# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Chang Seop Hong' _publ_contact_author_address ; Department of Chemistry and Center for Electro- and Photo-Responsive Molecules Korea University Seoul 136-701 SOUTH KOREA ; _publ_contact_author_email CSHONG@KOREA.AC.KR _publ_section_title ; Chiral azide-bridged two-dimensional Cu(II) compounds showing a field-induced spin-flop transition ; loop_ _publ_author_name 'Chang Seop Hong' 'Sang Jun Oh' 'Jung Hee Yoon' 'Young Sin You' data_complex1 _database_code_depnum_ccdc_archive 'CCDC 264622' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H28 Cu2 N16' _chemical_formula_weight 523.58 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' 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.9892(2) _cell_length_b 6.85890(10) _cell_length_c 13.2344(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.2820(10) _cell_angle_gamma 90.00 _cell_volume 1086.52(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 1.993 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9494 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 28.30 _reflns_number_total 4257 _reflns_number_gt 4115 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0251P)^2^+0.1705P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.030(10) _refine_ls_number_reflns 4257 _refine_ls_number_parameters 303 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0169 _refine_ls_R_factor_gt 0.0163 _refine_ls_wR_factor_ref 0.0473 _refine_ls_wR_factor_gt 0.0470 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 0.470798(15) 0.23523(2) 0.155209(15) 0.01047(6) Uani 1 1 d . . . N1 N 0.37164(13) 0.4714(3) 0.14286(15) 0.0125(4) Uani 1 1 d . . . H11 H 0.3683(19) 0.535(5) 0.199(2) 0.026(7) Uiso 1 1 d . . . H12 H 0.3984(18) 0.541(4) 0.0997(18) 0.021(6) Uiso 1 1 d . . . N2 N 0.32638(13) 0.0849(3) 0.14558(14) 0.0123(4) Uani 1 1 d . . . H21 H 0.336(2) -0.025(4) 0.188(2) 0.034(8) Uiso 1 1 d . . . H22 H 0.3112(17) 0.034(4) 0.0870(18) 0.013(6) Uiso 1 1 d . . . C1 C 0.25679(12) 0.4085(3) 0.11071(14) 0.0126(3) Uani 1 1 d . . . H2 H 0.2551 0.3774 0.0384 0.015 Uiso 1 1 calc R . . C2 C 0.23491(12) 0.2213(3) 0.16819(14) 0.0125(3) Uani 1 1 d . . . H1 H 0.2403 0.2501 0.2408 0.015 Uiso 1 1 calc R . . C3 C 0.11836(14) 0.1392(3) 0.14059(16) 0.0168(4) Uani 1 1 d . . . H6A H 0.1048 0.0273 0.1829 0.020 Uiso 1 1 calc R . . H6B H 0.1143 0.0964 0.0706 0.020 Uiso 1 1 calc R . . C4 C 0.02874(13) 0.2945(3) 0.15532(17) 0.0212(4) Uani 1 1 d . . . H5A H -0.0439 0.2432 0.1328 0.025 Uiso 1 1 calc R . . H5B H 0.0269 0.3258 0.2267 0.025 Uiso 1 1 calc R . . C5 C 0.05220(14) 0.4790(3) 0.09611(17) 0.0212(4) Uani 1 1 d . . . H4A H -0.0043 0.5759 0.1084 0.025 Uiso 1 1 