Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Edward Wong' _publ_contact_author_address ; Department of Chemistry University of New Hampshire 225 Parsons Hall Durham New Hampshire 03824 UNITED STATES OF AMERICA ; _publ_contact_author_email EHW@CISUNIX.UNH.EDU _publ_section_title ; The long and short of it: the influence of N-carboxyethyl versus N-carboxymethyl pendant arms on in vitro and in vivo behavior of copper complexes of cross-bridged tetraamine macrocycles ; loop_ _publ_author_name 'Edward Wong' 'Carolyn J. Anderson' 'James A. Golen' 'Katie J. Heroux' 'Scott Kassel' ; A.L.Rheingold ; 'Evan Southwick' 'Sterling A. Tomellini' 'David J. Tranchemontagne' 'Thaddeus J. Wadas' ; G.Weisman ; 'Peter C. B. Widger' 'Katrina S. Woodin' #===END data_wong108 _database_code_depnum_ccdc_archive 'CCDC 635719' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16H28N4O4Cu, ClO4, Na, 3(H2O) ' _chemical_formula_sum 'C16 H34 Cl Cu N4 Na O11' _chemical_formula_weight 580.45 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' Na Na 0.0362 0.0249 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0242(5) _cell_length_b 9.3141(6) _cell_length_c 15.3597(10) _cell_angle_alpha 96.6070(10) _cell_angle_beta 97.3590(10) _cell_angle_gamma 92.5420(10) _cell_volume 1128.90(13) _cell_formula_units_Z 2 _cell_measurement_temperature 218(2) _cell_measurement_reflns_used 7119 _cell_measurement_theta_min 2.44 _cell_measurement_theta_max 28.26 _exptl_crystal_description BLOCKS _exptl_crystal_colour BLUE _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.708 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 1.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6514 _exptl_absorpt_correction_T_max 0.7826 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 218(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 8321 _diffrn_reflns_av_R_equivalents 0.0181 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 28.26 _reflns_number_total 5124 _reflns_number_gt 4894 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+0.7403P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5124 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0358 _refine_ls_wR_factor_ref 0.1011 _refine_ls_wR_factor_gt 0.1000 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 Na1 Na 0.05089(11) 1.20200(9) 0.50790(6) 0.02836(19) Uani 1 1 d . . . Cl1 Cl 0.80471(7) 1.66793(6) 1.11275(3) 0.03090(13) Uani 1 1 d . . . Cu1 Cu 0.61750(3) 0.83746(2) 0.720677(14) 0.01770(9) Uani 1 1 d . . . O1 O 0.6883(2) 0.76259(15) 0.60748(10) 0.0262(3) Uani 1 1 d . . . O2 O 0.7424(2) 0.60345(17) 0.50002(10) 0.0298(3) Uani 1 1 d . . . O3 O 0.35301(19) 0.86967(16) 0.63919(11) 0.0288(3) Uani 1 1 d . . . O4 O 0.16151(19) 0.98489(17) 0.56094(10) 0.0274(3) Uani 1 1 d . . . O5 O 0.0237(3) 1.3658(2) 0.64112(13) 0.0372(4) Uani 1 1 d . . . H5D H 0.059(5) 1.446(4) 0.632(2) 0.051(10) Uiso 1 1 d . . . H5C H 0.070(4) 1.361(3) 0.683(2) 0.035(9) Uiso 1 1 d . . . O6 O -0.1246(2) 1.3569(2) 0.42434(12) 0.0309(4) Uani 1 1 d . . . H6D H -0.193(4) 1.296(4) 0.402(2) 0.047(9) Uiso 1 1 d . . . H6C H -0.170(4) 1.410(3) 0.449(2) 0.032(8) Uiso 1 1 d . . . O7 O 0.7555(3) 1.6841(2) 1.19960(12) 0.0479(5) Uani 1 1 d . . . O8 O 0.9423(4) 1.5784(4) 1.1131(2) 0.0952(11) Uani 1 1 d . . . O9 O 0.6674(3) 1.6074(3) 1.05003(14) 0.0655(7) Uani 1 1 d . . . O10 O 0.8534(3) 1.8062(2) 1.09098(14) 0.0548(6) Uani 1 1 d . . . O11 O 1.2201(5) 1.6995(3) 1.01449(19) 0.0909(10) Uani 1 1 d . . . H11C H 1.1466 1.7800 1.0220 0.109 Uiso 1 1 calc R . . H11D H 1.3373 1.7202 1.0417 0.109 Uiso 1 1 calc R . . N1 N 0.5490(2) 0.91375(19) 0.83897(11) 0.0238(3) Uani 1 1 d . . . N2 N 0.6878(2) 1.04679(17) 0.70876(11) 0.0199(3) Uani 1 1 d . . . N3 N 0.8712(2) 0.84623(19) 0.79919(11) 0.0226(3) Uani 1 1 d . . . N4 N 0.5817(2) 0.64177(18) 0.76407(11) 0.0232(3) Uani 1 1 d . . . C1 C 0.5034(3) 1.0628(2) 0.82761(15) 0.0284(4) Uani 1 1 d . . . H1A H 0.4896 1.1157 0.8849 0.034 Uiso 1 1 calc R . . H1B H 0.3967 1.0608 0.7884 0.034 Uiso 1 1 calc R . . C2 C 0.6426(3) 1.1374(2) 0.78802(14) 0.0268(4) Uani 1 1 d . . . H2A H 0.6057 1.2304 0.7711 0.032 Uiso 1 1 calc R . . H2B H 0.7423 1.1568 0.8326 0.032 Uiso 1 1 calc R . . C3 C 0.8744(3) 1.0545(2) 0.70854(16) 0.0296(5) Uani 1 1 d . . . H3A H 0.9209 1.1469 0.7416 0.036 Uiso 1 1 calc R . . H3B H 0.8968 1.0549 0.6473 0.036 Uiso 1 1 calc R . . C4 C 0.9694(3) 0.9323(2) 0.74778(14) 0.0260(4) Uani 1 1 d . . . H4A H 1.0051 0.8679 0.6994 0.031 Uiso 1 1 calc R . . H4B H 1.0711 0.9747 0.7859 0.031 Uiso 1 1 calc R . . C5 C 0.8993(3) 0.6914(2) 0.79063(15) 0.0276(4) Uani 1 1 d . . . H5B H 0.9988 0.6743 0.8314 0.033 Uiso 1 1 calc R . . H5A H 0.9208 0.6593 0.7303 0.033 Uiso 1 1 calc R . . C6 C 0.7467(3) 0.6031(2) 0.81119(15) 0.0285(4) Uani 1 1 d . . . H6A H 0.7613 0.5001 0.7946 0.034 Uiso 1 1 calc R . . H6B H 0.7428 0.6180 0.8751 0.034 Uiso 1 1 calc R . . C7 C 0.4512(3) 0.6575(3) 0.82573(16) 0.0312(5) Uani 1 1 d . . . H7A H 0.4947 0.6243 0.8821 0.037 Uiso 1 1 calc R . . H7B H 0.3505 0.5960 0.8002 0.037 Uiso 1 1 calc R . . C8 C 0.4031(3) 0.8137(2) 0.84271(15) 0.0293(4) Uani 1 1 d . . . H8A H 0.3101 0.8315 0.7981 0.035 Uiso 1 1 calc R . . H8B H 0.3654 0.8307 0.9010 0.035 Uiso 1 1 calc R . . C9 C 0.6827(3) 0.9083(3) 0.91438(14) 0.0292(4) Uani 1 1 d . . . H9A H 0.6631 0.8194 0.9410 0.035 Uiso 1 1 calc R . . H9B H 0.6741 0.9905 0.9592 0.035 Uiso 1 1 calc R . . C10 C 0.8625(3) 0.9125(3) 0.88914(14) 0.0289(4) Uani 1 1 d . . . H10A H 0.9066 1.0135 0.8954 0.035 Uiso 1 1 calc R . . H10B H 0.9349 0.8620 0.9305 0.035 Uiso 1 1 calc R . . C11 C 0.6907(2) 0.6325(2) 0.57212(13) 0.0226(4) Uani 1 1 d . . . C12 C 0.6368(3) 0.5068(2) 0.61890(14) 0.0258(4) Uani 1 1 d . . . H12A H 0.5845 0.4298 0.5735 0.031 Uiso 1 1 calc R . . H12B H 0.7388 0.4695 0.6482 0.031 Uiso 1 1 calc R . . C13 C 0.5175(3) 0.5332(2) 0.68663(14) 0.0261(4) Uani 1 1 d . . . H13A H 0.4124 0.5656 0.6574 0.031 Uiso 1 1 calc R . . H13B H 0.4908 0.4411 0.7083 0.031 Uiso 1 1 calc R . . C14 C 0.3033(3) 0.9784(2) 0.60381(13) 0.0220(4) Uani 1 1 d . . . C15 C 0.4209(3) 1.1144(2) 0.61543(14) 0.0259(4) Uani 1 1 d . . . H15A H 0.3916 1.1670 0.5644 0.031 Uiso 1 1 calc R . . H15B H 0.3970 1.1761 0.6679 0.031 Uiso 1 1 calc R . . C16 C 0.6091(3) 1.0962(2) 0.62499(13) 0.0231(4) Uani 1 1 d . . . H16A H 0.6321 1.0267 0.5757 0.028 Uiso 1 1 calc R . . H16B H 0.6654 1.1893 0.6187 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.0269(4) 0.0252(4) 0.0324(4) 0.0081(3) -0.0024(3) 0.0015(3) Cl1 0.0361(3) 0.0280(3) 0.0292(3) 0.0088(2) 0.0018(2) 0.0030(2) Cu1 0.01884(14) 0.01447(13) 0.02018(13) 0.00487(8) 0.00169(9) 0.00074(9) O1 0.0371(8) 0.0165(7) 0.0258(7) 0.0042(5) 0.0055(6) 0.0013(6) O2 0.0323(8) 0.0245(8) 0.0320(8) -0.0013(6) 0.0067(6) 0.0018(6) O3 0.0266(8) 0.0200(7) 0.0383(8) 0.0097(6) -0.0059(6) -0.0007(6) O4 0.0226(7) 0.0263(8) 0.0326(8) 0.0083(6) -0.0034(6) 0.0019(6) O5 0.0410(10) 0.0379(11) 0.0332(9) 0.0105(8) 0.0031(8) -0.0008(8) O6 0.0285(8) 0.0236(8) 0.0380(9) 0.0013(7) -0.0033(7) 0.0028(7) O7 0.0578(12) 0.0556(12) 0.0333(9) 0.0129(8) 0.0099(8) 0.0051(10) O8 0.102(2) 0.108(2) 0.092(2) 0.0343(18) 0.0311(18) 0.076(2) O9 0.0833(17) 0.0607(14) 0.0430(11) 0.0110(10) -0.0176(11) -0.0370(13) O10 0.0661(14) 0.0476(12) 0.0485(11) 0.0218(9) -0.0054(10) -0.0232(10) O11 0.134(3) 0.0654(17) 0.0722(17) -0.0122(14) 0.0364(18) -0.0192(18) N1 0.0240(8) 0.0237(9) 0.0250(8) 0.0066(6) 0.0042(7) 0.0024(7) N2 0.0182(8) 0.0175(8) 0.0238(8) 0.0049(6) 0.0005(6) 0.0006(6) N3 0.0208(8) 0.0207(8) 0.0262(8) 0.0058(6) 0.0004(6) 0.0017(6) N4 0.0223(8) 0.0199(8) 0.0280(8) 0.0078(6) 0.0018(7) 0.0003(6) C1 0.0337(11) 0.0238(10) 0.0295(10) 0.0030(8) 0.0086(9) 0.0082(9) C2 0.0342(11) 0.0187(9) 0.0261(10) 0.0017(7) -0.0004(8) 0.0016(8) C3 0.0204(10) 0.0262(11) 0.0438(12) 0.0142(9) 0.0027(9) -0.0015(8) C4 0.0189(9) 0.0266(10) 0.0334(10) 0.0075(8) 0.0037(8) 0.0017(8) C5 0.0224(10) 0.0238(10) 0.0363(11) 0.0073(8) -0.0017(8) 0.0042(8) C6 0.0286(11) 0.0231(10) 0.0338(11) 0.0124(8) -0.0039(8) 0.0018(8) C7 0.0295(11) 0.0304(11) 0.0369(11) 0.0139(9) 0.0090(9) -0.0021(9) C8 0.0251(10) 0.0318(11) 0.0339(11) 0.0095(9) 0.0103(8) 0.0010(9) C9 0.0332(11) 0.0333(12) 0.0216(9) 0.0064(8) 0.0023(8) 0.0031(9) C10 0.0288(11) 0.0312(11) 0.0244(10) 0.0034(8) -0.0042(8) -0.0005(9) C11 0.0185(9) 0.0191(9) 