# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Dr. John C. Plakatouras' _publ_contact_author_address ; Dr. John C. Plakatouras Department of Chemistry University of Ioannina 451 10 IOANNINA, Greece ; _publ_contact_author_email ; iplakatu@cc.uoi.gr ; loop_ _publ_author_name 'John Plakatouras' 'Luigi Castella' 'Nick Hadjliadis' 'George E. Kostakis' 'Nikolaos Kourkoumelis' 'Enrico Monzani' _publ_requested_journal ; Chemical Communications ; _publ_section_title ; Interpenetrated networks from a novel nanometer-sized pseudopeptidic ligand, bridging water, and transition metal ions with CdSO4 topology ; _publ_section_abstract ; The combination of a new pseudopeptidic ligand, transition metal ions, and bridging water molecules results in the formation of [M(?-TBG)(?-H2O)(H2O)2]?2H2O (M : Co, Cu and TBGH2 : Terephthaloyl-bisglycine); both compounds show rare two-fold interpenetrated three dimensional CdSO4-nets and reversible loss of coordinated and lattice water molecules. ; data_co _database_code_depnum_ccdc_archive 'CCDC 265226' _audit_creation_method SHELXL-97 _chemical_name_systematic ; mu!-terephthalamidodiacetate-mu!-aquo-diaquo-cobalt(II) dihydrate ; _chemical_name_common 'cobalt terephthaloyldiglycinate hydrate' _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 Co N2 O9, 2(H2 O)' _chemical_formula_sum 'C12 H20 Co N2 O11' _chemical_formula_weight 427.22 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' Co Co 0.3494 0.9721 '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 2/c' _symmetry_space_group_name_Hall '-P 2yc' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 16.012(5) _cell_length_b 6.907(5) _cell_length_c 7.971(5) _cell_angle_alpha 90.000 _cell_angle_beta 76.101(5) _cell_angle_gamma 90.000 _cell_volume 855.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6 _cell_measurement_theta_max 12 _exptl_crystal_description prism _exptl_crystal_colour 'light pink' _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 442 _exptl_absorpt_coefficient_mu 1.065 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.927 _exptl_absorpt_process_details 'North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351' _exptl_special_details ? _diffrn_ambient_temperature 295(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 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega-2theta scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 200 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2656 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 29.95 _reflns_number_total 2484 _reflns_number_gt 1626 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0849P)^2^+2.9695P] 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 2484 _refine_ls_number_parameters 139 _refine_ls_number_restraints 22 _refine_ls_R_factor_all 0.1166 _refine_ls_R_factor_gt 0.0723 _refine_ls_wR_factor_ref 0.2040 _refine_ls_wR_factor_gt 0.1824 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.086 _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 Co1 Co 0.0000 0.0000 0.5000 0.0170(2) Uani 1 2 d SD . . O5 O 