#------------------------------------------------------------------------------ #$Date: 2022-05-05 23:18:04 +0300 (Thu, 05 May 2022) $ #$Revision: 274939 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566090.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_1566090 loop_ _publ_author_name 'B\"uhler, Jan' 'Zurfl\"uh, Jonas' 'Siol, Sebastian' 'Blacque, Olivier' 'S\'every, Laurent' 'Tilley, S. David' _publ_section_title ; Electrochemical ruthenium-catalysed C--H activation in water through heterogenization of a molecular catalyst ; _journal_issue 5 _journal_name_full 'Catalysis Science & Technology' _journal_page_first 1512 _journal_page_last 1519 _journal_paper_doi 10.1039/D1CY01999F _journal_volume 12 _journal_year 2022 _chemical_formula_moiety 'C21 H16 Cl N4 O5 P Ru' _chemical_formula_sum 'C21 H16 Cl N4 O5 P Ru' _chemical_formula_weight 571.87 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-02-05 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226) ; _audit_update_record ; 2021-07-05 deposited with the CCDC. 2022-01-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.0515(14) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.06525(17) _cell_length_b 25.1567(4) _cell_length_c 13.9309(2) _cell_measurement_reflns_used 12726 _cell_measurement_temperature 160(1) _cell_measurement_theta_max 78.6050 _cell_measurement_theta_min 3.6240 _cell_volume 4853.59(12) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT (Sheldrick, 2015a)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 160(1) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 200K' _diffrn_measured_fraction_theta_full 0.999 _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 \w -128.00 -35.00 0.50 5.00 -- -49.87 -34.00 149.00 186 2 \w -65.00 29.00 0.50 5.00 -- -49.87 34.00 -52.00 188 3 \w -167.00 -73.00 0.50 20.00 -- -88.50 -34.00 149.00 188 4 \w -103.00 -10.00 0.50 20.00 -- -88.50 34.00 -52.00 186 5 \w 95.00 178.00 0.50 20.00 -- 110.00 34.00 -52.00 166 6 \w 32.00 125.00 0.50 20.00 -- 110.00 -34.00 149.00 186 7 \w -125.00 -73.00 0.50 5.00 -- -49.87-125.00-120.00 104 8 \w -125.00 -73.00 0.50 5.00 -- -49.87-125.00 -90.00 104 9 \w 35.00 128.00 0.50 5.00 -- 49.87 34.00 -52.00 186 10 \w -83.00 -11.00 0.50 20.00 -- -88.50 111.00 30.00 144 11 \w 94.00 178.00 0.50 20.00 -- 110.00 15.00 60.00 168 12 \w 31.00 125.00 0.50 20.00 -- 110.00 -30.00 30.00 188 13 \w 31.00 125.00 0.50 20.00 -- 110.00 -30.00 -60.00 188 14 \w 62.00 146.00 0.50 20.00 -- 110.00 178.00-180.00 168 15 \w 34.00 107.00 0.50 20.00 -- 110.00 -94.00 120.00 146 16 \w 34.00 107.00 0.50 20.00 -- 110.00 -94.00-180.00 146 17 \w 48.00 78.00 0.50 20.00 -- 110.00 -61.00 30.00 60 18 \w 83.00 109.00 0.50 20.00 -- 110.00 -61.00 30.00 52 19 \w 104.00 176.00 0.50 20.00 -- 110.00 45.00 -90.00 144 20 \w 44.00 70.00 0.50 20.00 -- 110.00 -94.00-150.00 52 21 \w 36.00 108.00 0.50 20.00 -- 110.00-111.00 120.00 