# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Mike Zaworotko' 'Beth Rather' _publ_contact_author_name 'Dr Mike Zaworotko' _publ_contact_author_address ; Chemistry University of South Florida 4202 E. Fowler Avenue Tampa Florida 33620 UNITED STATES OF AMERICA ; _publ_contact_author_email XTAL@USF.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; A novel 3D network, [Cu2(glutarate)2(4,4'-bipyridine)]3H2O, that exhibits single-crystal to single-crystal dehydration and rehydration ; data_compound1a _database_code_CSD 203221 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C20 H20 Cu2 N2 O8)n,3n(H2 O1)' _chemical_formula_sum 'C20 H26 Cu2 N2 O11' _chemical_formula_weight 597.51 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.191(2) _cell_length_b 13.1900(13) _cell_length_c 8.5212(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.314(2) _cell_angle_gamma 90.00 _cell_volume 2343.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3966 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 27.47 _exptl_crystal_description diamondoid _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 1.878 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.8428 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_% ? _diffrn_reflns_number 7149 _diffrn_reflns_av_R_equivalents 0.0322 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2670 _reflns_number_gt 2293 _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^)+(0.0422P)^2^+7.3782P] 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 2670 _refine_ls_number_parameters 159 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0963 _refine_ls_wR_factor_gt 0.0921 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.048 _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 0.302578(15) 0.29418(2) 0.07530(4) 0.00904(12) Uani 1 1 d . . . N1 N 0.38018(11) 0.37120(18) 0.2280(3) 0.0128(5) Uani 1 1 d . . . O1 O 0.33309(9) 0.15576(14) 0.1327(2) 0.0154(4) Uani 1 1 d . . . O2 O 0.24287(10) 0.08145(15) 0.0105(3) 0.0178(5) Uani 1 1 d . . . O3 O 0.24736(10) -0.20910(15) 0.2504(2) 0.0152(4) Uani 1 1 d . . . O4 O 0.33894(10) -0.27626(16) 0.3790(2) 0.0185(5) Uani 1 1 d . . . C1 C 0.29801(13) 0.0793(2) 0.0937(3) 0.0107(5) Uani 1 1 d . . . C2 C 0.32452(14) -0.0221(2) 0.1578(3) 0.0134(6) Uani 1 1 d . . . H2A H 0.3050 -0.0398 0.2515 0.016 Uiso 1 1 calc R . . H2B H 0.3713 -0.0150 0.1952 0.016 Uiso 1 1 calc R . . C3 C 0.31291(14) -0.1096(2) 0.0384(3) 0.0128(5) Uani 1 1 d . . . H3A H 0.3358 -0.0959 -0.0511 0.015 Uiso 1 1 calc R . . H3B H 0.2665 -0.1145 -0.0058 0.015 Uiso 1 1 calc R . . C4 C 0.33629(14) -0.2106(2) 0.1173(3) 0.0134(5) Uani 1 1 d . . . H4A H 0.3265 -0.2658 0.0380 0.016 Uiso 1 1 calc R . . H4B H 0.3834 -0.2078 0.1520 0.016 Uiso 1 1 calc R . . C5 C 0.30516(14) -0.23412(19) 0.2597(3) 0.0112(5) Uani 1 1 d . . . C6 C 0.38065(15) 0.4719(2) 0.2398(4) 0.0250(7) Uani 1 1 d . . . H6 H 0.3482 0.5093 0.1728 0.030 Uiso 1 1 calc R . . C7 C 0.42627(16) 0.5243(2) 0.3453(5) 0.0300(8) Uani 1 1 d . . . H7 H 0.4243 0.5962 0.3500 0.036 Uiso 1 1 calc R . . C8 C 0.47476(13) 0.4730(2) 0.4440(3) 0.0132(6) Uani 1 1 d . . . C9 C 0.47340(15) 0.3680(2) 0.4330(4) 0.0198(6) Uani 1 1 d . . . H9 H 0.5049 0.3286 0.4995 0.024 Uiso 1 1 calc R . . C10 C 0.42610(15) 0.3212(2) 0.3252(4) 0.0208(7) Uani 1 1 d . . . H10 H 0.4262 0.2492 0.3198 0.025 Uiso 1 1 calc R . . O1W O 0.5000 0.9756(5) 0.2500 0.0814(18) Uani 1 2 d S . . H11W H 0.5000 0.8956 0.2500 0.098 Uiso 1 2 d SRD . . H12W H 0.4954 1.0185 0.3521 0.098 Uiso 0.50 1 d PRD . . O2W O 0.45736(17) 0.8712(3) 0.4985(6) 0.0847(14) Uani 1 1 d D . . H21W H 0.4606 0.8583 0.6250 0.102 Uiso 1 1 d RD . . H22W H 0.4985 0.9267 0.4821 0.102 Uiso 1 1 d RD . . 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 0.00926(18) 0.00775(18) 0.00951(18) -0.00072(12) 0.00002(12) -0.00140(13) N1 0.0113(11) 0.0133(11) 0.0139(11) -0.0024(9) 0.0019(9) -0.0017(9) O1 0.0128(10) 0.0097(9) 0.0225(11) -0.0013(8) -0.0001(8) 0.0007(8) O2 0.0166(10) 0.0112(10) 0.0223(11) 0.0022(8) -0.0057(9) -0.0029(8) O3 0.0114(10) 0.0202(10) 0.0135(10) 0.0033(8) 0.0011(8) 0.0009(8) O4 0.0171(11) 0.0267(11) 0.0123(10) 0.0054(8) 0.0044(8) 0.0094(9) C1 0.0135(13) 0.0103(12) 0.0085(13) 0.0007(9) 0.0025(10) 0.0001(10) C2 0.0166(14) 0.0097(13) 0.0127(13) 0.0014(10) -0.0008(11) -0.0003(11) C3 0.0185(14) 0.0095(12) 0.0111(13) 0.0023(10) 0.0048(11) 0.0009(11) C4 0.0166(14) 0.0103(13) 0.0145(13) 0.0001(10) 0.0061(11) 0.0014(11) C5 0.0164(14) 0.0042(12) 0.0128(13) -0.0018(9) 0.0025(11) -0.0016(10) C6 0.0180(16) 0.0162(15) 0.0347(18) -0.0083(13) -0.0123(14) 0.0047(12) C7 0.0198(17) 0.0141(15) 0.048(2) -0.0118(14) -0.0156(15) 0.0047(13) C8 0.0101(13) 0.0162(14) 0.0129(13) -0.0057(11) 0.0014(11) -0.0027(11) C9 0.0216(16) 0.0145(14) 0.0191(15) 0.0027(11) -0.0074(12) -0.0045(12) C10 0.0218(16) 0.0121(13) 0.0244(16) 0.0031(12) -0.0075(13) -0.0065(12) O1W 0.032(3) 0.084(4) 0.132(5) 0.000 0.025(3) 0.000 O2W 0.0390(19) 0.054(2) 0.161(4) 0.032(3) 0.018(2) -0.0032(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 Cu1 O1 1.969(2) . ? Cu1 O3 1.972(2) 4 ? Cu1 O2 1.975(2) 7 ? Cu1 O4 1.977(2) 6 ? Cu1 N1 2.159(2) . ? Cu1 Cu1 2.6357(7) 7 ? N1 C6 1.332(4) . ? N1 C10 1.334(4) . ? O1 C1 1.261(3) . ? O2 C1 1.254(3) . ? O2 Cu1 1.975(2) 7 ? O3 C5 1.257(3) . ? O3 Cu1 1.972(2) 4_545 ? O4 C5 1.263(3) . ? O4 Cu1 1.977(2) 6_556 ? C1 C2 1.514(4) . ? C2 C3 1.530(4) . ? C3 C4 1.533(4) . ? C4 C5 1.514(4) . ? C6 C7 1.382(4) . ? C7 C8 1.383(4) . ? C8 C9 1.388(4) . ? C8 C8 1.483(5) 5_666 ? C9 C10 1.379(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 Cu1 O3 89.38(8) . 4 ? O1 Cu1 O2 168.16(8) . 7 ? O3 Cu1 O2 90.29(9) 4 7 ? O1 Cu1 O4 86.50(9) . 6 ? O3 Cu1 O4 167.78(8) 4 6 ? O2 Cu1 O4 91.40(9) 7 6 ? O1 Cu1 N1 96.07(9) . . ? O3 Cu1 N1 90.57(8) 4 . ? O2 Cu1 N1 95.77(8) 7 . ? O4 Cu1 N1 101.30(9) 6 . ? O1 Cu1 Cu1 85.55(6) . 