# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2010 data_global _journal_name_full 'New J.Chem.' _journal_coden_Cambridge 0440 _publ_contact_author_name 'Catalina Ruiz-Perez' _publ_contact_author_address ; Laboratorio de Rayos X y Materiales Moleculares Dpto. F\'isica Fundamental II. Facultad de F\'isica Universidad de La Laguna E-38204. La Laguna. Tenerife Spain ; _publ_contact_author_email caruiz@ull.es loop_ _publ_author_name M.Deniz J.Pasan O.Fabelo L.Canadillas-Delgado F.Lloret ; M.Julve ; C.Ruiz-Perez # Attachment '- compounds 2-4 and 6-8.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 779272' #TrackingRef '- compounds 2-4 and 6-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 Cl0.10 Fe N O4.90' _chemical_formula_weight 268.01 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3642(3) _cell_length_b 19.6916(8) _cell_length_c 7.3274(3) _cell_angle_alpha 90.00 _cell_angle_beta 88.250(3) _cell_angle_gamma 90.00 _cell_volume 1062.07(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 1.449 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.6704 _exptl_absorpt_correction_T_max 0.9181 _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10204 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2435 _reflns_number_gt 2008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0283P)^2^+1.1604P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2435 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0751 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.149 _refine_ls_shift/su_mean 0.025 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 O1 O -0.7219(2) 0.34093(9) 1.3345(2) 0.0284(4) Uani 1 1 d . . . O3 O -0.1557(2) 0.33700(9) 1.3284(2) 0.0297(4) Uani 1 1 d . . . C4 C -0.4326(5) 0.42823(18) 1.2839(7) 0.0568(10) Uani 1 1 d . . . H2 H -0.435(4) 0.3923(15) 1.052(4) 0.035(8) Uiso 1 1 d . . . H4B H -0.309(7) 0.454(2) 1.247(7) 0.114(17) Uiso 1 1 d . . . H4A H -0.445(6) 0.418(2) 1.434(7) 0.102(17) Uiso 1 1 d . . . H4C H -0.544(7) 0.458(2) 1.254(6) 0.100(15) Uiso 1 1 d . . . Fe1 Fe -0.44000(4) 0.212485(17) 0.96239(4) 0.01984(11) Uani 1 1 d . . . O1H O -0.4371(2) 0.29096(9) 0.7520(2) 0.0423(9) Uani 0.899(7) 1 d P . . Cl1 Cl -0.4371(2) 0.29096(9) 0.7520(2) 0.0423(9) Uani 0.101(7) 1 d P . . O4 O -0.2463(2) 0.26421(9) 1.1195(2) 0.0267(4) Uani 1 1 d . . . O2 O -0.6295(2) 0.26754(9) 1.1227(2) 0.0293(4) Uani 1 1 d . . . N1 N -0.4628(3) 0.13084(11) 1.1678(3) 0.0271(5) Uani 1 1 d . . . C7 C -0.4932(3) 0.02741(13) 1.4311(3) 0.0261(5) Uani 1 1 d . . . C3 C -0.2658(3) 0.31734(12) 1.2142(3) 0.0221(5) Uani 1 1 d . . . C1 C -0.6076(3) 0.32009(12) 1.2179(3) 0.0221(5) Uani 1 1 d . . . C2 C -0.4340(3) 0.36163(13) 1.1837(4) 0.0293(6) Uani 1 1 d . . . C8 C -0.4267(13) 0.0898(4) 1.4706(9) 0.0367(16) Uani 0.69(2) 1 d P A 1 H8 H -0.3894 0.0992 1.5881 0.044 Uiso 0.69(2) 1 calc PR A 1 C9 C -0.4141(13) 0.1394(4) 1.3373(10) 0.0378(17) Uani 0.69(2) 1 d P A 1 H9 H -0.3681 0.1816 1.3696 0.045 Uiso 0.69(2) 1 calc PR A 1 C6 C -0.5525(17) 0.0180(4) 1.2510(13) 0.054(3) Uani 0.69(2) 1 d P A 1 H6 H -0.6047 -0.0229 1.2168 0.065 Uiso 0.69(2) 1 calc PR A 1 C5 C -0.5322(18) 0.0698(4) 1.1281(13) 0.049(2) Uani 0.69(2) 1 d P A 1 H5 H -0.5687 0.0623 1.0094 0.059 Uiso 0.69(2) 1 calc PR A 1 C8A C -0.351(4) 0.0734(12) 1.426(4) 0.061(7) Uani 0.31(2) 1 d P A 2 H8A H -0.2622 0.0705 1.5132 0.074 Uiso 0.31(2) 1 calc PR A 2 C9A C -0.340(4) 0.1223(12) 1.298(4) 0.063(8) Uani 0.31(2) 1 d P A 2 H9A H -0.2414 0.1518 1.2996 0.075 Uiso 0.31(2) 1 calc PR A 2 C6A C -0.612(3) 0.0367(13) 1.308(3) 0.056(7) Uani 0.31(2) 1 d P A 2 H6A H -0.7130 0.0086 1.3069 0.068 Uiso 0.31(2) 1 calc PR A 2 C5A C -0.594(2) 0.0871(12) 1.175(3) 0.041(5) Uani 0.31(2) 1 d P A 2 H5A H -0.6813 0.0895 1.0864 0.049 Uiso 0.31(2) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0259(9) 0.0289(10) 0.0299(9) -0.0028(7) 0.0055(7) -0.0012(7) O3 0.0291(10) 0.0293(10) 0.0315(10) -0.0057(8) -0.0129(8) 0.0046(8) C4 0.0360(18) 0.0360(18) 0.099(3) -0.0107(19) -0.0078(19) -0.0011(15) Fe1 0.01685(17) 0.02387(18) 0.01889(18) 0.00136(14) -0.00210(12) -0.00137(14) O1H 0.0381(12) 0.0457(13) 0.0431(13) 0.0069(8) -0.0013(7) -0.0001(8) Cl1 0.0381(12) 0.0457(13) 0.0431(13) 0.0069(8) -0.0013(7) -0.0001(8) O4 0.0199(8) 0.0296(9) 0.0309(9) -0.0066(8) -0.0064(7) 0.0004(7) O2 0.0203(9) 0.0357(10) 0.0316(10) -0.0083(8) 0.0030(7) -0.0045(7) N1 0.0318(12) 0.0269(11) 0.0229(11) 0.0054(9) -0.0045(9) -0.0028(9) C7 0.0276(13) 0.0254(13) 0.0256(13) 0.0039(10) -0.0043(10) -0.0010(10) C3 0.0184(11) 0.0248(12) 0.0232(12) 0.0054(10) -0.0014(9) -0.0032(10) C1 0.0181(11) 0.0249(12) 0.0236(12) 0.0052(10) -0.0054(9) 0.0010(10) C2 0.0180(12) 0.0224(13) 0.0476(16) 0.0042(11) -0.0031(11) 0.0000(10) C8 0.058(4) 0.034(3) 0.019(2) 0.001(2) -0.006(3) -0.011(3) C9 0.058(5) 0.028(3) 0.027(2) 0.001(2) -0.008(3) -0.012(3) C6 0.102(7) 0.028(3) 0.034(4) 0.004(2) -0.031(4) -0.018(4) C5 0.089(7) 0.031(3) 0.030(4) 0.005(2) -0.027(4) -0.012(4) C8A 0.075(14) 0.051(11) 0.061(13) 0.033(9) -0.049(11) -0.035(10) C9A 0.067(14) 0.054(12) 0.071(14) 0.043(10) -0.047(11) -0.044(10) C6A 0.055(10) 0.063(14) 0.053(12) 0.035(9) -0.032(8) -0.050(10) C5A 0.032(8) 0.048(11) 0.044(11) 0.028(8) -0.024(6) -0.020(6) _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 O1 C1 1.250(3) . ? O1 Fe1 2.1147(17) 4_566 ? O3 C3 1.245(3) . ? O3 Fe1 2.1288(17) 4_666 ? C4 C2 1.503(4) . ? Fe1 O2 2.0979(17) . ? Fe1 O1 2.1147(17) 4_665 ? Fe1 O4 2.1206(17) . ? Fe1 O3 2.1288(17) 4_565 ? Fe1 O1H 2.1825(17) . ? Fe1 N1 2.205(2) . ? O4 C3 1.261(3) . ? O2 C1 1.261(3) . ? N1 C5A 1.292(17) . ? N1 C9 1.314(8) . ? N1 C5 1.341(9) . ? N1 C9A 1.346(18) . ? C7 C6A 1.288(19) . ? C7 C8 1.357(8) . ? C7 C8A 1.382(18) . ? C7 C6 1.414(9) . ? C7 C7 1.480(5) 3_458 ? C3 C2 1.537(3) . ? C1 C2 1.532(3) . ? C8 C9 1.383(11) . ? C6 C5 1.366(13) . ? C8A C9A 1.35(2) . ? C6A C5A 1.39(3) . ? 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 C1 O1 Fe1 128.74(16) . 4_566 ? C3 O3 Fe1 132.70(16) . 4_666 ? O2 Fe1 O1 171.20(7) . 4_665 ? O2 Fe1 O4 83.96(7) . . ? O1 Fe1 O4 88.01(7) 4_665 . ? O2 Fe1 O3 90.11(7) . 4_565 ? O1 Fe1 O3 97.77(7) 4_665 4_565 ? O4 Fe1 O3 173.66(7) . 4_565 ? O2 Fe1 O1H 91.24(7) . . ? O1 Fe1 O1H 92.76(7) 4_665 . ? O4 Fe1 O1H 92.93(7) . . ? O3 Fe1 O1H 89.41(7) 4_565 . ? O2 Fe1 N1 87.65(8) . . ? O1 Fe1 N1 88.91(7) 4_665 . ? O4 Fe1 N1 91.04(7) . . ? O3 Fe1 N1 86.48(7) 4_565 . ? O1H Fe1 N1 175.75(7) . . ? C3 O4 Fe1 129.06(15) . . ? C1 O2 Fe1 129.79(15) . . ? C5A N1 C9 105.8(10) . . ? C5A N1 C5 28.8(8) . . ? C9 N1 C5 115.9(5) . . ? C5A N1 C9A 113.9(11) . . ? C9 N1 C9A 30.3(14) . . ? C5 N1 C9A 108.1(9) . . ? C5A N1 Fe1 123.7(8) . . ? C9 N1 Fe1 122.3(4) . . ? C5 N1 Fe1 121.8(4) . . ? C9A N1 Fe1 122.4(8) . . ? C6A C7 C8 106.1(10) . . ? C6A C7 C8A 114.6(10) . . ? C8 C7 C8A 30.1(13) . . ? C6A C7 C6 29.4(12) . . ? C8 C7 C6 116.2(5) . . ? C8A C7 C6 108.5(9) . . ? C6A C7 C7 123.4(8) . 3_458 ? C8 C7 C7 122.1(4) . 3_458 ? C8A C7 C7 122.0(7) . 3_458 ? C6 C7 C7 121.7(4) . 3_458 ? O3 C3 O4 124.3(2) . . ? O3 C3 C2 117.7(2) . . ? O4 C3 C2 118.0(2) . . ? O1 C1 O2 123.6(2) . . ? O1 C1 C2 118.5(2) . . ? O2 C1 C2 117.9(2) . . ? C4 C2 C1 113.8(2) . . ? C4 C2 C3 114.0(2) . . ? C1 C2 C3 110.2(2) . . ? C7 C8 C9 120.4(6) . . ? N1 C9 C8 124.2(7) . . ? C5 C6 C7 119.2(7) . . ? N1 C5 C6 124.1(7) . . ? C9A C8A C7 121.1(14) . . ? C8A C9A N1 123.7(14) . . ? C7 C6A C5A 122.7(13) . . ? N1 C5A C6A 123.9(15) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.613 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.067 data_compound3 _database_code_depnum_ccdc_archive 'CCDC 779273' #TrackingRef '- compounds 2-4 and 6-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Mn N O5' _chemical_formula_weight 267.12 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' Mn Mn 0.3368 0.7283 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4673(3) _cell_length_b 19.4547(9) _cell_length_c 7.4182(4) _cell_angle_alpha 90.00 _cell_angle_beta 88.188(5) _cell_angle_gamma 90.00 _cell_volume 1077.13(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 1.230 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.7092 _exptl_absorpt_correction_T_max 0.7910 _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15138 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3143 _reflns_number_gt 2708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.9682P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3143 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 Mn1 Mn -0.43452(3) 0.212485(14) 0.94830(4) 0.02154(8) Uani 1 1 d . . . O1W O -0.4328(2) 0.28984(8) 0.7280(2) 0.0322(3) Uani 1 1 d . . . O4 O -0.24226(18) 0.26781(7) 1.10606(19) 0.0298(3) Uani 1 1 d . . . O2 O -0.62462(18) 0.27179(8) 1.1084(2) 0.0318(3) Uani 1 1 d . . . N1 N -0.4626(2) 0.12875(9) 1.1628(2) 0.0300(3) Uani 1 1 d . . . O1 O -0.71057(18) 0.34280(7) 1.32662(19) 0.0308(3) Uani 1 1 d . . . O3 O -0.15613(19) 0.33866(8) 1.32007(19) 0.0329(3) Uani 1 1 d . . . C4 C -0.4280(4) 0.43162(13) 1.2767(5) 0.0604(8) Uani 1 1 d . . . H4A H -0.5350 0.4569 1.2524 0.091 Uiso 1 1 calc R . . H4B H -0.3251 0.4581 1.2391 0.091 Uiso 1 1 calc R . . H4C H -0.4237 0.4225 1.4037 0.091 Uiso 1 1 calc R . . C7 C -0.4933(3) 0.02709(10) 1.4300(2) 0.0272(4) Uani 1 1 d . . . C3 C -0.2633(2) 0.32037(9) 1.2040(2) 0.0223(3) Uani 1 1 d . . . C1 C -0.6004(2) 0.32317(9) 1.2080(2) 0.0226(3) Uani 1 1 d . . . C2 C -0.4284(2) 0.36544(10) 1.1760(3) 0.0302(4) Uani 1 1 d . . . H2 H -0.4252 0.3777 1.0478 0.036 Uiso 1 1 calc R . . C8A C -0.4214(11) 0.0896(3) 1.4626(7) 0.0352(12) Uani 0.661(19) 1 d P A 1 H8A H -0.3812 0.0997 1.5770 0.042 Uiso 0.661(19) 1 calc PR A 1 C9A C -0.4070(11) 0.1386(3) 1.3277(8) 0.0372(13) Uani 0.661(19) 1 d P A 1 H9A H -0.3555 0.1807 1.3548 0.045 Uiso 0.661(19) 1 calc PR A 1 C6A C -0.5577(14) 0.0161(4) 1.2554(10) 0.048(2) Uani 0.661(19) 1 d P A 1 H6A H -0.6114 -0.0253 1.2259 0.058 Uiso 0.661(19) 1 calc PR A 1 C5A C -0.5396(15) 0.0677(4) 1.1303(11) 0.0466(19) Uani 0.661(19) 1 d P A 1 H5A H -0.5831 0.0599 1.0160 0.056 Uiso 0.661(19) 1 calc PR A 1 C9B C -0.340(3) 0.1228(8) 1.292(3) 0.051(4) Uani 0.339(19) 1 d P A 2 H9B H -0.2439 0.1532 1.2896 0.061 Uiso 0.339(19) 1 calc PR A 2 C6B C -0.6108(19) 0.0335(10) 1.301(3) 0.054(5) Uani 0.339(19) 1 d P A 2 H6B H -0.7078 0.0037 1.2976 0.065 Uiso 0.339(19) 1 calc PR A 2 C8B C -0.350(2) 0.0750(8) 1.426(2) 0.048(4) Uani 0.339(19) 1 d P A 2 H8B H -0.2634 0.0737 1.5139 0.058 Uiso 0.339(19) 1 calc PR A 2 C5B C -0.5903(17) 0.0851(10) 1.169(2) 0.045(4) Uani 0.339(19) 1 d P A 2 H5B H -0.6754 