# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_twh11jp07_sad _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24.50 H28.50 Cl1.50 N4 O6 Ru' _chemical_formula_weight 629.26 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' 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9060(9) _cell_length_b 17.7086(17) _cell_length_c 17.0210(17) _cell_angle_alpha 90.00 _cell_angle_beta 91.073(4) _cell_angle_gamma 90.00 _cell_volume 2684.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9989 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 31.5 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.196 _exptl_crystal_size_mid 0.178 _exptl_crystal_size_min 0.120 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 0.779 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.687 _exptl_absorpt_correction_T_max 0.746 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1996) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 35996 _diffrn_reflns_av_R_equivalents 0.0285 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5246 _reflns_number_gt 4717 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-AXS,2003)' _computing_cell_refinement 'SAINT (Bruker-AXS,2003)' _computing_data_reduction 'SAINT and XPREP (Bruker-AXS,2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; WinGX (Farrugia, 1999) SHELXTL (Bruker, 2003) ORTEP-3 (Farrugia, 1997) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.04P)^2^+5P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5246 _refine_ls_number_parameters 375 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.1040 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 1.215 _refine_ls_restrained_S_all 1.215 _refine_ls_shift/su_max 0.013 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ru1 Ru 0.05024(3) 0.241744(14) 0.101768(15) 0.02251(10) Uani 1 1 d . . . N1 N -0.1612(3) 0.26805(16) 0.14072(15) 0.0259(6) Uani 1 1 d . . . N2 N 0.0213(3) 0.34073(16) 0.04015(16) 0.0270(6) Uani 1 1 d . A . N3 N -0.0340(3) 0.19445(16) 0.00202(16) 0.0256(6) Uani 1 1 d . A . O1 O 0.0755(3) 0.13880(13) 0.15896(14) 0.0315(5) Uani 1 1 d . . . O2 O 0.1379(3) 0.29981(13) 0.19714(13) 0.0291(5) Uani 1 1 d . . . C1 C -0.2624(4) 0.2237(2) 0.17602(19) 0.0325(8) Uani 1 1 d . . . H1A H -0.2361 0.1730 0.1881 0.039 Uiso 1 1 calc R A . C2 C -0.4046(4) 0.2497(3) 0.1954(2) 0.0416(10) Uani 1 1 d . . . H2A H -0.4732 0.2176 0.2214 0.050 Uiso 1 1 calc R . . C3 C -0.4441(5) 0.3228(3) 0.1761(2) 0.0467(11) Uani 1 1 d . . . H3A H -0.5411 0.3414 0.1879 0.056 Uiso 1 1 calc R A . C4 C -0.3411(5) 0.3688(2) 0.1395(2) 0.0406(9) Uani 1 1 d . . . H4A H -0.3668 0.4192 0.1255 0.049 Uiso 1 1 calc R . . C5 C -0.2006(4) 0.3404(2) 0.1234(2) 0.0310(8) Uani 1 1 d . . . C6 C -0.0770(4) 0.38848(19) 0.0897(2) 0.0336(8) Uani 1 1 d . A . H6A H -0.1214 0.4297 0.0576 0.040 Uiso 1 1 calc R . . H6B H -0.0167 0.4115 0.1330 0.040 Uiso 1 1 calc R . . C7 C -0.0513(4) 0.3257(2) -0.0388(2) 0.0310(8) Uani 1 1 d . . . H7A H -0.1512 0.3502 -0.0409 0.037 Uiso 1 1 calc R A . H7B H 0.0106 0.3489 -0.0801 0.037 Uiso 1 1 calc R . . C8 C -0.0698(4) 0.24327(19) -0.0562(2) 0.0260(7) Uani 1 1 d . A . C9 C -0.1229(5) 0.2188(2) -0.1293(2) 0.0371(9) Uani 1 1 d . . . H9A H -0.1469 0.2543 -0.1695 0.044 Uiso 1 1 calc R A . C10 C -0.1402(6) 0.1428(2) -0.1426(3) 0.0559(13) Uani 1 1 d . . . H10A H -0.1777 0.1250 -0.1919 0.067 Uiso 1 1 calc R . . C11 C -0.1017(6) 0.0923(2) -0.0828(3) 0.0576(13) Uani 1 1 d . . . H11A H -0.1115 0.0394 -0.0907 0.069 Uiso 1 1 calc R A . C12 C -0.0492(5) 0.1203(2) -0.0119(2) 0.0407(9) Uani 1 1 d . A . H12A H -0.0227 0.0857 0.0287 0.049 Uiso 1 1 calc R . . C13A C 0.1882(12) 0.3669(6) 0.0315(6) 0.030(3) Uiso 0.50 1 d P A 1 H13A H 0.1942 0.4028 -0.0129 0.036 Uiso 0.50 1 calc PR A 1 H13B H 0.2205 0.3939 0.0799 0.036 Uiso 0.50 1 calc PR A 1 N4A N 0.2570(9) 0.2352(5) 0.0527(5) 0.025(2) Uiso 0.50 1 d P A 1 C14A C 0.2935(10) 0.3027(6) 0.0177(5) 0.024(2) Uiso 0.50 1 d P A 1 C15A C 0.4254(11) 0.3119(6) -0.0246(5) 0.035(2) Uiso 0.50 1 d P A 1 H15A H 0.4487 0.3587 -0.0489 0.042 Uiso 0.50 1 calc PR A 1 C16A C 0.5197(10) 0.2514(7) -0.0300(6) 0.038(2) Uiso 0.50 1 d P A 1 H16A H 0.6107 0.2558 -0.0578 0.045 Uiso 0.50 1 calc PR A 1 C17A C 0.4827(10) 0.1836(6) 0.0051(5) 0.036(2) Uiso 0.50 1 d P A 1 H17A H 0.5479 0.1414 0.0014 0.043 Uiso 0.50 1 calc PR A 1 C18A C 0.3502(11) 0.1778(6) 0.0457(6) 0.032(2) Uiso 0.50 1 d P A 1 H18A H 0.3255 0.1310 0.0693 0.038 Uiso 0.50 1 calc PR A 1 C13B C 0.1619(11) 0.3787(6) 0.0341(6) 0.026(3) Uiso 0.50 1 d P A 2 H13C H 0.1870 0.4049 0.0840 0.031 Uiso 0.50 1 calc PR A 2 H13D H 0.1565 0.4168 -0.0085 0.031 Uiso 0.50 1 calc PR A 2 N4B N 0.2576(9) 0.2526(5) 0.0475(5) 0.023(2) Uiso 0.50 1 d P A 2 C14B C 0.2779(10) 0.3218(6) 0.0168(5) 0.026(3) Uiso 0.50 1 d P A 2 C15B C 0.4057(9) 0.3368(5) -0.0263(5) 0.0281(19) Uiso 0.50 1 d P A 2 H15B H 0.4193 0.3853 -0.0487 0.034 Uiso 0.50 1 calc PR A 2 C16B C 0.5139(10) 0.2810(6) -0.0368(5) 0.032(2) Uiso 0.50 1 d P A 2 H16B H 0.6012 0.2916 -0.0661 0.039 Uiso 0.50 1 calc PR A 2 C17B C 0.4940(9) 0.2110(6) -0.0047(5) 0.0270(17) Uiso 0.50 1 d P A 2 H17B H 0.5671 0.1725 -0.0111 0.032 Uiso 0.50 1 calc PR A 2 C18B C 0.3635(10) 0.1971(5) 0.0376(5) 0.026(2) Uiso 0.50 1 d P A 2 H18B H 0.3480 0.1486 0.0599 0.032 Uiso 0.50 1 calc PR A 2 C19 C 0.1402(6) 0.0521(2) 0.2592(3) 0.0507(11) Uani 1 1 d . A . H19A H 0.0379 0.0325 0.2640 0.076 Uiso 1 1 calc R . . H19B H 0.1902 0.0522 0.3109 0.076 Uiso 1 1 calc R . . H19C H 0.1965 0.0199 0.2233 0.076 Uiso 1 1 calc R . . C20 