# 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_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H13 Mn2 N6 O11' _chemical_formula_weight 695.30 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 0.277 0.056 -0.040 1374 353 ' ' 2 -0.010 0.556 -0.009 1368 348 ' ' _platon_squeeze_details ; ; 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' Mn Mn 0.3368 0.7283 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 18.871(13) _cell_length_b 18.123(13) _cell_length_c 14.501(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.280(9) _cell_angle_gamma 90.00 _cell_volume 4938(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3155 _cell_measurement_theta_min 2.165 _cell_measurement_theta_max 23.276 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.935 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1396 _exptl_absorpt_coefficient_mu 0.553 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.5456 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12363 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0905 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 25.00 _reflns_number_total 7476 _reflns_number_gt 4763 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0406P)^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 0.06(2) _refine_ls_number_reflns 7476 _refine_ls_number_parameters 416 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0502 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_restrained_S_all 0.904 _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 Mn1 Mn 0.15830(4) 0.28116(4) 0.39246(4) 0.0662(2) Uani 1 1 d . . . Mn2 Mn 0.29445(4) 0.21883(5) 0.57412(4) 0.0780(3) Uani 1 1 d . . . O1 O -0.03488(19) 0.2878(3) 0.6215(2) 0.1051(12) Uani 1 1 d . . . O2 O -0.0943(2) 0.3031(4) 0.7339(2) 0.131(2) Uani 1 1 d . . . O3 O 0.25216(15) 0.2874(3) 1.3219(2) 0.0924(11) Uani 1 1 d . . . O4 O 0.3203(2) 0.2722(4) 1.4522(3) 0.164(3) Uani 1 1 d . . . O5 O 0.5751(2) 0.1828(3) 1.4151(3) 0.1196(17) Uani 1 1 d . . . O6 O 0.6256(2) 0.2579(3) 1.3289(3) 0.126(2) Uani 1 1 d . . . O7 O 0.3421(2) 0.66786(19) 0.5977(2) 0.0814(10) Uani 1 1 d . . . O8 O 0.2530(3) 0.6346(3) 0.4957(4) 0.168(3) Uani 1 1 d . . . O9 O 0.17640(18) 0.3823(2) 0.4683(2) 0.0939(12) Uani 1 1 d . A . O10 O 0.2137(2) 0.2997(2) 0.5711(3) 0.0972(12) Uani 1 1 d . A . O11A O 0.249(3) 0.167(3) 0.700(3) 0.171(18) Uani 0.42(9) 1 d P A 1 O11B O 0.277(3) 0.132(4) 0.6796(19) 0.252(15) Uani 0.58(9) 1 d P A 2 N1 N 0.2916(2) 0.3832(3) 0.8769(3) 0.0870(14) Uani 1 1 d . . . N2 N 0.32064(19) 0.3374(3) 1.0316(2) 0.0911(15) Uani 1 1 d . . . N3 N 0.40987(19) 0.3947(2) 0.9485(2) 0.0704(11) Uani 1 1 d . . . N4 N 0.2096(2) 0.3257(4) 0.9631(3) 0.133(3) Uani 1 1 d . . . H4A H 0.2020 0.3088 1.0168 0.160 Uiso 1 1 calc R . . N5 N 0.43908(19) 0.3509(3) 1.0932(2) 0.0801(13) Uani 1 1 d . . . H5B H 0.4807 0.3669 1.0836 0.096 Uiso 1 1 calc R . . N6 N 0.3789(2) 0.4428(2) 0.8055(2) 0.0727(12) Uani 1 1 d . . . H6B H 0.4224 0.4573 0.8090 0.087 Uiso 1 1 calc R . . C1 C 0.2758(2) 0.3486(4) 0.9545(3) 0.097(2) Uani 1 1 d . . . C2 C 0.3866(2) 0.3628(3) 1.0222(3) 0.0777(15) Uani 1 1 d . . . C3 C 0.3571(2) 0.4056(3) 0.8793(3) 0.0671(13) Uani 1 1 d . . . C4 C 0.1494(3) 0.3252(5) 0.8954(3) 0.121(3) Uani 1 1 d . . . C5 C 0.1561(3) 0.3178(6) 0.7985(4) 0.152(4) Uani 1 1 d . . . H5A H 0.2006 0.3187 0.7759 0.182 Uiso 1 1 calc R . . C6 C 0.0940(3) 0.3091(5) 0.7378(4) 0.142(4) Uani 1 1 d . . . H6A H 0.0979 0.3016 0.6750 0.170 Uiso 1 1 calc R . . C7 C 0.0276(3) 0.3116(5) 0.7701(3) 0.117(3) Uani 1 1 d . . . C8 C 0.0243(3) 0.3062(7) 0.8641(4) 0.171(5) Uani 1 1 d . . . H8A H -0.0192 0.3001 0.8884 0.205 Uiso 1 1 calc R . . C9 C 0.0874(3) 0.3101(6) 0.9230(3) 0.163(5) Uani 1 1 d . . . H9A H 0.0848 0.3012 0.9857 0.195 Uiso 1 1 calc R . . C10 C -0.0381(4) 0.3031(5) 0.7079(3) 0.109(3) Uani 1 1 d . . . C11 C 0.4341(2) 0.3162(3) 1.1795(3) 0.0706(14) Uani 1 1 d . . . C12 C 0.3735(2) 0.3101(3) 1.2262(3) 0.0763(16) Uani 1 1 d . . . H12A H 0.3303 0.3275 1.1984 0.092 Uiso 1 1 calc R . . C13 C 0.3759(2) 0.2785(4) 1.3138(3) 0.0810(15) Uani 