# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_3Sm _database_code_depnum_ccdc_archive 'CCDC 746889' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 Co3 N8 O32 Sm2' _chemical_formula_weight 1614.23 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.446(2) _cell_length_b 7.5939(15) _cell_length_c 30.513(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.00(3) _cell_angle_gamma 90.00 _cell_volume 2390.7(8) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 17074 _cell_measurement_theta_min 3.005 _cell_measurement_theta_max 25.575 _exptl_crystal_description Sheet _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.242 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1578 _exptl_absorpt_coefficient_mu 3.556 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5365 _exptl_absorpt_correction_T_max 0.5365 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22238 _diffrn_reflns_av_R_equivalents 0.0917 _diffrn_reflns_av_sigmaI/netI 0.0787 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5467 _reflns_number_gt 4506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0600P)^2^+22.9776P] 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 5467 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1436 _refine_ls_wR_factor_gt 0.1365 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _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 0.8947(4) 0.5694(6) 0.07699(14) 0.0200(10) Uani 1 1 d . . . C2 C 0.7897(4) 0.4709(7) 0.04494(15) 0.0226(11) Uani 1 1 d . . . C3 C 0.4457(4) 0.3535(6) 0.13995(13) 0.0151(9) Uani 1 1 d . . . C4 C 0.3272(4) 0.2483(6) 0.12199(13) 0.0164(9) Uani 1 1 d . . . C5 C 0.2365(4) 0.3294(6) 0.09040(15) 0.0200(10) Uani 1 1 d . . . H5 H 0.2446 0.4492 0.0823 0.024 Uiso 1 1 calc R . . C6 C 0.1328(4) 0.2257(6) 0.07106(14) 0.0194(10) Uani 1 1 d . . . C7 C 0.1191(4) 0.0521(6) 0.08418(15) 0.0225(11) Uani 1 1 d . . . C8 C 0.2110(4) -0.0309(6) 0.11483(14) 0.0219(11) Uani 1 1 d . . . H8 H 0.2020 -0.1507 0.1228 0.026 Uiso 1 1 calc R . . C9 C 0.3162(4) 0.0685(6) 0.13336(13) 0.0170(10) Uani 1 1 d . . . C10 C 0.4148(4) -0.0105(6) 0.16814(13) 0.0183(10) Uani 1 1 d . . . C11 C -0.0452(5) 0.1282(7) 0.03416(16) 0.0280(12) Uani 1 1 d . . . H11 H -0.1248 0.1212 0.0143 0.034 Uiso 1 1 calc R . . C12 C 0.7364(4) 0.5003(5) 0.23277(14) 0.0146(9) Uani 1 1 d . . . C13 C 0.8410(4) 0.5624(6) 0.26953(13) 0.0163(9) Uani 1 1 d . . . C14 C 0.9325(4) 0.4410(6) 0.28811(14) 0.0185(10) Uani 1 1 d . . . H14 H 0.9218 0.3184 0.2824 0.022 Uiso 1 1 calc R . . C15 C 1.0409(4) 0.5072(6) 0.31553(15) 0.0194(10) Uani 1 1 d . . . C16 C 1.0595(4) 0.6881(6) 0.32441(14) 0.0188(10) Uani 1 1 d . . . C17 C 0.9640(4) 0.8079(6) 0.30739(14) 0.0182(10) Uani 1 1 d . . . H17 H 0.9732 0.9297 0.3142 0.022 Uiso 1 1 calc R . . C18 C 0.8547(4) 0.7445(6) 0.28003(14) 0.0161(9) Uani 1 1 d . . . C19 C 0.7496(4) 0.8731(6) 0.26507(14) 0.0151(9) Uani 1 1 d . . . C20 C 1.2282(5) 0.5543(7) 0.35816(18) 0.0310(13) Uani 1 1 d . . . H20 H 1.3102 0.5313 0.3755 0.037 Uiso 1 1 calc R . . Co1 Co 1.0000 0.5000 0.0000 0.01855(19) Uani 1 2 d S . . Co2 Co 0.71389(5) 0.44932(8) 0.130104(19) 0.01759(14) Uani 1 1 d . . . N1 N 0.0287(4) 0.2684(5) 0.03879(12) 0.0206(9) Uani 1 1 d . . . N2 N 0.0041(4) -0.0037(6) 0.06047(13) 0.0277(10) Uani 1 1 d . . . H2 H -0.0311 -0.1082 0.0622 0.033 Uiso 1 1 calc R . . N3 N 1.1790(3) 0.7124(5) 0.35115(12) 0.0216(9) Uani 1 1 d . . . N4 N 1.1501(4) 0.4287(6) 0.33812(15) 0.0315(11) Uani 1 1 d . . . H4 H 1.1661 0.3148 0.3392 0.038 Uiso 1 1 calc R . . O1 O 0.9906(3) 0.6300(5) 0.06092(11) 0.0244(8) Uani 1 1 d . . . O2 O 0.8035(3) 0.4639(5) 0.00460(10) 0.0258(8) Uani 1 1 d . . . O3 O 0.8782(3) 0.5835(5) 0.11622(10) 0.0250(8) Uani 1 1 d . . . O4 O 0.6996(3) 0.4068(5) 0.06133(11) 0.0304(9) Uani 1 1 d . . . O5 O 0.5454(3) 0.3173(4) 0.12360(10) 0.0208(7) Uani 1 1 d . . . O6 O 0.4346(3) 0.4760(4) 0.16630(10) 0.0203(7) Uani 1 1 d . . . O7 O 0.4179(3) -0.1757(4) 0.17132(10) 0.0242(8) Uani 1 1 d . . . O8 O 0.4911(3) 0.0911(4) 0.19219(10) 0.0214(8) Uani 1 1 d . . . O9 O 0.7529(3) 0.5419(5) 0.19489(10) 0.0262(8) Uani 1 1 d . . . O10 O 0.6406(3) 0.4124(4) 0.24198(10) 0.0196(7) Uani 1 1 d . . . O11 O 0.6356(3) 0.8167(4) 0.25036(10) 0.0187(7) Uani 1 1 d . . . O12 O 0.7702(3) 1.0358(4) 0.26936(11) 0.0221(8) Uani 1 1 d . . . O13 O 0.6082(3) 0.6957(5) 0.11508(12) 0.0322(9) Uani 1 1 d . . . H13A H 0.5816 0.7196 0.0880 0.048 Uiso 1 1 d R . . H13B H 0.5546 0.7084 0.1331 0.048 Uiso 1 1 d R . . O14 O 0.7213(8) 0.8701(10) 0.0305(3) 0.125(3) Uani 1 1 d . . . H14A H 0.7734 0.8806 0.0122 0.188 Uiso 1 1 d R . . H14B H 0.7170 0.7693 0.0427 0.188 Uiso 1 1 d R . . O15 O 0.4954(7) 0.6113(10) 0.4558(2) 0.118(3) Uani 1 1 d . . . H15A H 0.5543 0.6124 0.4785 0.178 Uiso 1 1 d R . . H15B H 0.4203 0.5782 0.4597 0.178 Uiso 1 1 d R . . O16 O 0.4269(8) 0.7246(15) 0.0361(3) 0.170(4) Uani 1 1 d . . . H16A H 0.3454 0.7087 0.0305 0.256 Uiso 1 1 d R . . H16B H 0.4700 0.7024 0.0152 0.256 Uiso 1 1 d R . . Sm1 Sm 0.449255(18) 0.63056(3) 0.231951(6) 0.01297(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0238(19) 0.018(2) 0.0182(19) 0.0031(17) 0.0046(16) 0.0007(18) C2 0.0179(18) 0.031(3) 0.019(2) 0.0021(18) 0.0038(16) 0.0016(19) C3 0.0184(17) 0.013(2) 0.0130(17) 0.0049(15) 0.0010(14) 0.0009(16) C4 0.0170(17) 0.015(2) 0.0175(18) -0.0015(16) 0.0039(14) -0.0004(17) C5 0.0221(19) 0.014(2) 0.023(2) 0.0033(17) 0.0007(16) -0.0038(17) C6 0.0191(18) 0.020(2) 0.0179(19) -0.0007(17) -0.0001(15) -0.0004(18) C7 0.025(2) 0.014(2) 0.027(2) 0.0017(18) -0.0009(17) -0.0032(19) C8 0.032(2) 0.013(2) 0.020(2) 0.0018(16) 0.0002(17) -0.0037(19) C9 0.0253(19) 0.013(2) 0.0115(17) 0.0014(15) -0.0011(15) 0.0013(17) C10 0.029(2) 0.0111(19) 0.0143(18) 0.0019(15) 0.0013(16) -0.0006(18) C11 0.028(2) 0.028(3) 0.026(2) 0.001(2) -0.0043(19) -0.004(2) C12 0.0163(17) 0.0054(17) 0.0213(19) -0.0019(15) 0.0000(15) 0.0011(16) C13 0.0131(16) 0.021(2) 0.0148(18) -0.0005(16) 0.0035(14) -0.0013(17) C14 0.0191(18) 0.0108(19) 0.025(2) 0.0011(16) 0.0010(16) 0.0019(17) C15 0.0168(18) 0.014(2) 0.026(2) 0.0035(17) 0.0003(16) 0.0051(17) C16 0.0159(17) 0.023(2) 0.0174(19) 0.0022(17) 0.0016(15) -0.0033(18) C17 0.0158(17) 0.017(2) 0.022(2) -0.0014(17) 0.0030(15) -0.0002(17) C18 0.0124(16) 0.017(2) 0.0192(19) 0.0004(16) 0.0029(14) 0.0010(16) C19 0.0124(16) 0.014(2) 0.0192(19) 0.0040(15) 0.0035(14) -0.0008(16) C20 0.022(2) 0.022(3) 0.044(3) -0.001(2) -0.012(2) -0.001(2) Co1 0.0175(3) 0.0222(4) 0.0162(4) 0.0031(3) 0.0034(3) 0.0000(3) Co2 0.0178(2) 0.0187(3) 0.0163(3) -0.0003(2) 0.0028(2) -0.0029(2) N1 0.0230(17) 0.0157(19) 0.0210(17) 0.0035(14) -0.0030(14) -0.0033(16) N2 0.0299(19) 0.021(2) 0.030(2) 0.0024(17) -0.0030(16) -0.0112(18) N3 0.0176(16) 0.020(2) 0.0246(18) 0.0017(16) -0.0060(14) 0.0004(16) N4 0.0260(19) 0.0146(19) 0.047(2) 0.0068(18) -0.0146(18) 0.0051(17) O1 0.0245(14) 0.0252(18) 0.0256(16) -0.0011(13) 0.0104(12) -0.0060(14) O2 0.0187(13) 0.038(2) 0.0206(15) 0.0027(14) 0.0017(12) 0.0000(15) O3 0.0296(15) 0.0270(18) 0.0202(15) -0.0017(13) 0.0092(12) -0.0064(14) O4 0.0248(15) 0.046(2) 0.0213(15) -0.0025(15) 0.0064(13) -0.0128(16) O5 0.0194(13) 0.0205(16) 0.0225(15) -0.0033(13) 0.0038(12) -0.0034(13) O6 0.0261(14) 0.0145(15) 0.0194(14) -0.0051(12) 0.0005(12) -0.0002(13) O7 0.0422(18) 0.0075(14) 0.0210(15) 0.0017(12) -0.0013(14) 0.0045(14) O8 0.0306(15) 0.0177(16) 0.0142(13) 0.0025(12) -0.0017(12) -0.0010(14) O9 0.0311(16) 0.0302(19) 0.0170(14) -0.0036(13) 0.0025(13) -0.0069(15) O10 0.0157(13) 0.0178(16) 0.0255(15) -0.0001(12) 0.0036(11) -0.0051(12) O11 0.0131(12) 0.0152(15) 0.0263(15) 0.0019(12) -0.0015(11) -0.0006(12) O12 0.0143(13) 0.0136(16) 0.0378(17) -0.0005(13) 0.0023(12) -0.0007(12) O13 0.0398(18) 0.0270(19) 0.0315(18) 0.0053(15) 0.0111(15) 0.0036(17) O14 0.109(5) 0.093(6) 0.172(8) 0.001(5) 0.018(6) -0.018(5) O15 0.122(5) 0.145(6) 0.095(4) 0.065(4) 0.040(4) 0.038(5) O16 0.135(5) 0.271(11) 0.088(5) 0.030(6) -0.039(4) -0.109(7) Sm1 0.01326(9) 0.01049(10) 0.01437(9) 0.00004(7) -0.00034(7) -0.00063(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 O3 1.240(5) . ? C1 O1 1.269(6) . ? C1 C2 1.543(6) . ? C2 O4 1.233(6) . ? C2 O2 1.263(6) . ? C3 O6 1.247(5) . ? C3 O5 1.254(5) . ? C3 C4 1.503(6) . ? C4 C5 1.385(6) . ? C4 C9 1.418(6) . ? C5 C6 1.394(6) . ? C5 H5 0.9500 . ? C6 N1 1.386(5) . ? C6 