0.0876 1.0803 0.054 Uiso 0.339(19) 1 calc PR A 2 H1WB H -0.532(5) 0.2770(15) 0.668(4) 0.060(9) Uiso 1 1 d . . . H1WA H -0.344(4) 0.2795(14) 0.670(4) 0.050(8) Uiso 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 Mn1 0.01750(13) 0.02691(14) 0.02033(13) 0.00134(10) -0.00232(9) -0.00136(10) O1W 0.0239(7) 0.0397(8) 0.0331(7) 0.0063(6) -0.0002(6) 0.0015(6) O4 0.0203(6) 0.0352(7) 0.0343(7) -0.0085(6) -0.0081(5) 0.0015(5) O2 0.0193(6) 0.0384(8) 0.0373(8) -0.0102(6) 0.0040(5) -0.0049(5) N1 0.0353(9) 0.0299(8) 0.0250(8) 0.0068(6) -0.0043(7) -0.0032(7) O1 0.0262(7) 0.0331(7) 0.0328(7) -0.0042(6) 0.0046(5) -0.0026(5) O3 0.0292(7) 0.0357(8) 0.0346(7) -0.0082(6) -0.0145(6) 0.0054(6) C4 0.0368(13) 0.0369(13) 0.108(3) -0.0070(15) -0.0086(15) -0.0001(10) C7 0.0288(9) 0.0287(9) 0.0242(8) 0.0048(7) -0.0036(7) -0.0003(7) C3 0.0167(7) 0.0260(8) 0.0242(8) 0.0046(7) -0.0021(6) -0.0028(6) C1 0.0167(7) 0.0261(8) 0.0254(8) 0.0039(7) -0.0036(6) 0.0015(6) C2 0.0178(8) 0.0265(9) 0.0463(11) 0.0064(8) -0.0034(8) -0.0014(7) C8A 0.049(3) 0.037(2) 0.0202(16) 0.0023(14) -0.0085(19) -0.013(2) C9A 0.055(4) 0.030(2) 0.0264(18) 0.0038(16) -0.008(2) -0.013(2) C6A 0.080(6) 0.031(2) 0.035(3) 0.0062(18) -0.027(3) -0.015(3) C5A 0.077(6) 0.032(3) 0.032(3) 0.0051(18) -0.023(3) -0.010(3) C9B 0.058(8) 0.037(6) 0.059(8) 0.024(5) -0.033(7) -0.027(5) C6B 0.036(6) 0.069(10) 0.059(9) 0.046(7) -0.024(5) -0.038(6) C8B 0.051(7) 0.045(6) 0.050(7) 0.026(5) -0.033(6) -0.029(5) C5B 0.031(5) 0.059(9) 0.048(8) 0.034(6) -0.024(5) -0.020(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mn1 O2 2.1562(14) . ? Mn1 O1 2.1617(14) 4_665 ? Mn1 O4 2.1669(13) . ? Mn1 O3 2.1756(14) 4_565 ? Mn1 O1W 2.2213(15) . ? Mn1 N1 2.2824(16) . ? O4 C3 1.261(2) . ? O2 C1 1.260(2) . ? N1 C5B 1.276(14) . ? N1 C9A 1.318(6) . ? N1 C5A 1.345(8) . ? N1 C9B 1.351(12) . ? O1 C1 1.246(2) . ? O1 Mn1 2.1617(14) 4_566 ? O3 C3 1.246(2) . ? O3 Mn1 2.1756(14) 4_666 ? C4 C2 1.489(3) . ? C7 C6B 1.324(14) . ? C7 C8A 1.355(6) . ? C7 C6A 1.412(7) . ? C7 C8B 1.421(11) . ? C7 C7 1.481(4) 3_458 ? C3 C2 1.533(2) . ? C1 C2 1.537(2) . ? C8A C9A 1.384(8) . ? C6A C5A 1.370(11) . ? C9B C8B 1.362(16) . ? C6B C5B 1.407(19) . ? 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 Mn1 O1 169.52(6) . 4_665 ? O2 Mn1 O4 82.69(5) . . ? O1 Mn1 O4 87.46(5) 4_665 . ? O2 Mn1 O3 89.36(6) . 4_565 ? O1 Mn1 O3 100.31(6) 4_665 4_565 ? O4 Mn1 O3 171.67(6) . 4_565 ? O2 Mn1 O1W 91.78(6) . . ? O1 Mn1 O1W 92.49(6) 4_665 . ? O4 Mn1 O1W 94.14(6) . . ? O3 Mn1 O1W 88.57(6) 4_565 . ? O2 Mn1 N1 87.34(6) . . ? O1 Mn1 N1 89.36(6) 4_665 . ? O4 Mn1 N1 91.48(6) . . ? O3 Mn1 N1 85.64(6) 4_565 . ? O1W Mn1 N1 174.15(6) . . ? C3 O4 Mn1 129.88(11) . . ? C1 O2 Mn1 130.05(12) . . ? C5B N1 C9A 108.7(8) . . ? C5B N1 C5A 25.3(7) . . ? C9A N1 C5A 116.4(4) . . ? C5B N1 C9B 116.1(8) . . ? C9A N1 C9B 27.5(8) . . ? C5A N1 C9B 110.8(6) . . ? C5B N1 Mn1 123.5(6) . . ? C9A N1 Mn1 121.2(3) . . ? C5A N1 Mn1 122.4(4) . . ? C9B N1 Mn1 120.4(6) . . ? C1 O1 Mn1 128.86(13) . 4_566 ? C3 O3 Mn1 133.28(13) . 4_666 ? C6B C7 C8A 108.6(7) . . ? C6B C7 C6A 25.7(8) . . ? C8A C7 C6A 116.6(4) . . ? C6B C7 C8B 116.1(7) . . ? C8A C7 C8B 27.2(7) . . ? C6A C7 C8B 111.1(6) . . ? C6B C7 C7 122.9(6) . 3_458 ? C8A C7 C7 122.1(3) . 3_458 ? C6A C7 C7 121.2(4) . 3_458 ? C8B C7 C7 121.0(5) . 3_458 ? O3 C3 O4 123.96(17) . . ? O3 C3 C2 117.86(17) . . ? O4 C3 C2 118.16(16) . . ? O1 C1 O2 123.64(17) . . ? O1 C1 C2 118.36(17) . . ? O2 C1 C2 117.96(16) . . ? C4 C2 C3 114.34(18) . . ? C4 C2 C1 113.59(19) . . ? C3 C2 C1 110.17(15) . . ? C7 C8A C9A 120.8(5) . . ? N1 C9A C8A 123.4(5) . . ? C5A C6A C7 118.8(6) . . ? N1 C5A C6A 124.0(6) . . ? N1 C9B C8B 123.8(10) . . ? C7 C6B C5B 120.7(10) . . ? C9B C8B C7 119.0(8) . . ? N1 C5B C6B 124.3(11) . . ? 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 O1W H1WA O2 0.80(3) 1.96(3) 2.719(2) 157(3) 4_665 O1W H1WB O4 0.91(3) 1.87(3) 2.748(2) 162(3) 4_565 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.079 _refine_diff_density_min -0.423 _refine_diff_density_rms 0.065 data_compound4 _database_code_depnum_ccdc_archive 'CCDC 779274' #TrackingRef '- compounds 2-4 and 6-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Co N O5' _chemical_formula_weight 271.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3177(4) _cell_length_b 19.8049(9) _cell_length_c 7.2184(4) _cell_angle_alpha 90.00 _cell_angle_beta 88.296(4) _cell_angle_gamma 90.00 _cell_volume 1045.67(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Pink _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 1.646 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.5590 _exptl_absorpt_correction_T_max 0.6935 _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10116 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2393 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0208P)^2^+0.8601P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2393 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0240 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 Co1 Co -0.44488(3) 0.212754(11) 0.96872(3) 0.01897(8) Uani 1 1 d . . . O1W O -0.44211(19) 0.29106(7) 0.76506(19) 0.0275(3) Uani 1 1 d . . . O4 O -0.24980(16) 0.26251(6) 1.12424(17) 0.0257(3) Uani 1 1 d . . . O2 O -0.63567(16) 0.26514(7) 1.12898(18) 0.0279(3) Uani 1 1 d . . . N1 N -0.4647(2) 0.13176(8) 1.1684(2) 0.0266(3) Uani 1 1 d . . . O1 O -0.72861(17) 0.33991(6) 1.33927(17) 0.0271(3) Uani 1 1 d . . . O3 O -0.15951(17) 0.33579(6) 1.33398(17) 0.0279(3) Uani 1 1 d . . . C7 C -0.4934(3) 0.02767(9) 1.4312(2) 0.0281(4) Uani 1 1 d . . . C3 C -0.2700(2) 0.31582(8) 1.2180(2) 0.0206(3) Uani 1 1 d . . . C1 C -0.6139(2) 0.31829(8) 1.2225(2) 0.0209(3) Uani 1 1 d . . . C2 C -0.4395(2) 0.35959(9) 1.1852(3) 0.0267(4) Uani 1 1 d . . . C4 C -0.4380(3) 0.42599(11) 1.2878(4) 0.0481(6) Uani 1 1 d . . . C8B C -0.4262(5) 0.08904(14) 1.4735(4) 0.0454(9) Uani 0.811(5) 1 d P A 1 H8B H -0.3881 0.0976 1.5930 0.054 Uiso 0.811(5) 1 calc PR A 1 C9B C -0.4136(5) 0.13918(14) 1.3416(4) 0.0448(8) Uani 0.811(5) 1 d P A 1 H9B H -0.3664 0.1807 1.3763 0.054 Uiso 0.811(5) 1 calc PR A 1 C6B C -0.5555(6) 0.01969(16) 1.2530(5) 0.0664(13) Uani 0.811(5) 1 d P A 1 H6B H -0.6081 -0.0208 1.2172 0.080 Uiso 0.811(5) 1 calc PR A 1 C5B C -0.5385(6) 0.07257(16) 1.1295(5) 0.0632(13) Uani 0.811(5) 1 d P A 1 H5B H -0.5817 0.0663 1.0108 0.076 Uiso 0.811(5) 1 calc PR A 1 C8A C -0.3297(15) 0.0668(5) 1.4070(15) 0.030(2) Uiso 0.189(5) 1 d P A 2 H8A H -0.2308 0.0595 1.4825 0.036 Uiso 0.189(5) 1 calc PR A 2 C9A C -0.3208(15) 0.1156(5) 1.2700(15) 0.032(2) Uiso 0.189(5) 1 d P A 2 H9A H -0.2107 0.1381 1.2474 0.038 Uiso 0.189(5) 1 calc PR A 2 C6A C -0.6309(14) 0.0472(6) 1.3283(15) 0.029(2) Uiso 0.189(5) 1 d P A 2 H6A H -0.7439 0.0261 1.3442 0.035 Uiso 0.189(5) 1 calc PR A 2 C5A C -0.6108(14) 0.0978(6) 1.1983(15) 0.026(2) Uiso 0.189(5) 1 d P A 2 H5A H -0.7111 0.1080 1.1273 0.032 Uiso 0.189(5) 1 calc PR A 2 H2 H -0.437(3) 0.3725(12) 1.051(3) 0.042(6) Uiso 1 1 d . . . H1WB H -0.521(5) 0.2791(14) 0.701(4) 0.063(9) Uiso 1 1 d . . . H1WA H -0.339(5) 0.2809(14) 0.706(4) 0.063(9) Uiso 1 1 d . . . H4B H -0.321(4) 0.4510(15) 1.263(4) 0.072(9) Uiso 1 1 d . . . H4A H -0.442(4) 0.4176(15) 1.432(4) 0.066(9) Uiso 1 1 d . . . H4C H -0.552(5) 0.4531(18) 1.252(5) 0.095(11) Uiso 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 Co1 0.01629(11) 0.02219(12) 0.01852(12) 0.00147(8) -0.00190(8) -0.00096(8) O1W 0.0210(6) 0.0341(7) 0.0273(7) 0.0044(5) -0.0007(5) 0.0005(5) O4 0.0195(6) 0.0282(6) 0.0297(6) -0.0054(5) -0.0072(5) 0.0009(5) O2 0.0201(6) 0.0317(7) 0.0316(7) -0.0083(5) 0.0038(5) -0.0044(5) N1 0.0299(8) 0.0255(7) 0.0247(7) 0.0060(6) -0.0047(6) -0.0019(6) O1 0.0245(6) 0.0273(6) 0.0290(6) -0.0031(5) 0.0046(5) -0.0011(5) O3 0.0261(6) 0.0282(6) 0.0298(6) -0.0057(5) -0.0112(5) 0.0033(5) C7 0.0312(9) 0.0263(9) 0.0272(9) 0.0052(7) -0.0050(7) -0.0017(7) C3 0.0170(7) 0.0235(8) 0.0212(8) 0.0040(6) -0.0013(6) -0.0031(6) C1 0.0171(7) 0.0242(8) 0.0214(8) 0.0035(6) -0.0032(6) 0.0013(6) C2 0.0198(8) 0.0227(8) 0.0379(10) 0.0042(7) -0.0038(7) -0.0006(6) C4 0.0331(11) 0.0287(11) 0.0828(19) -0.0085(11) -0.0073(12) 0.0004(9) C8B 0.076(2) 0.0371(14) 0.0233(12) 0.0055(11) -0.0127(13) -0.0205(14) C9B 0.077(2) 0.0312(13) 0.0272(13) 0.0048(10) -0.0122(13) -0.0225(14) C6B 0.119(3) 0.0338(15) 0.0491(19) 0.0162(14) -0.050(2) -0.0321(19) C5B 0.116(3) 0.0365(16) 0.0402(17) 0.0139(14) -0.045(2) -0.0273(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O2 2.0659(12) . ? Co1 O4 2.0891(12) . ? Co1 O1 2.0923(12) 4_665 ? Co1 O3 2.1043(12) 4_565 ? Co1 O1W 2.1366(13) . ? Co1 N1 2.1585(14) . ? O4 C3 1.260(2) . ? O2 C1 1.263(2) . ? N1 C5A 1.276(10) . ? N1 C9B 1.324(3) . ? N1 C5B 1.324(3) . ? N1 C9A 1.339(11) . ? O1 C1 1.248(2) . ? O1 Co1 2.0923(12) 4_566 ? O3 C3 1.246(2) . ? O3 Co1 2.1043(12) 4_666 ? C7 C6A 1.326(11) . ? C7 C8B 1.349(3) . ? C7 C6B 1.386(3) . ? C7 C8A 1.433(11) . ? C7 C7 1.481(3) 3_458 ? C3 C2 1.537(2) . ? C1 C2 1.533(2) . ? C2 C4 1.509(3) . ? C8B C9B 1.377(3) . ? C6B C5B 1.379(4) . ? C8A C9A 1.383(14) . ? C6A C5A 1.378(14) . ? 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 Co1 O4 85.61(5) . . ? O2 Co1 O1 171.91(5) . 4_665 ? O4 Co1 O1 87.44(5) . 4_665 ? O2 Co1 O3 89.25(5) . 4_565 ? O4 Co1 O3 174.40(5) . 4_565 ? O1 Co1 O3 97.52(5) 4_665 4_565 ? O2 Co1 O1W 90.76(5) . . ? O4 Co1 O1W 91.99(5) . . ? O1 Co1 O1W 93.61(5) 4_665 . ? O3 Co1 O1W 90.32(5) 4_565 . ? O2 Co1 N1 88.19(6) . . ? O4 Co1 N1 91.43(5) . . ? O1 Co1 N1 87.86(5) 4_665 . ? O3 Co1 N1 86.16(5) 4_565 . ? O1W Co1 N1 176.34(6) . . ? C3 O4 Co1 127.78(11) . . ? C1 O2 Co1 128.59(11) . . ? C5A N1 C9B 99.0(5) . . ? C5A N1 C5B 39.2(5) . . ? C9B N1 C5B 115.3(2) . . ? C5A N1 C9A 116.7(7) . . ? C9B N1 C9A 42.4(5) . . ? C5B N1 C9A 103.7(5) . . ? C5A N1 Co1 122.9(5) . . ? C9B N1 Co1 122.22(14) . . ? C5B N1 Co1 122.38(15) . . ? C9A N1 Co1 120.3(5) . . ? C1 O1 Co1 127.99(11) . 4_566 ? C3 O3 Co1 132.37(11) . 4_666 ? C6A C7 C8B 98.7(5) . . ? C6A C7 C6B 40.4(5) . . ? C8B C7 C6B 116.4(2) . . ? C6A C7 C8A 114.8(6) . . ? C8B C7 C8A 39.8(4) . . ? C6B C7 C8A 104.2(5) . . ? C6A C7 C7 123.8(5) . 3_458 ? C8B C7 C7 122.1(2) . 3_458 ? C6B C7 C7 121.4(2) . 3_458 ? C8A C7 C7 121.3(5) . 