# Electronic Supplementary Material (ESI) for CrystEngComm # 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H48 Cu2 N6 O18 U' _chemical_formula_weight 1265.95 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' U U -9.6767 9.6646 '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 9.5341(7) _cell_length_b 9.9276(7) _cell_length_c 11.9991(9) _cell_angle_alpha 88.762(3) _cell_angle_beta 77.544(3) _cell_angle_gamma 85.953(3) _cell_volume 1106.20(14) _cell_formula_units_Z 1 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9260 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 34.31 _exptl_crystal_description square _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.900 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 4.687 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3754 _exptl_absorpt_correction_T_max 0.4253 _exptl_absorpt_process_details SADABS _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 9724 _diffrn_reflns_av_R_equivalents 0.0292 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 25.30 _reflns_number_total 3972 _reflns_number_gt 3935 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0600P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3972 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0808 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _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 0.1260(4) -0.1544(4) 0.0648(3) 0.0294(7) Uani 1 1 d . . . C2 C 0.0699(4) -0.2613(4) 0.1396(3) 0.0341(8) Uani 1 1 d . . . C3 C -0.0235(5) -0.3471(4) 0.1101(4) 0.0444(9) Uani 1 1 d . . . H3 H -0.0588 -0.4159 0.1599 0.053 Uiso 1 1 calc R . . C4 C -0.0655(5) -0.3309(5) 0.0057(5) 0.0492(11) Uani 1 1 d . . . H4 H -0.1330 -0.3854 -0.0119 0.059 Uiso 1 1 calc R . . C5 C -0.0070(5) -0.2346(5) -0.0707(4) 0.0460(10) Uani 1 1 d . . . H5 H -0.0321 -0.2265 -0.1413 0.055 Uiso 1 1 calc R . . C6 C 0.0907(4) -0.1482(4) -0.0428(3) 0.0347(8) Uani 1 1 d . . . C7 C 0.1570(4) -0.0587(4) -0.1305(3) 0.0385(9) Uani 1 1 d . . . H7 H 0.1289 -0.0607 -0.2000 0.046 Uiso 1 1 calc R . . C8 C 0.3106(5) 0.1074(5) -0.2204(3) 0.0495(11) Uani 1 1 d . . . H8A H 0.2453 0.1857 -0.2252 0.059 Uiso 1 1 calc R . . H8B H 0.3239 0.0565 -0.2905 0.059 Uiso 1 1 calc R . . C9 C 0.4518(5) 0.1510(6) -0.2051(4) 0.0508(11) Uani 1 1 d . . . H9A H 0.5266 0.0799 -0.2297 0.061 Uiso 1 1 calc R . . H9B H 0.4768 0.2309 -0.2511 0.061 Uiso 1 1 calc R . . C10 C 0.5175(4) 0.2661(4) -0.0536(4) 0.0402(9) Uani 1 1 d . . . H10 H 0.5737 0.3149 -0.1114 0.048 Uiso 1 1 calc R . . C11 C 0.4503(4) 0.2225(4) 0.1560(3) 0.0315(7) Uani 1 1 d . . . C12 C 0.5260(4) 0.2951(4) 0.0611(3) 0.0349(8) Uani 1 1 d . . . C13 C 0.6179(5) 0.3933(5) 0.0760(4) 0.0466(10) Uani 1 1 d . . . H13 H 0.6650 0.4409 0.0130 0.056 Uiso 1 1 calc R . . C14 C 0.6400(5) 0.4208(5) 0.1827(4) 0.0521(11) Uani 1 1 d . . . H14 H 0.7015 0.4863 0.1920 0.063 Uiso 1 1 calc R . . C15 C 0.5683(5) 0.3485(5) 0.2768(4) 0.0483(10) Uani 1 1 d . . . H15 H 0.5837 0.3656 0.3490 0.058 Uiso 1 1 calc R . . C16 C 0.4767(4) 0.2538(4) 0.2648(3) 0.0352(8) Uani 1 1 d . . . C17 C 0.0899(6) -0.3859(5) 0.3095(4) 0.0525(12) Uani 1 1 d . . . H17A H -0.0094 -0.4063 0.3150 0.063 Uiso 1 1 calc R . . H17B H 0.1015 -0.3663 0.3857 0.063 Uiso 1 1 calc R . . C18 C 0.1853(7) -0.5064(6) 0.2659(5) 0.0664(14) Uani 1 1 d . . . H18A H 0.1690 -0.5307 0.1929 0.100 Uiso 1 1 calc R . . H18B H 0.1646 -0.5802 0.3185 0.100 Uiso 1 1 calc R . . H18C H 0.2840 -0.4862 0.2579 0.100 Uiso 1 1 calc R . . C19 C 0.4232(5) 0.1984(5) 0.4646(4) 0.0478(10) Uani 1 1 d . . . H19A H 0.5251 0.2047 0.4611 0.057 Uiso 1 1 calc R . . H19B H 0.3925 0.1208 0.5117 0.057 Uiso 1 1 calc R . . C20 C 0.3417(7) 0.3237(6) 0.5190(5) 0.0626(14) Uani 1 1 d . . . H20A H 0.3656 0.3998 0.4696 0.094 Uiso 1 1 calc R . . H20B H 0.3674 0.3383 0.5907 0.094 Uiso 1 1 calc R . . H20C H 0.2402 0.3131 0.5316 0.094 Uiso 1 1 calc R . . Cu1 Cu 0.31129(5) 0.06621(4) 0.01613(3) 0.02909(12) Uani 1 1 d . . . N1 N 0.2502(4) 0.0227(4) -0.1221(3) 0.0376(7) Uani 1 1 d . . . N2 N 0.4411(4) 0.1808(4) -0.0836(3) 0.0367(7) Uani 1 1 d . . . N3 N 0.8823(5) 0.2579(4) 0.4187(3) 0.0479(9) Uani 1 1 d . . . O2 O 0.2072(3) -0.0726(3) 0.1027(2) 0.0323(5) Uani 1 1 d . . . O3 O 0.3605(3) 0.1310(3) 0.1511(2) 0.0354(6) Uani 1 1 d . . . O1 O 0.1186(4) -0.2686(3) 0.2390(2) 0.0431(7) Uani 1 1 d . . . O4 O 0.4016(3) 0.1783(3) 0.3523(2) 0.0446(7) Uani 1 1 d . . . O5 O 0.8103(4) 0.1915(4) 0.5013(3) 0.0545(8) Uani 1 1 d . . . O6 O 0.8401(5) 0.3693(4) 0.3920(4) 0.0764(12) Uani 1 1 d . . . O7 O 0.9992(4) 0.2007(4) 0.3705(3) 0.0606(9) Uani 1 1 d . . . O9 O 0.8117(3) 0.0086(4) 0.6703(3) 0.0436(7) Uani 1 1 d . . . O8 O 1.1006(3) 0.0931(3) 0.5739(3) 0.0439(7) Uani 1 1 d . . . U1 U 1.0000 0.0000 0.5000 0.02824(9) Uani 1 2 d S . . H9C H 0.763(7) -0.060(6) 0.706(5) 0.053(15) Uiso 1 1 d . . . H9D H 0.797(10) 0.030(10) 0.726(8) 0.10(3) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0252(16) 0.0277(17) 0.0329(18) -0.0080(13) -0.0009(13) -0.0003(14) C2 0.0340(19) 0.0293(18) 0.0372(19) -0.0075(14) -0.0028(15) -0.0033(15) C3 0.041(2) 0.035(2) 0.057(3) -0.0082(18) -0.0070(19) -0.0101(17) C4 0.046(2) 0.037(2) 0.069(3) -0.016(2) -0.019(2) -0.0072(19) C5 0.046(2) 0.046(2) 0.049(2) -0.0169(19) -0.017(2) 0.0014(19) C6 0.0309(18) 0.034(2) 0.039(2) -0.0102(15) -0.0068(15) 0.0035(15) C7 0.042(2) 0.045(2) 0.0300(19) -0.0061(15) -0.0116(16) 0.0016(18) C8 0.053(3) 0.069(3) 0.0239(19) 0.0098(18) -0.0031(17) -0.006(2) C9 0.050(2) 0.069(3) 0.028(2) 0.0100(19) 0.0035(17) -0.006(2) C10 0.0319(19) 0.042(2) 0.042(2) 0.0139(17) 0.0027(16) -0.0055(17) C11 0.0278(17) 0.0293(18) 0.0347(19) 0.0001(14) 0.0000(14) -0.0050(14) C12 0.0319(18) 0.0304(19) 0.038(2) 0.0050(15) 0.0015(15) -0.0031(15) C13 0.036(2) 0.043(2) 0.056(3) 0.0088(19) 0.0063(19) -0.0161(18) C14 0.043(2) 0.050(3) 0.063(3) -0.005(2) -0.002(2) -0.026(2) C15 0.040(2) 0.059(3) 0.045(2) -0.011(2) -0.0019(18) -0.018(2) C16 0.0295(18) 0.038(2) 0.036(2) -0.0010(15) -0.0004(15) -0.0114(16) C17 0.076(3) 0.045(3) 0.036(2) 0.0040(18) -0.003(2) -0.027(2) C18 0.073(4) 0.056(3) 0.071(4) 0.019(3) -0.018(3) -0.003(3) C19 0.056(3) 0.056(3) 0.036(2) 0.0045(18) -0.0156(19) -0.017(2) C20 0.078(4) 0.070(4) 0.039(3) -0.007(2) -0.006(2) -0.018(3) Cu1 0.0307(2) 0.0328(3) 0.0224(2) 0.00275(17) -0.00172(17) -0.00616(19) N1 0.0414(18) 0.047(2) 0.0229(15) 0.0015(13) -0.0029(13) -0.0028(15) N2 0.0345(17) 0.0436(19) 0.0293(16) 0.0100(13) 0.0000(13) -0.0074(14) N3 0.060(2) 0.040(2) 0.050(2) 0.0052(16) -0.0257(19) -0.0042(18) O2 0.0383(14) 0.0323(13) 0.0275(12) 0.0009(10) -0.0066(10) -0.0115(11) O3 0.0400(14) 0.0382(15) 0.0282(13) 0.0046(10) -0.0037(11) -0.0177(12) O1 0.0610(19) 0.0336(15) 0.0349(14) 0.0006(11) -0.0068(13) -0.0164(13) O4 0.0521(17) 0.0529(18) 0.0305(14) 0.0015(12) -0.0057(12) -0.0257(14) O5 0.0476(18) 0.058(2) 0.057(2) 0.0000(16) -0.0097(15) -0.0009(16) O6 0.088(3) 0.056(2) 0.093(3) 0.016(2) -0.041(3) 0.001(2) O7 0.063(2) 0.057(2) 0.057(2) 0.0160(16) -0.0030(17) -0.0038(18) O9 0.0454(16) 0.0528(19) 0.0287(15) -0.0093(13) 0.0072(12) -0.0220(14) O8 0.0420(16) 0.0562(19) 0.0364(15) -0.0072(13) -0.0091(12) -0.0182(14) U1 0.02770(13) 0.03356(14) 0.02390(13) -0.00126(7) -0.00371(8) -0.01045(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 1.312(5) . ? C1 C6 1.402(5) . ? C1 C2 1.431(6) . ? C2 O1 1.370(5) . ? C2 C3 1.378(6) . ? C3 C4 1.397(7) . ? C3 H3 0.9300 . ? C4 C5 1.372(8) . ? C4 H4 0.9300 . ? C5 C6 1.406(6) . ? C5 H5 0.9300 . ? C6 C7 1.431(6) . ? C7 N1 1.264(6) . ? C7 H7 0.9300 . ? C8 N1 1.470(5) . ? C8 C9 1.492(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.474(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.261(6) . ? C10 C12 1.432(6) . ? C10 H10 0.9300 . ? C11 O3 1.303(5) . ? C11 C12 1.421(5) . ? C11 C16 1.426(5) . ? C12 C13 1.395(7) . ? C13 C14 1.377(7) . ? C13 H13 0.9300 . ? C14 C15 1.400(7) . ? C14 H14 0.9300 . ? C15 C16 1.358(6) . ? C15 H15 0.9300 . ? C16 O4 1.376(5) . ? C17 O1 1.431(5) . ? C17 C18 1.483(8) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 O4 1.426(5) . ? C19 C20 1.503(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? Cu1 O2 1.910(3) . ? Cu1 O3 1.916(3) . ? Cu1 N2 1.939(3) . ? Cu1 N1 1.940(3) . ? N3 O6 1.211(6) . ? N3 O7 1.243(6) . ? N3 O5 1.277(6) . ? O5 U1 2.527(3) . ? O7 U1 2.501(3) . ? O9 U1 2.410(3) . ? O9 H9C 0.90(7) . ? O9 H9D 0.69(9) . ? O8 U1 1.757(3) . ? U1 O8 1.757(3) 2_756 ? U1 O9 2.411(3) 2_756 ? U1 O7 2.501(3) 2_756 ? U1 O5 2.527(3) 2_756 ? U1 N3 2.954(4) 2_756 ? 