Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Li-Min Zheng' 'Wen-Xin Du' 'Yi-Zhi Li' 'Yun-Sheng Ma' 'You Song' _publ_contact_author_name 'Li-Min Zheng' _publ_contact_author_address ; Coordination Chemistry Institute Nanjing University Nanjing 210093 CHINA ; _publ_contact_author_email LMZHENG@NETRA.NJU.EDU.CN _publ_requested_journal 'Dalton Transactions' _publ_section_title ; Dinuclear and layered copper 2-pyridylphosphonates with weak ferromagnetism observed in layer compound Cu(C5H4NPO3). ; # Attachment 'cu1-p.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 292202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H10 Cu N2 O6 P2' _chemical_formula_sum 'C10 H10 Cu N2 O6 P2' _chemical_formula_weight 379.68 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' P P 0.1023 0.0942 '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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4045(19) _cell_length_b 8.751(2) _cell_length_c 10.632(2) _cell_angle_alpha 66.673(4) _cell_angle_beta 72.566(4) _cell_angle_gamma 70.690(4) _cell_volume 664.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 894 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 24.29 _exptl_crystal_description neddle _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 1.912 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.91 _exptl_absorpt_correction_T_max 0.96 _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 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 3318 _diffrn_reflns_av_R_equivalents 0.0864 _diffrn_reflns_av_sigmaI/netI 0.1004 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2295 _reflns_number_gt 1830 _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^)+(0.0476P)^2^] 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 2295 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1400 _refine_ls_wR_factor_gt 0.1320 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _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 Cu1 Cu 0.49307(10) 0.30963(9) 0.46999(8) 0.0283(3) Uani 1 1 d . . . N1 N 0.3369(7) 0.4644(6) 0.3389(5) 0.0284(12) Uani 1 1 d . . . N2 N 0.6556(6) 0.1444(6) 0.5950(5) 0.0259(11) Uani 1 1 d . . . O1 O 0.6441(6) 0.4703(5) 0.3662(4) 0.0332(11) Uani 1 1 d . . . O2 O 0.7324(6) 0.4201(6) 0.1335(5) 0.0392(12) Uani 1 1 d . . . H2B H 0.7028 0.3259 0.1791 0.059 Uiso 1 1 d R . . O3 O 0.6834(7) 0.7148(6) 0.1301(4) 0.0413(12) Uani 1 1 d . . . O4 O 0.3292(5) 0.1718(5) 0.5796(4) 0.0314(10) Uani 1 1 d . . . O5 O 0.3712(6) -0.1525(5) 0.6959(4) 0.0372(11) Uani 1 1 d . . . O6 O 0.2759(6) 0.0298(5) 0.8428(4) 0.0338(11) Uani 1 1 d . . . H6C H 0.2818 0.1223 0.8479 0.051 Uiso 1 1 d R . . P1 P 0.6318(2) 0.5511(2) 0.21262(16) 0.0286(4) Uani 1 1 d . . . P2 P 0.3805(2) 0.0121(2) 0.69971(16) 0.0257(4) Uani 1 1 d . . . C1 C 0.4057(8) 0.5767(8) 0.2214(6) 0.0297(14) Uani 