calc R . . H4B H 0.0480 0.4497 0.0243 0.025 Uiso 1 1 calc R . . C6 C 0.16758(16) 0.5617(4) 0.12667(17) 0.0179(4) Uani 1 1 d . . . H3A H 0.1816 0.6761 0.0863 0.021 Uiso 1 1 calc R . . H3B H 0.1703 0.6004 0.1973 0.021 Uiso 1 1 calc R . . N3 N 0.60803(12) 0.3922(3) 0.18830(13) 0.0137(4) Uani 1 1 d . . . N4 N 0.67734(12) 0.4065(3) 0.12679(12) 0.0147(4) Uani 1 1 d . . . N5 N 0.74615(13) 0.4227(5) 0.06985(14) 0.0294(5) Uani 1 1 d . . . N6 N 0.56403(13) -0.0105(3) 0.15586(14) 0.0138(4) Uani 1 1 d . . . N7 N 0.53955(12) -0.1302(3) 0.09211(14) 0.0110(4) Uani 1 1 d . . . N8 N 0.51707(13) -0.2476(4) 0.03157(12) 0.0162(4) Uani 1 1 d . . . Cu2 Cu 0.531272(15) -0.06370(2) 0.347711(16) 0.01050(6) Uani 1 1 d . . . N9 N 0.67429(13) 0.0912(3) 0.36785(15) 0.0118(4) Uani 1 1 d . . . H91 H 0.6822(14) 0.159(3) 0.3083(16) 0.004(5) Uiso 1 1 d . . . H92 H 0.6718(18) 0.172(4) 0.4110(18) 0.017(6) Uiso 1 1 d . . . N10 N 0.63376(13) -0.2964(3) 0.34686(15) 0.0121(4) Uani 1 1 d . . . H101 H 0.6154(15) -0.381(4) 0.2964(17) 0.008(5) Uiso 1 1 d . . . H102 H 0.6338(17) -0.342(4) 0.3971(18) 0.013(6) Uiso 1 1 d . . . C7 C 0.76794(12) -0.0440(3) 0.39344(14) 0.0130(3) Uani 1 1 d . . . H7 H 0.7650 -0.0793 0.4650 0.016 Uiso 1 1 calc R . . C8 C 0.74895(13) -0.2279(3) 0.33111(15) 0.0129(3) Uani 1 1 d . . . H8 H 0.7527 -0.1929 0.2596 0.015 Uiso 1 1 calc R . . C9 C 0.83971(15) -0.3793(4) 0.35661(17) 0.0180(4) Uani 1 1 d . . . H9C H 0.8290 -0.4912 0.3123 0.022 Uiso 1 1 calc R . . H9D H 0.8344 -0.4234 0.4258 0.022 Uiso 1 1 calc R . . C10 C 0.95613(14) -0.2907(3) 0.34383(17) 0.0239(4) Uani 1 1 d . . . H10C H 1.0129 -0.3852 0.3650 0.029 Uiso 1 1 calc R . . H10D H 0.9644 -0.2617 0.2729 0.029 Uiso 1 1 calc R . . C11 C 0.97377(14) -0.1057(3) 0.40536(18) 0.0253(4) Uani 1 1 d . . . H11A H 1.0461 -0.0503 0.3925 0.030 Uiso 1 1 calc R . . H11B H 0.9735 -0.1367 0.4769 0.030 Uiso 1 1 calc R . . C12 C 0.88207(15) 0.0445(4) 0.37836(18) 0.0196(5) Uani 1 1 d . . . H12A H 0.8928 0.1587 0.4210 0.023 Uiso 1 1 calc R . . H12B H 0.8864 0.0848 0.3084 0.023 Uiso 1 1 calc R . . N11 N 0.43927(13) 0.1840(3) 0.34529(13) 0.0124(4) Uani 1 1 d . . . N12 N 0.46348(12) 0.3029(3) 0.40819(14) 0.0112(4) Uani 1 1 d . . . N13 N 0.48609(13) 0.4218(4) 0.46878(12) 0.0169(4) Uani 1 1 d . . . N14 N 0.39449(12) -0.2231(3) 0.31199(13) 0.0135(4) Uani 1 1 d . . . N15 N 0.32289(13) -0.2159(3) 0.37215(13) 0.0162(4) Uani 1 1 d . . . N16 N 0.25299(14) -0.2127(4) 0.42858(15) 0.0293(5) Uani 1 1 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 0.00981(10) 0.00915(14) 0.01237(14) -0.00089(11) -0.00008(8) -0.00060(9) N1 0.0137(7) 0.0107(10) 0.0131(9) -0.0018(8) 0.0013(6) -0.0028(7) N2 0.0128(7) 0.0116(9) 0.0123(9) -0.0006(8) -0.0007(6) -0.0006(7) C1 