# Electronic Supplementary Material (ESI) for Chemical Science # 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_sx258cc _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H55 Cu6 F N12 O5' _chemical_formula_weight 1112.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 9.9429(8) _cell_length_b 22.7410(16) _cell_length_c 10.5329(7) _cell_angle_alpha 90.00 _cell_angle_beta 111.939(7) _cell_angle_gamma 90.00 _cell_volume 2209.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4072 _cell_measurement_theta_min 3.3949 _cell_measurement_theta_max 25.0317 _exptl_crystal_description needle _exptl_crystal_colour green _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.672 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1132 _exptl_absorpt_coefficient_mu 2.893 _exptl_absorpt_correction_T_min 0.81937 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0267 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 69821 _diffrn_reflns_av_R_equivalents 0.1580 _diffrn_reflns_av_sigmaI/netI 0.0674 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 25.09 _reflns_number_total 4017 _reflns_number_gt 2368 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4017 _refine_ls_number_parameters 293 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1089 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 0.23349(7) 0.18693(3) -0.66434(7) 0.0477(2) Uani 1 1 d . . . Cu2 Cu 0.02780(11) 0.2500 -0.92748(10) 0.0469(3) Uani 1 2 d S . . Cu3 Cu 0.46863(8) 0.18772(3) -0.82775(7) 0.0520(3) Uani 1 1 d . . . Cu4 Cu 0.23939(11) 0.2500 -1.07619(10) 0.0552(3) Uani 1 2 d S . . F1 F 0.2817(4) 0.2500 -0.8275(4) 0.0499(12) Uani 1 2 d S . . O2 O 0.0315(7) 0.2500 -1.1107(6) 0.0568(16) Uani 1 2 d SD . . H2 H 0.008(14) 0.219(3) -1.160(11) 0.085 Uiso 0.50 1 d PD . . N1 N 0.0928(5) 0.1360(2) -0.8029(5) 0.0536(13) Uani 1 1 d . . . N2 N 0.0037(5) 0.1651(2) -0.9173(5) 0.0498(13) Uani 1 1 d . . . C3 C -0.0874(7) 0.1255(3) -1.0014(7) 0.0602(18) Uani 1 1 d . . . C4 C -0.0552(8) 0.0711(3) -0.9404(7) 0.070(2) Uani 1 1 d . . . H4 H -0.1000 0.0356 -0.9761 0.085 Uiso 1 1 calc R . . C5 C 0.0563(7) 0.0795(3) -0.8162(7) 0.0602(18) Uani 1 1 d . . . C6 C -0.2024(7) 0.1429(3) -1.1361(6) 0.081(2) Uani 1 1 d . . . H6A H -0.2964 0.1365 -1.1327 0.121 Uiso 1 1 calc R . . H6B H -0.1925 0.1195 -1.2080 0.121 Uiso 1 1 calc R . . H6C H -0.1915 0.1837 -1.1533 0.121 Uiso 1 1 calc R . . C7 C 0.1296(8) 0.0349(3) -0.7077(8) 0.095(3) Uani 1 1 d . . . H7A H 0.2325 0.0412 -0.6732 0.143 Uiso 1 1 calc R . . H7B H 0.1083 -0.0039 -0.7460 0.143 Uiso 1 1 calc R . . H7C H 0.0950 0.0388 -0.6343 0.143 Uiso 1 1 calc R . . N11 N 0.3455(5) 0.1362(2) -0.9779(5) 0.0583(14) Uani 1 1 d . . . N12 N 0.2541(6) 0.1648(2) -1.0914(5) 0.0606(14) Uani 1 1 d . . . C13 C 0.1790(7) 0.1261(3) -1.1847(7) 0.0651(19) Uani 1 1 d . . . C14 C 0.2214(8) 0.0704(3) -1.1340(7) 0.073(2) Uani 1 1 d . . . H14 H 0.1880 0.0348 -1.1782 0.088 Uiso 1 1 calc R . . C15 C 0.3242(7) 0.0784(3) -1.0034(7) 0.0608(17) Uani 1 1 d . . . C16 C 0.0707(8) 0.1454(4) -1.3213(7) 0.096(3) Uani 1 1 d . . . H16A H -0.0198 0.1545 -1.3127 0.145 Uiso 1 1 calc R . . H16B H 0.0563 0.1143 -1.3869 0.145 Uiso 1 1 calc R . . H16C H 0.1064 0.1797 -1.3516 0.145 Uiso 1 1 calc R . . C17 C 0.4019(8) 0.0327(3) -0.9010(7) 0.090(2) Uani 1 1 d . . . H17A H 0.5046 0.0371 -0.8763 0.135 Uiso 1 1 calc R . . H17B H 0.3727 -0.0057 -0.9397 0.135 Uiso 1 1 calc R . . H17C H 0.3785 0.0370 -0.8209 0.135 Uiso 1 1 calc R . . N21 N 0.4042(5) 0.1361(2) -0.6034(5) 0.0527(13) Uani 1 1 d . . . N22 N 0.4967(5) 0.1361(2) -0.6731(5) 0.0522(13) Uani 1 1 d . . . C23 C 0.6140(7) 0.1023(3) -0.6045(7) 0.0577(17) Uani 1 1 d . . . C24 C 0.5941(7) 0.0799(3) -0.4909(7) 0.0659(19) Uani 1 1 d . . . H24 H 0.6569 0.0549 -0.4256 0.079 Uiso 1 1 calc R . . C25 C 0.4644(7) 0.1013(3) -0.4921(6) 0.0590(18) Uani 1 1 d . . . C26 C 0.7345(7) 0.0947(3) -0.6544(7) 0.084(2) Uani 1 1 d . . . H26A H 0.7272 0.1242 -0.7219 0.126 Uiso 1 1 calc R . . H26B H 0.7284 0.0564 -0.6944 0.126 Uiso 1 1 calc R . . H26C H 0.8256 0.0987 -0.5791 0.126 Uiso 1 1 calc R . . C27 C 0.3945(8) 0.0921(3) -0.3917(7) 0.083(2) Uani 1 1 d . . . H27A H 0.4512 0.1108 -0.3068 0.124 Uiso 1 1 calc R . . H27B H 0.3881 0.0507 -0.3769 0.124 Uiso 1 1 calc R . . H27C H 0.2989 0.1088 -0.4265 0.124 Uiso 1 1 calc R . . O31 O 0.0808(5) 0.2500 -0.7255(5) 0.0441(13) Uani 1 2 d S . . C31 C -0.0345(9) 0.2500 -0.6763(9) 0.065(3) Uani 1 2 d S . . H31A H 0.0034 0.2415 -0.5800 0.097 Uiso 0.50 1 calc PR . . H31B H -0.1043 0.2206 -0.7239 0.097 Uiso 0.50 1 calc PR . . H31C H -0.0802 0.2879 -0.6918 0.097 Uiso 0.50 1 calc PR . . O32 O 0.4512(6) 0.2500 -0.9688(5) 0.0559(16) Uani 1 2 d S . . C32 C 0.5505(10) 0.2500 -1.0355(9) 0.084(3) Uani 1 2 d S . . H32A H 0.5255 0.2806 -1.1031 0.126 Uiso 0.50 1 calc PR . . H32B H 0.5472 0.2127 -1.0791 0.126 Uiso 0.50 1 calc PR . . H32C H 0.6466 0.2567 -0.9696 0.126 Uiso 0.50 1 calc PR . . O33 O 0.3156(6) 0.2500 -0.5375(5) 0.0567(16) Uani 1 2 d S . . C33 C 0.4271(13) 0.2500 -0.4066(11) 0.113(4) Uani 1 2 d S . . H33A H 0.4671 0.2888 -0.3855 0.170 Uiso 0.50 1 calc PR . . H33B H 0.5018 0.2230 -0.4057 0.170 Uiso 0.50 1 calc PR . . H33C H 