# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _publ_contact_author_email MIGUEL.JULVE@UV.ES _publ_contact_author_name 'Prof M Julve' _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 _publ_contact_author_address ; Departament de Quimica Inorganica Facultat de Quimica de la Universitat de Valencia Dr.Moliner, 50 Valencia Burjassot 46100 SPAIN ; _publ_section_title ; Syntheses, Crystal Structures and Magnetic Properties of New Oxalato-, Croconato- and Squarato-Containing Copper(II) Complexes ; loop_ _publ_author_name 'M. Julve' 'Conor Brennan' 'José Carranza' 'F. Lloret' 'Paul Rillema' 'Jorunn Sletten' ; B.Vangdal ; data_1JC _database_code_CSD 200154 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 Cu N3 O7' _chemical_formula_weight 350.77 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.0936(6) _cell_length_b 9.8281(6) _cell_length_c 10.1197(8) _cell_angle_alpha 80.231(2) _cell_angle_beta 81.306(3) _cell_angle_gamma 71.641(3) _cell_volume 656.28(9) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3109 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour 'light blue' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.775 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 358 _exptl_absorpt_coefficient_mu 1.703 _exptl_absorpt_correction_type 'empirical, sadabs' _exptl_absorpt_correction_T_min 'Tmin/Tmax ratio 0.882166' _exptl_absorpt_correction_T_max 'see line above' _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 '2K SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '50 first frames remeasured at end of experiment' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3 _diffrn_reflns_number 5501 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0402 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 29.16 _reflns_number_total 3501 _reflns_number_gt 2939 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, version 5.054' _computing_cell_refinement 'SAINT, version 6.02a' _computing_data_reduction 'SAINT, version 6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, version 5.1' _computing_publication_material ? _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^)+(0.0304P)^2^+0.2430P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom if bound to C or N, difmap if bound to O' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3501 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0305 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0688 _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 Cu1 Cu 0.33761(3) 0.38057(3) 0.34548(2) 0.01614(7) Uani 1 1 d . . . O1 O 0.2677(2) 0.49257(14) 0.49823(12) 0.0177(3) Uani 1 1 d . . . O2 O 0.3284(2) 0.46852(15) 0.71223(13) 0.0242(3) Uani 1 1 d . . . O3 O 0.5699(2) 0.19092(16) 0.68463(14) 0.0258(3) Uani 1 1 d . . . O4 O 0.5094(2) 0.23203(14) 0.46764(13) 0.0203(3) Uani 1 1 d . . . O5 O 0.0785(2) 0.28351(15) 0.40973(14) 0.0222(3) Uani 1 1 d . . . H51 H -0.0399 0.3432 0.4200 0.033 Uiso 1 1 d R . . H52 H 0.0773 0.2176 0.3620 0.033 Uiso 1 1 d R . . O6 O 0.8935(2) -0.05836(16) 0.72141(15) 0.0276(3) Uani 1 1 d . . . H61 H 0.9812 -0.0237 0.6804 0.041 Uiso 1 1 d R . . H62 H 0.7914 0.0144 0.6985 0.041 Uiso 1 1 d R . . O7 O 0.7779(2) -0.02705(16) 0.39465(14) 0.0271(3) Uani 1 1 d . . . H71 H 0.8055 -0.0963 0.4569 0.041 Uiso 1 1 d R . . H72 H 0.6940 0.0497 0.4154 0.041 Uiso 1 1 d R . . N1 N 0.1989(2) 0.54724(17) 0.21350(15) 0.0163(3) Uani 1 1 d . . . N2 N 0.4280(2) 0.28506(17) 0.18029(15) 0.0172(3) Uani 1 1 d . . . N3 N 0.4311(2) 0.30605(17) -0.04051(15) 0.0170(3) Uani 1 1 d . . . H31 H 0.4082 0.3439 -0.1239 0.025 Uiso 1 1 calc R . . C1 C 0.0776(3) 0.6766(2) 0.24211(19) 0.0215(4) Uani 1 1 d . . . H1 H 0.0558 0.6967 0.3327 0.032 Uiso 1 1 calc R . . C2 C -0.0168(3) 0.7816(2) 0.1444(2) 0.0241(4) Uani 1 1 d . . . H2 H -0.1035 0.8717 0.1676 0.036 Uiso 1 1 calc R . . C3 C 0.0172(3) 0.7532(2) 0.0117(2) 0.0229(4) Uani 1 1 d . . . H3 H -0.0456 0.8242 -0.0571 0.034 Uiso 1 1 calc R . . C4 C 0.1436(3) 0.6201(2) -0.01993(18) 