#------------------------------------------------------------------------------ #$Date: 2021-11-06 00:51:34 +0200 (Sat, 06 Nov 2021) $ #$Revision: 270327 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061046.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_7061046 loop_ _publ_author_name 'Sato, Hiroki' 'Tsukamoto, Tadashi' 'Sogawa, Hiromitsu' 'Kuwata, Shigeki' 'Takata, Toshikazu' _publ_section_title ; Ruthenium macrocycles bearing pyridine bis(carboxamide): synthesis, structure, and catalytic activity for hydrosilylation ; _journal_issue 39 _journal_name_full 'New Journal of Chemistry' _journal_page_first 18282 _journal_page_last 18289 _journal_paper_doi 10.1039/D0NJ06133F _journal_volume 45 _journal_year 2021 _chemical_formula_moiety 'C25 H23 N3 O7 Ru, C3 H7 N O' _chemical_formula_sum 'C28 H30 N4 O8 Ru' _chemical_formula_weight 651.64 _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_update_record ; 2020-02-01 deposited with the CCDC. 2021-08-30 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 102.617(3) _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 10.696(2) _cell_length_b 22.632(5) _cell_length_c 11.846(3) _cell_measurement_reflns_used 8994 _cell_measurement_temperature 93 _cell_measurement_theta_max 27.45 _cell_measurement_theta_min 3.04 _cell_volume 2798.3(11) _computing_cell_refinement CrystalClear _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction CrystalClear _computing_molecular_graphics 'CrystalStructure 4.3' _computing_publication_material 'CrystalStructure 4.3 (Rigaku, 2018)' _computing_structure_refinement 'SHELXL Version 2014/7 (Sheldrick, 2008)' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _diffrn_ambient_temperature 93 _diffrn_detector_area_resol_mean 7.111 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_unetI/netI 0.0549 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 22752 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.422 _diffrn_reflns_theta_min 3.038 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.617 _exptl_absorpt_correction_T_max 0.934 _exptl_absorpt_correction_T_min 0.785 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.547 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1336.00 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dimethylformamide/water' _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.110 _refine_diff_density_max 1.64 _refine_diff_density_min -0.45 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment mixed _refine_ls_number_parameters 380 _refine_ls_number_reflns 6369 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0344 _refine_ls_shift/su_max 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0444P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.0905 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4965 _reflns_number_total 6369 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file d0nj06133f2.cif _cod_data_source_block RuACCO2MeCN _cod_original_cell_volume 2798.4(10) _cod_database_code 7061046 _shelx_res_file ; shelxl.res created by SHELXL-2014/7 TITL Takata151209 CELL 0.71075 10.69630 22.63200 11.84600 90.00000 102.61710 90.00000 ZERR 4 0.00230 0.00480 0.00260 0.00000 0.00340 0.00000 LATT 