# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dr-arp1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C54 H56 Cu4 N8 O8, Na, Cl O4' _chemical_formula_sum 'C54 H56 Cl Cu4 N8 Na O12' _chemical_formula_weight 1321.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 35.6139(6) _cell_length_b 35.6139(6) _cell_length_c 11.47320(10) _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 120.0000 _cell_volume 12602.4(3) _cell_formula_units_Z 9 _cell_measurement_temperature 295 _cell_measurement_reflns_used 27793 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 27.50 _exptl_crystal_description prismatic _exptl_crystal_colour green _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6084 _exptl_absorpt_coefficient_mu 1.622 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.653 _exptl_absorpt_correction_T_max 0.764 _exptl_absorpt_process_details 'SORTAV (R.H.Blessing, Acta Crystallogr., 1995, A51, 33)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27723 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -46 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.38 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6398 _reflns_number_gt 5018 _reflns_threshold_expression I>2sigma(I) _computing_data_collection 'COLLECT (Nonius, 1997)' _computing_cell_refinement 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997), PARST (Nardelli, 1995), PLATON (Spek, 2009)' _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^)+(0.0713P)^2^+36.8216P] 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 6398 _refine_ls_number_parameters 379 _refine_ls_number_restraints 42 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1356 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.043 _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 0.439990(12) -0.493066(13) 0.22059(3) 0.03931(13) Uani 1 1 d . . . Cu2 Cu 0.438499(12) -0.451746(13) -0.00777(3) 0.04045(13) Uani 1 1 d . . . Na1 Na 0.5000 -0.5000 0.0000 0.0452(4) Uani 1 2 d S . . O1 O 0.49714(7) -0.48689(8) 0.22366(19) 0.0455(5) Uani 1 1 d . . . O2 O 0.42901(6) -0.51580(7) 0.02385(17) 0.0371(4) Uani 1 1 d . . . O3 O 0.49599(7) -0.43214(8) -0.06498(19) 0.0454(5) Uani 1 1 d . . . O4 O 0.46238(8) -0.43603(8) 0.15652(19) 0.0457(5) Uani 1 1 d . . . H4O H 0.4899(15) -0.4258(14) 0.151(4) 0.064(13) Uiso 1 1 d . . . N1 N 0.41588(8) -0.54346(9) 0.3190(2) 0.0447(6) Uani 1 1 d . . . N2 N 0.37602(9) -0.50252(10) 0.2243(2) 0.0468(6) Uani 1 1 d . . . N3 N 0.37471(9) -0.47447(9) 0.0453(2) 0.0446(6) Uani 1 1 d . . . N4 N 0.42233(9) -0.42761(9) -0.1370(2) 0.0463(6) Uani 1 1 d . . . C1 C 0.51107(10) -0.50363(10) 0.3029(2) 0.0397(6) Uani 1 1 d . . . C2 C 0.55543(11) -0.49064(12) 0.3073(3) 0.0503(8) Uani 1 1 d . . . H2 H 0.5743 -0.4702 0.2541 0.060 Uiso 1 1 calc R . . C3 C 0.57167(12) -0.50743(12) 0.3883(3) 0.0534(8) Uani 1 1 d . . . H3 H 0.6012 -0.4980 0.3887 0.064 Uiso 1 1 calc R . . C4 C 0.54482(13) -0.53811(12) 0.4691(3) 0.0537(8) Uani 1 1 d . . . H4 H 0.5560 -0.5494 0.5233 0.064 Uiso 1 1 calc R . . C5 C 0.50173(12) -0.55135(11) 0.4674(3) 0.0481(8) Uani 1 1 d . . . H5 H 0.4836 -0.5716 0.5221 0.058 Uiso 1 1 calc R . . C6 C 0.48381(10) -0.53548(10) 0.3859(3) 0.0403(7) Uani 1 1 d . . . C7 C 0.43737(11) -0.55414(10) 0.3859(3) 0.0439(7) Uani 1 1 d . . . H7 H 0.4217 -0.5760 0.4399 0.053 Uiso 1 1 calc R . . C8 C 0.36852(11) -0.56734(13) 0.3220(3) 0.0567(9) Uani 1 1 d . . . H8A H 0.3584 -0.5844 0.3928 0.068 Uiso 1 1 calc R . . H8B H 0.3572 -0.5868 0.2558 0.068 Uiso 1 1 calc R . . C9 C 0.35326(12) -0.53499(15) 0.3179(3) 0.0601(10) Uani 1 1 d . . . H9A H 0.3223 -0.5499 0.3037 0.072 Uiso 1 1 calc R . . H9B H 0.3587 -0.5203 0.3925 0.072 Uiso 1 1 calc R . . C10 C 0.37591(15) -0.46134(15) 0.2499(3) 0.0645(10) Uani 1 1 d . . . H10A H 0.4019 -0.4412 0.2922 0.077 Uiso 1 1 calc R . . H10B H 0.3507 -0.4671 0.2959 0.077 Uiso 1 1 calc R . . C11 C 0.37455(14) -0.44295(14) 0.1309(4) 0.0623(10) Uani 1 1 d . . . H11A H 0.3485 -0.4409 0.1227 0.075 Uiso 1 1 calc R . . H11B H 0.3997 -0.4144 0.1200 0.075 Uiso 1 1 calc R . . C12 C 0.35299(10) -0.51575(11) 0.1103(3) 0.0425(7) Uani 1 1 d . . . H12 H 0.3229 -0.5231 0.1237 0.051 Uiso 1 1 calc R . . C13 C 0.35218(9) -0.55361(10) 0.0484(2) 0.0395(6) Uani 1 1 d . . . C14 C 0.31251(10) -0.59170(12) 0.0326(3) 0.0480(8) Uani 1 1 d . . . H14 H 0.2873 -0.5933 0.0611 0.058 Uiso 1 1 calc R . . C15 C 0.30991(11) -0.62683(12) -0.0241(3) 0.0523(8) Uani 1 1 d . . . H15 H 0.2835 -0.6524 -0.0313 0.063 Uiso 1 1 calc R . . C16 C 0.34750(12) -0.62351(11) -0.0705(3) 0.0493(8) Uani 1 1 d . . . H16 H 0.3459 -0.6467 -0.1120 0.059 Uiso 1 1 calc R . . C17 C 0.38686(10) -0.58654(10) -0.0559(3) 0.0401(6) Uani 1 1 d . . . H17 H 0.4115 -0.5852 -0.0876 0.048 Uiso 1 1 calc R . . C18 C 0.39084(9) -0.55047(10) 0.0060(2) 0.0347(6) Uani 1 1 d . . . C19 C 0.35140(11) -0.47706(13) -0.0644(3) 0.0539(9) Uani 1 1 d . . . H19A H 0.3232 -0.4805 -0.0465 0.065 Uiso 1 1 calc R . . H19B H 0.3470 -0.5020 -0.1095 0.065 Uiso 1 1 calc R . . C20 C 0.37773(12) -0.43627(14) -0.1336(4) 0.0598(10) Uani 1 1 d . . . H20A H 0.3663 -0.4399 -0.2120 0.072 Uiso 1 1 calc R . . H20B H 0.3767 -0.4122 -0.0972 0.072 Uiso 1 1 calc R . . C21 C 0.51475(10) -0.40526(10) -0.1523(3) 0.0390(6) Uani 1 1 d . . . C22 C 0.55908(11) -0.38937(11) -0.1738(3) 0.0466(7) Uani 1 1 d . . . H22 H 0.5743 -0.3982 -0.1259 0.056 Uiso 1 1 calc R . . C23 C 0.58056(12) -0.36105(11) -0.2639(3) 0.0530(9) Uani 1 1 d . . . H23 H 0.6099 -0.3510 -0.2752 0.064 Uiso 1 1 calc R . . C24 C 0.55892(14) -0.34738(12) -0.3381(3) 0.0593(10) Uani 1 1 d . . . H24 H 0.5734 -0.3285 -0.3994 0.071 Uiso 1 1 calc R . . C25 C 0.51629(14) -0.36210(12) -0.3194(3) 0.0566(9) Uani 1 1 d . . . H25 H 0.5017 -0.3530 -0.3689 0.068 Uiso 1 1 calc R . . C26 C 0.49309(11) -0.39074(10) -0.2277(3) 