7 ? O3 Cu1 Cu1 80.57(6) 4 7 ? O2 Cu1 Cu1 82.72(6) 7 7 ? O4 Cu1 Cu1 87.64(6) 6 7 ? N1 Cu1 Cu1 170.99(6) . 7 ? C6 N1 C10 116.8(3) . . ? C6 N1 Cu1 120.6(2) . . ? C10 N1 Cu1 122.24(19) . . ? C1 O1 Cu1 121.59(18) . . ? C1 O2 Cu1 124.84(18) . 7 ? C5 O3 Cu1 127.31(18) . 4_545 ? C5 O4 Cu1 118.89(18) . 6_556 ? O2 C1 O1 125.2(3) . . ? O2 C1 C2 118.2(2) . . ? O1 C1 C2 116.6(2) . . ? C1 C2 C3 114.9(2) . . ? C2 C3 C4 111.3(2) . . ? C5 C4 C3 112.1(2) . . ? O3 C5 O4 124.9(3) . . ? O3 C5 C4 117.1(2) . . ? O4 C5 C4 118.1(2) . . ? N1 C6 C7 122.9(3) . . ? C6 C7 C8 120.5(3) . . ? C7 C8 C9 116.3(3) . . ? C7 C8 C8 121.9(3) . 5_666 ? C9 C8 C8 121.8(3) . 5_666 ? C10 C9 C8 119.7(3) . . ? N1 C10 C9 123.7(3) . . ? 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 C2 C3 C4 C5 56.7(3) . . . . ? C1 C2 C3 C4 -175.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.946 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.104 data_compound1b _database_code_CSD 203222 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C20 H20 Cu2 N2 O8)n' _chemical_formula_sum 'C20 H20 Cu2 N2 O8' _chemical_formula_weight 543.46 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.011(2) _cell_length_b 13.0520(14) _cell_length_c 8.5284(9) _cell_angle_alpha 90.00 _cell_angle_beta 100.679(2) _cell_angle_gamma 90.00 _cell_volume 2298.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3533 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 27.05 _exptl_crystal_description diamond _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.571 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.897 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_% ? _diffrn_reflns_number 7048 _diffrn_reflns_av_R_equivalents 0.0387 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.14 _reflns_number_total 2532 _reflns_number_gt 2145 _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^)+(0.0384P)^2^+4.1665P] 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 2532 _refine_ls_number_parameters 147 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0904 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 0.301817(14) 0.29578(2) 0.07435(3) 0.00961(11) Uani 1 1 d . . . N1 N 0.37960(11) 0.37295(17) 0.2273(2) 0.0136(5) Uani 1 1 d . . . O1 O 0.33367(9) 0.15761(13) 0.1341(2) 0.0150(4) Uani 1 1 d . . . O2 O 0.24473(9) 0.07939(13) 0.0089(2) 0.0163(4) Uani 1 1 d . . . O3 O 0.24745(9) -0.20605(14) 0.2518(2) 0.0149(4) Uani 1 1 d . . . O4 O 0.33755(9) -0.28031(14) 0.3788(2) 0.0167(4) Uani 1 1 d . . . C1 C 0.30023(12) 0.07989(19) 0.0933(3) 0.0115(5) Uani 1 1 d . . . C2 C 0.32857(14) -0.0213(2) 0.1552(3) 0.0154(6) Uani 1 1 d . . . H2A H 0.3122 -0.0381 0.2539 0.018 Uiso 1 1 calc R . . H2B H 0.3762 -0.0136 0.1847 0.018 Uiso 1 1 calc R . . C3 C 0.31398(13) -0.1112(2) 0.0407(3) 0.0142(5) Uani 1 1 d . . . H3A H 0.2668 -0.1145 -0.0004 0.017 Uiso 1 1 calc R . . H3B H 0.3359 -0.1003 -0.0513 0.017 Uiso 1 1 calc R . . C4 C 0.33649(13) -0.21210(19) 0.1209(3) 0.0131(5) Uani 1 1 d . . . H4A H 0.3268 -0.2682 0.0420 0.016 Uiso 1 1 calc R . . H4B H 0.3840 -0.2097 0.1578 0.016 Uiso 1 1 calc R . . C5 C 0.30442(13) -0.23499(19) 0.2612(3) 0.0117(5) Uani 1 1 d . . . C6 C 0.37956(16) 0.4727(3) 0.2441(5) 0.0416(10) Uani 1 1 d . . . H6 H 0.3461 0.5111 0.1798 0.050 Uiso 1 1 calc R . . C7 C 0.42551(17) 0.5246(3) 0.3500(5) 0.0526(13) Uani 1 1 d . . . H7 H 0.4230 0.5971 0.3579 0.063 Uiso 1 1 calc R . . C8 C 0.47466(13) 0.4730(2) 0.4439(3) 0.0168(6) Uani 1 1 d . . . C9 C 0.47349(15) 0.3690(2) 0.4294(4) 0.0260(7) Uani 1 1 d . . . H9 H 0.5056 0.3287 0.4948 0.031 Uiso 1 1 calc R . . C10 C 0.42608(16) 0.3225(2) 0.3208(4) 0.0281(7) Uani 1 1 d . . . H10 H 0.4268 0.2500 0.3124 0.034 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 0.01060(18) 0.00801(17) 0.00926(18) -0.00130(11) -0.00067(12) -0.00176(11) N1 0.0119(11) 0.0167(11) 0.0119(11) -0.0040(9) 0.0017(9) -0.0035(9) O1 0.0144(10) 0.0095(9) 0.0199(10) -0.0003(8) 0.0001(8) 0.0000(7) O2 0.0162(10) 0.0100(9) 0.0193(10) 0.0011(7) -0.0056(8) -0.0012(7) O3 0.0127(9) 0.0187(10) 0.0131(9) 0.0027(7) 0.0017(7) 0.0025(7) O4 0.0169(10) 0.0207(10) 0.0128(9) 0.0059(8) 0.0032(8) 0.0082(8) C1 0.0155(13) 0.0110(12) 0.0083(12) -0.0004(9) 0.0032(10) 0.0013(10) C2 0.0191(14) 0.0110(12) 0.0138(13) 0.0008(10) -0.0029(11) 0.0010(10) C3 0.0194(14) 0.0113(12) 0.0114(12) 0.0016(10) 0.0018(11) 0.0003(10) C4 0.0174(14) 0.0092(12) 0.0128(12) 0.0005(9) 0.0028(11) 0.0021(10) C5 0.0147(13) 0.0067(11) 0.0132(12) -0.0019(10) 0.0011(10) -0.0009(10) C6 0.0221(17) 0.0206(16) 0.069(3) -0.0225(17) -0.0259(17) 0.0105(13) C7 0.0262(19) 0.0224(18) 0.092(3) -0.035(2) -0.035(2) 0.0137(14) C8 0.0103(13) 0.0243(14) 0.0159(13) -0.0110(11) 0.0024(11) -0.0019(11) C9 0.0290(17) 0.0189(15) 0.0231(15) 0.0090(12) -0.0135(13) -0.0102(12) C10 0.0368(19) 0.0133(14) 0.0260(16) 0.0062(12) -0.0153(14) -0.0096(13) _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 1.9579(18) . ? Cu1 O3 1.9596(18) 4 ? Cu1 O4 1.9622(19) 6 ? Cu1 O2 1.9641(18) 7 ? Cu1 N1 2.144(2) . ? Cu1 Cu1 2.5989(6) 7 ? N1 C6 1.310(4) . ? N1 C10 1.317(4) . ? O1 C1 1.246(3) . ? O2 C1 1.252(3) . ? O2 Cu1 1.9641(18) 7 ? O3 C5 1.244(3) . ? O3 Cu1 1.9596(18) 4_545 ? O4 C5 1.257(3) . ? O4 Cu1 1.9622(18) 6_556 ? C1 C2 1.504(3) . ? C2 C3 1.521(4) . ? C3 C4 1.519(3) . ? C4 C5 1.507(3) . ? C6 C7 1.372(4) . ? C7 C8 1.362(4) . ? C8 C9 1.362(4) . ? C8 C8 1.473(5) 5_666 ? C9 C10 1.370(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 Cu1 O3 89.71(8) . 4 ? O1 Cu1 O4 87.72(8) . 6 ? O3 Cu1 O4 168.79(7) 4 6 ? O1 Cu1 O2 168.94(8) . 7 ? O3 Cu1 O2 89.21(8) 4 7 ? O4 Cu1 O2 91.23(8) 6 7 ? O1 Cu1 N1 95.12(8) . . ? O3 Cu1 N1 89.73(8) 4 . ? O4 Cu1 N1 101.36(8) 6 . ? O2 Cu1 N1 95.89(8) 7 . ? O1 Cu1 Cu1 85.32(5) . 