0.0128(7) 0.0123(7) 0.0124(9) -0.0007(8) -0.0009(6) 0.0015(6) C2 0.0113(7) 0.0139(7) 0.0123(9) -0.0010(8) -0.0005(5) 0.0002(6) C3 0.0128(8) 0.0153(10) 0.0221(10) -0.0005(10) -0.0001(7) -0.0030(8) C4 0.0116(7) 0.0260(10) 0.0260(11) -0.0021(10) 0.0002(7) -0.0005(7) C5 0.0154(8) 0.0246(9) 0.0232(11) 0.0006(10) -0.0023(7) 0.0052(7) C6 0.0169(9) 0.0162(10) 0.0205(10) 0.0016(10) 0.0009(7) 0.0045(8) N3 0.0133(7) 0.0141(11) 0.0138(9) -0.0038(9) 0.0015(5) -0.0040(7) N4 0.0138(7) 0.0152(9) 0.0144(8) 0.0039(9) -0.0037(5) 0.0005(7) N5 0.0147(7) 0.0521(14) 0.0218(9) 0.0087(11) 0.0039(6) 0.0007(9) N6 0.0145(7) 0.0126(10) 0.0140(9) -0.0023(8) -0.0018(6) 0.0007(7) N7 0.0104(7) 0.0116(10) 0.0109(8) 0.0035(9) 0.0015(5) 0.0007(7) N8 0.0225(8) 0.0145(11) 0.0118(9) 0.0006(10) 0.0023(6) -0.0004(9) Cu2 0.00993(10) 0.00925(13) 0.01222(13) -0.00120(11) -0.00011(8) -0.00032(9) N9 0.0122(7) 0.0092(9) 0.0139(9) -0.0017(8) -0.0007(6) 0.0009(7) N10 0.0133(7) 0.0111(10) 0.0119(9) 0.0006(9) 0.0012(6) 0.0001(7) C7 0.0120(7) 0.0128(7) 0.0141(9) -0.0005(8) -0.0017(6) 0.0017(6) C8 0.0120(7) 0.0140(7) 0.0127(9) -0.0007(8) 0.0014(6) 0.0003(6) C9 0.0175(9) 0.0133(10) 0.0231(11) -0.0035(10) -0.0007(7) 0.0036(8) C10 0.0131(7) 0.0253(9) 0.0332(12) -0.0060(11) 0.0007(7) 0.0055(7) C11 0.0134(7) 0.0256(10) 0.0364(13) -0.0046(11) -0.0041(7) 0.0019(7) C12 0.0113(8) 0.0194(11) 0.0276(12) -0.0046(10) -0.0018(7) -0.0004(8) N11 0.0150(7) 0.0110(10) 0.0109(9) 0.0005(8) -0.0024(6) 0.0014(7) N12 0.0120(7) 0.0110(10) 0.0109(8) 0.0045(8) 0.0020(5) 0.0021(7) N13 0.0255(8) 0.0136(10) 0.0116(9) -0.0019(11) 0.0013(6) -0.0032(9) N14 0.0122(7) 0.0142(11) 0.0141(9) 0.0002(8) 0.0011(5) -0.0018(7) N15 0.0124(7) 0.0210(10) 0.0148(9) 0.0042(9) -0.0029(5) 0.0004(7) N16 0.0155(7) 0.0481(14) 0.0247(10) 0.0113(10) 0.0056(6) 0.0050(8) _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 N3 1.9939(16) . ? Cu1 N1 2.011(2) . ? Cu1 N2 2.0130(17) . ? Cu1 N6 2.0222(19) . ? N1 C1 1.482(2) . ? N2 C2 1.485(2) . ? C1 C2 1.523(2) . ? C1 C6 1.523(3) . ? C2 C3 1.531(2) . ? C3 C4 1.533(3) . ? C4 C5 1.523(3) . ? C5 C6 1.528(3) . ? N3 N4 1.200(2) . ? N4 N5 1.154(2) . ? N6 N7 1.202(2) . ? N7 N8 1.157(3) . ? Cu2 N14 2.0047(17) . ? Cu2 N10 2.015(2) . ? Cu2 N9 2.0218(17) . ? Cu2 N11 2.0250(19) . ? Cu2 N13 2.4515(16) 2_646 ? N9 C7 1.480(2) . ? N10 C8 1.485(2) . ? C7 C8 1.517(2) . ? C7 C12 1.520(2) . ? C8 C9 1.528(3) . ? C9 C10 1.541(3) . ? C10 C11 1.516(3) . ? C11 C12 1.534(3) . ? N11 N12 1.189(3) . ? N12 N13 1.165(3) . ? N13 Cu2 2.4515(16) 2_656 ? N14 N15 1.205(2) . ? N15 N16 1.154(2) . ? 