0.0431(7) Uani 1 1 d . . . C27 C 0.44795(12) -0.40372(12) -0.2181(3) 0.0498(8) Uani 1 1 d . . . H27 H 0.4364 -0.3940 -0.2753 0.060 Uiso 1 1 calc R . . Cl1 Cl 0.26773(12) -0.43267(12) -0.1782(4) 0.1247(12) Uani 0.50 1 d PD . . O1A O 0.2264(5) -0.4515(5) -0.2130(17) 0.173(6) Uiso 0.20 1 d PD A 1 O2A O 0.2792(6) -0.4629(6) -0.1650(18) 0.173(6) Uiso 0.20 1 d PD A 1 O3A O 0.2721(6) -0.4125(6) -0.0765(15) 0.173(6) Uiso 0.20 1 d PD A 1 O4A O 0.2932(6) -0.4038(6) -0.2583(15) 0.173(6) Uiso 0.20 1 d PD A 1 O1B O 0.2263(4) -0.4763(4) -0.1862(13) 0.185(5) Uiso 0.30 1 d PD A 2 O2B O 0.3015(4) -0.4322(5) -0.2601(13) 0.185(5) Uiso 0.30 1 d PD A 2 O3B O 0.2848(5) -0.4252(5) -0.0540(11) 0.185(5) Uiso 0.30 1 d PD A 2 O4B O 0.2584(5) -0.3970(5) -0.2127(14) 0.185(5) Uiso 0.30 1 d PD A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0352(2) 0.0449(2) 0.03138(19) -0.00118(14) 0.00265(13) 0.01517(17) Cu2 0.0370(2) 0.0471(2) 0.0381(2) 0.00239(15) 0.00060(14) 0.02160(18) Na1 0.0293(8) 0.0503(10) 0.0510(10) 0.0008(8) 0.0048(7) 0.0162(8) O1 0.0370(11) 0.0541(13) 0.0404(11) 0.0077(10) 0.0039(9) 0.0191(10) O2 0.0274(10) 0.0401(11) 0.0392(10) -0.0035(8) 0.0009(8) 0.0134(9) O3 0.0400(12) 0.0549(14) 0.0398(11) 0.0079(9) 0.0032(9) 0.0227(11) O4 0.0469(14) 0.0438(12) 0.0394(11) -0.0058(9) -0.0052(10) 0.0174(11) N1 0.0368(14) 0.0483(15) 0.0371(13) 0.0013(11) 0.0062(10) 0.0124(12) N2 0.0427(15) 0.0621(18) 0.0360(13) -0.0048(12) 0.0054(11) 0.0266(14) N3 0.0401(14) 0.0541(16) 0.0435(14) -0.0045(12) -0.0004(11) 0.0266(13) N4 0.0431(15) 0.0488(16) 0.0489(15) 0.0047(12) -0.0032(12) 0.0245(13) C1 0.0397(16) 0.0402(16) 0.0336(14) -0.0025(12) -0.0023(12) 0.0157(13) C2 0.0418(18) 0.051(2) 0.0465(18) 0.0070(14) 0.0016(14) 0.0151(16) C3 0.0430(18) 0.055(2) 0.058(2) -0.0024(16) -0.0075(15) 0.0206(16) C4 0.059(2) 0.052(2) 0.0483(18) -0.0030(15) -0.0145(16) 0.0265(18) C5 0.058(2) 0.0407(17) 0.0363(15) -0.0006(12) -0.0024(14) 0.0177(16) C6 0.0451(17) 0.0370(15) 0.0329(14) -0.0043(11) 0.0005(12) 0.0162(14) C7 0.0498(18) 0.0400(16) 0.0316(14) 0.0006(12) 0.0071(13) 0.0147(14) C8 0.0389(18) 0.067(2) 0.0450(18) 0.0123(16) 0.0103(14) 0.0117(17) C9 0.0449(19) 0.092(3) 0.0381(17) 0.0034(17) 0.0129(14) 0.031(2) C10 0.068(3) 0.080(3) 0.057(2) -0.0218(19) 0.0017(18) 0.046(2) C11 0.063(2) 0.066(2) 0.069(2) -0.0123(19) 0.0043(19) 0.042(2) C12 0.0322(15) 0.0561(19) 0.0410(15) -0.0030(13) 0.0048(12) 0.0233(14) C13 0.0323(15) 0.0477(17) 0.0337(14) -0.0001(12) 0.0008(11) 0.0165(13) C14 0.0312(15) 0.059(2) 0.0454(17) 0.0027(15) 0.0014(12) 0.0159(15) C15 0.0400(18) 0.0452(18) 0.0531(19) 0.0037(15) -0.0085(14) 0.0073(15) C16 0.054(2) 0.0416(18) 0.0473(17) -0.0030(14) -0.0070(15) 0.0198(16) C17 0.0403(16) 0.0397(16) 0.0395(15) 0.0026(12) 0.0005(12) 0.0194(13) C18 0.0305(14) 0.0418(15) 0.0273(12) 0.0014(11) -0.0010(10) 0.0146(12) C19 0.0382(18) 0.068(2) 0.058(2) 0.0041(17) -0.0047(15) 0.0281(17) C20 0.049(2) 0.071(3) 0.067(2) 0.0112(19) -0.0032(17) 0.035(2) C21 0.0421(16) 0.0332(15) 0.0347(14) -0.0046(11) -0.0005(12) 0.0137(13) C22 0.0433(17) 0.0457(18) 0.0435(17) -0.0075(13) -0.0016(13) 0.0168(15) C23 0.0470(19) 0.0402(18) 0.0541(19) -0.0078(14) 0.0075(15) 0.0085(15) C24 0.066(2) 0.0385(18) 0.059(2) 0.0069(15) 0.0181(18) 0.0154(17) C25 0.072(3) 0.0440(19) 0.052(2) 0.0089(15) 0.0051(17) 0.0281(19) C26 0.0501(18) 0.0370(16) 0.0399(15) -0.0003(12) 0.0004(13) 0.0201(14) C27 0.059(2) 0.051(2) 0.0444(17) 0.0054(14) -0.0045(15) 0.0319(17) Cl1 0.116(3) 0.119(3) 0.152(3) 0.039(2) 0.040(2) 0.068(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.919(2) . ? Cu1 N1 1.921(3) . ? Cu1 O1 1.935(2) . ? Cu1 N2 2.130(3) . ? Cu1 O2 2.364(2) . ? Cu1 Cu2 3.0184(5) . ? Cu1 Na1 3.4003(4) . ? Cu2 O3 1.919(2) . ? Cu2 N4 1.940(3) . ? Cu2 O4 2.028(2) . ? Cu2 N3 2.085(3) . ? Cu2 O2 2.163(2) . ? Cu2 Na1 3.3945(4) . ? Na1 O2 2.3153(19) . ? Na1 O2 2.3153(19) 10_645 ? Na1 O3 2.601(2) . ? Na1 O3 2.601(2) 10_645 ? Na1 O1 2.619(2) . ? Na1 O1 2.619(2) 10_645 ? Na1 Cu2 3.3945(4) 10_645 ? Na1 Cu1 3.4003(4) 10_645 ? O1 C1 1.314(4) . ? O2 C18 1.318(3) . ? O3 C21 1.314(4) . ? O4 H4O 0.86(5) . ? N1 C7 1.269(4) . ? N1 C8 1.461(4) . ? N2 C9 1.487(5) . ? N2 C12 1.489(4) . ? N2 C10 1.498(5) . ? N3 C12 1.476(4) . ? N3 C19 1.484(4) . ? N3 C11 1.494(4) . ? N4 C27 1.282(4) . ? N4 C20 1.459(5) . ? C1 C2 1.407(5) . ? C1 C6 1.426(4) . ? C2 C3 1.379(5) . ? C2 H2 0.9300 . ? C3 C4 1.387(5) . ? C3 H3 0.9300 . ? C4 C5 1.362(5) . ? C4 H4 0.9300 . ? C5 C6 1.401(5) . ? C5 H5 0.9300 . ? C6 C7 1.441(5) . ? C7 H7 0.9300 . ? C8 C9 1.501(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.525(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.512(5) . ? C12 H12 0.9800 . ? C13 C14 1.397(4) . ? C13 C18 1.411(4) . ? C14 C15 1.371(5) . ? C14 H14 0.9300 . ? C15 C16 1.390(5) . ? C15 H15 0.9300 . ? C16 C17 1.372(5) . ? C16 H16 0.9300 . ? C17 C18 1.412(4) . ? C17 H17 0.9300 . ? C19 C20 1.503(5) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.407(5) . ? C21 C26 1.417(5) . ? C22 C23 1.378(5) . ? C22 H22 0.9300 . ? C23 C24 1.390(6) . ? C23 H23 0.9300 . ? C24 C25 1.353(6) . ? C24 H24 0.9300 . ? C25 C26 1.410(5) . ? C25 H25 0.9300 . ? C26 C27 1.438(5) . ? C27 H27 0.9300 . ? Cl1 O2A 1.338(14) . ? Cl1 O4A 1.338(14) . ? Cl1 O3A 1.338(14) . ? Cl1 O1A 1.338(14) . ? Cl1 O4B 1.519(12) . ? Cl1 O1B 1.519(12) . ? Cl1 O3B 1.519(12) . ? Cl1 O2B 1.520(12) . ? 