0.0193(4) Uani 1 1 d . . . H4 H 0.1688 0.5987 -0.1102 0.029 Uiso 1 1 calc R . . C5 C 0.2318(3) 0.5197(2) 0.08329(17) 0.0155(4) Uani 1 1 d . . . C6 C 0.3632(3) 0.3737(2) 0.07014(17) 0.0153(3) Uani 1 1 d . . . C7 C 0.5390(3) 0.1556(2) 0.13818(19) 0.0209(4) Uani 1 1 d . . . H7 H 0.6035 0.0713 0.1947 0.031 Uiso 1 1 calc R . . C8 C 0.5420(3) 0.1677(2) 0.00049(18) 0.0202(4) Uani 1 1 d . . . H8 H 0.6081 0.0943 -0.0552 0.030 Uiso 1 1 calc R . . C9 C 0.3516(3) 0.4213(2) 0.60350(18) 0.0166(4) Uani 1 1 d . . . C10 C 0.4900(3) 0.2669(2) 0.58683(18) 0.0178(4) 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 0.02086(13) 0.01652(12) 0.00879(10) -0.00296(8) -0.00211(8) -0.00143(9) O1 0.0216(7) 0.0176(7) 0.0111(6) -0.0035(5) -0.0026(5) -0.0007(5) O2 0.0342(8) 0.0227(7) 0.0118(6) -0.0060(5) -0.0044(6) 0.0000(6) O3 0.0303(8) 0.0248(8) 0.0163(7) -0.0036(6) -0.0076(6) 0.0034(6) O4 0.0239(7) 0.0194(7) 0.0135(6) -0.0050(5) -0.0036(5) 0.0017(6) O5 0.0209(7) 0.0199(7) 0.0240(7) -0.0057(6) -0.0004(5) -0.0027(6) O6 0.0301(8) 0.0229(8) 0.0275(8) -0.0026(6) -0.0052(6) -0.0040(6) O7 0.0325(8) 0.0228(8) 0.0196(7) -0.0017(6) -0.0024(6) 0.0000(6) N1 0.0182(8) 0.0182(8) 0.0117(7) -0.0031(6) -0.0010(6) -0.0041(6) N2 0.0196(8) 0.0180(8) 0.0126(7) -0.0046(6) -0.0012(6) -0.0027(6) N3 0.0203(8) 0.0196(8) 0.0107(7) -0.0038(6) -0.0017(6) -0.0044(6) C1 0.0246(10) 0.0214(10) 0.0177(9) -0.0066(7) -0.0010(7) -0.0040(8) C2 0.0265(11) 0.0203(10) 0.0214(10) -0.0051(8) -0.0020(8) -0.0004(8) C3 0.0256(10) 0.0224(10) 0.0191(9) -0.0021(8) -0.0044(8) -0.0041(8) C4 0.0227(10) 0.0241(10) 0.0122(8) -0.0021(7) -0.0029(7) -0.0080(8) C5 0.0164(9) 0.0195(9) 0.0122(8) -0.0040(7) -0.0012(6) -0.0065(7) C6 0.0172(9) 0.0192(9) 0.0103(8) -0.0031(7) -0.0010(6) -0.0063(7) C7 0.0240(10) 0.0176(9) 0.0169(9) -0.0038(7) -0.0011(7) 0.0000(8) C8 0.0242(10) 0.0196(10) 0.0157(9) -0.0053(7) 0.0000(7) -0.0044(8) C9 0.0178(9) 0.0174(9) 0.0136(8) -0.0033(7) -0.0003(7) -0.0038(7) C10 0.0192(9) 0.0201(10) 0.0126(8) -0.0032(7) -0.0012(7) -0.0036(8) _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 1.9618(13) . ? Cu1 O4 1.9666(13) . ? Cu1 N2 1.9789(15) . ? Cu1 N1 2.0186(16) . ? Cu1 O5 2.2896(14) . ? Cu1 O2 3.1072(15) 2_666 ? O1 C9 1.287(2) . ? O2 C9 1.234(2) . ? O3 C10 1.229(2) . ? O4 C10 1.285(2) . ? O5 H51 0.8633 . ? O5 H52 0.8739 . ? O6 H61 0.8265 . ? O6 H62 0.8703 . ? O7 H71 0.8405 . ? O7 H72 0.8373 . ? N1 C1 1.342(2) . ? N1 C5 1.361(2) . ? N2 C6 1.337(2) . ? N2 C7 1.368(2) . ? N3 C6 1.348(2) . ? N3 C8 1.369(2) . ? N3 H31 0.8800 . ? C1 C2 1.382(3) . ? C1 H1 0.9500 . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C3 C4 1.390(3) . ? C3 H3 0.9500 . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 C6 1.459(3) . ? C7 C8 1.376(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.547(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 O4 84.19(5) . . ? O1 Cu1 N2 172.56(6) . . ? O4 Cu1 N2 97.98(6) . . ? O1 Cu1 N1 94.64(6) . . ? O4 Cu1 N1 170.57(6) . . ? N2 Cu1 N1 82.04(6) . . ? O1 Cu1 O5 92.92(5) . . ? O4 Cu1 O5 91.90(5) . . ? N2 Cu1 O5 94.12(6) . . ? N1 Cu1 O5 97.51(6) . . ? O1 Cu1 O2 80.35(5) . 2_666 ? O4 Cu1 O2 87.46(5) . 2_666 ? N2 Cu1 O2 92.61(5) . 2_666 ? N1 Cu1 O2 83.12(5) . 2_666 ? O5 Cu1 O2 173.27(4) . 2_666 ? C9 O1 Cu1 112.62(12) . . ? C10 O4 Cu1 112.99(12) . . ? Cu1 O5 H51 117.1 . . ? Cu1 O5 H52 114.8 . . ? H51 O5 H52 109.4 . . ? H61 O6 H62 97.1 . . ? H71 O7 H72 116.8 . . ? C1 N1 C5 118.66(16) . . ? C1 N1 Cu1 126.93(12) . . ? C5 N1 Cu1 114.39(13) . . ? C6 N2 C7 106.55(15) . . ? C6 N2 Cu1 112.23(12) . . ? C7 N2 Cu1 141.22(13) . . ? C6 N3 C8 107.55(15) . . ? C6 N3 H31 126.2 . . ? C8 N3 H31 126.2 . . ? N1 C1 C2 122.28(17) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 118.93(19) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.56(19) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.38(17) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 122.19(17) . . ? N1 C5 C6 111.66(15) . . ? C4 C5 C6 126.12(16) . . ? N2 C6 N3 110.56(16) . . ? N2 