# Electronic Supplementary Material (ESI) for CrystEngComm # 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_cmd175c1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu5(L1)4(MeOH)4](ClO4)2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H56 Cl2 Cu5 N8 O20' _chemical_formula_weight 1357.53 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 C2/c _space_group_name_Hall '-C 2yc' 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 17.9896(7) _cell_length_b 12.2939(4) _cell_length_c 23.8922(9) _cell_angle_alpha 90.00 _cell_angle_beta 107.805(4) _cell_angle_gamma 90.00 _cell_volume 5031.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3722 _cell_measurement_theta_min 2.9385 _cell_measurement_theta_max 25.35 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.792 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2764 _exptl_absorpt_coefficient_mu 2.271 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78766 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 10897 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 -0.0371406000 _diffrn_orient_matrix_UB_12 0.0140649000 _diffrn_orient_matrix_UB_21 -0.0143199000 _diffrn_orient_matrix_UB_22 0.0073598000 _diffrn_orient_matrix_UB_23 0.0242858000 _diffrn_orient_matrix_UB_31 0.0113692000 _diffrn_orient_matrix_UB_32 0.0555147000 _diffrn_orient_matrix_UB_33 0.0017401000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 18.00 56.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -14.2653 77.0000 90.0000 38 #__ type_ start__ end____ width___ exp.time_ 2 omega 36.00 70.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 77.0000 -180.0000 34 #__ type_ start__ end____ width___ exp.time_ 3 omega 22.00 78.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 77.0000 -120.0000 56 #__ type_ start__ end____ width___ exp.time_ 4 omega -7.00 71.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 77.0000 0.0000 78 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150.0 _reflns_number_total 4607 _reflns_number_gt 3637 _reflns_threshold_expression >2sigma(I) _computing_structure_solution SHELXS97 _computing_structure_refinement 'SHELXL-97/2 (Sheldrick,1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0327P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4607 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0611 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.0910 _refine_ls_wR_factor_gt 0.0842 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.7500 0.7500 0.0000 0.01355(17) Uani 1 2 d S . . Cu2 Cu 0.92089(3) 0.81153(4) 0.08643(2) 0.01696(14) Uani 1 1 d . . . Cu3 Cu 0.78371(3) 0.49272(4) 0.035042(19) 0.01334(13) Uani 1 1 d . . . Cl1 Cl 0.77019(6) 1.07722(9) 0.20020(4) 0.0221(2) Uani 1 1 d . . . N1 N 0.85558(17) 0.9253(3) 0.04321(13) 0.0145(7) Uani 1 1 d . . . N2 N 1.00291(18) 0.9241(3) 0.12758(14) 0.0210(8) Uani 1 1 d . . . N3 N 0.86604(17) 0.5987(2) 0.06355(13) 0.0133(7) Uani 1 1 d . . . N4 N 0.83274(17) 0.3888(3) 0.10245(13) 0.0138(7) Uani 1 1 d . . . O1 O 0.81811(14) 1.0789(2) -0.01001(11) 0.0175(6) Uani 1 1 d . . . O2 O 0.77612(14) 0.8977(2) 0.01792(11) 0.0182(6) Uani 1 1 d . . . O3 O 0.97023(14) 0.6837(2) 0.12619(11) 0.0191(6) Uani 1 1 d . . . O4 O 0.85355(14) 0.7029(2) 0.03796(11) 0.0159(6) Uani 1 1 d . . . O5 O 0.82974(15) 0.4123(2) -0.03491(11) 0.0219(7) Uani 1 1 d . . . H5 H 0.7987 0.3615 -0.0621 0.026 Uiso 1 1 calc R . . O6 O 0.84616(17) 1.1242(3) 0.21845(13) 0.0447(9) Uani 1 1 d . . . O7 O 0.71181(19) 1.1592(3) 0.18701(14) 0.0428(9) Uani 1 1 d . . . O8 O 0.76169(18) 1.0070(3) 0.24528(13) 0.0400(9) Uani 1 1 d . . . O9 O 0.76202(18) 1.0141(3) 0.14740(12) 0.0372(9) Uani 1 1 d . . . O10 O 0.8182(2) 0.7997(3) 0.14028(16) 0.0615(12) Uani 1 1 d . . . H10 H 0.7724 0.8409 0.1224 0.074 Uiso 1 1 calc R . . C1 C 1.0781(3) 0.8647(4) 0.1554(2) 0.0514(16) Uani 1 1 d . . . H1A H 1.1040 0.8497 0.1256 0.077 Uiso 1 1 calc R . . H1B H 1.0672 0.7960 0.1721 0.077 Uiso 1 1 calc R . . H1C H 1.1123 0.9097 0.1867 0.077 Uiso 1 1 calc R . . C2 C 0.9740(3) 0.9672(4) 0.17499(19) 0.0413(14) Uani 1 1 d . . . H2A H 1.0130 1.0166 0.2000 0.062 Uiso 1 1 calc R . . H2B H 0.9647 0.9068 0.1988 0.062 Uiso 1 1 calc R . . H2C H 0.9251 1.0069 0.1576 0.062 Uiso 1 1 calc R . . C3 C 1.0140(2) 1.0185(3) 0.09296(16) 0.0152(9) Uani 1 1 d . . . C4 C 1.0864(2) 1.0694(4) 0.10806(18) 0.0217(10) Uani 1 1 d . . . H4 H 1.1287 1.0391 0.1383 0.026 Uiso 1 1 calc R . . C5 C 1.0984(2) 1.1631(4) 0.08000(18) 0.0239(10) Uani 1 1 d . . . H5A H 1.1487 1.1956 0.0906 0.029 Uiso 1 1 calc R . . C6 C 1.0375(2) 1.2095(4) 0.03665(18) 0.0230(10) Uani 1 1 d . . . H6 H 1.0452 1.2750 0.0181 0.028 Uiso 1 1 calc R . . C7 C 0.9654(2) 1.1594(3) 0.02063(17) 0.0187(9) Uani 1 1 d . . . H7 H 0.9237 1.1905 -0.0098 0.022 Uiso 1 1 calc R . . C8 C 0.9519(2) 1.0634(3) 0.04823(16) 0.0135(8) Uani 1 1 d . . . C9 C 0.8709(2) 1.0202(3) 0.02642(16) 0.0163(9) Uani 1 1 d . . . C10 C 0.8067(2) 0.2782(3) 0.07965(17) 0.0222(10) Uani 1 1 d . . . H10A H 0.8370 0.2539 0.0541 0.033 Uiso 1 1 calc R . . H10B H 0.7512 0.2801 0.0571 0.033 Uiso 1 1 calc R . . H10C H 0.8148 0.2276 0.1127 0.033 Uiso 1 1 calc R . . C11 C 0.7941(2) 0.4169(4) 0.14779(17) 0.0241(10) Uani 1 1 d . . . H11A H 0.8076 0.3623 0.1792 0.036 Uiso 1 1 calc R . . H11B H 0.7373 0.4183 0.1295 0.036 Uiso 1 1 calc R . . H11C H 0.8120 0.4887 0.1644 0.036 Uiso 1 1 calc R . . C12 C 0.9184(2) 0.3926(3) 0.13124(16) 0.0154(9) Uani 1 1 d . . . C13 C 0.9571(2) 0.3007(3) 0.15738(16) 0.0199(9) Uani 1 1 d . . . H13 H 0.9288 0.2347 0.1547 0.024 Uiso 1 1 calc R . . C14 C 1.0361(2) 0.3012(4) 0.18742(17) 0.0222(10) Uani 1 1 d . . . H14 H 1.0614 0.2361 0.2046 0.027 Uiso 1 1 calc R . . C15 C 1.0778(2) 0.3964(4) 0.19229(17) 0.0229(10) Uani 1 1 d . . . H15 H 1.1322 0.3976 0.2127 0.027 Uiso 1 1 calc R . . C16 C 1.0398(2) 0.4900(4) 0.16723(17) 0.0208(10) Uani 1 1 d . . . H16 H 1.0687 0.5558 0.1716 0.025 Uiso 1 1 calc R . . C17 C 0.9602(2) 0.4916(3) 0.13550(16) 0.0145(9) Uani 1 1 d . . . C18 C 0.9304(2) 0.5966(3) 0.10797(16) 0.0149(9) Uani 1 1 d . . . C19 C 0.9057(2) 0.4405(4) -0.03645(19) 0.0308(11) Uani 1 1 d . . . H19A H 0.9055 0.5157 -0.0501 0.046 Uiso 1 1 calc R . . H19B H 0.9210 0.3916 -0.0634 0.046 Uiso 1 1 calc R . . H19C H 0.9429 0.4337 0.0031 0.046 Uiso 1 1 calc R . . C20 C 0.8163(3) 0.7439(4) 0.1914(2) 0.0496(15) Uani 1 1 d . . . H20A H 0.8651 0.7034 0.2075 0.074 Uiso 1 1 calc R . . H20B H 0.7722 0.6932 0.1815 0.074 Uiso 1 1 calc R . . H20C H 0.8104 0.7964 0.2206 0.074 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 0.0112(3) 0.0096(4) 0.0173(3) 0.0022(3) 0.0005(3) -0.0019(3) Cu2 0.0129(3) 0.0114(3) 0.0217(3) 0.0014(2) -0.0019(2) -0.0018(2) Cu3 0.0117(3) 0.0106(3) 0.0161(2) 0.0017(2) 0.00168(19) -0.0013(2) Cl1 0.0218(5) 0.0243(6) 0.0198(5) -0.0020(5) 0.0057(4) -0.0041(5) N1 0.0083(16) 0.0138(18) 0.0187(17) -0.0009(15) -0.0001(13) -0.0040(15) N2 0.0170(18) 0.017(2) 0.0213(18) 0.0020(16) -0.0060(14) -0.0022(16) N3 0.0144(17) 0.0082(17) 0.0157(16) 0.0065(14) 0.0022(13) 0.0008(15) N4 0.0120(17) 0.0116(18) 0.0165(16) 0.0007(14) 0.0023(13) -0.0035(15) O1 0.0120(14) 0.0153(16) 0.0215(14) 0.0050(12) -0.0003(11) -0.0014(13) O2 0.0107(14) 0.0156(16) 0.0241(15) 0.0002(13) -0.0011(11) -0.0038(12) O3 0.0137(14) 0.0142(15) 0.0241(15) 0.0004(13) -0.0020(12) -0.0030(13) O4 0.0145(14) 0.0090(14) 0.0207(14) 0.0056(12) 0.0003(11) -0.0031(12) O5 0.0192(15) 0.0243(18) 0.0231(15) -0.0083(13) 0.0078(12) -0.0070(14) O6 0.0292(19) 0.060(3) 0.0389(19) -0.0038(18) 0.0012(15) -0.0255(19) O7 0.041(2) 0.044(2) 0.044(2) -0.0005(18) 0.0149(16) 0.0186(19) O8 0.038(2) 0.052(2) 0.0303(17) 0.0148(17) 0.0104(15) -0.0104(18) O9 0.048(2) 0.033(2) 0.0221(16) -0.0072(15) -0.0027(14) 0.0110(18) O10 0.104(3) 0.044(2) 0.058(2) 0.029(2) 0.057(2) 0.035(2) C1 0.025(3) 0.026(3) 0.075(4) 0.019(3) -0.026(3) -0.008(2) C2 0.066(4) 0.037(3) 0.022(2) -0.006(2) 0.014(2) -0.029(3) C3 0.018(2) 0.012(2) 0.015(2) -0.0048(17) 0.0056(17) -0.0014(18) C4 0.008(2) 0.024(3) 0.029(2) -0.004(2) 0.0008(17) 0.0035(19) C5 0.016(2) 0.028(3) 0.030(2) -0.003(2) 0.0105(19) -0.010(2) C6 0.023(2) 0.023(3) 0.028(2) 0.003(2) 0.0151(19) -0.004(2) C7 0.020(2) 0.018(2) 0.020(2) -0.0004(19) 0.0085(17) -0.0021(19) C8 0.0103(19) 0.014(2) 0.016(2) -0.0036(18) 0.0050(16) 0.0025(18) C9 0.019(2) 0.015(2) 0.0142(19) -0.0007(18) 0.0052(17) 0.0005(19) C10 0.021(2) 0.013(2) 0.025(2) 0.0022(19) -0.0035(18) -0.0023(19) C11 0.020(2) 0.035(3) 0.020(2) 0.000(2) 0.0101(18) 0.000(2) C12 0.012(2) 0.017(2) 0.0152(19) 0.0015(18) 0.0023(16) -0.0006(18) C13 0.022(2) 0.016(2) 0.020(2) 0.0020(19) 0.0048(18) 0.000(2) C14 0.022(2) 0.020(2) 0.023(2) 0.007(2) 0.0044(18) 0.007(2) C15 0.017(2) 0.026(3) 0.022(2) 0.006(2) -0.0005(18) 0.006(2) C16 0.020(2) 0.018(2) 0.021(2) 0.0021(19) 0.0029(17) -0.005(2) C17 0.016(2) 0.014(2) 0.0129(19) -0.0005(17) 0.0036(16) 0.0013(19) C18 0.012(2) 0.015(2) 0.019(2) -0.0028(18) 0.0071(17) -0.0011(18) C19 0.027(3) 0.035(3) 0.035(3) 0.000(2) 0.015(2) -0.004(2) C20 0.081(4) 0.034(3) 0.033(3) 0.005(3) 0.017(3) -0.003(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.892(3) 7_665 ? Cu1 O2 1.892(3) . ? Cu1 O4 1.896(2) 7_665 ? Cu1 O4 1.896(2) . ? Cu2 O3 1.909(3) . ? Cu2 N1 1.913(3) . ? Cu2 O4 1.932(3) . ? Cu2 N2 2.042(3) . ? Cu2 O10 2.558(3) . ? Cu3 N3 1.933(3) . ? Cu3 O2 1.934(3) 7_665 ? Cu3 O1 1.954(2) 7_665 ? Cu3 N4 2.034(3) . ? Cu3 O5 2.303(3) . ? Cl1 O7 1.420(3) . ? Cl1 O6 1.424(3) . ? Cl1 O8 1.425(3) . ? Cl1 O9 1.450(3) . ? N1 C9 1.291(5) . ? N1 O2 1.412(4) . ? N2 C3 1.474(5) . ? N2 C2 1.482(5) . ? N2 C1 1.502(5) . ? N3 C18 1.309(4) . ? N3 O4 1.408(4) . ? N4 C12 1.483(4) . ? N4 C10 1.486(5) . ? N4 C11 1.496(4) . ? O1 C9 1.294(4) . ? O1 Cu3 1.954(2) 7_665 ? O2 Cu3 1.934(3) 7_665 ? O3 C18 1.288(4) . ? O5 C19 1.421(4) . ? O5 H5 0.9500 . ? O10 C20 1.409(5) . ? O10 H10 0.9500 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.390(5) . ? C3 C8 1.401(5) . ? C4 C5 1.382(6) . ? C4 H4 0.9500 . ? C5 C6 1.379(6) . ? C5 H5A 0.9500 . ? C6 C7 1.381(5) . ? C6 H6 0.9500 . ? C7 C8 1.409(5) . ? C7 H7 0.9500 . ? C8 C9 1.487(5) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.373(5) . ? C12 C17 1.419(5) . ? C13 C14 1.381(5) . ? C13 H13 0.9500 . ? C14 C15 1.376(6) . ? C14 H14 0.9500 . ? C15 C16 1.378(6) . ? C15 H15 0.9500 . ? C16 C17 1.401(5) . ? C16 H16 0.9500 . ? C17 C18 1.473(5) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 179.997(1) 7_665 . ? O2 Cu1 O4 92.59(11) 7_665 7_665 ? O2 Cu1 O4 87.41(11) . 7_665 ? O2 Cu1 O4 87.41(11) 7_665 . ? O2 Cu1 O4 92.59(11) . . ? O4 Cu1 O4 180.0 7_665 . ? O3 Cu2 N1 170.28(12) . . ? O3 Cu2 O4 80.81(11) . . ? N1 Cu2 O4 90.72(12) . . ? O3 Cu2 N2 99.25(12) . . ? N1 Cu2 N2 89.92(13) . . ? O4 Cu2 N2 170.04(12) . . ? O3 Cu2 O10 90.02(11) . . ? N1 Cu2 O10 83.93(12) . . ? O4 Cu2 O10 81.10(12) . . ? N2 Cu2 O10 108.85(14) . . ? N3 Cu3 O2 88.54(12) . 7_665 ? N3 Cu3 O1 163.14(12) . 7_665 ? O2 Cu3 O1 80.30(11) 7_665 7_665 ? N3 Cu3 N4 92.53(12) . . ? O2 Cu3 N4 167.29(12) 7_665 . ? O1 Cu3 N4 95.63(11) 7_665 . ? N3 Cu3 O5 97.94(11) . . ? O2 Cu3 O5 94.34(10) 7_665 . ? O1 Cu3 O5 95.50(10) 7_665 . ? N4 Cu3 O5 98.05(11) . . ? O7 Cl1 O6 110.8(2) . . ? O7 Cl1 O8 110.8(2) . . ? O6 Cl1 O8 109.23(18) . . ? O7 Cl1 O9 108.40(18) . . ? O6 Cl1 O9 108.42(19) . . ? O8 Cl1 O9 109.1(2) . . ? C9 N1 O2 111.6(3) . . ? C9 N1 Cu2 132.4(3) . . ? O2 N1 Cu2 115.5(2) . . ? C3 N2 C2 106.6(3) . . ? C3 N2 C1 111.9(3) . . ? C2 N2 C1 108.4(4) . . ? C3 N2 Cu2 117.7(2) . . ? C2 N2 Cu2 103.8(2) . . ? C1 N2 Cu2 107.7(3) . . ? C18 N3 O4 110.7(3) . . ? C18 N3 Cu3 131.6(3) . . ? O4 N3 Cu3 117.2(2) . . ? C12 N4 C10 111.4(3) . . ? C12 N4 C11 107.7(3) . . ? C10 N4 C11 108.2(3) . . ? C12 N4 Cu3 119.0(2) . . ? C10 N4 Cu3 105.8(2) . . ? C11 N4 Cu3 104.1(2) . . ? C9 O1 Cu3 112.4(2) . 7_665 ? N1 O2 Cu1 118.4(2) . . ? N1 O2 Cu3 113.6(2) . 7_665 ? Cu1 O2 Cu3 118.06(12) . 7_665 ? C18 O3 Cu2 113.0(2) . . ? N3 O4 Cu1 119.25(19) . . ? N3 O4 Cu2 112.40(18) . . ? Cu1 O4 Cu2 114.83(13) . . ? C19 O5 Cu3 118.4(2) . . ? C19 O5 H5 120.8 . . ? Cu3 O5 H5 120.8 . . ? C20 O10 Cu2 132.5(3) . . ? C20 O10 H10 113.8 . . ? Cu2 O10 H10 113.8 . . ? N2 C1 H1A 109.5 . . ? N2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 C8 119.1(4) . . ? C4 C3 N2 119.1(3) . . ? C8 C3 N2 121.7(3) . . ? C5 C4 C3 121.4(4) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C6 C5 C4 120.3(4) . . ? C6 C5 H5A 119.9 . . ? C4 C5 H5A 119.9 . . ? C5 C6 C7 119.1(4) . . ? C5 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C6 C7 C8 121.7(4) . . ? C6 C7 H7 119.2 . . ? C8 C7 H7 119.2 . . ? C3 C8 C7 118.5(3) . . ? C3 C8 C9 126.4(4) . . ? C7 C8 C9 115.1(3) . . ? N1 C9 O1 122.0(4) . . ? N1 C9 C8 119.6(4) . . ? O1 C9 C8 118.4(3) . . ? N4 C10 H10A 109.5 . . ? N4 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? N4 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N4 C11 H11A 109.5 . . ? N4 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N4 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 119.2(4) . . ? C13 C12 N4 119.8(4) . . ? C17 C12 N4 120.9(3) . . ? C12 C13 C14 122.1(4) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C15 C14 C13 119.7(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.2(4) . . ? C14 C15 H15 120.4 . . ? C16 C15 H15 120.4 . . ? C15 C16 C17 122.4(4) . . ? C15 C16 H16 118.8 . . ? C17 C16 H16 118.8 . . ? C16 C17 C12 117.3(4) . . ? C16 C17 C18 115.3(4) . . ? C12 C17 C18 127.4(3) . . ? O3 C18 N3 121.4(4) . . ? O3 C18 C17 119.2(3) . . ? N3 C18 C17 119.3(3) . . ? O5 C19 H19A 109.5 . . ? O5 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O5 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O10 C20 H20A 109.5 . . ? O10 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O10 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.597 _refine_diff_density_min -0.652 _refine_diff_density_rms 0.100 _database_code_depnum_ccdc_archive 'CCDC 885549' ####################################################################### # # 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_cmd165a3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu5(L)4(py)2](ClO4)2.py' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C51 H55 Cl2 Cu5 N11 O16' _chemical_formula_weight 1466.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 11.283(2) _cell_length_b 11.482(2) _cell_length_c 13.688(3) _cell_angle_alpha 72.42(3) _cell_angle_beta 80.58(3) _cell_angle_gamma 61.80(3) _cell_volume 1489.4(5) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.635 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 745 _exptl_absorpt_coefficient_mu 1.921 _cell_measurement_theta_max 25.35 _cell_measurement_theta_min 2.9032 _cell_measurement_reflns_used 7252 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_T_min 0.92903 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 10948 _diffrn_reflns_av_R_equivalents 0.0162 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.9032 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 -0.0261668000 _diffrn_orient_matrix_UB_12 -0.0336166000 _diffrn_orient_matrix_UB_13 -0.0194985000 _diffrn_orient_matrix_UB_21 -0.0396062000 _diffrn_orient_matrix_UB_22 0.0628719000 _diffrn_orient_matrix_UB_23 -0.0346115000 _diffrn_orient_matrix_UB_31 0.0532694000 _diffrn_orient_matrix_UB_32 -0.0134918000 _diffrn_orient_matrix_UB_33 -0.0371274000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -37.00 52.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -14.4216 37.0000 -30.0000 89 #__ type_ start__ end____ width___ exp.time_ 2 omega -22.00 14.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - -14.4216 -77.0000 -60.0000 36 #__ type_ start__ end____ width___ exp.time_ 3 omega -7.00 93.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 22.8591 77.0000 -180.0000 100 #__ type_ start__ end____ width___ exp.time_ 4 omega -4.00 31.