0.0284(10) 0.0025(7) -0.0027(7) 0.0015(7) C12 0.0267(10) 0.0162(9) 0.0334(10) 0.0041(8) -0.0016(8) 0.0019(8) C13 0.0242(10) 0.0184(9) 0.0348(11) 0.0066(8) -0.0011(8) -0.0030(8) C14 0.0223(9) 0.0209(9) 0.0225(9) 0.0036(7) 0.0015(7) 0.0012(7) C15 0.0261(10) 0.0189(9) 0.0314(10) 0.0081(8) -0.0052(8) 0.0016(8) C16 0.0254(10) 0.0188(9) 0.0256(9) 0.0088(7) 0.0011(8) -0.0008(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Na1 O6 2.4198(19) . ? Na1 O2 2.4257(18) 2_676 ? Na1 O4 2.4278(17) . ? Na1 O4 2.4299(17) 2_576 ? Na1 O5 2.447(2) . ? Na1 O1 2.9418(18) 2_676 ? Na1 C11 2.999(2) 2_676 ? Na1 Na1 3.7884(17) 2_576 ? Cl1 O8 1.413(3) . ? Cl1 O9 1.417(2) . ? Cl1 O10 1.418(2) . ? Cl1 O7 1.4327(19) . ? Cu1 O1 1.9598(15) . ? Cu1 N1 2.0254(17) . ? Cu1 N4 2.0325(17) . ? Cu1 N2 2.0407(16) . ? Cu1 N3 2.2222(17) . ? Cu1 O3 2.3713(15) . ? O1 C11 1.272(2) . ? O1 Na1 2.9418(18) 2_676 ? O2 C11 1.237(3) . ? O2 Na1 2.4257(18) 2_676 ? O3 C14 1.260(3) . ? O4 C14 1.247(2) . ? O4 Na1 2.4299(17) 2_576 ? N1 C8 1.475(3) . ? N1 C1 1.475(3) . ? N1 C9 1.481(3) . ? N2 C16 1.490(2) . ? N2 C2 1.493(3) . ? N2 C3 1.496(3) . ? N3 C10 1.458(3) . ? N3 C4 1.462(3) . ? N3 C5 1.464(3) . ? N4 C13 1.491(3) . ? N4 C7 1.501(3) . ? N4 C6 1.504(3) . ? C1 C2 1.517(3) . ? C3 C4 1.535(3) . ? C5 C6 1.531(3) . ? C7 C8 1.524(3) . ? C9 C10 1.542(3) . ? C11 C12 1.517(3) . ? C11 Na1 2.999(2) 2_676 ? C12 C13 1.509(3) . ? C14 C15 1.524(3) . ? C15 C16 1.518(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Na1 O2 80.37(6) . 2_676 ? O6 Na1 O4 160.50(7) . . ? O2 Na1 O4 115.89(6) 2_676 . ? O6 Na1 O4 83.24(6) . 2_576 ? O2 Na1 O4 151.76(7) 2_676 2_576 ? O4 Na1 O4 77.50(6) . 2_576 ? O6 Na1 O5 87.97(7) . . ? O2 Na1 O5 78.18(6) 2_676 . ? O4 Na1 O5 105.30(7) . . ? O4 Na1 O5 124.14(7) 2_576 . ? O6 Na1 O1 89.53(6) . 2_676 ? O2 Na1 O1 46.91(5) 2_676 2_676 ? O4 Na1 O1 94.32(5) . 2_676 ? O4 Na1 O1 110.46(6) 2_576 2_676 ? O5 Na1 O1 124.55(6) . 2_676 ? O6 Na1 C11 78.89(6) . 2_676 ? O2 Na1 C11 23.46(5) 2_676 2_676 ? O4 Na1 C11 111.43(6) . 2_676 ? O4 Na1 C11 130.03(6) 2_576 2_676 ? O5 Na1 C11 101.52(7) . 2_676 ? O1 Na1 C11 24.70(5) 2_676 2_676 ? O6 Na1 Na1 121.91(6) . 2_576 ? O2 Na1 Na1 147.66(6) 2_676 2_576 ? O4 Na1 Na1 38.77(4) . 2_576 ? O4 Na1 Na1 38.73(4) 2_576 2_576 ? O5 Na1 Na1 121.94(6) . 2_576 ? O1 Na1 Na1 105.81(5) 2_676 2_576 ? C11 Na1 Na1 130.30(6) 2_676 2_576 ? O8 Cl1 O9 111.1(2) . . ? O8 Cl1 O10 109.8(2) . . ? O9 Cl1 O10 108.55(13) . . ? O8 Cl1 O7 108.33(16) . . ? O9 Cl1 O7 109.99(14) . . ? O10 Cl1 O7 109.01(13) . . ? O1 Cu1 N1 178.81(7) . . ? O1 Cu1 N4 96.31(7) . . ? N1 Cu1 N4 83.32(7) . . ? O1 Cu1 N2 93.42(6) . . ? N1 Cu1 N2 86.73(7) . . ? N4 Cu1 N2 165.21(7) . . ? O1 Cu1 N3 96.04(7) . . ? N1 Cu1 N3 82.80(7) . . ? N4 Cu1 N3 85.52(7) . . ? N2 Cu1 N3 82.39(6) . . ? O1 Cu1 O3 86.71(6) . . ? N1 Cu1 O3 94.47(7) . . ? N4 Cu1 O3 103.07(6) . . ? N2 Cu1 O3 88.57(6) . . ? N3 Cu1 O3 170.68(6) . . ? C11 O1 Cu1 129.63(14) . . ? C11 O1 Na1 80.15(12) . 2_676 ? Cu1 O1 Na1 143.18(7) . 2_676 ? C11 O2 Na1 105.22(13) . 2_676 ? C14 O3 Cu1 129.11(13) . . ? C14 O4 Na1 125.03(14) . . ? C14 O4 Na1 131.94(14) . 2_576 ? Na1 O4 Na1 102.50(6) . 2_576 ? C8 N1 C1 113.58(17) . . ? C8 N1 C9 111.76(17) . . ? C1 N1 C9 112.59(18) . . ? C8 N1 Cu1 100.93(13) . . ? C1 N1 Cu1 103.80(12) . . ? C9 N1 Cu1 113.40(13) . . ? C16 N2 C2 111.61(16) . . ? C16 N2 C3 107.74(16) . . ? C2 N2 C3 110.58(16) . . ? C16 N2 Cu1 113.16(12) . . ? C2 N2 Cu1 106.71(12) . . ? C3 N2 Cu1 106.97(12) . . ? C10 N3 C4 114.61(17) . . ? C10 N3 C5 114.95(17) . . ? C4 N3 C5 115.35(17) . . ? C10 N3 Cu1 109.32(13) . . ? C4 N3 Cu1 101.05(12) . . ? C5 N3 Cu1 99.07(12) . . ? C13 N4 C7 109.47(17) . . ? C13 N4 C6 112.08(16) . . ? C7 N4 C6 111.19(17) . . ? C13 N4 Cu1 108.71(12) . . ? C7 N4 Cu1 107.04(13) . . ? C6 N4 Cu1 108.17(12) . . ? N1 C1 C2 108.56(17) . . ? N2 C2 C1 111.50(17) . . ? N2 C3 C4 116.10(17) . . ? N3 C4 C3 114.13(17) . . ? N3 C5 C6 111.15(18) . . ? N4 C6 C5 113.72(17) . . ? N4 C7 C8 111.90(17) . . ? N1 C8 C7 110.04(18) . . ? N1 C9 C10 114.04(17) . . ? N3 C10 C9 113.28(17) . . ? O2 C11 O1 121.43(19) . . ? O2 C11 C12 117.56(18) . . ? O1 C11 C12 120.96(19) . . ? O2 C11 Na1 51.31(11) . 2_676 ? O1 C11 Na1 75.15(12) . 2_676 ? C12 C11 Na1 151.52(14) . 2_676 ? C13 C12 C11 118.58(17) . . ? N4 C13 C12 115.04(17) . . ? O4 C14 O3 124.62(19) . . ? O4 C14 C15 116.67(18) . . ? O3 C14 C15 118.69(18) . . ? C16 C15 C14 118.09(17) . . ? N2 C16 C15 117.03(17) . . ? 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 H5D O6 0.82(4) 2.19(4) 2.993(3) 167(3) 2_586 O5 H5C O7 0.70(3) 2.23(4) 2.927(3) 169(3) 2_687 O5 H5C O8 0.70(3) 3.14(3) 3.723(4) 143(3) 2_687 O5 H5C Cl1 0.70(3) 3.22(3) 3.907(2) 166(3) 2_687 O6 H6D O3 0.79(4) 1.96(4) 2.737(2) 171(3) 2_576 O6 H6D O4 0.79(4) 2.76(3) 3.221(2) 119(3) 2_576 O6 H6C O2 0.73(3) 2.07(3) 2.772(2) 163(3) 1_465 O11 H11C O10 0.98 2.71 3.450(4) 132.6 . O11 H11D O9 0.98 2.89 3.714(5) 142.8 1_655 _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.627 _refine_diff_density_min -0.567 _refine_diff_density_rms 0.078 #===END #===END data_wong117 _database_code_depnum_ccdc_archive 'CCDC 635720' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H37 Cl Cu N4 O9' _chemical_formula_weight 564.52 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 Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 27.6657(19) _cell_length_b 7.9539(6) _cell_length_c 10.7296(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2361.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 8369 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 28.20 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1188 _exptl_absorpt_coefficient_mu 1.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.819 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 15470 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.40 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4274 _reflns_number_gt 4095 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0363P)^2^+0.2591P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.040(9) _refine_ls_number_reflns 4274 _refine_ls_number_parameters 316 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0246 _refine_ls_wR_factor_ref 0.0614 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.002 _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 0.616167(8) 0.90361(3) 0.55839(3) 0.01981(7) Uani 1 1 d . . . Cl1A Cl 0.68855(2) 0.44676(8) 0.00650(5) 0.03482(14) Uani 1 1 d . . . O1 O 0.58991(5) 1.13426(17) 0.54578(16) 0.0252(3) Uani 1 1 d . . . O2 O 0.53753(6) 1.2768(2) 0.43027(15) 0.0345(4) Uani 1 1 d . . . O3 O 0.55016(6) 0.8202(2) 0.40870(15) 0.0334(4) Uani 1 1 d . . . O4 O 0.48583(7) 0.6608(2) 0.36759(18) 0.0349(4) Uani 1 1 d . . . H4 H 0.4951(12) 0.665(4) 0.304(3) 0.049(10) Uiso 1 1 d . . . N1 N 0.66514(7) 0.9457(3) 0.41621(18) 0.0233(4) Uani 1 1 d . . . N2 N 0.67765(7) 0.9502(3) 0.68598(18) 0.0256(4) Uani 1 1 d . . . N3 N 0.56764(7) 0.8614(2) 0.70074(17) 0.0234(4) Uani 1 1 d . . . N4 N 0.63513(7) 0.6530(2) 0.57656(17) 0.0238(4) Uani 1 1 d . . . C1 C 0.57466(8) 1.1898(3) 0.4411(2) 0.0251(5) Uani 1 1 d . . . C2 C 0.60411(9) 1.1515(3) 0.3262(2) 0.0280(5) Uani 1 1 d . . . H2A H 0.6027 1.2484 0.2700 0.034 Uiso 1 1 calc R . . H2B H 0.5895 1.0555 0.2830 0.034 Uiso 1 1 calc R . . C3 C 0.65668(9) 1.1116(3) 0.3534(2) 0.0271(5) Uani 1 1 d . . . H3A H 0.6746 1.1130 0.2747 0.033 Uiso 1 1 calc R . . H3B H 0.6699 1.2008 0.4063 0.033 Uiso 1 1 calc R . . C4 C 0.71445(8) 0.9537(3) 0.4747(2) 0.0286(5) Uani 1 1 d . . . H4A H 0.7361 1.0191 0.4211 0.034 Uiso 1 1 calc R . . H4B H 0.7277 0.8398 0.4819 0.034 Uiso 1 1 calc R . . C5 C 0.71229(9) 1.0340(3) 0.6027(2) 0.0321(5) Uani 1 1 d . . . H5A H 0.7445 1.0301 0.6405 0.039 Uiso 1 1 calc R . . H5B H 0.7031 1.1524 0.5937 0.039 Uiso 1 1 calc R . . C6 C 0.66394(10) 1.0646(4) 0.7878(2) 0.0330(6) Uani 1 1 d . . . H6A H 0.6553 1.1738 0.7518 0.040 Uiso 1 1 calc R . . H6B H 0.6921 1.0818 0.8416 0.040 Uiso 1 1 calc R . . C7 C 0.62202(10) 1.0039(3) 0.8678(2) 0.0348(6) Uani 1 1 d . . . H7A H 0.6305 0.8936 0.9021 0.042 Uiso 1 1 calc R . . H7B H 0.6184 1.0815 0.9381 0.042 Uiso 1 1 calc R . . C8 C 0.57360(9) 0.9884(3) 0.8031(2) 0.0296(5) Uani 1 1 d . . . H8A H 0.5494 0.9634 0.8671 0.036 Uiso 1 1 calc R . . H8B H 0.5656 1.0989 0.7684 0.036 Uiso 1 1 calc R . . C9 