# Electronic Supplementary Material (ESI) for Chemical Communications # 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_global data_1-100K #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_update_record ; 2013-01-11 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 Cu2 I2 N4' _chemical_formula_weight 585.16 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pnn2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 17.6379(5) _cell_length_b 9.6123(5) _cell_length_c 9.8809(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1675.22(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5938 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 27.43 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 6.216 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3056 _exptl_absorpt_correction_T_max 0.3695 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5340 _diffrn_reflns_av_R_equivalents 0.0165 _diffrn_reflns_av_sigmaI/netI 0.0203 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1978 _reflns_number_gt 1977 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0185P)^2^+3.1536P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 1978 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0177 _refine_ls_R_factor_gt 0.0177 _refine_ls_wR_factor_ref 0.0441 _refine_ls_wR_factor_gt 0.0441 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.181 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.53255(4) 0.15025(6) 0.74026(7) 0.01434(15) Uani 1 1 d . . . Cu2 Cu 0.57154(4) -0.04282(7) 0.92560(8) 0.01495(15) Uani 1 1 d . . . I1 I 0.613150(17) -0.08488(3) 0.67019(4) 0.01287(9) Uani 1 1 d . . . I2 I 0.546531(19) 0.22180(3) 0.99318(4) 0.01650(9) Uani 1 1 d . . . C1 C 0.6083(3) 0.4977(6) 0.7100(6) 0.0180(13) Uani 1 1 d . . . H1A H 0.6616 0.5264 0.7065 0.027 Uiso 1 1 calc R . . H1B H 0.5996 0.4418 0.7915 0.027 Uiso 1 1 calc R . . H1C H 0.5758 0.5804 0.7124 0.027 Uiso 1 1 calc R . . C2 C 0.5899(3) 0.4137(5) 0.5882(6) 0.0133(11) Uani 1 1 d . . . C3 C 0.5563(3) 0.2429(6) 0.4575(6) 0.0180(13) Uani 1 1 d . . . H3 H 0.5389 0.1546 0.4273 0.022 Uiso 1 1 calc R . . C4 C 0.5782(3) 0.3480(5) 0.3753(6) 0.0167(12) Uani 1 1 d . . . H4 H 0.5789 0.3476 0.2792 0.020 Uiso 1 1 calc R . . C5 C 0.6279(3) 0.5917(5) 0.4130(7) 0.0180(12) Uani 1 1 d . . . H5A H 0.6158 0.6631 0.4819 0.022 Uiso 1 1 calc R . . H5B H 0.6017 0.6178 0.3281 0.022 Uiso 1 1 calc R . . C6 C 0.7122(3) 0.5901(7) 0.3886(8) 0.0294(16) Uani 1 1 d . . . H6A H 0.7241 0.5175 0.3209 0.035 Uiso 1 1 calc R . . H6B H 0.7382 0.5649 0.4739 0.035 Uiso 1 1 calc R . . C7 C 0.7429(3) 0.7292(6) 0.3388(7) 0.0254(15) Uani 1 1 d . . . H7A H 0.7292 0.8023 0.4050 0.030 Uiso 1 1 calc R . . H7B H 0.7989 0.7241 0.3351 0.030 Uiso 1 1 calc R . . C8 C 0.7416(4) 0.7044(7) 0.0871(8) 0.0295(15) Uani 1 1 d . . . H8 H 0.7800 0.6354 0.0804 0.035 Uiso 1 1 calc R . . C9 C 0.7018(3) 0.7608(7) -0.0143(9) 0.0295(14) Uani 1 1 d . . . H9 H 0.7070 0.7362 -0.1070 0.035 Uiso 1 1 calc R . . C10 C 0.6616(3) 0.8590(6) 0.1682(8) 0.0231(12) Uani 1 1 d . . . C11 C 0.6214(4) 0.9501(8) 0.2625(8) 0.0366(17) Uani 1 1 d . . . H11A H 0.5906 0.8937 0.3241 0.055 Uiso 1 1 calc R . . H11B H 0.5885 1.0135 0.2116 0.055 Uiso 1 1 calc R . . H11C H 0.6583 1.0042 0.3149 0.055 Uiso 1 1 calc R . . N1 N 0.5628(3) 0.2820(4) 0.5906(5) 0.0132(10) Uani 1 1 d . . . N2 N 0.5991(3) 0.4558(4) 0.4592(5) 0.0141(10) Uani 1 1 d . . . N3 N 0.6517(3) 0.8606(5) 0.0353(6) 0.0245(12) Uani 1 1 d . . . N4 N 0.7147(3) 0.7693(5) 0.2065(5) 0.0244(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0170(3) 0.0144(3) 0.0117(3) 0.0025(3) 0.0001(3) -0.0019(2) Cu2 0.0134(3) 0.0194(3) 0.0121(3) 0.0025(3) -0.0014(3) 0.0047(2) I1 0.01419(16) 0.01108(15) 0.01336(16) -0.00078(16) 0.00231(16) -0.00107(11) I2 0.02036(18) 0.01740(16) 0.01174(17) -0.00425(16) 0.00162(17) -0.00530(13) C1 0.025(3) 0.011(2) 0.018(3) 0.004(2) 0.000(2) -0.001(2) C2 0.014(3) 0.012(3) 0.014(3) 0.002(2) 0.003(2) 0.0038(19) C3 0.022(3) 0.018(3) 0.014(4) -0.004(2) 0.001(2) -0.004(2) C4 0.020(3) 0.017(3) 0.014(3) -0.001(2) 0.003(2) 0.001(2) C5 0.020(3) 0.018(3) 0.017(3) 0.007(3) 0.005(3) -0.001(2) C6 0.019(3) 0.031(3) 0.037(4) 0.023(3) 0.000(3) 0.002(2) C7 0.022(3) 0.033(4) 0.022(4) 0.019(3) -0.009(3) -0.008(2) C8 0.030(4) 0.030(3) 0.029(4) 0.005(3) 0.005(3) 0.007(3) C9 0.023(3) 0.040(4) 0.026(3) -0.008(3) 0.006(3) 0.006(2) C10 0.018(3) 0.027(3) 0.025(3) 0.008(3) -0.004(3) -0.006(2) C11 0.052(5) 0.038(4) 0.020(4) 0.004(3) -0.006(3) 0.014(3) N1 0.014(2) 0.014(2) 0.012(3) 0.0014(19) -0.002(2) -0.0024(16) N2 0.018(2) 0.012(2) 0.012(3) 0.0024(19) 0.0026(19) -0.0015(17) N3 0.017(3) 0.032(3) 0.024(3) 0.010(2) 0.001(2) 0.001(2) N4 0.019(3) 0.030(3) 0.024(3) 0.019(2) -0.012(2) -0.0115(19) _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 N1 2.018(5) . y Cu1 I2 2.6037(8) . y Cu1 Cu2 2.6965(10) . y Cu1 I1 2.7346(7) 2_655 y Cu1 I1 2.7584(7) . y Cu1 Cu2 2.7911(10) 2_655 y Cu2 N3 2.009(5) 1_546 y Cu2 Cu2 2.6545(13) 2_655 y Cu2 I1 2.6591(9) . y Cu2 I2 2.6666(7) . y Cu2 I2 2.7826(7) 2_655 y Cu2 Cu1 2.7911(10) 2_655 y I1 Cu1 2.7346(7) 2_655 y I2 Cu2 2.7826(8) 2_655 y C1 C2 1.485(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N2 1.347(8) . ? C2 N1 1.354(7) . ? C3 C4 1.352(8) . ? C3 N1 1.373(8) . ? C3 H3 0.9500 . ? C4 N2 1.378(7) . ? C4 H4 0.9500 . ? C5 N2 1.473(7) . ? C5 C6 1.507(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.525(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N4 1.451(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.337(10) . ? C8 N4 1.417(9) . ? C8 H8 0.9500 . ? C9 N3 1.394(8) . ? C9 H9 0.9500 . ? C10 N3 1.324(10) . ? C10 N4 1.327(8) . ? C10 C11 1.463(10) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N3 Cu2 2.009(5) 1_564 ? 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 N1 Cu1 I2 120.82(14) . . y N1 Cu1 Cu2 149.52(13) . . ? I2 Cu1 Cu2 60.38(2) . . ? N1 Cu1 I1 101.95(13) . 2_655 y I2 Cu1 I1 113.13(3) . 2_655 y Cu2 Cu1 I1 104.68(3) . 2_655 ? N1 Cu1 I1 101.18(13) . . y I2 Cu1 I1 114.11(3) . . y Cu2 Cu1 I1 58.34(2) . . ? I1 Cu1 I1 103.44(2) 2_655 . y N1 Cu1 Cu2 152.45(13) . 2_655 ? I2 Cu1 Cu2 61.99(2) . 2_655 ? Cu2 Cu1 Cu2 57.83(3) . 2_655 ? I1 Cu1 Cu2 57.52(2) 2_655 2_655 ? I1 Cu1 Cu2 101.57(2) . 2_655 ? N3 Cu2 Cu2 144.34(15) 1_546 2_655 ? N3 Cu2 I1 104.33(16) 1_546 . y Cu2 Cu2 I1 108.031(16) 2_655 . ? N3 Cu2 I2 114.96(16) 1_546 . y Cu2 Cu2 I2 63.06(2) 2_655 . ? I1 Cu2 I2 115.36(3) . . y N3 Cu2 Cu1 149.75(15) 1_546 . ? Cu2 Cu2 Cu1 62.87(2) 2_655 . ? I1 Cu2 Cu1 62.00(2) . . ? I2 Cu2 Cu1 58.09(2) . . ? N3 Cu2 I2 96.42(15) 1_546 2_655 y Cu2 Cu2 I2 58.68(3) 2_655 2_655 ? I1 Cu2 I2 109.90(3) . 2_655 y I2 Cu2 I2 113.95(3) . 2_655 y Cu1 Cu2 I2 113.43(3) . 2_655 ? N3 Cu2 Cu1 130.25(16) 1_546 2_655 ? Cu2 Cu2 Cu1 59.30(2) 2_655 2_655 ? I1 Cu2 Cu1 60.17(2) . 2_655 ? I2 Cu2 Cu1 114.10(3) . 2_655 ? Cu1 Cu2 Cu1 68.98(3) . 2_655 ? I2 Cu2 Cu1 55.70(2) 2_655 2_655 ? Cu2 I1 Cu1 62.31(2) . 2_655 ? Cu2 I1 Cu1 59.67(2) . . ? Cu1 I1 Cu1 68.92(2) 2_655 . ? Cu1 I2 Cu2 61.53(2) . . ? Cu1 I2 Cu2 62.32(2) . 2_655 ? Cu2 I2 Cu2 58.26(2) . 2_655 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 N1 109.9(5) . . ? N2 C2 C1 125.2(5) . . ? N1 C2 C1 124.9(5) . . ? C4 C3 N1 110.3(5) . . ? C4 C3 H3 124.9 . . ? N1 C3 H3 124.9 . . ? C3 C4 N2 106.1(5) . . ? C3 C4 H4 126.9 . . ? N2 C4 H4 126.9 . . ? N2 C5 C6 112.3(5) . . ? N2 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N2 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 113.2(5) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? N4 C7 C6 113.7(5) . . ? N4 C7 H7A 108.8 . . ? C6 C7 H7A 108.8 . . ? N4 C7 H7B 108.8 . . ? C6 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C9 C8 N4 105.6(5) . . ? C9 C8 H8 127.2 . . ? N4 C8 H8 127.2 . . ? C8 C9 N3 110.4(7) . . ? C8 C9 H9 124.8 . . ? N3 C9 H9 124.8 . . ? N3 C10 N4 112.6(6) . . ? N3 C10 C11 124.1(6) . . ? N4 C10 C11 123.3(7) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 N1 C3 105.6(5) . . ? C2 N1 Cu1 133.9(4) . . ? C3 N1 Cu1 120.5(4) . . ? C2 N2 C4 108.1(4) . . ? C2 N2 C5 127.0(5) . . ? C4 N2 C5 124.9(5) . . ? C10 N3 C9 104.9(6) . . ? C10 N3 Cu2 129.3(5) . 