# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Robert LaDuca' _publ_contact_author_email LADUCA@MSU.EDU _publ_section_title ; Cadmium Dicarboxylate Coordination Polymers Incorporating a Long-Spanning Hydrogen-Bonding Capable Organodiimine: In Situ Alkene Isomerization and an Unprecedented Chiral 658 Two-Dimensional Network ; loop_ _publ_author_name 'Robert LaDuca' 'David P. Martin' 'Ronald M Supkowski' # Attachment '0cdfumarate4bpmp.cif' data_mono _database_code_depnum_ccdc_archive 'CCDC 685269' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 Cd N4 O8' _chemical_formula_weight 566.88 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(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.044(3) _cell_length_b 13.615(4) _cell_length_c 10.092(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.97(3) _cell_angle_gamma 90.00 _cell_volume 1220.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 13362 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 580 _exptl_absorpt_coefficient_mu 0.945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6787 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13362 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_sigmaI/netI 0.0395 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 28.14 _reflns_number_total 2810 _reflns_number_gt 2089 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0295P)^2^+0.2406P] 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 2810 _refine_ls_number_parameters 163 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0260 _refine_ls_wR_factor_ref 0.0628 _refine_ls_wR_factor_gt 0.0578 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.037 _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 Cd1 Cd 1.0000 0.0000 1.0000 0.01419(8) Uani 1 2 d S . . O1 O 0.98673(18) 0.04524(13) 1.21426(15) 0.0216(4) Uani 1 1 d . . . O1W O 0.2885(2) 0.29328(12) 0.06860(19) 0.0280(4) Uani 1 1 d D . . H1WB H 0.352(3) 0.3299(17) 0.038(3) 0.034 Uiso 1 1 d D . . H1WA H 0.242(3) 0.3316(17) 0.111(2) 0.034 Uiso 1 1 d D . . O2 O 0.8634(2) -0.08178(13) 1.28335(16) 0.0267(4) Uani 1 1 d . . . O3 O 1.19895(19) 0.10747(12) 0.98477(17) 0.0219(4) Uani 1 1 d D . . H3A H 1.191(3) 0.1092(17) 0.9018(16) 0.026 Uiso 1 1 d D . . H3B H 1.216(3) 0.1659(13) 1.015(2) 0.026 Uiso 1 1 d D . . N1 N 0.8174(2) 0.11669(14) 0.91732(19) 0.0189(4) Uani 1 1 d . . . N2 N 0.4830(2) 0.40751(13) 0.92645(19) 0.0158(4) Uani 1 1 d . . . C1 C 0.8449(3) 0.19060(17) 0.8382(2) 0.0227(5) Uani 1 1 d . . . H1 H 0.9366 0.1916 0.8092 0.027 Uiso 1 1 calc R . . C2 C 0.7435(3) 0.26548(17) 0.7974(2) 0.0222(5) Uani 1 1 d . . . H2 H 0.7671 0.3152 0.7418 0.027 Uiso 1 1 calc R . . C3 C 0.6064(3) 0.26633(16) 0.8397(2) 0.0195(5) Uani 1 1 d . . . C4 C 0.5763(3) 0.18757(17) 