# 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_ilb1253_0m _database_code_depnum_ccdc_archive 'CCDC 912204' #TrackingRef '1_acetone.cif' _audit_creation_date 2013-01-07 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H28 Cu2 I4 O10' _chemical_formula_sum 'C34 H28 Cu2 I4 O10' _chemical_formula_weight 1231.24 _chemical_melting_point ? 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' 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.6678(5) _cell_length_b 11.9530(9) _cell_length_c 12.7015(10) _cell_angle_alpha 93.451(4) _cell_angle_beta 103.761(4) _cell_angle_gamma 102.981(4) _cell_volume 951.20(13) _cell_formula_units_Z 1 _cell_measurement_reflns_used 4979 _cell_measurement_temperature 100 _cell_measurement_theta_max 25.67 _cell_measurement_theta_min 3.25 _exptl_absorpt_coefficient_mu 4.417 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.731260 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0516 before and 0.0353 after correction. The Ratio of minimum to maximum transmission is 0.731260. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour 'clear light blue' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 2.149 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 582 _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_unetI/netI 0.0397 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 17854 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.99 _diffrn_reflns_theta_min 1.66 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _reflns_number_gt 3000 _reflns_number_total 3718 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.34A (Bruker, 200?)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.077 _refine_diff_density_min -0.654 _refine_diff_density_rms 0.126 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 3718 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0431 _refine_ls_R_factor_gt 0.0302 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0325P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.0661 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H6 of C6, H5 of C5, H16 of C16, H2 of C2, H13 of C13, H15 of C15, H12 of C12, H3 of C3 At 1.5 times of: {H21a,H21b,H21c} of C21, {H23a,H23b,H23c} of C23 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16) 2.b Idealised Me refined as rotating group: C21(H21a,H21b,H21c), C23(H23a,H23b,H23c) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.82971(7) 0.43130(4) 0.51649(4) 0.01712(12) Uani 1 1 d . . . O1 O 0.8114(4) 0.5704(2) 0.5986(2) 0.0212(6) Uani 1 1 d . . . C1 C 0.8999(6) 0.7665(3) 0.6735(3) 0.0185(9) Uani 1 1 d . . . C2 C 0.7122(6) 0.7525(4) 0.7062(3) 0.0215(9) Uani 1 1 d . . . H2 H 0.6076 0.6811 0.6855 0.026 Uiso 1 1 calc R . . O2 O 1.1000(4) 0.6913(2) 0.5689(2) 0.0232(6) Uani 1 1 d . . . C3 C 0.6754(6) 0.8418(4) 0.7689(3) 0.0243(10) Uani 1 1 d . . . H3 H 0.5457 0.8321 0.7900 0.029 Uiso 1 1 calc R . . I4 I 0.78271(5) 1.07699(3) 0.90191(3) 0.03659(11) Uani 1 1 d . . . C4 C 0.8310(7) 0.9450(4) 0.7999(3) 0.0240(10) Uani 1 1 d . . . C5 C 1.0199(7) 0.9613(4) 0.7686(3) 0.0260(10) Uani 1 1 d . . . H5 H 1.1257 1.0322 0.7910 0.031 Uiso 1 1 calc R . . C6 C 1.0520(7) 0.8730(4) 0.7042(3) 0.0242(10) Uani 1 1 d . . . H6 H 1.1790 0.8845 0.6804 0.029 Uiso 1 1 calc R . . C7 C 0.9390(6) 0.6686(3) 0.6084(3) 0.0191(9) Uani 1 1 d . . . O11 O 1.0211(4) 0.3996(2) 0.6481(2) 0.0230(6) Uani 1 1 d . . . C11 C 1.3552(6) 0.4171(3) 0.7747(3) 0.0185(9) Uani 1 1 d . . . O12 O 1.3116(4) 0.5201(2) 0.6201(2) 0.0210(6) Uani 1 1 d . . . C12 C 1.5766(6) 0.4494(3) 0.7957(3) 0.0208(9) Uani 1 1 d . . . H12 H 1.6423 0.4908 0.7462 0.025 Uiso 1 1 calc R . . C13 C 1.6995(6) 0.4208(4) 0.8889(3) 0.0223(9) Uani 1 1 d . . . H13 H 1.8505 0.4418 0.9034 0.027 Uiso 1 1 calc R . . I14 I 1.79548(4) 0.31912(2) 1.10288(2) 0.02427(9) Uani 1 1 d . . . C14 C 1.6032(6) 0.3615(3) 0.9616(3) 0.0210(9) Uani 1 1 d . . . C15 C 1.3826(6) 0.3291(4) 0.9422(3) 0.0237(10) Uani 1 1 d . . . H15 H 1.3178 0.2892 0.9927 0.028 Uiso 1 1 calc R . . C16 C 1.2588(6) 0.3564(4) 0.8473(3) 0.0236(10) Uani 1 1 d . . . H16 H 1.1079 0.3336 0.8320 0.028 Uiso 1 1 calc R . . C17 C 1.2190(6) 0.4490(3) 0.6729(3) 0.0196(9) Uani 1 1 d . . . O21 O 0.5495(4) 0.3134(2) 0.5492(2) 0.0231(6) Uani 1 1 d . . . C21 C 0.6867(7) 0.1483(4) 0.5870(4) 0.0390(12) Uani 1 1 d . . . H21A H 0.7192 0.1367 0.5164 0.059 Uiso 1 1 calc R . . H21B H 0.6337 0.0730 0.6102 0.059 Uiso 1 1 calc R . . H21C H 0.8162 0.1910 0.6415 0.059 Uiso 1 1 calc R . . C22 C 0.5200(7) 0.2158(4) 0.5761(3) 0.0247(10) Uani 1 1 d . . . C23 C 0.3141(7) 0.1600(4) 0.6006(4) 0.0380(12) Uani 1 1 d . . . H23A H 0.2151 0.2098 0.5841 0.057 Uiso 1 1 calc R . . H23B H 0.3405 0.1487 0.6781 0.057 Uiso 1 1 calc R . . H23C H 0.2521 0.0849 0.5558 0.057 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 0.0198(3) 0.0175(3) 0.0140(3) 0.0026(2) 0.0045(2) 0.0040(2) O1 0.0241(15) 0.0180(16) 0.0208(15) 0.0018(12) 0.0062(12) 0.0032(13) C1 0.027(2) 0.020(2) 0.010(2) 0.0053(16) 0.0012(17) 0.0120(18) C2 0.024(2) 0.019(2) 0.021(2) 0.0010(17) 0.0050(18) 0.0032(18) O2 0.0262(15) 0.0195(16) 0.0278(17) 0.0013(13) 0.0141(13) 0.0061(13) C3 0.025(2) 0.027(2) 0.025(2) 0.0067(19) 0.0115(19) 0.0084(19) I4 0.0503(2) 0.02782(18) 0.0376(2) -0.00396(14) 0.02220(15) 0.01221(15) C4 0.034(2) 0.022(2) 0.021(2) 0.0029(18) 0.0151(19) 0.010(2) C5 0.032(2) 0.015(2) 0.030(2) -0.0022(18) 0.012(2) 0.0008(19) C6 0.030(2) 0.021(2) 0.023(2) 0.0054(18) 0.0105(19) 0.0059(19) C7 0.025(2) 0.021(2) 0.014(2) 0.0073(17) 0.0027(18) 0.0111(19) O11 0.0205(15) 0.0260(17) 0.0201(15) 0.0056(12) 0.0014(12) 0.0038(13) C11 0.023(2) 0.017(2) 0.014(2) -0.0028(17) 0.0026(17) 0.0041(17) O12 0.0221(15) 0.0245(16) 0.0163(15) 0.0068(12) 0.0045(12) 0.0047(13) C12 0.025(2) 0.021(2) 0.017(2) -0.0002(17) 0.0076(18) 0.0048(18) C13 0.020(2) 0.026(2) 0.021(2) 0.0003(18) 0.0058(18) 0.0060(18) I14 0.02937(16) 0.02721(17) 0.01691(15) 0.00459(11) 0.00300(12) 0.01099(12) C14 0.030(2) 0.024(2) 0.011(2) 0.0003(17) 0.0048(17) 0.0110(19) C15 0.026(2) 0.029(3) 0.022(2) 0.0111(19) 0.0129(18) 0.0096(19) C16 0.021(2) 0.028(2) 0.022(2) 0.0036(19) 0.0044(18) 0.0066(19) C17 0.027(2) 0.014(2) 0.020(2) -0.0029(17) 0.0067(18) 0.0097(18) O21 0.0266(15) 0.0240(17) 0.0197(15) 0.0054(13) 0.0091(12) 0.0041(13) C21 0.042(3) 0.025(3) 0.056(3) 0.012(2) 0.022(3) 0.010(2) C22 0.028(2) 0.027(3) 0.019(2) 0.0040(19) 0.0066(19) 0.006(2) C23 0.031(3) 0.037(3) 0.049(3) 0.010(2) 0.018(2) 0.003(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 Cu1 2.6248(10) 2_766 ? Cu1 O1 1.952(3) . ? Cu1 O2 1.975(3) 2_766 ? Cu1 O11 1.961(3) . ? Cu1 O12 1.955(3) 2_766 ? Cu1 O21 2.215(3) . ? O1 C7 1.264(5) . ? C1 C2 1.388(6) . ? C1 C6 1.404(6) . ? C1 C7 1.498(5) . ? C2 H2 0.9500 . ? C2 C3 1.394(6) . ? O2 Cu1 1.975(3) 2_766 ? O2 C7 1.273(5) . ? C3 H3 0.9500 . ? C3 C4 1.388(6) . ? I4 C4 2.110(4) . ? C4 C5 1.386(6) . ? C5 H5 0.9500 . ? C5 C6 1.382(6) . ? C6 H6 0.9500 . ? O11 C17 1.273(5) . ? C11 C12 1.395(5) . ? C11 C16 1.394(6) . ? C11 C17 1.516(5) . ? O12 Cu1 1.955(3) 2_766 ? O12 C17 1.258(5) . ? C12 H12 0.9500 . ? C12 C13 1.379(5) . ? C13 H13 0.9500 . ? C13 C14 1.387(6) . ? I14 C14 2.104(4) . ? C14 C15 1.391(6) . ? C15 H15 0.9500 . ? C15 C16 1.391(5) . ? C16 H16 0.9500 . ? O21 C22 1.222(5) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C21 C22 1.500(6) . ? C22 C23 1.498(6) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 Cu1 83.52(8) . 2_766 ? O1 Cu1 O2 169.15(12) . 2_766 ? O1 Cu1 O11 89.11(11) . . ? O1 Cu1 O12 90.58(11) . 2_766 ? O1 Cu1 O21 96.65(11) . . ? O2 Cu1 Cu1 85.69(8) 2_766 2_766 ? O2 Cu1 O21 94.09(11) 2_766 . ? O11 Cu1 Cu1 86.13(8) . 2_766 ? O11 Cu1 O2 89.03(11) . 2_766 ? O11 Cu1 O21 91.87(11) . . ? O12 Cu1 Cu1 83.05(8) 2_766 2_766 ? O12 Cu1 O2 89.24(11) 2_766 2_766 ? O12 Cu1 O11 169.14(11) 2_766 . ? O12 Cu1 O21 98.94(11) 2_766 . ? O21 Cu1 Cu1 178.00(8) . 2_766 ? C7 O1 Cu1 124.5(3) . . ? C2 C1 C6 118.7(4) . . ? C2 C1 C7 120.1(4) . . ? C6 C1 C7 121.2(4) . . ? C1 C2 H2 119.6 . . ? C1 C2 C3 120.8(4) . . ? C3 C2 H2 119.6 . . ? C7 O2 Cu1 120.7(3) . 2_766 ? C2 C3 H3 120.5 . . ? C4 C3 C2 119.0(4) . . ? C4 C3 H3 120.5 . . ? C3 C4 I4 119.0(3) . . ? C5 C4 C3 121.4(4) . . ? C5 C4 I4 119.5(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 C4 119.0(4) . . ? C6 C5 H5 120.5 . . ? C1 C6 H6 119.5 . . ? C5 C6 C1 121.1(4) . . ? C5 C6 H6 119.5 . . ? O1 C7 C1 117.5(4) . . ? O1 C7 O2 125.6(4) . . ? O2 C7 C1 116.9(4) . . ? C17 O11 Cu1 120.2(3) . . ? C12 C11 C16 120.2(4) . . ? C12 C11 C17 119.8(4) . . ? C16 C11 C17 120.0(4) . . ? C17 O12 Cu1 124.4(2) . 2_766 ? C11 C12 H12 120.3 . . ? C13 C12 C11 119.5(4) . . ? C13 C12 H12 120.3 . . ? C12 C13 H13 119.9 . . ? C12 C13 C14 120.1(4) . . ? C14 C13 H13 119.9 . . ? C13 C14 I14 119.1(3) . . ? C13 C14 C15 121.2(4) . . ? C15 C14 I14 119.7(3) . . ? C14 C15 H15 120.7 . . ? C16 C15 C14 118.6(4) . . ? C16 C15 H15 120.7 . . ? C11 C16 H16 119.8 . . ? C15 C16 C11 120.3(4) . . ? C15 C16 H16 119.8 . . ? O11 C17 C11 116.5(3) . . ? O12 C17 O11 126.1(4) . . ? O12 C17 C11 117.4(3) . . ? C22 O21 Cu1 132.6(3) . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C22 C21 H21A 109.5 . . ? C22 C21 H21B 109.5 . . ? C22 C21 H21C 109.5 . . ? O21 C22 C21 121.9(4) . . ? O21 C22 C23 120.4(4) . . ? C23 C22 C21 117.7(4) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 Cu1 Cu1 O1 C7 1.8(3) 2_766 . . . ? Cu1 Cu1 O11 C17 0.7(3) 2_766 . . . ? Cu1 Cu1 O21 C22 -40(3) 2_766 . . . ? Cu1 O1 C7 C1 179.3(2) . . . . ? Cu1 O1 C7 O2 -1.6(5) . . . . ? Cu1 O2 C7 O1 0.0(5) 2_766 . . . ? Cu1 O2 C7 C1 179.1(2) 2_766 . . . ? Cu1 O11 C17 C11 -178.7(2) . . . . ? Cu1 O11 C17 O12 0.3(5) . . . . ? Cu1 O12 C17 O11 -1.6(6) 2_766 . . . ? Cu1 O12 C17 C11 177.4(2) 2_766 . . . ? Cu1 O21 C22 C21 -3.9(6) . . . . ? Cu1 O21 C22 C23 175.5(3) . . . . ? O1 Cu1 O11 C17 -82.9(3) . . . . ? O1 Cu1 O21 C22 -135.0(4) . . . . ? C1 C2 C3 C4 -1.0(6) . . . . ? C2 C1 C6 C5 2.0(6) . . . . ? C2 C1 C7 O1 -9.8(5) . . . . ? C2 C1 C7 O2 171.0(3) . . . . ? C2 C3 C4 I4 -176.7(3) . . . . ? C2 C3 C4 C5 0.9(6) . . . . ? O2 Cu1 O1 C7 7.8(8) 2_766 . . . ? O2 Cu1 O11 C17 86.4(3) 2_766 . . . ? O2 Cu1 O21 C22 43.5(4) 2_766 . . . ? C3 C4 C5 C6 0.6(6) . . . . ? I4 C4 C5 C6 178.2(3) . . . . ? C4 C5 C6 C1 -2.1(6) . . . . ? C6 C1 C2 C3 -0.4(6) . . . . ? C6 C1 C7 O1 169.1(4) . . . . ? C6 C1 C7 O2 -10.0(5) . . . . ? C7 C1 C2 C3 178.5(3) . . . . ? C7 C1 C6 C5 -176.9(3) . . . . ? O11 Cu1 O1 C7 88.0(3) . . . . ? O11 Cu1 O21 C22 -45.7(4) . . . . ? C11 C12 C13 C14 -0.7(6) . . . . ? O12 Cu1 O1 C7 -81.2(3) 2_766 . . . ? O12 Cu1 O11 C17 5.6(8) 2_766 . . . ? O12 Cu1 O21 C22 133.3(4) 2_766 . . . ? C12 C11 C16 C15 1.0(6) . . . . ? C12 C11 C17 O11 167.6(4) . . . . ? C12 C11 C17 O12 -11.5(5) . . . . ? C12 C13 C14 I14 179.9(3) . . . . ? C12 C13 C14 C15 0.3(6) . . . . ? C13 C14 C15 C16 0.6(6) . . . . ? I14 C14 C15 C16 -179.0(3) . . . . ? C14 C15 C16 C11 -1.3(6) . . . . ? C16 C11 C12 C13 0.0(6) . . . . ? C16 C11 C17 O11 -12.9(5) . . . . ? C16 C11 C17 O12 168.1(4) . . . . ? C17 C11 C12 C13 179.5(4) . . . . ? C17 C11 C16 C15 -178.5(4) . . . . ? O21 Cu1 O1 C7 179.7(3) . . . . ? O21 Cu1 O11 C17 -179.5(3) . . . . ? data_twin4 _database_code_depnum_ccdc_archive 'CCDC 912205' #TrackingRef '2_DMSO_twin.cif' _audit_creation_date 2013-01-07 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C32 H28 Cu2 I4 O10 S2' _chemical_formula_sum 'C32 H28 Cu2 I4 O10 S2' _chemical_formula_weight 1271.34 _chemical_melting_point ? 