#------------------------------------------------------------------------------ #$Date: 2024-03-04 22:32:42 +0200 (Mon, 04 Mar 2024) $ #$Revision: 290224 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247860.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_7247860 loop_ _publ_author_name 'Deshmukh, Gopal' 'Rana, Thakur Rochak Kumar' 'Yadav, Nikita' 'Rajaraman, Gopalan' 'Murugavel, Ramaswamy' _publ_section_title ; A highly active and chemoselective homobimetallic ruthenium catalyst for one-pot reductive amination in water ; _journal_issue 3 _journal_name_full 'Green Chemistry' _journal_page_first 1610 _journal_page_last 1626 _journal_paper_doi 10.1039/D3GC03374K _journal_volume 26 _journal_year 2024 _chemical_formula_moiety 'C29 H36 Cl N O Ru' _chemical_formula_sum 'C29 H36 Cl N O Ru' _chemical_formula_weight 551.11 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-07-18 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-08-28 deposited with the CCDC. 2023-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.3510(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.39840(10) _cell_length_b 12.30260(10) _cell_length_c 18.3366(2) _cell_measurement_reflns_used 26802 _cell_measurement_temperature 104.5(7) _cell_measurement_theta_max 25.0270 _cell_measurement_theta_min 2.2440 _cell_volume 2537.17(4) _computing_cell_refinement 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_collection 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_data_reduction 'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 104.5(7) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \f -126.01 105.99 1.00 5.00 6.61 -9.84 -31.50 -- 232 2 \w -100.81 15.19 1.00 5.00 -- -9.84 -59.25 -51.92 116 3 \w -100.81 15.19 1.00 5.00 -- -9.84 -59.25-123.92 116 4 \w -100.81 15.19 1.00 5.00 -- -9.84 -59.25 164.08 116 5 \w -60.89 0.11 1.00 5.00 -- -14.77 94.56 -34.84 61 ; _diffrn_measurement_device 'abstract diffractometer' _diffrn_measurement_device_type 'Saxi-CrysAlisPro-abstract goniometer imported SAXI images' _diffrn_measurement_method '\w and \f scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0343273000 _diffrn_orient_matrix_UB_12 0.0477498000 _diffrn_orient_matrix_UB_13 0.0015899000 _diffrn_orient_matrix_UB_21 -0.0495906000 _diffrn_orient_matrix_UB_22 -0.0258992000 _diffrn_orient_matrix_UB_23 -0.0214170000 _diffrn_orient_matrix_UB_31 -0.0184909000 _diffrn_orient_matrix_UB_32 -0.0192443000 _diffrn_orient_matrix_UB_33 0.0328024000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_unetI/netI 0.0150 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 44264 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 25.019 _diffrn_reflns_theta_max 25.019 _diffrn_reflns_theta_min 2.251 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.745 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.63636 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic dark red' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.443 _exptl_crystal_description needle _exptl_crystal_F_000 1144 _exptl_crystal_size_max 0.201 _exptl_crystal_size_mid 0.057 _exptl_crystal_size_min 0.023 _refine_diff_density_max 0.446 _refine_diff_density_min -0.430 