# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Codd, Rachel' _publ_contact_author_email rachel.codd@sydney.edu.au _publ_section_title ; Structural diversity of complexes between Cu(II) or Ni(II) and endocyclic oxygen- or nitrogen-containing ligands: Synthesis, X-ray structure determinations and circular dichroism spectra ; loop_ _publ_author_name M.Fainerman-Melnikova J.Clegg A.Pakchung P.Jensen R.Codd # Attachment '- combined.CIF' data_rc08jc8s _database_code_depnum_ccdc_archive 'CCDC 780209' #TrackingRef '- combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H15 Cu N3 O5, C14 H6 Cu N2 O8, 3(H2 O)' _chemical_formula_sum 'C31 H27 Cu2 N5 O16' _chemical_formula_weight 852.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9530(9) _cell_length_b 12.2882(11) _cell_length_c 14.1263(12) _cell_angle_alpha 89.826(1) _cell_angle_beta 76.541(1) _cell_angle_gamma 75.689(1) _cell_volume 1625.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 11432 _cell_measurement_theta_min 2.203 _cell_measurement_theta_max 28.340 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.742 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 868 _exptl_absorpt_coefficient_mu 1.397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6627 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 281 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.23 _diffrn_reflns_number 16238 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 28.34 _reflns_number_total 7561 _reflns_number_gt 6924 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _refine_special_details ; The O-bound H atoms were refined with bond length restraints of 0.84(1) \A. 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^)+(0.0424P)^2^+0.6396P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7561 _refine_ls_number_parameters 517 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0277 _refine_ls_R_factor_gt 0.0248 _refine_ls_wR_factor_ref 0.0713 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.50209(15) 0.12138(12) 0.83154(10) 0.0169(3) Uani 1 1 d . . . C2 C 0.45471(15) 0.21478(12) 0.91088(10) 0.0159(3) Uani 1 1 d . . . C3 C 0.38367(15) 0.40694(12) 0.94400(10) 0.0159(3) Uani 1 1 d . . . C4 C 0.35201(16) 0.39383(12) 1.04361(11) 0.0202(3) Uani 1 1 d . . . H4 H 0.3140 0.4576 1.0884 0.024 Uiso 1 1 calc R . . C5 C 0.37689(17) 0.28571(13) 1.07688(11) 0.0223(3) Uani 1 1 d . . . H5 H 0.3585 0.2745 1.1448 0.027 Uiso 1 1 calc R . . C6 C 0.42906(16) 0.19461(12) 1.00926(11) 0.0196(3) Uani 1 1 d . . . H6 H 0.4469 0.1199 1.0299 0.024 Uiso 1 1 calc R . . C7 C 0.36688(15) 0.52059(12) 0.90111(10) 0.0168(3) Uani 1 1 d . . . C8 C 0.72312(15) 0.39117(12) 0.62598(10) 0.0174(3) Uani 1 1 d . . . C9 C 0.84141(17) 0.43545(14) 0.60742(12) 0.0268(3) Uani 1 1 d . . . H9 H 0.8713 0.4655 0.5463 0.032 Uiso 1 1 calc R . . C10 C 0.91548(18) 0.43523(16) 0.67951(13) 0.0316(4) Uani 1 1 d . . . H10 H 0.9956 0.4666 0.6689 0.038 Uiso 1 1 calc R . . C11 C 0.87136(17) 0.38895(14) 0.76672(12) 0.0270(3) Uani 1 1 d . . . H11 H 0.9232 0.3847 0.8158 0.032 Uiso 1 1 calc R . . C12 C 0.74996(16) 0.34874(13) 0.78158(11) 0.0219(3) Uani 1 1 d . . . H12 H 0.7189 0.3176 0.8419 0.026 Uiso 1 1 calc R . . C13 C 0.64275(15) 0.37801(11) 0.55240(10) 0.0159(3) Uani 1 1 d . . . C14 C 0.44568(16) 0.32308(12) 0.52774(11) 0.0192(3) Uani 1 1 d . . . H14 H 0.3613 0.2992 0.5535 0.023 Uiso 1 1 calc R . . C15 C 0.48626(17) 0.33407(12) 0.42822(11) 0.0219(3) Uani 1 1 d . . . H15 H 0.4309 0.3175 0.3864 0.026 Uiso 1 1 calc R . . C16 C 0.60864(17) 0.36953(12) 0.39072(11) 0.0224(3) Uani 1 1 d . . . H16 H 0.6379 0.3786 0.3228 0.027 Uiso 1 1 calc R . . C17 C 0.68824(16) 0.39168(12) 0.45401(11) 0.0205(3) Uani 1 1 d . . . H17 H 0.7728 0.4159 0.4298 0.025 Uiso 1 1 calc R . . C18 C 1.12192(15) 0.19719(12) 0.43682(11) 0.0188(3) Uani 1 1 d . . . C19 C 0.98520(14) 0.15862(11) 0.47098(10) 0.0152(3) Uani 1 1 d . . . C20 C 0.80080(14) 0.10747(11) 0.42225(10) 0.0155(3) Uani 1 1 d . . . C21 C 0.74331(15) 0.08205(12) 0.51620(10) 0.0180(3) Uani 1 1 d . . . H21 H 0.6592 0.0556 0.5303 0.022 Uiso 1 1 calc R . . C22 C 0.81068(15) 0.09579(12) 0.58961(10) 0.0186(3) Uani 1 1 d . . . H22 H 0.7738 0.0782 0.6545 0.022 Uiso 1 1 calc R . . C23 C 0.93310(15) 0.13568(12) 0.56658(10) 0.0173(3) Uani 1 1 d . . . H23 H 0.9801 0.1469 0.6157 0.021 Uiso 1 1 calc R . . C24 C 0.73202(15) 0.09877(11) 0.33798(10) 0.0176(3) Uani 1 1 d . . . C25 C 1.14519(16) -0.01207(12) 0.12595(10) 0.0180(3) Uani 1 1 d . . . C26 C 1.11676(15) 0.09280(12) 0.06833(10) 0.0163(3) Uani 1 1 d . . . C27 C 1.02478(14) 0.28786(12) 0.09133(10) 0.0155(3) Uani 1 1 d . . . C28 C 1.04765(16) 0.30060(12) -0.00840(11) 0.0191(3) Uani 1 1 d . . . H28 H 1.0254 0.3729 -0.0336 0.023 Uiso 1 1 calc R . . C29 C 1.10441(17) 0.20376(13) -0.07050(11) 0.0220(3) Uani 1 1 d . . . H29 H 1.1188 0.2094 -0.1390 0.026 Uiso 1 1 calc R . . C30 C 1.14017(16) 0.09839(12) -0.03207(11) 0.0206(3) Uani 1 1 d . . . H30 H 1.1796 0.0321 -0.0738 0.025 Uiso 1 1 calc R . . C31 C 0.95496(14) 0.38025(12) 0.17180(10) 0.0156(3) Uani 1 1 d . . . N1 N 0.43463(12) 0.31883(10) 0.87872(8) 0.0146(2) Uani 1 1 d . . . N2 N 0.67524(12) 0.35241(10) 0.71369(9) 0.0162(2) Uani 1 1 d . . . N3 N 0.52182(13) 0.34506(10) 0.58890(8) 0.0157(2) Uani 1 1 d . . . N4 N 0.91993(12) 0.14466(9) 0.40055(8) 0.0137(2) Uani 1 1 d . . . N5 N 1.06007(12) 0.18666(10) 0.12607(8) 0.0147(2) Uani 1 1 d . . . O1 O 0.52243(13) 0.02259(9) 0.86214(8) 0.0231(2) Uani 1 1 d D . . O2 O 0.51291(11) 0.14666(8) 0.74578(7) 0.0201(2) Uani 1 1 d . . . O3 O 0.40724(12) 0.52818(8) 0.81352(7) 0.0202(2) Uani 1 1 d . . . O4 O 0.30907(12) 0.60363(9) 0.96611(8) 0.0225(2) Uani 1 1 d . . . O5 O 1.18099(13) 0.22227(11) 0.49860(8) 0.0307(3) Uani 1 1 d . . . O6 O 1.16568(11) 0.19864(9) 0.34515(7) 0.0223(2) Uani 1 1 d . . . O7 O 0.78523(12) 0.13550(9) 0.25919(8) 0.0218(2) Uani 1 1 d . . . O8 O 0.62676(12) 0.05651(10) 0.35605(9) 0.0261(2) Uani 1 1 d . . . O9 O 1.20297(13) -0.10481(9) 0.08149(8) 0.0263(2) Uani 1 1 d . . . O10 O 1.10525(12) 0.00621(9) 0.21812(7) 0.0217(2) Uani 1 1 d . . . O11 O 0.93206(11) 0.34673(9) 0.25748(7) 0.0194(2) Uani 1 1 d . . . O12 O 0.92560(11) 0.47936(8) 0.14754(8) 0.0199(2) Uani 1 1 d . . . O1W O 0.26983(11) 0.36194(10) 0.73345(8) 0.0203(2) Uani 1 1 d . . . O2W O 0.20783(13) 0.17757(9) 0.68142(8) 0.0242(2) Uani 1 1 d D . . O3W O 0.43503(12) 0.12897(9) 0.26059(8) 0.0192(2) Uani 1 1 d . . . O4W O 0.70840(15) 0.20701(9) 0.09349(9) 0.0288(3) Uani 1 1 d . . . Cu1 Cu 0.473979(17) 0.334986(13) 0.732731(11) 0.01411(5) Uani 1 1 d . . . Cu2 Cu 1.003004(18) 0.170647(13) 0.263714(11) 0.01490(5) Uani 1 1 d . . . H1O H 0.5409(19) -0.0224(12) 0.8135(8) 0.022 Uiso 1 1 d D . . H2O H 0.306(2) 0.6650(16) 0.9406(14) 0.022 Uiso 1 1 d . . . H3O H 0.212(2) 0.4080(16) 0.7675(14) 0.022 Uiso 1 1 d . . . H4O H 0.244(2) 0.3055(17) 0.7267(14) 0.022 Uiso 1 1 d . . . H5O H 0.198(2) 0.1848(16) 0.6285(15) 0.022 Uiso 1 1 d . . . H6O H 0.2696(14) 0.1162(8) 0.6774(13) 0.022 Uiso 1 1 d D . . H7O H 0.491(2) 0.1107(16) 0.2925(14) 0.022 Uiso 1 1 d . . . H8O H 0.356(2) 0.1477(16) 0.2910(14) 0.022 Uiso 1 1 d . . . H9O H 0.740(2) 0.1663(16) 0.0486(15) 0.022 Uiso 1 1 d . . . H10O H 0.725(2) 0.1841(16) 0.1417(15) 0.022 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0166(6) 0.0161(6) 0.0176(7) 0.0010(5) -0.0040(5) -0.0033(5) C2 0.0160(6) 0.0158(6) 0.0159(6) 0.0024(5) -0.0042(5) -0.0037(5) C3 0.0168(6) 0.0159(6) 0.0150(6) 0.0009(5) -0.0042(5) -0.0038(5) C4 0.0257(7) 0.0186(7) 0.0151(7) -0.0014(5) -0.0046(6) -0.0038(6) C5 0.0304(8) 0.0238(7) 0.0121(6) 0.0039(5) -0.0055(6) -0.0053(6) C6 0.0240(7) 0.0177(7) 0.0171(7) 0.0054(5) -0.0058(5) -0.0045(5) C7 0.0183(6) 0.0151(6) 0.0176(7) 0.0001(5) -0.0065(5) -0.0035(5) C8 0.0176(6) 0.0151(6) 0.0179(7) -0.0003(5) -0.0026(5) -0.0030(5) C9 0.0245(8) 0.0328(8) 0.0255(8) 0.0046(6) -0.0035(6) -0.0142(7) C10 0.0229(8) 0.0402(10) 0.0366(9) -0.0002(7) -0.0076(7) -0.0163(7) C11 0.0212(7) 0.0335(9) 0.0274(8) -0.0045(7) -0.0102(6) -0.0049(6) C12 0.0216(7) 0.0259(7) 0.0173(7) -0.0010(6) -0.0054(6) -0.0034(6) C13 0.0182(6) 0.0128(6) 0.0149(6) 0.0010(5) -0.0025(5) -0.0020(5) C14 0.0214(7) 0.0181(7) 0.0186(7) 0.0004(5) -0.0070(5) -0.0043(5) C15 0.0289(8) 0.0197(7) 0.0162(7) -0.0011(5) -0.0096(6) -0.0004(6) C16 0.0309(8) 0.0182(7) 0.0126(6) 0.0024(5) -0.0035(6) 0.0021(6) C17 0.0223(7) 0.0172(7) 0.0183(7) 0.0027(5) -0.0007(6) -0.0024(5) C18 0.0173(6) 0.0200(7) 0.0188(7) 0.0011(5) -0.0047(5) -0.0040(5) C19 0.0154(6) 0.0146(6) 0.0141(6) -0.0014(5) -0.0042(5) -0.0004(5) C20 0.0162(6) 0.0129(6) 0.0169(6) 0.0010(5) -0.0058(5) -0.0010(5) C21 0.0168(6) 0.0167(6) 0.0195(7) 0.0037(5) -0.0040(5) -0.0026(5) C22 0.0200(7) 0.0184(7) 0.0139(6) 0.0030(5) -0.0021(5) -0.0002(5) C23 0.0179(6) 0.0175(7) 0.0150(6) -0.0012(5) -0.0056(5) 0.0000(5) C24 0.0193(6) 0.0149(6) 0.0192(7) 0.0014(5) -0.0088(5) -0.0013(5) C25 0.0218(7) 0.0165(6) 0.0154(7) 0.0024(5) -0.0059(5) -0.0030(5) C26 0.0179(6) 0.0154(6) 0.0147(6) 0.0008(5) -0.0033(5) -0.0033(5) C27 0.0147(6) 0.0161(6) 0.0154(6) 0.0015(5) -0.0032(5) -0.0039(5) C28 0.0220(7) 0.0175(7) 0.0162(7) 0.0039(5) -0.0028(5) -0.0039(5) C29 0.0286(8) 0.0223(7) 0.0130(7) 0.0023(5) -0.0028(6) -0.0047(6) C30 0.0257(7) 0.0184(7) 0.0151(7) -0.0011(5) -0.0019(6) -0.0036(6) C31 0.0137(6) 0.0165(6) 0.0160(6) -0.0002(5) -0.0024(5) -0.0040(5) N1 0.0159(5) 0.0151(5) 0.0122(5) 0.0015(4) -0.0026(4) -0.0037(4) N2 0.0168(5) 0.0162(5) 0.0146(5) -0.0010(4) -0.0031(4) -0.0028(4) N3 0.0188(6) 0.0150(5) 0.0126(5) 0.0009(4) -0.0036(4) -0.0033(4) N4 0.0145(5) 0.0128(5) 0.0127(5) 0.0005(4) -0.0036(4) -0.0011(4) N5 0.0160(5) 0.0150(5) 0.0128(5) 0.0011(4) -0.0030(4) -0.0034(4) O1 0.0362(6) 0.0130(5) 0.0183(5) 0.0015(4) -0.0066(5) -0.0030(4) O2 0.0278(5) 0.0161(5) 0.0147(5) 0.0018(4) -0.0029(4) -0.0045(4) O3 0.0284(5) 0.0169(5) 0.0145(5) 0.0025(4) -0.0047(4) -0.0047(4) O4 0.0334(6) 0.0139(5) 0.0178(5) -0.0004(4) -0.0047(4) -0.0029(4) O5 0.0307(6) 0.0487(7) 0.0217(6) 0.0023(5) -0.0117(5) -0.0217(6) O6 0.0180(5) 0.0332(6) 0.0165(5) 0.0019(4) -0.0040(4) -0.0082(4) O7 0.0245(5) 0.0268(5) 0.0169(5) 0.0035(4) -0.0098(4) -0.0074(4) O8 0.0266(6) 0.0292(6) 0.0314(6) 0.0093(5) -0.0163(5) -0.0146(5) O9 0.0401(6) 0.0150(5) 0.0192(5) -0.0020(4) -0.0068(5) 0.0009(4) O10 0.0308(6) 0.0177(5) 0.0134(5) 0.0019(4) -0.0051(4) -0.0003(4) O11 0.0231(5) 0.0182(5) 0.0150(5) 0.0006(4) -0.0024(4) -0.0039(4) O12 0.0222(5) 0.0142(5) 0.0208(5) 0.0013(4) -0.0016(4) -0.0031(4) O1W 0.0165(5) 0.0193(5) 0.0233(5) -0.0062(4) -0.0023(4) -0.0035(4) O2W 0.0304(6) 0.0228(5) 0.0215(5) -0.0006(4) -0.0100(5) -0.0070(5) O3W 0.0162(5) 0.0214(5) 0.0192(5) 0.0012(4) -0.0048(4) -0.0030(4) O4W 0.0520(8) 0.0162(5) 0.0162(5) 0.0002(4) -0.0134(5) 0.0000(5) Cu1 0.01565(9) 0.01622(9) 0.01054(9) 0.00150(6) -0.00264(6) -0.00469(6) Cu2 0.01828(9) 0.01496(9) 0.01035(9) 0.00093(6) -0.00342(6) -0.00218(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.2366(18) . ? C1 O1 1.2718(17) . ? C1 C2 1.5133(19) . ? C2 N1 1.3392(18) . ? C2 C6 1.3863(19) . ? C3 N1 1.3406(18) . ? C3 C4 1.387(2) . ? C3 C7 1.5073(19) . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C5 C6 1.387(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O3 1.2196(18) . ? C7 O4 1.2980(17) . ? C8 N2 1.3502(18) . ? C8 C9 1.387(2) . ? C8 C13 1.483(2) . ? C9 C10 1.389(2) . ? C9 H9 0.9500 . ? C10 C11 1.379(2) . ? C10 H10 0.9500 . ? C11 C12 1.387(2) . ? C11 H11 0.9500 . ? C12 N2 1.3380(19) . ? C12 H12 0.9500 . ? C13 N3 1.3526(18) . ? C13 C17 1.381(2) . ? C14 N3 1.3420(18) . ? C14 C15 1.385(2) . ? C14 H14 0.9500 . ? C15 C16 1.384(2) . ? C15 H15 0.9500 . ? C16 C17 1.392(2) . ? C16 H16 0.9500 . ? C17 H17 0.9500 . ? C18 O5 1.2379(18) . ? C18 O6 1.2681(18) . ? C18 C19 1.5235(19) . ? C19 N4 1.3411(17) . ? C19 C23 1.384(2) . ? C20 N4 1.3441(18) . ? C20 C21 1.3852(19) . ? C20 C24 1.5211(19) . ? C21 C22 1.391(2) . ? C21 H21 0.9500 . ? C22 C23 1.393(2) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 O7 1.2505(18) . ? C24 O8 1.2554(18) . ? C25 O9 1.2393(18) . ? C25 O10 1.2730(17) . ? C25 C26 1.5244(19) . ? C26 N5 1.3356(18) . ? C26 C30 1.387(2) . ? C27 N5 1.3309(18) . ? C27 C28 1.3885(19) . ? C27 C31 1.5212(19) . ? C28 C29 1.396(2) . ? C28 H28 0.9500 . ? C29 C30 1.398(2) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 O12 1.2466(17) . ? C31 O11 1.2655(17) . ? N1 Cu1 2.0262(12) . ? N2 Cu1 2.0228(12) . ? N3 Cu1 1.9869(12) . ? N4 Cu2 1.9761(12) . ? N5 Cu2 1.9185(12) . ? O1 H1O 0.840(12) . ? O2 Cu1 2.2643(10) . ? O4 H2O 0.832(19) . ? O6 Cu2 2.2821(10) . ? O7 Cu2 2.3272(11) . ? O10 Cu2 2.0541(10) . ? O11 Cu2 2.1120(10) . ? O1W Cu1 1.9738(11) . ? O1W H3O 0.77(2) . ? O1W H4O 0.81(2) . ? O2W H5O 0.78(2) . ? O2W H6O 0.840(12) . ? O3W H7O 0.79(2) . ? O3W H8O 0.78(2) . ? O4W H9O 0.76(2) . ? O4W H10O 0.77(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 126.58(14) . . ? O2 C1 C2 118.74(12) . . ? O1 C1 C2 114.64(12) . . ? N1 C2 C6 122.50(13) . . ? N1 C2 C1 114.71(12) . . ? C6 C2 C1 122.75(13) . . ? N1 C3 C4 122.16(13) . . ? N1 C3 C7 115.06(12) . . ? C4 C3 C7 122.76(13) . . ? C3 C4 C5 118.88(14) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C6 C5 C4 118.89(13) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C2 C6 C5 118.69(13) . . ? C2 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? O3 C7 O4 126.25(13) . . ? O3 C7 C3 120.52(13) . . ? O4 C7 C3 113.22(12) . . ? N2 C8 C9 121.45(14) . . ? N2 C8 C13 114.52(12) . . ? C9 C8 C13 123.99(13) . . ? C8 C9 C10 118.99(15) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 119.21(15) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 118.87(15) . . ? C10 C11 H11 120.6 . . ? C12 C11 H11 120.6 . . ? N2 C12 C11 122.13(14) . . ? N2 C12 H12 118.9 . . ? C11 C12 H12 118.9 . . ? N3 C13 C17 121.61(13) . . ? N3 C13 C8 114.03(12) . . ? C17 C13 C8 124.28(13) . . ? N3 C14 C15 122.07(14) . . ? N3 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C16 C15 C14 118.99(14) . . ? C16 C15 H15 120.5 . . ? C14 C15 H15 120.5 . . ? C15 C16 C17 118.99(14) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C13 C17 C16 119.18(14) . . ? C13 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? O5 C18 O6 126.00(14) . . ? O5 C18 C19 118.81(13) . . ? O6 C18 C19 