C 0.51621(8) 0.8869(3) 0.6588(2) 0.0289(5) Uani 1 1 d . . . H9A H 0.5144 0.9966 0.6176 0.035 Uiso 1 1 calc R . . H9B H 0.4960 0.8935 0.7337 0.035 Uiso 1 1 calc R . . C10 C 0.49363(7) 0.7591(3) 0.5726(2) 0.0296(5) Uani 1 1 d . . . H10A H 0.4974 0.6477 0.6104 0.035 Uiso 1 1 calc R . . H10B H 0.4589 0.7826 0.5676 0.035 Uiso 1 1 calc R . . C11 C 0.51328(8) 0.7516(3) 0.4423(2) 0.0272(5) Uani 1 1 d . . . C12 C 0.57614(9) 0.6886(3) 0.7493(2) 0.0271(5) Uani 1 1 d . . . H12A H 0.5459 0.6436 0.7834 0.032 Uiso 1 1 calc R . . H12B H 0.5999 0.6929 0.8169 0.032 Uiso 1 1 calc R . . C13 C 0.59432(9) 0.5738(3) 0.6471(2) 0.0274(5) Uani 1 1 d . . . H13A H 0.6053 0.4677 0.6838 0.033 Uiso 1 1 calc R . . H13B H 0.5678 0.5486 0.5895 0.033 Uiso 1 1 calc R . . C14 C 0.63859(10) 0.5621(3) 0.4547(2) 0.0288(5) Uani 1 1 d . . . H14A H 0.6064 0.5601 0.4165 0.035 Uiso 1 1 calc R . . H14B H 0.6479 0.4454 0.4714 0.035 Uiso 1 1 calc R . . C15 C 0.67381(10) 0.6347(3) 0.3611(2) 0.0318(5) Uani 1 1 d . . . H15A H 0.6743 0.5614 0.2877 0.038 Uiso 1 1 calc R . . H15B H 0.7062 0.6324 0.3979 0.038 Uiso 1 1 calc R . . C16 C 0.66323(8) 0.8124(3) 0.3185(2) 0.0278(5) Uani 1 1 d . . . H16A H 0.6864 0.8418 0.2530 0.033 Uiso 1 1 calc R . . H16B H 0.6309 0.8140 0.2810 0.033 Uiso 1 1 calc R . . C17 C 0.68206(9) 0.6378(3) 0.6446(2) 0.0288(5) Uani 1 1 d . . . H17A H 0.7081 0.6264 0.5831 0.035 Uiso 1 1 calc R . . H17B H 0.6814 0.5342 0.6941 0.035 Uiso 1 1 calc R . . C18 C 0.69420(8) 0.7841(3) 0.7308(2) 0.0299(5) Uani 1 1 d . . . H18A H 0.6796 0.7627 0.8125 0.036 Uiso 1 1 calc R . . H18B H 0.7293 0.7881 0.7423 0.036 Uiso 1 1 calc R . . O1A O 0.69718(8) 0.6171(2) 0.0435(2) 0.0569(6) Uani 1 1 d . . . O2A O 0.65208(10) 0.4440(3) -0.0878(2) 0.0647(6) Uani 1 1 d . . . O3A O 0.67240(13) 0.3519(3) 0.1091(2) 0.0845(9) Uani 1 1 d . . . O4A O 0.73158(9) 0.3770(3) -0.0434(3) 0.0788(9) Uani 1 1 d . . . O1S O 0.51232(7) 0.6574(3) 0.13632(17) 0.0390(4) Uani 1 1 d . . . H1S H 0.4959(11) 0.681(4) 0.084(3) 0.042(9) Uiso 1 1 d . . . C1S C 0.56162(10) 0.6523(4) 0.1023(3) 0.0461(7) Uani 1 1 d . . . H1SA H 0.5655 0.5835 0.0284 0.069 Uiso 1 1 calc R . . H1SB H 0.5803 0.6046 0.1701 0.069 Uiso 1 1 calc R . . H1SC H 0.5729 0.7654 0.0852 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01818(12) 0.01936(12) 0.02189(11) 0.00006(12) 0.00149(12) 0.00055(9) Cl1A 0.0438(4) 0.0318(3) 0.0288(2) 0.0015(3) -0.0007(3) -0.0057(3) O1 0.0292(8) 0.0214(7) 0.0250(8) 0.0017(7) 0.0011(7) 0.0049(6) O2 0.0292(9) 0.0422(10) 0.0322(8) 0.0020(8) 0.0002(7) 0.0139(8) O3 0.0287(9) 0.0419(10) 0.0294(8) -0.0011(7) 0.0010(7) -0.0108(8) O4 0.0321(10) 0.0375(10) 0.0352(10) -0.0007(8) -0.0042(8) -0.0067(8) N1 0.0182(9) 0.0240(9) 0.0276(9) 0.0001(8) 0.0007(8) 0.0010(8) N2 0.0233(10) 0.0252(10) 0.0284(10) -0.0035(8) -0.0056(8) -0.0005(9) N3 0.0211(10) 0.0238(9) 0.0252(9) 0.0020(8) 0.0010(8) 0.0012(8) N4 0.0247(9) 0.0209(8) 0.0257(10) -0.0024(8) 0.0011(8) 0.0000(7) C1 0.0225(11) 0.0212(11) 0.0317(11) 0.0008(9) -0.0003(9) -0.0032(9) C2 0.0287(12) 0.0270(12) 0.0283(10) 0.0047(9) 0.0010(10) 0.0026(10) C3 0.0234(12) 0.0251(12) 0.0330(12) 0.0049(9) 0.0041(10) -0.0013(9) C4 0.0159(11) 0.0335(13) 0.0363(12) 0.0007(10) 0.0021(9) 0.0002(10) C5 0.0219(11) 0.0338(13) 0.0406(12) -0.0001(10) -0.0062(9) -0.0032(10) C6 0.0293(14) 0.0348(14) 0.0348(12) -0.0086(11) -0.0075(11) 0.0026(12) C7 0.0419(14) 0.0345(14) 0.0281(12) -0.0065(10) -0.0026(10) 0.0027(11) C8 0.0328(13) 0.0296(12) 0.0264(11) -0.0034(9) 0.0055(10) 0.0063(11) C9 0.0228(12) 0.0331(13) 0.0308(11) 0.0030(10) 0.0066(9) 0.0032(10) C10 0.0175(9) 0.0347(11) 0.0365(13) 0.0074(11) 0.0004(10) -0.0035(8) C11 0.0247(12) 0.0252(12) 0.0317(11) 0.0036(10) -0.0048(9) 0.0022(10) C12 0.0266(12) 0.0271(12) 0.0275(10) 0.0051(9) 0.0016(9) -0.0017(10) C13 0.0284(12) 0.0217(11) 0.0321(11) 0.0037(9) 0.0032(10) -0.0018(9) C14 0.0342(14) 0.0202(11) 0.0321(12) -0.0061(9) 0.0022(10) 0.0005(10) C15 0.0335(13) 0.0290(12) 0.0328(12) -0.0075(10) 0.0081(10) 0.0043(11) C16 0.0245(12) 0.0333(13) 0.0254(10) -0.0041(10) 0.0052(9) -0.0005(10) C17 0.0270(13) 0.0265(12) 0.0331(11) 0.0008(10) -0.0015(10) 0.0065(10) C18 0.0233(12) 0.0333(13) 0.0332(11) 0.0025(10) -0.0064(9) 0.0039(10) O1A 0.0802(15) 0.0380(10) 0.0526(13) -0.0060(10) 0.0001(13) -0.0128(10) O2A 0.0738(16) 0.0634(14) 0.0569(13) -0.0004(12) -0.0240(13) 0.0040(12) O3A 0.141(3) 0.0667(16) 0.0456(12) 0.0195(12) 0.0047(15) -0.0296(17) O4A 0.0509(15) 0.0670(16) 0.119(2) -0.0315(16) 0.0086(15) 0.0009(12) O1S 0.0365(11) 0.0501(12) 0.0303(9) -0.0011(8) -0.0050(9) 0.0043(9) C1S 0.0370(15) 0.0634(18) 0.0380(13) 0.0034(13) -0.0061(11) -0.0111(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 Cu1 O1 1.9778(14) . ? Cu1 N3 2.0611(19) . ? Cu1 N1 2.068(2) . ? Cu1 N4 2.0705(18) . ? Cu1 N2 2.2147(19) . ? Cu1 O3 2.5207(17) . ? Cl1A O3A 1.408(2) . ? Cl1A O4A 1.418(3) . ? Cl1A O2A 1.429(2) . ? Cl1A O1A 1.432(2) . ? O1 C1 1.278(3) . ? O2 C1 1.244(3) . ? O3 C11 1.212(3) . ? O4 C11 1.319(3) . ? O4 H4 0.73(3) . ? N1 C16 1.491(3) . ? N1 C3 1.500(3) . ? N1 C4 1.503(3) . ? N2 C5 1.470(3) . ? N2 C6 1.471(3) . ? N2 C18 1.478(3) . ? N3 C12 1.488(3) . ? N3 C8 1.501(3) . ? N3 C9 1.506(3) . ? N4 C17 1.494(3) . ? N4 C14 1.497(3) . ? N4 C13 1.498(3) . ? C1 C2 1.508(3) . ? C2 C3 1.517(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.515(3) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C7 1.521(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.514(3) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 C10 1.509(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.502(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C12 C13 1.514(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.513(3) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 C16 1.514(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C17 C18 1.524(3) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? O1S C1S 1.412(3) . ? O1S H1S 0.75(3) . ? C1S H1SA 0.9700 . ? C1S H1SB 0.9700 . ? C1S H1SC 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N3 87.86(7) . . ? O1 Cu1 N1 92.30(7) . . ? N3 Cu1 N1 179.70(8) . . ? O1 Cu1 N4 173.01(7) . . ? N3 Cu1 N4 86.47(7) . . ? N1 Cu1 N4 93.39(8) . . ? O1 Cu1 N2 99.75(8) . . ? N3 Cu1 N2 93.99(7) . . ? N1 Cu1 N2 85.74(7) . . ? N4 Cu1 N2 84.73(8) . . ? O1 Cu1 O3 86.24(6) . . ? N3 Cu1 O3 87.56(6) . . ? N1 Cu1 O3 92.70(7) . . ? N4 Cu1 O3 89.44(7) . . ? N2 Cu1 O3 173.86(7) . . ? O3A Cl1A O4A 110.6(2) . . ? O3A Cl1A O2A 108.75(17) . . ? O4A Cl1A O2A 108.64(17) . . ? O3A Cl1A O1A 110.05(15) . . ? O4A Cl1A O1A 109.57(15) . . ? O2A Cl1A O1A 109.19(15) . . ? C1 O1 Cu1 120.11(14) . . ? C11 O3 Cu1 122.63(15) . . ? C11 O4 H4 110(3) . . ? C16 N1 C3 107.67(19) . . ? C16 N1 C4 110.85(18) . . ? C3 N1 C4 106.98(19) . . ? C16 N1 Cu1 112.35(14) . . ? C3 N1 Cu1 111.81(15) . . ? C4 N1 Cu1 107.07(14) . . ? C5 N2 C6 109.8(2) . . ? C5 N2 C18 113.65(19) . . ? C6 N2 C18 113.02(19) . . ? C5 N2 Cu1 101.57(14) . . ? C6 N2 Cu1 111.35(15) . . ? C18 N2 Cu1 106.84(14) . . ? C12 N3 C8 110.33(17) . . ? C12 N3 C9 112.21(18) . . ? C8 N3 C9 103.39(17) . . ? C12 N3 Cu1 107.89(14) . . ? C8 N3 Cu1 111.16(14) . . ? C9 N3 Cu1 111.86(13) . . ? C17 N4 C14 109.38(17) . . ? C17 N4 C13 111.96(18) . . ? C14 N4 C13 106.66(17) . . ? C17 N4 Cu1 110.12(13) . . ? C14 N4 Cu1 113.50(14) . . ? C13 N4 Cu1 105.15(13) . . ? O2 C1 O1 123.1(2) . . ? O2 C1 C2 118.8(2) . . ? O1 C1 C2 118.02(19) . . ? C1 C2 C3 113.8(2) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? N1 C3 C2 114.84(19) . . ? N1 C3 H3A 108.6 . . ? C2 C3 H3A 108.6 . . ? N1 C3 H3B 108.6 . . ? C2 C3 H3B 108.6 . . ? H3A C3 H3B 107.5 . . ? N1 C4 C5 111.13(19) . . ? N1 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N1 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N2 C5 C4 112.68(19) . . ? N2 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? N2 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? N2 C6 C7 114.8(2) . . ? N2 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N2 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? C8 C7 C6 116.2(2) . . ? C8 C7 H7A 108.2 . . ? C6 C7 H7A 108.2 . . ? C8 C7 H7B 108.2 . . ? C6 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? N3 C8 C7 119.17(19) . . ? N3 C8 H8A 107.5 . . ? C7 C8 H8A 107.5 . . ? N3 C8 H8B 107.5 . . ? C7 C8 H8B 107.5 . . ? H8A C8 H8B 107.0 . . ? N3 C9 C10 118.91(19) . . ? N3 C9 H9A 107.6 . . ? C10 C9 H9A 107.6 . . ? N3 C9 H9B 107.6 . . ? C10 C9 H9B 107.6 . . ? H9A C9 H9B 107.0 . . ? C11 C10 C9 116.61(19) . . ? C11 C10 H10A 108.1 . . ? C9 C10 H10A 108.1 . . ? C11 C10 H10B 108.1 . . ? C9 C10 H10B 108.1 . . ? H10A C10 H10B 107.3 . . ? O3 C11 O4 123.4(2) . . ? O3 C11 C10 124.3(2) . . ? O4 C11 C10 112.3(2) . . ? N3 C12 C13 110.83(18) . . ? N3 C12 H12A 109.5 . . ? C13 C12 H12A 109.5 . . ? N3 C12 H12B 109.5 . . ? C13 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? N4 C13 C12 111.30(18) . . ? N4 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? N4 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? N4 C14 C15 115.88(19) . . ? N4 C14 H14A 108.3 . . ? C15 C14 H14A 108.3 . . ? N4 C14 H14B 108.3 . . ? C15 C14 H14B 108.3 . . ? H14A C14 H14B 107.4 . . ? C14 C15 C16 115.6(2) . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15B 108.4 . . ? C16 C15 H15B 108.4 . . ? H15A C15 H15B 107.4 . . ? N1 C16 C15 116.38(19) . . ? N1 C16 H16A 108.2 . . ? C15 C16 H16A 108.2 . . ? N1 C16 H16B 108.2 . . ? C15 C16 H16B 108.2 . . ? H16A C16 H16B 107.3 . . ? N4 C17 C18 115.21(18) . . ? N4 C17 H17A 108.5 . . ? C18 C17 H17A 108.5 . . ? N4 C17 H17B 108.5 . . ? C18 C17 H17B 108.5 . . ? H17A C17 H17B 107.5 . . ? N2 C18 C17 114.62(18) . . ? N2 C18 H18A 108.6 . . ? C17 C18 H18A 108.6 . . ? N2 C18 H18B 108.6 . . ? C17 C18 H18B 108.6 . . ? H18A C18 H18B 107.6 . . ? C1S O1S H1S 113(2) . . ? O1S C1S H1SA 109.5 . . ? O1S C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? O1S C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? 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 O1S H1S O2 0.75(3) 1.92(3) 2.658(2) 170(3) 2_674 O4 H4 O1S 0.73(3) 1.86(3) 2.588(3) 173(4) . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.289 _refine_diff_density_min -0.207 _refine_diff_density_rms 0.048 #===END data_wong118 _database_code_depnum_ccdc_archive 'CCDC 635721' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H38 Cl2 Cu N4 O14' _chemical_formula_weight 668.96 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' 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.7623(5) _cell_length_b 17.9633(10) _cell_length_c 17.2184(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.2180(10) _cell_angle_gamma 90.00 _cell_volume 2705.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 4711 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 25.13 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1396 _exptl_absorpt_coefficient_mu 1.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.785 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_number 18531 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.00 _reflns_number_total 5315 _reflns_number_gt 4288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0568P)^2^+1.6685P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5315 _refine_ls_number_parameters 376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.1075 _refine_ls_wR_factor_gt 0.1005 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.13571(4) 0.246816(16) 0.458090(18) 0.02854(11) Uani 1 1 d . . . O1 O 0.0233(2) 0.21683(11) 0.55331(12) 0.0418(5) Uani 1 1 d . . . O2 O 0.0186(3) 0.20995(14) 0.68107(13) 0.0504(6) Uani 1 1 d . . . H2 H -0.013(4) 0.172(2) 0.673(2) 0.058(13) Uiso 1 1 d . . . O3 O 0.3661(3) 0.22493(12) 0.54596(12) 0.0460(5) Uani 1 1 d . . . O4 O 0.5956(3) 0.17264(17) 0.55879(18) 0.0639(7) Uani 1 1 d . . . H4 H 0.609(6) 0.213(3) 0.573(3) 0.085(17) Uiso 1 1 d . . . N1 N 0.1431(3) 0.13504(12) 0.43079(14) 0.0384(6) Uani 1 1 d . . . N2 N -0.0588(3) 0.27051(14) 0.37497(15) 0.0395(6) Uani 1 1 d . . . N3 N 0.2696(3) 0.26461(12) 0.36491(13) 0.0303(5) Uani 1 1 d . . . N4 N 0.1256(3) 0.35862(12) 0.48602(13) 0.0314(5) Uani 1 1 d . . . C1 C 0.4484(4) 0.17139(17) 0.53889(17) 0.0437(7) Uani 1 1 d . . . C2 C 0.3971(4) 0.09819(16) 0.50598(19) 0.0488(8) Uani 1 1 d . . . H2A H 0.4357 0.0589 0.5413 0.059 Uiso 1 1 calc R . . H2B H 0.4445 0.0910 0.4563 0.059 Uiso 1 1 calc R . . C3 C 0.2269(4) 0.08829(16) 0.49250(18) 0.0487(8) Uani 1 1 d . . . H3A H 0.1803 0.0979 0.5419 0.058 Uiso 1 1 calc R . . H3B H 0.2079 0.0359 0.4795 0.058 Uiso 1 1 calc R . . C4 C 0.2164(4) 0.12886(15) 0.35526(17) 0.0385(7) Uani 1 1 d . . . H4A H 0.1378 0.1318 0.3126 0.046 Uiso 1 1 calc R . . H4B H 0.2670 0.0804 0.3522 0.046 Uiso 1 1 calc R . . C5 C 0.3322(3) 0.18984(15) 0.34626(16) 0.0351(6) Uani 1 1 d . . . H5A H 0.4225 0.1798 0.3808 0.042 Uiso 1 1 calc R . . H5B H 0.3644 0.1900 0.2927 0.042 Uiso 1 1 calc R . . C6 C 0.4020(3) 0.31600(16) 0.38307(17) 0.0368(6) Uani 1 1 d . . . H6A H 0.4590 0.3216 0.3361 0.044 Uiso 1 1 calc R . . H6B H 0.4704 0.2925 0.4228 0.044 Uiso 1 1 calc R . . C7 C 0.3605(3) 0.39254(16) 0.41140(17) 0.0391(7) Uani 1 1 d . . . H7A H 0.2955 0.4167 0.3706 0.047 Uiso 1 1 calc R . . H7B H 0.4545 0.4219 0.4182 0.047 Uiso 1 1 calc R . . C8 C 0.2784(3) 0.39554(15) 0.48690(17) 0.0376(6) Uani 1 1 d . . . H8A H 0.3445 0.3725 0.5280 0.045 Uiso 1 1 calc R . . H8B H 0.2655 0.4479 0.5010 0.045 Uiso 1 1 calc R . . C9 C 0.0616(3) 0.37145(15) 0.56313(16) 0.0380(7) Uani 1 1 d . . . H9A H -0.0498 0.3667 0.5571 0.046 Uiso 1 1 calc R . . H9B H 0.0845 0.4228 0.5791 0.046 Uiso 1 1 calc R . . C10 C 0.1198(4) 0.31951(15) 0.62842(16) 0.0390(7) Uani 1 1 d . . . H10A H 0.2314 0.3157 0.6284 0.047 Uiso 1 1 calc R . . H10B H 0.0934 0.3400 0.6787 0.047 Uiso 1 1 calc R . . C11 C 0.0510(4) 0.24437(15) 0.61797(17) 0.0374(7) Uani 1 1 d . . . C12 C 0.0175(3) 0.39440(16) 0.42681(18) 0.0413(7) Uani 1 1 d . . . H12A H 0.0732 0.4080 0.3811 0.050 Uiso 1 1 calc R . . H12B H -0.0234 0.4402 0.4486 0.050 Uiso 1 1 calc R . . C13 C -0.1138(4) 0.34310(18) 0.40203(19) 0.0468(8) Uani 1 1 d . . . H13A H -0.1781 0.3353 0.4460 0.056 Uiso 1 1 calc R . . H13B H -0.1766 0.3667 0.3601 0.056 Uiso 1 1 calc R . . C14 C -0.1824(4) 0.2143(2) 0.3781(2) 0.0551(9) Uani 1 1 d . . . H14A H -0.2632 0.2268 0.3385 0.066 Uiso 1 1 calc R . . H14B H -0.2267 0.2174 0.4290 0.066 Uiso 1 1 calc R . . C15 C -0.1313(4) 0.13525(19) 0.3651(2) 0.0572(9) Uani 1 1 d . . . H15A H -0.0874 0.1328 0.3141 0.069 Uiso 1 1 calc R . . H15B H -0.2221 0.1033 0.3629 0.069 Uiso 1 1 calc R . . C16 C -0.0156(4) 0.10259(17) 0.4249(2) 0.0518(9) Uani 1 1 d . . . H16A H -0.0582 0.1070 0.4761 0.062 Uiso 1 1 calc R . . H16B H -0.0063 0.0493 0.4138 0.062 Uiso 1 1 calc R . . C17 C 0.1732(3) 0.29487(16) 0.29823(16) 0.0370(6) Uani 1 1 d . . . H17A H 0.2146 0.2771 0.2499 0.044 Uiso 1 1 calc R . . H17B H 0.1819 0.3493 0.2988 0.044 Uiso 1 1 calc R . . C18 C 0.0037(4) 0.27428(18) 0.29709(17) 0.0422(7) Uani 1 1 d . . . H18A H -0.0548 0.3111 0.2658 0.051 Uiso 1 1 calc R . . H18B H -0.0107 0.2258 0.2716 0.051 Uiso 1 1 calc R . . Cl1 Cl 0.65813(8) 0.37445(4) 0.62329(4) 0.04024(18) Uani 1 1 d . . . O5 O 0.6429(3) 0.40327(17) 0.54757(15) 0.0730(8) Uani 1 1 d . . . O6 O 0.7629(3) 0.41872(19) 0.66928(16) 0.0822(9) Uani 1 1 d . . . O7 O 0.5122(3) 0.37314(14) 0.65750(13) 0.0561(6) Uani 1 1 d . . . O8 O 0.7164(3) 0.30060(14) 0.62194(19) 0.0776(8) Uani 1 1 d . . . Cl2 Cl 0.44426(9) 0.01588(4) 0.71171(4) 0.04151(18) Uani 1 1 d . . . O9 O 0.4544(3) -0.04129(17) 0.6572(2) 0.0898(11) Uani 1 1 d . . . O10 O 0.3982(3) -0.01018(17) 0.78396(16) 0.0775(8) Uani 1 1 d . . . O11 O 0.5900(3) 0.05012(14) 0.72176(17) 0.0717(8) Uani 1 1 d . . . O12 O 0.3326(3) 0.06872(19) 0.68405(16) 0.0853(10) Uani 1 1 d . . . O1S O 0.4408(5) 0.5182(2) 0.7201(3) 0.0922(13) Uani 1 1 d . . . H1SA H 0.457(6) 0.477(3) 0.703(3) 0.086(17) Uiso 1 1 d . . . H1SB H 0.372(7) 0.517(3) 0.733(4) 0.11(2) Uiso 1 1 d . . . O2S O 0.8929(5) 0.08159(17) 0.6616(2) 0.0744(9) Uani 1 1 d . . . H2SA H 0.796(6) 0.075(3) 0.668(3) 0.086(17) Uiso 1 1 d . . . H2SB H 0.945(5) 0.066(2) 0.698(2) 0.052(14) 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 Cu1 0.0345(2) 0.02770(17) 0.02406(18) -0.00188(12) 0.00749(13) -0.00141(13) O1 0.0556(13) 0.0387(10) 0.0327(11) -0.0064(9) 0.0167(9) -0.0103(9) O2 0.0758(18) 0.0416(13) 0.0354(13) 0.0006(10) 0.0171(11) -0.0021(12) O3 0.0552(14) 0.0392(11) 0.0432(13) -0.0035(9) 0.0002(10) 0.0104(10) O4 0.0574(17) 0.0586(17) 0.0755(19) -0.0026(14) -0.0002(13) 0.0183(13) N1 0.0522(16) 0.0323(12) 0.0317(13) -0.0055(10) 0.0114(11) -0.0060(10) N2 0.0319(13) 0.0484(13) 0.0382(14) -0.0082(11) 