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 6.5847(5) _cell_length_b 15.8533(13) _cell_length_c 18.2578(15) _cell_angle_alpha 92.436(6) _cell_angle_beta 90.283(6) _cell_angle_gamma 93.469(6) _cell_volume 1900.7(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2665 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 25.282 _cell_measurement_theta_min 2.58 _exptl_absorpt_coefficient_mu 4.530 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.70 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2008/4 (Bruker,2010) was used for absorption correction. For component 1: wR2(int) was 0.0765 before and 0.0554 after correction. The Ratio of minimum to maximum transmission is 0.70. The \l/2 correction factor is Not present For component 2: wR2(int) was 0.1212 before and 0.0831 after correction. The Ratio of minimum to maximum transmission is 0.70. The \l/2 correction factor is Not present ; _exptl_crystal_colour 'clear dark blue' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 2.221 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1204 _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0738 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 8615 _diffrn_reflns_theta_full 27.59 _diffrn_reflns_theta_max 27.59 _diffrn_reflns_theta_min 1.12 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.977 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 5951 _reflns_number_total 8615 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.516 _refine_diff_density_min -1.261 _refine_diff_density_rms 0.224 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 455 _refine_ls_number_reflns 8615 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0512 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1190 _refine_ls_wR_factor_ref 0.1300 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H17 of C17, H20 of C20, H11 of C11, H28 of C28, H13 of C13, H4 of C4, H24 of C24, H10 of C10, H3 of C3, H27 of C27, H25 of C25, H21 of C21, H6 of C6, H14 of C14, H7 of C7, H18 of C18 At 1.5 times of: {H30a,H30b,H30c} of C30, {H32a,H32b,H32c} of C32, {H29a,H29b,H29c} of C29, {H31a,H31b,H31c} of C31 2. Uiso/Uaniso restraints and constraints Uanis(C1) ~ Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 Uanis(C15) ~ Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01 3.a Aromatic/amide H refined with riding coordinates: C24(H24), C17(H17), C6(H6), C14(H14), C10(H10), C13(H13), C3(H3), C4(H4), C21(H21), C28(H28), C7(H7), C18(H18), C20(H20), C25(H25), C27(H27), C11(H11) 3.b Idealised Me refined as rotating group: C30(H30a,H30b,H30c), C29(H29a,H29b,H29c), C31(H31a,H31b,H31c), C32(H32a,H32b, H32c) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I1 I -0.43219(9) -0.25882(3) 0.67763(3) 0.02676(15) Uani 1 1 d . . . I2 I 0.97542(9) 0.72232(4) 0.84737(3) 0.02909(15) Uani 1 1 d . . . I3 I 0.82987(8) 0.04820(3) 1.13800(3) 0.02062(13) Uani 1 1 d . . . I4 I -0.32471(8) 0.46844(3) 0.36261(3) 0.02097(13) Uani 1 1 d . . . Cu5 Cu 0.39613(14) 0.21468(6) 0.70177(5) 0.0149(2) Uani 1 1 d . . . Cu6 Cu 0.09801(14) 0.26740(6) 0.78437(5) 0.0150(2) Uani 1 1 d . . . S7 S -0.0925(3) 0.31493(13) 0.94123(11) 0.0217(4) Uani 1 1 d . . . S8 S 0.5985(3) 0.09955(13) 0.57253(11) 0.0250(5) Uani 1 1 d . . . O5 O 0.5280(8) 0.3244(3) 0.7324(3) 0.0198(12) Uani 1 1 d . . . C8 C 0.0876(12) 0.2998(5) 0.6315(4) 0.0180(16) Uani 1 1 d . . . O10 O -0.0149(9) 0.1516(3) 0.7630(3) 0.0204(12) Uani 1 1 d . . . O4 O -0.0059(8) 0.3047(3) 0.6918(3) 0.0192(12) Uani 1 1 d . . . O7 O 0.4788(8) 0.1660(3) 0.7939(3) 0.0188(12) Uani 1 1 d . . . O8 O 0.2530(8) 0.2268(3) 0.8672(3) 0.0189(12) Uani 1 1 d . . . O6 O 0.2653(9) 0.3744(3) 0.7961(3) 0.0234(13) Uani 1 1 d . . . O9 O 0.2167(9) 0.1109(3) 0.6798(3) 0.0224(12) Uani 1 1 d . . . C24 C 0.6937(12) 0.1191(5) 0.9173(4) 0.0181(16) Uani 1 1 d . . . H24 H 0.7621 0.1181 0.8716 0.022 Uiso 1 1 calc R . . O1 O -0.1312(8) 0.3092(3) 0.8596(3) 0.0192(12) Uani 1 1 d . . . C12 C -0.1887(12) 0.4101(5) 0.4512(4) 0.0164(16) Uani 1 1 d . . . C16 C 0.5711(12) 0.4607(5) 0.7905(4) 0.0166(16) Uani 1 1 d . . . O3 O 0.2574(8) 0.2688(3) 0.6213(3) 0.0218(12) Uani 1 1 d . . . O2 O 0.6344(9) 0.1681(3) 0.6319(3) 0.0208(12) Uani 1 1 d . . . C9 C -0.0121(12) 0.3372(5) 0.5667(4) 0.0168(16) Uani 1 1 d . . . C26 C 0.6845(13) 0.0906(5) 1.0448(4) 0.0186(16) Uani 1 1 d . . . C5 C -0.2731(13) -0.1407(5) 0.6882(4) 0.0207(17) Uani 1 1 d . . . C1 C 0.0565(12) 0.0997(5) 0.7171(4) 0.0173(16) Uani 1 1 d U . . C15 C 0.4455(12) 0.3801(5) 0.7721(4) 0.0162(16) Uani 1 1 d U . . C17 C 0.7742(12) 0.4683(5) 0.7690(4) 0.0177(16) Uani 1 1 d . . . H17 H 0.8331 0.4231 0.7426 0.021 Uiso 1 1 calc R . . C6 C -0.3652(12) -0.0729(5) 0.7214(4) 0.0203(17) Uani 1 1 d . . . H6 H -0.5007 -0.0803 0.7387 0.024 Uiso 1 1 calc R . . C14 C -0.2088(13) 0.3626(5) 0.5721(4) 0.0195(17) Uani 1 1 d . . . H14 H -0.2820 0.3543 0.6162 0.023 Uiso 1 1 calc R . . C10 C 0.0945(13) 0.3476(5) 0.5021(4) 0.0223(18) Uani 1 1 d . . . H10 H 0.2290 0.3294 0.4981 0.027 Uiso 1 1 calc R . . C22 C 0.4045(12) 0.1829(5) 0.8552(4) 0.0190(17) Uani 1 1 d . . . C13 C -0.3013(12) 0.4000(5) 0.5143(4) 0.0169(16) Uani 1 1 d . . . H13 H -0.4361 0.4180 0.5179 0.020 Uiso 1 1 calc R . . C3 C 0.0365(13) -0.0538(5) 0.6723(4) 0.0208(17) Uani 1 1 d . . . H3 H 0.1731 -0.0474 0.6560 0.025 Uiso 1 1 calc R . . C19 C 0.8029(14) 0.6076(5) 0.8252(4) 0.0225(18) Uani 1 1 d . . . C4 C -0.0725(13) -0.1318(5) 0.6637(4) 0.0221(18) Uani 1 1 d . . . H4 H -0.0105 -0.1788 0.6413 0.027 Uiso 1 1 calc R . . C2 C -0.0591(12) 0.0161(5) 0.7058(4) 0.0182(16) Uani 1 1 d . . . C21 C 0.4880(12) 0.5268(5) 0.8299(4) 0.0186(16) Uani 1 1 d . . . H21 H 0.3502 0.5207 0.8451 0.022 Uiso 1 1 calc R . . C28 C 0.4027(12) 0.1501(5) 0.9883(4) 0.0201(17) Uani 1 1 d . . . H28 H 0.2707 0.1711 0.9915 0.024 Uiso 1 1 calc R . . C23 C 0.5037(12) 0.1494(5) 0.9217(4) 0.0173(16) Uani 1 1 d . . . C7 C -0.2603(13) 0.0064(5) 0.7296(4) 0.0205(17) Uani 1 1 d . . . H7 H -0.3251 0.0532 0.7512 0.025 Uiso 1 1 calc R . . C18 C 0.8895(12) 0.5431(5) 0.7867(4) 0.0211(17) Uani 1 1 d . . . H18 H 1.0277 0.5494 0.7721 0.025 Uiso 1 1 calc R . . C20 C 0.6020(13) 0.6019(5) 0.8478(4) 0.0223(17) Uani 1 1 d . . . H20 H 0.5444 0.6473 0.8743 0.027 Uiso 1 1 calc R . . C25 C 0.7881(13) 0.0896(5) 0.9787(4) 0.0215(17) Uani 1 1 d . . . H25 H 0.9207 0.0693 0.9755 0.026 Uiso 1 1 calc R . . C27 C 0.4932(13) 0.1204(5) 1.0505(4) 0.0234(18) Uani 1 1 d . . . H27 H 0.4241 0.1207 1.0961 0.028 Uiso 1 1 calc R . . C11 C 0.0053(12) 0.3844(5) 0.4434(4) 0.0207(17) Uani 1 1 d . . . H11 H 0.0769 0.3916 0.3989 0.025 Uiso 1 1 calc R . . C30 C 0.0970(13) 0.3992(6) 0.9568(5) 0.029(2) Uani 1 1 d . . . H30A H 0.0488 0.4513 0.9376 0.043 Uiso 1 1 calc R . . H30B H 0.2226 0.3850 0.9318 0.043 Uiso 1 1 calc R . . H30C H 0.1237 0.4075 1.0095 0.043 Uiso 1 1 calc R . . C29 C -0.3029(14) 0.3688(5) 0.9763(5) 0.028(2) Uani 1 1 d . . . H29A H -0.4269 0.3315 0.9713 0.041 Uiso 1 1 calc R . . H29B H -0.3191 0.4197 0.9488 0.041 Uiso 1 1 calc R . . H29C H -0.2787 0.3849 1.0282 0.041 Uiso 1 1 calc R . . C31 C 0.8354(15) 0.1007(7) 0.5244(5) 0.040(2) Uani 1 1 d . . . H31A H 0.9401 0.0789 0.5555 0.060 Uiso 1 1 calc R . . H31B H 0.8763 0.1588 0.5120 0.060 Uiso 1 1 calc R . . H31C H 0.8192 0.0651 0.4793 0.060 Uiso 1 1 calc R . . C32 C 0.4578(17) 0.1448(6) 0.5036(5) 0.040(3) Uani 1 1 d . . . H32A H 0.5304 0.1970 0.4886 0.060 Uiso 1 1 calc R . . H32B H 0.3238 0.1578 0.5227 0.060 Uiso 1 1 calc R . . H32C H 0.4409 0.1048 0.4613 0.060 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 I1 0.0303(3) 0.0208(3) 0.0283(3) 0.0011(2) -0.0023(2) -0.0055(2) I2 0.0306(3) 0.0240(3) 0.0313(3) -0.0003(2) -0.0025(3) -0.0083(2) I3 0.0231(3) 0.0211(3) 0.0181(2) 0.0051(2) -0.0059(2) 0.0022(2) I4 0.0244(3) 0.0194(3) 0.0198(2) 0.00570(19) -0.0066(2) 0.0034(2) Cu5 0.0160(5) 0.0140(4) 0.0149(4) 0.0023(3) -0.0014(4) 0.0025(4) Cu6 0.0158(5) 0.0140(4) 0.0156(4) 0.0023(3) -0.0016(4) 0.0027(4) S7 0.0238(11) 0.0217(10) 0.0198(9) 0.0010(8) -0.0019(8) 0.0042(9) S8 0.0298(12) 0.0232(10) 0.0227(10) 0.0004(8) -0.0003(9) 0.0079(9) O5 0.022(3) 0.017(3) 0.021(3) 0.002(2) 0.000(2) 0.002(2) C8 0.019(4) 0.016(4) 0.018(4) 0.003(3) -0.006(3) -0.001(3) O10 0.026(3) 0.018(3) 0.017(3) 0.001(2) -0.001(2) 0.000(2) O4 0.018(3) 0.021(3) 0.020(3) 0.004(2) -0.002(2) 0.007(2) O7 0.020(3) 0.019(3) 0.019(3) 0.007(2) -0.004(2) 0.006(2) O8 0.022(3) 0.019(3) 0.016(3) 0.000(2) -0.002(2) 0.010(2) O6 0.021(3) 0.020(3) 0.029(3) -0.003(2) -0.001(3) -0.002(2) O9 0.021(3) 0.021(3) 0.025(3) -0.001(2) 0.000(2) -0.001(2) C24 0.023(4) 0.016(4) 0.015(4) 0.006(3) -0.002(3) -0.002(3) O1 0.020(3) 0.022(3) 0.017(3) 0.001(2) -0.001(2) 0.007(2) C12 0.017(4) 0.016(4) 0.017(4) 0.005(3) -0.004(3) 0.004(3) C16 0.018(4) 0.020(4) 0.012(3) -0.001(3) -0.006(3) 0.001(3) O3 0.022(3) 0.021(3) 0.024(3) 0.005(2) -0.001(2) 0.010(2) O2 0.024(3) 0.024(3) 0.015(3) -0.001(2) -0.002(2) 0.007(2) C9 0.017(4) 0.012(3) 0.022(4) 0.004(3) -0.005(3) 0.000(3) C26 0.025(4) 0.015(4) 0.015(4) 0.000(3) -0.006(3) -0.006(3) C5 0.031(5) 0.011(4) 0.021(4) 0.002(3) -0.008(3) -0.002(3) C1 0.020(3) 0.019(3) 0.013(3) 0.004(3) -0.010(3) 0.003(3) C15 0.015(3) 0.020(3) 0.014(3) 0.007(3) -0.005(3) 0.004(3) C17 0.019(4) 0.013(4) 0.022(4) 0.001(3) 0.006(3) 0.007(3) C6 0.013(4) 0.025(4) 0.023(4) -0.003(3) -0.002(3) 0.005(3) C14 0.023(4) 0.017(4) 0.019(4) 0.006(3) -0.003(3) 0.004(3) C10 0.024(5) 0.023(4) 0.021(4) 0.004(3) 0.006(3) 0.005(4) C22 0.015(4) 0.019(4) 0.023(4) 0.002(3) -0.007(3) -0.002(3) C13 0.014(4) 0.018(4) 0.019(4) 0.004(3) 0.000(3) 0.002(3) C3 0.017(4) 0.023(4) 0.021(4) 0.005(3) -0.005(3) -0.003(3) C19 0.035(5) 0.017(4) 0.015(4) 0.005(3) -0.011(4) -0.007(4) C4 0.032(5) 0.016(4) 0.019(4) -0.002(3) 0.004(4) 0.002(4) C2 0.019(4) 0.016(4) 0.019(4) 0.007(3) -0.005(3) -0.003(3) C21 0.014(4) 0.025(4) 0.017(4) 0.007(3) 0.000(3) 0.001(3) C28 0.015(4) 0.025(4) 0.021(4) 0.003(3) 0.000(3) -0.001(3) C23 0.016(4) 0.016(4) 0.020(4) -0.002(3) -0.006(3) 0.001(3) C7 0.022(4) 0.025(4) 0.016(4) 0.004(3) -0.001(3) 0.009(4) C18 0.015(4) 0.023(4) 0.025(4) -0.002(3) -0.004(3) -0.003(3) C20 0.023(5) 0.021(4) 0.023(4) -0.002(3) -0.001(3) 0.001(3) C25 0.023(4) 0.017(4) 0.026(4) 0.005(3) -0.004(4) 0.007(3) C27 0.023(5) 0.031(5) 0.017(4) 0.002(3) 0.005(3) 0.005(4) C11 0.020(4) 0.022(4) 0.021(4) 0.001(3) 0.007(3) 0.009(3) C30 0.022(5) 0.036(5) 0.027(4) 0.000(4) 0.005(4) -0.005(4) C29 0.037(5) 0.020(4) 0.024(4) -0.007(3) 0.009(4) 0.003(4) C31 0.037(6) 0.061(7) 0.023(5) -0.002(4) 0.006(4) 0.010(5) C32 0.052(7) 0.043(6) 0.026(5) -0.009(4) -0.009(5) 0.025(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C5 2.090(8) . ? I2 C19 2.108(8) . ? I3 C26 2.103(7) . ? I4 C12 2.118(7) . ? Cu5 Cu6 2.6358(13) . ? Cu5 O5 1.954(5) . ? Cu5 O7 1.968(5) . ? Cu5 O9 1.991(6) . ? Cu5 O3 1.978(5) . ? Cu5 O2 2.171(5) . ? Cu6 O10 1.962(5) . ? Cu6 O4 1.949(5) . ? Cu6 O8 1.972(5) . ? Cu6 O6 1.970(6) . ? Cu6 O1 2.160(5) . ? S7 O1 1.509(5) . ? S7 C30 1.784(9) . ? S7 C29 1.779(8) . ? S8 O2 1.510(6) . ? S8 C31 1.794(10) . ? S8 C32 1.761(9) . ? O5 C15 1.269(9) . ? C8 O4 1.265(9) . ? C8 O3 1.260(9) . ? C8 C9 1.512(10) . ? O10 C1 1.262(9) . ? O7 C22 1.249(9) . ? O8 C22 1.265(9) . ? O6 C15 1.266(9) . ? O9 C1 1.266(9) . ? C24 C23 1.369(11) . ? C24 C25 1.391(10) . ? C12 C13 1.383(10) . ? C12 C11 1.370(11) . ? C16 C15 1.505(11) . ? C16 C17 1.395(11) . ? C16 C21 1.387(11) . ? C9 C14 1.382(11) . ? C9 C10 1.385(10) . ? C26 C25 1.389(11) . ? C26 C27 1.375(12) . ? C5 C6 1.385(11) . ? C5 C4 1.398(12) . ? C1 C2 1.494(10) . ? C17 C18 1.395(11) . ? C6 C7 1.400(11) . ? C14 C13 1.388(10) . ? C10 C11 1.387(11) . ? C22 C23 1.506(10) . ? C3 C4 1.394(11) . ? C3 C2 1.424(11) . ? C19 C18 1.371(11) . ? C19 C20 1.386(12) . ? C2 C7 1.398(11) . ? C21 C20 1.394(11) . ? C28 C23 1.390(11) . ? C28 C27 1.393(11) . ? 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 Cu5 Cu6 83.07(16) . . ? O5 Cu5 O7 90.9(2) . . ? O5 Cu5 O9 169.4(2) . . ? O5 Cu5 O3 89.6(2) . . ? O5 Cu5 O2 98.8(2) . . ? O7 Cu5 Cu6 82.18(16) . . ? O7 Cu5 O9 89.0(2) . . ? O7 Cu5 O3 167.2(2) . . ? O7 Cu5 O2 98.4(2) . . ? O9 Cu5 Cu6 86.40(16) . . ? O9 Cu5 O2 91.7(2) . . ? O3 Cu5 Cu6 85.24(16) . . ? O3 Cu5 O9 88.1(2) . . ? O3 Cu5 O2 94.1(2) . . ? O2 Cu5 Cu6 178.05(16) . . ? O10 Cu6 Cu5 82.09(16) . . ? O10 Cu6 O8 89.5(2) . . ? O10 Cu6 O6 167.5(2) . . ? O10 Cu6 O1 98.8(2) . . ? O4 Cu6 Cu5 83.33(16) . . ? O4 Cu6 O10 91.4(2) . . ? O4 Cu6 O8 168.7(2) . . ? O4 Cu6 O6 89.4(2) . . ? O4 Cu6 O1 101.1(2) . . ? O8 Cu6 Cu5 85.64(15) . . ? O8 Cu6 O1 89.9(2) . . ? O6 Cu6 Cu5 85.61(17) . . ? O6 Cu6 O8 87.3(2) . . ? O6 Cu6 O1 93.3(2) . . ? O1 Cu6 Cu5 175.43(14) . . ? O1 S7 C30 106.0(4) . . ? O1 S7 C29 103.5(4) . . ? C29 S7 C30 97.4(4) . . ? O2 S8 C31 103.6(4) . . ? O2 S8 C32 105.7(4) . . ? C32 S8 C31 96.5(5) . . ? C15 O5 Cu5 124.5(5) . . ? O4 C8 C9 116.4(7) . . ? O3 C8 O4 126.0(7) . . ? O3 C8 C9 117.5(7) . . ? C1 O10 Cu6 125.1(5) . . ? C8 O4 Cu6 124.3(5) . . ? C22 O7 Cu5 124.7(5) . . ? C22 O8 Cu6 120.1(5) . . ? C15 O6 Cu6 120.6(5) . . ? C1 O9 Cu5 118.3(5) . . ? C23 C24 C25 121.0(7) . . ? S7 O1 Cu6 121.1(3) . . ? C13 C12 I4 117.9(5) . . ? C11 C12 I4 118.8(5) . . ? C11 C12 C13 123.3(7) . . ? C17 C16 C15 119.6(7) . . ? C21 C16 C15 120.6(7) . . ? C21 C16 C17 119.8(7) . . ? C8 O3 Cu5 120.7(5) . . ? S8 O2 Cu5 123.8(3) . . ? C14 C9 C8 120.0(7) . . ? C14 C9 C10 119.8(7) . . ? C10 C9 C8 120.1(7) . . ? C25 C26 I3 118.5(6) . . ? C27 C26 I3 120.0(6) . . ? C27 C26 C25 121.5(7) . . ? C6 C5 I1 119.7(6) . . ? C6 C5 C4 120.7(7) . . ? C4 C5 I1 119.5(6) . . ? O10 C1 O9 126.7(7) . . ? O10 C1 C2 116.8(7) . . ? O9 C1 C2 116.5(7) . . ? O5 C15 C16 117.0(7) . . ? O6 C15 O5 125.6(7) . . ? O6 C15 C16 117.3(7) . . ? C18 C17 C16 119.1(7) . . ? C5 C6 C7 120.5(7) . . ? C9 C14 C13 121.2(7) . . ? C9 C10 C11 120.1(7) . . ? O7 C22 O8 125.9(7) . . ? O7 C22 C23 117.9(7) . . ? O8 C22 C23 116.2(7) . . ? C12 C13 C14 117.1(7) . . ? C4 C3 C2 119.3(7) . . ? C18 C19 I2 119.3(6) . . ? C18 C19 C20 122.5(8) . . ? C20 C19 I2 118.2(6) . . ? C3 C4 C5 119.9(7) . . ? C3 C2 C1 120.2(7) . . ? C7 C2 C1 119.6(7) . . ? C7 C2 C3 120.2(7) . . ? C16 C21 C20 121.5(7) . . ? C23 C28 C27 120.6(7) . . ? C24 C23 C22 120.6(7) . . ? C24 C23 C28 119.5(7) . . ? C28 C23 C22 119.8(7) . . ? C2 C7 C6 119.3(7) . . ? C19 C18 C17 119.8(8) . . ? C19 C20 C21 117.3(7) . . ? C26 C25 C24 118.6(7) . . ? C26 C27 C28 118.8(7) . . ? C12 C11 C10 118.4(7) . . ? data_ilb2088_0m _database_code_depnum_ccdc_archive 'CCDC 912206' #TrackingRef '3_EtOH.cif' _audit_creation_date 2013-01-07 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C32 H28 Cu2 I4 O10' _chemical_formula_sum 'C32 H28 Cu2 I4 O10' _chemical_formula_weight 1207.22 _chemical_melting_point ? 