0031(18) C30 0.0442(19) 0.062(2) 0.120(4) -0.012(2) -0.015(2) -0.0062(17) 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' 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 C26 142.35(9) . . ? N1 Ru1 C24 132.05(10) . . ? C26 Ru1 C24 68.21(11) . . ? N1 Ru1 C27 106.89(9) . . ? C26 Ru1 C27 38.23(10) . . ? C24 Ru1 C27 80.51(11) . . ? N1 Ru1 C25 169.01(9) . . ? C26 Ru1 C25 38.18(11) . . ? C24 Ru1 C25 38.20(11) . . ? C27 Ru1 C25 69.20(11) . . ? N1 Ru1 C23 100.36(10) . . ? C26 Ru1 C23 80.51(10) . . ? C24 Ru1 C23 37.39(11) . . ? C27 Ru1 C23 67.77(10) . . ? C25 Ru1 C23 68.66(11) . . ? N1 Ru1 C22 89.25(9) . . ? C26 Ru1 C22 68.35(10) . . ? C24 Ru1 C22 68.01(11) . . ? C27 Ru1 C22 37.42(10) . . ? C25 Ru1 C22 81.66(10) . . ? C23 Ru1 C22 37.74(10) . . ? N1 Ru1 Cl1 85.81(6) . . ? C26 Ru1 Cl1 130.86(8) . . ? C24 Ru1 Cl1 86.35(8) . . ? C27 Ru1 Cl1 165.85(8) . . ? C25 Ru1 Cl1 97.15(8) . . ? C23 Ru1 Cl1 104.43(8) . . ? C22 Ru1 Cl1 139.91(7) . . ? N1 Ru1 Cl2 85.18(6) . . ? C26 Ru1 Cl2 87.22(8) . . ? C24 Ru1 Cl2 141.79(8) . . ? C27 Ru1 Cl2 98.31(8) . . ? C25 Ru1 Cl2 105.41(8) . . ? C23 Ru1 Cl2 165.95(7) . . ? C22 Ru1 Cl2 130.45(8) . . ? Cl1 Ru1 Cl2 88.76(3) . . ? C1 N1 C2 106.0(2) . . ? C1 N1 Ru1 125.45(17) . . ? C2 N1 Ru1 128.51(15) . . ? C1 N2 C7 106.98(19) . . ? C1 N2 C8 127.7(2) . . ? C7 N2 C8 125.3(2) . . ? N1 C1 N2 112.8(2) . . ? N1 C1 H1 123.6 . . ? N2 C1 H1 123.6 . . ? C3 C2 C7 120.3(2) . . ? C3 C2 N1 131.3(2) . . ? C7 C2 N1 108.4(2) . . ? C4 C3 C2 117.5(3) . . ? C4 C3 H3 121.2 . . ? C2 C3 H3 121.2 . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 122.3(3) . . ? C6 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? C5 C6 C7 116.3(3) . . ? C5 C6 H6 121.8 . . ? C7 C6 H6 121.8 . . ? N2 C7 C6 132.1(2) . . ? N2 C7 C2 105.8(2) . . ? C6 C7 C2 122.1(2) . . ? N2 C8 C9 111.3(2) . . ? N2 C8 C15 110.5(2) . . ? C9 C8 C15 114.6(2) . . ? N2 C8 H8 106.6 . . ? C9 C8 H8 106.6 . . ? C15 C8 H8 106.6 . . ? C10 C9 C14 118.6(3) . . ? C10 C9 C8 121.7(2) . . ? C14 C9 C8 119.7(3) . . ? C11 C10 C9 120.9(3) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C12 C11 C10 120.0(3) . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C13 C12 C11 120.0(3) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C14 120.6(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C9 C14 C13 119.9(3) . . ? C9 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C16 C15 C20 118.2(2) . . ? C16 C15 C8 123.1(2) . . ? C20 C15 C8 118.6(2) . . ? C17 C16 C15 120.2(3) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.6(3) . . ? C18 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? C17 C18 C19 119.6(3) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C18 C19 C20 120.0(3) . . ? C18 C19 H19 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 C15 121.3(3) . . ? C19 C20 H20 119.3 . . ? C15 C20 H20 119.3 