# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Hegen Zheng' _publ_contact_author_email ZHENGHG@NJU.EDU.CN _publ_section_title ; Eight new complexes based on flexible multicarboxylate ligands: synthesis, structures, and properties ; loop_ _publ_author_name 'Hegen Zheng' 'Zi-Jian Guo' 'Chang-Chun Ji' 'Jing Li' 'Yi-Zhi Li' # Attachment '1.cif' data_90522bm _database_code_depnum_ccdc_archive 'CCDC 755008' #TrackingRef '1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O8 Zn' _chemical_formula_sum 'C14 H14 O8 Zn' _chemical_formula_weight 375.62 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.285(2) _cell_length_b 7.587(2) _cell_length_c 12.792(4) _cell_angle_alpha 91.046(5) _cell_angle_beta 97.523(5) _cell_angle_gamma 95.694(5) _cell_volume 697.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1511 _cell_measurement_theta_min 2.699 _cell_measurement_theta_max 27.120 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.789 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 1.804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.679 _exptl_absorpt_correction_T_max 0.723 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3497 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_sigmaI/netI 0.0600 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2417 _reflns_number_gt 2051 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0422P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2417 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0932 _refine_ls_wR_factor_gt 0.0908 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _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 0.6860(5) 0.5162(5) 0.1638(3) 0.0289(8) Uani 1 1 d . . . C2 C 0.7863(4) 0.5767(5) 0.2708(3) 0.0306(8) Uani 1 1 d . . . H2A H 0.7643 0.6982 0.2854 0.037 Uiso 1 1 calc R . . H2B H 0.7383 0.5033 0.3244 0.037 Uiso 1 1 calc R . . C3 C 1.0895(5) 0.6338(4) 0.3650(3) 0.0291(8) Uani 1 1 d . . . C4 C 1.0239(5) 0.7028(4) 0.4491(3) 0.0309(8) Uani 1 1 d . . . H4 H 0.8964 0.7043 0.4487 0.037 Uiso 1 1 calc R . . C5 C 1.1482(5) 0.7730(4) 0.5378(3) 0.0278(8) Uani 1 1 d . . . C6 C 1.0820(4) 0.8427(4) 0.6274(3) 0.0315(8) Uani 1 1 d . . . H6 H 0.9546 0.8401 0.6293 0.038 Uiso 1 1 calc R . . C7 C 1.2034(5) 0.9134(4) 0.7105(3) 0.0310(8) Uani 1 1 d . . . C8 C 1.3959(5) 0.9156(5) 0.7096(3) 0.0410(10) Uani 1 1 d . . . H8A H 1.4783 0.9647 0.7667 0.049 Uiso 1 1 calc R . . C9 C 1.4613(5) 0.8462(6) 0.6253(3) 0.0470(11) Uani 1 1 d . . . H9 H 1.5892 0.8466 0.6259 0.056 Uiso 1 1 calc R . . C10 C 1.3405(5) 0.7731(5) 0.5364(3) 0.0341(8) Uani 1 1 d . . . C11 C 1.4026(5) 0.6993(6) 0.4471(3) 0.0449(10) Uani 1 1 d . . . H11 H 1.5298 0.6979 0.4455 0.054 Uiso 1 1 calc R . . C12 C 1.2819(5) 0.6304(5) 0.3635(3) 0.0396(9) Uani 1 1 d . . . H12 H 1.3257 0.5812 0.3056 0.047 Uiso 1 1 calc R . . C13 C 0.9613(5) 0.9984(5) 0.8028(3) 0.0317(8) Uani 1 1 d . . . H13A H 0.9012 0.8817 0.8142 0.038 Uiso 1 1 calc R . . H13B H 0.9045 1.0387 0.7358 0.038 Uiso 1 1 calc R . . C14 C 0.9343(5) 1.1248(4) 0.8903(3) 0.0277(8) Uani 1 1 d . . . O1 O 0.5267(3) 0.5598(4) 0.1455(2) 0.0473(7) Uani 1 1 d . . . O2 O 0.7659(3) 0.4271(3) 0.10420(18) 0.0349(6) Uani 1 1 d . . . O3 O 0.9802(3) 0.5655(3) 0.27473(18) 0.0343(6) Uani 1 1 d . . . O4 O 1.1544(3) 0.9885(3) 0.79989(19) 0.0379(6) Uani 1 1 d . . . O5 O 0.7654(3) 1.1496(3) 0.8921(2) 0.0365(6) Uani 1 1 d . . . O6 O 1.0687(3) 1.1956(3) 0.94968(19) 0.0375(6) Uani 1 1 d . . . O7 O 0.8437(3) 0.5476(3) -0.09868(19) 0.0357(6) Uani 1 1 d . . . H7C H 0.8303 0.6307 -0.0557 0.043 Uiso 1 1 d R . . H7B H 0.9606 0.5447 -0.0839 0.043 Uiso 1 1 d R . . O8 O 0.4474(4) 0.1756(4) 0.0050(2) 0.0472(7) Uani 1 1 d U . . H8B H 0.3566 0.0648 0.0059 0.057 Uiso 1 1 d R . . H8C H 0.3381 0.2078 -0.0014 0.057 Uiso 1 1 d R . . Zn1 Zn 0.66687(5) 0.34928(5) -0.04337(3) 0.03147(16) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0275(19) 0.037(2) 0.0213(18) 0.0028(16) 0.0022(15) 0.0001(16) C2 0.0275(18) 0.041(2) 0.0242(19) -0.0030(16) 0.0034(15) 0.0096(16) C3 0.0276(18) 0.039(2) 0.0203(18) -0.0026(15) 0.0003(14) 0.0068(15) C4 0.0216(17) 0.043(2) 0.0279(19) -0.0056(16) 0.0011(15) 0.0072(15) C5 0.0291(18) 0.0323(19) 0.0220(18) -0.0021(15) 0.0022(15) 0.0057(15) C6 0.0227(18) 0.043(2) 0.029(2) -0.0076(16) 0.0032(15) 0.0082(16) C7 0.0325(19) 0.036(2) 0.0258(19) -0.0059(16) 0.0037(15) 0.0086(16) C8 0.030(2) 0.059(3) 0.031(2) -0.0166(19) -0.0015(17) 0.0020(18) C9 0.0228(19) 0.079(3) 0.037(2) -0.019(2) 0.0008(17) 0.0048(19) C10 0.0300(19) 0.048(2) 0.0229(18) -0.0098(16) -0.0001(15) 0.0029(17) C11 0.0220(19) 0.079(3) 0.033(2) -0.015(2) 0.0036(16) 0.0073(19) C12 0.033(2) 0.063(3) 0.024(2) -0.0121(18) 0.0076(16) 0.0101(19) C13 0.0303(19) 0.035(2) 0.029(2) -0.0069(16) 0.0029(15) 0.0069(16) C14 0.031(2) 0.0302(19) 0.0228(18) 0.0000(15) 0.0051(15) 0.0058(15) O1 0.0278(15) 0.078(2) 0.0357(15) 0.0003(14) -0.0042(12) 0.0162(14) O2 0.0286(13) 0.0521(15) 0.0224(13) -0.0130(12) 0.0005(10) 0.0033(11) O3 0.0247(13) 0.0569(16) 0.0208(12) -0.0110(12) -0.0001(10) 0.0086(11) O4 0.0291(13) 0.0548(16) 0.0297(14) -0.0196(12) 0.0010(11) 0.0116(12) O5 0.0302(14) 0.0404(15) 0.0391(15) -0.0152(12) 0.0057(11) 0.0066(11) O6 0.0322(14) 0.0415(15) 0.0368(15) -0.0187(12) -0.0001(12) 0.0045(12) O7 0.0282(13) 0.0461(15) 0.0321(14) -0.0131(12) 0.0010(11) 0.0063(11) O8 0.0277(13) 0.0495(16) 0.063(2) 0.0031(14) 0.0045(12) 0.0015(11) Zn1 0.0253(2) 0.0434(3) 0.0252(2) -0.01188(18) -0.00108(17) 0.00964(18) _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 O1 1.233(4) . ? C1 O2 1.245(4) . ? C1 C2 1.506(4) . ? C2 O3 1.418(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.350(5) . ? C3 O3 1.375(4) . ? C3 C12 1.407(5) . ? C4 C5 1.416(5) . ? C4 H4 0.9300 . ? C5 C10 1.403(5) . ? C5 C6 1.413(5) . ? C6 C7 1.356(5) . ? C6 H6 0.9300 . ? C7 O4 1.372(4) . ? C7 C8 1.402(5) . ? C8 C9 1.354(5) . ? C8 H8A 0.9300 . ? C9 C10 1.412(5) . ? C9 H9 0.9300 . ? C10 C11 1.409(5) . ? C11 C12 1.354(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O4 1.421(4) . ? C13 C14 1.506(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O6 1.229(4) . ? C14 O5 1.266(4) . ? O1 Zn1 1.978(2) 2_665 ? O2 Zn1 1.988(2) . ? O5 Zn1 1.953(2) 1_566 ? O7 Zn1 2.077(2) . ? O7 H7C 0.8500 . ? O7 H7B 0.8500 . ? O8 Zn1 2.132(3) . ? O8 H8B 1.0182 . ? O8 H8C 0.8500 . ? Zn1 O5 1.953(2) 1_544 ? Zn1 O1 1.978(2) 2_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 126.6(3) . . ? O1 C1 C2 114.3(3) . . ? O2 C1 C2 119.2(3) . . ? O3 C2 C1 110.5(3) . . ? O3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? O3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 O3 124.6(3) . . ? C4 C3 C12 120.9(3) . . ? O3 C3 C12 114.5(3) . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C10 C5 C6 119.7(3) . . ? C10 C5 C4 119.1(3) . . ? C6 C5 C4 121.2(3) . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 O4 125.1(3) . . ? C6 C7 C8 120.5(3) . . ? O4 C7 C8 114.4(3) . . ? C9 C8 C7 119.8(3) . . ? C9 C8 H8A 120.1 . . ? C7 C8 H8A 120.1 . . ? C8 C9 C10 121.7(3) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C5 C10 C11 118.5(3) . . ? C5 C10 C9 118.0(3) . . ? C11 C10 C9 123.5(3) . . ? C12 C11 C10 121.6(3) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C3 119.4(3) . . ? C11 C12 H12 120.3 . . ? C3 C12 H12 120.3 . . ? O4 C13 C14 110.0(3) . . ? O4 C13 H13A 109.7 . . ? C14 C13 H13A 109.7 . . ? O4 C13 H13B 109.7 . . ? C14 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? O6 C14 O5 126.4(3) . . ? O6 C14 C13 120.6(3) . . ? O5 C14 C13 113.0(3) . . ? C1 O1 Zn1 147.9(3) . 2_665 ? C1 O2 Zn1 125.7(2) . . ? C3 O3 C2 116.0(3) . . ? C7 O4 C13 116.8(3) . . ? C14 O5 Zn1 127.8(2) . 1_566 ? Zn1 O7 H7C 98.4 . . ? Zn1 O7 H7B 118.7 . . ? H7C O7 H7B 98.6 . . ? Zn1 O8 H8B 158.4 . . ? Zn1 O8 H8C 119.0 . . ? H8B O8 H8C 72.3 . . ? O5 Zn1 O1 109.57(11) 1_544 2_665 ? O5 Zn1 O2 119.41(10) 1_544 . ? O1 Zn1 O2 131.01(11) 2_665 . ? O5 Zn1 O7 96.72(10) 1_544 . ? O1 Zn1 O7 84.39(11) 2_665 . ? O2 Zn1 O7 89.96(10) . . ? O5 Zn1 O8 90.59(11) 1_544 . ? O1 Zn1 O8 86.41(11) 2_665 . ? O2 Zn1 O8 92.69(11) . . ? O7 Zn1 O8 169.76(9) . . ? 