data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H36 Cu4 N10 O16' _chemical_formula_weight 1046.89 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 9.1816(3) _cell_length_b 10.7148(4) _cell_length_c 11.2422(3) _cell_angle_alpha 62.331(3) _cell_angle_beta 85.798(3) _cell_angle_gamma 85.028(3) _cell_volume 975.15(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5237 _cell_measurement_theta_min 2.9622 _cell_measurement_theta_max 29.1015 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 530 _exptl_absorpt_coefficient_mu 2.236 _exptl_absorpt_correction_T_min 0.84799 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(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_reflns_number 8631 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3439 _reflns_number_gt 2949 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0542P)^2^+0.6915P] 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 3439 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0434 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.0998 _refine_ls_wR_factor_gt 0.0960 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 0.53564(4) 0.50154(4) 0.34602(4) 0.02795(14) Uani 1 1 d . . . Cu2 Cu 0.31173(5) 0.70339(4) 0.09788(4) 0.03203(15) Uani 1 1 d . . . C1 C 0.6673(5) 0.0882(4) 0.4251(4) 0.0495(10) Uani 1 1 d . . . C2 C 0.7949(5) 0.1206(5) 0.5717(4) 0.0520(11) Uani 1 1 d . . . C3 C 0.7329(4) 0.2538(4) 0.5297(4) 0.0409(9) Uani 1 1 d . . . C4 C 0.6039(4) 0.2235(4) 0.3791(3) 0.0344(8) Uani 1 1 d . . . C5 C 0.4993(4) 0.2875(4) 0.2673(4) 0.0348(8) Uani 1 1 d . . . C6 C 0.3106(4) 0.4613(4) 0.0574(3) 0.0348(8) Uani 1 1 d . . . C7 C 0.2115(4) 0.5678(4) -0.0424(3) 0.0321(8) Uani 1 1 d . . . C8 C 0.1409(4) 0.5409(5) -0.1299(4) 0.0415(9) Uani 1 1 d . . . C9 C 0.0445(5) 0.6428(5) -0.2175(4) 0.0456(10) Uani 1 1 d . . . C10 C 0.0257(5) 0.7680(5) -0.2153(4) 0.0514(11) Uani 1 1 d . . . C11 C 0.1021(5) 0.7920(4) -0.1264(4) 0.0465(10) Uani 1 1 d . . . C12 C 0.2405(6) 1.1397(4) -0.0192(6) 0.0755(16) Uani 1 1 d . . . H12A H 0.1729 1.1882 0.0167 0.113 Uiso 1 1 calc R . . H12B H 0.2263 1.1765 -0.1136 0.113 Uiso 1 1 calc R . . H12C H 0.3388 1.1534 -0.0059 0.113 Uiso 1 1 calc R . . C13 C 0.2152(4) 0.9858(4) 0.0508(4) 0.0417(9) Uani 1 1 d . . . C14 C 0.8192(5) 0.6836(5) 0.4842(5) 0.0573(12) Uani 1 1 d . . . H14A H 0.9173 0.7061 0.4494 0.086 Uiso 1 1 calc R . . H14B H 0.8205 0.6232 