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C27 C22 C23 118.3(2) . . ? C27 C22 C21 122.0(3) . . ? C23 C22 C21 119.6(3) . . ? C27 C22 Ru1 69.77(14) . . ? C23 C22 Ru1 70.11(14) . . ? C21 C22 Ru1 130.0(2) . . ? C24 C23 C22 120.5(2) . . ? C24 C23 Ru1 70.11(15) . . ? C22 C23 Ru1 72.14(15) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? Ru1 C23 H23 130.6 . . ? C23 C24 C25 122.4(3) . . ? C23 C24 Ru1 72.50(16) . . ? C25 C24 Ru1 72.03(15) . . ? C23 C24 H24 118.8 . . ? C25 C24 H24 118.8 . . ? Ru1 C24 H24 129.3 . . ? C26 C25 C24 116.3(3) . . ? C26 C25 C28 123.4(3) . . ? C24 C25 C28 120.2(3) . . ? C26 C25 Ru1 69.22(15) . . ? C24 C25 Ru1 69.77(15) . . ? C28 C25 Ru1 129.7(2) . . ? C27 C26 C25 122.1(3) . . ? C27 C26 Ru1 72.12(14) . . ? C25 C26 Ru1 72.60(14) . . ? C27 C26 H26 118.9 . . ? C25 C26 H26 118.9 . . ? Ru1 C26 H26 128.8 . . ? C22 C27 C26 120.3(2) . . ? C22 C27 Ru1 72.81(14) . . ? C26 C27 Ru1 69.65(14) . . ? C22 C27 H27 119.8 . . ? C26 C27 H27 119.8 . . ? Ru1 C27 H27 130.3 . . ? C29 C28 C25 113.7(3) . . ? C29 C28 C30 111.4(3) . . ? C25 C28 C30 109.3(3) . . ? C29 C28 H28 107.4 . . ? C25 C28 H28 107.4 . . ? C30 C28 H28 107.4 . . ? C28 C29 H29A 109.5 . . ? C28 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C28 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C28 C30 H30A 109.5 . . ? C28 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C28 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 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 2.130(2) . ? Ru1 C26 2.149(2) . ? Ru1 C24 2.163(3) . ? Ru1 C27 2.181(2) . ? Ru1 C25 2.193(3) . ? Ru1 C23 2.194(3) . ? Ru1 C22 2.221(3) . ? Ru1 Cl1 2.4112(7) . ? Ru1 Cl2 2.4335(7) . ? N1 C1 1.317(3) . ? N1 C2 1.403(3) . ? N2 C1 1.353(3) . ? N2 C7 1.395(3) . ? N2 C8 1.477(3) . ? C1 H1 0.9300 . ? C2 C3 1.400(3) . ? C2 C7 1.402(3) . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C4 C5 1.394(5) . ? C4 H4 0.9300 . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 C7 1.396(4) . ? C6 H6 0.9300 . ? C8 C9 1.523(4) . ? C8 C15 1.529(3) . ? C8 H8 0.9800 . ? C9 C10 1.392(4) . ? C9 C14 1.392(4) . ? C10 C11 1.382(4) . ? C10 H10 0.9300 . ? C11 C12 1.382(5) . ? C11 H11 0.9300 . ? C12 C13 1.365(6) . ? C12 H12 0.9300 . ? C13 C14 1.397(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? C15 C16 1.389(4) . ? C15 C20 1.390(4) . ? C16 C17 1.389(4) . ? C16 H16 0.9300 . ? C17 C18 1.373(4) . ? C17 H17 0.9300 . ? C18 C19 1.376(4) . ? C18 H18 0.9300 . ? C19 C20 1.377(4) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.491(4) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C27 1.412(4) . ? C22 C23 1.428(4) . ? C23 C24 1.397(4) . ? C23 H23 0.9300 . ? C24 C25 1.426(4) . ? C24 H24 0.9300 . ? C25 C26 1.420(4) . ? C25 C28 1.524(4) . ? C26 C27 1.418(4) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 C29 1.508(5) . ? C28 C30 