Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Williams, Ian' 'Chui, Stephen S-Y.' 'Lin, Candy Z-J.' 'Lipkowski, Janusz' 'Lo, Samuel M.-F.' 'Shek, Fanny L-Y.' 'Suwinska, Kinga' 'Wu, Mingmei' _publ_contact_author_name 'Dr Ian Duncan Williams' _publ_contact_author_address ; Department of Chemistry Hong Kong University of Science & Technology HONG KONG ; _publ_contact_author_email ianduncanw@yahoo.com.hk _journal_name_full 'Chemical Communications' _publ_section_title ; Physical Stability versus Chemical Lability in Microporous Metal Coordination Polymers: A comparison of [Cu(OH)(INA)]n and [Cu(INA)2]n INA = 1,4-(NC5H4CO2) ; data_candy2 _database_code_CSD 179661 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common '[Cu(PCA)(OH)]H2O' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C6 H7 Cu N O4' _chemical_formula_weight 220.67 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 3.53400(10) _cell_length_b 15.7680(5) _cell_length_c 13.0052(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.8850(13) _cell_angle_gamma 90.00 _cell_volume 719.48(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2071 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _diffrn_measurement_method 'CCD' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _exptl_crystal_description Bar _exptl_crystal_colour Turquoise _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.037 _exptl_crystal_density_method ? _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 3.004 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.97 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 3585 _diffrn_reflns_theta_max 30.00 _diffrn_reflns_av_R_equivalents 0.026 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2078 _reflns_number_observed 1813 _reflns_observed_criterion >2sigma(I) _diffrn_measurement_device 'KappaCCD' loop_ _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_wavelength_id all _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.06347 _diffrn_orient_matrix_UB_12 0.25521 _diffrn_orient_matrix_UB_13 -0.10988 _diffrn_orient_matrix_UB_21 0.00082 _diffrn_orient_matrix_UB_22 0.02490 _diffrn_orient_matrix_UB_23 0.05832 _diffrn_orient_matrix_UB_31 0.07702 _diffrn_orient_matrix_UB_32 -0.00782 _diffrn_orient_matrix_UB_33 0.00226 _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 40 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0178P)^2^+2.2086P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2038 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0512 _refine_ls_R_factor_obs 0.0364 _refine_ls_wR_factor_all 0.1216 _refine_ls_wR_factor_obs 0.0821 _refine_ls_goodness_of_fit_all 1.124 _refine_ls_goodness_of_fit_obs 1.136 _refine_ls_restrained_S_all 1.573 _refine_ls_restrained_S_obs 1.136 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.26242(9) 0.07802(2) 0.49492(2) 0.00888(10) Uani 1 d . . O1 O 0.3131(5) -0.02838(12) 0.57051(14) 0.0085(3) Uani 1 d . . H1 H 0.3502(5) -0.02395(12) 0.63608(14) 0.010 Uiso 1 d R . N1 N 0.2571(6) 0.17961(14) 0.4035(2) 0.0101(4) Uani 1 d . . C2 C 0.2548(7) 0.1654(2) 0.3011(2) 0.0127(5) Uani 1 d . . H2 H 0.1928(7) 0.1115(2) 0.2753(2) 0.015 Uiso 1 calc R . C3 C 0.3414(7) 0.2281(2) 0.2332(2) 0.0124(5) Uani 1 d . . H3 H 0.3370(7) 0.2164(2) 0.1630(2) 0.015 Uiso 1 calc R . C4 C 0.4350(7) 0.3086(2) 0.2712(2) 0.0115(5) Uani 1 d . . C5 C 0.4260(8) 0.3238(2) 0.3763(2) 0.0136(5) Uani 1 d . . H5 H 0.4800(8) 0.3776(2) 0.4037(2) 0.016 Uiso 1 calc R . C6 C 0.3355(7) 0.2580(2) 0.4397(2) 0.0127(5) Uani 1 d . . H6 H 0.3290(7) 0.2686(2) 0.5098(2) 0.015 Uiso 1 calc R . C10 C 0.5602(7) 0.3774(2) 0.2010(2) 0.0114(5) Uani 1 d . . O11 O 0.5370(6) 0.35786(13) 0.10595(14) 0.0134(4) Uani 1 d . . O12 O 0.6811(7) 0.44504(14) 0.2416(2) 0.0207(4) Uani 1 d . . O1W O 0.9245(19) 0.5464(2) 0.4130(3) 0.107(2) Uani 1 d . . H1W H 0.9069(19) 0.5130(2) 0.4635(3) 0.129 Uiso 0.50 d PR . H2W H 1.1505(19) 0.5656(2) 0.4169(3) 0.129 Uiso 0.50 d PR . H3W H 0.7691(19) 0.5876(2) 0.4127(3) 0.129 Uiso 0.50 d PR . H4W H 0.8797(19) 0.5191(2) 0.3565(3) 0.129 Uiso 0.50 d PR . 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 Cu1 0.0122(2) 0.0071(2) 0.0082(2) 0.00147(11) 0.00463(11) 0.00116(11) O1 0.0122(8) 0.0072(8) 0.0067(7) 0.0007(6) 0.0030(6) 0.0017(6) N1 0.0114(9) 0.0083(10) 0.0111(10) 0.0035(8) 0.0037(7) 0.0011(8) C2 0.0163(12) 0.0113(12) 0.0104(11) 0.0004(9) 0.0020(9) -0.0002(9) C3 0.0165(12) 0.0125(12) 0.0086(10) 0.0015(9) 0.0027(9) -0.0005(9) C4 0.0113(11) 0.0142(13) 0.0094(11) 0.0031(9) 0.0027(8) 0.0007(9) C5 0.0179(12) 0.0117(12) 0.0121(11) 0.0005(9) 0.0052(9) -0.0014(10) C6 0.0181(12) 0.0109(12) 0.0097(11) 0.0012(9) 0.0040(9) -0.0007(10) C10 0.0119(11) 0.0108(12) 0.0120(11) 0.0029(9) 0.0032(9) 0.0002(9) O11 0.0211(9) 0.0114(9) 0.0086(8) 0.0011(7) 0.0056(7) -0.0030(7) O12 0.0348(12) 0.0154(11) 0.0124(9) 0.0005(8) 0.0050(8) -0.0097(9) O1W 0.256(7) 0.036(2) 0.023(2) -0.0052(15) -0.014(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 Cu1 O1 1.942(2) . ? Cu1 O1 1.973(2) 3_656 ? Cu1 N1 1.994(2) . ? Cu1 O11 2.004(2) 4_566 ? Cu1 O1 2.249(2) 3_556 ? Cu1 Cu1 2.9727(6) 3_656 ? O1 Cu1 1.973(2) 3_656 ? O1 Cu1 2.249(2) 3_556 ? N1 C6 1.340(3) . ? N1 C2 1.349(3) . ? C2 C3 1.384(4) . ? C3 C4 1.388(4) . ? C4 C5 1.391(4) . ? C4 C10 1.517(4) . ? C5 C6 1.387(4) . ? C10 O12 1.243(3) . ? C10 O11 1.267(3) . ? O11 Cu1 2.004(2) 4_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 81.19(8) . 