3_458 ? O3 C3 O4 123.98(15) . . ? O3 C3 C2 117.84(15) . . ? O4 C3 C2 118.17(14) . . ? O1 C1 O2 123.63(15) . . ? O1 C1 C2 118.38(15) . . ? O2 C1 C2 117.96(15) . . ? C4 C2 C1 113.40(17) . . ? C4 C2 C3 113.48(16) . . ? C1 C2 C3 110.08(14) . . ? C7 C8B C9B 120.7(2) . . ? N1 C9B C8B 123.9(2) . . ? C5B C6B C7 119.2(2) . . ? N1 C5B C6B 124.4(3) . . ? C9A C8A C7 119.1(9) . . ? N1 C9A C8A 122.5(9) . . ? C7 C6A C5A 121.7(9) . . ? N1 C5A C6A 124.8(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.506 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.051 data_compound6 _database_code_depnum_ccdc_archive 'CCDC 779275' #TrackingRef '- compounds 2-4 and 6-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N O5 Zn' _chemical_formula_weight 277.55 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' Zn Zn 0.2839 1.4301 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3271(4) _cell_length_b 19.7336(12) _cell_length_c 7.2498(5) _cell_angle_alpha 90.00 _cell_angle_beta 88.286(5) _cell_angle_gamma 90.00 _cell_volume 1047.78(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 2.349 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.2552 _exptl_absorpt_correction_T_max 0.7991 _exptl_absorpt_process_details ? _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 'horizontally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8287 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.52 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2976 _reflns_number_gt 2435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0220P)^2^+0.6606P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2976 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0612 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 Zn1 Zn -0.44173(3) 0.212210(12) 0.96667(3) 0.01886(7) Uani 1 1 d . . . O1W O -0.4402(2) 0.28965(8) 0.7630(2) 0.0271(3) Uani 1 1 d . . . O4 O -0.24659(17) 0.26323(8) 1.12163(19) 0.0243(3) Uani 1 1 d . . . O2 O -0.63358(18) 0.26605(8) 1.12710(19) 0.0264(3) Uani 1 1 d . . . N1 N -0.4643(2) 0.13130(9) 1.1669(2) 0.0241(3) Uani 1 1 d . . . O1 O -0.72443(18) 0.34096(7) 1.33840(18) 0.0255(3) Uani 1 1 d . . . O3 O -0.15901(18) 0.33659(8) 1.33218(19) 0.0271(3) Uani 1 1 d . . . C7 C -0.4934(3) 0.02775(11) 1.4312(3) 0.0246(4) Uani 1 1 d . . . C3 C -0.2681(2) 0.31658(10) 1.2153(2) 0.0189(4) Uani 1 1 d . . . C1 C -0.6109(2) 0.31918(10) 1.2204(2) 0.0191(4) Uani 1 1 d . . . C2 C -0.4371(3) 0.36061(11) 1.1824(3) 0.0241(4) Uani 1 1 d . . . C4 C -0.4355(4) 0.42734(14) 1.2844(5) 0.0444(7) Uani 1 1 d . . . C8A C -0.4217(5) 0.08885(17) 1.4706(4) 0.0417(10) Uani 0.805(5) 1 d P A 1 H8A H -0.3807 0.0974 1.5884 0.050 Uiso 0.805(5) 1 calc PR A 1 C9A C -0.4089(5) 0.13862(16) 1.3376(4) 0.0421(10) Uani 0.805(5) 1 d P A 1 H9A H -0.3579 0.1800 1.3700 0.051 Uiso 0.805(5) 1 calc PR A 1 C6A C -0.5586(6) 0.0195(2) 1.2538(5) 0.0589(14) Uani 0.805(5) 1 d P A 1 H6A H -0.6137 -0.0209 1.2198 0.071 Uiso 0.805(5) 1 calc PR A 1 C5A C -0.5402(6) 0.07200(19) 1.1298(5) 0.0560(13) Uani 0.805(5) 1 d P A 1 H5A H -0.5840 0.0655 1.0121 0.067 Uiso 0.805(5) 1 calc PR A 1 C8B C -0.3287(15) 0.0677(6) 1.4051(15) 0.023(2) Uiso 0.195(5) 1 d P A 2 H8B H -0.2293 0.0603 1.4793 0.027 Uiso 0.195(5) 1 calc PR A 2 C9B C -0.3198(16) 0.1161(6) 1.2719(16) 0.026(3) Uiso 0.195(5) 1 d P A 2 H9B H -0.2110 0.1396 1.2521 0.031 Uiso 0.195(5) 1 calc PR A 2 C6B C -0.6317(14) 0.0465(6) 1.3265(15) 0.023(2) Uiso 0.195(5) 1 d P A 2 H6B H -0.7447 0.0255 1.3428 0.028 Uiso 0.195(5) 1 calc PR A 2 C5B C -0.6094(13) 0.0966(6) 1.1942(15) 0.018(2) Uiso 0.195(5) 1 d P A 2 H5B H -0.7075 0.1056 1.1196 0.022 Uiso 0.195(5) 1 calc PR A 2 H2 H -0.430(3) 0.3727(12) 1.050(3) 0.031(6) Uiso 1 1 d . . . H1WB H -0.516(4) 0.2767(14) 0.702(4) 0.041(8) Uiso 1 1 d . . . H1WA H -0.342(5) 0.2788(15) 0.702(4) 0.057(9) Uiso 1 1 d . . . H4B H -0.321(5) 0.4526(16) 1.269(4) 0.069(9) Uiso 1 1 d . . . H4A H -0.444(4) 0.4199(17) 1.425(4) 0.063(9) Uiso 1 1 d . . . H4C H -0.540(5) 0.456(2) 1.248(5) 0.090(12) Uiso 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 Zn1 0.01662(11) 0.02128(12) 0.01878(11) 0.00135(9) -0.00210(7) -0.00089(9) O1W 0.0207(7) 0.0345(9) 0.0260(7) 0.0038(7) -0.0013(6) 0.0007(6) O4 0.0183(6) 0.0259(8) 0.0290(7) -0.0062(6) -0.0079(5) 0.0008(5) O2 0.0189(6) 0.0300(8) 0.0299(7) -0.0077(6) 0.0033(5) -0.0038(6) N1 0.0274(8) 0.0220(9) 0.0232(8) 0.0046(7) -0.0041(6) -0.0018(7) O1 0.0229(7) 0.0257(8) 0.0277(7) -0.0033(6) 0.0036(5) -0.0012(6) O3 0.0252(7) 0.0265(8) 0.0303(7) -0.0058(6) -0.0121(6) 0.0032(6) C7 0.0265(9) 0.0228(11) 0.0248(9) 0.0060(8) -0.0037(7) -0.0013(8) C3 0.0159(8) 0.0209(10) 0.0198(8) 0.0030(8) -0.0014(6) -0.0036(7) C1 0.0161(8) 0.0208(10) 0.0206(9) 0.0041(8) -0.0036(7) 0.0016(7) C2 0.0191(9) 0.0200(10) 0.0332(11) 0.0030(8) -0.0035(8) -0.0011(7) C4 0.0311(12) 0.0258(13) 0.076(2) -0.0074(13) -0.0051(13) -0.0012(10) C8A 0.072(2) 0.0331(17) 0.0212(13) 0.0061(13) -0.0146(14) -0.0199(17) C9A 0.074(2) 0.0254(16) 0.0277(15) 0.0051(13) -0.0155(15) -0.0228(16) C6A 0.101(3) 0.032(2) 0.046(2) 0.0171(17) -0.043(2) -0.029(2) C5A 0.103(3) 0.031(2) 0.0366(19) 0.0121(16) -0.041(2) -0.023(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 Zn1 O2 2.0880(14) . ? Zn1 O1 2.1005(14) 4_665 ? Zn1 O4 2.1015(13) . ? Zn1 O3 2.1226(13) 4_565 ? Zn1 O1W 2.1245(15) . ? Zn1 N1 2.1611(17) . ? O4 C3 1.260(2) . ? O2 C1 1.261(2) . ? N1 C5B 1.274(10) . ? N1 C9A 1.322(3) . ? N1 C5A 1.327(4) . ? N1 C9B 1.356(11) . ? O1 C1 1.251(2) . ? O1 Zn1 2.1005(14) 4_566 ? O3 C3 1.246(2) . ? O3 Zn1 2.1226(13) 4_666 ? C7 C6B 1.336(10) . ? C7 C8A 1.349(4) . ? C7 C6A 1.395(4) . ? C7 C8B 1.450(11) . ? C7 C7 1.483(4) 3_458 ? C3 C2 1.537(3) . ? C1 C2 1.532(3) . ? C2 C4 1.510(3) . ? C8A C9A 1.377(4) . ? C6A C5A 1.375(4) . ? C8B C9B 1.358(15) . ? C6B C5B 1.384(15) . ? 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 Zn1 O1 171.70(5) . 4_665 ? O2 Zn1 O4 85.18(5) . . ? O1 Zn1 O4 87.54(5) 4_665 . ? O2 Zn1 O3 89.14(6) . 4_565 ? O1 Zn1 O3 97.99(6) 4_665 4_565 ? O4 Zn1 O3 174.03(6) . 4_565 ? O2 Zn1 O1W 90.60(6) . . ? O1 Zn1 O1W 93.64(6) 4_665 . ? O4 Zn1 O1W 92.14(6) . . ? O3 Zn1 O1W 89.75(6) 4_565 . ? O2 Zn1 N1 87.99(6) . . ? O1 Zn1 N1 88.29(6) 4_665 . ? O4 Zn1 N1 91.97(6) . . ? O3 Zn1 N1 85.98(6) 4_565 . ? O1W Zn1 N1 175.52(6) . . ? C3 O4 Zn1 127.74(12) . . ? C1 O2 Zn1 128.64(12) . . ? C5B N1 C9A 101.1(5) . . ? C5B N1 C5A 37.3(5) . . ? C9A N1 C5A 115.4(2) . . ? C5B N1 C9B 117.1(7) . . ? C9A N1 C9B 39.8(5) . . ? C5A N1 C9B 105.0(5) . . ? C5B N1 Zn1 123.2(5) . . ? C9A N1 Zn1 121.91(17) . . ? C5A N1 Zn1 122.66(16) . . ? C9B N1 Zn1 119.7(5) . . ? C1 O1 Zn1 127.63(13) . 4_566 ? C3 O3 Zn1 132.35(13) . 4_666 ? C6B C7 C8A 100.3(6) . . ? C6B C7 C6A 38.9(5) . . ? C8A C7 C6A 116.4(2) . . ? C6B C7 C8B 114.7(7) . . ? C8A C7 C8B 38.1(4) . . ? C6A C7 C8B 104.5(5) . . ? C6B C7 C7 123.5(5) . 3_458 ? C8A C7 C7 122.4(2) . 3_458 ? C6A C7 C7 121.2(3) . 3_458 ? C8B C7 C7 121.8(5) . 3_458 ? O3 C3 O4 123.95(17) . . ? O3 C3 C2 117.55(18) . . ? O4 C3 C2 118.50(16) . . ? O1 C1 O2 123.82(17) . . ? O1 C1 C2 118.16(18) . . ? O2 C1 C2 117.99(16) . . ? C4 C2 C1 113.29(18) . . ? C4 C2 C3 113.53(18) . . ? C1 C2 C3 109.84(16) . . ? C7 C8A C9A 120.5(2) . . ? N1 C9A C8A 124.1(3) . . ? C5A C6A C7 119.1(3) . . ? N1 C5A C6A 124.4(3) . . ? C9B C8B C7 119.8(9) . . ? N1 C9B C8B 122.2(10) . . ? C7 C6B C5B 121.0(9) . . ? N1 C5B C6B 124.9(9) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.316 _refine_diff_density_min -0.389 _refine_diff_density_rms 0.073 # Attachment '- compound_7.cif' data_compound7 _database_code_depnum_ccdc_archive 'CCDC 779277' #TrackingRef '- compound_7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H45 Cu2 N10 O14.50' _chemical_formula_weight 1073.90 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pc21n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, y+1/2, -z+1/2' '-x+1/2, y, z+1/2' '-x, y+1/2, -z' _cell_length_a 15.814(2) _cell_length_b 15.9037(10) _cell_length_c 18.4974(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4652.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prisms _exptl_crystal_colour Blue _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2188 _exptl_absorpt_coefficient_mu 0.995 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28031 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0829 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.59 _diffrn_reflns_theta_max 27.51 _reflns_number_total 10222 _reflns_number_gt 6732 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+4.4910P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.043(18) _refine_ls_number_reflns 10222 _refine_ls_number_parameters 639 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1117 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1250 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.003 _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 0.7115(3) 0.1165(3) 0.1718(3) 0.0255(12) Uani 1 1 d . . . C3 C 0.7098(3) 0.1182(3) 0.3114(3) 0.0249(11) Uani 1 1 d . . . C2A C 0.7461(8) 0.1604(8) 0.2427(6) 0.024(2) Uiso 0.50 1 d P A 1 H2A H 0.7338 0.2208 0.2423 0.029 Uiso 0.50 1 calc PR A 1 C4A C 0.8463(10) 0.1439(11) 0.2412(8) 0.062(4) Uiso 0.50 1 d P A 1 H4A H 0.8690 0.1626 0.1958 0.093 Uiso 0.50 1 calc PR A 1 H4B H 0.8571 0.0848 0.2469 0.093 Uiso 0.50 1 calc PR A 1 H4C H 0.8727 0.1743 0.2799 0.093 Uiso 0.50 1 calc PR A 1 C2B C 0.7568(7) 0.1279(8) 0.2419(6) 0.027(3) Uiso 0.50 1 d P A 2 H2B H 0.8021 0.0858 0.2427 0.033 Uiso 0.50 1 calc PR A 2 C4B C 0.7998(14) 0.2125(14) 0.2414(10) 0.092(6) Uiso 0.50 1 d P A 2 H4D H 0.8223 0.2234 0.1941 0.139 Uiso 0.50 1 calc PR A 2 H4E H 0.8450 0.2126 0.2761 0.139 Uiso 0.50 1 calc PR A 2 H4F H 0.7596 0.2554 0.2537 0.139 Uiso 0.50 1 calc PR A 2 C5 C 0.3994(4) 0.0363(5) 0.1672(4) 0.0492(19) Uani 1 1 d . . . H5 H 0.3913 0.0122 0.2124 0.059 Uiso 1 1 calc R . . C6 C 0.3494(4) 0.0100(5) 0.1106(4) 0.0466(18) Uani 1 1 d . . . H6 H 0.3094 -0.0322 0.1176 0.056 Uiso 1 1 calc R . . C7 C 0.3593(4) 0.0471(4) 0.0428(3) 0.0324(14) Uani 1 1 d . . . C8 C 0.4191(3) 0.1091(4) 0.0360(3) 0.0360(13) Uani 1 1 d . . . H8 H 0.4265 0.1367 -0.0079 0.043 Uiso 1 1 calc R . . C9 C 0.4685(4) 0.1303(4) 0.0957(3) 0.0404(15) Uani 1 1 d . . . H9 H 0.5099 0.1712 0.0898 0.049 Uiso 1 1 calc R . . C10 C 0.3076(4) 0.0172(4) -0.0204(4) 0.0380(16) Uani 1 1 d . . . C11 C 0.2363(5) -0.0333(5) -0.0124(4) 0.0428(18) Uani 1 1 d . . . H11 H 0.2185 -0.0484 0.0338 0.051 Uiso 1 1 calc R . . C12 C 0.1932(5) -0.0604(5) -0.0695(5) 0.059(2) Uani 1 1 d . . . H12 H 0.1455 -0.0932 -0.0611 0.071 Uiso 1 1 calc R . . C13 C 0.2799(5) 0.0039(5) -0.1457(4) 0.055(2) Uani 1 1 d . . . H13 H 0.2952 0.0181 -0.1927 0.066 Uiso 1 1 calc R . . C14 C 0.3286(5) 0.0345(5) -0.0904(4) 0.0510(19) Uani 1 1 d . . . H14 H 0.3759 0.0671 -0.1005 0.061 Uiso 1 1 calc R . . C15 C 0.4699(3) 0.0939(4) 0.3807(3) 0.0358(14) Uani 1 1 d . . . H15 H 0.5135 0.0552 