C7 1.392(7) . ? C7 N2 1.368(6) . ? C7 C8 1.383(6) . ? C8 C9 1.379(6) . ? C8 H8 0.9500 . ? C9 C10 1.486(6) . ? C10 O7 1.259(5) . ? C10 O8 1.259(5) . ? C11 N1 1.309(6) . ? C11 N2 1.336(6) . ? C11 H11 0.9500 . ? C12 O9 1.236(5) . ? C12 O10 1.270(5) . ? C12 C13 1.514(5) . ? C13 C14 1.384(6) . ? C13 C18 1.421(6) . ? C14 C15 1.392(6) . ? C14 H14 0.9500 . ? C15 N4 1.374(6) . ? C15 C16 1.407(7) . ? C16 C17 1.389(6) . ? C16 N3 1.393(5) . ? C17 C18 1.391(6) . ? C17 H17 0.9500 . ? C18 C19 1.487(6) . ? C19 O12 1.257(5) . ? C19 O11 1.279(5) . ? C19 Sm1 2.864(4) 2_655 ? C20 N3 1.310(7) . ? C20 N4 1.339(6) . ? C20 H20 0.9500 . ? Co1 O2 2.097(3) 3_765 ? Co1 O2 2.097(3) . ? Co1 N1 2.115(4) 3_665 ? Co1 N1 2.115(4) 1_655 ? Co1 O1 2.120(3) . ? Co1 O1 2.120(3) 3_765 ? Co2 O5 2.008(3) . ? Co2 O9 2.078(3) . ? Co2 O3 2.096(3) . ? Co2 O4 2.105(3) . ? Co2 N3 2.148(4) 2_745 ? Co2 O13 2.184(4) . ? N1 Co1 2.115(4) 1_455 ? N2 H2 0.8800 . ? N3 Co2 2.148(4) 2_755 ? N4 H4 0.8800 . ? O6 Sm1 2.306(3) . ? O7 Sm1 2.346(3) 1_545 ? O8 Sm1 2.321(3) 2_645 ? O10 Sm1 2.516(3) 2_645 ? O10 Sm1 2.578(3) . ? O11 Sm1 2.400(3) . ? O11 Sm1 2.628(3) 2_655 ? O12 Sm1 2.397(3) 2_655 ? O13 H13A 0.8493 . ? O13 H13B 0.8496 . ? O14 H14A 0.8434 . ? O14 H14B 0.8552 . ? O15 H15A 0.8510 . ? O15 H15B 0.8501 . ? O16 H16A 0.8507 . ? O16 H16B 0.8514 . ? Sm1 O8 2.321(3) 2_655 ? Sm1 O7 2.346(3) 1_565 ? Sm1 O12 2.397(3) 2_645 ? Sm1 O10 2.516(3) 2_655 ? Sm1 O11 2.628(3) 2_645 ? Sm1 C19 2.864(4) 2_645 ? Sm1 Sm1 4.0483(7) 2_655 ? Sm1 Sm1 4.0483(7) 2_645 ? 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 O3 C1 O1 125.3(4) . . ? O3 C1 C2 117.5(4) . . ? O1 C1 C2 117.2(4) . . ? O4 C2 O2 126.1(4) . . ? O4 C2 C1 116.5(4) . . ? O2 C2 C1 117.4(4) . . ? O6 C3 O5 125.9(4) . . ? O6 C3 C4 118.6(4) . . ? O5 C3 C4 115.2(4) . . ? C5 C4 C9 121.7(4) . . ? C5 C4 C3 116.9(4) . . ? C9 C4 C3 121.1(4) . . ? C4 C5 C6 116.5(4) . . ? C4 C5 H5 121.8 . . ? C6 C5 H5 121.8 . . ? N1 C6 C7 108.8(4) . . ? N1 C6 C5 129.8(4) . . ? C7 C6 C5 121.4(4) . . ? N2 C7 C8 132.5(5) . . ? N2 C7 C6 105.2(4) . . ? C8 C7 C6 122.3(4) . . ? C9 C8 C7 116.9(4) . . ? C9 C8 H8 121.6 . . ? C7 C8 H8 121.6 . . ? C8 C9 C4 121.1(4) . . ? C8 C9 C10 119.4(4) . . ? C4 C9 C10 119.3(4) . . ? O7 C10 O8 124.0(4) . . ? O7 C10 C9 117.7(4) . . ? O8 C10 C9 118.3(4) . . ? N1 C11 N2 112.3(4) . . ? N1 C11 H11 123.8 . . ? N2 C11 H11 123.8 . . ? O9 C12 O10 124.8(4) . . ? O9 C12 C13 115.1(4) . . ? O10 C12 C13 120.1(4) . . ? C14 C13 C18 121.2(4) . . ? C14 C13 C12 117.9(4) . . ? C18 C13 C12 120.3(4) . . ? C13 C14 C15 116.7(4) . . ? C13 C14 H14 121.6 . . ? C15 C14 H14 121.6 . . ? N4 C15 C14 132.7(4) . . ? N4 C15 C16 104.4(4) . . ? C14 C15 C16 122.9(4) . . ? C17 C16 N3 131.1(4) . . ? C17 C16 C15 119.8(4) . . ? N3 C16 C15 109.0(4) . . ? C16 C17 C18 118.1(4) . . ? C16 C17 H17 120.9 . . ? C18 C17 H17 120.9 . . ? C17 C18 C13 121.1(4) . . ? C17 C18 C19 117.0(4) . . ? C13 C18 C19 121.8(3) . . ? O12 C19 O11 120.1(4) . . ? O12 C19 C18 120.5(4) . . ? O11 C19 C18 119.3(4) . . ? O12 C19 Sm1 55.9(2) . 2_655 ? O11 C19 Sm1 66.4(2) . 2_655 ? C18 C19 Sm1 160.5(3) . 2_655 ? N3 C20 N4 112.5(4) . . ? N3 C20 H20 123.7 . . ? N4 C20 H20 123.7 . . ? O2 Co1 O2 180.00(17) 3_765 . ? O2 Co1 N1 84.72(14) 3_765 3_665 ? O2 Co1 N1 95.28(14) . 3_665 ? O2 Co1 N1 95.28(14) 3_765 1_655 ? O2 Co1 N1 84.72(14) . 1_655 ? N1 Co1 N1 180.0(2) 3_665 1_655 ? O2 Co1 O1 100.23(13) 3_765 . ? O2 Co1 O1 79.77(13) . . ? N1 Co1 O1 94.68(14) 3_665 . ? N1 Co1 O1 85.32(14) 1_655 . ? O2 Co1 O1 79.77(13) 3_765 3_765 ? O2 Co1 O1 100.23(13) . 3_765 ? N1 Co1 O1 85.32(14) 3_665 3_765 ? N1 Co1 O1 94.68(14) 1_655 3_765 ? O1 Co1 O1 180.00(8) . 3_765 ? O5 Co2 O9 107.54(13) . . ? O5 Co2 O3 162.88(13) . . ? O9 Co2 O3 89.02(13) . . ? O5 Co2 O4 84.29(13) . . ? O9 Co2 O4 166.69(15) . . ? O3 Co2 O4 78.80(13) . . ? O5 Co2 N3 91.14(14) . 2_745 ? O9 Co2 N3 90.79(14) . 2_745 ? O3 Co2 N3 92.99(14) . 2_745 ? O4 Co2 N3 95.16(15) . 2_745 ? O5 Co2 O13 90.04(14) . . ? O9 Co2 O13 85.81(14) . . ? O3 Co2 O13 86.79(14) . . ? O4 Co2 O13 88.13(14) . . ? N3 Co2 O13 176.60(14) 2_745 . ? C11 N1 C6 105.7(4) . . ? C11 N1 Co1 125.9(3) . 1_455 ? C6 N1 Co1 128.2(3) . 1_455 ? C11 N2 C7 108.0(4) . . ? C11 N2 H2 126.0 . . ? C7 N2 H2 126.0 . . ? C20 N3 C16 105.5(4) . . ? C20 N3 Co2 123.3(3) . 2_755 ? C16 N3 Co2 130.4(3) . 2_755 ? C20 N4 C15 108.6(4) . . ? C20 N4 H4 125.7 . . ? C15 N4 H4 125.7 . . ? C1 O1 Co1 108.5(3) . . ? C2 O2 Co1 108.8(3) . . ? C1 O3 Co2 113.2(3) . . ? C2 O4 Co2 113.8(3) . . ? C3 O5 Co2 128.4(3) . . ? C3 O6 Sm1 160.0(3) . . ? C10 O7 Sm1 133.2(3) . 1_545 ? C10 O8 Sm1 135.0(3) . 2_645 ? C12 O9 Co2 140.2(3) . . ? C12 O10 Sm1 149.7(3) . 2_645 ? C12 O10 Sm1 105.0(3) . . ? Sm1 O10 Sm1 105.27(11) 2_645 . ? C19 O11 Sm1 162.9(3) . . ? C19 O11 Sm1 87.1(3) . 2_655 ? Sm1 O11 Sm1 107.15(11) . 2_655 ? C19 O12 Sm1 98.3(2) . 2_655 ? Co2 O13 H13A 117.7 . . ? Co2 O13 H13B 108.9 . . ? H13A O13 H13B 117.2 . . ? H14A O14 H14B 117.1 . . ? H15A O15 H15B 117.0 . . ? H16A O16 H16B 116.9 . . ? O6 Sm1 O8 140.51(11) . 2_655 ? O6 Sm1 O7 69.63(11) . 1_565 ? O8 Sm1 O7 148.23(11) 2_655 1_565 ? O6 Sm1 O12 84.23(11) . 2_645 ? O8 Sm1 O12 94.85(12) 2_655 2_645 ? O7 Sm1 O12 99.20(12) 1_565 2_645 ? O6 Sm1 O11 116.36(11) . . ? O8 Sm1 O11 76.20(11) 2_655 . ? O7 Sm1 O11 79.82(11) 1_565 . ? O12 Sm1 O11 156.81(11) 2_645 . ? O6 Sm1 O10 136.91(10) . 2_655 ? O8 Sm1 O10 81.36(11) 2_655 2_655 ? O7 Sm1 O10 72.72(11) 1_565 2_655 ? O12 Sm1 O10 81.80(10) 2_645 2_655 ? O11 Sm1 O10 75.77(10) . 2_655 ? O6 Sm1 O10 73.79(10) . . ? O8 Sm1 O10 73.52(11) 2_655 . ? O7 Sm1 O10 120.44(11) 1_565 . ? O12 Sm1 O10 122.07(10) 2_645 . ? O11 Sm1 O10 76.42(10) . . ? O10 Sm1 O10 146.12(6) 2_655 . ? O6 Sm1 O11 74.84(11) . 2_645 ? O8 Sm1 O11 74.00(10) 2_655 2_645 ? O7 Sm1 O11 136.10(10) 1_565 2_645 ? O12 Sm1 O11 51.59(10) 2_645 2_645 ? O11 Sm1 O11 140.65(7) . 2_645 ? O10 Sm1 O11 123.50(10) 2_655 2_645 ? O10 Sm1 O11 70.91(9) . 2_645 ? O6 Sm1 C19 74.36(12) . 2_645 ? O8 Sm1 C19 87.87(12) 2_655 2_645 ? O7 Sm1 C19 116.14(12) 1_565 2_645 ? O12 Sm1 C19 25.74(11) 2_645 2_645 ? O11 Sm1 C19 163.78(11) . 2_645 ? O10 Sm1 C19 105.20(11) 2_655 2_645 ? O10 Sm1 C19 96.34(11) . 2_645 ? O11 Sm1 C19 26.48(10) 2_645 2_645 ? O6 Sm1 Sm1 133.83(8) . 2_655 ? O8 Sm1 Sm1 80.32(8) 2_655 2_655 ? O7 Sm1 Sm1 67.96(8) 1_565 2_655 ? O12 Sm1 Sm1 119.68(8) 2_645 2_655 ? O11 Sm1 Sm1 38.34(7) . 2_655 ? O10 Sm1 Sm1 37.90(7) 2_655 2_655 ? O10 Sm1 Sm1 113.91(7) . 2_655 ? O11 Sm1 Sm1 151.29(7) 2_645 2_655 ? C19 Sm1 Sm1 142.36(9) 2_645 2_655 ? O6 Sm1 Sm1 74.81(8) . 2_645 ? O8 Sm1 Sm1 65.76(8) 2_655 2_645 ? O7 Sm1 Sm1 143.22(8) 1_565 2_645 ? O12 Sm1 Sm1 86.10(8) 2_645 2_645 ? O11 Sm1 Sm1 108.69(7) . 2_645 ? O10 Sm1 Sm1 143.78(7) 2_655 2_645 ? O10 Sm1 Sm1 36.83(7) . 2_645 ? O11 Sm1 Sm1 34.51(6) 2_645 2_645 ? C19 Sm1 Sm1 60.76(8) 2_645 2_645 ? Sm1 Sm1 Sm1 139.408(18) 2_655 2_645 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 C1 C2 O4 -3.0(7) . . . . ? O1 C1 C2 O4 177.3(4) . . . . ? O3 C1 C2 O2 176.7(4) . . . . ? O1 C1 C2 O2 -2.9(7) . . . . ? O6 C3 C4 C5 73.6(5) . . . . ? O5 C3 C4 C5 -100.6(5) . . . . ? O6 C3 C4 C9 -113.1(5) . . . . ? O5 C3 C4 C9 72.7(5) . . . . ? C9 C4 C5 C6 1.2(7) . . . . ? C3 C4 C5 C6 174.5(4) . . . . ? C4 C5 C6 N1 -179.6(4) . . . . ? C4 C5 C6 C7 2.4(7) . . . . ? N1 C6 C7 N2 -2.0(5) . . . . ? C5 C6 C7 N2 176.4(4) . . . . ? N1 C6 C7 C8 177.4(4) . . . . ? C5 C6 C7 C8 -4.2(7) . . . . ? N2 C7 C8 C9 -178.5(5) . . . . ? C6 C7 C8 C9 2.2(7) . . . . ? C7 C8 C9 C4 1.3(7) . . . . ? C7 C8 C9 C10 177.0(4) . . . . ? C5 C4 C9 C8 -3.1(7) . . . . ? C3 C4 C9 C8 -176.1(4) . . . . ? C5 C4 C9 C10 -178.8(4) . . . . ? C3 C4 C9 C10 8.2(6) . . . . ? C8 C9 C10 O7 18.2(6) . . . . ? C4 C9 C10 O7 -166.1(4) . . . . ? C8 C9 C10 O8 -162.7(4) . . . . ? C4 C9 C10 O8 13.0(6) . . . . ? O9 C12 C13 C14 -102.0(5) . . . . ? O10 C12 C13 C14 78.0(5) . . . . ? O9 C12 C13 C18 69.4(5) . . . . ? O10 C12 C13 C18 -110.6(5) . . . . ? C18 C13 C14 C15 -3.2(6) . . . . ? C12 C13 C14 C15 168.1(4) . . . . ? C13 C14 C15 N4 -178.0(5) . . . . ? C13 C14 C15 C16 -0.2(7) . . . . ? N4 C15 C16 C17 -178.2(4) . . . . ? C14 C15 C16 C17 3.5(7) . . . . ? N4 C15 C16 N3 1.0(5) . . . . ? C14 C15 C16 N3 -177.3(4) . . . . ? N3 C16 C17 C18 177.9(4) . . . . ? C15 C16 C17 C18 -3.1(6) . . . . ? C16 C17 C18 C13 -0.3(6) . . . . ? C16 C17 C18 C19 175.5(4) . . . . ? C14 C13 C18 C17 3.6(7) . . . . ? C12 C13 C18 C17 -167.5(4) . . . . ? C14 C13 C18 C19 -172.0(4) . . . . ? C12 C13 C18 C19 16.9(6) . . . . ? C17 C18 C19 O12 14.2(6) . . . . ? C13 C18 C19 O12 -170.1(4) . . . . ? C17 C18 C19 O11 -161.4(4) . . . . ? C13 C18 C19 O11 14.4(6) . . . . ? C17 C18 C19 Sm1 -59.2(10) . . . 