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 N3 Cu1 N1 93.41(7) . . ? N3 Cu1 N2 170.56(7) . . ? N1 Cu1 N2 84.55(8) . . ? N3 Cu1 N6 90.01(8) . . ? N1 Cu1 N6 174.92(7) . . ? N2 Cu1 N6 92.67(8) . . ? C1 N1 Cu1 108.90(14) . . ? C2 N2 Cu1 107.89(13) . . ? N1 C1 C2 106.62(14) . . ? N1 C1 C6 114.05(16) . . ? C2 C1 C6 111.72(15) . . ? N2 C2 C1 106.27(14) . . ? N2 C2 C3 113.26(16) . . ? C1 C2 C3 111.82(14) . . ? C2 C3 C4 110.55(17) . . ? C5 C4 C3 111.12(16) . . ? C4 C5 C6 111.30(16) . . ? C1 C6 C5 109.85(18) . . ? N4 N3 Cu1 119.32(14) . . ? N5 N4 N3 177.9(2) . . ? N7 N6 Cu1 116.99(13) . . ? N8 N7 N6 178.9(2) . . ? N14 Cu2 N10 93.31(8) . . ? N14 Cu2 N9 173.60(7) . . ? N10 Cu2 N9 84.49(8) . . ? N14 Cu2 N11 90.93(8) . . ? N10 Cu2 N11 175.18(8) . . ? N9 Cu2 N11 91.05(7) . . ? N14 Cu2 N13 95.56(7) . 2_646 ? N10 Cu2 N13 93.43(8) . 2_646 ? N9 Cu2 N13 90.58(7) . 2_646 ? N11 Cu2 N13 88.43(8) . 2_646 ? C7 N9 Cu2 109.11(13) . . ? C8 N10 Cu2 108.82(14) . . ? N9 C7 C8 107.95(13) . . ? N9 C7 C12 113.35(16) . . ? C8 C7 C12 111.63(15) . . ? N10 C8 C7 107.37(15) . . ? N10 C8 C9 114.22(16) . . ? C7 C8 C9 111.24(14) . . ? C8 C9 C10 110.22(18) . . ? C11 C10 C9 111.77(16) . . ? C10 C11 C12 111.15(16) . . ? C7 C12 C11 109.87(18) . . ? N12 N11 Cu2 116.95(12) . . ? N13 N12 N11 178.8(2) . . ? N12 N13 Cu2 132.91(18) . 2_656 ? N15 N14 Cu2 115.21(15) . . ? N16 N15 N14 178.3(3) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.235 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.066 data_complex2 _database_code_depnum_ccdc_archive 'CCDC 264623' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H28 Cu2 N16' _chemical_formula_weight 523.58 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' 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 P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.0004(4) _cell_length_b 6.8589(2) _cell_length_c 13.2287(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.2810(10) _cell_angle_gamma 90.00 _cell_volume 1087.06(6) _cell_formula_units_Z 2 _cell_measurement_temperature 100 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.600 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 540 _exptl_absorpt_coefficient_mu 1.992 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7763 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_sigmaI/netI 0.0286 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.54 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3709 _reflns_number_gt 3381 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0426P)^2^+1.0089P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.014(11) _refine_ls_number_reflns 3709 _refine_ls_number_parameters 303 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0208 _refine_ls_R_factor_gt 0.0180 _refine_ls_wR_factor_ref 0.0500 _refine_ls_wR_factor_gt 