Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Batten, Stuart' _publ_contact_author_address ; Clayton Victoria Australia 3800 ; _publ_contact_author_email stuart.batten@sci.monash.edu.au loop_ _publ_author_name A.Chesman D.Turner G.Deacon S.Batten # Attachment '- 2.CIF' data_AC602B.CIF _database_code_depnum_ccdc_archive 'CCDC 720116' #TrackingRef '- 2.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(4,4'-bipyridine)bis(carbamoylcyanonitrosomethanido)copper(II)] ; _chemical_name_common ;((4,4'- bipyridine)bis(carbamoylcyanonitrosomethanido)copper(ii)) ; _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 Cu N8 O4' _chemical_formula_sum 'C16 H12 Cu N8 O4' _chemical_formula_weight 443.88 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 tetragonal _symmetry_space_group_name_H-M P43212 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y+1/2, x+1/2, z+3/4' '-x, -y, z+1/2' 'y+1/2, -x+1/2, z+1/4' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 7.8075(3) _cell_length_b 7.8075(3) _cell_length_c 29.146(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1776.62(19) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 6715 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.659 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 900 _exptl_absorpt_coefficient_mu 1.274 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8418 _exptl_absorpt_correction_T_max 0.8621 _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 6715 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0517 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 27.49 _reflns_number_total 2041 _reflns_number_gt 1826 _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 SHELXL _refine_ls_extinction_coef none _refine_ls_extinction_expression ? _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 2041 _refine_ls_number_parameters 142 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.17765(4) 0.17765(4) 0.0000 0.01256(13) Uani 1 2 d S . . O2 O 0.5080(3) 0.1631(3) 0.19238(6) 0.0181(4) Uani 1 1 d . . . N1 N 0.3510(3) 0.1543(3) 0.08021(8) 0.0204(6) Uani 1 1 d . . . C1 C 0.4048(4) 0.0894(4) 0.11925(10) 0.0203(8) Uani 1 1 d . . . H1N H 0.501(6) 0.483(6) 0.1615(15) 0.077(14) Uiso 1 1 d . . . O1 O 0.2949(3) 0.0477(3) 0.04946(6) 0.0207(5) Uani 1 1 d . . . N2 N 0.4156(6) -0.2306(5) 0.13776(10) 0.0548(11) Uani 1 1 d . . . C2 C 0.4101(5) -0.0885(5) 0.12989(10) 0.0300(9) Uani 1 1 d . . . H2N H 0.415(5) 0.394(5) 0.1138(13) 0.050(12) Uiso 1 1 d . . . N3 N 0.4599(4) 0.3783(4) 0.14147(10) 0.0288(7) Uani 1 1 d . . . C3 C 0.4634(4) 0.2134(4) 0.15425(10) 0.0202(7) Uani 1 1 d . . . N4 N 0.3581(3) 0.3581(3) 0.0000 0.0125(7) Uani 1 2 d S . . C4 C 0.3377(4) 0.5046(4) 0.02314(9) 0.0161(6) Uani 1 1 d . . . H4 H 0.2349 0.5207 0.0400 0.019 Uiso 1 1 calc R . . N5 N 0.9954(3) 0.9954(3) 0.0000 0.0141(6) Uani 1 2 d S . . C5 C 0.4577(4) 0.6327(4) 0.02374(10) 0.0165(7) Uani 