1 1 d . . . C2 C 0.3119(10) 0.6930(9) 0.1223(7) 0.0421(18) Uani 1 1 d . . . H2 H 0.3623 0.7690 0.0426 0.051 Uiso 1 1 calc R . . C3 C 0.1420(10) 0.6946(10) 0.1438(8) 0.052(2) Uani 1 1 d . . . H3 H 0.0755 0.7728 0.0786 0.062 Uiso 1 1 calc R . . C4 C 0.0699(10) 0.5789(9) 0.2632(8) 0.0457(18) Uani 1 1 d . . . H4 H -0.0447 0.5776 0.2788 0.055 Uiso 1 1 calc R . . C5 C 0.1717(9) 0.4669(9) 0.3572(7) 0.0366(16) Uani 1 1 d . . . H5 H 0.1240 0.3891 0.4371 0.044 Uiso 1 1 calc R . . C6 C 0.6012(8) 0.0080(8) 0.6923(6) 0.0283(14) Uani 1 1 d . . . C7 C 0.7045(9) -0.1205(9) 0.7805(7) 0.0412(17) Uani 1 1 d . . . H7 H 0.6644 -0.2134 0.8483 0.049 Uiso 1 1 calc R . . C8 C 0.8679(10) -0.1076(10) 0.7655(8) 0.049(2) Uani 1 1 d . . . H8 H 0.9400 -0.1922 0.8239 0.059 Uiso 1 1 calc R . . C9 C 0.9249(9) 0.0294(10) 0.6648(8) 0.0461(19) Uani 1 1 d . . . H9 H 1.0363 0.0382 0.6525 0.055 Uiso 1 1 calc R . . C10 C 0.8143(9) 0.1533(9) 0.5825(7) 0.0376(16) Uani 1 1 d . . . H10 H 0.8521 0.2477 0.5151 0.045 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 Cu1 0.0262(5) 0.0268(4) 0.0278(4) 0.0006(3) -0.0117(3) -0.0072(3) N1 0.027(3) 0.029(3) 0.026(3) -0.006(2) -0.009(2) -0.003(2) N2 0.022(3) 0.028(3) 0.022(3) -0.006(2) -0.005(2) -0.001(2) O1 0.037(3) 0.036(3) 0.031(2) -0.004(2) -0.012(2) -0.016(2) O2 0.036(3) 0.039(3) 0.038(3) -0.015(2) 0.006(2) -0.012(2) O3 0.057(3) 0.036(3) 0.032(3) -0.010(2) -0.001(2) -0.022(2) O4 0.022(2) 0.033(2) 0.035(3) -0.001(2) -0.011(2) -0.0087(19) O5 0.040(3) 0.036(3) 0.034(3) -0.009(2) -0.008(2) -0.011(2) O6 0.039(3) 0.030(2) 0.030(2) -0.0085(19) -0.004(2) -0.009(2) P1 0.0351(10) 0.0272(9) 0.0237(9) -0.0070(7) -0.0039(7) -0.0112(7) P2 0.0261(9) 0.0232(8) 0.0248(8) -0.0050(7) -0.0066(7) -0.0043(7) C1 0.029(4) 0.030(3) 0.029(3) -0.010(3) -0.013(3) 0.002(3) C2 0.049(5) 0.038(4) 0.023(3) 0.000(3) -0.010(3) -0.001(3) C3 0.042(5) 0.060(5) 0.041(5) -0.010(4) -0.022(4) 0.008(4) C4 0.031(4) 0.055(5) 0.050(5) -0.018(4) -0.020(4) 0.003(3) C5 0.031(4) 0.038(4) 0.038(4) -0.009(3) -0.008(3) -0.009(3) C6 0.025(4) 0.033(4) 0.028(3) -0.012(3) -0.006(3) -0.006(3) C7 0.042(4) 0.039(4) 0.034(4) -0.001(3) -0.016(3) -0.005(3) C8 0.036(5) 0.055(5) 0.047(5) -0.009(4) -0.026(4) 0.007(4) C9 0.020(4) 0.066(5) 0.054(5) -0.023(4) -0.015(4) 0.000(4) C10 0.031(4) 0.046(4) 0.038(4) -0.018(3) -0.004(3) -0.009(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 O4 1.932(4) . ? Cu1 O1 1.979(4) . ? Cu1 N1 1.981(5) . ? Cu1 N2 1.996(5) . ? N1 C5 1.337(8) . ? N1 C1 1.353(8) . ? N2 C10 1.326(8) . ? N2 C6 1.343(7) . ? O1 P1 1.522(4) . ? O2 P1 1.561(5) . ? O2 H2B 0.8500 . ? O3 P1 1.483(4) . ? O4 P2 1.512(4) . ? O5 P2 1.485(4) . ? O6 P2 1.551(4) . ? O6 H6C 0.8500 . ? P1 C1 1.816(7) . ? P2 C6 1.822(6) . ? C1 C2 1.372(8) . ? C2 C3 1.373(10) . ? C2 H2 0.9300 . ? C3 C4 1.389(11) . ? C3 H3 0.9300 . ? C4 C5 1.369(9) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.381(9) . ? C7 C8 1.371(10) . ? C7 H7 0.9300 . ? C8 C9 1.368(10) . ? C8 H8 0.9300 . ? C9 C10 1.369(9) . ? C9 H9 0.9300 . ? 