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 305 _refine_ls_number_reflns 4454 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0221 _refine_ls_R_factor_gt 0.0212 _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^)+(0.0261P)^2^+2.5289P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0542 _refine_ls_wR_factor_ref 0.0549 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4281 _reflns_number_total 4454 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03374k3.cif _cod_data_source_block rm_gd_312 _cod_depositor_comments 'Adding full bibliography for 7247859--7247860.cif.' _cod_database_code 7247860 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C14(H14), C17(H17), C26(H26) 2.b Aromatic/amide H refined with riding coordinates: C22(H22), C25(H25), C21(H21), C7(H7), C24(H24), C2(H2), C3(H3), C12(H12), C5(H5), C10(H10), C4(H4), C11(H11) 2.c Idealised Me refined as rotating group: C29(H29a,H29b,H29c), C27(H27a,H27b,H27c), C19(H19a,H19b,H19c), C16(H16a,H16b, H16c), C15(H15a,H15b,H15c), C28(H28a,H28b,H28c), C18(H18a,H18b,H18c) ; _shelx_res_file ; TITL rm_gd_312_a.res in P2(1)/n rm_gd_312.res created by SHELXL-2018/3 at 15:23:10 on 18-Jul-2023 REM Old TITL RM_GD_312 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.141, Rweak 0.006, Alpha 0.022 REM 1.340 for 236 systematic absences, Orientation as input REM Formula found by SHELXT: C29 N O2 Br CELL 0.71073 11.3984 12.3026 18.3366 90 99.351 90 ZERR 4 0.0001 0.0001 0.0002 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O Ru UNIT 116 144 4 4 4 4 L.S. 50 PLAN 5 TEMP -169 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.026100 2.528900 FVAR 0.54627 RU1 6 0.576542 0.607683 0.385575 11.00000 0.01507 0.01146 = 0.01030 0.00014 -0.00029 -0.00013 CL1 3 0.676603 0.695613 0.497850 11.00000 0.02328 0.01633 = 0.01313 -0.00093 -0.00156 -0.00127 O1 5 0.430460 0.688130 0.411298 11.00000 0.01842 0.01682 = 0.01879 -0.00241 0.00410 -0.00118 N1 4 0.616940 0.749899 0.330605 11.00000 0.01683 0.01502 = 0.01251 0.00078 -0.00069 -0.00043 C1 1 0.417611 0.792246 0.417067 11.00000 0.01926 0.02047 = 0.01250 -0.00135 -0.00321 0.00179 C22 1 0.583526 0.443752 0.435968 11.00000 0.02704 0.01028 = 0.01452 0.00075 0.00189 0.00173 AFIX 43 H22 2 0.582120 0.420130 0.485143 11.00000 -1.20000 AFIX 0 C25 1 0.585253 0.506750 0.289211 11.00000 0.02408 0.01248 = 0.01224 -0.00178 0.00233 0.00020 AFIX 43 H25 2 0.586727 0.527048 0.239381 11.00000 -1.20000 AFIX 0 C20 1 0.474465 0.486869 0.311779 11.00000 0.02153 0.01149 = 0.01575 -0.00212 -0.00052 -0.00083 C21 1 0.476793 0.454605 0.386863 11.00000 0.02078 0.01243 = 0.01832 -0.00157 0.00330 -0.00320 AFIX 43 H21 2 0.403911 0.440163 0.403831 11.00000 -1.20000 AFIX 0 C7 1 0.575154 0.845070 0.342616 11.00000 0.01985 0.01711 = 0.01521 0.00285 -0.00445 -0.00275 AFIX 43 H7 2 0.606445 0.904336 0.318672 11.00000 -1.20000 AFIX 0 C23 1 0.694614 0.467704 0.413185 11.00000 0.02174 0.01083 = 0.01739 -0.00188 -0.00064 0.00345 C24 1 0.694880 0.497354 0.338745 11.00000 0.01907 0.01335 = 0.01827 -0.00288 0.00321 0.00037 AFIX 43 H24 2 0.767934 0.510983 0.321777 11.00000 -1.20000 AFIX 0 C6 1 0.487666 0.871781 0.387525 11.00000 0.01961 0.01811 = 0.01426 -0.00008 -0.00375 0.00192 C8 1 0.689222 0.742193 0.272324 11.00000 0.02008 0.01214 = 0.01739 0.00238 0.00381 -0.00025 C9 1 0.814406 0.737169 0.291621 11.00000 0.02020 0.01483 = 0.02017 0.00518 0.00047 -0.00132 C2 1 0.323359 0.830881 0.452329 11.00000 0.02390 0.02496 = 0.01782 0.00052 0.00163 0.00404 AFIX 43 H2 2 0.273543 0.779918 0.471409 11.00000 -1.20000 AFIX 0 C13 1 0.632683 0.733938 0.198854 11.00000 0.02028 0.01202 = 0.01717 0.00263 0.00163 -0.00068 C14 1 0.497954 0.743591 0.176750 11.00000 0.01930 0.02324 = 0.01589 0.00350 -0.00042 -0.00076 AFIX 13 H14 2 0.460269 0.720556 0.219859 11.00000 -1.20000 AFIX 0 C17 1 0.873745 0.752139 0.371276 11.00000 0.02031 0.02668 = 0.01825 0.00651 -0.00128 -0.00325 AFIX 13 H17 2 0.817651 0.725162 0.403856 11.00000 -1.20000 AFIX 0 C29 1 0.807178 0.462706 0.468400 11.00000 0.02310 0.02222 = 0.02131 0.00042 -0.00338 0.00548 AFIX 137 H29A 2 0.864024 0.516098 0.455237 11.00000 -1.50000 H29B 2 0.841500 0.389689 0.468229 11.00000 -1.50000 H29C 2 0.789503 0.479066 0.517785 11.00000 -1.50000 AFIX 0 C3 1 0.302510 0.940491 0.459501 11.00000 0.02654 0.02994 = 0.02107 -0.00410 0.00242 0.00985 AFIX 43 H3 2 0.239670 0.963491 0.484145 11.00000 -1.20000 AFIX 0 C26 1 0.357733 0.492801 0.258367 11.00000 0.02081 0.02202 = 0.01675 0.00000 -0.00294 -0.00192 AFIX 13 H26 2 0.375023 0.521291 0.210150 11.00000 -1.20000 AFIX 0 C27 1 0.308845 0.376884 0.245534 11.00000 0.02120 0.02523 = 0.02892 -0.00834 -0.00155 -0.00200 AFIX 137 H27A 2 0.365915 0.332287 0.224173 11.00000 -1.50000 H27B 2 0.233115 0.378986 0.211487 11.00000 -1.50000 H27C 2 0.296297 0.345386 0.292749 11.00000 -1.50000 AFIX 0 C19 1 0.897355 0.873165 0.388498 11.00000 0.03755 0.03232 = 0.02163 0.00138 -0.00591 -0.00644 AFIX 137 H19A 2 0.956671 0.900335 0.359842 11.00000 -1.50000 H19B 2 0.927181 0.882129 0.441366 11.00000 -1.50000 H19C 2 0.823270 0.914213 0.375270 11.00000 -1.50000 AFIX 0 C12 1 0.703743 0.717168 0.144533 11.00000 0.02873 0.01547 = 0.01562 0.00172 0.00220 -0.00005 AFIX 43 H12 2 0.667044 0.709997 0.094411 11.00000 -1.20000 AFIX 0 C5 1 0.461704 0.983554 0.395237 11.00000 0.02584 0.01726 = 0.01936 -0.00008 -0.00416 -0.00030 AFIX 43 H5 2 0.508036 1.036120 0.374762 11.00000 -1.20000 AFIX 0 C16 1 0.461874 0.862234 0.158106 11.00000 0.02300 0.02923 = 0.02469 0.00413 0.00102 0.00593 AFIX 137 H16A 2 0.483170 0.907457 0.202270 11.00000 -1.50000 H16B 2 0.375857 0.866099 0.141286 11.00000 -1.50000 H16C 2 0.503629 0.888659 0.118894 11.00000 -1.50000 AFIX 0 C10 1 0.880372 0.721197 0.234959 11.00000 0.01888 0.01911 = 0.02769 0.00555 0.00363 0.00089 AFIX 43 H10 2 0.964583 0.717351 0.246572 11.00000 -1.20000 AFIX 0 C4 1 0.372315 1.018363 0.431109 11.00000 0.02958 0.01924 = 0.02483 -0.00500 -0.00570 0.00802 AFIX 43 H4 2 0.357975 1.093753 0.436612 11.00000 -1.20000 AFIX 0 C11 1 0.826048 0.710773 0.161985 11.00000 0.02640 0.01687 = 0.02341 0.00204 0.00921 0.00198 AFIX 43 H11 2 0.872684 0.699294 0.124191 11.00000 -1.20000 AFIX 0 C15 1 0.447675 0.672256 0.110552 11.00000 0.02754 0.03152 = 0.01909 0.00253 -0.00478 -0.00334 AFIX 137 H15A 2 0.469341 0.703335 0.065359 11.00000 -1.50000 H15B 2 0.360883 0.669025 0.105996 11.00000 -1.50000 H15C 2 0.480632 0.598764 0.117945 