1 1 d . . . H5 H 0.4366 0.7356 0.0402 0.020 Uiso 1 1 calc R . . C6 C 0.6106(3) 0.6106(3) 0.0000 0.0133(8) Uani 1 2 d S . . C7 C 0.7453(3) 0.7453(3) 0.0000 0.0140(8) Uani 1 2 d S . . C8 C 0.7022(4) 0.9163(3) 0.00456(9) 0.0164(6) Uani 1 1 d . . . H8 H 0.5859 0.9497 0.0080 0.020 Uiso 1 1 calc R . . C9 C 0.8301(4) 1.0370(3) 0.00400(10) 0.0174(6) Uani 1 1 d . . . H9 H 0.7999 1.1545 0.0065 0.021 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 0.01297(16) 0.01297(16) 0.0117(2) 0.00213(15) -0.00213(15) -0.0043(2) O2 0.0209(11) 0.0189(12) 0.0143(9) 0.0017(9) -0.0050(8) 0.0062(9) N1 0.0186(14) 0.0211(15) 0.0216(12) -0.0011(12) 0.0018(11) 0.0002(12) C1 0.0223(19) 0.0223(19) 0.0164(14) 0.0002(14) -0.0016(14) -0.0004(14) O1 0.0231(13) 0.0218(12) 0.0172(9) 0.0002(9) -0.0026(9) -0.0023(9) N2 0.108(3) 0.026(2) 0.0299(18) 0.0000(15) -0.004(2) 0.0014(19) C2 0.049(3) 0.027(2) 0.0143(15) -0.0059(16) -0.0028(16) -0.0023(18) N3 0.045(2) 0.0191(16) 0.0226(15) 0.0051(12) -0.0098(14) 0.0027(13) C3 0.0179(17) 0.0203(18) 0.0223(15) -0.0005(13) 0.0000(13) 0.0042(13) N4 0.0122(10) 0.0122(10) 0.0132(14) 0.0019(11) -0.0019(11) -0.0043(12) C4 0.0134(15) 0.0188(15) 0.0160(13) 0.0018(12) 0.0003(13) -0.0051(14) N5 0.0144(9) 0.0144(9) 0.0135(14) 0.0004(10) -0.0004(10) -0.0022(12) C5 0.0163(16) 0.0135(16) 0.0196(15) -0.0033(12) 0.0033(13) -0.0010(11) C6 0.0131(12) 0.0131(12) 0.0137(17) -0.0003(14) 0.0003(14) -0.0030(15) C7 0.0149(13) 0.0149(13) 0.0123(17) 0.0004(14) -0.0004(14) -0.0066(15) C8 0.0129(15) 0.0163(14) 0.0200(14) -0.0018(13) 0.0024(14) -0.0004(11) C9 0.0170(14) 0.0130(13) 0.0221(14) 0.0001(13) -0.0010(16) 0.0008(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 1.9862(19) 7 ? Cu1 O1 1.9862(19) . ? Cu1 N4 1.992(3) . ? Cu1 N5 2.012(3) 1_445 ? O2 C3 1.229(3) . ? N1 O1 1.299(3) . ? N1 C1 1.314(4) . ? C1 C2 1.424(4) . ? C1 C3 1.479(4) . ? N2 C2 1.134(4) . ? N3 C3 1.341(4) . ? N3 H1N 1.05(5) . ? N3 H2N 0.89(4) . ? N4 C4 1.338(3) 7 ? N4 C4 1.338(3) . ? C4 C5 1.370(4) . ? C4 H4 0.9500 . ? N5 C9 1.336(3) 7 ? N5 C9 1.336(3) . ? N5 Cu1 2.012(3) 1_665 ? C5 C6 1.391(3) . ? C5 H5 0.9500 . ? C6 C5 1.391(3) 7 ? C6 C7 1.487(5) . ? C7 C8 1.383(3) . ? C7 C8 1.383(3) 7 ? C8 C9 1.374(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? 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 175.95(13) 7 . ? O1 Cu1 N4 92.03(7) 7 . ? O1 Cu1 N4 92.03(7) . . ? O1 Cu1 N5 87.97(7) 7 1_445 ? O1 Cu1 N5 87.97(7) . 1_445 ? N4 Cu1 N5 180.00(3) . 1_445 ? O1 N1 C1 117.3(3) . . ? N1 C1 C2 125.0(3) . . ? N1 C1 C3 116.4(3) . . ? C2 C1 C3 118.6(3) . . ? N1 O1 Cu1 109.19(17) . . ? N2 C2 C1 179.0(4) . . ? C3 N3 H1N 126(2) . . ? C3 N3 H2N 113(3) . . ? H1N N3 H2N 121(4) . . ? O2 C3 N3 124.3(3) . . ? O2 C3 C1 120.2(3) . . ? N3 C3 C1 115.5(3) . . ? C4 N4 C4 117.2(3) 7 . ? C4 N4 Cu1 121.39(17) 7 . ? C4 N4 Cu1 121.39(17) . . ? N4 C4 C5 123.3(3) . . ? N4 C4 H4 118.3 . . ? C5 C4 H4 118.3 . . ? C9 N5 C9 118.5(3) 7 . ? C9 N5 Cu1 120.74(17) 7 1_665 ? C9 N5 Cu1 120.74(17) . 