1 SYMM -X, .50+Y, .50-Z SFAC C H N O RU UNIT 112 120 16 32 4 L.S. 5 FMAP 2 PLAN 25 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -179.8 ACTA SIZE 0.150 0.150 0.110 WGHT 0.044400 FVAR 0.28403 RU1 5 0.232729 0.398956 0.429697 11.00000 0.00928 0.01016 = 0.01293 -0.00190 0.00008 -0.00055 O1 4 0.009345 0.458153 0.657018 11.00000 0.01106 0.02017 = 0.01761 0.00300 0.00390 0.00302 O2 4 0.624484 0.432952 0.535561 11.00000 0.01013 0.01486 = 0.01962 -0.00120 0.00105 0.00008 O3 4 -0.162448 0.159605 0.372080 11.00000 0.02110 0.01369 = 0.02163 -0.00253 0.00049 -0.00284 O4 4 0.550996 0.127194 0.396210 11.00000 0.03068 0.01098 = 0.02471 -0.00091 0.00378 -0.00214 O5 4 0.254896 0.274904 0.521089 11.00000 0.02144 0.01438 = 0.03267 0.00320 0.00019 -0.00029 O6 4 0.124602 0.348796 0.189508 11.00000 0.03315 0.03921 = 0.01829 -0.00997 0.00092 -0.01123 O7 4 0.214433 0.486887 0.360380 11.00000 0.00921 0.01366 = 0.01900 0.00044 0.00092 0.00043 AFIX 2 H1 2 0.144967 0.501682 0.360465 11.00000 -1.50000 H2 2 0.270981 0.507666 0.391280 11.00000 -1.50000 AFIX 0 O8 4 0.335106 0.050006 0.570958 11.00000 0.02764 0.04825 = 0.03355 0.00773 -0.00255 0.00961 N1 3 0.309070 0.437569 0.583416 11.00000 0.01024 0.00867 = 0.01247 0.00116 0.00295 0.00005 N2 3 0.068313 0.417780 0.494745 11.00000 0.00912 0.01230 = 0.01765 0.00043 0.00209 -0.00139 N3 3 0.427996 0.403346 0.426419 11.00000 0.01166 0.01095 = 0.01357 -0.00089 0.00269 0.00094 N4 3 0.180915 0.101656 0.446257 11.00000 0.01874 0.02639 = 0.02249 -0.00300 0.00215 0.00060 C1 1 0.229624 0.455279 0.649839 11.00000 0.01182 0.00909 = 0.01477 0.00317 0.00315 -0.00021 C2 1 0.278665 0.483974 0.753938 11.00000 0.01517 0.01244 = 0.01409 0.00164 0.00541 0.00126 AFIX 43 H3 2 0.223719 0.496891 0.802079 11.00000 -1.20000 AFIX 0 C3 1 0.410017 0.493252 0.785679 11.00000 0.01667 0.01177 = 0.01285 -0.00029 -0.00001 -0.00006 AFIX 43 H4 2 0.445828 0.511484 0.857722 11.00000 -1.20000 AFIX 0 C4 1 0.489935 0.476102 0.712971 11.00000 0.01138 0.01083 = 0.01619 0.00206 0.00022 0.00007 AFIX 43 H5 2 0.579458 0.483485 0.733766 11.00000 -1.20000 AFIX 0 C5 1 0.436250 0.448129 0.609986 11.00000 0.01203 0.00735 = 0.01481 0.00236 0.00169 -0.00068 C6 1 0.089715 0.443222 0.598842 11.00000 0.01161 0.00925 = 0.01695 0.00437 0.00093 0.00179 C7 1 0.504377 0.427149 0.518767 11.00000 0.01235 0.00748 = 0.01605 0.00229 0.00291 0.00143 C8 1 -0.064852 0.405600 0.435630 11.00000 0.00922 0.01492 = 0.02020 0.00088 -0.00122 0.00028 AFIX 23 H6 2 -0.083865 0.426418 0.360314 11.00000 -1.20000 H7 2 -0.123080 0.421388 0.482815 11.00000 -1.20000 AFIX 0 C9 1 -0.090603 0.340368 0.415334 11.00000 0.00618 0.01499 = 0.01778 0.00018 0.00262 0.00002 C10 1 -0.060564 0.300109 0.506499 11.00000 0.01331 0.01898 = 0.01216 -0.00127 0.00093 -0.00184 AFIX 43 H8 2 -0.021961 0.313994 0.581719 11.00000 -1.20000 AFIX 0 C11 1 -0.085699 0.240653 0.489744 11.00000 0.01278 0.01836 = 0.01502 0.00419 0.00089 -0.00094 AFIX 43 H9 2 -0.064658 0.214053 0.553098 11.00000 -1.20000 AFIX 0 C12 1 -0.142314 0.219410 0.379221 11.00000 0.00994 0.01392 = 0.01875 -0.00237 0.00296 -0.00126 C13 1 -0.172782 0.258484 0.287441 11.00000 0.01622 0.02198 = 0.01354 -0.00251 -0.00143 -0.00247 AFIX 43 H10 2 -0.211201 0.244619 0.212161 