0.0027(11) 0.0012(10) N3 0.0329(13) 0.0345(11) 0.0236(11) 0.0019(9) 0.0032(9) 0.0014(9) N4 0.0346(13) 0.0309(11) 0.0290(12) -0.0014(9) 0.0038(9) 0.0015(9) C1 0.058(2) 0.0440(16) 0.0293(16) 0.0074(13) 0.0082(14) 0.0146(15) C2 0.075(2) 0.0375(15) 0.0342(17) 0.0060(13) 0.0056(16) 0.0185(15) C3 0.083(3) 0.0277(14) 0.0367(17) 0.0023(12) 0.0110(16) -0.0014(14) C4 0.0492(18) 0.0362(14) 0.0308(15) -0.0056(12) 0.0084(13) 0.0035(12) C5 0.0396(16) 0.0404(15) 0.0259(14) -0.0027(11) 0.0066(12) 0.0073(12) C6 0.0339(15) 0.0450(15) 0.0320(15) 0.0045(12) 0.0071(12) -0.0047(12) C7 0.0428(17) 0.0402(15) 0.0346(16) 0.0043(12) 0.0048(13) -0.0094(12) C8 0.0433(17) 0.0337(14) 0.0360(16) -0.0023(12) 0.0023(13) -0.0058(12) C9 0.0449(17) 0.0340(14) 0.0358(16) -0.0071(12) 0.0083(13) 0.0024(12) C10 0.0474(18) 0.0416(15) 0.0290(15) -0.0081(12) 0.0108(13) -0.0021(13) C11 0.0429(17) 0.0403(15) 0.0304(15) -0.0012(12) 0.0141(13) 0.0033(12) C12 0.0455(18) 0.0365(15) 0.0416(17) 0.0000(13) -0.0008(14) 0.0122(13) C13 0.0375(17) 0.0580(19) 0.0445(18) -0.0089(15) -0.0020(14) 0.0144(14) C14 0.0338(18) 0.074(2) 0.057(2) -0.0203(18) 0.0056(15) -0.0110(16) C15 0.050(2) 0.062(2) 0.061(2) -0.0246(18) 0.0144(17) -0.0258(17) C16 0.064(2) 0.0429(17) 0.051(2) -0.0134(15) 0.0185(17) -0.0209(16) C17 0.0415(16) 0.0443(15) 0.0252(14) 0.0033(12) 0.0017(12) 0.0031(13) C18 0.0430(18) 0.0547(17) 0.0282(15) -0.0045(13) -0.0051(13) 0.0055(14) Cl1 0.0367(4) 0.0527(4) 0.0314(4) 0.0002(3) 0.0023(3) -0.0023(3) O5 0.0579(16) 0.112(2) 0.0501(15) 0.0308(15) 0.0101(12) 0.0114(15) O6 0.0561(17) 0.124(2) 0.0665(18) -0.0314(17) 0.0034(14) -0.0291(16) O7 0.0433(13) 0.0807(16) 0.0453(13) -0.0060(12) 0.0114(10) -0.0078(11) O8 0.0591(17) 0.0577(15) 0.116(3) 0.0064(15) 0.0087(16) 0.0072(12) Cl2 0.0421(4) 0.0480(4) 0.0345(4) -0.0054(3) 0.0022(3) -0.0021(3) O9 0.0529(16) 0.099(2) 0.118(3) -0.073(2) 0.0133(16) -0.0142(15) O10 0.0770(19) 0.098(2) 0.0588(17) 0.0304(15) 0.0141(14) 0.0068(16) O11 0.0615(16) 0.0632(16) 0.091(2) -0.0108(14) 0.0070(14) -0.0233(13) O12 0.0749(19) 0.124(3) 0.0573(17) 0.0229(17) 0.0093(14) 0.0444(18) O1S 0.080(3) 0.077(2) 0.126(3) -0.003(2) 0.059(2) 0.0018(19) O2S 0.079(2) 0.0579(17) 0.089(3) -0.0092(17) 0.030(2) -0.0108(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 Cu1 O1 2.0323(19) . ? Cu1 N1 2.064(2) . ? Cu1 N3 2.065(2) . ? Cu1 N4 2.068(2) . ? Cu1 N2 2.204(3) . ? Cu1 O3 2.485(2) . ? O1 C11 1.230(3) . ? O2 C11 1.295(4) . ? O2 H2 0.74(4) . ? O3 C1 1.212(4) . ? O4 C1 1.317(4) . ? O4 H4 0.77(5) . ? N1 C4 1.487(4) . ? N1 C16 1.506(4) . ? N1 C3 1.512(4) . ? N2 C13 1.475(4) . ? N2 C18 1.478(4) . ? N2 C14 1.484(4) . ? N3 C17 1.489(3) . ? N3 C5 1.493(3) . ? N3 C6 1.502(3) . ? N4 C9 1.488(4) . ? N4 C8 1.494(4) . ? N4 C12 1.497(4) . ? C1 C2 1.491(4) . ? C2 C3 1.507(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C4 C5 1.507(4) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C7 1.510(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.521(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 C10 1.526(4) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C10 C11 1.485(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C12 C13 1.516(4) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C14 C15 1.510(5) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C15 C16 1.521(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C17 C18 1.530(4) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? Cl1 O5 1.402(2) . ? Cl1 O6 1.422(3) . ? Cl1 O8 1.422(3) . ? Cl1 O7 1.438(2) . ? Cl2 O9 1.397(2) . ? Cl2 O10 1.409(3) . ? Cl2 O11 1.419(3) . ? Cl2 O12 1.426(3) . ? O1S H1SA 0.82(5) . ? O1S H1SB 0.65(6) . ? O2S H2SA 0.87(5) . ? O2S H2SB 0.80(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 O1 Cu1 N1 87.06(9) . . ? O1 Cu1 N3 171.95(8) . . ? N1 Cu1 N3 86.97(9) . . ? O1 Cu1 N4 92.33(8) . . ? N1 Cu1 N4 179.26(9) . . ? N3 Cu1 N4 93.68(9) . . ? O1 Cu1 N2 100.54(9) . . ? N1 Cu1 N2 94.19(10) . . ? N3 Cu1 N2 85.28(9) . . ? N4 Cu1 N2 85.51(9) . . ? O1 Cu1 O3 83.16(8) . . ? N1 Cu1 O3 87.13(9) . . ? N3 Cu1 O3 91.15(8) . . ? N4 Cu1 O3 93.22(8) . . ? N2 Cu1 O3 176.12(8) . . ? C11 O1 Cu1 122.94(19) . . ? C11 O2 H2 112(3) . . ? C1 O3 Cu1 122.1(2) . . ? C1 O4 H4 103(4) . . ? C4 N1 C16 110.8(2) . . ? C4 N1 C3 110.9(2) . . ? C16 N1 C3 104.1(2) . . ? C4 N1 Cu1 107.01(16) . . ? C16 N1 Cu1 110.56(18) . . ? C3 N1 Cu1 113.61(17) . . ? C13 N2 C18 113.0(3) . . ? C13 N2 C14 109.7(2) . . ? C18 N2 C14 111.9(2) . . ? C13 N2 Cu1 102.71(18) . . ? C18 N2 Cu1 106.60(18) . . ? C14 N2 Cu1 112.6(2) . . ? C17 N3 C5 111.2(2) . . ? C17 N3 C6 109.5(2) . . ? C5 N3 C6 108.0(2) . . ? C17 N3 Cu1 109.47(17) . . ? C5 N3 Cu1 105.05(16) . . ? C6 N3 Cu1 113.53(16) . . ? C9 N4 C8 107.7(2) . . ? C9 N4 C12 106.6(2) . . ? C8 N4 C12 110.4(2) . . ? C9 N4 Cu1 112.41(16) . . ? C8 N4 Cu1 112.54(16) . . ? C12 N4 Cu1 107.01(16) . . ? O3 C1 O4 122.7(3) . . ? O3 C1 C2 124.7(3) . . ? O4 C1 C2 112.6(3) . . ? C1 C2 C3 115.9(3) . . ? C1 C2 H2A 108.3 . . ? C3 C2 H2A 108.3 . . ? C1 C2 H2B 108.3 . . ? C3 C2 H2B 108.3 . . ? H2A C2 H2B 107.4 . . ? C2 C3 N1 118.7(2) . . ? C2 C3 H3A 107.6 . . ? N1 C3 H3A 107.6 . . ? C2 C3 H3B 107.6 . . ? N1 C3 H3B 107.6 . . ? H3A C3 H3B 107.1 . . ? N1 C4 C5 111.2(2) . . ? N1 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N1 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? N3 C5 C4 112.0(2) . . ? N3 C5 H5A 109.2 . . ? C4 C5 H5A 109.2 . . ? N3 C5 H5B 109.2 . . ? C4 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? N3 C6 C7 115.5(2) . . ? N3 C6 H6A 108.4 . . ? C7 C6 H6A 108.4 . . ? N3 C6 H6B 108.4 . . ? C7 C6 H6B 108.4 . . ? H6A C6 H6B 107.5 . . ? C6 C7 C8 116.2(2) . . ? C6 C7 H7A 108.2 . . ? C8 C7 H7A 108.2 . . ? C6 C7 H7B 108.2 . . ? C8 C7 H7B 108.2 . . ? H7A C7 H7B 107.4 . . ? N4 C8 C7 116.2(2) . . ? N4 C8 H8A 108.2 . . ? C7 C8 H8A 108.2 . . ? N4 C8 H8B 108.2 . . ? C7 C8 H8B 108.2 . . ? H8A C8 H8B 107.4 . . ? N4 C9 C10 115.8(2) . . ? N4 C9 H9A 108.3 . . ? C10 C9 H9A 108.3 . . ? N4 C9 H9B 108.3 . . ? C10 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C11 C10 C9 110.5(2) . . ? C11 C10 H10A 109.6 . . ? C9 C10 H10A 109.6 . . ? C11 C10 H10B 109.6 . . ? C9 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? O1 C11 O2 121.7(3) . . ? O1 C11 C10 122.2(3) . . ? O2 C11 C10 116.0(3) . . ? N4 C12 C13 111.8(2) . . ? N4 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N4 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? N2 C13 C12 111.7(2) . . ? N2 C13 H13A 109.3 . . ? C12 C13 H13A 109.3 . . ? N2 C13 H13B 109.3 . . ? C12 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? N2 C14 C15 114.3(3) . . ? N2 C14 H14A 108.7 . . ? C15 C14 H14A 108.7 . . ? N2 C14 H14B 108.7 . . ? C15 C14 H14B 108.7 . . ? H14A C14 H14B 107.6 . . ? C14 C15 C16 117.1(3) . . ? C14 C15 H15A 108.0 . . ? C16 C15 H15A 108.0 . . ? C14 C15 H15B 108.0 . . ? C16 C15 H15B 108.0 . . ? H15A C15 H15B 107.3 . . ? N1 C16 C15 118.3(3) . . ? N1 C16 H16A 107.7 . . ? C15 C16 H16A 107.7 . . ? N1 C16 H16B 107.7 . . ? C15 C16 H16B 107.7 . . ? H16A C16 H16B 107.1 . . ? N3 C17 C18 115.5(2) . . ? N3 C17 H17A 108.4 . . ? C18 C17 H17A 108.4 . . ? N3 C17 H17B 108.4 . . ? C18 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? N2 C18 C17 114.1(2) . . ? N2 C18 H18A 108.7 . . ? C17 C18 H18A 108.7 . . ? N2 C18 H18B 108.7 . . ? C17 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? O5 Cl1 O6 109.65(19) . . ? O5 Cl1 O8 110.16(19) . . ? O6 Cl1 O8 108.0(2) . . ? O5 Cl1 O7 110.27(15) . . ? O6 Cl1 O7 110.03(16) . . ? O8 Cl1 O7 108.65(16) . . ? O9 Cl2 O10 112.4(2) . . ? O9 Cl2 O11 108.04(16) . . ? O10 Cl2 O11 109.66(18) . . ? O9 Cl2 O12 109.5(2) . . ? O10 Cl2 O12 106.92(17) . . ? O11 Cl2 O12 110.4(2) . . ? H1SA O1S H1SB 105(6) . . ? H2SA O2S H2SB 112(5) . . ? 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 O2S H2SB O1S 0.80(4) 1.90(4) 2.690(7) 174(4) 2_646 O2S H2SA O11 0.87(5) 2.12(5) 2.958(4) 160(4) . O1S H1SB O12 0.65(6) 2.53(6) 3.119(5) 151(7) 2_556 O1S H1SB O10 0.65(6) 2.42(6) 3.011(5) 151(7) 2_556 O1S H1SA O7 0.82(5) 2.08(5) 2.902(5) 176(5) . O4 H4 O8 0.77(5) 1.99(5) 2.731(4) 159(5) . O2 H2 O2S 0.74(4) 1.83(4) 2.569(4) 173(4) 1_455 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.716 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.066 data_wong119a _database_code_depnum_ccdc_archive 'CCDC 635722' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H70 Cl3 Cu2 N8 Na3 O21' _chemical_formula_weight 1265.41 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' Na Na 0.0362 0.0249 '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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 15.6342(17) _cell_length_b 34.587(4) _cell_length_c 9.4238(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5095.