# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Zheng, Hegen' _publ_contact_author_email zhenghg@nju.edu.cn _publ_section_title ; Syntheses, structures, magnetic and photoluminescence properties of metal-organic frameworks based on aromatic polycarboxylate acids ; loop_ _publ_author_name 'Zhao-Rui Pan' 'Jiao Xu' 'Xiaoqiang Yao' 'Yizhi Li' 'Zijian Guo' ; Hegen Zheng ; # Attachment '- 1.cif' data_yy1 _database_code_depnum_ccdc_archive 'CCDC 759542' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H6 Co O8' _chemical_formula_sum 'C16 H6 Co O8' _chemical_formula_weight 385.14 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.678(3) _cell_length_b 9.1970(19) _cell_length_c 9.414(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1357.4(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 27.62 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.885 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 1.314 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.77 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6732 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1341 _reflns_number_gt 1082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1341 _refine_ls_number_parameters 114 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0447 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0807 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 O4 O 0.36414(11) 0.45673(19) 0.2117(2) 0.0286(5) Uani 1 1 d . . . C1 C 0.31139(17) 0.4041(3) 0.1312(3) 0.0246(6) Uani 1 1 d . . . O3 O -0.02531(11) 0.11089(18) 0.09666(17) 0.0189(4) Uani 1 1 d . . . Co1 Co 0.0000 0.04560(5) -0.2500 0.01699(17) Uani 1 2 d S . . O1 O 0.03194(12) 0.20124(19) -0.10119(18) 0.0249(4) Uani 1 1 d . . . C3 C 0.08051(15) 0.2929(3) 0.1186(3) 0.0180(6) Uani 1 1 d . . . C4 C 0.16596(16) 0.3048(3) 0.0849(3) 0.0218(6) Uani 1 1 d . . . H4A H 0.1877 0.2566 0.0059 0.026 Uiso 1 1 calc R . . O5 O 0.32825(12) 0.3597(2) 0.0036(2) 0.0427(6) Uani 1 1 d . . . C6 C 0.18640(17) 0.4613(3) 0.2849(3) 0.0296(7) Uani 1 1 d . . . H6A H 0.2221 0.5159 0.3431 0.036 Uiso 1 1 calc R . . C2 C 0.02585(16) 0.1946(3) 0.0304(3) 0.0187(6) Uani 1 1 d . . . C7 C 0.10051(17) 0.4529(3) 0.3146(3) 0.0296(7) Uani 1 1 d . . . H7A H 0.0785 0.5050 0.3909 0.035 Uiso 1 1 calc R . . C5 C 0.21960(15) 0.3891(3) 0.1692(3) 0.0214(6) Uani 1 1 d . . . C8 C 0.04675(15) 0.3691(3) 0.2338(3) 0.0200(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O4 0.0130(10) 0.0374(11) 0.0355(12) -0.0051(9) -0.0024(8) -0.0047(8) C1 0.0192(15) 0.0275(14) 0.0270(16) 0.0004(12) 0.0005(12) -0.0009(12) O3 0.0147(9) 0.0221(9) 0.0200(9) 0.0023(8) -0.0014(7) -0.0037(7) Co1 0.0140(3) 0.0219(3) 0.0150(3) 0.000 -0.00061(18) 0.000 O1 0.0305(11) 0.0277(10) 0.0165(10) -0.0018(8) 0.0007(8) -0.0078(9) C3 0.0166(14) 0.0204(13) 0.0169(13) 0.0018(11) -0.0017(10) -0.0017(11) C4 0.0187(14) 0.0268(14) 0.0199(14) -0.0014(12) 0.0026(11) -0.0003(11) O5 0.0224(11) 0.0776(16) 0.0281(12) -0.0136(12) 0.0058(9) -0.0059(11) C6 0.0186(15) 0.0394(18) 0.0308(17) -0.0113(13) -0.0002(12) -0.0066(13) C2 0.0132(12) 0.0207(12) 0.0221(14) -0.0013(11) -0.0015(10) 0.0048(11) C7 0.0240(16) 0.0359(17) 0.0288(16) -0.0143(13) 0.0051(13) -0.0010(13) C5 0.0151(13) 0.0253(14) 0.0239(15) -0.0012(12) -0.0001(11) -0.0022(11) C8 0.0144(14) 0.0232(13) 0.0226(14) 0.0035(12) 0.0018(10) -0.0007(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O4 C1 1.222(3) . ? O4 Co1 2.1605(18) 2 ? C1 O5 1.296(3) . ? C1 C5 1.490(4) . ? O3 C2 1.275(3) . ? O3 Co1 2.0767(17) 5 ? Co1 O1 2.0646(18) . ? Co1 O1 2.0646(18) 3_554 ? Co1 O3 2.0767(17) 7 ? Co1 O3 2.0767(17) 5 ? Co1 O4 2.1605(18) 2_554 ? Co1 O4 2.1605(18) 4_455 ? O1 C2 1.244(3) . ? C3 C4 1.381(3) . ? C3 C8 1.395(3) . ? C3 C2 1.497(3) . ? C4 C5 1.392(3) . ? C4 H4A 0.9300 . ? C6 C7 1.377(4) . ? C6 C5 1.377(4) . ? C6 H6A 0.9300 . ? C7 C8 1.372(4) . ? C7 H7A 0.9300 . ? C8 C8 1.497(5) 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 O4 Co1 140.10(19) . 2 ? O4 C1 O5 124.2(3) . . ? O4 C1 C5 122.8(3) . . ? O5 C1 C5 113.0(2) . . ? C2 O3 Co1 129.69(16) . 5 ? O1 Co1 O1 92.21(10) . 3_554 ? O1 Co1 O3 176.90(7) . 7 ? O1 Co1 O3 87.85(7) 3_554 7 ? O1 Co1 O3 87.85(7) . 5 ? O1 Co1 O3 176.90(7) 3_554 5 ? O3 Co1 O3 92.26(9) 7 5 ? O1 Co1 O4 83.17(7) . 2_554 ? O1 Co1 O4 97.62(7) 3_554 2_554 ? O3 Co1 O4 93.75(7) 7 2_554 ? O3 Co1 O4 85.46(7) 5 2_554 ? O1 Co1 O4 97.62(7) . 4_455 ? O1 Co1 O4 83.17(7) 3_554 4_455 ? O3 Co1 O4 85.46(7) 7 4_455 ? O3 Co1 O4 93.75(7) 5 4_455 ? O4 Co1 O4 178.86(10) 2_554 4_455 ? C2 O1 Co1 128.54(17) . . ? C4 C3 C8 120.4(2) . . ? C4 C3 C2 118.4(2) . . ? C8 C3 C2 121.1(2) . . ? C3 C4 C5 119.9(2) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C7 C6 C5 120.2(3) . . ? C7 C6 H6A 119.9 . . ? C5 C6 H6A 119.9 . . ? O1 C2 O3 124.4(2) . . ? O1 C2 C3 118.6(2) . . ? O3 C2 C3 116.9(2) . . ? C8 C7 C6 121.3(3) . . ? C8 C7 H7A 119.3 . . ? C6 C7 H7A 119.3 . . ? C6 C5 C4 119.4(2) . . ? C6 C5 C1 120.7(2) . . ? C4 C5 C1 119.9(2) . . ? C7 C8 C3 118.7(2) . . ? C7 C8 C8 119.2(2) . 3 ? C3 C8 C8 122.0(2) . 3 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.524 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.071 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 759543' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H8 Mn O8' _chemical_formula_sum 'C16 H8 Mn O8' _chemical_formula_weight 383.16 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbcn ' _symmetry_space_group_name_Hall '-P 2n 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 15.764(3) _cell_length_b 9.1079(15) _cell_length_c 9.7436(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1398.