11.00000 -1.20000 AFIX 0 C14 1 -0.146374 0.318595 0.306780 11.00000 0.01566 0.01857 = 0.01572 0.00370 0.00028 -0.00114 AFIX 43 H11 2 -0.167314 0.345289 0.243573 11.00000 -1.20000 AFIX 0 C15 1 -0.216950 0.134641 0.261446 11.00000 0.02370 0.01822 = 0.02498 -0.00780 0.00443 -0.00466 AFIX 137 H12 2 -0.225954 0.091830 0.269228 11.00000 -1.50000 H13 2 -0.160872 0.142786 0.208007 11.00000 -1.50000 H14 2 -0.301395 0.152189 0.231246 11.00000 -1.50000 AFIX 0 C16 1 0.489493 0.376068 0.338843 11.00000 0.01466 0.01485 = 0.01312 -0.00107 0.00353 0.00075 AFIX 23 H15 2 0.575160 0.393865 0.344320 11.00000 -1.20000 H16 2 0.437301 0.384370 0.260594 11.00000 -1.20000 AFIX 0 C17 1 0.503390 0.309813 0.355886 11.00000 0.01079 0.01408 = 0.01664 -0.00249 0.00523 -0.00009 C18 1 0.567045 0.286959 0.461819 11.00000 0.01978 0.01669 = 0.01632 -0.00518 0.00058 0.00131 AFIX 43 H17 2 0.600067 0.313315 0.523553 11.00000 -1.20000 AFIX 0 C19 1 0.583623 0.226276 0.479698 11.00000 0.01976 0.01605 = 0.01375 0.00148 0.00126 0.00209 AFIX 43 H18 2 0.626010 0.211458 0.553135 11.00000 -1.20000 AFIX 0 C20 1 0.537712 0.188026 0.389431 11.00000 0.01693 0.01307 = 0.02173 -0.00075 0.00628 -0.00111 C21 1 0.472047 0.209854 0.283473 11.00000 0.02517 0.01821 = 0.01889 -0.00594 0.00068 -0.00255 AFIX 43 H19 2 0.438768 0.183399 0.221983 11.00000 -1.20000 AFIX 0 C22 1 0.454983 0.270376 0.267325 11.00000 0.02162 0.01839 = 0.01421 -0.00101 0.00139 0.00005 AFIX 43 H20 2 0.409578 0.284970 0.194705 11.00000 -1.20000 AFIX 0 C23 1 0.629670 0.103507 0.499549 11.00000 0.02811 0.01643 = 0.02642 0.00543 0.00737 0.00187 AFIX 137 H21 2 0.590131 0.111642 0.565158 11.00000 -1.50000 H22 2 0.714571 0.121925 0.513272 11.00000 -1.50000 H23 2 0.638234 0.060717 0.491051 11.00000 -1.50000 AFIX 0 C24 1 0.246666 0.322335 0.486453 11.00000 0.01042 0.02023 = 0.01664 -0.00335 0.00095 -0.00208 C25 1 0.163326 0.367758 0.279912 11.00000 0.01491 0.01886 = 0.02281 -0.00049 0.00470 -0.00119 C26 1 0.300413 0.091697 0.505240 11.00000 0.02086 0.03918 = 0.02659 -0.00747 0.00186 0.00359 AFIX 43 H24 2 0.364181 0.119279 0.495516 11.00000 -1.20000 AFIX 0 C27 1 0.077333 0.062433 0.458816 11.00000 0.02222 0.03026 = 0.03255 0.00033 0.00429 0.00028 AFIX 137 H25 2 0.011715 0.085009 0.486378 11.00000 -1.50000 H26 2 0.110934 0.031297 0.514727 11.00000 -1.50000 H27 2 0.039463 0.044528 0.383816 11.00000 -1.50000 AFIX 0 C28 1 0.151986 0.151291 0.367930 11.00000 0.02500 0.02672 = 0.03432 -0.00334 0.00617 0.00290 AFIX 137 H28 2 0.231998 0.169855 0.358902 11.00000 -1.50000 H29 2 0.100388 0.180169 0.399380 11.00000 -1.50000 H30 2 0.103977 0.137469 0.292452 11.00000 -1.50000 AFIX 0 HKLF 4 REM Takata151209 REM R1 = 0.0344 for 4965 Fo > 4sig(Fo) and 0.0431 for all 6369 data REM 380 parameters refined using 0 restraints END WGHT 0.0444 0.0000 REM Instructions for potential hydrogen bonds EQIV $1 -x, -y+1, -z+1 HTAB O7 O1_$1 EQIV $2 -x+1, -y+1, -z+1 HTAB O7 O2_$2 EQIV $3 x+1, y, z HTAB C23 O3_$3 EQIV $4 -x+1, -y, -z+1 HTAB C23 O8_$4 HTAB C26 O4 HTAB C27 O3 EQIV $5 x, -y+1/2, z-1/2 HTAB C27 O1_$5 REM Highest difference peak 1.636, deepest hole -0.453, 1-sigma level 0.143 Q1 1 0.7709 0.1966 0.5714 11.00000 0.05 1.22 Q2 1 0.2951 0.3990 0.7089 11.00000 0.05 