# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'ProfD Hong-Cai Zhou' _publ_contact_author_address ; Chemistry and Biochemistry Miami University Oxford Ohio USA ; _publ_contact_author_email ZHOUH@MUOHIO.EDU _publ_section_title ; Temperature-dependent supramolecular stereoisomerism in porous copper coordination networks based on a designed carboxylate ligand ; loop_ _publ_author_name 'Hong-Cai Zhou.' 'Yanxiong Ke.' 'Betty A. Ooro' 'Tracy M. Peterson' 'Daofeng Sun.' data_xamd324s _database_code_depnum_ccdc_archive 'CCDC 269580' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common none _chemical_melting_point 'not measured' _chemical_formula_moiety 'Cu2 (C34 H20 N2 O8) 2(H2 O)' _chemical_formula_sum 'C34 H24 Cu2 N2 O10' _chemical_formula_weight 747.63 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 Cccm loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x, y, -z+1/2' 'x, -y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x, y, -z' 'x, -y, z-1/2' '-x, y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' '-x+1/2, y+1/2, z-1/2' _cell_length_a 15.2563(12) _cell_length_b 28.288(2) _cell_length_c 23.5937(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10182.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3468 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.92 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 0.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.437 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.839 _exptl_absorpt_correction_T_max 0.854 _exptl_absorpt_process_details sadas _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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_% none _diffrn_reflns_number 29155 _diffrn_reflns_av_R_equivalents 0.0791 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 33 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.38 _reflns_number_total 4802 _reflns_number_gt 3024 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0639P)^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 4802 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0474 _refine_ls_wR_factor_ref 0.1280 _refine_ls_wR_factor_gt 0.1205 _refine_ls_goodness_of_fit_ref 0.894 _refine_ls_restrained_S_all 0.894 _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 0.18480(2) 0.280884(13) 0.5000 0.05265(16) Uani 1 2 d S . . O1 O 0.13704(12) 0.23901(6) 0.44164(7) 0.0708(5) Uani 1 1 d . . . O2 O 0.24633(12) 0.18640(6) 0.44163(7) 0.0727(5) Uani 1 1 d . . . O3 O 0.0772(2) 0.32903(12) 0.5000 0.1170(11) Uani 1 2 d S . . N1 N 0.0000 0.09965(9) 0.2500 0.0669(8) Uani 1 2 d S . . C1 C 0.17424(19) 0.20260(9) 0.42401(10) 0.0626(7) Uani 1 1 d . . . C2 C 0.12925(17) 0.17528(8) 0.37845(10) 0.0627(6) Uani 1 1 d . . . C3 C 0.16682(18) 0.13474(9) 0.35618(11) 0.0762(8) Uani 1 1 d . . . H3 H 0.2204 0.1240 0.3699 0.091 Uiso 1 1 calc R . . C4 C 0.12405(19) 0.10998(9) 0.31298(11) 0.0766(8) Uani 1 1 d . . . H4 H 0.1502 0.0833 0.2973 0.092 Uiso 1 1 calc R . . C5 C 0.04298(19) 0.12482(8) 0.29343(10) 0.0684(7) Uani 1 1 d . . . C6 C 0.00706(18) 0.16511(9) 0.31574(12) 0.0772(8) Uani 1 1 d . . . H6 H -0.0469 