C 0.1342(4) 0.1318(2) 0.2272(2) 0.0321(8) Uani 1 1 d . . . C21 C 0.1916(4) 0.1903(2) 0.2742(2) 0.0329(8) Uani 1 1 d . A . H21A H 0.2376 0.1754 0.3226 0.039 Uiso 1 1 calc R . . C22 C 0.1896(4) 0.2678(2) 0.25890(19) 0.0297(7) Uani 1 1 d . . . C23 C 0.2536(5) 0.3214(2) 0.3205(2) 0.0402(9) Uani 1 1 d . A . H23A H 0.2328 0.3736 0.3047 0.060 Uiso 1 1 calc R . . H23B H 0.3623 0.3139 0.3255 0.060 Uiso 1 1 calc R . . H23C H 0.2069 0.3113 0.3711 0.060 Uiso 1 1 calc R . . Cl1 Cl 0.33498(11) 0.54462(5) 0.14632(6) 0.0391(2) Uani 1 1 d . . . O11 O 0.3177(4) 0.54257(17) 0.06168(18) 0.0527(8) Uani 1 1 d . B . O12A O 0.4942(8) 0.5357(5) 0.1618(5) 0.061(2) Uani 0.55 1 d P B 1 O13A O 0.2506(10) 0.4845(5) 0.1835(4) 0.0518(19) Uani 0.55 1 d P B 1 O14A O 0.2910(11) 0.6170(4) 0.1736(4) 0.0454(18) Uani 0.55 1 d P B 1 O12B O 0.312(2) 0.4725(11) 0.1801(11) 0.046(5) Uiso 0.25 1 d P B 2 O13B O 0.236(2) 0.5977(10) 0.1813(10) 0.048(5) Uiso 0.25 1 d P B 2 O15B O 0.484(2) 0.5644(11) 0.1761(12) 0.064(6) Uiso 0.25 1 d P B 2 O12C O 0.411(3) 0.4835(15) 0.1702(14) 0.090(7) Uiso 0.20 1 d P B 3 O13C O 0.176(3) 0.5265(13) 0.1641(13) 0.079(6) Uiso 0.20 1 d P B 3 O14C O 0.365(3) 0.6205(17) 0.1682(17) 0.081(10) Uiso 0.20 1 d P B 3 Cl50 Cl 0.7185(4) 0.0099(3) 0.0767(4) 0.0676(17) Uani 0.25 1 d PG C -1 Cl51 Cl 0.4250(4) -0.0294(3) 0.1348(3) 0.0499(11) Uani 0.25 1 d PG C -1 C50 C 0.5906(8) 0.0191(8) 0.1536(5) 0.031(4) Uiso 0.25 1 d PG C -1 H50A H 0.6375 -0.0003 0.2028 0.037 Uiso 0.25 1 calc PR C -1 H50B H 0.5676 0.0733 0.1615 0.037 Uiso 0.25 1 calc PR C -1 C61 C 0.679(2) 0.0163(10) 0.1084(11) 0.0384(16) Uiso 0.25 1 d P D -2 H61A H 0.6783 0.0118 0.1658 0.058 Uiso 0.25 1 calc PR D -2 H61B H 0.7023 0.0685 0.0939 0.058 Uiso 0.25 1 calc PR D -2 H61C H 0.7550 -0.0176 0.0872 0.058 Uiso 0.25 1 calc PR D -2 C62 C 0.521(2) -0.0056(9) 0.0739(10) 0.0384(16) Uiso 0.25 1 d P D -2 H62A H 0.4927 -0.0573 0.0901 0.046 Uiso 0.25 1 calc PR D -2 H62B H 0.4431 0.0301 0.0917 0.046 Uiso 0.25 1 calc PR D -2 C63 C 0.5369(16) -0.0015(10) -0.0079(10) 0.0384(16) Uiso 0.25 1 d P D -2 H63A H 0.6055 -0.0428 -0.0232 0.046 Uiso 0.25 1 calc PR D -2 H63B H 0.5888 0.0466 -0.0194 0.046 Uiso 0.25 1 calc PR D -2 C64 C 0.410(2) -0.0055(9) -0.0579(10) 0.0384(16) Uiso 0.25 1 d P D -2 H64A H 0.3466 0.0397 -0.0496 0.046 Uiso 0.25 1 calc PR D -2 H64B H 0.3499 -0.0505 -0.0439 0.046 Uiso 0.25 1 calc PR D -2 C65 C 0.447(2) -0.0100(11) -0.1381(10) 0.0384(16) Uiso 0.25 1 d P D -2 H65A H 0.4639 -0.0628 -0.1524 0.058 Uiso 0.25 1 calc PR D -2 H65B H 0.5379 0.0194 -0.1473 0.058 Uiso 0.25 1 calc PR D -2 H65C H 0.3637 0.0104 -0.1703 0.058 Uiso 0.25 1 calc PR D -2 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 0.02467(16) 0.02466(15) 0.01810(14) -0.00067(10) -0.00202(10) -0.00019(10) N1 0.0300(15) 0.0312(15) 0.0164(13) -0.0017(11) -0.0017(11) 0.0001(12) N2 0.0333(16) 0.0268(14) 0.0207(14) 0.0001(11) -0.0019(12) -0.0027(12) N3 0.0255(15) 0.0289(14) 0.0223(14) -0.0017(11) -0.0010(11) 0.0014(11) O1 0.0421(15) 0.0277(12) 0.0245(12) 0.0002(9) -0.0071(11) 0.0029(11) O2 0.0331(13) 0.0335(13) 0.0205(11) -0.0014(9) -0.0038(10) -0.0042(10) C1 0.034(2) 0.044(2) 0.0195(16) 0.0003(14) 0.0006(14) -0.0050(16) C2 0.028(2) 0.072(3) 0.0252(18) -0.0054(18) 0.0029(15) -0.0076(18) C3 0.033(2) 0.075(3) 0.032(2) -0.011(2) -0.0008(17) 0.012(2) C4 0.044(2) 0.049(2) 0.0285(19) -0.0074(16) -0.0027(17) 0.0154(19) C5 0.039(2) 0.0327(18) 0.0218(17) -0.0054(13) -0.0046(14) 0.0052(15) C6 0.048(2) 0.0261(17) 0.0263(18) -0.0012(13) -0.0001(16) 0.0032(16) C7 0.039(2) 0.0319(18) 0.0224(17) 0.0024(13) -0.0058(15) -0.0006(15) C8 0.0230(17) 0.0333(18) 0.0217(16) -0.0009(13) -0.0024(13) 0.0020(13) C9 0.046(2) 0.041(2) 0.0237(18) -0.0010(15) -0.0094(16) 0.0032(17) C10 0.090(4) 0.042(2) 0.034(2) -0.0110(18) -0.026(2) 0.003(2) C11 0.096(4) 0.033(2) 0.043(2) -0.0083(18) -0.027(2) 0.002(2) C12 0.061(3) 0.0292(19) 0.031(2) -0.0017(15) -0.0131(18) 0.0029(18) C19 0.079(3) 0.036(2) 0.037(2) 0.0039(17) -0.014(2) 0.010(2) C20 0.037(2) 0.0347(19) 0.0251(17) 0.0029(14) 0.0008(15) 0.0068(15) C21 0.036(2) 0.041(2) 0.0221(17) 0.0034(14) -0.0050(14) 0.0043(16) C22 0.0254(18) 0.044(2) 0.0199(16) -0.0039(14) 0.0025(13) -0.0033(15) C23 0.044(2) 0.050(2) 0.0265(19) -0.0040(16) -0.0065(16) -0.0120(18) Cl1 0.0461(6) 0.0280(4) 0.0429(5) -0.0039(4) -0.0028(4) 0.0034(4) O11 0.073(2) 0.0442(17) 0.0409(16) -0.0067(13) 0.0016(15) -0.0013(15) O12A 0.049(4) 0.060(5) 0.074(5) -0.005(4) -0.021(3) 0.027(4) O13A 0.056(5) 0.057(4) 0.042(4) -0.002(3) 0.001(4) -0.026(4) O14A 0.057(6) 0.029(3) 0.049(4) -0.019(3) -0.016(4) 0.015(4) Cl50 0.044(3) 0.071(3) 0.089(4) 0.041(3) 0.040(3) 0.010(2) Cl51 0.027(2) 0.051(2) 0.072(3) -0.027(2) 0.0084(19) -0.0068(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N3 2.025(3) . ? Ru1 N4A 2.040(8) . ? Ru1 N2 2.056(3) . ? Ru1 N1 2.061(3) . ? Ru1 O2 2.063(2) . ? Ru1 O1 2.077(2) . ? Ru1 N4B 2.089(8) . ? N1 C1 1.346(5) . ? N1 C5 1.360(5) . ? N2 C13B 1.427(10) . ? N2 C6 1.490(4) . ? N2 C7 1.505(4) . ? N2 C13A 1.567(11) . ? N3 C12 1.340(5) . ? N3 C8 1.349(4) . ? O1 C20 1.271(4) . ? O2 C22 1.272(4) . ? C1 C2 1.392(6) . ? C2 C3 1.380(6) . ? C3 C4 1.384(6) . ? C4 C5 1.381(5) . ? C5 C6 1.512(5) . ? C7 C8 1.497(5) . ? C8 C9 1.392(5) . ? C9 C10 1.373(6) . ? C10 C11 1.393(6) . ? C11 C12 1.378(5) . ? C13A C14A 1.494(13) . ? N4A C18A 1.319(13) . ? N4A C14A 1.377(12) . ? C14A C15A 1.399(13) . ? C15A C16A 1.365(14) . ? C16A C17A 1.382(13) . ? C17A C18A 1.382(13) . ? C13B C14B 1.476(13) . ? N4B C14B 1.346(12) . ? N4B C18B 1.375(12) . ? C14B C15B 1.390(12) . ? C15B C16B 1.394(12) . ? C16B C17B 1.367(13) . ? C17B C18B 1.401(12) . ? C19 C20 1.514(5) . ? C20 C21 1.399(5) . ? C21 C22 1.398(5) . ? C22 C23 1.517(5) . ? Cl1 O12C 1.34(2) . ? Cl1 O14C 1.42(3) . ? Cl1 O12B 1.42(2) . ? Cl1 O14A 1.420(5) . ? Cl1 O13B 1.429(18) . ? Cl1 O11 1.446(3) . ? Cl1 O12A 1.446(7) . ? Cl1 O15B 1.45(2) . ? Cl1 O13A 1.454(7) . ? Cl1 O13C 1.49(2) . ? Cl50 C50 1.7589 . ? Cl51 C50 1.7324 . ? C61 C62 1.56(3) . ? C62 C63 1.40(2) . ? C63 C64 1.41(2) . ? C64 C65 1.41(2) . ? 