0.93 Q3 1 0.2330 0.3722 0.4990 11.00000 0.05 0.90 Q4 1 0.1731 0.3711 0.4212 11.00000 0.05 0.85 Q5 1 0.2327 0.3714 0.3607 11.00000 0.05 0.83 Q6 1 0.2142 0.4092 0.3502 11.00000 0.05 0.82 Q7 1 0.2416 0.3504 0.4178 11.00000 0.05 0.78 Q8 1 0.2927 0.3688 0.4398 11.00000 0.05 0.77 Q9 1 0.1700 0.4207 0.3979 11.00000 0.05 0.75 Q10 1 0.4568 0.4368 0.5614 11.00000 0.05 0.72 Q11 1 0.1132 0.4020 0.4507 11.00000 0.05 0.71 Q12 1 0.2536 0.4250 0.5146 11.00000 0.05 0.70 Q13 1 0.3567 0.4001 0.4100 11.00000 0.05 0.62 Q14 1 -0.1027 0.2339 0.4189 11.00000 0.05 0.61 Q15 1 0.1592 0.4486 0.6264 11.00000 0.05 0.57 Q16 1 -0.0895 0.3288 0.3610 11.00000 0.05 0.54 Q17 1 0.2290 0.4514 0.4253 11.00000 0.05 0.54 Q18 1 0.5510 0.1701 0.3873 11.00000 0.05 0.54 Q19 1 0.5042 0.2896 0.3042 11.00000 0.05 0.53 Q20 1 0.3325 0.4939 0.7681 11.00000 0.05 0.53 Q21 1 0.4498 0.3942 0.3983 11.00000 0.05 0.53 Q22 1 0.5653 0.4409 0.5226 11.00000 0.05 0.52 Q23 1 -0.1493 0.2415 0.3373 11.00000 0.05 0.51 Q24 1 0.0879 0.4366 0.5314 11.00000 0.05 0.51 Q25 1 0.0474 0.4378 0.6410 11.00000 0.05 0.50 ; _shelx_res_checksum 71986 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 -X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 +X,-1/2-Y,-1/2+Z 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 0.23273(2) 0.39896(2) 0.42970(2) 0.01115(7) Uani 1 1 d . . . . . O1 O 0.00935(15) 0.45815(7) 0.65702(15) 0.0162(4) Uani 1 1 d . . . . . O2 O 0.62448(15) 0.43295(7) 0.53556(15) 0.0152(4) Uani 1 1 d . . . . . O3 O -0.16245(17) 0.15960(7) 0.37208(15) 0.0194(4) Uani 1 1 d . . . . . O4 O 0.55100(18) 0.12719(8) 0.39621(16) 0.0225(4) Uani 1 1 d . . . . . O5 O 0.25490(17) 0.27490(8) 0.52109(17) 0.0237(4) Uani 1 1 d . . . . . O6 O 0.12460(19) 0.34880(9) 0.18951(16) 0.0309(5) Uani 1 1 d . . . . . O7 O 0.21443(17) 0.48689(8) 0.36038(15) 0.0143(4) Uani 1 1 d . . . . . H1 H 0.145(3) 0.5017(12) 0.360(2) 0.021 Uiso 1 1 d . U . . . H2 H 0.271(3) 0.5077(13) 0.391(3) 0.021 Uiso 1 1 d . U . . . O8 O 0.3351(2) 0.05001(10) 0.57096(18) 0.0379(5) Uani 1 1 d . . . . . N1 N 0.30907(18) 0.43757(8) 0.58342(16) 0.0104(4) Uani 1 1 d . . . . . N2 N 0.06831(18) 0.41778(9) 0.49474(18) 0.0131(4) Uani 1 1 d . . . . . N3 N 0.42800(19) 0.40335(8) 0.42642(17) 0.0121(4) Uani 1 1 d . . . . . N4 N 0.1809(2) 0.10166(10) 0.4463(2) 0.0229(5) Uani 1 1 d . . . . . C1 C 0.2296(2) 0.45528(10) 0.6498(2) 0.0119(5) Uani 1 1 d . . . . . C2 C 0.2787(2) 0.48397(10) 0.7539(2) 0.0136(5) Uani 1 1 d . . . . . H3 H 0.2237 0.4969 0.8021 0.016 Uiso 1 1 calc R U . . . C3 C 0.4100(2) 0.49325(10) 0.7857(2) 0.0143(5) Uani 1 1 d . . . . . H4 H 0.4458 0.5115 0.8577 0.017 Uiso 1 1 calc R U . . . C4 C 0.4899(2) 0.47610(10) 0.7130(2) 0.0132(5) Uani 1 1 d . . . . . H5 H 0.5795 0.4835 0.7338 0.016 Uiso 1 1 calc R U . . . C5 C 0.4363(2) 0.44813(10) 0.6100(2) 0.0116(5) Uani 1 1 d . . . . . C6 C 0.0897(2) 0.44322(10) 0.5988(2) 0.0129(5) Uani 1 1 d . . . . . C7 C 0.5044(2) 0.42715(10) 0.5188(2) 0.0120(5) Uani 1 1 d . . . . . C8 C -0.0649(2) 0.40560(10) 0.4356(2) 0.0155(5) Uani 1 1 d . . . . . H6 H -0.0839 0.4264 0.3603 0.019 Uiso 1 1 calc R U . . . H7 H -0.1231 0.4214 0.4828 0.019 Uiso 1 1 calc R U . . . C9 C -0.0906(2) 0.34037(11) 0.4153(2) 0.0130(5) Uani 1 1 d . . . . . C10 