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 N1 165.68(11) . . ? O4 Cu1 O1 91.71(11) . . ? N1 Cu1 O1 92.80(11) . . ? O4 Cu1 N2 91.17(12) . . ? N1 Cu1 N2 84.12(12) . . ? O1 Cu1 N2 176.90(11) . . ? O4 Cu1 O2 84.65(8) . . ? N1 Cu1 O2 108.72(10) . . ? O1 Cu1 O2 92.34(8) . . ? N2 Cu1 O2 89.08(9) . . ? O4 Cu1 Cu2 41.47(7) . . ? N1 Cu1 Cu2 148.96(8) . . ? O1 Cu1 Cu2 103.55(6) . . ? N2 Cu1 Cu2 79.40(8) . . ? O2 Cu1 Cu2 45.40(5) . . ? O4 Cu1 Na1 81.27(7) . . ? N1 Cu1 Na1 111.90(8) . . ? O1 Cu1 Na1 50.08(6) . . ? N2 Cu1 Na1 131.65(7) . . ? O2 Cu1 Na1 42.83(5) . . ? Cu2 Cu1 Na1 63.527(10) . . ? O3 Cu2 N4 94.38(11) . . ? O3 Cu2 O4 89.64(10) . . ? N4 Cu2 O4 139.86(11) . . ? O3 Cu2 N3 176.82(10) . . ? N4 Cu2 N3 83.56(11) . . ? O4 Cu2 N3 93.50(11) . . ? O3 Cu2 O2 90.96(9) . . ? N4 Cu2 O2 132.13(10) . . ? O4 Cu2 O2 87.60(9) . . ? N3 Cu2 O2 88.65(9) . . ? O3 Cu2 Cu1 101.46(7) . . ? N4 Cu2 Cu1 163.92(9) . . ? O4 Cu2 Cu1 38.80(7) . . ? N3 Cu2 Cu1 80.73(8) . . ? O2 Cu2 Cu1 51.09(5) . . ? O3 Cu2 Na1 49.61(7) . . ? N4 Cu2 Na1 130.83(9) . . ? O4 Cu2 Na1 80.08(7) . . ? N3 Cu2 Na1 130.50(8) . . ? O2 Cu2 Na1 42.42(5) . . ? Cu1 Cu2 Na1 63.725(10) . . ? O2 Na1 O2 180.0 . 10_645 ? O2 Na1 O3 72.48(7) . . ? O2 Na1 O3 107.52(7) 10_645 . ? O2 Na1 O3 107.52(7) . 10_645 ? O2 Na1 O3 72.48(7) 10_645 10_645 ? O3 Na1 O3 180.00(10) . 10_645 ? O2 Na1 O1 78.02(7) . . ? O2 Na1 O1 101.98(7) 10_645 . ? O3 Na1 O1 95.17(7) . . ? O3 Na1 O1 84.83(7) 10_645 . ? O2 Na1 O1 101.98(7) . 10_645 ? O2 Na1 O1 78.02(7) 10_645 10_645 ? O3 Na1 O1 84.83(7) . 10_645 ? O3 Na1 O1 95.17(7) 10_645 10_645 ? O1 Na1 O1 180.00(12) . 10_645 ? O2 Na1 Cu2 39.06(5) . . ? O2 Na1 Cu2 140.94(5) 10_645 . ? O3 Na1 Cu2 34.19(5) . . ? O3 Na1 Cu2 145.81(5) 10_645 . ? O1 Na1 Cu2 80.97(5) . . ? O1 Na1 Cu2 99.03(5) 10_645 . ? O2 Na1 Cu2 140.94(5) . 10_645 ? O2 Na1 Cu2 39.06(5) 10_645 10_645 ? O3 Na1 Cu2 145.81(5) . 10_645 ? O3 Na1 Cu2 34.19(5) 10_645 10_645 ? O1 Na1 Cu2 99.03(5) . 10_645 ? O1 Na1 Cu2 80.97(5) 10_645 10_645 ? Cu2 Na1 Cu2 180.0 . 10_645 ? O2 Na1 Cu1 43.95(5) . . ? O2 Na1 Cu1 136.05(5) 10_645 . ? O3 Na1 Cu1 79.47(5) . . ? O3 Na1 Cu1 100.53(5) 10_645 . ? O1 Na1 Cu1 34.51(5) . . ? O1 Na1 Cu1 145.49(5) 10_645 . ? Cu2 Na1 Cu1 52.748(9) . . ? Cu2 Na1 Cu1 127.252(9) 10_645 . ? O2 Na1 Cu1 136.05(5) . 10_645 ? O2 Na1 Cu1 43.95(5) 10_645 10_645 ? O3 Na1 Cu1 100.53(5) . 10_645 ? O3 Na1 Cu1 79.47(5) 10_645 10_645 ? O1 Na1 Cu1 145.49(5) . 10_645 ? O1 Na1 Cu1 34.51(5) 10_645 10_645 ? Cu2 Na1 Cu1 127.252(9) . 10_645 ? Cu2 Na1 Cu1 52.748(9) 10_645 10_645 ? Cu1 Na1 Cu1 180.000(11) . 10_645 ? C1 O1 Cu1 125.14(19) . . ? C1 O1 Na1 122.70(19) . . ? Cu1 O1 Na1 95.42(8) . . ? C18 O2 Cu2 120.41(18) . . ? C18 O2 Na1 134.35(19) . . ? Cu2 O2 Na1 98.52(8) . . ? C18 O2 Cu1 112.70(16) . . ? Cu2 O2 Cu1 83.51(7) . . ? Na1 O2 Cu1 93.22(7) . . ? C21 O3 Cu2 126.0(2) . . ? C21 O3 Na1 130.6(2) . . ? Cu2 O3 Na1 96.21(9) . . ? Cu1 O4 Cu2 99.73(10) . . ? Cu1 O4 H4O 105(3) . . ? Cu2 O4 H4O 106(3) . . ? C7 N1 C8 120.3(3) . . ? C7 N1 Cu1 125.5(2) . . ? C8 N1 Cu1 113.8(2) . . ? C9 N2 C12 112.9(3) . . ? C9 N2 C10 110.6(3) . . ? C12 N2 C10 102.2(3) . . ? C9 N2 Cu1 105.2(2) . . ? C12 N2 Cu1 114.15(18) . . ? C10 N2 Cu1 112.0(2) . . ? C12 N3 C19 111.6(3) . . ? C12 N3 C11 102.6(3) . . ? C19 N3 C11 113.1(3) . . ? C12 N3 Cu2 117.43(19) . . ? C19 N3 Cu2 104.1(2) . . ? C11 N3 Cu2 108.2(2) . . ? C27 N4 C20 119.9(3) . . ? C27 N4 Cu2 125.3(2) . . ? C20 N4 Cu2 114.7(2) . . ? O1 C1 C2 119.5(3) . . ? O1 C1 C6 124.2(3) . . ? C2 C1 C6 116.4(3) . . ? C3 C2 C1 121.8(3) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C2 C3 C4 121.3(3) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 118.5(3) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? C4 C5 C6 122.1(3) . . ? C4 C5 H5 118.9 . . ? C6 C5 H5 118.9 . . ? C5 C6 C1 120.0(3) . . ? C5 C6 C7 117.6(3) . . ? C1 C6 C7 122.3(3) . . ? N1 C7 C6 125.9(3) . . ? N1 C7 H7 117.1 . . ? C6 C7 H7 117.1 . . ? N1 C8 C9 108.0(3) . . ? N1 C8 H8A 110.1 . . ? C9 C8 H8A 110.1 . . ? N1 C8 H8B 110.1 . . ? C9 C8 H8B 110.1 . . ? H8A C8 H8B 108.4 . . ? N2 C9 C8 110.7(3) . . ? N2 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N2 C10 C11 105.1(3) . . ? N2 C10 H10A 110.7 . . ? C11 C10 H10A 110.7 . . ? N2 C10 H10B 110.7 . . ? C11 C10 H10B 110.7 . . ? H10A C10 H10B 108.8 . . ? N3 C11 C10 104.6(3) . . ? N3 C11 H11A 110.8 . . ? C10 C11 H11A 110.8 . . ? N3 C11 H11B 110.8 . . ? C10 C11 H11B 110.8 . . ? H11A C11 H11B 108.9 . . ? N3 C12 N2 101.4(3) . . ? N3 C12 C13 114.7(2) . . ? N2 C12 C13 117.2(3) . . ? N3 C12 H12 107.7 . . ? N2 C12 H12 107.7 . . ? C13 C12 H12 107.7 . . ? C14 C13 C18 120.4(3) . . ? C14 C13 C12 119.1(3) . . ? C18 C13 C12 120.6(3) . . ? C15 C14 C13 121.4(3) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C14 C15 C16 118.8(3) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 120.9(3) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C16 C17 C18 121.6(3) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? O2 C18 C13 122.0(3) . . ? O2 C18 C17 121.2(3) . . ? C13 C18 C17 116.8(3) . . ? N3 C19 C20 109.2(3) . . ? N3 C19 H19A 109.8 . . ? C20 C19 H19A 109.8 . . ? N3 C19 H19B 109.8 . . ? C20 C19 H19B 109.8 . . ? H19A C19 H19B 108.3 . . ? N4 C20 C19 107.8(3) . . ? N4 C20 H20A 110.1 . . ? C19 C20 H20A 110.1 . . ? N4 C20 H20B 110.1 . . ? C19 C20 H20B 110.1 . . ? H20A C20 H20B 108.5 . . ? O3 C21 C22 119.1(3) . . ? O3 C21 C26 124.0(3) . . ? C22 C21 C26 116.9(3) . . ? C23 C22 C21 121.7(3) . . ? C23 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C23 C24 120.9(4) . . ? C22 C23 H23 119.5 . . ? C24 C23 H23 119.5 . . ? C25 C24 C23 118.6(3) . . ? C25 C24 H24 120.7 . . ? C23 C24 H24 120.7 . . ? C24 C25 C26 122.5(4) . . ? C24 C25 H25 118.8 . . ? C26 C25 H25 118.8 . . ? C25 C26 C21 119.4(3) . . ? C25 C26 C27 116.5(3) . . ? C21 C26 C27 124.1(3) . . ? N4 C27 C26 125.4(3) . . ? N4 C27 H27 117.3 . . ? C26 C27 H27 117.3 . . ? O2A Cl1 O4A 109.47(7) . . ? O2A Cl1 O3A 109.48(7) . . ? O4A Cl1 O3A 109.47(7) . . ? O2A Cl1 O1A 109.47(7) . . ? O4A Cl1 O1A 109.47(7) . . ? O3A Cl1 O1A 109.47(7) . . ? O2A Cl1 O4B 170.5(9) . . ? O4A Cl1 O4B 61.7(9) . . ? O3A Cl1 O4B 78.0(9) . . ? O1A Cl1 O4B 72.3(9) . . ? O2A