0.1757 0.3026 0.093 Uiso 1 1 calc R . . C7 C 0.04975(19) 0.19018(9) 0.35739(12) 0.0804(8) Uani 1 1 d . . . H7 H 0.0245 0.2177 0.3716 0.096 Uiso 1 1 calc R . . C8 C 0.0000 0.04979(11) 0.2500 0.0576(9) Uani 1 2 d S . . C9 C -0.00185(17) 0.02439(8) 0.29995(10) 0.0670(7) Uani 1 1 d . . . H9 H -0.0057 0.0404 0.3343 0.080 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 0.0638(3) 0.0470(3) 0.0471(2) 0.000 0.000 -0.00572(19) O1 0.0848(12) 0.0597(11) 0.0679(11) -0.0143(9) -0.0108(9) -0.0002(9) O2 0.0822(12) 0.0656(12) 0.0703(11) -0.0139(9) -0.0180(9) -0.0030(10) O3 0.106(2) 0.110(2) 0.135(3) 0.000 0.000 0.0296(19) N1 0.101(2) 0.0438(17) 0.0557(17) 0.000 -0.0300(15) 0.000 C1 0.087(2) 0.0556(15) 0.0449(14) 0.0004(11) -0.0082(13) -0.0203(14) C2 0.0836(18) 0.0496(15) 0.0549(14) 0.0001(11) -0.0118(13) -0.0084(13) C3 0.090(2) 0.0637(17) 0.0749(18) -0.0096(14) -0.0262(15) -0.0015(14) C4 0.097(2) 0.0577(17) 0.0754(18) -0.0115(13) -0.0193(16) 0.0086(14) C5 0.100(2) 0.0494(15) 0.0554(14) 0.0000(12) -0.0259(14) -0.0012(14) C6 0.0899(19) 0.0655(18) 0.0763(18) -0.0146(14) -0.0327(15) 0.0175(14) C7 0.105(2) 0.0557(17) 0.0800(18) -0.0194(14) -0.0278(17) 0.0107(15) C8 0.089(2) 0.0387(18) 0.0448(19) 0.000 -0.0179(16) 0.000 C9 0.109(2) 0.0503(13) 0.0416(13) -0.0060(11) -0.0039(13) -0.0006(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.9571(16) . ? Cu1 O1 1.9571(16) 10_556 ? Cu1 O2 1.9640(16) 13_556 ? Cu1 O2 1.9640(16) 6 ? Cu1 O3 2.133(3) . ? Cu1 Cu1 2.6478(8) 13_556 ? O1 C1 1.247(3) . ? O2 C1 1.262(3) . ? O2 Cu1 1.9640(16) 13_556 ? N1 C5 1.410(3) . ? N1 C5 1.410(3) 3 ? N1 C8 1.410(4) . ? C1 C2 1.491(3) . ? C2 C7 1.377(3) . ? C2 C3 1.385(3) . ? C3 C4 1.398(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(3) . ? C4 H4 0.9300 . ? C5 C6 1.370(3) . ? C6 C7 1.376(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.381(3) 3 ? C8 C9 1.381(3) . ? C9 C9 1.381(4) 2 ? C9 H9 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 O1 89.43(10) . 10_556 ? O1 Cu1 O2 167.90(8) . 13_556 ? O1 Cu1 O2 89.49(7) 10_556 13_556 ? O1 Cu1 O2 89.49(7) . 6 ? O1 Cu1 O2 167.90(8) 10_556 6 ? O2 Cu1 O2 89.05(10) 13_556 6 ? O1 Cu1 O3 95.73(8) . . ? O1 Cu1 O3 95.73(8) 10_556 . ? O2 Cu1 O3 96.37(8) 13_556 . ? O2 Cu1 O3 96.37(8) 6 . ? O1 Cu1 Cu1 83.13(5) . 13_556 ? O1 Cu1 Cu1 83.13(5) 10_556 13_556 ? O2 Cu1 Cu1 84.78(5) 13_556 13_556 ? O2 Cu1 Cu1 84.78(5) 6 13_556 ? O3 Cu1 Cu1 178.38(9) . 13_556 ? C1 O1 Cu1 124.40(16) . . ? C1 O2 Cu1 121.74(16) . 13_556 ? C5 N1 C5 119.3(3) . 3 ? C5 N1 C8 120.34(13) . . ? C5 N1 C8 120.34(13) 3 . ? O1 C1 O2 125.9(2) . . ? O1 C1 C2 117.3(2) . . ? O2 C1 C2 116.8(2) . . ? C7 C2 C3 118.7(2) . . ? C7 C2 C1 120.5(2) . . ? C3 C2 C1 120.8(2) . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C6 C5 C4 118.8(2) . . ? C6 C5 N1 120.9(2) . . ? C4 C5 N1 120.3(2) . . ? C5 C6 C7 120.9(2) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C6 C7 C2 121.1(2) . . ? C6 C7 H7 119.4 . . ? C2 C7 H7 119.4 . . ? C9 C8 C9 117.3(3) 3 . ? C9 C8 N1 121.36(14) 3 . ? C9 C8 N1 121.36(14) . . ? C8 C9 C9 121.28(15) . 2 ? C8 C9 H9 119.4 . . ? C9 C9 H9 119.4 2 . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.38 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.564 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.047 data_xamd369s _database_code_depnum_ccdc_archive 'CCDC 269581' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common none _chemical_melting_point 'not measured' _chemical_formula_moiety 'Cu2 (C34 H20 N2 O8) 2(H2O)' _chemical_formula_sum 'C34 H24 Cu2 N2 O10' _chemical_formula_weight 747.63 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 Imma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y+1/2, z' '-x, y+1/2, -z' 'x, -y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1, z+1/2' '-x+1/2, y+1, -z+1/2' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x, y-1/2, -z' 'x, -y-1/2, z' '-x, y, z' '-x+1/2, -y+1/2, -z+1/2' 'x+1/2, y, -z+1/2' 'x+1/2, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 23.712(4) _cell_length_b 27.877(4) _cell_length_c 15.376(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10164(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6593 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 22.67 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 0.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1520 _exptl_absorpt_coefficient_mu 0.438 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.824 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details sadas _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _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_% none _diffrn_reflns_number 31430 _diffrn_reflns_av_R_equivalents 0.0541 _diffrn_reflns_av_sigmaI/netI 0.0460 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.53 _reflns_number_total 5511 _reflns_number_gt 3767 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.1026P)^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 5511 _refine_ls_number_parameters 113 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1506 _refine_ls_wR_factor_gt 0.1443 _refine_ls_goodness_of_fit_ref 0.927 _refine_ls_restrained_S_all 0.927 _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 0.0000 0.468000(11) -0.06300(2) 0.05043(15) Uani 1 2 d S . . O1 O -0.05831(6) 0.50939(5) -0.11272(11) 0.0703(4) Uani 1 1 d . . . O2 O -0.05801(6) 0.56382(5) -0.00670(12) 0.0715(4) Uani 1 1 d . . . O3 O 0.0000 0.41685(11) -0.16586(19) 0.1078(9) Uani 1 2 d S . . N1 N -0.2500 0.64918(9) -0.2500 0.0887(11) Uani 1 2 d S . . C1 C -0.07550(9) 0.54713(8) -0.07778(17) 0.0610(6) Uani 1 1 d . . . C2 C -0.12073(9) 0.57448(8) -0.12261(17) 0.0676(6) Uani 1 1 d . . . C3 C -0.14149(11) 0.61659(9) -0.0891(2) 0.0819(8) Uani 1 1 d . . . H3 H -0.1265 0.6287 -0.0377 0.098 Uiso 1 1 calc R . . C4 C -0.18436(11) 0.64133(9) -0.1306(2) 0.0901(9) Uani 1 1 d . . . H4 H -0.1984 0.6695 -0.1064 0.108 Uiso 1 1 calc R . . C5 C -0.20619(10) 0.62427(8) -0.20784(19) 0.0783(8) Uani 1 1 d . . . C6 C -0.18545(11) 0.58223(9) -0.2427(2) 0.0921(9) Uani 1 1 d . . . H6 H -0.2001 0.5705 -0.2947 0.111 Uiso 1 1 calc R . . C7 C -0.14265(10) 0.55735(9) -0.20032(19) 0.0818(8) Uani 1 1 d . . . H7 H -0.1287 0.5291 -0.2242 0.098 Uiso 1 1 calc R . . C8 C -0.2500 0.69996(10) -0.2500 