0.9189(2) 0.0212(5) Uani 1 1 d . . . H4 H 0.4844 0.1836 0.9471 0.025 Uiso 1 1 calc R . . C5 C 0.6834(3) 0.11597(17) 0.9550(2) 0.0222(5) Uani 1 1 d . . . H5 H 0.6616 0.0643 1.0084 0.027 Uiso 1 1 calc R . . C6 C 0.4970(3) 0.35053(17) 0.8052(2) 0.0233(5) Uani 1 1 d . . . H6A H 0.5314 0.3934 0.7405 0.028 Uiso 1 1 calc R . . H6B H 0.3990 0.3250 0.7637 0.028 Uiso 1 1 calc R . . C7 C 0.6311(2) 0.44526(16) 0.9954(2) 0.0173(5) Uani 1 1 d . . . H7A H 0.6753 0.4845 0.9328 0.021 Uiso 1 1 calc R . . H7B H 0.6981 0.3905 1.0246 0.021 Uiso 1 1 calc R . . C8 C 0.3850(3) 0.49284(16) 0.8838(2) 0.0191(5) Uani 1 1 d . . . H8A H 0.2865 0.4703 0.8386 0.023 Uiso 1 1 calc R . . H8B H 0.4277 0.5322 0.8204 0.023 Uiso 1 1 calc R . . C9 C 0.9446(2) -0.00643(18) 1.3043(2) 0.0182(5) Uani 1 1 d . . . C10 C 1.0001(3) 0.02766(17) 1.4465(2) 0.0186(5) Uani 1 1 d . . . H10 H 1.0367 0.0915 1.4599 0.022 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.01579(12) 0.01593(12) 0.01127(11) 0.00090(11) 0.00363(8) 0.00202(11) O1 0.0281(9) 0.0247(9) 0.0129(8) 0.0005(7) 0.0065(7) -0.0008(8) O1W 0.0356(11) 0.0169(9) 0.0356(11) -0.0020(8) 0.0168(9) 0.0000(8) O2 0.0332(10) 0.0314(10) 0.0164(9) -0.0038(7) 0.0068(7) -0.0121(8) O3 0.0272(10) 0.0213(9) 0.0168(9) -0.0023(7) 0.0035(7) -0.0060(8) N1 0.0216(10) 0.0178(10) 0.0178(10) 0.0001(8) 0.0051(8) 0.0028(8) N2 0.0153(10) 0.0136(9) 0.0176(11) -0.0018(8) 0.0010(8) 0.0034(8) C1 0.0214(13) 0.0244(13) 0.0244(13) 0.0010(10) 0.0097(10) 0.0037(10) C2 0.0283(13) 0.0195(12) 0.0196(12) 0.0036(10) 0.0068(10) 0.0027(10) C3 0.0235(13) 0.0166(11) 0.0165(12) -0.0050(9) -0.0005(10) 0.0028(10) C4 0.0184(12) 0.0190(12) 0.0278(13) -0.0026(10) 0.0088(10) 0.0009(10) C5 0.0268(14) 0.0198(12) 0.0219(13) -0.0009(10) 0.0096(11) 0.0001(10) C6 0.0273(14) 0.0201(12) 0.0200(13) -0.0038(10) -0.0017(10) 0.0077(10) C7 0.0117(11) 0.0174(12) 0.0222(12) 0.0003(10) 0.0017(9) 0.0030(9) C8 0.0159(10) 0.0172(11) 0.0223(11) -0.0004(10) -0.0006(8) 0.0029(10) C9 0.0142(10) 0.0269(12) 0.0140(10) 0.0000(11) 0.0037(8) 0.0071(12) C10 0.0159(11) 0.0234(13) 0.0174(11) -0.0050(9) 0.0053(9) 0.0013(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 Cd1 O1 2.2733(18) . ? Cd1 O1 2.2733(18) 3_757 ? Cd1 N1 2.3286(19) . ? Cd1 N1 2.3287(19) 3_757 ? Cd1 O3 2.3468(17) 3_757 ? Cd1 O3 2.3468(17) . ? O1 C9 1.264(3) . ? O1W H1WB 0.859(16) . ? O1W H1WA 0.836(16) . ? O2 C9 1.256(3) . ? O3 H3A 0.827(16) . ? O3 H3B 0.856(16) . ? N1 C1 1.337(3) . ? N1 C5 1.338(3) . ? N2 C6 1.474(3) . ? N2 C8 1.475(3) . ? N2 C7 1.479(3) . ? C1 C2 1.381(3) . ? C1 H1 0.9300 . ? C2 C3 1.386(3) . ? C2 H2 0.9300 . ? C3 C4 1.395(3) . ? C3 C6 1.511(3) . ? C4 C5 1.374(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.512(3) 3_667 ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C7 1.512(3) 3_667 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.502(3) . ? C10 C10 1.316(5) 3_758 ? C10 H10 0.9300 . ? 