Cl1 O1B 73.4(9) . . ? O4A Cl1 O1B 133.1(11) . . ? O3A Cl1 O1B 113.3(11) . . ? O1A Cl1 O1B 37.5(9) . . ? O4B Cl1 O1B 109.49(6) . . ? O2A Cl1 O3B 77.2(9) . . ? O4A Cl1 O3B 116.9(11) . . ? O3A Cl1 O3B 32.8(9) . . ? O1A Cl1 O3B 127.6(11) . . ? O4B Cl1 O3B 109.48(6) . . ? O1B Cl1 O3B 109.50(6) . . ? O2A Cl1 O2B 61.3(9) . . ? O4A Cl1 O2B 48.6(9) . . ? O3A Cl1 O2B 130.8(11) . . ? O1A Cl1 O2B 119.2(11) . . ? O4B Cl1 O2B 109.45(6) . . ? O1B Cl1 O2B 109.46(6) . . ? O3B Cl1 O2B 109.46(6) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.798 _refine_diff_density_min -0.614 _refine_diff_density_rms 0.076 _database_code_depnum_ccdc_archive 'CCDC 651162' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_drab07 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C51 H76 Cu2 N4 O4,1.5(H2 O)' _chemical_formula_sum 'C51 H79 Cu2 N4 O5.50' _chemical_formula_weight 963.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 23.2607(12) _cell_length_b 19.7554(10) _cell_length_c 28.1663(14) _cell_angle_alpha 90.00 _cell_angle_beta 101.9139(15) _cell_angle_gamma 90.00 _cell_volume 12664.3(11) _cell_formula_units_Z 8 _cell_measurement_temperature 295 _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.010 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4120 _exptl_absorpt_coefficient_mu 0.711 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.812 _exptl_absorpt_correction_T_max 0.897 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295 _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 'BRUCKER APEX II CCD' _diffrn_measurement_method '\f scans and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 73482 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 11138 _reflns_number_gt 6417 _reflns_threshold_expression I>2sigma(I) _computing_data_collection Brucker _computing_cell_refinement Brucker _computing_data_reduction Brucker _computing_structure_solution 'SHELXS-86 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Diamond _computing_publication_material 'SHELXL-97 (Sheldrick, 1997), PLATON (Spek, 2009)' _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^)+(0.1194P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11138 _refine_ls_number_parameters 561 _refine_ls_number_restraints 64 _refine_ls_R_factor_all 0.1052 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.2023 _refine_ls_wR_factor_gt 0.1873 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_restrained_S_all 0.990 _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 0.01846(2) 0.38476(3) 0.040322(19) 0.05355(19) Uani 1 1 d . . . Cu2 Cu 0.02958(2) 0.31106(3) 0.13552(2) 0.0630(2) Uani 1 1 d . . . O1 O 0.09628(11) 0.39614(15) 0.02963(10) 0.0559(8) Uani 1 1 d . . . O2 O 0.09801(15) 0.31648(16) 0.18602(12) 0.0786(10) Uani 1 1 d . . . O3 O 0.01917(11) 0.27858(14) 0.06348(10) 0.0505(7) Uani 1 1 d . . . O4 O 0.04723(13) 0.39824(14) 0.11007(11) 0.0569(8) Uani 1 1 d D . . H4 H 0.0880(10) 0.403(2) 0.1087(17) 0.086(16) Uiso 1 1 d D . . N1 N -0.01419(15) 0.3844(2) -0.02824(14) 0.0649(11) Uani 1 1 d . . . N2 N -0.07094(15) 0.39221(18) 0.04695(15) 0.0598(10) Uani 1 1 d . . . N3 N -0.06956(16) 0.33057(19) 0.11573(15) 0.0653(10) Uani 1 1 d . . . N4 N 0.00355(18) 0.2309(2) 0.16433(15) 0.0703(11) Uani 1 1 d . . . C1 C 0.1232(2) 0.2703(3) 0.21630(17) 0.0671(13) Uani 1 1 d . . . C2 C 0.1797(2) 0.2797(3) 0.24536(16) 0.0694(13) Uani 1 1 d . . . C3 C 0.2045(2) 0.2274(3) 0.27559(17) 0.0788(15) Uani 1 1 d . . . H3 H 0.2420 0.2339 0.2942 0.095 Uiso 1 1 calc R . . C4 C 0.1765(3) 0.1653(3) 0.27988(19) 0.0801(16) Uani 1 1 d . A . C5 C 0.1230(3) 0.1568(3) 0.2527(2) 0.0822(15) Uani 1 1 d . . . H5 H 0.1037 0.1161 0.2550 0.099 Uiso 1 1 calc R . . C6 C 0.0942(2) 0.2066(3) 0.22047(18) 0.0721(14) Uani 1 1 d . . . C7 C 0.2121(2) 0.3463(3) 0.24380(17) 0.0750(14) Uani 1 1 d . . . C8 C 0.2730(3) 0.3462(4) 0.2772(2) 0.139(3) Uani 1 1 d . . . H8A H 0.2701 0.3288 0.3084 0.208 Uiso 1 1 calc R . . H8B H 0.2880 0.3916 0.2808 0.208 Uiso 1 1 calc R . . H8C H 0.2990 0.3183 0.2634 0.208 Uiso 1 1 calc R . . C9 C 0.2229(3) 0.3584(3) 0.19273(19) 0.0977(18) Uani 1 1 d . . . H9A H 0.2460 0.3220 0.1840 0.147 Uiso 1 1 calc R . . H9B H 0.2436 0.4004 0.1921 0.147 Uiso 1 1 calc R . . H9C H 0.1860 0.3606 0.1701 0.147 Uiso 1 1 calc R . . C10 C 0.1762(3) 0.4045(3) 0.2590(2) 0.115(2) Uani 1 1 d . . . H10A H 0.1379 0.4054 0.2382 0.172 Uiso 1 1 calc R . . H10B H 0.1959 0.4466 0.2565 0.172 Uiso 1 1 calc R . . H10C H 0.1723 0.3978 0.2920 0.172 Uiso 1 1 calc R . . C11 C 0.2093(2) 0.1092(3) 0.31499(18) 0.0944(18) Uani 1 1 d D . . C12 C 0.2658(3) 0.0934(5) 0.3006(3) 0.1163(19) Uiso 0.70 1 d PD A 1 H12A H 0.2831 0.0539 0.3178 0.174 Uiso 0.70 1 calc PR A 1 H12B H 0.2922 0.1311 0.3084 0.174 Uiso 0.70 1 calc PR A 1 H12C H 0.2588 0.0850 0.2663 0.174 Uiso 0.70 1 calc PR A 1 C13 C 0.2219(4) 0.1334(5) 0.3661(3) 0.1163(19) Uiso 0.70 1 d PD A 1 H13A H 0.2403 0.0978 0.3871 0.174 Uiso 0.70 1 calc PR A 1 H13B H 0.1858 0.1462 0.3752 0.174 Uiso 0.70 1 calc PR A 1 H13C H 0.2477 0.1718 0.3691 0.174 Uiso 0.70 1 calc PR A 1 C14 C 0.1737(4) 0.0461(4) 0.3119(3) 0.1163(19) Uiso 0.70 1 d PD A 1 H14A H 0.1680 0.0280 0.2797 0.174 Uiso 0.70 1 calc PR A 1 H14B H 0.1362 0.0562 0.3195 0.174 Uiso 0.70 1 calc PR A 1 H14C H 0.1939 0.0135 0.3346 0.174 Uiso 0.70 1 calc PR A 1 C12' C 0.2338(8) 0.0560(9) 0.2874(8) 0.150(6) Uiso 0.30 1 d PD A 2 H12D H 0.2540 0.0770 0.2648 0.225 Uiso 0.30 1 calc PR A 2 H12E H 0.2024 0.0284 0.2701 0.225 Uiso 0.30 1 calc PR A 2 H12F H 0.2607 0.0283 0.3095 0.225 Uiso 0.30 1 calc PR A 2 C13' C 0.2592(6) 0.1364(13) 0.3518(6) 0.150(6) Uiso 0.30 1 d PD A 2 H13D H 0.2530 0.1836 0.3568 0.225 Uiso 0.30 1 calc PR A 2 H13E H 0.2951 0.1305 0.3405 0.225 Uiso 0.30 1 calc PR A 2 H13F H 0.2618 0.1124 0.3818 0.225 Uiso 0.30 