Electronic Supplementary Material for CrystEngComm This Journal is (c) The Royal Society of Chemistry 2006 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 ; Versatile supramolecular self-assembly. Part II. Network formation and magnetic behaviour of copper(II) malonate anions in ammonium derivatives. ; loop_ _publ_author_name 'Catalina Ruiz-Perez' 'Fernando S. Delgado' 'Miguel Julve' 'F. Lloret' 'Joaquin Shanchiz' # Attachment 'compound1a.cif' data_compound1a _database_code_depnum_ccdc_archive 'CCDC 253062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H12 Cu N2 O8' _chemical_formula_weight 303.72 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 orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2 d' _symmetry_Int_Tables_number 43 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+3/4, -y+5/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+5/4, -y+3/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+5/4, -y+5/4, z+1/4' _cell_length_a 13.8481(3) _cell_length_b 16.4536(2) _cell_length_c 9.1071(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2075.06(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular prism' _exptl_crystal_colour 'palid blue' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.944 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 2.142 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS, Sheldrick, 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 '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 3607 _diffrn_reflns_av_R_equivalents 0.0225 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 6.76 _diffrn_reflns_theta_max 29.98 _reflns_number_total 1264 _reflns_number_gt 1171 _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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0272P)^2^+0.7267P] 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 0.542(16) _refine_ls_number_reflns 1264 _refine_ls_number_parameters 103 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0244 _refine_ls_R_factor_gt 0.0197 _refine_ls_wR_factor_ref 0.0491 _refine_ls_wR_factor_gt 0.0479 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.072 _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 0.43900(5) 0.01724(9) Uani 1 2 d S . . O1 O 0.21229(13) -0.17406(9) 0.28414(17) 0.0227(3) Uani 1 1 d . . . O2 O 0.21208(14) -0.17562(9) 0.59373(16) 0.0237(3) Uani 1 1 d . . . O3 O 0.13782(11) -0.06466(8) 0.20482(19) 0.0236(3) Uani 1 1 d . . . O4 O 0.16466(10) -0.05947(7) 0.6896(2) 0.0246(3) Uani 1 1 d . . . C1 C 0.18471(14) -0.10152(12) 0.3016(2) 0.0159(4) Uani 1 1 d . . . C2 C 0.21193(14) -0.05594(10) 0.4395(3) 0.0188(3) Uani 1 1 d . . . C3 C 0.19461(14) -0.09998(13) 0.5827(2) 0.0158(4) Uani 1 1 d . . . N11 N 0.18009(13) -0.15173(10) -0.0560(3) 0.0231(3) Uani 1 1 d . . . H11 H 0.163(2) -0.127(2) 0.018(4) 0.027(8) Uiso 1 1 d . . . H12 H 0.1480(16) -0.1994(14) -0.066(4) 0.025(5) Uiso 1 1 d . . . H13 H 0.167(4) -0.125(3) -0.129(6) 0.064(13) Uiso 1 1 d . . . H14 H 0.2424(18) -0.1609(13) -0.032(3) 0.020(6) Uiso 1 1 d . . . H1 H 0.1911(17) -0.0054(12) 0.444(3) 0.024(6) Uiso 1 1 d . . . H2 H 0.2774(18) -0.0472(12) 0.428(5) 0.023(6) 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 Cu1 0.02803(15) 0.01257(12) 0.01112(13) 0.000 0.000 0.00352(12) O1 0.0362(10) 0.0155(7) 0.0163(8) -0.0004(6) -0.0044(7) 0.0050(6) O2 0.0401(10) 0.0174(7) 0.0138(7) 0.0009(6) 0.0039(7) 0.0050(7) O3 0.0301(7) 0.0239(6) 0.0169(9) 0.0015(8) -0.0042(7) 0.0087(5) O4 0.0373(7) 0.0220(6) 0.0143(6) -0.0029(8) 0.0023(8) 0.0080(5) C1 0.0180(9) 0.0164(8) 0.0133(10) 0.0010(8) 0.0016(7) -0.0011(7) C2 0.0271(8) 0.0141(7) 0.0150(8) -0.0022(9) 0.0016(10) 0.0003(6) C3 0.0155(9) 0.0194(9) 0.0126(9) -0.0009(7) -0.0005(7) 0.0003(7) N11 0.0283(8) 0.0229(7) 0.0180(8) 0.0020(10) 0.0007(10) -0.0011(6) _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 1.9389(15) . ? Cu1 O2 1.9389(15) 14_545 ? Cu1 O1 1.9553(16) 14_545 ? Cu1 O1 1.9553(16) . ? O1 C1 1.263(2) . ? O2 C3 1.272(2) . ? O3 C1 1.251(3) . ? O4 C3 1.250(3) . ? C1 C2 1.511(3) . ? C2 C3 1.511(3) . ? 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 86.77(9) . 