1_564 ? C9 N3 Cu2 125.1(5) . 1_564 ? C10 N4 C8 106.5(6) . . ? C10 N4 C7 132.2(7) . . ? C8 N4 C7 121.2(5) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.661 _refine_diff_density_min -0.837 _refine_diff_density_rms 0.127 _database_code_depnum_ccdc_archive 'CCDC 921014' ####################################################################### # # 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_global data_1-160k #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 Cu2 I2 N4' _chemical_formula_weight 585.16 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pnn2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 17.6850(10) _cell_length_b 9.6255(5) _cell_length_c 9.8942(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1684.26(16) _cell_formula_units_Z 4 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 5559 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 30.28 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 6.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3071 _exptl_absorpt_correction_T_max 0.3710 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5397 _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_sigmaI/netI 0.0227 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1989 _reflns_number_gt 1978 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+1.3406P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 1989 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0188 _refine_ls_R_factor_gt 0.0186 _refine_ls_wR_factor_ref 0.0473 _refine_ls_wR_factor_gt 0.0473 _refine_ls_goodness_of_fit_ref 1.137 _refine_ls_restrained_S_all 1.137 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.53275(4) 0.15096(7) 0.74001(7) 0.02304(16) Uani 1 1 d . . . Cu2 Cu 0.57178(4) -0.04307(7) 0.92643(8) 0.02341(16) Uani 1 1 d . . . I1 I 0.612863(17) -0.08494(3) 0.67081(4) 0.01914(9) Uani 1 1 d . . . I2 I 0.54693(2) 0.22149(4) 0.99260(4) 0.02410(10) Uani 1 1 d . . . C1 C 0.6086(3) 0.4968(6) 0.7093(6) 0.0261(14) Uani 1 1 d . . . H1A H 0.6620 0.5242 0.7065 0.039 Uiso 1 1 calc R . . H1B H 0.5992 0.4410 0.7904 0.039 Uiso 1 1 calc R . . H1C H 0.5768 0.5801 0.7114 0.039 Uiso 1 1 calc R . . C2 C 0.5903(3) 0.4138(5) 0.5877(6) 0.0201(12) Uani 1 1 d . . . C3 C 0.5560(4) 0.2434(6) 0.4580(6) 0.0260(14) Uani 1 1 d . . . H3 H 0.5379 0.1556 0.4282 0.031 Uiso 1 1 calc R . . C4 C 0.5786(3) 0.3477(6) 0.3751(6) 0.0269(13) Uani 1 1 d . . . H4 H 0.5799 0.3466 0.2791 0.032 Uiso 1 1 calc R . . C5 C 0.6280(3) 0.5908(5) 0.4127(7) 0.0244(12) Uani 1 1 d . . . H5A H 0.6162 0.6624 0.4813 0.029 Uiso 1 1 calc R . . H5B H 0.6019 0.6168 0.3279 0.029 Uiso 1 1 calc R . . C6 C 0.7118(4) 0.5885(7) 0.3884(8) 0.0390(18) Uani 1 1 d . . . H6A H 0.7236 0.5157 0.3210 0.047 Uiso 1 1 calc R . . H6B H 0.7378 0.5636 0.4737 0.047 Uiso 1 1 calc R . . C7 C 0.7424(4) 0.7270(6) 0.3382(7) 0.0338(16) Uani 1 1 d . . . H7A H 0.7294 0.7999 0.4048 0.041 Uiso 1 1 calc R . . H7B H 0.7982 0.7213 0.3336 0.041 Uiso 1 1 calc R . . C8 C 0.7400(4) 0.7032(7) 0.0873(8) 0.0402(17) Uani 1 1 d . . . H8 H 0.7780 0.6337 0.0804 0.048 Uiso 1 1 calc R . . C9 C 0.7006(4) 0.7589(7) -0.0132(9) 0.0406(16) Uani 1 1 d . . . H9 H 0.7053 0.7334 -0.1055 0.049 Uiso 1 1 calc R . . C10 C 0.6618(3) 0.8577(6) 0.1683(8) 0.0302(13) Uani 1 1 d . . . C11 C 0.6220(5) 0.9499(8) 0.2611(8) 0.049(2) Uani 1 1 d . . . H11A H 0.5872 0.8954 0.3171 0.074 Uiso 1 1 calc R . . H11B H 0.5933 1.0189 0.2094 0.074 Uiso 1 1 calc R . . H11C H 0.6587 0.9973 0.3193 0.074 Uiso 1 1 calc R . . N1 N 0.5630(3) 0.2820(4) 0.5901(5) 0.0204(10) Uani 1 1 d . . . N2 N 0.5992(3) 0.4560(5) 0.4592(5) 0.0203(10) Uani 1 1 d . . . N3 N 0.6515(3) 0.8599(5) 0.0355(6) 0.0313(12) Uani 1 1 d . . . N4 N 0.7140(3) 0.7684(5) 0.2069(6) 0.0320(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0280(3) 0.0220(3) 0.0191(4) 0.0031(3) 0.0002(3) -0.0033(3) Cu2 0.0220(4) 0.0287(4) 0.0195(3) 0.0032(3) -0.0023(3) 0.0074(3) I1 0.02163(17) 0.01642(15) 0.01937(17) -0.00144(16) 0.00317(16) -0.00169(11) I2 0.0299(2) 0.02423(17) 0.01818(17) -0.00544(16) 0.00132(17) -0.00614(13) C1 0.038(3) 0.016(2) 0.024(4) 0.004(2) 0.001(3) -0.005(2) C2 0.021(3) 0.016(3) 0.023(3) 0.000(2) 0.004(2) 0.0030(19) C3 0.034(3) 0.024(3) 0.020(4) -0.005(2) 0.003(2) -0.005(2) C4 0.036(3) 0.028(3) 0.017(3) -0.003(3) 0.005(3) 0.002(3) C5 0.027(3) 0.024(3) 0.021(3) 0.005(2) 0.006(3) 0.000(2) C6 0.024(3) 0.042(4) 0.051(5) 0.029(3) 0.002(3) 0.008(3) C7 0.031(3) 0.039(4) 0.031(4) 0.023(3) -0.011(3) -0.006(3) C8 0.041(4) 0.040(4) 0.039(4) 0.008(3) 0.006(3) 0.014(3) C9 0.039(4) 0.048(4) 0.034(4) -0.010(4) 0.006(4) 0.013(3) C10 0.026(3) 0.034(3) 0.031(3) 0.013(3) -0.002(3) -0.002(2) C11 0.070(5) 0.051(4) 0.027(4) 0.007(3) -0.003(4) 0.022(4) N1 0.023(2) 0.017(2) 0.022(3) 0.001(2) -0.001(2) -0.0030(17) N2 0.029(2) 0.017(2) 0.015(3) 0.0026(19) 0.0013(19) -0.0009(18) N3 0.022(3) 0.040(3) 0.032(3) 0.011(3) -0.002(2) 0.000(2) N4 0.026(3) 0.040(3) 0.031(3) 0.022(2) -0.012(2) -0.009(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.019(5) . ? Cu1 I2 2.6018(8) . ? Cu1 Cu2 2.7142(10) . ? Cu1 I1 2.7393(7) 2_655 ? Cu1 I1 2.7626(7) . ? Cu1 Cu2 2.8103(10) 2_655 ? Cu2 N3 2.006(5) 1_546 ? Cu2 I1 2.6621(9) . ? Cu2 I2 2.6658(8) . ? Cu2 Cu2 2.6709(13) 2_655 ? Cu2 I2 2.7902(8) 2_655 ? Cu2 Cu1 2.8103(10) 2_655 ? I1 Cu1 2.7393(7) 2_655 ? I2 Cu2 2.7902(8) 2_655 ? C1 C2 1.480(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N2 1.344(8) . ? C2 N1 1.358(7) . ? C3 C4 1.357(9) . ? C3 N1 1.364(8) . ? C3 H3 0.9500 . ? C4 N2 1.383(8) . ? C4 H4 0.9500 . ? C5 N2 1.467(7) . ? C5 C6 1.502(9) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.522(8) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N4 1.449(8) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.327(11) . ? C8 N4 1.417(9) . ? C8 H8 0.9500 . ? C9 N3 1.390(8) . ? C9 H9 0.9500 . ? C10 N4 1.317(8) . ? C10 N3 1.327(10) . ? C10 C11 1.458(10) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N3 Cu2 2.006(5) 1_564 ? 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 N1 Cu1 I2 121.14(14) . . ? N1 Cu1 Cu2 149.52(14) . . ? I2 Cu1 Cu2 60.15(2) . . ? N1 Cu1 I1 102.13(14) . 2_655 ? I2 Cu1 I1 113.03(3) . 2_655 ? Cu2 Cu1 I1 104.44(3) . 2_655 ? N1 Cu1 I1 101.28(14) . . ? I2 Cu1 I1 113.77(3) . . ? Cu2 Cu1 I1 58.16(2) . . ? I1 Cu1 I1 103.27(2) 2_655 . ? N1 Cu1 Cu2 152.51(14) . 2_655 ? I2 Cu1 Cu2 61.93(2) . 2_655 ? Cu2 Cu1 Cu2 57.79(3) . 2_655 ? I1 Cu1 Cu2 57.31(2) 2_655 2_655 ? I1 Cu1 Cu2 101.32(3) . 2_655 ? N3 Cu2 I1 104.42(16) 1_546 . ? N3 Cu2 I2 115.37(16) 1_546 . ? I1 Cu2 I2 115.02(3) . . ? N3 Cu2 Cu2 144.33(15) 1_546 2_655 ? I1 Cu2 Cu2 107.844(16) . 2_655 ? I2 Cu2 Cu2 63.04(3) . 2_655 ? N3 Cu2 Cu1 149.86(15) 1_546 . ? I1 Cu2 Cu1 61.83(2) . . ? I2 Cu2 Cu1 57.84(2) . . ? Cu2 Cu2 Cu1 62.91(3) 2_655 . ? N3 Cu2 I2 96.64(15) 1_546 2_655 ? I1 Cu2 I2 109.58(3) . 2_655 ? I2 Cu2 I2 113.97(3) . 2_655 ? Cu2 Cu2 I2 58.39(3) 2_655 2_655 ? Cu1 Cu2 I2 113.05(3) . 2_655 ? N3 Cu2 Cu1 130.03(16) 1_546 2_655 ? I1 Cu2 Cu1 60.00(2) . 2_655 ? I2 Cu2 Cu1 113.94(3) . 2_655 ? Cu2 Cu2 Cu1 59.30(3) 2_655 2_655 ? Cu1 Cu2 Cu1 68.96(3) . 2_655 ? I2 Cu2 Cu1 55.36(2) 2_655 2_655 ? Cu2 I1 Cu1 62.68(2) . 2_655 ? Cu2 I1 Cu1 60.01(2) . . ? Cu1 I1 Cu1 69.31(2) 2_655 . ? Cu1 I2 Cu2 62.01(2) . . ? Cu1 I2 Cu2 62.71(2) . 