11.00000 -1.50000 AFIX 0 C28 1 0.265156 0.567212 0.284170 11.00000 0.02209 0.02483 = 0.03230 -0.00541 -0.00719 0.00212 AFIX 137 H28A 2 0.246613 0.540740 0.331405 11.00000 -1.50000 H28B 2 0.192670 0.567316 0.247189 11.00000 -1.50000 H28C 2 0.296845 0.641273 0.290454 11.00000 -1.50000 AFIX 0 C18 1 0.990187 0.688942 0.390773 11.00000 0.02337 0.04174 = 0.03114 0.01088 -0.00407 0.00024 AFIX 137 H18A 2 0.977834 0.613498 0.374136 11.00000 -1.50000 H18B 2 1.015992 0.690319 0.444418 11.00000 -1.50000 H18C 2 1.051336 0.722519 0.366255 11.00000 -1.50000 AFIX 0 HKLF 4 REM rm_gd_312_a.res in P2(1)/n REM wR2 = 0.0549, GooF = S = 1.033, Restrained GooF = 1.033 for all data REM R1 = 0.0212 for 4281 Fo > 4sig(Fo) and 0.0221 for all 4454 data REM 305 parameters refined using 0 restraints END WGHT 0.0261 2.5288 REM Highest difference peak 0.446, deepest hole -0.430, 1-sigma level 0.055 Q1 1 0.3984 0.7305 0.3872 11.00000 0.05 0.45 Q2 1 0.5713 0.8814 0.3883 11.00000 0.05 0.38 Q3 1 0.7560 0.7416 0.2858 11.00000 0.05 0.35 Q4 1 0.6610 0.6216 0.3668 11.00000 0.05 0.34 Q5 1 0.8415 0.7414 0.3288 11.00000 0.05 0.32 ; _shelx_res_checksum 54599 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.555 _oxdiff_exptl_absorpt_empirical_full_min 0.501 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 0.57654(2) 0.60768(2) 0.38558(2) 0.01254(6) Uani 1 1 d . . . . . Cl1 Cl 0.67660(4) 0.69561(3) 0.49785(2) 0.01808(10) Uani 1 1 d . . . . . O1 O 0.43046(11) 0.68813(10) 0.41130(7) 0.0179(3) Uani 1 1 d . . . . . N1 N 0.61694(13) 0.74990(12) 0.33061(8) 0.0151(3) Uani 1 1 d . . . . . C1 C 0.41761(16) 0.79225(15) 0.41707(10) 0.0181(4) Uani 1 1 d . . . . . C22 C 0.58353(17) 0.44375(14) 0.43597(10) 0.0174(4) Uani 1 1 d . . . . . H22 H 0.582120 0.420130 0.485143 0.021 Uiso 1 1 calc R U . . . C25 C 0.58525(16) 0.50675(14) 0.28921(10) 0.0163(4) Uani 1 1 d . . . . . H25 H 0.586727 0.527048 0.239381 0.020 Uiso 1 1 calc R U . . . C20 C 0.47447(16) 0.48687(14) 0.31178(10) 0.0166(4) Uani 1 1 d . . . . . C21 C 0.47679(17) 0.45460(14) 0.38686(10) 0.0172(4) Uani 1 1 d . . . . . H21 H 0.403911 0.440163 0.403831 0.021 Uiso 1 1 calc R U . . . C7 C 0.57515(16) 0.84507(15) 0.34262(10) 0.0182(4) Uani 1 1 d . . . . . H7 H 0.606445 0.904336 0.318672 0.022 Uiso 1 1 calc R U . . . C23 C 0.69461(16) 0.46770(14) 0.41319(10) 0.0171(4) Uani 1 1 d . . . . . C24 C 0.69488(16) 0.49735(14) 0.33875(10) 0.0169(4) Uani 1 1 d . . . . . H24 H 0.767934 0.510983 0.321777 0.020 Uiso 1 1 calc R U . . . C6 C 0.48767(16) 0.87178(15) 0.38753(10) 0.0180(4) Uani 1 1 d . . . . . C8 C 0.68922(16) 0.74219(14) 0.27232(10) 0.0165(4) Uani 1 1 d . . . . . C9 C 0.81441(16) 0.73717(15) 0.29162(10) 0.0187(4) Uani 1 1 d . . . . . C2 C 0.32336(17) 0.83088(16) 0.45233(10) 0.0224(4) Uani 1 1 d . . . . . H2 H 0.273543 0.779918 0.471409 0.027 Uiso 1 1 calc R U . . . C13 C 0.63268(16) 0.73394(14) 0.19885(10) 0.0166(4) Uani 1 1 d . . . . . C14 C 0.49795(16) 0.74359(15) 0.17675(10) 0.0198(4) Uani 1 1 d . . . . . H14 H 0.460269 0.720556 0.219859 0.024 Uiso 1 1 calc R U . . . C17 C 0.87375(17) 0.75214(16) 0.37128(10) 0.0222(4) Uani 1 1 d . . . . . H17 H 0.817651 0.725162 0.403856 0.027 Uiso 1 1 calc R U . . . C29 C 0.80718(17) 