# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Jonathan Steed' _publ_contact_author_address ; Department of Chemistry University of Durham University Science Laboratories South Road Durham DH1 3LE UNITED KINGDOM ; _publ_contact_author_email JON.STEED@DUR.AC.UK _publ_section_title ; Simultaneous anion and cation binding by a simple polymer-bound ureidopyridyl ligand ; loop_ _publ_author_name 'Jonathan Steed' 'J. Howard' 'Andrew D.M. Parker' 'Ivana Radosavljevic-Evans' ; J.M.Russell ; data_C:CUTUPC2C.CIF _database_code_depnum_ccdc_archive 'CCDC 285684' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'CuTUP nitrate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H56 Cu N14 O12' _chemical_formula_weight 1132.65 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' O O 0.0106 0.0060 '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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 25.131(3) _cell_length_b 12.5908(13) _cell_length_c 16.6161(18) _cell_angle_alpha 90.00 _cell_angle_beta 91.327(2) _cell_angle_gamma 90.00 _cell_volume 5256.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description irregular _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2364 _exptl_absorpt_coefficient_mu 0.493 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.8582 _exptl_absorpt_correction_T_max 0.9524 _exptl_absorpt_process_details ? _exptl_special_details ; The structure could also be solved without disorder in P21/n. However, refinement of this lower symmetry structure led to rather higher R values. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source microsource _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 34263 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0349 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 30.00 _reflns_number_total 7657 _reflns_number_gt 5941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V5.625 (Bruker, 2001)' _computing_cell_refinement 'SMART V5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSeed interface to POVRay' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _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^)+(0.0593P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7657 _refine_ls_number_parameters 467 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0916 _refine_ls_goodness_of_fit_ref 0.968 _refine_ls_restrained_S_all 0.969 _refine_ls_shift/su_max 0.018 _refine_ls_shift/su_mean 0.001 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 Cu1 Cu 0.2500 0.2500 0.5000 0.02089(7) Uani 1 2 d S . . O1 O 0.35337(3) -0.12518(7) 0.21889(5) 0.02486(19) Uani 1 1 d . . . N1 N 0.27432(4) 0.17552(8) 0.39777(7) 0.0217(2) Uani 1 1 d . . . N4 N 0.17811(4) 0.17364(8) 0.49841(6) 0.0197(2) Uani 1 1 d . . . O6 O 0.18559(4) -0.36501(8) 0.47980(7) 0.0344(2) Uani 1 1 d . . . N3 N 0.32503(4) -0.26276(8) 0.29643(7) 0.0212(2) Uani 1 1 d . . . O3 O 0.28908(5) 0.09969(9) 0.58236(8) 0.0452(3) Uani 1 1 d . . . O2 O 0.03874(3) -0.11490(7) 0.56840(6) 0.0300(2) Uani 1 1 d . B . N9 N 0.21817(4) -0.31759(8) 0.43712(6) 0.0216(2) Uani 1 1 d . . . O4 O 0.21423(4) -0.22044(8) 0.42480(7) 0.0338(2) Uani 1 1 d . . . N6 N 0.09252(4) -0.25974(8) 0.55019(7) 0.0227(2) Uani 1 1 d . B . N5 N 0.12388(4) -0.09256(8) 0.52499(7) 0.0236(2) Uani 1 1 d . B . N2 N 0.30219(4) -0.09285(8) 0.32865(7) 0.0225(2) Uani 1 1 d . . . O5 O 0.25531(4) -0.36974(9) 0.40752(7) 0.0417(3) Uani 1 1 d . . . C6 C 0.32914(4) -0.15892(10) 0.27689(7) 0.0185(2) Uani 1 1 d . B . C5 C 0.27999(4) 0.07020(9) 0.39235(8) 0.0199(2) Uani 1 1 d . B . H5 H 0.2685 0.0278 0.4359 0.024 Uiso 1 1 calc R A 1 C7 C 0.3561(4) -0.3388(8) 0.2598(8) 0.0172(15) Uani 0.546(11) 1 d P B 1 C17 C 0.12361(4) 0.01760(9) 0.51608(7) 0.0195(2) Uani 1 1 d . . . C4 C 0.3031(5) 0.0159(9) 0.3222(7) 0.0199(17) Uani 0.546(11) 1 d P B 1 C20 C 0.05945(5) -0.34277(10) 0.57804(8) 0.0220(2) Uani 1 1 d . . . C18 C 0.17265(4) 0.06911(9) 0.51112(7) 0.0184(2) Uani 1 1 d . B . H18 H 0.2040 0.0275 0.5171 0.022 Uiso 1 1 calc R . . C19 C 0.08127(4) -0.15385(10) 0.54978(8) 0.0212(2) Uani 1 1 d . . . C21 C 0.01377(5) -0.32612(11) 0.62283(9) 0.0313(3) Uani 1 1 d . . . H21 H 0.0034 -0.2561 0.6369 0.038 Uiso 1 1 calc R . . C16 C 0.07770(5) 0.07995(10) 0.50913(10) 0.0319(3) Uani 1 1 d . B . H16 H 0.0434 0.0489 0.5127 0.038 Uiso 1 1 calc R . . C25 C 0.07473(5) -0.44640(11) 0.56165(9) 0.0315(3) Uani 1 1 d . . . H25 H 0.1062 -0.4591 0.5326 0.038 Uiso 1 1 calc R . . C10A C 0.4137(5) -0.5105(9) 0.2034(8) 0.0264(19) Uani 0.454(11) 1 d P B 2 C23 C -0.00218(5) -0.51631(11) 0.62881(9) 0.0322(3) Uani 1 1 d . . . C22 C -0.01638(6) -0.41295(11) 0.64668(10) 0.0348(3) Uani 1 1 d . . . H22 H -0.0477 -0.4008 0.6762 0.042 Uiso 1 1 calc R . . C14 C 0.13344(5) 0.23269(10) 0.49150(10) 0.0325(3) Uani 1 1 d . B . H14 H 0.1364 0.3070 0.4827 0.039 Uiso 1 1 calc R . . C24 C 0.04438(6) -0.53153(11) 0.58735(10) 0.0385(4) Uani 1 1 d . . . H24 H 0.0558 -0.6018 0.5762 0.046 Uiso 1 1 calc R . . C9 C 0.43144(6) -0.42185(13) 0.20135(11) 0.0435(4) Uani 1 1 d . . . H9 H 0.4670 -0.4131 0.1845 0.052 Uiso 1 1 calc R B 1 C15 C 0.08355(5) 0.18789(11) 0.49689(11) 0.0405(4) Uani 1 1 d . . . H15 H 0.0529 0.2317 0.4921 0.049 Uiso 1 1 calc R B . C8 C 0.40439(6) -0.33460(13) 0.23212(12) 0.0481(5) Uani 1 1 d . B . H8 H 0.4221 -0.2680 0.2330 0.058 Uiso 1 1 calc R C 1 C13 C 0.4356(7) -0.6162(10) 0.1669(7) 0.045(2) Uani 0.546(11) 1 d P B 1 H13A H 0.4675 -0.5908 0.1400 0.068 Uiso 0.546(11) 1 calc PR B 1 H13B H 0.4137 -0.6578 0.1289 0.068 Uiso 0.546(11) 1 calc PR B 1 H13C H 0.4462 -0.6609 0.2129 0.068 Uiso 0.546(11) 1 calc PR B 1 C26 C -0.03643(7) -0.60938(12) 0.65330(12) 0.0457(4) Uani 1 1 d . . . H26A H -0.0476 -0.5996 0.7089 0.069 Uiso 1 1 calc R . . H26B H -0.0159 -0.6753 0.6493 0.069 Uiso 1 1 calc R . . H26C H -0.0679 -0.6135 0.6175 0.069 Uiso 1 1 calc R . . C1 C 0.2991(2) 0.2335(4) 0.3334(3) 0.0205(8) Uani 0.546(11) 1 d P B 1 H1 H 0.2975 0.3089 0.3342 0.025 Uiso 0.546(11) 1 