115.18(12) . . ? N4 C19 C23 121.69(13) . . ? N4 C19 C18 114.96(12) . . ? C23 C19 C18 123.31(13) . . ? N4 C20 C21 121.58(13) . . ? N4 C20 C24 115.66(12) . . ? C21 C20 C24 122.73(13) . . ? C20 C21 C22 118.97(13) . . ? C20 C21 H21 120.5 . . ? C22 C21 H21 120.5 . . ? C21 C22 C23 119.00(13) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C19 C23 C22 118.92(13) . . ? C19 C23 H23 120.5 . . ? C22 C23 H23 120.5 . . ? O7 C24 O8 127.39(13) . . ? O7 C24 C20 116.65(12) . . ? O8 C24 C20 115.96(13) . . ? O9 C25 O10 126.16(13) . . ? O9 C25 C26 119.30(13) . . ? O10 C25 C26 114.54(12) . . ? N5 C26 C30 120.01(13) . . ? N5 C26 C25 112.38(12) . . ? C30 C26 C25 127.59(13) . . ? N5 C27 C28 120.80(13) . . ? N5 C27 C31 112.50(12) . . ? C28 C27 C31 126.66(13) . . ? C27 C28 C29 117.87(13) . . ? C27 C28 H28 121.1 . . ? C29 C28 H28 121.1 . . ? C28 C29 C30 120.15(13) . . ? C28 C29 H29 119.9 . . ? C30 C29 H29 119.9 . . ? C26 C30 C29 118.54(13) . . ? C26 C30 H30 120.7 . . ? C29 C30 H30 120.7 . . ? O12 C31 O11 126.93(13) . . ? O12 C31 C27 117.86(12) . . ? O11 C31 C27 115.21(12) . . ? C2 N1 C3 118.83(12) . . ? C2 N1 Cu1 117.97(9) . . ? C3 N1 Cu1 123.12(9) . . ? C12 N2 C8 119.14(13) . . ? C12 N2 Cu1 127.31(10) . . ? C8 N2 Cu1 112.44(9) . . ? C14 N3 C13 119.15(12) . . ? C14 N3 Cu1 126.07(10) . . ? C13 N3 Cu1 114.78(9) . . ? C19 N4 C20 119.83(12) . . ? C19 N4 Cu2 120.52(9) . . ? C20 N4 Cu2 119.57(9) . . ? C27 N5 C26 122.60(12) . . ? C27 N5 Cu2 119.14(9) . . ? C26 N5 Cu2 117.63(9) . . ? C1 O1 H1O 107.2(13) . . ? C1 O2 Cu1 111.55(9) . . ? C7 O4 H2O 110.8(13) . . ? C18 O6 Cu2 112.49(9) . . ? C24 O7 Cu2 110.42(9) . . ? C25 O10 Cu2 114.45(9) . . ? C31 O11 Cu2 113.67(9) . . ? Cu1 O1W H3O 121.6(14) . . ? Cu1 O1W H4O 114.7(13) . . ? H3O O1W H4O 113.2(19) . . ? H5O O2W H6O 103.9(18) . . ? H7O O3W H8O 113.8(19) . . ? H9O O4W H10O 116(2) . . ? O1W Cu1 N3 90.15(5) . . ? O1W Cu1 N2 162.79(5) . . ? N3 Cu1 N2 80.91(5) . . ? O1W Cu1 N1 92.23(5) . . ? N3 Cu1 N1 177.12(5) . . ? N2 Cu1 N1 97.19(5) . . ? O1W Cu1 O2 95.70(4) . . ? N3 Cu1 O2 101.35(4) . . ? N2 Cu1 O2 100.45(4) . . ? N1 Cu1 O2 76.80(4) . . ? N5 Cu2 N4 170.88(5) . . ? N5 Cu2 O10 80.30(5) . . ? N4 Cu2 O10 97.62(4) . . ? N5 Cu2 O11 79.18(4) . . ? N4 Cu2 O11 103.18(4) . . ? O10 Cu2 O11 159.20(4) . . ? N5 Cu2 O6 112.91(4) . . ? N4 Cu2 O6 76.08(4) . . ? O10 Cu2 O6 95.98(4) . . ? O11 Cu2 O6 88.92(4) . . ? N5 Cu2 O7 94.92(4) . . ? N4 Cu2 O7 76.15(4) . . ? O10 Cu2 O7 90.08(4) . . ? O11 Cu2 O7 94.99(4) . . ? O6 Cu2 O7 152.12(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 N1 -2.86(19) . . . . ? O1 C1 C2 N1 179.36(12) . . . . ? O2 C1 C2 C6 174.92(14) . . . . ? O1 C1 C2 C6 -2.9(2) . . . . ? N1 C3 C4 C5 1.4(2) . . . . ? C7 C3 C4 C5 -177.08(13) . . . . ? C3 C4 C5 C6 -1.6(2) . . . . ? N1 C2 C6 C5 1.8(2) . . . . ? C1 C2 C6 C5 -175.78(14) . . . . ? C4 C5 C6 C2 0.1(2) . . . . ? N1 C3 C7 O3 -4.8(2) . . . . ? C4 C3 C7 O3 173.80(14) . . . . ? N1 C3 C7 O4 175.96(12) . . . . ? C4 C3 C7 O4 -5.4(2) . . . . ? N2 C8 C9 C10 2.8(2) . . . . ? C13 C8 C9 C10 -174.72(15) . . . . ? C8 C9 C10 C11 1.3(3) . . . . ? C9 C10 C11 C12 -3.0(3) . . . . ? C10 C11 C12 N2 0.7(2) . . . . ? N2 C8 C13 N3 9.43(18) . . . . ? C9 C8 C13 N3 -172.88(14) . . . . ? N2 C8 C13 C17 -167.25(13) . . . . ? C9 C8 C13 C17 10.4(2) . . . . ? N3 C14 C15 C16 -0.4(2) . . . . ? C14 C15 C16 C17 0.8(2) . . . . ? N3 C13 C17 C16 -0.9(2) . . . . ? C8 C13 C17 C16 175.57(13) . . . . ? C15 C16 C17 C13 -0.2(2) . . . . ? O5 C18 C19 N4 173.20(13) . . . . ? O6 C18 C19 N4 -7.84(18) . . . . ? O5 C18 C19 C23 -8.9(2) . . . . ? O6 C18 C19 C23 170.10(13) . . . . ? N4 C20 C21 C22 0.2(2) . . . . ? C24 C20 C21 C22 -177.95(12) . . . . ? C20 C21 C22 C23 0.6(2) . . . . ? N4 C19 C23 C22 0.8(2) . . . . ? C18 C19 C23 C22 -177.01(13) . . . . ? C21 C22 C23 C19 -1.1(2) . . . . ? N4 C20 C24 O7 -5.75(18) . . . . ? C21 C20 C24 O7 172.49(13) . . . . ? N4 C20 C24 O8 175.06(12) . . . . ? C21 C20 C24 O8 -6.7(2) . . . . ? O9 C25 C26 N5 -177.18(13) . . . . ? O10 C25 C26 N5 2.83(18) . . . . ? O9 C25 C26 C30 4.3(2) . . . . ? O10 C25 C26 C30 -175.68(14) . . . . ? N5 C27 C28 C29 2.0(2) . . . . ? C31 C27 C28 C29 -175.48(13) . . . . ? C27 C28 C29 C30 -1.8(2) . . . . ? N5 C26 C30 C29 0.6(2) . . . . ? C25 C26 C30 C29 178.98(14) . . . . ? C28 C29 C30 C26 0.5(2) . . . . ? N5 C27 C31 O12 175.65(12) . . . . ? C28 C27 C31 O12 -6.7(2) . . . . ? N5 C27 C31 O11 -4.81(17) . . . . ? C28 C27 C31 O11 172.83(13) . . . . ? C6 C2 N1 C3 -2.1(2) . . . . ? C1 C2 N1 C3 175.70(12) . . . . ? C6 C2 N1 Cu1 -179.13(11) . . . . ? C1 C2 N1 Cu1 -1.35(15) . . . . ? C4 C3 N1 C2 0.4(2) . . . . ? C7 C3 N1 C2 179.04(12) . . . . ? C4 C3 N1 Cu1 177.31(11) . . . . ? C7 C3 N1 Cu1 -4.08(17) . . . . ? C11 C12 N2 C8 3.4(2) . . . . ? C11 C12 N2 Cu1 -163.53(12) . . . . ? C9 C8 N2 C12 -5.2(2) . . . . ? C13 C8 N2 C12 172.57(13) . . . . ? C9 C8 N2 Cu1 163.61(12) . . . . ? C13 C8 N2 Cu1 -18.64(15) . . . . ? C15 C14 N3 C13 -0.6(2) . . . . ? C15 C14 N3 Cu1 178.98(11) . . . . ? C17 C13 N3 C14 1.3(2) . . . . ? C8 C13 N3 C14 -175.51(12) . . . . ? C17 C13 N3 Cu1 -178.37(11) . . . . ? C8 C13 N3 Cu1 4.85(15) . . . . ? C23 C19 N4 C20 0.0(2) . . . . ? C18 C19 N4 C20 177.96(11) . . . . ? C23 C19 N4 Cu2 -176.78(10) . . . . ? C18 C19 N4 Cu2 1.19(16) . . . . ? C21 C20 N4 C19 -0.5(2) . . . . ? C24 C20 N4 C19 177.78(12) . . . . ? C21 C20 N4 Cu2 176.31(10) . . . . ? C24 C20 N4 Cu2 -5.43(15) . . . . ? C28 C27 N5 C26 -0.9(2) . . . . ? C31 C27 N5 C26 176.89(12) . . . . ? C28 C27 N5 Cu2 -171.59(10) . . . . ? C31 C27 N5 Cu2 6.21(15) . . . . ? C30 C26 N5 C27 -0.4(2) . . . . ? C25 C26 N5 C27 -179.05(12) . . . . ? C30 C26 N5 Cu2 170.41(11) . . . . ? C25 C26 N5 Cu2 -8.23(15) . . . . ? O1 C1 O2 Cu1 -177.53(12) . . . . ? C2 C1 O2 Cu1 4.98(16) . . . . ? O5 C18 O6 Cu2 -171.49(13) . . . . ? C19 C18 O6 Cu2 9.63(15) . . . . ? O8 C24 O7 Cu2 -169.14(13) . . . . ? C20 C24 O7 Cu2 11.79(15) . . . . ? O9 C25 O10 Cu2 -176.62(13) . . . . ? C26 C25 O10 Cu2 3.37(16) . . . . ? O12 C31 O11 Cu2 -179.08(11) . . . . ? C27 C31 O11 Cu2 1.44(14) . . . . ? C14 N3 Cu1 O1W -25.94(12) . . . . ? C13 N3 Cu1 O1W 153.67(10) . . . . ? C14 N3 Cu1 N2 168.83(12) . . . . ? C13 N3 Cu1 N2 -11.56(10) . . . . ? C14 N3 Cu1 O2 69.91(12) . . . . ? C13 N3 Cu1 O2 -110.48(10) . . . . ? C12 N2 Cu1 O1W 124.78(17) . . . . ? C8 N2 Cu1 O1W -42.9(2) . . . . ? C12 N2 Cu1 N3 -175.70(13) . . . . ? C8 N2 Cu1 N3 16.62(9) . . . . ? C12 N2 Cu1 N1 2.11(13) . . . . ? C8 N2 Cu1 N1 -165.58(9) . . . . ? C12 N2 Cu1 O2 -75.73(13) . . . . ? C8 N2 Cu1 O2 116.59(9) . . . . ? C2 N1 Cu1 O1W 98.19(10) . . . . ? C3 N1 Cu1 O1W -78.72(11) . . . . ? C2 N1 Cu1 N2 -96.25(10) . . . . ? C3 N1 Cu1 N2 86.84(11) . . . . ? C2 N1 Cu1 O2 2.85(10) . . . . ? C3 N1 Cu1 O2 -174.06(12) . . . . ? C1 O2 Cu1 O1W -95.26(10) . . . . ? C1 O2 Cu1 N3 173.43(10) . . . . ? C1 O2 Cu1 N2 90.72(10) . . . . ? C1 O2 Cu1 N1 -4.31(10) . . . . ? C27 N5 Cu2 O10 179.04(11) . . . . ? C26 N5 Cu2 O10 7.90(10) . . . . ? C27 N5 Cu2 O11 -4.35(10) . . . . ? C26 N5 Cu2 O11 -175.50(11) . . . . ? C27 N5 Cu2 O6 -88.52(11) . . . . ? C26 N5 Cu2 O6 100.33(10) . . . . ? C27 N5 Cu2 O7 89.80(10) . . . . ? C26 N5 Cu2 O7 -81.34(10) . . . . ? C19 N4 Cu2 O10 97.09(11) . . . . ? C20 N4 Cu2 O10 -79.68(10) . . . . ? C19 N4 Cu2 O11 -82.75(11) . . . . ? C20 N4 Cu2 O11 100.48(10) . . . . ? C19 N4 Cu2 O6 2.78(10) . . . . ? C20 N4 Cu2 O6 -173.99(11) . . . . ? C19 N4 Cu2 O7 -174.71(11) . . . . ? C20 N4 Cu2 O7 8.52(10) . . . . ? C25 O10 Cu2 N5 -6.06(10) . . . . ? C25 O10 Cu2 N4 164.96(10) . . . . ? C25 O10 Cu2 O11 -15.49(19) . . . . ? C25 O10 Cu2 O6 -118.34(10) . . . . ? C25 O10 Cu2 O7 88.92(11) . . . . ? C31 O11 Cu2 N5 1.34(9) . . . . ? C31 O11 Cu2 N4 -169.65(9) . . . . ? C31 O11 Cu2 O10 10.80(18) . . . . ? C31 O11 Cu2 O6 114.92(10) . . . . ? C31 O11 Cu2 O7 -92.73(10) . . . . ? C18 O6 Cu2 N5 174.50(10) . . . . ? C18 O6 Cu2 N4 -7.14(10) . . . . ? C18 O6 Cu2 O10 -103.54(10) . . . . ? C18 O6 Cu2 O11 96.72(10) . . . . ? C18 O6 Cu2 O7 -1.93(15) . . . . ? C24 O7 Cu2 N5 166.80(10) . . . . ? C24 O7 Cu2 N4 -11.29(9) . . . . ? C24 O7 Cu2 O10 86.53(10) . . . . ? C24 O7 Cu2 O11 -113.66(10) . . . . ? C24 O7 Cu2 O6 -16.50(15) . . . . ? 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 O1 H1O O3W 0.840(12) 1.614(13) 2.4376(15) 166.3(19) 2_656 O4 H2O O4W 0.832(19) 1.626(19) 2.4515(16) 172(2) 2_666 O1W H3O O12 0.77(2) 1.88(2) 2.6524(15) 179(2) 2_666 O1W H4O O2W 0.81(2) 1.84(2) 2.6393(16) 166.5(19) . O2W H5O O5 0.78(2) 1.93(2) 2.6987(16) 171.9(19) 1_455 O2W H6O O8 0.840(11) 2.118(7) 2.9201(17) 159.6(17) 2_656 O3W H7O O8 0.79(2) 1.79(2) 2.5697(16) 174(2) . O3W H8O O6 0.78(2) 1.82(2) 2.5938(15) 172(2) 1_455 O4W H9O O9 0.76(2) 1.89(2) 2.6309(16) 163(2) 2_755 O4W H10O O7 0.77(2) 1.94(2) 2.7064(16) 173(2) . _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.445 _refine_diff_density_min -0.495 _refine_diff_density_rms 0.064 #===END data_rc08jc2s _database_code_depnum_ccdc_archive 'CCDC 780210' #TrackingRef '- combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C33 H19 Cu2 N5 O12), 11(H2 O)' _chemical_formula_sum 'C66 H60 Cu4 N10 O35' _chemical_formula_weight 1807.40 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_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 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 24.8030(17) _cell_length_b 17.6090(19) _cell_length_c 16.024(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.585(2) _cell_angle_gamma 90.00 _cell_volume 6952.4(15) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 13736 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 25.637 _exptl_crystal_description prism _exptl_crystal_colour blue _exptl_crystal_size_max 0.470 _exptl_crystal_size_mid 0.450 _exptl_crystal_size_min 0.330 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.727 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3688 _exptl_absorpt_coefficient_mu 1.315 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.589 _exptl_absorpt_correction_T_max 0.648 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2003)' _exptl_special_details ; attached with Exxon Paratone N, to a short length of fibre supported on a thin piece of copper wire inserted in a copper mounting pin. The crystal was quenched in a cold nitrogen gas stream from an Oxford Cryosystems Cryostream. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 338 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.15 _diffrn_reflns_number 68268 _diffrn_reflns_av_R_equivalents 0.0470 _diffrn_reflns_av_sigmaI/netI 0.0478 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 28.36 _reflns_number_total 16769 _reflns_number_gt 11598 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker,1995)' _computing_cell_refinement 'SAINT (Bruker,1995)' _computing_data_reduction 'SAINT and XPREP (Bruker 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997), WINGX-32 (Farrugia, 1999)' _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _refine_special_details ; The Water O-bound H atoms were refined with bond length restraints of 0.89(1) \A and the carboxylic acid O-bound H atom with bond length restraint of 0.84(1) \A 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^)+(0.0551P)^2^+3.6668P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 16769 _refine_ls_number_parameters 1114 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0438 _refine_ls_wR_factor_ref 0.1135 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.66355(11) 0.01898(15) 0.57131(16) 0.0184(6) Uani 1 1 d . . . H1 H 0.6951 0.0489 0.5677 0.022 Uiso 1 1 calc R . . C2 C 0.65271(11) -0.00732(16) 0.65022(16) 0.0212(6) Uani 1 1 d . . . H2 H 0.6766 0.0048 0.6990 0.025 Uiso 1 1 calc R . . C3 C 0.60760(11) -0.05045(16) 0.65657(17) 0.0215(6) Uani 1 1 d . . . H3 H 0.5996 -0.0676 0.7100 0.026 Uiso 1 1 calc R . . C4 C 0.57314(11) -0.06931(16) 0.58426(16) 0.0194(6) Uani 1 1 d . . . C5 C 0.58678(10) -0.04070(15) 0.50736(16) 0.0172(5) Uani 1 1 d . . . C6 C 0.55329(10) -0.05765(15) 0.43142(16) 0.0177(6) Uani 1 1 d . . . C7 C 0.50711(11) -0.10365(16) 0.43256(17) 0.0210(6) Uani 1 1 d . . . C8 C 0.49453(11) -0.13263(17) 0.51170(18) 0.0259(7) Uani 1 1 d . . . H8 H 0.4635 -0.1640 0.5133 0.031 Uiso 1 1 calc R . . C9 C 0.52567(11) -0.11638(17) 0.58349(18) 0.0252(6) Uani 1 1 d . . . H9 H 0.5162 -0.1363 0.6349 0.030 Uiso 1 1 calc R . . C10 C 0.47575(11) -0.11729(17) 0.35564(18) 0.0257(6) Uani 1 1 d . . . H10 H 0.4444 -0.1486 0.3530 0.031 Uiso 1 1 calc R . . C11 C 0.49088(12) -0.08495(18) 0.28438(19) 0.0285(7) Uani 1 1 d . . . H11 H 0.4697 -0.0931 0.2319 0.034 Uiso 1 1 calc R . . C12 C 0.53724(11) -0.04012(16) 0.28888(17) 0.0221(6) Uani 1 1 d . . . H12 H 0.5470 -0.0184 0.2385 0.027 Uiso 1 1 calc R . . C13 C 0.69181(11) -0.05121(15) 0.24934(16) 0.0187(6) Uani 1 1 d . . . C14 C 0.65742(10) 0.01146(15) 0.20794(16) 0.0169(5) Uani 1 1 d . . . C15 C 0.60570(10) 0.11792(15) 0.23198(16) 0.0180(6) Uani 1 1 d . . . C16 C 0.59535(11) 0.13160(16) 0.14633(17) 0.0231(6) Uani 1 1 d . . . H16 H 0.5739 0.1739 0.1261 0.028 Uiso 1 1 calc R . . C17 C 0.61675(12) 0.08257(17) 0.09060(18) 0.0256(6) Uani 1 1 d . . . H17 H 0.6095 0.0903 0.0317 0.031 Uiso 1 1 calc R . . C18 C 0.64889(11) 0.02215(16) 0.12213(17) 0.0219(6) Uani 1 1 d . . . H18 H 0.6647 -0.0112 0.0852 0.026 Uiso 1 1 calc R . . C19 C 0.58464(11) 0.16788(15) 0.29903(18) 0.0201(6) Uani 1 1 d . . . C20 C 0.74040(10) 0.12105(15) 0.38234(16) 0.0161(5) Uani 1 1 d . . . C21 C 0.78879(10) 0.16275(15) 0.42678(16) 0.0166(5) Uani 1 1 d . . . C22 C 0.85734(11) 0.24620(15) 0.39673(17) 0.0192(6) Uani 1 1 d . . . C23 C 0.87751(11) 0.25037(16) 0.48074(18) 0.0238(6) Uani 1 1 d . . . H23 H 0.9080 0.2814 0.4985 0.029 Uiso 1 1 calc R . . C24 C 0.85241(11) 0.20856(16) 0.53850(17) 0.0229(6) Uani 1 1 d . . . H24 H 0.8661 0.2103 0.5963 0.027 Uiso 1 1 calc R . . C25 C 0.80692(11) 0.16372(15) 0.51198(16) 0.0184(6) Uani 1 1 d . . . H25 H 0.7892 0.1350 0.5509 0.022 Uiso 1 1 calc R . . C26 C 0.87852(11) 0.28592(17) 0.32220(18) 0.0254(6) Uani 1 1 d . . . C27 C 0.79951(12) 0.10388(17) 0.10587(17) 0.0240(6) Uani 1 1 d . . . C28 C 0.75599(11) 0.16080(16) 0.07961(17) 0.0204(6) Uani 1 1 d . . . C29 C 0.70508(11) 0.25885(16) 0.12678(17) 0.0202(6) Uani 1 1 d . . . C30 C 0.67661(11) 