0.0924(2) -0.1970(6) 0.5317(5) 0.0286(8) Uani 1 1 d D . . O1 O -0.0950(2) -0.1837(6) 0.6275(5) 0.0259(8) Uani 1 1 d . . . O2 O -0.1512(3) -0.2741(7) 0.4108(5) 0.0359(10) Uani 1 1 d . . . C2 C -0.2255(3) -0.3531(8) 0.7027(7) 0.0251(10) Uani 1 1 d . . . H2A H -0.2021 -0.4545 0.7621 0.030 Uiso 1 1 calc R . . H2B H -0.2487 -0.2537 0.7870 0.030 Uiso 1 1 calc R . . O3 O -0.3503(3) -0.1418(6) 0.5984(7) 0.0454(12) Uani 1 1 d . . . O4 O 0.0000 -0.1290(7) 0.2500 0.0190(9) Uani 1 2 d SD . . N1 N -0.2952(3) -0.4334(7) 0.6384(6) 0.0263(9) Uani 1 1 d . . . H1 H -0.2985 -0.5568 0.6275 0.032 Uiso 1 1 calc R . . C4 C -0.4282(3) -0.4172(9) 0.5448(7) 0.0249(11) Uani 1 1 d . . . C5 C -0.4386(4) -0.6186(9) 0.5408(9) 0.0371(15) Uani 1 1 d . . . H5 H -0.3977 -0.6993 0.5698 0.045 Uiso 1 1 calc R . . C3 C -0.3540(3) -0.3211(8) 0.5958(7) 0.0270(11) Uani 1 1 d . . . C1 C -0.1525(3) -0.2657(7) 0.5654(6) 0.0211(9) Uani 1 1 d . . . C6 C -0.4911(4) -0.3016(8) 0.5057(9) 0.0348(13) Uani 1 1 d . . . H6 H -0.4861 -0.1677 0.5108 0.042 Uiso 1 1 calc R . . O6 O 0.2577(3) -0.1614(6) 0.3231(6) 0.0338(9) Uani 1 1 d DU . . H41 H 0.0467(19) -0.189(7) 0.231(6) 0.020(15) Uiso 1 1 d D . . H52 H 0.096(6) -0.200(13) 0.640(6) 0.07(3) Uiso 1 1 d D . . H51 H 0.143(2) -0.194(9) 0.469(7) 0.019(15) Uiso 1 1 d D . . H61 H 0.250(5) -0.187(11) 0.222(6) 0.051(12) Uiso 1 1 d DU . . H62 H 0.281(5) -0.054(7) 0.315(10) 0.051(12) Uiso 1 1 d DU . . 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 Co1 0.0104(3) 0.0249(4) 0.0162(4) 0.0008(4) -0.0043(3) -0.0026(4) O5 0.0223(18) 0.039(2) 0.0258(19) 0.0005(17) -0.0072(15) 0.0070(16) O1 0.0170(15) 0.037(2) 0.0251(17) 0.0032(16) -0.0080(13) -0.0122(15) O2 0.035(2) 0.049(3) 0.0263(19) 0.0018(19) -0.0127(17) -0.0200(19) C2 0.023(2) 0.025(3) 0.029(2) 0.007(2) -0.0095(19) -0.008(2) O3 0.048(3) 0.023(2) 0.077(3) 0.005(2) -0.039(3) -0.0097(19) O4 0.014(2) 0.028(3) 0.016(2) 0.000 -0.0041(17) 0.000 N1 0.0176(19) 0.025(2) 0.037(2) 0.0029(19) -0.0099(17) -0.0069(16) C4 0.022(2) 0.027(3) 0.026(3) 0.000(2) -0.007(2) -0.009(2) C5 0.038(3) 0.030(3) 0.051(4) -0.002(3) -0.026(3) 0.000(2) C3 0.027(2) 0.026(3) 0.029(3) 0.002(2) -0.009(2) -0.010(2) C1 0.018(2) 0.023(2) 0.024(2) 0.0046(19) -0.0089(18) -0.0040(18) C6 0.031(3) 0.025(3) 0.053(3) 0.001(3) -0.018(3) -0.003(2) O6 0.032(2) 0.026(2) 0.044(2) -0.0012(18) -0.0103(18) 0.0013(17) _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 Co1 O1 2.053(4) . ? Co1 O5 2.070(4) . ? Co1 O4 2.183(2) . ? O5 H52 0.88(4) . ? O5 H51 0.84(3) . ? O1 C1 1.277(6) . ? O2 C1 1.229(6) . ? C2 N1 1.446(6) . ? C2 C1 1.521(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? O3 C3 1.240(7) . ? O4 Co1 2.183(2) 2 ? O4 H41 0.84(3) . ? N1 C3 1.326(7) . ? N1 H1 0.8600 . ? C4 C6 1.378(8) . ? C4 C5 1.402(9) . ? C4 C3 1.500(7) . ? C5 C6 1.382(8) 3_446 ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? O6 H61 0.87(4) . ? O6 H62 0.82(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Co1 O5 90.01(16) . 3_556 ? O1 Co1 O5 89.99(16) 3_556 3_556 ? O1 Co1 O5 89.99(16) . . ? O1 Co1 O5 90.01(16) 3_556 . ? O1 Co1 O4 87.87(14) . 