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 12.196(2) _cell_length_b 13.011(2) _cell_length_c 13.015(2) _cell_angle_alpha 74.517(7) _cell_angle_beta 68.073(7) _cell_angle_gamma 87.380(8) _cell_volume 1842.9(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9252 _cell_measurement_temperature 100 _cell_measurement_theta_max 26.11 _cell_measurement_theta_min 2.50 _exptl_absorpt_coefficient_mu 4.557 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1124 before and 0.0820 after correction. The Ratio of minimum to maximum transmission is 0.8039. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light blue' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 2.176 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1140 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0679 _diffrn_reflns_av_unetI/netI 0.0615 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 37498 _diffrn_reflns_theta_full 27.51 _diffrn_reflns_theta_max 27.51 _diffrn_reflns_theta_min 1.63 _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 5607 _reflns_number_total 8303 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 1.644 _refine_diff_density_min -1.065 _refine_diff_density_rms 0.157 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 446 _refine_ls_number_reflns 8303 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0688 _refine_ls_R_factor_gt 0.0411 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0350P)^2^+2.5459P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0976 _refine_ls_wR_factor_ref 0.1093 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H7 of C7, H14 of C14, H3 of C3, H29 of C29, H26 of C26, {H30a,H30b} of C30, H13 of C13, H28 of C28, H17 of C17, {H32a,H32b,H32c,H32d} of C32, H4 of C4, H21 of C21, H11 of C11, H10 of C10, H18 of C18, H20 of C20, H25 of C25, H6 of C6 At 1.5 times of: {H34a,H34b,H34c} of C34, H10a of O10, {H33d,H33e,H33f} of C33A, H9 of O9, {H33a,H33b,H33c} of C33 2. Restrained distances O9-H9 0.85 with sigma of 0.01 O10-H10a 0.85 with sigma of 0.01 C30-H9 1.884885 with sigma of 0.02 C32-H10a 1.889448 with sigma of 0.02 3. Uiso/Uaniso restraints and constraints Uanis(C33) = Uanis(C33A) 4. Others Sof(H32a)=Sof(H32b)=1-Sof(H32b)=1-Sof(H32b)=Sof(C33)=Sof(H33a)=Sof(H33b)= Sof(H33c)=1-Sof(H32b)=1-Sof(H32b)=1-Sof(H32b)=1-Sof(H32b) 5.a Secondary CH2 refined with riding coordinates: C30(H30a,H30b), C32(H32a,H32b), C32(H32c,H32d) 5.b Aromatic/amide H refined with riding coordinates: C14(H14), C21(H21), C6(H6), C20(H20), C3(H3), C29(H29), C7(H7), C18(H18), C17(H17), C28(H28), C11(H11), C4(H4), C10(H10), C13(H13), C26(H26), C25(H25) 5.c Idealised Me refined as rotating group: C34(H34a,H34b,H34c), C33(H33a,H33b,H33c), C33A(H33d,H33e,H33f) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 I1 I 1.18225(3) -0.11849(3) 0.06599(3) 0.02890(11) Uani 1 1 d . . . I4 I 0.81164(3) 1.10164(3) 0.44019(3) 0.03010(11) Uani 1 1 d . . . I3 I 0.40977(3) 0.09743(3) 0.85164(3) 0.04377(13) Uani 1 1 d . . . I2 I 1.58558(3) 0.88341(3) -0.34399(3) 0.04878(14) Uani 1 1 d . . . Cu2 Cu 1.06168(5) 0.47316(4) 0.31349(5) 0.01601(14) Uani 1 1 d . . . Cu1 Cu 0.93054(5) 0.51125(4) 0.19273(5) 0.01559(14) Uani 1 1 d . . . O1 O 1.0242(3) 0.6162(2) 0.3313(3) 0.0216(7) Uani 1 1 d . . . O9 O 1.1694(3) 0.4435(3) 0.4131(3) 0.0219(7) Uani 1 1 d D . . H9 H 1.157(2) 0.483(3) 0.457(3) 0.033 Uiso 1 1 d D . . O2 O 0.8824(3) 0.6311(2) 0.2602(3) 0.0252(8) Uani 1 1 d . . . O3 O 1.0690(3) 0.5983(2) 0.0751(3) 0.0222(8) Uani 1 1 d . . . O7 O 0.9069(3) 0.4195(3) 0.4399(3) 0.0239(8) Uani 1 1 d . . . O5 O 1.0048(3) 0.3842(2) 0.1456(3) 0.0219(8) Uani 1 1 d . . . C1 C 0.9417(4) 0.6644(4) 0.3069(4) 0.0164(10) Uani 1 1 d . . . C15 C 1.0547(4) 0.3163(4) 0.2025(4) 0.0165(10) Uani 1 1 d . . . C14 C 1.3789(5) 0.6711(4) -0.0109(5) 0.0332(13) Uani 1 1 d . . . H14 H 1.3899 0.6390 0.0590 0.040 Uiso 1 1 calc R . . O4 O 1.1915(3) 0.5345(3) 0.1656(3) 0.0247(8) Uani 1 1 d . . . O8 O 0.8087(3) 0.4146(3) 0.3266(3) 0.0241(8) Uani 1 1 d . . . C21 C 1.1472(4) 0.1419(4) 0.2227(4) 0.0253(12) Uani 1 1 d . . . H21 H 1.1716 0.1583 0.2781 0.030 Uiso 1 1 calc R . . C6 C 0.9240(4) 0.8898(4) 0.4428(4) 0.0237(11) Uani 1 1 d . . . H6 H 0.9507 0.9080 0.4960 0.028 Uiso 1 1 calc R . . C24 C 0.7195(4) 0.3268(4) 0.5249(4) 0.0200(11) Uani 1 1 d . . . C22 C 1.0848(4) 0.2146(3) 0.1708(4) 0.0183(10) Uani 1 1 d . . . C12 C 1.4524(5) 0.7810(4) -0.2050(4) 0.0332(13) Uani 1 1 d . . . C2 C 0.9128(4) 0.7676(4) 0.3372(4) 0.0176(10) Uani 1 1 d . . . C19 C 1.1395(4) 0.0242(4) 0.1133(4) 0.0223(11) Uani 1 1 d . . . C20 C 1.1747(4) 0.0464(4) 0.1957(4) 0.0277(12) Uani 1 1 d . . . H20 H 1.2169 -0.0034 0.2325 0.033 Uiso 1 1 calc R . . C3 C 0.8446(4) 0.8382(4) 0.2881(4) 0.0234(11) Uani 1 1 d . . . H3 H 0.8170 0.8199 0.2356 0.028 Uiso 1 1 calc R . . C27 C 0.5404(5) 0.1992(4) 0.7124(4) 0.0284(12) Uani 1 1 d . . . C29 C 0.7311(4) 0.2915(4) 0.6306(4) 0.0249(11) Uani 1 1 d . . . H29 H 0.8009 0.3109 0.6389 0.030 Uiso 1 1 calc R . . C9 C 1.2707(4) 0.6543(4) -0.0199(4) 0.0204(11) Uani 1 1 d . . . C7 C 0.9511(4) 0.7945(4) 0.4149(4) 0.0224(11) Uani 1 1 d . . . H7 H 0.9966 0.7466 0.4493 0.027 Uiso 1 1 calc R . . C5 C 0.8571(4) 0.9591(4) 0.3920(4) 0.0251(12) Uani 1 1 d . . . C18 C 1.0774(4) 0.0960(4) 0.0594(4) 0.0256(12) Uani 1 1 d . . . H18 H 1.0536 0.0800 0.0035 0.031 Uiso 1 1 calc R . . O6 O 1.0785(3) 0.3321(3) 0.2835(3) 0.0263(8) Uani 1 1 d . . . C17 C 1.0508(4) 0.1914(4) 0.0885(4) 0.0227(11) Uani 1 1 d . . . H17 H 1.0088 0.2415 0.0518 0.027 Uiso 1 1 calc R . . C28 C 0.6411(4) 0.2280(4) 0.7239(4) 0.0277(12) Uani 1 1 d . . . H28 H 0.6491 0.2042 0.7963 0.033 Uiso 1 1 calc R . . C11 C 1.3479(4) 0.7633(4) -0.2166(4) 0.0263(12) Uani 1 1 d . . . H11 H 1.3381 0.7937 -0.2874 0.032 Uiso 1 1 calc R . . C23 C 0.8186(4) 0.3920(4) 0.4226(4) 0.0201(11) Uani 1 1 d . . . C4 C 0.8173(5) 0.9339(4) 0.3149(4) 0.0277(12) Uani 1 1 d . . . H4 H 0.7716 0.9819 0.2808 0.033 Uiso 1 1 calc R . . C10 C 1.2564(4) 0.7001(4) -0.1227(4) 0.0233(11) Uani 1 1 d . . . H10 H 1.1834 0.6883 -0.1294 0.028 Uiso 1 1 calc R . . C13 C 1.4699(5) 0.7341(5) -0.1032(5) 0.0388(15) Uani 1 1 d . . . H13 H 1.5435 0.7454 -0.0973 0.047 Uiso 1 1 calc R . . C26 C 0.5265(4) 0.2353(4) 0.6079(5) 0.0311(13) Uani 1 1 d . . . H26 H 0.4559 0.2163 0.6006 0.037 Uiso 1 1 calc R . . C8 C 1.1697(4) 0.5908(4) 0.0807(4) 0.0199(11) Uani 1 1 d . . . C25 C 0.6158(4) 0.2992(4) 0.5142(4) 0.0264(12) Uani 1 1 d . . . H25 H 0.6066 0.3244 0.4425 0.032 Uiso 1 1 calc R . . O10 O 0.8287(3) 0.5492(3) 0.0864(3) 0.0207(7) Uani 1 1 d D A . H10A H 0.875(2) 0.570(3) 0.0167(14) 0.031 Uiso 1 1 d D . . C30 C 1.2936(5) 0.4307(5) 0.3584(5) 0.0458(16) Uani 1 1 d D . . H30A H 1.3031 0.3772 0.3145 0.055 Uiso 1 1 calc R . . H30B H 1.3313 0.4995 0.3027 0.055 Uiso 1 1 calc R . . C34 C 1.3548(6) 0.3980(6) 0.4350(7) 0.068(2) Uani 1 1 d . . . H34A H 1.4398 0.3985 0.3905 0.102 Uiso 1 1 calc R . . H34B H 1.3255 0.3257 0.4840 0.102 Uiso 1 1 calc R . . H34C H 1.3413 0.4474 0.4831 0.102 Uiso 1 1 calc R . . C32 C 0.7270(5) 0.6108(5) 0.1066(6) 0.0524(18) Uani 1 1 d D . . H32A H 0.7460 0.6786 0.1190 0.063 Uiso 0.685(8) 1 calc PR A 1 H32B H 0.7059 0.6288 0.0376 0.063 Uiso 0.685(8) 1 calc PR A 1 H32C H 0.6914 0.5995 0.1910 0.063 Uiso 0.315(8) 1 calc PR A 2 H32D H 0.7581 0.6863 0.0738 0.063 Uiso 0.315(8) 1 calc PR A 2 C33 C 0.6296(7) 0.5565(7) 0.2021(8) 0.045(2) Uani 0.685(8) 1 d P A 1 H33A H 0.6113 0.4887 0.1907 0.067 Uiso 0.685(8) 1 calc PR A 1 H33B H 0.5610 0.6005 0.2110 0.067 Uiso 0.685(8) 1 calc PR A 1 H33C H 0.6485 0.5421 0.2713 0.067 Uiso 0.685(8) 1 calc PR A 1 C33A C 0.6377(16) 0.6053(15) 0.0751(18) 0.045(2) Uani 0.315(8) 1 d P A 2 H33D H 0.6237 0.6771 0.0355 0.067 Uiso 0.315(8) 1 calc PR A 2 H33E H 0.5666 0.5756 0.1432 0.067 Uiso 0.315(8) 1 calc PR A 2 H33F H 0.6559 0.5592 0.0230 0.067 Uiso 0.315(8) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0353(2) 0.01936(18) 0.0301(2) -0.00943(15) -0.00832(16) 0.00334(15) I4 0.0346(2) 0.01969(19) 0.0333(2) -0.01083(15) -0.00728(17) 0.00308(15) I3 0.0295(2) 0.0483(3) 0.0336(2) 0.00956(18) -0.00280(17) -0.00745(18) I2 0.0327(2) 0.0556(3) 0.0372(2) 0.0061(2) -0.00107(19) -0.0134(2) Cu2 0.0192(3) 0.0145(3) 0.0149(3) -0.0045(2) -0.0067(2) 0.0018(2) Cu1 0.0185(3) 0.0138(3) 0.0144(3) -0.0037(2) -0.0062(2) 0.0013(2) O1 0.034(2) 0.0133(16) 0.0225(18) -0.0059(14) -0.0150(16) 0.0014(15) O9 0.0203(19) 0.027(2) 0.024(2) -0.0117(15) -0.0109(15) 0.0047(15) O2 0.031(2) 0.0201(18) 0.033(2) -0.0142(16) -0.0179(17) 0.0081(15) O3 0.025(2) 0.0200(18) 0.0222(19) -0.0007(14) -0.0121(15) -0.0034(14) O7 0.026(2) 0.0233(19) 0.0196(18) -0.0006(14) -0.0081(15) -0.0076(15) O5 0.032(2) 0.0162(17) 0.0222(19) -0.0052(14) -0.0158(16) 0.0039(15) C1 0.016(3) 0.017(2) 0.011(2) 0.0012(19) -0.003(2) -0.0012(19) C15 0.012(2) 0.017(2) 0.019(3) -0.004(2) -0.005(2) -0.0008(19) C14 0.031(3) 0.039(3) 0.026(3) -0.002(2) -0.010(3) -0.003(3) O4 0.0218(19) 0.0278(19) 0.0191(19) 0.0005(15) -0.0063(15) 0.0005(15) O8 0.0226(19) 0.030(2) 0.0146(18) 0.0011(15) -0.0063(15) -0.0032(15) C21 0.032(3) 0.028(3) 0.020(3) -0.010(2) -0.012(2) 0.004(2) C6 0.028(3) 0.023(3) 0.022(3) -0.007(2) -0.011(2) 0.002(2) C24 0.023(3) 0.016(2) 0.020(3) -0.005(2) -0.008(2) 0.005(2) C22 0.024(3) 0.013(2) 0.015(2) -0.0008(19) -0.006(2) -0.003(2) C12 0.028(3) 0.033(3) 0.027(3) -0.002(2) 0.000(2) -0.005(2) C2 0.014(2) 0.018(2) 0.019(3) -0.004(2) -0.005(2) -0.0017(19) C19 0.024(3) 0.014(2) 0.025(3) -0.004(2) -0.006(2) -0.001(2) C20 0.027(3) 0.023(3) 0.030(3) -0.005(2) -0.010(2) 0.009(2) C3 0.022(3) 0.025(3) 0.025(3) -0.009(2) -0.010(2) 0.001(2) C27 0.027(3) 0.028(3) 0.021(3) 0.000(2) -0.003(2) 0.001(2) C29 0.024(3) 0.025(3) 0.026(3) -0.006(2) -0.010(2) -0.001(2) C9 0.025(3) 0.016(2) 0.017(3) -0.003(2) -0.005(2) 0.001(2) C7 0.025(3) 0.022(3) 0.020(3) -0.005(2) -0.009(2) 0.002(2) C5 0.029(3) 0.014(2) 0.027(3) -0.006(2) -0.005(2) 0.002(2) C18 0.032(3) 0.020(3) 0.025(3) -0.003(2) -0.013(2) -0.004(2) O6 0.037(2) 0.0221(18) 0.029(2) -0.0126(15) -0.0189(17) 0.0087(16) C17 0.027(3) 0.022(3) 0.022(3) -0.006(2) -0.013(2) 0.004(2) C28 0.035(3) 0.026(3) 0.018(3) 0.001(2) -0.010(2) 0.001(2) C11 0.028(3) 0.024(3) 0.021(3) -0.002(2) -0.005(2) 0.002(2) C23 0.024(3) 0.014(2) 0.022(3) -0.008(2) -0.005(2) 0.004(2) C4 0.031(3) 0.023(3) 0.027(3) -0.006(2) -0.010(2) 0.004(2) C10 0.026(3) 0.019(3) 0.024(3) -0.007(2) -0.008(2) 0.001(2) C13 0.020(3) 0.054(4) 0.034(3) 0.000(3) -0.008(3) -0.002(3) C26 0.019(3) 0.033(3) 0.037(3) -0.004(3) -0.009(2) -0.001(2) C8 0.025(3) 0.016(2) 0.020(3) -0.009(2) -0.009(2) 0.005(2) C25 0.028(3) 0.025(3) 0.023(3) -0.002(2) -0.009(2) -0.002(2) O10 0.0203(19) 0.0225(18) 0.0187(18) -0.0047(15) -0.0076(15) 0.0030(14) C30 0.037(4) 0.061(4) 0.051(4) -0.022(3) -0.026(3) 0.016(3) C34 0.063(5) 0.059(5) 0.081(6) -0.015(4) -0.031(4) 0.020(4) C32 0.032(4) 0.049(4) 0.075(5) -0.019(4) -0.019(4) 0.019(3) C33 0.027(4) 0.039(5) 0.064(6) -0.015(4) -0.012(4) 0.003(4) C33A 0.027(4) 0.039(5) 0.064(6) -0.015(4) -0.012(4) 0.003(4) _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 I1 C19 2.093(5) . ? I4 C5 2.099(5) . ? I3 C27 2.081(5) . ? I2 C12 2.098(5) . ? Cu2 Cu1 2.5813(8) . ? Cu2 O1 1.949(3) . ? Cu2 O9 2.125(3) . ? Cu2 O7 1.986(3) . ? Cu2 O4 1.966(3) . ? Cu2 O6 1.962(3) . ? Cu1 O2 1.952(3) . ? Cu1 O3 1.949(3) . ? Cu1 O5 1.980(3) . ? Cu1 O8 1.973(3) . ? Cu1 O10 2.135(3) . ? O1 C1 1.257(5) . ? O9 C30 1.436(6) . ? O2 C1 1.256(5) . ? O3 C8 1.255(5) . ? O7 C23 1.265(5) . ? O5 C15 1.280(5) . ? C1 C2 1.489(6) . ? C15 C22 1.480(6) . ? C15 O6 1.260(5) . ? C14 C9 1.399(7) . ? C14 C13 1.382(7) . ? O4 C8 1.265(5) . ? O8 C23 1.255(5) . ? C21 C22 1.381(7) . ? C21 C20 1.373(7) . ? C6 C7 1.375(7) . ? C6 C5 1.390(7) . ? C24 C29 1.388(6) . ? C24 C23 1.497(6) . ? C24 C25 1.395(7) . ? C22 C17 1.388(6) . ? C12 C11 1.375(7) . ? C12 C13 1.392(7) . ? C2 C3 1.400(6) . ? C2 C7 1.385(6) . ? C19 C20 1.393(7) . ? C19 C18 1.386(7) . ? C3 C4 1.374(7) . ? C27 C28 1.372(7) . ? C27 C26 1.387(7) . ? C29 C28 1.383(6) . ? C9 C10 1.384(6) . ? C9 C8 1.491(6) . ? C5 C4 1.381(7) . ? C18 C17 1.382(7) . ? C11 C10 1.394(6) . ? C26 C25 1.384(7) . ? O10 C32 1.425(6) . ? C30 C34 1.426(8) . ? C32 C33 1.400(10) . ? C32 C33A 1.309(19) . ? 