# Electronic Supplementary Material (ESI) for Dalton Transactions # 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 #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1363272479.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cu N4 O13 U' _chemical_formula_weight 719.81 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 7.7582(4) _cell_length_b 11.0274(8) _cell_length_c 12.1812(10) _cell_angle_alpha 66.717(3) _cell_angle_beta 85.541(4) _cell_angle_gamma 87.653(4) _cell_volume 954.31(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 45684 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 30.51 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light green' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.505 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 670 _exptl_absorpt_coefficient_mu 9.667 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.316 _exptl_absorpt_correction_T_max 0.679 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and ten \w scans with 2\% steps (628 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 45684 _diffrn_reflns_av_R_equivalents 0.0787 _diffrn_reflns_av_sigmaI/netI 0.1011 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5819 _reflns_number_gt 4429 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by Patterson map interpretation and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O13 were found on a Fourier-difference map and all the others were introduced at calculated positions; all were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0058P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary heavy _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 5819 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0600 _refine_ls_wR_factor_gt 0.0553 _refine_ls_goodness_of_fit_ref 0.923 _refine_ls_restrained_S_all 0.923 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.269 _refine_diff_density_min -2.430 _refine_diff_density_rms 0.354 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 U U 0.75242(2) 0.758399(15) 0.702321(15) 0.02324(5) Uani 1 1 d . . . Cu Cu 0.30211(7) 0.74830(5) 0.35372(5) 0.02540(13) Uani 1 1 d . . . O1 O 0.6433(5) 0.6251(3) 0.8138(3) 0.0354(8) Uani 1 1 d . . . O2 O 0.8626(4) 0.8914(3) 0.5914(3) 0.0337(8) Uani 1 1 d . . . O3 O 0.7022(4) 0.6731(3) 0.5502(3) 0.0271(7) Uani 1 1 d . . . O4 O 0.5363(4) 0.6823(3) 0.4050(3) 0.0288(7) Uani 1 1 d . . . O5 O 0.4803(4) 0.8303(3) 0.6105(3) 0.0327(8) Uani 1 1 d . . . O6 O 0.3000(4) 0.8224(3) 0.4787(3) 0.0301(7) Uani 1 1 d . . . O7 O 0.5804(4) 0.9172(3) 0.7681(3) 0.0308(8) Uani 1 1 d . . . O8 O 0.8086(4) 0.8390(3) 0.8619(3) 0.0293(7) Uani 1 1 d . . . O9 O 0.6368(4) 0.9722(3) 0.9147(3) 0.0315(8) Uani 1 1 d . . . O10 O 1.0273(5) 0.6842(4) 0.8046(3) 0.0481(10) Uani 1 1 d . . . O11 O 0.9816(4) 0.6037(3) 0.6754(3) 0.0388(9) Uani 1 1 d . . . O12 O 1.2197(6) 0.5528(5) 0.7691(4) 0.0835(17) Uani 1 1 d . . . O13 O 0.1767(5) 0.5649(3) 0.4756(3) 0.0413(10) Uani 1 1 d . . . H13A H 0.1859 0.4978 0.4786 0.050 Uiso 1 1 d R . . H13B H 0.0911 0.5805 0.5306 0.050 Uiso 1 1 d R . . N1 N 0.6731(5) 0.9118(3) 0.8511(3) 0.0259(8) Uani 1 1 d . . . N2 N 1.0817(6) 0.6111(5) 0.7509(4) 0.0506(13) Uani 1 1 d . . . N3 N 0.0852(5) 0.8352(3) 0.2846(3) 0.0244(8) Uani 1 1 d . . . N4 N 0.3307(5) 0.7170(3) 0.2044(3) 0.0241(8) Uani 1 1 d . . . C1 C 0.5706(6) 0.7094(4) 0.4911(4) 0.0261(10) Uani 1 1 d . . . C2 C 0.4366(6) 0.7954(4) 0.5300(4) 0.0272(10) Uani 1 1 d . . . C3 C -0.0290(6) 0.8977(4) 0.3325(4) 0.0274(10) Uani 1 1 d . . . H3 H -0.0052 0.9072 0.4023 0.033 Uiso 1 1 calc R . . C4 C -0.1811(6) 0.9482(4) 0.2801(4) 0.0293(11) Uani 1 1 d . . . H4 H -0.2580 0.9935 0.3133 0.035 Uiso 1 1 calc R . . C5 C -0.2187(6) 0.9319(4) 0.1798(4) 0.0316(11) Uani 1 1 d . . . H5 H -0.3221 0.9644 0.1445 0.038 Uiso 1 1 calc R . . C6 C -0.1009(6) 0.8659(4) 0.1303(4) 0.0325(11) Uani 1 1 d . . . H6 H -0.1245 0.8532 0.0620 0.039 Uiso 1 1 calc R . . C7 C 0.0518(6) 0.8196(4) 0.1847(4) 0.0251(10) Uani 1 1 d . . . C8 C 0.1938(6) 0.7546(4) 0.1367(4) 0.0242(10) Uani 1 1 d . . . C9 C 0.1931(6) 0.7402(4) 0.0288(4) 0.0294(10) Uani 1 1 d . . . H9 H 0.0972 0.7661 -0.0168 0.035 Uiso 1 1 calc R . . C10 C 0.3381(6) 0.6865(4) -0.0100(4) 0.0299(11) Uani 1 1 d . . . H10 H 0.3412 0.6764 -0.0823 0.036 Uiso 1 1 calc R . . C11 C 0.4763(6) 0.6486(4) 0.0596(4) 0.0293(11) Uani 1 1 d . . . H11 H 0.5741 0.6119 0.0350 0.035 Uiso 1 1 calc R . . C12 C 0.4704(6) 0.6650(4) 0.1668(4) 0.0280(10) Uani 1 1 d . . . H12 H 0.5652 0.6394 0.2136 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U 0.02188(10) 0.02941(9) 0.02337(9) -0.01540(7) -0.00573(7) 0.00506(6) Cu 0.0236(3) 0.0330(3) 0.0251(3) -0.0167(2) -0.0090(2) 0.0069(2) O1 0.043(2) 0.0329(16) 0.031(2) -0.0140(15) 0.0013(17) -0.0012(15) O2 0.038(2) 0.0357(17) 0.032(2) -0.0193(15) 0.0082(16) -0.0096(15) O3 0.0270(18) 0.0342(16) 0.0292(18) -0.0215(14) -0.0115(15) 0.0096(14) O4 0.0256(18) 0.0389(17) 0.0305(19) -0.0220(15) -0.0122(15) 0.0097(14) O5 0.032(2) 0.0477(18) 0.033(2) -0.0299(16) -0.0135(16) 0.0124(16) O6 0.0266(19) 0.0379(16) 0.0339(19) -0.0218(15) -0.0114(15) 0.0092(14) O7 0.0260(19) 0.0459(18) 0.0291(19) -0.0232(15) -0.0125(15) 0.0122(15) O8 0.0255(18) 0.0446(18) 0.0281(18) -0.0251(15) -0.0093(15) 0.0103(15) O9 0.0296(19) 0.0426(17) 0.035(2) -0.0289(16) -0.0075(15) 0.0068(15) O10 0.038(2) 0.076(2) 0.057(3) -0.053(2) -0.0278(19) 0.0315(19) O11 0.032(2) 0.054(2) 0.050(2) -0.0392(18) -0.0205(17) 0.0159(16) O12 0.062(3) 0.128(4) 0.103(4) -0.088(3) -0.060(3) 0.071(3) O13 0.048(2) 0.0294(16) 0.050(2) -0.0220(16) 0.0111(19) 0.0033(16) N1 0.022(2) 0.0281(18) 0.028(2) -0.0118(17) -0.0059(17) 0.0024(16) N2 0.045(3) 0.076(3) 0.052(3) -0.046(3) -0.029(2) 0.029(3) N3 0.021(2) 0.0319(18) 0.024(2) -0.0152(16) -0.0050(17) 0.0054(15) N4 0.026(2) 0.0258(17) 0.024(2) -0.0135(16) -0.0052(17) 0.0047(16) C1 0.027(3) 0.025(2) 0.025(3) -0.0092(19) -0.003(2) 0.0021(18) C2 0.028(3) 0.031(2) 0.027(3) -0.016(2) -0.006(2) 0.0020(19) C3 0.026(3) 0.033(2) 0.025(3) -0.014(2) -0.001(2) -0.0024(19) C4 0.020(2) 0.037(2) 0.034(3) -0.018(2) -0.002(2) 0.0071(19) C5 0.022(3) 0.044(3) 0.033(3) -0.019(2) -0.009(2) 0.008(2) C6 0.030(3) 0.045(3) 