# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2006 data_global #================================================================ _audit_creation_date 23-01-03 _journal_coden_Cambridge 440 loop_ _publ_author_name 'M. Hosseini' 'Sylvie Ferlay' 'Abdelaziz Jouaiti' 'Nathalie Kyritsakas' 'Jerome Pansanel' 'Jean-Marc Planeix' _publ_contact_author_name 'M. Hosseini' _publ_contact_author_address ; Laboratoire de Chimie de Coordination Organique Universite Louis Pasteur 4 rue Blaise Pascal 67000 Strasbourg ; _publ_contact_author_email HOSSEINI@CHIMIE.U-STRASBG.FR _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Molecular tectonics: generation of 1- and 2-D copper coordination networks by positional isomeric tectons based on phenylenediamine backbone bearing two isonicotinoyl moieties ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158-166. ; data_st1316 _database_code_depnum_ccdc_archive 'CCDC 299702' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C30 H36 Cu2 N4 O12 S2' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C30 H36 Cu2 N4 O12 S2' _chemical_formula_weight 835.85 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Cu ? 0.263 1.266 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 S ? 0.110 0.124 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 8.2271(2) _cell_length_b 14.3223(3) _cell_length_c 15.7025(4) _cell_angle_alpha 76.877(4) _cell_angle_beta 89.004(4) _cell_angle_gamma 82.816(4) _cell_volume 1787.66(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173 _cell_measurement_reflns_used 14823 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 30.1 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.55 _exptl_crystal_density_method none _exptl_crystal_F_000 860 _exptl_absorpt_coefficient_mu 1.372 _exptl_absorpt_correction_type refdelf_(Walker_&_Stuart,_1983) _exptl_absorpt_correction_T_min 0.9530 _exptl_absorpt_correction_T_max 1.0000 #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 14823 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 36. mm. Scan angle = 2.0 deg 1 scans of 80 sec per frame. Data collection was divided into 2 set(s) with the following starting angles and number of frames : Set 1 Theta = 8.80 Omega = 0.00 Kappa = 0.00 91 frames Set 2 Theta = -8.30 Kappa = 134.00 Phi = 0.00 25 frames Friedel pairs were averaged. Internal R = 0.04 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14823 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 30.06 _reflns_number_total 10400 _reflns_number_gt 6842 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 6842 _refine_ls_number_parameters 451 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.124 _refine_ls_R_factor_gt 0.076 _refine_ls_wR_factor_all 0.192 _refine_ls_wR_factor_ref 0.095 _refine_ls_goodness_of_fit_all 2.438 _refine_ls_goodness_of_fit_ref 1.149 _refine_ls_shift/su_max 0.018 _refine_ls_shift/esd_mean 0.001 _refine_diff_density_max 1.142 _refine_diff_density_min -0.353 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol CU1 0.94215(8) -0.48059(5) 1.57262(4) 0.0179(3) Uani ? ? Cu CU2 0.07611(9) -0.05046(5) 1.57117(4) 0.0193(3) Uani ? ? Cu N1 0.8624(6) -0.4367(4) 1.6903(3) 0.025(2) Uani ? ? N C1 0.788(1) -0.4928(5) 1.7535(4) 0.042(3) Uani ? ? C C2 0.747(1) -0.4688(5) 1.8331(5) 0.044(3) Uani ? ? C C3 0.7869(8) -0.3835(4) 1.8474(4) 0.025(3) Uani ? ? C C4 0.8592(9) -0.3236(5) 1.7806(4) 0.035(3) Uani ? ? C C5 0.8944(9) -0.3514(5) 1.7040(4) 0.036(3) Uani ? ? C C6 0.7469(8) -0.3487(4) 1.9305(4) 0.027(3) Uani ? ? C O1 0.7674(7) -0.2668(3) 1.9350(3) 0.036(2) Uani ? ? O N2 0.6869(7) -0.4133(4) 1.9959(3) 0.027(2) Uani ? ? N C7 0.6311(8) -0.3889(4) 2.0761(4) 0.026(3) Uani ? ? C C8 0.7023(9) -0.4438(5) 2.1556(4) 0.032(3) Uani ? ? C C9 0.6475(9) -0.4224(6) 2.2330(4) 0.037(3) Uani ? ? C C10 0.5270(9) -0.3485(6) 2.2347(4) 0.037(3) Uani ? ? C C11 0.4559(9) -0.2928(5) 2.1565(4) 0.034(3) Uani ? ? C C12 0.5071(8) -0.3143(4) 2.0770(4) 0.024(3) Uani ? ? C N3 0.4279(7) -0.2591(4) 1.9970(3) 0.026(2) Uani ? ? N C13 0.3415(8) -0.3019(4) 1.9486(4) 0.026(3) Uani ? ? C O2 0.3132(7) -0.3862(3) 1.9706(3) 0.039(2) Uani ? ? O C14 0.2826(8) -0.2409(5) 1.8614(4) 0.026(3) Uani ? ? C C15 0.3036(9) -0.2795(5) 1.7882(4) 0.028(3) Uani ? ? C C16 0.2500(8) -0.2230(5) 1.7077(4) 0.026(3) Uani ? ? C N4 0.1769(7) -0.1325(4) 1.6971(3) 0.029(3) Uani ? ? N C17 0.156(1) -0.0963(5) 1.7683(5) 0.043(4) Uani ? ? C C18 0.208(1) -0.1474(6) 1.8510(5) 0.045(4) Uani ? ? C O3 1.0512(6) -0.6091(3) 1.6301(3) 0.027(2) Uani ? ? O O4 0.7513(5) -0.5425(3) 1.5503(3) 0.029(2) Uani ? ? O O5 1.1538(5) -0.4281(3) 1.5761(3) 0.029(2) Uani ? ? O O6 0.8468(6) -0.3584(3) 1.4948(3) 0.026(2) Uani ? ? O C19 0.7389(7) -0.5734(4) 1.4826(4) 0.022(3) Uani ? ? C C20 0.5862(8) -0.6150(5) 1.4680(5) 0.032(3) Uani ? ? C C21 1.1336(7) -0.6624(4) 1.5869(4) 0.025(3) Uani ? ? C C22 1.2144(9) -0.7591(5) 1.6367(5) 0.032(3) Uani ? ? C O7 -0.1243(6) -0.1148(3) 1.5883(3) 0.036(2) Uani ? ? O O8 -0.0384(6) 0.0533(3) 1.6219(3) 0.029(2) Uani ? ? O O9 0.1712(6) -0.1398(3) 1.4993(3) 0.028(2) Uani ? ? O C23 -0.1356(8) 0.1240(4) 1.5810(4) 0.024(3) Uani ? ? C C24 -0.2155(9) 0.1943(5) 1.6325(5) 0.032(3) Uani ? ? C O10 0.2533(5) 0.0300(3) 1.5330(3) 0.032(2) Uani ? ? O C25 -0.2446(8) -0.0932(4) 1.5367(4) 0.029(3) Uani ? ? C C26 -0.3896(9) -0.1486(5) 1.5608(6) 0.044(4) Uani ? ? C S1 0.4365(5) 0.0783(2) 2.1874(2) 0.081(2) Uani ? ? S C27 0.240(2) 0.053(1) 2.193(1) 0.11(1) Uani ? ? C C28 0.512(2) -0.035(1) 2.256(1) 0.11(1) Uani ? ? C O11 0.494(1) 0.0702(6) 2.0872(7) 0.091(6) Uani ? ? O S2 0.9958(5) 0.1536(3) 0.9206(3) 0.121(3) Uani ? ? S O12 0.910(2) 0.1195(8) 0.860(1) 0.227(9) Uani ? ? O C29 1.192(2) 0.122(1) 0.914(1) 0.19(1) Uani ? ? C C30 0.994(2) 0.2777(9) 0.8817(9) 0.097(8) Uani ? ? C H1 0.7612 -0.5524 1.7443 0.0553 Uiso calc C1 H H2 0.6928 -0.5110 1.8766 0.0593 Uiso calc C2 H H3 0.8847 -0.2629 1.7877 0.0460 Uiso calc C4 H H4 0.9435 -0.3087 1.6584 0.0468 Uiso calc C5 H H5 0.7875 -0.4952 2.1557 0.0446 Uiso calc C8 H H6 0.6948 -0.4600 2.2865 0.0539 Uiso calc C9 H H7 0.4913 -0.3348 2.2890 0.0510 Uiso calc C10 H H8 0.3730 -0.2405 2.1573 0.0444 Uiso calc C11 H H9 0.3542 -0.3439 1.7932 0.0401 Uiso calc C15 H H10 0.2660 -0.2498 1.6577 0.0375 Uiso calc C16 H H11 0.1023 -0.0323 1.7619 0.0690 Uiso calc C17 H H12 0.1931 -0.1184 1.8998 0.0706 Uiso calc C18 H H13 0.5940 -0.6353 1.4143 0.0457 Uiso calc C20 H H14 0.5737 -0.6688 1.5146 0.0457 Uiso calc C20 H H15 0.4941 -0.5673 1.4656 0.0457 Uiso calc C20 H H16 1.2712 -0.7926 1.5972 0.0454 Uiso calc C22 H H17 1.2898 -0.7498 1.6783 0.0454 Uiso calc C22 H H18 1.1334 -0.7959 1.6661 0.0454 Uiso calc C22 H H19 -0.2793 0.2462 1.5941 0.0446 Uiso calc C24 H H20 -0.2841 0.1621 1.6757 0.0446 Uiso calc C24 H H21 -0.1333 0.2186 1.6599 0.0446 Uiso calc C24 H H22 -0.4694 -0.1290 1.5152 0.0581 Uiso calc C26 H H23 -0.3546 -0.2158 1.5690 0.0581 Uiso calc C26 H H24 -0.4359 -0.1357 1.6134 0.0581 Uiso calc C26 H H25 0.1974 0.0566 2.2487 0.1595 Uiso calc C27 H H26 0.1761 0.0993 2.1490 0.1595 Uiso calc C27 H H27 0.2367 -0.0096 2.1834 0.1595 Uiso calc C27 H H28 0.4832 -0.0348 2.3147 0.1712 Uiso calc C28 H H29 0.4657 -0.0848 2.2380 0.1712 Uiso calc C28 H H30 0.6280 -0.0450 2.2515 0.1712 Uiso calc C28 H H31 1.2484 0.1458 0.9555 0.2380 Uiso calc C29 H H32 1.2142 0.0539 0.9258 0.2380 Uiso calc C29 H H33 1.2279 0.1491 0.8568 0.2380 Uiso calc C29 H H34 1.0514 0.3028 0.9217 0.1228 Uiso calc C30 H H35 1.0458 0.2899 0.8264 0.1228 Uiso calc C30 H H36 0.8841 0.3080 0.8757 0.1228 Uiso calc C30 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol CU1 0.0194(3) 0.0187(3) 0.0157(3) -0.0005(2) 0.0018(2) -0.0046(2) Cu CU2 0.0220(3) 0.0179(3) 0.0184(3) 0.0003(3) -0.0038(3) 0.0023(2) Cu N1 0.029(2) 0.026(2) 0.020(2) -0.005(2) 0.007(2) -0.006(2) N C1 0.071(4) 0.031(3) 0.034(3) -0.027(3) 0.024(3) -0.017(2) C C2 0.075(5) 0.037(3) 0.030(3) -0.028(3) 0.025(3) -0.009(3) C C3 0.029(3) 0.025(3) 