# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2007 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Dr. Stuart R. Batten' _publ_contact_author_address ; School of Chemistry Monash University 3800 Australia ; _publ_contact_author_phone '+61 3 9905 4606' _publ_contact_author_fax '+61 3 9905 4597' _publ_contact_author_email stuart.batten@sci.monash.edu.au _publ_section_title ; Solvothermal versus Bench-top Reactions: Control Over the Formation of Discrete Complexes and Coordination Polymers ; loop_ _publ_author_name _publ_author_footnote _publ_author_address A.S.R.Chesman . ; School of Chemistry Monash University 3800 Australia ; D.R.Turner . ; School of Chemistry Monash University 3800 Australia ; D.J.Price . ; School of Chemistry Monash University 3800 Australia ; B.Moubaraki . ; School of Chemistry Monash University 3800 Australia ; K.S.Murray . ; School of Chemistry Monash University 3800 Australia ; ; G.B.Deacon ; . ; School of Chemistry Monash University 3800 Australia ; S.R.Batten . ; School of Chemistry Monash University 3800 Australia ; data_C:\AC326\AC326.CIF _database_code_depnum_ccdc_archive 'CCDC 648200' _audit_creation_method SHELXL-97 _chemical_name_systematic ; di(3-amino-3-methoxy-2nitrosoacrylonitrilate)dimethanolcopper(II) ; _chemical_name_common ;di(3-amino-3-methoxy- 2nitrosoacrylonitrilate)dimethanolcopper(ii) ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 Cu1 N6 O6' _chemical_formula_sum 'C10 H16 Cu1 N6 O6' _chemical_formula_weight 379.83 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 5.3351(1) _cell_length_b 15.8068(4) _cell_length_c 9.3759(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.597(2) _cell_angle_gamma 90.00 _cell_volume 783.74(4) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 390 _exptl_absorpt_coefficient_mu 1.434 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7158 _exptl_absorpt_correction_T_max 0.8939 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9490 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0264 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.06 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1793 _reflns_number_gt 1720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1793 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0290 _refine_ls_R_factor_gt 0.0273 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0646 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _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 0.0000 0.5000 0.01484(10) Uani 1 2 d S . . O2 O 0.2539(2) 0.20976(7) 0.31554(12) 0.0181(3) Uani 1 1 d . . . O3 O 0.3501(2) 0.01968(9) 0.70020(14) 0.0190(3) Uani 1 1 d . . . O1 O -0.3162(2) 0.13390(8) 0.61660(13) 0.0202(3) Uani 1 1 d . . . N1 N -0.1440(3) 0.11573(9) 0.53921(14) 0.0147(3) Uani 1 1 d . . . N3 N 0.1927(3) 0.06831(9) 0.37721(15) 0.0157(3) Uani 1 1 d . . . C4 C 0.4271(3) 0.18552(11) 0.21567(18) 0.0204(4) Uani 1 1 d . . . H4A H 0.5648 0.1515 0.2662 0.031 Uiso 1 1 calc R . . H4B H 0.4971 0.2364 0.1763 0.031 Uiso 1 1 calc R . . H4C H 0.3362 0.1522 0.1371 