7 ? O3 Cu1 Cu1 81.45(6) 4 7 ? O4 Cu1 Cu1 87.47(6) 6 7 ? O2 Cu1 Cu1 83.63(5) 7 7 ? N1 Cu1 Cu1 171.17(6) . 7 ? C6 N1 C10 116.5(3) . . ? C6 N1 Cu1 121.2(2) . . ? C10 N1 Cu1 121.98(19) . . ? C1 O1 Cu1 121.96(17) . . ? C1 O2 Cu1 123.50(16) . 7 ? C5 O3 Cu1 126.30(17) . 4_545 ? C5 O4 Cu1 118.94(17) . 6_556 ? O1 C1 O2 125.6(2) . . ? O1 C1 C2 116.8(2) . . ? O2 C1 C2 117.6(2) . . ? C1 C2 C3 115.6(2) . . ? C4 C3 C2 111.7(2) . . ? C5 C4 C3 112.4(2) . . ? O3 C5 O4 125.3(2) . . ? O3 C5 C4 117.1(2) . . ? O4 C5 C4 117.6(2) . . ? N1 C6 C7 123.2(3) . . ? C8 C7 C6 120.5(3) . . ? C7 C8 C9 116.1(3) . . ? C7 C8 C8 121.6(3) . 5_666 ? C9 C8 C8 122.3(3) . 5_666 ? C8 C9 C10 120.1(3) . . ? N1 C10 C9 123.5(3) . . ? 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 C2 C3 C4 C5 59.8(3) . . . . ? C1 C2 C3 C4 -172.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.14 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.533 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.094 data_compound1c _database_code_CSD 203223 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C20 H20 Cu2 N2 O8)n,3n(H2 O1)' _chemical_formula_sum 'C20 H20 Cu2 N2 O11' _chemical_formula_weight 591.46 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.351(2) _cell_length_b 13.1381(13) _cell_length_c 8.5699(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.007(2) _cell_angle_gamma 90.00 _cell_volume 2359.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4335 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 27.11 _exptl_crystal_description diamondoid _exptl_crystal_colour green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.665 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 1.864 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.8057 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_% ? _diffrn_reflns_number 6920 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0387 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 27.12 _reflns_number_total 2582 _reflns_number_gt 2227 _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^)+(0.0637P)^2^+3.7481P] 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 2582 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1112 _refine_ls_wR_factor_gt 0.1071 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.302182(15) 0.29456(3) 0.07568(4) 0.01228(14) Uani 1 1 d . . . N1 N 0.37958(11) 0.3723(2) 0.2283(3) 0.0164(5) Uani 1 1 d . . . O1 O 0.33266(10) 0.15573(16) 0.1346(3) 0.0184(5) Uani 1 1 d . . . O2 O 0.24366(10) 0.08061(16) 0.0091(3) 0.0211(5) Uani 1 1 d . . . O3 O 0.24667(10) -0.20829(16) 0.2512(3) 0.0184(5) Uani 1 1 d . . . O4 O 0.33698(11) -0.27828(17) 0.3801(3) 0.0217(5) Uani 1 1 d . . . C1 C 0.29854(14) 0.0790(2) 0.0941(3) 0.0146(6) Uani 1 1 d . . . C2 C 0.32458(15) -0.0224(2) 0.1583(3) 0.0173(6) Uani 1 1 d . . . H2A H 0.3058 -0.0392 0.2522 0.021 Uiso 1 1 calc R . . H2B H 0.3712 -0.0156 0.1951 0.021 Uiso 1 1 calc R . . C3 C 0.31212(15) -0.1107(2) 0.0414(3) 0.0172(6) Uani 1 1 d . . . H3A H 0.3346 -0.0981 -0.0476 0.021 Uiso 1 1 calc R . . H3B H 0.2658 -0.1147 -0.0030 0.021 Uiso 1 1 calc R . . C4 C 0.33457(15) -0.2124(2) 0.1204(4) 0.0171(6) Uani 1 1 d . . . H4A H 0.3244 -0.2677 0.0412 0.020 Uiso 1 1 calc R . . H4B H 0.3815 -0.2106 0.1561 0.020 Uiso 1 1 calc R . . C5 C 0.30359(14) -0.2352(2) 0.2614(3) 0.0149(6) Uani 1 1 d . . . C6 C 0.38007(17) 0.4726(3) 0.2419(5) 0.0393(11) Uani 1 1 d . . . H6 H 0.3473 0.5104 0.1764 0.047 Uiso 1 1 calc R . . C7 C 0.42610(19) 0.5249(3) 0.3469(6) 0.0469(13) Uani 1 1 d . . . H7 H 0.4244 0.5971 0.3521 0.056 Uiso 1 1 calc R . . C8 C 0.47442(14) 0.4730(2) 0.4440(3) 0.0166(6) Uani 1 1 d . . . C9 C 0.47312(17) 0.3688(3) 0.4310(4) 0.0301(8) Uani 1 1 d . . . H9 H 0.5050 0.3289 0.4956 0.036 Uiso 1 1 calc R . . C10 C 0.42512(18) 0.3222(3) 0.3233(4) 0.0305(8) Uani 1 1 d . . . H10 H 0.4250 0.2500 0.3175 0.037 Uiso 1 1 calc R . . O1AW O 0.5000 0.902(5) 0.2500 0.220(17) Uani 0.50 2 d SP . . O1BW O 0.5000 1.0335(18) 0.2500 0.213(18) Uani 0.50 2 d SP . . O2W O 0.5065(13) 0.899(4) 0.085(6) 0.23(3) Uani 0.33 1 d P . . O3W O 0.5416(6) 0.8683(13) -0.027(3) 0.143(9) Uani 0.33 1 d P . . O4W O 0.4988(15) 0.975(3) 0.156(13) 0.53(12) Uani 0.33 1 d P . . 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 0.0149(2) 0.0096(2) 0.0106(2) -0.00126(13) -0.00188(13) -0.00184(13) N1 0.0158(11) 0.0177(13) 0.0144(12) -0.0027(10) -0.0007(10) -0.0042(10) O1 0.0185(10) 0.0112(10) 0.0234(11) -0.0005(9) -0.0011(9) 0.0001(8) O2 0.0236(11) 0.0127(11) 0.0217(11) 0.0024(9) -0.0091(9) -0.0022(9) O3 0.0186(10) 0.0204(11) 0.0150(10) 0.0024(9) 0.0000(8) 0.0016(8) O4 0.0231(11) 0.0259(12) 0.0157(11) 0.0072(9) 0.0023(9) 0.0100(9) C1 0.0210(14) 0.0126(14) 0.0098(13) 0.0005(11) 0.0017(11) 0.0012(11) C2 0.0238(15) 0.0124(14) 0.0135(14) 0.0026(12) -0.0024(12) 0.0008(12) C3 0.0264(15) 0.0132(14) 0.0109(13) 0.0003(12) 0.0013(12) -0.0005(12) C4 0.0255(15) 0.0105(14) 0.0148(14) 0.0000(11) 0.0031(12) 0.0030(11) C5 0.0214(14) 0.0088(13) 0.0130(14) -0.0024(11) -0.0006(11) -0.0002(11) C6 0.0259(17) 0.0183(17) 0.061(3) -0.0134(18) -0.0244(17) 0.0058(14) C7 0.034(2) 0.0157(17) 0.075(3) -0.0215(19) -0.029(2) 0.0091(15) C8 0.0153(13) 0.0181(15) 0.0156(14) -0.0062(12) 0.0009(11) -0.0030(12) C9 0.0329(18) 0.0176(16) 0.0305(19) 0.0050(14) -0.0178(15) -0.0058(14) C10 0.0357(19) 0.0143(15) 0.033(2) 0.0016(14) -0.0162(16) -0.0068(14) O1AW 0.020(8) 0.31(6) 0.32(6) 0.000 0.020(18) 0.000 O1BW 0.032(8) 0.099(15) 0.50(6) 0.000 0.036(17) 0.000 O2W 0.077(16) 0.29(5) 0.33(5) -0.22(5) 0.02(2) -0.02(2) O3W 0.041(7) 0.097(12) 0.30(3) -0.083(15) 0.055(11) -0.033(7) O4W 0.043(11) 0.15(3) 1.3(3) -0.33(7) -0.24(9) 0.06(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 O1 1.970(2) . ? Cu1 O3 1.970(2) 4 ? Cu1 O4 1.970(2) 6 ? Cu1 O2 1.976(2) 7 ? Cu1 N1 2.159(2) . ? Cu1 Cu1 2.6297(7) 7 ? N1 C10 1.319(4) . ? N1 C6 1.322(4) . ? O1 C1 1.254(4) . ? O2 C1 1.256(3) . ? O2 Cu1 1.976(2) 7 ? O3 C5 1.253(4) . ? O3 Cu1 1.970(2) 4_545 ? O4 C5 1.260(4) . ? O4 Cu1 1.970(2) 6_556 ? C1 C2 1.505(4) . ? C2 C3 1.523(4) . ? C3 C4 1.532(4) . ? C4 C5 1.514(4) . ? C6 C7 1.382(5) . ? C7 C8 1.376(5) . ? C8 C9 1.373(4) . ? C8 C8 1.489(5) 5_666 ? C9 C10 1.384(4) . ? O1AW O4W 1.24(8) 2_655 ? O1AW O4W 1.24(8) . ? O1AW O2W 1.45(5) . ? O1AW O2W 1.45(5) 2_655 ? O1AW O1BW 1.73(6) . ? O1BW O4W 1.12(7) . ? O1BW O4W 1.12(7) 2_655 ? O2W O4W 1.19(5) . ? O2W O3W 1.38(4) . ? O4W O4W 1.6(2) 2_655 ? 