1 calc PR A 2 C14' C 0.1693(10) 0.0744(11) 0.3422(7) 0.150(6) Uiso 0.30 1 d PD A 2 H14D H 0.1893 0.0365 0.3595 0.225 Uiso 0.30 1 calc PR A 2 H14E H 0.1350 0.0588 0.3198 0.225 Uiso 0.30 1 calc PR A 2 H14F H 0.1578 0.1055 0.3647 0.225 Uiso 0.30 1 calc PR A 2 C15 C 0.0348(3) 0.1945(3) 0.1969(2) 0.0778(15) Uani 1 1 d . . . H15 H 0.0170 0.1560 0.2063 0.093 Uiso 1 1 calc R . . C16 C -0.0585(2) 0.2139(3) 0.1464(2) 0.0859(17) Uani 1 1 d . . . H16A H -0.0714 0.1818 0.1682 0.103 Uiso 1 1 calc R . . H16B H -0.0640 0.1935 0.1145 0.103 Uiso 1 1 calc R . . C17 C -0.0935(2) 0.2777(3) 0.1441(2) 0.0810(15) Uani 1 1 d . . . H17A H -0.1341 0.2686 0.1289 0.097 Uiso 1 1 calc R . . H17B H -0.0925 0.2942 0.1767 0.097 Uiso 1 1 calc R . . C18 C -0.0838(2) 0.4001(3) 0.1290(2) 0.0829(16) Uani 1 1 d . . . H18A H -0.0560 0.4156 0.1575 0.099 Uiso 1 1 calc R . . H18B H -0.1231 0.4021 0.1355 0.099 Uiso 1 1 calc R . . C19 C -0.0796(2) 0.4419(2) 0.0857(2) 0.0799(16) Uani 1 1 d . . . H19A H -0.0467 0.4730 0.0933 0.096 Uiso 1 1 calc R . . H19B H -0.1153 0.4679 0.0750 0.096 Uiso 1 1 calc R . . C20 C -0.1021(2) 0.4149(3) -0.0017(2) 0.0826(16) Uani 1 1 d . . . H20A H -0.0976 0.4635 -0.0043 0.099 Uiso 1 1 calc R . . H20B H -0.1437 0.4052 -0.0056 0.099 Uiso 1 1 calc R . . C21 C -0.0790(2) 0.3807(3) -0.0417(2) 0.0825(17) Uani 1 1 d . . . H21A H -0.0918 0.3338 -0.0448 0.099 Uiso 1 1 calc R . . H21B H -0.0933 0.4035 -0.0723 0.099 Uiso 1 1 calc R . . C22 C 0.0152(2) 0.3847(2) -0.06198(18) 0.0673(13) Uani 1 1 d . . . H22 H -0.0067 0.3835 -0.0936 0.081 Uiso 1 1 calc R . . C23 C 0.07714(18) 0.3865(2) -0.05684(15) 0.0511(10) Uani 1 1 d . . . C24 C 0.11513(18) 0.3909(2) -0.01130(16) 0.0502(10) Uani 1 1 d . . . C25 C 0.17684(18) 0.3895(2) -0.00964(16) 0.0526(10) Uani 1 1 d . . . C26 C 0.1950(2) 0.3868(2) -0.05348(18) 0.0632(12) Uani 1 1 d . . . H26 H 0.2352 0.3866 -0.0524 0.076 Uiso 1 1 calc R . . C27 C 0.1577(2) 0.3845(2) -0.09902(18) 0.0657(13) Uani 1 1 d . B . C28 C 0.0992(2) 0.3841(2) -0.09898(17) 0.0637(12) Uani 1 1 d . . . H28 H 0.0727 0.3822 -0.1286 0.076 Uiso 1 1 calc R . . C29 C 0.22090(18) 0.3874(3) 0.03914(17) 0.0642(13) Uani 1 1 d . . . C30 C 0.2104(3) 0.3215(3) 0.06531(19) 0.0819(16) Uani 1 1 d . . . H30A H 0.2399 0.3169 0.0945 0.123 Uiso 1 1 calc R . . H30B H 0.2125 0.2836 0.0444 0.123 Uiso 1 1 calc R . . H30C H 0.1723 0.3230 0.0734 0.123 Uiso 1 1 calc R . . C31 C 0.2145(2) 0.4491(3) 0.06945(18) 0.0751(14) Uani 1 1 d . . . H31A H 0.1746 0.4524 0.0735 0.113 Uiso 1 1 calc R . . H31B H 0.2245 0.4889 0.0534 0.113 Uiso 1 1 calc R . . H31C H 0.2403 0.4449 0.1007 0.113 Uiso 1 1 calc R . . C32 C 0.2839(2) 0.3854(4) 0.0318(2) 0.112(2) Uani 1 1 d . . . H32A H 0.3105 0.3832 0.0628 0.168 Uiso 1 1 calc R . . H32B H 0.2919 0.4254 0.0149 0.168 Uiso 1 1 calc R . . H32C H 0.2892 0.3462 0.0130 0.168 Uiso 1 1 calc R . . C33 C 0.1835(2) 0.3853(2) -0.14549(18) 0.0803(15) Uani 1 1 d D . . C34 C 0.2198(4) 0.3220(4) -0.1489(4) 0.121(4) Uiso 0.60 1 d PD B 3 H34A H 0.2332 0.3224 -0.1789 0.182 Uiso 0.60 1 calc PR B 3 H34B H 0.1960 0.2826 -0.1477 0.182 Uiso 0.60 1 calc PR B 3 H34C H 0.2530 0.3211 -0.1222 0.182 Uiso 0.60 1 calc PR B 3 C35 C 0.1351(4) 0.3899(5) -0.1910(3) 0.119(4) Uiso 0.60 1 d PD B 3 H35A H 0.1524 0.3905 -0.2191 0.178 Uiso 0.60 1 calc PR B 3 H35B H 0.1129 0.4307 -0.1899 0.178 Uiso 0.60 1 calc PR B 3 H35C H 0.1096 0.3515 -0.1925 0.178 Uiso 0.60 1 calc PR B 3 C36 C 0.2232(4) 0.4470(4) -0.1437(4) 0.108(3) Uiso 0.60 1 d PD B 3 H36A H 0.2526 0.4461 -0.1142 0.163 Uiso 0.60 1 calc PR B 3 H36B H 0.2001 0.4874 -0.1445 0.163 Uiso 0.60 1 calc PR B 3 H36C H 0.2418 0.4463 -0.1711 0.163 Uiso 0.60 1 calc PR B 3 C34' C 0.2500(3) 0.3769(7) -0.1350(7) 0.128(6) Uiso 0.40 1 d PD B 4 H34D H 0.2609 0.3391 -0.1136 0.192 Uiso 0.40 1 calc PR B 4 H34E H 0.2682 0.4172 -0.1199 0.192 Uiso 0.40 1 calc PR B 4 H34F H 0.2628 0.3690 -0.1648 0.192 Uiso 0.40 1 calc PR B 4 C35' C 0.1565(7) 0.3238(5) -0.1744(6) 0.144(7) Uiso 0.40 1 d PD B 4 H35D H 0.1738 0.3181 -0.2022 0.216 Uiso 0.40 1 calc PR B 4 H35E H 0.1149 0.3305 -0.1848 0.216 Uiso 0.40 1 calc PR B 4 H35F H 0.1636 0.2842 -0.1543 0.216 Uiso 0.40 1 calc PR B 4 C36' C 0.1681(6) 0.4476(5) -0.1774(5) 0.117(5) Uiso 0.40 1 d PD B 4 H36D H 0.1931 0.4845 -0.1640 0.175 Uiso 0.40 1 calc PR B 4 H36E H 0.1278 0.4597 -0.1787 0.175 Uiso 0.40 1 calc PR B 4 H36F H 0.1736 0.4379 -0.2095 0.175 Uiso 0.40 1 calc PR B 4 C37 C -0.09450(17) 0.3283(2) 0.06328(17) 0.0555(11) Uani 1 1 d . . . H37 H -0.1372 0.3335 0.0589 0.067 Uiso 1 1 calc R . . C38 C -0.08332(17) 0.2652(2) 0.03787(15) 0.0521(10) Uani 1 1 d . . . C39 C -0.02528(16) 0.2428(2) 0.03940(15) 0.0503(10) Uani 1 1 d . . . C40 C -0.01730(17) 0.1821(2) 0.01483(17) 0.0580(12) Uani 1 1 d . . . C41 C -0.06701(19) 0.1475(2) -0.00907(19) 0.0704(14) Uani 1 1 d . . . H41 H -0.0616 0.1075 -0.0249 0.085 Uiso 1 1 calc R . . C42 C -0.12475(18) 0.1694(2) -0.01067(18) 0.0634(12) Uani 1 1 d . C . C43 C -0.13135(17) 0.2278(2) 0.01289(16) 0.0576(11) Uani 1 1 d . . . H43 H -0.1691 0.2436 0.0125 0.069 Uiso 1 1 calc R . . C44 C -0.1780(2) 0.1296(2) -0.03724(18) 0.0827(16) Uani 1 1 d D . . C45 C -0.1612(4) 0.0666(4) -0.0633(3) 0.128(3) Uiso 0.70 1 d PD C 5 H45A H -0.1312 0.0783 -0.0807 0.192 Uiso 0.70 1 calc PR C 5 H45B H -0.1952 0.0500 -0.0856 0.192 Uiso 0.70 1 calc PR C 5 H45C H -0.1467 0.0321 -0.0399 0.192 Uiso 0.70 1 calc PR C 5 C46 C -0.2153(3) 0.1072(4) -0.0010(3) 0.104(3) Uiso 0.70 1 d PD C 5 H46A H -0.1927 0.0775 0.0227 0.157 Uiso 0.70 1 calc PR C 5 H46B H -0.2496 0.0838 -0.0180 0.157 Uiso 0.70 1 calc PR C 5 H46C H -0.2270 0.1462 0.0149 0.157 Uiso 0.70 1 calc PR C 5 C47 C -0.2153(4) 0.1763(4) -0.0750(3) 0.106(3) Uiso 0.70 1 d PD C 5 H47A H -0.2257 0.2162 -0.0593 0.160 Uiso 0.70 1 calc PR C 5 H47B H -0.2504 0.1530 -0.0906 0.160 