0.26698(17) 0.04836(18) 0.0244(6) Uani 1 1 d . . . H30 H 0.6482 0.3032 0.0392 0.029 Uiso 1 1 calc R . . C31 C 0.68989(12) 0.22177(17) -0.01702(18) 0.0252(6) Uani 1 1 d . . . H31 H 0.6722 0.2288 -0.0723 0.030 Uiso 1 1 calc R . . C32 C 0.72915(12) 0.16628(17) -0.00117(17) 0.0239(6) Uani 1 1 d . . . H32 H 0.7376 0.1328 -0.0443 0.029 Uiso 1 1 calc R . . C33 C 0.69396(11) 0.30603(16) 0.20214(18) 0.0222(6) Uani 1 1 d . . . C34 C 0.82471(11) 0.97717(16) 0.42538(16) 0.0202(6) Uani 1 1 d . . . H34 H 0.7926 0.9493 0.4311 0.024 Uiso 1 1 calc R . . C35 C 0.83570(12) 0.99962(16) 0.34483(17) 0.0231(6) Uani 1 1 d . . . H35 H 0.8109 0.9873 0.2971 0.028 Uiso 1 1 calc R . . C36 C 0.88188(12) 1.03894(17) 0.33503(18) 0.0264(7) Uani 1 1 d . . . H36 H 0.8897 1.0534 0.2806 0.032 Uiso 1 1 calc R . . C37 C 0.91752(11) 1.05783(16) 0.40549(18) 0.0234(6) Uani 1 1 d . . . C38 C 0.90367(10) 1.03460(15) 0.48433(17) 0.0180(6) Uani 1 1 d . . . C39 C 0.93743(11) 1.05390(15) 0.55894(17) 0.0195(6) Uani 1 1 d . . . C40 C 0.98489(11) 1.09689(16) 0.55500(19) 0.0253(6) Uani 1 1 d . . . C41 C 0.99880(12) 1.11888(18) 0.47416(19) 0.0288(7) Uani 1 1 d . . . H41 H 1.0313 1.1467 0.4705 0.035 Uiso 1 1 calc R . . C42 C 0.96700(12) 1.10104(18) 0.4037(2) 0.0304(7) Uani 1 1 d . . . H42 H 0.9772 1.1172 0.3511 0.036 Uiso 1 1 calc R . . C43 C 1.01594(12) 1.11475(18) 0.6311(2) 0.0303(7) Uani 1 1 d . . . H43 H 1.0487 1.1429 0.6315 0.036 Uiso 1 1 calc R . . C44 C 0.99857(13) 1.09121(19) 0.7049(2) 0.0344(8) Uani 1 1 d . . . H44 H 1.0186 1.1041 0.7571 0.041 Uiso 1 1 calc R . . C45 C 0.95145(12) 1.04843(18) 0.70299(19) 0.0288(7) Uani 1 1 d . . . H45 H 0.9404 1.0319 0.7548 0.035 Uiso 1 1 calc R . . C46 C 0.91109(11) 0.83040(16) 0.68877(18) 0.0213(6) Uani 1 1 d . . . C47 C 0.89146(10) 0.87676(15) 0.75948(17) 0.0188(6) Uani 1 1 d . . . C48 C 0.84043(10) 0.98045(15) 0.79308(16) 0.0173(5) Uani 1 1 d . . . C49 C 0.85081(11) 0.96544(16) 0.87798(17) 0.0209(6) Uani 1 1 d . . . H49 H 0.8361 0.9967 0.9180 0.025 Uiso 1 1 calc R . . C50 C 0.88328(11) 0.90360(17) 0.90359(18) 0.0253(6) Uani 1 1 d . . . H50 H 0.8917 0.8926 0.9617 0.030 Uiso 1 1 calc R . . C51 C 0.90332(11) 0.85810(16) 0.84376(17) 0.0221(6) Uani 1 1 d . . . H51 H 0.9248 0.8148 0.8601 0.027 Uiso 1 1 calc R . . C52 C 0.80468(11) 1.04480(16) 0.75827(17) 0.0196(6) Uani 1 1 d . . . C53 C 0.75322(10) 0.87859(15) 0.62269(16) 0.0176(6) Uani 1 1 d . . . C54 C 0.70602(10) 0.83236(15) 0.58193(16) 0.0161(5) Uani 1 1 d . . . C55 C 0.68692(11) 0.82709(15) 0.49765(16) 0.0188(6) Uani 1 1 d . . . H55 H 0.7034 0.8549 0.4565 0.023 Uiso 1 1 calc R . . C56 C 0.64243(11) 0.77941(17) 0.47499(17) 0.0238(6) Uani 1 1 d . . . H56 H 0.6281 0.7748 0.4176 0.029 Uiso 1 1 calc R . . C57 C 0.61914(11) 0.73886(17) 0.53577(17) 0.0231(6) Uani 1 1 d . . . H57 H 0.5895 0.7056 0.5205 0.028 Uiso 1 1 calc R . . C58 C 0.63996(11) 0.74778(15) 0.61910(16) 0.0186(6) Uani 1 1 d . . . C59 C 0.62010(11) 0.71268(17) 0.69657(17) 0.0228(6) Uani 1 1 d . . . C60 C 0.79929(12) 0.70752(16) 0.83287(18) 0.0230(6) Uani 1 1 d . . . C61 C 0.78452(11) 0.76234(16) 0.89929(17) 0.0199(6) Uani 1 1 d . . . C62 C 0.73252(11) 0.86648(16) 0.92711(16) 0.0209(6) Uani 1 1 d . . . C63 C 0.75619(12) 0.86946(18) 1.01005(17) 0.0254(6) Uani 1 1 d . . . H63 H 0.7465 0.9081 1.0470 0.030 Uiso 1 1 calc R . . C64 C 0.79417(12) 0.81468(18) 1.03728(18) 0.0277(7) Uani 1 1 d . . . H64 H 0.8095 0.8136 1.0944 0.033 Uiso 1 1 calc R . . C65 C 0.80970(12) 0.76160(17) 0.98121(18) 0.0264(7) Uani 1 1 d . . . H65 H 0.8371 0.7253 0.9984 0.032 Uiso 1 1 calc R . . C66 C 0.69246(11) 0.92358(17) 0.88781(17) 0.0217(6) Uani 1 1 d . . . N1 N 0.63122(9) 0.00349(12) 0.50139(13) 0.0169(5) Uani 1 1 d . . . N2 N 0.56835(9) -0.02629(13) 0.35986(13) 0.0182(5) Uani 1 1 d . . . N3 N 0.63575(8) 0.05801(12) 0.26104(13) 0.0152(4) Uani 1 1 d . . . N4 N 0.81460(8) 0.20264(12) 0.37273(13) 0.0166(5) Uani 1 1 d . . . N5 N 0.74514(9) 0.20738(13) 0.14151(13) 0.0181(5) Uani 1 1 d . . . N6 N 0.85806(9) 0.99397(12) 0.49342(14) 0.0181(5) Uani 1 1 d . . . N7 N 0.92110(9) 1.02951(13) 0.63267(14) 0.0200(5) Uani 1 1 d . . . N8 N 0.86088(8) 0.93771(13) 0.73514(13) 0.0167(5) Uani 1 1 d . . . N9 N 0.68200(8) 0.79404(12) 0.63961(13) 0.0158(5) Uani 1 1 d . . . N10 N 0.74565(9) 0.81259(13) 0.87370(13) 0.0188(5) Uani 1 1 d . . . O1 O 0.69459(8) -0.06239(11) 0.32472(11) 0.0213(4) Uani 1 1 d . . . O2 O 0.71802(8) -0.08999(11) 0.19719(12) 0.0241(4) Uani 1 1 d D . . H2O H 0.7370(11) -0.1249(13) 0.2212(18) 0.036 Uiso 1 1 d D . . O3 O 0.60092(8) 0.15114(11) 0.37363(11) 0.0218(4) Uani 1 1 d . . . O4 O 0.55298(8) 0.22059(12) 0.27425(13) 0.0303(5) Uani 1 1 d . . . O5 O 0.71117(7) 0.08334(11) 0.42588(11) 0.0194(4) Uani 1 1 d . . . O6 O 0.73404(7) 0.12766(11) 0.30370(11) 0.0208(4) Uani 1 1 d . . . O7 O 0.85465(8) 0.26570(12) 0.25017(12) 0.0255(5) Uani 1 1 d . . . O8 O 0.91577(9) 0.33143(14) 0.33429(14) 0.0424(6) Uani 1 1 d . . . O9 O 0.82350(8) 0.10629(12) 0.17722(12) 0.0301(5) Uani 1 1 d . . . O10 O 0.80770(9) 0.05446(13) 0.04939(13) 0.0341(5) Uani 1 1 d D . . H10O H 0.8287(12) 0.0202(15) 0.070(2) 0.051 Uiso 1 1 d D . . O11 O 0.72941(8) 0.30105(11) 0.26599(12) 0.0225(4) Uani 1 1 d . . . O12 O 0.65283(8) 0.34568(12) 0.19628(13) 0.0310(5) Uani 1 1 d . . . O13 O 0.89490(8) 0.85092(11) 0.61532(12) 0.0234(4) Uani 1 1 d . . . O14 O 0.94133(8) 0.77455(12) 0.70934(13) 0.0293(5) Uani 1 1 d . . . O15 O 0.79845(8) 1.05976(11) 0.68415(11) 0.0228(4) Uani 1 1 d . . . O16 O 0.78172(8) 1.08019(12) 0.81711(12) 0.0272(5) Uani 1 1 d D . . H16O H 0.7648(12) 1.1184(12) 0.796(2) 0.041 Uiso 1 1 d D . . O17 O 0.78142(7) 0.91427(11) 0.57641(11) 0.0201(4) Uani 1 1 d . . . O18 O 0.76007(7) 0.87628(11) 0.70184(11) 0.0216(4) Uani 1 1 d . . . O19 O 0.64222(8) 0.73988(11) 0.76627(11) 0.0241(4) Uani 1 1 d . . . O20 O 0.58584(9) 0.66239(13) 0.68866(13) 0.0379(6) Uani 1 1 d . . . O21 O 0.76710(8) 0.70615(11) 0.76453(12) 0.0246(4) Uani 1 1 d . . . O22 O 0.84121(8) 0.66980(12) 0.84850(13) 0.0316(5) Uani 1 1 d . . . O23 O 0.66977(8) 0.91149(12) 0.81720(12) 0.0270(5) Uani 1 1 d . . . O24 O 0.68604(9) 0.98314(12) 0.93280(13) 0.0284(5) Uani 1 1 d D . . H24O H 0.6674(12) 1.0181(14) 0.9083(19) 0.043 Uiso 1 1 d D . . O1W O 0.51931(9) 0.57793(14) 0.58004(14) 0.0355(5) Uani 1 1 d D A 1 H1W H 0.5246(15) 0.575(2) 0.5261(6) 0.053 Uiso 1 1 d D B 1 H2W H 0.5448(11) 0.6063(18) 0.608(2) 0.053 Uiso 1 1 d D C 1 O2W O 0.63340(9) 0.08621(13) 0.84911(14) 0.0347(5) Uani 1 1 d D D 1 H3W H 0.6363(14) 0.1106(16) 0.8012(11) 0.052 Uiso 1 1 d D E 1 H4W H 0.6113(11) 0.1161(15) 0.8744(17) 0.052 Uiso 1 1 d D F 1 O3W O 0.56497(9) 0.31923(13) 0.41754(15) 0.0346(5) Uani 1 1 d D G 1 H5W H 0.5326(7) 0.3385(19) 0.425(2) 0.052 Uiso 1 1 d D H 1 H6W H 0.5559(14) 0.2868(16) 0.3756(15) 0.052 Uiso 1 1 d D I 1 O4W O 0.88404(9) 0.96951(13) 0.09223(14) 0.0347(5) Uani 1 1 d D J 1 H7W H 0.8796(15) 0.9354(15) 0.1318(17) 0.052 Uiso 1 1 d D K 1 H8W H 0.9094(11) 1.0049(15) 0.104(2) 0.052 Uiso 1 1 d D L 1 O5W O 0.04168(10) 0.80700(16) 0.80736(17) 0.0480(7) Uani 1 1 d D M 1 H9W H 0.0168(13) 0.778(2) 0.778(2) 0.072 Uiso 1 1 d D N 1 H10W H 0.0685(12) 0.7751(19) 0.800(3) 0.072 Uiso 1 1 d D O 1 O6W O 0.88234(9) 0.63824(14) 0.70296(14) 0.0359(5) Uani 1 1 d D P 1 H11W H 0.8647(13) 0.642(2) 0.7481(13) 0.054 Uiso 1 1 d D Q 1 H12W H 0.8988(13) 0.6824(10) 0.696(2) 0.054 Uiso 1 1 d D R 1 O7W O 0.97912(13) 0.41825(19) 0.4421(2) 0.0662(8) Uani 1 1 d D S 1 H13W H 0.9579(17) 0.385(2) 0.412(3) 0.099 Uiso 1 1 d D T 1 H14W H 0.9913(19) 0.4641(12) 0.430(3) 0.099 Uiso 1 1 d D U 1 O8W O 0.02858(11) 0.94183(16) 0.89122(18) 0.0507(7) Uani 1 1 d D V 1 H15W H 0.0387(17) 0.9053(18) 0.858(2) 0.076 Uiso 1 1 d D W 1 H16W H 0.0246(18) 0.928(2) 0.9435(10) 0.076 Uiso 1 1 d D X 1 O9W O 0.55081(11) -0.05277(16) 0.92649(15) 0.0472(6) Uani 1 1 d D Y 1 H17W H 0.5284(13) -0.0153(14) 0.908(2) 0.071 Uiso 1 1 d D Z 1 H18W H 0.5479(16) -0.0843(16) 0.8828(15) 0.071 Uiso 1 1 d D A 1 O10W O 0.45488(10) 0.18027(18) 0.17846(19) 0.0560(8) Uani 1 1 d D B 1 H19W H 0.4291(13) 0.211(2) 0.192(3) 0.084 Uiso 1 1 d D C 1 H20W H 0.4817(13) 0.209(2) 0.203(3) 0.084 Uiso 1 1 d D D 1 O11W O 0.94763(17) 0.7943(2) 0.0381(2) 0.0947(12) Uani 1 1 d D E 1 H21W H 0.9763(16) 0.824(3) 0.051(3) 0.142 Uiso 1 1 d D F 1 H22W H 0.931(2) 0.796(3) 0.085(2) 0.142 Uiso 1 1 d D G 1 Cu1 Cu 0.638762(12) 0.036701(18) 0.384308(19) 0.01516(8) Uani 1 1 d . . . Cu2 Cu 0.785807(13) 0.201565(19) 0.256176(19) 0.01772(8) Uani 1 1 d . . . Cu3 Cu 0.852927(13) 0.963829(19) 0.612856(19) 0.01641(8) Uani 1 1 d . . . Cu4 Cu 0.709389(13) 0.805192(19) 0.755619(19) 0.01816(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0209(14) 0.0181(14) 0.0157(13) 0.0000(10) 0.0008(11) 0.0003(11) C2 0.0279(15) 0.0222(15) 0.0129(13) 0.0013(11) 0.0001(11) 0.0010(12) C3 0.0245(14) 0.0243(15) 0.0166(14) 0.0052(11) 0.0063(11) 0.0047(12) C4 0.0202(14) 0.0217(15) 0.0172(13) 0.0046(11) 0.0061(11) 0.0052(11) C5 0.0172(13) 0.0163(14) 0.0187(13) 0.0014(11) 0.0045(11) 0.0014(11) C6 0.0171(13) 0.0176(14) 0.0189(13) 0.0015(11) 0.0049(11) 0.0028(11) C7 0.0155(13) 0.0220(15) 0.0263(15) 0.0023(12) 0.0060(11) 0.0008(11) C8 0.0185(14) 0.0287(17) 0.0316(16) 0.0063(13) 0.0082(12) -0.0046(12) C9 0.0212(14) 0.0289(16) 0.0274(16) 0.0105(13) 0.0104(12) 0.0014(12) C10 0.0173(14) 0.0288(17) 0.0311(16) -0.0028(13) 0.0033(12) -0.0060(12) C11 0.0219(15) 0.0386(19) 0.0241(15) -0.0061(13) -0.0016(12) -0.0069(13) C12 0.0208(14) 0.0295(16) 0.0159(13) -0.0031(12) 0.0014(11) -0.0040(12) C13 0.0191(13) 0.0202(14) 0.0169(14) 0.0002(11) 0.0022(11) -0.0040(11) C14 0.0150(13) 0.0201(14) 0.0157(13) 0.0008(11) 0.0023(10) -0.0023(11) C15 0.0164(13) 0.0197(14) 0.0177(13) 0.0010(11) 0.0015(11) -0.0031(11) C16 0.0243(15) 0.0224(15) 0.0221(14) 0.0043(12) 0.0002(12) 0.0010(12) C17 0.0274(15) 0.0323(17) 0.0169(14) 0.0037(12) 0.0010(12) -0.0007(13) C18 0.0245(14) 0.0243(15) 0.0171(14) -0.0011(11) 0.0039(11) 0.0005(12) C19 0.0177(13) 0.0167(14) 0.0265(15) -0.0005(11) 0.0044(11) -0.0038(11) C20 0.0165(13) 0.0153(13) 0.0167(13) -0.0006(10) 0.0023(10) 0.0023(10) C21 0.0181(13) 0.0145(13) 0.0177(13) 0.0020(10) 0.0041(10) 0.0021(11) C22 0.0184(13) 0.0175(14) 0.0218(14) -0.0015(11) 0.0026(11) -0.0013(11) C23 0.0205(14) 0.0223(15) 0.0274(15) -0.0040(12) -0.0021(12) -0.0034(12) C24 0.0253(15) 0.0261(16) 0.0158(13) -0.0016(11) -0.0036(11) 0.0028(12) C25 0.0209(14) 0.0198(14) 0.0149(13) 0.0003(11) 0.0043(11) 0.0027(11) C26 0.0216(14) 0.0283(16) 0.0267(16) 0.0014(13) 0.0047(12) -0.0048(13) C27 0.0259(15) 0.0282(16) 0.0181(14) -0.0012(12) 0.0037(12) -0.0032(13) C28 0.0213(14) 0.0211(15) 0.0192(14) 0.0014(11) 0.0041(11) -0.0055(11) C29 0.0200(14) 0.0203(15) 0.0202(14) 0.0028(11) 0.0016(11) -0.0057(11) C30 0.0209(14) 0.0243(16) 0.0270(15) 0.0067(12) -0.0015(12) -0.0024(12) C31 0.0250(15) 0.0285(17) 0.0203(14) 0.0062(12) -0.0046(12) -0.0073(13) C32 0.0302(16) 0.0241(16) 0.0176(14) -0.0018(11) 0.0028(12) -0.0082(13) C33 0.0229(14) 0.0197(15) 0.0247(15) 0.0040(12) 0.0058(12) -0.0030(12) C34 0.0230(14) 0.0205(15) 0.0175(14) -0.0002(11) 0.0044(11) 0.0006(11) C35 0.0277(15) 0.0247(16) 0.0167(14) 0.0022(12) 0.0014(12) 0.0051(12) C36 0.0325(16) 0.0300(17) 0.0182(14) 0.0087(12) 0.0095(12) 0.0111(13) C37 0.0237(14) 0.0217(15) 0.0263(15) 0.0097(12) 0.0085(12) 0.0070(12) C38 0.0189(13) 0.0160(14) 0.0201(14) 0.0023(11) 0.0066(11) 0.0038(11) C39 0.0189(13) 0.0167(14) 0.0242(14) 0.0034(11) 0.0085(11) 0.0034(11) C40 0.0184(14) 0.0216(15) 0.0373(17) 0.0021(13) 0.0088(13) 0.0005(12) C41 0.0212(15) 0.0296(17) 0.0377(18) 0.0103(14) 0.0117(13) -0.0007(13) C42 0.0255(16) 0.0339(18) 0.0342(18) 0.0152(14) 0.0138(14) 0.0042(14) C43 0.0204(15) 0.0301(18) 0.0413(19) -0.0017(14) 0.0080(13) -0.0084(13) C44 0.0273(16) 0.042(2) 0.0333(18) -0.0077(15) 0.0018(14) -0.0140(15) C45 0.0274(16) 0.0345(18) 0.0254(16) -0.0038(13) 0.0065(13) -0.0081(14) C46 0.0177(13) 0.0180(15) 0.0293(16) -0.0037(12) 0.0069(12) -0.0035(11) C47 0.0162(13) 0.0183(14) 0.0218(14) -0.0004(11) 0.0019(11) -0.0028(11) C48 0.0156(13) 0.0184(14) 0.0180(13) -0.0006(11) 0.0023(10) -0.0039(11) C49 0.0222(14) 0.0238(15) 0.0166(13) -0.0011(11) 0.0022(11) -0.0008(12) C50 0.0262(15) 0.0322(17) 0.0168(14) 0.0055(12) -0.0011(11) -0.0006(13) C51 0.0218(14) 0.0215(15) 0.0226(14) 0.0041(12) 0.0006(11) 0.0020(12) C52 0.0196(13) 0.0211(15) 0.0183(14) -0.0006(11) 0.0033(11) -0.0024(11) C53 0.0159(13) 0.0197(14) 0.0169(13) -0.0014(11) 0.0009(10) 0.0008(11) C54 0.0170(13) 0.0177(14) 0.0137(13) -0.0007(10) 0.0021(10) 0.0007(11) C55 0.0203(13) 0.0215(15) 0.0146(13) -0.0014(11) 0.0022(11) 0.0020(11) C56 0.0241(15) 0.0294(16) 0.0167(14) -0.0060(12) -0.0021(11) 0.0016(13) C57 0.0202(14) 0.0262(16) 0.0221(15) -0.0041(12) -0.0009(11) -0.0050(12) C58 0.0185(13) 0.0188(14) 0.0184(13) -0.0018(11) 0.0021(11) -0.0008(11) C59 0.0213(14) 0.0279(16) 0.0189(14) 0.0003(12) 0.0017(11) -0.0036(12) C60 0.0256(15) 0.0196(15) 0.0237(15) 0.0051(12) 0.0018(12) -0.0049(12) C61 0.0175(13) 0.0209(15) 0.0212(14) 0.0039(11) 0.0022(11) -0.0052(11) C62 0.0210(14) 0.0278(16) 0.0138(13) 0.0010(11) 0.0022(11) -0.0049(12) C63 0.0301(16) 0.0316(17) 0.0140(13) -0.0022(12) 0.0012(12) -0.0038(13) C64 0.0267(16) 0.0352(18) 0.0204(15) -0.0001(13) -0.0012(12) -0.0040(14) C65 0.0229(15) 0.0286(17) 0.0264(16) 0.0084(13) -0.0032(12) -0.0047(13) C66 0.0205(14) 0.0285(16) 0.0167(14) 0.0006(12) 0.0045(11) -0.0021(12) N1 0.0184(11) 0.0165(12) 0.0162(11) 0.0006(9) 0.0041(9) -0.0006(9) N2 0.0196(11) 0.0194(12) 0.0161(11) -0.0020(9) 0.0041(9) -0.0022(9) N3 0.0122(10) 0.0191(12) 0.0143(11) 0.0010(9) 0.0019(8) -0.0029(9) N4 0.0142(11) 0.0186(12) 0.0168(11) -0.0004(9) 0.0010(9) -0.0006(9) N5 0.0169(11) 0.0217(12) 0.0154(11) 0.0029(9) 0.0011(9) -0.0048(9) N6 0.0206(12) 0.0158(12) 0.0189(11) 0.0008(9) 0.0071(9) 0.0021(9) N7 0.0192(11) 0.0223(13) 0.0193(12) -0.0012(9) 0.0052(9) -0.0025(10) N8 0.0143(11) 0.0193(12) 0.0167(11) -0.0006(9) 0.0024(9) -0.0024(9) N9 0.0158(11) 0.0176(12) 0.0141(11) -0.0003(9) 0.0019(9) -0.0010(9) N10 0.0174(11) 0.0235(13) 0.0153(11) 0.0020(9) 0.0016(9) -0.0052(10) O1 0.0272(11) 0.0226(10) 0.0142(10) 0.0010(8) 0.0023(8) 0.0027(8) O2 0.0302(11) 0.0249(11) 0.0178(10) -0.0001(8) 0.0054(8) 0.0114(9) O3 0.0245(10) 0.0216(11) 