calc PR B 1 H3N H 0.3057(6) -0.2790(12) 0.3299(9) 0.019(4) Uiso 1 1 d . . . H2N H 0.2866(6) -0.1194(13) 0.3688(10) 0.036(4) Uiso 1 1 d . . . H6N H 0.1196(6) -0.2777(11) 0.5296(9) 0.020(4) Uiso 1 1 d . . . H5N H 0.1549(6) -0.1220(13) 0.5177(10) 0.038(4) Uiso 1 1 d . . . H32O H 0.3082(7) 0.1103(14) 0.6194(12) 0.042(5) Uiso 1 1 d . . . H31O H 0.2895(11) 0.040(2) 0.5785(17) 0.110(11) Uiso 1 1 d . . . C11 C 0.35235(19) -0.5317(3) 0.2131(3) 0.0269(8) Uani 0.546(11) 1 d P B 1 H11 H 0.3331 -0.5951 0.2021 0.032 Uiso 0.546(11) 1 calc PR B 1 C2 C 0.3252(3) 0.1850(3) 0.27069(19) 0.0259(9) Uani 0.546(11) 1 d P B 1 H2 H 0.3410 0.2274 0.2305 0.031 Uiso 0.546(11) 1 calc PR B 1 C2A C 0.2998(3) 0.1944(3) 0.2687(2) 0.0211(9) Uani 0.454(11) 1 d P B 2 H2A H 0.3072 0.2399 0.2247 0.025 Uiso 0.454(11) 1 calc PR B 2 C12 C 0.3259(2) -0.4477(4) 0.2470(3) 0.0217(8) Uani 0.546(11) 1 d P B 1 H12 H 0.2899 -0.4551 0.2625 0.026 Uiso 0.546(11) 1 calc PR B 1 C11A C 0.3667(3) -0.5301(4) 0.2443(5) 0.0382(15) Uani 0.454(11) 1 d P B 2 H11A H 0.3547 -0.6006 0.2532 0.046 Uiso 0.454(11) 1 calc PR B 2 C12A C 0.3377(3) -0.4424(5) 0.2718(5) 0.0331(14) Uani 0.454(11) 1 d P B 2 H12A H 0.3060 -0.4545 0.3005 0.040 Uiso 0.454(11) 1 calc PR B 2 C3 C 0.3285(2) 0.0755(4) 0.2659(3) 0.0227(8) Uani 0.546(11) 1 d P B 1 H3 H 0.3480 0.0425 0.2245 0.027 Uiso 0.546(11) 1 calc PR B 1 C3A C 0.3083(3) 0.0862(4) 0.2618(3) 0.0245(10) Uani 0.454(11) 1 d P B 2 H3A H 0.3197 0.0557 0.2128 0.029 Uiso 0.454(11) 1 calc PR B 2 C1A C 0.2807(2) 0.2365(5) 0.3393(4) 0.0184(9) Uani 0.454(11) 1 d P B 2 H1A H 0.2725 0.3099 0.3432 0.022 Uiso 0.454(11) 1 calc PR B 2 C4A C 0.2993(6) 0.0212(9) 0.3321(9) 0.0169(19) Uani 0.454(11) 1 d PU B 2 C10 C 0.4059(4) -0.5283(7) 0.1943(6) 0.0249(14) Uani 0.546(11) 1 d P B 1 C7A C 0.3510(4) -0.3568(9) 0.2608(9) 0.0118(15) Uani 0.454(11) 1 d PU B 2 C13A C 0.4451(9) -0.6129(11) 0.1658(10) 0.055(3) Uani 0.454(11) 1 d P B 2 H13D H 0.4598 -0.5934 0.1137 0.083 Uiso 0.454(11) 1 calc PR B 2 H13E H 0.4201 -0.6721 0.1584 0.083 Uiso 0.454(11) 1 calc PR B 2 H13F H 0.4741 -0.6343 0.2028 0.083 Uiso 0.454(11) 1 calc PR B 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 Cu1 0.01803(11) 0.01288(10) 0.03161(13) -0.00759(8) -0.00291(8) -0.00069(7) O1 0.0258(4) 0.0313(5) 0.0177(4) -0.0005(4) 0.0060(3) -0.0022(4) N1 0.0229(5) 0.0141(5) 0.0278(6) -0.0013(4) -0.0059(4) -0.0006(4) N4 0.0202(5) 0.0150(5) 0.0237(5) -0.0034(4) -0.0023(4) 0.0007(4) O6 0.0273(5) 0.0308(5) 0.0459(6) 0.0050(5) 0.0163(4) -0.0057(4) N3 0.0219(5) 0.0202(5) 0.0217(5) -0.0021(4) 0.0068(4) 0.0015(4) O3 0.0611(8) 0.0186(5) 0.0541(8) 0.0091(5) -0.0384(6) -0.0108(5) O2 0.0177(4) 0.0267(5) 0.0460(6) 0.0096(4) 0.0098(4) 0.0041(3) N9 0.0197(5) 0.0194(5) 0.0259(6) 0.0031(4) 0.0037(4) 0.0023(4) O4 0.0358(5) 0.0178(4) 0.0473(6) 0.0096(4) -0.0097(5) -0.0005(4) N6 0.0157(5) 0.0199(5) 0.0328(6) 0.0038(4) 0.0056(4) 0.0002(4) N5 0.0145(5) 0.0166(5) 0.0399(7) 0.0034(4) 0.0058(4) 0.0024(4) N2 0.0323(6) 0.0153(5) 0.0206(5) 0.0019(4) 0.0116(4) 0.0002(4) O5 0.0402(6) 0.0511(7) 0.0347(6) 0.0158(5) 0.0210(5) 0.0271(5) C6 0.0174(5) 0.0216(6) 0.0165(6) -0.0028(4) 0.0005(4) 0.0007(4) C5 0.0188(5) 0.0153(5) 0.0257(6) 0.0010(5) 0.0040(4) -0.0001(4) C7 0.027(3) 0.004(3) 0.0204(19) -0.0008(17) -0.0022(16) -0.0072(15) C17 0.0182(5) 0.0158(5) 0.0245(6) -0.0007(5) 0.0003(4) 0.0017(4) C4 0.025(3) 0.021(2) 0.013(3) -0.0122(17) 0.0041(18) 0.0010(15) C20 0.0185(5) 0.0206(6) 0.0268(7) 0.0055(5) 0.0012(5) -0.0013(4) C18 0.0173(5) 0.0170(5) 0.0209(6) -0.0010(4) 0.0022(4) 0.0025(4) C19 0.0165(5) 0.0206(6) 0.0266(6) 0.0046(5) 0.0013(4) 0.0001(4) C21 0.0283(7) 0.0229(6) 0.0433(9) 0.0090(6) 0.0141(6) 0.0032(5) C16 0.0175(6) 0.0203(6) 0.0574(10) -0.0037(6) -0.0063(6) 0.0015(5) C25 0.0263(6) 0.0230(7) 0.0459(9) -0.0022(6) 0.0141(6) -0.0041(5) C10A 0.031(3) 0.013(4) 0.035(3) -0.012(2) 0.012(3) 0.006(3) C23 0.0320(7) 0.0262(7) 0.0387(8) 0.0052(6) 0.0092(6) -0.0078(5) C22 0.0277(7) 0.0315(7) 0.0459(9) 0.0109(7) 0.0168(6) 0.0003(6) C14 0.0252(7) 0.0134(6) 0.0583(10) -0.0038(6) -0.0120(6) 0.0025(4) C24 0.0393(8) 0.0211(7) 0.0560(10) -0.0032(7) 0.0183(7) -0.0068(6) C9 0.0299(7) 0.0365(9) 0.0648(12) -0.0165(8) 0.0171(7) 0.0048(6) C15 0.0206(6) 0.0187(6) 0.0814(12) -0.0055(7) -0.0142(7) 0.0050(5) C8 0.0290(7) 0.0312(8) 0.0848(14) -0.0273(8) 0.0201(8) -0.0054(6) C13 0.056(5) 0.034(3) 0.046(4) 0.008(2) 0.029(3) 0.020(3) C26 0.0462(9) 0.0317(8) 0.0601(11) 0.0040(8) 0.0198(8) -0.0150(7) C1 0.028(2) 0.0110(12) 0.0224(15) 0.0028(9) 0.0046(18) -0.0018(16) C11 0.0367(19) 0.0160(13) 0.0277(19) -0.0029(13) -0.0021(13) 0.0013(11) C2 0.037(3) 0.0181(12) 0.0228(13) 0.0028(10) 0.0098(14) -0.0010(14) C2A 0.029(3) 0.0144(14) 0.0196(15) 0.0021(10) 0.0033(15) 0.0023(14) C12 0.0248(18) 0.0135(14) 0.027(2) -0.0030(13) -0.0013(13) -0.0036(12) C11A 0.044(3) 0.0128(15) 0.059(4) -0.006(2) 0.018(3) -0.0029(17) C12A 0.028(3) 0.024(2) 0.048(4) -0.014(3) 0.020(2) -0.0057(19) C3 0.032(2) 0.0155(14) 0.0212(14) 0.0002(10) 0.0073(16) -0.0019(15) C3A 0.036(3) 0.0231(18) 0.0140(15) -0.0023(12) 0.005(2) 0.005(2) C1A 0.019(2) 0.0170(15) 0.0192(17) -0.0028(11) 0.0041(18) -0.0008(18) C4A 0.026(3) 0.010(3) 0.015(3) 0.009(3) 0.004(2) -0.004(2) C10 0.044(3) 0.008(2) 0.023(2) -0.002(2) 0.0043(18) -0.0006(18) C7A 0.012(2) 0.006(4) 0.017(2) -0.002(2) 0.0063(16) 0.002(3) C13A 0.061(7) 0.019(4) 0.086(7) 0.002(3) 0.039(4) 0.022(3) _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 Cu1 N1 2.0461(11) 7_556 ? Cu1 N1 2.0461(11) . ? Cu1 N4 2.0462(10) . ? Cu1 N4 2.0462(10) 7_556 ? Cu1 O3 2.5212(11) . ? O1 C6 1.2277(14) . ? N1 C1A 1.252(6) . ? N1 C5 1.3370(15) . ? N1 C1 1.448(5) . ? N4 C18 1.3406(15) . ? N4 C14 1.3491(16) . ? O6 N9 1.2477(13) . ? N3 C6 1.3517(16) . ? N3 C7 1.384(10) . ? N3 C7A 1.482(10) . ? O2 C19 1.2222(14) . ? N9 O4 1.2439(14) . ? N9 O5 1.2512(13) . ? N6 C19 1.3629(15) . ? N6 C20 1.4197(15) . ? N5 C19 1.3901(15) . ? N5 C17 1.3950(15) . ? N2 C4 1.374(11) . ? N2 C6 1.3847(15) . ? N2 C4A 1.439(11) . ? C5 C4A 1.280(16) . ? C5 C4 1.482(13) . ? C7 C8 1.309(10) . ? C7 C12 1.579(13) . ? C17 C18 1.3968(16) . ? C17 C16 1.3980(16) . ? C4 C3 1.369(12) . ? C20 C25 1.3888(18) . ? C20 C21 1.3983(17) . ? C21 C22 1.3930(18) . ? C16 C15 1.3825(19) . ? C25 C24 1.3885(18) . ? C10A C9 1.202(11) . ? C10A C11A 1.400(13) . ? C10A C13A 1.64(2) . ? C23 C22 1.384(2) . ? C23 C24 1.385(2) . ? C23 C26 1.5152(19) . ? C14 C15 1.3796(19) . ? C9 C8 1.395(2) . ? C9 C10 1.489(9) . ? C8 C7A 1.460(11) . ? C13 C10 1.416(18) . ? C1 C2 1.385(5) . ? C11 C12 1.377(7) . ? C11 C10 1.390(12) . ? C2 C3 1.383(5) . ? C2A C3A 1.384(6) . ? C2A C1A 1.384(6) . ? C11A C12A 1.406(8) . ? C12A C7A 1.145(15) . ? C3A C4A 1.448(13) . ? 