Uiso 0.70 1 calc PR C 5 H47C H -0.1931 0.1889 -0.0989 0.160 Uiso 0.70 1 calc PR C 5 C45' C -0.1761(9) 0.0621(6) -0.0099(6) 0.118(7) Uiso 0.30 1 d PD C 6 H45D H -0.1479 0.0326 -0.0196 0.177 Uiso 0.30 1 calc PR C 6 H45E H -0.2143 0.0413 -0.0173 0.177 Uiso 0.30 1 calc PR C 6 H45F H -0.1651 0.0703 0.0244 0.177 Uiso 0.30 1 calc PR C 6 C46' C -0.2387(6) 0.1616(12) -0.0398(7) 0.153(10) Uiso 0.30 1 d PD C 6 H46D H -0.2486 0.1891 -0.0684 0.229 Uiso 0.30 1 calc PR C 6 H46E H -0.2378 0.1892 -0.0116 0.229 Uiso 0.30 1 calc PR C 6 H46F H -0.2675 0.1266 -0.0410 0.229 Uiso 0.30 1 calc PR C 6 C47' C -0.1711(9) 0.1143(10) -0.0892(3) 0.111(7) Uiso 0.30 1 d PD C 6 H47D H -0.1546 0.1530 -0.1021 0.167 Uiso 0.30 1 calc PR C 6 H47E H -0.2089 0.1043 -0.1091 0.167 Uiso 0.30 1 calc PR C 6 H47F H -0.1455 0.0761 -0.0890 0.167 Uiso 0.30 1 calc PR C 6 C48 C 0.0445(2) 0.1576(2) 0.0130(2) 0.0768(15) Uani 1 1 d . . . C49 C 0.0788(3) 0.1457(3) 0.0654(3) 0.121(3) Uani 1 1 d . . . H49A H 0.1184 0.1325 0.0649 0.182 Uiso 1 1 calc R . . H49B H 0.0601 0.1106 0.0802 0.182 Uiso 1 1 calc R . . H49C H 0.0793 0.1868 0.0838 0.182 Uiso 1 1 calc R . . C50 C 0.0755(2) 0.2111(3) -0.0114(2) 0.101(2) Uani 1 1 d . . . H50A H 0.0559 0.2157 -0.0448 0.152 Uiso 1 1 calc R . . H50B H 0.1155 0.1978 -0.0098 0.152 Uiso 1 1 calc R . . H50C H 0.0746 0.2537 0.0049 0.152 Uiso 1 1 calc R . . C51 C 0.0443(3) 0.0918(3) -0.0174(3) 0.127(3) Uani 1 1 d . . . H51A H 0.0254 0.1005 -0.0505 0.191 Uiso 1 1 calc R . . H51B H 0.0234 0.0569 -0.0043 0.191 Uiso 1 1 calc R . . H51C H 0.0841 0.0774 -0.0161 0.191 Uiso 1 1 calc R . . O2W O -0.0515(5) 0.4782(5) -0.1704(4) 0.310(6) Uani 1 1 d . . . O1W O 0.0000 0.3829(10) 0.2500 0.358(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 Cu1 0.0460(3) 0.0538(3) 0.0614(4) 0.0086(3) 0.0122(2) -0.0011(2) Cu2 0.0696(4) 0.0592(4) 0.0607(4) 0.0086(3) 0.0142(3) -0.0107(3) O1 0.0450(15) 0.077(2) 0.0472(17) 0.0035(15) 0.0119(13) -0.0046(14) O2 0.080(2) 0.067(2) 0.080(2) 0.0235(19) -0.0044(19) -0.0051(18) O3 0.0396(15) 0.0519(17) 0.0608(18) -0.0021(14) 0.0120(13) -0.0022(13) O4 0.0585(19) 0.0539(18) 0.0594(19) 0.0040(14) 0.0149(15) -0.0101(14) N1 0.044(2) 0.086(3) 0.058(2) 0.021(2) -0.0024(19) -0.0032(19) N2 0.054(2) 0.051(2) 0.077(3) 0.004(2) 0.0184(19) 0.0070(17) N3 0.061(2) 0.060(2) 0.084(3) -0.003(2) 0.035(2) -0.0061(19) N4 0.078(3) 0.067(3) 0.067(3) 0.010(2) 0.018(2) -0.016(2) C1 0.074(3) 0.074(3) 0.054(3) 0.005(3) 0.014(3) 0.001(3) C2 0.080(3) 0.085(4) 0.042(3) 0.002(3) 0.011(2) -0.002(3) C3 0.081(3) 0.101(5) 0.052(3) 0.004(3) 0.009(3) 0.023(3) C4 0.110(5) 0.076(4) 0.060(3) 0.014(3) 0.030(3) 0.035(4) C5 0.112(5) 0.065(3) 0.075(4) 0.011(3) 0.031(3) 0.014(3) C6 0.095(4) 0.066(3) 0.059(3) 0.010(3) 0.026(3) 0.010(3) C7 0.081(3) 0.087(4) 0.053(3) 0.000(3) 0.006(3) -0.007(3) C8 0.128(6) 0.172(7) 0.097(5) 0.031(5) -0.022(4) -0.052(5) C9 0.108(5) 0.120(5) 0.065(4) 0.005(3) 0.020(3) -0.023(4) C10 0.151(6) 0.088(4) 0.115(5) -0.026(4) 0.049(5) -0.028(4) C11 0.099(4) 0.104(5) 0.080(4) 0.013(3) 0.017(3) 0.032(4) C15 0.099(4) 0.072(4) 0.068(4) 0.005(3) 0.030(3) -0.011(3) C16 0.087(4) 0.082(4) 0.091(4) 0.023(3) 0.022(3) -0.025(3) C17 0.068(3) 0.094(4) 0.090(4) 0.001(3) 0.038(3) -0.018(3) C18 0.073(3) 0.077(4) 0.109(5) -0.025(3) 0.041(3) 0.002(3) C19 0.064(3) 0.051(3) 0.131(5) 0.002(3) 0.036(3) 0.009(2) C20 0.045(3) 0.078(4) 0.124(5) 0.015(4) 0.014(3) 0.005(2) C21 0.048(3) 0.112(5) 0.082(4) 0.027(3) -0.001(3) -0.006(3) C22 0.062(3) 0.083(4) 0.054(3) 0.016(3) 0.004(2) -0.006(2) C23 0.055(2) 0.052(3) 0.045(3) 0.008(2) 0.004(2) -0.003(2) C24 0.055(2) 0.041(2) 0.056(3) 0.006(2) 0.013(2) 0.0003(19) C25 0.054(2) 0.049(3) 0.056(3) 0.004(2) 0.014(2) -0.0026(19) C26 0.058(3) 0.064(3) 0.070(3) 0.008(3) 0.020(2) 0.008(2) C27 0.084(4) 0.057(3) 0.060(3) 0.004(2) 0.025(3) 0.004(3) C28 0.069(3) 0.066(3) 0.052(3) 0.004(2) 0.001(2) -0.007(2) C29 0.044(2) 0.091(4) 0.055(3) -0.002(3) 0.005(2) 0.004(2) C30 0.099(4) 0.071(4) 0.069(3) 0.011(3) 0.000(3) 0.017(3) C31 0.069(3) 0.078(4) 0.073(3) -0.009(3) 0.001(3) -0.013(3) C32 0.051(3) 0.201(8) 0.083(4) -0.002(4) 0.012(3) 0.013(4) C33 0.092(4) 0.092(4) 0.062(3) -0.005(3) 0.025(3) 0.004(3) C37 0.038(2) 0.055(3) 0.077(3) -0.002(2) 0.021(2) 0.0009(19) C38 0.041(2) 0.055(3) 0.062(3) 0.009(2) 0.015(2) 0.0025(19) C39 0.038(2) 0.046(2) 0.067(3) 0.011(2) 0.011(2) 0.0000(19) C40 0.043(2) 0.049(3) 0.081(3) 0.004(2) 0.010(2) 0.000(2) C41 0.056(3) 0.056(3) 0.101(4) -0.012(3) 0.018(3) 0.001(2) C42 0.044(2) 0.067(3) 0.078(3) 0.005(3) 0.010(2) -0.005(2) C43 0.039(2) 0.057(3) 0.078(3) 0.003(2) 0.015(2) 0.003(2) C44 0.059(3) 0.083(4) 0.104(4) -0.015(3) 0.012(3) -0.011(3) C48 0.049(3) 0.051(3) 0.133(5) -0.012(3) 0.024(3) 0.008(2) C49 0.070(4) 0.091(5) 0.194(8) 0.031(5) 0.003(4) 0.028(3) C50 0.067(3) 0.090(4) 0.163(6) -0.024(4) 0.061(4) -0.004(3) C51 0.074(4) 0.085(4) 0.228(9) -0.059(5) 0.043(5) 0.005(3) O2W 0.337(12) 0.196(8) 0.371(14) 0.037(8) 0.010(10) 0.121(8) O1W 0.310(19) 0.53(3) 0.203(13) 0.000 -0.014(12) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.909(3) . ? Cu1 N1 1.924(4) . ? Cu1 O4 1.958(3) . ? Cu1 N2 2.131(3) . ? Cu1 O3 2.196(3) . ? Cu1 Cu2 3.0150(8) . ? Cu2 O2 1.906(3) . ? Cu2 N4 1.933(4) . ? Cu2 O4 1.942(3) . ? Cu2 O3 2.094(3) . ? Cu2 N3 2.291(4) . ? O1 C24 1.320(5) . ? O2 C1 1.302(5) . ? O3 C39 1.319(4) . ? O4 H4 0.961(19) . ? N1 C22 1.280(6) . ? N1 C21 1.479(6) . ? N2 C20 1.482(6) . ? N2 C37 1.486(5) . ? N2 C19 1.513(6) . ? N3 C37 1.472(6) . ? N3 C18 1.479(6) . ? N3 C17 1.490(6) . ? N4 C15 1.269(6) . ? N4 C16 1.467(6) . ? C1 C2 1.409(6) . ? C1 C6 1.445(7) . ? C2 C3 1.385(7) . ? C2 C7 1.522(7) . ? C3 C4 1.406(8) . ? C3 H3 0.9300 . ? C4 C5 1.330(7) . ? C4 C11 1.573(7) . ? C5 C6 1.410(7) . ? C5 H5 0.9300 . ? C6 C15 1.425(7) . ? C7 C8 