0.0483 _refine_ls_goodness_of_fit_ref 0.674 _refine_ls_restrained_S_all 0.674 _refine_ls_shift/su_max 0.005 _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 0.47076(2) -0.23521(3) 0.155174(18) 0.00947(8) Uani 1 1 d . . . N1 N 0.37109(18) -0.4708(4) 0.14269(17) 0.0112(5) Uani 1 1 d . . . H11 H 0.368(3) -0.533(6) 0.199(2) 0.032(10) Uiso 1 1 d . . . H12 H 0.398(2) -0.528(5) 0.099(2) 0.019(8) Uiso 1 1 d . . . N2 N 0.32669(18) -0.0848(4) 0.14549(15) 0.0112(5) Uani 1 1 d . . . H21 H 0.334(2) 0.028(5) 0.191(2) 0.023(8) Uiso 1 1 d . . . H22 H 0.308(2) -0.036(5) 0.085(2) 0.023(8) Uiso 1 1 d . . . C1 C 0.25667(17) -0.4086(3) 0.11083(15) 0.0118(4) Uani 1 1 d . . . H1 H 0.2551 -0.3775 0.0384 0.014 Uiso 1 1 calc R . . C2 C 0.23499(16) -0.2211(3) 0.16791(15) 0.0111(4) Uani 1 1 d . . . H2 H 0.2404 -0.2497 0.2406 0.013 Uiso 1 1 calc R . . C3 C 0.1186(2) -0.1390(5) 0.14051(18) 0.0156(6) Uani 1 1 d . . . H3A H 0.1145 -0.0959 0.0706 0.019 Uiso 1 1 calc R . . H3B H 0.1051 -0.0272 0.1830 0.019 Uiso 1 1 calc R . . C4 C 0.02879(18) -0.2945(4) 0.15515(18) 0.0196(5) Uani 1 1 d . . . H4A H 0.0268 -0.3257 0.2265 0.024 Uiso 1 1 calc R . . H4B H -0.0437 -0.2431 0.1325 0.024 Uiso 1 1 calc R . . C5 C 0.05229(19) -0.4787(4) 0.09611(18) 0.0201(5) Uani 1 1 d . . . H5A H 0.0478 -0.4496 0.0242 0.024 Uiso 1 1 calc R . . H5B H -0.0040 -0.5758 0.1086 0.024 Uiso 1 1 calc R . . C6 C 0.1676(2) -0.5611(5) 0.12632(19) 0.0164(6) Uani 1 1 d . . . H6A H 0.1704 -0.6005 0.1968 0.020 Uiso 1 1 calc R . . H6B H 0.1815 -0.6752 0.0856 0.020 Uiso 1 1 calc R . . N3 N 0.60751(17) -0.3931(4) 0.18838(15) 0.0133(6) Uani 1 1 d . . . N4 N 0.67716(16) -0.4054(4) 0.12696(14) 0.0133(5) Uani 1 1 d . . . N5 N 0.74581(18) -0.4220(6) 0.06984(15) 0.0269(6) Uani 1 1 d . . . N6 N 0.56343(18) 0.0105(4) 0.15587(15) 0.0128(6) Uani 1 1 d . . . N7 N 0.53941(16) 0.1302(4) 0.09205(16) 0.0100(5) Uani 1 1 d . . . N8 N 0.51693(17) 0.2477(5) 0.03149(13) 0.0153(5) Uani 1 1 d . . . Cu2 Cu 0.53127(2) 0.06367(3) 0.347747(18) 0.00948(8) Uani 1 1 d . . . N9 N 0.67429(18) -0.0911(4) 0.36801(16) 0.0106(5) Uani 1 1 d . . . H91 H 0.6819(18) -0.153(4) 0.3083(17) 0.002(6) Uiso 1 1 d . . . H92 H 0.672(2) -0.166(5) 0.410(2) 0.013(8) Uiso 1 1 d . . . N10 N 0.63382(18) 0.2966(4) 0.34713(17) 0.0119(5) Uani 1 1 d . . . H101 H 0.617(2) 0.379(4) 0.3010(19) 0.007(7) Uiso 1 1 d . . . H102 H 0.630(2) 0.359(5) 0.400(2) 0.016(7) Uiso 1 1 d . . . C7 C 0.76809(17) 0.0439(3) 0.39361(15) 0.0119(4) Uani 1 1 d . . . H7 H 0.7653 0.0791 0.4652 0.014 Uiso 1 1 calc R . . C8 C 0.74908(17) 0.2281(3) 0.33120(16) 0.0117(4) Uani 1 1 d . . . H8 H 0.7527 0.1930 0.2596 0.014 Uiso 1 1 calc R . . C9 C 0.8395(2) 0.3794(5) 0.35637(19) 0.0173(6) Uani 