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used 9904 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 27.43 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.649 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2632 _exptl_absorpt_coefficient_mu 1.103 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6667 _exptl_absorpt_correction_T_max 0.8096 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37107 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0486 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -44 _diffrn_reflns_limit_k_max 42 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.18 _diffrn_reflns_theta_max 27.43 _reflns_number_total 10941 _reflns_number_gt 9862 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0666P)^2^+5.6559P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.336(13) _refine_ls_number_reflns 10941 _refine_ls_number_parameters 670 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1355 _refine_ls_wR_factor_gt 0.1291 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.071 _refine_ls_shift/su_mean 0.009 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 0.73871(3) 1.077055(16) 0.50649(6) 0.02249(12) Uani 1 1 d . . . Cu2 Cu 0.74450(3) 0.816601(15) 0.56303(6) 0.02391(12) Uani 1 1 d . . . C1 C 0.7048(4) 0.83094(15) 0.2675(5) 0.0405(13) Uani 1 1 d . . . H1A H 0.7174 0.8460 0.1833 0.049 Uiso 1 1 calc R . . H1B H 0.6449 0.8237 0.2650 0.049 Uiso 1 1 calc R . . C1S C 0.8496(4) 1.05136(19) 1.0241(7) 0.0475(14) Uani 1 1 d . . . H1S1 H 0.8622 1.0687 0.9473 0.071 Uiso 1 1 calc R . . H1S2 H 0.8383 1.0660 1.1085 0.071 Uiso 1 1 calc R . . H1S3 H 0.8003 1.0361 1.0007 0.071 Uiso 1 1 calc R . . C2 C 0.7608(5) 0.79488(19) 0.2716(6) 0.0494(16) Uani 1 1 d . . . H2A H 0.7461 0.7780 0.1932 0.059 Uiso 1 1 calc R . . H2B H 0.8205 0.8021 0.2620 0.059 Uiso 1 1 calc R . . C3 C 0.8204(4) 0.74684(18) 0.4250(7) 0.0460(15) Uani 1 1 d . . . H3A H 0.8733 0.7610 0.4101 0.055 Uiso 1 1 calc R . . H3B H 0.8163 0.7273 0.3513 0.055 Uiso 1 1 calc R . . C4 C 0.8249(4) 0.72666(15) 0.5685(8) 0.0493(14) Uani 1 1 d . . . H4A H 0.7729 0.7118 0.5809 0.059 Uiso 1 1 calc R . . H4B H 0.8722 0.7085 0.5662 0.059 Uiso 1 1 calc R . . C5 C 0.8357(4) 0.75190(19) 0.6945(8) 0.0501(15) Uani 1 1 d . . . H5A H 0.8873 0.7670 0.6813 0.060 Uiso 1 1 calc R . . H5B H 0.8448 0.7355 0.7765 0.060 Uiso 1 1 calc R . . C6 C 0.7840(5) 0.79991(17) 0.8638(6) 0.0484(16) Uani 1 1 d . . . H6A H 0.7995 0.7807 0.9341 0.058 Uiso 1 1 calc R . . H6B H 0.7328 0.8128 0.8973 0.058 Uiso 1 1 calc R . . C7 C 0.8556(4) 0.82961(17) 0.8561(6) 0.0454(14) Uani 1 1 d . . . H7A H 0.9057 0.8177 0.8138 0.054 Uiso 1 1 calc R . . H7B H 0.8707 0.8376 0.9516 0.054 Uiso 1 1 calc R . . C8 C 0.8307(4) 0.86495(14) 0.7698(5) 0.0312(11) Uani 1 1 d . . . C9 C 0.6523(4) 0.88097(17) 0.4282(7) 0.0468(14) Uani 1 1 d . . . H9A H 0.6471 0.8991 0.3502 0.056 Uiso 1 1 calc R . . H9B H 0.6679 0.8956 0.5120 0.056 Uiso 1 1 calc R . . C10 C 0.5663(4) 0.86300(19) 0.4533(9) 0.0564(18) Uani 1 1 d . . . H10A H 0.5523 0.8472 0.3716 0.068 Uiso 1 1 calc R . . H10B H 0.5242 0.8836 0.4581 0.068 Uiso 1 1 calc R . . C11 C 0.5569(4) 0.83760(17) 0.5890(9) 0.0545(17) Uani 1 1 d . . . H11B H 0.5726 0.8528 0.6714 0.065 Uiso 1 1 calc R . . H11C H 0.4974 0.8301 0.5996 0.065 Uiso 1 1 calc R . . C12 C 0.6065(4) 0.78352(19) 0.7255(6) 0.0465(14) Uani 1 1 d . . . H12A H 0.5546 0.7682 0.7317 0.056 Uiso 1 1 calc R . . H12B H 0.6043 0.8031 0.7991 0.056 Uiso 1 1 calc R . . C13 C 0.6823(4) 0.75789(16) 0.7505(5) 0.0372(12) Uani 1 1 d . . . H13A H 0.6804 0.7479 0.8466 0.045 Uiso 1 1 calc R . . H13B H 0.6802 0.7361 0.6857 0.045 Uiso 1 1 calc R . . C14 C 0.6625(4) 0.75355(15) 0.4130(6) 0.0360(12) Uani 1 1 d . . . H14A H 0.6484 0.7456 0.3171 0.043 Uiso 1 1 calc R . . H14B H 0.6690 0.7302 0.4692 0.043 Uiso 1 1 calc R . . C15 C 0.5889(3) 0.77591(17) 0.4710(6) 0.0410(13) Uani 1 1 d . . . H15A H 0.5629 0.7904 0.3941 0.049 Uiso 1 1 calc R . . H15B H 0.5464 0.7578 0.5059 0.049 Uiso 1 1 calc R . . C16 C 0.8075(3) 0.87509(15) 0.3825(5) 0.0317(11) Uani 1 1 d . . . H16A H 0.8530 0.8560 0.3810 0.038 Uiso 1 1 calc R . . H16B H 0.8153 0.8907 0.4671 0.038 Uiso 1 1 calc R . . C17 C 0.8184(4) 0.90134(16) 0.2532(5) 0.0393(13) Uani 1 1 d . . . H17A H 0.8366 0.8859 0.1727 0.047 Uiso 1 1 calc R . . H17B H 0.7637 0.9129 0.2297 0.047 Uiso 1 1 calc R . . C18 C 0.8832(3) 0.93295(13) 0.2797(5) 0.0235(9) Uani 1 1 d . . . C19 C 0.7325(3) 1.16182(15) 0.5075(7) 0.0408(12) Uani 1 1 d . . . H19A H 0.7644 1.1858 0.5014 0.049 Uiso 1 1 calc R . . H19B H 0.6846 1.1659 0.5712 0.049 Uiso 1 1 calc R . . C20 C 0.6990(4) 1.15120(17) 0.3612(7) 0.0456(14) Uani 1 1 d . . . H20A H 0.6609 1.1714 0.3277 0.055 Uiso 1 1 calc R . . H20B H 0.7465 1.1493 0.2953 0.055 Uiso 1 1 calc R . . C21 C 0.6454(4) 1.09949(19) 0.2185(6) 0.0472(16) Uani 1 1 d . . . H21A H 0.7015 1.1002 0.1746 0.057 Uiso 1 1 calc R . . H21B H 0.6082 1.1166 0.1651 0.057 Uiso 1 1 calc R . . C22 C 0.6104(4) 1.05847(19) 0.2097(6) 0.0447(14) Uani 1 1 d . . . H22A H 0.5545 1.0581 0.2545 0.054 Uiso 1 1 calc R . . H22B H 0.6022 1.0521 0.1104 0.054 Uiso 1 1 calc R . . C23 C 0.6635(3) 1.02722(18) 0.2755(5) 0.0386(13) Uani 1 1 d . . . H23A H 0.7193 1.0279 0.2304 0.046 Uiso 1 1 calc R . . H23B H 0.6375 1.0027 0.2504 0.046 Uiso 1 1 calc R . . C24 C 0.7321(3) 0.99155(15) 0.4529(5) 0.0283(10) Uani 1 1 d . . . H24A H 0.7853 0.9956 0.4021 0.034 Uiso 1 1 calc R . . H24B H 0.7030 0.9701 0.4075 0.034 Uiso 1 1 calc R . . C25 C 0.7541(3) 0.97940(13) 0.6025(5) 0.0284(10) Uani 1 1 d . . . H25A H 0.7752 0.9530 0.6004 0.034 Uiso 1 1 calc R . . H25B H 0.7022 0.9796 0.6590 0.034 Uiso 1 1 calc R . . C26 C 0.8202(3) 1.00467(13) 0.6751(5) 0.0222(9) Uani 1 1 d . . . C27 C 0.7958(4) 1.13463(16) 0.7231(6) 0.0375(12) Uani 1 1 d . . . H27A H 0.8206 1.1597 0.7439 0.045 Uiso 1 1 calc R . . H27B H 0.8353 1.1152 0.7579 0.045 Uiso 1 1 calc R . . C28 C 0.7122(4) 1.13094(16) 0.8062(6) 0.0402(12) Uani 1 1 d . . . H28A H 0.7245 1.1355 0.9057 0.048 Uiso 1 1 calc R . . H28B H 0.6739 1.1513 0.7751 0.048 Uiso 1 1 calc R . . C29 C 0.6651(3) 1.09265(16) 0.7937(5) 0.0342(12) Uani 1 1 d . . . H29A H 0.7022 1.0723 0.8285 0.041 Uiso 1 1 calc R . . H29B H 0.6152 1.0935 0.8547 0.041 Uiso 1 1 calc R . . C30 C 0.6011(3) 1.04262(14) 0.6542(5) 0.0309(10) Uani 1 1 d . . . H30A H 0.5444 1.0436 0.6960 0.037 Uiso 1 1 calc R . . H30B H 0.6370 1.0270 0.7153 0.037 Uiso 1 1 calc R . . C31 C 0.5955(3) 1.02382(15) 0.5097(6) 0.0311(10) Uani 1 1 d . . . H31A H 0.5805 0.9968 0.5207 0.037 Uiso 1 1 calc R . . H31B H 0.5508 1.0362 0.4547 0.037 Uiso 1 1 calc R . . C32 C 0.5695(3) 1.11692(18) 0.4360(6) 0.0391(13) Uani 1 1 d . . . H32A H 0.5312 1.0979 0.3950 0.047 Uiso 1 1 calc R . . H32B H 0.5456 1.1422 0.4161 0.047 Uiso 1 1 calc R . . C33 C 0.5710(3) 1.11112(16) 0.5971(6) 0.0327(11) Uani 1 1 d . . . H33A H 0.5822 1.1358 0.6422 0.039 Uiso 1 1 calc R . . H33B H 0.5150 1.1025 0.6278 0.039 Uiso 1 1 calc R . . C34 C 0.8762(3) 1.13659(15) 0.5037(7) 0.0389(12) Uani 1 1 d . . . H34A H 0.9029 1.1586 0.5499 0.047 Uiso 1 1 calc R . . H34B H 0.8694 1.1430 0.4042 0.047 Uiso 1 1 calc R . . C35 C 0.9356(3) 1.10223(14) 0.5155(6) 0.0345(11) Uani 1 1 d . . . H35A H 0.9335 1.0924 0.6118 0.041 Uiso 1 1 calc R . . H35B H 0.9937 1.1107 0.4970 0.041 Uiso 1 1 calc R . . C36 C 0.9130(3) 1.06978(13) 0.4133(5) 0.0250(9) Uani 1 1 d . . . O1 O 0.88284(19) 0.98726(9) 0.7311(3) 0.0255(7) Uani 1 1 d . . . O1S O 0.9225(2) 1.02595(10) 1.0482(4) 0.0359(8) Uani 1 1 d . . . O2 O 0.8108(2) 1.04031(9) 0.6744(4) 0.0284(7) Uani 1 1 d . . . O3 O 0.9724(2) 1.04937(9) 0.3674(4) 0.0275(7) Uani 1 1 d . . . O4 O 0.8359(2) 1.06550(10) 0.3788(4) 0.0285(7) Uani 1 1 d . . . O5 O 0.8669(3) 0.89605(11) 0.7937(4) 0.0404(9) Uani 1 1 d . . . O6 O 0.7723(3) 0.86118(11) 0.6747(4) 0.0406(9) Uani 1 1 d . . . O7 O 0.9023(2) 0.95397(10) 0.1759(3) 