# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Bin Zhang' _publ_contact_author_email zhangbin@iccas.ac.cn loop_ _publ_author_name 'Bin Zhang' 'Yan Zhang' 'Daoben Zhu' data_135K _database_code_depnum_ccdc_archive 'CCDC 852903' #TrackingRef '- CCDC852903.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H32 Cu2 N2 O12' _chemical_formula_weight 595.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.69870(10) _cell_length_b 34.1408(4) _cell_length_c 8.60810(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.5780(10) _cell_angle_gamma 90.00 _cell_volume 2437.07(5) _cell_formula_units_Z 4 _cell_measurement_temperature 135(2) _cell_measurement_reflns_used 34980 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description diamondiod _exptl_crystal_colour blue _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.623 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.808 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.584 _exptl_absorpt_correction_T_max 0.680 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 135(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 KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27882 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.54 _reflns_number_total 5518 _reflns_number_gt 4832 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0329P)^2^+2.1556P] 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 SHELXL _refine_ls_extinction_coef 0.0026(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5518 _refine_ls_number_parameters 319 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0823 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.101 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.74864(3) 0.203472(7) 0.48079(3) 0.01719(9) Uani 1 1 d . . . Cu2 Cu 0.73785(3) 0.045530(7) 0.49830(3) 0.01667(9) Uani 1 1 d . . . O1 O 0.89567(17) 0.15350(4) 0.61059(17) 0.0193(3) Uani 1 1 d . . . O2 O 0.84818(17) 0.08995(4) 0.62829(16) 0.0196(3) Uani 1 1 d . . . O3 O 0.62075(18) 0.16010(4) 0.35884(17) 0.0224(3) Uani 1 1 d . . . O4 O 0.61147(18) 0.09516(4) 0.33753(17) 0.0222(3) Uani 1 1 d . . . O5 O 0.62359(18) 0.20581(4) 0.64185(17) 0.0211(3) Uani 1 1 d . . . O6 O 0.58664(19) 0.24810(5) 0.82434(19) 0.0263(3) Uani 1 1 d . . . O7 O 0.87410(18) 0.24625(4) 0.61530(18) 0.0222(3) Uani 1 1 d . . . O8 O 0.85791(18) 0.28752(4) 0.80976(17) 0.0223(3) Uani 1 1 d . . . O9 O 0.90589(17) 0.04080(4) 0.38507(17) 0.0196(3) Uani 1 1 d . . . O10 O 1.08851(19) 0.00016(4) 0.34265(18) 0.0242(3) Uani 1 1 d . . . O11 O 0.56971(18) 0.04222(4) 0.61269(17) 0.0203(3) Uani 1 1 d . . . O12 O 0.37848(18) 0.00003(4) 0.62778(17) 0.0213(3) Uani 1 1 d . . . C1 C 0.8178(2) 0.12323(6) 0.5622(2) 0.0159(4) Uani 1 1 d . . . C2 C 0.6695(2) 0.12595(6) 0.4053(2) 0.0173(4) Uani 1 1 d . . . C3 C 0.8104(2) 0.25863(6) 0.7193(2) 0.0180(4) Uani 1 1 d . . . C4 C 0.6600(2) 0.23616(6) 0.7323(2) 0.0186(4) Uani 1 1 d . . . C5 C 0.9999(2) 0.01136(6) 0.4211(2) 0.0175(4) Uani 1 1 d . . . C6 C 0.4849(2) 0.01226(6) 0.5695(2) 0.0174(4) Uani 1 1 d . . . N1 N 0.8972(2) 0.08001(5) 0.0983(2) 0.0255(4) Uani 1 1 d . . . H1 H 0.9125 0.0671 0.1970 0.031 Uiso 1 1 calc R . . C7 C 0.9018(3) 0.12313(7) 0.1360(3) 0.0316(5) Uani 1 1 d . . . H7A H 1.0012 0.1288 0.2259 0.038 Uiso 1 1 calc R . . H7B H 0.8087 0.1296 0.1748 0.038 Uiso 1 1 calc R . . C8 C 0.8976(4) 0.14930(7) -0.0067(3) 0.0366(6) Uani 1 1 d . . . H8A H 0.8914 0.1767 0.0244 0.055 Uiso 1 1 calc R . . H8B H 0.8029 0.1429 -0.0988 0.055 Uiso 1 1 calc R . . H8C H 0.9956 0.1453 -0.0382 0.055 Uiso 1 1 calc R . . C9 C 1.0301(3) 0.06663(7) 0.0337(3) 0.0317(5) Uani 1 1 d . . . H9A H 1.0139 0.0783 -0.0753 0.038 Uiso 1 1 calc R . . H9B H 1.0239 0.0378 0.0205 0.038 Uiso 1 1 calc R . . C10 C 1.1955(3) 0.07746(8) 0.1422(4) 0.0449(7) Uani 1 1 d . . . H10A H 1.2766 0.0695 0.0903 0.067 Uiso 1 1 calc R . . H10B H 1.2164 0.0641 0.2473 0.067 Uiso 1 1 calc R . . H10C H 1.2014 0.1059 0.1596 0.067 Uiso 1 1 calc R . . C11 C 0.7332(3) 0.06829(8) -0.0084(3) 0.0346(6) Uani 1 1 d . . . H11C H 0.6505 0.0811 0.0319 0.041 Uiso 1 1 calc R . . H11D H 0.7190 0.0778 -0.1204 0.041 Uiso 1 1 calc R . . C12 C 0.7065(4) 0.02501(9) -0.0133(3) 0.0480(7) Uani 1 1 d . . . H12D H 0.6112 0.0185 -0.1046 0.072 Uiso 1 1 calc R . . H12E H 0.6897 0.0164 0.0890 0.072 Uiso 1 1 calc R . . H12F H 0.8012 0.0117 -0.0276 0.072 Uiso 1 1 calc R . . N2 N 0.3394(2) 0.17095(6) 0.6497(2) 0.0259(4) Uani 1 1 d . B . H2 H 0.4340 0.1846 0.6574 0.031 Uiso 1 1 calc R . . C13 C 0.2936(3) 0.18127(8) 0.7986(3) 0.0342(6) Uani 1 1 d . . . H13A H 0.1892 0.1687 0.7918 0.041 Uiso 1 1 calc R . . H13B H 0.2787 0.2100 0.8013 0.041 Uiso 1 1 calc R . . C14 C 0.4176(4) 0.16865(11) 0.9551(3) 0.0588(9) Uani 1 1 d . . . H14A H 0.3793 0.1753 1.0479 0.088 Uiso 1 1 calc R . . H14B H 0.5197 0.1822 0.9661 0.088 Uiso 1 1 calc R . . H14C H 0.4343 0.1403 0.9528 0.088 Uiso 1 1 calc R . . C15 C 0.3770(3) 0.12858(7) 0.6368(4) 0.0410(6) Uani 1 1 d . . . H15A H 0.4730 0.1218 0.7289 0.049 Uiso 1 1 calc R . . H15B H 0.4052 0.1245 0.5349 0.049 Uiso 1 1 calc R . . C16 C 0.2416(3) 0.10088(8) 0.6376(4) 0.0474(8) Uani 1 1 d . . . H16A H 0.2755 0.0739 0.6279 0.071 Uiso 1 1 calc R . . H16B H 0.1464 0.1070 0.5456 0.071 Uiso 1 1 calc R . . H16C H 0.2151 0.1039 0.7399 0.071 Uiso 1 1 calc R . . C17 C 0.2149(4) 0.18636(10) 0.5010(3) 0.0480(8) Uani 1 1 d . . . H17A H 0.1228 0.1679 0.4750 0.058 Uiso 0.70(4) 1 calc PR A 1 H17B H 0.1754 0.2115 0.5316 0.058 Uiso 0.70(4) 1 calc PR A 1 H17C H 0.2130 0.1687 0.4095 0.058 Uiso 0.30(4) 1 d PR A 2 H17D H 0.1085 0.1844 0.5190 0.058 Uiso 0.30(4) 1 d PR A 2 C181 C 0.2544(5) 0.19291(13) 0.3549(5) 0.0345(12) Uani 0.614(7) 1 d P B 1 H18A H 0.1595 0.2030 0.2710 0.052 Uiso 0.614(7) 1 calc PR B 1 H18B H 0.2888 0.1682 0.3177 0.052 Uiso 0.614(7) 1 calc PR B 1 H18C H 0.3421 0.2121 0.3749 0.052 Uiso 0.614(7) 1 calc PR B 1 C182 C 0.2338(8) 0.2235(2) 0.4564(10) 0.050(3) Uani 0.386(7) 1 d P B 2 H18D H 0.1451 0.2302 0.3590 0.075 Uiso 0.386(7) 1 calc PR B 2 H18E H 0.3366 0.2258 0.4323 0.075 Uiso 0.386(7) 1 calc PR B 2 H18F H 0.2333 0.2414 0.5453 0.075 Uiso 0.386(7) 1 calc PR B 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02009(15) 0.01345(14) 0.01895(13) -0.00042(9) 