Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Gaelle Ramon' _publ_contact_author_address ; Chemistry University of Cape Town Supramolecular Chemistry Group PD Hahn Building Rondebosch Cape Town 7701 SOUTH AFRICA ; _publ_contact_author_email GAELLE.RAMON@UCT.AC.ZA _publ_section_title ; Coordination chemistry of N,N,4-tris (pyridin-2-ylmethyl) aniline: a novel flexible, multimodal ligand. ; loop_ _publ_author_name 'Gaelle Ramon' 'Ann Almesaker' 'Susan Bourne' 'Janet Scott' 'Christopher R. Strauss' data_gr8 _database_code_depnum_ccdc_archive 'CCDC 649296' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N,N,4-tris(pyridin-2-ylmethyl)aniline ; _chemical_name_common N,N,4-tris(pyridin-2-ylmethyl)aniline _chemical_melting_point 88.3-88.8 _chemical_formula_moiety 'C24 H22 N4' _chemical_formula_sum 'C24 H22 N4' _chemical_formula_weight 366.46 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.4861(19) _cell_length_b 6.0392(12) _cell_length_c 32.990(7) _cell_angle_alpha 90.00 _cell_angle_beta 95.82(3) _cell_angle_gamma 90.00 _cell_volume 1880.2(7) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 28.0 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 46476 _diffrn_reflns_av_R_equivalents 0.0540 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -43 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.97 _reflns_number_total 4484 _reflns_number_gt 3846 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0402P)^2^+0.8691P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0099(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4484 _refine_ls_number_parameters 254 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0653 _refine_ls_R_factor_gt 0.0535 _refine_ls_wR_factor_ref 0.1187 _refine_ls_wR_factor_gt 0.1125 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.104 _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 N1 N 0.55751(13) 0.3344(2) 0.18106(4) 0.0215(3) Uani 1 1 d . . . C6 C 0.38810(15) 0.0774(2) 0.14684(4) 0.0214(3) Uani 1 1 d . . . H6 H 0.4113 -0.0290 0.1677 0.026 Uiso 1 1 calc R . . N3 N 0.81266(13) 0.7522(2) 0.15171(4) 0.0249(3) Uani 1 1 d . . . N4 N 0.27803(15) -0.1543(2) 0.01019(4) 0.0321(3) Uani 1 1 d . . . N2 N 0.54894(14) -0.1021(2) 0.25785(4) 0.0266(3) Uani 1 1 d . . . C13 C 0.63367(16) 0.5425(2) 0.18146(4) 0.0226(3) Uani 1 1 d . . . H13B H 0.6777 0.5701 0.2095 0.027 Uiso 1 1 calc R . . H13A H 0.5646 0.6629 0.1745 0.027 Uiso 1 1 calc R . . C1 C 0.45577(14) 0.2839(2) 0.14907(4) 0.0199(3) Uani 1 1 d . . . C2 C 0.41524(15) 0.4368(2) 0.11801(4) 0.0224(3) Uani 1 1 d . . . H2 H 0.4578 0.5794 0.1188 0.027 Uiso 1 1 calc R . . C4 C 0.24867(15) 0.1766(3) 0.08365(4) 0.0233(3) Uani 1 1 d . . . C14 C 0.74827(15) 0.5546(2) 0.15257(4) 0.0212(3) Uani 1 1 d . . . C8 C 0.52341(15) 0.0982(3) 0.24141(4) 0.0216(3) Uani 1 1 d . . . C3 C 0.31417(16) 0.3832(3) 0.08619(5) 0.0238(3) Uani 1 1 d . . . H3 H 0.2890 0.4901 0.0656 0.029 Uiso 1 1 calc R . . C19 C 0.14730(16) 0.1137(3) 0.04681(4) 0.0273(3) Uani 1 1 d . . . H19A H 0.0884 -0.0134 0.0538 0.033 Uiso 1 1 calc R . . H19B H 0.0834 0.2398 0.0391 0.033 Uiso 1 1 calc R . . C7 C 0.61597(15) 0.1612(2) 0.20843(4) 0.0215(3) Uani 1 1 d . . . H7B H 0.7091 0.2110 0.2215 0.026 Uiso 1 1 calc R . . H7A H 0.6323 0.0277 0.1921 0.026 Uiso 1 1 calc R . . C15 C 0.78337(16) 0.3762(3) 0.12924(5) 0.0246(3) Uani 1 1 d . . . H15 H 0.7351 0.2390 0.1307 0.030 Uiso 1 1 calc R . . C5 C 0.28762(15) 0.0261(3) 0.11461(4) 0.0225(3) Uani 1 1 d . . . H5 H 0.2443 -0.1159 0.1137 0.027 Uiso 1 1 calc R . . C16 C 0.88983(16) 0.4004(3) 0.10377(5) 0.0277(3) Uani 1 1 d . . . H16 H 0.9147 0.2812 0.0871 0.033 Uiso 1 1 calc R . . C21 C 0.25426(17) 0.2100(3) -0.01764(5) 0.0291(4) Uani 1 1 d . . . H21 H 0.2148 0.3542 -0.0165 0.035 Uiso 1 1 calc R . . C9 C 0.42264(16) 0.2407(3) 0.25416(5) 0.0294(4) Uani 1 1 d . . . H9 H 0.4069 0.3818 0.2418 0.035 Uiso 1 1 calc R . . C20 C 0.22815(15) 0.0528(3) 0.01122(4) 0.0247(3) Uani 1 1 d . . . C17 C 0.95888(16) 0.6010(3) 0.10309(5) 0.0284(4) Uani 1 1 d . . . H17 H 1.0333 0.6225 0.0863 0.034 Uiso 1 1 calc R . . C22 C 0.33792(18) 0.1564(3) -0.04807(5) 0.0345(4) Uani 1 1 d . . . H22 H 0.3571 0.2629 -0.0680 0.041 Uiso 1 1 calc R . . C18 C 0.91721(16) 0.7702(3) 0.12751(5) 0.0286(4) Uani 1 1 d . . . H18 H 0.9657 0.9076 0.1271 0.034 Uiso 1 1 calc R . . C24 C 0.35961(18) -0.2022(3) -0.01980(6) 0.0367(4) Uani 1 1 d . . . H24 H 0.3966 -0.3481 -0.0208 0.044 Uiso 1 1 calc R . . C12 C 0.47289(18) -0.1625(3) 0.28817(5) 0.0333(4) Uani 1 1 d . . . H12 H 0.4905 -0.3039 0.3002 0.040 Uiso 1 1 calc R . . C10 C 0.34503(18) 0.1731(4) 0.28539(5) 0.0389(4) Uani 1 1 d . . . H10 H 0.2747 0.2672 0.2946 0.047 Uiso 1 1 calc R . . C23 C 0.39295(17) -0.0536(3) -0.04906(5) 0.0356(4) Uani 1 1 d . . . H23 H 0.4523 -0.0952 -0.0693 0.043 Uiso 1 1 calc R . . C11 C 0.37089(18) -0.0315(3) 0.30281(5) 0.0376(4) Uani 1 1 d . . . H11 H 0.3197 -0.0810 0.3244 0.045 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 N1 0.0231(6) 0.0194(6) 0.0219(6) 0.0001(5) 0.0027(5) -0.0019(5) C6 0.0208(7) 0.0227(7) 0.0212(7) 0.0018(6) 0.0048(5) 0.0018(6) N3 0.0229(6) 0.0223(7) 0.0296(7) 0.0014(5) 0.0032(5) -0.0012(5) N4 0.0305(7) 0.0284(8) 0.0370(8) -0.0013(6) 0.0008(6) -0.0013(6) N2 0.0302(7) 0.0274(7) 0.0220(6) 0.0007(5) 0.0019(5) -0.0049(5) C13 0.0245(7) 0.0201(7) 0.0238(7) -0.0018(6) 0.0052(6) -0.0016(6) C1 0.0184(7) 0.0220(7) 0.0199(7) -0.0018(6) 0.0054(5) 0.0017(5) C2 0.0235(7) 0.0202(7) 0.0244(7) 0.0011(6) 0.0073(6) 0.0003(6) C4 0.0186(7) 0.0308(8) 0.0211(7) -0.0006(6) 0.0052(5) 0.0014(6) C14 0.0201(7) 0.0214(7) 0.0216(7) 0.0015(6) 0.0002(5) 0.0007(6) C8 0.0183(7) 0.0269(8) 0.0192(7) -0.0012(6) 0.0000(5) -0.0024(6) C3 0.0234(7) 0.0261(8) 0.0230(7) 0.0045(6) 0.0070(6) 0.0038(6) C19 0.0208(7) 0.0376(9) 0.0237(8) 0.0012(7) 0.0037(6) -0.0009(6) C7 0.0202(7) 0.0227(7) 0.0217(7) 0.0003(6) 0.0031(5) 0.0007(6) C15 0.0243(7) 0.0232(8) 0.0267(8) -0.0008(6) 0.0044(6) -0.0013(6) C5 0.0198(7) 0.0238(8) 0.0249(7) -0.0015(6) 0.0064(6) -0.0018(6) C16 0.0253(8) 0.0310(9) 0.0271(8) -0.0018(6) 0.0046(6) 0.0031(6) C21 0.0282(8) 0.0330(9) 0.0260(8) 0.0029(7) 0.0024(6) 0.0043(7) C9 0.0252(8) 0.0382(9) 0.0249(8) -0.0007(7) 0.0025(6) 0.0064(7) C20 0.0190(7) 0.0310(8) 0.0232(7) -0.0011(6) -0.0021(6) -0.0010(6) C17 0.0222(7) 0.0360(9) 0.0280(8) 0.0059(7) 0.0066(6) 0.0013(6) C22 0.0316(9) 0.0489(11) 0.0235(8) 0.0035(7) 0.0047(7) -0.0007(8) C18 0.0234(7) 0.0281(8) 0.0346(9) 0.0057(7) 0.0038(6) -0.0026(6) C24 0.0298(9) 0.0324(9) 0.0470(10) -0.0145(8) -0.0009(8) 0.0022(7) C12 0.0385(9) 0.0373(9) 0.0240(8) 0.0019(7) 0.0021(7) -0.0142(8) C10 0.0247(8) 0.0643(13) 0.0287(9) -0.0072(9) 0.0078(7) 0.0047(8) C23 0.0253(8) 0.0538(12) 0.0279(8) -0.0146(8) 0.0029(7) -0.0009(8) C11 0.0274(8) 0.0622(13) 0.0238(8) 0.0004(8) 0.0058(7) -0.0169(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 N1 C1 1.3900(18) . ? N1 C13 1.4491(19) . ? N1 C7 1.4545(18) . ? C6 C5 1.389(2) . ? C6 C1 1.401(2) . ? N3 C18 1.339(2) . ? N3 C14 1.3420(19) . ? N4 C20 1.339(2) . ? N4 C24 1.348(2) . ? N2 C8 1.338(2) . ? N2 C12 1.342(2) . ? C13 C14 1.518(2) . ? C1 C2 1.404(2) . ? C2 C3 1.386(2) . ? C4 C5 1.389(2) . ? C4 C3 1.393(2) . ? C4 C19 1.520(2) . ? C14 C15 1.384(2) . ? C8 C9 1.383(2) . ? C8 C7 1.514(2) . ? C19 C20 1.511(2) . ? C15 C16 1.385(2) . ? C16 C17 1.379(2) . ? C21 C22 1.380(2) . ? C21 C20 1.385(2) . ? C9 C10 1.387(2) . ? C17 C18 1.383(2) . ? C22 C23 1.373(3) . ? C24 C23 1.378(3) . ? C12 C11 1.375(3) . ? C10 C11 1.374(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 C1 N1 C13 120.29(12) . . ? C1 N1 C7 120.35(12) . . ? C13 N1 C7 117.38(12) . . ? C5 C6 C1 120.92(14) . . ? C18 N3 C14 116.81(13) . . ? C20 N4 C24 116.73(15) . . ? C8 N2 C12 117.32(15) . . ? N1 C13 C14 115.09(12) . . ? N1 C1 C6 120.95(13) . . ? N1 C1 C2 121.84(13) . . ? C6 C1 C2 117.20(13) . . ? C3 C2 C1 121.07(14) . . ? C5 C4 C3 117.26(13) . . ? C5 C4 C19 121.62(14) . . ? C3 C4 C19 120.95(14) . . ? N3 C14 C15 123.00(14) . . ? N3 C14 C13 114.34(13) . . ? C15 C14 C13 122.66(13) . . ? N2 C8 C9 122.79(14) . . ? N2 C8 C7 115.10(13) . . ? C9 C8 C7 122.09(14) . . ? C2 C3 C4 121.67(14) . . ? C20 C19 C4 110.63(12) . . ? N1 C7 C8 114.48(12) . . ? C16 C15 C14 119.11(14) . . ? C4 C5 C6 121.85(14) . . ? C17 C16 C15 118.64(15) . . ? C22 C21 C20 119.70(16) . . ? C8 C9 C10 118.57(17) . . ? N4 C20 C21 122.33(15) . . ? N4 C20 C19 117.11(14) . . ? C21 C20 C19 120.48(14) . . ? C16 C17 C18 118.39(14) . . ? C23 C22 C21 118.82(17) . . ? N3 C18 C17 124.03(15) . . ? N4 C24 C23 124.32(17) . . ? N2 C12 C11 123.81(17) . . ? C11 C10 C9 119.31(17) . . ? C22 C23 C24 118.05(16) . . ? C10 C11 C12 118.19(16) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.97 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.216 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.041 # Attachment 'structure__2_.cif' data_c:\gaelle~1\articl~2\struct~2\(2)-mn~1\ann1 _database_code_depnum_ccdc_archive 'CCDC 649297' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety '[Mn(tpma)Cl2]' _chemical_formula_sum 'C24 H22 Cl2 Mn N4' _chemical_formula_weight 492.30 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.7284(2) _cell_length_b 17.3023(3) _cell_length_c 15.7446(4) _cell_angle_alpha 90.00 _cell_angle_beta 102.2360(10) _cell_angle_gamma 90.00 _cell_volume 2323.75(9) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 27.9 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1012 _exptl_absorpt_coefficient_mu 0.817 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 22207 _diffrn_reflns_av_R_equivalents 0.0998 _diffrn_reflns_av_sigmaI/netI 0.0829 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.87 _reflns_number_total 5541 _reflns_number_gt 3746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5541 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.1251 _refine_ls_wR_factor_gt 0.1032 _refine_ls_goodness_of_fit_ref 0.782 _refine_ls_restrained_S_all 0.782 _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 Mn1 Mn 0.07989(4) 0.06286(2) 0.79873(2) 0.01667(12) Uani 1 1 d . . . Cl1 Cl 0.02492(6) 0.09592(3) 0.93505(4) 0.02080(15) Uani 1 1 d . . . Cl2 Cl 0.10890(7) 0.16577(4) 0.70474(4) 0.02771(17) Uani 1 1 d . . . C2 C 0.1283(3) -0.06764(13) 0.65079(15) 0.0186(5) Uani 1 1 d . . . H2 H 0.1105 -0.0135 0.6504 0.022 Uiso 1 1 calc R . . C11 C 0.6069(3) 0.06082(15) 0.87504(16) 0.0251(5) Uani 1 1 d . . . H11 H 0.6894 0.0962 0.8732 0.030 Uiso 1 1 calc R . . N2 N 0.3327(2) 0.03178(11) 0.83943(12) 0.0185(4) Uani 1 1 d . . . C10 C 0.6384(3) -0.01031(15) 0.91504(15) 0.0233(5) Uani 1 1 d . . . H10 H 0.7426 -0.0243 0.9420 0.028 Uiso 1 1 calc R . . C4 C 0.1794(3) -0.18362(14) 0.57497(15) 0.0201(5) Uani 1 1 d . . . N3 N -0.1554(2) 0.01612(12) 0.73331(13) 0.0220(4) Uani 1 1 d . . . C9 C 0.5154(3) -0.06060(14) 0.91509(15) 0.0213(5) Uani 1 1 d . . . H9 H 0.5344 -0.1104 0.9406 0.026 Uiso 1 1 calc R . . C8 C 0.3644(3) -0.03773(13) 0.87763(14) 0.0174(5) Uani 1 1 d . . . C12 C 0.4533(3) 0.07963(14) 0.83774(16) 0.0219(5) Uani 1 1 d . . . H12 H 0.4323 0.1283 0.8098 0.026 Uiso 1 1 calc R . . C7 C 0.2233(3) -0.08750(14) 0.88083(15) 0.0191(5) Uani 1 1 d . . . H7A H 0.2534 -0.1427 0.8823 0.023 Uiso 1 1 calc R . . H7B H 0.1850 -0.0759 0.9343 0.023 Uiso 1 1 calc R . . N1 N 0.0972(2) -0.07246(11) 0.80356(11) 0.0168(4) Uani 1 1 d . . . C13 C -0.0580(3) -0.09719(14) 0.81849(16) 0.0218(5) Uani 1 1 d . . . H13B H -0.0672 -0.0835 0.8782 0.026 Uiso 1 1 calc R . . H13A H -0.0693 -0.1539 0.8117 0.026 Uiso 1 1 calc R . . N4 N 0.4115(2) -0.22007(13) 0.40943(14) 0.0282(5) Uani 1 1 d . . . C18 C -0.2668(3) 0.05585(16) 0.67862(17) 0.0287(6) Uani 1 1 d . . . H18 H -0.2462 0.1077 0.6646 