144 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 200K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0182675000 _diffrn_orient_matrix_UB_12 0.0175411000 _diffrn_orient_matrix_UB_13 -0.1011823000 _diffrn_orient_matrix_UB_21 -0.1048577000 _diffrn_orient_matrix_UB_22 0.0199747000 _diffrn_orient_matrix_UB_23 -0.0256800000 _diffrn_orient_matrix_UB_31 0.0321307000 _diffrn_orient_matrix_UB_32 0.0551950000 _diffrn_orient_matrix_UB_33 0.0414438000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_unetI/netI 0.0404 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 24717 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 74.498 _diffrn_reflns_theta_min 3.514 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 7.208 _exptl_absorpt_correction_T_max 0.914 _exptl_absorpt_correction_T_min 0.517 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'dark red' _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.565 _exptl_crystal_description needle _exptl_crystal_F_000 2288 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.015 _refine_diff_density_max 2.404 _refine_diff_density_min -0.601 _refine_diff_density_rms 0.157 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 304 _refine_ls_number_reflns 4949 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0518 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1028P)^2^+1.5763P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1359 _refine_ls_wR_factor_ref 0.1444 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4067 _reflns_number_total 4949 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1cy01999f2.cif _cod_data_source_block 3 _cod_depositor_comments 'Adding full bibliography for 1566090.cif.' _cod_original_cell_volume 4853.58(13) _cod_database_code 1566090 _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_max 0.900 _shelx_estimated_absorpt_t_min 0.374 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C18(H18), C20(H20), C21(H21) ; _shelx_res_file ; TITL janb0402_a.res in C2/c janb0402.res created by SHELXL-2018/3 at 11:14:35 on 05-Feb-2021 CELL 1.54184 14.065246 25.156733 13.93087 90 100.0515 90 ZERR 8 0.000174 0.000428 0.00024 0 0.0014 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H Cl N O P Ru UNIT 168 128 8 32 40 8 8 EQIV $1 0.5-X,1.5-Y,-Z EQIV $2 +X,1-Y,0.5+Z EQIV $3 0.5+X,1.5-Y,0.5+Z L.S. 9 PLAN 30 SIZE 0.015 0.015 0.17 TEMP -113.1(10) CONF HTAB O4 O3_$1 HTAB C12 O3_$2 HTAB C2 O4_$3 BOND list 4 MORE -1 BOND $H fmap 2 53 acta OMIT -1 1 1 REM REM REM WGHT 0.102800 1.576300 FVAR 0.40187 C1 1 0.393512 0.644184 0.444572 11.00000 0.04004 0.05282 = 0.07659 -0.00685 -0.00125 -0.00269 AFIX 43 H1 2 0.348083 0.667589 0.465276 11.00000 -1.20000 AFIX 0 C2 1 0.483575 0.663418 0.435705 11.00000 0.04514 0.05317 = 0.11835 -0.00428 0.00214 -0.01062 AFIX 43 H2 2 0.498909 0.699874 0.447583 11.00000 -1.20000 AFIX 0 C3 1 0.551055 0.628962 0.409346 