3_556 ? O1 Co1 O4 92.13(14) 3_556 3_556 ? O5 Co1 O4 90.00(15) 3_556 3_556 ? O5 Co1 O4 90.00(15) . 3_556 ? O1 Co1 O4 92.13(14) . . ? O1 Co1 O4 87.87(14) 3_556 . ? O5 Co1 O4 90.00(15) 3_556 . ? O5 Co1 O4 90.00(15) . . ? Co1 O5 H52 111(6) . . ? Co1 O5 H51 122(4) . . ? H52 O5 H51 107(7) . . ? C1 O1 Co1 126.8(3) . . ? N1 C2 C1 115.0(4) . . ? N1 C2 H2A 108.5 . . ? C1 C2 H2A 108.5 . . ? N1 C2 H2B 108.5 . . ? C1 C2 H2B 108.5 . . ? H2A C2 H2B 107.5 . . ? Co1 O4 Co1 131.8(3) . 2 ? Co1 O4 H41 100(3) . . ? Co1 O4 H41 104(3) 2 . ? C3 N1 C2 121.5(5) . . ? C3 N1 H1 119.2 . . ? C2 N1 H1 119.2 . . ? C6 C4 C5 118.2(5) . . ? C6 C4 C3 118.3(5) . . ? C5 C4 C3 123.4(5) . . ? C6 C5 C4 120.7(6) 3_446 . ? C6 C5 H5 119.7 3_446 . ? C4 C5 H5 119.7 . . ? O3 C3 N1 122.7(5) . . ? O3 C3 C4 119.4(5) . . ? N1 C3 C4 117.9(5) . . ? O2 C1 O1 124.7(5) . . ? O2 C1 C2 121.9(4) . . ? O1 C1 C2 113.4(4) . . ? C4 C6 C5 121.0(5) . 3_446 ? C4 C6 H6 119.5 . . ? C5 C6 H6 119.5 3_446 . ? H61 O6 H62 106(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O5 Co1 O1 C1 63.4(4) 3_556 . . . ? O5 Co1 O1 C1 -116.6(4) . . . . ? O4 Co1 O1 C1 153.4(4) 3_556 . . . ? O4 Co1 O1 C1 -26.6(4) . . . . ? O1 Co1 O4 Co1 133.96(11) . . . 2 ? O1 Co1 O4 Co1 -46.04(11) 3_556 . . 2 ? O5 Co1 O4 Co1 43.95(12) 3_556 . . 2 ? O5 Co1 O4 Co1 -136.05(12) . . . 2 ? C1 C2 N1 C3 -77.6(6) . . . . ? C6 C4 C5 C6 1.8(12) . . . 3_446 ? C3 C4 C5 C6 179.3(6) . . . 3_446 ? C2 N1 C3 O3 4.4(9) . . . . ? C2 N1 C3 C4 -174.8(5) . . . . ? C6 C4 C3 O3 -1.3(9) . . . . ? C5 C4 C3 O3 -178.9(7) . . . . ? C6 C4 C3 N1 177.9(6) . . . . ? C5 C4 C3 N1 0.4(9) . . . . ? Co1 O1 C1 O2 13.2(8) . . . . ? Co1 O1 C1 C2 -166.1(3) . . . . ? N1 C2 C1 O2 -4.2(8) . . . . ? N1 C2 C1 O1 175.2(5) . . . . ? C5 C4 C6 C5 -1.8(12) . . . 3_446 ? C3 C4 C6 C5 -179.5(6) . . . 3_446 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 29.95 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.233 _refine_diff_density_min -0.546 _refine_diff_density_rms 0.140 data_cu _database_code_depnum_ccdc_archive 'CCDC 267859' _audit_creation_method SHELXL-97 _chemical_name_systematic ; mu!-terephthalamidodiacetate-mu!-aquo-diaquo-copper(II) dihydrate ; _chemical_name_common 'copper terephthaloyldiglycinate hydrate' _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 Cu N2 O9, 2(H2 O)' _chemical_formula_sum 'C12 H20 Cu N2 O11' _chemical_formula_weight 431.85 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 2/c' _symmetry_space_group_name_Hall '-P 2yc' _symmetry_Int_Tables_number 13 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 15.795(2) _cell_length_b 6.8256(14) _cell_length_c 8.1755(6) _cell_angle_alpha 90.00 _cell_angle_beta 77.004(7) _cell_angle_gamma 90.00 _cell_volume 858.8(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 7 _cell_measurement_theta_max 12 _exptl_crystal_description prism _exptl_crystal_colour 'pale green' _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 1.334 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.801 _exptl_absorpt_correction_T_max 0.872 _exptl_absorpt_process_details 