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 Cu2 Cu1 84.04(9) . . ? O1 Cu2 O9 95.36(13) . . ? O1 Cu2 O7 88.08(14) . . ? O1 Cu2 O4 90.12(14) . . ? O1 Cu2 O6 170.01(14) . . ? O9 Cu2 Cu1 179.40(9) . . ? O7 Cu2 Cu1 81.82(10) . . ? O7 Cu2 O9 98.21(13) . . ? O4 Cu2 Cu1 84.40(10) . . ? O4 Cu2 O9 95.57(13) . . ? O4 Cu2 O7 166.21(14) . . ? O6 Cu2 Cu1 86.10(10) . . ? O6 Cu2 O9 94.50(13) . . ? O6 Cu2 O7 88.95(14) . . ? O6 Cu2 O4 90.49(14) . . ? O2 Cu1 Cu2 84.15(10) . . ? O2 Cu1 O5 166.10(13) . . ? O2 Cu1 O8 91.05(14) . . ? O2 Cu1 O10 95.25(13) . . ? O3 Cu1 Cu2 83.93(10) . . ? O3 Cu1 O2 89.42(14) . . ? O3 Cu1 O5 88.50(13) . . ? O3 Cu1 O8 170.02(13) . . ? O3 Cu1 O10 93.14(13) . . ? O5 Cu1 Cu2 81.97(9) . . ? O5 Cu1 O10 98.59(13) . . ? O8 Cu1 Cu2 86.20(9) . . ? O8 Cu1 O5 88.66(14) . . ? O8 Cu1 O10 96.75(13) . . ? O10 Cu1 Cu2 177.00(9) . . ? C1 O1 Cu2 122.1(3) . . ? C30 O9 Cu2 119.3(3) . . ? C1 O2 Cu1 121.6(3) . . ? C8 O3 Cu1 122.5(3) . . ? C23 O7 Cu2 122.7(3) . . ? C15 O5 Cu1 123.6(3) . . ? O1 C1 C2 116.8(4) . . ? O2 C1 O1 124.6(4) . . ? O2 C1 C2 118.6(4) . . ? O5 C15 C22 117.6(4) . . ? O6 C15 O5 123.2(4) . . ? O6 C15 C22 119.2(4) . . ? C13 C14 C9 120.3(5) . . ? C8 O4 Cu2 120.4(3) . . ? C23 O8 Cu1 119.2(3) . . ? C20 C21 C22 121.3(5) . . ? C7 C6 C5 118.9(4) . . ? C29 C24 C23 120.2(4) . . ? C29 C24 C25 119.5(4) . . ? C25 C24 C23 120.3(4) . . ? C21 C22 C15 120.3(4) . . ? C21 C22 C17 119.3(5) . . ? C17 C22 C15 120.4(4) . . ? C11 C12 I2 118.4(4) . . ? C11 C12 C13 121.4(5) . . ? C13 C12 I2 120.2(4) . . ? C3 C2 C1 119.8(4) . . ? C7 C2 C1 121.1(4) . . ? C7 C2 C3 119.1(4) . . ? C20 C19 I1 120.3(4) . . ? C18 C19 I1 118.4(4) . . ? C18 C19 C20 121.2(5) . . ? C21 C20 C19 118.6(5) . . ? C4 C3 C2 120.7(5) . . ? C28 C27 I3 119.6(4) . . ? C28 C27 C26 120.5(5) . . ? C26 C27 I3 119.9(4) . . ? C28 C29 C24 120.0(5) . . ? C14 C9 C8 120.9(4) . . ? C10 C9 C14 119.3(4) . . ? C10 C9 C8 119.7(4) . . ? C6 C7 C2 120.9(5) . . ? C6 C5 I4 118.4(4) . . ? C4 C5 I4 120.2(4) . . ? C4 C5 C6 121.3(5) . . ? C17 C18 C19 118.8(5) . . ? C15 O6 Cu2 120.4(3) . . ? C18 C17 C22 120.7(5) . . ? C27 C28 C29 120.3(5) . . ? C12 C11 C10 118.9(5) . . ? O7 C23 C24 116.9(4) . . ? O8 C23 O7 124.9(4) . . ? O8 C23 C24 118.2(4) . . ? C3 C4 C5 119.1(5) . . ? C9 C10 C11 120.9(5) . . ? C14 C13 C12 119.2(5) . . ? C25 C26 C27 119.6(5) . . ? O3 C8 O4 124.9(4) . . ? O3 C8 C9 117.4(4) . . ? O4 C8 C9 117.7(4) . . ? C26 C25 C24 120.1(5) . . ? C32 O10 Cu1 125.3(4) . . ? C34 C30 O9 114.8(5) . . ? C33 C32 O10 112.2(6) . . ? C33A C32 O10 127.7(10) . . ? C33A C32 C33 70.8(10) . . ? data_hkl5 _database_code_depnum_ccdc_archive 'CCDC 912207' #TrackingRef '4_DMF_twin.cif' _audit_creation_date 2013-01-07 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C34 H30 Cu2 I4 N2 O10, 4(C3 H7 N O)' _chemical_formula_sum 'C46 H58 Cu2 I4 N6 O14' _chemical_formula_weight 1553.66 _chemical_melting_point ? 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/n 1' _space_group_name_Hall '-P 2yn' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.997(3) _cell_length_b 12.621(3) _cell_length_c 16.880(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.15(3) _cell_angle_gamma 90.00 _cell_volume 2753.0(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 1759 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 29.66 _cell_measurement_theta_min 2.42 _exptl_absorpt_coefficient_mu 3.082 _exptl_absorpt_correction_T_max 0.746072 _exptl_absorpt_correction_T_min 0.544531 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS 2007/2 (Sheldrick, G.M., 2007)' _exptl_crystal_colour 'clear dark blue' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 1.874 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1516 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.16 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0437 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 18555 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 27.40 _diffrn_reflns_theta_min 1.88 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.929 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 15548 _reflns_number_total 18635 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.23A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 1.237 _refine_diff_density_min -1.585 _refine_diff_density_rms 0.132 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 342 _refine_ls_number_reflns 18635 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0429 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0654P)^2^+1.1203P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1107 _refine_ls_wR_factor_ref 0.1149 _refine_special_details ; The crystal was a 3 component twin. Refinements were carried out against hklf 5 data. Please ignore the resulting checkcif alerts. For reflection statistics for each components see supplementary information table S2. 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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H16 of C16, H1S of C1S, H5 of C5, H2 of C2, H3 of C3, {H3SA,H3SB,H3SC} of C3S, H11S of C11S, {H22A,H22B,H22C} of C22S, H15 of C15, H21S of C21S, H12 of C12, {H2SA,H2SB,H2SC} of C2S, H6 of C6, H13 of C13, {H23A,H23B,H23C} of C23S At 1.5 times of: {H12D,H12E,H12F} of C12T, {H13D,H13E,H13F} of C13T, {H13A,H13B,H13C} of C13S, {H12A,H12B,H12C} of C12S 2. Uiso/Uaniso restraints and constraints Uanis(C13S) = Uanis(C13T) Uanis(C12S) = Uanis(C12T) 3. Others Sof(C12S)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13S)=Sof(H13A)=Sof(H13B)= Sof(H13C)=1-Sof(H12A)=1-Sof(H12A)=1-Sof(H12A)=1-Sof(H12A)=1-Sof(H12A)=1- Sof(H12A)=1-Sof(H12A)=1-Sof(H12A) 4.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C1S(H1S), C11S(H11S), C21S(H21S) 4.b Idealised Me refined as rotating group: C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC), C12S(H12A,H12B,H12C), C13S(H13A, H13B,H13C), C22S(H22A,H22B,H22C), C23S(H23A,H23B,H23C), C13T(H13D,H13E,H13F), C12T(H12D,H12E,H12F) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cu3 Cu 0.51385(3) 0.50044(3) 0.07758(2) 0.01131(8) Uani 1 1 d . . . I1 I 0.706090(16) 1.165463(17) -0.013441(14) 0.02616(7) Uani 1 1 d . . . I2 I -0.148916(17) 0.70995(2) 0.016898(16) 0.03667(8) Uani 1 1 d . . . O1 O 0.36756(15) 0.53951(17) 0.07348(12) 0.0173(4) Uani 1 1 d . . . O2 O 0.53000(16) 0.64706(15) -0.06695(12) 0.0158(4) Uani 1 1 d . . . O11 O 0.54987(16) 0.64963(16) 0.06680(12) 0.0177(5) Uani 1 1 d . . . O12 O 0.34464(15) 0.53892(17) -0.05974(12) 0.0173(5) Uani 1 1 d . . . C1 C 0.5885(2) 0.8028(2) -0.00268(18) 0.0145(6) Uani 1 1 d . . . C2 C 0.5886(2) 0.8670(3) 0.06325(18) 0.0203(7) Uani 1 1 d . . . H2 H 0.5656 0.8396 0.1107 0.024 Uiso 1 1 calc R . . C3 C 0.6219(2) 0.9712(3) 0.06098(19) 0.0213(7) Uani 1 1 d . . . H3 H 0.6217 1.0155 0.1065 0.026 Uiso 1 1 calc R . . C4 C 0.6554(2) 1.0097(2) -0.0088(2) 0.0205(7) Uani 1 1 d . . . C5 C 0.6587(2) 0.9449(3) -0.07529(19) 0.0202(7) Uani 1 1 d . . . H5 H 0.6848 0.9710 -0.1220 0.024 Uiso 1 1 calc R . . C6 C 0.6235(2) 0.8426(3) -0.07185(19) 0.0202(7) Uani 1 1 d . . . H6 H 0.6231 0.7982 -0.1174 0.024 Uiso 1 1 calc R . . C7 C 0.5529(2) 0.6908(2) 0.00000(18) 0.0156(6) Uani 1 1 d . . . C11 C 0.2033(2) 0.5828(2) 0.00986(17) 0.0156(6) Uani 1 1 d . . . C12 C 0.1583(3) 0.5840(3) 0.0814(2) 0.0253(7) Uani 1 1 d . . . H12 H 0.1977 0.5616 0.1291 0.030 Uiso 1 1 calc R . . C13 C 0.0571(3) 0.6174(3) 0.0837(2) 0.0289(8) Uani 1 1 d . . . H13 H 0.0269 0.6165 0.1325 0.035 Uiso 1 1 calc R . . C14 C 0.0012(2) 0.6517(3) 0.0154(2) 0.0259(8) Uani 1 1 d . . . C15 C 0.0429(3) 0.6491(3) -0.0576(2) 0.0285(8) Uani 1 1 d . . . H15 H 0.0026 0.6702 -0.1053 0.034 Uiso 1 1 calc R . . C16 C 0.1439(2) 0.6152(3) -0.0592(2) 0.0237(7) Uani 1 1 d . . . H16 H 0.1731 0.6141 -0.1085 0.028 Uiso 1 1 calc R . . C17 C 0.3133(2) 0.5503(2) 0.00755(17) 0.0132(6) Uani 1 1 d . . . C1S C 0.4830(2) 0.4758(2) 0.25050(17) 0.0173(7) Uani 1 1 d . . . H1S H 0.4149 0.4574 0.2286 0.021 Uiso 1 1 calc R . . C2S C 0.4259(3) 0.4468(4) 0.3805(2) 0.0447(11) Uani 1 1 d . . . H2SA H 0.4162 0.5056 0.4169 0.054 Uiso 1 1 calc R . . H2SB H 0.4487 0.3837 0.4113 0.054 Uiso 1 1 calc R . . H2SC H 0.3603 0.4317 0.3482 0.054 Uiso 1 1 calc R . . C3S C 0.6051(3) 0.5041(3) 0.3659(2) 0.0380(10) Uani 1 1 d . . . H3SA H 0.6260 0.4542 0.4091 0.046 Uiso 1 1 calc R . . H3SB H 0.6030 0.5760 0.3875 0.046 Uiso 1 1 calc R . . H3SC H 0.6552 0.5013 0.3264 0.046 Uiso 1 1 calc R . . C11S C 0.1408(3) 0.4039(3) 0.2486(2) 0.0293(8) Uani 1 1 d . A . H11S H 0.0790 0.4434 0.2509 0.035 Uiso 1 1 calc R . . C12S C 0.068(3) 0.232(2) 0.2583(19) 0.039(2) Uani 0.24(3) 1 d P A 1 H12A H 0.0871 0.1984 0.3100 0.058 Uiso 0.24(3) 1 calc PR A 1 H12B H 0.0660 0.1789 0.2160 0.058 Uiso 0.24(3) 1 calc PR A 1 H12C H -0.0005 0.2650 0.2579 0.058 Uiso 0.24(3) 1 calc PR A 1 C13S C 0.256(3) 0.252(4) 0.248(3) 0.066(4) Uani 0.24(3) 1 d P A 1 H13A H 0.2863 0.2758 0.2005 0.099 Uiso 0.24(3) 1 calc PR A 1 H13B H 0.2543 0.1743 0.2492 0.099 Uiso 0.24(3) 1 calc PR A 1 H13C H 0.2985 0.2778 0.2959 0.099 Uiso 0.24(3) 1 calc PR A 1 C21S C 0.8206(3) 0.5531(3) 0.22489(19) 0.0253(7) Uani 1 1 d . . . H21S H 0.7591 0.5270 0.1960 0.030 Uiso 1 1 calc R . . C22S C 0.9140(3) 0.7026(3) 0.2838(2) 0.0413(10) Uani 1 1 d . . . H22A H 0.9666 0.6485 0.2985 0.050 Uiso 1 1 calc R . . H22B H 0.8975 0.7399 0.3317 0.050 Uiso 1 1 calc R . . H22C H 0.9405 0.7534 0.2469 0.050 Uiso 1 1 calc R . . C23S C 0.7332(3) 0.7203(3) 0.2270(2) 0.0415(10) Uani 1 1 d . . . H23A H 0.6744 0.6776 0.2040 0.050 Uiso 1 1 calc R . . H23B H 0.7493 0.7743 0.1885 0.050 Uiso 1 1 calc R . . H23C H 0.7154 0.7548 0.2757 0.050 Uiso 1 1 calc R . . N1S N 0.5039(2) 0.4756(2) 0.32839(15) 0.0233(6) Uani 1 1 d . . . N11S N 0.1324(3) 0.3008(2) 0.24684(18) 0.0357(8) Uani 1 1 d . . . N21S N 0.8219(2) 0.6529(2) 0.24565(16) 0.0252(6) Uani 1 1 d . . . O1S O 0.54703(16) 0.49844(16) 0.20430(12) 0.0167(4) Uani 1 1 d . . . O11S O 0.2210(2) 0.4542(2) 0.24745(15) 0.0413(7) Uani 1 1 d . . . O21S O 0.8923(2) 0.4903(2) 0.23956(15) 0.0387(7) Uani 1 1 d . . . C13T C 0.2150(11) 0.2336(11) 0.2440(8) 0.066(4) Uani 0.76(3) 1 d P A 2 H13D H 0.2747 0.2737 0.2295 0.099 Uiso 0.76(3) 1 calc PR A 2 H13E H 0.1969 0.1783 0.2042 0.099 Uiso 0.76(3) 1 calc PR A 2 H13F H 0.2322 0.2008 0.2964 0.099 Uiso 0.76(3) 1 calc PR A 2 C12T C 0.0297(10) 0.2532(7) 0.2557(5) 0.039(2) Uani 0.76(3) 1 d P A 2 H12D H 0.0318 0.2182 0.3076 0.058 Uiso 0.76(3) 1 calc PR A 2 H12E H 0.0127 0.2012 0.2132 0.058 Uiso 0.76(3) 1 calc PR A 2 H12F H -0.0230 0.3090 0.2520 0.058 Uiso 0.76(3) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu3 0.00958(17) 0.01054(18) 0.01352(17) -0.00123(14) -0.00003(13) 0.00040(13) I1 0.02173(12) 0.01480(11) 0.04220(14) 0.00192(10) 0.00460(9) -0.00133(8) I2 0.01607(12) 0.03635(16) 0.05728(17) -0.00967(12) 0.00247(10) 0.00632(10) O1 0.0120(10) 0.0216(11) 0.0185(11) -0.0016(9) 0.0023(9) 0.0025(9) O2 0.0168(11) 0.0130(11) 0.0166(11) -0.0016(8) -0.0026(8) -0.0029(8) O11 0.0217(11) 0.0151(11) 0.0160(11) 0.0002(9) 0.0010(9) -0.0028(9) O12 0.0114(10) 0.0213(12) 0.0194(11) -0.0028(9) 0.0028(9) 0.0024(9) C1 0.0090(14) 0.0113(15) 0.0227(16) 0.0021(12) -0.0006(12) -0.0016(11) C2 0.0202(16) 0.0222(17) 0.0179(16) 0.0027(13) -0.0012(13) 0.0003(13) C3 0.0202(16) 0.0179(17) 0.0249(17) -0.0035(13) -0.0014(13) -0.0012(13) C4 0.0122(15) 0.0129(16) 0.0349(19) 0.0018(13) -0.0045(13) -0.0006(12) C5 0.0168(15) 0.0224(18) 0.0218(16) 0.0046(14) 0.0035(13) -0.0009(13) C6 0.0164(15) 0.0218(17) 0.0221(16) 0.0006(14) 0.0015(13) 0.0018(13) C7 0.0083(14) 0.0148(16) 0.0235(16) 0.0025(13) 0.0011(12) 0.0032(11) C11 0.0143(15) 0.0109(15) 0.0215(16) -0.0039(12) 0.0009(12) -0.0017(12) C12 0.0221(17) 0.0263(19) 0.0282(18) -0.0006(15) 0.0055(14) -0.0016(14) C13 0.0235(18) 0.034(2) 0.0312(19) -0.0021(16) 0.0098(15) 0.0022(15) C14 0.0110(16) 0.0247(19) 0.042(2) -0.0067(15) 0.0031(14) 0.0015(13) C15 0.0218(18) 0.029(2) 0.0327(19) -0.0070(15) -0.0055(15) 0.0013(15) C16 0.0199(17) 0.0268(19) 0.0248(17) -0.0052(15) 0.0038(14) 0.0011(14) C17 0.0090(13) 0.0083(14) 0.0220(16) -0.0022(12) -0.0001(12) 0.0008(11) C1S 0.0149(16) 0.0163(16) 0.0200(16) 0.0000(12) -0.0018(13) -0.0013(12) C2S 0.030(2) 0.078(3) 0.028(2) 0.012(2) 0.0106(16) -0.003(2) C3S 0.029(2) 0.061(3) 0.0211(18) 0.0068(17) -0.0075(15) -0.0162(18) C11S 0.0253(19) 0.034(2) 0.0296(19) 0.0048(16) 0.0055(15) -0.0004(16) C12S 0.049(6) 0.027(4) 0.044(3) 0.003(3) 0.023(4) -0.006(4) C13S 0.064(8) 0.071(6) 0.063(4) -0.004(4) 0.005(6) 0.050(7) C21S 0.0194(17) 0.033(2) 0.0237(17) -0.0068(15) 0.0013(13) -0.0050(15) C22S 0.037(2) 0.035(2) 0.047(2) -0.0004(19) -0.0142(19) -0.0116(18) C23S 0.037(2) 0.038(2) 0.046(2) -0.0108(19) -0.0093(18) 0.0100(18) N1S 0.0159(14) 0.0381(18) 0.0161(13) 0.0032(12) 0.0032(11) -0.0012(12) N11S 0.051(2) 0.0298(18) 0.0277(16) 0.0043(13) 0.0115(15) 0.0067(15) N21S 0.0209(15) 0.0283(16) 0.0244(14) -0.0007(12) -0.0065(11) 0.0002(12) O1S 0.0149(11) 0.0209(11) 0.0140(10) -0.0005(9) 0.0007(8) 0.0012(9) O11S 0.0308(15) 0.0542(18) 0.0392(15) 0.0055(14) 0.0048(12) -0.0133(13) O21S 0.0357(16) 0.0391(16) 0.0394(15) -0.0081(12) -0.0047(12) 0.0099(13) C13T 0.064(8) 0.071(6) 0.063(4) -0.004(4) 0.005(6) 0.050(7) C12T 0.049(6) 0.027(4) 0.044(3) 0.003(3) 0.023(4) -0.006(4) _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 Cu3 Cu3 2.6052(9) 3_665 ? Cu3 O1 1.958(2) . ? Cu3 O2 1.949(2) 3_665 ? Cu3 O11 1.953(2) . ? Cu3 O12 1.959(2) 3_665 ? Cu3 O1S 2.137(2) . ? I1 C4 2.078(3) . ? I2 C14 2.087(3) . ? O1 C17 1.260(3) . ? O2 Cu3 1.950(2) 3_665 ? O2 C7 1.265(4) . ? O11 C7 1.246(4) . ? O12 Cu3 1.959(2) 3_665 ? O12 C17 1.255(3) . ? C1 C2 1.376(4) . ? C1 C6 1.391(4) . ? C1 C7 1.489(4) . ? C2 C3 1.387(4) . ? C3 C4 1.386(4) . ? C4 C5 1.393(5) . ? C5 C6 1.374(4) . ? C11 C12 1.397(4) . ? C11 C16 1.390(4) . ? C11 C17 1.492(4) . ? C12 C13 1.386(5) . ? C13 C14 1.366(5) . ? C14 C15 1.400(5) . ? C15 C16 1.383(5) . ? C1S N1S 1.314(4) . ? C1S O1S 1.234(3) . ? C2S N1S 1.458(4) . ? C3S N1S 1.442(4) . ? C11S N11S 1.306(5) . ? C11S O11S 1.223(4) . ? C12S N11S 1.23(3) . ? C13S N11S 1.72(4) . ? C21S N21S 1.306(4) . ? C21S O21S 1.228(4) . ? C22S N21S 1.441(4) . ? C23S N21S 1.441(4) . ? N11S C13T 1.373(12) . ? N11S C12T 1.485(11) . ? 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 Cu3 Cu3 86.36(7) . 3_665 ? O1 Cu3 O12 169.19(8) . 3_665 ? O1 Cu3 O1S 97.44(9) . . ? O2 Cu3 Cu3 84.03(6) 3_665 3_665 ? O2 Cu3 O1 87.94(9) 3_665 . ? O2 Cu3 O11 169.26(8) 3_665 . ? O2 Cu3 O12 90.78(9) 3_665 3_665 ? O2 Cu3 O1S 96.11(8) 3_665 . ? O11 Cu3 Cu3 85.37(6) . 