1 1 d . . . C14 C 0.4393(2) 0.2511(3) 1.3542(3) 0.0827(18) Uani 1 1 d . . . H14A H 0.4409 0.2286 1.4119 0.099 Uiso 1 1 calc R . . C15 C 0.5013(2) 0.2569(3) 1.3089(3) 0.0715(15) Uani 1 1 d . . . C16 C 0.4985(2) 0.2930(3) 1.2222(3) 0.0661(13) Uani 1 1 d . . . H16A H 0.5401 0.3011 1.1940 0.079 Uiso 1 1 calc R . . C17 C 0.3116(3) 0.2769(5) 1.3643(3) 0.105(2) Uani 1 1 d . . . C18 C 0.5727(3) 0.2314(4) 1.3540(3) 0.0743(15) Uani 1 1 d . . . C19 C 0.3349(2) 0.4594(3) 0.7227(3) 0.0645(13) Uani 1 1 d . . . C20 C 0.3374(2) 0.5311(3) 0.6871(3) 0.0674(13) Uani 1 1 d . . . H20A H 0.3651 0.5674 0.7181 0.081 Uiso 1 1 calc R . . C21 C 0.2969(3) 0.5464(3) 0.6034(4) 0.0784(15) Uani 1 1 d . . . C22 C 0.2536(3) 0.4916(3) 0.5588(3) 0.0701(14) Uani 1 1 d . . . H22A H 0.2251 0.5031 0.5049 0.084 Uiso 1 1 calc R . . C23 C 0.2531(2) 0.4236(3) 0.5926(3) 0.0650(12) Uani 1 1 d . A . C24 C 0.2937(2) 0.4058(3) 0.6774(3) 0.0733(14) Uani 1 1 d . . . H24A H 0.2923 0.3584 0.7018 0.088 Uiso 1 1 calc R . . C25 C 0.2987(3) 0.6235(3) 0.5616(4) 0.0852(17) Uani 1 1 d . . . C26 C 0.2107(3) 0.3656(4) 0.5409(3) 0.0758(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Mn1 0.0542(4) 0.0775(5) 0.0603(4) 0.0032(4) -0.0296(3) -0.0055(4) Mn2 0.0668(5) 0.0924(6) 0.0670(4) 0.0044(4) -0.0367(3) -0.0091(5) O1 0.083(2) 0.149(4) 0.077(2) 0.004(3) -0.0282(17) 0.002(3) O2 0.049(2) 0.270(7) 0.067(2) -0.015(3) -0.0270(18) -0.021(3) O3 0.0467(17) 0.154(3) 0.0732(18) 0.012(2) -0.0150(14) 0.002(2) O4 0.094(3) 0.320(8) 0.074(2) 0.071(4) -0.011(2) 0.022(4) O5 0.070(3) 0.175(5) 0.107(3) 0.048(3) -0.031(2) 0.013(3) O6 0.046(2) 0.230(7) 0.097(3) 0.046(3) -0.0216(19) 0.001(3) O7 0.085(3) 0.061(2) 0.094(2) 0.0036(19) -0.007(2) -0.008(2) O8 0.182(5) 0.078(3) 0.217(5) 0.058(3) -0.129(4) -0.027(3) O9 0.080(2) 0.105(3) 0.088(2) -0.013(2) -0.0398(19) -0.010(2) O10 0.083(3) 0.067(3) 0.137(3) -0.007(2) -0.012(2) -0.020(2) O11A 0.16(2) 0.23(3) 0.120(17) 0.076(15) 0.023(12) -0.06(2) O11B 0.21(2) 0.37(4) 0.191(16) -0.02(2) 0.090(18) -0.13(2) N1 0.043(2) 0.148(4) 0.065(2) 0.016(2) -0.0262(17) -0.001(3) N2 0.038(2) 0.170(5) 0.060(2) 0.034(2) -0.0210(16) -0.015(3) N3 0.048(2) 0.101(3) 0.057(2) 0.020(2) -0.0213(16) -0.001(2) N4 0.040(2) 0.285(8) 0.069(2) 0.057(3) -0.0212(19) -0.038(3) N5 0.037(2) 0.135(4) 0.062(2) 0.020(2) -0.0257(16) -0.006(2) N6 0.060(2) 0.085(3) 0.066(2) 0.017(2) -0.0323(18) -0.016(2) C1 0.040(3) 0.192(7) 0.054(3) 0.026(3) -0.019(2) -0.007(3) C2 0.042(3) 0.122(5) 0.064(3) 0.019(3) -0.027(2) 0.006(3) C3 0.045(3) 0.093(4) 0.061(3) 0.019(2) -0.012(2) 0.009(2) C4 0.039(3) 0.258(9) 0.063(3) 0.042(4) -0.017(2) -0.022(4) C5 0.054(3) 0.331(13) 0.069(3) 0.007(5) -0.010(3) -0.019(5) C6 0.065(4) 0.288(12) 0.069(3) 0.004(5) -0.015(3) -0.036(5) C7 0.045(3) 0.232(9) 0.068(3) 0.008(4) -0.022(2) -0.022(4) C8 0.051(3) 0.392(15) 0.067(3) -0.003(5) -0.009(2) -0.048(6) C9 0.041(3) 0.387(15) 0.058(3) 0.018(5) -0.011(2) -0.022(5) C10 0.068(4) 0.201(8) 0.054(3) 0.015(4) -0.022(3) -0.008(4) C11 0.052(3) 0.112(4) 0.045(2) 0.010(2) -0.013(2) -0.011(3) C12 0.048(3) 0.115(5) 0.061(3) 0.015(2) -0.020(2) 0.005(3) C13 0.050(3) 0.133(5) 0.056(2) 0.022(3) -0.011(2) -0.010(3) C14 0.048(3) 0.137(6) 0.058(2) 0.018(2) -0.020(2) 0.000(3) C15 0.048(3) 0.107(4) 0.055(2) 0.010(2) -0.020(2) 0.001(2) C16 0.036(2) 0.104(4) 0.054(2) 0.014(2) -0.0182(17) -0.009(3) C17 0.059(3) 0.182(6) 0.070(3) 0.022(4) -0.006(2) 0.025(4) C18 0.056(3) 0.112(5) 0.051(2) 0.001(3) -0.018(2) -0.003(3) C19 0.063(3) 0.067(3) 0.057(2) 0.006(2) -0.027(2) -0.002(2) C20 0.063(3) 0.058(3) 0.074(3) 0.002(2) -0.034(2) -0.006(2) C21 0.067(3) 0.069(4) 0.091(3) 0.026(3) -0.032(3) -0.011(3) C22 0.063(3) 0.082(4) 0.060(3) 0.002(2) -0.024(2) -0.001(3) C23 0.064(3) 0.064(3) 0.063(2) -0.008(2) -0.013(2) -0.002(3) C24 0.069(3) 0.069(3) 0.074(3) 0.001(2) -0.035(2) -0.004(3) C25 0.087(4) 0.066(4) 0.094(4) 0.023(3) -0.038(3) -0.011(3) C26 0.055(3) 0.099(5) 0.071(3) -0.006(3) -0.010(2) -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 Mn1 O7 2.058(4) 4_546 ? Mn1 O3 2.128(3) 1_554 ? Mn1 O2 2.137(3) 2_556 ? Mn1 O9 2.149(4) . ? Mn1 O1 2.322(4) 2_556 ? Mn1 C10 2.611(6) 2_556 ? Mn2 O8 1.998(4) 4_546 ? Mn2 O6 2.090(3) 2_657 ? Mn2 O4 2.111(5) 1_554 ? Mn2 O10 2.112(4) . ? Mn2 O11B 2.25(4) . ? Mn2 O11A 2.29(3) . ? Mn2 C18 2.636(5) 2_657 ? O1 C10 1.290(6) . ? O1 Mn1 2.322(4) 2_556 ? O2 C10 1.159(7) . ? O2 Mn1 2.137(3) 2_556 ? O3 C17 1.244(5) . ? O3 Mn1 2.128(3) 1_556 ? O4 C17 1.272(6) . ? O4 Mn2 2.111(5) 1_556 ? O5 C18 1.247(7) . ? O6 C18 1.195(6) . ? O6 Mn2 2.090(3) 2_657 ? O7 C25 1.231(6) . ? O7 Mn1 2.058(4) 4_556 ? O8 C25 1.243(6) . ? O8 Mn2 1.998(4) 4_556 ? O9 C26 1.222(5) . ? O10 C26 1.272(7) . ? N1 C3 1.298(6) . ? N1 C1 1.346(6) . ? N2 C2 1.346(6) . ? N2 C1 1.354(5) . ? N3 C2 1.324(6) . ? N3 C3 1.361(5) . ? N4 C1 1.333(6) . ? N4 C4 1.431(5) . ? N4 H4A 0.8600 . ? N5 C2 1.378(5) . ? N5 C11 1.411(6) . ? N5 H5B 0.8600 . ? N6 C3 1.359(6) . ? N6 C19 1.428(5) . ? N6 H6B 0.8600 . ? C4 C9 1.299(7) . ? C4 C5 1.430(7) . ? C5 C6 1.407(7) . ? C5 H5A 0.9300 . ? C6 C7 1.378(8) . ? C6 H6A 0.9300 . ? C7 C8 1.374(8) . ? C7 C10 1.472(7) . ? C8 C9 1.402(7) . ? C8 H8A 0.9300 . ? C9 H9A 0.9300 . ? C10 Mn1 2.611(6) 2_556 ? C11 C16 1.378(6) . ? C11 C12 1.386(7) . ? C12 C13 1.390(6) . ? C12 H12A 0.9300 . ? C13 C14 1.375(6) . ? C13 C17 1.474(7) . ? C14 C15 1.397(7) . ? C14 H14A 0.9300 . ? C15 C16 1.414(6) . ? C15 C18 1.514(6) . ? C16 H16A 0.9300 . ? C18 Mn2 2.636(5) 2_657 ? C19 C24 1.374(6) . ? C19 C20 1.400(6) . ? C20 C21 1.401(6) . ? C20 H20A 0.9300 . ? C21 C22 1.406(7) . ? C21 C25 1.524(7) . ? C22 C23 1.328(7) . ? C22 H22A 0.9300 . ? C23 C24 1.424(6) . ? C23 C26 1.482(7) . ? C24 H24A 0.9300 . ? 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 O7 Mn1 O3 95.48(18) 4_546 1_554 ? O7 Mn1 O2 103.8(2) 4_546 2_556 ? O3 Mn1 O2 90.42(15) 1_554 2_556 ? O7 Mn1 O9 144.81(14) 4_546 . ? O3 Mn1 O9 95.75(16) 1_554 . ? O2 Mn1 O9 109.3(2) 2_556 . ? O7 Mn1 O1 92.73(18) 4_546 2_556 ? O3 Mn1 O1 145.86(12) 1_554 2_556 ? O2 Mn1 O1 55.44(15) 2_556 2_556 ? O9 Mn1 O1 96.37(15) . 2_556 ? O7 Mn1 C10 100.4(2) 4_546 2_556 ? O3 Mn1 C10 116.30(17) 1_554 2_556 ? O2 Mn1 C10 25.89(15) 2_556 2_556 ? O9 Mn1 C10 104.1(2) . 2_556 ? O1 Mn1 C10 29.58(16) 2_556 2_556 ? O8 Mn2 O6 149.6(2) 4_546 2_657 ? O8 Mn2 O4 93.0(3) 4_546 1_554 ? O6 Mn2 O4 101.6(2) 2_657 1_554 ? O8 Mn2 O10 103.33(19) 4_546 . ? O6 Mn2 O10 104.69(19) 2_657 . ? O4 Mn2 O10 83.5(2) 1_554 . ? O8 Mn2 O11B 73.7(11) 4_546 . ? O6 Mn2 O11B 85.6(8) 2_657 . ? O4 Mn2 O11B 162.4(19) 1_554 . ? O10 Mn2 O11B 110(2) . . ? O8 Mn2 O11A 84.6(13) 4_546 . ? O6 Mn2 O11A 84.5(8) 2_657 . ? O4 Mn2 O11A 171.1(14) 1_554 . ? O10 Mn2 O11A 88.7(18) . . ? O11B Mn2 O11A 22.7(11) . . ? O8 Mn2 C18 129.3(2) 4_546 2_657 ? O6 Mn2 C18 26.17(16) 2_657 2_657 ? O4 Mn2 C18 90.41(17) 1_554 2_657 ? O10 Mn2 C18 127.34(18) . 2_657 ? O11B Mn2 C18 89.3(12) . 2_657 ? O11A Mn2 C18 97.7(9) . 2_657 ? C10 O1 Mn1 87.7(3) . 2_556 ? C10 O2 Mn1 100.5(3) . 2_556 ? C17 O3 Mn1 120.4(3) . 1_556 ? C17 O4 Mn2 148.4(6) . 1_556 ? C18 O6 Mn2 103.3(4) . 2_657 ? C25 O7 Mn1 132.4(4) . 4_556 ? C25 O8 Mn2 139.5(5) . 4_556 ? C26 O9 Mn1 106.0(4) . . ? C26 O10 Mn2 131.9(4) . . ? C3 N1 C1 114.1(3) . . ? C2 N2 C1 112.3(4) . . ? C2 N3 C3 112.6(4) . . ? C1 N4 C4 128.9(4) . . ? C1 N4 H4A 115.5 . . ? C4 N4 H4A 115.5 . . ? C2 N5 C11 129.1(4) . . ? C2 N5 H5B 115.5 . . ? C11 N5 H5B 115.5 . . ? C3 N6 C19 124.9(4) . . ? C3 N6 H6B 117.5 . . ? C19 N6 H6B 117.5 . . ? N4 C1 N1 120.4(4) . . ? N4 C1 N2 113.3(4) . . ? N1 C1 N2 126.1(4) . . ? N3 C2 N2 127.5(3) . . ? N3 C2 N5 113.7(4) . . ? N2 C2 N5 118.6(4) . . ? N1 C3 N6 119.3(3) . . ? N1 C3 N3 127.2(4) . . ? N6 C3 N3 113.5(4) . . ? C9 C4 C5 116.5(5) . . ? C9 C4 N4 118.1(4) . . ? C5 C4 N4 122.6(5) . . ? C6 C5 C4 118.8(5) . . ? C6 C5 H5A 120.6 . . ? C4 C5 H5A 120.6 . . ? C7 C6 C5 121.0(5) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C8 C7 C6 117.4(4) . . ? C8 C7 C10 119.2(5) . . ? C6 C7 C10 122.0(5) . . ? C7 C8 C9 119.1(5) . . ? C7 C8 H8A 120.4 . . ? C9 C8 H8A 120.4 . . ? C4 C9 C8 124.2(5) . . ? C4 C9 H9A 117.9 . . ? C8 C9 H9A 117.9 . . ? O2 C10 O1 116.3(5) . . ? O2 C10 C7 123.0(5) . . ? O1 C10 C7 120.4(6) . . ? O2 C10 Mn1 53.6(3) . 