Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name 'Jamie Manson' 'Urs Geiser' 'Jiyeong Gu' 'Robert Henning' 'Hyun-Joo Koo' 'Jana G. Lecher' ; J.A.Schlueter ; 'Arthur J. Schultz' 'Xiao-ping Wang' 'M. Whangbo' _publ_contact_author_name 'Dr Jamie Manson' _publ_contact_author_address ; Condensed Matter Sciences Division Oak Ridge National Lab P.O. Box 2008 Oak Ridge TN 37831-6430 UNITED STATES OF AMERICA ; _publ_contact_author_email MANSONJL@ORNL.GOV _publ_section_title ; Cu(HCO2)2L {L = pyrazine, 4,4'-bipyridine}: Employing Formate Anion as a Building Block in Three-Dimensional Coordination Polymers ; data_xrays _database_code_CSD 205743 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Cu(HCO2)2(N2C4H4) _chemical_formula_sum 'C6 H6 Cu N2 O4' _chemical_formula_weight 233.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.5799(11) _cell_length_b 7.6759(7) _cell_length_c 8.5592(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.235(5) _cell_angle_gamma 90.00 _cell_volume 760.79(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.040 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 2.851 _exptl_absorpt_correction_type faces _exptl_absorpt_correction_T_min 0.73216 _exptl_absorpt_correction_T_max 0.78962 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2430 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 28.06 _reflns_number_total 859 _reflns_number_gt 817 _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 'ORTEP3 for WINDOWS' _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^)+(0.0561P)^2^+0.8788P] 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 SHELXL _refine_ls_extinction_coef 0.086(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 859 _refine_ls_number_parameters 63 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0325 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.180 _refine_ls_restrained_S_all 1.180 _refine_ls_shift/su_max 0.007 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.2500 0.2500 0.0000 0.0178(3) Uani 1 2 d S . . N1 N 0.1011(2) 0.0978(3) -0.0017(4) 0.0217(5) Uani 1 1 d . . . C1 C -0.0024(3) 0.1732(4) 0.0107(5) 0.0292(7) Uani 1 1 d . . . H1A H -0.0071 0.2938 0.0188 0.035 Uiso 1 1 calc R . . C2 C 0.1029(3) -0.0755(4) -0.0119(6) 0.0326(8) Uani 1 1 d . . . H2A H 0.1736 -0.1323 -0.0199 0.039 Uiso 1 1 calc R . . C3 C 0.3348(3) -0.0324(4) 0.2469(4) 0.0256(6) Uani 1 1 d . . . H3A H 0.3583 0.0442 0.3250 0.031 Uiso 1 1 calc R . . O1 O 0.2883(2) -0.1728(3) 0.2889(3) 0.0275(6) Uani 1 1 d . . . O2 O 0.3518(2) 0.0116(3) 0.1104(3) 0.0273(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0166(3) 0.0151(3) 0.0217(3) -0.00252(15) 0.0015(4) -0.00255(14) N1 0.0183(10) 0.0179(11) 0.0290(13) -0.0014(11) -0.0001(13) -0.0018(8) C1 0.0211(13) 0.0167(13) 0.050(2) -0.0033(13) 0.0003(15) 0.0003(11) C2 0.0189(13) 0.0196(15) 0.059(2) -0.0048(16) 0.0023(17) 0.0012(10) C3 0.0312(15) 0.0224(14) 0.0231(14) -0.0004(13) 