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 22.8591 77.0000 -60.0000 35 #__ type_ start__ end____ width___ exp.time_ 5 omega -45.00 45.00 1.0000 60.0000 omega____ theta____ kappa____ phi______ frames - 22.8591 -63.0000 50.0000 90 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(2) _reflns_number_total 5443 _reflns_number_gt 4757 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0511P)^2^+4.7096P] 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 5443 _refine_ls_number_parameters 386 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1152 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.073 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.5000 0.0000 0.01658(16) Uani 1 2 d S . . Cu2 Cu 0.11615(5) 0.48447(4) 0.21139(3) 0.01815(13) Uani 1 1 d . . . Cu3 Cu 0.15023(4) 0.17564(4) 0.04229(3) 0.01749(13) Uani 1 1 d . . . Cl1 Cl 0.73192(11) 0.58064(12) 0.19358(9) 0.0339(3) Uani 1 1 d . . . O1 O 0.0560(3) 0.5836(2) 0.07270(19) 0.0189(5) Uani 1 1 d . . . O2 O 0.0696(3) 0.3286(2) 0.10422(19) 0.0181(5) Uani 1 1 d . . . O3 O 0.2898(3) 0.1114(3) 0.1364(2) 0.0228(6) Uani 1 1 d . . . O4 O -0.0618(3) 0.3322(3) -0.2213(2) 0.0228(6) Uani 1 1 d . . . O5 O 0.7598(4) 0.6321(4) 0.0862(3) 0.0502(9) Uani 1 1 d . . . O6 O 0.6123(5) 0.6819(4) 0.2262(4) 0.0813(17) Uani 1 1 d . . . O7 O 0.7135(5) 0.4648(4) 0.2049(4) 0.0701(13) Uani 1 1 d . . . O8 O 0.8423(5) 0.5482(6) 0.2508(3) 0.0704(14) Uani 1 1 d . . . N1 N 0.1595(3) 0.3180(3) 0.1713(2) 0.0175(6) Uani 1 1 d . . . N2 N 0.3570(3) 0.4111(3) 0.1815(3) 0.0235(7) Uani 1 1 d . . . N3 N 0.1321(3) 0.4032(3) 0.3634(2) 0.0224(7) Uani 1 1 d . . . N4 N 0.2473(3) 0.0099(3) -0.0188(2) 0.0205(7) Uani 1 1 d . . . N5 N 0.0191(3) 0.2749(3) -0.0627(2) 0.0182(6) Uani 1 1 d . . . C1 C 0.2700(4) 0.2046(4) 0.1807(3) 0.0182(8) Uani 1 1 d . . . C2 C 0.3787(4) 0.1766(4) 0.2458(3) 0.0210(8) Uani 1 1 d . . . C3 C 0.4432(4) 0.0438(4) 0.3078(3) 0.0273(9) Uani 1 1 d . . . H3 H 0.4166 -0.0227 0.3062 0.033 Uiso 1 1 calc R . . C4 C 0.5456(5) 0.0070(5) 0.3716(4) 0.0386(11) Uani 1 1 d . . . H4 H 0.5867 -0.0829 0.4152 0.046 Uiso 1 1 calc R . . C5 C 0.5869(5) 0.1025(5) 0.3712(4) 0.0428(12) Uani 1 1 d . . . H5 H 0.6572 0.0778 0.4146 0.051 Uiso 1 1 calc R . . C6 C 0.5274(4) 0.2331(5) 0.3088(4) 0.0351(10) Uani 1 1 d . . . H6 H 0.5589 0.2967 0.3084 0.042 Uiso 1 1 calc R . . C7 C 0.4221(4) 0.2737(4) 0.2462(3) 0.0232(8) Uani 1 1 d . . . C8 C 0.3840(4) 0.4158(4) 0.0712(3) 0.0287(9) Uani 1 1 d . . . H8A H 0.4779 0.3975 0.0539 0.043 Uiso 1 1 calc R . . H8B H 0.3244 0.5066 0.0303 0.043 Uiso 1 1 calc R . . H8C H 0.3676 0.3464 0.0563 0.043 Uiso 1 1 calc R . . C9 C 0.3884(5) 0.5107(5) 0.2036(4) 0.0363(11) Uani 1 1 d . . . H9A H 0.3762 0.5043 0.2773 0.055 Uiso 1 1 calc R . . H9B H 0.3281 0.6031 0.1656 0.055 Uiso 1 1 calc R . . H9C H 0.4819 0.4911 0.1827 0.055 Uiso 1 1 calc R . . C10 C 0.1061(4) 0.2974(4) 0.4097(3) 0.0283(9) Uani 1 1 d . . . H10 H 0.0815 0.2584 0.3692 0.034 Uiso 1 1 calc R . . C11 C 0.1136(5) 0.2421(5) 0.5149(3) 0.0364(11) Uani 1 1 d . . . H11 H 0.0935 0.1673 0.5459 0.044 Uiso 1 1 calc R . . C12 C 0.1505(5) 0.2974(5) 0.5735(3) 0.0380(12) Uani 1 1 d . . . H12 H 0.1566 0.2612 0.6458 0.046 Uiso 1 1 calc R . . C13 C 0.1785(4) 0.4057(5) 0.5261(3) 0.0341(10) Uani 1 1 d . . . H13 H 0.2053 0.4449 0.5650 0.041 Uiso 1 1 calc R . . C14 C 0.1674(4) 0.4565(4) 0.4217(3) 0.0283(9) Uani 1 1 d . . . H14 H 0.1854 0.5325 0.3894 0.034 Uiso 1 1 calc R . . C15 C 0.0073(4) 0.2421(4) -0.1427(3) 0.0183(7) Uani 1 1 d . . . C16 C 0.0640(4) 0.0948(4) -0.1403(3) 0.0204(8) Uani 1 1 d . . . C17 C 0.0022(4) 0.0668(4) -0.2042(3) 0.0276(9) Uani 1 1 d . . . H17 H -0.0647 0.1405 -0.2494 0.033 Uiso 1 1 calc R . . C18 C 0.0363(5) -0.0674(5) -0.2034(4) 0.0341(10) Uani 1 1 d . . . H18 H -0.0084 -0.0848 -0.2463 0.041 Uiso 1 1 calc R . . C19 C 0.1352(5) -0.1737(4) -0.1399(4) 0.0334(10) Uani 1 1 d . . . H19 H 0.1590 -0.2654 -0.1385 0.040 Uiso 1 1 calc R . . C20 C 0.2001(4) -0.1480(4) -0.0781(3) 0.0291(9) Uani 1 1 d . . . H20 H 0.2686 -0.2227 -0.0347 0.035 Uiso 1 1 calc R . . C21 C 0.1675(4) -0.0144(4) -0.0776(3) 0.0207(8) Uani 1 1 d . . . C22 C 0.3470(4) 0.0453(4) -0.0923(3) 0.0298(9) Uani 1 1 d . . . H22A H 0.4080 -0.0327 -0.1202 0.045 Uiso 1 1 calc R . . H22B H 0.3991 0.0671 -0.0563 0.045 Uiso 1 1 calc R . . H22C H 0.2991 0.1247 -0.1485 0.045 Uiso 1 1 calc R . . C23 C 0.3244(5) -0.1130(4) 0.0639(3) 0.0316(10) Uani 1 1 d . . . H23A H 0.2629 -0.1461 0.1076 0.047 Uiso 1 1 calc R . . H23B H 0.3680 -0.0885 0.1053 0.047 Uiso 1 1 calc R . . H23C H 0.3930 -0.1851 0.0331 0.047 Uiso 1 1 calc R . . N31 N 0.7959(13) 0.2518(13) 0.4302(10) 0.080(3) Uiso 0.50 1 d PD . . C30 C 0.8478(17) 0.1402(18) 0.4971(13) 0.091(5) Uiso 0.50 1 d PD . . H30 H 0.9265 0.0629 0.4848 0.109 Uiso 0.50 1 calc PR . . C33 C 0.6714(14) 0.2397(15) 0.6171(11) 0.066(3) Uiso 0.50 1 d PD . . H33 H 0.6324 0.2342 0.6843 0.079 Uiso 0.50 1 calc PR . . C32 C 0.7629(14) 0.1417(15) 0.6117(11) 0.068(4) Uiso 0.50 1 d PD . . H32 H 0.7913 0.0634 0.6686 0.082 Uiso 0.50 1 calc PR . . C35 C 0.6807(19) 0.350(2) 0.4679(15) 0.096(5) Uiso 0.50 1 d PD . . H35 H 0.6372 0.4375 0.4221 0.115 Uiso 0.50 1 calc PR . . C34 C 0.622(3) 0.329(3) 0.570(2) 0.132(8) Uiso 0.50 1 d PD . . H34 H 0.5405 0.3977 0.5902 0.158 Uiso 0.50 1 calc PR . . 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 0.0193(3) 0.0121(3) 0.0152(3) -0.0044(2) -0.0049(2) -0.0026(3) Cu2 0.0217(3) 0.0150(2) 0.0154(2) -0.00526(17) -0.00464(17) -0.00438(19) Cu3 0.0192(2) 0.0118(2) 0.0179(2) -0.00498(17) -0.00334(17) -0.00258(18) Cl1 0.0362(6) 0.0390(6) 0.0374(6) -0.0207(5) 0.0067(5) -0.0215(5) O1 0.0214(13) 0.0109(12) 0.0196(13) -0.0063(10) -0.0065(10) -0.0002(10) O2 0.0199(13) 0.0148(12) 0.0179(13) -0.0053(10) -0.0057(10) -0.0043(10) O3 0.0228(14) 0.0142(13) 0.0257(15) -0.0066(11) -0.0064(11) -0.0011(11) O4 0.0281(15) 0.0193(13) 0.0203(14) -0.0076(11) -0.0070(11) -0.0068(12) O5 0.050(2) 0.077(3) 0.0293(18) -0.0159(18) 0.0008(15) -0.033(2) O6 0.083(3) 0.039(2) 0.086(3) -0.017(2) 0.046(3) -0.013(2) O7 0.075(3) 0.051(2) 0.107(4) -0.034(2) 0.011(3) -0.043(2) O8 0.074(3) 0.148(4) 0.028(2) -0.025(2) 0.0035(18) -0.080(3) N1 0.0183(15) 0.0178(15) 0.0150(15) -0.0042(12) -0.0063(12) -0.0051(13) N2 0.0229(17) 0.0207(17) 0.0259(18) -0.0051(14) -0.0029(14) -0.0089(14) N3 0.0218(17) 0.0213(16) 0.0183(16) -0.0069(13) -0.0024(13) -0.0034(14) N4 0.0206(16) 0.0145(15) 0.0237(17) -0.0064(13) -0.0002(13) -0.0049(13) N5 0.0209(16) 0.0105(14) 0.0191(16) -0.0062(12) -0.0020(12) -0.0019(12) C1 0.0200(18) 0.0149(17) 0.0159(18) -0.0018(14) -0.0004(14) -0.0060(15) C2 0.0175(18) 0.0211(19) 0.0172(19) -0.0056(15) -0.0011(14) -0.0023(15) C3 0.027(2) 0.021(2) 0.023(2) -0.0020(16) -0.0056(16) -0.0030(17) C4 0.034(2) 0.032(2) 0.028(2) 0.0029(19) -0.0126(19) 0.000(2) C5 0.033(3) 0.047(3) 0.040(3) -0.005(2) -0.021(2) -0.009(2) C6 0.029(2) 0.037(3) 0.040(3) -0.011(2) -0.0092(19) -0.012(2) C7 0.0182(19) 0.025(2) 0.022(2) -0.0071(16) -0.0021(15) -0.0051(16) C8 0.026(2) 0.027(2) 0.028(2) -0.0027(17) 0.0023(17) -0.0111(18) C9 0.034(2) 0.031(2) 0.050(3) -0.012(2) -0.007(2) -0.018(2) C10 0.030(2) 0.027(2) 0.024(2) -0.0084(17) 0.0013(17) -0.0093(18) C11 0.040(3) 0.031(2) 0.026(2) -0.0019(18) 0.0026(19) -0.010(2) C12 0.032(2) 0.041(3) 0.017(2) -0.0045(19) -0.0013(17) 0.001(2) C13 0.026(2) 0.043(3) 0.025(2) -0.016(2) -0.0069(17) -0.003(2) C14 0.025(2) 0.031(2) 0.024(2) -0.0123(17) -0.0026(16) -0.0050(18) C15 0.0166(18) 0.0192(18) 0.0204(19) -0.0065(15) -0.0001(14) -0.0083(15) C16 0.0225(19) 0.0196(19) 0.021(2) -0.0095(15) 0.0044(15) -0.0102(16) C17 0.031(2) 0.027(2) 0.030(2) -0.0123(18) -0.0002(17) -0.0149(18) C18 0.042(3) 0.032(2) 0.042(3) -0.021(2) 0.002(2) -0.021(2) C19 0.043(3) 0.021(2) 0.042(3) -0.0158(19) 0.007(2) -0.018(2) C20 0.031(2) 0.018(2) 0.036(2) -0.0109(17) 0.0039(18) -0.0083(18) C21 0.0228(19) 0.0188(19) 0.022(2) -0.0090(15) 0.0066(15) -0.0102(16) C22 0.025(2) 0.032(2) 0.033(2) -0.0135(19) 0.0058(17) -0.0122(19) C23 0.040(2) 0.0139(19) 0.032(2) -0.0064(17) -0.0096(19) -0.0013(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.914(3) 2_565 ? Cu1 O1 1.914(3) . ? Cu1 O2 1.933(3) . ? Cu1 O2 1.933(3) 2_565 ? Cu2 O1 1.936(3) . ? Cu2 O4 1.937(3) 2_565 ? Cu2 N1 1.963(3) . ? Cu2 N3 2.006(3) . ? Cu2 N2 2.438(3) . ? Cu3 N5 1.914(3) . ? Cu3 O3 1.917(3) . ? Cu3 O2 1.941(3) . ? Cu3 N4 2.052(3) . ? Cl1 O7 1.401(4) . ? Cl1 O6 1.417(4) . ? Cl1 O8 1.418(4) . ? Cl1 O5 1.453(4) . ? O1 N5 1.407(4) 2_565 ? O2 N1 1.418(4) . ? O3 C1 1.297(5) . ? O4 C15 1.294(5) . ? O4 Cu2 1.937(3) 2_565 ? N1 C1 1.298(5) . ? N2 C7 1.444(5) . ? N2 C9 1.467(5) . ? N2 C8 1.481(5) . ? N3 C10 1.332(6) . ? N3 C14 1.341(5) . ? N4 C21 1.464(5) . ? N4 C23 1.493(5) . ? N4 C22 1.503(5) . ? N5 C15 1.305(5) . ? N5 O1 1.407(4) 2_565 ? C1 C2 1.489(5) . ? C2 C3 1.395(5) . ? C2 C7 1.415(6) . ? C3 C4 1.386(6) . ? C3 H3 0.9500 . ? C4 C5 1.377(7) . ? C4 H4 0.9500 . ? C5 C6 1.376(7) . ? C5 H5 0.9500 . ? C6 C7 1.390(6) . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.385(6) . ? C10 H10 0.9500 . ? C11 C12 1.374(7) . ? C11 H11 0.9500 . ? C12 C13 1.373(7) . ? C12 H12 0.9500 . ? C13 C14 1.373(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.491(5) . ? C16 C17 1.392(6) . ? C16 C21 1.402(6) . ? C17 C18 1.397(6) . ? C17 H17 0.9500 . ? C18 C19 1.371(7) . ? C18 H18 0.9500 . ? C19 C20 1.378(6) . ? C19 H19 0.9500 . ? C20 C21 1.400(5) . ? C20 H20 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N31 C30 1.26(2) . ? N31 C35 1.40(2) . ? C30 C32 1.70(2) . ? C30 H30 0.9500 . ? C33 C34 0.98(2) . ? C33 C32 1.124(18) . ? C33 H33 0.9500 . ? C32 H32 0.9500 . ? C35 C34 1.45(3) . ? C35 H35 0.9500 . ? C34 H34 0.9500 . ? 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 O1 180.00(12) 2_565 . ? O1 Cu1 O2 88.33(11) 2_565 . ? O1 Cu1 O2 91.67(11) . . ? O1 Cu1 O2 91.67(11) 2_565 2_565 ? O1 Cu1 O2 88.33(11) . 2_565 ? O2 Cu1 O2 180.0(2) . 2_565 ? O1 Cu2 O4 81.34(11) . 2_565 ? O1 Cu2 N1 86.58(12) . . ? O4 Cu2 N1 167.92(12) 2_565 . ? O1 Cu2 N3 166.46(12) . . ? O4 Cu2 N3 93.90(13) 2_565 . ? N1 Cu2 N3 97.94(13) . . ? O1 Cu2 N2 99.19(12) . . ? O4 Cu2 N2 99.03(12) 2_565 . ? N1 Cu2 N2 82.62(12) . . ? N3 Cu2 N2 94.06(13) . . ? N5 Cu3 O3 167.01(13) . . ? N5 Cu3 O2 90.78(12) . . ? O3 Cu3 O2 82.14(11) . . ? N5 Cu3 N4 92.67(13) . . ? O3 Cu3 N4 94.17(12) . . ? O2 Cu3 N4 176.20(12) . . ? O7 Cl1 O6 108.8(3) . . ? O7 Cl1 O8 111.1(3) . . ? O6 Cl1 O8 110.4(3) . . ? O7 Cl1 O5 108.9(3) . . ? O6 Cl1 O5 109.5(3) . . ? O8 Cl1 O5 108.2(2) . . ? N5 O1 Cu1 118.5(2) 2_565 . ? N5 O1 Cu2 111.71(19) 2_565 . ? Cu1 O1 Cu2 117.47(13) . . ? N1 O2 Cu1 114.0(2) . . ? N1 O2 Cu3 111.25(19) . . ? Cu1 O2 Cu3 110.52(12) . . ? C1 O3 Cu3 111.3(2) . . ? C15 O4 Cu2 110.7(2) . 2_565 ? C1 N1 O2 111.9(3) . . ? C1 N1 Cu2 130.2(3) . . ? O2 N1 Cu2 116.6(2) . . ? C7 N2 C9 115.0(3) . . ? C7 N2 C8 112.3(3) . . ? C9 N2 C8 108.8(3) . . ? C7 N2 Cu2 105.8(2) . . ? C9 N2 Cu2 107.9(3) . . ? C8 N2 Cu2 106.6(2) . . ? C10 N3 C14 118.1(4) . . ? C10 N3 Cu2 121.6(3) . . ? C14 N3 Cu2 120.2(3) . . ? C21 N4 C23 112.9(3) . . ? C21 N4 C22 107.3(3) . . ? C23 N4 C22 107.7(3) . . ? C21 N4 Cu3 117.6(2) . . ? C23 N4 Cu3 108.4(2) . . ? C22 N4 Cu3 102.0(2) . . ? C15 N5 O1 111.3(3) . 2_565 ? C15 N5 Cu3 130.3(3) . . ? O1 N5 Cu3 116.2(2) 2_565 . ? O3 C1 N1 122.6(3) . . ? O3 C1 C2 117.6(3) . . ? N1 C1 C2 119.8(3) . . ? C3 C2 C7 119.0(4) . . ? C3 C2 C1 116.6(4) . . ? C7 C2 C1 124.5(3) . . ? C4 C3 C2 121.2(4) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? C5 C4 C3 119.2(4) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C6 C5 C4 120.8(4) . . ? C6 C5 H5 119.6 . . ? C4 C5 H5 119.6 . . ? C5 C6 C7 121.2(5) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C6 C7 C2 118.6(4) . . ? C6 C7 N2 121.9(4) . . ? C2 C7 N2 119.5(3) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 C11 122.3(4) . . ? N3 C10 H10 118.8 . . ? C11 C10 H10 118.8 . . ? C12 C11 C10 118.9(4) . . ? C12 C11 H11 120.5 . . ? C10 C11 H11 120.5 . . ? C13 C12 C11 119.0(4) . . ? C13 C12 H12 120.5 . . ? C11 C12 H12 120.5 . . ? C12 C13 C14 119.1(4) . . ? C12 C13 H13 120.5 . . ? C14 C13 H13 120.5 . . ? N3 C14 C13 122.6(4) . . ? N3 C14 H14 118.7 . . ? C13 C14 H14 118.7 . . ? O4 C15 N5 122.6(3) . . ? O4 C15 C16 118.0(3) . . ? N5 C15 C16 119.1(3) . . ? C17 C16 C21 118.9(4) . . ? C17 C16 C15 115.0(3) . . ? C21 C16 C15 126.0(3) . . ? C16 C17 C18 121.5(4) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C19 C18 C17 119.2(4) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.2(4) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C19 C20 C21 121.7(4) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C20 C21 C16 118.5(4) . . ? C20 C21 N4 120.2(4) . . ? C16 C21 N4 121.1(3) . . ? N4 C22 H22A 109.5 . . ? N4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N4 C23 H23A 109.5 . . ? N4 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? N4 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C30 N31 C35 112.1(16) . . ? N31 C30 C32 113.2(15) . . ? N31 C30 H30 123.4 . . ? C32 C30 H30 123.4 . . ? C34 C33 C32 136(3) . . ? C34 C33 H33 111.9 . . ? C32 C33 H33 111.9 . . ? C33 C32 C30 116.8(15) . . ? C33 C32 H32 121.6 . . ? C30 C32 H32 121.6 . . ? N31 C35 C34 126.1(19) . . ? N31 C35 H35 117.0 . . ? C34 C35 H35 117.0 . . ? C33 C34 C35 115(3) . . ? C33 C34 H34 122.3 . . ? C35 C34 H34 122.3 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.042 _refine_diff_density_min -0.398 _refine_diff_density_rms 0.105 _database_code_depnum_ccdc_archive 'CCDC 885550' ####################################################################### # # 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_cmd168a3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu5(L)4(py)6](ClO4)2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H70 Cl2 Cu5 N14 O16' _chemical_formula_weight 1703.96 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3067(3) _cell_length_b 12.7372(5) _cell_length_c 13.2511(4) _cell_angle_alpha 97.753(3) _cell_angle_beta 104.385(3) _cell_angle_gamma 103.130(3) _cell_volume 1762.79(10) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _exptl_crystal_description Block _exptl_crystal_colour Green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 871 _exptl_absorpt_coefficient_mu 1.637 _cell_measurement_theta_max 25.35 _cell_measurement_theta_min 2.8764 _cell_measurement_reflns_used 8503 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_T_min 0.78649 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 13974 _diffrn_reflns_av_R_equivalents 0.0185 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.8764 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 -0.0021765000 _diffrn_orient_matrix_UB_12 -0.0500633000 _diffrn_orient_matrix_UB_13 0.0182460000 _diffrn_orient_matrix_UB_21 -0.0672571000 _diffrn_orient_matrix_UB_22 -0.0142394000 _diffrn_orient_matrix_UB_23 -0.0169024000 _diffrn_orient_matrix_UB_31 -0.0000234000 _diffrn_orient_matrix_UB_32 -0.0264761000 _diffrn_orient_matrix_UB_33 -0.0506564000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -11.00 16.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - -14.4216 -77.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 2 omega -42.00 53.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 22.8591 -77.0000 60.0000 95 #__ type_ start__ end____ width___ exp.time_ 3 omega -1.00 92.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 22.8591 77.0000 -180.0000 93 #__ type_ start__ end____ width___ exp.time_ 4 omega 6.00 88.