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 O4 Cu1 O1 173.80(19) . . ? O4 Cu1 N1 92.05(19) . . ? O1 Cu1 N1 86.05(19) . . ? O4 Cu1 N2 87.74(19) . . ? O1 Cu1 N2 94.51(19) . . ? N1 Cu1 N2 176.5(2) . . ? C5 N1 C1 118.1(5) . . ? C5 N1 Cu1 125.7(5) . . ? C1 N1 Cu1 116.2(4) . . ? C10 N2 C6 118.6(6) . . ? C10 N2 Cu1 125.2(4) . . ? C6 N2 Cu1 116.0(4) . . ? P1 O1 Cu1 111.6(2) . . ? P1 O2 H2B 108.9 . . ? P2 O4 Cu1 119.0(2) . . ? P2 O6 H6C 109.0 . . ? O3 P1 O1 119.1(2) . . ? O3 P1 O2 107.9(3) . . ? O1 P1 O2 110.5(3) . . ? O3 P1 C1 111.0(3) . . ? O1 P1 C1 101.7(3) . . ? O2 P1 C1 105.8(3) . . ? O5 P2 O4 117.0(2) . . ? O5 P2 O6 107.6(2) . . ? O4 P2 O6 111.8(2) . . ? O5 P2 C6 110.5(3) . . ? O4 P2 C6 102.8(3) . . ? O6 P2 C6 106.7(3) . . ? N1 C1 C2 122.5(6) . . ? N1 C1 P1 111.9(4) . . ? C2 C1 P1 125.6(5) . . ? C1 C2 C3 118.4(7) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? C2 C3 C4 119.8(7) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.3(7) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 122.8(7) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? N2 C6 C7 121.9(6) . . ? N2 C6 P2 114.2(5) . . ? C7 C6 P2 123.8(5) . . ? C8 C7 C6 118.2(7) . . ? C8 C7 H7 120.9 . . ? C6 C7 H7 120.9 . . ? C9 C8 C7 120.1(7) . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 118.5(7) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? N2 C10 C9 122.7(7) . . ? N2 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.710 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.119 # Attachment 'cu2f-p.cif' data_Cu3(OH)2(2-pyPO3)2.2H2O _database_code_depnum_ccdc_archive 'CCDC 292203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H14 Cu3 N2 O10 P2' _chemical_formula_weight 574.79 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' P P 0.1023 0.0942 '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 P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.9544(17) _cell_length_b 21.579(4) _cell_length_c 5.0243(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.332(3) _cell_angle_gamma 90.00 _cell_volume 831.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 747 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 25.55 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 4.051 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.32 _exptl_absorpt_correction_T_max 0.38 _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 1000 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 2689 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.03 _reflns_number_total 1456 _reflns_number_gt 1137 _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^)+(0.0556P)^2^+0.7703P] 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 