3_656 ? O1 Cu1 N1 171.80(8) . . ? O1 Cu1 N1 90.85(8) 3_656 . ? O1 Cu1 O11 95.26(8) . 4_566 ? O1 Cu1 O11 154.05(8) 3_656 4_566 ? N1 Cu1 O11 92.76(9) . 4_566 ? O1 Cu1 O1 85.14(7) . 3_556 ? O1 Cu1 O1 113.49(8) 3_656 3_556 ? N1 Cu1 O1 96.35(8) . 3_556 ? O11 Cu1 O1 91.63(7) 4_566 3_556 ? O1 Cu1 Cu1 40.99(5) . 3_656 ? O1 Cu1 Cu1 40.21(5) 3_656 3_656 ? N1 Cu1 Cu1 131.03(6) . 3_656 ? O11 Cu1 Cu1 131.05(6) 4_566 3_656 ? O1 Cu1 Cu1 102.08(5) 3_556 3_656 ? Cu1 O1 Cu1 98.81(8) . 3_656 ? Cu1 O1 Cu1 94.86(7) . 3_556 ? Cu1 O1 Cu1 113.49(8) 3_656 3_556 ? C6 N1 C2 118.5(2) . . ? C6 N1 Cu1 123.0(2) . . ? C2 N1 Cu1 117.0(2) . . ? N1 C2 C3 122.4(3) . . ? C2 C3 C4 119.2(2) . . ? C3 C4 C5 118.3(2) . . ? C3 C4 C10 120.9(2) . . ? C5 C4 C10 120.7(2) . . ? C6 C5 C4 119.3(3) . . ? N1 C6 C5 122.3(2) . . ? O12 C10 O11 127.0(2) . . ? O12 C10 C4 117.9(2) . . ? O11 C10 C4 115.1(2) . . ? C10 O11 Cu1 126.5(2) . 4_665 ? _refine_diff_density_max 0.970 _refine_diff_density_min -0.687 _refine_diff_density_rms 0.121 data_candy3 _database_code_CSD 179662 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common '[Cu(PCA)2]2H2O' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H12 Cu N2 O6' _chemical_formula_weight 343.78 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'C c' _symmetry_cell_setting 'Monoclinic' 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' _cell_length_a 4.9410(2) _cell_length_b 25.0290(10) _cell_length_c 10.9600(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.834(2) _cell_angle_gamma 90.00 _cell_volume 1342.75(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1831 _cell_measurement_theta_min 2.910 _cell_measurement_theta_max 30.034 _exptl_crystal_description Bar _exptl_crystal_colour Blue _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method ? _exptl_crystal_F_000 700 _exptl_absorpt_coefficient_mu 1.656 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.96 _exptl_special_details ; ? ; _diffrn_measurement_device 'KappaCCD' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71070 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method 'CCD' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3592 _diffrn_reflns_av_R_equivalents 0.036 diffrn_reflns_av_sigmaI/netI 0.0737 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 30.04 _diffrn_orient_matrix_type 'X=UH' _diffrn_orient_matrix_UB_11 0.17688 _diffrn_orient_matrix_UB_12 0.10211 _diffrn_orient_matrix_UB_13 -0.00536 _diffrn_orient_matrix_UB_21 0.00207 _diffrn_orient_matrix_UB_22 -0.00566 _diffrn_orient_matrix_UB_23 -0.03950 _diffrn_orient_matrix_UB_31 -0.03455 _diffrn_orient_matrix_UB_32 0.08424 _diffrn_orient_matrix_UB_33 -0.01388 _reflns_number_total 1880 _reflns_number_observed 1594 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'KappaCCD' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 19 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0106P)^2^+2.5446P] 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 ? _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 0.09(2) _refine_ls_number_reflns 1861 _refine_ls_number_parameters 190 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0626 _refine_ls_R_factor_obs 0.0449 _refine_ls_wR_factor_all 0.0889 _refine_ls_wR_factor_obs 0.0730 _refine_ls_goodness_of_fit_all 1.057 _refine_ls_goodness_of_fit_obs 1.075 _refine_ls_restrained_S_all 1.198 _refine_ls_restrained_S_obs 1.074 _refine_ls_shift/esd_max -0.007 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.50262(11) 0.11321(2) 0.44296(8) 0.01126(13) Uani 1 d . . N1 N 0.6586(11) 0.1741(2) 0.5497(5) 0.0115(12) Uani 1 d . . C10 C 0.9409(13) 0.3167(3) 0.7465(6) 0.0141(13) Uani 1 d . . O1 O 0.8214(9) 0.3293(2) 0.8375(4) 0.0147(11) Uani 1 d . . O2 O 1.1402(7) 0.34147(14) 0.7145(4) 0.0234(9) Uani 1 d . . C12 C 0.5527(14) 0.1890(3) 0.6519(6) 0.0159(14) Uani 1 d . . H12A H 0.4200(14) 0.1676(3) 0.6799(6) 0.019 Uiso 1 calc R . C13 C 0.6364(13) 0.2353(3) 0.7163(7) 0.0172(14) Uani 1 d . . H13A H 0.5594(13) 0.2448(3) 0.7860(7) 0.021 Uiso 1 calc R . C14 C 0.8350(13) 0.2672(3) 0.6759(6) 0.0147(13) Uani 1 d . . C15 C 0.9471(11) 0.2519(2) 0.5714(4) 0.0154(11) Uani 1 d . . H15A H 1.0826(11) 0.2723(2) 0.5428(4) 0.018 Uiso 1 calc R . C16 C 0.8522(10) 0.2056(2) 0.5110(4) 0.0141(10) Uani 1 d . . H16A H 0.9252(10) 0.1957(2) 0.4405(4) 0.017 Uiso 1 calc R . N2 N 0.3468(9) 0.0558(2) 0.3253(4) 0.0130(11) Uani 1 d . . C20 C -0.0055(10) -0.0663(2) 0.0744(5) 0.0132(10) Uani 1 d . . O3 O -0.2596(8) -0.0602(2) 0.0369(4) 0.0142(9) Uani 1 d . . O4 O 0.1449(7) -0.10337(13) 0.0483(3) 0.0142(8) Uani 1 d . . C22 C 0.1148(11) 0.0645(2) 0.2488(5) 0.0184(11) Uani 1 d . . H22A H 0.0310(11) 0.0977(2) 0.2504(5) 0.022 Uiso 1 calc R . C23 C -0.0046(11) 0.0264(2) 0.1680(5) 0.0168(11) Uani 1 d . . H23A H -0.1676(11) 0.0339(2) 0.1179(5) 0.020 Uiso 1 calc R . C24 C 0.1179(10) -0.0232(2) 0.1613(4) 0.0124(10) Uani 1 d . . C25 C 0.3587(10) -0.0323(2) 0.2394(5) 0.0176(11) Uani 1 d . . H25A H 0.4490(10) -0.0648(2) 0.2368(5) 0.021 Uiso 1 calc R . C26 C 0.4648(11) 0.0068(2) 0.3212(5) 0.0170(11) Uani 1 d . . H26A H 0.6222(11) -0.0006(2) 0.3754(5) 0.020 Uiso 1 calc R . O1W O -0.3636(10) 0.1190(2) -0.0286(5) 0.0499(13) Uani 1 d . . H1W H -0.5008(10) 0.1311(2) -0.0756(5) 0.075 Uiso 1 d R . H2W H -0.3590(10) 0.1340(2) 0.0412(5) 0.075 Uiso 1 d R . O2W O 0.0971(11) 0.1429(3) -0.1350(6) 0.067(2) Uani 1 d . . H3W H -0.0412(11) 0.1359(3) -0.0994(6) 0.100 Uiso 1 d R . H4WA H 0.0840(11) 0.1760(3) -0.1518(6) 0.100 Uiso 0.50 d PR . H4WB H 0.0676(11) 0.1267(3) -0.2038(6) 0.100 Uiso 0.50 d PR . 