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 22.8591 77.0000 -30.0000 82 #__ type_ start__ end____ width___ exp.time_ 5 omega 10.00 88.00 1.0000 20.0000 omega____ theta____ kappa____ phi______ frames - 22.8591 37.0000 -30.0000 78 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(2) _reflns_number_total 6450 _reflns_number_gt 5592 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0317P)^2^+0.8757P] 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 6450 _refine_ls_number_parameters 467 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0267 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0644 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.5000 0.5000 0.5000 0.01120(9) Uani 1 2 d S . . Cu2 Cu 0.52020(2) 0.32998(2) 0.66390(2) 0.01334(8) Uani 1 1 d . . . Cu3 Cu 0.75587(2) 0.67595(2) 0.66606(2) 0.01152(7) Uani 1 1 d . . . Cl1 Cl 0.62838(5) 0.27474(5) 0.10963(4) 0.02077(13) Uani 1 1 d . . . N1 N 0.37560(16) 0.29450(14) 0.53431(14) 0.0123(4) Uani 1 1 d . . . N2 N 0.33188(18) 0.37153(15) 0.73592(15) 0.0177(4) Uani 1 1 d . . . N3 N 0.66995(16) 0.54699(15) 0.71086(14) 0.0132(4) Uani 1 1 d . . . N4 N 0.93001(16) 0.66507(15) 0.75883(14) 0.0137(4) Uani 1 1 d . . . N5 N 0.75245(18) 0.82009(16) 0.77776(16) 0.0207(4) Uani 1 1 d . . . N6 N 0.49744(17) 0.17898(15) 0.69501(14) 0.0148(4) Uani 1 1 d . . . N7 N 0.68187(18) 0.28826(16) 0.57365(15) 0.0201(4) Uani 1 1 d . . . O1 O 0.39913(13) 0.34817(12) 0.45117(11) 0.0130(3) Uani 1 1 d . . . O2 O 0.55604(14) 0.47820(12) 0.63933(12) 0.0157(3) Uani 1 1 d . . . O3 O 0.65891(14) 0.39913(12) 0.79226(12) 0.0153(3) Uani 1 1 d . . . O4 O 0.16953(14) 0.24366(13) 0.43038(12) 0.0161(3) Uani 1 1 d . . . O5 O 0.60396(18) 0.28220(15) 0.21111(13) 0.0298(4) Uani 1 1 d . . . O6 O 0.64625(19) 0.16806(15) 0.07786(15) 0.0376(5) Uani 1 1 d . . . O7 O 0.52318(18) 0.29001(18) 0.03301(14) 0.0379(5) Uani 1 1 d . . . O8 O 0.74111(18) 0.35880(16) 0.11822(17) 0.0377(5) Uani 1 1 d . . . C1 C 0.2559(2) 0.24853(17) 0.51776(17) 0.0134(5) Uani 1 1 d . . . C2 C 0.2162(2) 0.20113(19) 0.60519(18) 0.0158(5) Uani 1 1 d . . . C3 C 0.1438(2) 0.0926(2) 0.58186(19) 0.0223(5) Uani 1 1 d . . . H3 H 0.1178 0.0522 0.5107 0.027 Uiso 1 1 calc R . . C4 C 0.1088(2) 0.0418(2) 0.6598(2) 0.0293(6) Uani 1 1 d . . . H4 H 0.0603 -0.0330 0.6426 0.035 Uiso 1 1 calc R . . C5 C 0.1451(2) 0.1008(2) 0.7629(2) 0.0290(6) Uani 1 1 d . . . H5 H 0.1214 0.0665 0.8170 0.035 Uiso 1 1 calc R . . C6 C 0.2155(2) 0.2097(2) 0.78782(19) 0.0235(5) Uani 1 1 d . . . H6 H 0.2386 0.2496 0.8589 0.028 Uiso 1 1 calc R . . C7 C 0.2536(2) 0.26218(19) 0.71064(18) 0.0165(5) Uani 1 1 d . . . C8 C 0.2762(2) 0.4488(2) 0.6793(2) 0.0244(6) Uani 1 1 d . . . H8A H 0.2388 0.4150 0.6036 0.037 Uiso 1 1 calc R . . H8B H 0.3426 0.5166 0.6875 0.037 Uiso 1 1 calc R . . H8C H 0.2103 0.4662 0.7092 0.037 Uiso 1 1 calc R . . C9 C 0.3909(2) 0.4213(2) 0.84879(19) 0.0248(6) Uani 1 1 d . . . H9A H 0.3260 0.4364 0.8813 0.037 Uiso 1 1 calc R . . H9B H 0.4551 0.4902 0.8562 0.037 Uiso 1 1 calc R . . H9C H 0.4312 0.3704 0.8845 0.037 Uiso 1 1 calc R . . C10 C 0.7133(2) 0.49738(18) 0.78716(16) 0.0122(4) Uani 1 1 d . . . C11 C 0.8273(2) 0.56193(18) 0.87526(17) 0.0131(5) Uani 1 1 d . . . C12 C 0.8307(2) 0.53745(19) 0.97566(17) 0.0172(5) Uani 1 1 d . . . H12 H 0.7636 0.4815 0.9829 0.021 Uiso 1 1 calc R . . C13 C 0.9302(2) 0.5935(2) 1.06422(18) 0.0203(5) Uani 1 1 d . . . H13 H 0.9304 0.5777 1.1323 0.024 Uiso 1 1 calc R . . C14 C 1.0290(2) 0.6723(2) 1.05298(19) 0.0226(5) Uani 1 1 d . . . H14 H 1.0984 0.7102 1.1135 0.027 Uiso 1 1 calc R . . C15 C 1.0285(2) 0.69684(19) 0.95430(18) 0.0189(5) Uani 1 1 d . . . H15 H 1.0976 0.7514 0.9479 0.023 Uiso 1 1 calc R . . C16 C 0.9278(2) 0.64259(18) 0.86413(17) 0.0137(5) Uani 1 1 d . . . C17 C 0.9573(2) 0.5710(2) 0.69601(18) 0.0190(5) Uani 1 1 d . . . H17A H 1.0427 0.5662 0.7305 0.028 Uiso 1 1 calc R . . H17B H 0.9522 0.5832 0.6238 0.028 Uiso 1 1 calc R . . H17C H 0.8950 0.5022 0.6927 0.028 Uiso 1 1 calc R . . C18 C 1.0283(2) 0.7673(2) 0.76471(19) 0.0211(5) Uani 1 1 d . . . H18A H 1.0153 0.8294 0.8089 0.032 Uiso 1 1 calc R . . H18B H 1.0218 0.7815 0.6930 0.032 Uiso 1 1 calc R . . H18C H 1.1126 0.7583 0.7962 0.032 Uiso 1 1 calc R . . C19 C 0.7040(2) 0.8076(2) 0.85869(19) 0.0238(5) Uani 1 1 d . . . H19 H 0.6619 0.7353 0.8627 0.029 Uiso 1 1 calc R . . C20 C 0.7118(3) 0.8946(2) 0.9375(2) 0.0369(7) Uani 1 1 d . . . H20 H 0.6763 0.8822 0.9941 0.044 Uiso 1 1 calc R . . C21 C 0.7717(3) 0.9984(3) 0.9315(3) 0.0516(10) Uani 1 1 d . . . H21 H 0.7787 1.0597 0.9844 0.062 Uiso 1 1 calc R . . C22 C 0.8216(2) 1.01344(16) 0.84839(19) 0.0560(10) Uani 1 1 d . . . H22 H 0.8638 1.0851 0.8430 0.067 Uiso 1 1 calc R . . C23 C 0.8093(2) 0.92234(16) 0.77258(19) 0.0348(7) Uani 1 1 d . . . H23 H 0.8428 0.9331 0.7145 0.042 Uiso 1 1 calc R . . C24 C 0.4587(2) 0.09121(19) 0.61538(19) 0.0205(5) Uani 1 1 d . . . H24 H 0.4461 0.1025 0.5445 0.025 Uiso 1 1 calc R . . C25 C 0.4362(3) -0.0151(2) 0.6322(2) 0.0305(6) Uani 1 1 d . . . H25 H 0.4096 -0.0757 0.5739 0.037 Uiso 1 1 calc R . . C26 C 0.4525(3) -0.0322(2) 0.7343(2) 0.0343(7) Uani 1 1 d . . . H26 H 0.4365 -0.1047 0.7479 0.041 Uiso 1 1 calc R . . C27 C 0.4928(3) 0.0585(2) 0.8169(2) 0.0313(6) Uani 1 1 d . . . H27 H 0.5049 0.0492 0.8883 0.038 Uiso 1 1 calc R . . C28 C 0.5153(2) 0.1619(2) 0.79470(19) 0.0209(5) Uani 1 1 d . . . H28 H 0.5445 0.2238 0.8520 0.025 Uiso 1 1 calc R . . C29 C 0.7751(2) 0.2578(2) 0.6368(2) 0.0256(6) Uani 1 1 d . . . H29 H 0.7663 0.2424 0.7031 0.031 Uiso 1 1 calc R . . C30 C 0.8830(2) 0.2475(2) 0.6106(2) 0.0300(6) Uani 1 1 d . . . H30 H 0.9467 0.2257 0.6579 0.036 Uiso 1 1 calc R . . C31 C 0.8966(2) 0.2694(2) 0.5145(2) 0.0314(6) Uani 1 1 d . . . H31 H 0.9700 0.2631 0.4942 0.038 Uiso 1 1 calc R . . C32 C 0.8012(2) 0.3008(2) 0.4479(2) 0.0285(6) Uani 1 1 d . . . H32 H 0.8079 0.3167 0.3812 0.034 Uiso 1 1 calc R . . C33 C 0.6961(2) 0.3085(2) 0.48087(19) 0.0208(5) Uani 1 1 d . . . H33 H 0.6305 0.3293 0.4347 0.025 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 0.01187(18) 0.00956(19) 0.01066(19) 0.00453(14) 0.00188(14) 0.00002(15) Cu2 0.01419(14) 0.01009(14) 0.01254(14) 0.00573(10) 0.00054(11) -0.00134(11) Cu3 0.01165(13) 0.01020(14) 0.01078(14) 0.00405(10) 0.00202(10) -0.00062(11) Cl1 0.0245(3) 0.0212(3) 0.0182(3) 0.0071(2) 0.0056(2) 0.0082(2) N1 0.0147(9) 0.0099(9) 0.0119(9) 0.0070(7) 0.0045(7) -0.0010(8) N2 0.0221(10) 0.0157(10) 0.0153(10) 0.0034(8) 0.0063(8) 0.0038(8) N3 0.0104(9) 0.0130(9) 0.0110(9) 0.0016(7) -0.0006(7) -0.0022(8) N4 0.0135(9) 0.0127(9) 0.0139(9) 0.0049(7) 0.0040(7) 0.0002(8) N5 0.0191(10) 0.0160(10) 0.0252(11) 0.0003(8) 0.0064(8) 0.0037(8) N6 0.0159(9) 0.0130(10) 0.0160(10) 0.0046(8) 0.0047(8) 0.0038(8) N7 0.0194(10) 0.0214(11) 0.0194(11) 0.0042(8) 0.0056(8) 0.0048(9) O1 0.0138(7) 0.0120(8) 0.0114(8) 0.0061(6) 0.0029(6) -0.0016(6) O2 0.0142(7) 0.0128(8) 0.0133(8) 0.0048(6) -0.0030(6) -0.0034(6) O3 0.0165(8) 0.0126(8) 0.0137(8) 0.0061(6) 0.0016(6) -0.0007(6) O4 0.0135(7) 0.0178(8) 0.0145(8) 0.0080(6) 0.0019(6) -0.0008(7) O5 0.0460(11) 0.0238(10) 0.0188(9) 0.0071(7) 0.0116(8) 0.0040(9) O6 0.0461(12) 0.0257(11) 0.0406(12) -0.0004(9) 0.0106(9) 0.0151(9) O7 0.0369(11) 0.0555(14) 0.0251(10) 0.0147(9) 0.0030(8) 0.0228(10) O8 0.0315(10) 0.0317(11) 0.0561(13) 0.0175(10) 0.0211(9) 0.0061(9) C1 0.0160(11) 0.0093(11) 0.0140(11) 0.0032(9) 0.0045(9) 0.0009(9) C2 0.0119(10) 0.0190(12) 0.0172(12) 0.0095(9) 0.0027(9) 0.0036(9) C3 0.0195(12) 0.0220(13) 0.0206(13) 0.0074(10) 0.0029(10) -0.0023(10) C4 0.0255(13) 0.0249(14) 0.0317(15) 0.0141(12) 0.0039(11) -0.0049(11) C5 0.0249(13) 0.0377(16) 0.0259(14) 0.0218(12) 0.0098(11) -0.0005(12) C6 0.0215(12) 0.0320(15) 0.0185(13) 0.0109(11) 0.0077(10) 0.0048(11) C7 0.0138(11) 0.0195(12) 0.0182(12) 0.0078(9) 0.0053(9) 0.0052(10) C8 0.0310(14) 0.0197(13) 0.0262(14) 0.0064(10) 0.0103(11) 0.0106(11) C9 0.0285(13) 0.0263(14) 0.0185(13) 0.0006(11) 0.0077(10) 0.0068(11) C10 0.0137(10) 0.0129(11) 0.0117(11) 0.0038(9) 0.0060(9) 0.0034(9) C11 0.0143(10) 0.0125(11) 0.0130(11) 0.0032(9) 0.0030(9) 0.0053(9) C12 0.0199(12) 0.0178(12) 0.0154(12) 0.0045(9) 0.0066(9) 0.0056(10) C13 0.0267(13) 0.0235(13) 0.0111(11) 0.0056(10) 0.0040(10) 0.0079(11) C14 0.0222(12) 0.0206(13) 0.0161(12) -0.0011(10) -0.0031(10) 0.0006(11) C15 0.0163(11) 0.0148(12) 0.0196(12) 0.0019(9) 0.0009(9) -0.0018(10) C16 0.0153(11) 0.0110(11) 0.0151(11) 0.0040(9) 0.0033(9) 0.0047(9) C17 0.0194(12) 0.0211(13) 0.0190(12) 0.0061(10) 0.0089(10) 0.0056(10) C18 0.0143(11) 0.0220(13) 0.0235(13) 0.0118(10) 0.0022(10) -0.0027(10) C19 0.0212(12) 0.0235(13) 0.0234(13) 0.0000(11) 0.0051(10) 0.0039(11) C20 0.0287(14) 0.0441(18) 0.0308(16) -0.0133(13) 0.0086(12) 0.0082(14) C21 0.0472(19) 0.0308(18) 0.065(2) -0.0249(16) 0.0220(17) 0.0021(15) C22 0.058(2) 0.0158(15) 0.093(3) -0.0085(16) 0.039(2) -0.0005(15) C23 0.0382(15) 0.0190(14) 0.0513(18) 0.0058(13) 0.0239(14) 0.0047(12) C24 0.0258(12) 0.0177(12) 0.0173(12) 0.0049(10) 0.0060(10) 0.0041(10) C25 0.0431(16) 0.0138(13) 0.0312(15) 0.0010(11) 0.0099(12) 0.0041(12) C26 0.0504(17) 0.0157(13) 0.0399(17) 0.0138(12) 0.0159(14) 0.0074(13) C27 0.0524(17) 0.0244(14) 0.0246(14) 0.0166(11) 0.0162(13) 0.0129(13) C28 0.0275(13) 0.0177(12) 0.0192(13) 0.0054(10) 0.0078(10) 0.0075(11) C29 0.0257(13) 0.0341(15) 0.0181(13) 0.0081(11) 0.0061(10) 0.0091(12) C30 0.0232(13) 0.0409(17) 0.0274(14) 0.0092(12) 0.0043(11) 0.0135(12) C31 0.0231(13) 0.0446(17) 0.0310(15) 0.0084(13) 0.0129(11) 0.0122(13) C32 0.0286(14) 0.0393(16) 0.0218(14) 0.0109(12) 0.0124(11) 0.0088(12) C33 0.0210(12) 0.0206(13) 0.0210(13) 0.0055(10) 0.0056(10) 0.0059(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.8773(15) . ? Cu1 O2 1.8773(15) 2_666 ? Cu1 O1 1.9373(15) 2_666 ? Cu1 O1 1.9373(15) . ? Cu2 O2 1.9283(16) . ? Cu2 O3 1.9420(15) . ? Cu2 N1 1.9714(17) . ? Cu2 N6 1.9942(19) . ? Cu2 N7 2.5317(19) . ? Cu2 N2 2.6666(19) . ? Cu3 N3 1.9543(19) . ? Cu3 O1 1.9629(14) 2_666 ? Cu3 O4 1.9721(16) 2_666 ? Cu3 N4 2.0915(17) . ? Cu3 N5 2.2115(18) . ? Cl1 O7 1.4290(18) . ? Cl1 O5 1.4337(18) . ? Cl1 O8 1.435(2) . ? Cl1 O6 1.4412(18) . ? N1 C1 1.297(3) . ? N1 O1 1.420(2) . ? N2 C7 1.415(3) . ? N2 C9 1.463(3) . ? N2 C8 1.474(3) . ? N3 C10 1.315(3) . ? N3 O2 1.408(2) . ? N4 C16 1.467(3) . ? N4 C18 1.486(3) . ? N4 C17 1.500(3) . ? N5 C19 1.332(3) . ? N5 C23 1.334(3) . ? N6 C24 1.336(3) . ? N6 C28 1.341(3) . ? N7 C33 1.330(3) . ? N7 C29 1.341(3) . ? O1 Cu3 1.9629(14) 2_666 ? O3 C10 1.282(3) . ? O4 C1 1.300(3) . ? O4 Cu3 1.9721(16) 2_666 ? C1 C2 1.494(3) . ? C2 C3 1.386(3) . ? C2 C7 1.414(3) . ? C3 C4 1.382(4) . ? C3 H3 0.9500 . ? C4 C5 1.381(4) . ? C4 H4 0.9500 . ? C5 C6 1.382(4) . ? C5 H5 0.9500 . ? C6 C7 1.397(3) . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.487(3) . ? C11 C12 1.400(3) . ? C11 C16 1.401(3) . ? C12 C13 1.380(3) . ? C12 H12 0.9500 . ? C13 C14 1.376(4) . ? C13 H13 0.9500 . ? C14 C15 1.384(3) . ? C14 H14 0.9500 . ? C15 C16 1.395(3) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.387(3) . ? C19 H19 0.9500 . ? C20 C21 1.364(5) . ? C20 H20 0.9500 . ? C21 C22 1.373(4) . ? C21 H21 0.9500 . ? C22 C23 1.385(3) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.378(3) . ? C24 H24 0.9500 . ? C25 C26 1.374(4) . ? C25 H25 0.9500 . ? C26 C27 1.383(4) . ? C26 H26 0.9500 . ? C27 C28 1.370(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.376(4) . ? C29 H29 0.9500 . ? C30 C31 1.378(4) . ? C30 H30 0.9500 . ? C31 C32 1.386(4) . ? C31 H31 0.9500 . ? C32 C33 1.383(3) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.0 . 2_666 ? O2 Cu1 O1 88.56(6) . 2_666 ? O2 Cu1 O1 91.44(6) 2_666 2_666 ? O2 Cu1 O1 91.44(6) . . ? O2 Cu1 O1 88.56(6) 2_666 . ? O1 Cu1 O1 180.0 2_666 . ? O2 Cu2 O3 81.52(6) . . ? O2 Cu2 N1 86.31(7) . . ? O3 Cu2 N1 166.80(7) . . ? O2 Cu2 N6 175.56(7) . . ? O3 Cu2 N6 94.73(7) . . ? N1 Cu2 N6 97.63(7) . . ? O2 Cu2 N7 90.69(7) . . ? O3 Cu2 N7 88.30(6) . . ? N1 Cu2 N7 96.98(7) . . ? N6 Cu2 N7 86.81(7) . . ? O2 Cu2 N2 87.74(6) . . ? O3 Cu2 N2 97.98(6) . . ? N1 Cu2 N2 76.34(7) . . ? N6 Cu2 N2 95.16(7) . . ? N7 Cu2 N2 173.22(6) . . ? N3 Cu3 O1 88.10(7) . 2_666 ? N3 Cu3 O4 155.88(7) . 2_666 ? O1 Cu3 O4 81.24(6) 2_666 2_666 ? N3 Cu3 N4 89.46(7) . . ? O1 Cu3 N4 162.65(6) 2_666 . ? O4 Cu3 N4 94.31(7) 2_666 . ? N3 Cu3 N5 105.63(8) . . ? O1 Cu3 N5 103.21(6) 2_666 . ? O4 Cu3 N5 97.87(7) 2_666 . ? N4 Cu3 N5 94.00(7) . . ? O7 Cl1 O5 109.24(11) . . ? O7 Cl1 O8 109.71(13) . . ? O5 Cl1 O8 109.04(12) . . ? O7 Cl1 O6 109.92(12) . . ? O5 Cl1 O6 109.37(12) . . ? O8 Cl1 O6 109.54(12) . . ? C1 N1 O1 112.20(17) . . ? C1 N1 Cu2 131.16(16) . . ? O1 N1 Cu2 115.06(12) . . ? C7 N2 C9 117.1(2) . . ? C7 N2 C8 114.88(18) . . ? C9 N2 C8 110.46(18) . . ? C7 N2 Cu2 97.56(12) . . ? C9 N2 Cu2 105.02(13) . . ? C8 N2 Cu2 110.49(14) . . ? C10 N3 O2 110.41(18) . . ? C10 N3 Cu3 130.01(15) . . ? O2 N3 Cu3 117.61(13) . . ? C16 N4 C18 112.64(17) . . ? C16 N4 C17 109.43(17) . . ? C18 N4 C17 107.95(17) . . ? C16 N4 Cu3 113.66(13) . . ? C18 N4 Cu3 108.08(13) . . ? C17 N4 Cu3 104.63(13) . . ? C19 N5 C23 117.4(2) . . ? C19 N5 Cu3 121.09(17) . . ? C23 N5 Cu3 121.18(15) . . ? C24 N6 C28 118.1(2) . . ? C24 N6 Cu2 120.12(16) . . ? C28 N6 Cu2 121.69(15) . . ? C33 N7 C29 117.0(2) . . ? C33 N7 Cu2 128.59(15) . . ? C29 N7 Cu2 113.50(16) . . ? N1 O1 Cu1 113.92(11) . . ? N1 O1 Cu3 112.04(11) . 2_666 ? Cu1 O1 Cu3 114.79(7) . 2_666 ? N3 O2 Cu1 120.85(13) . . ? N3 O2 Cu2 112.53(12) . . ? Cu1 O2 Cu2 118.58(7) . . ? C10 O3 Cu2 110.46(13) . . ? C1 O4 Cu3 110.89(14) . 2_666 ? N1 C1 O4 123.4(2) . . ? N1 C1 C2 117.70(19) . . ? O4 C1 C2 118.92(19) . . ? C3 C2 C7 119.5(2) . . ? C3 C2 C1 118.3(2) . . ? C7 C2 C1 122.1(2) . . ? C4 C3 C2 121.5(2) . . ? C4 C3 H3 119.3 . . ? C2 C3 H3 119.3 . . ? C5 C4 C3 119.3(2) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 120.3(2) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C7 121.4(2) . . ? C5 C6 H6 119.3 . . ? C7 C6 H6 119.3 . . ? C6 C7 N2 122.1(2) . . ? C6 C7 C2 118.0(2) . . ? N2 C7 C2 119.8(2) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 N3 123.57(19) . . ? O3 C10 C11 118.68(19) . . ? N3 C10 C11 117.6(2) . . ? C12 C11 C16 119.5(2) . . ? C12 C11 C10 115.4(2) . . ? C16 C11 C10 125.0(2) . . ? C13 C12 C11 121.0(2) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 119.4(2) . . ? C14 C13 H13 120.3 . . ? C12 C13 H13 120.3 . . ? C13 C14 C15 120.6(2) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C16 120.8(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 H15 119.6 . . ? C15 C16 C11 118.6(2) . . ? C15 C16 N4 120.8(2) . . ? C11 C16 N4 120.50(18) . . ? N4 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N4 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N5 C19 C20 123.4(3) . . ? N5 C19 H19 118.3 . . ? C20 C19 H19 118.3 . . ? C21 C20 C19 118.3(3) . . ? C21 C20 H20 120.8 . . ? C19 C20 H20 120.8 . . ? C20 C21 C22 119.3(2) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C21 C22 C23 118.84(15) . . ? C21 C22 H22 120.6 . . ? C23 C22 H22 120.6 . . ? N5 C23 C22 122.66(13) . . ? N5 C23 H23 118.7 . . ? C22 C23 H23 118.7 . . ? N6 C24 C25 122.5(2) . . ? N6 C24 H24 118.8 . . ? C25 C24 H24 118.8 . . ? C26 C25 C24 119.2(2) . . ? C26 C25 H25 120.4 . . ? C24 C25 H25 120.4 . . ? C25 C26 C27 118.4(2) . . ? C25 C26 H26 120.8 . . ? C27 C26 H26 120.8 . . ? C28 C27 C26 119.4(2) . . ? C28 C27 H27 120.3 . . ? C26 C27 H27 120.3 . . ? N6 C28 C27 122.4(2) . . ? N6 C28 H28 118.8 . . ? C27 C28 H28 118.8 . . ? N7 C29 C30 123.5(2) . . ? N7 C29 H29 118.2 . . ? C30 C29 H29 118.2 . . ? C29 C30 C31 118.7(2) . . ? C29 C30 H30 120.7 . . ? C31 C30 H30 120.7 . . ? C30 C31 C32 118.7(2) . . ? C30 C31 H31 120.6 . . ? C32 C31 H31 120.6 . . ? C33 C32 C31 118.4(2) . . ? C33 C32 H32 120.8 . . ? C31 C32 H32 120.8 . . ? N7 C33 C32 123.6(2) . . ? N7 C33 H33 118.2 . . ? C32 C33 H33 118.2 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.596 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.065 _database_code_depnum_ccdc_archive 'CCDC 885551' ####################################################################### # # 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_cmd165b3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu5(L)4(4,4-bpy)3](ClO4)2.H2O' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C66 H64 Cl2 Cu5 N14 O17' _chemical_formula_weight 1713.91 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3776(7) _cell_length_b 12.6211(9) _cell_length_c 12.6793(8) _cell_angle_alpha 90.229(6) _cell_angle_beta 107.558(6) _cell_angle_gamma 104.589(6) _cell_volume 1673.60(19) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _exptl_crystal_description Parallelepiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.701 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 873 _exptl_absorpt_coefficient_mu 1.726 _cell_measurement_theta_max 25.35 _cell_measurement_theta_min 2.9328 _cell_measurement_reflns_used 5730 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_T_min 0.41537 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 12011 _diffrn_reflns_av_R_equivalents 0.0867 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.9328 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 -0.0335417000 _diffrn_orient_matrix_UB_12 -0.0557872000 _diffrn_orient_matrix_UB_13 -0.0010358000 _diffrn_orient_matrix_UB_21 -0.0171590000 _diffrn_orient_matrix_UB_22 0.0131984000 _diffrn_orient_matrix_UB_23 0.0467782000 _diffrn_orient_matrix_UB_31 -0.0563938000 _diffrn_orient_matrix_UB_32 0.0105561000 _diffrn_orient_matrix_UB_33 -0.0357709000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -73.00 -46.