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 C6 126.1(4) . . ? O2 C1 C2 117.1(3) . . ? C6 C1 C2 116.8(3) . . ? O1 C2 C3 125.0(4) . . ? O1 C2 C1 113.8(3) . . ? C3 C2 C1 121.2(4) . . ? C2 C3 C4 120.2(4) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 119.9(4) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 121.1(4) . . ? C1 C6 C7 121.8(4) . . ? C5 C6 C7 117.1(4) . . ? N1 C7 C6 125.9(4) . . ? N1 C7 H7 117.0 . . ? C6 C7 H7 117.0 . . ? N1 C8 C9 108.4(3) . . ? N1 C8 H8A 110.0 . . ? C9 C8 H8A 110.0 . . ? N1 C8 H8B 110.0 . . ? C9 C8 H8B 110.0 . . ? H8A C8 H8B 108.4 . . ? N2 C9 C8 109.0(4) . . ? N2 C9 H9A 109.9 . . ? C8 C9 H9A 109.9 . . ? N2 C9 H9B 109.9 . . ? C8 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? N2 C10 C12 126.3(4) . . ? N2 C10 H10 116.9 . . ? C12 C10 H10 116.9 . . ? O3 C11 C12 125.4(4) . . ? O3 C11 C16 118.2(3) . . ? C12 C11 C16 116.3(4) . . ? C13 C12 C11 120.8(4) . . ? C13 C12 C10 117.3(4) . . ? C11 C12 C10 121.8(4) . . ? C14 C13 C12 121.0(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 118.9(4) . . ? C13 C14 H14 120.5 . . ? C15 C14 H14 120.5 . . ? C16 C15 C14 121.2(4) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 O4 125.2(4) . . ? C15 C16 C11 121.7(4) . . ? O4 C16 C11 113.1(3) . . ? O1 C17 C18 113.2(4) . . ? O1 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? O1 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C19 C20 112.4(4) . . ? O4 C19 H19A 109.1 . . ? C20 C19 H19A 109.1 . . ? O4 C19 H19B 109.1 . . ? C20 C19 H19B 109.1 . . ? H19A C19 H19B 107.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O2 Cu1 O3 90.54(11) . . ? O2 Cu1 N2 169.74(14) . . ? O3 Cu1 N2 93.06(13) . . ? O2 Cu1 N1 93.09(13) . . ? O3 Cu1 N1 172.91(14) . . ? N2 Cu1 N1 84.40(15) . . ? C7 N1 C8 119.9(4) . . ? C7 N1 Cu1 126.4(3) . . ? C8 N1 Cu1 113.3(3) . . ? C10 N2 C9 121.1(4) . . ? C10 N2 Cu1 126.7(3) . . ? C9 N2 Cu1 112.0(3) . . ? O6 N3 O7 123.2(5) . . ? O6 N3 O5 121.9(5) . . ? O7 N3 O5 114.9(4) . . ? C1 O2 Cu1 125.8(2) . . ? C11 O3 Cu1 126.6(2) . . ? C2 O1 C17 117.8(3) . . ? C16 O4 C19 117.9(3) . . ? N3 O5 U1 96.3(3) . . ? N3 O7 U1 98.5(3) . . ? U1 O9 H9C 128(4) . . ? U1 O9 H9D 142(8) . . ? H9C O9 H9D 79(8) . . ? O8 U1 O8 180.0 . 2_756 ? O8 U1 O9 87.56(13) . . ? O8 U1 O9 92.44(13) 2_756 . ? O8 U1 O9 92.44(13) . 2_756 ? O8 U1 O9 87.56(13) 2_756 2_756 ? O9 U1 O9 180.0 . 2_756 ? O8 U1 O7 86.41(15) . . ? O8 U1 O7 93.59(15) 2_756 . ? O9 U1 O7 115.13(12) . . ? O9 U1 O7 64.87(12) 2_756 . ? O8 U1 O7 93.59(15) . 2_756 ? O8 U1 O7 86.41(15) 2_756 2_756 ? O9 U1 O7 64.87(12) . 2_756 ? O9 U1 O7 115.13(12) 2_756 2_756 ? O7 U1 O7 179.999(1) . 2_756 ? O8 U1 O5 86.67(14) . 2_756 ? O8 U1 O5 93.33(14) 2_756 2_756 ? O9 U1 O5 113.92(12) . 2_756 ? O9 U1 O5 66.08(12) 2_756 2_756 ? O7 U1 O5 130.02(12) . 2_756 ? O7 U1 O5 49.98(12) 2_756 2_756 ? O8 U1 O5 93.33(14) . . ? O8 U1 O5 86.67(14) 2_756 . ? O9 U1 O5 66.08(12) . . ? O9 U1 O5 113.92(12) 2_756 . ? O7 U1 O5 49.98(12) . . ? O7 U1 O5 130.02(12) 2_756 . ? O5 U1 O5 179.999(1) 2_756 . ? O8 U1 N3 91.54(13) . 2_756 ? O8 U1 N3 88.47(13) 2_756 2_756 ? O9 U1 N3 89.23(12) . 2_756 ? O9 U1 N3 90.77(12) 2_756 2_756 ? O7 U1 N3 155.40(12) . 2_756 ? O7 U1 N3 24.60(12) 2_756 2_756 ? O5 U1 N3 25.44(12) 2_756 2_756 ? O5 U1 N3 154.56(12) . 2_756 ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.30 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.257 _refine_diff_density_min -2.010 _refine_diff_density_rms 0.149 _database_code_depnum_ccdc_archive 'CCDC 954920' ####################################################################### # # 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_2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 Cu N5 O12 U' _chemical_formula_weight 867.07 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' H H 0.0000 0.0000 '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' U U -9.6767 9.6646 '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/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.1507(8) _cell_length_b 15.0173(12) _cell_length_c 10.8775(9) _cell_angle_alpha 90.00 _cell_angle_beta 102.155(3) _cell_angle_gamma 90.00 _cell_volume 1461.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9418 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.65 _exptl_crystal_description square _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.971 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 834 _exptl_absorpt_coefficient_mu 6.330 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2899 _exptl_absorpt_correction_T_max 0.3365 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 23320 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0431 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 30.40 _reflns_number_total 4528 _reflns_number_gt 3654 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0750P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4528 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1162 _refine_ls_wR_factor_gt 0.1034 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _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 0.2624(5) 0.0826(3) 0.5652(4) 0.0378(10) Uani 1 1 d . . . C2 C 0.1776(6) 0.0403(3) 0.6431(5) 0.0456(11) Uani 1 1 d . . . C3 C 0.1316(7) -0.0469(4) 0.6208(6) 0.0589(15) Uani 1 1 d . . . H3 H 0.0733 -0.0736 0.6709 0.071 Uiso 1 1 calc R . . C4 C 0.4431(11) 0.2500 0.1888(8) 0.069(3) Uani 1 2 d S . . H4A H 0.4849 0.2500 0.1140 0.082 Uiso 1 2 calc SR . . H4B H 0.3351 0.2500 0.1620 0.082 Uiso 1 2 calc SR . . C5 C 0.4901(11) 0.1677(6) 0.2610(7) 0.083(2) Uani 1 1 d . . . H5A H 0.4759 0.1174 0.2038 0.100 Uiso 1 1 calc R . . H5B H 0.5958 0.1717 0.2987 0.100 Uiso 1 1 calc R . . C6 C 0.3772(7) 0.0701(4) 0.3782(5) 0.0545(14) Uani 1 1 d . . . H6 H 0.4124 0.0292 0.3271 0.065 Uiso 1 1 calc R . . C7 C 0.2969(6) 0.0329(3) 0.4661(5) 0.0471(12) Uani 1 1 d . . . C8 C 0.2526(8) -0.0560(4) 0.4485(6) 0.0597(15) Uani 1 1 d . . . H8 H 0.2789 -0.0887 0.3839 0.072 Uiso 1 1 calc R . . C9 C 0.1719(9) -0.0948(4) 0.5243(7) 0.0683(18) Uani 1 1 d . . . H9 H 0.1433 -0.1541 0.5117 0.082 Uiso 1 1 calc R . . C10 C 0.0684(8) 0.0497(5) 0.8225(6) 0.0659(17) Uani 1 1 d . . . H10A H 0.1315 0.0035 0.8680 0.079 Uiso 1 1 calc R . . H10B H -0.0245 0.0229 0.7788 0.079 Uiso 1 1 calc R . . C11 C 0.0382(13) 0.1204(6) 0.9114(9) 0.112(4) Uani 1 1 d . . . H11A H -0.0170 0.1682 0.8645 0.168 Uiso 1 1 calc R . . H11B H 0.1313 0.1428 0.9591 0.168 Uiso 1 1 calc R . . H11C H -0.0190 0.0955 0.9676 0.168 Uiso 1 1 calc R . . C12 C -0.0030(9) 0.2500 0.2494(8) 0.0483(16) Uani 1 2 d S . . C13 C -0.1332(12) 0.2500 0.1481(10) 0.083(3) Uani 1 2 d S . . H13A H -0.2132 0.2187 0.1739 0.100 Uiso 0.50 1 d PR . . H13B H -0.1634 0.3103 0.1268 0.100 Uiso 0.50 1 d PR . . H13C H -0.1096 0.2210 0.0760 0.100 Uiso 0.50 1 d PR . . Cu1 Cu 0.34133(9) 0.2500 0.45642(7) 0.03541(18) Uani 1 2 d S . . N1 N 0.4069(5) 0.1516(3) 0.3605(4) 0.0500(11) Uani 1 1 d . . . N2 N 0.0937(8) 0.2500 0.3298(8) 0.0643(19) Uani 1 2 d S . . N3 N 0.5818(6) 0.4109(3) 0.8948(4) 0.0543(12) Uani 1 1 d . . . O1 O 0.1425(5) 0.0930(3) 0.7345(4) 0.0531(9) Uani 1 1 d . . . O2 O 0.3052(4) 0.1670(2) 0.5868(3) 0.0367(7) Uani 1 1 d . . . O3 O 0.4863(5) 0.4147(3) 0.7940(4) 0.0537(10) Uani 1 1 d . . . O4 O 0.6456(7) 0.4784(3) 0.9430(6) 0.096(2) Uani 1 1 d . . . O5 O 0.6090(5) 0.3355(3) 0.9424(4) 0.0587(11) Uani 1 1 d . . . O6 O 0.5938(7) 0.2500 0.6874(5) 0.0531(14) Uani 1 2 d S . . O7 O 0.3084(6) 0.2500 0.8577(5) 0.0441(11) Uani 1 2 d S . . U1 U 0.44292(3) 0.2500 0.76630(2) 0.03464(10) Uani 1 2 d S . . 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 0.041(2) 0.031(2) 0.039(2) -0.0017(17) 0.0008(19) 0.0020(18) C2 0.050(3) 0.037(3) 0.045(3) 0.003(2) 0.001(2) -0.003(2) C3 0.068(4) 0.041(3) 0.065(4) 0.008(3) 0.008(3) -0.008(3) C4 0.064(5) 0.110(8) 0.036(4) 0.000 0.022(4) 0.000 C5 0.106(6) 0.086(6) 0.076(5) -0.003(4) 0.062(5) 0.014(5) C6 0.071(4) 0.050(3) 0.042(3) -0.011(2) 0.012(3) 0.017(3) C7 0.054(3) 0.040(3) 0.043(3) -0.006(2) 0.001(2) 0.007(2) C8 0.080(4) 0.040(3) 0.055(3) -0.013(2) 0.005(3) 0.007(3) C9 0.088(5) 0.030(3) 0.078(4) -0.007(3) -0.002(4) -0.004(3) C10 0.075(4) 0.068(4) 0.060(4) 0.014(3) 0.026(3) -0.011(3) C11 0.170(10) 0.083(6) 0.117(7) -0.011(5) 0.106(8) -0.032(6) C12 0.046(4) 0.048(4) 0.050(4) 0.000 0.009(4) 0.000 C13 0.067(6) 0.113(9) 0.059(6) 0.000 -0.011(5) 0.000 Cu1 0.0413(4) 0.0384(4) 0.0267(4) 0.000 0.0077(3) 0.000 N1 0.059(3) 0.056(3) 0.040(2) -0.0025(19) 0.022(2) 0.010(2) N2 0.048(4) 0.080(5) 0.061(5) 0.000 0.002(4) 0.000 N3 0.064(3) 0.044(3) 0.048(3) -0.0034(19) -0.003(2) -0.013(2) O1 0.069(3) 0.043(2) 0.051(2) 0.0024(16) 0.0220(19) -0.0095(18) O2 0.0480(18) 0.0326(16) 0.0289(15) -0.0006(12) 0.0068(13) -0.0027(13) O3 0.069(2) 0.042(2) 0.043(2) 0.0027(15) -0.0048(18) -0.0084(18) O4 0.122(5) 0.054(3) 0.089(4) -0.008(3) -0.029(3) -0.030(3) O5 0.076(3) 0.046(2) 0.043(2) 0.0026(16) -0.0127(19) -0.0064(19) O6 0.052(3) 0.076(4) 0.033(3) 0.000 0.012(2) 0.000 O7 0.057(3) 0.041(3) 0.034(2) 0.000 0.009(2) 0.000 U1 0.03972(15) 0.03698(15) 0.02654(14) 0.000 0.00540(9) 0.000 _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 1.332(6) . ? C1 C7 1.401(7) . ? C1 C2 1.414(7) . ? C2 O1 1.360(7) . ? C2 C3 1.382(8) . ? C3 C9 1.385(9) . ? C3 H3 0.9300 . ? C4 C5 1.479(9) 4_565 ? C4 C5 1.479(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.469(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 N1 1.277(8) . ? C6 C7 1.436(8) . ? C6 H6 0.9300 . ? C7 C8 1.396(8) . ? C8 C9 1.349(10) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 O1 1.440(7) . ? C10 C11 1.501(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.105(10) . ? C12 C13 1.443(12) . ? C13 H13A 0.9601 . ? C13 H13B 0.9601 . ? C13 H13C 0.9600 . ? Cu1 O2 1.968(3) . ? Cu1 O2 1.968(3) 4_565 ? Cu1 N1 1.973(4) 4_565 ? Cu1 N1 1.973(4) . ? Cu1 N2 2.392(8) . ? Cu1 U1 3.3025(8) . ? N3 O4 1.230(6) . ? N3 O5 1.248(6) . ? N3 O3 1.251(6) . ? O2 U1 2.432(3) . ? O3 U1 2.514(4) . ? O5 U1 2.530(4) . ? O6 U1 1.773(6) . ? O7 U1 1.737(5) . ? U1 O2 2.432(3) 4_565 ? U1 O3 2.514(4) 4_565 ? U1 O5 2.530(4) 4_565 ? U1 N3 2.943(4) 4_565 ? 