14_545 ? O2 Cu1 O1 179.41(8) . 14_545 ? O2 Cu1 O1 92.78(5) 14_545 14_545 ? O2 Cu1 O1 92.78(5) . . ? O2 Cu1 O1 179.41(8) 14_545 . ? O1 Cu1 O1 87.68(9) 14_545 . ? C1 O1 Cu1 126.44(14) . . ? C3 O2 Cu1 127.72(14) . . ? O3 C1 O1 121.77(19) . . ? O3 C1 C2 118.32(18) . . ? O1 C1 C2 119.86(18) . . ? C3 C2 C1 116.11(14) . . ? O4 C3 O2 121.6(2) . . ? O4 C3 C2 117.95(19) . . ? O2 C3 C2 120.48(18) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.247 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.051 # Attachment 'compound2.cif' data_compound2 _database_code_depnum_ccdc_archive 'CCDC 253063' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H16 Cu N2 O8' _chemical_formula_weight 331.77 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.6866(2) _cell_length_b 9.0585(3) _cell_length_c 8.9681(3) _cell_angle_alpha 90.00 _cell_angle_beta 115.198(2) _cell_angle_gamma 90.00 _cell_volume 638.53(3) _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 sheet _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.726 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 342 _exptl_absorpt_coefficient_mu 1.748 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS, Sheldrick, 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 '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 3684 _diffrn_reflns_av_R_equivalents 0.0154 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 6.42 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1449 _reflns_number_gt 1255 _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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0351P)^2^+0.1243P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1449 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0228 _refine_ls_wR_factor_ref 0.0620 _refine_ls_wR_factor_gt 0.0594 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 0.0000 0.5000 0.0000 0.02424(11) Uani 1 2 d S . . O1 O -0.07152(14) 0.31937(13) -0.12325(15) 0.0311(3) Uani 1 1 d . . . O2 O 0.24065(13) 0.44597(14) 0.08020(12) 0.0249(2) Uani 1 1 d . . . O3 O -0.04455(17) 0.13676(15) -0.27147(17) 0.0411(3) Uani 1 1 d . . . O4 O 0.44600(15) 0.31529(16) 0.06217(14) 0.0381(3) Uani 1 1 d . . . C1 C 0.01102(19) 0.24961(17) -0.18955(19) 0.0230(3) Uani 1 1 d . . . C2 C 0.1795(2) 0.31266(19) -0.17045(18) 0.0239(3) Uani 1 1 d . . . C3 C 0.29643(18) 0.36156(16) 0.00228(17) 0.0218(3) Uani 1 1 d . . . N11 N 0.6364(2) 0.29344(19) 0.3983(2) 0.0322(3) Uani 1 1 d . . . C11 C 0.6973(4) 0.4391(3) 0.4691(3) 0.0502(5) Uani 1 1 d . . . H1 H 0.233(3) 0.242(2) -0.210(2) 0.031(5) Uiso 1 1 d . . . H2 H 0.156(3) 0.398(2) -0.232(2) 0.033(5) Uiso 1 1 d . . . H11 H 0.568(3) 0.300(3) 0.289(3) 0.046(6) Uiso 1 1 d . . . H12 H 0.583(3) 0.245(3) 0.447(3) 0.048(6) Uiso 1 1 d . . . H13 H 0.715(3) 0.243(3) 0.411(3) 0.043(6) Uiso 1 1 d . . . H14 H 0.624(5) 0.499(3) 0.423(5) 0.077(11) Uiso 1 1 d . . . H15 H 0.739(4) 0.443(3) 0.592(4) 0.064(7) Uiso 1 1 d . . . H16 H 0.793(6) 0.469(4) 0.444(4) 0.090(11) 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 Cu1 0.01684(14) 0.02190(16) 0.03468(17) -0.01057(10) 0.01165(11) -0.00196(10) O1 0.0248(6) 0.0275(6) 0.0466(6) -0.0158(5) 0.0206(5) -0.0077(5) O2 0.0190(5) 0.0296(6) 0.0263(5) -0.0064(4) 0.0098(4) 0.0006(5) O3 0.0438(7) 0.0323(7) 0.0537(7) -0.0232(6) 0.0270(6) -0.0130(6) O4 0.0228(6) 0.0547(8) 0.0336(6) -0.0052(6) 0.0089(5) 0.0127(6) C1 0.0242(7) 0.0202(8) 0.0234(6) -0.0017(5) 0.0091(5) 0.0007(6) C2 0.0250(7) 0.0260(8) 0.0234(7) -0.0028(6) 0.0129(6) 0.0012(6) C3 0.0196(7) 0.0223(7) 0.0248(7) 0.0017(5) 0.0108(6) 0.0005(6) N11 0.0238(7) 0.0392(9) 0.0347(8) 0.0014(6) 0.0134(6) 0.0045(7) C11 0.0578(14) 0.0411(12) 0.0543(13) -0.0006(10) 0.0265(11) -0.0041(12) _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 1.9236(11) . ? Cu1 O1 1.9236(11) 3_565 ? Cu1 O2 1.9613(10) . ? Cu1 O2 1.9613(10) 3_565 ? Cu1 O3 2.5620(15) 4_566 ? Cu1 O3 2.5620(15) 2_554 ? O1 C1 1.2767(19) . ? O2 C3 1.2633(18) . ? O3 C1 1.2312(19) . ? O4 C3 1.2483(18) . ? C1 C2 1.511(2) . ? C2 C3 1.513(2) . ? N11 C11 1.463(3) . ? 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 . 