1456 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.1214 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.142 _refine_ls_restrained_S_all 1.142 _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 Cu1 Cu 0.36535(11) 0.54476(4) 0.55941(17) 0.0330(3) Uani 1 1 d . . . Cu2 Cu 0.0000 0.5000 0.5000 0.0385(3) Uani 1 2 d S . . P1 P 0.2680(3) 0.44475(9) 1.0528(4) 0.0416(5) Uani 1 1 d . . . O1 O 0.2175(7) 0.4852(2) 0.7953(10) 0.0418(12) Uani 1 1 d . . . O2 O 0.1251(6) 0.41274(19) 1.1331(10) 0.0335(10) Uani 1 1 d . . . O3 O 0.3871(7) 0.4847(2) 1.2809(11) 0.0485(13) Uani 1 1 d . . . O4 O 0.1333(7) 0.5656(2) 0.3989(11) 0.0464(13) Uani 1 1 d . . . H4A H 0.1135 0.5680 0.2244 0.056 Uiso 1 1 d R . . N1 N 0.5903(10) 0.3905(3) 1.1529(14) 0.0522(17) Uani 1 1 d . . . C1 C 0.4201(11) 0.3904(4) 0.9789(17) 0.0475(19) Uani 1 1 d . . . C2 C 0.3798(10) 0.3514(3) 0.7450(15) 0.0406(17) Uani 1 1 d . . . H2 H 0.2677 0.3511 0.6276 0.049 Uiso 1 1 calc R . . C3 C 0.5074(10) 0.3136(4) 0.6905(17) 0.0468(18) Uani 1 1 d . . . H3 H 0.4812 0.2876 0.5375 0.056 Uiso 1 1 calc R . . C4 C 0.6748(11) 0.3148(3) 0.8658(16) 0.0440(18) Uani 1 1 d . . . H4 H 0.7607 0.2896 0.8281 0.053 Uiso 1 1 calc R . . C5 C 0.7152(11) 0.3525(4) 1.094(2) 0.053(2) Uani 1 1 d . . . H5 H 0.8278 0.3525 1.2099 0.064 Uiso 1 1 calc R . . O1W O 0.1185(7) 0.2834(2) 0.1633(11) 0.0479(13) Uani 1 1 d . . . H1WB H 0.0313 0.2649 0.1944 0.057 Uiso 1 1 d R . . H1WC H 0.0835 0.3090 0.0316 0.057 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0413(5) 0.0276(4) 0.0315(5) 0.0011(3) 0.0120(4) 0.0024(4) Cu2 0.0405(7) 0.0370(7) 0.0383(7) -0.0005(5) 0.0112(6) -0.0014(5) P1 0.0494(12) 0.0403(10) 0.0385(11) 0.0010(8) 0.0178(10) -0.0030(9) O1 0.051(3) 0.041(3) 0.028(3) 0.000(2) 0.001(2) 0.006(2) O2 0.044(3) 0.023(2) 0.034(2) 0.0015(19) 0.012(2) 0.003(2) O3 0.050(3) 0.047(3) 0.049(3) 0.006(3) 0.013(3) -0.007(3) O4 0.048(3) 0.043(3) 0.047(3) -0.006(2) 0.010(3) 0.002(2) N1 0.061(4) 0.052(4) 0.047(4) -0.008(3) 0.021(4) -0.002(3) C1 0.055(5) 0.039(4) 0.043(4) 0.002(3) 0.005(4) 0.010(4) C2 0.053(5) 0.035(4) 0.032(4) 0.002(3) 0.009(3) 0.015(4) C3 0.048(5) 0.052(5) 0.044(4) -0.007(4) 0.017(4) -0.009(4) C4 0.055(5) 0.040(4) 0.044(4) -0.006(3) 0.025(4) 0.005(3) C5 0.051(5) 0.046(4) 0.065(6) 0.012(4) 0.021(4) 0.006(4) O1W 0.049(3) 0.040(3) 0.054(3) -0.003(2) 0.011(3) -0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.863(5) . ? Cu1 O3 1.949(6) 1_554 ? Cu1 N1 1.974(7) 3_667 ? Cu1 O3 2.022(6) 3_667 ? Cu1 O1 2.275(5) . ? Cu1 Cu2 3.0015(10) . ? Cu1 Cu1 3.0583(17) 3_666 ? Cu2 O4 1.917(5) 3_566 ? Cu2 O4 1.917(5) . ? Cu2 O1 1.984(5) 3_566 ? Cu2 O1 1.984(5) . ? Cu2 Cu1 3.0015(10) 3_566 ? P1 O2 1.474(5) . ? P1 O1 1.524(5) . ? P1 O3 1.542(6) . ? P1 C1 1.793(8) . ? O3 Cu1 1.949(6) 1_556 ? O3 Cu1 2.022(6) 3_667 ? N1 C5 1.378(11) . ? N1 C1 1.404(10) . ? N1 Cu1 1.974(7) 3_667 ? C1 C2 1.411(11) . ? C2 C3 1.385(11) . ? C3 C4 1.389(11) . ? C4 C5 1.374(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 Cu1 O3 96.7(2) . 