Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal SOciety of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Catalina Ruiz-Perez' _publ_contact_author_address ; Departamento de Fisica Fundamental II Universidad de La Laguna Avda Astrofisico Francisco Sanchez La Laguna Tenerife 38204 SPAIN ; _publ_contact_author_email CARUIZ@ULL.ES _publ_section_title ; Crystal Engineering of 3D Coordination Polymers by Pillaring Ferromagnetic Copper(II)-Methylmalonate Layers ; loop_ _publ_author_name 'Catalina Ruiz-Perez' 'Miguel Julve' 'F. Lloret' 'Jorge Pasan' 'Joaquin Sanchiz' data_compound-1 _database_code_depnum_ccdc_archive 'CCDC 635165' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C4 H6 Cu O5' _chemical_formula_weight 197.61 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' Cu Cu 0.3201 1.2651 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pn21m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, y, -z' '-x, y+1/2, z+1/2' '-x, y+1/2, -z+1/2' _cell_length_a 6.203(3) _cell_length_b 6.7961(12) _cell_length_c 6.998(2) _cell_angle_alpha 90.000(17) _cell_angle_beta 90.00(3) _cell_angle_gamma 90.00(3) _cell_volume 295.01(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prisms _exptl_crystal_colour Blue _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.022 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 178 _exptl_absorpt_coefficient_mu 3.633 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1821 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 5.32 _diffrn_reflns_theta_max 27.49 _reflns_number_total 687 _reflns_number_gt 638 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _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^)+(0.0439P)^2^+0.2720P] 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 0.51(4) _refine_ls_number_reflns 687 _refine_ls_number_parameters 66 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0872 _refine_ls_wR_factor_gt 0.0862 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.089 _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 O1 O 0.9483(5) 0.3641(6) 0.1965(5) 0.0324(9) Uani 1 1 d . . . O1W O 0.8021(10) -0.0175(9) 0.0000 0.0339(12) Uani 1 2 d S . . O2 O 0.7320(5) 0.5993(5) 0.2975(5) 0.0290(8) Uani 1 1 d . . . C1 C 0.7844(7) 0.4714(7) 0.1772(7) 0.0240(9) Uani 1 1 d . . . C2 C 0.6408(11) 0.4456(10) 0.0000 0.0248(13) Uani 1 2 d S . . C3 C 0.4427(12) 0.5764(12) 0.0000 0.0303(16) Uani 1 2 d S . . H2 H 0.593(10) 0.299(14) 0.0000 0.03(2) Uiso 1 2 d S . . H3A H 0.472(9) 0.688(19) 0.0000 0.013(15) Uiso 1 2 d S . . H3B H 0.363(8) 0.556(8) 0.106(7) 0.019(12) Uiso 1 1 d . . . H1W H 1.195(12) 0.438(11) 0.413(9) 0.05(3) Uiso 1 1 d . . . Cu1 Cu 1.07493(10) 0.1964 0.0000 0.0233(2) Uani 1 2 d S . . 