0.034 Uiso 1 1 calc R . . C1 C 0.1291(2) -0.11000(13) 0.72535(14) 0.0172(5) Uani 1 1 d . . . C14 C -0.1849(3) -0.05694(14) 0.75308(16) 0.0220(5) Uani 1 1 d . . . C3 C 0.1537(3) -0.10437(14) 0.57622(15) 0.0222(5) Uani 1 1 d . . . H3 H 0.1534 -0.0748 0.5254 0.027 Uiso 1 1 calc R . . C20 C 0.3828(3) -0.22680(13) 0.48976(15) 0.0212(5) Uani 1 1 d . . . C5 C 0.1781(3) -0.22538(15) 0.65039(16) 0.0273(6) Uani 1 1 d . . . H5 H 0.1943 -0.2797 0.6507 0.033 Uiso 1 1 calc R . . C19 C 0.2111(3) -0.22381(15) 0.49527(16) 0.0243(5) Uani 1 1 d . . . H19A H 0.1516 -0.1970 0.4430 0.029 Uiso 1 1 calc R . . H19B H 0.1708 -0.2774 0.4942 0.029 Uiso 1 1 calc R . . C21 C 0.5029(3) -0.23815(15) 0.56204(16) 0.0265(6) Uani 1 1 d . . . H21 H 0.4796 -0.2428 0.6181 0.032 Uiso 1 1 calc R . . C24 C 0.5618(3) -0.22354(16) 0.40116(19) 0.0332(6) Uani 1 1 d . . . H24 H 0.5829 -0.2182 0.3447 0.040 Uiso 1 1 calc R . . C23 C 0.6879(3) -0.23450(16) 0.4708(2) 0.0341(6) Uani 1 1 d . . . H23 H 0.7923 -0.2363 0.4622 0.041 Uiso 1 1 calc R . . C15 C -0.3261(3) -0.09339(17) 0.71834(19) 0.0327(6) Uani 1 1 d . . . H15 H -0.3439 -0.1454 0.7329 0.039 Uiso 1 1 calc R . . C6 C 0.1537(3) -0.18938(14) 0.72483(16) 0.0252(5) Uani 1 1 d . . . H6 H 0.1537 -0.2189 0.7757 0.030 Uiso 1 1 calc R . . C16 C -0.4408(3) -0.05177(19) 0.6618(2) 0.0427(8) Uani 1 1 d . . . H16 H -0.5386 -0.0751 0.6370 0.051 Uiso 1 1 calc R . . C17 C -0.4110(3) 0.02336(18) 0.6420(2) 0.0398(8) Uani 1 1 d . . . H17 H -0.4883 0.0527 0.6038 0.048 Uiso 1 1 calc R . . C22 C 0.6569(3) -0.24263(16) 0.55242(18) 0.0334(6) Uani 1 1 d . . . H22 H 0.7396 -0.2512 0.6014 0.040 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 Mn1 0.01495(19) 0.0180(2) 0.0169(2) -0.00012(14) 0.00308(14) 0.00039(13) Cl1 0.0198(3) 0.0255(3) 0.0174(3) -0.0009(2) 0.0047(2) 0.0018(2) Cl2 0.0256(3) 0.0294(3) 0.0290(3) 0.0113(3) 0.0076(2) 0.0032(3) C2 0.0200(11) 0.0189(12) 0.0174(11) -0.0004(9) 0.0049(9) 0.0015(9) C11 0.0189(12) 0.0313(14) 0.0263(13) -0.0074(11) 0.0075(10) -0.0049(10) N2 0.0178(10) 0.0190(10) 0.0188(10) -0.0007(8) 0.0040(8) 0.0014(8) C10 0.0160(11) 0.0367(15) 0.0166(12) -0.0083(10) 0.0018(9) 0.0050(10) C4 0.0173(11) 0.0259(13) 0.0171(11) -0.0069(10) 0.0039(9) -0.0040(10) N3 0.0161(9) 0.0272(11) 0.0223(10) -0.0047(9) 0.0033(8) 0.0008(8) C9 0.0250(12) 0.0241(13) 0.0149(11) -0.0037(9) 0.0044(10) 0.0056(10) C8 0.0194(11) 0.0218(12) 0.0115(11) -0.0033(9) 0.0044(9) 0.0014(9) C12 0.0219(12) 0.0202(12) 0.0250(13) -0.0016(10) 0.0084(10) -0.0017(10) C7 0.0229(12) 0.0198(12) 0.0148(11) 0.0012(9) 0.0043(9) 0.0006(10) N1 0.0163(9) 0.0206(10) 0.0144(10) -0.0023(7) 0.0054(8) -0.0015(7) C13 0.0218(12) 0.0236(13) 0.0226(13) -0.0039(10) 0.0102(10) -0.0034(10) N4 0.0312(12) 0.0321(12) 0.0236(11) 0.0006(9) 0.0106(9) 0.0045(10) C18 0.0247(13) 0.0322(14) 0.0278(14) -0.0044(11) 0.0028(11) 0.0053(11) C1 0.0156(10) 0.0219(12) 0.0150(11) -0.0053(9) 0.0053(9) -0.0045(9) C14 0.0184(11) 0.0289(14) 0.0207(12) -0.0088(10) 0.0084(9) -0.0022(10) C3 0.0223(11) 0.0284(14) 0.0160(12) 0.0008(10) 0.0042(9) 0.0015(10) C20 0.0262(12) 0.0165(12) 0.0212(12) -0.0045(9) 0.0061(10) -0.0019(10) C5 0.0373(14) 0.0183(13) 0.0282(13) -0.0045(10) 0.0108(11) -0.0026(11) C19 0.0243(12) 0.0286(14) 0.0208(12) -0.0090(10) 0.0066(10) -0.0016(10) C21 0.0278(13) 0.0293(14) 0.0220(12) -0.0040(11) 0.0041(10) -0.0003(11) C24 0.0369(15) 0.0346(15) 0.0335(15) 0.0058(12) 0.0200(12) 0.0075(12) C23 0.0258(13) 0.0288(15) 0.0505(18) -0.0004(13) 0.0142(13) 0.0015(11) C15 0.0234(13) 0.0330(15) 0.0405(16) -0.0129(13) 0.0041(12) -0.0059(11) C6 0.0356(14) 0.0204(13) 0.0214(13) -0.0010(10) 0.0104(11) -0.0035(11) C16 0.0208(13) 0.050(2) 0.0520(19) -0.0211(15) -0.0041(13) -0.0034(13) C17 0.0224(13) 0.0461(18) 0.0440(18) -0.0132(14) -0.0089(12) 0.0071(13) C22 0.0271(13) 0.0339(15) 0.0364(16) -0.0044(12) 0.0004(11) 0.0037(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 Mn1 N2 2.2294(18) . ? Mn1 N3 2.2441(19) . ? Mn1 N1 2.3464(19) . ? Mn1 Cl2 2.3629(7) . ? Mn1 Cl1 2.3667(7) . ? C2 C1 1.383(3) . ? C2 C3 1.394(3) . ? C11 C10 1.383(4) . ? C11 C12 1.384(3) . ? N2 C12 1.344(3) . ? N2 C8 1.347(3) . ? C10 C9 1.382(4) . ? C4 C3 1.390(3) . ? C4 C5 1.392(4) . ? C4 C19 1.511(3) . ? N3 C14 1.340(3) . ? N3 C18 1.343(3) . ? C9 C8 1.383(3) . ? C8 C7 1.512(3) . ? C7 N1 1.480(3) . ? N1 C1 1.470(3) . ? N1 C13 1.487(3) . ? C13 C14 1.513(3) . ? N4 C20 1.345(3) . ? N4 C24 1.347(3) . ? C18 C17 1.387(4) . ? C1 C6 1.390(3) . ? C14 C15 1.389(3) . ? C20 C21 1.388(3) . ? C20 C19 1.520(3) . ? C5 C6 1.383(4) . ? C21 C22 1.386(4) . ? C24 C23 1.392(4) . ? C23 C22 1.376(4) . ? C15 C16 1.391(4) . ? C16 C17 1.374(5) . ? 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 N2 Mn1 N3 143.02(7) . . ? N2 Mn1 N1 72.35(7) . . ? N3 Mn1 N1 72.65(7) . . ? N2 Mn1 Cl2 97.52(5) . . ? N3 Mn1 Cl2 101.14(6) . . ? N1 Mn1 Cl2 139.24(5) . . ? N2 Mn1 Cl1 100.15(5) . . ? N3 Mn1 Cl1 99.30(6) . . ? N1 Mn1 Cl1 103.65(5) . . ? Cl2 Mn1 Cl1 117.07(3) . . ? C1 C2 C3 120.0(2) . . ? C10 C11 C12 118.9(2) . . ? C12 N2 C8 118.1(2) . . ? C12 N2 Mn1 125.28(16) . . ? C8 N2 Mn1 116.15(15) . . ? C9 C10 C11 118.8(2) . . ? C3 C4 C5 118.0(2) . . ? C3 C4 C19 121.6(2) . . ? C5 C4 C19 120.4(2) . . ? C14 N3 C18 118.9(2) . . ? C14 N3 Mn1 115.83(15) . . ? C18 N3 Mn1 125.28(17) . . ? C10 C9 C8 119.3(2) . . ? N2 C8 C9 122.2(2) . . ? N2 C8 C7 115.57(19) . . ? C9 C8 C7 122.2(2) . . ? N2 C12 C11 122.6(2) . . ? N1 C7 C8 109.96(18) . . ? C1 N1 C7 111.80(17) . . ? C1 N1 C13 110.23(16) . . ? C7 N1 C13 111.30(17) . . ? C1 N1 Mn1 115.86(14) . . ? C7 N1 Mn1 103.51(13) . . ? C13 N1 Mn1 103.74(13) . . ? N1 C13 C14 108.68(19) . . ? C20 N4 C24 117.8(2) . . ? N3 C18 C17 121.9(3) . . ? C2 C1 C6 119.4(2) . . ? C2 C1 N1 120.6(2) . . ? C6 C1 N1 119.9(2) . . ? N3 C14 C15 122.4(2) . . ? N3 C14 C13 116.3(2) . . ? C15 C14 C13 121.3(2) . . ? C4 C3 C2 121.1(2) . . ? N4 C20 C21 121.6(2) . . ? N4 C20 C19 115.7(2) . . ? C21 C20 C19 122.7(2) . . ? C6 C5 C4 121.3(2) . . ? C4 C19 C20 114.80(19) . . ? C22 C21 C20 120.0(2) . . ? N4 C24 C23 123.6(3) . . ? C22 C23 C24 118.1(2) . . ? C14 C15 C16 118.3(3) . . ? C5 C6 C1 120.1(2) . . ? C17 C16 C15 119.3(3) . . ? C16 C17 C18 119.2(3) . . ? C23 C22 C21 118.9(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.639 _refine_diff_density_min -0.728 _refine_diff_density_rms 0.149 # Attachment 'structure__3_.cif' data_c:\gaelle~1\articl~2\struct~2\(3)-cu~1\gr3 _database_code_depnum_ccdc_archive 'CCDC 649298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; none ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety 'C24 H22 Cl2.03 Cu N4 O2.79' _chemical_formula_sum 'C24 H22 Cl2.03 Cu N4 O2.79' _chemical_formula_weight 549.55 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 '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 9.4866(3) _cell_length_b 12.7984(5) _cell_length_c 13.0868(5) _cell_angle_alpha 98.379(2) _cell_angle_beta 104.084(2) _cell_angle_gamma 91.693(2) _cell_volume 1521.20(10) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 27.0 _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.922 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 16464 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.61 _diffrn_reflns_theta_max 27.01 _reflns_number_total 6426 _reflns_number_gt 5595 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.1404P)^2^+16.5972P] 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 constr _refine_ls_extinction_method none _refine_ls_number_reflns 6426 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1681 _refine_ls_R_factor_gt 0.1534 _refine_ls_wR_factor_ref 0.3674 _refine_ls_wR_factor_gt 0.3578 _refine_ls_goodness_of_fit_ref 1.208 _refine_ls_restrained_S_all 1.208 _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 0.17223(12) 0.24496(8) 0.33187(8) 0.0273(4) Uani 1 1 d . . . N2 N 0.2487(9) 0.3971(6) 0.3808(6) 0.0333(18) Uani 1 1 d . A . N3 N 0.1056(9) 0.1053(6) 0.2392(7) 0.039(2) Uani 1 1 d . A . N1 N 0.2731(8) 0.2630(6) 0.2124(6) 0.0291(16) Uani 1 1 d . A . C2 C 0.0349(10) 0.3191(6) 0.1214(7) 0.0290(18) Uani 1 1 d . A . H2 H -0.0006 0.3081 0.1811 0.035 Uiso 1 1 calc R . . N4 N -0.0981(12) 0.2666(8) -0.3048(7) 0.056(3) Uani 1 1 d . . . C1 C 0.1756(9) 0.3019(6) 0.1209(6) 0.0237(16) Uani 1 1 d . . . C8 C 0.3554(10) 0.4235(7) 0.3363(7) 0.033(2) Uani 1 1 d . . . C3 C -0.0578(11) 0.3534(7) 0.0329(7) 0.033(2) Uani 1 1 d . . . H3 H -0.1562 0.3652 0.0327 0.039 Uiso 1 1 calc R A . C6 C 0.2282(11) 0.3195(8) 0.0351(7) 0.036(2) Uani 1 1 d . A . H6 H 0.3266 0.3078 0.0352 0.044 Uiso 1 1 calc R . . C4 C -0.0056(12) 0.3699(7) -0.0541(7) 0.038(2) Uani 1 1 d . A . C14 C 0.1874(12) 0.0776(7) 0.1717(8) 0.042(3) Uani 1 1 d . . . C9 C 0.4214(13) 0.5263(8) 0.3615(8) 0.048(3) Uani 1 1 d . A . H9 H 0.4946 0.5461 0.3284 0.057 Uiso 1 1 calc R . . C21 C -0.2914(12) 0.2494(8) -0.2288(8) 0.040(2) Uani 1 1 d . . . H21 H -0.3418 0.2751 -0.1768 0.048 Uiso 1 1 calc R . . C20 C -0.1697(12) 0.3032(7) -0.2308(8) 0.039(2) Uani 1 1 d . A . C24 C -0.1487(15) 0.1736(10) -0.3767(9) 0.054(3) Uani 1 1 d . . . H24 H -0.0978 0.1474 -0.4282 0.064 Uiso 1 1 calc R . . C18 C -0.0106(13) 0.0406(8) 0.2404(10) 0.055(3) Uani 1 1 d . . . H18 H -0.0690 0.0613 0.2884 0.066 Uiso 1 1 calc R A . C5 C 0.1362(13) 0.3548(8) -0.0520(8) 0.042(2) Uani 1 1 d . . . H5 H 0.1732 0.3684 -0.1103 0.050 Uiso 1 1 calc R A . C7 C 0.4008(10) 0.3379(8) 0.2652(8) 0.037(2) Uani 1 1 d . A . H7B H 0.4791 0.3005 0.3071 0.045 Uiso 1 1 calc R . . H7A H 0.4389 0.3679 0.2108 0.045 Uiso 1 1 calc R . . C23 C -0.2743(16) 0.1210(9) -0.3708(10) 0.058(4) Uani 1 1 d . . . H23 H -0.3106 0.0572 -0.4182 0.070 Uiso 1 1 calc R . . C17 C -0.0440(19) -0.0548(10) 0.1723(15) 0.089(7) Uani 1 1 d . A . H17 H -0.1244 -0.1003 0.1736 0.106 Uiso 1 1 calc R . . C12 C 0.2059(13) 0.4665(10) 0.4503(8) 0.050(3) Uani 1 1 d . . . H12 H 0.1298 0.4464 0.4806 0.060 Uiso 1 1 calc R A . C13 C 0.3151(12) 0.1537(8) 0.1786(9) 0.042(2) Uani 1 1 d . A . H13B H 0.4020 0.1367 0.2313 0.050 Uiso 1 1 calc R . . H13A H 0.3383 0.1489 0.1083 0.050 Uiso 1 1 calc R . . C19 C -0.1073(15) 0.3998(7) -0.1528(8) 0.051(3) Uani 1 1 d . . . H19A H -0.1871 0.4391 -0.1323 0.061 Uiso 1 1 calc R A . H19B H -0.0531 0.4465 -0.1862 0.061 Uiso 1 1 calc R . . C22 C -0.3464(14) 0.1598(10) -0.2976(10) 0.055(3) Uani 1 1 d . . . H22 H -0.4345 0.1247 -0.2945 0.066 Uiso 1 1 calc R . . C11 C 0.2711(18) 0.5685(9) 0.4794(9) 0.069(5) Uani 1 1 d . A . H11 H 0.2411 0.6179 0.5302 0.083 Uiso 1 1 calc R . . C10 C 0.3794(17) 0.5972(8) 0.4339(10) 0.062(4) Uani 1 1 d . . . H10 H 0.4250 0.6668 0.4532 0.075 Uiso 1 1 calc R A . C15 C 0.1596(16) -0.0176(9) 0.1030(9) 0.059(4) Uani 1 1 d . A . H15 H 0.2209 -0.0375 0.0569 0.071 Uiso 1 1 calc R . . C16 C 0.0417(18) -0.0831(9) 0.1023(13) 0.068(4) Uani 1 1 d . . . H16 H 0.0192 -0.1477 0.0538 0.081 Uiso 1 1 calc R A . Cl1B Cl -0.0051(5) 0.2491(4) 0.4169(3) 0.0828(12) Uani 1 1 d . A . Cl1A Cl 0.3856(6) 0.1627(4) 0.4440(5) 0.0432(13) Uani 0.70 1 d P A 2 O1 O 0.1392(17) 0.0419(9) -0.4471(10) 0.071(4) Uani 0.74 1 d P . . O2 O 0.634(2) 0.0605(17) 0.3396(15) 0.084(6) Uani 0.55 1 d P . . O3 O -0.391(2) 0.4449(15) 0.0960(15) 0.037(4) Uiso 0.35 1 d P . . O4 O -0.472(3) 0.431(2) -0.080(2) 0.062(6) Uiso 0.35 1 d P . . O5 O 0.225(3) 0.526(2) -0.247(2) 0.080(7) Uiso 0.44 1 d P . . Cl2A Cl 0.3491(15) 0.1886(11) 0.4781(10) 0.043(3) Uani 0.30 1 d P A 1 O6 O 0.126(4) 0.387(3) -0.322(3) 0.062(8) Uiso 0.28 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 0.0285(6) 0.0242(6) 0.0260(5) 0.0123(4) -0.0034(4) -0.0067(4) N2 0.041(4) 0.027(4) 0.025(4) 0.010(3) -0.009(3) 0.002(3) N3 0.041(5) 0.017(3) 0.045(5) 0.014(3) -0.019(4) -0.007(3) N1 0.019(3) 0.028(4) 0.034(4) 