0.3884 0.2381 -0.3397 0.170 Uiso 0.50 1 calc PR . . O34 O 0.5983(6) 0.2500 -0.7213(5) 0.0576(16) Uani 1 2 d S . . C34 C 0.6699(9) 0.2500 -0.5740(8) 0.065(3) Uani 1 2 d S . . H34A H 0.6058 0.2340 -0.5336 0.098 Uiso 0.50 1 calc PR . . H34B H 0.6953 0.2896 -0.5423 0.098 Uiso 0.50 1 calc PR . . H34C H 0.7561 0.2264 -0.5482 0.098 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 0.0474(5) 0.0429(5) 0.0473(4) 0.0019(3) 0.0112(4) 0.0025(3) Cu2 0.0494(6) 0.0395(6) 0.0455(6) 0.000 0.0105(5) 0.000 Cu3 0.0507(5) 0.0537(5) 0.0482(5) -0.0010(4) 0.0146(4) 0.0038(4) Cu4 0.0564(7) 0.0584(8) 0.0461(6) 0.000 0.0136(5) 0.000 F1 0.045(3) 0.055(3) 0.049(3) 0.000 0.016(2) 0.000 O2 0.060(4) 0.063(5) 0.043(4) 0.000 0.013(3) 0.000 N1 0.055(3) 0.039(3) 0.061(3) 0.003(3) 0.016(3) 0.000(3) N2 0.051(3) 0.044(3) 0.051(3) 0.001(3) 0.014(3) -0.001(3) C3 0.061(4) 0.050(4) 0.064(4) -0.011(4) 0.017(4) 0.002(4) C4 0.076(5) 0.045(5) 0.080(5) -0.008(4) 0.017(4) -0.008(4) C5 0.063(4) 0.041(4) 0.070(5) 0.002(3) 0.017(4) -0.001(3) C6 0.070(5) 0.080(6) 0.070(5) -0.010(4) 0.000(4) -0.007(4) C7 0.086(6) 0.040(4) 0.126(7) 0.019(4) 0.002(5) 0.006(4) N11 0.064(4) 0.056(4) 0.052(3) -0.002(3) 0.017(3) 0.004(3) N12 0.057(3) 0.068(4) 0.051(3) -0.013(3) 0.013(3) 0.000(3) C13 0.066(5) 0.072(5) 0.059(5) -0.012(4) 0.026(4) 0.005(4) C14 0.078(5) 0.074(6) 0.066(5) -0.021(4) 0.025(4) -0.009(4) C15 0.064(4) 0.056(5) 0.063(4) -0.007(4) 0.026(4) 0.004(4) C16 0.082(6) 0.123(8) 0.063(5) -0.023(5) 0.003(4) 0.003(5) C17 0.103(6) 0.065(5) 0.082(5) -0.009(4) 0.012(5) 0.002(5) N21 0.055(3) 0.046(3) 0.050(3) 0.001(3) 0.012(3) -0.001(3) N22 0.051(3) 0.048(3) 0.052(3) -0.004(2) 0.013(3) 0.006(3) C23 0.059(4) 0.049(4) 0.057(4) -0.002(3) 0.012(4) 0.016(3) C24 0.058(5) 0.063(5) 0.058(4) 0.009(4) 0.000(4) 0.016(4) C25 0.067(5) 0.045(4) 0.054(4) 0.010(3) 0.011(4) 0.007(3) C26 0.071(5) 0.079(6) 0.101(6) -0.006(5) 0.029(5) 0.018(4) C27 0.088(6) 0.086(6) 0.072(5) 0.029(4) 0.028(4) 0.012(5) O31 0.041(3) 0.043(3) 0.046(3) 0.000 0.013(3) 0.000 C31 0.060(6) 0.072(7) 0.069(6) 0.000 0.032(5) 0.000 O32 0.061(4) 0.066(4) 0.046(3) 0.000 0.026(3) 0.000 C32 0.066(7) 0.125(10) 0.071(7) 0.000 0.038(6) 0.000 O33 0.059(4) 0.048(4) 0.050(4) 0.000 0.004(3) 0.000 C33 0.134(11) 0.089(9) 0.074(8) 0.000 -0.011(8) 0.000 O34 0.047(4) 0.067(4) 0.047(3) 0.000 0.003(3) 0.000 C34 0.051(6) 0.072(7) 0.064(6) 0.000 0.011(5) 0.000 _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O33 1.922(4) . ? Cu1 N21 1.954(5) . ? Cu1 N1 1.976(5) . ? Cu1 O31 2.011(3) . ? Cu1 F1 2.420(3) . ? Cu1 Cu1 2.8685(14) 4_565 ? Cu2 O2 1.944(6) . ? Cu2 N2 1.954(5) . ? Cu2 N2 1.954(5) 4_565 ? Cu2 O31 1.991(5) . ? Cu2 F1 2.344(4) . ? Cu2 Cu4 3.0564(15) . ? Cu3 N22 1.942(5) . ? Cu3 O34 1.961(4) . ? Cu3 N11 1.982(5) . ? Cu3 O32 2.013(4) . ? Cu3 F1 2.338(3) . ? Cu3 Cu3 2.8327(15) 4_565 ? Cu4 N12 1.953(5) . ? Cu4 N12 1.953(5) 4_565 ? Cu4 O2 1.961(7) . ? Cu4 O32 1.984(6) . ? F1 Cu3 2.338(3) 4_565 ? F1 Cu1 2.420(3) 4_565 ? O2 H2 0.848(10) . ? N1 C5 1.328(7) . ? N1 N2 1.370(6) . ? N2 C3 1.348(7) . ? C3 C4 1.375(9) . ? C3 C6 1.504(8) . ? C4 C5 1.376(8) . ? C4 H4 0.9300 . ? C5 C7 1.498(8) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? N11 C15 1.342(8) . ? N11 N12 1.366(6) . ? N12 C13 1.324(8) . ? C13 C14 1.377(9) . ? C13 C16 1.505(9) . ? C14 C15 1.385(8) . ? C14 H14 0.9300 . ? C15 C17 1.491(9) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? N21 C25 1.354(7) . ? N21 N22 1.375(6) . ? N22 C23 1.358(7) . ? C23 C24 1.380(8) . ? C23 C26 1.487(9) . ? C24 C25 1.374(8) . ? C24 H24 0.9300 . ? C25 C27 1.481(9) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? O31 C31 1.424(9) . ? O31 Cu1 2.011(3) 4_565 ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? O32 C32 1.410(9) . ? O32 Cu3 2.013(4) 4_565 ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? O33 C33 1.409(11) . ? O33 Cu1 1.922(4) 4_565 ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? O34 C34 1.445(9) . ? O34 Cu3 1.961(4) 4_565 ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O33 Cu1 N21 97.0(2) . . ? O33 Cu1 N1 162.0(2) . . ? N21 Cu1 N1 100.6(2) . . ? O33 Cu1 O31 76.37(18) . . ? N21 Cu1 O31 170.57(18) . . ? N1 Cu1 O31 86.58(18) . . ? O33 Cu1 F1 84.61(16) . . ? N21 Cu1 F1 101.89(17) . . ? N1 Cu1 F1 95.55(16) . . ? O31 Cu1 F1 71.08(15) . . ? O33 Cu1 Cu1 41.73(12) . 4_565 ? N21 Cu1 Cu1 126.31(14) . 4_565 ? N1 Cu1 Cu1 125.92(15) . 4_565 ? O31 Cu1 Cu1 44.51(10) . 4_565 ? F1 Cu1 Cu1 53.65(6) . 4_565 ? O2 Cu2 N2 95.90(14) . . ? O2 Cu2 N2 95.90(14) . 4_565 ? N2 Cu2 N2 162.5(3) . 4_565 ? O2 Cu2 O31 164.8(2) . . ? N2 Cu2 O31 86.00(14) . . ? N2 Cu2 O31 86.00(14) 4_565 . ? O2 Cu2 F1 91.7(2) . . ? N2 Cu2 F1 96.26(14) . . ? N2 Cu2 F1 96.26(14) 4_565 . ? O31 Cu2 F1 73.09(17) . . ? O2 Cu2 Cu4 38.68(19) . . ? N2 Cu2 Cu4 98.64(14) . . ? N2 Cu2 Cu4 98.64(14) 4_565 . ? O31 Cu2 Cu4 126.10(15) . . ? F1 Cu2 Cu4 53.02(10) . . ? N22 Cu3 O34 95.68(19) . . ? N22 Cu3 N11 99.5(2) . . ? O34 Cu3 N11 164.1(2) . . ? N22 Cu3 O32 172.10(18) . . ? O34 Cu3 O32 76.75(17) . . ? N11 Cu3 O32 88.3(2) . . ? N22 Cu3 F1 103.33(17) . . ? O34 Cu3 F1 85.11(16) . . ? N11 Cu3 F1 96.00(17) . . ? O32 Cu3 F1 74.06(16) . . ? N22 Cu3 Cu3 127.20(14) . 