C6 C5 119.59(15) . . ? N3 C6 C5 129.82(16) . . ? N2 C7 C8 108.77(17) . . ? N2 C7 H7 125.6 . . ? C8 C7 H7 125.6 . . ? N3 C8 C7 106.57(17) . . ? N3 C8 H8 126.7 . . ? C7 C8 H8 126.7 . . ? O2 C9 O1 124.44(18) . . ? O2 C9 C10 120.12(16) . . ? O1 C9 C10 115.44(15) . . ? O3 C10 O4 126.53(18) . . ? O3 C10 C9 118.95(16) . . ? O4 C10 C9 114.52(15) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 29.16 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.420 _refine_diff_density_min -0.464 _refine_diff_density_rms 0.074 #===END data_2jc _database_code_CSD 200155 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H15 Cu N3 O8' _chemical_formula_weight 392.81 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' 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 8.4848(4) _cell_length_b 21.1731(12) _cell_length_c 9.3035(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.533(2) _cell_angle_gamma 90.00 _cell_volume 1554.72(14) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8132 _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour green _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 1.453 _exptl_absorpt_correction_type 'empirical, SADABS' _exptl_absorpt_correction_T_min 'Tmin/Tmax ratio 0.830281' _exptl_absorpt_correction_T_max 'see above' _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 '2K SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '50 first frames remeasured at end of data collection' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13985 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 30.52 _reflns_number_total 4716 _reflns_number_gt 4093 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, version 5.054' _computing_cell_refinement 'SAINT, version 6.02a' _computing_data_reduction 'SAINT, version 6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, version 5.1' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.1883P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom if bound to C or N, difmap if bound to O' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4716 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0263 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0748 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 0.41859(2) 0.656775(7) 0.10438(2) 0.01757(6) Uani 1 1 d . . . O1 O 0.27046(14) 0.68661(5) 0.20983(13) 0.0230(2) Uani 1 1 d . . . O2 O 0.15639(14) 0.54149(5) 0.24602(14) 0.0272(2) Uani 1 1 d . . . O3 O -0.09049(14) 0.59630(5) 0.41600(13) 0.0268(2) Uani 1 1 d . . . O4 O 0.00869(14) 0.73912(5) 0.35671(14) 0.0267(2) Uani 1 1 d . . . O5 O 0.39177(14) 0.56533(5) 0.13103(14) 0.0243(2) Uani 1 1 d . . . H51 H 0.3250 0.5555 0.1624 0.036 Uiso 1 1 d R . . H52 H 0.4827 0.5446 0.1841 0.036 Uiso 1 1 d R . . O6 O 0.22067(14) 0.66133(5) -0.12892(13) 0.0238(2) Uani 1 1 d . . . H61 H 0.1554 0.6906 -0.1381 0.036 Uiso 1 1 d R . . H62 H 0.1663 0.6285 -0.1581 0.036 Uiso 1 1 d R . . O7 O 0.67565(15) 0.50371(6) 0.29203(16) 0.0328(3) Uani 1 1 d . . . H71 H 0.7236 0.4814 0.2578 0.049 Uiso 1 1 d R . . H72 H 0.7416 0.5334 0.3180 0.051 Uiso 1 1 d R . . O8 O -0.03299(15) 0.44125(5) 0.27464(14) 0.0275(2) Uani 1 1 d . . . H81 H 0.0034 0.4326 0.3587 0.041 Uiso 1 1 d R . . H82 H 0.0329 0.4711 0.2795 0.041 Uiso 1 1 d R . . N1 N 0.48949(15) 0.74886(5) 0.09709(14) 0.0182(2) Uani 1 1 d . . . N2 N 0.61251(15) 0.64215(6) 0.03615(14) 0.0192(2) Uani 1 1 d . . . N3 N 0.79984(15) 0.68466(6) -0.04875(14) 0.0207(2) Uani 1 1 d . . . H31 H 0.8598 0.7132 -0.0750 0.031 Uiso 1 1 calc R . . C1 C 0.41851(18) 0.80084(7) 0.13126(17) 0.0210(3) Uani 1 1 d . . . H1 H 0.3314 0.7960 0.1717 0.031 Uiso 1 1 calc R . . C2 C 0.4691(2) 0.86138(7) 0.10895(17) 0.0241(3) Uani 1 1 d . . . H2 H 0.4168 0.8973 0.1337 0.036 Uiso 1 1 calc R . . C3 C 0.5961(2) 0.86888(7) 0.05044(19) 0.0262(3) Uani 1 1 d . . . H3 H 0.6315 0.9099 0.0340 0.039 Uiso 1 1 calc R . . C4 C 0.67140(19) 0.81553(7) 0.01594(18) 0.0235(3) Uani 1 1 d . . . H4 H 0.7597 0.8194 -0.0234 0.035 Uiso 1 1 calc R . . C5 