0.46271(16) 0.46840(11) 0.0230(4) Uani 1 1 d . . . . . H29A H 0.864024 0.516098 0.455237 0.034 Uiso 1 1 calc R U . . . H29B H 0.841500 0.389689 0.468229 0.034 Uiso 1 1 calc R U . . . H29C H 0.789503 0.479066 0.517785 0.034 Uiso 1 1 calc R U . . . C3 C 0.30251(18) 0.94049(17) 0.45950(11) 0.0260(4) Uani 1 1 d . . . . . H3 H 0.239670 0.963491 0.484145 0.031 Uiso 1 1 calc R U . . . C26 C 0.35773(17) 0.49280(16) 0.25837(10) 0.0205(4) Uani 1 1 d . . . . . H26 H 0.375023 0.521291 0.210150 0.025 Uiso 1 1 calc R U . . . C27 C 0.30884(18) 0.37688(16) 0.24553(12) 0.0257(4) Uani 1 1 d . . . . . H27A H 0.365915 0.332287 0.224173 0.039 Uiso 1 1 calc R U . . . H27B H 0.233115 0.378986 0.211487 0.039 Uiso 1 1 calc R U . . . H27C H 0.296297 0.345386 0.292749 0.039 Uiso 1 1 calc R U . . . C19 C 0.8974(2) 0.87317(18) 0.38850(12) 0.0317(5) Uani 1 1 d . . . . . H19A H 0.956671 0.900335 0.359842 0.048 Uiso 1 1 calc R U . . . H19B H 0.927181 0.882129 0.441366 0.048 Uiso 1 1 calc R U . . . H19C H 0.823270 0.914213 0.375270 0.048 Uiso 1 1 calc R U . . . C12 C 0.70374(17) 0.71717(15) 0.14453(10) 0.0201(4) Uani 1 1 d . . . . . H12 H 0.667044 0.709997 0.094411 0.024 Uiso 1 1 calc R U . . . C5 C 0.46170(17) 0.98355(15) 0.39524(10) 0.0217(4) Uani 1 1 d . . . . . H5 H 0.508036 1.036120 0.374762 0.026 Uiso 1 1 calc R U . . . C16 C 0.46187(18) 0.86223(17) 0.15811(11) 0.0260(4) Uani 1 1 d . . . . . H16A H 0.483170 0.907457 0.202270 0.039 Uiso 1 1 calc R U . . . H16B H 0.375857 0.866099 0.141286 0.039 Uiso 1 1 calc R U . . . H16C H 0.503629 0.888659 0.118894 0.039 Uiso 1 1 calc R U . . . C10 C 0.88037(17) 0.72120(15) 0.23496(11) 0.0219(4) Uani 1 1 d . . . . . H10 H 0.964583 0.717351 0.246572 0.026 Uiso 1 1 calc R U . . . C4 C 0.37231(18) 1.01836(16) 0.43111(11) 0.0257(4) Uani 1 1 d . . . . . H4 H 0.357975 1.093753 0.436612 0.031 Uiso 1 1 calc R U . . . C11 C 0.82605(18) 0.71077(15) 0.16199(11) 0.0217(4) Uani 1 1 d . . . . . H11 H 0.872684 0.699294 0.124191 0.026 Uiso 1 1 calc R U . . . C15 C 0.44768(19) 0.67226(18) 0.11055(11) 0.0270(4) Uani 1 1 d . . . . . H15A H 0.469341 0.703335 0.065359 0.041 Uiso 1 1 calc R U . . . H15B H 0.360883 0.669025 0.105996 0.041 Uiso 1 1 calc R U . . . H15C H 0.480632 0.598764 0.117945 0.041 Uiso 1 1 calc R U . . . C28 C 0.26516(18) 0.56721(17) 0.28417(12) 0.0277(5) Uani 1 1 d . . . . . H28A H 0.246613 0.540740 0.331405 0.042 Uiso 1 1 calc R U . . . H28B H 0.192670 0.567316 0.247189 0.042 Uiso 1 1 calc R U . . . H28C H 0.296845 0.641273 0.290454 0.042 Uiso 1 1 calc R U . . . C18 C 0.99019(19) 0.6889(2) 0.39077(12) 0.0330(5) Uani 1 1 d . . . . . H18A H 0.977834 0.613498 0.374136 0.050 Uiso 1 1 calc R U . . . H18B H 1.015992 0.690319 0.444418 0.050 Uiso 1 1 calc R U . . . H18C H 1.051336 0.722519 0.366255 0.050 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 0.01507(9) 0.01146(9) 0.01030(9) 0.00014(5) -0.00029(6) -0.00013(5) Cl1 0.0233(2) 0.0163(2) 0.0131(2) -0.00093(16) -0.00156(17) -0.00127(17) O1 0.0184(6) 0.0168(6) 0.0188(6) -0.0024(5) 0.0041(5) -0.0012(5) N1 0.0168(8) 0.0150(8) 0.0125(7) 0.0008(6) -0.0007(6) -0.0004(6) C1 0.0193(9) 0.0205(9) 0.0125(8) -0.0014(7) -0.0032(7) 0.0018(7) C22 0.0270(10) 0.0103(8) 0.0145(9) 