0.00728(10) -0.00098(9) Cu2 0.01856(14) 0.01347(14) 0.01885(13) -0.00044(8) 0.00697(10) -0.00190(9) O1 0.0202(7) 0.0152(7) 0.0215(7) -0.0007(5) 0.0050(6) -0.0039(6) O2 0.0213(7) 0.0165(7) 0.0193(7) 0.0021(5) 0.0034(6) -0.0014(6) O3 0.0248(8) 0.0169(7) 0.0215(7) -0.0004(6) 0.0010(6) 0.0020(6) O4 0.0240(8) 0.0172(7) 0.0223(7) -0.0025(6) 0.0024(6) -0.0025(6) O5 0.0213(8) 0.0192(7) 0.0242(7) -0.0034(6) 0.0092(6) -0.0053(6) O6 0.0256(8) 0.0270(8) 0.0308(8) -0.0059(6) 0.0152(7) -0.0028(7) O7 0.0229(8) 0.0204(7) 0.0263(7) -0.0034(6) 0.0120(6) -0.0056(6) O8 0.0265(8) 0.0187(7) 0.0223(7) -0.0038(6) 0.0084(6) -0.0058(6) O9 0.0198(7) 0.0177(7) 0.0215(7) 0.0055(5) 0.0067(6) 0.0015(6) O10 0.0273(8) 0.0260(8) 0.0232(7) 0.0048(6) 0.0134(6) 0.0040(6) O11 0.0216(7) 0.0167(7) 0.0235(7) -0.0044(5) 0.0083(6) -0.0045(6) O12 0.0232(8) 0.0208(7) 0.0231(7) -0.0041(6) 0.0116(6) -0.0049(6) C1 0.0156(9) 0.0173(10) 0.0171(9) 0.0000(7) 0.0086(8) -0.0008(7) C2 0.0183(10) 0.0188(10) 0.0163(9) -0.0005(7) 0.0074(8) -0.0004(8) C3 0.0182(10) 0.0157(9) 0.0197(9) 0.0013(7) 0.0048(8) -0.0007(8) C4 0.0176(10) 0.0176(10) 0.0199(9) 0.0016(7) 0.0048(8) -0.0004(8) C5 0.0193(10) 0.0162(10) 0.0162(9) 0.0016(7) 0.0040(8) -0.0025(8) C6 0.0181(10) 0.0163(9) 0.0173(9) 0.0007(7) 0.0046(8) 0.0006(8) N1 0.0307(10) 0.0260(10) 0.0190(8) 0.0054(7) 0.0064(8) -0.0044(8) C7 0.0481(15) 0.0269(12) 0.0230(11) -0.0005(9) 0.0155(11) -0.0013(10) C8 0.0607(18) 0.0220(12) 0.0333(12) 0.0034(9) 0.0232(12) 0.0023(11) C9 0.0389(14) 0.0255(12) 0.0328(12) 0.0031(9) 0.0139(11) 0.0020(10) C10 0.0343(15) 0.0398(16) 0.0604(18) 0.0107(13) 0.0141(13) -0.0022(12) C11 0.0322(14) 0.0389(15) 0.0281(12) 0.0038(10) 0.0024(10) -0.0040(11) C12 0.0534(17) 0.0486(18) 0.0336(14) 0.0052(12) 0.0002(12) -0.0191(14) N2 0.0174(9) 0.0304(10) 0.0299(10) 0.0041(8) 0.0068(8) -0.0056(8) C13 0.0331(13) 0.0366(14) 0.0357(13) -0.0031(10) 0.0147(11) -0.0094(11) C14 0.058(2) 0.080(2) 0.0329(14) 0.0087(15) 0.0055(14) -0.0265(18) C15 0.0252(13) 0.0336(14) 0.0682(19) -0.0047(13) 0.0202(13) -0.0004(10) C16 0.0354(15) 0.0237(13) 0.090(2) -0.0063(13) 0.0289(16) -0.0033(11) C17 0.0342(14) 0.062(2) 0.0369(14) 0.0201(13) -0.0054(12) -0.0199(14) C181 0.027(2) 0.045(3) 0.030(2) 0.0057(17) 0.0058(17) -0.0071(18) C182 0.027(4) 0.048(5) 0.063(5) 0.032(4) -0.003(3) -0.012(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.9562(15) . ? Cu1 O7 1.9752(14) . ? Cu1 O8 2.0026(15) 4_565 ? Cu1 O5 2.0057(14) . ? Cu1 O1 2.2207(14) . ? Cu1 O6 2.3210(15) 4_565 ? Cu2 O2 1.9557(14) . ? Cu2 O12 1.9894(14) 3_656 ? Cu2 O9 1.9933(14) . ? Cu2 O11 1.9979(15) . ? Cu2 O4 2.2529(15) . ? Cu2 O10 2.3110(15) 3_756 ? O1 C1 1.237(2) . ? O2 C1 1.262(2) . ? O3 C2 1.264(2) . ? O4 C2 1.234(2) . ? O5 C4 1.277(2) . ? O6 C4 1.227(2) . ? O6 Cu1 2.3210(15) 4_566 ? O7 C3 1.259(2) . ? O8 C3 1.247(2) . ? O8 Cu1 2.0027(15) 4_566 ? O9 C5 1.273(2) . ? O10 C5 1.230(3) . ? O10 Cu2 2.3110(15) 3_756 ? O11 C6 1.250(2) . ? O12 C6 1.251(2) . ? O12 Cu2 1.9894(14) 3_656 ? C1 C2 1.564(3) . ? C3 C4 1.550(3) . ? C5 C5 1.563(4) 3_756 ? C6 C6 1.546(4) 3_656 ? N1 C9 1.498(3) . ? N1 C11 1.499(3) . ? N1 C7 1.505(3) . ? C7 C8 1.510(3) . ? C9 C10 1.506(4) . ? C11 C12 1.494(4) . ? N2 C13 1.494(3) . ? N2 C15 1.495(3) . ? N2 C17 1.500(3) . ? C13 C14 1.512(4) . ? C15 C16 1.512(3) . ? C17 C182 1.348(7) . ? C17 C181 1.418(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O7 176.61(6) . . ? O3 Cu1 O8 92.35(6) . 4_565 ? O7 Cu1 O8 90.94(6) . 4_565 ? O3 Cu1 O5 93.55(6) . . ? O7 Cu1 O5 83.36(6) . . ? O8 Cu1 O5 168.21(6) 4_565 . ? O3 Cu1 O1 80.58(6) . . ? O7 Cu1 O1 98.09(6) . . ? O8 Cu1 O1 99.14(6) 4_565 . ? O5 Cu1 O1 91.89(6) . . ? O3 Cu1 O6 94.62(6) . 4_565 ? O7 Cu1 O6 86.82(6) . 4_565 ? O8 Cu1 O6 78.69(5) 4_565 4_565 ? O5 Cu1 O6 90.67(6) . 4_565 ? O1 Cu1 O6 174.69(5) . 4_565 ? O2 Cu2 O12 177.89(6) . 3_656 ? O2 Cu2 O9 92.12(6) . . ? O12 Cu2 O9 89.84(6) 3_656 . ? O2 Cu2 O11 93.88(6) . . ? O12 Cu2 O11 84.10(6) 3_656 . ? O9 Cu2 O11 172.10(6) . . ? O2 Cu2 O4 80.35(6) . . ? O12 Cu2 O4 100.34(6) 3_656 . ? O9 Cu2 O4 93.12(6) . . ? O11 Cu2 O4 92.94(6) . . ? O2 Cu2 O10 93.70(6) . 3_756 ? O12 Cu2 O10 85.94(6) 3_656 3_756 ? O9 Cu2 O10 77.90(5) . 3_756 ? O11 Cu2 O10 96.58(6) . 3_756 ? O4 Cu2 O10 169.11(5) . 3_756 ? C1 O1 Cu1 107.38(12) . . ? C1 O2 Cu2 116.12(12) . . ? C2 O3 Cu1 116.52(13) . . ? C2 O4 Cu2 107.24(12) . . ? C4 O5 Cu1 111.56(12) . . ? C4 O6 Cu1 105.57(13) . 4_566 ? C3 O7 Cu1 112.40(13) . . ? C3 O8 Cu1 116.07(13) . 4_566 ? C5 O9 Cu2 117.15(12) . . ? C5 O10 Cu2 106.88(12) . 3_756 ? C6 O11 Cu2 110.72(12) . . ? C6 O12 Cu2 111.01(12) . 3_656 ? O1 C1 O2 125.54(19) . . ? O1 C1 C2 117.80(16) . . ? O2 C1 C2 116.66(16) . . ? O4 C2 O3 125.90(19) . . ? O4 C2 C1 118.08(17) . . ? O3 C2 C1 116.01(16) . . ? O8 C3 O7 125.13(19) . . ? O8 C3 C4 118.28(18) . . ? O7 C3 C4 116.59(17) . . ? O6 C4 O5 125.57(19) . . ? O6 C4 C3 119.81(18) . . ? O5 C4 C3 114.62(17) . . ? O10 C5 O9 125.06(18) . . ? O10 C5 C5 119.1(2) . 3_756 ? O9 C5 C5 115.8(2) . 3_756 ? O11 C6 O12 126.57(18) . . ? O11 C6 C6 116.8(2) . 3_656 ? O12 C6 C6 116.7(2) . 3_656 ? C9 N1 C11 112.92(18) . . ? C9 N1 C7 113.90(18) . . ? C11 N1 C7 110.58(19) . . ? N1 C7 C8 114.24(18) . . ? N1 C9 C10 113.3(2) . . ? C12 C11 N1 113.1(2) . . ? C13 N2 C15 114.4(2) . . ? C13 N2 C17 109.8(2) . . ? C15 N2 C17 113.2(2) . . ? N2 C13 C14 113.2(2) . . ? N2 C15 C16 114.6(2) . . ? C182 C17 C181 61.1(4) . . ? C182 C17 N2 117.0(4) . . ? C181 C17 N2 120.4(3) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.815 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.065 # Attachment '- CCDC852904.cif' data_155K _database_code_depnum_ccdc_archive 'CCDC 852904' #TrackingRef '- CCDC852904.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H32 Cu2 N2 O12' _chemical_formula_weight 595.