0.031 Uiso 1 1 calc R . . N2 N -0.1633(3) 0.33209(10) 0.50094(18) 0.0258(3) Uani 1 1 d . . . C1 C -0.0353(3) 0.17673(10) 0.47323(17) 0.0147(3) Uani 1 1 d . . . C3 C 0.1511(3) 0.14773(10) 0.38294(16) 0.0145(3) Uani 1 1 d . . . C2 C -0.1051(3) 0.26333(11) 0.48607(18) 0.0174(3) Uani 1 1 d . . . C5 C 0.2755(4) 0.04696(13) 0.83402(19) 0.0263(4) Uani 1 1 d . . . H5A H 0.2025 -0.0008 0.8808 0.039 Uiso 1 1 calc R . . H5B H 0.1493 0.0921 0.8161 0.039 Uiso 1 1 calc R . . H5C H 0.4236 0.0683 0.8967 0.039 Uiso 1 1 calc R . . H3N H 0.297(4) 0.0520(14) 0.332(2) 0.020(5) Uiso 1 1 d . . . H3O H 0.427(5) 0.0498(16) 0.673(3) 0.026(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 0.01668(16) 0.01002(15) 0.01982(16) 0.00092(10) 0.00986(11) 0.00043(10) O2 0.0204(6) 0.0134(6) 0.0227(6) 0.0018(4) 0.0109(5) -0.0018(5) O3 0.0186(6) 0.0166(6) 0.0234(6) -0.0006(5) 0.0091(5) -0.0025(5) O1 0.0194(6) 0.0177(6) 0.0268(6) -0.0017(5) 0.0150(5) 0.0005(5) N1 0.0138(6) 0.0147(6) 0.0167(6) -0.0020(5) 0.0055(5) 0.0000(5) N3 0.0151(7) 0.0149(7) 0.0190(7) 0.0001(5) 0.0088(5) 0.0000(6) C4 0.0190(8) 0.0210(8) 0.0232(8) 0.0039(7) 0.0108(7) 0.0002(7) N2 0.0273(8) 0.0179(8) 0.0344(9) 0.0009(6) 0.0124(7) 0.0012(6) C1 0.0140(7) 0.0132(7) 0.0173(7) -0.0004(6) 0.0037(6) 0.0000(6) C3 0.0127(7) 0.0158(8) 0.0151(7) 0.0003(6) 0.0026(6) -0.0019(6) C2 0.0158(8) 0.0172(8) 0.0205(8) 0.0007(6) 0.0076(6) -0.0015(7) C5 0.0291(10) 0.0307(10) 0.0202(9) -0.0036(7) 0.0077(7) -0.0022(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 N3 1.9651(14) . ? Cu1 N3 1.9651(14) 3_556 ? Cu1 N1 2.0363(14) . ? Cu1 N1 2.0363(14) 3_556 ? Cu1 O3 2.4863(13) . ? Cu1 O3 4.1669(13) 3_656 ? O2 C3 1.3241(19) . ? O2 C4 1.4510(19) . ? O3 C5 1.432(2) . ? O3 H3O 0.69(3) . ? O1 N1 1.2764(17) . ? N1 C1 1.320(2) . ? N3 C3 1.277(2) . ? N3 H3N 0.79(2) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? N2 C2 1.144(2) . ? C1 C2 1.428(2) . ? C1 C3 1.462(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? 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 N3 Cu1 N3 180.00(7) . 3_556 ? N3 Cu1 N1 81.44(6) . . ? N3 Cu1 N1 98.56(6) 3_556 . ? N3 Cu1 N1 98.56(6) . 3_556 ? N3 Cu1 N1 81.44(6) 3_556 3_556 ? N1 Cu1 N1 180.00(7) . 3_556 ? N3 Cu1 O3 88.54(5) . . ? N3 Cu1 O3 91.46(5) 3_556 . ? N1 Cu1 O3 90.86(5) . . ? N1 Cu1 O3 89.14(5) 3_556 . ? N3 Cu1 O3 41.07(5) . 3_656 ? N3 Cu1 O3 138.93(5) 3_556 3_656 ? N1 Cu1 O3 120.31(4) . 3_656 ? N1 Cu1 O3 59.69(4) 3_556 3_656 ? O3 Cu1 O3 76.27(4) . 3_656 ? C3 O2 C4 116.85(13) . . ? C5 O3 Cu1 115.53(11) . . ? C5 O3 H3O 111(2) . . ? Cu1 O3 H3O 103.4(19) . . ? O1 N1 C1 119.71(14) . . ? O1 N1 Cu1 128.45(11) . . ? C1 N1 Cu1 111.84(11) . . ? C3 N3 Cu1 114.09(11) . . ? C3 N3 H3N 118.9(16) . . ? Cu1 N3 H3N 126.8(16) . . ? O2 C4 H4A 109.5 . . ? O2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C1 C2 121.68(14) . . ? N1 C1 C3 114.62(14) . . ? C2 C1 C3 123.65(14) . . ? N3 C3 O2 128.50(15) . . ? N3 C3 C1 117.89(15) . . ? O2 C3 C1 113.61(14) . . ? N2 C2 C1 177.62(18) . . ? O3 C5 H5A 109.5 . . ? O3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N