0.0008(7) 0.0019(7) 0.0017(7) C25 0.0241(10) 0.0125(8) 0.0122(8) -0.0018(7) 0.0023(7) 0.0002(7) C20 0.0215(9) 0.0115(8) 0.0157(9) -0.0021(7) -0.0005(7) -0.0008(7) C21 0.0208(9) 0.0124(8) 0.0183(9) -0.0016(7) 0.0033(7) -0.0032(7) C7 0.0198(9) 0.0171(9) 0.0152(9) 0.0029(7) -0.0044(7) -0.0027(7) C23 0.0217(9) 0.0108(8) 0.0174(9) -0.0019(7) -0.0006(7) 0.0035(7) C24 0.0191(9) 0.0133(8) 0.0183(9) -0.0029(7) 0.0032(7) 0.0004(7) C6 0.0196(9) 0.0181(9) 0.0143(9) -0.0001(7) -0.0037(7) 0.0019(7) C8 0.0201(9) 0.0121(8) 0.0174(9) 0.0024(7) 0.0038(7) -0.0003(7) C9 0.0202(9) 0.0148(9) 0.0202(9) 0.0052(7) 0.0005(8) -0.0013(7) C2 0.0239(10) 0.0250(10) 0.0178(9) 0.0005(8) 0.0016(8) 0.0040(8) C13 0.0203(9) 0.0120(8) 0.0172(9) 0.0026(7) 0.0016(7) -0.0007(7) C14 0.0193(9) 0.0232(10) 0.0159(9) 0.0035(7) -0.0004(7) -0.0008(8) C17 0.0203(10) 0.0267(10) 0.0183(9) 0.0065(8) -0.0013(8) -0.0032(8) C29 0.0231(10) 0.0222(10) 0.0213(10) 0.0004(8) -0.0034(8) 0.0055(8) C3 0.0265(10) 0.0299(11) 0.0211(10) -0.0041(8) 0.0024(8) 0.0098(9) C26 0.0208(10) 0.0220(10) 0.0167(9) 0.0000(7) -0.0029(7) -0.0019(8) C27 0.0212(10) 0.0252(10) 0.0289(11) -0.0083(8) -0.0015(8) -0.0020(8) C19 0.0376(13) 0.0323(12) 0.0216(10) 0.0014(9) -0.0059(9) -0.0064(10) C12 0.0287(10) 0.0155(9) 0.0156(9) 0.0017(7) 0.0022(8) -0.0001(8) C5 0.0258(10) 0.0173(9) 0.0194(9) -0.0001(7) -0.0042(8) -0.0003(8) C16 0.0230(10) 0.0292(11) 0.0247(10) 0.0041(9) 0.0010(8) 0.0059(9) C10 0.0189(9) 0.0191(9) 0.0277(10) 0.0055(8) 0.0036(8) 0.0009(8) C4 0.0296(11) 0.0192(10) 0.0248(10) -0.0050(8) -0.0057(8) 0.0080(8) C11 0.0264(10) 0.0169(9) 0.0234(10) 0.0020(8) 0.0092(8) 0.0020(8) C15 0.0275(11) 0.0315(11) 0.0191(10) 0.0025(8) -0.0048(8) -0.0033(9) C28 0.0221(10) 0.0248(11) 0.0323(11) -0.0054(9) -0.0072(9) 0.0021(8) C18 0.0234(11) 0.0417(13) 0.0311(12) 0.0109(10) -0.0041(9) 0.0002(9) 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 O1 Ru1 Cl1 82.99(4) . . ? O1 Ru1 N1 87.60(5) . . ? O1 Ru1 C22 108.55(6) . . ? O1 Ru1 C25 127.34(6) . . ? O1 Ru1 C20 95.67(6) . . ? O1 Ru1 C21 88.30(6) . . ? O1 Ru1 C23 144.50(6) . . ? O1 Ru1 C24 164.46(6) . . ? N1 Ru1 Cl1 85.81(4) . . ? N1 Ru1 C22 163.74(6) . . ? N1 Ru1 C25 92.47(6) . . ? N1 Ru1 C20 113.57(6) . . ? N1 Ru1 C21 150.30(6) . . ? N1 Ru1 C23 126.07(6) . . ? N1 Ru1 C24 97.52(6) . . ? C22 Ru1 Cl1 94.10(5) . . ? C25 Ru1 Cl1 149.57(5) . . ? C25 Ru1 C22 79.38(7) . . ? C25 Ru1 C20 37.58(7) . . ? C25 Ru1 C21 67.19(7) . . ? C25 Ru1 C23 68.41(7) . . ? C25 Ru1 C24 38.15(7) . . ? C20 Ru1 Cl1 160.55(5) . . ? C20 Ru1 C22 67.83(6) . . ? C21 Ru1 Cl1 122.81(5) . . ? C21 Ru1 C22 36.89(7) . . ? C21 Ru1 C20 37.80(6) . . ? C23 Ru1 Cl1 88.18(5) . . ? C23 Ru1 C22 37.78(7) . . ? C23 Ru1 C20 81.69(7) . . ? C23 Ru1 C21 67.95(7) . . ? C24 Ru1 Cl1 111.93(5) . . ? C24 Ru1 C22 67.40(7) . . ? C24 Ru1 C20 68.82(7) . . ? C24 Ru1 C21 79.96(7) . . ? C24 Ru1 C23 37.66(7) . . ? C1 O1 Ru1 126.94(12) . . ? C7 N1 Ru1 123.63(13) . . ? C7 N1 C8 116.83(15) . . ? C8 N1 Ru1 119.42(11) . . ? O1 C1 C6 124.77(17) . . ? O1 C1 C2 118.11(17) . . ? C2 C1 C6 117.05(17) . . ? Ru1 C22 H22 132.0 . . ? C21 C22 Ru1 71.07(10) . . ? C21 C22 H22 119.6 . . ? C21 C22 C23 120.84(16) . . ? C23 C22 Ru1 70.32(10) . . ? C23 