# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cu25-en_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H28 Cu N4 O14' _chemical_formula_weight 563.96 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.1562(13) _cell_length_b 7.2456(13) _cell_length_c 11.618(2) _cell_angle_alpha 82.299(10) _cell_angle_beta 89.056(10) _cell_angle_gamma 70.660(10) _cell_volume 563.03(17) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.663 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 293 _exptl_absorpt_coefficient_mu 1.051 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 3290 _diffrn_reflns_av_R_equivalents 0.0299 _diffrn_reflns_av_sigmaI/netI 0.0404 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 24.50 _reflns_number_total 1830 _reflns_number_gt 1466 _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^)+(0.0911P)^2^+0.0200P] 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 1830 _refine_ls_number_parameters 185 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_gt 0.0430 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.006 _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 C1 C 0.6888(5) 0.2111(6) 0.1775(3) 0.0274(8) Uani 1 1 d . . . C2 C 0.8514(5) 0.2247(5) 0.0953(3) 0.0239(8) Uani 1 1 d . . . C3 C 1.0497(5) 0.1197(5) 0.1173(3) 0.0269(8) Uani 1 1 d . . . H3 H 1.0915 0.0327 0.1856 0.032 Uiso 1 1 calc R . . C4 C 1.1853(5) 0.1458(5) 0.0363(3) 0.0280(8) Uani 1 1 d . . . H4 H 1.3200 0.0798 0.0506 0.034 Uiso 1 1 calc R . . C5 C 1.1185(5) 0.2714(5) -0.0665(3) 0.0227(8) Uani 1 1 d . . . C6 C 0.9169(5) 0.3709(5) -0.0829(3) 0.0231(8) Uani 1 1 d . . . H6 H 0.8711 0.4547 -0.1519 0.028 Uiso 1 1 calc R . . C7 C 1.2606(5) 0.3140(6) -0.1568(3) 0.0297(9) Uani 1 1 d . . . C8 C 0.5478(6) 0.4957(7) 0.4425(3) 0.0386(10) Uani 1 1 d . . . H8A H 0.6642 0.5354 0.4454 0.046 Uiso 1 1 calc R . . H8B H 0.5898 0.3612 0.4247 0.046 Uiso 1 1 calc R . . Cu1 Cu 0.5000 0.5000 0.0000 0.0281(3) Uani 1 2 d S . . H5A H 0.519(5) 0.008(8) 0.330(3) 0.066(15) Uiso 1 1 d D . . H6A H 0.234(9) 0.259(7) 0.377(7) 0.16(3) Uiso 1 1 d D . . H7A H 0.908(7) 0.886(10) 0.378(5) 0.11(2) Uiso 1 1 d D . . H6B H 0.024(5) 0.454(6) 0.338(3) 0.056(14) Uiso 1 1 d D . . H7B H 0.960(10) 0.770(10) 0.486(5) 0.13(3) Uiso 1 1 d D . . N1 N 0.7850(4) 0.3505(4) -0.0025(2) 0.0226(7) Uani 1 1 d . . . N2 N 0.4090(5) 0.6264(5) 0.3510(3) 0.0422(9) Uani 1 1 d . . . H2A H 0.3015 0.5909 0.3491 0.063 Uiso 1 1 calc R . . H2B H 0.4669 0.6171 0.2827 0.063 Uiso 1 1 calc R . . H2C H 0.3745 0.7504 0.3659 0.063 Uiso 1 1 calc R . . O1 O 0.5152(3) 0.3296(4) 0.1475(2) 0.0329(6) Uani 1 1 d . . . O2 O 0.7295(4) 0.0889(4) 0.2653(2) 0.0434(8) Uani 1 1 d . . . O3 O 1.1874(4) 0.4072(5) -0.2519(2) 0.0531(9) Uani 1 1 d . . . O4 O 1.4399(4) 0.2612(4) -0.1270(2) 0.0365(7) Uani 1 1 d . . . O5 O 0.4219(5) 0.0076(5) 0.3864(3) 0.0544(9) Uani 1 1 d D . . O6 O 0.1351(5) 0.3819(5) 0.3858(3) 0.0586(9) Uani 1 1 d D . . O7 O 1.0146(5) 0.8467(6) 0.4314(3) 0.0654(10) Uani 1 1 d D . . H5B H 0.493(12) 0.086(11) 0.412(8) 0.18(4) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0286(19) 0.031(2) 0.0230(19) 0.0021(15) 0.0036(14) -0.0126(15) C2 0.0266(18) 0.024(2) 0.0214(18) 0.0005(14) 0.0060(14) -0.0108(14) C3 0.0264(18) 0.031(2) 0.0196(18) 0.0068(15) 0.0005(14) -0.0091(15) C4 0.0250(19) 0.027(2) 0.029(2) -0.0003(15) 0.0025(15) -0.0064(15) C5 0.0226(17) 0.025(2) 0.0227(18) -0.0030(14) 0.0087(14) -0.0110(14) C6 0.0274(18) 0.026(2) 0.0164(17) 0.0015(14) 0.0040(13) -0.0113(14) C7 0.028(2) 0.032(2) 0.029(2) -0.0021(16) 0.0106(15) -0.0109(16) C8 0.034(2) 0.052(3) 0.027(2) 0.0000(17) 0.0092(17) -0.0130(18) Cu1 0.0200(4) 0.0376(5) 0.0210(4) 0.0089(3) 0.0058(2) -0.0070(3) N1 0.0234(14) 0.0262(17) 0.0195(15) 0.0019(12) 0.0041(11) -0.0120(12) N2 0.0371(19) 0.062(3) 0.0250(18) 0.0035(16) 0.0080(14) -0.0166(17) O1 0.0251(14) 0.0420(16) 0.0248(13) 0.0088(11) 0.0080(10) -0.0076(11) O2 0.0338(15) 0.052(2) 0.0318(16) 0.0214(13) 0.0058(11) -0.0083(13) O3 0.0304(15) 0.082(3) 0.0320(17) 0.0227(15) 0.0068(12) -0.0113(15) O4 0.0226(13) 0.0470(18) 0.0380(16) 0.0001(13) 0.0073(11) -0.0114(12) O5 0.053(2) 0.050(2) 0.057(2) 0.0037(16) 0.0233(16) -0.0174(16) O6 0.0408(19) 0.069(3) 0.055(2) -0.0017(17) -0.0063(15) -0.0051(17) O7 0.0433(19) 0.077(3) 0.057(2) 0.0160(19) -0.0016(17) -0.0044(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.227(4) . ? C1 O1 1.277(4) . ? C1 C2 1.514(5) . ? C2 N1 1.342(4) . ? C2 C3 1.379(5) . ? C3 C4 1.380(5) . ? C3 H3 0.9300 . ? C4 C5 1.387(5) . ? C4 H4 0.9300 . ? C5 C6 1.386(5) . ? C5 C7 1.521(5) . ? C6 N1 1.346(4) . ? C6 H6 0.9300 . ? C7 O3 1.239(5) . ? C7 O4 1.252(4) . ? C8 N2 1.467(5) . ? C8 C8 1.491(7) 2_666 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? Cu1 O1 1.955(3) . ? Cu1 O1 1.955(3) 2_665 ? Cu1 N1 1.969(3) 2_665 ? Cu1 N1 1.969(3) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? O5 H5A 0.949(12) . ? O5 H5B 0.949(12) . ? O6 H6A 0.952(15) . ? O6 H6B 0.938(14) . ? O7 H7A 0.93(2) . ? O7 H7B 0.95(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 O2 C1 O1 124.9(3) . . ? O2 C1 C2 119.4(3) . . ? O1 C1 C2 115.7(3) . . ? N1 C2 C3 122.4(3) . . ? N1 C2 C1 113.5(3) . . ? C3 C2 C1 124.1(3) . . ? C2 C3 C4 118.9(3) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 119.4(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? C6 C5 C4 118.4(3) . . ? C6 C5 C7 119.4(3) . . ? C4 C5 C7 122.0(3) . . ? N1 C6 C5 122.3(3) . . ? N1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? O3 C7 O4 125.4(4) . . ? O3 C7 C5 117.1(3) . . ? O4 C7 C5 117.5(3) . . ? N2 C8 C8 110.5(4) . 2_666 ? N2 C8 H8A 109.6 . . ? C8 C8 H8A 109.6 2_666 . ? N2 C8 H8B 109.6 . . ? C8 C8 H8B 109.6 2_666 . ? H8A C8 H8B 108.1 . . ? O1 Cu1 O1 180.00(9) . 2_665 ? O1 Cu1 N1 96.72(11) . 2_665 ? O1 Cu1 N1 83.28(11) 2_665 2_665 ? O1 Cu1 N1 83.28(11) . . ? O1 Cu1 N1 96.72(11) 2_665 . ? N1 Cu1 N1 180.0 2_665 . ? C2 N1 C6 118.5(3) . . ? C2 N1 Cu1 112.6(2) . . ? C6 N1 Cu1 128.7(2) . . ? C8 N2 H2A 109.5 . . ? C8 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C8 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C1 O1 Cu1 114.5(2) . . ? H5A O5 H5B 75(6) . . ? H6A O6 H6B 129(6) . . ? H7A O7 H7B 95(6) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 N1 174.0(3) . . . . ? O1 C1 C2 N1 -4.9(5) . . . . ? O2 C1 C2 C3 -6.2(6) . . . . ? O1 C1 C2 C3 174.9(3) . . . . ? N1 C2 C3 C4 0.5(5) . . . . ? C1 C2 C3 C4 -179.3(3) . . . . ? C2 C3 C4 C5 -2.1(5) . . . . ? C3 C4 C5 C6 1.7(5) . . . . ? C3 C4 C5 C7 177.1(3) . . . . ? C4 C5 C6 N1 0.4(5) . . . . ? C7 C5 C6 N1 -175.1(3) . . . . ? C6 C5 C7 O3 -13.7(5) . . . . ? C4 C5 C7 O3 170.9(4) . . . . ? C6 C5 C7 O4 162.7(3) . . . . ? C4 C5 C7 O4 -12.6(5) . . . . ? C3 C2 N1 C6 1.5(5) . . . . ? C1 C2 N1 C6 -178.6(3) . . . . ? C3 C2 N1 Cu1 -173.3(3) . . . . ? C1 C2 N1 Cu1 6.5(4) . . . . ? C5 C6 N1 C2 -2.0(5) . . . . ? C5 C6 N1 Cu1 171.9(2) . . . . ? O1 Cu1 N1 C2 -5.0(2) . . . . ? O1 Cu1 N1 C2 175.0(2) 2_665 . . . ? N1 Cu1 N1 C2 103(72) 2_665 . . . ? O1 Cu1 N1 C6 -179.2(3) . . . . ? O1 Cu1 N1 C6 0.8(3) 2_665 . . . ? N1 Cu1 N1 C6 -72(72) 2_665 . . . ? O2 C1 O1 Cu1 -178.1(3) . . . . ? C2 C1 O1 Cu1 0.7(4) . . . . ? O1 Cu1 O1 C1 -46(100) 2_665 . . . ? N1 Cu1 O1 C1 -177.8(3) 2_665 . . . ? N1 Cu1 O1 C1 2.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.555 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 942364' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_25pdccu-aba _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H44 Cu N6 O16' _chemical_formula_weight 784.23 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 P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 14.0765(7) _cell_length_b 9.4805(3) _cell_length_c 15.3959(6) _cell_angle_alpha 90.00 _cell_angle_beta 116.278(5) _cell_angle_gamma 90.00 _cell_volume 1842.29(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.414 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 822 _exptl_absorpt_coefficient_mu 0.670 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 6878 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0450 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3251 _reflns_number_gt 2458 _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^)+(0.0890P)^2^+1.6373P] 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 3251 _refine_ls_number_parameters 265 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0505 _refine_ls_wR_factor_ref 0.1596 _refine_ls_wR_factor_gt 0.1402 _refine_ls_goodness_of_fit_ref 0.955 _refine_ls_restrained_S_all 0.954 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4745(3) 0.2739(4) 0.5427(2) 0.0379(8) Uani 1 1 d . . . C2 C 0.4030(2) 0.2596(4) 0.4354(2) 0.0339(8) Uani 1 1 d . . . C3 C 0.3494(3) 0.3683(4) 0.3755(2) 0.0385(8) Uani 1 1 d . . . H3 H 0.3515 0.4584 0.4001 0.046 Uiso 1 1 calc R . . C4 C 0.2918(3) 0.3416(4) 0.2772(2) 0.0388(8) Uani 1 1 d . . . H4 H 0.2565 0.4147 0.2350 0.047 Uiso 1 1 calc R . . C5 C 0.2870(2) 0.2067(4) 0.2424(2) 0.0338(8) Uani 1 1 d . . . C6 C 0.3428(2) 0.1016(4) 0.3076(2) 0.0348(8) Uani 1 1 d . . . H6 H 0.3402 0.0100 0.2849 0.042 Uiso 1 1 calc R . . C7 C 0.2268(2) 0.1709(4) 0.1357(2) 0.0380(8) Uani 1 1 d . . . C8 C 0.5430(3) 0.6216(5) 0.9119(3) 0.0490(10) Uani 1 1 d . . . H8A H 0.5586 0.6845 0.9662 0.059 Uiso 1 1 calc R . . H8B H 0.4922 0.5521 0.9116 0.059 Uiso 1 1 calc R . . C9 C 0.4942(3) 0.7049(4) 0.8198(2) 0.0397(8) Uani 1 1 d . . . C10 C 0.4467(3) 0.6393(4) 0.7301(3) 0.0408(8) Uani 1 1 d . . . H10 H 0.4454 0.5413 0.7272 0.049 Uiso 1 1 calc R . . C11 C 0.4012(3) 0.7154(4) 0.6451(3) 0.0411(8) Uani 1 1 d . . . H11 H 0.3709 0.6686 0.5860 0.049 Uiso 1 1 calc R . . C12 C 0.4007(3) 0.8622(4) 0.6476(2) 0.0377(8) Uani 1 1 d . . . C13 C 0.4479(3) 0.9293(4) 0.7364(3) 0.0437(9) Uani 1 1 d . . . H13 H 0.4487 1.0273 0.7392 0.052 Uiso 1 1 calc R . . C14 C 0.4940(3) 0.8515(4) 0.8210(3) 0.0438(9) Uani 1 1 d . . . H14 H 0.5255 0.8984 0.8801 0.053 Uiso 1 1 calc R . . Cu1 Cu 0.5000 0.0000 0.5000 0.0480(3) Uani 1 2 d S . . H6OA H 0.808(4) 0.118(3) 0.832(4) 0.100(19) Uiso 1 1 d D . . H7OA H 0.581(3) 0.207(6) 0.959(2) 0.11(2) Uiso 1 1 d D . . H8OA H 0.566(3) 0.356(6) 0.720(2) 0.096(18) Uiso 1 1 d D . . H6OB H 0.853(9) 0.281(10) 0.850(8) 0.36(8) Uiso 1 1 d D . . H7OB H 0.560(4) 0.242(6) 0.859(4) 0.11(2) Uiso 1 1 d D . . H8OB H 0.679(3) 0.284(6) 0.794(5) 0.14(3) Uiso 1 1 d D . . N1 N 0.4003(2) 0.1275(3) 0.40191(18) 0.0352(6) Uani 1 1 d . . . N2 N 0.6418(2) 0.5484(3) 0.9255(2) 0.0397(7) Uani 1 1 d . . . H2A H 0.6270 0.4852 0.8785 0.060 Uiso 1 1 calc R . . H2B H 0.6698 0.5049 0.9826 0.060 Uiso 1 1 calc R . . H2C H 0.6878 0.6112 0.9235 0.060 Uiso 1 1 calc R . . N3 N 0.3569(2) 0.9402(4) 0.5612(2) 0.0483(8) Uani 1 1 d . . . H3A H 0.3592 1.0309 0.5632 0.058 Uiso 1 1 calc R . . H3B H 0.3277 0.8974 0.5064 0.058 Uiso 1 1 calc R . . O1 O 0.5338(2) 0.1684(3) 0.58189(17) 0.0513(7) Uani 1 1 d . . . O2 O 0.4718(2) 0.3816(3) 0.58574(18) 0.0521(7) Uani 1 1 d . . . O3 O 0.2051(2) 0.0446(3) 0.11353(17) 0.0488(7) Uani 1 1 d . . . O4 O 0.2031(2) 0.2716(3) 0.07669(18) 0.0539(7) Uani 1 1 d . . . O5 O 0.7894(4) 0.2461(5) 0.6122(3) 0.0894(12) Uani 1 1 d D . . O6 O 0.8090(3) 0.2091(4) 0.8060(2) 0.0685(9) Uani 1 1 d D . . O7 O 0.5252(2) 0.2246(4) 0.8983(2) 0.0729(9) Uani 1 1 d D . . O8 O 0.6192(3) 0.3396(4) 0.7828(2) 0.0623(8) Uani 1 1 d D . . H5OB H 0.853(5) 0.192(10) 0.637(8) 0.25(6) Uiso 1 1 d D . . H5OA H 0.731(2) 0.288(4) 0.618(3) 0.043(11) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0429(18) 0.0400(19) 0.0293(18) -0.0083(16) 0.0147(15) -0.0073(16) C2 0.0346(16) 0.0395(19) 0.0284(17) -0.0052(15) 0.0146(14) -0.0052(15) C3 0.0440(19) 0.0361(18) 0.0377(19) -0.0051(16) 0.0201(16) -0.0007(16) C4 0.0339(17) 0.045(2) 0.0347(19) 0.0052(16) 0.0127(15) 0.0009(16) C5 0.0294(15) 0.045(2) 0.0256(17) -0.0005(15) 0.0106(13) -0.0048(15) C6 0.0370(17) 0.0383(18) 0.0259(17) -0.0039(14) 0.0109(14) -0.0044(15) C7 0.0313(16) 0.054(2) 0.0247(17) 0.0010(17) 0.0092(14) -0.0036(16) C8 0.050(2) 0.060(2) 0.040(2) 0.0129(19) 0.0226(17) 0.0117(19) C9 0.0391(18) 0.051(2) 0.0330(18) 0.0043(17) 0.0199(15) 0.0075(17) C10 0.0438(19) 0.0390(19) 0.041(2) 0.0025(16) 0.0199(16) 0.0044(16) C11 0.0418(19) 0.047(2) 0.0313(18) -0.0053(16) 0.0131(15) 0.0024(17) C12 0.0369(17) 0.043(2) 0.0321(18) 0.0035(16) 0.0145(15) 0.0031(16) C13 0.048(2) 0.040(2) 0.042(2) -0.0010(17) 0.0188(17) 0.0002(17) C14 0.0413(19) 0.056(2) 0.0295(18) -0.0065(17) 0.0119(15) 0.0029(18) Cu1 0.0585(4) 0.0395(4) 0.0232(4) -0.0050(3) -0.0025(3) 0.0060(3) N1 0.0368(14) 0.0388(16) 0.0239(14) -0.0030(12) 0.0080(12) -0.0025(12) N2 0.0431(16) 0.0431(16) 0.0272(15) 0.0043(13) 0.0105(12) -0.0009(14) N3 0.0570(19) 0.0484(18) 0.0325(16) 0.0094(15) 0.0135(14) 0.0007(16) O1 0.0605(16) 0.0458(15) 0.0269(13) -0.0075(12) 0.0004(12) 0.0045(13) O2 0.0663(17) 0.0488(15) 0.0338(14) -0.0123(12) 0.0154(12) 0.0015(13) O3 0.0561(16) 0.0535(16) 0.0257(13) -0.0060(12) 0.0082(11) -0.0066(13) O4 0.0505(15) 0.0675(18) 0.0290(13) 0.0102(13) 0.0042(11) -0.0116(14) O5 0.095(3) 0.104(3) 0.062(2) 0.001(2) 0.029(2) -0.022(3) O6 0.0698(19) 0.070(2) 0.0585(19) 0.0114(17) 0.0217(16) -0.0002(17) O7 0.0521(17) 0.098(3) 0.0529(19) -0.0076(19) 0.0088(15) -0.0036(18) O8 0.073(2) 0.071(2) 0.0351(16) -0.0070(15) 0.0173(15) 0.0105(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.227(4) . ? C1 O1 1.270(4) . ? C1 C2 1.513(4) . ? C2 N1 1.348(4) . ? C2 