11.00000 0.03286 0.06600 = 0.10059 0.00468 0.00624 -0.01291 AFIX 43 H3 2 0.613899 0.641393 0.404824 11.00000 -1.20000 AFIX 0 C4 1 0.527094 0.576826 0.389749 11.00000 0.02955 0.06439 = 0.06821 0.00389 0.00621 0.00107 AFIX 43 H4 2 0.573033 0.552975 0.371208 11.00000 -1.20000 AFIX 0 C5 1 0.434986 0.559050 0.397196 11.00000 0.02708 0.05526 = 0.04724 0.00409 0.00129 0.00348 C6 1 0.401137 0.505003 0.377130 11.00000 0.02636 0.05113 = 0.04459 0.00452 0.00085 0.00494 C7 1 0.454075 0.461065 0.359166 11.00000 0.03148 0.06180 = 0.04643 0.00410 0.00382 0.00931 AFIX 43 H7 2 0.521154 0.464193 0.357897 11.00000 -1.20000 AFIX 0 C8 1 0.408020 0.412131 0.342936 11.00000 0.04608 0.05145 = 0.06358 -0.00150 0.00392 0.01034 AFIX 43 H8 2 0.443444 0.381817 0.328841 11.00000 -1.20000 AFIX 0 C9 1 0.310588 0.407402 0.347245 11.00000 0.04932 0.04802 = 0.05394 0.00570 -0.00101 0.00089 AFIX 43 H9 2 0.279426 0.373847 0.337403 11.00000 -1.20000 AFIX 0 C10 1 0.259806 0.451445 0.365774 11.00000 0.03112 0.05057 = 0.04435 0.00542 0.00030 0.00016 C11 1 0.156256 0.455426 0.373198 11.00000 0.03188 0.05657 = 0.04413 0.00335 -0.00291 -0.00372 C12 1 0.094156 0.412284 0.363525 11.00000 0.04370 0.06310 = 0.05321 0.00712 -0.00550 -0.00870 AFIX 43 H12 2 0.117604 0.377698 0.353297 11.00000 -1.20000 AFIX 0 C13 1 -0.002274 0.419836 0.368842 11.00000 0.03967 0.08611 = 0.05591 0.00854 -0.00769 -0.02224 AFIX 43 H13 2 -0.045106 0.390410 0.364983 11.00000 -1.20000 AFIX 0 C14 1 -0.034950 0.470314 0.379737 11.00000 0.02748 0.09336 = 0.05960 0.00076 0.00045 -0.00802 AFIX 43 H14 2 -0.101572 0.476580 0.379642 11.00000 -1.20000 AFIX 0 C15 1 0.029417 0.511877 0.390820 11.00000 0.02513 0.07724 = 0.05277 0.00587 -0.00129 0.00160 AFIX 43 H15 2 0.005959 0.546798 0.398075 11.00000 -1.20000 AFIX 0 C16 1 0.127867 0.658339 0.393422 11.00000 0.03186 0.05588 = 0.05563 0.00118 0.00311 0.00648 C17 1 0.151903 0.645443 0.295662 11.00000 0.02848 0.04936 = 0.05612 0.00081 0.00471 0.00434 C18 1 0.131750 0.678760 0.216280 11.00000 0.03371 0.04943 = 0.06035 0.00418 0.00214 0.00354 AFIX 43 H18 2 0.101951 0.712208 0.222183 11.00000 -1.20000 AFIX 0 C19 1 0.154863 0.663477 0.128587 11.00000 0.03141 0.04815 = 0.05735 0.00627 0.00357 0.00119 C20 1 0.194527 0.613427 0.121256 11.00000 0.03282 0.05239 = 0.05154 -0.00134 0.00323 0.00247 AFIX 43 H20 2 0.208020 0.601150 0.060555 11.00000 -1.20000 AFIX 0 C21 1 0.214287 0.581461 0.203779 11.00000 0.03036 0.04400 = 0.05318 0.00136 0.00038 0.00309 AFIX 43 H21 2 0.242491 0.547488 0.198725 11.00000 -1.20000 AFIX 0 CL1 3 0.279583 0.528991 0.583486 11.00000 0.02837 0.06461 = 0.05285 0.00662 0.00115 0.00220 N1 4 0.368338 0.593270 0.424727 11.00000 0.02782 0.04871 = 0.05477 -0.00093 -0.00093 0.00291 N2 4 0.304700 0.499597 0.379403 11.00000 0.02593 0.05141 = 0.04178 0.00606 -0.00068 0.00363 N3 4 0.125150 0.504904 0.391786 11.00000 0.02449 0.06005 = 0.04966 0.00635 0.00184 -0.00018 