1_554 ? O4 Cu1 N1 96.3(3) . 3_667 ? O3 Cu1 N1 164.6(3) 1_554 3_667 ? O4 Cu1 O3 175.4(2) . 3_667 ? O3 Cu1 O3 79.3(2) 1_554 3_667 ? N1 Cu1 O3 88.0(3) 3_667 3_667 ? O4 Cu1 O1 76.9(2) . . ? O3 Cu1 O1 98.88(19) 1_554 . ? N1 Cu1 O1 92.0(2) 3_667 . ? O3 Cu1 O1 101.5(2) 3_667 . ? O4 Cu1 Cu2 38.06(17) . . ? O3 Cu1 Cu2 88.97(16) 1_554 . ? N1 Cu1 Cu2 106.3(2) 3_667 . ? O3 Cu1 Cu2 138.95(15) 3_667 . ? O1 Cu1 Cu2 41.38(12) . . ? O4 Cu1 Cu1 137.12(17) . 3_666 ? O3 Cu1 Cu1 40.50(16) 1_554 3_666 ? N1 Cu1 Cu1 126.3(2) 3_667 3_666 ? O3 Cu1 Cu1 38.77(16) 3_667 3_666 ? O1 Cu1 Cu1 103.31(13) . 3_666 ? Cu2 Cu1 Cu1 119.15(4) . 3_666 ? O4 Cu2 O4 180.0(2) 3_566 . ? O4 Cu2 O1 83.3(2) 3_566 3_566 ? O4 Cu2 O1 96.7(2) . 3_566 ? O4 Cu2 O1 96.7(2) 3_566 . ? O4 Cu2 O1 83.3(2) . . ? O1 Cu2 O1 180.000(1) 3_566 . ? O4 Cu2 Cu1 36.82(16) 3_566 3_566 ? O4 Cu2 Cu1 143.18(16) . 3_566 ? O1 Cu2 Cu1 49.29(15) 3_566 3_566 ? O1 Cu2 Cu1 130.71(15) . 3_566 ? O4 Cu2 Cu1 143.18(16) 3_566 . ? O4 Cu2 Cu1 36.82(15) . . ? O1 Cu2 Cu1 130.71(15) 3_566 . ? O1 Cu2 Cu1 49.29(15) . . ? Cu1 Cu2 Cu1 180.00(3) 3_566 . ? O2 P1 O1 116.8(3) . . ? O2 P1 O3 115.1(3) . . ? O1 P1 O3 106.5(3) . . ? O2 P1 C1 111.2(3) . . ? O1 P1 C1 103.9(3) . . ? O3 P1 C1 101.7(4) . . ? P1 O1 Cu2 135.1(3) . . ? P1 O1 Cu1 135.2(3) . . ? Cu2 O1 Cu1 89.33(19) . . ? P1 O3 Cu1 138.7(4) . 1_556 ? P1 O3 Cu1 117.5(3) . 3_667 ? Cu1 O3 Cu1 100.7(2) 1_556 3_667 ? Cu1 O4 Cu2 105.1(3) . . ? C5 N1 C1 119.8(7) . . ? C5 N1 Cu1 125.3(6) . 3_667 ? C1 N1 Cu1 114.4(5) . 3_667 ? N1 C1 C2 119.2(7) . . ? N1 C1 P1 117.6(6) . . ? C2 C1 P1 123.0(6) . . ? C3 C2 C1 119.9(8) . . ? C2 C3 C4 119.6(7) . . ? C5 C4 C3 120.9(7) . . ? C4 C5 N1 120.6(8) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 Cu1 Cu2 O4 180.0 . . . 3_566 ? O3 Cu1 Cu2 O4 77.8(3) 1_554 . . 3_566 ? N1 Cu1 Cu2 O4 -100.8(3) 3_667 . . 3_566 ? O3 Cu1 Cu2 O4 5.5(4) 3_667 . . 3_566 ? O1 Cu1 Cu2 O4 -26.9(3) . . . 3_566 ? Cu1 Cu1 Cu2 O4 49.5(3) 3_666 . . 3_566 ? O3 Cu1 Cu2 O4 -102.2(3) 1_554 . . . ? N1 Cu1 Cu2 O4 79.2(3) 3_667 . . . ? O3 Cu1 Cu2 O4 -174.5(4) 3_667 . . . ? O1 Cu1 Cu2 O4 153.1(3) . . . . ? Cu1 Cu1 Cu2 O4 -130.5(3) 3_666 . . . ? O4 Cu1 Cu2 O1 26.9(3) . . . 3_566 ? O3 Cu1 Cu2 O1 -75.3(2) 1_554 . . 3_566 ? N1 Cu1 Cu2 O1 106.1(3) 3_667 . . 3_566 ? O3 Cu1 Cu2 O1 -147.6(3) 3_667 . . 3_566 ? O1 Cu1 Cu2 O1 180.0 . . . 3_566 ? Cu1 Cu1 Cu2 O1 -103.54(19) 3_666 . . 3_566 ? O4 Cu1 Cu2 O1 -153.1(3) . . . . ? O3 Cu1 Cu2 O1 104.7(2) 1_554 . . . ? N1 Cu1 Cu2 O1 -73.9(3) 3_667 . . . ? O3 Cu1 Cu2 O1 32.4(3) 3_667 . . . ? Cu1 Cu1 Cu2 O1 76.46(19) 3_666 . . . ? O4 Cu1 Cu2 Cu1 0(100) . . . 3_566 ? O3 Cu1 Cu2 Cu1 0(100) 1_554 . . 3_566 ? N1 Cu1 Cu2 Cu1 0(100) 3_667 . . 