4_565 ? O34 Cu3 Cu3 43.76(11) . 4_565 ? N11 Cu3 Cu3 126.24(16) . 4_565 ? O32 Cu3 Cu3 45.27(10) . 4_565 ? F1 Cu3 Cu3 52.71(6) . 4_565 ? N12 Cu4 N12 165.0(3) . 4_565 ? N12 Cu4 O2 95.23(15) . . ? N12 Cu4 O2 95.23(15) 4_565 . ? N12 Cu4 O32 87.16(15) . . ? N12 Cu4 O32 87.16(15) 4_565 . ? O2 Cu4 O32 158.0(2) . . ? N12 Cu4 Cu2 97.42(15) . . ? N12 Cu4 Cu2 97.42(15) 4_565 . ? O2 Cu4 Cu2 38.28(17) . . ? O32 Cu4 Cu2 119.68(15) . . ? Cu3 F1 Cu3 74.58(13) 4_565 . ? Cu3 F1 Cu2 136.28(11) 4_565 . ? Cu3 F1 Cu2 136.28(11) . . ? Cu3 F1 Cu1 136.76(18) 4_565 . ? Cu3 F1 Cu1 90.59(8) . . ? Cu2 F1 Cu1 81.57(12) . . ? Cu3 F1 Cu1 90.59(8) 4_565 4_565 ? Cu3 F1 Cu1 136.76(18) . 4_565 ? Cu2 F1 Cu1 81.57(12) . 4_565 ? Cu1 F1 Cu1 72.70(12) . 4_565 ? Cu2 O2 Cu4 103.0(3) . . ? Cu2 O2 H2 121(9) . . ? Cu4 O2 H2 98(9) . . ? C5 N1 N2 108.2(5) . . ? C5 N1 Cu1 137.4(4) . . ? N2 N1 Cu1 114.4(4) . . ? C3 N2 N1 108.1(5) . . ? C3 N2 Cu2 133.7(4) . . ? N1 N2 Cu2 118.2(4) . . ? N2 C3 C4 108.2(6) . . ? N2 C3 C6 122.1(6) . . ? C4 C3 C6 129.7(6) . . ? C5 C4 C3 106.5(6) . . ? C5 C4 H4 126.8 . . ? C3 C4 H4 126.8 . . ? N1 C5 C4 109.0(6) . . ? N1 C5 C7 122.6(6) . . ? C4 C5 C7 128.4(6) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C15 N11 N12 106.8(5) . . ? C15 N11 Cu3 138.0(5) . . ? N12 N11 Cu3 115.3(4) . . ? C13 N12 N11 109.8(6) . . ? C13 N12 Cu4 133.0(5) . . ? N11 N12 Cu4 116.5(4) . . ? N12 C13 C14 108.5(6) . . ? N12 C13 C16 121.2(7) . . ? C14 C13 C16 130.2(7) . . ? C13 C14 C15 105.6(6) . . ? C13 C14 H14 127.2 . . ? C15 C14 H14 127.2 . . ? N11 C15 C14 109.3(6) . . ? N11 C15 C17 122.6(6) . . ? C14 C15 C17 128.1(7) . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C25 N21 N22 107.2(5) . . ? C25 N21 Cu1 132.7(5) . . ? N22 N21 Cu1 119.8(4) . . ? C23 N22 N21 109.2(5) . . ? C23 N22 Cu3 127.9(5) . . ? N21 N22 Cu3 122.2(4) . . ? N22 C23 C24 107.3(6) . . ? N22 C23 C26 121.5(6) . . ? C24 C23 C26 131.3(6) . . ? C25 C24 C23 107.5(6) . . ? C25 C24 H24 126.3 . . ? C23 C24 H24 126.3 . . ? N21 C25 C24 108.9(6) . . ? N21 C25 C27 121.8(6) . . ? C24 C25 C27 129.2(6) . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C31 O31 Cu2 117.5(5) . . ? C31 O31 Cu1 119.8(3) . 4_565 ? Cu2 O31 Cu1 102.08(19) . 4_565 ? C31 O31 Cu1 119.8(3) . . ? Cu2 O31 Cu1 102.08(19) . . ? Cu1 O31 Cu1 91.0(2) 4_565 . ? O31 C31 H31A 109.5 . . ? O31 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? O31 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C32 O32 Cu4 120.5(5) . . ? C32 O32 Cu3 119.0(3) . . ? Cu4 O32 Cu3 101.6(2) . . ? C32 O32 Cu3 119.0(3) . 4_565 ? Cu4 O32 Cu3 101.6(2) . 4_565 ? Cu3 O32 Cu3 89.5(2) . 4_565 ? O32 C32 H32A 109.5 . . ? O32 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? O32 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C33 O33 Cu1 130.87(17) . . ? C33 O33 Cu1 130.87(16) . 4_565 ? Cu1 O33 Cu1 96.5(2) . 4_565 ? O33 C33 H33A 109.5 . . ? O33 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? O33 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C34 O34 Cu3 124.7(3) . . ? C34 O34 Cu3 124.7(3) . 4_565 ? Cu3 O34 Cu3 92.5(2) . 4_565 ? O34 C34 H34A 109.5 . . ? O34 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? O34 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Cu2 Cu4 N12 -89.04(15) . . . . ? N2 Cu2 Cu4 N12 -0.4(2) . . . . ? N2 Cu2 Cu4 N12 -177.7(2) 4_565 . . . ? O31 Cu2 Cu4 N12 90.96(16) . . . . ? F1 Cu2 Cu4 N12 90.96(16) . . . . ? O2 Cu2 Cu4 N12 89.04(16) . . . 4_565 ? N2 Cu2 Cu4 N12 177.7(2) . . . 4_565 ? N2 Cu2 Cu4 N12 0.4(2) 4_565 . . 4_565 ? O31 Cu2 Cu4 N12 -90.96(16) . . . 4_565 ? F1 Cu2 Cu4 N12 -90.96(16) . . . 4_565 ? N2 Cu2 Cu4 O2 88.65(14) . . . . ? N2 Cu2 Cu4 O2 -88.65(14) 4_565 . . . ? O31 Cu2 Cu4 O2 180.000(3) . . . . ? F1 Cu2 Cu4 O2 180.000(3) . . . . ? O2 Cu2 Cu4 O32 180.000(1) . . . . ? N2 Cu2 Cu4 O32 -91.35(14) . . . . ? N2 Cu2 Cu4 O32 91.35(14) 4_565 . . . ? O31 Cu2 Cu4 O32 0.000(2) . . . . ? F1 Cu2 Cu4 O32 0.000(2) . . . . ? N22 Cu3 F1 Cu3 126.91(16) . . . 4_565 ? O34 Cu3 F1 Cu3 32.22(16) . . . 4_565 ? N11 Cu3 F1 Cu3 -131.84(16) . . . 4_565 ? O32 Cu3 F1 Cu3 -45.38(14) . . . 4_565 ? N22 Cu3 F1 Cu2 -90.3(3) . . . . ? O34 Cu3 F1 Cu2 175.0(3) . . . . ? N11 Cu3 F1 Cu2 10.9(3) . . . . ? O32 Cu3 F1 Cu2 97.4(3) . . . . ? Cu3 Cu3 F1 Cu2 142.8(3) 4_565 . . . ? N22 Cu3 F1 Cu1 -11.93(18) . . . . ? O34 Cu3 F1 Cu1 -106.63(17) . . . . ? N11 Cu3 F1 Cu1 89.31(18) . . . . ? O32 Cu3 F1 Cu1 175.78(17) . . . . ? Cu3 Cu3 F1 Cu1 -138.84(15) 4_565 . . . ? N22 Cu3 F1 Cu1 53.0(2) . . . 4_565 ? O34 Cu3 F1 Cu1 -41.7(2) . . . 4_565 ? N11 Cu3 F1 Cu1 154.3(2) . . . 4_565 ? O32 Cu3 F1 Cu1 -119.3(2) . . . 4_565 ? Cu3 Cu3 F1 Cu1 -73.87(15) 4_565 . . 4_565 ? O2 Cu2 F1 Cu3 61.2(2) . . . 4_565 ? N2 Cu2 F1 Cu3 157.4(2) . . . 4_565 ? N2 Cu2 F1 Cu3 -34.9(3) 4_565 . . 4_565 ? O31 Cu2 F1 Cu3 -118.8(2) . . . 4_565 ? Cu4 Cu2 F1 Cu3 61.2(2) . . . 4_565 ? O2 Cu2 F1 Cu3 -61.2(2) . . . . ? N2 Cu2 F1 Cu3 34.9(3) . . . . ? N2 Cu2 F1 Cu3 -157.4(2) 4_565 . . . ? O31 Cu2 F1 Cu3 118.8(2) . . . . ? Cu4 Cu2 F1 Cu3 -61.2(2) . . . . ? O2 Cu2 F1 Cu1 -143.19(5) . . . . ? N2 Cu2 F1 Cu1 -47.06(15) . . . . ? N2 Cu2 F1 Cu1 120.69(15) 4_565 . . . ? O31 Cu2 F1 Cu1 36.81(5) . . . . ? Cu4 Cu2 F1 Cu1 -143.19(5) . . . . ? O2 Cu2 F1 Cu1 143.19(5) . . . 