C3 1.366(5) . ? C3 C4 1.387(5) . ? C3 H3 0.9300 . ? C4 C5 1.377(5) . ? C4 H4 0.9300 . ? C5 C6 1.385(5) . ? C5 C7 1.516(4) . ? C6 N1 1.336(4) . ? C6 H6 0.9300 . ? C7 O3 1.246(4) . ? C7 O4 1.257(4) . ? C8 N2 1.483(4) . ? C8 C9 1.498(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.386(5) . ? C9 C14 1.390(5) . ? C10 C11 1.379(5) . ? C10 H10 0.9300 . ? C11 C12 1.392(5) . ? C11 H11 0.9300 . ? C12 C13 1.382(5) . ? C12 N3 1.404(4) . ? C13 C14 1.383(5) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? Cu1 N1 1.958(3) . ? Cu1 N1 1.958(3) 3_656 ? Cu1 O1 1.958(2) 3_656 ? Cu1 O1 1.958(2) . ? N2 H2A 0.8900 . ? N2 H2B 0.8900 . ? N2 H2C 0.8900 . ? N3 H3A 0.8600 . ? N3 H3B 0.8600 . ? O5 H5OB 0.958(12) . ? O5 H5OA 0.947(11) . ? O6 H6OA 0.96(2) . ? O6 H6OB 0.96(2) . ? O7 H7OA 0.93(2) . ? O7 H7OB 0.94(2) . ? O8 H8OA 0.94(2) . ? O8 H8OB 0.94(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 O2 C1 O1 124.7(3) . . ? O2 C1 C2 120.0(3) . . ? O1 C1 C2 115.3(3) . . ? N1 C2 C3 122.0(3) . . ? N1 C2 C1 113.1(3) . . ? C3 C2 C1 124.8(3) . . ? C2 C3 C4 118.7(3) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 119.9(3) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 118.2(3) . . ? C4 C5 C7 122.5(3) . . ? C6 C5 C7 119.3(3) . . ? N1 C6 C5 122.1(3) . . ? N1 C6 H6 118.9 . . ? C5 C6 H6 118.9 . . ? O3 C7 O4 125.2(3) . . ? O3 C7 C5 117.6(3) . . ? O4 C7 C5 117.1(3) . . ? N2 C8 C9 112.8(3) . . ? N2 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N2 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C14 117.3(3) . . ? C10 C9 C8 121.5(3) . . ? C14 C9 C8 121.1(3) . . ? C11 C10 C9 121.8(3) . . ? C11 C10 H10 119.1 . . ? C9 C10 H10 119.1 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11 119.9 . . ? C12 C11 H11 119.9 . . ? C13 C12 C11 118.8(3) . . ? C13 C12 N3 120.8(3) . . ? C11 C12 N3 120.4(3) . . ? C12 C13 C14 120.4(4) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C9 121.5(3) . . ? C13 C14 H14 119.2 . . ? C9 C14 H14 119.2 . . ? N1 Cu1 N1 180.00(15) . 3_656 ? N1 Cu1 O1 96.88(10) . 3_656 ? N1 Cu1 O1 83.12(10) 3_656 3_656 ? N1 Cu1 O1 83.12(10) . . ? N1 Cu1 O1 96.88(10) 3_656 . ? O1 Cu1 O1 180.00(13) 3_656 . ? C6 N1 C2 119.1(3) . . ? C6 N1 Cu1 127.4(2) . . ? C2 N1 Cu1 112.9(2) . . ? C8 N2 H2A 109.5 . . ? C8 N2 H2B 109.5 . . ? H2A N2 H2B 109.5 . . ? C8 N2 H2C 109.5 . . ? H2A N2 H2C 109.5 . . ? H2B N2 H2C 109.5 . . ? C12 N3 H3A 120.0 . . ? C12 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C1 O1 Cu1 114.5(2) . . ? H5OB O5 H5OA 153(7) . . ? H6OA O6 H6OB 118(8) . . ? H7OA O7 H7OB 103(5) . . ? H8OA O8 H8OB 122(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 N1 -168.5(3) . . . . ? O1 C1 C2 N1 10.9(4) . . . . ? O2 C1 C2 C3 14.3(5) . . . . ? O1 C1 C2 C3 -166.2(3) . . . . ? N1 C2 C3 C4 -0.9(5) . . . . ? C1 C2 C3 C4 176.0(3) . . . . ? C2 C3 C4 C5 2.0(5) . . . . ? C3 C4 C5 C6 -1.5(5) . . . . ? C3 C4 C5 C7 -179.1(3) . . . . ? C4 C5 C6 N1 0.0(5) . . . . ? C7 C5 C6 N1 177.6(3) . . . . ? C4 C5 C7 O3 -163.0(3) . . . . ? C6 C5 C7 O3 19.5(4) . . . . ? C4 C5 C7 O4 17.2(5) . . . . ? C6 C5 C7 O4 -160.3(3) . . . . ? N2 C8 C9 C10 70.5(4) . . . . ? N2 C8 C9 C14 -110.2(4) . . . . ? C14 C9 C10 C11 0.4(5) . . . . ? C8 C9 C10 C11 179.7(3) . . . . ? C9 C10 C11 C12 -1.0(5) . . . . ? C10 C11 C12 C13 1.0(5) . . . . ? C10 C11 C12 N3 178.4(3) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? N3 C12 C13 C14 -177.9(3) . . . . ? C12 C13 C14 C9 -0.1(5) . . . . ? C10 C9 C14 C13 0.2(5) . . . . ? C8 C9 C14 C13 -179.1(3) . . . . ? C5 C6 N1 C2 1.1(5) . . . . ? C5 C6 N1 Cu1 -170.1(2) . . . . ? C3 C2 N1 C6 -0.6(5) . . . . ? C1 C2 N1 C6 -177.8(3) . . . . ? C3 C2 N1 Cu1 171.8(2) . . . . ? C1 C2 N1 Cu1 -5.5(3) . . . . ? N1 Cu1 N1 C6 -146(100) 3_656 . . . ? O1 Cu1 N1 C6 -8.2(3) 3_656 . . . ? O1 Cu1 N1 C6 171.8(3) . . . . ? N1 Cu1 N1 C2 43(100) 3_656 . . . ? O1 Cu1 N1 C2 -179.8(2) 3_656 . . . ? O1 Cu1 N1 C2 0.2(2) . . . . ? O2 C1 O1 Cu1 168.7(3) . . . . ? C2 C1 O1 Cu1 -10.8(4) . . . . ? N1 Cu1 O1 C1 6.2(3) . . . . ? N1 Cu1 O1 C1 -173.8(3) 3_656 . . . ? O1 Cu1 O1 C1 -91(100) 3_656 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.609 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.061 _database_code_depnum_ccdc_archive 'CCDC 942365' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_25pdccuaq _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H24 Cu N6 O12' _chemical_formula_weight 748.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.6726(4) _cell_length_b 10.7950(10) _cell_length_c 12.0764(10) _cell_angle_alpha 65.544(9) _cell_angle_beta 79.053(6) _cell_angle_gamma 77.697(6) _cell_volume 768.56(11) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour red _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 383 _exptl_absorpt_coefficient_mu 0.790 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 4952 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0666 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.15 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2699 _reflns_number_gt 2175 _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^)+(0.1356P)^2^+1.1637P] 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 2699 _refine_ls_number_parameters 244 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0780 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1964 _refine_ls_wR_factor_gt 0.1779 _refine_ls_goodness_of_fit_ref 0.922 _refine_ls_restrained_S_all 0.922 _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 C1 C 0.5486(7) 0.4955(4) 0.2703(4) 0.0255(9) Uani 1 1 d . . . C2 C 0.7522(7) 0.4264(5) 0.3195(4) 0.0269(10) Uani 1 1 d . . . C3 C 0.9201(7) 0.3782(6) 0.2550(4) 0.0344(11) Uani 1 1 d . . . H3 H 0.9110 0.3841 0.1770 0.041 Uiso 1 1 calc R . . C4 C 1.1033(7) 0.3206(5) 0.3074(4) 0.0326(11) Uani 1 1 d . . . H4 H 1.2177 0.2868 0.2650 0.039 Uiso 1 1 calc R . . C5 C 1.1149(6) 0.3136(4) 0.4232(4) 0.0249(9) Uani 1 1 d . . . C6 C 0.9392(7) 0.3646(5) 0.4831(4) 0.0257(9) Uani 1 1 d . . . H6 H 0.9448 0.3605 0.5609 0.031 Uiso 1 1 calc R . . C7 C 1.3115(7) 0.2518(5) 0.4842(4) 0.0267(10) Uani 1 1 d . . . C8 C 0.6310(8) 0.0822(7) 0.2170(5) 0.0439(14) Uani 1 1 d . . . H8 H 0.5961 0.0898 0.2925 0.053 Uiso 1 1 calc R . . C9 C 0.6303(7) 0.2002(6) 0.1112(5) 0.0412(13) Uani 1 1 d . . . H9 H 0.5986 0.2867 0.1150 0.049 Uiso 1 1 calc R . . C10 C 0.6774(7) 0.1874(5) -0.0002(5) 0.0359(11) Uani 1 1 d . . . H10 H 0.6748 0.2659 -0.0723 0.043 Uiso 1 1 calc R . . C11 C 0.7296(6) 0.0565(5) -0.0058(4) 0.0267(10) Uani 1 1 d . . . C12 C 0.7793(7) 0.0350(5) -0.1182(4) 0.0311(10) Uani 1 1 d . . . C13 C 0.8311(7) -0.0988(5) -0.1111(4) 0.0330(11) Uani 1 1 d . . . H13 H 0.8640 -0.1142 -0.1832 0.040 Uiso 1 1 calc R . . C14 C 0.8356(7) -0.2112(6) 0.0005(5) 0.0367(11) Uani 1 1 d . . . H14 H 0.8734 -0.2994 0.0009 0.044 Uiso 1 1 calc R . . C15 C 0.7861(7) -0.1958(5) 0.1093(4) 0.0341(11) Uani 1 1 d . . . H15 H 0.7877 -0.2715 0.1835 0.041 Uiso 1 1 calc R . . C16 C 0.7325(6) -0.0606(5) 0.1048(4) 0.0288(10) Uani 1 1 d . . . Cu1 Cu 0.5000 0.5000 0.5000 0.0307(3) Uani 1 2 d S . . H3A H 0.808(10) 0.132(7) -0.306(6) 0.07(2) Uiso 1 1 d . . . H3B H 0.699(11) 0.229(8) -0.232(6) 0.08(2) Uiso 1 1 d . . . H2N H 0.681(11) -0.126(4) 0.281(4) 0.07(2) Uiso 1 1 d D . . N1 N 0.7619(5) 0.4195(4) 0.4325(3) 0.0248(8) Uani 1 1 d . . . N2 N 0.6800(6) -0.0407(5) 0.2132(4) 0.0340(9) Uani 1 1 d D . . N3 N 0.7773(7) 0.1442(5) -0.2298(4) 0.0420(11) Uani 1 1 d . . . O1 O 0.4175(5) 0.5466(3) 0.3389(3) 0.0310(7) Uani 1 1 d . . . O2 O 0.5214(5) 0.5026(4) 0.1705(3) 0.0385(9) Uani 1 1 d . . . O3 O 1.3204(5) 0.2729(4) 0.5780(3) 0.0354(8) Uani 1 1 d . . . O4 O 1.4487(6) 0.1873(5) 0.4362(4) 0.0568(12) Uani 1 1 d . . . O5 O 0.7952(6) 0.0468(5) 0.5623(4) 0.0588(11) Uani 1 1 d . . . O6 O 0.7751(16) 0.5026(12) 0.9658(10) 0.180(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.032(2) 0.018(2) 0.026(2) -0.0074(18) -0.0052(18) -0.0043(17) C2 0.030(2) 0.027(2) 0.027(2) -0.0130(19) -0.0036(18) -0.0047(18) C3 0.032(2) 0.051(3) 0.025(2) -0.021(2) -0.0038(18) -0.002(2) C4 0.027(2) 0.041(3) 0.031(2) -0.020(2) 0.0027(18) 0.000(2) C5 0.028(2) 0.020(2) 0.025(2) -0.0082(18) -0.0004(17) -0.0063(17) C6 0.030(2) 0.027(2) 0.022(2) -0.0104(19) -0.0027(17) -0.0090(18) C7 0.030(2) 0.023(2) 0.023(2) -0.0050(18) -0.0041(17) -0.0042(18) C8 0.035(3) 0.066(4) 0.044(3) -0.036(3) -0.007(2) -0.002(3) C9 0.032(3) 0.047(3) 0.054(3) -0.032(3) -0.005(2) 0.001(2) C10 0.023(2) 0.034(3) 0.045(3) -0.011(2) -0.0042(19) -0.0029(19) C11 0.015(2) 0.035(3) 0.032(2) -0.014(2) -0.0025(16) -0.0039(17) C12 0.022(2) 0.037(3) 0.034(2) -0.012(2) -0.0045(18) -0.0053(19) C13 0.026(2) 0.044(3) 0.033(2) -0.021(2) -0.0009(18) -0.004(2) C14 0.027(2) 0.038(3) 0.050(3) -0.023(2) -0.003(2) -0.004(2) C15 0.037(3) 0.030(3) 0.032(3) -0.007(2) -0.005(2) -0.006(2) C16 0.019(2) 0.040(3) 0.029(2) -0.016(2) -0.0036(17) -0.0030(18) Cu1 0.0255(5) 0.0404(6) 0.0271(5) -0.0179(4) -0.0055(3) 0.0056(3) N1 0.0252(18) 0.025(2) 0.0251(18) -0.0112(16) -0.0031(14) -0.0030(15) N2 0.030(2) 0.044(3) 0.029(2) -0.015(2) -0.0048(16) -0.0045(18) N3 0.048(3) 0.043(3) 0.027(2) -0.007(2) -0.0043(18) -0.004(2) O1 0.0269(16) 0.0374(19) 0.0303(16) -0.0176(15) -0.0070(13) 0.0043(14) O2 0.0401(19) 0.045(2) 0.0305(18) -0.0168(16) -0.0118(14) 0.0044(16) O3 0.0350(18) 0.043(2) 0.0280(17) -0.0138(15) -0.0095(13) -0.0001(15) O4 0.044(2) 0.079(3) 0.056(2) -0.046(2) -0.0231(18) 0.030(2) O5 0.050(2) 0.063(3) 0.054(2) -0.019(2) -0.0055(19) 0.001(2) O6 0.165(9) 0.192(11) 0.188(9) -0.073(8) -0.035(7) -0.029(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 C1 O2 1.222(5) . ? C1 O1 1.286(5) . ? C1 C2 1.504(6) . ? C2 N1 1.349(5) . ? C2 C3 1.374(6) . ? C3 C4 1.388(7) . ? C3 H3 0.9300 . ? C4 C5 1.386(6) . ? C4 H4 0.9300 . ? C5 C6 1.389(6) . ? C5 C7 1.515(6) . ? C6 N1 1.342(6) . ? C6 H6 0.9300 . ? C7 O4 1.233(6) . ? C7 O3 1.259(5) . ? C8 N2 1.315(7) . ? C8 C9 1.381(8) . ? C8 H8 0.9300 . ? C9 C10 1.379(7) . ? C9 H9 0.9300 . ? C10 C11 1.409(7) . ? C10 H10 0.9300 . ? C11 C16 1.408(6) . ? C11 C12 1.437(6) . ? C12 N3 1.375(6) . ? C12 C13 1.381(7) . ? C13 C14 1.392(7) . ? C13 H13 0.9300 . ? C14 C15 1.362(7) . ? C14 H14 0.9300 . ? C15 C16 1.406(7) . ? C15 H15 0.9300 . ? C16 N2 1.382(6) . ? Cu1 O1 1.955(3) 2_666 ? Cu1 O1 1.955(3) . ? Cu1 N1 1.968(3) 2_666 ? Cu1 N1 1.968(3) . ? N2 H2N 0.95(2) . ? N3 H3A 0.97(7) . ? N3 H3B 0.94(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.4(4) . . ? O2 C1 C2 119.7(4) . . ? O1 C1 C2 114.9(4) . . ? N1 C2 C3 121.4(4) . . ? N1 C2 C1 114.5(4) . . ? C3 C2 C1 124.0(4) . . ? C2 C3 C4 119.3(4) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 117.9(4) . . ? C4 C5 C7 121.6(4) . . ? C6 C5 C7 120.5(4) . . ? N1 C6 C5 122.3(4) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? O4 C7 O3 126.2(4) . . ? O4 C7 C5 116.9(4) . . ? O3 C7 C5 116.9(4) . . ? N2 C8 C9 121.3(5) . . ? N2 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C10 C9 C8 118.7(5) . . ? C10 C9 H9 120.6 . . ? C8 C9 H9 120.6 . . ? C9 C10 C11 120.6(5) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C16 C11 C10 118.5(4) . . ? C16 C11 C12 117.7(4) . . ? C10 C11 C12 123.8(4) . . ? N3 C12 C13 120.8(4) . . ? N3 C12 C11 121.1(5) . . ? C13 C12 C11 118.1(4) . . ? C12 C13 C14 122.0(4) . . ? C12 C13 H13 119.0 . . ? C14 C13 H13 119.0 . . ? C15 C14 C13 121.9(5) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 117.3(4) . . ? C14 C15 H15 121.4 . . ? C16 C15 H15 121.4 . . ? N2 C16 C15 119.0(4) . . ? N2 C16 C11 118.0(4) . . ? C15 C16 C11 123.0(4) . . ? O1 Cu1 O1 180.000(1) 2_666 . ? O1 Cu1 N1 83.33(13) 2_666 2_666 ? O1 Cu1 N1 96.67(13) . 2_666 ? O1 Cu1 N1 96.67(13) 2_666 . ? O1 Cu1 N1 83.33(13) . . ? N1 Cu1 N1 180.000(1) 2_666 . ? C6 N1 C2 119.4(4) . . ? C6 N1 Cu1 128.5(3) . . ? C2 N1 Cu1 112.1(3) . . ? C8 N2 C16 122.9(4) . . ? C8 N2 H2N 126(4) . . ? C16 N2 H2N 111(4) . . ? C12 N3 H3A 122(4) . . ? C12 N3 H3B 118(4) . . ? H3A N3 H3B 117(6) . . ? C1 O1 Cu1 114.6(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 N1 -177.4(4) . . . . ? O1 C1 C2 N1 4.6(6) . . . . ? O2 C1 C2 C3 5.1(7) . . . . ? O1 C1 C2 C3 -172.9(4) . . . . ? N1 C2 C3 C4 0.3(8) . . . . ? C1 C2 C3 C4 177.6(4) . . . . ? C2 C3 C4 C5 -0.6(8) . . . . ? C3 C4 C5 C6 0.5(7) . . . . ? C3 C4 C5 C7 -179.9(4) . . . . ? C4 C5 C6 N1 -0.1(7) . . . . ? C7 C5 C6 N1 -179.7(4) . . . . ? C4 C5 C7 O4 -12.0(7) . . . . ? C6 C5 C7 O4 167.6(5) . . . . ? C4 C5 C7 O3 167.0(4) . . . . ? C6 C5 C7 O3 -13.4(6) . . . . ? N2 C8 C9 C10 1.5(8) . . . . ? C8 C9 C10 C11 -1.3(7) . . . . ? C9 C10 C11 C16 0.0(6) . . . . ? C9 C10 C11 C12 179.6(4) . . . . ? C16 C11 C12 N3 179.2(4) . . . . ? C10 C11 C12 N3 -0.4(7) . . . . ? C16 C11 C12 C13 -1.4(6) . . . . ? C10 C11 C12 C13 179.0(4) . . . . ? N3 C12 C13 C14 179.6(4) . . . . ? C11 C12 C13 C14 0.2(6) . . . . ? C12 C13 C14 C15 1.0(7) . . . . ? C13 C14 C15 C16 -0.9(7) . . . . ? C14 C15 C16 N2 179.6(4) . . . . ? C14 C15 C16 C11 -0.4(7) . . . . ? C10 C11 C16 N2 1.2(6) . . . . ? C12 C11 C16 N2 -178.4(4) . . . . ? C10 C11 C16 C15 -178.8(4) . . . . ? C12 C11 C16 C15 1.5(6) . . . . ? C5 C6 N1 C2 -0.2(6) . . . . ? C5 C6 N1 Cu1 -178.6(3) . . . . ? C3 C2 N1 C6 0.1(7) . . . . ? C1 C2 N1 C6 -177.5(4) . . . . ? C3 C2 N1 Cu1 178.8(4) . . . . ? C1 C2 N1 Cu1 1.2(5) . . . . ? O1 Cu1 N1 C6 -5.7(4) 2_666 . . . ? O1 Cu1 N1 C6 174.3(4) . . . . ? N1 Cu1 N1 C6 -152(100) 2_666 . . . ? O1 Cu1 N1 C2 175.8(3) 2_666 . . . ? O1 Cu1 N1 C2 -4.2(3) . . . . ? N1 Cu1 N1 C2 30(100) 2_666 . . . ? C9 C8 N2 C16 -0.3(7) . . . . ? C15 C16 N2 C8 179.0(4) . . . . ? C11 C16 N2 C8 -1.1(6) . . . . ? O2 C1 O1 Cu1 174.0(4) . . . . ? C2 C1 O1 Cu1 -8.1(5) . . . . ? O1 Cu1 O1 C1 -104(100) 2_666 . . . ? N1 Cu1 O1 C1 -172.9(3) 2_666 . . . ? N1 Cu1 O1 C1 7.