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -0.1953 -37.0000 -180.0000 36 #__ type_ start__ end____ width___ exp.time_ 2 omega -9.00 17.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -0.1953 -37.0000 -180.0000 35 #__ type_ start__ end____ width___ exp.time_ 3 omega -52.00 65.00 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 28.9080 -37.0000 150.0000 156 #__ type_ start__ end____ width___ exp.time_ 4 omega 70.00 110.50 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 28.9080 179.0000 -90.0000 54 #__ type_ start__ end____ width___ exp.time_ 5 omega -56.00 63.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 28.9080 -37.0000 -90.0000 159 #__ type_ start__ end____ width___ exp.time_ 6 omega -56.00 69.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 28.9080 -37.0000 30.0000 167 #__ type_ start__ end____ width___ exp.time_ 7 omega 71.00 112.25 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - 28.9080 179.0000 30.0000 55 #__ type_ start__ end____ width___ exp.time_ 8 omega -126.00 -64.50 0.7500 40.0000 omega____ theta____ kappa____ phi______ frames - -29.2986 179.0000 -90.0000 82 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150(2) _reflns_number_total 6117 _reflns_number_gt 4231 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.1282P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6117 _refine_ls_number_parameters 474 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0953 _refine_ls_R_factor_gt 0.0696 _refine_ls_wR_factor_ref 0.2254 _refine_ls_wR_factor_gt 0.1798 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 0.0000 0.0193(3) Uani 1 2 d S . . Cu2 Cu 0.01178(7) 0.23368(5) -0.10614(6) 0.0187(2) Uani 1 1 d . . . Cu3 Cu 0.06146(7) 0.12139(6) 0.24470(6) 0.0195(2) Uani 1 1 d . . . Cl1 Cl 0.6212(2) 0.30949(15) 0.26431(18) 0.0463(5) Uani 1 1 d . . . N1 N -0.0027(5) 0.1028(4) -0.1919(4) 0.0171(11) Uani 1 1 d . . . N2 N 0.0428(5) 0.3204(4) -0.2327(4) 0.0248(12) Uani 1 1 d . . . N3 N -0.2011(5) 0.2224(4) -0.1408(4) 0.0211(11) Uani 1 1 d . . . N4 N -0.7792(5) 0.0601(4) -0.0138(4) 0.0250(12) Uani 1 1 d . . . N5 N 0.0620(5) 0.2057(4) 0.1182(4) 0.0181(11) Uani 1 1 d . . . N6 N 0.0464(5) 0.2561(4) 0.3209(4) 0.0241(12) Uani 1 1 d . . . N7 N 0.2368(5) 0.1047(4) 0.3749(4) 0.0270(13) Uani 1 1 d . . . O1 O 0.0507(4) -0.0059(3) -0.3029(3) 0.0220(10) Uani 1 1 d . . . O2 O -0.0673(4) 0.0038(3) -0.1622(3) 0.0175(9) Uani 1 1 d . . . O3 O 0.0853(4) 0.3503(3) 0.0153(3) 0.0217(9) Uani 1 1 d . . . O4 O -0.0014(4) 0.1471(3) 0.0148(3) 0.0183(9) Uani 1 1 d . . . O5 O 0.7049(7) 0.3378(6) 0.3737(5) 0.085(2) Uani 1 1 d . . . O6 O 0.5950(7) 0.1947(4) 0.2379(6) 0.070(2) Uani 1 1 d . . . O7 O 0.6802(5) 0.3643(4) 0.1903(4) 0.0462(14) Uani 1 1 d . . . O8 O 0.5063(6) 0.3384(5) 0.2519(7) 0.082(2) Uani 1 1 d . . . O9 O 0.4574(9) 0.4906(7) 0.0330(7) 0.032(2) Uiso 0.50 1 d P . . C1 C 0.0572(6) 0.0889(5) -0.2612(5) 0.0212(13) Uani 1 1 d . . . C2 C 0.1472(6) 0.1865(5) -0.2817(5) 0.0216(14) Uani 1 1 d . . . C3 C 0.2439(6) 0.1660(5) -0.3162(5) 0.0230(14) Uani 1 1 d . . . H3 H 0.2430 0.0921 -0.3321 0.028 Uiso 1 1 calc R . . C4 C 0.3417(7) 0.2497(5) -0.3283(5) 0.0287(15) Uani 1 1 d . . . H4 H 0.4085 0.2339 -0.3506 0.034 Uiso 1 1 calc R . . C5 C 0.3416(7) 0.3550(5) -0.3081(6) 0.0311(16) Uani 1 1 d . . . H5 H 0.4082 0.4137 -0.3168 0.037 Uiso 1 1 calc R . . C6 C 0.2454(7) 0.3772(5) -0.2748(5) 0.0277(15) Uani 1 1 d . . . H6 H 0.2466 0.4514 -0.2602 0.033 Uiso 1 1 calc R . . C7 C 0.1484(6) 0.2948(5) -0.2624(5) 0.0211(13) Uani 1 1 d . . . C8 C -0.0747(7) 0.2917(6) -0.3317(5) 0.0335(17) Uani 1 1 d . . . H8A H -0.0576 0.3322 -0.3936 0.050 Uiso 1 1 calc R . . H8B H -0.1447 0.3115 -0.3135 0.050 Uiso 1 1 calc R . . H8C H -0.0990 0.2125 -0.3530 0.050 Uiso 1 1 calc R . . C9 C 0.0674(8) 0.4370(5) -0.1969(6) 0.0358(18) Uani 1 1 d . . . H9A H 0.1472 0.4598 -0.1349 0.054 Uiso 1 1 calc R . . H9B H -0.0034 0.4476 -0.1729 0.054 Uiso 1 1 calc R . . H9C H 0.0748 0.4815 -0.2589 0.054 Uiso 1 1 calc R . . C10 C 0.0992(6) 0.3092(5) 0.1097(5) 0.0199(13) Uani 1 1 d . . . C11 C 0.1642(6) 0.3798(5) 0.2133(5) 0.0224(14) Uani 1 1 d . . . C12 C 0.2470(6) 0.4758(5) 0.2093(6) 0.0280(15) Uani 1 1 d . . . H12 H 0.2584 0.4945 0.1398 0.034 Uiso 1 1 calc R . . C13 C 0.3157(7) 0.5477(5) 0.3015(6) 0.0322(16) Uani 1 1 d . . . H13 H 0.3754 0.6139 0.2966 0.039 Uiso 1 1 calc R . . C14 C 0.2961(7) 0.5218(5) 0.3996(6) 0.0376(18) Uani 1 1 d . . . H14 H 0.3431 0.5700 0.4646 0.045 Uiso 1 1 calc R . . C15 C 0.2097(7) 0.4273(5) 0.4056(5) 0.0302(16) Uani 1 1 d . . . H15 H 0.1957 0.4116 0.4747 0.036 Uiso 1 1 calc R . . C16 C 0.1428(6) 0.3547(5) 0.3147(5) 0.0218(14) Uani 1 1 d . . . C17 C -0.0817(6) 0.2674(5) 0.2669(5) 0.0293(15) Uani 1 1 d . . . H17A H -0.0958 0.3278 0.3060 0.044 Uiso 1 1 calc R . . H17B H -0.1448 0.1989 0.2687 0.044 Uiso 1 1 calc R . . H17C H -0.0909 0.2830 0.1896 0.044 Uiso 1 1 calc R . . C18 C 0.0516(7) 0.2316(5) 0.4362(5) 0.0324(17) Uani 1 1 d . . . H18A H 0.1380 0.2277 0.4780 0.049 Uiso 1 1 calc R . . H18B H -0.0098 0.1611 0.4350 0.049 Uiso 1 1 calc R . . H18C H 0.0300 0.2899 0.4718 0.049 Uiso 1 1 calc R . . C19 C -0.2290(6) 0.2829(5) -0.0690(5) 0.0246(14) Uani 1 1 d . . . H19 H -0.1669 0.3482 -0.0319 0.030 Uiso 1 1 calc R . . C20 C -0.3429(6) 0.2546(5) -0.0471(5) 0.0269(15) Uani 1 1 d . . . H20 H -0.3582 0.2994 0.0050 0.032 Uiso 1 1 calc R . . C21 C -0.4349(6) 0.1617(5) -0.1004(5) 0.0210(13) Uani 1 1 d . . . C22 C -0.5555(7) 0.1252(5) -0.0733(5) 0.0253(15) Uani 1 1 d . . . C23 C -0.5999(7) 0.1984(5) -0.0227(5) 0.0300(16) Uani 1 1 d . . . H23 H -0.5538 0.2737 -0.0077 0.036 Uiso 1 1 calc R . . C24 C -0.7084(7) 0.1626(5) 0.0052(5) 0.0305(16) Uani 1 1 d . . . H24 H -0.7351 0.2145 0.0405 0.037 Uiso 1 1 calc R . . C25 C -0.7389(6) -0.0096(5) -0.0644(5) 0.0256(14) Uani 1 1 d . . . H25 H -0.7880 -0.0842 -0.0792 0.031 Uiso 1 1 calc R . . C26 C -0.6325(6) 0.0189(5) -0.0962(5) 0.0251(14) Uani 1 1 d . . . H26 H -0.6108 -0.0345 -0.1344 0.030 Uiso 1 1 calc R . . C27 C -0.4075(6) 0.1008(5) -0.1769(5) 0.0267(15) Uani 1 1 d . . . H27 H -0.4693 0.0371 -0.2179 0.032 Uiso 1 1 calc R . . C28 C -0.2908(6) 0.1338(5) -0.1923(5) 0.0264(15) Uani 1 1 d . . . H28 H -0.2728 0.0901 -0.2435 0.032 Uiso 1 1 calc R . . C29 C 0.2279(7) 0.0236(5) 0.4406(5) 0.0263(14) Uani 1 1 d . . . H29 H 0.1486 -0.0062 0.4536 0.032 Uiso 1 1 calc R . . C30 C 0.3288(7) -0.0192(5) 0.4906(5) 0.0285(15) Uani 1 1 d . . . H30 H 0.3175 -0.0782 0.5360 0.034 Uiso 1 1 calc R . . C31 C 0.4462(6) 0.0226(5) 0.4756(5) 0.0245(14) Uani 1 1 d . . . C32 C 0.4559(7) 0.1085(6) 0.4126(7) 0.044(2) Uani 1 1 d . . . H32 H 0.5358 0.1429 0.4025 0.053 Uiso 1 1 calc R . . C33 C 0.3487(7) 0.1470(6) 0.3620(6) 0.0397(19) Uani 1 1 d . . . H33 H 0.3575 0.2062 0.3165 0.048 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 0.0333(7) 0.0121(5) 0.0152(6) -0.0032(4) 0.0109(5) 0.0071(4) Cu2 0.0304(5) 0.0136(4) 0.0170(4) -0.0012(3) 0.0131(4) 0.0076(3) Cu3 0.0332(5) 0.0147(4) 0.0150(4) -0.0027(3) 0.0110(4) 0.0097(3) Cl1 0.0568(13) 0.0346(10) 0.0573(13) -0.0123(9) 0.0383(11) 0.0047(9) N1 0.025(3) 0.012(2) 0.014(2) 0.0002(19) 0.007(2) 0.004(2) N2 0.040(4) 0.014(3) 0.030(3) 0.002(2) 0.024(3) 0.009(2) N3 0.015(3) 0.029(3) 0.025(3) 0.002(2) 0.009(2) 0.011(2) N4 0.032(3) 0.028(3) 0.016(3) 0.000(2) 0.008(2) 0.010(2) N5 0.022(3) 0.017(3) 0.017(3) -0.008(2) 0.007(2) 0.005(2) N6 0.038(3) 0.018(3) 0.017(3) -0.004(2) 0.011(2) 0.006(2) N7 0.036(3) 0.024(3) 0.020(3) -0.004(2) 0.007(3) 0.008(2) O1 0.033(3) 0.017(2) 0.022(2) -0.0034(17) 0.014(2) 0.0099(18) O2 0.022(2) 0.014(2) 0.017(2) -0.0027(16) 0.0111(18) 0.0014(17) O3 0.031(3) 0.017(2) 0.020(2) -0.0024(17) 0.012(2) 0.0080(18) O4 0.028(2) 0.014(2) 0.014(2) -0.0084(16) 0.0104(19) 0.0030(17) O5 0.095(6) 0.114(6) 0.049(4) -0.025(4) 0.036(4) 0.018(5) O6 0.106(6) 0.029(3) 0.100(5) -0.005(3) 0.069(5) 0.016(3) O7 0.054(4) 0.040(3) 0.047(3) -0.014(2) 0.030(3) 0.001(3) O8 0.062(4) 0.056(4) 0.156(7) 0.001(4) 0.072(5) 0.019(3) C1 0.034(4) 0.018(3) 0.015(3) 0.000(2) 0.010(3) 0.010(3) C2 0.034(4) 0.017(3) 0.016(3) 0.000(2) 0.013(3) 0.005(3) C3 0.039(4) 0.020(3) 0.013(3) -0.004(2) 0.009(3) 0.011(3) C4 0.034(4) 0.036(4) 0.021(3) 0.002(3) 0.015(3) 0.010(3) C5 0.038(4) 0.024(4) 0.033(4) -0.001(3) 0.021(3) -0.002(3) C6 0.038(4) 0.019(3) 0.032(4) -0.001(3) 0.018(3) 0.010(3) C7 0.030(4) 0.018(3) 0.020(3) -0.002(2) 0.010(3) 0.010(3) C8 0.052(5) 0.033(4) 0.028(4) 0.013(3) 0.022(4) 0.021(3) C9 0.062(5) 0.016(3) 0.046(4) 0.002(3) 0.039(4) 0.012(3) C10 0.027(4) 0.018(3) 0.021(3) -0.004(2) 0.012(3) 0.012(3) C11 0.026(4) 0.018(3) 0.027(3) -0.004(3) 0.008(3) 0.014(3) C12 0.033(4) 0.024(3) 0.033(4) -0.004(3) 0.014(3) 0.012(3) C13 0.036(4) 0.023(4) 0.038(4) -0.010(3) 0.010(3) 0.010(3) C14 0.049(5) 0.025(4) 0.033(4) -0.018(3) 0.008(4) 0.007(3) C15 0.034(4) 0.033(4) 0.024(4) -0.008(3) 0.006(3) 0.013(3) C16 0.027(4) 0.022(3) 0.022(3) -0.006(2) 0.009(3) 0.014(3) C17 0.035(4) 0.028(4) 0.035(4) 0.000(3) 0.017(3) 0.019(3) C18 0.057(5) 0.025(4) 0.025(4) 0.000(3) 0.022(4) 0.016(3) C19 0.019(3) 0.028(3) 0.031(4) -0.003(3) 0.011(3) 0.010(3) C20 0.033(4) 0.027(4) 0.026(4) -0.005(3) 0.013(3) 0.012(3) C21 0.018(3) 0.022(3) 0.025(3) -0.003(3) 0.007(3) 0.009(3) C22 0.038(4) 0.024(3) 0.018(3) 0.003(3) 0.012(3) 0.012(3) C23 0.038(4) 0.019(3) 0.033(4) -0.010(3) 0.016(3) 0.003(3) C24 0.040(4) 0.024(4) 0.029(4) -0.011(3) 0.016(3) 0.006(3) C25 0.032(4) 0.021(3) 0.023(3) -0.003(3) 0.008(3) 0.007(3) C26 0.038(4) 0.023(3) 0.019(3) -0.003(3) 0.013(3) 0.012(3) C27 0.029(4) 0.029(4) 0.022(3) -0.008(3) 0.008(3) 0.007(3) C28 0.031(4) 0.028(4) 0.027(4) -0.005(3) 0.014(3) 0.013(3) C29 0.029(4) 0.029(4) 0.021(3) -0.005(3) 0.008(3) 0.007(3) C30 0.039(4) 0.027(4) 0.022(3) 0.005(3) 0.007(3) 0.015(3) C31 0.025(4) 0.029(3) 0.023(3) 0.000(3) 0.007(3) 0.013(3) C32 0.035(4) 0.048(5) 0.058(5) 0.032(4) 0.023(4) 0.014(4) C33 0.031(4) 0.042(4) 0.046(5) 0.019(4) 0.011(4) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O4 1.870(4) 2 ? Cu1 O4 1.870(4) . ? Cu1 O2 1.971(4) 2 ? Cu1 O2 1.971(4) . ? Cu2 O4 1.908(4) . ? Cu2 N1 1.919(5) . ? Cu2 O3 1.955(4) . ? Cu2 N2 2.014(5) . ? Cu2 N3 2.294(5) . ? Cu3 O2 1.917(4) 2 ? Cu3 N5 1.929(5) . ? Cu3 O1 1.984(4) 2 ? Cu3 N6 2.021(5) . ? Cu3 N7 2.232(5) . ? Cl1 O7 1.400(5) . ? Cl1 O8 1.409(6) . ? Cl1 O5 1.409(7) . ? Cl1 O6 1.420(6) . ? N1 C1 1.298(7) . ? N1 O2 1.397(6) . ? N2 C7 1.469(7) . ? N2 C9 1.471(8) . ? N2 C8 1.495(9) . ? N3 C28 1.317(8) . ? N3 C19 1.342(8) . ? N4 C24 1.318(8) . ? N4 C25 1.332(8) . ? N5 C10 1.284(7) . ? N5 O4 1.393(6) . ? N6 C17 1.454(8) . ? N6 C16 1.457(8) . ? N6 C18 1.483(8) . ? N7 C33 1.310(9) . ? N7 C29 1.325(8) . ? O1 C1 1.282(7) . ? O1 Cu3 1.984(4) 2 ? O2 Cu3 1.917(4) 2 ? O3 C10 1.287(7) . ? O9 O9 1.440(17) 2_665 ? C1 C2 1.470(8) . ? C2 C3 1.379(8) . ? C2 C7 1.383(8) . ? C3 C4 1.375(9) . ? C3 H3 0.9500 . ? C4 C5 1.353(9) . ? C4 H4 0.9500 . ? C5 C6 1.373(9) . ? C5 H5 0.9500 . ? C6 C7 1.361(9) . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.463(8) . ? C11 C12 1.346(9) . ? C11 C16 1.402(8) . ? C12 C13 1.372(9) . ? C12 H12 0.9500 . ? C13 C14 1.356(10) . ? C13 H13 0.9500 . ? C14 C15 1.359(10) . ? C14 H14 0.9500 . ? C15 C16 1.364(9) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.367(9) . ? C19 H19 0.9500 . ? C20 C21 1.369(9) . ? C20 H20 0.9500 . ? C21 C27 1.387(8) . ? C21 C22 1.477(9) . ? C22 C26 1.380(9) . ? C22 C23 1.394(8) . ? C23 C24 1.355(9) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C26 1.353(9) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.362(9) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? C29 C30 1.374(9) . ? C29 H29 0.9500 . ? C30 C31 1.378(9) . ? C30 H30 0.9500 . ? C31 C32 1.351(9) . ? C31 C31 1.449(12) 2_656 ? C32 C33 1.402(10) . ? C32 H32 0.9500 . ? C33 H33 0.9500 . ? 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 O4 180.0(3) 2 . ? O4 Cu1 O2 88.11(16) 2 2 ? O4 Cu1 O2 91.89(16) . 2 ? O4 Cu1 O2 91.89(16) 2 . ? O4 Cu1 O2 88.11(16) . . ? O2 Cu1 O2 180.00(9) 2 . ? O4 Cu2 N1 88.65(17) . . ? O4 Cu2 O3 80.83(16) . . ? N1 Cu2 O3 157.58(19) . . ? O4 Cu2 N2 173.91(19) . . ? N1 Cu2 N2 88.48(19) . . ? O3 Cu2 N2 99.99(18) . . ? O4 Cu2 N3 86.40(17) . . ? N1 Cu2 N3 99.5(2) . . ? O3 Cu2 N3 99.58(18) . . ? N2 Cu2 N3 99.4(2) . . ? O2 Cu3 N5 89.85(17) 2 . ? O2 Cu3 O1 81.77(16) 2 2 ? N5 Cu3 O1 142.3(2) . 2 ? O2 Cu3 N6 175.62(19) 2 . ? N5 Cu3 N6 86.68(19) . . ? O1 Cu3 N6 99.37(18) 2 . ? O2 Cu3 N7 88.10(18) 2 . ? N5 Cu3 N7 124.6(2) . . ? O1 Cu3 N7 92.00(18) 2 . ? N6 Cu3 N7 96.1(2) . . ? O7 Cl1 O8 109.2(4) . . ? O7 Cl1 O5 109.4(4) . . ? O8 Cl1 O5 111.0(5) . . ? O7 Cl1 O6 108.0(3) . . ? O8 Cl1 O6 109.9(4) . . ? O5 Cl1 O6 109.3(5) . . ? C1 N1 O2 113.0(5) . . ? C1 N1 Cu2 129.4(4) . . ? O2 N1 Cu2 116.4(3) . . ? C7 N2 C9 113.6(5) . . ? C7 N2 C8 109.0(5) . . ? C9 N2 C8 107.4(5) . . ? C7 N2 Cu2 109.6(4) . . ? C9 N2 Cu2 107.0(4) . . ? C8 N2 Cu2 110.1(4) . . ? C28 N3 C19 116.7(5) . . ? C28 N3 Cu2 121.6(4) . . ? C19 N3 Cu2 115.8(4) . . ? C24 N4 C25 115.9(6) . . ? C10 N5 O4 111.7(5) . . ? C10 N5 Cu3 132.3(4) . . ? O4 N5 Cu3 115.6(3) . . ? C17 N6 C16 110.9(5) . . ? C17 N6 C18 106.0(5) . . ? C16 N6 C18 113.4(5) . . ? C17 N6 Cu3 106.9(4) . . ? C16 N6 Cu3 112.1(4) . . ? C18 N6 Cu3 107.2(4) . . ? C33 N7 C29 117.4(6) . . ? C33 N7 Cu3 119.0(4) . . ? C29 N7 Cu3 119.4(4) . . ? C1 O1 Cu3 109.6(4) . 2 ? N1 O2 Cu3 112.3(3) . 2 ? N1 O2 Cu1 108.7(3) . . ? Cu3 O2 Cu1 113.49(19) 2 . ? C10 O3 Cu2 110.5(4) . . ? N5 O4 Cu1 118.2(3) . . ? N5 O4 Cu2 113.2(3) . . ? Cu1 O4 Cu2 117.86(19) . . ? O1 C1 N1 123.1(5) . . ? O1 C1 C2 119.3(5) . . ? N1 C1 C2 117.3(5) . . ? C3 C2 C7 118.2(6) . . ? C3 C2 C1 115.4(5) . . ? C7 C2 C1 126.2(6) . . ? C4 C3 C2 121.7(6) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C5 C4 C3 119.1(6) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 120.1(6) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C7 C6 C5 121.2(6) . . ? C7 C6 H6 119.4 . . ? C5 C6 H6 119.4 . . ? C6 C7 C2 119.7(6) . . ? C6 C7 N2 120.3(5) . . ? C2 C7 N2 120.0(5) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N5 C10 O3 122.7(5) . . ? N5 C10 C11 116.8(5) . . ? O3 C10 C11 120.5(5) . . ? C12 C11 C16 118.7(6) . . ? C12 C11 C10 117.3(6) . . ? C16 C11 C10 124.0(6) . . ? C11 C12 C13 122.7(7) . . ? C11 C12 H12 118.7 . . ? C13 C12 H12 118.7 . . ? C14 C13 C12 118.2(7) . . ? C14 C13 H13 120.9 . . ? C12 C13 H13 120.9 . . ? C15 C14 C13 120.5(7) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 121.5(6) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C15 C16 C11 118.4(6) . . ? C15 C16 N6 121.1(6) . . ? C11 C16 N6 120.5(5) . . ? N6 C17 H17A 109.5 . . ? N6 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N6 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N6 C18 H18A 109.5 . . ? N6 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N6 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N3 C19 C20 122.8(6) . . ? N3 C19 H19 118.6 . . ? C20 C19 H19 118.6 . . ? C19 C20 C21 120.0(6) . . ? C19 C20 H20 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 C27 117.2(6) . . ? C20 C21 C22 121.2(5) . . ? C27 C21 C22 121.5(6) . . ? C26 C22 C23 115.3(6) . . ? C26 C22 C21 123.6(6) . . ? C23 C22 C21 121.2(6) . . ? C24 C23 C22 120.3(6) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? N4 C24 C23 124.0(6) . . ? N4 C24 H24 118.0 . . ? C23 C24 H24 118.0 . . ? N4 C25 C26 124.2(6) . . ? N4 C25 H25 117.9 . . ? C26 C25 H25 117.9 . . ? C25 C26 C22 120.2(6) . . ? C25 C26 H26 119.9 . . ? C22 C26 H26 119.9 . . ? C28 C27 C21 119.0(6) . . ? C28 C27 H27 120.5 . . ? C21 C27 H27 120.5 . . ? N3 C28 C27 124.3(6) . . ? N3 C28 H28 117.9 . . ? C27 C28 H28 117.9 . . ? N7 C29 C30 122.6(6) . . ? N7 C29 H29 118.7 . . ? C30 C29 H29 118.7 . . ? C29 C30 C31 120.7(6) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? C32 C31 C30 116.2(6) . . ? C32 C31 C31 121.6(8) . 