N4 4 0.194750 0.597123 0.290246 11.00000 0.02716 0.04626 = 0.05023 0.00161 0.00163 0.00277 O1 5 0.155355 0.624898 0.460373 11.00000 0.03687 0.05857 = 0.05436 -0.00079 0.00442 0.01538 O2 5 0.081192 0.699960 0.402226 11.00000 0.04583 0.05771 = 0.06482 0.00021 0.01001 0.01678 O3 5 0.199114 0.692457 -0.045818 11.00000 0.04775 0.05293 = 0.06561 0.00210 0.01394 -0.00914 O4 5 0.148209 0.763513 0.065450 11.00000 0.04794 0.05115 = 0.07744 0.00563 0.01887 -0.00305 H4A 2 0.205443 0.777263 0.057608 11.00000 -1.50000 O5 5 0.026616 0.700990 -0.024167 11.00000 0.04167 0.06011 = 0.06529 0.01467 0.00465 -0.00743 H5 2 -0.022835 0.708097 0.024342 11.00000 -1.50000 P1 6 0.133152 0.707079 0.023211 11.00000 0.03991 0.04831 = 0.05947 0.00673 0.00989 -0.00419 RU1 7 0.234637 0.559479 0.418788 11.00000 0.02286 0.04811 = 0.04922 0.00303 0.00027 0.00474 HKLF 4 REM janb0402_a.res in C2/c REM wR2 = 0.1444, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0518 for 4067 Fo > 4sig(Fo) and 0.0623 for all 4949 data REM 304 parameters refined using 0 restraints END WGHT 0.1027 1.9077 REM Highest difference peak 2.404, deepest hole -0.601, 1-sigma level 0.157 Q1 1 0.2425 0.5428 0.3632 11.00000 0.05 2.40 Q2 1 0.2381 0.5992 0.3936 11.00000 0.05 1.28 Q3 1 0.2229 0.5183 0.4365 11.00000 0.05 0.78 Q4 1 0.1826 0.5581 0.4672 11.00000 0.05 0.68 Q5 1 0.2640 0.5589 0.5252 11.00000 0.05 0.63 Q6 1 0.2656 0.5634 0.5500 11.00000 0.05 0.62 Q7 1 0.3887 0.5733 0.3785 11.00000 0.05 0.55 Q8 1 0.2794 0.4867 0.3632 11.00000 0.05 0.55 Q9 1 0.3344 0.4997 0.3825 11.00000 0.05 0.49 Q10 1 0.1415 0.6798 0.0971 11.00000 0.05 0.48 Q11 1 0.2774 0.5642 0.6178 11.00000 0.05 0.47 Q12 1 0.4172 0.4610 0.3486 11.00000 0.05 0.44 Q13 1 0.1459 0.4995 0.3476 11.00000 0.05 0.44 Q14 1 0.1625 0.6183 0.3350 11.00000 0.05 0.44 Q15 1 0.4386 0.5430 0.3761 11.00000 0.05 0.42 Q16 1 0.2170 0.6021 0.1756 11.00000 0.05 0.41 Q17 1 0.2773 0.4412 0.3286 11.00000 0.05 0.40 Q18 1 0.2422 0.5079 0.6227 11.00000 0.05 0.39 Q19 1 -0.0115 0.4615 0.3456 11.00000 0.05 0.38 Q20 1 0.2223 0.4628 0.3638 11.00000 0.05 0.38 Q21 1 0.1393 0.6600 0.3403 11.00000 0.05 0.37 Q22 1 0.2775 0.4777 0.5995 11.00000 0.05 0.37 Q23 1 0.2415 0.5347 0.6306 11.00000 0.05 0.37 Q24 1 0.3691 0.6177 0.3940 11.00000 0.05 0.36 Q25 1 0.1544 0.7131 0.1060 11.00000 0.05 0.34 Q26 1 0.1315 0.6826 -0.0425 11.00000 0.05 0.34 Q27 1 0.1315 0.7821 0.1189 11.00000 0.05 0.33 Q28 1 0.1203 0.6660 0.1580 11.00000 0.05 0.33 Q29 1 0.5140 0.5998 0.3613 11.00000 0.05 0.32 Q30 1 0.4972 0.5643 0.3600 11.00000 0.05 0.31 ; _shelx_res_checksum 34914 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 C1 C 0.3935(3) 0.6442(2) 0.4446(4) 0.0579(12) Uani 1 1 d . . . . . H1 H 0.348083 0.667589 0.465276 0.069 Uiso 1 1 calc R U . . . C2 C 0.4836(4) 0.6634(2) 0.4357(5) 0.0737(16) Uani 1 1 d . . . . . H2 H 0.498909 0.699874 0.447583 0.088 Uiso 1 1 calc R U . . . C3 C 0.5511(3) 0.6290(2) 