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.703 _refine_diff_density_min -0.835 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 942366' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_25pdccudabco1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H32 Cu N4 O14' _chemical_formula_weight 616.04 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 9.0129(15) _cell_length_b 12.6761(17) _cell_length_c 13.0543(12) _cell_angle_alpha 113.147(11) _cell_angle_beta 90.103(11) _cell_angle_gamma 105.573(13) _cell_volume 1311.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 642 _exptl_absorpt_coefficient_mu 0.910 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 8200 _diffrn_reflns_av_R_equivalents 0.0469 _diffrn_reflns_av_sigmaI/netI 0.0809 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4592 _reflns_number_gt 3259 _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^)+(0.1034P)^2^+0.0200P] 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 4592 _refine_ls_number_parameters 408 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1014 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.2020 _refine_ls_wR_factor_gt 0.1635 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu0A Cu 0.62281(7) 0.76305(6) 0.98750(5) 0.0405(3) Uani 1 1 d . . . O5 O 0.5659(4) 0.6863(3) 0.8260(3) 0.0423(9) Uani 1 1 d . . . O1 O 0.6869(4) 0.8588(3) 1.1466(3) 0.0472(9) Uani 1 1 d . . . N2 N 0.4526(5) 0.8325(3) 0.9828(3) 0.0331(9) Uani 1 1 d . . . O3 O 1.0211(5) 0.5129(4) 0.7397(3) 0.0715(13) Uani 1 1 d . . . O6 O 0.4005(4) 0.6685(3) 0.6902(3) 0.0490(10) Uani 1 1 d . . . N1 N 0.8142(5) 0.7175(4) 0.9956(3) 0.0371(10) Uani 1 1 d . . . O4 O 1.2021(5) 0.5222(4) 0.8577(3) 0.0620(11) Uani 1 1 d . . . O2 O 0.8556(4) 0.8876(3) 1.2877(3) 0.0517(10) Uani 1 1 d . . . O7 O 0.3062(5) 1.0652(3) 1.2506(3) 0.0554(11) Uani 1 1 d . . . O9 O 0.4563(5) 0.6006(4) 1.0142(3) 0.0512(10) Uani 1 1 d D . . O8 O 0.1211(5) 1.0726(4) 1.1455(3) 0.0769(15) Uani 1 1 d . . . O10 O 0.2760(6) 0.5793(5) 0.3629(4) 0.0674(12) Uani 1 1 d . . . O11 O 0.2445(6) 0.7451(5) 0.5680(4) 0.0770(15) Uani 1 1 d D . . N3 N 0.7606(5) 0.7749(4) 0.5779(3) 0.0414(10) Uani 1 1 d D . . O12 O 0.5921(9) 0.3043(6) 0.7637(5) 0.112(2) Uani 1 1 d D . . O14 O 0.6841(10) 1.0265(6) 0.4245(5) 0.1042(19) Uani 1 1 d D . . C2 C 0.8840(6) 0.7638(4) 1.1020(4) 0.0365(11) Uani 1 1 d . . . N4 N 0.8267(6) 0.6273(4) 0.4070(4) 0.0528(13) Uani 1 1 d . . . C12 C 0.2796(6) 0.9502(4) 1.0576(4) 0.0354(11) Uani 1 1 d . . . C6 C 0.8771(6) 0.6472(4) 0.9128(4) 0.0389(12) Uani 1 1 d . . . H6 H 0.8295 0.6156 0.8395 0.047 Uiso 1 1 calc R . . C9 C 0.3811(6) 0.7949(4) 0.8793(4) 0.0328(11) Uani 1 1 d . . . C5 C 1.0116(6) 0.6196(4) 0.9325(4) 0.0395(12) Uani 1 1 d . . . C1 C 0.8038(6) 0.8433(4) 1.1871(4) 0.0376(12) Uani 1 1 d . . . C14 C 0.2279(6) 1.0355(4) 1.1567(4) 0.0413(12) Uani 1 1 d . . . O13 O 0.6581(11) 0.0890(6) 0.6512(5) 0.121(2) Uani 1 1 d D . . C13 C 0.4032(6) 0.9081(4) 1.0692(4) 0.0353(11) Uani 1 1 d . . . H13 H 0.4537 0.9340 1.1407 0.042 Uiso 1 1 calc R . . C8 C 0.4544(6) 0.7096(4) 0.7897(4) 0.0351(11) Uani 1 1 d . . . C10 C 0.2583(6) 0.8310(4) 0.8590(4) 0.0371(12) Uani 1 1 d . . . H10 H 0.2111 0.8035 0.7862 0.045 Uiso 1 1 calc R . . C16 C 0.8374(8) 0.5916(5) 0.5022(5) 0.0574(16) Uani 1 1 d . . . H16A H 0.9426 0.5915 0.5176 0.069 Uiso 1 1 calc R . . H16B H 0.7688 0.5113 0.4829 0.069 Uiso 1 1 calc R . . C3 C 1.0158(6) 0.7388(5) 1.1279(4) 0.0400(12) Uani 1 1 d . . . H3 H 1.0602 0.7700 1.2019 0.048 Uiso 1 1 calc R . . C4 C 1.0797(6) 0.6680(5) 1.0435(4) 0.0426(13) Uani 1 1 d . . . H4 H 1.1693 0.6517 1.0599 0.051 Uiso 1 1 calc R . . C15 C 0.7913(8) 0.6802(5) 0.6050(5) 0.0600(17) Uani 1 1 d . . . H15A H 0.6990 0.6392 0.6279 0.072 Uiso 1 1 calc R . . H15B H 0.8742 0.7151 0.6666 0.072 Uiso 1 1 calc R . . C11 C 0.2049(6) 0.9096(4) 0.9488(4) 0.0397(12) Uani 1 1 d . . . H11 H 0.1211 0.9348 0.9368 0.048 Uiso 1 1 calc R . . C20 C 0.9367(7) 0.7481(5) 0.4345(5) 0.0575(16) Uani 1 1 d . . . H20A H 0.9280 0.7720 0.3732 0.069 Uiso 1 1 calc R . . H20B H 1.0423 0.7462 0.4452 0.069 Uiso 1 1 calc R . . C7 C 1.0843(6) 0.5455(5) 0.8361(5) 0.0504(14) Uani 1 1 d . . . C19 C 0.8992(8) 0.8367(6) 0.5401(5) 0.0641(17) Uani 1 1 d . . . H19A H 0.9867 0.8708 0.5981 0.077 Uiso 1 1 calc R . . H19B H 0.8790 0.9015 0.5258 0.077 Uiso 1 1 calc R . . C18 C 0.6284(8) 0.7225(6) 0.4891(5) 0.0654(18) Uani 1 1 d . . . H18A H 0.6070 0.7852 0.4719 0.078 Uiso 1 1 calc R . . H18B H 0.5366 0.6844 0.5145 0.078 Uiso 1 1 calc R . . C17 C 0.6673(7) 0.6303(6) 0.3844(5) 0.0603(17) Uani 1 1 d . . . H17A H 0.5942 0.5518 0.3657 0.072 Uiso 1 1 calc R . . H17B H 0.6604 0.6520 0.3215 0.072 Uiso 1 1 calc R . . H4N H 0.856(7) 0.566(5) 0.342(5) 0.068(18) Uiso 1 1 d . . . H3N H 0.742(8) 0.841(4) 0.640(4) 0.10(2) Uiso 1 1 d D . . H9OB H 0.365(4) 0.567(5) 0.963(4) 0.064(19) Uiso 1 1 d D . . H12C H 0.637(16) 0.352(10) 0.724(10) 0.27(7) Uiso 1 1 d D . . H12D H 0.605(5) 0.225(2) 0.733(3) 0.030(13) Uiso 1 1 d D . . H10D H 0.284(9) 0.653(7) 0.433(7) 0.10(3) Uiso 1 1 d . . . H10C H 0.175(11) 0.549(8) 0.332(7) 0.13(4) Uiso 1 1 d . . . H11C H 0.307(8) 0.725(6) 0.612(5) 0.11(3) Uiso 1 1 d D . . H13C H 0.719(13) 0.073(12) 0.589(7) 0.22(6) Uiso 1 1 d D . . H13D H 0.706(16) 0.052(11) 0.688(10) 0.24(6) Uiso 1 1 d D . . H11D H 0.291(10) 0.825(4) 0.574(8) 0.15(4) Uiso 1 1 d D . . H14C H 0.757(14) 0.991(13) 0.382(10) 0.26(7) Uiso 1 1 d D . . H14D H 0.598(9) 0.956(7) 0.394(10) 0.20(6) Uiso 1 1 d D . . H9OA H 0.416(10) 0.609(8) 1.084(4) 0.16(4) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu0A 0.0355(4) 0.0607(5) 0.0316(4) 0.0163(3) 0.0131(3) 0.0277(3) O5 0.0303(19) 0.070(2) 0.0334(18) 0.0183(17) 0.0119(15) 0.0295(18) O1 0.035(2) 0.073(2) 0.0363(19) 0.0156(18) 0.0092(17) 0.029(2) N2 0.029(2) 0.046(2) 0.029(2) 0.0159(18) 0.0114(18) 0.018(2) O3 0.056(3) 0.097(3) 0.039(2) -0.003(2) 0.013(2) 0.035(3) O6 0.047(2) 0.070(2) 0.0306(19) 0.0142(18) 0.0134(17) 0.029(2) N1 0.035(2) 0.049(2) 0.030(2) 0.0150(19) 0.0144(18) 0.020(2) O4 0.043(2) 0.073(3) 0.072(3) 0.023(2) 0.026(2) 0.032(2) O2 0.049(2) 0.077(3) 0.0309(19) 0.0122(18) 0.0109(17) 0.036(2) O7 0.067(3) 0.073(3) 0.035(2) 0.0148(19) 0.014(2) 0.046(2) O9 0.047(3) 0.065(3) 0.051(2) 0.028(2) 0.020(2) 0.026(2) O8 0.065(3) 0.100(3) 0.056(3) -0.002(2) -0.002(2) 0.061(3) O10 0.057(3) 0.085(3) 0.054(3) 0.021(3) 0.013(2) 0.022(3) O11 0.082(4) 0.107(4) 0.054(3) 0.028(3) 0.004(3) 0.055(3) N3 0.040(3) 0.050(3) 0.037(2) 0.016(2) 0.016(2) 0.020(2) O12 0.156(6) 0.114(5) 0.092(4) 0.057(4) 0.060(4) 0.059(5) O14 0.125(6) 0.111(5) 0.089(4) 0.035(4) 0.062(4) 0.063(5) C2 0.035(3) 0.046(3) 0.032(3) 0.019(2) 0.014(2) 0.013(2) N4 0.062(3) 0.065(3) 0.039(3) 0.015(2) 0.022(2) 0.038(3) C12 0.026(3) 0.051(3) 0.035(3) 0.019(2) 0.013(2) 0.017(2) C6 0.037(3) 0.046(3) 0.030(3) 0.012(2) 0.016(2) 0.014(3) C9 0.029(3) 0.044(3) 0.033(2) 0.022(2) 0.013(2) 0.012(2) C5 0.035(3) 0.043(3) 0.044(3) 0.019(2) 0.020(2) 0.014(2) C1 0.034(3) 0.051(3) 0.034(3) 0.018(2) 0.013(2) 0.021(3) C14 0.039(3) 0.043(3) 0.044(3) 0.014(2) 0.014(3) 0.022(3) O13 0.198(8) 0.136(5) 0.074(4) 0.056(4) 0.039(5) 0.097(6) C13 0.035(3) 0.046(3) 0.029(2) 0.016(2) 0.011(2) 0.018(2) C8 0.030(3) 0.045(3) 0.032(3) 0.015(2) 0.018(2) 0.014(2) C10 0.034(3) 0.050(3) 0.030(2) 0.015(2) 0.009(2) 0.018(2) C16 0.080(5) 0.060(4) 0.053(3) 0.032(3) 0.033(3) 0.039(4) C3 0.031(3) 0.058(3) 0.034(3) 0.020(2) 0.011(2) 0.017(3) C4 0.036(3) 0.062(3) 0.036(3) 0.016(3) 0.010(2) 0.030(3) C15 0.080(5) 0.072(4) 0.043(3) 0.025(3) 0.029(3) 0.046(4) C11 0.034(3) 0.051(3) 0.041(3) 0.022(2) 0.011(2) 0.020(3) C20 0.049(4) 0.079(4) 0.062(4) 0.037(3) 0.027(3) 0.034(4) C7 0.032(3) 0.050(3) 0.059(4) 0.010(3) 0.024(3) 0.015(3) C19 0.054(4) 0.061(4) 0.069(4) 0.022(3) 0.021(3) 0.011(3) C18 0.053(4) 0.081(4) 0.049(3) 0.004(3) 0.010(3) 0.034(4) C17 0.052(4) 0.080(4) 0.043(3) 0.013(3) 0.008(3) 0.031(4) _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 Cu0A O1 1.939(3) . ? Cu0A O5 1.942(3) . ? Cu0A N2 1.974(4) . ? Cu0A N1 1.975(4) . ? Cu0A O9 2.350(4) . ? O5 C8 1.261(5) . ? O1 C1 1.272(5) . ? N2 C13 1.330(6) . ? N2 C9 1.340(6) . ? O3 C7 1.241(7) . ? O6 C8 1.235(5) . ? N1 C6 1.343(6) . ? N1 C2 1.351(6) . ? O4 C7 1.235(6) . ? O2 C1 1.239(6) . ? O7 C14 1.279(6) . ? O9 H9OB 0.941(15) . ? O9 H9OA 0.952(15) . ? O8 C14 1.211(6) . ? O10 H10D 1.00(8) . ? O10 H10C 0.91(9) . ? O11 H11C 0.95(2) . ? O11 H11D 0.95(2) . ? N3 C15 1.467(6) . ? N3 C18 1.474(7) . ? N3 C19 1.483(8) . ? N3 H3N 0.96(2) . ? O12 H12C 0.961(15) . ? O12 H12D 0.961(19) . ? O14 H14C 0.95(2) . ? O14 H14D 0.95(2) . ? C2 C3 1.382(7) . ? C2 C1 1.512(7) . ? N4 C17 1.479(7) . ? N4 C20 1.486(8) . ? N4 C16 1.491(7) . ? N4 H4N 0.99(6) . ? C12 C13 1.389(6) . ? C12 C11 1.404(6) . ? C12 C14 1.494(7) . ? C6 C5 1.397(7) . ? C6 H6 0.9300 . ? C9 C10 1.368(6) . ? C9 C8 1.537(6) . ? C5 C4 1.396(7) . ? C5 C7 1.517(7) . ? O13 H13C 0.96(2) . ? O13 H13D 0.96(2) . ? C13 H13 0.9300 . ? C10 C11 1.392(7) . ? C10 H10 0.9300 . ? C16 C15 1.518(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C3 C4 1.362(7) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C11 H11 0.9300 . ? C20 C19 1.505(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C18 C17 1.524(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu0A O5 172.76(15) . . ? O1 Cu0A N2 93.97(14) . . ? O5 Cu0A N2 82.83(14) . . ? O1 Cu0A N1 83.13(15) . . ? O5 Cu0A N1 99.10(14) . . ? N2 Cu0A N1 171.36(16) . . ? O1 Cu0A O9 93.93(16) . . ? O5 Cu0A O9 92.70(15) . . ? N2 Cu0A O9 92.42(15) . . ? N1 Cu0A O9 95.90(15) . . ? C8 O5 Cu0A 115.8(3) . . ? C1 O1 Cu0A 115.4(3) . . ? C13 N2 C9 119.0(4) . . ? C13 N2 Cu0A 127.4(3) . . ? C9 N2 Cu0A 113.6(3) . . ? C6 N1 C2 118.7(4) . . ? C6 N1 Cu0A 129.2(3) . . ? C2 N1 Cu0A 112.1(3) . . ? Cu0A O9 H9OB 110(3) . . ? Cu0A O9 H9OA 122(6) . . ? H9OB O9 H9OA 102(7) . . ? H10D O10 H10C 108(7) . . ? H11C O11 H11D 111(7) . . ? C15 N3 C18 109.8(5) . . ? C15 N3 C19 110.7(5) . . ? C18 N3 C19 109.6(5) . . ? C15 N3 H3N 116(4) . . ? C18 N3 H3N 109(4) . . ? C19 N3 H3N 102(4) . . ? H12C O12 H12D 114(9) . . ? H14C O14 H14D 96(10) . . ? N1 C2 C3 122.0(5) . . ? N1 C2 C1 113.6(4) . . ? C3 C2 C1 124.5(4) . . ? C17 N4 C20 109.1(4) . . ? C17 N4 C16 110.3(5) . . ? C20 N4 C16 110.0(5) . . ? C17 N4 H4N 111(3) . . ? C20 N4 H4N 110(4) . . ? C16 N4 H4N 106(3) . . ? C13 C12 C11 117.3(4) . . ? C13 C12 C14 121.6(4) . . ? C11 C12 C14 121.1(4) . . ? N1 C6 C5 122.5(4) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? N2 C9 C10 122.3(4) . . ? N2 C9 C8 112.1(4) . . ? C10 C9 C8 125.6(4) . . ? C4 C5 C6 117.3(4) . . ? C4 C5 C7 121.7(5) . . ? C6 C5 C7 120.9(5) . . ? O2 C1 O1 125.8(4) . . ? O2 C1 C2 118.9(4) . . ? O1 C1 C2 115.2(4) . . ? O8 C14 O7 124.4(5) . . ? O8 C14 C12 121.0(5) . . ? O7 C14 C12 114.5(4) . . ? H13C O13 H13D 94(10) . . ? N2 C13 C12 123.2(4) . . ? N2 C13 H13 118.4 . . ? C12 C13 H13 118.4 . . ? O6 C8 O5 125.2(4) . . ? O6 C8 C9 119.0(4) . . ? O5 C8 C9 115.7(4) . . ? C9 C10 C11 119.2(4) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? N4 C16 C15 108.9(4) . . ? N4 C16 H16A 109.9 . . ? C15 C16 H16A 109.9 . . ? N4 C16 H16B 109.9 . . ? C15 C16 H16B 109.9 . . ? H16A C16 H16B 108.3 . . ? C4 C3 C2 119.1(4) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? N3 C15 C16 109.1(4) . . ? N3 C15 H15A 109.9 . . ? C16 C15 H15A 109.9 . . ? N3 C15 H15B 109.9 . . ? C16 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C10 C11 C12 119.0(4) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? N4 C20 C19 109.0(5) . . ? N4 C20 H20A 109.9 . . ? C19 C20 H20A 109.9 . . ? N4 C20 H20B 109.9 . . ? C19 C20 H20B 109.9 . . ? H20A C20 H20B 108.3 . . ? O4 C7 O3 124.2(5) . . ? O4 C7 C5 118.6(5) . . ? O3 C7 C5 117.1(5) . . ? N3 C19 C20 109.3(5) . . ? N3 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? N3 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.3 . . ? N3 C18 C17 109.2(5) . . ? N3 C18 H18A 109.8 . . ? C17 C18 H18A 109.8 . . ? N3 C18 H18B 109.8 . . ? C17 C18 H18B 109.8 . . ? H18A C18 H18B 108.3 . . ? N4 C17 C18 108.6(5) . . ? N4 C17 H17A 110.0 . . ? C18 C17 H17A 110.0 . . ? N4 C17 H17B 110.0 . . ? C18 C17 H17B 110.0 . . ? H17A C17 H17B 108.