C -0.0606(2) 0.30011(11) 0.5065(2) 0.0151(5) Uani 1 1 d . . . . . H8 H -0.0220 0.3140 0.5817 0.018 Uiso 1 1 calc R U . . . C11 C -0.0857(2) 0.24065(11) 0.4897(2) 0.0157(5) Uani 1 1 d . . . . . H9 H -0.0647 0.2141 0.5531 0.019 Uiso 1 1 calc R U . . . C12 C -0.1423(2) 0.21941(11) 0.3792(2) 0.0142(5) Uani 1 1 d . . . . . C13 C -0.1728(2) 0.25848(11) 0.2874(2) 0.0180(5) Uani 1 1 d . . . . . H10 H -0.2112 0.2446 0.2122 0.022 Uiso 1 1 calc R U . . . C14 C -0.1464(2) 0.31860(11) 0.3068(2) 0.0171(5) Uani 1 1 d . . . . . H11 H -0.1673 0.3453 0.2436 0.021 Uiso 1 1 calc R U . . . C15 C -0.2170(3) 0.13464(12) 0.2614(2) 0.0224(6) Uani 1 1 d . . . . . H12 H -0.2260 0.0918 0.2692 0.034 Uiso 1 1 calc R U . . . H13 H -0.1609 0.1428 0.2080 0.034 Uiso 1 1 calc R U . . . H14 H -0.3014 0.1522 0.2312 0.034 Uiso 1 1 calc R U . . . C16 C 0.4895(2) 0.37607(10) 0.3388(2) 0.0141(5) Uani 1 1 d . . . . . H15 H 0.5752 0.3939 0.3443 0.017 Uiso 1 1 calc R U . . . H16 H 0.4373 0.3844 0.2606 0.017 Uiso 1 1 calc R U . . . C17 C 0.5034(2) 0.30981(10) 0.3559(2) 0.0135(5) Uani 1 1 d . . . . . C18 C 0.5670(2) 0.28696(11) 0.4618(2) 0.0181(5) Uani 1 1 d . . . . . H17 H 0.6001 0.3133 0.5236 0.022 Uiso 1 1 calc R U . . . C19 C 0.5836(2) 0.22628(11) 0.4797(2) 0.0169(5) Uani 1 1 d . . . . . H18 H 0.6260 0.2115 0.5531 0.020 Uiso 1 1 calc R U . . . C20 C 0.5377(2) 0.18803(11) 0.3894(2) 0.0169(5) Uani 1 1 d . . . . . C21 C 0.4720(3) 0.20985(11) 0.2835(2) 0.0214(6) Uani 1 1 d . . . . . H19 H 0.4388 0.1834 0.2220 0.026 Uiso 1 1 calc R U . . . C22 C 0.4550(2) 0.27038(11) 0.2673(2) 0.0185(5) Uani 1 1 d . . . . . H20 H 0.4096 0.2850 0.1947 0.022 Uiso 1 1 calc R U . . . C23 C 0.6297(3) 0.10351(11) 0.4995(2) 0.0234(6) Uani 1 1 d . . . . . H21 H 0.5901 0.1116 0.5652 0.035 Uiso 1 1 calc R U . . . H22 H 0.7146 0.1219 0.5133 0.035 Uiso 1 1 calc R U . . . H23 H 0.6382 0.0607 0.4911 0.035 Uiso 1 1 calc R U . . . C24 C 0.2467(2) 0.32234(11) 0.4865(2) 0.0161(5) Uani 1 1 d . . . . . C25 C 0.1633(2) 0.36776(11) 0.2799(2) 0.0188(5) Uani 1 1 d . . . . . C26 C 0.3004(3) 0.09170(14) 0.5052(3) 0.0294(7) Uani 1 1 d . . . . . H24 H 0.3642 0.1193 0.4955 0.035 Uiso 1 1 calc R U . . . C27 C 0.0773(3) 0.06243(13) 0.4588(3) 0.0286(7) Uani 1 1 d . . . . . H25 H 0.0117 0.0850 0.4864 0.043 Uiso 1 1 calc R U . . . H26 H 0.1109 0.0313 0.5147 0.043 Uiso 1 1 calc R U . . . H27 H 0.0395 0.0445 0.3838 0.043 Uiso 1 1 calc R U . . . C28 C 0.1520(3) 0.15129(12) 0.3679(3) 0.0287(7) Uani 1 1 d . . . . . H28 H 0.2320 0.1699 0.3589 0.043 Uiso 1 1 calc R U . . . H29 H 0.1004 0.1802 0.3994 0.043 Uiso 1 1 calc R U . . . H30 H 0.1040 0.1375 0.2925 0.043 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 0.00928(11) 0.01016(11) 0.01293(11) -0.00190(7) 0.00008(7) -0.00055(7) O1 0.0111(8) 0.0202(9) 0.0176(9) 0.0030(7) 0.0039(7) 0.0030(7) O2 0.0101(8) 0.0149(9) 0.0196(9) -0.0012(7) 0.0010(7) 0.0001(7) O3 0.0211(9) 0.0137(9) 0.0216(10) -0.0025(7) 0.0005(8) -0.0028(7) O4 0.0307(11) 0.0110(9) 0.0247(10) -0.0009(8) 0.0038(8) -0.0021(8) O5 0.0214(10) 0.0144(9) 0.0327(11) 0.0032(8) 0.0002(8) -0.0003(8) O6 0.0332(12) 0.0392(12) 0.0183(10) -0.0100(9) 0.0009(9) -0.0112(10) O7 0.0092(9) 0.0137(9) 0.0190(10) 0.0004(7) 0.0009(7) 0.0004(7) O8 0.0276(12) 