0.0308(8) Uani 1 1 d . . . O8 O 0.9113(2) 0.93777(10) 0.4019(3) 0.0295(7) Uani 1 1 d . . . O9 O 0.7274(3) 0.9625(2) 0.9619(7) 0.0861(19) Uani 1 1 d . . . O10 O 0.6821(5) 0.9004(2) 0.9609(8) 0.124(3) Uani 1 1 d . . . O11 O 0.6004(3) 0.9455(2) 0.8487(7) 0.096(2) Uani 1 1 d . . . O12 O 0.6102(3) 0.94352(17) 1.0959(6) 0.0759(16) Uani 1 1 d . . . O13 O 1.0350(4) 0.87363(13) 0.6537(7) 0.0768(17) Uani 1 1 d . . . O14 O 1.0240(8) 0.8101(2) 0.6276(19) 0.261(10) Uani 1 1 d . . . O15 O 1.1474(3) 0.83820(16) 0.5660(8) 0.0851(17) Uani 1 1 d . . . O16 O 1.0330(8) 0.8423(5) 0.4410(12) 0.231(8) Uani 1 1 d . . . O17 O 0.9712(7) 0.7670(2) 0.1484(11) 0.163(5) Uani 1 1 d . . . O18 O 0.9586(4) 0.70350(17) 0.1987(6) 0.0826(17) Uani 1 1 d . . . O19 O 1.0740(4) 0.7254(3) 0.0711(7) 0.140(4) Uani 1 1 d . . . O20 O 0.9466(4) 0.7224(3) -0.0370(6) 0.111(3) Uani 1 1 d . . . Cl1 Cl 0.65294(9) 0.94058(6) 0.96477(16) 0.0562(4) Uani 1 1 d . . . Cl2 Cl 1.05779(10) 0.84123(4) 0.57489(19) 0.0503(4) Uani 1 1 d . . . Cl3 Cl 0.98792(9) 0.73016(5) 0.09219(15) 0.0485(3) Uani 1 1 d . . . N1 N 0.6524(3) 1.11394(12) 0.3649(4) 0.0333(9) Uani 1 1 d . . . N2 N 0.7897(2) 1.13058(11) 0.5672(5) 0.0308(8) Uani 1 1 d . . . N3 N 0.6368(2) 1.08245(12) 0.6463(4) 0.0278(8) Uani 1 1 d . . . N4 N 0.6778(2) 1.02698(11) 0.4330(4) 0.0236(8) Uani 1 1 d . . . N5 N 0.6102(3) 0.80264(12) 0.5847(5) 0.0363(10) Uani 1 1 d . . . N6 N 0.7631(3) 0.77954(13) 0.7288(5) 0.0336(10) Uani 1 1 d . . . N7 N 0.7476(3) 0.77408(13) 0.4093(5) 0.0323(10) Uani 1 1 d . . . N8 N 0.7226(3) 0.85386(12) 0.3954(4) 0.0317(9) Uani 1 1 d . . . Na1 Na 0.87365(12) 0.94769(5) 0.93644(18) 0.0266(4) Uani 1 1 d . . . Na2 Na 0.99627(12) 1.01477(5) 0.8338(2) 0.0313(4) Uani 1 1 d . . . Na3 Na 0.95514(11) 0.93160(5) 0.63690(17) 0.0232(4) 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 0.0167(2) 0.0224(3) 0.0284(2) 0.0018(2) 0.0022(2) 0.00396(19) Cu2 0.0284(3) 0.0204(3) 0.0229(2) 0.0018(2) -0.0007(2) -0.0056(2) C1 0.063(4) 0.030(3) 0.028(2) 0.009(2) -0.013(2) -0.021(3) C1S 0.037(3) 0.058(4) 0.048(3) -0.003(3) 0.003(3) 0.007(3) C2 0.076(5) 0.045(4) 0.027(3) -0.003(2) 0.007(3) -0.019(3) C3 0.052(4) 0.032(3) 0.054(3) -0.004(3) 0.021(3) 0.008(3) C4 0.042(3) 0.025(3) 0.081(4) 0.000(3) -0.010(3) 0.010(2) C5 0.041(3) 0.045(4) 0.065(4) 0.013(3) -0.008(3) 0.000(3) C6 0.082(5) 0.038(3) 0.025(2) 0.011(2) -0.007(3) -0.023(3) C7 0.065(4) 0.036(3) 0.035(3) 0.002(2) -0.018(3) -0.022(3) C8 0.046(3) 0.024(3) 0.023(2) -0.0012(18) 0.008(2) -0.010(2) C9 0.047(3) 0.033(3) 0.060(4) 0.008(3) -0.013(3) 0.004(2) C10 0.041(3) 0.037(3) 0.092(5) 0.011(3) -0.015(3) -0.002(3) C11 0.033(3) 0.037(3) 0.094(5) 0.006(3) 0.008(3) 0.004(2) C12 0.042(3) 0.053(4) 0.044(3) 0.003(3) 0.015(3) -0.011(3) C13 0.049(3) 0.035(3) 0.028(2) 0.010(2) -0.001(2) -0.017(2) C14 0.049(3) 0.025(3) 0.034(2) 0.007(2) -0.011(2) -0.015(2) C15 0.030(3) 0.044(3) 0.049(3) 0.013(2) -0.009(2) -0.015(2) C16 0.041(3) 0.028(3) 0.026(2) 0.003(2) -0.008(2) -0.017(2) C17 0.061(4) 0.035(3) 0.022(2) 0.004(2) -0.009(2) -0.028(3) C18 0.026(2) 0.018(2) 0.026(2) 0.0038(17) 0.0000(17) -0.0069(17) C19 0.042(3) 0.024(3) 0.056(3) 0.008(3) 0.011(3) 0.010(2) C20 0.046(3) 0.038(3) 0.052(3) 0.018(3) 0.010(3) 0.010(3) C21 0.044(3) 0.067(4) 0.030(3) 0.016(3) 0.002(2) 0.023(3) C22 0.038(3) 0.066(4) 0.030(3) 0.001(3) -0.007(2) 0.010(3) C23 0.033(3) 0.059(4) 0.024(2) -0.006(2) -0.003(2) 0.000(2) C24 0.026(2) 0.028(3) 0.031(2) -0.0066(19) -0.0051(19) 0.0025(19) C25 0.030(2) 0.018(2) 0.037(3) 0.0029(18) -0.0097(19) -0.0010(18) C26 0.019(2) 0.025(2) 0.0225(19) 0.0031(17) 0.0000(16) -0.0003(17) C27 0.039(3) 0.029(3) 0.045(3) -0.004(2) 0.002(2) -0.001(2) C28 0.047(3) 0.038(3) 0.036(3) -0.009(2) 0.002(2) 0.008(2) C29 0.035(3) 0.036(3) 0.032(2) 0.003(2) 0.005(2) 0.011(2) C30 0.022(2) 0.033(3) 0.038(3) 0.008(2) 0.002(2) 0.0001(19) C31 0.020(2) 0.037(3) 0.036(2) 0.003(2) -0.007(2) -0.0025(18) C32 0.030(3) 0.046(3) 0.041(3) 0.014(2) -0.001(2) 0.019(2) C33 0.022(2) 0.039(3) 0.037(3) 0.005(2) 0.002(2) 0.007(2) C34 0.032(3) 0.028(3) 0.057(3) -0.007(3) 0.010(3) -0.0031(19) C35 0.026(2) 0.028(3) 0.049(3) -0.007(2) 0.005(2) -0.0013(18) C36 0.022(2) 0.026(2) 0.026(2) 0.0093(18) 0.0073(17) 0.0001(18) O1 0.0224(16) 0.0234(16) 0.0307(16) 0.0030(13) -0.0046(13) 0.0019(12) O1S 0.0354(19) 0.042(2) 0.0303(18) 0.0062(15) 0.0063(14) -0.0017(15) O2 0.0268(17) 0.0219(17) 0.0365(17) 0.0001(14) -0.0135(14) 0.0041(13) O3 0.0221(16) 0.0265(17) 0.0339(17) 0.0007(14) 0.0078(13) 0.0022(13) O4 0.0197(17) 0.0322(18) 0.0335(17) -0.0002(14) 0.0054(13) 0.0012(13) O5 0.049(2) 0.034(2) 0.0388(19) -0.0099(16) 0.0105(17) -0.0158(17) O6 0.064(3) 0.0266(19) 0.0316(18) -0.0014(15) -0.0093(18) -0.0071(17) O7 0.0362(19) 0.0330(19) 0.0230(15) 0.0010(14) 0.0014(14) -0.0137(15) O8 0.0386(19) 0.0294(18) 0.0206(15) 0.0048(13) -0.0053(13) -0.0150(15) O9 0.038(3) 0.136(6) 0.084(4) -0.004(4) 0.004(3) -0.032(3) O10 0.152(7) 0.123(6) 0.096(5) -0.016(5) 0.011(5) 0.052(6) O11 0.040(3) 0.172(7) 0.075(4) 0.036(4) -0.013(3) -0.025(3) O12 0.053(3) 0.101(4) 0.074(3) -0.016(3) 0.029(3) -0.021(3) O13 0.083(4) 0.036(3) 0.112(5) -0.017(3) 0.017(3) 0.023(2) O14 0.268(13) 0.053(4) 0.46(2) -0.048(8) 0.283(15) -0.039(6) O15 0.069(3) 0.069(3) 0.118(5) -0.010(4) 0.029(4) 0.019(3) O16 0.180(11) 0.39(2) 0.123(8) -0.084(11) -0.062(8) 0.099(12) O17 0.239(11) 0.059(4) 0.192(10) -0.018(5) 0.117(9) -0.007(5) O18 0.104(5) 0.081(4) 0.063(3) 0.010(3) -0.005(3) -0.026(3) O19 0.058(4) 0.308(12) 0.054(3) 0.025(6) -0.006(3) 0.017(5) O20 0.086(4) 0.187(8) 0.060(4) 0.009(4) -0.028(3) -0.009(5) Cl1 0.0231(7) 0.0999(14) 0.0456(7) 0.0038(8) 0.0037(6) -0.0050(7) Cl2 0.0491(8) 0.0385(7) 0.0635(9) -0.0152(7) 0.0064(7) 0.0091(6) Cl3 0.0435(8) 0.0642(10) 0.0376(7) -0.0003(6) -0.0070(6) 0.0012(7) N1 0.034(2) 0.032(2) 0.033(2) 0.0070(18) 0.0003(18) 0.0141(18) N2 0.0258(19) 0.0211(19) 0.045(2) 0.0018(19) 0.0111(19) 0.0048(15) N3 0.023(2) 0.026(2) 0.034(2) 0.0054(17) 0.0025(16) 0.0067(15) N4 0.0206(18) 0.027(2) 0.0237(18) -0.0029(15) -0.0046(15) 0.0024(15) N5 0.028(2) 0.030(2) 0.051(3) 0.003(2) 0.005(2) 0.0018(17) N6 0.037(2) 0.031(2) 0.034(2) 0.0084(18) -0.0084(18) -0.0127(18) N7 0.043(3) 0.026(2) 0.028(2) 0.0007(17) 0.0056(17) -0.0039(17) N8 0.045(3) 0.022(2) 0.028(2) 0.0050(17) -0.0101(18) -0.0107(18) Na1 0.0314(10) 0.0276(10) 0.0210(8) 0.0025(7) 0.0013(7) -0.0005(7) Na2 0.0307(10) 0.0267(10) 0.0363(10) -0.0055(8) 0.0032(8) -0.0123(8) Na3 0.0275(9) 0.0206(9) 0.0215(8) -0.0009(7) -0.0016(7) -0.0006(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.979(3) . ? Cu1 N3 2.076(4) . ? Cu1 N4 2.094(4) . ? Cu1 N2 2.095(4) . ? Cu1 N1 2.287(4) . ? Cu1 O2 2.322(3) . ? Cu2 O6 1.917(4) . ? Cu2 N6 2.042(4) . ? Cu2 N7 2.065(5) . ? Cu2 N8 2.068(4) . ? Cu2 N5 2.165(4) . ? C1 N8 1.469(6) . ? C1 C2 1.525(10) . ? C1S O1S 1.457(6) . ? C2 N7 1.498(7) . ? C3 N7 1.485(7) . ? C3 C4 1.524(9) . ? C4 C5 1.483(10) . ? C5 N6 1.519(8) . ? C6 N6 1.491(7) . ? C6 C7 1.521(8) . ? C7 C8 1.519(8) . ? C8 O5 1.236(6) . ? C8 O6 1.287(6) . ? C9 N8 1.478(8) . ? C9 C10 1.499(9) . ? C10 C11 1.559(10) . ? C11 N5 1.469(7) . ? C12 N5 1.483(7) . ? C12 C13 1.499(9) . ? C13 N6 1.483(6) . ? C14 C15 1.491(8) . ? C14 N7 1.508(7) . ? C15 N5 1.454(7) . ? C16 N8 1.522(6) . ? C16 C17 1.529(6) . ? C17 C18 1.512(6) . ? C18 O8 1.243(5) . ? C18 O7 1.255(5) . ? C18 Na2 2.661(5) 2_774 ? C19 N2 1.511(6) . ? C19 C20 1.521(9) . ? C20 N1 1.481(7) . ? C21 N1 1.471(7) . ? C21 C22 1.523(9) . ? C22 C23 1.497(8) . ? C23 N4 1.501(6) . ? C24 N4 1.502(6) . ? C24 C25 1.511(7) . ? C25 C26 1.516(6) . ? C26 O2 1.241(5) . ? C26 O1 1.265(5) . ? C27 N2 1.478(7) . ? C27 C28 1.530(8) . ? C28 C29 1.519(8) . ? C29 N3 1.500(7) . ? C30 N3 1.488(6) . ? C30 C31 1.512(7) . ? C31 N4 1.481(6) . ? C32 N1 1.463(7) . ? C32 C33 1.531(7) . ? C33 N3 1.502(6) . ? C34 N2 1.495(6) . ? C34 C35 1.512(7) . ? C35 C36 1.520(7) . ? C36 O3 1.244(5) . ? C36 O4 1.257(6) . ? O1 Na2 2.233(4) . ? O1 Na1 2.375(4) . ? O1 Na3 2.402(4) . ? O1S Na2 2.359(4) . ? O1S Na3 2.552(4) 2_775 ? O1S Na1 3.003(4) . ? O3 Na2 2.294(4) 2_774 ? O3 Na1 2.496(4) 2_774 ? O3 Na3 2.537(4) 2_774 ? O5 Na1 2.238(4) . ? O5 Na3 2.366(4) . ? O7 Na1 2.311(4) 1_554 ? O7 Na2 2.429(4) 2_774 ? O8 Na2 2.280(4) 2_774 ? O8 Na3 2.328(3) . ? O9 Cl1 1.391(5) . ? O9 Na1 2.355(6) . ? O10 Cl1 1.463(8) . ? O11 Cl1 1.379(6) . ? O12 Cl1 1.409(5) . ? O13 Cl2 1.391(5) . ? O13 Na3 2.367(5) . ? O14 Cl2 1.298(8) . ? O15 Cl2 1.408(5) . ? O16 Cl2 1.321(10) . ? O17 Cl3 1.405(7) . ? O18 Cl3 1.438(6) . ? O19 Cl3 1.370(6) . ? O20 Cl3 1.404(6) . ? Na1 O7 2.311(4) 1_556 ? Na1 O3 2.496(4) 2_775 ? Na1 Na3 3.147(2) . ? Na1 Na2 3.161(3) . ? Na2 O8 2.280(4) 2_775 ? Na2 O3 2.294(4) 2_775 ? Na2 O7 2.429(4) 2_775 ? Na2 C18 2.661(5) 2_775 ? Na2 Na3 3.483(2) . ? Na2 Na3 3.490(3) 2_775 ? Na3 O3 2.537(4) 2_775 ? Na3 O1S 2.552(4) 2_774 ? Na3 Na2 3.490(3) 2_774 ? 