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 O7 H7C O6 0.85 1.90 2.671(3) 150.7 2_776 O7 H7B O2 0.85 2.03 2.842(3) 158.5 2_765 O8 H8B O5 1.02 2.29 3.181(4) 145.7 2_666 O8 H8C O6 0.85 1.97 2.777(3) 157.4 1_444 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.499 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.077 # Attachment '2.cif' data_90322cm _database_code_depnum_ccdc_archive 'CCDC 755009' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cd O8' _chemical_formula_sum 'C14 H14 Cd O8' _chemical_formula_weight 422.65 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' Cd Cd -0.8075 1.2024 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9596(9) _cell_length_b 8.2468(11) _cell_length_c 13.2496(18) _cell_angle_alpha 87.769(3) _cell_angle_beta 82.874(2) _cell_angle_gamma 69.443(2) _cell_volume 706.52(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2462 _cell_measurement_theta_min 2.638 _cell_measurement_theta_max 28.292 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.987 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 1.588 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.712 _exptl_absorpt_correction_T_max 0.751 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3552 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2450 _reflns_number_gt 2248 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0653P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2450 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 1.001 _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 0.2305(7) 0.5637(5) 0.1795(3) 0.0250(9) Uani 1 1 d . . . C2 C 0.3091(7) 0.4522(6) 0.2693(3) 0.0286(10) Uani 1 1 d . . . H2A H 0.2198 0.5005 0.3311 0.034 Uiso 1 1 calc R . . H2B H 0.3086 0.3362 0.2600 0.034 Uiso 1 1 calc R . . C3 C 0.6005(7) 0.3709(6) 0.3621(3) 0.0267(9) Uani 1 1 d . . . C4 C 0.7951(7) 0.3802(7) 0.3669(4) 0.0383(12) Uani 1 1 d . . . H4 H 0.8537 0.4342 0.3154 0.046 Uiso 1 1 calc R . . C5 C 0.8985(7) 0.3098(7) 0.4475(4) 0.0394(12) Uani 1 1 d . . . H5 H 1.0285 0.3162 0.4502 0.047 Uiso 1 1 calc R . . C6 C 0.8153(7) 0.2282(6) 0.5262(3) 0.0277(10) Uani 1 1 d . . . C7 C 0.9179(7) 0.1541(7) 0.6115(4) 0.0359(11) Uani 1 1 d . . . H7 H 1.0484 0.1583 0.6157 0.043 Uiso 1 1 calc R . . C8 C 0.8320(7) 0.0774(6) 0.6871(3) 0.0314(10) Uani 1 1 d . . . H8 H 0.9053 0.0256 0.7409 0.038 Uiso 1 1 calc R . . C9 C 0.6334(6) 0.0764(6) 0.6837(3) 0.0256(9) Uani 1 1 d . . . C10 C 0.5284(7) 0.1435(6) 0.6024(3) 0.0293(10) Uani 1 1 d . . . H10 H 0.3974 0.1389 0.6002 0.035 Uiso 1 1 calc R . . C11 C 0.6184(6) 0.2199(6) 0.5218(3) 0.0244(9) Uani 1 1 d . . . C12 C 0.5131(7) 0.2916(6) 0.4369(3) 0.0287(10) Uani 1 1 d . . . H12 H 0.3840 0.2846 0.4321 0.034 Uiso 1 1 calc R . . C13 C 0.3441(6) 0.0318(6) 0.7773(3) 0.0284(10) Uani 1 1 d . . . H13A H 0.3080 -0.0106 0.7178 0.034 Uiso 1 1 calc R . . H13B H 0.2691 0.1554 0.7829 0.034 Uiso 1 1 calc R . . C14 C 0.2839(7) -0.0567(6) 0.8702(3) 0.0254(9) Uani 1 1 d . . . Cd1 Cd -0.11843(4) 0.23328(4) 0.98474(2) 0.02489(15) Uani 1 1 d U . . O1 O -0.0470(5) 0.4054(4) 0.8338(2) 0.0311(7) Uani 1 1 d U . . O2 O 0.3482(5) 0.6225(4) 0.1235(2) 0.0323(7) Uani 1 1 d . . . O3 O 0.5114(5) 0.4456(5) 0.2775(2) 0.0363(8) Uani 1 1 d . . . O4 O 0.5584(4) -0.0001(4) 0.7663(2) 0.0327(8) Uani 1 1 d . . . O5 O 0.4091(5) -0.1642(4) 0.9185(3) 0.0382(8) Uani 1 1 d . . . O6 O 0.0871(4) -0.0200(4) 0.8929(2) 0.0278(7) Uani 1 1 d . . . O7 O 0.1919(6) 0.2354(5) 1.0262(3) 0.0487(9) Uani 1 1 d . . . H7C H 0.2703 0.1444 0.9939 0.058 Uiso 1 1 d R . . H7A H 0.2238 0.2038 1.0855 0.058 Uiso 1 1 d R . . O8 O -0.2352(5) 0.4842(4) 1.0807(2) 0.0350(8) Uani 1 1 d . . . H8C H -0.1119 0.4764 1.0863 0.042 Uiso 1 1 d R . . H8A H -0.2624 0.4801 1.1449 0.042 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 0.028(2) 0.022(2) 0.026(2) 0.0011(17) -0.0052(18) -0.0089(18) C2 0.025(2) 0.037(3) 0.024(2) 0.0123(19) -0.0063(18) -0.0106(19) C3 0.028(2) 0.029(2) 0.024(2) 0.0084(18) -0.0095(18) -0.0093(18) C4 0.028(2) 0.055(3) 0.032(3) 0.017(2) 0.001(2) -0.018(2) C5 0.024(2) 0.065(4) 0.035(3) 0.018(2) -0.010(2) -0.021(2) C6 0.023(2) 0.035(2) 0.026(2) 0.0076(18) -0.0023(18) -0.0118(19) C7 0.022(2) 0.055(3) 0.035(3) 0.015(2) -0.0110(19) -0.018(2) C8 0.028(2) 0.042(3) 0.025(2) 0.011(2) -0.0083(19) -0.013(2) C9 0.024(2) 0.027(2) 0.025(2) 0.0072(17) -0.0021(18) -0.0091(18) C10 0.021(2) 0.039(3) 0.029(2) 0.0125(19) -0.0058(18) -0.0129(19) C11 0.022(2) 0.028(2) 0.023(2) 0.0044(17) -0.0038(17) -0.0084(17) C12 0.021(2) 0.039(3) 0.027(2) 0.0120(19) -0.0054(18) -0.0119(19) C13 0.023(2) 0.034(2) 0.028(2) 0.0123(19) -0.0037(18) -0.0093(19) C14 0.028(2) 0.026(2) 0.023(2) 0.0035(17) -0.0049(18) -0.0108(19) Cd1 0.0240(2) 0.0260(2) 0.0242(2) 0.00989(13) -0.00534(13) -0.00829(14) O1 0.0298(17) 0.0388(19) 0.0280(15) 0.0131(12) -0.0110(13) -0.0148(14) O2 0.0275(16) 0.0411(19) 0.0261(16) 0.0146(14) -0.0047(13) -0.0103(14) O3 0.0291(17) 0.056(2) 0.0294(18) 0.0229(15) -0.0113(14) -0.0208(16) O4 0.0235(16) 0.046(2) 0.0283(17) 0.0196(14) -0.0056(13) -0.0134(14) O5 0.0299(17) 0.046(2) 0.0357(19) 0.0234(16) -0.0075(15) -0.0110(15) O6 0.0266(16) 0.0330(17) 0.0230(15) 0.0059(13) -0.0004(12) -0.0109(13) O7 0.0381(19) 0.043(2) 0.070(3) 0.0089(18) -0.0224(18) -0.0158(16) O8 0.0267(16) 0.049(2) 0.0318(18) -0.0025(15) 0.0018(13) -0.0171(15) _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 O1 1.245(5) 2_566 ? C1 O2 1.248(5) . ? C1 C2 1.512(6) . ? C1 Cd1 2.714(4) 2_566 ? C2 O3 1.407(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C12 1.364(6) . ? C3 O3 1.367(5) . ? C3 C4 1.392(7) . ? C4 C5 1.358(7) . ? C4 H4 0.9300 . ? C5 C6 1.395(7) . ? C5 H5 0.9300 . ? C6 C11 1.404(6) . ? C6 C7 1.414(6) . ? C7 C8 1.352(6) . ? C7 H7 0.9300 . ? C8 C9 1.391(6) . ? C8 H8 0.9300 . ? C9 C10 1.366(6) . ? C9 O4 1.379(5) . ? C10 C11 1.410(6) . ? C10 H10 0.9300 . ? C11 C12 1.414(6) . ? C12 H12 0.9300 . ? C13 O4 1.410(5) . ? C13 C14 1.497(6) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O5 1.227(5) . ? C14 O6 1.292(5) . ? C14 Cd1 2.748(4) 2_557 ? Cd1 O2 2.265(3) 2_566 ? Cd1 O7 2.300(3) . ? Cd1 O8 2.308(3) . ? Cd1 O6 2.317(3) 2_557 ? Cd1 O6 2.358(3) . ? Cd1 O5 2.483(3) 2_557 ? Cd1 O1 2.507(3) . ? Cd1 C1 2.714(4) 2_566 ? Cd1 C14 2.748(4) 2_557 ? O1 C1 1.245(5) 2_566 ? O2 Cd1 2.265(3) 2_566 ? O5 Cd1 2.483(3) 2_557 ? O6 Cd1 2.317(3) 2_557 ? O7 H7C 0.8501 . ? O7 H7A 0.8499 . ? O8 H8C 0.8500 . ? O8 H8A 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 123.0(4) 2_566 . ? O1 C1 C2 117.4(4) 2_566 . ? O2 C1 C2 119.6(4) . . ? O1 C1 Cd1 67.1(2) 2_566 2_566 ? O2 C1 Cd1 55.9(2) . 2_566 ? C2 C1 Cd1 175.5(3) . 2_566 ? O3 C2 C1 109.0(3) . . ? O3 C2 H2A 109.9 . . ? C1 C2 H2A 109.9 . . ? O3 C2 H2B 109.9 . . ? C1 C2 H2B 109.9 . . ? H2A C2 H2B 108.3 . . ? C12 C3 O3 124.8(4) . . ? C12 C3 C4 120.9(4) . . ? O3 C3 C4 114.3(4) . . ? C5 C4 C3 119.4(4) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.9(4) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C5 C6 C11 118.8(4) . . ? C5 C6 C7 123.5(4) . . ? C11 C6 C7 117.7(4) . . ? C8 C7 C6 122.1(4) . . ? C8 C7 H7 119.0 . . ? C6 C7 H7 119.0 . . ? C7 C8 C9 119.6(4) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C9 O4 124.4(4) . . ? C10 C9 C8 120.9(4) . . ? O4 C9 C8 114.7(4) . . ? C9 C10 C11 120.1(4) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C6 C11 C10 119.6(4) . . ? C6 C11 C12 118.9(4) . . ? C10 C11 C12 121.4(4) . . ? C3 C12 C11 120.1(4) . . ? C3 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? O4 C13 C14 110.3(3) . . ? O4 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? O4 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? O5 C14 O6 121.5(4) . . ? O5 C14 C13 123.6(4) . . ? O6 C14 C13 114.8(4) . . ? O5 C14 Cd1 64.6(2) . 2_557 ? O6 C14 Cd1 57.1(2) . 2_557 ? C13 C14 Cd1 167.8(3) . 2_557 ? O2 Cd1 O7 136.81(12) 2_566 . ? O2 Cd1 O8 87.04(12) 2_566 . ? O7 Cd1 O8 80.52(13) . . ? O2 Cd1 O6 137.60(11) 2_566 2_557 ? O7 Cd1 O6 85.59(12) . 2_557 ? O8 Cd1 O6 102.76(12) . 2_557 ? O2 Cd1 O6 103.08(11) 2_566 . ? O7 Cd1 O6 84.31(12) . . ? O8 Cd1 O6 164.75(11) . . ? O6 Cd1 O6 77.57(11) 2_557 . ? O2 Cd1 O5 86.02(10) 2_566 2_557 ? O7 Cd1 O5 133.43(12) . 2_557 ? O8 Cd1 O5 85.87(12) . 2_557 ? O6 Cd1 O5 54.40(10) 2_557 2_557 ? O6 Cd1 O5 105.97(11) . 2_557 ? O2 Cd1 O1 54.36(10) 2_566 . ? O7 Cd1 O1 83.96(12) . . ? O8 Cd1 O1 88.65(11) . . ? O6 Cd1 O1 163.04(11) 2_557 . ? O6 Cd1 O1 88.12(10) . . ? O5 Cd1 O1 140.25(10) 2_557 . ? O2 Cd1 C1 27.15(12) 2_566 2_566 ? O7 Cd1 C1 110.50(13) . 2_566 ? O8 Cd1 C1 87.33(12) . 2_566 ? O6 Cd1 C1 162.43(12) 2_557 2_566 ? O6 Cd1 C1 96.48(12) . 2_566 ? O5 Cd1 C1 113.10(12) 2_557 2_566 ? O1 Cd1 C1 27.21(11) . 2_566 ? O2 Cd1 C14 111.85(12) 2_566 2_557 ? O7 Cd1 C14 110.02(13) . 2_557 ? O8 Cd1 C14 93.16(12) . 2_557 ? O6 Cd1 C14 27.95(11) 2_557 2_557 ? O6 Cd1 C14 93.57(12) . 2_557 ? O5 Cd1 C14 26.53(12) 2_557 2_557 ? O1 Cd1 C14 166.02(12) . 2_557 ? C1 Cd1 C14 138.98(13) 2_566 2_557 ? C1 O1 Cd1 85.7(2) 2_566 . ? C1 O2 Cd1 96.9(3) . 2_566 ? C3 O3 C2 118.3(3) . . ? C9 O4 C13 116.0(3) . . ? C14 O5 Cd1 88.8(3) . 2_557 ? C14 O6 Cd1 94.9(2) . 2_557 ? C14 O6 Cd1 121.2(3) . . ? Cd1 O6 Cd1 102.43(11) 2_557 . ? Cd1 O7 H7C 98.0 . . ? Cd1 O7 H7A 118.4 . . ? H7C O7 H7A 98.4 . . ? Cd1 O8 H8C 91.0 . . ? Cd1 O8 H8A 120.2 . . ? H8C O8 H8A 91.3 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7C O5 0.85 2.58 3.392(5) 161.2 . O7 H7C O6 0.85 2.65 3.126(5) 116.6 . O8 H8C O7 0.85 2.41 2.978(5) 124.7 . O8 H8C O1 0.85 2.10 2.803(4) 139.3 2_567 O8 H8A O3 0.85 2.29 3.033(4) 146.5 1_456 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.575 _refine_diff_density_min -0.668 _refine_diff_density_rms 0.170 # Attachment '3.cif' data_90429bm _database_code_depnum_ccdc_archive 'CCDC 755010' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H16 Co O9' _chemical_formula_sum 'C14 H16 Co O9' _chemical_formula_weight 387.20 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' Co Co 0.3494 0.9721 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.6809(9) _cell_length_b 5.7625(11) _cell_length_c 26.781(5) _cell_angle_alpha 87.236(4) _cell_angle_beta 89.406(3) _cell_angle_gamma 84.635(3) _cell_volume 718.