0.4093(5) 0.0671(14) Uani 1 1 d . . . . . H3 H 0.613899 0.641393 0.404824 0.081 Uiso 1 1 calc R U . . . C4 C 0.5271(3) 0.5768(2) 0.3897(4) 0.0543(11) Uani 1 1 d . . . . . H4 H 0.573033 0.552975 0.371208 0.065 Uiso 1 1 calc R U . . . C5 C 0.4350(3) 0.55905(17) 0.3972(3) 0.0438(9) Uani 1 1 d . . . . . C6 C 0.4011(3) 0.50500(17) 0.3771(3) 0.0413(8) Uani 1 1 d . . . . . C7 C 0.4541(3) 0.46106(19) 0.3592(3) 0.0469(9) Uani 1 1 d . . . . . H7 H 0.521154 0.464193 0.357897 0.056 Uiso 1 1 calc R U . . . C8 C 0.4080(3) 0.4121(2) 0.3429(4) 0.0544(11) Uani 1 1 d . . . . . H8 H 0.443444 0.381817 0.328841 0.065 Uiso 1 1 calc R U . . . C9 C 0.3106(3) 0.40740(19) 0.3472(3) 0.0516(10) Uani 1 1 d . . . . . H9 H 0.279426 0.373847 0.337403 0.062 Uiso 1 1 calc R U . . . C10 C 0.2598(3) 0.45144(17) 0.3658(3) 0.0428(9) Uani 1 1 d . . . . . C11 C 0.1563(3) 0.45543(19) 0.3732(3) 0.0453(9) Uani 1 1 d . . . . . C12 C 0.0942(3) 0.4123(2) 0.3635(4) 0.0550(11) Uani 1 1 d . . . . . H12 H 0.117604 0.377698 0.353297 0.066 Uiso 1 1 calc R U . . . C13 C -0.0023(3) 0.4198(3) 0.3688(4) 0.0625(14) Uani 1 1 d . . . . . H13 H -0.045106 0.390410 0.364983 0.075 Uiso 1 1 calc R U . . . C14 C -0.0349(3) 0.4703(2) 0.3797(4) 0.0610(13) Uani 1 1 d . . . . . H14 H -0.101572 0.476580 0.379642 0.073 Uiso 1 1 calc R U . . . C15 C 0.0294(3) 0.5119(2) 0.3908(3) 0.0527(11) Uani 1 1 d . . . . . H15 H 0.005959 0.546798 0.398075 0.063 Uiso 1 1 calc R U . . . C16 C 0.1279(3) 0.65834(19) 0.3934(3) 0.0483(10) Uani 1 1 d . . . . . C17 C 0.1519(3) 0.64544(18) 0.2957(3) 0.0450(9) Uani 1 1 d . . . . . C18 C 0.1317(3) 0.67876(19) 0.2163(3) 0.0486(10) Uani 1 1 d . . . . . H18 H 0.101951 0.712208 0.222183 0.058 Uiso 1 1 calc R U . . . C19 C 0.1549(3) 0.66348(18) 0.1286(3) 0.0461(9) Uani 1 1 d . . . . . C20 C 0.1945(3) 0.61343(18) 0.1213(3) 0.0461(9) Uani 1 1 d . . . . . H20 H 0.208020 0.601150 0.060555 0.055 Uiso 1 1 calc R U . . . C21 C 0.2143(3) 0.58146(17) 0.2038(3) 0.0433(9) Uani 1 1 d . . . . . H21 H 0.242491 0.547488 0.198725 0.052 Uiso 1 1 calc R U . . . Cl1 Cl 0.27958(7) 0.52899(5) 0.58349(8) 0.0493(3) Uani 1 1 d . . . . . N1 N 0.3683(2) 0.59327(15) 0.4247(3) 0.0447(8) Uani 1 1 d . . . . . N2 N 0.3047(2) 0.49960(15) 0.3794(2) 0.0405(7) Uani 1 1 d . . . . . N3 N 0.1252(2) 0.50490(16) 0.3918(3) 0.0453(8) Uani 1 1 d . . . . . N4 N 0.1948(2) 0.59712(14) 0.2902(3) 0.0418(7) Uani 1 1 d . . . . . O1 O 0.1554(2) 0.62490(13) 0.4604(2) 0.0504(7) Uani 1 1 d . . . . . O2 O 0.0812(2) 0.69996(14) 0.4022(3) 0.0561(8) Uani 1 1 d . . . . . O3 O 0.1991(2) 0.69246(13) -0.0458(3) 0.0549(8) Uani 1 1 d . . . . . O4 O 0.1482(3) 0.76351(14) 0.0654(3) 0.0579(8) Uani 1 1 d . . . . . H4A H 0.205(6) 0.777(3) 0.058(5) 0.087 Uiso 1 1 d . U . . . O5 O 0.0266(2) 0.70099(14) -0.0242(3) 0.0563(8) Uani 1 1 d . . . . . H5 H -0.023(5) 0.708(3) 0.024(5) 0.084 Uiso 1 1 d . U . . . P1 P 0.13315(8) 0.70708(5) 0.02321(9) 0.0491(3) Uani 1 1 d . . . . . Ru1 Ru 0.23464(2) 0.55948(2) 0.41879(2) 0.04079(14) Uani 1 1 d . . . . . 