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 934 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 22.82 _exptl_crystal_description block _exptl_crystal_colour pink _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.819 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.992 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 0.78 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7859 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_sigmaI/netI 0.0649 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.00 _reflns_number_total 1672 _reflns_number_gt 1254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0359P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1672 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0812 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0961 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.07822(17) 0.7016(3) 0.8826(3) 0.0209(7) Uani 1 1 d . . . C2 C 0.16313(17) 0.6889(4) 0.9167(3) 0.0235(7) Uani 1 1 d . . . H2A H 0.1842 0.7355 0.9982 0.028 Uiso 1 1 d R . . C3 C 0.21804(18) 0.6085(4) 0.8344(3) 0.0242(7) Uani 1 1 d . . . C4 C 0.18637(19) 0.5401(4) 0.7185(3) 0.0316(8) Uani 1 1 d . . . H4A H 0.2240 0.4865 0.6594 0.038 Uiso 1 1 d R . . C5 C 0.1016(2) 0.5493(4) 0.6871(3) 0.0319(8) Uani 1 1 d . . . H5A H 0.0796 0.4989 0.6082 0.038 Uiso 1 1 d R . . C6 C 0.04645(17) 0.6291(3) 0.7671(3) 0.0218(7) Uani 1 1 d . . . C7 C 0.02306(17) 0.7979(3) 0.9688(3) 0.0213(7) Uani 1 1 d . . . C8 C 0.30874(19) 0.5941(4) 0.8709(3) 0.0270(8) Uani 1 1 d . . . Mn1 Mn 0.0000 1.04838(7) 0.7500 0.01894(19) Uani 1 2 d S . . O1 O 0.36241(12) 0.5463(3) 0.7936(2) 0.0336(6) Uani 1 1 d . . . O2 O 0.32439(14) 0.6352(3) 0.9970(2) 0.0461(8) Uani 1 1 d . . . O3 O 0.02990(13) 0.7911(3) 1.0965(2) 0.0303(6) Uani 1 1 d . . . O4 O -0.02789(12) 0.8828(2) 0.9052(2) 0.0218(5) Uani 1 1 d . . . H2 H 0.385(3) 0.619(5) 1.021(4) 0.080(14) 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 C1 0.0191(15) 0.0221(17) 0.0214(17) 0.0016(13) 0.0019(12) 0.0015(13) C2 0.0212(15) 0.0300(19) 0.0191(16) 0.0014(14) -0.0024(12) -0.0001(14) C3 0.0188(15) 0.0278(18) 0.0260(18) 0.0013(15) -0.0008(13) 0.0037(14) C4 0.0214(16) 0.045(2) 0.028(2) -0.0114(16) 0.0013(13) 0.0068(16) C5 0.0281(17) 0.038(2) 0.0301(19) -0.0136(17) -0.0055(14) 0.0024(17) C6 0.0183(15) 0.0251(17) 0.0219(17) 0.0034(14) 0.0000(13) -0.0001(13) C7 0.0159(14) 0.0220(17) 0.0258(18) -0.0032(14) 0.0034(12) -0.0040(12) C8 0.0212(16) 0.033(2) 0.0264(18) 0.0034(15) -0.0025(14) -0.0012(14) Mn1 0.0153(3) 0.0243(4) 0.0172(3) 0.000 0.0002(3) 0.000 O1 0.0169(11) 0.0448(16) 0.0391(14) -0.0064(12) 0.0036(10) 0.0057(11) O2 0.0200(13) 0.087(2) 0.0309(15) -0.0119(14) -0.0067(11) 0.0055(14) O3 0.0396(13) 0.0329(14) 0.0184(12) -0.0012(10) 0.0007(10) 0.0116(11) O4 0.0161(10) 0.0264(13) 0.0230(12) 0.0032(10) 0.0030(9) 0.0034(9) _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 C2 1.384(4) . ? C1 C6 1.397(4) . ? C1 C7 1.494(4) . ? C2 C3 1.388(4) . ? C2 H2A 0.9600 . ? C3 C4 1.383(4) . ? C3 C8 1.479(4) . ? C4 C5 1.374(4) . ? C4 H4A 0.9600 . ? C5 C6 1.375(4) . ? C5 H5A 0.9599 . ? C6 C6 1.502(5) 3_556 ? C7 O3 1.250(4) . ? C7 O4 1.276(3) . ? C8 O1 1.214(4) . ? C8 O2 1.308(4) . ? Mn1 O3 2.144(2) 5_577 ? Mn1 O3 2.144(2) 7_575 ? Mn1 O4 2.181(2) 3_556 ? Mn1 O4 2.181(2) . ? Mn1 O1 2.210(2) 8_665 ? Mn1 O1 2.210(2) 6_567 ? O1 Mn1 2.210(2) 6_657 ? O2 H2 0.99(4) . ? O3 Mn1 2.144(2) 5_577 ? 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 C2 C1 C6 120.0(3) . . ? C2 C1 C7 118.5(3) . . ? C6 C1 C7 121.5(2) . . ? C1 C2 C3 120.6(3) . . ? C1 C2 H2A 119.8 . . ? C3 C2 H2A 119.7 . . ? C4 C3 C2 118.9(3) . . ? C4 C3 C8 120.4(3) . . ? C2 C3 C8 120.7(3) . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4A 119.9 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5A 120.0 . . ? C6 C5 H5A 118.6 . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C6 119.4(3) . 3_556 ? C1 C6 C6 121.9(3) . 3_556 ? O3 C7 O4 124.6(3) . . ? O3 C7 C1 118.7(3) . . ? O4 C7 C1 116.6(3) . . ? O1 C8 O2 123.7(3) . . ? O1 C8 C3 123.8(3) . . ? O2 C8 C3 112.5(3) . . ? O3 Mn1 O3 94.00(12) 5_577 7_575 ? O3 Mn1 O4 178.79(8) 5_577 3_556 ? O3 Mn1 O4 86.77(8) 7_575 3_556 ? O3 Mn1 O4 86.77(8) 5_577 . ? O3 Mn1 O4 178.79(8) 7_575 . ? O4 Mn1 O4 92.47(11) 3_556 . ? O3 Mn1 O1 95.03(8) 5_577 8_665 ? O3 Mn1 O1 85.65(8) 7_575 8_665 ? O4 Mn1 O1 85.95(8) 3_556 8_665 ? O4 Mn1 O1 93.36(8) . 8_665 ? O3 Mn1 O1 85.65(8) 5_577 6_567 ? O3 Mn1 O1 95.03(8) 7_575 6_567 ? O4 Mn1 O1 93.36(8) 3_556 6_567 ? O4 Mn1 O1 85.95(8) . 6_567 ? O1 Mn1 O1 179.01(13) 8_665 6_567 ? C8 O1 Mn1 143.2(2) . 6_657 ? C8 O2 H2 111(2) . . ? C7 O3 Mn1 129.9(2) . 5_577 ? C7 O4 Mn1 129.01(18) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.574 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.079 # Attachment '3.cif' data_90721cm _database_code_depnum_ccdc_archive 'CCDC 759544' #TrackingRef '3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H11 Cd N2 O4, H2 O' _chemical_formula_sum 'C20 H13 Cd N2 O5' _chemical_formula_weight 473.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2/n ' _symmetry_space_group_name_Hall '-P 2yac ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 10.642(2) _cell_length_b 10.768(2) _cell_length_c 14.943(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.763(2) _cell_angle_gamma 90.00 _cell_volume 1711.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3139 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 26.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.838 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 1.313 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.74 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10259 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3013 _reflns_number_gt 2495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0173P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3013 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0311 _refine_ls_wR_factor_ref 0.0618 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6177(4) 0.8446(4) 0.6728(3) 0.0547(12) Uani 1 1 d . . . H3 H 0.6885 0.7974 0.6877 0.066 Uiso 1 1 calc R . . C2 C 0.5854(4) 0.9402(4) 0.7296(3) 0.0709(15) Uani 1 1 d . . . H1 H 0.6336 0.9555 0.7814 0.085 Uiso 1 1 calc R . . C3 C 0.4840(4) 1.0108(4) 0.7097(3) 0.0593(12) Uani 1 1 d . . . H2 H 0.4629 1.0766 0.7466 0.071 Uiso 1 1 calc R . . C4 C 0.4498(3) 0.8855(3) 0.5789(2) 0.0324(9) Uani 1 1 d . . . C5 C 0.4108(4) 0.9843(3) 0.6327(3) 0.0418(10) Uani 1 1 d . . . C6 C 0.2989(4) 1.0503(4) 0.6092(3) 0.0546(12) Uani 1 1 d . . . H4 H 0.2755 1.1182 0.6433 0.066 Uiso 1 1 calc R . . C7 C 0.2263(4) 1.0156(4) 0.5381(3) 0.0541(12) Uani 1 1 d . . . H5 H 0.1534 1.0601 0.5239 0.065 Uiso 