0.002(3) -0.003(3) 0.001(3) C2 0.043(5) 0.021(4) 0.025(4) 0.006(3) 0.011(4) 0.009(4) N4 0.072(7) 0.051(6) 0.037(5) 0.019(4) -0.009(5) 0.000(5) C1 0.030(4) 0.015(4) 0.024(4) 0.004(3) 0.003(3) -0.002(3) C8 0.030(5) 0.032(5) 0.027(4) 0.012(4) -0.016(4) -0.011(4) C3 0.039(5) 0.023(4) 0.032(5) 0.007(3) 0.000(4) 0.009(4) C6 0.030(5) 0.044(5) 0.034(5) 0.005(4) 0.008(4) -0.005(4) C4 0.060(7) 0.022(4) 0.026(4) 0.009(3) -0.003(4) -0.001(4) C14 0.054(6) 0.018(4) 0.042(5) 0.012(4) -0.015(5) 0.015(4) C9 0.051(6) 0.032(5) 0.043(6) 0.018(4) -0.026(5) -0.014(5) C21 0.046(6) 0.043(6) 0.034(5) 0.022(4) 0.004(4) 0.008(5) C20 0.052(6) 0.029(5) 0.030(5) 0.012(4) -0.006(4) 0.006(4) C24 0.077(9) 0.052(7) 0.033(5) 0.015(5) 0.010(5) 0.019(6) C18 0.050(7) 0.033(5) 0.070(8) 0.029(5) -0.020(6) -0.013(5) C5 0.056(7) 0.040(5) 0.029(5) 0.007(4) 0.008(4) -0.012(5) C7 0.018(4) 0.050(6) 0.039(5) 0.010(4) -0.001(4) -0.011(4) C23 0.076(9) 0.034(5) 0.047(6) 0.012(5) -0.020(6) -0.001(6) C17 0.088(11) 0.034(6) 0.109(13) 0.043(8) -0.057(10) -0.029(7) C12 0.052(7) 0.062(7) 0.032(5) 0.007(5) 0.002(5) 0.022(6) C13 0.045(6) 0.031(5) 0.046(6) -0.001(4) 0.008(5) 0.016(4) C19 0.086(9) 0.021(4) 0.031(5) 0.008(4) -0.015(5) 0.004(5) C22 0.054(7) 0.054(7) 0.053(7) 0.033(6) -0.008(6) -0.009(6) C11 0.106(12) 0.035(6) 0.036(6) -0.016(5) -0.033(7) 0.035(7) C10 0.082(10) 0.026(5) 0.050(7) 0.014(5) -0.039(7) -0.006(6) C15 0.082(9) 0.032(5) 0.045(6) 0.006(5) -0.021(6) 0.018(6) C16 0.081(10) 0.021(5) 0.076(9) 0.012(5) -0.031(8) 0.001(6) Cl1B 0.079(3) 0.107(3) 0.072(2) 0.017(2) 0.041(2) -0.021(2) Cl1A 0.041(3) 0.029(3) 0.049(3) 0.016(2) -0.017(2) -0.0031(18) O1 0.116(11) 0.054(7) 0.068(8) 0.030(6) 0.057(8) 0.038(7) O2 0.063(11) 0.121(16) 0.078(12) 0.067(12) 0.004(9) 0.021(11) Cl2A 0.048(7) 0.037(7) 0.034(6) 0.019(5) -0.016(5) -0.003(5) _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 1.999(8) . ? Cu1 N2 2.013(7) . ? Cu1 N1 2.057(8) . ? Cu1 Cl1B 2.229(4) . ? Cu1 Cl2A 2.430(12) . ? Cu1 Cl1A 2.547(5) . ? N2 C12 1.322(14) . ? N2 C8 1.342(13) . ? N3 C14 1.330(15) . ? N3 C18 1.363(14) . ? N1 C7 1.482(11) . ? N1 C1 1.483(10) . ? N1 C13 1.500(12) . ? C2 C1 1.361(13) . ? C2 C3 1.408(12) . ? N4 C20 1.351(16) . ? N4 C24 1.398(15) . ? C1 C6 1.378(12) . ? C8 C9 1.399(12) . ? C8 C7 1.476(15) . ? C3 C4 1.387(14) . ? C6 C5 1.398(14) . ? C4 C5 1.359(16) . ? C4 C19 1.518(13) . ? C14 C15 1.382(14) . ? C14 C13 1.508(16) . ? C9 C10 1.354(19) . ? C21 C20 1.335(15) . ? C21 C22 1.353(16) . ? C20 C19 1.488(13) . ? C24 C23 1.375(19) . ? C18 C17 1.38(2) . ? C23 C22 1.35(2) . ? C17 C16 1.38(2) . ? C12 C11 1.387(18) . ? C11 C10 1.37(2) . ? C15 C16 1.37(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 N2 161.5(3) . . ? N3 Cu1 N1 81.5(3) . . ? N2 Cu1 N1 81.2(3) . . ? N3 Cu1 Cl1B 96.4(3) . . ? N2 Cu1 Cl1B 97.2(3) . . ? N1 Cu1 Cl1B 157.9(2) . . ? N3 Cu1 Cl2A 100.2(4) . . ? N2 Cu1 Cl2A 91.4(4) . . ? N1 Cu1 Cl2A 108.4(4) . . ? Cl1B Cu1 Cl2A 93.6(4) . . ? N3 Cu1 Cl1A 90.8(3) . . ? N2 Cu1 Cl1A 97.0(2) . . ? N1 Cu1 Cl1A 94.9(2) . . ? Cl1B Cu1 Cl1A 107.11(19) . . ? Cl2A Cu1 Cl1A 15.6(3) . . ? C12 N2 C8 121.0(9) . . ? C12 N2 Cu1 126.5(8) . . ? C8 N2 Cu1 112.5(6) . . ? C14 N3 C18 120.3(10) . . ? C14 N3 Cu1 113.2(7) . . ? C18 N3 Cu1 126.5(9) . . ? C7 N1 C1 112.4(7) . . ? C7 N1 C13 112.7(8) . . ? C1 N1 C13 110.3(7) . . ? C7 N1 Cu1 104.5(5) . . ? C1 N1 Cu1 112.7(5) . . ? C13 N1 Cu1 103.9(6) . . ? C1 C2 C3 119.7(8) . . ? C20 N4 C24 120.9(11) . . ? C2 C1 C6 120.3(8) . . ? C2 C1 N1 120.1(7) . . ? C6 C1 N1 119.6(8) . . ? N2 C8 C9 120.2(10) . . ? N2 C8 C7 116.3(8) . . ? C9 C8 C7 123.4(10) . . ? C4 C3 C2 120.1(9) . . ? C1 C6 C5 119.8(9) . . ? C5 C4 C3 119.4(9) . . ? C5 C4 C19 120.2(10) . . ? C3 C4 C19 120.4(10) . . ? N3 C14 C15 121.3(11) . . ? N3 C14 C13 116.0(8) . . ? C15 C14 C13 122.6(12) . . ? C10 C9 C8 119.0(12) . . ? C20 C21 C22 123.0(11) . . ? C21 C20 N4 118.5(10) . . ? C21 C20 C19 122.7(11) . . ? N4 C20 C19 118.8(11) . . ? C23 C24 N4 118.2(12) . . ? N3 C18 C17 120.6(15) . . ? C4 C5 C6 120.7(9) . . ? C8 C7 N1 108.7(7) . . ? C22 C23 C24 120.2(11) . . ? C18 C17 C16 118.8(14) . . ? N2 C12 C11 120.6(13) . . ? N1 C13 C14 107.4(8) . . ? C20 C19 C4 110.4(8) . . ? C21 C22 C23 119.2(11) . . ? C10 C11 C12 119.2(11) . . ? C9 C10 C11 120.0(10) . . ? C16 C15 C14 119.0(14) . . ? C15 C16 C17 119.9(12) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 1.749 _refine_diff_density_min -1.347 _refine_diff_density_rms 0.185 # Attachment 'structure__4_.cif' data_c:\gaelle~1\articl~2\struct~2\(4)-co~1\ann2 _database_code_depnum_ccdc_archive 'CCDC 649299' _audit_creation_method SHELXL-97 _chemical_name_systematic ; none ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety '[Co(tpma)(NO3)2]' _chemical_formula_sum 'C24 H22 Co N6 O6' _chemical_formula_weight 549.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3562(2) _cell_length_b 10.2179(2) _cell_length_c 13.8837(4) _cell_angle_alpha 101.0790(10) _cell_angle_beta 96.1500(10) _cell_angle_gamma 110.0150(10) _cell_volume 1202.18(5) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 28.3 _exptl_crystal_description plates _exptl_crystal_colour red _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 566 _exptl_absorpt_coefficient_mu 0.767 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 23407 _diffrn_reflns_av_R_equivalents 0.0826 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 28.26 _reflns_number_total 5910 _reflns_number_gt 4121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0368P)^2^+0.0586P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5910 _refine_ls_number_parameters 334 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0889 _refine_ls_wR_factor_gt 0.0803 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 Co1 Co 0.34935(3) 0.26590(2) 0.271611(19) 0.01950(9) Uani 1 1 d . . . O1A O 0.35262(15) 0.40596(13) 0.40353(10) 0.0257(3) Uani 1 1 d . . . N1B N 0.24466(19) 0.42933(16) 0.14937(13) 0.0261(4) Uani 1 1 d . . . O1B O 0.25035(16) 0.30419(13) 0.14401(10) 0.0280(3) Uani 1 1 d . . . N2 N 0.25766(17) 0.04887(15) 0.20086(11) 0.0196(3) Uani 1 1 d . . . O2A O 0.13069(15) 0.24548(13) 0.33006(10) 0.0276(3) Uani 1 1 d . . . N1A N 0.20706(19) 0.35205(17) 0.40260(12) 0.0272(4) Uani 1 1 d . . . O3A O 0.14743(18) 0.40004(17) 0.46776(11) 0.0417(4) Uani 1 1 d . . . O3B O 0.1880(2) 0.45337(15) 0.07374(11) 0.0447(4) Uani 1 1 d . . . N3 N 0.57694(17) 0.35202(15) 0.25368(11) 0.0214(4) Uani 1 1 d . . . C5 C 0.1880(2) -0.00384(19) 0.52668(14) 0.0235(4) Uani 1 1 d . . . H5 H 0.1056 -0.0929 0.5199 0.028 Uiso 1 1 calc R . . C20 C 0.2183(2) 0.0939(2) 0.78976(14) 0.0240(4) Uani 1 1 d . . . C12 C 0.1289(2) -0.01007(19) 0.12972(14) 0.0223(4) Uani 1 1 d . . . H12 H 0.0803 0.0509 0.1100 0.027 Uiso 1 1 calc R . . C6 C 0.2743(2) 0.0139(2) 0.45145(14) 0.0241(4) Uani 1 1 d . . . H6 H 0.2503 -0.0632 0.3942 0.029 Uiso 1 1 calc R . . N1 N 0.47442(17) 0.16870(16) 0.37556(12) 0.0221(4) Uani 1 1 d . . . C14 C 0.6867(2) 0.34105(19) 0.31903(14) 0.0225(4) Uani 1 1 d . . . C4 C 0.2199(2) 0.10609(19) 0.61154(14) 0.0227(4) Uani 1 1 d . . . C1 C 0.3956(2) 0.14319(19) 0.45874(14) 0.0213(4) Uani 1 1 d . . . O2B O 0.2957(2) 0.51907(15) 0.22997(11) 0.0475(5) Uani 1 1 d . . . C18 C 0.6222(2) 0.41962(19) 0.18118(14) 0.0258(4) Uani 1 1 d . . . H18 H 0.5454 0.4289 0.1353 0.031 Uiso 1 1 calc R . . C8 C 0.3268(2) -0.03700(19) 0.22947(14) 0.0216(4) Uani 1 1 d . . . C21 C 0.2013(2) -0.0314(2) 0.82094(15) 0.0280(5) Uani 1 1 d . . . H21 H 0.1294 -0.1217 0.7818 0.034 Uiso 1 1 calc R . . N4 N 0.3205(2) 0.22316(18) 0.84245(13) 0.0335(4) Uani 1 1 d . . . C13 C 0.6338(2) 0.2779(2) 0.40427(16) 0.0299(5) Uani 1 1 d . . . H13B H 0.7054 0.2333 0.4274 0.036 Uiso 1 1 calc R . . H13A H 0.6378 0.3559 0.4606 0.036 Uiso 1 1 calc R . . C15 C 0.8412(2) 0.3940(2) 0.31274(15) 0.0270(5) Uani 1 1 d . . . H15 H 0.9164 0.3839 0.3594 0.032 Uiso 1 1 calc R . . C2 C 0.4308(2) 0.2513(2) 0.54588(15) 0.0269(5) Uani 1 1 d . . . H2 H 0.5159 0.3391 0.5544 0.032 Uiso 1 1 calc R . . C11 C 0.0642(2) -0.1547(2) 0.08420(15) 0.0263(4) Uani 1 1 d . . . H11 H -0.0277 -0.1933 0.0348 0.032 Uiso 1 1 calc R . . C9 C 0.2692(2) -0.1833(2) 0.18578(16) 0.0288(5) Uani 1 1 d . . . H9 H 0.3201 -0.2424 0.2060 0.035 Uiso 1 1 calc R . . C19 C 0.1248(2) 0.0906(2) 0.69341(15) 0.0269(4) Uani 1 1 d . . . H19A H 0.0854 0.1697 0.7048 0.032 Uiso 1 1 calc R . . H19B H 0.0345 -0.0013 0.6716 0.032 Uiso 1 1 calc R . . C7 C 0.4717(2) 0.0358(2) 0.30784(15) 0.0251(4) Uani 1 1 d . . . H7B H 0.4810 -0.0320 0.3481 0.030 Uiso 1 1 calc R . . H7A H 0.5624 0.0604 0.2746 0.030 Uiso 1 1 calc R . . C10 C 0.1373(3) -0.2421(2) 0.11266(16) 0.0307(5) Uani 1 1 d . . . H10 H 0.0968 -0.3421 0.0820 0.037 Uiso 1 1 calc R . . C3 C 0.3439(2) 0.2327(2) 0.61986(15) 0.0279(5) Uani 1 1 d . . . H3 H 0.3696 0.3087 0.6780 0.033 Uiso 1 1 calc R . . C23 C 0.3955(3) 0.1103(3) 0.96424(16) 0.0391(6) Uani 1 1 d . . . H23 H 0.4586 0.1199 1.0255 0.047 Uiso 1 1 calc R . . C17 C 0.7738(2) 0.4754(2) 0.17100(16) 0.0321(5) Uani 1 1 d . . . H17 H 0.8015 0.5224 0.1192 0.038 Uiso 1 1 calc R . . C16 C 0.8856(2) 0.4619(2) 0.23765(16) 0.0317(5) Uani 1 1 d . . . H16 H 0.9915 0.4987 0.2320 0.038 Uiso 1 1 calc R . . C22 C 0.2911(2) -0.0223(2) 0.91005(16) 0.0352(5) Uani 1 1 d . . . H22 H 0.2809 -0.1061 0.9333 0.042 Uiso 1 1 calc R . . C24 C 0.4060(3) 0.2287(3) 0.92730(16) 0.0406(6) Uani 1 1 d . . . H24 H 0.4786 0.3198 0.9647 0.049 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 Co1 0.01834(15) 0.01522(14) 0.02427(16) 0.00611(10) 0.00143(11) 0.00551(10) O1A 0.0218(8) 0.0195(7) 0.0317(8) 0.0049(6) -0.0029(6) 0.0057(6) N1B 0.0294(10) 0.0181(8) 0.0305(10) 0.0073(7) 0.0001(8) 0.0092(7) O1B 0.0368(8) 0.0185(7) 0.0313(8) 0.0070(6) -0.0005(6) 0.0149(6) N2 0.0209(8) 0.0171(8) 0.0251(9) 0.0086(7) 0.0084(7) 0.0092(6) O2A 0.0233(7) 0.0197(7) 0.0321(8) -0.0035(6) 0.0009(6) 0.0053(6) N1A 0.0273(10) 0.0250(9) 0.0302(10) 0.0034(8) 0.0000(8) 0.0144(8) O3A 0.0397(9) 0.0526(10) 0.0343(9) -0.0070(7) 0.0044(7) 0.0293(8) O3B 0.0697(12) 0.0303(8) 0.0345(9) 0.0097(7) -0.0132(8) 0.0249(8) N3 0.0213(9) 0.0177(8) 0.0242(9) 0.0079(7) 0.0040(7) 0.0047(6) C5 0.0195(10) 0.0209(10) 0.0277(11) 0.0107(8) 0.0009(9) 0.0030(8) C20 0.0238(11) 0.0270(10) 0.0250(11) 0.0077(8) 0.0112(9) 0.0115(8) C12 0.0238(11) 0.0199(10) 0.0256(11) 0.0072(8) 0.0092(9) 0.0089(8) C6 0.0224(10) 0.0234(10) 0.0237(11) 0.0088(8) 0.0007(8) 0.0044(8) N1 0.0178(8) 0.0235(8) 0.0258(9) 0.0116(7) 0.0039(7) 0.0058(7) C14 0.0203(10) 0.0184(9) 0.0273(11) 0.0068(8) 0.0032(8) 0.0051(8) C4 0.0217(10) 0.0240(10) 0.0256(11) 0.0125(8) 0.0028(8) 0.0095(8) C1 0.0199(10) 0.0227(10) 0.0256(11) 0.0140(8) 0.0030(8) 0.0091(8) O2B 0.0791(13) 0.0203(8) 0.0347(9) 0.0000(7) -0.0116(9) 0.0184(8) C18 0.0306(12) 0.0225(10) 0.0255(11) 0.0098(8) 0.0056(9) 0.0093(8) C8 0.0261(11) 0.0224(10) 0.0259(11) 0.0126(8) 0.0151(9) 0.0142(8) C21 0.0259(11) 0.0314(11) 0.0311(12) 0.0101(9) 0.0114(9) 0.0129(9) N4 0.0384(11) 0.0307(10) 0.0291(10) 0.0060(8) 0.0047(8) 0.0115(8) C13 0.0167(10) 0.0381(12) 0.0324(12) 0.0186(10) 0.0003(9) 0.0029(9) C15 0.0210(11) 0.0271(10) 0.0328(12) 0.0086(9) 0.0054(9) 0.0079(8) C2 0.0254(11) 0.0178(9) 0.0347(12) 0.0095(8) 0.0054(9) 0.0030(8) C11 0.0269(11) 0.0200(10) 0.0279(11) 0.0030(8) 0.0092(9) 0.0038(8) C9 0.0405(13) 0.0212(10) 0.0360(12) 0.0131(9) 0.0189(10) 0.0185(9) C19 0.0242(11) 0.0281(10) 0.0302(11) 0.0102(9) 0.0062(9) 0.0101(9) C7 0.0247(11) 0.0260(10) 0.0358(12) 0.0171(9) 0.0118(9) 0.0163(8) C10 0.0438(13) 0.0159(10) 0.0327(12) 0.0046(9) 0.0176(11) 0.0093(9) C3 0.0328(12) 0.0211(10) 0.0295(12) 0.0067(8) 0.0072(9) 0.0090(9) C23 0.0370(13) 0.0611(16) 0.0229(12) 0.0117(11) 0.0050(10) 0.0224(12) C17 