Electronic Supplementary Material for CrystEngComm This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 1350 _publ_requested_journal ' CrystEngComm ' _publ_contact_author_name ' Paul E. Kruger ' _publ_contact_author_address ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; _publ_contact_author_phone ' 353 1 608 1422 ' _publ_contact_author_fax ' 353 1 671 2826 ' _publ_contact_author_email ' paul.kruger@tcd.ie ' loop_ _publ_author_name _publ_author_address 'Paul E. Kruger' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; 'Eithne Tynan' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; 'Anthea C. Lees' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; 'Paul Jensen' ; Department of Chemistry Trinity College Dublin Dublin 2 Ireland ; 'Keith S. Murray' ; School of Chemistry Monash University Clayton, Victoria 3800 Australia ; 'Boujemaa Moubaraki' ; School of Chemistry Monash University Clayton, Victoria 3800 Australia ; _publ_section_title ; The role of acid in the formation of hydrogen-bonded networks featuring 4,4'-dicarboxy-2,2'-bipyridine (H2dcbp): Synthesis, structural and magnetic characterisation of {[Cu(H2dcbp)Cl2].H2O}2 and [Cu(H2dcbp)(NO3)2(H2O)] ; data_1 _database_code_depnum_ccdc_archive 'CCDC 256268' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Cu2(H2dcbp)2Cl4.2H2O _chemical_formula_sum 'C12 H10 Cl2 Cu N2 O5' _chemical_formula_weight 396.66 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2504(16) _cell_length_b 9.346(2) _cell_length_c 11.785(3) _cell_angle_alpha 108.400(3) _cell_angle_beta 98.483(3) _cell_angle_gamma 108.720(3) _cell_volume 689.6(3) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.910 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 398 _exptl_absorpt_coefficient_mu 1.996 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.570 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Bruker SMART APEX CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7458 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_sigmaI/netI 0.0326 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.98 _reflns_number_total 2962 _reflns_number_gt 2725 _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^)+(0.0606P)^2^+0.0524P] 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 2962 _refine_ls_number_parameters 215 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0337 _refine_ls_wR_factor_ref 0.0947 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.096 _refine_ls_restrained_S_all 1.096 _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 -0.18956(4) 0.07006(3) -0.02212(2) 