1 1 d . . . H9A H 0.8341 0.4239 0.4255 0.021 Uiso 1 1 calc R . . H9B H 0.8287 0.4909 0.3118 0.021 Uiso 1 1 calc R . . C10 C 0.95566(19) 0.2911(4) 0.34382(18) 0.0224(5) Uani 1 1 d . . . H10A H 0.9641 0.2624 0.2729 0.027 Uiso 1 1 calc R . . H10B H 1.0123 0.3857 0.3652 0.027 Uiso 1 1 calc R . . C11 C 0.97344(19) 0.1054(4) 0.4055(2) 0.0240(5) Uani 1 1 d . . . H11A H 0.9733 0.1363 0.4770 0.029 Uiso 1 1 calc R . . H11B H 1.0456 0.0500 0.3926 0.029 Uiso 1 1 calc R . . C12 C 0.8817(2) -0.0443(5) 0.3784(2) 0.0177(6) Uani 1 1 d . . . H12A H 0.8859 -0.0843 0.3084 0.021 Uiso 1 1 calc R . . H12B H 0.8924 -0.1588 0.4209 0.021 Uiso 1 1 calc R . . N11 N 0.43884(17) -0.1837(4) 0.34537(14) 0.0111(5) Uani 1 1 d . . . N12 N 0.46352(17) -0.3034(4) 0.40813(16) 0.0103(5) Uani 1 1 d . . . N13 N 0.48608(18) -0.4224(5) 0.46858(13) 0.0157(5) Uani 1 1 d . . . N14 N 0.39430(17) 0.2223(4) 0.31193(15) 0.0123(5) Uani 1 1 d . . . N15 N 0.32294(17) 0.2164(4) 0.37208(15) 0.0160(6) Uani 1 1 d . . . N16 N 0.25292(19) 0.2120(5) 0.42815(17) 0.0287(7) Uani 1 1 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 0.00846(15) 0.00840(19) 0.01142(14) 0.00081(12) -0.00057(10) 0.00035(14) N1 0.0120(11) 0.0095(14) 0.0125(9) 0.0015(9) 0.0021(7) 0.0030(10) N2 0.0118(11) 0.0112(14) 0.0104(9) 0.0001(8) -0.0016(7) -0.0014(10) C1 0.0113(10) 0.0127(11) 0.0113(9) -0.0003(8) -0.0016(7) -0.0019(9) C2 0.0085(9) 0.0138(11) 0.0108(9) 0.0012(8) -0.0007(7) -0.0006(8) C3 0.0120(12) 0.0160(15) 0.0189(10) 0.0014(10) 0.0008(8) 0.0031(11) C4 0.0100(11) 0.0245(14) 0.0242(11) 0.0024(10) -0.0007(8) 0.0003(10) C5 0.0128(11) 0.0251(14) 0.0218(11) 0.0010(10) -0.0030(8) -0.0075(10) C6 0.0151(13) 0.0150(15) 0.0191(11) -0.0024(10) 0.0000(8) -0.0050(11) N3 0.0109(10) 0.0155(17) 0.0135(10) 0.0042(10) 0.0019(7) 0.0042(11) N4 0.0124(10) 0.0132(14) 0.0138(9) -0.0033(9) -0.0047(7) -0.0004(11) N5 0.0131(10) 0.0478(18) 0.0200(10) -0.0101(12) 0.0034(7) -0.0010(13) N6 0.0126(11) 0.0120(16) 0.0136(10) 0.0022(9) -0.0022(7) 0.0008(10) N7 0.0089(10) 0.0114(14) 0.0098(8) -0.0036(9) 0.0021(7) 0.0003(10) N8 0.0210(11) 0.0139(15) 0.0112(9) -0.0005(12) 0.0020(7) -0.0004(13) Cu2 0.00832(15) 0.00843(19) 0.01157(14) 0.00106(12) -0.00045(10) 0.00055(15) N9 0.0102(11) 0.0094(13) 0.0120(9) 0.0029(9) -0.0019(7) 0.0008(10) N10 0.0120(10) 0.0114(14) 0.0122(9) -0.0004(9) 0.0000(7) -0.0001(10) C7 0.0104(10) 0.0118(11) 0.0132(9) 0.0003(9) -0.0018(7) -0.0021(8) C8 0.0099(10) 0.0138(11) 0.0115(9) 0.0006(8) 0.0006(7) -0.0004(8) C9 0.0145(13) 0.0140(15) 0.0234(11) 0.0043(10) 0.0002(9) -0.0037(11) C10 0.0106(11) 0.0248(14) 0.0317(12) 0.0068(11) 0.0002(9) -0.0042(10) C11 0.0126(11) 0.0238(14) 0.0349(13) 0.0065(12) -0.0042(9) -0.0022(10) C12 