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1047 _cell_measurement_theta_min 2.528 _cell_measurement_theta_max 27.015 _exptl_crystal_description block _exptl_crystal_colour purple _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.790 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 398 _exptl_absorpt_coefficient_mu 1.245 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.713 _exptl_absorpt_correction_T_max 0.760 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3869 _diffrn_reflns_av_R_equivalents 0.0534 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2733 _reflns_number_gt 2169 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0463P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2733 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1042 _refine_ls_wR_factor_gt 0.0994 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.000 _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 O8 O 1.2610(5) 1.1551(4) 0.04941(9) 0.0275(5) Uani 1 1 d . . . O7 O 0.7376(5) 1.3077(4) -0.00148(9) 0.0290(6) Uani 1 1 d . . . O5 O 1.0550(5) 0.5665(4) 0.09126(9) 0.0312(6) Uani 1 1 d . . . C14 C 0.8425(7) 0.7137(5) 0.09387(12) 0.0239(7) Uani 1 1 d . . . O6 O 0.7663(5) 0.8729(4) 0.06155(8) 0.0274(5) Uani 1 1 d . . . Co2 Co 1.0000 1.0000 0.0000 0.02161(19) Uani 1 2 d S . . Co1 Co 0.5000 0.0000 0.5000 0.01969(18) Uani 1 2 d S . . C6 C -0.0897(7) 0.9824(6) 0.26546(13) 0.0258(8) Uani 1 1 d . . . C9 C 0.2947(7) 0.9118(6) 0.18601(12) 0.0247(7) Uani 1 1 d . . . C13 C 0.6628(7) 0.6949(6) 0.14123(12) 0.0261(8) Uani 1 1 d . . . C1 C -0.0139(7) 0.1399(5) 0.43285(12) 0.0218(7) Uani 1 1 d . . . H2A H 0.2660 0.3570 0.4005 0.026 Uiso 1 1 d R . . H2B H 0.1154 0.2168 0.3610 0.026 Uiso 1 1 d R . . C2 C 0.0860(7) 0.3008(6) 0.39146(13) 0.0268(8) Uani 1 1 d . . . C3 C -0.0994(7) 0.6425(5) 0.34297(12) 0.0246(7) Uani 1 1 d . . . C4 C -0.2927(7) 0.8444(5) 0.34335(13) 0.0281(8) Uani 1 1 d . . . H4 H -0.4246 0.8645 0.3693 0.034 Uiso 1 1 calc R . . C5 C -0.2862(7) 1.0095(6) 0.30575(13) 0.0307(8) Uani 1 1 d . . . H5 H -0.4132 1.1435 0.3064 0.037 Uiso 1 1 calc R . . C7 C -0.0757(8) 1.1519(6) 0.22613(13) 0.0333(9) Uani 1 1 d . . . H7 H -0.1971 1.2891 0.2266 0.040 Uiso 1 1 calc R . . C8 C 0.1127(8) 1.1190(6) 0.18728(13) 0.0319(8) Uani 1 1 d . . . H8 H 0.1203 1.2336 0.1618 0.038 Uiso 1 1 calc R . . C10 C 0.2911(7) 0.7455(6) 0.22365(13) 0.0273(8) Uani 1 1 d . . . H10 H 0.4154 0.6101 0.2226 0.033 Uiso 1 1 calc R . . C11 C 0.0984(7) 0.7770(5) 0.26480(12) 0.0231(7) Uani 1 1 d . . . C12 C 0.0936(7) 0.6095(6) 0.30480(12) 0.0279(8) Uani 1 1 d . . . H12 H 0.2220 0.4761 0.3052 0.034 Uiso 1 1 calc R . . H13A H 0.5565 0.5586 0.1407 0.034 Uiso 1 1 d R . . H13B H 0.7858 0.6792 0.1702 0.034 Uiso 1 1 d R . . O1 O 0.1613(4) -0.0295(4) 0.44706(8) 0.0241(5) Uani 1 1 d . . . O2 O -0.2674(4) 0.1818(4) 0.44897(8) 0.0250(5) Uani 1 1 d . . . O3 O -0.1255(5) 0.4911(4) 0.38353(9) 0.0333(6) Uani 1 1 d . . . O4 O 0.4679(5) 0.8984(4) 0.14429(9) 0.0300(6) Uani 1 1 d . . . H7A H 0.7330 1.3672 -0.0299 0.036 Uiso 1 1 d R . . H7C H 0.5706 1.2645 0.0034 0.036 Uiso 1 1 d R . . H8A H 1.3523 1.0538 0.0668 0.036 Uiso 1 1 d R . . H8B H 1.1797 1.2692 0.0648 0.036 Uiso 1 1 d R . . O9 O 0.7306(5) -0.3169(4) 0.48228(9) 0.0288(6) Uani 1 1 d . . . H9A H 0.6552 -0.3891 0.4597 0.035 Uiso 1 1 d R . . H9C H 0.8874 -0.2777 0.4697 0.035 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 O8 0.0264(13) 0.0207(12) 0.0340(14) 0.0012(10) -0.0004(11) 0.0047(9) O7 0.0229(12) 0.0238(12) 0.0381(14) 0.0073(11) 0.0098(11) 0.0033(9) O5 0.0299(14) 0.0270(13) 0.0340(14) 0.0045(11) 0.0079(11) 0.0079(10) C14 0.0231(18) 0.0224(17) 0.0260(18) 0.0014(14) 0.0002(14) -0.0032(14) O6 0.0227(13) 0.0292(13) 0.0279(13) 0.0085(11) 0.0068(10) 0.0037(10) Co2 0.0183(3) 0.0189(3) 0.0263(4) 0.0035(3) 0.0053(3) 0.0027(2) Co1 0.0161(3) 0.0184(3) 0.0236(4) 0.0033(3) 0.0051(3) 0.0003(2) C6 0.0258(18) 0.0231(17) 0.0280(19) 0.0005(14) 0.0031(15) -0.0003(13) C9 0.0238(18) 0.0284(18) 0.0210(17) 0.0039(14) 0.0050(14) -0.0016(14) C13 0.0266(19) 0.0252(17) 0.0246(18) 0.0076(14) 0.0061(15) 0.0022(14) C1 0.0236(18) 0.0234(17) 0.0191(17) -0.0003(13) 0.0009(14) -0.0058(13) C2 0.0213(18) 0.0314(19) 0.0262(18) 0.0071(15) 0.0048(15) 0.0006(14) C3 0.0271(18) 0.0243(17) 0.0219(17) 0.0042(14) 0.0019(14) -0.0034(14) C4 0.0275(19) 0.0266(18) 0.0291(19) 0.0006(15) 0.0108(15) 0.0015(14) C5 0.030(2) 0.0265(18) 0.034(2) 0.0025(16) 0.0067(16) 0.0068(15) C7 0.039(2) 0.0273(19) 0.031(2) 0.0062(16) 0.0068(17) 0.0100(15) C8 0.041(2) 0.0261(18) 0.0268(19) 0.0069(15) 0.0052(17) -0.0001(15) C10 0.0248(18) 0.0247(18) 0.0311(19) 0.0021(15) 0.0065(15) 0.0022(14) C11 0.0209(17) 0.0238(17) 0.0239(18) 0.0031(14) 0.0023(14) 0.0001(13) C12 0.0257(18) 0.0249(18) 0.031(2) 0.0072(15) 0.0061(15) 0.0066(14) O1 0.0202(12) 0.0238(12) 0.0272(13) 0.0032(10) 0.0031(10) 0.0013(9) O2 0.0175(12) 0.0292(12) 0.0271(13) 0.0054(10) 0.0057(10) 0.0002(9) O3 0.0337(14) 0.0296(13) 0.0323(14) 0.0138(11) 0.0170(12) 0.0102(10) O4 0.0309(14) 0.0277(13) 0.0286(13) 0.0081(11) 0.0100(11) 0.0066(10) O9 0.0251(13) 0.0270(12) 0.0341(14) -0.0041(11) 0.0044(11) -0.0009(10) _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 O8 Co2 2.096(2) . ? O8 H8A 0.8192 . ? O8 H8B 0.8505 . ? O7 Co2 2.059(2) . ? O7 H7A 0.8198 . ? O7 H7C 0.8492 . ? O5 C14 1.249(4) . ? C14 O6 1.260(4) . ? C14 C13 1.520(4) . ? O6 Co2 2.108(2) . ? Co2 O7 2.059(2) 2_775 ? Co2 O8 2.096(2) 2_775 ? Co2 O6 2.108(2) 2_775 ? Co1 O2 2.048(2) 2_556 ? Co1 O2 2.048(2) 1_655 ? Co1 O9 2.105(2) . ? Co1 O9 2.105(2) 2_656 ? Co1 O1 2.162(2) 2_656 ? Co1 O1 2.162(2) . ? C6 C7 1.407(4) . ? C6 C11 1.408(4) . ? C6 C5 1.415(4) . ? C9 C10 1.358(4) . ? C9 O4 1.375(4) . ? C9 C8 1.402(4) . ? C13 O4 1.422(4) . ? C13 H13A 0.9689 . ? C13 H13B 0.9677 . ? C1 O1 1.262(4) . ? C1 O2 1.264(4) . ? C1 C2 1.510(4) . ? C2 O3 1.416(4) . ? C2 H2A 0.9671 . ? C2 H2B 0.9717 . ? C3 C12 1.365(4) . ? C3 O3 1.372(4) . ? C3 C4 1.406(4) . ? C4 C5 1.354(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C7 C8 1.365(4) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C10 C11 1.425(4) . ? C10 H10 0.9300 . ? C11 C12 1.409(4) . ? C12 H12 0.9300 . ? O2 Co1 2.048(2) 1_455 ? O9 H9A 0.8488 . ? O9 H9C 0.8499 . ? 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 Co2 O8 H8A 109.7 . . ? Co2 O8 H8B 115.6 . . ? H8A O8 H8B 115.9 . . ? Co2 O7 H7A 109.6 . . ? Co2 O7 H7C 104.0 . . ? H7A O7 H7C 104.5 . . ? O5 C14 O6 126.5(3) . . ? O5 C14 C13 115.4(3) . . ? O6 C14 C13 118.1(3) . . ? C14 O6 Co2 129.0(2) . . ? O7 Co2 O7 180.00(13) 2_775 . ? O7 Co2 O8 87.01(9) 2_775 2_775 ? O7 Co2 O8 92.99(9) . 2_775 ? O7 Co2 O8 92.99(9) 2_775 . ? O7 Co2 O8 87.01(9) . . ? O8 Co2 O8 180.00(10) 2_775 . ? O7 Co2 O6 90.05(8) 2_775 . ? O7 Co2 O6 89.95(8) . . ? O8 Co2 O6 90.59(9) 2_775 . ? O8 Co2 O6 89.41(9) . . ? O7 Co2 O6 89.95(8) 2_775 2_775 ? O7 Co2 O6 90.05(8) . 2_775 ? O8 Co2 O6 89.41(9) 2_775 2_775 ? O8 Co2 O6 90.59(9) . 2_775 ? O6 Co2 O6 180.00(8) . 2_775 ? O2 Co1 O2 180.0 2_556 1_655 ? O2 Co1 O9 88.76(8) 2_556 . ? O2 Co1 O9 91.24(8) 1_655 . ? O2 Co1 O9 91.24(8) 2_556 2_656 ? O2 Co1 O9 88.76(8) 1_655 2_656 ? O9 Co1 O9 180.00(12) . 2_656 ? O2 Co1 O1 92.49(9) 2_556 2_656 ? O2 Co1 O1 87.51(9) 1_655 2_656 ? O9 Co1 O1 85.54(8) . 2_656 ? O9 Co1 O1 94.46(8) 2_656 2_656 ? O2 Co1 O1 87.51(9) 2_556 . ? O2 Co1 O1 92.49(9) 1_655 . ? O9 Co1 O1 94.46(8) . . ? O9 Co1 O1 85.54(8) 2_656 . ? O1 Co1 O1 180.0 2_656 . ? C7 C6 C11 118.9(3) . . ? C7 C6 C5 122.6(3) . . ? C11 C6 C5 118.5(3) . . ? C10 C9 O4 125.4(3) . . ? C10 C9 C8 120.7(3) . . ? O4 C9 C8 113.8(3) . . ? O4 C13 C14 109.5(3) . . ? O4 C13 H13A 109.5 . . ? C14 C13 H13A 109.8 . . ? O4 C13 H13B 109.6 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.5 . . ? O1 C1 O2 125.9(3) . . ? O1 C1 C2 116.6(3) . . ? O2 C1 C2 117.4(3) . . ? O3 C2 C1 108.9(2) . . ? O3 C2 H2A 110.0 . . ? C1 C2 H2A 110.0 . . ? O3 C2 H2B 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.4 . . ? C12 C3 O3 125.3(3) . . ? C12 C3 C4 120.8(3) . . ? O3 C3 C4 113.9(3) . . ? C5 C4 C3 119.8(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C8 C7 C6 121.3(3) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 119.8(3) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C9 C10 C11 120.5(3) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C6 C11 C12 119.5(3) . . ? C6 C11 C10 118.8(3) . . ? C12 C11 C10 121.7(3) . . ? C3 C12 C11 120.1(3) . . ? C3 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C1 O1 Co1 123.3(2) . . ? C1 O2 Co1 130.8(2) . 