4_565 ? N2 Cu2 F1 Cu1 -120.69(15) . . . 4_565 ? N2 Cu2 F1 Cu1 47.06(15) 4_565 . . 4_565 ? O31 Cu2 F1 Cu1 -36.81(5) . . . 4_565 ? Cu4 Cu2 F1 Cu1 143.19(5) . . . 4_565 ? O33 Cu1 F1 Cu3 41.1(2) . . . 4_565 ? N21 Cu1 F1 Cu3 -55.0(2) . . . 4_565 ? N1 Cu1 F1 Cu3 -157.1(2) . . . 4_565 ? O31 Cu1 F1 Cu3 118.5(2) . . . 4_565 ? Cu1 Cu1 F1 Cu3 71.61(14) 4_565 . . 4_565 ? O33 Cu1 F1 Cu3 108.90(18) . . . . ? N21 Cu1 F1 Cu3 12.84(18) . . . . ? N1 Cu1 F1 Cu3 -89.22(17) . . . . ? O31 Cu1 F1 Cu3 -173.68(16) . . . . ? Cu1 Cu1 F1 Cu3 139.45(15) 4_565 . . . ? O33 Cu1 F1 Cu2 -114.29(16) . . . . ? N21 Cu1 F1 Cu2 149.65(15) . . . . ? N1 Cu1 F1 Cu2 47.59(15) . . . . ? O31 Cu1 F1 Cu2 -36.87(12) . . . . ? Cu1 Cu1 F1 Cu2 -83.74(8) 4_565 . . . ? O33 Cu1 F1 Cu1 -30.55(17) . . . 4_565 ? N21 Cu1 F1 Cu1 -126.61(15) . . . 4_565 ? N1 Cu1 F1 Cu1 131.33(16) . . . 4_565 ? O31 Cu1 F1 Cu1 46.87(13) . . . 4_565 ? N2 Cu2 O2 Cu4 -96.47(14) . . . . ? N2 Cu2 O2 Cu4 96.47(14) 4_565 . . . ? O31 Cu2 O2 Cu4 0.000(5) . . . . ? F1 Cu2 O2 Cu4 0.0 . . . . ? N12 Cu4 O2 Cu2 95.36(15) . . . . ? N12 Cu4 O2 Cu2 -95.36(15) 4_565 . . . ? O32 Cu4 O2 Cu2 0.000(3) . . . . ? O33 Cu1 N1 C5 -126.3(7) . . . . ? N21 Cu1 N1 C5 40.9(7) . . . . ? O31 Cu1 N1 C5 -145.3(7) . . . . ? F1 Cu1 N1 C5 144.1(6) . . . . ? Cu1 Cu1 N1 C5 -167.6(6) 4_565 . . . ? O33 Cu1 N1 N2 51.8(8) . . . . ? N21 Cu1 N1 N2 -141.0(4) . . . . ? O31 Cu1 N1 N2 32.8(4) . . . . ? F1 Cu1 N1 N2 -37.8(4) . . . . ? Cu1 Cu1 N1 N2 10.5(4) 4_565 . . . ? C5 N1 N2 C3 -0.4(7) . . . . ? Cu1 N1 N2 C3 -179.1(4) . . . . ? C5 N1 N2 Cu2 178.9(4) . . . . ? Cu1 N1 N2 Cu2 0.2(5) . . . . ? O2 Cu2 N2 C3 -49.6(6) . . . . ? N2 Cu2 N2 C3 82.6(11) 4_565 . . . ? O31 Cu2 N2 C3 145.6(6) . . . . ? F1 Cu2 N2 C3 -141.9(6) . . . . ? Cu4 Cu2 N2 C3 -88.5(6) . . . . ? O2 Cu2 N2 N1 131.3(4) . . . . ? N2 Cu2 N2 N1 -96.5(10) 4_565 . . . ? O31 Cu2 N2 N1 -33.5(4) . . . . ? F1 Cu2 N2 N1 39.0(4) . . . . ? Cu4 Cu2 N2 N1 92.4(4) . . . . ? N1 N2 C3 C4 -0.3(7) . . . . ? Cu2 N2 C3 C4 -179.5(5) . . . . ? N1 N2 C3 C6 178.8(6) . . . . ? Cu2 N2 C3 C6 -0.4(10) . . . . ? N2 C3 C4 C5 1.0(8) . . . . ? C6 C3 C4 C5 -178.1(7) . . . . ? N2 N1 C5 C4 1.1(7) . . . . ? Cu1 N1 C5 C4 179.2(5) . . . . ? N2 N1 C5 C7 -178.5(6) . . . . ? Cu1 N1 C5 C7 -0.4(11) . . . . ? C3 C4 C5 N1 -1.3(8) . . . . ? C3 C4 C5 C7 178.3(7) . . . . ? N22 Cu3 N11 C15 -27.9(7) . . . . ? O34 Cu3 N11 C15 134.3(8) . . . . ? O32 Cu3 N11 C15 153.7(7) . . . . ? F1 Cu3 N11 C15 -132.5(6) . . . . ? Cu3 Cu3 N11 C15 -179.8(6) 4_565 . . . ? N22 Cu3 N11 N12 152.7(4) . . . . ? O34 Cu3 N11 N12 -45.2(9) . . . . ? O32 Cu3 N11 N12 -25.7(4) . . . . ? F1 Cu3 N11 N12 48.0(4) . . . . ? Cu3 Cu3 N11 N12 0.7(5) 4_565 . . . ? C15 N11 N12 C13 -0.3(7) . . . . ? Cu3 N11 N12 C13 179.3(4) . . . . ? C15 N11 N12 Cu4 171.5(4) . . . . ? Cu3 N11 N12 Cu4 -8.8(5) . . . . ? N12 Cu4 N12 C13 -83.6(14) 4_565 . . . ? O2 Cu4 N12 C13 50.5(6) . . . . ? O32 Cu4 N12 C13 -151.4(6) . . . . ? Cu2 Cu4 N12 C13 89.0(6) . . . . ? N12 Cu4 N12 N11 106.9(11) 4_565 . . . ? O2 Cu4 N12 N11 -119.0(4) . . . . ? O32 Cu4 N12 N11 39.1(4) . . . . ? Cu2 Cu4 N12 N11 -80.5(4) . . . . ? N11 N12 C13 C14 -0.6(8) . . . . ? Cu4 N12 C13 C14 -170.6(5) . . . . ? N11 N12 C13 C16 -179.4(6) . . . . ? Cu4 N12 C13 C16 10.6(10) . . . . ? N12 C13 C14 C15 1.3(8) . . . . ? C16 C13 C14 C15 179.9(7) . . . . ? N12 N11 C15 C14 1.1(7) . . . . ? Cu3 N11 C15 C14 -178.4(5) . . . . ? N12 N11 C15 C17 -178.1(6) . . . . ? Cu3 N11 C15 C17 2.4(11) . . . . ? C13 C14 C15 N11 -1.5(8) . . . . ? C13 C14 C15 C17 177.7(7) . . . . ? O33 Cu1 N21 C25 75.3(6) . . . . ? N1 Cu1 N21 C25 -100.8(6) . . . . ? O31 Cu1 N21 C25 120.2(12) . . . . ? F1 Cu1 N21 C25 161.2(5) . . . . ? Cu1 Cu1 N21 C25 107.8(5) 4_565 . . . ? O33 Cu1 N21 N22 -97.7(4) . . . . ? N1 Cu1 N21 N22 86.3(4) . . . . ? O31 Cu1 N21 N22 -52.7(14) . . . . ? F1 Cu1 N21 N22 -11.7(4) . . . . ? Cu1 Cu1 N21 N22 -65.1(4) 4_565 . . . ? C25 N21 N22 C23 -0.7(6) . . . . ? Cu1 N21 N22 C23 173.8(4) . . . . ? C25 N21 N22 Cu3 -172.0(4) . . . . ? Cu1 N21 N22 Cu3 2.5(6) . . . . ? O34 Cu3 N22 C23 -74.8(5) . . . . ? N11 Cu3 N22 C23 100.4(5) . . . . ? O32 Cu3 N22 C23 -91.3(17) . . . . ? F1 Cu3 N22 C23 -161.1(5) . . . . ? Cu3 Cu3 N22 C23 -108.1(5) 4_565 . . . ? O34 Cu3 N22 N21 94.8(4) . . . . ? N11 Cu3 N22 N21 -90.1(4) . . . . ? O32 Cu3 N22 N21 78.3(17) . . . . ? F1 Cu3 N22 N21 8.5(4) . . . . ? Cu3 Cu3 N22 N21 61.5(5) 4_565 . . . ? N21 N22 C23 C24 0.8(7) . . . . ? Cu3 N22 C23 C24 171.5(4) . . . . ? N21 N22 C23 C26 -179.0(6) . . . . ? Cu3 N22 C23 C26 -8.4(9) . . . . ? N22 C23 C24 C25 -0.6(7) . . . . ? C26 C23 C24 C25 179.2(7) . . . . ? N22 N21 C25 C24 0.3(7) . . . . ? Cu1 N21 C25 C24 -173.2(4) . . . . ? N22 N21 C25 C27 178.9(6) . . . . ? Cu1 N21 C25 C27 5.3(9) . . . . ? C23 C24 C25 N21 0.2(7) . . . . ? C23 C24 C25 C27 -178.2(7) . . . . ? O2 Cu2 O31 C31 180.000(3) . . . . ? N2 Cu2 O31 C31 -82.22(14) . . . . ? N2 Cu2 O31 C31 82.22(14) 4_565 . . . ? F1 Cu2 O31 C31 180.000(2) . . . . ? Cu4 Cu2 O31 C31 180.000(2) . . . . ? O2 Cu2 O31 Cu1 46.82(13) . . . 4_565 ? N2 Cu2 O31 Cu1 144.6(2) . . . 4_565 ? N2 Cu2 O31 Cu1 -50.96(18) 4_565 . . 4_565 ? F1 Cu2 O31 Cu1 46.82(13) . . . 