O3 0.79(2) 2.25(2) 2.9797(19) 154(2) 3_656 O3 H3O O1 0.69(3) 2.03(3) 2.7226(18) 173(3) 1_655 C4 H4B O1 0.98 2.38 3.350(2) 171.6 4_665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.390 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.057 #=END data_C:\AC261\AC261.CIF _database_code_depnum_ccdc_archive 'CCDC 648201' _audit_creation_method SHELXL-97 _chemical_name_systematic ; di(3-amino-3-methoxy-2nitrosoacrylonitrilate)dimethanolnickel(II) ; _chemical_name_common ;di(3-amino-3-methoxy- 2nitrosoacrylonitrilate)dimethanolnickel(ii) ; _chemical_melting_point ? _chemical_formula_moiety 'C10 H16 N6 Ni1 O6' _chemical_formula_sum 'C10 H16 N6 Ni1 O6' _chemical_formula_weight 375.00 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' Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 5.2198(1) _cell_length_b 15.9545(3) _cell_length_c 9.3351(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.222(1) _cell_angle_gamma 90.00 _cell_volume 769.43(3) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour purple _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 1.302 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.7627 _exptl_absorpt_correction_T_max 0.9030 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 Apex II CCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8666 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0132 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.55 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1754 _reflns_number_gt 1679 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART (Bruker)' _computing_cell_refinement 'Bruker SMART (Bruker)' _computing_data_reduction 'Bruker SAINT (Bruker)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1754 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0198 _refine_ls_R_factor_gt 0.0187 _refine_ls_wR_factor_ref 0.0469 _refine_ls_wR_factor_gt 0.0464 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 Ni1 Ni 0.0000 0.5000 0.5000 0.01183(7) Uani 1 2 d S . . O1 O 0.33784(16) 0.63392(5) 0.39021(9) 0.01797(18) Uani 1 1 d . . . N1 N 0.15912(18) 0.61601(6) 0.46662(10) 0.01353(19) Uani 1 1 d . . . C1 C 0.0535(2) 0.67681(7) 0.53403(12) 0.0143(2) Uani 1 1 d . . . O2 O -0.23459(16) 0.71221(5) 0.69448(9) 0.01855(18) Uani 1 1 d . . . N2 N 0.1897(2) 0.83076(7) 0.51110(13) 0.0243(2) Uani 1 1 d . . . C2 C 0.1289(2) 0.76258(7) 0.52331(13) 0.0166(2) Uani 1 1 d . . . O3 O -0.31139(17) 0.52212(5) 0.32802(9) 0.01705(17) Uani 1 1 d . . . N3 N -0.18799(19) 0.57146(6) 0.63123(11) 0.01469(19) Uani 1 1 d . . . C3 C -0.1375(2) 0.64958(7) 0.62545(12) 0.0137(2) Uani 1 1 d . . . H3N H -0.303(3) 0.5581(10) 0.6813(18) 0.028(4) Uiso 1 1 d . . . H3O H -0.418(4) 0.5552(12) 0.3498(19) 0.036(5) Uiso 1 1 d . . . C4 C -0.4079(2) 0.68937(8) 0.79563(14) 0.0206(2) Uani 1 1 d . . . H4A H -0.5533 0.6571 0.7453 0.031 Uiso 1 1 calc R . . H4B H -0.4735 0.7402 0.8367 0.031 Uiso 1 1 calc R . . H4C H -0.3145 0.6553 0.8735 0.031 Uiso 1 1 calc R . . C5 C -0.2586(3) 0.54609(9) 0.18592(14) 0.0253(3) Uani 1 1 d . . . H5A H -0.1253 0.5898 