# 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_ilb1211_0m _database_code_depnum_ccdc_archive 'CCDC 911300' #TrackingRef '1_pym.cif' _audit_creation_date 2011-06-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H10 Cu I2 N O4, C H4 O' _chemical_formula_sum 'C17 H14 Cu I2 N O5' _chemical_formula_weight 629.63 _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 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.6172(6) _cell_length_b 10.9922(3) _cell_length_c 17.0958(5) _cell_angle_alpha 90.00 _cell_angle_beta 118.3750(10) _cell_angle_gamma 90.00 _cell_volume 3739.59(18) _cell_formula_units_Z 8 _cell_measurement_reflns_used 8358 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 27.576 _cell_measurement_theta_min 2.236 _exptl_absorpt_coefficient_mu 4.498 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.712377 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0733 before and 0.0305 after correction. The Ratio of minimum to maximum transmission is 0.712377. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour translucent _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 2.237 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 2384 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0379 _diffrn_reflns_av_unetI/netI 0.0423 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 29854 _diffrn_reflns_theta_full 30.54 _diffrn_reflns_theta_max 30.54 _diffrn_reflns_theta_min 2.05 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.980 _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 4026 _reflns_number_total 5606 _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 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2007)/Bruker' _refine_diff_density_max 1.994 _refine_diff_density_min -2.294 _refine_diff_density_rms 0.186 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 5606 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0853 _refine_ls_R_factor_gt 0.0561 _refine_ls_restrained_S_all 1.076 _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^)+(0.0578P)^2^+52.8521P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1427 _refine_ls_wR_factor_ref 0.1554 _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. ; _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 I2 I 0.81859(3) 0.12025(8) 0.61296(8) 0.0445(2) Uani 0.942(4) 1 d P A 1 Cu4 Cu 0.50121(3) 0.55018(6) 0.56978(4) 0.01896(15) Uani 1 1 d . . . I1 I 0.62356(7) 0.93098(8) 0.24440(11) 0.0607(4) Uani 0.803(3) 1 d P B 1 O6 O 0.59166(19) 0.4794(4) 0.6337(2) 0.0264(8) Uani 1 1 d . . . O5 O 0.5369(2) 0.6903(4) 0.5332(3) 0.0287(9) Uani 1 1 d . . . N1 N 0.5031(2) 0.6436(4) 0.6827(3) 0.0214(9) Uani 1 1 d . . . O3 O 0.5351(2) 0.6041(4) 0.4137(3) 0.0288(9) Uani 1 1 d . . . C7 C 0.6826(3) 0.3553(6) 0.6544(4) 0.0293(12) Uani 1 1 d . . . C8 C 0.5036(3) 0.7646(5) 0.6841(4) 0.0281(12) Uani 1 1 d . . . H8 H 0.5067 0.8071 0.6377 0.034 Uiso 1 1 calc R . . C9 C 0.5000 0.5881(7) 0.7500 0.0211(15) Uani 1 2 d S . . H9 H 0.5000 0.5016 0.7500 0.025 Uiso 1 2 calc SR . . C10 C 0.5457(3) 0.6922(5) 0.4657(3) 0.0243(11) Uani 1 1 d . . . C11 C 0.5830(4) 0.8145(7) 0.3736(5) 0.0402(16) Uani 1 1 d . B . H11 H 0.5742 0.7459 0.3359 0.048 Uiso 1 1 calc R . . C12 C 0.5800(4) 0.9099(6) 0.5002(4) 0.0369(15) Uani 1 1 d . B . H12 H 0.5686 0.9068 0.5469 0.044 Uiso 1 1 calc R . . C13 C 0.7136(3) 0.3682(6) 0.7465(4) 0.0361(14) Uani 1 1 d . A . H13 H 0.6934 0.4172 0.7731 0.043 Uiso 1 1 calc R . . C14 C 0.5708(3) 0.8082(6) 0.4466(4) 0.0289(12) Uani 1 1 d . . . C16 C 0.7124(3) 0.2808(6) 0.6180(4) 0.0351(14) Uani 1 1 d . A . H16 H 0.6912 0.2691 0.5554 0.042 Uiso 1 1 calc R . . C17 C 0.7729(3) 0.2230(7) 0.6716(4) 0.0369(14) Uani 1 1 d . . . C18 C 0.7740(3) 0.3095(8) 0.7993(4) 0.0449(18) Uani 1 1 d . . . H18 H 0.7949 0.3200 0.8619 0.054 Uiso 1 1 calc R A . C23 C 0.6078(4) 0.9207(7) 0.3567(6) 0.049(2) Uani 1 1 d . . . C24 C 0.5000 0.8303(8) 0.7500 0.0330(19) Uani 1 2 d S . . H24 H 0.5000 0.9167 0.7500 0.040 Uiso 1 2 calc SR . . C25 C 0.8044(4) 0.2366(7) 0.7636(5) 0.0448(17) Uani 1 1 d . A . H25 H 0.8457 0.1968 0.8006 0.054 Uiso 1 1 calc R . . C34 C 0.6212(4) 1.0222(7) 0.4140(6) 0.054(2) Uani 1 1 d . B . H34 H 0.6403 1.0941 0.4046 0.065 Uiso 1 1 calc R . . C37 C 0.6063(4) 1.0159(7) 0.4843(5) 0.054(2) Uani 1 1 d . . . H37 H 0.6142 1.0846 0.5216 0.065 Uiso 1 1 calc R B . C38 C 0.6163(3) 0.4146(5) 0.5962(3) 0.0230(11) Uani 1 1 d . . . O7 O 0.2664(4) 0.3289(9) 0.5125(6) 0.093(3) Uani 1 1 d . . . H7 H 0.2984 0.2965 0.5570 0.140 Uiso 1 1 calc R . . C39 C 0.2911(5) 0.3858(8) 0.4604(6) 0.056(2) Uani 1 1 d . . . H39A H 0.2787 0.3377 0.4066 0.085 Uiso 1 1 calc R . . H39B H 0.3402 0.3921 0.4945 0.085 Uiso 1 1 calc R . . H39C H 0.2717 0.4674 0.4438 0.085 Uiso 1 1 calc R . . O8 O 0.5896(2) 0.3931(4) 0.5139(3) 0.0298(9) Uani 1 1 d . . . I1A I 0.6539(3) 0.9423(4) 0.2890(4) 0.0607(4) Uani 0.197(3) 1 d P B 2 I2A I 0.8188(5) 0.1450(13) 0.5820(12) 0.0445(2) Uani 0.058(4) 1 d P 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 I2 0.0318(3) 0.0501(4) 0.0491(5) 0.0109(3) 0.0171(2) 0.0115(2) Cu4 0.0186(3) 0.0232(3) 0.0153(3) -0.0004(2) 0.0083(2) -0.0023(3) I1 0.0765(8) 0.0538(4) 0.0851(8) 0.0358(5) 0.0656(7) 0.0208(5) O6 0.0209(19) 0.032(2) 0.0218(17) -0.0025(15) 0.0062(14) 0.0012(17) O5 0.034(2) 0.029(2) 0.0273(18) -0.0005(16) 0.0175(17) -0.0059(18) N1 0.020(2) 0.026(2) 0.0188(18) -0.0002(16) 0.0100(16) 0.0003(19) O3 0.038(2) 0.029(2) 0.0278(19) -0.0022(16) 0.0226(18) -0.0102(19) C7 0.019(3) 0.036(3) 0.027(3) 0.000(2) 0.006(2) -0.003(2) C8 0.035(3) 0.024(3) 0.027(2) 0.005(2) 0.016(2) -0.001(2) C9 0.020(4) 0.026(4) 0.015(3) 0.000 0.007(3) 0.000 C10 0.019(3) 0.027(3) 0.025(2) 0.005(2) 0.010(2) -0.003(2) C11 0.042(4) 0.033(4) 0.057(4) 0.013(3) 0.033(3) 0.002(3) C12 0.041(4) 0.026(3) 0.035(3) 0.001(2) 0.011(3) -0.007(3) C13 0.029(3) 0.041(4) 0.031(3) 0.002(3) 0.008(2) 0.001(3) C14 0.026(3) 0.027(3) 0.033(3) 0.004(2) 0.014(2) -0.006(2) C16 0.028(3) 0.039(4) 0.034(3) 0.002(3) 0.011(2) -0.006(3) C17 0.027(3) 0.037(4) 0.042(3) 0.005(3) 0.012(3) -0.002(3) C18 0.029(3) 0.061(5) 0.030(3) 0.009(3) 0.002(3) 0.001(3) C23 0.045(4) 0.041(4) 0.072(5) 0.026(4) 0.037(4) 0.004(3) C24 0.052(6) 0.019(4) 0.034(4) 0.000 0.024(4) 0.000 C25 0.030(3) 0.051(4) 0.041(3) 0.012(3) 0.006(3) 0.002(3) C34 0.043(4) 0.033(4) 0.078(6) 0.018(4) 0.022(4) -0.010(3) C37 0.060(5) 0.034(4) 0.046(4) 0.007(3) 0.008(4) -0.016(4) C38 0.019(3) 0.026(3) 0.021(2) 0.0024(19) 0.0075(19) -0.002(2) O7 0.053(4) 0.093(6) 0.103(6) 0.002(5) 0.012(4) 0.021(4) C39 0.052(5) 0.051(5) 0.067(5) 0.000(4) 0.028(4) -0.002(4) O8 0.022(2) 0.041(3) 0.0221(17) -0.0020(17) 0.0074(15) 0.0056(18) I1A 0.0765(8) 0.0538(4) 0.0851(8) 0.0358(5) 0.0656(7) 0.0208(5) I2A 0.0318(3) 0.0501(4) 0.0491(5) 0.0109(3) 0.0171(2) 0.0115(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 I2 C17 2.081(7) . ? Cu4 Cu4 2.6053(12) 5_666 ? Cu4 O6 1.964(4) . ? Cu4 O5 1.973(4) . ? Cu4 N1 2.168(4) . ? Cu4 O3 1.962(4) 5_666 ? Cu4 O8 1.965(4) 5_666 ? I1 C23 2.115(8) . ? O6 C38 1.254(7) . ? O5 C10 1.260(7) . ? N1 C8 1.330(7) . ? N1 C9 1.334(6) . ? O3 Cu4 1.962(4) 5_666 ? O3 C10 1.259(7) . ? C7 C13 1.393(8) . ? C7 C16 1.384(9) . ? C7 C38 1.497(8) . ? C8 C24 1.374(7) . ? C9 N1 1.334(6) 2_656 ? C10 C14 1.494(8) . ? C11 C14 1.402(9) . ? C11 C23 1.385(10) . ? C12 C14 1.396(9) . ? C12 C37 1.392(10) . ? C13 C18 1.388(9) . ? C16 C17 1.387(9) . ? C17 C25 1.393(10) . ? C17 I2A 2.381(17) . ? C18 C25 1.372(12) . ? C23 C34 1.419(13) . ? C23 I1A 1.904(8) . ? C24 C8 1.374(7) 2_656 ? C34 C37 1.395(13) . ? C38 O8 1.262(6) . ? O7 C39 1.403(12) . ? O8 Cu4 1.965(4) 5_666 ? 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 Cu4 Cu4 84.56(12) . 5_666 ? O6 Cu4 O5 90.61(18) . . ? O6 Cu4 N1 96.73(17) . . ? O6 Cu4 O8 169.28(16) . 5_666 ? O5 Cu4 Cu4 82.78(12) . 5_666 ? O5 Cu4 N1 94.24(17) . . ? N1 Cu4 Cu4 176.78(13) . 5_666 ? O3 Cu4 Cu4 86.44(12) 5_666 5_666 ? O3 Cu4 O6 88.50(19) 5_666 . ? O3 Cu4 O5 169.22(17) 5_666 . ? O3 Cu4 N1 96.53(17) 5_666 . ? O3 Cu4 O8 90.89(19) 5_666 5_666 ? O8 Cu4 Cu4 84.72(12) 5_666 5_666 ? O8 Cu4 O5 87.99(19) 5_666 . ? O8 Cu4 N1 93.97(17) 5_666 . ? C38 O6 Cu4 122.7(3) . . ? C10 O5 Cu4 124.6(4) . . ? C8 N1 Cu4 119.1(4) . . ? C8 N1 C9 116.5(5) . . ? C9 N1 Cu4 124.4(4) . . ? C10 O3 Cu4 121.0(3) . 5_666 ? C13 C7 C38 121.0(6) . . ? C16 C7 C13 118.5(6) . . ? C16 C7 C38 120.4(5) . . ? N1 C8 C24 122.5(6) . . ? N1 C9 N1 125.5(7) 2_656 . ? O5 C10 C14 117.1(5) . . ? O3 C10 O5 125.1(5) . . ? O3 C10 C14 117.8(5) . . ? C23 C11 C14 119.9(7) . . ? C37 C12 C14 119.1(7) . . ? C18 C13 C7 120.0(7) . . ? C11 C14 C10 119.5(6) . . ? C12 C14 C10 119.6(6) . . ? C12 C14 C11 120.8(6) . . ? C7 C16 C17 120.9(6) . . ? I2 C17 I2A 13.3(4) . . ? C16 C17 I2 119.3(5) . . ? C16 C17 C25 120.8(7) . . ? C16 C17 I2A 109.5(6) . . ? C25 C17 I2 119.9(5) . . ? C25 C17 I2A 128.3(6) . . ? C25 C18 C13 121.9(6) . . ? C11 C23 I1 119.7(7) . . ? C11 C23 C34 119.5(7) . . ? C11 C23 I1A 128.7(7) . . ? C34 C23 I1 120.8(5) . . ? C34 C23 I1A 108.8(6) . . ? I1A C23 I1 20.8(2) . . ? C8 C24 C8 116.6(8) 2_656 . ? C18 C25 C17 118.0(6) . . ? C37 C34 C23 119.7(7) . . ? C12 C37 C34 120.7(8) . . ? O6 C38 C7 117.1(5) . . ? O6 C38 O8 125.7(5) . . ? O8 C38 C7 117.2(5) . . ? C38 O8 Cu4 122.2(4) . 