0.3862 0.043 Uiso 1 1 calc R . . C16 C 0.4199(3) 0.1123(4) 0.4412(3) 0.0340(13) Uani 1 1 d . . . H16 H 0.4298 0.0854 0.4850 0.041 Uiso 1 1 calc R . . C17 C 0.3552(4) 0.1710(4) 0.4351(3) 0.0315(14) Uani 1 1 d . . . C18 C 0.3428(4) 0.2054(5) 0.3663(4) 0.0498(19) Uani 1 1 d . . . H18 H 0.2995 0.2439 0.3585 0.060 Uiso 1 1 calc R . . C19 C 0.3955(4) 0.1819(5) 0.3099(4) 0.0486(19) Uani 1 1 d . . . H19 H 0.3856 0.2053 0.2646 0.058 Uiso 1 1 calc R . . C20 C 0.3068(4) 0.1986(4) 0.4983(3) 0.0328(14) Uani 1 1 d . . . C21 C 0.3212(4) 0.1665(4) 0.5655(4) 0.0425(17) Uani 1 1 d . . . H21 H 0.3609 0.1241 0.5720 0.051 Uiso 1 1 calc R . . C22 C 0.2761(5) 0.1975(5) 0.6244(4) 0.054(2) Uani 1 1 d . . . H22 H 0.2862 0.1735 0.6694 0.065 Uiso 1 1 calc R . . C23 C 0.2061(5) 0.2892(5) 0.5537(4) 0.057(2) Uani 1 1 d . . . H23 H 0.1672 0.3327 0.5486 0.068 Uiso 1 1 calc R . . C24 C 0.2450(4) 0.2608(5) 0.4932(4) 0.047(2) Uani 1 1 d . . . H24 H 0.2305 0.2827 0.4483 0.056 Uiso 1 1 calc R . . C25 C 0.8706(4) -0.0227(4) 0.5490(3) 0.0302(14) Uani 1 1 d . . . H25 H 0.8381 -0.0114 0.5897 0.036 Uiso 1 1 calc R . . C26 C 0.9363(4) -0.0803(4) 0.5556(3) 0.0310(14) Uani 1 1 d . . . H26 H 0.9484 -0.1049 0.6001 0.037 Uiso 1 1 calc R . . C27 C 0.9844(4) -0.1010(3) 0.4940(3) 0.0230(13) Uani 1 1 d . . . C28 C 0.9649(4) -0.0590(3) 0.4311(4) 0.0273(14) Uani 1 1 d . . . H28 H 0.9962 -0.0690 0.3894 0.033 Uiso 1 1 calc R . . C29 C 0.8986(4) -0.0019(4) 0.4297(4) 0.0283(14) Uani 1 1 d . . . H29 H 0.8859 0.0246 0.3862 0.034 Uiso 1 1 calc R . . C30 C 1.0501(4) -0.1683(3) 0.4991(3) 0.0215(12) Uani 1 1 d . . . C31 C 1.1123(4) -0.1784(3) 0.4476(3) 0.0263(13) Uani 1 1 d . . . H31 H 1.1152 -0.1412 0.4088 0.032 Uiso 1 1 calc R . . C32 C 1.1093(4) -0.2887(4) 0.5583(3) 0.0297(15) Uani 1 1 d . . . H32 H 1.1075 -0.3269 0.5964 0.036 Uiso 1 1 calc R . . C33 C 1.1703(3) -0.2430(3) 0.4528(3) 0.0248(13) Uani 1 1 d . . . H33 H 1.2116 -0.2485 0.4173 0.030 Uiso 1 1 calc R . . C34 C 1.0507(4) -0.2249(4) 0.5567(3) 0.0306(15) Uani 1 1 d . . . H34 H 1.0116 -0.2195 0.5939 0.037 Uiso 1 1 calc R . . C35 C 0.6359(4) -0.0302(4) 0.5569(3) 0.0342(15) Uani 1 1 d . . . H35 H 0.6531 -0.0050 0.5999 0.041 Uiso 1 1 calc R . . C36 C 0.5768(4) -0.0942(4) 0.5598(3) 0.0349(15) Uani 1 1 d . . . H36 H 0.5559 -0.1119 0.6042 0.042 Uiso 1 1 calc R . . C37 C 0.5485(4) -0.1322(4) 0.4967(3) 0.0272(13) Uani 1 1 d . . . C38 C 0.5857(4) -0.1060(4) 0.4327(3) 0.0291(14) Uani 1 1 d . . . H38 H 0.5708 -0.1312 0.3892 0.035 Uiso 1 1 calc R . . C39 C 0.6453(4) -0.0421(3) 0.4340(3) 0.0269(14) Uani 1 1 d . . . H39 H 0.6696 -0.0262 0.3903 0.032 Uiso 1 1 calc R . . C40 C 0.4805(4) -0.1971(4) 0.4985(3) 0.0246(14) Uani 1 1 d . . . C41 C 0.4228(4) -0.1992(4) 0.5546(3) 0.0280(14) Uani 1 1 d . . . H48 H 0.4270 -0.1602 0.5919 0.034 Uiso 1 1 calc R . . C42 C 0.3591(4) -0.2583(4) 0.5559(4) 0.0284(14) Uani 1 1 d . . . H42 H 0.3204 -0.2574 0.5937 0.034 Uiso 1 1 calc R . . C43 C 0.4074(3) -0.3163(3) 0.4506(3) 0.0250(12) Uani 1 1 d . . . H43 H 0.4034 -0.3572 0.4148 0.030 Uiso 1 1 calc R . . C44 C 0.4717(3) -0.2569(3) 0.4457(3) 0.0264(13) Uani 1 1 d . . . H44 H 0.5086 -0.2577 0.4065 0.032 Uiso 1 1 calc R . . Cu1 Cu 0.54696(4) 0.11334(5) 0.23956(3) 0.03273(19) Uani 1 1 d . . . Cu2 Cu 0.75001(4) 0.09919(4) 0.49020(3) 0.02068(14) Uani 1 1 d . . . N1 N 0.4599(3) 0.0959(4) 0.1596(2) 0.0356(11) Uani 1 1 d . A . N2 N 0.2134(4) -0.0439(4) -0.1373(4) 0.0588(17) Uani 1 1 d . . . N3 N 0.4588(3) 0.1281(3) 0.3165(2) 0.0337(12) Uani 1 1 d . A . N4 N 0.2196(4) 0.2592(4) 0.6205(4) 0.0600(18) Uani 1 1 d . . . N5 N 0.8518(3) 0.0168(3) 0.4883(3) 0.0244(12) Uani 1 1 d . A . N6 N 0.3512(3) -0.3172(3) 0.5043(3) 0.0226(11) Uani 1 1 d . . . N7 N 0.6700(3) -0.0024(3) 0.4929(3) 0.0253(11) Uani 1 1 d . A . N8 N 1.1685(3) -0.2982(3) 0.5079(3) 0.0187(10) Uani 1 1 d . . . N9 N 0.5490(8) 0.3319(7) 0.2425(5) 0.100(3) Uani 1 1 d . . . N10 N 0.4294(10) 0.2047(11) 0.7819(10) 0.143(5) Uani 1 1 d . . . O1 O 0.7582(2) 0.1052(3) 0.11935(16) 0.0261(8) Uani 1 1 d . . . O2 O 0.6319(2) 0.1129(3) 0.16630(17) 0.0387(10) Uani 1 1 d . A . O3 O 0.7562(2) 0.1055(3) 0.36448(16) 0.0288(8) Uani 1 1 d . A . O4 O 0.6307(2) 0.1173(3) 0.31602(18) 0.0418(11) Uani 1 1 d . A . O5 O 0.5225(6) 0.2765(5) 0.2077(4) 0.110(3) Uani 1 1 d . . . O6 O 0.6257(9) 0.3444(12) 0.2604(9) 0.240(8) Uani 1 1 d . . . O7 O 0.5017(9) 0.3862(9) 0.2690(6) 0.177(5) Uani 1 1 d . . . O8 O 0.4543(10) 0.2314(17) 0.7292(8) 0.283(13) Uani 1 1 d . . . O9 O 0.4669(10) 0.1455(9) 0.8077(8) 0.185(5) Uani 1 1 d . . . O10 O 0.3802(8) 0.2354(9) 0.8330(7) 0.180(5) Uani 1 1 d . . . O1W O 0.5556(4) -0.0360(4) 0.2565(3) 0.0759(17) Uani 1 1 d . A . O2W O 0.6951(5) -0.1171(6) 0.1951(4) 0.137(3) Uani 1 1 d . . . O3W O 0.1636(5) 0.3766(5) 0.7265(4) 0.113(3) Uani 1 1 d . . . O4W O 0.4154(7) 0.8691(6) 0.2814(6) 0.166(4) Uani 1 1 d . . . O5W O 0.440(2) 0.0346(16) 0.6581(8) 0.33(2) Uani 0.50 1 d P . . 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 0.024(3) 0.025(3) 0.028(3) 0.004(3) 0.000(2) -0.001(2) C3 0.022(3) 0.027(3) 0.026(3) -0.004(2) 0.002(2) -0.002(2) C5 0.032(4) 0.075(5) 0.040(4) 0.020(4) -0.006(3) -0.012(4) C6 0.041(4) 0.053(4) 0.046(4) 0.011(3) -0.010(3) -0.018(3) C7 0.025(3) 0.033(3) 0.040(4) -0.002(3) -0.002(3) 0.003(3) C8 0.033(3) 0.044(4) 0.031(3) 0.007(3) -0.005(2) -0.003(3) C9 0.028(3) 0.043(4) 0.050(4) 0.011(3) 0.001(3) -0.005(3) C10 0.031(4) 0.034(4) 0.049(4) 0.001(3) -0.011(3) 0.008(3) C11 0.038(4) 0.042(4) 0.048(4) -0.009(3) -0.007(4) -0.006(3) C12 0.044(4) 0.065(5) 0.069(6) -0.007(4) -0.015(4) -0.005(4) C13 0.065(5) 0.058(5) 0.042(4) -0.003(4) -0.003(4) 0.003(4) C14 0.047(4) 0.060(5) 0.046(4) 0.002(4) -0.003(4) -0.005(4) C15 0.026(3) 0.040(3) 0.042(3) 0.000(3) 0.007(2) 0.008(3) C16 0.027(3) 0.035(3) 0.039(3) 0.003(3) 0.001(2) -0.001(3) C17 0.024(3) 0.030(3) 0.040(4) 0.001(3) 0.006(3) 0.002(3) C18 0.034(4) 0.064(5) 0.051(4) 0.012(4) 0.010(3) 0.018(3) C19 0.048(4) 0.065(5) 0.033(4) 0.008(3) 0.009(3) 0.021(4) C20 0.024(3) 0.031(3) 0.043(4) 0.002(3) 0.000(3) -0.005(3) C21 0.034(4) 0.044(4) 0.050(4) -0.012(3) 0.007(3) 0.001(3) C22 0.051(5) 0.065(5) 0.046(4) -0.011(4) 0.007(4) -0.002(4) C23 0.045(4) 0.061(5) 0.065(6) -0.026(4) 0.003(4) 0.018(4) C24 0.040(4) 0.048(4) 0.053(5) -0.010(3) 0.013(4) 0.009(4) C25 0.032(3) 0.028(3) 0.031(3) -0.007(3) 0.011(3) 0.012(3) C26 0.044(4) 0.028(3) 0.022(3) 0.003(2) -0.006(3) 0.014(3) C27 0.023(3) 0.013(2) 0.033(3) 0.000(2) 0.001(3) -0.001(2) C28 0.020(3) 0.026(3) 0.036(4) 0.005(3) 0.001(3) 0.004(2) C29 0.029(3) 0.024(3) 0.032(4) 0.002(3) 0.009(3) 0.000(3) C30 0.022(3) 0.015(3) 0.027(3) -0.004(2) -0.005(3) 0.006(3) C31 0.030(3) 0.021(3) 0.028(3) 0.000(2) -0.001(3) 0.004(3) C32 0.030(3) 0.033(3) 0.026(4) 0.011(3) -0.004(3) 0.009(3) C33 0.019(3) 0.025(3) 0.030(3) -0.001(2) 0.004(2) 0.001(2) C34 0.032(3) 0.033(3) 0.028(3) 0.002(3) 0.010(3) 0.014(3) C35 0.041(4) 0.031(3) 0.031(3) -0.003(3) -0.003(3) -0.012(3) C36 0.037(4) 0.041(4) 0.026(3) -0.004(3) 0.002(3) -0.010(3) C37 0.023(3) 0.021(3) 0.037(3) 0.004(3) 0.000(3) -0.002(3) C38 0.030(3) 0.030(3) 0.027(3) 0.000(3) -0.005(3) -0.007(3) C39 0.031(3) 0.023(3) 0.027(3) 0.003(3) 0.000(3) -0.006(3) C40 0.022(3) 0.027(3) 0.025(3) 0.003(3) -0.002(2) -0.004(3) C41 0.034(4) 0.023(3) 0.027(3) -0.008(3) 0.001(3) -0.012(3) C42 0.023(3) 0.029(3) 0.034(4) 0.003(3) 0.001(3) -0.007(3) C43 0.020(3) 0.027(3) 0.028(3) -0.003(2) -0.004(2) -0.010(2) C44 0.025(3) 0.034(3) 0.020(3) 0.000(2) 0.005(2) -0.003(3) Cu1 0.0176(3) 0.0529(5) 0.0277(3) -0.0024(5) 0.0005(3) 0.0017(4) Cu2 0.0132(2) 0.0142(2) 0.0347(3) 0.0001(5) -0.0001(2) -0.0007(3) N1 0.022(2) 0.051(3) 0.034(3) -0.001(3) -0.0041(19) 0.001(3) N2 0.051(4) 0.062(4) 0.064(5) -0.015(4) -0.014(3) -0.001(3) N3 0.021(2) 0.045(3) 0.034(3) 0.003(2) 0.001(2) 0.003(2) N4 0.045(4) 0.074(5) 0.062(4) -0.031(4) 0.008(3) 0.005(3) N5 0.021(3) 0.017(2) 0.035(3) 0.002(2) -0.009(2) 0.000(2) N6 0.016(2) 0.021(3) 0.031(3) -0.004(2) 0.002(2) -0.005(2) N7 0.018(3) 0.025(3) 0.033(3) -0.001(2) 0.001(2) -0.002(2) N8 0.015(2) 0.017(2) 0.025(3) 0.001(2) 0.0025(19) 0.002(2) N9 0.109(9) 0.095(7) 0.095(7) -0.026(6) 0.028(6) -0.021(7) N10 0.131(12) 0.150(14) 0.148(14) -0.003(12) -0.028(11) 0.030(10) O1 0.0215(17) 0.031(2) 0.0256(17) 0.000(2) 0.0028(14) 0.001(2) O2 0.0223(19) 0.069(3) 0.0248(18) -0.014(2) -0.0019(14) 0.001(2) O3 0.0266(19) 0.037(2) 0.0228(17) 0.000(2) -0.0016(14) -0.001(2) O4 0.0199(19) 0.080(3) 0.0258(18) -0.007(2) 0.0031(14) -0.007(2) O5 0.144(7) 0.088(5) 0.097(6) -0.022(5) 0.031(5) -0.026(5) O6 0.118(10) 0.260(19) 0.34(2) 0.005(12) 0.021(10) -0.010(11) O7 0.197(11) 0.165(10) 0.168(9) -0.091(8) -0.001(8) -0.002(9) O8 0.176(13) 0.53(4) 0.143(11) 0.126(17) -0.006(9) -0.076(16) O9 0.195(12) 0.143(11) 0.218(13) -0.006(9) 0.057(10) -0.006(9) O10 0.146(10) 0.231(14) 0.163(10) -0.010(9) 0.012(8) -0.022(9) O1W 0.093(5) 0.056(3) 0.079(4) 0.001(3) -0.020(3) 0.004(3) O2W 0.106(6) 0.189(9) 0.117(7) 0.046(6) -0.014(5) 0.047(6) O3W 0.131(6) 0.113(6) 0.094(5) -0.026(5) -0.003(5) 0.004(5) O4W 0.157(8) 0.105(6) 0.237(10) 0.032(7) 0.094(9) 0.016(6) O5W 0.67(6) 0.26(2) 0.046(9) 0.020(11) 0.010(17) 0.40(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.232(6) . ? C1 O2 1.265(6) . ? C1 C2B 1.493(12) . ? C1 C2A 1.584(12) . ? C3 O3 1.242(6) . ? C3 O4 1.254(6) . ? C3 C2B 1.493(12) . ? C3 C2A 1.548(12) . ? C2A C4A 1.61(2) . ? C2B C4B 1.51(3) . ? C5 N1 1.353(8) . ? C5 C6 1.377(9) . ? C6 C7 1.395(9) . ? C7 C8 1.372(8) . ? C7 C10 1.503(9) . ? C8 C9 1.394(8) . ? C9 N1 1.310(7) . ? C10 C14 1.365(10) . ? C10 C11 1.393(9) . ? C11 C12 1.328(10) . ? C12 N2 1.320(10) . ? C13 N2 1.307(10) . ? C13 C14 1.371(10) . ? C15 N3 1.318(7) . ? C15 C16 1.401(7) . ? C16 C17 1.389(8) . ? C17 C18 1.399(9) . ? C17 C20 1.465(8) . ? C18 C19 1.388(9) . ? C19 N3 1.323(8) . ? C20 C21 1.362(9) . ? C20 C24 1.393(9) . ? C21 C22 1.393(9) . ? C22 N4 1.328(9) . ? C23 N4 1.342(10) . ? C23 C24 1.355(9) . ? C25 N5 1.322(7) . ? C25 C26 1.390(8) . ? C26 C27 1.408(8) . ? C27 C28 1.377(8) . ? C27 C30 1.495(7) . ? C28 C29 1.387(8) . ? C29 N5 1.346(8) . ? C30 C31 1.379(8) . ? C30 C34 1.394(8) . ? C31 C33 1.380(7) . ? C32 N8 1.331(7) . ? C32 C34 1.375(8) . ? C33 N8 1.345(7) . ? C35 N7 1.374(7) . ? C35 C36 1.382(8) . ? C36 C37 1.389(8) . ? C37 C38 1.386(8) . ? C37 C40 1.491(8) . ? C38 C39 1.386(8) . ? C39 N7 1.319(7) . ? C40 C44 1.370(8) . ? C40 C41 1.383(8) . ? C41 C42 1.378(8) . ? C42 N6 1.343(7) . ? C43 N6 1.334(7) . ? C43 C44 1.390(7) . ? Cu1 O2 1.908(3) . ? Cu1 O4 1.939(4) . ? Cu1 N3 2.006(4) . ? Cu1 N1 2.039(4) . ? Cu1 O1W 2.399(6) . ? Cu2 N7 2.053(5) . ? Cu2 N5 2.075(5) . ? Cu2 N8 2.080(4) 4_756 ? Cu2 N6 2.083(5) 4_656 ? Cu2 O3 2.330(3) . ? Cu2 O1 2.394(3) 3_655 ? N6 Cu2 2.083(5) 4_646 ? N8 Cu2 2.080(4) 4_746 ? N9 O5 1.169(11) . ? N9 O7 1.243(14) . ? N9 O6 1.273(14) . ? N10 O8 1.134(18) . ? N10 O9 1.210(15) . ? N10 O10 1.318(17) . ? O1 Cu2 2.394(3) 3_654 ? 