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.71560(10) _cell_length_b 34.0813(4) _cell_length_c 8.63600(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.6320(10) _cell_angle_gamma 90.00 _cell_volume 2444.72(5) _cell_formula_units_Z 4 _cell_measurement_temperature 155(2) _cell_measurement_reflns_used 33567 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description diamondod _exptl_crystal_colour blue _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.802 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.590 _exptl_absorpt_correction_T_max 0.681 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 155(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 'Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28252 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0284 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.53 _reflns_number_total 5535 _reflns_number_gt 4667 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0336P)^2^+1.8141P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5535 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0403 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0821 _refine_ls_wR_factor_gt 0.0789 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.74952(3) 0.203512(7) 0.48285(3) 0.02007(9) Uani 1 1 d . . . Cu2 Cu 0.73860(3) 0.045600(7) 0.49861(3) 0.01947(9) Uani 1 1 d . . . O1 O 0.89530(17) 0.15372(4) 0.61227(17) 0.0232(3) Uani 1 1 d . . . O2 O 0.85006(17) 0.09001(4) 0.62846(16) 0.0233(3) Uani 1 1 d . . . O3 O 0.62165(18) 0.16010(4) 0.36067(17) 0.0263(3) Uani 1 1 d . . . O4 O 0.61226(18) 0.09510(4) 0.34028(18) 0.0269(3) Uani 1 1 d . . . O5 O 0.62391(18) 0.20611(4) 0.64438(17) 0.0249(3) Uani 1 1 d . . . O6 O 0.58961(19) 0.24830(5) 0.82738(19) 0.0318(4) Uani 1 1 d . . . O7 O 0.87528(18) 0.24614(4) 0.61822(18) 0.0264(3) Uani 1 1 d . . . O8 O 0.86017(19) 0.28751(4) 0.81236(18) 0.0272(3) Uani 1 1 d . . . O9 O 0.90657(17) 0.04066(4) 0.38405(17) 0.0240(3) Uani 1 1 d . . . O10 O 1.08905(19) -0.00022(5) 0.34410(18) 0.0292(3) Uani 1 1 d . . . O11 O 0.57042(18) 0.04195(4) 0.61404(17) 0.0244(3) Uani 1 1 d . . . O12 O 0.37925(18) -0.00023(4) 0.62772(17) 0.0254(3) Uani 1 1 d . . . C1 C 0.8187(2) 0.12330(6) 0.5634(2) 0.0189(4) Uani 1 1 d . . . C2 C 0.6699(2) 0.12598(6) 0.4074(2) 0.0199(4) Uani 1 1 d . . . C3 C 0.8123(2) 0.25867(6) 0.7217(2) 0.0213(4) Uani 1 1 d . . . C4 C 0.6620(2) 0.23633(6) 0.7347(2) 0.0220(4) Uani 1 1 d . . . C5 C 1.0005(2) 0.01128(6) 0.4213(2) 0.0205(4) Uani 1 1 d . . . C6 C 0.4851(2) 0.01208(6) 0.5699(2) 0.0211(4) Uani 1 1 d . . . N1 N 0.8997(2) 0.07956(6) 0.0978(2) 0.0311(4) Uani 1 1 d . B . H11 H 0.9143 0.0664 0.1953 0.037 Uiso 1 1 calc R . . C7 C 0.9028(4) 0.12250(7) 0.1365(3) 0.0386(6) Uani 1 1 d . . . H7A H 1.0016 0.1282 0.2266 0.046 Uiso 1 1 calc R . . H7B H 0.8096 0.1286 0.1749 0.046 Uiso 1 1 calc R . . C8 C 0.8983(4) 0.14921(7) -0.0039(3) 0.0448(7) Uani 1 1 d . . . H8A H 0.8921 0.1766 0.0285 0.067 Uiso 1 1 calc R . . H8B H 0.8037 0.1430 -0.0959 0.067 Uiso 1 1 calc R . . H8C H 0.9960 0.1454 -0.0356 0.067 Uiso 1 1 calc R . . C9 C 1.0331(3) 0.06659(7) 0.0348(3) 0.0402(6) Uani 1 1 d . . . H9A H 1.0179 0.0787 -0.0729 0.048 Uiso 1 1 calc R . . H9B H 1.0271 0.0377 0.0200 0.048 Uiso 1 1 calc R . . C10 C 1.1973(3) 0.07727(9) 0.1446(4) 0.0561(8) Uani 1 1 d . . . H10A H 1.2788 0.0694 0.0939 0.084 Uiso 1 1 calc R . . H10B H 1.2169 0.0636 0.2486 0.084 Uiso 1 1 calc R . . H10C H 1.2030 0.1057 0.1630 0.084 Uiso 1 1 calc R . . C11 C 0.7370(3) 0.06797(9) -0.0100(3) 0.0488(8) Uani 1 1 d . . . H11A H 0.7247 0.0770 -0.1218 0.059 Uiso 1 1 calc R A 1 H11B H 0.6537 0.0812 0.0276 0.059 Uiso 1 1 calc R A 1 C121 C 0.7110(9) 0.02448(17) -0.0113(9) 0.0335(19) Uani 0.58(2) 1 d P B 1 H12A H 0.6227 0.0172 -0.1078 0.050 Uiso 0.58(2) 1 calc PR B 1 H12B H 0.6838 0.0168 0.0863 0.050 Uiso 0.58(2) 1 calc PR B 1 H12C H 0.8095 0.0109 -0.0134 0.050 Uiso 0.58(2) 1 calc PR B 1 C122 C 0.657(4) 0.0382(13) -0.003(2) 0.205(15) Uani 0.42(2) 1 d P B 2 H12D H 0.5625 0.0370 -0.0988 0.308 Uiso 0.42(2) 1 calc PR B 2 H12E H 0.6231 0.0394 0.0951 0.308 Uiso 0.42(2) 1 calc PR B 2 H12F H 0.7237 0.0148 0.0014 0.308 Uiso 0.42(2) 1 calc PR B 2 N2 N 0.3407(2) 0.17113(6) 0.6527(2) 0.0307(4) Uani 1 1 d . D . H2 H 0.4349 0.1849 0.6608 0.037 Uiso 1 1 calc R . . C13 C 0.2936(3) 0.18152(8) 0.8002(3) 0.0404(6) Uani 1 1 d . . . H13A H 0.1896 0.1688 0.7928 0.048 Uiso 1 1 calc R . . H13B H 0.2780 0.2103 0.8024 0.048 Uiso 1 1 calc R . . C14 C 0.4170(4) 0.16905(11) 0.9570(4) 0.0678(10) Uani 1 1 d . . . H14A H 0.3781 0.1757 1.0487 0.102 Uiso 1 1 calc R . . H14B H 0.5187 0.1827 0.9685 0.102 Uiso 1 1 calc R . . H14C H 0.4341 0.1406 0.9553 0.102 Uiso 1 1 calc R . . C15 C 0.3790(3) 0.12861(8) 0.6412(4) 0.0464(7) Uani 1 1 d . . . H15A H 0.4738 0.1218 0.7341 0.056 Uiso 1 1 calc R . . H15B H 0.4089 0.1245 0.5408 0.056 Uiso 1 1 calc R . . C16 C 0.2434(3) 0.10091(8) 0.6399(4) 0.0552(8) Uani 1 1 d . . . H16A H 0.2772 0.0738 0.6301 0.083 Uiso 1 1 calc R . . H16B H 0.1491 0.1071 0.5476 0.083 Uiso 1 1 calc R . . H16C H 0.2160 0.1038 0.7410 0.083 Uiso 1 1 calc R . . C17 C 0.2167(4) 0.18635(10) 0.5042(3) 0.0534(8) Uani 1 1 d . . . H17A H 0.1252 0.1678 0.4781 0.064 Uiso 0.73(4) 1 calc PR C 1 H17B H 0.1767 0.2116 0.5339 0.064 Uiso 0.73(4) 1 calc PR C 1 H17C H 0.2149 0.1687 0.4126 0.064 Uiso 0.27(4) 1 d PR C 2 H17D H 0.1103 0.1843 0.5222 0.064 Uiso 0.27(4) 1 d PR C 2 C181 C 0.2568(5) 0.19279(15) 0.3598(5) 0.0420(13) Uani 0.620(7) 1 d P D 1 H18A H 0.1624 0.2028 0.2757 0.063 Uiso 0.620(7) 1 calc PR D 1 H18B H 0.2914 0.1680 0.3235 0.063 Uiso 0.620(7) 1 calc PR D 1 H18C H 0.3443 0.2120 0.3801 0.063 Uiso 0.620(7) 1 calc PR D 1 C182 C 0.2340(8) 0.2234(2) 0.4582(11) 0.053(3) Uani 0.380(7) 1 d P D 2 H18D H 0.1451 0.2299 0.3612 0.080 Uiso 0.380(7) 1 calc PR D 2 H18E H 0.3363 0.2259 0.4340 0.080 Uiso 0.380(7) 1 calc PR D 2 H18F H 0.2333 0.2416 0.5461 0.080 Uiso 0.380(7) 1 calc PR D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02302(15) 0.01566(14) 0.02243(14) -0.00020(9) 0.00824(10) -0.00101(9) Cu2 0.02152(15) 0.01558(14) 0.02224(14) -0.00025(9) 0.00804(10) -0.00204(9) O1 0.0247(8) 0.0185(7) 0.0251(7) -0.0013(6) 0.0054(6) -0.0052(6) O2 0.0256(8) 0.0195(7) 0.0228(7) 0.0023(5) 0.0043(6) -0.0024(6) O3 0.0290(8) 0.0194(7) 0.0260(7) -0.0006(6) 0.0017(6) 0.0024(6) O4 0.0273(8) 0.0205(8) 0.0291(8) -0.0046(6) 0.0029(6) -0.0027(6) O5 0.0249(8) 0.0234(8) 0.0278(7) -0.0038(6) 0.0100(6) -0.0069(6) O6 0.0310(9) 0.0343(9) 0.0352(8) -0.0052(7) 0.0178(7) -0.0011(7) O7 0.0261(8) 0.0252(8) 0.0307(8) -0.0034(6) 0.0131(6) -0.0066(6) O8 0.0322(9) 0.0215(8) 