1_455 ? C3 O3 C2 119.0(2) . . ? C9 O4 C13 116.7(2) . . ? Co1 O9 H9A 114.5 . . ? Co1 O9 H9C 104.7 . . ? H9A O9 H9C 105.1 . . ? 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 O9 H9C O1 0.85 2.07 2.852(3) 151.9 1_655 O9 H9A O2 0.85 2.50 3.063(3) 125.1 1_645 O9 H9A O3 0.85 2.38 2.963(3) 126.7 1_645 O8 H8B O5 0.85 1.92 2.759(3) 167.2 1_565 O8 H8A O4 0.82 2.27 3.000(3) 148.6 1_655 O8 H8A O6 0.82 2.12 2.755(3) 134.3 1_655 O7 H7C O6 0.85 2.56 3.152(3) 127.6 2_675 O7 H7C O8 0.85 2.02 2.792(3) 151.0 1_455 O7 H7A O5 0.82 1.95 2.677(3) 147.1 2_775 _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.610 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.089 # Attachment '4.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 755011' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 Eu N O9' _chemical_formula_sum 'C14 H12 Eu N O9' _chemical_formula_weight 490.21 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' Eu Eu -0.1578 3.6682 '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 _symmetry_space_group_name_Hall '-P 2ybc' 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 14.702(2) _cell_length_b 7.6396(12) _cell_length_c 12.976(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.489(3) _cell_angle_gamma 90.00 _cell_volume 1456.1(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2113 _cell_measurement_theta_min 2.774 _cell_measurement_theta_max 27.117 _exptl_crystal_description flake-like _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 4.363 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.435 _exptl_absorpt_correction_T_max 0.498 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7515 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2853 _reflns_number_gt 2256 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0298P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2853 _refine_ls_number_parameters 226 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0869 _refine_ls_wR_factor_gt 0.0830 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.002 _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 O9 O -0.0359(3) 0.2170(6) -0.1556(3) 0.0219(11) Uani 1 1 d U . . C1 C 0.1382(4) 0.2893(9) 0.1431(5) 0.0163(15) Uani 1 1 d . . . C2 C 0.2305(5) 0.3703(9) 0.1292(6) 0.0257(17) Uani 1 1 d . . . H2A H 0.2715 0.3360 0.1862 0.031 Uiso 1 1 calc R . . H2B H 0.2552 0.3265 0.0661 0.031 Uiso 1 1 calc R . . C3 C 0.3054(5) 0.6429(9) 0.1218(6) 0.0225(16) Uani 1 1 d . . . C4 C 0.3890(5) 0.5689(10) 0.1254(6) 0.0286(18) Uani 1 1 d . . . H4 H 0.3945 0.4477 0.1281 0.034 Uiso 1 1 calc R . . C5 C 0.4685(5) 0.6746(9) 0.1250(6) 0.0227(17) Uani 1 1 d . . . C6 C 0.5563(5) 0.6006(10) 0.1287(6) 0.0280(17) Uani 1 1 d . . . H6 H 0.5628 0.4796 0.1298 0.034 Uiso 1 1 calc R . . C7 C 0.6318(5) 0.7039(9) 0.1306(6) 0.0236(17) Uani 1 1 d . . . C8 C 0.6232(5) 0.8867(9) 0.1269(6) 0.0290(18) Uani 1 1 d . . . H8 H 0.6750 0.9567 0.1275 0.035 Uiso 1 1 calc R . . C9 C 0.5398(5) 0.9611(10) 0.1223(6) 0.0291(19) Uani 1 1 d . . . H9 H 0.5349 1.0825 0.1209 0.035 Uiso 1 1 calc R . . C10 C 0.4594(5) 0.8580(9) 0.1197(6) 0.0264(18) Uani 1 1 d . . . C11 C 0.3706(5) 0.9293(10) 0.1123(6) 0.0315(18) Uani 1 1 d . . . H11 H 0.3636 1.0500 0.1072 0.038 Uiso 1 1 calc R . . C12 C 0.2954(5) 0.8268(10) 0.1124(6) 0.0309(19) Uani 1 1 d . . . H12 H 0.2377 0.8766 0.1064 0.037 Uiso 1 1 calc R . . C13 C 0.7352(5) 0.4620(9) 0.1408(6) 0.0231(17) Uani 1 1 d . . . H13A H 0.7177 0.4095 0.0748 0.028 Uiso 1 1 calc R . . H13B H 0.6979 0.4107 0.1928 0.028 Uiso 1 1 calc R . . C14 C 0.8352(4) 0.4238(10) 0.1672(5) 0.0201(15) Uani 1 1 d . . . Eu1 Eu -0.02034(2) 0.08507(4) 0.19250(3) 0.01489(12) Uani 1 1 d . . . N1 N -0.0434(5) 0.2681(10) -0.0606(5) 0.0445(18) Uani 1 1 d U . . O1 O 0.2254(3) 0.5547(6) 0.1248(4) 0.0314(13) Uani 1 1 d . . . O2 O 0.7199(3) 0.6456(7) 0.1361(4) 0.0324(13) Uani 1 1 d . . . O3 O 0.1298(3) 0.1348(6) 0.1137(4) 0.0224(11) Uani 1 1 d . . . O4 O 0.0759(3) 0.3713(6) 0.1851(4) 0.0197(11) Uani 1 1 d . . . O5 O 0.8510(3) 0.2632(7) 0.1737(4) 0.0291(12) Uani 1 1 d . . . O6 O 0.8915(3) 0.5449(6) 0.1793(4) 0.0240(12) Uani 1 1 d . . . O7 O -0.0391(4) 0.1670(8) 0.0130(4) 0.0383(14) Uani 1 1 d U . . O8 O -0.1407(3) -0.0886(6) 0.1064(3) 0.0236(11) Uani 1 1 d . . . H8A H -0.1549 -0.0663 0.0436 0.028 Uiso 1 1 d R . . H8B H -0.1840 -0.1242 0.1423 0.028 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 O9 0.027(3) 0.015(3) 0.024(2) 0.004(2) 0.003(2) 0.002(2) C1 0.017(4) 0.022(4) 0.010(3) 0.004(3) -0.003(3) -0.004(3) C2 0.025(4) 0.016(4) 0.036(5) 0.000(3) 0.004(3) 0.000(3) C3 0.023(4) 0.015(4) 0.030(4) 0.000(3) 0.002(3) 0.000(3) C4 0.029(4) 0.015(4) 0.042(5) 0.000(4) 0.003(3) -0.004(3) C5 0.023(4) 0.018(4) 0.028(4) 0.000(3) 0.001(3) -0.004(3) C6 0.028(4) 0.015(4) 0.041(5) 0.003(4) -0.001(3) 0.004(3) C7 0.017(4) 0.021(4) 0.032(4) 0.003(3) 0.002(3) 0.002(3) C8 0.025(4) 0.020(4) 0.042(5) 0.006(4) 0.002(3) -0.003(3) C9 0.029(4) 0.014(4) 0.044(5) 0.001(3) 0.006(4) 0.003(3) C10 0.032(4) 0.017(4) 0.030(4) 0.001(3) 0.001(3) 0.001(3) C11 0.035(4) 0.020(4) 0.040(5) 0.000(4) 0.001(4) 0.006(4) C12 0.018(4) 0.029(5) 0.046(5) 0.001(4) 0.003(4) 0.006(3) C13 0.023(4) 0.013(4) 0.034(4) 0.001(3) 0.000(3) 0.002(3) C14 0.020(4) 0.024(4) 0.016(3) -0.004(3) 0.002(3) 0.002(3) Eu1 0.01644(18) 0.01110(18) 0.01719(18) 0.00012(16) 0.00135(12) -0.00037(16) N1 0.056(5) 0.054(5) 0.024(2) 0.004(2) 0.004(3) 0.000(4) O1 0.021(3) 0.020(3) 0.054(4) 0.002(3) 0.007(2) 0.002(2) O2 0.019(3) 0.019(3) 0.059(4) 0.002(3) 0.004(3) 0.001(2) O3 0.027(3) 0.013(3) 0.028(3) -0.005(2) 0.004(2) 0.002(2) O4 0.016(2) 0.015(3) 0.028(3) -0.001(2) 0.006(2) 0.004(2) O5 0.030(3) 0.014(3) 0.042(3) -0.001(3) -0.005(2) 0.006(2) O6 0.024(3) 0.021(3) 0.027(3) 0.001(2) -0.002(2) -0.004(2) O7 0.047(3) 0.048(4) 0.019(3) 0.002(2) -0.003(3) -0.015(3) O8 0.024(3) 0.025(3) 0.022(3) 0.004(2) 0.005(2) -0.004(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 O9 N1 1.302(7) . ? O9 Eu1 2.502(5) 4_565 ? O9 Eu1 2.505(5) 3 ? C1 O3 1.245(8) . ? C1 O4 1.253(8) . ? C1 C2 1.509(9) . ? C2 O1 1.412(8) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.351(9) . ? C3 O1 1.358(8) . ? C3 C12 1.417(10) . ? C4 C5 1.420(9) . ? C4 H4 0.9300 . ? C5 C6 1.409(9) . ? C5 C10 1.409(9) . ? C6 C7 1.360(9) . ? C6 H6 0.9300 . ? C7 O2 1.369(8) . ? C7 C8 1.403(10) . ? C8 C9 1.350(10) . ? C8 H8 0.9300 . ? C9 C10 1.420(10) . ? C9 H9 0.9300 . ? C10 C11 1.414(10) . ? C11 C12 1.355(10) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O2 1.422(8) . ? C13 C14 1.524(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O6 1.246(8) . ? C14 O5 1.251(8) . ? Eu1 O5 2.335(5) 1_455 ? Eu1 O7 2.416(5) . ? Eu1 O8 2.442(4) . ? Eu1 O4 2.444(5) 2_545 ? Eu1 O6 2.485(5) 2_645 ? Eu1 O3 2.502(5) . ? Eu1 O9 2.502(5) 4_566 ? Eu1 O9 2.505(5) 3 ? Eu1 O4 2.609(5) . ? N1 O7 1.227(8) . ? O4 Eu1 2.444(5) 2 ? O5 Eu1 2.335(5) 1_655 ? O6 Eu1 2.485(5) 2_655 ? O8 H8A 0.8501 . ? O8 H8B 0.8500 . ? 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 O9 Eu1 125.4(4) . 4_565 ? N1 O9 Eu1 119.9(4) . 3 ? Eu1 O9 Eu1 111.35(17) 4_565 3 ? O3 C1 O4 122.8(6) . . ? O3 C1 C2 115.5(6) . . ? O4 C1 C2 121.6(6) . . ? O1 C2 C1 111.6(6) . . ? O1 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? O1 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C4 C3 O1 125.4(7) . . ? C4 C3 C12 120.6(7) . . ? O1 C3 C12 114.0(6) . . ? C3 C4 C5 120.6(7) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C10 119.0(7) . . ? C6 C5 C4 121.7(7) . . ? C10 C5 C4 119.3(7) . . ? C7 C6 C5 120.9(7) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 O2 125.5(6) . . ? C6 C7 C8 120.3(7) . . ? O2 C7 C8 114.2(6) . . ? C9 C8 C7 120.0(7) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 121.4(7) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C5 C10 C11 118.1(7) . . ? C5 C10 C9 118.3(7) . . ? C11 C10 C9 123.6(7) . . ? C12 C11 C10 121.9(7) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C3 119.4(7) . . ? C11 C12 H12 120.3 . . ? C3 C12 H12 120.3 . . ? O2 C13 C14 110.4(6) . . ? O2 C13 H13A 109.6 . . ? C14 C13 H13A 109.6 . . ? O2 C13 H13B 109.6 . . ? C14 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? O6 C14 O5 126.9(6) . . ? O6 C14 C13 121.0(6) . . ? O5 C14 C13 112.1(6) . . ? O5 Eu1 O7 71.96(19) 1_455 . ? O5 Eu1 O8 72.62(16) 1_455 . ? O7 Eu1 O8 69.50(16) . . ? O5 Eu1 O4 99.50(16) 1_455 2_545 ? O7 Eu1 O4 140.57(17) . 2_545 ? O8 Eu1 O4 71.22(15) . 2_545 ? O5 Eu1 O6 137.11(16) 1_455 2_645 ? O7 Eu1 O6 136.81(17) . 2_645 ? O8 Eu1 O6 139.01(15) . 2_645 ? O4 Eu1 O6 75.47(15) 2_545 2_645 ? O5 Eu1 O3 126.46(17) 1_455 . ? O7 Eu1 O3 68.44(17) . . ? O8 Eu1 O3 122.01(15) . . ? O4 Eu1 O3 133.88(15) 2_545 . ? O6 Eu1 O3 68.39(15) 2_645 . ? O5 Eu1 O9 68.20(16) 1_455 4_566 ? O7 Eu1 O9 126.32(18) . 4_566 ? O8 Eu1 O9 126.81(14) . 4_566 ? O4 Eu1 O9 81.21(15) 2_545 4_566 ? O6 Eu1 O9 68.94(15) 2_645 4_566 ? O3 Eu1 O9 110.04(14) . 4_566 ? O5 Eu1 O9 142.17(16) 1_455 3 ? O7 Eu1 O9 94.54(17) . 3 ? O8 Eu1 O9 69.55(15) . 