5_666 ? data_ilb1205_0m _database_code_depnum_ccdc_archive 'CCDC 911301' #TrackingRef '2_DMP.cif' _audit_creation_date 2011-06-24 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C20 H16 Cu I2 N2 O4)' _chemical_formula_sum 'C40 H32 Cu2 I4 N4 O8' _chemical_formula_weight 1331.38 _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 10.4450(11) _cell_length_b 10.5713(11) _cell_length_c 12.0695(12) _cell_angle_alpha 64.728(6) _cell_angle_beta 82.156(7) _cell_angle_gamma 67.008(6) _cell_volume 1108.7(2) _cell_formula_units_Z 1 _cell_measurement_reflns_used 5259 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 26.183 _cell_measurement_theta_min 2.294 _exptl_absorpt_coefficient_mu 3.797 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.769358 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0411 before and 0.0292 after correction. The Ratio of minimum to maximum transmission is 0.769358. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour '? ? green' _exptl_crystal_colour_lustre ? _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.994 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 634 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.09 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_unetI/netI 0.0400 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 15423 _diffrn_reflns_theta_full 26.42 _diffrn_reflns_theta_max 26.42 _diffrn_reflns_theta_min 1.87 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _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 3727 _reflns_number_total 4491 _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 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.889 _refine_diff_density_min -1.408 _refine_diff_density_rms 0.125 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.820 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 4491 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0341 _refine_ls_restrained_S_all 0.820 _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.1125 _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. ; _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 I3 I 0.28536(4) 0.89988(4) 1.61332(3) 0.03530(13) Uani 1 1 d . . . Cu1 Cu 0.10461(5) 0.87011(6) 1.04861(5) 0.01604(15) Uani 1 1 d . . . I13 I 0.21757(4) 1.57067(4) 0.41925(3) 0.03017(13) Uani 1 1 d . . . O12 O -0.0312(3) 0.7907(4) 1.1561(3) 0.0217(7) Uani 1 1 d . . . O11 O 0.2111(3) 0.9903(4) 0.9334(3) 0.0224(7) Uani 1 1 d . . . O1 O 0.1294(3) 0.9352(4) 1.1726(3) 0.0247(7) Uani 1 1 d . . . O2 O 0.0431(3) 0.8398(4) 0.9170(3) 0.0238(7) Uani 1 1 d . . . N24 N 0.2854(4) 0.6610(4) 1.0988(3) 0.0186(8) Uani 1 1 d . . . N21 N 0.5170(4) 0.3933(5) 1.1686(4) 0.0256(9) Uani 1 1 d . . . C25 C 0.4106(5) 0.6560(5) 1.1163(4) 0.0224(10) Uani 1 1 d . . . H25 H 0.4206 0.7442 1.1054 0.027 Uiso 1 1 calc R . . C13 C 0.2970(5) 1.3766(5) 0.5820(4) 0.0212(10) Uani 1 1 d . . . C23 C 0.2759(5) 0.5310(5) 1.1169(4) 0.0228(10) Uani 1 1 d . . . H23 H 0.1897 0.5300 1.1067 0.027 Uiso 1 1 calc R . . C7 C 0.0527(5) 1.0672(5) 1.1630(4) 0.0197(9) Uani 1 1 d . . . C26 C 0.5268(5) 0.5228(6) 1.1505(5) 0.0239(10) Uani 1 1 d . . . C17 C 0.1591(5) 1.1245(5) 0.8567(4) 0.0202(10) Uani 1 1 d . . . C22 C 0.3922(5) 0.3970(5) 1.1505(4) 0.0234(10) Uani 1 1 d . . . C15 C 0.4913(5) 1.1799(6) 0.7163(5) 0.0309(12) Uani 1 1 d . . . H15 H 0.5867 1.1328 0.7340 0.037 Uiso 1 1 calc R . . C2 C 0.1511(5) 1.0129(6) 1.3635(4) 0.0239(10) Uani 1 1 d . . . H2 H 0.1865 0.9106 1.3809 0.029 Uiso 1 1 calc R . . C1 C 0.0779(5) 1.1159(6) 1.2549(4) 0.0232(10) Uani 1 1 d . . . C12 C 0.2065(5) 1.3194(5) 0.6636(4) 0.0216(10) Uani 1 1 d . . . H12 H 0.1111 1.3674 0.6465 0.026 Uiso 1 1 calc R . . C3 C 0.1719(5) 1.0613(6) 1.4469(5) 0.0288(11) Uani 1 1 d . . . C11 C 0.2575(5) 1.1898(5) 0.7716(4) 0.0208(10) Uani 1 1 d . . . C14 C 0.4416(5) 1.3069(6) 0.6081(5) 0.0295(11) Uani 1 1 d . . . H14 H 0.5027 1.3455 0.5537 0.035 Uiso 1 1 calc R . . C4 C 0.1215(5) 1.2151(6) 1.4216(5) 0.0325(12) Uani 1 1 d . . . H4 H 0.1355 1.2471 1.4781 0.039 Uiso 1 1 calc R . . C16 C 0.4013(5) 1.1218(6) 0.7986(5) 0.0244(10) Uani 1 1 d . . . H16 H 0.4362 1.0378 0.8716 0.029 Uiso 1 1 calc R . . C28 C 0.6681(5) 0.5177(6) 1.1700(6) 0.0358(13) Uani 1 1 d . . . H28A H 0.6916 0.4698 1.2561 0.043 Uiso 1 1 calc R . . H28B H 0.6669 0.6184 1.1370 0.043 Uiso 1 1 calc R . . H28C H 0.7359 0.4616 1.1292 0.043 Uiso 1 1 calc R . . C27 C 0.3839(6) 0.2497(6) 1.1702(6) 0.0420(14) Uani 1 1 d . . . H27A H 0.4672 0.1918 1.1426 0.050 Uiso 1 1 calc R . . H27B H 0.3048 0.2692 1.1246 0.050 Uiso 1 1 calc R . . H27C H 0.3744 0.1945 1.2558 0.050 Uiso 1 1 calc R . . C6 C 0.0275(5) 1.2715(6) 1.2266(5) 0.0293(11) Uani 1 1 d . . . H6 H -0.0205 1.3419 1.1527 0.035 Uiso 1 1 calc R . . C5 C 0.0511(6) 1.3177(7) 1.3119(6) 0.0389(14) Uani 1 1 d . . . H5 H 0.0185 1.4200 1.2940 0.047 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 I3 0.0376(2) 0.0409(2) 0.0238(2) -0.01337(18) -0.00690(15) -0.00836(17) Cu1 0.0161(3) 0.0150(3) 0.0148(3) -0.0059(2) -0.0012(2) -0.0032(2) I13 0.0371(2) 0.0323(2) 0.0193(2) -0.00486(16) 0.00206(14) -0.01778(16) O12 0.0193(16) 0.0181(17) 0.0206(18) -0.0026(14) 0.0007(13) -0.0058(14) O11 0.0201(16) 0.0199(18) 0.0215(18) -0.0044(15) 0.0006(13) -0.0061(14) O1 0.0288(18) 0.0239(19) 0.0212(18) -0.0114(16) -0.0038(14) -0.0054(15) O2 0.0232(17) 0.0244(18) 0.0235(18) -0.0122(16) -0.0038(14) -0.0044(14) N24 0.0217(19) 0.018(2) 0.0125(19) -0.0035(16) -0.0031(15) -0.0060(16) N21 0.022(2) 0.023(2) 0.023(2) -0.0088(19) -0.0008(17) -0.0005(17) C25 0.022(2) 0.023(3) 0.023(3) -0.011(2) 0.0014(19) -0.008(2) C13 0.025(2) 0.021(2) 0.019(2) -0.009(2) 0.0045(19) -0.010(2) C23 0.023(2) 0.022(3) 0.022(3) -0.008(2) -0.0026(19) -0.007(2) C7 0.017(2) 0.025(3) 0.019(2) -0.011(2) 0.0012(18) -0.007(2) C26 0.019(2) 0.025(3) 0.027(3) -0.014(2) -0.0038(19) -0.003(2) C17 0.030(3) 0.022(3) 0.016(2) -0.010(2) -0.0017(19) -0.012(2) C22 0.023(2) 0.016(2) 0.024(3) -0.008(2) -0.0010(19) 0.000(2) C15 0.024(3) 0.029(3) 0.038(3) -0.015(3) 0.003(2) -0.007(2) C2 0.024(2) 0.024(3) 0.025(3) -0.012(2) 0.0024(19) -0.009(2) C1 0.017(2) 0.030(3) 0.023(3) -0.014(2) -0.0006(18) -0.006(2) C12 0.025(2) 0.024(3) 0.020(2) -0.014(2) 0.0002(19) -0.007(2) C3 0.029(3) 0.034(3) 0.023(3) -0.015(2) 0.000(2) -0.007(2) C11 0.025(2) 0.020(2) 0.020(2) -0.009(2) 0.0041(19) -0.011(2) C14 0.035(3) 0.029(3) 0.029(3) -0.014(2) 0.004(2) -0.015(2) C4 0.034(3) 0.037(3) 0.032(3) -0.025(3) -0.005(2) -0.004(2) C16 0.019(2) 0.021(3) 0.026(3) -0.009(2) -0.0013(19) -0.001(2) C28 0.020(3) 0.036(3) 0.051(4) -0.025(3) -0.008(2) 0.001(2) C27 0.039(3) 0.024(3) 0.060(4) -0.015(3) -0.006(3) -0.008(3) C6 0.023(2) 0.029(3) 0.034(3) -0.015(3) -0.001(2) -0.004(2) C5 0.046(3) 0.028(3) 0.046(4) -0.024(3) -0.001(3) -0.007(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I3 C3 2.120(5) . ? Cu1 Cu1 2.6371(11) 2_577 ? Cu1 O12 1.975(3) . ? Cu1 O11 1.990(3) . ? Cu1 O1 1.975(3) . ? Cu1 O2 1.978(3) . ? Cu1 N24 2.174(4) . ? I13 C13 2.105(5) . ? O12 C17 1.271(6) 2_577 ? O11 C17 1.257(6) . ? O1 C7 1.272(6) . ? O2 C7 1.259(6) 2_577 ? N24 C25 1.330(6) . ? N24 C23 1.338(6) . ? N21 C26 1.334(6) . ? N21 C22 1.334(6) . ? C25 C26 1.390(7) . ? C13 C12 1.383(6) . ? C13 C14 1.410(7) . ? C23 C22 1.395(7) . ? C7 O2 1.259(6) 2_577 ? C7 C1 1.496(6) . ? C26 C28 1.502(7) . ? C17 O12 1.271(6) 2_577 ? C17 C11 1.499(6) . ? C22 C27 1.507(7) . ? C15 C14 1.386(8) . ? C15 C16 1.387(7) . ? C2 C1 1.376(7) . ? C2 C3 1.381(7) . ? C1 C6 1.412(7) . ? C12 C11 1.399(7) . ? C3 C4 1.402(7) . ? C11 C16 1.403(6) . ? C4 C5 1.374(8) . ? C6 C5 1.396(7) . ? 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 O12 Cu1 Cu1 87.27(10) . 2_577 ? O12 Cu1 O11 168.47(13) . . ? O12 Cu1 O1 88.07(14) . . ? O12 Cu1 O2 88.63(14) . . ? O12 Cu1 N24 98.77(13) . . ? O11 Cu1 Cu1 81.58(10) . 2_577 ? O11 Cu1 N24 92.65(13) . . ? O1 Cu1 Cu1 88.03(10) . 2_577 ? O1 Cu1 O11 88.67(14) . . ? O1 Cu1 O2 168.34(13) . . ? O1 Cu1 N24 98.93(13) . . ? O2 Cu1 Cu1 80.64(10) . 2_577 ? O2 Cu1 O11 92.37(14) . . ? O2 Cu1 N24 92.62(13) . . ? N24 Cu1 Cu1 170.89(10) . 2_577 ? C17 O12 Cu1 119.3(3) 2_577 . ? C17 O11 Cu1 125.5(3) . . ? C7 O1 Cu1 118.4(3) . . ? C7 O2 Cu1 127.3(3) 2_577 . ? C25 N24 Cu1 121.1(3) . . ? C25 N24 C23 116.8(4) . . ? C23 N24 Cu1 122.0(3) . . ? C22 N21 C26 117.5(4) . . ? N24 C25 C26 121.9(4) . . ? C12 C13 I13 119.7(4) . . ? C12 C13 C14 120.4(5) . . ? C14 C13 I13 119.9(4) . . ? N24 C23 C22 121.6(4) . . ? O1 C7 C1 117.3(4) . . ? O2 C7 O1 125.5(4) 2_577 . ? O2 C7 C1 117.2(4) 2_577 . ? N21 C26 C25 121.1(4) . . ? N21 C26 C28 117.1(4) . . ? C25 C26 C28 121.7(4) . . ? O12 C17 C11 117.1(4) 2_577 . ? O11 C17 O12 126.2(4) . 2_577 ? O11 C17 C11 116.7(4) . . ? N21 C22 C23 121.0(4) . . ? N21 C22 C27 116.6(4) . . ? C23 C22 C27 122.4(4) . . ? C14 C15 C16 121.1(5) . . ? C1 C2 C3 120.0(5) . . ? C2 C1 C7 121.4(4) . . ? C2 C1 C6 120.2(4) . . ? C6 C1 C7 118.4(4) . . ? C13 C12 C11 120.4(4) . . ? C2 C3 I3 119.1(4) . . ? C2 C3 C4 120.9(5) . . ? C4 C3 I3 120.0(4) . . ? C12 C11 C17 120.0(4) . . ? C12 C11 C16 119.2(4) . . ? C16 C11 C17 120.8(4) . . ? C15 C14 C13 118.9(5) . . ? C5 C4 C3 118.9(5) . . ? C15 C16 C11 120.0(5) . . ? C5 C6 C1 118.7(5) . . ? C4 C5 C6 121.3(5) . . ? data_ilb1203_0m _database_code_depnum_ccdc_archive 'CCDC 911302' #TrackingRef '3_3CN.cif' _audit_creation_date 2011-06-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety '2(C20 H12 Cu I2 N2 O4), 2(C H2 Cl2)' _chemical_formula_sum 'C42 H28 Cl4 Cu2 I4 N4 O8' _chemical_formula_weight 1493.16 _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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 11.2066(3) _cell_length_b 17.1224(4) _cell_length_c 12.7046(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.758(2) _cell_angle_gamma 90.00 _cell_volume 2420.87(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9080 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 27.422 _cell_measurement_theta_min 2.583 _exptl_absorpt_coefficient_mu 3.704 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.764219 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0690 before and 0.0294 after correction. The Ratio of minimum to maximum transmission is 0.764219. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour 'clear ? green' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 2.048 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1420 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.2 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_unetI/netI 0.0224 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 44684 _diffrn_reflns_theta_full 27.57 _diffrn_reflns_theta_max 27.57 _diffrn_reflns_theta_min 1.83 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _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 4920 _reflns_number_total 5593 _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 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.940 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.099 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 5593 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0328 _refine_ls_R_factor_gt 0.0268 _refine_ls_restrained_S_all 1.055 _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^)+(0.0251P)^2^+4.8029P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.0631 _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. ; _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 I3 I 0.70952(2) 0.092736(12) 0.393938(17) 0.02514(6) Uani 1 1 d . . . I13 I 0.60589(2) 0.620899(13) 0.929236(17) 0.02985(7) Uani 1 1 d . . . Cu1 Cu 0.98627(3) 0.546212(19) 0.41739(3) 0.01316(8) Uani 1 1 d . . . Cl1S Cl 0.36787(10) 0.36870(6) 0.76954(9) 0.0463(2) Uani 1 1 d . . . Cl2S Cl 0.44902(14) 0.48533(9) 0.62823(10) 0.0768(5) Uani 1 1 d . . . O12 O 0.84604(19) 0.58737(12) 0.47943(16) 0.0199(4) Uani 1 1 d . . . O1 O 1.0857(2) 0.61952(12) 0.51054(16) 0.0205(4) Uani 1 1 d . . . O2 O 0.8884(2) 0.46002(12) 0.34898(16) 0.0213(5) Uani 1 1 d . . . O11 O 1.1296(2) 0.49268(12) 0.38011(16) 0.0216(5) Uani 1 1 d . . . N21 N 0.9638(2) 0.62197(13) 0.28128(18) 0.0150(5) Uani 1 1 d . . . C11 C 0.7202(3) 0.60378(16) 0.6144(2) 0.0170(6) Uani 1 1 d . . . N28 N 0.9579(3) 0.59293(17) -0.0934(2) 0.0301(7) Uani 1 1 d . . . C7 C 0.8759(3) 0.39582(16) 0.3951(2) 0.0160(6) Uani 1 1 d . . . C23 C 0.9419(3) 0.64551(17) 0.0952(2) 0.0164(6) Uani 1 1 d . . . C12 C 0.7093(3) 0.59277(16) 0.7218(2) 0.0171(6) Uani 1 1 d . . . H12 H 0.7614 0.5580 0.7634 0.021 Uiso 1 1 calc R . . C25 C 0.9179(3) 0.75057(17) 0.2135(2) 0.0218(6) Uani 1 1 d . . . H25 H 0.9023 0.8039 0.2271 0.026 Uiso 1 1 calc R . . C26 C 0.9426(3) 0.69834(17) 0.2961(2) 0.0194(6) Uani 1 1 d . . . H26 H 0.9447 0.7172 0.3666 0.023 Uiso 1 1 calc R . . C27 C 0.9491(3) 0.61558(18) -0.0100(2) 0.0212(6) Uani 1 1 d . . . C22 C 0.9645(3) 0.59618(16) 0.1823(2) 0.0157(6) Uani 1 1 d . . . H22 H 0.9810 0.5426 0.1709 0.019 Uiso 1 1 calc R . . C6 C 0.7293(3) 0.27688(19) 0.1625(2) 0.0249(7) Uani 1 1 d . . . H6 H 0.7066 0.2829 0.0886 0.030 Uiso 1 1 calc R . . C16 C 0.6444(3) 0.65573(18) 0.5546(3) 0.0223(6) Uani 1 1 d . . . H16 H 0.6540 0.6648 0.4823 0.027 Uiso 1 1 calc R . . C5 C 0.7812(3) 0.33966(18) 0.2213(2) 0.0217(6) Uani 1 1 d . . . H5 H 0.7951 0.3877 0.1873 0.026 Uiso 1 1 calc R . . C13 C 0.6210(3) 0.63357(18) 0.7663(2) 0.0219(6) Uani 1 1 d . . . C14 C 0.5433(3) 0.68346(19) 0.7068(3) 0.0278(7) Uani 1 1 d . . . H14 H 0.4823 0.7102 0.7384 0.033 Uiso 1 1 calc R . . C2 C 0.7921(3) 0.26059(17) 0.3794(2) 0.0192(6) Uani 1 1 d . . . H2 H 0.8128 0.2548 0.4537 0.023 Uiso 1 1 calc R . . C15 C 0.5551(3) 0.6942(2) 0.6004(3) 0.0288(7) Uani 1 1 d . . . H15 H 0.5015 0.7281 0.5587 0.035 Uiso 1 1 calc R . . C17 C 0.8191(3) 0.56256(17) 0.5675(2) 0.0162(6) Uani 1 1 d . . . C24 C 0.9164(3) 0.72400(17) 0.1114(2) 0.0202(6) Uani 1 1 d . . . H24 H 0.8984 0.7584 0.0531 0.024 Uiso 1 1 calc R . . C1 C 0.8126(3) 0.33132(17) 0.3302(2) 0.0183(6) Uani 1 1 d . . . C3 C 0.7413(3) 0.19889(17) 0.3197(2) 0.0201(6) Uani 1 1 d . . . C4 C 0.7103(3) 0.20621(19) 0.2103(3) 0.0251(7) Uani 1 1 d . . . H4 H 0.6767 0.1633 0.1696 0.030 Uiso 1 1 calc R . . C1S C 0.3744(4) 0.4683(2) 0.7389(4) 0.0508(11) Uani 1 1 d . . . H1SA H 0.2917 0.4892 0.7253 0.061 Uiso 1 1 calc R . . H1SB H 0.4162 0.4965 0.8005 0.061 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 I3 0.02980(12) 0.01785(11) 0.02817(12) -0.00162(8) 0.00512(9) -0.00458(8) I13 0.03629(14) 0.03227(13) 0.02337(11) -0.00502(8) 0.01350(9) 0.00349(10) Cu1 0.01800(18) 0.01116(16) 0.01065(16) 0.00137(12) 0.00305(13) 0.00120(13) Cl1S 0.0423(6) 0.0453(6) 0.0496(6) 0.0095(4) -0.0019(5) -0.0042(5) Cl2S 0.0970(11) 0.0776(9) 0.0532(7) 0.0041(6) -0.0023(7) -0.0584(8) O12 0.0218(11) 0.0215(11) 0.0178(10) 0.0044(8) 0.0077(9) 0.0061(9) O1 0.0271(12) 0.0158(10) 0.0180(10) 0.0009(8) -0.0002(9) -0.0039(9) O2 0.0281(12) 0.0149(10) 0.0200(11) 0.0013(8) -0.0016(9) -0.0041(9) O11 0.0270(12) 0.0220(11) 0.0169(10) 0.0036(8) 0.0075(9) 0.0074(9) N21 0.0177(12) 0.0143(12) 0.0134(11) 0.0034(9) 0.0033(10) 0.0018(10) C11 0.0149(14) 0.0145(14) 0.0220(15) -0.0017(11) 0.0037(12) -0.0018(11) N28 0.0375(17) 0.0341(16) 0.0184(14) 0.0003(11) 0.0020(12) 0.0034(13) C7 0.0163(14) 0.0147(14) 0.0171(14) -0.0010(11) 0.0027(11) 0.0020(11) C23 0.0184(15) 0.0185(14) 0.0124(13) -0.0004(11) 0.0021(11) -0.0007(12) C12 0.0171(15) 0.0149(14) 0.0196(14) -0.0028(11) 0.0033(12) -0.0012(11) C25 0.0309(17) 0.0124(14) 0.0226(15) 0.0036(11) 0.0057(13) 0.0054(13) C26 0.0278(17) 0.0176(14) 0.0134(13) 0.0000(11) 0.0056(12) 0.0029(12) C27 0.0255(17) 0.0218(15) 0.0159(15) 0.0017(12) 0.0012(12) -0.0005(13) C22 0.0194(15) 0.0120(13) 0.0159(14) 0.0005(10) 0.0034(11) -0.0007(11) C6 0.0303(18) 0.0275(17) 0.0168(15) -0.0011(12) 0.0024(13) 0.0014(14) C16 0.0206(16) 0.0238(16) 0.0234(16) 0.0047(12) 0.0055(13) 0.0013(13) C5 0.0250(17) 0.0198(15) 0.0208(15) -0.0005(12) 0.0045(13) 0.0027(13) C13 0.0248(16) 0.0183(15) 0.0243(16) -0.0039(12) 0.0099(13) -0.0036(13) C14 0.0268(18) 0.0212(16) 0.0385(19) -0.0005(14) 0.0163(15) 0.0064(14) C2 0.0196(15) 0.0206(15) 0.0179(14) -0.0016(11) 0.0038(12) 0.0007(12) C15 0.0260(18) 0.0260(17) 0.0351(19) 0.0084(14) 0.0063(15) 0.0065(14) C17 0.0162(14) 0.0155(14) 0.0171(14) -0.0026(11) 0.0027(11) -0.0024(11) C24 0.0251(16) 0.0173(14) 0.0182(14) 0.0067(11) 0.0022(12) 0.0028(12) C1 0.0175(15) 0.0171(14) 0.0206(15) -0.0019(11) 0.0031(12) 0.0011(12) C3 0.0211(16) 0.0163(14) 0.0239(15) 0.0005(12) 0.0067(12) -0.0004(12) C4 0.0245(17) 0.0199(15) 0.0312(17) -0.0077(13) 0.0047(14) -0.0012(13) C1S 0.057(3) 0.037(2) 0.054(3) -0.0028(19) -0.014(2) 0.008(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 I3 C3 2.098(3) . ? I13 C13 2.108(3) . ? Cu1 Cu1 2.6180(6) 3_766 ? Cu1 O12 1.970(2) . ? Cu1 O1 1.977(2) . ? Cu1 O2 1.978(2) . ? Cu1 O11 1.955(2) . ? Cu1 N21 2.153(2) . ? Cl1S C1S 1.752(4) . ? Cl2S C1S 1.742(5) . ? O12 C17 1.266(3) . ? O1 C7 1.253(4) 3_766 ? O2 C7 1.261(3) . ? O11 C17 1.256(4) 3_766 ? N21 C26 1.346(4) . ? N21 C22 1.334(4) . ? C11 C12 1.397(4) . ? C11 C16 1.392(4) . ? C11 C17 1.495(4) . ? N28 C27 1.143(4) . ? C7 O1 1.253(4) 3_766 ? C7 C1 1.505(4) . ? C23 C27 1.442(4) . ? C23 C22 1.391(4) . ? C23 C24 1.394(4) . ? C12 C13 1.385(4) . ? C25 C26 1.382(4) . ? C25 C24 1.373(4) . ? C6 C5 1.396(4) . ? C6 C4 1.381(5) . ? C16 C15 1.382(5) . ? C5 C1 1.394(4) . ? C13 C14 1.381(5) . ? C14 C15 1.386(5) . ? C2 C1 1.394(4) . ? C2 C3 1.383(4) . ? C17 O11 1.256(4) 3_766 ? C3 C4 1.397(5) . ? 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 O12 Cu1 Cu1 85.38(6) . 3_766 ? O12 Cu1 O1 87.33(9) . . ? O12 Cu1 O2 90.90(9) . . ? O12 Cu1 N21 94.73(9) . . ? O1 Cu1 Cu1 84.20(6) . 3_766 ? O1 Cu1 O2 168.89(8) . . ? O1 Cu1 N21 95.89(9) . . ? O2 Cu1 Cu1 84.73(6) . 3_766 ? O2 Cu1 N21 95.18(9) . . ? O11 Cu1 Cu1 83.59(6) . 3_766 ? O11 Cu1 O12 168.97(8) . . ? O11 Cu1 O1 91.22(9) . . ? O11 Cu1 O2 88.42(9) . . ? O11 Cu1 N21 96.30(9) . . ? N21 Cu1 Cu1 179.85(7) . 3_766 ? C17 O12 Cu1 121.18(19) . . ? C7 O1 Cu1 123.05(19) 3_766 . ? C7 O2 Cu1 122.17(19) . . ? C17 O11 Cu1 124.21(19) 3_766 . ? C26 N21 Cu1 118.60(19) . . ? C22 N21 Cu1 123.01(19) . . ? C22 N21 C26 118.3(2) . . ? C12 C11 C17 118.6(3) . . ? C16 C11 C12 120.0(3) . . ? C16 C11 C17 121.2(3) . . ? O1 C7 O2 125.7(3) 3_766 . ? O1 C7 C1 117.2(3) 3_766 . ? O2 C7 C1 117.1(3) . . ? C22 C23 C27 119.8(3) . . ? C22 C23 C24 119.2(3) . . ? C24 C23 C27 121.0(3) . . ? C13 C12 C11 118.7(3) . . ? C24 C25 C26 118.8(3) . . ? N21 C26 C25 123.0(3) . . ? N28 C27 C23 178.0(4) . . ? N21 C22 C23 121.9(3) . . ? C4 C6 C5 121.1(3) . . ? C15 C16 C11 120.1(3) . . ? C1 C5 C6 119.5(3) . . ? C12 C13 I13 119.6(2) . . ? C14 C13 I13 118.9(2) . . ? C14 C13 C12 121.6(3) . . ? C13 C14 C15 119.3(3) . . ? C3 C2 C1 119.8(3) . . ? C16 C15 C14 120.3(3) . . ? O12 C17 C11 117.3(3) . . ? O11 C17 O12 125.4(3) 3_766 . ? O11 C17 C11 117.3(3) 3_766 . ? C25 C24 C23 118.7(3) . . ? C5 C1 C7 121.1(3) . . ? C2 C1 C7 118.9(3) . . ? C2 C1 C5 119.9(3) . . ? C2 C3 I3 119.7(2) . . ? C2 C3 C4 121.0(3) . . ? C4 C3 I3 119.3(2) . . ? C6 C4 C3 118.8(3) . . ? Cl2S C1S Cl1S 112.3(3) . . ? data_ilb1204_0m _database_code_depnum_ccdc_archive 'CCDC 911303' #TrackingRef '4_4CN.cif' _audit_creation_date 2011-06-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C20 H12 Cu I2 N2 O4)' _chemical_formula_sum 'C40 H24 Cu2 I4 N4 O8' _chemical_formula_weight 1323.31 _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 9.7650(9) _cell_length_b 9.9384(8) _cell_length_c 11.6831(10) _cell_angle_alpha 73.381(5) _cell_angle_beta 80.448(5) _cell_angle_gamma 84.369(5) _cell_volume 1069.86(16) _cell_formula_units_Z 1 _cell_measurement_reflns_used 7605 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 27.497 _cell_measurement_theta_min 2.409 _exptl_absorpt_coefficient_mu 3.934 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.672747 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.1149 before and 0.0401 after correction. The Ratio of minimum to maximum transmission is 0.672747. 