0.0482(14) 0.0335(12) 0.0077(11) -0.0025(10) 0.0096(10) N1 0.0102(9) 0.0087(9) 0.0125(10) 0.0012(8) 0.0030(8) 0.0001(8) N2 0.0091(10) 0.0123(10) 0.0176(11) 0.0004(8) 0.0021(8) -0.0014(8) N3 0.0117(10) 0.0110(10) 0.0136(10) -0.0009(8) 0.0027(8) 0.0009(8) N4 0.0187(12) 0.0264(13) 0.0225(12) -0.0030(10) 0.0022(10) 0.0006(10) C1 0.0118(11) 0.0091(10) 0.0148(12) 0.0032(9) 0.0032(9) -0.0002(9) C2 0.0152(12) 0.0124(11) 0.0141(12) 0.0016(9) 0.0054(10) 0.0013(10) C3 0.0167(12) 0.0118(11) 0.0129(12) -0.0003(9) 0.0000(10) -0.0001(10) C4 0.0114(11) 0.0108(11) 0.0162(12) 0.0021(9) 0.0002(9) 0.0001(9) C5 0.0120(11) 0.0073(11) 0.0148(12) 0.0024(9) 0.0017(9) -0.0007(9) C6 0.0116(12) 0.0093(11) 0.0169(12) 0.0044(9) 0.0009(10) 0.0018(9) C7 0.0124(12) 0.0075(10) 0.0160(12) 0.0023(9) 0.0029(9) 0.0014(9) C8 0.0092(12) 0.0149(12) 0.0202(13) 0.0009(10) -0.0012(10) 0.0003(9) C9 0.0062(11) 0.0150(12) 0.0178(13) 0.0002(10) 0.0026(9) 0.0000(9) C10 0.0133(12) 0.0190(12) 0.0122(12) -0.0013(10) 0.0009(10) -0.0018(10) C11 0.0128(12) 0.0184(12) 0.0150(12) 0.0042(10) 0.0009(10) -0.0009(10) C12 0.0099(11) 0.0139(11) 0.0187(13) -0.0024(10) 0.0030(10) -0.0013(10) C13 0.0162(13) 0.0220(13) 0.0135(12) -0.0025(10) -0.0014(10) -0.0025(11) C14 0.0157(12) 0.0186(13) 0.0157(13) 0.0037(10) 0.0003(10) -0.0011(10) C15 0.0237(14) 0.0182(13) 0.0250(15) -0.0078(11) 0.0044(11) -0.0047(11) C16 0.0147(12) 0.0148(12) 0.0131(12) -0.0011(10) 0.0035(10) 0.0007(10) C17 0.0108(11) 0.0141(12) 0.0166(12) -0.0025(10) 0.0052(10) -0.0001(10) C18 0.0198(13) 0.0167(12) 0.0163(13) -0.0052(10) 0.0006(10) 0.0013(11) C19 0.0198(13) 0.0160(12) 0.0138(12) 0.0015(10) 0.0013(10) 0.0021(10) C20 0.0169(13) 0.0131(12) 0.0217(13) -0.0007(10) 0.0063(11) -0.0011(10) C21 0.0252(14) 0.0182(13) 0.0189(13) -0.0059(11) 0.0007(11) -0.0026(11) C22 0.0216(13) 0.0184(13) 0.0142(12) -0.0010(10) 0.0014(10) 0.0000(11) C23 0.0281(16) 0.0164(13) 0.0264(15) 0.0054(11) 0.0074(12) 0.0019(11) C24 0.0104(12) 0.0202(13) 0.0166(13) -0.0034(11) 0.0009(10) -0.0021(10) C25 0.0149(13) 0.0189(13) 0.0228(14) -0.0005(11) 0.0047(11) -0.0012(11) C26 0.0209(15) 0.0392(18) 0.0266(16) -0.0075(13) 0.0019(12) 0.0036(13) C27 0.0222(15) 0.0303(16) 0.0326(17) 0.0003(13) 0.0043(13) 0.0003(13) C28 0.0250(15) 0.0267(15) 0.0343(17) -0.0033(13) 0.0062(13) 0.0029(13) 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 for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; N N 0.0061 0.0033 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0106 0.0060 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Ru Ru -1.2594 0.8363 ; International Tables for Crystallography (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 C24 Ru1 C25 88.58(11) . . ? C24 Ru1 N1 95.33(9) . . ? C25 Ru1 N1 175.90(9) . . ? C24 Ru1 N3 92.83(9) . . ? C25 Ru1 N3 100.80(9) . . ? N1 Ru1 N3 77.80(8) . . ? C24 Ru1 N2 93.66(9) . . ? C25 Ru1 N2 103.22(9) . . ? N1 Ru1 N2 77.83(8) . . ? N3 Ru1 N2 155.25(8) . . ? C24 Ru1 O7 178.74(9) . . ? C25 Ru1 O7 90.17(9) . . ? N1 Ru1 O7 85.93(7) . . ? N3 Ru1 O7 87.53(7) . . ? N2 Ru1 O7 86.50(7) . . ? C12 O3 C15 118.3(2) . . ? C20 O4 C23 117.1(2) . . ? Ru1 O7 H1 113(2) . . ? Ru1 O7 H2 112(2) . . ? H1 O7 H2 111(3) . . ? C1 N1 C5 123.1(2) . . ? C1 N1 Ru1 