3 ? O4 Eu1 O9 68.34(15) 2_545 3 ? O6 Eu1 O9 76.45(15) 2_645 3 ? O3 Eu1 O9 75.96(15) . 3 ? O9 Eu1 O9 138.55(10) 4_566 3 ? O5 Eu1 O4 86.92(15) 1_455 . ? O7 Eu1 O4 77.69(16) . . ? O8 Eu1 O4 145.26(15) . . ? O4 Eu1 O4 141.40(6) 2_545 . ? O6 Eu1 O4 74.29(15) 2_645 . ? O3 Eu1 O4 50.79(14) . . ? O9 Eu1 O4 65.86(15) 4_566 . ? O9 Eu1 O4 125.53(14) 3 . ? O5 Eu1 Eu1 66.62(12) 1_455 2 ? O7 Eu1 Eu1 96.74(14) . 2 ? O8 Eu1 Eu1 139.24(11) . 2 ? O4 Eu1 Eu1 115.47(11) 2_545 2 ? O6 Eu1 Eu1 77.20(11) 2_645 2 ? O3 Eu1 Eu1 83.73(10) . 2 ? O9 Eu1 Eu1 34.35(11) 4_566 2 ? O9 Eu1 Eu1 151.20(10) 3 2 ? O4 Eu1 Eu1 33.78(10) . 2 ? O5 Eu1 Eu1 132.84(13) 1_455 2_545 ? O7 Eu1 Eu1 126.57(14) . 2_545 ? O8 Eu1 Eu1 75.74(11) . 2_545 ? O4 Eu1 Eu1 36.41(10) 2_545 2_545 ? O6 Eu1 Eu1 63.27(11) 2_645 2_545 ? O3 Eu1 Eu1 99.87(11) . 2_545 ? O9 Eu1 Eu1 106.90(11) 4_566 2_545 ? O9 Eu1 Eu1 34.31(10) 3 2_545 ? O4 Eu1 Eu1 135.84(10) . 2_545 ? Eu1 Eu1 Eu1 134.973(19) 2 2_545 ? O7 N1 O9 123.0(7) . . ? C3 O1 C2 116.8(5) . . ? C7 O2 C13 118.1(5) . . ? C1 O3 Eu1 95.5(4) . . ? C1 O4 Eu1 152.6(4) . 2 ? C1 O4 Eu1 90.3(4) . . ? Eu1 O4 Eu1 109.81(17) 2 . ? C14 O5 Eu1 136.5(5) . 1_655 ? C14 O6 Eu1 131.2(4) . 2_655 ? N1 O7 Eu1 155.9(5) . . ? Eu1 O8 H8A 118.2 . . ? Eu1 O8 H8B 118.0 . . ? H8A O8 H8B 115.4 . . ? 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 O8 H8A O3 0.85 2.15 2.890(6) 144.5 3 O8 H8B O2 0.85 2.25 2.923(7) 135.5 1_445 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.961 _refine_diff_density_min -1.138 _refine_diff_density_rms 0.184 # Attachment '5.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 755012' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N O9 Sm' _chemical_formula_sum 'C14 H12 N O9 Sm' _chemical_formula_weight 488.60 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' Sm Sm -0.1638 3.4418 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 14.6870(16) _cell_length_b 7.6577(8) _cell_length_c 12.9674(14) _cell_angle_alpha 90.00 _cell_angle_beta 92.456(2) _cell_angle_gamma 90.00 _cell_volume 1457.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3734 _cell_measurement_theta_min 2.776 _cell_measurement_theta_max 28.128 _exptl_crystal_description flake-like _exptl_crystal_colour grey _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.227 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 948 _exptl_absorpt_coefficient_mu 4.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.446 _exptl_absorpt_correction_T_max 0.520 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7529 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0569 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2851 _reflns_number_gt 2498 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0582P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2851 _refine_ls_number_parameters 226 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0385 _refine_ls_wR_factor_ref 0.0973 _refine_ls_wR_factor_gt 0.0931 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 1.001 _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 0.1660(4) 0.0754(7) 0.3337(4) 0.0213(12) Uani 1 1 d . . . C2 C 0.2644(4) 0.0382(7) 0.3594(5) 0.0236(13) Uani 1 1 d . . . H2A H 0.3016 0.0896 0.3073 0.028 Uiso 1 1 calc R . . H2B H 0.2820 0.0904 0.4254 0.028 Uiso 1 1 calc R . . C3 C 0.3678(4) -0.2038(8) 0.3695(5) 0.0258(14) Uani 1 1 d . . . C4 C 0.3770(5) -0.3856(8) 0.3742(5) 0.0323(15) Uani 1 1 d . . . H4 H 0.3254 -0.4562 0.3745 0.039 Uiso 1 1 calc R . . C5 C 0.4613(4) -0.4586(8) 0.3784(5) 0.0304(15) Uani 1 1 d . . . H5 H 0.4665 -0.5796 0.3804 0.037 Uiso 1 1 calc R . . C6 C 0.5414(4) -0.3563(8) 0.3797(5) 0.0250(13) Uani 1 1 d . . . C7 C 0.5312(4) -0.1717(8) 0.3752(5) 0.0236(13) Uani 1 1 d . . . C8 C 0.4429(4) -0.0995(7) 0.3710(5) 0.0283(14) Uani 1 1 d . . . H8 H 0.4358 0.0211 0.3691 0.034 Uiso 1 1 calc R . . C9 C 0.6104(4) -0.0681(7) 0.3742(5) 0.0269(14) Uani 1 1 d . . . H9 H 0.6049 0.0528 0.3713 0.032 Uiso 1 1 calc R . . C10 C 0.6945(4) -0.1411(8) 0.3774(5) 0.0244(13) Uani 1 1 d . . . C11 C 0.7050(4) -0.3242(8) 0.3870(5) 0.0291(14) Uani 1 1 d . . . H11 H 0.7629 -0.3735 0.3935 0.035 Uiso 1 1 calc R . . C12 C 0.6300(4) -0.4264(8) 0.3865(5) 0.0319(15) Uani 1 1 d . . . H12 H 0.6372 -0.5469 0.3907 0.038 Uiso 1 1 calc R . . C13 C 0.7687(4) 0.1308(8) 0.3705(5) 0.0268(14) Uani 1 1 d . . . H13A H 0.7438 0.1740 0.4337 0.032 Uiso 1 1 calc R . . H13B H 0.7276 0.1646 0.3134 0.032 Uiso 1 1 calc R . . C14 C 0.8610(4) 0.2115(7) 0.3568(4) 0.0169(11) Uani 1 1 d . . . N1 N 1.0420(4) 0.2322(7) 0.5617(4) 0.0386(14) Uani 1 1 d U . . O1 O 0.1497(3) 0.2357(5) 0.3268(3) 0.0300(10) Uani 1 1 d . . . O2 O 0.1089(3) -0.0443(5) 0.3211(3) 0.0263(9) Uani 1 1 d . . . O3 O 0.2797(3) -0.1450(5) 0.3638(4) 0.0327(11) Uani 1 1 d . . . O4 O 0.7748(3) -0.0521(5) 0.3748(4) 0.0324(11) Uani 1 1 d . . . O5 O 0.8688(3) 0.3649(5) 0.3858(3) 0.0234(9) Uani 1 1 d . . . O6 O 0.9236(3) 0.1304(5) 0.3155(3) 0.0197(8) Uani 1 1 d . . . O7 O 1.1425(3) 0.5889(5) 0.3932(3) 0.0239(9) Uani 1 1 d . . . H7C H 1.1409 0.5465 0.4537 0.029 Uiso 1 1 d R . . H7A H 1.1317 0.6953 0.4067 0.029 Uiso 1 1 d R . . O8 O 1.0391(3) 0.3328(6) 0.4882(3) 0.0337(11) Uani 1 1 d U . . O9 O 1.0364(3) 0.2810(5) 0.6559(3) 0.0209(9) Uani 1 1 d U . . Sm1 Sm 1.020498(18) 0.41595(3) 0.30807(2) 0.01522(13) 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 0.023(3) 0.020(3) 0.020(3) -0.005(2) 0.000(2) 0.002(2) C2 0.021(3) 0.017(3) 0.033(3) 0.001(3) 0.003(3) 0.002(2) C3 0.019(3) 0.026(3) 0.033(3) 0.006(3) -0.001(3) 0.001(2) C4 0.027(3) 0.023(3) 0.047(4) 0.003(3) -0.001(3) -0.004(3) C5 0.032(4) 0.018(3) 0.042(4) 0.007(3) 0.001(3) 0.001(3) C6 0.025(3) 0.016(3) 0.034(3) 0.001(3) 0.002(3) -0.001(2) C7 0.023(3) 0.022(3) 0.027(3) 0.002(2) 0.001(3) -0.002(2) C8 0.024(3) 0.019(3) 0.042(4) 0.002(3) -0.001(3) -0.001(2) C9 0.025(3) 0.015(3) 0.041(4) 0.002(3) 0.003(3) 0.000(2) C10 0.020(3) 0.022(3) 0.031(3) -0.001(3) 0.001(3) -0.002(2) C11 0.020(3) 0.024(3) 0.043(4) 0.005(3) 0.003(3) 0.004(3) C12 0.030(4) 0.023(3) 0.043(4) 0.004(3) -0.002(3) 0.004(3) C13 0.025(3) 0.017(3) 0.039(4) -0.003(3) 0.003(3) -0.001(2) C14 0.020(3) 0.020(3) 0.011(2) 0.003(2) 0.000(2) 0.001(2) N1 0.048(4) 0.038(3) 0.030(2) 0.009(2) 0.000(3) -0.001(3) O1 0.030(2) 0.017(2) 0.043(2) -0.004(2) -0.009(2) 0.0050(18) O2 0.027(2) 0.022(2) 0.030(2) -0.0007(18) -0.0026(19) -0.0025(18) O3 0.020(2) 0.017(2) 0.061(3) 0.003(2) -0.001(2) 0.0010(18) O4 0.022(2) 0.018(2) 0.058(3) 0.000(2) 0.006(2) -0.0009(17) O5 0.027(2) 0.015(2) 0.028(2) -0.0039(17) 0.0038(18) -0.0016(17) O6 0.022(2) 0.0161(19) 0.021(2) -0.0001(16) 0.0026(17) 0.0016(16) O7 0.030(2) 0.020(2) 0.022(2) -0.0007(16) 0.0006(18) -0.0004(17) O8 0.040(3) 0.042(3) 0.019(2) 0.0048(17) -0.001(2) -0.005(2) O9 0.030(2) 0.015(2) 0.0173(18) 0.0012(16) -0.0021(17) -0.0020(17) Sm1 0.01888(18) 0.01089(18) 0.01589(18) 0.00037(10) 0.00048(12) -0.00037(10) _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 O2 1.248(7) . ? C1 O1 1.253(6) . ? C1 C2 1.497(8) . ? C2 O3 1.422(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.361(8) . ? C3 O3 1.369(7) . ? C3 C4 1.400(8) . ? C4 C5 1.357(9) . ? C4 H4 0.9300 . ? C5 C6 1.413(9) . ? C5 H5 0.9300 . ? C6 C12 1.408(9) . ? C6 C7 1.422(8) . ? C7 C9 1.409(8) . ? C7 C8 1.409(8) . ? C8 H8 0.9300 . ? C9 C10 1.354(8) . ? C9 H9 0.9300 . ? C10 O4 1.364(7) . ? C10 C11 1.416(8) . ? C11 C12 1.351(9) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 O4 1.405(7) . ? C13 C14 1.508(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O5 1.238(6) . ? C14 O6 1.249(6) . ? N1 O8 1.224(6) . ? N1 O9 1.283(6) . ? O1 Sm1 2.351(4) 1_455 ? O2 Sm1 2.497(4) 2_645 ? O5 Sm1 2.515(4) . ? O6 Sm1 2.460(4) 2_745 ? O6 Sm1 2.613(4) . ? O7 Sm1 2.452(4) . ? O7 H7C 0.8500 . ? O7 H7A 0.8500 . ? O8 Sm1 2.425(4) . ? O9 Sm1 2.503(4) 4_566 ? O9 Sm1 2.517(4) 3_766 ? Sm1 O1 2.351(4) 1_655 ? Sm1 O6 2.460(4) 2_755 ? Sm1 O2 2.497(4) 2_655 ? Sm1 O9 2.503(4) 4_565 ? Sm1 O9 2.517(4) 3_766 ? 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 O2 C1 O1 125.8(6) . . ? O2 C1 C2 121.7(5) . . ? O1 C1 C2 112.4(5) . . ? O3 C2 C1 110.3(5) . . ? O3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? O3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C8 C3 O3 124.8(5) . . ? C8 C3 C4 120.4(6) . . ? O3 C3 C4 114.7(5) . . ? C5 C4 C3 119.8(6) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 122.0(6) . . ? C4 C5 H5 119.0 . . ? C6 C5 H5 119.0 . . ? C12 C6 C5 123.9(6) . . ? C12 C6 C7 118.4(6) . . ? C5 C6 C7 117.7(6) . . ? C9 C7 C8 122.6(5) . . ? C9 C7 C6 118.4(6) . . ? C8 C7 C6 119.1(5) . . ? C3 C8 C7 121.0(5) . . ? C3 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C10 C9 C7 121.3(5) . . ? C10 C9 H9 119.4 . . ? C7 C9 H9 119.4 . . ? C9 C10 O4 125.6(6) . . ? C9 C10 C11 120.5(6) . . ? O4 C10 C11 113.9(5) . . ? C12 C11 C10 119.2(6) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C11 C12 C6 122.1(6) . . ? C11 C12 H12 119.0 . . ? C6 C12 H12 119.0 . . ? O4 C13 C14 110.9(5) . . ? O4 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? O4 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.0 . . ? O5 C14 O6 122.8(5) . . ? O5 C14 C13 115.2(5) . . ? O6 C14 C13 122.0(5) . . ? O8 N1 O9 123.8(6) . . ? C1 O1 Sm1 137.2(4) . 