3_565 ? O1 Cu1 O2 91.81(5) . . ? O1 Cu1 O2 88.19(5) 3_565 . ? O1 Cu1 O2 88.19(5) . 3_565 ? O1 Cu1 O2 91.81(5) 3_565 3_565 ? O2 Cu1 O2 180.0 . 3_565 ? O3 Cu1 O1 85.77(4) 4_566 . ? O3 Cu1 O2 94.96(5) 4_566 . ? O3 Cu1 O1 94.23(4) 4_566 3_565 ? O3 Cu1 O2 85.04(5) 4_566 3_565 ? O3 Cu1 O1 94.23(4) 2_554 . ? O3 Cu1 O2 85.04(5) 2_554 . ? O3 Cu1 O1 85.77(4) 2_554 3_565 ? O3 Cu1 O2 94.96(5) 2_554 3_565 ? O3 Cu1 O3 180.0 4_566 2_554 ? C1 O1 Cu1 125.49(10) . . ? C3 O2 Cu1 123.24(9) . . ? O3 C1 O1 122.25(15) . . ? O3 C1 C2 119.74(14) . . ? O1 C1 C2 117.96(13) . . ? C1 C2 C3 114.99(12) . . ? O4 C3 O2 122.64(13) . . ? O4 C3 C2 117.67(14) . . ? O2 C3 C2 119.69(13) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.244 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.063 # Attachment 'compound3.cif' data_compound3 _database_code_depnum_ccdc_archive 'CCDC 253064' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H20 Cu N2 O11' _chemical_formula_weight 383.80 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 11.670(2) _cell_length_b 8.408(2) _cell_length_c 15.323(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.38(3) _cell_angle_gamma 90.00 _cell_volume 1500.9(5) _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 prism _exptl_crystal_colour blue _exptl_crystal_size_max 1 _exptl_crystal_size_mid 0.8 _exptl_crystal_size_min 0.6 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 796 _exptl_absorpt_coefficient_mu 1.514 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS, Sheldrick, 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 '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 10895 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 6.47 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3321 _reflns_number_gt 2815 _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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0577P)^2^+1.1076P] 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 0.114(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3321 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.1018 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 Cu1 Cu 0.25451(2) 0.19386(3) 0.753927(17) 0.02224(15) Uani 1 1 d . . . O1 O 0.20186(14) 0.39955(19) 0.78941(11) 0.0272(4) Uani 1 1 d . . . O2 O 0.14322(14) 0.08290(19) 0.82063(11) 0.0270(4) Uani 1 1 d . . . O3 O 0.08034(16) 0.5695(2) 0.83999(13) 0.0350(4) Uani 1 1 d . . . O4 O -0.02074(16) 0.0516(2) 0.88180(13) 0.0339(4) Uani 1 1 d . . . C1 C 0.1065(2) 0.4327(3) 0.81928(14) 0.0219(5) Uani 1 1 d . . . C2 C 0.0147(2) 0.3066(3) 0.8259(2) 0.0372(7) Uani 1 1 d . . . C3 C 0.0482(2) 0.1362(3) 0.84505(14) 0.0225(5) Uani 1 1 d . . . O11 O 0.36491(14) 0.30616(18) 0.68738(11) 0.0238(4) Uani 1 1 d . . . O12 O 0.29671(14) -0.01019(19) 0.70904(11) 0.0280(4) Uani 1 1 d . . . O13 O 0.52607(15) 0.3363(2) 0.62181(13) 0.0298(4) Uani 1 1 d . . . O14 O 0.41059(16) -0.1820(2) 0.65208(14) 0.0341(4) Uani 1 1 d . . . C11 C 0.45633(19) 0.2506(3) 0.65753(14) 0.0205(4) Uani 1 1 d . . . C12 C 0.4848(2) 0.0762(3) 0.6683(2) 0.0295(5) Uani 1 1 d . . . C13 C 0.3899(2) -0.0449(3) 0.67623(14) 0.0224(5) Uani 1 1 d . . . N21 N 0.25934(19) 0.5794(3) 0.62073(13) 0.0237(4) Uani 1 1 d . . . N22 N 0.23806(19) 0.7047(3) 0.38584(13) 0.0244(4) Uani 1 1 d . . . C21 C 0.2746(2) 0.5672(3) 0.52600(15) 0.0269(5) Uani 1 1 d . . . C22 C 0.2193(3) 0.7085(3) 0.48036(16) 0.0276(5) Uani 1 1 d . . . O1W O 0.39391(16) 0.1617(2) 0.87792(12) 0.0333(4) Uani 1 1 d . . . O2W O 0.1074(2) 0.2328(3) 0.60791(19) 0.0571(6) Uani 1 1 d . . . O3W O 0.2873(3) 0.1047(3) 0.50084(17) 0.0706(8) Uani 1 1 d . . . H1 H -0.042(3) 0.343(5) 0.868(2) 0.051(10) Uiso 1 1 d . . . H2 H -0.037(4) 0.301(5) 0.765(3) 0.077(13) Uiso 1 1 d . . . H11 H 0.532(3) 0.048(4) 0.623(2) 0.038(8) Uiso 1 1 d . . . H12 H 0.535(3) 0.067(5) 0.722(3) 0.064(11) Uiso 1 1 d . . . H21 H 0.294(3) 0.665(4) 0.642(2) 0.028(7) Uiso 1 1 d . . . H22 H 0.184(3) 0.582(3) 0.6287(19) 0.028(7) Uiso 1 1 d . . . H23 H 0.294(3) 0.494(4) 0.6507(19) 0.029(7) Uiso 1 1 d . . . H24 H 0.245(3) 0.464(3) 0.5063(18) 0.026(7) Uiso 1 1 d . . . H25 H 0.352(3) 0.567(4) 0.523(2) 