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 O3 89.20(9) . 4 ? O1 Cu1 O4 87.57(10) . 6 ? O3 Cu1 O4 168.05(9) 4 6 ? O1 Cu1 O2 168.26(8) . 7 ? O3 Cu1 O2 89.78(10) 4 7 ? O4 Cu1 O2 91.05(10) 6 7 ? O1 Cu1 N1 96.08(9) . . ? O3 Cu1 N1 90.39(9) 4 . ? O4 Cu1 N1 101.39(9) 6 . ? O2 Cu1 N1 95.62(9) 7 . ? O1 Cu1 Cu1 85.49(6) . 7 ? O3 Cu1 Cu1 80.92(6) 4 7 ? O4 Cu1 Cu1 87.35(6) 6 7 ? O2 Cu1 Cu1 82.80(6) 7 7 ? N1 Cu1 Cu1 171.17(7) . 7 ? C10 N1 C6 116.8(3) . . ? C10 N1 Cu1 121.8(2) . . ? C6 N1 Cu1 121.1(2) . . ? C1 O1 Cu1 121.87(19) . . ? C1 O2 Cu1 124.7(2) . 7 ? C5 O3 Cu1 126.8(2) . 4_545 ? C5 O4 Cu1 119.3(2) . 6_556 ? O1 C1 O2 125.1(3) . . ? O1 C1 C2 117.1(2) . . ? O2 C1 C2 117.8(3) . . ? C1 C2 C3 115.3(2) . . ? C2 C3 C4 111.9(2) . . ? C5 C4 C3 112.2(2) . . ? O3 C5 O4 125.1(3) . . ? O3 C5 C4 117.0(3) . . ? O4 C5 C4 117.9(3) . . ? N1 C6 C7 123.1(3) . . ? C8 C7 C6 120.3(3) . . ? C9 C8 C7 116.3(3) . . ? C9 C8 C8 121.9(3) . 5_666 ? C7 C8 C8 121.8(4) . 5_666 ? C8 C9 C10 119.7(3) . . ? N1 C10 C9 123.8(3) . . ? O4W O1AW O4W 80(10) 2_655 . ? O4W O1AW O2W 131(9) 2_655 . ? O4W O1AW O2W 52(3) . . ? O4W O1AW O2W 52(3) 2_655 2_655 ? O4W O1AW O2W 131(9) . 2_655 ? O2W O1AW O2W 177(8) . 2_655 ? O4W O1AW O1BW 40(5) 2_655 . ? O4W O1AW O1BW 40(5) . . ? O2W O1AW O1BW 91(4) . . ? O2W O1AW O1BW 91(4) 2_655 . ? O4W O1BW O4W 92(10) . 2_655 ? O4W O1BW O1AW 46(5) . . ? O4W O1BW O1AW 46(5) 2_655 . ? O4W O2W O3W 138(8) . . ? O4W O2W O1AW 55(5) . . ? O3W O2W O1AW 148(4) . . ? O1BW O4W O2W 164(9) . . ? O1BW O4W O1AW 94(10) . . ? O2W O4W O1AW 73(4) . . ? O1BW O4W O4W 44(5) . 2_655 ? O2W O4W O4W 122(7) . 2_655 ? O1AW O4W O4W 50(5) . 2_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 C1 C2 C3 C4 -174.7(3) . . . . ? C2 C3 C4 C5 57.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.12 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.628 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.111 data_compound2a _database_code_CSD 203224 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C22 H24 Cu2 N2 O8)n,5n(H2 O1)' _chemical_formula_sum 'C22 H24 Cu2 N2 O13' _chemical_formula_weight 651.51 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.238(2) _cell_length_b 13.0527(13) _cell_length_c 8.6313(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.473(2) _cell_angle_gamma 90.00 _cell_volume 2729.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4845 _cell_measurement_theta_min 2.86 _cell_measurement_theta_max 27.44 _exptl_crystal_description diamondoid _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.585 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.625 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.858 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_% ? _diffrn_reflns_number 8295 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0370 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3082 _reflns_number_gt 2722 _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^)+(0.0358P)^2^+11.6842P] 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 3082 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.0972 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.003 _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 0.205251(14) 0.20430(3) 0.44606(4) 0.01417(11) Uani 1 1 d . . . N1 N 0.13951(9) 0.13937(18) 0.3045(3) 0.0161(5) Uani 1 1 d . . . O1 O 0.25668(9) 0.57640(15) 0.9927(2) 0.0215(4) Uani 1 1 d . . . O2 O 0.18014(9) 0.65457(16) 0.9084(3) 0.0231(5) Uani 1 1 d . . . O3 O 0.17339(9) 0.21662(17) 0.6536(2) 0.0259(5) Uani 1 1 d . . . O4 O 0.25045(9) 0.29039(16) 0.7429(2) 0.0222(4) Uani 1 1 d . . . C1 C 0.20882(12) 0.5758(2) 0.9326(3) 0.0171(6) Uani 1 1 d . . . C2 C 0.18388(13) 0.4753(2) 0.8800(3) 0.0222(6) Uani 1 1 d . . . H2A H 0.1973 0.4597 0.7753 0.027 Uiso 1 1 calc R . . H2B H 0.1433 0.4838 0.8710 0.027 Uiso 1 1 calc R . . C3 C 0.19634(13) 0.3840(2) 0.9847(3) 0.0201(6) Uani 1 1 d . . . H3A H 0.1784 0.3942 1.0854 0.024 Uiso 1 1 calc R . . H3B H 0.2367 0.3794 1.0047 0.024 Uiso 1 1 calc R . . C4 C 0.17566(13) 0.2840(2) 0.9113(3) 0.0200(6) Uani 1 1 d . . . H4A H 0.1837 0.2267 0.9835 0.024 Uiso 1 1 calc R . . H4B H 0.1351 0.2880 0.8952 0.024 Uiso 1 1 calc R . . C5 C 0.20203(12) 0.2618(2) 0.7574(3) 0.0175(6) Uani 1 1 d . . . C6 C 0.14480(12) 0.0455(2) 0.2452(3) 0.0192(6) Uani 1 1 d . . . H6 H 0.1743 0.0035 0.2821 0.023 Uiso 1 1 calc R . . C7 C 0.10891(12) 0.0069(2) 0.1318(3) 0.0221(6) Uani 1 1 d . . . H7 H 0.1140 -0.0603 0.0926 0.027 Uiso 1 1 calc R . . C8 C 0.06572(12) 0.0669(2) 0.0762(3) 0.0201(6) Uani 1 1 d . . . C9 C 0.06086(12) 0.1641(2) 0.1360(3) 0.0206(6) Uani 1 1 d . . . H9 H 0.0320 0.2080 0.1000 0.025 Uiso 1 1 calc R . . C10 C 0.09809(12) 0.1974(2) 0.2484(3) 0.0199(6) Uani 1 1 d . . . H10 H 0.0942 0.2649 0.2879 0.024 Uiso 1 1 calc R . . C11 C 0.02388(13) 0.0254(3) -0.0404(3) 0.0248(7) Uani 1 1 d . . . H11A H 0.0419 -0.0251 -0.1081 0.030 Uiso 1 1 calc R . . H11B H 0.0097 0.0821 -0.1064 0.030 Uiso 1 1 calc R . . O1W O 0.4936(4) 0.8438(14) 0.6260(14) 0.125(6) Uani 0.40 1 d P . . O2W O 0.568(2) 0.833(6) 0.591(6) 0.14(2) Uani 0.20 1 d P . . O3W O 0.5147(8) 0.9178(12) 0.395(2) 0.138(6) Uani 0.40 1 d P . . O4W O 0.4521(7) 0.9358(16) 0.391(3) 0.147(10) Uani 0.30 1 d P . . O5W O 0.548(2) 0.768(4) 0.675(6) 0.18(2) Uani 0.30 1 d P . . O6W O 0.5000 0.9251(17) 0.2500 0.22(2) Uani 0.40 2 d SP . . O7W O 0.5626(12) 0.907(2) 0.493(5) 0.123(11) Uani 0.20 1 d P . . O8W O 0.5519(6) 0.794(3) 0.632(2) 0.126(12) Uani 0.50 1 d P . . 