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 C1 0.040(2) 0.053(3) 0.077(3) -0.007(2) -0.001(2) -0.0027(19) C2 0.045(3) 0.053(3) 0.118(5) -0.004(3) 0.002(3) -0.011(2) C3 0.033(2) 0.066(3) 0.101(4) 0.005(3) 0.006(2) -0.013(2) C4 0.0295(19) 0.064(3) 0.068(3) 0.004(2) 0.0062(19) 0.0011(19) C5 0.0271(18) 0.055(2) 0.047(2) 0.0041(18) 0.0013(16) 0.0035(16) C6 0.0264(16) 0.051(2) 0.045(2) 0.0045(17) 0.0009(15) 0.0049(15) C7 0.0315(18) 0.062(3) 0.046(2) 0.004(2) 0.0038(16) 0.0093(18) C8 0.046(2) 0.051(3) 0.064(3) -0.002(2) 0.004(2) 0.0103(19) C9 0.049(2) 0.048(2) 0.054(2) 0.006(2) -0.0010(19) 0.0009(19) C10 0.0311(19) 0.051(2) 0.044(2) 0.0054(17) 0.0003(16) 0.0002(16) C11 0.0319(19) 0.057(2) 0.044(2) 0.0034(19) -0.0029(16) -0.0037(17) C12 0.044(2) 0.063(3) 0.053(3) 0.007(2) -0.0055(19) -0.009(2) C13 0.040(2) 0.086(4) 0.056(3) 0.009(3) -0.008(2) -0.022(2) C14 0.0275(19) 0.093(4) 0.060(3) 0.001(3) 0.0004(18) -0.008(2) C15 0.0251(17) 0.077(3) 0.053(2) 0.006(2) -0.0013(16) 0.0016(19) C16 0.0319(18) 0.056(2) 0.056(3) 0.001(2) 0.0031(17) 0.0065(17) C17 0.0285(17) 0.049(2) 0.056(2) 0.0008(19) 0.0047(16) 0.0043(16) C18 0.0337(19) 0.049(2) 0.060(3) 0.004(2) 0.0021(18) 0.0035(17) C19 0.0314(18) 0.048(2) 0.057(2) 0.0063(19) 0.0036(17) 0.0012(16) C20 0.0328(18) 0.052(2) 0.052(2) -0.0013(19) 0.0032(16) 0.0025(17) C21 0.0304(18) 0.044(2) 0.053(2) 0.0014(18) 0.0004(16) 0.0031(16) Cl1 0.0284(4) 0.0646(7) 0.0528(6) 0.0066(5) 0.0012(4) 0.0022(4) N1 0.0278(15) 0.0487(19) 0.055(2) -0.0009(16) -0.0009(14) 0.0029(13) N2 0.0259(14) 0.0514(19) 0.0418(17) 0.0061(14) -0.0007(12) 0.0036(13) N3 0.0245(14) 0.060(2) 0.050(2) 0.0063(16) 0.0018(13) -0.0002(14) N4 0.0272(14) 0.0463(18) 0.0502(19) 0.0016(15) 0.0016(13) 0.0028(13) O1 0.0369(14) 0.0586(18) 0.0544(18) -0.0008(14) 0.0044(13) 0.0154(13) O2 0.0458(17) 0.0577(19) 0.065(2) 0.0002(15) 0.0100(15) 0.0168(14) O3 0.0477(17) 0.0529(18) 0.066(2) 0.0021(15) 0.0139(15) -0.0091(14) O4 0.0479(18) 0.0512(18) 0.077(2) 0.0056(16) 0.0189(17) -0.0030(14) O5 0.0417(16) 0.0601(19) 0.065(2) 0.0147(16) 0.0046(14) -0.0074(14) P1 0.0399(5) 0.0483(6) 0.0595(7) 0.0067(5) 0.0099(5) -0.0042(4) Ru1 0.02286(18) 0.0481(2) 0.0492(2) 0.00303(13) 0.00027(12) 0.00474(11) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ru Ru 0.0552 3.2960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 1 0 0.0106 0 -1 0 0.0026 -5 0 2 0.0716 5 0 -2 0.1016 -1 5 -4 0.0086 1 -1 5 0.0129 -1 -1 -5 0.0010 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 C2 C1 H1 119.1 . . ? N1 C1 H1 119.1 . . ? N1 C1 C2 121.9(5) . . ? C1 C2 H2 120.4 . . ? C3 C2 C1 119.2(5) . . ? C3 C2 H2 120.4 . . ? C2 C3 H3 120.1 . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C3 C4 H4 120.2 . . ? C3 C4 C5 119.5(5) . . ? C5 C4 H4 120.2 . . ? C4 C5 C6 124.4(4) . . ? N1 C5 C4 120.6(4) . . ? N1 C5 C6 115.0(3) . . ? C7 C6 C5 128.0(4) . . ? N2 C6 C5 112.4(4) . . ? N2 C6 C7 119.5(4) . . ? C6 C7 H7 120.4 . . ? C6 C7 C8 119.2(4) . . ? C8 C7 H7 120.4 . . ? C7 C8 H8 119.9 . . ? C9 C8 C7 120.3(4) . . ? C9 C8 H8 119.9 . . ? C8 C9 H9 120.3 . . ? C10 C9 C8 119.4(4) . . ? C10 C9 H9 120.3 . . ? C9 C10 C11 128.3(4) . . ? N2 C10 C9 120.1(4) . . ? N2 C10 C11 111.5(4) . . ? C12 C11 C10 123.5(4) . . ? N3 C11 C10 115.4(4) . . ? N3 C11 C12 121.2(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 C11 119.6(5) . . ? C13 C12 H12 120.2 . . ? C12 C13 H13 120.5 . . ? C14 C13 C12 119.0(5) . . ? C14 C13 H13 120.5 . . ? C13 C14 H14 120.3 . . ? C13 C14 C15 119.4(4) . . ? C15 C14 H14 120.3 . . ? C14 C15 H15 118.8 . . ? N3 C15 C14 122.4(5) . . ? N3 C15 H15 118.8 . . ? O1 C16 C17 116.0(4) . . ? O2 C16 C17 118.4(4) . . ? O2 C16 O1 125.5(4) . . ? C18 C17 C16 123.5(4) . . ? N4 C17 C16 114.6(4) . . ? N4 C17 C18 121.9(4) . . ? C17 C18 H18 120.1 . . ? C19 C18 C17 119.8(4) . . ? C19 C18 H18 120.1 . . ? C18 C19 C20 118.7(4) . . ? C18 C19 P1 121.2(3) . . ? C20 C19 P1 120.1(4) . . ? C19 C20 H20 120.4 . . ? C19 C20 C21 119.2(4) . . ? C21 C20 H20 120.4 . . ? C20 C21 H21 119.0 . . ? N4 C21 C20 122.0(4) . . ? N4 C21 H21 119.0 . . ? C1 N1 C5 119.1(4) . . ? C1 N1 Ru1 127.5(3) . . ? C5 N1 Ru1 113.2(3) . . ? C6 N2 Ru1 119.1(3) . . ? C10 N2 C6 121.4(4) . . ? C10 N2 Ru1 119.0(3) . . ? C11 N3 Ru1 113.1(3) . . ? C15 N3 C11 118.0(4) . . ? C15 N3 Ru1 129.0(3) . . ? C17 N4 Ru1 115.2(3) . . ? C21 N4 C17 118.2(4) . . ? C21 N4 Ru1 126.2(3) . . ? C16 O1 Ru1 114.9(3) . . ? P1 O4 H4A 112(5) . . ? P1 O5 H5 114(4) . . ? O3 P1 C19 109.6(2) . . ? O3 P1 O4 114.47(19) . . ? O3 P1 O5 111.6(2) . . ? O4 P1 C19 104.8(2) . . ? O5 P1 C19 107.52(18) . . ? O5 P1 O4 108.4(2) . . ? N1 Ru1 Cl1 90.41(10) . . ? N1 Ru1 O1 100.90(13) . . ? N2 Ru1 Cl1 87.70(10) . . ? N2 Ru1 N1 79.93(14) . . ? N2 Ru1 N3 80.19(14) . . ? N2 Ru1 N4 100.99(14) . . ? N2 Ru1 O1 178.98(13) . . ? N3 Ru1 Cl1 91.46(10) . . ? N3 Ru1 N1 159.93(15) . . ? N3 Ru1 O1 98.96(14) . . ? N4 Ru1 Cl1 170.45(11) . . ? N4 Ru1 N1 87.26(14) . . ? N4 Ru1 N3 93.90(14) . . ? N4 Ru1 O1 78.49(13) . . ? O1 Ru1 Cl1 92.87(9) . . ? 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 C1 H1 0.9500 . ? C1 C2 1.382(7) . ? C1 N1 1.345(6) . ? C2 H2 0.9500 . ? C2 C3 1.382(8) . ? C3 H3 0.9500 . ? C3 C4 1.370(8) . ? C4 H4 0.9500 . ? C4 C5 1.391(6) . ? C5 C6 1.452(6) . ? C5 N1 1.376(5) . ? C6 C7 1.380(6) . ? C6 N2 1.369(5) . ? C7 H7 0.9500 . ? C7 C8 1.391(7) . ? C8 H8 0.9500 . ? C8 C9 1.387(7) . ? C9 H9 0.9500 . ? C9 C10 1.367(7) . ? C10 C11 1.481(6) . ? C10 N2 1.364(6) . ? C11 C12 1.385(7) . ? C11 N3 1.359(6) . ? C12 H12 0.9500 . ? C12 C13 1.384(7) . ? C13 H13 0.9500 . ? C13 C14 1.368(9) . ? C14 H14 0.9500 . ? C14 C15 1.374(7) . ? C15 H15 0.9500 . ? C15 N3 1.356(5) . ? C16 C17 1.495(6) . ? C16 O1 1.265(5) . ? C16 O2 1.253(5) . ? C17 C18 