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 Cu1 N1 180.00(3) 7_556 . ? N1 Cu1 N4 86.87(4) 7_556 . ? N1 Cu1 N4 93.13(4) . . ? N1 Cu1 N4 93.13(4) 7_556 7_556 ? N1 Cu1 N4 86.87(4) . 7_556 ? N4 Cu1 N4 180.00(3) . 7_556 ? N1 Cu1 O3 90.77(5) 7_556 . ? N1 Cu1 O3 89.23(5) . . ? N4 Cu1 O3 89.26(4) . . ? N4 Cu1 O3 90.74(4) 7_556 . ? C1A N1 C5 122.7(3) . . ? C1A N1 C1 18.6(2) . . ? C5 N1 C1 113.7(2) . . ? C1A N1 Cu1 114.2(3) . . ? C5 N1 Cu1 123.01(9) . . ? C1 N1 Cu1 121.6(2) . . ? C18 N4 C14 117.81(10) . . ? C18 N4 Cu1 123.56(8) . . ? C14 N4 Cu1 118.35(8) . . ? C6 N3 C7 121.1(5) . . ? C6 N3 C7A 129.8(5) . . ? C7 N3 C7A 9.7(8) . . ? O4 N9 O6 120.89(10) . . ? O4 N9 O5 120.58(10) . . ? O6 N9 O5 118.53(11) . . ? C19 N6 C20 126.79(11) . . ? C19 N5 C17 125.56(10) . . ? C4 N2 C6 122.7(6) . . ? C4 N2 C4A 7.9(11) . . ? C6 N2 C4A 130.6(6) . . ? O1 C6 N3 124.42(11) . . ? O1 C6 N2 122.57(11) . . ? N3 C6 N2 113.00(10) . . ? C4A C5 N1 125.0(4) . . ? C4A C5 C4 1.4(10) . . ? N1 C5 C4 123.7(4) . . ? C8 C7 N3 131.6(8) . . ? C8 C7 C12 115.7(7) . . ? N3 C7 C12 112.7(7) . . ? N5 C17 C18 117.76(10) . . ? N5 C17 C16 124.68(11) . . ? C18 C17 C16 117.52(11) . . ? C3 C4 N2 127.5(10) . . ? C3 C4 C5 118.8(8) . . ? N2 C4 C5 113.0(8) . . ? C25 C20 C21 118.64(12) . . ? C25 C20 N6 117.47(11) . . ? C21 C20 N6 123.86(12) . . ? N4 C18 C17 123.97(10) . . ? O2 C19 N6 125.02(11) . . ? O2 C19 N5 122.44(11) . . ? N6 C19 N5 112.54(10) . . ? C22 C21 C20 119.51(13) . . ? C15 C16 C17 118.28(12) . . ? C24 C25 C20 120.57(13) . . ? C9 C10A C11A 119.7(9) . . ? C9 C10A C13A 122.5(11) . . ? C11A C10A C13A 117.7(10) . . ? C22 C23 C24 117.51(12) . . ? C22 C23 C26 121.26(13) . . ? C24 C23 C26 121.23(14) . . ? C23 C22 C21 122.17(13) . . ? N4 C14 C15 121.65(12) . . ? C23 C24 C25 121.51(13) . . ? C10A C9 C8 122.5(6) . . ? C10A C9 C10 7.2(10) . . ? C8 C9 C10 121.7(5) . . ? C14 C15 C16 120.75(12) . . ? C7 C8 C9 124.1(5) . . ? C7 C8 C7A 8.8(8) . . ? C9 C8 C7A 115.3(4) . . ? C2 C1 N1 123.5(4) . . ? C12 C11 C10 123.2(5) . . ? C3 C2 C1 120.9(3) . . ? C3A C2A C1A 120.3(4) . . ? C11 C12 C7 119.2(5) . . ? C10A C11A C12A 118.0(6) . . ? C7A C12A C11A 122.2(7) . . ? C4 C3 C2 118.5(6) . . ? C2A C3A C4A 117.5(7) . . ? N1 C1A C2A 118.4(5) . . ? C5 C4A N2 122.2(9) . . ? C5 C4A C3A 115.3(8) . . ? N2 C4A C3A 121.5(11) . . ? C11 C10 C13 124.6(9) . . ? C11 C10 C9 115.4(7) . . ? C13 C10 C9 120.0(10) . . ? C12A C7A C8 120.4(8) . . ? C12A C7A N3 123.7(9) . . ? C8 C7A N3 113.2(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.366 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.069 # Attachment 'CoTUP.CIF' data_cotup.cif _database_code_depnum_ccdc_archive 'CCDC 285685' _audit_creation_date 05-08-03 _audit_creation_method CRYSTALS_ver_12-03-99 _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 8.9158(6) _cell_angle_alpha 71.6580(10) _cell_length_b 12.7512(9) _cell_angle_beta 75.9930(10) _cell_length_c 13.6583(9) _cell_angle_gamma 73.7080(10) _cell_volume 1394.41(16) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'Co ' 0.3494 0.9721 12.2841 4.2791 7.3409 0.2784 4.0034 13.5359 2.3488 71.1692 1.0118 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 1 _chemical_formula_sum ' C54 H64 Co1 N14 O14 ' _chemical_formula_moiety ' C54 H64 Co1 N14 O14 ' _chemical_compound_source ; ? ; _chemical_formula_weight 1192.12 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description ' irregular ' _exptl_crystal_colour ' pink ' _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 625 _exptl_absorpt_coefficient_mu 0.387 _diffrn_measurement_device_type ; Unknown ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DATA COLLECTION ; _computing_data_reduction ; USER DEFINED 5 ; _computing_cell_refinement ; USER DEFINED 6 ; _computing_structure_solution ; USER DEFINED STRUCTURE SOLUTION ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.98 # Sheldrick geometric definitions 0.94 0.98 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 120 _diffrn_reflns_number 18675 _reflns_number_total 8048 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 8048 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 8124 _diffrn_reflns_theta_min 1.594 _diffrn_reflns_theta_max 29.986 _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.486 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -11 _reflns_limit_h_max 12 _reflns_limit_k_min -16 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _refine_diff_density_min -0.37 _refine_diff_density_max 0.71 _refine_ls_number_reflns 6069 _refine_ls_number_restraints 0 _refine_ls_number_parameters 377 #_refine_ls_R_factor_ref 0.0360 _refine_ls_wR_factor_ref 0.0909 _refine_ls_goodness_of_fit_ref 0.8714 #_reflns_number_all 8024 _refine_ls_R_factor_all 0.0442 _refine_ls_wR_factor_all 0.0944 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 6069 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_gt 0.0909 _refine_ls_shift/su_max 0.000445 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 9.38 14.1 6.24 1.34 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined structure solution reference User-defined data collection reference Spare 5 Spare 6 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group _atom_site_attached_hydrogens