0.0275(7) -0.0053(6) 0.0085(7) -0.0070(6) O9 0.0245(8) 0.0207(7) 0.0265(7) 0.0080(6) 0.0074(6) 0.0019(6) O10 0.0342(9) 0.0304(8) 0.0279(8) 0.0039(6) 0.0169(7) 0.0026(7) O11 0.0263(8) 0.0201(7) 0.0276(7) -0.0057(6) 0.0093(6) -0.0060(6) O12 0.0286(8) 0.0246(8) 0.0262(7) -0.0045(6) 0.0130(6) -0.0062(6) C1 0.0197(10) 0.0202(10) 0.0193(9) -0.0003(7) 0.0099(8) -0.0013(8) C2 0.0203(10) 0.0216(10) 0.0198(9) -0.0013(7) 0.0089(8) -0.0011(8) C3 0.0214(11) 0.0190(10) 0.0223(9) 0.0017(8) 0.0050(8) -0.0002(8) C4 0.0204(10) 0.0209(10) 0.0236(10) 0.0012(8) 0.0050(8) 0.0005(8) C5 0.0225(10) 0.0195(10) 0.0191(9) 0.0023(8) 0.0056(8) -0.0022(8) C6 0.0219(10) 0.0198(10) 0.0211(9) 0.0004(8) 0.0057(8) 0.0005(8) N1 0.0365(11) 0.0328(10) 0.0220(9) 0.0071(7) 0.0057(8) -0.0078(9) C7 0.0556(17) 0.0377(14) 0.0265(11) -0.0003(10) 0.0185(11) -0.0012(12) C8 0.075(2) 0.0273(13) 0.0392(13) 0.0033(10) 0.0277(14) 0.0034(13) C9 0.0512(16) 0.0311(13) 0.0403(14) 0.0042(10) 0.0171(12) 0.0042(12) C10 0.0413(16) 0.0514(18) 0.076(2) 0.0169(15) 0.0191(15) -0.0031(14) C11 0.0428(17) 0.0535(19) 0.0394(15) 0.0113(12) -0.0034(13) -0.0115(13) C121 0.034(3) 0.025(3) 0.032(3) 0.0016(18) -0.003(2) -0.009(2) C122 0.18(2) 0.33(3) 0.046(7) 0.087(13) -0.050(9) -0.20(2) N2 0.0201(9) 0.0353(11) 0.0359(10) 0.0060(8) 0.0073(8) -0.0071(8) C13 0.0399(15) 0.0414(15) 0.0430(14) -0.0029(11) 0.0172(12) -0.0107(12) C14 0.068(2) 0.091(3) 0.0388(16) 0.0101(16) 0.0078(15) -0.0287(19) C15 0.0284(14) 0.0387(15) 0.077(2) -0.0032(13) 0.0232(14) -0.0006(11) C16 0.0408(16) 0.0291(14) 0.104(3) -0.0061(15) 0.0337(17) -0.0045(12) C17 0.0391(15) 0.065(2) 0.0439(15) 0.0211(14) -0.0047(12) -0.0204(14) C181 0.029(2) 0.057(3) 0.040(2) 0.008(2) 0.0094(18) -0.0067(19) C182 0.028(4) 0.052(5) 0.068(5) 0.033(4) -0.003(3) -0.011(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.9573(15) . ? Cu1 O7 1.9754(15) . ? Cu1 O8 2.0165(15) 4_565 ? Cu1 O5 2.0230(14) . ? Cu1 O1 2.2093(14) . ? Cu1 O6 2.3040(16) 4_565 ? Cu2 O2 1.9571(14) . ? Cu2 O12 1.9888(14) 3_656 ? Cu2 O9 2.0103(15) . ? Cu2 O11 2.0140(15) . ? Cu2 O4 2.2394(15) . ? Cu2 O10 2.2930(16) 3_756 ? O1 C1 1.236(2) . ? O2 C1 1.258(2) . ? O3 C2 1.260(2) . ? O4 C2 1.232(2) . ? O5 C4 1.274(2) . ? O6 C4 1.231(3) . ? O6 Cu1 2.3040(16) 4_566 ? O7 C3 1.259(2) . ? O8 C3 1.247(2) . ? O8 Cu1 2.0165(15) 4_566 ? O9 C5 1.271(2) . ? O10 C5 1.229(3) . ? O10 Cu2 2.2930(16) 3_756 ? O11 C6 1.250(2) . ? O12 C6 1.249(3) . ? O12 Cu2 1.9888(14) 3_656 ? C1 C2 1.566(3) . ? C3 C4 1.549(3) . ? C5 C5 1.566(4) 3_756 ? C6 C6 1.549(4) 3_656 ? N1 C9 1.494(3) . ? N1 C11 1.496(3) . ? N1 C7 1.498(3) . ? C7 C8 1.508(3) . ? C9 C10 1.504(4) . ? C11 C122 1.241(18) . ? C11 C121 1.497(7) . ? N2 C15 1.496(3) . ? N2 C13 1.497(3) . ? N2 C17 1.499(3) . ? C13 C14 1.514(4) . ? C15 C16 1.510(4) . ? C17 C182 1.346(8) . ? C17 C181 1.412(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O7 176.43(6) . . ? O3 Cu1 O8 92.31(6) . 4_565 ? O7 Cu1 O8 91.11(6) . 4_565 ? O3 Cu1 O5 93.82(6) . . ? O7 Cu1 O5 83.00(6) . . ? O8 Cu1 O5 168.21(6) 4_565 . ? O3 Cu1 O1 80.82(6) . . ? O7 Cu1 O1 97.61(6) . . ? O8 Cu1 O1 99.05(6) 4_565 . ? O5 Cu1 O1 91.88(6) . . ? O3 Cu1 O6 94.44(6) . 4_565 ? O7 Cu1 O6 87.26(6) . 4_565 ? O8 Cu1 O6 78.73(6) 4_565 4_565 ? O5 Cu1 O6 90.75(6) . 4_565 ? O1 Cu1 O6 174.72(5) . 4_565 ? O2 Cu2 O12 177.92(6) . 3_656 ? O2 Cu2 O9 92.18(6) . . ? O12 Cu2 O9 89.82(6) 3_656 . ? O2 Cu2 O11 94.18(6) . . ? O12 Cu2 O11 83.78(6) 3_656 . ? O9 Cu2 O11 171.67(6) . . ? O2 Cu2 O4 80.59(6) . . ? O12 Cu2 O4 99.89(6) 3_656 . ? O9 Cu2 O4 93.35(6) . . ? O11 Cu2 O4 93.00(6) . . ? O2 Cu2 O10 93.30(6) . 3_756 ? O12 Cu2 O10 86.54(6) 3_656 3_756 ? O9 Cu2 O10 77.96(5) . 3_756 ? O11 Cu2 O10 96.28(6) . 3_756 ? O4 Cu2 O10 169.25(6) . 3_756 ? C1 O1 Cu1 107.52(13) . . ? C1 O2 Cu2 115.88(12) . . ? C2 O3 Cu1 116.28(13) . . ? C2 O4 Cu2 107.40(13) . . ? C4 O5 Cu1 111.37(13) . . ? C4 O6 Cu1 106.05(14) . 4_566 ? C3 O7 Cu1 112.76(13) . . ? C3 O8 Cu1 115.85(13) . 4_566 ? C5 O9 Cu2 116.82(12) . . ? C5 O10 Cu2 107.41(12) . 3_756 ? C6 O11 Cu2 110.78(13) . . ? C6 O12 Cu2 111.25(13) . 3_656 ? O1 C1 O2 125.48(19) . . ? O1 C1 C2 117.84(16) . . ? O2 C1 C2 116.68(16) . . ? O4 C2 O3 125.93(19) . . ? O4 C2 C1 118.01(17) . . ? O3 C2 C1 116.05(16) . . ? O8 C3 O7 125.38(19) . . ? O8 C3 C4 118.05(18) . . ? O7 C3 C4 116.57(17) . . ? O6 C4 O5 125.3(2) . . ? O6 C4 C3 119.85(18) . . ? O5 C4 C3 114.88(18) . . ? O10 C5 O9 125.18(18) . . ? O10 C5 C5 119.2(2) . 3_756 ? O9 C5 C5 115.7(2) . 3_756 ? O12 C6 O11 126.53(18) . . ? O12 C6 C6 117.0(2) . 3_656 ? O11 C6 C6 116.4(2) . 3_656 ? C9 N1 C11 113.1(2) . . ? C9 N1 C7 113.98(19) . . ? C11 N1 C7 110.2(2) . . ? N1 C7 C8 114.46(19) . . ? N1 C9 C10 113.3(2) . . ? C122 C11 N1 128.6(13) . . ? C122 C11 C121 27(3) . . ? N1 C11 C121 112.2(3) . . ? C15 N2 C13 114.2(2) . . ? C15 N2 C17 113.3(2) . . ? C13 N2 C17 109.7(2) . . ? N2 C13 C14 113.2(2) . . ? N2 C15 C16 114.5(2) . . ? C182 C17 C181 60.9(4) . . ? C182 C17 N2 117.5(4) . . ? C181 C17 N2 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.676 _refine_diff_density_min -0.379 _refine_diff_density_rms 0.063 # Attachment '- CCDC852905.cif' data_180K _database_code_depnum_ccdc_archive 'CCDC 852905' #TrackingRef '- CCDC852905.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H32 Cu2 N2 O12' _chemical_formula_weight 595.