0.028(3) -0.020(2) -0.010(2) 0.007(2) C7 0.027(3) 0.029(2) 0.023(2) -0.0140(19) -0.005(2) 0.0034(19) C8 0.027(3) 0.025(2) 0.023(2) -0.0114(18) -0.006(2) 0.0022(18) C9 0.025(3) 0.042(2) 0.024(3) -0.015(2) -0.011(2) 0.004(2) C10 0.037(3) 0.034(2) 0.022(3) -0.015(2) -0.001(2) -0.001(2) C11 0.032(3) 0.033(2) 0.024(3) -0.013(2) -0.001(2) 0.007(2) C12 0.029(3) 0.027(2) 0.030(3) -0.012(2) -0.008(2) 0.0038(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 U O2 1.750(3) . ? U O1 1.751(3) . ? U O5 2.422(3) . ? U O3 2.447(3) . ? U O10 2.496(3) . ? U O7 2.498(3) . ? U O11 2.506(3) . ? U O8 2.507(3) . ? Cu N4 1.976(4) . ? Cu N3 1.977(4) . ? Cu O4 1.982(3) . ? Cu O6 1.991(3) . ? Cu O13 2.192(3) . ? O3 C1 1.255(5) . ? O4 C1 1.249(5) . ? O5 C2 1.260(5) . ? O6 C2 1.238(6) . ? O7 N1 1.268(5) . ? O8 N1 1.279(4) . ? O9 N1 1.216(4) . ? O10 N2 1.265(5) . ? O11 N2 1.277(5) . ? O12 N2 1.216(5) . ? O13 H13A 0.7271 . ? O13 H13B 0.9650 . ? N3 C3 1.337(5) . ? N3 C7 1.340(5) . ? N4 C12 1.339(5) . ? N4 C8 1.345(6) . ? C1 C2 1.550(6) . ? C3 C4 1.376(6) . ? C3 H3 0.9300 . ? C4 C5 1.359(6) . ? C4 H4 0.9300 . ? C5 C6 1.390(6) . ? C5 H5 0.9300 . ? C6 C7 1.381(6) . ? C6 H6 0.9300 . ? C7 C8 1.496(6) . ? C8 C9 1.385(6) . ? C9 C10 1.386(6) . ? C9 H9 0.9300 . ? C10 C11 1.367(6) . ? C10 H10 0.9300 . ? C11 C12 1.384(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 U O1 179.65(16) . . ? O2 U O5 92.08(14) . . ? O1 U O5 88.26(14) . . ? O2 U O3 88.94(13) . . ? O1 U O3 91.25(13) . . ? O5 U O3 66.23(9) . . ? O2 U O10 89.24(15) . . ? O1 U O10 90.42(15) . . ? O5 U O10 177.72(11) . . ? O3 U O10 115.67(10) . . ? O2 U O7 89.34(12) . . ? O1 U O7 90.75(12) . . ? O5 U O7 64.78(10) . . ? O3 U O7 130.87(10) . . ? O10 U O7 113.39(10) . . ? O2 U O11 89.73(13) . . ? O1 U O11 90.09(13) . . ? O5 U O11 131.04(10) . . ? O3 U O11 64.89(10) . . ? O10 U O11 50.80(10) . . ? O7 U O11 164.18(11) . . ? O2 U O8 92.05(13) . . ? O1 U O8 87.75(13) . . ? O5 U O8 115.26(9) . . ? O3 U O8 178.16(9) . . ? O10 U O8 62.81(10) . . ? O7 U O8 50.71(10) . . ? O11 U O8 113.55(10) . . ? N4 Cu N3 82.52(15) . . ? N4 Cu O4 94.72(14) . . ? N3 Cu O4 172.00(14) . . ? N4 Cu O6 165.79(14) . . ? N3 Cu O6 96.14(13) . . ? O4 Cu O6 84.68(12) . . ? N4 Cu O13 100.76(13) . . ? N3 Cu O13 94.56(14) . . ? O4 Cu O13 93.33(13) . . ? O6 Cu O13 93.45(13) . . ? C1 O3 U 119.9(3) . . ? C1 O4 Cu 110.6(3) . . ? C2 O5 U 121.3(3) . . ? C2 O6 Cu 110.8(3) . . ? N1 O7 U 97.7(2) . . ? N1 O8 U 96.9(2) . . ? N2 O10 U 97.4(3) . . ? N2 O11 U 96.6(2) . . ? Cu O13 H13A 131.0 . . ? Cu O13 H13B 111.6 . . ? H13A O13 H13B 117.3 . . ? O9 N1 O7 122.6(4) . . ? O9 N1 O8 122.8(4) . . ? O7 N1 O8 114.6(3) . . ? O12 N2 O10 122.6(5) . . ? O12 N2 O11 122.3(4) . . ? O10 N2 O11 115.1(4) . . ? C3 N3 C7 120.1(4) . . ? C3 N3 Cu 125.9(3) . . ? C7 N3 Cu 113.8(3) . . ? C12 N4 C8 119.6(4) . . ? C12 N4 Cu 126.2(3) . . ? C8 N4 Cu 114.2(3) . . ? O4 C1 O3 126.6(4) . . ? O4 C1 C2 116.9(4) . . ? O3 C1 C2 116.6(4) . . ? O6 C2 O5 127.4(4) . . ? O6 C2 C1 116.9(4) . . ? O5 C2 C1 115.7(4) . . ? N3 C3 C4 121.1(4) . . ? N3 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.8(4) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 119.3(4) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 118.7(4) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? N3 C7 C6 121.0(4) . . ? N3 C7 C8 114.8(4) . . ? C6 C7 C8 124.1(4) . . ? N4 C8 C9 121.6(4) . . ? N4 C8 C7 114.0(4) . . ? C9 C8 C7 124.3(4) . . ? C8 C9 C10 118.7(4) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C11 C10 C9 119.2(4) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 119.9(4) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? N4 C12 C11 121.1(4) . . ? N4 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O13 H13A O3 0.73 2.18 2.876(4) 159.6 2_666 O13 H13B O11 0.96 2.00 2.932(4) 161.2 1_455 _database_code_depnum_ccdc_archive 'CCDC 929302' ####################################################################### # # 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 #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1363272479.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H8 Cu N4 O11 U' _chemical_formula_weight 685.79 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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 15.6832(8) _cell_length_b 11.7371(3) _cell_length_c 9.2826(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.833(2) _cell_angle_gamma 90.00 _cell_volume 1688.43(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 62661 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 30.51 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light green' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.698 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1268 _exptl_absorpt_coefficient_mu 10.912 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.404 _exptl_absorpt_correction_T_max 0.646 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and six \w scans with 2\% steps (472 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 62661 _diffrn_reflns_av_R_equivalents 0.0647 _diffrn_reflns_av_sigmaI/netI 0.0699 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5156 _reflns_number_gt 4042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms bound to O11 were found on a Fourier-difference map and all the others were introduced at calculated positions; all were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0151P)^2^] 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 5156 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0552 _refine_ls_wR_factor_gt 0.0518 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.898 _refine_diff_density_min -1.796 _refine_diff_density_rms 0.204 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 U U 0.570891(8) 0.362482(12) 0.239457(13) 0.01651(5) Uani 1 1 d . . . Cu Cu 0.81859(3) 0.51536(4) -0.07408(5) 0.02221(11) Uani 1 1 d . . . O1 O 0.53819(16) 0.3597(2) 0.0490(3) 0.0229(6) Uani 1 1 d . . . O2 O 0.60442(16) 0.3705(2) 0.4290(3) 0.0240(6) Uani 1 1 d . . . O3 O 0.60389(15) 0.5642(2) 0.2264(2) 0.0197(6) Uani 1 1 d . . . O4 O 0.55393(14) 0.7423(2) 0.2358(3) 0.0205(6) Uani 1 1 d . . . O5 O 0.44944(15) 0.4826(3) 0.2613(3) 