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 121.8(5) . . ? O1 C1 C2B 114.5(6) . . ? O2 C1 C2B 123.6(6) . . ? O1 C1 C2A 120.6(6) . . ? O2 C1 C2A 115.5(6) . . ? C2B C1 C2A 20.1(5) . . ? O3 C3 O4 122.2(5) . . ? O3 C3 C2B 113.8(6) . . ? O4 C3 C2B 123.9(6) . . ? O3 C3 C2A 120.0(6) . . ? O4 C3 C2A 115.6(6) . . ? C2B C3 C2A 20.5(5) . . ? C3 C2A C1 111.1(8) . . ? C3 C2A C4A 108.0(9) . . ? C1 C2A C4A 104.7(9) . . ? C3 C2B C1 119.7(8) . . ? C3 C2B C4B 108.8(11) . . ? C1 C2B C4B 108.7(11) . . ? N1 C5 C6 122.8(6) . . ? C5 C6 C7 119.3(6) . . ? C8 C7 C6 117.6(5) . . ? C8 C7 C10 122.0(5) . . ? C6 C7 C10 120.3(6) . . ? C7 C8 C9 119.2(5) . . ? N1 C9 C8 123.7(6) . . ? C14 C10 C11 114.4(6) . . ? C14 C10 C7 122.8(6) . . ? C11 C10 C7 122.7(6) . . ? C12 C11 C10 121.2(8) . . ? N2 C12 C11 124.6(8) . . ? N2 C13 C14 124.7(8) . . ? C10 C14 C13 120.1(7) . . ? N3 C15 C16 123.9(5) . . ? C17 C16 C15 119.4(5) . . ? C16 C17 C18 116.1(5) . . ? C16 C17 C20 121.4(5) . . ? C18 C17 C20 122.3(6) . . ? C19 C18 C17 119.6(6) . . ? N3 C19 C18 124.0(6) . . ? C21 C20 C24 116.4(6) . . ? C21 C20 C17 121.9(6) . . ? C24 C20 C17 121.7(6) . . ? C20 C21 C22 119.7(7) . . ? N4 C22 C21 124.3(7) . . ? N4 C23 C24 124.7(7) . . ? C23 C24 C20 119.9(8) . . ? N5 C25 C26 123.8(5) . . ? C25 C26 C27 119.1(5) . . ? C28 C27 C26 116.7(5) . . ? C28 C27 C30 123.8(5) . . ? C26 C27 C30 119.4(5) . . ? C27 C28 C29 120.1(6) . . ? N5 C29 C28 123.1(6) . . ? C31 C30 C34 116.6(5) . . ? C31 C30 C27 122.4(5) . . ? C34 C30 C27 121.0(5) . . ? C30 C31 C33 120.8(5) . . ? N8 C32 C34 122.8(6) . . ? N8 C33 C31 121.7(5) . . ? C32 C34 C30 119.9(6) . . ? N7 C35 C36 122.3(5) . . ? C35 C36 C37 120.5(6) . . ? C38 C37 C36 116.7(6) . . ? C38 C37 C40 122.2(5) . . ? C36 C37 C40 121.0(5) . . ? C37 C38 C39 119.7(6) . . ? N7 C39 C38 124.5(6) . . ? C44 C40 C41 116.9(5) . . ? C44 C40 C37 122.6(5) . . ? C41 C40 C37 120.6(5) . . ? C42 C41 C40 120.7(6) . . ? N6 C42 C41 122.1(6) . . ? N6 C43 C44 122.9(5) . . ? C40 C44 C43 119.9(5) . . ? O2 Cu1 O4 92.14(14) . . ? O2 Cu1 N3 173.5(2) . . ? O4 Cu1 N3 87.31(16) . . ? O2 Cu1 N1 87.71(16) . . ? O4 Cu1 N1 174.0(2) . . ? N3 Cu1 N1 93.51(17) . . ? O2 Cu1 O1W 92.8(2) . . ? O4 Cu1 O1W 84.1(2) . . ? N3 Cu1 O1W 93.6(2) . . ? N1 Cu1 O1W 89.9(2) . . ? N7 Cu2 N5 89.0(2) . . ? N7 Cu2 N8 177.6(2) . 4_756 ? N5 Cu2 N8 90.86(18) . 4_756 ? N7 Cu2 N6 91.59(19) . 4_656 ? N5 Cu2 N6 178.1(2) . 4_656 ? N8 Cu2 N6 88.52(18) 4_756 4_656 ? N7 Cu2 O3 94.83(17) . . ? N5 Cu2 O3 88.72(18) . . ? N8 Cu2 O3 87.57(17) 4_756 . ? N6 Cu2 O3 93.05(17) 4_656 . ? N7 Cu2 O1 88.48(17) . 3_655 ? N5 Cu2 O1 94.85(17) . 3_655 ? N8 Cu2 O1 89.15(17) 4_756 3_655 ? N6 Cu2 O1 83.34(16) 4_656 3_655 ? O3 Cu2 O1 175.19(16) . 3_655 ? C9 N1 C5 117.3(5) . . ? C9 N1 Cu1 121.8(4) . . ? C5 N1 Cu1 119.9(4) . . ? C13 N2 C12 115.1(7) . . ? C15 N3 C19 116.8(5) . . ? C15 N3 Cu1 119.9(4) . . ? C19 N3 Cu1 122.4(4) . . ? C22 N4 C23 114.8(6) . . ? C25 N5 C29 117.0(5) . . ? C25 N5 Cu2 117.5(4) . . ? C29 N5 Cu2 125.5(4) . . ? C43 N6 C42 117.4(5) . . ? C43 N6 Cu2 123.7(4) . 4_646 ? C42 N6 Cu2 118.9(4) . 4_646 ? C39 N7 C35 116.3(5) . . ? C39 N7 Cu2 122.6(4) . . ? C35 N7 Cu2 121.1(4) . . ? C32 N8 C33 118.2(5) . . ? C32 N8 Cu2 120.8(4) . 4_746 ? C33 N8 Cu2 120.8(4) . 4_746 ? O5 N9 O7 121.7(13) . . ? O5 N9 O6 127.0(14) . . ? O7 N9 O6 111.3(13) . . ? O8 N10 O9 117(2) . . ? O8 N10 O10 133(2) . . ? O9 N10 O10 107.2(19) . . ? C1 O1 Cu2 139.4(3) . 3_654 ? C1 O2 Cu1 130.1(3) . . ? C3 O3 Cu2 140.5(3) . . ? C3 O4 Cu1 129.2(3) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.678 _refine_diff_density_min -0.374 _refine_diff_density_rms 0.092 # Attachment '- compound_8.cif' data_compound8 _database_code_depnum_ccdc_archive 'CCDC 779278' #TrackingRef '- compound_8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H24 Cu N4 O6' _chemical_formula_weight 527.98 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4191(3) _cell_length_b 27.4874(13) _cell_length_c 11.5347(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.609(6) _cell_angle_gamma 90.00 _cell_volume 2351.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prisms _exptl_crystal_colour Blue _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1076 _exptl_absorpt_coefficient_mu 0.977 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13828 _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_sigmaI/netI 0.0841 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 4.04 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5318 _reflns_number_gt 3164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0604P)^2^+5.6136P] 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 5318 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1345 _refine_ls_R_factor_gt 0.0723 _refine_ls_wR_factor_ref 0.1764 _refine_ls_wR_factor_gt 0.1522 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.4771(7) 0.19714(17) 0.3727(4) 0.0284(10) Uani 1 1 d . . . C2 C 0.4115(7) 0.16221(17) 0.2775(4) 0.0330(11) Uani 1 1 d . . . H2 H 0.2843 0.1546 0.2897 0.040 Uiso 1 1 calc R . . C3 C 0.4261(8) 0.18912(18) 0.1620(4) 0.0334(12) Uani 1 1 d . . . C4 C 0.5188(9) 0.1148(2) 0.2800(5) 0.0528(16) Uani 1 1 d . . . H4A H 0.4734 0.0935 0.2199 0.079 Uiso 1 1 calc R . . H4B H 0.5069 0.0993 0.3540 0.079 Uiso 1 1 calc R . . H4C H 0.6437 0.1216 0.2676 0.079 Uiso 1 1 calc R . . O1 O 0.6465(4) 0.20014(11) 0.3852(3) 0.0298(7) Uani 1 1 d . . . O2 O 0.3697(5) 0.22055(14) 0.4292(3) 0.0440(9) Uani 1 1 d . . . O1W O 1.0034(5) 0.21306(15) 0.4298(3) 0.0530(11) Uani 1 1 d . . . O3 O 0.5688(6) 0.19027(16) 0.1106(3) 0.0568(11) Uani 1 1 d . . . O2W O -0.0617(7) 0.1697(2) 0.2028(5) 0.0841(16) Uani 1 1 d . . . O4 O 0.2796(5) 0.20994(12) 0.1280(3) 0.0382(9) Uani 1 1 d . . . C6 C 0.7067(8) 0.19705(18) 0.7356(4) 0.0378(12) Uani 1 1 d . . . H6 H 0.6914 0.2289 0.7605 0.045 Uiso 1 1 calc R . . C7 C 0.7049(8) 0.16077(18) 0.8172(4) 0.0382(13) Uani 1 1 d . . . H7 H 0.6870 0.1683 0.8947 0.046 Uiso 1 1 calc R . . C8 C 0.7296(7) 0.11304(17) 0.7844(4) 0.0307(11) Uani 1 1 d . . . C9 C 0.7500(8) 0.10513(18) 0.6668(4) 0.0389(13) Uani 1 1 d . . . H9 H 0.7648 0.0735 0.6399 0.047 Uiso 1 1 calc R . . C10 C 0.7487(7) 0.14289(17) 0.5894(4) 0.0363(12) Uani 1 1 d . . . H10 H 0.7619 0.1361 0.5111 0.044 Uiso 1 1 calc R . . C11 C 0.7385(7) 0.07263(18) 0.8688(4) 0.0370(12) Uani 1 1 d . . . C12 C 0.7580(12) 0.0810(2) 0.9876(5) 0.074(2) Uani 1 1 d . . . H12 H 0.7625 0.1127 1.0157 0.089 Uiso 1 1 calc R . . C13 C 0.7704(13) 0.0426(2) 1.0631(5) 0.082(3) Uani 1 1 d . . . H13 H 0.7843 0.0497 1.1416 0.098 Uiso 1 1 calc R . . C14 C 0.7508(11) -0.0109(2) 0.9212(6) 0.075(2) Uani 1 1 d . . . H14 H 0.7506 -0.0431 0.8961 0.090 Uiso 1 1 calc R . . C15 C 0.7369(11) 0.0246(2) 0.8381(6) 0.067(2) Uani 1 1 d . . . H15 H 0.7263 0.0159 0.7603 0.080 Uiso 1 1 calc R . . C16 C 0.7461(7) 0.29171(18) 0.2719(4) 0.0354(12) Uani 1 1 d . . . H16 H 0.7595 0.2595 0.2488 0.042 Uiso 1 1 calc R . . C17 C 0.7450(7) 0.32696(17) 0.1884(4) 0.0368(13) Uani 1 1 d . . . H17 H 0.7574 0.3184 0.1110 0.044 Uiso 1 1 calc R . . C18 C 0.7252(7) 0.37552(17) 0.2188(4) 0.0312(11) Uani 1 1 d . . . C19 C 0.7078(8) 0.38510(18) 0.3370(4) 0.0388(13) Uani 1 1 d . . . H19 H 0.6948 0.4169 0.3627 0.047 Uiso 1 1 calc R . . C20 C 0.7099(8) 0.34797(17) 0.4141(4) 0.0386(13) Uani 1 1 d . . . H20 H 0.6973 0.3555 0.4920 0.046 Uiso 1 1 calc R . . C21 C 0.7234(7) 0.41461(17) 0.1314(4) 0.0336(11) Uani 1 1 d . . . C22 C 0.6681(8) 0.4063(2) 0.0168(4) 0.0413(13) Uani 1 1 d . . . H22 H 0.6300 0.3755 -0.0062 0.050 Uiso 1 1 calc R . . C23 C 0.6696(9) 0.4434(2) -0.0619(5) 0.0508(16) Uani 1 1 d . . . H23 H 0.6302 0.4367 -0.1375 0.061 Uiso 1 1 calc R . . C24 C 0.7758(11) 0.4958(2) 0.0720(6) 0.068(2) Uani 1 1 d . . . H24 H 0.8123 0.5271 0.0925 0.082 Uiso 1 1 calc R . . C25 C 0.7798(9) 0.4612(2) 0.1567(5) 0.0536(16) Uani 1 1 d . . . H25 H 0.8207 0.4690 0.2313 0.064 Uiso 1 1 calc R . . Cu1 Cu 0.74396(9) 0.244570(18) 0.50198(5) 0.02730(18) Uani 1 1 d . . . N1 N 0.7290(5) 0.18941(14) 0.6227(3) 0.0290(9) Uani 1 1 d . . . N2 N 0.7642(8) -0.0033(2) 1.0331(5) 0.0644(16) Uani 1 1 d . . . N3 N 0.7291(6) 0.30079(14) 0.3854(3) 0.0310(9) Uani 1 1 d . . . N4 N 0.7233(8) 0.48815(19) -0.0380(5) 0.0594(15) 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 0.030(3) 0.032(3) 0.023(2) 0.007(2) 0.001(2) 0.000(2) C2 0.037(3) 0.033(3) 0.029(3) 0.002(2) -0.006(2) -0.009(2) C3 0.048(3) 0.034(3) 0.018(2) -0.005(2) -0.006(2) -0.007(2) C4 0.070(5) 0.035(3) 0.052(4) -0.004(3) -0.016(3) 0.004(3) O1 0.0280(19) 0.0369(19) 0.0244(16) -0.0034(14) -0.0031(13) -0.0042(15) O2 0.034(2) 0.064(3) 0.034(2) -0.0118(18) 0.0027(16) 0.0016(19) O1W 0.038(2) 0.068(3) 0.053(2) 0.012(2) 0.0053(19) 0.011(2) O3 0.059(3) 0.074(3) 0.038(2) 0.010(2) 0.005(2) -0.003(2) O2W 0.061(3) 0.098(4) 0.093(4) -0.037(3) 0.017(3) -0.014(3) O4 0.058(3) 0.0327(19) 0.0235(18) 0.0036(15) -0.0053(16) 0.0097(17) C6 0.057(4) 0.030(3) 0.026(3) -0.003(2) 0.005(2) 0.002(2) C7 0.059(4) 0.035(3) 0.021(2) -0.001(2) 0.006(2) -0.002(3) C8 0.040(3) 0.028(3) 0.024(2) 0.0009(19) -0.002(2) -0.001(2) C9 0.057(4) 0.026(3) 0.033(3) -0.005(2) -0.004(3) 0.004(2) C10 0.053(3) 0.033(3) 0.024(2) -0.001(2) 0.002(2) 0.003(2) C11 0.047(3) 0.031(3) 0.033(3) 0.003(2) -0.004(2) 0.001(2) C12 0.149(8) 0.040(3) 0.034(3) 0.004(3) 0.021(4) 0.017(4) C13 0.166(8) 0.050(4) 0.030(3) 0.013(3) 0.017(4) 0.022(5) C14 0.132(7) 0.032(3) 0.059(4) 0.007(3) -0.020(4) -0.010(4) C15 0.125(7) 0.032(3) 0.042(3) 0.003(3) -0.019(4) -0.004(4) C16 0.058(4) 0.026(2) 0.022(2) -0.004(2) 0.001(2) -0.001(2) C17 0.059(4) 0.031(3) 0.021(2) -0.003(2) 0.002(2) -0.002(2) C18 0.036(3) 0.026(3) 0.032(3) 0.000(2) -0.003(2) -0.001(2) C19 0.062(4) 0.022(2) 0.033(3) -0.001(2) 0.001(3) 0.002(2) C20 0.061(4) 0.030(3) 0.024(2) -0.005(2) -0.005(2) 0.002(2) C21 0.040(3) 0.028(3) 0.033(3) 0.005(2) 0.001(2) 0.002(2) C22 0.060(4) 0.035(3) 0.028(3) 0.002(2) 0.002(2) -0.001(3) C23 0.076(5) 0.042(3) 0.035(3) 0.010(3) 0.002(3) 0.006(3) C24 0.110(6) 0.026(3) 0.068(5) 0.008(3) -0.009(4) -0.015(4) C25 0.078(5) 0.033(3) 0.049(4) -0.002(3) -0.014(3) -0.011(3) Cu1 0.0371(3) 0.0267(3) 0.0180(2) -0.0014(3) -0.0019(2) -0.0010(3) N1 0.034(2) 0.030(2) 0.023(2) -0.0037(16) 0.0006(17) -0.0002(18) N2 0.097(5) 0.045(3) 0.051(3) 0.021(2) 0.010(3) 0.003(3) N3 0.039(3) 0.029(2) 0.025(2) -0.0025(17) -0.0016(18) 0.0023(18) N4 0.085(4) 0.045(3) 0.048(3) 0.017(2) 0.008(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.226(6) . ? C1 O1 1.264(5) . ? C1 C2 1.528(6) . ? C2 C4 1.528(7) . ? C2 C3 1.530(6) . ? C3 O3 1.228(6) . ? C3 O4 1.280(6) . ? O1 Cu1 1.943(3) . ? O1W Cu1 2.289(4) . ? O4 Cu1 1.930(3) 4_565 ? C6 N1 1.334(6) . ? C6 C7 1.372(7) . ? C7 C8 1.379(7) . ? C8 C9 1.387(7) . ? C8 C11 1.477(6) . ? C9 C10 1.369(7) . ? C10 N1 1.344(6) . ? C11 C15 1.367(7) . ? C11 C12 1.393(8) . ? C12 C13 1.369(8) . ? C13 N2 1.309(8) . ? C14 N2 1.309(8) . ? C14 C15 1.370(8) . ? C16 N3 1.342(6) . ? C16 C17 1.366(7) . ? C17 C18 1.389(6) . ? C18 C19 1.398(7) . ? C18 C21 1.473(6) . ? C19 C20 1.353(7) . ? C20 N3 1.347(6) . ? C21 C25 1.376(7) . ? C21 C22 1.392(7) . ? C22 C23 1.366(7) . ? C23 N4 1.319(7) . ? C24 N4 1.334(8) . ? C24 C25 1.363(8) . ? Cu1 O4 1.930(3) 4_666 ? Cu1 N3 2.050(4) . ? Cu1 N1 2.064(4) . ? 