0.01634(12) Uani 1 1 d . . . Cl1 Cl 0.07633(8) -0.00823(7) -0.14048(5) 0.01907(15) Uani 1 1 d . . . Cl2 Cl 0.01301(9) 0.33602(6) 0.08275(5) 0.02205(15) Uani 1 1 d . . . O1 O -0.8067(3) 0.03031(19) -0.55713(17) 0.0232(4) Uani 1 1 d . . . O2 O -0.5968(3) 0.2945(2) -0.47512(17) 0.0256(4) Uani 1 1 d D . . O3 O -1.0493(3) -0.6182(2) -0.41494(16) 0.0260(4) Uani 1 1 d . . . O4 O -0.9039(3) -0.7345(2) -0.30981(18) 0.0245(4) Uani 1 1 d D . . O5 O -0.7864(3) 0.3540(2) -0.64035(19) 0.0368(5) Uani 1 1 d D . . N1 N -0.3382(3) 0.1091(2) -0.16143(18) 0.0164(4) Uani 1 1 d . . . N2 N -0.4170(3) -0.1554(2) -0.11508(18) 0.0168(4) Uani 1 1 d . . . C1 C -0.2889(4) 0.2522(3) -0.1749(2) 0.0205(5) Uani 1 1 d . . . H1 H -0.1788 0.3454 -0.1137 0.025 Uiso 1 1 calc R . . C2 C -0.3929(4) 0.2696(3) -0.2751(2) 0.0197(5) Uani 1 1 d . . . H2 H -0.3551 0.3730 -0.2820 0.024 Uiso 1 1 calc R . . C3 C -0.5528(3) 0.1339(3) -0.3648(2) 0.0165(5) Uani 1 1 d . . . C4 C -0.6058(3) -0.0155(3) -0.3505(2) 0.0172(5) Uani 1 1 d . . . H4 H -0.7154 -0.1102 -0.4105 0.021 Uiso 1 1 calc R . . C5 C -0.4964(3) -0.0235(3) -0.2476(2) 0.0158(5) Uani 1 1 d . . . C6 C -0.5403(3) -0.1738(3) -0.2213(2) 0.0156(4) Uani 1 1 d . . . C7 C -0.6981(3) -0.3216(3) -0.2965(2) 0.0179(5) Uani 1 1 d . . . H7 H -0.7822 -0.3321 -0.3711 0.021 Uiso 1 1 calc R . . C8 C -0.7317(3) -0.4538(3) -0.2616(2) 0.0172(5) Uani 1 1 d . . . C9 C -0.6033(4) -0.4357(3) -0.1531(2) 0.0202(5) Uani 1 1 d . . . H9 H -0.6224 -0.5250 -0.1276 0.024 Uiso 1 1 calc R . . C10 C -0.4479(4) -0.2852(3) -0.0833(2) 0.0210(5) Uani 1 1 d . . . H10 H -0.3592 -0.2730 -0.0098 0.025 Uiso 1 1 calc R . . C11 C -0.6667(3) 0.1455(3) -0.4757(2) 0.0180(5) Uani 1 1 d . . . C12 C -0.9111(4) -0.6096(3) -0.3376(2) 0.0193(5) Uani 1 1 d . . . H2A H -0.664(4) 0.306(4) -0.533(2) 0.039(9) Uiso 1 1 d D . . H4A H -1.006(3) -0.819(2) -0.351(3) 0.037(9) Uiso 1 1 d D . . H5A H -0.835(6) 0.425(4) -0.628(4) 0.079(15) Uiso 1 1 d D . . H5B H -0.856(4) 0.294(3) -0.7130(14) 0.043(10) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01507(17) 0.01082(16) 0.01677(18) 0.00278(12) -0.00143(11) 0.00229(12) Cl1 0.0202(3) 0.0161(3) 0.0165(3) 0.0049(2) 0.0007(2) 0.0050(2) Cl2 0.0223(3) 0.0120(3) 0.0218(3) 0.0020(2) -0.0028(2) 0.0024(2) O1 0.0240(9) 0.0127(8) 0.0225(9) 0.0044(7) -0.0035(7) 0.0009(7) O2 0.0302(10) 0.0130(8) 0.0237(10) 0.0080(7) -0.0048(7) 0.0005(7) O3 0.0260(9) 0.0168(8) 0.0245(10) 0.0072(7) -0.0050(7) 0.0014(7) O4 0.0210(9) 0.0120(8) 0.0325(10) 0.0084(8) -0.0021(8) 0.0008(7) O5 0.0479(13) 0.0228(10) 0.0252(11) 0.0033(8) -0.0129(9) 0.0120(10) N1 0.0155(9) 0.0119(9) 0.0171(10) 