0.0224(6) Uani 1 1 d . . . O6 O 0.39785(15) 0.6610(2) 0.2534(3) 0.0201(5) Uani 1 1 d . . . O7 O 0.71711(15) 0.3303(3) 0.2059(3) 0.0240(6) Uani 1 1 d . . . O8 O 0.73547(16) 0.4666(2) 0.0476(3) 0.0272(6) Uani 1 1 d . . . O9 O 0.88164(16) 0.3772(2) -0.0041(3) 0.0247(6) Uani 1 1 d . . . O10 O 0.85737(16) 0.2170(3) 0.1142(3) 0.0301(7) Uani 1 1 d . . . O11 O 0.75792(15) 0.4401(2) -0.2762(3) 0.0250(6) Uani 1 1 d . . . H11A H 0.7068 0.4312 -0.2994 0.030 Uiso 1 1 d R . . H11B H 0.7802 0.3896 -0.3120 0.030 Uiso 1 1 d R . . N1 N 0.78289(18) 0.6778(3) -0.0712(3) 0.0208(7) Uani 1 1 d . . . N2 N 0.90823(18) 0.5809(3) -0.1786(3) 0.0215(7) Uani 1 1 d . . . N3 N 0.94238(19) 0.7523(3) -0.2947(3) 0.0250(7) Uani 1 1 d . . . N4 N 0.8282(2) 0.8631(3) -0.1303(3) 0.0250(8) Uani 1 1 d . . . C1 C 0.5466(2) 0.6368(3) 0.2358(4) 0.0182(8) Uani 1 1 d . . . C2 C 0.4565(2) 0.5882(4) 0.2512(4) 0.0186(8) Uani 1 1 d . . . C3 C 0.7571(2) 0.3753(3) 0.1122(4) 0.0215(8) Uani 1 1 d . . . C4 C 0.8390(2) 0.3134(4) 0.0723(4) 0.0221(8) Uani 1 1 d . . . C5 C 0.7230(2) 0.7218(4) 0.0031(4) 0.0248(9) Uani 1 1 d . . . H5 H 0.6870 0.6740 0.0464 0.030 Uiso 1 1 calc R . . C6 C 0.7157(2) 0.8388(4) 0.0140(4) 0.0258(9) Uani 1 1 d . . . H6 H 0.6761 0.8711 0.0670 0.031 Uiso 1 1 calc R . . C7 C 0.7686(2) 0.9062(4) -0.0556(4) 0.0268(9) Uani 1 1 d . . . H7 H 0.7629 0.9850 -0.0506 0.032 Uiso 1 1 calc R . . C8 C 0.8323(2) 0.7504(3) -0.1336(4) 0.0192(8) Uani 1 1 d . . . C9 C 0.8991(2) 0.6925(4) -0.2075(4) 0.0227(8) Uani 1 1 d . . . C10 C 0.9669(2) 0.5233(4) -0.2395(4) 0.0246(8) Uani 1 1 d . . . H10 H 0.9746 0.4458 -0.2212 0.030 Uiso 1 1 calc R . . C11 C 1.0162(2) 0.5781(4) -0.3299(4) 0.0260(9) Uani 1 1 d . . . H11 H 1.0580 0.5391 -0.3715 0.031 Uiso 1 1 calc R . . C12 C 1.0014(2) 0.6923(4) -0.3560(4) 0.0275(9) Uani 1 1 d . . . H12 H 1.0331 0.7299 -0.4182 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U 0.01870(7) 0.01320(8) 0.01826(7) 0.00043(6) 0.00480(5) 0.00017(5) Cu 0.0228(2) 0.0179(3) 0.0280(2) 0.0015(2) 0.01076(18) -0.00011(19) O1 0.0295(14) 0.0200(17) 0.0193(12) -0.0017(12) 0.0039(10) -0.0006(11) O2 0.0283(14) 0.0237(18) 0.0195(12) -0.0020(11) 0.0020(10) -0.0017(11) O3 0.0196(12) 0.0160(15) 0.0238(12) 0.0006(11) 0.0042(10) 0.0018(11) O4 0.0202(12) 0.0151(15) 0.0272(13) 0.0000(11) 0.0070(10) 0.0007(10) O5 0.0227(13) 0.0131(15) 0.0335(14) -0.0003(12) 0.0113(11) 0.0002(11) O6 0.0194(12) 0.0160(14) 0.0265(13) -0.0004(11) 0.0090(10) 0.0008(11) O7 0.0207(12) 0.0247(16) 0.0282(13) 0.0031(13) 0.0086(10) 0.0002(11) O8 0.0272(14) 0.0229(17) 0.0346(15) 0.0037(14) 0.0146(12) 0.0020(12) O9 0.0228(13) 0.0237(17) 0.0299(14) 0.0041(13) 0.0110(11) 0.0022(11) O10 0.0277(14) 0.0244(18) 0.0415(16) 0.0073(14) 0.0158(12) 0.0060(13) O11 0.0199(12) 0.0242(17) 0.0315(14) -0.0048(13) 0.0053(11) -0.0051(11) N1 0.0220(15) 0.0191(18) 0.0218(15) -0.0012(14) 0.0052(12) -0.0006(13) N2 0.0229(15) 0.0190(19) 0.0233(15) -0.0006(14) 0.0060(12) -0.0038(14) N3 0.0248(16) 0.025(2) 0.0265(16) 0.0033(15) 0.0069(13) -0.0027(14) N4 0.0270(16) 0.023(2) 0.0251(16) 0.0003(15) 0.0027(13) -0.0013(14) C1 0.0190(16) 0.020(2) 0.0158(16) 0.0010(15) 0.0035(13) -0.0026(15) C2 0.0209(17) 0.018(2) 0.0172(17) 0.0002(15) 0.0052(14) 0.0017(16) C3 0.0166(16) 0.024(2) 0.0242(18) -0.0011(17) 0.0055(14) -0.0020(15) C4 0.0218(18) 0.023(2) 0.0222(18) 0.0004(17) 0.0045(14) 0.0004(16) C5 0.0237(18) 0.029(2) 0.0225(18) 0.0000(18) 0.0046(15) 0.0010(17) C6 0.0259(19) 0.026(2) 0.0245(19) -0.0025(18) 0.0021(15) 0.0034(17) C7 0.030(2) 0.017(2) 0.033(2) 0.0008(19) 0.0021(17) 0.0067(17) C8 0.0193(17) 0.016(2) 0.0210(17) 0.0002(16) -0.0006(14) -0.0018(15) C9 0.0233(18) 0.022(2) 0.0225(18) -0.0034(17) 0.0044(15) -0.0032(16) C10 0.0252(19) 0.019(2) 0.031(2) -0.0024(18) 0.0074(16) -0.0010(17) C11 0.0250(19) 0.029(3) 0.0256(19) -0.0043(18) 0.0077(15) -0.0039(17) C12 0.0250(19) 0.031(3) 0.028(2) -0.0016(19) 0.0086(16) -0.0041(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 U O2 1.760(2) . ? U O1 1.764(2) . ? U O7 2.391(2) . ? U O5 2.403(3) . ? U O6 2.414(3) 2_645 ? U O3 2.430(3) . ? U O4 2.452(2) 2_645 ? Cu O8 1.937(2) . ? Cu O9 1.957(3) . ? Cu N2 1.982(3) . ? Cu N1 1.989(3) . ? Cu O11 2.158(2) . ? O3 C1 1.251(4) . ? O4 C1 1.244(4) . ? O4 U 2.452(2) 2_655 ? O5 C2 1.249(5) . ? O6 C2 1.258(5) . ? O6 U 2.414(3) 2_655 ? O7 C3 1.264(4) . ? O8 C3 1.250(4) . ? O9 C4 1.288(4) . ? O10 C4 1.217(5) . ? O11 H11A 0.8038 . ? O11 H11B 0.7866 . ? N1 C8 1.342(5) . ? N1 C5 1.350(4) . ? N2 C10 1.335(5) . ? N2 C9 1.341(5) . ? N3 C9 1.333(5) . ? N3 C12 1.355(5) . ? N4 C8 1.325(5) . ? N4 C7 1.346(5) . ? C1 C2 1.550(5) . ? C3 C4 1.568(5) . ? C5 C6 1.383(6) . ? C5 H5 0.9300 . ? C6 C7 1.377(5) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C9 1.500(5) . ? C10 C11 1.384(5) . ? C10 H10 0.9300 . ? C11 C12 1.376(6) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? 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 U O1 177.95(12) . . ? O2 U O7 89.62(10) . . ? O1 U O7 90.20(10) . . ? O2 U O5 90.19(10) . . ? O1 U O5 89.05(10) . . ? O7 U O5 153.13(9) . . ? O2 U O6 89.81(10) . 2_645 ? O1 U O6 92.04(10) . 2_645 ? O7 U O6 69.76(9) . 2_645 ? O5 U O6 137.11(8) . 2_645 ? O2 U O3 87.96(10) . . ? O1 U O3 89.99(10) . . ? O7 U O3 86.08(9) . . ? O5 U O3 67.07(8) . . ? O6 U O3 155.75(8) 2_645 . ? O2 U O4 93.29(10) . 2_645 ? O1 U O4 88.26(10) . 2_645 ? O7 U O4 135.79(9) . 2_645 ? O5 U O4 71.03(10) . 2_645 ? O6 U O4 66.15(8) 2_645 2_645 ? O3 U O4 138.08(8) . 2_645 ? O8 Cu O9 85.00(11) . . ? O8 Cu N2 172.40(12) . . ? O9 Cu N2 97.10(12) . . ? O8 Cu N1 93.40(12) . . ? O9 Cu N1 156.74(12) . . ? N2 Cu N1 81.77(13) . . ? O8 Cu O11 98.01(10) . . ? O9 Cu O11 94.70(11) . . ? N2 Cu O11 89.12(11) . . ? N1 Cu O11 108.48(11) . . ? C1 O3 U 120.0(2) . . ? C1 O4 U 119.8(2) . 2_655 ? C2 O5 U 119.7(2) . . ? C2 O6 U 121.3(2) . 