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu0A O5 C8 -64.8(12) . . . . ? N2 Cu0A O5 C8 -0.7(3) . . . . ? N1 Cu0A O5 C8 -172.2(3) . . . . ? O9 Cu0A O5 C8 91.4(3) . . . . ? O5 Cu0A O1 C1 -115.0(10) . . . . ? N2 Cu0A O1 C1 -178.5(4) . . . . ? N1 Cu0A O1 C1 -6.6(4) . . . . ? O9 Cu0A O1 C1 88.8(4) . . . . ? O1 Cu0A N2 C13 -6.3(4) . . . . ? O5 Cu0A N2 C13 -179.7(4) . . . . ? N1 Cu0A N2 C13 -76.3(11) . . . . ? O9 Cu0A N2 C13 87.9(4) . . . . ? O1 Cu0A N2 C9 174.9(3) . . . . ? O5 Cu0A N2 C9 1.4(3) . . . . ? N1 Cu0A N2 C9 104.9(10) . . . . ? O9 Cu0A N2 C9 -91.0(3) . . . . ? O1 Cu0A N1 C6 -177.0(5) . . . . ? O5 Cu0A N1 C6 -3.9(5) . . . . ? N2 Cu0A N1 C6 -106.2(10) . . . . ? O9 Cu0A N1 C6 89.7(4) . . . . ? O1 Cu0A N1 C2 5.0(3) . . . . ? O5 Cu0A N1 C2 178.0(3) . . . . ? N2 Cu0A N1 C2 75.8(10) . . . . ? O9 Cu0A N1 C2 -88.3(3) . . . . ? C6 N1 C2 C3 -1.3(7) . . . . ? Cu0A N1 C2 C3 177.0(4) . . . . ? C6 N1 C2 C1 178.8(4) . . . . ? Cu0A N1 C2 C1 -2.9(5) . . . . ? C2 N1 C6 C5 0.3(7) . . . . ? Cu0A N1 C6 C5 -177.6(4) . . . . ? C13 N2 C9 C10 -0.3(7) . . . . ? Cu0A N2 C9 C10 178.7(4) . . . . ? C13 N2 C9 C8 179.2(4) . . . . ? Cu0A N2 C9 C8 -1.8(5) . . . . ? N1 C6 C5 C4 0.3(7) . . . . ? N1 C6 C5 C7 -176.6(5) . . . . ? Cu0A O1 C1 O2 -173.7(4) . . . . ? Cu0A O1 C1 C2 6.7(6) . . . . ? N1 C2 C1 O2 178.0(5) . . . . ? C3 C2 C1 O2 -1.9(8) . . . . ? N1 C2 C1 O1 -2.4(7) . . . . ? C3 C2 C1 O1 177.7(5) . . . . ? C13 C12 C14 O8 179.2(5) . . . . ? C11 C12 C14 O8 -0.6(8) . . . . ? C13 C12 C14 O7 0.0(7) . . . . ? C11 C12 C14 O7 -179.9(5) . . . . ? C9 N2 C13 C12 0.3(7) . . . . ? Cu0A N2 C13 C12 -178.5(4) . . . . ? C11 C12 C13 N2 0.1(7) . . . . ? C14 C12 C13 N2 -179.7(5) . . . . ? Cu0A O5 C8 O6 -179.2(4) . . . . ? Cu0A O5 C8 C9 -0.1(5) . . . . ? N2 C9 C8 O6 -179.6(4) . . . . ? C10 C9 C8 O6 -0.1(7) . . . . ? N2 C9 C8 O5 1.3(6) . . . . ? C10 C9 C8 O5 -179.2(4) . . . . ? N2 C9 C10 C11 -0.1(7) . . . . ? C8 C9 C10 C11 -179.5(5) . . . . ? C17 N4 C16 C15 -58.3(7) . . . . ? C20 N4 C16 C15 62.0(7) . . . . ? N1 C2 C3 C4 1.7(8) . . . . ? C1 C2 C3 C4 -178.5(5) . . . . ? C2 C3 C4 C5 -1.0(8) . . . . ? C6 C5 C4 C3 0.1(8) . . . . ? C7 C5 C4 C3 176.9(5) . . . . ? C18 N3 C15 C16 63.0(7) . . . . ? C19 N3 C15 C16 -58.2(7) . . . . ? N4 C16 C15 N3 -3.3(8) . . . . ? C9 C10 C11 C12 0.5(7) . . . . ? C13 C12 C11 C10 -0.5(7) . . . . ? C14 C12 C11 C10 179.4(5) . . . . ? C17 N4 C20 C19 62.8(6) . . . . ? C16 N4 C20 C19 -58.3(6) . . . . ? C4 C5 C7 O4 4.1(8) . . . . ? C6 C5 C7 O4 -179.2(5) . . . . ? C4 C5 C7 O3 -175.3(5) . . . . ? C6 C5 C7 O3 1.4(8) . . . . ? C15 N3 C19 C20 62.2(6) . . . . ? C18 N3 C19 C20 -59.1(6) . . . . ? N4 C20 C19 N3 -2.7(7) . . . . ? C15 N3 C18 C17 -60.4(7) . . . . ? C19 N3 C18 C17 61.5(7) . . . . ? C20 N4 C17 C18 -60.1(6) . . . . ? C16 N4 C17 C18 60.8(7) . . . . ? N3 C18 C17 N4 -1.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.780 _refine_diff_density_min -0.800 _refine_diff_density_rms 0.094 _database_code_depnum_ccdc_archive 'CCDC 942367' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_kps2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H84 Cu3 N12 O40' _chemical_formula_weight 1876.07 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 '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 11.0057(4) _cell_length_b 14.0625(6) _cell_length_c 14.8817(6) _cell_angle_alpha 104.224(2) _cell_angle_beta 104.901(2) _cell_angle_gamma 95.615(2) _cell_volume 2125.40(15) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour 0.28 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.466 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 971 _exptl_absorpt_coefficient_mu 0.842 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 22258 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0409 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 24.50 _reflns_number_total 6879 _reflns_number_gt 5057 _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^)+(0.0546P)^2^+3.5412P] 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 6879 _refine_ls_number_parameters 550 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1162 _refine_ls_goodness_of_fit_ref 0.954 _refine_ls_restrained_S_all 0.954 _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 C1 C 0.7390(4) 0.2247(3) 0.1340(3) 0.0427(9) Uani 1 1 d . . . C2 C 0.8411(3) 0.1759(3) 0.1850(3) 0.0341(8) Uani 1 1 d . . . C3 C 0.8231(4) 0.0753(3) 0.1774(3) 0.0405(9) Uani 1 1 d . . . H3 H 0.7463 0.0340 0.1399 0.049 Uiso 1 1 calc R . . C4 C 0.9221(4) 0.0378(3) 0.2269(3) 0.0405(9) Uani 1 1 d . . . H4 H 0.9115 -0.0292 0.2247 0.049 Uiso 1 1 calc R . . C5 C 1.0370(3) 0.0993(3) 0.2796(3) 0.0348(8) Uani 1 1 d . . . C6 C 1.0480(3) 0.1998(3) 0.2829(3) 0.0334(8) Uani 1 1 d . . . H6 H 1.1251 0.2420 0.3177 0.040 Uiso 1 1 calc R . . C7 C 1.1479(4) 0.0593(3) 0.3330(3) 0.0434(10) Uani 1 1 d . . . C8 C 1.1374(3) 0.5255(3) 0.3393(3) 0.0358(9) Uani 1 1 d . . . C9 C 1.0384(3) 0.5782(3) 0.2896(3) 0.0330(8) Uani 1 1 d . . . C10 C 1.0620(3) 0.6779(3) 0.2942(3) 0.0361(9) Uani 1 1 d . . . H10 H 1.1414 0.7167 0.3290 0.043 Uiso 1 1 calc R . . C11 C 0.9648(3) 0.7188(3) 0.2457(3) 0.0365(9) Uani 1 1 d . . . H11 H 0.9786 0.7855 0.2472 0.044 Uiso 1 1 calc R . . C12 C 0.8472(3) 0.6597(3) 0.1951(3) 0.0342(8) Uani 1 1 d . . . C13 C 0.8306(3) 0.5598(3) 0.1940(3) 0.0343(8) Uani 1 1 d . . . H13 H 0.7517 0.5197 0.1604 0.041 Uiso 1 1 calc R . . C14 C 0.7397(4) 0.7026(3) 0.1404(3) 0.0391(9) Uani 1 1 d . . . C15 C 1.2036(3) 0.1486(3) 0.6011(3) 0.0332(8) Uani 1 1 d . . . C16 C 1.1041(3) 0.1989(2) 0.5481(2) 0.0310(8) Uani 1 1 d . . . C17 C 1.1251(3) 0.2972(2) 0.5478(3) 0.0332(8) Uani 1 1 d . . . H17 H 1.2041 0.3375 0.5810 0.040 Uiso 1 1 calc R . . C18 C 1.0260(3) 0.3344(3) 0.4971(3) 0.0338(8) Uani 1 1 d . . . H18 H 1.0384 0.3999 0.4944 0.041 Uiso 1 1 calc R . . C19 C 0.9079(3) 0.2737(2) 0.4503(2) 0.0301(8) Uani 1 1 d . . . C20 C 0.8941(3) 0.1762(2) 0.4537(2) 0.0312(8) Uani 1 1 d . . . H20 H 0.8154 0.1349 0.4225 0.037 Uiso 1 1 calc R . . C21 C 0.7994(4) 0.3103(3) 0.3894(3) 0.0340(8) Uani 1 1 d . . . C22 C 0.4179(4) 0.8559(3) 0.2042(3) 0.0470(10) Uani 1 1 d . . . H22A H 0.3925 0.8396 0.2571 0.056 Uiso 1 1 calc R . . H22B H 0.4221 0.7941 0.1593 0.056 Uiso 1 1 calc R . . C23 C 0.3179(3) 0.9064(3) 0.1525(3) 0.0426(9) Uani 1 1 d . . . H23A H 0.3471 0.9298 0.1043 0.051 Uiso 1 1 calc R . . H23B H 0.3051 0.9636 0.1988 0.051 Uiso 1 1 calc R . . C24 C 0.1926(4) 0.8342(3) 0.1036(3) 0.0469(10) Uani 1 1 d . . . H24A H 0.2072 0.7772 0.0582 0.056 Uiso 1 1 calc R . . H24B H 0.1656 0.8104 0.1525 0.056 Uiso 1 1 calc R . . C25 C 0.0849(4) 0.8773(3) 0.0499(3) 0.0443(10) Uani 1 1 d . . . H25A H 0.0607 0.9276 0.0964 0.053 Uiso 1 1 calc R . . H25B H 0.1151 0.9096 0.0072 0.053 Uiso 1 1 calc R . . C26 C -0.0316(3) 0.7991(3) -0.0094(3) 0.0421(9) Uani 1 1 d . . . H26A H -0.0595 0.7657 0.0335 0.051 Uiso 1 1 calc R . . H26B H -0.0068 0.7496 -0.0563 0.051 Uiso 1 1 calc R . . C27 C -0.1442(3) 0.8382(3) -0.0634(3) 0.0410(9) Uani 1 1 d . . . H27A H -0.1172 0.8725 -0.1059 0.049 Uiso 1 1 calc R . . H27B H -0.1721 0.8858 -0.0170 0.049 Uiso 1 1 calc R . . C28 C -0.2548(4) 0.7551(3) -0.1226(3) 0.0427(9) Uani 1 1 d . . . H28A H -0.2816 0.7213 -0.0796 0.051 Uiso 1 1 calc R . . H28B H -0.2258 0.7071 -0.1679 0.051 Uiso 1 1 calc R . . C29 C -0.3687(3) 0.7903(3) -0.1786(3) 0.0429(9) Uani 1 1 d . . . H29A H -0.3958 0.8411 -0.1345 0.052 Uiso 1 1 calc R . . H29B H -0.3450 0.8194 -0.2258 0.052 Uiso 1 1 calc R . . C30 C 0.3925(3) 0.5358(3) 0.1902(3) 0.0416(9) Uani 1 1 d . . . H30A H 0.3599 0.5128 0.2373 0.050 Uiso 1 1 calc R . . H30B H 0.4118 0.4787 0.1479 0.050 Uiso 1 1 calc R . . C31 C 0.2903(3) 0.5778(3) 0.1308(3) 0.0421(9) Uani 1 1 d . . . H31A H 0.3220 0.6009 0.0834 0.051 Uiso 1 1 calc R . . H31B H 0.2694 0.6343 0.1727 0.051 Uiso 1 1 calc R . . C32 C 0.1707(3) 0.4994(3) 0.0789(3) 0.0410(9) Uani 1 1 d . . . H32A H 0.1909 0.4458 0.0331 0.049 Uiso 1 1 calc R . . H32B H 0.1450 0.4717 0.1261 0.049 Uiso 1 1 calc R . . C33 C 0.0601(3) 0.5391(3) 0.0255(3) 0.0420(9) Uani 1 1 d . . . H33A H 0.0855 0.5660 -0.0223 0.050 Uiso 1 1 calc R . . H33B H 0.0406 0.5933 0.0711 0.050 Uiso 1 1 calc R . . Cu1 Cu 0.92940(4) 0.37924(3) 0.24653(3) 0.03599(15) Uani 1 1 d . . . Cu2 Cu 1.0000 0.0000 0.5000 0.0434(2) Uani 1 2 d S . . N1 N 0.9505(3) 0.2375(2) 0.2373(2) 0.0310(7) Uani 1 1 d . . . N2 N 0.9253(3) 0.5195(2) 0.2400(2) 0.0321(7) Uani 1 1 d . . . N3 N 0.9911(3) 0.13900(19) 0.5009(2) 0.0295(7) Uani 1 1 d . . . N4 N 0.5464(3) 0.9189(2) 0.2431(2) 0.0477(9) Uani 1 1 d . . . H4A H 0.5735 0.9291 0.1943 0.072 Uiso 1 1 calc R . . H4B H 0.6004 0.8883 0.2767 0.072 Uiso 1 1 calc R . . H4C H 0.5422 0.9771 0.2817 0.072 Uiso 1 1 calc R . . N5 N -0.4758(3) 0.7045(2) -0.2292(2) 0.0441(8) Uani 1 1 d . . . H5A H -0.4512 0.6587 -0.2706 0.066 Uiso 1 1 calc R . . H5B H -0.5428 0.7257 -0.2614 0.066 Uiso 1 1 calc R . . H5C H -0.4973 0.6781 -0.1858 0.066 Uiso 1 1 calc R . . N6 N 0.5119(3) 0.6088(2) 0.2421(2) 0.0467(8) Uani 1 1 d . . . H6A H 0.5455 0.6270 0.1992 0.070 Uiso 1 1 calc R . . H6B H 0.5673 0.5811 0.2781 0.070 Uiso 1 1 calc R . . H6C H 0.4947 0.6621 0.2801 0.070 Uiso 1 1 calc R . . O1 O 0.7705(2) 0.31867(18) 0.14717(19) 0.0459(7) Uani 1 1 d . . . O2 O 0.6352(3) 0.1749(2) 0.0848(2) 0.0651(9) Uani 1 1 d . . . O3 O 1.2573(3) 0.1086(2) 0.3524(2) 0.0630(9) Uani 1 1 d . . . O4 O 1.1211(3) -0.0197(2) 0.3532(2) 0.0681(9) Uani 1 1 d . . . O5 O 1.1020(2) 0.43305(18) 0.3255(2) 0.0445(7) Uani 1 1 d . . . O6 O 1.2444(3) 0.57186(19) 0.3875(2) 0.0508(7) Uani 1 1 d . . . O7 O 0.6298(3) 0.6497(2) 0.1093(2) 0.0507(7) Uani 1 1 d . . . O8 O 0.7685(3) 0.7854(2) 0.1299(2) 0.0583(8) Uani 1 1 d . . . O9 O 1.1701(2) 0.05582(17) 0.58808(19) 0.0430(7) Uani 1 1 d . . . O10 O 1.3073(2) 0.19859(19) 0.65345(19) 0.0449(7) Uani 1 1 d . . . O11 O 0.8291(2) 0.38930(18) 0.36830(19) 0.0423(6) Uani 1 1 d . . . O12 O 0.6904(2) 0.2591(2) 0.3621(2) 0.0494(7) Uani 1 1 d . . . O13 O 0.4056(3) 0.1078(2) 0.9364(2) 0.0521(7) Uani 1 1 d . . . O14 O 0.5307(3) 0.3728(2) 0.0744(2) 0.0563(8) Uani 1 1 d . . . O15 O 0.6449(3) 0.5030(2) 0.3562(2) 0.0576(8) Uani 1 1 d . . . O16 O 0.5924(3) 0.2721(2) 0.6182(2) 0.0596(8) Uani 1 1 d . . . O17 O 0.5256(3) 0.0947(2) 0.3739(2) 0.0671(9) Uani 1 1 d . . . O18 O 0.6640(4) 0.0932(3) 0.5719(3) 0.0914(12) Uani 1 1 d . . . O19 O 0.4132(3) 0.4280(2) 0.3846(2) 0.0665(9) Uani 1 1 d . . . O20 O 0.3877(4) 0.2868(3) 0.4702(3) 0.0953(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.036(2) 0.042(2) 0.041(2) 0.0065(18) -0.0002(19) 0.0099(19) C2 0.030(2) 0.0335(19) 0.034(2) 0.0074(16) 0.0026(17) 0.0059(17) C3 0.037(2) 0.0299(19) 0.047(2) 0.0069(17) 0.0037(18) 0.0020(17) C4 0.043(2) 0.0285(19) 0.050(2) 0.0115(18) 0.012(2) 0.0086(18) C5 0.036(2) 0.0332(19) 0.039(2) 0.0126(17) 0.0131(18) 0.0115(17) C6 0.029(2) 0.036(2) 0.035(2) 0.0096(16) 0.0071(16) 0.0094(16) C7 0.044(3) 0.040(2) 0.047(2) 0.0116(19) 0.010(2) 0.018(2) C8 0.027(2) 0.036(2) 0.046(2) 0.0160(18) 0.0092(18) 0.0069(17) C9 0.029(2) 0.0341(19) 0.040(2) 0.0129(17) 0.0125(17) 0.0104(17) C10 0.026(2) 0.036(2) 0.045(2) 0.0125(17) 0.0078(17) 0.0043(16) C11 0.035(2) 0.0305(19) 0.048(2) 0.0157(17) 0.0145(19) 0.0094(17) C12 0.035(2) 0.037(2) 0.036(2) 0.0154(17) 0.0139(18) 0.0127(17) C13 0.028(2) 0.036(2) 0.038(2) 0.0137(17) 0.0047(16) 0.0068(16) C14 0.035(2) 0.042(2) 0.044(2) 0.0175(19) 0.0095(19) 0.0143(19) C15 0.025(2) 0.034(2) 0.039(2) 0.0111(17) 0.0034(17) 0.0074(17) C16 0.026(2) 0.0315(18) 0.034(2) 0.0099(16) 0.0048(16) 0.0074(16) C17 0.0254(19) 0.0273(18) 0.040(2) 0.0079(16) 0.0017(16) 0.0009(15) C18 0.035(2) 0.0269(18) 0.040(2) 0.0115(16) 0.0082(17) 0.0074(16) C19 0.030(2) 0.0295(18) 0.0328(19) 0.0103(15) 0.0084(16) 0.0104(16) C20 0.0264(19) 0.0293(18) 0.036(2) 0.0113(16) 0.0026(16) 0.0068(15) C21 0.034(2) 0.035(2) 0.037(2) 0.0145(17) 0.0104(18) 0.0163(18) C22 0.035(2) 0.047(2) 0.054(3) 0.022(2) -0.0009(19) 0.0020(19) C23 0.032(2) 0.042(2) 0.047(2) 0.0098(19) 0.0012(18) 0.0059(18) C24 0.035(2) 0.047(2) 0.054(3) 0.017(2) 0.004(2) 0.0011(19) C25 0.032(2) 0.043(2) 0.050(2) 0.0088(19) 0.0039(19) 0.0032(18) C26 0.029(2) 0.046(2) 0.048(2) 0.0148(19) 0.0060(18) 0.0026(18) C27 0.032(2) 0.041(2) 0.045(2) 0.0111(18) 0.0065(18) 0.0020(17) C28 0.035(2) 0.041(2) 0.049(2) 0.0156(19) 0.0040(19) 0.0074(18) C29 0.035(2) 0.041(2) 0.049(2) 0.0157(19) 0.0020(19) 0.0044(18) C30 0.033(2) 0.034(2) 0.054(2) 0.0116(18) 0.0062(19) 0.0071(17) C31 0.035(2) 0.040(2) 0.048(2) 0.0133(19) 0.0049(19) 0.0047(18) C32 0.035(2) 0.036(2) 0.045(2) 0.0089(18) 0.0018(18) 0.0076(17) C33 0.035(2) 0.040(2) 0.044(2) 0.0082(18) 0.0028(18) 0.0046(17) Cu1 0.0298(3) 0.0287(2) 0.0475(3) 0.0143(2) 0.0033(2) 0.00781(19) Cu2 0.0316(4) 0.0252(3) 0.0603(5) 0.0155(3) -0.0119(3) 0.0038(3) N1 0.0285(17) 0.0284(15) 0.0360(17) 0.0094(13) 0.0078(14) 0.0077(13) N2 0.0272(17) 0.0302(15) 0.0387(17) 0.0111(13) 0.0071(14) 0.0072(14) N3 0.0245(16) 0.0256(14) 0.0338(16) 0.0085(13) 0.0006(13) 0.0040(13) N4 0.0373(19) 0.0452(19) 0.051(2) 0.0133(16) -0.0041(16) 0.0089(16) N5 0.0320(18) 0.0469(19) 0.050(2) 0.0165(16) 0.0021(15) 0.0104(15) N6 0.0313(18) 0.0454(19) 0.060(2) 0.0186(17) 0.0030(16) 0.0077(15) O1 0.0387(16) 0.0344(15) 0.0557(17) 0.0144(13) -0.0043(13) 0.0101(12) O2 0.0392(18) 0.0459(17) 0.082(2) 0.0086(16) -0.0191(17) 0.0025(15) O3 0.0432(19) 0.0568(19) 0.087(2) 0.0285(17) 0.0041(17) 0.0181(16) O4 0.067(2) 0.0501(18) 0.093(2) 0.0419(18) 0.0084(18) 0.0195(16) O5 0.0303(15) 0.0327(14) 0.0676(19) 0.0237(13) 0.0009(13) 0.0039(11) O6 0.0317(16) 0.0401(15) 0.072(2) 0.0196(14) -0.0008(15) 0.0020(13) O7 0.0387(17) 0.0535(17) 0.0583(18) 0.0269(15) 0.0004(14) 0.0087(14) O8 0.0438(17) 0.0541(18) 0.089(2) 0.0457(17) 0.0123(16) 0.0161(14) O9 0.0325(15) 0.0285(14) 0.0566(17) 0.0160(12) -0.0095(13) 0.0032(11) O10 0.0283(15) 0.0386(14) 0.0561(17) 0.0159(13) -0.0082(13) -0.0004(12) O11 0.0420(16) 0.0408(15) 0.0565(17) 0.0278(13) 0.0171(13) 0.0208(12) O12 0.0314(16) 0.0482(16) 0.0648(19) 0.0271(15) -0.0035(14) 0.0080(14) O13 0.0404(16) 0.0459(16) 0.0600(18) 0.0100(14) 0.0032(14) 0.0049(13) O14 0.0494(18) 0.0658(19) 0.0597(19) 0.0227(16) 0.0157(15) 0.0256(15) O15 0.0436(17) 0.0462(16) 0.082(2) 0.0261(16) 0.0060(16) 0.0147(14) O16 0.0518(19) 0.0547(18) 0.070(2) 0.0164(16) 0.0161(16) 0.0041(15) O17 0.061(2) 0.0564(19) 0.075(2) 0.0085(17) 0.0112(17) 0.0176(16) O18 0.115(3) 0.089(3) 0.082(3) 0.032(2) 0.023(2) 0.066(2) O19 0.057(2) 0.083(2) 0.068(2) 0.0277(18) 0.0228(17) 0.0269(18) O20 0.082(3) 0.085(3) 0.115(3) 0.050(2) 0.005(2) 0.006(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.222(4) . ? C1 O1 1.286(5) . ? C1 C2 1.510(5) . ? C2 N1 1.337(4) . ? C2 C3 1.381(5) . ? C3 C4 1.377(5) . ? C3 H3 0.9300 . ? C4 C5 1.380(5) . ? C4 H4 0.9300 . ? C5 C6 1.394(5) . ? C5 C7 1.514(5) . ? C6 N1 1.344(4) . ? C6 H6 0.9300 . ? C7 O3 1.254(5) . ? C7 O4 1.249(5) . ? C8 O6 1.230(4) . ? C8 O5 1.270(4) . ? C8 C9 1.515(5) . ? C9 N2 1.343(4) . ? C9 C10 1.382(5) . ? C10 C11 1.386(5) . ? C10 H10 0.9300 . ? C11 C12 1.383(5) . ? C11 H11 0.9300 . ? C12 C13 1.394(5) . ? C12 C14 1.521(5) . ? C13 N2 1.347(4) . ? C13 H13 0.9300 . ? C14 O8 1.234(4) . ? C14 O7 1.263(4) . ? C15 O10 1.233(4) . ? C15 O9 1.273(4) . ? C15 C16 1.518(5) . ? C16 N3 1.344(4) . ? C16 C17 1.380(5) . ? C17 C18 1.384(5) . ? C17 H17 0.9300 . ? C18 C19 1.388(5) . ? C18 H18 0.9300 . ? C19 C20 1.379(5) . ? C19 C21 1.518(5) . ? C20 N3 1.345(4) . ? C20 H20 0.9300 . ? C21 O12 1.249(4) . ? C21 O11 1.263(4) . ? C22 N4 1.483(5) . ? C22 C23 1.514(5) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.520(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.518(5) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.515(5) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.524(5) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 C28 1.512(5) . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? C28 C29 1.517(5) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 N5 1.494(5) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C30 N6 1.484(5) . ? C30 C31 1.506(5) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.523(5) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C33 1.510(5) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C33 1.525(7) 2_565 ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? Cu1 O5 1.922(2) . ? Cu1 O1 1.931(3) . ? Cu1 N2 2.003(3) . ? Cu1 N1 2.005(3) . ? Cu1 O11 2.336(3) . ? Cu2 O9 1.945(2) 2_756 ? Cu2 O9 1.945(2) . ? Cu2 N3 1.964(3) . ? Cu2 N3 1.964(3) 2_756 ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? N4 H4C 0.8900 . ? N5 H5A 0.8900 . ? N5 H5B 0.8900 . ? N5 H5C 0.8900 . ? N6 H6A 0.8900 . ? N6 H6B 0.8900 . ? N6 H6C 0.8900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.0(4) . . ? O2 C1 C2 119.8(3) . . ? O1 C1 C2 115.3(3) . . ? N1 C2 C3 122.8(3) . . ? N1 C2 C1 114.7(3) . . ? C3 C2 C1 122.5(3) . . ? C4 C3 C2 118.1(4) . . ? C4 C3 H3 121.0 . . ? C2 C3 H3 121.0 . . ? C3 C4 C5 120.3(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 118.0(3) . . ? C4 C5 C7 121.2(3) . . ? C6 C5 C7 120.8(3) . . ? N1 C6 C5 122.0(3) . . ? N1 C6 H6 119.0 . . ? C5 C6 H6 119.0 . . ? O3 C7 O4 126.5(4) . . ? O3 C7 C5 116.9(3) . . ? O4 C7 C5 116.6(4) . . ? O6 C8 O5 124.4(3) . . ? O6 C8 C9 120.1(3) . . ? O5 C8 C9 115.5(3) . . ? N2 C9 C10 122.6(3) . . ? N2 C9 C8 114.2(3) . . ? C10 C9 C8 123.3(3) . . ? C11 C10 C9 118.6(3) . . ? C11 C10 H10 120.7 . . ? C9 C10 H10 120.7 . . ? C12 C11 C10 119.6(3) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 118.5(3) . . ? C11 C12 C14 120.5(3) . . ? C13 C12 C14 121.0(3) . . ? N2 C13 C12 122.1(3) . . ? N2 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? O8 C14 O7 126.3(3) . . ? O8 C14 C12 116.8(3) . . ? O7 C14 C12 116.9(3) . . ? O10 C15 O9 125.2(3) . . ? O10 C15 C16 119.4(3) . . ? O9 C15 C16 115.4(3) . . ? N3 C16 C17 122.1(3) . . ? N3 C16 C15 113.8(3) . . ? C17 C16 C15 124.1(3) . . ? C16 C17 C18 118.4(3) . . ? C16 C17 H17 120.8 . . ? C18 C17 H17 120.8 . . ? C17 C18 C19 119.9(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C20 C19 C18 118.4(3) . . ? C20 C19 C21 120.2(3) . . ? C18 C19 C21 121.2(3) . . ? N3 C20 C19 122.0(3) . . ? N3 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? O12 C21 O11 125.6(3) . . ? O12 C21 C19 118.2(3) . . ? O11 C21 C19 116.2(3) . . ? N4 C22 C23 112.7(3) . . ? N4 C22 H22A 109.1 . . ? C23 C22 H22A 109.1 . . ? N4 C22 H22B 109.1 . . ? C23 C22 H22B 109.1 . . ? H22A C22 H22B 107.8 . . ? C22 C23 C24 110.3(3) . . ? C22 C23 H23A 109.6 . . ? C24 C23 H23A 109.6 . . ? C22 C23 H23B 109.6 . . ? C24 C23 H23B 109.6 . . ? H23A C23 H23B 108.1 . . ? C25 C24 C23 114.8(3) . . ? C25 C24 H24A 108.6 . . ? C23 C24 H24A 108.6 . . ? C25 C24 H24B 108.6 . . ? C23 C24 H24B 108.6 . . ? H24A C24 H24B 107.5 . . ? C26 C25 C24 112.7(3) . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25B 109.0 . . ? C24 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C25 C26 C27 115.2(3) . . ? C25 C26 H26A 108.5 . . ? C27 C26 H26A 108.5 . . ? C25 C26 H26B 108.5 . . ? C27 C26 H26B 108.5 . . ? H26A C26 H26B 107.5 . . ? C26 C27 C28 111.7(3) . . ? C26 C27 H27A 109.3 . . ? C28 C27 H27A 109.3 . . ? C26 C27 H27B 109.3 . . ? C28 C27 H27B 109.3 . . ? H27A C27 H27B 107.9 . . ? C27 C28 C29 113.6(3) . . ? C27 C28 H28A 108.8 . . ? C29 C28 H28A 108.8 . . ? C27 C28 H28B 108.8 . . ? C29 C28 H28B 108.8 . . ? H28A C28 H28B 107.7 . . ? N5 C29 C28 109.8(3) . . ? N5 C29 H29A 109.7 . . ? C28 C29 H29A 109.7 . . ? N5 C29 H29B 109.7 . . ? C28 C29 H29B 109.7 . . ? H29A C29 H29B 108.2 . . ? N6 C30 C31 113.3(3) . . ? N6 C30 H30A 108.9 . . ? C31 C30 H30A 108.9 . . ? N6 C30 H30B 108.9 . . ? C31 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C30 C31 C32 110.9(3) . . ? C30 C31 H31A 109.5 . . ? C32 C31 H31A 109.5 . . ? C30 C31 H31B 109.5 . . ? C32 C31 H31B 109.5 . . ? H31A C31 H31B 108.1 . . ? C33 C32 C31 113.6(3) . . ? C33 C32 H32A 108.8 . . ? C31 C32 H32A 108.8 . . ? C33 C32 H32B 108.8 . . ? C31 C32 H32B 108.8 . . ? H32A C32 H32B 107.7 . . ? C32 C33 C33 113.6(4) . 2_565 ? C32 C33 H33A 108.8 . . ? C33 C33 H33A 108.8 2_565 . ? C32 C33 H33B 108.8 . . ? C33 C33 H33B 108.8 2_565 . ? H33A C33 H33B 107.7 . . ? O5 Cu1 O1 169.01(12) . . ? O5 Cu1 N2 83.46(11) . . ? O1 Cu1 N2 97.25(11) . . ? O5 Cu1 N1 94.12(11) . . ? O1 Cu1 N1 83.38(11) . . ? N2 Cu1 N1 170.46(11) . . ? O5 Cu1 O11 99.42(11) . . ? O1 Cu1 O11 91.42(11) . . ? N2 Cu1 O11 96.30(10) . . ? N1 Cu1 O11 93.20(10) . . ? O9 Cu2 O9 180.00(10) 2_756 . ? O9 Cu2 N3 96.20(10) 2_756 . ? O9 Cu2 N3 83.80(10) . . ? O9 Cu2 N3 83.80(10) 2_756 2_756 ? O9 Cu2 N3 96.20(10) . 2_756 ? N3 Cu2 N3 180.000(1) . 2_756 ? C6 N1 C2 118.7(3) . . ? C6 N1 Cu1 130.4(2) . . ? C2 N1 Cu1 110.4(2) . . ? C13 N2 C9 118.6(3) . . ? C13 N2 Cu1 130.3(2) . . ? C9 N2 Cu1 111.0(2) . . ? C20 N3 C16 119.3(3) . . ? C20 N3 Cu2 128.6(2) . . ? C16 N3 Cu2 111.8(2) . . ? C22 N4 H4A 109.5 . . ? C22 N4 H4B 109.5 . . ? H4A N4 H4B 109.5 . . ? C22 N4 H4C 109.5 . . ? H4A N4 H4C 109.5 . . ? H4B N4 H4C 109.5 . . ? C29 N5 H5A 109.5 . . ? C29 N5 H5B 109.5 . . ? H5A N5 H5B 109.5 . . ? C29 N5 H5C 109.5 . . ? H5A N5 H5C 109.5 . . ? H5B N5 H5C 109.5 . . ? C30 N6 H6A 109.5 . . ? C30 N6 H6B 109.5 . . ? H6A N6 H6B 109.5 . . ? C30 N6 H6C 109.5 . . ? H6A N6 H6C 109.5 . . ? H6B N6 H6C 109.5 . . ? C1 O1 Cu1 114.4(2) . . ? C8 O5 Cu1 115.8(2) . . ? C15 O9 Cu2 114.5(2) . . ? C21 O11 Cu1 118.0(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 N1 -179.6(4) . . . . ? O1 C1 C2 N1 0.3(5) . . . . ? O2 C1 C2 C3 1.0(6) . . . . ? O1 C1 C2 C3 -179.2(4) . . . . ? N1 C2 C3 C4 0.7(6) . . . . ? C1 C2 C3 C4 -179.9(3) . . . . ? C2 C3 C4 C5 -2.1(6) . . . . ? C3 C4 C5 C6 1.5(5) . . . . ? C3 C4 C5 C7 -178.9(3) . . . . ? C4 C5 C6 N1 0.6(5) . . . . ? C7 C5 C6 N1 -179.1(3) . . . . ? C4 C5 C7 O3 157.8(4) . . . . ? C6 C5 C7 O3 -22.5(5) . . . . ? C4 C5 C7 O4 -22.1(5) . . . . ? C6 C5 C7 O4 157.6(4) . . . . ? O6 C8 C9 N2 -179.4(3) . . . . ? O5 C8 C9 N2 1.8(5) . . . . ? O6 C8 C9 C10 1.0(6) . . . . ? O5 C8 C9 C10 -177.8(3) . . . . ? N2 C9 C10 C11 0.1(5) . . . . ? C8 C9 C10 C11 179.7(3) . . . . ? C9 C10 C11 C12 0.5(5) . . . . ? C10 C11 C12 C13 -0.4(5) . . . . ? C10 C11 C12 C14 -179.2(3) . . . . ? C11 C12 C13 N2 -0.4(5) . . . . ? C14 C12 C13 N2 178.4(3) . . . . ? C11 C12 C14 O8 11.8(5) . . . . ? C13 C12 C14 O8 -166.9(4) . . . . ? C11 C12 C14 O7 -168.8(3) . . . . ? C13 C12 C14 O7 12.5(5) . . . . ? O10 C15 C16 N3 -174.0(3) . . . . ? O9 C15 C16 N3 4.9(5) . . . . ? O10 C15 C16 C17 5.5(5) . . . . ? O9 C15 C16 C17 -175.6(3) . . . . ? N3 C16 C17 C18 -0.1(5) . . . . ? C15 C16 C17 C18 -179.5(3) . . . . ? C16 C17 C18 C19 1.7(5) . . . . ? C17 C18 C19 C20 -1.7(5) . . . . ? C17 C18 C19 C21 -176.6(3) . . . . ? C18 C19 C20 N3 0.1(5) . . . . ? C21 C19 C20 N3 175.0(3) . . . . ? C20 C19 C21 O12 16.6(5) . . . . ? C18 C19 C21 O12 -168.6(3) . . . . ? C20 C19 C21 O11 -161.2(3) . . . . ? C18 C19 C21 O11 13.5(5) . . . . ? N4 C22 C23 C24 173.0(3) . . . . ? C22 C23 C24 C25 179.7(4) . . . . ? C23 C24 C25 C26 171.7(3) . . . . ? C24 C25 C26 C27 178.7(3) . . . . ? C25 C26 C27 C28 178.5(3) . . . . ? C26 C27 C28 C29 -179.3(3) . . . . ? C27 C28 C29 N5 -176.1(3) . . . . ? N6 C30 C31 C32 179.6(3) . . . . ? C30 C31 C32 C33 174.6(3) . . . . ? C31 C32 C33 C33 -179.3(4) . . . 2_565 ? C5 C6 N1 C2 -2.0(5) . . . . ? C5 C6 N1 Cu1 168.9(3) . . . . ? C3 C2 N1 C6 1.3(5) . . . . ? C1 C2 N1 C6 -178.1(3) . . . . ? C3 C2 N1 Cu1 -171.3(3) . . . . ? C1 C2 N1 Cu1 9.3(4) . . . . ? O5 Cu1 N1 C6 7.7(3) . . . . ? O1 Cu1 N1 C6 176.9(3) . . . . ? N2 Cu1 N1 C6 82.6(8) . . . . ? O11 Cu1 N1 C6 -92.0(3) . . . . ? O5 Cu1 N1 C2 179.2(2) . . . . ? O1 Cu1 N1 C2 -11.6(2) . . . . ? N2 Cu1 N1 C2 -105.9(7) . . . . ? O11 Cu1 N1 C2 79.5(2) . . . . ? C12 C13 N2 C9 1.0(5) . . . . ? C12 C13 N2 Cu1 -177.7(3) . . . . ? C10 C9 N2 C13 -0.9(5) . . . . ? C8 C9 N2 C13 179.5(3) . . . . ? C10 C9 N2 Cu1 178.0(3) . . . . ? C8 C9 N2 Cu1 -1.6(4) . . . . ? O5 Cu1 N2 C13 179.7(3) . . . . ? O1 Cu1 N2 C13 10.7(3) . . . . ? N1 Cu1 N2 C13 103.9(7) . . . . ? O11 Cu1 N2 C13 -81.5(3) . . . . ? O5 Cu1 N2 C9 0.9(2) . . . . ? O1 Cu1 N2 C9 -168.1(2) . . . . ? N1 Cu1 N2 C9 -74.9(8) . . . . ? O11 Cu1 N2 C9 99.7(2) . . . . ? C19 C20 N3 C16 1.6(5) . . . . ? C19 C20 N3 Cu2 -170.6(2) . . . . ? C17 C16 N3 C20 -1.6(5) . . . . ? C15 C16 N3 C20 177.9(3) . . . . ? C17 C16 N3 Cu2 171.8(3) . . . . ? C15 C16 N3 Cu2 -8.7(4) . . . . ? O9 Cu2 N3 C20 0.3(3) 2_756 . . . ? O9 Cu2 N3 C20 -179.7(3) . . . . ? N3 Cu2 N3 C20 142(12) 2_756 . . . ? O9 Cu2 N3 C16 -172.4(2) 2_756 . . . ? O9 Cu2 N3 C16 7.6(2) . . . . ? N3 Cu2 N3 C16 -31(12) 2_756 . . . ? O2 C1 O1 Cu1 169.6(3) . . . . ? C2 C1 O1 Cu1 -10.3(4) . . . . ? O5 Cu1 O1 C1 89.6(6) . . . . ? N2 Cu1 O1 C1 -177.4(3) . . . . ? N1 Cu1 O1 C1 12.2(3) . . . . ? O11 Cu1 O1 C1 -80.8(3) . . . . ? O6 C8 O5 Cu1 -179.8(3) . . . . ? C9 C8 O5 Cu1 -1.0(4) . . . . ? O1 Cu1 O5 C8 94.5(6) . . . . ? N2 Cu1 O5 C8 0.1(3) . . . . ? N1 Cu1 O5 C8 170.9(3) . . . . ? O11 Cu1 O5 C8 -95.2(3) . . . . ? O10 C15 O9 Cu2 -179.6(3) . . . . ? C16 C15 O9 Cu2 1.6(4) . . . . ? O9 Cu2 O9 C15 151(100) 2_756 . . . ? N3 Cu2 O9 C15 -5.0(3) . . . . ? N3 Cu2 O9 C15 175.0(3) 2_756 . . . ? O12 C21 O11 Cu1 -101.2(4) . . . . ? C19 C21 O11 Cu1 76.4(3) . . . . ? O5 Cu1 O11 C21 -102.8(3) . . . . ? O1 Cu1 O11 C21 75.4(3) . . . . ? N2 Cu1 O11 C21 172.8(3) . . . . ? N1 Cu1 O11 C21 -8.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 24.50 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.543 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 942368' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_25pdc_dap_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H26 Cu N4 O10' _chemical_formula_weight 533.98 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' Cu Cu 0.3201 1.2651 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.3437(2) _cell_length_b 10.6541(2) _cell_length_c 15.0967(3) _cell_angle_alpha 73.9280(10) _cell_angle_beta 89.5720(10) _cell_angle_gamma 79.7710(10) _cell_volume 1115.88(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.589 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 1.043 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 13499 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0218 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 24.49 _reflns_number_total 3602 _reflns_number_gt 3225 _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^)+(0.0374P)^2^+0.7920P] 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 3602 _refine_ls_number_parameters 325 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0776 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.002 _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 C1 C 0.6336(3) -0.1714(2) 0.30609(16) 0.0343(5) Uani 1 1 d . . . C2 C 0.6549(3) -0.0744(2) 0.36021(15) 0.0289(5) Uani 1 1 d . . . C3 C 0.7690(3) -0.1048(2) 0.43757(16) 0.0344(5) Uani 1 1 d . . . H3 H 0.8433 -0.1883 0.4589 0.041 Uiso 1 1 calc R . . C4 C 0.7721(3) -0.0089(2) 0.48352(16) 0.0325(5) Uani 1 1 d . . . H4 H 0.8469 -0.0282 0.5368 0.039 Uiso 1 1 calc R . . C5 C 0.6629(3) 0.1159(2) 0.44964(14) 0.0281(5) Uani 1 1 d . . . C6 C 0.5507(3) 0.1388(2) 0.37123(15) 0.0301(5) Uani 1 1 d . . . H6 H 0.4759 0.2218 0.3482 0.036 Uiso 1 1 calc R . . C7 C 0.6607(3) 0.2275(2) 0.49445(16) 0.0329(5) Uani 1 1 d . . . C8 C 0.2483(3) 0.3038(2) 0.09939(16) 0.0350(5) Uani 1 1 d . . . C9 C 0.2289(3) 0.2051(2) 0.04556(15) 0.0325(5) Uani 1 1 d . . . C10 C 0.1487(4) 0.2391(2) -0.04132(16) 0.0416(6) Uani 1 1 d . . . H10 H 0.0964 0.3270 -0.0706 0.050 Uiso 1 1 calc R . . C11 C 0.1464(4) 0.1412(3) -0.08505(16) 0.0413(6) Uani 1 1 d . . . H11 H 0.0932 0.1629 -0.1443 0.050 Uiso 1 1 calc R . . C12 C 0.2234(3) 0.0109(2) -0.04029(15) 