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 0.01805(18) 0.01377(17) 0.01047(17) -0.00044(13) -0.00381(12) -0.00369(14) N1 0.0167(11) 0.0187(12) 0.0129(11) -0.0021(9) -0.0011(9) -0.0036(9) O1 0.0250(11) 0.0149(10) 0.0242(11) -0.0032(8) -0.0091(9) 0.0024(8) O2 0.0235(11) 0.0154(10) 0.0298(11) 0.0012(9) -0.0081(9) 0.0012(9) O3 0.0301(12) 0.0315(12) 0.0161(10) -0.0072(9) 0.0013(9) -0.0120(10) O4 0.0238(11) 0.0292(11) 0.0136(9) -0.0012(8) -0.0008(8) -0.0059(9) C1 0.0246(15) 0.0171(13) 0.0095(12) -0.0016(10) -0.0012(11) -0.0002(12) C2 0.0299(16) 0.0176(14) 0.0186(14) -0.0018(11) -0.0082(12) -0.0012(12) C3 0.0320(16) 0.0161(13) 0.0121(13) -0.0014(10) -0.0018(11) -0.0020(12) C4 0.0285(16) 0.0173(14) 0.0144(13) -0.0002(11) 0.0023(11) -0.0040(12) C5 0.0260(15) 0.0125(12) 0.0139(13) 0.0011(10) -0.0033(11) -0.0009(11) C6 0.0156(13) 0.0231(15) 0.0189(14) -0.0034(11) -0.0016(11) -0.0002(11) C7 0.0196(14) 0.0267(16) 0.0201(14) -0.0094(12) -0.0004(12) -0.0026(12) C8 0.0166(14) 0.0318(16) 0.0121(13) -0.0028(11) 0.0005(11) -0.0069(12) C9 0.0162(14) 0.0293(16) 0.0161(13) 0.0037(12) -0.0017(11) -0.0003(12) C10 0.0221(14) 0.0206(14) 0.0168(13) -0.0004(11) -0.0006(11) -0.0017(12) C11 0.0224(16) 0.0377(18) 0.0140(13) -0.0046(13) -0.0020(12) -0.0079(14) O1W 0.051(6) 0.238(17) 0.086(8) -0.070(10) -0.004(6) 0.015(8) O2W 0.09(3) 0.26(7) 0.08(3) 0.00(3) 0.01(2) 0.10(4) O3W 0.135(15) 0.135(14) 0.144(15) 0.007(11) -0.023(12) 0.050(11) O4W 0.072(12) 0.125(16) 0.24(3) -0.090(17) 0.004(14) -0.006(10) O5W 0.19(4) 0.16(3) 0.19(5) 0.02(3) -0.11(3) 0.05(3) O6W 0.30(5) 0.065(14) 0.29(5) 0.000 -0.18(5) 0.000 O7W 0.072(18) 0.10(2) 0.20(4) -0.06(2) 0.02(2) -0.012(15) O8W 0.027(5) 0.28(3) 0.065(11) -0.033(14) -0.012(6) -0.006(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 O2 1.965(2) 6_565 ? Cu1 O1 1.973(2) 4_546 ? Cu1 O3 1.975(2) . ? Cu1 O4 1.977(2) 7_556 ? Cu1 N1 2.157(2) . ? Cu1 Cu1 2.6253(7) 7_556 ? N1 C6 1.335(4) . ? N1 C10 1.339(4) . ? O1 C1 1.259(4) . ? O1 Cu1 1.973(2) 4_556 ? O2 C1 1.256(3) . ? O2 Cu1 1.965(2) 6_566 ? O3 C5 1.265(3) . ? O4 C5 1.241(4) . ? O4 Cu1 1.977(2) 7_556 ? C1 C2 1.509(4) . ? C2 C3 1.522(4) . ? C3 C4 1.530(4) . ? C4 C5 1.516(4) . ? C6 C7 1.387(4) . ? C7 C8 1.383(4) . ? C8 C9 1.376(4) . ? C8 C11 1.510(4) . ? C9 C10 1.378(4) . ? C11 C11 1.519(6) 5 ? O1W O8W 1.55(3) . ? O1W O5W 1.68(4) . ? O2W O8W 0.74(7) . ? O2W O5W 1.23(9) . ? O2W O7W 1.29(6) . ? O3W O6W 1.292(19) . ? O3W O7W 1.43(4) . ? O3W O4W 1.53(3) . ? O4W O6W 1.71(2) . ? O5W O8W 0.52(8) . ? O6W O3W 1.292(19) 2_655 ? O6W O4W 1.71(2) 2_655 ? 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 O2 Cu1 O1 168.11(9) 6_565 4_546 ? O2 Cu1 O3 86.97(9) 6_565 . ? O1 Cu1 O3 90.98(10) 4_546 . ? O2 Cu1 O4 90.18(9) 6_565 7_556 ? O1 Cu1 O4 89.45(9) 4_546 7_556 ? O3 Cu1 O4 168.13(9) . 7_556 ? O2 Cu1 N1 93.06(9) 6_565 . ? O1 Cu1 N1 98.79(9) 4_546 . ? O3 Cu1 N1 104.21(9) . . ? O4 Cu1 N1 87.43(9) 7_556 . ? O2 Cu1 Cu1 83.24(6) 6_565 7_556 ? O1 Cu1 Cu1 85.01(6) 4_546 7_556 ? O3 Cu1 Cu1 88.86(6) . 7_556 ? O4 Cu1 Cu1 79.36(6) 7_556 7_556 ? N1 Cu1 Cu1 166.25(6) . 7_556 ? C6 N1 C10 117.4(2) . . ? C6 N1 Cu1 120.07(19) . . ? C10 N1 Cu1 121.25(19) . . ? C1 O1 Cu1 122.38(18) . 4_556 ? C1 O2 Cu1 124.92(19) . 6_566 ? C5 O3 Cu1 117.40(19) . . ? C5 O4 Cu1 128.98(19) . 7_556 ? O2 C1 O1 124.3(3) . . ? O2 C1 C2 116.5(3) . . ? O1 C1 C2 119.2(3) . . ? C1 C2 C3 115.5(2) . . ? C2 C3 C4 111.4(2) . . ? C5 C4 C3 112.7(2) . . ? O4 C5 O3 124.9(3) . . ? O4 C5 C4 116.9(2) . . ? O3 C5 C4 118.3(3) . . ? N1 C6 C7 122.6(3) . . ? C8 C7 C6 119.7(3) . . ? C9 C8 C7 117.6(3) . . ? C9 C8 C11 121.2(3) . . ? C7 C8 C11 121.2(3) . . ? C8 C9 C10 119.6(3) . . ? N1 C10 C9 123.2(3) . . ? C8 C11 C11 110.9(3) . 5 ? O8W O1W O5W 18(3) . . ? O8W O2W O5W 10(3) . . ? O8W O2W O7W 140(7) . . ? O5W O2W O7W 149(5) . . ? O6W O3W O7W 142(2) . . ? O6W O3W O4W 73.9(16) . . ? O7W O3W O4W 144(2) . . ? O3W O4W O6W 46.5(10) . . ? O8W O5W O2W 14(5) . . ? O8W O5W O1W 67(5) . . ? O2W O5W O1W 77(3) . . ? O3W O6W O3W 172(3) 2_655 . ? O3W O6W O4W 59.6(12) 2_655 2_655 ? O3W O6W O4W 121.2(12) . 2_655 ? O3W O6W O4W 121.2(12) 2_655 . ? O3W O6W O4W 59.6(12) . . ? O4W O6W O4W 171(2) 2_655 . ? O2W O7W O3W 123(3) . . ? O5W O8W O2W 156(7) . . ? O5W O8W O1W 96(6) . . ? O2W O8W O1W 102(7) . . ? 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 C1 C2 C3 C4 -172.7(3) . . . . ? C2 C3 C4 C5 60.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.594 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.086 data_compound2b _database_code_CSD 203225 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C22 H24 Cu2 N2 O8)n,2n(H2 O1)' _chemical_formula_sum 'C22 H24 Cu2 N2 O10' _chemical_formula_weight 603.51 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 24.047(8) _cell_length_b 11.784(4) _cell_length_c 9.059(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.044(6) _cell_angle_gamma 90.00 _cell_volume 2566.4(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2097 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 25.00 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.713 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.4732 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_% ? _diffrn_reflns_number 6194 _diffrn_reflns_av_R_equivalents 0.0949 _diffrn_reflns_av_sigmaI/netI 0.1142 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 25.07 _reflns_number_total 2257 _reflns_number_gt 1583 _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^)+(0.0677P)^2^+2.7376P] 