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 Cu1 0.0132(3) 0.0078(2) 0.0116(2) -0.0006(4) -0.0024(2) 0.0000(4) N1 0.013(3) 0.009(3) 0.011(3) -0.002(2) -0.004(2) 0.000(2) C10 0.014(3) 0.010(3) 0.016(3) 0.005(2) -0.005(3) -0.001(2) O1 0.021(3) 0.011(2) 0.012(2) 0.001(2) 0.001(2) -0.001(2) O2 0.024(2) 0.023(2) 0.025(2) -0.010(2) 0.008(2) -0.011(2) C12 0.018(3) 0.016(3) 0.013(3) -0.001(2) 0.003(3) -0.001(2) C13 0.014(3) 0.017(3) 0.022(3) 0.000(3) 0.004(3) -0.001(2) C14 0.013(3) 0.014(3) 0.014(3) -0.003(2) -0.007(3) 0.003(2) C15 0.022(3) 0.013(2) 0.012(2) -0.001(2) 0.004(2) 0.000(2) C16 0.017(3) 0.013(2) 0.013(2) -0.001(2) 0.003(2) 0.000(2) N2 0.015(3) 0.013(2) 0.011(2) -0.001(2) 0.001(2) -0.003(2) C20 0.018(3) 0.011(2) 0.010(2) -0.001(2) 0.000(2) 0.002(2) O3 0.013(2) 0.010(2) 0.018(2) -0.001(2) -0.005(2) -0.001(2) O4 0.016(2) 0.011(2) 0.016(2) -0.0045(13) 0.004(2) 0.0011(13) C22 0.016(3) 0.017(2) 0.020(3) -0.001(2) -0.005(2) 0.008(2) C23 0.016(3) 0.014(2) 0.017(3) -0.002(2) -0.010(2) 0.000(2) C24 0.015(3) 0.010(2) 0.011(2) -0.001(2) -0.002(2) 0.001(2) C25 0.016(3) 0.013(2) 0.023(3) -0.004(2) -0.001(2) 0.004(2) C26 0.018(3) 0.014(2) 0.016(3) 0.000(2) -0.005(2) 0.003(2) O1W 0.048(3) 0.059(3) 0.042(3) -0.012(2) 0.000(2) 0.018(2) O2W 0.042(3) 0.091(5) 0.069(4) 0.005(4) 0.009(3) 0.015(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 Cu1 O3 1.967(4) 2_655 ? Cu1 O1 1.981(5) 4_454 ? Cu1 N1 2.009(5) . ? Cu1 N2 2.013(5) . ? Cu1 O4 2.252(3) 2 ? N1 C16 1.352(7) . ? N1 C12 1.351(8) . ? C10 O2 1.254(7) . ? C10 O1 1.267(8) . ? C10 C14 1.515(9) . ? O1 Cu1 1.981(5) 4 ? C12 C13 1.391(9) . ? C13 C14 1.384(6) . ? C14 C15 1.392(8) . ? C15 C16 1.384(6) . ? N2 C22 1.342(7) . ? N2 C26 1.360(7) . ? C20 O4 1.246(6) . ? C20 O3 1.276(6) . ? C20 C24 1.512(7) . ? O3 Cu1 1.967(4) 2_454 ? O4 Cu1 2.252(3) 2_554 ? C22 C23 1.378(7) . ? C23 C24 1.387(6) . ? C24 C25 1.387(7) . ? C25 C26 1.382(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 O3 Cu1 O1 170.1(2) 2_655 4_454 ? O3 Cu1 N1 93.0(2) 2_655 . ? O1 Cu1 N1 84.03(13) 4_454 . ? O3 Cu1 N2 90.15(14) 2_655 . ? O1 Cu1 N2 92.4(2) 4_454 . ? N1 Cu1 N2 175.8(2) . . ? O3 Cu1 O4 96.48(14) 2_655 2 ? O1 Cu1 O4 93.12(15) 4_454 2 ? N1 Cu1 O4 92.9(2) . 2 ? N2 Cu1 O4 89.5(2) . 