3_665 ? O11 Cu3 O1 89.74(9) . . ? O11 Cu3 O12 89.53(9) . 3_665 ? O11 Cu3 O1S 94.59(8) . . ? O12 Cu3 Cu3 82.83(7) 3_665 3_665 ? O12 Cu3 O1S 93.37(8) 3_665 . ? O1S Cu3 Cu3 176.20(6) . 3_665 ? C17 O1 Cu3 120.53(19) . . ? C7 O2 Cu3 122.54(19) . 3_665 ? C7 O11 Cu3 121.17(19) . . ? C17 O12 Cu3 124.68(18) . 3_665 ? C2 C1 C6 119.6(3) . . ? C2 C1 C7 120.5(3) . . ? C6 C1 C7 119.9(3) . . ? C1 C2 C3 120.6(3) . . ? C4 C3 C2 118.9(3) . . ? C3 C4 I1 119.6(2) . . ? C3 C4 C5 121.3(3) . . ? C5 C4 I1 119.1(2) . . ? C6 C5 C4 118.6(3) . . ? C5 C6 C1 121.0(3) . . ? O2 C7 C1 115.6(3) . . ? O11 C7 O2 126.8(3) . . ? O11 C7 C1 117.6(3) . . ? C12 C11 C17 121.1(3) . . ? C16 C11 C12 118.4(3) . . ? C16 C11 C17 120.5(3) . . ? C13 C12 C11 121.0(3) . . ? C14 C13 C12 119.6(3) . . ? C13 C14 I2 121.0(3) . . ? C13 C14 C15 120.9(3) . . ? C15 C14 I2 118.1(2) . . ? C16 C15 C14 118.9(3) . . ? C15 C16 C11 121.2(3) . . ? O1 C17 C11 117.0(3) . . ? O12 C17 O1 125.6(3) . . ? O12 C17 C11 117.4(2) . . ? O1S C1S N1S 123.5(3) . . ? O11S C11S N11S 125.9(4) . . ? O21S C21S N21S 125.5(3) . . ? C1S N1S C2S 121.4(3) . . ? C1S N1S C3S 121.3(3) . . ? C3S N1S C2S 117.3(3) . . ? C11S N11S C13S 106.3(18) . . ? C11S N11S C13T 123.5(8) . . ? C11S N11S C12T 118.4(5) . . ? C12S N11S C11S 138.8(16) . . ? C12S N11S C13S 113(2) . . ? C12S N11S C13T 96.8(14) . . ? C12S N11S C12T 21.3(14) . . ? C13T N11S C13S 17(2) . . ? C13T N11S C12T 117.9(6) . . ? C12T N11S C13S 134.6(17) . . ? C21S N21S C22S 121.7(3) . . ? C21S N21S C23S 121.6(3) . . ? C23S N21S C22S 116.6(3) . . ? C1S O1S Cu3 123.93(19) . . ? data_ilb1169_0m _database_code_depnum_ccdc_archive 'CCDC 912208' #TrackingRef '5_dabco.cif' _audit_creation_date 2013-01-09 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C36 H32 Cu2 I4 N2 O8' _chemical_formula_sum 'C36 H32 Cu2 I4 N2 O8' _chemical_formula_weight 1255.32 _chemical_melting_point ? 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _space_group_crystal_system tetragonal _space_group_IT_number 87 _space_group_name_H-M_alt 'I 4/m' _space_group_name_Hall '-I 4' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-y, x, z' 3 '-x, -y, z' 4 'y, -x, z' 5 'x+1/2, y+1/2, z+1/2' 6 '-y+1/2, x+1/2, z+1/2' 7 '-x+1/2, -y+1/2, z+1/2' 8 'y+1/2, -x+1/2, z+1/2' 9 '-x, -y, -z' 10 'y, -x, -z' 11 'x, y, -z' 12 '-y, x, -z' 13 '-x+1/2, -y+1/2, -z+1/2' 14 'y+1/2, -x+1/2, -z+1/2' 15 'x+1/2, y+1/2, -z+1/2' 16 '-y+1/2, x+1/2, -z+1/2' _cell_length_a 13.4825(4) _cell_length_b 13.4825(4) _cell_length_c 9.8363(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1788.02(9) _cell_formula_units_Z 2 _cell_measurement_reflns_used 975 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 20.60 _cell_measurement_theta_min 2.56 _exptl_absorpt_coefficient_mu 4.699 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6408 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0548 before and 0.0404 after correction. The Ratio of minimum to maximum transmission is 0.8594. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour 'clear light green' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 2.332 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1192 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.015 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0745 _diffrn_reflns_av_unetI/netI 0.0462 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 7097 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 2.14 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _reflns_number_gt 751 _reflns_number_total 1094 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _refine_diff_density_max 3.068 _refine_diff_density_min -2.523 _refine_diff_density_rms 0.318 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 65 _refine_ls_number_reflns 1094 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1200 _refine_ls_R_factor_gt 0.0858 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1435P)^2^+76.2587P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2484 _refine_ls_wR_factor_ref 0.2747 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H2 of C2, H3 of C3, {H12A,H12B} of C12, {H11A,H11B} of C11 2. Uiso/Uaniso restraints and constraints : with sigma of 0.1 and sigma for terminal atoms of 0.2 Uiso(C11) = Uiso(C12) 3. Others Fixed Sof: C12(0.5) H12A(0.5) H12B(0.5) C11(0.5) H11A(0.5) H11B(0.5) 4.a Riding coordinates: C12(H12A,H12B), C11(H11A,H11B) 4.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.0000 0.0000 -0.1383(2) 0.0219(6) Uani 1 4 d S . . O1 O -0.1291(7) 0.0656(7) -0.1120(9) 0.035(2) Uani 1 1 d . . . C2 C -0.3233(11) 0.1264(10) -0.1202(16) 0.042(3) Uani 1 1 d . . . H2 H -0.2884 0.1232 -0.2040 0.050 Uiso 1 1 calc R . . C7 C -0.1676(13) 0.0792(12) 0.0000 0.029(3) Uani 1 2 d S . . C1 C -0.2734(13) 0.1146(12) 0.0000 0.031(4) Uani 1 2 d S . . I1 I -0.63258(11) 0.15882(13) 0.0000 0.0580(7) Uani 1 2 d S . . C3 C -0.4259(11) 0.1431(12) -0.1196(17) 0.050(4) Uani 1 1 d . . . H3 H -0.4604 0.1511 -0.2031 0.060 Uiso 1 1 calc R . . C4 C -0.4762(18) 0.1479(17) 0.0000 0.053(6) Uani 1 2 d S . . N11 N 0.0000 0.0000 -0.3644(19) 0.026(4) Uani 1 4 d S . . C12 C 0.061(3) -0.085(3) -0.424(4) 0.066(7) Uiso 0.50 1 d P . 2 H12A H 0.1302 -0.0785 -0.3907 0.079 Uiso 0.50 1 d PR . 2 H12B H 0.0350 -0.1495 -0.3907 0.079 Uiso 0.50 1 d PR . 2 C11 C 0.102(3) -0.012(3) -0.413(4) 0.066(7) Uiso 0.50 1 d P . 1 H11A H 0.1418 0.0445 -0.3794 0.079 Uiso 0.50 1 d PR . 1 H11B H 0.1316 -0.0749 -0.3794 0.079 Uiso 0.50 1 d PR . 1 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 0.0287(9) 0.0287(9) 0.0082(11) 0.000 0.000 0.000 O1 0.038(5) 0.045(5) 0.023(4) 0.006(4) -0.001(4) 0.013(4) C2 0.043(8) 0.046(8) 0.036(8) -0.004(6) -0.002(6) 0.010(6) C7 0.040(9) 0.021(8) 0.027(8) 0.000 0.000 0.001(7) C1 0.032(9) 0.024(8) 0.037(10) 0.000 0.000 -0.002(6) I1 0.0448(9) 0.0669(11) 0.0622(12) 0.000 0.000 -0.0018(7) C3 0.044(8) 0.053(9) 0.053(9) 0.010(7) -0.004(7) 0.007(6) C4 0.052(13) 0.043(12) 0.065(15) 0.000 0.000 0.012(9) N11 0.031(6) 0.031(6) 0.018(9) 0.000 0.000 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 Cu1 2.721(5) 9 ? Cu1 O1 1.970(8) 4 ? Cu1 O1 1.970(8) . ? Cu1 O1 1.970(8) 3 ? Cu1 O1 1.970(8) 2 ? Cu1 N11 2.224(18) . ? O1 C7 1.231(12) . ? C2 C1 1.370(17) . ? C2 C3 1.40(2) . ? C7 O1 1.231(12) 11 ? C7 C1 1.51(2) . ? C1 C2 1.370(17) 11 ? I1 C4 2.11(2) . ? C3 C4 1.36(2) . ? C4 C3 1.36(2) 11 ? N11 C12 1.53(4) 2 ? N11 C12 1.53(4) 3 ? N11 C12 1.53(4) 4 ? N11 C12 1.53(4) . ? N11 C11 1.47(4) . ? N11 C11 1.47(4) 2 ? N11 C11 1.47(4) 4 ? N11 C11 1.47(4) 3 ? C12 C12 1.50(8) 11_554 ? C12 C12 2.00(6) 2 ? C12 C12 2.00(6) 4 ? C11 C11 1.70(8) 11_554 ? C11 C11 1.97(5) 2 ? C11 C11 1.97(5) 4 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 Cu1 82.4(3) 2 9 ? O1 Cu1 Cu1 82.4(3) 3 9 ? O1 Cu1 Cu1 82.4(3) 4 9 ? O1 Cu1 Cu1 82.4(3) . 9 ? O1 Cu1 O1 89.01(7) . 4 ? O1 Cu1 O1 89.01(7) 2 3 ? O1 Cu1 O1 89.01(7) 4 3 ? O1 Cu1 O1 164.9(5) . 3 ? O1 Cu1 O1 164.9(5) 4 2 ? O1 Cu1 O1 89.01(7) . 2 ? O1 Cu1 N11 97.6(3) 3 . ? O1 Cu1 N11 97.6(3) 4 . ? O1 Cu1 N11 97.6(3) . . ? O1 Cu1 N11 97.6(3) 2 . ? N11 Cu1 Cu1 180.000(1) . 9 ? C7 O1 Cu1 123.8(9) . . ? C1 C2 C3 120.0(14) . . ? O1 C7 O1 126.9(17) . 11 ? O1 C7 C1 116.5(8) . . ? O1 C7 C1 116.5(8) 11 . ? C2 C1 C2 119.4(17) . 11 ? C2 C1 C7 120.2(9) 11 . ? C2 C1 C7 120.2(9) . . ? C4 C3 C2 120.3(16) . . ? C3 C4 I1 120.1(11) 11 . ? C3 C4 I1 120.1(11) . . ? C3 C4 C3 120(2) . 11 ? C12 N11 Cu1 112.4(16) 3 . ? C12 N11 Cu1 112.4(16) 2 . ? C12 N11 Cu1 112.4(16) . . ? C12 N11 Cu1 112.4(16) 4 . ? C12 N11 C12 81.7(11) . 2 ? C12 N11 C12 135(3) 4 2 ? C12 N11 C12 81.7(11) . 4 ? C12 N11 C12 135(3) . 3 ? C12 N11 C12 81.7(11) 2 3 ? C12 N11 C12 81.7(11) 4 3 ? C11 N11 Cu1 109.1(17) . . ? C11 N11 Cu1 109.1(17) 4 . ? C11 N11 Cu1 109.1(17) 3 . ? C11 N11 Cu1 109.1(17) 2 . ? C11 N11 C12 44.4(19) 2 2 ? C11 N11 C12 39.7(19) 3 4 ? C11 N11 C12 39.7(19) 4 . ? C11 N11 C12 118(2) 3 . ? C11 N11 C12 118(2) 2 4 ? C11 N11 C12 121(2) . 4 ? C11 N11 C12 118(2) 4 2 ? C11 N11 C12 121(2) 3 2 ? C11 N11 C12 44.4(19) 3 3 ? C11 N11 C12 39.7(19) 2 3 ? C11 N11 C12 121(2) 4 3 ? C11 N11 C12 118(2) . 3 ? C11 N11 C12 121(2) 2 . ? C11 N11 C12 44.4(19) . . ? C11 N11 C12 44.4(19) 4 4 ? C11 N11 C12 39.7(19) . 2 ? C11 N11 C11 83.8(11) 2 . ? C11 N11 C11 142(3) 3 . ? C11 N11 C11 83.8(11) 4 . ? C11 N11 C11 83.8(11) 3 2 ? C11 N11 C11 142(3) 4 2 ? C11 N11 C11 83.8(11) 4 3 ? N11 C12 C12 49.2(6) . 4 ? N11 C12 C12 49.2(6) . 2 ? C12 C12 N11 112.4(16) 11_554 . ? C12 C12 C12 89.999(6) 11_554 4 ? C12 C12 C12 90.001(4) 11_554 2 ? C12 C12 C12 90.001(4) 2 4 ? N11 C11 C11 109.1(17) . 11_554 ? N11 C11 C11 48.1(5) . 2 ? N11 C11 C11 48.1(5) . 4 ? C11 C11 C11 90.000(1) 11_554 2 ? C11 C11 C11 89.997(6) 11_554 4 ? C11 C11 C11 89.998(6) 2 4 ? data_ilb1173_0m _database_code_depnum_ccdc_archive 'CCDC 912209' #TrackingRef '6_bipy.cif' _audit_creation_date 2013-01-07 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C38 H24 Cu2 I4 N2 O8' _chemical_formula_sum 'C38 H24 Cu2 I4 N2 O8' _chemical_formula_weight 1271.27 _chemical_melting_point ? 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 1 21/c 1' _space_group_name_Hall '-P 2ybc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _cell_length_a 15.230(3) _cell_length_b 22.664(5) _cell_length_c 27.692(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.821(10) _cell_angle_gamma 90.00 _cell_volume 9320(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1558 _cell_measurement_temperature 150.15 _cell_measurement_theta_max 16.848 _cell_measurement_theta_min 2.435 _exptl_absorpt_coefficient_mu 3.608 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.056012 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0885 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.056012. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour 'clear light green' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.812 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 4800 _exptl_crystal_size_max 0.02 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.1888 _diffrn_reflns_av_unetI/netI 0.3486 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 25328 _diffrn_reflns_theta_full 21.05 _diffrn_reflns_theta_max 21.05 _diffrn_reflns_theta_min 0.75 _diffrn_ambient_temperature 150.15 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _reflns_number_gt 2769 _reflns_number_total 10006 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction 'SAINT v6.45A (Bruker, 2003)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 3.891 _refine_diff_density_min -1.861 _refine_diff_density_rms 0.310 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.906 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 337 _refine_ls_number_reflns 10006 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.3100 _refine_ls_R_factor_gt 0.1425 _refine_ls_restrained_S_all 0.906 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3537 _refine_ls_wR_factor_ref 0.4112 _refine_special_details ; Theta(max) is low due to the very small and weakly diffracting crystal. 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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H82 of C82, H2 of C2, H16 of C16, H88 of C88, H93 of C93, H95 of C95, H9C of C9C, H99 of C99, H22 of C22, H92 of C92, H89 of C89, H73 of C73, H86 of C86, H66 of C66, H72 of C72, H3 of C3, H25 of C25, H65 of C65, H56 of C56, H6 of C6, H12 of C12, H96 of C96, H13 of C13, H46 of C46, H45 of C45, H23 of C23, H32 of C32, H8C of C8C, H98 of C98, H33 of C33, H55 of C55, H76 of C76, H63 of C63, H5 of C5, H75 of C75, H52 of C52, H62 of C62, H85 of C85, H36 of C36, H42 of C42, H8B of C8B, H9B of C9B, H53 of C53, H15 of C15, H35 of C35, H43 of C43, H83 of C83, H26 of C26 2. Restrained distances C64-I64A ~ C64-I64B with sigma of 0.0001 3. Rigid bond restraints C11, C12, C13, C14, C15, C16 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 C82, C83, C84, C85, C86 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 C61, C62, C64, C65, C66, C63 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 C54, C55, C56, C51, C52, C53 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 4. Uiso/Uaniso restraints and constraints C13 ~ C12 ~ C14 ~ C15 ~ C16 ~ C11: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 C86 ~ C85 ~ N81 ~ C82 ~ C83 ~ C84: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 C66 ~ C61 ~ C62 ~ C63 ~ C64 ~ C65: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 C53 ~ C52 ~ C51 ~ C56 ~ C55 ~ C54: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08 Uanis(I4B) = Uanis(I4A) Uanis(I64A) = Uanis(I64B) 5. Others Sof(I4A)=1-Sof(I4B) Sof(I64A)=1-Sof(I64B) 6.