4_565 ? Cu4 Cu2 O31 Cu1 46.82(13) . . . 4_565 ? O2 Cu2 O31 Cu1 -46.82(13) . . . . ? N2 Cu2 O31 Cu1 50.96(18) . . . . ? N2 Cu2 O31 Cu1 -144.6(2) 4_565 . . . ? F1 Cu2 O31 Cu1 -46.82(13) . . . . ? Cu4 Cu2 O31 Cu1 -46.82(13) . . . . ? O33 Cu1 O31 C31 -93.7(5) . . . . ? N21 Cu1 O31 C31 -139.9(11) . . . . ? N1 Cu1 O31 C31 80.3(4) . . . . ? F1 Cu1 O31 C31 177.4(5) . . . . ? Cu1 Cu1 O31 C31 -125.6(5) 4_565 . . . ? O33 Cu1 O31 Cu2 134.5(2) . . . . ? N21 Cu1 O31 Cu2 88.3(12) . . . . ? N1 Cu1 O31 Cu2 -51.46(19) . . . . ? F1 Cu1 O31 Cu2 45.60(14) . . . . ? Cu1 Cu1 O31 Cu2 102.6(2) 4_565 . . . ? O33 Cu1 O31 Cu1 31.9(2) . . . 4_565 ? N21 Cu1 O31 Cu1 -14.3(13) . . . 4_565 ? N1 Cu1 O31 Cu1 -154.0(2) . . . 4_565 ? F1 Cu1 O31 Cu1 -56.97(15) . . . 4_565 ? N12 Cu4 O32 C32 83.08(15) . . . . ? N12 Cu4 O32 C32 -83.08(15) 4_565 . . . ? O2 Cu4 O32 C32 180.000(5) . . . . ? Cu2 Cu4 O32 C32 180.000(4) . . . . ? N12 Cu4 O32 Cu3 -51.00(19) . . . . ? N12 Cu4 O32 Cu3 142.8(2) 4_565 . . . ? O2 Cu4 O32 Cu3 45.92(13) . . . . ? Cu2 Cu4 O32 Cu3 45.92(13) . . . . ? N12 Cu4 O32 Cu3 -142.8(2) . . . 4_565 ? N12 Cu4 O32 Cu3 51.00(19) 4_565 . . 4_565 ? O2 Cu4 O32 Cu3 -45.92(13) . . . 4_565 ? Cu2 Cu4 O32 Cu3 -45.92(13) . . . 4_565 ? N22 Cu3 O32 C32 104.4(15) . . . . ? O34 Cu3 O32 C32 87.5(5) . . . . ? N11 Cu3 O32 C32 -87.1(5) . . . . ? F1 Cu3 O32 C32 176.1(5) . . . . ? Cu3 Cu3 O32 C32 123.3(5) 4_565 . . . ? N22 Cu3 O32 Cu4 -120.6(15) . . . . ? O34 Cu3 O32 Cu4 -137.5(2) . . . . ? N11 Cu3 O32 Cu4 47.86(19) . . . . ? F1 Cu3 O32 Cu4 -48.89(15) . . . . ? Cu3 Cu3 O32 Cu4 -101.7(2) 4_565 . . . ? N22 Cu3 O32 Cu3 -18.9(17) . . . 4_565 ? O34 Cu3 O32 Cu3 -35.8(2) . . . 4_565 ? N11 Cu3 O32 Cu3 149.6(2) . . . 4_565 ? F1 Cu3 O32 Cu3 52.84(16) . . . 4_565 ? N21 Cu1 O33 C33 -26.7(9) . . . . ? N1 Cu1 O33 C33 140.6(9) . . . . ? O31 Cu1 O33 C33 160.2(9) . . . . ? F1 Cu1 O33 C33 -128.0(9) . . . . ? Cu1 Cu1 O33 C33 -166.0(10) 4_565 . . . ? N21 Cu1 O33 Cu1 139.3(2) . . . 4_565 ? N1 Cu1 O33 Cu1 -53.4(8) . . . 4_565 ? O31 Cu1 O33 Cu1 -33.9(2) . . . 4_565 ? F1 Cu1 O33 Cu1 38.0(2) . . . 4_565 ? N22 Cu3 O34 C34 -4.5(5) . . . . ? N11 Cu3 O34 C34 -166.8(7) . . . . ? O32 Cu3 O34 C34 173.2(5) . . . . ? F1 Cu3 O34 C34 98.4(5) . . . . ? Cu3 Cu3 O34 C34 136.3(6) 4_565 . . . ? N22 Cu3 O34 Cu3 -140.8(2) . . . 4_565 ? N11 Cu3 O34 Cu3 56.9(8) . . . 4_565 ? O32 Cu3 O34 Cu3 36.9(2) . . . 4_565 ? F1 Cu3 O34 Cu3 -37.82(19) . . . 4_565 ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.09 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.542 _refine_diff_density_min -0.482 _refine_diff_density_rms 0.090 _database_code_depnum_ccdc_archive 'CCDC 927862' ####################################################################### # # 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_sx304bb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H52 Cl3 Cu6 N13 O6' _chemical_formula_weight 1214.47 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 Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 19.8730(5) _cell_length_b 19.8730(5) _cell_length_c 9.9681(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3409.33(18) _cell_formula_units_Z 3 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 1515 _cell_measurement_theta_min 3.1211 _cell_measurement_theta_max 26.3066 _exptl_crystal_description needle _exptl_crystal_colour violet _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.775 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1842 _exptl_absorpt_coefficient_mu 2.990 _exptl_absorpt_correction_T_min 0.92736 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0267 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5934 _diffrn_reflns_av_R_equivalents 0.0518 _diffrn_reflns_av_sigmaI/netI 0.0528 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 26.36 _reflns_number_total 1550 _reflns_number_gt 1283 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+6.9070P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1550 _refine_ls_number_parameters 108 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0356 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _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 0.95650(2) 0.82287(2) -0.00366(4) 0.01204(15) Uani 1 1 d . . . O1 O 1.05274(13) 0.86713(13) 0.0970(2) 0.0130(5) Uani 1 1 d D . . H1 H 1.047(2) 0.875(2) 0.1780(15) 0.019 Uiso 1 1 d D . . N1 N 0.89029(15) 0.79236(15) 0.1556(3) 0.0125(6) Uani 1 1 d . . . N2 N 0.83666(15) 0.81685(15) 0.1629(3) 0.0123(6) Uani 1 1 d . . . C3 C 0.79717(19) 0.79043(19) 0.2789(3) 0.0150(7) Uani 1 1 d . . . C4 C 0.8252(2) 0.7479(2) 0.3460(4) 0.0181(8) Uani 1 1 d . . . H4 H 0.8076 0.7219 0.4296 0.022 Uiso 1 1 calc R . . C5 C 0.88396(19) 0.75104(19) 0.2662(3) 0.0149(8) Uani 1 1 d . . . C6 C 0.7352(2) 0.8077(2) 0.3205(4) 0.0212(8) Uani 1 1 d . . . H6A H 0.7558 0.8487 0.3887 0.032 Uiso 1 1 calc R . . H6B H 0.6911 0.7607 0.3577 0.032 Uiso 1 1 calc R . . H6C H 0.7180 0.8251 0.2424 0.032 Uiso 1 1 calc R . . C7 C 0.9345(2) 0.7162(2) 0.2900(4) 0.0186(8) Uani 1 1 d . . . H7A H 0.9562 0.7117 0.2044 0.028 Uiso 1 1 calc R . . H7B H 0.9035 0.6646 0.3301 0.028 Uiso 1 1 calc R . . H7C H 0.9768 0.7496 0.3510 0.028 Uiso 1 1 calc R . . N1S N 1.0000 1.0000 0.0000 0.0240(19) Uani 1 6 d S . 