0.0195(10) -0.0021(8) 0.0040(8) 0.0014(8) O4 0.0313(12) 0.0264(12) 0.0324(12) -0.0002(9) 0.0004(9) 0.0101(10) O5 0.0198(9) 0.0230(10) 0.0156(9) 0.0015(8) 0.0026(8) -0.0046(8) O6 0.0210(10) 0.0259(11) 0.0148(9) 0.0015(8) -0.0009(8) -0.0095(8) O7 0.0245(10) 0.0317(12) 0.0204(10) 0.0046(9) 0.0023(8) -0.0078(9) O8 0.0411(14) 0.0515(16) 0.0342(13) 0.0040(11) 0.0027(11) -0.0291(12) O9 0.0337(12) 0.0365(13) 0.0189(11) -0.0034(9) -0.0019(9) 0.0094(10) O10 0.0380(13) 0.0374(14) 0.0258(12) -0.0099(10) -0.0012(10) 0.0119(10) O11 0.0228(10) 0.0219(11) 0.0223(10) 0.0000(8) 0.0001(8) -0.0025(8) O12 0.0271(11) 0.0313(12) 0.0342(12) 0.0002(10) 0.0016(9) 0.0089(10) O13 0.0245(10) 0.0265(11) 0.0199(10) -0.0027(8) 0.0058(8) -0.0001(9) O14 0.0284(11) 0.0246(11) 0.0347(12) -0.0028(9) 0.0020(9) 0.0067(9) O15 0.0287(11) 0.0246(11) 0.0150(10) 0.0036(8) 0.0020(8) 0.0026(9) O16 0.0334(12) 0.0290(12) 0.0201(10) 0.0032(9) 0.0067(9) 0.0149(9) O17 0.0186(9) 0.0254(11) 0.0166(9) 0.0018(8) 0.0028(8) -0.0052(8) O18 0.0209(10) 0.0299(11) 0.0137(9) 0.0013(8) 0.0008(8) -0.0078(8) O19 0.0235(10) 0.0322(12) 0.0169(10) 0.0007(8) 0.0029(8) -0.0086(9) O20 0.0391(13) 0.0467(15) 0.0276(12) 0.0002(10) 0.0031(10) -0.0267(11) O21 0.0260(11) 0.0240(11) 0.0229(10) 0.0002(8) -0.0006(8) -0.0037(9) O22 0.0319(12) 0.0301(12) 0.0317(12) 0.0008(9) -0.0011(10) 0.0092(10) O23 0.0314(11) 0.0326(12) 0.0154(10) -0.0038(8) -0.0046(8) 0.0034(9) O24 0.0308(12) 0.0330(13) 0.0208(11) -0.0062(9) -0.0001(9) 0.0077(10) O1W 0.0336(13) 0.0406(14) 0.0319(13) -0.0086(11) 0.0027(10) -0.0079(11) O2W 0.0411(13) 0.0365(14) 0.0277(12) 0.0054(10) 0.0085(10) 0.0084(11) O3W 0.0302(12) 0.0347(13) 0.0389(14) -0.0132(10) 0.0049(11) -0.0033(10) O4W 0.0372(13) 0.0331(14) 0.0338(13) 0.0003(10) 0.0038(11) 0.0046(10) O5W 0.0376(15) 0.0600(19) 0.0457(16) -0.0159(13) 0.0021(12) 0.0032(13) O6W 0.0369(14) 0.0364(14) 0.0343(13) -0.0031(11) 0.0037(10) 0.0006(11) O7W 0.068(2) 0.068(2) 0.061(2) -0.0101(17) 0.0047(16) -0.0182(17) O8W 0.0486(16) 0.0445(17) 0.0583(18) -0.0010(14) 0.0039(14) -0.0009(13) O9W 0.0547(17) 0.0483(17) 0.0392(15) 0.0026(12) 0.0086(12) 0.0089(13) O10W 0.0345(15) 0.071(2) 0.0609(18) -0.0251(15) -0.0017(13) 0.0137(14) O11W 0.114(3) 0.081(3) 0.093(3) 0.040(2) 0.027(2) 0.020(2) Cu1 0.01644(16) 0.01828(17) 0.01086(15) 0.00049(12) 0.00195(12) -0.00312(13) Cu2 0.01769(17) 0.02155(18) 0.01362(16) 0.00163(13) 0.00051(13) -0.00385(13) Cu3 0.01733(16) 0.01932(18) 0.01303(16) 0.00043(13) 0.00367(12) -0.00331(13) Cu4 0.01848(17) 0.02328(19) 0.01245(16) 0.00052(13) 0.00065(13) -0.00551(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.329(3) . ? C1 C2 1.401(4) . ? C1 H1 0.9500 . ? C2 C3 1.366(4) . ? C2 H2 0.9500 . ? C3 C4 1.399(4) . ? C3 H3 0.9500 . ? C4 C5 1.408(4) . ? C4 C9 1.439(4) . ? C5 N1 1.362(3) . ? C5 C6 1.424(4) . ? C6 N2 1.363(3) . ? C6 C7 1.405(4) . ? C7 C10 1.401(4) . ? C7 C8 1.434(4) . ? C8 C9 1.341(4) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 C11 1.366(4) . ? C10 H10 0.9500 . ? C11 C12 1.390(4) . ? C11 H11 0.9500 . ? C12 N2 1.322(3) . ? C12 H12 0.9500 . ? C13 O1 1.218(3) . ? C13 O2 1.308(3) . ? C13 C14 1.502(4) . ? C14 N3 1.338(3) . ? C14 C18 1.380(4) . ? C15 N3 1.344(3) . ? C15 C16 1.388(4) . ? C15 C19 1.527(4) . ? C16 C17 1.390(4) . ? C16 H16 0.9500 . ? C17 C18 1.389(4) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 O4 1.251(3) . ? C19 O3 1.252(3) . ? C20 O5 1.253(3) . ? C20 O6 1.257(3) . ? C20 C21 1.514(4) . ? C21 N4 1.334(3) . ? C21 C25 1.388(4) . ? C22 N4 1.329(3) . ? C22 C23 1.383(4) . ? C22 C26 1.528(4) . ? C23 C24 1.385(4) . ? C23 H23 0.9500 . ? C24 C25 1.403(4) . ? C24 H24 0.9500 . ? C25 H25 0.9500 . ? C26 O8 1.222(3) . ? C26 O7 1.286(3) . ? C27 O9 1.228(3) . ? C27 O10 1.288(3) . ? C27 C28 1.498(4) . ? C28 N5 1.338(3) . ? C28 C32 1.389(4) . ? C29 N5 1.346(3) . ? C29 C30 1.376(4) . ? C29 C33 1.517(4) . ? C30 C31 1.385(4) . ? C30 H30 0.9500 . ? C31 C32 1.382(4) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 O12 1.231(3) . ? C33 O11 1.273(3) . ? C34 N6 1.324(3) . ? C34 C35 1.406(4) . ? C34 H34 0.9500 . ? C35 C36 1.363(4) . ? C35 H35 0.9500 . ? C36 C37 1.392(4) . ? C36 H36 0.9500 . ? C37 C38 1.407(4) . ? C37 C42 1.447(4) . ? C38 N6 1.361(3) . ? C38 C39 1.420(4) . ? C39 N7 1.362(3) . ? C39 C40 1.407(4) . ? C40 C43 1.402(4) . ? C40 C41 1.432(4) . ? C41 C42 1.339(4) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C43 C44 1.369(4) . ? C43 H43 0.9500 . ? C44 C45 1.388(4) . ? C44 H44 0.9500 . ? C45 N7 1.324(4) . ? C45 H45 0.9500 . ? C46 O13 1.253(3) . ? C46 O14 1.258(3) . ? C46 C47 1.521(4) . ? C47 N8 1.346(3) . ? C47 C51 1.388(4) . ? C48 N8 1.339(3) . ? C48 C49 1.381(4) . ? C48 C52 1.506(4) . ? C49 C50 1.388(4) . ? C49 H49 0.9500 . ? C50 C51 1.385(4) . ? C50 H50 0.9500 . ? C51 H51 0.9500 . ? C52 O15 1.209(3) . ? C52 O16 1.313(3) . ? C53 O17 1.246(3) . ? C53 O18 1.261(3) . ? C53 C54 1.511(4) . ? C54 N9 1.338(3) . ? C54 C55 1.382(3) . ? C55 C56 1.401(4) . ? C55 H55 0.9500 . ? C56 C57 1.386(4) . ? C56 H56 0.9500 . ? C57 C58 1.384(4) . ? C57 H57 0.9500 . ? C58 N9 1.334(3) . ? C58 C59 1.518(4) . ? C59 O20 1.224(3) . ? C59 O19 1.280(3) . ? C60 O22 1.235(3) . ? C60 O21 1.279(3) . ? C60 C61 1.513(4) . ? C61 N10 1.338(3) . ? C61 C65 1.388(4) . ? C62 N10 1.343(3) . ? C62 C63 1.391(4) . ? C62 C66 1.500(4) . ? C63 C64 1.384(4) . ? C63 H63 0.9500 . ? C64 C65 1.382(4) . ? C64 H64 0.9500 . ? C65 H65 0.9500 . ? C66 O23 1.223(3) . ? C66 O24 1.293(3) . ? N1 Cu1 1.994(2) . ? N2 Cu1 2.068(2) . ? N3 Cu1 2.003(2) . ? N4 Cu2 1.922(2) . ? N5 Cu2 1.995(2) . ? N6 Cu3 2.004(2) . ? N7 Cu3 2.043(2) . ? N8 Cu3 2.000(2) . ? N9 Cu4 1.915(2) . ? N10 Cu4 2.004(2) . ? O2 H2O 0.84(3) . ? O3 Cu1 2.2213(19) . ? O5 Cu1 2.0173(18) . ? O6 Cu2 2.0362(18) . ? O7 Cu2 2.0587(19) . ? O9 Cu2 2.358(2) . ? O10 H10O 0.84(3) . ? O11 Cu2 2.2584(19) . ? O13 Cu3 2.242(2) . ? O16 H16O 0.84(3) . ? O17 Cu3 2.0026(18) . ? O18 Cu4 2.0342(18) . ? O19 Cu4 2.0475(18) . ? O21 Cu4 2.250(2) . ? O23 Cu4 2.380(2) . ? O24 H24O 0.84(3) . ? O1W H1W 0.891(14) . ? O1W H2W 0.89(3) . ? O2W H3W 0.89(3) . ? O2W H4W 0.89(3) . ? O3W H5W 0.89(3) . ? O3W H6W 0.89(3) . ? O4W H7W 0.89(3) . ? O4W H8W 0.89(3) . ? O5W H9W 0.89(3) . ? O5W H10W 0.89(3) . ? O6W H11W 0.89(3) . ? O6W H12W 0.89(3) . ? O7W H13W 0.89(3) . ? O7W H14W 0.89(3) . ? O8W H15W 0.89(3) . ? O8W H16W 0.89(3) . ? O9W H17W 0.89(3) . ? O9W H18W 0.89(3) . ? O10W H19W 0.89(4) . ? O10W H20W 0.89(4) . ? O11W H21W 0.89(5) . ? O11W H22W 0.90(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.2(3) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C2 C3 C4 119.9(2) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C3 C4 C5 117.1(2) . . ? C3 C4 C9 124.4(2) . . ? C5 C4 C9 118.5(2) . . ? N1 C5 C4 122.9(2) . . ? N1 C5 C6 117.2(2) . . ? C4 C5 C6 119.9(2) . . ? N2 C6 C7 123.2(2) . . ? N2 C6 C5 116.4(2) . . ? C7 C6 C5 120.4(2) . . ? C10 C7 C6 117.3(2) . . ? C10 C7 C8 124.2(3) . . ? C6 C7 C8 118.5(3) . . ? C9 C8 C7 121.4(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C4 121.4(3) . . ? C8 C9 H9 119.3 . . ? C4 C9 H9 119.3 . . ? C11 C10 C7 119.1(3) . . ? C11 C10 H10 120.5 . . ? C7 C10 H10 120.5 . . ? C10 C11 C12 119.9(3) . . ? C10 C11 H11 120.1 . . ? C12 C11 H11 120.1 . . ? N2 C12 C11 123.2(3) . . ? N2 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? O1 C13 O2 125.0(3) . . ? O1 C13 C14 121.4(2) . . ? O2 C13 C14 113.6(2) . . ? N3 C14 C18 121.6(2) . . ? N3 C14 C13 114.7(2) . . ? C18 C14 C13 123.7(2) . . ? N3 C15 C16 120.7(2) . . ? N3 C15 C19 115.4(2) . . ? C16 C15 C19 123.8(2) . . ? C15 C16 C17 119.1(3) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C18 C17 C16 119.2(3) . . ? C18 C17 H17 120.4 . . ? C16 C17 H17 120.4 . . ? C14 C18 C17 118.9(3) . . ? C14 C18 H18 120.6 . . ? C17 C18 H18 120.6 . . ? O4 C19 O3 126.9(3) . . ? O4 C19 C15 117.2(2) . . ? O3 C19 C15 115.9(2) . . ? O5 C20 O6 126.4(2) . . ? O5 C20 C21 118.3(2) . . ? O6 C20 C21 115.3(2) . . ? N4 C21 C25 120.4(2) . . ? N4 C21 C20 111.3(2) . . ? C25 C21 C20 128.2(2) . . ? N4 C22 C23 120.0(2) . . ? N4 C22 C26 111.8(2) . . ? C23 C22 C26 128.2(2) . . ? C22 C23 C24 118.8(3) . . ? C22 C23 H23 120.6 . . ? C24 C23 H23 120.6 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C21 C25 C24 117.6(2) . . ? C21 C25 H25 121.2 . . ? C24 C25 H25 121.2 . . ? O8 C26 O7 125.9(3) . . ? O8 C26 C22 119.9(3) . . ? O7 C26 C22 114.3(2) . . ? O9 C27 O10 125.4(3) . . ? O9 C27 C28 119.7(3) . . ? O10 C27 C28 114.9(2) . . ? N5 C28 C32 122.2(3) . . ? N5 C28 C27 113.7(2) . . ? C32 C28 C27 124.1(3) . . ? N5 C29 C30 121.4(3) . . ? N5 C29 C33 115.3(2) . . ? C30 C29 C33 123.3(3) . . ? C29 C30 C31 119.3(3) . . ? C29 C30 H30 120.4 . . ? C31 C30 H30 120.4 . . ? C32 C31 C30 119.4(3) . . ? C32 C31 H31 120.3 . . ? C30 C31 H31 120.3 . . ? C31 C32 C28 118.2(3) . . ? C31 C32 H32 120.9 . . ? C28 C32 H32 120.9 . . ? O12 C33 O11 126.2(3) . . ? O12 C33 C29 118.3(3) . . ? O11 C33 C29 115.5(2) . . ? N6 C34 C35 121.6(3) . . ? N6 C34 H34 119.2 . . ? C35 C34 H34 119.2 . . ? C36 C35 C34 120.2(3) . . ? C36 C35 H35 119.9 . . ? C34 C35 H35 119.9 . . ? C35 C36 C37 119.5(3) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C36 C37 C38 117.5(3) . . ? C36 C37 C42 124.8(3) . . ? C38 C37 C42 117.8(3) . . ? N6 C38 C37 122.7(3) . . ? N6 C38 C39 116.9(2) . . ? C37 C38 C39 120.3(2) . . ? N7 C39 C40 122.8(3) . . ? N7 C39 C38 116.7(2) . . ? C40 C39 C38 120.4(2) . . ? C43 C40 C39 117.4(3) . . ? C43 C40 C41 124.1(3) . . ? C39 C40 C41 118.4(3) . . ? C42 C41 C40 121.3(3) . . ? C42 C41 H41 119.3 . . ? C40 C41 H41 119.3 . . ? C41 C42 C37 121.7(3) . . ? C41 C42 H42 119.2 . . ? C37 C42 H42 119.2 . . ? C44 C43 C40 119.2(3) . . ? C44 C43 H43 120.4 . . ? C40 C43 H43 120.4 . . ? C43 C44 C45 119.5(3) . . ? C43 C44 H44 120.2 . . ? C45 C44 H44 120.2 . . ? N7 C45 C44 123.4(3) . . ? N7 C45 H45 118.3 . . ? C44 C45 H45 118.3 . . ? O13 C46 O14 126.1(3) . . ? O13 C46 C47 116.7(2) . . ? O14 C46 C47 117.2(3) . . ? N8 C47 C51 121.3(2) . . ? N8 C47 C46 115.5(2) . . ? C51 C47 C46 123.2(3) . . ? N8 C48 C49 122.2(3) . . ? N8 C48 C52 114.8(2) . . ? C49 C48 C52 123.0(2) . . ? C48 C49 C50 118.5(3) . . ? C48 C49 H49 120.7 . . ? C50 C49 H49 120.7 . . ? C51 C50 C49 119.4(3) . . ? C51 C50 H50 120.3 . . ? C49 C50 H50 120.3 . . ? C50 C51 C47 118.9(3) . . ? C50 C51 H51 120.5 . . ? C47 C51 H51 120.5 . . ? O15 C52 O16 125.8(3) . . ? O15 C52 C48 122.1(2) . . ? O16 C52 C48 112.1(2) . . ? O17 C53 O18 126.5(2) . . ? O17 C53 C54 118.3(2) . . ? O18 C53 C54 115.2(2) . . ? N9 C54 C55 120.7(2) . . ? N9 C54 C53 110.9(2) . . ? C55 C54 C53 128.3(2) . . ? C54 C55 C56 117.7(2) . . ? C54 C55 H55 121.1 . . ? C56 C55 H55 121.1 . . ? C57 C56 C55 120.4(3) . . ? C57 C56 H56 119.8 . . ? C55 C56 H56 119.8 . . ? C58 C57 C56 118.7(3) . . ? C58 C57 H57 120.7 . . ? C56 C57 H57 120.7 . . ? N9 C58 C57 120.1(2) . . ? N9 C58 C59 111.4(2) . . ? C57 C58 C59 128.5(2) . . ? O20 C59 O19 125.8(3) . . ? O20 C59 C58 119.8(3) . . ? O19 C59 C58 114.5(2) . . ? O22 C60 O21 126.3(3) . . ? O22 C60 C61 117.8(3) . . ? O21 C60 C61 115.9(2) . . ? N10 C61 C65 121.8(3) . . ? N10 C61 C60 115.5(2) . . ? C65 C61 C60 122.7(3) . . ? N10 C62 C63 121.9(3) . . ? N10 C62 C66 113.8(2) . . ? C63 C62 C66 124.2(3) . . ? C64 C63 C62 118.2(3) . . ? C64 C63 H63 120.9 . . ? C62 C63 H63 120.9 . . ? C65 C64 C63 119.8(3) . . ? C65 C64 H64 120.1 . . ? C63 C64 H64 120.1 . . ? C64 C65 C61 118.7(3) . . ? C64 C65 H65 120.7 . . ? C61 C65 H65 120.7 . . ? O23 C66 O24 125.7(3) . . ? O23 C66 C62 118.9(3) . . ? O24 C66 C62 115.3(2) . . ? C1 N1 C5 118.2(2) . . ? C1 N1 Cu1 128.34(18) . . ? C5 N1 Cu1 113.44(17) . . ? C12 N2 C6 117.4(2) . . ? C12 N2 Cu1 131.21(19) . . ? C6 N2 Cu1 111.39(17) . . ? C14 N3 C15 120.5(2) . . ? C14 N3 Cu1 122.69(18) . . ? C15 N3 Cu1 116.44(17) . . ? C22 N4 C21 122.8(2) . . ? C22 N4 Cu2 118.83(18) . . ? C21 N4 Cu2 118.25(18) . . ? C28 N5 C29 119.3(2) . . ? C28 N5 Cu2 121.88(19) . . ? C29 N5 Cu2 118.78(18) . . ? C34 N6 C38 118.6(2) . . ? C34 N6 Cu3 128.68(18) . . ? C38 N6 Cu3 112.72(17) . . ? C45 N7 C39 117.5(2) . . ? C45 N7 Cu3 130.88(19) . . ? C39 N7 Cu3 111.53(18) . . ? C48 N8 C47 119.5(2) . . ? C48 N8 Cu3 123.18(18) . . ? C47 N8 Cu3 117.14(17) . . ? C58 N9 C54 122.3(2) . . ? C58 N9 Cu4 118.82(17) . . ? C54 N9 Cu4 118.84(18) . . ? C61 N10 C62 119.4(2) . . ? C61 N10 Cu4 118.43(18) . . ? C62 N10 Cu4 122.16(19) . . ? C13 O2 H2O 113(2) . . ? C19 O3 Cu1 111.98(17) . . ? C20 O5 Cu1 125.60(17) . . ? C20 O6 Cu2 114.96(16) . . ? C26 O7 Cu2 114.14(17) . . ? C27 O9 Cu2 110.17(18) . . ? C27 O10 H10O 111(3) . . ? C33 O11 Cu2 111.94(17) . . ? C46 O13 Cu3 111.76(17) . . ? C52 O16 H16O 109(2) . . ? C53 O17 Cu3 125.80(17) . . ? C53 O18 Cu4 115.31(17) . . ? C59 O19 Cu4 114.14(17) . . ? C60 O21 Cu4 111.70(18) . . ? C66 O23 Cu4 110.63(18) . . ? C66 O24 H24O 116(2) . . ? H1W O1W H2W 111(3) . . ? H3W O2W H4W 103(3) . . ? H5W O3W H6W 101(3) . . ? H7W O4W H8W 118(3) . . ? H9W O5W H10W 93(4) . . ? H11W O6W H12W 108(3) . . ? H13W O7W H14W 132(5) . . ? H15W O8W H16W 116(4) . . ? H17W O9W H18W 102(3) . . ? H19W O10W H20W 94(4) . . ? H21W O11W H22W 102(3) . . ? N1 Cu1 N3 170.21(9) . . ? N1 Cu1 O5 89.12(8) . . ? N3 Cu1 O5 100.40(8) . . ? N1 Cu1 N2 81.53(9) . . ? N3 Cu1 N2 88.76(8) . . ? O5 Cu1 N2 168.94(8) . . ? N1 Cu1 O3 104.72(8) . . ? N3 Cu1 O3 77.68(8) . . ? O5 Cu1 O3 90.48(7) . . ? N2 Cu1 O3 97.57(8) . . ? N4 Cu2 N5 170.78(9) . . ? N4 Cu2 O6 79.79(8) . . ? N5 Cu2 O6 95.93(8) . . ? N4 Cu2 O7 79.76(8) . . ? N5 Cu2 O7 105.27(8) . . ? O6 Cu2 O7 158.44(7) . . ? N4 Cu2 O11 95.10(8) . . ? N5 Cu2 O11 76.85(8) . . ? O6 Cu2 O11 92.72(7) . . ? O7 Cu2 O11 95.82(8) . . ? N4 Cu2 O9 113.73(8) . . ? N5 Cu2 O9 74.45(8) . . ? O6 Cu2 O9 92.97(8) . . ? O7 Cu2 O9 89.04(8) . . ? O11 Cu2 O9 151.17(7) . . ? N8 Cu3 O17 99.79(8) . . ? N8 Cu3 N6 170.54(9) . . ? O17 Cu3 N6 89.32(8) . . ? N8 Cu3 N7 89.49(9) . . ? O17 Cu3 N7 168.95(9) . . ? N6 Cu3 N7 81.75(9) . . ? N8 Cu3 O13 77.61(8) . . ? O17 Cu3 O13 90.72(7) . . ? N6 Cu3 O13 99.87(8) . . ? N7 Cu3 O13 97.18(8) . . ? N9 Cu4 N10 173.84(9) . . ? N9 Cu4 O18 79.60(8) . . ? N10 Cu4 O18 97.34(8) . . ? N9 Cu4 O19 79.74(8) . . ? N10 Cu4 O19 103.84(8) . . ? O18 Cu4 O19 158.30(7) . . ? N9 Cu4 O21 97.72(8) . . ? N10 Cu4 O21 77.12(8) . . ? O18 Cu4 O21 94.84(7) . . ? O19 Cu4 O21 94.42(8) . . ? N9 