1 1 calc R . . C8 C 0.2588(3) 0.9124(4) 0.4842(2) 0.0371(9) Uani 1 1 d . . . C9 C 0.3729(3) 0.8498(3) 0.5014(2) 0.0310(8) Uani 1 1 d . . . C10 C 0.3349(3) 0.7120(4) 0.3868(3) 0.0417(10) Uani 1 1 d . . . H8 H 0.3605 0.6453 0.3522 0.050 Uiso 1 1 calc R . . C11 C 0.2182(4) 0.7654(4) 0.3679(3) 0.0489(11) Uani 1 1 d . . . H7 H 0.1659 0.7327 0.3227 0.059 Uiso 1 1 calc R . . C12 C 0.1808(4) 0.8648(4) 0.4153(3) 0.0485(11) Uani 1 1 d . . . H6 H 0.1033 0.9015 0.4022 0.058 Uiso 1 1 calc R . . C13 C 0.8291(3) 0.6263(3) 0.5843(2) 0.0289(8) Uani 1 1 d . . . C14 C 1.0610(3) 0.6681(3) 0.5960(2) 0.0403(10) Uani 1 1 d . . . H10 H 1.0555 0.7047 0.5397 0.048 Uiso 1 1 calc R . . C15 C 0.9552(3) 0.6183(3) 0.6329(2) 0.0279(8) Uani 1 1 d . . . C16 C 0.9659(3) 0.5616(3) 0.7160(2) 0.0278(8) Uani 1 1 d . . . H9 H 0.8950 0.5279 0.7414 0.033 Uiso 1 1 calc R . . C17 C 1.0810(3) 0.5544(3) 0.7616(2) 0.0252(8) Uani 1 1 d . . . C18 C 1.1880(3) 0.6075(3) 0.7250(2) 0.0277(8) Uani 1 1 d . . . C19 C 1.1750(3) 0.6642(3) 0.6422(2) 0.0398(10) Uani 1 1 d . . . H11 H 1.2449 0.7005 0.6171 0.048 Uiso 1 1 calc R . . C20 C 1.0923(3) 0.4811(4) 0.8467(2) 0.0287(8) Uani 1 1 d . . . Cd1 Cd 0.59716(2) 0.64933(2) 0.505925(16) 0.02903(10) Uani 1 1 d . . . N1 N 0.4113(3) 0.7527(3) 0.45243(19) 0.0320(7) Uani 1 1 d . . . N2 N 0.5530(3) 0.8170(3) 0.5985(2) 0.0363(8) Uani 1 1 d . . . O1 O 0.9145(2) 0.7404(2) 0.33347(18) 0.0540(8) Uani 1 1 d . . . H1D H 0.8736 0.7549 0.3803 0.065 Uiso 1 1 d R . . H1A H 0.9094 0.6636 0.3207 0.081 Uiso 1 1 d R . . O2 O 0.7369(2) 0.5720(2) 0.61713(16) 0.0408(7) Uani 1 1 d . . . O3 O 0.8183(2) 0.6889(2) 0.51390(16) 0.0426(7) Uani 1 1 d . . . O4 O 1.0557(2) 0.5266(2) 0.91899(14) 0.0354(6) Uani 1 1 d . . . O5 O 1.1350(2) 0.3737(2) 0.84285(16) 0.0442(7) 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 0.048(3) 0.064(3) 0.052(3) -0.021(2) -0.017(2) 0.012(2) C2 0.066(3) 0.082(4) 0.064(3) -0.045(3) -0.023(3) 0.016(3) C3 0.061(3) 0.055(3) 0.063(3) -0.026(3) 0.005(2) 0.005(2) C4 0.034(2) 0.029(2) 0.034(2) 0.0015(17) 0.0031(17) -0.0022(17) C5 0.044(2) 0.036(2) 0.046(3) -0.006(2) 0.0045(19) 0.0037(19) C6 0.062(3) 0.041(3) 0.062(3) -0.008(2) 0.011(2) 0.015(2) C7 0.046(3) 0.051(3) 0.066(3) 0.008(2) 0.009(2) 0.024(2) C8 0.035(2) 0.041(2) 0.035(2) 0.0118(19) 0.0027(17) 0.0076(18) C9 0.029(2) 0.032(2) 0.033(2) 0.0079(18) 0.0039(16) 0.0016(17) C10 0.043(2) 0.047(2) 0.035(2) -0.001(2) -0.0056(18) 0.001(2) C11 0.039(2) 0.069(3) 0.038(2) 0.009(2) -0.0151(19) -0.002(2) C12 0.038(2) 0.062(3) 0.046(3) 0.021(2) -0.0033(19) 0.014(2) C13 0.0269(19) 0.036(2) 0.0232(19) -0.0028(17) -0.0043(15) 0.0033(17) C14 0.032(2) 0.061(3) 0.028(2) 0.0193(19) -0.0018(16) -0.0028(19) C15 0.0236(18) 0.034(2) 0.0254(19) 0.0036(16) -0.0052(14) 0.0008(15) C16 0.0181(17) 0.038(2) 0.0271(19) 0.0042(17) 0.0016(14) -0.0016(15) C17 0.0238(18) 0.031(2) 0.0205(18) -0.0007(16) -0.0017(14) 0.0010(15) C18 0.0194(18) 0.039(2) 0.0246(19) -0.0039(16) -0.0022(14) 0.0028(15) C19 0.0225(19) 0.059(3) 0.038(2) 0.020(2) 0.0016(16) -0.0064(18) C20 0.0145(17) 0.044(2) 0.027(2) 0.0049(18) -0.0044(14) -0.0012(16) Cd1 0.02526(15) 0.03495(17) 0.02637(15) -0.00431(13) -0.00770(10) 0.00241(13) N1 0.0303(17) 0.0343(18) 0.0310(17) 0.0016(15) -0.0041(13) -0.0007(14) N2 0.0320(18) 0.0382(19) 0.0383(19) -0.0075(15) -0.0059(14) 0.0002(14) O1 0.0507(18) 0.0468(17) 0.0653(19) -0.0039(15) 0.0121(15) 0.0010(14) O2 0.0246(14) 0.0549(17) 0.0423(16) 0.0127(14) -0.0087(12) -0.0057(12) O3 0.0306(15) 0.0638(18) 0.0326(15) 0.0151(14) -0.0096(11) 0.0024(13) O4 0.0372(15) 0.0495(16) 0.0197(13) 0.0032(12) 0.0021(11) 0.0039(12) O5 0.0524(17) 0.0469(17) 0.0332(15) 0.0086(13) -0.0013(12) 0.0173(14) _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 N2 1.322(4) . ? C1 C2 1.384(5) . ? C1 H3 0.9300 . ? C2 C3 1.346(5) . ? C2 H1 0.9300 . ? C3 C5 1.399(5) . ? C3 H2 0.9300 . ? C4 N2 1.348(4) . ? C4 C5 1.404(5) . ? C4 C9 1.449(5) . ? C5 C6 1.422(5) . ? C6 C7 1.348(5) . ? C6 H4 0.9300 . ? C7 C8 1.422(5) . ? C7 H5 0.9300 . ? C8 C12 1.400(5) . ? C8 C9 1.406(5) . ? C9 N1 1.347(4) . ? C10 N1 1.329(4) . ? C10 C11 1.391(5) . ? C10 H8 0.9300 . ? C11 C12 1.350(5) . ? C11 H7 0.9300 . ? C12 H6 0.9300 . ? C13 O3 1.251(4) . ? C13 O2 1.255(4) . ? C13 C15 1.509(4) . ? C13 Cd1 2.711(3) . ? C14 C15 1.378(5) . ? C14 C19 1.378(4) . ? C14 H10 0.9300 . ? C15 C16 1.385(4) . ? C16 C17 1.385(4) . ? C16 H9 0.9300 . ? C17 C18 1.401(4) . ? C17 C20 1.499(4) . ? C18 C19 1.382(5) . ? C18 C18 1.496(6) 2_756 ? C19 H11 0.9300 . ? C20 O5 1.244(4) . ? C20 O4 1.260(4) . ? Cd1 N2 2.331(3) . ? Cd1 O4 2.332(2) 4_565 ? Cd1 O2 2.348(2) . ? Cd1 N1 2.386(3) . ? Cd1 O3 2.391(2) . ? Cd1 O4 2.401(2) 2_656 ? Cd1 O5 2.494(3) 4_565 ? O1 H1D 0.8500 . ? O1 H1A 0.8500 . ? O4 Cd1 2.332(2) 4_666 ? O4 Cd1 2.401(2) 2_656 ? O5 Cd1 2.494(3) 4_666 ? 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 N2 C1 C2 123.3(4) . . ? N2 C1 H3 118.3 . . ? C2 C1 H3 118.3 . . ? C3 C2 C1 119.8(4) . . ? C3 C2 H1 120.1 . . ? C1 C2 H1 120.1 . . ? C2 C3 C5 119.3(4) . . ? C2 C3 H2 120.3 . . ? C5 C3 H2 120.3 . . ? N2 C4 C5 122.9(3) . . ? N2 C4 C9 117.7(3) . . ? C5 C4 C9 119.3(3) . . ? C3 C5 C4 117.3(4) . . ? C3 C5 C6 122.8(4) . . ? C4 C5 C6 119.8(4) . . ? C7 C6 C5 120.8(4) . . ? C7 C6 H4 119.6 . . ? C5 C6 H4 119.6 . . ? C6 C7 C8 121.3(4) . . ? C6 C7 H5 119.3 . . ? C8 C7 H5 119.3 . . ? C12 C8 C9 116.6(4) . . ? C12 C8 C7 123.6(4) . . ? C9 C8 C7 119.7(4) . . ? N1 C9 C8 123.2(3) . . ? N1 C9 C4 117.8(3) . . ? C8 C9 C4 118.8(3) . . ? N1 C10 C11 122.4(4) . . ? N1 C10 H8 118.8 . . ? C11 C10 H8 118.8 . . ? C12 C11 C10 119.8(4) . . ? C12 C11 H7 120.1 . . ? C10 C11 H7 120.1 . . ? C11 C12 C8 119.9(4) . . ? C11 C12 H6 120.0 . . ? C8 C12 H6 120.0 . . ? O3 C13 O2 121.8(3) . . ? O3 C13 C15 119.5(3) . . ? O2 C13 C15 118.6(3) . . ? O3 C13 Cd1 61.89(17) . . ? O2 C13 Cd1 59.95(17) . . ? C15 C13 Cd1 176.3(2) . . ? C15 C14 C19 120.4(3) . . ? C15 C14 H10 119.8 . . ? C19 C14 H10 119.8 . . ? C14 C15 C16 119.0(3) . . ? C14 C15 C13 120.7(3) . . ? C16 C15 C13 120.3(3) . . ? C15 C16 C17 120.8(3) . . ? C15 C16 H9 119.6 . . ? C17 C16 H9 119.6 . . ? C16 C17 C18 120.2(3) . . ? C16 C17 C20 119.6(3) . . ? C18 C17 C20 120.1(3) . . ? C19 C18 C17 118.0(3) . . ? C19 C18 C18 120.7(3) . 