118.34(16) . . ? C5 N1 Ru1 118.33(15) . . ? C6 N2 C8 118.3(2) . . ? C6 N2 Ru1 115.83(16) . . ? C8 N2 Ru1 125.87(16) . . ? C7 N3 C16 117.3(2) . . ? C7 N3 Ru1 116.06(16) . . ? C16 N3 Ru1 126.14(15) . . ? C26 N4 C28 120.9(2) . . ? C26 N4 C27 120.5(2) . . ? C28 N4 C27 118.6(2) . . ? N1 C1 C2 119.7(2) . . ? N1 C1 C6 114.3(2) . . ? C2 C1 C6 126.0(2) . . ? C3 C2 C1 118.3(2) . . ? C3 C2 H3 120.9 . . ? C1 C2 H3 120.9 . . ? C2 C3 C4 120.7(2) . . ? C2 C3 H4 119.6 . . ? C4 C3 H4 119.6 . . ? C5 C4 C3 118.7(2) . . ? C5 C4 H5 120.7 . . ? C3 C4 H5 120.7 . . ? N1 C5 C4 119.4(2) . . ? N1 C5 C7 113.5(2) . . ? C4 C5 C7 127.2(2) . . ? O1 C6 N2 128.4(2) . . ? O1 C6 C1 117.9(2) . . ? N2 C6 C1 113.7(2) . . ? O2 C7 N3 126.4(2) . . ? O2 C7 C5 119.3(2) . . ? N3 C7 C5 114.3(2) . . ? N2 C8 C9 112.52(19) . . ? N2 C8 H6 109.1 . . ? C9 C8 H6 109.1 . . ? N2 C8 H7 109.1 . . ? C9 C8 H7 109.1 . . ? H6 C8 H7 107.8 . . ? C14 C9 C10 117.8(2) . . ? C14 C9 C8 121.5(2) . . ? C10 C9 C8 120.8(2) . . ? C11 C10 C9 121.4(2) . . ? C11 C10 H8 119.3 . . ? C9 C10 H8 119.3 . . ? C10 C11 C12 120.0(2) . . ? C10 C11 H9 120.0 . . ? C12 C11 H9 120.0 . . ? O3 C12 C13 125.2(2) . . ? O3 C12 C11 115.2(2) . . ? C13 C12 C11 119.6(2) . . ? C12 C13 C14 119.2(2) . . ? C12 C13 H10 120.4 . . ? C14 C13 H10 120.4 . . ? C9 C14 C13 121.9(2) . . ? C9 C14 H11 119.0 . . ? C13 C14 H11 119.0 . . ? O3 C15 H12 109.5 . . ? O3 C15 H13 109.5 . . ? H12 C15 H13 109.5 . . ? O3 C15 H14 109.5 . . ? H12 C15 H14 109.5 . . ? H13 C15 H14 109.5 . . ? N3 C16 C17 111.4(2) . . ? N3 C16 H15 109.3 . . ? C17 C16 H15 109.3 . . ? N3 C16 H16 109.3 . . ? C17 C16 H16 109.3 . . ? H15 C16 H16 108.0 . . ? C22 C17 C18 118.1(2) . . ? C22 C17 C16 121.7(2) . . ? C18 C17 C16 120.2(2) . . ? C17 C18 C19 121.6(2) . . ? C17 C18 H17 119.2 . . ? C19 C18 H17 119.2 . . ? C20 C19 C18 119.2(2) . . ? C20 C19 H18 120.4 . . ? C18 C19 H18 120.4 . . ? C19 C20 O4 124.3(2) . . ? C19 C20 C21 120.1(2) . . ? O4 C20 C21 115.6(2) . . ? C20 C21 C22 120.0(2) . . ? C20 C21 H19 120.0 . . ? C22 C21 H19 120.0 . . ? C17 C22 C21 120.9(2) . . ? C17 C22 H20 119.6 . . ? C21 C22 H20 119.5 . . ? O4 C23 H21 109.5 . . ? O4 C23 H22 109.5 . . ? H21 C23 H22 109.5 . . ? O4 C23 H23 109.5 . . ? H21 C23 H23 109.5 . . ? H22 C23 H23 109.5 . . ? O5 C24 Ru1 179.7(3) . . ? O6 C25 Ru1 178.3(2) . . ? O8 C26 N4 125.7(3) . . ? O8 C26 H24 117.1 . . ? N4 C26 H24 117.1 . . ? N4 C27 H25 109.5 . . ? N4 C27 H26 109.5 . . ? H25 C27 H26 109.5 . . ? N4 C27 H27 109.5 . . ? H25 C27 H27 109.5 . . ? H26 C27 H27 109.5 . . ? N4 C28 H28 109.5 . . ? N4 C28 H29 109.5 . . ? H28 C28 H29 109.5 . . ? N4 C28 H30 109.5 . . ? H28 C28 H30 109.5 . . ? H29 C28 H30 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 C24 1.854(3) . ? Ru1 C25 1.903(3) . ? Ru1 N1 2.024(2) . ? Ru1 N3 2.100(2) . ? Ru1 N2 2.112(2) . ? Ru1 O7 2.1454(18) . ? O1 C6 1.260(3) . ? O2 C7 1.263(3) . ? O3 C12 1.370(3) . ? O3 C15 1.429(3) . ? O4 C20 1.385(3) . ? O4 C23 1.430(3) . ? O5 C24 1.146(3) . ? O6 C25 1.144(3) . ? O7 H1 0.82(3) . ? O7 H2 0.79(3) . ? O8 C26 1.228(4) . ? N1 C1 1.339(3) . ? N1 C5 1.349(3) . ? N2 C6 1.335(3) . ? N2 C8 1.470(3) . ? N3 C7 1.328(3) . ? N3 C16 1.479(3) . ? N4 C26 1.335(4) . ? N4 C28 1.447(4) . ? N4 C27 1.452(3) . ? C1 C2 1.391(3) . ? C1 