1_665 ? C4 C5 C6 119.3(3) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C5 C6 C5 117.5(4) 7 . ? C5 C6 C7 121.27(18) 7 . ? C5 C6 C7 121.27(18) . . ? C8 C7 C8 118.6(3) . 7 ? C8 C7 C6 120.72(17) . . ? C8 C7 C6 120.72(17) 7 . ? C9 C8 C7 119.0(3) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? N5 C9 C8 122.4(3) . . ? N5 C9 H9 118.8 . . ? C8 C9 H9 118.8 . . ? 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 H1N N2 1.05(5) 2.43(5) 3.075(5) 118(3) 1_565 N3 H1N O1 1.05(5) 2.57(5) 3.184(4) 116(3) 5 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.514 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.071 data_AC3325.CIF _database_code_depnum_ccdc_archive 'CCDC 720117' _audit_creation_method SHELXL-97 _chemical_name_systematic ; [(4,4'-bipyridine)bis(carbamoylcyanonitrosomethanide)copper (II)].tetramethanol ; _chemical_name_common ;((4,4'-bipyridine)bis(carbamoylcyanonitrosomethanide)copper (ii)).tetramethanol ; _chemical_melting_point ? _chemical_formula_moiety 'C16 H12 Cu N8 O4, 4(C H4 O)' _chemical_formula_sum 'C20 H28 Cu N8 O8' _chemical_formula_weight 572.04 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 orthorhombic _symmetry_space_group_name_H-M Pbcn 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 11.4025(3) _cell_length_b 11.0978(3) _cell_length_c 20.1842(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2554.16(12) _cell_formula_units_Z 4 _cell_measurement_temperature 123(1) _cell_measurement_reflns_used 11636 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 27.50 _exptl_crystal_description plate _exptl_crystal_colour magenta _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 0.915 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.8674 _exptl_absorpt_correction_T_max 0.9140 _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 11636 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 27.50 _reflns_number_total 2903 _reflns_number_gt 2596 _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 SHELXL _refine_ls_extinction_coef none _refine_ls_extinction_expression ? _refine_ls_number_reflns 2903 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0324 _refine_ls_R_factor_gt 0.0282 _refine_ls_wR_factor_ref 0.0732 _refine_ls_wR_factor_gt 0.0706 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 0.5000 0.13433(2) 0.7500 0.00816(9) Uani 1 2 d S . . O1 O 0.68731(10) 0.12399(10) 0.65332(5) 0.0147(2) Uani 1 1 d . . . N1 N 0.57578(11) 0.13632(10) 0.65926(6) 0.0101(2) Uani 1 1 d . . . C1 C 0.50895(13) 0.14957(13) 0.60642(8) 0.0119(3) Uani 1 1 d . . . H1N H 0.340(2) 0.209(2) 0.5309(11) 0.029(6) Uiso 1 1 d . . . H1O H 0.805(2) 0.189(2) 0.5852(11) 0.032(6) Uiso 1 1 d . . . O2 O 0.34232(10) 0.14357(9) 0.67533(5) 0.0123(2) Uani 1 1 d . . . N2 N 0.60110(14) 0.13971(15) 0.48994(7) 0.0268(4) Uani 1 1 