1_455 ? C1 O2 Sm1 131.7(4) . 2_645 ? C3 O3 C2 118.3(5) . . ? C10 O4 C13 116.4(5) . . ? C14 O5 Sm1 95.6(3) . . ? C14 O6 Sm1 152.0(4) . 2_745 ? C14 O6 Sm1 90.7(3) . . ? Sm1 O6 Sm1 109.72(15) 2_745 . ? Sm1 O7 H7C 99.2 . . ? Sm1 O7 H7A 118.1 . . ? H7C O7 H7A 99.4 . . ? N1 O8 Sm1 156.0(4) . . ? N1 O9 Sm1 126.0(3) . 4_566 ? N1 O9 Sm1 118.7(3) . 3_766 ? Sm1 O9 Sm1 111.48(14) 4_566 3_766 ? O1 Sm1 O8 71.89(16) 1_655 . ? O1 Sm1 O7 72.51(14) 1_655 . ? O8 Sm1 O7 70.03(14) . . ? O1 Sm1 O6 99.73(14) 1_655 2_755 ? O8 Sm1 O6 140.88(14) . 2_755 ? O7 Sm1 O6 71.02(13) . 2_755 ? O1 Sm1 O2 136.79(13) 1_655 2_655 ? O8 Sm1 O2 136.78(15) . 2_655 ? O7 Sm1 O2 139.15(12) . 2_655 ? O6 Sm1 O2 75.37(13) 2_755 2_655 ? O1 Sm1 O9 68.02(13) 1_655 4_565 ? O8 Sm1 O9 126.22(13) . 4_565 ? O7 Sm1 O9 126.11(13) . 4_565 ? O6 Sm1 O9 81.01(13) 2_755 4_565 ? O2 Sm1 O9 68.82(13) 2_655 4_565 ? O1 Sm1 O5 126.33(14) 1_655 . ? O8 Sm1 O5 68.79(14) . . ? O7 Sm1 O5 123.11(13) . . ? O6 Sm1 O5 133.69(13) 2_755 . ? O2 Sm1 O5 68.03(14) 2_655 . ? O9 Sm1 O5 109.67(13) 4_565 . ? O1 Sm1 O9 142.65(13) 1_655 3_766 ? O8 Sm1 O9 95.03(14) . 3_766 ? O7 Sm1 O9 70.15(12) . 3_766 ? O6 Sm1 O9 68.16(12) 2_755 3_766 ? O2 Sm1 O9 76.29(12) 2_655 3_766 ? O9 Sm1 O9 138.15(8) 4_565 3_766 ? O5 Sm1 O9 76.23(13) . 3_766 ? O1 Sm1 O6 86.75(13) 1_655 . ? O8 Sm1 O6 77.51(14) . . ? O7 Sm1 O6 145.49(12) . . ? O6 Sm1 O6 141.27(6) 2_755 . ? O2 Sm1 O6 74.14(12) 2_655 . ? O9 Sm1 O6 66.05(13) 4_565 . ? O5 Sm1 O6 50.37(12) . . ? O9 Sm1 O6 125.40(13) 3_766 . ? 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 O7 H7C O5 0.85 2.20 2.900(6) 139.5 3_766 O7 H7C O8 0.85 2.27 2.799(6) 120.0 . O7 H7A O2 0.85 2.30 2.995(6) 139.2 1_665 O7 H7A N1 0.85 2.66 3.114(7) 114.9 3_766 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.446 _refine_diff_density_min -0.960 _refine_diff_density_rms 0.185 # Attachment '6.cif' data_90107am _database_code_depnum_ccdc_archive 'CCDC 755656' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 Cd O7' _chemical_formula_sum 'C16 H14 Cd O7' _chemical_formula_weight 430.67 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' Cd Cd -0.8075 1.2024 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1081(11) _cell_length_b 7.8775(15) _cell_length_c 15.452(3) _cell_angle_alpha 77.892(3) _cell_angle_beta 87.069(4) _cell_angle_gamma 88.392(4) _cell_volume 725.9(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1088 _cell_measurement_theta_min 2.645 _cell_measurement_theta_max 23.496 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.970 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 1.543 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.757 _exptl_absorpt_correction_T_max 0.781 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3649 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0922 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2508 _reflns_number_gt 1971 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0090P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2508 _refine_ls_number_parameters 217 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.003 _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 0.1455(10) 0.6491(8) 0.1201(4) 0.0388(16) Uani 1 1 d U . . C2 C -0.0060(10) 0.5118(8) 0.1658(4) 0.057(2) Uani 1 1 d . . . H2A H -0.0333 0.4347 0.1263 0.068 Uiso 1 1 calc R . . H2B H 0.0626 0.4439 0.2174 0.068 Uiso 1 1 calc R . . C3 C -0.2728(10) 0.5571(8) 0.2806(4) 0.0396(16) Uani 1 1 d . . . C4 C -0.4641(10) 0.6395(9) 0.2989(4) 0.053(2) Uani 1 1 d . . . H4 H -0.5361 0.7119 0.2532 0.063 Uiso 1 1 calc R . . C5 C -0.5507(10) 0.6160(9) 0.3842(4) 0.0502(19) Uani 1 1 d . . . H5 H -0.6820 0.6725 0.3948 0.060 Uiso 1 1 calc R . . C6 C -0.4518(9) 0.5133(7) 0.4538(4) 0.0336(15) Uani 1 1 d . . . C7 C -0.2573(10) 0.4373(9) 0.4344(4) 0.057(2) Uani 1 1 d . . . H7 H -0.1816 0.3702 0.4806 0.068 Uiso 1 1 calc R . . C8 C -0.1675(11) 0.4554(9) 0.3489(4) 0.054(2) Uani 1 1 d . . . H8 H -0.0365 0.3987 0.3382 0.065 Uiso 1 1 calc R . . C9 C 0.7196(9) 1.0967(7) 0.1171(4) 0.0303(14) Uani 1 1 d . . . C10 C 0.5975(9) 1.1519(8) 0.1941(3) 0.0364(16) Uani 1 1 d . . . H10A H 0.6750 1.1088 0.2478 0.044 Uiso 1 1 calc R . . H10B H 0.5915 1.2777 0.1840 0.044 Uiso 1 1 calc R . . C11 C 0.2777(9) 1.0710(7) 0.2890(3) 0.0258(12) Uani 1 1 d U . . C12 C 0.0947(8) 0.9709(7) 0.3051(3) 0.0300(14) Uani 1 1 d . . . H12 H 0.0437 0.9204 0.2608 0.036 Uiso 1 1 calc R . . C13 C -0.0140(9) 0.9451(7) 0.3873(3) 0.0303(13) Uani 1 1 d U . . H13 H -0.1393 0.8780 0.3971 0.036 Uiso 1 1 calc R . . C14 C 0.0571(9) 1.0153(7) 0.4552(3) 0.0276(13) Uani 1 1 d U . . C15 C 0.2429(9) 1.1158(8) 0.4366(4) 0.0403(16) Uani 1 1 d . . . H15 H 0.2965 1.1655 0.4806 0.048 Uiso 1 1 calc R . . C16 C 0.3511(10) 1.1439(8) 0.3537(3) 0.0395(16) Uani 1 1 d U . . H16 H 0.4744 1.2131 0.3426 0.047 Uiso 1 1 calc R . . Cd1 Cd 0.24138(7) 1.04402(6) 0.05942(3) 0.03863(18) Uani 1 1 d U . . O1 O -0.2093(7) 0.5817(6) 0.1929(3) 0.0560(13) Uani 1 1 d . . . O2 O 0.3802(6) 1.0866(5) 0.2051(2) 0.0341(9) Uani 1 1 d U . . O3 O 0.1030(7) 0.8007(6) 0.1261(3) 0.0654(15) Uani 1 1 d . . . O4 O 0.3086(7) 0.5966(6) 0.0811(3) 0.0585(14) Uani 1 1 d U . . O5 O 0.9140(6) 1.1443(5) 0.1041(2) 0.0416(11) Uani 1 1 d . . . O6 O 0.6192(6) 1.0131(5) 0.0705(2) 0.0369(10) Uani 1 1 d . . . O7 O 0.3031(7) 1.3199(5) 0.0052(3) 0.0495(12) Uani 1 1 d . . . H7B H 0.4419 1.3159 0.0079 0.059 Uiso 1 1 d R . . H7A H 0.2750 1.3919 0.0385 0.059 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 0.041(4) 0.042(4) 0.037(4) -0.020(3) 0.012(3) -0.007(3) C2 0.049(5) 0.050(5) 0.063(5) -0.004(4) 0.037(4) 0.006(4) C3 0.031(4) 0.036(4) 0.051(4) -0.011(3) 0.013(3) -0.006(3) C4 0.047(5) 0.056(5) 0.044(4) 0.010(4) 0.008(3) 0.015(4) C5 0.041(4) 0.058(5) 0.045(4) -0.002(4) 0.009(3) 0.024(4) C6 0.032(4) 0.032(4) 0.039(4) -0.014(3) 0.000(3) 0.000(3) C7 0.049(5) 0.081(6) 0.040(4) -0.013(4) -0.006(3) 0.032(4) C8 0.036(4) 0.072(5) 0.054(5) -0.017(4) 0.006(3) 0.024(4) C9 0.028(4) 0.033(4) 0.026(3) 0.000(3) 0.004(3) 0.000(3) C10 0.027(3) 0.056(4) 0.028(3) -0.016(3) 0.013(3) -0.007(3) C11 0.024(3) 0.031(3) 0.020(3) -0.005(2) 0.007(2) 0.007(3) C12 0.026(3) 0.038(4) 0.027(3) -0.010(3) 0.002(3) 0.003(3) C13 0.022(3) 0.038(4) 0.028(3) -0.003(3) 0.004(2) 0.000(3) C14 0.028(3) 0.027(3) 0.027(3) -0.005(2) 0.008(2) 0.005(3) C15 0.047(4) 0.050(4) 0.028(3) -0.019(3) 0.009(3) -0.012(3) C16 0.041(4) 0.048(4) 0.031(3) -0.014(3) 0.014(3) -0.014(3) Cd1 0.0268(3) 0.0447(3) 0.0518(3) -0.0307(2) 0.0200(2) -0.0115(2) O1 0.047(3) 0.064(3) 0.046(3) 0.006(2) 0.024(2) 0.008(2) O2 0.023(2) 0.047(3) 0.0311(19) -0.0103(19) 0.0152(15) -0.0025(19) O3 0.066(3) 0.036(3) 0.099(4) -0.033(3) 0.040(3) -0.016(3) O4 0.042(3) 0.052(3) 0.086(3) -0.031(3) 0.032(2) -0.012(2) O5 0.022(2) 0.049(3) 0.054(3) -0.014(2) 0.017(2) -0.005(2) O6 0.024(2) 0.050(3) 0.042(2) -0.025(2) 0.0132(19) -0.008(2) O7 0.039(3) 0.050(3) 0.062(3) -0.024(2) 0.024(2) -0.006(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 1.244(6) . ? C1 O3 1.236(7) . ? C1 C2 1.481(8) . ? C2 O1 1.423(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.362(8) . ? C3 C4 1.366(8) . ? C3 O1 1.367(6) . ? C4 C5 1.373(7) . ? C4 H4 0.9300 . ? C5 C6 1.360(8) . ? C5 H5 0.9300 . ? C6 C7 1.364(8) . ? C6 C6 1.490(10) 2_466 ? C7 C8 1.384(7) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 O5 1.249(6) . ? C9 O6 1.263(7) . ? C9 C10 1.507(7) . ? C10 O2 1.426(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C16 1.353(7) . ? C11 C12 1.368(7) . ? C11 O2 1.395(5) . ? C12 C13 1.382(6) . ? C12 H12 0.9300 . ? C13 C14 1.378(7) . ? C13 H13 0.9300 . ? C14 C15 1.385(7) . ? C14 C14 1.495(9) 2_576 ? C15 C16 1.389(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? Cd1 O3 2.150(4) . ? Cd1 O7 2.195(4) . ? Cd1 O5 2.258(4) 1_455 ? Cd1 O6 2.268(3) 2_675 ? Cd1 O6 2.325(4) . ? Cd1 O2 2.534(4) . ? O5 Cd1 2.258(4) 1_655 ? O6 Cd1 2.268(3) 2_675 ? O7 H7B 0.8500 . ? O7 H7A 0.8500 . ? 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 O3 126.7(6) . . ? O4 C1 C2 115.0(6) . . ? O3 C1 C2 118.3(5) . . ? O1 C2 C1 112.1(5) . . ? O1 C2 H2A 109.2 . . ? C1 C2 H2A 109.2 . . ? O1 C2 H2B 109.2 . . ? C1 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C8 C3 C4 118.7(6) . . ? C8 C3 O1 126.0(6) . . ? C4 C3 O1 115.2(6) . . ? C3 C4 C5 120.4(6) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C6 C5 C4 122.5(6) . . ? C6 C5 H5 118.7 . . ? C4 C5 H5 118.7 . . ? C5 C6 C7 116.0(5) . . ? C5 C6 C6 122.2(7) . 2_466 ? C7 C6 C6 121.8(7) . 