2_655 ? C3 O7 U 127.7(2) . . ? C3 O8 Cu 112.1(2) . . ? C4 O9 Cu 112.7(2) . . ? Cu O11 H11A 125.0 . . ? Cu O11 H11B 120.7 . . ? H11A O11 H11B 106.2 . . ? C8 N1 C5 118.1(4) . . ? C8 N1 Cu 114.9(2) . . ? C5 N1 Cu 126.4(3) . . ? C10 N2 C9 118.0(3) . . ? C10 N2 Cu 126.7(3) . . ? C9 N2 Cu 114.6(2) . . ? C9 N3 C12 115.1(4) . . ? C8 N4 C7 115.3(3) . . ? O4 C1 O3 127.7(3) . . ? O4 C1 C2 116.9(3) . . ? O3 C1 C2 115.5(4) . . ? O5 C2 O6 126.8(4) . . ? O5 C2 C1 117.7(3) . . ? O6 C2 C1 115.5(4) . . ? O8 C3 O7 124.2(3) . . ? O8 C3 C4 117.1(3) . . ? O7 C3 C4 118.7(4) . . ? O10 C4 O9 126.8(3) . . ? O10 C4 C3 121.2(3) . . ? O9 C4 C3 112.0(3) . . ? N1 C5 C6 119.3(4) . . ? N1 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C7 C6 C5 118.2(4) . . ? C7 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? N4 C7 C6 122.8(4) . . ? N4 C7 H7 118.6 . . ? C6 C7 H7 118.6 . . ? N4 C8 N1 126.2(3) . . ? N4 C8 C9 120.2(3) . . ? N1 C8 C9 113.6(4) . . ? N3 C9 N2 126.0(3) . . ? N3 C9 C8 119.7(4) . . ? N2 C9 C8 114.3(3) . . ? N2 C10 C11 120.5(4) . . ? N2 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 117.6(4) . . ? C12 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? N3 C12 C11 122.7(4) . . ? N3 C12 H12 118.6 . . ? C11 C12 H12 118.6 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O11 H11A O6 0.80 2.06 2.753(3) 143.5 3_665 O11 H11B O10 0.79 1.94 2.712(4) 167.9 4_565 _database_code_depnum_ccdc_archive 'CCDC 929303' ####################################################################### # # 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 #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1363272479.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H20 Cu2 N14 O20 U2' _chemical_formula_weight 1475.72 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' 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' 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' _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 9.9169(6) _cell_length_b 10.9294(6) _cell_length_c 11.1783(5) _cell_angle_alpha 103.449(3) _cell_angle_beta 110.754(3) _cell_angle_gamma 110.069(3) _cell_volume 973.81(10) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 39442 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 30.51 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light green' _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.516 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 9.470 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.361 _exptl_absorpt_correction_T_max 0.567 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and seven \w scans with 2\% steps (505 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 39442 _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0673 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5940 _reflns_number_gt 5138 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atom bound to O7 was found on a Fourier-difference map and all the others were introduced at calculated positions; all were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0178P)^2^] 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 5940 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0579 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.130 _refine_diff_density_min -2.320 _refine_diff_density_rms 0.219 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 U U 0.265623(15) 0.181929(12) 0.435344(13) 0.01572(4) Uani 1 1 d . . . Cu Cu 0.21630(5) -0.10800(4) 0.11947(4) 0.01763(9) Uani 1 1 d . . . O1 O 0.1142(3) 0.1742(2) 0.2835(3) 0.0202(5) Uani 1 1 d . . . O2 O 0.4225(3) 0.2013(3) 0.5890(3) 0.0200(5) Uani 1 1 d . . . O3 O 0.0726(3) -0.0542(2) 0.3879(2) 0.0181(5) Uani 1 1 d . . . O4 O -0.1093(3) -0.1842(2) 0.4406(3) 0.0191(5) Uani 1 1 d . . . O5 O 0.4743(3) 0.3402(2) 0.3943(3) 0.0209(5) Uani 1 1 d . . . O6 O 0.6527(3) 0.5656(2) 0.4541(3) 0.0213(5) Uani 1 1 d . . . O7 O 0.3212(3) 0.0363(2) 0.3063(2) 0.0183(5) Uani 1 1 d . . . H7 H 0.4227 0.0524 0.3333 0.022 Uiso 1 1 d R . . O8 O 0.6360(3) 0.0950(3) 0.3804(3) 0.0305(6) Uani 1 1 d . . . O9 O 0.5067(3) -0.0513(3) 0.1604(3) 0.0295(6) Uani 1 1 d . . . O10 O 0.7601(3) 0.0059(3) 0.2898(3) 0.0283(6) Uani 1 1 d . . . N1 N 0.2106(3) -0.2645(3) 0.1854(3) 0.0166(6) Uani 1 1 d . . . N2 N 0.1870(3) -0.2542(3) -0.0515(3) 0.0188(6) Uani 1 1 d . . . N3 N 0.2109(4) -0.4666(3) -0.1172(3) 0.0263(7) Uani 1 1 d . . . N4 N 0.1988(4) -0.4929(3) 0.1215(3) 0.0224(7) Uani 1 1 d . . . N5 N 0.2053(3) 0.0372(3) 0.0368(3) 0.0183(6) Uani 1 1 d . . . N6 N 0.0456(3) 0.1451(3) -0.0538(3) 0.0168(6) Uani 1 1 d . . . N7 N 0.6343(4) 0.0154(3) 0.2776(3) 0.0217(7) Uani 1 1 d . . . C1 C -0.0099(4) -0.0687(3) 0.4514(4) 0.0175(7) Uani 1 1 d . . . C2 C 0.5366(4) 0.4725(4) 0.4560(4) 0.0180(7) Uani 1 1 d . . . C3 C 0.2138(4) -0.2654(4) 0.3060(4) 0.0197(7) Uani 1 1 d . . . H3 H 0.2192 -0.1884 0.3682 0.024 Uiso 1 1 calc R . . C4 C 0.2088(4) -0.3823(4) 0.3375(4) 0.0221(8) Uani 1 1 d . . . H4 H 0.2110 -0.3852 0.4206 0.027 Uiso 1 1 calc R . . C5 C 0.2005(4) -0.4932(4) 0.2422(4) 0.0227(8) Uani 1 1 d . . . H5 H 0.1958 -0.5722 0.2619 0.027 Uiso 1 1 calc R . . C6 C 0.2048(4) -0.3759(4) 0.1006(4) 0.0184(7) Uani 1 1 d . . . C7 C 0.2015(4) -0.3669(4) -0.0316(4) 0.0190(7) Uani 1 1 d . . . C8 C 0.1808(4) -0.2419(4) -0.1710(4) 0.0222(8) Uani 1 1 d . . . H8 H 0.1683 -0.1669 -0.1901 0.027 Uiso 1 1 calc R . . C9 C 0.1929(5) -0.3385(4) -0.2639(4) 0.0278(9) Uani 1 1 d . . . H9 H 0.1905 -0.3294 -0.3452 0.033 Uiso 1 1 calc R . . C10 C 0.2088(5) -0.4513(4) -0.2334(4) 0.0310(9) Uani 1 1 d . . . H10 H 0.2181 -0.5173 -0.2951 0.037 Uiso 1 1 calc R . . C11 C 0.3303(5) 0.1286(4) 0.0306(4) 0.0246(8) Uani 1 1 d . . . H11 H 0.4281 0.1242 0.0613 0.030 Uiso 1 1 calc R . . C12 C 0.3168(5) 0.2301(4) -0.0210(4) 0.0251(8) Uani 1 1 d . . . H12 H 0.4032 0.2929 -0.0267 0.030 Uiso 1 1 calc R . . C13 C 0.1704(4) 0.2343(4) -0.0636(4) 0.0216(8) Uani 1 1 d . . . H13 H 0.1576 0.3003 -0.0999 0.026 Uiso 1 1 calc R . . C14 C 0.0689(4) 0.0498(3) -0.0045(4) 0.0166(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U 0.01659(7) 0.01305(7) 0.01769(7) 0.00613(5) 0.00953(5) 0.00573(5) Cu 0.0222(2) 0.0155(2) 0.0183(2) 0.00793(19) 0.01020(18) 0.01060(18) O1 0.0206(12) 0.0187(12) 0.0189(13) 0.0062(11) 0.0079(11) 0.0092(10) O2 0.0181(12) 0.0219(13) 0.0167(13) 0.0071(11) 0.0075(10) 0.0072(10) O3 0.0205(12) 0.0129(11) 0.0199(13) 0.0059(11) 0.0109(11) 0.0060(10) O4 0.0202(12) 0.0126(11) 0.0240(14) 0.0069(11) 0.0126(11) 0.0053(10) O5 0.0267(13) 0.0130(12) 0.0245(14) 0.0057(11) 0.0176(12) 0.0064(10) O6 0.0233(13) 0.0150(12) 0.0270(14) 