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 O4 Cu1 N3 173.39(15) . . ? O4 Cu1 N4 88.91(15) . . ? N3 Cu1 N4 86.29(16) . . ? O4 Cu1 N2 93.02(15) . . ? N3 Cu1 N2 92.24(16) . . ? N4 Cu1 N2 173.72(16) . . ? O4 Cu1 N1 102.19(15) . . ? N3 Cu1 N1 82.37(15) . . ? N4 Cu1 N1 90.02(16) . . ? N2 Cu1 N1 83.73(17) . . ? O4 Cu1 O2 86.04(13) . . ? N3 Cu1 O2 89.39(14) . . ? N4 Cu1 O2 89.61(13) . . ? N2 Cu1 O2 96.49(15) . . ? N1 Cu1 O2 171.75(14) . . ? O6 Cu2 N6 93.02(17) . . ? O6 Cu2 N7 162.35(18) . . ? N6 Cu2 N7 94.95(17) . . ? O6 Cu2 N8 87.47(16) . . ? N6 Cu2 N8 178.63(18) . . ? N7 Cu2 N8 84.94(17) . . ? O6 Cu2 N5 110.32(18) . . ? N6 Cu2 N5 85.75(17) . . ? N7 Cu2 N5 85.99(17) . . ? N8 Cu2 N5 92.88(18) . . ? N8 C1 C2 108.2(4) . . ? N7 C2 C1 109.6(5) . . ? N7 C3 C4 114.5(5) . . ? C5 C4 C3 116.5(5) . . ? C4 C5 N6 117.1(5) . . ? N6 C6 C7 116.1(5) . . ? C6 C7 C8 112.3(5) . . ? O5 C8 O6 122.7(5) . . ? O5 C8 C7 119.0(5) . . ? O6 C8 C7 118.3(4) . . ? N8 C9 C10 115.9(5) . . ? C9 C10 C11 116.6(5) . . ? N5 C11 C10 112.8(6) . . ? N5 C12 C13 111.9(4) . . ? N6 C13 C12 110.7(4) . . ? C15 C14 N7 116.4(4) . . ? N5 C15 C14 115.0(4) . . ? N8 C16 C17 116.5(4) . . ? C18 C17 C16 111.9(4) . . ? O8 C18 O7 124.1(4) . . ? O8 C18 C17 119.1(4) . . ? O7 C18 C17 116.7(4) . . ? O8 C18 Na2 58.8(2) . 2_774 ? O7 C18 Na2 65.6(2) . 2_774 ? C17 C18 Na2 176.4(4) . 2_774 ? N2 C19 C20 111.7(4) . . ? N1 C20 C19 111.0(4) . . ? N1 C21 C22 113.2(5) . . ? C23 C22 C21 116.8(5) . . ? C22 C23 N4 119.8(5) . . ? N4 C24 C25 118.1(4) . . ? C24 C25 C26 114.6(4) . . ? O2 C26 O1 124.5(4) . . ? O2 C26 C25 119.3(4) . . ? O1 C26 C25 116.2(4) . . ? N2 C27 C28 116.4(5) . . ? C29 C28 C27 116.5(4) . . ? N3 C29 C28 114.8(4) . . ? N3 C30 C31 112.0(4) . . ? N4 C31 C30 110.9(4) . . ? N1 C32 C33 115.5(4) . . ? N3 C33 C32 113.8(4) . . ? N2 C34 C35 114.7(4) . . ? C34 C35 C36 113.0(4) . . ? O3 C36 O4 123.9(5) . . ? O3 C36 C35 117.8(4) . . ? O4 C36 C35 118.3(4) . . ? C26 O1 Na2 126.4(3) . . ? C26 O1 Na1 124.6(3) . . ? Na2 O1 Na1 86.57(12) . . ? C26 O1 Na3 126.3(3) . . ? Na2 O1 Na3 97.34(13) . . ? Na1 O1 Na3 82.40(11) . . ? C1S O1S Na2 110.3(3) . . ? C1S O1S Na3 106.9(3) . 2_775 ? Na2 O1S Na3 90.48(13) . 2_775 ? C1S O1S Na1 106.9(3) . . ? Na2 O1S Na1 71.10(11) . . ? Na3 O1S Na1 145.49(15) 2_775 . ? C26 O2 Cu1 127.2(3) . . ? C36 O3 Na2 139.2(3) . 2_774 ? C36 O3 Na1 127.3(3) . 2_774 ? Na2 O3 Na1 82.48(12) 2_774 2_774 ? C36 O3 Na3 118.9(3) . 2_774 ? Na2 O3 Na3 92.13(12) 2_774 2_774 ? Na1 O3 Na3 77.39(10) 2_774 2_774 ? C36 O4 Cu1 123.7(3) . . ? C8 O5 Na1 145.6(3) . . ? C8 O5 Na3 127.3(3) . . ? Na1 O5 Na3 86.17(13) . . ? C8 O6 Cu2 128.7(4) . . ? C18 O7 Na1 131.4(3) . 1_554 ? C18 O7 Na2 86.3(3) . 2_774 ? Na1 O7 Na2 140.05(16) 1_554 2_774 ? C18 O8 Na2 93.4(3) . 2_774 ? C18 O8 Na3 166.5(3) . . ? Na2 O8 Na3 98.45(13) 2_774 . ? Cl1 O9 Na1 134.1(5) . . ? Cl2 O13 Na3 141.4(4) . . ? O11 Cl1 O9 114.6(4) . . ? O11 Cl1 O12 113.8(4) . . ? O9 Cl1 O12 112.0(4) . . ? O11 Cl1 O10 106.4(5) . . ? O9 Cl1 O10 104.9(5) . . ? O12 Cl1 O10 103.8(4) . . ? O14 Cl2 O16 105.6(11) . . ? O14 Cl2 O13 111.1(5) . . ? O16 Cl2 O13 114.4(7) . . ? O14 Cl2 O15 111.5(7) . . ? O16 Cl2 O15 103.7(7) . . ? O13 Cl2 O15 110.3(4) . . ? O19 Cl3 O20 107.6(4) . . ? O19 Cl3 O17 110.3(6) . . ? O20 Cl3 O17 114.5(7) . . ? O19 Cl3 O18 109.7(5) . . ? O20 Cl3 O18 109.7(4) . . ? O17 Cl3 O18 105.0(5) . . ? C32 N1 C21 112.8(5) . . ? C32 N1 C20 112.7(4) . . ? C21 N1 C20 108.1(5) . . ? C32 N1 Cu1 107.2(3) . . ? C21 N1 Cu1 113.7(3) . . ? C20 N1 Cu1 102.1(3) . . ? C27 N2 C34 109.0(4) . . ? C27 N2 C19 109.9(4) . . ? C34 N2 C19 106.7(4) . . ? C27 N2 Cu1 112.3(3) . . ? C34 N2 Cu1 111.0(3) . . ? C19 N2 Cu1 107.8(3) . . ? C30 N3 C29 106.4(4) . . ? C30 N3 C33 111.7(4) . . ? C29 N3 C33 109.5(4) . . ? C30 N3 Cu1 103.7(3) . . ? C29 N3 Cu1 112.5(3) . . ? C33 N3 Cu1 112.9(3) . . ? C31 N4 C24 111.7(4) . . ? C31 N4 C23 110.7(4) . . ? C24 N4 C23 102.3(4) . . ? C31 N4 Cu1 107.1(3) . . ? C24 N4 Cu1 112.1(3) . . ? C23 N4 Cu1 113.0(3) . . ? C15 N5 C11 114.4(5) . . ? C15 N5 C12 111.5(4) . . ? C11 N5 C12 108.7(5) . . ? C15 N5 Cu2 107.1(3) . . ? C11 N5 Cu2 111.7(3) . . ? C12 N5 Cu2 102.8(3) . . ? C13 N6 C6 108.0(4) . . ? C13 N6 C5 110.4(4) . . ? C6 N6 C5 108.4(5) . . ? C13 N6 Cu2 107.5(3) . . ? C6 N6 Cu2 112.8(3) . . ? C5 N6 Cu2 109.8(4) . . ? C3 N7 C2 106.6(5) . . ? C3 N7 C14 112.0(5) . . ? C2 N7 C14 111.6(4) . . ? C3 N7 Cu2 113.6(4) . . ? C2 N7 Cu2 105.6(3) . . ? C14 N7 Cu2 107.4(3) . . ? C1 N8 C9 111.9(5) . . ? C1 N8 C16 111.1(4) . . ? C9 N8 C16 111.1(4) . . ? C1 N8 Cu2 108.8(3) . . ? C9 N8 Cu2 111.0(3) . . ? C16 N8 Cu2 102.5(3) . . ? O5 Na1 O7 132.14(16) . 1_556 ? O5 Na1 O9 100.9(2) . . ? O7 Na1 O9 93.90(19) 1_556 . ? O5 Na1 O1 88.44(14) . . ? O7 Na1 O1 136.89(14) 1_556 . ? O9 Na1 O1 90.93(19) . . ? O5 Na1 O3 85.48(14) . 2_775 ? O7 Na1 O3 93.66(13) 1_556 2_775 ? O9 Na1 O3 162.5(2) . 2_775 ? O1 Na1 O3 72.89(11) . 2_775 ? O5 Na1 O1S 160.37(14) . . ? O7 Na1 O1S 61.54(11) 1_556 . ? O9 Na1 O1S 90.84(19) . . ? O1 Na1 O1S 75.60(11) . . ? O3 Na1 O1S 79.02(11) 2_775 . ? O5 Na1 Na3 48.61(10) . . ? O7 Na1 Na3 144.51(12) 1_556 . ? O9 Na1 Na3 121.54(17) . . ? O1 Na1 Na3 49.18(9) . . ? O3 Na1 Na3 51.89(9) 2_775 . ? O1S Na1 Na3 111.78(9) . . ? O5 Na1 Na2 115.48(12) . . ? O7 Na1 Na2 96.45(10) 1_556 . ? O9 Na1 Na2 117.38(19) . . ? O1 Na1 Na2 44.85(9) . . ? O3 Na1 Na2 46.01(9) 2_775 . ? O1S Na1 Na2 44.90(8) . . ? Na3 Na1 Na2 67.03(6) . . ? O1 Na2 O8 158.82(16) . 2_775 ? O1 Na2 O3 79.49(12) . 2_775 ? O8 Na2 O3 121.46(15) 2_775 2_775 ? O1 Na2 O1S 93.04(14) . . ? O8 Na2 O1S 87.18(13) 2_775 . ? O3 Na2 O1S 98.32(14) 2_775 . ? O1 Na2 O7 116.28(14) . 2_775 ? O8 Na2 O7 55.79(11) 2_775 2_775 ? O3 Na2 O7 112.06(14) 2_775 2_775 ? O1S Na2 O7 140.46(14) . 2_775 ? O1 Na2 C18 140.25(15) . 2_775 ? O8 Na2 C18 27.80(12) 2_775 2_775 ? O3 Na2 C18 122.16(15) 2_775 2_775 ? O1S Na2 C18 113.51(15) . 2_775 ? O7 Na2 C18 28.07(12) 2_775 2_775 ? O1 Na2 Na1 48.58(9) . . ? O8 Na2 Na1 145.78(12) 2_775 . ? O3 Na2 Na1 51.52(10) 2_775 . ? O1S Na2 Na1 64.00(10) . . ? O7 Na2 Na1 155.54(11) 2_775 . ? C18 Na2 Na1 170.68(13) 2_775 . ? O1 Na2 Na3 43.16(9) . . ? O8 Na2 Na3 149.52(12) 2_775 . ? O3 Na2 Na3 46.71(9) 2_775 . ? O1S Na2 Na3 120.10(11) . . ? O7 Na2 Na3 99.32(10) 2_775 . ? C18 Na2 Na3 126.16(12) 2_775 . ? Na1 Na2 Na3 56.29(5) . . ? O1 Na2 Na3 138.95(11) . 2_775 ? O8 Na2 Na3 41.30(9) 2_775 2_775 ? O3 Na2 Na3 110.76(11) 2_775 2_775 ? O1S Na2 Na3 46.99(10) . 2_775 ? O7 Na2 Na3 97.05(10) 2_775 2_775 ? C18 Na2 Na3 68.99(10) 2_775 2_775 ? Na1 Na2 Na3 105.76(7) . 2_775 ? Na3 Na2 Na3 156.25(7) . 2_775 ? O8 Na3 O13 107.25(19) . . ? O8 Na3 O5 118.03(14) . . ? O13 Na3 O5 79.96(18) . . ? O8 Na3 O1 98.01(13) . . ? O13 Na3 O1 154.45(19) . . ? O5 Na3 O1 84.92(13) . . ? O8 Na3 O3 157.27(13) . 2_775 ? O13 Na3 O3 85.80(18) . 2_775 ? O5 Na3 O3 81.99(13) . 2_775 ? O1 Na3 O3 71.71(11) . 2_775 ? O8 Na3 O1S 81.76(12) . 2_774 ? O13 Na3 O1S 96.54(17) . 2_774 ? O5 Na3 O1S 160.13(14) . 2_774 ? O1 Na3 O1S 90.72(12) . 2_774 ? O3 Na3 O1S 78.24(12) 2_775 2_774 ? O8 Na3 Na1 135.87(12) . . ? O13 Na3 Na1 107.66(17) . . ? O5 Na3 Na1 45.22(10) . . ? O1 Na3 Na1 48.42(9) . . ? O3 Na3 Na1 50.72(9) 2_775 . ? O1S Na3 Na1 119.70(10) 2_774 . ? O8 Na3 Na2 119.04(11) . . ? O13 Na3 Na2 124.51(17) . . ? O5 Na3 Na2 101.78(11) . . ? O1 Na3 Na2 39.49(8) . . ? O3 Na3 Na2 41.16(8) 2_775 . ? O1S Na3 Na2 63.95(9) 2_774 . ? Na1 Na3 Na2 56.69(5) . . ? O8 Na3 Na2 40.25(9) . 2_774 ? O13 Na3 Na2 112.96(16) . 2_774 ? O5 Na3 Na2 156.12(13) . 2_774 ? O1 Na3 Na2 88.79(10) . 2_774 ? O3 Na3 Na2 117.76(10) 2_775 2_774 ? O1S Na3 Na2 42.52(8) 2_774 2_774 ? Na1 Na3 Na2 136.76(7) . 2_774 ? Na2 Na3 Na2 87.53(4) . 2_774 ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.798 _refine_diff_density_min -0.437 _refine_diff_density_rms 0.095