0.0330(5) Uani 1 1 d . . . C13 C 0.2985(3) -0.0166(2) 0.04863(15) 0.0323(5) Uani 1 1 d . . . H13 H 0.3480 -0.1041 0.0802 0.039 Uiso 1 1 calc R . . C14 C 0.2273(3) -0.0990(3) -0.08649(16) 0.0372(6) Uani 1 1 d . . . C15 C -0.1659(4) 0.3522(3) 0.22166(17) 0.0441(6) Uani 1 1 d . . . H15A H -0.0752 0.2714 0.2294 0.053 Uiso 1 1 calc R . . H15B H -0.2678 0.3304 0.2608 0.053 Uiso 1 1 calc R . . C16 C -0.0780(4) 0.4522(2) 0.25262(17) 0.0400(6) Uani 1 1 d . . . H16A H -0.1724 0.5282 0.2533 0.048 Uiso 1 1 calc R . . H16B H 0.0129 0.4833 0.2089 0.048 Uiso 1 1 calc R . . C17 C 0.0156(4) 0.3922(3) 0.34804(17) 0.0473(7) Uani 1 1 d . . . H17A H 0.1040 0.3131 0.3477 0.057 Uiso 1 1 calc R . . H17B H -0.0773 0.3652 0.3917 0.057 Uiso 1 1 calc R . . C18 C 0.1163(4) 0.4857(3) 0.38146(17) 0.0461(6) Uani 1 1 d . . . H18A H 0.0261 0.5585 0.3912 0.055 Uiso 1 1 calc R . . H18B H 0.1811 0.4378 0.4401 0.055 Uiso 1 1 calc R . . C19 C 0.2536(4) 0.5411(3) 0.31320(18) 0.0466(6) Uani 1 1 d . . . H19A H 0.3147 0.4724 0.2867 0.056 Uiso 1 1 calc R . . H19B H 0.1880 0.6134 0.2635 0.056 Uiso 1 1 calc R . . Cu1 Cu 0.40044(4) 0.05950(3) 0.215540(18) 0.03372(11) Uani 1 1 d . . . H10C H 0.337(5) 0.532(4) 0.104(3) 0.115(16) Uiso 1 1 d D . . H10D H 0.416(6) 0.659(3) 0.067(2) 0.110(15) Uiso 1 1 d D . . N1 N 0.5461(3) 0.04606(17) 0.32757(12) 0.0291(4) Uani 1 1 d . . . N2 N 0.3022(3) 0.07847(18) 0.09040(12) 0.0309(4) Uani 1 1 d . . . N3 N -0.2360(3) 0.4019(2) 0.12420(14) 0.0419(5) Uani 1 1 d . . . H3A H -0.3376 0.4634 0.1193 0.063 Uiso 1 1 calc R . . H3B H -0.2627 0.3348 0.1054 0.063 Uiso 1 1 calc R . . H3C H -0.1497 0.4374 0.0892 0.063 Uiso 1 1 calc R . . N4 N 0.3937(3) 0.5900(2) 0.35754(15) 0.0452(5) Uani 1 1 d . . . H4A H 0.3376 0.6510 0.3837 0.068 Uiso 1 1 calc R . . H4B H 0.4688 0.6259 0.3153 0.068 Uiso 1 1 calc R . . H4C H 0.4594 0.5226 0.4005 0.068 Uiso 1 1 calc R . . O1 O 0.5144(2) -0.12713(16) 0.23852(11) 0.0405(4) Uani 1 1 d . . . O2 O 0.7226(3) -0.28448(18) 0.33051(14) 0.0545(5) Uani 1 1 d . . . O3 O 0.5678(3) 0.33721(17) 0.45350(13) 0.0527(5) Uani 1 1 d . . . O4 O 0.7533(3) 0.20231(17) 0.56820(12) 0.0456(4) Uani 1 1 d . . . O5 O 0.3281(3) 0.25463(16) 0.17863(11) 0.0416(4) Uani 1 1 d . . . O6 O 0.1857(3) 0.42302(17) 0.06336(12) 0.0466(4) Uani 1 1 d . . . O7 O 0.3099(3) -0.21267(18) -0.04314(13) 0.0532(5) Uani 1 1 d . . . O8 O 0.1540(3) -0.0692(2) -0.16432(13) 0.0604(6) Uani 1 1 d . . . O9 O 0.1369(3) 0.02465(19) 0.28884(12) 0.0462(4) Uani 1 1 d D . . O10 O 0.4277(3) 0.5806(2) 0.11180(15) 0.0621(6) Uani 1 1 d D . . H9C H 0.048(4) 0.015(3) 0.251(2) 0.082(12) Uiso 1 1 d D . . H9D H 0.163(4) -0.057(2) 0.3298(18) 0.057(9) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0363(13) 0.0331(13) 0.0372(13) -0.0163(10) -0.0020(11) -0.0053(10) C2 0.0285(12) 0.0285(12) 0.0312(11) -0.0100(9) 0.0009(9) -0.0064(9) C3 0.0353(13) 0.0276(12) 0.0378(13) -0.0082(10) -0.0041(10) -0.0003(10) C4 0.0317(13) 0.0340(13) 0.0311(12) -0.0075(10) -0.0043(10) -0.0062(10) C5 0.0293(12) 0.0304(12) 0.0265(11) -0.0086(9) 0.0004(9) -0.0096(9) C6 0.0338(13) 0.0254(12) 0.0298(11) -0.0068(9) -0.0011(10) -0.0032(9) C7 0.0368(13) 0.0312(13) 0.0336(12) -0.0108(10) -0.0019(10) -0.0109(10) C8 0.0416(14) 0.0335(14) 0.0311(12) -0.0104(10) 0.0025(10) -0.0076(11) C9 0.0365(13) 0.0328(13) 0.0276(11) -0.0066(10) 0.0004(10) -0.0079(10) C10 0.0540(16) 0.0336(13) 0.0325(13) -0.0034(10) -0.0091(11) -0.0053(11) C11 0.0491(16) 0.0476(15) 0.0258(12) -0.0073(11) -0.0103(11) -0.0093(12) C12 0.0326(13) 0.0399(14) 0.0303(12) -0.0126(10) 0.0008(10) -0.0123(10) C13 0.0342(13) 0.0329(13) 0.0292(12) -0.0079(10) -0.0057(10) -0.0052(10) C14 0.0399(14) 0.0465(16) 0.0321(13) -0.0173(11) 0.0016(11) -0.0160(12) C15 0.0531(17) 0.0395(14) 0.0392(14) -0.0078(11) -0.0057(12) -0.0115(12) C16 0.0469(15) 0.0356(14) 0.0383(13) -0.0131(11) -0.0035(11) -0.0054(11) C17 0.0512(17) 0.0544(17) 0.0358(14) -0.0064(12) -0.0071(12) -0.0178(13) C18 0.0470(16) 0.0583(17) 0.0335(13) -0.0157(12) -0.0043(11) -0.0064(13) C19 0.0595(18) 0.0424(15) 0.0406(14) -0.0139(12) -0.0040(12) -0.0127(13) Cu1 0.0446(2) 0.03052(17) 0.02655(16) -0.01079(12) -0.00829(12) -0.00325(12) N1 0.0331(11) 0.0258(10) 0.0283(10) -0.0083(8) -0.0020(8) -0.0038(8) N2 0.0352(11) 0.0308(11) 0.0275(9) -0.0090(8) -0.0019(8) -0.0062(8) N3 0.0511(13) 0.0397(12) 0.0398(11) -0.0166(9) -0.0054(10) -0.0119(10) N4 0.0539(14) 0.0371(12) 0.0488(13) -0.0182(10) -0.0044(10) -0.0094(10) O1 0.0486(11) 0.0346(9) 0.0414(9) -0.0186(8) -0.0101(8) -0.0027(8) O2 0.0629(13) 0.0347(11) 0.0650(12) -0.0240(9) -0.0192(10) 0.0098(9) O3 0.0697(13) 0.0321(10) 0.0542(11) -0.0170(9) -0.0233(10) 0.0049(9) O4 0.0609(12) 0.0378(10) 0.0391(10) -0.0146(8) -0.0189(9) -0.0051(8) O5 0.0622(12) 0.0328(9) 0.0296(9) -0.0114(7) -0.0081(8) -0.0033(8) O6 0.0637(12) 0.0320(10) 0.0401(10) -0.0078(8) -0.0091(9) -0.0011(8) O7 0.0732(14) 0.0411(11) 0.0483(11) -0.0193(9) -0.0176(10) -0.0070(10) O8 0.0818(15) 0.0625(13) 0.0413(11) -0.0231(9) -0.0232(10) -0.0104(11) O9 0.0442(11) 0.0492(12) 0.0382(10) -0.0009(9) -0.0065(8) -0.0081(9) O10 0.0678(15) 0.0558(14) 0.0575(13) -0.0093(11) -0.0094(11) -0.0076(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 C1 O2 1.222(3) . ? C1 O1 1.276(3) . ? C1 C2 1.512(3) . ? C2 N1 1.349(3) . ? C2 C3 1.371(3) . ? C3 C4 1.388(3) . ? C3 H3 0.9300 . ? C4 C5 1.386(3) . ? C4 H4 0.9300 . ? C5 C6 1.387(3) . ? C5 C7 1.520(3) . ? C6 N1 1.336(3) . ? C6 H6 0.9300 . ? C7 O3 1.240(3) . ? C7 O4 1.247(3) . ? C8 O6 1.239(3) . ? C8 O5 1.266(3) . ? C8 C9 1.521(3) . ? C9 N2 1.345(3) . ? C9 C10 1.368(3) . ? C10 C11 1.383(4) . ? C10 H10 0.9300 . ? C11 C12 1.382(3) . ? C11 H11 0.9300 . ? C12 C13 1.389(3) . ? C12 C14 1.516(3) . ? C13 N2 1.337(3) . ? C13 H13 0.9300 . ? C14 O8 1.230(3) . ? C14 O7 1.252(3) . ? C15 N3 1.481(3) . ? C15 C16 1.515(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.518(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.529(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.512(4) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 N4 1.474(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? Cu1 O1 1.9509(16) . ? Cu1 N1 1.9655(18) . ? Cu1 O5 1.9712(16) . ? Cu1 N2 1.9717(18) . ? Cu1 O9 2.2588(19) . ? N3 H3A 0.8900 . ? N3 H3B 0.8900 . ? N3 H3C 0.8900 . ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? N4 H4C 0.8900 . ? O9 H9C 0.904(18) . ? O9 H9D 0.904(17) . ? O10 H10C 0.934(19) . ? O10 H10D 0.911(19) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.0(2) . . ? O2 C1 C2 119.8(2) . . ? O1 C1 C2 115.2(2) . . ? N1 C2 C3 121.8(2) . . ? N1 C2 C1 114.06(19) . . ? C3 C2 C1 124.1(2) . . ? C2 C3 C4 119.0(2) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C5 C4 C3 119.6(2) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 118.0(2) . . ? C4 C5 C7 123.1(2) . . ? C6 C5 C7 118.93(19) . . ? N1 C6 C5 122.4(2) . . ? N1 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? O3 C7 O4 125.3(2) . . ? O3 C7 C5 116.7(2) . . ? O4 C7 C5 117.9(2) . . ? O6 C8 O5 125.8(2) . . ? O6 C8 C9 118.5(2) . . ? O5 C8 C9 115.7(2) . . ? N2 C9 C10 121.8(2) . . ? N2 C9 C8 113.86(19) . . ? C10 C9 C8 124.4(2) . . ? C9 C10 C11 119.1(2) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C12 C11 C10 119.7(2) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C11 C12 C13 117.9(2) . . ? C11 C12 C14 121.4(2) . . ? C13 C12 C14 120.7(2) . . ? N2 C13 C12 122.2(2) . . ? N2 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? O8 C14 O7 125.1(2) . . ? O8 C14 C12 117.7(2) . . ? O7 C14 C12 117.1(2) . . ? N3 C15 C16 112.7(2) . . ? N3 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? N3 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C15 C16 C17 111.5(2) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C16 C17 C18 114.3(2) . . ? C16 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? C16 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C17 112.0(2) . . ? C19 C18 H18A 109.2 . . ? C17 C18 H18A 109.2 . . ? C19 C18 H18B 109.2 . . ? C17 C18 H18B 109.2 . . ? H18A C18 H18B 107.9 . . ? N4 C19 C18 111.4(2) . . ? N4 C19 H19A 109.3 . . ? C18 C19 H19A 109.3 . . ? N4 C19 H19B 109.3 . . ? C18 C19 H19B 109.3 . . ? H19A C19 H19B 108.0 . . ? O1 Cu1 N1 83.46(7) . . ? O1 Cu1 O5 168.90(8) . . ? N1 Cu1 O5 96.16(7) . . ? O1 Cu1 N2 94.94(7) . . ? N1 Cu1 N2 168.22(8) . . ? O5 Cu1 N2 83.16(7) . . ? O1 Cu1 O9 96.68(7) . . ? N1 Cu1 O9 95.16(7) . . ? O5 Cu1 O9 94.40(7) . . ? N2 Cu1 O9 96.62(7) . . ? C6 N1 C2 119.19(19) . . ? C6 N1 Cu1 128.62(15) . . ? C2 N1 Cu1 112.18(14) . . ? C13 N2 C9 119.22(19) . . ? C13 N2 Cu1 128.26(15) . . ? C9 N2 Cu1 112.51(15) . . ? C15 N3 H3A 109.5 . . ? C15 N3 H3B 109.5 . . ? H3A N3 H3B 109.5 . . ? C15 N3 H3C 109.5 . . ? H3A N3 H3C 109.5 . . ? H3B N3 H3C 109.5 . . ? C19 N4 H4A 109.5 . . ? C19 N4 H4B 109.5 . . ? H4A N4 H4B 109.5 . . ? C19 N4 H4C 109.5 . . ? H4A N4 H4C 109.5 . . ? H4B N4 H4C 109.5 . . ? C1 O1 Cu1 114.87(14) . . ? C8 O5 Cu1 114.58(15) . . ? Cu1 O9 H9C 113(2) . . ? Cu1 O9 H9D 106.8(19) . . ? H9C O9 H9D 102(3) . . ? H10C O10 H10D 112(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 N1 -178.5(2) . . . . ? O1 C1 C2 N1 -1.1(3) . . . . ? O2 C1 C2 C3 -0.5(4) . . . . ? O1 C1 C2 C3 176.9(2) . . . . ? N1 C2 C3 C4 0.2(3) . . . . ? C1 C2 C3 C4 -177.7(2) . . . . ? C2 C3 C4 C5 -1.2(3) . . . . ? C3 C4 C5 C6 1.4(3) . . . . ? C3 C4 C5 C7 -178.7(2) . . . . ? C4 C5 C6 N1 -0.6(3) . . . . ? C7 C5 C6 N1 179.5(2) . . . . ? C4 C5 C7 O3 174.7(2) . . . . ? C6 C5 C7 O3 -5.4(3) . . . . ? C4 C5 C7 O4 -4.5(3) . . . . ? C6 C5 C7 O4 175.4(2) . . . . ? O6 C8 C9 N2 179.6(2) . . . . ? O5 C8 C9 N2 -0.6(3) . . . . ? O6 C8 C9 C10 0.9(4) . . . . ? O5 C8 C9 C10 -179.3(2) . . . . ? N2 C9 C10 C11 -1.4(4) . . . . ? C8 C9 C10 C11 177.2(2) . . . . ? C9 C10 C11 C12 0.5(4) . . . . ? C10 C11 C12 C13 0.9(4) . . . . ? C10 C11 C12 C14 -178.7(2) . . . . ? C11 C12 C13 N2 -1.6(4) . . . . ? C14 C12 C13 N2 178.0(2) . . . . ? C11 C12 C14 O8 -2.4(4) . . . . ? C13 C12 C14 O8 178.0(2) . . . . ? C11 C12 C14 O7 175.7(2) . . . . ? C13 C12 C14 O7 -4.0(3) . . . . ? N3 C15 C16 C17 -172.2(2) . . . . ? C15 C16 C17 C18 176.9(2) . . . . ? C16 C17 C18 C19 -53.9(3) . . . . ? C17 C18 C19 N4 -159.7(2) . . . . ? C5 C6 N1 C2 -0.4(3) . . . . ? C5 C6 N1 Cu1 -179.10(16) . . . . ? C3 C2 N1 C6 0.6(3) . . . . ? C1 C2 N1 C6 178.65(19) . . . . ? C3 C2 N1 Cu1 179.53(18) . . . . ? C1 C2 N1 Cu1 -2.4(2) . . . . ? O1 Cu1 N1 C6 -177.6(2) . . . . ? O5 Cu1 N1 C6 13.6(2) . . . . ? N2 Cu1 N1 C6 99.6(4) . . . . ? O9 Cu1 N1 C6 -81.43(19) . . . . ? O1 Cu1 N1 C2 3.61(15) . . . . ? O5 Cu1 N1 C2 -165.23(15) . . . . ? N2 Cu1 N1 C2 -79.2(4) . . . . ? O9 Cu1 N1 C2 99.77(15) . . . . ? C12 C13 N2 C9 0.7(3) . . . . ? C12 C13 N2 Cu1 179.58(17) . . . . ? C10 C9 N2 C13 0.8(3) . . . . ? C8 C9 N2 C13 -177.9(2) . . . . ? C10 C9 N2 Cu1 -178.19(19) . . . . ? C8 C9 N2 Cu1 3.1(2) . . . . ? O1 Cu1 N2 C13 8.8(2) . . . . ? N1 Cu1 N2 C13 90.4(4) . . . . ? O5 Cu1 N2 C13 177.8(2) . . . . ? O9 Cu1 N2 C13 -88.6(2) . . . . ? O1 Cu1 N2 C9 -172.35(16) . . . . ? N1 Cu1 N2 C9 -90.7(4) . . . . ? O5 Cu1 N2 C9 -3.34(16) . . . . ? O9 Cu1 N2 C9 90.32(16) . . . . ? O2 C1 O1 Cu1 -178.6(2) . . . . ? C2 C1 O1 Cu1 4.2(3) . . . . ? N1 Cu1 O1 C1 -4.42(17) . . . . ? O5 Cu1 O1 C1 84.3(4) . . . . ? N2 Cu1 O1 C1 163.85(17) . . . . ? O9 Cu1 O1 C1 -98.88(17) . . . . ? O6 C8 O5 Cu1 177.5(2) . . . . ? C9 C8 O5 Cu1 -2.2(3) . . . . ? O1 Cu1 O5 C8 83.8(4) . . . . ? N1 Cu1 O5 C8 171.26(17) . . . . ? N2 Cu1 O5 C8 3.10(17) . . . . ? O9 Cu1 O5 C8 -93.05(17) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 24.49 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.269 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.056 _database_code_depnum_ccdc_archive 'CCDC 942369' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_exp25deta _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C50 H74 Cu3 N12 O36' _chemical_formula_weight 1609.83 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 7.3979(5) _cell_length_b 14.4130(8) _cell_length_c 15.7932(9) _cell_angle_alpha 75.612(5) _cell_angle_beta 82.510(5) _cell_angle_gamma 78.590(5) _cell_volume 1593.06(16) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plates _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.678 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 833 _exptl_absorpt_coefficient_mu 1.103 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 10820 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0608 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5598 _reflns_number_gt 4203 _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^)+(0.0341P)^2^+4.4167P] 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 5598 _refine_ls_number_parameters 459 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1097 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.002 _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 C1 C 0.2515(6) 0.8351(3) 0.0429(3) 0.0321(10) Uani 1 1 d . . . C2 C 0.1912(6) 0.8402(3) 0.1372(3) 0.0278(9) Uani 1 1 d . . . C3 C 0.0808(6) 0.9189(3) 0.1620(3) 0.0337(10) Uani 1 1 d . . . H3 H 0.0329 0.9729 0.1201 0.040 Uiso 1 1 calc R . . C4 C 0.0419(6) 0.9165(3) 0.2510(3) 0.0336(10) Uani 1 1 d . . . H4 H -0.0314 0.9694 0.2693 0.040 Uiso 1 1 calc R . . C5 C 0.1129(5) 0.8347(3) 0.3124(3) 0.0280(9) Uani 1 1 d . . . C6 C 0.2203(6) 0.7581(3) 0.2814(3) 0.0289(10) Uani 1 1 d . . . H6 H 0.2680 0.7026 