Co1 Co 1.0000 0.5000 0.5000 0.0130 1.0000 Uani S . . . . . N1 N 1.21704(14) 0.46226(10) 0.56565(10) 0.0153 1.0000 Uani . . . . . . C1 C 1.23216(17) 0.51854(12) 0.62974(11) 0.0156 1.0000 Uani . . . . . . C5 C 1.37077(17) 0.49943(12) 0.66989(11) 0.0155 1.0000 Uani . . . . . . N2 N 1.36578(15) 0.56504(11) 0.73609(11) 0.0188 1.0000 Uani . . . . . . C6 C 1.48931(17) 0.56096(12) 0.78300(11) 0.0164 1.0000 Uani . . . . . . N3 N 1.44324(16) 0.61594(11) 0.85964(10) 0.0190 1.0000 Uani . . . . . . C7 C 1.54110(19) 0.62768(13) 0.92151(12) 0.0190 1.0000 Uani . . . . . . C12 C 1.4632(2) 0.67595(14) 1.00418(13) 0.0238 1.0000 Uani . . . . . . C11 C 1.5491(2) 0.69682(16) 1.06581(14) 0.0278 1.0000 Uani . . . . . . C10 C 1.7139(2) 0.66863(18) 1.04818(13) 0.0302 1.0000 Uani . . . . . . C9 C 1.7894(2) 0.61758(19) 0.96815(14) 0.0323 1.0000 Uani . . . . . . C8 C 1.7061(2) 0.59667(17) 0.90438(13) 0.0275 1.0000 Uani . . . . . . C13 C 1.8088(3) 0.6936(3) 1.11286(16) 0.0471 1.0000 Uani . . . . . . O1 O 1.62645(13) 0.51097(10) 0.75700(9) 0.0203 1.0000 Uani . . . . . . C4 C 1.49935(18) 0.41487(13) 0.64395(12) 0.0190 1.0000 Uani . . . . . . C3 C 1.48257(18) 0.35624(13) 0.57860(13) 0.0202 1.0000 Uani . . . . . . C2 C 1.34238(17) 0.38151(12) 0.54066(12) 0.0181 1.0000 Uani . . . . . . N4 N 1.05549(14) 0.65789(10) 0.39628(10) 0.0156 1.0000 Uani . . . . . . C18 C 1.09495(17) 0.73147(12) 0.43274(11) 0.0159 1.0000 Uani . . . . . . C17 C 1.12786(17) 0.83510(12) 0.36835(12) 0.0163 1.0000 Uani . . . . . . N5 N 1.16734(16) 0.91308(11) 0.40489(10) 0.0193 1.0000 Uani . . . . . . C19 C 1.22305(17) 0.88971(12) 0.49757(12) 0.0161 1.0000 Uani . . . . . . N6 N 1.25909(16) 0.98196(11) 0.50931(10) 0.0190 1.0000 Uani . . . . . . C20 C 1.32688(18) 0.98205(12) 0.59277(12) 0.0174 1.0000 Uani . . . . . . C25 C 1.42285(19) 0.88611(13) 0.64859(13) 0.0206 1.0000 Uani . . . . . . C24 C 1.4872(2) 0.89373(14) 0.72874(13) 0.0224 1.0000 Uani . . . . . . C23 C 1.4591(2) 0.99510(15) 0.75549(13) 0.0227 1.0000 Uani . . . . . . C22 C 1.3665(2) 1.09077(14) 0.69722(14) 0.0242 1.0000 Uani . . . . . . C21 C 1.30131(19) 1.08498(13) 0.61685(13) 0.0218 1.0000 Uani . . . . . . C26 C 1.5231(2) 0.99998(18) 0.84652(15) 0.0324 1.0000 Uani . . . . . . O2 O 1.23941(14) 0.79634(9) 0.56046(9) 0.0202 1.0000 Uani . . . . . . C16 C 1.11787(19) 0.86199(13) 0.26248(12) 0.0207 1.0000 Uani . . . . . . C15 C 1.0772(2) 0.78581(14) 0.22547(12) 0.0220 1.0000 Uani . . . . . . C14 C 1.04715(18) 0.68469(13) 0.29431(12) 0.0191 1.0000 Uani . . . . . . O3 O 1.12649(13) 0.42013(9) 0.38278(9) 0.0180 1.0000 Uani . . . . . . N7 N 0.92959(16) 0.78334(11) 0.71243(11) 0.0203 1.0000 Uani . . . . . . O5 O 0.90953(18) 0.87008(10) 0.74262(11) 0.0306 1.0000 Uani . . . . . . O6 O 1.01132(14) 0.69153(10) 0.75668(9) 0.0232 1.0000 Uani . . . . . . O4 O 0.86506(15) 0.78866(10) 0.63759(10) 0.0233 1.0000 Uani . . . . . . O7 O 1.12923(17) 0.76178(14) 0.90372(12) 0.0374 1.0000 Uani . . . . . . C27 C 1.1164(3) 0.8758(2) 0.90002(18) 0.0408 1.0000 Uani . . . . . . H11 H 1.13899(17) 0.57743(12) 0.65002(11) 0.0195 1.0000 Uiso R . . . . . H121 H 1.3447(2) 0.69577(14) 1.01908(13) 0.0302 1.0000 Uiso R . . . . . H111 H 1.4914(2) 0.73273(16) 1.12377(14) 0.0356 1.0000 Uiso R . . . . . H91 H 1.9078(2) 0.59467(19) 0.95560(14) 0.0419 1.0000 Uiso R . . . . . H81 H 1.7643(2) 0.55999(17) 0.84699(13) 0.0355 1.0000 Uiso R . . . . . H131 H 1.9245(3) 0.6670(3) 1.08833(16) 0.0657 1.0000 Uiso R . . . . . H132 H 1.7839(3) 0.7770(3) 1.10477(16) 0.0657 1.0000 Uiso R . . . . . H133 H 1.7805(3) 0.6533(3) 1.18819(16) 0.0657 1.0000 Uiso R . . . . . H41 H 1.60020(18) 0.39709(13) 0.67170(12) 0.0235 1.0000 Uiso R . . . . . H31 H 1.57248(18) 0.29516(13) 0.55875(13) 0.0256 1.0000 Uiso R . . . . . H21 H 1.33387(17) 0.33857(12) 0.49304(12) 0.0228 1.0000 Uiso R . . . . . H181 H 1.10084(17) 0.71140(12) 0.50884(11) 0.0200 1.0000 Uiso R . . . . . H251 H 1.44520(19) 0.81216(13) 0.63103(13) 0.0256 1.0000 Uiso R . . . . . H241 H 1.5558(2) 0.82446(14) 0.76811(13) 0.0277 1.0000 Uiso R . . . . . H221 H 1.3466(2) 1.16510(14) 0.71362(14) 0.0315 1.0000 Uiso R . . . . . H211 H 1.23570(19) 1.15494(13) 0.57611(13) 0.0274 1.0000 Uiso R . . . . . H261 H 1.4910(2) 1.07921(18) 0.85383(15) 0.0427 1.0000 Uiso R . . . . . H262 H 1.6414(2) 0.97601(18) 0.83352(15) 0.0427 1.0000 Uiso R . . . . . H263 H 1.4794(2) 0.94791(18) 0.91231(15) 0.0427 1.0000 Uiso R . . . . . H161 H 1.13974(19) 0.93525(13) 0.21394(12) 0.0254 1.0000 Uiso R . . . . . H151 H 1.0696(2) 0.80366(14) 0.14987(12) 0.0275 1.0000 Uiso R . . . . . H141 H 1.01829(18) 0.63013(13) 0.26699(12) 0.0242 1.0000 Uiso R . . . . . H22 H 1.26384(15) 0.61999(11) 0.75077(11) 0.0242 1.0000 Uiso R . . . . . H32 H 1.32795(16) 0.65194(11) 0.87391(10) 0.0245 1.0000 Uiso R . . . . . H51 H 1.15392(16) 0.99295(11) 0.36018(10) 0.0247 1.0000 Uiso R . . . . . H61 H 1.23590(16) 1.05511(11) 0.45453(10) 0.0240 1.0000 Uiso R . . . . . H5 H 1.07004(17) 0.75810(14) 0.87026(12) 0.0500 1.0000 Uiso R . . . . . H271 H 1.1911(3) 0.8794(2) 0.94225(18) 0.0462 1.0000 Uiso R . . . . . H272 H 1.0053(3) 0.9091(2) 0.92931(18) 0.0462 1.0000 Uiso R . . . . . H273 H 1.1436(3) 0.9195(2) 0.82574(18) 0.0462 1.0000 Uiso R . . . . . 