0.0036(8) 0.0010(7) 0.0033(8) N2 0.0145(9) 0.0132(9) 0.0191(10) 0.0052(8) 0.0006(7) 0.0037(7) C1 0.0166(11) 0.0118(10) 0.0234(13) 0.0032(9) -0.0016(9) 0.0005(9) C2 0.0209(12) 0.0101(10) 0.0218(12) 0.0049(9) 0.0010(9) 0.0019(9) C3 0.0154(11) 0.0147(10) 0.0169(12) 0.0043(9) 0.0030(9) 0.0051(9) C4 0.0159(11) 0.0116(10) 0.0187(12) 0.0035(9) 0.0013(9) 0.0028(9) C5 0.0136(11) 0.0115(10) 0.0192(12) 0.0037(9) 0.0029(8) 0.0040(9) C6 0.0155(11) 0.0125(10) 0.0163(11) 0.0047(9) 0.0028(8) 0.0040(9) C7 0.0163(11) 0.0137(10) 0.0170(12) 0.0034(9) -0.0004(9) 0.0024(9) C8 0.0153(11) 0.0128(10) 0.0195(12) 0.0037(9) 0.0025(9) 0.0042(9) C9 0.0188(12) 0.0159(10) 0.0240(13) 0.0083(10) 0.0020(9) 0.0057(9) C10 0.0181(12) 0.0187(11) 0.0241(13) 0.0093(10) 0.0002(9) 0.0062(10) C11 0.0176(11) 0.0143(10) 0.0204(12) 0.0058(9) 0.0035(9) 0.0058(9) C12 0.0209(12) 0.0140(10) 0.0194(12) 0.0045(9) 0.0051(9) 0.0044(9) _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 N1 2.0243(19) . ? Cu1 N2 2.0345(19) . ? Cu1 Cl2 2.2460(7) . ? Cu1 Cl1 2.2846(7) 2 ? Cu1 Cl1 2.6930(8) . ? Cl1 Cu1 2.2846(7) 2 ? O1 C11 1.212(3) . ? O2 C11 1.317(3) . ? O3 C12 1.214(3) . ? O4 C12 1.322(3) . ? N1 C1 1.337(3) . ? N1 C5 1.353(3) . ? N2 C10 1.341(3) . ? N2 C6 1.353(3) . ? C1 C2 1.388(3) . ? C2 C3 1.385(3) . ? C3 C4 1.396(3) . ? C3 C11 1.494(3) . ? C4 C5 1.385(3) . ? C5 C6 1.479(3) . ? C6 C7 1.384(3) . ? C7 C8 1.383(3) . ? C8 C9 1.394(3) . ? C8 C12 1.494(3) . ? C9 C10 1.380(3) . ? 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 N1 Cu1 N2 79.76(7) . . ? N1 Cu1 Cl2 94.03(6) . . ? N2 Cu1 Cl2 168.99(6) . . ? N1 Cu1 Cl1 169.96(6) . 2 ? N2 Cu1 Cl1 93.85(6) . 2 ? Cl2 Cu1 Cl1 90.98(3) . 2 ? N1 Cu1 Cl1 95.33(6) . . ? N2 Cu1 Cl1 94.20(6) . . ? Cl2 Cu1 Cl1 95.44(3) . . ? Cl1 Cu1 Cl1 92.84(2) 2 . ? Cu1 Cl1 Cu1 87.16(2) 2 . ? C1 N1 C5 119.08(19) . . ? C1 N1 Cu1 125.12(15) . . ? C5 N1 Cu1 115.78(15) . . ? C10 N2 C6 118.69(19) . . ? C10 N2 Cu1 126.06(16) . . ? C6 N2 Cu1 115.18(15) . . ? N1 C1 C2 122.3(2) . . ? C3 C2 C1 119.1(2) . . ? C2 C3 C4 118.8(2) . . ? C2 C3 C11 121.1(2) . . ? C4 C3 C11 120.10(19) . . ? C5 C4 C3 119.0(2) . . ? N1 C5 C4 121.7(2) . . ? N1 C5 C6 114.31(19) . . ? C4 C5 C6 124.0(2) . . ? N2 C6 C7 121.9(2) . . ? N2 C6 C5 114.76(18) . . ? C7 C6 C5 123.4(2) . . ? C8 C7 C6 119.1(2) . . ? C7 C8 C9 119.1(2) . . ? C7 C8 C12 119.1(2) . . ? C9 C8 C12 121.7(2) . . ? C10 C9 C8 118.6(2) . . ? N2 C10 C9 122.6(2) . . ? O1 C11 O2 124.1(2) . . ? O1 C11 C3 123.6(2) . . ? O2 C11 C3 112.32(19) . . ? O3 C12 O4 124.2(2) . . ? O3 C12 C8 122.9(2) . . ? O4 C12 C8 112.84(19) . . ? _diffrn_measured_fraction_theta_max 0.889 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.889 _refine_diff_density_max 0.814 _refine_diff_density_min -0.656 _refine_diff_density_rms 0.101 data_2 _database_code_depnum_ccdc_archive 'CCDC 256269' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety Cu(H2dcbp)(NO3)2(H2O) _chemical_formula_sum 'C12 H10 Cu N4 O11' _chemical_formula_weight 449.