2_756 ? C17 C18 C18 121.3(3) . 2_756 ? C14 C19 C18 121.6(3) . . ? C14 C19 H11 119.2 . . ? C18 C19 H11 119.2 . . ? O5 C20 O4 121.6(3) . . ? O5 C20 C17 118.1(3) . . ? O4 C20 C17 120.3(3) . . ? N2 Cd1 O4 157.20(9) . 4_565 ? N2 Cd1 O2 89.40(10) . . ? O4 Cd1 O2 102.18(9) 4_565 . ? N2 Cd1 N1 69.98(10) . . ? O4 Cd1 N1 92.95(9) 4_565 . ? O2 Cd1 N1 154.55(9) . . ? N2 Cd1 O3 92.77(9) . . ? O4 Cd1 O3 109.98(8) 4_565 . ? O2 Cd1 O3 55.03(8) . . ? N1 Cd1 O3 137.58(9) . . ? N2 Cd1 O4 89.84(9) . 2_656 ? O4 Cd1 O4 72.17(9) 4_565 2_656 ? O2 Cd1 O4 84.12(8) . 2_656 ? N1 Cd1 O4 81.18(9) . 2_656 ? O3 Cd1 O4 139.00(8) . 2_656 ? N2 Cd1 O5 134.29(10) . 4_565 ? O4 Cd1 O5 53.72(8) 4_565 4_565 ? O2 Cd1 O5 122.57(9) . 4_565 ? N1 Cd1 O5 82.88(9) . 4_565 ? O3 Cd1 O5 83.01(8) . 4_565 ? O4 Cd1 O5 122.26(8) 2_656 4_565 ? N2 Cd1 C13 90.69(10) . . ? O4 Cd1 C13 108.69(9) 4_565 . ? O2 Cd1 C13 27.56(9) . . ? N1 Cd1 C13 157.22(10) . . ? O3 Cd1 C13 27.49(9) . . ? O4 Cd1 C13 111.65(10) 2_656 . ? O5 Cd1 C13 103.92(9) 4_565 . ? C10 N1 C9 117.9(3) . . ? C10 N1 Cd1 125.1(3) . . ? C9 N1 Cd1 116.3(2) . . ? C1 N2 C4 117.4(3) . . ? C1 N2 Cd1 124.3(3) . . ? C4 N2 Cd1 118.2(2) . . ? H1D O1 H1A 109.5 . . ? C13 O2 Cd1 92.5(2) . . ? C13 O3 Cd1 90.6(2) . . ? C20 O4 Cd1 95.9(2) . 4_666 ? C20 O4 Cd1 147.9(2) . 2_656 ? Cd1 O4 Cd1 107.83(9) 4_666 2_656 ? C20 O5 Cd1 88.7(2) . 4_666 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.771 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.082 # Attachment '4.cif' data_80611dm _database_code_depnum_ccdc_archive 'CCDC 759545' #TrackingRef '4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H23 Cl3 Eu2 N2 O14' _chemical_formula_sum 'C30 H23 Cl3 Eu2 N2 O14' _chemical_formula_weight 1045.77 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.432(5) _cell_length_b 22.089(8) _cell_length_c 11.142(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.807(6) _cell_angle_gamma 90.00 _cell_volume 3552(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 972 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 27.80 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.956 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 3.794 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.38 _exptl_absorpt_correction_T_max 0.43 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8707 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3135 _reflns_number_gt 2861 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.15P)^2^+1.99P] 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 3135 _refine_ls_number_parameters 192 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0683 _refine_ls_wR_factor_ref 0.2122 _refine_ls_wR_factor_gt 0.2067 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.170 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6902(6) 0.1600(5) 0.6499(8) 0.037(2) Uani 1 1 d . . . C2 C 0.7800(6) 0.1768(4) 0.6868(7) 0.0238(17) Uani 1 1 d . . . C3 C 0.8461(5) 0.1872(4) 0.6007(7) 0.0191(15) Uani 1 1 d . . . H3 H 0.9058 0.1980 0.6246 0.023 Uiso 1 1 calc R . . C4 C 0.8251(6) 0.1821(4) 0.4789(7) 0.0220(16) Uani 1 1 d . . . C5 C 0.7351(6) 0.1667(4) 0.4430(7) 0.031(2) Uani 1 1 d . . . H5 H 0.7193 0.1655 0.3619 0.038 Uiso 1 1 calc R . . C6 C 0.6689(6) 0.1531(5) 0.5290(8) 0.040(2) Uani 1 1 d . . . H6 H 0.6105 0.1395 0.5052 0.048 Uiso 1 1 calc R . . C7 C 0.8969(6) 0.1965(4) 0.3880(8) 0.0211(19) Uani 1 1 d . . . C8 C 0.8051(7) 0.1855(5) 0.8164(8) 0.032 Uani 1 1 d . . . C9 C 1.1281(6) 0.3356(4) 0.6027(8) 0.030(2) Uani 1 1 d . . . C10 C 1.0614(9) 0.3719(5) 0.6773(11) 0.054 Uani 1 1 d . B . C11 C 1.0624(9) 0.4329(5) 0.6782(12) 0.059 Uani 1 1 d . . . H11A H 1.1049 0.4548 0.6290 0.070 Uiso 0.50 1 d PR A 1 C12 C 1.0000 0.4657(6) 0.7500 0.046 Uani 1 2 d S . . H12 H 1.0000 0.5078 0.7500 0.055 Uiso 1 2 calc SR . . C13 C 1.0000 0.3414(5) 0.7500 0.026(2) Uani 1 2 d S . . H10 H 1.0000 0.2992 0.7500 0.031 Uiso 1 2 calc SR B . C14 C 1.1408(9) 0.0664(6) 0.3131(12) 0.061 Uani 1 1 d U . . H14 H 1.1689 0.0907 0.2558 0.073 Uiso 1 1 calc R . . C15 C 1.0978(10) -0.0292(6) 0.3779(12) 0.065 Uani 1 1 d . . . H30A H 1.0542 -0.0053 0.4217 0.078 Uiso 1 1 calc R . . H30B H 1.1416 -0.0472 0.4328 0.078 Uiso 1 1 calc R . . H30C H 1.0655 -0.0605 0.3346 0.078 Uiso 1 1 calc R . . C16 C 1.1950(9) -0.0163(5) 0.1980(12) 0.060 Uani 1 1 d . . . H31A H 1.1564 -0.0453 0.1571 0.072 Uiso 1 1 calc R . . H31B H 1.2498 -0.0361 0.2281 0.072 Uiso 1 1 calc R . . H31C H 1.2120 0.0152 0.1433 0.072 Uiso 1 1 calc R . . Cl1 Cl 0.6083(2) 0.14085(19) 0.7530(3) 0.0672(10) Uani 1 1 d . . . Cl2 Cl 1.1151(6) 0.4732(3) 0.5576(7) 0.082(2) Uani 0.50 1 d P B 2 Eu1 Eu 1.13951(3) 0.20417(2) 0.43003(3) 0.0275(3) Uani 1 1 d . . . N1 N 1.1461(9) 0.0089(5) 0.2945(12) 0.079 Uani 1 1 d . . . O1 O 0.8788(5) 0.1635(3) 0.8576(5) 0.0377(16) Uani 1 1 d . . . O2 O 0.7533(4) 0.2175(3) 0.8837(5) 0.0277(13) Uani 1 1 d . . . O3 O 0.9761(5) 0.2032(3) 0.4226(6) 0.0380(18) Uani 1 1 d . . . O4 O 0.8688(5) 0.1999(3) 0.2792(6) 0.0381(18) Uani 1 1 d . . . O5 O 1.0919(5) 0.2940(3) 0.5413(7) 0.0353(18) Uani 1 1 d . . . O6 O 1.2115(4) 0.3490(3) 0.6073(6) 0.0357(15) Uani 1 1 d . . . O7 O 1.1040(6) 0.0936(3) 0.3954(7) 0.0528(18) Uani 1 1 d U . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(5) 0.071(6) 0.016(4) 0.002(4) 0.007(3) -0.014(4) C2 0.027(4) 0.036(4) 0.009(4) 0.000(3) 0.006(3) -0.001(4) C3 0.009(4) 0.032(4) 0.017(4) 0.004(3) -0.001(3) -0.004(3) C4 0.021(4) 0.039(4) 0.007(4) -0.003(3) 0.002(3) 0.005(4) C5 0.027(5) 0.056(6) 0.011(4) -0.005(4) -0.001(3) -0.011(4) C6 0.020(5) 0.077(7) 0.023(5) -0.004(4) 0.005(4) -0.016(5) C7 0.022(5) 0.033(4) 0.008(4) -0.003(3) 0.006(3) 0.000(3) C8 0.028 0.044 0.024 0.002 0.007 -0.002 C9 0.023(5) 0.048(5) 0.019(4) 0.007(4) 0.010(4) 0.009(4) C10 0.059 0.053 0.051 0.002 0.014 0.000 C11 0.070 0.044 0.064 0.006 0.028 0.003 C12 0.052 0.023 0.062 0.000 0.026 0.000 C13 0.017(6) 0.031(6) 0.030(6) 0.000 0.008(5) 0.000 C14 0.066 0.058 0.059 -0.015 0.011 -0.008 C15 0.073 0.066 0.056 -0.028 0.014 0.013 C16 0.061 0.054 0.066 0.016 0.014 0.029 Cl1 0.0381(15) 0.130(3) 0.0336(15) -0.0013(16) 0.0183(12) -0.0366(18) Cl2 0.089(5) 