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 0.01256(12) 0.01305(12) 0.01604(13) -0.00526(10) -0.00452(9) -0.00379(9) N1 0.0152(5) 0.0149(5) 0.0176(5) -0.0048(4) -0.0047(4) -0.0040(4) C1 0.0145(6) 0.0162(6) 0.0178(6) -0.0053(5) -0.0050(5) -0.0035(5) C5 0.0161(6) 0.0161(6) 0.0165(6) -0.0043(5) -0.0055(5) -0.0046(5) N2 0.0168(6) 0.0210(6) 0.0227(6) -0.0105(5) -0.0086(5) -0.0008(5) C6 0.0174(6) 0.0167(6) 0.0167(6) -0.0021(5) -0.0056(5) -0.0069(5) N3 0.0180(6) 0.0226(6) 0.0207(6) -0.0087(5) -0.0074(5) -0.0041(5) C7 0.0231(7) 0.0200(7) 0.0174(6) -0.0028(5) -0.0081(5) -0.0088(5) C12 0.0287(8) 0.0243(7) 0.0223(7) -0.0073(6) -0.0093(6) -0.0063(6) C11 0.0384(9) 0.0308(8) 0.0210(7) -0.0078(6) -0.0092(7) -0.0138(7) C10 0.0382(10) 0.0432(10) 0.0183(7) -0.0036(7) -0.0085(7) -0.0251(8) C9 0.0271(8) 0.0558(12) 0.0216(8) -0.0091(8) -0.0070(6) -0.0197(8) C8 0.0239(8) 0.0435(10) 0.0213(7) -0.0107(7) -0.0060(6) -0.0128(7) C13 0.0505(13) 0.0855(18) 0.0252(9) -0.0162(10) -0.0071(8) -0.0437(13) O1 0.0161(5) 0.0254(5) 0.0223(5) -0.0087(4) -0.0038(4) -0.0062(4) C4 0.0158(6) 0.0197(7) 0.0235(7) -0.0072(5) -0.0076(5) -0.0017(5) C3 0.0168(6) 0.0196(7) 0.0268(7) -0.0105(6) -0.0071(5) -0.0005(5) C2 0.0176(6) 0.0167(6) 0.0224(7) -0.0079(5) -0.0059(5) -0.0025(5) N4 0.0149(5) 0.0157(5) 0.0183(6) -0.0051(4) -0.0052(4) -0.0037(4) C18 0.0166(6) 0.0154(6) 0.0176(6) -0.0048(5) -0.0044(5) -0.0049(5) C17 0.0160(6) 0.0154(6) 0.0195(6) -0.0049(5) -0.0051(5) -0.0042(5) N5 0.0263(6) 0.0144(5) 0.0208(6) -0.0034(5) -0.0088(5) -0.0075(5) C19 0.0145(6) 0.0160(6) 0.0198(6) -0.0075(5) -0.0021(5) -0.0040(5) N6 0.0246(6) 0.0139(5) 0.0216(6) -0.0043(5) -0.0084(5) -0.0057(5) C20 0.0185(6) 0.0163(6) 0.0196(6) -0.0055(5) -0.0037(5) -0.0061(5) C25 0.0226(7) 0.0159(6) 0.0251(7) -0.0055(5) -0.0067(6) -0.0047(5) C24 0.0237(7) 0.0207(7) 0.0242(7) -0.0030(6) -0.0077(6) -0.0070(6) C23 0.0241(7) 0.0275(8) 0.0214(7) -0.0078(6) -0.0044(6) -0.0113(6) C22 0.0270(8) 0.0221(7) 0.0296(8) -0.0130(6) -0.0060(6) -0.0067(6) C21 0.0241(7) 0.0161(6) 0.0281(8) -0.0077(6) -0.0081(6) -0.0038(5) C26 0.0364(10) 0.0404(10) 0.0292(9) -0.0122(8) -0.0112(7) -0.0137(8) O2 0.0251(5) 0.0161(5) 0.0220(5) -0.0034(4) -0.0074(4) -0.0076(4) C16 0.0256(7) 0.0181(6) 0.0197(7) -0.0018(5) -0.0076(6) -0.0073(6) C15 0.0285(8) 0.0220(7) 0.0185(7) -0.0038(6) -0.0085(6) -0.0084(6) C14 0.0214(7) 0.0197(7) 0.0196(7) -0.0056(5) -0.0076(5) -0.0059(5) O3 0.0170(5) 0.0192(5) 0.0212(5) -0.0092(4) -0.0023(4) -0.0057(4) N7 0.0231(6) 0.0163(6) 0.0217(6) -0.0057(5) -0.0026(5) -0.0050(5) O5 0.0469(8) 0.0170(5) 0.0321(7) -0.0107(5) -0.0135(6) -0.0031(5) O6 0.0245(6) 0.0167(5) 0.0249(6) -0.0026(4) -0.0040(4) -0.0025(4) O4 0.0272(6) 0.0195(5) 0.0254(6) -0.0075(4) -0.0081(5) -0.0038(4) O7 0.0283(7) 0.0465(8) 0.0388(8) -0.0122(6) -0.0139(6) -0.0027(6) C27 0.0348(10) 0.0409(11) 0.0397(11) -0.0051(9) -0.0078(8) -0.0028(9) _refine_ls_extinction_coef 10(3) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Co1 . O3 . 2.0929(11) yes Co1 . N4 . 2.1747(12) yes Co1 . N1 . 2.1968(12) yes Co1 . O3 2_766 2.0929(11) yes Co1 . N4 2_766 2.1747(12) yes Co1 . N1 2_766 2.1968(12) yes N1 . C2 . 1.3478(18) yes N1 . C1 . 1.3439(17) yes C1 . H11 . 1.000 no C1 . C5 . 1.4009(19) yes C5 . C4 . 1.397(2) yes C5 . N2 . 1.3982(18) yes N2 . H22 . 1.000 no N2 . C6 . 1.3837(18) yes C6 . O1 . 1.2339(19) yes C6 . N3 . 1.3594(19) yes N3 . H32 . 1.000 no N3 . C7 . 1.4168(18) yes C7 . C8 . 1.393(2) yes C7 . C12 . 1.398(2) yes C12 . H121 . 1.000 no C12 . C11 . 1.391(2) yes C11 . H111 . 1.000 no C11 . C10 . 1.390(3) yes C10 . C13 . 1.512(2) yes C10 . C9 . 1.385(3) yes C9 . H91 . 1.000 no C9 . C8 . 1.397(2) yes C8 . H81 . 1.000 no C13 . H133 . 1.000 no C13 . H132 . 1.000 no C13 . H131 . 1.000 no C4 . H41 . 1.000 no C4 . C3 . 1.388(2) yes C3 . H31 . 1.000 no C3 . C2 . 1.385(2) yes C2 . H21 . 1.000 no N4 . C14 . 1.3410(19) yes N4 . C18 . 1.3476(17) yes C18 . H181 . 1.000 no C18 . C17 . 1.402(2) yes C17 . C16 . 1.396(2) yes C17 . N5 . 1.3984(18) yes N5 . H51 . 1.000 no N5 . C19 . 1.3863(19) yes C19 . O2 . 1.2232(18) yes C19 . N6 . 1.3669(18) yes N6 . H61 . 1.000 no N6 . C20 . 1.4140(18) yes C20 . C21 . 1.397(2) yes C20 . C25 . 1.397(2) yes C25 . H251 . 1.000 no C25 . C24 . 1.393(2) yes C24 . H241 . 1.000 no C24 . C23 . 1.392(2) yes C23 . C26 . 1.512(2) yes C23 . C22 . 1.395(2) yes C22 . H221 . 1.000 no C22 . C21 . 1.390(2) yes C21 . H211 . 1.000 no C26 . H263 . 1.000 no C26 . H262 . 1.000 no C26 . H261 . 1.000 no C16 . H161 . 1.000 no C16 . C15 . 1.388(2) yes C15 . H151 . 1.000 no C15 . C14 . 1.388(2) yes C14 . H141 . 1.000 no N7 . O4 . 1.2647(18) yes N7 . O6 . 1.2474(18) yes N7 . O5 . 1.2514(17) yes O7 . H5 . 0.796 no O7 . C27 . 1.411(3) yes C27 . H273 . 1.000 no C27 . H272 . 1.000 no C27 . H271 . 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 . Co1 . N4 . 88.33(4) yes O3 . Co1 . N1 . 90.23(4) yes N4 . Co1 . N1 . 90.35(4) yes O3 . Co1 . O3 2_766 179.995 yes N4 . Co1 . O3 2_766 91.67(4) yes N1 . Co1 . O3 2_766 89.77(4) yes O3 . Co1 . N4 2_766 91.67(4) yes N4 . Co1 . N4 2_766 179.995 yes N1 . Co1 . N4 2_766 89.65(4) yes O3 2_766 Co1 . N4 2_766 88.33(4) yes O3 . Co1 . N1 2_766 89.77(4) yes N4 . Co1 . N1 2_766 89.65(4) yes N1 . Co1 . N1 2_766 179.995 yes O3 2_766 Co1 . N1 2_766 90.23(4) yes N4 2_766 Co1 . N1 2_766 90.35(4) yes C2 . N1 . C1 . 117.49(12) yes C2 . N1 . Co1 . 120.12(9) yes C1 . N1 . Co1 . 122.38(10) yes H11 . C1 . C5 . 118.094 no H11 . C1 . N1 . 118.090 no C5 . C1 . N1 . 123.82(13) yes C4 . C5 . N2 . 125.56(13) yes C4 . C5 . C1 . 118.05(13) yes N2 . C5 . C1 . 116.36(13) yes H22 . N2 . C6 . 117.027 no H22 . N2 . C5 . 117.096 no C6 . N2 . C5 . 125.88(13) yes O1 . C6 . N3 . 124.50(13) yes O1 . C6 . N2 . 122.20(13) yes N3 . C6 . N2 . 113.30(13) yes H32 . N3 . C7 . 116.498 no H32 . N3 . C6 . 116.537 no C7 . N3 . C6 . 126.97(13) yes C8 . C7 . C12 . 118.96(14) yes C8 . C7 . N3 . 124.82(14) yes C12 . C7 . N3 . 116.21(14) yes H121 . C12 . C11 . 119.705 no H121 . C12 . C7 . 119.763 no C11 . C12 . C7 . 120.53(16) yes H111 . C11 . C10 . 119.489 no H111 . C11 . C12 . 119.397 no C10 . C11 . C12 . 121.11(17) yes C13 . C10 . C9 . 120.67(19) yes C13 . C10 . C11 . 121.63(19) yes C9 . C10 . C11 . 117.71(15) yes H91 . C9 . C8 . 118.757 no H91 . C9 . C10 . 118.859 no C8 . C9 . C10 . 122.38(18) yes H81 . C8 . C7 . 120.367 no H81 . C8 . C9 . 120.382 no C7 . C8 . C9 . 119.25(17) yes H133 . C13 . H132 . 109.475 no H133 . C13 . H131 . 109.476 no H132 . C13 . H131 . 109.477 no H133 . C13 . C10 . 109.535 no H132 . C13 . C10 . 109.348 no H131 . C13 . C10 . 109.517 no H41 . C4 . C3 . 121.054 no H41 . C4 . C5 . 121.057 no C3 . C4 . C5 . 117.89(13) yes H31 . C3 . C2 . 