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 124.4(5) . . ? O2 C1 C2 120.9(5) . . ? O1 C1 C2 114.7(4) . . ? C1 C2 C4 111.6(4) . . ? C1 C2 C3 107.0(4) . . ? C4 C2 C3 112.3(5) . . ? O3 C3 O4 125.2(5) . . ? O3 C3 C2 121.0(5) . . ? O4 C3 C2 113.8(5) . . ? C1 O1 Cu1 118.0(3) . . ? C3 O4 Cu1 128.2(4) . 4_565 ? N1 C6 C7 124.0(5) . . ? C6 C7 C8 120.0(5) . . ? C7 C8 C9 115.9(4) . . ? C7 C8 C11 122.6(4) . . ? C9 C8 C11 121.5(4) . . ? C10 C9 C8 121.4(5) . . ? N1 C10 C9 122.2(5) . . ? C15 C11 C12 114.5(5) . . ? C15 C11 C8 123.8(5) . . ? C12 C11 C8 121.7(5) . . ? C13 C12 C11 120.1(6) . . ? N2 C13 C12 125.0(6) . . ? N2 C14 C15 125.3(6) . . ? C11 C15 C14 120.5(6) . . ? N3 C16 C17 123.8(5) . . ? C16 C17 C18 120.1(4) . . ? C17 C18 C19 116.1(4) . . ? C17 C18 C21 121.8(4) . . ? C19 C18 C21 122.1(4) . . ? C20 C19 C18 119.9(5) . . ? N3 C20 C19 124.3(5) . . ? C25 C21 C22 115.6(5) . . ? C25 C21 C18 122.5(5) . . ? C22 C21 C18 121.8(4) . . ? C23 C22 C21 120.1(5) . . ? N4 C23 C22 124.4(6) . . ? N4 C24 C25 124.9(6) . . ? C24 C25 C21 119.8(6) . . ? O4 Cu1 O1 165.94(15) 4_666 . ? O4 Cu1 N3 90.54(15) 4_666 . ? O1 Cu1 N3 90.39(15) . . ? O4 Cu1 N1 88.66(14) 4_666 . ? O1 Cu1 N1 88.86(14) . . ? N3 Cu1 N1 173.62(16) . . ? O4 Cu1 O1W 114.85(16) 4_666 . ? O1 Cu1 O1W 79.06(15) . . ? N3 Cu1 O1W 94.42(15) . . ? N1 Cu1 O1W 91.66(15) . . ? C6 N1 C10 116.5(4) . . ? C6 N1 Cu1 123.6(3) . . ? C10 N1 Cu1 119.8(3) . . ? C13 N2 C14 114.6(5) . . ? C16 N3 C20 115.6(4) . . ? C16 N3 Cu1 119.7(3) . . ? C20 N3 Cu1 124.7(3) . . ? C23 N4 C24 115.1(5) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.144 _refine_diff_density_min -0.453 _refine_diff_density_rms 0.098 data_Compound2 _database_code_depnum_ccdc_archive 'CCDC 787484' #TrackingRef '- compound_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8.90 Cl0.10 Fe N O4.90' _chemical_formula_weight 268.87 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' Fe Fe 0.3463 0.8444 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.3274(3) _cell_length_b 19.6916(8) _cell_length_c 7.3642(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.750(3) _cell_angle_gamma 90.00 _cell_volume 1062.07(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.681 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 547 _exptl_absorpt_coefficient_mu 1.448 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.6705 _exptl_absorpt_correction_T_max 0.9181 _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10204 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2435 _reflns_number_gt 2008 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0313P)^2^+1.0107P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2435 _refine_ls_number_parameters 186 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0494 _refine_ls_R_factor_gt 0.0351 _refine_ls_wR_factor_ref 0.0830 _refine_ls_wR_factor_gt 0.0776 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 Fe1 Fe 0.46238(4) 0.212483(17) 0.44000(4) 0.01981(11) Uani 1 1 d D . . N1 N 0.6678(3) 0.13082(11) 0.4630(3) 0.0271(5) Uani 1 1 d . . . Cl1 Cl 0.2525(2) 0.29105(9) 0.4363(3) 0.0421(4) Uani 0.10 1 d PD . . O1H O 0.2525(2) 0.29105(9) 0.4363(3) 0.0421(4) Uani 0.90 1 d PD . . O2 O 0.6227(2) 0.26753(9) 0.6296(2) 0.0293(4) Uani 1 1 d . . . O4 O 0.6195(2) 0.26425(9) 0.2464(2) 0.0269(4) Uani 1 1 d . . . O1 O 0.8346(2) 0.34091(9) 0.7219(2) 0.0283(4) Uani 1 1 d . . . O3 O 0.8284(2) 0.33696(9) 0.1556(2) 0.0297(4) Uani 1 1 d . . . C1 C 0.7180(3) 0.32009(12) 0.6077(3) 0.0221(5) Uani 1 1 d . A . C2 C 0.6843(4) 0.36173(13) 0.4341(3) 0.0289(6) Uani 1 1 d . . . H2 H 0.5540 0.3730 0.4310 0.035 Uiso 1 1 calc R A . C3 C 0.7141(3) 0.31729(12) 0.2658(3) 0.0220(5) Uani 1 1 d . A . C4 C 0.7830(6) 0.42801(16) 0.4327(5) 0.0570(9) Uani 1 1 d . A . H4A H 0.7533 0.4517 0.3217 0.086 Uiso 1 1 calc R . . H4B H 0.9122 0.4200 0.4414 0.086 Uiso 1 1 calc R . . H4C H 0.7469 0.4550 0.5342 0.086 Uiso 1 1 calc R . . C7 C 0.9313(3) 0.02746(13) 0.4933(3) 0.0261(5) Uani 1 1 d . . . C5A C 0.8374(10) 0.1394(4) 0.4138(13) 0.0384(17) Uani 0.70(2) 1 d P A 1 H5A H 0.8698 0.1816 0.3679 0.046 Uiso 0.70(2) 1 calc PR A 1 C6A C 0.9708(9) 0.0897(4) 0.4260(13) 0.0370(16) Uani 0.70(2) 1 d P A 1 H6A H 1.0880 0.0990 0.3878 0.044 Uiso 0.70(2) 1 calc PR A 1 C8A C 0.7510(12) 0.0180(4) 0.5527(17) 0.055(3) Uani 0.70(2) 1 d P A 1 H8A H 0.7166 -0.0230 0.6044 0.067 Uiso 0.70(2) 1 calc PR A 1 C9A C 0.6284(12) 0.0700(4) 0.5328(17) 0.049(2) Uani 0.70(2) 1 d P A 1 H9A H 0.5099 0.0627 0.5703 0.059 Uiso 0.70(2) 1 calc PR A 1 C5B C 0.798(4) 0.1222(12) 0.339(4) 0.059(7) Uani 0.30(2) 1 d P A 2 H5B H 0.7991 0.1518 0.2409 0.070 Uiso 0.30(2) 1 calc PR A 2 C6B C 0.925(3) 0.0735(12) 0.350(4) 0.058(7) Uani 0.30(2) 1 d P A 2 H6B H 1.0110 0.0704 0.2595 0.070 Uiso 0.30(2) 1 calc PR A 2 C8B C 0.807(3) 0.0367(13) 0.611(3) 0.054(7) Uani 0.30(2) 1 d P A 2 H8B H 0.8057 0.0082 0.7117 0.065 Uiso 0.30(2) 1 calc PR A 2 C9B C 0.675(3) 0.0876(12) 0.594(2) 0.039(5) Uani 0.30(2) 1 d P A 2 H9B H 0.5879 0.0904 0.6824 0.047 Uiso 0.30(2) 1 calc PR A 2 H1 H 0.182(6) 0.277(2) 0.537(6) 0.069(13) Uiso 0.90 1 d P . . 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 Fe1 0.01893(18) 0.02377(18) 0.01683(17) 0.00135(14) 0.00208(12) 0.00137(14) N1 0.0228(11) 0.0272(11) 0.0314(12) 0.0024(9) 0.0046(9) 0.0055(8) Cl1 0.0430(10) 0.0465(11) 0.0368(10) 0.0010(8) 0.0030(8) 0.0062(8) O1H 0.0430(10) 0.0465(11) 0.0368(10) 0.0010(8) 0.0030(8) 0.0062(8) O2 0.0317(10) 0.0357(10) 0.0204(9) 0.0045(7) -0.0029(7) -0.0081(8) O4 0.0314(9) 0.0298(9) 0.0199(8) -0.0006(7) 0.0067(7) -0.0065(8) O1 0.0300(9) 0.0286(10) 0.0259(9) 0.0010(7) -0.0054(7) -0.0026(7) O3 0.0314(10) 0.0298(10) 0.0287(9) -0.0046(8) 0.0126(7) -0.0058(8) C1 0.0236(12) 0.0248(12) 0.0182(11) -0.0009(10) 0.0053(9) 0.0051(10) C2 0.0439(15) 0.0241(13) 0.0188(12) 0.0000(10) 0.0030(10) 0.0040(11) C3 0.0231(12) 0.0247(12) 0.0183(11) 0.0032(10) 0.0015(9) 0.0049(10) C4 0.099(3) 0.0361(18) 0.0365(17) 0.0013(14) 0.0079(18) -0.0087(18) C7 0.0255(13) 0.0256(13) 0.0275(13) 0.0012(10) 0.0044(10) 0.0040(10) C5A 0.029(3) 0.028(3) 0.059(5) 0.013(3) 0.008(3) 0.001(2) C6A 0.019(2) 0.035(3) 0.058(4) 0.012(3) 0.005(2) 0.0018(19) C8A 0.034(4) 0.029(3) 0.104(7) 0.018(4) 0.032(4) 0.004(2) C9A 0.030(3) 0.032(3) 0.087(7) 0.012(4) 0.027(4) 0.006(2) C5B 0.067(14) 0.049(12) 0.062(13) 0.040(10) 0.042(10) 0.039(10) C6B 0.055(12) 0.050(11) 0.071(14) 0.034(10) 0.045(10) 0.030(9) C8B 0.052(12) 0.060(13) 0.053(10) 0.050(9) 0.031(8) 0.034(9) C9B 0.041(10) 0.049(11) 0.028(7) 0.018(6) 0.021(6) 0.027(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Fe1 O2 2.0986(17) . ? Fe1 O1 2.1143(17) 4_565 ? Fe1 O4 2.1206(16) . ? Fe1 O3 2.1280(17) 4_566 ? Fe1 Cl1 2.1811(18) . ? Fe1 N1 2.206(2) . ? N1 C9B 1.287(17) . ? N1 C5A 1.316(8) . ? N1 C9A 1.338(8) . ? N1 C5B 1.349(18) . ? O2 C1 1.261(3) . ? O4 C3 1.259(3) . ? O1 C1 1.249(3) . ? O1 Fe1 2.1143(17) 4_666 ? O3 C3 1.245(3) . ? O3 Fe1 2.1280(17) 4_665 ? C1 C2 1.533(3) . ? C2 C4 1.492(4) . ? C2 C3 1.538(3) . ? C7 C8B 1.287(19) . ? C7 C6A 1.357(7) . ? C7 C6B 1.394(18) . ? C7 C8A 1.417(9) . ? C7 C7 1.479(5) 3_756 ? C5A C6A 1.384(11) . ? C8A C9A 1.368(13) . ? C5B C6B 1.34(2) . ? C8B C9B 1.40(3) . ? 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 Fe1 O1 171.17(7) . 4_565 ? O2 Fe1 O4 83.94(7) . . ? O1 Fe1 O4 88.00(7) 4_565 . ? O2 Fe1 O3 90.09(7) . 4_566 ? O1 Fe1 O3 97.80(7) 4_565 4_566 ? O4 Fe1 O3 173.65(7) . 4_566 ? O2 Fe1 Cl1 91.27(7) . . ? O1 Fe1 Cl1 92.73(7) 4_565 . ? O4 Fe1 Cl1 92.74(7) . . ? O3 Fe1 Cl1 89.57(7) 4_566 . ? O2 Fe1 N1 87.63(8) . . ? O1 Fe1 N1 88.92(7) 4_565 . ? O4 Fe1 N1 91.07(7) . . ? O3 Fe1 N1 86.48(7) 4_566 . ? Cl1 Fe1 N1 175.90(8) . . ? C9B N1 C5A 105.8(9) . . ? C9B N1 C9A 28.9(8) . . ? C5A N1 C9A 116.0(5) . . ? C9B N1 C5B 114.1(11) . . ? C5A N1 C5B 30.5(13) . . ? C9A N1 C5B 108.2(9) . . ? C9B N1 Fe1 123.6(8) . . ? C5A N1 Fe1 122.2(4) . . ? C9A N1 Fe1 121.8(4) . . ? C5B N1 Fe1 122.3(7) . . ? C1 O2 Fe1 129.78(15) . . ? C3 O4 Fe1 129.11(15) . . ? C1 O1 Fe1 128.75(16) . 4_666 ? C3 O3 Fe1 132.72(16) . 4_665 ? O1 C1 O2 123.6(2) . . ? O1 C1 C2 118.4(2) . . ? O2 C1 C2 118.0(2) . . ? C4 C2 C1 114.1(2) . . ? C4 C2 C3 114.3(2) . . ? C1 C2 C3 110.2(2) . . ? O3 C3 O4 124.3(2) . . ? O3 C3 C2 117.6(2) . . ? O4 C3 C2 118.1(2) . . ? C8B C7 C6A 106.3(10) . . ? C8B C7 C6B 114.4(10) . . ? C6A C7 C6B 30.3(12) . . ? C8B C7 C8A 29.2(12) . . ? C6A C7 C8A 116.3(5) . . ? C6B C7 C8A 108.2(9) . . ? C8B C7 C7 123.5(8) . 3_756 ? C6A C7 C7 122.2(4) . 3_756 ? C6B C7 C7 122.2(7) . 3_756 ? C8A C7 C7 121.5(4) . 