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 Cd1 O1 180.00(9) . 3_757 ? O1 Cd1 N1 89.64(7) . . ? O1 Cd1 N1 90.36(7) 3_757 . ? O1 Cd1 N1 90.36(7) . 3_757 ? O1 Cd1 N1 89.64(7) 3_757 3_757 ? N1 Cd1 N1 180.0 . 3_757 ? O1 Cd1 O3 85.80(6) . 3_757 ? O1 Cd1 O3 94.20(6) 3_757 3_757 ? N1 Cd1 O3 87.05(7) . 3_757 ? N1 Cd1 O3 92.95(7) 3_757 3_757 ? O1 Cd1 O3 94.20(6) . . ? O1 Cd1 O3 85.80(6) 3_757 . ? N1 Cd1 O3 92.95(7) . . ? N1 Cd1 O3 87.05(7) 3_757 . ? O3 Cd1 O3 180.0 3_757 . ? C9 O1 Cd1 127.62(15) . . ? H1WB O1W H1WA 105(2) . . ? Cd1 O3 H3A 99.4(18) . . ? Cd1 O3 H3B 130.0(18) . . ? H3A O3 H3B 108(2) . . ? C1 N1 C5 117.2(2) . . ? C1 N1 Cd1 121.85(16) . . ? C5 N1 Cd1 120.82(16) . . ? C6 N2 C8 108.31(17) . . ? C6 N2 C7 111.10(18) . . ? C8 N2 C7 107.69(17) . . ? N1 C1 C2 123.0(2) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C1 C2 C3 119.8(2) . . ? C1 C2 H2 120.1 . . ? C3 C2 H2 120.1 . . ? C2 C3 C4 117.0(2) . . ? C2 C3 C6 121.3(2) . . ? C4 C3 C6 121.6(2) . . ? C5 C4 C3 119.5(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? N1 C5 C4 123.4(2) . . ? N1 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? N2 C6 C3 111.35(19) . . ? N2 C6 H6A 109.4 . . ? C3 C6 H6A 109.4 . . ? N2 C6 H6B 109.4 . . ? C3 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N2 C7 C8 110.84(18) . 3_667 ? N2 C7 H7A 109.5 . . ? C8 C7 H7A 109.5 3_667 . ? N2 C7 H7B 109.5 . . ? C8 C7 H7B 109.5 3_667 . ? H7A C7 H7B 108.1 . . ? N2 C8 C7 110.38(18) . 3_667 ? N2 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 3_667 . ? N2 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 3_667 . ? H8A C8 H8B 108.1 . . ? O2 C9 O1 125.5(2) . . ? O2 C9 C10 119.4(2) . . ? O1 C9 C10 115.1(2) . . ? C10 C10 C9 123.7(3) 3_758 . ? C10 C10 H10 118.2 3_758 . ? C9 C10 H10 118.2 . . ? 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 H1WB N2 0.859(16) 2.075(17) 2.921(3) 168(3) 1_554 O1W H1WA O2 0.836(16) 1.957(17) 2.792(2) 177(3) 2_656 O3 H3A O2 0.827(16) 1.877(17) 2.680(3) 163(2) 3_757 O3 H3B O1W 0.856(16) 1.896(17) 2.740(2) 169(3) 1_656 _diffrn_measured_fraction_theta_max 0.941 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.402 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.077 # Attachment '0cdsuc4bpmpfinal.cif' data_ortho _database_code_depnum_ccdc_archive 'CCDC 685270' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H32 Cd N4 O7' _chemical_formula_weight 564.91 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.24920(10) _cell_length_b 12.9812(2) _cell_length_c 16.7710(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2449.04(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 