0.036(8) Uiso 1 1 d . . . H26 H 0.253(3) 0.808(4) 0.502(2) 0.051(10) Uiso 1 1 d . . . H27 H 0.147(3) 0.701(3) 0.484(2) 0.034(8) Uiso 1 1 d . . . H28 H 0.203(3) 0.610(4) 0.358(2) 0.043(9) Uiso 1 1 d . . . H29 H 0.316(3) 0.706(4) 0.378(2) 0.042(9) Uiso 1 1 d . . . H30 H 0.203(3) 0.791(4) 0.359(2) 0.033(8) 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 Cu1 0.0227(2) 0.0157(2) 0.0296(2) 0.00154(10) 0.01245(12) 0.00024(10) O1 0.0264(9) 0.0201(8) 0.0363(9) -0.0019(7) 0.0124(7) -0.0013(7) O2 0.0221(8) 0.0206(8) 0.0398(9) 0.0067(7) 0.0139(7) 0.0032(6) O3 0.0299(10) 0.0212(9) 0.0539(11) -0.0123(8) 0.0043(8) 0.0017(7) O4 0.0272(10) 0.0306(10) 0.0457(10) 0.0071(8) 0.0165(8) -0.0021(7) C1 0.0220(11) 0.0203(11) 0.0232(10) -0.0014(8) 0.0010(8) 0.0017(8) C2 0.0213(13) 0.0214(14) 0.070(2) 0.0034(12) 0.0145(13) 0.0023(9) C3 0.0206(11) 0.0214(12) 0.0258(11) -0.0005(9) 0.0045(8) -0.0006(9) O11 0.0219(8) 0.0188(8) 0.0320(8) 0.0045(6) 0.0111(7) 0.0018(6) O12 0.0256(9) 0.0185(8) 0.0412(9) -0.0031(7) 0.0119(7) -0.0005(7) O13 0.0244(9) 0.0256(9) 0.0411(10) 0.0042(7) 0.0147(7) -0.0025(7) O14 0.0282(10) 0.0197(9) 0.0549(11) -0.0109(7) 0.0063(8) 0.0011(7) C11 0.0205(11) 0.0204(11) 0.0208(10) -0.0006(8) 0.0015(8) -0.0003(8) C12 0.0195(12) 0.0223(12) 0.0474(15) -0.0006(11) 0.0089(11) 0.0014(9) C13 0.0216(12) 0.0209(11) 0.0246(10) -0.0002(8) 0.0004(8) 0.0011(8) N21 0.0234(11) 0.0234(11) 0.0246(9) 0.0032(8) 0.0034(8) -0.0004(9) N22 0.0257(11) 0.0232(11) 0.0244(10) 0.0029(8) 0.0029(8) 0.0018(8) C21 0.0314(14) 0.0246(13) 0.0250(11) 0.0001(9) 0.0049(9) 0.0057(10) C22 0.0311(15) 0.0265(13) 0.0256(12) 0.0005(9) 0.0046(10) 0.0066(10) O1W 0.0253(10) 0.0363(10) 0.0387(10) 0.0049(8) 0.0067(8) -0.0028(8) O2W 0.0365(13) 0.0430(13) 0.0941(19) -0.0022(12) 0.0231(12) -0.0045(10) O3W 0.103(2) 0.0526(15) 0.0589(15) 0.0037(12) 0.0250(15) 0.0032(14) _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 O12 1.9233(17) . ? Cu1 O1 1.9245(17) . ? Cu1 O11 1.9355(16) . ? Cu1 O2 1.9386(17) . ? Cu1 O1W 2.442(2) . ? Cu1 O2W 2.758(3) . ? O1 C1 1.259(3) . ? O2 C3 1.272(3) . ? O3 C1 1.236(3) . ? O4 C3 1.234(3) . ? C1 C2 1.514(3) . ? C2 C3 1.510(3) . ? C2 H1 1.00(4) . ? C2 H2 1.09(5) . ? O11 C11 1.274(3) . ? O12 C13 1.259(3) . ? O13 C11 1.239(3) . ? O14 C13 1.239(3) . ? C11 C12 1.510(3) . ? C12 C13 1.514(3) . ? C12 H11 0.94(4) . ? C12 H12 0.99(4) . ? N21 C21 1.477(3) . ? N21 H21 0.88(3) . ? N21 H22 0.89(3) . ? N21 H23 0.94(3) . ? N22 C22 1.478(3) . ? N22 H28 0.98(4) . ? N22 H29 0.93(4) . ? N22 H30 0.92(3) . ? C21 C22 1.505(3) . ? C21 H24 0.98(3) . ? C21 H25 0.90(3) . ? C22 H26 0.98(4) . ? C22 H27 0.85(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 O12 Cu1 O1 174.52(7) . . ? O12 Cu1 O11 93.11(7) . . ? O1 Cu1 O11 86.79(7) . . ? O12 Cu1 O2 87.30(7) . . ? O1 Cu1 O2 92.78(7) . . ? O11 Cu1 O2 179.55(6) . . ? O1W Cu1 O1 95.10(7) . . ? O1W Cu1 O2 88.44(7) . . ? O1W Cu1 O11 91.74(7) . . ? O1W Cu1 O12 90.37(7) . . ? O2W Cu1 O1 85.91(7) . . ? O2W Cu1 O2 94.63(7) . . ? O2W Cu1 O11 85.20(7) . . ? O2W Cu1 O12 88.62(7) . . ? O1W Cu1 O2W 176.72(7) . . ? C1 O1 Cu1 127.25(15) . . ? C3 O2 Cu1 127.46(15) . . ? O3 C1 O1 122.4(2) . . ? O3 C1 C2 116.6(2) . . ? O1 C1 C2 120.9(2) . . ? C3 C2 C1 120.1(2) . . ? C3 C2 H1 110(2) . . ? C1 C2 H1 109(2) . . ? C3 C2 H2 104(2) . . ? C1 C2 H2 109(2) . . ? H1 C2 H2 103(3) . . ? O4 C3 O2 122.3(2) . . ? O4 C3 C2 117.8(2) . . ? O2 C3 C2 119.8(2) . . ? C11 O11 Cu1 127.42(15) . . ? C13 O12 Cu1 126.49(15) . . ? O13 C11 O11 122.1(2) . . ? O13 C11 C12 117.9(2) . . ? O11 C11 C12 120.0(2) . . ? C11 C12 C13 120.3(2) . . ? C11 C12 H11 107(2) . . ? C13 C12 H11 111(2) . . ? C11 C12 H12 107(2) . . ? C13 C12 H12 106(2) . . ? H11 C12 H12 105(3) . . ? O14 C13 O12 121.5(2) . . ? O14 C13 C12 116.5(2) . . ? O12 C13 C12 122.0(2) . . ? C21 N21 H21 110(2) . . ? C21 N21 H22 108.2(19) . . ? H21 N21 H22 111(3) . . ? C21 N21 H23 110.8(18) . . ? H21 N21 H23 106(3) . . ? H22 N21 H23 111(3) . . ? C22 N22 H28 111(2) . . ? C22 N22 H29 109(2) . . ? H28 N22 H29 110(3) . . ? C22 N22 H30 109(2) . . ? H28 N22 H30 107(3) . . ? H29 N22 H30 110(3) . . ? N21 C21 C22 109.2(2) . . ? N21 C21 