'North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351' _exptl_special_details ? _diffrn_ambient_temperature 295(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 'Enraf-Nonius CAD4' _diffrn_measurement_method 'omega scans' _diffrn_standards_number 3 _diffrn_standards_interval_time 250 _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 2713 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0756 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.32 _diffrn_reflns_theta_max 29.97 _reflns_number_total 2504 _reflns_number_gt 1541 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SIR-97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'X-Seed (Barbour, 1999)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0377P)^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_number_reflns 2504 _refine_ls_number_parameters 144 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1010 _refine_ls_R_factor_gt 0.0471 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0797 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.049 _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 0.02120(14) Uani 1 2 d S . . O4 O 0.0000 0.3483(5) 0.2500 0.0276(7) Uani 1 2 d SD . . O1 O 0.09320(13) 0.3282(3) -0.1282(3) 0.0263(5) Uani 1 1 d . . . O5 O -0.08763(15) 0.3068(4) -0.0423(3) 0.0310(5) Uani 1 1 d D . . O6 O -0.25176(16) 0.3329(4) 0.1725(3) 0.0328(6) Uani 1 1 d D . . O2 O 0.15599(14) 0.2309(4) 0.0765(3) 0.0365(6) Uani 1 1 d . . . C3 C 0.3561(2) 0.1874(5) -0.1033(4) 0.0297(7) Uani 1 1 d . . . C4 C 0.4288(2) 0.0847(6) -0.0490(4) 0.0243(7) Uani 1 1 d . . . O3 O 0.35264(17) 0.3672(4) -0.1071(4) 0.0451(7) Uani 1 1 d . . . N1 N 0.29604(16) 0.0743(4) -0.1493(3) 0.0283(6) Uani 1 1 d . . . H1 H 0.3003 -0.0510 -0.1432 0.034 Uiso 1 1 calc R . . C1 C 0.15313(18) 0.2442(5) -0.0720(4) 0.0236(6) Uani 1 1 d . . . C2 C 0.22457(19) 0.1571(5) -0.2087(4) 0.0276(7) Uani 1 1 d . . . H2A H 0.1995 0.0557 -0.2663 0.033 Uiso 1 1 calc R . . H2B H 0.2469 0.2586 -0.2900 0.033 Uiso 1 1 calc R . . C5 C 0.4913(3) 0.1984(5) -0.0034(6) 0.0403(9) Uani 1 1 d . . . H5 H 0.4862 0.3341 -0.0055 0.048 Uiso 1 1 calc R . . C6 C 0.4383(2) -0.1158(6) -0.0456(6) 0.0391(10) Uani 1 1 d . . . H6 H 0.3970 -0.1963 -0.0765 0.047 Uiso 1 1 calc R . . H61 H -0.242(3) 0.328(7) 0.262(4) 0.054(14) Uiso 1 1 d D . . H51 H -0.091(3) 0.328(6) -0.141(4) 0.053(13) Uiso 1 1 d D . . H41 H 0.046(2) 0.285(7) 0.219(7) 0.10(2) Uiso 1 1 d D . . H52 H -0.138(2) 0.313(7) 0.018(5) 0.058(14) Uiso 1 1 d D . . H62 H -0.286(3) 0.418(6) 0.164(6) 0.073(17) Uiso 1 1 d 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 0.0153(2) 0.0291(3) 0.0209(2) -0.0017(3) -0.00737(16) 0.0031(3) O4 0.0235(16) 0.034(2) 0.0259(16) 0.000 -0.0078(13) 0.000 O1 0.0203(10) 0.0359(13) 0.0256(11) -0.0044(10) -0.0110(8) 0.0094(9) O5 0.0239(11) 0.0442(15) 0.0268(12) 0.0011(12) -0.0098(10) -0.0039(11) O6 0.0322(13) 0.0318(14) 0.0376(15) 0.0003(12) -0.0149(11) 0.0026(11) O2 0.0303(12) 0.0563(17) 0.0255(12) -0.0003(12) -0.0119(10) 0.0151(12) C3 0.0258(15) 0.0333(19) 0.0321(17) -0.0041(15) -0.0109(13) 0.0070(14) C4 0.0169(15) 