2_556 ? O1 C10 Mn1 62.7(3) . 2_556 ? C7 C10 Mn1 175.4(5) . 2_556 ? C16 C11 C12 119.3(4) . . ? C16 C11 N5 114.0(4) . . ? C12 C11 N5 126.5(4) . . ? C11 C12 C13 121.4(4) . . ? C11 C12 H12A 119.3 . . ? C13 C12 H12A 119.3 . . ? C14 C13 C12 119.4(4) . . ? C14 C13 C17 120.3(4) . . ? C12 C13 C17 120.2(4) . . ? C13 C14 C15 120.4(4) . . ? C13 C14 H14A 119.8 . . ? C15 C14 H14A 119.8 . . ? C14 C15 C16 119.2(4) . . ? C14 C15 C18 121.6(4) . . ? C16 C15 C18 118.9(4) . . ? C11 C16 C15 120.0(4) . . ? C11 C16 H16A 120.0 . . ? C15 C16 H16A 120.0 . . ? O3 C17 O4 122.1(5) . . ? O3 C17 C13 119.8(4) . . ? O4 C17 C13 117.7(4) . . ? O6 C18 O5 121.6(5) . . ? O6 C18 C15 118.7(5) . . ? O5 C18 C15 119.7(5) . . ? O6 C18 Mn2 50.5(3) . 2_657 ? O5 C18 Mn2 71.8(3) . 2_657 ? C15 C18 Mn2 166.8(5) . 2_657 ? C24 C19 C20 121.1(4) . . ? C24 C19 N6 120.8(4) . . ? C20 C19 N6 118.0(4) . . ? C19 C20 C21 118.0(4) . . ? C19 C20 H20A 121.0 . . ? C21 C20 H20A 121.0 . . ? C20 C21 C22 120.4(5) . . ? C20 C21 C25 119.8(4) . . ? C22 C21 C25 119.8(4) . . ? C23 C22 C21 120.6(4) . . ? C23 C22 H22A 119.7 . . ? C21 C22 H22A 119.7 . . ? C22 C23 C24 120.5(4) . . ? C22 C23 C26 119.6(4) . . ? C24 C23 C26 119.9(5) . . ? C19 C24 C23 119.2(4) . . ? C19 C24 H24A 120.4 . . ? C23 C24 H24A 120.4 . . ? O7 C25 O8 127.5(5) . . ? O7 C25 C21 117.8(4) . . ? O8 C25 C21 114.6(5) . . ? O9 C26 O10 122.2(5) . . ? O9 C26 C23 118.6(6) . . ? O10 C26 C23 119.1(4) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.521 _refine_diff_density_min -0.229 _refine_diff_density_rms 0.041 _database_code_depnum_ccdc_archive 'CCDC 931172' ####################################################################### # # 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_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H22 Cu4 N8 O17' _chemical_formula_weight 1032.73 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.008 -0.012 -0.001 3475 1045 ' ' _platon_squeeze_details ; ; loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 16.000(4) _cell_length_b 21.411(5) _cell_length_c 19.198(5) _cell_angle_alpha 90.00 _cell_angle_beta 99.861(3) _cell_angle_gamma 90.00 _cell_volume 6480(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4675 _cell_measurement_theta_min 2.154 _cell_measurement_theta_max 22.656 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.059 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2064 _exptl_absorpt_coefficient_mu 1.346 _exptl_absorpt_correction_type 'multi scan' _exptl_absorpt_correction_T_min 0.6546 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32284 _diffrn_reflns_av_R_equivalents 0.0506 _diffrn_reflns_av_sigmaI/netI 0.0655 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 25.00 _reflns_number_total 11391 _reflns_number_gt 7706 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Because the data was weak, the displacement parameters of several atoms (O13, C30, O14, O15 and N8) were restrained (DELU) to ensure stability of refinement ; _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^)+(0.0311P)^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 11391 _refine_ls_number_parameters 541 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0813 _refine_ls_wR_factor_gt 0.0775 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.36123(2) 0.649047(16) 1.02191(2) 0.02694(10) Uani 1 1 d . . . Cu2 Cu 0.48953(2) 0.772055(16) 1.09584(2) 0.02749(10) Uani 1 1 d . . . Cu3 Cu 0.31256(2) 0.738431(17) 1.12940(2) 0.02810(10) Uani 1 1 d . . . Cu4 Cu 0.18732(2) 0.625899(17) 1.08536(2) 0.02753(10) Uani 1 1 d . . . N2 N 0.77032(15) 0.78105(11) 0.95393(15) 0.0334(7) Uani 1 1 d . . . N1 N 0.83685(15) 0.85885(11) 0.89240(14) 0.0325(7) Uani 1 1 d . . . N3 N 0.89667(15) 0.75648(11) 0.90915(14) 0.0337(7) Uani 1 1 d . . . N5 N 0.82995(15) 0.68169(11) 0.96181(14) 0.0345(7) Uani 1 1 d . . . H5B H 0.8774 0.6624 0.9632 0.041 Uiso 1 1 calc R . . N6 N 0.95831(15) 0.83524(12) 0.85202(14) 0.0347(7) Uani 1 1 d . . . H6B H 0.9516 0.8713 0.8322 0.042 Uiso 1 1 calc R . . C19 C 1.03381(18) 0.80257(14) 