0.3219 0.035 Uiso 1 1 calc R . . C7 C 0.0789(6) 0.8269(3) 0.4105(3) 0.0348(11) Uani 1 1 d . . . C8 C 0.6331(6) 0.5010(3) 0.2349(3) 0.0292(10) Uani 1 1 d . . . C9 C 0.6821(5) 0.4961(3) 0.1402(3) 0.0269(9) Uani 1 1 d . . . C10 C 0.7997(6) 0.4197(3) 0.1139(3) 0.0327(10) Uani 1 1 d . . . H10 H 0.8561 0.3675 0.1550 0.039 Uiso 1 1 calc R . . C11 C 0.8322(6) 0.4222(3) 0.0253(3) 0.0329(10) Uani 1 1 d . . . H11 H 0.9062 0.3701 0.0060 0.039 Uiso 1 1 calc R . . C12 C 0.7535(5) 0.5031(3) -0.0345(3) 0.0265(9) Uani 1 1 d . . . C13 C 0.6382(5) 0.5774(3) -0.0036(3) 0.0269(9) Uani 1 1 d . . . H13 H 0.5864 0.6322 -0.0436 0.032 Uiso 1 1 calc R . . C14 C 0.7857(6) 0.5079(4) -0.1321(3) 0.0349(11) Uani 1 1 d . . . C15 C 0.2490(6) 0.1632(3) 1.0136(3) 0.0327(10) Uani 1 1 d . . . C16 C 0.2817(5) 0.1690(3) 0.9161(3) 0.0271(9) Uani 1 1 d . . . C17 C 0.1996(6) 0.2444(3) 0.8535(3) 0.0288(10) Uani 1 1 d . . . H17 H 0.1173 0.2961 0.8695 0.035 Uiso 1 1 calc R . . C18 C 0.2420(6) 0.2416(3) 0.7666(3) 0.0294(10) Uani 1 1 d . . . H18 H 0.1901 0.2927 0.7232 0.035 Uiso 1 1 calc R . . C19 C 0.3618(6) 0.1630(3) 0.7431(3) 0.0275(9) Uani 1 1 d . . . C20 C 0.4398(6) 0.0893(3) 0.8102(3) 0.0286(9) Uani 1 1 d . . . H20 H 0.5206 0.0362 0.7959 0.034 Uiso 1 1 calc R . . C21 C 0.4097(6) 0.1558(3) 0.6485(3) 0.0316(10) Uani 1 1 d . . . C22 C 0.8673(6) 0.6422(4) 0.6147(3) 0.0456(13) Uani 1 1 d . . . H22A H 0.9081 0.6820 0.6472 0.055 Uiso 1 1 calc R . . H22B H 0.9171 0.6598 0.5540 0.055 Uiso 1 1 calc R . . C23 C 0.6611(6) 0.6599(3) 0.6194(3) 0.0384(11) Uani 1 1 d . . . H23A H 0.6124 0.6423 0.6802 0.046 Uiso 1 1 calc R . . H23B H 0.6213 0.6190 0.5877 0.046 Uiso 1 1 calc R . . C24 C 0.3830(6) 0.7833(3) 0.6042(3) 0.0419(12) Uani 1 1 d . . . H24A H 0.3568 0.7588 0.6667 0.050 Uiso 1 1 calc R . . H24B H 0.3224 0.7490 0.5735 0.050 Uiso 1 1 calc R . . C25 C 0.3062(6) 0.8904(3) 0.5798(3) 0.0419(12) Uani 1 1 d . . . H25A H 0.3587 0.9246 0.6137 0.050 Uiso 1 1 calc R . . H25B H 0.3385 0.9164 0.5181 0.050 Uiso 1 1 calc R . . Cu1 Cu 0.40991(7) 0.65927(4) 0.14059(3) 0.02971(16) Uani 1 1 d . . . Cu2 Cu 0.5000 0.0000 1.0000 0.0351(2) Uani 1 2 d S . . N1 N 0.2586(4) 0.7602(2) 0.1962(2) 0.0254(8) Uani 1 1 d . . . N2 N 0.5988(4) 0.5726(2) 0.0821(2) 0.0238(7) Uani 1 1 d . . . N3 N 0.4020(4) 0.0928(2) 0.8946(2) 0.0271(8) Uani 1 1 d . . . N4 N 0.9360(5) 0.5383(3) 0.6521(2) 0.0435(10) Uani 1 1 d . . . H4A H 0.8863 0.5217 0.7069 0.065 Uiso 1 1 calc R . . H4B H 1.0587 0.5284 0.6518 0.065 Uiso 1 1 calc R . . H4C H 0.9044 0.5022 0.6200 0.065 Uiso 1 1 calc R . . N5 N 0.5844(5) 0.7640(3) 0.5815(2) 0.0341(9) Uani 1 1 d . . . H5A H 0.6393 0.8029 0.6026 0.041 Uiso 1 1 calc R . . H5B H 0.6081 0.7771 0.5228 0.041 Uiso 1 1 calc R . . N6 N 0.1026(5) 0.9046(3) 0.5981(3) 0.0438(10) Uani 1 1 d . . . H6A H 0.0532 0.8846 0.5587 0.066 Uiso 1 1 calc R . . H6B H 0.0584 0.9673 0.5950 0.066 Uiso 1 1 calc R . . H6C H 0.0736 0.8703 0.6516 0.066 Uiso 1 1 calc R . . O1 O 0.3491(4) 0.7541(2) 0.03293(19) 0.0368(8) Uani 1 1 d . . . O2 O 0.2131(5) 0.9076(2) -0.0158(2) 0.0525(10) Uani 1 1 d . . . O3 O 0.1424(5) 0.7484(2) 0.4597(2) 0.0471(9) Uani 1 1 d . . . O4 O -0.0082(5) 0.9000(2) 0.4366(2) 0.0463(9) Uani 1 1 d . . . O5 O 0.5093(4) 0.5738(2) 0.24754(18) 0.0354(7) Uani 1 1 d . . . O6 O 0.7143(4) 0.4400(2) 0.29315(19) 0.0416(8) Uani 1 1 d . . . O7 O 0.7560(6) 0.5897(3) -0.1827(2) 0.0601(11) Uani 1 1 d . . . O8 O 0.1641(4) 0.5699(3) 0.1565(2) 0.0470(9) Uani 1 1 d . . . O9 O 0.3405(4) 0.0885(2) 1.06244(19) 0.0389(8) Uani 1 1 d . . . O10 O 0.1420(5) 0.2281(2) 1.0411(2) 0.0488(9) Uani 1 1 d . . . O11 O 0.5008(5) 0.0797(2) 0.6329(2) 0.0516(10) Uani 1 1 d . . . O12 O 0.3510(5) 0.2302(2) 0.59124(19) 0.0425(8) Uani 1 1 d . . . O13 O 0.3350(7) 0.4224(3) 0.5876(3) 0.0767(13) Uani 1 1 d . . . O14 O 0.1899(7) 0.5595(3) 0.4519(3) 0.0756(13) Uani 1 1 d . . . O15 O 0.2842(5) 0.1026(2) 0.3472(2) 0.0486(9) Uani 1 1 d . . . O16 O 0.3477(14) 0.2231(4) 0.1874(3) 0.180(4) Uani 1 1 d . . . O17 O 0.6772(14) 0.1290(6) 0.1820(4) 0.193(4) Uani 1 1 d . . . O18 O 0.9268(11) 0.1799(4) 0.2186(4) 0.166(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.038(2) 0.032(3) 0.026(2) -0.008(2) 0.0001(19) -0.003(2) C2 0.030(2) 0.027(2) 0.027(2) -0.0065(19) 0.0017(18) -0.0068(19) C3 0.036(2) 0.030(2) 0.032(3) -0.006(2) -0.0060(19) 0.003(2) C4 0.036(2) 0.028(2) 0.038(3) -0.015(2) 0.002(2) -0.001(2) C5 0.028(2) 0.029(2) 0.028(2) -0.0130(19) -0.0006(18) -0.0021(18) C6 0.032(2) 0.029(2) 0.023(2) -0.0030(18) -0.0029(18) -0.0024(19) C7 0.037(3) 0.038(3) 0.033(3) -0.014(2) 0.002(2) -0.011(2) C8 0.034(2) 0.031(2) 0.024(2) -0.0068(19) -0.0032(18) -0.007(2) C9 0.025(2) 0.030(2) 0.025(2) -0.0055(19) 0.0013(17) -0.0067(18) C10 0.034(2) 0.029(2) 0.030(2) -0.0043(19) -0.0072(19) 0.005(2) C11 0.030(2) 0.032(2) 0.036(3) -0.014(2) -0.0014(19) 0.0024(19) C12 0.024(2) 0.032(2) 0.026(2) -0.0105(19) 0.0025(17) -0.0091(18) C13 0.029(2) 0.027(2) 0.024(2) -0.0050(18) -0.0012(17) -0.0038(18) C14 0.029(2) 0.054(3) 0.026(2) -0.018(2) -0.0001(19) -0.010(2) C15 0.034(2) 0.034(3) 0.028(2) -0.008(2) -0.0002(19) 0.000(2) C16 0.025(2) 0.029(2) 0.025(2) -0.0054(18) -0.0009(17) -0.0022(18) C17 0.029(2) 0.026(2) 0.028(2) -0.0065(19) -0.0002(18) 0.0007(18) C18 0.031(2) 0.026(2) 0.027(2) 0.0010(19) -0.0066(18) -0.0017(19) C19 0.030(2) 0.030(2) 0.024(2) -0.0048(18) -0.0029(17) -0.0103(19) C20 0.032(2) 0.027(2) 0.024(2) -0.0045(18) -0.0010(18) -0.0007(19) C21 0.035(2) 0.030(3) 0.030(2) -0.004(2) -0.0040(19) -0.008(2) C22 0.043(3) 0.044(3) 0.043(3) -0.008(2) 0.003(2) 0.000(2) C23 0.044(3) 0.037(3) 0.029(3) -0.002(2) -0.007(2) 0.000(2) C24 0.042(3) 0.037(3) 0.043(3) -0.011(2) 0.003(2) 0.001(2) C25 0.039(3) 0.035(3) 0.048(3) -0.011(2) -0.004(2) 0.001(2) Cu1 0.0379(3) 0.0272(3) 0.0214(3) -0.0086(2) -0.0014(2) 0.0037(2) Cu2 0.0446(5) 0.0303(4) 0.0189(4) 0.0000(3) 0.0008(3) 0.0110(4) N1 0.0301(19) 0.0221(18) 0.0236(19) -0.0075(15) -0.0001(14) -0.0024(15) N2 0.0287(18) 0.0196(17) 0.0211(18) -0.0041(14) -0.0002(14) -0.0019(14) N3 0.0285(18) 0.0244(19) 0.0247(19) -0.0034(15) -0.0007(15) 0.0004(15) N4 0.043(2) 0.046(3) 0.032(2) -0.0052(19) -0.0002(18) 0.007(2) N5 0.043(2) 0.031(2) 0.026(2) -0.0083(16) -0.0042(16) 0.0012(17) N6 0.047(2) 0.041(2) 0.041(2) -0.0144(19) 0.0008(19) 0.0016(19) O1 0.052(2) 0.0290(17) 0.0237(16) -0.0069(13) -0.0016(14) 0.0063(15) O2 0.071(2) 0.042(2) 0.0292(19) 0.0015(16) 0.0029(17) 0.0093(18) O3 0.070(2) 0.036(2) 0.0289(18) -0.0061(15) 0.0003(16) 0.0005(18) O4 0.059(2) 0.043(2) 0.0372(19) -0.0234(16) 0.0003(16) 0.0055(17) O5 0.0449(18) 0.0363(18) 0.0216(16) -0.0084(14) -0.0033(13) 0.0035(15) O6 0.050(2) 0.044(2) 0.0243(17) 0.0007(15) -0.0105(15) 0.0024(16) O7 0.090(3) 0.062(3) 0.0243(19) -0.0046(18) -0.0024(18) -0.010(2) O8 0.045(2) 0.062(2) 0.041(2) -0.0329(18) 0.0049(15) -0.0047(17) O9 0.0458(19) 0.0394(19) 0.0211(16) -0.0047(14) -0.0004(14) 0.0128(15) O10 0.057(2) 0.047(2) 0.0323(18) -0.0136(16) -0.0023(16) 0.0198(17) O11 0.077(3) 0.041(2) 0.0284(18) -0.0107(16) -0.0022(17) 0.0100(19) O12 0.065(2) 0.0364(19) 0.0226(17) -0.0032(14) -0.0080(15) -0.0026(16) O13 0.131(4) 0.047(2) 0.056(3) -0.006(2) -0.038(3) -0.015(2) O14 0.126(4) 0.042(2) 0.061(3) -0.015(2) -0.022(3) -0.007(2) O15 0.048(2) 0.048(2) 0.050(2) -0.0142(17) -0.0051(16) -0.0033(17) O16 0.439(13) 0.084(4) 0.038(3) -0.006(3) -0.021(5) -0.101(6) O17 0.299(11) 0.161(7) 0.084(5) -0.012(5) 0.033(6) -0.012(7) O18 0.235(8) 0.111(5) 0.072(4) 0.020(3) 0.042(5) 0.070(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 C1 O2 1.226(5) . ? C1 O1 1.280(5) . ? C1 C2 1.513(6) . ? C2 N1 1.343(5) . ? C2 C3 1.371(6) . ? C3 C4 1.391(6) . ? C3 H3 0.9300 . ? C4 C5 1.387(6) . ? C4 H4 0.9300 . ? C5 C6 1.382(6) . ? C5 C7 1.516(6) . ? C6 N1 1.334(5) . ? C6 H6 0.9300 . ? C7 O3 1.247(5) . ? C7 O4 1.254(5) . ? C8 O6 1.230(5) . ? C8 O5 1.287(5) . ? C8 C9 1.509(6) . ? C9 N2 1.346(5) . ? C9 C10 1.376(6) . ? C10 C11 1.381(6) . ? C10 H10 0.9300 . ? C11 C12 1.385(6) . ? C11 H11 0.9300 . ? C12 C13 1.379(5) . ? C12 C14 1.515(6) . ? C13 N2 1.336(5) . ? C13 H13 0.9300 . ? C14 O7 1.246(6) . ? C14 O8 1.247(5) 2_665 ? C15 O10 1.227(5) . ? C15 O9 1.284(5) . ? C15 C16 1.512(6) . ? C16 N3 1.354(5) . ? C16 C17 1.374(6) . ? C17 C18 1.376(6) . ? C17 H17 0.9300 . ? C18 C19 1.390(6) . ? C18 H18 0.9300 . ? C19 C20 1.393(6) . ? C19 C21 1.515(6) . ? C20 N3 1.338(5) . ? C20 H20 0.9300 . ? C21 O11 1.232(5) . ? C21 O12 1.261(5) . ? C22 C23 1.491(6) . ? C22 N4 1.479(6) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 N5 1.495(5) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 N5 1.474(6) . ? C24 C25 1.507(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 N6 1.480(6) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? Cu1 O1 1.940(3) . ? Cu1 O5 1.960(3) . ? Cu1 N1 1.968(3) . ? Cu1 N2 1.978(3) . ? Cu1 O8 2.383(3) . ? Cu2 O9 1.928(3) . ? Cu2 O9 1.928(3) 2_657 ? Cu2 N3 1.977(3) . ? Cu2 N3 1.977(3) 2_657 ? N4 H4A 0.8900 . ? N4 H4B 0.8900 . ? N4 H4C 0.8900 . ? N5 H5A 0.9000 . ? N5 H5B 0.9000 . ? N6 H6A 0.8900 . ? N6 H6B 0.8900 . ? N6 H6C 0.8900 . ? O8 C14 1.247(5) 2_665 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.8(4) . . ? O2 C1 C2 119.3(4) . . ? O1 C1 C2 114.8(4) . . ? N1 C2 C3 122.0(4) . . ? N1 C2 C1 113.9(3) . . ? C3 C2 C1 124.1(4) . . ? C2 C3 C4 118.6(4) . . ? C2 C3 H3 120.7 . . ? C4 C3 H3 120.7 . . ? C5 C4 C3 119.7(4) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 117.6(4) . . ? C6 C5 C7 119.5(4) . . ? C4 C5 C7 122.9(4) . . ? N1 C6 C5 122.9(4) . . ? N1 C6 H6 118.6 . . ? C5 C6 H6 118.6 . . ? O3 C7 O4 124.5(4) . . ? O3 C7 C5 117.4(4) . . ? O4 C7 C5 118.1(4) . . ? O6 C8 O5 124.8(4) . . ? O6 C8 C9 120.1(4) . . ? O5 C8 C9 115.1(4) . . ? N2 C9 C10 121.9(4) . . ? N2 C9 C8 114.4(3) . . ? C10 C9 C8 123.6(4) . . ? C9 C10 C11 118.6(4) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C12 C11 C10 119.4(4) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C13 C12 C11 118.8(4) . . ? C13 C12 C14 120.4(4) . . ? C11 C12 C14 120.7(4) . . ? N2 C13 C12 121.7(4) . . ? N2 C13 H13 119.1 . . ? C12 C13 H13 119.1 . . ? O7 C14 O8 124.4(4) . 2_665 ? O7 C14 C12 117.3(4) . . ? O8 C14 C12 118.3(4) 2_665 . ? O10 C15 O9 124.5(4) . . ? O10 C15 C16 120.0(4) . . ? O9 C15 C16 115.5(4) . . ? N3 C16 C17 122.0(4) . . ? N3 C16 C15 114.0(4) . . ? C17 C16 C15 124.0(4) . . ? C16 C17 C18 118.5(4) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? C17 C18 C19 120.5(4) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C18 C19 C20 117.7(4) . . ? C18 C19 C21 122.4(4) . . ? C20 C19 C21 119.9(4) . . ? N3 C20 C19 121.9(4) . . ? N3 C20 H20 119.0 . . ? C19 C20 H20 119.0 . . ? O11 C21 O12 125.1(4) . . ? O11 C21 C19 118.9(4) . . ? O12 C21 C19 116.0(4) . . ? C23 C22 N4 109.6(4) . . ? C23 C22 H22A 109.7 . . ? N4 C22 H22A 109.7 . . ? C23 C22 H22B 109.7 . . ? N4 C22 H22B 109.7 . . ? H22A C22 H22B 108.2 . . ? C22 C23 N5 111.8(4) . . ? C22 C23 H23A 109.3 . . ? N5 C23 H23A 109.3 . . ? C22 C23 H23B 109.3 . . ? N5 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? N5 C24 C25 111.4(4) . . ? N5 C24 H24A 109.3 . . ? C25 C24 H24A 109.3 . . ? N5 C24 H24B 109.3 . . ? C25 C24 H24B 109.3 . . ? H24A C24 H24B 108.0 . . ? N6 C25 C24 108.9(4) . . ? N6 C25 H25A 109.9 . . ? C24 C25 H25A 109.9 . . ? N6 C25 H25B 109.9 . . ? C24 C25 H25B 109.9 . . ? H25A C25 H25B 108.3 . . ? O1 Cu1 O5 170.12(14) . . ? O1 Cu1 N1 83.28(13) . . ? O5 Cu1 N1 96.97(13) . . ? O1 Cu1 N2 94.76(13) . . ? O5 Cu1 N2 83.16(12) . . ? N1 Cu1 N2 169.28(14) . . ? O1 Cu1 O8 99.08(13) . . ? O5 Cu1 O8 90.77(13) . . ? N1 Cu1 O8 93.54(12) . . ? N2 Cu1 O8 97.18(12) . . ? O9 Cu2 O9 180.00(14) . 2_657 ? O9 Cu2 N3 84.15(13) . . ? O9 Cu2 N3 95.85(13) 2_657 . ? O9 Cu2 N3 95.85(13) . 2_657 ? O9 Cu2 N3 84.15(13) 2_657 2_657 ? N3 Cu2 N3 180.000(1) . 2_657 ? C6 N1 C2 119.0(3) . . ? C6 N1 Cu1 128.4(3) . . ? C2 N1 Cu1 112.5(3) . . ? C13 N2 C9 119.3(3) . . ? C13 N2 Cu1 128.4(3) . . ? C9 N2 Cu1 112.0(3) . . ? C20 N3 C16 119.3(3) . . ? C20 N3 Cu2 129.3(3) . . ? C16 N3 Cu2 111.4(3) . . ? C22 N4 H4A 109.5 . . ? C22 N4 H4B 109.5 . . ? H4A N4 H4B 109.5 . . ? C22 N4 H4C 109.5 . . ? H4A N4 H4C 109.5 . . ? H4B N4 H4C 109.5 . . ? C24 N5 C23 110.1(4) . . ? C24 N5 H5A 109.6 . . ? C23 N5 H5A 109.6 . . ? C24 N5 H5B 109.6 . . ? C23 N5 H5B 109.6 . . ? H5A N5 H5B 108.2 . . ? C25 N6 H6A 109.5 . . ? C25 N6 H6B 109.5 . . ? H6A N6 H6B 109.5 . . ? C25 N6 H6C 109.5 . . ? H6A N6 H6C 109.5 . . ? H6B N6 H6C 109.5 . . ? C1 O1 Cu1 115.4(3) . . ? C8 O5 Cu1 114.8(3) . . ? C14 O8 Cu1 112.5(3) 2_665 . ? C15 O9 Cu2 114.9(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 N1 -172.9(4) . . . . ? O1 C1 C2 N1 3.5(6) . . . . ? O2 C1 C2 C3 5.9(7) . . . . ? O1 C1 C2 C3 -177.6(4) . . . . ? N1 C2 C3 C4 1.7(7) . . . . ? C1 C2 C3 C4 -177.1(4) . . . . ? C2 C3 C4 C5 -0.8(7) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C3 C4 C5 C7 179.2(4) . . . . ? C4 C5 C6 N1 0.5(6) . . . . ? C7 C5 C6 N1 -179.0(4) . . . . ? C6 C5 C7 O3 -3.7(6) . . . . ? C4 C5 C7 O3 176.8(4) . . . . ? C6 C5 C7 O4 175.1(4) . . . . ? C4 C5 C7 O4 -4.3(7) . . . . ? O6 C8 C9 N2 -172.9(4) . . . . ? O5 C8 C9 N2 4.7(5) . . . . ? O6 C8 C9 C10 8.0(7) . . . . ? O5 C8 C9 C10 -174.4(4) . . . . ? N2 C9 C10 C11 -0.1(6) . . . . ? C8 C9 C10 C11 178.9(4) . . . . ? C9 C10 C11 C12 3.2(7) . . . . ? C10 C11 C12 C13 -2.7(6) . . . . ? C10 C11 C12 C14 -179.7(4) . . . . ? C11 C12 C13 N2 -0.9(6) . . . . ? C14 C12 C13 N2 176.1(4) . . . . ? C13 C12 C14 O7 22.1(6) . . . . ? C11 C12 C14 O7 -161.0(4) . . . . ? C13 C12 C14 O8 -156.4(4) . . . 