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C22(H22), C23(H23), C25(H25), C26(H26), C32(H32), C33(H33), C36(H36), C35(H35), C42(H42), C43(H43), C45(H45), C46(H46), C52(H52), C53(H53), C55(H55), C56(H56), C62(H62), C63(H63), C65(H65), C66(H66), C72(H72), C73(H73), C75(H75), C76(H76), C82(H82), C83(H83), C85(H85), C86(H86), C92(H92), C93(H93), C95(H95), C96(H96), C88(H88), C89(H89), C8B(H8B), C8C(H8C), C98(H98), C99(H99), C9B(H9B), C9C(H9C) 6.b Fitted hexagon refined as free rotating group: C1(C2,C3,C4,C5,C6), C11(C12,C13,C14,C15,C16), C21(C22,C23,C24,C25,C26), C31(C32,C33,C34,C36,C35), C41(C42,C43,C44,C45,C46), C51(C52,C53,C54,C55,C56), C61(C62,C63,C64,C65,C66), C71(C72,C73,C74,C75,C76), N81(C82,C83,C84,C85,C86), N91(C92,C93,C94,C95,C96), N87(C88,C89,C8A,C8B,C8C), N97(C98,C99,C9A,C9B,C9C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 -0.3292(3) 0.2891(2) 0.12480(18) 0.0477(15) Uiso 1 1 d . . . Cu4 Cu 0.0827(3) 0.25214(18) 0.38990(16) 0.0338(12) Uiso 1 1 d . . . Cu3 Cu 0.1068(3) 0.27029(19) 0.48592(16) 0.0383(13) Uiso 1 1 d . . . Cu2 Cu -0.3040(3) 0.2644(2) 0.22029(17) 0.0436(14) Uiso 1 1 d . . . I34 I 0.4295(2) 0.57909(14) 0.41376(14) 0.0890(13) Uani 1 1 d . . . I24 I -0.2175(2) -0.06300(15) 0.46870(16) 0.1099(15) Uani 1 1 d . . . I44 I -0.6441(3) 0.59002(16) 0.21561(17) 0.1162(16) Uani 1 1 d . . . I14 I 0.5967(3) 0.04813(19) 0.48937(16) 0.1252(16) Uani 1 1 d . . . I74 I 0.0002(3) -0.03854(18) 0.12476(16) 0.1224(17) Uani 1 1 d . . . I54 I -0.8069(3) 0.0552(2) 0.10782(18) 0.1388(18) Uani 1 1 d . . . I64A I 0.1996(13) 0.4711(10) 0.2244(8) 0.114(3) Uani 0.276(13) 1 d PD A 1 I64B I 0.2281(4) 0.4315(5) 0.2220(3) 0.114(3) Uani 0.724(13) 1 d PD A 2 I4A I -0.4122(11) 0.4559(7) 0.3920(5) 0.092(4) Uani 0.534(13) 1 d P B 1 I4B I -0.4458(13) 0.4252(7) 0.3934(6) 0.092(4) Uani 0.466(13) 1 d P B 2 O22 O 0.0474(15) 0.1962(10) 0.4819(9) 0.043(7) Uiso 1 1 d . . . O12 O 0.2131(15) 0.2311(10) 0.4925(9) 0.047(7) Uiso 1 1 d . . . O32 O 0.1545(15) 0.3240(9) 0.3919(9) 0.040(7) Uiso 1 1 d . . . O21 O 0.0079(17) 0.1829(11) 0.3981(10) 0.060(8) Uiso 1 1 d . . . O52 O -0.2666(18) 0.2122(12) 0.1276(11) 0.076(9) Uiso 1 1 d . . . O2 O -0.0088(14) 0.3118(9) 0.4670(8) 0.037(6) Uiso 1 1 d . B . O1 O -0.0264(15) 0.3019(10) 0.3842(9) 0.043(7) Uiso 1 1 d . B . O62 O -0.1961(16) 0.3126(10) 0.2265(9) 0.052(7) Uiso 1 1 d . A . O51 O -0.2353(16) 0.1930(10) 0.2115(9) 0.052(7) Uiso 1 1 d . . . O41 O -0.3931(16) 0.3574(10) 0.1387(9) 0.052(7) Uiso 1 1 d . . . O61 O -0.2185(18) 0.3284(11) 0.1435(10) 0.068(9) Uiso 1 1 d . A . O72 O -0.4510(17) 0.2452(11) 0.1153(10) 0.060(8) Uiso 1 1 d . . . O31 O 0.1698(16) 0.3448(10) 0.4727(9) 0.054(8) Uiso 1 1 d . . . O42 O -0.3765(15) 0.3373(9) 0.2221(9) 0.040(7) Uiso 1 1 d . . . O11 O 0.1920(16) 0.2072(10) 0.4122(9) 0.052(7) Uiso 1 1 d . . . O71 O -0.4170(17) 0.2220(12) 0.1947(11) 0.075(9) Uiso 1 1 d . . . C1 C -0.1387(11) 0.3512(9) 0.4126(8) 0.024(9) Uiso 1 1 d G B . C2 C -0.1757(15) 0.3618(9) 0.4534(6) 0.035(10) Uiso 1 1 d G . . H2 H -0.1426 0.3524 0.4857 0.043 Uiso 1 1 calc R . . C3 C -0.2613(16) 0.3863(10) 0.4468(8) 0.076(14) Uiso 1 1 d G B . H3 H -0.2866 0.3936 0.4747 0.091 Uiso 1 1 calc R . . C4 C -0.3098(12) 0.4001(10) 0.3995(10) 0.056(12) Uiso 1 1 d G . . C5 C -0.2728(15) 0.3894(10) 0.3587(7) 0.066(13) Uiso 1 1 d G B . H5 H -0.3060 0.3988 0.3264 0.079 Uiso 1 1 calc R . . C6 C -0.1873(16) 0.3650(10) 0.3653(7) 0.039(10) Uiso 1 1 d G . . H6 H -0.1620 0.3577 0.3374 0.047 Uiso 1 1 calc R B . C7 C -0.047(2) 0.3182(16) 0.4181(15) 0.045(11) Uiso 1 1 d . . . C11 C 0.3243(12) 0.1684(10) 0.4666(10) 0.045(10) Uiso 1 1 d GU . . C12 C 0.3425(17) 0.1370(12) 0.4268(7) 0.083(14) Uiso 1 1 d GU . . H12 H 0.3008 0.1376 0.3958 0.100 Uiso 1 1 calc R . . C13 C 0.4218(19) 0.1048(11) 0.4325(8) 0.125(17) Uiso 1 1 d GU . . H13 H 0.4343 0.0834 0.4053 0.151 Uiso 1 1 calc R . . C14 C 0.4829(14) 0.1040(10) 0.4780(10) 0.041(10) Uiso 1 1 d GU . . C15 C 0.4647(13) 0.1354(10) 0.5178(7) 0.050(11) Uiso 1 1 d GU . . H15 H 0.5065 0.1348 0.5489 0.060 Uiso 1 1 calc R . . C16 C 0.3854(15) 0.1676(9) 0.5121(8) 0.030(9) Uiso 1 1 d GU . . H16 H 0.3729 0.1890 0.5393 0.036 Uiso 1 1 calc R . . C17 C 0.244(3) 0.1999(17) 0.4596(15) 0.057(12) Uiso 1 1 d . . . C21 C -0.0421(15) 0.1100(9) 0.4510(10) 0.035(10) Uiso 1 1 d G . . C22 C -0.0888(17) 0.0815(11) 0.4086(7) 0.060(12) Uiso 1 1 d G . . H22 H -0.0843 0.0955 0.3769 0.072 Uiso 1 1 calc R . . C23 C -0.1419(15) 0.0327(10) 0.4125(8) 0.074(14) Uiso 1 1 d G . . H23 H -0.1738 0.0133 0.3835 0.089 Uiso 1 1 calc R . . C24 C -0.1485(15) 0.0123(9) 0.4589(10) 0.041(10) Uiso 1 1 d G . . C25 C -0.1019(17) 0.0407(11) 0.5014(7) 0.061(12) Uiso 1 1 d G . . H25 H -0.1064 0.0267 0.5331 0.073 Uiso 1 1 calc R . . C26 C -0.0487(15) 0.0895(10) 0.4974(8) 0.082(15) Uiso 1 1 d G . . H26 H -0.0168 0.1090 0.5265 0.099 Uiso 1 1 calc R . . C27 C 0.010(2) 0.1668(16) 0.4448(14) 0.044(11) Uiso 1 1 d . . . C31 C 0.2399(15) 0.4087(9) 0.4288(9) 0.064(13) Uiso 1 1 d G . . C32 C 0.2827(17) 0.4408(11) 0.4701(7) 0.062(13) Uiso 1 1 d G . . H32 H 0.2752 0.4298 0.5021 0.074 Uiso 1 1 calc R . . C33 C 0.3363(14) 0.4889(10) 0.4647(8) 0.051(12) Uiso 1 1 d G . . H33 H 0.3655 0.5107 0.4930 0.062 Uiso 1 1 calc R . . C34 C 0.3471(15) 0.5049(9) 0.4179(9) 0.045(11) Uiso 1 1 d G . . C36 C 0.3044(16) 0.4729(10) 0.3766(7) 0.094(17) Uiso 1 1 d G . . H36 H 0.3118 0.4839 0.3446 0.113 Uiso 1 1 calc R . . C35 C 0.2507(14) 0.4248(9) 0.3820(7) 0.015(8) Uiso 1 1 d G . . H35 H 0.2215 0.4029 0.3537 0.018 Uiso 1 1 calc R . . C37 C 0.189(2) 0.3529(14) 0.4301(13) 0.031(10) Uiso 1 1 d . . . C41 C -0.4646(15) 0.4205(9) 0.1910(10) 0.056(12) Uiso 1 1 d G . . C42 C -0.5060(16) 0.4544(10) 0.1505(7) 0.054(12) Uiso 1 1 d G . . H42 H -0.4986 0.4445 0.1183 0.064 Uiso 1 1 calc R . . C43 C -0.5582(14) 0.5028(10) 0.1571(7) 0.045(11) Uiso 1 1 d G . . H43 H -0.5865 0.5260 0.1295 0.054 Uiso 1 1 calc R . . C44 C -0.5691(14) 0.5172(9) 0.2042(9) 0.040(10) Uiso 1 1 d G . . C45 C -0.5277(17) 0.4833(11) 0.2447(7) 0.066(13) Uiso 1 1 d G . . H45 H -0.5351 0.4932 0.2769 0.079 Uiso 1 1 calc R . . C46 C -0.4755(16) 0.4349(10) 0.2381(8) 0.077(14) Uiso 1 1 d G . . H46 H -0.4472 0.4118 0.2658 0.092 Uiso 1 1 calc R . . C47 C -0.408(2) 0.3680(15) 0.1820(13) 0.037(10) Uiso 1 1 d . . . C51 C -0.5443(13) 0.1855(10) 0.1407(9) 0.045(10) Uiso 1 1 d GU . . C52 C -0.5619(17) 0.1475(12) 0.1768(7) 0.072(13) Uiso 1 1 d GU . . H52 H -0.5220 0.1460 0.2084 0.086 Uiso 1 1 calc R . . C53 C -0.6377(19) 0.1116(10) 0.1665(10) 0.085(14) Uiso 1 1 d GU . . H53 H -0.6497 0.0856 0.1911 0.102 Uiso 1 1 calc R . . C54 C -0.6960(15) 0.1137(10) 0.1201(11) 0.078(13) Uiso 1 1 d GU . . C55 C -0.6784(15) 0.1518(11) 0.0840(8) 0.069(12) Uiso 1 1 d GU . . H55 H -0.7183 0.1532 0.0524 0.083 Uiso 1 1 calc R . . C56 C -0.6026(16) 0.1877(9) 0.0943(8) 0.034(9) Uiso 1 1 d GU . . H56 H -0.5906 0.2137 0.0697 0.041 Uiso 1 1 calc R . . C57 C -0.223(2) 0.1823(16) 0.1673(15) 0.047(11) Uiso 1 1 d . . . C61 C -0.0785(14) 0.3628(10) 0.1970(11) 0.047(10) Uiso 1 1 d GU A . C62 C -0.0274(18) 0.3717(10) 0.2447(9) 0.056(11) Uiso 1 1 d GU . . H62 H -0.0507 0.3606 0.2724 0.068 Uiso 1 1 calc R . . C63 C 0.0577(17) 0.3968(11) 0.2516(8) 0.057(11) Uiso 1 1 d GU A . H63 H 0.0927 0.4028 0.2842 0.068 Uiso 1 1 calc R . . C64 C 0.0918(14) 0.4130(10) 0.2110(12) 0.091(14) Uiso 1 1 d GDU . . C65 C 0.041(2) 0.4041(12) 0.1633(9) 0.081(14) Uiso 1 1 d GU A . H65 H 0.0640 0.4152 0.1355 0.097 Uiso 1 1 calc R . . C66 C -0.0445(19) 0.3790(12) 0.1563(8) 0.111(16) Uiso 1 1 d GU . . H66 H -0.0794 0.3730 0.1238 0.134 Uiso 1 1 calc R A . C67 C -0.169(3) 0.3364(17) 0.1879(16) 0.060(13) Uiso 1 1 d . . . C71 C -0.1776(16) 0.1286(10) 0.1577(10) 0.074(14) Uiso 1 1 d G . . C72 C -0.1322(18) 0.0950(12) 0.1975(8) 0.070(14) Uiso 1 1 d G . . H72 H -0.1359 0.1052 0.2303 0.084 Uiso 1 1 calc R . . C73 C -0.0813(16) 0.0466(11) 0.1893(9) 0.071(14) Uiso 1 1 d G . . H73 H -0.0503 0.0237 0.2164 0.085 Uiso 1 1 calc R . . C74 C -0.0759(17) 0.0318(10) 0.1413(11) 0.100(17) Uiso 1 1 d G . . C75 C -0.1214(18) 0.0654(12) 0.1015(8) 0.070(14) Uiso 1 1 d G . . H75 H -0.1177 0.0553 0.0688 0.084 Uiso 1 1 calc R . . C76 C -0.1722(15) 0.1138(11) 0.1097(9) 0.049(11) Uiso 1 1 d G . . H76 H -0.2032 0.1368 0.0826 0.059 Uiso 1 1 calc R . . C77 C -0.459(3) 0.2218(18) 0.1450(17) 0.059(13) Uiso 1 1 d . . . N81 N 0.1084(15) 0.2756(10) 0.5642(6) 0.049(9) Uiso 1 1 d GU . . C82 C 0.0463(14) 0.3102(9) 0.5813(8) 0.060(12) Uiso 1 1 d GU . . H82 H 0.0078 0.3361 0.5592 0.072 Uiso 1 1 calc R . . C83 C 0.0406(13) 0.3070(9) 0.6306(8) 0.042(10) Uiso 1 1 d GU . . H83 H -0.0019 0.3306 0.6423 0.050 Uiso 1 1 calc R . . C84 C 0.0970(15) 0.2691(10) 0.6629(6) 0.031(9) Uiso 1 1 d GU . . C85 C 0.1591(14) 0.2345(9) 0.6458(8) 0.044(10) Uiso 1 1 d GU . . H85 H 0.1976 0.2086 0.6678 0.053 Uiso 1 1 calc R . . C86 C 0.1648(14) 0.2378(9) 0.5965(9) 0.076(13) Uiso 1 1 d GU . . H86 H 0.2073 0.2141 0.5848 0.091 Uiso 1 1 calc R . . N91 N -0.3001(14) 0.2468(9) 0.2960(6) 0.042(8) Uiso 1 1 d G . . C92 C -0.3797(12) 0.2601(9) 0.3103(7) 0.043(10) Uiso 1 1 d G . . H92 H -0.4301 0.2746 0.2866 0.052 Uiso 1 1 calc R . . C93 C -0.3856(12) 0.2524(9) 0.3593(8) 0.042(11) Uiso 1 1 d G . . H93 H -0.4400 0.2615 0.3690 0.051 Uiso 1 1 calc R . . C94 C -0.3119(15) 0.2312(10) 0.3939(6) 0.042(10) Uiso 1 1 d G . . C95 C -0.2323(12) 0.2179(9) 0.3796(7) 0.033(10) Uiso 1 1 d G . . H95 H -0.1819 0.2035 0.4033 0.039 Uiso 1 1 calc R . . C96 C -0.2264(11) 0.2257(9) 0.3306(8) 0.043(11) Uiso 1 1 d G . . H96 H -0.1720 0.2166 0.3208 0.052 Uiso 1 1 calc R . . N87 N 0.0790(15) 0.2595(9) 0.8126(6) 0.042(8) Uiso 1 1 d G . . C88 C 0.1611(12) 0.2491(10) 0.8000(7) 0.075(14) Uiso 1 1 d G . . H88 H 0.2129 0.2401 0.8251 0.090 Uiso 1 1 calc R . . C89 C 0.1674(11) 0.2517(10) 0.7507(8) 0.059(12) Uiso 1 1 d G . . H89 H 0.2235 0.2446 0.7422 0.071 Uiso 1 1 calc R . . C8A C 0.0916(14) 0.2648(9) 0.7141(6) 0.013(8) Uiso 1 1 d G . . C8B C 0.0095(12) 0.2753(9) 0.7266(7) 0.035(10) Uiso 1 1 d G . . H8B H -0.0422 0.2842 0.7016 0.042 Uiso 1 1 calc R . . C8C C 0.0033(11) 0.2726(9) 0.7759(8) 0.030(9) Uiso 1 1 d G . . H8C H -0.0528 0.2797 0.7845 0.036 Uiso 1 1 calc R . . N97 N -0.3347(18) 0.2117(12) 0.5437(7) 0.081(12) Uiso 1 1 d G . . C98 C -0.3831(15) 0.2543(10) 0.5127(10) 0.074(14) Uiso 1 1 d G . . H98 H -0.4231 0.2798 0.5247 0.088 Uiso 1 1 calc R . . C99 C -0.3731(15) 0.2597(9) 0.4642(9) 0.060(12) Uiso 1 1 d G . . H99 H -0.4062 0.2888 0.4431 0.072 Uiso 1 1 calc R . . C9A C -0.3146(16) 0.2224(11) 0.4468(7) 0.031(9) Uiso 1 1 d G . . C9B C -0.2661(15) 0.1798(10) 0.4778(10) 0.065(13) Uiso 1 1 d G . . H9B H -0.2261 0.1544 0.4658 0.078 Uiso 1 1 calc R . . C9C C -0.2762(16) 0.1745(10) 0.5263(9) 0.073(14) Uiso 1 1 d G . . H9C H -0.2431 0.1454 0.5475 0.087 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 I34 0.086(3) 0.057(2) 0.116(3) 0.013(2) 0.006(2) -0.014(2) I24 0.084(3) 0.081(3) 0.157(4) 0.055(3) 0.009(3) -0.011(2) I44 0.112(3) 0.068(3) 0.148(4) -0.002(3) -0.015(3) 0.019(2) I14 0.110(3) 0.121(3) 0.126(4) 0.006(3) -0.015(3) 0.019(3) I74 0.129(4) 0.117(3) 0.112(3) -0.038(3) 0.008(3) 0.020(3) I54 0.126(4) 0.134(4) 0.138(4) 0.002(3) -0.008(3) -0.018(3) I64A 0.141(5) 0.129(8) 0.063(3) -0.004(5) 0.000(3) -0.069(5) I64B 0.141(5) 0.129(8) 0.063(3) -0.004(5) 0.000(3) -0.069(5) I4A 0.119(10) 0.103(10) 0.041(2) -0.011(7) -0.011(5) 0.040(7) I4B 0.119(10) 0.103(10) 0.041(2) -0.011(7) -0.011(5) 0.040(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 Cu2 2.646(7) . ? Cu1 O52 1.98(3) . ? Cu1 O41 1.91(2) . ? Cu1 O61 1.87(3) . ? Cu1 O72 2.07(3) . ? Cu1 N97 2.228(18) 4_565 ? Cu4 Cu3 2.634(6) . ? Cu4 O32 1.96(2) . ? Cu4 O21 1.98(3) . ? Cu4 O1 1.99(2) . ? Cu4 O11 1.93(2) . ? Cu4 N87 2.146(15) 4_565 ? Cu3 O22 1.90(2) . ? Cu3 O12 1.82(2) . ? Cu3 O2 1.96(2) . ? Cu3 O31 2.01(2) . ? Cu3 N81 2.166(16) . ? Cu2 O62 1.95(2) . ? Cu2 O51 1.97(2) . ? Cu2 O42 1.99(2) . ? Cu2 O71 1.96(3) . ? Cu2 N91 2.121(15) . ? I34 C34 2.115(16) . ? I24 C24 2.054(17) . ? I44 C44 2.070(17) . ? I14 C14 2.113(18) . ? I74 C74 2.081(19) . ? I54 C54 2.115(18) . ? I64A C64 2.073(19) . ? I64B C64 2.073(19) . ? I4A C4 1.98(2) . ? I4B C4 2.12(2) . ? O22 C27 1.25(4) . ? O12 C17 1.32(4) . ? O32 C37 1.26(3) . ? O21 C27 1.34(4) . ? O52 C57 1.34(4) . ? O2 C7 1.36(4) . ? O1 C7 1.11(4) . ? O62 C67 1.35(4) . ? O51 C57 1.30(4) . ? O41 C47 1.29(4) . ? O61 C67 1.31(4) . ? O72 C77 1.00(4) . ? O31 C37 1.29(4) . ? O42 C47 1.31(4) . ? O11 C17 1.38(4) . ? O71 C77 1.38(4) . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C1 C7 1.56(4) . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C4 C5 1.3900 . ? C5 C6 1.3900 . ? C11 C12 1.3900 . ? C11 C16 1.3900 . ? C11 C17 1.39(4) . ? C12 C13 1.3900 . ? C13 C14 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C21 C27 1.54(4) . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? C31 C32 1.3900 . ? C31 C35 1.3900 . ? C31 C37 1.49(3) . ? C32 C33 1.3900 . ? C33 C34 1.3900 . ? C34 C36 1.3900 . ? C36 C35 1.3900 . ? C41 C42 1.3900 . ? C41 C46 1.3900 . ? C41 C47 1.52(4) . ? C42 C43 1.3900 . ? C43 C44 1.3900 . ? C44 C45 1.3900 . ? C45 C46 1.3900 . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C51 C77 1.53(4) . ? C52 C53 1.3900 . ? C53 C54 1.3900 . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? C57 C71 1.45(4) . ? C61 C62 1.3900 . ? C61 C66 1.3900 . ? C61 C67 1.47(4) . ? C62 C63 1.3900 . ? C63 C64 1.3900 . ? C64 C65 1.3900 . ? C65 C66 1.3900 . ? C71 C72 1.3900 . ? C71 C76 1.3900 . ? C72 C73 1.3900 . ? C73 C74 1.3900 . ? C74 C75 1.3900 . ? C75 C76 1.3900 . ? N81 C82 1.3900 . ? N81 C86 1.3900 . ? C82 C83 1.3900 . ? C83 C84 1.3900 . ? C84 C85 1.3900 . ? C84 C8A 1.44(2) . ? C85 C86 1.3900 . ? N91 C92 1.3900 . ? N91 C96 1.3900 . ? C92 C93 1.3900 . ? C93 C94 1.3900 . ? C94 C95 1.3900 . ? C94 C9A 1.49(2) . ? C95 C96 1.3900 . ? N87 Cu4 2.145(15) 4_566 ? N87 C88 1.3900 . ? N87 C8C 1.3900 . ? C88 C89 1.3900 . ? C89 C8A 1.3900 . ? C8A C8B 1.3900 . ? C8B C8C 1.3900 . ? N97 Cu1 2.228(18) 4_566 ? N97 C98 1.3900 . ? N97 C9C 1.3900 . ? C98 C99 1.3900 . ? C99 C9A 1.3900 . ? C9A C9B 1.3900 . ? C9B C9C 1.3900 . ? 