119.700 no H31 . C3 . C4 . 119.724 no C2 . C3 . C4 . 120.58(14) yes H21 . C2 . N1 . 118.895 no H21 . C2 . C3 . 118.944 no N1 . C2 . C3 . 122.16(13) yes C14 . N4 . C18 . 118.78(12) yes C14 . N4 . Co1 . 119.90(10) yes C18 . N4 . Co1 . 121.30(10) yes H181 . C18 . C17 . 118.664 no H181 . C18 . N4 . 118.650 no C17 . C18 . N4 . 122.69(13) yes C16 . C17 . N5 . 118.63(13) yes C16 . C17 . C18 . 117.82(13) yes N5 . C17 . C18 . 123.54(13) yes H51 . N5 . C19 . 117.082 no H51 . N5 . C17 . 117.030 no C19 . N5 . C17 . 125.89(13) yes O2 . C19 . N6 . 124.40(14) yes O2 . C19 . N5 . 123.25(13) yes N6 . C19 . N5 . 112.34(13) yes H61 . N6 . C20 . 117.411 no H61 . N6 . C19 . 117.462 no C20 . N6 . C19 . 125.13(13) yes C21 . C20 . C25 . 118.89(14) yes C21 . C20 . N6 . 117.68(14) yes C25 . C20 . N6 . 123.38(13) yes H251 . C25 . C24 . 120.118 no H251 . C25 . C20 . 120.057 no C24 . C25 . C20 . 119.83(14) yes H241 . C24 . C23 . 119.065 no H241 . C24 . C25 . 119.070 no C23 . C24 . C25 . 121.86(15) yes C26 . C23 . C22 . 121.45(15) yes C26 . C23 . C24 . 120.92(16) yes C22 . C23 . C24 . 117.61(15) yes H221 . C22 . C21 . 119.311 no H221 . C22 . C23 . 119.291 no C21 . C22 . C23 . 121.40(15) yes H211 . C21 . C22 . 119.776 no H211 . C21 . C20 . 119.856 no C22 . C21 . C20 . 120.37(15) yes H263 . C26 . H262 . 109.476 no H263 . C26 . H261 . 109.476 no H262 . C26 . H261 . 109.476 no H263 . C26 . C23 . 109.527 no H262 . C26 . C23 . 109.370 no H261 . C26 . C23 . 109.504 no H161 . C16 . C15 . 120.427 no H161 . C16 . C17 . 120.392 no C15 . C16 . C17 . 119.18(14) yes H151 . C15 . C14 . 120.315 no H151 . C15 . C16 . 120.260 no C14 . C15 . C16 . 119.42(14) yes H141 . C14 . N4 . 118.961 no H141 . C14 . C15 . 118.935 no N4 . C14 . C15 . 122.10(13) yes O4 . N7 . O6 . 119.99(13) yes O4 . N7 . O5 . 119.77(13) yes O6 . N7 . O5 . 120.24(14) yes H5 . O7 . C27 . 110.181 no H273 . C27 . H272 . 109.476 no H273 . C27 . H271 . 109.475 no H272 . C27 . H271 . 109.476 no H273 . C27 . O7 . 109.383 no H272 . C27 . O7 . 109.474 no H271 . C27 . O7 . 109.543 no # Attachment 'NiTUP.CIF' data_NiTUP.cif _database_code_depnum_ccdc_archive 'CCDC 285686' _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment mixed #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 8.8731(12) _cell_angle_alpha 71.814(3) _cell_length_b 12.7159(18) _cell_angle_beta 76.228(3) _cell_length_c 13.7082(19) _cell_angle_gamma 74.062(3) _cell_volume 1393.2(3) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'Ni ' 0.3393 1.1124 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421 1.0341 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 1 _chemical_formula_sum ' C54 H64 N14 Ni1 O14 ' _chemical_formula_moiety ' C54 H64 N14 Ni1 O14 ' _chemical_compound_source ; ? ; _chemical_formula_weight 1191.88 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 120 _exptl_crystal_description ' irregular ' _exptl_crystal_colour ? _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 626 _exptl_absorpt_coefficient_mu 0.428 _diffrn_measurement_device_type ; Unknown ; _diffrn_radiation_monochromator graphite _computing_data_collection ; DATA COLLECTION ; _computing_data_reduction ; USER DEFINED 5 ; _computing_cell_refinement ; USER DEFINED 6 ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method \w/2\q _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.94 # Sheldrick geometric definitions 0.92 0.94 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 120 _diffrn_reflns_number 15884 _reflns_number_total 6870 _diffrn_reflns_av_R_equivalents 0.07 # Number of reflections with Friedels Law is 6870 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 6908 _diffrn_reflns_theta_min 1.586 _diffrn_reflns_theta_max 28.281 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.432 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -15 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _refine_diff_density_min -0.59 _refine_diff_density_max 0.71 _refine_ls_number_reflns 2593 _refine_ls_number_restraints 0 _refine_ls_number_parameters 376 #_refine_ls_R_factor_ref 0.0795 _refine_ls_wR_factor_ref 0.1516 _refine_ls_goodness_of_fit_ref 0.9412 #_reflns_number_all 6846 _refine_ls_R_factor_all 0.2194 _refine_ls_wR_factor_all 0.2113 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.50u(I) _reflns_number_gt 2593 _refine_ls_R_factor_gt 0.0795 _refine_ls_wR_factor_gt 0.1516 _refine_ls_shift/su_max 0.000134 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 5.95 6.64 3.41 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; User-defined data collection reference Spare 5 Spare 6 Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group _atom_site_attached_hydrogens Ni1 Ni 1.0000 0.5000 1.0000 0.0078 1.0000 Uani S . . . . . N1 N 1.2119(7) 0.4626(5) 1.0641(5) 0.0143 1.0000 Uani . . . . . . C3 C 1.2292(9) 0.5190(7) 1.1280(6) 0.0126 1.0000 Uani . . . . . . C4 C 1.3681(9) 0.4980(6) 1.1688(6) 0.0132 1.0000 Uani . . . . . . C5 C 1.4979(9) 0.4135(6) 1.1419(6) 0.0154 1.0000 Uani . . . . . . C6 C 1.4801(10) 0.3562(7) 1.0768(6) 0.0173 1.0000 Uani . . . . . . C7 C 1.3384(10) 0.3816(7) 1.0392(6) 0.0170 1.0000 Uani . . . . . . N2 N 1.3638(8) 0.5634(6) 1.2354(5) 0.0169 1.0000 Uani . . . . . . C9 C 1.4880(10) 0.5596(7) 1.2819(6) 0.0161 1.0000 Uani . . . . . . N3 N 1.4418(8) 0.6157(6) 1.3582(5) 0.0193 1.0000 Uani . . . . . . C11 C 1.5424(10) 0.6272(7) 1.4195(7) 0.0210 1.0000 Uani . . . . . . C12 C 1.7056(10) 0.5982(8) 1.4028(7) 0.0268 1.0000 Uani . . . . . . C13 C 1.7902(12) 0.6168(9) 1.4668(7) 0.0344 1.0000 Uani . . . . . . C14 C 1.7121(12) 0.6678(8) 1.5474(6) 0.0296 1.0000 Uani . . . . . . C15 C 1.5504(11) 0.6939(7) 1.5636(6) 0.0247 1.0000 Uani . . . . . . C16 C 1.4667(10) 0.6749(7) 1.5017(7) 0.0216 1.0000 Uani . . . . . . C17 C 1.8101(13) 0.6936(11) 1.6116(8) 0.0493 1.0000 Uani . . . . . . O1 O 1.6257(6) 0.5100(5) 1.2564(4) 0.0182 1.0000 Uani . . . . . . N4 N 0.9475(8) 0.3444(5) 1.1019(5) 0.0172 1.0000 Uani . . . . . . C20 