H24 107.6(16) . . ? C22 C21 H24 114.9(16) . . ? N21 C21 H25 103(2) . . ? C22 C21 H25 112(2) . . ? H24 C21 H25 109(3) . . ? N22 C22 C21 110.7(2) . . ? N22 C22 H26 106(2) . . ? C21 C22 H26 111(2) . . ? N22 C22 H27 106(2) . . ? C21 C22 H27 108(2) . . ? H26 C22 H27 115(3) . . ? _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.964 _refine_diff_density_max 0.659 _refine_diff_density_min -0.978 _refine_diff_density_rms 0.120 # Attachment 'compound4.cif' data_compound4 _database_code_depnum_ccdc_archive 'CCDC 253065' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H16 Cu N2 O8' _chemical_formula_weight 343.78 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 orthorhombic _symmetry_space_group_name_H-M 'P b c n' _symmetry_space_group_name_Hall '-P 2n 2ab' _symmetry_Int_Tables_number 60 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 8.2680(4) _cell_length_b 16.9351(9) _cell_length_c 9.4736(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 90.000(4) _cell_angle_gamma 90.000(4) _cell_volume 1326.49(12) _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 'rectangular sheet' _exptl_crystal_colour 'dark blue' _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 708 _exptl_absorpt_coefficient_mu 1.686 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS, Sheldrick, Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type Mok\a _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 5634 _diffrn_reflns_av_R_equivalents 0.0218 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 5.10 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1425 _reflns_number_gt 1144 _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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0288P)^2^+2.5515P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1425 _refine_ls_number_parameters 124 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0581 _refine_ls_R_factor_gt 0.0426 _refine_ls_wR_factor_ref 0.0960 _refine_ls_wR_factor_gt 0.0905 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 0.0000 0.20442(3) 0.2500 0.0459(2) Uani 1 2 d S . . O1 O 0.1055(4) 0.28570(13) 0.3570(3) 0.0623(9) Uani 1 1 d . . . O2 O 0.0753(3) 0.12403(11) 0.3753(2) 0.0319(5) Uani 1 1 d . . . O3 O 0.2116(4) 0.33796(15) 0.5461(2) 0.0534(7) Uani 1 1 d . . . O4 O 0.1244(3) 0.07427(13) 0.5834(2) 0.0399(6) Uani 1 1 d . . . C1 C 0.1399(4) 0.28357(18) 0.4867(3) 0.0349(7) Uani 1 1 d . . . C2 C 0.0900(5) 0.2135(2) 0.5744(3) 0.0376(8) Uani 1 1 d . . . C3 C 0.0992(3) 0.13216(17) 0.5067(3) 0.0254(6) Uani 1 1 d . . . N11 N 0.2724(4) 0.46552(17) 0.3544(3) 0.0296(6) Uani 1 1 d . . . C11 C 0.1323(4) 0.51427(18) 0.3111(4) 0.0308(7) Uani 1 1 d . . . C12 C 0.0000 0.4638(2) 0.2500 0.0298(9) Uani 1 2 d S . . H1 H 0.163(5) 0.209(2) 0.662(5) 0.069(13) Uiso 1 1 d . . . H2 H -0.034(5) 0.225(2) 0.604(5) 0.065(13) Uiso 1 1 d . . . H11 H 0.251(5) 0.427(2) 0.412(4) 0.049(11) Uiso 1 1 d . . . H12 H 0.337(5) 0.495(3) 0.388(4) 0.050(12) Uiso 1 1 d . . . H13 H 0.319(5) 0.445(2) 0.283(4) 0.039(10) Uiso 1 1 d . . . H14 H 0.100(4) 0.5405(19) 0.391(4) 0.036(9) Uiso 1 1 d . . . H15 H 0.166(4) 0.552(2) 0.248(4) 0.039(9) Uiso 1 1 d . . . H16 H 0.045(4) 0.432(2) 0.177(4) 0.047(10) 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 Cu1 0.0788(5) 0.0193(3) 0.0396(4) 0.000 -0.0355(3) 0.000 O1 0.120(3) 0.0278(12) 0.0388(14) 0.0062(11) -0.0363(15) -0.0220(14) O2 0.0455(14) 0.0258(10) 0.0246(11) 0.0002(8) -0.0079(9) 0.0071(9) O3 0.076(2) 0.0481(14) 0.0362(13) -0.0106(11) -0.0019(13) -0.0332(13) O4 0.0503(16) 0.0387(12) 0.0306(12) 0.0120(10) -0.0038(10) 0.0018(11) C1 0.043(2) 0.0320(16) 0.0301(16) -0.0058(13) -0.0023(14) -0.0056(14) C2 0.047(2) 0.0383(17) 0.0272(17) -0.0042(14) 0.0041(15) -0.0091(16) C3 0.0188(15) 0.0306(14) 0.0268(15) 0.0034(12) 0.0004(12) -0.0013(11) N11 0.0268(16) 0.0303(14) 0.0316(14) -0.0069(13) -0.0030(12) -0.0015(12) C11 0.0280(18) 0.0280(15) 0.0365(17) -0.0050(14) -0.0053(14) 0.0016(12) C12 0.028(2) 0.0267(19) 0.035(2) 0.000 -0.001(2) 0.000 _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 1.9102(19) 4 ? Cu1 O2 1.9102(19) . ? Cu1 O1 1.919(2) . ? Cu1 O1 1.919(2) 4 ? O1 C1 1.262(4) . ? O2 C3 1.268(3) . ? O3 C1 1.231(4) . ? O4 C3 1.238(3) . ? C1 C2 1.507(4) . ? C2 C3 1.521(4) . ? N11 C11 1.480(4) . ? C11 C12 1.504(4) . ? C12 C11 1.504(4) 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 89.09(12) 4 . ? O2 Cu1 O1 170.89(13) 4 . ? O2 Cu1 O1 92.01(9) . . ? O2 Cu1 O1 92.01(9) 4 4 ? O2 Cu1 O1 170.89(13) . 