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 2.054 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 626 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.19 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0410 _diffrn_reflns_av_unetI/netI 0.0304 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 31449 _diffrn_reflns_theta_full 27.65 _diffrn_reflns_theta_max 27.65 _diffrn_reflns_theta_min 1.84 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _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 4074 _reflns_number_total 4921 _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 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.779 _refine_diff_density_min -1.560 _refine_diff_density_rms 0.138 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 262 _refine_ls_number_reflns 4921 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0394 _refine_ls_restrained_S_all 1.026 _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^)+(0.0481P)^2^+4.0080P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0995 _refine_ls_wR_factor_ref 0.1047 _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. ; _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 I3 I 0.53727(4) -0.31693(4) -0.02629(3) 0.04388(12) Uani 1 1 d . . . Cu1 Cu 0.55889(5) 0.12048(5) 0.47201(5) 0.02019(13) Uani 1 1 d . . . I13 I 0.06815(5) 0.60968(4) 0.11862(3) 0.04838(13) Uani 1 1 d . . . O2 O 0.4715(3) 0.1177(3) 0.6374(3) 0.0274(7) Uani 1 1 d . . . O1 O 0.6304(3) 0.0878(3) 0.3127(3) 0.0256(6) Uani 1 1 d . . . O12 O 0.7128(3) 0.0027(3) 0.5424(3) 0.0265(7) Uani 1 1 d . . . O11 O 0.3866(3) 0.2043(3) 0.4082(3) 0.0252(6) Uani 1 1 d . . . N21 N 0.6520(4) 0.3177(3) 0.4479(3) 0.0227(7) Uani 1 1 d . . . C11 C 0.1703(4) 0.1971(4) 0.3469(4) 0.0217(8) Uani 1 1 d . . . N29 N 0.9068(5) 0.7956(4) 0.3706(4) 0.0382(10) Uani 1 1 d . . . C12 C 0.1737(5) 0.3378(5) 0.2808(4) 0.0260(9) Uani 1 1 d . . . H12 H 0.2493 0.3899 0.2771 0.031 Uiso 1 1 calc R . . C24 C 0.7777(5) 0.5665(4) 0.4134(4) 0.0270(9) Uani 1 1 d . . . C13 C 0.0625(5) 0.3990(5) 0.2207(4) 0.0297(10) Uani 1 1 d . . . C25 C 0.8080(5) 0.4497(5) 0.5050(4) 0.0306(10) Uani 1 1 d . . . H25 H 0.8701 0.4536 0.5562 0.037 Uiso 1 1 calc R . . C1 C 0.6496(5) -0.0409(5) 0.1673(4) 0.0273(9) Uani 1 1 d . . . C28 C 0.8485(5) 0.6960(5) 0.3907(4) 0.0294(10) Uani 1 1 d . . . C2 C 0.5835(5) -0.1371(5) 0.1298(4) 0.0281(9) Uani 1 1 d . . . H2 H 0.5063 -0.1819 0.1781 0.034 Uiso 1 1 calc R . . C16 C 0.0569(5) 0.1196(5) 0.3513(4) 0.0272(9) Uani 1 1 d . . . H16 H 0.0557 0.0251 0.3942 0.033 Uiso 1 1 calc R . . C7 C 0.5994(4) -0.0212(4) 0.2899(4) 0.0246(9) Uani 1 1 d . . . C17 C 0.2906(4) 0.1277(4) 0.4098(4) 0.0226(8) Uani 1 1 d . . . C3 C 0.6338(5) -0.1645(5) 0.0212(4) 0.0318(10) Uani 1 1 d . . . C15 C -0.0531(5) 0.1828(5) 0.2923(4) 0.0330(10) Uani 1 1 d . . . H15 H -0.1294 0.1313 0.2972 0.040 Uiso 1 1 calc R . . C26 C 0.7441(5) 0.3275(5) 0.5189(4) 0.0289(10) Uani 1 1 d . . . H26 H 0.7653 0.2484 0.5799 0.035 Uiso 1 1 calc R . . C22 C 0.6219(5) 0.4317(5) 0.3621(5) 0.0347(11) Uani 1 1 d . . . H22 H 0.5567 0.4263 0.3140 0.042 Uiso 1 1 calc R . . C6 C 0.7607(6) 0.0288(5) 0.0912(5) 0.0411(13) Uani 1 1 d . . . H6 H 0.8015 0.0967 0.1131 0.049 Uiso 1 1 calc R . . C14 C -0.0512(5) 0.3226(6) 0.2254(4) 0.0350(11) Uani 1 1 d . . . H14 H -0.1249 0.3647 0.1843 0.042 Uiso 1 1 calc R . . C4 C 0.7457(6) -0.0981(6) -0.0542(5) 0.0424(13) Uani 1 1 d . . . H4 H 0.7765 -0.1171 -0.1280 0.051 Uiso 1 1 calc R . . C23 C 0.6823(6) 0.5573(5) 0.3408(5) 0.0395(12) Uani 1 1 d . . . H23 H 0.6595 0.6347 0.2789 0.047 Uiso 1 1 calc R . . C5 C 0.8123(7) -0.0019(6) -0.0186(6) 0.0478(14) Uani 1 1 d . . . H5 H 0.8901 0.0415 -0.0671 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 I3 0.0507(2) 0.0484(2) 0.0425(2) -0.02549(16) -0.00617(16) -0.01200(16) Cu1 0.0211(3) 0.0176(2) 0.0241(3) -0.00823(19) -0.0017(2) -0.00678(18) I13 0.0679(3) 0.03134(18) 0.0394(2) -0.00256(14) -0.00708(18) 0.00556(16) O2 0.0337(18) 0.0255(15) 0.0256(16) -0.0110(12) -0.0008(13) -0.0080(13) O1 0.0268(16) 0.0255(14) 0.0272(16) -0.0110(12) -0.0008(13) -0.0082(12) O12 0.0271(16) 0.0206(14) 0.0330(17) -0.0061(12) -0.0072(13) -0.0059(12) O11 0.0217(15) 0.0228(14) 0.0330(17) -0.0083(12) -0.0053(13) -0.0062(12) N21 0.0222(18) 0.0190(16) 0.0289(19) -0.0080(14) -0.0037(15) -0.0059(14) C11 0.020(2) 0.0249(19) 0.022(2) -0.0104(16) 0.0005(16) -0.0063(16) N29 0.042(3) 0.027(2) 0.048(3) -0.0160(18) 0.002(2) -0.0128(18) C12 0.025(2) 0.028(2) 0.027(2) -0.0102(18) 0.0007(18) -0.0065(17) C24 0.026(2) 0.0173(18) 0.040(3) -0.0127(18) 0.0003(19) -0.0046(17) C13 0.033(3) 0.030(2) 0.025(2) -0.0084(18) -0.0009(19) -0.0003(19) C25 0.034(3) 0.027(2) 0.036(3) -0.0117(19) -0.010(2) -0.0089(19) C1 0.031(2) 0.027(2) 0.025(2) -0.0106(18) 0.0021(18) -0.0054(18) C28 0.030(2) 0.023(2) 0.037(3) -0.0125(19) -0.001(2) -0.0075(18) C2 0.030(2) 0.027(2) 0.028(2) -0.0079(18) -0.0040(19) -0.0024(18) C16 0.027(2) 0.034(2) 0.022(2) -0.0101(18) 0.0010(18) -0.0084(18) C7 0.021(2) 0.026(2) 0.029(2) -0.0116(17) -0.0022(17) -0.0030(17) C17 0.024(2) 0.0240(19) 0.021(2) -0.0086(16) 0.0010(17) -0.0049(16) C3 0.040(3) 0.025(2) 0.032(2) -0.0122(19) -0.005(2) -0.0020(19) C15 0.025(2) 0.047(3) 0.029(2) -0.012(2) -0.0025(19) -0.009(2) C26 0.036(3) 0.022(2) 0.029(2) -0.0045(17) -0.009(2) -0.0067(18) C22 0.034(3) 0.025(2) 0.048(3) -0.006(2) -0.019(2) -0.0074(19) C6 0.051(3) 0.037(3) 0.039(3) -0.017(2) 0.007(2) -0.022(2) C14 0.025(2) 0.051(3) 0.028(2) -0.010(2) -0.0042(19) -0.001(2) C4 0.054(4) 0.041(3) 0.034(3) -0.017(2) 0.005(2) -0.011(3) C23 0.042(3) 0.021(2) 0.056(3) -0.001(2) -0.022(3) -0.007(2) C5 0.053(4) 0.046(3) 0.049(3) -0.023(3) 0.009(3) -0.018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I3 C3 2.104(5) . ? Cu1 Cu1 2.6230(9) 2_656 ? Cu1 O2 1.973(3) . ? Cu1 O1 1.982(3) . ? Cu1 O12 1.955(3) . ? Cu1 O11 1.966(3) . ? Cu1 N21 2.167(3) . ? I13 C13 2.093(4) . ? O2 C7 1.261(5) 2_656 ? O1 C7 1.262(5) . ? O12 C17 1.258(5) 2_656 ? O11 C17 1.259(5) . ? N21 C26 1.348(6) . ? N21 C22 1.326(6) . ? C11 C12 1.391(6) . ? C11 C16 1.396(6) . ? C11 C17 1.494(6) . ? N29 C28 1.137(6) . ? C12 C13 1.387(7) . ? C24 C25 1.381(7) . ? C24 C28 1.457(6) . ? C24 C23 1.385(7) . ? C13 C14 1.390(7) . ? C25 C26 1.376(6) . ? C1 C2 1.406(6) . ? C1 C7 1.497(6) . ? C1 C6 1.387(7) . ? C2 C3 1.375(7) . ? C16 C15 1.374(7) . ? C7 O2 1.261(5) 2_656 ? C17 O12 1.258(5) 2_656 ? C3 C4 1.376(7) . ? C15 C14 1.385(7) . ? C22 C23 1.374(6) . ? C6 C5 1.404(8) . ? C4 C5 1.397(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 Cu1 81.95(9) . 2_656 ? O2 Cu1 O1 168.93(12) . . ? O2 Cu1 N21 91.65(13) . . ? O1 Cu1 Cu1 86.97(8) . 2_656 ? O1 Cu1 N21 99.42(13) . . ? O12 Cu1 Cu1 83.12(9) . 2_656 ? O12 Cu1 O2 87.85(13) . . ? O12 Cu1 O1 90.78(13) . . ? O12 Cu1 O11 168.89(12) . . ? O12 Cu1 N21 94.93(13) . . ? O11 Cu1 Cu1 85.78(8) . 2_656 ? O11 Cu1 O2 90.89(13) . . ? O11 Cu1 O1 88.34(13) . . ? O11 Cu1 N21 96.13(13) . . ? N21 Cu1 Cu1 173.37(10) . 2_656 ? C7 O2 Cu1 126.0(3) 2_656 . ? C7 O1 Cu1 119.6(3) . . ? C17 O12 Cu1 124.2(3) 2_656 . ? C17 O11 Cu1 120.5(3) . . ? C26 N21 Cu1 120.9(3) . . ? C22 N21 Cu1 121.2(3) . . ? C22 N21 C26 117.9(4) . . ? C12 C11 C16 120.1(4) . . ? C12 C11 C17 119.8(4) . . ? C16 C11 C17 120.0(4) . . ? C13 C12 C11 118.8(4) . . ? C25 C24 C28 120.5(4) . . ? C25 C24 C23 119.0(4) . . ? C23 C24 C28 120.5(4) . . ? C12 C13 I13 119.1(3) . . ? C12 C13 C14 121.3(4) . . ? C14 C13 I13 119.6(4) . . ? C26 C25 C24 118.5(4) . . ? C2 C1 C7 118.3(4) . . ? C6 C1 C2 119.1(4) . . ? C6 C1 C7 122.6(4) . . ? N29 C28 C24 177.9(5) . . ? C3 C2 C1 119.5(4) . . ? C15 C16 C11 120.1(4) . . ? O2 C7 O1 125.4(4) 2_656 . ? O2 C7 C1 115.8(4) 2_656 . ? O1 C7 C1 118.7(4) . . ? O12 C17 O11 126.1(4) 2_656 . ? O12 C17 C11 116.6(4) 2_656 . ? O11 C17 C11 117.3(4) . . ? C2 C3 I3 117.9(4) . . ? C2 C3 C4 122.1(4) . . ? C4 C3 I3 120.0(4) . . ? C16 C15 C14 120.6(4) . . ? N21 C26 C25 122.8(4) . . ? N21 C22 C23 123.1(4) . . ? C1 C6 C5 120.7(5) . . ? C15 C14 C13 119.1(4) . . ? C3 C4 C5 119.2(5) . . ? C22 C23 C24 118.7(5) . . ? C4 C5 C6 119.4(5) . . ? data_ilb1199_0m _database_code_depnum_ccdc_archive 'CCDC 911304' #TrackingRef '5_nico.cif' _audit_creation_date 2011-06-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C30 H24 Cu2 I4 O10, 2(C H4 O)' _chemical_formula_sum 'C32 H32 Cu2 I4 O12' _chemical_formula_weight 1243.26 _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 monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 41.924(7) _cell_length_b 8.2952(14) _cell_length_c 22.541(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.592(3) _cell_angle_gamma 90.00 _cell_volume 7838(2) _cell_formula_units_Z 8 _cell_measurement_reflns_used 4892 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 27.95 _cell_measurement_theta_min 2.66 _exptl_absorpt_coefficient_mu 4.292 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.653468 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0889 before and 0.0391 after correction. The Ratio of minimum to maximum transmission is 0.653468. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour blue _exptl_crystal_colour_lustre ? _exptl_crystal_colour_modifier ? _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 2.107 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 4720 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_unetI/netI 0.0731 _diffrn_reflns_limit_h_max 59 _diffrn_reflns_limit_h_min -59 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 35460 _diffrn_reflns_theta_full 30.54 _diffrn_reflns_theta_max 30.54 _diffrn_reflns_theta_min 2.04 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _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' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_special_details ? _reflns_number_gt 7430 _reflns_number_total 11778 _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 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.293 _refine_diff_density_min -1.555 _refine_diff_density_rms 0.170 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 457 _refine_ls_number_reflns 11778 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0865 _refine_ls_R_factor_gt 0.0448 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0364P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0864 _refine_ls_wR_factor_ref 0.0991 _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. ; _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 I23 I 0.664189(8) -0.44575(4) 0.017889(15) 0.03400(9) Uani 1 1 d . . . I13 I 0.548258(10) 0.64243(4) 0.529948(16) 0.04468(11) Uani 1 1 d . . . Cu2 Cu 0.612782(12) 0.25175(5) 0.26701(2) 0.01582(11) Uani 1 1 d . . . I3 I 0.477049(8) -0.42069(4) 0.161095(16) 0.03467(9) Uani 1 1 d . . . Cu1 Cu 0.618471(12) -0.04796(5) 0.29711(2) 0.01520(11) Uani 1 1 d . . . O61 O 0.61360(7) 0.4960(3) 0.23427(12) 0.0181(6) Uani 1 1 d D . . H61 H 0.6319 0.5159 0.2227 0.027 Uiso 1 1 d RD . . O12 O 0.59398(7) 0.2809(3) 0.34560(13) 0.0213(7) Uani 1 1 d . . . O1 O 0.57566(7) -0.0667(3) 0.26173(13) 0.0209(6) Uani 1 1 d . . . O32 O 0.65484(7) 0.2812(3) 0.30496(13) 0.0219(7) Uani 1 1 d . . . O31 O 0.66182(7) 0.0190(3) 0.32478(13) 0.0208(7) Uani 1 1 d . . . O2 O 0.57164(7) 0.1909(3) 0.23330(14) 0.0240(7) Uani 1 1 d . . . O21 O 0.63525(7) -0.0865(3) 0.21692(13) 0.0230(7) Uani 1 1 d . . . O22 O 0.63264(7) 0.1755(3) 0.19299(13) 0.0218(7) Uani 1 1 d . . . O11 O 0.60175(7) 0.0236(3) 0.37382(12) 0.0193(6) Uani 1 1 d . . . O51 O 0.62700(9) -0.2905(3) 0.32103(13) 0.0321(8) Uani 1 1 d D . . H51 H 0.6195 -0.3658 0.2983 0.048 Uiso 1 1 d RD . . C21 C 0.64549(10) -0.0094(5) 0.11835(18) 0.0193(9) Uani 1 1 d . . . C31 C 0.70081(10) 0.2032(5) 0.35871(18) 0.0181(9) Uani 1 1 d . . . C27 C 0.63713(10) 0.0292(5) 0.18079(18) 0.0173(9) Uani 1 1 d . . . C7 C 0.56218(10) 0.0478(5) 0.23418(18) 0.0176(9) Uani 1 1 d . . . C32 C 0.71020(12) 0.3633(5) 0.3652(2) 0.0271(10) Uani 1 1 d . . . H32 H 0.6981 0.4476 0.3473 0.032 Uiso 1 1 calc R . . C12 C 0.57272(10) 0.3667(5) 0.45578(19) 0.0203(9) Uani 1 1 d . . . H12 H 0.5758 0.4489 0.4271 0.024 Uiso 1 1 calc R . . C22 C 0.65096(10) -0.1704(5) 0.10200(19) 0.0207(9) Uani 1 1 d . . . H22 H 0.6506 -0.2537 0.1309 0.025 Uiso 1 1 calc R . . C17 C 0.59319(10) 0.1668(5) 0.38300(18) 0.0181(9) Uani 1 1 d . . . C13 C 0.56039(12) 0.4033(5) 0.51069(19) 0.0246(10) Uani 1 1 d . . . C3 C 0.49531(11) -0.1844(5) 0.1615(2) 0.0225(10) Uani 1 1 d . . . C2 C 0.52224(11) -0.1506(5) 0.19516(19) 0.0207(9) Uani 1 1 d . . . H2 H 0.5332 -0.2343 0.2157 0.025 Uiso 1 1 calc R . . C11 C 0.58051(10) 0.2071(5) 0.44307(18) 0.0176(9) Uani 1 1 d . . . C23 C 0.65682(11) -0.2058(5) 0.0429(2) 0.0239(10) Uani 1 1 d . . . C37 C 0.67037(10) 0.1655(5) 0.32653(18) 0.0188(9) Uani 1 1 d . . . C61 C 0.59162(11) 0.5443(5) 0.1881(2) 0.0255(10) Uani 1 1 d D . . H61A H 0.5959 0.4824 0.1521 0.031 Uiso 1 1 calc R . . H61B H 0.5943 0.6596 0.1800 0.031 Uiso 1 1 calc R . . H61C H 0.5697 0.5240 0.2010 0.031 Uiso 1 1 calc R . . C16 C 0.57642(11) 0.0870(5) 0.48538(19) 0.0244(10) Uani 1 1 d . . . H16 H 0.5821 -0.0212 0.4768 0.029 Uiso 1 1 calc R . . C1 C 0.53310(10) 0.0085(5) 0.19846(18) 0.0192(9) Uani 1 1 d . . . C51 C 0.63227(14) -0.3521(5) 0.3788(2) 0.0342(12) Uani 1 1 d D . . H51A H 0.6530 -0.3149 0.3938 0.041 Uiso 1 1 calc R . . H51B H 0.6320 -0.4702 0.3776 0.041 Uiso 1 1 calc R . . H51C H 0.6154 -0.3139 0.4051 0.041 Uiso 1 1 calc R . . C25 C 0.65249(13) 0.0716(6) 0.0169(2) 0.0318(12) Uani 1 1 d . . . H25 H 0.6531 0.1544 -0.0122 0.038 Uiso 1 1 calc R . . C26 C 0.64614(12) 0.1122(5) 0.0754(2) 0.0278(11) Uani 1 1 d . . . H26 H 0.6423 0.2212 0.0861 0.033 Uiso 1 1 calc R . . C6 C 0.51686(11) 0.1282(5) 0.1674(2) 0.0253(10) Uani 1 1 d . . . H6 H 0.5241 0.2365 0.1698 0.030 Uiso 1 1 calc R . . C14 C 0.55595(12) 0.2854(6) 0.5533(2) 0.0279(11) Uani 1 1 d . . . H14 H 0.5476 0.3128 0.5910 0.034 Uiso 1 1 calc R . . C4 C 0.47904(11) -0.0656(6) 0.1300(2) 0.0278(11) Uani 1 1 d . . . H4 H 0.4606 -0.0915 0.1070 0.033 Uiso 1 1 calc R . . I33 I 0.751857(10) 0.63621(4) 0.41244(2) 0.05515(13) Uani 1 1 d . . . C34 C 0.75527(12) 0.2755(6) 0.4248(2) 0.0298(11) Uani 1 1 d . . . H34 H 0.7736 0.3001 0.4482 0.036 Uiso 1 1 calc R . . C33 C 0.73778(12) 0.3979(5) 0.3985(2) 0.0279(11) Uani 1 1 d . . . C24 C 0.65796(12) -0.0857(6) 0.0000(2) 0.0284(11) Uani 1 1 d . . . H24 H 0.6624 -0.1114 -0.0402 0.034 Uiso 1 1 calc R . . C5 C 0.49025(12) 0.0917(6) 0.1327(2) 0.0318(11) Uani 1 1 d . . . H5 H 0.4797 0.1744 0.1109 0.038 Uiso 1 1 calc R . . C36 C 0.71871(11) 0.0808(5) 0.3849(2) 0.0263(10) Uani 1 1 d . . . H36 H 0.7121 -0.0282 0.3807 0.032 Uiso 1 1 calc R . . C15 C 0.56387(12) 0.1270(5) 0.5404(2) 0.0302(11) Uani 1 1 d . . . H15 H 0.5607 0.0453 0.5693 0.036 Uiso 1 1 calc R . . C35 C 0.74593(12) 0.1168(6) 0.4168(2) 0.0316(11) Uani 1 1 d . . . H35 H 0.7584 0.0322 0.4335 0.038 Uiso 1 1 calc R . . O71 O 0.67204(8) 0.5450(4) 0.19893(17) 0.0385(9) Uani 1 1 d . . . H71 H 0.6793 0.6093 0.2245 0.046 Uiso 1 1 calc R . . O81 O 0.69971(10) 0.7571(5) 0.27307(18) 0.0490(10) Uani 1 1 d . . . H81 H 0.6868 0.8163 0.2912 0.059 Uiso 1 1 calc R . . C71 C 0.69487(12) 0.4225(6) 0.1880(2) 0.0377(13) Uani 1 1 d . . . H71A H 0.7153 0.4721 0.1774 0.045 Uiso 1 1 calc R . . H71B H 0.6874 0.3541 0.1553 0.045 Uiso 1 1 calc R . . H71C H 0.6977 0.3568 0.2238 0.045 Uiso 1 1 calc R . . C81 C 0.71988(16) 0.8524(8) 0.2391(3) 0.0609(19) Uani 1 1 d . . . H81A H 0.7078 0.8996 0.2060 0.073 Uiso 1 1 calc R . . H81B H 0.7372 0.7859 0.2236 0.073 Uiso 1 1 calc R . . H81C H 0.7288 0.9388 0.2638 0.073 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 I23 0.0417(2) 0.03128(17) 0.02904(18) -0.01338(14) -0.00001(14) 0.00262(15) I13 0.0766(3) 0.02415(16) 0.0336(2) -0.00658(15) 0.01505(19) 0.00911(17) Cu2 0.0209(3) 0.0115(2) 0.0151(2) -0.0002(2) -0.0020(2) -0.0006(2) I3 0.0371(2) 0.02303(15) 0.0437(2) -0.00882(15) -0.00945(16) -0.00551(14) Cu1 0.0199(3) 0.0116(2) 0.0140(2) -0.00015(19) -0.0011(2) 0.00048(19) O61 0.0220(16) 0.0126(13) 0.0196(15) -0.0007(12) -0.0045(12) -0.0019(12) O12 0.0292(18) 0.0166(14) 0.0181(15) -0.0009(12) 0.0043(13) 0.0021(12) O1 0.0246(17) 0.0179(14) 0.0202(16) 0.0023(13) -0.0054(13) -0.0024(12) O32 0.0228(17) 0.0185(14) 0.0243(17) 0.0008(13) -0.0081(13) -0.0020(12) O31 0.0218(17) 0.0160(14) 0.0244(17) -0.0002(13) -0.0033(13) 0.0017(12) O2 0.0252(18) 0.0180(14) 0.0288(18) -0.0003(13) -0.0063(14) -0.0028(13) O21 0.0346(19) 0.0177(14) 0.0170(15) 0.0009(12) 0.0057(14) 0.0026(13) O22 0.0323(19) 0.0144(13) 0.0189(16) -0.0005(12) 0.0028(13) 0.0032(13) O11 0.0258(17) 0.0169(14) 0.0153(15) -0.0019(12) 0.0021(12) -0.0001(12) O51 0.065(3) 0.0124(14) 0.0189(17) -0.0015(13) -0.0165(16) -0.0017(15) C21 0.020(2) 0.021(2) 0.016(2) -0.0017(18) -0.0012(17) 0.0006(18) C31 0.016(2) 0.023(2) 0.015(2) -0.0017(17) -0.0001(17) -0.0044(17) C27 0.018(2) 0.0191(19) 0.015(2) -0.0007(17) 0.0005(17) -0.0008(17) C7 0.019(2) 0.022(2) 0.012(2) -0.0025(18) 0.0027(16) -0.0032(17) C32 0.031(3) 0.025(2) 0.026(3) 0.002(2) -0.003(2) 0.002(2) C12 0.023(2) 0.018(2) 0.019(2) 0.0001(18) 0.0009(18) 0.0002(18) C22 0.024(2) 0.019(2) 0.019(2) 0.0018(18) -0.0015(18) -0.0012(18) C17 0.020(2) 0.0168(19) 0.017(2) 0.0017(17) -0.0013(17) -0.0028(17) C13 0.037(3) 0.021(2) 0.015(2) -0.0043(18) 0.005(2) 0.002(2) C3 0.028(3) 0.019(2) 0.021(2) -0.0044(18) 0.0011(19) -0.0034(19) C2 0.024(2) 0.019(2) 0.019(2) -0.0032(18) -0.0008(18) 0.0024(18) C11 0.022(2) 0.0149(18) 0.015(2) -0.0007(16) -0.0016(17) -0.0029(17) C23 0.023(3) 0.027(2) 0.021(2) -0.0082(19) -0.0016(19) 0.0012(19) C37 0.023(2) 0.022(2) 0.011(2) -0.0031(17) -0.0010(17) -0.0012(18) C61 0.025(3) 0.024(2) 0.027(3) 0.003(2) -0.008(2) 0.0022(19) C16 0.033(3) 0.023(2) 0.018(2) 0.0015(18) 0.0009(19) 0.0006(19) C1 0.018(2) 0.022(2) 0.017(2) -0.0032(18) 0.0020(17) -0.0032(18) C51 0.058(4) 0.024(2) 0.020(2) 0.002(2) -0.008(2) -0.003(2) C25 0.051(3) 0.027(2) 0.017(2) 0.006(2) 0.009(2) 0.000(2) C26 0.039(3) 0.021(2) 0.024(2) 0.0024(19) -0.003(2) 0.000(2) C6 0.026(3) 0.018(2) 0.032(3) 0.004(2) -0.001(2) -0.0008(19) C14 0.035(3) 0.030(2) 0.019(2) -0.002(2) 0.010(2) -0.003(2) C4 0.019(2) 0.032(3) 0.032(3) -0.004(2) -0.006(2) -0.002(2) I33 0.0588(3) 0.02743(17) 0.0785(3) -0.00053(19) -0.0348(2) -0.01148(17) C34 0.027(3) 0.032(2) 0.030(3) -0.007(2) -0.007(2) 0.001(2) C33 0.034(3) 0.021(2) 0.028(3) -0.001(2) -0.006(2) -0.006(2) C24 0.029(3) 0.038(3) 0.018(2) -0.003(2) 0.0013(19) -0.003(2) C5 0.029(3) 0.033(3) 0.033(3) 0.008(2) -0.003(2) 0.007(2) C36 0.027(3) 0.021(2) 0.031(3) -0.004(2) -0.007(2) 0.0007(19) C15 0.044(3) 0.023(2) 0.024(2) 0.000(2) 0.007(2) -0.008(2) C35 0.032(3) 0.031(2) 0.032(3) -0.002(2) -0.010(2) 0.009(2) O71 0.037(2) 0.036(2) 0.042(2) 0.0046(17) -0.0026(17) -0.0032(17) O81 0.041(3) 0.061(3) 0.045(2) -0.010(2) 0.0014(19) 0.016(2) C71 0.028(3) 0.040(3) 0.045(3) 0.009(3) 0.010(2) 0.001(2) C81 0.050(4) 0.072(5) 0.061(4) -0.022(4) 0.010(3) -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 I23 C23 2.093(4) . ? I13 C13 2.095(4) . ? Cu2 Cu1 2.5874(8) . ? Cu2 O61 2.157(3) . ? Cu2 O12 1.961(3) . ? Cu2 O32 1.967(3) . ? Cu2 O2 1.944(3) . ? Cu2 O22 1.976(3) . ? I3 C3 2.104(4) . ? Cu1 O1 1.963(3) . ? Cu1 O31 1.994(3) . ? Cu1 O21 1.972(3) . ? Cu1 O11 1.964(3) . ? Cu1 O51 2.113(3) . ? O61 C61 1.439(5) . ? O12 C17 1.269(5) . ? O1 C7 1.265(5) . ? O32 C37 1.255(5) . ? O31 C37 1.267(5) . ? O2 C7 1.252(5) . ? O21 C27 1.262(5) . ? O22 C27 1.259(5) . ? O11 C17 1.258(5) . ? O51 C51 1.415(5) . ? C21 C27 1.489(5) . ? C21 C22 1.405(6) . ? C21 C26 1.398(6) . ? C31 C32 1.392(6) . ? C31 C37 1.495(6) . ? C31 C36 1.390(6) . ? C7 C1 1.490(6) . ? C32 C33 1.402(7) . ? C12 C13 1.380(6) . ? C12 C11 1.394(5) . ? C22 C23 1.389(6) . ? C17 C11 1.498(6) . ? C13 C14 1.385(6) . ? C3 C2 1.383(6) . ? C3 C4 1.389(6) . ? C2 C1 1.398(6) . ? C11 C16 1.391(6) . ? C23 C24 1.389(6) . ? C16 C15 1.392(6) . ? C1 C6 1.389(6) . ? C25 C26 1.389(6) . ? C25 C24 1.380(6) . ? C6 C5 1.388(7) . ? C14 C15 1.387(6) . ? C4 C5 1.388(6) . ? I33 C33 2.086(4) . ? C34 C33 1.382(7) . ? C34 C35 1.385(6) . ? C36 C35 1.376(7) . ? O71 C71 1.419(6) . ? O81 C81 1.393(7) . ? 