0.0063(11) 0.0172(12) 0.0061(10) O7 0.0169(12) 0.0157(12) 0.0198(13) 0.0038(11) 0.0090(10) 0.0070(10) O8 0.0264(14) 0.0319(16) 0.0237(15) 0.0005(13) 0.0095(12) 0.0133(13) O9 0.0214(13) 0.0386(16) 0.0216(15) 0.0063(13) 0.0075(12) 0.0135(12) O10 0.0249(14) 0.0406(16) 0.0285(15) 0.0170(14) 0.0146(12) 0.0206(13) N1 0.0176(14) 0.0168(14) 0.0164(15) 0.0063(12) 0.0075(12) 0.0099(12) N2 0.0202(14) 0.0179(14) 0.0170(15) 0.0062(13) 0.0093(13) 0.0075(12) N3 0.0361(18) 0.0237(17) 0.0256(18) 0.0109(15) 0.0170(16) 0.0178(15) N4 0.0249(16) 0.0191(15) 0.0211(17) 0.0094(14) 0.0072(13) 0.0112(13) N5 0.0193(14) 0.0191(15) 0.0193(16) 0.0080(13) 0.0106(13) 0.0102(12) N6 0.0202(14) 0.0139(14) 0.0161(15) 0.0056(12) 0.0076(12) 0.0089(12) N7 0.0202(15) 0.0245(16) 0.0210(17) 0.0126(14) 0.0096(13) 0.0092(13) C1 0.0161(16) 0.0171(17) 0.0187(18) 0.0078(15) 0.0076(14) 0.0076(14) C2 0.0188(16) 0.0168(16) 0.0203(18) 0.0076(15) 0.0121(14) 0.0072(14) C3 0.0199(17) 0.0207(18) 0.0194(18) 0.0074(16) 0.0091(15) 0.0111(15) C4 0.0245(18) 0.0269(19) 0.0186(19) 0.0133(17) 0.0101(16) 0.0132(16) C5 0.0222(18) 0.0230(18) 0.024(2) 0.0135(17) 0.0092(16) 0.0109(15) C6 0.0196(17) 0.0156(16) 0.0208(19) 0.0088(15) 0.0098(15) 0.0080(14) C7 0.0198(17) 0.0174(17) 0.0201(19) 0.0069(15) 0.0088(15) 0.0100(14) C8 0.0245(18) 0.0213(18) 0.0198(19) 0.0093(16) 0.0104(16) 0.0093(15) C9 0.036(2) 0.028(2) 0.024(2) 0.0133(18) 0.0185(18) 0.0144(18) C10 0.044(2) 0.031(2) 0.027(2) 0.0113(19) 0.023(2) 0.020(2) C11 0.0236(18) 0.0223(19) 0.030(2) 0.0111(18) 0.0141(17) 0.0115(16) C12 0.0276(19) 0.0206(18) 0.033(2) 0.0147(18) 0.0184(18) 0.0109(16) C13 0.0287(19) 0.0159(17) 0.0227(19) 0.0084(16) 0.0136(16) 0.0113(15) C14 0.0176(16) 0.0143(16) 0.0143(16) 0.0038(14) 0.0072(13) 0.0054(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U O2 1.768(2) . ? U O1 1.784(2) . ? U O7 2.239(2) . ? U O3 2.421(2) . ? U O4 2.421(2) 2_556 ? U O6 2.443(2) 2_666 ? U O5 2.464(2) . ? Cu O7 1.933(2) . ? Cu N1 2.005(3) . ? Cu N5 2.028(3) . ? Cu N2 2.039(3) . ? Cu N6 2.289(3) 2 ? O3 C1 1.254(4) . ? O4 C1 1.253(4) . ? O4 U 2.421(2) 2_556 ? O5 C2 1.253(4) . ? O6 C2 1.259(4) . ? O6 U 2.443(2) 2_666 ? O7 H7 0.8799 . ? O8 N7 1.260(4) . ? O9 N7 1.263(4) . ? O10 N7 1.249(4) . ? N1 C6 1.327(4) . ? N1 C3 1.339(4) . ? N2 C7 1.346(4) . ? N2 C8 1.356(4) . ? N3 C7 1.327(5) . ? N3 C10 1.341(5) . ? N4 C6 1.338(4) . ? N4 C5 1.344(5) . ? N5 C14 1.333(4) . ? N5 C11 1.335(4) . ? N6 C14 1.335(4) . ? N6 C13 1.346(4) . ? N6 Cu 2.289(3) 2 ? C1 C1 1.537(7) 2_556 ? C2 C2 1.544(7) 2_666 ? C3 C4 1.392(5) . ? C3 H3 0.9300 . ? C4 C5 1.370(5) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.494(5) . ? C8 C9 1.368(5) . ? C8 H8 0.9300 . ? C9 C10 1.397(6) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.387(5) . ? C11 H11 0.9300 . ? C12 C13 1.379(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C14 1.480(6) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 U O1 176.36(10) . . ? O2 U O7 89.73(10) . . ? O1 U O7 92.02(10) . . ? O2 U O3 95.42(9) . . ? O1 U O3 88.10(9) . . ? O7 U O3 75.88(8) . . ? O2 U O4 87.66(10) . 2_556 ? O1 U O4 92.89(10) . 2_556 ? O7 U O4 142.27(8) . 2_556 ? O3 U O4 66.93(8) . 2_556 ? O2 U O6 88.69(10) . 2_666 ? O1 U O6 87.94(10) . 2_666 ? O7 U O6 141.01(8) . 2_666 ? O3 U O6 143.02(8) . 2_666 ? O4 U O6 76.57(8) 2_556 2_666 ? O2 U O5 89.34(10) . . ? O1 U O5 88.03(10) . . ? O7 U O5 75.20(8) . . ? O3 U O5 150.65(8) . . ? O4 U O5 142.34(8) 2_556 . ? O6 U O5 65.83(8) 2_666 . ? O7 Cu N1 93.63(11) . . ? O7 Cu N5 90.84(11) . . ? N1 Cu N5 175.06(12) . . ? O7 Cu N2 159.48(11) . . ? N1 Cu N2 80.29(12) . . ? N5 Cu N2 96.21(12) . . ? O7 Cu N6 98.63(10) . 2 ? N1 Cu N6 99.94(10) . 2 ? N5 Cu N6 77.28(10) . 2 ? N2 Cu N6 101.71(11) . 2 ? C1 O3 U 119.7(2) . . ? C1 O4 U 119.4(2) . 2_556 ? C2 O5 U 120.0(2) . . ? C2 O6 U 120.5(2) . 2_666 ? Cu O7 U 138.78(12) . . ? Cu O7 H7 99.9 . . ? U O7 H7 119.9 . . ? C6 N1 C3 118.1(3) . . ? C6 N1 Cu 115.8(2) . . ? C3 N1 Cu 126.1(2) . . ? C7 N2 C8 116.7(3) . . ? C7 N2 Cu 113.9(2) . . ? C8 N2 Cu 128.5(2) . . ? C7 N3 C10 116.3(3) . . ? C6 N4 C5 114.8(3) . . ? C14 N5 C11 117.5(3) . . ? C14 N5 Cu 118.1(2) . . ? C11 N5 Cu 124.2(2) . . ? C14 N6 C13 116.8(3) . . ? C14 N6 Cu 109.8(2) . 2 ? C13 N6 Cu 133.3(2) . 2 ? O10 N7 O8 120.2(3) . . ? O10 N7 O9 119.7(3) . . ? O8 N7 O9 120.0(3) . . ? O4 C1 O3 126.3(3) . . ? O4 C1 C1 117.2(4) . 2_556 ? O3 C1 C1 116.5(3) . 2_556 ? O5 C2 O6 126.9(3) . . ? O5 C2 C2 116.6(3) . 2_666 ? O6 C2 C2 116.5(4) . 2_666 ? N1 C3 C4 119.6(3) . . ? N1 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.0(3) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? N4 C5 C4 123.0(3) . . ? N4 C5 H5 118.5 . . ? C4 C5 H5 118.5 . . ? N1 C6 N4 126.6(3) . . ? N1 C6 C7 114.9(3) . . ? N4 C6 C7 118.5(3) . . ? N3 C7 N2 126.4(3) . . ? N3 C7 C6 119.4(3) . . ? N2 C7 C6 114.2(3) . . ? N2 C8 C9 120.7(3) . . ? N2 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C10 118.2(4) . . ? C8 C9 H9 120.9 . . ? C10 C9 H9 120.9 . . ? N3 C10 C9 121.6(4) . . ? N3 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? N5 C11 C12 121.1(4) . . ? N5 C11 H11 119.4 . . ? C12 C11 H11 119.4 . . ? C13 C12 C11 117.5(3) . . ? C13 C12 H12 121.2 . . ? C11 C12 H12 121.2 . . ? N6 C13 C12 121.6(3) . . ? N6 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? N5 C14 N6 125.4(3) . . ? N5 C14 C14 117.7(4) . 2 ? N6 C14 C14 116.9(4) . 2 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O7 H7 O8 0.88 1.84 2.719(4) 175.0 . _database_code_depnum_ccdc_archive 'CCDC 929304' ####################################################################### # # 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 #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1363272479.