0.84530(17) 0.0279(7) Uani 1 1 d . . . C16 C 0.77312(18) 0.58080(13) 0.97697(16) 0.0294(8) Uani 1 1 d . . . H16A H 0.8227 0.5641 0.9656 0.035 Uiso 1 1 calc R . . C2 C 0.83092(19) 0.74217(14) 0.94130(17) 0.0280(7) Uani 1 1 d . . . C3 C 0.89551(18) 0.81553(14) 0.88639(17) 0.0284(8) Uani 1 1 d . . . C12 C 0.69400(18) 0.66933(14) 1.00414(16) 0.0283(8) Uani 1 1 d . . . H12A H 0.6900 0.7121 1.0117 0.034 Uiso 1 1 calc R . . C15 C 0.70881(17) 0.54093(13) 0.98935(16) 0.0260(7) Uani 1 1 d . . . C11 C 0.76479(18) 0.64494(13) 0.98123(17) 0.0282(8) Uani 1 1 d . . . C1 C 0.77808(19) 0.83878(14) 0.92859(18) 0.0326(8) Uani 1 1 d . . . C14 C 0.63466(18) 0.56561(13) 1.00683(16) 0.0285(8) Uani 1 1 d . . . H14A H 0.5898 0.5395 1.0123 0.034 Uiso 1 1 calc R . . C24 C 1.06906(18) 0.81441(14) 0.78453(17) 0.0293(8) Uani 1 1 d . . . H24A H 1.0423 0.8414 0.7498 0.035 Uiso 1 1 calc R . . N4 N 0.71614(16) 0.87886(11) 0.94116(15) 0.0414(8) Uani 1 1 d . . . H4A H 0.6805 0.8629 0.9650 0.050 Uiso 1 1 calc R . . C4 C 0.7002(2) 0.94154(14) 0.92218(19) 0.0372(9) Uani 1 1 d . . . C20 C 1.07552(18) 0.76451(14) 0.89768(17) 0.0305(8) Uani 1 1 d . . . H20A H 1.0522 0.7571 0.9381 0.037 Uiso 1 1 calc R . . C5 C 0.7509(2) 0.97893(16) 0.8881(2) 0.0550(12) Uani 1 1 d . . . H5A H 0.7988 0.9623 0.8736 0.066 Uiso 1 1 calc R . . C18 C 0.71711(19) 0.47140(14) 0.98025(17) 0.0291(8) Uani 1 1 d . . . O5 O 0.65604(12) 0.43862(9) 0.99323(12) 0.0366(6) Uani 1 1 d . . . O6 O 0.78355(12) 0.45185(9) 0.96108(12) 0.0374(6) Uani 1 1 d . . . C6 C 0.7306(2) 1.04080(15) 0.8758(2) 0.0523(11) Uani 1 1 d . . . H6A H 0.7666 1.0659 0.8547 0.063 Uiso 1 1 calc R . . C7 C 0.65781(19) 1.06680(14) 0.89396(17) 0.0328(8) Uani 1 1 d . . . C8 C 0.6062(2) 1.02842(16) 0.9256(2) 0.0552(11) Uani 1 1 d . . . H8A H 0.5561 1.0443 0.9369 0.066 Uiso 1 1 calc R . . C10 C 0.6369(2) 1.13446(14) 0.88372(17) 0.0330(8) Uani 1 1 d . . . C9 C 0.6274(2) 0.96700(16) 0.9407(2) 0.0635(13) Uani 1 1 d . . . H9A H 0.5926 0.9424 0.9636 0.076 Uiso 1 1 calc R . . O1 O 0.69340(14) 1.17115(9) 0.87033(12) 0.0396(6) Uani 1 1 d . . . O2 O 0.56255(13) 1.14938(9) 0.88946(13) 0.0426(6) Uani 1 1 d . . . C23 C 1.14527(19) 0.78493(14) 0.77698(16) 0.0287(8) Uani 1 1 d . . . C21 C 1.15264(18) 0.73686(14) 0.89060(16) 0.0273(7) Uani 1 1 d . . . C25 C 1.2017(2) 0.70107(14) 0.95174(17) 0.0317(8) Uani 1 1 d . . . C22 C 1.18591(19) 0.74632(14) 0.82978(17) 0.0321(8) Uani 1 1 d . . . H22A H 1.2361 0.7265 0.8243 0.039 Uiso 1 1 calc R . . C26 C 1.1829(2) 0.79637(15) 0.71106(17) 0.0307(8) Uani 1 1 d . . . O8 O 1.26918(13) 0.67466(10) 0.94135(11) 0.0325(5) Uani 1 1 d . . . O7 O 1.17571(14) 0.70250(11) 1.00979(12) 0.0482(7) Uani 1 1 d . . . O9 O 1.24247(13) 0.76069(10) 0.70211(11) 0.0383(6) Uani 1 1 d . . . O10 O 1.15213(13) 0.83915(11) 0.67137(12) 0.0410(6) Uani 1 1 d . . . O11 O 0.30446(11) 0.64851(9) 1.11492(10) 0.0252(5) Uani 1 1 d . . . O12 O 0.38065(11) 0.73687(8) 1.05049(10) 0.0251(5) Uani 1 1 d . . . O13 O 0.45097(13) 0.72782(11) 1.19686(12) 0.0418(6) Uani 1 1 d U . . O4 O 0.48227(13) 0.62905(10) 1.02038(14) 0.0458(7) Uani 1 1 d . . . O3 O 0.56043(13) 0.70766(10) 1.06996(13) 0.0439(6) Uani 1 1 d . . . C13 C 0.62833(17) 0.62937(13) 1.01592(16) 0.0246(7) Uani 1 1 d . . . C17 C 0.54969(19) 0.65742(14) 1.03664(17) 0.0287(8) Uani 1 1 d . . . N7 N 0.5465(2) 0.72759(18) 1.29845(19) 0.0701(11) Uani 1 1 d . . . C30 C 0.4732(2) 0.73836(18) 1.2608(2) 0.0459(9) Uani 1 1 d U . . C31 C 0.6174(3) 0.7018(3) 1.2681(3) 0.113(2) Uani 1 1 d . . . H31A H 0.5981 0.6915 1.2193 0.170 Uiso 1 1 calc R . . H31B H 0.6383 0.6649 1.2936 0.170 Uiso 1 1 calc R . . H31C H 0.6619 0.7323 1.2715 0.170 Uiso 1 1 calc R . . C29 C 0.4170(3) 0.7652(3) 1.3087(3) 0.108(2) Uani 1 1 d . . . H29A H 0.3930 0.8048 1.2905 0.130 Uiso 1 1 calc R . . H29B H 0.3711 0.7367 1.3132 0.130 Uiso 1 1 calc R . . C28 C 0.4738(4) 0.7739(3) 1.3779(3) 0.124(2) Uani 1 1 d . . . H28A H 0.4498 0.7540 1.4154 0.149 Uiso 1 1 calc R . . H28B H 0.4812 0.8180 1.3888 0.149 Uiso 1 1 calc R . . C27 C 0.5581(3) 0.7442(3) 1.3712(3) 0.119(2) Uani 1 1 d . . . H27A