0.0349(13) 0.0319(11) 0.0352(13) 0.0173(9) 0.0172(10) 0.0115(9) C16 0.0238(11) 0.0304(11) 0.0422(13) 0.0115(10) 0.0140(10) 0.0080(9) C22 0.0347(13) 0.0476(14) 0.0397(14) 0.0246(11) 0.0195(11) 0.0244(11) C24 0.0421(14) 0.0432(13) 0.0278(13) 0.0026(10) 0.0002(11) 0.0105(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Co1 N3 2.0702(15) . ? Co1 N2 2.0734(14) . ? Co1 O1B 2.0765(13) . ? Co1 O1A 2.0867(13) . ? Co1 O2A 2.2396(13) . ? Co1 N1 2.3288(15) . ? O1A N1A 1.280(2) . ? N1B O3B 1.230(2) . ? N1B O2B 1.230(2) . ? N1B O1B 1.2862(19) . ? N2 C12 1.345(2) . ? N2 C8 1.347(2) . ? O2A N1A 1.266(2) . ? N1A O3A 1.223(2) . ? N3 C14 1.345(2) . ? N3 C18 1.352(2) . ? C5 C4 1.388(3) . ? C5 C6 1.389(3) . ? C20 N4 1.344(2) . ? C20 C21 1.394(3) . ? C20 C19 1.506(3) . ? C12 C11 1.377(3) . ? C6 C1 1.393(2) . ? N1 C1 1.453(2) . ? N1 C13 1.480(2) . ? N1 C7 1.486(2) . ? C14 C15 1.379(3) . ? C14 C13 1.504(3) . ? C4 C3 1.385(3) . ? C4 C19 1.516(3) . ? C1 C2 1.394(3) . ? C18 C17 1.370(3) . ? C8 C9 1.387(3) . ? C8 C7 1.502(3) . ? C21 C22 1.387(3) . ? N4 C24 1.331(3) . ? C15 C16 1.384(3) . ? C2 C3 1.379(3) . ? C11 C10 1.385(3) . ? C9 C10 1.380(3) . ? C23 C22 1.379(3) . ? C23 C24 1.381(3) . ? C17 C16 1.382(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 Co1 N2 109.00(6) . . ? N3 Co1 O1B 96.62(6) . . ? N2 Co1 O1B 88.17(5) . . ? N3 Co1 O1A 101.24(6) . . ? N2 Co1 O1A 140.40(6) . . ? O1B Co1 O1A 113.48(5) . . ? N3 Co1 O2A 160.14(5) . . ? N2 Co1 O2A 90.34(5) . . ? O1B Co1 O2A 88.23(5) . . ? O1A Co1 O2A 59.41(5) . . ? N3 Co1 N1 77.54(6) . . ? N2 Co1 N1 77.31(6) . . ? O1B Co1 N1 161.35(5) . . ? O1A Co1 N1 85.12(5) . . ? O2A Co1 N1 103.30(5) . . ? N1A O1A Co1 96.10(10) . . ? O3B N1B O2B 123.15(16) . . ? O3B N1B O1B 118.45(15) . . ? O2B N1B O1B 118.40(16) . . ? N1B O1B Co1 118.08(11) . . ? C12 N2 C8 118.80(15) . . ? C12 N2 Co1 122.43(12) . . ? C8 N2 Co1 118.73(12) . . ? N1A O2A Co1 89.41(10) . . ? O3A N1A O2A 122.92(17) . . ? O3A N1A O1A 122.01(16) . . ? O2A N1A O1A 115.07(15) . . ? C14 N3 C18 118.07(16) . . ? C14 N3 Co1 117.75(12) . . ? C18 N3 Co1 124.18(13) . . ? C4 C5 C6 121.23(17) . . ? N4 C20 C21 122.16(19) . . ? N4 C20 C19 116.50(17) . . ? C21 C20 C19 121.33(17) . . ? N2 C12 C11 123.03(17) . . ? C5 C6 C1 120.92(18) . . ? C1 N1 C13 114.62(15) . . ? C1 N1 C7 113.89(14) . . ? C13 N1 C7 110.47(15) . . ? C1 N1 Co1 110.39(11) . . ? C13 N1 Co1 102.69(11) . . ? C7 N1 Co1 103.63(11) . . ? N3 C14 C15 122.03(18) . . ? N3 C14 C13 116.46(16) . . ? C15 C14 C13 121.35(17) . . ? C3 C4 C5 117.57(18) . . ? C3 C4 C19 120.23(17) . . ? C5 C4 C19 122.20(16) . . ? C6 C1 C2 117.53(18) . . ? C6 C1 N1 121.24(17) . . ? C2 C1 N1 121.05(16) . . ? N3 C18 C17 122.92(19) . . ? N2 C8 C9 121.23(18) . . ? N2 C8 C7 116.15(15) . . ? C9 C8 C7 122.58(17) . . ? C22 C21 C20 118.94(19) . . ? C24 N4 C20 117.69(19) . . ? N1 C13 C14 112.18(16) . . ? C14 C15 C16 119.22(19) . . ? C3 C2 C1 120.98(18) . . ? C12 C11 C10 117.91(19) . . ? C10 C9 C8 119.28(18) . . ? C20 C19 C4 111.83(16) . . ? N1 C7 C8 113.05(14) . . ? C9 C10 C11 119.72(17) . . ? C2 C3 C4 121.69(19) . . ? C22 C23 C24 118.4(2) . . ? C18 C17 C16 118.62(19) . . ? C17 C16 C15 119.14(19) . . ? C23 C22 C21 118.9(2) . . ? N4 C24 C23 124.0(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.417 _refine_diff_density_min -0.439 _refine_diff_density_rms 0.065 # Attachment 'structure__5_.cif' data_c:\gaelle~1\articl~2\struct~2\(5)-cu~1\gr2 _database_code_depnum_ccdc_archive 'CCDC 649300' _audit_creation_method SHELXL-97 _chemical_name_systematic ; none ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety '[Cu(tpma-H)(NO32](NO3)' _chemical_formula_sum 'C24 H23 Cu N7 O9' _chemical_formula_weight 617.03 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 8.0308(16) _cell_length_b 8.6296(17) _cell_length_c 20.091(4) _cell_angle_alpha 93.94(3) _cell_angle_beta 92.29(3) _cell_angle_gamma 116.16(3) _cell_volume 1242.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25.1 _exptl_crystal_description plates _exptl_crystal_colour green _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 634 _exptl_absorpt_coefficient_mu 0.949 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 9603 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 25.13 _reflns_number_total 4392 _reflns_number_gt 4139 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4392 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0692 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1920 _refine_ls_wR_factor_gt 0.1884 _refine_ls_goodness_of_fit_ref 1.411 _refine_ls_restrained_S_all 1.411 _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 0.25191(6) 0.66051(6) 0.84418(3) 0.0171(2) Uani 1 1 d . . . N2 N 0.2527(5) 0.8566(5) 0.80131(18) 0.0189(8) Uani 1 1 d . . . O2A O 0.1648(5) 0.4567(5) 0.7409(2) 0.0430(10) Uani 1 1 d . . . O1B O 0.3332(6) 0.8370(6) 0.9464(2) 0.0466(11) Uani 1 1 d . . . C4 C 0.6633(6) 0.6184(6) 0.6355(2) 0.0204(9) Uani 1 1 d . . . N1 N 0.5453(5) 0.7845(4) 0.82496(17) 0.0156(7) Uani 1 1 d . . . O3A O -0.1253(4) 0.2678(4) 0.72935(17) 0.0305(8) Uani 1 1 d . . . N1B N 0.1778(5) 0.8035(5) 0.96505(19) 0.0217(8) Uani 1 1 d . . . N3 N 0.3223(5) 0.5004(5) 0.88838(18) 0.0207(8) Uani 1 1 d . . . N1A N 0.0030(6) 0.3963(5) 0.7594(2) 0.0278(9) Uani 1 1 d . . . O3B O 0.1654(6) 0.8697(5) 1.01944(19) 0.0446(10) Uani 1 1 d . . . C14 C 0.5072(6) 0.5540(5) 0.8983(2) 0.0168(9) Uani 1 1 d . . . C6 C 0.5841(7) 0.8141(6) 0.7040(2) 0.0263(11) Uani 1 1 d . . . H2 H 0.5556 0.9100 0.7072 0.032 Uiso 1 1 calc R . . C1 C 0.5832(5) 0.7278(5) 0.7607(2) 0.0168(9) Uani 1 1 d . . . C8 C 0.4211(6) 0.9905(6) 0.8005(2) 0.0170(9) Uani 1 1 d . . . C7 C 0.5826(6) 0.9707(5) 0.8317(2) 0.0175(9) Uani 1 1 d . . . H7A H 0.6965 1.0403 0.8096 0.021 Uiso 1 1 calc R . . H7B H 0.6036 1.0143 0.8797 0.021 Uiso 1 1 calc R . . C16 C 0.4556(7) 0.2858(6) 0.9414(2) 0.0249(10) Uani 1 1 d . . . H16 H 0.5009 0.2110 0.9590 0.030 Uiso 1 1 calc R . . C18 C 0.2045(7) 0.3446(6) 0.9060(2) 0.0242(10) Uani 1 1 d . . . H18 H 0.0745 0.3095 0.9001 0.029 Uiso 1 1 calc R . . O2C O 1.3843(6) 0.9537(6) 0.5895(2) 0.0534(12) Uani 1 1 d . . . C2 C 0.6180(6) 0.5848(6) 0.7529(2) 0.0204(9) Uani 1 1 d . . . H6 H 0.6146 0.5219 0.7902 0.025 Uiso 1 1 calc R . . C10 C 0.2873(6) 1.1510(6) 0.7446(2) 0.0246(10) Uani 1 1 d . . . H10 H 0.2998 1.2528 0.7255 0.030 Uiso 1 1 calc R . . O1A O -0.0232(6) 0.4743(5) 0.8107(2) 0.0422(10) Uani 1 1 d . . . C5 C 0.6267(6) 0.7597(6) 0.6429(2) 0.0233(10) Uani 1 1 d . . . H3 H 0.6306 0.8219 0.6054 0.028 Uiso 1 1 calc R . . C13 C 0.6302(6) 0.7374(5) 0.8826(2) 0.0182(9) Uani 1 1 d . . . H13B H 0.6486 0.8192 0.9224 0.022 Uiso 1 1 calc R . . H13A H 0.7536 0.7473 0.8719 0.022 Uiso 1 1 calc R . . C9 C 0.4430(6) 1.1397(6) 0.7722(2) 0.0215(9) Uani 1 1 d . . . H9 H 0.5633 1.2336 0.7716 0.026 Uiso 1 1 calc R . . O1C O 1.1122(6) 0.9516(6) 0.5820(2) 0.0535(12) Uani 1 1 d . . . C15 C 0.5785(6) 0.4483(6) 0.9242(2) 0.0205(9) Uani 1 1 d . . . H15 H 0.7091 0.4866 0.9301 0.025 Uiso 1 1 calc R . . C20 C 0.8317(6) 0.4760(6) 0.5733(2) 0.0228(10) Uani 1 1 d . . . C12 C 0.1008(6) 0.8666(6) 0.7740(2) 0.0241(10) Uani 1 1 d . . . H12 H -0.0182 0.7708 0.7745 0.029 Uiso 1 1 calc R . . N1C N 1.2834(7) 1.0225(6) 0.5739(2) 0.0393(11) Uani 1 1 d . . . O3C O 1.3530(7) 1.1657(6) 0.5473(3) 0.0657(14) Uani 1 1 d . . . C3 C 0.6578(6) 0.5315(6) 0.6915(2) 0.0207(9) Uani 1 1 d . . . H5 H 0.6819 0.4330 0.6877 0.025 Uiso 1 1 calc R . . C11 C 0.1151(7) 1.0125(7) 0.7456(2) 0.0276(11) Uani 1 1 d . . . H11 H 0.0072 1.0172 0.7268 0.033 Uiso 1 1 calc R . . N4 N 1.0167(6) 0.5718(7) 0.5886(2) 0.0404(11) Uani 1 1 d . . . H4N H 1.0652 0.6855 0.5955 0.048 Uiso 1 1 calc R . . C21 C 0.7587(8) 0.3021(6) 0.5627(2) 0.0327(12) Uani 1 1 d . . . H21 H 0.6287 0.2351 0.5520 0.039 Uiso 1 1 calc R . . C17 C 0.2655(7) 0.2343(6) 0.9323(2) 0.0269(10) Uani 1 1 d . . . H17 H 0.1789 0.1243 0.9440 0.032 Uiso 1 1 calc R . . O2B O 0.0439(7) 0.7055(7) 0.9274(2) 0.0808(19) Uani 1 1 d . . . C19 C 0.7065(7) 0.5612(7) 0.5682(2) 0.0308(12) Uani 1 1 d . . . H19A H 0.5884 0.4795 0.5427 0.037 Uiso 1 1 calc R . . H19B H 0.7655 0.6637 0.5427 0.037 Uiso 1 1 calc R . . C24 C 1.1292(10) 0.4868(16) 0.5933(3) 0.082(3) Uani 1 1 d . . . H24 H 1.2594 0.5508 0.6043 0.098 Uiso 1 1 calc R . . C23 C 1.049(2) 0.309(2) 0.5817(5) 0.133(7) Uani 1 1 d . . . H23 H 1.1226 0.2482 0.5841 0.160 Uiso 1 1 calc R . . C22 C 0.869(2) 0.2239(12) 0.5672(4) 0.101(4) Uani 1 1 d . . . H22 H 0.8143 0.1010 0.5596 0.121 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 0.0120(3) 0.0146(3) 0.0244(3) 0.0047(2) 0.0027(2) 0.0051(2) N2 0.0137(18) 0.0195(19) 0.024(2) 0.0009(15) 0.0007(14) 0.0083(15) O2A 0.0201(19) 0.040(2) 0.060(3) 0.014(2) -0.0043(17) 0.0050(16) O1B 0.040(2) 0.085(3) 0.041(2) 0.031(2) 0.0179(18) 0.047(2) C4 0.014(2) 0.026(2) 0.025(2) 0.0047(19) 0.0047(17) 0.0109(18) N1 0.0197(18) 0.0142(18) 0.0181(18) 0.0071(14) 0.0033(14) 0.0112(15) O3A 0.0213(17) 0.0233(18) 0.035(2) -0.0013(15) -0.0059(14) 0.0005(14) N1B 0.023(2) 0.0172(19) 0.022(2) 0.0064(16) 0.0036(16) 0.0061(16) N3 0.0195(19) 0.0202(19) 0.0200(19) 0.0021(15) 0.0021(15) 0.0066(16) N1A 0.028(2) 0.022(2) 0.037(2) 0.0055(18) -0.0039(18) 0.0152(18) O3B 0.062(3) 0.041(2) 0.034(2) 0.0064(18) 0.0281(19) 0.023(2) C14 0.021(2) 0.018(2) 0.012(2) 0.0024(16) 0.0045(16) 0.0089(18) C6 0.033(3) 0.030(3) 0.029(3) 0.011(2) 0.011(2) 0.023(2) C1 0.0102(19) 0.018(2) 0.022(2) 0.0034(17) 0.0043(16) 0.0056(17) C8 0.017(2) 0.017(2) 0.020(2) 0.0004(17) 0.0031(16) 0.0106(17) C7 0.013(2) 0.011(2) 0.029(2) 0.0035(17) 0.0025(17) 0.0046(16) C16 0.040(3) 0.023(2) 0.018(2) 0.0047(19) 0.0044(19) 0.019(2) C18 0.027(2) 0.017(2) 0.023(2) 0.0060(18) 0.0044(19) 0.0034(19) O2C 0.047(3) 0.053(3) 0.073(3) 0.013(2) -0.002(2) 0.033(2) C2 0.020(2) 0.022(2) 0.023(2) 0.0119(18) 0.0084(17) 0.0109(18) C10 0.027(2) 0.026(3) 0.028(2) 0.009(2) 0.0034(19) 0.018(2) O1A 0.056(3) 0.042(2) 0.042(2) -0.0028(18) -0.0041(19) 0.036(2) C5 0.026(2) 0.033(3) 0.019(2) 0.0109(19) 0.0043(18) 0.020(2) C13 0.020(2) 0.016(2) 0.018(2) 0.0063(17) 0.0015(17) 0.0074(17) C9 0.023(2) 0.019(2) 0.026(2) 0.0058(18) 0.0044(18) 0.0117(19) O1C 0.044(3) 0.069(3) 0.059(3) 0.001(2) 0.004(2) 0.036(2) C15 0.026(2) 0.021(2) 0.017(2) 0.0044(18) 0.0019(17) 0.0125(19) C20 0.022(2) 0.032(3) 0.017(2) 0.0039(19) 0.0099(18) 0.013(2) C12 0.019(2) 0.023(2) 0.031(3) 0.000(2) -0.0026(19) 0.0117(19) N1C 0.042(3) 0.044(3) 0.040(3) -0.007(2) -0.004(2) 0.028(2) O3C 0.059(3) 0.042(3) 0.106(4) 0.013(3) -0.003(3) 0.031(2) C3 0.027(2) 0.023(2) 0.019(2) 0.0071(18) 0.0087(18) 0.0159(19) C11 0.021(2) 0.033(3) 0.035(3) 0.007(2) -0.001(2) 0.017(2) N4 0.038(3) 0.045(3) 0.027(2) 0.006(2) 0.0051(19) 0.009(2) C21 0.047(3) 0.018(2) 0.019(2) 0.0038(19) 0.008(2) 0.001(2) C17 0.035(3) 0.021(2) 0.022(2) 0.0090(19) 0.006(2) 0.008(2) O2B 0.055(3) 0.067(3) 0.053(3) 0.018(3) -0.026(2) -0.032(2) C19 0.034(3) 0.052(3) 0.019(2) 0.008(2) 0.009(2) 0.030(3) C24 0.038(4) 0.216(11) 0.025(3) 0.034(5) 0.016(3) 0.082(6) C23 0.271(18) 0.241(17) 0.048(5) 0.068(8) 0.078(9) 0.246(17) C22 0.248(14) 0.061(5) 0.043(5) 0.032(4) 0.068(7) 0.105(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 N2 1.948(4) . ? Cu1 N3 1.958(4) . ? Cu1 O1A 2.126(4) . ? Cu1 N1 2.180(4) . ? Cu1 O1B 2.355(5) . ? N2 C8 1.338(6) . ? N2 C12 1.357(6) . ? O2A N1A 1.251(6) . ? O1B N1B 1.231(5) . ? C4 C3 1.386(6) . ? C4 C5 1.374(6) . ? C4 C19 1.514(6) . ? N1 C1 1.440(5) . ? N1 C13 1.490(5) . ? N1 C7 1.494(5) . ? O3A N1A 1.228(5) . ? N1B O2B 1.220(6) . ? N1B O3B 1.226(5) . ? N3 C14 1.348(6) . ? N3 C18 1.341(6) . ? N1A O1A 1.268(6) . ? C14 C15 1.390(6) . ? C14 C13 1.515(6) . ? C6 C5 1.392(6) . ? C6 C1 1.402(6) . ? C1 C2 1.381(6) . ? C8 C9 1.386(6) . ? C8 C7 1.501(6) . ? C16 C17 1.390(7) . ? C16 C15 1.390(6) . ? C18 C17 1.372(7) . ? O2C N1C 1.240(6) . ? C2 C3 1.384(6) . ? C10 C11 1.374(7) . ? C10 C9 1.392(6) . ? O1C N1C 1.257(6) . ? C20 C21 1.346(7) . ? C20 N4 1.353(6) . ? C20 C19 1.489(6) . ? C12 C11 1.379(7) . ? N1C O3C 1.276(7) . ? N4 C24 1.397(10) . ? C21 C22 1.331(12) . ? C24 C23 1.377(16) . ? C23 C22 1.308(18) . ? 