0.022(2) -0.003(2) 0.003(2) -0.005(2) C C4 0.055(4) 0.026(3) 0.031(3) -0.017(3) 0.018(3) -0.013(2) C C5 0.053(4) 0.029(3) 0.030(3) -0.015(3) 0.014(3) -0.010(2) C C6 0.034(3) 0.024(3) 0.023(2) -0.006(2) 0.005(2) -0.006(2) C O1 0.066(3) 0.026(2) 0.028(2) -0.015(2) 0.015(2) -0.010(2) O N2 0.040(3) 0.025(2) 0.020(2) -0.001(2) 0.006(2) -0.004(2) N C7 0.036(3) 0.028(3) 0.017(2) -0.009(2) 0.004(2) -0.002(2) C C8 0.041(4) 0.033(3) 0.025(3) -0.003(3) -0.005(3) 0.002(2) C C9 0.046(4) 0.058(4) 0.019(3) -0.016(3) -0.008(3) 0.000(3) C C10 0.045(4) 0.058(4) 0.019(2) -0.010(3) -0.001(3) -0.017(2) C C11 0.040(4) 0.042(3) 0.025(3) -0.006(3) 0.005(3) -0.014(2) C C12 0.033(3) 0.028(3) 0.015(2) -0.003(2) 0.001(2) -0.005(2) C N3 0.036(3) 0.023(2) 0.020(2) -0.002(2) -0.001(2) -0.005(2) N C13 0.037(3) 0.025(3) 0.019(2) 0.001(2) -0.001(2) -0.003(2) C O2 0.071(3) 0.025(2) 0.033(2) -0.013(2) -0.018(2) 0.004(2) O C14 0.037(3) 0.027(3) 0.018(2) 0.001(3) -0.002(2) 0.000(2) C C15 0.039(3) 0.023(3) 0.025(3) 0.006(3) -0.004(3) 0.001(2) C C16 0.041(3) 0.029(3) 0.016(2) 0.000(3) -0.005(2) -0.004(2) C N4 0.037(3) 0.031(3) 0.021(2) 0.006(2) -0.005(2) 0.001(2) N C17 0.088(6) 0.030(3) 0.031(3) 0.025(4) -0.010(4) -0.002(3) C C18 0.094(6) 0.039(4) 0.024(3) 0.019(4) -0.011(4) -0.008(3) C O3 0.038(2) 0.021(2) 0.024(2) 0.006(2) -0.003(2) -0.004(1) O O4 0.024(2) 0.032(2) 0.033(2) -0.005(2) 0.005(2) -0.011(2) O O5 0.025(2) 0.035(2) 0.028(2) -0.008(2) -0.000(2) -0.007(2) O O6 0.038(2) 0.019(2) 0.024(2) 0.007(2) -0.002(2) -0.002(2) O C19 0.021(3) 0.017(2) 0.030(3) -0.000(2) -0.003(2) 0.000(2) C C20 0.020(3) 0.032(3) 0.053(4) -0.007(2) -0.003(3) -0.007(3) C C21 0.024(3) 0.023(2) 0.028(3) -0.001(2) -0.009(2) -0.002(2) C C22 0.043(4) 0.020(3) 0.037(3) 0.005(3) -0.012(3) -0.001(2) C O7 0.035(2) 0.033(2) 0.039(2) -0.013(2) -0.001(2) 0.006(2) O O8 0.038(2) 0.027(2) 0.025(2) 0.008(2) -0.004(2) -0.002(2) O O9 0.040(2) 0.022(2) 0.024(2) 0.008(2) -0.007(2) -0.003(2) O C23 0.029(3) 0.018(2) 0.026(3) -0.007(2) 0.003(2) -0.003(2) C C24 0.039(4) 0.023(3) 0.038(3) 0.003(3) 0.002(3) -0.004(2) C O10 0.024(2) 0.034(2) 0.040(2) -0.010(2) -0.004(2) -0.002(2) O C25 0.025(3) 0.025(2) 0.040(3) -0.009(2) 0.007(2) -0.011(2) C C26 0.035(3) 0.036(3) 0.067(5) -0.019(3) 0.012(3) -0.013(3) C S1 0.109(2) 0.060(1) 0.082(2) -0.017(2) 0.020(2) -0.003(1) S C27 0.12(1) 0.070(7) 0.17(1) -0.037(6) 0.02(1) 0.015(8) C C28 0.16(1) 0.073(7) 0.13(1) -0.016(8) 0.03(1) 0.047(7) C O11 0.076(5) 0.071(5) 0.140(7) -0.006(4) 0.017(5) 0.024(5) O S2 0.100(2) 0.119(2) 0.149(3) -0.056(2) -0.033(2) 0.022(3) S O12 0.31(1) 0.118(7) 0.31(1) -0.094(6) -0.204(7) -0.008(7) O C29 0.14(1) 0.168(9) 0.31(1) -0.057(9) 0.11(1) -0.183(7) C C30 0.087(7) 0.108(7) 0.099(8) -0.052(5) -0.004(6) -0.022(6) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag CU1 N1 2.150(5) . . ? CU1 O3 1.967(4) . . ? CU1 O4 1.970(5) . . ? CU1 O5 1.987(4) . . ? CU1 O6 1.972(4) . . ? CU2 N4 2.176(5) . . ? CU2 O7 1.973(5) . . ? CU2 O8 1.973(5) . . ? CU2 O9 1.975(4) . . ? CU2 O10 1.972(4) . . ? N1 C1 1.321(8) . . ? N1 C5 1.345(8) . . ? C1 C2 1.39(1) . . ? C2 C3 1.37(1) . . ? C3 C4 1.374(9) . . ? C3 C6 1.516(8) . . ? C4 C5 1.367(9) . . ? C6 O1 1.224(8) . . ? C6 N2 1.349(8) . . ? N2 C7 1.435(8) . . ? C7 C8 1.408(9) . . ? C7 C12 1.385(9) . . ? C8 C9 1.38(1) . . ? C9 C10 1.36(1) . . ? C10 C11 1.40(1) . . ? C11 C12 1.397(8) . . ? C12 N3 1.442(8) . . ? N3 C13 1.339(8) . . ? C13 O2 1.228(8) . . ? C13 C14 1.500(8) . . ? C14 C15 1.384(9) . . ? C14 C18 1.38(1) . . ? C15 C16 1.383(8) . . ? C16 N4 1.334(8) . . ? N4 C17 1.34(1) . . ? C17 C18 1.38(1) . . ? O3 C21 1.262(8) . . ? O4 C19 1.250(8) . . ? C19 C20 1.498(9) . . ? C21 C22 1.507(8) . . ? O7 C25 1.252(8) . . ? O8 C23 1.264(7) . . ? C23 C24 1.511(9) . . ? C25 C26 1.510(9) . . ? S1 C27 1.69(2) . . ? S1 C28 1.77(1) . . ? S1 O11 1.66(1) . . ? S2 O12 1.41(1) . . ? S2 C29 1.63(2) . . ? S2 C30 1.74(1) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 CU1 O3 