0.058(3) 0.100(5) 0.041(4) 0.064(4) 0.016(3) Eu1 0.0198(4) 0.0503(4) 0.0126(4) -0.00404(15) 0.0017(2) -0.00235(16) N1 0.098 0.054 0.085 0.002 0.026 0.007 O1 0.036(4) 0.059(4) 0.018(3) -0.006(3) -0.005(3) 0.009(3) O2 0.022(3) 0.052(3) 0.009(3) -0.001(2) 0.001(2) -0.001(3) O3 0.020(4) 0.077(5) 0.017(4) -0.006(3) 0.000(3) -0.005(3) O4 0.028(4) 0.074(5) 0.012(3) 0.007(3) 0.001(3) -0.009(3) O5 0.022(4) 0.054(4) 0.030(4) -0.015(3) 0.001(3) -0.003(3) O6 0.020(3) 0.050(4) 0.037(4) -0.011(3) 0.003(3) 0.003(3) O7 0.050(5) 0.052(4) 0.057(4) -0.011(3) 0.005(3) -0.005(4) _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 C6 1.386(12) . ? C1 C2 1.404(12) . ? C1 Cl1 1.713(8) . ? C2 C3 1.382(11) . ? C2 C8 1.497(12) . ? C3 C4 1.391(11) . ? C3 H3 0.9300 . ? C4 C5 1.395(12) . ? C4 C7 1.493(11) . ? C5 C6 1.395(12) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 O3 1.210(12) . ? C7 O4 1.276(12) . ? C8 O1 1.252(12) . ? C8 O2 1.278(11) . ? C8 Eu1 2.954(10) 2_756 ? C9 O6 1.239(11) . ? C9 O5 1.255(12) . ? C9 C10 1.511(14) . ? C10 C11 1.348(15) . ? C10 C13 1.385(12) . ? C11 C12 1.412(13) . ? C11 Cl2 1.791(12) . ? C11 H11A 0.9600 . ? C12 C11 1.412(13) 2_756 ? C12 H12 0.9300 . ? C13 C10 1.385(12) 2_756 ? C13 H10 0.9300 . ? C14 O7 1.223(13) . ? C14 N1 1.289(16) . ? C14 H14 0.9300 . ? C15 N1 1.440(17) . ? C15 H30A 0.9600 . ? C15 H30B 0.9600 . ? C15 H30C 0.9600 . ? C16 N1 1.410(16) . ? C16 H31A 0.9600 . ? C16 H31B 0.9600 . ? C16 H31C 0.9600 . ? Cl2 H11A 0.9065 . ? Eu1 O4 2.334(7) 2_755 ? Eu1 O3 2.359(7) . ? Eu1 O5 2.443(6) . ? Eu1 O2 2.446(6) 8 ? Eu1 O6 2.490(6) 7_756 ? Eu1 O7 2.524(7) . ? Eu1 O1 2.548(6) 2_756 ? Eu1 O2 2.587(6) 2_756 ? Eu1 C8 2.954(10) 2_756 ? O1 Eu1 2.548(6) 2_756 ? O2 Eu1 2.446(6) 8_456 ? O2 Eu1 2.587(6) 2_756 ? O4 Eu1 2.334(7) 2_755 ? O6 Eu1 2.490(6) 7_756 ? 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 C6 C1 C2 120.3(8) . . ? C6 C1 Cl1 118.6(7) . . ? C2 C1 Cl1 120.8(6) . . ? C3 C2 C1 118.9(7) . . ? C3 C2 C8 119.3(8) . . ? C1 C2 C8 121.8(7) . . ? C2 C3 C4 121.4(7) . . ? C2 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 119.2(7) . . ? C3 C4 C7 120.0(8) . . ? C5 C4 C7 120.6(7) . . ? C6 C5 C4 120.0(7) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C1 C6 C5 119.9(8) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? O3 C7 O4 125.6(8) . . ? O3 C7 C4 118.1(8) . . ? O4 C7 C4 116.3(8) . . ? O1 C8 O2 120.1(9) . . ? O1 C8 C2 119.7(8) . . ? O2 C8 C2 120.1(8) . . ? O1 C8 Eu1 59.1(5) . 2_756 ? O2 C8 Eu1 61.0(5) . 2_756 ? C2 C8 Eu1 178.2(6) . 2_756 ? O6 C9 O5 126.5(8) . . ? O6 C9 C10 118.4(9) . . ? O5 C9 C10 115.1(8) . . ? C11 C10 C13 119.3(11) . . ? C11 C10 C9 121.9(10) . . ? C13 C10 C9 118.8(10) . . ? C10 C11 C12 120.7(11) . . ? C10 C11 Cl2 119.7(10) . . ? C12 C11 Cl2 116.8(9) . . ? C10 C11 H11A 120.5 . . ? C12 C11 H11A 118.8 . . ? Cl2 C11 H11A 15.9 . . ? C11 C12 C11 118.3(13) 2_756 . ? C11 C12 H12 120.8 2_756 . ? C11 C12 H12 120.8 . . ? C10 C13 C10 121.7(13) . 2_756 ? C10 C13 H10 119.1 . . ? C10 C13 H10 119.1 2_756 . ? O7 C14 N1 129.1(13) . . ? O7 C14 H14 115.4 . . ? N1 C14 H14 115.4 . . ? N1 C15 H30A 109.5 . . ? N1 C15 H30B 109.5 . . ? H30A C15 H30B 109.5 . . ? N1 C15 H30C 109.5 . . ? H30A C15 H30C 109.5 . . ? H30B C15 H30C 109.5 . . ? N1 C16 H31A 109.5 . . ? N1 C16 H31B 109.5 . . ? H31A C16 H31B 109.5 . . ? N1 C16 H31C 109.5 . . ? H31A C16 H31C 109.5 . . ? H31B C16 H31C 109.5 . . ? C11 Cl2 H11A 16.9 . . ? O4 Eu1 O3 85.9(2) 2_755 . ? O4 Eu1 O5 121.9(3) 2_755 . ? O3 Eu1 O5 74.8(2) . . ? O4 Eu1 O2 81.0(2) 2_755 8 ? O3 Eu1 O2 132.3(2) . 8 ? O5 Eu1 O2 74.2(2) . 8 ? O4 Eu1 O6 81.1(2) 2_755 7_756 ? O3 Eu1 O6 148.8(2) . 7_756 ? O5 Eu1 O6 135.8(2) . 7_756 ? O2 Eu1 O6 73.4(2) 8 7_756 ? O4 Eu1 O7 78.5(3) 2_755 . ? O3 Eu1 O7 77.6(2) . . ? O5 Eu1 O7 143.7(2) . . ? O2 Eu1 O7 142.0(2) 8 . ? O6 Eu1 O7 72.1(2) 7_756 . ? O4 Eu1 O1 155.3(2) 2_755 2_756 ? O3 Eu1 O1 85.0(2) . 2_756 ? O5 Eu1 O1 77.4(2) . 2_756 ? O2 Eu1 O1 121.6(2) 8 2_756 ? O6 Eu1 O1 95.2(2) 7_756 2_756 ? O7 Eu1 O1 77.1(2) . 2_756 ? O4 Eu1 O2 145.8(2) 2_755 2_756 ? O3 Eu1 O2 128.0(2) . 2_756 ? O5 Eu1 O2 70.7(2) . 2_756 ? O2 Eu1 O2 72.1(2) 8 2_756 ? O6 Eu1 O2 71.3(2) 7_756 2_756 ? O7 Eu1 O2 110.5(2) . 2_756 ? O1 Eu1 O2 50.5(2) 2_756 2_756 ? O4 Eu1 C8 163.5(3) 2_755 2_756 ? O3 Eu1 C8 106.8(2) . 2_756 ? O5 Eu1 C8 72.7(3) . 2_756 ? O2 Eu1 C8 97.3(2) 8 2_756 ? O6 Eu1 C8 82.6(2) 7_756 2_756 ? O7 Eu1 C8 93.6(3) . 2_756 ? O1 Eu1 C8 24.9(2) 2_756 2_756 ? O2 Eu1 C8 25.6(2) 2_756 2_756 ? O4 Eu1 Eu1 115.57(19) 2_755 7_756 ? O3 Eu1 Eu1 142.74(16) . 7_756 ? O5 Eu1 Eu1 68.04(17) . 7_756 ? O2 Eu1 Eu1 37.23(14) 8 7_756 ? O6 Eu1 Eu1 67.95(15) 7_756 7_756 ? O7 Eu1 Eu1 134.1(2) . 7_756 ? O1 Eu1 Eu1 84.90(15) 2_756 7_756 ? O2 Eu1 Eu1 34.89(13) 2_756 7_756 ? C8 Eu1 Eu1 60.18(19) 2_756 7_756 ? C14 N1 C16 123.0(12) . . ? C14 N1 C15 116.3(11) . . ? C16 N1 C15 120.8(10) . . ? C8 O1 Eu1 96.0(5) . 2_756 ? C8 O2 Eu1 156.1(6) . 8_456 ? C8 O2 Eu1 93.4(5) . 2_756 ? Eu1 O2 Eu1 107.9(2) 8_456 2_756 ? C7 O3 Eu1 162.1(6) . . ? C7 O4 Eu1 164.3(7) . 2_755 ? C9 O5 Eu1 138.9(6) . . ? C9 O6 Eu1 136.1(6) . 7_756 ? C14 O7 Eu1 120.0(8) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.579 _refine_diff_density_min -2.857 _refine_diff_density_rms 0.256 # Attachment '5.cif' data_80603cm _database_code_depnum_ccdc_archive 'CCDC 759546' #TrackingRef '5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H23 Cl3 N2 Nd2 O14 ' _chemical_formula_sum 'C30 H23 Cl3 N2 Nd2 O14' _chemical_formula_weight 1030.33 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' Nd Nd -0.1943 3.0179 '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' 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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.367(4) _cell_length_b 22.032(6) _cell_length_c 11.119(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.843(5) _cell_angle_gamma 90.00 _cell_volume 3519.2(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 979 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 27.74 _exptl_crystal_description needle _exptl_crystal_colour violet _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.945 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 3.215 