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 N3 Ru1 N4A 87.5(2) . . ? N3 Ru1 N2 83.34(11) . . ? N4A Ru1 N2 86.8(2) . . ? N3 Ru1 N1 92.12(11) . . ? N4A Ru1 N1 169.0(2) . . ? N2 Ru1 N1 82.24(11) . . ? N3 Ru1 O2 174.28(10) . . ? N4A Ru1 O2 91.1(2) . . ? N2 Ru1 O2 91.05(10) . . ? N1 Ru1 O2 88.21(10) . . ? N3 Ru1 O1 93.74(10) . . ? N4A Ru1 O1 93.0(2) . . ? N2 Ru1 O1 177.07(10) . . ? N1 Ru1 O1 98.01(11) . . ? O2 Ru1 O1 91.87(9) . . ? N3 Ru1 N4B 89.1(2) . . ? N4A Ru1 N4B 8.8(3) . . ? N2 Ru1 N4B 78.4(2) . . ? N1 Ru1 N4B 160.3(2) . . ? O2 Ru1 N4B 88.7(2) . . ? O1 Ru1 N4B 101.5(2) . . ? C1 N1 C5 118.3(3) . . ? C1 N1 Ru1 129.4(3) . . ? C5 N1 Ru1 112.1(2) . . ? C13B N2 C6 107.4(5) . . ? C13B N2 C7 112.4(4) . . ? C6 N2 C7 111.1(3) . . ? C13B N2 C13A 11.0(6) . . ? C6 N2 C13A 117.0(5) . . ? C7 N2 C13A 111.2(4) . . ? C13B N2 Ru1 109.7(4) . . ? C6 N2 Ru1 105.3(2) . . ? C7 N2 Ru1 110.6(2) . . ? C13A N2 Ru1 100.9(4) . . ? C12 N3 C8 118.4(3) . . ? C12 N3 Ru1 126.0(2) . . ? C8 N3 Ru1 115.4(2) . . ? C20 O1 Ru1 123.6(2) . . ? C22 O2 Ru1 123.6(2) . . ? N1 C1 C2 122.1(4) . . ? C3 C2 C1 118.9(4) . . ? C2 C3 C4 119.4(4) . . ? C5 C4 C3 119.0(4) . . ? N1 C5 C4 122.1(4) . . ? N1 C5 C6 115.2(3) . . ? C4 C5 C6 122.6(3) . . ? N2 C6 C5 109.6(3) . . ? C8 C7 N2 113.1(3) . . ? N3 C8 C9 121.9(3) . . ? N3 C8 C7 117.2(3) . . ? C9 C8 C7 120.9(3) . . ? C10 C9 C8 119.2(4) . . ? C9 C10 C11 118.9(4) . . ? C12 C11 C10 118.9(4) . . ? N3 C12 C11 122.6(4) . . ? C14A C13A N2 112.9(7) . . ? C18A N4A C14A 118.4(8) . . ? C18A N4A Ru1 130.9(7) . . ? C14A N4A Ru1 110.5(6) . . ? N4A C14A C15A 122.0(9) . . ? N4A C14A C13A 116.0(8) . . ? C15A C14A C13A 121.9(9) . . ? C16A C15A C14A 117.8(9) . . ? C15A C16A C17A 120.0(9) . . ? C18A C17A C16A 119.5(9) . . ? N4A C18A C17A 122.2(10) . . ? N2 C13B C14B 108.2(7) . . ? C14B N4B C18B 120.4(9) . . ? C14B N4B Ru1 112.5(6) . . ? C18B N4B Ru1 127.0(7) . . ? N4B C14B C15B 119.7(10) . . ? N4B C14B C13B 116.3(8) . . ? C15B C14B C13B 123.9(9) . . ? C14B C15B C16B 120.5(9) . . ? C17B C16B C15B 119.7(8) . . ? C16B C17B C18B 118.7(8) . . ? N4B C18B C17B 121.0(9) . . ? O1 C20 C21 126.2(3) . . ? O1 C20 C19 115.5(3) . . ? C21 C20 C19 118.3(3) . . ? C22 C21 C20 128.1(3) . . ? O2 C22 C21 126.5(3) . . ? O2 C22 C23 114.7(3) . . ? C21 C22 C23 118.8(3) . . ? O12C Cl1 O14C 126.6(16) . . ? O12C Cl1 O12B 39.1(11) . . ? O14C Cl1 O12B 140.8(14) . . ? O12C Cl1 O14A 140.6(11) . . ? O14C Cl1 O14A 27.4(10) . . ? O12B Cl1 O14A 129.5(8) . . ? O12C Cl1 O13B 136.1(13) . . ? O14C Cl1 O13B 51.9(11) . . ? O12B Cl1 O13B 109.1(10) . . ? O14A Cl1 O13B 25.0(6) . . ? O12C Cl1 O11 109.1(11) . . ? O14C Cl1 O11 107.5(12) . . ? O12B Cl1 O11 111.6(8) . . ? O14A Cl1 O11 108.9(3) . . ? O13B Cl1 O11 112.1(7) . . ? O12C Cl1 O12A 50.7(13) . . ? O14C Cl1 O12A 82.9(11) . . ? O12B Cl1 O12A 88.7(8) . . ? O14A Cl1 O12A 108.4(5) . . ? O13B Cl1 O12A 127.6(8) . . ? O11 Cl1 O12A 105.3(4) . . ? O12C Cl1 O15B 68.7(14) . . ? O14C Cl1 O15B 60.9(12) . . ? O12B Cl1 O15B 102.4(11) . . ? O14A Cl1 O15B 85.6(8) . . ? O13B Cl1 O15B 105.3(10) . . ? O11 Cl1 O15B 115.7(8) . . ? O12A Cl1 O15B 22.8(7) . . ? O12C Cl1 O13A 62.4(13) . . ? O14C Cl1 O13A 132.5(12) . . ? O12B Cl1 O13A 23.5(7) . . ? O14A Cl1 O13A 111.7(6) . . ? O13B Cl1 O13A 88.3(7) . . ? O11 Cl1 O13A 111.7(3) . . ? O12A Cl1 O13A 110.7(5) . . ? O15B Cl1 O13A 120.0(9) . . ? O12C Cl1 O13C 104.0(16) . . ? O14C Cl1 O13C 109.1(14) . . ? O12B Cl1 O13C 64.9(11) . . ? O14A Cl1 O13C 81.9(10) . . ? O13B Cl1 O13C 57.2(10) . . ? O11 Cl1 O13C 96.5(9) . . ? O12A Cl1 O13C 150.8(10) . . ? O15B Cl1 O13C 147.8(12) . . ? O13A Cl1 O13C 41.7(9) . . ? Cl51 C50 Cl50 112.1 . . ? C63 C62 C61 104.6(15) . . ? C62 C63 C64 120.1(12) . . ? C63 C64 C65 112.9(17) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.048 _refine_diff_density_min -0.697 _refine_diff_density_rms 0.089 _database_code_depnum_ccdc_archive 'CCDC 941516' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_twh11jp08 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H31 Cl3 N4 O6 Ru' _chemical_formula_weight 799.05 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' 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 23.297(2) _cell_length_b 12.4626(12) _cell_length_c 25.803(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.977(4) _cell_angle_gamma 90.00 _cell_volume 6734.8(11) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9582 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 36.1 _exptl_crystal_description plate _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.526 _exptl_crystal_size_mid 0.373 _exptl_crystal_size_min 0.090 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3248 _exptl_absorpt_coefficient_mu 0.755 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6705 _exptl_absorpt_correction_T_max 0.7471 _exptl_absorpt_process_details ; SADABS (Sheldrick, 1996) ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 102834 _diffrn_reflns_av_R_equivalents 0.0238 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 