96.5(2) . . . ? N1 CU1 O4 99.4(2) . . . ? N1 CU1 O5 91.6(2) . . . ? N1 CU1 O6 94.0(2) . . . ? O3 CU1 O4 88.5(2) . . . ? O3 CU1 O5 89.0(2) . . . ? O3 CU1 O6 169.4(2) . . . ? O4 CU1 O5 168.9(2) . . . ? O4 CU1 O6 90.1(2) . . . ? O5 CU1 O6 90.5(2) . . . ? N4 CU2 O7 91.9(2) . . . ? N4 CU2 O8 93.0(2) . . . ? N4 CU2 O9 97.9(2) . . . ? N4 CU2 O10 99.5(2) . . . ? O7 CU2 O8 88.6(2) . . . ? O7 CU2 O9 90.7(2) . . . ? O7 CU2 O10 168.5(2) . . . ? O8 CU2 O9 169.1(2) . . . ? O8 CU2 O10 89.5(2) . . . ? O9 CU2 O10 89.1(2) . . . ? CU1 N1 C1 122.4(4) . . . ? CU1 N1 C5 120.4(4) . . . ? C1 N1 C5 117.1(5) . . . ? N1 C1 C2 123.2(6) . . . ? C1 C2 C3 118.9(6) . . . ? C2 C3 C4 117.9(6) . . . ? C2 C3 C6 123.9(6) . . . ? C4 C3 C6 118.1(6) . . . ? C3 C4 C5 120.0(6) . . . ? N1 C5 C4 122.8(6) . . . ? C3 C6 O1 120.5(5) . . . ? C3 C6 N2 115.2(5) . . . ? O1 C6 N2 124.2(6) . . . ? C6 N2 C7 122.0(5) . . . ? N2 C7 C8 118.9(6) . . . ? N2 C7 C12 121.5(5) . . . ? C8 C7 C12 119.6(6) . . . ? C7 C8 C9 119.4(7) . . . ? C8 C9 C10 121.6(6) . . . ? C9 C10 C11 119.8(6) . . . ? C10 C11 C12 119.8(7) . . . ? C7 C12 C11 119.8(6) . . . ? C7 C12 N3 120.8(5) . . . ? C11 C12 N3 119.3(6) . . . ? C12 N3 C13 120.3(5) . . . ? N3 C13 O2 124.3(6) . . . ? N3 C13 C14 115.7(6) . . . ? O2 C13 C14 119.9(6) . . . ? C13 C14 C15 119.1(6) . . . ? C13 C14 C18 122.5(6) . . . ? C15 C14 C18 118.4(6) . . . ? C14 C15 C16 119.1(6) . . . ? C15 C16 N4 123.0(6) . . . ? CU2 N4 C16 121.7(4) . . . ? CU2 N4 C17 120.6(5) . . . ? C16 N4 C17 117.4(5) . . . ? N4 C17 C18 123.3(7) . . . ? C14 C18 C17 118.8(7) . . . ? CU1 O3 C21 121.2(4) . . . ? CU1 O4 C19 121.9(4) . . . ? O4 C19 C20 118.9(6) . . . ? O3 C21 C22 117.4(6) . . . ? CU2 O7 C25 124.1(4) . . . ? CU2 O8 C23 125.4(4) . . . ? O8 C23 C24 117.3(6) . . . ? O7 C25 C26 117.1(6) . . . ? C27 S1 C28 93.6(8) . . . ? C27 S1 O11 104.0(8) . . . ? C28 S1 O11 105.2(7) . . . ? O12 S2 C29 110(1) . . . ? O12 S2 C30 107.6(8) . . . ? C29 S2 C30 98.0(9) . . . ? data_st1321 _database_code_depnum_ccdc_archive 'CCDC 299703' #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C28 H34 Cu2 N4 O12' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H34 Cu2 N4 O12' _chemical_formula_weight 745.68 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Cu ? 0.263 1.266 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,+y,1/2-z -x,-y,-z +x,-y,1/2+z 1/2+x,1/2+y,+z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 33.799(1) _cell_length_b 12.7452(5) _cell_length_c 8.5671(5) _cell_angle_alpha 90 _cell_angle_beta 95.297(5) _cell_angle_gamma 90 _cell_volume 3674.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 9707 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 30.0 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.35 _exptl_crystal_density_method none _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 1.216 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 9707 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 36. mm. Scan angle = 1.6 deg 1 scans of 60 sec per frame. Data collection was divided into 2 set(s) with the following starting angles and number of frames : Set 1 Theta = 8.80 Omega = 0.00 Kappa = 0.00 107 frames Set 2 Theta = -8.50 Kappa = 110.00 Phi = 0.00 30 frames Friedel pairs were averaged. Internal R = 0.04 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 9707 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 30.01 _reflns_number_total 5522 _reflns_number_gt 2314 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2314 _refine_ls_number_parameters 206 _refine_ls_number_restraints 6 _refine_ls_number_constraints 5 _refine_ls_R_factor_all 0.188 _refine_ls_R_factor_gt 0.105 _refine_ls_wR_factor_all 0.290 _refine_ls_wR_factor_ref 0.134 _refine_ls_goodness_of_fit_all 1.902 _refine_ls_goodness_of_fit_ref 1.252 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_mean 0.010 _refine_diff_density_max 1.037 _refine_diff_density_min -0.604 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol CU 0.28157(5) 0.2163(1) 0.5847(2) 0.0369(6) 1.000 Uani ? ? Cu O1 0.2989(3) 0.3633(6) 0.577(1) 0.053(5) 1.000 Uani ? ? O C1 0.2788(5) 0.4336(9) 0.508(1) 0.043(6) 1.000 Uani ? ? C C2 0.2947(5) 0.544(1) 0.518(2) 0.063(9) 1.000 Uani ? ? C O2 0.2547(3) 0.0797(6) 0.566(1) 0.053(5) 1.000 Uani ? ? O O3 0.3034(3) 0.1885(7) 0.383(1) 0.061(5) 1.000 Uani ? ? O C3 0.2836(4) 0.2089(9) 0.256(1) 0.042(6) 1.000 Uani ? ? C C4 0.3020(6) 0.182(1) 0.109(2) 0.061(8) 1.000 Uani ? ? C O4 0.2504(3) 0.2531(6) 0.7584(9) 0.042(4) 1.000 Uani ? ? O N1 0.3330(3) 0.1629(8) 0.736(1) 0.049(6) 1.000 Uani ? ? N C5 0.3623(6) 0.225(1) 0.790(3) 0.09(1) 1.000 Uani ? ? C C6 0.3940(5) 0.196(1) 0.893(3) 0.10(1) 1.000 Uani ? ? C C7 0.3952(4) 0.094(1) 0.942(2) 0.058(9) 1.000 Uani ? ? C C8 0.3653(4) 0.0274(9) 0.893(1) 0.042(6) 1.000 Uani ? ? C C9 0.3348(4) 0.0655(9) 0.793(1) 0.040(6) 1.000 Uani ? ? C C10 0.4271(5) 0.060(1) 1.069(3) 0.08(1) 1.000 Uani ? ? C O5 0.4331(4) 0.1162(9) 1.200(2) 0.12(1) 1.000 Uani ? ? O N2 0.4421(3) -0.0324(9) 1.053(2) 0.062(8) 1.000 Uani ? ? N C11 0.4719(4) -0.082(1) 1.158(3) 0.06(1) 1.000 Uani ? ? C C12 0.5000 -0.030(2) 1.2500 0.05(1) 0.500 Uani ? ? C C13 0.5287(8) -0.190(2) 1.346(3) 0.1518 1.000 Uani ? ? C C14 0.5000 -0.243(3) 1.2500 0.1330 0.500 Uani ? ? C O6 0.4179(8) 0.441(2) 0.395(3) 0.12(2) 1.000 Uani ? ? O C15 0.3881(8) 0.3618(2) 0.3623(3) 0.14(4) 1.000 Uani ? ? C H1 0.2765 0.5900 0.4606 0.0941 1.000 Uiso calc C2 H H2 0.2980 0.5658 0.6246 0.0941 1.000 Uiso calc C2 H H3 0.3196 0.5468 0.4750 0.0941 1.000 Uiso calc C2 H H4 0.2844 0.2011 0.0207 0.0972 1.000 Uiso calc C4 H H5 0.3263 0.2197 0.1065 0.0972 1.000 Uiso calc C4 H H6 0.3072 0.1090 0.1066 0.0972 1.000 Uiso calc C4 H H7 0.3615 0.2960 0.7550 0.1336 1.000 Uiso calc C5 H H8 0.4142 0.2442 0.9282 0.1537 1.000 Uiso calc C6 H H9 0.3655 -0.0435 0.9277 0.0558 1.000 Uiso calc C8 H H10 0.3135 0.0194 0.7617 0.0528 1.000 Uiso calc C9 H H11 0.4324 -0.0714 0.9632 0.0975 1.000 Uiso calc N2 H H12 0.5000 0.0445 1.2500 0.0868 0.500 Uiso calc C12 H H13 0.5000 -0.3180 1.2500 0.1729 0.500 Uiso calc C14 H H14 0.5481 -0.2267 1.4123 0.1974 1.000 Uiso calc C13 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol CU 0.082(1) 0.0267(5) 0.0230(5) 0.0061(8) 0.0025(6) 0.0003(6) Cu O1 0.080(6) 0.032(4) 0.058(5) 0.001(4) 0.011(5) 0.007(4) O C1 0.10(1) 0.030(5) 0.028(5) -0.003(6) 0.009(6) -0.006(5) C C2 0.11(1) 0.030(6) 0.073(9) -0.005(8) -0.00(1) 0.002(7) C O2 0.127(8) 0.025(4) 0.046(5) -0.002(5) -0.022(5) 0.003(4) O O3 0.104(7) 0.068(6) 0.033(4) 0.039(5) 0.010(5) -0.002(4) O C3 0.10(1) 0.027(5) 0.026(5) 0.006(7) 0.016(6) -0.000(5) C C4 0.15(1) 0.037(6) 0.040(6) 0.019(8) 0.036(7) 0.006(5) C O4 0.082(6) 0.046(4) 0.019(3) 0.000(4) 0.006(4) -0.004(3) O N1 0.074(7) 0.037(5) 0.043(5) -0.005(6) 0.001(5) 0.003(5) N C5 0.11(1) 0.051(8) 0.14(2) -0.025(9) -0.02(1) 0.03(1) C C6 0.08(1) 0.072(9) 0.19(2) -0.042(8) -0.05(1) 0.05(1) C C7 0.041(8) 0.042(7) 0.11(1) -0.000(7) -0.019(8) 0.006(8) C C8 0.044(7) 0.030(5) 0.055(7) 0.003(5) 0.005(6) -0.004(5) C C9 0.051(7) 0.030(5) 0.041(6) 0.001(5) 0.004(6) -0.003(5) C C10 0.08(1) 0.033(7) 0.21(2) -0.013(8) -0.07(1) -0.02(1) C O5 0.123(9) 0.054(7) 0.24(1) 0.012(7) -0.107(9) -0.018(9) O N2 0.035(7) 0.050(6) 0.14(1) -0.004(6) -0.012(7) -0.019(7) N C11 0.030(7) 0.036(7) 0.22(2) -0.000(7) -0.04(1) -0.01(1) C C12 0.03(1) 0.04(1) 0.13(2) 0.0000 0.00(1) 0.0000 C C13 0.1518 0.15(2) 0.15(2) 0.00(2) 0.01(2) 0.00(2) C C14 0.1330 0.13(3) 0.13(3) 0.0000 0.01(2) 0.0000 C O6 0.12(2) 0.12(2) 0.12(2) 0.00(2) 0.01(2) 0.00(2) O C15 0.14(4) 0.14(4) 0.14(4) 0.00(4) 0.01(3) 0.00(4) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag CU O1 1.966(8) . . ? CU O2 1.963(9) . . ? CU O3 1.970(9) . . ? CU O4 1.957(9) . . ? CU N1 2.18(1) . . ? O1 C1 1.24(2) . . ? C1 C2 1.51(2) . . ? C1 O2 1.26(2) . 7_556 ? O3 C3 1.26(2) . . ? C3 C4 1.49(2) . . ? C3 O4 1.24(2) . 