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.74070(10) _cell_length_b 33.9886(4) _cell_length_c 8.67710(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.7250(10) _cell_angle_gamma 90.00 _cell_volume 2455.46(5) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 28965 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 27.52 _exptl_crystal_description diamondiod _exptl_crystal_colour blue _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4796 _exptl_absorpt_correction_T_max 0.6936 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28663 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.41 _diffrn_reflns_theta_max 27.52 _reflns_number_total 5569 _reflns_number_gt 4523 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0401P)^2^+2.3414P] 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 refxyz _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5569 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0885 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.75056(3) 0.203578(7) 0.48505(3) 0.02339(9) Uani 1 1 d . . . Cu2 Cu 0.73979(3) 0.045729(7) 0.49924(3) 0.02276(9) Uani 1 1 d . . . O1 O 0.89475(19) 0.15421(4) 0.61392(18) 0.0284(3) Uani 1 1 d . . . O2 O 0.85275(19) 0.09016(4) 0.62874(18) 0.0285(3) Uani 1 1 d . . . O3 O 0.6220(2) 0.15999(5) 0.36281(19) 0.0320(4) Uani 1 1 d . . . O4 O 0.61334(19) 0.09481(5) 0.34448(19) 0.0325(4) Uani 1 1 d . . . O5 O 0.62451(19) 0.20661(5) 0.64767(18) 0.0297(3) Uani 1 1 d . . . O6 O 0.5938(2) 0.24885(5) 0.8313(2) 0.0384(4) Uani 1 1 d . . . O7 O 0.87709(19) 0.24604(5) 0.62152(19) 0.0314(4) Uani 1 1 d . . . O8 O 0.8631(2) 0.28759(5) 0.81501(19) 0.0327(4) Uani 1 1 d . . . O9 O 0.90827(19) 0.04046(4) 0.38243(19) 0.0307(4) Uani 1 1 d . . . O10 O 1.0904(2) -0.00100(5) 0.3463(2) 0.0362(4) Uani 1 1 d . . . O11 O 0.57127(19) 0.04165(4) 0.61610(19) 0.0297(3) Uani 1 1 d . . . O12 O 0.3800(2) -0.00071(5) 0.62764(19) 0.0307(4) Uani 1 1 d . . . C1 C 0.8196(3) 0.12345(6) 0.5647(2) 0.0229(4) Uani 1 1 d . . . C2 C 0.6713(3) 0.12595(6) 0.4098(3) 0.0243(4) Uani 1 1 d . . . C3 C 0.8146(3) 0.25882(6) 0.7246(2) 0.0249(4) Uani 1 1 d . . . C4 C 0.6644(3) 0.23659(6) 0.7379(3) 0.0264(5) Uani 1 1 d . . . C5 C 1.0008(3) 0.01101(6) 0.4217(2) 0.0245(4) Uani 1 1 d . . . C6 C 0.4857(3) 0.01186(6) 0.5706(2) 0.0250(4) Uani 1 1 d . . . N1 N 0.9034(3) 0.07874(6) 0.0971(2) 0.0392(5) Uani 1 1 d . A . H1 H 0.9175 0.0652 0.1937 0.047 Uiso 1 1 calc R . . C7 C 0.9043(4) 0.12162(8) 0.1370(3) 0.0469(7) Uani 1 1 d . . . H7A H 1.0022 0.1274 0.2276 0.056 Uiso 1 1 calc R . . H7B H 0.8105 0.1273 0.1747 0.056 Uiso 1 1 calc R . . C8 C 0.8994(4) 0.14884(8) -0.0012(3) 0.0537(8) Uani 1 1 d . . . H8A H 0.8933 0.1761 0.0328 0.081 Uiso 1 1 calc R . . H8B H 0.8049 0.1428 -0.0932 0.081 Uiso 1 1 calc R . . H8C H 0.9969 0.1453 -0.0331 0.081 Uiso 1 1 calc R . . C9 C 1.0378(4) 0.06654(9) 0.0357(4) 0.0506(7) Uani 1 1 d . . . H9A H 1.0240 0.0793 -0.0703 0.061 Uiso 1 1 calc R . . H9B H 1.0324 0.0377 0.0182 0.061 Uiso 1 1 calc R . . C10 C 1.2005(4) 0.07697(11) 0.1482(5) 0.0712(10) Uani 1 1 d . . . H10A H 1.2833 0.0693 0.0992 0.107 Uiso 1 1 calc R . . H10B H 1.2183 0.0630 0.2510 0.107 Uiso 1 1 calc R . . H10C H 1.2061 0.1054 0.1680 0.107 Uiso 1 1 calc R . . C11 C 0.7416(4) 0.06700(12) -0.0129(4) 0.0753(13) Uani 1 1 d . . . H11 H 0.730(3) 0.0771(8) -0.110(4) 0.042(8) Uiso 1 1 d . . . C121 C 0.6291(14) 0.0515(6) 0.0123(10) 0.074(6) Uani 0.356(12) 1 d P A 1 H12A H 0.5592 0.0402 -0.0885 0.111 Uiso 0.356(12) 1 calc PR A 1 H12B H 0.5689 0.0710 0.0537 0.111 Uiso 0.356(12) 1 calc PR A 1 H12C H 0.6668 0.0306 0.0926 0.111 Uiso 0.356(12) 1 calc PR A 1 C122 C 0.7060(8) 0.02511(18) -0.0102(6) 0.0515(19) Uani 0.644(12) 1 d P A 2 H12D H 0.6018 0.0196 -0.0899 0.077 Uiso 0.644(12) 1 calc PR A 2 H12E H 0.7026 0.0177 0.0979 0.077 Uiso 0.644(12) 1 calc PR A 2 H12F H 0.7898 0.0099 -0.0369 0.077 Uiso 0.644(12) 1 calc PR A 2 N2 N 0.3416(2) 0.17145(6) 0.6564(2) 0.0360(5) Uani 1 1 d . B 2 H2 H 0.4354 0.1853 0.6645 0.043 Uiso 1 1 calc R B 2 C13 C 0.2941(4) 0.18194(9) 0.8026(3) 0.0488(7) Uani 1 1 d . B 2 H13A H 0.1904 0.1691 0.7951 0.059 Uiso 1 1 calc R B 2 H13B H 0.2780 0.2108 0.8041 0.059 Uiso 1 1 calc R B 2 C14 C 0.4176(5) 0.16969(13) 0.9596(4) 0.0796(12) Uani 1 1 d . B 2 H14A H 0.3784 0.1764 1.0508 0.119 Uiso 1 1 calc R B 2 H14B H 0.5189 0.1835 0.9711 0.119 Uiso 1 1 calc R B 2 H14C H 0.4354 0.1412 0.9584 0.119 Uiso 1 1 calc R B 2 C15 C 0.3810(3) 0.12891(8) 0.6462(4) 0.0523(8) Uani 1 1 d . B 2 H15A H 0.4749 0.1223 0.7400 0.063 Uiso 1 1 calc R B 2 H15B H 0.4126 0.1248 0.5470 0.063 Uiso 1 1 calc R B 2 C16 C 0.2464(4) 0.10100(9) 0.6433(5) 0.0631(9) Uani 1 1 d . B 2 H16A H 0.2809 0.0739 0.6335 0.095 Uiso 1 1 calc R B 2 H16B H 0.1526 0.1072 0.5507 0.095 Uiso 1 1 calc R B 2 H16C H 0.2181 0.1037 0.7437 0.095 Uiso 1 1 calc R B 2 C17 C 0.2175(4) 0.18687(11) 0.5097(4) 0.0613(10) Uani 1 1 d . B 2 H17A H 0.2158 0.1696 0.4175 0.074 Uiso 0.602(8) 1 calc PR C 1 H17B H 0.1114 0.1845 0.5279 0.074 Uiso 0.602(8) 1 calc PR C 1 H17C H 0.2158 0.1696 0.4175 0.074 Uiso 0.398(8) 1 calc PR C 2 H17D H 0.1114 0.1845 0.5279 0.074 Uiso 0.398(8) 1 calc PR C 2 C181 C 0.2594(5) 0.19255(17) 0.3627(6) 0.0493(17) Uani 0.602(8) 1 d P C 1 H18A H 0.1834 0.2124 0.3016 0.074 Uiso 0.602(8) 1 calc PR C 1 H18B H 0.3671 0.1985 0.3567 0.074 Uiso 0.602(8) 1 calc PR C 1 H18C H 0.2607 0.1929 0.4761 0.074 Uiso 0.602(8) 1 calc PR C 1 C182 C 0.2344(9) 0.2243(3) 0.4659(12) 0.074(4) Uani 0.398(8) 1 d P B 2 H18D H 0.1458 0.2309 0.3690 0.110 Uiso 0.398(8) 1 calc PR C 2 H18E H 0.3368 0.2271 0.4426 0.110 Uiso 0.398(8) 1 calc PR C 2 H18F H 0.2328 0.2421 0.5542 0.110 Uiso 0.398(8) 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.02633(16) 0.01864(15) 0.02597(15) 0.00011(9) 0.00910(11) -0.00093(10) Cu2 0.02495(16) 0.01820(15) 0.02597(15) -0.00015(9) 0.00901(11) -0.00219(10) O1 0.0311(8) 0.0224(8) 0.0299(8) -0.0017(6) 0.0066(7) -0.0075(7) O2 0.0323(9) 0.0231(8) 0.0275(7) 0.0024(6) 0.0052(7) -0.0028(6) O3 0.0348(9) 0.0239(8) 0.0318(8) -0.0009(6) 0.0022(7) 0.0020(7) O4 0.0324(9) 0.0254(8) 0.0361(9) -0.0066(7) 0.0048(7) -0.0044(7) O5 0.0283(8) 0.0297(9) 0.0318(8) -0.0040(6) 0.0103(7) -0.0093(7) O6 0.0380(10) 0.0431(10) 0.0398(9) -0.0042(8) 0.0204(8) 0.0021(8) O7 0.0301(9) 0.0303(9) 0.0364(8) -0.0047(7) 0.0141(7) -0.0082(7) O8 0.0370(9) 0.0258(8) 0.0337(8) -0.0070(7) 0.0084(7) -0.0094(7) O9 0.0307(9) 0.0260(8) 0.0332(8) 0.0108(6) 0.0063(7) 0.0011(7) O10 0.0429(10) 0.0379(10) 0.0345(9) 0.0021(7) 0.0219(8) 0.0000(8) O11 0.0315(9) 0.0244(8) 0.0329(8) -0.0066(6) 0.0091(7) -0.0080(7) O12 0.0354(9) 0.0301(9) 0.0302(8) -0.0054(6) 0.0152(7) -0.0087(7) C1 0.0250(11) 0.0230(11) 0.0231(10) 0.0005(8) 0.0110(9) -0.0016(8) C2 0.0252(11) 0.0245(11) 0.0257(10) -0.0026(8) 0.0113(9) -0.0010(9) C3 0.0250(11) 0.0213(11) 0.0263(10) 0.0019(8) 0.0047(9) -0.0004(9) C4 0.0234(11) 0.0273(11) 0.0276(10) 0.0012(9) 0.0065(9) 0.0007(9) C5 0.0257(11) 0.0226(11) 0.0239(10) 0.0023(8) 0.0055(9) -0.0028(9) C6 0.0260(11) 0.0231(11) 0.0241(10) 0.0007(8) 0.0052(9) -0.0015(9) N1 0.0450(13) 0.0424(12) 0.0256(9) 0.0106(8) 