2_655 ? Cu2 I2 Cu2 58.57(3) . 2_655 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 N1 109.9(5) . . ? N2 C2 C1 125.5(5) . . ? N1 C2 C1 124.6(5) . . ? C4 C3 N1 110.6(5) . . ? C4 C3 H3 124.7 . . ? N1 C3 H3 124.7 . . ? C3 C4 N2 105.8(5) . . ? C3 C4 H4 127.1 . . ? N2 C4 H4 127.1 . . ? N2 C5 C6 112.3(5) . . ? N2 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N2 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 113.0(5) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? N4 C7 C6 114.2(5) . . ? N4 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? N4 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 N4 106.0(6) . . ? C9 C8 H8 127.0 . . ? N4 C8 H8 127.0 . . ? C8 C9 N3 110.6(7) . . ? C8 C9 H9 124.7 . . ? N3 C9 H9 124.7 . . ? N4 C10 N3 113.2(6) . . ? N4 C10 C11 123.6(7) . . ? N3 C10 C11 123.2(6) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 N1 C3 105.6(5) . . ? C2 N1 Cu1 133.7(4) . . ? C3 N1 Cu1 120.7(4) . . ? C2 N2 C4 108.1(5) . . ? C2 N2 C5 127.2(5) . . ? C4 N2 C5 124.7(5) . . ? C10 N3 C9 104.3(6) . . ? C10 N3 Cu2 129.6(5) . 1_564 ? C9 N3 Cu2 125.3(5) . 1_564 ? C10 N4 C8 106.0(6) . . ? C10 N4 C7 133.0(7) . . ? C8 N4 C7 120.9(5) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.548 _refine_diff_density_min -0.701 _refine_diff_density_rms 0.138 _database_code_depnum_ccdc_archive 'CCDC 921015' ####################################################################### # # 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_global data_1-220K #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 Cu2 I2 N4' _chemical_formula_weight 585.16 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pnn2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 17.7336(11) _cell_length_b 9.6470(6) _cell_length_c 9.9065(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1694.76(18) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 5087 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.44 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.293 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 6.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3088 _exptl_absorpt_correction_T_max 0.3729 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5437 _diffrn_reflns_av_R_equivalents 0.0188 _diffrn_reflns_av_sigmaI/netI 0.0217 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1996 _reflns_number_gt 1979 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0337P)^2^+0.2236P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 1996 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0199 _refine_ls_R_factor_gt 0.0196 _refine_ls_wR_factor_ref 0.0515 _refine_ls_wR_factor_gt 0.0513 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.53300(4) 0.15158(7) 0.73968(8) 0.03258(17) Uani 1 1 d . . . Cu2 Cu 0.57207(4) -0.04345(8) 0.92725(8) 0.03272(17) Uani 1 1 d . . . I1 I 0.612612(18) -0.08502(3) 0.67139(4) 0.02585(10) Uani 1 1 d . . . I2 I 0.54732(2) 0.22095(4) 0.99200(4) 0.03209(11) Uani 1 1 d . . . C1 C 0.6085(4) 0.4961(6) 0.7093(6) 0.0363(15) Uani 1 1 d . . . H1A H 0.6610 0.5240 0.7067 0.054 Uiso 1 1 calc R . . H1B H 0.5995 0.4404 0.7893 0.054 Uiso 1 1 calc R . . H1C H 0.5767 0.5778 0.7119 0.054 Uiso 1 1 calc R . . C2 C 0.5906(3) 0.4138(5) 0.5877(6) 0.0257(12) Uani 1 1 d . . . C3 C 0.5562(4) 0.2429(7) 0.4576(7) 0.0352(16) Uani 1 1 d . . . H3 H 0.5388 0.1560 0.4281 0.042 Uiso 1 1 calc R . . C4 C 0.5780(3) 0.3476(6) 0.3760(7) 0.0352(14) Uani 1 1 d . . . H4 H 0.5787 0.3469 0.2811 0.042 Uiso 1 1 calc R . . C5 C 0.6280(3) 0.5901(5) 0.4128(7) 0.0309(13) Uani 1 1 d . . . H5A H 0.6168 0.6608 0.4810 0.037 Uiso 1 1 calc R . . H5B H 0.6019 0.6162 0.3294 0.037 Uiso 1 1 calc R . . C6 C 0.7114(4) 0.5877(7) 0.3873(9) 0.0481(19) Uani 1 1 d . . . H6A H 0.7226 0.5160 0.3201 0.058 Uiso 1 1 calc R . . H6B H 0.7374 0.5625 0.4711 0.058 Uiso 1 1 calc R . . C7 C 0.7421(4) 0.7251(7) 0.3375(8) 0.0439(18) Uani 1 1 d . . . H7A H 0.7296 0.7971 0.4037 0.053 Uiso 1 1 calc R . . H7B H 0.7972 0.7188 0.3325 0.053 Uiso 1 1 calc R . . C8 C 0.7391(4) 0.7007(8) 0.0867(9) 0.0538(19) Uani 1 1 d . . . H8 H 0.7761 0.6314 0.0793 0.065 Uiso 1 1 calc R . . C9 C 0.7001(4) 0.7569(8) -0.0110(10) 0.0517(18) Uani 1 1 d . . . H9 H 0.7047 0.7317 -0.1023 0.062 Uiso 1 1 calc R . . C10 C 0.6618(3) 0.8578(6) 0.1684(8) 0.0382(14) Uani 1 1 d . . . C11 C 0.6236(5) 0.9508(9) 0.2617(9) 0.066(2) Uani 1 1 d . . . H11A H 0.5876 0.8987 0.3152 0.098 Uiso 1 1 calc R . . H11B H 0.5973 1.0221 0.2112 0.098 Uiso 1 1 calc R . . H11C H 0.6605 0.9936 0.3209 0.098 Uiso 1 1 calc R . . N1 N 0.5633(3) 0.2827(4) 0.5901(6) 0.0279(11) Uani 1 1 d . . . N2 N 0.5991(3) 0.4559(5) 0.4592(5) 0.0280(11) Uani 1 1 d . . . N3 N 0.6511(3) 0.8582(6) 0.0361(6) 0.0405(13) Uani 1 1 d . . . N4 N 0.7135(3) 0.7671(6) 0.2066(6) 0.0410(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0398(4) 0.0309(4) 0.0270(4) 0.0041(3) 0.0001(3) -0.0048(3) Cu2 0.0317(4) 0.0396(4) 0.0269(4) 0.0032(3) -0.0038(3) 0.0106(3) I1 0.02946(18) 0.02255(16) 0.02555(18) -0.00198(17) 0.00391(17) -0.00219(12) I2 0.0398(2) 0.03164(19) 0.02487(18) -0.00667(17) 0.00079(18) -0.00666(14) C1 0.056(4) 0.022(3) 0.031(4) 0.005(2) 0.000(3) -0.007(2) C2 0.030(3) 0.018(3) 0.029(3) -0.002(2) 0.005(3) 0.0037(19) C3 0.046(4) 0.029(3) 0.030(4) -0.007(3) 0.003(3) -0.006(2) C4 0.044(4) 0.038(3) 0.024(3) -0.006(3) 0.005(3) -0.002(3) C5 0.033(3) 0.027(3) 0.033(3) 0.009(3) 0.007(3) 0.001(2) C6 0.031(3) 0.052(4) 0.061(5) 0.034(4) 0.000(3) 0.004(3) C7 0.034(3) 0.056(4) 0.042(4) 0.029(3) -0.008(3) -0.009(3) C8 0.055(4) 0.055(4) 0.051(5) 0.008(4) 0.005(4) 0.022(3) C9 0.048(4) 0.063(4) 0.043(4) -0.007(4) 0.008(4) 0.017(3) C10 0.037(3) 0.037(3) 0.041(3) 0.011(4) -0.006(3) -0.002(2) C11 0.093(7) 0.067(5) 0.037(5) 0.007(4) -0.002(4) 0.031(5) N1 0.029(2) 0.024(2) 0.031(3) 0.000(2) -0.002(2) -0.0025(17) N2 0.037(3) 0.025(2) 0.022(3) 0.003(2) 0.003(2) -0.0031(19) N3 0.029(3) 0.057(3) 0.036(3) 0.013(3) 0.001(2) 0.001(2) N4 0.032(3) 0.047(3) 0.044(4) 0.026(3) -0.016(2) -0.013(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.021(5) . y Cu1 I2 2.6000(9) . y Cu1 Cu2 2.7336(11) . y Cu1 I1 2.7455(8) 2_655 y Cu1 I1 2.7678(8) . y Cu1 Cu2 2.8307(11) 2_655 y Cu2 N3 2.006(5) 1_546 y Cu2 I1 2.6651(10) . y Cu2 I2 2.6664(8) . y Cu2 Cu2 2.6902(14) 2_655 y Cu2 I2 2.7976(8) 2_655 y Cu2 Cu1 2.8307(11) 2_655 ? I1 Cu1 2.7455(8) 2_655 ? I2 Cu2 2.7976(8) 2_655 ? C1 C2 1.477(8) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? C2 N2 1.345(8) . ? C2 N1 1.354(7) . ? C3 C4 1.350(9) . ? C3 N1 1.374(9) . ? C3 H3 0.9400 . ? C4 N2 1.383(8) . ? C4 H4 0.9400 . ? C5 N2 1.466(7) . ? C5 C6 1.501(9) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C7 1.515(8) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 N4 1.451(8) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 C9 1.307(12) . ? C8 N4 1.424(10) . ? C8 H8 0.9400 . ? C9 N3 1.389(9) . ? C9 H9 0.9400 . ? C10 N4 1.322(8) . ? C10 N3 1.324(10) . ? C10 C11 1.456(11) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? N3 Cu2 2.006(5) 1_564 ? 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 N1 Cu1 I2 121.18(15) . . ? N1 Cu1 Cu2 149.51(14) . . ? I2 Cu1 Cu2 59.93(2) . . ? N1 Cu1 I1 102.46(14) . 2_655 ? I2 Cu1 I1 112.89(3) . 2_655 ? Cu2 Cu1 I1 104.18(3) . 2_655 ? N1 Cu1 I1 101.62(14) . . ? I2 Cu1 I1 113.42(3) . . ? Cu2 Cu1 I1 57.95(2) . . ? I1 Cu1 I1 103.10(3) 2_655 . ? N1 Cu1 Cu2 152.49(14) . 2_655 ? I2 Cu1 Cu2 61.84(2) . 2_655 ? Cu2 Cu1 Cu2 57.79(3) . 2_655 ? I1 Cu1 Cu2 57.08(2) 2_655 2_655 ? I1 Cu1 Cu2 101.09(3) . 2_655 ? N3 Cu2 I1 104.58(17) 1_546 . ? N3 Cu2 I2 115.97(18) 1_546 . ? I1 Cu2 I2 114.66(3) . . ? N3 Cu2 Cu2 144.17(16) 1_546 2_655 ? I1 Cu2 Cu2 107.650(17) . 