0.0288(17) 0.0275(17) -0.0009(14) -0.0057(13) 0.0021(13) O3 0.0410(14) 0.0255(14) 0.079(2) -0.0015(13) -0.0345(14) 0.0075(11) N1 0.0231(12) 0.0278(14) 0.0368(15) -0.0039(12) -0.0128(11) 0.0093(11) C1 0.0185(13) 0.0255(17) 0.0284(15) -0.0011(14) -0.0088(12) 0.0008(12) C2 0.0226(14) 0.0331(18) 0.0299(16) -0.0048(15) -0.0117(13) 0.0069(14) C5 0.036(2) 0.0230(15) 0.071(2) 0.001(2) -0.0294(18) 0.0051(17) C6 0.034(2) 0.027(2) 0.065(3) 0.0001(19) -0.030(2) 0.0000(16) _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 1.986(2) . ? Cu1 O5 1.998(2) . ? Cu1 O4 2.2911(16) . ? O4 H41 0.83(3) . ? O1 C1 1.277(3) . ? O5 H51 0.83(3) . ? O5 H52 0.84(3) . ? O6 H61 0.78(3) . ? O6 H62 0.81(3) . ? O2 C1 1.228(3) . ? C3 O3 1.229(4) . ? C3 N1 1.340(4) . ? C3 C4 1.495(4) . ? C4 C5 1.372(5) . ? C4 C6 1.378(5) . ? N1 C2 1.441(4) . ? N1 H1 0.8600 . ? C1 C2 1.520(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C5 H5 0.9300 . ? C6 C5 1.384(5) 3_655 ? C6 H6 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 O5 88.80(10) . . ? O1 Cu1 O5 91.20(10) 3_565 . ? O1 Cu1 O5 91.20(10) . 3_565 ? O1 Cu1 O5 88.80(10) 3_565 3_565 ? O1 Cu1 O4 93.17(8) . . ? O1 Cu1 O4 86.83(8) 3_565 . ? O5 Cu1 O4 89.73(9) . . ? O5 Cu1 O4 90.27(9) 3_565 . ? O1 Cu1 O4 86.83(8) . 3_565 ? O1 Cu1 O4 93.17(8) 3_565 3_565 ? O5 Cu1 O4 90.27(9) . 3_565 ? Cu1 O4 Cu1 126.28(16) 2 . ? Cu1 O4 H41 109(4) 2 . ? Cu1 O4 H41 98(4) . . ? C1 O1 Cu1 126.6(2) . . ? Cu1 O5 H51 105(3) . . ? Cu1 O5 H52 118(3) . . ? H51 O5 H52 107(4) . . ? H61 O6 H62 113(5) . . ? O3 C3 N1 122.0(3) . . ? O3 C3 C4 121.1(3) . . ? N1 C3 C4 116.9(3) . . ? C5 C4 C6 117.9(3) . . ? C5 C4 C3 117.6(3) . . ? C6 C4 C3 124.5(3) . . ? C3 N1 C2 121.7(3) . . ? C3 N1 H1 119.1 . . ? C2 N1 H1 119.1 . . ? O2 C1 O1 125.7(3) . . ? O2 C1 C2 120.8(3) . . ? O1 C1 C2 113.5(3) . . ? N1 C2 C1 114.4(3) . . ? N1 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N1 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C4 C5 C6 121.5(3) . 3_655 ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 3_655 . ? C4 C6 C5 120.6(4) . 3_655 ? C4 C6 H6 119.7 . . ? C5 C6 H6 119.7 3_655 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O4 Cu1 133.68(6) . . . 2 ? O1 Cu1 O4 Cu1 -46.32(6) 3_565 . . 2 ? O5 Cu1 O4 Cu1 -137.53(7) . . . 2 ? O5 Cu1 O4 Cu1 42.47(7) 3_565 . . 2 ? O5 Cu1 O1 C1 -118.0(3) . . . . ? O5 Cu1 O1 C1 62.0(3) 3_565 . . . ? O4 Cu1 O1 C1 -28.3(3) . . . . ? O4 Cu1 O1 C1 151.7(3) 3_565 . . . ? O3 C3 C4 C5 0.1(5) . . . . ? N1 C3 C4 C5 179.3(4) . . . . ? O3 C3 C4 C6 -178.2(4) . . . . ? N1 C3 C4 C6 0.9(6) . . . . ? O3 C3 N1 C2 1.0(5) . . . . ? C4 C3 N1 C2 -178.1(3) . . . . ? Cu1 O1 C1 O2 11.7(5) . . . . ? Cu1 O1 C1 C2 -168.3(2) . . . . ? C3 N1 C2 C1 -75.5(4) . . . . ? O2 C1 C2 N1 -4.4(5) . . . . ? O1 C1 C2 N1 175.7(3) . . . . ? C6 C4 C5 C6 -0.4(8) . . . 3_655 ? C3 C4 C5 C6 -178.8(4) . . . 3_655 ? C5 C4 C6 C5 0.4(8) . . . 3_655 ? C3 C4 C6 C5 178.7(4) . . . 3_655 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 29.97 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.489 _refine_diff_density_min -0.393 _refine_diff_density_rms 0.093