2 ? C16 N1 C12 118.0(5) . . ? C16 N1 Cu1 119.5(4) . . ? C12 N1 Cu1 122.0(5) . . ? O2 C10 O1 124.4(6) . . ? O2 C10 C14 119.4(6) . . ? O1 C10 C14 116.2(6) . . ? C10 O1 Cu1 114.7(4) . 4 ? N1 C12 C13 121.9(6) . . ? C14 C13 C12 119.6(5) . . ? C13 C14 C15 118.9(5) . . ? C13 C14 C10 121.2(5) . . ? C15 C14 C10 119.8(6) . . ? C16 C15 C14 118.5(5) . . ? N1 C16 C15 123.2(5) . . ? C22 N2 C26 117.3(5) . . ? C22 N2 Cu1 120.3(4) . . ? C26 N2 Cu1 122.4(4) . . ? O4 C20 O3 127.4(5) . . ? O4 C20 C24 118.3(4) . . ? O3 C20 C24 114.3(4) . . ? C20 O3 Cu1 125.4(3) . 2_454 ? C20 O4 Cu1 137.2(3) . 2_554 ? N2 C22 C23 122.9(5) . . ? C22 C23 C24 120.1(5) . . ? C23 C24 C25 117.2(4) . . ? C23 C24 C20 122.1(4) . . ? C25 C24 C20 120.7(4) . . ? C26 C25 C24 120.2(5) . . ? N2 C26 C25 122.2(5) . . ? _refine_diff_density_max 0.420 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.106 data_candy5 _database_code_CSD 179663 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common '[Cu(PCA)2(H2O)4]' _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H16 Cu N2 O8' _chemical_formula_weight 379.80 _chemical_melting_point ? _chemical_compound_source ? 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' 'Cu' 'Cu' 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.357(2) _cell_length_b 6.926(2) _cell_length_c 9.213(3) _cell_angle_alpha 99.42(2) _cell_angle_beta 105.36(2) _cell_angle_gamma 108.14(2) _cell_volume 358.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Bar _exptl_crystal_colour Turquoise-green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method ? _exptl_crystal_F_000 195 _exptl_absorpt_coefficient_mu 1.572 _exptl_absorpt_correction_type 'Semi-empirical (Psi scans)' _exptl_absorpt_correction_T_min 0.85 _exptl_absorpt_correction_T_max 0.95 _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1374 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0724 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1249 _reflns_number_observed 956 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 12 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+1.0000P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1237 _refine_ls_number_parameters 106 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_obs 0.0625 _refine_ls_wR_factor_all 0.2113 _refine_ls_wR_factor_obs 0.1465 _refine_ls_goodness_of_fit_all 1.093 _refine_ls_goodness_of_fit_obs 1.090 _refine_ls_restrained_S_all 1.367 _refine_ls_restrained_S_obs 1.090 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.5000 0.0293(4) Uani 1 d S . N1 N 0.2675(9) 0.3752(8) 0.2821(6) 0.0265(13) Uani 1 d . . C2 C 0.0333(12) 0.2983(11) 0.2516(8) 0.032(2) Uani 1 d . . H2A H -0.0229(12) 0.2945(11) 0.3350(8) 0.038 Uiso 1 calc R . C3 C -0.1264(12) 