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 2257 _refine_ls_number_parameters 186 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1139 _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.1618 _refine_ls_wR_factor_gt 0.1487 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _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 0.20600(3) 0.22708(7) 0.41969(10) 0.0149(3) Uani 1 1 d . . . N1 N 0.1408(2) 0.1663(5) 0.2732(7) 0.0188(14) Uani 1 1 d . . . O1 O 0.2643(2) 0.5743(4) 1.0490(6) 0.0225(12) Uani 1 1 d . . . O2 O 0.18906(19) 0.6108(4) 0.9126(6) 0.0235(13) Uani 1 1 d . . . O3 O 0.16530(19) 0.2223(4) 0.6055(6) 0.0254(12) Uani 1 1 d . . . O4 O 0.24142(19) 0.2514(4) 0.7402(6) 0.0220(12) Uani 1 1 d . . . C1 C 0.2209(3) 0.5452(6) 0.9796(8) 0.0170(16) Uani 1 1 d . . . C2 C 0.2102(3) 0.4210(6) 0.9762(9) 0.0217(17) Uani 1 1 d . . . H2A H 0.2104 0.3928 1.0792 0.026 Uiso 1 1 calc R . . H2B H 0.2415 0.3838 0.9255 0.026 Uiso 1 1 calc R . . C3 C 0.1566(3) 0.3838(6) 0.9016(9) 0.0224(17) Uani 1 1 d . . . H3A H 0.1505 0.4298 0.8113 0.027 Uiso 1 1 calc R . . H3B H 0.1254 0.3990 0.9686 0.027 Uiso 1 1 calc R . . C4 C 0.1562(3) 0.2580(6) 0.8597(8) 0.0227(17) Uani 1 1 d . . . H4A H 0.1718 0.2121 0.9421 0.027 Uiso 1 1 calc R . . H4B H 0.1175 0.2325 0.8398 0.027 Uiso 1 1 calc R . . C5 C 0.1904(3) 0.2418(5) 0.7247(8) 0.0174(16) Uani 1 1 d . . . C6 C 0.1443(3) 0.0646(6) 0.2134(8) 0.0200(17) Uani 1 1 d . . . H6 H 0.1748 0.0177 0.2424 0.024 Uiso 1 1 calc R . . C7 C 0.1069(3) 0.0227(6) 0.1125(8) 0.0188(16) Uani 1 1 d . . . H7 H 0.1121 -0.0502 0.0702 0.023 Uiso 1 1 calc R . . C8 C 0.0610(3) 0.0886(6) 0.0723(8) 0.0160(16) Uani 1 1 d . . . C9 C 0.0576(3) 0.1941(6) 0.1332(8) 0.0198(17) Uani 1 1 d . . . H9 H 0.0281 0.2435 0.1049 0.024 Uiso 1 1 calc R . . C10 C 0.0967(3) 0.2289(6) 0.2348(8) 0.0208(16) Uani 1 1 d . . . H10 H 0.0922 0.3010 0.2802 0.025 Uiso 1 1 calc R . . C11 C 0.0187(3) 0.0445(6) -0.0363(8) 0.0192(16) Uani 1 1 d . . . H11A H 0.0377 0.0100 -0.1212 0.023 Uiso 1 1 calc R . . H11B H -0.0045 0.1081 -0.0738 0.023 Uiso 1 1 calc R . . O1W O 0.0000 0.485(5) 0.2500 0.38(6) Uani 0.50 2 d SP . . O2W O -0.007(3) 0.627(5) 0.187(5) 0.17(3) Uani 0.25 1 d P . . O3W O 0.0092(18) 0.549(4) 0.024(13) 0.27(6) Uani 0.25 1 d P . . O5W O 0.053(2) 0.655(7) 0.073(4) 0.24(4) Uani 0.25 1 d P . . 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 0.0116(4) 0.0161(4) 0.0171(5) 0.0007(4) -0.0023(3) -0.0024(4) N1 0.013(3) 0.025(4) 0.018(4) 0.002(3) -0.002(3) -0.001(2) O1 0.021(3) 0.016(3) 0.031(3) -0.001(2) -0.010(2) 0.003(2) O2 0.014(3) 0.020(3) 0.036(4) 0.003(2) -0.007(2) 0.000(2) O3 0.019(3) 0.038(3) 0.019(3) -0.003(3) 0.000(2) -0.008(2) O4 0.016(3) 0.025(3) 0.025(3) -0.002(2) 0.000(2) -0.0061(19) C1 0.019(4) 0.024(4) 0.008(4) 0.001(3) -0.001(3) 0.010(3) C2 0.024(4) 0.015(4) 0.026(5) -0.003(3) -0.006(3) 0.004(3) C3 0.020(4) 0.018(4) 0.029(5) 0.000(3) -0.003(3) -0.002(3) C4 0.025(4) 0.020(4) 0.024(5) 0.001(3) 0.003(3) -0.008(3) C5 0.025(4) 0.002(3) 0.026(4) 0.002(3) 0.002(3) -0.006(3) C6 0.011(4) 0.022(4) 0.028(5) 0.012(3) -0.005(3) -0.004(3) C7 0.017(4) 0.021(4) 0.018(4) 0.002(3) -0.003(3) -0.004(3) C8 0.009(3) 0.020(4) 0.019(4) 0.003(3) 0.002(3) -0.007(3) C9 0.012(4) 0.023(4) 0.025(5) 0.002(3) 0.001(3) 0.000(3) C10 0.022(4) 0.020(3) 0.020(4) -0.007(4) 0.001(3) -0.007(3) C11 0.016(4) 0.026(4) 0.015(4) 0.005(3) -0.005(3) -0.005(3) O1W 0.29(8) 0.21(5) 0.64(16) 0.000 0.38(10) 0.000 O2W 0.18(6) 0.20(5) 0.12(6) 0.04(4) -0.01(5) -0.10(5) O3W 0.05(3) 0.08(3) 0.67(17) -0.14(6) -0.06(6) -0.01(2) O5W 0.18(5) 0.50(11) 0.04(3) 0.09(5) 0.03(3) 0.20(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 O2 1.954(5) 6_565 ? Cu1 O1 1.956(5) 4_546 ? Cu1 O4 1.956(5) 7_556 ? Cu1 O3 1.963(5) . ? Cu1 N1 2.157(6) . ? Cu1 Cu1 2.6030(17) 7_556 ? N1 C6 1.318(9) . ? N1 C10 1.334(9) . ? O1 C1 1.256(8) . ? O1 Cu1 1.956(5) 4_556 ? O2 C1 1.240(8) . ? O2 Cu1 1.954(5) 6_566 ? O3 C5 1.249(9) . ? O4 C5 1.238(8) . ? O4 Cu1 1.956(5) 7_556 ? C1 C2 1.486(10) . ? C2 C3 1.510(10) . ? C3 C4 1.531(9) . ? C4 C5 1.498(10) . ? C6 C7 1.364(10) . ? C7 C8 1.393(9) . ? C8 C9 1.363(9) . ? C8 C11 1.496(9) . ? C9 C10 1.366(10) . ? C11 C11 1.536(13) 5 ? O1W O2W 1.77(7) 2 ? O1W O2W 1.77(7) . ? O2W O2W 1.19(9) 2 ? O2W O3W 1.80(10) . ? O3W O3W 1.30(8) 5_565 ? O3W O5W 1.69(10) . ? 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 O2 Cu1 O1 168.6(2) 6_565 4_546 ? O2 Cu1 O4 89.2(2) 6_565 7_556 ? O1 Cu1 O4 89.3(2) 4_546 7_556 ? O2 Cu1 O3 87.1(2) 6_565 . ? O1 Cu1 O3 92.0(2) 4_546 . ? O4 Cu1 O3 167.8(2) 7_556 . ? O2 Cu1 N1 98.9(2) 6_565 . ? O1 Cu1 N1 92.5(2) 4_546 . ? O4 Cu1 N1 93.4(2) 7_556 . ? O3 Cu1 N1 98.6(2) . . ? O2 Cu1 Cu1 88.99(14) 6_565 7_556 ? O1 Cu1 Cu1 79.57(14) 4_546 7_556 ? O4 Cu1 Cu1 81.78(15) 7_556 7_556 ? O3 Cu1 Cu1 86.54(15) . 7_556 ? N1 Cu1 Cu1 170.71(17) . 7_556 ? C6 N1 C10 116.9(6) . . ? C6 N1 Cu1 120.2(5) . . ? C10 N1 Cu1 122.9(5) . . ? C1 O1 Cu1 128.4(4) . 4_556 ? C1 O2 Cu1 117.8(5) . 6_566 ? C5 O3 Cu1 119.7(4) . . ? C5 O4 Cu1 125.5(5) . 7_556 ? O2 C1 O1 125.2(7) . . ? O2 C1 C2 119.9(7) . . ? O1 C1 C2 114.9(6) . . ? C1 C2 C3 116.2(6) . . ? C2 C3 C4 113.2(6) . . ? C5 C4 C3 108.9(6) . . ? O4 C5 O3 125.2(7) . . ? O4 C5 C4 117.0(7) . . ? O3 C5 C4 117.8(6) . . ? N1 C6 C7 123.9(7) . . ? C6 C7 C8 118.9(7) . . ? C9 C8 C7 117.1(6) . . ? C9 C8 C11 122.6(6) . . ? C7 C8 C11 120.3(6) . . ? C8 C9 C10 120.1(7) . . ? N1 C10 C9 122.9(7) . . ? C8 C11 C11 110.6(7) . 5 ? O2W O1W O2W 39(3) 2 . ? O2W O2W O1W 70.4(17) 2 . ? O2W O2W O3W 136(7) 2 . ? O1W O2W O3W 76(4) . . ? O3W O3W O5W 161(7) 5_565 . ? O3W O3W O2W 130(10) 5_565 . ? O5W O3W O2W 63(3) . . ? 