0.0005(14) -0.0005(11) O1 0.0359(12) 0.0222(12) 0.0243(11) 0.0021(8) 0.0068(10) -0.0035(10) O2 0.0320(12) 0.0253(11) 0.0246(12) 0.0067(9) 0.0066(10) 0.0028(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 Cu1 O1 1.954(2) 6 ? Cu1 O1 1.954(2) 4 ? Cu1 N1 2.083(2) 7 ? Cu1 N1 2.083(2) . ? Cu1 O2 2.371(2) . ? Cu1 O2 2.371(2) 7 ? N1 C2 1.333(4) . ? N1 C1 1.336(4) . ? C1 C2 1.385(4) 5 ? C2 C1 1.385(4) 5 ? C3 O2 1.233(4) . ? C3 O1 1.258(4) . ? O1 Cu1 1.954(2) 4_545 ? 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 180.0 6 4 ? O1 Cu1 N1 89.19(11) 6 7 ? O1 Cu1 N1 90.81(11) 4 7 ? O1 Cu1 N1 90.81(11) 6 . ? O1 Cu1 N1 89.19(11) 4 . ? N1 Cu1 N1 180.00(7) 7 . ? O1 Cu1 O2 91.15(9) 6 . ? O1 Cu1 O2 88.85(9) 4 . ? N1 Cu1 O2 91.15(9) 7 . ? N1 Cu1 O2 88.85(9) . . ? O1 Cu1 O2 88.85(9) 6 7 ? O1 Cu1 O2 91.15(9) 4 7 ? N1 Cu1 O2 88.85(9) 7 7 ? N1 Cu1 O2 91.15(9) . 7 ? O2 Cu1 O2 180.0 . 7 ? C2 N1 C1 116.9(2) . . ? C2 N1 Cu1 123.2(2) . . ? C1 N1 Cu1 119.96(19) . . ? N1 C1 C2 121.4(3) . 5 ? N1 C2 C1 121.8(3) . 5 ? O2 C3 O1 125.2(3) . . ? C3 O1 Cu1 128.6(2) . 4_545 ? C3 O2 Cu1 120.5(2) . . ? _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 28.06 _diffrn_measured_fraction_theta_full 0.920 _refine_diff_density_max 0.705 _refine_diff_density_min -0.507 _refine_diff_density_rms 0.101 #END data_rtdatam _database_code_CSD 205744 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Cu(HCO2)2(N2C8H10) _chemical_formula_sum 'C12 H10 Cu N2 O4' _chemical_formula_weight 309.76 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 tetragonal _symmetry_space_group_name_H-M P4(1)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+1/4' 'y+1/2, -x+1/2, z+3/4' 'y, x, -z' '-y, -x, -z+1/2' '-x+1/2, y+1/2, -z+1/4' 'x+1/2, -y+1/2, -z+3/4' _cell_length_a 7.8534(2) _cell_length_b 7.8534(2) _cell_length_c 18.4799(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1139.76(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.805 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 628 _exptl_absorpt_coefficient_mu 1.928 _exptl_absorpt_correction_type faces _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7954 _diffrn_reflns_av_R_equivalents 0.0365 _diffrn_reflns_av_sigmaI/netI 0.0234 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1381 _reflns_number_gt 1270 _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 'ORTEP3 for WINDOWS' _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^)+(0.0374P)^2^+0.0832P] 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 0.019(19) _refine_ls_number_reflns 1381 _refine_ls_number_parameters 89 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0267 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0631 _refine_ls_wR_factor_gt 0.0620 _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 0.23734(3) 0.23734(3) 0.0000 0.02062(11) Uani 1 2 d S . . N1 N 0.42017(19) 0.42017(19) 0.0000 0.0215(5) Uani 1 2 d S . . N2 N 1.05590(19) 1.05590(19) 0.0000 0.0219(5) Uani 1 2 d S . . C1 C 0.5839(2) 0.3812(2) 0.01085(12) 0.0272(5) Uani 1 1 d . . . H1A H 0.6121 0.2678 0.0189 0.033 Uiso 1 1 calc R . . C2 C 0.7138(3) 0.5005(3) 0.01080(12) 0.0277(5) Uani 1 1 d . . . H2A H 0.8264 0.4678 0.0178 0.033 Uiso 1 1 calc R . . C3 C 0.6710(2) 0.6710(2) 0.0000 0.0207(6) Uani 1 2 d S . . C4 C 0.8051(2) 0.8051(2) 0.0000 0.0230(6) Uani 1 2 d S . . C5 C 0.7882(3) 0.9503(3) 0.04225(12) 0.0262(5) Uani 1 1 d . . . H5A H 0.6919 0.9662 0.0708 0.031 Uiso 1 1 calc R . . C6 C 0.9165(3) 1.0708(3) 0.04132(11) 0.0249(4) Uani 1 1 d . . . H6A H 0.9056 1.1664 0.0707 0.030 Uiso 1 1 calc R . . O1 O 0.37397(19) 0.1110(2) 0.07207(8) 0.0318(4) Uani 1 1 d . . . O2 O 0.4173(2) -0.0839(2) 0.15710(9) 0.0333(4) Uani 1 1 d . . . C7 C 0.3302(3) -0.0038(3) 0.11448(11) 0.0312(5) Uani 1 1 d . . . H7A H 0.2153 -0.0324 0.1135 0.037 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 0.01670(13) 0.01670(13) 0.02845(19) 0.00596(10) -0.00596(10) -0.00598(15) N1 0.0174(7) 0.0174(7) 0.0297(13) 0.0024(8) -0.0024(8) -0.0056(9) N2 0.0184(7) 0.0184(7) 0.0290(13) 0.0046(8) -0.0046(8) -0.0039(8) C1 0.0208(10) 0.0144(9) 0.0464(14) 0.0060(9) -0.0014(9) 0.0000(7) C2 0.0146(9) 0.0220(10) 0.0464(14) 0.0033(10) -0.0010(9) -0.0012(8) C3 0.0183(8) 0.0183(8) 0.0255(14) -0.0005(9) 0.0005(9) -0.0044(10) C4 0.0184(8) 0.0184(8) 0.0323(16) 0.0054(9) -0.0054(9) -0.0063(10) C5 0.0194(10) 0.0253(11) 0.0338(12) -0.0033(9) 0.0036(9) -0.0036(8) C6 0.0240(11) 0.0193(11) 0.0315(11) -0.0028(9) 0.0008(9) -0.0047(8) O1 0.0233(8) 0.0305(9) 0.0416(9) 0.0171(8) -0.0090(7) -0.0068(7) O2 0.0283(9) 0.0361(9) 0.0354(8) 0.0144(7) -0.0037(7) 0.0045(7) C7 0.0220(12) 0.0386(14) 0.0330(13) 0.0100(11) -0.0018(9) -0.0033(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 Cu1 O1 1.9774(14) . ? Cu1 O1 1.9774(14) 5 ? Cu1 N2 2.015(2) 1_445 ? Cu1 N1 2.031(2) . ? Cu1 O2 2.5284(15) 7 ? Cu1 O2 2.5284(15) 4_554 ? N1 C1 1.337(2) . ? N1 C1 1.337(2) 5 ? N2 C6 1.340(2) 5 ? N2 C6 1.340(2) . ? N2 Cu1 2.015(2) 1_665 ? C1 C2 1.385(3) . ? C2 C3 1.395(2) . ? C3 C2 1.395(2) 5 ? C3 C4 1.490(4) . ? C4 C5 1.388(2) . ? C4 C5 1.388(2) 5 ? C5 C6 1.383(3) . ? O1 C7 1.243(2) . ? O2 C7 1.218(3) . ? O2 Cu1 2.5284(15) 3_545 ? 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 176.70(9) . 5 ? O1 Cu1 N2 91.65(5) . 1_445 ? O1 Cu1 N2 91.65(5) 5 1_445 ? O1 Cu1 N1 88.35(5) . . ? O1 Cu1 N1 88.35(5) 5 . ? N2 Cu1 N1 180.00(6) 1_445 . ? O1 Cu1 O2 94.70(7) . 7 ? O1 Cu1 O2 85.13(7) 5 7 ? N2 Cu1 O2 93.04(4) 1_445 7 ? N1 Cu1 O2 86.96(4) . 7 ? O1 Cu1 O2 85.13(7) . 4_554 ? O1 Cu1 O2 94.70(7) 5 4_554 ? N2 Cu1 O2 93.04(4) 1_445 4_554 ? N1 Cu1 O2 86.96(4) . 4_554 ? O2 Cu1 O2 173.91(8) 7 4_554 ? C1 N1 C1 117.6(2) . 5 ? C1 N1 Cu1 121.22(11) . . ? C1 N1 Cu1 121.22(11) 5 . ? C6 N2 C6 117.9(2) 5 . ? C6 N2 Cu1 121.05(12) 5 1_665 ? C6 N2 Cu1 121.05(12) . 1_665 ? N1 C1 C2 123.62(18) . . ? C1 C2 C3 118.14(19) . . ? C2 C3 C2 118.9(2) 5 . ? C2 C3 C4 120.55(12) 5 . ? C2 C3 C4 120.55(12) . . ? C5 C4 C5 118.3(3) . 