2_466 ? C6 C7 C8 123.0(6) . . ? C6 C7 H7 118.5 . . ? C8 C7 H7 118.5 . . ? C3 C8 C7 119.4(6) . . ? C3 C8 H8 120.3 . . ? C7 C8 H8 120.3 . . ? O5 C9 O6 125.9(5) . . ? O5 C9 C10 115.2(5) . . ? O6 C9 C10 118.9(5) . . ? O2 C10 C9 110.7(5) . . ? O2 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? O2 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? C16 C11 C12 119.9(5) . . ? C16 C11 O2 124.3(5) . . ? C12 C11 O2 115.9(5) . . ? C11 C12 C13 119.7(5) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 122.2(5) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 116.5(5) . . ? C13 C14 C14 122.4(6) . 2_576 ? C15 C14 C14 121.1(6) . 2_576 ? C14 C15 C16 121.5(5) . . ? C14 C15 H15 119.3 . . ? C16 C15 H15 119.3 . . ? C11 C16 C15 120.3(5) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? O3 Cd1 O7 164.92(14) . . ? O3 Cd1 O5 81.30(15) . 1_455 ? O7 Cd1 O5 83.68(14) . 1_455 ? O3 Cd1 O6 103.26(15) . 2_675 ? O7 Cd1 O6 88.16(14) . 2_675 ? O5 Cd1 O6 134.10(15) 1_455 2_675 ? O3 Cd1 O6 106.66(17) . . ? O7 Cd1 O6 85.94(15) . . ? O5 Cd1 O6 150.45(14) 1_455 . ? O6 Cd1 O6 72.88(16) 2_675 . ? O3 Cd1 O2 89.80(16) . . ? O7 Cd1 O2 88.00(14) . . ? O5 Cd1 O2 86.55(13) 1_455 . ? O6 Cd1 O2 138.33(13) 2_675 . ? O6 Cd1 O2 65.46(11) . . ? C3 O1 C2 120.5(5) . . ? C11 O2 C10 116.5(4) . . ? C11 O2 Cd1 131.8(3) . . ? C10 O2 Cd1 111.4(3) . . ? C1 O3 Cd1 132.2(4) . . ? C9 O5 Cd1 139.0(4) . 1_655 ? C9 O6 Cd1 123.7(3) . 2_675 ? C9 O6 Cd1 120.6(3) . . ? Cd1 O6 Cd1 107.12(16) 2_675 . ? Cd1 O7 H7B 97.9 . . ? Cd1 O7 H7A 118.3 . . ? H7B O7 H7A 98.4 . . ? 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 O1 -167.7(5) . . . . ? O3 C1 C2 O1 14.2(9) . . . . ? C8 C3 C4 C5 -1.7(10) . . . . ? O1 C3 C4 C5 176.2(6) . . . . ? C3 C4 C5 C6 0.7(11) . . . . ? C4 C5 C6 C7 1.5(10) . . . . ? C4 C5 C6 C6 -179.3(7) . . . 2_466 ? C5 C6 C7 C8 -2.8(10) . . . . ? C6 C6 C7 C8 178.0(7) 2_466 . . . ? C4 C3 C8 C7 0.5(10) . . . . ? O1 C3 C8 C7 -177.1(6) . . . . ? C6 C7 C8 C3 1.9(11) . . . . ? O5 C9 C10 O2 -178.1(5) . . . . ? O6 C9 C10 O2 3.9(8) . . . . ? C16 C11 C12 C13 0.1(9) . . . . ? O2 C11 C12 C13 178.4(5) . . . . ? C11 C12 C13 C14 -0.9(9) . . . . ? C12 C13 C14 C15 0.8(8) . . . . ? C12 C13 C14 C14 -178.7(6) . . . 2_576 ? C13 C14 C15 C16 0.1(9) . . . . ? C14 C14 C15 C16 179.5(6) 2_576 . . . ? C12 C11 C16 C15 0.8(9) . . . . ? O2 C11 C16 C15 -177.5(5) . . . . ? C14 C15 C16 C11 -0.9(10) . . . . ? C8 C3 O1 C2 -6.3(10) . . . . ? C4 C3 O1 C2 176.0(6) . . . . ? C1 C2 O1 C3 -117.3(6) . . . . ? C16 C11 O2 C10 13.6(8) . . . . ? C12 C11 O2 C10 -164.7(5) . . . . ? C16 C11 O2 Cd1 -160.3(4) . . . . ? C12 C11 O2 Cd1 21.4(7) . . . . ? C9 C10 O2 C11 157.2(4) . . . . ? C9 C10 O2 Cd1 -27.7(6) . . . . ? O3 Cd1 O2 C11 -48.1(4) . . . . ? O7 Cd1 O2 C11 117.0(4) . . . . ? O5 Cd1 O2 C11 33.2(4) 1_455 . . . ? O6 Cd1 O2 C11 -158.0(4) 2_675 . . . ? O6 Cd1 O2 C11 -156.6(5) . . . . ? O3 Cd1 O2 C10 137.8(4) . . . . ? O7 Cd1 O2 C10 -57.2(4) . . . . ? O5 Cd1 O2 C10 -140.9(4) 1_455 . . . ? O6 Cd1 O2 C10 27.8(4) 2_675 . . . ? O6 Cd1 O2 C10 29.3(3) . . . . ? O4 C1 O3 Cd1 11.9(12) . . . . ? C2 C1 O3 Cd1 -170.3(5) . . . . ? O7 Cd1 O3 C1 163.9(6) . . . . ? O5 Cd1 O3 C1 158.9(7) 1_455 . . . ? O6 Cd1 O3 C1 25.5(7) 2_675 . . . ? O6 Cd1 O3 C1 -50.3(7) . . . . ? O2 Cd1 O3 C1 -114.6(7) . . . . ? O6 C9 O5 Cd1 -38.1(9) . . . 1_655 ? C10 C9 O5 Cd1 144.1(4) . . . 1_655 ? O5 C9 O6 Cd1 -7.6(8) . . . 2_675 ? C10 C9 O6 Cd1 170.2(4) . . . 2_675 ? O5 C9 O6 Cd1 -151.2(5) . . . . ? C10 C9 O6 Cd1 26.5(7) . . . . ? O3 Cd1 O6 C9 -112.0(4) . . . . ? O7 Cd1 O6 C9 59.6(4) . . . . ? O5 Cd1 O6 C9 -10.0(6) 1_455 . . . ? O6 Cd1 O6 C9 148.9(5) 2_675 . . . ? O2 Cd1 O6 C9 -30.1(4) . . . . ? O3 Cd1 O6 Cd1 99.11(19) . . . 2_675 ? O7 Cd1 O6 Cd1 -89.33(17) . . . 2_675 ? O5 Cd1 O6 Cd1 -158.9(2) 1_455 . . 2_675 ? O6 Cd1 O6 Cd1 0.0 2_675 . . 2_675 ? O2 Cd1 O6 Cd1 -179.0(2) . . . 2_675 ? 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 O7 H7B O4 0.85 2.03 2.689(5) 133.3 2_675 O7 H7A O4 0.85 1.89 2.684(6) 156.0 1_565 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.926 _refine_diff_density_min -0.650 _refine_diff_density_rms 0.110 # Attachment '7.cif' data_7 _database_code_depnum_ccdc_archive 'CCDC 755657' #TrackingRef '7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 Co O10' _chemical_formula_sum 'C16 H20 Co O10' _chemical_formula_weight 431.25 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' Co Co 0.3494 0.9721 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9236(10) _cell_length_b 5.7501(11) _cell_length_c 15.143(3) _cell_angle_alpha 88.367(3) _cell_angle_beta 83.723(3) _cell_angle_gamma 83.308(3) _cell_volume 423.19(14) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1055 _cell_measurement_theta_min 2.707 _cell_measurement_theta_max 27.131 _exptl_crystal_description prism _exptl_crystal_colour purple _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.692 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 223 _exptl_absorpt_coefficient_mu 1.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.807 _exptl_absorpt_correction_T_max 0.843 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2119 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1462 _reflns_number_gt 1329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0723P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1462 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0467 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1129 _refine_ls_wR_factor_gt 0.1101 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.000 _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 0.0927(6) 0.7692(6) 0.1611(2) 0.0234(7) Uani 1 1 d . . . C2 C 0.2499(7) 0.7925(6) 0.2404(2) 0.0270(7) Uani 1 1 d . . . H2A H 0.1229 0.8128 0.2969 0.032 Uiso 1 1 d R . . H2B H 0.3457 0.9355 0.2354 0.032 Uiso 1 1 d R . . C3 C 0.5915(7) 0.5787(6) 0.3196(2) 0.0257(7) Uani 1 1 d . . . C4 C 0.5764(8) 0.7500(7) 0.3817(2) 0.0377(9) Uani 1 1 d . . . H4 H 0.4587 0.8876 0.3771 0.045 Uiso 1 1 calc R . . C5 C 0.7381(8) 0.7165(7) 0.4516(2) 0.0367(9) Uani 1 1 d . . . H5 H 0.7262 0.8344 0.4931 0.044 Uiso 1 1 calc R . . C6 C 0.9151(7) 0.5167(6) 0.4622(2) 0.0267(8) Uani 1 1 d . . . C7 C 0.9261(8) 0.3482(6) 0.3975(3) 0.0434(10) Uani 1 1 d . . . H7 H 1.0446 0.2109 0.4014 0.052 Uiso 1 1 calc R . . C8 C 0.7685(8) 0.3774(6) 0.3281(3) 0.0420(10) Uani 1 1 d . . . H8 H 0.7810 0.2602 0.2863 0.050 Uiso 1 1 calc R . . Co1 Co 0.0000 0.5000 0.0000 0.0208(2) Uani 1 2 d S . . O1 O 0.2874(4) 0.6628(4) -0.08666(14) 0.0286(5) Uani 1 1 d . . . H1B H 0.4553 0.6072 -0.0874 0.034 Uiso 1 1 d R . . H1A H 0.2365 0.7261 -0.1345 0.034 Uiso 1 1 d R . . O2 O -0.2691(5) 0.8031(4) -0.00032(15) 0.0300(6) Uani 1 1 d . . . H2E H -0.2124 0.8693 0.0425 0.036 Uiso 1 1 d R . . H2C H -0.4347 0.8000 0.0221 0.036 Uiso 1 1 d R . . O3 O 0.1840(4) 0.6137(4) 0.10603(14) 0.0284(5) Uani 1 1 d . . . O4 O -0.1172(4) 0.9132(4) 0.15724(15) 0.0305(6) Uani 1 1 d . . . O5 O 0.4433(5) 0.5906(4) 0.24789(15) 0.0297(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 0.0246(17) 0.0278(17) 0.0186(16) 0.0033(13) -0.0065(13) -0.0038(14) C2 0.0257(18) 0.0320(18) 0.0234(17) -0.0068(14) -0.0087(14) 0.0033(14) C3 0.0241(17) 0.0362(19) 0.0177(16) 0.0000(14) -0.0071(13) -0.0022(14) C4 0.039(2) 0.041(2) 0.032(2) -0.0096(16) -0.0192(17) 0.0146(17) C5 0.040(2) 0.043(2) 0.0281(19) -0.0159(16) -0.0180(16) 0.0093(17) C6 0.0289(19) 0.0325(19) 0.0196(17) 0.0004(14) -0.0091(14) -0.0019(14) C7 0.058(3) 0.033(2) 0.041(2) -0.0091(17) -0.030(2) 0.0149(18) C8 0.059(3) 0.035(2) 0.034(2) -0.0136(16) -0.0266(19) 0.0087(18) Co1 0.0199(4) 0.0223(4) 0.0204(4) -0.0030(2) -0.0071(2) 0.0024(2) O1 0.0236(12) 0.0327(13) 0.0281(13) 0.0025(10) -0.0056(10) 0.0044(10) O2 0.0227(12) 0.0293(13) 0.0379(14) -0.0056(10) -0.0100(10) 0.0053(9) O3 0.0257(12) 0.0353(13) 0.0241(12) -0.0095(10) -0.0104(10) 0.0061(10) O4 0.0299(13) 0.0319(13) 0.0290(13) -0.0021(10) -0.0102(11) 0.0068(10) O5 0.0319(13) 0.0345(13) 0.0234(12) -0.0085(10) -0.0150(10) 0.0071(10) _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 1.250(4) . ? C1 O4 1.252(4) . ? C1 C2 1.516(4) . ? C2 O5 1.423(4) . ? C2 H2A 1.0036 . ? C2 H2B 0.9914 . ? C3 O5 1.368(4) . ? C3 C4 1.372(5) . ? C3 C8 1.377(5) . ? C4 C5 1.388(5) . ? C4 H4 0.9300 . ? C5 C6 1.376(5) . ? C5 H5 0.9300 . ? C6 C7 1.390(5) . ? C6 C6 1.485(6) 2_766 ? C7 C8 1.368(5) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? Co1 O2 2.063(2) 2_565 ? Co1 O2 2.063(2) . ? Co1 O3 2.084(2) 2_565 ? Co1 O3 2.084(2) . ? Co1 O1 2.105(2) . ? Co1 O1 2.105(2) 2_565 ? O1 H1B 0.8500 . ? O1 H1A 0.8501 . ? O2 H2E 0.8500 . ? O2 H2C 0.8500 . ? 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 O4 126.6(3) . . ? O3 C1 C2 118.1(3) . . ? O4 C1 C2 115.3(3) . . ? O5 C2 C1 109.6(3) . . ? O5 C2 H2A 109.8 . . ? C1 C2 H2A 111.5 . . ? O5 C2 H2B 110.0 . . ? C1 C2 H2B 111.4 . . ? H2A C2 H2B 104.5 . . ? O5 C3 C4 125.1(3) . . ? O5 C3 C8 116.0(3) . . ? C4 C3 C8 118.9(3) . . ? C3 C4 C5 119.5(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 123.0(3) . . ? C6 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? C5 C6 C7 115.8(3) . . ? C5 C6 C6 122.1(4) . 