2_655 ? C13 C18 C19 Sm1 116.6(8) . . . 2_655 ? N2 C11 N1 C6 -1.0(6) . . . . ? N2 C11 N1 Co1 173.8(3) . . . 1_455 ? C7 C6 N1 C11 1.9(5) . . . . ? C5 C6 N1 C11 -176.3(5) . . . . ? C7 C6 N1 Co1 -172.7(3) . . . 1_455 ? C5 C6 N1 Co1 9.0(7) . . . 1_455 ? N1 C11 N2 C7 -0.2(6) . . . . ? C8 C7 N2 C11 -177.9(5) . . . . ? C6 C7 N2 C11 1.4(5) . . . . ? N4 C20 N3 C16 0.0(6) . . . . ? N4 C20 N3 Co2 -171.0(3) . . . 2_755 ? C17 C16 N3 C20 178.5(5) . . . . ? C15 C16 N3 C20 -0.6(5) . . . . ? C17 C16 N3 Co2 -11.4(7) . . . 2_755 ? C15 C16 N3 Co2 169.5(3) . . . 2_755 ? N3 C20 N4 C15 0.7(6) . . . . ? C14 C15 N4 C20 177.1(5) . . . . ? C16 C15 N4 C20 -1.0(6) . . . . ? O3 C1 O1 Co1 161.9(4) . . . . ? C2 C1 O1 Co1 -18.5(5) . . . . ? O2 Co1 O1 C1 -156.7(3) 3_765 . . . ? O2 Co1 O1 C1 23.3(3) . . . . ? N1 Co1 O1 C1 117.8(3) 3_665 . . . ? N1 Co1 O1 C1 -62.2(3) 1_655 . . . ? O4 C2 O2 Co1 -157.4(4) . . . . ? C1 C2 O2 Co1 22.8(5) . . . . ? N1 Co1 O2 C2 -118.7(3) 3_665 . . . ? N1 Co1 O2 C2 61.3(3) 1_655 . . . ? O1 Co1 O2 C2 -24.9(3) . . . . ? O1 Co1 O2 C2 155.1(3) 3_765 . . . ? O1 C1 O3 Co2 -175.9(4) . . . . ? C2 C1 O3 Co2 4.5(5) . . . . ? O5 Co2 O3 C1 -12.5(7) . . . . ? O9 Co2 O3 C1 -178.1(3) . . . . ? O4 Co2 O3 C1 -3.5(3) . . . . ? N3 Co2 O3 C1 91.2(3) 2_745 . . . ? O13 Co2 O3 C1 -92.2(3) . . . . ? O2 C2 O4 Co2 -179.9(4) . . . . ? C1 C2 O4 Co2 -0.1(5) . . . . ? O5 Co2 O4 C2 179.1(4) . . . . ? O9 Co2 O4 C2 26.0(8) . . . . ? O3 Co2 O4 C2 1.8(4) . . . . ? N3 Co2 O4 C2 -90.2(4) 2_745 . . . ? O13 Co2 O4 C2 88.9(4) . . . . ? O6 C3 O5 Co2 -4.8(6) . . . . ? C4 C3 O5 Co2 168.9(3) . . . . ? O9 Co2 O5 C3 38.1(4) . . . . ? O3 Co2 O5 C3 -126.7(5) . . . . ? O4 Co2 O5 C3 -135.7(4) . . . . ? N3 Co2 O5 C3 129.2(4) 2_745 . . . ? O13 Co2 O5 C3 -47.6(4) . . . . ? O5 C3 O6 Sm1 -81.6(10) . . . . ? C4 C3 O6 Sm1 104.8(8) . . . . ? O8 C10 O7 Sm1 40.9(7) . . . 1_545 ? C9 C10 O7 Sm1 -140.0(3) . . . 1_545 ? O7 C10 O8 Sm1 -54.1(7) . . . 2_645 ? C9 C10 O8 Sm1 126.8(4) . . . 2_645 ? O10 C12 O9 Co2 -31.2(7) . . . . ? C13 C12 O9 Co2 148.9(4) . . . . ? O5 Co2 O9 C12 32.5(5) . . . . ? O3 Co2 O9 C12 -151.9(5) . . . . ? O4 Co2 O9 C12 -175.6(5) . . . . ? N3 Co2 O9 C12 -58.9(5) 2_745 . . . ? O13 Co2 O9 C12 121.3(5) . . . . ? O9 C12 O10 Sm1 108.8(6) . . . 2_645 ? C13 C12 O10 Sm1 -71.2(7) . . . 2_645 ? O9 C12 O10 Sm1 -75.1(5) . . . . ? C13 C12 O10 Sm1 104.9(4) . . . . ? O12 C19 O11 Sm1 -163.6(7) . . . . ? C18 C19 O11 Sm1 12.0(12) . . . . ? Sm1 C19 O11 Sm1 -147.2(10) 2_655 . . . ? O12 C19 O11 Sm1 -16.4(4) . . . 2_655 ? C18 C19 O11 Sm1 159.2(4) . . . 2_655 ? O11 C19 O12 Sm1 18.2(4) . . . 2_655 ? C18 C19 O12 Sm1 -157.3(3) . . . 2_655 ? C3 O6 Sm1 O8 -6.8(9) . . . 2_655 ? C3 O6 Sm1 O7 160.5(9) . . . 1_565 ? C3 O6 Sm1 O12 -97.5(9) . . . 2_645 ? C3 O6 Sm1 O11 93.7(9) . . . . ? C3 O6 Sm1 O10 -168.9(8) . . . 2_655 ? C3 O6 Sm1 O10 28.4(8) . . . . ? C3 O6 Sm1 O11 -45.7(8) . . . 2_645 ? C3 O6 Sm1 C19 -73.2(9) . . . 2_645 ? C3 O6 Sm1 Sm1 136.2(8) . . . 2_655 ? C3 O6 Sm1 Sm1 -9.9(8) . . . 2_645 ? C19 O11 Sm1 O6 -86.2(10) . . . . ? Sm1 O11 Sm1 O6 128.28(12) 2_655 . . . ? C19 O11 Sm1 O8 53.7(10) . . . 2_655 ? Sm1 O11 Sm1 O8 -91.80(13) 2_655 . . 2_655 ? C19 O11 Sm1 O7 -147.3(10) . . . 1_565 ? Sm1 O11 Sm1 O7 67.20(12) 2_655 . . 1_565 ? C19 O11 Sm1 O12 123.1(10) . . . 2_645 ? Sm1 O11 Sm1 O12 -22.4(3) 2_655 . . 2_645 ? C19 O11 Sm1 O10 138.2(10) . . . 2_655 ? Sm1 O11 Sm1 O10 -7.38(10) 2_655 . . 2_655 ? C19 O11 Sm1 O10 -22.3(10) . . . . ? Sm1 O11 Sm1 O10 -167.85(13) 2_655 . . . ? C19 O11 Sm1 O11 12.1(10) . . . 2_645 ? Sm1 O11 Sm1 O11 -133.45(15) 2_655 . . 2_645 ? C19 O11 Sm1 C19 42.6(13) . . . 2_645 ? Sm1 O11 Sm1 C19 -102.9(4) 2_655 . . 2_645 ? C19 O11 Sm1 Sm1 145.5(10) . . . 2_655 ? C19 O11 Sm1 Sm1 -4.3(10) . . . 2_645 ? Sm1 O11 Sm1 Sm1 -149.83(7) 2_655 . . 2_645 ? C12 O10 Sm1 O6 95.9(3) . . . . ? Sm1 O10 Sm1 O6 -86.17(12) 2_645 . . . ? C12 O10 Sm1 O8 -106.6(3) . . . 2_655 ? Sm1 O10 Sm1 O8 71.38(12) 2_645 . . 2_655 ? C12 O10 Sm1 O7 42.1(3) . . . 1_565 ? Sm1 O10 Sm1 O7 -139.91(11) 2_645 . . 1_565 ? C12 O10 Sm1 O12 168.1(2) . . . 2_645 ? Sm1 O10 Sm1 O12 -13.97(16) 2_645 . . 2_645 ? C12 O10 Sm1 O11 -27.2(3) . . . . ? Sm1 O10 Sm1 O11 150.75(13) 2_645 . . . ? C12 O10 Sm1 O10 -62.8(2) . . . 2_655 ? Sm1 O10 Sm1 O10 115.18(19) 2_645 . . 2_655 ? C12 O10 Sm1 O11 175.1(3) . . . 2_645 ? Sm1 O10 Sm1 O11 -6.98(10) 2_645 . . 2_645 ? C12 O10 Sm1 C19 167.5(3) . . . 2_645 ? Sm1 O10 Sm1 C19 -14.51(13) 2_645 . . 2_645 ? C12 O10 Sm1 Sm1 -35.4(3) . . . 2_655 ? Sm1 O10 Sm1 Sm1 142.53(7) 2_645 . . 2_655 ? C12 O10 Sm1 Sm1 -178.0(3) . . . 2_645 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O1 0.88 2.00 2.785(6) 147.6 1_445 N2 H2 O14 0.88 2.62 3.105(9) 115.6 1_445 N4 H4 O3 0.88 2.31 3.004(6) 135.6 2_745 N4 H4 O9 0.88 2.52 3.314(6) 149.8 2_745 O13 H13A O16 0.85 2.08 2.832(8) 147.4 . O13 H13B O7 0.85 2.17 2.986(5) 162.0 1_565 O13 H13B O6 0.85 2.47 3.066(5) 127.8 . O15 H15A O14 0.85 2.17 3.017(11) 172.4 4_576 O15 H15B O14 0.85 2.22 2.992(11) 151.7 2_645 O16 H16A O2 0.85 2.18 2.906(9) 142.9 3_665 O16 H16B O15 0.85 2.35 2.935(12) 126.5 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.782 _refine_diff_density_min -2.028 _refine_diff_density_rms 0.214 data_1Pr _database_code_depnum_ccdc_archive 'CCDC 746890' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 Co3 N8 O32 Pr2' _chemical_formula_weight 1595.35 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.477(2) _cell_length_b 7.6575(15) _cell_length_c 30.456(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.06(3) _cell_angle_gamma 90.00 _cell_volume 2413.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 19595 _cell_measurement_theta_min 3.045 _cell_measurement_theta_max 27.51 _exptl_crystal_description sheet _exptl_crystal_colour Purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1566 _exptl_absorpt_coefficient_mu 3.109 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5752 _exptl_absorpt_correction_T_max 0.5752 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22898 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5486 _reflns_number_gt 4998 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0301P)^2^+5.3743P] 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 5486 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0346 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0738 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.002 _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 0.2098(3) 0.5297(4) 0.95545(12) 0.0205(7) Uani 1 1 d . . . C2 C 0.1051(3) 0.4323(4) 0.92292(11) 0.0189(6) Uani 1 1 d . . . C3 C 0.5553(3) 0.6516(4) 0.86153(11) 0.0150(6) Uani 1 1 d . . . C4 C 0.6732(3) 0.7550(4) 0.87945(10) 0.0143(6) Uani 1 1 d . . . C5 C 0.7646(3) 0.6753(4) 0.91047(11) 0.0187(6) Uani 1 1 d . . . H5 H 0.7564 0.5562 0.9183 0.022 Uiso 1 1 calc R . . C6 C 0.8692(3) 0.7750(4) 0.92995(11) 0.0180(6) Uani 1 1 d . . . C7 C 0.8820(3) 0.9492(4) 0.91660(12) 0.0210(7) Uani 1 1 d . . . C8 C 0.7896(3) 1.0315(4) 0.88606(12) 0.0214(7) Uani 1 1 d . . . H8 H 0.7983 1.1502 0.8780 0.026 Uiso 1 1 calc R . . C9 C 0.6841(3) 0.9327(4) 0.86779(10) 0.0165(6) Uani 1 1 d . . . C10 C 0.5841(3) 1.0137(4) 0.83363(11) 0.0185(6) Uani 1 1 d . . . C11 C 1.0476(4) 0.8713(4) 0.96595(13) 0.0250(8) Uani 1 1 d . . . H11 H 1.1274 0.8777 0.9856 0.030 Uiso 1 1 calc R . . C12 C 0.2616(3) 0.5012(4) 0.76694(11) 0.0145(6) Uani 1 1 d . . . C13 C 0.1567(3) 0.4396(4) 0.73044(10) 0.0143(6) Uani 1 1 d . . . C14 C 0.0661(3) 0.5599(4) 0.71142(11) 0.0183(6) Uani 1 1 d . . . H14 H 0.0771 0.6815 0.7169 0.022 Uiso 1 1 calc R . . C15 C -0.0420(3) 0.4947(4) 0.68393(11) 0.0187(6) Uani 1 1 d . . . C16 C -0.0612(3) 0.3155(4) 0.67533(11) 0.0173(6) Uani 1 1 d . . . C17 C 0.0331(3) 0.1961(4) 0.69267(11) 0.0175(6) Uani 1 1 d . . . H17 H 0.0230 0.0751 0.6861 0.021 Uiso 1 1 calc R . . C18 C 0.1423(3) 0.2581(4) 0.71984(10) 0.0148(6) Uani 1 1 d . . . C19 C 0.2473(3) 0.1311(4) 0.73495(11) 0.0146(6) Uani 1 1 d . . . C20 C -0.2293(4) 0.4483(5) 0.64162(13) 0.0281(8) Uani 1 1 d . . . H20 H -0.3112 0.4714 0.6243 0.034 Uiso 1 1 calc R . . Co1 Co 0.0000 0.5000 1.0000 0.01669(13) Uani 1 2 d S . . Co2 Co 0.28646(4) 0.55419(6) 0.869953(14) 0.01627(10) Uani 1 1 d . . . N1 N 0.9739(3) 0.7317(4) 0.96170(10) 0.0204(6) Uani 1 1 d . . . N2 N 0.9993(3) 1.0031(4) 0.93995(11) 0.0267(7) Uani 1 1 d . . . H2 H 1.0356 1.1059 0.9380 0.032 Uiso 1 1 calc R . . N3 N -0.1810(3) 0.2897(4) 0.64863(10) 0.0207(6) Uani 1 1 d . . . N4 N -0.1507(3) 0.5741(4) 0.66149(11) 0.0286(7) Uani 1 1 d . . . H4 H -0.1662 0.6871 0.6603 0.034 Uiso 1 1 calc R . . O1 O 0.0104(2) 0.3702(3) 0.93901(9) 0.0238(5) Uani 1 1 d . . . O2 O 0.1966(2) 0.5356(4) 0.99585(8) 0.0249(5) Uani 1 1 d . . . O3 O 0.1225(2) 0.4197(3) 0.88358(8) 0.0233(5) Uani 1 1 d . . . O4 O 0.3004(2) 0.5948(4) 0.93892(9) 0.0280(6) Uani 1 1 d . . . O5 O 0.4551(2) 0.6865(3) 0.87744(8) 0.0196(5) Uani 1 1 d . . . O6 O 0.5663(2) 0.5290(3) 0.83492(8) 0.0207(5) Uani 1 1 d . . . O7 O 0.5085(2) 0.9143(3) 0.80919(8) 0.0216(5) Uani 1 1 d . . . O8 O 0.5824(3) 1.1780(3) 0.83088(8) 0.0245(5) Uani 1 1 d . . . O9 O 0.2470(2) 0.4604(3) 0.80515(8) 0.0240(5) Uani 1 1 d . . . O10 O 0.3568(2) 0.5893(3) 0.75702(8) 0.0188(5) Uani 1 1 d . . . O11 O 0.3617(2) 0.1856(3) 0.74943(8) 0.0166(4) Uani 1 1 d . . . O12 O 0.2256(2) -0.0306(3) 0.73103(9) 0.0228(5) Uani 1 1 d . . . O13 O 0.3922(3) 0.3102(3) 0.88548(9) 0.0297(6) Uani 1 1 d . . . H13A H 0.4445 0.2841 0.8678 0.045 Uiso 1 1 d R . . H13B H 0.4299 0.3096 0.9122 0.045 Uiso 1 1 d R . . O14 O 0.4901(5) 0.8991(7) 0.95529(16) 0.0924(17) Uani 1 1 d . . . H14A H 0.4760 0.8363 0.9319 0.139 Uiso 1 1 d R . . H14B H 0.5148 0.8309 0.9770 0.139 Uiso 1 1 d R . . O15 O 0.5734(6) 0.2700(11) 0.96516(19) 0.139(3) Uani 1 1 d . . . H15B H 0.6525 0.2739 0.9615 0.208 Uiso 1 1 d R . . H15A H 0.5555 0.3563 0.9809 0.208 Uiso 1 1 d R . . O16 O 0.2730(5) 0.1346(7) 0.9704(2) 0.111(2) Uani 1 1 d . . . H16B H 0.3347 0.0749 0.9848 0.167 Uiso 1 1 d R . . H16A H 0.2899 0.2402 0.9648 0.167 Uiso 1 1 d R . . Pr1 Pr 0.552072(15) 0.37153(2) 0.768208(5) 0.01199(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0187(15) 0.0211(16) 0.0220(17) 0.0005(13) 0.0041(13) -0.0013(13) C2 0.0211(15) 0.0163(15) 0.0201(16) 0.0001(12) 0.0058(13) 0.0001(12) C3 0.0184(15) 0.0112(13) 0.0149(15) 0.0015(11) 0.0009(12) 0.0005(11) C4 0.0148(13) 0.0129(13) 0.0155(14) -0.0017(11) 0.0032(12) -0.0014(11) C5 0.0195(15) 0.0123(14) 0.0241(17) 0.0041(12) 0.0024(13) -0.0010(12) C6 0.0190(15) 0.0150(15) 0.0197(16) 0.0034(12) 0.0024(13) 0.0004(12) C7 0.0213(16) 0.0157(15) 0.0250(18) 0.0012(13) 0.0002(14) -0.0054(13) C8 0.0274(17) 0.0124(14) 0.0234(17) 0.0036(12) 0.0005(14) -0.0028(13) C9 0.0214(15) 0.0136(14) 0.0144(15) 0.0000(11) 0.0023(13) 0.0002(12) C10 0.0264(16) 0.0135(14) 0.0165(16) 0.0004(12) 0.0056(13) 0.0030(13) C11 0.0214(17) 0.0242(17) 0.0265(19) 0.0011(14) -0.0053(15) -0.0054(14) C12 0.0145(14) 0.0105(13) 0.0188(16) -0.0023(11) 0.0036(12) 0.0039(11) C13 0.0143(14) 0.0136(14) 0.0155(15) -0.0023(11) 0.0039(12) -0.0012(11) C14 0.0202(15) 0.0117(14) 0.0226(17) -0.0004(12) 0.0020(13) 0.0013(12) C15 0.0182(15) 0.0139(14) 0.0226(17) 0.0022(12) -0.0006(13) 0.0019(12) C16 0.0154(14) 0.0166(15) 0.0194(16) -0.0002(12) 0.0008(12) 0.0009(12) C17 0.0145(14) 0.0131(14) 0.0248(17) -0.0013(12) 0.0025(13) 0.0009(12) C18 0.0128(13) 0.0142(14) 0.0173(15) 0.0002(11) 0.0017(12) 0.0000(11) C19 0.0125(13) 0.0140(14) 0.0175(16) -0.0005(11) 0.0025(12) 0.0009(11) C20 0.0212(17) 0.0235(17) 0.035(2) 0.0041(15) -0.0102(15) 0.0035(14) Co1 0.0157(3) 0.0190(3) 0.0158(3) 0.0033(2) 0.0036(2) -0.0009(2) Co2 0.0167(2) 0.0169(2) 0.0155(2) -0.00064(16) 0.00313(17) -0.00317(16) N1 0.0175(13) 0.0194(14) 0.0229(15) 0.0029(11) -0.0018(11) -0.0024(11) N2 0.0263(15) 0.0192(14) 0.0313(17) 0.0029(12) -0.0058(13) -0.0112(12) N3 0.0165(13) 0.0185(14) 0.0247(15) 0.0021(11) -0.0039(11) 0.0018(11) N4 0.0253(15) 0.0159(14) 0.0395(19) 0.0021(13) -0.0108(14) 0.0044(12) O1 0.0252(12) 0.0219(12) 0.0257(13) -0.0010(9) 0.0084(11) -0.0073(10) O2 0.0184(11) 0.0395(15) 0.0168(12) 0.0027(10) 0.0031(10) -0.0009(10) O3 0.0254(12) 0.0245(12) 0.0210(13) -0.0031(10) 0.0073(10) -0.0067(10) O4 0.0237(13) 0.0395(15) 0.0222(13) -0.0028(11) 0.0079(11) -0.0107(11) O5 0.0170(11) 0.0197(11) 0.0226(12) -0.0028(9) 0.0042(9) -0.0029(9) O6 0.0267(12) 0.0159(11) 0.0183(12) -0.0054(9) -0.0002(10) 0.0014(9) O7 0.0293(13) 0.0170(11) 0.0161(12) 0.0002(9) -0.0034(10) -0.0010(10) O8 0.0414(14) 0.0113(10) 0.0184(12) 0.0021(9) -0.0031(11) 0.0033(10) O9 0.0300(13) 0.0284(13) 0.0140(12) -0.0037(9) 0.0040(10) -0.0060(11) O10 0.0148(10) 0.0157(11) 0.0253(13) 0.0015(9) 0.0017(9) -0.0033(9) O11 0.0106(10) 0.0136(10) 0.0243(12) -0.0006(9) -0.0010(9) 0.0004(8) O12 0.0137(10) 0.0113(10) 0.0422(15) -0.0022(10) 0.0008(10) 0.0005(8) O13 0.0384(15) 0.0253(13) 0.0275(14) 0.0037(11) 0.0118(12) 0.0047(11) O14 0.114(4) 0.101(4) 0.068(3) -0.041(3) 0.032(3) -0.032(3) O15 0.124(5) 0.204(7) 0.076(4) 0.009(4) -0.025(3) -0.076(5) O16 0.090(4) 0.089(4) 0.147(6) -0.002(4) -0.005(4) -0.009(3) Pr1 0.01238(9) 0.00847(9) 0.01436(10) -0.00002(5) -0.00025(7) -0.00053(5) _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 O4 1.246(4) . ? C1 O2 1.260(4) . ? C1 C2 1.549(5) . ? C2 O3 1.244(4) . ? C2 O1 1.266(4) . ? C3 O5 1.253(4) . ? C3 O6 1.257(4) . ? C3 C4 1.496(4) . ? C4 C5 1.377(5) . ? C4 C9 1.415(4) . ? C5 C6 1.390(5) . ? C5 H5 0.9500 . ? C6 N1 1.383(4) . ? C6 C7 1.407(4) . ? C7 N2 1.382(4) . ? C7 C8 1.384(5) . ? C8 C9 1.382(5) . ? C8 H8 0.9500 . ? C9 C10 1.490(5) . ? C10 O7 1.255(4) . ? C10 O8 1.261(4) . ? C11 N1 1.313(4) . ? C11 N2 1.333(5) . ? C11 H11 0.9500 . ? C12 O9 1.237(4) . ? C12 O10 1.280(4) . ? C12 C13 1.510(4) . ? C13 C14 1.383(4) . ? C13 C18 1.429(4) . ? C14 C15 1.391(5) . ? C14 H14 0.9500 . ? C15 N4 1.375(4) . ? C15 C16 1.405(4) . ? C16 C17 1.388(4) . ? C16 N3 1.398(4) . ? C17 C18 1.387(4) . ? C17 H17 0.9500 . ? C18 C19 1.486(4) . ? C19 O12 1.261(4) . ? C19 O11 1.280(4) . ? C19 Pr1 2.905(3) 2_646 ? C20 N3 1.320(5) . ? C20 N4 1.347(5) . ? C20 H20 0.9500 . ? Co1 O2 2.101(2) 3_567 ? Co1 O2 2.101(2) . ? Co1 N1 2.117(3) 1_455 ? Co1 N1 2.117(3) 3_667 ? Co1 O1 2.124(3) 3_567 ? Co1 O1 2.124(3) . ? Co2 O5 2.018(2) . ? Co2 O9 2.080(2) . ? Co2 O3 2.100(2) . ? Co2 O4 2.106(3) . ? Co2 N3 2.144(3) 2_556 ? Co2 O13 2.186(3) . ? N1 Co1 2.117(3) 1_655 ? N2 H2 0.8800 . ? N3 Co2 2.144(3) 2_546 ? N4 H4 0.8800 . ? O6 Pr1 2.347(2) . ? O7 Pr1 2.366(2) 2_656 ? O8 Pr1 2.398(2) 1_565 ? O10 Pr1 2.530(2) 2_656 ? O10 Pr1 2.619(2) . ? O11 Pr1 2.444(2) . ? O11 Pr1 2.653(2) 2_646 ? O12 Pr1 2.444(2) 2_646 ? O13 H13A 0.8496 . ? O13 H13B 0.8464 . ? O14 H14A 0.8542 . ? O14 H14B 0.8501 . ? O15 H15B 0.8544 . ? O15 H15A 0.8542 . ? O16 H16B 0.8537 . ? O16 H16A 0.8506 . ? Pr1 O7 2.366(2) 2_646 ? Pr1 O8 2.398(2) 1_545 ? Pr1 O12 2.444(2) 2_656 ? Pr1 O10 2.530(2) 2_646 ? Pr1 O11 2.653(2) 2_656 ? Pr1 C19 2.905(3) 2_656 ? Pr1 Pr1 4.0864(7) 2_646 ? Pr1 Pr1 4.0864(7) 2_656 ? 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 O4 C1 O2 126.0(3) . . ? O4 C1 C2 116.2(3) . . ? O2 C1 C2 117.8(3) . . ? O3 C2 O1 125.9(3) . . ? O3 C2 C1 117.2(3) . . ? O1 C2 C1 116.9(3) . . ? O5 C3 O6 125.1(3) . . ? O5 C3 C4 116.1(3) . . ? O6 C3 C4 118.5(3) . . ? C5 C4 C9 121.6(3) . . ? C5 C4 C3 117.4(3) . . ? C9 C4 C3 120.8(3) . . ? C4 C5 C6 117.7(3) . . ? C4 C5 H5 121.1 . . ? C6 C5 H5 121.1 . . ? N1 C6 C5 130.7(3) . . ? N1 C6 C7 109.1(3) . . ? C5 C6 C7 120.1(3) . . ? N2 C7 C8 132.9(3) . . ? N2 C7 C6 104.6(3) . . ? C8 C7 C6 122.5(3) . . ? C9 C8 C7 116.9(3) . . ? C9 C8 H8 121.5 . . ? C7 C8 H8 121.5 . . ? C8 C9 C4 121.0(3) . . ? C8 C9 C10 118.9(3) . . ? C4 C9 C10 120.0(3) . . ? O7 C10 O8 124.4(3) . . ? O7 C10 C9 118.0(3) . . ? O8 C10 C9 117.6(3) . . ? N1 C11 N2 113.3(3) . . ? N1 C11 H11 123.3 . . ? N2 C11 H11 123.3 . . ? O9 C12 O10 124.9(3) . . ? O9 C12 C13 115.5(3) . . ? O10 C12 C13 119.7(3) . . ? C14 C13 C18 120.8(3) . . ? C14 C13 C12 118.2(3) . . ? C18 C13 C12 120.6(3) . . ? C13 C14 C15 117.0(3) . . ? C13 C14 H14 121.5 . . ? C15 C14 H14 121.5 . . ? N4 C15 C14 132.3(3) . . ? N4 C15 C16 104.8(3) . . ? C14 C15 C16 122.8(3) . . ? C17 C16 N3 130.4(3) . . ? C17 C16 C15 120.0(3) . . ? N3 C16 C15 109.6(3) . . ? C18 C17 C16 118.2(3) . . ? C18 C17 H17 120.9 . . ? C16 C17 H17 120.9 . . ? C17 C18 C13 121.0(3) . . ? C17 C18 C19 117.5(3) . . ? C13 C18 C19 121.3(3) . . ? O12 C19 O11 119.9(3) . . ? O12 C19 C18 120.0(3) . . ? O11 C19 C18 120.0(3) . . ? O12 C19 Pr1 56.36(15) . 