2_655 ? I2 Cu2 Cu2 62.97(3) . 2_655 ? N3 Cu2 Cu1 150.21(16) 1_546 . ? I1 Cu2 Cu1 61.67(2) . . ? I2 Cu2 Cu1 57.55(2) . . ? Cu2 Cu2 Cu1 62.91(3) 2_655 . ? N3 Cu2 I2 96.65(16) 1_546 2_655 ? I1 Cu2 I2 109.27(3) . 2_655 ? I2 Cu2 I2 113.94(3) . 2_655 ? Cu2 Cu2 I2 58.10(3) 2_655 2_655 ? Cu1 Cu2 I2 112.66(3) . 2_655 ? N3 Cu2 Cu1 129.66(18) 1_546 2_655 ? I1 Cu2 Cu1 59.85(2) . 2_655 ? I2 Cu2 Cu1 113.71(3) . 2_655 ? Cu2 Cu2 Cu1 59.29(3) 2_655 2_655 ? Cu1 Cu2 Cu1 68.94(3) . 2_655 ? I2 Cu2 Cu1 55.02(2) 2_655 2_655 ? Cu2 I1 Cu1 63.07(2) . 2_655 ? Cu2 I1 Cu1 60.38(2) . . ? Cu1 I1 Cu1 69.69(3) 2_655 . ? Cu1 I2 Cu2 62.53(2) . . ? Cu1 I2 Cu2 63.14(2) . 2_655 ? Cu2 I2 Cu2 58.93(3) . 2_655 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N2 C2 N1 109.8(5) . . ? N2 C2 C1 125.9(5) . . ? N1 C2 C1 124.3(5) . . ? C4 C3 N1 109.7(5) . . ? C4 C3 H3 125.2 . . ? N1 C3 H3 125.2 . . ? C3 C4 N2 106.6(6) . . ? C3 C4 H4 126.7 . . ? N2 C4 H4 126.7 . . ? N2 C5 C6 112.5(5) . . ? N2 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N2 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C5 C6 C7 113.3(5) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? N4 C7 C6 114.2(6) . . ? N4 C7 H7A 108.7 . . ? C6 C7 H7A 108.7 . . ? N4 C7 H7B 108.7 . . ? C6 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C9 C8 N4 105.2(6) . . ? C9 C8 H8 127.4 . . ? N4 C8 H8 127.4 . . ? C8 C9 N3 111.9(8) . . ? C8 C9 H9 124.0 . . ? N3 C9 H9 124.0 . . ? N4 C10 N3 112.7(7) . . ? N4 C10 C11 123.3(7) . . ? N3 C10 C11 124.0(6) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 N1 C3 106.1(5) . . ? C2 N1 Cu1 133.8(4) . . ? C3 N1 Cu1 120.1(4) . . ? C2 N2 C4 107.8(5) . . ? C2 N2 C5 127.1(5) . . ? C4 N2 C5 125.1(5) . . ? C10 N3 C9 103.9(6) . . ? C10 N3 Cu2 129.3(5) . 1_564 ? C9 N3 Cu2 126.1(5) . 1_564 ? C10 N4 C8 106.2(6) . . ? C10 N4 C7 133.1(7) . . ? C8 N4 C7 120.6(6) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.439 _refine_diff_density_min -0.654 _refine_diff_density_rms 0.128 _database_code_depnum_ccdc_archive 'CCDC 921016' ####################################################################### # # 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_global data_1-298K #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H16 Cu2 I2 N4' _chemical_formula_weight 585.16 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' 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pnn2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, z+1/2' _cell_length_a 17.9821(13) _cell_length_b 9.7493(7) _cell_length_c 10.0256(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1757.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4527 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 27.00 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.211 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 5.925 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3189 _exptl_absorpt_correction_T_max 0.3837 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5617 _diffrn_reflns_av_R_equivalents 0.0193 _diffrn_reflns_av_sigmaI/netI 0.0233 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2094 _reflns_number_gt 2059 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+0.0854P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(3) _refine_ls_number_reflns 2094 _refine_ls_number_parameters 174 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0215 _refine_ls_wR_factor_ref 0.0577 _refine_ls_wR_factor_gt 0.0574 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.105 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.46670(5) 0.84784(8) 0.26075(9) 0.0482(2) Uani 1 1 d . . . Cu2 Cu 0.42740(5) 1.04403(9) 0.07203(9) 0.0480(2) Uani 1 1 d . . . I1 I 0.387659(19) 1.08528(3) 0.32790(5) 0.03664(11) Uani 1 1 d . . . I2 I 0.45205(2) 0.78001(4) 0.00884(5) 0.04510(12) Uani 1 1 d . . . C1 C 0.3917(4) 0.5048(7) 0.2921(7) 0.0512(19) Uani 1 1 d . . . H1A H 0.3404 0.4778 0.2953 0.077 Uiso 1 1 calc R . . H1B H 0.4226 0.4246 0.2900 0.077 Uiso 1 1 calc R . . H1C H 0.4003 0.5586 0.2134 0.077 Uiso 1 1 calc R . . C2 C 0.4098(4) 0.5876(5) 0.4119(7) 0.0365(13) Uani 1 1 d . . . C3 C 0.4439(4) 0.7561(7) 0.5421(7) 0.0481(18) Uani 1 1 d . . . H3 H 0.4617 0.8407 0.5708 0.058 Uiso 1 1 calc R . . C4 C 0.4218(4) 0.6536(7) 0.6237(8) 0.0514(17) Uani 1 1 d . . . H4 H 0.4209 0.6550 0.7164 0.062 Uiso 1 1 calc R . . C5 C 0.3719(4) 0.4109(6) 0.5878(8) 0.0464(16) Uani 1 1 d . . . H5A H 0.3975 0.3858 0.6694 0.056 Uiso 1 1 calc R . . H5B H 0.3827 0.3412 0.5215 0.056 Uiso 1 1 calc R . . C6 C 0.2889(4) 0.4138(8) 0.6136(10) 0.065(2) Uani 1 1 d . . . H6A H 0.2634 0.4383 0.5317 0.078 Uiso 1 1 calc R . . H6B H 0.2781 0.4842 0.6792 0.078 Uiso 1 1 calc R . . C7 C 0.2589(4) 0.2767(7) 0.6635(8) 0.056(2) Uani 1 1 d . . . H7A H 0.2051 0.2826 0.6689 0.067 Uiso 1 1 calc R . . H7B H 0.2709 0.2064 0.5986 0.067 Uiso 1 1 calc R . . C8 C 0.2627(5) 0.3019(9) 0.9141(10) 0.071(2) Uani 1 1 d . . . H8 H 0.2270 0.3706 0.9217 0.085 Uiso 1 1 calc R . . C9 C 0.3018(4) 0.2450(9) 1.0122(11) 0.068(2) Uani 1 1 d . . . H9 H 0.2983 0.2698 1.1016 0.082 Uiso 1 1 calc R . . C10 C 0.3380(3) 0.1435(6) 0.8321(9) 0.0498(15) Uani 1 1 d . . . C11 C 0.3744(7) 0.0480(12) 0.7398(10) 0.091(3) Uani 1 1 d . . . H11B H 0.4170 0.0917 0.7006 0.137 Uiso 1 1 calc R . . H11C H 0.3401 0.0223 0.6709 0.137 Uiso 1 1 calc R . . H11A H 0.3900 -0.0323 0.7876 0.137 Uiso 1 1 calc R . . N1 N 0.4363(3) 0.7179(5) 0.4105(6) 0.0387(12) Uani 1 1 d . . . N2 N 0.4005(3) 0.5445(5) 0.5405(5) 0.0409(12) Uani 1 1 d . . . N3 N 0.3489(3) 0.1427(6) 0.9629(6) 0.0528(15) Uani 1 1 d . . . N4 N 0.2874(3) 0.2345(6) 0.7926(7) 0.0550(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0605(5) 0.0442(4) 0.0398(4) 0.0049(4) 0.0005(4) -0.0074(3) Cu2 0.0482(5) 0.0563(5) 0.0396(4) 0.0044(4) -0.0058(4) 0.0143(4) I1 0.0420(2) 0.03194(18) 0.03593(19) -0.00264(18) 0.00533(18) -0.00301(13) I2 0.0558(3) 0.0434(2) 0.0361(2) -0.00834(19) 0.0004(2) -0.00782(16) C1 0.080(5) 0.028(3) 0.046(5) 0.003(3) -0.006(3) -0.010(3) C2 0.042(3) 0.030(3) 0.037(4) 0.001(3) 0.001(3) 0.003(2) C3 0.065(4) 0.041(3) 0.038(5) -0.009(3) 0.009(3) -0.009(3) C4 0.068(4) 0.054(4) 0.033(4) -0.008(3) 0.012(3) 0.000(3) C5 0.051(4) 0.041(3) 0.047(4) 0.013(3) 0.009(3) 0.002(2) C6 0.051(4) 0.069(5) 0.075(6) 0.041(4) 0.002(4) 0.009(3) C7 0.049(4) 0.068(5) 0.051(5) 0.031(4) -0.014(4) -0.006(3) C8 0.070(5) 0.076(5) 0.066(6) 0.012(4) 0.013(5) 0.029(4) C9 0.070(5) 0.079(5) 0.056(5) -0.006(5) 0.000(5) 0.027(4) C10 0.050(3) 0.050(3) 0.050(4) 0.007(4) -0.001(4) 0.001(2) C11 0.129(9) 0.097(7) 0.048(6) 0.007(5) 0.002(6) 0.037(6) N1 0.045(3) 0.031(3) 0.041(3) 0.003(2) 0.002(2) -0.0049(19) N2 0.054(3) 0.038(3) 0.031(3) 0.001(2) 0.009(2) -0.002(2) N3 0.039(3) 0.069(4) 0.050(4) 0.011(3) -0.003(3) 0.004(2) N4 0.043(3) 0.066(3) 0.057(5) 0.033(3) -0.017(3) -0.012(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 2.039(5) . y Cu1 I2 2.6240(10) . y Cu1 I1 2.7815(9) 2_675 y Cu1 Cu2 2.7817(12) . y Cu1 I1 2.7986(9) . y Cu1 Cu2 2.8840(12) 2_675 y Cu2 N3 2.029(6) 1_564 y Cu2 I2 2.6877(10) . y Cu2 I1 2.6931(11) . y Cu2 Cu2 2.7486(16) 2_675 y Cu2 I2 2.8361(10) 2_675 y Cu2 Cu1 2.8840(12) 2_675 ? I1 Cu1 2.7815(9) 2_675 ? I2 Cu2 2.8361(10) 2_675 ? C1 C2 1.483(9) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.357(7) . ? C2 N2 1.366(8) . ? C3 C4 1.351(11) . ? C3 N1 1.378(10) . ? C3 H3 0.9300 . ? C4 N2 1.405(9) . ? C4 H4 0.9300 . ? C5 N2 1.479(8) . ? C5 C6 1.515(10) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N4 1.452(9) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.331(13) . ? C8 N4 1.453(11) . ? C8 H8 0.9300 . ? C9 N3 1.398(10) . ? C9 H9 0.9300 . ? C10 N3 1.326(11) . ? C10 N4 1.331(9) . ? C10 C11 1.467(13) . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C11 H11A 0.9600 . ? N3 Cu2 2.029(6) 1_546 ? 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 N1 Cu1 I2 121.68(16) . . ? N1 Cu1 I1 102.71(16) . 2_675 ? I2 Cu1 I1 112.74(3) . 2_675 ? N1 Cu1 Cu2 149.29(15) . . ? I2 Cu1 Cu2 59.54(3) . . ? I1 Cu1 Cu2 104.04(3) 2_675 . ? N1 Cu1 I1 101.57(15) . . ? I2 Cu1 I1 112.89(3) . . ? I1 Cu1 I1 103.07(3) 2_675 . ? Cu2 Cu1 I1 57.71(3) . . ? N1 Cu1 Cu2 152.53(15) . 2_675 ? I2 Cu1 Cu2 61.77(3) . 2_675 ? I1 Cu1 Cu2 56.73(3) 2_675 2_675 ? Cu2 Cu1 Cu2 58.01(4) . 2_675 ? I1 Cu1 Cu2 101.00(3) . 2_675 ? N3 Cu2 I2 116.24(19) 1_564 . ? N3 Cu2 I1 104.95(18) 1_564 . ? I2 Cu2 I1 114.29(3) . . ? N3 Cu2 Cu2 144.02(17) 1_564 2_675 ? I2 Cu2 Cu2 62.88(3) . 2_675 ? I1 Cu2 Cu2 107.380(19) . 2_675 ? N3 Cu2 Cu1 150.43(17) 1_564 . ? I2 Cu2 Cu1 57.31(3) . . ? I1 Cu2 Cu1 61.46(3) . . ? Cu2 Cu2 Cu1 62.86(3) 2_675 . ? N3 Cu2 I2 97.15(17) 1_564 2_675 ? I2 Cu2 I2 113.61(3) . 2_675 ? I1 Cu2 I2 108.98(3) . 2_675 ? Cu2 Cu2 I2 57.51(3) 2_675 2_675 ? Cu1 Cu2 I2 111.94(3) . 2_675 ? N3 Cu2 Cu1 129.77(19) 1_564 2_675 ? I2 Cu2 Cu1 113.32(3) . 2_675 ? I1 Cu2 Cu1 59.72(3) . 2_675 ? Cu2 Cu2 Cu1 59.13(3) 2_675 2_675 ? Cu1 Cu2 Cu1 68.74(4) . 2_675 ? I2 Cu2 Cu1 54.60(3) 2_675 2_675 ? Cu2 I1 Cu1 63.55(3) . 2_675 ? Cu2 I1 Cu1 60.83(3) . . ? Cu1 I1 Cu1 69.97(3) 2_675 . ? Cu1 I2 Cu2 63.15(3) . . ? Cu1 I2 Cu2 63.63(3) . 2_675 ? Cu2 I2 Cu2 59.61(3) . 2_675 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 109.8(6) . . ? N1 C2 C1 125.3(6) . . ? N2 C2 C1 124.8(5) . . ? C4 C3 N1 110.5(6) . . ? C4 C3 H3 124.8 . . ? N1 C3 H3 124.8 . . ? C3 C4 N2 106.3(6) . . ? C3 C4 H4 126.8 . . ? N2 C4 H4 126.8 . . ? N2 C5 C6 112.4(5) . . ? N2 C5 H5A 109.1 . . ? C6 C5 H5A 109.1 . . ? N2 C5 H5B 109.1 . . ? C6 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 112.8(6) . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? C7 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? N4 C7 C6 114.6(6) . . ? N4 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? N4 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C9 C8 N4 105.6(7) . . ? C9 C8 H8 127.2 . . ? N4 C8 H8 127.2 . . ? C8 C9 N3 110.9(9) . . ? C8 C9 H9 124.6 . . ? N3 C9 H9 124.6 . . ? N3 C10 N4 113.5(7) . . ? N3 C10 C11 123.7(7) . . ? N4 C10 C11 122.7(8) . . ? C10 C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? C2 N1 C3 106.2(6) . . ? C2 N1 Cu1 133.1(5) . . ? C3 N1 Cu1 120.7(4) . . ? C2 N2 C4 107.1(5) . . ? C2 N2 C5 128.0(6) . . ? C4 N2 C5 124.9(6) . . ? C10 N3 C9 104.8(7) . . ? C10 N3 Cu2 129.7(5) . 1_546 ? C9 N3 Cu2 124.7(6) . 1_546 ? C10 N4 C7 134.1(8) . . ? C10 N4 C8 105.1(6) . . ? C7 N4 C8 120.7(6) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.552 _refine_diff_density_min -0.760 _refine_diff_density_rms 0.159 _database_code_depnum_ccdc_archive 'CCDC 921017' ####################################################################### # # 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_global data_2-100K #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Cu3 I3 N6' _chemical_formula_weight 856.70 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.146(3) _cell_length_b 11.2465(14) _cell_length_c 16.080(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.206(2) _cell_angle_gamma 90.00 _cell_volume 4460.9(10) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2060 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 27.26 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.551 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3192 _exptl_absorpt_coefficient_mu 7.000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5412 _exptl_absorpt_correction_T_max 0.6043 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8628 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3894 _reflns_number_gt 2900 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0473P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3894 _refine_ls_number_parameters 280 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1017 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 0.02026(5) 0.72487(9) -0.16045(7) 0.0199(3) Uani 1 1 d . . . Cu2 Cu -0.05149(4) 0.56658(9) -0.23564(7) 0.0179(3) Uani 1 1 d . . . Cu3 Cu -0.25489(5) 0.29187(9) 0.42860(7) 0.0198(3) Uani 1 1 d . . . I1 I -0.08392(2) 0.79409(5) -0.23456(4) 0.01815(16) Uani 1 1 d . . . I2 I 0.03696(2) 0.49288(5) -0.11668(3) 0.01843(16) Uani 1 1 d . . . I3 I -0.16198(2) 0.20822(5) 0.50055(4) 0.02109(17) Uani 1 1 d . . . C1 C -0.1157(4) 0.4717(8) -0.1153(6) 0.024(2) Uani 1 1 d . . . H1 H -0.1023 0.5332 -0.0764 0.028 Uiso 1 1 calc R . . C2 C -0.1331(3) 0.3663(8) -0.2276(6) 0.021(2) Uani 1 1 d . . . H2 H -0.1341 0.3382 -0.2836 0.025 Uiso 1 1 calc R . . C3 C -0.1579(4) 0.3119(8) -0.1688(6) 0.022(2) Uani 1 1 d . . . H3 H -0.1790 0.2413 -0.1767 0.026 Uiso 1 1 calc R . . C4 C -0.1651(4) 0.3612(8) -0.0191(5) 0.022(2) Uani 1 1 d . . . H4A H -0.1383 0.3944 0.0286 0.027 Uiso 1 1 calc R . . H4B H -0.1685 0.2750 -0.0089 0.027 Uiso 1 1 calc R . . C5 C -0.2201(3) 0.4217(7) -0.0225(5) 0.019(2) Uani 1 1 d . . . H5A H -0.2158 0.5084 -0.0297 0.023 Uiso 1 1 calc R . . H5B H -0.2459 0.3921 -0.0727 0.023 Uiso 1 1 calc R . . C6 C -0.2438(4) 0.3998(8) 0.0566(5) 0.019(2) Uani 1 1 d . . . H6A H -0.2822 0.4254 0.0454 0.023 Uiso 1 1 calc R . . H6B H -0.2428 0.3135 0.0690 0.023 Uiso 1 1 calc R . . C7 C -0.2131(4) 0.4660(8) 0.1335(5) 0.025(2) Uani 1 1 d . . . H7A H -0.1756 0.4351 0.1487 0.030 Uiso 1 1 calc R . . H7B H -0.2112 0.5516 0.1201 0.030 Uiso 1 1 calc R . . C8 C -0.2893(4) 0.5023(8) 0.2150(5) 0.021(2) Uani 1 1 d . . . H8 H -0.3099 0.5594 0.1789 0.025 Uiso 1 1 calc R . . C9 C -0.3013(4) 0.4542(8) 0.2871(5) 0.019(2) Uani 1 1 d . . . H9 H -0.3322 0.4732 0.3103 0.023 Uiso 1 1 calc R . . C10 C -0.2259(4) 0.3737(8) 0.2708(6) 0.022(2) Uani 1 1 d . . . H10 H -0.1940 0.3264 0.2795 0.026 Uiso 1 1 calc R . . C11 C 0.0723(4) 0.9024(7) -0.0216(5) 0.019(2) Uani 1 1 d . . . H11 H 0.0953 0.9386 -0.0547 0.022 Uiso 1 1 calc R . . C12 C 0.0694(4) 0.9338(8) 0.0575(5) 0.024(2) Uani 1 1 d . . . H12A H 0.0833 1.0051 0.0867 0.029 Uiso 1 1 d R . . C13 C 0.0222(8) 0.7694(18) 0.0198(13) 0.019(2) Uani 0.50 1 d PU . . H13A H 0.0004 0.7000 0.0223 0.022 Uiso 0.50 1 d PR . . C13A C 0.0046(8) 0.8067(17) 0.0126(13) 0.018(2) Uani 0.50 1 d PU . . H13B H -0.0266 0.7562 0.0086 0.022 Uiso 0.50 1 d PR . . C14 C 0.0312(7) 0.8306(16) 0.1747(11) 0.019(2) Uani 0.50 1 d PU . . H14A H 0.0316 0.7477 0.1890 0.023 Uiso 0.50 1 d PR . . H14B H 0.0669 0.8730 0.2202 0.023 Uiso 0.50 1 d PR . . C14A C -0.0015(7) 0.8974(16) 0.1490(11) 0.018(2) Uani 0.50 1 d PU . . H14C H -0.0082 0.9803 0.1566 0.022 Uiso 0.50 1 d PR . . H14D H -0.0422 0.8576 0.1407 0.022 Uiso 0.50 1 d PR . . C15 C -0.0213(7) 0.8836(16) 0.1870(11) 0.019(2) Uani 0.50 1 d PU . . H15A H -0.0490 0.8574 0.1410 0.023 Uiso 0.50 1 d PR . . H15B H -0.0188 0.9687 0.1848 0.023 Uiso 0.50 1 d PR . . C15A C 0.0369(7) 0.8476(16) 0.2298(10) 0.018(2) Uani 0.50 1 d PU . . H15C H 0.0723 0.8787 0.2289 0.022 Uiso 0.50 1 d PR . . H15D H 0.0381 0.7625 0.2265 0.022 Uiso 0.50 1 d PR . . N1 N -0.1071(3) 0.4661(6) -0.1940(4) 0.0173(17) Uani 1 1 d . . . N2 N -0.1461(3) 0.3787(6) -0.0971(4) 0.0188(17) Uani 1 1 d . . . N3 N -0.2406(3) 0.4504(6) 0.2054(4) 0.0171(16) Uani 1 1 d . . . N4 N -0.2616(3) 0.3736(6) 0.3209(4) 0.0190(17) Uani 1 1 d . . . N5 N 0.0371(3) 0.8096(6) -0.0482(5) 0.0197(17) Uani 1 1 d . . . N6 N 0.0419(7) 0.8423(14) 0.0876(10) 0.017(2) Uani 0.50 1 d PU . . N6A N 0.0210(7) 0.8801(14) 0.0751(11) 0.0181(19) Uani 0.50 1 d PU . . 