C 0.61436(17) 0.75651(6) 0.04036(16) 0.0181(2) Uani 1 1 d . . . C6 C 0.67846(17) 0.69611(6) 0.00911(16) 0.0183(2) Uani 1 1 d . . . C7 C 0.69622(18) 0.59401(7) -0.00651(17) 0.0217(3) Uani 1 1 d . . . H7 H 0.6764 0.5501 -0.0003 0.032 Uiso 1 1 calc R . . C8 C 0.81271(19) 0.62009(7) -0.05926(17) 0.0227(3) Uani 1 1 d . . . H8 H 0.8878 0.5979 -0.0960 0.034 Uiso 1 1 calc R . . C9 C 0.16843(17) 0.65991(6) 0.26105(16) 0.0175(2) Uani 1 1 d . . . C10 C 0.11805(17) 0.59538(7) 0.28053(16) 0.0194(2) Uani 1 1 d . . . C11 C 0.00474(17) 0.61996(7) 0.35463(16) 0.0195(3) Uani 1 1 d . . . C12 C 0.05145(17) 0.68490(7) 0.33018(16) 0.0191(2) 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 0.01871(10) 0.01494(9) 0.02365(10) -0.00034(6) 0.01320(7) -0.00086(6) O1 0.0287(5) 0.0175(5) 0.0324(5) -0.0011(4) 0.0224(5) -0.0016(4) O2 0.0299(6) 0.0159(5) 0.0453(7) -0.0008(4) 0.0250(5) -0.0012(4) O3 0.0275(6) 0.0272(5) 0.0339(6) 0.0009(4) 0.0208(5) -0.0038(4) O4 0.0286(6) 0.0187(5) 0.0412(6) -0.0056(4) 0.0228(5) -0.0010(4) O5 0.0239(5) 0.0174(5) 0.0390(6) 0.0028(4) 0.0204(5) 0.0011(4) O6 0.0234(5) 0.0183(5) 0.0291(5) -0.0014(4) 0.0088(4) 0.0006(4) O7 0.0259(6) 0.0250(6) 0.0510(8) 0.0033(5) 0.0182(5) 0.0001(4) O8 0.0309(6) 0.0224(5) 0.0308(6) -0.0019(4) 0.0131(5) -0.0070(4) N1 0.0196(5) 0.0170(5) 0.0208(5) -0.0008(4) 0.0108(4) -0.0012(4) N2 0.0202(5) 0.0182(5) 0.0227(6) -0.0006(4) 0.0120(5) -0.0006(4) N3 0.0194(5) 0.0232(6) 0.0237(6) -0.0004(4) 0.0130(5) -0.0009(4) C1 0.0208(6) 0.0210(7) 0.0238(7) -0.0012(5) 0.0113(5) 0.0011(5) C2 0.0265(7) 0.0194(7) 0.0262(7) -0.0025(5) 0.0096(6) 0.0008(5) C3 0.0304(8) 0.0185(7) 0.0312(7) -0.0002(5) 0.0132(6) -0.0034(6) C4 0.0241(7) 0.0214(7) 0.0280(7) 0.0009(5) 0.0132(6) -0.0033(5) C5 0.0174(6) 0.0194(6) 0.0195(6) -0.0004(5) 0.0090(5) -0.0018(5) C6 0.0174(6) 0.0202(6) 0.0200(6) -0.0001(5) 0.0102(5) -0.0005(5) C7 0.0234(7) 0.0197(6) 0.0243(7) -0.0008(5) 0.0115(5) 0.0011(5) C8 0.0229(7) 0.0251(7) 0.0233(7) -0.0026(5) 0.0121(5) 0.0018(5) C9 0.0185(6) 0.0162(6) 0.0201(6) -0.0006(4) 0.0098(5) -0.0004(4) C10 0.0181(6) 0.0188(6) 0.0238(6) 0.0006(5) 0.0105(5) -0.0007(5) C11 0.0184(6) 0.0206(6) 0.0220(6) 0.0001(5) 0.0102(5) -0.0006(5) C12 0.0182(6) 0.0197(6) 0.0218(6) -0.0017(5) 0.0103(5) -0.0021(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 1.9612(10) . ? Cu1 O5 1.9758(10) . ? Cu1 N2 1.9932(12) . ? Cu1 N1 2.0489(11) . ? Cu1 O6 2.2057(11) . ? O1 C9 1.2645(16) . ? O2 C10 1.2600(17) . ? O3 C11 1.2524(17) . ? O4 C12 1.2553(17) . ? O5 H51 0.7552 . ? O5 H52 0.8665 . ? O6 H61 0.8141 . ? O6 H62 0.8236 . ? O7 H71 0.7647 . ? O7 H72 0.8164 . ? O8 H81 0.7510 . ? O8 H82 0.8337 . ? N1 C1 1.3473(17) . ? N1 C5 1.3557(17) . ? N2 C6 1.3360(17) . ? N2 C7 1.3814(18) . ? N3 C6 1.3476(16) . ? N3 C8 1.378(2) . ? N3 H31 0.8800 . ? C1 C2 1.391(2) . ? C1 H1 0.9500 . ? C2 C3 1.384(2) . ? C2 H2 0.9500 . ? C3 C4 1.392(2) . ? C3 H3 0.9500 . ? C4 C5 1.3885(19) . ? C4 H4 0.9500 . ? C5 C6 1.4601(19) . ? C7 C8 1.371(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.4626(18) . ? C9 C12 1.4654(18) . ? C10 C11 1.4687(19) . ? C11 C12 1.472(2) . ? 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 O5 97.37(4) . . ? O1 Cu1 N2 164.76(5) . . ? O5 Cu1 N2 91.97(5) . . ? O1 Cu1 N1 87.70(4) . . ? O5 Cu1 N1 170.22(5) . . ? N2 Cu1 N1 81.40(5) . . ? O1 Cu1 O6 94.70(4) . . ? O5 Cu1 O6 94.89(4) . . ? N2 Cu1 O6 96.47(5) . . ? N1 Cu1 O6 93.01(4) . . ? C9 O1 Cu1 134.24(9) . . ? Cu1 O5 H51 117.0 . . ? Cu1 O5 H52 116.6 . . ? H51 O5 H52 106.2 . . ? Cu1 O6 H61 112.3 . . ? Cu1 O6 H62 114.8 . . ? H61 O6 H62 109.3 . . ? H71 O7 H72 100.9 . . ? H81 O8 H82 96.7 . . ? C1 N1 C5 118.37(12) . . ? C1 N1 Cu1 127.40(9) . . ? C5 N1 Cu1 114.05(9) . . ? C6 N2 C7 106.37(12) . . ? C6 N2 Cu1 112.27(9) . . ? C7 N2 Cu1 141.05(10) . . ? C6 N3 C8 107.40(11) . . ? C6 N3 H31 126.3 . . ? C8 N3 H31 126.3 . . ? N1 C1 C2 121.89(13) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C3 C2 C1 119.47(14) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C2 C3 C4 