3_566 ? O3 Cu1 Cu2 Cu1 0(100) 3_667 . . 3_566 ? O1 Cu1 Cu2 Cu1 0(100) . . . 3_566 ? Cu1 Cu1 Cu2 Cu1 0(100) 3_666 . . 3_566 ? O2 P1 O1 Cu2 -8.4(6) . . . . ? O3 P1 O1 Cu2 -138.7(4) . . . . ? C1 P1 O1 Cu2 114.4(5) . . . . ? O2 P1 O1 Cu1 -179.2(3) . . . . ? O3 P1 O1 Cu1 50.5(5) . . . . ? C1 P1 O1 Cu1 -56.4(5) . . . . ? O4 Cu2 O1 P1 -9.4(5) 3_566 . . . ? O4 Cu2 O1 P1 170.6(5) . . . . ? O1 Cu2 O1 P1 -80(100) 3_566 . . . ? Cu1 Cu2 O1 P1 6.5(5) 3_566 . . . ? Cu1 Cu2 O1 P1 -173.5(5) . . . . ? O4 Cu2 O1 Cu1 164.15(19) 3_566 . . . ? O4 Cu2 O1 Cu1 -15.85(19) . . . . ? O1 Cu2 O1 Cu1 94(100) 3_566 . . . ? Cu1 Cu2 O1 Cu1 180.0 3_566 . . . ? O4 Cu1 O1 P1 -169.8(5) . . . . ? O3 Cu1 O1 P1 95.4(4) 1_554 . . . ? N1 Cu1 O1 P1 -73.8(5) 3_667 . . . ? O3 Cu1 O1 P1 14.6(5) 3_667 . . . ? Cu2 Cu1 O1 P1 173.5(5) . . . . ? Cu1 Cu1 O1 P1 54.3(4) 3_666 . . . ? O4 Cu1 O1 Cu2 16.6(2) . . . . ? O3 Cu1 O1 Cu2 -78.2(2) 1_554 . . . ? N1 Cu1 O1 Cu2 112.7(3) 3_667 . . . ? O3 Cu1 O1 Cu2 -158.9(2) 3_667 . . . ? Cu1 Cu1 O1 Cu2 -119.25(14) 3_666 . . . ? O2 P1 O3 Cu1 -44.7(6) . . . 1_556 ? O1 P1 O3 Cu1 86.5(5) . . . 1_556 ? C1 P1 O3 Cu1 -165.0(5) . . . 1_556 ? O2 P1 O3 Cu1 111.0(3) . . . 3_667 ? O1 P1 O3 Cu1 -117.8(3) . . . 3_667 ? C1 P1 O3 Cu1 -9.3(4) . . . 3_667 ? O3 Cu1 O4 Cu2 79.7(3) 1_554 . . . ? N1 Cu1 O4 Cu2 -108.5(3) 3_667 . . . ? O3 Cu1 O4 Cu2 52(3) 3_667 . . . ? O1 Cu1 O4 Cu2 -17.9(2) . . . . ? Cu1 Cu1 O4 Cu2 77.6(3) 3_666 . . . ? O4 Cu2 O4 Cu1 -11(100) 3_566 . . . ? O1 Cu2 O4 Cu1 -159.8(2) 3_566 . . . ? O1 Cu2 O4 Cu1 20.2(2) . . . . ? Cu1 Cu2 O4 Cu1 180.0 3_566 . . . ? C5 N1 C1 C2 -0.2(11) . . . . ? Cu1 N1 C1 C2 172.1(6) 3_667 . . . ? C5 N1 C1 P1 -175.6(6) . . . . ? Cu1 N1 C1 P1 -3.4(8) 3_667 . . . ? O2 P1 C1 N1 -115.0(6) . . . . ? O1 P1 C1 N1 118.6(6) . . . . ? O3 P1 C1 N1 8.1(7) . . . . ? O2 P1 C1 C2 69.8(8) . . . . ? O1 P1 C1 C2 -56.7(7) . . . . ? O3 P1 C1 C2 -167.1(7) . . . . ? N1 C1 C2 C3 0.4(11) . . . . ? P1 C1 C2 C3 175.5(6) . . . . ? C1 C2 C3 C4 -0.6(12) . . . . ? C2 C3 C4 C5 0.6(12) . . . . ? C3 C4 C5 N1 -0.4(12) . . . . ? C1 N1 C5 C4 0.2(11) . . . . ? Cu1 N1 C5 C4 -171.1(6) 3_667 . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.444 _refine_diff_density_min -0.745 _refine_diff_density_rms 0.120 # Attachment 'cu3f-p.cif' data_Cu(C5H4NPO3) _database_code_depnum_ccdc_archive 'CCDC 292204' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H4 Cu N O3 P' _chemical_formula_weight 220.60 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' P P 0.1023 0.0942 '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 'P2(1)/c ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.7793(11) _cell_length_b 15.319(3) _cell_length_c 8.6022(19) _cell_angle_alpha 90.00 _cell_angle_beta 97.156(4) _cell_angle_gamma 90.00 _cell_volume 624.