d . . . C2 C 0.55963(14) 0.14602(15) 0.54146(8) 0.0161(3) Uani 1 1 d . . . H2N H 0.240(2) 0.1906(19) 0.5728(10) 0.029(6) Uiso 1 1 d . . . H2O H 1.010(2) 0.138(2) 0.5789(13) 0.035(7) Uiso 1 1 d . . . O3 O 0.85553(11) 0.22721(11) 0.57079(6) 0.0193(3) Uani 1 1 d . . . N3 N 0.31322(13) 0.18951(14) 0.56744(7) 0.0175(3) Uani 1 1 d . . . C3 C 0.38089(14) 0.16111(13) 0.61844(7) 0.0115(3) Uani 1 1 d . . . O4 O 1.07598(14) 0.11014(13) 0.58602(9) 0.0366(4) Uani 1 1 d . . . N4 N 0.5000 0.31665(16) 0.7500 0.0110(3) Uani 1 2 d S . . C4 C 0.40045(14) 0.37862(13) 0.76058(7) 0.0122(3) Uani 1 1 d . . . H4 H 0.3300 0.3352 0.7683 0.015 Uiso 1 1 calc R . . N5 N 0.5000 0.95222(16) 0.7500 0.0104(3) Uani 1 2 d S . . C5 C 0.39657(14) 0.50348(14) 0.76065(7) 0.0130(3) Uani 1 1 d . . . H5 H 0.3247 0.5447 0.7678 0.016 Uiso 1 1 calc R . . C6 C 0.5000 0.56744(19) 0.7500 0.0117(4) Uani 1 2 d S . . C7 C 0.5000 0.70119(19) 0.7500 0.0113(4) Uani 1 2 d S . . C8 C 0.40884(13) 0.76550(13) 0.72073(7) 0.0126(3) Uani 1 1 d . . . H8 H 0.3448 0.7244 0.7008 0.015 Uiso 1 1 calc R . . C9 C 0.41279(13) 0.89025(13) 0.72110(7) 0.0122(3) Uani 1 1 d . . . H9 H 0.3514 0.9337 0.7001 0.015 Uiso 1 1 calc R . . C10 C 0.84472(18) 0.34365(16) 0.60050(9) 0.0249(4) Uani 1 1 d . . . H10A H 0.8381 0.3349 0.6487 0.037 Uiso 1 1 calc R . . H10B H 0.7745 0.3839 0.5833 0.037 Uiso 1 1 calc R . . H10C H 0.9142 0.3920 0.5899 0.037 Uiso 1 1 calc R . . C11 C 1.0757(2) -0.01614(18) 0.58034(10) 0.0367(5) Uani 1 1 d . . . H11A H 1.1464 -0.0489 0.6013 0.055 Uiso 1 1 calc R . . H11B H 1.0747 -0.0387 0.5334 0.055 Uiso 1 1 calc R . . H11C H 1.0060 -0.0488 0.6023 0.055 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 0.00756(14) 0.00709(13) 0.00982(13) 0.000 0.00072(9) 0.000 O1 0.0057(5) 0.0206(6) 0.0177(5) 0.0019(4) 0.0011(4) 0.0015(4) N1 0.0078(6) 0.0084(6) 0.0140(6) 0.0005(4) 0.0006(5) 0.0008(5) C1 0.0102(8) 0.0133(7) 0.0123(7) 0.0013(5) 0.0009(5) 0.0005(6) O2 0.0096(5) 0.0150(5) 0.0124(5) 0.0005(4) 0.0005(4) 0.0012(4) N2 0.0182(8) 0.0448(10) 0.0175(7) 0.0042(6) 0.0021(6) 0.0024(7) C2 0.0086(8) 0.0227(8) 0.0170(7) 0.0035(6) -0.0018(6) -0.0003(6) O3 0.0145(6) 0.0227(6) 0.0208(6) 0.0003(5) 0.0027(5) -0.0038(5) N3 0.0102(7) 0.0290(8) 0.0134(6) 0.0035(6) -0.0010(5) 0.0028(6) C3 0.0104(7) 0.0088(6) 0.0154(7) -0.0007(5) -0.0010(6) 0.0000(5) O4 0.0179(7) 0.0223(7) 0.0696(11) -0.0018(7) -0.0035(7) 0.0013(6) N4 0.0106(9) 0.0097(8) 0.0127(8) 0.000 0.0000(6) 0.000 C4 0.0087(8) 0.0124(7) 0.0157(7) 0.0002(5) 0.0008(5) -0.0013(6) N5 0.0101(9) 0.0095(8) 0.0115(8) 0.000 0.0009(6) 0.000 C5 0.0094(7) 0.0119(7) 0.0179(7) -0.0008(6) 0.0016(6) 0.0013(6) C6 0.0125(11) 0.0101(9) 0.0126(9) 0.000 -0.0008(8) 0.000 C7 0.0100(10) 0.0108(9) 0.0131(9) 0.000 0.0022(7) 0.000 C8 0.0087(7) 0.0116(7) 0.0175(7) -0.0017(6) -0.0016(6) -0.0019(6) C9 0.0094(7) 0.0122(7) 0.0151(7) 0.0009(6) -0.0015(6) 0.0008(6) C10 0.0294(10) 0.0249(9) 