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 N2 Cu1 N3 164.85(16) . . ? N2 Cu1 O1A 98.25(15) . . ? N3 Cu1 O1A 96.12(16) . . ? N2 Cu1 N1 82.06(14) . . ? N3 Cu1 N1 83.22(14) . . ? O1A Cu1 N1 147.73(15) . . ? N2 Cu1 O1B 87.57(15) . . ? N3 Cu1 O1B 88.28(14) . . ? O1A Cu1 O1B 124.39(15) . . ? N1 Cu1 O1B 87.87(14) . . ? C8 N2 C12 119.6(4) . . ? C8 N2 Cu1 114.6(3) . . ? C12 N2 Cu1 125.8(3) . . ? N1B O1B Cu1 100.6(3) . . ? C3 C4 C5 117.5(4) . . ? C3 C4 C19 122.0(4) . . ? C5 C4 C19 120.4(4) . . ? C1 N1 C13 113.8(3) . . ? C1 N1 C7 113.6(3) . . ? C13 N1 C7 112.8(3) . . ? C1 N1 Cu1 113.8(3) . . ? C13 N1 Cu1 101.2(2) . . ? C7 N1 Cu1 100.4(2) . . ? O2B N1B O3B 123.8(5) . . ? O2B N1B O1B 117.1(5) . . ? O3B N1B O1B 119.1(4) . . ? C14 N3 C18 119.5(4) . . ? C14 N3 Cu1 114.6(3) . . ? C18 N3 Cu1 125.8(3) . . ? O3A N1A O2A 121.9(4) . . ? O3A N1A O1A 121.2(4) . . ? O2A N1A O1A 117.0(4) . . ? N3 C14 C15 121.3(4) . . ? N3 C14 C13 116.1(4) . . ? C15 C14 C13 122.6(4) . . ? C5 C6 C1 120.2(4) . . ? C2 C1 C6 117.8(4) . . ? C2 C1 N1 120.8(4) . . ? C6 C1 N1 121.4(4) . . ? N2 C8 C9 121.0(4) . . ? N2 C8 C7 116.7(4) . . ? C9 C8 C7 122.3(4) . . ? N1 C7 C8 110.4(3) . . ? C17 C16 C15 119.0(4) . . ? N3 C18 C17 122.2(5) . . ? C3 C2 C1 121.1(4) . . ? C11 C10 C9 119.0(4) . . ? N1A O1A Cu1 102.3(3) . . ? C4 C5 C6 121.8(4) . . ? N1 C13 C14 110.9(3) . . ? C8 C9 C10 119.5(4) . . ? C14 C15 C16 119.0(4) . . ? C21 C20 N4 120.2(5) . . ? C21 C20 C19 119.2(5) . . ? N4 C20 C19 120.5(5) . . ? N2 C12 C11 121.6(4) . . ? O2C N1C O1C 121.3(5) . . ? O2C N1C O3C 119.5(5) . . ? O1C N1C O3C 119.1(5) . . ? C2 C3 C4 121.6(4) . . ? C12 C11 C10 119.3(4) . . ? C20 N4 C24 118.8(6) . . ? C20 C21 C22 119.9(7) . . ? C18 C17 C16 119.1(4) . . ? C20 C19 C4 113.3(4) . . ? C23 C24 N4 119.0(8) . . ? C22 C23 C24 119.1(7) . . ? C23 C22 C21 123.0(9) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.13 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.774 _refine_diff_density_min -0.790 _refine_diff_density_rms 0.089 # Attachment 'structure__6_.cif' data_c:\gaelle~1\articl~2\struct~2\(6)-co~1\annsad3 _database_code_depnum_ccdc_archive 'CCDC 649301' _audit_creation_method SHELXL-97 _chemical_name_systematic ; none ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety 'C26 H30 Co N4 O6 S' _chemical_formula_sum 'C26 H30 Co N4 O6 S' _chemical_formula_weight 585.53 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Co Co 0.3494 0.9721 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.6604(2) _cell_length_b 10.7821(2) _cell_length_c 11.5302(2) _cell_angle_alpha 80.9020(10) _cell_angle_beta 84.2830(10) _cell_angle_gamma 79.0480(10) _cell_volume 1281.48(4) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 27.7 _exptl_crystal_description plates _exptl_crystal_colour purple _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.517 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 610 _exptl_absorpt_coefficient_mu 0.801 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 24896 _diffrn_reflns_av_R_equivalents 0.0667 _diffrn_reflns_av_sigmaI/netI 0.0696 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 27.73 _reflns_number_total 5946 _reflns_number_gt 4289 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0566P)^2^+0.0696P] 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 5946 _refine_ls_number_parameters 350 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1050 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Co1 Co 0.19040(3) 0.36181(3) 0.43883(3) 0.01226(11) Uani 1 1 d . . . S1A S -0.04080(6) 0.34312(5) 0.64503(5) 0.01391(14) Uani 1 1 d . . . O1B O 0.27508(17) 0.48814(17) 0.52109(15) 0.0200(4) Uani 1 1 d . . . N2 N 0.09965(18) 0.23753(18) 0.36317(16) 0.0139(4) Uani 1 1 d . . . O1A O 0.09394(15) 0.31709(16) 0.59797(14) 0.0188(4) Uani 1 1 d . . . O4A O -0.12354(16) 0.30428(15) 0.56746(16) 0.0218(4) Uani 1 1 d . . . O2A O -0.07795(16) 0.48196(15) 0.64968(14) 0.0182(4) Uani 1 1 d . . . N3 N 0.34756(18) 0.37094(18) 0.30988(17) 0.0145(4) Uani 1 1 d . . . O3A O -0.05131(18) 0.27265(17) 0.76381(15) 0.0258(4) Uani 1 1 d . . . N1 N 0.31780(18) 0.16580(17) 0.47947(16) 0.0121(4) Uani 1 1 d . . . N4 N 0.6676(2) -0.08149(19) 0.88931(18) 0.0206(5) Uani 1 1 d . . . C8 C 0.1307(2) 0.1127(2) 0.4044(2) 0.0148(5) Uani 1 1 d . . . C3 C 0.4306(2) 0.1180(2) 0.7844(2) 0.0190(5) Uani 1 1 d . . . H3 H 0.4012 0.0888 0.8627 0.023 Uiso 1 1 calc R . . C6 C 0.5122(2) 0.2027(2) 0.5575(2) 0.0171(5) Uani 1 1 d . . . H6 H 0.5409 0.2332 0.4794 0.021 Uiso 1 1 calc R . . C4 C 0.5494(2) 0.1557(2) 0.7649(2) 0.0175(5) Uani 1 1 d . . . C10 C -0.0064(2) 0.0591(2) 0.2762(2) 0.0218(6) Uani 1 1 d . . . H10 H -0.0417 -0.0022 0.2453 0.026 Uiso 1 1 calc R . . C12 C 0.0148(2) 0.2735(2) 0.2808(2) 0.0186(5) Uani 1 1 d . . . H12 H -0.0080 0.3618 0.2522 0.022 Uiso 1 1 calc R . . C20 C 0.7031(2) 0.0232(2) 0.9148(2) 0.0176(5) Uani 1 1 d . . . C7 C 0.2211(2) 0.0804(2) 0.5017(2) 0.0152(5) Uani 1 1 d . . . H7A H 0.1724 0.0910 0.5783 0.018 Uiso 1 1 calc R . . H7B H 0.2646 -0.0097 0.5053 0.018 Uiso 1 1 calc R . . C18 C 0.3716(2) 0.4798(2) 0.2436(2) 0.0181(5) Uani 1 1 d . . . H18 H 0.3163 0.5578 0.2551 0.022 Uiso 1 1 calc R . . C21 C 0.8016(2) 0.0160(2) 0.9889(2) 0.0208(6) Uani 1 1 d . . . H21 H 0.8255 0.0918 1.0049 0.025 Uiso 1 1 calc R . . C5 C 0.5884(2) 0.1999(2) 0.6490(2) 0.0191(5) Uani 1 1 d . . . H5 H 0.6682 0.2284 0.6326 0.023 Uiso 1 1 calc R . . C1 C 0.3948(2) 0.1620(2) 0.5774(2) 0.0136(5) Uani 1 1 d . . . C11 C -0.0412(2) 0.1876(2) 0.2357(2) 0.0218(6) Uani 1 1 d . . . H11 H -0.1021 0.2161 0.1781 0.026 Uiso 1 1 calc R . . C23 C 0.8264(2) -0.2106(2) 1.0138(2) 0.0235(6) Uani 1 1 d . . . H23 H 0.8660 -0.2931 1.0475 0.028 Uiso 1 1 calc R . . C14 C 0.4275(2) 0.2618(2) 0.29453(19) 0.0142(5) Uani 1 1 d . . . C17 C 0.4728(2) 0.4824(2) 0.1603(2) 0.0217(6) Uani 1 1 d . . . H17 H 0.4871 0.5608 0.1152 0.026 Uiso 1 1 calc R . . C2 C 0.3537(2) 0.1217(2) 0.6936(2) 0.0178(5) Uani 1 1 d . . . H2 H 0.2723 0.0966 0.7105 0.021 Uiso 1 1 calc R . . C13 C 0.3967(2) 0.1424(2) 0.3686(2) 0.0151(5) Uani 1 1 d . . . H13A H 0.3503 0.0987 0.3217 0.018 Uiso 1 1 calc R . . H13B H 0.4778 0.0844 0.3885 0.018 Uiso 1 1 calc R . . C9 C 0.0807(2) 0.0202(2) 0.3625(2) 0.0188(5) Uani 1 1 d . . . H9 H 0.1053 -0.0676 0.3920 0.023 Uiso 1 1 calc R . . C24 C 0.7296(3) -0.1951(2) 0.9384(2) 0.0244(6) Uani 1 1 d . . . H24 H 0.7054 -0.2698 0.9202 0.029 Uiso 1 1 calc R . . C22 C 0.8637(2) -0.1020(2) 1.0385(2) 0.0225(6) Uani 1 1 d . . . H22 H 0.9308 -0.1085 1.0886 0.027 Uiso 1 1 calc R . . C16 C 0.5541(2) 0.3688(2) 0.1428(2) 0.0213(6) Uani 1 1 d . . . H16 H 0.6241 0.3679 0.0849 0.026 Uiso 1 1 calc R . . C15 C 0.5308(2) 0.2570(2) 0.2116(2) 0.0192(5) Uani 1 1 d . . . H15 H 0.5851 0.1779 0.2021 0.023 Uiso 1 1 calc R . . C19 C 0.6314(3) 0.1525(2) 0.8652(2) 0.0235(6) Uani 1 1 d . . . H19A H 0.5758 0.1890 0.9300 0.028 Uiso 1 1 calc R . . H19B H 0.6947 0.2091 0.8380 0.028 Uiso 1 1 calc R . . O1C O -0.18070(18) 0.33438(16) 0.96595(16) 0.0247(4) Uani 1 1 d . . . H1C H -0.1428 0.3136 0.9026 0.030 Uiso 1 1 calc R . . C1C C -0.1534(3) 0.4526(3) 0.9830(3) 0.0302(7) Uani 1 1 d . . . H2C2 H -0.2277 0.5001 1.0239 0.045 Uiso 1 1 calc R . . H2C3 H -0.1341 0.5019 0.9064 0.045 Uiso 1 1 calc R . . H2C1 H -0.0793 0.4383 1.0304 0.045 Uiso 1 1 calc R . . C1B C 0.2921(3) 0.4804(3) 0.6430(2) 0.0335(7) Uani 1 1 d . . . H2B2 H 0.2126 0.4659 0.6892 0.050 Uiso 1 1 calc R . . H2B3 H 0.3140 0.5604 0.6580 0.050 Uiso 1 1 calc R . . H2B1 H 0.3615 0.4095 0.6658 0.050 Uiso 1 1 calc R . . H1B H 0.233(3) 0.560(3) 0.502(3) 0.045(10) Uiso 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 Co1 0.01367(18) 0.01187(17) 0.01062(17) -0.00331(12) -0.00077(12) 0.00062(12) S1A 0.0157(3) 0.0116(3) 0.0127(3) -0.0012(2) 0.0011(2) 0.0006(2) O1B 0.0227(10) 0.0180(9) 0.0205(10) -0.0073(8) -0.0062(8) -0.0003(8) N2 0.0150(10) 0.0163(10) 0.0109(10) -0.0042(8) -0.0001(8) -0.0020(8) O1A 0.0154(9) 0.0252(9) 0.0129(8) -0.0032(7) 0.0019(7) 0.0031(7) O4A 0.0234(10) 0.0144(9) 0.0297(10) -0.0045(8) -0.0062(8) -0.0053(7) O2A 0.0218(9) 0.0125(8) 0.0191(9) -0.0040(7) -0.0060(7) 0.0036(7) N3 0.0146(10) 0.0139(10) 0.0143(10) -0.0021(8) -0.0021(8) 0.0002(8) O3A 0.0328(11) 0.0243(10) 0.0142(9) 0.0041(7) 0.0056(8) 0.0004(8) N1 0.0141(10) 0.0124(10) 0.0095(9) -0.0024(8) 0.0010(8) -0.0016(8) N4 0.0251(12) 0.0188(11) 0.0184(11) -0.0050(9) -0.0068(9) -0.0005(9) C8 0.0156(13) 0.0177(12) 0.0113(11) -0.0054(10) 0.0031(9) -0.0027(10) C3 0.0245(14) 0.0190(13) 0.0118(12) -0.0019(10) -0.0019(10) 0.0002(10) C6 0.0211(13) 0.0152(12) 0.0135(12) -0.0004(10) 0.0002(10) -0.0018(10) C4 0.0216(14) 0.0114(11) 0.0194(13) -0.0013(10) -0.0078(10) -0.0002(10) C10 0.0253(14) 0.0284(14) 0.0168(13) -0.0099(11) 0.0011(11) -0.0132(11) C12 0.0199(13) 0.0199(13) 0.0152(12) -0.0017(10) -0.0017(10) -0.0021(10) C20 0.0187(13) 0.0212(13) 0.0120(12) -0.0035(10) 0.0001(10) -0.0015(10) C7 0.0186(13) 0.0119(11) 0.0144(12) -0.0010(9) -0.0009(10) -0.0020(9) C18 0.0210(13) 0.0164(12) 0.0159(12) 0.0001(10) -0.0022(10) -0.0020(10) C21 0.0233(14) 0.0224(13) 0.0186(13) -0.0057(11) -0.0028(11) -0.0057(11) C5 0.0195(13) 0.0157(12) 0.0223(13) -0.0028(10) -0.0034(10) -0.0027(10) C1 0.0152(12) 0.0096(11) 0.0145(12) -0.0025(9) -0.0044(9) 0.0039(9) C11 0.0250(14) 0.0296(14) 0.0125(12) -0.0031(11) -0.0048(10) -0.0077(11) C23 0.0252(15) 0.0213(13) 0.0215(14) -0.0058(11) -0.0047(11) 0.0058(11) C14 0.0141(12) 0.0189(12) 0.0105(11) -0.0039(9) -0.0019(9) -0.0032(9) C17 0.0257(15) 0.0220(13) 0.0166(13) 0.0022(11) -0.0042(11) -0.0051(11) C2 0.0161(13) 0.0192(12) 0.0173(13) -0.0031(10) 0.0004(10) -0.0019(10) C13 0.0166(13) 0.0135(11) 0.0146(12) -0.0046(9) 0.0001(10) 0.0003(9) C9 0.0222(14) 0.0193(13) 0.0154(12) -0.0051(10) 0.0029(10) -0.0056(10) C24 0.0309(16) 0.0189(13) 0.0243(14) -0.0060(11) -0.0080(12) -0.0009(11) C22 0.0192(14) 0.0313(15) 0.0170(13) -0.0066(11) -0.0036(10) -0.0006(11) C16 0.0198(14) 0.0297(14) 0.0146(12) -0.0020(11) 0.0001(10) -0.0069(11) C15 0.0207(14) 0.0212(13) 0.0152(12) -0.0048(10) -0.0007(10) -0.0009(10) C19 0.0312(16) 0.0185(13) 0.0231(14) -0.0039(11) -0.0108(12) -0.0047(11) O1C 0.0291(11) 0.0242(10) 0.0216(10) -0.0056(8) 0.0053(8) -0.0083(8) C1C 0.0329(17) 0.0288(15) 0.0317(16) -0.0061(13) -0.0004(13) -0.0117(13) C1B 0.0457(19) 0.0297(15) 0.0271(15) -0.0140(12) -0.0207(14) 0.0063(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 Co1 O1A 2.0468(16) . ? Co1 O2A 2.0613(15) 2_566 ? Co1 N2 2.1268(19) . ? Co1 N3 2.133(2) . ? Co1 O1B 2.1486(17) . ? Co1 N1 2.2921(19) . ? S1A O3A 1.4623(17) . ? S1A O4A 1.4728(17) . ? S1A O1A 1.4752(17) . ? S1A O2A 1.4821(16) . ? O1B C1B 1.422(3) . ? N2 C12 1.339(3) . ? N2 C8 1.344(3) . ? O2A Co1 2.0613(15) 2_566 ? N3 C14 1.340(3) . ? N3 C18 1.349(3) . ? N1 C1 1.452(3) . ? N1 C7 1.487(3) . ? N1 C13 1.488(3) . ? N4 C20 1.339(3) . ? N4 C24 1.344(3) . ? C8 C9 1.385(3) . ? C8 C7 1.508(3) . ? C3 C2 1.384(3) . ? C3 C4 1.389(3) . ? C6 C5 1.389(3) . ? C6 C1 1.389(3) . ? C4 C5 1.395(3) . ? C4 C19 1.511(3) . ? C10 C11 1.382(4) . ? C10 C9 1.390(3) . ? C12 C11 1.382(3) . ? C20 C21 1.402(3) . ? C20 C19 1.512(3) . ? C18 C17 1.373(4) . ? C21 C22 1.382(4) . ? C1 C2 1.395(3) . ? C23 C22 1.383(4) . ? C23 C24 1.384(3) . ? C14 C15 1.383(3) . ? C14 C13 1.501(3) . ? C17 C16 1.390(4) . ? C16 C15 1.385(3) . ? O1C C1C 1.407(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 O1A Co1 O2A 106.80(7) . 