2_646 ? O11 C19 Pr1 65.88(16) . 2_646 ? C18 C19 Pr1 160.3(2) . 2_646 ? N3 C20 N4 113.2(3) . . ? N3 C20 H20 123.4 . . ? N4 C20 H20 123.4 . . ? O2 Co1 O2 180.000(2) 3_567 . ? O2 Co1 N1 95.69(10) 3_567 1_455 ? O2 Co1 N1 84.31(10) . 1_455 ? O2 Co1 N1 84.31(10) 3_567 3_667 ? O2 Co1 N1 95.69(10) . 3_667 ? N1 Co1 N1 180.000(1) 1_455 3_667 ? O2 Co1 O1 79.77(10) 3_567 3_567 ? O2 Co1 O1 100.23(10) . 3_567 ? N1 Co1 O1 94.00(11) 1_455 3_567 ? N1 Co1 O1 86.00(11) 3_667 3_567 ? O2 Co1 O1 100.23(10) 3_567 . ? O2 Co1 O1 79.77(10) . . ? N1 Co1 O1 86.00(11) 1_455 . ? N1 Co1 O1 94.00(11) 3_667 . ? O1 Co1 O1 180.000(1) 3_567 . ? O5 Co2 O9 108.69(10) . . ? O5 Co2 O3 162.33(10) . . ? O9 Co2 O3 88.37(10) . . ? O5 Co2 O4 83.74(10) . . ? O9 Co2 O4 165.92(10) . . ? O3 Co2 O4 78.80(10) . . ? O5 Co2 N3 90.75(10) . 2_556 ? O9 Co2 N3 91.31(11) . 2_556 ? O3 Co2 N3 93.51(11) . 2_556 ? O4 Co2 N3 95.22(11) . 2_556 ? O5 Co2 O13 89.98(10) . . ? O9 Co2 O13 85.89(10) . . ? O3 Co2 O13 86.60(10) . . ? O4 Co2 O13 87.55(11) . . ? N3 Co2 O13 177.20(11) 2_556 . ? C11 N1 C6 105.2(3) . . ? C11 N1 Co1 127.2(2) . 1_655 ? C6 N1 Co1 127.3(2) . 1_655 ? C11 N2 C7 107.6(3) . . ? C11 N2 H2 126.2 . . ? C7 N2 H2 126.2 . . ? C20 N3 C16 104.5(3) . . ? C20 N3 Co2 124.2(2) . 2_546 ? C16 N3 Co2 130.6(2) . 2_546 ? C20 N4 C15 107.9(3) . . ? C20 N4 H4 126.1 . . ? C15 N4 H4 126.1 . . ? C2 O1 Co1 108.3(2) . . ? C1 O2 Co1 108.3(2) . . ? C2 O3 Co2 113.6(2) . . ? C1 O4 Co2 114.0(2) . . ? C3 O5 Co2 128.4(2) . . ? C3 O6 Pr1 160.4(2) . . ? C10 O7 Pr1 136.1(2) . 2_656 ? C10 O8 Pr1 131.9(2) . 1_565 ? C12 O9 Co2 140.3(2) . . ? C12 O10 Pr1 150.15(19) . 2_656 ? C12 O10 Pr1 104.83(18) . . ? Pr1 O10 Pr1 105.01(8) 2_656 . ? C19 O11 Pr1 162.9(2) . . ? C19 O11 Pr1 87.99(17) . 2_646 ? Pr1 O11 Pr1 106.51(7) . 2_646 ? C19 O12 Pr1 98.21(18) . 2_646 ? Co2 O13 H13A 114.8 . . ? Co2 O13 H13B 110.9 . . ? H13A O13 H13B 111.0 . . ? H14A O14 H14B 107.1 . . ? H15B O15 H15A 110.4 . . ? H16B O16 H16A 116.5 . . ? O6 Pr1 O7 139.64(8) . 2_646 ? O6 Pr1 O8 69.27(8) . 1_545 ? O7 Pr1 O8 149.31(8) 2_646 1_545 ? O6 Pr1 O12 84.48(9) . 2_656 ? O7 Pr1 O12 94.19(9) 2_646 2_656 ? O8 Pr1 O12 100.11(9) 1_545 2_656 ? O6 Pr1 O11 116.11(8) . . ? O7 Pr1 O11 76.48(8) 2_646 . ? O8 Pr1 O11 80.05(9) 1_545 . ? O12 Pr1 O11 157.29(8) 2_656 . ? O6 Pr1 O10 136.57(8) . 2_646 ? O7 Pr1 O10 82.56(8) 2_646 2_646 ? O8 Pr1 O10 72.84(8) 1_545 2_646 ? O12 Pr1 O10 81.97(8) 2_656 2_646 ? O11 Pr1 O10 76.36(7) . 2_646 ? O6 Pr1 O10 74.17(8) . . ? O7 Pr1 O10 72.58(8) 2_646 . ? O8 Pr1 O10 119.98(8) 1_545 . ? O12 Pr1 O10 121.98(7) 2_656 . ? O11 Pr1 O10 75.44(7) . . ? O10 Pr1 O10 145.93(4) 2_646 . ? O6 Pr1 O11 74.48(8) . 2_656 ? O7 Pr1 O11 73.71(8) 2_646 2_656 ? O8 Pr1 O11 135.61(8) 1_545 2_656 ? O12 Pr1 O11 50.92(7) 2_656 2_656 ? O11 Pr1 O11 140.53(5) . 2_656 ? O10 Pr1 O11 123.78(7) 2_646 2_656 ? O10 Pr1 O11 71.36(7) . 2_656 ? O6 Pr1 C19 74.31(9) . 2_656 ? O7 Pr1 C19 87.39(9) 2_646 2_656 ? O8 Pr1 C19 116.31(9) 1_545 2_656 ? O12 Pr1 C19 25.44(8) 2_656 2_656 ? O11 Pr1 C19 163.49(8) . 2_656 ? O10 Pr1 C19 105.35(8) 2_646 2_656 ? O10 Pr1 C19 96.57(8) . 2_656 ? O11 Pr1 C19 26.13(8) 2_656 2_656 ? O6 Pr1 Pr1 133.96(6) . 2_646 ? O7 Pr1 Pr1 80.84(6) 2_646 2_646 ? O8 Pr1 Pr1 68.48(6) 1_545 2_646 ? O12 Pr1 Pr1 120.22(6) 2_656 2_646 ? O11 Pr1 Pr1 38.50(5) . 2_646 ? O10 Pr1 Pr1 38.25(5) 2_646 2_646 ? O10 Pr1 Pr1 113.05(5) . 2_646 ? O11 Pr1 Pr1 151.54(5) 2_656 2_646 ? C19 Pr1 Pr1 142.71(6) 2_656 2_646 ? O6 Pr1 Pr1 74.42(6) . 2_656 ? O7 Pr1 Pr1 65.26(6) 2_646 2_656 ? O8 Pr1 Pr1 142.31(6) 1_545 2_656 ? O12 Pr1 Pr1 85.90(5) 2_656 2_656 ? O11 Pr1 Pr1 108.01(5) . 2_656 ? O10 Pr1 Pr1 144.60(6) 2_646 2_656 ? O10 Pr1 Pr1 36.73(5) . 2_656 ? O11 Pr1 Pr1 34.99(5) 2_656 2_656 ? C19 Pr1 Pr1 60.91(6) 2_656 2_656 ? Pr1 Pr1 Pr1 139.088(17) 2_646 2_656 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C1 C2 O3 3.3(5) . . . . ? O2 C1 C2 O3 -176.5(3) . . . . ? O4 C1 C2 O1 -177.8(3) . . . . ? O2 C1 C2 O1 2.4(5) . . . . ? O5 C3 C4 C5 101.7(3) . . . . ? O6 C3 C4 C5 -72.7(4) . . . . ? O5 C3 C4 C9 -72.8(4) . . . . ? O6 C3 C4 C9 112.8(3) . . . . ? C9 C4 C5 C6 -0.5(5) . . . . ? C3 C4 C5 C6 -174.9(3) . . . . ? C4 C5 C6 N1 179.7(3) . . . . ? C4 C5 C6 C7 -2.5(5) . . . . ? N1 C6 C7 N2 2.5(4) . . . . ? C5 C6 C7 N2 -175.7(3) . . . . ? N1 C6 C7 C8 -177.9(3) . . . . ? C5 C6 C7 C8 3.8(5) . . . . ? N2 C7 C8 C9 177.5(4) . . . . ? C6 C7 C8 C9 -1.9(5) . . . . ? C7 C8 C9 C4 -1.1(5) . . . . ? C7 C8 C9 C10 -178.0(3) . . . . ? C5 C4 C9 C8 2.3(5) . . . . ? C3 C4 C9 C8 176.5(3) . . . . ? C5 C4 C9 C10 179.2(3) . . . . ? C3 C4 C9 C10 -6.6(4) . . . . ? C8 C9 C10 O7 161.7(3) . . . . ? C4 C9 C10 O7 -15.3(5) . . . . ? C8 C9 C10 O8 -17.4(5) . . . . ? C4 C9 C10 O8 165.7(3) . . . . ? O9 C12 C13 C14 103.2(3) . . . . ? O10 C12 C13 C14 -76.9(4) . . . . ? O9 C12 C13 C18 -69.2(4) . . . . ? O10 C12 C13 C18 110.8(3) . . . . ? C18 C13 C14 C15 3.7(5) . . . . ? C12 C13 C14 C15 -168.6(3) . . . . ? C13 C14 C15 N4 177.2(4) . . . . ? C13 C14 C15 C16 0.2(5) . . . . ? N4 C15 C16 C17 178.8(3) . . . . ? C14 C15 C16 C17 -3.5(5) . . . . ? N4 C15 C16 N3 -0.9(4) . . . . ? C14 C15 C16 N3 176.8(3) . . . . ? N3 C16 C17 C18 -177.7(3) . . . . ? C15 C16 C17 C18 2.7(5) . . . . ? C16 C17 C18 C13 1.1(5) . . . . ? C16 C17 C18 C19 -174.8(3) . . . . ? C14 C13 C18 C17 -4.5(5) . . . . ? C12 C13 C18 C17 167.6(3) . . . . ? C14 C13 C18 C19 171.4(3) . . . . ? C12 C13 C18 C19 -16.5(4) . . . . ? C17 C18 C19 O12 -14.7(5) . . . . ? C13 C18 C19 O12 169.4(3) . . . . ? C17 C18 C19 O11 161.1(3) . . . . ? C13 C18 C19 O11 -14.9(5) . . . . ? C17 C18 C19 Pr1 58.6(7) . . . 2_646 ? C13 C18 C19 Pr1 -117.3(6) . . . 2_646 ? N2 C11 N1 C6 0.6(4) . . . . ? N2 C11 N1 Co1 -173.6(3) . . . 1_655 ? C5 C6 N1 C11 176.1(4) . . . . ? C7 C6 N1 C11 -2.0(4) . . . . ? C5 C6 N1 Co1 -9.7(5) . . . 1_655 ? C7 C6 N1 Co1 172.3(2) . . . 1_655 ? N1 C11 N2 C7 1.0(5) . . . . ? C8 C7 N2 C11 178.4(4) . . . . ? C6 C7 N2 C11 -2.1(4) . . . . ? N4 C20 N3 C16 0.1(4) . . . . ? N4 C20 N3 Co2 171.5(3) . . . 2_546 ? C17 C16 N3 C20 -179.1(4) . . . . ? C15 C16 N3 C20 0.5(4) . . . . ? C17 C16 N3 Co2 10.2(5) . . . 2_546 ? C15 C16 N3 Co2 -170.2(2) . . . 2_546 ? N3 C20 N4 C15 -0.6(5) . . . . ? C14 C15 N4 C20 -176.5(4) . . . . ? C16 C15 N4 C20 0.9(4) . . . . ? O3 C2 O1 Co1 -161.7(3) . . . . ? C1 C2 O1 Co1 19.6(3) . . . . ? O2 Co1 O1 C2 155.7(2) 3_567 . . . ? O2 Co1 O1 C2 -24.3(2) . . . . ? N1 Co1 O1 C2 60.6(2) 1_455 . . . ? N1 Co1 O1 C2 -119.4(2) 3_667 . . . ? O4 C1 O2 Co1 157.1(3) . . . . ? C2 C1 O2 Co1 -23.1(4) . . . . ? N1 Co1 O2 C1 -61.4(2) 1_455 . . . ? N1 Co1 O2 C1 118.6(2) 3_667 . . . ? O1 Co1 O2 C1 -154.5(2) 3_567 . . . ? O1 Co1 O2 C1 25.5(2) . . . . ? O1 C2 O3 Co2 176.6(3) . . . . ? C1 C2 O3 Co2 -4.7(4) . . . . ? O5 Co2 O3 C2 12.6(5) . . . . ? O9 Co2 O3 C2 177.7(2) . . . . ? O4 Co2 O3 C2 3.6(2) . . . . ? N3 Co2 O3 C2 -91.0(2) 2_556 . . . ? O13 Co2 O3 C2 91.8(2) . . . . ? O2 C1 O4 Co2 179.7(3) . . . . ? C2 C1 O4 Co2 0.0(4) . . . . ? O5 Co2 O4 C1 -179.0(3) . . . . ? O9 Co2 O4 C1 -26.4(6) . . . . ? O3 Co2 O4 C1 -1.7(2) . . . . ? N3 Co2 O4 C1 90.8(3) 2_556 . . . ? O13 Co2 O4 C1 -88.7(3) . . . . ? O6 C3 O5 Co2 4.7(5) . . . . ? C4 C3 O5 Co2 -169.3(2) . . . . ? O9 Co2 O5 C3 -37.8(3) . . . . ? O3 Co2 O5 C3 126.5(3) . . . . ? O4 Co2 O5 C3 135.4(3) . . . . ? N3 Co2 O5 C3 -129.5(3) 2_556 . . . ? O13 Co2 O5 C3 47.8(3) . . . . ? O5 C3 O6 Pr1 81.5(7) . . . . ? C4 C3 O6 Pr1 -104.7(6) . . . . ? O8 C10 O7 Pr1 54.3(5) . . . 2_656 ? C9 C10 O7 Pr1 -124.7(3) . . . 2_656 ? O7 C10 O8 Pr1 -40.5(5) . . . 1_565 ? C9 C10 O8 Pr1 138.5(3) . . . 1_565 ? O10 C12 O9 Co2 32.1(5) . . . . ? C13 C12 O9 Co2 -147.9(3) . . . . ? O5 Co2 O9 C12 -33.8(4) . . . . ? O3 Co2 O9 C12 150.9(4) . . . . ? O4 Co2 O9 C12 175.1(4) . . . . ? N3 Co2 O9 C12 57.4(4) 2_556 . . . ? O13 Co2 O9 C12 -122.4(4) . . . . ? O9 C12 O10 Pr1 -106.2(4) . . . 2_656 ? C13 C12 O10 Pr1 73.8(5) . . . 2_656 ? O9 C12 O10 Pr1 73.9(3) . . . . ? C13 C12 O10 Pr1 -106.1(2) . . . . ? O12 C19 O11 Pr1 165.5(5) . . . . ? C18 C19 O11 Pr1 -10.3(9) . . . . ? Pr1 C19 O11 Pr1 148.6(7) 2_646 . . . ? O12 C19 O11 Pr1 16.9(3) . . . 2_646 ? C18 C19 O11 Pr1 -158.9(3) . . . 2_646 ? O11 C19 O12 Pr1 -18.6(3) . . . 2_646 ? C18 C19 O12 Pr1 157.2(3) . . . 