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 0.0234(6) 0.0205(6) 0.0167(6) -0.0058(4) 0.0057(5) -0.0048(5) Cu2 0.0179(6) 0.0192(6) 0.0170(6) 0.0006(4) 0.0042(5) -0.0044(5) Cu3 0.0243(6) 0.0209(6) 0.0138(6) 0.0025(4) 0.0023(5) 0.0002(5) I1 0.0171(3) 0.0172(3) 0.0217(3) -0.0007(2) 0.0075(3) 0.0027(2) I2 0.0191(3) 0.0222(3) 0.0128(3) 0.0042(2) 0.0003(2) 0.0006(2) I3 0.0177(3) 0.0246(3) 0.0211(3) 0.0001(2) 0.0040(3) 0.0030(3) C1 0.031(6) 0.018(5) 0.018(5) -0.003(4) -0.004(5) -0.015(4) C2 0.019(5) 0.027(5) 0.015(5) 0.000(4) 0.000(4) -0.001(4) C3 0.024(5) 0.019(5) 0.022(5) -0.002(4) 0.004(4) -0.004(4) C4 0.017(5) 0.032(5) 0.017(5) 0.006(4) 0.002(4) -0.002(4) C5 0.027(5) 0.009(4) 0.017(5) 0.006(4) -0.005(4) -0.002(4) C6 0.026(5) 0.017(5) 0.015(5) -0.001(4) 0.007(4) -0.006(4) C7 0.026(5) 0.031(6) 0.018(5) 0.007(4) 0.005(4) -0.010(4) C8 0.024(5) 0.022(5) 0.016(5) 0.003(4) 0.001(4) 0.003(4) C9 0.014(5) 0.024(5) 0.020(5) 0.003(4) 0.005(4) -0.001(4) C10 0.016(5) 0.026(5) 0.022(5) 0.006(4) 0.000(4) -0.001(4) C11 0.021(5) 0.016(5) 0.019(5) 0.004(4) 0.006(4) 0.003(4) C12 0.036(6) 0.028(5) 0.012(5) -0.012(4) 0.013(4) -0.024(5) C13 0.023(6) 0.019(5) 0.017(4) -0.005(4) 0.012(5) 0.006(4) C13A 0.023(6) 0.019(5) 0.016(4) -0.007(4) 0.012(5) 0.006(4) C14 0.023(5) 0.020(4) 0.016(4) -0.007(4) 0.010(4) 0.005(3) C14A 0.022(5) 0.020(4) 0.016(5) -0.008(4) 0.012(4) 0.006(4) C15 0.023(5) 0.020(5) 0.018(5) -0.006(4) 0.010(4) 0.004(4) C15A 0.023(5) 0.019(5) 0.016(5) -0.008(4) 0.011(5) 0.005(4) N1 0.014(4) 0.025(4) 0.013(4) -0.005(3) 0.002(3) -0.007(3) N2 0.020(4) 0.023(4) 0.014(4) 0.001(3) 0.006(3) 0.001(3) N3 0.020(4) 0.022(4) 0.009(4) 0.001(3) 0.004(3) -0.004(3) N4 0.013(4) 0.023(4) 0.021(4) 0.001(3) 0.003(3) 0.001(3) N5 0.016(4) 0.020(4) 0.023(4) -0.003(3) 0.003(3) 0.001(3) N6 0.021(5) 0.019(5) 0.014(4) -0.007(4) 0.011(4) 0.007(4) N6A 0.023(5) 0.019(5) 0.015(4) -0.007(4) 0.011(4) 0.005(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 2.013(7) . y Cu1 Cu2 2.6531(15) . y Cu1 I1 2.6586(12) 2_554 y Cu1 Cu2 2.6623(15) 2_554 y Cu1 I2 2.7137(12) . y Cu1 I1 2.7706(13) . y Cu1 Cu1 2.862(2) 2_554 y Cu2 N1 2.011(7) . y Cu2 I2 2.6071(12) 2_554 y Cu2 Cu1 2.6623(15) 2_554 ? Cu2 I1 2.6866(12) . y Cu2 Cu2 2.717(2) 2_554 y Cu2 I2 2.7639(12) . y Cu3 N4 1.938(7) . y Cu3 Cu3 2.450(2) 7_456 y Cu3 I3 2.5677(13) 7_456 y Cu3 I3 2.5753(12) . y I1 Cu1 2.6586(12) 2_554 ? I2 Cu2 2.6071(12) 2_554 ? I3 Cu3 2.5677(13) 7_456 ? C1 N1 1.326(11) . ? C1 N2 1.360(11) . ? C1 H1 0.9500 . ? C2 N1 1.358(11) . ? C2 C3 1.372(12) . ? C2 H2 0.9500 . ? C3 N2 1.361(11) . ? C3 H3 0.9500 . ? C4 N2 1.439(11) . ? C4 C5 1.533(12) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(12) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.520(12) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 N3 1.468(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.364(12) . ? C8 N3 1.391(11) . ? C8 H8 0.9500 . ? C9 N4 1.379(11) . ? C9 H9 0.9500 . ? C10 N4 1.318(11) . ? C10 N3 1.356(11) . ? C10 H10 0.9500 . ? C11 C12 1.336(12) . ? C11 N5 1.381(11) . ? C11 H11 0.9500 . ? C12 N6 1.378(18) . ? C12 N6A 1.434(19) . ? C12 H12A 0.9600 . ? C13 C13A 0.61(2) . ? C13 N5 1.30(2) . ? C13 N6 1.38(2) . ? C13 N6A 1.53(3) . ? C13 H13A 0.9600 . ? C13 H13B 1.2153 . ? C13A N6A 1.30(2) . ? C13A N5 1.39(2) . ? C13A N6 1.43(3) . ? C13A H13A 1.2174 . ? C13A H13B 0.9600 . ? C14 C15A 0.89(2) . ? C14 C14A 1.13(2) . ? C14 N6 1.48(2) . ? C14 C15 1.50(2) . ? C14 N6A 1.67(2) . ? C14 H14A 0.9600 . ? C14 H14B 1.1455 . ? C14 H15D 1.1203 . ? C14A C15 0.87(2) . ? C14A N6A 1.43(2) . ? C14A C15A 1.56(2) . ? C14A N6 1.72(2) . ? C14A H14C 0.9599 . ? C14A H14D 1.1010 . ? C14A H15A 1.2594 . ? C14A H15B 1.1239 . ? C15 C15A 1.52(2) 2 ? C15 C15A 1.54(2) . ? C15 H14C 1.2618 . ? C15 H14D 0.8746 . ? C15 H15A 0.9601 . ? C15 H15B 0.9599 . ? C15A C15 1.52(2) 2 ? C15A H14A 1.2946 . ? C15A H14B 0.8481 . ? C15A H15C 0.9601 . ? C15A H15D 0.9600 . ? N6 N6A 0.675(17) . ? 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 N5 Cu1 Cu2 137.1(2) . . ? N5 Cu1 I1 112.5(2) . 2_554 ? Cu2 Cu1 I1 110.32(5) . 2_554 ? N5 Cu1 Cu2 147.5(2) . 2_554 ? Cu2 Cu1 Cu2 61.49(5) . 2_554 ? I1 Cu1 Cu2 60.65(4) 2_554 2_554 ? N5 Cu1 I2 103.2(2) . . ? Cu2 Cu1 I2 61.98(4) . . ? I1 Cu1 I2 111.37(4) 2_554 . ? Cu2 Cu1 I2 58.01(3) 2_554 . ? N5 Cu1 I1 105.6(2) . . ? Cu2 Cu1 I1 59.34(3) . . ? I1 Cu1 I1 106.27(4) 2_554 . ? Cu2 Cu1 I1 106.71(4) 2_554 . ? I2 Cu1 I1 117.86(4) . . ? N5 Cu1 Cu1 151.0(2) . 2_554 ? Cu2 Cu1 Cu1 57.58(4) . 2_554 ? I1 Cu1 Cu1 60.11(4) 2_554 2_554 ? Cu2 Cu1 Cu1 57.27(4) 2_554 2_554 ? I2 Cu1 Cu1 105.54(3) . 2_554 ? I1 Cu1 Cu1 56.30(4) . 2_554 ? N1 Cu2 I2 110.7(2) . 2_554 ? N1 Cu2 Cu1 132.9(2) . . ? I2 Cu2 Cu1 115.16(5) 2_554 . ? N1 Cu2 Cu1 153.3(2) . 2_554 ? I2 Cu2 Cu1 61.98(4) 2_554 2_554 ? Cu1 Cu2 Cu1 65.16(5) . 2_554 ? N1 Cu2 I1 107.5(2) . . ? I2 Cu2 I1 113.90(4) 2_554 . ? Cu1 Cu2 I1 62.51(4) . . ? Cu1 Cu2 I1 59.61(4) 2_554 . ? N1 Cu2 Cu2 143.5(2) . 2_554 ? I2 Cu2 Cu2 62.50(4) 2_554 2_554 ? Cu1 Cu2 Cu2 59.42(4) . 2_554 ? Cu1 Cu2 Cu2 59.09(4) 2_554 2_554 ? I1 Cu2 Cu2 107.55(3) . 2_554 ? N1 Cu2 I2 96.9(2) . . ? I2 Cu2 I2 107.38(4) 2_554 . ? Cu1 Cu2 I2 60.09(3) . . ? Cu1 Cu2 I2 109.82(4) 2_554 . ? I1 Cu2 I2 119.05(4) . . ? Cu2 Cu2 I2 56.80(4) 2_554 . ? N4 Cu3 Cu3 174.3(2) . 7_456 ? N4 Cu3 I3 117.3(2) . 7_456 ? Cu3 Cu3 I3 61.71(5) 7_456 7_456 ? N4 Cu3 I3 119.2(2) . . ? Cu3 Cu3 I3 61.40(5) 7_456 . ? I3 Cu3 I3 123.11(4) 7_456 . ? Cu1 I1 Cu2 59.74(3) 2_554 . ? Cu1 I1 Cu1 63.59(4) 2_554 . ? Cu2 I1 Cu1 58.15(3) . . ? Cu2 I2 Cu1 60.01(3) 2_554 . ? Cu2 I2 Cu2 60.70(4) 2_554 . ? Cu1 I2 Cu2 57.93(3) . . ? Cu3 I3 Cu3 56.89(4) 7_456 . ? N1 C1 N2 111.9(7) . . ? N1 C1 H1 124.1 . . ? N2 C1 H1 124.1 . . ? N1 C2 C3 110.1(8) . . ? N1 C2 H2 125.0 . . ? C3 C2 H2 125.0 . . ? N2 C3 C2 106.5(8) . . ? N2 C3 H3 126.7 . . ? C2 C3 H3 126.7 . . ? N2 C4 C5 110.9(7) . . ? N2 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 113.3(7) . . ? C6 C5 H5A 108.9 . . ? C4 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? C4 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C7 C6 C5 112.4(7) . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6B 109.1 . . ? C5 C6 H6B 109.1 . . ? H6A C6 H6B 107.9 . . ? N3 C7 C6 109.8(7) . . ? N3 C7 H7A 109.7 . . ? C6 C7 H7A 109.7 . . ? N3 C7 H7B 109.7 . . ? C6 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C9 C8 N3 105.9(8) . . ? C9 C8 H8 127.1 . . ? N3 C8 H8 127.1 . . ? C8 C9 N4 109.4(8) . . ? C8 C9 H9 125.3 . . ? N4 C9 H9 125.3 . . ? N4 C10 N3 111.0(8) . . ? N4 C10 H10 124.5 . . ? N3 C10 H10 124.5 . . ? C12 C11 N5 110.1(8) . . ? C12 C11 H11 125.0 . . ? N5 C11 H11 125.0 . . ? C11 C12 N6 105.2(9) . . ? C11 C12 N6A 106.4(10) . . ? C11 C12 H12A 127.2 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.162 _refine_diff_density_min -0.936 _refine_diff_density_rms 0.219 _database_code_depnum_ccdc_archive 'CCDC 921018' ####################################################################### # # 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_global data_2-160K #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Cu3 I3 N6' _chemical_formula_weight 856.70 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.258(7) _cell_length_b 11.286(3) _cell_length_c 16.119(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.063(4) _cell_angle_gamma 90.00 _cell_volume 4510(2) _cell_formula_units_Z 8 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 1717 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 24.88 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3192 _exptl_absorpt_coefficient_mu 6.924 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5443 _exptl_absorpt_correction_T_max 0.6073 