Cu4 O23 111.45(8) . . ? N10 Cu4 O23 73.70(8) . . ? O18 Cu4 O23 89.79(8) . . ? O19 Cu4 O23 91.64(8) . . ? O21 Cu4 O23 150.81(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 0.1(4) . . . . ? C1 C2 C3 C4 1.2(4) . . . . ? C2 C3 C4 C5 -1.3(4) . . . . ? C2 C3 C4 C9 177.9(3) . . . . ? C3 C4 C5 N1 0.0(4) . . . . ? C9 C4 C5 N1 -179.2(2) . . . . ? C3 C4 C5 C6 -179.8(2) . . . . ? C9 C4 C5 C6 1.0(4) . . . . ? N1 C5 C6 N2 -1.5(4) . . . . ? C4 C5 C6 N2 178.3(2) . . . . ? N1 C5 C6 C7 179.2(2) . . . . ? C4 C5 C6 C7 -0.9(4) . . . . ? N2 C6 C7 C10 0.2(4) . . . . ? C5 C6 C7 C10 179.3(3) . . . . ? N2 C6 C7 C8 -178.9(3) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C10 C7 C8 C9 -178.7(3) . . . . ? C6 C7 C8 C9 0.3(4) . . . . ? C7 C8 C9 C4 -0.2(5) . . . . ? C3 C4 C9 C8 -179.6(3) . . . . ? C5 C4 C9 C8 -0.5(4) . . . . ? C6 C7 C10 C11 -0.8(4) . . . . ? C8 C7 C10 C11 178.2(3) . . . . ? C7 C10 C11 C12 0.9(5) . . . . ? C10 C11 C12 N2 -0.2(5) . . . . ? O1 C13 C14 N3 7.2(4) . . . . ? O2 C13 C14 N3 -171.8(2) . . . . ? O1 C13 C14 C18 -173.8(3) . . . . ? O2 C13 C14 C18 7.2(4) . . . . ? N3 C15 C16 C17 -0.3(4) . . . . ? C19 C15 C16 C17 179.7(2) . . . . ? C15 C16 C17 C18 -1.4(4) . . . . ? N3 C14 C18 C17 -0.4(4) . . . . ? C13 C14 C18 C17 -179.3(3) . . . . ? C16 C17 C18 C14 1.7(4) . . . . ? N3 C15 C19 O4 -174.4(2) . . . . ? C16 C15 C19 O4 5.5(4) . . . . ? N3 C15 C19 O3 5.2(3) . . . . ? C16 C15 C19 O3 -174.8(2) . . . . ? O5 C20 C21 N4 -177.5(2) . . . . ? O6 C20 C21 N4 3.1(3) . . . . ? O5 C20 C21 C25 1.8(4) . . . . ? O6 C20 C21 C25 -177.5(3) . . . . ? N4 C22 C23 C24 0.0(4) . . . . ? C26 C22 C23 C24 -179.1(3) . . . . ? C22 C23 C24 C25 -0.9(4) . . . . ? N4 C21 C25 C24 0.8(4) . . . . ? C20 C21 C25 C24 -178.5(2) . . . . ? C23 C24 C25 C21 0.4(4) . . . . ? N4 C22 C26 O8 175.8(3) . . . . ? C23 C22 C26 O8 -5.0(5) . . . . ? N4 C22 C26 O7 -5.5(4) . . . . ? C23 C22 C26 O7 173.7(3) . . . . ? O9 C27 C28 N5 -4.2(4) . . . . ? O10 C27 C28 N5 174.7(2) . . . . ? O9 C27 C28 C32 175.3(3) . . . . ? O10 C27 C28 C32 -5.9(4) . . . . ? N5 C29 C30 C31 -0.7(4) . . . . ? C33 C29 C30 C31 179.5(2) . . . . ? C29 C30 C31 C32 3.9(4) . . . . ? C30 C31 C32 C28 -3.4(4) . . . . ? N5 C28 C32 C31 -0.3(4) . . . . ? C27 C28 C32 C31 -179.7(3) . . . . ? N5 C29 C33 O12 -169.1(2) . . . . ? C30 C29 C33 O12 10.7(4) . . . . ? N5 C29 C33 O11 11.8(3) . . . . ? C30 C29 C33 O11 -168.4(3) . . . . ? N6 C34 C35 C36 0.7(4) . . . . ? C34 C35 C36 C37 -1.1(4) . . . . ? C35 C36 C37 C38 0.2(4) . . . . ? C35 C36 C37 C42 -178.3(3) . . . . ? C36 C37 C38 N6 1.2(4) . . . . ? C42 C37 C38 N6 179.8(2) . . . . ? C36 C37 C38 C39 -178.2(3) . . . . ? C42 C37 C38 C39 0.4(4) . . . . ? N6 C38 C39 N7 0.4(4) . . . . ? C37 C38 C39 N7 179.8(2) . . . . ? N6 C38 C39 C40 -179.0(2) . . . . ? C37 C38 C39 C40 0.4(4) . . . . ? N7 C39 C40 C43 -0.1(4) . . . . ? C38 C39 C40 C43 179.2(3) . . . . ? N7 C39 C40 C41 179.2(3) . . . . ? C38 C39 C40 C41 -1.5(4) . . . . ? C43 C40 C41 C42 -179.0(3) . . . . ? C39 C40 C41 C42 1.8(4) . . . . ? C40 C41 C42 C37 -0.9(5) . . . . ? C36 C37 C42 C41 178.3(3) . . . . ? C38 C37 C42 C41 -0.2(4) . . . . ? C39 C40 C43 C44 -1.2(4) . . . . ? C41 C40 C43 C44 179.6(3) . . . . ? C40 C43 C44 C45 1.7(5) . . . . ? C43 C44 C45 N7 -1.1(5) . . . . ? O13 C46 C47 N8 -3.4(4) . . . . ? O14 C46 C47 N8 177.6(2) . . . . ? O13 C46 C47 C51 176.0(2) . . . . ? O14 C46 C47 C51 -3.0(4) . . . . ? N8 C48 C49 C50 -0.4(4) . . . . ? C52 C48 C49 C50 178.5(2) . . . . ? C48 C49 C50 C51 -1.3(4) . . . . ? C49 C50 C51 C47 1.6(4) . . . . ? N8 C47 C51 C50 -0.2(4) . . . . ? C46 C47 C51 C50 -179.6(3) . . . . ? N8 C48 C52 O15 -5.3(4) . . . . ? C49 C48 C52 O15 175.8(3) . . . . ? N8 C48 C52 O16 174.0(2) . . . . ? C49 C48 C52 O16 -5.0(4) . . . . ? O17 C53 C54 N9 176.2(2) . . . . ? O18 C53 C54 N9 -3.3(3) . . . . ? O17 C53 C54 C55 -4.2(4) . . . . ? O18 C53 C54 C55 176.2(3) . . . . ? N9 C54 C55 C56 -1.1(4) . . . . ? C53 C54 C55 C56 179.4(3) . . . . ? C54 C55 C56 C57 -0.5(4) . . . . ? C55 C56 C57 C58 1.4(4) . . . . ? C56 C57 C58 N9 -0.7(4) . . . . ? C56 C57 C58 C59 177.1(3) . . . . ? N9 C58 C59 O20 -171.8(3) . . . . ? C57 C58 C59 O20 10.3(5) . . . . ? N9 C58 C59 O19 7.9(3) . . . . ? C57 C58 C59 O19 -170.1(3) . . . . ? O22 C60 C61 N10 166.8(2) . . . . ? O21 C60 C61 N10 -11.8(3) . . . . ? O22 C60 C61 C65 -12.6(4) . . . . ? O21 C60 C61 C65 168.8(2) . . . . ? N10 C62 C63 C64 -0.2(4) . . . . ? C66 C62 C63 C64 -177.5(3) . . . . ? C62 C63 C64 C65 3.5(4) . . . . ? C63 C64 C65 C61 -3.2(4) . . . . ? N10 C61 C65 C64 -0.4(4) . . . . ? C60 C61 C65 C64 178.9(3) . . . . ? N10 C62 C66 O23 10.1(4) . . . . ? C63 C62 C66 O23 -172.4(3) . . . . ? N10 C62 C66 O24 -168.5(2) . . . . ? C63 C62 C66 O24 8.9(4) . . . . ? C2 C1 N1 C5 -1.3(4) . . . . ? C2 C1 N1 Cu1 178.9(2) . . . . ? C4 C5 N1 C1 1.2(4) . . . . ? C6 C5 N1 C1 -178.9(2) . . . . ? C4 C5 N1 Cu1 -178.9(2) . . . . ? C6 C5 N1 Cu1 1.0(3) . . . . ? C11 C12 N2 C6 -0.5(4) . . . . ? C11 C12 N2 Cu1 179.5(2) . . . . ? C7 C6 N2 C12 0.5(4) . . . . ? C5 C6 N2 C12 -178.7(2) . . . . ? C7 C6 N2 Cu1 -179.5(2) . . . . ? C5 C6 N2 Cu1 1.3(3) . . . . ? C18 C14 N3 C15 -1.4(4) . . . . ? C13 C14 N3 C15 177.7(2) . . . . ? C18 C14 N3 Cu1 171.57(19) . . . . ? C13 C14 N3 Cu1 -9.4(3) . . . . ? C16 C15 N3 C14 1.7(4) . . . . ? C19 C15 N3 C14 -178.3(2) . . . . ? C16 C15 N3 Cu1 -171.7(2) . . . . ? C19 C15 N3 Cu1 8.3(3) . . . . ? C23 C22 N4 C21 1.3(4) . . . . ? C26 C22 N4 C21 -179.4(2) . . . . ? C23 C22 N4 Cu2 177.4(2) . . . . ? C26 C22 N4 Cu2 -3.3(3) . . . . ? C25 C21 N4 C22 -1.7(4) . . . . ? C20 C21 N4 C22 177.7(2) . . . . ? C25 C21 N4 Cu2 -177.86(19) . . . . ? C20 C21 N4 Cu2 1.5(3) . . . . ? C32 C28 N5 C29 3.5(4) . . . . ? C27 C28 N5 C29 -177.0(2) . . . . ? C32 C28 N5 Cu2 -177.7(2) . . . . ? C27 C28 N5 Cu2 1.8(3) . . . . ? C30 C29 N5 C28 -3.0(4) . . . . ? C33 C29 N5 C28 176.8(2) . . . . ? C30 C29 N5 Cu2 178.2(2) . . . . ? C33 C29 N5 Cu2 -2.0(3) . . . . ? C35 C34 N6 C38 0.6(4) . . . . ? C35 C34 N6 Cu3 -176.6(2) . . . . ? C37 C38 N6 C34 -1.6(4) . . . . ? C39 C38 N6 C34 177.8(2) . . . . ? C37 C38 N6 Cu3 176.0(2) . . . . ? C39 C38 N6 Cu3 -4.6(3) . . . . ? C44 C45 N7 C39 -0.2(4) . . . . ? C44 C45 N7 Cu3 176.8(2) . . . . ? C40 C39 N7 C45 0.8(4) . . . . ? C38 C39 N7 C45 -178.5(3) . . . . ? C40 C39 N7 Cu3 -176.7(2) . . . . ? C38 C39 N7 Cu3 4.0(3) . . . . ? C49 C48 N8 C47 1.8(4) . . . . ? C52 C48 N8 C47 -177.2(2) . . . . ? C49 C48 N8 Cu3 -173.60(19) . . . . ? C52 C48 N8 Cu3 7.4(3) . . . . ? C51 C47 N8 C48 -1.5(4) . . . . ? C46 C47 N8 C48 177.9(2) . . . . ? C51 C47 N8 Cu3 174.2(2) . . . . ? C46 C47 N8 Cu3 -6.4(3) . . . . ? C57 C58 N9 C54 -0.9(4) . . . . ? C59 C58 N9 C54 -179.1(2) . . . . ? C57 C58 N9 Cu4 179.7(2) . . . . ? C59 C58 N9 Cu4 1.6(3) . . . . ? C55 C54 N9 C58 1.9(4) . . . . ? C53 C54 N9 C58 -178.5(2) . . . . ? C55 C54 N9 Cu4 -178.75(19) . . . . ? C53 C54 N9 Cu4 0.8(3) . . . . ? C65 C61 N10 C62 3.7(4) . . . . ? C60 C61 N10 C62 -175.7(2) . . . . ? C65 C61 N10 Cu4 -176.9(2) . . . . ? C60 C61 N10 Cu4 3.7(3) . . . . ? C63 C62 N10 C61 -3.4(4) . . . . ? C66 C62 N10 C61 174.2(2) . . . . ? C63 C62 N10 Cu4 177.3(2) . . . . ? C66 C62 N10 Cu4 -5.2(3) . . . . ? O4 C19 O3 Cu1 165.2(2) . . . . ? C15 C19 O3 Cu1 -14.3(3) . . . . ? O6 C20 O5 Cu1 -10.8(4) . . . . ? C21 C20 O5 Cu1 169.95(16) . . . . ? O5 C20 O6 Cu2 174.7(2) . . . . ? C21 C20 O6 Cu2 -6.0(3) . . . . ? O8 C26 O7 Cu2 -170.4(3) . . . . ? C22 C26 O7 Cu2 10.9(3) . . . . ? O10 C27 O9 Cu2 -174.7(2) . . . . ? C28 C27 O9 Cu2 4.0(3) . . . . ? O12 C33 O11 Cu2 166.7(2) . . . . ? C29 C33 O11 Cu2 -14.3(3) . . . . ? O14 C46 O13 Cu3 -171.0(2) . . . . ? C47 C46 O13 Cu3 10.1(3) . . . . ? O18 C53 O17 Cu3 11.1(4) . . . . ? C54 C53 O17 Cu3 -168.40(17) . . . . ? O17 C53 O18 Cu4 -175.4(2) . . . . ? C54 C53 O18 Cu4 4.1(3) . . . . ? O20 C59 O19 Cu4 166.7(3) . . . . ? C58 C59 O19 Cu4 -12.9(3) . . . . ? O22 C60 O21 Cu4 -165.6(2) . . . . ? C61 C60 O21 Cu4 12.9(3) . . . . ? O24 C66 O23 Cu4 169.3(2) . . . . ? C62 C66 O23 Cu4 -9.2(3) . . . . ? C1 N1 Cu1 O5 5.6(2) . . . . ? C5 N1 Cu1 O5 -174.27(18) . . . . ? C1 N1 Cu1 N2 179.6(2) . . . . ? C5 N1 Cu1 N2 -0.20(18) . . . . ? C1 N1 Cu1 O3 -84.7(2) . . . . ? C5 N1 Cu1 O3 95.46(18) . . . . ? C14 N3 Cu1 O5 86.9(2) . . . . ? C15 N3 Cu1 O5 -99.93(19) . . . . ? C14 N3 Cu1 N2 -86.9(2) . . . . ? C15 N3 Cu1 N2 86.30(19) . . . . ? C14 N3 Cu1 O3 175.1(2) . . . . ? C15 N3 Cu1 O3 -11.72(18) . . . . ? C20 O5 Cu1 N1 -175.9(2) . . . . ? C20 O5 Cu1 N3 6.4(2) . . . . ? C20 O5 Cu1 N2 151.9(4) . . . . ? C20 O5 Cu1 O3 -71.2(2) . . . . ? C12 N2 Cu1 N1 179.4(3) . . . . ? C6 N2 Cu1 N1 -0.59(18) . . . . ? C12 N2 Cu1 N3 -1.8(3) . . . . ? C6 N2 Cu1 N3 178.16(18) . . . . ? C12 N2 Cu1 O5 -148.0(4) . . . . ? C6 N2 Cu1 O5 32.0(5) . . . . ? C12 N2 Cu1 O3 75.6(3) . . . . ? C6 N2 Cu1 O3 -104.44(18) . . . . ? C19 O3 Cu1 N1 -155.67(18) . . . . ? C19 O3 Cu1 N3 14.57(17) . . . . ? C19 O3 Cu1 O5 115.11(18) . . . . ? C19 O3 Cu1 N2 -72.48(18) . . . . ? C22 N4 Cu2 O6 -179.8(2) . . . . ? C21 N4 Cu2 O6 -3.56(19) . . . . ? C22 N4 Cu2 O7 7.04(19) . . . . ? C21 N4 Cu2 O7 -176.7(2) . . . . ? C22 N4 Cu2 O11 -88.0(2) . . . . ? C21 N4 Cu2 O11 88.3(2) . . . . ? C22 N4 Cu2 O9 91.4(2) . . . . ? C21 N4 Cu2 O9 -92.3(2) . . . . ? C28 N5 Cu2 O6 -91.3(2) . . . . ? C29 N5 Cu2 O6 87.48(19) . . . . ? C28 N5 Cu2 O7 84.7(2) . . . . ? C29 N5 Cu2 O7 -96.47(19) . . . . ? C28 N5 Cu2 O11 177.2(2) . . . . ? C29 N5 Cu2 O11 -3.94(18) . . . . ? C28 N5 Cu2 O9 0.09(19) . . . . ? C29 N5 Cu2 O9 178.9(2) . . . . ? C20 O6 Cu2 N4 5.36(18) . . . . ? C20 O6 Cu2 N5 -166.39(19) . . . . ? C20 O6 Cu2 O7 24.0(3) . . . . ? C20 O6 Cu2 O11 -89.33(18) . . . . ? C20 O6 Cu2 O9 118.95(18) . . . . ? C26 O7 Cu2 N4 -10.1(2) . . . . ? C26 O7 Cu2 N5 162.0(2) . . . . ? C26 O7 Cu2 O6 -28.8(3) . . . . ? C26 O7 Cu2 O11 84.1(2) . . . . ? C26 O7 Cu2 O9 -124.4(2) . . . . ? C33 O11 Cu2 N4 -165.02(18) . . . . ? C33 O11 Cu2 N5 10.42(17) . . . . ? C33 O11 Cu2 O6 -85.04(18) . . . . ? C33 O11 Cu2 O7 114.78(18) . . . . ? C33 O11 Cu2 O9 16.1(3) . . . . ? C27 O9 Cu2 N4 173.17(19) . . . . ? C27 O9 Cu2 N5 -2.32(19) . . . . ? C27 O9 Cu2 O6 93.0(2) . . . . ? C27 O9 Cu2 O7 -108.5(2) . . . . ? C27 O9 Cu2 O11 -8.1(3) . . . . ? C48 N8 Cu3 O17 -87.3(2) . . . . ? C47 N8 Cu3 O17 97.22(19) . . . . ? C48 N8 Cu3 N7 86.7(2) . . . . ? C47 N8 Cu3 N7 -88.82(19) . . . . ? C48 N8 Cu3 O13 -175.9(2) . . . . ? C47 N8 Cu3 O13 8.64(18) . . . . ? C53 O17 Cu3 N8 0.1(2) . . . . ? C53 O17 Cu3 N6 177.5(2) . . . . ? C53 O17 Cu3 N7 -146.6(4) . . . . ? C53 O17 Cu3 O13 77.6(2) . . . . ? C34 N6 Cu3 O17 -4.0(2) . . . . ? C38 N6 Cu3 O17 178.64(18) . . . . ? C34 N6 Cu3 N7 -177.5(2) . . . . ? C38 N6 Cu3 N7 5.16(18) . . . . ? C34 N6 Cu3 O13 86.6(2) . . . . ? C38 N6 Cu3 O13 -90.75(18) . . . . ? C45 N7 Cu3 N8 -5.6(3) . . . . ? C39 N7 Cu3 N8 171.51(19) . . . . ? C45 N7 Cu3 O17 141.7(4) . . . . ? C39 N7 Cu3 O17 -41.3(5) . . . . ? C45 N7 Cu3 N6 178.0(3) . . . . ? C39 N7 Cu3 N6 -4.93(18) . . . . ? C45 N7 Cu3 O13 -83.0(3) . . . . ? C39 N7 Cu3 O13 94.06(18) . . . . ? C46 O13 Cu3 N8 -10.38(18) . . . . ? C46 O13 Cu3 O17 -110.25(18) . . . . ? C46 O13 Cu3 N6 160.32(18) . . . . ? C46 O13 Cu3 N7 77.50(18) . . . . ? C58 N9 Cu4 O18 -179.7(2) . . . . ? C54 N9 Cu4 O18 0.93(19) . . . . ? C58 N9 Cu4 O19 -6.36(19) . . . . ? C54 N9 Cu4 O19 174.3(2) . . . . ? C58 N9 Cu4 O21 86.8(2) . . . . ? C54 N9 Cu4 O21 -92.6(2) . . . . ? C58 N9 Cu4 O23 -94.1(2) . . . . ? C54 N9 Cu4 O23 86.6(2) . . . . ? C61 N10 Cu4 O18 -91.13(19) . . . . ? C62 N10 Cu4 O18 88.2(2) . . . . ? C61 N10 Cu4 O19 93.62(19) . . . . ? C62 N10 Cu4 O19 -87.0(2) . . . . ? C61 N10 Cu4 O21 2.18(18) . . . . ? C62 N10 Cu4 O21 -178.5(2) . . . . ? C61 N10 Cu4 O23 -178.7(2) . . . . ? C62 N10 Cu4 O23 0.60(19) . . . . ? C53 O18 Cu4 N9 -2.91(19) . . . . ? C53 O18 Cu4 N10 171.68(19) . . . . ? C53 O18 Cu4 O19 -20.9(3) . . . . ? C53 O18 Cu4 O21 94.08(19) . . . . ? C53 O18 Cu4 O23 -114.78(19) . . . . ? C59 O19 Cu4 N9 10.9(2) . . . . ? C59 O19 Cu4 N10 -164.0(2) . . . . ? C59 O19 Cu4 O18 28.8(3) . . . . ? C59 O19 Cu4 O21 -86.2(2) . . . . ? C59 O19 Cu4 O23 122.4(2) . . . . ? C60 O21 Cu4 N9 167.94(18) . . . . ? C60 O21 Cu4 N10 -8.64(18) . . . . ? C60 O21 Cu4 O18 87.81(18) . . . . ? C60 O21 Cu4 O19 -111.84(18) . . . . ? C60 O21 Cu4 O23 -10.5(3) . . . . ? C66 O23 Cu4 N9 -171.48(18) . . . . ? C66 O23 Cu4 N10 4.97(19) . . . . ? C66 O23 Cu4 O18 -92.75(19) . . . . ? C66 O23 Cu4 O19 108.91(19) . . . . ? C66 O23 Cu4 O21 6.8(3) . . . . ? 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 O2 H2O O21 0.84(3) 1.72(2) 2.555(3) 171(3) 4_565 O10 H10O O4W 0.84(3) 1.64(3) 2.449(3) 160(4) 1_545 O16 H16O O11 0.84(3) 1.71(2) 2.546(3) 173(4) 4_576 O24 H24O O2W 0.84(3) 1.69(3) 2.529(3) 173(4) 1_565 O1W H1W O9W 0.891(14) 1.834(11) 2.702(3) 164(4) 4_565 O1W H2W O20 0.89(3) 1.84(3) 2.703(3) 165(4) . O2W H3W O12 0.89(3) 1.94(2) 2.818(3) 171(3) 4_566 O2W H4W O3W 0.89(3) 1.81(3) 2.699(3) 175(3) 4_566 O3W H5W O1W 0.89(3) 1.951(17) 2.769(3) 152(3) 3_666 O3W H6W O4 0.89(3) 1.99(3) 2.867(3) 166(3) . O4W H7W O6W 0.89(3) 1.72(3) 2.601(3) 169(4) 4_575 O4W H8W O8W 0.89(3) 1.80(3) 2.660(4) 163(4) 3_676 O5W H9W O14 0.89(3) 2.06(2) 2.845(3) 146(4) 1_455 O5W H10W O7 0.89(3) 2.266(17) 3.105(3) 157(4) 3_666 O6W H11W O22 0.89(3) 1.838(10) 2.708(3) 165(4) . O6W H12W O14 0.89(3) 1.93(2) 2.807(3) 167(4) . O7W H13W O8 0.89(3) 1.80(4) 2.678(4) 169(5) . O7W H14W O8W 0.89(3) 2.03(3) 2.910(4) 170(5) 4_675 O8W H15W O5W 0.89(3) 1.916(16) 2.766(4) 159(4) . O8W H16W O7W 0.89(3) 1.853(10) 2.731(4) 168(4) 2_656 O9W H17W O1W 0.89(3) 2.05(3) 2.879(3) 156(3) 2_646 O9W H18W O10W 0.89(3) 1.95(3) 2.799(4) 159(3) 3_656 O10W H19W O19 0.89(3) 2.14(4) 3.008(3) 165(4) 3_666 O10W H20W O4 0.89(3) 2.00(2) 2.815(3) 151(4) . O11W H21W O7W 0.89(3) 1.99(5) 2.835(5) 159(6) 2_755 O11W H22W O14 0.89(3) 2.34(5) 3.020(4) 133(5) 4_575 O11W H22W O6W 0.89(3) 2.63(3) 3.463(4) 156(5) 4_575 _diffrn_measured_fraction_theta_max 0.964 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.866 _refine_diff_density_min -0.989 _refine_diff_density_rms 0.095 #===END data_rc07pj2 _database_code_depnum_ccdc_archive 'CCDC 780211' #TrackingRef '- combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C21 H18 Cu2 O17), 8(H2 O)' _chemical_formula_sum 'C42 H52 Cu4 O42' _chemical_formula_weight 1483.00 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' 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.458(2) _cell_length_b 15.890(2) _cell_length_c 11.4300(10) _cell_angle_alpha 90.00 _cell_angle_beta 99.318(4) _cell_angle_gamma 90.00 _cell_volume 2770.