2_656 ? C30 C31 C31 122.2(7) . 2_656 ? C31 C32 C33 120.3(7) . . ? C31 C32 H32 119.8 . . ? C33 C32 H32 119.8 . . ? N7 C33 C32 122.7(7) . . ? N7 C33 H33 118.7 . . ? C32 C33 H33 118.7 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.879 _refine_diff_density_min -2.267 _refine_diff_density_rms 0.205 _database_code_depnum_ccdc_archive 'CCDC 885552' ####################################################################### # # 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_cmd216a3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu5]-tzp' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C48 H56 Cl2 Cu5 N12 O18' _chemical_formula_weight 1477.65 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _space_group_name_Hall '-P 2yn' 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 12.6809(3) _cell_length_b 10.7919(3) _cell_length_c 20.7122(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.018(2) _cell_angle_gamma 90.00 _cell_volume 2791.27(12) _cell_formula_units_Z 2 _cell_measurement_temperature 149.8 _cell_measurement_reflns_used 6236 _cell_measurement_theta_min 2.9901 _cell_measurement_theta_max 25.35 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.758 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1502 _exptl_absorpt_coefficient_mu 2.054 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.81554 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 23235 _diffrn_reflns_av_R_equivalents 0.0547 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 0.0100310000 _diffrn_orient_matrix_UB_12 0.0074661000 _diffrn_orient_matrix_UB_21 0.0298382000 _diffrn_orient_matrix_UB_22 -0.0559220000 _diffrn_orient_matrix_UB_23 0.0030401000 _diffrn_orient_matrix_UB_31 -0.0472843000 _diffrn_orient_matrix_UB_32 -0.0337119000 _diffrn_orient_matrix_UB_33 -0.0122175000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -28.00 19.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -14.2653 -96.0000 -59.0000 47 #__ type_ start__ end____ width___ exp.time_ 2 omega -85.00 -37.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - -14.2653 179.0000 150.0000 48 #__ type_ start__ end____ width___ exp.time_ 3 omega 16.00 77.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 77.0000 -180.0000 61 #__ type_ start__ end____ width___ exp.time_ 4 omega 7.00 58.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 -96.0000 119.0000 51 #__ type_ start__ end____ width___ exp.time_ 5 omega -3.00 95.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 37.0000 90.0000 98 #__ type_ start__ end____ width___ exp.time_ 6 omega -42.00 49.00 1.0000 30.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 -37.0000 -90.0000 91 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 149.8 _reflns_number_total 5090 _reflns_number_gt 3963 _reflns_threshold_expression >2sigma(I) _computing_structure_solution SHELXS97 _computing_structure_refinement 'SHELXL-97/2 (Sheldrick,1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0362P)^2^+2.5861P] 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 5090 _refine_ls_number_parameters 390 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0874 _refine_ls_wR_factor_gt 0.0798 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.5000 0.0000 0.0000 0.01322(15) Uani 1 2 d S . . Cl1 Cl 0.45494(7) 0.82081(10) 0.15074(5) 0.0277(2) Uani 1 1 d . . . O1 O 0.80788(18) -0.1752(2) -0.00386(12) 0.0195(6) Uani 1 1 d . . . N1 N 0.7247(2) -0.0274(3) 0.04820(14) 0.0147(7) Uani 1 1 d . . . C1 C 0.8079(3) -0.0955(4) 0.04277(17) 0.0148(8) Uani 1 1 d . . . Cu2 Cu 0.69095(3) 0.07661(4) 0.11871(2) 0.01285(12) Uani 1 1 d . . . O2 O 0.64096(17) -0.0488(2) -0.00431(11) 0.0169(6) Uani 1 1 d . . . N2 N 0.8138(2) -0.0121(3) 0.18172(14) 0.0188(7) Uani 1 1 d . . . C2 C 0.9078(3) -0.0698(3) 0.09001(17) 0.0156(8) Uani 1 1 d . . . Cu3 Cu 0.33418(3) 0.18411(4) 0.05777(2) 0.01557(12) Uani 1 1 d . . . O3 O 0.61978(17) 0.1440(2) 0.18632(11) 0.0159(6) Uani 1 1 d . . . N3 N 0.4813(2) 0.1672(3) 0.10103(14) 0.0138(7) Uani 1 1 d . . . C3 C 1.0030(3) -0.0873(4) 0.06588(18) 0.0225(9) Uani 1 1 d . . . H3 H 1.0008 -0.1238 0.0239 0.027 Uiso 1 1 calc R . . O4 O 0.55629(17) 0.1280(2) 0.06237(11) 0.0142(5) Uani 1 1 d . . . N4 N 0.3078(2) 0.3038(3) 0.12815(15) 0.0202(7) Uani 1 1 d . . . C4 C 1.1005(3) -0.0523(4) 0.10228(19) 0.0233(9) Uani 1 1 d . . . H4 H 1.1648 -0.0646 0.0854 0.028 Uiso 1 1 calc R . . O5 O 0.5271(2) 0.8621(3) 0.10866(14) 0.0331(7) Uani 1 1 d . . . N5 N 0.7845(2) 0.2420(3) 0.09029(14) 0.0188(7) Uani 1 1 d . . . C5 C 1.1036(3) 0.0003(4) 0.1629(2) 0.0248(9) Uani 1 1 d . . . H5 H 1.1701 0.0271 0.1873 0.030 Uiso 1 1 calc R . . O6 O 0.4261(4) 0.6988(4) 0.1357(3) 0.112(2) Uani 1 1 d . . . N6 N 1.0050(4) 0.5052(4) 0.02698(17) 0.0548(13) Uani 1 1 d . . . C6 C 1.0109(3) 0.0147(4) 0.18887(18) 0.0224(9) Uani 1 1 d . . . H6 H 1.0146 0.0495 0.2313 0.027 Uiso 1 1 calc R . . O7 O 0.5068(3) 0.8284(5) 0.21644(17) 0.0874(17) Uani 1 1 d . . . C7 C 0.9120(3) -0.0216(4) 0.15316(18) 0.0174(8) Uani 1 1 d . . . O8 O 0.3632(2) 0.8973(4) 0.14326(18) 0.0567(11) Uani 1 1 d . . . C8 C 0.7726(3) -0.1398(4) 0.1921(2) 0.0293(10) Uani 1 1 d . . . H8A H 0.7614 -0.1851 0.1504 0.044 Uiso 1 1 calc R . . H8B H 0.7046 -0.1335 0.2082 0.044 Uiso 1 1 calc R . . H8C H 0.8250 -0.1840 0.2243 0.044 Uiso 1 1 calc R . . O9 O 0.3976(3) 0.3264(3) -0.02096(15) 0.0432(9) Uani 1 1 d . . . H9 H 0.4723 0.3189 -0.0207 0.052 Uiso 1 1 calc R . . C9 C 0.8304(3) 0.0484(5) 0.24732(19) 0.0347(11) Uani 1 1 d . . . H9A H 0.8810 -0.0006 0.2783 0.052 Uiso 1 1 calc R . . H9B H 0.7618 0.0537 0.2629 0.052 Uiso 1 1 calc R . . H9C H 0.8592 0.1320 0.2439 0.052 Uiso 1 1 calc R . . C10 C 0.5209(3) 0.1699(3) 0.16311(17) 0.0132(8) Uani 1 1 d . . . C11 C 0.4462(3) 0.1953(3) 0.20953(17) 0.0152(8) Uani 1 1 d . . . C12 C 0.4797(3) 0.1548(4) 0.27382(17) 0.0196(9) Uani 1 1 d . . . H12 H 0.5499 0.1222 0.2861 0.024 Uiso 1 1 calc R . . C13 C 0.4136(3) 0.1607(4) 0.31987(18) 0.0238(9) Uani 1 1 d . . . H13 H 0.4384 0.1327 0.3633 0.029 Uiso 1 1 calc R . . C14 C 0.3120(3) 0.2072(4) 0.30290(19) 0.0247(9) Uani 1 1 d . . . H14 H 0.2654 0.2080 0.3341 0.030 Uiso 1 1 calc R . . C15 C 0.2771(3) 0.2529(4) 0.24030(19) 0.0236(9) Uani 1 1 d . . . H15 H 0.2073 0.2872 0.2294 0.028 Uiso 1 1 calc R . . C16 C 0.3432(3) 0.2490(3) 0.19336(17) 0.0163(8) Uani 1 1 d . . . C17 C 0.3700(3) 0.4212(4) 0.1236(2) 0.0298(10) Uani 1 1 d . . . H17A H 0.3574 0.4787 0.1581 0.045 Uiso 1 1 calc R . . H17B H 0.3467 0.4596 0.0806 0.045 Uiso 1 1 calc R . . H17C H 0.4466 0.4019 0.1292 0.045 Uiso 1 1 calc R . . C18 C 0.1925(3) 0.3369(4) 0.1155(2) 0.0347(11) Uani 1 1 d . . . H18A H 0.1499 0.2644 0.1233 0.052 Uiso 1 1 calc R . . H18B H 0.1717 0.3639 0.0699 0.052 Uiso 1 1 calc R . . H18C H 0.1797 0.4042 0.1450 0.052 Uiso 1 1 calc R . . C19 C 0.7757(3) 0.2614(4) 0.02594(19) 0.0283(10) Uani 1 1 d . . . H19 H 0.7223 0.2175 -0.0031 0.034 Uiso 1 1 calc R . . C20 C 0.8416(4) 0.3431(4) -0.0002(2) 0.0402(13) Uani 1 1 d . . . H20 H 0.8345 0.3536 -0.0463 0.048 Uiso 1 1 calc R . . C21 C 0.9176(3) 0.4088(4) 0.0418(3) 0.0373(12) Uani 1 1 d . . . C22 C 0.9245(3) 0.3918(4) 0.1075(2) 0.0373(11) Uani 1 1 d . . . H22 H 0.9752 0.4370 0.1377 0.045 Uiso 1 1 calc R . . C23 C 0.8572(3) 0.3084(4) 0.1296(2) 0.0286(10) Uani 1 1 d . . . H23 H 0.8628 0.2975 0.1756 0.034 Uiso 1 1 calc R . . C24 C 0.3503(6) 0.4137(6) -0.0650(3) 0.088(2) Uani 1 1 d . . . H24A H 0.3615 0.3914 -0.1091 0.131 Uiso 1 1 calc R . . H24B H 0.3824 0.4950 -0.0531 0.131 Uiso 1 1 calc R . . H24C H 0.2734 0.4171 -0.0640 0.131 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 0.0093(3) 0.0161(4) 0.0134(3) -0.0032(3) -0.0006(2) 0.0007(3) Cl1 0.0239(5) 0.0286(6) 0.0324(6) 0.0075(5) 0.0097(4) -0.0035(4) O1 0.0134(12) 0.0261(16) 0.0177(14) -0.0045(12) -0.0012(10) 0.0042(11) N1 0.0102(14) 0.0185(18) 0.0129(16) 0.0003(13) -0.0047(12) -0.0018(13) C1 0.0136(17) 0.018(2) 0.0133(19) 0.0018(15) 0.0034(14) -0.0002(16) Cu2 0.0105(2) 0.0166(3) 0.0107(2) -0.00063(18) -0.00007(16) -0.00002(18) O2 0.0115(12) 0.0238(16) 0.0132(13) -0.0088(11) -0.0040(10) 0.0013(11) N2 0.0148(15) 0.028(2) 0.0131(16) 0.0005(14) 0.0010(13) 0.0013(14) C2 0.0135(17) 0.013(2) 0.019(2) 0.0049(16) 0.0005(15) 0.0010(15) Cu3 0.0127(2) 0.0187(3) 0.0142(2) -0.00420(19) -0.00106(17) 0.00295(19) O3 0.0134(12) 0.0222(15) 0.0117(13) -0.0018(11) 0.0012(10) -0.0003(11) N3 0.0138(14) 0.0148(17) 0.0141(16) -0.0035(13) 0.0055(12) 0.0002(13) C3 0.0191(19) 0.031(3) 0.018(2) 0.0054(18) 0.0023(16) 0.0045(18) O4 0.0111(11) 0.0185(14) 0.0130(13) -0.0032(11) 0.0026(10) 0.0009(11) N4 0.0175(16) 0.0214(19) 0.0199(17) -0.0045(14) -0.0015(13) 0.0061(14) C4 0.0113(18) 0.029(2) 0.030(2) 0.0060(19) 0.0030(16) 0.0031(17) O5 0.0263(15) 0.042(2) 0.0332(17) 0.0122(14) 0.0117(13) -0.0019(14) N5 0.0204(16) 0.0167(18) 0.0192(17) 0.0011(14) 0.0032(13) -0.0035(14) C5 0.0139(18) 0.025(2) 0.033(2) 0.0064(19) -0.0043(17) -0.0042(17) O6 0.117(4) 0.042(3) 0.208(6) -0.042(3) 0.111(4) -0.043(3) N6 0.075(3) 0.047(3) 0.032(2) -0.013(2) -0.021(2) 0.034(2) C6 0.023(2) 0.025(2) 0.018(2) 0.0000(17) -0.0032(16) 0.0004(18) O7 0.048(2) 0.183(5) 0.031(2) 0.033(3) 0.0072(18) 0.020(3) C7 0.0148(18) 0.018(2) 0.018(2) 0.0026(16) 0.0006(15) 0.0008(16) O8 0.0271(17) 0.066(3) 0.081(3) 0.034(2) 0.0197(17) 0.0154(17) C8 0.023(2) 0.034(3) 0.030(2) 0.013(2) 0.0038(18) 0.004(2) O9 0.060(2) 0.036(2) 0.040(2) 0.0144(16) 0.0235(17) 0.0139(17) C9 0.031(2) 0.054(3) 0.018(2) -0.003(2) 0.0002(18) 0.011(2) C10 0.0147(17) 0.0087(19) 0.0157(19) -0.0012(15) 0.0014(15) -0.0033(15) C11 0.0175(18) 0.011(2) 0.0172(19) -0.0030(15) 0.0040(15) -0.0033(15) C12 0.0217(19) 0.022(2) 0.016(2) 0.0024(16) 0.0040(16) 0.0050(17) C13 0.037(2) 0.023(2) 0.013(2) 0.0028(16) 0.0108(17) 0.0030(19) C14 0.027(2) 0.023(2) 0.027(2) -0.0024(18) 0.0140(18) 0.0037(18) C15 0.0206(19) 0.023(2) 0.028(2) -0.0086(18) 0.0068(17) 0.0043(18) C16 0.0156(17) 0.011(2) 0.021(2) -0.0039(16) -0.0001(15) -0.0004(15) C17 0.045(3) 0.018(2) 0.023(2) 0.0005(18) -0.0016(19) 0.005(2) C18 0.030(2) 0.043(3) 0.028(2) -0.011(2) -0.0027(19) 0.019(2) C19 0.037(2) 0.026(3) 0.022(2) 0.0015(19) 0.0061(18) -0.002(2) C20 0.065(3) 0.032(3) 0.033(3) 0.015(2) 0.034(3) 0.013(3) C21 0.021(2) 0.016(2) 0.082(4) 0.014(2) 0.031(2) -0.0004(19) C22 0.026(2) 0.028(3) 0.057(3) 0.006(2) 0.005(2) -0.009(2) C23 0.027(2) 0.030(3) 0.028(2) -0.0021(19) 0.0040(18) -0.0068(19) C24 0.148(7) 0.065(5) 0.058(4) 0.028(4) 0.042(4) 0.043(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O2 1.880(2) 3_655 ? Cu1 O2 1.880(2) . ? Cu1 O4 1.940(2) . ? Cu1 O4 1.940(2) 3_655 ? Cl1 O6 1.387(4) . ? Cl1 O7 1.407(4) . ? Cl1 O8 1.413(3) . ? Cl1 O5 1.439(3) . ? O1 C1 1.293(4) . ? O1 Cu3 1.950(2) 3_655 ? N1 C1 1.307(4) . ? N1 O2 1.401(3) . ? N1 Cu2 1.947(3) . ? C1 C2 1.486(5) . ? Cu2 O3 1.935(2) . ? Cu2 O4 1.973(2) . ? Cu2 N2 2.083(3) . ? Cu2 N5 2.277(3) . ? O2 Cu3 1.892(2) 3_655 ? N2 C7 1.472(4) . ? N2 C9 1.489(5) . ? N2 C8 1.502(5) . ? C2 C3 1.397(5) . ? C2 C7 1.400(5) . ? Cu3 O2 1.892(2) 3_655 ? Cu3 N3 1.933(3) . ? Cu3 O1 1.950(2) 3_655 ? Cu3 N4 2.019(3) . ? Cu3 O9 2.474(3) . ? O3 C10 1.293(4) . ? N3 C10 1.297(4) . ? N3 O4 1.410(3) . ? C3 C4 1.384(5) . ? C3 H3 0.9500 . ? N4 C16 1.471(5) . ? N4 C18 1.483(5) . ? N4 C17 1.504(5) . ? C4 C5 1.373(6) . ? C4 H4 0.9500 . ? N5 C23 1.328(5) . ? N5 C19 1.335(5) . ? C5 C6 1.383(5) . ? C5 H5 0.9500 . ? N6 N6 1.108(7) 3_765 ? N6 C21 1.588(6) . ? C6 C7 1.397(5) . ? C6 H6 0.9500 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O9 C24 1.374(6) . ? O9 H9 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.487(5) . ? C11 C12 1.395(5) . ? C11 C16 1.415(5) . ? C12 C13 1.376(5) . ? C12 H12 0.9500 . ? C13 C14 1.370(5) . ? C13 H13 0.9500 . ? C14 C15 1.386(5) . ? C14 H14 0.9500 . ? C15 C16 1.390(5) . ? C15 H15 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.388(6) . ? C19 H19 0.9500 . ? C20 C21 1.376(7) . ? C20 H20 0.9500 . ? C21 C22 1.361(7) . ? C22 C23 1.372(6) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.0 3_655 . ? O2 Cu1 O4 90.68(10) 3_655 . ? O2 Cu1 O4 89.33(10) . . ? O2 Cu1 O4 89.33(10) 3_655 3_655 ? O2 Cu1 O4 90.67(10) . 3_655 ? O4 Cu1 O4 180.00(11) . 3_655 ? O6 Cl1 O7 109.5(4) . . ? O6 Cl1 O8 110.5(3) . . ? O7 Cl1 O8 108.0(3) . . ? O6 Cl1 O5 109.2(2) . . ? O7 Cl1 O5 109.2(2) . . ? O8 Cl1 O5 110.52(19) . . ? C1 O1 Cu3 109.9(2) . 3_655 ? C1 N1 O2 110.8(3) . . ? C1 N1 Cu2 132.4(2) . . ? O2 N1 Cu2 116.22(19) . . ? O1 C1 N1 122.9(3) . . ? O1 C1 C2 120.3(3) . . ? N1 C1 C2 116.6(3) . . ? O3 Cu2 N1 161.84(11) . . ? O3 Cu2 O4 81.82(9) . . ? N1 Cu2 O4 89.93(10) . . ? O3 Cu2 N2 96.39(11) . . ? N1 Cu2 N2 88.12(12) . . ? O4 Cu2 N2 167.37(11) . . ? O3 Cu2 N5 102.83(11) . . ? N1 Cu2 N5 93.77(12) . . ? O4 Cu2 N5 93.61(10) . . ? N2 Cu2 N5 98.97(11) . . ? N1 O2 Cu1 121.02(19) . . ? N1 O2 Cu3 113.64(19) . 3_655 ? Cu1 O2 Cu3 120.02(12) . 3_655 ? C7 N2 C9 113.7(3) . . ? C7 N2 C8 109.4(3) . . ? C9 N2 C8 105.6(3) . . ? C7 N2 Cu2 111.9(2) . . ? C9 N2 Cu2 110.0(2) . . ? C8 N2 Cu2 105.7(2) . . ? C3 C2 C7 119.3(3) . . ? C3 C2 C1 115.5(3) . . ? C7 C2 C1 125.0(3) . . ? O2 Cu3 N3 87.28(11) 3_655 . ? O2 Cu3 O1 81.85(10) 3_655 3_655 ? N3 Cu3 O1 169.13(11) . 3_655 ? O2 Cu3 N4 169.09(12) 3_655 . ? N3 Cu3 N4 89.65(12) . . ? O1 Cu3 N4 101.09(11) 3_655 . ? O2 Cu3 O9 89.26(11) 3_655 . ? N3 Cu3 O9 88.05(12) . . ? O1 Cu3 O9 91.55(11) 3_655 . ? N4 Cu3 O9 101.10(12) . . ? C10 O3 Cu2 110.9(2) . . ? C10 N3 O4 112.8(3) . . ? C10 N3 Cu3 129.3(2) . . ? O4 N3 Cu3 117.19(19) . . ? C4 C3 C2 120.9(4) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? N3 O4 Cu1 112.65(18) . . ? N3 O4 Cu2 110.38(18) . . ? Cu1 O4 Cu2 111.97(12) . . ? C16 N4 C18 113.1(3) . . ? C16 N4 C17 108.4(3) . . ? C18 N4 C17 107.3(3) . . ? C16 N4 Cu3 110.1(2) . . ? C18 N4 Cu3 108.0(2) . . ? C17 N4 Cu3 109.8(2) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C23 N5 C19 117.1(3) . . ? C23 N5 Cu2 127.0(3) . . ? C19 N5 Cu2 115.1(3) . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? N6 N6 C21 99.7(6) 3_765 . ? C5 C6 C7 120.6(4) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? C6 C7 C2 118.9(3) . . ? C6 C7 N2 120.8(3) . . ? C2 C7 N2 120.3(3) . . ? N2 C8 H8A 109.5 . . ? N2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C24 O9 Cu3 135.1(4) . . ? C24 O9 H9 112.4 . . ? Cu3 O9 H9 112.4 . . ? N2 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N2 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O3 C10 N3 123.1(3) . . ? O3 C10 C11 119.0(3) . . ? N3 C10 C11 117.7(3) . . ? C12 C11 C16 118.0(3) . . ? C12 C11 C10 115.9(3) . . ? C16 C11 C10 126.0(3) . . ? C13 C12 C11 121.8(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C14 C13 C12 119.9(4) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C13 C14 C15 120.2(4) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C14 C15 C16 120.7(3) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C15 C16 C11 119.4(3) . . ? C15 C16 N4 120.3(3) . . ? C11 C16 N4 120.2(3) . . ? N4 C17 H17A 109.5 . . ? N4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N4 C18 H18A 109.5 . . ? N4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N5 C19 C20 122.5(4) . . ? N5 C19 H19 118.8 . . ? C20 C19 H19 118.8 . . ? C21 C20 C19 118.9(4) . . ? C21 C20 H20 120.5 . . ? C19 C20 H20 120.5 . . ? C22 C21 C20 118.6(4) . . ? C22 C21 N6 110.9(4) . . ? C20 C21 N6 130.5(4) . . ? C21 C22 C23 119.0(4) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? N5 C23 C22 123.8(4) . . ? N5 C23 H23 118.1 . . ? C22 C23 H23 118.1 . . ? O9 C24 H24A 109.5 . . ? O9 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O9 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.869 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 936487' ####################################################################### # # 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_tw21c1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu5]' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C40 H47 Cl2 Cu5 N12 O20' _chemical_formula_weight 1404.