2_566 ? O1A Co1 N2 90.25(7) . . ? O2A Co1 N2 90.33(7) 2_566 . ? O1A Co1 N3 158.85(7) . . ? O2A Co1 N3 92.81(7) 2_566 . ? N2 Co1 N3 97.61(7) . . ? O1A Co1 O1B 87.43(7) . . ? O2A Co1 O1B 89.34(7) 2_566 . ? N2 Co1 O1B 177.46(7) . . ? N3 Co1 O1B 84.92(7) . . ? O1A Co1 N1 86.06(6) . . ? O2A Co1 N1 161.42(7) 2_566 . ? N2 Co1 N1 75.98(7) . . ? N3 Co1 N1 76.94(7) . . ? O1B Co1 N1 104.88(7) . . ? O3A S1A O4A 110.81(10) . . ? O3A S1A O1A 108.54(10) . . ? O4A S1A O1A 109.80(10) . . ? O3A S1A O2A 109.72(10) . . ? O4A S1A O2A 109.53(9) . . ? O1A S1A O2A 108.40(10) . . ? C1B O1B Co1 127.23(16) . . ? C12 N2 C8 118.6(2) . . ? C12 N2 Co1 125.68(16) . . ? C8 N2 Co1 115.74(15) . . ? S1A O1A Co1 135.03(10) . . ? S1A O2A Co1 138.29(10) . 2_566 ? C14 N3 C18 118.2(2) . . ? C14 N3 Co1 117.83(15) . . ? C18 N3 Co1 123.93(16) . . ? C1 N1 C7 115.08(17) . . ? C1 N1 C13 112.76(18) . . ? C7 N1 C13 109.33(17) . . ? C1 N1 Co1 111.16(13) . . ? C7 N1 Co1 101.43(13) . . ? C13 N1 Co1 106.15(13) . . ? C20 N4 C24 117.3(2) . . ? N2 C8 C9 122.3(2) . . ? N2 C8 C7 115.4(2) . . ? C9 C8 C7 122.2(2) . . ? C2 C3 C4 122.1(2) . . ? C5 C6 C1 121.5(2) . . ? C3 C4 C5 117.3(2) . . ? C3 C4 C19 121.4(2) . . ? C5 C4 C19 121.3(2) . . ? C11 C10 C9 119.6(2) . . ? N2 C12 C11 122.7(2) . . ? N4 C20 C21 121.9(2) . . ? N4 C20 C19 118.7(2) . . ? C21 C20 C19 119.4(2) . . ? N1 C7 C8 109.62(18) . . ? N3 C18 C17 122.6(2) . . ? C22 C21 C20 119.6(2) . . ? C6 C5 C4 120.9(2) . . ? C6 C1 C2 117.7(2) . . ? C6 C1 N1 120.0(2) . . ? C2 C1 N1 122.2(2) . . ? C12 C11 C10 118.4(2) . . ? C22 C23 C24 117.9(2) . . ? N3 C14 C15 122.4(2) . . ? N3 C14 C13 116.7(2) . . ? C15 C14 C13 120.8(2) . . ? C18 C17 C16 119.2(2) . . ? C3 C2 C1 120.4(2) . . ? N1 C13 C14 113.58(19) . . ? C8 C9 C10 118.4(2) . . ? N4 C24 C23 124.4(2) . . ? C21 C22 C23 118.9(2) . . ? C15 C16 C17 118.5(2) . . ? C16 C15 C14 119.1(2) . . ? C4 C19 C20 116.6(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.73 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.821 _refine_diff_density_min -0.645 _refine_diff_density_rms 0.088 # Attachment 'structure__7_.cif' data_c:\gaelle~1\articl~2\struct~2\(7)-cu~1\gr4 _database_code_depnum_ccdc_archive 'CCDC 649302' _audit_creation_method SHELXL-97 _chemical_name_systematic ; none ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety 'C24 H29 Cu N4 O8.25 S1.25' _chemical_formula_sum 'C24 H29 Cu N4 O8.25 S1.25' _chemical_formula_weight 609.13 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' S S 0.1246 0.1234 '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 9.4677(2) _cell_length_b 10.1790(2) _cell_length_c 16.2431(4) _cell_angle_alpha 79.7890(10) _cell_angle_beta 75.9070(10) _cell_angle_gamma 71.3780(10) _cell_volume 1430.32(5) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_theta_max 32.7 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.907 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 22892 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 32.68 _reflns_number_total 10429 _reflns_number_gt 9144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0955P)^2^+0.9129P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10429 _refine_ls_number_parameters 414 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1542 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.069 _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 0.03390(2) 0.07364(2) 0.073802(13) 0.01481(7) Uani 1 1 d . . . N1 N 0.21514(17) 0.08741(15) 0.11387(9) 0.0149(2) Uani 1 1 d . . . C14 C 0.1962(2) 0.26190(18) -0.01025(11) 0.0179(3) Uani 1 1 d . . . N3 N 0.05730(18) 0.24548(16) -0.00068(10) 0.0176(3) Uani 1 1 d . . . N2 N 0.05019(18) -0.08950(16) 0.16334(10) 0.0177(3) Uani 1 1 d . . . C1 C 0.1656(2) 0.16858(17) 0.18747(11) 0.0159(3) Uani 1 1 d . . . C8 C 0.1896(2) -0.13967(18) 0.18207(11) 0.0180(3) Uani 1 1 d . . . C7 C 0.3003(2) -0.05994(18) 0.13761(12) 0.0187(3) Uani 1 1 d . . . H7A H 0.3686 -0.0626 0.1758 0.022 Uiso 1 1 calc R . . H7B H 0.3635 -0.1030 0.0857 0.022 Uiso 1 1 calc R . . C18 C -0.0441(2) 0.33724(19) -0.04431(12) 0.0217(3) Uani 1 1 d . . . H18 H -0.1424 0.3262 -0.0370 0.026 Uiso 1 1 calc R . . C2 C 0.0118(2) 0.21504(19) 0.22400(12) 0.0198(3) Uani 1 1 d . . . H2 H -0.0620 0.1987 0.1997 0.024 Uiso 1 1 calc R . . C13 C 0.3033(2) 0.15296(19) 0.03814(11) 0.0182(3) Uani 1 1 d . . . H13B H 0.3697 0.0809 0.0007 0.022 Uiso 1 1 calc R . . H13A H 0.3687 0.1959 0.0570 0.022 Uiso 1 1 calc R . . C3 C -0.0337(2) 0.2859(2) 0.29653(12) 0.0235(4) Uani 1 1 d . . . H3 H -0.1389 0.3183 0.3209 0.028 Uiso 1 1 calc R . . C12 C -0.0560(2) -0.1551(2) 0.20120(12) 0.0222(3) Uani 1 1 d . . . H12 H -0.1551 -0.1185 0.1887 0.027 Uiso 1 1 calc R . . C9 C 0.2298(3) -0.2602(2) 0.23693(13) 0.0247(4) Uani 1 1 d . . . H9 H 0.3298 -0.2951 0.2483 0.030 Uiso 1 1 calc R . . C11 C -0.0245(3) -0.2745(2) 0.25779(14) 0.0279(4) Uani 1 1 d . . . H11 H -0.1013 -0.3184 0.2845 0.033 Uiso 1 1 calc R . . C4 C 0.0719(3) 0.3097(2) 0.33347(12) 0.0244(4) Uani 1 1 d . . . C17 C -0.0075(3) 0.4476(2) -0.09974(13) 0.0253(4) Uani 1 1 d . . . H17 H -0.0804 0.5118 -0.1297 0.030 Uiso 1 1 calc R . . C15 C 0.2399(2) 0.3696(2) -0.06539(13) 0.0235(4) Uani 1 1 d . . . H15 H 0.3388 0.3791 -0.0718 0.028 Uiso 1 1 calc R . . C6 C 0.2725(2) 0.1965(2) 0.22201(13) 0.0234(3) Uani 1 1 d . . . H6 H 0.3773 0.1683 0.1961 0.028 Uiso 1 1 calc R . . C10 C 0.1207(3) -0.3289(2) 0.27501(14) 0.0292(4) Uani 1 1 d . . . H10 H 0.1455 -0.4122 0.3124 0.035 Uiso 1 1 calc R . . C16 C 0.1358(3) 0.4630(2) -0.11082(13) 0.0276(4) Uani 1 1 d . . . H16 H 0.1630 0.5369 -0.1493 0.033 Uiso 1 1 calc R . . C5 C 0.2247(3) 0.2661(2) 0.29462(14) 0.0283(4) Uani 1 1 d . . . H5 H 0.2980 0.2843 0.3183 0.034 Uiso 1 1 calc R . . C19 C 0.0223(4) 0.3736(2) 0.41726(14) 0.0352(5) Uani 1 1 d . . . H19B H 0.1069 0.4004 0.4287 0.042 Uiso 1 1 calc R . . H19A H -0.0648 0.4584 0.4140 0.042 Uiso 1 1 calc R . . C20 C -0.0231(4) 0.2683(2) 0.48837(14) 0.0365(6) Uani 1 1 d . . . N4 N -0.1682(4) 0.2683(3) 0.51001(15) 0.0508(7) Uani 1 1 d . . . H4N H -0.2371 0.3342 0.4863 0.075 Uiso 0.50 1 calc PR . . C21 C 0.0833(4) 0.1685(3) 0.52697(17) 0.0463(7) Uani 1 1 d . . . H21 H 0.1864 0.1697 0.5130 0.056 Uiso 1 1 calc R . . C24 C -0.2110(5) 0.1674(4) 0.56850(19) 0.0569(9) Uani 1 1 d . . . H24 H -0.3147 0.1683 0.5830 0.068 Uiso 1 1 calc R . . C23 C -0.1065(6) 0.0652(3) 0.60639(17) 0.0583(11) Uani 1 1 d . . . H23 H -0.1364 -0.0060 0.6465 0.070 Uiso 1 1 calc R . . C22 C 0.0407(5) 0.0663(3) 0.58624(19) 0.0565(10) Uani 1 1 d . . . H22 H 0.1145 -0.0035 0.6130 0.068 Uiso 1 1 calc R . . O1A O -0.14564(14) 0.06675(14) 0.03727(9) 0.0191(2) Uani 1 1 d . . . O3A O -0.27642(19) 0.2021(2) 0.15447(12) 0.0348(4) Uani 1 1 d . . . O2A O -0.38241(18) 0.24468(17) 0.02693(11) 0.0288(3) Uani 1 1 d . . . O4A O -0.38179(17) 0.03431(18) 0.12102(11) 0.0279(3) Uani 1 1 d . . . O1 O 0.5399(4) -0.1010(4) 0.2853(2) 0.0609(10) Uani 0.72 1 d P . . O2 O 0.5385(4) -0.5533(3) 0.2240(3) 0.0621(9) Uani 0.76 1 d P . . O5 O -0.4032(5) 0.5012(4) -0.0816(4) 0.0572(12) Uani 0.55 1 d P . . O4B O -0.6481(9) 0.4853(11) 0.5319(4) 0.051(3) Uani 0.25 1 d PD . . O3B O -0.6111(10) 0.4618(10) 0.3853(5) 0.058(3) Uani 0.25 1 d PD . . O1B O -0.3989(8) 0.4574(13) 0.4519(8) 0.083(5) Uani 0.25 1 d PD . . O2B O -0.5191(19) 0.2663(10) 0.4722(11) 0.112(6) Uani 0.25 1 d PD . . S1A S -0.30257(5) 0.13987(5) 0.08653(3) 0.02002(10) Uani 1 1 d . . . S1B S -0.5515(4) 0.4151(3) 0.4565(2) 0.0456(6) Uani 0.25 1 d P . . O3 O 0.3567(13) -0.0951(11) 0.6718(7) 0.059(3) Uani 0.24 1 d P . . O6 O -0.4521(19) 0.029(3) 0.4214(7) 0.123(8) Uani 0.23 1 d P . . O4 O -0.3476(4) -0.3843(4) 0.3031(2) 0.0580(8) Uani 0.76 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 0.01274(11) 0.01517(10) 0.01629(11) -0.00073(7) -0.00273(7) -0.00437(7) N1 0.0135(6) 0.0151(6) 0.0143(6) -0.0012(5) -0.0003(5) -0.0040(5) C14 0.0207(8) 0.0173(7) 0.0155(7) -0.0023(5) -0.0014(6) -0.0065(6) N3 0.0186(7) 0.0154(6) 0.0184(6) -0.0012(5) -0.0041(5) -0.0045(5) N2 0.0186(7) 0.0169(6) 0.0174(6) -0.0008(5) -0.0018(5) -0.0069(5) C1 0.0167(7) 0.0159(6) 0.0139(6) -0.0003(5) -0.0008(5) -0.0055(5) C8 0.0200(8) 0.0152(7) 0.0174(7) -0.0020(5) -0.0025(6) -0.0038(6) C7 0.0145(7) 0.0165(7) 0.0230(8) -0.0002(6) -0.0045(6) -0.0021(6) C18 0.0255(9) 0.0162(7) 0.0221(8) -0.0023(6) -0.0089(7) -0.0012(6) C2 0.0177(8) 0.0209(8) 0.0173(7) -0.0008(6) -0.0012(6) -0.0031(6) C13 0.0147(7) 0.0227(8) 0.0157(7) -0.0003(6) 0.0002(5) -0.0065(6) C3 0.0246(9) 0.0216(8) 0.0177(8) -0.0024(6) 0.0032(6) -0.0030(7) C12 0.0239(9) 0.0231(8) 0.0208(8) -0.0017(6) 0.0000(7) -0.0118(7) C9 0.0295(10) 0.0173(7) 0.0256(9) 0.0014(6) -0.0078(7) -0.0048(7) C11 0.0386(11) 0.0242(9) 0.0235(9) -0.0002(7) -0.0014(8) -0.0177(8) C4 0.0357(10) 0.0186(8) 0.0168(8) -0.0021(6) 0.0005(7) -0.0088(7) C17 0.0363(11) 0.0168(7) 0.0210(8) -0.0001(6) -0.0098(7) -0.0032(7) C15 0.0280(9) 0.0214(8) 0.0199(8) 0.0009(6) -0.0009(7) -0.0103(7) C6 0.0202(8) 0.0298(9) 0.0227(8) -0.0097(7) -0.0004(6) -0.0100(7) C10 0.0437(12) 0.0188(8) 0.0253(9) 0.0030(7) -0.0077(9) -0.0117(8) C16 0.0400(12) 0.0199(8) 0.0213(8) 0.0035(7) -0.0051(8) -0.0103(8) C5 0.0315(10) 0.0330(10) 0.0255(9) -0.0101(8) -0.0039(8) -0.0138(8) C19 0.0584(16) 0.0242(9) 0.0197(9) -0.0063(7) 0.0041(9) -0.0141(10) C20 0.0632(17) 0.0235(9) 0.0156(8) -0.0051(7) 0.0025(9) -0.0089(10) N4 0.0664(18) 0.0447(13) 0.0260(10) -0.0021(9) 0.0068(11) -0.0078(12) C21 0.068(2) 0.0397(14) 0.0262(11) -0.0106(10) -0.0067(12) -0.0066(13) C24 0.081(3) 0.0549(18) 0.0270(12) -0.0052(12) 0.0084(14) -0.0236(18) C23 0.115(3) 0.0345(13) 0.0201(11) -0.0027(9) -0.0018(15) -0.0238(17) C22 0.100(3) 0.0338(14) 0.0265(12) -0.0066(10) -0.0138(15) -0.0038(16) O1A 0.0104(5) 0.0226(6) 0.0231(6) -0.0079(5) -0.0008(4) -0.0023(4) O3A 0.0188(7) 0.0477(10) 0.0398(9) -0.0282(8) -0.0050(6) -0.0006(6) O2A 0.0191(7) 0.0266(7) 0.0374(8) -0.0039(6) -0.0087(6) 0.0005(5) O4A 0.0164(6) 0.0356(8) 0.0298(7) -0.0035(6) 0.0023(5) -0.0100(6) O1 0.0396(16) 0.081(2) 0.0514(18) 0.0301(17) -0.0085(13) -0.0233(16) O2 0.0505(18) 0.0416(16) 0.087(3) -0.0282(16) -0.0026(17) 0.0002(13) O5 0.043(2) 0.0269(16) 0.089(3) -0.0069(19) -0.008(2) 0.0031(15) O4B 0.032(4) 0.084(7) 0.013(3) 0.006(3) 0.001(3) 0.007(4) O3B 0.043(5) 0.082(7) 0.060(6) -0.049(5) -0.021(4) -0.004(4) O1B 0.019(4) 0.113(11) 0.079(8) 0.064(8) -0.014(4) -0.005(5) O2B 0.133(15) 0.045(6) 0.155(16) 0.027(8) -0.040(12) -0.034(8) S1A 0.01086(17) 0.0244(2) 0.0240(2) -0.00883(16) -0.00177(14) -0.00207(15) S1B 0.0376(14) 0.0487(15) 0.0447(15) 0.0030(12) -0.0080(11) -0.0092(12) O3 0.058(6) 0.051(5) 0.051(5) -0.004(4) -0.017(5) 0.013(5) O6 0.078(10) 0.25(2) 0.016(4) -0.023(8) -0.012(5) -0.009(12) O4 0.060(2) 0.0580(19) 0.0524(18) -0.0097(15) -0.0001(15) -0.0191(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1A 1.9566(13) . ? Cu1 N3 1.9846(15) . ? Cu1 N2 1.9965(15) . ? Cu1 N1 2.0292(15) . ? Cu1 O1A 2.3314(13) 2 ? N1 C1 1.470(2) . ? N1 C13 1.490(2) . ? N1 C7 1.491(2) . ? C14 N3 1.347(2) . ? C14 C15 1.392(2) . ? C14 C13 1.496(3) . ? N3 C18 1.349(2) . ? N2 C8 1.344(2) . ? N2 C12 1.348(2) . ? C1 C6 1.392(3) . ? C1 C2 1.391(2) . ? C8 C9 1.387(3) . ? C8 C7 1.499(2) . ? C18 C17 1.389(3) . ? C2 C3 1.396(3) . ? C3 C4 1.384(3) . ? C12 C11 1.384(3) . ? C9 C10 1.391(3) . ? C11 C10 1.386(4) . ? C4 C5 1.390(3) . ? C4 C19 1.518(3) . ? C17 C16 1.380(3) . ? C15 C16 1.388(3) . ? C6 C5 1.389(3) . ? C19 C20 1.510(3) . ? C20 N4 1.333(4) . ? C20 C21 1.367(4) . ? N4 C24 1.362(4) . ? C21 C22 1.377(5) . ? C24 C23 1.361(6) . ? C23 C22 1.355(6) . ? O1A S1A 1.5257(14) . ? O1A Cu1 2.3314(13) 2 ? O3A S1A 1.4701(16) . ? O2A S1A 1.4567(17) . ? O4A S1A 1.4586(16) . ? O4B O1B 0.940(15) 2_466 ? O4B S1B 1.482(8) . ? O3B S1B 1.354(8) . ? O1B O4B 0.940(15) 2_466 ? O1B S1B 1.616(10) . ? O1B S1B 2.018(16) 2_466 ? O2B S1B 1.434(10) . ? S1B O1B 2.018(16) 2_466 ? O3 O6 1.71(2) 2_556 ? O6 O3 1.71(2) 2_556 ? 