C 0.9064(9) 0.2712(6) 1.0653(6) 0.0188 1.0000 Uani . . . . . . C21 C 0.8740(9) 0.1673(7) 1.1289(6) 0.0183 1.0000 Uani . . . . . . C22 C 0.8860(10) 0.1419(7) 1.2328(6) 0.0210 1.0000 Uani . . . . . . C23 C 0.9259(10) 0.2178(6) 1.2712(6) 0.0219 1.0000 Uani . . . . . . C24 C 0.9560(9) 0.3198(7) 1.2025(6) 0.0182 1.0000 Uani . . . . . . N5 N 0.8327(9) 0.0888(5) 1.0941(5) 0.0205 1.0000 Uani . . . . . . C26 C 0.7770(10) 0.1119(7) 1.0002(6) 0.0196 1.0000 Uani . . . . . . N6 N 0.7402(8) 0.0188(5) 0.9904(5) 0.0173 1.0000 Uani . . . . . . C28 C 0.6719(9) 0.0194(7) 0.9068(6) 0.0170 1.0000 Uani . . . . . . C29 C 0.6973(10) -0.0838(7) 0.8819(6) 0.0193 1.0000 Uani . . . . . . C30 C 0.6333(10) -0.0902(7) 0.8019(7) 0.0219 1.0000 Uani . . . . . . C31 C 0.5390(10) 0.0045(7) 0.7455(7) 0.0215 1.0000 Uani . . . . . . C32 C 0.5114(10) 0.1078(7) 0.7704(7) 0.0245 1.0000 Uani . . . . . . C33 C 0.5773(10) 0.1141(7) 0.8504(6) 0.0207 1.0000 Uani . . . . . . C34 C 0.4759(12) 0.0000(8) 0.6534(7) 0.0336 1.0000 Uani . . . . . . O2 O 0.7597(7) 0.2059(4) 0.9392(4) 0.0201 1.0000 Uani . . . . . . O3 O 1.1249(6) 0.4207(5) 0.8826(4) 0.0175 1.0000 Uani . . . . . . N7 N 1.0700(8) 0.2147(6) 0.7900(6) 0.0224 1.0000 Uani . . . . . . O4 O 0.9910(7) 0.3071(4) 0.7457(4) 0.0212 1.0000 Uani . . . . . . O5 O 1.1353(7) 0.2103(5) 0.8647(4) 0.0225 1.0000 Uani . . . . . . O6 O 1.0885(8) 0.1289(5) 0.7608(5) 0.0294 1.0000 Uani . . . . . . O7 O 0.8701(8) 0.2379(6) 0.5988(5) 0.0404 1.0000 Uani . . . . . . C35 C 0.8839(14) 0.1251(10) 0.5978(10) 0.0549 1.0000 Uani . . . . . . H31 H 1.1368(9) 0.5783(7) 1.1482(6) 0.0202 1.0000 Uiso R . . . . . H51 H 1.5995(9) 0.3972(6) 1.1689(6) 0.0200 1.0000 Uiso R . . . . . H61 H 1.5695(10) 0.2945(7) 1.0579(6) 0.0252 1.0000 Uiso R . . . . . H71 H 1.3299(10) 0.3395(7) 0.9908(6) 0.0213 1.0000 Uiso R . . . . . H121 H 1.7633(10) 0.5623(8) 1.3451(7) 0.0339 1.0000 Uiso R . . . . . H131 H 1.9090(12) 0.5954(9) 1.4542(7) 0.0466 1.0000 Uiso R . . . . . H151 H 1.4924(11) 0.7291(7) 1.6217(6) 0.0363 1.0000 Uiso R . . . . . H161 H 1.3479(10) 0.6950(7) 1.5158(7) 0.0290 1.0000 Uiso R . . . . . H171 H 1.7365(13) 0.7285(11) 1.6662(8) 0.0719 1.0000 Uiso R . . . . . H172 H 1.8803(13) 0.6218(11) 1.6457(8) 0.0719 1.0000 Uiso R . . . . . H173 H 1.8770(13) 0.7476(11) 1.5651(8) 0.0719 1.0000 Uiso R . . . . . H201 H 0.8990(9) 0.2920(6) 0.9897(6) 0.0219 1.0000 Uiso R . . . . . H221 H 0.8660(10) 0.0680(7) 1.2810(6) 0.0275 1.0000 Uiso R . . . . . H231 H 0.9335(10) 0.1999(6) 1.3465(6) 0.0286 1.0000 Uiso R . . . . . H241 H 0.9843(9) 0.3754(7) 1.2292(6) 0.0220 1.0000 Uiso R . . . . . H291 H 0.7634(10) -0.1534(7) 0.9225(6) 0.0247 1.0000 Uiso R . . . . . H301 H 0.6550(10) -0.1644(7) 0.7847(7) 0.0289 1.0000 Uiso R . . . . . H321 H 0.4428(10) 0.1769(7) 0.7312(7) 0.0300 1.0000 Uiso R . . . . . H331 H 0.5588(10) 0.1885(7) 0.8666(6) 0.0278 1.0000 Uiso R . . . . . H341 H 0.4111(12) 0.0761(8) 0.6229(7) 0.0504 1.0000 Uiso R . . . . . H342 H 0.5674(12) -0.0219(8) 0.5996(7) 0.0504 1.0000 Uiso R . . . . . H343 H 0.4083(12) -0.0575(8) 0.6773(7) 0.0504 1.0000 Uiso R . . . . . H251 H 0.8432 0.0090 1.1403 0.0278 1.0000 Uiso . . . . . . H271 H 0.7630 -0.0548 1.0456 0.0248 1.0000 Uiso . . . . . . H81 H 1.2610 0.6194 1.2497 0.0231 1.0000 Uiso . . . . . . H101 H 1.3252 0.6524 1.3725 0.0262 1.0000 Uiso . . . . . . H32 H 0.9668 0.2972 0.5450 0.0500 1.0000 Uiso . . . . . . H421 H 0.7934 0.0933 0.6467 0.0666 1.0000 Uiso . . . . . . H422 H 0.9867 0.0754 0.6199 0.0666 1.0000 Uiso . . . . . . H423 H 0.8826 0.1208 0.5257 0.0666 1.0000 Uiso . . . . . . 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 Ni1 0.0091(10) 0.0100(9) 0.0077(10) -0.0047(8) -0.0023(8) -0.0041(8) N1 0.010(3) 0.016(3) 0.020(4) -0.008(3) 0.000(3) -0.005(3) C3 0.015(4) 0.013(4) 0.012(4) -0.003(3) -0.002(3) -0.006(3) C4 0.013(4) 0.018(4) 0.016(4) -0.009(3) -0.009(3) -0.004(3) C5 0.007(4) 0.014(4) 0.025(5) -0.003(3) -0.007(3) -0.002(3) C6 0.020(4) 0.014(4) 0.021(4) -0.014(3) -0.005(4) 0.004(3) C7 0.023(4) 0.015(4) 0.017(4) -0.006(3) -0.005(3) -0.005(4) N2 0.013(4) 0.021(4) 0.018(4) -0.009(3) -0.005(3) 0.000(3) C9 0.016(5) 0.017(4) 0.016(4) -0.001(3) -0.004(3) -0.007(3) N3 0.014(4) 0.023(4) 0.026(4) -0.007(3) -0.013(3) -0.004(3) C11 0.022(5) 0.023(5) 0.025(5) -0.009(4) -0.009(4) -0.009(4) C12 0.020(5) 0.044(6) 0.022(5) -0.011(4) -0.008(4) -0.010(4) C13 0.033(6) 0.057(7) 0.020(5) -0.009(5) -0.013(4) -0.015(5) C14 0.040(6) 0.045(6) 0.009(4) 0.002(4) -0.006(4) -0.028(5) C15 0.043(6) 0.032(5) 0.006(4) -0.005(4) -0.001(4) -0.020(4) C16 0.022(5) 0.019(4) 0.024(5) -0.005(4) -0.004(4) -0.004(4) C17 0.049(7) 0.092(9) 0.024(5) -0.008(6) -0.011(5) -0.047(7) O1 0.015(3) 0.029(3) 0.015(3) -0.005(3) -0.006(2) -0.010(3) N4 0.019(4) 0.014(3) 0.022(4) -0.002(3) -0.013(3) -0.005(3) C20 0.021(4) 0.013(4) 0.024(5) -0.005(4) -0.004(4) -0.007(4) C21 0.011(4) 0.016(4) 0.030(5) -0.009(4) -0.008(3) 0.001(3) C22 0.031(5) 0.019(4) 0.014(4) 0.006(3) -0.009(4) -0.014(4) C23 0.035(5) 0.011(4) 0.020(4) 0.000(3) -0.009(4) -0.006(4) C24 0.015(4) 0.017(4) 0.024(5) -0.003(4) -0.012(4) 0.000(3) N5 0.037(4) 0.010(3) 0.021(4) -0.003(3) -0.013(3) -0.008(3) C26 0.022(5) 0.013(4) 0.022(4) -0.006(4) 0.004(4) -0.006(3) N6 0.023(4) 0.017(3) 0.018(4) -0.005(3) -0.009(3) -0.009(3) C28 0.019(4) 0.018(4) 0.017(4) -0.010(3) -0.001(3) -0.004(3) C29 0.018(4) 0.014(4) 0.025(5) -0.004(4) -0.004(3) -0.002(3) C30 0.020(4) 0.025(5) 0.025(5) -0.010(4) -0.005(4) -0.006(4) C31 0.016(4) 0.029(5) 0.026(5) -0.009(4) -0.005(4) -0.013(4) C32 0.020(5) 0.025(5) 0.029(5) -0.001(4) -0.015(4) -0.005(4) C33 0.024(5) 0.014(4) 0.022(5) -0.002(4) -0.008(4) -0.002(4) C34 0.045(6) 0.039(6) 0.025(5) -0.010(4) -0.008(4) -0.021(5) O2 0.029(3) 0.015(3) 0.017(3) 0.002(2) -0.014(3) -0.004(3) O3 0.017(3) 0.020(3) 0.018(3) -0.007(2) -0.004(2) -0.006(2) N7 0.029(4) 0.014(4) 0.028(4) -0.012(3) -0.004(3) -0.002(3) O4 0.027(3) 0.012(3) 0.020(3) -0.001(2) -0.001(3) -0.003(3) O5 0.029(3) 0.017(3) 0.025(3) -0.008(3) -0.008(3) -0.006(3) O6 0.050(4) 0.015(3) 0.028(3) -0.010(3) -0.018(3) 0.001(3) O7 0.033(4) 0.045(4) 0.041(4) -0.009(4) -0.015(3) -0.002(3) C35 0.051(8) 0.050(7) 0.060(8) 0.005(6) -0.028(6) -0.014(6) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 . O3 . 