36.27 _reflns_number_total 16222 _reflns_number_gt 13519 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-AXS,2003)' _computing_cell_refinement 'SAINT (Bruker-AXS,2003)' _computing_data_reduction 'SAINT and XPREP (Bruker-AXS,2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; WinGX (Farrugia, 1999) SHELXTL (Bruker, 2003) ORTEP-3 (Farrugia, 1997) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0340P)^2^+6.8000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16222 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0793 _refine_ls_wR_factor_gt 0.0717 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.22958(6) 0.28589(11) 0.16555(6) 0.0290(2) Uani 1 1 d . . . H1 H 0.2636 0.2377 0.1861 0.035 Uiso 1 1 calc R . . C2 C 0.16874(8) 0.24474(13) 0.13538(8) 0.0424(4) Uani 1 1 d . . . H2 H 0.1610 0.1701 0.1362 0.051 Uiso 1 1 calc R . . C3 C 0.11909(8) 0.31453(15) 0.10388(10) 0.0509(5) Uani 1 1 d . . . H3 H 0.0768 0.2883 0.0829 0.061 Uiso 1 1 calc R . . C4 C 0.13222(7) 0.42338(14) 0.10359(8) 0.0423(4) Uani 1 1 d . . . H4 H 0.0992 0.4721 0.0814 0.051 Uiso 1 1 calc R . . C5 C 0.19409(6) 0.46023(10) 0.13611(6) 0.0259(2) Uani 1 1 d . . . C6 C 0.20983(6) 0.57883(10) 0.14307(5) 0.0244(2) Uani 1 1 d . . . H6A H 0.1841 0.6163 0.1063 0.029 Uiso 1 1 calc R . . H6B H 0.1986 0.6092 0.1729 0.029 Uiso 1 1 calc R . . C7 C 0.29253(8) 0.59867(14) 0.10802(6) 0.0357(3) Uani 1 1 d . . . H7A H 0.2516 0.5898 0.0731 0.043 Uiso 1 1 calc R . . H7B H 0.3104 0.6695 0.1055 0.043 Uiso 1 1 calc R . . C8 C 0.33796(5) 0.51249(10) 0.10879(5) 0.0222(2) Uani 1 1 d . . . C9 C 0.35640(7) 0.50313(13) 0.06440(6) 0.0293(2) Uani 1 1 d . . . H9 H 0.3425 0.5541 0.0340 0.035 Uiso 1 1 calc R . . C10 C 0.39545(8) 0.41789(14) 0.06533(7) 0.0375(3) Uani 1 1 d . . . H10 H 0.4077 0.4088 0.0350 0.045 Uiso 1 1 calc R . . C11 C 0.41634(8) 0.34619(14) 0.11124(7) 0.0371(3) Uani 1 1 d . . . H11 H 0.4430 0.2874 0.1127 0.044 Uiso 1 1 calc R . . C12 C 0.39771(6) 0.36194(11) 0.15475(6) 0.0280(2) Uani 1 1 d . . . H12 H 0.4128 0.3138 0.1865 0.034 Uiso 1 1 calc R . . C13 C 0.30403(6) 0.69642(10) 0.19602(7) 0.0301(3) Uani 1 1 d . . . H13A H 0.2789 0.7099 0.2179 0.036 Uiso 1 1 calc R . . H13B H 0.2983 0.7586 0.1704 0.036 Uiso 1 1 calc R . . C14 C 0.37426(6) 0.68606(10) 0.23793(6) 0.0273(2) Uani 1 1 d . . . C15 C 0.41276(8) 0.77462(12) 0.26175(8) 0.0386(3) Uani 1 1 d . . . H15 H 0.3972 0.8448 0.2488 0.046 Uiso 1 1 calc R . . C16 C 0.47448(8) 0.75987(13) 0.30491(8) 0.0421(4) Uani 1 1 d . . . H16 H 0.5012 0.8198 0.3224 0.051 Uiso 1 1 calc R . . C17 C 0.49627(7) 0.65661(13) 0.32192(7) 0.0362(3) Uani 1 1 d . . . H17 H 0.5382 0.6445 0.3513 0.043 Uiso 1 1 calc R . . C18 C 0.45624(6) 0.57120(11) 0.29552(6) 0.0277(2) Uani 1 1 d . . . H18 H 0.4718 0.5003 0.3066 0.033 Uiso 1 1 calc R . . C19 C 0.44569(6) 0.16475(10) 0.31559(6) 0.0281(2) Uani 1 1 d . . . H19 H 0.4322 0.1749 0.2755 0.034 Uiso 1 1 calc R . . C20 C 0.48864(7) 0.08279(12) 0.34438(7) 0.0358(3) Uani 1 1 d . . . H20 H 0.5032 0.0362 0.3235 0.043 Uiso 1 1 calc R . . C21 C 0.51018(7) 0.06884(12) 0.40334(7) 0.0351(3) Uani 1 1 d . . . H21 H 0.5400 0.0138 0.4230 0.042 Uiso 1 1 calc R . . C22 C 0.48774(7) 0.13595(12) 0.43314(7) 0.0331(3) Uani 1 1 d . . . H22 H 0.5026 0.1269 0.4735 0.040 Uiso 1 1 calc R . . C23 C 0.44357(6) 0.21678(11) 0.40457(6) 0.0256(2) Uani 1 1 d . . . H23 H 0.4280 0.2614 0.4254 0.031 Uiso 1 1 calc R . . C24 C 0.42227(5) 0.23217(8) 0.34534(5) 0.01885(18) Uani 1 1 d . . . C25 C 0.37683(5) 0.31985(8) 0.31263(5) 0.01782(17) Uani 1 1 d . . . C26 C 0.33613(5) 0.36351(9) 0.33460(5) 0.01941(18) Uani 1 1 d . . . H26 H 0.3378 0.3309 0.3685 0.023 Uiso 1 1 calc R . . C27 C 0.29331(5) 0.44996(8) 0.31206(5) 0.01754(17) Uani 1 1 d . . . C28 C 0.24975(5) 0.47684(8) 0.33902(5) 0.01836(17) Uani 1 1 d . . . C29 C 0.26449(6) 0.45115(11) 0.39632(5) 0.0247(2) Uani 1 1 d . . . H29 H 0.3046 0.4198 0.4202 0.030 Uiso 1 1 calc R . . C30 C 0.22078(7) 0.47122(13) 0.41857(6) 0.0323(3) Uani 1 1 d . . . H30 H 0.2311 0.4524 0.4573 0.039 Uiso 1 1 calc R . . C31 C 0.16231(7) 0.51859(14) 0.38447(7) 0.0344(3) Uani 1 1 d . . . H31 H 0.1326 0.5324 0.3998 0.041 Uiso 1 1 calc R . . C32 C 0.14755(7) 0.54560(13) 0.32784(7) 0.0330(3) Uani 1 1 d . . . H32 H 0.1077 0.5783 0.3044 0.040 Uiso 1 1 calc R . . C33 C 0.19085(6) 0.52510(10) 0.30501(6) 0.0254(2) Uani 1 1 d . . . H33 H 0.1803 0.5440 0.2662 0.030 Uiso 1 1 calc R . . N1 N 0.24256(5) 0.39163(8) 0.16694(4) 0.02217(17) Uani 1 1 d . . . N2 N 0.27957(5) 0.59730(8) 0.16025(4) 0.02081(17) Uani 1 1 d . . . N3 N 0.35883(5) 0.44326(8) 0.15386(4) 0.02048(16) Uani 1 1 d . . . N4 N 0.39589(5) 0.58469(8) 0.25466(4) 0.02231(17) Uani 1 1 d . . . O1 O 0.37818(4) 0.34628(7) 0.26537(4) 0.02140(15) Uani 1 1 d . . . O2 O 0.28642(4) 0.50879(7) 0.26895(4) 0.02099(15) Uani 1 1 d . . . O11 O 0.37745(7) 0.78084(11) 0.07648(5) 0.0435(3) Uani 1 1 d . . . O12 O 0.45548(6) 0.79679(14) 0.04309(7) 0.0539(4) Uani 1 1 d . . . O13 O 0.35515(8) 0.72681(11) -0.01844(6) 0.0543(4) Uani 1 1 d . . . O14 O 0.36557(6) 0.90896(9) 0.00559(5) 0.0391(2) Uani 1 1 d . . . Cl1 Cl 0.387702(15) 0.80284(2) 0.026729(13) 0.02545(5) Uani 1 1 d . . . Ru1 Ru 0.326596(4) 0.471539(7) 0.214061(4) 0.01773(2) Uani 1 1 d . . . Cl40 Cl 0.44768(9) 0.48273(12) -0.06580(7) 0.0480(3) Uani 0.50 1 d P A -1 Cl41 Cl 0.54084(13) 0.5313(2) 0.04891(9) 0.0851(8) Uani 0.50 1 d P A -1 C40 C 0.48820(19) 0.5668(3) 0.0056(2) 0.0529(10) Uani 0.50 1 d P A -1 H40A H 0.4978 0.6387 -0.0049 0.063 Uiso 0.50 1 calc PR A -1 H40B