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1604 _cell_measurement_theta_min 2.659 _cell_measurement_theta_max 28.012 _exptl_crystal_description block _exptl_crystal_colour 'deep blue' _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 3.691 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6368 _exptl_absorpt_correction_T_max 0.9262 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_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 3229 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0335 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1222 _reflns_number_gt 1059 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker 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^)+(0.0441P)^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 SHELXL _refine_ls_extinction_coef 0.0158(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1222 _refine_ls_number_parameters 104 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0314 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0766 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _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 Cu1 Cu 0.5000 1.0000 1.0000 0.01583(19) Uani 1 2 d S . . Cu2 Cu 0.5000 1.0000 0.5000 0.01902(19) Uani 1 2 d S . . P1 P 0.93789(17) 1.01368(5) 0.76926(9) 0.0155(2) Uani 1 1 d . . . N1 N 0.6102(5) 0.89201(15) 0.6197(3) 0.0196(5) Uani 1 1 d . . . O1 O 0.8280(4) 1.05612(13) 0.6134(2) 0.0200(5) Uani 1 1 d . . . O2 O 0.7984(4) 1.05117(12) 0.9044(2) 0.0189(5) Uani 1 1 d . . . O3 O 1.2565(5) 1.01618(13) 0.8017(2) 0.0212(5) Uani 1 1 d . . . C1 C 0.8216(6) 0.90054(18) 0.7386(3) 0.0179(6) Uani 1 1 d . . . C2 C 0.9250(7) 0.8292(2) 0.8239(4) 0.0280(7) Uani 1 1 d . . . H2 H 1.0719 0.8358 0.9047 0.034 Uiso 1 1 calc R . . C3 C 0.8108(8) 0.74770(19) 0.7896(4) 0.0296(8) Uani 1 1 d . . . H3 H 0.8830 0.6988 0.8447 0.036 Uiso 1 1 calc R . . C4 C 0.5883(8) 0.74000(19) 0.6725(4) 0.0301(8) Uani 1 1 d . . . H4 H 0.5031 0.6862 0.6495 0.036 Uiso 1 1 calc R . . C5 C 0.4943(7) 0.81322(19) 0.5901(4) 0.0265(7) Uani 1 1 d . . . H5 H 0.3444 0.8079 0.5107 0.032 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 Cu1 0.0120(3) 0.0187(3) 0.0159(3) 0.00007(18) -0.0022(2) -0.00020(17) Cu2 0.0183(3) 0.0170(3) 0.0192(3) 0.00149(18) -0.0078(2) -0.00173(18) P1 0.0129(4) 0.0164(4) 0.0157(4) 0.0008(3) -0.0039(3) -0.0015(3) N1 0.0179(14) 0.0185(13) 0.0211(12) -0.0004(10) -0.0028(10) -0.0008(10) O1 0.0194(11) 0.0195(11) 0.0192(11) 0.0021(8) -0.0050(8) -0.0044(8) O2 0.0169(10) 0.0202(11) 0.0187(10) -0.0013(8) -0.0007(8) 0.0001(8) O3 0.0153(12) 0.0292(11) 0.0184(11) 0.0014(9) -0.0014(8) -0.0016(8) C1 0.0175(15) 0.0176(15) 0.0183(15) -0.0020(11) 0.0012(12) -0.0006(11) C2 0.0288(18) 0.0265(17) 0.0258(17) -0.0005(13) -0.0087(14) 0.0000(13) C3 0.040(2) 0.0188(17) 0.0283(19) 0.0027(12) -0.0040(16) 0.0030(13) C4 0.035(2) 0.0180(16) 0.035(2) -0.0032(13) -0.0036(17) -0.0040(13) C5 