2_646 ? C3 O6 Pr1 O7 6.7(7) . . . 2_646 ? C3 O6 Pr1 O8 -160.3(7) . . . 1_545 ? C3 O6 Pr1 O12 96.7(7) . . . 2_656 ? C3 O6 Pr1 O11 -93.4(7) . . . . ? C3 O6 Pr1 O10 168.8(6) . . . 2_646 ? C3 O6 Pr1 O10 -28.8(7) . . . . ? C3 O6 Pr1 O11 45.8(7) . . . 2_656 ? C3 O6 Pr1 C19 72.9(7) . . . 2_656 ? C3 O6 Pr1 Pr1 -135.8(6) . . . 2_646 ? C3 O6 Pr1 Pr1 9.4(6) . . . 2_656 ? C19 O11 Pr1 O6 84.2(7) . . . . ? Pr1 O11 Pr1 O6 -128.73(9) 2_646 . . . ? C19 O11 Pr1 O7 -54.8(7) . . . 2_646 ? Pr1 O11 Pr1 O7 92.26(9) 2_646 . . 2_646 ? C19 O11 Pr1 O8 145.1(7) . . . 1_545 ? Pr1 O11 Pr1 O8 -67.82(9) 2_646 . . 1_545 ? C19 O11 Pr1 O12 -122.5(7) . . . 2_656 ? Pr1 O11 Pr1 O12 24.6(2) 2_646 . . 2_656 ? C19 O11 Pr1 O10 -140.3(7) . . . 2_646 ? Pr1 O11 Pr1 O10 6.77(8) 2_646 . . 2_646 ? C19 O11 Pr1 O10 20.4(7) . . . . ? Pr1 O11 Pr1 O10 167.44(10) 2_646 . . . ? C19 O11 Pr1 O11 -13.1(7) . . . 2_656 ? Pr1 O11 Pr1 O11 134.02(10) 2_646 . . 2_656 ? C19 O11 Pr1 C19 -42.3(9) . . . 2_656 ? Pr1 O11 Pr1 C19 104.8(3) 2_646 . . 2_656 ? C19 O11 Pr1 Pr1 -147.1(8) . . . 2_646 ? C19 O11 Pr1 Pr1 3.1(7) . . . 2_656 ? Pr1 O11 Pr1 Pr1 150.20(5) 2_646 . . 2_656 ? C12 O10 Pr1 O6 -95.0(2) . . . . ? Pr1 O10 Pr1 O6 85.01(10) 2_656 . . . ? C12 O10 Pr1 O7 108.2(2) . . . 2_646 ? Pr1 O10 Pr1 O7 -71.77(9) 2_656 . . 2_646 ? C12 O10 Pr1 O8 -41.1(2) . . . 1_545 ? Pr1 O10 Pr1 O8 138.97(9) 2_656 . . 1_545 ? C12 O10 Pr1 O12 -167.89(19) . . . 2_656 ? Pr1 O10 Pr1 O12 12.16(13) 2_656 . . 2_656 ? C12 O10 Pr1 O11 28.07(19) . . . . ? Pr1 O10 Pr1 O11 -151.88(10) 2_656 . . . ? C12 O10 Pr1 O10 63.11(19) . . . 2_646 ? Pr1 O10 Pr1 O10 -116.84(13) 2_656 . . 2_646 ? C12 O10 Pr1 O11 -173.6(2) . . . 2_656 ? Pr1 O10 Pr1 O11 6.43(7) 2_656 . . 2_656 ? C12 O10 Pr1 C19 -166.6(2) . . . 2_656 ? Pr1 O10 Pr1 C19 13.41(10) 2_656 . . 2_656 ? C12 O10 Pr1 Pr1 36.5(2) . . . 2_646 ? Pr1 O10 Pr1 Pr1 -143.42(5) 2_656 . . 2_646 ? C12 O10 Pr1 Pr1 180.0(2) . . . 2_656 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O16 H16B O14 0.85 2.39 2.995(8) 127.9 1_545 O16 H16B O14 0.85 2.38 3.095(8) 141.0 3_667 O15 H15B O2 0.85 2.38 2.922(6) 121.7 3_667 O14 H14B O16 0.85 2.54 3.095(8) 123.7 3_667 O14 H14B O15 0.85 2.25 2.915(8) 135.0 3_667 O14 H14A O4 0.85 2.64 3.052(5) 110.9 . O14 H14A O5 0.85 2.00 2.852(5) 176.4 . O13 H13B O15 0.85 2.05 2.852(6) 158.7 . O13 H13A O6 0.85 2.56 3.064(4) 119.0 . O13 H13A O8 0.85 2.13 2.967(4) 169.7 1_545 N4 H4 O9 0.88 2.55 3.335(4) 149.6 2_556 N4 H4 O3 0.88 2.32 3.017(4) 136.7 2_556 N2 H2 O16 0.88 2.54 3.043(6) 117.3 1_665 N2 H2 O1 0.88 2.04 2.814(4) 145.8 1_665 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.027 _refine_diff_density_min -1.559 _refine_diff_density_rms 0.133 data_2Nd _database_code_depnum_ccdc_archive 'CCDC 746891' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H32 Co3 N8 Nd2 O32' _chemical_formula_weight 1602.01 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' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Nd Nd -0.1943 3.0179 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 10.467(2) _cell_length_b 7.6374(15) _cell_length_c 30.492(6) _cell_angle_alpha 90.00 _cell_angle_beta 99.05(3) _cell_angle_gamma 90.00 _cell_volume 2407.3(8) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 20070 _cell_measurement_theta_min 3.085 _cell_measurement_theta_max 27.505 _exptl_crystal_description sheet _exptl_crystal_colour Purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1570 _exptl_absorpt_coefficient_mu 3.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5627 _exptl_absorpt_correction_T_max 0.5627 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22900 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0574 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5499 _reflns_number_gt 5061 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0240P)^2^+3.6708P] 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 5499 _refine_ls_number_parameters 385 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0319 _refine_ls_R_factor_gt 0.0285 _refine_ls_wR_factor_ref 0.0707 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.2099(3) 0.0296(4) 0.95539(10) 0.0188(6) Uani 1 1 d . . . C2 C 0.1049(3) -0.0677(4) 0.92279(10) 0.0188(6) Uani 1 1 d . . . C3 C 0.5553(3) 0.1507(3) 0.86095(9) 0.0151(5) Uani 1 1 d . . . C4 C 0.6730(3) 0.2552(3) 0.87909(9) 0.0144(5) Uani 1 1 d . . . C5 C 0.7647(3) 0.1745(4) 0.91042(10) 0.0189(6) Uani 1 1 d . . . H5 H 0.7565 0.0552 0.9183 0.023 Uiso 1 1 calc R . . C6 C 0.8687(3) 0.2751(4) 0.92973(10) 0.0178(5) Uani 1 1 d . . . C7 C 0.8822(3) 0.4495(4) 0.91647(10) 0.0206(6) Uani 1 1 d . . . C8 C 0.7905(3) 0.5319(4) 0.88586(10) 0.0218(6) Uani 1 1 d . . . H8 H 0.7997 0.6509 0.8778 0.026 Uiso 1 1 calc R . . C9 C 0.6845(3) 0.4332(4) 0.86744(9) 0.0169(5) Uani 1 1 d . . . C10 C 0.5849(3) 0.5135(4) 0.83320(9) 0.0174(5) Uani 1 1 d . . . C11 C 1.0475(3) 0.3716(4) 0.96610(12) 0.0245(7) Uani 1 1 d . . . H11 H 1.1272 0.3781 0.9858 0.029 Uiso 1 1 calc R . . C12 C 0.2622(3) 0.0017(3) 0.76696(10) 0.0143(5) Uani 1 1 d . . . C13 C 0.1579(2) -0.0601(3) 0.73042(9) 0.0137(5) Uani 1 1 d . . . C14 C 0.0668(3) 0.0604(3) 0.71152(10) 0.0181(6) Uani 1 1 d . . . H14 H 0.0777 0.1823 0.7170 0.022 Uiso 1 1 calc R . . C15 C -0.0414(3) -0.0052(4) 0.68412(10) 0.0186(6) Uani 1 1 d . . . C16 C -0.0606(3) -0.1852(4) 0.67557(10) 0.0174(5) Uani 1 1 d . . . C17 C 0.0346(3) -0.3042(3) 0.69280(10) 0.0163(5) Uani 1 1 d . . . H17 H 0.0251 -0.4254 0.6861 0.020 Uiso 1 1 calc R . . C18 C 0.1432(2) -0.2419(3) 0.71984(9) 0.0148(5) Uani 1 1 d . . . C19 C 0.2486(3) -0.3687(3) 0.73488(10) 0.0157(6) Uani 1 1 d . . . C20 C -0.2286(3) -0.0521(4) 0.64154(12) 0.0288(7) Uani 1 1 d . . . H20 H -0.3105 -0.0294 0.6242 0.035 Uiso 1 1 calc R . . Co1 Co 0.0000 0.0000 1.0000 0.01639(12) Uani 1 2 d S . . Co2 Co 0.28631(4) 0.05381(5) 0.869886(13) 0.01614(9) Uani 1 1 d . . . N1 N 0.9731(2) 0.2314(3) 0.96174(9) 0.0200(5) Uani 1 1 d . . . N2 N 0.9989(3) 0.5039(3) 0.93977(10) 0.0264(6) Uani 1 1 d . . . H2 H 1.0351 0.6070 0.9377 0.032 Uiso 1 1 calc R . . N3 N -0.1799(2) -0.2103(3) 0.64869(9) 0.0219(5) Uani 1 1 d . . . N4 N -0.1500(3) 0.0748(3) 0.66144(10) 0.0271(6) Uani 1 1 d . . . H4 H -0.1654 0.1881 0.6601 0.033 Uiso 1 1 calc R . . Nd1 Nd 0.551791(13) -0.128182(17) 0.768103(5) 0.01191(6) Uani 1 1 d . . . O1 O 0.0097(2) -0.1285(3) 0.93881(8) 0.0226(5) Uani 1 1 d . . . O2 O 0.1969(2) 0.0358(3) 0.99567(7) 0.0240(5) Uani 1 1 d . . . O3 O 0.1222(2) -0.0803(3) 0.88354(7) 0.0225(4) Uani 1 1 d . . . O4 O 0.3004(2) 0.0946(3) 0.93879(8) 0.0274(5) Uani 1 1 d . . . O5 O 0.45508(19) 0.1862(3) 0.87716(7) 0.0192(4) Uani 1 1 d . . . O6 O 0.5656(2) 0.0292(3) 0.83447(7) 0.0210(4) Uani 1 1 d . . . O7 O 0.5087(2) 0.4138(3) 0.80887(7) 0.0218(4) Uani 1 1 d . . . O8 O 0.5830(2) 0.6789(3) 0.83023(7) 0.0243(5) Uani 1 1 d . . . O9 O 0.2474(2) -0.0393(3) 0.80509(7) 0.0243(5) Uani 1 1 d . . . O10 O 0.35833(18) 0.0899(3) 0.75723(7) 0.0180(4) Uani 1 1 d . . . O11 O 0.36292(18) -0.3146(2) 0.74952(7) 0.0174(4) Uani 1 1 d . . . O12 O 0.22682(19) -0.5313(3) 0.73093(8) 0.0225(5) Uani 1 1 d . . . O13 O 0.3927(2) -0.1906(3) 0.88531(8) 0.0299(5) Uani 1 1 d . . . H13A H 0.4355 -0.1966 0.9112 0.045 Uiso 1 1 d R . . H13B H 0.4443 -0.2161 0.8674 0.045 Uiso 1 1 d R . . O14 O 0.4883(4) 0.4000(5) 0.95461(14) 0.0828(13) Uani 1 1 d . . . H14A H 0.4852 0.3146 0.9365 0.124 Uiso 1 1 d R . . H14B H 0.5536 0.3764 0.9742 0.124 Uiso 1 1 d R . . O15 O 0.5749(5) 0.7654(8) 0.96524(16) 0.1174(19) Uani 1 1 d . . . H15B H 0.5516 0.8686 0.9710 0.176 Uiso 1 1 d R . . H15A H 0.6540 0.7650 0.9617 0.176 Uiso 1 1 d R . . O16 O 0.2722(4) 0.6359(5) 0.97020(17) 0.0907(15) Uani 1 1 d . . . H16A H 0.3359 0.5660 0.9699 0.136 Uiso 1 1 d R . . H16B H 0.2924 0.7387 0.9796 0.136 Uiso 1 1 d 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 C1 0.0164(14) 0.0214(14) 0.0187(14) 0.0003(12) 0.0027(11) 0.0011(10) C2 0.0199(14) 0.0148(13) 0.0218(15) 0.0014(12) 0.0036(11) 0.0006(10) C3 0.0182(13) 0.0131(12) 0.0128(13) 0.0030(11) -0.0010(10) 0.0007(9) C4 0.0156(13) 0.0130(12) 0.0143(13) -0.0018(11) 0.0013(10) 0.0000(9) C5 0.0193(14) 0.0142(12) 0.0231(15) 0.0040(12) 0.0025(11) -0.0015(10) C6 0.0178(13) 0.0159(13) 0.0191(14) 0.0029(11) 0.0013(11) 0.0000(10) C7 0.0229(15) 0.0157(13) 0.0223(15) -0.0007(12) 0.0014(12) -0.0043(10) C8 0.0267(15) 0.0135(13) 0.0239(16) 