H 0.4559 0.5771 0.0205 0.063 Uiso 0.50 1 calc PR A -1 Cl51 Cl 0.19442(6) 0.34432(9) 0.01316(5) 0.0528(2) Uani 0.50 1 d P B -1 C50 C 0.2468(2) 0.2344(4) 0.0313(2) 0.0524(10) Uani 0.50 1 d P B -1 H50A H 0.2842 0.2492 0.0685 0.063 Uiso 0.50 1 calc PR B -1 H50B H 0.2248 0.1702 0.0365 0.063 Uiso 0.50 1 calc PR B -1 Cl50 Cl 0.27343(8) 0.20706(15) -0.02111(7) 0.0735(4) Uani 0.50 1 d P B -1 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 0.0256(5) 0.0250(5) 0.0318(6) 0.0057(5) 0.0084(5) 0.0033(4) C2 0.0315(7) 0.0307(7) 0.0528(10) 0.0089(6) 0.0073(7) -0.0031(5) C3 0.0252(6) 0.0407(8) 0.0666(12) 0.0139(8) 0.0014(7) -0.0049(6) C4 0.0208(6) 0.0362(7) 0.0542(10) 0.0140(7) 0.0021(6) 0.0037(5) C5 0.0203(5) 0.0273(5) 0.0266(5) 0.0078(4) 0.0070(4) 0.0057(4) C6 0.0190(4) 0.0260(5) 0.0252(5) 0.0077(4) 0.0068(4) 0.0082(4) C7 0.0403(7) 0.0458(8) 0.0296(6) 0.0196(6) 0.0231(6) 0.0215(6) C8 0.0186(4) 0.0294(5) 0.0183(4) 0.0014(4) 0.0076(4) 0.0009(4) C9 0.0276(6) 0.0410(7) 0.0224(5) -0.0004(5) 0.0138(5) -0.0022(5) C10 0.0397(7) 0.0480(8) 0.0354(7) -0.0063(6) 0.0263(6) -0.0003(6) C11 0.0369(7) 0.0413(8) 0.0423(8) -0.0042(6) 0.0259(7) 0.0075(6) C12 0.0255(5) 0.0302(6) 0.0304(6) 0.0005(5) 0.0142(5) 0.0075(4) C13 0.0262(6) 0.0215(5) 0.0354(7) 0.0031(5) 0.0070(5) 0.0067(4) C14 0.0260(5) 0.0241(5) 0.0276(6) 0.0036(4) 0.0080(5) 0.0040(4) C15 0.0353(7) 0.0250(6) 0.0445(8) 0.0004(6) 0.0072(6) 0.0005(5) C16 0.0370(8) 0.0322(7) 0.0432(9) -0.0036(6) 0.0047(7) -0.0050(6) C17 0.0279(6) 0.0374(7) 0.0309(7) -0.0007(5) 0.0015(5) 0.0000(5) C18 0.0247(5) 0.0302(6) 0.0226(5) 0.0021(4) 0.0053(4) 0.0048(4) C19 0.0277(6) 0.0226(5) 0.0271(6) -0.0015(4) 0.0057(5) 0.0084(4) C20 0.0328(7) 0.0258(6) 0.0450(8) 0.0031(5) 0.0134(6) 0.0135(5) C21 0.0239(6) 0.0291(6) 0.0502(9) 0.0187(6) 0.0143(6) 0.0123(5) C22 0.0251(6) 0.0382(7) 0.0339(7) 0.0207(6) 0.0109(5) 0.0107(5) C23 0.0227(5) 0.0287(5) 0.0250(5) 0.0110(4) 0.0102(4) 0.0075(4) C24 0.0149(4) 0.0157(4) 0.0222(5) 0.0028(3) 0.0047(4) 0.0016(3) C25 0.0160(4) 0.0159(4) 0.0178(4) 0.0016(3) 0.0040(3) 0.0016(3) C26 0.0186(4) 0.0184(4) 0.0202(4) 0.0047(3) 0.0075(4) 0.0041(3) C27 0.0181(4) 0.0162(4) 0.0172(4) 0.0011(3) 0.0066(3) 0.0014(3) C28 0.0180(4) 0.0175(4) 0.0193(4) 0.0021(3) 0.0079(4) 0.0018(3) C29 0.0214(5) 0.0322(6) 0.0201(5) 0.0044(4) 0.0087(4) 0.0052(4) C30 0.0276(6) 0.0478(8) 0.0247(6) 0.0081(5) 0.0144(5) 0.0076(5) C31 0.0275(6) 0.0496(8) 0.0324(7) 0.0093(6) 0.0189(5) 0.0096(6) C32 0.0247(5) 0.0448(8) 0.0330(6) 0.0147(6) 0.0157(5) 0.0133(5) C33 0.0223(5) 0.0299(5) 0.0249(5) 0.0093(4) 0.0112(4) 0.0078(4) N1 0.0207(4) 0.0239(4) 0.0210(4) 0.0046(3) 0.0083(3) 0.0052(3) N2 0.0201(4) 0.0232(4) 0.0193(4) 0.0059(3) 0.0088(3) 0.0065(3) N3 0.0165(4) 0.0251(4) 0.0187(4) 0.0003(3) 0.0066(3) 0.0028(3) N4 0.0221(4) 0.0240(4) 0.0194(4) 0.0028(3) 0.0078(3) 0.0054(3) O1 0.0222(4) 0.0220(3) 0.0180(3) 0.0035(3) 0.0070(3) 0.0080(3) O2 0.0247(4) 0.0202(3) 0.0198(3) 0.0057(3) 0.0114(3) 0.0081(3) O11 0.0538(7) 0.0476(7) 0.0362(6) 0.0092(5) 0.0263(6) 0.0088(6) O12 0.0295(6) 0.0762(10) 0.0540(8) 0.0048(7) 0.0166(6) 0.0063(6) O13 0.0707(9) 0.0409(6) 0.0440(7) -0.0209(6) 0.0183(7) -0.0233(6) O14 0.0486(6) 0.0280(5) 0.0296(5) 0.0033(4) 0.0071(5) 0.0021(4) Cl1 0.02697(13) 0.02401(12) 0.02151(12) -0.00371(9) 0.00706(10) -0.00151(10) Ru1 0.01781(4) 0.01943(4) 0.01509(4) 0.00365(3) 0.00641(3) 0.00640(3) Cl40 0.0468(7) 0.0422(5) 0.0491(8) 0.0009(5) 0.0156(6) -0.0011(4) Cl41 0.0704(13) 0.1186(19) 0.0492(10) 0.0020(9) 0.0105(9) -0.0219(11) C40 0.0432(18) 0.0393(17) 0.079(3) 0.0170(18) 0.029(2) 0.0138(15) Cl51 0.0665(6) 0.0477(5) 0.0474(5) 0.0025(4) 0.0278(5) 0.0044(5) C50 0.058(3) 0.050(2) 0.050(2) -0.0026(19) 0.0233(19) -0.0014(19) Cl50 0.0789(9) 0.0838(10) 0.0802(9) -0.0329(8) 0.0554(8) -0.0179(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 1.3490(17) . ? C1 C2 1.383(2) . ? C2 C3 1.390(2) . ? C3 C4 1.391(2) . ? C4 C5 1.390(2) . ? C5 N1 1.3609(15) . ? C5 C6 1.5145(19) . ? C6 N2 1.5030(16) . ? C7 C8 1.5018(18) . ? C7 N2 1.5046(17) . ? C8 N3 1.3558(15) . ? C8 C9 1.3933(18) . ? C9 C10 1.392(2) . ? C10 C11 1.390(2) . ? C11 C12 1.384(2) . ? C12 N3 1.3527(16) . ? C13 N2 1.4972(17) . ? C13 C14 1.5211(19) . ? C14 N4 1.3586(16) . ? C14 C15 1.385(2) . ? C15 C16 1.392(2) . ? C16 C17 1.382(2) . ? C17 C18 1.382(2) . ? C18 N4 1.3482(16) . ? C19 C20 1.3946(18) . ? C19 C24 1.3999(17) . ? C20 C21 1.389(2) . ? C21 C22 1.384(2) . ? C22 C23 1.3974(17) . ? C23 C24 1.3980(17) . ? C24 C25 1.4982(14) . ? C25 O1 1.2768(14) . ? C25 C26 1.4099(16) . ? C26 C27 1.4091(15) . ? C27 O2 1.2822(13) . ? C27 C28 1.4981(16) . ? C28 C33 1.3999(16) . ? C28 C29 1.4007(16) . ? C29 C30 1.3932(18) . ? C30 C31 1.389(2) . ? C31 C32 1.388(2) . ? C32 C33 1.3965(18) . ? N1 Ru1 2.0537(11) . ? N2 Ru1 2.0621(9) . ? N3 Ru1 2.0305(10) . ? N4 Ru1 2.0520(11) . ? O1 Ru1 2.0592(8) . ? O2 Ru1 2.0637(8) . ? O11 Cl1 1.4313(12) . ? O12 Cl1 1.4467(13) . ? O13 Cl1 1.4342(12) . ? O14 Cl1 1.4375(11) . ? Cl40 C40 1.966(5) . ? Cl41 C40 1.322(5) . ? Cl51 C50 1.756(5) . ? C50 Cl50 1.751(5) . ? 