0.0256(17) 0.0234(16) 0.0280(18) -0.0039(13) -0.0065(14) -0.0034(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 Cu1 O2 1.902(2) . ? Cu1 O2 1.902(2) 3_677 ? Cu1 O3 1.958(2) 3_777 ? Cu1 O3 1.958(2) 1_455 ? Cu2 O1 1.9410(19) . ? Cu2 O1 1.9410(19) 3_676 ? Cu2 N1 1.985(2) . ? Cu2 N1 1.985(2) 3_676 ? P1 O3 1.514(2) . ? P1 O2 1.522(2) . ? P1 O1 1.5233(19) . ? P1 C1 1.829(3) . ? N1 C5 1.339(4) . ? N1 C1 1.351(4) . ? O3 Cu1 1.958(2) 1_655 ? C1 C2 1.374(4) . ? C2 C3 1.380(4) . ? C3 C4 1.376(5) . ? C4 C5 1.372(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.00(10) . 3_677 ? O2 Cu1 O3 91.88(9) . 3_777 ? O2 Cu1 O3 88.12(8) 3_677 3_777 ? O2 Cu1 O3 88.12(8) . 1_455 ? O2 Cu1 O3 91.88(9) 3_677 1_455 ? O3 Cu1 O3 180.000(1) 3_777 1_455 ? O1 Cu2 O1 180.0 . 3_676 ? O1 Cu2 N1 87.88(9) . . ? O1 Cu2 N1 92.12(9) 3_676 . ? O1 Cu2 N1 92.12(9) . 3_676 ? O1 Cu2 N1 87.88(9) 3_676 3_676 ? N1 Cu2 N1 180.000(1) . 3_676 ? O3 P1 O2 112.08(12) . . ? O3 P1 O1 112.32(12) . . ? O2 P1 O1 112.03(12) . . ? O3 P1 C1 109.33(13) . . ? O2 P1 C1 108.28(12) . . ? O1 P1 C1 102.24(12) . . ? C5 N1 C1 118.9(2) . . ? C5 N1 Cu2 125.2(2) . . ? C1 N1 Cu2 115.91(19) . . ? P1 O1 Cu2 114.94(11) . . ? P1 O2 Cu1 126.72(12) . . ? P1 O3 Cu1 129.22(13) . 1_655 ? N1 C1 C2 120.8(3) . . ? N1 C1 P1 112.7(2) . . ? C2 C1 P1 126.4(2) . . ? C1 C2 C3 120.0(3) . . ? C4 C3 C2 118.9(3) . . ? C5 C4 C3 118.8(3) . . ? N1 C5 C4 122.5(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu2 N1 C5 -170.3(3) . . . . ? O1 Cu2 N1 C5 9.7(3) 3_676 . . . ? N1 Cu2 N1 C5 -28(100) 3_676 . . . ? O1 Cu2 N1 C1 8.9(2) . . . . ? O1 Cu2 N1 C1 -171.1(2) 3_676 . . . ? N1 Cu2 N1 C1 151(100) 3_676 . . . ? O3 P1 O1 Cu2 143.51(12) . . . . ? O2 P1 O1 Cu2 -89.30(14) . . . . ? C1 P1 O1 Cu2 26.43(15) . . . . ? O1 Cu2 O1 P1 54(100) 3_676 . . . ? N1 Cu2 O1 P1 -22.56(14) . . . . ? N1 Cu2 O1 P1 157.44(14) 3_676 . . . ? O3 P1 O2 Cu1 -132.02(14) . . . . ? O1 P1 O2 Cu1 100.66(15) . . . . ? C1 P1 O2 Cu1 -11.34(18) . . . . ? O2 Cu1 O2 P1 -58(100) 3_677 . . . ? O3 Cu1 O2 P1 114.22(15) 3_777 . . . ? O3 Cu1 O2 P1 -65.78(15) 1_455 . . . ? O2 P1 O3 Cu1 35.29(19) . . . 1_655 ? O1 P1 O3 Cu1 162.46(14) . . . 1_655 ? C1 P1 O3 Cu1 -84.78(18) . . . 1_655 ? C5 N1 C1 C2 2.7(4) . . . . ? Cu2 N1 C1 C2 -176.5(2) . . . . ? C5 N1 C1 P1 -176.3(2) . . . . ? Cu2 N1 C1 P1 4.4(3) . . . . ? O3 P1 C1 N1 -138.7(2) . . . . ? O2 P1 C1 N1 98.9(2) . . . . ? O1 P1 C1 N1 -19.5(2) . . . . ? O3 P1 C1 C2 42.3(3) . . . . ? O2 P1 C1 C2 -80.1(3) . . . . ? O1 P1 C1 C2 161.5(3) . . . . ? N1 C1 C2 C3 -0.7(5) . . . . ? P1 C1 C2 C3 178.3(3) . . . . ? C1 C2 C3 C4 -1.9(5) . . . . ? C2 C3 C4 C5 2.3(5) . . . . ? C1 N1 C5 C4 -2.3(5) . . . . ? Cu2 N1 C5 C4 176.9(2) . . . . ? C3 C4 C5 N1 -0.2(5) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.466 _refine_diff_density_min -0.659 _refine_diff_density_rms 0.117