11264 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 29.14 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.532 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.939 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.813 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11264 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 29.14 _reflns_number_total 5834 _reflns_number_gt 5485 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0252P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.024(15) _refine_ls_number_reflns 5834 _refine_ls_number_parameters 314 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0243 _refine_ls_wR_factor_ref 0.0537 _refine_ls_wR_factor_gt 0.0526 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 Cd1 Cd -0.007633(12) 0.232644(11) 0.117776(9) 0.01782(4) Uani 1 1 d . . . O1 O 0.09169(13) 0.34168(12) 0.01920(9) 0.0226(4) Uani 1 1 d . . . O1W O 0.21039(16) 0.25593(15) 0.34304(12) 0.0378(4) Uani 1 1 d D . . H1WA H 0.224(2) 0.3137(14) 0.3261(16) 0.045 Uiso 1 1 d D . . H1WB H 0.2712(18) 0.2218(19) 0.3377(16) 0.045 Uiso 1 1 d D . . O2 O 0.12447(15) 0.37007(13) 0.14694(11) 0.0260(4) Uani 1 1 d . . . O2W O 0.25733(18) 0.44340(15) 0.27268(11) 0.0360(5) Uani 1 1 d D . . H2WA H 0.219(2) 0.4959(17) 0.2897(16) 0.043 Uiso 1 1 d D . . H2WB H 0.220(2) 0.430(2) 0.2289(11) 0.043 Uiso 1 1 d D . . O3 O 0.38597(14) 0.35145(12) -0.01227(10) 0.0242(4) Uani 1 1 d . . . O4 O 0.35600(14) 0.40685(13) -0.13486(10) 0.0243(4) Uani 1 1 d . . . O5 O 0.01315(16) 0.21385(16) 0.25725(10) 0.0415(5) Uani 1 1 d . . . H5A H 0.070(2) 0.234(2) 0.2838(17) 0.050 Uiso 1 1 d . . . N1 N 0.14687(16) 0.11346(15) 0.10249(12) 0.0225(5) Uani 1 1 d . . . N2 N 0.42195(16) -0.19610(15) 0.07246(11) 0.0217(4) Uani 1 1 d . . . N3 N 0.55316(17) -0.34775(15) 0.16207(11) 0.0219(4) Uani 1 1 d . . . N4 N 0.83332(17) -0.65418(15) 0.14115(11) 0.0209(4) Uani 1 1 d . . . C1 C 0.1259(2) 0.01163(17) 0.10087(14) 0.0237(5) Uani 1 1 d . . . H1 H 0.0493 -0.0121 0.1160 0.028 Uiso 1 1 calc R . . C2 C 0.2093(2) -0.05990(18) 0.07855(13) 0.0243(5) Uani 1 1 d . . . H2 H 0.1902 -0.1312 0.0784 0.029 Uiso 1 1 calc R . . C3 C 0.3221(2) -0.02682(18) 0.05618(13) 0.0223(5) Uani 1 1 d . . . C4 C 0.3453(2) 0.07689(18) 0.06064(14) 0.0246(5) Uani 1 1 d . . . H4 H 0.4224 0.1022 0.0482 0.030 Uiso 1 1 calc R . . C5 C 0.25669(19) 0.14451(18) 0.08321(14) 0.0248(5) Uani 1 1 d . . . H5 H 0.2744 0.2160 0.0851 0.030 Uiso 1 1 calc R . . C6 C 0.4137(2) -0.10203(19) 0.02494(15) 0.0284(6) Uani 1 1 d . . . H6A H 0.3931 -0.1206 -0.0306 0.034 Uiso 1 1 calc R . . H6B H 0.4924 -0.0679 0.0241 0.034 Uiso 1 1 calc R . . C7 C 0.4673(2) -0.17437(17) 0.15263(14) 0.0286(6) Uani 1 1 d . . . H7A H 0.4141 -0.1248 0.1798 