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 C7 122.5(5) . . ? O2 C1 C2 120.0(4) . . ? C7 C1 C2 117.6(5) . . ? O1 C2 C3 124.7(5) . . ? O1 C2 C1 114.8(4) . . ? C3 C2 C1 120.4(5) . . ? C2 C3 C9 120.4(6) . . ? C2 C3 H3 119.8 . . ? C9 C3 H3 119.8 . . ? C5 C4 C5 113.4(9) 4_565 . ? C5 C4 H4A 108.9 4_565 . ? C5 C4 H4A 108.9 . . ? C5 C4 H4B 108.9 4_565 . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? N1 C5 C4 113.0(6) . . ? N1 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? N1 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? N1 C6 C7 128.9(5) . . ? N1 C6 H6 115.6 . . ? C7 C6 H6 115.6 . . ? C8 C7 C1 120.6(6) . . ? C8 C7 C6 117.1(5) . . ? C1 C7 C6 122.3(5) . . ? C9 C8 C7 120.7(6) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C3 120.4(5) . . ? C8 C9 H9 119.8 . . ? C3 C9 H9 119.8 . . ? O1 C10 C11 106.6(6) . . ? O1 C10 H10A 110.4 . . ? C11 C10 H10A 110.4 . . ? O1 C10 H10B 110.4 . . ? C11 C10 H10B 110.4 . . ? H10A C10 H10B 108.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 177.7(11) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.4 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O2 Cu1 O2 78.59(19) . 4_565 ? O2 Cu1 N1 166.19(17) . 4_565 ? O2 Cu1 N1 91.29(16) 4_565 4_565 ? O2 Cu1 N1 91.29(16) . . ? O2 Cu1 N1 166.19(17) 4_565 . ? N1 Cu1 N1 97.0(3) 4_565 . ? O2 Cu1 N2 97.62(19) . . ? O2 Cu1 N2 97.62(19) 4_565 . ? N1 Cu1 N2 93.0(2) 4_565 . ? N1 Cu1 N2 93.0(2) . . ? O2 Cu1 U1 47.01(9) . . ? O2 Cu1 U1 47.01(9) 4_565 . ? N1 Cu1 U1 119.20(14) 4_565 . ? N1 Cu1 U1 119.20(14) . . ? N2 Cu1 U1 128.1(2) . . ? C6 N1 C5 115.3(5) . . ? C6 N1 Cu1 122.7(4) . . ? C5 N1 Cu1 121.9(4) . . ? C12 N2 Cu1 163.6(8) . . ? O4 N3 O5 122.3(5) . . ? O4 N3 O3 121.1(5) . . ? O5 N3 O3 116.5(4) . . ? C2 O1 C10 116.1(5) . . ? C1 O2 Cu1 124.3(3) . . ? C1 O2 U1 135.4(3) . . ? Cu1 O2 U1 96.69(13) . . ? N3 O3 U1 97.1(3) . . ? N3 O5 U1 96.4(3) . . ? O7 U1 O6 174.2(2) . . ? O7 U1 O2 98.59(17) . 4_565 ? O6 U1 O2 86.34(18) . 4_565 ? O7 U1 O2 98.59(17) . . ? O6 U1 O2 86.34(18) . . ? O2 U1 O2 61.66(15) 4_565 . ? O7 U1 O3 92.55(10) . . ? O6 U1 O3 86.47(10) . . ? O2 U1 O3 68.53(12) 4_565 . ? O2 U1 O3 130.00(12) . . ? O7 U1 O3 92.55(10) . 4_565 ? O6 U1 O3 86.47(10) . 4_565 ? O2 U1 O3 130.00(12) 4_565 4_565 ? O2 U1 O3 68.53(12) . 4_565 ? O3 U1 O3 159.6(2) . 4_565 ? O7 U1 O5 87.24(19) . 4_565 ? O6 U1 O5 87.80(19) . 4_565 ? O2 U1 O5 174.13(12) 4_565 4_565 ? O2 U1 O5 118.33(13) . 4_565 ? O3 U1 O5 110.74(13) . 4_565 ? O3 U1 O5 49.84(13) 4_565 4_565 ? O7 U1 O5 87.24(19) . . ? O6 U1 O5 87.80(19) . . ? O2 U1 O5 118.33(13) 4_565 . ? O2 U1 O5 174.13(12) . . ? O3 U1 O5 49.84(13) . . ? O3 U1 O5 110.75(13) 4_565 . ? O5 U1 O5 61.01(18) 4_565 . ? O7 U1 N3 90.87(14) . 4_565 ? O6 U1 N3 85.85(15) . 4_565 ? O2 U1 N3 154.28(12) 4_565 4_565 ? O2 U1 N3 93.40(12) . 4_565 ? O3 U1 N3 135.21(14) . 4_565 ? O3 U1 N3 24.95(13) 4_565 4_565 ? O5 U1 N3 24.93(13) 4_565 4_565 ? O5 U1 N3 85.80(14) . 4_565 ? O7 U1 Cu1 120.20(17) . . ? O6 U1 Cu1 65.56(18) . . ? O2 U1 Cu1 36.29(7) 4_565 . ? O2 U1 Cu1 36.29(8) . . ? O3 U1 Cu1 97.23(9) . . ? O3 U1 Cu1 97.23(9) 4_565 . ? O5 U1 Cu1 140.15(10) 4_565 . ? O5 U1 Cu1 140.15(10) . . ? N3 U1 Cu1 119.04(10) 4_565 . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.40 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 3.536 _refine_diff_density_min -2.064 _refine_diff_density_rms 0.172 _database_code_depnum_ccdc_archive 'CCDC 954921' ####################################################################### # # 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_3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H51 Cu2 N9 O19 U' _chemical_formula_weight 1423.09 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' U U -9.6767 9.6646 '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 14.1950(15) _cell_length_b 14.5483(15) _cell_length_c 15.8562(16) _cell_angle_alpha 64.927(4) _cell_angle_beta 74.116(4) _cell_angle_gamma 63.150(4) _cell_volume 2632.4(5) _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 square _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.795 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 3.954 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4263 _exptl_absorpt_correction_T_max 0.4767 _exptl_absorpt_process_details SADABS _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 29615 _diffrn_reflns_av_R_equivalents 0.0451 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.05 _reflns_number_total 9218 _reflns_number_gt 7208 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0800P)^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 9218 _refine_ls_number_parameters 741 _refine_ls_number_restraints 11 _refine_ls_R_factor_all 0.0583 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_ref 0.1261 _refine_ls_wR_factor_gt 0.1099 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 0.8298(5) 0.4032(5) -0.0536(5) 0.0406(15) Uani 1 1 d . . . C2 C 0.8383(5) 0.4358(5) -0.1524(4) 0.0397(14) Uani 1 1 d . . . C3 C 0.7533(5) 0.4551(6) -0.1966(5) 0.0516(17) Uani 1 1 d . . . H3 H 0.7582 0.4781 -0.2615 0.062 Uiso 1 1 calc R . . C4 C 0.6651(6) 0.4399(6) -0.1439(5) 0.0574(19) Uani 1 1 d . . . H4 H 0.6106 0.4509 -0.1733 0.069 Uiso 1 1 calc R . . C5 C 0.6539(5) 0.4083(6) -0.0465(6) 0.0550(18) Uani 1 1 d . . . H5 H 0.5925 0.3986 -0.0118 0.066 Uiso 1 1 calc R . . C6 C 0.7334(5) 0.3916(5) -0.0023(5) 0.0440(16) Uani 1 1 d . . . C7 C 0.9288(5) 0.4527(5) -0.2110(5) 0.0434(15) Uani 1 1 d . . . H7 H 0.9283 0.4735 -0.2751 0.052 Uiso 1 1 calc R . . C8 C 1.1003(5) 0.4543(5) -0.2473(4) 0.0371(14) Uani 1 1 d . . . C9 C 1.1975(7) 0.4802(6) -0.3945(5) 0.065(2) Uani 1 1 d . . . H9 H 1.2044 0.4915 -0.4578 0.078 Uiso 1 1 calc R . . C10 C 1.2798(7) 0.4700(8) -0.3552(6) 0.084(3) Uani 1 1 d . . . H10 H 1.3413 0.4752 -0.3933 0.101 Uiso 1 1 calc R . . C11 C 1.2734(5) 0.4528(6) -0.2637(5) 0.0538(18) Uani 1 1 d . . . H11 H 1.3283 0.4483 -0.2389 0.065 Uiso 1 1 calc R . . C12 C 1.1845(5) 0.4424(5) -0.2090(5) 0.0475(16) Uani 1 1 d . . . C13 C 1.2468(5) 0.3934(5) -0.0652(5) 0.0434(15) Uani 1 1 d . . . H13 H 1.3088 0.4013 -0.1002 0.052 Uiso 1 1 calc R . . C14 C 1.1548(5) 0.3444(5) 0.0955(5) 0.0410(15) Uani 1 1 d . . . C15 C 1.2427(5) 0.3568(5) 0.0340(5) 0.0393(14) Uani 1 1 d . . . C16 C 1.3367(5) 0.3312(6) 0.0711(6) 0.0563(19) Uani 1 1 d . . . H16 H 1.3954 0.3406 0.0302 0.068 Uiso 1 1 calc R . . C17 C 1.3416(6) 0.2945(6) 0.1630(5) 0.0556(19) Uani 1 1 d . . . H17 H 1.4033 0.2789 0.1853 0.067 Uiso 1 1 calc R . . C18 C 1.2537(6) 0.2790(5) 0.2268(5) 0.057(2) Uani 1 1 d . . . H18 H 1.2572 0.2539 0.2908 0.068 Uiso 1 1 calc R . . C19 C 1.1621(5) 0.3015(5) 0.1931(5) 0.0439(15) Uani 1 1 d . . . C20 C 0.6345(6) 0.3611(6) 0.1482(5) 0.062(2) Uani 1 1 d . . . H20A H 0.6182 0.3036 0.1472 0.075 Uiso 1 1 calc R . . H20B H 0.5766 0.4311 0.1246 0.075 Uiso 1 1 calc R . . C21 C 0.6487(7) 0.3399(8) 0.2458(6) 0.081(3) Uani 1 1 d . . . H21A H 0.7061 0.2705 0.2683 0.122 Uiso 1 1 calc R . . H21B H 0.5845 0.3383 0.2857 0.122 Uiso 1 1 calc R . . H21C H 0.6646 0.3974 0.2459 0.122 Uiso 1 1 calc R . . C22 C 1.0737(7) 0.2460(6) 0.3468(5) 0.064(2) Uani 1 1 d . . . H22A H 1.0722 0.2996 0.3688 0.076 Uiso 1 1 calc R . . H22B H 1.1372 0.1802 0.3652 0.076 Uiso 1 1 calc R . . C23 C 0.9758(8) 0.2189(8) 0.3886(6) 0.086(3) Uani 1 1 d . . . H23A H 0.9135 0.2856 0.3756 0.129 Uiso 1 1 calc R . . H23B H 0.9773 0.1825 0.4551 0.129 Uiso 1 1 calc R . . H23C H 0.9746 0.1716 0.3616 0.129 Uiso 1 1 calc R . . C24 C -0.1884(4) 0.0950(5) 0.0756(4) 0.0381(14) Uani 1 1 d . . . C25 C -0.2375(5) 0.0687(5) 0.1683(5) 0.0449(16) Uani 1 1 d . . . C26 C -0.3398(5) 0.0738(5) 0.1866(5) 0.0493(16) Uani 1 1 d . . . H26 H -0.3704 0.0556 0.2482 0.059 Uiso 1 1 calc R . . C27 C -0.3980(5) 0.1057(6) 0.1145(6) 0.0526(18) Uani 1 1 d . . . H27 H -0.4671 0.1084 0.1279 0.063 Uiso 1 1 calc R . . C28 C -0.3539(5) 0.1328(5) 0.0245(5) 