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.4404(4) _cell_length_b 9.7045(6) _cell_length_c 13.6309(8) _cell_angle_alpha 76.3390(10) _cell_angle_beta 84.2050(10) _cell_angle_gamma 78.8940(10) _cell_volume 810.96(9) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 454 _exptl_absorpt_coefficient_mu 1.421 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.770 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Bruker SMART APEX CCD' _diffrn_measurement_method 'Omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8948 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 29.98 _reflns_number_total 4456 _reflns_number_gt 3899 _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^)+(0.0617P)^2^+1.0008P] 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 4456 _refine_ls_number_parameters 261 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0547 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.059 _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 0.19905(5) 0.87689(3) 0.28824(2) 0.01801(11) Uani 1 1 d . . . O10 O 0.0800(3) 1.0835(2) 0.23884(16) 0.0253(4) Uani 1 1 d . . . O11 O 0.4112(3) 0.9300(2) 0.36183(16) 0.0249(4) Uani 1 1 d D . . O2 O -0.5295(3) 0.6666(2) 0.03834(16) 0.0279(5) Uani 1 1 d . . . H2A H -0.5898 0.6175 0.0107 0.042 Uiso 1 1 calc R . . N1 N 0.0178(4) 0.8026(2) 0.21049(17) 0.0195(4) Uani 1 1 d . . . N2 N 0.3493(4) 0.6741(2) 0.31125(17) 0.0180(4) Uani 1 1 d . . . O9 O 0.1597(4) 1.2646(2) 0.12312(17) 0.0300(5) Uani 1 1 d . . . O3 O 0.5814(3) 0.1658(2) 0.27802(16) 0.0247(4) Uani 1 1 d . . . O4 O 0.7627(3) 0.1810(2) 0.40681(16) 0.0271(4) Uani 1 1 d . . . H4A H 0.8113 0.0939 0.4077 0.041 Uiso 1 1 calc R . . O7 O -0.0448(3) 0.9157(2) 0.41169(15) 0.0236(4) Uani 1 1 d . . . N3 N -0.1291(4) 0.8147(3) 0.47150(18) 0.0223(5) Uani 1 1 d . . . O1 O -0.2660(4) 0.4747(2) 0.04901(18) 0.0296(5) Uani 1 1 d . . . O8 O 0.3381(4) 1.0483(2) 0.12779(18) 0.0350(5) Uani 1 1 d . . . N4 N 0.1956(4) 1.1345(3) 0.16048(18) 0.0229(5) Uani 1 1 d . . . O6 O -0.2675(4) 0.8481(3) 0.53546(18) 0.0337(5) Uani 1 1 d . . . C12 C 0.6296(4) 0.2325(3) 0.3346(2) 0.0203(5) Uani 1 1 d . . . C11 C -0.3440(4) 0.5975(3) 0.0620(2) 0.0208(5) Uani 1 1 d . . . C8 C 0.5352(4) 