H 0.6044 0.7735 1.3832 0.142 Uiso 1 1 calc R . . H27B H 0.5691 0.7076 1.4012 0.142 Uiso 1 1 calc R . . O14 O 0.59710(14) 0.81198(10) 1.14481(13) 0.0439(6) Uani 1 1 d U . . O17 O 0.06810(13) 0.60252(11) 1.05774(13) 0.0482(7) Uani 1 1 d . . . O15 O 0.59104(17) 0.84021(12) 1.03544(15) 0.0606(8) Uani 1 1 d U . . N8 N 0.6285(2) 0.84280(14) 1.0976(2) 0.0498(8) Uani 1 1 d U . . O16 O 0.69380(19) 0.87313(15) 1.11567(19) 0.0955(11) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0228(2) 0.0164(2) 0.0445(3) -0.00026(18) 0.01398(18) 0.00160(16) Cu2 0.0248(2) 0.0192(2) 0.0416(2) -0.00284(18) 0.01466(18) 0.00133(16) Cu3 0.0301(2) 0.0206(2) 0.0387(2) 0.00023(18) 0.02047(19) -0.00063(16) Cu4 0.0239(2) 0.0260(2) 0.0357(2) -0.00448(18) 0.01364(18) -0.00100(16) N2 0.0273(15) 0.0194(15) 0.0587(19) 0.0037(13) 0.0225(14) 0.0047(12) N1 0.0265(15) 0.0224(15) 0.0543(18) 0.0104(13) 0.0232(14) 0.0079(12) N3 0.0267(15) 0.0221(15) 0.0568(19) 0.0061(14) 0.0202(14) 0.0030(12) N5 0.0187(14) 0.0192(14) 0.071(2) 0.0071(14) 0.0242(14) 0.0039(11) N6 0.0316(16) 0.0324(16) 0.0471(18) 0.0177(14) 0.0266(14) 0.0113(12) C19 0.0224(17) 0.0277(18) 0.037(2) 0.0050(15) 0.0159(15) 0.0039(14) C16 0.0215(17) 0.0208(17) 0.049(2) 0.0027(15) 0.0139(16) 0.0042(13) C2 0.0253(18) 0.0220(18) 0.0384(19) 0.0024(15) 0.0103(15) 0.0002(14) C3 0.0187(17) 0.0254(18) 0.044(2) 0.0033(16) 0.0135(15) 0.0001(14) C12 0.0229(17) 0.0181(16) 0.047(2) -0.0005(15) 0.0131(16) -0.0004(13) C15 0.0198(17) 0.0197(16) 0.040(2) -0.0024(15) 0.0101(15) 0.0016(13) C11 0.0171(16) 0.0201(17) 0.049(2) 0.0020(15) 0.0100(15) 0.0000(13) C1 0.0266(19) 0.0235(18) 0.051(2) -0.0009(16) 0.0175(17) 0.0040(14) C14 0.0236(18) 0.0209(17) 0.044(2) -0.0009(15) 0.0143(15) -0.0060(13) C24 0.0239(18) 0.0269(18) 0.039(2) 0.0039(15) 0.0122(15) -0.0001(14) N4 0.0408(18) 0.0201(15) 0.073(2) 0.0083(15) 0.0370(16) 0.0054(13) C4 0.037(2) 0.0172(17) 0.063(2) 0.0054(17) 0.0242(18) 0.0066(15) C20 0.0246(18) 0.0355(19) 0.0355(19) 0.0077(16) 0.0164(15) 0.0006(15) C5 0.048(2) 0.026(2) 0.104(3) 0.013(2) 0.050(2) 0.0138(17) C18 0.0267(19) 0.0202(17) 0.042(2) -0.0009(15) 0.0119(16) 0.0032(14) O5 0.0287(13) 0.0171(12) 0.0700(17) -0.0067(11) 0.0254(12) -0.0023(10) O6 0.0251(12) 0.0211(12) 0.0705(17) -0.0105(11) 0.0209(12) 0.0003(9) C6 0.057(2) 0.023(2) 0.089(3) 0.010(2) 0.046(2) 0.0056(17) C7 0.0331(19) 0.0188(17) 0.050(2) 0.0008(16) 0.0165(17) 0.0049(14) C8 0.045(2) 0.027(2) 0.103(3) 0.008(2) 0.041(2) 0.0131(17) C10 0.038(2) 0.0235(18) 0.040(2) -0.0012(16) 0.0148(17) 0.0063(16) C9 0.056(3) 0.027(2) 0.124(4) 0.017(2) 0.062(3) 0.0107(18) O1 0.0436(14) 0.0195(12) 0.0644(17) 0.0031(11) 0.0341(13) 0.0025(10) O2 0.0332(14) 0.0196(12) 0.0793(18) -0.0037(12) 0.0216(13) 0.0050(10) C23 0.0255(18) 0.0314(19) 0.0318(19) 0.0056(15) 0.0120(15) 0.0008(14) C21 0.0253(18) 0.0279(18) 0.0318(18) 0.0066(15) 0.0139(15) 0.0037(14) C25 0.0309(19) 0.0299(19) 0.037(2) 0.0088(16) 0.0131(17) 0.0036(15) C22 0.0220(18) 0.035(2) 0.043(2) 0.0006(17) 0.0152(16) 0.0058(14) C26 0.034(2) 0.0299(19) 0.0300(19) 0.0038(16) 0.0095(16) -0.0014(16) O8 0.0289(13) 0.0363(13) 0.0321(13) 0.0038(11) 0.0049(10) 0.0073(10) O7 0.0434(15) 0.0644(18) 0.0425(15) 0.0250(13) 0.0233(13) 0.0238(12) O9 0.0406(14) 0.0378(14) 0.0448(14) 0.0101(11) 0.0308(12) 0.0146(11) O10 0.0332(14) 0.0515(16) 0.0438(15) 0.0205(13) 0.0219(12) 0.0151(11) O11 0.0217(11) 0.0223(11) 0.0345(12) -0.0001(10) 0.0128(10) -0.0029(9) O12 0.0222(11) 0.0178(11) 0.0386(13) 0.0003(10) 0.0142(10) 0.0028(9) O13 0.0368(14) 0.0516(16) 0.0385(12) 0.0009(12) 0.0111(11) -0.0028(11) O4 0.0211(13) 0.0261(13) 0.095(2) -0.0180(13) 0.0247(13) -0.0026(10) O3 0.0247(13) 0.0370(14) 0.0744(18) -0.0226(13) 0.0209(12) 0.0022(10) C13 0.0187(16) 0.0178(16) 0.0406(19) -0.0046(14) 0.0148(14) 0.0008(13) C17 0.0222(18) 0.0181(17) 0.050(2) 0.0018(16) 0.0177(16) 0.0027(14) N7 0.051(2) 0.103(3) 0.055(2) 0.005(2) 0.004(2) -0.002(2) C30 0.041(2) 0.054(3) 0.0412(14) 0.005(2) 0.0025(19) -0.0060(19) C31 0.069(4) 0.175(6) 0.101(4) 0.025(4) 0.030(3) 0.050(4) C29 0.068(3) 0.185(6) 0.069(4) -0.043(4) 