0.0038(9) -0.0117(10) C7 0.067(2) 0.0469(16) 0.0315(13) -0.0010(11) 0.0220(13) -0.0030(14) C8 0.089(2) 0.0338(15) 0.0464(15) 0.0055(12) 0.0326(16) 0.0043(15) C9 0.066(2) 0.0399(16) 0.0496(16) 0.0056(12) 0.0227(15) 0.0065(14) C10 0.052(2) 0.070(2) 0.094(3) 0.025(2) 0.0249(19) -0.0024(17) C11 0.063(2) 0.081(3) 0.055(2) 0.0334(18) -0.0234(18) -0.0346(19) C121 0.048(6) 0.138(15) 0.027(4) 0.016(5) 0.000(4) -0.028(8) C122 0.052(3) 0.052(3) 0.038(2) 0.006(2) -0.007(2) -0.019(3) N2 0.0227(10) 0.0420(12) 0.0415(11) 0.0071(9) 0.0073(9) -0.0091(9) C13 0.0473(17) 0.0518(18) 0.0501(16) -0.0037(13) 0.0187(13) -0.0141(14) C14 0.081(3) 0.106(3) 0.0440(18) 0.0103(19) 0.0081(17) -0.031(2) C15 0.0315(15) 0.0469(17) 0.083(2) 0.0000(15) 0.0247(15) -0.0005(12) C16 0.0453(18) 0.0363(16) 0.115(3) -0.0045(17) 0.0362(19) -0.0040(13) C17 0.0412(16) 0.085(3) 0.0487(17) 0.0248(16) 0.0001(13) -0.0231(16) C181 0.030(2) 0.075(4) 0.042(3) 0.017(2) 0.0094(19) -0.011(2) C182 0.042(5) 0.058(6) 0.093(7) 0.039(5) -0.021(5) -0.009(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.9639(16) . ? Cu1 O7 1.9775(16) . ? Cu1 O8 2.0293(17) 4_565 ? Cu1 O5 2.0401(16) . ? Cu1 O1 2.1899(16) . ? Cu1 O6 2.2712(18) 4_565 ? Cu2 O2 1.9601(15) . ? Cu2 O12 1.9869(15) 3_656 ? Cu2 O11 2.0314(16) . ? Cu2 O9 2.0340(17) . ? Cu2 O4 2.2144(16) . ? Cu2 O10 2.2582(18) 3_756 ? O1 C1 1.240(2) . ? O2 C1 1.255(2) . ? O3 C2 1.258(3) . ? O4 C2 1.234(3) . ? O5 C4 1.267(3) . ? O6 C4 1.231(3) . ? O6 Cu1 2.2712(18) 4_566 ? O7 C3 1.259(3) . ? O8 C3 1.244(3) . ? O8 Cu1 2.0293(17) 4_566 ? O9 C5 1.267(3) . ? O10 C5 1.232(3) . ? O10 Cu2 2.2582(18) 3_756 ? O11 C6 1.249(3) . ? O12 C6 1.249(3) . ? O12 Cu2 1.9869(15) 3_656 ? C1 C2 1.560(3) . ? C3 C4 1.549(3) . ? C5 C5 1.556(4) 3_756 ? C6 C6 1.549(4) 3_656 ? N1 C9 1.489(4) . ? N1 C7 1.497(3) . ? N1 C11 1.500(4) . ? N1 H1 0.9300 . ? C7 C8 1.504(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.502(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C121 1.193(9) . ? C11 C122 1.459(6) . ? C11 H11 0.89(3) . ? C121 H12A 0.9800 . ? C121 H12B 0.9800 . ? C121 H12C 0.9800 . ? C122 H12D 0.9800 . ? C122 H12E 0.9800 . ? C122 H12F 0.9800 . ? N2 C13 1.492(3) . ? N2 C15 1.495(3) . ? N2 C17 1.493(3) . ? N2 H2 0.9300 . ? C13 C14 1.516(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.506(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C182 1.349(9) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 H17C 0.9900 . ? C17 H17D 0.9900 . ? C181 H18A 0.9800 . ? C181 H18B 0.9800 . ? C181 H18C 0.9800 . ? C182 H18D 0.9800 . ? C182 H18E 0.9800 . ? C182 H18F 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O7 176.08(7) . . ? O3 Cu1 O8 92.47(7) . 4_565 ? O7 Cu1 O8 91.19(7) . 4_565 ? O3 Cu1 O5 94.08(7) . . ? O7 Cu1 O5 82.55(6) . . ? O8 Cu1 O5 168.16(7) 4_565 . ? O3 Cu1 O1 80.99(6) . . ? O7 Cu1 O1 97.09(6) . . ? O8 Cu1 O1 98.84(6) 4_565 . ? O5 Cu1 O1 91.93(6) . . ? O3 Cu1 O6 94.37(7) . 4_565 ? O7 Cu1 O6 87.68(7) . 4_565 ? O8 Cu1 O6 78.85(6) 4_565 4_565 ? O5 Cu1 O6 90.81(6) . 4_565 ? O1 Cu1 O6 174.77(6) . 4_565 ? O2 Cu2 O12 178.04(6) . 3_656 ? O2 Cu2 O11 94.68(6) . . ? O12 Cu2 O11 83.36(6) 3_656 . ? O2 Cu2 O9 92.22(7) . . ? O12 Cu2 O9 89.73(6) 3_656 . ? O11 Cu2 O9 171.03(7) . . ? O2 Cu2 O4 80.72(6) . . ? O12 Cu2 O4 99.36(6) 3_656 . ? O11 Cu2 O4 92.88(6) . . ? O9 Cu2 O4 93.87(6) . . ? O2 Cu2 O10 93.04(6) . 3_756 ? O12 Cu2 O10 87.17(7) 3_656 3_756 ? O11 Cu2 O10 95.94(6) . 3_756 ? O9 Cu2 O10 77.96(6) . 3_756 ? O4 Cu2 O10 169.59(6) . 3_756 ? C1 O1 Cu1 107.94(13) . . ? C1 O2 Cu2 115.63(13) . . ? C2 O3 Cu1 115.83(14) . . ? C2 O4 Cu2 107.97(14) . . ? C4 O5 Cu1 111.26(13) . . ? C4 O6 Cu1 107.11(15) . 4_566 ? C3 O7 Cu1 113.12(14) . . ? C3 O8 Cu1 115.29(14) . 4_566 ? C5 O9 Cu2 115.84(13) . . ? C5 O10 Cu2 108.50(14) . 3_756 ? C6 O11 Cu2 110.65(14) . . ? C6 O12 Cu2 111.86(13) . 3_656 ? O1 C1 O2 125.5(2) . . ? O1 C1 C2 117.71(17) . . ? O2 C1 C2 116.75(17) . . ? O4 C2 O3 126.0(2) . . ? O4 C2 C1 117.77(18) . . ? O3 C2 C1 116.23(17) . . ? O8 C3 O7 125.5(2) . . ? O8 C3 C4 118.0(2) . . ? O7 C3 C4 116.45(19) . . ? O6 C4 O5 125.4(2) . . ? O6 C4 C3 119.3(2) . . ? O5 C4 C3 115.25(19) . . ? O10 C5 O9 125.19(19) . . ? O10 C5 C5 118.7(2) . 3_756 ? O9 C5 C5 116.1(2) . 3_756 ? O12 C6 O11 126.6(2) . . ? O12 C6 C6 116.9(2) . 3_656 ? O11 C6 C6 116.5(2) . 3_656 ? C9 N1 C7 113.9(2) . . ? C9 N1 C11 113.1(3) . . ? C7 N1 C11 110.1(3) . . ? C9 N1 H1 106.4 . . ? C7 N1 H1 106.4 . . ? C11 N1 H1 106.4 . . ? N1 C7 C8 114.7(2) . . ? N1 C7 H7A 108.6 . . ? C8 C7 H7A 108.6 . . ? N1 C7 H7B 108.6 . . ? C8 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 C10 113.3(3) . . ? N1 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C121 C11 C122 51.3(8) . . ? C121 C11 N1 132.1(5) . . ? C122 C11 N1 114.4(3) . . ? C121 C11 H11 119.2(19) . . ? C122 C11 H11 115.6(19) . . ? N1 C11 H11 108.1(19) . . ? C11 C121 H12A 109.5 . . ? C11 C121 H12B 109.5 . . ? H12A C121 H12B 109.5 . . ? C11 C121 H12C 109.5 . . ? H12A C121 H12C 109.5 . . ? H12B C121 H12C 109.5 . . ? C11 C122 H12D 109.5 . . ? C11 C122 H12E 109.5 . . ? H12D C122 H12E 109.5 . . ? C11 C122 H12F 109.5 . . ? H12D C122 H12F 109.5 . . ? H12E C122 H12F 109.5 . . ? C13 N2 C15 114.2(2) . . ? C13 N2 C17 108.8(2) . . ? C15 N2 C17 114.2(2) . . ? C13 N2 H2 106.3 . . ? C15 N2 H2 106.3 . . ? C17 N2 H2 106.3 . . ? N2 C13 C14 113.1(3) . . ? N2 C13 H13A 109.0 . . ? C14 C13 H13A 109.0 . . ? N2 C13 H13B 109.0 . . ? C14 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 114.6(2) . . ? N2 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? N2 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C182 C17 N2 117.3(4) . . ? C182 C17 H17A 108.0 . . ? N2 C17 H17A 108.0 . . ? C182 C17 H17B 108.0 . . ? N2 C17 H17B 108.0 . . ? H17A C17 H17B 107.2 . . ? C182 C17 H17C 108.0 . . ? N2 C17 H17C 108.0 . . ? H17A C17 H17C 0.0 . . ? H17B C17 H17C 107.2 . . ? C182 C17 H17D 108.0 . . ? N2 C17 H17D 108.0 . . ? H17A C17 H17D 107.2 . . ? H17B C17 H17D 0.0 . . ? H17C C17 H17D 107.2 . . ? H18A C181 H18B 109.5 . . ? H18A C181 H18C 109.5 . . ? H18B C181 H18C 109.5 . . ? C17 C182 H18D 109.5 . . ? C17 C182 H18E 109.5 . . ? H18D C182 H18E 109.5 . . ? C17 C182 H18F 109.5 . . ? H18D C182 H18F 109.5 . . ? H18E C182 H18F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.540 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.064 # Attachment '- CCDC852906.cif' data_293K _database_code_depnum_ccdc_archive 'CCDC 852906' #TrackingRef '- CCDC852906.