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.42 _exptl_absorpt_correction_T_max 0.49 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8621 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3101 _reflns_number_gt 2907 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0629P)^2^+26.4574P] 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 3101 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 0.1942(4) 0.3136(3) 0.6827(5) 0.0345(13) Uani 1 1 d . . . C2 C 0.2193(4) 0.3229(3) 0.8128(5) 0.0314(13) Uani 1 1 d . . . C3 C 0.1538(4) 0.3121(3) 0.8996(5) 0.0287(12) Uani 1 1 d . . . H3 H 0.0936 0.3013 0.8760 0.034 Uiso 1 1 calc R . . C4 C 0.1752(4) 0.3171(3) 1.0216(5) 0.0307(12) Uani 1 1 d . . . C5 C 0.2654(4) 0.3338(3) 1.0564(5) 0.0395(15) Uani 1 1 d . . . H13 H 0.2813 0.3359 1.1377 0.047 Uiso 1 1 calc R . . C6 C 0.3313(5) 0.3474(4) 0.9707(6) 0.0489(18) Uani 1 1 d . . . H5 H 0.3901 0.3609 0.9939 0.059 Uiso 1 1 calc R . . C7 C 0.3085(5) 0.3405(4) 0.8507(6) 0.0448(16) Uani 1 1 d . . . C8 C 0.1041(4) 0.3036(3) 1.1133(5) 0.0288(13) Uani 1 1 d . . . C9 C 0.1284(4) 0.1645(3) 0.6015(5) 0.0359(14) Uani 1 1 d . . . C10 C 0.0618(4) 0.1280(3) 0.6767(6) 0.0358(14) Uani 1 1 d . B . C11 C 0.0000 0.1584(4) 0.7500 0.0306(17) Uani 1 2 d S . . H8 H 0.0000 0.2006 0.7500 0.037 Uiso 1 2 calc SR . . C12 C 0.0617(8) 0.0667(4) 0.6790(11) 0.090(4) Uani 1 1 d . . . H12A H 0.1079 0.0450 0.6347 0.108 Uiso 0.50 1 d PR A 1 C13 C 0.0000 0.0351(6) 0.7500 0.091 Uani 1 2 d S . . H10 H 0.0000 -0.0071 0.7500 0.110 Uiso 1 2 calc SR . . C14 C 0.1395(8) 0.4334(5) 0.3132(10) 0.080(3) Uani 1 1 d . . . H14 H 0.1681 0.4097 0.2552 0.096 Uiso 1 1 calc R . . C15 C 0.1004(8) 0.5319(5) 0.3790(10) 0.083 Uani 1 1 d . . . H15A H 0.0785 0.5673 0.3370 0.124 Uiso 1 1 calc R . . H15B H 0.1453 0.5437 0.4394 0.124 Uiso 1 1 calc R . . H15C H 0.0489 0.5120 0.4165 0.124 Uiso 1 1 calc R . . C16 C 0.1936(7) 0.5181(4) 0.1965(9) 0.078 Uani 1 1 d . . . H16A H 0.2477 0.5388 0.2275 0.117 Uiso 1 1 calc R . . H16B H 0.1540 0.5466 0.1550 0.117 Uiso 1 1 calc R . . H16C H 0.2125 0.4870 0.1416 0.117 Uiso 1 1 calc R . . Cl1 Cl 0.39125(15) 0.36011(14) 0.74630(18) 0.0764(8) Uani 1 1 d . . . Cl2 Cl 0.1151(4) 0.0263(2) 0.5575(6) 0.0891(18) Uani 0.50 1 d P B 2 N1 N 0.1432(9) 0.4909(4) 0.2951(9) 0.105(3) Uani 1 1 d . . . Nd1 Nd 0.13972(2) 0.295564(15) 0.43016(2) 0.02955(16) Uani 1 1 d . . . O1 O 0.1205(3) 0.3367(2) 0.6411(4) 0.0450(12) Uani 1 1 d . . . O2 O 0.2474(3) 0.2819(2) 0.6170(4) 0.0357(10) Uani 1 1 d . . . O3 O 0.0227(3) 0.2958(2) 1.0785(4) 0.0473(13) Uani 1 1 d . . . O4 O 0.1312(3) 0.2992(2) 1.2206(4) 0.0478(13) Uani 1 1 d . . . O5 O 0.0921(3) 0.2063(2) 0.5400(5) 0.0424(12) Uani 1 1 d . . . O6 O 0.2122(3) 0.1510(2) 0.6072(4) 0.0445(11) Uani 1 1 d . . . O7 O 0.1041(4) 0.4051(3) 0.3951(6) 0.0632(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 0.037(3) 0.048(3) 0.019(3) 0.000(3) 0.004(3) -0.002(3) C2 0.032(3) 0.042(3) 0.020(3) 0.001(2) 0.002(2) -0.002(3) C3 0.026(3) 0.042(3) 0.019(3) 0.001(2) -0.004(2) -0.003(2) C4 0.031(3) 0.045(3) 0.016(3) -0.002(2) -0.001(2) -0.001(3) C5 0.033(3) 0.065(4) 0.020(3) -0.003(3) -0.003(2) -0.007(3) C6 0.031(3) 0.087(6) 0.029(3) -0.004(3) -0.003(3) -0.015(3) C7 0.036(3) 0.073(5) 0.026(3) 0.000(3) 0.008(3) -0.011(3) C8 0.031(3) 0.039(3) 0.016(3) -0.003(2) 0.002(2) 0.000(2) C9 0.032(3) 0.050(4) 0.026(3) -0.002(3) 0.007(3) -0.008(3) C10 0.036(3) 0.036(3) 0.036(3) -0.005(3) 0.006(3) -0.006(3) C11 0.030(4) 0.034(4) 0.028(4) 0.000 0.004(3) 0.000 C12 0.098(7) 0.047(5) 0.129(9) -0.003(5) 0.078(7) 0.004(5) C13 0.099 0.048 0.130 0.000 0.084 0.000 C14 0.105(8) 0.056(5) 0.079(7) 0.009(5) -0.002(6) 0.009(5) C15 0.092 0.070 0.086 -0.032 0.032 -0.043 C16 0.098 0.063 0.073 0.035 0.031 -0.024 Cl1 0.0507(11) 0.139(2) 0.0403(11) -0.0012(12) 0.0157(9) -0.0367(13) Cl2 0.092(3) 0.067(3) 0.109(4) -0.040(3) 0.059(3) -0.012(2) N1 0.162(10) 0.065(6) 0.089(7) 0.009(5) 0.015(7) -0.008(6) Nd1 0.0250(2) 0.0495(3) 0.0142(2) 0.00374(12) 0.00092(13) 0.00184(12) O1 0.043(3) 0.069(3) 0.023(2) -0.003(2) -0.0035(19) 0.015(2) O2 0.033(2) 0.057(3) 0.017(2) -0.0015(18) 0.0005(17) 0.004(2) O3 0.029(2) 0.088(4) 0.025(2) -0.002(2) 0.0020(19) -0.004(2) O4 0.038(3) 0.088(4) 0.016(2) 0.007(2) 0.0002(19) -0.006(2) O5 0.034(3) 0.056(3) 0.037(3) 0.014(2) 0.002(2) 0.000(2) O6 0.032(2) 0.053(3) 0.049(3) 0.013(2) 0.006(2) 0.000(2) O7 0.063(3) 0.065(4) 0.062(4) 0.012(3) 0.005(3) 0.006(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 1.257(8) . ? C1 O2 1.273(8) . ? C1 C2 1.499(8) . ? C1 Nd1 2.931(6) . ? C2 C3 1.379(8) . ? C2 C7 1.399(9) . ? C3 C4 1.391(8) . ? C3 H3 0.9300 . ? C4 C5 1.396(9) . ? C4 C8 1.484(8) . ? C5 C6 1.385(9) . ? C5 H13 0.9300 . ? C6 C7 1.377(9) . ? C6 H5 0.9300 . ? C7 Cl1 1.729(6) . ? C8 O3 1.238(8) . ? C8 O4 1.254(8) . ? C9 O6 1.241(8) . ? C9 O5 1.255(8) . ? C9 C10 1.512(8) . ? C10 C12 1.351(11) . ? C10 C11 1.387(7) . ? C11 C10 1.387(7) 2_556 ? C11 H8 0.9300 . ? C12 C13 1.383(11) . ? C12 Cl2 1.798(10) . ? C12 H12A 0.9599 . ? C13 C12 1.383(11) 2_556 ? C13 H10 0.9300 . ? C14 O7 1.221(11) . ? C14 N1 1.285(13) . ? C14 H14 0.9300 . ? C15 N1 1.442(13) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N1 1.453(12) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? Cl2 H12A 0.9588 . ? Nd1 O4 2.333(5) 1_554 ? Nd1 O3 2.335(5) 2_556 ? Nd1 O2 2.418(4) 7_556 ? Nd1 O5 2.420(4) . ? Nd1 O6 2.472(4) 7_556 ? Nd1 O7 2.496(6) . ? Nd1 O1 2.534(4) . ? Nd1 O2 2.589(4) . ? O2 Nd1 2.418(4) 7_556 ? O3 Nd1 2.335(5) 2_556 ? O4 Nd1 2.333(5) 1_556 ? O6 Nd1 2.472(4) 7_556 ? 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 121.3(6) . . ? O1 C1 C2 119.3(5) . . ? O2 C1 C2 119.4(6) . . ? O1 C1 Nd1 59.4(3) . . ? O2 C1 Nd1 61.9(3) . . ? C2 C1 Nd1 178.4(4) . . ? C3 C2 C7 117.9(5) . . ? C3 C2 C1 119.7(5) . . ? C7 C2 C1 122.4(5) . . ? C2 C3 C4 121.7(5) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 118.9(5) . . ? C3 C4 C8 120.6(5) . . ? C5 C4 C8 120.6(5) . . ? C6 C5 C4 120.5(6) . . ? C6 C5 H13 119.8 . . ? C4 C5 H13 119.8 . . ? C7 C6 C5 119.2(6) . . ? C7 C6 H5 120.4 . . ? C5 C6 H5 120.4 . . ? C6 C7 C2 121.8(6) . . ? C6 C7 Cl1 117.8(5) . . ? C2 C7 Cl1 120.2(5) . . ? O3 C8 O4 124.4(6) . . ? O3 C8 C4 118.0(5) . . ? O4 C8 C4 117.5(5) . . ? O6 C9 O5 126.7(6) . . ? O6 C9 C10 117.8(6) . . ? O5 C9 C10 115.5(5) . . ? C12 C10 C11 118.2(7) . . ? C12 C10 C9 122.9(6) . . ? C11 C10 C9 118.9(6) . . ? C10 C11 C10 122.1(8) . 