0.004(3) 0.027(4) C28 0.098(5) 0.206(7) 0.066(4) -0.042(4) 0.010(3) 0.001(4) C27 0.084(4) 0.221(8) 0.048(3) -0.015(4) 0.001(3) 0.005(4) O14 0.0391(15) 0.0381(15) 0.0552(16) -0.0068(12) 0.0101(12) -0.0015(11) O17 0.0266(13) 0.0575(17) 0.0630(17) -0.0200(13) 0.0144(12) -0.0039(11) O15 0.0651(19) 0.0587(18) 0.0640(16) 0.0069(16) 0.0279(14) -0.0092(15) N8 0.042(2) 0.0353(18) 0.0758(17) -0.0044(17) 0.0202(15) -0.0029(15) O16 0.058(2) 0.086(2) 0.145(3) -0.014(2) 0.023(2) -0.0470(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 O5 1.912(2) 3_667 ? Cu1 O12 1.9685(19) . ? Cu1 O4 1.989(2) . ? Cu1 O8 2.020(2) 1_455 ? Cu1 O11 2.1376(19) . ? Cu1 Cu3 3.0130(7) . ? Cu2 O3 1.904(2) . ? Cu2 O2 1.919(2) 3_677 ? Cu2 O12 1.960(2) . ? Cu2 O14 2.006(2) . ? Cu2 O13 2.334(2) . ? Cu3 O9 1.9346(19) 4_476 ? Cu3 O1 1.938(2) 3_677 ? Cu3 O11 1.9464(19) . ? Cu3 O12 2.0120(18) . ? Cu3 O13 2.377(2) . ? Cu4 O11 1.9249(19) . ? Cu4 O17 1.955(2) . ? Cu4 O10 1.980(2) 4_476 ? Cu4 O6 1.981(2) 3_667 ? Cu4 O7 2.176(2) 1_455 ? N2 C2 1.331(4) . ? N2 C1 1.342(4) . ? N1 C1 1.332(4) . ? N1 C3 1.339(4) . ? N3 C3 1.337(4) . ? N3 C2 1.343(3) . ? N5 C2 1.354(4) . ? N5 C11 1.406(3) . ? N5 H5B 0.8600 . ? N6 C3 1.360(3) . ? N6 C19 1.421(3) . ? N6 H6B 0.8600 . ? C19 C20 1.375(4) . ? C19 C24 1.403(4) . ? C16 C11 1.383(4) . ? C16 C15 1.388(4) . ? C16 H16A 0.9300 . ? C12 C11 1.386(4) . ? C12 C13 1.403(4) . ? C12 H12A 0.9300 . ? C15 C14 1.391(4) . ? C15 C18 1.508(4) . ? C1 N4 1.363(4) . ? C14 C13 1.382(4) . ? C14 H14A 0.9300 . ? C24 C23 1.403(4) . ? C24 H24A 0.9300 . ? N4 C4 1.402(4) . ? N4 H4A 0.8600 . ? C4 C5 1.382(4) . ? C4 C9 1.386(4) . ? C20 C21 1.396(4) . ? C20 H20A 0.9300 . ? C5 C6 1.375(4) . ? C5 H5A 0.9300 . ? C18 O6 1.255(3) . ? C18 O5 1.262(3) . ? O5 Cu1 1.912(2) 3_667 ? O6 Cu4 1.981(2) 3_667 ? C6 C7 1.389(4) . ? C6 H6A 0.9300 . ? C7 C8 1.378(4) . ? C7 C10 1.492(4) . ? C8 C9 1.377(4) . ? C8 H8A 0.9300 . ? C10 O2 1.254(3) . ? C10 O1 1.258(4) . ? C9 H9A 0.9300 . ? O1 Cu3 1.938(2) 3_677 ? O2 Cu2 1.919(2) 3_677 ? C23 C22 1.381(4) . ? C23 C26 1.511(4) . ? C21 C22 1.379(4) . ? C21 C25 1.506(4) . ? C25 O7 1.255(3) . ? C25 O8 1.264(3) . ? C22 H22A 0.9300 . ? C26 O10 1.238(3) . ? C26 O9 1.257(3) . ? O8 Cu1 2.020(2) 1_655 ? O7 Cu4 2.176(2) 1_655 ? O9 Cu3 1.9346(19) 4_675 ? O10 Cu4 1.980(2) 4_675 ? O13 C30 1.239(4) . ? O4 C17 1.231(3) . ? O3 C17 1.248(3) . ? C13 C17 1.508(4) . ? N7 C30 1.288(4) . ? N7 C27 1.422(5) . ? N7 C31 1.468(5) . ? C30 C29 1.505(5) . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C29 C28 1.488(6) . ? C29 H29A 0.9700 . ? C29 H29B 0.9700 . ? C28 C27 1.518(7) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C27 H27A 0.9700 . ? C27 H27B 0.9700 . ? O14 N8 1.290(4) . ? O15 N8 1.243(4) . ? N8 O16 1.228(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O5 Cu1 O12 172.66(9) 3_667 . ? O5 Cu1 O4 84.38(8) 3_667 . ? O12 Cu1 O4 95.86(8) . . ? O5 Cu1 O8 94.74(9) 3_667 1_455 ? O12 Cu1 O8 90.79(8) . 1_455 ? O4 Cu1 O8 129.15(10) . 1_455 ? O5 Cu1 O11 92.90(8) 3_667 . ? O12 Cu1 O11 80.89(7) . . ? O4 Cu1 O11 124.43(9) . . ? O8 Cu1 O11 106.42(8) 1_455 . ? O5 Cu1 Cu3 132.85(6) 3_667 . ? O12 Cu1 Cu3 41.35(5) . . ? O4 Cu1 Cu3 120.89(7) . . ? O8 Cu1 Cu3 96.42(6) 1_455 . ? O11 Cu1 Cu3 40.06(5) . . ? O3 Cu2 O2 164.96(10) . 3_677 ? O3 Cu2 O12 97.45(9) . . ? O2 Cu2 O12 91.54(9) 3_677 . ? O3 Cu2 O14 85.94(9) . . ? O2 Cu2 O14 85.23(9) 3_677 . ? O12 Cu2 O14 176.58(8) . . ? O3 Cu2 O13 100.20(9) . . ? O2 Cu2 O13 92.87(9) 3_677 . ? O12 Cu2 O13 82.63(8) . . ? O14 Cu2 O13 96.38(9) . . ? O9 Cu3 O1 87.33(9) 4_476 3_677 ? O9 Cu3 O11 94.59(8) 4_476 . ? O1 Cu3 O11 170.47(9) 3_677 . ? O9 Cu3 O12 177.38(9) 4_476 . ? O1 Cu3 O12 92.97(8) 3_677 . ? O11 Cu3 O12 84.69(7) . . ? O9 Cu3 O13 102.06(9) 4_476 . ? O1 Cu3 O13 97.80(9) 3_677 . ? O11 Cu3 O13 90.93(8) . . ? O12 Cu3 O13 80.48(8) . . ? O9 Cu3 Cu1 138.60(7) 4_476 . ? O1 Cu3 Cu1 130.91(6) 3_677 . ? O11 Cu3 Cu1 44.97(5) . . ? O12 Cu3 Cu1 40.27(5) . . ? O13 Cu3 Cu1 89.23(6) . . ? O11 Cu4 O17 178.60(9) . . ? O11 Cu4 O10 93.48(8) . 4_476 ? O17 Cu4 O10 85.38(9) . 4_476 ? O11 Cu4 O6 92.96(8) . 