1 C1S C 1.0000 1.0000 0.0926(16) 0.021(3) Uani 0.50 3 d SP . 1 C2S C 1.0000 1.0000 0.2486(15) 0.031(3) Uani 0.50 3 d SP A 1 H2S1 H 0.9856 1.0376 0.2813 0.047 Uiso 0.17 1 calc PR A 1 H2S2 H 1.0520 1.0144 0.2813 0.047 Uiso 0.17 1 calc PR A 1 H2S3 H 0.9624 0.9480 0.2813 0.047 Uiso 0.17 1 calc PR A 1 Cl11 Cl 1.01929(12) 0.92751(12) 0.4223(2) 0.0337(5) Uani 0.50 1 d P . 2 C11 C 1.0000 1.0000 0.3654(14) 0.029(3) Uani 0.50 3 d SP . 2 H11 H 1.0000 1.0000 0.2650 0.043 Uiso 0.50 3 calc SPR . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0112(2) 0.0131(2) 0.0120(2) -0.00003(17) 0.00058(17) 0.00620(18) O1 0.0109(12) 0.0149(12) 0.0112(13) 0.0009(11) -0.0001(10) 0.0050(10) N1 0.0118(14) 0.0148(15) 0.0132(15) 0.0009(12) 0.0001(12) 0.0085(12) N2 0.0139(15) 0.0129(14) 0.0125(16) 0.0012(12) 0.0026(12) 0.0085(13) C3 0.0154(18) 0.0168(18) 0.0094(17) -0.0028(15) -0.0014(14) 0.0055(15) C4 0.0209(19) 0.023(2) 0.0112(18) 0.0038(15) 0.0030(15) 0.0117(17) C5 0.0173(18) 0.0142(18) 0.0128(18) -0.0003(14) -0.0043(15) 0.0076(15) C6 0.0199(19) 0.030(2) 0.0158(19) 0.0031(17) 0.0022(16) 0.0137(17) C7 0.0208(19) 0.0205(19) 0.017(2) 0.0010(16) -0.0031(16) 0.0125(16) N1S 0.025(3) 0.025(3) 0.022(5) 0.000 0.000 0.0125(16) C1S 0.015(4) 0.015(4) 0.034(9) 0.000 0.000 0.007(2) C2S 0.028(5) 0.028(5) 0.037(9) 0.000 0.000 0.014(2) Cl11 0.0410(12) 0.0308(11) 0.0352(13) -0.0033(9) 0.0044(10) 0.0223(10) C11 0.036(5) 0.036(5) 0.014(7) 0.000 0.000 0.018(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 O1 1.936(2) 11_565 ? Cu1 O1 1.938(2) . ? Cu1 N1 1.955(3) . ? Cu1 N2 1.958(3) 12_655 ? O1 Cu1 1.936(2) 12_655 ? O1 H1 0.841(10) . ? N1 C5 1.343(4) . ? N1 N2 1.377(4) . ? N2 C3 1.348(4) . ? N2 Cu1 1.958(3) 11_565 ? C3 C4 1.394(5) . ? C3 C6 1.493(5) . ? C4 C5 1.388(5) . ? C4 H4 0.9500 . ? C5 C7 1.495(5) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N1S C1S 0.923(16) . ? N1S C1S 0.923(16) 10_775 ? C1S C2S 1.55(2) . ? C1S C1S 1.85(3) 10_775 ? C2S H2S1 0.9800 . ? C2S H2S2 0.9800 . ? C2S H2S3 0.9800 . ? Cl11 C11 1.760(5) . ? Cl11 Cl11 2.274(3) 12_656 ? Cl11 Cl11 2.274(3) 11_566 ? C11 Cl11 1.760(5) 2_765 ? C11 Cl11 1.760(5) 3_675 ? C11 H11 1.0000 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 160.45(13) 11_565 . ? O1 Cu1 N1 85.26(10) 11_565 . ? O1 Cu1 N1 94.53(11) . . ? O1 Cu1 N2 96.89(10) 11_565 12_655 ? O1 Cu1 N2 86.38(10) . 12_655 ? N1 Cu1 N2 170.98(11) . 12_655 ? Cu1 O1 Cu1 110.25(11) 12_655 . ? Cu1 O1 H1 115(3) 12_655 . ? Cu1 O1 H1 112(3) . . ? C5 N1 N2 108.7(3) . . ? C5 N1 Cu1 134.4(2) . . ? N2 N1 Cu1 116.9(2) . . ? C3 N2 N1 108.1(3) . . ? C3 N2 Cu1 133.7(2) . 11_565 ? N1 N2 Cu1 117.5(2) . 11_565 ? N2 C3 C4 108.4(3) . . ? N2 C3 C6 122.4(3) . . ? C4 C3 C6 129.2(3) . . ? C5 C4 C3 106.2(3) . . ? C5 C4 H4 126.9 . . ? C3 C4 H4 126.9 . . ? N1 C5 C4 108.5(3) . . ? N1 C5 C7 122.2(3) . . ? C4 C5 C7 129.2(3) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1S N1S C1S 180.000(7) . 10_775 ? N1S C1S C2S 180.000(12) . . ? N1S C1S C1S 0.000(4) . 10_775 ? C2S C1S C1S 180.000(10) . 10_775 ? C11 Cl11 Cl11 82.7(3) . 12_656 ? C11 Cl11 Cl11 82.7(3) . 11_566 ? Cl11 Cl11 Cl11 78.73(14) 12_656 11_566 ? Cl11 C11 Cl11 110.1(4) 2_765 3_675 ? Cl11 C11 Cl11 110.1(4) 2_765 . ? Cl11 C11 Cl11 110.1(4) 3_675 . ? Cl11 C11 H11 108.8 2_765 . ? Cl11 C11 H11 108.8 3_675 . ? Cl11 C11 H11 108.8 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 Cu1 -56.70(19) 11_565 . . 12_655 ? N1 Cu1 O1 Cu1 -145.28(12) . . . 12_655 ? N2 Cu1 O1 Cu1 43.72(13) 12_655 . . 12_655 ? O1 Cu1 N1 C5 147.1(3) 11_565 . . . ? O1 Cu1 N1 C5 -52.5(3) . . . . ? N2 Cu1 N1 C5 42.9(9) 12_655 . . . ? O1 Cu1 N1 N2 -33.1(2) 11_565 . . . ? O1 Cu1 N1 N2 127.3(2) . . . . ? N2 Cu1 N1 N2 -137.2(6) 12_655 . . . ? C5 N1 N2 C3 0.1(3) . . . . ? Cu1 N1 N2 C3 -179.9(2) . . . . ? C5 N1 N2 Cu1 -171.8(2) . . . 11_565 ? Cu1 N1 N2 Cu1 8.3(3) . . . 11_565 ? N1 N2 C3 C4 -0.6(4) . . . . ? Cu1 N2 C3 C4 169.3(2) 11_565 . . . ? N1 N2 C3 C6 178.8(3) . . . . ? Cu1 N2 C3 C6 -11.2(5) 11_565 . . . ? N2 C3 C4 C5 0.9(4) . . . . ? C6 C3 C4 C5 -178.5(3) . . . . ? N2 N1 C5 C4 0.5(4) . . . . ? Cu1 N1 C5 C4 -179.6(2) . . . . ? N2 N1 C5 C7 -179.7(3) . . . . ? Cu1 N1 C5 C7 0.2(5) . . . . ? C3 C4 C5 N1 -0.9(4) . . . . ? C3 C4 C5 C7 179.4(3) . . . . ? C1S N1S C1S C2S 0(100) 10_775 . . . ? Cl11 Cl11 C11 Cl11 21.0(5) 12_656 . . 2_765 ? Cl11 Cl11 C11 Cl11 100.5(6) 11_566 . . 2_765 ? Cl11 Cl11 C11 Cl11 -100.5(6) 12_656 . . 3_675 ? Cl11 Cl11 C11 Cl11 -21.0(5) 11_566 . . 3_675 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.543 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 927863' ####################################################################### # # 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_sx307bb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H48 Cu6 N12 O6' _chemical_formula_weight 1054.