2_556 ? C10 C11 H8 119.0 . . ? C10 C11 H8 119.0 2_556 . ? C10 C12 C13 120.9(8) . . ? C10 C12 Cl2 118.7(7) . . ? C13 C12 Cl2 117.7(8) . . ? C10 C12 H12A 119.1 . . ? C13 C12 H12A 119.8 . . ? Cl2 C12 H12A 20.4 . . ? C12 C13 C12 119.6(12) 2_556 . ? C12 C13 H10 120.2 2_556 . ? C12 C13 H10 120.2 . . ? O7 C14 N1 129.8(11) . . ? O7 C14 H14 115.1 . . ? N1 C14 H14 115.1 . . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C12 Cl2 H12A 20.4 . . ? C14 N1 C15 119.8(10) . . ? C14 N1 C16 123.2(11) . . ? C15 N1 C16 116.9(9) . . ? O4 Nd1 O3 85.47(17) 1_554 2_556 ? O4 Nd1 O2 80.40(16) 1_554 7_556 ? O3 Nd1 O2 131.75(17) 2_556 7_556 ? O4 Nd1 O5 121.40(18) 1_554 . ? O3 Nd1 O5 74.49(17) 2_556 . ? O2 Nd1 O5 74.37(16) 7_556 . ? O4 Nd1 O6 81.28(17) 1_554 7_556 ? O3 Nd1 O6 148.71(16) 2_556 7_556 ? O2 Nd1 O6 73.63(15) 7_556 7_556 ? O5 Nd1 O6 136.25(16) . 7_556 ? O4 Nd1 O7 78.65(19) 1_554 . ? O3 Nd1 O7 77.82(19) 2_556 . ? O2 Nd1 O7 141.77(17) 7_556 . ? O5 Nd1 O7 143.71(18) . . ? O6 Nd1 O7 71.85(18) 7_556 . ? O4 Nd1 O1 155.16(17) 1_554 . ? O3 Nd1 O1 85.13(16) 2_556 . ? O2 Nd1 O1 122.41(14) 7_556 . ? O5 Nd1 O1 77.79(17) . . ? O6 Nd1 O1 95.20(17) 7_556 . ? O7 Nd1 O1 76.91(18) . . ? O4 Nd1 O2 145.83(15) 1_554 . ? O3 Nd1 O2 128.19(15) 2_556 . ? O2 Nd1 O2 72.39(16) 7_556 . ? O5 Nd1 O2 70.77(16) . . ? O6 Nd1 O2 71.62(15) 7_556 . ? O7 Nd1 O2 110.86(18) . . ? O1 Nd1 O2 50.99(14) . . ? O4 Nd1 C1 164.08(18) 1_554 . ? O3 Nd1 C1 106.96(17) 2_556 . ? O2 Nd1 C1 97.64(16) 7_556 . ? O5 Nd1 C1 72.54(18) . . ? O6 Nd1 C1 83.01(17) 7_556 . ? O7 Nd1 C1 94.0(2) . . ? O1 Nd1 C1 25.27(16) . . ? O2 Nd1 C1 25.72(16) . . ? O4 Nd1 Nd1 115.48(13) 1_554 7_556 ? O3 Nd1 Nd1 142.60(13) 2_556 7_556 ? O2 Nd1 Nd1 37.62(10) 7_556 7_556 ? O5 Nd1 Nd1 68.16(11) . 7_556 ? O6 Nd1 Nd1 68.25(11) 7_556 7_556 ? O7 Nd1 Nd1 134.27(15) . 7_556 ? O1 Nd1 Nd1 85.27(10) . 7_556 ? O2 Nd1 Nd1 34.76(10) . 7_556 ? C1 Nd1 Nd1 60.16(13) . 7_556 ? C1 O1 Nd1 95.4(4) . . ? C1 O2 Nd1 157.1(4) . 7_556 ? C1 O2 Nd1 92.3(4) . . ? Nd1 O2 Nd1 107.61(16) 7_556 . ? C8 O3 Nd1 162.2(4) . 2_556 ? C8 O4 Nd1 164.7(4) . 1_556 ? C9 O5 Nd1 138.9(4) . . ? C9 O6 Nd1 135.6(4) . 7_556 ? C14 O7 Nd1 121.6(6) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.440 _refine_diff_density_min -2.216 _refine_diff_density_rms 0.163 # Attachment '6.cif' data_80620am _database_code_depnum_ccdc_archive 'CCDC 759547' #TrackingRef '6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H23 Cl3 N2 O14 Pr2 ' _chemical_formula_sum 'C30 H23 Cl3 N2 O14 Pr2' _chemical_formula_weight 1023.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'C2/c ' _symmetry_space_group_name_Hall '-C 2yc ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.2400(14) _cell_length_b 21.831(2) _cell_length_c 11.0019(11) _cell_angle_alpha 90.00 _cell_angle_beta 91.119(2) _cell_angle_gamma 90.00 _cell_volume 3419.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5669 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 28.21 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.988 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1992 _exptl_absorpt_coefficient_mu 3.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.46 _exptl_absorpt_correction_T_max 0.54 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart Apex CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8377 _diffrn_reflns_av_R_equivalents 0.0306 _diffrn_reflns_av_sigmaI/netI 0.0344 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3003 _reflns_number_gt 2863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0781P)^2^+39.5983P] 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 3003 _refine_ls_number_parameters 216 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1271 _refine_ls_wR_factor_gt 0.1252 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _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 -0.3076(5) 0.1581(4) 0.1481(7) 0.0443(18) Uani 1 1 d . . . C2 C -0.2188(5) 0.1764(3) 0.1873(5) 0.0322(14) Uani 1 1 d . . . C3 C -0.1529(5) 0.1882(3) 0.1011(6) 0.0296(13) Uani 1 1 d . . . H3 H -0.0925 0.1993 0.1259 0.035 Uiso 1 1 calc R . . C4 C -0.2646(5) 0.1660(3) -0.0584(6) 0.0380(16) Uani 1 1 d . . . H4 H -0.2802 0.1640 -0.1408 0.046 Uiso 1 1 calc R . . C5 C -0.3307(5) 0.1515(4) 0.0259(7) 0.0478(19) Uani 1 1 d . . . H5 H -0.3898 0.1375 0.0016 0.057 Uiso 1 1 calc R . . C6 C -0.1021(5) 0.1978(3) -0.1139(6) 0.0296(15) Uani 1 1 d . . . C7 C 0.1298(5) 0.3350(3) 0.1011(6) 0.0355(15) Uani 1 1 d . . . C8 C -0.1937(5) 0.1861(3) 0.3190(6) 0.0326(14) Uani 1 1 d . . . C9 C -0.1742(4) 0.1838(3) -0.0220(5) 0.0292(13) Uani 1 1 d . G . C10 C 0.1384(8) 0.0696(5) -0.1899(10) 0.074(3) Uani 1 1 d U . . H10 H 0.1659 0.0934 -0.2495 0.088 Uiso 1 1 calc R A 2 C11 C 0.0623(5) 0.3718(3) 0.1763(6) 0.0366(15) Uani 1 1 d . E . C12 C 0.0619(8) 0.4337(4) 0.1766(10) 0.072 Uani 1 1 d . . . H12A H 0.1048 0.4559 0.1268 0.086 Uiso 0.50 1 d PR B 1 C13 C 0.0000 0.4658(5) 0.2500 0.052 Uani 1 2 d S . . H13 H 0.0000 0.5084 0.2500 0.062 Uiso 1 2 calc SR . . C15 C 0.1933(8) -0.0155(5) -0.3059(9) 0.075 Uani 1 1 d . . . H15A H 0.2080 0.0167 -0.3617 0.112 Uiso 1 1 calc R C 2 H15B H 0.1559 -0.0460 -0.3470 0.112 Uiso 1 1 calc R C 2 H15C H 0.2505 -0.0339 -0.2757 0.112 Uiso 1 1 calc R C 2 C16 C 0.0970(9) -0.0300(6) -0.1190(12) 0.090 Uani 1 1 d . . . H16A H 0.1433 -0.0456 -0.0625 0.135 Uiso 1 1 calc R D 2 H16B H 0.0670 -0.0635 -0.1609 0.135 Uiso 1 1 calc R D 2 H16C H 0.0508 -0.0070 -0.0758 0.135 Uiso 1 1 calc R D 2 C17 C 0.0000 0.3411(5) 0.2500 0.035(2) Uani 1 2 d S . . H17 H 0.0000 0.2985 0.2500 0.042 Uiso 1 2 calc SR E . Cl1 Cl -0.39035(17) 0.13712(15) 0.2532(2) 0.0715(8) Uani 1 1 d . . . Cl2 Cl 0.1163(4) 0.4741(3) 0.0557(6) 0.0870(19) Uani 0.50 1 d P E 2 N1 N 0.1416(9) 0.0093(5) -0.2056(11) 0.106(4) Uani 1 1 d . F 2 O1 O -0.0206(4) 0.2048(3) -0.0781(5) 0.0467(14) Uani 1 1 d . G 2 O2 O 0.1032(5) 0.0971(3) -0.1053(6) 0.0605(15) Uani 1 1 d U F 2 O3 O 0.2860(3) 0.1520(2) -0.1085(5) 0.0426(12) Uani 1 1 d . . 