2_665 ? C11 C12 C14 O8 20.6(6) . . . 2_665 ? O10 C15 C16 N3 -179.8(4) . . . . ? O9 C15 C16 N3 1.0(6) . . . . ? O10 C15 C16 C17 0.8(7) . . . . ? O9 C15 C16 C17 -178.5(4) . . . . ? N3 C16 C17 C18 0.0(6) . . . . ? C15 C16 C17 C18 179.4(4) . . . . ? C16 C17 C18 C19 1.5(6) . . . . ? C17 C18 C19 C20 -1.6(6) . . . . ? C17 C18 C19 C21 178.8(4) . . . . ? C18 C19 C20 N3 0.2(6) . . . . ? C21 C19 C20 N3 179.7(4) . . . . ? C18 C19 C21 O11 -172.4(4) . . . . ? C20 C19 C21 O11 8.1(6) . . . . ? C18 C19 C21 O12 7.6(6) . . . . ? C20 C19 C21 O12 -172.0(4) . . . . ? N4 C22 C23 N5 -179.4(4) . . . . ? N5 C24 C25 N6 175.9(4) . . . . ? C5 C6 N1 C2 0.4(6) . . . . ? C5 C6 N1 Cu1 179.3(3) . . . . ? C3 C2 N1 C6 -1.5(6) . . . . ? C1 C2 N1 C6 177.4(4) . . . . ? C3 C2 N1 Cu1 179.4(3) . . . . ? C1 C2 N1 Cu1 -1.7(4) . . . . ? O1 Cu1 N1 C6 -179.0(4) . . . . ? O5 Cu1 N1 C6 -9.0(4) . . . . ? N2 Cu1 N1 C6 -99.0(8) . . . . ? O8 Cu1 N1 C6 82.2(4) . . . . ? O1 Cu1 N1 C2 -0.1(3) . . . . ? O5 Cu1 N1 C2 170.0(3) . . . . ? N2 Cu1 N1 C2 80.0(8) . . . . ? O8 Cu1 N1 C2 -98.8(3) . . . . ? C12 C13 N2 C9 4.0(6) . . . . ? C12 C13 N2 Cu1 -169.5(3) . . . . ? C10 C9 N2 C13 -3.5(6) . . . . ? C8 C9 N2 C13 177.4(4) . . . . ? C10 C9 N2 Cu1 171.0(3) . . . . ? C8 C9 N2 Cu1 -8.1(4) . . . . ? O1 Cu1 N2 C13 -8.8(4) . . . . ? O5 Cu1 N2 C13 -179.1(4) . . . . ? N1 Cu1 N2 C13 -87.8(8) . . . . ? O8 Cu1 N2 C13 91.0(4) . . . . ? O1 Cu1 N2 C9 177.3(3) . . . . ? O5 Cu1 N2 C9 7.0(3) . . . . ? N1 Cu1 N2 C9 98.3(8) . . . . ? O8 Cu1 N2 C9 -82.9(3) . . . . ? C19 C20 N3 C16 1.3(6) . . . . ? C19 C20 N3 Cu2 -178.1(3) . . . . ? C17 C16 N3 C20 -1.4(6) . . . . ? C15 C16 N3 C20 179.1(4) . . . . ? C17 C16 N3 Cu2 178.1(3) . . . . ? C15 C16 N3 Cu2 -1.4(4) . . . . ? O9 Cu2 N3 C20 -179.4(4) . . . . ? O9 Cu2 N3 C20 0.6(4) 2_657 . . . ? N3 Cu2 N3 C20 138(100) 2_657 . . . ? O9 Cu2 N3 C16 1.1(3) . . . . ? O9 Cu2 N3 C16 -178.9(3) 2_657 . . . ? N3 Cu2 N3 C16 -42(100) 2_657 . . . ? C25 C24 N5 C23 170.7(4) . . . . ? C22 C23 N5 C24 -167.9(4) . . . . ? O2 C1 O1 Cu1 172.6(4) . . . . ? C2 C1 O1 Cu1 -3.6(5) . . . . ? O5 Cu1 O1 C1 -89.9(7) . . . . ? N1 Cu1 O1 C1 2.1(3) . . . . ? N2 Cu1 O1 C1 -167.3(3) . . . . ? O8 Cu1 O1 C1 94.7(3) . . . . ? O6 C8 O5 Cu1 178.8(3) . . . . ? C9 C8 O5 Cu1 1.3(5) . . . . ? O1 Cu1 O5 C8 -82.9(8) . . . . ? N1 Cu1 O5 C8 -173.7(3) . . . . ? N2 Cu1 O5 C8 -4.5(3) . . . . ? O8 Cu1 O5 C8 92.6(3) . . . . ? O1 Cu1 O8 C14 100.8(3) . . . 2_665 ? O5 Cu1 O8 C14 -78.4(3) . . . 2_665 ? N1 Cu1 O8 C14 -175.5(3) . . . 2_665 ? N2 Cu1 O8 C14 4.8(3) . . . 2_665 ? O10 C15 O9 Cu2 -179.2(4) . . . . ? C16 C15 O9 Cu2 0.0(5) . . . . ? O9 Cu2 O9 C15 109(100) 2_657 . . . ? N3 Cu2 O9 C15 -0.6(3) . . . . ? N3 Cu2 O9 C15 179.4(3) 2_657 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.639 _refine_diff_density_min -0.628 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 942370' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_cupdctmda _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H34 Cu N4 O13' _chemical_formula_weight 602.05 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 8.6201(7) _cell_length_b 13.1040(7) _cell_length_c 13.3617(13) _cell_angle_alpha 107.296(7) _cell_angle_beta 108.463(8) _cell_angle_gamma 97.992(6) _cell_volume 1320.79(18) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description blocks _exptl_crystal_colour blue _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.514 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 630 _exptl_absorpt_coefficient_mu 0.898 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 8992 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_sigmaI/netI 0.0797 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4660 _reflns_number_gt 3262 _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^)+(0.1501P)^2^+2.0124P] 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 4660 _refine_ls_number_parameters 389 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0917 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.2132 _refine_ls_wR_factor_gt 0.1620 _refine_ls_goodness_of_fit_ref 0.831 _refine_ls_restrained_S_all 0.830 _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 0.42445(8) 0.81868(5) 0.05487(5) 0.0379(3) Uani 1 1 d . . . O1 O 0.3595(5) 0.7381(3) -0.1063(3) 0.0434(9) Uani 1 1 d . . . O3 O 0.8815(5) 0.6847(3) 0.3621(3) 0.0475(10) Uani 1 1 d . . . O7 O 0.0357(5) 0.9804(3) -0.2518(3) 0.0537(11) Uani 1 1 d . . . O5 O 0.5183(5) 0.9105(3) 0.2151(3) 0.0470(10) Uani 1 1 d . . . O2 O 0.3957(6) 0.5939(4) -0.2275(3) 0.0603(12) Uani 1 1 d . . . N1 N 0.5654(5) 0.7119(3) 0.0704(3) 0.0320(9) Uani 1 1 d . . . O4 O 1.0043(5) 0.5778(3) 0.2656(3) 0.0534(11) Uani 1 1 d . . . O6 O 0.5308(5) 1.0742(3) 0.3351(3) 0.0493(10) Uani 1 1 d . . . O8 O -0.0183(6) 1.1315(3) -0.1562(3) 0.0604(12) Uani 1 1 d . . . N3 N 0.9011(5) 0.3470(3) 0.4578(4) 0.0344(10) Uani 1 1 d . . . N2 N 0.3333(5) 0.9470(3) 0.0380(3) 0.0334(9) Uani 1 1 d . . . O9 O 0.1767(5) 0.7276(3) 0.0584(4) 0.0530(10) Uani 1 1 d D . . N4 N 0.1699(6) 1.0036(4) 0.4382(4) 0.0466(12) Uani 1 1 d . . . O13 O 0.0523(7) 0.3700(5) 0.1688(5) 0.0906(19) Uani 1 1 d D . . O12 O 0.3256(7) 0.3772(5) 0.3686(7) 0.0972(19) Uani 1 1 d D . . O11 O 0.6847(7) 0.3330(5) 0.7412(6) 0.0928(19) Uani 1 1 d D . . C7 C 0.8978(6) 0.6317(4) 0.2726(4) 0.0350(11) Uani 1 1 d . . . C12 C 0.1664(6) 1.0478(4) -0.0527(4) 0.0323(11) Uani 1 1 d . . . C5 C 0.7766(6) 0.6339(4) 0.1632(4) 0.0325(11) Uani 1 1 d . . . C2 C 0.5553(6) 0.6445(4) -0.0310(4) 0.0363(11) Uani 1 1 d . . . C14 C 0.0521(6) 1.0547(4) -0.1627(4) 0.0357(11) Uani 1 1 d . . . C6 C 0.6709(6) 0.7058(4) 0.1648(4) 0.0319(11) Uani 1 1 d . . . H6 H 0.6742 0.7509 0.2343 0.038 Uiso 1 1 calc R . . O10 O 0.4545(9) 0.4163(7) 0.6071(6) 0.107(2) Uani 1 1 d . . . C1 C 0.4268(7) 0.6578(4) -0.1322(4) 0.0408(13) Uani 1 1 d . . . C9 C 0.3711(6) 1.0265(4) 0.1399(4) 0.0325(11) Uani 1 1 d . . . C11 C 0.2037(6) 1.1281(4) 0.0520(4) 0.0365(12) Uani 1 1 d . . . H11 H 0.1575 1.1886 0.0568 0.044 Uiso 1 1 calc R . . C8 C 0.4828(7) 1.0049(4) 0.2394(4) 0.0395(12) Uani 1 1 d . . . C13 C 0.2334(6) 0.9575(4) -0.0558(4) 0.0350(11) Uani 1 1 d . . . H13 H 0.2082 0.9022 -0.1254 0.042 Uiso 1 1 calc R . . C4 C 0.7672(7) 0.5673(4) 0.0575(4) 0.0381(12) Uani 1 1 d . . . H4 H 0.8375 0.5198 0.0529 0.046 Uiso 1 1 calc R . . C16 C 0.9786(6) 0.4503(4) 0.4466(4) 0.0364(12) Uani 1 1 d . . . H16A H 0.9001 0.4613 0.3827 0.044 Uiso 1 1 calc R . . H16B H 1.0807 0.4429 0.4322 0.044 Uiso 1 1 calc R . . C10 C 0.3087(7) 1.1190(4) 0.1487(4) 0.0396(12) Uani 1 1 d . . . H10 H 0.3373 1.1742 0.2190 0.047 Uiso 1 1 calc R . . C20 C 0.2547(7) 0.9154(5) 0.4086(5) 0.0520(15) Uani 1 1 d . . . H20A H 0.3256 0.9350 0.3708 0.078 Uiso 1 1 calc R . . H20B H 0.1711 0.8473 0.3593 0.078 Uiso 1 1 calc R . . H20C H 0.3227 0.9066 0.4763 0.078 Uiso 1 1 calc R . . C15 C 0.7308(6) 0.3439(5) 0.4653(5) 0.0434(13) Uani 1 1 d . . . H15A H 0.7421 0.4019 0.5331 0.065 Uiso 1 1 calc R . . H15B H 0.6851 0.2736 0.4670 0.065 Uiso 1 1 calc R . . H15C H 0.6562 0.3542 0.4005 0.065 Uiso 1 1 calc R . . C18 C 0.2957(8) 1.1125(5) 0.5005(6) 0.0613(17) Uani 1 1 d . . . H18A H 0.3725 1.1125 0.5706 0.092 Uiso 1 1 calc R . . H18B H 0.2384 1.1695 0.5159 0.092 Uiso 1 1 calc R . . H18C H 0.3579 1.1258 0.4554 0.092 Uiso 1 1 calc R . . C3 C 0.6542(7) 0.5710(4) -0.0407(4) 0.0391(12) Uani 1 1 d . . . H3 H 0.6453 0.5251 -0.1115 0.047 Uiso 1 1 calc R . . C17 C 0.8913(8) 0.2499(4) 0.3596(5) 0.0489(14) Uani 1 1 d . . . H17A H 0.8241 0.2559 0.2900 0.073 Uiso 1 1 calc R . . H17B H 0.8402 0.1827 0.3648 0.073 Uiso 1 1 calc R . . H17C H 1.0032 0.2490 0.3613 0.073 Uiso 1 1 calc R . . C19 C 0.0655(8) 0.9703(6) 0.4997(6) 0.0644(18) Uani 1 1 d . . . H19A H 0.0128 0.8914 0.4637 0.077 Uiso 1 1 calc R . . H19B H 0.1388 0.9849 0.5771 0.077 Uiso 1 1 calc R . . H8AA H 0.260(7) 0.730(6) 0.127(3) 0.097 Uiso 1 1 d D . . H8AB H 0.125(8) 0.777(5) 0.097(5) 0.097 Uiso 1 1 d D . . H9AA H 0.794(5) 0.371(5) 0.751(7) 0.097 Uiso 1 1 d D . . H9AB H 0.650(8) 0.398(3) 0.766(7) 0.097 Uiso 1 1 d D . . H0BA H 0.455(12) 0.377(7) 0.636(7) 0.097 Uiso 1 1 d D . . H0BB H 0.373(11) 0.402(7) 0.543(7) 0.097 Uiso 1 1 d D . . H3N H 0.973(7) 0.342(4) 0.519(5) 0.038(15) Uiso 1 1 d . . . H4N H 0.098(8) 1.010(5) 0.372(6) 0.065(19) Uiso 1 1 d . . . H12A H 0.31(3) 0.319(13) 0.397(19) 0.34(12) Uiso 1 1 d D . . H13B H 0.047(10) 0.442(3) 0.206(6) 0.09(3) Uiso 1 1 d D . . H13A H -0.03(2) 0.321(15) 0.096(10) 0.41(14) Uiso 1 1 d D . . H12B H 0.26(3) 0.382(18) 0.298(9) 0.38(14) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0421(4) 0.0461(4) 0.0263(4) 0.0151(3) 0.0073(3) 0.0234(3) O1 0.048(2) 0.058(2) 0.0257(18) 0.0176(17) 0.0065(17) 0.0299(18) O3 0.056(2) 0.056(2) 0.0243(19) 0.0113(17) 0.0033(17) 0.0319(19) O7 0.072(3) 0.067(2) 0.027(2) 0.0193(19) 0.0120(19) 0.046(2) O5 0.055(2) 0.056(2) 0.0267(19) 0.0150(17) 0.0053(17) 0.0272(19) O2 0.076(3) 0.072(3) 0.026(2) 0.0120(19) 0.005(2) 0.042(2) N1 0.035(2) 0.039(2) 0.023(2) 0.0141(17) 0.0069(18) 0.0175(18) O4 0.050(2) 0.064(2) 0.048(2) 0.023(2) 0.0099(19) 0.036(2) O6 0.062(3) 0.047(2) 0.027(2) 0.0107(17) 0.0062(18) 0.0103(19) O8 0.082(3) 0.066(3) 0.043(2) 0.024(2) 0.020(2) 0.052(2) N3 0.038(2) 0.029(2) 0.028(2) 0.0109(18) 0.002(2) 0.0094(18) N2 0.036(2) 0.037(2) 0.024(2) 0.0107(18) 0.0071(18) 0.0125(18) O9 0.054(3) 0.053(2) 0.059(3) 0.018(2) 0.027(2) 0.023(2) N4 0.034(2) 0.079(3) 0.037(3) 0.032(3) 0.012(2) 0.021(2) O13 0.081(4) 0.082(4) 0.068(4) -0.012(3) 0.011(3) 0.027(3) O12 0.067(3) 0.102(4) 0.107(5) 0.027(4) 0.017(3) 0.035(3) O11 0.086(4) 0.114(4) 0.143(6) 0.088(4) 0.074(4) 0.062(3) C7 0.032(3) 0.035(2) 0.035(3) 0.014(2) 0.007(2) 0.010(2) C12 0.034(3) 0.037(2) 0.027(3) 0.014(2) 0.011(2) 0.012(2) C5 0.031(3) 0.033(2) 0.030(3) 0.012(2) 0.006(2) 0.009(2) C2 0.029(3) 0.042(3) 0.035(3) 0.017(2) 0.007(2) 0.007(2) C14 0.037(3) 0.041(3) 0.035(3) 0.017(2) 0.013(2) 0.019(2) C6 0.036(3) 0.036(2) 0.025(2) 0.013(2) 0.008(2) 0.014(2) O10 0.115(5) 0.170(7) 0.104(5) 0.088(5) 0.072(5) 0.086(6) C1 0.044(3) 0.045(3) 0.027(3) 0.011(2) 0.006(2) 0.015(2) C9 0.031(3) 0.031(2) 0.027(3) 0.007(2) 0.005(2) 0.001(2) C11 0.043(3) 0.034(2) 0.037(3) 0.017(2) 0.016(2) 0.016(2) C8 0.037(3) 0.049(3) 0.028(3) 0.016(2) 0.005(2) 0.010(2) C13 0.042(3) 0.043(3) 0.021(2) 0.012(2) 0.010(2) 0.018(2) C4 0.044(3) 0.043(3) 0.036(3) 0.020(2) 0.017(2) 0.022(2) C16 0.039(3) 0.034(2) 0.030(3) 0.009(2) 0.008(2) 0.010(2) C10 0.047(3) 0.037(3) 0.026(3) 0.008(2) 0.007(2) 0.008(2) C20 0.042(3) 0.065(4) 0.050(4) 0.030(3) 0.008(3) 0.019(3) C15 0.035(3) 0.055(3) 0.043(3) 0.021(3) 0.015(3) 0.012(2) C18 0.059(4) 0.071(4) 0.053(4) 0.015(3) 0.020(3) 0.032(3) C3 0.045(3) 0.047(3) 0.025(3) 0.012(2) 0.011(2) 0.018(2) C17 0.061(4) 0.038(3) 0.040(3) 0.009(2) 0.013(3) 0.015(3) C19 0.052(4) 0.118(6) 0.051(4) 0.053(4) 0.026(3) 0.040(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.946(3) . ? Cu1 O5 1.946(4) . ? Cu1 N1 1.990(4) . ? Cu1 N2 1.994(4) . ? Cu1 O9 2.318(4) . ? O1 C1 1.282(6) . ? O3 C7 1.254(6) . ? O7 C14 1.245(6) . ? O5 C8 1.287(6) . ? O2 C1 1.217(6) . ? N1 C6 1.334(6) . ? N1 C2 1.348(6) . ? O4 C7 1.243(6) . ? O6 C8 1.224(6) . ? O8 C14 1.241(6) . ? N3 C16 1.495(6) . ? N3 C15 1.498(7) . ? N3 C17 1.501(6) . ? N2 C13 1.335(6) . ? N2 C9 1.351(6) . ? N4 C20 1.474(7) . ? N4 C18 1.482(8) . ? N4 C19 1.500(8) . ? C7 C5 1.516(7) . ? C12 C11 1.383(7) . ? C12 C13 1.383(7) . ? C12 C14 1.525(7) . ? C5 C4 1.392(7) . ? C5 C6 1.398(6) . ? C2 C3 1.376(7) . ? C2 C1 1.527(7) . ? C9 C10 1.382(7) . ? C9 C8 1.505(7) . ? C11 C10 1.373(7) . ? C4 C3 1.384(7) . ? C16 C16 1.516(9) 2_766 ? C19 C19 1.459(12) 2_576 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O5 171.84(17) . . ? O1 Cu1 N1 83.24(15) . . ? O5 Cu1 N1 95.38(15) . . ? O1 Cu1 N2 96.01(15) . . ? O5 Cu1 N2 83.35(15) . . ? N1 Cu1 N2 165.91(17) . . ? O1 Cu1 O9 93.17(16) . . ? O5 Cu1 O9 94.98(17) . . ? N1 Cu1 O9 101.44(16) . . ? N2 Cu1 O9 92.65(15) . . ? C1 O1 Cu1 115.8(3) . . ? C8 O5 Cu1 115.3(3) . . ? C6 N1 C2 119.4(4) . . ? C6 N1 Cu1 128.6(3) . . ? C2 N1 Cu1 111.9(3) . . ? C16 N3 C15 113.8(4) . . ? C16 N3 C17 108.3(4) . . ? C15 N3 C17 110.9(4) . . ? C13 N2 C9 119.7(4) . . ? C13 N2 Cu1 128.8(3) . . ? C9 N2 Cu1 111.3(3) . . ? C20 N4 C18 110.3(4) . . ? C20 N4 C19 107.1(5) . . ? C18 N4 C19 115.5(5) . . ? O4 C7 O3 126.0(5) . . ? O4 C7 C5 117.3(5) . . ? O3 C7 C5 116.8(4) . . ? C11 C12 C13 117.9(4) . . ? C11 C12 C14 122.4(4) . . ? C13 C12 C14 119.7(4) . . ? C4 C5 C6 117.0(4) . . ? C4 C5 C7 122.2(4) . . ? C6 C5 C7 120.8(4) . . ? N1 C2 C3 122.2(5) . . ? N1 C2 C1 114.1(4) . . ? C3 C2 C1 123.7(5) . . ? O8 C14 O7 125.8(5) . . ? O8 C14 C12 118.0(4) . . ? O7 C14 C12 116.2(4) . . ? N1 C6 C5 122.5(4) . . ? O2 C1 O1 125.8(5) . . ? O2 C1 C2 119.6(5) . . ? O1 C1 C2 114.5(4) . . ? N2 C9 C10 121.0(5) . . ? N2 C9 C8 114.8(4) . . ? C10 C9 C8 124.1(4) . . ? C10 C11 C12 120.4(4) . . ? O6 C8 O5 124.9(5) . . ? O6 C8 C9 120.0(5) . . ? O5 C8 C9 115.1(4) . . ? N2 C13 C12 122.1(4) . . ? C3 C4 C5 120.7(4) . . ? N3 C16 C16 110.8(5) . 2_766 ? C11 C10 C9 118.9(5) . . ? C2 C3 C4 118.3(5) . . ? C19 C19 N4 112.0(7) 2_576 . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.093 _refine_diff_density_min -0.457 _refine_diff_density_rms 0.079 _database_code_depnum_ccdc_archive 'CCDC 942371'