3_756 ? N1 C5A C6A 124.2(6) . . ? C7 C6A C5A 120.3(6) . . ? C9A C8A C7 118.9(6) . . ? N1 C9A C8A 124.2(7) . . ? C6B C5B N1 123.9(14) . . ? C5B C6B C7 121.0(14) . . ? C7 C8B C9B 122.8(13) . . ? N1 C9B C8B 123.8(14) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.806 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.068 # Attachment '- compound_3.cif' data_Compound3 _database_code_depnum_ccdc_archive 'CCDC 787485' #TrackingRef '- compound_3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Mn N O5' _chemical_formula_weight 267.12 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' Mn Mn 0.3368 0.7283 '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4182(4) _cell_length_b 19.4547(9) _cell_length_c 7.4673(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.812(5) _cell_angle_gamma 90.00 _cell_volume 1077.13(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour White _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.647 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 1.230 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.7092 _exptl_absorpt_correction_T_max 0.7910 _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15138 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0198 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.44 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3143 _reflns_number_gt 2708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+0.9738P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3143 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0847 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 Mn1 Mn 0.44830(4) 0.212484(14) 0.43452(3) 0.02155(8) Uani 1 1 d . . . N1 N 0.6628(2) 0.12874(9) 0.4626(2) 0.0300(3) Uani 1 1 d . . . O2 O 0.6084(2) 0.27179(8) 0.62461(18) 0.0318(3) Uani 1 1 d . . . O4 O 0.60606(19) 0.26781(7) 0.24226(18) 0.0298(3) Uani 1 1 d . . . O1W O 0.2279(2) 0.28983(8) 0.43265(19) 0.0322(3) Uani 1 1 d D . . O1 O 0.82659(19) 0.34281(7) 0.71056(19) 0.0308(3) Uani 1 1 d . . . O3 O 0.82007(19) 0.33866(8) 0.15611(19) 0.0329(3) Uani 1 1 d . . . C1 C 0.7080(2) 0.32317(9) 0.6004(2) 0.0226(3) Uani 1 1 d . A . C2 C 0.6760(3) 0.36544(10) 0.4284(2) 0.0302(4) Uani 1 1 d . . . H2 H 0.5478 0.3777 0.4252 0.036 Uiso 1 1 calc R A . C3 C 0.7040(2) 0.32037(9) 0.2633(2) 0.0223(3) Uani 1 1 d . A . C4 C 0.7767(5) 0.43162(13) 0.4279(4) 0.0605(8) Uani 1 1 d . A . H4A H 0.7489 0.4559 0.3185 0.091 Uiso 1 1 calc R . . H4B H 0.9039 0.4226 0.4368 0.091 Uiso 1 1 calc R . . H4C H 0.7423 0.4591 0.5280 0.091 Uiso 1 1 calc R . . C7 C 0.9299(2) 0.02708(10) 0.4933(3) 0.0272(4) Uani 1 1 d . . . C5A C 0.8277(7) 0.1386(3) 0.4068(11) 0.0374(13) Uani 0.668(19) 1 d P A 1 H5A H 0.8548 0.1807 0.3552 0.045 Uiso 0.668(19) 1 calc PR A 1 C6A C 0.9626(7) 0.0896(3) 0.4210(11) 0.0354(12) Uani 0.668(19) 1 d P A 1 H6A H 1.0769 0.0996 0.3805 0.043 Uiso 0.668(19) 1 calc PR A 1 C8A C 0.7556(10) 0.0161(3) 0.5581(14) 0.0481(19) Uani 0.668(19) 1 d P A 1 H8A H 0.7262 -0.0253 0.6121 0.058 Uiso 0.668(19) 1 calc PR A 1 C9A C 0.6303(10) 0.0677(4) 0.5401(14) 0.0466(19) Uani 0.668(19) 1 d P A 1 H9A H 0.5161 0.0601 0.5840 0.056 Uiso 0.668(19) 1 calc PR A 1 C5B C 0.792(3) 0.1227(8) 0.339(3) 0.050(4) Uani 0.332(19) 1 d P A 2 H5B H 0.7887 0.1529 0.2428 0.060 Uiso 0.332(19) 1 calc PR A 2 C6B C 0.925(2) 0.0748(8) 0.349(2) 0.047(4) Uani 0.332(19) 1 d P A 2 H6B H 1.0127 0.0733 0.2622 0.056 Uiso 0.332(19) 1 calc PR A 2 C8B C 0.802(3) 0.0340(10) 0.6114(18) 0.053(5) Uani 0.332(19) 1 d P A 2 H8B H 0.7988 0.0044 0.7091 0.064 Uiso 0.332(19) 1 calc PR A 2 C9B C 0.670(2) 0.0854(10) 0.5907(17) 0.044(4) Uani 0.332(19) 1 d P A 2 H9B H 0.5819 0.0881 0.6763 0.053 Uiso 0.332(19) 1 calc PR A 2 H1WA H 0.168(4) 0.2773(15) 0.530(3) 0.058(9) Uiso 1 1 d D . . H1WB H 0.166(4) 0.2784(14) 0.336(3) 0.054(9) Uiso 1 1 d 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 Mn1 0.02034(13) 0.02691(14) 0.01750(13) 0.00136(10) 0.00231(9) 0.00134(10) N1 0.0249(8) 0.0300(8) 0.0353(9) 0.0032(7) 0.0044(7) 0.0068(6) O2 0.0374(8) 0.0384(8) 0.0193(6) 0.0049(5) -0.0040(5) -0.0102(6) O4 0.0343(7) 0.0352(7) 0.0204(6) -0.0015(5) 0.0081(5) -0.0085(6) O1W 0.0331(7) 0.0395(8) 0.0240(7) -0.0014(6) 0.0005(6) 0.0064(6) O1 0.0328(7) 0.0331(7) 0.0263(7) 0.0026(6) -0.0046(5) -0.0042(6) O3 0.0346(7) 0.0357(8) 0.0292(7) -0.0054(6) 0.0145(6) -0.0082(6) C1 0.0254(8) 0.0261(8) 0.0167(7) -0.0015(6) 0.0036(6) 0.0038(7) C2 0.0463(11) 0.0265(9) 0.0179(8) 0.0014(7) 0.0034(8) 0.0063(8) C3 0.0242(8) 0.0260(8) 0.0168(7) 0.0028(6) 0.0021(6) 0.0046(7) C4 0.108(3) 0.0369(13) 0.0369(13) 0.0000(10) 0.0084(15) -0.0071(15) C7 0.0241(8) 0.0286(9) 0.0289(9) 0.0003(7) 0.0036(7) 0.0048(7) C5A 0.0265(18) 0.031(2) 0.055(4) 0.014(2) 0.009(2) 0.0038(15) C6A 0.0203(16) 0.037(2) 0.049(3) 0.013(2) 0.0087(19) 0.0024(14) C8A 0.035(3) 0.031(2) 0.079(5) 0.015(3) 0.027(3) 0.0066(18) C9A 0.031(3) 0.032(3) 0.078(6) 0.011(3) 0.023(3) 0.0054(18) C5B 0.058(8) 0.036(6) 0.057(8) 0.026(5) 0.032(6) 0.023(5) C6B 0.049(7) 0.044(6) 0.050(7) 0.027(5) 0.032(6) 0.025(5) C8B 0.058(9) 0.068(10) 0.035(5) 0.036(6) 0.023(5) 0.044(7) C9B 0.046(8) 0.058(9) 0.031(5) 0.019(5) 0.023(5) 0.032(6) _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 Mn1 O2 2.1562(14) . ? Mn1 O1 2.1618(14) 4_565 ? Mn1 O4 2.1668(13) . ? Mn1 O3 2.1754(14) 4_566 ? Mn1 O1W 2.2217(15) . ? Mn1 N1 2.2824(16) . ? N1 C9B 1.274(14) . ? N1 C5A 1.319(6) . ? N1 C9A 1.345(7) . ? N1 C5B 1.353(12) . ? O2 C1 1.259(2) . ? O4 C3 1.261(2) . ? O1 C1 1.245(2) . ? O1 Mn1 2.1618(14) 4_666 ? O3 C3 1.246(2) . ? O3 Mn1 2.1754(14) 4_665 ? C1 C2 1.537(2) . ? C2 C4 1.489(3) . ? C2 C3 1.532(2) . ? C7 C8B 1.324(14) . ? C7 C6A 1.355(6) . ? C7 C8A 1.411(7) . ? C7 C6B 1.422(11) . ? C7 C7 1.481(4) 3_756 ? C5A C6A 1.384(8) . ? C8A C9A 1.372(11) . ? C5B C6B 1.362(16) . ? C8B C9B 1.405(19) . ? 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 Mn1 O1 169.52(6) . 4_565 ? O2 Mn1 O4 82.68(5) . . ? O1 Mn1 O4 87.46(5) 4_565 . ? O2 Mn1 O3 89.37(6) . 4_566 ? O1 Mn1 O3 100.30(6) 4_565 4_566 ? O4 Mn1 O3 171.67(6) . 4_566 ? O2 Mn1 O1W 91.80(6) . . ? O1 Mn1 O1W 92.46(5) 4_565 . ? O4 Mn1 O1W 94.14(6) . . ? O3 Mn1 O1W 88.58(5) 4_566 . ? O2 Mn1 N1 87.34(6) . . ? O1 Mn1 N1 89.36(6) 4_565 . ? O4 Mn1 N1 91.48(6) . . ? O3 Mn1 N1 85.64(6) 4_566 . ? O1W Mn1 N1 174.16(6) . . ? C9B N1 C5A 108.4(7) . . ? C9B N1 C9A 25.6(7) . . ? C5A N1 C9A 116.4(4) . . ? C9B N1 C5B 116.1(8) . . ? C5A N1 C5B 27.8(8) . . ? C9A N1 C5B 110.8(6) . . ? C9B N1 Mn1 123.6(6) . . ? C5A N1 Mn1 121.2(3) . . ? C9A N1 Mn1 122.4(3) . . ? C5B N1 Mn1 120.3(5) . . ? C1 O2 Mn1 130.07(12) . . ? C3 O4 Mn1 129.87(11) . . ? C1 O1 Mn1 128.86(13) . 4_666 ? C3 O3 Mn1 133.29(13) . 4_665 ? O1 C1 O2 123.66(17) . . ? O1 C1 C2 118.36(17) . . ? O2 C1 C2 117.94(16) . . ? C4 C2 C3 114.32(18) . . ? C4 C2 C1 113.62(19) . . ? C3 C2 C1 110.17(15) . . ? O3 C3 O4 123.95(17) . . ? O3 C3 C2 117.86(17) . . ? O4 C3 C2 118.17(16) . . ? C8B C7 C6A 108.4(7) . . ? C8B C7 C8A 26.0(8) . . ? C6A C7 C8A 116.7(4) . . ? C8B C7 C6B 116.0(7) . . ? C6A C7 C6B 27.5(7) . . ? C8A C7 C6B 111.0(6) . . ? C8B C7 C7 123.0(6) . 3_756 ? C6A C7 C7 122.1(3) . 3_756 ? C8A C7 C7 121.2(4) . 3_756 ? C6B C7 C7 121.0(5) . 3_756 ? N1 C5A C6A 123.5(5) . . ? C7 C6A C5A 120.7(4) . . ? C9A C8A C7 118.8(6) . . ? N1 C9A C8A 123.9(6) . . ? N1 C5B C6B 123.6(10) . . ? C5B C6B C7 119.1(8) . . ? C7 C8B C9B 120.7(10) . . ? N1 C9B C8B 124.5(11) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.071 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.066 # Attachment '- compound_4.cif' data_Compound4 _database_code_depnum_ccdc_archive 'CCDC 787486' #TrackingRef '- compound_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Co N O5' _chemical_formula_weight 271.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Co Co 0.3494 0.9721 '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2184(4) _cell_length_b 19.8049(9) _cell_length_c 7.3177(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.704(4) _cell_angle_gamma 90.00 _cell_volume 1045.67(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Pink _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.722 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 1.646 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.5590 _exptl_absorpt_correction_T_max 0.6935 _exptl_absorpt_process_details ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10116 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0129 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2393 _reflns_number_gt 2223 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0200P)^2^+0.7599P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2393 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0225 _refine_ls_wR_factor_ref 0.0568 _refine_ls_wR_factor_gt 0.0557 _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_restrained_S_all 1.114 _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 Co1 Co 0.46873(3) 0.212753(10) 0.44488(3) 0.01896(7) Uani 1 1 d . . . N1 N 0.6684(2) 0.13176(7) 0.4647(2) 0.0265(3) Uani 1 1 d . . . O2 O 0.62902(17) 0.26513(6) 0.63569(16) 0.0279(3) Uani 1 1 d . . . O4 O 0.62420(16) 0.26252(6) 0.24984(15) 0.0257(2) Uani 1 1 d . . . O1W O 0.26495(17) 0.29104(6) 0.44225(17) 0.0273(3) Uani 1 1 d D . . O1 O 0.83927(16) 0.33991(6) 0.72862(16) 0.0270(3) Uani 1 1 d . . . O3 O 0.83400(17) 0.33578(6) 0.15950(16) 0.0279(3) Uani 1 1 d . . . C1 C 0.7224(2) 0.31829(8) 0.6139(2) 0.0209(3) Uani 1 1 d . A . C2 C 0.6853(3) 0.35961(8) 0.4394(2) 0.0266(3) Uani 1 1 d . . . H2 H 0.5529 0.3707 0.4367 0.032 Uiso 1 1 calc R A . C3 C 0.7180(2) 0.31581(8) 0.2700(2) 0.0206(3) Uani 1 1 d . A . C4 C 0.7877(4) 0.42592(10) 0.4378(3) 0.0483(6) Uani 1 1 d . A . H4A H 0.7577 0.4496 0.3263 0.072 Uiso 1 1 calc R . . H4B H 0.9187 0.4177 0.4460 0.072 Uiso 1 1 calc R . . H4C H 0.7519 0.4528 0.5401 0.072 Uiso 1 1 calc R . . C7 C 0.9312(2) 0.02770(9) 0.4934(2) 0.0280(4) Uani 1 1 d . . . C5A C 0.8430(4) 0.14009(18) 0.4182(7) 0.0375(10) Uani 0.727(10) 1 d P A 1 H5A H 0.8784 0.1821 0.3743 0.045 Uiso 0.727(10) 1 calc PR A 1 C6A C 0.9749(4) 0.08987(18) 0.4314(7) 0.0382(10) Uani 0.727(10) 1 d P A 1 H6A H 1.0955 0.0988 0.3972 0.046 Uiso 0.727(10) 1 calc PR A 1 C8A C 0.7486(7) 0.0185(2) 0.5499(10) 0.0599(15) Uani 0.727(10) 1 d P A 1 H8A H 0.7113 -0.0226 0.5981 0.072 Uiso 0.727(10) 1 calc PR A 1 C9A C 0.6257(6) 0.0715(2) 0.5326(10) 0.0557(15) Uani 0.727(10) 1 d P A 1 H9A H 0.5053 0.0648 0.5708 0.067 Uiso 0.727(10) 1 calc PR A 1 C5B C 0.784(2) 0.1188(6) 0.331(2) 0.059(5) Uani 0.273(10) 1 d P A 2 H5B H 0.7717 0.1442 0.2243 0.071 Uiso 0.273(10) 1 calc PR A 2 C6B C 0.920(2) 0.0701(6) 0.3400(19) 0.056(4) Uani 0.273(10) 1 d P A 2 H6B H 1.0024 0.0653 0.2459 0.068 Uiso 0.273(10) 1 calc PR A 2 C8B C 0.8171(18) 0.0423(7) 0.6228(15) 0.051(4) Uani 0.273(10) 1 d P A 2 H8B H 0.8224 0.0173 0.7304 0.062 Uiso 0.273(10) 1 calc PR A 2 C9B C 0.6892(17) 0.0936(7) 0.6049(14) 0.044(3) Uani 0.273(10) 1 d P A 2 H9B H 0.6117 0.1010 0.7022 0.052 Uiso 0.273(10) 1 calc PR A 2 H1WA H 0.195(4) 0.2782(13) 0.530(3) 0.067(9) Uiso 1 1 d D . . H1WB H 0.206(4) 0.2804(13) 0.339(3) 0.061(8) Uiso 1 1 d 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 Co1 0.01852(11) 0.02217(12) 0.01627(11) 0.00096(8) 0.00190(8) 0.00146(8) N1 0.0246(7) 0.0254(7) 0.0298(7) 0.0018(6) 0.0049(6) 0.0061(6) O2 0.0317(6) 0.0317(6) 0.0199(6) 0.0045(5) -0.0038(5) -0.0082(5) O4 0.0297(6) 0.0282(6) 0.0196(5) -0.0007(5) 0.0072(5) -0.0053(5) O1W 0.0272(6) 0.0339(7) 0.0208(6) -0.0006(5) 0.0003(5) 0.0043(5) O1 0.0290(6) 0.0273(6) 0.0246(6) 