0.5794 0.086 Uiso 1 1 calc R . . H14C H 0.7613 0.7690 0.4667 0.086 Uiso 1 1 calc R . . C15 C 0.7541(4) 0.6093(4) 0.4173(3) 0.0333(8) Uani 1 1 d . . . O1 O 0.4612(4) 0.2155(3) 0.2164(4) 0.0736(10) Uani 1 1 d . . . O1W O 0.5282(4) -0.0594(3) 0.2308(4) 0.0682(9) Uani 1 1 d . . . O2 O 0.6235(2) 0.5730(3) 0.4537(2) 0.0328(5) Uani 1 1 d . . . O3 O 0.8246(3) 0.5856(3) 0.3316(3) 0.0551(8) Uani 1 1 d . . . O4 O 0.2990(3) 0.9082(3) 0.0125(3) 0.0439(6) Uani 1 1 d . . . O5 O 0.1195(4) 0.9418(3) 0.1394(3) 0.0647(9) Uani 1 1 d . . . O6 O 0.4446(3) 0.6771(3) 0.2281(3) 0.0358(6) Uani 1 1 d . . . O7 O 0.1076(4) 0.6605(4) 0.2529(4) 0.0545(8) Uani 1 1 d . . . N1 N 0.7652(4) 0.0353(4) 0.5218(4) 0.0590(10) Uani 1 1 d . . . N2 N 0.6368(3) 0.3068(3) 0.4321(3) 0.0320(6) Uani 1 1 d . . . N3 N 0.4589(3) 0.4214(3) 0.2366(3) 0.0308(6) Uani 1 1 d . . . N4 N 0.3654(3) 0.5015(3) 0.1361(3) 0.0294(6) Uani 1 1 d . . . N5 N 0.1946(3) 0.6939(3) -0.0413(3) 0.0348(7) Uani 1 1 d . . . H11 H 0.089(4) 0.879(4) -0.129(3) 0.028(9) Uiso 1 1 d . . . H3 H 0.755(3) 0.302(3) 0.573(3) 0.017(8) Uiso 1 1 d . . . H8 H 0.154(5) 0.460(5) -0.132(4) 0.051(13) Uiso 1 1 d . . . H2 H 0.848(5) 0.088(5) 0.635(5) 0.058(14) Uiso 1 1 d . . . H7A H 0.033(5) 0.639(5) 0.277(4) 0.044(13) Uiso 1 1 d . . . H7B H 0.091(5) 0.744(5) 0.217(5) 0.051(15) Uiso 1 1 d . . . H6A H 0.468(5) 0.735(5) 0.234(4) 0.045(14) Uiso 1 1 d . . . H9 H -0.008(6) 0.616(5) -0.273(5) 0.082(16) Uiso 1 1 d . . . H10 H -0.047(6) 0.836(6) -0.275(6) 0.089(18) Uiso 1 1 d . . . H1 H 0.650(3) 0.039(3) 0.398(3) 0.043(13) Uiso 1 1 d . . . H1WA H 0.5799 -0.0148 0.1723 0.052 Uiso 1 1 d R . . H1WB H 0.4793 0.0048 0.2263 0.052 Uiso 1 1 d R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0283(2) 0.0283(2) 0.0321(2) -0.01777(19) -0.00589(16) 0.00093(16) Cu2 0.0373(3) 0.0255(2) 0.0370(3) -0.0171(2) -0.01020(18) 0.00315(17) C1 0.063(3) 0.032(2) 0.059(3) -0.025(2) -0.020(2) 0.0097(19) C2 0.060(3) 0.048(3) 0.044(2) -0.018(2) -0.026(2) 0.015(2) C3 0.047(2) 0.043(2) 0.035(2) -0.0199(18) -0.0119(16) 0.0043(17) C4 0.0354(19) 0.0300(19) 0.0380(19) -0.0161(16) -0.0055(15) 0.0027(15) C5 0.0390(19) 0.0313(19) 0.0399(19) -0.0210(17) -0.0098(15) 0.0022(15) C6 0.0355(19) 0.034(2) 0.0375(19) -0.0187(17) -0.0052(15) 0.0006(15) C7 0.0329(18) 0.0349(19) 0.0337(18) -0.0203(16) -0.0039(14) 0.0013(15) C8 0.052(2) 0.044(2) 0.038(2) -0.0263(19) -0.0116(17) 0.0016(18) C9 