119.16(14) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 118.40(13) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 122.71(12) . . ? N1 C5 C6 111.98(11) . . ? C4 C5 C6 125.31(12) . . ? N2 C6 N3 110.83(12) . . ? N2 C6 C5 119.94(12) . . ? N3 C6 C5 129.22(12) . . ? C8 C7 N2 108.66(13) . . ? C8 C7 H7 125.7 . . ? N2 C7 H7 125.7 . . ? C7 C8 N3 106.74(12) . . ? C7 C8 H8 126.6 . . ? N3 C8 H8 126.6 . . ? O1 C9 C10 137.39(12) . . ? O1 C9 C12 132.19(12) . . ? C10 C9 C12 90.41(10) . . ? O2 C10 C9 134.42(12) . . ? O2 C10 C11 135.66(13) . . ? C9 C10 C11 89.92(11) . . ? O3 C11 C10 135.67(14) . . ? O3 C11 C12 134.39(13) . . ? C10 C11 C12 89.93(10) . . ? O4 C12 C9 135.05(13) . . ? O4 C12 C11 135.26(12) . . ? C9 C12 C11 89.69(11) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.395 _refine_diff_density_min -0.549 _refine_diff_density_rms 0.128 #===END data_22jc _database_code_CSD 200156 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 Cu N4 O6' _chemical_formula_weight 321.74 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9893(4) _cell_length_b 9.2227(5) _cell_length_c 9.8112(5) _cell_angle_alpha 102.2660(10) _cell_angle_beta 106.7790(10) _cell_angle_gamma 103.5270(10) _cell_volume 561.45(5) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 3274 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 29 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.903 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 1.978 _exptl_absorpt_correction_type 'empirical, SADABS' _exptl_absorpt_correction_T_min 'Tmin/tmax ratio 0.798486' _exptl_absorpt_correction_T_max 'see above' _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 '2K SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '50 first frames remeasured at end of experiment' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 4689 _diffrn_reflns_av_R_equivalents 0.0176 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 29.01 _reflns_number_total 2979 _reflns_number_gt 2556 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, version 5.054' _computing_cell_refinement 'SAINT, version 6.02A' _computing_data_reduction 'SAINT, version 6.02A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, version 5.1' _computing_publication_material 'XCIF, version 5.10' _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^)+(0.0282P)^2^+0.2590P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom if bound to C or N, difmap if bound to O' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2979 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.27885(4) 0.15141(3) -0.12490(3) 0.01582(8) Uani 1 1 d . . . O1 O 0.2063(2) 0.30218(17) 0.00704(16) 0.0189(3) Uani 1 1 d . . . O2 O 0.2476(2) 0.02681(17) 0.01143(15) 0.0176(3) Uani 1 1 d . . . O3 O 0.2304(3) 0.06206(18) 0.23984(16) 0.0226(3) Uani 1 1 d . . . O4 O 0.1752(3) 0.34708(18) 0.23130(16) 0.0223(3) Uani 1 1 d . . . O5 O 0.6284(2) 0.23980(17) -0.00706(16) 0.0197(3) Uani 1 1 d . . . H51 H 0.6667 0.1634 -0.0176 0.029(7) Uiso 1 1 d R . . H52 H 0.6850 0.2780 -0.0671 0.043(8) Uiso 1 1 d R . . O6 O 0.8457(3) 0.36457(19) -0.17126(17) 0.0248(3) Uani 1 1 d . . . H61 H 0.9663 0.3671 -0.1243 0.044(9) Uiso 1 1 d R . . H62 H 0.8608 0.4536 -0.1839 0.049(9) Uiso 1 1 d R . . N1 N 0.2521(3) -0.0204(2) -0.30133(19) 0.0168(3) Uani 1 1 d . . . N2 N 0.2910(3) 0.2781(2) -0.26408(18) 0.0165(3) Uani 1 1 d . . . N3 N 0.2903(3) 0.2845(2) -0.48730(19) 0.0193(4) Uani 1 1 d . . . H31 H 0.2849 0.2546 -0.5779 0.057(10) Uiso 1 1 calc R . . N4 N 0.2389(3) -0.0833(2) -0.53419(19) 0.0177(4) Uani 1 1 d . . . H41 H 0.2394 -0.0746 -0.6197 0.038(8) Uiso 1 1 calc R . . C1 C 0.2007(3) 0.2662(2) 0.1252(2) 0.0164(4) Uani 1 1 d . . . C2 C 0.2290(3) 0.1039(2) 0.1289(2) 0.0167(4) Uani 1 1 d . . . C3 C 0.3131(3) 0.4291(2) -0.2696(2) 0.0198(4) Uani 1 1 d . . . H3 H 0.3262 0.5136 -0.1924 0.026(7) Uiso 1 1 calc R . . C4 C 0.3124(4) 0.4329(3) -0.4077(2) 0.0227(5) Uani 1 1 d . . . H4 H 0.3246 0.5201 -0.4418 0.023(6) Uiso 1 1 calc R . . C5 