5 ? C5 C4 C3 120.85(13) . . ? C5 C4 C3 120.85(13) 5 . ? C6 C5 C4 119.0(2) . . ? N2 C6 C5 122.86(19) . . ? C7 O1 Cu1 129.69(16) . . ? C7 O2 Cu1 117.15(15) . 3_545 ? O2 C7 O1 128.8(2) . . ? 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 Cu1 N1 C1 32.26(12) . . . . ? O1 Cu1 N1 C1 -147.74(12) 5 . . . ? N2 Cu1 N1 C1 169.89(11) 1_445 . . . ? O2 Cu1 N1 C1 127.05(12) 7 . . . ? O2 Cu1 N1 C1 -52.95(12) 4_554 . . . ? O1 Cu1 N1 C1 -147.74(12) . . . 5 ? O1 Cu1 N1 C1 32.26(12) 5 . . 5 ? N2 Cu1 N1 C1 -10.11(11) 1_445 . . 5 ? O2 Cu1 N1 C1 -52.95(12) 7 . . 5 ? O2 Cu1 N1 C1 127.05(12) 4_554 . . 5 ? C1 N1 C1 C2 -0.57(17) 5 . . . ? Cu1 N1 C1 C2 179.43(17) . . . . ? N1 C1 C2 C3 1.1(3) . . . . ? C1 C2 C3 C2 -0.51(15) . . . 5 ? C1 C2 C3 C4 179.49(15) . . . . ? C2 C3 C4 C5 50.49(15) 5 . . . ? C2 C3 C4 C5 -129.51(15) . . . . ? C2 C3 C4 C5 -129.51(15) 5 . . 5 ? C2 C3 C4 C5 50.49(15) . . . 5 ? C5 C4 C5 C6 -0.73(14) 5 . . . ? C3 C4 C5 C6 179.27(14) . . . . ? C6 N2 C6 C5 -0.79(15) 5 . . . ? Cu1 N2 C6 C5 179.21(15) 1_665 . . . ? C4 C5 C6 N2 1.6(3) . . . . ? O1 Cu1 O1 C7 160.9(2) 5 . . . ? N2 Cu1 O1 C7 -19.1(2) 1_445 . . . ? N1 Cu1 O1 C7 160.9(2) . . . . ? O2 Cu1 O1 C7 74.1(2) 7 . . . ? O2 Cu1 O1 C7 -112.0(2) 4_554 . . . ? Cu1 O2 C7 O1 167.8(2) 3_545 . . . ? Cu1 O1 C7 O2 177.59(19) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.221 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.064 #END #END data_neutrons _database_code_CSD 211672 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Cu(HCO2)2(N2C4H4) _chemical_formula_sum 'C6 Cu H6 N2 O4' _chemical_formula_weight 233.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 11.405(3) _cell_length_b 7.5100(1) _cell_length_c 8.435(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.78(2) _cell_angle_gamma 90.00 _cell_volume 721.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 20(2) _cell_measurement_reflns_used 560 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 1.20 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 27 _exptl_absorpt_coefficient_mu '1.135 + 0.661(\l)cm^-1^' _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.6587 _exptl_absorpt_correction_T_max 0.8320 _exptl_special_details ; ? ; _diffrn_ambient_temperature 20(2) _diffrn_radiation_wavelength '0.71 - 4.20' _diffrn_radiation_type neutrons _diffrn_radiation_source 'Pulsed spallation source at IPNS' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'SCD area detector system' _diffrn_measurement_method 'TOF Laue' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1535 _diffrn_reflns_av_R_equivalents 0.0792 _diffrn_reflns_av_sigmaI/netI 0.0903 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 35.59 _diffrn_reflns_theta_max 55.26 _reflns_number_total 1076 _reflns_number_gt 1016 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'IPNS data aquisition software' _computing_cell_refinement 'LATCON (Argonne Programs)' _computing_data_reduction 'ANVRED (Argonne Programs)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Burnett & Johnson 1996)' _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^)+(0.0670P)^2^+0.7532P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 13.6(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1076 _refine_ls_number_parameters 89 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1654 _refine_ls_wR_factor_gt 0.1639 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.002 _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 0.2500 0.2500 0.0000 0.0007(4) Uani 1 2 d S . . C1 C -0.0014(2) 0.1747(2) 0.0205(3) 0.0029(4) Uani 1 1 d . . . H1A H -0.0035(7) 0.3167(6) 0.0352(11) 0.0195(19) Uani 1 1 d . . . N1 N 0.10142(13) 0.09889(16) -0.00321(19) 0.0022(3) Uani 1 1 d U . . C2 C 0.10293(18) -0.0760(2) -0.0238(3) 0.0032(4) Uani 1 1 d . . . H2A H 0.1867(6) -0.1380(7) -0.0433(11) 0.0188(18) Uani 1 1 d . . . O2 O 0.3525(2) 0.0109(3) 0.1108(3) 0.0045(4) Uani 1 1 d U . . C3 C 0.3342(2) -0.0303(2) 0.2485(3) 0.0037(4) Uani 1 1 d . . . H3A H 0.3635(9) 0.0579(8) 0.3444(9) 0.0253(19) Uani 1 1 d . . . O1 O 0.2837(2) -0.1713(3) 0.2879(3) 0.0048(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0005(7) 0.0012(5) 0.0006(8) 0.0003(6) 0.0002(8) -0.0001(6) C1 0.0024(6) 0.0017(5) 0.0048(8) -0.0015(6) 0.0017(8) 0.0005(5) H1A 0.020(3) 0.0066(12) 0.031(4) -0.007(2) -0.001(4) 0.0008(17) N1 0.0016(5) 0.0017(3) 0.0034(4) -0.0003(4) 0.0016(5) -0.0003(3) C2 0.0009(6) 0.0027(5) 0.0063(8) -0.0011(6) 0.0013(8) -0.0002(5) H2A 0.0097(18) 0.0125(15) 0.035(4) -0.007(3) 0.005(3) 0.0067(17) O2 0.0049(6) 0.0048(5) 0.0039(6) 0.0019(6) 0.0015(7) -0.0009(6) C3 0.0048(7) 0.0039(5) 0.0024(7) 0.0005(6) -0.0004(8) -0.0012(6) H3A 0.040(4) 0.019(2) 0.017(2) -0.002(3) -0.003(3) -0.018(3) O1 0.0069(9) 0.0036(6) 0.0037(7) 0.0008(7) -0.0008(9) -0.0019(7) _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 1.940(3) 4 ? Cu1 O1 1.940(3) 6 ? Cu1 N1 2.0386(15) 7 ? Cu1 N1 2.0386(15) . ? Cu1 O2 2.314(2) . ? C1 H1A 1.075(5) . ? C1 N1 1.327(3) . ? C1 C2 1.377(3) 5 ? N1 C2 1.325(2) . ? C2 H2A 1.083(7) . ? C2 C1 1.377(3) 5 ? O2 C3 1.230(4) . ? C3 H3A 1.086(6) . ? C3 O1 1.257(3) . ? O1 Cu1 1.940(3) 4_545 ? 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 180.0(2) 4 6 ? O1 Cu1 N1 91.12(10) 4 7 ? O1 Cu1 N1 88.88(10) 6 7 ? O1 Cu1 N1 88.88(10) 4 . ? O1 Cu1 N1 91.12(10) 6 . ? N1 Cu1 N1 180.0 7 . ? O1 Cu1 O2 89.02(10) 4 . ? O1 Cu1 O2 90.98(10) 6 . ? N1 Cu1 O2 91.34(7) 7 . ? N1 Cu1 O2 88.66(7) . . ? H1A C1 N1 117.9(5) . . ? H1A C1 C2 120.5(5) . 5 ? N1 C1 C2 121.50(17) . 5 ? C2 N1 C1 117.52(17) . . ? C2 N1 Cu1 122.51(15) . . ? C1 N1 Cu1 119.94(11) . . ? H2A C2 N1 117.6(4) . . ? H2A C2 C1 121.4(4) . 5 ? N1 C2 C1 121.0(2) . 5 ? C3 O2 Cu1 118.1(2) . . ? H3A C3 O2 119.3(5) . . ? H3A C3 O1 116.4(5) . . ? O2 C3 O1 124.2(2) . . ? C3 O1 Cu1 127.89(17) . 4_545 ? _refine_diff_density_max 0.202 _refine_diff_density_min -0.266 _refine_diff_density_rms 0.055