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 20.1726(8) _cell_length_b 20.1726(8) _cell_length_c 10.1341(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3571.4(3) _cell_formula_units_Z 3 _cell_measurement_temperature 373(2) _cell_measurement_reflns_used 447 _cell_measurement_theta_min 3.4916 _cell_measurement_theta_max 28.8019 _exptl_crystal_description needle _exptl_crystal_colour violet _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.470 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1602 _exptl_absorpt_coefficient_mu 2.678 _exptl_absorpt_correction_T_min 0.56424 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 373(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0267 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3002 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.1306 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 28.87 _reflns_number_total 1796 _reflns_number_gt 897 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1451P)^2^+2.0280P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1796 _refine_ls_number_parameters 87 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1633 _refine_ls_R_factor_gt 0.0918 _refine_ls_wR_factor_ref 0.3015 _refine_ls_wR_factor_gt 0.2329 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.333 0.667 0.167 192 -1 ' ' 2 0.667 0.333 -0.167 192 -1 ' ' 3 0.000 0.000 0.500 193 0 ' ' _platon_squeeze_details ; ; 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 0.86696(7) 0.04089(7) -0.00252(11) 0.0453(6) Uani 1 1 d . . . O1 O 0.8207(5) -0.0518(4) 0.0997(8) 0.056(2) Uani 1 1 d D . . H1 H 0.787(6) -0.043(8) 0.135(11) 0.084 Uiso 1 1 d D . . N1 N 0.8146(5) -0.0223(5) -0.1565(7) 0.048(2) Uani 1 1 d . . . N2 N 0.7944(4) -0.0986(5) -0.1517(8) 0.046(2) Uani 1 1 d . . . C3 C 0.7560(7) -0.1302(6) -0.2634(10) 0.056(3) Uani 1 1 d . . . C4 C 0.7517(7) -0.0774(7) -0.3394(11) 0.065(3) Uani 1 1 d . . . H4 H 0.7279 -0.0852 -0.4210 0.079 Uiso 1 1 calc R . . C5 C 0.7894(7) -0.0110(6) -0.2717(10) 0.054(3) Uani 1 1 d . . . C6 C 0.7233(8) -0.2175(7) -0.2799(14) 0.078(4) Uani 1 1 d . . . H6A H 0.7206 -0.2400 -0.1952 0.116 Uiso 1 1 calc R . . H6B H 0.7561 -0.2262 -0.3370 0.116 Uiso 1 1 calc R . . H6C H 0.6730 -0.2402 -0.3177 0.116 Uiso 1 1 calc R . . C7 C 0.8063(9) 0.0702(8) -0.3093(12) 0.087(5) Uani 1 1 d . . . H7A H 0.7779 0.0851 -0.2523 0.131 Uiso 1 1 calc R . . H7B H 0.7913 0.0703 -0.3992 0.131 Uiso 1 1 calc R . . H7C H 0.8600 0.1057 -0.2996 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 0.0462(9) 0.0443(8) 0.0442(8) -0.0019(5) -0.0016(5) 0.0216(6) O1 0.079(6) 0.044(4) 0.050(4) 0.002(3) 0.003(4) 0.034(4) N1 0.051(5) 0.043(5) 0.049(5) -0.001(4) -0.010(4) 0.022(4) N2 0.042(5) 0.038(5) 0.051(5) -0.002(4) -0.008(4) 0.014(4) C3 0.059(7) 0.055(7) 0.050(6) -0.009(5) -0.010(5) 0.026(6) C4 0.090(9) 0.061(8) 0.046(6) -0.012(6) -0.022(6) 0.039(7) C5 0.060(7) 0.058(7) 0.051(6) 0.008(5) -0.007(5) 0.035(6) C6 0.085(10) 0.058(8) 0.081(9) -0.021(7) -0.018(8) 0.029(7) C7 0.121(13) 0.098(11) 0.073(9) 0.002(8) -0.020(9) 0.078(11) _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 1.922(7) . ? Cu1 N2 1.943(8) 11_665 ? Cu1 N1 1.956(8) . ? Cu1 O1 1.961(7) 11_665 ? O1 Cu1 1.961(7) 12_545 ? O1 H1 0.852(10) . ? N1 C5 1.338(12) . ? N1 N2 1.383(11) . ? N2 C3 1.339(12) . ? N2 Cu1 1.943(8) 12_545 ? C3 C4 1.350(15) . ? C3 C6 1.550(15) . ? C4 C5 1.351(14) . ? C4 H4 0.9300 . ? C5 C7 1.545(17) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 N2 93.9(3) . 11_665 ? O1 Cu1 N1 87.4(3) . . ? N2 Cu1 N1 168.4(3) 11_665 . ? O1 Cu1 O1 156.9(5) . 11_665 ? N2 Cu1 O1 86.5(3) 11_665 11_665 ? N1 Cu1 O1 96.8(3) . 11_665 ? Cu1 O1 Cu1 109.9(4) . 12_545 ? Cu1 O1 H1 95(9) . . ? Cu1 O1 H1 139(10) 12_545 . ? C5 N1 N2 107.1(8) . . ? C5 N1 Cu1 135.4(7) . . ? N2 N1 Cu1 117.4(6) . . ? C3 N2 N1 106.2(8) . . ? C3 N2 Cu1 136.4(7) . 12_545 ? N1 N2 Cu1 117.4(6) . 12_545 ? N2 C3 C4 110.9(10) . . ? N2 C3 C6 116.6(10) . . ? C4 C3 C6 132.5(10) . . ? C3 C4 C5 105.5(10) . . ? C3 C4 H4 127.3 . . ? C5 C4 H4 127.3 . . ? N1 C5 C4 110.3(10) . . ? N1 C5 C7 119.6(10) . . ? C4 C5 C7 130.1(10) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 Cu1 O1 Cu1 -149.0(4) 11_665 . . 12_545 ? N1 Cu1 O1 Cu1 42.5(4) . . . 12_545 ? O1 Cu1 O1 Cu1 -58.8(6) 11_665 . . 12_545 ? O1 Cu1 N1 C5 153.4(11) . . . . ? N2 Cu1 N1 C5 57(2) 11_665 . . . ? O1 Cu1 N1 C5 -49.3(11) 11_665 . . . ? O1 Cu1 N1 N2 -23.9(7) . . . . ? N2 Cu1 N1 N2 -120.6(15) 11_665 . . . ? O1 Cu1 N1 N2 133.4(7) 11_665 . . . ? C5 N1 N2 C3 -1.5(11) . . . . ? Cu1 N1 N2 C3 176.5(7) . . . . ? C5 N1 N2 Cu1 178.1(7) . . . 12_545 ? Cu1 N1 N2 Cu1 -3.9(9) . . . 12_545 ? N1 N2 C3 C4 0.7(13) . . . . ? Cu1 N2 C3 C4 -178.7(8) 12_545 . . . ? N1 N2 C3 C6 -177.3(10) . . . . ? Cu1 N2 C3 C6 3.3(17) 12_545 . . . ? N2 C3 C4 C5 0.4(14) . . . . ? C6 C3 C4 C5 177.9(13) . . . . ? N2 N1 C5 C4 1.8(13) . . . . ? Cu1 N1 C5 C4 -175.7(8) . . . . ? N2 N1 C5 C7 -177.5(10) . . . . ? Cu1 N1 C5 C7 5.1(17) . . . . ? C3 C4 C5 N1 -1.4(14) . . . . ? C3 C4 C5 C7 177.8(13) . . . . ? _diffrn_measured_fraction_theta_max 0.859 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.344 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.192 _database_code_depnum_ccdc_archive 'CCDC 927864' ####################################################################### # # 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_sx308bb _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H48 Cu6 N12 