C 0.2788(3) 0.1953(2) -0.3970(2) 0.0153(4) Uani 1 1 d . . . C6 C 0.2575(3) 0.0315(2) -0.4173(2) 0.0159(4) Uani 1 1 d . . . C7 C 0.2271(3) -0.1778(2) -0.3484(2) 0.0200(4) Uani 1 1 d . . . H7 H 0.2173 -0.2458 -0.2911 0.021(6) Uiso 1 1 calc R . . C8 C 0.2190(4) -0.2179(3) -0.4929(2) 0.0205(4) Uani 1 1 d . . . H8 H 0.2032 -0.3166 -0.5515 0.020(6) 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 0.02306(14) 0.01758(13) 0.01114(12) 0.00697(9) 0.00821(10) 0.00913(10) O1 0.0296(8) 0.0197(7) 0.0148(7) 0.0092(6) 0.0115(6) 0.0134(7) O2 0.0254(8) 0.0178(7) 0.0142(7) 0.0076(6) 0.0093(6) 0.0098(6) O3 0.0341(9) 0.0257(8) 0.0150(7) 0.0121(6) 0.0122(7) 0.0125(7) O4 0.0343(9) 0.0234(8) 0.0157(7) 0.0072(6) 0.0133(7) 0.0137(7) O5 0.0223(8) 0.0195(7) 0.0199(7) 0.0075(6) 0.0080(6) 0.0094(6) O6 0.0287(9) 0.0259(9) 0.0232(8) 0.0105(7) 0.0095(7) 0.0116(7) N1 0.0213(9) 0.0183(8) 0.0144(8) 0.0066(7) 0.0080(7) 0.0090(7) N2 0.0218(9) 0.0169(8) 0.0127(8) 0.0056(7) 0.0075(7) 0.0069(7) N3 0.0261(9) 0.0222(9) 0.0133(8) 0.0083(7) 0.0098(7) 0.0083(8) N4 0.0211(9) 0.0212(9) 0.0124(8) 0.0052(7) 0.0067(7) 0.0088(7) C1 0.0178(10) 0.0200(10) 0.0131(9) 0.0061(8) 0.0056(8) 0.0077(8) C2 0.0166(9) 0.0198(10) 0.0140(9) 0.0061(8) 0.0049(8) 0.0062(8) C3 0.0255(11) 0.0162(10) 0.0182(10) 0.0057(8) 0.0076(9) 0.0074(9) C4 0.0313(12) 0.0185(10) 0.0212(11) 0.0096(9) 0.0104(9) 0.0084(9) C5 0.0175(9) 0.0169(9) 0.0127(9) 0.0059(7) 0.0055(8) 0.0060(8) C6 0.0166(9) 0.0193(10) 0.0130(9) 0.0052(8) 0.0057(8) 0.0072(8) C7 0.0267(11) 0.0178(10) 0.0181(10) 0.0074(8) 0.0085(9) 0.0094(9) C8 0.0265(11) 0.0187(10) 0.0188(10) 0.0055(8) 0.0083(9) 0.0115(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 1.9521(14) . ? Cu1 O2 1.9651(13) . ? Cu1 N2 1.9836(16) . ? Cu1 N1 2.0127(17) . ? Cu1 O5 2.2378(15) . ? Cu1 O3 3.3583(17) 2 ? O1 C1 1.281(2) . ? O2 C2 1.278(2) . ? O3 C2 1.228(2) . ? O4 C1 1.229(2) . ? O5 H51 0.8068 . ? O5 H52 0.8852 . ? O6 H61 0.8282 . ? O6 H62 0.8433 . ? N1 C6 1.331(2) . ? N1 C7 1.379(3) . ? N2 C5 1.332(2) . ? N2 C3 1.380(3) . ? N3 C5 1.337(2) . ? N3 C4 1.373(3) . ? N3 H31 0.8600 . ? N4 C6 1.337(2) . ? N4 C8 1.375(3) . ? N4 H41 0.8600 . ? C1 C2 1.562(3) . ? C3 C4 1.361(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C5 C6 1.447(3) . ? C7 C8 1.367(3) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O2 84.36(6) . . ? O1 Cu1 N2 93.34(6) . . ? O2 Cu1 N2 176.14(7) . . ? O1 Cu1 N1 160.90(7) . . ? O2 Cu1 N1 98.64(6) . . ? N2 Cu1 N1 82.54(7) . . ? O1 Cu1 O5 98.11(6) . . ? O2 Cu1 O5 90.58(6) . . ? N2 Cu1 O5 92.81(6) . . ? N1 Cu1 O5 100.70(6) . . ? O1 Cu1 O3 85.00(5) . 2 ? O2 Cu1 O3 71.80(5) . 2 ? N2 Cu1 O3 104.95(6) . 2 ? N1 Cu1 O3 78.14(6) . 2 ? O5 Cu1 O3 161.80(4) . 2 ? C1 O1 Cu1 112.74(13) . . ? C2 O2 Cu1 112.40(12) . . ? Cu1 O5 H51 105.6 . . ? Cu1 O5 H52 107.5 . . ? H51 O5 H52 95.0 . . ? H61 O6 H62 104.5 . . ? C6 N1 C7 105.79(17) . . ? C6 N1 Cu1 111.68(13) . . ? C7 N1 Cu1 142.52(14) . . ? C5 N2 C3 106.34(16) . . ? C5 N2 Cu1 112.74(13) . . ? C3 N2 Cu1 140.90(14) . . ? C5 N3 C4 106.91(17) . . ? C5 N3 H31 126.5 . . ? C4 N3 H31 126.5 . . ? C6 N4 C8 107.49(17) . . ? C6 N4 H41 126.3 . . ? C8 N4 H41 126.3 . . ? O4 C1 O1 125.78(19) . . ? O4 C1 C2 119.45(17) . . ? O1 C1 C2 114.77(16) . . ? O3 C2 O2 126.51(19) . . ? O3 C2 C1 118.90(18) . . ? O2 C2 C1 114.59(16) . . ? C4 C3 N2 108.09(18) . . ? C4 C3 H3 126.0 . . ? N2 C3 H3 126.0 . . ? C3 C4 N3 107.48(18) . . ? C3 C4 H4 126.3 . . ? N3 C4 H4 126.3 . . ? N2 C5 N3 111.18(17) . . ? N2 C5 C6 116.39(17) . . ? N3 C5 C6 132.42(18) . . ? N1 C6 N4 111.37(17) . . ? N1 C6 C5 116.64(17) . . ? N4 C6 C5 131.99(18) . . ? C8 C7 N1 109.00(18) . . ? C8 C7 H7 125.5 . . ? N1 C7 H7 125.5 . . ? C7 C8 N4 106.35(18) . . ? C7 C8 H8 126.8 . . ? N4 C8 H8 126.8 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.440 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.079 #===END data_13jc _database_code_CSD 200157 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H8 Cu N4 O6' _chemical_formula_weight 379.77 