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 C1 C2 C3 C4 162.3(6) . . . . ? C2 C3 C4 C5 -76.5(8) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.873 _refine_diff_density_min -0.725 _refine_diff_density_rms 0.134 data_compound2c _database_code_CSD 203226 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '(C22 H24 Cu2 N2 O8)n,5n(H2 O1)' _chemical_formula_sum 'C22 H24 Cu2 N2 O13' _chemical_formula_weight 651.51 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 C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.911(3) _cell_length_b 11.8685(15) _cell_length_c 9.2063(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.350(2) _cell_angle_gamma 90.00 _cell_volume 2612.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2902 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 24.97 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.656 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 1.698 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.8146 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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_% ? _diffrn_reflns_number 6627 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2292 _reflns_number_gt 1850 _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^)+(0.0325P)^2^+8.1693P] 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 2292 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.0948 _refine_ls_wR_factor_gt 0.0885 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.204990(18) 0.22769(4) 0.42146(5) 0.01741(15) Uani 1 1 d . . . N1 N 0.13981(12) 0.1669(3) 0.2759(3) 0.0192(7) Uani 1 1 d . . . O1 O 0.26512(11) 0.5752(2) 1.0457(3) 0.0237(6) Uani 1 1 d . . . O2 O 0.18801(11) 0.6105(2) 0.9153(3) 0.0279(7) Uani 1 1 d . . . O3 O 0.16414(11) 0.2261(2) 0.6076(3) 0.0280(6) Uani 1 1 d . . . O4 O 0.24189(11) 0.2505(2) 0.7387(3) 0.0266(7) Uani 1 1 d . . . C1 C 0.22126(16) 0.5449(3) 0.9794(4) 0.0199(8) Uani 1 1 d . . . C2 C 0.21030(17) 0.4202(3) 0.9753(5) 0.0253(9) Uani 1 1 d . . . H2A H 0.2107 0.3915 1.0762 0.030 Uiso 1 1 calc R . . H2B H 0.2415 0.3834 0.9233 0.030 Uiso 1 1 calc R . . C3 C 0.15557(16) 0.3841(3) 0.9035(4) 0.0240(9) Uani 1 1 d . . . H3A H 0.1491 0.4303 0.8155 0.029 Uiso 1 1 calc R . . H3B H 0.1244 0.3984 0.9712 0.029 Uiso 1 1 calc R . . C4 C 0.15562(17) 0.2582(3) 0.8607(4) 0.0259(9) Uani 1 1 d . . . H4A H 0.1716 0.2127 0.9410 0.031 Uiso 1 1 calc R . . H4B H 0.1168 0.2325 0.8429 0.031 Uiso 1 1 calc R . . C5 C 0.18979(16) 0.2423(3) 0.7260(5) 0.0230(9) Uani 1 1 d . . . C6 C 0.14393(15) 0.0641(3) 0.2176(4) 0.0201(8) Uani 1 1 d . . . H6 H 0.1739 0.0170 0.2479 0.024 Uiso 1 1 calc R . . C7 C 0.10673(15) 0.0232(3) 0.1157(4) 0.0217(8) Uani 1 1 d . . . H7 H 0.1119 -0.0497 0.0755 0.026 Uiso 1 1 calc R . . C8 C 0.06149(14) 0.0892(3) 0.0718(4) 0.0203(9) Uani 1 1 d . . . C9 C 0.05680(15) 0.1948(3) 0.1324(4) 0.0224(9) Uani 1 1 d . . . H9 H 0.0267 0.2429 0.1054 0.027 Uiso 1 1 calc R . . C10 C 0.09615(15) 0.2303(3) 0.2330(4) 0.0221(8) Uani 1 1 d . . . H10 H 0.0921 0.3033 0.2739 0.027 Uiso 1 1 calc R . . C11 C 0.01901(15) 0.0444(3) -0.0351(5) 0.0246(9) Uani 1 1 d . . . H11A H 0.0386 0.0104 -0.1187 0.030 Uiso 1 1 calc R . . H11B H -0.0042 0.1075 -0.0719 0.030 Uiso 1 1 calc R . . O1W O 0.9881(3) 0.4323(7) 0.0809(10) 0.0650(17) Uiso 0.505(9) 1 d P . . O2W O 0.9396(5) 0.3727(14) -0.050(2) 0.0650(17) Uiso 0.402(18) 1 d P . . O3W O 0.9428(6) 0.3069(14) -0.1244(18) 0.0650(17) Uiso 0.272(9) 1 d P . . O4W O 0.9753(6) 0.5280(12) 0.1750(17) 0.0650(17) Uiso 0.295(8) 1 d P . . O5W O 1.0000 0.4907(18) 0.2500 0.0650(17) Uiso 0.289(12) 2 d SP . . O6W O 0.9586(8) 0.4108(17) -0.159(2) 0.0650(17) Uiso 0.204(8) 1 d P . . O7W O 0.9856(9) 0.4652(18) -0.042(3) 0.0650(17) Uiso 0.181(8) 1 d P . . O8W O 0.9453(10) 0.402(2) 0.011(4) 0.0650(17) Uiso 0.199(18) 1 d P . . O9W O 1.0000 0.342(2) -0.2500 0.0650(17) Uiso 0.194(10) 2 d SP . . 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 0.0170(2) 0.0157(2) 0.0195(3) -0.0006(2) -0.00272(17) -0.00280(19) N1 0.0162(16) 0.0206(18) 0.0208(18) -0.0013(13) -0.0018(13) -0.0041(13) O1 0.0241(15) 0.0186(14) 0.0285(16) -0.0010(12) -0.0067(12) 0.0014(11) O2 0.0283(15) 0.0177(14) 0.0375(18) 0.0031(12) -0.0117(13) 0.0001(11) O3 0.0226(14) 0.0336(15) 0.0278(16) -0.0098(13) 0.0023(12) -0.0076(12) O4 0.0232(15) 0.0383(18) 0.0182(14) 0.0050(12) 0.0006(11) -0.0052(12) C1 0.023(2) 0.022(2) 0.014(2) -0.0002(16) 0.0013(16) 0.0010(16) C2 0.031(2) 0.016(2) 0.030(2) -0.0020(17) -0.0051(18) -0.0001(16) C3 0.026(2) 0.021(2) 0.025(2) -0.0013(17) 0.0034(17) -0.0032(16) C4 0.031(2) 0.022(2) 0.025(2) -0.0012(17) 0.0071(18) -0.0098(17) C5 0.027(2) 0.012(2) 0.030(2) -0.0014(16) 0.0000(18) -0.0068(15) C6 0.0165(19) 0.018(2) 0.026(2) 0.0008(16) -0.0030(16) 0.0005(15) C7 0.023(2) 0.020(2) 0.022(2) -0.0048(17) -0.0010(17) -0.0025(16) C8 0.0146(18) 0.027(2) 0.019(2) 0.0017(16) 0.0010(16) -0.0086(15) C9 0.0150(18) 0.029(2) 0.024(2) 0.0042(17) 0.0007(16) -0.0002(15) C10 0.0193(19) 0.0197(18) 0.027(2) -0.0037(17) -0.0018(16) -0.0053(16) C11 0.0188(19) 0.032(2) 0.023(2) 0.0010(18) -0.0029(16) -0.0065(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 Cu1 O2 1.963(3) 6_565 ? Cu1 O1 1.968(3) 4_546 ? Cu1 O4 1.969(3) 7_556 ? Cu1 O3 1.978(3) . ? Cu1 N1 2.172(3) . ? Cu1 Cu1 2.6394(9) 7_556 ? N1 C6 1.337(5) . ? N1 C10 1.344(5) . ? O1 C1 1.263(4) . ? O1 Cu1 1.968(3) 4_556 ? O2 C1 1.258(4) . ? O2 Cu1 1.963(3) 6_566 ? O3 C5 1.262(5) . ? O4 C5 1.254(5) . ? O4 Cu1 1.969(3) 7_556 ? C1 C2 1.503(5) . ? C2 C3 1.524(5) . ? C3 C4 1.545(5) . ? C4 C5 1.502(5) . ? C6 C7 1.377(5) . ? C7 C8 1.393(5) . ? C8 C9 1.377(5) . ? C8 C11 1.506(5) . ? C9 C10 1.382(5) . ? C11 C11 1.537(7) 5 ? O1W O7W 1.20(2) . ? O1W O8W 1.26(3) . ? O1W O7W 1.42(2) 5_765 ? O1W O4W 1.462(15) . ? O1W O5W 1.726(12) . ? O1W O2W 1.81(2) . ? O2W O8W 0.67(3) . ? O2W O3W 1.04(2) . ? O2W O6W 1.19(2) . ? O2W O7W 1.55(3) . ? O3W O6W 1.33(2) . ? O3W O8W 1.68(4) . ? O4W O5W 1.008(16) . ? O4W O7W 1.55(3) 5_765 ? O4W O6W 1.74(3) 6_566 ? O4W O6W 1.75(2) 5_765 ? O4W O9W 1.79(3) 5_765 ? O4W O4W 1.81(3) 2_755 ? O5W O4W 1.008(16) 2_755 ? O5W O1W 1.726(12) 2_755 ? O5W O6W 1.75(3) 5_765 ? O5W O6W 1.75(3) 6_566 ? O6W O7W 1.41(3) . ? O6W O9W 1.54(2) . ? O6W O8W 1.60(4) . ? O6W O4W 1.74(3) 6_565 ? O6W O4W 1.75(2) 5_765 ? O6W O5W 1.75(3) 5_765 ? O7W O8W 1.32(3) . ? O7W O7W 1.32(4) 5_765 ? O7W O1W 1.42(2) 5_765 ? O7W O4W 1.55(3) 5_765 ? O9W O6W 1.54(2) 2_754 ? O9W O4W 1.79(3) 5_765 ? O9W O4W 1.79(3) 6_565 ? 