0.3883(3) 0.3278(2) 0.0185(5) Uani 1 1 d . . . C6 C 0.2670(4) 0.5886(3) 0.26615(19) 0.0175(5) Uani 1 1 d . . . C1 C -0.1553(5) 0.8784(3) 0.1631(2) 0.0233(6) Uani 1 1 d . . . H1 H -0.1959 0.9775 0.1641 0.028 Uiso 1 1 calc R . . C4 C -0.0372(4) 0.5923(3) 0.1611(2) 0.0197(5) Uani 1 1 d . . . H4 H 0.0063 0.4930 0.1611 0.024 Uiso 1 1 calc R . . C5 C 0.0760(4) 0.6616(3) 0.20984(19) 0.0177(5) Uani 1 1 d . . . O5 O -0.0670(4) 0.6893(2) 0.4635(2) 0.0381(6) Uani 1 1 d . . . C10 C 0.5207(5) 0.6181(3) 0.3650(2) 0.0221(5) Uani 1 1 d . . . H10 H 0.5767 0.6783 0.3975 0.027 Uiso 1 1 calc R . . C7 C 0.3556(4) 0.4458(3) 0.2727(2) 0.0188(5) Uani 1 1 d . . . H7 H 0.2954 0.3877 0.2402 0.023 Uiso 1 1 calc R . . C9 C 0.6200(4) 0.4753(3) 0.3750(2) 0.0216(5) Uani 1 1 d . . . H9 H 0.7422 0.4383 0.4130 0.026 Uiso 1 1 calc R . . C3 C -0.2164(4) 0.6719(3) 0.1122(2) 0.0191(5) Uani 1 1 d . . . C2 C -0.2757(5) 0.8170(3) 0.1133(2) 0.0230(6) Uani 1 1 d . . . H2 H -0.3974 0.8728 0.0803 0.028 Uiso 1 1 calc R . . H11B H 0.353(5) 0.961(4) 0.4123(18) 0.031(10) Uiso 1 1 d D . . H11A H 0.479(6) 0.993(3) 0.328(3) 0.041(11) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02138(18) 0.01185(16) 0.02123(18) -0.00501(12) -0.00299(12) -0.00139(12) O10 0.0288(11) 0.0180(9) 0.0266(10) -0.0041(8) 0.0041(8) -0.0018(8) O11 0.0284(11) 0.0200(10) 0.0290(11) -0.0077(8) -0.0023(9) -0.0074(8) O2 0.0197(10) 0.0342(12) 0.0327(11) -0.0140(9) -0.0052(8) -0.0017(9) N1 0.0207(11) 0.0158(10) 0.0212(11) -0.0054(8) -0.0037(8) 0.0012(8) N2 0.0203(11) 0.0145(10) 0.0194(10) -0.0044(8) -0.0026(8) -0.0021(8) O9 0.0414(13) 0.0147(9) 0.0299(11) -0.0004(8) -0.0024(9) -0.0005(9) O3 0.0253(10) 0.0185(9) 0.0320(11) -0.0088(8) -0.0052(8) -0.0020(8) O4 0.0297(11) 0.0199(10) 0.0302(11) -0.0068(8) -0.0108(9) 0.0058(8) O7 0.0263(10) 0.0162(9) 0.0256(10) -0.0027(8) 0.0014(8) -0.0007(8) N3 0.0224(11) 0.0216(11) 0.0244(11) -0.0069(9) -0.0012(9) -0.0054(9) O1 0.0303(11) 0.0224(10) 0.0388(12) -0.0113(9) -0.0107(9) -0.0008(9) O8 0.0420(13) 0.0246(11) 0.0325(12) -0.0077(9) 0.0081(10) 0.0047(10) N4 0.0282(12) 0.0174(11) 0.0227(11) -0.0049(9) -0.0046(9) -0.0008(9) O6 0.0333(12) 0.0315(12) 0.0374(12) -0.0130(10) 0.0137(10) -0.0094(10) C12 0.0194(12) 0.0162(12) 0.0243(13) -0.0034(10) 0.0011(10) -0.0030(10) C11 0.0192(12) 0.0219(13) 0.0213(12) -0.0049(10) -0.0028(10) -0.0030(10) C8 0.0177(12) 0.0159(12) 0.0211(12) -0.0034(9) -0.0006(9) -0.0020(9) C6 0.0194(12) 0.0153(11) 0.0174(11) -0.0029(9) -0.0016(9) -0.0031(9) C1 0.0276(14) 0.0153(12) 0.0262(13) -0.0067(10) -0.0058(11) 0.0032(10) C4 0.0213(13) 0.0158(11) 