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7113(4) _cell_length_b 9.2977(5) _cell_length_c 11.8250(6) _cell_angle_alpha 106.3160(10) _cell_angle_beta 97.9950(10) _cell_angle_gamma 107.8400(10) _cell_volume 653.31(6) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 4899 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 31.9 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.931 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 382 _exptl_absorpt_coefficient_mu 1.717 _exptl_absorpt_correction_type 'empirical, SADABS' _exptl_absorpt_correction_T_min 'Tmin/Tmax ratio 0.768846' _exptl_absorpt_correction_T_max 'see above' _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 '2K SMART CCD' _diffrn_measurement_method 'omega scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '50 first frames remeasured at end of experiment' _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6057 _diffrn_reflns_av_R_equivalents 0.0182 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 32.09 _reflns_number_total 4055 _reflns_number_gt 3684 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART, version 5.054' _computing_cell_refinement 'SAINT, version 6.02a' _computing_data_reduction 'SAINT, version 6.02a' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0418P)^2^+0.2473P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'geom if bound to C, difmap if bound to O' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4055 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0796 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.28156(3) 0.33018(2) 0.128467(16) 0.01612(7) Uani 1 1 d . . . O1 O 0.2735(2) 0.31781(14) -0.04131(10) 0.0209(2) Uani 1 1 d . . . O2 O 0.25147(19) 0.10108(13) 0.07398(10) 0.0178(2) Uani 1 1 d . . . O3 O 0.1892(2) -0.22139(14) -0.10683(11) 0.0227(2) Uani 1 1 d . . . O4 O 0.2568(2) -0.16268(16) -0.33368(11) 0.0274(3) Uani 1 1 d . . . O5 O 0.2829(2) 0.16962(16) -0.30445(11) 0.0261(3) Uani 1 1 d . . . O6 O 0.6384(2) 0.44450(15) 0.19363(11) 0.0239(2) Uani 1 1 d . . . H61 H 0.6985 0.5194 0.2681 0.029 Uiso 1 1 d R . . H62 H 0.7003 0.3822 0.1798 0.029 Uiso 1 1 d R . . N1 N 0.2412(2) 0.53992(15) 0.18235(12) 0.0157(2) Uani 1 1 d . . . N2 N 0.2537(2) 0.33825(15) 0.29494(11) 0.0152(2) Uani 1 1 d . . . N3 N 0.2135(2) 0.83872(17) 0.28714(14) 0.0225(3) Uani 1 1 d . . . N4 N 0.2339(2) 0.38872(17) 0.53513(12) 0.0199(3) Uani 1 1 d . . . C1 C 0.2342(3) 0.63532(19) 0.11715(15) 0.0185(3) Uani 1 1 d . . . H1 H 0.2394 0.6017 0.0343 0.022 Uiso 1 1 calc R . . C2 C 0.2194(3) 0.78480(19) 0.17105(16) 0.0213(3) Uani 1 1 d . . . H2 H 0.2132 0.8506 0.1231 0.026 Uiso 1 1 calc R . . C3 C 0.2201(3) 0.74117(19) 0.35153(15) 0.0205(3) Uani 1 1 d . . . H3 H 0.2164 0.7757 0.4346 0.025 Uiso 1 1 calc R . . C4 C 0.2324(2) 0.59103(17) 0.29977(14) 0.0159(3) Uani 1 1 d . . . C5 C 0.2383(2) 0.47533(17) 0.36322(13) 0.0150(3) Uani 1 1 d . . . C6 C 0.2322(2) 0.50059(18) 0.48435(14) 0.0176(3) Uani 1 1 d . . . H6 H 0.2266 0.5996 0.5322 0.021 Uiso 1 1 calc R . . C7 C 0.2444(3) 0.25164(19) 0.46501(14) 0.0197(3) Uani 1 1 d . . . H7 H 0.2422 0.1692 0.4980 0.024 Uiso 1 1 calc R . . C8 C 0.2583(3) 0.22645(18) 0.34490(14) 0.0174(3) Uani 1 1 d . . . H8 H 0.2712 0.1296 0.2984 0.021 Uiso 1 1 calc R . . C9 C 0.2640(2) 0.17741(18) -0.09911(14) 0.0165(3) Uani 1 1 d . . . C10 C 0.2493(2) 0.06235(17) -0.03930(13) 0.0152(3) Uani 1 1 d . . . C11 C 0.2266(2) -0.09125(18) -0.12466(14) 0.0169(3) Uani 1 1 d . . . C12 C 0.2528(2) -0.06316(19) -0.24124(14) 0.0187(3) Uani 1 1 d . . . C13 C 0.2680(3) 0.10684(19) -0.22641(14) 0.0181(3) 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 0.02767(11) 0.01246(9) 0.01031(10) 0.00448(7) 0.00636(7) 0.00884(7) O1 0.0350(6) 0.0156(5) 0.0138(5) 0.0060(4) 0.0074(4) 0.0102(4) O2 0.0298(6) 0.0147(5) 0.0109(5) 0.0048(4) 0.0067(4) 0.0097(4) O3 0.0333(6) 0.0160(5) 0.0205(6) 0.0053(4) 0.0093(5) 0.0111(5) O4 0.0377(7) 0.0262(6) 0.0159(6) 0.0005(5) 0.0100(5) 0.0129(5) O5 0.0362(7) 0.0314(6) 0.0151(5) 0.0122(5) 