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 O1A Cu1 N3 96.45(6) . . ? O1A Cu1 N2 98.51(6) . . ? N3 Cu1 N2 164.66(7) . . ? O1A Cu1 N1 177.81(6) . . ? N3 Cu1 N1 82.76(6) . . ? N2 Cu1 N1 82.17(6) . . ? O1A Cu1 O1A 78.73(5) . 2 ? N3 Cu1 O1A 93.16(6) . 2 ? N2 Cu1 O1A 93.07(6) . 2 ? N1 Cu1 O1A 103.33(5) . 2 ? C1 N1 C13 112.72(13) . . ? C1 N1 C7 111.12(14) . . ? C13 N1 C7 111.66(14) . . ? C1 N1 Cu1 111.03(11) . . ? C13 N1 Cu1 105.21(10) . . ? C7 N1 Cu1 104.64(10) . . ? N3 C14 C15 121.90(17) . . ? N3 C14 C13 115.96(15) . . ? C15 C14 C13 122.06(17) . . ? C14 N3 C18 119.41(16) . . ? C14 N3 Cu1 112.86(12) . . ? C18 N3 Cu1 127.59(13) . . ? C8 N2 C12 119.26(16) . . ? C8 N2 Cu1 112.50(12) . . ? C12 N2 Cu1 128.14(14) . . ? C6 C1 C2 119.77(17) . . ? C6 C1 N1 120.18(16) . . ? C2 C1 N1 120.03(15) . . ? N2 C8 C9 122.03(17) . . ? N2 C8 C7 115.76(15) . . ? C9 C8 C7 122.17(17) . . ? N1 C7 C8 109.32(14) . . ? N3 C18 C17 121.34(19) . . ? C1 C2 C3 119.65(18) . . ? N1 C13 C14 109.63(14) . . ? C4 C3 C2 121.14(19) . . ? N2 C12 C11 121.7(2) . . ? C8 C9 C10 118.6(2) . . ? C12 C11 C10 119.07(19) . . ? C3 C4 C5 118.35(18) . . ? C3 C4 C19 120.5(2) . . ? C5 C4 C19 121.0(2) . . ? C16 C17 C18 119.29(19) . . ? C16 C15 C14 118.48(19) . . ? C5 C6 C1 119.50(19) . . ? C11 C10 C9 119.27(19) . . ? C17 C16 C15 119.57(18) . . ? C6 C5 C4 121.5(2) . . ? C20 C19 C4 109.05(18) . . ? N4 C20 C21 119.8(3) . . ? N4 C20 C19 119.0(3) . . ? C21 C20 C19 121.1(3) . . ? C20 N4 C24 120.6(3) . . ? C20 C21 C22 119.8(4) . . ? N4 C24 C23 120.6(4) . . ? C22 C23 C24 119.1(3) . . ? C23 C22 C21 120.0(3) . . ? S1A O1A Cu1 118.48(8) . . ? S1A O1A Cu1 140.16(8) . 2 ? Cu1 O1A Cu1 101.27(5) . 2 ? O1B O4B S1B 110.9(12) 2_466 . ? O4B O1B S1B 148.9(14) 2_466 . ? O4B O1B S1B 43.3(9) 2_466 2_466 ? S1B O1B S1B 106.6(6) . 2_466 ? O4A S1A O2A 110.79(10) . . ? O4A S1A O3A 111.89(11) . . ? O2A S1A O3A 112.23(11) . . ? O4A S1A O1A 107.44(9) . . ? O2A S1A O1A 107.91(9) . . ? O3A S1A O1A 106.29(9) . . ? O3B S1B O2B 109.8(7) . . ? O3B S1B O4B 112.9(5) . . ? O2B S1B O4B 112.1(8) . . ? O3B S1B O1B 113.5(6) . . ? O2B S1B O1B 109.2(7) . . ? O4B S1B O1B 98.9(6) . . ? O3B S1B O1B 119.8(5) . 2_466 ? O2B S1B O1B 124.4(8) . 2_466 ? O4B S1B O1B 25.8(5) . 2_466 ? O1B S1B O1B 73.4(6) . 2_466 ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 32.68 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.660 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.134 # Attachment 'structure__8_.cif' data_c:\gaelle~1\articl~2\struct~2\(8)-cu~1\ann4bsad _database_code_depnum_ccdc_archive 'CCDC 649303' _audit_creation_method SHELXL-97 _chemical_name_systematic ; none ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety 'C24 H22 Cl4 Cu2 N4 O2' _chemical_formula_sum 'C24 H22 Cl4 Cu2 N4 O2' _chemical_formula_weight 671.54 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.46750(10) _cell_length_b 12.8704(2) _cell_length_c 24.3518(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2653.86(7) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 27.9 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 2.036 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 13441 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.1034 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.88 _reflns_number_total 6213 _reflns_number_gt 4408 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _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 0.026(16) _refine_ls_number_reflns 6213 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0823 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1263 _refine_ls_wR_factor_gt 0.1026 _refine_ls_goodness_of_fit_ref 0.765 _refine_ls_restrained_S_all 0.765 _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 0.10687(7) 0.59573(4) 0.80235(2) 0.01614(15) Uani 1 1 d . . . Cu2 Cu 0.13525(7) 0.58346(4) 0.62648(3) 0.02025(16) Uani 1 1 d . . . Cl2 Cl -0.02034(15) 0.61013(9) 0.70296(5) 0.0213(3) Uani 1 1 d . . . Cl3 Cl 0.32396(17) 0.69953(10) 0.64007(6) 0.0280(3) Uani 1 1 d . . . Cl4 Cl 0.27136(17) 0.44313(9) 0.59983(6) 0.0268(3) Uani 1 1 d . . . Cl1 Cl 0.16895(17) 0.76273(9) 0.82105(6) 0.0243(3) Uani 1 1 d . . . N1 N 0.0891(5) 0.4358(3) 0.81141(16) 0.0148(9) Uani 1 1 d . . . C1 C 0.1696(6) 0.4035(3) 0.86213(19) 0.0147(10) Uani 1 1 d . . . N2 N -0.1066(5) 0.5941(3) 0.83731(16) 0.0167(8) Uani 1 1 d . . . C20 C -0.0486(6) 0.6112(4) 0.5256(2) 0.0189(11) Uani 1 1 d . . . C13 C 0.1663(6) 0.3960(4) 0.7612(2) 0.0184(11) Uani 1 1 d . . . H13A H 0.0958 0.4056 0.7292 0.022 Uiso 1 1 calc R . . H13B H 0.1887 0.3208 0.7652 0.022 Uiso 1 1 calc R . . N3 N 0.3122(5) 0.5553(3) 0.76955(17) 0.0179(9) Uani 1 1 d . . . C7 C -0.0845(5) 0.4121(4) 0.81311(19) 0.0171(10) Uani 1 1 d . . . H7B H -0.1236 0.4004 0.7753 0.021 Uiso 1 1 calc R . . H7A H -0.1022 0.3477 0.8344 0.021 Uiso 1 1 calc R . . C8 C -0.1748(6) 0.4996(4) 0.8388(2) 0.0192(11) Uani 1 1 d . . . C11 C -0.3315(7) 0.6655(4) 0.8830(2) 0.0267(13) Uani 1 1 d . . . H11 H -0.3830 0.7239 0.8988 0.032 Uiso 1 1 calc R . . N4 N -0.0431(5) 0.5611(3) 0.57443(16) 0.0179(9) Uani 1 1 d . . . C16 C 0.5780(7) 0.4781(4) 0.7189(2) 0.0274(13) Uani 1 1 d . . . H16 H 0.6695 0.4515 0.7012 0.033 Uiso 1 1 calc R . . C24 C -0.1596(7) 0.4951(4) 0.5884(2) 0.0241(12) Uani 1 1 d . . . H24 H -0.1520 0.4591 0.6223 0.029 Uiso 1 1 calc R . . C2 C 0.1689(7) 0.4680(4) 0.9080(2) 0.0215(12) Uani 1 1 d . . . H2 H 0.1146 0.5325 0.9065 0.026 Uiso 1 1 calc R . . C15 C 0.4499(6) 0.4156(4) 0.7277(2) 0.0239(12) Uani 1 1 d . . . H15 H 0.4527 0.3449 0.7165 0.029 Uiso 1 1 calc R . . C12 C -0.1836(7) 0.6756(4) 0.8589(2) 0.0235(12) Uani 1 1 d . . . H12 H -0.1355 0.7422 0.8575 0.028 Uiso 1 1 calc R . . C6 C 0.2472(7) 0.3093(4) 0.8662(2) 0.0233(12) Uani 1 1 d . . . H6 H 0.2462 0.2626 0.8359 0.028 Uiso 1 1 calc R . . C18 C 0.4377(6) 0.6147(4) 0.7608(2) 0.0248(13) Uani 1 1 d . . . H18 H 0.4334 0.6851 0.7724 0.030 Uiso 1 1 calc R . . C10 C -0.4014(7) 0.5698(4) 0.8836(2) 0.0283(13) Uani 1 1 d . . . H10 H -0.5035 0.5612 0.8992 0.034 Uiso 1 1 calc R . . C9 C -0.3228(6) 0.4857(4) 0.8614(2) 0.0211(12) Uani 1 1 d . . . H9 H -0.3702 0.4188 0.8616 0.025 Uiso 1 1 calc R . . C22 C -0.2971(7) 0.5299(5) 0.5053(2) 0.0330(15) Uani 1 1 d . . . H22 H -0.3842 0.5202 0.4812 0.040 Uiso 1 1 calc R . . C17 C 0.5728(6) 0.5803(4) 0.7360(2) 0.0277(13) Uani 1 1 d . . . H17 H 0.6603 0.6254 0.7307 0.033 Uiso 1 1 calc R . . C14 C 0.3171(6) 0.4546(4) 0.7527(2) 0.0175(11) Uani 1 1 d . . . C21 C -0.1761(7) 0.5960(4) 0.4909(2) 0.0282(13) Uani 1 1 d . . . H21 H -0.1802 0.6317 0.4567 0.034 Uiso 1 1 calc R . . O1 O 0.1446(7) 0.7111(3) 0.95074(19) 0.0515(13) Uani 1 1 d . . . O2 O 0.0791(6) 0.3350(4) 0.50175(19) 0.0512(13) Uani 1 1 d . . . C4 C 0.3276(6) 0.3464(4) 0.9589(2) 0.0183(11) Uani 1 1 d . . . C19 C 0.0815(7) 0.6844(4) 0.5110(2) 0.0230(12) Uani 1 1 d . . . H19A H 0.1566 0.6881 0.5421 0.028 Uiso 1 1 calc R . . H19B H 0.0363 0.7547 0.5058 0.028 Uiso 1 1 calc R . . C5 C 0.3265(7) 0.2821(4) 0.9138(2) 0.0219(12) Uani 1 1 d . . . H5 H 0.3812 0.2177 0.9154 0.026 Uiso 1 1 calc R . . C3 C 0.2455(7) 0.4398(4) 0.9555(2) 0.0276(13) Uani 1 1 d . . . H3 H 0.2425 0.4847 0.9864 0.033 Uiso 1 1 calc R . . C23 C -0.2915(7) 0.4773(5) 0.5551(2) 0.0334(14) Uani 1 1 d . . . H23 H -0.3734 0.4313 0.5660 0.040 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 0.0137(3) 0.0133(3) 0.0215(3) -0.0009(2) 0.0018(2) -0.0002(2) Cu2 0.0162(3) 0.0210(3) 0.0235(3) 0.0007(3) 0.0009(3) 0.0012(3) Cl2 0.0163(6) 0.0279(6) 0.0197(7) 0.0025(5) 0.0008(5) 0.0028(5) Cl3 0.0198(7) 0.0236(6) 0.0406(8) -0.0014(6) 0.0008(6) -0.0041(5) Cl4 0.0260(7) 0.0236(6) 0.0307(7) -0.0027(6) -0.0004(6) 0.0065(5) Cl1 0.0271(7) 0.0149(6) 0.0310(7) -0.0046(5) 0.0032(6) -0.0041(5) N1 0.014(2) 0.0151(18) 0.015(2) -0.0033(16) -0.0006(17) -0.0017(16) C1 0.012(2) 0.015(2) 0.017(2) -0.002(2) -0.0012(19) -0.005(2) N2 0.013(2) 0.0194(19) 0.018(2) -0.0017(17) 0.0018(17) 0.0038(19) C20 0.021(3) 0.020(2) 0.016(3) -0.005(2) 0.005(2) 0.008(2) C13 0.021(3) 0.018(2) 0.016(2) -0.003(2) -0.003(2) 0.003(2) N3 0.016(2) 0.018(2) 0.020(2) 0.0025(18) -0.0010(18) 0.0024(17) C7 0.014(2) 0.021(2) 0.017(3) -0.003(2) -0.0008(19) -0.003(2) C8 0.019(3) 0.021(3) 0.018(3) 0.007(2) -0.007(2) -0.002(2) C11 0.023(3) 0.025(3) 0.032(3) 0.000(2) 0.008(3) 0.010(2) N4 0.017(2) 0.021(2) 0.016(2) 0.0020(18) 0.0040(18) 0.0047(18) C16 0.019(3) 0.039(3) 0.024(3) 0.010(3) 0.003(2) 0.012(2) C24 0.023(3) 0.031(3) 0.018(3) 0.003(2) 0.007(2) -0.007(2) C2 0.026(3) 0.016(2) 0.022(3) -0.005(2) 0.001(2) 0.012(2) C15 0.023(3) 0.024(3) 0.025(3) 0.002(2) -0.001(2) 0.005(2) C12 0.029(3) 0.017(3) 0.024(3) 0.002(2) -0.002(2) 0.002(2) C6 0.033(3) 0.021(2) 0.016(3) -0.008(2) 0.001(2) 0.000(2) C18 0.018(3) 0.023(3) 0.033(3) 0.003(2) 0.006(2) -0.002(2) C10 0.016(3) 0.039(3) 0.031(3) 0.001(3) 0.008(2) 0.004(2) C9 0.017(3) 0.022(2) 0.025(3) 0.004(2) 0.003(2) -0.004(2) C22 0.025(3) 0.043(3) 0.032(3) -0.008(3) -0.012(3) 0.004(3) C17 0.015(3) 0.035(3) 0.033(3) 0.010(3) 0.005(2) 0.002(2) C14 0.015(3) 0.019(2) 0.018(3) 0.003(2) 0.000(2) 0.002(2) C21 0.035(3) 0.028(3) 0.021(3) 0.001(2) -0.001(2) 0.009(3) O1 0.070(4) 0.039(2) 0.046(3) -0.003(2) -0.002(3) 0.009(2) O2 0.055(3) 0.056(3) 0.042(3) -0.005(2) -0.001(3) -0.007(3) C4 0.019(3) 0.018(2) 0.018(3) 0.000(2) 0.003(2) -0.006(2) C19 0.032(3) 0.020(3) 0.017(3) -0.003(2) 0.005(2) 0.000(2) C5 0.028(3) 0.016(2) 0.022(3) -0.002(2) -0.003(2) 0.003(2) C3 0.038(4) 0.023(3) 0.021(3) -0.004(2) -0.003(3) 0.005(3) C23 0.023(3) 0.042(3) 0.036(4) -0.006(3) 0.009(3) -0.008(3) _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 1.983(4) . ? Cu1 N2 1.998(4) . ? Cu1 N1 2.076(4) . ? Cu1 Cl1 2.2591(13) . ? Cu1 Cl2 2.6558(14) . ? Cu2 N4 1.993(4) . ? Cu2 Cl3 2.2123(14) . ? Cu2 Cl4 2.2387(14) . ? Cu2 Cl2 2.3068(14) . ? N1 C1 1.471(6) . ? N1 C13 1.478(6) . ? N1 C7 1.502(6) . ? C1 C6 1.383(7) . ? C1 C2 1.393(7) . ? N2 C12 1.342(6) . ? N2 C8 1.346(6) . ? C20 N4 1.354(6) . ? C20 C21 1.385(8) . ? C20 C19 1.492(7) . ? C13 C14 1.498(7) . ? N3 C18 1.325(7) . ? N3 C14 1.360(6) . ? C7 C8 1.498(7) . ? C8 C9 1.380(7) . ? C11 C10 1.366(7) . ? C11 C12 1.390(8) . ? N4 C24 1.345(7) . ? C16 C15 1.368(7) . ? C16 C17 1.381(8) . ? C24 C23 1.400(8) . ? C2 C3 1.374(7) . ? C15 C14 1.373(7) . ? C6 C5 1.386(7) . ? C18 C17 1.367(7) . ? C10 C9 1.381(7) . ? C22 C21 1.378(8) . ? C22 C23 1.389(9) . ? C4 C5 1.374(7) . ? C4 C3 1.390(7) . ? C4 C19 1.538(7) 2_565 ? C19 C4 1.538(7) 2_564 ? 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 164.17(16) . . ? N3 Cu1 N1 81.15(16) . . ? N2 Cu1 N1 83.03(16) . . ? N3 Cu1 Cl1 97.28(12) . . ? N2 Cu1 Cl1 97.75(12) . . ? N1 Cu1 Cl1 159.88(12) . . ? N3 Cu1 Cl2 90.39(12) . . ? N2 Cu1 Cl2 91.27(12) . . ? N1 Cu1 Cl2 97.86(11) . . ? Cl1 Cu1 Cl2 102.22(5) . . ? N4 Cu2 Cl3 137.73(13) . . ? N4 Cu2 Cl4 95.13(12) . . ? Cl3 Cu2 Cl4 102.49(6) . . ? N4 Cu2 Cl2 95.85(12) . . ? Cl3 Cu2 Cl2 101.03(5) . . ? Cl4 Cu2 Cl2 130.40(5) . . ? Cu2 Cl2 Cu1 119.58(5) . . ? C1 N1 C13 113.1(4) . . ? C1 N1 C7 111.9(4) . . ? C13 N1 C7 112.6(4) . . ? C1 N1 Cu1 109.6(3) . . ? C13 N1 Cu1 103.0(3) . . ? C7 N1 Cu1 106.0(3) . . ? C6 C1 C2 117.9(5) . . ? C6 C1 N1 121.9(4) . . ? C2 C1 N1 120.3(4) . . ? C12 N2 C8 119.1(4) . . ? C12 N2 Cu1 126.7(4) . . ? C8 N2 Cu1 114.2(3) . . ? N4 C20 C21 119.8(5) . . ? N4 C20 C19 118.9(5) . . ? C21 C20 C19 121.3(5) . . ? N1 C13 C14 108.4(4) . . ? C18 N3 C14 118.5(5) . . ? C18 N3 Cu1 128.0(3) . . ? C14 N3 Cu1 113.5(3) . . ? C8 C7 N1 111.0(4) . . ? N2 C8 C9 121.2(5) . . ? N2 C8 C7 116.6(4) . . ? C9 C8 C7 122.2(4) . . ? C10 C11 C12 118.6(5) . . ? C24 N4 C20 119.8(5) . . ? C24 N4 Cu2 119.1(3) . . ? C20 N4 Cu2 121.1(4) . . ? C15 C16 C17 119.2(5) . . ? N4 C24 C23 122.8(5) . . ? C3 C2 C1 121.1(5) . . ? C16 C15 C14 120.3(5) . . ? N2 C12 C11 122.0(5) . . ? C1 C6 C5 120.7(5) . . ? N3 C18 C17 123.7(5) . . ? C11 C10 C9 119.5(5) . . ? C8 C9 C10 119.5(5) . . ? C21 C22 C23 119.9(6) . . ? C18 C17 C16 117.9(5) . . ? N3 C14 C15 120.5(5) . . ? N3 C14 C13 114.4(4) . . ? C15 C14 C13 125.1(4) . . ? C20 C21 C22 120.7(5) . . ? C5 C4 C3 118.1(5) . . ? C5 C4 C19 120.4(5) . 