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9168 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 30.00 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1512 _exptl_absorpt_coefficient_mu 1.632 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7590 _exptl_absorpt_correction_T_max 0.95274 _exptl_absorpt_process_details 'APEX (Bruker-Nonius, 2003)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. The Water O-bound H atoms were refined with bond length restraints of 0.87(1) \A and the carboxylic acid O-bound H atom with bond length restraint of 0.84(1) \A O11 and O11A are disordered over three sites and were modelled with identical thermal parameters. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 39772 _diffrn_reflns_av_R_equivalents 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 30.02 _reflns_number_total 4043 _reflns_number_gt 3720 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _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^)+(0.0307P)^2^+6.5393P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4043 _refine_ls_number_parameters 234 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0281 _refine_ls_wR_factor_ref 0.0749 _refine_ls_wR_factor_gt 0.0725 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.30916(10) 0.23718(10) 0.30618(13) 0.0131(3) Uani 1 1 d . . . C2 C 0.34416(10) 0.23552(11) 0.19141(14) 0.0139(3) Uani 1 1 d . . . C3 C 0.33016(11) 0.16985(11) 0.00619(14) 0.0148(3) Uani 1 1 d . . . C4 C 0.38413(12) 0.22420(12) -0.03324(15) 0.0188(3) Uani 1 1 d . . . H4 H 0.3936 0.2198 -0.1131 0.023 Uiso 1 1 calc R . . C5 C 0.43048(12) 0.29207(13) 0.04343(16) 0.0209(3) Uani 1 1 d . . . H5A H 0.4192 0.3473 0.0037 0.025 Uiso 1 1 calc R . . H5B H 0.4945 0.2817 0.0560 0.025 Uiso 1 1 calc R . . C6 C 0.39858(11) 0.29342(12) 0.16077(15) 0.0171(3) Uani 1 1 d . . . H6 H 0.4180 0.3373 0.2152 0.021 Uiso 1 1 calc R . . C7 C 0.28045(11) 0.10314(11) -0.06666(14) 0.0153(3) Uani 1 1 d . . . C8 C 0.37021(10) 0.15669(10) 0.60574(13) 0.0116(3) Uani 1 1 d . . . C9 C 0.43820(10) 0.10146(10) 0.67600(13) 0.0126(3) Uani 1 1 d . . . C10 C 0.43606(12) 0.01821(11) 0.67108(17) 0.0205(3) Uani 1 1 d . . . H10 H 0.3922 -0.0081 0.6152 0.025 Uiso 1 1 calc R . . C11 C 0.5000 -0.03628(17) 0.7500 0.0327(7) Uani 1 2 d S . . H11A H 0.4682 -0.0728 0.7989 0.039 Uiso 0.50 1 calc PR . . H11B H 0.5318 -0.0728 0.7011 0.039 Uiso 0.50 1 calc PR . . O1 O 0.25434(8) 0.18099(8) 0.32273(11) 0.0171(2) Uani 1 1 d . . . O2 O 0.33680(8) 0.29507(8) 0.37746(10) 0.0170(2) Uani 1 1 d . . . O3 O 0.31128(9) 0.16848(8) 0.12077(10) 0.0172(2) Uani 1 1 d . . . O4 O 0.22958(9) 0.05636(8) -0.02663(11) 0.0194(2) Uani 1 1 d . . . O5 O 0.29635(9) 0.09999(9) -0.17568(11) 0.0225(3) Uani 1 1 d D . . H1O H 0.2656(14) 0.0606(11) -0.209(2) 0.027 Uiso 1 1 d D . . O6 O 0.30313(7) 0.12036(8) 0.55062(11) 0.0157(2) Uani 1 1 d . . . O7 O 0.38470(8) 0.23472(8) 0.60903(11) 0.0159(2) Uani 1 1 d . . . O8 O 0.5000 0.14811(10) 0.7500 0.0144(3) Uani 1 2 d S . . O9 O 0.11714(8) 0.07755(8) 0.42600(12) 0.0208(3) Uani 1 1 d D . . H2O H 0.0905(15) 0.0746(17) 0.4873(14) 0.031 Uiso 1 1 d D . . H3O H 0.1482(14) 0.0320(9) 0.425(2) 0.031 Uiso 1 1 d D . . O10 O 0.21409(9) 0.02506(9) 0.21087(11) 0.0215(3) Uani 1 1 d D . . H4O H 0.2217(17) 0.0282(17) 0.1372(7) 0.032 Uiso 1 1 d D . . H5O H 0.2268(17) 0.0736(8) 0.244(2) 0.032 Uiso 1 1 d D . . O11 O 0.0000 0.1433(3) 0.2500 0.0265(8) Uiso 0.50 2 d SPD A 1 H6O H 0.037(3) 0.1235(11) 0.207(5) 0.040 Uiso 0.25 1 d PD B 1 H7O H 0.0000 0.1981(3) 0.2500 0.040 Uiso 0.50 2 d SPD C 1 O11A O 0.0261(4) 0.1459(4) 0.2202(6) 0.0265(8) Uiso 0.25 1 d PD . 2 H6O1 H -0.016(5) 0.115(6) 0.183(9) 0.040 Uiso 0.25 1 d PD D 2 H7O1 H 0.0000 0.1874(6) 0.2500 0.040 Uiso 0.50 2 d SPD E 2 O12 O 0.0417(2) 0.0324(2) 0.6249(4) 0.0429(9) Uani 0.50 1 d PD . . H8O H 0.013(4) -0.010(3) 0.591(6) 0.064 Uiso 0.50 1 d PD . . H9O H 0.085(3) 0.015(4) 0.677(5) 0.064 Uiso 0.50 1 d PD . . Cu1 Cu 0.201724(12) 0.183680(12) 0.469601(15) 0.01009(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0123(7) 0.0170(7) 0.0095(6) 0.0009(5) 0.0007(5) 0.0031(5) C2 0.0142(7) 0.0174(7) 0.0099(6) -0.0016(5) 0.0017(5) 0.0013(6) C3 0.0175(7) 0.0182(8) 0.0091(6) -0.0010(5) 0.0029(5) 0.0028(6) C4 0.0193(8) 0.0249(9) 0.0135(7) -0.0018(6) 0.0068(6) -0.0003(7) C5 0.0205(8) 0.0268(9) 0.0171(8) -0.0019(7) 0.0087(6) -0.0057(7) C6 0.0155(7) 0.0224(8) 0.0137(7) -0.0028(6) 0.0031(6) -0.0018(6) C7 0.0190(7) 0.0170(7) 0.0097(6) 0.0004(5) 0.0021(5) 0.0037(6) C8 0.0100(6) 0.0160(7) 0.0086(6) -0.0004(5) 0.0008(5) 0.0002(5) C9 0.0098(6) 0.0163(7) 0.0106(6) -0.0005(5) -0.0022(5) -0.0009(5) C10 0.0163(7) 0.0165(8) 0.0249(8) -0.0022(6) -0.0084(6) 0.0002(6) C11 0.0284(14) 0.0136(12) 0.0472(18) 0.000 -0.0212(13) 0.000 O1 0.0202(6) 0.0211(6) 0.0107(5) -0.0017(4) 0.0049(4) -0.0037(5) O2 0.0179(6) 0.0227(6) 0.0106(5) -0.0036(4) 0.0031(4) -0.0030(5) O3 0.0256(6) 0.0178(6) 0.0092(5) -0.0021(4) 0.0062(4) -0.0047(5) O4 0.0270(6) 0.0184(6) 0.0125(5) -0.0002(4) 0.0028(5) -0.0041(5) O5 0.0299(7) 0.0275(7) 0.0117(6) -0.0053(5) 0.0084(5) -0.0058(6) O6 0.0120(5) 0.0168(6) 0.0159(5) -0.0004(4) -0.0052(4) 0.0002(4) O7 0.0133(5) 0.0148(5) 0.0173(5) 0.0022(4) -0.0044(4) -0.0001(4) O8 0.0121(7) 0.0135(8) 0.0145(7) 0.000 -0.0070(6) 0.000 O9 0.0156(6) 0.0175(6) 0.0275(7) 0.0029(5) -0.0014(5) -0.0028(5) O10 0.0313(7) 0.0219(6) 0.0120(6) 0.0008(5) 0.0055(5) -0.0015(5) O12 0.0173(14) 0.0333(18) 0.081(3) 0.0268(18) 0.0151(16) 0.0029(12) Cu1 0.00916(9) 0.01319(10) 0.00718(9) -0.00032(6) -0.00091(6) -0.00060(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.257(2) . ? C1 O1 1.266(2) . ? C1 C2 1.498(2) . ? C2 C6 1.331(2) . ? C2 O3 1.383(2) . ? C3 C4 1.329(2) . ? C3 O3 1.3873(19) . ? C3 C7 1.483(2) . ? C4 C5 1.497(3) . ? C4 H4 0.9500 . ? C5 C6 1.502(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6 0.9500 . ? C7 O4 1.223(2) . ? C7 O5 1.3095(19) . ? C8 O7 1.259(2) . ? C8 O6 1.2625(19) . ? C8 C9 1.499(2) . ? C9 C10 1.324(2) . ? C9 O8 1.3842(17) . ? C10 C11 1.501(2) . ? C10 H10 0.9500 . ? C11 C10 1.501(2) 2_656 ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? O1 Cu1 1.9808(12) . ? O2 Cu1 1.9651(12) 7_556 ? O5 H1O 0.839(19) . ? O6 Cu1 1.9639(12) . ? O7 Cu1 1.9711(12) 7_556 ? O8 C9 1.3842(17) 2_656 ? O9 Cu1 2.1426(13) . ? O9 H2O 0.870(17) . ? O9 H3O 0.870(11) . ? O10 H4O 0.870(11) . ? O10 H5O 0.868(16) . ? O11 H6O 0.870(1) . ? O11 H7O 0.870(1) . ? O11 H6O1 0.89(7) . ? O11 H7O1 0.700(11) . ? O11A O11A 1.138(13) 2 ? O11A H6O 0.431(13) . ? O11A H7O 1.005(9) . ? O11A H6O1 0.870(1) . ? O11A H7O1 0.870(1) . ? O12 H8O 0.8698(10) . ? O12 H9O 0.8698(10) . ? Cu1 O2 1.9651(12) 7_556 ? Cu1 O7 1.9711(12) 7_556 ? Cu1 Cu1 2.6109(4) 7_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 125.79(15) . . ? O2 C1 C2 116.58(14) . . ? O1 C1 C2 117.63(14) . . ? C6 C2 O3 124.54(15) . . ? C6 C2 C1 123.47(15) . . ? O3 C2 C1 111.97(14) . . ? C4 C3 O3 124.73(15) . . ? C4 C3 C7 124.79(15) . . ? O3 C3 C7 110.48(14) . . ? C3 C4 C5 122.47(15) . . ? C3 C4 H4 118.8 . . ? C5 C4 H4 118.8 . . ? C4 C5 C6 109.73(15) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C2 C6 C5 122.54(16) . . ? C2 C6 H6 118.7 . . ? C5 C6 H6 118.7 . . ? O4 C7 O5 124.31(16) . . ? O4 C7 C3 122.01(14) . . ? O5 C7 C3 113.68(15) . . ? O7 C8 O6 126.36(15) . . ? O7 C8 C9 117.05(13) . . ? O6 C8 C9 116.59(14) . . ? C10 C9 O8 124.82(15) . . ? C10 C9 C8 123.49(14) . . ? O8 C9 C8 111.62(14) . . ? C9 C10 C11 122.78(17) . . ? C9 C10 H10 118.6 . . ? C11 C10 H10 118.6 . . ? C10 C11 C10 109.5(2) 2_656 . ? C10 C11 H11A 109.8 2_656 . ? C10 C11 H11A 109.8 . . ? C10 C11 H11B 109.8 2_656 . ? C10 C11 H11B 109.8 . . ? H11A C11 H11B 108.2 . . ? C1 O1 Cu1 119.21(11) . . ? C1 O2 Cu1 125.60(11) . 7_556 ? C2 O3 C3 115.19(13) . . ? C7 O5 H1O 106.4(18) . . ? C8 O6 Cu1 121.97(11) . . ? C8 O7 Cu1 122.00(10) . 7_556 ? C9 O8 C9 115.24(18) . 2_656 ? Cu1 O9 H2O 101.9(18) . . ? Cu1 O9 H3O 110.0(17) . . ? H2O O9 H3O 108(2) . . ? H4O O10 H5O 109(2) . . ? H6O O11 H7O 111.2(12) . . ? H6O O11 H6O1 56(7) . . ? H7O O11 H6O1 120(7) . . ? H6O O11 H7O1 111.2(12) . . ? H6O1 O11 H7O1 120(7) . . ? O11A O11A H6O 124(2) 2 . ? O11A O11A H7O 55.5(4) 2 . ? H6O O11A H7O 180(9) . . ? O11A O11A H6O1 76(8) 2 . ? H6O O11A H6O1 71(10) . . ? H7O O11A H6O1 109(8) . . ? O11A O11A H7O1 49.2(6) 2 . ? H6O O11A H7O1 173(3) . . ? H6O1 O11A H7O1 105(8) . . ? H8O O12 H9O 111(7) . . ? O6 Cu1 O2 90.13(5) . 7_556 ? O6 Cu1 O7 169.22(5) . 7_556 ? O2 Cu1 O7 90.68(5) 7_556 7_556 ? O6 Cu1 O1 89.01(5) . . ? O2 Cu1 O1 169.35(5) 7_556 . ? O7 Cu1 O1 88.21(5) 7_556 . ? O6 Cu1 O9 96.71(5) . . ? O2 Cu1 O9 94.63(5) 7_556 . ? O7 Cu1 O9 93.94(5) 7_556 . ? O1 Cu1 O9 96.02(5) . . ? O6 Cu1 Cu1 84.83(4) . 7_556 ? O2 Cu1 Cu1 82.36(4) 7_556 7_556 ? O7 Cu1 Cu1 84.63(4) 7_556 7_556 ? O1 Cu1 Cu1 86.99(4) . 7_556 ? O9 Cu1 Cu1 176.64(4) . 7_556 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C6 -3.1(2) . . . . ? O1 C1 C2 C6 176.48(16) . . . . ? O2 C1 C2 O3 178.61(14) . . . . ? O1 C1 C2 O3 -1.8(2) . . . . ? O3 C3 C4 C5 -0.8(3) . . . . ? C7 C3 C4 C5 178.02(16) . . . . ? C3 C4 C5 C6 -6.2(3) . . . . ? O3 C2 C6 C5 0.2(3) . . . . ? C1 C2 C6 C5 -177.90(16) . . . . ? C4 C5 C6 C2 6.5(2) . . . . ? C4 C3 C7 O4 -177.77(17) . . . . ? O3 C3 C7 O4 1.2(2) . . . . ? C4 C3 C7 O5 2.1(3) . . . . ? O3 C3 C7 O5 -178.93(14) . . . . ? O7 C8 C9 C10 -172.80(17) . . . . ? O6 C8 C9 C10 8.4(2) . . . . ? O7 C8 C9 O8 10.24(19) . . . . ? O6 C8 C9 O8 -168.54(12) . . . . ? O8 C9 C10 C11 2.2(3) . . . . ? C8 C9 C10 C11 -174.32(13) . . . . ? C9 C10 C11 C10 -1.07(13) . . . 2_656 ? O2 C1 O1 Cu1 2.5(2) . . . . ? C2 C1 O1 Cu1 -177.05(10) . . . . ? O1 C1 O2 Cu1 -2.8(2) . . . 7_556 ? C2 C1 O2 Cu1 176.76(10) . . . 7_556 ? C6 C2 O3 C3 -7.6(2) . . . . ? C1 C2 O3 C3 170.70(13) . . . . ? C4 C3 O3 C2 7.9(2) . . . . ? C7 C3 O3 C2 -171.06(14) . . . . ? O7 C8 O6 Cu1 -5.9(2) . . . . ? C9 C8 O6 Cu1 172.75(10) . . . . ? O6 C8 O7 Cu1 2.8(2) . . . 7_556 ? C9 C8 O7 Cu1 -175.80(10) . . . 7_556 ? C10 C9 O8 C9 -1.14(14) . . . 2_656 ? C8 C9 O8 C9 175.77(15) . . . 2_656 ? C8 O6 Cu1 O2 -77.69(12) . . . 7_556 ? C8 O6 Cu1 O7 16.6(3) . . . 7_556 ? C8 O6 Cu1 O1 91.70(12) . . . . ? C8 O6 Cu1 O9 -172.36(12) . . . . ? C8 O6 Cu1 Cu1 4.63(12) . . . 7_556 ? C1 O1 Cu1 O6 -85.90(13) . . . . ? C1 O1 Cu1 O2 -0.5(4) . . . 7_556 ? C1 O1 Cu1 O7 83.68(13) . . . 7_556 ? C1 O1 Cu1 O9 177.45(12) . . . . ? C1 O1 Cu1 Cu1 -1.03(12) . . . 7_556 ? 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 O5 H1O O10 0.839(19) 1.76(2) 2.5909(19) 172(3) 6 O9 H2O O12 0.870(19) 1.968(9) 2.811(4) 163(3) . O9 H3O O4 0.870(13) 1.907(9) 2.7454(18) 161(3) 6_556 O10 H4O O4 0.870(13) 1.949(6) 2.8079(17) 169(3) . O10 H5O O1 0.868(16) 1.944(16) 2.8113(19) 179(3) . O10 H5O O3 0.868(16) 2.56(2) 3.0021(19) 112(2) . O11 H7O O7 0.870(1) 2.446(2) 2.932(3) 115.88(11) 7_556 O11 H7O O7 0.870(1) 2.446(2) 2.932(3) 115.88(11) 8_455 O11 H7O O8 0.870(1) 2.444(5) 3.314(5) 180.000(1) 7_556 O11A H6O1 O9 0.870(1) 1.93(3) 2.771(6) 163(11) 2 O11A H6O1 O12 0.870(1) 2.63(11) 3.059(7) 112(9) 6 O11A H7O1 O7 0.870(1) 2.525(4) 3.015(6) 116.4(4) 8_455 O11A H7O1 O8 0.870(1) 2.614(9) 3.322(7) 139.2(6) 7_556 O12 H8O O9 0.8698(10) 2.25(4) 2.993(4) 143(6) 5_556 O12 H8O O12 0.8698(10) 2.50(6) 3.111(10) 128(6) 5_556 O12 H9O O10 0.8698(10) 2.07(4) 2.838(4) 147(6) 6_556 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.949 _refine_diff_density_min -0.918 _refine_diff_density_rms 0.078 #===END data_rc07pj1 _database_code_depnum_ccdc_archive 'CCDC 780212' #TrackingRef '- combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 Cu N3 O3, Cl O4 ' _chemical_formula_sum 'C17 H20 Cl Cu N3 O7' _chemical_formula_weight 477.35 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 8.521(2) _cell_length_b 10.161(2) _cell_length_c 21.849(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.554(2) _cell_angle_gamma 90.00 _cell_volume 1875.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9746 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.31 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.691 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 980 _exptl_absorpt_coefficient_mu 1.355 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.810060 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 196 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0.14 _diffrn_reflns_number 17816 _diffrn_reflns_av_R_equivalents 0.0215 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4499 _reflns_number_gt 4010 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT (Bruker, 1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _refine_special_details ; The N-bound H atoms were refined with bond length restraints of 0.89(1) \A There is a Pseudo translation between metal containing complexes, however the positions of the water molecules are inconsistent with this. 