3_667 ? O17 Cu4 O6 87.52(9) . 3_667 ? O10 Cu4 O6 144.59(10) 4_476 3_667 ? O11 Cu4 O7 88.55(9) . 1_455 ? O17 Cu4 O7 92.53(10) . 1_455 ? O10 Cu4 O7 105.49(9) 4_476 1_455 ? O6 Cu4 O7 109.45(9) 3_667 1_455 ? C2 N2 C1 113.2(2) . . ? C1 N1 C3 112.9(3) . . ? C3 N3 C2 113.4(2) . . ? C2 N5 C11 131.1(2) . . ? C2 N5 H5B 114.4 . . ? C11 N5 H5B 114.4 . . ? C3 N6 C19 127.0(3) . . ? C3 N6 H6B 116.5 . . ? C19 N6 H6B 116.5 . . ? C20 C19 C24 120.1(3) . . ? C20 C19 N6 122.6(3) . . ? C24 C19 N6 117.1(3) . . ? C11 C16 C15 121.2(3) . . ? C11 C16 H16A 119.4 . . ? C15 C16 H16A 119.4 . . ? N2 C2 N3 126.4(3) . . ? N2 C2 N5 120.0(3) . . ? N3 C2 N5 113.6(3) . . ? N3 C3 N1 126.7(3) . . ? N3 C3 N6 118.8(3) . . ? N1 C3 N6 114.5(3) . . ? C11 C12 C13 119.8(3) . . ? C11 C12 H12A 120.1 . . ? C13 C12 H12A 120.1 . . ? C16 C15 C14 119.7(3) . . ? C16 C15 C18 120.3(3) . . ? C14 C15 C18 119.9(3) . . ? C16 C11 C12 119.0(3) . . ? C16 C11 N5 117.2(2) . . ? C12 C11 N5 123.8(3) . . ? N1 C1 N2 127.1(3) . . ? N1 C1 N4 119.3(3) . . ? N2 C1 N4 113.6(3) . . ? C13 C14 C15 119.3(3) . . ? C13 C14 H14A 120.3 . . ? C15 C14 H14A 120.3 . . ? C23 C24 C19 119.0(3) . . ? C23 C24 H24A 120.5 . . ? C19 C24 H24A 120.5 . . ? C1 N4 C4 131.4(3) . . ? C1 N4 H4A 114.3 . . ? C4 N4 H4A 114.3 . . ? C5 C4 C9 118.7(3) . . ? C5 C4 N4 125.6(3) . . ? C9 C4 N4 115.7(3) . . ? C19 C20 C21 120.4(3) . . ? C19 C20 H20A 119.8 . . ? C21 C20 H20A 119.8 . . ? C6 C5 C4 120.0(3) . . ? C6 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? O6 C18 O5 126.6(3) . . ? O6 C18 C15 117.3(3) . . ? O5 C18 C15 116.1(2) . . ? C18 O5 Cu1 127.76(19) . 3_667 ? C18 O6 Cu4 133.5(2) . 3_667 ? C5 C6 C7 121.8(3) . . ? C5 C6 H6A 119.1 . . ? C7 C6 H6A 119.1 . . ? C8 C7 C6 117.6(3) . . ? C8 C7 C10 119.9(3) . . ? C6 C7 C10 122.4(3) . . ? C9 C8 C7 121.2(3) . . ? C9 C8 H8A 119.4 . . ? C7 C8 H8A 119.4 . . ? O2 C10 O1 125.8(3) . . ? O2 C10 C7 115.5(3) . . ? O1 C10 C7 118.7(3) . . ? C8 C9 C4 120.6(3) . . ? C8 C9 H9A 119.7 . . ? C4 C9 H9A 119.7 . . ? C10 O1 Cu3 125.9(2) . 3_677 ? C10 O2 Cu2 132.7(2) . 3_677 ? C22 C23 C24 120.1(3) . . ? C22 C23 C26 120.4(3) . . ? C24 C23 C26 119.4(3) . . ? C22 C21 C20 119.7(3) . . ? C22 C21 C25 120.6(3) . . ? C20 C21 C25 119.5(3) . . ? O7 C25 O8 125.0(3) . . ? O7 C25 C21 118.1(3) . . ? O8 C25 C21 116.8(3) . . ? C21 C22 C23 120.5(3) . . ? C21 C22 H22A 119.7 . . ? C23 C22 H22A 119.7 . . ? O10 C26 O9 126.6(3) . . ? O10 C26 C23 117.5(3) . . ? O9 C26 C23 115.9(3) . . ? C25 O8 Cu1 122.1(2) . 1_655 ? C25 O7 Cu4 124.8(2) . 1_655 ? C26 O9 Cu3 129.8(2) . 4_675 ? C26 O10 Cu4 130.8(2) . 4_675 ? Cu4 O11 Cu3 109.18(9) . . ? Cu4 O11 Cu1 106.66(9) . . ? Cu3 O11 Cu1 94.97(8) . . ? Cu2 O12 Cu1 125.23(9) . . ? Cu2 O12 Cu3 102.35(9) . . ? Cu1 O12 Cu3 98.38(8) . . ? C30 O13 Cu2 132.6(2) . . ? C30 O13 Cu3 127.2(2) . . ? Cu2 O13 Cu3 82.11(7) . . ? C17 O4 Cu1 134.7(2) . . ? C17 O3 Cu2 136.2(2) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 C17 120.6(2) . . ? C12 C13 C17 118.8(3) . . ? O4 C17 O3 126.4(3) . . ? O4 C17 C13 118.1(3) . . ? O3 C17 C13 115.5(3) . . ? C30 N7 C27 117.3(4) . . ? C30 N7 C31 122.4(4) . . ? C27 N7 C31 120.3(4) . . ? O13 C30 N7 127.1(4) . . ? O13 C30 C29 125.0(4) . . ? N7 C30 C29 107.9(4) . . ? N7 C31 H31A 109.5 . . ? N7 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? N7 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C28 C29 C30 104.9(4) . . ? C28 C29 H29A 110.8 . . ? C30 C29 H29A 110.8 . . ? C28 C29 H29B 110.8 . . ? C30 C29 H29B 110.8 . . ? H29A C29 H29B 108.9 . . ? C29 C28 C27 106.6(4) . . ? C29 C28 H28A 110.4 . . ? C27 C28 H28A 110.4 . . ? C29 C28 H28B 110.4 . . ? C27 C28 H28B 110.4 . . ? H28A C28 H28B 108.6 . . ? N7 C27 C28 102.7(4) . . ? N7 C27 H27A 111.2 . . ? C28 C27 H27A 111.2 . . ? N7 C27 H27B 111.2 . . ? C28 C27 H27B 111.2 . . ? H27A C27 H27B 109.1 . . ? N8 O14 Cu2 107.2(2) . . ? O16 N8 O15 122.8(4) . . ? O16 N8 O14 119.2(4) . . ? O15 N8 O14 118.0(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.583 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.070 _database_code_depnum_ccdc_archive 'CCDC 931173'