0.0029(12) -0.0002(12) -0.0031(11) C9 0.0213(14) 0.0144(12) 0.0147(13) 0.0006(11) 0.0020(11) 0.0000(10) C10 0.0248(15) 0.0142(12) 0.0129(13) 0.0002(11) 0.0016(11) 0.0026(10) C11 0.0209(15) 0.0247(16) 0.0261(17) 0.0018(13) -0.0021(13) -0.0034(11) C12 0.0136(12) 0.0105(11) 0.0191(14) -0.0026(11) 0.0030(10) 0.0029(9) C13 0.0119(12) 0.0134(12) 0.0158(13) 0.0000(11) 0.0021(10) -0.0010(9) C14 0.0176(13) 0.0119(12) 0.0239(15) -0.0010(12) 0.0006(11) 0.0001(10) C15 0.0166(13) 0.0180(13) 0.0201(14) 0.0017(12) -0.0004(11) 0.0026(10) C16 0.0136(13) 0.0169(13) 0.0207(14) -0.0006(12) 0.0001(11) -0.0009(10) C17 0.0129(12) 0.0142(12) 0.0210(14) -0.0017(11) 0.0002(10) 0.0005(9) C18 0.0114(12) 0.0144(12) 0.0184(14) 0.0012(11) 0.0020(10) 0.0004(9) C19 0.0116(12) 0.0150(13) 0.0203(15) -0.0029(11) 0.0023(11) 0.0007(9) C20 0.0204(15) 0.0236(15) 0.0372(19) 0.0028(14) -0.0115(13) 0.0016(11) Co1 0.0148(3) 0.0187(3) 0.0159(3) 0.0030(2) 0.0031(2) -0.00079(19) Co2 0.01557(18) 0.01707(19) 0.01579(19) -0.00059(15) 0.00250(14) -0.00303(13) N1 0.0166(12) 0.0198(12) 0.0219(13) 0.0032(10) -0.0020(10) -0.0028(9) N2 0.0245(14) 0.0217(13) 0.0304(15) 0.0032(12) -0.0044(11) -0.0104(10) N3 0.0160(12) 0.0191(12) 0.0280(14) 0.0016(11) -0.0042(10) 0.0014(9) N4 0.0228(13) 0.0143(11) 0.0394(17) 0.0023(12) -0.0105(12) 0.0039(9) Nd1 0.01145(8) 0.00914(8) 0.01427(9) 0.00005(5) -0.00068(6) -0.00043(4) O1 0.0233(11) 0.0221(11) 0.0238(12) -0.0010(9) 0.0083(9) -0.0062(8) O2 0.0181(10) 0.0365(12) 0.0171(10) 0.0021(10) 0.0022(8) -0.0018(8) O3 0.0245(11) 0.0252(10) 0.0188(11) -0.0032(9) 0.0061(9) -0.0061(8) O4 0.0225(11) 0.0391(12) 0.0212(12) -0.0043(10) 0.0056(9) -0.0112(9) O5 0.0163(10) 0.0205(10) 0.0208(11) -0.0016(9) 0.0031(8) -0.0019(8) O6 0.0258(11) 0.0165(10) 0.0195(11) -0.0042(9) 0.0001(9) 0.0008(8) O7 0.0271(11) 0.0192(10) 0.0168(10) 0.0001(9) -0.0038(8) -0.0009(8) O8 0.0403(13) 0.0113(9) 0.0190(11) 0.0022(9) -0.0026(9) 0.0023(8) O9 0.0294(12) 0.0282(11) 0.0155(10) -0.0031(9) 0.0039(9) -0.0067(9) O10 0.0137(10) 0.0150(9) 0.0251(11) 0.0012(9) 0.0025(8) -0.0033(7) O11 0.0114(9) 0.0151(9) 0.0246(11) -0.0011(9) -0.0002(8) 0.0002(7) O12 0.0132(10) 0.0131(9) 0.0400(13) -0.0012(9) 0.0009(9) 0.0010(7) O13 0.0342(13) 0.0266(11) 0.0297(13) 0.0038(11) 0.0076(10) 0.0043(9) O14 0.092(3) 0.093(3) 0.066(3) -0.042(2) 0.022(2) -0.028(2) O15 0.109(4) 0.154(5) 0.077(3) 0.005(3) -0.022(3) -0.059(4) O16 0.068(3) 0.074(3) 0.125(5) -0.013(3) 0.000(3) -0.005(2) _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 O4 1.245(3) . ? C1 O2 1.258(4) . ? C1 C2 1.551(4) . ? C2 O3 1.242(4) . ? C2 O1 1.265(3) . ? C3 O6 1.246(3) . ? C3 O5 1.257(3) . ? C3 C4 1.499(4) . ? C4 C5 1.387(4) . ? C4 C9 1.415(4) . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 N1 1.387(4) . ? C6 C7 1.406(4) . ? C7 N2 1.377(4) . ? C7 C8 1.380(4) . ? C8 C9 1.386(4) . ? C8 H8 0.9500 . ? C9 C10 1.486(4) . ? C10 O7 1.257(4) . ? C10 O8 1.267(3) . ? C11 N1 1.318(4) . ? C11 N2 1.340(4) . ? C11 H11 0.9500 . ? C12 O9 1.237(3) . ? C12 O10 1.283(3) . ? C12 C13 1.508(4) . ? C13 C14 1.384(4) . ? C13 C18 1.429(4) . ? C14 C15 1.391(4) . ? C14 H14 0.9500 . ? C15 N4 1.377(4) . ? C15 C16 1.408(4) . ? C16 C17 1.389(4) . ? C16 N3 1.394(4) . ? C17 C18 1.380(4) . ? C17 H17 0.9500 . ? C18 C19 1.485(4) . ? C19 O12 1.265(3) . ? C19 O11 1.278(3) . ? C19 Nd1 2.891(3) 2_646 ? C20 N3 1.316(4) . ? C20 N4 1.352(4) . ? C20 H20 0.9500 . ? Co1 O2 2.104(2) . ? Co1 O2 2.104(2) 3_557 ? Co1 N1 2.112(2) 1_455 ? Co1 N1 2.112(2) 3_657 ? Co1 O1 2.125(2) . ? Co1 O1 2.125(2) 3_557 ? Co2 O5 2.017(2) . ? Co2 O9 2.079(2) . ? Co2 O3 2.097(2) . ? Co2 O4 2.106(2) . ? Co2 N3 2.147(3) 2_556 ? Co2 O13 2.187(2) . ? N1 Co1 2.112(2) 1_655 ? N2 H2 0.8800 . ? N3 Co2 2.147(3) 2_546 ? N4 H4 0.8800 . ? Nd1 O6 2.338(2) . ? Nd1 O7 2.355(2) 2_646 ? Nd1 O8 2.381(2) 1_545 ? Nd1 O12 2.428(2) 2_656 ? Nd1 O11 2.4298(19) . ? Nd1 O10 2.519(2) 2_646 ? Nd1 O10 2.603(2) . ? Nd1 O11 2.641(2) 2_656 ? Nd1 C19 2.891(3) 2_656 ? Nd1 Nd1 4.0743(7) 2_646 ? Nd1 Nd1 4.0743(7) 2_656 ? O7 Nd1 2.355(2) 2_656 ? O8 Nd1 2.381(2) 1_565 ? O10 Nd1 2.5192(19) 2_656 ? O11 Nd1 2.6405(19) 2_646 ? O12 Nd1 2.428(2) 2_646 ? O13 H13A 0.8456 . ? O13 H13B 0.8492 . ? O14 H14A 0.8514 . ? O14 H14B 0.8530 . ? O15 H15B 0.8516 . ? O15 H15A 0.8507 . ? O16 H16A 0.8552 . ? O16 H16B 0.8511 . ? 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 O4 C1 O2 126.0(3) . . ? O4 C1 C2 116.0(3) . . ? O2 C1 C2 118.0(2) . . ? O3 C2 O1 125.9(3) . . ? O3 C2 C1 117.3(2) . . ? O1 C2 C1 116.8(3) . . ? O6 C3 O5 125.3(3) . . ? O6 C3 C4 119.0(2) . . ? O5 C3 C4 115.4(2) . . ? C5 C4 C9 121.5(3) . . ? C5 C4 C3 117.2(2) . . ? C9 C4 C3 121.1(2) . . ? C6 C5 C4 117.3(3) . . ? C6 C5 H5 121.4 . . ? C4 C5 H5 121.4 . . ? C5 C6 N1 130.2(3) . . ? C5 C6 C7 120.7(3) . . ? N1 C6 C7 109.0(3) . . ? N2 C7 C8 132.6(3) . . ? N2 C7 C6 105.0(3) . . ? C8 C7 C6 122.4(3) . . ? C7 C8 C9 117.0(3) . . ? C7 C8 H8 121.5 . . ? C9 C8 H8 121.5 . . ? C8 C9 C4 121.0(3) . . ? C8 C9 C10 119.2(3) . . ? C4 C9 C10 119.7(3) . . ? O7 C10 O8 124.1(3) . . ? O7 C10 C9 118.3(2) . . ? O8 C10 C9 117.6(3) . . ? N1 C11 N2 112.9(3) . . ? N1 C11 H11 123.5 . . ? N2 C11 H11 123.5 . . ? O9 C12 O10 124.7(3) . . ? O9 C12 C13 115.6(2) . . ? O10 C12 C13 119.8(2) . . ? C14 C13 C18 120.6(3) . . ? C14 C13 C12 118.1(2) . . ? C18 C13 C12 120.7(2) . . ? C13 C14 C15 117.0(3) . . ? C13 C14 H14 121.5 . . ? C15 C14 H14 121.5 . . ? N4 C15 C14 132.2(3) . . ? N4 C15 C16 104.9(3) . . ? C14 C15 C16 122.8(3) . . ? C17 C16 N3 130.9(3) . . ? C17 C16 C15 119.7(3) . . ? N3 C16 C15 109.4(2) . . ? C18 C17 C16 118.4(3) . . ? C18 C17 H17 120.8 . . ? C16 C17 H17 120.8 . . ? C17 C18 C13 121.3(2) . . ? C17 C18 C19 117.5(2) . . ? C13 C18 C19 121.1(2) . . ? O12 C19 O11 119.7(2) . . ? O12 C19 C18 119.8(3) . . ? O11 C19 C18 120.4(2) . . ? O12 C19 Nd1 56.26(13) . 2_646 ? O11 C19 Nd1 65.88(14) . 2_646 ? C18 C19 Nd1 160.5(2) . 2_646 ? N3 C20 N4 113.0(3) . . ? N3 C20 H20 123.5 . . ? N4 C20 H20 123.5 . . ? O2 Co1 O2 180.000(1) . 3_557 ? O2 Co1 N1 84.44(9) . 1_455 ? O2 Co1 N1 95.56(9) 3_557 1_455 ? O2 Co1 N1 95.56(9) . 3_657 ? O2 Co1 N1 84.44(9) 3_557 3_657 ? N1 Co1 N1 180.000(1) 1_455 3_657 ? O2 Co1 O1 79.77(9) . . ? O2 Co1 O1 100.23(9) 3_557 . ? N1 Co1 O1 85.54(9) 1_455 . ? N1 Co1 O1 94.46(9) 3_657 . ? O2 Co1 O1 100.23(9) . 3_557 ? O2 Co1 O1 79.77(9) 3_557 3_557 ? N1 Co1 O1 94.46(9) 1_455 3_557 ? N1 Co1 O1 85.54(9) 3_657 3_557 ? O1 Co1 O1 180.000(1) . 3_557 ? O5 Co2 O9 108.25(9) . . ? O5 Co2 O3 162.46(9) . . ? O9 Co2 O3 88.71(9) . . ? O5 Co2 O4 83.89(9) . . ? O9 Co2 O4 166.21(9) . . ? O3 Co2 O4 78.77(9) . . ? O5 Co2 N3 91.00(9) . 2_556 ? O9 Co2 N3 91.18(10) . 2_556 ? O3 Co2 N3 93.15(9) . 2_556 ? O4 Co2 N3 95.22(10) . 2_556 ? O5 Co2 O13 89.81(9) . . ? O9 Co2 O13 85.95(9) . . ? O3 Co2 O13 86.88(9) . . ? O4 Co2 O13 87.62(10) . . ? N3 Co2 O13 177.12(10) 2_556 . ? C11 N1 C6 105.3(3) . . ? C11 N1 Co1 126.8(2) . 1_655 ? C6 N1 Co1 127.71(19) . 1_655 ? C11 N2 C7 107.7(3) . . ? C11 N2 H2 126.2 . . ? C7 N2 H2 126.2 . . ? C20 N3 C16 105.0(3) . . ? C20 N3 Co2 123.7(2) . 2_546 ? C16 N3 Co2 130.52(19) . 2_546 ? C20 N4 C15 107.7(2) . . ? C20 N4 H4 126.2 . . ? C15 N4 H4 126.2 . . ? O6 Nd1 O7 139.72(7) . 2_646 ? O6 Nd1 O8 69.36(8) . 1_545 ? O7 Nd1 O8 149.19(8) 2_646 1_545 ? O6 Nd1 O12 84.48(8) . 2_656 ? O7 Nd1 O12 94.42(8) 2_646 2_656 ? O8 Nd1 O12 99.65(8) 1_545 2_656 ? O6 Nd1 O11 116.12(7) . . ? O7 Nd1 O11 76.47(8) 2_646 . ? O8 Nd1 O11 80.08(8) 1_545 . ? O12 Nd1 O11 157.11(7) 2_656 . ? O6 Nd1 O10 136.83(7) . 2_646 ? O7 Nd1 O10 82.28(7) 2_646 2_646 ? O8 Nd1 O10 72.79(7) 1_545 2_646 ? O12 Nd1 O10 82.09(7) 2_656 2_646 ? O11 Nd1 O10 75.94(6) . 2_646 ? O6 Nd1 O10 73.88(7) . . ? O7 Nd1 O10 72.78(7) 2_646 . ? O8 Nd1 O10 120.26(7) 1_545 . ? O12 Nd1 O10 121.90(6) 2_656 . ? O11 Nd1 O10 75.94(6) . . ? O10 Nd1 O10 145.95(4) 2_646 . ? O6 Nd1 O11 74.52(7) . 2_656 ? O7 Nd1 O11 73.75(7) 2_646 2_656 ? O8 Nd1 O11 135.61(7) 1_545 2_656 ? O12 Nd1 O11 51.22(6) 2_656 2_656 ? O11 Nd1 O11 140.60(4) . 2_656 ? O10 Nd1 O11 123.93(6) 2_646 2_656 ? O10 Nd1 O11 71.02(6) . 2_656 ? O6 Nd1 C19 74.24(8) . 2_656 ? O7 Nd1 C19 87.57(8) 2_646 2_656 ? O8 Nd1 C19 116.08(9) 1_545 2_656 ? O12 Nd1 C19 25.67(7) 2_656 2_656 ? O11 Nd1 C19 163.68(8) . 2_656 ? O10 Nd1 C19 105.64(7) 2_646 2_656 ? O10 Nd1 C19 96.26(7) . 2_656 ? O11 Nd1 C19 26.22(7) 2_656 2_656 ? O6 Nd1 Nd1 133.93(5) . 