4 ? O1 Cu1 O1 88.32(15) . 4 ? C1 O1 Cu1 126.6(2) . . ? C3 O2 Cu1 125.68(19) . . ? O3 C1 O1 122.2(3) . . ? O3 C1 C2 118.0(3) . . ? O1 C1 C2 119.8(3) . . ? C1 C2 C3 117.8(3) . . ? O4 C3 O2 121.1(3) . . ? O4 C3 C2 118.5(3) . . ? O2 C3 C2 120.3(3) . . ? N11 C11 C12 111.0(2) . . ? C11 C12 C11 110.7(3) . 4 ? _diffrn_measured_fraction_theta_max 0.930 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.930 _refine_diff_density_max 0.297 _refine_diff_density_min -0.580 _refine_diff_density_rms 0.070 # Attachment 'compound5.cif' data_compound5 _database_code_depnum_ccdc_archive 'CCDC 253066' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H22 Cu N2 O10' _chemical_formula_weight 393.84 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.3346(3) _cell_length_b 13.6142(3) _cell_length_c 7.9365(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.519(3) _cell_angle_gamma 90.00 _cell_volume 785.68(5) _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 'rectangular prism' _exptl_crystal_colour blue _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 410 _exptl_absorpt_coefficient_mu 1.444 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS, Sheldrick, 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 '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 4412 _diffrn_reflns_av_R_equivalents 0.0177 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 4.65 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3146 _reflns_number_gt 2680 _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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0460P)^2^+0.0294P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.611(15) _refine_ls_number_reflns 3146 _refine_ls_number_parameters 209 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0504 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0829 _refine_ls_wR_factor_gt 0.0786 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 Cu1 Cu 0.21333(5) 0.04440(4) 0.50510(5) 0.02024(12) Uani 1 1 d . . . C1 C 0.3758(5) -0.1026(3) 0.7350(5) 0.0227(8) Uani 1 1 d . . . C2 C 0.4790(5) -0.1359(3) 0.5954(5) 0.0261(9) Uani 1 1 d . . . H1 H 0.5301 -0.2004 0.6243 0.031 Uiso 1 1 calc R . . H2 H 0.5810 -0.0913 0.5893 0.031 Uiso 1 1 calc R . . C3 C 0.3675(5) -0.1415(3) 0.4226(5) 0.0232(8) Uani 1 1 d . . . O1 O 0.2789(4) -0.0258(2) 0.7159(3) 0.0284(6) Uani 1 1 d . . . O2 O 0.2724(4) -0.06589(19) 0.3692(3) 0.0269(7) Uani 1 1 d . . . O3 O 0.3886(4) -0.1515(2) 0.8707(4) 0.0406(8) Uani 1 1 d . . . O4 O 0.3707(4) -0.2172(2) 0.3361(4) 0.0385(8) Uani 1 1 d . . . C11 C 0.1232(5) 0.2437(3) 0.5838(5) 0.0222(8) Uani 1 1 d . . . C12 C 0.0245(5) 0.2466(3) 0.4024(5) 0.0227(8) Uani 1 1 d . . . H12 H -0.0907 0.2112 0.3991 0.027 Uiso 1 1 calc R . . H11 H -0.0051 0.3144 0.3729 0.027 Uiso 1 1 calc R . . C13 C 0.1306(5) 0.2039(3) 0.2684(5) 0.0204(8) Uani 1 1 d . . . O11 O 0.1872(4) 0.16051(19) 0.6399(3) 0.0286(6) Uani 1 1 d . . . O12 O 0.2176(4) 0.1238(2) 0.2997(3) 0.0269(7) Uani 1 1 d . . . O13 O 0.1391(4) 0.3176(2) 0.6701(4) 0.0351(7) Uani 1 1 d . . . O14 O 0.1304(4) 0.2480(2) 0.1338(4) 0.0347(7) Uani 1 1 d . . . C21 C 0.5289(6) 0.1155(3) 0.0243(5) 0.0336(10) Uani 1 1 d . . . H25 H 0.4533 0.0569 0.0229 0.040 Uiso 1 1 calc R . . H24 H 0.5672 0.1327 0.1421 0.040 Uiso 1 1 calc R . . C22 C 0.6959(5) 0.0924(3) -0.0580(5) 0.0282(9) Uani 1 1 d . . . H27 H 0.7731 0.1503 -0.0552 0.034 Uiso 1 1 calc R . . H26 H 0.6584 0.0754 -0.1762 0.034 Uiso 1 1 calc R . . C23 C 0.8051(6) 0.0091(3) 0.0282(5) 0.0307(10) Uani 1 1 d . . . H28 H 0.8339 0.0237 0.1484 0.037 Uiso 1 1 calc R . . H29 H 0.7312 -0.0502 0.0171 0.037 Uiso 1 1 calc R . . C24 C 0.9785(5) -0.0083(3) -0.0446(5) 0.0294(9) Uani 1 1 d . . . H31 H 1.0556 0.0497 -0.0272 0.035 Uiso 1 1 calc R . . H30 H 0.9502 -0.0189 -0.1660 0.035 Uiso 1 1 calc R . . N21 N 0.4158(5) 0.1966(3) -0.0586(4) 0.0279(8) Uani 1 1 d . . . H21 H 0.3184 0.2063 -0.0044 0.042 Uiso 1 1 calc R . . H22 H 0.3783 0.1810 -0.1665 0.042 Uiso 1 1 calc R . . H23 H 0.4827 0.2513 -0.0546 0.042 Uiso 1 1 calc R . . N22 N 1.0822(4) -0.0952(2) 0.0343(4) 0.0263(7) Uani 1 1 d . . . H34 H 1.1855 -0.1029 -0.0120 0.039 Uiso 1 1 calc R . . H33 H 1.0132 -0.1489 0.0161 0.039 Uiso 1 1 calc R . . H32 H 1.1097 -0.0855 0.1456 0.039 Uiso 1 1 calc R . . O1W O -0.0832(4) -0.0033(2) 0.4808(4) 0.0376(7) Uani 1 1 d . . . O2W O 0.6029(4) 0.1113(2) 0.4852(4) 0.0412(8) 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 0.0299(2) 0.01346(19) 0.01662(18) -0.0004(2) 0.00042(13) 0.0048(3) C1 0.0213(18) 0.023(2) 0.022(2) 0.0030(16) -0.0023(15) 0.0002(16) C2 0.0241(19) 0.025(2) 0.028(2) -0.0008(17) -0.0022(16) 0.0069(17) C3 0.025(2) 0.021(2) 0.024(2) -0.0033(16) 0.0066(16) 0.0014(17) O1 0.0400(16) 0.0241(16) 0.0213(15) 0.0065(12) 0.0047(12) 0.0171(14) O2 0.0444(17) 0.0163(16) 0.0180(15) -0.0050(12) -0.0028(13) 0.0096(13) O3 0.0477(19) 0.038(2) 0.037(2) 0.0178(16) 0.0073(15) 0.0192(16) O4 0.0567(19) 0.0232(16) 0.0348(18) -0.0083(13) 0.0031(14) 0.0131(14) C11 0.028(2) 0.018(2) 0.022(2) -0.0018(15) 0.0061(15) 0.0023(16) C12 0.0248(19) 0.0166(19) 0.026(2) 0.0042(15) -0.0002(16) 0.0046(16) C13 0.0177(17) 0.024(2) 0.018(2) 0.0010(16) -0.0028(14) -0.0002(16) O11 0.0481(17) 0.0133(15) 0.0223(16) -0.0021(11) -0.0039(13) 0.0098(13) O12 0.0366(16) 0.0249(16) 0.0198(15) 0.0009(12) 0.0054(12) 0.0113(13) O13 0.061(2) 0.0157(15) 0.0259(16) -0.0068(12) -0.0050(13) 0.0071(14) O14 0.0447(17) 0.0377(19) 0.0231(16) 0.0134(14) 0.0098(13) 0.0164(15) C21 0.036(2) 0.036(2) 0.028(2) 0.0046(19) 0.0055(18) 0.010(2) C22 0.028(2) 0.027(2) 0.030(2) 0.0086(18) 0.0065(19) 0.0051(17) C23 0.031(2) 0.033(3) 0.029(2) 0.0078(16) 0.0062(18) 0.0072(17) C24 0.0279(19) 0.028(2) 0.033(2) 0.0027(18) 0.0063(17) 0.0073(18) N21 0.0251(17) 0.0241(19) 0.033(2) -0.0048(15) -0.0020(15) -0.0003(16) N22 0.0262(16) 0.0259(19) 0.0259(18) -0.0004(14) -0.0001(13) 0.0010(15) O1W 0.0290(14) 0.0309(16) 0.051(2) -0.0079(15) -0.0011(14) -0.0017(13) O2W 0.0367(17) 0.0377(17) 0.048(2) -0.0077(15) 0.0000(14) 0.0082(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.931(3) . ? Cu1 O1 1.932(3) . ? Cu1 O11 1.932(3) . ? Cu1 O12 1.960(3) . ? Cu1 O1W 2.254(3) . ? C1 O3 1.258(5) . ? C1 O1 1.263(5) . ? C1 C2 1.491(5) . ? C2 C3 1.504(5) . ? C3 O4 1.241(5) . ? C3 O2 1.284(5) . ? C11 O13 1.215(5) . ? C11 O11 1.283(4) . ? C11 C12 1.525(5) . ? C12 C13 1.514(5) . ? C13 O14 1.225(4) . ? C13 O12 1.271(5) . ? C21 N21 1.483(5) . ? C21 C22 1.495(6) . ? C22 C23 1.500(5) . ? C23 C24 1.483(5) . ? C24 N22 1.499(5) . ? 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 O1 92.91(11) . . ? O2 Cu1 O11 172.42(13) . . ? O1 Cu1 O11 87.50(12) . . ? O2 Cu1 O12 86.28(12) . . ? O1 Cu1 O12 164.56(13) . . ? O11 Cu1 O12 91.31(12) . . ? O2 Cu1 O1W 90.71(11) . . ? O1 Cu1 O1W 93.41(12) . . ? O11 Cu1 O1W 96.82(11) . . ? O12 Cu1 O1W 102.02(12) . . ? O3 C1 O1 121.2(4) . . ? O3 C1 C2 119.1(3) . . ? O1 C1 C2 119.6(3) . . ? C1 C2 C3 115.1(3) . . ? O4 C3 O2 122.2(4) . . ? O4 C3 C2 119.9(3) . . ? O2 C3 C2 117.9(3) . . ? C1 O1 Cu1 125.9(3) . . ? C3 O2 Cu1 126.2(2) . . ? O13 C11 O11 122.1(4) . . ? O13 C11 C12 120.6(3) . . ? O11 C11 C12 117.3(3) . . ? C13 C12 C11 115.4(3) . . ? O14 C13 O12 122.3(4) . . ? O14 C13 C12 118.8(3) . . ? O12 C13 C12 118.9(3) . . ? C11 O11 Cu1 126.0(3) . . ? C13 O12 Cu1 125.0(2) . . ? N21 C21 C22 113.9(4) . . ? C21 C22 C23 112.2(3) . . ? C24 C23 C22 112.1(3) . . ? C23 C24 N22 112.2(3) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.428 _refine_diff_density_min -0.388 _refine_diff_density_rms 0.079 data_compound1b _database_code_depnum_ccdc_archive 'CCDC 601070' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H12 Cu N2 O8' _chemical_formula_weight 303.72 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 orthorhombic _symmetry_space_group_name_H-M 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2 d' _symmetry_Int_Tables_number 43 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+3/4, -y+5/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+5/4, -y+3/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+5/4, -y+5/4, z+1/4' _cell_length_a 13.6559(18) _cell_length_b 16.4436(9) _cell_length_c 9.0876(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2040.