0.0100(12) 0.0162(15) 0.0267(12) 0.0045(11) -0.0005(9) 0.0008(11) N11 0.0124(10) 0.0108(15) 0.0099(9) -0.0004(9) -0.0025(7) -0.0027(10) N12 0.0101(10) 0.0103(14) 0.0106(9) -0.0040(9) 0.0014(7) -0.0031(10) N13 0.0245(11) 0.0116(14) 0.0110(10) 0.0012(11) 0.0007(7) 0.0025(14) N14 0.0117(11) 0.0127(16) 0.0124(9) -0.0003(9) 0.0005(7) 0.0011(11) N15 0.0118(10) 0.0207(16) 0.0151(10) -0.0046(10) -0.0029(7) -0.0012(11) N16 0.0130(11) 0.050(2) 0.0234(11) -0.0118(12) 0.0058(8) -0.0055(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N3 1.994(2) . ? Cu1 N2 2.011(2) . ? Cu1 N1 2.011(3) . ? Cu1 N6 2.019(3) . ? N1 C1 1.476(3) . ? N2 C2 1.487(3) . ? C1 C6 1.518(4) . ? C1 C2 1.521(3) . ? C2 C3 1.530(3) . ? C3 C4 1.536(4) . ? C4 C5 1.520(4) . ? C5 C6 1.526(3) . ? N3 N4 1.201(3) . ? N4 N5 1.155(3) . ? N6 N7 1.201(3) . ? N7 N8 1.157(3) . ? Cu2 N14 2.005(2) . ? Cu2 N10 2.017(3) . ? Cu2 N9 2.023(2) . ? Cu2 N11 2.026(2) . ? Cu2 N13 2.4524(18) 2_656 ? N9 C7 1.481(3) . ? N10 C8 1.487(3) . ? C7 C12 1.515(3) . ? C7 C8 1.519(3) . ? C8 C9 1.525(4) . ? C9 C10 1.537(3) . ? C10 C11 1.521(3) . ? C11 C12 1.533(4) . ? N11 N12 1.193(3) . ? N12 N13 1.164(3) . ? N13 Cu2 2.4524(18) 2_646 ? N14 N15 1.203(3) . ? N15 N16 1.153(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 N3 Cu1 N2 170.50(9) . . ? N3 Cu1 N1 93.43(10) . . ? N2 Cu1 N1 84.36(11) . . ? N3 Cu1 N6 90.36(10) . . ? N2 Cu1 N6 92.49(10) . . ? N1 Cu1 N6 174.70(9) . . ? C1 N1 Cu1 109.29(18) . . ? C2 N2 Cu1 107.97(17) . . ? N1 C1 C6 114.4(2) . . ? N1 C1 C2 106.58(18) . . ? C6 C1 C2 111.94(19) . . ? N2 C2 C1 106.43(17) . . ? N2 C2 C3 113.4(2) . . ? C1 C2 C3 111.90(18) . . ? C2 C3 C4 110.6(2) . . ? C5 C4 C3 111.1(2) . . ? C4 C5 C6 111.4(2) . . ? C1 C6 C5 110.2(2) . . ? N4 N3 Cu1 118.99(18) . . ? N5 N4 N3 177.7(3) . . ? N7 N6 Cu1 117.22(17) . . ? N8 N7 N6 179.0(3) . . ? N14 Cu2 N10 93.52(10) . . ? N14 Cu2 N9 173.65(8) . . ? N10 Cu2 N9 84.42(11) . . ? N14 Cu2 N11 90.58(10) . . ? N10 Cu2 N11 175.37(11) . . ? N9 Cu2 N11 91.28(10) . . ? N14 Cu2 N13 95.63(8) . 2_656 ? N10 Cu2 N13 93.41(10) . 2_656 ? N9 Cu2 N13 90.49(8) . 2_656 ? N11 Cu2 N13 88.31(9) . 2_656 ? C7 N9 Cu2 109.29(17) . . ? C8 N10 Cu2 108.84(19) . . ? N9 C7 C12 113.4(2) . . ? N9 C7 C8 107.87(17) . . ? C12 C7 C8 111.59(19) . . ? N10 C8 C7 107.32(18) . . ? N10 C8 C9 114.2(2) . . ? C7 C8 C9 111.38(18) . . ? C8 C9 C10 110.3(2) . . ? C11 C10 C9 111.8(2) . . ? C10 C11 C12 111.0(2) . . ? C7 C12 C11 109.9(2) . . ? N12 N11 Cu2 116.84(16) . . ? N13 N12 N11 178.7(3) . . ? N12 N13 Cu2 132.7(2) . 2_646 ? N15 N14 Cu2 115.49(19) . . ? N16 N15 N14 178.5(3) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.259 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.058