0.2251(11) 0.1019(7) 0.030(2) Uani 1 d . . H3A H -0.2867(12) 0.1735(11) 0.0859(7) 0.036 Uiso 1 calc R . C4 C -0.0483(11) 0.2283(10) -0.0249(7) 0.0257(14) Uani 1 d . . C5 C 0.1948(12) 0.3016(10) 0.0069(7) 0.029(2) Uani 1 d . . H5A H 0.2551(12) 0.3023(10) -0.0747(7) 0.035 Uiso 1 calc R . C6 C 0.3443(12) 0.3724(11) 0.1590(7) 0.030(2) Uani 1 d . . H6A H 0.5055(12) 0.4206(11) 0.1778(7) 0.036 Uiso 1 calc R . C10 C -0.2130(12) 0.1592(11) -0.1914(8) 0.031(2) Uani 1 d . . O11 O -0.4288(9) 0.0601(9) -0.2139(6) 0.0431(13) Uani 1 d . . O12 O -0.1282(9) 0.2013(9) -0.2941(5) 0.0415(13) Uani 1 d . . O1W O 0.3466(7) 0.7049(7) 0.5408(5) 0.0313(11) Uani 1 d . . H1W H 0.3189(7) 0.7562(7) 0.4632(5) 0.038 Uiso 1 d R . H2W H 0.4385(7) 0.8056(7) 0.6210(5) 0.038 Uiso 1 d R . O2W O 0.2516(9) 0.2314(8) 0.5927(6) 0.0457(14) Uani 1 d . . H3W H 0.2003(9) 0.2866(8) 0.6581(6) 0.055 Uiso 1 d R . H4W H 0.3263(9) 0.1604(8) 0.6339(6) 0.055 Uiso 1 d R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0260(7) 0.0383(8) 0.0167(6) 0.0003(5) -0.0017(5) 0.0139(6) N1 0.029(3) 0.030(3) 0.017(3) 0.001(2) 0.005(2) 0.012(2) C2 0.026(4) 0.041(4) 0.023(3) -0.001(3) 0.006(3) 0.012(3) C3 0.024(3) 0.038(4) 0.023(3) 0.003(3) 0.003(3) 0.011(3) C4 0.028(4) 0.021(3) 0.021(3) 0.003(3) 0.000(3) 0.008(3) C5 0.033(4) 0.031(4) 0.020(3) 0.009(3) 0.007(3) 0.009(3) C6 0.026(4) 0.034(4) 0.024(3) 0.006(3) 0.001(3) 0.013(3) C10 0.031(4) 0.028(4) 0.025(3) 0.000(3) -0.004(3) 0.011(3) O11 0.031(3) 0.050(3) 0.032(3) 0.007(2) -0.006(2) 0.010(3) O12 0.035(3) 0.065(4) 0.023(3) 0.010(2) 0.003(2) 0.023(3) O1W 0.025(2) 0.046(3) 0.019(2) 0.005(2) -0.003(2) 0.018(2) O2W 0.037(3) 0.054(4) 0.047(3) 0.016(3) 0.009(3) 0.021(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 Cu1 O1W 1.997(5) 2_666 ? Cu1 O1W 1.997(5) . ? Cu1 N1 2.006(5) 2_666 ? Cu1 N1 2.006(5) . ? N1 C2 1.347(8) . ? N1 C6 1.349(8) . ? C2 C3 1.378(9) . ? C3 C4 1.385(9) . ? C4 C5 1.398(10) . ? C4 C10 1.508(8) . ? C5 C6 1.373(9) . ? C10 O12 1.239(9) . ? C10 O11 1.270(9) . ? 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 O1W Cu1 O1W 179.998(2) 2_666 . ? O1W Cu1 N1 90.0(2) 2_666 2_666 ? O1W Cu1 N1 90.0(2) . 2_666 ? O1W Cu1 N1 90.0(2) 2_666 . ? O1W Cu1 N1 90.0(2) . . ? N1 Cu1 N1 180.0 2_666 . ? C2 N1 C6 117.4(5) . . ? C2 N1 Cu1 122.8(4) . . ? C6 N1 Cu1 119.8(4) . . ? N1 C2 C3 122.7(6) . . ? C2 C3 C4 120.1(6) . . ? C3 C4 C5 117.1(6) . . ? C3 C4 C10 122.9(6) . . ? C5 C4 C10 120.0(6) . . ? C6 C5 C4 119.8(6) . . ? N1 C6 C5 122.8(6) . . ? O12 C10 O11 125.5(6) . . ? O12 C10 C4 118.1(6) . . ? O11 C10 C4 116.4(6) . . ? _refine_diff_density_max 0.473 _refine_diff_density_min -0.501 _refine_diff_density_rms 0.125