0.0481(17) Uani 1 1 d . . . H28 H -0.3939 0.1544 -0.0232 0.058 Uiso 1 1 calc R . . C29 C -0.2487(4) 0.1293(5) 0.0010(5) 0.0391(14) Uani 1 1 d . . . C30 C -0.2103(5) 0.1616(5) -0.0950(5) 0.0437(15) Uani 1 1 d . . . H30 H -0.2547 0.1798 -0.1380 0.052 Uiso 1 1 calc R . . C31 C -0.0902(5) 0.2091(5) -0.2247(4) 0.0411(15) Uani 1 1 d . . . C32 C -0.1188(7) 0.2801(7) -0.3812(5) 0.070(2) Uani 1 1 d . . . H32 H -0.1596 0.2986 -0.4273 0.084 Uiso 1 1 calc R . . C33 C -0.0278(7) 0.2980(7) -0.4079(5) 0.068(2) Uani 1 1 d . . . H33 H -0.0086 0.3313 -0.4708 0.082 Uiso 1 1 calc R . . C34 C 0.0356(6) 0.2672(6) -0.3421(5) 0.0513(17) Uani 1 1 d . . . H34 H 0.0993 0.2775 -0.3597 0.062 Uiso 1 1 calc R . . C35 C 0.0054(5) 0.2219(5) -0.2519(4) 0.0443(15) Uani 1 1 d . . . C36 C 0.1576(5) 0.1908(5) -0.1939(5) 0.0421(15) Uani 1 1 d . . . H36 H 0.1854 0.2137 -0.2560 0.051 Uiso 1 1 calc R . . C37 C 0.1893(5) 0.1234(5) -0.0262(5) 0.0428(15) Uani 1 1 d . . . C38 C 0.2209(5) 0.1605(5) -0.1230(5) 0.0449(15) Uani 1 1 d . . . C39 C 0.3225(5) 0.1690(6) -0.1551(6) 0.0568(18) Uani 1 1 d . . . H39 H 0.3440 0.1919 -0.2189 0.068 Uiso 1 1 calc R . . C40 C 0.3875(5) 0.1438(6) -0.0928(6) 0.060(2) Uani 1 1 d . . . H40 H 0.4524 0.1514 -0.1143 0.072 Uiso 1 1 calc R . . C41 C 0.3579(5) 0.1070(6) 0.0015(6) 0.0542(18) Uani 1 1 d . . . H41 H 0.4038 0.0895 0.0430 0.065 Uiso 1 1 calc R . . C42 C 0.2607(5) 0.0951(5) 0.0372(5) 0.0479(16) Uani 1 1 d . . . C43 C -0.2172(6) 0.0096(7) 0.3304(5) 0.0602(19) Uani 1 1 d . . . H43A H -0.2269 -0.0588 0.3507 0.072 Uiso 1 1 calc R . . H43B H -0.2854 0.0666 0.3387 0.072 Uiso 1 1 calc R . . C44 C -0.1400(7) -0.0030(8) 0.3863(5) 0.079(3) Uani 1 1 d . . . H44A H -0.0729 -0.0599 0.3779 0.119 Uiso 1 1 calc R . . H44B H -0.1665 -0.0223 0.4514 0.119 Uiso 1 1 calc R . . H44C H -0.1309 0.0651 0.3656 0.119 Uiso 1 1 calc R . . C45 C 0.2945(7) 0.0175(7) 0.1976(6) 0.073(3) Uani 1 1 d . . . H45A H 0.3119 0.0767 0.1935 0.088 Uiso 1 1 calc R . . H45B H 0.3599 -0.0416 0.1874 0.088 Uiso 1 1 calc R . . C46 C 0.2383(8) -0.0231(10) 0.2922(7) 0.110(4) Uani 1 1 d . . . H46A H 0.1681 0.0313 0.2970 0.165 Uiso 1 1 calc R . . H46B H 0.2771 -0.0365 0.3399 0.165 Uiso 1 1 calc R . . H46C H 0.2336 -0.0902 0.3000 0.165 Uiso 1 1 calc R . . C47 C 0.5615(8) 0.3567(8) 0.7163(9) 0.086(3) Uani 1 1 d . . . C48 C 0.5800(10) 0.4328(10) 0.6312(8) 0.120(4) Uani 1 1 d . . . H48A H 0.5966 0.4839 0.6418 0.181 Uiso 1 1 calc R . . H48B H 0.5178 0.4718 0.5984 0.181 Uiso 1 1 calc R . . H48C H 0.6386 0.3954 0.5945 0.181 Uiso 1 1 calc R . . Cu1 Cu 1.03370(5) 0.40569(6) -0.05514(5) 0.03709(18) Uani 1 1 d . . . Cu2 Cu -0.00939(5) 0.13432(6) -0.05510(5) 0.03645(18) Uani 1 1 d . . . N1 N 1.0124(4) 0.4413(4) -0.1826(3) 0.0394(12) Uani 1 1 d . . . N2 N 1.1071(5) 0.4736(5) -0.3397(4) 0.0646(17) Uani 1 1 d . . . N3 N 1.1703(4) 0.4167(4) -0.1108(3) 0.0412(12) Uani 1 1 d . . . N4 N -0.1182(4) 0.1678(4) -0.1277(3) 0.0386(12) Uani 1 1 d . . . N5 N -0.1536(5) 0.2358(6) -0.2896(4) 0.0681(18) Uani 1 1 d . . . N6 N 0.0648(4) 0.1884(4) -0.1774(4) 0.0425(12) Uani 1 1 d . . . N8 N 0.2412(5) 0.3305(5) 0.4526(4) 0.0585(16) Uani 1 1 d . . . N9 N 0.5487(8) 0.2998(10) 0.7852(9) 0.151(5) Uani 1 1 d . . . O2 O 0.9029(3) 0.3851(3) -0.0061(3) 0.0396(10) Uani 1 1 d . . . O3 O 1.0614(3) 0.3709(4) 0.0688(3) 0.0452(11) Uani 1 1 d . . . O1 O 0.7317(3) 0.3626(4) 0.0917(3) 0.0548(12) Uani 1 1 d . . . O4 O 1.0738(4) 0.2895(4) 0.2475(3) 0.0533(12) Uani 1 1 d . . . O7 O -0.0879(3) 0.0823(3) 0.0621(3) 0.0383(9) Uani 1 1 d . . . O8 O 0.0979(3) 0.1146(3) 0.0099(3) 0.0405(10) Uani 1 1 d . . . O6 O -0.1744(3) 0.0386(4) 0.2339(3) 0.0477(11) Uani 1 1 d . . . O9 O 0.2248(4) 0.0563(5) 0.1287(4) 0.0640(14) Uani 1 1 d . . . O18 O 0.4895(4) 0.1903(4) 0.3666(3) 0.0589(13) Uani 1 1 d . . . O17 O 0.4234(5) 0.1261(5) 0.6081(3) 0.0684(15) Uani 1 1 d . . . O19 O 0.4071(4) 0.0210(4) 0.4884(4) 0.0571(13) Uani 1 1 d D . . O14 O 0.6363(4) 0.1430(4) 0.5005(4) 0.0695(15) Uani 1 1 d . . . O15 O 0.5115(5) 0.3003(4) 0.4870(4) 0.0724(15) Uani 1 1 d . . . O12 O 0.3190(4) 0.3494(4) 0.4532(4) 0.0686(14) Uani 1 1 d . . . O13 O 0.1547(4) 0.4022(5) 0.4368(4) 0.0755(16) Uani 1 1 d . . . O11 O 0.2615(4) 0.2299(4) 0.4678(4) 0.0611(13) Uani 1 1 d . . . O5 O 0.9182(4) 0.2784(5) 0.1800(4) 0.0628(13) Uani 1 1 d D . . O10 O 1.0076(4) 0.0880(5) 0.1868(4) 0.0598(13) Uani 1 1 d D . . U1 U 0.45830(2) 0.15377(2) 0.487760(16) 0.04617(11) Uani 1 1 d D . . N7 N 0.6082(6) 0.2417(6) 0.4949(5) 0.0666(18) Uani 1 1 d . . . O16 O 0.6710(5) 0.2767(6) 0.4949(6) 0.104(2) Uani 1 1 d . . . H19C H 0.415(7) 0.037(5) 0.4289(17) 0.16(6) Uiso 1 1 d D . . H19D H 0.3413(17) 0.057(3) 0.486(6) 0.08(3) Uiso 1 1 d D . . H10A H 0.984(6) 0.052(6) 0.175(8) 0.12(4) Uiso 1 1 d D . . H10B H 0.964(5) 0.153(3) 0.183(6) 0.08(3) Uiso 1 1 d D . . H5B H 0.981(3) 0.269(8) 0.181(6) 0.13(4) Uiso 1 1 d D . . H5A H 0.893(5) 0.326(5) 0.130(3) 0.08(3) 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 0.038(3) 0.034(3) 0.054(4) -0.019(3) -0.010(3) -0.011(3) C2 0.044(4) 0.033(3) 0.040(4) -0.016(3) -0.008(3) -0.008(3) C3 0.049(4) 0.056(4) 0.058(4) -0.026(4) -0.018(3) -0.014(3) C4 0.049(4) 0.062(5) 0.069(5) -0.027(4) -0.018(4) -0.017(4) C5 0.041(4) 0.052(4) 0.080(6) -0.032(4) -0.006(4) -0.017(3) C6 0.036(3) 0.037(3) 0.060(4) -0.025(3) -0.008(3) -0.006(3) C7 0.046(4) 0.037(3) 0.046(4) -0.017(3) -0.010(3) -0.009(3) C8 0.043(3) 0.028(3) 0.032(3) -0.009(2) 0.001(3) -0.010(3) C9 0.080(6) 0.063(5) 0.038(4) -0.012(4) 0.004(4) -0.027(4) C10 0.056(5) 0.104(7) 0.062(6) -0.015(5) 0.013(4) -0.030(5) C11 0.045(4) 0.062(4) 0.049(4) -0.010(3) 0.001(3) -0.027(3) C12 0.043(4) 0.042(4) 0.053(4) -0.017(3) -0.001(3) -0.015(3) C13 0.034(3) 0.035(3) 0.067(5) -0.025(3) -0.001(3) -0.014(3) C14 0.039(3) 0.035(3) 0.055(4) -0.025(3) -0.015(3) -0.005(3) C15 0.040(3) 0.030(3) 0.054(4) -0.021(3) -0.013(3) -0.008(3) C16 0.039(4) 0.053(4) 0.080(6) -0.033(4) -0.011(4) -0.008(3) C17 0.043(4) 0.055(4) 0.071(5) -0.029(4) -0.025(4) -0.004(3) C18 0.061(5) 0.046(4) 0.065(5) -0.027(4) -0.033(4) 0.000(3) C19 0.049(4) 0.037(3) 0.051(4) -0.022(3) -0.011(3) -0.011(3) C20 0.048(4) 0.059(5) 0.067(5) -0.017(4) 0.012(4) -0.025(4) C21 0.074(6) 0.093(7) 0.061(5) -0.015(5) 0.023(4) -0.049(5) C22 0.096(6) 0.057(5) 0.044(4) -0.016(3) -0.026(4) -0.025(4) C23 0.096(7) 0.110(8) 0.056(5) -0.029(5) -0.002(5) -0.047(6) C24 0.027(3) 0.034(3) 0.046(4) -0.015(3) 0.006(3) -0.010(2) C25 0.040(4) 0.037(3) 0.044(4) -0.012(3) 0.005(3) -0.010(3) C26 0.040(4) 0.049(4) 0.052(4) -0.022(3) 0.013(3) -0.017(3) C27 0.026(3) 0.050(4) 0.085(6) -0.034(4) 0.006(3) -0.015(3) C28 0.032(3) 0.040(4) 0.070(5) -0.023(3) -0.012(3) -0.005(3) C29 0.032(3) 0.025(3) 0.060(4) -0.017(3) -0.005(3) -0.009(2) C30 0.040(4) 0.040(4) 0.047(4) -0.014(3) -0.013(3) -0.008(3) C31 0.048(4) 0.029(3) 0.041(4) -0.012(3) -0.005(3) -0.011(3) C32 0.065(5) 0.091(6) 0.039(4) -0.020(4) -0.006(4) -0.019(5) C33 0.081(6) 0.071(5) 0.036(4) -0.013(4) 0.007(4) -0.027(4) C34 0.055(4) 0.055(4) 0.043(4) -0.016(3) 0.007(3) -0.027(3) C35 0.047(4) 0.038(3) 0.043(4) -0.014(3) -0.002(3) -0.013(3) C36 0.049(4) 0.029(3) 0.047(4) -0.012(3) 0.007(3) -0.022(3) C37 0.036(3) 0.033(3) 0.061(4) -0.022(3) -0.006(3) -0.009(3) C38 0.033(3) 0.040(4) 0.058(4) -0.020(3) 0.008(3) -0.015(3) C39 0.048(4) 0.051(4) 0.072(5) -0.026(4) 0.014(4) -0.027(3) C40 0.039(4) 0.054(4) 0.104(7) -0.041(5) 0.004(4) -0.025(3) C41 0.043(4) 0.050(4) 0.077(5) -0.029(4) -0.010(4) -0.016(3) C42 0.037(4) 0.044(4) 0.068(5) -0.026(3) -0.007(3) -0.013(3) C43 0.060(4) 0.067(5) 0.044(4) -0.020(4) 0.012(3) -0.026(4) C44 0.081(6) 0.108(7) 0.029(4) -0.015(4) 0.003(4) -0.033(5) C45 0.066(5) 0.072(5) 0.094(7) -0.038(5) -0.041(5) -0.009(4) C46 0.111(8) 0.127(9) 0.071(7) -0.026(6) -0.045(6) -0.016(7) C47 0.078(6) 0.070(6) 0.109(8) -0.009(6) -0.029(6) -0.038(5) C48 0.130(10) 0.106(9) 0.098(9) -0.030(7) -0.005(7) -0.032(8) Cu1 0.0341(4) 0.0392(4) 0.0374(4) -0.0156(3) -0.0037(3) -0.0115(3) Cu2 0.0315(4) 0.0358(4) 0.0358(4) -0.0086(3) -0.0027(3) -0.0119(3) N1 0.045(3) 0.034(3) 0.039(3) -0.015(2) -0.004(2) -0.013(2) N2 0.081(5) 0.058(4) 0.053(4) -0.017(3) -0.006(3) -0.029(3) N3 0.045(3) 0.041(3) 0.036(3) -0.016(2) 0.000(2) -0.015(2) N4 0.033(3) 0.035(3) 0.038(3) -0.009(2) -0.007(2) -0.007(2) N5 0.055(4) 0.077(4) 0.054(4) -0.023(3) -0.008(3) -0.008(3) N6 0.038(3) 0.035(3) 0.045(3) -0.011(2) -0.001(2) -0.011(2) N8 0.059(4) 0.059(4) 0.047(4) -0.016(3) -0.002(3) -0.019(4) N9 0.120(8) 0.151(10) 0.160(10) 0.043(8) -0.065(8) -0.096(8) O2 0.037(2) 0.045(2) 0.036(2) -0.0124(19) -0.0045(18) -0.0167(19) O3 0.036(2) 0.057(3) 0.041(2) -0.016(2) -0.0066(19) -0.016(2) O1 0.041(3) 0.068(3) 0.052(3) -0.019(2) 0.003(2) -0.025(2) O4 0.060(3) 0.060(3) 0.043(3) -0.017(2) -0.014(2) -0.022(2) O7 0.033(2) 0.043(2) 0.042(2) -0.0140(19) -0.0024(18) -0.0184(18) O8 0.028(2) 