0.049(2) 0.052(3) 0.042(2) -0.027(2) -0.0161(18) 0.0064(19) C10 0.054(3) 0.052(3) 0.048(2) -0.023(2) -0.020(2) 0.015(2) C11 0.055(2) 0.038(2) 0.050(2) -0.023(2) -0.0182(19) 0.0137(19) C12 0.095(4) 0.031(2) 0.091(4) -0.024(3) 0.019(3) -0.002(2) C13 0.055(2) 0.031(2) 0.040(2) -0.0161(18) -0.0082(18) -0.0013(18) C14 0.049(2) 0.082(3) 0.066(3) -0.052(3) -0.002(2) -0.021(2) C15 0.0333(19) 0.0340(19) 0.0342(18) -0.0164(16) -0.0043(14) -0.0037(15) O1 0.096(3) 0.0479(19) 0.096(2) -0.0461(19) -0.053(2) 0.0217(17) O1W 0.092(2) 0.0467(19) 0.073(2) -0.0337(18) 0.0139(19) -0.0163(17) O2 0.0290(12) 0.0388(14) 0.0375(13) -0.0226(11) -0.0016(10) -0.0057(10) O3 0.0469(16) 0.081(2) 0.0589(17) -0.0494(17) 0.0175(14) -0.0254(15) O4 0.0570(16) 0.0287(14) 0.0446(15) -0.0158(12) -0.0040(12) -0.0005(12) O5 0.080(2) 0.0461(18) 0.0632(19) -0.0232(16) 0.0127(17) -0.0031(16) O6 0.0406(15) 0.0271(14) 0.0458(15) -0.0207(13) -0.0131(11) 0.0010(11) O7 0.0374(17) 0.054(2) 0.071(2) -0.0285(19) 0.0122(15) -0.0074(16) N1 0.072(3) 0.045(2) 0.061(2) -0.0246(19) -0.028(2) 0.0169(18) N2 0.0339(15) 0.0318(16) 0.0323(15) -0.0167(13) -0.0036(12) 0.0019(12) N3 0.0330(15) 0.0266(15) 0.0366(15) -0.0178(13) -0.0075(12) 0.0029(12) N4 0.0309(14) 0.0274(15) 0.0321(14) -0.0154(13) -0.0087(12) 0.0031(12) N5 0.0378(16) 0.0318(16) 0.0367(16) -0.0178(14) -0.0074(13) 0.0050(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O6 1.889(3) . ? Cu1 O2 1.953(2) . ? Cu1 N3 1.991(3) . ? Cu1 N2 2.018(3) . ? Cu1 O2 2.427(2) 2_666 ? Cu2 O6 1.879(3) . ? Cu2 O4 1.941(2) . ? Cu2 N5 2.007(3) . ? Cu2 N4 2.022(3) . ? Cu2 O7 2.385(3) . ? C1 N1 1.339(5) . ? C1 C4 1.381(5) . ? C1 H1 0.75(2) . ? C2 N1 1.330(6) . ? C2 C3 1.363(6) . ? C2 H2 0.81(5) . ? C3 N2 1.335(5) . ? C3 H3 0.90(3) . ? C4 N2 1.346(5) . ? C4 C5 1.495(5) . ? C5 O1 1.237(5) . ? C5 N3 1.335(4) . ? C6 N4 1.297(4) . ? C6 C7 1.473(5) . ? C7 N5 1.352(4) . ? C7 C8 1.365(5) . ? C8 C9 1.381(5) . ? C8 H8 0.88(5) . ? C9 C10 1.349(6) . ? C9 H9 0.97(5) . ? C10 C11 1.389(6) . ? C10 H10 0.98(6) . ? C11 N5 1.331(5) . ? C11 H11 0.92(4) . ? C12 C13 1.492(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 O5 1.222(5) . ? C13 O4 1.282(5) . ? C14 C15 1.504(5) . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O3 1.233(4) . ? C15 O2 1.272(4) . ? O1W H1WA 0.7669 . ? O1W H1WB 0.7712 . ? O2 Cu1 2.427(2) 2_666 ? O6 H6A 0.70(4) . ? O7 H7A 0.73(5) . ? O7 H7B 0.80(5) . ? N3 N4 1.365(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Cu1 O2 95.10(11) . . ? O6 Cu1 N3 87.73(11) . . ? O2 Cu1 N3 176.14(11) . . ? O6 Cu1 N2 166.13(12) . . ? O2 Cu1 N2 96.58(11) . . ? N3 Cu1 N2 80.29(11) . . ? O6 Cu1 O2 102.40(10) . 2_666 ? O2 Cu1 O2 76.10(9) . 2_666 ? N3 Cu1 O2 105.90(10) . 2_666 ? N2 Cu1 O2 87.69(10) . 2_666 ? O6 Cu2 O4 96.49(12) . . ? O6 Cu2 N5 167.27(12) . . ? O4 Cu2 N5 93.81(12) . . ? O6 Cu2 N4 87.54(11) . . ? O4 Cu2 N4 162.26(11) . . ? N5 Cu2 N4 80.42(11) . . ? O6 Cu2 O7 92.49(12) . . ? O4 Cu2 O7 98.90(12) . . ? N5 Cu2 O7 93.30(12) . . ? N4 Cu2 O7 98.17(12) . . ? N1 C1 C4 121.9(4) . . ? N1 C1 H1 115(2) . . ? C4 C1 H1 123(2) . . ? N1 C2 C3 123.9(4) . . ? N1 C2 H2 116(3) . . ? C3 C2 H2 119(3) . . ? N2 C3 C2 120.3(4) . . ? N2 C3 H3 122(2) . . ? C2 C3 H3 118(2) . . ? N2 C4 C1 120.8(3) . . ? N2 C4 C5 116.0(3) . . ? C1 C4 C5 123.1(4) . . ? O1 C5 N3 128.6(3) . . ? O1 C5 C4 119.5(3) . . ? N3 C5 C4 111.9(3) . . ? N4 C6 C7 114.7(3) . . ? N5 C7 C8 122.1(3) . . ? N5 C7 C6 115.7(3) . . ? C8 C7 C6 122.2(3) . . ? C7 C8 C9 119.6(4) . . ? C7 C8 H8 122(3) . . ? C9 C8 H8 118(3) . . ? C10 C9 C8 118.4(4) . . ? C10 C9 H9 125(3) . . ? C8 C9 H9 116(3) . . ? C9 C10 C11 120.1(4) . . ? C9 C10 H10 116(3) . . ? C11 C10 H10 124(3) . . ? N5 C11 C10 121.8(4) . . ? N5 C11 H11 120(2) . . ? C10 C11 H11 118(2) . . ? C13 C12 H12A 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O5 C13 O4 124.5(4) . . ? O5 C13 C12 119.5(4) . . ? O4 C13 C12 116.0(4) . . ? C15 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C15 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O3 C15 O2 122.3(3) . . ? O3 C15 C14 121.2(3) . . ? O2 C15 C14 116.5(3) . . ? H1WA O1W H1WB 94.1 . . ? C15 O2 Cu1 114.5(2) . . ? C15 O2 Cu1 138.6(2) . 2_666 ? Cu1 O2 Cu1 103.90(9) . 2_666 ? C13 O4 Cu2 126.1(2) . . ? Cu2 O6 Cu1 124.81(15) . . ? Cu2 O6 H6A 121(4) . . ? Cu1 O6 H6A 114(4) . . ? Cu2 O7 H7A 153(4) . . ? Cu2 O7 H7B 86(3) . . ? H7A O7 H7B 99(5) . . ? C2 N1 C1 115.5(4) . . ? C3 N2 C4 117.4(3) . . ? C3 N2 Cu1 128.6(3) . . ? C4 N2 Cu1 114.0(2) . . ? C5 N3 N4 122.2(3) . . ? C5 N3 Cu1 117.7(2) . . ? N4 N3 Cu1 120.1(2) . . ? C6 N4 N3 125.4(3) . . ? C6 N4 Cu2 115.7(2) . . ? N3 N4 Cu2 118.8(2) . . ? C11 N5 C7 117.9(3) . . ? C11 N5 Cu2 128.6(3) . . ? C7 N5 Cu2 113.4(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.604 _refine_diff_density_min -0.307 _refine_diff_density_rms 0.084