0.1952 0.038 Uiso 1 1 calc R . . H5B H -0.4173 0.5676 0.1290 0.038 Uiso 1 1 calc R . . H5C H -0.1975 0.4972 0.1371 0.038 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 Ni1 0.01265(11) 0.00802(11) 0.01589(11) -0.00052(7) 0.00565(7) -0.00004(7) O1 0.0167(4) 0.0153(4) 0.0242(4) 0.0031(3) 0.0109(3) 0.0001(3) N1 0.0123(4) 0.0125(4) 0.0162(5) 0.0013(4) 0.0035(3) 0.0002(3) C1 0.0147(5) 0.0108(5) 0.0173(5) -0.0002(4) 0.0024(4) -0.0002(4) O2 0.0212(4) 0.0135(4) 0.0225(4) -0.0035(3) 0.0084(3) 0.0023(3) N2 0.0271(5) 0.0150(5) 0.0321(6) -0.0009(4) 0.0082(5) -0.0022(4) C2 0.0158(5) 0.0158(6) 0.0188(6) -0.0015(4) 0.0039(4) 0.0012(4) O3 0.0173(4) 0.0144(4) 0.0206(4) 0.0011(3) 0.0067(3) 0.0025(3) N3 0.0147(4) 0.0127(5) 0.0180(5) -0.0003(4) 0.0069(4) 0.0001(4) C3 0.0127(5) 0.0139(5) 0.0144(5) -0.0017(4) 0.0015(4) 0.0023(4) C4 0.0199(6) 0.0214(6) 0.0220(6) -0.0045(5) 0.0084(5) 0.0011(5) C5 0.0264(6) 0.0306(7) 0.0200(6) 0.0055(5) 0.0069(5) 0.0044(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 Ni1 N3 2.0267(10) 3_566 ? Ni1 N3 2.0267(10) . ? Ni1 N1 2.0705(9) 3_566 ? Ni1 N1 2.0705(9) . ? Ni1 O3 2.1442(9) . ? Ni1 O3 2.1442(9) 3_566 ? O1 N1 1.2849(12) . ? N1 C1 1.3193(15) . ? C1 C2 1.4314(16) . ? C1 C3 1.4677(15) . ? O2 C3 1.3281(14) . ? O2 C4 1.4447(14) . ? N2 C2 1.1434(16) . ? O3 C5 1.4443(15) . ? O3 H3O 0.814(19) . ? N3 C3 1.2765(15) . ? N3 H3N 0.837(17) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? 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 N3 Ni1 N3 180.000(1) 3_566 . ? N3 Ni1 N1 80.06(4) 3_566 3_566 ? N3 Ni1 N1 99.94(4) . 3_566 ? N3 Ni1 N1 99.94(4) 3_566 . ? N3 Ni1 N1 80.06(4) . . ? N1 Ni1 N1 180.0 3_566 . ? N3 Ni1 O3 91.19(4) 3_566 . ? N3 Ni1 O3 88.81(4) . . ? N1 Ni1 O3 88.99(3) 3_566 . ? N1 Ni1 O3 91.01(3) . . ? N3 Ni1 O3 88.81(4) 3_566 3_566 ? N3 Ni1 O3 91.19(4) . 3_566 ? N1 Ni1 O3 91.01(3) 3_566 3_566 ? N1 Ni1 O3 88.99(3) . 3_566 ? O3 Ni1 O3 180.0 . 3_566 ? O1 N1 C1 119.18(10) . . ? O1 N1 Ni1 128.39(7) . . ? C1 N1 Ni1 112.42(7) . . ? N1 C1 C2 122.11(10) . . ? N1 C1 C3 115.14(10) . . ? C2 C1 C3 122.70(10) . . ? C3 O2 C4 116.45(9) . . ? N2 C2 C1 178.25(13) . . ? C5 O3 Ni1 120.50(7) . . ? C5 O3 H3O 106.5(13) . . ? Ni1 O3 H3O 113.1(13) . . ? C3 N3 Ni1 113.77(8) . . ? C3 N3 H3N 116.1(12) . . ? Ni1 N3 H3N 129.8(12) . . ? N3 C3 O2 128.22(11) . . ? N3 C3 C1 118.36(10) . . ? O2 C3 C1 113.41(10) . . ? O2 C4 H4A 109.5 . . ? O2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O3 C5 H5A 109.5 . . ? O3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? O3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H3N O3 0.837(17) 2.379(17) 3.0800(13) 141.8(15) 3_466 O3 H3O O1 0.814(19) 1.866(19) 2.6786(12) 176.9(18) 1_455 C4 H4B O1 0.98 2.32 3.2901(15) 169.4 4_476 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.387 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.043 #=END data_AC578.CIF _database_code_depnum_ccdc_archive 'CCDC 648202' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common AC578 _chemical_melting_point ? _chemical_formula_moiety 'C8 H12 Cu N6 