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^)+(0.0331P)^2^+2.7187P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4499 _refine_ls_number_parameters 265 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0396 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_restrained_S_all 1.189 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.47388(3) 0.21188(3) 0.170088(13) 0.02165(9) Uani 1 1 d . . . Cl1 Cl 0.16598(8) 0.20228(7) 0.43928(3) 0.03351(16) Uani 1 1 d . . . O1 O 0.3386(2) 0.02248(18) 0.12245(8) 0.0304(4) Uani 1 1 d . . . O2 O 0.5027(2) 0.07968(17) 0.23535(8) 0.0244(4) Uani 1 1 d . . . O3 O 0.3958(2) -0.09112(19) 0.27809(9) 0.0300(4) Uani 1 1 d . . . O4 O 0.2416(3) 0.1755(3) 0.38642(12) 0.0610(7) Uani 1 1 d . . . O5 O 0.0126(3) 0.2552(3) 0.41937(16) 0.0719(9) Uani 1 1 d . . . O6 O 0.1504(4) 0.0832(3) 0.47233(13) 0.0728(9) Uani 1 1 d . . . O7 O 0.2571(3) 0.2947(2) 0.47959(11) 0.0501(6) Uani 1 1 d . . . N1 N 0.2744(2) 0.2890(2) 0.19400(10) 0.0238(4) Uani 1 1 d . . . N2 N 0.4309(3) 0.3358(2) 0.09870(11) 0.0321(5) Uani 1 1 d D . . H1N H 0.378(4) 0.296(3) 0.0665(11) 0.048 Uiso 1 1 d D . . N3 N 0.6730(2) 0.1797(2) 0.13403(10) 0.0237(4) Uani 1 1 d . . . C1 C 0.1909(3) 0.2459(3) 0.23796(13) 0.0314(6) Uani 1 1 d . . . H1 H 0.2316 0.1751 0.2637 0.038 Uiso 1 1 calc R . . C2 C 0.0474(3) 0.3012(3) 0.24707(15) 0.0391(7) Uani 1 1 d . . . H2 H -0.0100 0.2688 0.2783 0.047 Uiso 1 1 calc R . . C3 C -0.0107(3) 0.4051(3) 0.20963(16) 0.0416(7) Uani 1 1 d . . . H3 H -0.1102 0.4434 0.2141 0.050 Uiso 1 1 calc R . . C4 C 0.0774(3) 0.4521(3) 0.16584(14) 0.0372(7) Uani 1 1 d . . . H4 H 0.0406 0.5249 0.1407 0.045 Uiso 1 1 calc R . . C5 C 0.2199(3) 0.3924(3) 0.15874(12) 0.0267(5) Uani 1 1 d . . . C6 C 0.3263(4) 0.4411(3) 0.11417(14) 0.0343(6) Uani 1 1 d . . . H6A H 0.2614 0.4729 0.0761 0.041 Uiso 1 1 calc R . . H6B H 0.3904 0.5157 0.1327 0.041 Uiso 1 1 calc R . . C7 C 0.5796(3) 0.3751(3) 0.07784(13) 0.0332(6) Uani 1 1 d . . . H7A H 0.6197 0.4562 0.0997 0.040 Uiso 1 1 calc R . . H7B H 0.5618 0.3942 0.0330 0.040 Uiso 1 1 calc R . . C8 C 0.7011(3) 0.2662(3) 0.09048(12) 0.0260(5) Uani 1 1 d . . . C9 C 0.8356(3) 0.2591(3) 0.06096(13) 0.0321(6) Uani 1 1 d . . . H9 H 0.8545 0.3224 0.0308 0.039 Uiso 1 1 calc R . . C10 C 0.9414(3) 0.1575(3) 0.07647(14) 0.0374(7) Uani 1 1 d . . . H10 H 1.0338 0.1496 0.0567 0.045 Uiso 1 1 calc R . . C11 C 0.9118(3) 0.0680(3) 0.12074(15) 0.0387(7) Uani 1 1 d . . . H11 H 0.9832 -0.0025 0.1317 0.046 Uiso 1 1 calc R . . C12 C 0.7774(3) 0.0817(3) 0.14919(14) 0.0328(6) Uani 1 1 d . . . H12 H 0.7580 0.0205 0.1802 0.039 Uiso 1 1 calc R . . C13 C 0.3795(4) -0.0426(3) 0.06796(14) 0.0419(7) Uani 1 1 d . . . H13A H 0.4856 -0.0142 0.0594 0.050 Uiso 1 1 calc R . . H13B H 0.3014 -0.0207 0.0317 0.050 Uiso 1 1 calc R . . C14 C 0.3786(4) -0.1882(3) 0.08033(14) 0.0390(7) Uani 1 1 d . . . H14A H 0.4575 -0.2347 0.0588 0.047 Uiso 1 1 calc R . . H14B H 0.2726 -0.2267 0.0677 0.047 Uiso 1 1 calc R . . C15 C 0.4229(5) -0.1931(3) 0.14971(15) 0.0468(8) Uani 1 1 d . . . H15A H 0.5388 -0.1856 0.1614 0.056 Uiso 1 1 calc R . . H15B H 0.3850 -0.2752 0.1673 0.056 Uiso 1 1 calc R . . C16 C 0.3366(3) -0.0728(3) 0.17052(12) 0.0284(5) Uani 1 1 d . . . H16 H 0.2245 -0.0970 0.1742 0.034 Uiso 1 1 calc R . . C17 C 0.4173(3) -0.0238(2) 0.23289(11) 0.0235(5) 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 Cu1 0.02277(15) 0.01878(15) 0.02360(16) 0.00223(11) 0.00380(11) 0.00380(11) Cl1 0.0390(4) 0.0287(3) 0.0336(3) -0.0031(3) 0.0075(3) -0.0044(3) O1 0.0399(11) 0.0251(9) 0.0254(9) 0.0006(7) 0.0013(8) 0.0019(8) O2 0.0275(9) 0.0203(8) 0.0243(8) 0.0001(7) -0.0001(7) 0.0005(7) O3 0.0326(10) 0.0283(9) 0.0303(9) 0.0054(7) 0.0088(8) 0.0019(8) O4 0.0623(16) 0.080(2) 0.0435(14) -0.0116(13) 0.0185(12) -0.0120(15) O5 0.0441(15) 0.0669(19) 0.101(2) -0.0135(18) -0.0026(15) 0.0076(13) O6 0.128(3) 0.0390(14) 0.0519(16) 0.0056(12) 0.0137(17) -0.0195(16) O7 0.0594(15) 0.0396(13) 0.0488(14) -0.0095(10) -0.0025(11) -0.0106(11) N1 0.0210(9) 0.0219(10) 0.0278(10) -0.0040(8) 0.0009(8) 0.0012(8) N2 0.0359(13) 0.0278(12) 0.0332(12) 0.0047(9) 0.0065(10) 0.0069(10) N3 0.0219(10) 0.0225(10) 0.0267(10) -0.0019(8) 0.0027(8) 0.0010(8) C1 0.0309(13) 0.0270(13) 0.0374(14) -0.0032(11) 0.0086(11) 0.0000(11) C2 0.0319(14) 0.0389(16) 0.0498(17) -0.0137(14) 0.0170(13) -0.0031(12) C3 0.0258(13) 0.0444(17) 0.0544(19) -0.0182(15) 0.0043(13) 0.0078(12) C4 0.0310(14) 0.0367(15) 0.0414(16) -0.0079(13) -0.0048(12) 0.0123(12) C5 0.0262(12) 0.0231(12) 0.0291(12) -0.0065(10) -0.0031(10) 0.0045(10) C6 0.0376(15) 0.0295(14) 0.0355(14) 0.0073(11) 0.0040(12) 0.0114(12) C7 0.0385(15) 0.0285(13) 0.0336(14) 0.0075(11) 0.0090(11) 0.0018(11) C8 0.0273(12) 0.0249(12) 0.0254(12) -0.0038(9) 0.0023(10) -0.0032(10) C9 0.0318(14) 0.0362(15) 0.0295(13) -0.0039(11) 0.0083(11) -0.0072(11) C10 0.0260(13) 0.0474(17) 0.0400(15) -0.0125(13) 0.0087(11) -0.0020(12) C11 0.0274(13) 0.0394(16) 0.0499(18) -0.0040(13) 0.0072(12) 0.0085(12) C12 0.0279(13) 0.0297(14) 0.0404(15) 0.0030(11) 0.0029(11) 0.0053(11) C13 0.062(2) 0.0348(16) 0.0297(14) -0.0037(12) 0.0081(14) -0.0013(14) C14 0.0474(17) 0.0318(15) 0.0372(15) -0.0075(12) 0.0028(13) 0.0051(13) C15 0.075(2) 0.0276(15) 0.0352(16) -0.0049(12) -0.0005(15) 0.0129(15) C16 0.0274(12) 0.0268(13) 0.0313(13) 0.0014(10) 0.0049(10) -0.0022(10) C17 0.0231(11) 0.0213(12) 0.0270(12) -0.0002(9) 0.0063(9) 0.0050(9) _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 O2 1.9509(17) . ? Cu1 N3 1.989(2) . ? Cu1 N2 2.001(2) . ? Cu1 N1 2.002(2) . ? Cu1 O1 2.4082(19) . ? Cu1 O3 2.4883(19) 2_655 ? Cl1 O4 1.421(3) . ? Cl1 O6 1.425(3) . ? Cl1 O5 1.427(3) . ? Cl1 O7 1.442(2) . ? O1 C16 1.430(3) . ? O1 C13 1.444(3) . ? O2 C17 1.276(3) . ? O3 C17 1.235(3) . ? N1 C1 1.342(4) . ? N1 C5 1.349(3) . ? N2 C7 1.458(4) . ? N2 C6 1.460(4) . ? N2 H1N 0.88(3) . ? N3 C8 1.341(3) . ? N3 C12 1.347(3) . ? C1 C2 1.383(4) . ? C1 H1 0.9500 . ? C2 C3 1.386(5) . ? C2 H2 0.9500 . ? C3 C4 1.377(5) . ? C3 H3 0.9500 . ? C4 C5 1.384(4) . ? C4 H4 0.9500 . ? C5 C6 1.499(4) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.515(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.389(4) . ? C9 C10 1.383(4) . ? C9 H9 0.9500 . ? C10 C11 1.375(5) . ? C10 H10 0.9500 . ? C11 C12 1.380(4) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.504(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.514(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.526(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.527(4) . ? C16 H16 1.0000 . ? 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 Cu1 N3 98.28(8) . . ? O2 Cu1 N2 174.75(9) . . ? N3 Cu1 N2 82.72(9) . . ? O2 Cu1 N1 96.21(8) . . ? N3 Cu1 N1 164.83(9) . . ? N2 Cu1 N1 83.25(9) . . ? O2 Cu1 O1 76.86(7) . . ? N3 Cu1 O1 94.69(8) . . ? N2 Cu1 O1 97.93(9) . . ? N1 Cu1 O1 92.92(8) . . ? O2 Cu1 O3 102.45(7) . 2_655 ? N3 Cu1 O3 87.69(7) . 2_655 ? N2 Cu1 O3 82.72(9) . 2_655 ? N1 Cu1 O3 84.84(7) . 2_655 ? O1 Cu1 O3 177.58(6) . 2_655 ? O4 Cl1 O6 109.37(19) . . ? O4 Cl1 O5 108.64(19) . . ? O6 Cl1 O5 109.4(2) . . ? O4 Cl1 O7 110.85(16) . . ? O6 Cl1 O7 108.80(16) . . ? O5 Cl1 O7 109.79(17) . . ? C16 O1 C13 108.8(2) . . ? C16 O1 Cu1 105.96(14) . . ? C13 O1 Cu1 124.68(18) . . ? C17 O2 Cu1 121.36(16) . . ? C1 N1 C5 119.2(2) . . ? C1 N1 Cu1 127.43(18) . . ? C5 N1 Cu1 113.32(17) . . ? C7 N2 C6 117.0(2) . . ? C7 N2 Cu1 109.77(17) . . ? C6 N2 Cu1 109.60(17) . . ? C7 N2 H1N 104(2) . . ? C6 N2 H1N 105(2) . . ? Cu1 N2 H1N 111(2) . . ? C8 N3 C12 119.0(2) . . ? C8 N3 Cu1 114.49(17) . . ? C12 N3 Cu1 126.47(19) . . ? N1 C1 C2 122.2(3) . . ? N1 C1 H1 118.9 . . ? C2 C1 H1 118.9 . . ? C1 C2 C3 118.6(3) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.5(3) . . ? C3 C4 H4 120.3 . . ? C5 C4 H4 120.3 . . ? N1 C5 C4 121.2(3) . . ? N1 C5 C6 115.9(2) . . ? C4 C5 C6 122.8(3) . . ? N2 C6 C5 110.4(2) . . ? N2 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? N2 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? N2 C7 C8 110.2(2) . . ? N2 C7 H7A 109.6 . . ? C8 C7 H7A 109.6 . . ? N2 C7 H7B 109.6 . . ? C8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C9 122.1(2) . . ? N3 C8 C7 115.3(2) . . ? C9 C8 C7 122.6(2) . . ? C10 C9 C8 118.5(3) . . ? C10 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? C11 C10 C9 119.5(3) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C10 C11 C12 119.4(3) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? N3 C12 C11 121.6(3) . . ? N3 C12 H12 119.2 . . ? C11 C12 H12 119.2 . . ? O1 C13 C14 107.2(2) . . ? O1 C13 H13A 110.3 . . ? C14 C13 H13A 110.3 . . ? O1 C13 H13B 110.3 . . ? C14 C13 H13B 110.3 . . ? H13A C13 H13B 108.5 . . ? C13 C14 C15 101.9(2) . . ? C13 C14 H14A 111.4 . . ? C15 C14 H14A 111.4 . . ? C13 C14 H14B 111.4 . . ? C15 C14 H14B 111.4 . . ? H14A C14 H14B 109.3 . . ? C14 C15 C16 101.9(2) . . ? C14 C15 H15A 111.4 . . ? C16 C15 H15A 111.4 . . ? C14 C15 H15B 111.4 . . ? C16 C15 H15B 111.4 . . ? H15A C15 H15B 109.3 . . ? O1 C16 C15 105.7(2) . . ? O1 C16 C17 112.8(2) . . ? C15 C16 C17 110.4(2) . . ? O1 C16 H16 109.3 . . ? C15 C16 H16 109.3 . . ? C17 C16 H16 109.3 . . ? O3 C17 O2 124.5(2) . . ? O3 C17 C16 115.9(2) . . ? O2 C17 C16 119.6(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu1 O1 C16 7.72(15) . . . . ? N3 Cu1 O1 C16 105.15(16) . . . . ? N2 Cu1 O1 C16 -171.57(16) . . . . ? N1 Cu1 O1 C16 -87.99(16) . . . . ? O2 Cu1 O1 C13 -119.6(2) . . . . ? N3 Cu1 O1 C13 -22.2(2) . . . . ? N2 Cu1 O1 C13 61.1(2) . . . . ? N1 Cu1 O1 C13 144.7(2) . . . . ? N3 Cu1 O2 C17 -109.66(18) . . . . ? N1 Cu1 O2 C17 74.82(19) . . . . ? O1 Cu1 O2 C17 -16.74(18) . . . . ? O3 Cu1 O2 C17 160.89(17) 2_655 . . . ? O2 Cu1 N1 C1 -5.5(2) . . . . ? N3 Cu1 N1 C1 -168.4(3) . . . . ? N2 Cu1 N1 C1 169.2(2) . . . . ? O1 Cu1 N1 C1 71.6(2) . . . . ? O3 Cu1 N1 C1 -107.5(2) 2_655 . . . ? O2 Cu1 N1 C5 177.33(17) . . . . ? N3 Cu1 N1 C5 14.5(4) . . . . ? N2 Cu1 N1 C5 -7.93(17) . . . . ? O1 Cu1 N1 C5 -105.58(17) . . . . ? O3 Cu1 N1 C5 75.33(17) 2_655 . . . ? N3 Cu1 N2 C7 -23.24(19) . . . . ? N1 Cu1 N2 C7 151.0(2) . . . . ? O1 Cu1 N2 C7 -117.00(19) . . . . ? O3 Cu1 N2 C7 65.35(19) 2_655 . . . ? N3 Cu1 N2 C6 -153.1(2) . . . . ? N1 Cu1 N2 C6 21.14(19) . . . . ? O1 Cu1 N2 C6 113.16(19) . . . . ? O3 Cu1 N2 C6 -64.49(19) 2_655 . . . ? O2 Cu1 N3 C8 -173.05(17) . . . . ? N2 Cu1 N3 C8 12.15(18) . . . . ? N1 Cu1 N3 C8 -10.3(4) . . . . ? O1 Cu1 N3 C8 109.57(17) . . . . ? O3 Cu1 N3 C8 -70.80(18) 2_655 . . . ? O2 Cu1 N3 C12 7.1(2) . . . . ? N2 Cu1 N3 C12 -167.7(2) . . . . ? N1 Cu1 N3 C12 169.8(3) . . . . ? O1 Cu1 N3 C12 -70.3(2) . . . . ? O3 Cu1 N3 C12 109.3(2) 2_655 . . . ? C5 N1 C1 C2 2.2(4) . . . . ? Cu1 N1 C1 C2 -174.7(2) . . . . ? N1 C1 C2 C3 -0.4(4) . . . . ? C1 C2 C3 C4 -1.7(4) . . . . ? C2 C3 C4 C5 1.9(4) . . . . ? C1 N1 C5 C4 -2.0(4) . . . . ? Cu1 N1 C5 C4 175.4(2) . . . . ? C1 N1 C5 C6 175.3(2) . . . . ? Cu1 N1 C5 C6 -7.3(3) . . . . ? C3 C4 C5 N1 -0.1(4) . . . . ? C3 C4 C5 C6 -177.2(3) . . . . ? C7 N2 C6 C5 -155.5(2) . . . . ? Cu1 N2 C6 C5 -29.7(3) . . . . ? N1 C5 C6 N2 24.9(3) . . . . ? C4 C5 C6 N2 -157.8(3) . . . . ? C6 N2 C7 C8 155.2(2) . . . . ? Cu1 N2 C7 C8 29.5(3) . . . . ? C12 N3 C8 C9 -0.8(4) . . . . ? Cu1 N3 C8 C9 179.3(2) . . . . ? C12 N3 C8 C7 -178.3(2) . . . . ? Cu1 N3 C8 C7 1.8(3) . . . . ? N2 C7 C8 N3 -21.0(3) . . . . ? N2 C7 C8 C9 161.4(2) . . . . ? N3 C8 C9 C10 1.3(4) . . . . ? C7 C8 C9 C10 178.7(3) . . . . ? C8 C9 C10 C11 -0.7(4) . . . . ? C9 C10 C11 C12 -0.4(5) . . . . ? C8 N3 C12 C11 -0.4(4) . . . . ? Cu1 N3 C12 C11 179.5(2) . . . . ? C10 C11 C12 N3 0.9(5) . . . . ? C16 O1 C13 C14 8.7(3) . . . . ? Cu1 O1 C13 C14 134.8(2) . . . . ? O1 C13 C14 C15 -29.2(4) . . . . ? C13 C14 C15 C16 37.2(3) . . . . ? C13 O1 C16 C15 15.6(3) . . . . ? Cu1 O1 C16 C15 -120.7(2) . . . . ? C13 O1 C16 C17 136.3(2) . . . . ? Cu1 O1 C16 C17 0.0(2) . . . . ? C14 C15 C16 O1 -33.3(3) . . . . ? C14 C15 C16 C17 -155.5(3) . . . . ? Cu1 O2 C17 O3 -158.27(19) . . . . ? Cu1 O2 C17 C16 23.0(3) . . . . ? O1 C16 C17 O3 167.8(2) . . . . ? C15 C16 C17 O3 -74.2(3) . . . . ? O1 C16 C17 O2 -13.4(3) . . . . ? C15 C16 C17 O2 104.6(3) . . . . ? 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 N2 H1N O7 0.88(3) 2.24(3) 3.117(4) 175(3) 4_565 _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.746 _refine_diff_density_min -0.458 _refine_diff_density_rms 0.074 #===END data_rc8jc7s _database_code_depnum_ccdc_archive 'CCDC 780213' #TrackingRef '- combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C7 H10 Cu O10' _chemical_formula_sum 'C7 H10 Cu O10' _chemical_formula_weight 317.69 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.9663(17) _cell_length_b 9.909(3) _cell_length_c 10.491(4) _cell_angle_alpha 94.104(6) _cell_angle_beta 94.908(6) _cell_angle_gamma 97.222(6) _cell_volume 508.5(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3266 _cell_measurement_theta_min 2.722 _cell_measurement_theta_max 28.244 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.075 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 2.199 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.529 _exptl_absorpt_correction_T_max 0.643 _exptl_absorpt_process_details 'TWINABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. The structure is twinned by a 180 \o rotation around -0.001 1.000 0.001 corresponding to the following twin law: -1.000 -0.001 0.000 0.530 1.000 0.155 0.001 0.002 -1.000. component 1 2093 single reflections component 2 2036 single reflections Rint = 0.0284 for all 7906 observations The O-bound H atoms were refined with bond length restraints of 0.840(1) \A ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'BRUKER SMART 1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 0 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2350 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0215 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 28.32 _reflns_number_total 2350 _reflns_number_gt 2122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1995)' _computing_cell_refinement 'SAINT and CELL_NOW (Bruker, 1995)' _computing_data_reduction 'SAINT and XPREP (Bruker, 1995)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.0 (CCDC, 2003)' _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^)+(0.0408P)^2^+0.2603P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2350 _refine_ls_number_parameters 191 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0257 _refine_ls_wR_factor_ref 0.0675 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7947(5) 0.2323(2) 0.0692(2) 0.0139(4) Uani 1 1 d . . . C2 C 0.6224(4) 0.1439(2) 0.1523(2) 0.0115(4) Uani 1 1 d . . . C3 C 0.3011(4) 0.1428(2) 0.3020(2) 0.0123(4) Uani 1 1 d . . . C4 C 0.2964(5) 0.0081(2) 0.3126(2) 0.0153(4) Uani 1 1 d . . . H4 H 0.1843 -0.0360 0.3704 0.018 Uiso 1 1 calc R . . C5 C 0.4609(5) -0.0695(2) 0.2366(2) 0.0162(4) Uani 1 1 d . . . C6 C 0.6297(5) 0.0087(2) 0.1556(2) 0.0137(4) Uani 1 1 d . . . H6 H 0.7467 -0.0354 0.1042 0.016 Uiso 1 1 calc R . . C7 C 0.1243(4) 0.2333(2) 0.3704(2) 0.0121(4) Uani 1 1 d . . . O1 O 0.7481(3) 0.35584(16) 0.06634(16) 0.0133(3) Uani 1 1 d . . . O2 O 0.9659(4) 0.17730(18) 0.0146(2) 0.0282(4) Uani 1 1 d . . . O3 O 0.4618(3) 0.21311(15) 0.22421(15) 0.0119(3) Uani 1 1 d . . . O4 O 0.4548(4) -0.19670(18) 0.23729(18) 0.0272(4) Uani 1 1 d . . . O5 O 0.1444(3) 0.35607(16) 0.34230(15) 