C6 1.511(3) . ? C2 C3 1.389(3) . ? C2 H3 0.9500 . ? C3 C4 1.395(3) . ? C3 H4 0.9500 . ? C4 C5 1.383(3) . ? C4 H5 0.9500 . ? C5 C7 1.506(3) . ? C8 C9 1.511(3) . ? C8 H6 0.9900 . ? C8 H7 0.9900 . ? C9 C14 1.385(3) . ? C9 C10 1.396(3) . ? C10 C11 1.378(3) . ? C10 H8 0.9500 . ? C11 C12 1.402(3) . ? C11 H9 0.9500 . ? C12 C13 1.384(3) . ? C13 C14 1.398(3) . ? C13 H10 0.9500 . ? C14 H11 0.9500 . ? C15 H12 0.9800 . ? C15 H13 0.9800 . ? C15 H14 0.9800 . ? C16 C17 1.516(3) . ? C16 H15 0.9900 . ? C16 H16 0.9900 . ? C17 C22 1.389(3) . ? C17 C18 1.390(3) . ? C18 C19 1.395(3) . ? C18 H17 0.9500 . ? C19 C20 1.380(3) . ? C19 H18 0.9500 . ? C20 C21 1.388(4) . ? C21 C22 1.390(3) . ? C21 H19 0.9500 . ? C22 H20 0.9500 . ? C23 H21 0.9800 . ? C23 H22 0.9800 . ? C23 H23 0.9800 . ? C26 H24 0.9500 . ? C27 H25 0.9800 . ? C27 H26 0.9800 . ? C27 H27 0.9800 . ? C28 H28 0.9800 . ? C28 H29 0.9800 . ? C28 H30 0.9800 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag O7 H1 O1 . . 3_566 2.665(2) 0.82(3) 1.86(3) 172(3) no O7 H2 O2 . . 3_666 2.618(2) 0.79(3) 1.84(3) 168(3) no 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 C5 N1 C1 C2 -2.6(3) . . . . ? Ru1 N1 C1 C2 -177.58(16) . . . . ? C5 N1 C1 C6 175.2(2) . . . . ? Ru1 N1 C1 C6 0.2(3) . . . . ? N1 C1 C2 C3 -0.1(3) . . . . ? C6 C1 C2 C3 -177.6(2) . . . . ? C1 C2 C3 C4 2.3(3) . . . . ? C2 C3 C4 C5 -1.8(3) . . . . ? C1 N1 C5 C4 3.1(3) . . . . ? Ru1 N1 C5 C4 178.04(16) . . . . ? C1 N1 C5 C7 -176.6(2) . . . . ? Ru1 N1 C5 C7 -1.6(3) . . . . ? C3 C4 C5 N1 -0.8(3) . . . . ? C3 C4 C5 C7 178.8(2) . . . . ? C8 N2 C6 O1 1.2(4) . . . . ? Ru1 N2 C6 O1 -179.04(19) . . . . ? C8 N2 C6 C1 -178.29(18) . . . . ? Ru1 N2 C6 C1 1.5(2) . . . . ? N1 C1 C6 O1 179.3(2) . . . . ? C2 C1 C6 O1 -3.0(3) . . . . ? N1 C1 C6 N2 -1.1(3) . . . . ? C2 C1 C6 N2 176.5(2) . . . . ? C16 N3 C7 O2 5.8(3) . . . . ? Ru1 N3 C7 O2 178.46(18) . . . . ? C16 N3 C7 C5 -173.72(19) . . . . ? Ru1 N3 C7 C5 -1.1(3) . . . . ? N1 C5 C7 O2 -177.8(2) . . . . ? C4 C5 C7 O2 2.5(4) . . . . ? N1 C5 C7 N3 1.7(3) . . . . ? C4 C5 C7 N3 -177.9(2) . . . . ? C6 N2 C8 C9 -117.5(2) . . . . ? Ru1 N2 C8 C9 62.8(3) . . . . ? N2 C8 C9 C14 -128.0(2) . . . . ? N2 C8 C9 C10 53.0(3) . . . . ? C14 C9 C10 C11 -0.2(3) . . . . ? C8 C9 C10 C11 178.8(2) . . . . ? C9 C10 C11 C12 0.2(4) . . . . ? C15 O3 C12 C13 1.2(4) . . . . ? C15 O3 C12 C11 -178.5(2) . . . . ? C10 C11 C12 O3 179.7(2) . . . . ? C10 C11 C12 C13 -0.1(4) . . . . ? O3 C12 C13 C14 -179.7(2) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? C10 C9 C14 C13 0.2(4) . . . . ? C8 C9 C14 C13 -178.8(2) . . . . ? C12 C13 C14 C9 -0.1(4) . . . . ? C7 N3 C16 C17 96.9(2) . . . . ? Ru1 N3 C16 C17 -74.9(2) . . . . ? N3 C16 C17 C22 125.2(2) . . . . ? N3 C16 C17 C18 -55.5(3) . . . . ? C22 C17 C18 C19 0.6(4) . . . . ? C16 C17 C18 C19 -178.8(2) . . . . ? C17 C18 C19 C20 1.2(4) . . . . ? C18 C19 C20 O4 178.5(2) . . . . ? C18 C19 C20 C21 -2.2(4) . . . . ? C23 O4 C20 C19 -7.2(4) . . . . ? C23 O4 C20 C21 173.5(2) . . . . ? C19 C20 C21 C22 1.5(4) . . . . ? O4 C20 C21 C22 -179.2(2) . . . . ? C18 C17 C22 C21 -1.3(4) . . . . ? C16 C17 C22 C21 178.0(2) . . . . ? C20 C21 C22 C17 0.3(4) . . . . ? C28 N4 C26 O8 -177.8(3) . . . . ? C27 N4 C26 O8 1.7(4) . . . . ?