0.047(2) 0.043(2) -0.015(2) -0.0016(18) -0.0148(18) O6 0.044(2) 0.056(3) 0.043(3) -0.019(2) 0.006(2) -0.024(2) O9 0.046(3) 0.088(4) 0.064(3) -0.030(3) -0.018(2) -0.020(3) O18 0.062(3) 0.070(3) 0.036(3) -0.012(2) 0.004(2) -0.030(3) O17 0.093(4) 0.078(4) 0.033(3) -0.015(2) 0.006(3) -0.043(3) O19 0.057(3) 0.041(3) 0.081(4) -0.023(3) -0.011(3) -0.021(2) O14 0.076(4) 0.062(3) 0.083(4) -0.026(3) -0.017(3) -0.032(3) O15 0.082(4) 0.053(3) 0.083(4) -0.024(3) -0.009(3) -0.027(3) O12 0.068(3) 0.057(3) 0.084(4) -0.032(3) 0.001(3) -0.025(3) O13 0.065(4) 0.066(4) 0.067(4) -0.013(3) -0.010(3) -0.009(3) O11 0.070(3) 0.050(3) 0.062(3) -0.016(2) -0.009(3) -0.024(3) O5 0.060(3) 0.084(4) 0.050(3) -0.023(3) -0.007(3) -0.031(3) O10 0.060(3) 0.060(4) 0.064(3) -0.014(3) -0.013(3) -0.031(3) U1 0.05595(18) 0.04436(17) 0.03858(16) -0.01357(11) 0.00236(11) -0.02452(13) N7 0.091(5) 0.061(4) 0.064(4) -0.019(3) -0.012(4) -0.044(4) O16 0.109(5) 0.094(5) 0.153(7) -0.052(5) -0.020(5) -0.063(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 C1 O2 1.315(7) . ? C1 C2 1.418(9) . ? C1 C6 1.430(9) . ? C2 C7 1.418(9) . ? C2 C3 1.420(8) . ? C3 C4 1.355(10) . ? C3 H3 0.9300 . ? C4 C5 1.397(10) . ? C4 H4 0.9300 . ? C5 C6 1.365(9) . ? C5 H5 0.9300 . ? C6 O1 1.362(8) . ? C7 N1 1.301(8) . ? C7 H7 0.9300 . ? C8 N2 1.354(8) . ? C8 C12 1.395(9) . ? C8 N1 1.411(8) . ? C9 N2 1.358(10) . ? C9 C10 1.393(12) . ? C9 H9 0.9300 . ? C10 C11 1.348(11) . ? C10 H10 0.9300 . ? C11 C12 1.353(9) . ? C11 H11 0.9300 . ? C12 N3 1.417(8) . ? C13 N3 1.307(8) . ? C13 C15 1.424(9) . ? C13 H13 0.9300 . ? C14 O3 1.339(7) . ? C14 C15 1.389(9) . ? C14 C19 1.417(9) . ? C15 C16 1.436(9) . ? C16 C17 1.332(10) . ? C16 H16 0.9300 . ? C17 C18 1.415(10) . ? C17 H17 0.9300 . ? C18 C19 1.390(9) . ? C18 H18 0.9300 . ? C19 O4 1.350(8) . ? C20 O1 1.429(8) . ? C20 C21 1.497(11) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 O4 1.427(8) . ? C22 C23 1.515(11) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 O7 1.321(7) . ? C24 C25 1.413(9) . ? C24 C29 1.431(8) . ? C25 O6 1.358(8) . ? C25 C26 1.374(9) . ? C26 C27 1.387(10) . ? C26 H26 0.9300 . ? C27 C28 1.357(10) . ? C27 H27 0.9300 . ? C28 C29 1.419(9) . ? C28 H28 0.9300 . ? C29 C30 1.415(9) . ? C30 N4 1.297(8) . ? C30 H30 0.9300 . ? C31 N5 1.368(8) . ? C31 C35 1.379(9) . ? C31 N4 1.408(8) . ? C32 C33 1.353(12) . ? C32 N5 1.367(10) . ? C32 H32 0.9300 . ? C33 C34 1.361(10) . ? C33 H33 0.9300 . ? C34 C35 1.335(9) . ? C34 H34 0.9300 . ? C35 N6 1.426(8) . ? C36 N6 1.284(8) . ? C36 C38 1.428(9) . ? C36 H36 0.9300 . ? C37 O8 1.306(7) . ? C37 C38 1.410(9) . ? C37 C42 1.427(9) . ? C38 C39 1.436(9) . ? C39 C40 1.359(10) . ? C39 H39 0.9300 . ? C40 C41 1.371(10) . ? C40 H40 0.9300 . ? C41 C42 1.400(9) . ? C41 H41 0.9300 . ? C42 O9 1.359(9) . ? C43 O6 1.437(8) . ? C43 C44 1.495(10) . ? C43 H43A 0.9700 . ? C43 H43B 0.9700 . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 O9 1.434(8) . ? C45 C46 1.502(14) . ? C45 H45A 0.9700 . ? C45 H45B 0.9700 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 N9 1.082(13) . ? C47 C48 1.384(14) . ? C48 H48A 0.9600 . ? C48 H48B 0.9600 . ? C48 H48C 0.9600 . ? Cu1 O2 1.911(4) . ? Cu1 O3 1.916(4) . ? Cu1 N1 1.937(5) . ? Cu1 N3 1.947(5) . ? Cu2 O8 1.918(4) . ? Cu2 O7 1.924(4) . ? Cu2 N4 1.941(5) . ? Cu2 N6 1.956(5) . ? N8 O13 1.203(7) . ? N8 O12 1.255(8) . ? N8 O11 1.281(8) . ? O18 U1 1.746(5) . ? O17 U1 1.749(5) . ? O19 U1 2.334(5) 2_656 ? O19 U1 2.346(4) . ? O19 H19C 0.86(2) . ? O19 H19D 0.84(2) . ? O14 N7 1.273(8) . ? O14 U1 2.520(5) . ? O15 N7 1.255(8) . ? O15 U1 2.558(5) . ? O12 U1 2.549(5) . ? O11 U1 2.554(5) . ? O5 H5B 0.84(2) . ? O5 H5A 0.84(2) . ? O10 H10A 0.83(2) . ? O10 H10B 0.84(2) . ? U1 O19 2.334(5) 2_656 ? U1 U1 3.9453(7) 2_656 ? U1 H19C 2.60(2) . ? N7 O16 1.210(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 C2 124.8(6) . . ? O2 C1 C6 117.7(6) . . ? C2 C1 C6 117.5(5) . . ? C1 C2 C7 122.7(5) . . ? C1 C2 C3 120.0(6) . . ? C7 C2 C3 117.3(6) . . ? C4 C3 C2 119.7(7) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 121.7(6) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C6 C5 C4 119.8(7) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? O1 C6 C5 125.7(6) . . ? O1 C6 C1 113.1(5) . . ? C5 C6 C1 121.2(6) . . ? N1 C7 C2 125.4(6) . . ? N1 C7 H7 117.3 . . ? C2 C7 H7 117.3 . . ? N2 C8 C12 120.6(6) . . ? N2 C8 N1 124.3(6) . . ? C12 C8 N1 115.1(5) . . ? N2 C9 C10 119.4(7) . . ? N2 C9 H9 120.3 . . ? C10 C9 H9 120.3 . . ? C11 C10 C9 122.2(7) . . ? C11 C10 H10 118.9 . . ? C9 C10 H10 118.9 . . ? C10 C11 C12 117.8(7) . . ? C10 C11 H11 121.1 . . ? C12 C11 H11 121.1 . . ? C11 C12 C8 120.9(6) . . ? C11 C12 N3 123.6(6) . . ? C8 C12 N3 115.4(6) . . ? N3 C13 C15 125.1(6) . . ? N3 C13 H13 117.5 . . ? C15 C13 H13 117.5 . . ? O3 C14 C15 124.2(6) . . ? O3 C14 C19 116.6(6) . . ? C15 C14 C19 119.2(5) . . ? C14 C15 C13 124.3(5) . . ? C14 C15 C16 119.0(6) . . ? C13 C15 C16 116.7(6) . . ? C17 C16 C15 121.4(7) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C18 120.4(6) . . ? C16 C17 H17 119.8 . . ? C18 C17 H17 119.8 . . ? C19 C18 C17 119.6(7) . . ? C19 C18 H18 120.2 . . ? C17 C18 H18 120.2 . . ? O4 C19 C18 124.5(6) . . ? O4 C19 C14 115.1(5) . . ? C18 C19 C14 120.3(7) . . ? O1 C20 C21 107.3(6) . . ? O1 C20 H20A 110.2 . . ? C21 C20 H20A 110.2 . . ? O1 C20 H20B 110.2 . . ? C21 C20 H20B 110.2 . . ? H20A C20 H20B 108.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 C23 107.6(6) . . ? O4 C22 H22A 110.2 . . ? C23 C22 H22A 110.2 . . ? O4 C22 H22B 110.2 . . ? C23 C22 H22B 110.2 . . ? H22A C22 H22B 108.5 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O7 C24 C25 118.6(5) . . ? O7 C24 C29 123.1(5) . . ? C25 C24 C29 118.3(5) . . ? O6 C25 C26 125.2(6) . . ? O6 C25 C24 113.9(5) . . ? C26 C25 C24 120.9(6) . . ? C25 C26 C27 121.0(6) . . ? C25 C26 H26 119.5 . . ? C27 C26 H26 119.5 . . ? C28 C27 C26 119.8(6) . . ? C28 C27 H27 120.1 . . ? C26 C27 H27 120.1 . . ? C27 C28 C29 122.0(6) . . ? C27 C28 H28 119.0 . . ? C29 C28 H28 119.0 . . ? C30 C29 C28 118.0(6) . . ? C30 C29 C24 124.0(5) . . ? C28 C29 C24 118.0(6) . . ? N4 C30 C29 125.3(5) . . ? N4 C30 H30 117.3 . . ? C29 C30 H30 117.3 . . ? N5 C31 C35 120.9(6) . . ? N5 C31 N4 122.5(6) . . ? C35 C31 N4 116.5(5) . . ? C33 C32 N5 122.9(7) . . ? C33 C32 H32 118.5 . . ? N5 C32 H32 118.5 . . ? C32 C33 C34 119.6(7) . . ? C32 C33 H33 120.2 . . ? C34 C33 H33 120.2 . . ? C35 C34 C33 119.2(7) . . ? C35 C34 H34 120.4 . . ? C33 C34 H34 120.4 . . ? C34 C35 C31 121.0(6) . . ? C34 C35 N6 123.8(6) . . ? C31 C35 N6 115.2(6) . . ? N6 C36 C38 124.3(6) . . ? N6 C36 H36 117.9 . . ? C38 C36 H36 117.9 . . ? O8 C37 C38 124.4(6) . . ? O8 C37 C42 117.4(6) . . ? C38 C37 C42 118.2(6) . . ? C37 C38 C36 124.0(6) . . ? C37 C38 C39 119.8(6) . . ? C36 C38 C39 116.2(6) . . ? C40 C39 C38 120.4(7) . . ? C40 C39 H39 119.8 . . ? C38 C39 H39 119.8 . . ? C39 C40 C41 120.3(7) . . ? C39 C40 H40 119.9 . . ? C41 C40 H40 119.9 . . ? C40 C41 C42 122.0(7) . . ? C40 C41 H41 119.0 . . ? C42 C41 H41 119.0 . . ? O9 C42 C41 127.0(6) . . ? O9 C42 C37 113.7(6) . . ? C41 C42 C37 119.3(7) . . ? O6 C43 C44 107.5(6) . . ? O6 C43 H43A 110.2 . . ? C44 C43 H43A 110.2 . . ? O6 C43 H43B 110.2 . . ? C44 C43 H43B 110.2 . . ? H43A C43 H43B 108.5 . . ? C43 C44 H44A 109.5 . . ? C43 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C43 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? O9 C45 C46 107.7(7) . . ? O9 C45 H45A 110.2 . . ? C46 C45 H45A 110.2 . . ? O9 C45 H45B 110.2 . . ? C46 C45 H45B 110.2 . . ? H45A C45 H45B 108.5 . . ? C45 C46 H46A 109.5 . . ? C45 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C45 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? N9 C47 C48 175.9(14) . . ? C47 C48 H48A 109.5 . . ? C47 C48 H48B 109.5 . . ? H48A C48 H48B 109.5 . . ? C47 C48 H48C 109.5 . . ? H48A C48 H48C 109.5 . . ? H48B C48 H48C 109.5 . . ? O2 Cu1 O3 90.16(17) . . ? O2 Cu1 N1 92.60(19) . . ? O3 Cu1 N1 177.2(2) . . ? O2 Cu1 N3 174.57(19) . . ? O3 Cu1 N3 93.06(19) . . ? N1 Cu1 N3 84.2(2) . . ? O8 Cu2 O7 90.60(16) . . ? O8 Cu2 N4 174.7(2) . . ? O7 Cu2 N4 92.86(19) . . ? O8 Cu2 N6 92.2(2) . . ? O7 Cu2 N6 177.18(18) . . ? N4 Cu2 N6 84.3(2) . . ? C7 N1 C8 120.2(5) . . ? C7 N1 Cu1 126.8(5) . . ? C8 N1 Cu1 113.0(4) . . ? C8 N2 C9 119.0(6) . . ? C13 N3 C12 121.5(6) . . ? C13 N3 Cu1 125.9(4) . . ? C12 N3 Cu1 112.3(4) . . ? C30 N4 C31 121.2(5) . . ? C30 N4 Cu2 126.5(4) . . ? C31 N4 Cu2 112.2(4) . . ? C32 N5 C31 116.2(7) . . ? C36 N6 C35 121.1(6) . . ? C36 N6 Cu2 127.1(5) . . ? C35 N6 Cu2 111.7(4) . . ? O13 N8 O12 122.3(7) . . ? O13 N8 O11 122.6(7) . . ? O12 N8 O11 115.0(6) . . ? C1 O2 Cu1 127.4(4) . . ? C14 O3 Cu1 126.4(4) . . ? C6 O1 C20 117.4(5) . . ? C19 O4 C22 119.3(5) . . ? C24 O7 Cu2 127.0(4) . . ? C37 O8 Cu2 127.4(4) . . ? C25 O6 C43 118.0(5) . . ? C42 O9 C45 117.8(6) . . ? U1 O19 U1 114.9(2) 2_656 . ? U1 O19 H19C 92(6) 2_656 . ? U1 O19 H19C 97.3(17) . . ? U1 O19 H19D 144(2) 2_656 . ? U1 O19 H19D 100.2(18) . . ? H19C O19 H19D 89(3) . . ? N7 O14 U1 98.3(4) . . ? N7 O15 U1 96.9(4) . . ? N8 O12 U1 98.2(4) . . ? N8 O11 U1 97.2(4) . . ? H5B O5 H5A 113(4) . . ? H10A O10 H10B 115(4) . . ? O18 U1 O17 176.3(2) . . ? O18 U1 O19 91.2(2) . 