0.034 Uiso 1 1 calc R . . H7B H 0.5473 -0.1429 0.1488 0.034 Uiso 1 1 calc R . . C8 C 0.4744(2) -0.27293(19) 0.20077(13) 0.0301(5) Uani 1 1 d . . . H8A H 0.5047 -0.2573 0.2549 0.036 Uiso 1 1 calc R . . H8B H 0.3939 -0.3029 0.2063 0.036 Uiso 1 1 calc R . . C9 C 0.5091(2) -0.36795(15) 0.08174(12) 0.0237(5) Uani 1 1 d . . . H9A H 0.4294 -0.4000 0.0850 0.028 Uiso 1 1 calc R . . H9B H 0.5629 -0.4170 0.0546 0.028 Uiso 1 1 calc R . . C10 C 0.5014(2) -0.26928(16) 0.03331(13) 0.0254(4) Uani 1 1 d . . . H10A H 0.5815 -0.2386 0.0279 0.030 Uiso 1 1 calc R . . H10B H 0.4712 -0.2850 -0.0208 0.030 Uiso 1 1 calc R . . C11 C 0.5533(2) -0.44478(18) 0.20835(14) 0.0263(5) Uani 1 1 d . . . H11A H 0.4752 -0.4792 0.2022 0.032 Uiso 1 1 calc R . . H11B H 0.5643 -0.4287 0.2656 0.032 Uiso 1 1 calc R . . C12 C 0.8546(2) -0.56960(18) 0.18471(14) 0.0257(5) Uani 1 1 d . . . H12 H 0.9337 -0.5568 0.2020 0.031 Uiso 1 1 calc R . . C13 C 0.7671(2) -0.50020(19) 0.20562(15) 0.0273(6) Uani 1 1 d . . . H13 H 0.7864 -0.4410 0.2362 0.033 Uiso 1 1 calc R . . C14 C 0.6502(2) -0.51738(18) 0.18164(13) 0.0227(5) Uani 1 1 d . . . C15 C 0.6286(2) -0.60370(17) 0.13540(14) 0.0238(5) Uani 1 1 d . . . H15 H 0.5506 -0.6176 0.1164 0.029 Uiso 1 1 calc R . . C16 C 0.72137(19) -0.66977(16) 0.11697(14) 0.0230(5) Uani 1 1 d . . . H16 H 0.7047 -0.7290 0.0857 0.028 Uiso 1 1 calc R . . C17 C 0.14015(19) 0.39207(17) 0.07436(15) 0.0196(5) Uani 1 1 d . . . C18 C 0.2190(2) 0.48312(17) 0.05599(14) 0.0236(5) Uani 1 1 d . . . H18A H 0.2925 0.4771 0.0881 0.028 Uiso 1 1 calc R . . H18B H 0.1776 0.5467 0.0731 0.028 Uiso 1 1 calc R . . C19 C 0.2536(2) 0.49445(18) -0.03118(14) 0.0233(5) Uani 1 1 d . . . H19A H 0.1805 0.4936 -0.0640 0.028 Uiso 1 1 calc R . . H19B H 0.2923 0.5622 -0.0387 0.028 Uiso 1 1 calc R . . C20 C 0.3367(2) 0.41095(17) -0.06088(15) 0.0207(5) Uani 1 1 d . . . C21 C -0.0732(2) 0.1774(3) 0.30957(16) 0.0440(8) Uani 1 1 d . . . H21A H -0.1521 0.1872 0.2860 0.066 Uiso 1 1 calc R . . H21B H -0.0683 0.2155 0.3599 0.066 Uiso 1 1 calc R . . H21C H -0.0599 0.1040 0.3196 0.066 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cd1 0.01501(7) 0.01805(7) 0.02040(8) -0.00020(6) -0.00032(7) -0.00058(7) O1 0.0203(8) 0.0233(8) 0.0243(9) -0.0022(7) -0.0030(7) -0.0014(7) O1W 0.0289(9) 0.0363(11) 0.0481(12) 0.0016(9) -0.0101(9) -0.0017(8) O2 0.0274(9) 0.0273(9) 0.0231(9) 0.0000(7) 0.0031(7) -0.0069(7) O2W 0.0389(12) 0.0350(11) 0.0341(11) -0.0090(9) -0.0104(9) 0.0079(9) O3 0.0218(8) 0.0241(8) 0.0267(9) 0.0014(7) 0.0019(7) 0.0050(7) O4 0.0246(9) 0.0265(8) 0.0219(10) -0.0009(7) 0.0049(7) 0.0048(7) O5 0.0308(10) 0.0717(14) 0.0219(9) 0.0106(8) -0.0059(8) -0.0219(12) N1 0.0186(10) 0.0254(10) 0.0235(13) 0.0025(9) -0.0018(9) 0.0034(8) N2 0.0204(10) 0.0234(9) 