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.3958(19) _cell_length_b 26.777(5) _cell_length_c 10.690(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.54(3) _cell_angle_gamma 90.00 _cell_volume 2644.2(9) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0 _cell_measurement_reflns_used 4818 _cell_measurement_theta_min 2.9881 _cell_measurement_theta_max 25.35 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1420 _exptl_absorpt_coefficient_mu 2.166 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.89767 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 20540 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.04 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 0.0096260000 _diffrn_orient_matrix_UB_12 0.0187120000 _diffrn_orient_matrix_UB_21 0.0172160000 _diffrn_orient_matrix_UB_22 -0.0186543000 _diffrn_orient_matrix_UB_23 -0.0419350000 _diffrn_orient_matrix_UB_31 -0.0741910000 _diffrn_orient_matrix_UB_32 -0.0019015000 _diffrn_orient_matrix_UB_33 -0.0283153000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -84.00 -43.00 1.0000 54.0000 omega____ theta____ kappa____ phi______ frames - -14.4216 179.0000 150.0000 41 #__ type_ start__ end____ width___ exp.time_ 2 omega 29.00 91.00 1.0000 54.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 37.0000 -150.0000 62 #__ type_ start__ end____ width___ exp.time_ 3 omega -50.00 7.00 1.0000 54.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 -37.0000 30.0000 57 #__ type_ start__ end____ width___ exp.time_ 4 omega 42.00 80.00 1.0000 54.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 -125.0000 -173.0000 38 #__ type_ start__ end____ width___ exp.time_ 5 omega -3.00 92.00 1.0000 54.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 37.0000 150.0000 95 #__ type_ start__ end____ width___ exp.time_ 6 omega -2.00 81.00 1.0000 54.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 -126.0000 6.0000 83 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150.0 _reflns_number_total 7736 _reflns_number_gt 5930 _reflns_threshold_expression >2sigma(I) _computing_structure_solution SHELXS97 _computing_structure_refinement 'SHELXL-97/2 (Sheldrick,1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _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^)+(0.0151P)^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 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 -0.013(13) _chemical_absolute_configuration ad _refine_ls_number_reflns 7736 _refine_ls_number_parameters 709 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.0758 _refine_ls_wR_factor_gt 0.0686 _refine_ls_goodness_of_fit_ref 0.963 _refine_ls_restrained_S_all 0.963 _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 0.40216(8) 0.43322(4) 0.49244(9) 0.0146(2) Uani 1 1 d . . . Cl1 Cl 0.07819(19) 0.46760(9) 0.13328(19) 0.0245(5) Uani 1 1 d . . . O1 O 0.2464(5) 0.28956(19) 0.3442(5) 0.0173(13) Uani 1 1 d . . . N1 N 0.3476(6) 0.3620(2) 0.2910(6) 0.0139(15) Uani 1 1 d . . . C1 C 0.3151(7) 0.3152(3) 0.2705(7) 0.0158(19) Uani 1 1 d . . . Cu2 Cu 0.20767(9) 0.33058(3) 0.48645(9) 0.0156(2) Uani 1 1 d . . . Cl2 Cl 0.5498(2) 0.23171(8) 0.5886(2) 0.0295(5) Uani 1 1 d . . . O2 O 0.2937(5) 0.38117(19) 0.3956(5) 0.0167(13) Uani 1 1 d . . . N2 N 0.3900(6) 0.3701(2) 0.0476(5) 0.0170(15) Uani 1 1 d . . . H2A H 0.2941 0.3778 0.0194 0.020 Uiso 1 1 calc R . . H2B H 0.4405 0.3807 -0.0135 0.020 Uiso 1 1 calc R . . C2 C 0.3657(7) 0.2906(3) 0.1612(7) 0.0153(18) Uani 1 1 d . . . Cu3 Cu 0.45930(9) 0.40812(3) 0.20556(8) 0.0155(2) Uani 1 1 d . . . O3 O 0.5425(4) 0.4667(2) 0.1355(4) 0.0141(12) Uani 1 1 d . . . N3 N 0.5496(6) 0.4957(2) 0.3381(6) 0.0157(16) Uani 1 1 d . . . C3 C 0.3808(7) 0.2389(3) 0.1655(7) 0.0222(19) Uani 1 1 d . . . H3 H 0.3546 0.2209 0.2344 0.027 Uiso 1 1 calc R . . Cu4 Cu 0.54787(8) 0.54327(3) 0.47731(8) 0.0156(2) Uani 1 1 d . . . O4 O 0.5075(5) 0.44647(18) 0.3596(5) 0.0130(12) Uani 1 1 d . . . N4 N 0.5384(6) 0.5982(2) 0.3506(6) 0.0195(16) Uani 1 1 d . . . H4A H 0.4431 0.6017 0.3117 0.023 Uiso 1 1 calc R . . H4B H 0.5645 0.6273 0.3948 0.023 Uiso 1 1 calc R . . C4 C 0.4332(8) 0.2133(3) 0.0710(8) 0.031(2) Uani 1 1 d . . . H4 H 0.4407 0.1779 0.0735 0.038 Uiso 1 1 calc R . . Cu5 Cu 0.29569(9) 0.46686(4) 0.75836(9) 0.0159(2) Uani 1 1 d . . . O5 O 0.4972(5) 0.5849(2) 0.6114(5) 0.0207(14) Uani 1 1 d . . . N5 N 0.4181(6) 0.5106(3) 0.6766(6) 0.0174(16) Uani 1 1 d . . . C5 C 0.4746(8) 0.2402(3) -0.0275(8) 0.034(2) Uani 1 1 d . . . H5 H 0.5152 0.2231 -0.0905 0.040 Uiso 1 1 calc R . . O6 O 0.4894(4) 0.49062(18) 0.5833(4) 0.0131(12) Uani 1 1 d . . . N6 N 0.3398(6) 0.5118(2) 0.9092(6) 0.0189(16) Uani 1 1 d . . . H6A H 0.2859 0.5018 0.9685 0.023 Uiso 1 1 calc R . . H6B H 0.4360 0.5084 0.9454 0.023 Uiso 1 1 calc R . . C6 C 0.4575(8) 0.2917(3) -0.0352(8) 0.026(2) Uani 1 1 d . . . H6 H 0.4830 0.3095 -0.1048 0.032 Uiso 1 1 calc R . . O7 O 0.1975(4) 0.4112(2) 0.8220(5) 0.0171(13) Uani 1 1 d . . . N7 N 0.2182(6) 0.3776(2) 0.6305(6) 0.0146(15) Uani 1 1 d . . . C7 C 0.4033(7) 0.3169(3) 0.0584(7) 0.0131(18) Uani 1 1 d . . . O8 O 0.2801(5) 0.42490(19) 0.6129(4) 0.0173(12) Uani 1 1 d . . . N8 N 0.1806(6) 0.2754(2) 0.6065(6) 0.0217(17) Uani 1 1 d . . . H8A H 0.1408 0.2487 0.5581 0.026 Uiso 1 1 calc R . . H8B H 0.2711 0.2656 0.6474 0.026 Uiso 1 1 calc R . . C8 C 0.5666(7) 0.5025(3) 0.2205(7) 0.0134(18) Uani 1 1 d . . . O9 O 0.0394(6) 0.4857(2) 0.2483(5) 0.0367(17) Uani 1 1 d . . . N9 N 0.6961(6) 0.3654(3) 0.2557(6) 0.0205(16) Uani 1 1 d . . . C9 C 0.6296(6) 0.5510(3) 0.1857(7) 0.0163(19) Uani 1 1 d . . . O10 O 0.0488(6) 0.4159(2) 0.1194(6) 0.0485(18) Uani 1 1 d . . . N10 N 0.9689(6) 0.3397(2) 0.3944(6) 0.0191(16) Uani 1 1 d . . . C10 C 0.7101(7) 0.5494(3) 0.0892(7) 0.0221(19) Uani 1 1 d . . . H10 H 0.7144 0.5194 0.0426 0.027 Uiso 1 1 calc R . . O11 O 0.2307(5) 0.4747(3) 0.1389(6) 0.0470(19) Uani 1 1 d . . . N11 N 0.7896(5) 0.5339(2) 0.5568(6) 0.0129(15) Uani 1 1 d . . . C11 C 0.7843(8) 0.5914(3) 0.0604(8) 0.026(2) Uani 1 1 d . . . H11 H 0.8389 0.5902 -0.0061 0.031 Uiso 1 1 calc R . . O12 O 0.0012(6) 0.4952(3) 0.0294(5) 0.054(2) Uani 1 1 d . . . N12 N 1.0677(6) 0.5064(2) 0.6714(6) 0.0170(15) Uani 1 1 d . . . C12 C 0.7787(8) 0.6339(3) 0.1270(8) 0.031(2) Uani 1 1 d . . . H12 H 0.8308 0.6624 0.1077 0.037 Uiso 1 1 calc R . . O13 O 0.5037(6) 0.2756(2) 0.6493(6) 0.0433(17) Uani 1 1 d . . . C13 C 0.6985(7) 0.6366(3) 0.2229(7) 0.0215(19) Uani 1 1 d . . . H13 H 0.6945 0.6669 0.2683 0.026 Uiso 1 1 calc R . . O14 O 0.6304(6) 0.2006(2) 0.6843(7) 0.064(2) Uani 1 1 d . . . C14 C 0.6231(7) 0.5945(3) 0.2528(7) 0.0120(17) Uani 1 1 d . . . O15 O 0.4229(5) 0.2046(2) 0.5309(5) 0.0379(16) Uani 1 1 d . . . C15 C 0.4286(7) 0.5597(3) 0.6818(7) 0.0125(18) Uani 1 1 d . . . O16 O 0.6335(6) 0.2448(3) 0.4996(7) 0.077(3) Uani 1 1 d . . . C16 C 0.3507(7) 0.5858(3) 0.7753(8) 0.0176(19) Uani 1 1 d . . . O17 O 0.0869(5) 0.2081(2) 0.3893(5) 0.0411(16) Uiso 1 1 d . . . C17 C 0.3148(7) 0.6354(3) 0.7466(8) 0.030(2) Uani 1 1 d . . . H17 H 0.3447 0.6510 0.6759 0.036 Uiso 1 1 calc R . . O18 O 0.5474(5) 0.4118(2) 0.8567(5) 0.0307(15) Uani 1 1 d . . . H18A H 0.5416 0.4025 0.7808 0.037 Uiso 1 1 calc R . . C18 C 0.2356(8) 0.6620(3) 0.8210(8) 0.033(2) Uani 1 1 d . . . H18 H 0.2095 0.6957 0.8006 0.040 Uiso 1 1 calc R . . O19 O 0.5783(5) 0.3752(2) 0.6155(6) 0.0297(14) Uani 1 1 d . . . H19A H 0.5556 0.3448 0.6086 0.036 Uiso 1 1 calc R . . C19 C 0.1947(8) 0.6396(3) 0.9244(9) 0.036(2) Uani 1 1 d . . . H19 H 0.1376 0.6575 0.9741 0.043 Uiso 1 1 calc R . . O20 O 0.2384(6) 0.5731(3) 0.3136(8) 0.060(2) Uani 1 1 d . . . H20A H 0.1953 0.5475 0.2803 0.072 Uiso 1 1 calc R . . C20 C 0.2364(8) 0.5914(3) 0.9560(8) 0.031(2) Uani 1 1 d . . . H20 H 0.2139 0.5770 1.0312 0.038 Uiso 1 1 calc R . . C21 C 0.3107(7) 0.5635(3) 0.8801(7) 0.0165(19) Uani 1 1 d . . . C22 C 0.1781(7) 0.3747(3) 0.7376(7) 0.0128(18) Uani 1 1 d . . . C23 C 0.1003(7) 0.3285(3) 0.7700(7) 0.0172(18) Uani 1 1 d . . . C24 C 0.0224(7) 0.3325(3) 0.8689(7) 0.0214(19) Uani 1 1 d . . . H24 H 0.0287 0.3624 0.9175 0.026 Uiso 1 1 calc R . . C25 C -0.0635(8) 0.2939(3) 0.8974(8) 0.028(2) Uani 1 1 d . . . H25 H -0.1142 0.2970 0.9661 0.033 Uiso 1 1 calc R . . C26 C -0.0752(7) 0.2511(3) 0.8258(8) 0.030(2) Uani 1 1 d . . . H26 H -0.1380 0.2250 0.8419 0.036 Uiso 1 1 calc R . . C27 C 0.0042(8) 0.2461(3) 0.7310(8) 0.030(2) Uani 1 1 d . . . H27 H -0.0021 0.2160 0.6832 0.036 Uiso 1 1 calc R . . C28 C 0.0930(7) 0.2840(3) 0.7038(8) 0.019(2) Uani 1 1 d . . . C29 C 0.7303(8) 0.3191(3) 0.2924(8) 0.032(2) Uani 1 1 d . . . H29 H 0.6596 0.2938 0.2700 0.038 Uiso 1 1 calc R . . C30 C 0.8636(8) 0.3058(3) 0.3617(8) 0.032(2) Uani 1 1 d . . . H30 H 0.8811 0.2720 0.3866 0.038 Uiso 1 1 calc R . . C31 C 0.9374(7) 0.3858(3) 0.3554(7) 0.023(2) Uani 1 1 d . . . H31 H 1.0093 0.4110 0.3752 0.028 Uiso 1 1 calc R . . C32 C 0.8023(7) 0.3989(3) 0.2861(7) 0.025(2) Uani 1 1 d . . . H32 H 0.7851 0.4325 0.2597 0.030 Uiso 1 1 calc R . . C33 C 0.8892(7) 0.5228(3) 0.4897(8) 0.024(2) Uani 1 1 d . . . H33 H 0.8654 0.5244 0.3995 0.029 Uiso 1 1 calc R . . C34 C 1.0280(8) 0.5089(3) 0.5465(7) 0.029(2) Uani 1 1 d . . . H34 H 1.0964 0.5010 0.4943 0.035 Uiso 1 1 calc R . . C35 C 0.9674(7) 0.5167(3) 0.7400(8) 0.031(2) Uani 1 1 d . . . H35 H 0.9903 0.5144 0.8301 0.037 Uiso 1 1 calc R . . C36 C 0.8280(8) 0.5309(3) 0.6805(7) 0.027(2) Uani 1 1 d . . . H36 H 0.7585 0.5386 0.7320 0.032 Uiso 1 1 calc R . . C37 C 0.1245(9) 0.1580(4) 0.3726(10) 0.057(3) Uiso 1 1 d . . . H37A H 0.2290 0.1536 0.4015 0.086 Uiso 1 1 calc R . . H37B H 0.0988 0.1491 0.2824 0.086 Uiso 1 1 calc R . . H37C H 0.0721 0.1363 0.4224 0.086 Uiso 1 1 calc R . . C38 C 0.7257(7) 0.3810(3) 0.6029(8) 0.036(2) Uani 1 1 d . . . H38A H 0.7503 0.4166 0.6053 0.054 Uiso 1 1 calc R . . H38B H 0.7400 0.3667 0.5218 0.054 Uiso 1 1 calc R . . H38C H 0.7883 0.3638 0.6731 0.054 Uiso 1 1 calc R . . C39 C 0.6948(8) 0.4167(4) 0.9143(8) 0.055(3) Uani 1 1 d . . . H39A H 0.7015 0.4290 1.0016 0.082 Uiso 1 1 calc R . . H39B H 0.7422 0.4405 0.8655 0.082 Uiso 1 1 calc R . . H39C H 0.7427 0.3842 0.9156 0.082 Uiso 1 1 calc R . . C40 C 0.1403(10) 0.6059(4) 0.3442(14) 0.085(5) Uani 1 1 d . . . H40A H 0.1263 0.5996 0.4315 0.128 Uiso 1 1 calc R . . H40B H 0.0479 0.6018 0.2855 0.128 Uiso 1 1 calc R . . H40C H 0.1757 0.6401 0.3379 0.128 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 0.0175(5) 0.0128(5) 0.0141(5) -0.0003(4) 0.0042(4) -0.0025(4) Cl1 0.0225(10) 0.0337(14) 0.0188(11) 0.0002(11) 0.0079(8) -0.0010(10) O1 0.020(3) 0.015(3) 0.018(3) 0.002(3) 0.007(2) 0.000(2) N1 0.013(3) 0.017(4) 0.014(4) -0.005(3) 0.007(3) -0.001(3) C1 0.010(4) 0.021(5) 0.015(5) 0.000(4) -0.002(3) 0.004(3) Cu2 0.0170(5) 0.0142(6) 0.0155(6) 0.0003(5) 0.0026(4) -0.0024(4) Cl2 0.0269(12) 0.0203(13) 0.0431(14) -0.0011(11) 0.0114(10) -0.0034(9) O2 0.021(3) 0.016(3) 0.013(3) -0.003(3) 0.005(2) 0.000(2) N2 0.021(3) 0.013(4) 0.016(4) 0.003(3) 0.000(3) -0.004(3) C2 0.014(4) 0.016(5) 0.013(4) -0.005(4) -0.003(3) 0.007(3) Cu3 0.0190(5) 0.0144(6) 0.0131(5) -0.0023(5) 0.0031(4) -0.0029(4) O3 0.011(3) 0.017(3) 0.012(3) -0.003(3) -0.003(2) 0.004(2) N3 0.012(3) 0.021(4) 0.015(4) 0.006(3) 0.005(3) -0.002(3) C3 0.027(5) 0.023(5) 0.020(5) -0.003(4) 0.011(4) 0.002(4) Cu4 0.0196(5) 0.0129(6) 0.0146(5) -0.0011(5) 0.0040(4) -0.0011(4) O4 0.019(3) 0.004(3) 0.014(3) 0.002(2) -0.001(2) -0.002(2) N4 0.029(4) 0.015(4) 0.015(4) -0.004(3) 0.003(3) 0.001(3) C4 0.037(5) 0.028(6) 0.028(5) -0.008(4) 0.002(4) -0.004(4) Cu5 0.0192(5) 0.0159(6) 0.0134(5) -0.0011(5) 0.0047(4) -0.0014(4) O5 0.021(3) 0.020(4) 0.024(3) -0.006(3) 0.012(3) -0.005(3) N5 0.019(4) 0.022(4) 0.012(4) -0.005(3) 0.004(3) 0.003(3) C5 0.039(5) 0.025(6) 0.041(6) -0.018(5) 0.017(4) 0.004(4) O6 0.015(3) 0.017(3) 0.008(3) -0.002(2) 0.004(2) 0.000(2) N6 0.019(3) 0.026(4) 0.015(4) 0.005(3) 0.012(3) -0.001(3) C6 0.029(5) 0.032(6) 0.019(5) -0.004(4) 0.004(4) -0.004(4) O7 0.013(3) 0.024(4) 0.014(3) 0.001(3) 0.001(2) -0.002(2) N7 0.021(3) 0.009(4) 0.016(4) -0.008(3) 0.009(3) -0.002(3) C7 0.006(3) 0.020(5) 0.011(4) 0.000(4) -0.002(3) -0.008(3) O8 0.029(3) 0.005(3) 0.019(3) 0.000(3) 0.006(2) -0.002(2) N8 0.025(4) 0.026(5) 0.014(4) -0.003(3) 0.002(3) -0.006(3) C8 0.003(4) 0.023(5) 0.013(5) 0.002(4) -0.002(3) 0.002(3) O9 0.057(4) 0.040(5) 0.019(3) -0.009(3) 0.024(3) 0.000(3) N9 0.010(3) 0.022(4) 0.028(4) 0.006(4) 0.000(3) -0.001(3) C9 0.004(3) 0.019(5) 0.022(5) 0.009(4) -0.005(3) -0.001(3) O10 0.072(4) 0.030(4) 0.048(4) -0.005(4) 0.023(3) -0.016(3) N10 0.017(3) 0.019(4) 0.021(4) -0.007(3) 0.002(3) 0.001(3) C10 0.028(4) 0.024(5) 0.012(4) -0.002(4) -0.002(3) -0.002(4) O11 0.026(3) 0.069(5) 0.047(4) 0.018(4) 0.010(3) -0.002(3) N11 0.011(3) 0.017(4) 0.012(4) -0.002(3) 0.007(3) 0.001(3) C11 0.033(5) 0.024(6) 0.028(5) 0.005(5) 0.023(4) -0.003(4) O12 0.050(4) 0.084(6) 0.027(4) 0.023(4) 0.004(3) 0.030(4) N12 0.018(3) 0.018(4) 0.015(4) -0.004(3) 0.003(3) -0.001(3) C12 0.027(5) 0.021(6) 0.045(6) 0.005(5) 0.008(4) -0.004(4) O13 0.046(4) 0.027(4) 0.056(5) -0.012(4) 0.007(3) -0.002(3) C13 0.030(5) 0.009(5) 0.027(5) -0.005(4) 0.009(4) 0.005(4) O14 0.041(4) 0.028(4) 0.107(6) 0.005(4) -0.029(4) 0.001(3) C14 0.016(4) 0.007(4) 0.011(4) 0.007(4) -0.001(3) 0.002(3) O15 0.032(3) 0.034(4) 0.043(4) 0.007(3) -0.004(3) -0.004(3) C15 0.009(4) 0.022(5) 0.008(4) -0.003(4) 0.003(3) 0.002(3) O16 0.083(5) 0.088(7) 0.078(6) -0.014(5) 0.061(4) -0.028(5) C16 0.012(4) 0.015(5) 0.027(5) -0.006(4) 0.005(3) 0.001(3) C17 0.025(5) 0.040(7) 0.027(5) -0.015(5) 0.009(4) -0.002(4) O18 0.029(3) 0.044(4) 0.020(3) -0.001(3) 0.007(2) 0.004(3) C18 0.040(5) 0.012(5) 0.048(6) -0.005(5) 0.011(5) 0.007(4) O19 0.029(3) 0.024(4) 0.036(4) -0.001(3) 0.007(3) 0.004(3) C19 0.039(5) 0.032(6) 0.042(6) -0.011(5) 0.020(4) 0.010(4) O20 0.040(4) 0.051(5) 0.091(6) -0.035(5) 0.017(4) -0.021(4) C20 0.034(5) 0.031(6) 0.030(5) -0.005(5) 0.007(4) -0.005(4) C21 0.018(4) 0.024(5) 0.006(4) -0.009(4) -0.001(3) 0.000(4) C22 0.010(4) 0.012(5) 0.015(5) 0.001(4) -0.002(3) 0.007(3) C23 0.013(4) 0.023(5) 0.014(4) 0.002(4) -0.001(3) -0.002(4) C24 0.025(4) 0.023(5) 0.018(5) 0.003(4) 0.009(3) 0.002(4) C25 0.022(5) 0.025(6) 0.037(6) 0.008(5) 0.009(4) -0.005(4) C26 0.029(5) 0.021(6) 0.040(6) 0.004(5) 0.006(4) -0.022(4) C27 0.038(5) 0.021(6) 0.030(5) 0.003(4) 0.008(4) -0.005(4) C28 0.006(4) 0.030(6) 0.020(5) 0.013(4) 0.000(3) 0.003(4) C29 0.022(5) 0.025(6) 0.043(6) -0.010(5) -0.008(4) -0.009(4) C30 0.025(5) 0.016(5) 0.055(7) 0.008(5) 0.008(4) 0.005(4) C31 0.015(4) 0.030(6) 0.024(5) 0.010(4) 0.001(4) -0.015(4) C32 0.024(4) 0.025(5) 0.027(5) 0.013(4) 0.006(4) 0.003(4) C33 0.020(4) 0.028(5) 0.022(5) 0.003(4) -0.002(4) -0.004(4) C34 0.036(5) 0.040(6) 0.013(5) 0.008(4) 0.010(4) 0.007(4) C35 0.019(4) 0.057(7) 0.018(5) 0.007(5) 0.004(4) 0.013(4) C36 0.027(5) 0.038(6) 0.016(5) -0.002(4) 0.005(4) 0.003(4) C38 0.033(5) 0.049(7) 0.030(6) -0.002(5) 0.017(4) 0.009(5) C39 0.041(6) 0.081(10) 0.043(6) -0.045(7) 0.006(5) -0.013(6) C40 0.045(7) 0.045(9) 0.171(15) 0.014(9) 0.033(8) -0.004(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O8 1.888(4) . ? Cu1 O4 1.907(5) . ? Cu1 O2 1.915(5) . ? Cu1 O6 1.920(5) . ? Cl1 O10 1.413(6) . ? Cl1 O12 1.417(6) . ? Cl1 O9 1.429(5) . ? Cl1 O11 1.436(5) . ? O1 C1 1.301(8) . ? O1 Cu2 1.963(5) . ? N1 C1 1.299(10) . ? N1 O2 1.407(7) . ? N1 Cu3 1.952(6) . ? C1 C2 1.494(10) . ? Cu2 O2 1.928(5) . ? Cu2 N7 1.978(6) . ? Cu2 N8 2.003(6) . ? Cu2 N10 2.292(6) 1_455 ? Cl2 O16 1.386(6) . ? Cl2 O14 1.425(6) . ? Cl2 O15 1.436(5) . ? Cl2 O13 1.447(6) . ? N2 C7 1.433(9) . ? N2 Cu3 1.977(6) . ? N2 H2A 0.9200 . ? N2 H2B 0.9200 . ? C2 C3 1.389(11) . ? C2 C7 1.405(10) . ? Cu3 O4 1.923(5) . ? Cu3 