2_656 ? O17 U1 O19 92.2(2) . 2_656 ? O18 U1 O19 89.6(2) . . ? O17 U1 O19 93.1(2) . . ? O19 U1 O19 65.1(2) 2_656 . ? O18 U1 O14 88.8(2) . . ? O17 U1 O14 91.2(2) . . ? O19 U1 O14 66.05(17) 2_656 . ? O19 U1 O14 131.08(18) . . ? O18 U1 O12 85.9(2) . . ? O17 U1 O12 90.7(2) . . ? O19 U1 O12 176.41(19) 2_656 . ? O19 U1 O12 116.95(18) . . ? O14 U1 O12 111.69(18) . . ? O18 U1 O11 90.4(2) . . ? O17 U1 O11 88.4(2) . . ? O19 U1 O11 132.71(16) 2_656 . ? O19 U1 O11 67.65(17) . . ? O14 U1 O11 161.24(18) . . ? O12 U1 O11 49.57(17) . . ? O18 U1 O15 90.4(2) . . ? O17 U1 O15 86.8(2) . . ? O19 U1 O15 115.66(18) 2_656 . ? O19 U1 O15 179.23(18) . . ? O14 U1 O15 49.70(18) . . ? O12 U1 O15 62.29(19) . . ? O11 U1 O15 111.58(18) . . ? O18 U1 U1 90.49(17) . 2_656 ? O17 U1 U1 93.15(18) . 2_656 ? O19 U1 U1 32.65(11) 2_656 2_656 ? O19 U1 U1 32.46(12) . 2_656 ? O14 U1 U1 98.66(12) . 2_656 ? O12 U1 U1 149.32(13) . 2_656 ? O11 U1 U1 100.09(11) . 2_656 ? O15 U1 U1 148.31(14) . 2_656 ? O18 U1 H19C 70.6(6) . . ? O17 U1 H19C 112.1(6) . . ? O19 U1 H19C 69(2) 2_656 . ? O19 U1 H19C 19.1(5) . . ? O14 U1 H19C 129.3(19) . . ? O12 U1 H19C 112.3(19) . . ? O11 U1 H19C 68(2) . . ? O15 U1 H19C 160.9(6) . . ? U1 U1 H19C 38.9(18) 2_656 . ? O16 N7 O15 122.7(7) . . ? O16 N7 O14 122.2(8) . . ? O15 N7 O14 115.1(6) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.05 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.301 _refine_diff_density_min -0.444 _refine_diff_density_rms 0.113 _database_code_depnum_ccdc_archive 'CCDC 954922' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H19 Cu N5 O18 U2' _chemical_formula_weight 1132.98 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' H H 0.0000 0.0000 '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' U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.6991(17) _cell_length_b 16.299(2) _cell_length_c 23.209(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.525(5) _cell_angle_gamma 90.00 _cell_volume 5524.4(12) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4193 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.02 _exptl_crystal_description square _exptl_crystal_colour red _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.724 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4152 _exptl_absorpt_coefficient_mu 12.553 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1388 _exptl_absorpt_correction_T_max 0.1688 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 31606 _diffrn_reflns_av_R_equivalents 0.1019 _diffrn_reflns_av_sigmaI/netI 0.0813 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 26.10 _reflns_number_total 5445 _reflns_number_gt 3548 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0500P)^2^+0.8689P] 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 5445 _refine_ls_number_parameters 407 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1076 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_restrained_S_all 1.011 _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 0.8688(7) 0.5561(6) 0.7677(5) 0.036(3) Uani 1 1 d . . . C2 C 0.8706(8) 0.5979(6) 0.7142(5) 0.041(3) Uani 1 1 d . . . C3 C 0.8705(9) 0.6831(7) 0.7121(7) 0.059(4) Uani 1 1 d . . . H3 H 0.8713 0.7105 0.6771 0.070 Uiso 1 1 calc R . . C4 C 0.8691(9) 0.7262(7) 0.7634(7) 0.060(4) Uani 1 1 d . . . H4 H 0.8698 0.7832 0.7625 0.073 Uiso 1 1 calc R . . C5 C 0.8669(9) 0.6875(7) 0.8145(7) 0.057(4) Uani 1 1 d . . . H5 H 0.8659 0.7179 0.8483 0.069 Uiso 1 1 calc R . . C6 C 0.8662(9) 0.6019(6) 0.8168(6) 0.047(3) Uani 1 1 d . . . C7 C 0.8647(9) 0.5634(8) 0.8736(6) 0.056(4) Uani 1 1 d . . . H7 H 0.8592 0.5984 0.9046 0.067 Uiso 1 1 calc R . . C8 C 0.8795(11) 0.4555(8) 0.9448(6) 0.069(4) Uani 1 1 d . . . H8A H 0.8502 0.4926 0.9697 0.082 Uiso 1 1 calc R . . H8B H 0.9439 0.4516 0.9595 0.082 Uiso 1 1 calc R . . C9 C 0.8364(10) 0.3732(8) 0.9456(5) 0.059(4) Uani 1 1 d . . . H9A H 0.7711 0.3786 0.9476 0.071 Uiso 1 1 calc R . . H9B H 0.8628 0.3425 0.9792 0.071 Uiso 1 1 calc R . . C10 C 0.8546(8) 0.2523(8) 0.8898(5) 0.049(3) Uani 1 1 d . . . H10 H 0.8486 0.2239 0.9239 0.059 Uiso 1 1 calc R . . C11 C 0.8643(7) 0.2378(6) 0.7816(5) 0.035(3) Uani 1 1 d . . . C12 C 0.8653(7) 0.2046(6) 0.8377(5) 0.040(3) Uani 1 1 d . . . C13 C 0.8714(9) 0.1178(7) 0.8426(6) 0.054(4) Uani 1 1 d . . . H13 H 0.8715 0.0939 0.8790 0.064 Uiso 1 1 calc R . . C14 C 0.8770(9) 0.0698(7) 0.7971(6) 0.053(4) Uani 1 1 d . . . H14 H 0.8833 0.0134 0.8020 0.063 Uiso 1 1 calc R . . C15 C 0.8735(8) 0.1037(6) 0.7424(6) 0.046(3) Uani 1 1 d . . . H15 H 0.8744 0.0694 0.7105 0.055 Uiso 1 1 calc R . . C16 C 0.8688(8) 0.1860(6) 0.7345(5) 0.042(3) Uani 1 1 d . . . C17 C 0.8939(11) 0.5864(8) 0.6149(6) 0.071(4) Uani 1 1 d . . . H17A H 0.9232 0.5473 0.5921 0.106 Uiso 1 1 calc R . . H17B H 0.9347 0.6315 0.6248 0.106 Uiso 1 1 calc R . . H17C H 0.8390 0.6062 0.5929 0.106 Uiso 1 1 calc R . . C18 C 0.8852(9) 0.1790(8) 0.6339(6) 0.061(4) Uani 1 1 d . . . H18A H 0.8335 0.1454 0.6206 0.091 Uiso 1 1 calc R . . H18B H 0.9370 0.1447 0.6459 0.091 Uiso 1 1 calc R . . H18C H 0.8994 0.2143 0.6030 0.091 Uiso 1 1 calc R . . Cu1 Cu 0.86552(10) 0.40258(7) 0.82862(6) 0.0390(4) Uani 1 1 d . . . N1 N 0.8701(7) 0.4877(6) 0.8850(4) 0.046(3) Uani 1 1 d . . . N2 N 0.8531(6) 0.3294(6) 0.8914(4) 0.044(3) Uani 1 1 d . . . N3 N 0.7684(7) 0.3770(7) 0.5565(5) 0.053(3) Uani 1 1 d . . . N4 N 0.6331(7) 0.4083(6) 0.8529(5) 0.046(3) Uani 1 1 d . . . N5 N 0.4724(7) 0.2330(6) 0.9831(5) 0.047(3) Uani 1 1 d . . . O1 O 0.8712(5) 0.5476(4) 0.6669(3) 0.042(2) Uani 1 1 d . . . O2 O 0.8700(5) 0.4732(4) 0.7632(3) 0.0363(18) Uani 1 1 d . . . O3 O 0.8607(5) 0.3197(4) 0.7704(3) 0.0368(18) Uani 1 1 d . . . O4 O 0.8639(5) 0.2284(4) 0.6825(3) 0.043(2) Uani 1 1 d . . . O5 O 0.7269(5) 0.3955(4) 0.6887(3) 0.0394(19) Uani 1 1 d . . . O6 O 0.9564(5) 0.3827(4) 0.6650(3) 0.046(2) Uani 1 1 d . . . O7 O 0.7985(6) 0.4432(5) 0.5798(3) 0.056(2) Uani 1 1 d . . . O8 O 0.7363(7) 0.3737(6) 0.5055(4) 0.070(3) Uani 1 1 d . . . O9 O 0.7770(6) 0.3143(5) 0.5886(4) 0.054(2) Uani 1 1 d . . . O10 O 0.4274(6) 0.4175(5) 0.9095(3) 0.052(2) Uani 1 1 d . . . O11 O 0.6305(5) 0.3873(4) 0.9996(3) 0.046(2) Uani 1 1 d . . . O12 O 0.4509(6) 0.4544(4) 1.0304(4) 0.043(2) Uani 1 1 d D . . O13 O 0.4593(6) 0.2930(5) 1.0135(4) 0.058(2) Uani 1 1 d . . . O14 O 0.4509(6) 0.1637(5) 0.9947(4) 0.065(3) Uani 1 1 d . . . O15 O 0.5121(7) 0.2497(5) 0.9383(4) 0.066(3) Uani 1 1 d . . . O16 O 0.6056(13) 0.4705(9) 0.8772(8) 0.039(4) Uani 0.62 1 d P . . O17 O 0.6029(6) 0.3419(5) 0.8731(4) 0.059(3) Uani 1 1 d . . . O18 O 0.6781(6) 0.4086(5) 0.8114(4) 0.061(3) Uani 1 1 d . . . U1 U 0.84152(3) 0.38815(2) 0.678654(18) 0.03216(14) Uani 1 1 d . . . U2 U 0.52737(3) 0.40441(2) 0.955269(19) 0.03463(14) Uani 1 1 d D . . O16A O 0.637(2) 0.4747(19) 0.8870(15) 0.032(9) Uiso 0.38 1 d P . . H12H H 0.489(2) 0.464(6) 1.0562(18) 0.04(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 0.028(7) 0.046(6) 0.033(7) -0.001(5) -0.003(5) 0.004(5) C2 0.044(7) 0.034(6) 0.044(8) -0.007(5) -0.002(6) 0.003(5) C3 0.058(9) 0.038(6) 0.077(11) 0.008(7) -0.005(8) -0.003(6) C4 0.055(9) 0.038(7) 0.086(12) -0.007(8) -0.003(8) -0.004(6) C5 0.057(9) 0.047(7) 0.064(11) -0.022(7) -0.009(8) 0.004(6) C6 0.054(8) 0.041(6) 0.045(9) -0.016(6) -0.001(6) 0.002(5) C7 0.057(9) 0.066(8) 0.042(9) -0.030(7) -0.005(7) 0.016(7) C8 0.093(12) 0.073(9) 0.040(9) -0.022(7) 0.010(8) 0.008(8) C9 0.067(10) 0.080(9) 0.029(8) 0.006(7) 0.004(7) 0.015(7) C10 0.056(9) 0.063(8) 0.026(8) 0.021(6) -0.008(6) -0.016(6) C11 0.042(7) 0.033(5) 0.030(7) 0.017(5) 0.000(5) 0.003(5) C12 0.035(7) 0.046(6) 0.037(8) 0.011(6) 0.000(6) -0.005(5) C13 0.051(8) 0.050(7) 0.057(9) 0.018(7) -0.003(7) -0.011(6) C14 0.070(10) 0.028(6) 0.056(9) 0.005(6) -0.011(7) -0.007(6) C15 0.042(7) 0.035(6) 0.060(9) -0.003(6) -0.001(6) -0.001(5) C16 0.052(8) 0.045(6) 0.029(7) 0.000(6) 0.006(6) 0.002(5) C17 0.078(11) 0.072(9) 0.065(11) 0.027(8) 0.021(9) -0.013(8) C18 0.060(9) 0.063(8) 0.059(10) -0.022(7) 0.011(8) 0.008(7) Cu1 0.0521(9) 0.0401(7) 0.0251(8) 0.0002(6) 0.0054(7) 0.0028(6) N1 0.059(7) 0.044(6) 0.034(7) -0.005(4) 0.000(5) 0.002(5) N2 0.047(6) 0.054(6) 0.032(6) 0.008(5) 0.005(5) 0.002(5) N3 0.045(7) 0.072(7) 0.043(8) -0.007(6) 0.003(6) 0.009(6) N4 0.045(7) 0.051(6) 0.044(7) 0.002(5) 0.009(6) 0.004(5) N5 0.060(7) 0.042(6) 0.039(7) -0.006(5) 0.000(6) 0.001(5) O1 0.060(6) 0.039(4) 0.024(5) 0.011(3) 0.000(4) -0.004(4) O2 0.058(5) 0.027(3) 0.023(4) 0.001(3) 0.003(4) -0.003(3) O3 0.049(5) 0.035(4) 