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H8 Cu N2 O10 U' _chemical_formula_weight 665.79 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.3924(4) _cell_length_b 17.1982(14) _cell_length_c 11.9928(8) _cell_angle_alpha 90.00 _cell_angle_beta 108.319(4) _cell_angle_gamma 90.00 _cell_volume 1643.25(19) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 58102 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 30.51 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light green' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1228 _exptl_absorpt_coefficient_mu 11.200 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.428 _exptl_absorpt_correction_T_max 0.639 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and six \w scans with 2\% steps (459 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 58102 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 30.51 _reflns_number_total 5002 _reflns_number_gt 3552 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0200P)^2^] 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 5002 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0541 _refine_ls_goodness_of_fit_ref 0.950 _refine_ls_restrained_S_all 0.950 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.763 _refine_diff_density_min -1.286 _refine_diff_density_rms 0.191 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 U U 0.55151(2) 0.169993(10) 0.424782(14) 0.02189(6) Uani 1 1 d . . . Cu Cu 0.65429(7) 0.46459(3) 0.21311(5) 0.02580(13) Uani 1 1 d . . . O1 O 0.7186(4) 0.1403(2) 0.3746(3) 0.0320(8) Uani 1 1 d . . . O2 O 0.3819(4) 0.19980(19) 0.4718(3) 0.0283(7) Uani 1 1 d . . . O3 O 0.5514(4) 0.29294(18) 0.3346(3) 0.0274(7) Uani 1 1 d . . . O4 O 0.4630(4) 0.36711(19) 0.1719(3) 0.0307(8) Uani 1 1 d . . . O5 O 0.3562(4) 0.17986(18) 0.2285(3) 0.0299(8) Uani 1 1 d . . . O6 O 0.2188(4) 0.25428(19) 0.0801(3) 0.0341(8) Uani 1 1 d . . . O7 O 0.4330(4) 0.04338(18) 0.3622(3) 0.0277(7) Uani 1 1 d . . . O8 O 0.3914(4) -0.07681(18) 0.4162(2) 0.0250(7) Uani 1 1 d . . . O9 O 0.6814(4) 0.44486(18) 0.0586(3) 0.0278(7) Uani 1 1 d . . . O10 O 0.5293(4) 0.46653(18) -0.1292(3) 0.0263(7) Uani 1 1 d . . . N1 N 0.8366(4) 0.3960(2) 0.3039(3) 0.0246(8) Uani 1 1 d . . . N2 N 0.6757(4) 0.5064(2) 0.3692(3) 0.0266(9) Uani 1 1 d . . . C1 C 0.4590(5) 0.3086(3) 0.2288(4) 0.0250(10) Uani 1 1 d . . . C2 C 0.3333(5) 0.2432(3) 0.1733(4) 0.0255(11) Uani 1 1 d . . . C3 C 0.4487(5) -0.0095(3) 0.4357(4) 0.0226(9) Uani 1 1 d . . . C4 C 0.5607(5) 0.4745(3) -0.0203(4) 0.0245(10) Uani 1 1 d . . . C5 C 0.9041(6) 0.3382(3) 0.2587(4) 0.0297(11) Uani 1 1 d . . . H5 H 0.8789 0.3342 0.1776 0.036 Uiso 1 1 calc R . . C6 C 1.0111(6) 0.2839(3) 0.3308(5) 0.0349(12) Uani 1 1 d . . . H6 H 1.0571 0.2438 0.2987 0.042 Uiso 1 1 calc R . . C7 C 1.0478(6) 0.2906(3) 0.4513(4) 0.0342(12) Uani 1 1 d . . . H7 H 1.1164 0.2541 0.5009 0.041 Uiso 1 1 calc R . . C8 C 0.9822(5) 0.3517(3) 0.4973(4) 0.0277(11) Uani 1 1 d . . . H8 H 1.0114 0.3584 0.5782 0.033 Uiso 1 1 calc R . . C9 C 0.8718(5) 0.4030(3) 0.4214(4) 0.0242(10) Uani 1 1 d . . . C10 C 0.7843(5) 0.4675(3) 0.4600(4) 0.0248(10) Uani 1 1 d . . . C11 C 0.8043(6) 0.4868(3) 0.5753(4) 0.0277(10) Uani 1 1 d . . . H11 H 0.8771 0.4584 0.6362 0.033 Uiso 1 1 calc R . . C12 C 0.7159(6) 0.5485(3) 0.5996(4) 0.0318(12) Uani 1 1 d . . . H12 H 0.7294 0.5624 0.6769 0.038 Uiso 1 1 calc R . . C13 C 0.6061(6) 0.5897(3) 0.5075(4) 0.0313(11) Uani 1 1 d . . . H13 H 0.5463 0.6320 0.5220 0.038 Uiso 1 1 calc R . . C14 C 0.5880(6) 0.5663(3) 0.3933(4) 0.0288(11) Uani 1 1 d . . . H14 H 0.5128 0.5928 0.3313 0.035 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U 0.02437(9) 0.02075(9) 0.01926(8) 0.00041(7) 0.00501(6) 0.00027(8) Cu 0.0266(3) 0.0299(3) 0.0200(3) 0.0012(2) 0.0061(2) 0.0039(2) O1 0.0324(17) 0.0296(18) 0.0396(19) 0.0030(16) 0.0192(15) 0.0037(15) O2 0.0262(16) 0.0289(18) 0.0314(18) 0.0004(15) 0.0114(14) 0.0045(14) O3 0.0333(17) 0.0229(17) 0.0227(17) 0.0010(14) 0.0040(14) -0.0038(14) O4 0.0335(18) 0.0272(18) 0.0281(17) 0.0079(15) 0.0051(14) 0.0000(15) O5 0.0391(18) 0.0265(18) 0.0180(15) -0.0021(14) 0.0003(13) -0.0032(15) O6 0.0397(19) 0.0276(18) 0.0253(18) 0.0011(14) -0.0034(15) 0.0073(15) O7 0.0351(17) 0.0225(17) 0.0211(16) 0.0010(14) 0.0024(13) -0.0039(14) O8 0.0289(17) 0.0219(17) 0.0199(16) 0.0013(13) 0.0014(13) -0.0025(13) O9 0.0274(16) 0.0302(19) 0.0249(17) 0.0021(14) 0.0071(14) 0.0053(14) O10 0.0280(16) 0.0300(18) 0.0206(16) 0.0009(14) 0.0071(13) 0.0026(14) N1 0.0215(18) 0.032(2) 0.0214(19) -0.0004(17) 0.0079(15) -0.0014(17) N2 0.0265(19) 0.026(2) 0.026(2) 0.0004(17) 0.0064(16) 0.0008(17) C1 0.028(2) 0.024(2) 0.024(2) 0.0018(19) 0.0098(19) 0.0040(19) C2 0.030(3) 0.025(3) 0.018(2) 0.0046(19) 0.0016(19) 0.006(2) C3 0.027(2) 0.018(2) 0.023(2) 0.0021(19) 0.0072(18) 0.0005(19) C4 0.030(2) 0.017(2) 0.028(2) 0.003(2) 0.0111(19) -0.0029(19) C5 0.027(2) 0.033(3) 0.031(3) -0.001(2) 0.012(2) -0.001(2) C6 0.032(3) 0.033(3) 0.041(3) -0.003(2) 0.013(2) 0.005(2) C7 0.029(3) 0.039(3) 0.035(3) 0.006(2) 0.011(2) 0.010(2) C8 0.024(2) 0.037(3) 0.023(2) 0.006(2) 0.0082(19) 0.003(2) C9 0.019(2) 0.029(3) 0.025(2) 0.000(2) 0.0074(18) -0.0027(19) C10 0.021(2) 0.027(3) 0.024(2) -0.001(2) 0.0039(18) -0.0042(19) C11 0.030(2) 0.031(3) 0.023(2) 0.001(2) 0.0089(19) -0.002(2) C12 0.034(3) 0.039(3) 0.024(3) -0.008(2) 0.011(2) -0.009(2) C13 0.037(3) 0.024(3) 0.034(3) -0.007(2) 0.013(2) -0.001(2) C14 0.026(2) 0.030(3) 0.027(3) 0.002(2) 0.0036(19) 0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U O2 1.764(3) . ? U O1 1.766(3) . ? U O6 2.344(3) 4_666 ? U O3 2.375(3) . ? U O7 2.413(3) . ? U O5 2.415(3) . ? U O8 2.421(3) 3_656 ? Cu O10 1.953(3) 3_665 ? Cu N2 1.960(4) . ? Cu O9 1.966(3) . ? Cu N1 1.967(4) . ? Cu O4 2.265(3) . ? O3 C1 1.290(5) . ? O4 C1 1.222(5) . ? O5 C2 1.257(5) . ? O6 C2 1.238(5) . ? O6 U 2.344(3) 4_565 ? O7 C3 1.244(5) . ? O8 C3 1.246(5) . ? O8 U 2.421(3) 3_656 ? O9 C4 1.256(5) . ? O10 C4 1.257(5) . ? O10 Cu 1.953(3) 3_665 ? N1 C5 1.340(6) . ? N1 C9 1.352(5) . ? N2 C14 1.349(6) . ? N2 C10 1.356(5) . ? C1 C2 1.542(6) . ? C3 C3 1.548(8) 3_656 ? C4 C4 1.534(9) 3_665 ? C5 C6 1.393(7) . ? C5 H5 0.9300 . ? C6 C7 1.384(7) . ? C6 H6 0.9300 . ? C7 C8 1.379(7) . ? C7 H7 0.9300 . ? C8 C9 1.391(6) . ? C8 H8 0.9300 . ? C9 C10 1.483(6) . ? C10 C11 1.380(6) . ? C11 C12 1.377(7) . ? C11 H11 0.9300 . ? C12 C13 1.389(6) . ? C12 H12 0.9300 . ? C13 C14 1.389(7) . ? C13 H13 0.9300 . ? C14 H14 0.9300 . ? 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 U O1 178.80(14) . . ? O2 U O6 85.78(13) . 4_666 ? O1 U O6 95.15(14) . 