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H32 Cu2 N2 O12' _chemical_formula_weight 595.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/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 8.82940(10) _cell_length_b 33.7719(4) _cell_length_c 8.80520(10) _cell_angle_alpha 90.00 _cell_angle_beta 107.9010(10) _cell_angle_gamma 90.00 _cell_volume 2498.48(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 26836 _cell_measurement_theta_min 3.395 _cell_measurement_theta_max 27.485 _exptl_crystal_description diamondiod _exptl_crystal_colour blue _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 1.764 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.582 _exptl_absorpt_correction_T_max 0.683 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30048 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0320 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.42 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5699 _reflns_number_gt 3688 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0432P)^2^+0.3834P] 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 SHELXL _refine_ls_extinction_coef 0.0036(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5699 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0593 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0893 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.74696(3) 0.204056(8) 0.49762(3) 0.03816(10) Uani 1 1 d . . . Cu2 Cu 0.74245(3) 0.045688(8) 0.50213(3) 0.03740(10) Uani 1 1 d . . . O1 O 0.88655(19) 0.15532(4) 0.62326(17) 0.0468(4) Uani 1 1 d . . . O2 O 0.85720(18) 0.09044(4) 0.63137(17) 0.0462(4) Uani 1 1 d . . . O3 O 0.6182(2) 0.15975(5) 0.37507(18) 0.0521(4) Uani 1 1 d . . . O4 O 0.61566(19) 0.09430(5) 0.35658(19) 0.0531(4) Uani 1 1 d . . . O5 O 0.61971(18) 0.20803(5) 0.66086(18) 0.0486(4) Uani 1 1 d . . . O6 O 0.5986(2) 0.24970(5) 0.8471(2) 0.0588(5) Uani 1 1 d . . . O7 O 0.87458(19) 0.24621(5) 0.63821(19) 0.0497(4) Uani 1 1 d . . . O8 O 0.86357(19) 0.28758(5) 0.82979(19) 0.0521(4) Uani 1 1 d . . . O9 O 0.91069(19) 0.04012(5) 0.38113(18) 0.0496(4) Uani 1 1 d . . . O10 O 1.0920(2) -0.00176(5) 0.35085(19) 0.0578(4) Uani 1 1 d . . . O11 O 0.57550(19) 0.04031(5) 0.62238(19) 0.0494(4) Uani 1 1 d . . . O12 O 0.38242(19) -0.00149(5) 0.62604(18) 0.0489(4) Uani 1 1 d . . . C1 C 0.8187(3) 0.12392(6) 0.5723(2) 0.0365(5) Uani 1 1 d . . . C2 C 0.6699(3) 0.12601(7) 0.4203(3) 0.0387(5) Uani 1 1 d . . . C3 C 0.8145(3) 0.25919(6) 0.7389(3) 0.0400(5) Uani 1 1 d . . . C4 C 0.6647(2) 0.23731(7) 0.7520(3) 0.0396(5) Uani 1 1 d . . . C5 C 1.0023(3) 0.01086(6) 0.4224(2) 0.0391(5) Uani 1 1 d . . . C6 C 0.4880(3) 0.01140(6) 0.5719(2) 0.0390(5) Uani 1 1 d . . . N1 N 0.9096(3) 0.07731(6) 0.0980(2) 0.0600(6) Uani 1 1 d . . . H1 H 0.9265 0.0638 0.1912 0.072 Uiso 1 1 calc R A 1 C7 C 0.9017(4) 0.11985(8) 0.1417(3) 0.0752(9) Uani 1 1 d . B . H7A H 0.9938 0.1259 0.2323 0.090 Uiso 1 1 calc R . . H7B H 0.8078 0.1237 0.1752 0.090 Uiso 1 1 calc R . . C8 C 0.8961(5) 0.14864(8) 0.0099(3) 0.0941(11) Uani 1 1 d . . . H8A H 0.8901 0.1752 0.0469 0.141 Uiso 1 1 calc R B . H8B H 0.8042 0.1433 -0.0799 0.141 Uiso 1 1 calc R . . H8C H 0.9905 0.1458 -0.0215 0.141 Uiso 1 1 calc R . . C9 C 1.0495(4) 0.06745(9) 0.0424(4) 0.0870(10) Uani 1 1 d . B . H9A H 1.0466 0.0394 0.0181 0.104 Uiso 1 1 calc R . . H9B H 1.0395 0.0818 -0.0556 0.104 Uiso 1 1 calc R . . C10 C 1.2055(4) 0.07690(13) 0.1591(5) 0.1339(17) Uani 1 1 d . . . H10A H 1.2889 0.0699 0.1153 0.201 Uiso 1 1 calc R B . H10B H 1.2181 0.0622 0.2556 0.201 Uiso 1 1 calc R . . H10C H 1.2109 0.1047 0.1821 0.201 Uiso 1 1 calc R . . C111 C 0.736(2) 0.0690(6) 0.003(2) 0.068(3) Uani 0.45(3) 1 d P B 1 H11A H 0.6663 0.0831 0.0513 0.082 Uiso 0.45(3) 1 calc PR B 1 H11B H 0.7145 0.0785 -0.1053 0.082 Uiso 0.45(3) 1 calc PR B 1 C112 C 0.7772(19) 0.0591(5) -0.0367(16) 0.064(3) Uani 0.55(3) 1 d P B 2 H11C H 0.7489 0.0770 -0.1273 0.077 Uiso 0.55(3) 1 calc PR B 2 H11D H 0.8141 0.0345 -0.0700 0.077 Uiso 0.55(3) 1 calc PR B 2 C121 C 0.702(2) 0.0262(5) 0.0007(12) 0.101(5) Uani 0.51(2) 1 d P B 1 H12A H 0.6157 0.0199 -0.0936 0.151 Uiso 0.51(2) 1 calc PR B 1 H12B H 0.6719 0.0193 0.0935 0.151 Uiso 0.51(2) 1 calc PR B 1 H12C H 0.7947 0.0115 0.0005 0.151 Uiso 0.51(2) 1 calc PR B 1 C122 C 0.6351(13) 0.0513(6) 0.0147(9) 0.080(4) Uani 0.49(2) 1 d P B 2 H12D H 0.5438 0.0478 -0.0775 0.120 Uiso 0.49(2) 1 calc PR B 2 H12E H 0.6175 0.0733 0.0762 0.120 Uiso 0.49(2) 1 calc PR B 2 H12F H 0.6521 0.0277 0.0788 0.120 Uiso 0.49(2) 1 calc PR B 2 N2 N 0.3397(2) 0.17202(6) 0.6722(2) 0.0595(6) Uani 1 1 d . D . H2 H 0.4299 0.1862 0.6822 0.071 Uiso 1 1 calc R . . C13 C 0.2910(4) 0.18146(10) 0.8154(4) 0.0838(9) Uani 1 1 d . . . H13A H 0.1928 0.1675 0.8076 0.101 Uiso 1 1 calc R . . H13B H 0.2694 0.2096 0.8157 0.101 Uiso 1 1 calc R . . C14 C 0.4129(5) 0.17070(13) 0.9709(4) 0.1360(17) Uani 1 1 d . . . H14A H 0.3732 0.1774 1.0576 0.204 Uiso 1 1 calc R . . H14B H 0.5095 0.1851 0.9816 0.204 Uiso 1 1 calc R . . H14C H 0.4339 0.1428 0.9727 0.204 Uiso 1 1 calc R . . C15 C 0.3821(3) 0.12949(9) 0.6590(4) 0.0789(9) Uani 1 1 d . . . H15A H 0.4139 0.1263 0.5635 0.095 Uiso 1 1 calc R . . H15B H 0.4732 0.1229 0.7498 0.095 Uiso 1 1 calc R . . C16 C 0.2510(4) 0.10083(9) 0.6521(5) 0.1036(12) Uani 1 1 d . . . H16A H 0.2868 0.0744 0.6425 0.155 Uiso 1 1 calc R . . H16B H 0.1606 0.1068 0.5615 0.155 Uiso 1 1 calc R . . H16C H 0.2213 0.1030 0.7479 0.155 Uiso 1 1 calc R . . C17 C 0.2175(4) 0.18760(12) 0.5267(4) 0.0879(11) Uani 1 1 d . . . H17A H 0.1270 0.1698 0.5021 0.105 Uiso 0.70(4) 1 calc PR C 1 H17B H 0.1815 0.2129 0.5544 0.105 Uiso 0.70(4) 1 calc PR C 1 H17C H 0.2157 0.1700 0.4352 0.105 Uiso 0.30(4) 1 d PR C 2 H17D H 0.1111 0.1856 0.5448 0.105 Uiso 0.30(4) 1 d PR C 2 C181 C 0.2586(6) 0.1930(3) 0.3860(7) 0.084(3) Uani 0.615(11) 1 d P D 1 H18A H 0.1681 0.2028 0.3032 0.126 Uiso 0.615(11) 1 calc PR D 1 H18B H 0.2918 0.1682 0.3536 0.126 Uiso 0.615(11) 1 calc PR D 1 H18C H 0.3442 0.2117 