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 C1 C2 122.67(12) . . ? C1 C2 C3 118.86(15) . . ? C2 C3 C4 118.99(15) . . ? C5 C4 C3 119.41(13) . . ? N1 C5 C4 121.39(12) . . ? N1 C5 C6 116.61(11) . . ? C4 C5 C6 121.81(11) . . ? N2 C6 C5 111.02(9) . . ? C8 C7 N2 113.37(10) . . ? N3 C8 C9 121.87(12) . . ? N3 C8 C7 116.89(10) . . ? C9 C8 C7 121.22(12) . . ? C10 C9 C8 118.96(13) . . ? C11 C10 C9 119.17(13) . . ? C12 C11 C10 118.88(14) . . ? N3 C12 C11 122.57(13) . . ? N2 C13 C14 111.63(10) . . ? N4 C14 C15 121.48(12) . . ? N4 C14 C13 116.02(11) . . ? C15 C14 C13 122.26(12) . . ? C14 C15 C16 119.40(14) . . ? C17 C16 C15 118.92(14) . . ? C18 C17 C16 119.07(13) . . ? N4 C18 C17 122.46(13) . . ? C20 C19 C24 120.57(13) . . ? C21 C20 C19 120.39(14) . . ? C22 C21 C20 119.33(12) . . ? C21 C22 C23 120.83(14) . . ? C22 C23 C24 120.16(13) . . ? C23 C24 C19 118.70(10) . . ? C23 C24 C25 122.73(10) . . ? C19 C24 C25 118.54(10) . . ? O1 C25 C26 125.93(10) . . ? O1 C25 C24 114.79(10) . . ? C26 C25 C24 119.26(10) . . ? C27 C26 C25 127.46(10) . . ? O2 C27 C26 126.32(10) . . ? O2 C27 C28 114.97(9) . . ? C26 C27 C28 118.70(10) . . ? C33 C28 C29 118.67(11) . . ? C33 C28 C27 118.84(10) . . ? C29 C28 C27 122.43(10) . . ? C30 C29 C28 120.55(11) . . ? C31 C30 C29 120.44(13) . . ? C32 C31 C30 119.46(13) . . ? C31 C32 C33 120.54(12) . . ? C32 C33 C28 120.33(12) . . ? C1 N1 C5 118.63(11) . . ? C1 N1 Ru1 129.34(8) . . ? C5 N1 Ru1 111.92(8) . . ? C13 N2 C6 112.24(10) . . ? C13 N2 C7 111.80(11) . . ? C6 N2 C7 110.66(10) . . ? C13 N2 Ru1 105.40(7) . . ? C6 N2 Ru1 105.60(7) . . ? C7 N2 Ru1 110.85(7) . . ? C12 N3 C8 118.50(11) . . ? C12 N3 Ru1 125.90(9) . . ? C8 N3 Ru1 115.59(8) . . ? C18 N4 C14 118.62(11) . . ? C18 N4 Ru1 129.14(9) . . ? C14 N4 Ru1 112.17(8) . . ? C25 O1 Ru1 123.92(7) . . ? C27 O2 Ru1 123.00(7) . . ? O11 Cl1 O13 111.46(9) . . ? O11 Cl1 O14 110.09(8) . . ? O13 Cl1 O14 108.99(8) . . ? O11 Cl1 O12 108.53(8) . . ? O13 Cl1 O12 108.89(10) . . ? O14 Cl1 O12 108.84(9) . . ? N3 Ru1 N4 92.18(4) . . ? N3 Ru1 N1 92.23(4) . . ? N4 Ru1 N1 165.53(4) . . ? N3 Ru1 O1 93.04(4) . . ? N4 Ru1 O1 94.91(4) . . ? N1 Ru1 O1 98.60(4) . . ? N3 Ru1 N2 83.23(4) . . ? N4 Ru1 N2 83.60(4) . . ? N1 Ru1 N2 83.25(4) . . ? O1 Ru1 N2 175.92(4) . . ? N3 Ru1 O2 174.25(4) . . ? N4 Ru1 O2 89.25(4) . . ? N1 Ru1 O2 85.07(4) . . ? O1 Ru1 O2 92.39(3) . . ? N2 Ru1 O2 91.39(4) . . ? Cl41 C40 Cl40 120.0(3) . . ? Cl50 C50 Cl51 112.7(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 36.27 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.989 _refine_diff_density_min -0.598 _refine_diff_density_rms 0.074 _database_code_depnum_ccdc_archive 'CCDC 941517' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_twh11jp14 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H58 Cl4 Co2 N8 O21' _chemical_formula_weight 1558.86 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' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.1898(3) _cell_length_b 11.3905(4) _cell_length_c 16.2931(6) _cell_angle_alpha 78.018(3) _cell_angle_beta 82.142(3) _cell_angle_gamma 76.846(3) _cell_volume 1617.39(10) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12676 _cell_measurement_theta_min 3.1622 _cell_measurement_theta_max 31.0663 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.174 _exptl_crystal_size_mid 0.101 _exptl_crystal_size_min 0.026 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.765 _exptl_absorpt_correction_T_min 0.91162 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_crystal_treatment ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Agilent SuperNova Dual diffractometer with an Atlas detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.5861 _diffrn_reflns_number 27884 _diffrn_reflns_av_R_equivalents 0.0357 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6332 _reflns_number_gt 5460 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ; WinGX (Farrugia, 1999) SHELXTL (Bruker, 2003) ORTEP-3 (Farrugia, 1997) ; _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.055P)^2^+3.7P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6332 _refine_ls_number_parameters 460 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0489 _refine_ls_wR_factor_ref 0.1268 _refine_ls_wR_factor_gt 0.1210 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Co1 Co 0.30535(4) 0.24260(3) 0.26379(2) 0.01625(12) Uani 1 1 d . . . N1 N 0.3632(3) 0.3980(2) 0.24673(14) 0.0179(5) Uani 1 1 d . . . N2 N 0.4706(3) 0.1836(2) 0.33444(15) 0.0188(5) Uani 1 1 d . . . N3 N 0.1818(3) 0.2845(2) 0.36269(15) 0.0185(5) Uani 1 1 d . . . N4 N 0.2772(3) 0.0760(2) 0.29304(15) 0.0222(5) Uani 1 1 d . . . C1 C 0.2766(3) 0.5085(3) 0.22219(18) 0.0216(6) Uani 1 1 d . . . H1 H 0.1785 0.5134 0.2076 0.026 Uiso 1 1 calc R . . C2 C 0.3267(4) 0.6147(3) 0.2178(2) 0.0269(7) Uani 1 1 d . . . H2 H 0.2639 0.6923 0.2004 0.032 Uiso 1 1 calc R . . C3 C 0.4692(4) 0.6071(3) 0.2388(2) 0.0312(7) Uani 1 1 d . . . H3 H 0.5065 0.6796 0.2347 0.037 Uiso 1 1 calc R . . C4 C 0.5577(4) 0.4935(3) 0.2661(2) 0.0284(7) Uani 1 1 d . . . H4 H 0.6554 0.4868 0.2819 0.034 Uiso 1 1 calc R . . C5 C 0.5009(3) 0.3899(3) 0.26976(19) 0.0220(6) Uani 1 1 d . . . C6 C 0.5840(3) 0.2613(3) 0.2978(2) 0.0237(6) Uani 1 1 d . . . H6A H 0.6515 0.2594 0.3406 0.028 Uiso 1 1 calc R . . H6B H 0.6456 0.2294 0.2492 0.028 Uiso 1 1 calc R . . C7 C 0.4149(4) 0.1976(3) 0.42395(19) 0.0313(8) Uani 1 1 d . . . H7A H 0.4280 0.1155 0.4605 0.038 Uiso 1 1 calc R . . H7B H 0.4759 0.2457 0.4436 0.038 Uiso 1 1 calc R . . C8 C 0.2539(3) 0.2598(3) 0.43222(18) 0.0214(6) Uani 1 1 d . . . C9 C 0.1819(4) 0.2893(3) 0.50804(19) 0.0269(7) Uani 1 1 d . . . H9 H 0.2350 0.2709 0.5568 0.032 Uiso 1 1 calc R . . C10 C 0.0327(4) 0.3456(3) 0.5116(2) 0.0293(7) Uani 1 1 d . . . H10 H -0.0193 0.3660 0.5630 0.035 Uiso 1 1 calc R . . C11 C -0.0408(4) 0.3723(3) 0.4392(2) 0.0313(7) Uani 1 1 d . . . H11 H -0.1437 0.4119 0.4401 0.038 Uiso 1 1 calc R . . C12 C 0.0363(3) 0.3409(3) 0.3661(2) 0.0246(6) Uani 1 1 d . . . H12 