4_666 ? O2 U O3 90.11(13) . . ? O1 U O3 89.35(13) . . ? O6 U O3 77.40(10) 4_666 . ? O2 U O7 93.82(13) . . ? O1 U O7 85.83(13) . . ? O6 U O7 146.48(11) 4_666 . ? O3 U O7 136.10(10) . . ? O2 U O5 85.56(13) . . ? O1 U O5 93.24(13) . . ? O6 U O5 142.12(11) 4_666 . ? O3 U O5 65.82(10) . . ? O7 U O5 70.93(10) . . ? O2 U O8 85.43(13) . 3_656 ? O1 U O8 95.48(13) . 3_656 ? O6 U O8 79.68(11) 4_666 3_656 ? O3 U O8 156.91(10) . 3_656 ? O7 U O8 66.91(9) . 3_656 ? O5 U O8 136.06(10) . 3_656 ? O10 Cu N2 95.18(14) 3_665 . ? O10 Cu O9 85.72(12) 3_665 . ? N2 Cu O9 163.82(15) . . ? O10 Cu N1 177.51(15) 3_665 . ? N2 Cu N1 82.50(15) . . ? O9 Cu N1 96.77(14) . . ? O10 Cu O4 86.93(12) 3_665 . ? N2 Cu O4 109.00(14) . . ? O9 Cu O4 87.17(12) . . ? N1 Cu O4 92.95(13) . . ? C1 O3 U 123.2(3) . . ? C1 O4 Cu 129.0(3) . . ? C2 O5 U 121.2(3) . . ? C2 O6 U 154.7(3) . 4_565 ? C3 O7 U 119.9(3) . . ? C3 O8 U 119.8(3) . 3_656 ? C4 O9 Cu 109.6(3) . . ? C4 O10 Cu 110.1(3) . 3_665 ? C5 N1 C9 120.4(4) . . ? C5 N1 Cu 125.1(3) . . ? C9 N1 Cu 113.6(3) . . ? C14 N2 C10 118.6(4) . . ? C14 N2 Cu 126.3(3) . . ? C10 N2 Cu 115.0(3) . . ? O4 C1 O3 127.4(4) . . ? O4 C1 C2 119.7(4) . . ? O3 C1 C2 113.0(4) . . ? O6 C2 O5 123.7(4) . . ? O6 C2 C1 120.5(4) . . ? O5 C2 C1 115.7(4) . . ? O8 C3 O7 126.7(4) . . ? O8 C3 C3 116.4(5) . 3_656 ? O7 C3 C3 116.9(5) . 3_656 ? O9 C4 O10 126.5(4) . . ? O9 C4 C4 116.9(5) . 3_665 ? O10 C4 C4 116.7(5) . 3_665 ? N1 C5 C6 121.2(5) . . ? N1 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C7 C6 C5 118.7(5) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C8 C7 C6 119.7(4) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C7 C8 C9 119.2(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? N1 C9 C8 120.6(4) . . ? N1 C9 C10 115.1(4) . . ? C8 C9 C10 124.3(4) . . ? N2 C10 C11 121.7(4) . . ? N2 C10 C9 113.1(4) . . ? C11 C10 C9 125.2(4) . . ? C12 C11 C10 119.5(4) . . ? C12 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? C11 C12 C13 119.5(4) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C12 C13 C14 118.3(5) . . ? C12 C13 H13 120.8 . . ? C14 C13 H13 120.8 . . ? N2 C14 C13 122.3(4) . . ? N2 C14 H14 118.8 . . ? C13 C14 H14 118.8 . . ? _database_code_depnum_ccdc_archive 'CCDC 929305' ####################################################################### # # 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_5 #TrackingRef 'web_deposit_cif_file_0_P.Thuery_1363272479.CIF.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H8 Cu N2 O10 U' _chemical_formula_weight 689.81 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.8103(6) _cell_length_b 16.5690(7) _cell_length_c 12.5158(7) _cell_angle_alpha 90.00 _cell_angle_beta 107.188(3) _cell_angle_gamma 90.00 _cell_volume 1745.44(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 48655 _cell_measurement_theta_min 2.10 _cell_measurement_theta_max 30.50 _exptl_crystal_description platelet _exptl_crystal_colour 'translucent light green' _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.625 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1276 _exptl_absorpt_coefficient_mu 10.549 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.422 _exptl_absorpt_correction_T_max 0.729 _exptl_absorpt_process_details 'SCALEPACK (Otwinowski & Minor, 1997)' _exptl_special_details 'crystal-to-detector distance 30 mm' _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD area-detector diffractometer' _diffrn_measurement_method 'two \f and three \w scans with 2\% steps (356 frames)' _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 48655 _diffrn_reflns_av_R_equivalents 0.0746 _diffrn_reflns_av_sigmaI/netI 0.0963 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 30.50 _reflns_number_total 5335 _reflns_number_gt 3674 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1998)' _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 'SHELXTL (Sheldrick, 2008); PLATON (Spek, 2003)' _refine_special_details ; Structure solved by direct methods and subsequent Fourier-difference synthesis. All non-hydrogen atoms were refined with anisotropic displacement parameters. The H atoms were introduced at calculated positions and were treated as riding atoms with an isotropic displacement parameter equal to 1.2 times that of the parent atom. 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^)+(0.0082P)^2^] 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 5335 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0588 _refine_ls_wR_factor_gt 0.0532 _refine_ls_goodness_of_fit_ref 0.940 _refine_ls_restrained_S_all 0.940 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.087 _refine_diff_density_min -1.555 _refine_diff_density_rms 0.210 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 U U 0.41633(2) 0.679516(11) 0.928769(13) 0.01830(5) Uani 1 1 d . . . Cu Cu 0.08077(8) 0.95031(4) 0.70284(4) 0.02464(15) Uani 1 1 d . . . O1 O 0.6189(4) 0.7072(2) 0.9766(2) 0.0252(8) Uani 1 1 d . . . O2 O 0.2136(4) 0.6509(2) 0.8805(2) 0.0263(8) Uani 1 1 d . . . O3 O 0.3376(4) 0.80271(19) 0.8304(2) 0.0233(8) Uani 1 1 d . . . O4 O 0.2260(4) 0.8557(2) 0.6600(3) 0.0289(9) Uani 1 1 d . . . O5 O 0.4500(4) 0.6827(2) 0.7439(2) 0.0237(8) Uani 1 1 d . . . O6 O 0.3872(4) 0.7402(2) 0.5760(2) 0.0256(8) Uani 1 1 d . . . O7 O 0.4678(4) 0.54568(19) 0.8705(2) 0.0233(8) Uani 1 1 d . . . O8 O 0.5161(4) 0.4162(2) 0.9199(2) 0.0240(8) Uani 1 1 d . . . O9 O -0.0899(4) 0.9286(2) 0.5635(3) 0.0280(8) Uani 1 1 d . . . O10 O -0.1500(4) 0.9663(2) 0.3830(3) 0.0283(8) Uani 1 1 d . . . N1 N -0.0105(5) 0.8791(2) 0.7942(3) 0.0227(9) Uani 1 1 d . . . N2 N 0.2021(5) 0.9955(2) 0.8499(3) 0.0238(10) Uani 1 1 d . . . C1 C 0.3080(6) 0.8068(3) 0.7253(4) 0.0211(11) Uani 1 1 d . . . C2 C 0.3898(6) 0.7383(3) 0.6762(3) 0.0208(11) Uani 1 1 d . . . C3 C 0.4949(6) 0.4893(3) 0.9387(3) 0.0230(11) Uani 1 1 d . . . C4 C -0.0700(6) 0.9695(3) 0.4846(4) 0.0269(12) Uani 1 1 d . . . C5 C -0.1109(6) 0.8167(3) 0.7634(4) 0.0287(12) Uani 1 1 d . . . H5 H -0.1583 0.8074 0.6875 0.034 Uiso 1 1 calc R . . C6 C -0.1462(6) 0.7662(3) 0.8391(4) 0.0307(13) Uani 1 1 d . . . H6 H -0.2143 0.7228 0.8138 0.037 Uiso 1 1 calc R . . C7 C -0.0826(6) 0.7788(3) 0.9515(4) 0.0268(12) Uani 1 1 d . . . H7 H -0.1043 0.7436 1.0030 0.032 Uiso 1 1 calc R . . C8 C 0.0170(6) 0.8466(3) 0.9876(4) 0.0223(11) Uani 