0.0011(5) -0.0046(5) -0.0030(5) O3 0.0298(6) 0.0283(6) 0.0261(6) -0.0032(5) 0.0112(5) -0.0056(5) C1 0.0214(7) 0.0241(8) 0.0173(7) -0.0014(6) 0.0031(6) 0.0036(6) C2 0.0371(9) 0.0230(8) 0.0198(7) 0.0005(6) 0.0039(7) 0.0042(7) C3 0.0213(7) 0.0234(7) 0.0171(7) 0.0030(6) 0.0015(6) 0.0039(6) C4 0.0832(17) 0.0288(10) 0.0332(10) -0.0007(8) 0.0070(11) -0.0077(10) C7 0.0269(8) 0.0262(8) 0.0312(9) 0.0017(7) 0.0050(7) 0.0053(7) C5A 0.0250(14) 0.0266(15) 0.061(3) 0.0132(16) 0.0064(14) 0.0019(11) C6A 0.0218(13) 0.0340(16) 0.059(3) 0.0126(16) 0.0065(14) 0.0026(11) C8A 0.040(2) 0.0287(18) 0.113(4) 0.021(2) 0.040(2) 0.0082(15) C9A 0.033(2) 0.0321(19) 0.104(4) 0.018(2) 0.033(2) 0.0082(14) C5B 0.083(9) 0.045(6) 0.053(7) 0.030(5) 0.041(7) 0.034(6) C6B 0.065(8) 0.054(7) 0.053(7) 0.026(6) 0.044(6) 0.035(6) C8B 0.053(7) 0.058(7) 0.045(6) 0.042(5) 0.026(5) 0.029(6) C9B 0.042(6) 0.055(7) 0.035(5) 0.020(4) 0.024(4) 0.022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 O1 2.0923(12) 4_565 ? Co1 O4 2.0888(11) . ? Co1 O2 2.0660(12) . ? Co1 O3 2.1040(12) 4_566 ? Co1 O1W 2.1369(12) . ? Co1 N1 2.1586(14) . ? N1 C9B 1.280(9) . ? N1 C5A 1.326(3) . ? N1 C5B 1.329(9) . ? N1 C9A 1.332(4) . ? O2 C1 1.263(2) . ? O4 C3 1.260(2) . ? O1 C1 1.2482(19) . ? O1 Co1 2.0923(12) 4_666 ? O3 C3 1.2456(19) . ? O3 Co1 2.1040(12) 4_665 ? C1 C2 1.533(2) . ? C2 C4 1.507(3) . ? C2 C3 1.537(2) . ? C7 C8B 1.306(10) . ? C7 C6A 1.353(4) . ? C7 C6B 1.402(10) . ? C7 C8A 1.405(4) . ? C7 C7 1.481(3) 3_756 ? C5A C6A 1.378(4) . ? C8A C9A 1.378(5) . ? C5B C6B 1.375(13) . ? C8B C9B 1.376(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O4 87.44(5) 4_565 . ? O1 Co1 O2 171.91(5) 4_565 . ? O4 Co1 O2 85.61(5) . . ? O1 Co1 O3 97.52(5) 4_565 4_566 ? O4 Co1 O3 174.39(5) . 4_566 ? O2 Co1 O3 89.25(5) . 4_566 ? O1 Co1 O1W 93.62(5) 4_565 . ? O4 Co1 O1W 92.01(5) . . ? O2 Co1 O1W 90.76(5) . . ? O3 Co1 O1W 90.28(5) 4_566 . ? O1 Co1 N1 87.86(5) 4_565 . ? O4 Co1 N1 91.46(5) . . ? O2 Co1 N1 88.18(5) . . ? O3 Co1 N1 86.15(5) 4_566 . ? O1W Co1 N1 176.29(5) . . ? C9B N1 C5A 100.9(5) . . ? C9B N1 C5B 114.5(6) . . ? C5A N1 C5B 38.2(8) . . ? C9B N1 C9A 36.3(6) . . ? C5A N1 C9A 116.1(2) . . ? C5B N1 C9A 105.0(5) . . ? C9B N1 Co1 123.7(4) . . ? C5A N1 Co1 121.89(16) . . ? C5B N1 Co1 121.7(4) . . ? C9A N1 Co1 121.96(18) . . ? C1 O2 Co1 128.57(10) . . ? C3 O4 Co1 127.80(10) . . ? C1 O1 Co1 127.98(11) . 4_666 ? C3 O3 Co1 132.38(11) . 4_665 ? O1 C1 O2 123.62(15) . . ? O1 C1 C2 118.35(14) . . ? O2 C1 C2 118.00(14) . . ? C4 C2 C1 113.46(15) . . ? C4 C2 C3 113.46(15) . . ? C1 C2 C3 110.06(13) . . ? O3 C3 O4 123.99(15) . . ? O3 C3 C2 117.83(14) . . ? O4 C3 C2 118.17(14) . . ? C8B C7 C6A 101.5(6) . . ? C8B C7 C6B 115.1(5) . . ? C6A C7 C6B 36.5(7) . . ? C8B C7 C8A 36.7(6) . . ? C6A C7 C8A 116.6(2) . . ? C6B C7 C8A 106.2(5) . . ? C8B C7 C7 123.6(4) . 3_756 ? C6A C7 C7 122.2(2) . 3_756 ? C6B C7 C7 121.3(4) . 3_756 ? C8A C7 C7 121.2(2) . 3_756 ? N1 C5A C6A 123.5(3) . . ? C7 C6A C5A 120.8(3) . . ? C9A C8A C7 118.7(3) . . ? N1 C9A C8A 124.2(3) . . ? N1 C5B C6B 124.1(8) . . ? C5B C6B C7 119.0(7) . . ? C7 C8B C9B 122.0(7) . . ? N1 C9B C8B 125.1(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.524 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.049 # Attachment '- compound_6.cif' data_Compound6 _database_code_depnum_ccdc_archive 'CCDC 787487' #TrackingRef '- compound_6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 N O5 Zn' _chemical_formula_weight 277.55 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' Zn Zn 0.2839 1.4301 '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 P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.2498(5) _cell_length_b 19.7336(12) _cell_length_c 7.3271(4) _cell_angle_alpha 90.00 _cell_angle_beta 91.714(5) _cell_angle_gamma 90.00 _cell_volume 1047.78(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.759 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 2.349 _exptl_absorpt_correction_type sphere _exptl_absorpt_correction_T_min 0.2552 _exptl_absorpt_correction_T_max 0.7991 _exptl_absorpt_process_details ? _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_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8287 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.52 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2976 _reflns_number_gt 2435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0204P)^2^+0.5732P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2976 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.0633 _refine_ls_wR_factor_gt 0.0593 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.063 _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 Zn1 Zn 0.46667(3) 0.212210(11) 0.44173(3) 0.01888(7) Uani 1 1 d . . . N1 N 0.6670(2) 0.13129(9) 0.4644(2) 0.0241(3) Uani 1 1 d . . . O2 O 0.62710(19) 0.26606(8) 0.63356(17) 0.0263(3) Uani 1 1 d . . . O4 O 0.62162(18) 0.26322(7) 0.24660(17) 0.0243(3) Uani 1 1 d . . . O1W O 0.26290(19) 0.28961(8) 0.44033(19) 0.0268(3) Uani 1 1 d D . . O1 O 0.83846(18) 0.34095(7) 0.72446(17) 0.0255(3) Uani 1 1 d . . . O3 O 0.83223(18) 0.33661(7) 0.15905(18) 0.0271(3) Uani 1 1 d . . . C1 C 0.7204(2) 0.31914(10) 0.6109(2) 0.0191(4) Uani 1 1 d . A . C2 C 0.6824(3) 0.36062(10) 0.4370(2) 0.0240(4) Uani 1 1 d . . . H2 H 0.5506 0.3716 0.4344 0.029 Uiso 1 1 calc R A . C3 C 0.7154(2) 0.31658(10) 0.2681(2) 0.0189(4) Uani 1 1 d . A . C4 C 0.7845(4) 0.42732(12) 0.4354(3) 0.0447(6) Uani 1 1 d . A . H4A H 0.7547 0.4511 0.3241 0.067 Uiso 1 1 calc R . . H4B H 0.9150 0.4190 0.4437 0.067 Uiso 1 1 calc R . . H4C H 0.7488 0.4543 0.5376 0.067 Uiso 1 1 calc R . . C7 C 0.9312(3) 0.02775(10) 0.4934(3) 0.0244(4) Uani 1 1 d . . . C5A C 0.8392(5) 0.1397(2) 0.4145(9) 0.0355(11) Uani 0.717(12) 1 d P A 1 H5A H 0.8726 0.1817 0.3685 0.043 Uiso 0.717(12) 1 calc PR A 1 C6A C 0.9725(5) 0.0896(2) 0.4267(8) 0.0348(11) Uani 0.717(12) 1 d P A 1 H6A H 1.0914 0.0986 0.3889 0.042 Uiso 0.717(12) 1 calc PR A 1 C8A C 0.7499(7) 0.0181(3) 0.5528(10) 0.0521(16) Uani 0.717(12) 1 d P A 1 H8A H 0.7147 -0.0230 0.6031 0.063 Uiso 0.717(12) 1 calc PR A 1 C9A C 0.6256(7) 0.0710(2) 0.5346(10) 0.0490(15) Uani 0.717(12) 1 d P A 1 H9A H 0.5062 0.0641 0.5737 0.059 Uiso 0.717(12) 1 calc PR A 1 C5B C 0.786(2) 0.1195(7) 0.331(2) 0.049(4) Uani 0.283(12) 1 d P A 2 H5B H 0.7785 0.1467 0.2274 0.059 Uiso 0.283(12) 1 calc PR A 2 C6B C 0.916(2) 0.0706(7) 0.339(2) 0.046(4) Uani 0.283(12) 1 d P A 2 H6B H 0.9949 0.0650 0.2426 0.055 Uiso 0.283(12) 1 calc PR A 2 C8B C 0.815(2) 0.0423(8) 0.6236(16) 0.044(4) Uani 0.283(12) 1 d P A 2 H8B H 0.8208 0.0176 0.7317 0.053 Uiso 0.283(12) 1 calc PR A 2 C9B C 0.6869(16) 0.0925(7) 0.6037(14) 0.034(3) Uani 0.283(12) 1 d P A 2 H9B H 0.6072 0.0991 0.6992 0.041 Uiso 0.283(12) 1 calc PR A 2 H1WA H 0.196(3) 0.2751(13) 0.526(3) 0.047(8) Uiso 1 1 d D . . H1WB H 0.200(4) 0.2781(14) 0.340(3) 0.056(9) Uiso 1 1 d 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 Zn1 0.01880(11) 0.02129(12) 0.01663(10) 0.00088(8) 0.00211(7) 0.00134(9) N1 0.0231(8) 0.0218(9) 0.0276(8) 0.0017(7) 0.0043(6) 0.0046(7) O2 0.0300(7) 0.0300(8) 0.0187(6) 0.0039(5) -0.0033(5) -0.0076(6) O4 0.0291(7) 0.0260(8) 0.0182(6) -0.0008(5) 0.0079(5) -0.0060(6) O1W 0.0257(7) 0.0341(9) 0.0207(7) -0.0009(6) 0.0009(6) 0.0037(6) O1 0.0277(7) 0.0256(8) 0.0228(7) 0.0012(6) -0.0036(5) -0.0033(6) O3 0.0303(7) 0.0267(8) 0.0251(7) -0.0033(6) 0.0122(6) -0.0058(6) C1 0.0205(8) 0.0208(10) 0.0160(8) -0.0016(7) 0.0036(6) 0.0043(7) C2 0.0330(10) 0.0201(10) 0.0191(8) 0.0011(7) 0.0039(7) 0.0029(8) C3 0.0200(8) 0.0207(10) 0.0160(8) 0.0037(7) 0.0013(6) 0.0029(8) C4 0.0770(18) 0.0263(13) 0.0309(11) 0.0009(9) 0.0044(12) -0.0066(12) C7 0.0246(9) 0.0226(11) 0.0262(9) 0.0013(8) 0.0037(7) 0.0060(8) C5A 0.0267(17) 0.0213(19) 0.059(3) 0.0127(19) 0.0104(17) 0.0019(14) C6A 0.0180(15) 0.030(2) 0.057(3) 0.0123(19) 0.0072(16) 0.0026(14) C8A 0.040(3) 0.025(2) 0.093(4) 0.016(2) 0.035(3) 0.0096(18) C9A 0.028(2) 0.027(2) 0.093(4) 0.015(2) 0.029(3) 0.0061(17) C5B 0.071(9) 0.033(7) 0.046(7) 0.026(5) 0.037(7) 0.033(6) C6B 0.050(7) 0.038(7) 0.051(7) 0.026(6) 0.033(6) 0.024(6) C8B 0.057(8) 0.044(8) 0.034(5) 0.028(5) 0.028(5) 0.029(6) C9B 0.026(5) 0.048(8) 0.029(5) 0.018(4) 0.020(4) 0.019(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 O2 2.0880(14) . ? Zn1 O1 2.1000(13) 4_565 ? Zn1 O4 2.1013(13) . ? Zn1 O3 2.1229(13) 4_566 ? Zn1 O1W 2.1248(15) . ? Zn1 N1 2.1614(16) . ? N1 C9B 1.281(9) . ? N1 C5A 1.322(4) . ? N1 C9A 1.335(5) . ? N1 C5B 1.342(9) . ? O2 C1 1.261(2) . ? O4 C3 1.261(2) . ? O1 C1 1.252(2) . ? O1 Zn1 2.1000(13) 4_666 ? O3 C3 1.246(2) . ? O3 Zn1 2.1229(13) 4_665 ? C1 C2 1.532(3) . ? C2 C4 1.510(3) . ? C2 C3 1.536(3) . ? C7 C8B 1.324(9) . ? C7 C6A 1.352(4) . ? C7 C8A 1.409(5) . ? C7 C6B 1.415(10) . ? C7 C7 1.483(4) 3_756 ? C5A C6A 1.383(5) . ? C8A C9A 1.382(6) . ? C5B C6B 1.347(13) . ? C8B C9B 1.362(14) . ? 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 Zn1 O1 171.69(5) . 4_565 ? O2 Zn1 O4 85.17(5) . . ? O1 Zn1 O4 87.53(5) 4_565 . ? O2 Zn1 O3 89.14(5) . 4_566 ? O1 Zn1 O3 98.00(6) 4_565 4_566 ? O4 Zn1 O3 174.02(5) . 4_566 ? O2 Zn1 O1W 90.61(6) . . ? O1 Zn1 O1W 93.64(5) 4_565 . ? O4 Zn1 O1W 92.18(6) . . ? O3 Zn1 O1W 89.72(5) 4_566 . ? O2 Zn1 N1 87.99(6) . . ? O1 Zn1 N1 88.29(6) 4_565 . ? O4 Zn1 N1 91.98(6) . . ? O3 Zn1 N1 85.96(6) 4_566 . ? O1W Zn1 N1 175.48(6) . . ? C9B N1 C5A 102.2(5) . . ? C9B N1 C9A 35.0(5) . . ? C5A N1 C9A 116.3(3) . . ? C9B N1 C5B 114.6(6) . . ? C5A N1 C5B 35.7(8) . . ? C9A N1 C5B 106.4(5) . . ? C9B N1 Zn1 124.2(4) . . ? C5A N1 Zn1 121.6(2) . . ? C9A N1 Zn1 122.0(2) . . ? C5B N1 Zn1 121.1(5) . . ? C1 O2 Zn1 128.64(11) . . ? C3 O4 Zn1 127.75(11) . . ? C1 O1 Zn1 127.63(13) . 4_666 ? C3 O3 Zn1 132.31(13) . 4_665 ? O1 C1 O2 123.82(16) . . ? O1 C1 C2 118.12(17) . . ? O2 C1 C2 118.02(16) . . ? C4 C2 C1 113.32(17) . . ? C4 C2 C3 113.52(16) . . ? C1 C2 C3 109.82(16) . . ? O3 C3 O4 123.99(17) . . ? O3 C3 C2 117.51(17) . . ? O4 C3 C2 118.49(15) . . ? C8B C7 C6A 102.6(6) . . ? C8B C7 C8A 35.6(6) . . ? C6A C7 C8A 116.9(3) . . ? C8B C7 C6B 114.2(6) . . ? C6A C7 C6B 35.4(7) . . ? C8A C7 C6B 106.0(5) . . ? C8B C7 C7 123.7(5) . 3_756 ? C6A C7 C7 122.3(3) . 3_756 ? C8A C7 C7 120.8(3) . 3_756 ? C6B C7 C7 122.1(4) . 3_756 ? N1 C5A C6A 123.8(3) . . ? C7 C6A C5A 120.4(3) . . ? C9A C8A C7 118.7(4) . . ? N1 C9A C8A 123.8(4) . . ? N1 C5B C6B 123.8(8) . . ? C5B C6B C7 120.1(7) . . ? C7 C8B C9B 121.8(8) . . ? N1 C9B C8B 125.5(8) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.322 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.071