O6' _chemical_formula_sum 'C8 H12 Cu N6 O6' _chemical_formula_weight 351.78 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' 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 5.1369(10) _cell_length_b 6.7710(14) _cell_length_c 10.113(2) _cell_angle_alpha 74.96(3) _cell_angle_beta 83.83(3) _cell_angle_gamma 79.17(3) _cell_volume 333.01(12) _cell_formula_units_Z 1 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.754 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 179 _exptl_absorpt_coefficient_mu 1.679 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7300 _exptl_absorpt_correction_T_max 0.9207 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(1) _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5983 _diffrn_reflns_av_R_equivalents 0.0435 _diffrn_reflns_av_sigmaI/netI 0.0309 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1527 _reflns_number_gt 1436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Hooft, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1527 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0287 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0627 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 0.01420(11) Uani 1 2 d S . . O3 O 0.3703(3) 0.3015(2) -0.11698(14) 0.0181(3) Uani 1 1 d . . . N3 N 0.2160(3) 0.4413(2) 0.15962(15) 0.0153(3) Uani 1 1 d . . . N1 N -0.0937(3) 0.2137(2) 0.10116(15) 0.0147(3) Uani 1 1 d . . . O1 O -0.2550(3) 0.11304(19) 0.06912(13) 0.0186(3) Uani 1 1 d . . . C3 C 0.2153(3) 0.2626(3) 0.24007(17) 0.0142(3) Uani 1 1 d . . . O2 O 0.3432(3) 0.17622(19) 0.35355(13) 0.0182(3) Uani 1 1 d . . . C4 C 0.4844(4) 0.3064(3) 0.40359(19) 0.0199(4) Uani 1 1 d . . . H4B H 0.6136 0.3626 0.3318 0.030 Uiso 1 1 calc R . . H4C H 0.5773 0.2236 0.4847 0.030 Uiso 1 1 calc R . . H4A H 0.3576 0.4208 0.4280 0.030 Uiso 1 1 calc R . . C1 C 0.0479(3) 0.1285(3) 0.20933(17) 0.0147(3) Uani 1 1 d . . . N2 N 0.0069(3) -0.2357(3) 0.35932(17) 0.0265(4) Uani 1 1 d . . . C2 C 0.0273(4) -0.0735(3) 0.29323(18) 0.0176(4) Uani 1 1 d . . . H1O H 0.476(6) 0.251(4) -0.065(3) 0.030(7) Uiso 1 1 d . . . H3N H 0.304(6) 0.510(4) 0.178(3) 0.035(7) Uiso 1 1 d . . . H2O H 0.315(5) 0.222(4) -0.136(3) 0.028(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 0.01699(17) 0.00951(16) 0.01651(17) 0.00011(11) -0.00598(11) -0.00510(11) O3 0.0175(7) 0.0154(6) 0.0236(7) -0.0041(5) -0.0070(5) -0.0054(5) N3 0.0174(8) 0.0117(7) 0.0179(7) -0.0026(6) -0.0056(6) -0.0043(6) N1 0.0132(7) 0.0129(7) 0.0195(7) -0.0058(6) -0.0012(5) -0.0034(5) O1 0.0176(6) 0.0140(6) 0.0268(7) -0.0045(5) -0.0070(5) -0.0064(5) C3 0.0137(8) 0.0147(8) 0.0142(8) -0.0043(6) -0.0027(6) -0.0007(6) O2 0.0237(7) 0.0142(6) 0.0177(6) -0.0018(5) -0.0106(5) -0.0034(5) C4 0.0218(9) 0.0218(9) 0.0192(9) -0.0061(7) -0.0088(7) -0.0053(7) C1 0.0156(8) 0.0130(8) 0.0158(8) -0.0032(6) -0.0024(6) -0.0024(6) N2 0.0314(10) 0.0181(8) 0.0281(9) -0.0005(7) -0.0020(7) -0.0067(7) C2 0.0178(9) 0.0167(9) 0.0199(9) -0.0057(7) -0.0031(7) -0.0039(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.9702(16) 2_565 ? Cu1 N3 1.9702(16) . ? Cu1 N1 2.0618(16) . ? Cu1 N1 2.0618(16) 2_565 ? Cu1 O3 2.4909(16) . ? O3 H1O 0.77(3) . ? O3 H2O 0.73(3) . ? N3 C3 1.271(2) . ? N3 H3N 0.77(3) . ? N1 O1 1.2813(18) . ? N1 C1 1.321(2) . ? C3 O2 1.327(2) . ? C3 C1 1.469(2) . ? O2 C4 1.453(2) . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C4 H4A 0.9800 . ? C1 C2 1.426(2) . ? N2 C2 1.145(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 N3 Cu1 N3 180.00(9) 2_565 . ? N3 Cu1 N1 99.08(6) 2_565 . ? N3 Cu1 N1 80.92(6) . . ? N3 Cu1 N1 80.92(6) 2_565 2_565 ? N3 Cu1 N1 99.08(6) . 2_565 ? N1 Cu1 N1 180.00(10) . 2_565 ? N3 Cu1 O3 90.72(6) 2_565 . ? N3 Cu1 O3 89.28(6) . . ? N1 Cu1 O3 85.34(6) . . ? N1 Cu1 O3 94.66(6) 2_565 . ? Cu1 O3 H1O 107(2) . . ? Cu1 O3 H2O 107(2) . . ? H1O O3 H2O 110(3) . . ? C3 N3 Cu1 114.63(12) . . ? C3 N3 H3N 116(2) . . ? Cu1 N3 H3N 129(2) . . ? O1 N1 C1 119.55(15) . . ? O1 N1 Cu1 128.93(11) . . ? C1 N1 Cu1 111.46(11) . . ? N3 C3 O2 129.08(16) . . ? N3 C3 C1 117.97(15) . . ? O2 C3 C1 112.94(15) . . ? C3 O2 C4 117.24(13) . . ? O2 C4 H4B 109.5 . . ? O2 C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? N1 C1 C2 122.23(16) . . ? N1 C1 C3 114.62(15) . . ? C2 C1 C3 123.07(15) . . ? N2 C2 C1 178.7(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H1O O1 0.77(3) 1.97(3) 2.736(2) 178(3) 1_655 N3 H3N O3 0.77(3) 2.23(3) 2.922(2) 149(3) 2_665 O3 H2O O1 0.73(3) 2.26(3) 2.8845(19) 144(3) 2 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.409 _refine_diff_density_min -0.582 _refine_diff_density_rms 0.071 #=END data_C:\AC693_2\AC693.CIF _database_code_depnum_ccdc_archive 'CCDC 648203' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'AC693 2' _chemical_melting_point ? _chemical_formula_moiety 'C8 H8 Cu1 N6 O4' _chemical_formula_sum 'C8 H8 Cu1 N6 O4' _chemical_formula_weight 315.74 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' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 11.6289(8) _cell_length_b 6.7788(8) _cell_length_c 7.3868(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.975(4) _cell_angle_gamma 90.00 _cell_volume 562.53(13) _cell_formula_units_Z 2 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.864 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 318 _exptl_absorpt_coefficient_mu 1.964 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8278 _exptl_absorpt_correction_T_max 0.9082 _exptl_absorpt_process_details SORTAV _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(1) _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 'Nonius KappaCCD' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3310 _diffrn_reflns_av_R_equivalents 0.0602 _diffrn_reflns_av_sigmaI/netI 0.0938 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1281 _reflns_number_gt 796 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Hooft, 1999)' _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1281 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1084 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_ref 0.0917 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.045 