O3 1.962(5) . ? Cu3 N9 2.471(6) . ? O3 C8 1.310(9) . ? N3 C8 1.309(9) . ? N3 O4 1.406(7) . ? N3 Cu4 1.962(6) . ? C3 C4 1.384(10) . ? C3 H3 0.9500 . ? Cu4 O5 1.942(5) . ? Cu4 O6 1.950(5) . ? Cu4 N4 1.991(6) . ? Cu4 N11 2.289(5) . ? N4 C14 1.429(8) . ? N4 H4A 0.9200 . ? N4 H4B 0.9200 . ? C4 C5 1.389(11) . ? C4 H4 0.9500 . ? Cu5 O8 1.902(5) . ? Cu5 O7 1.940(5) . ? Cu5 N5 1.957(6) . ? Cu5 N6 1.994(6) . ? Cu5 N12 2.418(6) 1_455 ? O5 C15 1.272(8) . ? N5 C15 1.318(10) . ? N5 O6 1.405(7) . ? C5 C6 1.389(12) . ? C5 H5 0.9500 . ? N6 C21 1.435(9) . ? N6 H6A 0.9200 . ? N6 H6B 0.9200 . ? C6 C7 1.379(10) . ? C6 H6 0.9500 . ? O7 C22 1.320(8) . ? N7 C22 1.271(9) . ? N7 O8 1.419(7) . ? N8 C28 1.458(9) . ? N8 H8A 0.9200 . ? N8 H8B 0.9200 . ? C8 C9 1.503(10) . ? N9 C29 1.322(10) . ? N9 C32 1.336(9) . ? C9 C14 1.376(10) . ? C9 C10 1.388(9) . ? N10 C31 1.321(9) . ? N10 C30 1.340(9) . ? N10 Cu2 2.292(5) 1_655 ? C10 C11 1.387(11) . ? C10 H10 0.9500 . ? N11 C36 1.308(9) . ? N11 C33 1.313(8) . ? C11 C12 1.350(11) . ? C11 H11 0.9500 . ? N12 C34 1.320(9) . ? N12 C35 1.324(8) . ? N12 Cu5 2.417(6) 1_655 ? C12 C13 1.380(10) . ? C12 H12 0.9500 . ? C13 C14 1.398(10) . ? C13 H13 0.9500 . ? C15 C16 1.514(10) . ? C16 C21 1.381(10) . ? C16 C17 1.391(11) . ? O17 C37 1.409(11) . ? C17 C18 1.381(10) . ? C17 H17 0.9500 . ? O18 C39 1.415(8) . ? O18 H18A 0.8400 . ? C18 C19 1.373(11) . ? C18 H18 0.9500 . ? O19 C38 1.425(7) . ? O19 H19A 0.8400 . ? C19 C20 1.374(11) . ? C19 H19 0.9500 . ? O20 C40 1.357(11) . ? O20 H20A 0.8400 . ? C20 C21 1.382(10) . ? C20 H20 0.9500 . ? C22 C23 1.510(10) . ? C23 C28 1.380(11) . ? C23 C24 1.396(9) . ? C24 C25 1.379(10) . ? C24 H24 0.9500 . ? C25 C26 1.372(11) . ? C25 H25 0.9500 . ? C26 C27 1.370(9) . ? C26 H26 0.9500 . ? C27 C28 1.379(10) . ? C27 H27 0.9500 . ? C29 C30 1.380(10) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? C31 C32 1.391(9) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 C34 1.385(10) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.401(9) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C38 H38A 0.9800 . ? C38 H38B 0.9800 . ? C38 H38C 0.9800 . ? C39 H39A 0.9800 . ? C39 H39B 0.9800 . ? C39 H39C 0.9800 . ? C40 H40A 0.9800 . ? C40 H40B 0.9800 . ? C40 H40C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O8 Cu1 O4 173.1(2) . . ? O8 Cu1 O2 87.3(2) . . ? O4 Cu1 O2 91.7(2) . . ? O8 Cu1 O6 90.3(2) . . ? O4 Cu1 O6 89.8(2) . . ? O2 Cu1 O6 172.7(2) . . ? O10 Cl1 O12 111.5(4) . . ? O10 Cl1 O9 110.2(4) . . ? O12 Cl1 O9 108.9(4) . . ? O10 Cl1 O11 108.0(4) . . ? O12 Cl1 O11 109.0(4) . . ? O9 Cl1 O11 109.2(4) . . ? C1 O1 Cu2 110.9(5) . . ? C1 N1 O2 112.2(6) . . ? C1 N1 Cu3 131.4(5) . . ? O2 N1 Cu3 116.3(4) . . ? N1 C1 O1 122.3(7) . . ? N1 C1 C2 117.3(7) . . ? O1 C1 C2 120.3(7) . . ? O2 Cu2 O1 81.3(2) . . ? O2 Cu2 N7 88.8(2) . . ? O1 Cu2 N7 165.8(2) . . ? O2 Cu2 N8 162.7(2) . . ? O1 Cu2 N8 98.4(2) . . ? N7 Cu2 N8 88.0(3) . . ? O2 Cu2 N10 100.2(2) . 1_455 ? O1 Cu2 N10 91.9(2) . 1_455 ? N7 Cu2 N10 99.9(2) . 1_455 ? N8 Cu2 N10 97.1(2) . 1_455 ? O16 Cl2 O14 110.3(4) . . ? O16 Cl2 O15 111.3(4) . . ? O14 Cl2 O15 107.6(4) . . ? O16 Cl2 O13 110.9(4) . . ? O14 Cl2 O13 108.5(4) . . ? O15 Cl2 O13 108.1(3) . . ? N1 O2 Cu1 117.5(4) . . ? N1 O2 Cu2 112.9(4) . . ? Cu1 O2 Cu2 118.0(2) . . ? C7 N2 Cu3 115.7(5) . . ? C7 N2 H2A 108.4 . . ? Cu3 N2 H2A 108.4 . . ? C7 N2 H2B 108.4 . . ? Cu3 N2 H2B 108.4 . . ? H2A N2 H2B 107.4 . . ? C3 C2 C7 119.2(7) . . ? C3 C2 C1 117.3(7) . . ? C7 C2 C1 123.5(7) . . ? O4 Cu3 N1 90.0(2) . . ? O4 Cu3 O3 81.5(2) . . ? N1 Cu3 O3 166.0(2) . . ? O4 Cu3 N2 174.5(2) . . ? N1 Cu3 N2 87.3(3) . . ? O3 Cu3 N2 100.2(2) . . ? O4 Cu3 N9 90.0(2) . . ? N1 Cu3 N9 98.4(2) . . ? O3 Cu3 N9 92.7(2) . . ? N2 Cu3 N9 95.2(2) . . ? C8 O3 Cu3 110.5(4) . . ? C8 N3 O4 112.0(6) . . ? C8 N3 Cu4 131.1(6) . . ? O4 N3 Cu4 116.3(4) . . ? C4 C3 C2 121.1(8) . . ? C4 C3 H3 119.4 . . ? C2 C3 H3 119.4 . . ? O5 Cu4 O6 81.6(2) . . ? O5 Cu4 N3 165.9(2) . . ? O6 Cu4 N3 90.7(2) . . ? O5 Cu4 N4 95.2(2) . . ? O6 Cu4 N4 161.4(2) . . ? N3 Cu4 N4 88.3(2) . . ? O5 Cu4 N11 98.6(2) . . ? O6 Cu4 N11 94.1(2) . . ? N3 Cu4 N11 93.7(2) . . ? N4 Cu4 N11 104.5(2) . . ? N3 O4 Cu1 119.7(4) . . ? N3 O4 Cu3 112.9(4) . . ? Cu1 O4 Cu3 117.7(2) . . ? C14 N4 Cu4 119.0(5) . . ? C14 N4 H4A 107.6 . . ? Cu4 N4 H4A 107.6 . . ? C14 N4 H4B 107.6 . . ? Cu4 N4 H4B 107.6 . . ? H4A N4 H4B 107.0 . . ? C3 C4 C5 118.9(9) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? O8 Cu5 O7 82.1(2) . . ? O8 Cu5 N5 87.3(2) . . ? O7 Cu5 N5 166.6(2) . . ? O8 Cu5 N6 172.3(2) . . ? O7 Cu5 N6 102.8(2) . . ? N5 Cu5 N6 87.0(2) . . ? O8 Cu5 N12 90.8(2) . 1_455 ? O7 Cu5 N12 91.5(2) . 1_455 ? N5 Cu5 N12 96.8(2) . 1_455 ? N6 Cu5 N12 94.9(2) . 1_455 ? C15 O5 Cu4 110.6(5) . . ? C15 N5 O6 111.6(6) . . ? C15 N5 Cu5 128.6(5) . . ? O6 N5 Cu5 119.0(5) . . ? C4 C5 C6 120.9(8) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? N5 O6 Cu1 116.7(4) . . ? N5 O6 Cu4 111.0(4) . . ? Cu1 O6 Cu4 115.1(2) . . ? C21 N6 Cu5 113.8(5) . . ? C21 N6 H6A 108.8 . . ? Cu5 N6 H6A 108.8 . . ? C21 N6 H6B 108.8 . . ? Cu5 N6 H6B 108.8 . . ? H6A N6 H6B 107.7 . . ? C7 C6 C5 119.8(8) . . ? C7 C6 H6 120.1 . . ? C5 C6 H6 120.1 . . ? C22 O7 Cu5 110.1(5) . . ? C22 N7 O8 111.7(6) . . ? C22 N7 Cu2 132.9(6) . . ? O8 N7 Cu2 115.4(4) . . ? C6 C7 C2 120.0(8) . . ? C6 C7 N2 117.9(7) . . ? C2 C7 N2 122.1(7) . . ? N7 O8 Cu1 120.7(4) . . ? N7 O8 Cu5 113.0(4) . . ? Cu1 O8 Cu5 121.5(2) . . ? C28 N8 Cu2 119.6(5) . . ? C28 N8 H8A 107.4 . . ? Cu2 N8 H8A 107.4 . . ? C28 N8 H8B 107.4 . . ? Cu2 N8 H8B 107.4 . . ? H8A N8 H8B 106.9 . . ? N3 C8 O3 121.9(7) . . ? N3 C8 C9 118.7(7) . . ? O3 C8 C9 119.1(7) . . ? C29 N9 C32 115.2(6) . . ? C29 N9 Cu3 131.2(5) . . ? C32 N9 Cu3 110.2(5) . . ? C14 C9 C10 119.8(7) . . ? C14 C9 C8 123.2(7) . . ? C10 C9 C8 116.7(8) . . ? C31 N10 C30 116.0(6) . . ? C31 N10 Cu2 112.4(5) . 1_655 ? C30 N10 Cu2 131.1(5) . 1_655 ? C11 C10 C9 120.3(8) . . ? C11 C10 H10 119.9 . . ? C9 C10 H10 119.9 . . ? C36 N11 C33 116.5(6) . . ? C36 N11 Cu4 116.9(5) . . ? C33 N11 Cu4 125.5(5) . . ? C12 C11 C10 119.8(8) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C34 N12 C35 116.8(7) . . ? C34 N12 Cu5 118.6(5) . 1_655 ? C35 N12 Cu5 123.3(5) . 1_655 ? C11 C12 C13 121.0(8) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 119.8(7) . . ? C12 C13 H13 120.1 . . ? C14 C13 H13 120.1 . . ? C9 C14 C13 119.4(7) . . ? C9 C14 N4 121.6(7) . . ? C13 C14 N4 119.0(7) . . ? O5 C15 N5 123.1(7) . . ? O5 C15 C16 120.3(7) . . ? N5 C15 C16 116.6(7) . . ? C21 C16 C17 120.0(7) . . ? C21 C16 C15 124.9(7) . . ? C17 C16 C15 115.0(7) . . ? C18 C17 C16 120.0(8) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C39 O18 H18A 109.5 . . ? C19 C18 C17 119.9(8) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C38 O19 H19A 109.5 . . ? C18 C19 C20 119.9(8) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C40 O20 H20A 109.5 . . ? C19 C20 C21 121.1(8) . . ? C19 C20 H20 119.5 . . ? C21 C20 H20 119.5 . . ? C16 C21 C20 119.0(8) . . ? C16 C21 N6 121.6(7) . . ? C20 C21 N6 119.4(7) . . ? N7 C22 O7 122.9(7) . . ? N7 C22 C23 119.6(7) . . ? O7 C22 C23 117.5(7) . . ? C28 C23 C24 118.1(7) . . ? C28 C23 C22 124.8(7) . . ? C24 C23 C22 116.9(7) . . ? C25 C24 C23 121.2(8) . . ? C25 C24 H24 119.4 . . ? C23 C24 H24 119.4 . . ? C26 C25 C24 119.6(8) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C27 C26 C25 119.7(7) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 121.1(8) . . ? C26 C27 H27 119.5 . . ? C28 C27 H27 119.5 . . ? C27 C28 C23 120.2(7) . . ? C27 C28 N8 118.4(8) . . ? C23 C28 N8 121.4(7) . . ? N9 C29 C30 123.3(8) . . ? N9 C29 H29 118.3 . . ? C30 C29 H29 118.3 . . ? N10 C30 C29 121.3(8) . . ? N10 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? N10 C31 C32 122.2(7) . . ? N10 C31 H31 118.9 . . ? C32 C31 H31 118.9 . . ? N9 C32 C31 122.0(8) . . ? N9 C32 H32 119.0 . . ? C31 C32 H32 119.0 . . ? N11 C33 C34 122.0(7) . . ? N11 C33 H33 119.0 . . ? C34 C33 H33 119.0 . . ? N12 C34 C33 121.8(7) . . ? N12 C34 H34 119.1 . . ? C33 C34 H34 119.1 . . ? N12 C35 C36 120.4(7) . . ? N12 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? N11 C36 C35 122.5(7) . . ? N11 C36 H36 118.7 . . ? C35 C36 H36 118.7 . . ? O17 C37 H37A 109.5 . . ? O17 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O17 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O19 C38 H38A 109.5 . . ? O19 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? O19 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? O18 C39 H39A 109.5 . . ? O18 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O18 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? O20 C40 H40A 109.5 . . ? O20 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? O20 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.525 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 936488' ####################################################################### # # 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_tw19a2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '[Cu5]' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H40 Cl2 Cu5 N8 O21' _chemical_formula_weight 1261.32 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 triclinic _symmetry_space_group_name_H-M P-1 _space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.0640(3) _cell_length_b 12.2750(4) _cell_length_c 17.2399(6) _cell_angle_alpha 110.321(3) _cell_angle_beta 96.075(3) _cell_angle_gamma 96.316(2) _cell_volume 2156.10(12) _cell_formula_units_Z 2 _cell_measurement_temperature 150.0 _cell_measurement_reflns_used 8283 _cell_measurement_theta_min 2.8605 _cell_measurement_theta_max 25.35 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Green _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.943 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1270 _exptl_absorpt_coefficient_mu 2.643 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) ; _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.95013 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) (compiled Aug 2 2010,13:00:58) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_detector_area_resol_mean 16.1048 _diffrn_reflns_number 17735 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.35 _diffrn_orient_matrix_UB_11 0.0348869000 _diffrn_orient_matrix_UB_12 -0.0429343000 _diffrn_orient_matrix_UB_21 -0.0510412000 _diffrn_orient_matrix_UB_22 -0.0269626000 _diffrn_orient_matrix_UB_23 -0.0323203000 _diffrn_orient_matrix_UB_31 0.0209707000 _diffrn_orient_matrix_UB_32 0.0363739000 _diffrn_orient_matrix_UB_33 -0.0216147000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -17.00 58.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -14.2653 37.0000 30.0000 75 #__ type_ start__ end____ width___ exp.time_ 2 omega -58.00 -32.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - -14.2653 179.0000 150.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega -1.00 91.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 77.0000 -90.0000 92 #__ type_ start__ end____ width___ exp.time_ 4 omega -41.00 53.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 -77.0000 150.0000 94 #__ type_ start__ end____ width___ exp.time_ 5 omega 1.00 33.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 83.0000 4.0000 32 #__ type_ start__ end____ width___ exp.time_ 6 omega 13.00 84.00 1.0000 40.0000 omega____ theta____ kappa____ phi______ frames - 22.7028 77.0000 60.0000 71 ; _diffrn_measurement_method '\w scans' _diffrn_ambient_temperature 150.0 _reflns_number_total 7876 _reflns_number_gt 6482 _reflns_threshold_expression >2sigma(I) _computing_structure_solution ; SHELXS-97, Sheldrick, G.M. (2008) Acta Crystallogr.,D64,112-122 ; _computing_structure_refinement ; SHELXL-97/2, G.M. Sheldrick, G.M. (2008) Acta Crystallogr.,D64,112-122 ; _computing_molecular_graphics ; ORTEX, McArdle, P. (1995) J.Appl.Cryst.,28,65-65 ; _computing_publication_material ; Ciftab, G.M. Sheldrick, G.M. (2008) Acta Crystallogr.,D64,112-122 ; _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^)+(0.0319P)^2^+2.2190P] 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 7876 _refine_ls_number_parameters 614 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0322 _refine_ls_wR_factor_ref 0.0795 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 1.0000 0.5000 0.5000 0.01357(14) Uani 1 2 d S . . Cu2 Cu 0.89563(4) 0.22818(3) 0.47163(2) 0.01388(10) Uani 1 1 d . . . Cu3 Cu 1.08781(4) 0.41157(4) 0.31518(2) 0.01379(10) Uani 1 1 d . . . Cu4 Cu 0.5000 0.0000 0.0000 0.01340(14) Uani 1 2 d S . . Cu5 Cu 0.53564(4) 0.03042(4) 0.19700(2) 0.01499(11) Uani 1 1 d . . . Cu6 Cu 0.66406(4) 0.25537(3) 0.04758(2) 0.01336(10) Uani 1 1 d . . . Cl1 Cl 0.25431(8) 0.10762(8) 0.44326(5) 0.01847(19) Uani 1 1 d . . . Cl2 Cl 0.63566(9) -0.28584(8) -0.08899(5) 0.0199(2) Uani 1 1 d . . . O1 O 1.0123(2) 0.2450(2) 0.25436(13) 0.0160(5) Uani 1 1 d . . . O2 O 1.0255(2) 0.3783(2) 0.40433(14) 0.0187(6) Uani 1 1 d . . . O3 O 1.1223(2) 0.7764(2) 0.41955(14) 0.0173(5) Uani 1 1 d . . . O4 O 1.1124(2) 0.60646(19) 0.47148(13) 0.0144(5) Uani 1 1 d . . . O5 O 1.2761(2) 0.3536(2) 0.34793(16) 0.0253(6) Uani 1 1 d . . . H5 H 1.2761 0.2712 0.3311 0.030 Uiso 1 1 calc R . . O6 O 0.6886(2) 0.1697(2) 0.41562(14) 0.0193(6) Uani 1 1 d . . . H6 H 0.6581 0.1150 0.3607 0.023 Uiso 1 1 calc R . . O7 O 0.4033(2) -0.10576(19) 0.03556(13) 0.0152(5) Uani 1 1 d . . . O8 O 0.3434(2) -0.3008(2) 0.05000(14) 0.0171(5) Uani 1 1 d . . . O9 O 0.6298(2) 0.1860(2) 0.26401(13) 0.0159(5) Uani 1 1 d . . . O10 O 0.5941(2) 0.07362(19) 0.10947(13) 0.0154(5) Uani 1 1 d . . . O11 O 0.3494(3) 0.1158(2) 0.22607(16) 0.0269(6) Uani 1 1 d . . . H11A H 0.3552 0.1918 0.2678 0.032 Uiso 1 1 calc R . . O12 O 0.3066(3) 0.2271(2) 0.45946(17) 0.0307(7) Uani 1 1 d . . . O13 O 0.3492(3) 0.0383(3) 0.44300(19) 0.0367(7) Uani 1 1 d . . . O14 O 0.1815(3) 0.1065(2) 0.50798(16) 0.0279(6) Uani 1 1 d . . . O15 O 0.1745(3) 0.0612(3) 0.36408(16) 0.0381(8) Uani 1 1 d . . . O16 O 0.5277(3) -0.3449(3) -0.07235(18) 0.0336(7) Uani 1 1 d . . . O17 O 0.6449(3) -0.1607(2) -0.04916(15) 0.0280(7) Uani 1 1 d . . . O18 O 0.7431(3) -0.3232(3) -0.05780(17) 0.0308(7) Uani 1 1 d . . . O19 O 0.6289(3) -0.3168(2) -0.17833(15) 0.0282(7) Uani 1 1 d . . . O20 O 0.9778(3) 0.2546(2) 0.09989(15) 0.0235(6) Uiso 1 1 d . . . H20A H 0.9946 0.2361 0.1419 0.028 Uiso 1 1 calc R . . N1 N 0.9177(3) 0.0625(2) 0.41392(16) 0.0144(6) Uani 1 1 d . . . H1A H 1.0000 0.0576 0.4228 0.017 Uiso 1 1 calc R . . H1B H 0.8769 0.0166 0.4383 0.017 Uiso 1 1 calc R . . N2 N 0.9630(3) 0.2644(2) 0.38235(17) 0.0150(6) Uani 1 1 d . . . N3 N 1.1534(3) 0.4519(2) 0.22432(17) 0.0162(6) Uani 1 1 d . . . H3A H 1.2379 0.4603 0.2349 0.019 Uiso 1 1 calc R . . H3B H 1.1278 0.3883 0.1753 0.019 Uiso 1 1 calc R . . N4 N 1.1179(3) 0.5787(2) 0.38507(16) 0.0140(6) Uani 1 1 d . . . N5 N 0.4940(3) -0.0278(2) 0.28678(17) 0.0198(7) Uani 1 1 d . . . H5A H 0.5525 0.0116 0.3332 0.024 Uiso 1 1 calc R . . H5B H 0.4202 -0.0050 0.3004 0.024 Uiso 1 1 calc R . . N6 N 0.4426(3) -0.1130(2) 0.11424(16) 0.0152(6) Uani 1 1 d . . . N7 N 0.7789(3) 0.3928(3) 0.12669(17) 0.0172(6) Uani 1 1 d . . . H7A H 0.8570 0.3750 0.1220 0.021 Uiso 1 1 calc R . . H7B H 0.7728 0.4536 0.1076 0.021 Uiso 1 1 calc R . . N8 N 0.6508(3) 0.1904(2) 0.13538(17) 0.0141(6) Uani 1 1 d . . . C1 C 0.8744(3) 0.0130(3) 0.3239(2) 0.0148(7) Uani 1 1 d . . . C2 C 0.8086(3) -0.0997(3) 0.2900(2) 0.0184(8) Uani 1 1 d . . . H2 H 0.7923 -0.1422 0.3255 0.022 Uiso 1 1 calc R . . C3 C 0.7664(4) -0.1515(3) 0.2048(2) 0.0222(8) Uani 1 1 d . . . H3 H 0.7198 -0.2283 0.1822 0.027 Uiso 1 1 calc R . . C4 C 0.7923(4) -0.0908(3) 0.1528(2) 0.0224(9) Uani 1 1 d . . . H4 H 0.7650 -0.1262 0.0942 0.027 Uiso 1 1 calc R . . C5 C 0.8579(3) 0.0212(3) 0.1866(2) 0.0194(8) Uani 1 1 d . . . H1 H 0.8755 0.0622 0.1504 0.023 Uiso 1 1 calc R . . C6 C 0.8996(3) 0.0768(3) 0.2726(2) 0.0144(7) Uani 1 1 d . . . C7 C 0.9626(3) 0.2006(3) 0.30392(19) 0.0140(7) Uani 1 1 d . . . C8 C 1.1225(3) 0.5552(3) 0.2095(2) 0.0143(7) Uani 1 1 d . . . C9 C 1.1004(3) 0.5501(3) 