2 O4 O 0.0927(4) 0.2929(2) 0.0393(5) 0.0420(13) Uani 1 1 d . H 2 O5 O -0.1198(4) 0.1634(3) 0.3616(4) 0.0445(13) Uani 1 1 d . . 2 O7 O -0.2483(3) 0.2175(2) 0.3847(4) 0.0371(11) Uani 1 1 d . . 2 O8 O -0.1302(4) 0.2030(3) -0.2226(4) 0.0458(14) Uani 1 1 d . . 2 Pr1 Pr 0.14037(2) 0.205121(16) -0.07025(3) 0.02493(17) Uani 1 1 d . . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(4) 0.069(5) 0.028(4) -0.001(3) 0.004(3) -0.012(4) C2 0.031(3) 0.049(4) 0.017(3) -0.001(3) 0.000(2) 0.000(3) C3 0.026(3) 0.045(4) 0.018(3) 0.000(3) -0.002(2) -0.004(3) C4 0.035(4) 0.059(4) 0.020(3) -0.005(3) -0.003(3) -0.006(3) C5 0.033(4) 0.079(6) 0.032(4) -0.002(4) -0.002(3) -0.013(4) C6 0.029(4) 0.043(4) 0.017(3) -0.003(2) 0.000(3) 0.000(3) C7 0.031(4) 0.050(4) 0.026(3) 0.002(3) 0.001(3) 0.006(3) C8 0.036(4) 0.044(4) 0.018(3) 0.000(3) 0.004(3) -0.004(3) C9 0.027(3) 0.042(4) 0.018(3) -0.004(3) -0.002(2) 0.003(3) C10 0.090(8) 0.057(6) 0.074(7) -0.019(5) 0.004(5) -0.002(5) C11 0.033(4) 0.044(4) 0.033(4) 0.001(3) 0.005(3) 0.002(3) C12 0.080 0.044 0.094 0.016 0.048 0.003 C13 0.053 0.043 0.059 0.000 0.017 0.000 C15 0.083 0.076 0.066 -0.048 0.014 0.013 C16 0.091 0.084 0.096 0.016 0.014 0.029 C17 0.036(5) 0.036(5) 0.034(5) 0.000 0.003(4) 0.000 Cl1 0.0493(12) 0.125(2) 0.0405(11) -0.0012(12) 0.0128(9) -0.0330(13) Cl2 0.092(4) 0.068(3) 0.103(4) 0.038(3) 0.055(3) 0.009(3) N1 0.136(10) 0.069(7) 0.112(9) -0.010(6) 0.002(8) 0.007(6) O1 0.030(3) 0.082(4) 0.027(3) -0.004(2) 0.000(2) -0.002(2) O2 0.060(4) 0.060(4) 0.061(4) -0.008(3) 0.003(3) -0.006(3) O3 0.032(3) 0.054(3) 0.042(3) -0.013(2) 0.003(2) 0.000(2) O4 0.032(3) 0.059(3) 0.035(3) -0.013(2) 0.003(2) -0.003(2) O5 0.041(3) 0.069(4) 0.024(2) -0.006(2) -0.007(2) 0.015(3) O7 0.035(3) 0.056(3) 0.020(2) -0.004(2) 0.001(2) 0.000(2) O8 0.035(3) 0.086(4) 0.016(2) 0.006(2) 0.000(2) -0.002(2) Pr1 0.0197(2) 0.0447(3) 0.0104(2) -0.00297(12) -0.00024(14) -0.00186(13) _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 C5 1.386(10) . ? C1 C2 1.387(10) . ? C1 Cl1 1.728(7) . ? C2 C3 1.371(9) . ? C2 C8 1.501(9) . ? C3 C9 1.386(8) . ? C3 H3 0.9300 . ? C4 C5 1.372(10) . ? C4 C9 1.395(9) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 O1 1.228(9) . ? C6 O8 1.258(9) . ? C6 C9 1.487(9) . ? C7 O3 1.233(9) 7 ? C7 O4 1.253(9) . ? C7 C11 1.511(9) . ? C8 O5 1.246(9) . ? C8 O7 1.273(8) . ? C8 Pr1 2.882(6) 2 ? C10 O2 1.224(11) . ? C10 N1 1.329(14) . ? C10 H10 0.9300 . ? C11 C12 1.351(12) . ? C11 C17 1.385(8) . ? C12 C13 1.396(11) . ? C12 Cl2 1.786(10) . ? C12 H12A 0.9600 . ? C13 C12 1.396(11) 2 ? C13 H13 0.9300 . ? C15 N1 1.444(14) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 N1 1.439(16) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C11 1.385(8) 2 ? C17 H17 0.9300 . ? Cl2 H12A 0.8962 . ? O1 Pr1 2.292(5) . ? O2 Pr1 2.445(6) . ? O3 C7 1.233(9) 7 ? O3 Pr1 2.421(5) . ? O4 Pr1 2.371(5) . ? O5 Pr1 2.493(5) 2 ? O7 Pr1 2.375(5) 8_456 ? O7 Pr1 2.546(5) 2 ? O8 Pr1 2.282(5) 2_554 ? Pr1 O8 2.282(5) 2_554 ? Pr1 O7 2.375(5) 8 ? Pr1 O5 2.493(5) 2 ? Pr1 O7 2.546(5) 2 ? Pr1 C8 2.882(6) 2 ? Pr1 Pr1 3.9736(7) 7 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C5 C1 C2 122.0(7) . . ? C5 C1 Cl1 118.0(6) . . ? C2 C1 Cl1 119.9(5) . . ? C3 C2 C1 118.1(6) . . ? C3 C2 C8 119.2(6) . . ? C1 C2 C8 122.6(6) . . ? C2 C3 C9 121.5(6) . . ? C2 C3 H3 119.2 . . ? C9 C3 H3 119.2 . . ? C5 C4 C9 120.8(6) . . ? C5 C4 H4 119.6 . . ? C9 C4 H4 119.6 . . ? C4 C5 C1 118.6(7) . . ? C4 C5 H5 120.7 . . ? C1 C5 H5 120.7 . . ? O1 C6 O8 125.1(7) . . ? O1 C6 C9 117.9(6) . . ? O8 C6 C9 116.9(6) . . ? O3 C7 O4 127.1(7) 7 . ? O3 C7 C11 118.0(6) 7 . ? O4 C7 C11 114.9(6) . . ? O5 C8 O7 121.5(6) . . ? O5 C8 C2 119.3(6) . . ? O7 C8 C2 119.2(6) . . ? O5 C8 Pr1 59.5(3) . 2 ? O7 C8 Pr1 62.0(3) . 2 ? C2 C8 Pr1 178.5(5) . 2 ? C3 C9 C4 118.9(6) . . ? C3 C9 C6 120.6(6) . . ? C4 C9 C6 120.5(6) . . ? O2 C10 N1 127.0(12) . . ? O2 C10 H10 116.5 . . ? N1 C10 H10 116.5 . . ? C12 C11 C17 118.7(7) . . ? C12 C11 C7 122.3(7) . . ? C17 C11 C7 119.0(7) . . ? C11 C12 C13 120.4(8) . . ? C11 C12 Cl2 119.4(7) . . ? C13 C12 Cl2 118.1(7) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 119.5 . . ? Cl2 C12 H12A 15.2 . . ? C12 C13 C12 119.7(11) . 2 ? C12 C13 H13 120.2 . . ? C12 C13 H13 120.2 2 . ? N1 C15 H15A 109.5 . . ? N1 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N1 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C11 C17 C11 122.2(9) 2 . ? C11 C17 H17 118.9 2 . ? C11 C17 H17 118.9 . . ? C12 Cl2 H12A 16.3 . . ? C10 N1 C16 119.2(11) . . ? C10 N1 C15 119.4(11) . . ? C16 N1 C15 121.4(10) . . ? C6 O1 Pr1 161.9(5) . . ? C10 O2 Pr1 120.2(7) . . ? C7 O3 Pr1 135.5(5) 7 . ? C7 O4 Pr1 138.3(5) . . ? C8 O5 Pr1 95.0(4) . 2 ? C8 O7 Pr1 156.9(5) . 8_456 ? C8 O7 Pr1 91.8(4) . 2 ? Pr1 O7 Pr1 107.66(18) 8_456 2 ? C6 O8 Pr1 164.5(5) . 2_554 ? O8 Pr1 O1 85.34(19) 2_554 . ? O8 Pr1 O4 120.7(2) 2_554 . ? O1 Pr1 O4 74.07(19) . . ? O8 Pr1 O7 80.52(18) 2_554 8 ? O1 Pr1 O7 131.69(19) . 8 ? O4 Pr1 O7 74.33(18) . 8 ? O8 Pr1 O3 81.62(19) 2_554 . ? O1 Pr1 O3 148.40(18) . . ? O4 Pr1 O3 136.95(18) . . ? O7 Pr1 O3 74.16(17) 8 . ? O8 Pr1 O2 79.3(2) 2_554 . ? O1 Pr1 O2 77.2(2) . . ? O4 Pr1 O2 142.8(2) . . ? O7 Pr1 O2 142.75(19) 8 . ? O3 Pr1 O2 72.2(2) . . ? O8 Pr1 O5 155.04(19) 2_554 2 ? O1 Pr1 O5 84.14(18) . 2 ? O4 Pr1 O5 77.69(19) . 2 ? O7 Pr1 O5 122.89(16) 8 2 ? O3 Pr1 O5 95.84(18) . 2 ? O2 Pr1 O5 76.4(2) . 2 ? O8 Pr1 O7 145.96(17) 2_554 2 ? O1 Pr1 O7 128.18(17) . 2 ? O4 Pr1 O7 71.37(18) . 2 ? O7 Pr1 O7 72.34(18) 8 2 ? O3 Pr1 O7 71.60(17) . 2 ? O2 Pr1 O7 110.77(19) . 2 ? O5 Pr1 O7 51.71(15) 2 2 ? O8 Pr1 C8 164.9(2) 2_554 2 ? O1 Pr1 C8 106.26(19) . 2 ? O4 Pr1 C8 72.6(2) . 2 ? O7 Pr1 C8 97.95(18) 8 2 ? O3 Pr1 C8 83.53(18) . 2 ? O2 Pr1 C8 93.7(2) . 2 ? O5 Pr1 C8 25.51(18) 2 2 ? O7 Pr1 C8 26.20(18) 2 2 ? O8 Pr1 Pr1 115.63(14) 2_554 7 ? O1 Pr1 Pr1 142.52(14) . 7 ? O4 Pr1 Pr1 68.52(13) . 7 ? O7 Pr1 Pr1 37.63(11) 8 7 ? O3 Pr1 Pr1 68.57(12) . 7 ? O2 Pr1 Pr1 134.66(16) . 7 ? O5 Pr1 Pr1 85.84(11) 2 7 ? O7 Pr1 Pr1 34.72(11) 2 7 ? C8 Pr1 Pr1 60.51(14) 2 7 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.331 _refine_diff_density_min -2.573 _refine_diff_density_rms 0.161