0.0214(10) -0.0005(8) -0.0008(8) 0.0046(8) N3 0.0250(10) 0.0204(9) 0.0204(10) -0.0025(8) -0.0012(8) 0.0057(8) N4 0.0217(10) 0.0195(9) 0.0214(11) 0.0000(8) 0.0001(8) 0.0007(8) C1 0.0182(11) 0.0240(11) 0.0289(14) 0.0024(10) -0.0023(10) 0.0000(9) C2 0.0222(12) 0.0201(11) 0.0306(14) 0.0009(10) -0.0051(11) 0.0001(10) C3 0.0210(12) 0.0286(12) 0.0173(12) 0.0037(9) -0.0009(10) 0.0051(10) C4 0.0171(12) 0.0294(13) 0.0273(13) 0.0093(10) 0.0030(10) 0.0031(10) C5 0.0209(12) 0.0210(11) 0.0326(14) 0.0045(10) -0.0012(10) -0.0010(9) C6 0.0264(13) 0.0290(13) 0.0297(14) 0.0047(11) 0.0035(11) 0.0108(11) C7 0.0322(14) 0.0255(12) 0.0281(13) -0.0063(10) -0.0043(11) 0.0126(10) C8 0.0377(14) 0.0325(12) 0.0200(11) -0.0027(10) 0.0017(10) 0.0176(13) C9 0.0269(13) 0.0209(9) 0.0234(11) -0.0034(8) -0.0013(12) 0.0003(12) C10 0.0279(12) 0.0249(10) 0.0232(11) -0.0014(8) 0.0012(11) 0.0083(17) C11 0.0293(13) 0.0254(12) 0.0243(13) 0.0029(10) 0.0066(11) 0.0089(10) C12 0.0239(13) 0.0246(12) 0.0286(14) -0.0018(10) -0.0029(11) 0.0024(10) C13 0.0353(15) 0.0204(12) 0.0261(14) -0.0029(10) -0.0055(12) 0.0036(11) C14 0.0238(13) 0.0238(11) 0.0207(12) 0.0062(9) 0.0040(10) 0.0060(10) C15 0.0194(11) 0.0261(11) 0.0259(14) 0.0006(9) -0.0017(10) 0.0005(9) C16 0.0256(12) 0.0197(10) 0.0237(12) -0.0019(10) 0.0007(11) 0.0007(8) C17 0.0141(11) 0.0208(11) 0.0239(13) -0.0004(9) 0.0008(10) 0.0052(9) C18 0.0257(13) 0.0177(11) 0.0275(13) -0.0033(9) 0.0046(11) -0.0019(10) C19 0.0238(13) 0.0191(11) 0.0271(13) 0.0010(10) 0.0058(10) 0.0031(10) C20 0.0143(11) 0.0175(11) 0.0301(14) -0.0014(10) 0.0028(10) -0.0031(9) C21 0.0390(16) 0.066(2) 0.0275(15) -0.0005(14) 0.0067(13) -0.0167(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cd1 N1 2.3410(19) . ? Cd1 N4 2.3480(19) 1_465 ? Cd1 O5 2.3634(17) . ? Cd1 O2 2.3728(16) . ? Cd1 O4 2.3904(16) 4_455 ? Cd1 O3 2.3990(16) 4_455 ? Cd1 O1 2.4465(16) . ? O1 C17 1.257(3) . ? O2 C17 1.263(3) . ? O3 C20 1.252(3) . ? O3 Cd1 2.3990(16) 4 ? O4 C20 1.261(3) . ? O4 Cd1 2.3905(16) 4 ? O5 C21 1.391(3) . ? N1 C5 1.339(3) . ? N1 C1 1.343(3) . ? N2 C10 1.460(3) . ? N2 C6 1.461(3) . ? N2 C7 1.466(3) . ? N3 C9 1.459(3) . ? N3 C8 1.466(3) . ? N3 C11 1.480(3) . ? N4 C16 1.338(3) . ? N4 C12 1.340(3) . ? N4 Cd1 2.3481(19) 1_645 ? C1 C2 1.372(3) . ? C2 C3 1.392(3) . ? C3 C4 1.373(3) . ? C3 C6 1.512(3) . ? C4 C5 1.381(3) . ? C7 C8 1.515(3) . ? C9 C10 1.519(3) . ? C11 C14 1.510(3) . ? C12 C13 1.380(3) . ? C13 C14 1.392(3) . ? C14 C15 1.384(3) . ? C15 C16 1.386(3) . ? C17 C18 1.510(3) . ? C18 C19 1.520(3) . ? C19 C20 1.516(3) . ? C20 Cd1 2.730(2) 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 N1 Cd1 N4 175.98(7) . 1_465 ? N1 Cd1 O5 88.09(7) . . ? N4 Cd1 O5 88.55(7) 1_465 . ? N1 Cd1 O2 93.12(6) . . ? N4 Cd1 O2 88.42(7) 1_465 . ? O5 Cd1 O2 79.14(6) . . ? N1 Cd1 O4 89.36(6) . 