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 O52 Cu1 Cu2 79.2(8) . . ? O52 Cu1 O72 89.5(11) . . ? O52 Cu1 N97 86.6(11) . 4_565 ? O41 Cu1 Cu2 86.4(8) . . ? O41 Cu1 O52 165.1(11) . . ? O41 Cu1 O72 86.2(10) . . ? O41 Cu1 N97 107.7(10) . 4_565 ? O61 Cu1 Cu2 84.4(9) . . ? O61 Cu1 O52 90.7(11) . . ? O61 Cu1 O41 91.5(11) . . ? O61 Cu1 O72 171.5(12) . . ? O61 Cu1 N97 96.5(11) . 4_565 ? O72 Cu1 Cu2 87.3(8) . . ? O72 Cu1 N97 92.0(11) . 4_565 ? N97 Cu1 Cu2 165.9(7) 4_565 . ? O32 Cu4 Cu3 83.6(7) . . ? O32 Cu4 O21 171.3(10) . . ? O32 Cu4 O1 89.0(9) . . ? O32 Cu4 N87 91.2(9) . 4_565 ? O21 Cu4 Cu3 87.9(8) . . ? O21 Cu4 O1 88.1(10) . . ? O21 Cu4 N87 97.4(10) . 4_565 ? O1 Cu4 Cu3 85.3(7) . . ? O1 Cu4 N87 98.9(9) . 4_565 ? O11 Cu4 Cu3 81.0(8) . . ? O11 Cu4 O32 89.6(9) . . ? O11 Cu4 O21 91.3(10) . . ? O11 Cu4 O1 166.3(10) . . ? O11 Cu4 N87 94.8(9) . 4_565 ? N87 Cu4 Cu3 173.3(6) 4_565 . ? O22 Cu3 Cu4 81.1(7) . . ? O22 Cu3 O2 91.2(9) . . ? O22 Cu3 O31 166.0(10) . . ? O22 Cu3 N81 90.4(9) . . ? O12 Cu3 Cu4 87.0(8) . . ? O12 Cu3 O22 88.6(10) . . ? O12 Cu3 O2 170.5(10) . . ? O12 Cu3 O31 88.8(10) . . ? O12 Cu3 N81 96.6(10) . . ? O2 Cu3 Cu4 83.6(7) . . ? O2 Cu3 O31 89.1(9) . . ? O2 Cu3 N81 92.9(9) . . ? O31 Cu3 Cu4 85.0(7) . . ? O31 Cu3 N81 103.5(9) . . ? N81 Cu3 Cu4 170.7(6) . . ? O62 Cu2 Cu1 84.4(7) . . ? O62 Cu2 O51 90.6(10) . . ? O62 Cu2 O42 89.7(10) . . ? O62 Cu2 O71 164.1(11) . . ? O62 Cu2 N91 100.4(9) . . ? O51 Cu2 Cu1 90.7(7) . . ? O51 Cu2 O42 174.4(10) . . ? O51 Cu2 N91 93.9(9) . . ? O42 Cu2 Cu1 83.8(7) . . ? O42 Cu2 N91 91.5(9) . . ? O71 Cu2 Cu1 79.7(8) . . ? O71 Cu2 O51 90.0(11) . . ? O71 Cu2 O42 88.2(10) . . ? O71 Cu2 N91 95.4(10) . . ? N91 Cu2 Cu1 173.3(6) . . ? C27 O22 Cu3 130(2) . . ? C17 O12 Cu3 130(3) . . ? C37 O32 Cu4 126(2) . . ? C27 O21 Cu4 116(2) . . ? C57 O52 Cu1 129(2) . . ? C7 O2 Cu3 119(2) . . ? C7 O1 Cu4 120(3) . . ? C67 O62 Cu2 124(3) . . ? C57 O51 Cu2 117(2) . . ? C47 O41 Cu1 123(2) . . ? C67 O61 Cu1 129(3) . . ? C77 O72 Cu1 114(3) . . ? C37 O31 Cu3 120(2) . . ? C47 O42 Cu2 121(2) . . ? C17 O11 Cu4 130(2) . . ? C77 O71 Cu2 122(3) . . ? C2 C1 C6 120.0 . . ? C2 C1 C7 121(2) . . ? C6 C1 C7 118(2) . . ? C1 C2 C3 120.0 . . ? C2 C3 C4 120.0 . . ? I4A C4 I4B 24.2(4) . . ? C3 C4 I4A 118.9(15) . . ? C3 C4 I4B 116.2(15) . . ? C3 C4 C5 120.0 . . ? C5 C4 I4A 118.5(15) . . ? C5 C4 I4B 123.2(15) . . ? C6 C5 C4 120.0 . . ? C5 C6 C1 120.0 . . ? O2 C7 C1 109(3) . . ? O1 C7 O2 132(4) . . ? O1 C7 C1 119(4) . . ? C12 C11 C16 120.0 . . ? C12 C11 C17 118(3) . . ? C16 C11 C17 122(3) . . ? C11 C12 C13 120.0 . . ? C12 C13 C14 120.0 . . ? C13 C14 I14 120.3(15) . . ? C15 C14 I14 119.3(15) . . ? C15 C14 C13 120.0 . . ? C16 C15 C14 120.0 . . ? C15 C16 C11 120.0 . . ? O12 C17 O11 112(3) . . ? O12 C17 C11 128(4) . . ? O11 C17 C11 120(3) . . ? C22 C21 C26 120.0 . . ? C22 C21 C27 118(2) . . ? C26 C21 C27 122(2) . . ? C21 C22 C23 120.0 . . ? C24 C23 C22 120.0 . . ? C23 C24 I24 122.9(15) . . ? C23 C24 C25 120.0 . . ? C25 C24 I24 117.0(15) . . ? C26 C25 C24 120.0 . . ? C25 C26 C21 120.0 . . ? O22 C27 O21 124(3) . . ? O22 C27 C21 120(3) . . ? O21 C27 C21 116(3) . . ? C32 C31 C35 120.0 . . ? C32 C31 C37 125(2) . . ? C35 C31 C37 115(2) . . ? C31 C32 C33 120.0 . . ? C34 C33 C32 120.0 . . ? C33 C34 I34 117.0(14) . . ? C33 C34 C36 120.0 . . ? C36 C34 I34 123.0(14) . . ? C35 C36 C34 120.0 . . ? C36 C35 C31 120.0 . . ? O32 C37 O31 124(3) . . ? O32 C37 C31 123(3) . . ? O31 C37 C31 112(3) . . ? C42 C41 C46 120.0 . . ? C42 C41 C47 118(2) . . ? C46 C41 C47 122(2) . . ? C41 C42 C43 120.0 . . ? C44 C43 C42 120.0 . . ? C43 C44 I44 121.0(14) . . ? C43 C44 C45 120.0 . . ? C45 C44 I44 119.0(14) . . ? C46 C45 C44 120.0 . . ? C45 C46 C41 120.0 . . ? O41 C47 O42 125(3) . . ? O41 C47 C41 122(3) . . ? O42 C47 C41 113(3) . . ? C52 C51 C56 120.0 . . ? C52 C51 C77 125(3) . . ? C56 C51 C77 114(3) . . ? C53 C52 C51 120.0 . . ? C54 C53 C52 120.0 . . ? C53 C54 I54 116.8(16) . . ? C53 C54 C55 120.0 . . ? C55 C54 I54 123.2(16) . . ? C56 C55 C54 120.0 . . ? C55 C56 C51 120.0 . . ? O52 C57 C71 116(3) . . ? O51 C57 O52 122(3) . . ? O51 C57 C71 120(3) . . ? C62 C61 C66 120.0 . . ? C62 C61 C67 122(3) . . ? C66 C61 C67 118(3) . . ? C61 C62 C63 120.0 . . ? C64 C63 C62 120.0 . . ? I64B C64 I64A 28.0(7) . . ? C63 C64 I64A 116.5(18) . . ? C63 C64 I64B 118.4(17) . . ? C63 C64 C65 120.0 . . ? C65 C64 I64A 121.1(18) . . ? C65 C64 I64B 120.0(17) . . ? C66 C65 C64 120.0 . . ? C65 C66 C61 120.0 . . ? O62 C67 C61 118(4) . . ? O61 C67 O62 118(4) . . ? O61 C67 C61 123(4) . . ? C72 C71 C57 119(3) . . ? C72 C71 C76 120.0 . . ? C76 C71 C57 121(3) . . ? C71 C72 C73 120.0 . . ? C74 C73 C72 120.0 . . ? C73 C74 I74 123.3(17) . . ? C73 C74 C75 120.0 . . ? C75 C74 I74 116.7(17) . . ? C76 C75 C74 120.0 . . ? C75 C76 C71 120.0 . . ? O72 C77 O71 135(5) . . ? O72 C77 C51 118(4) . . ? O71 C77 C51 106(3) . . ? C82 N81 Cu3 121.0(13) . . ? C82 N81 C86 120.0 . . ? C86 N81 Cu3 118.5(13) . . ? N81 C82 C83 120.0 . . ? C84 C83 C82 120.0 . . ? C83 C84 C8A 120.7(18) . . ? C85 C84 C83 120.0 . . ? C85 C84 C8A 119.3(18) . . ? C84 C85 C86 120.0 . . ? C85 C86 N81 120.0 . . ? C92 N91 Cu2 114.0(12) . . ? C92 N91 C96 120.0 . . ? C96 N91 Cu2 126.0(12) . . ? N91 C92 C93 120.0 . . ? C94 C93 C92 120.0 . . ? C93 C94 C95 120.0 . . ? C93 C94 C9A 122.1(18) . . ? C95 C94 C9A 117.9(18) . . ? C96 C95 C94 120.0 . . ? C95 C96 N91 120.0 . . ? C88 N87 Cu4 113.8(12) . 4_566 ? C88 N87 C8C 120.0 . . ? C8C N87 Cu4 126.1(12) . 4_566 ? N87 C88 C89 120.0 . . ? C88 C89 C8A 120.0 . . ? C89 C8A C84 120.9(17) . . ? C8B C8A C84 119.1(17) . . ? C8B C8A C89 120.0 . . ? C8A C8B C8C 120.0 . . ? C8B C8C N87 120.0 . . ? C98 N97 Cu1 121.6(15) . 4_566 ? C98 N97 C9C 120.0 . . ? C9C N97 Cu1 117.5(15) . 4_566 ? N97 C98 C99 120.0 . . ? C9A C99 C98 120.0 . . ? C99 C9A C94 115(2) . . ? C99 C9A C9B 120.0 . . ? C9B C9A C94 125(2) . . ? C9C C9B C9A 120.0 . . ? C9B C9C N97 120.0 . . ? _smtbx_masks_special_details ? loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 0.000 0.000 0.000 62.6 0.0 ? 2 0.285 0.149 0.308 426.1 89.1 ? 3 -0.285 -0.149 0.692 426.1 87.4 ? 4 -0.104 0.235 0.557 27.3 0.0 ? 5 -0.104 0.265 0.057 27.3 0.0 ? 6 0.285 0.351 0.808 426.1 88.5 ? 7 0.000 0.500 0.500 62.6 0.0 ? 8 -0.285 0.649 0.192 426.1 88.0 ? 9 0.104 0.735 0.943 27.3 0.0 ? 10 0.104 0.765 0.443 27.3 0.0 ? data_twin4_a _database_code_depnum_ccdc_archive 'CCDC 912210' #TrackingRef '7_bpe_twin.cif' _audit_creation_date 2013-01-07 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C52 H40 Cu2 I4 N4 O8, 2(C7 H8 O)' _chemical_formula_sum 'C66 H56 Cu2 I4 N4 O10' _chemical_formula_weight 1699.83 _chemical_melting_point ? 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _cell_length_a 8.2079(19) _cell_length_b 16.029(4) _cell_length_c 24.699(6) _cell_angle_alpha 102.764(17) _cell_angle_beta 98.004(16) _cell_angle_gamma 101.353(14) _cell_volume 3049.9(12) _cell_formula_units_Z 2 _cell_measurement_reflns_used 323 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 21.96 _cell_measurement_theta_min 2.68 _exptl_absorpt_coefficient_mu 2.785 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.421601 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2008/4 (Bruker,2010) was used for absorption correction. For component 1: wR2(int) was 0.1410 before and 0.0953 after correction. The Ratio of minimum to maximum transmission not present. The \l/2 correction factor is Not present For component 2: wR2(int) was 0.1419 before and 0.0989 after correction. The Ratio of minimum to maximum transmission is 0.57. The \l/2 correction factor is Not present ; _exptl_crystal_colour 'clear dark violet' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.851 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1660 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.1972 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 15917 _diffrn_reflns_theta_full 24.69 _diffrn_reflns_theta_max 24.69 _diffrn_reflns_theta_min 0.86 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.954 _diffrn_measured_fraction_theta_max 0.954 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 6714 _reflns_number_total 15920 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SAINT v6.45A (Bruker, 2003)' _computing_data_collection ? _computing_data_reduction 'SAINT v7.68A (Bruker, 2009)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; XL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution ; XS, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _refine_diff_density_max 2.479 _refine_diff_density_min -2.177 _refine_diff_density_rms 0.294 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 433 _refine_ls_number_reflns 15920 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2310 _refine_ls_R_factor_gt 0.1080 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1512P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2654 _refine_ls_wR_factor_ref 0.3417 _refine_special_details ; The crystal was a 2 component twin. Refinements were carried out against hklf 5 data. Please ignore the resulting checkcif alerts. For reflection statistics for each components see supplementary information table S3. 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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H62 of C62, H32 of C32, {H59a,H59b} of C59, H11 of C11, H35 of C35, H39 of C39, H25 of C25, H12 of C12, H40 of C40, H53 of C53, H42 of C42, H61 of C61, H3 of C3, H64 of C64, H60 of C60, H4 of C4, H14 of C14, H18 of C18, H52 of C52, {H6a,H6b} of C6, H21 of C21, H13 of C13, H20 of C20, H26 of C26, H5 of C5, H28 of C28, H36 of C36, H54 of C54, H49 of C49, H65 of C65, {H57a,H57b} of C57, H9 of C9, H16 of C16, H43 of C43, H47 of C47, H27 of C27, H46 of C46, H1 of C1, H10 of C10, H17 of C17, H55 of C55, H50 of C50, {H58a,H58b} of C58, H19 of C19, {H66a,H66b} of C66, H56 of C56, H33 of C33, {H7a,H7b} of C7 At 1.5 times of: H10a of O10, H9a of O9 2.a Secondary CH2 refined with riding coordinates: C7(H7a,H7b), C6(H6a,H6b), C57(H57a,H57b), C58(H58a,H58b), C66(H66a,H66b), C59(H59a,H59b) 2.b Aromatic/amide H refined with riding coordinates: C36(H36), C18(H18), C33(H33), C17(H17), C1(H1), C56(H56), C49(H49), C43(H43), C26(H26), C40(H40), C4(H4), C9(H9), C25(H25), C16(H16), C50(H50), C12(H12), C13(H13), C53(H53), C21(H21), C46(H46), C20(H20), C47(H47), C52(H52), C28(H28), C14(H14), C11(H11), C32(H32), C3(H3), C27(H27), C42(H42), C39(H39), C35(H35), C5(H5), C10(H10), C54(H54), C55(H55), C19(H19), C62(H62), C64(H64), C65(H65), C60(H60), C61(H61) 2.c Idealised tetrahedral OH refined as rotating group: O9(H9a), O10(H10a) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 I1 I 0.6815(2) 0.42379(11) 0.39453(6) 0.0404(5) Uani 1 1 d . . . I2 I -0.0993(2) -0.08944(11) 1.10195(6) 0.0428(5) Uani 1 1 d . . . I3 I -0.8266(2) -0.04530(11) 0.39785(6) 0.0382(4) Uani 1 1 d . . . I4 I 1.3961(2) 0.44251(12) 1.10863(6) 0.0472(5) Uani 1 1 d . . . Cu5 Cu -0.4739(3) -0.07341(19) 0.74967(12) 0.0225(5) Uani 1 1 d . . . Cu6 Cu 1.0335(3) 0.42129(18) 0.75018(12) 0.0217(5) Uani 1 1 d . . . C41 C 0.766(3) 0.4302(14) 0.4805(8) 0.025(5) Uiso 1 1 d . . . C48 C -0.738(3) -0.0601(14) 0.4792(8) 0.026(5) Uiso 1 1 d . . . O3 O 1.0071(15) 0.3930(8) 0.6672(5) 0.029(3) Uani 1 1 d . . . O4 O 0.8995(15) 0.5082(7) 0.6913(5) 0.027(3) Uani 1 1 d . . . C34 C 1.320(3) 0.4331(14) 1.0243(8) 0.024(5) Uiso 1 1 d . . . O2 O 1.0676(15) 0.4574(9) 0.8337(5) 0.034(3) Uani 1 1 d . . . O5 O -0.4212(16) 0.0151(8) 0.8523(5) 0.036(3) Uani 1 1 d . . . N1 N -0.2473(18) -0.0022(11) 0.7450(7) 0.024(3) Uiso 1 1 d . . . O9 O 0.5899(17) 0.1908(8) 0.8613(6) 0.053(4) Uani 1 1 d . . . H9A H 0.5945 0.1393 0.8626 0.079 Uiso 1 1 calc R . . O7 O -0.4889(15) -0.1517(8) 0.6481(5) 0.035(3) Uani 1 1 d . . . O1 O 1.1779(18) 0.3421(8) 0.8121(5) 0.044(4) Uani 1 1 d . . . C29 C -0.176(3) -0.0764(15) 1.0216(8) 0.033(6) Uiso 1 1 d . . . N2 N 0.8052(19) 0.3438(12) 0.7445(8) 0.032(4) Uani 1 1 d . . . N3 N -1.7428(19) -0.4954(12) 0.7534(8) 0.030(3) Uiso 1 1 d . . . O6 O -0.5825(16) -0.0351(10) 0.6857(6) 0.040(4) Uani 1 1 d . . . N4 N -0.6972(18) -0.1419(11) 0.7569(7) 0.021(3) Uiso 1 1 d . . . O8 O -0.3620(16) -0.1092(9) 0.8152(5) 0.036(4) Uani 1 1 d . . . C36 C 1.292(2) 0.3551(13) 0.9264(8) 0.027(5) Uiso 1 1 d . . . H36 H 1.3168 0.3094 0.8994 0.033 Uiso 1 1 calc R . . C23 C -0.364(3) -0.0493(14) 0.8552(8) 0.032(5) Uiso 1 1 d . . . C18 C -1.629(2) -0.5213(12) 0.7248(7) 0.021(4) Uiso 1 1 d . . . H18 H -1.6488 -0.5814 0.7049 0.025 Uiso 1 1 calc R . . C33 C 1.234(3) 0.4922(16) 1.0035(9) 0.042(6) Uiso 1 1 d . . . H33 H 1.2179 0.5410 1.0302 0.050 Uiso 1 1 calc R . . C17 C -0.771(2) -0.2203(11) 0.7179(7) 0.022(4) Uiso 1 1 d . . . H17 H -0.7238 -0.2366 0.6853 0.026 Uiso 1 1 calc R . . C1 C -0.132(2) -0.0430(12) 