1.377(6) . ? C17 N4 1.365(5) . ? C18 H18 0.9500 . ? C18 C19 1.373(7) . ? C19 C20 1.388(6) . ? C19 P1 1.815(5) . ? C20 H20 0.9500 . ? C20 C21 1.391(6) . ? C21 H21 0.9500 . ? C21 N4 1.341(6) . ? Cl1 Ru1 2.3970(11) . ? N1 Ru1 2.052(3) . ? N2 Ru1 1.931(4) . ? N3 Ru1 2.048(4) . ? N4 Ru1 2.017(4) . ? O1 Ru1 2.124(3) . ? O3 P1 1.494(3) . ? O4 H4A 0.90(8) . ? O4 P1 1.537(4) . ? O5 H5 1.07(7) . ? O5 P1 1.536(3) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C2 H2 O4 0.95 2.60 3.248(6) 125.9 8_566 yes C12 H12 O3 0.95 2.42 3.173(6) 136.3 6_566 yes O4 H4A O3 0.90(8) 1.58(8) 2.473(5) 174(7) 7_565 yes 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 C1 C2 C3 C4 1.8(10) . . . . ? C2 C1 N1 C5 1.7(8) . . . . ? C2 C1 N1 Ru1 -172.6(4) . . . . ? C2 C3 C4 C5 -0.4(9) . . . . ? C3 C4 C5 C6 179.2(5) . . . . ? C3 C4 C5 N1 -0.5(7) . . . . ? C4 C5 C6 C7 8.3(7) . . . . ? C4 C5 C6 N2 -173.1(4) . . . . ? C4 C5 N1 C1 -0.1(7) . . . . ? C4 C5 N1 Ru1 175.0(4) . . . . ? C5 C6 C7 C8 179.0(4) . . . . ? C5 C6 N2 C10 -177.7(4) . . . . ? C5 C6 N2 Ru1 -5.5(5) . . . . ? C6 C5 N1 C1 -179.9(4) . . . . ? C6 C5 N1 Ru1 -4.8(5) . . . . ? C6 C7 C8 C9 -1.6(7) . . . . ? C7 C6 N2 C10 1.0(6) . . . . ? C7 C6 N2 Ru1 173.2(3) . . . . ? C7 C8 C9 C10 1.2(7) . . . . ? C8 C9 C10 C11 179.8(4) . . . . ? C8 C9 C10 N2 0.3(7) . . . . ? C9 C10 C11 C12 1.3(7) . . . . ? C9 C10 C11 N3 -179.6(4) . . . . ? C9 C10 N2 C6 -1.5(6) . . . . ? C9 C10 N2 Ru1 -173.6(3) . . . . ? C10 C11 C12 C13 -178.2(4) . . . . ? C10 C11 N3 C15 174.3(4) . . . . ? C10 C11 N3 Ru1 -6.1(5) . . . . ? C11 C10 N2 C6 179.0(4) . . . . ? C11 C10 N2 Ru1 6.8(5) . . . . ? C11 C12 C13 C14 2.6(7) . . . . ? C12 C11 N3 C15 -6.6(6) . . . . ? C12 C11 N3 Ru1 173.1(3) . . . . ? C12 C13 C14 C15 -3.8(7) . . . . ? C13 C14 C15 N3 -0.2(7) . . . . ? C14 C15 N3 C11 5.4(7) . . . . ? C14 C15 N3 Ru1 -174.2(4) . . . . ? C16 C17 C18 C19 -178.9(4) . . . . ? C16 C17 N4 C21 176.8(3) . . . . ? C16 C17 N4 Ru1 -9.2(4) . . . . ? C17 C16 O1 Ru1 2.4(5) . . . . ? C17 C18 C19 C20 2.7(6) . . . . ? C17 C18 C19 P1 -178.0(3) . . . . ? C18 C17 N4 C21 -2.3(6) . . . . ? C18 C17 N4 Ru1 171.7(3) . . . . ? C18 C19 C20 C21 -3.3(6) . . . . ? C18 C19 P1 O3 156.3(3) . . . . ? C18 C19 P1 O4 33.0(4) . . . . ? C18 C19 P1 O5 -82.2(4) . . . . ? C19 C20 C21 N4 1.1(6) . . . . ? C20 C19 P1 O3 -24.4(4) . . . . ? C20 C19 P1 O4 -147.7(3) . . . . ? C20 C19 P1 O5 97.1(4) . . . . ? C20 C21 N4 C17 1.7(6) . . . . ? C20 C21 N4 Ru1 -171.6(3) . . . . ? N1 C1 C2 C3 -2.5(9) . . . . ? N1 C5 C6 C7 -172.0(4) . . . . ? N1 C5 C6 N2 6.6(5) . . . . ? N2 C6 C7 C8 0.5(6) . . . . ? N2 C10 C11 C12 -179.2(4) . . . . ? N2 C10 C11 N3 0.0(5) . . . . ? N3 C11 C12 C13 2.7(7) . . . . ? N4 C17 C18 C19 0.1(6) . . . . ? O1 C16 C17 C18 -176.6(4) . . . . ? O1 C16 C17 N4 4.3(6) . . . . ? O2 C16 C17 C18 4.9(7) . . . . ? O2 C16 C17 N4 -174.1(4) . . . . ? O2 C16 O1 Ru1 -179.3(4) . . . . ? P1 C19 C20 C21 177.4(3) . . . . ?