1.529(8) . ? C7 C9 1.529(7) . ? C7 C10 1.533(8) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C13 1.488(5) . ? C11 C12' 1.488(5) . ? C11 C14' 1.488(5) . ? C11 C12 1.488(5) . ? C11 C13' 1.488(5) . ? C11 C14 1.489(5) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C12' H12D 0.9600 . ? C12' H12E 0.9600 . ? C12' H12F 0.9600 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? C14' H14D 0.9600 . ? C14' H14E 0.9600 . ? C14' H14F 0.9600 . ? C15 H15 0.9300 . ? C16 C17 1.495(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.493(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.504(8) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.419(6) . ? C22 H22 0.9300 . ? C23 C28 1.388(6) . ? C23 C24 1.402(6) . ? C24 C25 1.427(6) . ? C25 C26 1.386(6) . ? C25 C29 1.536(6) . ? C26 C27 1.393(7) . ? C26 H26 0.9300 . ? C27 C28 1.361(6) . ? C27 C33 1.548(7) . ? C28 H28 0.9300 . ? C29 C31 1.511(7) . ? C29 C32 1.523(6) . ? C29 C30 1.540(7) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 C34 1.523(5) . ? C33 C36' 1.523(5) . ? C33 C34' 1.523(5) . ? C33 C35 1.523(5) . ? C33 C35' 1.523(5) . ? C33 C36 1.524(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C34' H34D 0.9600 . ? C34' H34E 0.9600 . ? C34' H34F 0.9600 . ? C35' H35D 0.9600 . ? C35' H35E 0.9600 . ? C35' H35F 0.9600 . ? C36' H36D 0.9600 . ? C36' H36E 0.9600 . ? C36' H36F 0.9600 . ? C37 C38 1.487(6) . ? C37 H37 0.9800 . ? C38 C43 1.402(6) . ? C38 C39 1.413(5) . ? C39 C40 1.415(6) . ? C40 C41 1.391(6) . ? C40 C48 1.528(6) . ? C41 C42 1.403(6) . ? C41 H41 0.9300 . ? C42 C43 1.355(6) . ? C42 C44 1.527(6) . ? C43 H43 0.9300 . ? C44 C45 1.535(5) . ? C44 C46' 1.535(5) . ? C44 C46 1.535(5) . ? C44 C47' 1.535(5) . ? C44 C45' 1.536(5) . ? C44 C47 1.536(5) . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? C47 H47A 0.9600 . ? C47 H47B 0.9600 . ? C47 H47C 0.9600 . ? C45' H45D 0.9600 . ? C45' H45E 0.9600 . ? C45' H45F 0.9600 . ? C46' H46D 0.9600 . ? C46' H46E 0.9600 . ? C46' H46F 0.9600 . ? C47' H47D 0.9600 . ? C47' H47E 0.9600 . ? C47' H47F 0.9600 . ? C48 C50 1.522(7) . ? C48 C49 1.544(8) . ? C48 C51 1.555(7) . ? C49 H49A 0.9600 . ? C49 H49B 0.9600 . ? C49 H49C 0.9600 . ? C50 H50A 0.9600 . ? C50 H50B 0.9600 . ? C50 H50C 0.9600 . ? C51 H51A 0.9600 . ? C51 H51B 0.9600 . ? C51 H51C 0.9600 . ? 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 91.88(14) . . ? O1 Cu1 O4 90.19(12) . . ? N1 Cu1 O4 171.82(15) . . ? O1 Cu1 N2 168.55(13) . . ? N1 Cu1 N2 84.14(15) . . ? O4 Cu1 N2 92.31(14) . . ? O1 Cu1 O3 102.13(11) . . ? N1 Cu1 O3 105.79(14) . . ? O4 Cu1 O3 81.48(11) . . ? N2 Cu1 O3 89.29(11) . . ? O1 Cu1 Cu2 106.68(9) . . ? N1 Cu1 Cu2 146.59(11) . . ? O4 Cu1 Cu2 39.17(8) . . ? N2 Cu1 Cu2 82.05(11) . . ? O3 Cu1 Cu2 43.99(7) . . ? O2 Cu2 N4 91.05(16) . . ? O2 Cu2 O4 91.04(13) . . ? N4 Cu2 O4 171.95(16) . . ? O2 Cu2 O3 130.70(14) . . ? N4 Cu2 O3 99.92(14) . . ? O4 Cu2 O3 84.55(12) . . ? O2 Cu2 N3 144.66(16) . . ? N4 Cu2 N3 81.55(16) . . ? O4 Cu2 N3 92.28(13) . . ? O3 Cu2 N3 84.64(12) . . ? O2 Cu2 Cu1 122.80(10) . . ? N4 Cu2 Cu1 142.40(12) . . ? O4 Cu2 Cu1 39.57(9) . . ? O3 Cu2 Cu1 46.74(8) . . ? N3 Cu2 Cu1 78.76(10) . . ? C24 O1 Cu1 128.7(3) . . ? C1 O2 Cu2 130.0(3) . . ? C39 O3 Cu2 125.7(2) . . ? C39 O3 Cu1 113.7(2) . . ? Cu2 O3 Cu1 89.28(10) . . ? Cu2 O4 Cu1 101.26(13) . . ? Cu2 O4 H4 112(3) . . ? Cu1 O4 H4 96(3) . . ? C22 N1 C21 118.9(4) . . ? C22 N1 Cu1 125.8(3) . . ? C21 N1 Cu1 115.3(3) . . ? C20 N2 C37 113.7(4) . . ? C20 N2 C19 111.0(4) . . ? C37 N2 C19 102.4(3) . . ? C20 N2 Cu1 103.9(3) . . ? C37 N2 Cu1 113.4(2) . . ? C19 N2 Cu1 112.7(3) . . ? C37 N3 C18 102.7(4) . . ? C37 N3 C17 113.7(4) . . ? C18 N3 C17 112.8(4) . . ? C37 N3 Cu2 114.0(2) . . ? C18 N3 Cu2 111.2(3) . . ? C17 N3 Cu2 102.8(3) . . ? C15 N4 C16 119.6(4) . . ? C15 N4 Cu2 125.8(4) . . ? C16 N4 Cu2 114.5(3) . . ? O2 C1 C2 121.9(5) . . ? O2 C1 C6 120.6(5) . . ? C2 C1 C6 117.5(5) . . ? C3 C2 C1 118.6(5) . . ? C3 C2 C7 121.1(5) . . ? C1 C2 C7 120.3(5) . . ? C2 C3 C4 124.3(5) . . ? C2 C3 H3 117.9 . . ? C4 C3 H3 117.9 . . ? C5 C4 C3 117.0(5) . . ? C5 C4 C11 123.2(6) . . ? C3 C4 C11 119.8(6) . . ? C4 C5 C6 123.1(6) . . ? C4 C5 H5 118.4 . . ? C6 C5 H5 118.4 . . ? C5 C6 C15 118.0(5) . . ? C5 C6 C1 119.5(5) . . ? C15 C6 C1 122.2(5) . . ? C2 C7 C8 112.5(5) . . ? C2 C7 C9 109.9(4) . . ? C8 C7 C9 105.6(5) . . ? C2 C7 C10 109.8(5) . . ? C8 C7 C10 108.5(5) . . ? C9 C7 C10 110.5(5) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C11 C12' 135.4(11) . . ? C13 C11 C14' 70.7(8) . . ? C12' C11 C14' 106.8(7) . . ? C13 C11 C12 108.8(3) . . ? C12' C11 C12 41.8(7) . . ? C14' C11 C12 136.4(12) . . ? C13 C11 C13' 40.6(7) . . ? C12' C11 C13' 106.8(7) . . ? C14' C11 C13' 106.8(7) . . ? C12 C11 C13' 70.0(7) . . ? C13 C11 C14 108.8(3) . . ? C12' C11 C14 69.3(8) . . ? C14' C11 C14 40.9(7) . . ? C12 C11 C14 108.7(3) . . ? C13' C11 C14 133.4(12) . . ? C13 C11 C4 110.8(5) . . ? C12' C11 C4 110.9(11) . . ? C14' C11 C4 112.1(11) . . ? C12 C11 C4 108.5(6) . . ? C13' C11 C4 113.0(12) . . ? C14 C11 C4 111.2(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C11 C12' H12D 109.5 . . ? C11 C12' H12E 109.5 . . ? H12D C12' H12E 109.5 . . ? C11 C12' H12F 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? C11 C13' H13D 109.5 . . ? C11 C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C11 C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C11 C14' H14D 109.5 . . ? C11 C14' H14E 109.5 . . ? H14D C14' H14E 109.5 . . ? C11 C14' H14F 109.5 . . ? H14D C14' H14F 109.5 . . ? H14E C14' H14F 109.5 . . ? N4 C15 C6 126.7(5) . . ? N4 C15 H15 116.6 . . ? C6 C15 H15 116.6 . . ? N4 C16 C17 108.1(4) . . ? N4 C16 H16A 110.1 . . ? C17 C16 H16A 110.1 . . ? N4 C16 H16B 110.1 . . ? C17 C16 H16B 110.1 . . ? H16A C16 H16B 108.4 . . ? N3 C17 C16 110.8(4) . . ? N3 