C22 H22 119.6 . . ? Ru1 C25 H25 129.9 . . ? C20 C25 Ru1 72.54(10) . . ? C20 C25 H25 118.9 . . ? C20 C25 C24 122.16(16) . . ? C24 C25 Ru1 71.31(10) . . ? C24 C25 H25 118.9 . . ? C25 C20 Ru1 69.89(10) . . ? C25 C20 C21 116.92(16) . . ? C25 C20 C26 122.24(16) . . ? C21 C20 Ru1 70.81(10) . . ? C21 C20 C26 120.75(16) . . ? C26 C20 Ru1 132.91(13) . . ? Ru1 C21 H21 130.1 . . ? C22 C21 Ru1 72.04(10) . . ? C22 C21 C20 121.69(17) . . ? C22 C21 H21 119.2 . . ? C20 C21 Ru1 71.39(10) . . ? C20 C21 H21 119.2 . . ? N1 C7 H7 116.0 . . ? N1 C7 C6 127.94(17) . . ? C6 C7 H7 116.0 . . ? C22 C23 Ru1 71.90(10) . . ? C22 C23 C29 119.73(16) . . ? C24 C23 Ru1 70.85(10) . . ? C24 C23 C22 118.51(16) . . ? C24 C23 C29 121.75(17) . . ? C29 C23 Ru1 127.81(13) . . ? Ru1 C24 H24 130.5 . . ? C25 C24 Ru1 70.54(10) . . ? C25 C24 H24 120.1 . . ? C23 C24 Ru1 71.49(10) . . ? C23 C24 C25 119.82(17) . . ? C23 C24 H24 120.1 . . ? C1 C6 C7 123.18(17) . . ? C5 C6 C1 119.28(17) . . ? C5 C6 C7 117.14(17) . . ? C9 C8 N1 119.20(16) . . ? C13 C8 N1 119.00(16) . . ? C13 C8 C9 121.71(17) . . ? C8 C9 C17 120.60(17) . . ? C10 C9 C8 117.69(17) . . ? C10 C9 C17 121.68(17) . . ? C1 C2 H2 119.2 . . ? C3 C2 C1 121.64(19) . . ? C3 C2 H2 119.2 . . ? C8 C13 C14 122.38(16) . . ? C12 C13 C8 117.86(17) . . ? C12 C13 C14 119.76(16) . . ? C13 C14 H14 108.1 . . ? C13 C14 C16 110.69(15) . . ? C13 C14 C15 113.34(16) . . ? C16 C14 H14 108.1 . . ? C15 C14 H14 108.1 . . ? C15 C14 C16 108.37(16) . . ? C9 C17 H17 107.8 . . ? C9 C17 C19 110.56(16) . . ? C9 C17 C18 113.41(17) . . ? C19 C17 H17 107.8 . . ? C18 C17 H17 107.8 . . ? C18 C17 C19 109.16(17) . . ? C23 C29 H29A 109.5 . . ? C23 C29 H29B 109.5 . . ? C23 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C2 C3 H3 119.4 . . ? C2 C3 C4 121.12(19) . . ? C4 C3 H3 119.4 . . ? C20 C26 H26 108.0 . . ? C20 C26 C27 108.18(15) . . ? C20 C26 C28 113.90(15) . . ? C27 C26 H26 108.0 . . ? C28 C26 H26 108.0 . . ? C28 C26 C27 110.61(16) . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C13 C12 H12 119.2 . . ? C11 C12 C13 121.56(18) . . ? C11 C12 H12 119.2 . . ? C6 C5 H5 118.8 . . ? C4 C5 C6 122.35(19) . . ? C4 C5 H5 118.8 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C10 H10 119.2 . . ? C11 C10 C9 121.53(18) . . ? C11 C10 H10 119.2 . . ? C3 C4 H4 120.7 . . ? C5 C4 C3 118.53(18) . . ? C5 C4 H4 120.7 . . ? C12 C11 C10 119.62(18) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C26 C28 H28A 109.5 . . ? C26 C28 H28B 109.5 . . ? C26 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 Cl1 2.4385(4) . ? Ru1 O1 2.0566(12) . ? Ru1 N1 2.1071(15) . ? Ru1 C22 2.2144(17) . ? Ru1 C25 2.1751(17) . ? Ru1 C20 2.2096(17) . ? Ru1 C21 2.2020(18) . ? Ru1 C23 2.1936(17) . ? Ru1 C24 2.1853(18) . ? O1 C1 1.296(2) . ? N1 C7 1.296(2) . ? N1 C8 1.455(2) . ? C1 C6 1.424(3) . ? C1 C2 1.423(3) . ? C22 H22 0.9500 . ? C22 C21 1.397(3) . ? C22 C23 1.427(3) . ? C25 H25 0.9500 . ? C25 C20 1.413(3) . ? C25 C24 1.425(3) . ? C20 C21 1.429(2) . ? C20 C26 1.520(2) . ? C21 H21 0.9500 . ? C7 H7 0.9500 . ? C7 C6 1.431(3) . ? C23 C24 1.413(3) . ? C23 C29 1.501(3) . ? C24 H24 0.9500 . ? C6 C5 1.418(3) . ? C8 C9 1.415(3) . ? C8 C13 1.399(3) . ? C9 C17 1.518(3) . ? C9 C10 1.392(3) . ? C2 