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8744 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0664 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3932 _reflns_number_gt 2775 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0611P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3932 _refine_ls_number_parameters 280 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1227 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.004 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.02055(5) 0.72508(11) -0.16041(8) 0.0320(3) Uani 1 1 d . . . Cu2 Cu -0.05128(5) 0.56568(11) -0.23536(7) 0.0275(3) Uani 1 1 d . . . Cu3 Cu -0.25462(5) 0.29218(11) 0.42877(8) 0.0304(3) Uani 1 1 d . . . I1 I -0.08369(3) 0.79343(6) -0.23406(4) 0.02832(19) Uani 1 1 d . . . I2 I 0.03707(3) 0.49354(6) -0.11672(4) 0.02731(19) Uani 1 1 d . . . I3 I -0.16247(3) 0.20802(6) 0.50033(4) 0.0332(2) Uani 1 1 d . . . C1 C -0.1162(4) 0.4702(9) -0.1162(7) 0.035(3) Uani 1 1 d . . . H1 H -0.1029 0.5301 -0.0782 0.042 Uiso 1 1 calc R . . C2 C -0.1339(4) 0.3664(9) -0.2270(6) 0.028(2) Uani 1 1 d . . . H2 H -0.1356 0.3392 -0.2819 0.034 Uiso 1 1 calc R . . C3 C -0.1582(4) 0.3132(9) -0.1695(7) 0.035(3) Uani 1 1 d . . . H3 H -0.1787 0.2442 -0.1771 0.041 Uiso 1 1 calc R . . C4 C -0.1658(4) 0.3616(10) -0.0180(7) 0.037(3) Uani 1 1 d . . . H4A H -0.1399 0.3947 0.0286 0.045 Uiso 1 1 calc R . . H4B H -0.1690 0.2775 -0.0080 0.045 Uiso 1 1 calc R . . C5 C -0.2196(5) 0.4206(9) -0.0230(6) 0.036(3) Uani 1 1 d . . . H5A H -0.2447 0.3896 -0.0713 0.043 Uiso 1 1 calc R . . H5B H -0.2158 0.5050 -0.0314 0.043 Uiso 1 1 calc R . . C6 C -0.2420(4) 0.3999(9) 0.0571(6) 0.033(3) Uani 1 1 d . . . H6A H -0.2797 0.4230 0.0463 0.040 Uiso 1 1 calc R . . H6B H -0.2403 0.3158 0.0698 0.040 Uiso 1 1 calc R . . C7 C -0.2132(5) 0.4661(10) 0.1335(7) 0.040(3) Uani 1 1 d . . . H7A H -0.1763 0.4377 0.1489 0.048 Uiso 1 1 calc R . . H7B H -0.2120 0.5499 0.1204 0.048 Uiso 1 1 calc R . . C8 C -0.2880(4) 0.5017(9) 0.2149(6) 0.029(2) Uani 1 1 d . . . H8 H -0.3078 0.5577 0.1796 0.035 Uiso 1 1 calc R . . C9 C -0.2996(4) 0.4550(9) 0.2865(6) 0.031(2) Uani 1 1 d . . . H9 H -0.3296 0.4751 0.3091 0.037 Uiso 1 1 calc R . . C10 C -0.2266(4) 0.3740(8) 0.2704(6) 0.022(2) Uani 1 1 d . . . H10 H -0.1956 0.3276 0.2781 0.027 Uiso 1 1 calc R . . C11 C 0.0718(4) 0.9002(9) -0.0210(6) 0.032(3) Uani 1 1 d . . . H11 H 0.0948 0.9341 -0.0530 0.039 Uiso 1 1 calc R . . C12 C 0.0691(5) 0.9337(10) 0.0577(7) 0.042(3) Uani 1 1 d . . . H12A H 0.0829 1.0050 0.0868 0.051 Uiso 1 1 d R . . C13 C 0.0209(10) 0.771(2) 0.0247(14) 0.028(3) Uani 0.50 1 d PU . . H13A H -0.0010 0.7015 0.0272 0.034 Uiso 0.50 1 d PR . . C13A C 0.0050(10) 0.805(2) 0.0074(14) 0.028(3) Uani 0.50 1 d PU . . H13B H -0.0262 0.7548 0.0034 0.034 Uiso 0.50 1 d PR . . C14 C 0.0312(9) 0.8290(19) 0.1783(12) 0.031(2) Uani 0.50 1 d PU . . H14A H 0.0315 0.7461 0.1927 0.037 Uiso 0.50 1 d PR . . H14B H 0.0668 0.8714 0.2239 0.037 Uiso 0.50 1 d PR . . C14A C -0.0028(9) 0.8998(18) 0.1484(12) 0.029(2) Uani 0.50 1 d PU . . H14C H -0.0095 0.9827 0.1561 0.035 Uiso 0.50 1 d PR . . H14D H -0.0435 0.8600 0.1402 0.035 Uiso 0.50 1 d PR . . C15 C -0.0205(9) 0.8800(18) 0.1860(12) 0.031(3) Uani 0.50 1 d PU . . H15A H -0.0483 0.8538 0.1399 0.037 Uiso 0.50 1 d PR . . H15B H -0.0181 0.9651 0.1837 0.037 Uiso 0.50 1 d PR . . C15A C 0.0346(9) 0.8467(18) 0.2313(12) 0.030(3) Uani 0.50 1 d PU . . H15C H 0.0700 0.8778 0.2304 0.036 Uiso 0.50 1 d PR . . H15D H 0.0358 0.7616 0.2280 0.036 Uiso 0.50 1 d PR . . N1 N -0.1067(3) 0.4645(7) -0.1946(5) 0.0256(19) Uani 1 1 d . . . N2 N -0.1469(4) 0.3804(8) -0.0977(5) 0.036(2) Uani 1 1 d . . . N3 N -0.2412(3) 0.4492(8) 0.2058(5) 0.030(2) Uani 1 1 d . . . N4 N -0.2610(3) 0.3735(7) 0.3215(5) 0.029(2) Uani 1 1 d . . . N5 N 0.0368(3) 0.8103(7) -0.0484(5) 0.032(2) Uani 1 1 d . . . N6 N 0.0404(8) 0.8443(17) 0.0898(11) 0.028(2) Uani 0.50 1 d PU . . N6A N 0.0208(8) 0.8775(16) 0.0704(11) 0.027(2) Uani 0.50 1 d PU . . 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 0.0378(8) 0.0313(7) 0.0280(7) -0.0088(5) 0.0093(6) -0.0073(6) Cu2 0.0282(7) 0.0288(7) 0.0267(7) 0.0013(5) 0.0086(6) -0.0072(5) Cu3 0.0384(8) 0.0320(7) 0.0204(7) 0.0031(5) 0.0048(6) 0.0009(6) I1 0.0270(4) 0.0256(4) 0.0349(4) -0.0015(3) 0.0123(3) 0.0037(3) I2 0.0285(4) 0.0313(4) 0.0206(4) 0.0063(3) 0.0008(3) -0.0005(3) I3 0.0280(4) 0.0395(4) 0.0325(4) 0.0016(3) 0.0069(3) 0.0044(3) C1 0.028(6) 0.035(6) 0.040(7) -0.007(5) 0.001(5) -0.015(5) C2 0.022(5) 0.031(6) 0.027(6) -0.004(5) -0.004(5) 0.001(5) C3 0.038(6) 0.030(6) 0.036(6) -0.007(5) 0.008(5) -0.017(5) C4 0.026(6) 0.051(7) 0.033(6) -0.006(5) -0.002(5) -0.013(5) C5 0.059(8) 0.020(5) 0.028(6) -0.001(4) 0.007(6) -0.007(5) C6 0.042(7) 0.025(6) 0.032(6) -0.004(4) 0.007(5) -0.004(5) C7 0.042(7) 0.048(7) 0.031(7) 0.006(5) 0.012(6) -0.009(6) C8 0.031(6) 0.039(6) 0.017(5) 0.005(5) 0.006(5) 0.012(5) C9 0.025(6) 0.039(6) 0.026(6) -0.004(5) 0.002(5) 0.007(5) C10 0.016(5) 0.032(6) 0.018(5) -0.001(4) 0.001(4) -0.008(4) C11 0.025(6) 0.047(7) 0.025(6) -0.004(5) 0.005(5) -0.010(5) C12 0.055(8) 0.038(7) 0.037(7) -0.007(5) 0.017(6) -0.019(6) C13 0.041(7) 0.028(6) 0.015(6) 0.012(5) 0.005(5) -0.011(5) C13A 0.041(7) 0.029(6) 0.015(6) 0.013(5) 0.004(5) -0.010(5) C14 0.043(6) 0.031(5) 0.016(5) 0.010(4) 0.003(5) -0.009(4) C14A 0.042(6) 0.029(5) 0.015(5) 0.011(4) 0.004(5) -0.009(4) C15 0.043(6) 0.031(5) 0.017(5) 0.011(5) 0.002(5) -0.008(4) C15A 0.043(6) 0.030(5) 0.015(5) 0.012(5) 0.003(5) -0.008(4) N1 0.031(5) 0.029(5) 0.018(5) -0.006(3) 0.010(4) -0.006(4) N2 0.036(5) 0.042(6) 0.030(5) -0.003(4) 0.006(4) -0.022(4) N3 0.026(5) 0.043(5) 0.021(5) 0.004(4) 0.007(4) -0.009(4) N4 0.028(5) 0.041(5) 0.019(4) -0.004(4) 0.005(4) 0.001(4) N5 0.032(5) 0.032(5) 0.032(5) -0.013(4) 0.008(4) -0.008(4) N6 0.041(6) 0.029(5) 0.015(5) 0.009(4) 0.004(5) -0.011(4) N6A 0.040(6) 0.027(5) 0.014(5) 0.012(4) 0.004(5) -0.010(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 Cu1 N5 2.017(8) . y Cu1 I1 2.6596(15) 2_554 y Cu1 Cu2 2.6733(18) . y Cu1 Cu2 2.6763(17) 2_554 y Cu1 I2 2.7178(15) . y Cu1 I1 2.7816(16) . y Cu1 Cu1 2.876(3) 2_554 y Cu2 N1 2.013(8) . y Cu2 I2 2.6087(15) 2_554 y Cu2 Cu1 2.6763(17) 2_554 ? Cu2 I1 2.6990(15) . y Cu2 Cu2 2.721(2) 2_554 y Cu2 I2 2.7680(14) . y Cu3 N4 1.937(8) . y Cu3 Cu3 2.455(2) 7_456 y Cu3 I3 2.5712(15) 7_456 y Cu3 I3 2.5729(15) . y I1 Cu1 2.6596(15) 2_554 ? I2 Cu2 2.6087(15) 2_554 ? I3 Cu3 2.5712(15) 7_456 ? C1 N1 1.332(13) . ? C1 N2 1.345(12) . ? C1 H1 0.9300 . ? C2 N1 1.354(12) . ? C2 C3 1.347(14) . ? C2 H2 0.9300 . ? C3 N2 1.367(12) . ? C3 H3 0.9300 . ? C4 N2 1.469(13) . ? C4 C5 1.501(14) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.526(14) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.504(14) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.487(13) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.350(14) . ? C8 N3 1.356(12) . ? C8 H8 0.9300 . ? C9 N4 1.381(12) . ? C9 H9 0.9300 . ? C10 N4 1.307(11) . ? C10 N3 1.340(12) . ? C10 H10 0.9300 . ? C11 C12 1.338(14) . ? C11 N5 1.364(12) . ? C11 H11 0.9300 . ? C12 N6 1.40(2) . ? C12 N6A 1.42(2) . ? C12 H12A 0.9637 . ? C13 C13A 0.59(3) . ? C13 N6 1.35(3) . ? C13 N5 1.39(2) . ? C13 N6A 1.41(3) . ? C13 H13A 0.9636 . ? C13 H13B 1.1863 . ? C13A N6A 1.30(3) . ? C13A N5 1.32(3) . ? C13A N6 1.52(3) . ? C13A H13A 1.2308 . ? C13A H13B 0.9641 . ? C14 C15A 0.87(2) . ? C14 C14A 1.20(3) . ? C14 C15 1.45(3) . ? C14 N6 1.50(3) . ? C14 N6A 1.80(3) . ? C14 H14A 0.9634 . ? C14 H14B 1.1511 . ? C14 H15C 1.2865 . ? C14 H15D 1.0942 . ? C14A C15 0.85(2) . ? C14A N6A 1.51(3) . ? C14A C15A 1.60(3) . ? C14A N6 1.69(3) . ? C14A H14C 0.9633 . ? C14A H14D 1.1060 . ? C14A H15A 1.2436 . ? C14A H15B 1.0498 . ? C15 C15A 1.49(3) 2 ? C15 C15A 1.49(3) . ? C15A C15A 1.95(4) 2 ? 