0.1279(2) 0.0187(8) Uani 1 1 d . . . H9 H 1.1046 0.4792 0.0832 0.022 Uiso 1 1 calc R . . C10 C 1.0719(4) 0.6475(3) 0.1103(2) 0.0241(9) Uani 1 1 d . . . H10 H 1.0547 0.6423 0.0538 0.029 Uiso 1 1 calc R . . C11 C 1.0688(4) 0.7510(3) 0.1743(2) 0.0235(9) Uani 1 1 d . . . H11 H 1.0513 0.8182 0.1625 0.028 Uiso 1 1 calc R . . C12 C 1.0912(3) 0.7570(3) 0.2566(2) 0.0186(8) Uani 1 1 d . . . H12 H 1.0898 0.8293 0.3007 0.022 Uiso 1 1 calc R . . C13 C 1.1158(3) 0.6601(3) 0.2763(2) 0.0139(7) Uani 1 1 d . . . C14 C 1.1218(3) 0.6726(3) 0.3655(2) 0.0147(7) Uani 1 1 d . . . C15 C 1.3887(4) 0.4257(4) 0.3893(3) 0.0408(11) Uani 1 1 d . . . H15A H 1.3923 0.5004 0.3801 0.061 Uiso 1 1 calc R . . H15B H 1.4567 0.3861 0.3671 0.061 Uiso 1 1 calc R . . H15C H 1.3956 0.4409 0.4494 0.061 Uiso 1 1 calc R . . C16 C 0.6132(4) 0.2271(4) 0.4747(2) 0.0315(10) Uani 1 1 d . . . H16A H 0.6132 0.1933 0.5185 0.047 Uiso 1 1 calc R . . H16B H 0.5288 0.2161 0.4461 0.047 Uiso 1 1 calc R . . H16C H 0.6457 0.3114 0.5001 0.047 Uiso 1 1 calc R . . C17 C 0.4839(3) -0.1521(3) 0.2731(2) 0.0145(7) Uani 1 1 d . . . C18 C 0.5216(3) -0.1837(3) 0.3402(2) 0.0175(8) Uani 1 1 d . . . H18 H 0.5498 -0.1240 0.3936 0.021 Uiso 1 1 calc R . . C19 C 0.5191(4) -0.3002(3) 0.3313(2) 0.0211(8) Uani 1 1 d . . . H19 H 0.5467 -0.3205 0.3778 0.025 Uiso 1 1 calc R . . C20 C 0.4758(4) -0.3874(3) 0.2534(2) 0.0248(9) Uani 1 1 d . . . H20 H 0.4740 -0.4679 0.2462 0.030 Uiso 1 1 calc R . . C21 C 0.4355(4) -0.3564(3) 0.1865(2) 0.0225(9) Uani 1 1 d . . . H21 H 0.4037 -0.4168 0.1340 0.027 Uiso 1 1 calc R . . C22 C 0.4401(3) -0.2398(3) 0.1937(2) 0.0155(7) Uani 1 1 d . . . C23 C 0.4051(3) -0.2168(3) 0.1153(2) 0.0133(7) Uani 1 1 d . . . C24 C 0.7709(3) 0.4390(3) 0.2156(2) 0.0149(7) Uani 1 1 d . . . C25 C 0.8141(3) 0.5580(3) 0.2595(2) 0.0192(8) Uani 1 1 d . . . H25 H 0.8443 0.6057 0.2304 0.023 Uiso 1 1 calc R . . C26 C 0.8138(3) 0.6080(3) 0.3447(2) 0.0205(8) Uani 1 1 d . . . H26 H 0.8435 0.6894 0.3738 0.025 Uiso 1 1 calc R . . C27 C 0.7703(3) 0.5390(3) 0.3873(2) 0.0196(8) Uani 1 1 d . . . H27 H 0.7709 0.5723 0.4460 0.023 Uiso 1 1 calc R . . C28 C 0.7257(3) 0.4209(3) 0.3437(2) 0.0172(8) Uani 1 1 d . . . H28 H 0.6954 0.3742 0.3735 0.021 Uiso 1 1 calc R . . C29 C 0.7237(3) 0.3682(3) 0.2575(2) 0.0139(7) Uani 1 1 d . . . C30 C 0.6667(3) 0.2420(3) 0.2171(2) 0.0136(7) Uani 1 1 d . . . C31 C 0.2321(4) 0.0535(4) 0.1815(3) 0.0318(10) Uani 1 1 d . . . H31A H 0.2299 0.0396 0.1218 0.048 Uiso 1 1 calc R . . H31B H 0.1681 0.1001 0.2028 0.048 Uiso 1 1 calc R . . H31C H 0.2174 -0.0220 0.1892 0.048 Uiso 1 1 calc R . . C32 C 0.9789(4) 0.1569(4) 0.0260(3) 0.0376(11) Uiso 1 1 d . . . H32A H 0.9842 0.1837 -0.0210 0.056 Uiso 1 1 calc R . . H32B H 0.9032 0.1007 0.0143 0.056 Uiso 1 1 calc R . . H32C H 1.0502 0.1188 0.0336 0.056 Uiso 1 1 calc R . . O21A O 0.6537(8) 0.5631(7) 0.0667(5) 0.023(2) Uiso 0.33 1 d P A 2 O21B O 0.7026(12) 0.5492(9) 0.0497(6) 0.026(2) Uiso 0.33 1 d P B 1 O21C O 0.7491(11) 0.5640(10) 0.0578(7) 0.039(3) Uiso 0.33 1 d P . . 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 0.0185(3) 0.0114(3) 0.0094(3) 0.0023(2) 0.0046(2) -0.0014(3) Cu2 0.0186(2) 0.0124(2) 0.0100(2) 0.00351(16) 0.00382(17) -0.00022(18) Cu3 0.0189(2) 0.0124(2) 0.0104(2) 0.00405(16) 0.00520(17) 0.00149(18) Cu4 0.0196(3) 0.0102(3) 0.0090(3) 0.0034(2) 0.0006(2) -0.0012(3) Cu5 0.0230(3) 0.0105(2) 0.0097(2) 0.00361(16) 0.00000(17) -0.00221(18) Cu6 0.0169(2) 0.0112(2) 0.0106(2) 0.00393(16) 0.00024(17) -0.00165(18) Cl1 0.0188(5) 0.0197(4) 0.0175(4) 0.0076(3) 0.0036(4) 0.0021(4) Cl2 0.0237(5) 0.0201(5) 0.0192(4) 0.0082(4) 0.0081(4) 0.0088(4) O1 0.0211(14) 0.0162(13) 0.0112(12) 0.0052(10) 0.0056(10) 0.0012(11) O2 0.0273(15) 0.0109(12) 0.0140(12) 0.0014(9) 0.0073(11) -0.0057(11) O3 0.0268(15) 0.0131(12) 0.0123(12) 0.0045(10) 0.0056(11) 0.0023(11) O4 0.0222(14) 0.0135(12) 0.0070(11) 0.0035(9) 0.0039(10) -0.0009(11) O5 0.0217(15) 0.0242(15) 0.0327(15) 0.0140(12) 0.0012(12) 0.0046(12) O6 0.0188(14) 0.0224(14) 0.0129(12) 0.0025(10) 0.0015(10) 0.0013(11) O7 0.0243(14) 0.0120(12) 0.0081(11) 0.0044(9) -0.0012(10) -0.0016(11) O8 0.0226(15) 0.0139(12) 0.0123(12) 0.0048(10) -0.0006(10) -0.0048(11) O9 0.0214(14) 0.0135(12) 0.0114(12) 0.0043(9) 0.0013(10) -0.0017(11) O10 0.0235(14) 0.0080(12) 0.0122(12) 0.0034(9) -0.0011(10) -0.0036(10) O11 0.0287(17) 0.0197(14) 0.0282(15) 0.0046(11) 0.0015(12) 0.0039(12) O12 0.0325(18) 0.0215(15) 0.0399(17) 0.0138(12) 0.0097(14) -0.0017(13) O13 0.0288(18) 0.0303(16) 0.055(2) 0.0164(14) 0.0099(15) 0.0135(14) O14 0.0322(17) 0.0305(15) 0.0233(14) 0.0122(12) 0.0120(12) -0.0005(13) O15 0.0352(19) 0.054(2) 0.0192(15) 0.0099(13) -0.0012(13) -0.0017(16) O16 0.0288(17) 0.0363(17) 0.0485(18) 0.0246(14) 0.0200(14) 0.0135(14) O17 0.0395(18) 0.0200(14) 0.0209(14) 0.0020(11) 0.0044(12) 0.0089(13) O18 0.0277(17) 0.0383(17) 0.0316(16) 0.0141(13) 0.0085(13) 0.0177(14) O19 0.0460(19) 0.0212(14) 0.0173(13) 0.0057(11) 0.0079(13) 0.0072(14) N1 0.0130(16) 0.0166(15) 0.0145(15) 0.0071(12) 0.0023(12) 0.0005(13) N2 0.0212(17) 0.0076(14) 0.0144(15) 0.0028(11) 0.0034(13) -0.0024(13) N3 0.0201(17) 0.0180(15) 0.0134(14) 0.0070(12) 0.0067(13) 0.0067(13) N4 0.0175(16) 0.0159(15) 0.0080(14) 0.0035(11) 0.0038(12) 0.0013(13) N5 0.032(2) 0.0143(15) 0.0111(14) 0.0034(12) 0.0030(13) 0.0003(14) N6 0.0217(17) 0.0145(15) 0.0093(14) 0.0057(11) 0.0009(12) -0.0005(13) N7 0.0177(17) 0.0168(15) 0.0154(15) 0.0067(12) 0.0009(12) -0.0048(13) N8 0.0163(16) 0.0080(14) 0.0166(15) 0.0046(11) -0.0006(12) -0.0008(12) C1 0.0125(19) 0.0155(18) 0.0155(17) 0.0038(14) 0.0036(14) 0.0035(15) C2 0.019(2) 0.0170(18) 0.0214(19) 0.0080(15) 0.0070(16) 0.0036(16) C3 0.020(2) 0.0140(18) 0.026(2) 0.0008(15) 0.0023(16) -0.0037(16) C4 0.028(2) 0.0174(19) 0.0140(18) -0.0021(14) -0.0011(16) 0.0023(17) C5 0.022(2) 0.0190(19) 0.0168(18) 0.0059(15) 0.0032(15) 0.0049(16) C6 0.0133(19) 0.0130(17) 0.0154(17) 0.0033(14) 0.0027(14) 0.0021(15) C7 0.018(2) 0.0148(18) 0.0100(16) 0.0049(13) 0.0022(14) 0.0045(15) C8 0.0103(18) 0.0187(18) 0.0157(17) 0.0084(14) 0.0054(14) -0.0005(15) C9 0.021(2) 0.0191(19) 0.0149(18) 0.0052(14) 0.0028(15) 0.0018(16) C10 0.031(2) 0.026(2) 0.0145(18) 0.0091(16) -0.0011(16) 0.0020(18) C11 0.034(2) 0.020(2) 0.0196(19) 0.0116(16) 0.0039(17) 0.0032(18) C12 0.024(2) 0.0152(18) 0.0164(18) 0.0051(14) 0.0055(15) 0.0019(16) C13 0.0120(18) 0.0165(18) 0.0116(17) 0.0030(13) 0.0031(14) 0.0010(15) C14 0.0152(19) 0.0145(18) 0.0144(17) 0.0049(14) 0.0049(14) 0.0015(15) C15 0.034(3) 0.046(3) 0.046(3) 0.026(2) -0.002(2) -0.003(2) C16 0.020(2) 0.037(2) 0.031(2) 0.0048(19) 0.0070(18) 0.0014(19) C17 0.0137(19) 0.0145(18) 0.0147(17) 0.0050(14) 0.0040(14) -0.0011(15) C18 0.018(2) 0.0190(19) 0.0127(17) 0.0056(14) -0.0008(14) -0.0038(16) C19 0.023(2) 0.028(2) 0.0175(19) 0.0136(16) 0.0009(16) 0.0052(17) C20 0.036(3) 0.0150(19) 0.026(2) 0.0112(16) 0.0019(18) 0.0036(18) C21 0.034(2) 0.0151(19) 0.0144(18) 0.0041(14) -0.0001(16) -0.0034(17) C22 0.017(2) 0.0162(18) 0.0136(17) 0.0073(14) 0.0032(14) -0.0010(15) C23 0.0113(18) 0.0159(18) 0.0118(17) 0.0044(14) 0.0020(14) 0.0002(15) C24 0.0103(18) 0.0153(18) 0.0163(17) 0.0044(14) -0.0023(14) -0.0009(15) C25 0.016(2) 0.0169(19) 0.025(2) 0.0096(15) 0.0002(16) -0.0008(16) C26 0.019(2) 0.0117(18) 0.025(2) 0.0014(15) -0.0027(16) 0.0003(15) C27 0.020(2) 0.0182(19) 0.0158(18) 0.0005(14) 0.0019(15) 0.0039(16) C28 0.019(2) 0.0142(18) 0.0178(18) 0.0046(14) 0.0026(15) 0.0027(15) C29 0.0114(19) 0.0121(17) 0.0145(17) 0.0012(13) -0.0015(14) 0.0015(14) C30 0.0131(18) 0.0145(17) 0.0136(17) 0.0060(14) 0.0013(14) 0.0022(15) C31 0.026(2) 0.033(2) 0.033(2) 0.0086(19) 0.0047(19) 0.000(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 O2 1.874(2) . ? Cu1 O2 1.874(2) 2_766 ? Cu1 O4 1.927(2) . ? Cu1 O4 1.927(2) 2_766 ? Cu2 O3 1.926(2) 2_766 ? Cu2 O4 1.940(2) 2_766 ? Cu2 N2 1.941(3) . ? Cu2 N1 1.985(3) . ? Cu2 O6 2.320(3) . ? Cu3 O2 1.898(2) . ? Cu3 N4 1.954(3) . ? Cu3 O1 1.982(2) . ? Cu3 N3 1.981(3) . ? Cu3 O5 2.350(3) . ? Cu4 O7 1.895(2) 2_655 ? Cu4 O7 1.895(2) . ? Cu4 O10 1.912(2) . ? Cu4 O10 1.912(2) 2_655 ? Cu5 O10 1.914(2) . ? Cu5 N6 1.934(3) . ? Cu5 O9 1.961(2) . ? Cu5 N5 1.992(3) . ? Cu5 O11 2.433(3) . ? Cu6 O7 1.904(2) 2_655 ? Cu6 O8 1.944(2) 2_655 ? Cu6 N8 1.952(3) . ? Cu6 N7 1.971(3) . ? Cl1 O13 1.422(3) . ? Cl1 O12 1.435(3) . ? Cl1 O15 1.436(3) . ? Cl1 O14 1.447(3) . ? Cl2 O17 1.435(3) . ? Cl2 O16 1.435(3) . ? Cl2 O18 1.438(3) . ? Cl2 O19 1.444(3) . ? O1 C7 1.299(4) . ? O2 N2 1.393(4) . ? O3 C14 1.289(4) . ? O3 Cu2 1.926(2) 2_766 ? O4 N4 1.418(3) . ? O4 Cu2 1.940(2) 2_766 ? O5 C15 1.405(5) . ? O5 H5 0.9500 . ? O6 C16 1.429(4) . ? O6 H6 0.9500 . ? O7 N6 1.415(3) . ? O7 Cu6 1.904(2) 2_655 ? O8 C23 1.294(4) . ? O8 Cu6 1.944(2) 2_655 ? O9 C30 1.299(4) . ? O10 N8 1.395(3) . ? O11 C31 1.422(5) . ? O11 H11A 0.9500 . ? O20 C32 1.417(5) . ? O20 H20A 0.8400 . ? N1 C1 1.459(4) . ? N1 H1A 0.9200 . ? N1 H1B 0.9200 . ? N2 C7 1.306(4) . ? N3 C8 1.446(4) . ? N3 H3A 0.9200 . ? N3 H3B 0.9200 . ? N4 C14 1.307(4) . ? N5 C17 1.450(4) . ? N5 H5A 0.9200 . ? N5 H5B 0.9200 . ? N6 C23 1.303(4) . ? N7 C24 1.454(4) . ? N7 H7A 0.9200 . ? N7 H7B 0.9200 . ? N8 C30 1.311(4) . ? C1 C2 1.383(5) . ? C1 C6 1.399(5) . ? C2 C3 1.386(5) . ? C2 H2 0.9500 . ? C3 C4 1.383(5) . ? C3 H3 0.9500 . ? C4 C5 1.375(5) . ? C4 H4 0.9500 . ? C5 C6 1.400(5) . ? C5 H1 0.9500 . ? C6 C7 1.484(5) . ? C8 C9 1.381(5) . ? C8 C13 1.415(5) . ? C9 C10 1.392(5) . ? C9 H9 0.9500 . ? C10 C11 1.370(5) . ? C10 H10 0.9500 . ? C11 C12 1.389(5) . ? C11 H11 0.9500 . ? C12 C13 1.390(5) . ? C12 H12 0.9500 . ? C13 C14 1.484(4) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.382(5) . ? C17 C22 1.410(5) . ? C18 C19 1.381(5) . ? C18 H18 0.9500 . ? C19 C20 1.390(5) . ? C19 H19 0.9500 . ? C20 C21 1.380(5) . ? C20 H20 0.9500 . ? C21 C22 1.387(5) . ? C21 H21 0.9500 . ? C22 C23 1.495(4) . ? C24 C25 1.393(5) . ? C24 C29 1.402(5) . ? C25 C26 1.382(5) . ? C25 H25 0.9500 . ? C26 C27 1.380(5) . ? C26 H26 0.9500 . ? C27 C28 1.385(5) . ? C27 H27 0.9500 . ? C28 C29 1.397(5) . ? C28 H28 0.9500 . ? C29 C30 1.492(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.00(15) . 2_766 ? O2 Cu1 O4 88.42(9) . . ? O2 Cu1 O4 91.58(9) 2_766 . ? O2 Cu1 O4 91.58(9) . 2_766 ? O2 Cu1 O4 88.42(9) 2_766 2_766 ? O4 Cu1 O4 179.998(1) . 2_766 ? O3 Cu2 O4 81.95(9) 2_766 2_766 ? O3 Cu2 N2 161.48(12) 2_766 . ? O4 Cu2 N2 89.90(10) 2_766 . ? O3 Cu2 N1 99.15(10) 2_766 . ? O4 Cu2 N1 175.59(11) 2_766 . ? N2 Cu2 N1 87.81(11) . . ? O3 Cu2 O6 95.95(10) 2_766 . ? O4 Cu2 O6 96.91(9) 2_766 . ? N2 Cu2 O6 101.54(11) . . ? N1 Cu2 O6 87.24(10) . . ? O2 Cu3 N4 88.99(10) . . ? O2 Cu3 O1 80.69(9) . . ? N4 Cu3 O1 164.19(11) . . ? O2 Cu3 N3 178.11(11) . . ? N4 Cu3 N3 89.13(11) . . ? O1 Cu3 N3 101.12(10) . . ? O2 Cu3 O5 90.97(10) . . ? N4 Cu3 O5 101.56(11) . . ? O1 Cu3 O5 90.63(10) . . ? N3 Cu3 O5 89.54(11) . . ? O7 Cu4 O7 180.0 2_655 . ? O7 Cu4 O10 88.89(9) 2_655 . ? O7 Cu4 O10 91.11(9) . . ? O7 Cu4 O10 91.11(9) 2_655 2_655 ? O7 Cu4 O10 88.89(9) . 2_655 ? O10 Cu4 O10 180.0 . 2_655 ? O10 Cu5 N6 89.80(10) . . ? O10 Cu5 O9 80.46(9) . . ? N6 Cu5 O9 169.62(10) . . ? O10 Cu5 N5 171.93(12) . . ? N6 Cu5 N5 89.33(12) . . ? O9 Cu5 N5 100.82(11) . . ? O10 Cu5 O11 107.41(10) . . ? N6 Cu5 O11 91.81(11) . . ? O9 Cu5 O11 87.71(10) . . ? N5 Cu5 O11 80.64(11) . . ? O7 Cu6 O8 81.66(9) 2_655 2_655 ? O7 Cu6 N8 90.38(10) 2_655 . ? O8 Cu6 N8 171.15(11) 2_655 . ? O7 Cu6 N7 163.30(12) 2_655 . ? O8 Cu6 N7 98.43(11) 2_655 . ? N8 Cu6 N7 90.31(12) . . ? O13 Cl1 O12 110.13(18) . . ? O13 Cl1 O15 110.24(18) . . ? O12 Cl1 O15 109.55(18) . . ? O13 Cl1 O14 110.13(17) . . ? O12 Cl1 O14 108.44(16) . . ? O15 Cl1 O14 108.32(18) . . ? O17 Cl2 O16 110.66(17) . . ? O17 Cl2 O18 109.19(17) . . ? O16 Cl2 O18 109.36(17) . . ? O17 Cl2 O19 109.69(16) . . ? O16 Cl2 O19 109.01(18) . . ? O18 Cl2 O19 108.90(16) . . ? C7 O1 Cu3 111.1(2) . . ? N2 O2 Cu1 120.90(18) . . ? N2 O2 Cu3 114.71(17) . . ? Cu1 O2 Cu3 120.86(12) . . ? C14 O3 Cu2 111.5(2) . 2_766 ? N4 O4 Cu1 116.47(18) . . ? N4 O4 Cu2 111.98(17) . 2_766 ? Cu1 O4 Cu2 114.71(11) . 2_766 ? C15 O5 Cu3 128.0(3) . . ? C15 O5 H5 116.0 . . ? Cu3 O5 H5 116.0 . . ? C16 O6 Cu2 111.0(2) . . ? C16 O6 H6 124.5 . . ? Cu2 O6 H6 124.5 . . ? N6 O7 Cu4 118.70(19) . . ? N6 O7 Cu6 112.49(18) . 2_655 ? Cu4 O7 Cu6 116.50(11) . 2_655 ? C23 O8 Cu6 110.8(2) . 2_655 ? C30 O9 Cu5 111.6(2) . . ? N8 O10 Cu4 119.45(17) . . ? N8 O10 Cu5 114.13(17) . . ? Cu4 O10 Cu5 116.94(12) . . ? C31 O11 Cu5 120.9(2) . . ? C31 O11 H11A 119.5 . . ? Cu5 O11 H11A 119.5 . . ? C32 O20 H20A 109.5 . . ? C1 N1 Cu2 115.7(2) . . ? C1 N1 H1A 108.4 . . ? Cu2 N1 H1A 108.4 . . ? C1 N1 H1B 108.4 . . ? Cu2 N1 H1B 108.4 . . ? H1A N1 H1B 107.4 . . ? C7 N2 O2 112.4(3) . . ? C7 N2 Cu2 131.8(2) . . ? O2 N2 Cu2 115.81(18) . . ? C8 N3 Cu3 119.1(2) . . ? C8 N3 H3A 107.6 . . ? Cu3 N3 H3A 107.6 . . ? C8 N3 H3B 107.6 . . ? Cu3 N3 H3B 107.6 . . ? H3A N3 H3B 107.0 . . ? C14 N4 O4 111.3(2) . . ? C14 N4 Cu3 131.3(2) . . ? O4 N4 Cu3 116.28(19) . . ? C17 N5 Cu5 120.3(2) . . ? C17 N5 H5A 107.2 . . ? Cu5 N5 H5A 107.2 . . ? C17 N5 H5B 107.2 . . ? Cu5 N5 H5B 107.2 . . ? H5A N5 H5B 106.9 . . ? C23 N6 O7 111.5(3) . . ? C23 N6 Cu5 133.6(2) . . ? O7 N6 Cu5 114.95(19) . . ? C24 N7 Cu6 121.8(2) . . ? C24 N7 H7A 106.9 . . ? Cu6 N7 H7A 106.9 . . ? C24 N7 H7B 106.9 . . ? Cu6 N7 H7B 106.9 . . ? H7A N7 H7B 106.7 . . ? C30 N8 O10 111.7(3) . . ? C30 N8 Cu6 130.9(2) . . ? O10 N8 Cu6 116.26(18) . . ? C2 C1 C6 120.4(3) . . ? C2 C1 N1 118.3(3) . . ? C6 C1 N1 121.3(3) . . ? C1 C2 C3 120.8(3) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C5 C4 C3 119.5(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 122.1(3) . . ? C4 C5 H1 118.9 . . ? C6 C5 H1 118.9 . . ? C5 C6 C1 117.5(3) . . ? C5 C6 C7 118.2(3) . . ? C1 C6 C7 124.2(3) . . ? O1 C7 N2 121.1(3) . . ? O1 C7 C6 121.1(3) . . ? N2 C7 C6 117.8(3) . . ? C9 C8 C13 119.9(3) . . ? C9 C8 N3 118.5(3) . . ? C13 C8 N3 121.6(3) . . ? C8 C9 C10 120.8(3) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C11 C10 C9 120.0(3) . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 C12 119.6(3) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 121.9(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C12 C13 C8 117.7(3) . . ? C12 C13 C14 116.8(3) . . ? C8 C13 C14 125.2(3) . . ? O3 C14 N4 123.0(3) . . ? O3 C14 C13 117.4(3) . . ? N4 C14 C13 119.3(3) . . ? O5 C15 H15A 109.5 . . ? O5 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O5 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O6 C16 H16A 109.5 . . ? O6 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O6 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 119.9(3) . . ? C18 C17 N5 118.0(3) . . ? C22 C17 N5 122.0(3) . . ? C19 C18 C17 121.4(3) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 119.2(3) . . ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 . . ? C21 C20 C19 119.7(3) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 122.0(3) . . ? C20 C21 H21 119.0 . . ? C22 C21 H21 119.0 . . ? C21 C22 C17 117.8(3) . . ? C21 C22 C23 117.3(3) . . ? C17 C22 C23 124.9(3) . . ? O8 C23 N6 122.0(3) . . ? O8 C23 C22 119.6(3) . . ? N6 C23 C22 118.4(3) . . ? C25 C24 C29 120.0(3) . . ? C25 C24 N7 117.4(3) . . ? C29 C24 N7 122.6(3) . . ? C26 C25 C24 121.1(3) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C27 C26 C25 119.6(3) . . ? C27 C26 H26 120.2 . . ? C25 C26 H26 120.2 . . ? C26 C27 C28 119.5(3) . . ? C26 C27 H27 120.3 . . ? C28 C27 H27 120.3 . . ? C27 C28 C29 122.2(3) . . ? C27 C28 H28 118.9 . . ? C29 C28 H28 118.9 . . ? C28 C29 C24 117.6(3) . . ? C28 C29 C30 117.0(3) . . ? C24 C29 C30 125.3(3) . . ? O9 C30 N8 121.0(3) . . ? O9 C30 C29 118.8(3) . . ? N8 C30 C29 120.2(3) . . ? O11 C31 H31A 109.5 . . ? O11 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O11 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? O20 C32 H32A 109.5 . . ? O20 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O20 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.724 _refine_diff_density_min -0.814 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 936489'