0.0204(8) -0.0024(7) 0.0034(7) -0.0044(8) C11 0.0556(15) 0.0239(9) 0.0306(10) -0.0021(8) -0.0022(10) 0.0017(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 N5 2.0211(18) 1_545 ? Cu1 N4 2.0233(18) . ? Cu1 N1 2.0253(12) 4_656 ? Cu1 N1 2.0253(13) . ? Cu1 O2 2.3483(11) 4_656 ? Cu1 O2 2.3483(11) . ? O1 N1 1.2846(17) . ? N1 C1 1.319(2) . ? C1 C2 1.433(2) . ? C1 C3 1.486(2) . ? O2 C3 1.2449(18) . ? N2 C2 1.145(2) . ? O3 C10 1.430(2) . ? O3 H1O 0.77(2) . ? N3 C3 1.325(2) . ? N3 H1N 0.83(2) . ? N3 H2N 0.85(2) . ? O4 C11 1.406(2) . ? O4 H2O 0.83(3) . ? N4 C4 1.3443(18) . ? N4 C4 1.3443(18) 4_656 ? C4 C5 1.386(2) . ? C4 H4 0.9500 . ? N5 C9 1.3424(17) . ? N5 C9 1.3424(17) 4_656 ? N5 Cu1 2.0211(18) 1_565 ? C5 C6 1.3932(19) . ? C5 H5 0.9500 . ? C6 C5 1.3932(19) 4_656 ? C6 C7 1.484(3) . ? C7 C8 1.3924(18) 4_656 ? C7 C8 1.3924(18) . ? C8 C9 1.385(2) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 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 N5 Cu1 N4 180.000(1) 1_545 . ? N5 Cu1 N1 90.62(3) 1_545 4_656 ? N4 Cu1 N1 89.38(3) . 4_656 ? N5 Cu1 N1 90.62(3) 1_545 . ? N4 Cu1 N1 89.38(3) . . ? N1 Cu1 N1 178.75(7) 4_656 . ? N5 Cu1 O2 92.50(3) 1_545 4_656 ? N4 Cu1 O2 87.50(3) . 4_656 ? N1 Cu1 O2 75.28(4) 4_656 4_656 ? N1 Cu1 O2 104.67(4) . 4_656 ? N5 Cu1 O2 92.50(3) 1_545 . ? N4 Cu1 O2 87.50(3) . . ? N1 Cu1 O2 104.67(4) 4_656 . ? N1 Cu1 O2 75.28(4) . . ? O2 Cu1 O2 174.99(5) 4_656 . ? O1 N1 C1 120.55(13) . . ? O1 N1 Cu1 120.37(10) . . ? C1 N1 Cu1 119.07(10) . . ? N1 C1 C2 120.24(14) . . ? N1 C1 C3 116.45(13) . . ? C2 C1 C3 123.23(14) . . ? C3 O2 Cu1 109.16(10) . . ? N2 C2 C1 177.95(18) . . ? C10 O3 H1O 106.1(17) . . ? C3 N3 H1N 122.5(16) . . ? C3 N3 H2N 118.8(15) . . ? H1N N3 H2N 119(2) . . ? O2 C3 N3 123.24(15) . . ? O2 C3 C1 118.97(14) . . ? N3 C3 C1 117.78(14) . . ? C11 O4 H2O 110.7(16) . . ? C4 N4 C4 118.46(18) . 4_656 ? C4 N4 Cu1 120.77(9) . . ? C4 N4 Cu1 120.77(9) 4_656 . ? N4 C4 C5 122.58(15) . . ? N4 C4 H4 118.7 . . ? C5 C4 H4 118.7 . . ? C9 N5 C9 118.37(18) . 4_656 ? C9 N5 Cu1 120.81(9) . 1_565 ? C9 N5 Cu1 120.81(9) 4_656 1_565 ? C4 C5 C6 118.82(15) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? C5 C6 C5 118.7(2) . 4_656 ? C5 C6 C7 120.63(10) . . ? C5 C6 C7 120.63(10) 4_656 . ? C8 C7 C8 118.33(19) 4_656 . ? C8 C7 C6 120.84(10) 4_656 . ? C8 C7 C6 120.84(10) . . ? C9 C8 C7 119.06(14) . . ? C9 C8 H8 120.5 . . ? C7 C8 H8 120.5 . . ? N5 C9 C8 122.57(14) . . ? N5 C9 H9 118.7 . . ? C8 C9 H9 118.7 . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O4 C11 H11A 109.5 . . ? O4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 H1N O3 0.83(2) 2.18(2) 2.9785(18) 163(2) 3_456 N3 H2N O4 0.85(2) 2.09(2) 2.869(2) 154(2) 1_455 O3 H1O O1 0.77(2) 2.05(2) 2.7868(17) 159(2) . O4 H2O O3 0.83(3) 2.02(3) 2.846(2) 171(2) . _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.413 _refine_diff_density_min -0.313 _refine_diff_density_rms 0.057