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'irregular prism' _exptl_crystal_colour 'palid blue' _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.977 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 2.178 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details '(SADABS, Sheldrick, Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 2259 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 5.13 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1076 _reflns_number_gt 1009 _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 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0153P)^2^+2.0844P] 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 0.03(2) _refine_ls_number_reflns 1076 _refine_ls_number_parameters 103 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0226 _refine_ls_wR_factor_ref 0.0508 _refine_ls_wR_factor_gt 0.0499 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.079 _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 0.43896(8) 0.00639(11) Uani 1 2 d S . . O1 O 0.21240(17) -0.17355(13) 0.2837(2) 0.0094(4) Uani 1 1 d . . . O2 O 0.21161(17) -0.17521(13) 0.59398(18) 0.0088(4) Uani 1 1 d . . . O3 O 0.13812(14) -0.06293(11) 0.2044(2) 0.0083(4) Uani 1 1 d . . . O4 O 0.16410(12) -0.05815(10) 0.6902(3) 0.0085(4) Uani 1 1 d . . . C1 C 0.1857(2) -0.10092(19) 0.3011(3) 0.0074(6) Uani 1 1 d . . . C2 C 0.2137(2) -0.05474(15) 0.4397(4) 0.0076(5) Uani 1 1 d . . . C3 C 0.1946(2) -0.09963(19) 0.5834(3) 0.0063(6) Uani 1 1 d . . . N11 N 0.17996(17) -0.15024(13) -0.0555(4) 0.0093(4) Uani 1 1 d . . . H11 H 0.161(3) -0.123(3) 0.031(5) 0.038(13) Uiso 1 1 d . . . H12 H 0.148(2) -0.200(2) -0.068(5) 0.027(9) Uiso 1 1 d . . . H13 H 0.171(3) -0.121(3) -0.136(5) 0.028(12) Uiso 1 1 d . . . H14 H 0.245(2) -0.1608(17) -0.036(4) 0.009(8) Uiso 1 1 d . . . H1 H 0.185(2) -0.0033(15) 0.442(3) 0.005(7) Uiso 1 1 d . . . H2 H 0.283(2) -0.0460(17) 0.429(6) 0.008(7) 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 Cu1 0.00982(19) 0.00514(18) 0.00420(17) 0.000 0.000 0.0017(2) O1 0.0141(11) 0.0073(11) 0.0068(10) -0.0001(8) 0.0003(9) 0.0031(10) O2 0.0129(11) 0.0066(11) 0.0069(10) 0.0006(8) 0.0013(9) 0.0019(10) O3 0.0095(9) 0.0106(9) 0.0050(10) 0.0014(10) 0.0005(9) 0.0040(7) O4 0.0108(9) 0.0084(8) 0.0063(8) -0.0006(10) -0.0003(10) 0.0018(7) C1 0.0046(13) 0.0089(15) 0.0086(14) -0.0002(12) 0.0037(12) -0.0017(12) C2 0.0106(11) 0.0047(11) 0.0076(11) 0.0010(14) -0.0007(16) -0.0012(10) C3 0.0042(14) 0.0091(15) 0.0055(13) 0.0000(11) -0.0014(11) -0.0032(12) N11 0.0109(11) 0.0097(10) 0.0073(11) 0.0023(12) 0.0001(12) -0.0019(10) _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 1.942(2) 14_545 ? Cu1 O2 1.942(2) . ? Cu1 O1 1.958(2) 14_545 ? Cu1 O1 1.958(2) . ? Cu1 O4 2.4365(17) 12_444 ? Cu1 O4 2.4365(17) 7_544 ? O1 C1 1.259(3) . ? O2 C3 1.268(4) . ? O3 C1 1.259(4) . ? O4 C3 1.257(4) . ? O4 Cu1 2.4365(17) 3 ? C1 C2 1.519(4) . ? C2 C3 1.523(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 87.00(12) 14_545 . ? O2 Cu1 O1 92.60(6) 14_545 14_545 ? O2 Cu1 O1 179.27(11) . 14_545 ? O2 Cu1 O1 179.27(11) 14_545 . ? O2 Cu1 O1 92.60(6) . . ? O1 Cu1 O1 87.81(12) 14_545 . ? O2 Cu1 O4 89.82(8) 14_545 12_444 ? O2 Cu1 O4 89.80(9) . 12_444 ? O1 Cu1 O4 90.81(9) 14_545 12_444 ? O1 Cu1 O4 89.57(9) . 12_444 ? O2 Cu1 O4 89.80(9) 14_545 7_544 ? O2 Cu1 O4 89.82(8) . 7_544 ? O1 Cu1 O4 89.57(9) 14_545 7_544 ? O1 Cu1 O4 90.81(9) . 7_544 ? O4 Cu1 O4 179.47(13) 12_444 7_544 ? C1 O1 Cu1 126.48(18) . . ? C3 O2 Cu1 127.95(17) . . ? C3 O4 Cu1 120.93(19) . 3 ? O3 C1 O1 122.2(3) . . ? O3 C1 C2 117.4(3) . . ? O1 C1 C2 120.4(2) . . ? C1 C2 C3 115.2(2) . . ? O4 C3 O2 122.3(3) . . ? O4 C3 C2 117.1(3) . . ? O2 C3 C2 120.6(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.328 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.076