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 O1 0.042(2) 0.035(2) 0.0209(16) -0.0038(14) -0.0050(14) 0.0082(16) O1W 0.048(3) 0.026(3) 0.028(3) 0.000 0.000 -0.003(2) O2 0.0348(17) 0.0289(19) 0.0232(16) -0.0058(13) -0.0009(15) 0.0004(14) C1 0.031(2) 0.024(2) 0.017(2) 0.0001(18) 0.0047(18) -0.0060(19) C2 0.027(3) 0.025(3) 0.022(3) 0.000 0.000 -0.002(3) C3 0.030(4) 0.032(4) 0.029(4) 0.000 0.000 -0.004(3) Cu1 0.0322(4) 0.0192(3) 0.0184(3) 0.000 0.000 -0.0014(5) _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 O1 C1 1.258(6) . ? O1 Cu1 1.951(4) . ? O1W Cu1 2.231(6) . ? O2 C1 1.252(6) . ? O2 Cu1 1.970(3) 3_755 ? C1 C2 1.537(6) . ? C2 C3 1.517(11) . ? C2 C1 1.537(6) 2 ? Cu1 O1 1.951(4) 2 ? Cu1 O2 1.970(3) 4_745 ? Cu1 O2 1.970(3) 3_744 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 Cu1 126.1(3) . . ? C1 O2 Cu1 123.9(3) . 3_755 ? O2 C1 O1 122.7(4) . . ? O2 C1 C2 118.1(5) . . ? O1 C1 C2 119.2(5) . . ? C3 C2 C1 113.7(4) . . ? C3 C2 C1 113.7(4) . 2 ? C1 C2 C1 107.6(5) . 2 ? O1 Cu1 O1 89.6(2) . 2 ? O1 Cu1 O2 86.19(15) . 4_745 ? O1 Cu1 O2 161.39(14) 2 4_745 ? O1 Cu1 O2 161.39(14) . 3_744 ? O1 Cu1 O2 86.19(15) 2 3_744 ? O2 Cu1 O2 92.0(2) 4_745 3_744 ? O1 Cu1 O1W 94.31(16) . . ? O1 Cu1 O1W 94.31(16) 2 . ? O2 Cu1 O1W 104.06(15) 4_745 . ? O2 Cu1 O1W 104.06(15) 3_744 . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.489 _refine_diff_density_min -0.842 _refine_diff_density_rms 0.086 data_compound2 _database_code_depnum_ccdc_archive 'CCDC 635166' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 Cu N O4' _chemical_formula_weight 219.66 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' Cu Cu 0.3201 1.2651 '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' _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 6.2854(2) _cell_length_b 16.4373(6) _cell_length_c 7.0129(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.594(2) _cell_angle_gamma 90.00 _cell_volume 723.80(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prisms _exptl_crystal_colour Blue _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.016 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 2.986 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4780 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 4.08 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1590 _reflns_number_gt 1381 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _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 fullcycle _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0258P)^2^+1.3627P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1590 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0382 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0738 _refine_ls_wR_factor_gt 0.0704 _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 1.166 _refine_ls_shift/su_mean 0.208 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 0.18444(6) 0.31124(2) 0.96194(5) 0.01699(13) Uani 1 1 d . . . O3 O 0.0125(3) 0.36151(12) 0.7539(3) 0.0220(4) Uani 1 1 d . . . O1 O -0.0011(3) 0.35304(13) 1.1564(3) 0.0232(5) Uani 1 1 d . . . O4 O 0.3524(3) 0.25223(13) 1.1596(3) 0.0240(5) Uani 1 1 d . . . O2 O 0.3569(4) 0.25996(13) 0.7676(3) 0.0235(5) Uani 1 1 d . . . C1 C -0.0986(5) 0.31454(17) 1.2782(4) 0.0176(6) Uani 1 1 d . . . C3 C -0.0951(4) 0.32054(17) 0.6335(4) 0.0175(6) Uani 1 1 d . . . C5 C 0.3012(5) 0.49891(19) 1.0558(5) 0.0226(6) Uani 1 1 d . . . N1 N 0.3791(4) 0.42879(15) 0.9933(4) 0.0200(5) Uani 1 1 d . . . C6 C 0.5791(5) 0.4308(2) 0.9379(5) 0.0228(6) Uani 1 1 d . . . H5 H 0.845(6) 0.505(2) 0.901(5) 0.023(9) Uiso 1 1 d . . . H6 H 0.643(6) 0.384(2) 0.911(5) 0.020(8) Uiso 1 1 d . . . C2A C -0.1870(8) 0.3600(3) 1.4481(6) 0.0232(15) Uani 0.541(9) 1 d P . 