2.094(5) yes Ni1 . N4 . 2.134(6) yes Ni1 . N1 . 2.137(6) yes Ni1 . O3 2_767 2.094(5) yes Ni1 . N4 2_767 2.134(6) yes Ni1 . N1 2_767 2.137(6) yes N1 . C7 . 1.356(10) yes N1 . C3 . 1.351(9) yes C3 . H31 . 1.000 no C3 . C4 . 1.399(10) yes C4 . N2 . 1.402(9) yes C4 . C5 . 1.407(11) yes C5 . H51 . 1.000 no C5 . C6 . 1.375(11) yes C6 . H61 . 1.000 no C6 . C7 . 1.390(11) yes C7 . H71 . 1.000 no N2 . H81 . 1.011 no N2 . C9 . 1.381(10) yes C9 . O1 . 1.235(9) yes C9 . N3 . 1.369(10) yes N3 . H101 . 1.011 no N3 . C11 . 1.424(10) yes C11 . C16 . 1.390(11) yes C11 . C12 . 1.374(12) yes C12 . H121 . 1.000 no C12 . C13 . 1.389(12) yes C13 . H131 . 1.000 no C13 . C14 . 1.398(13) yes C14 . C17 . 1.531(12) yes C14 . C15 . 1.360(13) yes C15 . H151 . 1.000 no C15 . C16 . 1.362(11) yes C16 . H161 . 1.000 no C17 . H173 . 1.000 no C17 . H172 . 1.000 no C17 . H171 . 1.000 no N4 . C24 . 1.332(10) yes N4 . C20 . 1.347(10) yes C20 . H201 . 1.000 no C20 . C21 . 1.400(10) yes C21 . N5 . 1.393(10) yes C21 . C22 . 1.382(11) yes C22 . H221 . 1.000 no C22 . C23 . 1.388(11) yes C23 . H231 . 1.000 no C23 . C24 . 1.396(11) yes C24 . H241 . 1.000 no N5 . H251 . 1.008 no N5 . C26 . 1.405(10) yes C26 . O2 . 1.220(9) yes C26 . N6 . 1.363(10) yes N6 . H271 . 1.007 no N6 . C28 . 1.416(10) yes C28 . C33 . 1.388(11) yes C28 . C29 . 1.403(11) yes C29 . H291 . 1.000 no C29 . C30 . 1.382(11) yes C30 . H301 . 1.000 no C30 . C31 . 1.387(12) yes C31 . C34 . 1.519(12) yes C31 . C32 . 1.401(12) yes C32 . H321 . 1.000 no C32 . C33 . 1.391(11) yes C33 . H331 . 1.000 no C34 . H343 . 1.000 no C34 . H342 . 1.000 no C34 . H341 . 1.000 no N7 . O6 . 1.234(8) yes N7 . O5 . 1.271(9) yes N7 . O4 . 1.243(8) yes O7 . H32 . 1.248 no O7 . C35 . 1.410(14) yes C35 . H423 . 1.010 no C35 . H422 . 1.010 no C35 . H421 . 1.006 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 . Ni1 . N4 . 91.8(2) yes O3 . Ni1 . N1 . 90.5(2) yes N4 . Ni1 . N1 . 88.6(2) yes O3 . Ni1 . O3 2_767 179.995 yes N4 . Ni1 . O3 2_767 88.2(2) yes N1 . Ni1 . O3 2_767 89.5(2) yes O3 . Ni1 . N4 2_767 88.2(2) yes N4 . Ni1 . N4 2_767 179.995 yes N1 . Ni1 . N4 2_767 91.4(2) yes O3 2_767 Ni1 . N4 2_767 91.8(2) yes O3 . Ni1 . N1 2_767 89.5(2) yes N4 . Ni1 . N1 2_767 91.4(2) yes N1 . Ni1 . N1 2_767 179.995 yes O3 2_767 Ni1 . N1 2_767 90.5(2) yes N4 2_767 Ni1 . N1 2_767 88.6(2) yes C7 . N1 . C3 . 116.8(7) yes C7 . N1 . Ni1 . 120.5(5) yes C3 . N1 . Ni1 . 122.7(5) yes H31 . C3 . C4 . 118.166 no H31 . C3 . N1 . 118.112 no C4 . C3 . N1 . 123.7(7) yes N2 . C4 . C5 . 125.6(6) yes N2 . C4 . C3 . 115.9(7) yes C5 . C4 . C3 . 118.5(7) yes H51 . C5 . C6 . 121.746 no H51 . C5 . C4 . 120.588 no C6 . C5 . C4 . 117.7(7) yes H61 . C6 . C7 . 120.068 no H61 . C6 . C5 . 119.204 no C7 . C6 . C5 . 120.7(7) yes H71 . C7 . N1 . 118.569 no H71 . C7 . C6 . 118.802 no N1 . C7 . C6 . 122.6(7) yes H81 . N2 . C9 . 117.047 no H81 . N2 . C4 . 117.027 no C9 . N2 . C4 . 125.9(7) yes O1 . C9 . N3 . 124.3(7) yes O1 . C9 . N2 . 122.7(7) yes N3 . C9 . N2 . 113.1(7) yes H101 . N3 . C11 . 116.969 no H101 . N3 . C9 . 116.841 no C11 . N3 . C9 . 126.2(7) yes C16 . C11 . C12 . 117.9(8) yes C16 . C11 . N3 . 116.2(7) yes C12 . C11 . N3 . 125.9(8) yes H121 . C12 . C13 . 120.100 no H121 . C12 . C11 . 119.653 no C13 . C12 . C11 . 120.2(9) yes H131 . C13 . C14 . 119.145 no H131 . C13 . C12 . 119.800 no C14 . C13 . C12 . 121.0(9) yes C17 . C14 . C15 . 123.0(9) yes C17 . C14 . C13 . 119.3(9) yes C15 . C14 . C13 . 117.7(8) yes H151 . C15 . C16 . 119.669 no H151 . C15 . C14 . 118.803 no C16 . C15 . C14 . 121.5(8) yes H161 . C16 . C15 . 119.575 no H161 . C16 . C11 . 118.815 no C15 . C16 . C11 . 121.6(8) yes H173 . C17 . H172 . 109.475 no H173 . C17 . H171 . 109.475 no H172 . C17 . H171 . 109.477 no H173 . C17 . C14 . 109.574 no H172 . C17 . C14 . 109.711 no H171 . C17 . C14 . 109.114 no C24 . N4 . C20 . 120.0(7) yes C24 . N4 . Ni1 . 119.3(5) yes C20 . N4 . Ni1 . 120.7(5) yes H201 . C20 . C21 . 118.804 no H201 . C20 . N4 . 118.601 no C21 . C20 . N4 . 122.6(7) yes N5 . C21 . C22 . 118.8(7) yes N5 . C21 . C20 . 124.4(7) yes C22 . C21 . C20 . 116.8(7) yes H221 . C22 . C23 . 119.478 no H221 . C22 . C21 . 119.707 no C23 . C22 . C21 . 120.8(7) yes H231 . C23 . C24 . 120.381 no H231 . C23 . C22 . 120.917 no C24 . C23 . C22 . 118.7(7) yes H241 . C24 . N4 . 119.392 no H241 . C24 . C23 . 119.545 no N4 . C24 . C23 . 121.1(7) yes H251 . N5 . C26 . 117.358 no H251 . N5 . C21 . 117.188 no C26 . N5 . C21 . 125.5(6) yes O2 . C26 . N6 . 126.1(8) yes O2 . C26 . N5 . 122.3(7) yes N6 . C26 . N5 . 111.5(7) yes H271 . N6 . C28 . 117.967 no H271 . N6 . C26 . 118.320 no C28 . N6 . C26 . 123.7(7) yes C33 . C28 . C29 . 118.0(7) yes C33 . C28 . N6 . 124.4(7) yes C29 . C28 . N6 . 117.6(7) yes H291 . C29 . C30 . 119.776 no H291 . C29 . C28 . 119.241 no C30 . C29 . C28 . 121.0(8) yes H301 . C30 . C31 . 119.511 no H301 . C30 . C29 . 119.523 no C31 . C30 . C29 . 121.0(8) yes C34 . C31 . C32 . 119.9(8) yes C34 . C31 . C30 . 121.4(8) yes C32 . C31 . C30 . 118.5(7) yes H321 . C32 . C33 . 119.843 no H321 . C32 . C31 . 119.834 no C33 . C32 . C31 . 120.3(8) yes H331 . C33 . C28 . 119.102 no H331 . C33 . C32 . 119.699 no C28 . C33 . C32 . 121.2(8) yes H343 . C34 . H342 . 109.476 no H343 . C34 . H341 . 109.476 no H342 . C34 . H341 . 109.476 no H343 . C34 . C31 . 109.473 no H342 . C34 . C31 . 109.270 no H341 . C34 . C31 . 109.656 no O6 . N7 . O5 . 120.1(7) yes O6 . N7 . O4 . 120.9(7) yes O5 . N7 . O4 . 118.9(6) yes H32 . O7 . C35 . 123.728 no H423 . C35 . H422 . 107.918 no H423 . C35 . H421 . 108.226 no H422 . C35 . H421 . 108.266 no H423 . C35 . O7 . 110.899 no H422 . C35 . O7 . 110.808 no H421 . C35 . O7 . 110.618 no