0.4051 0.126 Uiso 0.615(11) 1 calc PR D 1 C182 C 0.2355(11) 0.2260(5) 0.486(2) 0.144(10) Uani 0.385(11) 1 d P D 2 H18D H 0.1504 0.2329 0.3916 0.216 Uiso 0.385(11) 1 calc PR D 2 H18E H 0.3355 0.2288 0.4647 0.216 Uiso 0.385(11) 1 calc PR D 2 H18F H 0.2334 0.2432 0.5716 0.216 Uiso 0.385(11) 1 calc PR D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.04299(18) 0.03082(16) 0.04183(17) 0.00029(11) 0.01474(13) -0.00090(11) Cu2 0.04081(18) 0.03061(16) 0.04188(16) 0.00026(11) 0.01434(12) -0.00275(11) O1 0.0520(9) 0.0373(9) 0.0488(9) -0.0053(7) 0.0122(7) -0.0132(7) O2 0.0512(9) 0.0375(9) 0.0448(8) 0.0063(7) 0.0074(7) -0.0015(7) O3 0.0574(10) 0.0411(10) 0.0497(9) -0.0001(7) 0.0047(8) 0.0051(8) O4 0.0507(10) 0.0451(10) 0.0570(10) -0.0108(8) 0.0069(8) -0.0060(8) O5 0.0477(10) 0.0465(10) 0.0515(9) -0.0062(8) 0.0153(8) -0.0161(7) O6 0.0591(11) 0.0627(12) 0.0648(11) -0.0053(9) 0.0339(9) 0.0013(9) O7 0.0484(9) 0.0486(10) 0.0576(10) -0.0093(8) 0.0247(8) -0.0115(8) O8 0.0571(10) 0.0437(10) 0.0532(10) -0.0145(8) 0.0133(8) -0.0162(8) O9 0.0518(10) 0.0423(9) 0.0508(9) 0.0176(7) 0.0102(7) 0.0043(8) O10 0.0692(12) 0.0598(11) 0.0557(10) 0.0043(8) 0.0358(9) 0.0020(9) O11 0.0515(10) 0.0426(9) 0.0543(9) -0.0126(7) 0.0167(8) -0.0143(8) O12 0.0547(10) 0.0476(10) 0.0497(9) -0.0080(7) 0.0240(8) -0.0120(8) C1 0.0396(12) 0.0372(12) 0.0370(11) 0.0004(10) 0.0181(10) -0.0024(10) C2 0.0392(12) 0.0389(13) 0.0411(12) -0.0030(10) 0.0168(10) -0.0028(10) C3 0.0395(12) 0.0358(12) 0.0424(12) -0.0007(10) 0.0091(10) -0.0020(10) C4 0.0374(12) 0.0399(13) 0.0401(12) 0.0043(10) 0.0102(10) 0.0016(10) C5 0.0425(13) 0.0369(12) 0.0359(11) 0.0050(9) 0.0089(10) -0.0054(10) C6 0.0418(12) 0.0350(12) 0.0385(11) 0.0012(9) 0.0098(10) -0.0040(10) N1 0.0718(15) 0.0650(15) 0.0373(11) 0.0143(10) 0.0079(10) -0.0145(11) C7 0.111(2) 0.075(2) 0.0468(15) -0.0031(14) 0.0349(16) -0.0091(17) C8 0.160(3) 0.0539(19) 0.082(2) 0.0100(16) 0.058(2) 0.009(2) C9 0.112(3) 0.069(2) 0.091(2) 0.0165(17) 0.048(2) 0.0171(19) C10 0.075(3) 0.161(4) 0.162(4) 0.064(3) 0.031(3) -0.005(3) C111 0.078(8) 0.086(8) 0.041(6) 0.005(4) 0.018(4) -0.004(6) C112 0.067(6) 0.082(6) 0.040(5) -0.002(4) 0.012(3) -0.020(4) C121 0.109(8) 0.096(9) 0.073(5) 0.021(5) -0.009(5) -0.046(7) C122 0.066(5) 0.121(11) 0.049(4) 0.012(5) 0.013(3) -0.022(6) N2 0.0391(11) 0.0677(15) 0.0687(14) 0.0121(11) 0.0119(10) -0.0142(10) C13 0.086(2) 0.080(2) 0.088(2) -0.0092(17) 0.0313(19) -0.0173(18) C14 0.147(4) 0.177(4) 0.072(2) 0.015(3) 0.015(2) -0.062(3) C15 0.0536(17) 0.074(2) 0.116(3) 0.0071(18) 0.0360(17) -0.0006(15) C16 0.077(2) 0.058(2) 0.188(4) -0.016(2) 0.059(2) -0.0118(17) C17 0.0591(19) 0.103(3) 0.086(2) 0.029(2) -0.0003(17) -0.0171(18) C181 0.053(3) 0.123(7) 0.070(4) 0.014(4) 0.012(3) -0.013(3) C182 0.073(7) 0.122(13) 0.187(17) 0.101(12) -0.033(9) -0.031(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O3 1.9854(16) . ? Cu1 O7 1.9928(15) . ? Cu1 O8 2.0637(16) 4_565 ? Cu1 O5 2.0830(16) . ? Cu1 O1 2.1479(16) . ? Cu1 O6 2.2013(18) 4_565 ? Cu2 O2 1.9740(15) . ? Cu2 O12 1.9880(15) 3_656 ? Cu2 O11 2.0704(16) . ? Cu2 O9 2.0857(16) . ? Cu2 O4 2.1701(17) . ? Cu2 O10 2.2024(17) 3_756 ? O1 C1 1.233(2) . ? O2 C1 1.247(2) . ? O3 C2 1.247(3) . ? O4 C2 1.235(3) . ? O5 C4 1.259(3) . ? O6 C4 1.232(3) . ? O6 Cu1 2.2013(18) 4_566 ? O7 C3 1.244(3) . ? O8 C3 1.239(2) . ? O8 Cu1 2.0637(16) 4_566 ? O9 C5 1.258(3) . ? O10 C5 1.230(3) . ? O10 Cu2 2.2024(17) 3_756 ? O11 C6 1.240(2) . ? O12 C6 1.249(3) . ? O12 Cu2 1.9880(15) 3_656 ? C1 C2 1.562(3) . ? C3 C4 1.550(3) . ? C5 C5 1.562(4) 3_756 ? C6 C6 1.551(4) 3_656 ? N1 C7 1.495(3) . ? N1 C9 1.500(4) . ? N1 C112 1.516(10) . ? N1 C111 1.532(14) . ? C7 C8 1.503(3) . ? C9 C10 1.478(4) . ? C111 C121 1.48(2) . ? C112 C122 1.48(2) . ? N2 C13 1.486(3) . ? N2 C17 1.494(3) . ? N2 C15 1.498(3) . ? C13 C14 1.503(4) . ? C15 C16 1.496(4) . ? C17 C182 1.369(12) . ? C17 C181 1.406(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 Cu1 O7 174.88(6) . . ? O3 Cu1 O8 92.43(7) . 4_565 ? O7 Cu1 O8 92.05(6) . 4_565 ? O3 Cu1 O5 94.78(6) . . ? O7 Cu1 O5 81.21(6) . . ? O8 Cu1 O5 168.22(7) 4_565 . ? O3 Cu1 O1 81.06(7) . . ? O7 Cu1 O1 95.85(6) . . ? O8 Cu1 O1 98.05(6) 4_565 . ? O5 Cu1 O1 92.28(6) . . ? O3 Cu1 O6 94.12(7) . 4_565 ? O7 Cu1 O6 89.17(8) . 4_565 ? O8 Cu1 O6 78.89(6) 4_565 4_565 ? O5 Cu1 O6 91.29(6) . 4_565 ? O1 Cu1 O6 174.23(6) . 4_565 ? O2 Cu2 O12 177.30(6) . 3_656 ? O2 Cu2 O11 95.30(6) . . ? O12 Cu2 O11 82.34(6) 3_656 . ? O2 Cu2 O9 92.50(6) . . ? O12 Cu2 O9 90.00(6) 3_656 . ? O11 Cu2 O9 169.79(7) . . ? O2 Cu2 O4 80.88(6) . . ? O12 Cu2 O4 97.90(6) 3_656 . ? O11 Cu2 O4 92.82(6) . . ? O9 Cu2 O4 94.91(6) . . ? O2 Cu2 O10 92.67(6) . 3_756 ? O12 Cu2 O10 88.85(8) 3_656 3_756 ? O11 Cu2 O10 95.08(6) . 3_756 ? O9 Cu2 O10 77.95(6) . 3_756 ? O4 Cu2 O10 170.23(6) . 3_756 ? C1 O1 Cu1 109.51(14) . . ? C1 O2 Cu2 115.32(14) . . ? C2 O3 Cu1 115.01(14) . . ? C2 O4 Cu2 109.27(14) . . ? C4 O5 Cu1 111.05(13) . . ? C4 O6 Cu1 109.35(15) . 4_566 ? C3 O7 Cu1 114.24(14) . . ? C3 O8 Cu1 114.59(14) . 4_566 ? C5 O9 Cu2 114.76(13) . . ? C5 O10 Cu2 110.35(14) . 3_756 ? C6 O11 Cu2 110.42(13) . . ? C6 O12 Cu2 113.18(13) . 3_656 ? O1 C1 O2 126.0(2) . . ? O1 C1 C2 117.36(18) . . ? O2 C1 C2 116.61(18) . . ? O4 C2 O3 126.5(2) . . ? O4 C2 C1 117.16(19) . . ? O3 C2 C1 116.37(18) . . ? O8 C3 O7 126.3(2) . . ? O8 C3 C4 117.2(2) . . ? O7 C3 C4 116.48(19) . . ? O6 C4 O5 125.3(2) . . ? O6 C4 C3 118.9(2) . . ? O5 C4 C3 115.86(19) . . ? O10 C5 O9 125.60(19) . . ? O10 C5 C5 118.6(2) . 3_756 ? O9 C5 C5 115.8(2) . 3_756 ? O11 C6 O12 126.4(2) . . ? O11 C6 C6 117.2(2) . 3_656 ? O12 C6 C6 116.4(2) . 3_656 ? C7 N1 C9 114.0(2) . . ? C7 N1 C112 120.3(7) . . ? C9 N1 C112 99.7(9) . . ? C7 N1 C111 101.4(9) . . ? C9 N1 C111 124.7(10) . . ? C112 N1 C111 25.3(4) . . ? N1 C7 C8 114.6(2) . . ? C10 C9 N1 114.2(3) . . ? C121 C111 N1 110.7(14) . . ? C122 C112 N1 110.8(12) . . ? C13 N2 C17 109.3(3) . . ? C13 N2 C15 114.6(2) . . ? C17 N2 C15 113.8(3) . . ? N2 C13 C14 114.1(3) . . ? C16 C15 N2 114.5(2) . . ? C182 C17 C181 64.0(8) . . ? C182 C17 N2 116.7(5) . . ? C181 C17 N2 119.2(4) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.337 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.048