O6' _chemical_formula_weight 1054.04 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 19.8969(3) _cell_length_b 19.8969(3) _cell_length_c 9.9518(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3411.95(13) _cell_formula_units_Z 3 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7624 _cell_measurement_theta_min 3.1211 _cell_measurement_theta_max 30.4696 _exptl_crystal_description needle _exptl_crystal_colour violet _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.539 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1602 _exptl_absorpt_coefficient_mu 2.804 _exptl_absorpt_correction_T_min 0.80571 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0267 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23009 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.13 _diffrn_reflns_theta_max 30.54 _reflns_number_total 2329 _reflns_number_gt 2037 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1074P)^2^+80.8535P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2329 _refine_ls_number_parameters 91 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0748 _refine_ls_R_factor_gt 0.0662 _refine_ls_wR_factor_ref 0.2006 _refine_ls_wR_factor_gt 0.1915 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.333 0.667 0.167 162 8 ' ' 2 0.667 0.333 -0.167 162 8 ' ' 3 0.000 0.000 0.500 163 8 ' ' _platon_squeeze_details ; ; 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 0.17702(3) 0.04330(3) -0.00362(5) 0.0135(2) Uani 1 1 d . . . O1 O 0.1821(2) 0.1303(2) -0.0994(3) 0.0179(6) Uani 1 1 d D . . H1 H 0.172(4) 0.126(4) -0.1828(19) 0.027 Uiso 1 1 d D . . N1 N 0.2087(2) 0.1105(2) 0.1543(4) 0.0156(7) Uani 1 1 d . . . N2 N 0.1848(2) 0.1642(2) 0.1613(4) 0.0150(7) Uani 1 1 d . . . C3 C 0.2099(3) 0.2025(3) 0.2780(5) 0.0176(8) Uani 1 1 d . . . C4 C 0.2519(3) 0.1745(3) 0.3468(5) 0.0223(9) Uani 1 1 d . . . H4 H 0.2772 0.1917 0.4312 0.027 Uiso 1 1 calc R . . C5 C 0.2492(3) 0.1162(3) 0.2661(5) 0.0178(8) Uani 1 1 d . . . C6 C 0.1914(3) 0.2637(3) 0.3203(5) 0.0245(10) Uani 1 1 d . . . H6A H 0.1719 0.2793 0.2429 0.037 Uiso 1 1 calc R . . H6B H 0.2384 0.3089 0.3548 0.037 Uiso 1 1 calc R . . H6C H 0.1517 0.2430 0.3909 0.037 Uiso 1 1 calc R . . C7 C 0.2838(3) 0.0653(3) 0.2890(5) 0.0237(9) Uani 1 1 d . . . H7A H 0.2496 0.0219 0.3476 0.036 Uiso 1 1 calc R . . H7B H 0.3348 0.0956 0.3316 0.036 Uiso 1 1 calc R . . H7C H 0.2897 0.0450 0.2027 0.036 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 0.0148(3) 0.0121(3) 0.0137(3) -0.00098(16) 0.00015(17) 0.0068(2) O1 0.0263(17) 0.0178(15) 0.0152(15) -0.0010(11) -0.0011(12) 0.0153(13) N1 0.0180(17) 0.0148(16) 0.0165(17) -0.0028(13) -0.0039(13) 0.0100(14) N2 0.0166(16) 0.0152(16) 0.0160(16) -0.0021(13) -0.0027(13) 0.0101(14) C3 0.022(2) 0.0167(19) 0.0162(19) -0.0035(15) -0.0033(15) 0.0109(17) C4 0.031(2) 0.024(2) 0.016(2) -0.0032(17) -0.0072(17) 0.017(2) C5 0.020(2) 0.019(2) 0.0167(19) 0.0001(15) -0.0034(16) 0.0122(17) C6 0.037(3) 0.023(2) 0.020(2) -0.0052(17) -0.0031(19) 0.019(2) C7 0.029(2) 0.025(2) 0.025(2) 0.0018(18) -0.0056(18) 0.019(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 O1 1.933(3) 11 ? Cu1 O1 1.934(3) . ? Cu1 N1 1.953(4) . ? Cu1 N2 1.954(4) 11 ? O1 Cu1 1.933(3) 12 ? O1 H1 0.848(10) . ? N1 C5 1.345(6) . ? N1 N2 1.371(5) . ? N2 C3 1.341(6) . ? N2 Cu1 1.954(4) 12 ? C3 C4 1.395(6) . ? C3 C6 1.498(6) . ? C4 C5 1.390(7) . ? C4 H4 0.9500 . ? C5 C7 1.501(6) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 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 O1 Cu1 O1 157.2(2) 11 . ? O1 Cu1 N1 94.34(15) 11 . ? O1 Cu1 N1 85.96(15) . . ? O1 Cu1 N2 86.95(15) 11 11 ? O1 Cu1 N2 96.77(15) . 11 ? N1 Cu1 N2 169.81(16) . 11 ? Cu1 O1 Cu1 110.68(17) 12 . ? Cu1 O1 H1 115(5) 12 . ? Cu1 O1 H1 119(5) . . ? C5 N1 N2 108.6(4) . . ? C5 N1 Cu1 134.3(3) . . ? N2 N1 Cu1 117.1(3) . . ? C3 N2 N1 108.2(4) . . ? C3 N2 Cu1 133.7(3) . 12 ? N1 N2 Cu1 117.8(3) . 12 ? N2 C3 C4 109.0(4) . . ? N2 C3 C6 122.2(4) . . ? C4 C3 C6 128.8(4) . . ? C5 C4 C3 105.6(4) . . ? C5 C4 H4 127.2 . . ? C3 C4 H4 127.2 . . ? N1 C5 C4 108.7(4) . . ? N1 C5 C7 121.8(4) . . ? C4 C5 C7 129.5(4) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 Cu1 O1 Cu1 46.9(3) 11 . . 12 ? N1 Cu1 O1 Cu1 -44.65(19) . . . 12 ? N2 Cu1 O1 Cu1 145.21(18) 11 . . 12 ? O1 Cu1 N1 C5 52.5(5) 11 . . . ? O1 Cu1 N1 C5 -150.4(5) . . . . ? N2 Cu1 N1 C5 -44.4(12) 11 . . . ? O1 Cu1 N1 N2 -125.6(3) 11 . . . ? O1 Cu1 N1 N2 31.5(3) . . . . ? N2 Cu1 N1 N2 137.5(8) 11 . . . ? C5 N1 N2 C3 -0.6(5) . . . . ? Cu1 N1 N2 C3 177.9(3) . . . . ? C5 N1 N2 Cu1 173.7(3) . . . 12 ? Cu1 N1 N2 Cu1 -7.7(4) . . . 12 ? N1 N2 C3 C4 1.2(5) . . . . ? Cu1 N2 C3 C4 -171.9(4) 12 . . . ? N1 N2 C3 C6 -177.7(4) . . . . ? Cu1 N2 C3 C6 9.2(7) 12 . . . ? N2 C3 C4 C5 -1.3(6) . . . . ? C6 C3 C4 C5 177.6(5) . . . . ? N2 N1 C5 C4 -0.2(5) . . . . ? Cu1 N1 C5 C4 -178.4(4) . . . . ? N2 N1 C5 C7 -179.7(4) . . . . ? Cu1 N1 C5 C7 2.1(7) . . . . ? C3 C4 C5 N1 0.9(6) . . . . ? C3 C4 C5 C7 -179.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.54 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 4.680 _refine_diff_density_min -0.605 _refine_diff_density_rms 0.252 _database_code_depnum_ccdc_archive 'CCDC 927865'