1 1 d . . . C9 C 0.0547(6) 0.8925(3) 0.9055(4) 0.0205(11) Uani 1 1 d . . . C10 C 0.1653(6) 0.9579(3) 0.9363(4) 0.0225(11) Uani 1 1 d . . . C11 C 0.2289(6) 0.9800(3) 1.0491(4) 0.0255(12) Uani 1 1 d . . . C12 C 0.1818(6) 0.9354(3) 1.1297(4) 0.0271(12) Uani 1 1 d . . . H12 H 0.2205 0.9505 1.2045 0.033 Uiso 1 1 calc R . . C13 C 0.0819(6) 0.8712(3) 1.1024(4) 0.0281(13) Uani 1 1 d . . . H13 H 0.0551 0.8429 1.1584 0.034 Uiso 1 1 calc R . . C14 C 0.3387(6) 1.0441(3) 1.0707(4) 0.0313(13) Uani 1 1 d . . . H14 H 0.3860 1.0608 1.1440 0.038 Uiso 1 1 calc R . . C15 C 0.3757(6) 1.0818(3) 0.9853(4) 0.0319(13) Uani 1 1 d . . . H15 H 0.4467 1.1248 0.9999 0.038 Uiso 1 1 calc R . . C16 C 0.3070(6) 1.0557(3) 0.8754(4) 0.0283(12) Uani 1 1 d . . . H16 H 0.3355 1.0813 0.8180 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U 0.02348(10) 0.01709(10) 0.01495(8) 0.00059(8) 0.00664(6) 0.00120(9) Cu 0.0274(4) 0.0240(4) 0.0223(3) 0.0047(3) 0.0070(3) -0.0017(3) O1 0.021(2) 0.035(2) 0.0190(15) -0.0020(15) 0.0053(14) -0.0050(17) O2 0.028(2) 0.033(2) 0.0184(15) -0.0045(15) 0.0076(14) -0.0055(17) O3 0.035(2) 0.0173(18) 0.0170(15) 0.0028(14) 0.0065(14) 0.0072(16) O4 0.037(2) 0.029(2) 0.0225(16) 0.0113(16) 0.0127(16) 0.0081(18) O5 0.031(2) 0.0235(19) 0.0185(14) 0.0003(15) 0.0112(14) 0.0024(17) O6 0.038(2) 0.0234(19) 0.0161(15) 0.0003(15) 0.0095(15) -0.0035(17) O7 0.038(2) 0.0156(19) 0.0175(15) 0.0068(14) 0.0106(15) 0.0067(16) O8 0.043(2) 0.0148(18) 0.0167(15) 0.0006(14) 0.0124(15) 0.0060(16) O9 0.031(2) 0.028(2) 0.0254(17) 0.0084(16) 0.0084(15) -0.0067(17) O10 0.025(2) 0.031(2) 0.0255(17) 0.0069(16) 0.0033(16) -0.0053(17) N1 0.026(2) 0.022(2) 0.0208(19) 0.0039(18) 0.0068(18) -0.0007(19) N2 0.022(2) 0.021(2) 0.030(2) 0.0024(19) 0.0096(19) 0.0054(19) C1 0.022(3) 0.018(3) 0.024(2) -0.001(2) 0.009(2) -0.004(2) C2 0.026(3) 0.024(3) 0.013(2) 0.003(2) 0.007(2) -0.009(2) C3 0.025(3) 0.026(3) 0.018(2) -0.002(2) 0.007(2) -0.002(2) C4 0.025(3) 0.028(3) 0.028(3) 0.007(2) 0.010(2) 0.005(2) C5 0.028(3) 0.029(3) 0.030(2) -0.004(2) 0.010(2) -0.003(3) C6 0.034(3) 0.027(3) 0.034(3) 0.002(2) 0.014(2) -0.007(3) C7 0.031(3) 0.026(3) 0.029(3) 0.006(2) 0.016(2) 0.004(3) C8 0.019(3) 0.023(3) 0.027(2) -0.001(2) 0.008(2) 0.007(2) C9 0.023(3) 0.019(3) 0.020(2) 0.000(2) 0.007(2) 0.004(2) C10 0.020(3) 0.024(3) 0.023(2) 0.001(2) 0.006(2) 0.010(2) C11 0.022(3) 0.022(3) 0.029(3) -0.003(2) 0.003(2) 0.005(2) C12 0.031(3) 0.029(3) 0.017(2) -0.004(2) 0.001(2) 0.010(3) C13 0.027(3) 0.039(3) 0.018(2) 0.006(2) 0.006(2) 0.013(3) C14 0.028(3) 0.032(3) 0.030(3) -0.003(3) 0.002(2) 0.009(3) C15 0.027(3) 0.021(3) 0.041(3) -0.008(3) 0.001(2) -0.001(2) C16 0.025(3) 0.022(3) 0.040(3) 0.009(2) 0.013(2) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U O1 1.767(3) . ? U O2 1.773(3) . ? U O6 2.347(3) 4_576 ? U O3 2.379(3) . ? U O8 2.407(3) 3_667 ? U O7 2.419(3) . ? U O5 2.419(3) . ? Cu O10 1.955(3) 3_576 ? Cu O9 1.970(3) . ? Cu N1 1.972(4) . ? Cu N2 1.982(4) . ? Cu O4 2.187(4) . ? O3 C1 1.265(5) . ? O4 C1 1.224(5) . ? O5 C2 1.258(5) . ? O6 C2 1.249(5) . ? O6 U 2.347(3) 4_575 ? O7 C3 1.239(5) . ? O8 C3 1.258(6) . ? O8 U 2.407(3) 3_667 ? O9 C4 1.252(5) . ? O10 C4 1.259(5) . ? O10 Cu 1.955(3) 3_576 ? N1 C5 1.342(6) . ? N1 C9 1.358(5) . ? N2 C16 1.333(6) . ? N2 C10 1.368(6) . ? C1 C2 1.563(6) . ? C3 C3 1.552(8) 3_667 ? C4 C4 1.553(10) 3_576 ? C5 C6 1.367(6) . ? C5 H5 0.9300 . ? C6 C7 1.369(6) . ? C6 H6 0.9300 . ? C7 C8 1.415(7) . ? C7 H7 0.9300 . ? C8 C9 1.396(6) . ? C8 C13 1.439(6) . ? C9 C10 1.431(7) . ? C10 C11 1.405(6) . ? C11 C12 1.408(7) . ? C11 C14 1.408(7) . ? C12 C13 1.358(7) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 C15 1.359(7) . ? C14 H14 0.9300 . ? C15 C16 1.397(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 U O2 179.50(16) . . ? O1 U O6 85.45(13) . 4_576 ? O2 U O6 94.95(13) . 4_576 ? O1 U O3 93.61(14) . . ? O2 U O3 86.75(14) . . ? O6 U O3 80.64(10) 4_576 . ? O1 U O8 85.10(14) . 3_667 ? O2 U O8 94.68(14) . 3_667 ? O6 U O8 79.32(11) 4_576 3_667 ? O3 U O8 159.96(10) . 3_667 ? O1 U O7 94.58(14) . . ? O2 U O7 84.92(15) . . ? O6 U O7 146.09(10) 4_576 . ? O3 U O7 133.05(10) . . ? O8 U O7 66.93(9) 3_667 . ? O1 U O5 85.48(12) . . ? O2 U O5 94.36(12) . . ? O6 U O5 144.22(11) 4_576 . ? O3 U O5 65.50(10) . . ? O8 U O5 134.08(11) 3_667 . ? O7 U O5 69.20(10) . . ? O10 Cu O9 85.57(13) 3_576 . ? O10 Cu N1 171.20(16) 3_576 . ? O9 Cu N1 93.95(15) . . ? O10 Cu N2 94.20(15) 3_576 . ? O9 Cu N2 162.21(16) . . ? N1 Cu N2 83.56(16) . . ? O10 Cu O4 94.09(14) 3_576 . ? O9 Cu O4 90.04(14) . . ? N1 Cu O4 94.70(15) . . ? N2 Cu O4 107.71(15) . . ? C1 O3 U 121.5(3) . . ? C1 O4 Cu 125.7(3) . . ? C2 O5 U 120.9(3) . . ? C2 O6 U 146.0(3) . 4_575 ? C3 O7 U 119.9(3) . . ? C3 O8 U 120.2(3) . 3_667 ? C4 O9 Cu 110.5(3) . . ? C4 O10 Cu 110.7(3) . 3_576 ? C5 N1 C9 117.7(4) . . ? C5 N1 Cu 129.9(3) . . ? C9 N1 Cu 112.0(3) . . ? C16 N2 C10 117.4(4) . . ? C16 N2 Cu 130.6(3) . . ? C10 N2 Cu 111.9(3) . . ? O4 C1 O3 129.0(5) . . ? O4 C1 C2 117.9(4) . . ? O3 C1 C2 113.1(4) . . ? O6 C2 O5 125.0(5) . . ? O6 C2 C1 120.2(4) . . ? O5 C2 C1 114.8(4) . . ? O7 C3 O8 127.3(4) . . ? O7 C3 C3 116.9(5) . 3_667 ? O8 C3 C3 115.8(5) . 3_667 ? O9 C4 O10 127.3(5) . . ? O9 C4 C4 116.3(5) . 3_576 ? O10 C4 C4 116.4(5) . 3_576 ? N1 C5 C6 122.5(5) . . ? N1 C5 H5 118.7 . . ? C6 C5 H5 118.7 . . ? C5 C6 C7 120.8(5) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C8 118.4(5) . . ? C6 C7 H7 120.8 . . ? C8 C7 H7 120.8 . . ? C9 C8 C7 117.3(4) . . ? C9 C8 C13 118.0(5) . . ? C7 C8 C13 124.8(5) . . ? N1 C9 C8 123.0(5) . . ? N1 C9 C10 116.6(4) . . ? C8 C9 C10 120.4(4) . . ? N2 C10 C11 124.0(5) . . ? N2 C10 C9 115.7(4) . . ? C11 C10 C9 120.3(4) . . ? C10 C11 C12 118.0(5) . . ? C10 C11 C14 115.9(5) . . ? C12 C11 C14 126.1(5) . . ? C13 C12 C11 122.4(4) . . ? C13 C12 H12 118.8 . . ? C11 C12 H12 118.8 . . ? C12 C13 C8 120.7(5) . . ? C12 C13 H13 119.6 . . ? C8 C13 H13 119.6 . . ? C15 C14 C11 120.4(5) . . ? C15 C14 H14 119.8 . . ? C11 C14 H14 119.8 . . ? C14 C15 C16 119.9(5) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? N2 C16 C15 122.4(5) . . ? N2 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? _database_code_depnum_ccdc_archive 'CCDC 929306'