2_646 ? O7 Nd1 Nd1 80.75(5) 2_646 2_646 ? O8 Nd1 Nd1 68.47(5) 1_545 2_646 ? O12 Nd1 Nd1 120.11(5) 2_656 2_646 ? O11 Nd1 Nd1 38.33(4) . 2_646 ? O10 Nd1 Nd1 38.02(5) 2_646 2_646 ? O10 Nd1 Nd1 113.37(5) . 2_646 ? O11 Nd1 Nd1 151.52(5) 2_656 2_646 ? C19 Nd1 Nd1 142.81(5) 2_656 2_646 ? O6 Nd1 Nd1 74.36(5) . 2_656 ? O7 Nd1 Nd1 65.41(5) 2_646 2_656 ? O8 Nd1 Nd1 142.44(5) 1_545 2_656 ? O12 Nd1 Nd1 86.02(5) 2_656 2_656 ? O11 Nd1 Nd1 108.30(5) . 2_656 ? O10 Nd1 Nd1 144.52(5) 2_646 2_656 ? O10 Nd1 Nd1 36.59(4) . 2_656 ? O11 Nd1 Nd1 34.80(4) 2_656 2_656 ? C19 Nd1 Nd1 60.78(6) 2_656 2_656 ? Nd1 Nd1 Nd1 139.192(16) 2_646 2_656 ? C2 O1 Co1 108.58(19) . . ? C1 O2 Co1 108.31(19) . . ? C2 O3 Co2 113.68(19) . . ? C1 O4 Co2 114.1(2) . . ? C3 O5 Co2 128.25(19) . . ? C3 O6 Nd1 160.7(2) . . ? C10 O7 Nd1 135.80(19) . 2_656 ? C10 O8 Nd1 132.27(19) . 1_565 ? C12 O9 Co2 140.5(2) . . ? C12 O10 Nd1 149.72(17) . 2_656 ? C12 O10 Nd1 104.89(16) . . ? Nd1 O10 Nd1 105.39(7) 2_656 . ? C19 O11 Nd1 162.47(18) . . ? C19 O11 Nd1 87.90(15) . 2_646 ? Nd1 O11 Nd1 106.87(7) . 2_646 ? C19 O12 Nd1 98.07(16) . 2_646 ? Co2 O13 H13A 115.1 . . ? Co2 O13 H13B 114.3 . . ? H13A O13 H13B 107.0 . . ? H14A O14 H14B 103.7 . . ? H15B O15 H15A 110.1 . . ? H16A O16 H16B 115.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 C1 C2 O3 3.3(4) . . . . ? O2 C1 C2 O3 -176.5(3) . . . . ? O4 C1 C2 O1 -177.3(3) . . . . ? O2 C1 C2 O1 2.8(4) . . . . ? O6 C3 C4 C5 -73.0(4) . . . . ? O5 C3 C4 C5 101.4(3) . . . . ? O6 C3 C4 C9 112.2(3) . . . . ? O5 C3 C4 C9 -73.5(3) . . . . ? C9 C4 C5 C6 -0.4(4) . . . . ? C3 C4 C5 C6 -175.2(3) . . . . ? C4 C5 C6 N1 179.5(3) . . . . ? C4 C5 C6 C7 -2.5(4) . . . . ? C5 C6 C7 N2 -175.7(3) . . . . ? N1 C6 C7 N2 2.6(3) . . . . ? C5 C6 C7 C8 3.7(5) . . . . ? N1 C6 C7 C8 -177.9(3) . . . . ? N2 C7 C8 C9 177.6(3) . . . . ? C6 C7 C8 C9 -1.7(5) . . . . ? C7 C8 C9 C4 -1.2(4) . . . . ? C7 C8 C9 C10 -178.0(3) . . . . ? C5 C4 C9 C8 2.3(4) . . . . ? C3 C4 C9 C8 176.9(3) . . . . ? C5 C4 C9 C10 179.1(3) . . . . ? C3 C4 C9 C10 -6.3(4) . . . . ? C8 C9 C10 O7 162.0(3) . . . . ? C4 C9 C10 O7 -14.8(4) . . . . ? C8 C9 C10 O8 -17.5(4) . . . . ? C4 C9 C10 O8 165.6(3) . . . . ? O9 C12 C13 C14 102.8(3) . . . . ? O10 C12 C13 C14 -77.5(3) . . . . ? O9 C12 C13 C18 -68.9(3) . . . . ? O10 C12 C13 C18 110.8(3) . . . . ? C18 C13 C14 C15 3.4(4) . . . . ? C12 C13 C14 C15 -168.3(2) . . . . ? C13 C14 C15 N4 178.0(3) . . . . ? C13 C14 C15 C16 0.4(4) . . . . ? N4 C15 C16 C17 178.0(3) . . . . ? C14 C15 C16 C17 -3.9(4) . . . . ? N4 C15 C16 N3 -0.8(3) . . . . ? C14 C15 C16 N3 177.4(3) . . . . ? N3 C16 C17 C18 -178.3(3) . . . . ? C15 C16 C17 C18 3.2(4) . . . . ? C16 C17 C18 C13 0.6(4) . . . . ? C16 C17 C18 C19 -175.1(3) . . . . ? C14 C13 C18 C17 -4.0(4) . . . . ? C12 C13 C18 C17 167.4(2) . . . . ? C14 C13 C18 C19 171.4(3) . . . . ? C12 C13 C18 C19 -17.1(4) . . . . ? C17 C18 C19 O12 -14.9(4) . . . . ? C13 C18 C19 O12 169.5(3) . . . . ? C17 C18 C19 O11 161.3(3) . . . . ? C13 C18 C19 O11 -14.4(4) . . . . ? C17 C18 C19 Nd1 57.6(6) . . . 2_646 ? C13 C18 C19 Nd1 -118.0(5) . . . 2_646 ? N2 C11 N1 C6 0.7(4) . . . . ? N2 C11 N1 Co1 -174.1(2) . . . 1_655 ? C5 C6 N1 C11 176.1(3) . . . . ? C7 C6 N1 C11 -2.1(3) . . . . ? C5 C6 N1 Co1 -9.2(5) . . . 1_655 ? C7 C6 N1 Co1 172.6(2) . . . 1_655 ? N1 C11 N2 C7 1.0(4) . . . . ? C8 C7 N2 C11 178.4(3) . . . . ? C6 C7 N2 C11 -2.2(3) . . . . ? N4 C20 N3 C16 0.4(4) . . . . ? N4 C20 N3 Co2 171.4(2) . . . 2_546 ? C17 C16 N3 C20 -178.4(3) . . . . ? C15 C16 N3 C20 0.2(3) . . . . ? C17 C16 N3 Co2 11.5(5) . . . 2_546 ? C15 C16 N3 Co2 -169.9(2) . . . 2_546 ? N3 C20 N4 C15 -0.9(4) . . . . ? C14 C15 N4 C20 -176.9(3) . . . . ? C16 C15 N4 C20 1.0(4) . . . . ? O3 C2 O1 Co1 -161.9(3) . . . . ? C1 C2 O1 Co1 18.8(3) . . . . ? O2 Co1 O1 C2 -23.67(19) . . . . ? O2 Co1 O1 C2 156.33(19) 3_557 . . . ? N1 Co1 O1 C2 61.5(2) 1_455 . . . ? N1 Co1 O1 C2 -118.5(2) 3_657 . . . ? O4 C1 O2 Co1 157.2(3) . . . . ? C2 C1 O2 Co1 -22.9(3) . . . . ? N1 Co1 O2 C1 -61.4(2) 1_455 . . . ? N1 Co1 O2 C1 118.6(2) 3_657 . . . ? O1 Co1 O2 C1 25.0(2) . . . . ? O1 Co1 O2 C1 -155.0(2) 3_557 . . . ? O1 C2 O3 Co2 176.1(2) . . . . ? C1 C2 O3 Co2 -4.6(3) . . . . ? O5 Co2 O3 C2 12.3(4) . . . . ? O9 Co2 O3 C2 177.7(2) . . . . ? O4 Co2 O3 C2 3.5(2) . . . . ? N3 Co2 O3 C2 -91.2(2) 2_556 . . . ? O13 Co2 O3 C2 91.7(2) . . . . ? O2 C1 O4 Co2 179.7(2) . . . . ? C2 C1 O4 Co2 -0.1(3) . . . . ? O5 Co2 O4 C1 -179.0(2) . . . . ? O9 Co2 O4 C1 -26.8(5) . . . . ? O3 Co2 O4 C1 -1.7(2) . . . . ? N3 Co2 O4 C1 90.5(2) 2_556 . . . ? O13 Co2 O4 C1 -89.0(2) . . . . ? O6 C3 O5 Co2 4.7(4) . . . . ? C4 C3 O5 Co2 -169.20(18) . . . . ? O9 Co2 O5 C3 -37.7(3) . . . . ? O3 Co2 O5 C3 127.0(3) . . . . ? O4 Co2 O5 C3 135.6(2) . . . . ? N3 Co2 O5 C3 -129.2(2) 2_556 . . . ? O13 Co2 O5 C3 48.0(2) . . . . ? O5 C3 O6 Nd1 82.2(6) . . . . ? C4 C3 O6 Nd1 -104.1(6) . . . . ? O7 Nd1 O6 C3 6.0(6) 2_646 . . . ? O8 Nd1 O6 C3 -161.2(6) 1_545 . . . ? O12 Nd1 O6 C3 96.3(6) 2_656 . . . ? O11 Nd1 O6 C3 -94.2(6) . . . . ? O10 Nd1 O6 C3 168.5(5) 2_646 . . . ? O10 Nd1 O6 C3 -29.2(6) . . . . ? O11 Nd1 O6 C3 45.1(6) 2_656 . . . ? C19 Nd1 O6 C3 72.3(6) 2_656 . . . ? Nd1 Nd1 O6 C3 -136.4(6) 2_646 . . . ? Nd1 Nd1 O6 C3 8.9(6) 2_656 . . . ? O8 C10 O7 Nd1 54.4(4) . . . 2_656 ? C9 C10 O7 Nd1 -125.1(2) . . . 2_656 ? O7 C10 O8 Nd1 -40.4(4) . . . 1_565 ? C9 C10 O8 Nd1 139.1(2) . . . 1_565 ? O10 C12 O9 Co2 32.3(5) . . . . ? C13 C12 O9 Co2 -148.0(2) . . . . ? O5 Co2 O9 C12 -33.7(3) . . . . ? O3 Co2 O9 C12 150.9(3) . . . . ? O4 Co2 O9 C12 175.4(3) . . . . ? N3 Co2 O9 C12 57.7(3) 2_556 . . . ? O13 Co2 O9 C12 -122.2(3) . . . . ? O9 C12 O10 Nd1 -107.0(4) . . . 2_656 ? C13 C12 O10 Nd1 73.3(4) . . . 2_656 ? O9 C12 O10 Nd1 74.1(3) . . . . ? C13 C12 O10 Nd1 -105.6(2) . . . . ? O6 Nd1 O10 C12 -95.27(18) . . . . ? O7 Nd1 O10 C12 107.67(19) 2_646 . . . ? O8 Nd1 O10 C12 -41.7(2) 1_545 . . . ? O12 Nd1 O10 C12 -167.94(17) 2_656 . . . ? O11 Nd1 O10 C12 27.75(17) . . . . ? O10 Nd1 O10 C12 62.89(17) 2_646 . . . ? O11 Nd1 O10 C12 -174.06(19) 2_656 . . . ? C19 Nd1 O10 C12 -166.84(18) 2_656 . . . ? Nd1 Nd1 O10 C12 36.18(19) 2_646 . . . ? Nd1 Nd1 O10 C12 179.4(2) 2_656 . . . ? O6 Nd1 O10 Nd1 85.32(9) . . . 2_656 ? O7 Nd1 O10 Nd1 -71.74(8) 2_646 . . 2_656 ? O8 Nd1 O10 Nd1 138.92(8) 1_545 . . 2_656 ? O12 Nd1 O10 Nd1 12.65(11) 2_656 . . 2_656 ? O11 Nd1 O10 Nd1 -151.67(9) . . . 2_656 ? O10 Nd1 O10 Nd1 -116.52(12) 2_646 . . 2_656 ? O11 Nd1 O10 Nd1 6.53(7) 2_656 . . 2_656 ? C19 Nd1 O10 Nd1 13.75(9) 2_656 . . 2_656 ? Nd1 Nd1 O10 Nd1 -143.24(5) 2_646 . . 2_656 ? O12 C19 O11 Nd1 165.0(5) . . . . ? C18 C19 O11 Nd1 -11.1(8) . . . . ? Nd1 C19 O11 Nd1 148.0(6) 2_646 . . . ? O12 C19 O11 Nd1 17.0(3) . . . 2_646 ? C18 C19 O11 Nd1 -159.1(2) . . . 2_646 ? O6 Nd1 O11 C19 84.9(6) . . . . ? O7 Nd1 O11 C19 -54.2(6) 2_646 . . . ? O8 Nd1 O11 C19 145.9(6) 1_545 . . . ? O12 Nd1 O11 C19 -122.8(6) 2_656 . . . ? O10 Nd1 O11 C19 -139.5(6) 2_646 . . . ? O10 Nd1 O11 C19 21.1(6) . . . . ? O11 Nd1 O11 C19 -12.5(6) 2_656 . . . ? C19 Nd1 O11 C19 -41.8(8) 2_656 . . . ? Nd1 Nd1 O11 C19 -146.4(7) 2_646 . . . ? Nd1 Nd1 O11 C19 3.7(6) 2_656 . . . ? O6 Nd1 O11 Nd1 -128.73(8) . . . 2_646 ? O7 Nd1 O11 Nd1 92.16(8) 2_646 . . 2_646 ? O8 Nd1 O11 Nd1 -67.71(8) 1_545 . . 2_646 ? O12 Nd1 O11 Nd1 23.6(2) 2_656 . . 2_646 ? O10 Nd1 O11 Nd1 6.87(7) 2_646 . . 2_646 ? O10 Nd1 O11 Nd1 167.47(9) . . . 2_646 ? O11 Nd1 O11 Nd1 133.87(9) 2_656 . . 2_646 ? C19 Nd1 O11 Nd1 104.6(2) 2_656 . . 2_646 ? Nd1 Nd1 O11 Nd1 150.13(5) 2_656 . . 2_646 ? O11 C19 O12 Nd1 -18.7(3) . . . 2_646 ? C18 C19 O12 Nd1 157.4(2) . . . 2_646 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O16 H16B O2 0.85 2.56 3.278(5) 143.0 1_565 O16 H16A O14 0.86 2.15 2.988(6) 168.1 . O15 H15A O2 0.85 2.41 2.921(5) 119.4 3_667 O14 H14B O16 0.85 2.29 3.131(7) 169.9 3_667 O14 H14A O4 0.85 2.57 3.040(4) 115.8 . O14 H14A O5 0.85 2.04 2.847(4) 158.2 . O13 H13B O6 0.85 2.56 3.063(3) 119.4 . O13 H13B O8 0.85 2.13 2.972(3) 169.3 1_545 O13 H13A O15 0.85 2.04 2.869(6) 165.3 1_545 N4 H4 O9 0.88 2.55 3.331(3) 148.9 2_556 N4 H4 O3 0.88 2.30 3.005(3) 136.9 2_556 N2 H2 O16 0.88 2.53 3.038(5) 117.2 1_655 N2 H2 O1 0.88 2.04 2.810(3) 145.8 1_665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.120 _refine_diff_density_min -1.081 _refine_diff_density_rms 0.142