0.0773(11) Uani 1 2 d S . . C9 C -0.29861(10) 0.72542(8) -0.2328(2) 0.0876(9) Uani 1 1 d . . . H9 H -0.3319 0.7090 -0.2210 0.105 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 0.03792(19) 0.0452(2) 0.0682(3) 0.00963(16) 0.000 0.000 O1 0.0579(8) 0.0613(10) 0.0918(12) 0.0068(9) -0.0135(8) 0.0125(7) O2 0.0595(8) 0.0619(9) 0.0931(12) 0.0103(9) -0.0161(9) 0.0127(7) O3 0.117(2) 0.105(2) 0.102(2) -0.0299(17) 0.000 0.000 N1 0.0760(18) 0.0404(13) 0.150(3) 0.000 -0.0654(19) 0.000 C1 0.0421(10) 0.0541(12) 0.0867(17) 0.0182(11) -0.0109(10) -0.0016(9) C2 0.0516(11) 0.0527(12) 0.0985(18) 0.0144(12) -0.0184(12) 0.0022(9) C3 0.0760(16) 0.0590(14) 0.111(2) -0.0032(13) -0.0420(15) 0.0125(12) C4 0.0876(17) 0.0552(14) 0.127(2) -0.0167(15) -0.0457(17) 0.0195(12) C5 0.0656(14) 0.0445(11) 0.125(2) 0.0029(13) -0.0473(14) 0.0001(10) C6 0.0912(18) 0.0587(14) 0.126(2) -0.0134(15) -0.0560(17) 0.0142(13) C7 0.0738(15) 0.0581(14) 0.114(2) -0.0063(14) -0.0350(15) 0.0149(11) C8 0.0604(18) 0.0408(15) 0.131(3) 0.000 -0.0510(19) 0.000 C9 0.0569(13) 0.0518(12) 0.154(3) 0.0088(15) -0.0445(15) -0.0071(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 O1 1.9563(14) . ? Cu1 O1 1.9563(14) 12 ? Cu1 O2 1.9565(15) 4_565 ? Cu1 O2 1.9565(15) 9_565 ? Cu1 O3 2.129(3) . ? Cu1 Cu1 2.6339(8) 9_565 ? O1 C1 1.250(3) . ? O2 C1 1.258(3) . ? O2 Cu1 1.9565(15) 9_565 ? N1 C5 1.408(2) 7_444 ? N1 C5 1.408(2) . ? N1 C8 1.416(4) . ? C1 C2 1.486(3) . ? C2 C3 1.373(3) . ? C2 C7 1.388(3) . ? C3 C4 1.384(3) . ? C3 H3 0.9300 . ? C4 C5 1.380(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C6 C7 1.392(3) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.380(3) . ? C8 C9 1.380(3) 7_444 ? C9 C9 1.370(4) 11_575 ? C9 H9 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 O1 89.94(9) . 12 ? O1 Cu1 O2 89.12(7) . 4_565 ? O1 Cu1 O2 168.06(7) 12 4_565 ? O1 Cu1 O2 168.06(7) . 9_565 ? O1 Cu1 O2 89.12(7) 12 9_565 ? O2 Cu1 O2 89.35(10) 4_565 9_565 ? O1 Cu1 O3 96.01(8) . . ? O1 Cu1 O3 96.01(8) 12 . ? O2 Cu1 O3 95.93(8) 4_565 . ? O2 Cu1 O3 95.93(8) 9_565 . ? O1 Cu1 Cu1 83.57(5) . 9_565 ? O1 Cu1 Cu1 83.57(5) 12 9_565 ? O2 Cu1 Cu1 84.50(5) 4_565 9_565 ? O2 Cu1 Cu1 84.50(5) 9_565 9_565 ? O3 Cu1 Cu1 179.40(9) . 9_565 ? C1 O1 Cu1 123.99(15) . . ? C1 O2 Cu1 122.67(14) . 9_565 ? C5 N1 C5 120.9(2) 7_444 . ? C5 N1 C8 119.55(12) 7_444 . ? C5 N1 C8 119.55(12) . . ? O1 C1 O2 125.3(2) . . ? O1 C1 C2 117.9(2) . . ? O2 C1 C2 116.8(2) . . ? C3 C2 C7 118.9(2) . . ? C3 C2 C1 121.6(2) . . ? C7 C2 C1 119.6(2) . . ? C2 C3 C4 121.1(2) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.0(2) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C6 C5 C4 119.6(2) . . ? C6 C5 N1 120.2(2) . . ? C4 C5 N1 120.2(2) . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 120.0 . . ? C7 C6 H6 120.0 . . ? C2 C7 C6 120.3(2) . . ? C2 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C9 118.1(3) . 7_444 ? C9 C8 N1 120.97(14) . . ? C9 C8 N1 120.97(14) 7_444 . ? C9 C9 C8 120.97(14) 11_575 . ? C9 C9 H9 119.5 11_575 . ? C8 C9 H9 119.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.640 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.144