0.0150(3) Uani 1 1 d . . . O6 O -0.0282(4) 0.17915(17) 0.44521(17) 0.0191(4) Uani 1 1 d . . . O7 O 0.7024(3) 0.52771(16) -0.12854(15) 0.0134(3) Uani 1 1 d D . . H2O H 0.569(4) 0.564(3) -0.106(3) 0.020 Uiso 1 1 d D . . H1O H 0.748(6) 0.562(3) -0.1957(16) 0.020 Uiso 1 1 d D . . O8 O 0.8631(4) 0.64890(18) 0.17340(18) 0.0234(4) Uani 1 1 d D . . H4O H 1.006(4) 0.704(3) 0.174(3) 0.035 Uiso 1 1 d D . . H3O H 0.728(4) 0.691(3) 0.164(4) 0.035 Uiso 1 1 d D . . O9 O 0.7625(3) 0.51022(18) 0.37682(16) 0.0182(3) Uani 1 1 d D . . H6O H 0.789(6) 0.561(3) 0.317(2) 0.027 Uiso 1 1 d D . . H5O H 0.888(4) 0.461(3) 0.373(3) 0.027 Uiso 1 1 d D . . O10 O 0.3745(3) 0.67010(17) 0.44920(16) 0.0170(3) Uani 1 1 d D . . H8O H 0.412(6) 0.706(3) 0.3815(17) 0.026 Uiso 1 1 d D . . H7O H 0.258(5) 0.712(3) 0.483(3) 0.026 Uiso 1 1 d D . . Cu1 Cu 1.0000 0.5000 0.0000 0.01047(10) Uani 1 2 d S . . Cu2 Cu 0.5000 0.5000 0.5000 0.01093(10) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0140(10) 0.0126(10) 0.0155(10) 0.0023(8) 0.0046(8) 0.0007(8) C2 0.0107(9) 0.0124(10) 0.0119(10) 0.0014(8) 0.0035(8) 0.0021(8) C3 0.0126(10) 0.0137(10) 0.0115(10) 0.0020(8) 0.0050(8) 0.0021(8) C4 0.0188(11) 0.0131(11) 0.0156(11) 0.0039(8) 0.0077(9) 0.0023(8) C5 0.0231(12) 0.0116(10) 0.0149(11) 0.0039(8) 0.0048(9) 0.0023(9) C6 0.0157(10) 0.0128(10) 0.0142(10) 0.0027(8) 0.0056(8) 0.0042(8) C7 0.0115(10) 0.0125(10) 0.0127(10) 0.0007(8) 0.0017(8) 0.0029(8) O1 0.0129(7) 0.0115(7) 0.0170(7) 0.0054(6) 0.0050(6) 0.0032(6) O2 0.0339(11) 0.0153(8) 0.0418(11) 0.0079(8) 0.0279(9) 0.0082(8) O3 0.0128(7) 0.0102(7) 0.0142(7) 0.0030(6) 0.0069(6) 0.0026(6) O4 0.0494(12) 0.0106(8) 0.0270(10) 0.0077(7) 0.0217(9) 0.0090(8) O5 0.0176(8) 0.0129(7) 0.0165(8) 0.0034(6) 0.0060(6) 0.0054(6) O6 0.0209(8) 0.0168(8) 0.0227(9) 0.0055(7) 0.0135(7) 0.0052(7) O7 0.0121(7) 0.0144(8) 0.0155(7) 0.0057(6) 0.0046(6) 0.0041(6) O8 0.0303(10) 0.0139(8) 0.0288(10) 0.0055(7) 0.0162(8) 0.0024(7) O9 0.0186(8) 0.0205(9) 0.0201(8) 0.0099(7) 0.0104(6) 0.0100(7) O10 0.0208(8) 0.0165(8) 0.0182(8) 0.0080(6) 0.0116(7) 0.0097(6) Cu1 0.00948(16) 0.01003(17) 0.01299(18) 0.00474(15) 0.00347(12) 0.00173(15) Cu2 0.01135(17) 0.01071(18) 0.01249(18) 0.00361(15) 0.00508(12) 0.00413(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.227(3) . ? C1 O1 1.276(3) . ? C1 C2 1.520(3) . ? C2 C6 1.348(3) . ? C2 O3 1.357(3) . ? C3 C4 1.344(3) . ? C3 O3 1.357(3) . ? C3 C7 1.519(3) . ? C4 C5 1.441(3) . ? C4 H4 0.9500 . ? C5 O4 1.258(3) . ? C5 C6 1.441(3) . ? C6 H6 0.9500 . ? C7 O6 1.240(3) . ? C7 O5 1.266(3) . ? O1 Cu1 1.9827(16) . ? O5 Cu2 2.5336(18) . ? O7 Cu1 1.9730(16) . ? O7 H2O 0.84(2) . ? O7 H1O 0.84(2) . ? O8 Cu1 2.4552(19) . ? O8 H4O 0.84(2) . ? O8 H3O 0.84(2) . ? O9 Cu2 1.9113(16) . ? O9 H6O 0.84(2) . ? O9 H5O 0.84(2) . ? O10 Cu2 1.9620(17) . ? O10 H8O 0.84(2) . ? O10 H7O 0.84(2) . ? Cu1 O7 1.9730(16) 2_765 ? Cu1 O1 1.9827(16) 2_765 ? Cu2 O9 1.9113(16) 2_666 ? Cu2 O10 1.9620(17) 2_666 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 127.6(2) . . ? O2 C1 C2 116.2(2) . . ? O1 C1 C2 116.26(19) . . ? C6 C2 O3 122.71(19) . . ? C6 C2 C1 123.11(19) . . ? O3 C2 C1 114.18(17) . . ? C4 C3 O3 123.1(2) . . ? C4 C3 C7 124.96(19) . . ? O3 C3 C7 111.87(18) . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? O4 C5 C6 121.7(2) . . ? O4 C5 C4 123.1(2) . . ? C6 C5 C4 115.14(19) . . ? C2 C6 C5 120.4(2) . . ? C2 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? O6 C7 O5 126.9(2) . . ? O6 C7 C3 117.03(19) . . ? O5 C7 C3 116.02(18) . . ? C1 O1 Cu1 123.13(14) . . ? C3 O3 C2 118.46(16) . . ? C7 O5 Cu2 109.13(13) . . ? Cu1 O7 H2O 120(2) . . ? Cu1 O7 H1O 117(2) . . ? H2O O7 H1O 107(3) . . ? Cu1 O8 H4O 92(2) . . ? Cu1 O8 H3O 123(3) . . ? H4O O8 H3O 109(3) . . ? Cu2 O9 H6O 133(2) . . ? Cu2 O9 H5O 125(2) . . ? H6O O9 H5O 102(3) . . ? Cu2 O10 H8O 124(2) . . ? Cu2 O10 H7O 127(2) . . ? H8O O10 H7O 109(3) . . ? O7 Cu1 O7 180.00(9) 2_765 . ? O7 Cu1 O1 88.71(7) 2_765 2_765 ? O7 Cu1 O1 91.29(7) . 2_765 ? O7 Cu1 O1 91.29(7) 2_765 . ? O7 Cu1 O1 88.71(7) . . ? O1 Cu1 O1 180.0 2_765 . ? O7 Cu1 O8 84.23(7) 2_765 . ? O7 Cu1 O8 95.77(7) . . ? O1 Cu1 O8 95.50(6) 2_765 . ? O1 Cu1 O8 84.50(6) . . ? O9 Cu2 O9 180.000(1) . 2_666 ? O9 Cu2 O10 91.09(7) . . ? O9 Cu2 O10 88.91(7) 2_666 . ? O9 Cu2 O10 88.91(7) . 2_666 ? O9 Cu2 O10 91.09(7) 2_666 2_666 ? O10 Cu2 O10 180.00(9) . 2_666 ? O9 Cu2 O5 92.17(7) . . ? O9 Cu2 O5 87.83(7) 2_666 . ? O10 Cu2 O5 92.10(7) . . ? O10 Cu2 O5 87.90(7) 2_666 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C6 -7.8(3) . . . . ? O1 C1 C2 C6 173.5(2) . . . . ? O2 C1 C2 O3 171.6(2) . . . . ? O1 C1 C2 O3 -7.0(3) . . . . ? O3 C3 C4 C5 -1.9(4) . . . . ? C7 C3 C4 C5 176.0(2) . . . . ? C3 C4 C5 O4 -176.2(2) . . . . ? C3 C4 C5 C6 2.0(3) . . . . ? O3 C2 C6 C5 0.7(3) . . . . ? C1 C2 C6 C5 -180.0(2) . . . . ? O4 C5 C6 C2 176.9(2) . . . . ? C4 C5 C6 C2 -1.4(3) . . . . ? C4 C3 C7 O6 2.8(3) . . . . ? O3 C3 C7 O6 -179.17(19) . . . . ? C4 C3 C7 O5 -175.6(2) . . . . ? O3 C3 C7 O5 2.5(3) . . . . ? O2 C1 O1 Cu1 -13.5(4) . . . . ? C2 C1 O1 Cu1 165.03(14) . . . . ? C4 C3 O3 C2 1.0(3) . . . . ? C7 C3 O3 C2 -177.11(17) . . . . ? C6 C2 O3 C3 -0.4(3) . . . . ? C1 C2 O3 C3 -179.77(18) . . . . ? O6 C7 O5 Cu2 89.0(2) . . . . ? C3 C7 O5 Cu2 -92.78(18) . . . . ? C1 O1 Cu1 O7 -59.40(18) . . . 2_765 ? C1 O1 Cu1 O7 120.60(18) . . . . ? C1 O1 Cu1 O8 -143.47(18) . . . . ? C7 O5 Cu2 O9 104.26(14) . . . . ? C7 O5 Cu2 O9 -75.74(14) . . . 2_666 ? C7 O5 Cu2 O10 -164.57(14) . . . . ? C7 O5 Cu2 O10 15.43(14) . . . 2_666 ? 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 H2O O1 0.84(2) 1.91(2) 2.748(2) 176(3) 2_665 O7 H1O O3 0.84(2) 2.60(3) 3.004(2) 111(2) 2_665 O7 H1O O5 0.84(2) 1.88(2) 2.716(2) 178(3) 2_665 O7 H1O O3 0.84(2) 2.60(3) 3.004(2) 111(2) 2_665 O8 H4O O2 0.84(2)) 2.38(3) 2.825(3) 114(3) 2_765 O8 H3O O4 0.84(2) 2.021(18) 2.787(3) 151(3) 1_565 O9 H6O O8 0.84(2) 1.84(2) 2.669(2) 172(3) . O9 H5O O5 0.84(2) 1.78(2) 2.613(2) 172(3) 1_655 O10 H8O O4 0.84(2) 1.86(2) 2.699(2) 171(3) 1_565 O10 H7O O6 0.84(2) 1.84(3) 2.674(2) 174(3) 2_566 _diffrn_measured_fraction_theta_max 0.931 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.492 _refine_diff_density_min -0.682 _refine_diff_density_rms 0.083 #===END data_rc8jc11 _database_code_depnum_ccdc_archive 'CCDC 780214' #TrackingRef '- combined.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Ni O16' _chemical_formula_sum 'C14 H14 Ni O16' _chemical_formula_weight 496.96 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Ni Ni 0.3393 1.1124 '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' _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.1607(3) _cell_length_b 5.8504(3) _cell_length_c 14.5170(7) _cell_angle_alpha 100.254(3) _cell_angle_beta 95.110(3) _cell_angle_gamma 90.761(3) _cell_volume 429.40(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2571 _cell_measurement_theta_min 3.550 _cell_measurement_theta_max 29.872 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.922 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 254 _exptl_absorpt_coefficient_mu 1.225 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.787 _exptl_absorpt_correction_T_max 0.863 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _exptl_special_details ; The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type APEXII-FR591 _diffrn_measurement_method \w+\f _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5904 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0406 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 29.88 _reflns_number_total 2184 _reflns_number_gt 1900 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX (Bruker-Nonius, 2003)' _computing_cell_refinement 'SAINT (Bruker-Nonius, 2003)' _computing_data_reduction 'SAINT (Bruker-Nonius, 2003), XPREP (Bruker-Nonius, 2003)' _computing_structure_solution 'SIR97 (Altomare, et. al. 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ;ORTEP-3 (Farrugia, 1997) WINGX-32 (Farrugia, 1999) ; _computing_publication_material 'enCIFer 1.1 (CCDC, 2005)' _refine_special_details ; The O-bound H atoms were refined with bond length restraints of 0.84(1) \A 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^)+(0.0248P)^2^+0.3162P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2184 _refine_ls_number_parameters 157 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_ref 0.0693 _refine_ls_wR_factor_gt 0.0652 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0584(4) 0.2651(3) 0.34623(13) 0.0101(4) Uani 1 1 d . . . C2 C 0.1987(4) 0.3041(3) 0.26217(13) 0.0100(4) Uani 1 1 d . . . C3 C 0.5140(4) 0.1585(3) 0.16416(13) 0.0110(4) Uani 1 1 d . . . C4 C 0.4745(4) 0.3217(3) 0.10995(13) 0.0131(4) Uani 1 1 d . . . H4 H 0.5753 0.3242 0.0584 0.016 Uiso 1 1 calc R . . C5 C 0.2770(4) 0.4943(3) 0.13056(14) 0.0128(4) Uani 1 1 d . . . C6 C 0.1458(4) 0.4756(3) 0.21332(14) 0.0135(4) Uani 1 1 d . . . H6 H 0.0204 0.5864 0.2334 0.016 Uiso 1 1 calc R . . C7 C 0.7106(4) -0.0280(3) 0.15601(14) 0.0126(4) Uani 1 1 d . . . O1 O 0.1653(3) 0.1331(2) 0.39667(9) 0.0130(3) Uani 1 1 d . . . O2 O -0.1543(3) 0.3645(2) 0.35538(9) 0.0127(3) Uani 1 1 d . . . O3 O 0.3778(3) 0.1423(2) 0.23917(9) 0.0111(3) Uani 1 1 d . . . O4 O 0.7400(3) -0.1510(3) 0.21478(10) 0.0195(3) Uani 1 1 d . . . O5 O 0.8464(3) -0.0397(3) 0.08260(10) 0.0174(3) Uani 1 1 d . . . H1O H 0.958(5) -0.148(5) 0.0858(17) 0.026 Uiso 1 1 d . . . O6 O 0.2253(3) 0.6454(2) 0.08077(10) 0.0174(3) Uani 1 1 d . . . O7 O 0.2828(3) 0.1890(3) 0.59786(10) 0.0132(3) Uani 1 1 d . . . H2O H 0.306(5) 0.137(4) 0.6405(18) 0.020 Uiso 1 1 d . . . H3O H 0.241(5) 0.320(5) 0.6158(17) 0.020 Uiso 1 1 d . . . O8 O 0.2489(3) -0.2686(2) 0.47578(10) 0.0138(3) Uani 1 1 d . . . H4O H 0.276(5) -0.324(4) 0.5212(18) 0.021 Uiso 1 1 d . . . H5O H 0.398(5) -0.228(4) 0.4601(17) 0.021 Uiso 1 1 d . . . Ni1 Ni 0.0000 0.0000 0.5000 0.00968(11) Uani 1 2 d S . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0109(10) 0.0103(9) 0.0085(9) 0.0003(7) 0.0010(8) -0.0012(7) C2 0.0089(9) 0.0113(9) 0.0099(9) 0.0010(7) 0.0031(8) 0.0032(7) C3 0.0106(10) 0.0146(9) 0.0079(9) 0.0014(7) 0.0028(8) 0.0009(7) C4 0.0128(10) 0.0172(10) 0.0101(9) 0.0027(8) 0.0049(8) 0.0025(8) C5 0.0134(10) 0.0135(9) 0.0124(10) 0.0038(8) 0.0025(8) 0.0015(7) C6 0.0133(10) 0.0160(10) 0.0131(10) 0.0050(8) 0.0050(8) 0.0062(8) C7 0.0122(10) 0.0145(9) 0.0105(9) 0.0002(8) 0.0012(8) 0.0011(7) O1 0.0128(7) 0.0150(7) 0.0133(7) 0.0066(6) 0.0042(6) 0.0042(5) O2 0.0100(7) 0.0149(7) 0.0143(7) 0.0037(6) 0.0040(6) 0.0034(5) O3 0.0118(7) 0.0135(7) 0.0094(7) 0.0040(5) 0.0051(6) 0.0046(5) O4 0.0232(8) 0.0229(8) 0.0158(8) 0.0084(6) 0.0077(7) 0.0126(6) O5 0.0178(8) 0.0213(8) 0.0157(8) 0.0059(6) 0.0091(6) 0.0096(6) O6 0.0192(8) 0.0202(8) 0.0169(7) 0.0113(6) 0.0075(6) 0.0083(6) O7 0.0145(8) 0.0144(7) 0.0121(7) 0.0047(6) 0.0027(6) 0.0033(6) O8 0.0126(7) 0.0149(7) 0.0160(7) 0.0057(6) 0.0056(6) 0.0033(6) Ni1 0.00897(19) 0.01129(18) 0.01019(19) 0.00402(14) 0.00414(14) 0.00263(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 C1 O2 1.255(2) . ? C1 O1 1.256(2) . ? C1 C2 1.522(2) . ? C2 C6 1.345(3) . ? C2 O3 1.352(2) . ? C3 C4 1.348(3) . ? C3 O3 1.364(2) . ? C3 C7 1.496(3) . ? C4 C5 1.457(3) . ? C4 H4 0.9500 . ? C5 O6 1.255(2) . ? C5 C6 1.450(2) . ? C6 H6 0.9500 . ? C7 O4 1.211(2) . ? C7 O5 1.319(2) . ? O1 Ni1 2.0516(12) . ? O5 H1O 0.87(3) . ? O7 Ni1 2.0975(15) . ? O7 H2O 0.74(3) . ? O7 H3O 0.80(3) . ? O8 Ni1 2.0445(14) . ? O8 H4O 0.79(2) . ? O8 H5O 0.86(3) . ? Ni1 O8 2.0445(14) 2_556 ? Ni1 O1 2.0516(12) 2_556 ? Ni1 O7 2.0975(15) 2_556 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 127.76(16) . . ? O2 C1 C2 115.85(16) . . ? O1 C1 C2 116.36(17) . . ? C6 C2 O3 122.99(16) . . ? C6 C2 C1 124.18(17) . . ? O3 C2 C1 112.79(15) . . ? C4 C3 O3 123.82(18) . . ? C4 C3 C7 127.77(16) . . ? O3 C3 C7 108.39(15) . . ? C3 C4 C5 119.82(17) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? O6 C5 C6 123.16(18) . . ? O6 C5 C4 122.72(17) . . ? C6 C5 C4 114.13(16) . . ? C2 C6 C5 121.20(18) . . ? C2 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? O4 C7 O5 124.79(19) . . ? O4 C7 C3 120.70(17) . . ? O5 C7 C3 114.49(16) . . ? C1 O1 Ni1 126.03(12) . . ? C2 O3 C3 117.95(14) . . ? C7 O5 H1O 107.0(17) . . ? Ni1 O7 H2O 112(2) . . ? Ni1 O7 H3O 112.3(18) . . ? H2O O7 H3O 106(3) . . ? Ni1 O8 H4O 110.3(19) . . ? Ni1 O8 H5O 113.8(16) . . ? H4O O8 H5O 107(2) . . ? O8 Ni1 O8 180.000(1) . 2_556 ? O8 Ni1 O1 93.17(5) . 2_556 ? O8 Ni1 O1 86.83(5) 2_556 2_556 ? O8 Ni1 O1 86.83(5) . . ? O8 Ni1 O1 93.17(5) 2_556 . ? O1 Ni1 O1 180.0 2_556 . ? O8 Ni1 O7 89.99(6) . 2_556 ? O8 Ni1 O7 90.01(6) 2_556 2_556 ? O1 Ni1 O7 88.24(5) 2_556 2_556 ? O1 Ni1 O7 91.76(5) . 2_556 ? O8 Ni1 O7 90.01(6) . . ? O8 Ni1 O7 89.99(6) 2_556 . ? O1 Ni1 O7 91.76(5) 2_556 . ? O1 Ni1 O7 88.24(5) . . ? O7 Ni1 O7 180.00(8) 2_556 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 C1 C2 C6 16.9(3) . . . . ? O1 C1 C2 C6 -164.82(19) . . . . ? O2 C1 C2 O3 -160.88(16) . . . . ? O1 C1 C2 O3 17.4(2) . . . . ? O3 C3 C4 C5 0.1(3) . . . . ? C7 C3 C4 C5 -178.25(18) . . . . ? C3 C4 C5 O6 -177.50(19) . . . . ? C3 C4 C5 C6 2.4(3) . . . . ? O3 C2 C6 C5 1.2(3) . . . . ? C1 C2 C6 C5 -176.37(18) . . . . ? O6 C5 C6 C2 176.8(2) . . . . ? C4 C5 C6 C2 -3.1(3) . . . . ? C4 C3 C7 O4 173.5(2) . . . . ? O3 C3 C7 O4 -5.1(3) . . . . ? C4 C3 C7 O5 -5.0(3) . . . . ? O3 C3 C7 O5 176.39(16) . . . . ? O2 C1 O1 Ni1 9.3(3) . . . . ? C2 C1 O1 Ni1 -168.66(12) . . . . ? C6 C2 O3 C3 1.5(3) . . . . ? C1 C2 O3 C3 179.35(16) . . . . ? C4 C3 O3 C2 -2.2(3) . . . . ? C7 C3 O3 C2 176.44(16) . . . . ? C1 O1 Ni1 O8 153.95(16) . . . . ? C1 O1 Ni1 O8 -26.05(16) . . . 2_556 ? C1 O1 Ni1 O7 64.06(16) . . . 2_556 ? C1 O1 Ni1 O7 -115.94(16) . . . . ? 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 H2O O4 0.74(3) 2.12(3) 2.7808(19) 149(3) 2_656 O7 H3O O2 0.80(3) 1.89(3) 2.687(2) 173(2) 2_566 O8 H4O O2 0.79(2) 2.00(3) 2.6939(19) 146(2) 2_556 O8 H5O O7 0.86(3) 1.95(3) 2.7943(19) 168(2) 2_656 O5 H1O O6 0.87(3) 1.84(3) 2.703(2) 171(2) 1_645 _diffrn_measured_fraction_theta_max 0.854 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.98 _refine_diff_density_max 0.422 _refine_diff_density_min -0.515 _refine_diff_density_rms 0.080 #===END