1.530(5) . ? C28 H28 0.9800 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 -0.7(3) . . . . ? Ru1 N1 C1 N2 176.16(16) . . . . ? C7 N2 C1 N1 0.0(3) . . . . ? C8 N2 C1 N1 -179.5(2) . . . . ? C1 N1 C2 C3 -178.4(3) . . . . ? Ru1 N1 C2 C3 4.9(4) . . . . ? C1 N1 C2 C7 1.2(3) . . . . ? Ru1 N1 C2 C7 -175.58(16) . . . . ? C7 C2 C3 C4 -0.1(4) . . . . ? N1 C2 C3 C4 179.4(3) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? C3 C4 C5 C6 0.0(5) . . . . ? C4 C5 C6 C7 -1.2(5) . . . . ? C1 N2 C7 C6 -179.8(3) . . . . ? C8 N2 C7 C6 -0.3(4) . . . . ? C1 N2 C7 C2 0.7(3) . . . . ? C8 N2 C7 C2 -179.8(2) . . . . ? C5 C6 C7 N2 -177.7(3) . . . . ? C5 C6 C7 C2 1.7(4) . . . . ? C3 C2 C7 N2 178.5(2) . . . . ? N1 C2 C7 N2 -1.2(3) . . . . ? C3 C2 C7 C6 -1.1(4) . . . . ? N1 C2 C7 C6 179.3(2) . . . . ? C1 N2 C8 C9 92.5(3) . . . . ? C7 N2 C8 C9 -86.9(3) . . . . ? C1 N2 C8 C15 -36.1(3) . . . . ? C7 N2 C8 C15 144.5(2) . . . . ? N2 C8 C9 C10 -48.4(3) . . . . ? C15 C8 C9 C10 77.9(3) . . . . ? N2 C8 C9 C14 132.7(3) . . . . ? C15 C8 C9 C14 -101.0(3) . . . . ? C14 C9 C10 C11 0.6(4) . . . . ? C8 C9 C10 C11 -178.4(3) . . . . ? C9 C10 C11 C12 -1.1(5) . . . . ? C10 C11 C12 C13 1.5(5) . . . . ? C11 C12 C13 C14 -1.4(5) . . . . ? C10 C9 C14 C13 -0.5(4) . . . . ? C8 C9 C14 C13 178.5(3) . . . . ? C12 C13 C14 C9 1.0(5) . . . . ? N2 C8 C15 C16 128.8(3) . . . . ? C9 C8 C15 C16 2.1(3) . . . . ? N2 C8 C15 C20 -54.5(3) . . . . ? C9 C8 C15 C20 178.8(2) . . . . ? C20 C15 C16 C17 -0.5(4) . . . . ? C8 C15 C16 C17 176.2(3) . . . . ? C15 C16 C17 C18 0.7(5) . . . . ? C16 C17 C18 C19 -0.2(5) . . . . ? C17 C18 C19 C20 -0.6(5) . . . . ? C18 C19 C20 C15 0.8(5) . . . . ? C16 C15 C20 C19 -0.3(4) . . . . ? C8 C15 C20 C19 -177.1(3) . . . . ? C27 C22 C23 C24 0.7(4) . . . . ? C21 C22 C23 C24 178.4(3) . . . . ? Ru1 C22 C23 C24 52.8(2) . . . . ? C27 C22 C23 Ru1 -52.2(2) . . . . ? C21 C22 C23 Ru1 125.5(3) . . . . ? C22 C23 C24 C25 0.5(4) . . . . ? Ru1 C23 C24 C25 54.3(2) . . . . ? C22 C23 C24 Ru1 -53.8(2) . . . . ? C23 C24 C25 C26 -1.6(4) . . . . ? Ru1 C24 C25 C26 52.8(2) . . . . ? C23 C24 C25 C28 -179.5(3) . . . . ? Ru1 C24 C25 C28 -125.0(3) . . . . ? C23 C24 C25 Ru1 -54.5(2) . . . . ? C24 C25 C26 C27 1.7(4) . . . . ? C28 C25 C26 C27 179.4(3) . . . . ? Ru1 C25 C26 C27 54.8(2) . . . . ? C24 C25 C26 Ru1 -53.1(2) . . . . ? C28 C25 C26 Ru1 124.6(3) . . . . ? C23 C22 C27 C26 -0.6(4) . . . . ? C21 C22 C27 C26 -178.3(3) . . . . ? Ru1 C22 C27 C26 -53.0(2) . . . . ? C23 C22 C27 Ru1 52.4(2) . . . . ? C21 C22 C27 Ru1 -125.3(3) . . . . ? C25 C26 C27 C22 -0.6(4) . . . . ? Ru1 C26 C27 C22 54.4(2) . . . . ? C25 C26 C27 Ru1 -55.0(2) . . . . ? C26 C25 C28 C29 -36.3(4) . . . . ? C24 C25 C28 C29 141.3(3) . . . . ? Ru1 C25 C28 C29 53.4(4) . . . . ? C26 C25 C28 C30 88.8(4) . . . . ? C24 C25 C28 C30 -93.6(3) . . . . ? Ru1 C25 C28 C30 178.5(2) . . . . ?