1 H2A H -0.1047 0.4106 1.4460 0.10(4) Uiso 0.541(9) 1 calc PR . 1 C4A C -0.3873(8) 0.3891(3) 1.4464(6) 0.042(2) Uani 0.541(9) 1 d PR . 1 H41A H -0.4563 0.3794 1.3236 0.16(4) Uiso 0.541(9) 1 calc PR . 1 H42A H -0.3837 0.4466 1.4713 0.18(5) Uiso 0.541(9) 1 calc PR . 1 H43A H -0.4647 0.3622 1.5430 0.16(5) Uiso 0.541(9) 1 calc PR . 1 C2B C -0.1451(10) 0.3678(3) 1.4508(7) 0.0243(19) Uani 0.459(9) 1 d P . 2 H2B H -0.2998 0.3599 1.4466 0.13(4) Uiso 0.459(9) 1 calc PR . 2 C4B C -0.1467(10) 0.4481(3) 1.4397(7) 0.048(3) Uani 0.459(9) 1 d PR . 2 H41B H -0.1252 0.4644 1.3105 0.12(4) Uiso 0.459(9) 1 calc PR . 2 H42B H -0.0347 0.4699 1.5222 0.12(5) Uiso 0.459(9) 1 calc PR . 2 H43B H -0.2815 0.4683 1.4783 0.27(7) Uiso 0.459(9) 1 calc PR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01717(19) 0.01827(19) 0.0156(2) -0.00098(13) 0.00209(13) 0.00158(14) O3 0.0262(11) 0.0187(10) 0.0209(11) -0.0022(8) -0.0018(9) 0.0025(9) O1 0.0267(11) 0.0209(10) 0.0228(11) 0.0045(8) 0.0108(9) 0.0035(9) O4 0.0282(12) 0.0254(11) 0.0181(10) -0.0058(8) -0.0029(9) 0.0060(9) O2 0.0278(11) 0.0227(11) 0.0206(10) 0.0029(8) 0.0068(9) 0.0070(9) C1 0.0166(13) 0.0222(14) 0.0139(13) -0.0006(11) 0.0005(11) 0.0041(11) C3 0.0166(13) 0.0213(14) 0.0146(13) 0.0012(11) 0.0028(11) 0.0042(11) C5 0.0164(13) 0.0240(15) 0.0276(16) -0.0028(12) 0.0041(12) -0.0005(12) N1 0.0184(11) 0.0205(12) 0.0212(13) -0.0003(10) 0.0018(10) -0.0018(10) C6 0.0204(14) 0.0225(15) 0.0257(16) -0.0036(12) 0.0050(12) 0.0023(12) C2A 0.036(3) 0.017(3) 0.017(3) 0.000(2) 0.006(2) 0.006(2) C4A 0.046(4) 0.060(5) 0.020(3) -0.007(3) -0.003(3) 0.037(4) C2B 0.028(4) 0.032(4) 0.013(3) -0.003(3) 0.001(3) 0.005(3) C4B 0.104(9) 0.018(4) 0.022(4) 0.001(3) 0.012(5) 0.009(5) _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 1.958(2) . ? Cu1 O3 1.959(2) . ? Cu1 O4 1.961(2) . ? Cu1 O2 1.969(2) . ? Cu1 N1 2.292(3) . ? O3 C3 1.254(4) . ? O1 C1 1.246(4) . ? O4 C3 1.256(4) 4_666 ? O2 C1 1.258(4) 4_665 ? C1 O2 1.258(4) 4_566 ? C1 C2A 1.532(6) . ? C1 C2B 1.532(5) . ? C3 O4 1.256(4) 4_565 ? C3 C2B 1.519(5) 1_554 ? C3 C2A 1.542(6) 1_554 ? C5 N1 1.334(4) . ? C5 C6 1.379(5) 3_667 ? N1 C6 1.333(4) . ? C6 C5 1.379(5) 3_667 ? C2A C4A 1.3461 . ? C2A C3 1.542(6) 1_556 ? C2B C4B 1.3226 . ? C2B C3 1.519(5) 1_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O3 92.59(10) . . ? O1 Cu1 O4 89.98(10) . . ? O3 Cu1 O4 175.25(9) . . ? O1 Cu1 O2 174.87(10) . . ? O3 Cu1 O2 88.14(9) . . ? O4 Cu1 O2 88.96(9) . . ? O1 Cu1 N1 88.26(10) . . ? O3 Cu1 N1 89.43(10) . . ? O4 Cu1 N1 94.65(10) . . ? O2 Cu1 N1 96.83(10) . . ? C3 O3 Cu1 122.5(2) . . ? C1 O1 Cu1 128.8(2) . . ? C3 O4 Cu1 120.3(2) 4_666 . ? C1 O2 Cu1 120.3(2) 4_665 . ? O1 C1 O2 124.7(3) . 4_566 ? O1 C1 C2A 119.5(3) . . ? O2 C1 C2A 115.7(3) 4_566 . ? O1 C1 C2B 111.6(2) . . ? O2 C1 C2B 123.6(2) 4_566 . ? C2A C1 C2B 10.9(2) . . ? O3 C3 O4 123.4(3) . 4_565 ? O3 C3 C2B 112.2(2) . 