2_766 ? C7 C6 C6 122.1(4) . 2_766 ? C8 C7 C6 122.2(3) . . ? C8 C7 H7 118.9 . . ? C6 C7 H7 118.9 . . ? C7 C8 C3 120.6(3) . . ? C7 C8 H8 119.7 . . ? C3 C8 H8 119.7 . . ? O2 Co1 O2 180.0 2_565 . ? O2 Co1 O3 91.86(9) 2_565 2_565 ? O2 Co1 O3 88.14(9) . 2_565 ? O2 Co1 O3 88.14(9) 2_565 . ? O2 Co1 O3 91.86(9) . . ? O3 Co1 O3 180.00(7) 2_565 . ? O2 Co1 O1 90.39(9) 2_565 . ? O2 Co1 O1 89.61(9) . . ? O3 Co1 O1 91.69(9) 2_565 . ? O3 Co1 O1 88.31(9) . . ? O2 Co1 O1 89.61(9) 2_565 2_565 ? O2 Co1 O1 90.39(9) . 2_565 ? O3 Co1 O1 88.31(9) 2_565 2_565 ? O3 Co1 O1 91.69(9) . 2_565 ? O1 Co1 O1 180.0 . 2_565 ? Co1 O1 H1B 117.1 . . ? Co1 O1 H1A 118.7 . . ? H1B O1 H1A 117.1 . . ? Co1 O2 H2E 97.4 . . ? Co1 O2 H2C 119.1 . . ? H2E O2 H2C 97.6 . . ? C1 O3 Co1 128.9(2) . . ? C3 O5 C2 116.7(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 O3 C1 C2 O5 -13.9(4) . . . . ? O4 C1 C2 O5 167.0(3) . . . . ? O5 C3 C4 C5 180.0(3) . . . . ? C8 C3 C4 C5 -0.2(6) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C4 C5 C6 C7 0.8(6) . . . . ? C4 C5 C6 C6 -179.5(4) . . . 2_766 ? C5 C6 C7 C8 -0.8(6) . . . . ? C6 C6 C7 C8 179.5(4) 2_766 . . . ? C6 C7 C8 C3 0.3(6) . . . . ? O5 C3 C8 C7 180.0(3) . . . . ? C4 C3 C8 C7 0.2(6) . . . . ? O4 C1 O3 Co1 -10.2(5) . . . . ? C2 C1 O3 Co1 170.8(2) . . . . ? O2 Co1 O3 C1 -160.7(3) 2_565 . . . ? O2 Co1 O3 C1 19.3(3) . . . . ? O3 Co1 O3 C1 -90(100) 2_565 . . . ? O1 Co1 O3 C1 108.8(3) . . . . ? O1 Co1 O3 C1 -71.2(3) 2_565 . . . ? C4 C3 O5 C2 -3.1(5) . . . . ? C8 C3 O5 C2 177.1(3) . . . . ? C1 C2 O5 C3 -176.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B O3 0.85 2.06 2.878(3) 162.1 2_665 O1 H1B O2 0.85 2.38 2.868(3) 116.7 1_655 O1 H1A O4 0.85 2.12 2.713(3) 126.7 2_575 O2 H2E O4 0.85 1.88 2.691(3) 159.2 . O2 H2E O3 0.85 2.56 2.979(3) 111.5 . O2 H2C O1 0.85 2.45 2.868(3) 110.7 1_455 O2 H2C O2 0.85 2.59 3.015(4) 111.8 2_475 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.399 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.082 # Attachment '8.cif' data_81222am _database_code_depnum_ccdc_archive 'CCDC 755658' #TrackingRef '8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H20 Ni O10' _chemical_formula_sum 'C16 H20 Ni O10' _chemical_formula_weight 431.03 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' Ni Ni 0.3393 1.1124 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9002(16) _cell_length_b 5.7233(18) _cell_length_c 15.147(5) _cell_angle_alpha 88.524(7) _cell_angle_beta 83.761(6) _cell_angle_gamma 83.354(6) _cell_volume 419.4(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 790 _cell_measurement_theta_min 2.706 _cell_measurement_theta_max 26.557 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.707 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 224 _exptl_absorpt_coefficient_mu 1.214 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.784 _exptl_absorpt_correction_T_max 0.823 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2098 _diffrn_reflns_av_R_equivalents 0.0515 _diffrn_reflns_av_sigmaI/netI 0.0741 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1447 _reflns_number_gt 1274 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0554P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1447 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0468 _refine_ls_wR_factor_ref 0.1125 _refine_ls_wR_factor_gt 0.1092 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.000 _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 0.0910(7) 0.2680(6) 0.1596(2) 0.0204(8) Uani 1 1 d . . . C2 C 0.2493(8) 0.2923(7) 0.2392(3) 0.0264(9) Uani 1 1 d . . . H2A H 0.3443 0.4322 0.2321 0.032 Uiso 1 1 calc R . . H2B H 0.1218 0.3079 0.2929 0.032 Uiso 1 1 calc R . . C3 C 0.5913(8) 0.0766(7) 0.3188(2) 0.0245(9) Uani 1 1 d . . . C4 C 0.5779(9) 0.2501(7) 0.3809(3) 0.0346(11) Uani 1 1 d . . . H4 H 0.4622 0.3893 0.3756 0.042 Uiso 1 1 calc R . . C5 C 0.7366(9) 0.2172(7) 0.4512(3) 0.0360(11) Uani 1 1 d . . . H5 H 0.7213 0.3349 0.4933 0.043 Uiso 1 1 calc R . . C6 C 0.9171(8) 0.0165(7) 0.4616(2) 0.0258(9) Uani 1 1 d . . . C7 C 0.9262(10) -0.1515(7) 0.3974(3) 0.0425(13) Uani 1 1 d . . . H7 H 1.0441 -0.2899 0.4017 0.051 Uiso 1 1 calc R . . C8 C 0.7686(10) -0.1236(7) 0.3273(3) 0.0410(12) Uani 1 1 d . . . H8 H 0.7828 -0.2415 0.2853 0.049 Uiso 1 1 calc R . . Ni1 Ni 0.0000 0.0000 0.0000 0.0194(3) Uani 1 2 d S . . O1 O 0.1807(5) 0.1094(4) 0.10518(17) 0.0265(6) Uani 1 1 d . . . O2 O -0.1203(5) 0.4128(4) 0.15629(17) 0.0273(7) Uani 1 1 d . . . O3 O 0.4443(5) 0.0901(4) 0.24623(17) 0.0281(7) Uani 1 1 d . . . O4 O -0.2852(5) -0.1644(4) 0.08422(17) 0.0264(6) Uani 1 1 d . . . H4C H -0.2290 -0.1298 0.1329 0.032 Uiso 1 1 d R . . H4B H -0.4494 -0.0974 0.0940 0.032 Uiso 1 1 d R . . O5 O -0.2643(5) 0.2995(4) -0.00203(17) 0.0275(7) Uani 1 1 d . . . H5C H -0.2085 0.3656 0.0412 0.033 Uiso 1 1 d R . . H5A H -0.4312 0.2964 0.0198 0.033 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 0.021(2) 0.020(2) 0.020(2) 0.0016(16) -0.0046(16) -0.0027(16) C2 0.024(2) 0.029(2) 0.026(2) -0.0091(17) -0.0094(17) 0.0050(17) C3 0.022(2) 0.031(2) 0.021(2) -0.0019(17) -0.0074(16) -0.0012(17) C4 0.035(2) 0.033(2) 0.036(2) -0.0097(19) -0.019(2) 0.0114(19) C5 0.044(3) 0.034(2) 0.030(2) -0.0153(19) -0.018(2) 0.011(2) C6 0.030(2) 0.028(2) 0.021(2) 0.0011(16) -0.0093(18) -0.0021(17) C7 0.055(3) 0.031(2) 0.042(3) -0.010(2) -0.030(2) 0.016(2) C8 0.058(3) 0.031(2) 0.035(3) -0.015(2) -0.026(2) 0.010(2) Ni1 0.0187(4) 0.0188(4) 0.0211(4) -0.0039(3) -0.0080(3) 0.0025(3) O1 0.0261(15) 0.0276(15) 0.0261(15) -0.0099(12) -0.0115(12) 0.0055(11) O2 0.0272(15) 0.0263(15) 0.0280(16) -0.0025(12) -0.0105(12) 0.0057(12) O3 0.0310(16) 0.0298(15) 0.0243(15) -0.0089(12) -0.0151(12) 0.0069(12) O4 0.0216(14) 0.0303(15) 0.0272(15) -0.0024(12) -0.0058(12) 0.0008(11) O5 0.0231(15) 0.0258(15) 0.0342(16) -0.0060(12) -0.0109(12) 0.0028(11) _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 O1 1.251(4) . ? C1 O2 1.254(4) . ? C1 C2 1.520(5) . ? C2 O3 1.422(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C8 1.368(5) . ? C3 O3 1.373(4) . ? C3 C4 1.377(5) . ? C4 C5 1.382(5) . ? C4 H4 0.9300 . ? C5 C6 1.383(5) . ? C5 H5 0.9300 . ? C6 C7 1.379(6) . ? C6 C6 1.485(7) 2_756 ? C7 C8 1.376(6) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? Ni1 O5 2.027(2) 2 ? Ni1 O5 2.027(2) . ? Ni1 O1 2.050(2) . ? Ni1 O1 2.050(2) 2 ? Ni1 O4 2.079(3) . ? Ni1 O4 2.079(3) 2 ? O4 H4C 0.8500 . ? O4 H4B 0.8500 . ? O5 H5C 0.8499 . ? O5 H5A 0.8500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 126.9(3) . . ? O1 C1 C2 118.1(3) . . ? O2 C1 C2 115.0(3) . . ? O3 C2 C1 109.4(3) . . ? O3 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O3 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C8 C3 O3 116.4(3) . . ? C8 C3 C4 118.6(4) . . ? O3 C3 C4 125.0(3) . . ? C3 C4 C5 120.0(4) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 122.7(4) . . ? C4 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C7 C6 C5 115.4(4) . . ? C7 C6 C6 122.8(4) . 2_756 ? C5 C6 C6 121.8(4) . 2_756 ? C8 C7 C6 122.9(4) . . ? C8 C7 H7 118.5 . . ? C6 C7 H7 118.5 . . ? C3 C8 C7 120.4(4) . . ? C3 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? O5 Ni1 O5 180.00(12) 2 . ? O5 Ni1 O1 87.27(10) 2 . ? O5 Ni1 O1 92.73(10) . . ? O5 Ni1 O1 92.73(10) 2 2 ? O5 Ni1 O1 87.27(10) . 2 ? O1 Ni1 O1 180.00(8) . 2 ? O5 Ni1 O4 88.70(11) 2 . ? O5 Ni1 O4 91.30(11) . . ? O1 Ni1 O4 91.73(11) . . ? O1 Ni1 O4 88.27(11) 2 . ? O5 Ni1 O4 91.30(11) 2 2 ? O5 Ni1 O4 88.70(11) . 2 ? O1 Ni1 O4 88.27(11) . 2 ? O1 Ni1 O4 91.73(11) 2 2 ? O4 Ni1 O4 180.00(17) . 2 ? C1 O1 Ni1 128.8(2) . . ? C3 O3 C2 116.8(3) . . ? Ni1 O4 H4C 97.3 . . ? Ni1 O4 H4B 118.9 . . ? H4C O4 H4B 97.5 . . ? Ni1 O5 H5C 96.9 . . ? Ni1 O5 H5A 118.8 . . ? H5C O5 H5A 97.6 . . ? 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 O1 C1 C2 O3 -12.6(5) . . . . ? O2 C1 C2 O3 167.2(3) . . . . ? C8 C3 C4 C5 -1.6(7) . . . . ? O3 C3 C4 C5 -179.8(4) . . . . ? C3 C4 C5 C6 1.5(7) . . . . ? C4 C5 C6 C7 -0.8(7) . . . . ? C4 C5 C6 C6 -179.2(5) . . . 2_756 ? C5 C6 C7 C8 0.2(7) . . . . ? C6 C6 C7 C8 178.6(5) 2_756 . . . ? O3 C3 C8 C7 179.4(4) . . . . ? C4 C3 C8 C7 1.1(7) . . . . ? C6 C7 C8 C3 -0.4(8) . . . . ? O2 C1 O1 Ni1 -7.9(6) . . . . ? C2 C1 O1 Ni1 171.9(2) . . . . ? O5 Ni1 O1 C1 -161.8(3) 2 . . . ? O5 Ni1 O1 C1 18.2(3) . . . . ? O1 Ni1 O1 C1 55(100) 2 . . . ? O4 Ni1 O1 C1 -73.2(3) . . . . ? O4 Ni1 O1 C1 106.8(3) 2 . . . ? C8 C3 O3 C2 177.0(4) . . . . ? C4 C3 O3 C2 -4.9(6) . . . . ? C1 C2 O3 C3 -175.5(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O4 H4C O1 0.85 2.55 2.963(4) 110.9 . O4 H4B O1 0.85 2.04 2.882(4) 170.3 1_455 O4 H4C O3 0.85 2.48 2.989(4) 119.4 1_455 O5 H5C O2 0.85 1.87 2.688(4) 159.6 . O5 H5C O1 0.85 2.53 2.950(4) 111.5 . O5 H5A O4 0.85 2.40 2.840(4) 112.7 2_455 O5 H5A O1 0.85 2.51 3.294(4) 153.8 1_455 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.628 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.090