H -0.0144 0.3596 0.3165 0.029 Uiso 1 1 calc R . . C13 C 0.5283(4) 0.0513(3) 0.3288(2) 0.0247(6) Uani 1 1 d . . . H13A H 0.5820 0.0080 0.3787 0.030 Uiso 1 1 calc R . . H13B H 0.5990 0.0438 0.2777 0.030 Uiso 1 1 calc R . . C14 C 0.3967(4) -0.0041(3) 0.32509(19) 0.0247(6) Uani 1 1 d . . . C15 C 0.3951(4) -0.1280(3) 0.3509(2) 0.0321(7) Uani 1 1 d . . . H15 H 0.4807 -0.1840 0.3723 0.039 Uiso 1 1 calc R . . C16 C 0.2672(4) -0.1678(3) 0.3447(2) 0.0361(8) Uani 1 1 d . . . H16 H 0.2630 -0.2519 0.3631 0.043 Uiso 1 1 calc R . . C17 C 0.1455(4) -0.0859(3) 0.3120(2) 0.0351(8) Uani 1 1 d . . . H17 H 0.0572 -0.1128 0.3068 0.042 Uiso 1 1 calc R . . C18 C 0.1532(4) 0.0362(3) 0.2868(2) 0.0282(7) Uani 1 1 d . . . H18 H 0.0689 0.0933 0.2646 0.034 Uiso 1 1 calc R . . O1 O 0.1408(2) 0.30201(18) 0.19902(12) 0.0200(4) Uani 1 1 d . . . O2 O 0.4439(2) 0.19715(18) 0.17352(12) 0.0200(4) Uani 1 1 d . . . C19 C -0.1044(3) 0.4381(3) 0.11251(19) 0.0254(7) Uani 1 1 d . . . H19 H -0.0827 0.4716 0.1572 0.030 Uiso 1 1 calc R . . C20 C -0.2382(4) 0.4855(3) 0.0762(2) 0.0308(7) Uani 1 1 d . . . H20 H -0.3067 0.5530 0.0948 0.037 Uiso 1 1 calc R . . C21 C -0.2725(3) 0.4349(3) 0.0129(2) 0.0300(7) Uani 1 1 d . . . H21 H -0.3652 0.4665 -0.0111 0.036 Uiso 1 1 calc R . . C22 C -0.1720(4) 0.3383(3) -0.0153(2) 0.0287(7) Uani 1 1 d . . . H22 H -0.1961 0.3033 -0.0585 0.034 Uiso 1 1 calc R . . C23 C -0.0371(3) 0.2927(3) 0.01881(19) 0.0235(6) Uani 1 1 d . . . H23 H 0.0325 0.2275 -0.0018 0.028 Uiso 1 1 calc R . . C24 C -0.0016(3) 0.3420(3) 0.08390(18) 0.0183(6) Uani 1 1 d . . . C25 C 0.1433(3) 0.2932(2) 0.12119(18) 0.0174(6) Uani 1 1 d . . . C26 C 0.2686(3) 0.2429(3) 0.07226(18) 0.0215(6) Uani 1 1 d . . . H26 H 0.2559 0.2391 0.0160 0.026 Uiso 1 1 calc R . . C27 C 0.4112(3) 0.1976(2) 0.09935(17) 0.0172(6) Uani 1 1 d . . . C28 C 0.5384(3) 0.1438(2) 0.04239(18) 0.0176(6) Uani 1 1 d . . . C29 C 0.5274(3) 0.1536(3) -0.04372(18) 0.0209(6) Uani 1 1 d . . . H29 H 0.4374 0.1971 -0.0676 0.025 Uiso 1 1 calc R . . C30 C 0.6474(3) 0.1002(3) -0.09425(19) 0.0231(6) Uani 1 1 d . . . H30 H 0.6390 0.1071 -0.1526 0.028 Uiso 1 1 calc R . . C31 C 0.7795(3) 0.0368(3) -0.0604(2) 0.0245(6) Uani 1 1 d . . . H31 H 0.8620 0.0017 -0.0956 0.029 Uiso 1 1 calc R . . C32 C 0.7907(3) 0.0248(3) 0.0252(2) 0.0261(7) Uani 1 1 d . . . H32 H 0.8802 -0.0203 0.0489 0.031 Uiso 1 1 calc R . . C33 C 0.6718(3) 0.0783(3) 0.07589(19) 0.0237(6) Uani 1 1 d . . . H33 H 0.6808 0.0704 0.1343 0.028 Uiso 1 1 calc R . . Cl1 Cl 0.85023(9) 0.74543(7) 0.22592(5) 0.02850(19) Uani 1 1 d . . . O11 O 0.7657(5) 0.8232(3) 0.2797(2) 0.0921(14) Uani 1 1 d . . . O12 O 0.9747(3) 0.7964(3) 0.1838(2) 0.0594(8) Uani 1 1 d . . . O13 O 0.9033(4) 0.6273(3) 0.2745(2) 0.0653(9) Uani 1 1 d . . . O14 O 0.7642(4) 0.7329(3) 0.1633(2) 0.0612(9) Uani 1 1 d . . . Cl2 Cl 0.5306(3) 0.4768(2) 0.51494(14) 0.0453(6) Uani 0.50 1 d P A -1 O21 O 0.5004(9) 0.5693(6) 0.4664(5) 0.0504(8) Uiso 0.50 1 d P A -1 O22 O 0.6408(7) 0.4838(5) 0.5630(4) 0.0504(8) Uiso 0.50 1 d P A -1 O23 O 0.5898(7) 0.3751(5) 0.4702(4) 0.0504(8) Uiso 0.50 1 d P A -1 O24 O 0.4095(7) 0.4258(5) 0.5721(4) 0.0504(8) Uiso 0.50 1 d P A -1 Cl3 Cl 0.8482(2) 0.07181(19) 0.44785(11) 0.0384(4) Uani 0.50 1 d P B -2 O31 O 0.8474(6) 0.0636(5) 0.3630(4) 0.0481(13) Uiso 0.50 1 d P B -2 O32 O 0.7830(10) -0.0151(8) 0.4978(6) 0.086(2) Uiso 0.50 1 d P B -2 O33 O 0.7603(6) 0.1908(5) 0.4618(4) 0.0475(13) Uiso 0.50 1 d P B -2 O34 O 1.0006(8) 0.0709(6) 0.4657(4) 0.0650(17) Uiso 0.50 1 d P B -2 O3 O 0.7598(10) 0.0840(8) 0.4591(5) 0.072(2) Uiso 0.50 1 d P C -3 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 Co1 0.0184(2) 0.0163(2) 0.0144(2) -0.00430(15) -0.00256(14) -0.00258(14) N1 0.0197(12) 0.0190(12) 0.0151(12) -0.0047(9) -0.0003(9) -0.0035(9) N2 0.0214(12) 0.0198(12) 0.0151(12) -0.0044(10) -0.0035(9) -0.0021(10) N3 0.0218(12) 0.0170(12) 0.0179(12) -0.0045(10) -0.0010(10) -0.0056(9) N4 0.0285(13) 0.0209(13) 0.0188(12) -0.0054(10) -0.0023(10) -0.0068(10) C1 0.0269(15) 0.0190(14) 0.0186(14) -0.0044(12) -0.0013(12) -0.0040(12) C2 0.0346(17) 0.0192(15) 0.0256(16) -0.0055(13) -0.0001(13) -0.0035(13) C3 0.0349(18) 0.0231(16) 0.0392(19) -0.0103(14) 0.0027(15) -0.0130(14) C4 0.0235(15) 0.0287(17) 0.0359(18) -0.0101(14) 0.0009(13) -0.0093(13) C5 0.0220(14) 0.0254(16) 0.0195(14) -0.0081(12) 0.0028(11) -0.0057(12) C6 0.0176(14) 0.0249(16) 0.0295(16) -0.0072(13) -0.0034(12) -0.0034(12) C7 0.0300(17) 0.048(2) 0.0145(15) -0.0080(14) -0.0048(13) -0.0019(15) C8 0.0274(15) 0.0187(14) 0.0188(14) -0.0026(12) -0.0019(12) -0.0075(12) C9 0.0364(17) 0.0278(16) 0.0182(15) -0.0049(13) -0.0010(13) -0.0103(14) C10 0.0353(17) 0.0284(17) 0.0260(17) -0.0123(14) 0.0079(14) -0.0101(14) C11 0.0258(16) 0.0346(18) 0.0341(19) -0.0141(15) 0.0021(14) -0.0036(14) C12 0.0240(15) 0.0243(16) 0.0257(16) -0.0079(13) -0.0030(12) -0.0021(12) C13 0.0305(16) 0.0183(15) 0.0230(15) -0.0018(12) -0.0064(13) 0.0000(12) C14 0.0356(17) 0.0215(15) 0.0170(14) -0.0036(12) -0.0030(12) -0.0051(13) C15 0.049(2) 0.0215(16) 0.0248(17) -0.0039(13) -0.0031(15) -0.0059(14) C16 0.060(2) 0.0234(17) 0.0275(18) -0.0068(14) 0.0034(16) -0.0164(16) C17 0.048(2) 0.0325(19) 0.0323(19) -0.0104(15) -0.0013(16) -0.0206(16) C18 0.0328(17) 0.0288(17) 0.0269(17) -0.0087(13) -0.0026(13) -0.0111(14) O1 0.0206(10) 0.0240(11) 0.0158(10) -0.0072(8) -0.0032(8) -0.0014(8) O2 0.0204(10) 0.0215(10) 0.0179(10) -0.0064(8) -0.0037(8) -0.0003(8) C19 0.0288(16) 0.0250(16) 0.0209(15) -0.0064(13) -0.0031(12) -0.0001(13) C20 0.0243(16) 0.0324(18) 