7_556 ? N1 C5 1.32(2) . . ? N1 C9 1.33(1) . . ? C5 C6 1.37(3) . . ? C6 C7 1.36(2) . . ? C7 C8 1.36(2) . . ? C7 C10 1.52(2) . . ? C8 C9 1.37(2) . . ? C10 O5 1.33(3) . . ? C10 N2 1.30(2) . . ? N2 C11 1.43(2) . . ? C11 C12 1.35(2) . . ? C13 C14 1.39(3) . . ? O6 C15 1.43(3) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 CU O2 168.4(4) . . . ? O1 CU O3 90.3(4) . . . ? O1 CU O4 88.9(4) . . . ? O1 CU N1 95.4(4) . . . ? O2 CU O3 88.7(4) . . . ? O2 CU O4 89.9(4) . . . ? O2 CU N1 96.2(4) . . . ? O3 CU O4 168.6(4) . . . ? O3 CU N1 96.9(4) . . . ? O4 CU N1 94.5(4) . . . ? CU O1 C1 123.4(9) . . . ? O1 C1 C2 118(1) . . . ? O1 C1 O2 124(1) . . 7_556 ? C2 C1 O2 117(1) . . 7_556 ? CU O2 C1 123.2(8) . . 7_556 ? CU O3 C3 120.8(9) . . . ? O3 C3 C4 117(1) . . . ? O3 C3 O4 125(1) . . 7_556 ? C4 C3 O4 117(1) . . 7_556 ? CU O4 C3 125.3(7) . . 7_556 ? CU N1 C5 123(1) . . . ? CU N1 C9 121.1(9) . . . ? C5 N1 C9 114(1) . . . ? N1 C5 C6 125(1) . . . ? C5 C6 C7 117(1) . . . ? C6 C7 C8 120(1) . . . ? C6 C7 C10 119(1) . . . ? C8 C7 C10 119(1) . . . ? C7 C8 C9 117(1) . . . ? N1 C9 C8 124(1) . . . ? C7 C10 O5 119(1) . . . ? C7 C10 N2 116(1) . . . ? O5 C10 N2 122(1) . . . ? C10 N2 C11 126(1) . . . ? N2 C11 C12 124(1) . . . ? data_e512a _database_code_depnum_ccdc_archive 'CCDC 299704' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H20 Cu N4 O6' _chemical_formula_sum 'C22 H20 Cu N4 O6' _chemical_formula_weight 499.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n _symmetry_space_group_name_Hall '-P 2yn' 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 13.6671(13) _cell_length_b 11.5908(8) _cell_length_c 14.1521(16) _cell_angle_alpha 90.00 _cell_angle_beta 117.785(3) _cell_angle_gamma 90.00 _cell_volume 1983.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7007 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.41 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.674 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 1.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8460 _exptl_absorpt_correction_T_max 0.8460 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _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_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18010 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 27.15 _reflns_number_total 4373 _reflns_number_gt 3714 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+2.3824P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4373 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0440 _refine_ls_R_factor_gt 0.0349 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0872 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.001 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 0.54387(2) 0.86310(2) 0.047286(19) 0.01725(9) Uani 1 1 d . . . N1 N 0.58205(15) 0.90981(17) 0.19864(13) 0.0187(4) Uani 1 1 d . . . C1 C 0.50902(19) 0.9427(2) 0.23176(17) 0.0221(5) Uani 1 1 d . . . H1 H 0.4334 0.9494 0.1804 0.026 Uiso 1 1 calc R . . C2 C 0.53911(19) 0.9676(2) 0.33797(17) 0.0222(5) Uani 1 1 d . . . H2 H 0.4854 0.9918 0.3586 0.027 Uiso 1 1 calc R . . C3 C 0.64945(19) 0.9563(2) 0.41323(16) 0.0200(4) Uani 1 1 d . . . C4 C 0.7249(2) 0.9248(2) 0.37854(17) 0.0255(5) Uani 1 1 d . . . H4 H 0.8013 0.9189 0.4278 0.031 Uiso 1 1 calc R . . C5 C 0.6881(2) 0.9019(2) 0.27132(18) 0.0250(5) Uani 1 1 d . . . H5 H 0.7407 0.8797 0.2485 0.030 Uiso 1 1 calc R . . C6 C 0.68246(19) 0.9816(2) 0.52904(17) 0.0228(5) Uani 1 1 d . . . O1 O 0.63330(16) 1.05283(18) 0.55341(13) 0.0373(5) Uani 1 1 d . . . N2 N 0.76878(16) 0.91725(18) 0.59891(14) 0.0241(4) Uani 1 1 d . . . H2A H 0.8031 0.8759 0.5712 0.029 Uiso 1 1 calc R . . C7 C 0.81064(19) 0.9083(2) 0.71100(16) 0.0213(5) Uani 1 1 d . . . C8 C 0.7843(2) 0.9838(2) 0.77181(17) 0.0233(5) Uani 1 1 d . . . H8 H 0.7365 1.0475 0.7391 0.028 Uiso 1 1 calc R . . C9 C 0.3285(2) 0.5347(2) -0.61931(17) 0.0238(5) Uani 1 1 d . . . H9 H 0.3109 0.4825 -0.5777 0.029 Uiso 1 1 calc R . . C10 C 0.39777(19) 0.6275(2) -0.56927(17) 0.0205(5) Uani 1 1 d . . . C11 C 0.4262(2) 