0.7262(7) 0.022(4) Uiso 1 1 d . . . H1 H -0.1652 -0.1050 0.7110 0.027 Uiso 1 1 calc R . . C56 C 0.895(3) 0.2991(13) 0.9959(8) 0.035(5) Uiso 1 1 d . . . H56 H 0.9870 0.3295 0.9829 0.042 Uiso 1 1 calc R . . C30 C 1.145(3) 0.4060(15) 0.8468(9) 0.040(6) Uiso 1 1 d . . . C49 C -0.758(3) 0.0014(17) 0.5247(9) 0.045(6) Uiso 1 1 d . . . H49 H -0.8040 0.0499 0.5203 0.053 Uiso 1 1 calc R . . C24 C -0.298(2) -0.0592(12) 0.9137(7) 0.022(4) Uiso 1 1 d . . . C43 C 0.800(3) 0.5059(14) 0.5763(9) 0.038(6) Uiso 1 1 d . . . H43 H 0.7786 0.5514 0.6044 0.045 Uiso 1 1 calc R . . C26 C -0.171(3) -0.1380(14) 0.9745(8) 0.029(5) Uiso 1 1 d . . . H26 H -0.1329 -0.1889 0.9786 0.034 Uiso 1 1 calc R . . C40 C 0.847(3) 0.3706(14) 0.4938(8) 0.031(5) Uiso 1 1 d . . . H40 H 0.8684 0.3258 0.4652 0.038 Uiso 1 1 calc R . . C45 C -0.621(2) -0.0772(12) 0.5855(8) 0.027(5) Uiso 1 1 d . . . C4 C -0.043(2) 0.1322(13) 0.7675(7) 0.029(5) Uiso 1 1 d . . . H4 H -0.0204 0.1945 0.7795 0.035 Uiso 1 1 calc R . . C44 C -0.563(3) -0.0919(14) 0.6413(8) 0.038(5) Uiso 1 1 d . . . C9 C 0.538(2) 0.3202(12) 0.7712(8) 0.038(5) Uiso 1 1 d . . . H9 H 0.4689 0.3401 0.7968 0.046 Uiso 1 1 calc R . . C25 C -0.221(3) -0.1286(14) 0.9205(8) 0.037(6) Uiso 1 1 d . . . H25 H -0.2028 -0.1685 0.8885 0.044 Uiso 1 1 calc R . . C16 C -0.916(2) -0.2770(12) 0.7251(8) 0.034(5) Uiso 1 1 d . . . H16 H -0.9675 -0.3300 0.6968 0.040 Uiso 1 1 calc R . . C37 C 0.932(3) 0.4501(14) 0.6533(9) 0.037(6) Uiso 1 1 d . . . C15 C -0.982(2) -0.2564(13) 0.7720(7) 0.042(5) Uiso 1 1 d . . . C50 C -0.706(3) -0.0118(15) 0.5776(10) 0.050(7) Uiso 1 1 d . . . H50 H -0.7298 0.0251 0.6099 0.060 Uiso 1 1 calc R . . C12 C 0.699(3) 0.3637(14) 0.7782(9) 0.042(6) Uiso 1 1 d . . . H12 H 0.7413 0.4129 0.8100 0.050 Uiso 1 1 calc R . . C38 C 0.880(2) 0.4458(12) 0.5938(7) 0.026(5) Uiso 1 1 d . . . C13 C -0.765(3) -0.1205(14) 0.8005(8) 0.041(6) Uiso 1 1 d . . . H13 H -0.7132 -0.0661 0.8275 0.050 Uiso 1 1 calc R . . C53 C 0.619(3) 0.2169(15) 1.0337(9) 0.056(6) Uiso 1 1 d . . . H53 H 0.5243 0.1898 1.0471 0.067 Uiso 1 1 calc R . . C21 C -1.484(3) -0.4646(13) 0.7229(8) 0.039(5) Uiso 1 1 d . . . H21 H -1.4046 -0.4853 0.7021 0.047 Uiso 1 1 calc R . . C46 C -0.605(3) -0.1374(13) 0.5373(8) 0.032(5) Uiso 1 1 d . . . H46 H -0.5542 -0.1847 0.5412 0.039 Uiso 1 1 calc R . . C20 C -1.570(2) -0.3516(13) 0.7802(8) 0.034(5) Uiso 1 1 d . . . H20 H -1.5567 -0.2913 0.7984 0.041 Uiso 1 1 calc R . . C47 C -0.663(3) -0.1286(13) 0.4834(8) 0.025(5) Uiso 1 1 d . . . H47 H -0.6514 -0.1690 0.4505 0.030 Uiso 1 1 calc R . . C52 C 0.611(3) 0.2123(12) 0.9776(8) 0.034(5) Uiso 1 1 d . . . H52 H 0.5086 0.1812 0.9519 0.041 Uiso 1 1 calc R . . C28 C -0.312(3) 0.0008(14) 0.9617(8) 0.033(5) Uiso 1 1 d . . . H28 H -0.3628 0.0481 0.9582 0.040 Uiso 1 1 calc R . . C14 C -0.906(2) -0.1720(12) 0.8098(8) 0.039(5) Uiso 1 1 d . . . H14 H -0.9545 -0.1516 0.8416 0.047 Uiso 1 1 calc R . . C11 C 0.742(2) 0.2698(12) 0.7026(7) 0.024(4) Uiso 1 1 d . . . H11 H 0.8150 0.2514 0.6782 0.028 Uiso 1 1 calc R . . C32 C 1.176(3) 0.4834(15) 0.9496(9) 0.042(6) Uiso 1 1 d . . . H32 H 1.1149 0.5235 0.9385 0.050 Uiso 1 1 calc R . . C31 C 1.204(2) 0.4133(13) 0.9081(8) 0.031(5) Uiso 1 1 d . . . C8 C 0.471(2) 0.2468(11) 0.7270(6) 0.024(4) Uiso 1 1 d . . . C3 C 0.032(2) -0.0020(12) 0.7271(7) 0.031(5) Uiso 1 1 d . . . H3 H 0.1071 -0.0343 0.7118 0.037 Uiso 1 1 calc R . . C27 C -0.253(3) -0.0085(16) 1.0137(9) 0.043(6) Uiso 1 1 d . . . H27 H -0.2643 0.0332 1.0460 0.052 Uiso 1 1 calc R . . C22 C -1.452(2) -0.3772(13) 0.7513(9) 0.040(5) Uiso 1 1 d . . . C42 C 0.747(3) 0.5032(16) 0.5202(9) 0.036(6) Uiso 1 1 d . . . H42 H 0.7015 0.5482 0.5092 0.044 Uiso 1 1 calc R . . C39 C 0.899(3) 0.3762(14) 0.5508(8) 0.037(6) Uiso 1 1 d . . . H39 H 0.9494 0.3319 0.5610 0.044 Uiso 1 1 calc R . . C35 C 1.343(3) 0.3635(15) 0.9832(8) 0.037(6) Uiso 1 1 d . . . H35 H 1.3958 0.3208 0.9947 0.044 Uiso 1 1 calc R . . C5 C -0.203(2) 0.0815(12) 0.7654(7) 0.026(5) Uiso 1 1 d . . . H5 H -0.2841 0.1105 0.7798 0.031 Uiso 1 1 calc R . . C10 C 0.583(2) 0.2199(12) 0.6926(7) 0.034(5) Uiso 1 1 d . . . H10 H 0.5477 0.1675 0.6628 0.041 Uiso 1 1 calc R . . C2 C 0.086(2) 0.0912(12) 0.7518(8) 0.035(5) Uiso 1 1 d . . . C7 C 0.285(2) 0.1932(12) 0.7161(7) 0.040(5) Uiso 1 1 d . . . H7A H 0.2084 0.2336 0.7200 0.048 Uiso 1 1 calc R . . H7B H 0.2541 0.1544 0.6772 0.048 Uiso 1 1 calc R . . C54 C 0.779(3) 0.2654(14) 1.0732(10) 0.049(6) Uiso 1 1 d . . . H54 H 0.7913 0.2706 1.1127 0.059 Uiso 1 1 calc R . . C55 C 0.906(3) 0.3014(14) 1.0513(9) 0.053(6) Uiso 1 1 d . . . H55 H 1.0103 0.3306 1.0762 0.063 Uiso 1 1 calc R . . C6 C 0.268(2) 0.1378(13) 0.7589(8) 0.048(6) Uiso 1 1 d . . . H6A H 0.3382 0.0942 0.7531 0.058 Uiso 1 1 calc R . . H6B H 0.3080 0.1762 0.7978 0.058 Uiso 1 1 calc R . . C51 C 0.742(3) 0.2499(13) 0.9572(8) 0.039(5) Uiso 1 1 d . . . C19 C -1.712(3) -0.4150(14) 0.7832(9) 0.045(6) Uiso 1 1 d . . . H19 H -1.7868 -0.3983 0.8075 0.053 Uiso 1 1 calc R . . C57 C -1.138(2) -0.3174(12) 0.7822(7) 0.037(5) Uiso 1 1 d . . . H57A H -1.1471 -0.3002 0.8225 0.044 Uiso 1 1 calc R . . H57B H -1.1261 -0.3789 0.7731 0.044 Uiso 1 1 calc R . . C58 C -1.301(3) -0.3112(14) 0.7449(9) 0.054(6) Uiso 1 1 d . . . H58A H -1.3187 -0.2510 0.7562 0.065 Uiso 1 1 calc R . . H58B H -1.2883 -0.3233 0.7048 0.065 Uiso 1 1 calc R . . O10 O 0.2371(18) 0.2436(9) 0.3685(6) 0.058(4) Uani 1 1 d . . . H10A H 0.3336 0.2670 0.3885 0.086 Uiso 1 1 calc R . . C62 C 0.106(3) 0.2019(14) 0.5000(9) 0.040(6) Uiso 1 1 d . . . H62 H -0.0007 0.1619 0.4853 0.049 Uiso 1 1 calc R . . C64 C 0.358(3) 0.2967(14) 0.4879(9) 0.043(6) Uiso 1 1 d . . . H64 H 0.4250 0.3223 0.4648 0.052 Uiso 1 1 calc R . . C65 C 0.409(3) 0.3145(16) 0.5438(10) 0.071(7) Uiso 1 1 d . . . H65 H 0.5183 0.3527 0.5587 0.085 Uiso 1 1 calc R . . C60 C 0.325(3) 0.2847(15) 0.5821(11) 0.061(7) Uiso 1 1 d . . . H60 H 0.3689 0.3039 0.6217 0.073 Uiso 1 1 calc R . . C63 C 0.193(3) 0.2362(13) 0.4640(8) 0.041(5) Uiso 1 1 d . . . C66 C 0.123(3) 0.2104(14) 0.4033(8) 0.048(6) Uiso 1 1 d . . . H66A H 0.0905 0.1453 0.3904 0.058 Uiso 1 1 calc R . . H66B H 0.0181 0.2318 0.3970 0.058 Uiso 1 1 calc R . . C59 C 0.735(3) 0.2501(14) 0.8952(8) 0.052(6) Uiso 1 1 d . . . H59A H 0.7354 0.3101 0.8908 0.062 Uiso 1 1 calc R . . H59B H 0.8369 0.2338 0.8828 0.062 Uiso 1 1 calc R . . C61 C 0.172(3) 0.2242(15) 0.5594(10) 0.063(7) Uiso 1 1 d . . . H61 H 0.1099 0.1974 0.5833 0.075 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 I1 0.0339(9) 0.0467(10) 0.0379(9) 0.0117(7) 0.0029(6) 0.0054(8) I2 0.0515(11) 0.0435(10) 0.0344(8) 0.0105(7) 0.0037(7) 0.0160(8) I3 0.0322(9) 0.0451(10) 0.0396(8) 0.0160(7) 0.0051(6) 0.0097(7) I4 0.0500(11) 0.0539(12) 0.0384(9) 0.0146(7) 0.0032(7) 0.0139(9) Cu5 0.0216(14) 0.0130(13) 0.0309(10) 0.0057(10) 0.0039(12) -0.0003(10) Cu6 0.0226(14) 0.0099(13) 0.0299(10) 0.0043(10) 0.0030(12) -0.0004(10) O3 0.016(7) 0.035(8) 0.031(7) 0.003(6) -0.005(6) 0.002(6) O4 0.022(7) 0.015(7) 0.037(7) -0.001(5) -0.001(6) 0.001(5) O2 0.028(8) 0.037(8) 0.044(8) 0.020(7) 0.007(6) 0.016(7) O5 0.042(9) 0.037(8) 0.037(8) 0.019(6) 0.004(6) 0.019(7) O9 0.058(10) 0.020(7) 0.070(10) -0.002(7) -0.009(8) 0.016(7) O7 0.020(7) 0.031(8) 0.059(9) 0.018(7) 0.007(6) 0.008(6) O1 0.064(11) 0.036(9) 0.030(7) 0.000(6) 0.016(7) 0.012(7) N2 0.023(9) 0.040(11) 0.045(10) 0.030(8) 0.016(8) 0.006(7) O6 0.015(8) 0.065(11) 0.038(8) 0.014(8) 0.002(6) 0.005(7) O8 0.043(9) 0.051(10) 0.026(7) 0.012(7) 0.007(6) 0.032(8) O10 0.060(11) 0.045(9) 0.068(10) 0.012(8) 0.014(8) 0.013(8) _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 I1 C41 2.115(19) . ? I2 C29 2.07(2) . ? I3 C48 2.121(19) . ? I4 C34 2.052(19) . ? Cu5 N1 2.014(13) . ? Cu5 O6 1.979(14) . ? Cu5 N4 1.995(13) . ? Cu5 O8 1.999(13) . ? Cu6 O3 1.970(12) . ? Cu6 O2 1.980(13) . ? Cu6 N2 2.002(13) . ? Cu6 N3 2.027(13) 1_865 ? Cu6 C30 2.52(2) . ? C41 C40 1.34(3) . ? C41 C42 1.40(3) . ? C48 C49 1.37(3) . ? C48 C47 1.37(3) . ? O3 C37 1.28(2) . ? O4 C37 1.27(2) . ? C34 C33 1.43(3) . ? C34 C35 1.40(3) . ? O2 C30 1.21(2) . ? O5 C23 1.22(2) . ? N1 C1 1.33(2) . ? N1 C5 1.28(2) . ? O9 C59 1.40(2) . ? O7 C44 1.26(2) . ? O1 C30 1.28(2) . ? C29 C26 1.36(3) . ? C29 C27 1.40(3) . ? N2 C12 1.32(3) . ? N2 C11 1.35(2) . ? N3 Cu6 2.027(13) 1_245 ? N3 C18 1.32(2) . ? N3 C19 1.29(3) . ? O6 C44 1.31(2) . ? N4 C17 1.37(2) . ? N4 C13 1.29(2) . ? O8 C23 1.22(2) . ? C36 C31 1.40(3) . ? C36 C35 1.37(3) . ? C23 C24 1.52(2) . ? C18 C21 1.36(2) . ? C33 C32 1.32(3) . ? C17 C16 1.40(2) . ? C1 C3 1.37(2) . ? C56 C55 1.35(3) . ? C56 C51 1.43(3) . ? C30 C31 1.49(3) . ? C49 C50 1.39(3) . ? C24 C25 1.41(3) . ? C24 C28 1.39(3) . ? C43 C38 1.38(3) . ? C43 C42 1.38(3) . ? C26 C25 1.39(3) . ? C40 C39 1.39(3) . ? C45 C44 1.48(3) . ? C45 C50 1.40(3) . ? C45 C46 1.39(3) . ? C4 C5 1.39(3) . ? C4 C2 1.40(3) . ? C9 C12 1.34(3) . ? C9 C8 1.37(2) . ? C16 C15 1.35(2) . ? C37 C38 1.45(3) . ? C15 C14 1.43(3) . ? C15 C57 1.54(3) . ? C38 C39 1.41(3) . ? C13 C14 1.37(3) . ? C53 C52 1.36(3) . ? C53 C54 1.48(3) . ? C21 C22 1.38(3) . ? C46 C47 1.40(3) . ? C20 C22 1.35(3) . ? C20 C19 1.41(3) . ? C52 C51 1.34(3) . ? C28 C27 1.36(3) . ? C11 C10 1.35(2) . ? C32 C31 1.42(3) . ? C8 C10 1.40(2) . ? C8 C7 1.55(2) . ? C3 C2 1.44(3) . ? C22 C58 1.52(3) . ? C2 C6 1.50(2) . ? C7 C6 1.53(2) . ? C54 C55 1.33(3) . ? C51 C59 1.53(3) . ? C57 C58 1.54(3) . ? O10 C66 1.46(2) . ? C62 C63 1.35(3) . ? C62 C61 1.43(3) . ? C64 C65 1.34(3) . ? C64 C63 1.46(3) . ? C65 C60 1.36(3) . ? C60 C61 1.39(3) . ? C63 C66 1.47(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O6 Cu5 N1 89.9(7) . . ? O6 Cu5 N4 91.2(7) . . ? O6 Cu5 O8 178.7(6) . . ? N4 Cu5 N1 178.2(7) . . ? N4 Cu5 O8 89.5(7) . . ? O8 Cu5 N1 89.4(7) . . ? O3 Cu6 O2 176.4(5) . . ? O3 Cu6 N2 91.1(7) . . ? O3 Cu6 N3 87.2(6) . 1_865 ? O3 Cu6 C30 153.7(7) . . ? O2 Cu6 N2 91.8(7) . . ? O2 Cu6 N3 89.8(6) . 1_865 ? O2 Cu6 C30 28.0(6) . . ? N2 Cu6 N3 176.3(8) . 1_865 ? N2 Cu6 C30 93.7(8) . . ? N3 Cu6 C30 89.2(8) 1_865 . ? C40 C41 I1 119.4(15) . . ? C40 C41 C42 124(2) . . ? C42 C41 I1 116.4(16) . . ? C49 C48 I3 116.7(17) . . ? C49 C48 C47 124(2) . . ? C47 C48 I3 119.0(14) . . ? C37 O3 Cu6 103.8(12) . . ? C33 C34 I4 123.9(15) . . ? C35 C34 I4 120.5(16) . . ? C35 C34 C33 115.5(19) . . ? C30 O2 Cu6 101.6(13) . . ? C1 N1 Cu5 119.8(13) . . ? C5 N1 Cu5 121.8(13) . . ? C5 N1 C1 118.0(15) . . ? C26 C29 I2 121.8(17) . . ? C26 C29 C27 117(2) . . ? C27 C29 I2 120.7(16) . . ? C12 N2 Cu6 123.6(15) . . ? C12 N2 C11 114.3(15) . . ? C11 N2 Cu6 121.9(13) . . ? C18 N3 Cu6 121.4(13) . 1_245 ? C19 N3 Cu6 119.2(15) . 1_245 ? C19 N3 C18 119.4(16) . . ? C44 O6 Cu5 102.9(13) . . ? C17 N4 Cu5 118.9(11) . . ? C13 N4 Cu5 122.2(14) . . ? C13 N4 C17 118.3(15) . . ? C23 O8 Cu5 102.2(13) . . ? C35 C36 C31 120.5(19) . . ? O5 C23 C24 118.2(17) . . ? O8 C23 O5 125.8(19) . . ? O8 C23 C24 116.0(18) . . ? N3 C18 C21 122.1(18) . . ? C32 C33 C34 124(2) . . ? N4 C17 C16 121.4(16) . . ? N1 C1 C3 124.6(17) . . ? C55 C56 C51 119(2) . . ? O2 C30 Cu6 50.4(11) . . ? O2 C30 O1 125(2) . . ? O2 C30 C31 119(2) . . ? O1 C30 Cu6 75.0(12) . . ? O1 C30 C31 115.8(19) . . ? C31 C30 Cu6 169.1(16) . . ? C48 C49 C50 116(2) . . ? C25 C24 C23 121.6(17) . . ? C28 C24 C23 120.0(17) . . ? C28 C24 C25 118.5(18) . . ? C42 C43 C38 123(2) . . ? C29 C26 C25 122(2) . . ? C41 C40 C39 117.8(19) . . ? C50 C45 C44 124.0(19) . . ? C46 C45 C44 118.0(19) . . ? C46 C45 C50 117.7(19) . . ? C5 C4 C2 120.0(18) . . ? O7 C44 O6 119.6(19) . . ? O7 C44 C45 123.8(19) . . ? O6 C44 C45 116.5(19) . . ? C12 C9 C8 120.0(19) . . ? C26 C25 C24 119.4(19) . . ? C15 C16 C17 120.2(18) . . ? O3 C37 C38 119.5(18) . . ? O4 C37 O3 119.8(19) . . ? O4 C37 C38 120.6(19) . . ? C16 C15 C14 116.3(18) . . ? C16 C15 C57 122.0(17) . . ? C14 C15 C57 121.5(17) . . ? C49 C50 C45 123(2) . . ? N2 C12 C9 125(2) . . ? C43 C38 C37 122.0(18) . . ? C43 C38 C39 116.3(19) . . ? C39 C38 C37 121.5(19) . . ? N4 C13 C14 123.4(19) . . ? C52 C53 C54 118(2) . . ? C18 C21 C22 119.9(19) . . ? C45 C46 C47 120.5(19) . . ? C22 C20 C19 119.7(19) . . ? C48 C47 C46 118.3(18) . . ? C51 C52 C53 123(2) . . ? C27 C28 C24 120(2) . . ? C13 C14 C15 120.1(19) . . ? C10 C11 N2 125.1(17) . . ? C33 C32 C31 120(2) . . ? C36 C31 C30 122.1(18) . . ? C36 C31 C32 118.3(19) . . ? C32 C31 C30 120(2) . . ? C9 C8 C10 116.3(17) . . ? C9 C8 C7 123.0(16) . . ? C10 C8 C7 120.7(15) . . ? C1 C3 C2 118.4(17) . . ? C28 C27 C29 123(2) . . ? C21 C22 C58 120.6(18) . . ? C20 C22 C21 117.4(18) . . ? C20 C22 C58 121.7(19) . . ? C43 C42 C41 116(2) . . ? C40 C39 C38 122(2) . . ? C36 C35 C34 122(2) . . ? N1 C5 C4 123.7(18) . . ? C11 C10 C8 118.6(17) . . ? C4 C2 C3 114.8(16) . . ? C4 C2 C6 124.8(17) . . ? C3 C2 C6 120.4(17) . . ? C6 C7 C8 109.1(15) . . ? C55 C54 C53 117(2) . . ? C54 C55 C56 124(2) . . ? C2 C6 C7 109.5(16) . . ? C56 C51 C59 116.7(18) . . ? C52 C51 C56 119.0(19) . . ? C52 C51 C59 124.2(19) . . ? N3 C19 C20 121(2) . . ? C15 C57 C58 110.4(15) . . ? C22 C58 C57 110.1(16) . . ? C63 C62 C61 122(2) . . ? C65 C64 C63 117(2) . . ? C64 C65 C60 128(3) . . ? C65 C60 C61 115(2) . . ? C62 C63 C64 117.6(19) . . ? C62 C63 C66 120.2(19) . . ? C64 C63 C66 122.2(19) . . ? O10 C66 C63 114.7(17) . . ? O9 C59 C51 110.6(17) . . ? C60 C61 C62 120(2) . . ? #END