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? N3 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? N3 C18 C19 104.6(4) . . ? N3 C18 H18A 110.8 . . ? C19 C18 H18A 110.8 . . ? N3 C18 H18B 110.8 . . ? C19 C18 H18B 110.8 . . ? H18A C18 H18B 108.9 . . ? C18 C19 N2 105.7(4) . . ? C18 C19 H19A 110.6 . . ? N2 C19 H19A 110.6 . . ? C18 C19 H19B 110.6 . . ? N2 C19 H19B 110.6 . . ? H19A C19 H19B 108.7 . . ? N2 C20 C21 112.0(4) . . ? N2 C20 H20A 109.2 . . ? C21 C20 H20A 109.2 . . ? N2 C20 H20B 109.2 . . ? C21 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? N1 C21 C20 106.8(4) . . ? N1 C21 H21A 110.4 . . ? C20 C21 H21A 110.4 . . ? N1 C21 H21B 110.4 . . ? C20 C21 H21B 110.4 . . ? H21A C21 H21B 108.6 . . ? N1 C22 C23 127.7(4) . . ? N1 C22 H22 116.2 . . ? C23 C22 H22 116.2 . . ? C28 C23 C24 120.7(4) . . ? C28 C23 C22 117.3(4) . . ? C24 C23 C22 122.0(4) . . ? O1 C24 C23 122.9(4) . . ? O1 C24 C25 119.1(4) . . ? C23 C24 C25 118.0(4) . . ? C26 C25 C24 117.4(4) . . ? C26 C25 C29 121.8(4) . . ? C24 C25 C29 120.7(4) . . ? C25 C26 C27 125.1(4) . . ? C25 C26 H26 117.4 . . ? C27 C26 H26 117.4 . . ? C28 C27 C26 115.6(4) . . ? C28 C27 C33 124.2(5) . . ? C26 C27 C33 120.1(4) . . ? C27 C28 C23 123.1(4) . . ? C27 C28 H28 118.4 . . ? C23 C28 H28 118.4 . . ? C31 C29 C32 107.9(4) . . ? C31 C29 C25 111.0(4) . . ? C32 C29 C25 111.2(4) . . ? C31 C29 C30 111.5(4) . . ? C32 C29 C30 107.1(4) . . ? C25 C29 C30 107.9(4) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C34 C33 C36' 133.9(8) . . ? C34 C33 C34' 50.8(5) . . ? C36' C33 C34' 108.0(5) . . ? C34 C33 C35 108.6(3) . . ? C36' C33 C35 54.0(5) . . ? C34' C33 C35 135.6(9) . . ? C34 C33 C35' 59.0(5) . . ? C36' C33 C35' 108.0(5) . . ? C34' C33 C35' 107.9(5) . . ? C35 C33 C35' 56.4(5) . . ? C34 C33 C36 108.6(3) . . ? C36' C33 C36 55.9(5) . . ? C34' C33 C36 59.8(5) . . ? C35 C33 C36 108.5(3) . . ? C35' C33 C36 146.7(9) . . ? C34 C33 C27 111.2(6) . . ? C36' C33 C27 114.9(7) . . ? C34' C33 C27 112.9(8) . . ? C35 C33 C27 111.3(6) . . ? C35' C33 C27 104.7(8) . . ? C36 C33 C27 108.5(5) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C33 C34' H34D 109.5 . . ? C33 C34' H34E 109.5 . . ? H34D C34' H34E 109.5 . . ? C33 C34' H34F 109.5 . . ? H34D C34' H34F 109.5 . . ? H34E C34' H34F 109.5 . . ? C33 C35' H35D 109.5 . . ? C33 C35' H35E 109.5 . . ? H35D C35' H35E 109.5 . . ? C33 C35' H35F 109.5 . . ? H35D C35' H35F 109.5 . . ? H35E C35' H35F 109.5 . . ? C33 C36' H36D 109.5 . . ? C33 C36' H36E 109.5 . . ? H36D C36' H36E 109.5 . . ? C33 C36' H36F 109.5 . . ? H36D C36' H36F 109.5 . . ? H36E C36' H36F 109.5 . . ? N3 C37 N2 101.0(3) . . ? N3 C37 C38 115.9(4) . . ? N2 C37 C38 116.8(3) . . ? N3 C37 H37 107.5 . . ? N2 C37 H37 107.5 . . ? C38 C37 H37 107.5 . . ? C43 C38 C39 120.5(4) . . ? C43 C38 C37 118.9(4) . . ? C39 C38 C37 120.6(4) . . ? O3 C39 C38 119.3(4) . . ? O3 C39 C40 122.5(3) . . ? C38 C39 C40 118.2(4) . . ? C41 C40 C39 118.2(4) . . ? C41 C40 C48 121.5(4) . . ? C39 C40 C48 120.3(4) . . ? C40 C41 C42 124.0(4) . . ? C40 C41 H41 118.0 . . ? C42 C41 H41 118.0 . . ? C43 C42 C41 116.8(4) . . ? C43 C42 C44 121.1(4) . . ? C41 C42 C44 122.1(4) . . ? C42 C43 C38 122.4(4) . . ? C42 C43 H43 118.8 . . ? C38 C43 H43 118.8 . . ? C42 C44 C45 113.1(5) . . ? C42 C44 C46' 117.0(11) . . ? C45 C44 C46' 129.3(11) . . ? C42 C44 C46 109.6(5) . . ? C45 C44 C46 108.6(3) . . ? C46' C44 C46 60.6(6) . . ? C42 C44 C47' 109.6(9) . . ? C45 C44 C47' 45.4(6) . . ? C46' C44 C47' 108.2(6) . . ? C46 C44 C47' 139.7(9) . . ? C42 C44 C45' 105.4(8) . . ? C45 C44 C45' 63.5(6) . . ? C46' C44 C45' 108.2(6) . . ? C46 C44 C45' 51.5(6) . . ? C47' C44 C45' 108.1(6) . . ? C42 C44 C47 108.3(5) . . ? C45 C44 C47 108.6(3) . . ? C46' C44 C47 48.5(6) . . ? C46 C44 C47 108.5(3) . . ? C47' C44 C47 67.2(6) . . ? C45' C44 C47 145.4(9) . . ? C44 C45 H45A 109.5 . . ? C44 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C44 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C44 C46 H46A 109.5 . . ? C44 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C44 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C44 C47 H47A 109.5 . . ? C44 C47 H47B 109.5 . . ? H47A C47 H47B 109.5 . . ? C44 C47 H47C 109.5 . . ? H47A C47 H47C 109.5 . . ? H47B C47 H47C 109.5 . . ? C44 C45' H45D 109.5 . . ? C44 C45' H45E 109.5 . . ? H45D C45' H45E 109.5 . . ? C44 C45' H45F 109.5 . . ? H45D C45' H45F 109.5 . . ? H45E C45' H45F 109.5 . . ? C44 C46' H46D 109.5 . . ? C44 C46' H46E 109.5 . . ? H46D C46' H46E 109.5 . . ? C44 C46' H46F 109.5 . . ? H46D C46' H46F 109.5 . . ? H46E C46' H46F 109.5 . . ? C44 C47' H47D 109.5 . . ? C44 C47' H47E 109.5 . . ? H47D C47' H47E 109.5 . . ? C44 C47' H47F 109.5 . . ? H47D C47' H47F 109.5 . . ? H47E C47' H47F 109.5 . . ? C50 C48 C40 109.3(4) . . ? C50 C48 C49 109.8(5) . . ? C40 C48 C49 108.7(5) . . ? C50 C48 C51 106.2(5) . . ? C40 C48 C51 112.8(4) . . ? C49 C48 C51 110.0(5) . . ? C48 C49 H49A 109.5 . . ? C48 C49 H49B 109.5 . . ? H49A C49 H49B 109.5 . . ? C48 C49 H49C 109.5 . . ? H49A C49 H49C 109.5 . . ? H49B C49 H49C 109.5 . . ? C48 C50 H50A 109.5 . . ? C48 C50 H50B 109.5 . . ? H50A C50 H50B 109.5 . . ? C48 C50 H50C 109.5 . . ? H50A C50 H50C 109.5 . . ? H50B C50 H50C 109.5 . . ? C48 C51 H51A 109.5 . . ? C48 C51 H51B 109.5 . . ? H51A C51 H51B 109.5 . . ? C48 C51 H51C 109.5 . . ? H51A C51 H51C 109.5 . . ? H51B C51 H51C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.628 _refine_diff_density_min -0.367 _refine_diff_density_rms 0.067 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 1.000 -0.132 0.250 690 185 ' ' 2 1.000 0.132 0.750 690 183 ' ' 3 0.500 0.368 0.250 690 185 ' ' 4 0.500 0.632 0.750 690 183 ' ' _platon_squeeze_details ; PLATON (A.L. Spek, Acta Cryst. 2009, D65, 148-155) ; _database_code_depnum_ccdc_archive 'CCDC 840821'