2_565 ? C3 C4 C19 121.5(5) . 2_565 ? C20 C19 C4 113.7(4) . 2_564 ? C4 C5 C6 121.3(5) . . ? C2 C3 C4 120.9(5) . . ? C24 C23 C22 117.0(5) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.88 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.541 _refine_diff_density_min -0.575 _refine_diff_density_rms 0.106 # Attachment 'structure__9_.cif' data_c:\gaelle~1\articl~2\struct~2\(9)-cu~1\ann6sad _database_code_depnum_ccdc_archive 'CCDC 649304' _audit_creation_method SHELXL-97 _chemical_name_systematic ; none ; _chemical_name_common none _chemical_melting_point - _chemical_formula_moiety 'C24.20 H22 Cl4 Cu2 N4 O0.20' _chemical_formula_sum 'C24.20 H22 Cl4 Cu2 N4 O0.20' _chemical_formula_weight 640.94 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' Cl Cl 0.1484 0.1585 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.5212(2) _cell_length_b 12.8596(3) _cell_length_c 24.1208(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2643.14(10) _cell_formula_units_Z 4 _cell_measurement_temperature 113(2) _cell_measurement_theta_max 27.9 _exptl_crystal_description plate _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1291 _exptl_absorpt_coefficient_mu 2.035 _exptl_absorpt_correction_type none _exptl_special_details ; none ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 15793 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0911 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 4.32 _diffrn_reflns_theta_max 27.85 _reflns_number_total 6143 _reflns_number_gt 4480 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius (2000)' _computing_cell_refinement 'Collect (Nonius (2000)' _computing_data_reduction 'Collect (Nonius (2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'WebLab ViewerPro (1997)' _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0395P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _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 0.018(13) _refine_ls_number_reflns 6143 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 0.977 _refine_ls_restrained_S_all 0.977 _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 0.38978(5) 0.09580(3) 0.200935(19) 0.01863(12) Uani 1 1 d . . . Cu2 Cu 0.36883(5) 0.07872(4) 0.37926(2) 0.02343(13) Uani 1 1 d . . . Cl2 Cl 0.51981(10) 0.10513(8) 0.30059(4) 0.0236(2) Uani 1 1 d . . . Cl3 Cl 0.18521(12) 0.19869(8) 0.36842(5) 0.0315(3) Uani 1 1 d . . . C1 C 0.3259(4) -0.0952(3) 0.13957(15) 0.0171(8) Uani 1 1 d . . . N2 N 0.6021(3) 0.0941(3) 0.16576(12) 0.0211(7) Uani 1 1 d . . . N1 N 0.4087(3) -0.0639(2) 0.19051(12) 0.0171(7) Uani 1 1 d . . . N3 N 0.1870(4) 0.0546(2) 0.23601(13) 0.0200(7) Uani 1 1 d . . . N4 N 0.5505(3) 0.0543(3) 0.42972(13) 0.0200(8) Uani 1 1 d . . . C18 C 0.0655(4) 0.1167(3) 0.24541(18) 0.0264(10) Uani 1 1 d . . . H18 H 0.0709 0.1877 0.2347 0.032 Uiso 1 1 calc R . . C12 C 0.6806(5) 0.1777(3) 0.14584(17) 0.0244(10) Uani 1 1 d . . . H12 H 0.6320 0.2442 0.1473 0.029 Uiso 1 1 calc R . . C13 C 0.3317(4) -0.1049(3) 0.24147(15) 0.0199(9) Uani 1 1 d . . . H13A H 0.4025 -0.0965 0.2737 0.024 Uiso 1 1 calc R . . H13B H 0.3084 -0.1798 0.2369 0.024 Uiso 1 1 calc R . . C15 C 0.0495(4) -0.0859(3) 0.27597(17) 0.0274(10) Uani 1 1 d . . . H15 H 0.0467 -0.1572 0.2864 0.033 Uiso 1 1 calc R . . C9 C 0.8212(5) -0.0136(3) 0.14235(17) 0.0263(10) Uani 1 1 d . . . H9 H 0.8690 -0.0804 0.1417 0.032 Uiso 1 1 calc R . . C17 C -0.0709(4) 0.0787(4) 0.27095(18) 0.0311(11) Uani 1 1 d . . . H17 H -0.1571 0.1237 0.2778 0.037 Uiso 1 1 calc R . . C8 C 0.6700(4) -0.0001(3) 0.16405(16) 0.0211(9) Uani 1 1 d . . . C7 C 0.5798(4) -0.0888(3) 0.18907(16) 0.0226(9) Uani 1 1 d . . . H7A H 0.5971 -0.1526 0.1669 0.027 Uiso 1 1 calc R . . H7B H 0.6179 -0.1020 0.2272 0.027 Uiso 1 1 calc R . . C6 C 0.2626(5) -0.1929(3) 0.13432(16) 0.0214(9) Uani 1 1 d . . . H6 H 0.2784 -0.2425 0.1630 0.026 Uiso 1 1 calc R . . C24 C 0.6635(5) -0.0144(3) 0.41494(18) 0.0322(11) Uani 1 1 d . . . H24 H 0.6500 -0.0531 0.3817 0.039 Uiso 1 1 calc R . . C22 C 0.8146(5) 0.0248(4) 0.49416(19) 0.0377(12) Uani 1 1 d . . . H22 H 0.9062 0.0159 0.5161 0.045 Uiso 1 1 calc R . . C11 C 0.8283(5) 0.1694(3) 0.12356(19) 0.0311(10) Uani 1 1 d . . . H11 H 0.8809 0.2289 0.1095 0.037 Uiso 1 1 calc R . . C20 C 0.5667(4) 0.1074(3) 0.47735(16) 0.0216(9) Uani 1 1 d . . . C21 C 0.6973(5) 0.0938(3) 0.51081(17) 0.0287(10) Uani 1 1 d . . . H21 H 0.7070 0.1311 0.5446 0.034 Uiso 1 1 calc R . . C16 C -0.0783(5) -0.0229(4) 0.28572(18) 0.0312(10) Uani 1 1 d . . . H16 H -0.1703 -0.0503 0.3025 0.037 Uiso 1 1 calc R . . C14 C 0.1813(4) -0.0452(3) 0.25110(15) 0.0196(9) Uani 1 1 d . . . C10 C 0.8990(5) 0.0725(3) 0.12199(17) 0.0337(11) Uani 1 1 d . . . H10 H 1.0014 0.0653 0.1069 0.040 Uiso 1 1 calc R . . C2 C 0.3103(5) -0.0257(3) 0.09615(17) 0.0252(10) Uani 1 1 d . . . H2 H 0.3567 0.0413 0.0986 0.030 Uiso 1 1 calc R . . Cl4 Cl 0.23483(12) -0.06110(8) 0.40611(5) 0.0332(3) Uani 1 1 d . . . Cl1 Cl 0.32422(12) 0.25986(7) 0.17852(5) 0.0293(3) Uani 1 1 d . . . C4 C 0.1552(4) -0.1518(3) 0.04453(16) 0.0204(9) Uani 1 1 d . . . C23 C 0.7962(5) -0.0304(4) 0.44565(19) 0.0365(12) Uani 1 1 d . . . H23 H 0.8739 -0.0785 0.4338 0.044 Uiso 1 1 calc R . . C3 C 0.2257(5) -0.0540(3) 0.04833(18) 0.0329(11) Uani 1 1 d . . . H3 H 0.2164 -0.0062 0.0185 0.039 Uiso 1 1 calc R . . C5 C 0.1760(5) -0.2206(3) 0.08784(16) 0.0227(9) Uani 1 1 d . . . H5 H 0.1305 -0.2880 0.0858 0.027 Uiso 1 1 calc R . . C19 C 0.4417(5) 0.1841(3) 0.49336(18) 0.0271(10) Uani 1 1 d . . . H19A H 0.3696 0.1936 0.4616 0.033 Uiso 1 1 calc R . . H19B H 0.4919 0.2521 0.5010 0.033 Uiso 1 1 calc R . . O1A O 0.0603(18) 0.1835(13) 0.0025(6) 0.039(4) Uani 0.20 1 d P . . C1A C -0.036(2) 0.2607(16) -0.0191(9) 0.025(5) Uiso 0.20 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 0.0140(2) 0.0158(2) 0.0260(3) 0.0003(2) 0.0013(2) 0.0002(2) Cu2 0.0160(2) 0.0262(3) 0.0281(3) -0.0014(2) 0.0000(2) -0.0007(2) Cl2 0.0151(4) 0.0325(5) 0.0233(5) -0.0046(5) 0.0000(4) -0.0039(4) Cl3 0.0220(5) 0.0287(6) 0.0440(7) 0.0005(5) 0.0005(5) 0.0043(5) C1 0.0122(16) 0.0193(19) 0.020(2) -0.0007(18) 0.0011(15) 0.0023(18) N2 0.0179(15) 0.0239(17) 0.0216(17) -0.0055(16) 0.0006(14) 0.0008(16) N1 0.0158(14) 0.0195(16) 0.0161(16) 0.0001(13) -0.0010(13) 0.0039(14) N3 0.0182(16) 0.0215(18) 0.0203(17) -0.0018(15) -0.0008(15) -0.0032(15) N4 0.0164(16) 0.0223(18) 0.0214(19) -0.0011(16) 0.0047(14) 0.0030(15) C18 0.0169(19) 0.027(2) 0.036(3) -0.0037(19) -0.0018(18) 0.0049(18) C12 0.026(2) 0.020(2) 0.026(2) -0.0026(19) 0.0003(19) -0.0060(19) C13 0.0210(18) 0.018(2) 0.020(2) -0.0001(18) -0.0022(16) -0.0014(18) C15 0.029(2) 0.025(2) 0.028(2) -0.002(2) -0.0025(18) -0.016(2) C9 0.021(2) 0.032(2) 0.026(2) -0.012(2) 0.0005(18) -0.001(2) C17 0.0125(18) 0.042(3) 0.039(3) -0.016(2) 0.0000(17) -0.002(2) C8 0.017(2) 0.025(2) 0.021(2) -0.0101(18) -0.0038(17) 0.0000(18) C7 0.0167(17) 0.022(2) 0.029(2) -0.0030(19) -0.0016(16) 0.0031(17) C6 0.031(2) 0.016(2) 0.017(2) 0.0024(18) -0.0047(18) 0.0013(18) C24 0.030(2) 0.039(3) 0.027(3) -0.008(2) 0.003(2) 0.013(2) C22 0.027(2) 0.054(3) 0.032(3) 0.012(3) -0.007(2) 0.001(2) C11 0.026(2) 0.033(2) 0.034(3) -0.001(2) 0.010(2) -0.012(2) C20 0.025(2) 0.022(2) 0.019(2) 0.0046(19) 0.0055(17) -0.0019(18) C21 0.033(2) 0.028(2) 0.025(2) 0.003(2) -0.0026(19) -0.008(2) C16 0.021(2) 0.043(3) 0.030(3) -0.006(2) 0.0033(19) -0.011(2) C14 0.0204(19) 0.022(2) 0.017(2) 0.0000(17) -0.0036(17) -0.0020(18) C10 0.0209(19) 0.049(3) 0.031(2) -0.011(2) 0.007(2) -0.002(2) C2 0.029(2) 0.018(2) 0.028(2) 0.0042(19) 0.001(2) -0.0071(19) Cl4 0.0321(5) 0.0302(6) 0.0375(6) 0.0025(5) -0.0016(5) -0.0086(5) Cl1 0.0308(5) 0.0180(5) 0.0389(6) 0.0058(5) 0.0051(5) 0.0047(5) C4 0.020(2) 0.023(2) 0.018(2) -0.0058(18) 0.0010(18) 0.0059(18) C23 0.025(2) 0.050(3) 0.034(3) 0.001(2) 0.004(2) 0.019(2) C3 0.049(3) 0.028(2) 0.021(2) 0.008(2) -0.006(2) 0.001(2) C5 0.033(2) 0.017(2) 0.019(2) 0.0015(18) -0.0003(18) -0.0029(19) C19 0.040(3) 0.021(2) 0.020(2) 0.0028(19) 0.0040(19) 0.001(2) O1A 0.049(10) 0.058(10) 0.009(8) 0.006(7) 0.014(7) -0.009(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 N3 1.995(3) . ? Cu1 N2 1.998(3) . ? Cu1 N1 2.075(3) . ? Cu1 Cl1 2.2484(10) . ? Cu1 Cl2 2.6496(10) . ? Cu2 N4 1.994(3) . ? Cu2 Cl3 2.2128(11) . ? Cu2 Cl4 2.2263(11) . ? Cu2 Cl2 2.3176(10) . ? C1 C6 1.373(5) . ? C1 C2 1.383(5) . ? C1 N1 1.473(5) . ? N2 C8 1.343(5) . ? N2 C12 1.355(5) . ? N1 C13 1.490(5) . ? N1 C7 1.493(4) . ? N3 C18 1.327(5) . ? N3 C14 1.335(5) . ? N4 C20 1.343(5) . ? N4 C24 1.355(5) . ? C18 C17 1.404(6) . ? C12 C11 1.372(6) . ? C13 C14 1.512(5) . ? C15 C16 1.378(6) . ? C15 C14 1.376(5) . ? C9 C10 1.382(6) . ? C9 C8 1.402(5) . ? C17 C16 1.356(6) . ? C8 C7 1.502(5) . ? C6 C5 1.389(6) . ? C24 C23 1.367(6) . ? C22 C23 1.377(7) . ? C22 C21 1.396(6) . ? C11 C10 1.384(6) . ? C20 C21 1.386(5) . ? C20 C19 1.503(5) . ? C2 C3 1.408(6) . ? C4 C5 1.381(5) . ? C4 C3 1.396(6) . ? C4 C19 1.542(6) 2_554 ? C19 C4 1.542(6) 2 ? O1A C1A 1.39(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 163.93(13) . . ? N3 Cu1 N1 81.71(12) . . ? N2 Cu1 N1 82.36(12) . . ? N3 Cu1 Cl1 97.82(10) . . ? N2 Cu1 Cl1 97.66(10) . . ? N1 Cu1 Cl1 156.74(9) . . ? N3 Cu1 Cl2 89.39(9) . . ? N2 Cu1 Cl2 90.41(9) . . ? N1 Cu1 Cl2 97.02(8) . . ? Cl1 Cu1 Cl2 106.24(4) . . ? N4 Cu2 Cl3 136.94(10) . . ? N4 Cu2 Cl4 95.36(10) . . ? Cl3 Cu2 Cl4 103.58(4) . . ? N4 Cu2 Cl2 95.28(9) . . ? Cl3 Cu2 Cl2 101.17(4) . . ? Cl4 Cu2 Cl2 129.89(4) . . ? Cu2 Cl2 Cu1 120.27(4) . . ? C6 C1 C2 118.9(3) . . ? C6 C1 N1 121.0(3) . . ? C2 C1 N1 120.1(3) . . ? C8 N2 C12 119.5(3) . . ? C8 N2 Cu1 114.4(3) . . ? C12 N2 Cu1 126.1(3) . . ? C1 N1 C13 112.4(3) . . ? C1 N1 C7 113.0(3) . . ? C13 N1 C7 111.9(3) . . ? C1 N1 Cu1 109.5(2) . . ? C13 N1 Cu1 102.5(2) . . ? C7 N1 Cu1 106.9(2) . . ? C18 N3 C14 120.2(3) . . ? C18 N3 Cu1 126.0(3) . . ? C14 N3 Cu1 113.8(3) . . ? C20 N4 C24 118.9(3) . . ? C20 N4 Cu2 121.5(3) . . ? C24 N4 Cu2 119.6(3) . . ? N3 C18 C17 120.7(4) . . ? N2 C12 C11 122.0(4) . . ? N1 C13 C14 108.7(3) . . ? C16 C15 C14 119.7(4) . . ? C10 C9 C8 118.3(4) . . ? C16 C17 C18 119.3(4) . . ? N2 C8 C9 121.3(4) . . ? N2 C8 C7 116.9(3) . . ? C9 C8 C7 121.7(4) . . ? N1 C7 C8 110.3(3) . . ? C1 C6 C5 121.2(4) . . ? N4 C24 C23 122.9(4) . . ? C23 C22 C21 119.4(4) . . ? C12 C11 C10 118.7(4) . . ? N4 C20 C21 121.1(4) . . ? N4 C20 C19 118.7(3) . . ? C21 C20 C19 120.1(4) . . ? C20 C21 C22 119.1(4) . . ? C17 C16 C15 119.0(4) . . ? N3 C14 C15 121.0(4) . . ? N3 C14 C13 114.5(3) . . ? C15 C14 C13 124.4(3) . . ? C9 C10 C11 120.2(4) . . ? C1 C2 C3 120.2(4) . . ? C5 C4 C3 118.2(4) . . ? C5 C4 C19 120.1(4) . 2_554 ? C3 C4 C19 121.7(4) . 2_554 ? C24 C23 C22 118.5(4) . . ? C2 C3 C4 120.4(4) . . ? C4 C5 C6 120.9(4) . . ? C20 C19 C4 114.1(3) . 2 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.85 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.710 _refine_diff_density_min -0.435 _refine_diff_density_rms 0.097