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 O61 Cu2 Cu1 172.15(8) . . ? O12 Cu2 Cu1 85.33(8) . . ? O12 Cu2 O61 101.60(11) . . ? O12 Cu2 O32 87.64(13) . . ? O12 Cu2 O22 168.16(12) . . ? O32 Cu2 Cu1 85.72(8) . . ? O32 Cu2 O61 90.85(11) . . ? O32 Cu2 O22 91.34(13) . . ? O2 Cu2 Cu1 86.09(9) . . ? O2 Cu2 O61 97.32(12) . . ? O2 Cu2 O12 91.26(13) . . ? O2 Cu2 O32 171.80(12) . . ? O2 Cu2 O22 88.07(13) . . ? O22 Cu2 Cu1 82.83(8) . . ? O22 Cu2 O61 90.20(11) . . ? O1 Cu1 Cu2 83.59(8) . . ? O1 Cu1 O31 167.37(12) . . ? O1 Cu1 O21 87.03(13) . . ? O1 Cu1 O11 92.78(12) . . ? O1 Cu1 O51 100.36(12) . . ? O31 Cu1 Cu2 84.01(8) . . ? O31 Cu1 O51 91.95(12) . . ? O21 Cu1 Cu2 87.03(8) . . ? O21 Cu1 O31 89.95(13) . . ? O21 Cu1 O51 91.06(12) . . ? O11 Cu1 Cu2 84.70(8) . . ? O11 Cu1 O31 88.45(12) . . ? O11 Cu1 O21 171.70(12) . . ? O11 Cu1 O51 97.13(12) . . ? O51 Cu1 Cu2 175.53(10) . . ? C61 O61 Cu2 119.8(2) . . ? C17 O12 Cu2 121.4(3) . . ? C7 O1 Cu1 122.8(3) . . ? C37 O32 Cu2 122.2(3) . . ? C37 O31 Cu1 122.2(3) . . ? C7 O2 Cu2 121.4(3) . . ? C27 O21 Cu1 119.6(3) . . ? C27 O22 Cu2 123.9(3) . . ? C17 O11 Cu1 122.3(3) . . ? C51 O51 Cu1 127.1(3) . . ? C22 C21 C27 119.6(4) . . ? C26 C21 C27 120.3(4) . . ? C26 C21 C22 120.0(4) . . ? C32 C31 C37 119.3(4) . . ? C36 C31 C32 120.1(4) . . ? C36 C31 C37 120.5(4) . . ? O21 C27 C21 117.6(4) . . ? O22 C27 O21 125.6(4) . . ? O22 C27 C21 116.8(4) . . ? O1 C7 C1 117.4(4) . . ? O2 C7 O1 125.4(4) . . ? O2 C7 C1 117.2(4) . . ? C31 C32 C33 118.8(4) . . ? C13 C12 C11 118.9(4) . . ? C23 C22 C21 118.9(4) . . ? O12 C17 C11 116.5(4) . . ? O11 C17 O12 125.9(4) . . ? O11 C17 C11 117.6(4) . . ? C12 C13 I13 119.2(3) . . ? C12 C13 C14 121.4(4) . . ? C14 C13 I13 119.3(3) . . ? C2 C3 I3 119.1(3) . . ? C2 C3 C4 122.1(4) . . ? C4 C3 I3 118.8(3) . . ? C3 C2 C1 118.9(4) . . ? C12 C11 C17 118.9(4) . . ? C16 C11 C12 120.6(4) . . ? C16 C11 C17 120.5(4) . . ? C22 C23 I23 119.1(3) . . ? C24 C23 I23 119.3(3) . . ? C24 C23 C22 121.6(4) . . ? O32 C37 O31 125.2(4) . . ? O32 C37 C31 117.7(4) . . ? O31 C37 C31 117.1(4) . . ? C11 C16 C15 119.4(4) . . ? C2 C1 C7 120.0(4) . . ? C6 C1 C7 120.7(4) . . ? C6 C1 C2 119.3(4) . . ? C24 C25 C26 121.7(4) . . ? C25 C26 C21 119.2(4) . . ? C5 C6 C1 121.0(4) . . ? C13 C14 C15 119.3(4) . . ? C5 C4 C3 118.6(4) . . ? C33 C34 C35 119.6(5) . . ? C32 C33 I33 120.4(3) . . ? C34 C33 C32 120.7(4) . . ? C34 C33 I33 118.9(4) . . ? C25 C24 C23 118.6(4) . . ? C6 C5 C4 120.0(4) . . ? C35 C36 C31 120.3(4) . . ? C14 C15 C16 120.4(4) . . ? C36 C35 C34 120.4(4) . . ? data_ilb1202_0m _database_code_depnum_ccdc_archive 'CCDC 911305' #TrackingRef '6_nico.cif' _audit_creation_date 2011-06-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C26 H20 Cu I2 N4 O6, C H2 Cl2' _chemical_formula_sum 'C27 H22 Cl2 Cu I2 N4 O6' _chemical_formula_weight 886.73 _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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 15 _space_group_name_H-M_alt 'C 1 2/c 1' _space_group_name_Hall '-C 2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.8470(9) _cell_length_b 14.0302(6) _cell_length_c 12.2535(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.970(2) _cell_angle_gamma 90.00 _cell_volume 3041.0(2) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8156 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 27.581 _cell_measurement_theta_min 2.904 _exptl_absorpt_coefficient_mu 2.972 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.744085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0831 before and 0.0286 after correction. The Ratio of minimum to maximum transmission is 0.744085. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour purple _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.937 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1716 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.12 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 17069 _diffrn_reflns_theta_full 27.67 _diffrn_reflns_theta_max 27.67 _diffrn_reflns_theta_min 1.85 _diffrn_ambient_temperature 120.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _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' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _reflns_number_gt 3191 _reflns_number_total 3535 _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 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.588 _refine_diff_density_min -1.424 _refine_diff_density_rms 0.119 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 3535 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0381 _refine_ls_R_factor_gt 0.0341 _refine_ls_restrained_S_all 1.089 _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^)+(0.0389P)^2^+20.6628P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0909 _refine_ls_wR_factor_ref 0.0932 _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. ; _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 0.7500 0.2500 0.5000 0.01508(13) Uani 1 2 d S . . I1 I 0.379670(15) 0.507175(19) 0.27547(2) 0.03068(10) Uani 1 1 d . . . C6 C 0.5159(2) 0.2521(3) 0.5604(4) 0.0298(8) Uani 1 1 d . . . H6 H 0.5415 0.2011 0.6142 0.036 Uiso 1 1 calc R . . O1 O 0.66147(15) 0.20620(18) 0.5864(2) 0.0224(5) Uani 1 1 d . . . O2 O 0.64447(14) 0.29798(17) 0.4297(2) 0.0190(5) Uani 1 1 d . . . C7 C 0.62198(19) 0.2630(2) 0.5031(3) 0.0183(7) Uani 1 1 d . . . N11 N 0.79789(18) 0.6989(2) 0.6599(3) 0.0226(6) Uani 1 1 d . . . H11A H 0.7884 0.7559 0.6262 0.027 Uiso 1 1 calc R . . H11B H 0.8183 0.6931 0.7400 0.027 Uiso 1 1 calc R . . N13 N 0.78411(16) 0.3579(2) 0.6167(3) 0.0176(6) Uani 1 1 d . . . O11 O 0.75265(16) 0.62558(18) 0.4764(2) 0.0238(5) Uani 1 1 d . . . C16 C 0.8312(2) 0.5112(3) 0.7770(3) 0.0211(7) Uani 1 1 d . . . H16 H 0.8475 0.5637 0.8319 0.025 Uiso 1 1 calc R . . C12 C 0.77389(19) 0.4473(2) 0.5744(3) 0.0169(6) Uani 1 1 d . . . H12 H 0.7499 0.4573 0.4884 0.020 Uiso 1 1 calc R . . C3 C 0.4401(2) 0.3993(3) 0.4012(3) 0.0253(8) Uani 1 1 d . . . C11 C 0.79675(19) 0.5257(2) 0.6508(3) 0.0169(6) Uani 1 1 d . . . C17 C 0.78145(19) 0.6216(2) 0.5898(3) 0.0176(6) Uani 1 1 d . . . C15 C 0.8413(2) 0.4180(3) 0.8208(3) 0.0220(7) Uani 1 1 d . . . H15 H 0.8641 0.4059 0.9064 0.026 Uiso 1 1 calc R . . C1 C 0.5461(2) 0.2930(3) 0.4888(3) 0.0212(7) Uani 1 1 d . . . C14 C 0.8177(2) 0.3436(3) 0.7387(3) 0.0209(7) Uani 1 1 d . . . H14 H 0.8255 0.2801 0.7690 0.025 Uiso 1 1 calc R . . C2 C 0.5076(2) 0.3671(3) 0.4079(3) 0.0213(7) Uani 1 1 d . . . H2 H 0.5276 0.3949 0.3581 0.026 Uiso 1 1 calc R . . C5 C 0.4479(2) 0.2861(4) 0.5529(4) 0.0383(10) Uani 1 1 d . . . H5 H 0.4273 0.2581 0.6018 0.046 Uiso 1 1 calc R . . C4 C 0.4102(2) 0.3608(4) 0.4744(4) 0.0342(9) Uani 1 1 d . . . H4 H 0.3646 0.3851 0.4708 0.041 Uiso 1 1 calc R . . Cl1 Cl 0.46984(8) 0.97451(14) 0.61714(13) 0.0615(4) Uani 1 1 d . . . C1S C 0.5000 0.9053(6) 0.7500 0.0524(19) Uani 1 2 d S . . H1SA H 0.4579 0.8637 0.7430 0.063 Uiso 0.50 1 calc PR . . H1SB H 0.5421 0.8637 0.7570 0.063 Uiso 0.50 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0187(3) 0.0102(3) 0.0142(3) -0.0004(2) 0.0055(2) 0.0007(2) I1 0.02658(15) 0.03175(16) 0.02502(15) -0.00607(10) 0.00409(11) 0.00932(10) C6 0.0280(19) 0.035(2) 0.029(2) 0.0039(17) 0.0147(17) -0.0028(16) O1 0.0282(13) 0.0192(12) 0.0186(12) 0.0058(10) 0.0096(10) 0.0030(10) O2 0.0218(12) 0.0183(12) 0.0166(12) 0.0034(9) 0.0085(10) 0.0027(10) C7 0.0220(16) 0.0146(15) 0.0159(15) -0.0028(13) 0.0065(13) -0.0021(13) N11 0.0352(17) 0.0133(14) 0.0174(14) -0.0015(11) 0.0102(13) -0.0017(12) N13 0.0211(14) 0.0139(13) 0.0157(13) 0.0004(11) 0.0064(11) 0.0002(11) O11 0.0388(15) 0.0152(12) 0.0164(12) 0.0010(10) 0.0116(11) 0.0014(11) C16 0.0255(18) 0.0186(17) 0.0194(17) -0.0054(13) 0.0102(15) -0.0029(14) C12 0.0209(15) 0.0146(15) 0.0137(15) 0.0012(12) 0.0065(13) 0.0014(13) C3 0.0211(17) 0.030(2) 0.0182(17) -0.0054(15) 0.0028(14) 0.0022(15) C11 0.0201(16) 0.0135(15) 0.0180(16) 0.0004(13) 0.0093(13) 0.0003(13) C17 0.0221(16) 0.0130(15) 0.0195(16) -0.0007(13) 0.0110(13) -0.0003(12) C15 0.0277(18) 0.0207(17) 0.0148(16) 0.0007(13) 0.0071(14) 0.0010(14) C1 0.0208(16) 0.0222(18) 0.0181(16) -0.0042(14) 0.0065(13) -0.0036(14) C14 0.0257(17) 0.0152(16) 0.0210(17) 0.0025(13) 0.0098(14) 0.0004(13) C2 0.0221(17) 0.0224(17) 0.0166(16) -0.0045(14) 0.0064(13) -0.0015(14) C5 0.031(2) 0.055(3) 0.033(2) 0.002(2) 0.0184(18) -0.008(2) C4 0.0208(18) 0.050(3) 0.032(2) -0.0060(19) 0.0122(16) -0.0010(17) Cl1 0.0378(6) 0.1029(12) 0.0379(7) 0.0057(7) 0.0120(5) 0.0088(7) C1S 0.044(4) 0.067(5) 0.056(5) 0.000 0.031(4) 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 O2 1.986(2) 7_656 ? Cu1 O2 1.986(2) . ? Cu1 N13 1.979(3) . ? Cu1 N13 1.979(3) 7_656 ? I1 C3 2.104(4) . ? C6 C1 1.391(5) . ? C6 C5 1.394(6) . ? O1 C7 1.251(4) . ? O2 C7 1.270(4) . ? C7 C1 1.496(5) . ? N11 C17 1.329(4) . ? N13 C12 1.338(4) . ? N13 C14 1.348(4) . ? O11 C17 1.242(4) . ? C16 C11 1.393(5) . ? C16 C15 1.393(5) . ? C12 C11 1.381(5) . ? C3 C2 1.380(5) . ? C3 C4 1.391(6) . ? C11 C17 1.502(5) . ? C15 C14 1.376(5) . ? C1 C2 1.400(5) . ? C5 C4 1.389(7) . ? Cl1 C1S 1.752(5) . ? C1S Cl1 1.752(5) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Cu1 O2 180.00(13) . 