0.0214(12) -0.0047(10) -0.0017(10) -0.0006(10) C5 0.0186(12) 0.0151(11) 0.0177(11) -0.0033(9) -0.0015(9) 0.0011(9) O5 0.0450(14) 0.0198(11) 0.0509(15) -0.0132(10) 0.0051(12) -0.0064(10) C10 0.0249(14) 0.0182(12) 0.0251(13) -0.0061(10) -0.0049(10) -0.0047(10) C7 0.0213(13) 0.0150(11) 0.0211(12) -0.0062(9) -0.0030(10) -0.0020(10) C9 0.0226(13) 0.0173(12) 0.0244(13) -0.0033(10) -0.0052(10) -0.0023(10) C3 0.0182(12) 0.0199(12) 0.0195(12) -0.0061(10) -0.0008(9) -0.0022(10) C2 0.0222(13) 0.0199(13) 0.0257(13) -0.0066(11) -0.0056(10) 0.0033(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 O11 1.983(2) . ? Cu1 O10 1.984(2) . ? Cu1 N1 1.985(2) . ? Cu1 N2 1.986(2) . ? Cu1 O7 2.231(2) . ? O10 N4 1.293(3) . ? O2 C11 1.284(3) . ? N1 C1 1.344(3) . ? N1 C5 1.349(3) . ? N2 C10 1.339(3) . ? N2 C6 1.351(3) . ? O9 N4 1.230(3) . ? O3 C12 1.213(3) . ? O4 C12 1.314(3) . ? O7 N3 1.287(3) . ? N3 O5 1.232(3) . ? N3 O6 1.235(3) . ? O1 C11 1.247(3) . ? O8 N4 1.240(3) . ? C12 C8 1.502(4) . ? C11 C3 1.497(4) . ? C8 C9 1.389(4) . ? C8 C7 1.394(4) . ? C6 C7 1.378(4) . ? C6 C5 1.484(4) . ? C1 C2 1.376(4) . ? C4 C5 1.387(4) . ? C4 C3 1.394(4) . ? C10 C9 1.391(4) . ? C3 C2 1.389(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 O11 Cu1 O10 90.23(9) . . ? O11 Cu1 N1 172.21(9) . . ? O10 Cu1 N1 95.94(9) . . ? O11 Cu1 N2 91.25(9) . . ? O10 Cu1 N2 168.69(9) . . ? N1 Cu1 N2 81.78(9) . . ? O11 Cu1 O7 89.41(9) . . ? O10 Cu1 O7 78.57(8) . . ? N1 Cu1 O7 96.46(9) . . ? N2 Cu1 O7 112.66(8) . . ? N4 O10 Cu1 108.21(16) . . ? C1 N1 C5 119.4(2) . . ? C1 N1 Cu1 125.93(19) . . ? C5 N1 Cu1 114.69(18) . . ? C10 N2 C6 119.0(2) . . ? C10 N2 Cu1 126.27(18) . . ? C6 N2 Cu1 114.70(18) . . ? N3 O7 Cu1 123.23(16) . . ? O5 N3 O6 122.8(3) . . ? O5 N3 O7 119.0(2) . . ? O6 N3 O7 118.2(2) . . ? O9 N4 O8 123.8(3) . . ? O9 N4 O10 118.7(2) . . ? O8 N4 O10 117.5(2) . . ? O3 C12 O4 125.9(3) . . ? O3 C12 C8 121.2(2) . . ? O4 C12 C8 112.8(2) . . ? O1 C11 O2 125.8(3) . . ? O1 C11 C3 118.5(2) . . ? O2 C11 C3 115.7(2) . . ? C9 C8 C7 119.5(2) . . ? C9 C8 C12 122.2(2) . . ? C7 C8 C12 118.3(2) . . ? N2 C6 C7 122.0(2) . . ? N2 C6 C5 114.3(2) . . ? C7 C6 C5 123.7(2) . . ? N1 C1 C2 122.1(2) . . ? C5 C4 C3 118.3(2) . . ? N1 C5 C4 121.9(2) . . ? N1 C5 C6 114.5(2) . . ? C4 C5 C6 123.6(2) . . ? N2 C10 C9 122.6(2) . . ? C6 C7 C8 118.9(2) . . ? C8 C9 C10 118.0(3) . . ? C2 C3 C4 119.5(2) . . ? C2 C3 C11 121.5(2) . . ? C4 C3 C11 119.0(2) . . ? C1 C2 C3 118.9(3) . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 29.98 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 3.024 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.109