4_455 ? N4 Cd1 O4 87.99(6) 1_465 4_455 ? O5 Cd1 O4 82.34(6) . 4_455 ? O2 Cd1 O4 161.21(6) . 4_455 ? N1 Cd1 O3 89.37(6) . 4_455 ? N4 Cd1 O3 91.59(6) 1_465 4_455 ? O5 Cd1 O3 137.09(6) . 4_455 ? O2 Cd1 O3 143.77(6) . 4_455 ? O4 Cd1 O3 54.80(5) 4_455 4_455 ? N1 Cd1 O1 88.24(6) . . ? N4 Cd1 O1 95.67(6) 1_465 . ? O5 Cd1 O1 133.11(6) . . ? O2 Cd1 O1 54.43(6) . . ? O4 Cd1 O1 144.32(5) 4_455 . ? O3 Cd1 O1 89.58(6) 4_455 . ? N1 Cd1 C20 89.23(7) . 4_455 ? N4 Cd1 C20 89.82(7) 1_465 4_455 ? O5 Cd1 C20 109.81(7) . 4_455 ? O2 Cd1 C20 170.83(7) . 4_455 ? O4 Cd1 C20 27.50(6) 4_455 4_455 ? O3 Cd1 C20 27.30(6) 4_455 4_455 ? O1 Cd1 C20 116.86(6) . 4_455 ? N1 Cd1 C17 91.12(6) . . ? N4 Cd1 C17 91.95(6) 1_465 . ? O5 Cd1 C17 106.24(7) . . ? O2 Cd1 C17 27.25(6) . . ? O4 Cd1 C17 171.42(6) 4_455 . ? O3 Cd1 C17 116.64(6) 4_455 . ? O1 Cd1 C17 27.18(6) . . ? C20 Cd1 C17 143.94(8) 4_455 . ? C17 O1 Cd1 90.10(14) . . ? C17 O2 Cd1 93.37(14) . . ? C20 O3 Cd1 91.21(14) . 4 ? C20 O4 Cd1 91.40(14) . 4 ? C21 O5 Cd1 126.17(16) . . ? C5 N1 C1 116.9(2) . . ? C5 N1 Cd1 120.83(15) . . ? C1 N1 Cd1 121.50(15) . . ? C10 N2 C6 109.72(18) . . ? C10 N2 C7 108.95(17) . . ? C6 N2 C7 111.21(18) . . ? C9 N3 C8 108.82(18) . . ? C9 N3 C11 109.36(17) . . ? C8 N3 C11 109.41(18) . . ? C16 N4 C12 117.2(2) . . ? C16 N4 Cd1 124.88(15) . 1_645 ? C12 N4 Cd1 117.85(16) . 1_645 ? N1 C1 C2 123.5(2) . . ? C1 C2 C3 119.2(2) . . ? C4 C3 C2 117.5(2) . . ? C4 C3 C6 121.5(2) . . ? C2 C3 C6 121.0(2) . . ? C3 C4 C5 120.0(2) . . ? N1 C5 C4 122.7(2) . . ? N2 C6 C3 113.20(19) . . ? N2 C7 C8 110.16(19) . . ? N3 C8 C7 110.82(19) . . ? N3 C9 C10 111.19(17) . . ? N2 C10 C9 110.07(19) . . ? N3 C11 C14 112.11(19) . . ? N4 C12 C13 123.1(2) . . ? C12 C13 C14 119.7(2) . . ? C15 C14 C13 117.2(2) . . ? C15 C14 C11 123.0(2) . . ? C13 C14 C11 119.8(2) . . ? C14 C15 C16 119.5(2) . . ? N4 C16 C15 123.2(2) . . ? O1 C17 O2 122.1(2) . . ? O1 C17 C18 120.8(2) . . ? O2 C17 C18 117.1(2) . . ? O1 C17 Cd1 62.72(12) . . ? O2 C17 Cd1 59.38(12) . . ? C18 C17 Cd1 175.99(17) . . ? C17 C18 C19 115.0(2) . . ? C20 C19 C18 113.9(2) . . ? O3 C20 O4 122.6(2) . . ? O3 C20 C19 120.0(2) . . ? O4 C20 C19 117.4(2) . . ? O3 C20 Cd1 61.49(12) . 4 ? O4 C20 Cd1 61.10(12) . 4 ? C19 C20 Cd1 177.39(16) . 4 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1WA O2W 0.817(17) 1.944(17) 2.756(3) 173(3) . O1W H1WB N3 0.820(16) 2.172(16) 2.982(3) 169(3) 3_655 O2W H2WA O4 0.855(16) 1.977(18) 2.794(2) 160(3) 2_565 O2W H2WB O2 0.861(16) 1.913(17) 2.754(3) 165(3) . O5 H5A O1W 0.82(3) 1.89(3) 2.700(2) 170(3) . _diffrn_measured_fraction_theta_max 0.944 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.429 _refine_diff_density_min -0.494 _refine_diff_density_rms 0.063