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.5000 0.5000 0.0191(2) Uani 1 2 d S . . O1 O 0.5093(2) 0.6563(4) 0.8757(4) 0.0225(7) Uani 1 1 d . . . N1 N 0.4453(3) 0.5840(5) 0.7255(4) 0.0193(8) Uani 1 1 d . . . C1 C 0.3302(3) 0.5402(5) 0.7043(5) 0.0169(9) Uani 1 1 d . . . O2 O 0.1520(2) 0.4550(4) 0.4916(4) 0.0227(7) Uani 1 1 d . . . N2 N 0.2198(3) 0.5646(5) 0.9627(5) 0.0282(9) Uani 1 1 d . . . C2 C 0.2704(4) 0.5586(6) 0.8498(6) 0.0203(10) Uani 1 1 d . . . N3 N 0.3292(3) 0.4651(5) 0.3940(5) 0.0186(8) Uani 1 1 d . . . C3 C 0.2685(3) 0.4813(6) 0.5142(5) 0.0164(8) Uani 1 1 d . . . C4 C 0.0813(4) 0.4086(7) 0.3047(6) 0.0283(11) Uani 1 1 d . . . H4A H 0.0898 0.5142 0.2185 0.043 Uiso 1 1 calc R . . H4B H -0.0026 0.3966 0.3056 0.043 Uiso 1 1 calc R . . H4C H 0.1086 0.2837 0.2636 0.043 Uiso 1 1 calc R . . H1 H 0.301(3) 0.442(5) 0.295(5) 0.000(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 0.0171(4) 0.0245(4) 0.0166(4) -0.0009(4) 0.0063(3) -0.0004(4) O1 0.0245(17) 0.0200(16) 0.0204(15) -0.0035(13) 0.0013(13) -0.0010(13) N1 0.025(2) 0.0143(17) 0.0179(18) 0.0032(15) 0.0051(16) 0.0014(15) C1 0.018(2) 0.019(3) 0.0152(19) 0.0007(17) 0.0063(16) -0.0002(17) O2 0.0146(15) 0.034(2) 0.0199(14) -0.0044(13) 0.0062(12) -0.0035(12) N2 0.027(2) 0.036(2) 0.0230(19) -0.0026(17) 0.0080(17) -0.0036(17) C2 0.021(2) 0.019(2) 0.020(2) 0.0006(18) 0.0040(19) -0.0027(17) N3 0.0171(17) 0.026(2) 0.0125(18) -0.0042(18) 0.0042(14) -0.0034(16) C3 0.017(2) 0.012(2) 0.0220(19) 0.0029(19) 0.0070(16) 0.003(2) C4 0.017(2) 0.040(3) 0.025(2) -0.010(2) 0.0016(19) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.952(3) 3_666 ? Cu1 N3 1.952(3) . ? Cu1 N1 2.013(3) 3_666 ? Cu1 N1 2.013(3) . ? Cu1 O1 2.517(3) 2_646 ? Cu1 O1 4.760(3) 1_554 ? O1 N1 1.265(4) . ? N1 C1 1.339(5) . ? C1 C2 1.428(5) . ? C1 C3 1.458(5) . ? O2 C3 1.334(4) . ? O2 C4 1.447(5) . ? N2 C2 1.140(5) . ? N3 C3 1.273(5) . ? N3 H1 0.74(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? 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 N3 Cu1 N3 180.0 3_666 . ? N3 Cu1 N1 81.93(14) 3_666 3_666 ? N3 Cu1 N1 98.07(14) . 3_666 ? N3 Cu1 N1 98.07(14) 3_666 . ? N3 Cu1 N1 81.93(14) . . ? N1 Cu1 N1 180.000(1) 3_666 . ? N3 Cu1 O1 95.80(12) 3_666 2_646 ? N3 Cu1 O1 84.20(12) . 2_646 ? N1 Cu1 O1 95.31(11) 3_666 2_646 ? N1 Cu1 O1 84.69(11) . 2_646 ? N3 Cu1 O1 94.94(10) 3_666 1_554 ? N3 Cu1 O1 85.06(10) . 1_554 ? N1 Cu1 O1 33.91(9) 3_666 1_554 ? N1 Cu1 O1 146.09(9) . 1_554 ? O1 Cu1 O1 124.98(7) 2_646 1_554 ? O1 N1 C1 122.1(3) . . ? O1 N1 Cu1 126.5(3) . . ? C1 N1 Cu1 111.1(3) . . ? N1 C1 C2 124.0(4) . . ? N1 C1 C3 113.6(3) . . ? C2 C1 C3 122.3(3) . . ? C3 O2 C4 117.2(3) . . ? N2 C2 C1 176.6(4) . . ? C3 N3 Cu1 113.5(3) . . ? C3 N3 H1 122(3) . . ? Cu1 N3 H1 124(3) . . ? N3 C3 O2 129.0(4) . . ? N3 C3 C1 118.2(3) . . ? O2 C3 C1 112.8(3) . . ? O2 C4 H4A 109.5 . . ? O2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N3 H1 N2 0.74(3) 2.53(4) 3.182(5) 148(4) 1_554 _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.806 _refine_diff_density_min -0.596 _refine_diff_density_rms 0.132 #=END OF CIF