0.028(5) 0.007(3) 0.008(4) 0.003(3) O4 0.051(5) 0.045(4) 0.033(5) -0.003(4) 0.007(4) 0.001(4) O5 0.036(5) 0.055(4) 0.028(5) 0.002(3) 0.005(4) 0.005(3) O6 0.045(5) 0.058(5) 0.036(5) -0.003(4) 0.003(4) -0.004(4) O7 0.080(7) 0.061(5) 0.025(5) 0.015(4) -0.007(5) -0.006(5) O8 0.071(7) 0.105(7) 0.031(6) -0.009(5) -0.011(5) 0.010(5) O9 0.060(6) 0.057(5) 0.043(6) -0.009(4) -0.007(5) 0.003(4) O10 0.050(6) 0.071(5) 0.035(5) 0.001(4) 0.002(4) 0.001(4) O11 0.047(5) 0.056(5) 0.037(5) 0.012(4) 0.011(4) 0.008(4) O12 0.062(6) 0.034(4) 0.036(5) -0.002(4) 0.017(5) 0.005(4) O13 0.086(7) 0.050(5) 0.041(6) -0.007(4) 0.020(5) 0.006(4) O14 0.083(7) 0.040(5) 0.071(7) 0.002(4) 0.002(6) -0.011(4) O15 0.108(8) 0.044(5) 0.050(7) -0.006(4) 0.034(6) 0.004(5) O16 0.042(12) 0.027(7) 0.048(11) -0.013(6) -0.001(9) -0.005(7) O17 0.082(7) 0.041(5) 0.061(7) -0.010(4) 0.032(5) 0.001(4) O18 0.060(6) 0.080(6) 0.048(7) 0.001(5) 0.031(5) 0.010(4) U1 0.0363(3) 0.0351(2) 0.0252(3) 0.00299(17) 0.00405(18) 0.00091(17) U2 0.0412(3) 0.0366(2) 0.0265(3) -0.00141(18) 0.00566(19) 0.00389(18) _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 1.356(11) . ? C1 C6 1.367(15) . ? C1 C2 1.418(15) . ? C2 O1 1.370(13) . ? C2 C3 1.389(14) . ? C3 C4 1.383(18) . ? C3 H3 0.9300 . ? C4 C5 1.347(18) . ? C4 H4 0.9300 . ? C5 C6 1.396(15) . ? C5 H5 0.9300 . ? C6 C7 1.461(18) . ? C7 N1 1.262(14) . ? C7 H7 0.9300 . ? C8 N1 1.477(16) . ? C8 C9 1.485(17) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 N2 1.490(15) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.257(14) . ? C10 C12 1.462(16) . ? C10 H10 0.9300 . ? C11 O3 1.360(11) . ? C11 C16 1.388(15) . ? C11 C12 1.409(15) . ? C12 C13 1.422(15) . ? C13 C14 1.324(17) . ? C13 H13 0.9300 . ? C14 C15 1.379(17) . ? C14 H14 0.9300 . ? C15 C16 1.355(14) . ? C15 H15 0.9300 . ? C16 O4 1.383(13) . ? C17 O1 1.434(14) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 O4 1.449(13) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? Cu1 N1 1.902(9) . ? Cu1 O3 1.906(7) . ? Cu1 N2 1.908(9) . ? Cu1 O2 1.912(7) . ? N3 O8 1.224(12) . ? N3 O9 1.263(13) . ? N3 O7 1.264(12) . ? N4 O18 1.228(12) . ? N4 O16 1.249(19) . ? N4 O17 1.279(12) . ? N4 O16A 1.34(3) . ? N5 O14 1.212(11) . ? N5 O13 1.233(11) . ? N5 O15 1.278(12) . ? O1 U1 2.655(7) . ? O2 U1 2.400(7) . ? O3 U1 2.392(7) . ? O4 U1 2.625(7) . ? O5 U1 1.730(7) . ? O6 U1 1.755(8) . ? O7 U1 2.478(7) . ? O9 U1 2.503(8) . ? O10 U2 1.726(8) . ? O11 U2 1.755(8) . ? O12 U2 2.327(8) . ? O12 U2 2.342(7) 5_667 ? O12 H12H 0.79(2) . ? O13 U2 2.535(8) . ? O15 U2 2.559(8) . ? O16 U2 2.498(19) . ? O17 U2 2.527(8) . ? U2 O12 2.342(7) 5_667 ? U2 O16A 2.64(3) . ? U2 U2 3.8791(9) 5_667 ? 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 C6 127.6(11) . . ? O2 C1 C2 114.2(9) . . ? C6 C1 C2 118.3(10) . . ? O1 C2 C3 124.7(12) . . ? O1 C2 C1 114.7(9) . . ? C3 C2 C1 120.6(11) . . ? C4 C3 C2 118.6(13) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C5 C4 C3 121.5(12) . . ? C5 C4 H4 119.2 . . ? C3 C4 H4 119.2 . . ? C4 C5 C6 120.2(13) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C1 C6 C5 120.8(12) . . ? C1 C6 C7 121.5(10) . . ? C5 C6 C7 117.7(11) . . ? N1 C7 C6 127.0(11) . . ? N1 C7 H7 116.5 . . ? C6 C7 H7 116.5 . . ? N1 C8 C9 109.7(10) . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 N2 108.1(11) . . ? C8 C9 H9A 110.1 . . ? N2 C9 H9A 110.1 . . ? C8 C9 H9B 110.1 . . ? N2 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? N2 C10 C12 124.1(10) . . ? N2 C10 H10 117.9 . . ? C12 C10 H10 117.9 . . ? O3 C11 C16 116.8(10) . . ? O3 C11 C12 123.3(10) . . ? C16 C11 C12 119.9(9) . . ? C11 C12 C13 116.8(11) . . ? C11 C12 C10 124.7(10) . . ? C13 C12 C10 118.4(11) . . ? C14 C13 C12 122.2(12) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? C13 C14 C15 119.9(11) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 121.2(12) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C15 C16 O4 127.6(11) . . ? C15 C16 C11 120.0(11) . . ? O4 C16 C11 112.3(9) . . ? O1 C17 H17A 109.5 . . ? O1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 C18 H18A 109.5 . . ? O4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 Cu1 O3 178.3(4) . . ? N1 Cu1 N2 86.0(4) . . ? O3 Cu1 N2 95.7(4) . . ? N1 Cu1 O2 96.0(4) . . ? O3 Cu1 O2 82.3(3) . . ? N2 Cu1 O2 176.1(4) . . ? C7 N1 C8 122.8(10) . . ? C7 N1 Cu1 124.9(9) . . ? C8 N1 Cu1 112.3(7) . . ? C10 N2 C9 120.6(10) . . ? C10 N2 Cu1 126.7(9) . . ? C9 N2 Cu1 112.6(7) . . ? O8 N3 O9 122.5(11) . . ? O8 N3 O7 121.9(11) . . ? O9 N3 O7 115.6(10) . . ? O18 N4 O16 125.4(13) . . ? O18 N4 O17 122.2(10) . . ? O16 N4 O17 112.2(13) . . ? O18 N4 O16A 118.1(18) . . ? O16 N4 O16A 21.5(15) . . ? O17 N4 O16A 117.3(18) . . ? O14 N5 O13 123.4(12) . . ? O14 N5 O15 122.3(10) . . ? O13 N5 O15 114.3(10) . . ? C2 O1 C17 115.8(9) . . ? C2 O1 U1 119.1(6) . . ? C17 O1 U1 125.0(7) . . ? C1 O2 Cu1 122.5(7) . . ? C1 O2 U1 129.5(6) . . ? Cu1 O2 U1 106.4(3) . . ? C11 O3 Cu1 124.3(7) . . ? C11 O3 U1 128.7(6) . . ? Cu1 O3 U1 107.0(3) . . ? C16 O4 C18 114.0(9) . . ? C16 O4 U1 121.2(6) . . ? C18 O4 U1 124.1(7) . . ? N3 O7 U1 97.3(7) . . ? N3 O9 U1 96.1(7) . . ? U2 O12 U2 112.4(3) . 5_667 ? U2 O12 H12H 106(2) . . ? U2 O12 H12H 68(8) 5_667 . ? N5 O13 U2 99.6(7) . . ? N5 O15 U2 97.1(6) . . ? N4 O16 U2 100.1(11) . . ? N4 O17 U2 97.8(6) . . ? O5 U1 O6 177.1(3) . . ? O5 U1 O3 86.0(3) . . ? O6 U1 O3 96.8(3) . . ? O5 U1 O2 86.1(3) . . ? O6 U1 O2 95.4(3) . . ? O3 U1 O2 63.2(2) . . ? O5 U1 O7 87.1(3) . . ? O6 U1 O7 90.1(3) . . ? O3 U1 O7 170.1(3) . . ? O2 U1 O7 123.4(3) . . ? O5 U1 O9 82.1(3) . . ? O6 U1 O9 96.1(3) . . ? O3 U1 O9 120.9(3) . . ? O2 U1 O9 167.1(3) . . ? O7 U1 O9 50.9(3) . . ? O5 U1 O4 100.6(3) . . ? O6 U1 O4 80.6(3) . . ? O3 U1 O4 60.3(2) . . ? O2 U1 O4 122.4(2) . . ? O7 U1 O4 114.1(3) . . ? O9 U1 O4 65.5(3) . . ? O5 U1 O1 96.9(3) . . ? O6 U1 O1 81.8(3) . . ? O3 U1 O1 123.0(2) . . ? O2 U1 O1 60.2(2) . . ? O7 U1 O1 65.0(3) . . ? O9 U1 O1 115.9(3) . . ? O4 U1 O1 162.4(3) . . ? O10 U2 O11 177.2(4) . . ? O10 U2 O12 88.2(4) . . ? O11 U2 O12 94.3(3) . . ? O10 U2 O12 93.3(3) . 5_667 ? O11 U2 O12 88.7(3) . 5_667 ? O12 U2 O12 67.6(3) . 5_667 ? O10 U2 O16 86.0(5) . . ? O11 U2 O16 93.2(5) . . ? O12 U2 O16 134.0(4) . . ? O12 U2 O16 67.2(4) 5_667 . ? O10 U2 O17 90.1(3) . . ? O11 U2 O17 87.4(3) . . ? O12 U2 O17 176.1(3) . . ? O12 U2 O17 116.0(3) 5_667 . ? O16 U2 O17 49.4(4) . . ? O10 U2 O13 93.3(3) . . ? O11 U2 O13 86.6(3) . . ? O12 U2 O13 66.3(3) . . ? O12 U2 O13 133.2(3) 5_667 . ? O16 U2 O13 159.6(4) . . ? O17 U2 O13 110.3(3) . . ? O10 U2 O15 88.5(3) . . ? O11 U2 O15 89.4(3) . . ? O12 U2 O15 114.8(3) . . ? O12 U2 O15 177.0(3) 5_667 . ? O16 U2 O15 110.6(4) . . ? O17 U2 O15 61.6(3) . . ? O13 U2 O15 48.9(3) . . ? O10 U2 O16A 96.3(7) . . ? O11 U2 O16A 83.0(6) . . ? O12 U2 O16A 132.5(7) . . ? O12 U2 O16A 64.9(7) 5_667 . ? O16 U2 O16A 10.5(8) . . ? O17 U2 O16A 51.2(7) . . ? O13 U2 O16A 159.0(7) . . ? O15 U2 O16A 112.6(7) . . ? O10 U2 U2 90.9(3) . 5_667 ? O11 U2 U2 91.8(3) . 5_667 ? O12 U2 U2 33.94(19) . 5_667 ? O12 U2 U2 33.69(19) 5_667 5_667 ? O16 U2 U2 100.5(4) . 5_667 ? O17 U2 U2 149.69(19) . 5_667 ? O13 U2 U2 99.90(18) . 5_667 ? O15 U2 U2 148.7(2) . 5_667 ? O16A U2 U2 98.6(7) . 5_667 ? N4 O16A U2 91.1(16) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.828 _refine_diff_density_min -2.082 _refine_diff_density_rms 0.236 _database_code_depnum_ccdc_archive 'CCDC 954923' ####################################################################### # # 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_pn-OEt--CuII-mono _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 Cu N2 O5' _chemical_formula_weight 449.98 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' H H 0.0000 0.0000 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.4930(17) _cell_length_b 10.3764(14) _cell_length_c 18.9139(18) _cell_angle_alpha 90.00 _cell_angle_beta 121.136(6) _cell_angle_gamma 90.00 _cell_volume 2098.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 1912 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 20.56 _exptl_crystal_description hexagonal _exptl_crystal_colour green _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 940 _exptl_absorpt_coefficient_mu 1.