1_554 ? O4 C3 C2B 124.4(3) 4_565 1_554 ? O3 C3 C2A 120.8(3) . 1_554 ? O4 C3 C2A 115.7(3) 4_565 1_554 ? C2B C3 C2A 10.9(3) 1_554 1_554 ? N1 C5 C6 121.8(3) . 3_667 ? C5 N1 C6 116.1(3) . . ? C5 N1 Cu1 123.9(2) . . ? C6 N1 Cu1 119.9(2) . . ? N1 C6 C5 122.1(3) . 3_667 ? C4A C2A C1 122.6(2) . . ? C4A C2A C3 118.1(2) . 1_556 ? C1 C2A C3 108.4(3) . 1_556 ? C4B C2B C3 124.1(2) . 1_556 ? C4B C2B C1 121.7(2) . . ? C3 C2B C1 109.6(3) 1_556 . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.411 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.088 # Attachment 'compound3.cif' data_compound-3 _database_code_depnum_ccdc_archive 'CCDC 635167' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H10 Cu N O5' _chemical_formula_weight 275.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 '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' _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 7.2395(4) _cell_length_b 19.4035(14) _cell_length_c 7.3889(3) _cell_angle_alpha 90.000(5) _cell_angle_beta 91.844(5) _cell_angle_gamma 90.000(5) _cell_volume 1037.39(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Sheets _exptl_crystal_colour Blue _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 2.110 _exptl_absorpt_correction_type sadabs _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'horizonally mounted graphite crystal' _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6209 _diffrn_reflns_av_R_equivalents 0.0475 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 6.45 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2297 _reflns_number_gt 1708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics CRYSTALMAKER _computing_publication_material 'PARST97 (Nardelli, 1997)' _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^)+(0.0185P)^2^+6.8543P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2297 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1145 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3031(10) 0.3222(3) 0.7342(7) 0.0322(15) Uani 1 1 d . . . C2 C 0.4745(11) 0.3644(3) 0.6900(9) 0.0366(17) Uani 1 1 d . . . C3 C 0.6469(10) 0.3220(3) 0.7374(7) 0.0307(15) Uani 1 1 d . . . C4 C 0.4786(17) 0.4350(4) 0.7756(11) 0.054(2) Uani 1 1 d . . . C5 C 0.531(2) 0.0739(4) 0.6374(12) 0.105(5) Uani 1 1 d . . . H5 H 0.5590 0.0658 0.5174 0.126 Uiso 1 1 calc R . . C6 C 0.538(2) 0.0188(4) 0.7542(11) 0.113(5) Uani 1 1 d . . . H4 H 0.5699 -0.0247 0.7127 0.136 Uiso 1 1 calc R . . C7 C 0.4979(7) 0.0286(3) 0.9331(7) 0.0177(11) Uani 1 1 d . . . C8 C 0.4667(10) 0.0951(3) 0.9830(9) 0.0341(15) Uani 1 1 d . . . H2 H 0.4496 0.1058 1.1040 0.041 Uiso 1 1 calc R . . C9 C 0.4606(9) 0.1465(3) 0.8544(7) 0.0277(14) Uani 1 1 d . . . H1 H 0.4362 0.1912 0.8925 0.033 Uiso 1 1 calc R . . Cu1 Cu 0.47499(7) 0.21292(3) 0.49562(8) 0.00899(17) Uani 1 1 d . . . N1 N 0.4868(6) 0.1364(2) 0.6822(5) 0.0141(9) Uani 1 1 d . . . O1 O 0.1989(6) 0.3431(2) 0.8556(5) 0.0353(11) Uani 1 1 d . . . O2 O 0.2714(6) 0.2670(2) 0.6451(5) 0.0327(11) Uani 1 1 d . . . O1W O 0.4765(8) 0.2843(2) 0.3041(5) 0.0203(8) Uani 1 1 d . . . O3 O 0.7581(6) 0.3443(2) 0.8572(5) 0.0329(10) Uani 1 1 d . . . O4 O 0.6719(6) 0.26651(19) 0.6510(5) 0.0306(10) Uani 1 1 d . . . H1W H 0.563(11) 0.276(4) 0.252(11) 0.05(3) Uiso 1 1 d . . . H2W H 0.398(10) 0.283(4) 0.259(10) 0.03(3) Uiso 1 1 d . . . H10 H 0.557(15) 0.467(6) 0.718(15) 0.11(4) Uiso 1 1 d . . . H11 H 0.365(9) 0.460(4) 0.735(9) 0.035(19) Uiso 1 1 d . . . H12 H 0.481(8) 0.432(3) 0.909(11) 0.037(19) Uiso 1 1 d . . . H13 H 0.470(10) 0.371(4) 0.577(11) 0.06(2) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.078(5) 0.011(3) 0.009(3) 0.004(2) 0.004(3) 0.003(3) C2 0.091(5) 0.009(3) 0.011(3) 0.000(2) 0.010(3) -0.001(3) C3 0.071(4) 0.011(3) 0.010(3) 0.003(2) 0.008(3) -0.013(3) C4 0.127(8) 0.011(3) 0.024(4) -0.002(3) 0.010(5) 0.003(4) C5 0.277(15) 0.016(4) 0.024(4) 0.009(3) 0.047(7) 0.028(6) C6 0.305(17) 0.017(4) 0.022(4) 0.009(3) 0.055(7) 0.032(6) C7 0.035(3) 0.012(2) 0.006(2) 0.004(2) 0.001(2) -0.001(2) C8 0.073(4) 0.017(3) 0.014(3) 0.000(3) 0.012(3) 0.010(3) C9 0.060(4) 0.015(3) 0.009(3) 0.002(2) 0.008(3) 0.014(3) Cu1 0.0142(3) 0.0073(3) 0.0055(3) 0.0013(3) 0.00018(18) -0.0004(3) N1 0.024(2) 0.011(2) 0.007(2) 0.0017(17) 0.0008(17) -0.0002(17) O1 0.070(3) 0.023(2) 0.013(2) -0.0030(17) 0.001(2) 0.005(2) O2 0.071(3) 0.015(2) 0.012(2) -0.0018(16) 0.0094(19) -0.0058(19) O1W 0.038(3) 0.0138(19) 0.0093(19) 0.0001(17) 0.0013(19) 0.003(2) O3 0.063(3) 0.020(2) 0.016(2) -0.0079(17) 0.0122(19) -0.018(2) O4 0.070(3) 0.0101(19) 0.011(2) -0.0026(15) -0.0071(19) -0.0003(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.258(7) . ? C1 O2 1.274(7) . ? C1 C2 1.530(10) . ? C2 C4 1.509(9) . ? C2 C3 1.526(10) . ? C3 O3 1.254(7) . ? C3 O4 1.268(7) . ? C5 N1 1.301(9) . ? C5 C6 1.373(10) . ? C6 C7 1.376(9) . ? C7 C8 1.362(7) . ? C7 C7 1.487(10) 3_657 ? C8 C9 1.378(8) . ? C9 N1 1.307(6) . ? Cu1 O1W 1.980(4) . ? Cu1 N1 2.025(4) . ? Cu1 O4 2.080(4) . ? Cu1 O2 2.144(4) . ? Cu1 O3 2.154(5) 4_565 ? Cu1 O1 2.234(5) 4_665 ? O1 Cu1 2.234(5) 4_566 ? O3 Cu1 2.154(5) 4_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 122.5(6) . . ? O1 C1 C2 119.2(5) . . ? O2 C1 C2 118.2(5) . . ? C4 C2 C3 112.8(7) . . ? C4 C2 C1 113.7(7) . . ? C3 C2 C1 109.0(5) . . ? O3 C3 O4 123.3(6) . . ? O3 C3 C2 118.5(5) . . ? O4 C3 C2 118.1(5) . . ? N1 C5 C6 124.9(7) . . ? C5 C6 C7 119.4(7) . . ? C8 C7 C6 115.7(5) . . ? C8 C7 C7 121.8(6) . 3_657 ? C6 C7 C7 122.3(6) . 3_657 ? C7 C8 C9 120.1(5) . . ? N1 C9 C8 124.1(5) . . ? O1W Cu1 N1 176.10(19) . . ? O1W Cu1 O4 91.44(18) . . ? N1 Cu1 O4 88.71(16) . . ? O1W Cu1 O2 92.59(18) . . ? N1 Cu1 O2 91.31(16) . . ? O4 Cu1 O2 86.64(17) . . ? O1W Cu1 O3 92.41(18) . 4_565 ? N1 Cu1 O3 87.69(16) . 4_565 ? O4 Cu1 O3 174.78(16) . 4_565 ? O2 Cu1 O3 89.67(16) . 4_565 ? O1W Cu1 O1 89.36(18) . 4_665 ? N1 Cu1 O1 86.74(16) . 4_665 ? O4 Cu1 O1 90.23(16) . 4_665 ? O2 Cu1 O1 176.35(16) . 4_665 ? O3 Cu1 O1 93.33(15) 4_565 4_665 ? C5 N1 C9 115.6(5) . . ? C5 N1 Cu1 121.1(4) . . ? C9 N1 Cu1 123.3(4) . . ? C1 O1 Cu1 129.3(4) . 4_566 ? C1 O2 Cu1 124.2(4) . . ? C3 O3 Cu1 126.8(4) . 4_666 ? C3 O4 Cu1 126.6(4) . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 1.013 _refine_diff_density_min -0.901 _refine_diff_density_rms 0.137