0.0090(5) 0.0130(5) O6 0.0281(6) 0.0208(5) 0.0218(6) 0.0032(4) 0.0059(5) 0.0114(5) N1 0.0200(6) 0.0140(5) 0.0142(6) 0.0057(4) 0.0046(4) 0.0065(4) N2 0.0204(6) 0.0134(5) 0.0123(5) 0.0047(4) 0.0042(4) 0.0066(4) N3 0.0282(7) 0.0184(6) 0.0268(7) 0.0107(5) 0.0103(6) 0.0123(5) N4 0.0270(7) 0.0213(6) 0.0135(6) 0.0070(5) 0.0067(5) 0.0100(5) C1 0.0220(7) 0.0179(7) 0.0172(7) 0.0088(5) 0.0043(5) 0.0072(5) C2 0.0246(7) 0.0178(7) 0.0262(8) 0.0123(6) 0.0069(6) 0.0093(6) C3 0.0276(8) 0.0160(7) 0.0204(7) 0.0059(6) 0.0091(6) 0.0101(6) C4 0.0193(6) 0.0142(6) 0.0154(7) 0.0059(5) 0.0052(5) 0.0066(5) C5 0.0179(6) 0.0140(6) 0.0140(6) 0.0053(5) 0.0052(5) 0.0060(5) C6 0.0216(7) 0.0176(6) 0.0143(6) 0.0047(5) 0.0064(5) 0.0079(5) C7 0.0269(7) 0.0189(7) 0.0161(7) 0.0093(5) 0.0054(6) 0.0091(6) C8 0.0242(7) 0.0155(6) 0.0138(6) 0.0059(5) 0.0045(5) 0.0084(5) C9 0.0213(7) 0.0162(6) 0.0126(6) 0.0061(5) 0.0044(5) 0.0066(5) C10 0.0191(6) 0.0151(6) 0.0124(6) 0.0052(5) 0.0048(5) 0.0069(5) C11 0.0192(6) 0.0165(6) 0.0146(6) 0.0034(5) 0.0045(5) 0.0074(5) C12 0.0194(7) 0.0202(7) 0.0142(7) 0.0032(5) 0.0050(5) 0.0062(5) C13 0.0210(7) 0.0208(7) 0.0118(6) 0.0046(5) 0.0043(5) 0.0075(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 1.9705(11) . ? Cu1 O2 1.9805(11) . ? Cu1 N2 1.9858(13) . ? Cu1 N1 1.9891(13) . ? Cu1 O6 2.2192(13) . ? Cu1 O3 2.9568(13) 2 ? O1 C9 1.2692(19) . ? O2 C10 1.2825(18) . ? O3 C11 1.2425(19) . ? O4 C12 1.2276(19) . ? O5 C13 1.223(2) . ? O6 H61 0.8993 . ? O6 H62 0.8048 . ? N1 C1 1.3352(19) . ? N1 C4 1.3515(19) . ? N2 C8 1.3379(19) . ? N2 C5 1.3465(19) . ? N3 C2 1.333(2) . ? N3 C3 1.345(2) . ? N4 C7 1.339(2) . ? N4 C6 1.341(2) . ? C1 C2 1.397(2) . ? C1 H1 0.9500 . ? C2 H2 0.9500 . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C4 C5 1.481(2) . ? C5 C6 1.393(2) . ? C6 H6 0.9500 . ? C7 C8 1.395(2) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.426(2) . ? C9 C13 1.471(2) . ? C10 C11 1.448(2) . ? C11 C12 1.497(2) . ? C12 C13 1.510(2) . ? 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 O2 86.71(4) . . ? O1 Cu1 N2 173.43(5) . . ? O2 Cu1 N2 94.04(5) . . ? O1 Cu1 N1 96.10(5) . . ? O2 Cu1 N1 166.99(5) . . ? N2 Cu1 N1 81.73(5) . . ? O1 Cu1 O6 95.21(5) . . ? O2 Cu1 O6 99.51(5) . . ? N2 Cu1 O6 91.10(5) . . ? N1 Cu1 O6 92.90(5) . . ? O1 Cu1 O3 97.80(4) . 2 ? O2 Cu1 O3 87.98(4) . 2 ? N2 Cu1 O3 75.72(4) . 2 ? N1 Cu1 O3 79.06(4) . 2 ? O6 Cu1 O3 165.34(4) . 2 ? C9 O1 Cu1 106.75(10) . . ? C10 O2 Cu1 105.89(9) . . ? Cu1 O6 H61 119.8 . . ? Cu1 O6 H62 114.0 . . ? H61 O6 H62 111.3 . . ? C1 N1 C4 118.61(13) . . ? C1 N1 Cu1 126.80(11) . . ? C4 N1 Cu1 114.48(10) . . ? C8 N2 C5 118.76(13) . . ? C8 N2 Cu1 126.71(10) . . ? C5 N2 Cu1 114.46(10) . . ? C2 N3 C3 116.83(14) . . ? C7 N4 C6 117.29(13) . . ? N1 C1 C2 119.84(15) . . ? N1 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? N3 C2 C1 122.63(14) . . ? N3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? N3 C3 C4 121.73(15) . . ? N3 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? N1 C4 C3 120.35(14) . . ? N1 C4 C5 114.22(13) . . ? C3 C4 C5 125.43(14) . . ? N2 C5 C6 120.16(14) . . ? N2 C5 C4 114.83(13) . . ? C6 C5 C4 125.00(13) . . ? N4 C6 C5 121.68(14) . . ? N4 C6 H6 119.2 . . ? C5 C6 H6 119.2 . . ? N4 C7 C8 121.86(14) . . ? N4 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? N2 C8 C7 120.19(14) . . ? N2 C8 H8 119.9 . . ? C7 C8 H8 119.9 . . ? O1 C9 C10 120.17(13) . . ? O1 C9 C13 129.71(14) . . ? C10 C9 C13 110.12(13) . . ? O2 C10 C9 120.36(13) . . ? O2 C10 C11 129.29(14) . . ? C9 C10 C11 110.33(13) . . ? O3 C11 C10 127.62(14) . . ? O3 C11 C12 126.37(14) . . ? C10 C11 C12 106.00(13) . . ? O4 C12 C11 125.66(15) . . ? O4 C12 C13 126.01(15) . . ? C11 C12 C13 108.32(12) . . ? O5 C13 C9 128.72(15) . . ? O5 C13 C12 126.42(15) . . ? C9 C13 C12 104.85(13) . . ? _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 32.09 _diffrn_measured_fraction_theta_full 0.888 _refine_diff_density_max 0.477 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.085 #===END