H2 0.9500 . ? C2 C3 1.379(3) . ? C13 C14 1.528(3) . ? C13 C12 1.397(3) . ? C14 H14 1.0000 . ? C14 C16 1.540(3) . ? C14 C15 1.532(3) . ? C17 H17 1.0000 . ? C17 C19 1.537(3) . ? C17 C18 1.530(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C3 H3 0.9500 . ? C3 C4 1.399(3) . ? C26 H26 1.0000 . ? C26 C27 1.535(3) . ? C26 C28 1.529(3) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C12 H12 0.9500 . ? C12 C11 1.381(3) . ? C5 H5 0.9500 . ? C5 C4 1.368(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C10 H10 0.9500 . ? C10 C11 1.386(3) . ? C4 H4 0.9500 . ? C11 H11 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 Ru1 O1 C1 C6 18.1(2) . . . . ? Ru1 O1 C1 C2 -165.07(12) . . . . ? Ru1 N1 C7 C6 -6.8(3) . . . . ? Ru1 N1 C8 C9 -82.02(18) . . . . ? Ru1 N1 C8 C13 94.51(17) . . . . ? Ru1 C22 C21 C20 53.53(15) . . . . ? Ru1 C22 C23 C24 -55.24(14) . . . . ? Ru1 C22 C23 C29 123.78(16) . . . . ? Ru1 C25 C20 C21 -54.65(14) . . . . ? Ru1 C25 C20 C26 128.77(16) . . . . ? Ru1 C25 C24 C23 53.80(15) . . . . ? Ru1 C20 C21 C22 -53.82(15) . . . . ? Ru1 C20 C26 C27 -158.66(15) . . . . ? Ru1 C20 C26 C28 -35.2(3) . . . . ? Ru1 C23 C24 C25 -53.35(15) . . . . ? O1 C1 C6 C7 5.1(3) . . . . ? O1 C1 C6 C5 177.64(17) . . . . ? O1 C1 C2 C3 -178.86(17) . . . . ? N1 C7 C6 C1 -10.9(3) . . . . ? N1 C7 C6 C5 176.43(18) . . . . ? N1 C8 C9 C17 -6.7(2) . . . . ? N1 C8 C9 C10 175.03(16) . . . . ? N1 C8 C13 C14 6.0(3) . . . . ? N1 C8 C13 C12 -174.56(15) . . . . ? C1 C6 C5 C4 0.9(3) . . . . ? C1 C2 C3 C4 1.1(3) . . . . ? C22 C23 C24 Ru1 55.76(14) . . . . ? C22 C23 C24 C25 2.4(2) . . . . ? C25 C20 C21 Ru1 54.19(14) . . . . ? C25 C20 C21 C22 0.4(3) . . . . ? C25 C20 C26 C27 109.55(19) . . . . ? C25 C20 C26 C28 -127.02(19) . . . . ? C20 C25 C24 Ru1 -54.07(15) . . . . ? C20 C25 C24 C23 -0.3(3) . . . . ? C21 C22 C23 Ru1 52.06(15) . . . . ? C21 C22 C23 C24 -3.2(3) . . . . ? C21 C22 C23 C29 175.84(16) . . . . ? C21 C20 C26 C27 -66.9(2) . . . . ? C21 C20 C26 C28 56.5(2) . . . . ? C7 N1 C8 C9 101.88(19) . . . . ? C7 N1 C8 C13 -81.6(2) . . . . ? C7 C6 C5 C4 173.91(17) . . . . ? C23 C22 C21 Ru1 -51.73(15) . . . . ? C23 C22 C21 C20 1.8(3) . . . . ? C24 C25 C20 Ru1 53.52(15) . . . . ? C24 C25 C20 C21 -1.1(3) . . . . ? C24 C25 C20 C26 -177.71(16) . . . . ? C6 C1 C2 C3 -1.7(3) . . . . ? C6 C5 C4 C3 -1.6(3) . . . . ? C8 N1 C7 C6 169.15(17) . . . . ? C8 C9 C17 C19 -87.6(2) . . . . ? C8 C9 C17 C18 149.43(18) . . . . ? C8 C9 C10 C11 0.2(3) . . . . ? C8 C13 C14 C16 91.5(2) . . . . ? C8 C13 C14 C15 -146.53(17) . . . . ? C8 C13 C12 C11 -1.1(3) . . . . ? C9 C8 C13 C14 -177.58(16) . . . . ? C9 C8 C13 C12 1.9(3) . . . . ? C9 C10 C11 C12 0.5(3) . . . . ? C2 C1 C6 C7 -171.81(17) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? C13 C8 C9 C17 176.84(17) . . . . ? C13 C8 C9 C10 -1.4(3) . . . . ? C13 C12 C11 C10 0.0(3) . . . . ? C14 C13 C12 C11 178.32(17) . . . . ? C17 C9 C10 C11 -178.06(17) . . . . ? C29 C23 C24 Ru1 -123.25(17) . . . . ? C29 C23 C24 C25 -176.60(16) . . . . ? C26 C20 C21 Ru1 -129.18(16) . . . . ? C26 C20 C21 C22 176.99(16) . . . . ? C12 C13 C14 C16 -88.0(2) . . . . ? C12 C13 C14 C15 34.0(2) . . . . ? C10 C9 C17 C19 90.6(2) . . . . ? C10 C9 C17 C18 -32.4(3) . . . . ?