0.0285(17) -0.0046(14) -0.0015(13) 0.0073(13) C21 0.0202(15) 0.0353(18) 0.0304(17) -0.0001(14) -0.0071(13) 0.0003(13) C22 0.0295(16) 0.0298(17) 0.0299(17) -0.0074(14) -0.0103(14) -0.0064(13) C23 0.0237(15) 0.0217(15) 0.0247(16) -0.0069(12) -0.0069(12) 0.0012(12) C24 0.0195(14) 0.0166(14) 0.0176(14) -0.0016(11) -0.0029(11) -0.0021(11) C25 0.0223(14) 0.0135(13) 0.0178(14) -0.0036(11) -0.0027(11) -0.0052(11) C26 0.0235(15) 0.0243(15) 0.0171(14) -0.0073(12) -0.0058(11) -0.0002(12) C27 0.0226(14) 0.0116(13) 0.0173(14) -0.0013(11) -0.0026(11) -0.0043(11) C28 0.0202(14) 0.0143(13) 0.0194(14) -0.0035(11) -0.0016(11) -0.0053(11) C29 0.0216(14) 0.0200(14) 0.0203(15) -0.0048(12) -0.0028(11) -0.0010(11) C30 0.0295(16) 0.0216(15) 0.0185(15) -0.0062(12) 0.0019(12) -0.0060(12) C31 0.0238(15) 0.0214(15) 0.0273(16) -0.0090(13) 0.0056(12) -0.0032(12) C32 0.0195(14) 0.0286(16) 0.0294(17) -0.0076(13) -0.0038(12) -0.0004(12) C33 0.0243(15) 0.0255(16) 0.0213(15) -0.0059(12) -0.0049(12) -0.0021(12) Cl1 0.0288(4) 0.0278(4) 0.0262(4) -0.0069(3) -0.0040(3) 0.0024(3) O11 0.128(3) 0.060(2) 0.056(2) -0.0199(18) 0.028(2) 0.033(2) O12 0.0468(17) 0.080(2) 0.061(2) -0.0117(17) -0.0091(15) -0.0314(16) O13 0.084(2) 0.0404(17) 0.056(2) 0.0045(15) -0.0163(17) 0.0126(16) O14 0.0568(19) 0.075(2) 0.061(2) 0.0033(17) -0.0306(16) -0.0308(17) Cl2 0.0400(16) 0.064(2) 0.0346(15) -0.0144(13) 0.0072(9) -0.0175(12) Cl3 0.0311(9) 0.0578(12) 0.0263(8) -0.0100(8) 0.0045(7) -0.0111(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Co1 O1 1.8794(19) . ? Co1 O2 1.886(2) . ? Co1 N1 1.918(2) . ? Co1 N3 1.920(2) . ? Co1 N4 1.926(3) . ? Co1 N2 1.943(2) . ? N1 C1 1.341(4) . ? N1 C5 1.346(4) . ? N2 C13 1.497(4) . ? N2 C6 1.501(4) . ? N2 C7 1.507(4) . ? N3 C8 1.338(4) . ? N3 C12 1.345(4) . ? N4 C18 1.341(4) . ? N4 C14 1.347(4) . ? C1 C2 1.374(4) . ? C2 C3 1.378(5) . ? C3 C4 1.384(5) . ? C4 C5 1.382(4) . ? C5 C6 1.499(4) . ? C7 C8 1.489(4) . ? C8 C9 1.387(4) . ? C9 C10 1.374(5) . ? C10 C11 1.384(5) . ? C11 C12 1.371(4) . ? C13 C14 1.499(4) . ? C14 C15 1.388(4) . ? C15 C16 1.376(5) . ? C16 C17 1.374(5) . ? C17 C18 1.381(5) . ? O1 C25 1.289(3) . ? O2 C27 1.284(3) . ? C19 C20 1.385(4) . ? C19 C24 1.389(4) . ? C20 C21 1.383(5) . ? C21 C22 1.380(5) . ? C22 C23 1.375(4) . ? C23 C24 1.404(4) . ? C24 C25 1.482(4) . ? C25 C26 1.389(4) . ? C26 C27 1.390(4) . ? C27 C28 1.489(4) . ? C28 C33 1.399(4) . ? C28 C29 1.400(4) . ? C29 C30 1.385(4) . ? C30 C31 1.384(4) . ? C31 C32 1.389(4) . ? C32 C33 1.380(4) . ? Cl1 O11 1.407(3) . ? Cl1 O14 1.421(3) . ? Cl1 O13 1.428(3) . ? Cl1 O12 1.428(3) . ? Cl2 O21 1.180(8) . ? Cl2 O22 1.386(6) . ? Cl2 O23 1.458(6) . ? Cl2 O24 1.493(7) . ? Cl3 O32 1.343(9) . ? Cl3 O31 1.406(6) . ? Cl3 O33 1.456(6) . ? Cl3 O34 1.467(7) . ? 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 Co1 O2 95.22(8) . . ? O1 Co1 N1 94.56(9) . . ? O2 Co1 N1 90.73(9) . . ? O1 Co1 N3 90.76(9) . . ? O2 Co1 N3 173.98(9) . . ? N1 Co1 N3 88.14(10) . . ? O1 Co1 N4 95.73(10) . . ? O2 Co1 N4 88.49(10) . . ? N1 Co1 N4 169.71(10) . . ? N3 Co1 N4 91.56(10) . . ? O1 Co1 N2 177.76(9) . . ? O2 Co1 N2 87.00(9) . . ? N1 Co1 N2 85.12(10) . . ? N3 Co1 N2 87.01(10) . . ? N4 Co1 N2 84.60(10) . . ? C1 N1 C5 119.9(3) . . ? C1 N1 Co1 126.4(2) . . ? C5 N1 Co1 113.39(19) . . ? C13 N2 C6 112.6(2) . . ? C13 N2 C7 110.7(2) . . ? C6 N2 C7 111.6(2) . . ? C13 N2 Co1 106.51(17) . . ? C6 N2 Co1 105.54(17) . . ? C7 N2 Co1 109.64(18) . . ? C8 N3 C12 119.1(3) . . ? C8 N3 Co1 114.7(2) . . ? C12 N3 Co1 126.1(2) . . ? C18 N4 C14 119.7(3) . . ? C18 N4 Co1 126.8(2) . . ? C14 N4 Co1 113.5(2) . . ? N1 C1 C2 121.4(3) . . ? C1 C2 C3 119.1(3) . . ? C2 C3 C4 119.7(3) . . ? C5 C4 C3 118.6(3) . . ? N1 C5 C4 121.3(3) . . ? N1 C5 C6 114.3(3) . . ? C4 C5 C6 124.4(3) . . ? C5 C6 N2 108.1(2) . . ? C8 C7 N2 112.2(2) . . ? N3 C8 C9 121.7(3) . . ? N3 C8 C7 116.3(3) . . ? C9 C8 C7 121.9(3) . . ? C10 C9 C8 119.0(3) . . ? C9 C10 C11 119.0(3) . . ? C12 C11 C10 119.4(3) . . ? N3 C12 C11 121.8(3) . . ? N2 C13 C14 108.1(2) . . ? N4 C14 C15 121.3(3) . . ? N4 C14 C13 114.7(3) . . ? C15 C14 C13 124.1(3) . . ? C16 C15 C14 118.7(3) . . ? C17 C16 C15 119.9(3) . . ? C16 C17 C18 119.1(3) . . ? N4 C18 C17 121.3(3) . . ? C25 O1 Co1 124.61(18) . . ? C27 O2 Co1 125.53(18) . . ? C20 C19 C24 120.2(3) . . ? C21 C20 C19 120.2(3) . . ? C22 C21 C20 120.0(3) . . ? C23 C22 C21 120.3(3) . . ? C22 C23 C24 120.4(3) . . ? C19 C24 C23 118.9(3) . . ? C19 C24 C25 120.4(3) . . ? C23 C24 C25 120.8(2) . . ? O1 C25 C26 125.2(3) . . ? O1 C25 C24 115.2(2) . . ? C26 C25 C24 119.7(3) . . ? C25 C26 C27 124.9(3) . . ? O2 C27 C26 124.0(3) . . ? O2 C27 C28 115.0(2) . . ? C26 C27 C28 121.0(3) . . ? C33 C28 C29 118.6(3) . . ? C33 C28 C27 119.4(3) . . ? C29 C28 C27 122.0(3) . . ? C30 C29 C28 120.2(3) . . ? C31 C30 C29 120.6(3) . . ? C30 C31 C32 119.7(3) . . ? C33 C32 C31 120.1(3) . . ? C32 C33 C28 120.8(3) . . ? O11 Cl1 O14 111.8(3) . . ? O11 Cl1 O13 109.3(2) . . ? O14 Cl1 O13 109.2(2) . . ? O11 Cl1 O12 109.1(2) . . ? O14 Cl1 O12 107.69(19) . . ? O13 Cl1 O12 109.7(2) . . ? O21 Cl2 O22 110.0(5) . . ? O21 Cl2 O23 110.1(4) . . ? O22 Cl2 O23 107.6(4) . . ? O21 Cl2 O24 120.1(4) . . ? O22 Cl2 O24 108.8(4) . . ? O23 Cl2 O24 99.1(4) . . ? O32 Cl3 O31 109.6(5) . . ? O32 Cl3 O33 107.9(5) . . ? O31 Cl3 O33 108.8(3) . . ? O32 Cl3 O34 115.1(5) . . ? O31 Cl3 O34 110.2(4) . . ? O33 Cl3 O34 105.0(4) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.194 _refine_diff_density_min -1.594 _refine_diff_density_rms 0.083 _database_code_depnum_ccdc_archive 'CCDC 941518'