7_656 ? N13 Cu1 O2 89.88(11) . 7_656 ? N13 Cu1 O2 90.12(11) 7_656 7_656 ? N13 Cu1 O2 89.88(11) 7_656 . ? N13 Cu1 O2 90.12(11) . . ? N13 Cu1 N13 179.999(1) . 7_656 ? C1 C6 C5 119.9(4) . . ? C7 O2 Cu1 101.7(2) . . ? O1 C7 O2 122.2(3) . . ? O1 C7 C1 120.0(3) . . ? O2 C7 C1 117.8(3) . . ? C12 N13 Cu1 119.7(2) . . ? C12 N13 C14 118.8(3) . . ? C14 N13 Cu1 121.5(2) . . ? C11 C16 C15 118.5(3) . . ? N13 C12 C11 122.6(3) . . ? C2 C3 I1 119.6(3) . . ? C2 C3 C4 121.4(4) . . ? C4 C3 I1 118.9(3) . . ? C16 C11 C17 124.8(3) . . ? C12 C11 C16 118.7(3) . . ? C12 C11 C17 116.5(3) . . ? N11 C17 C11 118.3(3) . . ? O11 C17 N11 122.7(3) . . ? O11 C17 C11 118.9(3) . . ? C14 C15 C16 119.2(3) . . ? C6 C1 C7 120.6(3) . . ? C6 C1 C2 120.0(3) . . ? C2 C1 C7 119.3(3) . . ? N13 C14 C15 122.1(3) . . ? C3 C2 C1 119.3(3) . . ? C4 C5 C6 120.3(4) . . ? C5 C4 C3 119.1(4) . . ? Cl1 C1S Cl1 112.6(5) 2_656 . ? data_ilb1403_0m _database_code_depnum_ccdc_archive 'CCDC 911306' #TrackingRef '7_MeOH.cif' _audit_creation_date 2011-06-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C40 H28 Cu2 I4 N4 O10' _chemical_formula_sum 'C40 H28 Cu2 I4 N4 O10' _chemical_formula_weight 1359.34 _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' N N 0.0061 0.0033 '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' Cu Cu 0.3201 1.2651 '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 14.5424(3) _cell_length_b 16.5333(4) _cell_length_c 18.3008(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.6760(10) _cell_angle_gamma 90.00 _cell_volume 4349.78(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9990 _cell_measurement_temperature 100.0 _cell_measurement_theta_max 28.09 _cell_measurement_theta_min 2.46 _exptl_absorpt_coefficient_mu 3.877 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_correction_T_min 0.701568 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2004/1 (Bruker,2004) was used for absorption correction. R(int) was 0.0572 before and 0.0248 after correction. The Ratio of minimum to maximum transmission is 0.701568. The \l/2 correction factor is 0.0015 ; _exptl_crystal_colour 'clear greenish blue' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier greenish _exptl_crystal_colour_primary blue _exptl_crystal_density_diffrn 2.076 _exptl_crystal_density_meas 0 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2584 _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.4 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0257 _diffrn_reflns_av_unetI/netI 0.0334 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 21777 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.25 _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _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 7458 _reflns_number_total 8822 _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 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'smtbx-flip (Bourhis, 2008)' _refine_diff_density_max 2.248 _refine_diff_density_min -1.717 _refine_diff_density_rms 0.135 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 541 _refine_ls_number_reflns 8822 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0367 _refine_ls_restrained_S_all 1.053 _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^)+(0.0343P)^2^+16.5106P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0853 _refine_ls_wR_factor_ref 0.0903 _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. ; _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 I33 I -0.03678(2) 0.60273(2) 0.703952(17) 0.02835(9) Uani 1 1 d . . . I3 I 0.21133(3) 0.99194(2) 0.249963(18) 0.03684(10) Uani 1 1 d . . . I13 I 0.87993(3) 0.98182(3) 0.52321(2) 0.04720(12) Uani 1 1 d . . . Cu2 Cu 0.42436(3) 0.87499(3) 0.61607(2) 0.01173(11) Uani 1 1 d . . . Cu1 Cu 0.42643(3) 0.71336(3) 0.61528(2) 0.01269(11) Uani 1 1 d . . . O32 O 0.3018(2) 0.85325(18) 0.64812(18) 0.0238(7) Uani 1 1 d . . . O1 O 0.3799(2) 0.72581(18) 0.50723(15) 0.0200(6) Uani 1 1 d . . . O21 O 0.4694(2) 0.73474(17) 0.72270(15) 0.0171(6) Uani 1 1 d . . . O2 O 0.3680(2) 0.86037(18) 0.51332(15) 0.0216(7) Uani 1 1 d . . . O11 O 0.5543(2) 0.72779(18) 0.59611(16) 0.0205(6) Uani 1 1 d . . . O12 O 0.5495(2) 0.86261(19) 0.58862(17) 0.0235(7) Uani 1 1 d . . . O31 O 0.2971(2) 0.71897(17) 0.63444(15) 0.0168(6) Uani 1 1 d . . . O48 O 0.2564(2) 0.34454(19) 0.62118(18) 0.0279(7) Uani 1 1 d . . . O22 O 0.4809(2) 0.86962(18) 0.72053(16) 0.0253(7) Uani 1 1 d . . . N59 N 0.1834(3) 1.1997(2) 0.67759(19) 0.0187(7) Uani 1 1 d . . . H59A H 0.1335 1.2097 0.6980 0.022 Uiso 1 1 calc R . . H59B H 0.2093 1.2386 0.6550 0.022 Uiso 1 1 calc R . . N49 N 0.2248(3) 0.4467(2) 0.6956(2) 0.0258(9) Uani 1 1 d . . . H49A H 0.1745 0.4227 0.7064 0.031 Uiso 1 1 calc R . . H49B H 0.2414 0.4942 0.7149 0.031 Uiso 1 1 calc R . . N51 N 0.4044(2) 1.0059(2) 0.61151(18) 0.0150(7) Uani 1 1 d . . . C17 C 0.5888(3) 0.7954(3) 0.5854(2) 0.0161(8) Uani 1 1 d . . . C27 C 0.4918(3) 0.8025(3) 0.7519(2) 0.0163(8) Uani 1 1 d . B . C21 C 0.5353(3) 0.8019(3) 0.8324(2) 0.0205(9) Uani 1 1 d . . . C3 C 0.2453(3) 0.8778(3) 0.2967(2) 0.0207(9) Uani 1 1 d . . . N41 N 0.4343(3) 0.5827(2) 0.61668(17) 0.0167(7) Uani 1 1 d . . . C12 C 0.7279(3) 0.8703(3) 0.5590(2) 0.0228(9) Uani 1 1 d . . . H12 H 0.6968 0.9193 0.5670 0.027 Uiso 1 1 calc R . . C33 C 0.0306(3) 0.7128(3) 0.6928(2) 0.0192(9) Uani 1 1 d . . . C57 C 0.2195(3) 1.1259(3) 0.6809(2) 0.0175(9) Uani 1 1 d . . . C11 C 0.6858(3) 0.7966(3) 0.5673(2) 0.0183(9) Uani 1 1 d . . . C6 C 0.2929(3) 0.7283(3) 0.3581(2) 0.0206(9) Uani 1 1 d . . . H6 H 0.3095 0.6768 0.3792 0.025 Uiso 1 1 calc R . . C31 C 0.1646(3) 0.7856(3) 0.6663(2) 0.0150(8) Uani 1 1 d . . . C7 C 0.3567(3) 0.7936(3) 0.4797(2) 0.0146(8) Uani 1 1 d . . . C13 C 0.8163(3) 0.8719(3) 0.5387(2) 0.0256(10) Uani 1 1 d . . . C35 C 0.0277(3) 0.8575(3) 0.6912(2) 0.0249(10) Uani 1 1 d . . . H35 H -0.0041 0.9069 0.6961 0.030 Uiso 1 1 calc R . . C47 C 0.2757(3) 0.4111(3) 0.6502(2) 0.0205(9) Uani 1 1 d . . . C46 C 0.5053(3) 0.5415(3) 0.5960(2) 0.0213(9) Uani 1 1 d . . . H46 H 0.5575 0.5709 0.5845 0.026 Uiso 1 1 calc R . . C37 C 0.2621(3) 0.7857(2) 0.6482(2) 0.0144(8) Uani 1 1 d . . . C43 C 0.3581(3) 0.4564(2) 0.6323(2) 0.0185(9) Uani 1 1 d . . . C36 C 0.1180(3) 0.8582(3) 0.6737(2) 0.0199(9) Uani 1 1 d . . . H36 H 0.1476 0.9083 0.6669 0.024 Uiso 1 1 calc R . . C1 C 0.3122(3) 0.7980(3) 0.4001(2) 0.0153(8) Uani 1 1 d . . . C16 C 0.7316(3) 0.7247(3) 0.5555(2) 0.0217(9) Uani 1 1 d . . . H16 H 0.7022 0.6742 0.5611 0.026 Uiso 1 1 calc R . . C26 C 0.5517(3) 0.7294(3) 0.8700(2) 0.0215(9) Uani 1 1 d . B . H26 H 0.5335 0.6797 0.8460 0.026 Uiso 1 1 calc R . . C2 C 0.2878(3) 0.8734(3) 0.3693(2) 0.0171(8) Uani 1 1 d . . . H2 H 0.3003 0.9212 0.3978 0.021 Uiso 1 1 calc R . . C5 C 0.2494(3) 0.7339(3) 0.2855(2) 0.0228(9) Uani 1 1 d . . . H5 H 0.2367 0.6862 0.2569 0.027 Uiso 1 1 calc R . . C32 C 0.1205(3) 0.7123(3) 0.6760(2) 0.0185(9) Uani 1 1 d . . . H32 H 0.1518 0.6626 0.6712 0.022 Uiso 1 1 calc R . . C34 C -0.0150(3) 0.7849(3) 0.7011(2) 0.0258(10) Uani 1 1 d . . . H34 H -0.0760 0.7843 0.7137 0.031 Uiso 1 1 calc R . . C54 C 0.3628(3) 1.1695(2) 0.6240(2) 0.0181(9) Uani 1 1 d . . . H54 H 0.3488 1.2253 0.6281 0.022 Uiso 1 1 calc R . . C42 C 0.3631(3) 0.5405(3) 0.6347(2) 0.0182(9) Uani 1 1 d . . . H42 H 0.3128 0.5693 0.6500 0.022 Uiso 1 1 calc R . . C52 C 0.3287(3) 1.0307(2) 0.6383(2) 0.0156(8) Uani 1 1 d . . . H52 H 0.2884 0.9905 0.6529 0.019 Uiso 1 1 calc R . . C4 C 0.2241(3) 0.8088(3) 0.2542(2) 0.0233(10) Uani 1 1 d . . . H4 H 0.1930 0.8127 0.2048 0.028 Uiso 1 1 calc R . . C55 C 0.4416(3) 1.1448(3) 0.5955(2) 0.0193(9) Uani 1 1 d . . . H55 H 0.4825 1.1838 0.5799 0.023 Uiso 1 1 calc R . . C25 C 0.5949(3) 0.7297(3) 0.9431(2) 0.0270(10) Uani 1 1 d . . . H25 H 0.6060 0.6801 0.9691 0.032 Uiso 1 1 calc R B . C53 C 0.3049(3) 1.1103(2) 0.6463(2) 0.0148(8) Uani 1 1 d . . . C14 C 0.8620(3) 0.8002(4) 0.5268(3) 0.0339(12) Uani 1 1 d . . . H14 H 0.9222 0.8019 0.5125 0.041 Uiso 1 1 calc R . . C24 C 0.6222(4) 0.8021(3) 0.9786(3) 0.0364(13) Uani 1 1 d . B . H24 H 0.6626 0.8031 1.0245 0.044 Uiso 1 1 calc R A 1 C15 C 0.8202(3) 0.7267(3) 0.5357(3) 0.0302(11) Uani 1 1 d . . . H15 H 0.8517 0.6777 0.5284 0.036 Uiso 1 1 calc R . . C45 C 0.5061(3) 0.4584(3) 0.5906(3) 0.0282(10) Uani 1 1 d . . . H45 H 0.5570 0.4312 0.5745 0.034 Uiso 1 1 calc R . . C56 C 0.4601(3) 1.0638(3) 0.5902(2) 0.0169(8) Uani 1 1 d . . . H56 H 0.5144 1.0479 0.5708 0.020 Uiso 1 1 calc R . . C22A C 0.5470(7) 0.8723(6) 0.8720(5) 0.0221(14) Uiso 0.4987(9) 1 d P B 1 H22 H 0.5268 0.9223 0.8497 0.026 Uiso 0.4987(9) 1 calc PR B 1 C44 C 0.4315(3) 0.4151(3) 0.6088(2) 0.0243(10) Uani 1 1 d . . . H44 H 0.4304 0.3577 0.6054 0.029 Uiso 1 1 calc R . . C23A C 0.5890(7) 0.8695(6) 