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8818 _exptl_absorpt_correction_T_max 0.9095 _exptl_absorpt_process_details SADABS _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 14318 _diffrn_reflns_av_R_equivalents 0.0617 _diffrn_reflns_av_sigmaI/netI 0.0621 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.17 _reflns_number_total 3762 _reflns_number_gt 2646 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0500P)^2^+0.0020P] 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 3762 _refine_ls_number_parameters 272 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0729 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1117 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 -0.0098(3) 0.3014(3) 0.9686(2) 0.0372(8) Uani 1 1 d . . . C2 C 0.0443(3) 0.2048(3) 1.0307(2) 0.0415(9) Uani 1 1 d . . . C3 C 0.0050(4) 0.1871(4) 1.0858(2) 0.0516(10) Uani 1 1 d . . . H3 H 0.0413 0.1233 1.1260 0.062 Uiso 1 1 calc R . . C4 C -0.0894(4) 0.2646(4) 1.0814(2) 0.0561(11) Uani 1 1 d . . . H4 H -0.1144 0.2534 1.1196 0.067 Uiso 1 1 calc R . . C5 C -0.1445(3) 0.3555(4) 1.0226(2) 0.0496(10) Uani 1 1 d . . . H5 H -0.2077 0.4059 1.0205 0.060 Uiso 1 1 calc R . . C6 C -0.1083(3) 0.3761(4) 0.9638(2) 0.0388(8) Uani 1 1 d . . . C7 C -0.1753(3) 0.4678(4) 0.8993(2) 0.0456(10) Uani 1 1 d . . . H7 H -0.2415 0.5095 0.8989 0.055 Uiso 1 1 calc R . . C8 C -0.2456(4) 0.5895(5) 0.7777(2) 0.0717(14) Uani 1 1 d . . . H8A H -0.3183 0.5990 0.7831 0.086 Uiso 1 1 calc R . . H8B H -0.2073 0.6736 0.7851 0.086 Uiso 1 1 calc R . . C9 C -0.2845(4) 0.5394(5) 0.6947(2) 0.0741(14) Uani 1 1 d . . . H9A H -0.3643 0.5779 0.6552 0.089 Uiso 1 1 calc R . . H9B H -0.2973 0.4472 0.6944 0.089 Uiso 1 1 calc R . . C10 C -0.1950(3) 0.5640(4) 0.6670(2) 0.0605(12) Uani 1 1 d . . . H10A H -0.2015 0.6536 0.6507 0.073 Uiso 1 1 calc R . . H10B H -0.2184 0.5115 0.6187 0.073 Uiso 1 1 calc R . . C11 C 0.0179(4) 0.5886(3) 0.7173(2) 0.0465(10) Uani 1 1 d . . . H11 H -0.0135 0.6441 0.6723 0.056 Uiso 1 1 calc R . . C12 C 0.2075(3) 0.4727(3) 0.8227(2) 0.0384(8) Uani 1 1 d . . . C13 C 0.1511(3) 0.5716(3) 0.7637(2) 0.0401(9) Uani 1 1 d . . . C14 C 0.2247(4) 0.6505(4) 0.7445(2) 0.0506(10) Uani 1 1 d . . . H14 H 0.1865 0.7160 0.7058 0.061 Uiso 1 1 calc R . . C15 C 0.3493(4) 0.6328(4) 0.7812(2) 0.0597(11) Uani 1 1 d . . . H15 H 0.3965 0.6870 0.7687 0.072 Uiso 1 1 calc R . . C16 C 0.4072(4) 0.5322(4) 0.8382(2) 0.0564(11) Uani 1 1 d . . . H16 H 0.4929 0.5193 0.8631 0.068 Uiso 1 1 calc R . . C17 C 0.3384(3) 0.4530(4) 0.8576(2) 0.0443(9) Uani 1 1 d . . . C18 C 0.2064(4) 0.0467(4) 1.0947(2) 0.0647(12) Uani 1 1 d . . . H18A H 0.1526 -0.0225 1.0926 0.078 Uiso 1 1 calc R . . H18B H 0.2419 0.0894 1.1478 0.078 Uiso 1 1 calc R . . C19 C 0.3079(5) -0.0058(5) 1.0836(3) 0.0942(18) Uani 1 1 d . . . H19A H 0.2730 -0.0341 1.0275 0.141 Uiso 1 1 calc R . . H19B H 0.3472 -0.0773 1.1203 0.141 Uiso 1 1 calc R . . H19C H 0.3689 0.0602 1.0957 0.141 Uiso 1 1 calc R . . C20 C 0.5180(3) 0.3274(4) 0.9517(2) 0.0584(11) Uani 1 1 d . . . H20A H 0.5651 0.4032 0.9818 0.070 Uiso 1 1 calc R . . H20B H 0.5399 0.3062 0.9108 0.070 Uiso 1 1 calc R . . C21 C 0.5486(4) 0.2169(4) 1.0100(2) 0.0654(12) Uani 1 1 d . . . H21A H 0.5244 0.2378 1.0493 0.098 Uiso 1 1 calc R . . H21B H 0.6368 0.2003 1.0387 0.098 Uiso 1 1 calc R . . H21C H 0.5040 0.1415 0.9795 0.098 Uiso 1 1 calc R . . Cu1 Cu -0.01113(4) 0.44248(4) 0.83454(2) 0.03707(16) Uani 1 1 d . . . H5A H 0.752(3) 0.798(5) 0.483(3) 0.10(2) Uiso 1 1 d D . . H5B H 0.675(4) 0.849(5) 0.499(2) 0.08(2) Uiso 1 1 d D . . N1 N -0.1550(3) 0.4994(3) 0.84185(18) 0.0437(7) Uani 1 1 d . . . N2 N -0.0633(3) 0.5358(3) 0.73085(17) 0.0450(8) Uani 1 1 d . . . O1 O 0.1366(2) 0.1362(2) 1.02969(15) 0.0531(7) Uani 1 1 d . . . O2 O 0.0338(2) 0.3169(2) 0.91938(13) 0.0379(6) Uani 1 1 d . . . O3 O 0.1468(2) 0.3998(2) 0.84647(14) 0.0448(6) Uani 1 1 d . . . O4 O 0.3869(2) 0.3524(3) 0.91225(15) 0.0565(7) Uani 1 1 d . . . O5 O 0.6866(3) 0.8332(4) 0.4640(2) 0.0698(9) Uani 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 0.035(2) 0.034(2) 0.0388(19) -0.0045(15) 0.0167(17) -0.0080(16) C2 0.045(2) 0.039(2) 0.042(2) -0.0011(16) 0.0233(18) -0.0040(17) C3 0.061(3) 0.050(2) 0.047(2) 0.0049(18) 0.030(2) -0.006(2) C4 0.060(3) 0.070(3) 0.053(2) -0.004(2) 0.039(2) -0.011(2) C5 0.042(2) 0.059(3) 0.058(2) -0.010(2) 0.033(2) -0.005(2) C6 0.032(2) 0.046(2) 0.0364(19) -0.0090(17) 0.0161(16) -0.0061(17) C7 0.031(2) 0.052(3) 0.050(2) -0.0115(19) 0.0180(18) 0.0026(17) C8 0.052(3) 0.089(4) 0.062(3) 0.008(2) 0.021(2) 0.036(2) C9 0.051(3) 0.087(4) 0.056(3) 0.023(3) 0.007(2) 0.014(2) C10 0.040(2) 0.068(3) 0.050(2) 0.013(2) 0.0060(19) 0.004(2) C11 0.064(3) 0.037(2) 0.036(2) 0.0014(16) 0.024(2) 0.0061(19) C12 0.044(2) 0.037(2) 0.0385(19) -0.0035(16) 0.0245(18) -0.0002(17) C13 0.052(2) 0.038(2) 0.0397(19) -0.0048(16) 0.0301(18) -0.0029(18) C14 0.067(3) 0.042(2) 0.051(2) -0.0030(19) 0.037(2) -0.008(2) C15 0.067(3) 0.064(3) 0.064(3) -0.013(2) 0.045(2) -0.022(2) C16 0.052(3) 0.068(3) 0.053(2) -0.012(2) 0.030(2) -0.007(2) C17 0.042(2) 0.050(2) 0.042(2) -0.0003(18) 0.0230(18) 0.0004(19) C18 0.089(3) 0.056(3) 0.054(2) 0.020(2) 0.040(3) 0.023(2) C19 0.118(5) 0.095(4) 0.085(4) 0.039(3) 0.064(4) 0.065(4) C20 0.033(2) 0.074(3) 0.062(3) -0.010(2) 0.020(2) 0.005(2) C21 0.045(2) 0.080(3) 0.059(3) -0.002(2) 0.018(2) 0.023(2) Cu1 0.0346(3) 0.0368(3) 0.0363(2) 0.00426(19) 0.01586(19) 0.0044(2) N1 0.0368(17) 0.0477(18) 0.0408(17) 0.0001(15) 0.0160(15) 0.0074(15) N2 0.0446(19) 0.044(2) 0.0395(17) 0.0036(14) 0.0171(15) 0.0028(15) O1 0.0660(18) 0.0482(17) 0.0551(15) 0.0187(13) 0.0385(14) 0.0199(14) O2 0.0414(14) 0.0390(14) 0.0397(13) 0.0045(11) 0.0255(12) 0.0079(11) O3 0.0404(15) 0.0466(15) 0.0526(15) 0.0132(12) 0.0278(13) 0.0099(12) O4 0.0368(15) 0.070(2) 0.0621(16) 0.0092(15) 0.0251(13) 0.0076(14) O5 0.050(2) 0.092(3) 0.067(2) 0.008(2) 0.0306(19) 0.0033(19) _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 1.309(4) . ? C1 C6 1.417(5) . ? C1 C2 1.421(5) . ? C2 O1 1.364(4) . ? C2 C3 1.376(5) . ? C3 C4 1.393(5) . ? C3 H3 0.9300 . ? C4 C5 1.345(5) . ? C4 H4 0.9300 . ? C5 C6 1.417(5) . ? C5 H5 0.9300 . ? C6 C7 1.429(5) . ? C7 N1 1.279(4) . ? C7 H7 0.9300 . ? C8 C9 1.476(5) . ? C8 N1 1.486(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.482(6) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N2 1.482(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 N2 1.290(4) . ? C11 C13 1.435(5) . ? C11 H11 0.9300 . ? C12 O3 1.304(4) . ? C12 C13 1.408(5) . ? C12 C17 1.427(5) . ? C13 C14 1.411(5) . ? C14 C15 1.349(5) . ? C14 H14 0.9300 . ? C15 C16 1.403(5) . ? C15 H15 0.9300 . ? C16 C17 1.369(5) . ? C16 H16 0.9300 . ? C17 O4 1.371(4) . ? C18 O1 1.423(4) . ? C18 C19 1.492(6) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O4 1.430(4) . ? C20 C21 1.498(5) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? Cu1 O2 1.912(2) . ? Cu1 O3 1.918(2) . ? Cu1 N1 1.963(3) . ? Cu1 N2 1.971(3) . ? O5 H5A 0.787(19) . ? O5 H5B 0.767(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 C6 123.7(3) . . ? O2 C1 C2 118.6(3) . . ? C6 C1 C2 117.7(3) . . ? O1 C2 C3 125.2(3) . . ? O1 C2 C1 113.7(3) . . ? C3 C2 C1 121.1(4) . . ? C2 C3 C4 120.0(4) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 121.3(4) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 119.1(3) . . ? C1 C6 C7 121.6(3) . . ? C5 C6 C7 119.2(3) . . ? N1 C7 C6 127.6(3) . . ? N1 C7 H7 116.2 . . ? C6 C7 H7 116.2 . . ? C9 C8 N1 109.9(3) . . ? C9 C8 H8A 109.7 . . ? N1 C8 H8A 109.7 . . ? C9 C8 H8B 109.7 . . ? N1 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? C8 C9 C10 114.9(4) . . ? C8 C9 H9A 108.5 . . ? C10 C9 H9A 108.5 . . ? C8 C9 H9B 108.5 . . ? C10 C9 H9B 108.5 . . ? H9A C9 H9B 107.5 . . ? C9 C10 N2 113.6(3) . . ? C9 C10 H10A 108.8 . . ? N2 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? N2 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? N2 C11 C13 127.5(3) . . ? N2 C11 H11 116.3 . . ? C13 C11 H11 116.3 . . ? O3 C12 C13 123.6(3) . . ? O3 C12 C17 119.3(3) . . ? C13 C12 C17 117.0(3) . . ? C12 C13 C14 120.1(4) . . ? C12 C13 C11 121.4(3) . . ? C14 C13 C11 118.4(3) . . ? C15 C14 C13 121.4(4) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 119.7(4) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 120.4(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 O4 124.4(4) . . ? C16 C17 C12 121.3(4) . . ? O4 C17 C12 114.3(3) . . ? O1 C18 C19 107.6(3) . . ? O1 C18 H18A 110.2 . . ? C19 C18 H18A 110.2 . . ? O1 C18 H18B 110.2 . . ? C19 C18 H18B 110.2 . . ? H18A C18 H18B 108.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O4 C20 C21 108.1(3) . . ? O4 C20 H20A 110.1 . . ? C21 C20 H20A 110.1 . . ? O4 C20 H20B 110.1 . . ? C21 C20 H20B 110.1 . . ? H20A C20 H20B 108.4 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O2 Cu1 O3 84.61(9) . . ? O2 Cu1 N1 91.61(11) . . ? O3 Cu1 N1 169.89(11) . . ? O2 Cu1 N2 166.42(11) . . ? O3 Cu1 N2 91.22(11) . . ? N1 Cu1 N2 94.50(12) . . ? C7 N1 C8 116.9(3) . . ? C7 N1 Cu1 125.0(3) . . ? C8 N1 Cu1 118.0(3) . . ? C11 N2 C10 114.2(3) . . ? C11 N2 Cu1 121.1(3) . . ? C10 N2 Cu1 124.4(3) . . ? C2 O1 C18 118.2(3) . . ? C1 O2 Cu1 129.1(2) . . ? C12 O3 Cu1 124.9(2) . . ? C17 O4 C20 118.2(3) . . ? H5A O5 H5B 109(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.17 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.607 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.082 _database_code_depnum_ccdc_archive 'CCDC 955863'