0.7011(2) -0.62995(18) 0.0262(5) Uani 1 1 d . . . H11 H 0.4750 0.7639 -0.5971 0.031 Uiso 1 1 calc R . . C12 C 0.8829(2) 0.8179(2) 0.76141(18) 0.0268(5) Uani 1 1 d . . . H12 H 0.9031 0.7677 0.7203 0.032 Uiso 1 1 calc R . . N3 N 0.43024(16) 0.64823(18) -0.46004(14) 0.0231(4) Uani 1 1 d . . . H3 H 0.3887 0.6178 -0.4342 0.028 Uiso 1 1 calc R . . C13 C 0.51905(19) 0.7104(2) -0.39155(17) 0.0226(5) Uani 1 1 d . . . O2 O 0.59266(14) 0.74551(17) -0.40955(13) 0.0318(4) Uani 1 1 d . . . C14 C 0.52026(19) 0.7362(2) -0.28589(16) 0.0209(5) Uani 1 1 d . . . C15 C 0.6219(2) 0.7429(2) -0.19410(18) 0.0255(5) Uani 1 1 d . . . H15 H 0.6886 0.7258 -0.1966 0.031 Uiso 1 1 calc R . . C16 C 0.6237(2) 0.7749(2) -0.09924(18) 0.0262(5) Uani 1 1 d . . . H16 H 0.6929 0.7766 -0.0363 0.031 Uiso 1 1 calc R . . N4 N 0.53235(16) 0.80371(17) -0.09165(14) 0.0208(4) Uani 1 1 d . . . C17 C 0.43446(19) 0.7961(2) -0.18049(17) 0.0223(5) Uani 1 1 d . . . H17 H 0.3690 0.8145 -0.1760 0.027 Uiso 1 1 calc R . . C18 C 0.42517(19) 0.7625(2) -0.27847(17) 0.0214(5) Uani 1 1 d . . . H18 H 0.3547 0.7575 -0.3395 0.026 Uiso 1 1 calc R . . O3 O 0.47701(14) 0.71702(14) 0.06627(12) 0.0238(3) Uani 1 1 d . . . C19 C 0.5583(2) 0.6488(2) 0.11468(18) 0.0235(5) Uani 1 1 d . . . O4 O 0.65499(15) 0.67544(17) 0.13903(16) 0.0352(4) Uani 1 1 d . . . C20 C 0.5326(2) 0.5304(2) 0.1430(2) 0.0322(6) Uani 1 1 d . . . H20A H 0.5919 0.4767 0.1525 0.048 Uiso 1 1 calc R . . H20B H 0.4623 0.5028 0.0854 0.048 Uiso 1 1 calc R . . H20C H 0.5271 0.5352 0.2095 0.048 Uiso 1 1 calc R . . O5 O 0.60891(14) 1.01459(14) 0.03076(12) 0.0236(4) Uani 1 1 d . . . C21 C 0.7076(2) 1.0193(2) 0.06222(17) 0.0240(5) Uani 1 1 d . . . O6 O 0.77265(15) 0.93573(16) 0.09751(13) 0.0297(4) Uani 1 1 d . . . C22 C 0.7596(2) 1.1377(2) 0.0661(2) 0.0355(6) Uani 1 1 d . . . H22A H 0.7047 1.1882 0.0117 0.053 Uiso 1 1 calc R . . H22B H 0.8230 1.1285 0.0522 0.053 Uiso 1 1 calc R . . H22C H 0.7844 1.1721 0.1369 0.053 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 0.02266(15) 0.01911(16) 0.00834(13) -0.00087(9) 0.00585(10) 0.00009(10) N1 0.0239(9) 0.0201(10) 0.0104(8) 0.0005(7) 0.0067(7) -0.0017(7) C1 0.0213(11) 0.0257(13) 0.0151(10) 0.0016(9) 0.0050(9) 0.0001(9) C2 0.0261(12) 0.0251(13) 0.0170(10) 0.0018(9) 0.0113(9) 0.0024(9) C3 0.0262(11) 0.0199(12) 0.0126(10) 0.0010(8) 0.0079(9) -0.0012(9) C4 0.0227(11) 0.0359(15) 0.0137(10) 0.0008(9) 0.0050(9) -0.0005(10) C5 0.0255(12) 0.0346(14) 0.0155(10) 0.0012(9) 0.0102(9) 0.0028(10) C6 0.0257(12) 0.0283(13) 0.0146(10) -0.0004(9) 0.0095(9) -0.0018(9) O1 0.0420(11) 0.0504(13) 0.0171(8) -0.0015(8) 0.0118(8) 0.0168(9) N2 0.0286(10) 0.0324(12) 0.0116(8) 0.0000(8) 0.0097(8) 0.0038(9) C7 0.0245(11) 0.0276(13) 0.0111(10) 0.0010(8) 0.0078(9) -0.0023(9) C8 0.0285(12) 0.0249(13) 0.0153(10) 0.0029(9) 0.0091(9) 0.0017(9) C9 0.0309(12) 0.0269(13) 0.0152(10) -0.0006(9) 0.0120(9) -0.0014(10) C10 0.0229(11) 0.0252(13) 0.0125(10) -0.0028(8) 0.0076(9) 0.0011(9) C11 0.0308(13) 0.0298(14) 0.0178(11) -0.0033(9) 0.0111(10) -0.0063(10) C12 0.0344(13) 0.0308(14) 0.0170(11) -0.0004(9) 0.0136(10) 0.0073(11) N3 0.0271(10) 0.0310(12) 0.0121(9) -0.0044(8) 0.0098(8) -0.0050(8) C13 0.0256(12) 0.0267(13) 0.0135(10) -0.0007(9) 0.0076(9) 0.0007(9) O2 0.0280(9) 0.0498(12) 0.0196(8) -0.0065(8) 0.0127(7) -0.0093(8) C14 0.0268(12) 0.0218(12) 0.0134(10) -0.0036(8) 0.0088(9) -0.0033(9) C15 0.0229(12) 0.0332(14) 0.0196(11) -0.0062(10) 0.0094(9) -0.0002(10) C16 0.0241(12) 0.0334(14) 0.0151(10) -0.0040(9) 0.0041(9) 0.0025(10) N4 0.0267(10) 0.0232(11) 0.0105(8) -0.0030(7) 0.0069(7) -0.0024(8) C17 0.0237(11) 0.0249(13) 0.0189(10) -0.0035(9) 0.0105(9) -0.0025(9) C18 0.0212(11) 0.0248(13) 0.0138(10) -0.0027(8) 0.0045(8) -0.0029(9) O3 0.0278(9) 0.0250(9) 0.0154(7) 0.0004(6) 0.0075(7) 0.0010(7) C19 0.0298(12) 0.0230(13) 0.0193(11) -0.0021(9) 0.0128(10) -0.0011(9) O4 0.0273(10) 0.0331(11) 0.0428(11) 0.0011(8) 0.0144(8) -0.0007(8) C20 0.0338(14) 0.0288(15) 0.0335(14) 0.0069(11) 