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 O2 Cu1 O1 168.08(11) 6_565 4_546 ? O2 Cu1 O4 89.07(12) 6_565 7_556 ? O1 Cu1 O4 90.04(11) 4_546 7_556 ? O2 Cu1 O3 86.05(12) 6_565 . ? O1 Cu1 O3 92.25(12) 4_546 . ? O4 Cu1 O3 166.99(11) 7_556 . ? O2 Cu1 N1 99.17(11) 6_565 . ? O1 Cu1 N1 92.74(11) 4_546 . ? O4 Cu1 N1 92.60(11) 7_556 . ? O3 Cu1 N1 100.08(11) . . ? O2 Cu1 Cu1 89.29(8) 6_565 7_556 ? O1 Cu1 Cu1 78.82(8) 4_546 7_556 ? O4 Cu1 Cu1 81.74(8) 7_556 7_556 ? O3 Cu1 Cu1 86.14(8) . 7_556 ? N1 Cu1 Cu1 169.78(9) . 7_556 ? C6 N1 C10 116.8(3) . . ? C6 N1 Cu1 119.8(2) . . ? C10 N1 Cu1 123.3(2) . . ? C1 O1 Cu1 129.5(2) . 4_556 ? C1 O2 Cu1 117.5(2) . 6_566 ? C5 O3 Cu1 120.4(2) . . ? C5 O4 Cu1 125.8(3) . 7_556 ? O2 C1 O1 124.8(3) . . ? O2 C1 C2 119.2(3) . . ? O1 C1 C2 115.9(3) . . ? C1 C2 C3 115.9(3) . . ? C2 C3 C4 112.4(3) . . ? C5 C4 C3 109.5(3) . . ? O4 C5 O3 124.7(4) . . ? O4 C5 C4 117.3(4) . . ? O3 C5 C4 117.9(3) . . ? N1 C6 C7 123.1(3) . . ? C6 C7 C8 119.8(3) . . ? C9 C8 C7 117.3(3) . . ? C9 C8 C11 122.0(3) . . ? C7 C8 C11 120.7(3) . . ? C8 C9 C10 119.5(4) . . ? N1 C10 C9 123.4(4) . . ? C8 C11 C11 111.5(4) . 5 ? O7W O1W O8W 65.0(15) . . ? O7W O1W O7W 59.9(18) . 5_765 ? O8W O1W O7W 118.6(17) . 5_765 ? O7W O1W O4W 107.3(14) . . ? O8W O1W O4W 110.8(17) . . ? O7W O1W O4W 65.1(11) 5_765 . ? O7W O1W O5W 136.7(14) . . ? O8W O1W O5W 134.9(17) . . ? O7W O1W O5W 79.3(12) 5_765 . ? O4W O1W O5W 35.7(7) . . ? O7W O1W O2W 58.1(12) . . ? O8W O1W O2W 14.6(14) . . ? O7W O1W O2W 116.7(13) 5_765 . ? O4W O1W O2W 124.2(10) . . ? O5W O1W O2W 149.1(7) . . ? O8W O2W O3W 157(3) . . ? O8W O2W O6W 116(3) . . ? O3W O2W O6W 72.5(18) . . ? O8W O2W O7W 57(3) . . ? O3W O2W O7W 120.3(17) . . ? O6W O2W O7W 60.1(14) . . ? O8W O2W O1W 28(2) . . ? O3W O2W O1W 132.9(13) . . ? O6W O2W O1W 99.6(14) . . ? O7W O2W O1W 40.8(10) . . ? O2W O3W O6W 59.0(13) . . ? O2W O3W O8W 9.1(13) . . ? O6W O3W O8W 63.1(15) . . ? O5W O4W O1W 86.6(13) . . ? O5W O4W O7W 102.2(14) . 5_765 ? O1W O4W O7W 56.1(10) . 5_765 ? O5W O4W O6W 73.7(14) . 6_566 ? O1W O4W O6W 153.4(13) . 6_566 ? O7W O4W O6W 144.8(14) 5_765 6_566 ? O5W O4W O6W 73.4(14) . 5_765 ? O1W O4W O6W 94.6(10) . 5_765 ? O7W O4W O6W 50.2(11) 5_765 5_765 ? O6W O4W O6W 96.6(13) 6_566 5_765 ? O5W O4W O9W 85.6(17) . 5_765 ? O1W O4W O9W 146.0(10) . 5_765 ? O7W O4W O9W 93.5(10) 5_765 5_765 ? O6W O4W O9W 51.6(8) 6_566 5_765 ? O6W O4W O9W 51.5(8) 5_765 5_765 ? O5W O4W O4W 26.1(15) . 2_755 ? O1W O4W O4W 108.3(9) . 2_755 ? O7W O4W O4W 102.1(14) 5_765 2_755 ? O6W O4W O4W 58.9(10) 6_566 2_755 ? O6W O4W O4W 58.6(10) 5_765 2_755 ? O9W O4W O4W 59.6(7) 5_765 2_755 ? O4W O5W O4W 128(3) 2_755 . ? O4W O5W O1W 152.5(9) 2_755 . ? O4W O5W O1W 57.7(10) . . ? O4W O5W O1W 57.7(10) 2_755 2_755 ? O4W O5W O1W 152.5(9) . 2_755 ? O1W O5W O1W 132.7(14) . 2_755 ? O4W O5W O6W 72.8(14) 2_755 5_765 ? O4W O5W O6W 73.1(14) . 5_765 ? O1W O5W O6W 85.8(7) . 5_765 ? O1W O5W O6W 127.6(8) 2_755 5_765 ? O4W O5W O6W 73.1(14) 2_755 6_566 ? O4W O5W O6W 72.8(14) . 6_566 ? O1W O5W O6W 127.6(8) . 6_566 ? O1W O5W O6W 85.8(7) 2_755 6_566 ? O6W O5W O6W 96.2(17) 5_765 6_566 ? O2W O6W O3W 48.5(13) . . ? O2W O6W O7W 72.8(18) . . ? O3W O6W O7W 112(2) . . ? O2W O6W O9W 120.5(19) . . ? O3W O6W O9W 79.7(15) . . ? O7W O6W O9W 111.5(17) . . ? O2W O6W O8W 22.2(11) . . ? O3W O6W O8W 69.3(17) . . ? O7W O6W O8W 51.4(16) . . ? O9W O6W O8W 129.0(16) . . ? O2W O6W O4W 171.0(18) . 6_565 ? O3W O6W O4W 131.5(17) . 6_565 ? O7W O6W O4W 112.0(17) . 6_565 ? O9W O6W O4W 65.7(13) . 6_565 ? O8W O6W O4W 159.0(18) . 6_565 ? O2W O6W O4W 125.3(18) . 5_765 ? O3W O6W O4W 131.6(16) . 5_765 ? O7W O6W O4W 57.6(13) . 5_765 ? O9W O6W O4W 65.6(12) . 5_765 ? O8W O6W O4W 107.2(17) . 5_765 ? O4W O6W O4W 62.5(12) 6_565 5_765 ? O2W O6W O5W 151(2) . 5_765 ? O3W O6W O5W 153.7(18) . 5_765 ? O7W O6W O5W 78.6(14) . 5_765 ? O9W O6W O5W 73.9(14) . 5_765 ? O8W O6W O5W 129.0(18) . 5_765 ? O4W O6W O5W 33.6(6) 6_565 5_765 ? O4W O6W O5W 33.5(6) 5_765 5_765 ? O1W O7W O8W 60(2) . . ? O1W O7W O7W 68(2) . 5_765 ? O8W O7W O7W 122(4) . 5_765 ? O1W O7W O6W 126(2) . . ? O8W O7W O6W 72(2) . . ? O7W O7W O6W 165(3) 5_765 . ? O1W O7W O1W 120.1(18) . 5_765 ? O8W O7W O1W 156(2) . 5_765 ? O7W O7W O1W 51.6(16) 5_765 5_765 ? O6W O7W O1W 114(2) . 5_765 ? O1W O7W O4W 137.6(19) . 5_765 ? O8W O7W O4W 140(3) . 5_765 ? O7W O7W O4W 96(2) 5_765 5_765 ? O6W O7W O4W 72.2(15) . 5_765 ? O1W O7W O4W 58.8(11) 5_765 5_765 ? O1W O7W O2W 81.1(16) . . ? O8W O7W O2W 25.4(15) . . ? O7W O7W O2W 147(3) 5_765 . ? O6W O7W O2W 47.1(12) . . ? O1W O7W O2W 155(2) 5_765 . ? O4W O7W O2W 115.4(17) 5_765 . ? O2W O8W O1W 137(3) . . ? O2W O8W O7W 97(3) . . ? O1W O8W O7W 55.3(16) . . ? O2W O8W O6W 42(2) . . ? O1W O8W O6W 108.3(18) . . ? O7W O8W O6W 56.7(17) . . ? O2W O8W O3W 14(2) . . ? O1W O8W O3W 126.7(19) . . ? O7W O8W O3W 97(2) . . ? O6W O8W O3W 47.6(14) . . ? O6W O9W O6W 116(2) . 2_754 ? O6W O9W O4W 62.9(13) . 5_765 ? O6W O9W O4W 62.7(13) 2_754 5_765 ? O6W O9W O4W 62.7(13) . 6_565 ? O6W O9W O4W 62.9(13) 2_754 6_565 ? O4W O9W O4W 60.9(14) 5_765 6_565 ? 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 C2 C3 C4 C5 -76.5(4) . . . . ? C1 C2 C3 C4 162.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.525 _refine_diff_density_min -0.476 _refine_diff_density_rms 0.086