0.9454(5) 0.0233(14) Uiso 0.4987(9) 1 d P B 1 I23A I 0.61795(9) 0.97707(6) 1.00528(5) 0.0618(2) Uani 0.4987(9) 1 d P B 1 O58 O 0.1846(2) 1.06990(18) 0.71227(17) 0.0242(7) Uani 1 1 d . . . I23B I 0.68081(9) 0.98345(5) 0.98050(5) 0.0618(2) Uani 0.5013(9) 1 d P B 2 C23B C 0.6203(7) 0.8765(6) 0.9343(5) 0.0233(14) Uiso 0.5013(9) 1 d P B 2 C22B C 0.5741(7) 0.8754(6) 0.8629(5) 0.0221(14) Uiso 0.5013(9) 1 d P B 2 H22A H 0.5682 0.9235 0.8343 0.026 Uiso 0.5013(9) 1 calc PR B 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 I33 0.02281(16) 0.03249(18) 0.03011(16) 0.00174(13) 0.00512(12) -0.01201(13) I3 0.0494(2) 0.02838(18) 0.02860(16) 0.00891(13) -0.00754(15) 0.00530(15) I13 0.0274(2) 0.0575(3) 0.0580(2) 0.01257(19) 0.01088(17) -0.02004(18) Cu2 0.0118(2) 0.0120(2) 0.0118(2) -0.00041(17) 0.00311(18) -0.00010(18) Cu1 0.0128(2) 0.0118(2) 0.0138(2) 0.00045(17) 0.00321(18) -0.00018(18) O32 0.0190(17) 0.0148(15) 0.0416(18) -0.0049(13) 0.0177(14) -0.0036(12) O1 0.0246(17) 0.0193(16) 0.0152(13) 0.0002(11) 0.0005(12) 0.0010(13) O21 0.0180(16) 0.0164(15) 0.0162(13) -0.0004(11) 0.0002(11) -0.0004(12) O2 0.0264(18) 0.0181(16) 0.0181(14) -0.0008(12) -0.0042(13) 0.0022(13) O11 0.0185(16) 0.0194(16) 0.0248(15) 0.0029(12) 0.0076(13) 0.0015(13) O12 0.0146(16) 0.0238(17) 0.0338(17) 0.0022(13) 0.0089(13) 0.0013(13) O31 0.0142(15) 0.0131(14) 0.0240(15) -0.0024(11) 0.0053(12) -0.0016(11) O48 0.037(2) 0.0148(16) 0.0314(17) -0.0035(13) 0.0053(15) -0.0069(14) O22 0.041(2) 0.0155(15) 0.0163(14) 0.0015(12) -0.0041(13) -0.0023(14) N59 0.0183(19) 0.0147(18) 0.0247(18) -0.0001(14) 0.0081(15) 0.0011(14) N49 0.036(2) 0.0155(19) 0.0283(19) 0.0010(15) 0.0112(17) -0.0074(17) N51 0.0134(18) 0.0178(18) 0.0144(15) -0.0012(13) 0.0041(13) -0.0008(14) C17 0.013(2) 0.023(2) 0.0120(17) 0.0001(16) 0.0011(15) 0.0016(17) C27 0.014(2) 0.021(2) 0.0139(18) 0.0014(16) 0.0021(16) -0.0012(17) C21 0.022(2) 0.025(2) 0.0130(18) 0.0004(17) -0.0009(17) 0.0017(18) C3 0.019(2) 0.023(2) 0.020(2) 0.0026(17) 0.0019(17) 0.0027(18) N41 0.022(2) 0.0147(17) 0.0134(15) -0.0012(13) 0.0016(14) 0.0022(14) C12 0.017(2) 0.029(2) 0.023(2) 0.0000(18) 0.0037(18) 0.0004(19) C33 0.015(2) 0.028(2) 0.0141(18) 0.0008(16) 0.0014(16) -0.0067(18) C57 0.017(2) 0.019(2) 0.0175(19) -0.0021(16) 0.0053(16) 0.0000(17) C11 0.012(2) 0.028(2) 0.0141(18) 0.0001(16) 0.0011(16) 0.0000(18) C6 0.019(2) 0.022(2) 0.021(2) -0.0018(17) 0.0034(17) 0.0010(18) C31 0.009(2) 0.024(2) 0.0122(17) 0.0000(15) 0.0005(15) -0.0025(16) C7 0.0077(19) 0.021(2) 0.0154(18) -0.0005(16) 0.0034(15) 0.0004(16) C13 0.014(2) 0.040(3) 0.022(2) 0.0037(19) 0.0026(18) -0.009(2) C35 0.016(2) 0.030(3) 0.029(2) -0.0061(19) 0.0058(19) 0.0028(19) C47 0.027(2) 0.015(2) 0.0182(19) 0.0049(16) -0.0005(18) -0.0015(18) C46 0.019(2) 0.019(2) 0.025(2) -0.0019(17) 0.0025(18) 0.0035(18) C37 0.015(2) 0.017(2) 0.0117(17) 0.0012(15) 0.0017(15) 0.0022(16) C43 0.027(2) 0.012(2) 0.0153(18) -0.0001(15) -0.0002(17) 0.0006(17) C36 0.016(2) 0.022(2) 0.022(2) -0.0029(17) 0.0048(17) -0.0023(17) C1 0.0075(19) 0.023(2) 0.0160(18) 0.0008(16) 0.0023(15) 0.0020(16) C16 0.015(2) 0.031(3) 0.019(2) -0.0015(18) 0.0007(17) 0.0010(18) C26 0.014(2) 0.028(2) 0.023(2) 0.0034(18) 0.0035(17) 0.0000(18) C2 0.014(2) 0.019(2) 0.0182(19) -0.0030(16) 0.0008(16) 0.0009(16) C5 0.020(2) 0.029(2) 0.018(2) -0.0057(18) 0.0002(17) -0.0034(19) C32 0.015(2) 0.025(2) 0.0150(18) -0.0010(16) 0.0001(16) -0.0010(17) C34 0.017(2) 0.036(3) 0.025(2) -0.0042(19) 0.0055(18) 0.000(2) C54 0.024(2) 0.0112(19) 0.021(2) 0.0030(16) 0.0064(17) -0.0006(17) C42 0.022(2) 0.016(2) 0.0173(19) 0.0000(16) 0.0042(17) 0.0021(17) C52 0.017(2) 0.015(2) 0.0168(18) 0.0017(15) 0.0062(16) -0.0008(16) C4 0.017(2) 0.035(3) 0.0166(19) -0.0011(18) -0.0009(17) 0.0004(19) C55 0.021(2) 0.016(2) 0.021(2) 0.0015(16) 0.0060(17) -0.0038(17) C25 0.020(2) 0.039(3) 0.022(2) 0.009(2) 0.0013(18) 0.004(2) C53 0.017(2) 0.016(2) 0.0129(17) -0.0011(15) 0.0050(16) -0.0013(16) C14 0.014(2) 0.063(4) 0.026(2) -0.006(2) 0.0072(19) -0.003(2) C24 0.043(3) 0.046(3) 0.016(2) -0.003(2) -0.007(2) 0.017(3) C15 0.023(3) 0.042(3) 0.025(2) -0.006(2) 0.0053(19) 0.011(2) C45 0.024(3) 0.027(3) 0.034(2) 0.000(2) 0.007(2) 0.010(2) C56 0.016(2) 0.020(2) 0.0150(18) 0.0002(16) 0.0048(16) -0.0008(17) C44 0.032(3) 0.012(2) 0.028(2) -0.0001(17) 0.000(2) 0.0030(19) I23A 0.0986(7) 0.0366(3) 0.0363(4) -0.0107(3) -0.0347(4) 0.0000(4) O58 0.0259(18) 0.0187(16) 0.0326(16) 0.0065(13) 0.0197(14) 0.0035(13) I23B 0.0986(7) 0.0366(3) 0.0363(4) -0.0107(3) -0.0347(4) 0.0000(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 I33 C33 2.092(4) . ? I3 C3 2.099(4) . ? I13 C13 2.078(5) . ? Cu2 Cu1 2.6725(7) . ? Cu2 O32 1.991(3) . ? Cu2 O2 1.950(3) . ? Cu2 O12 1.971(3) . ? Cu2 O22 1.966(3) . ? Cu2 N51 2.183(3) . ? Cu1 O1 2.002(3) . ? Cu1 O21 2.002(3) . ? Cu1 O11 1.958(3) . ? Cu1 O31 1.966(3) . ? Cu1 N41 2.163(4) . ? O32 C37 1.257(5) . ? O1 C7 1.254(5) . ? O21 C27 1.262(5) . ? O2 C7 1.262(5) . ? O11 C17 1.252(5) . ? O12 C17 1.255(5) . ? O31 C37 1.257(5) . ? O48 C47 1.235(5) . ? O22 C27 1.249(5) . ? N59 C57 1.326(5) . ? N49 C47 1.331(6) . ? N51 C52 1.337(5) . ? N51 C56 1.349(5) . ? C17 C11 1.497(6) . ? C27 C21 1.515(5) . ? C21 C26 1.385(6) . ? C21 C22A 1.368(11) . ? C21 C22B 1.418(11) . ? C3 C2 1.381(6) . ? C3 C4 1.388(6) . ? N41 C46 1.339(5) . ? N41 C42 1.330(5) . ? C12 C11 1.381(6) . ? C12 C13 1.392(6) . ? C33 C32 1.388(6) . ? C33 C34 1.383(7) . ? C57 C53 1.499(5) . ? C57 O58 1.239(5) . ? C11 C16 1.396(6) . ? C6 C1 1.391(6) . ? C6 C5 1.385(6) . ? C31 C37 1.504(6) . ? C31 C36 1.396(6) . ? C31 C32 1.394(6) . ? C7 C1 1.504(5) . ? C13 C14 1.391(8) . ? C35 C36 1.397(6) . ? C35 C34 1.376(7) . ? C47 C43 1.492(6) . ? C46 C45 1.378(7) . ? C43 C42 1.392(6) . ? C43 C44 1.388(6) . ? C1 C2 1.393(6) . ? C16 C15 1.390(6) . ? C26 C25 1.390(6) . ? C5 C4 1.391(7) . ? C54 C55 1.390(6) . ? C54 C53 1.391(6) . ? C52 C53 1.374(6) . ? C55 C56 1.372(6) . ? C25 C24 1.390(7) . ? C14 C15 1.380(8) . ? C24 C23A 1.325(11) . ? C24 C23B 1.472(11) . ? C45 C44 1.382(7) . ? C22A C23A 1.390(14) . ? C23A I23A 2.098(10) . ? I23B C23B 2.095(10) . ? C23B C22B 1.376(14) . ? 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 O32 Cu2 Cu1 80.35(9) . . ? O32 Cu2 N51 94.06(12) . . ? O2 Cu2 Cu1 82.78(9) . . ? O2 Cu2 O32 89.81(14) . . ? O2 Cu2 O12 90.66(13) . . ? O2 Cu2 O22 170.29(13) . . ? O2 Cu2 N51 92.98(12) . . ? O12 Cu2 Cu1 83.29(9) . . ? O12 Cu2 O32 163.44(13) . . ? O12 Cu2 N51 102.44(13) . . ? O22 Cu2 Cu1 87.52(9) . . ? O22 Cu2 O32 88.13(14) . . ? O22 Cu2 O12 88.63(14) . . ? O22 Cu2 N51 96.64(12) . . ? N51 Cu2 Cu1 172.95(10) . . ? O1 Cu1 Cu2 84.27(9) . . ? O1 Cu1 O21 163.87(12) . . ? O1 Cu1 N41 97.11(12) . . ? O21 Cu1 Cu2 79.65(8) . . ? O21 Cu1 N41 99.01(12) . . ? O11 Cu1 Cu2 83.73(9) . . ? O11 Cu1 O1 89.94(12) . . ? O11 Cu1 O21 89.45(12) . . ? O11 Cu1 O31 170.29(12) . . ? O11 Cu1 N41 94.24(13) . . ? O31 Cu1 Cu2 86.56(8) . . ? O31 Cu1 O1 88.94(12) . . ? O31 Cu1 O21 88.95(12) . . ? O31 Cu1 N41 95.47(13) . . ? N41 Cu1 Cu2 177.56(10) . . ? C37 O32 Cu2 126.3(3) . . ? C7 O1 Cu1 121.2(3) . . ? C27 O21 Cu1 126.5(3) . . ? C7 O2 Cu2 125.7(3) . . ? C17 O11 Cu1 123.4(3) . . ? C17 O12 Cu2 123.2(3) . . ? C37 O31 Cu1 120.3(3) . . ? C27 O22 Cu2 119.5(3) . . ? C52 N51 Cu2 113.7(3) . . ? C52 N51 C56 116.8(4) . . ? C56 N51 Cu2 129.3(3) . . ? O11 C17 O12 126.0(4) . . ? O11 C17 C11 117.4(4) . . ? O12 C17 C11 116.6(4) . . ? O21 C27 C21 116.7(4) . . ? O22 C27 O21 126.0(4) . . ? O22 C27 C21 117.3(4) . . ? C26 C21 C27 120.3(4) . . ? C26 C21 C22B 121.2(5) . . ? C22A C21 C27 120.7(6) . . ? C22A C21 C26 118.4(6) . . ? C22A C21 C22B 18.6(5) . . ? C22B C21 C27 117.4(5) . . ? C2 C3 I3 118.9(3) . . ? C2 C3 C4 121.7(4) . . ? C4 C3 I3 119.5(3) . . ? C46 N41 Cu1 123.1(3) . . ? C42 N41 Cu1 119.0(3) . . ? C42 N41 C46 117.7(4) . . ? C11 C12 C13 119.3(4) . . ? C32 C33 I33 119.2(3) . . ? C34 C33 I33 120.0(3) . . ? C34 C33 C32 120.8(4) . . ? N59 C57 C53 119.2(4) . . ? O58 C57 N59 121.4(4) . . ? O58 C57 C53 119.4(4) . . ? C12 C11 C17 119.0(4) . . ? C12 C11 C16 120.3(4) . . ? C16 C11 C17 120.7(4) . . ? C5 C6 C1 120.0(4) . . ? C36 C31 C37 120.6(4) . . ? C32 C31 C37 119.7(4) . . ? C32 C31 C36 119.7(4) . . ? O1 C7 O2 125.4(4) . . ? O1 C7 C1 118.8(4) . . ? O2 C7 C1 115.8(4) . . ? C12 C13 I13 120.1(4) . . ? C14 C13 I13 119.4(3) . . ? C14 C13 C12 120.5(5) . . ? C34 C35 C36 119.8(4) . . ? O48 C47 N49 123.5(4) . . ? O48 C47 C43 119.4(4) . . ? N49 C47 C43 117.1(4) . . ? N41 C46 C45 122.8(4) . . ? O32 C37 O31 125.4(4) . . ? O32 C37 C31 116.8(4) . . ? O31 C37 C31 117.8(4) . . ? C42 C43 C47 122.3(4) . . ? C44 C43 C47 120.1(4) . . ? C44 C43 C42 117.5(4) . . ? C31 C36 C35 120.1(4) . . ? C6 C1 C7 121.2(4) . . ? C6 C1 C2 120.0(4) . . ? C2 C1 C7 118.8(4) . . ? C15 C16 C11 120.2(4) . . ? C21 C26 C25 119.5(4) . . ? C3 C2 C1 119.2(4) . . ? C6 C5 C4 120.6(4) . . ? C33 C32 C31 119.3(4) . . ? C35 C34 C33 120.2(4) . . ? C55 C54 C53 118.2(4) . . ? N41 C42 C43 123.7(4) . . ? N51 C52 C53 124.6(4) . . ? C3 C4 C5 118.6(4) . . ? C56 C55 C54 119.7(4) . . ? C26 C25 C24 120.6(4) . . ? C54 C53 C57 125.4(4) . . ? C52 C53 C57 116.5(4) . . ? C52 C53 C54 118.0(4) . . ? C15 C14 C13 120.1(4) . . ? C25 C24 C23B 118.8(5) . . ? C23A C24 C25 116.8(6) . . ? C23A C24 C23B 21.4(5) . . ? C14 C15 C16 119.6(5) . . ? C46 C45 C44 119.0(4) . . ? N51 C56 C55 122.7(4) . . ? C21 C22A C23A 119.0(9) . . ? C45 C44 C43 119.2(4) . . ? C24 C23A C22A 123.2(9) . . ? C24 C23A I23A 116.3(6) . . ? C22A C23A I23A 120.1(7) . . ? C24 C23B I23B 120.8(6) . . ? C22B C23B C24 118.5(8) . . ? C22B C23B I23B 120.7(7) . . ? C23B C22B C21 119.6(9) . . ?