0.0153(12) 0.0028(11) O5 0.0330(9) 0.0215(9) 0.0129(7) -0.0008(6) 0.0079(7) -0.0025(7) C21 0.0432(15) 0.0221(13) 0.0121(10) 0.0037(8) 0.0175(10) 0.0141(10) O6 0.0317(9) 0.0343(11) 0.0243(8) 0.0017(7) 0.0141(7) 0.0066(8) C22 0.0335(14) 0.0340(16) 0.0395(15) -0.0022(12) 0.0174(12) -0.0018(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 Cu1 O3 2.0007(17) . ? Cu1 N4 2.0189(18) . ? Cu1 N1 2.0276(17) . ? Cu1 O5 2.0303(17) . ? Cu1 O5 2.3322(17) 3_675 ? N1 C5 1.333(3) . ? N1 C1 1.341(3) . ? C1 C2 1.391(3) . ? C1 H1 0.9500 . ? C2 C3 1.389(3) . ? C2 H2 0.9500 . ? C3 C4 1.382(3) . ? C3 C6 1.512(3) . ? C4 C5 1.384(3) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 O1 1.211(3) . ? C6 N2 1.356(3) . ? N2 C7 1.417(3) . ? N2 H2A 0.8800 . ? C7 C8 1.388(3) . ? C7 C12 1.388(3) . ? C8 C9 1.385(3) 4_677 ? C8 H8 0.9500 . ? C9 C8 1.385(3) 4_574 ? C9 C10 1.389(3) . ? C9 H9 0.9500 . ? C10 C11 1.388(3) . ? C10 N3 1.416(3) . ? C11 C12 1.383(3) 4_574 ? C11 H11 0.9500 . ? C12 C11 1.383(3) 4_677 ? C12 H12 0.9500 . ? N3 C13 1.354(3) . ? N3 H3 0.8800 . ? C13 O2 1.217(3) . ? C13 C14 1.518(3) . ? C14 C18 1.386(3) . ? C14 C15 1.393(3) . ? C15 C16 1.382(3) . ? C15 H15 0.9500 . ? C16 N4 1.344(3) . ? C16 H16 0.9500 . ? N4 C17 1.346(3) . ? C17 C18 1.388(3) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? O3 C19 1.272(3) . ? C19 O4 1.239(3) . ? C19 C20 1.516(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O5 C21 1.209(3) . ? O5 Cu1 2.3323(17) 3_675 ? C21 O6 1.250(3) . ? C21 C22 1.535(4) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? 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 O3 Cu1 N4 90.52(7) . . ? O3 Cu1 N1 89.59(7) . . ? N4 Cu1 N1 169.96(8) . . ? O3 Cu1 O5 177.85(7) . . ? N4 Cu1 O5 91.28(7) . . ? N1 Cu1 O5 88.85(7) . . ? O3 Cu1 O5 102.35(6) . 3_675 ? N4 Cu1 O5 95.73(7) . 3_675 ? N1 Cu1 O5 94.05(7) . 3_675 ? O5 Cu1 O5 76.30(7) . 3_675 ? C5 N1 C1 117.95(18) . . ? C5 N1 Cu1 116.65(15) . . ? C1 N1 Cu1 125.34(15) . . ? N1 C1 C2 122.9(2) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 118.5(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C4 C3 C2 118.4(2) . . ? C4 C3 C6 122.8(2) . . ? C2 C3 C6 118.8(2) . . ? C3 C4 C5 119.4(2) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 122.8(2) . . ? N1 C5 H5 118.6 . . ? C4 C5 H5 118.6 . . ? O1 C6 N2 125.2(2) . . ? O1 C6 C3 121.1(2) . . ? N2 C6 C3 113.7(2) . . ? C6 N2 C7 128.1(2) . . ? C6 N2 H2A 116.0 . . ? C7 N2 H2A 116.0 . . ? C8 C7 C12 119.1(2) . . ? C8 C7 N2 124.2(2) . . ? C12 C7 N2 116.7(2) . . ? C9 C8 C7 119.2(2) 4_677 . ? C9 C8 H8 120.4 4_677 . ? C7 C8 H8 120.4 . . ? C8 C9 C10 121.8(2) 4_574 . ? C8 C9 H9 119.1 4_574 . ? C10 C9 H9 119.1 . . ? C11 C10 C9 118.8(2) . . ? C11 C10 N3 122.4(2) . . ? C9 C10 N3 118.7(2) . . ? C12 C11 C10 119.5(2) 4_574 . ? C12 C11 H11 120.3 4_574 . ? C10 C11 H11 120.3 . . ? C11 C12 C7 121.6(2) 4_677 . ? C11 C12 H12 119.2 4_677 . ? C7 C12 H12 119.2 . . ? C13 N3 C10 126.29(19) . . ? C13 N3 H3 116.9 . . ? C10 N3 H3 116.9 . . ? O2 C13 N3 125.5(2) . . ? O2 C13 C14 120.6(2) . . ? N3 C13 C14 113.87(19) . . ? C18 C14 C15 118.66(19) . . ? C18 C14 C13 122.6(2) . . ? C15 C14 C13 118.6(2) . . ? C16 C15 C14 118.7(2) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? N4 C16 C15 123.2(2) . . ? N4 C16 H16 118.4 . . ? C15 C16 H16 118.4 . . ? C16 N4 C17 117.72(18) . . ? C16 N4 Cu1 120.59(15) . . ? C17 N4 Cu1 121.63(15) . . ? N4 C17 C18 122.7(2) . . ? N4 C17 H17 118.7 . . ? C18 C17 H17 118.7 . . ? C14 C18 C17 119.0(2) . . ? C14 C18 H18 120.5 . . ? C17 C18 H18 120.5 . . ? C19 O3 Cu1 105.03(15) . . ? O4 C19 O3 123.0(2) . . ? O4 C19 C20 120.0(2) . . ? O3 C19 C20 117.0(2) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C21 O5 Cu1 118.03(15) . . ? C21 O5 Cu1 138.26(16) . 3_675 ? Cu1 O5 Cu1 103.70(7) . 3_675 ? O5 C21 O6 125.1(2) . . ? O5 C21 C22 118.2(2) . . ? O6 C21 C22 116.6(2) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.928 _refine_diff_density_min -0.815 _refine_diff_density_rms 0.071