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 N5 Cu1 I1 113.0(2) . 2_554 ? N5 Cu1 Cu2 136.8(2) . . ? I1 Cu1 Cu2 110.15(5) 2_554 . ? N5 Cu1 Cu2 148.1(3) . 2_554 ? I1 Cu1 Cu2 60.77(4) 2_554 2_554 ? Cu2 Cu1 Cu2 61.14(6) . 2_554 ? N5 Cu1 I2 103.4(3) . . ? I1 Cu1 I2 111.31(5) 2_554 . ? Cu2 Cu1 I2 61.78(4) . . ? Cu2 Cu1 I2 57.84(4) 2_554 . ? N5 Cu1 I1 105.2(3) . . ? I1 Cu1 I1 106.34(5) 2_554 . ? Cu2 Cu1 I1 59.27(4) . . ? Cu2 Cu1 I1 106.46(5) 2_554 . ? I2 Cu1 I1 117.58(5) . . ? N5 Cu1 Cu1 150.6(3) . 2_554 ? I1 Cu1 Cu1 60.18(5) 2_554 2_554 ? Cu2 Cu1 Cu1 57.54(4) . 2_554 ? Cu2 Cu1 Cu1 57.43(4) 2_554 2_554 ? I2 Cu1 Cu1 105.55(3) . 2_554 ? I1 Cu1 Cu1 56.06(4) . 2_554 ? N1 Cu2 I2 110.4(2) . 2_554 ? N1 Cu2 Cu1 133.5(2) . . ? I2 Cu2 Cu1 115.00(5) 2_554 . ? N1 Cu2 Cu1 152.9(2) . 2_554 ? I2 Cu2 Cu1 61.88(4) 2_554 2_554 ? Cu1 Cu2 Cu1 65.03(6) . 2_554 ? N1 Cu2 I1 107.9(2) . . ? I2 Cu2 I1 113.54(5) 2_554 . ? Cu1 Cu2 I1 62.36(4) . . ? Cu1 Cu2 I1 59.31(4) 2_554 . ? N1 Cu2 Cu2 143.3(2) . 2_554 ? I2 Cu2 Cu2 62.54(4) 2_554 2_554 ? Cu1 Cu2 Cu2 59.49(5) . 2_554 ? Cu1 Cu2 Cu2 59.37(4) 2_554 2_554 ? I1 Cu2 Cu2 107.56(3) . 2_554 ? N1 Cu2 I2 97.3(2) . . ? I2 Cu2 I2 107.80(5) 2_554 . ? Cu1 Cu2 I2 59.90(4) . . ? Cu1 Cu2 I2 109.81(5) 2_554 . ? I1 Cu2 I2 118.71(5) . . ? Cu2 Cu2 I2 56.75(4) 2_554 . ? N4 Cu3 Cu3 174.5(3) . 7_456 ? N4 Cu3 I3 117.5(3) . 7_456 ? Cu3 Cu3 I3 61.52(6) 7_456 7_456 ? N4 Cu3 I3 119.2(3) . . ? Cu3 Cu3 I3 61.45(5) 7_456 . ? I3 Cu3 I3 122.98(5) 7_456 . ? Cu1 I1 Cu2 59.92(4) 2_554 . ? Cu1 I1 Cu1 63.76(5) 2_554 . ? Cu2 I1 Cu1 58.37(4) . . ? Cu2 I2 Cu1 60.28(4) 2_554 . ? Cu2 I2 Cu2 60.71(5) 2_554 . ? Cu1 I2 Cu2 58.32(4) . . ? Cu3 I3 Cu3 57.02(5) 7_456 . ? N1 C1 N2 112.9(9) . . ? N1 C1 H1 123.6 . . ? N2 C1 H1 123.6 . . ? N1 C2 C3 111.3(9) . . ? N1 C2 H2 124.4 . . ? C3 C2 H2 124.4 . . ? C2 C3 N2 106.7(9) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? N2 C4 C5 109.4(9) . . ? N2 C4 H4A 109.8 . . ? C5 C4 H4A 109.8 . . ? N2 C4 H4B 109.8 . . ? C5 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C4 C5 C6 111.5(9) . . ? C4 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 114.6(9) . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6B 108.6 . . ? C5 C6 H6B 108.6 . . ? H6A C6 H6B 107.6 . . ? N3 C7 C6 110.4(9) . . ? N3 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? N3 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C9 C8 N3 105.1(9) . . ? C9 C8 H8 127.5 . . ? N3 C8 H8 127.5 . . ? C8 C9 N4 110.9(9) . . ? C8 C9 H9 124.6 . . ? N4 C9 H9 124.6 . . ? N4 C10 N3 112.0(9) . . ? N4 C10 H10 124.0 . . ? N3 C10 H10 124.0 . . ? C12 C11 N5 111.6(10) . . ? C12 C11 H11 124.2 . . ? N5 C11 H11 124.2 . . ? C11 C12 N6 105.8(12) . . ? C11 C12 N6A 102.3(12) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.017 _refine_diff_density_min -0.876 _refine_diff_density_rms 0.233 _database_code_depnum_ccdc_archive 'CCDC 921019' ####################################################################### # # 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_global data_2-220K #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Cu3 I3 N6' _chemical_formula_weight 856.70 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.367(11) _cell_length_b 11.290(5) _cell_length_c 16.143(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.920(7) _cell_angle_gamma 90.00 _cell_volume 4539(3) _cell_formula_units_Z 8 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 1401 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 23.11 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3192 _exptl_absorpt_coefficient_mu 6.879 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5462 _exptl_absorpt_correction_T_max 0.6091 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8835 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0796 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3951 _reflns_number_gt 2579 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0824P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3951 _refine_ls_number_parameters 280 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.0911 _refine_ls_R_factor_gt 0.0504 _refine_ls_wR_factor_ref 0.1681 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.02099(8) 0.72530(15) -0.16080(11) 0.0448(5) Uani 1 1 d . . . Cu2 Cu -0.05091(6) 0.56430(15) -0.23462(10) 0.0382(4) Uani 1 1 d . . . Cu3 Cu -0.25443(7) 0.29340(15) 0.42912(10) 0.0414(5) Uani 1 1 d . . . I1 I -0.08345(3) 0.79238(7) -0.23335(6) 0.0390(3) Uani 1 1 d . . . I2 I 0.03730(4) 0.49399(7) -0.11669(5) 0.0364(3) Uani 1 1 d . . . I3 I -0.16314(4) 0.20702(9) 0.50008(6) 0.0457(3) Uani 1 1 d . . . C1 C -0.1153(6) 0.4686(13) -0.1168(9) 0.046(4) Uani 1 1 d . . . H1 H -0.1014 0.5286 -0.0784 0.056 Uiso 1 1 calc R . . C2 C -0.1333(5) 0.3662(11) -0.2261(8) 0.038(3) Uani 1 1 d . . . H2 H -0.1343 0.3380 -0.2812 0.046 Uiso 1 1 calc R . . C3 C -0.1585(6) 0.3159(13) -0.1702(9) 0.047(4) Uani 1 1 d . . . H3 H -0.1806 0.2484 -0.1788 0.057 Uiso 1 1 calc R . . C4 C -0.1650(6) 0.3570(15) -0.0168(9) 0.055(4) Uani 1 1 d . . . H4A H -0.1703 0.2719 -0.0097 0.066 Uiso 1 1 calc R . . H4B H -0.1382 0.3852 0.0310 0.066 Uiso 1 1 calc R . . C5 C -0.2167(7) 0.4216(14) -0.0204(10) 0.066(5) Uani 1 1 d . . . H5A H -0.2421 0.3970 -0.0710 0.079 Uiso 1 1 calc R . . H5B H -0.2104 0.5068 -0.0249 0.079 Uiso 1 1 calc R . . C6 C -0.2413(7) 0.3976(15) 0.0582(9) 0.064(5) Uani 1 1 d . . . H6A H -0.2791 0.4217 0.0467 0.077 Uiso 1 1 calc R . . H6B H -0.2399 0.3124 0.0701 0.077 Uiso 1 1 calc R . . C7 C -0.2120(7) 0.4637(14) 0.1348(9) 0.056(4) Uani 1 1 d . . . H7A H -0.1752 0.4341 0.1505 0.067 Uiso 1 1 calc R . . H7B H -0.2105 0.5483 0.1219 0.067 Uiso 1 1 calc R . . C8 C -0.2869(7) 0.4996(13) 0.2142(9) 0.051(4) Uani 1 1 d . . . H8 H -0.3063 0.5563 0.1781 0.061 Uiso 1 1 calc R . . C9 C -0.2997(6) 0.4540(12) 0.2867(9) 0.045(4) Uani 1 1 d . . . H9 H -0.3302 0.4737 0.3090 0.054 Uiso 1 1 calc R . . C10 C -0.2250(6) 0.3736(12) 0.2697(8) 0.039(3) Uani 1 1 d . . . H10 H -0.1934 0.3279 0.2779 0.046 Uiso 1 1 calc R . . C11 C 0.0728(6) 0.9011(13) -0.0220(9) 0.050(4) Uani 1 1 d . . . H11 H 0.0967 0.9346 -0.0534 0.060 Uiso 1 1 calc R . . C12 C 0.0684(7) 0.9328(13) 0.0567(10) 0.056(4) Uani 1 1 d . . . H12A H 0.0822 1.0042 0.0859 0.067 Uiso 1 1 d R . . C13 C 0.0198(16) 0.774(4) 0.022(3) 0.048(4) Uani 0.50 1 d PU . . H13A H -0.0021 0.7048 0.0241 0.058 Uiso 0.50 1 d PR . . C13A C 0.0038(16) 0.802(3) 0.006(3) 0.048(4) Uani 0.50 1 d PU . . H13B H -0.0274 0.7515 0.0021 0.057 Uiso 0.50 1 d PR . . C14 C 0.0286(14) 0.828(3) 0.1804(19) 0.049(3) Uani 0.50 1 d PU . . H14A H 0.0290 0.7456 0.1947 0.059 Uiso 0.50 1 d PR . . H14B H 0.0643 0.8709 0.2259 0.059 Uiso 0.50 1 d PR . . C14A C -0.0057(13) 0.891(3) 0.1450(18) 0.048(3) Uani 0.50 1 d PU . . H14C H -0.0124 0.9740 0.1527 0.058 Uiso 0.50 1 d PR . . H14D H -0.0464 0.8513 0.1368 0.058 Uiso 0.50 1 d PR . . C15 C -0.0187(13) 0.881(3) 0.1928(19) 0.050(4) Uani 0.50 1 d PU . . H15A H -0.0464 0.8551 0.1467 0.060 Uiso 0.50 1 d PR . . H15B H -0.0162 0.9664 0.1905 0.060 Uiso 0.50 1 d PR . . C15A C 0.0330(13) 0.847(3) 0.2308(17) 0.048(4) Uani 0.50 1 d PU . . H15C H 0.0684 0.8783 0.2299 0.058 Uiso 0.50 1 d PR . . H15D H 0.0342 0.7620 0.2275 0.058 Uiso 0.50 1 d PR . . N1 N -0.1064(4) 0.4628(9) -0.1932(7) 0.034(3) Uani 1 1 d . . . N2 N -0.1463(5) 0.3801(10) -0.0984(7) 0.045(3) Uani 1 1 d . . . N3 N -0.2406(5) 0.4463(10) 0.2055(7) 0.042(3) Uani 1 1 d . . . N4 N -0.2604(4) 0.3745(9) 0.3215(6) 0.035(3) Uani 1 1 d . . . N5 N 0.0359(5) 0.8095(10) -0.0498(7) 0.043(3) Uani 1 1 d . . . N6 N 0.0363(12) 0.846(3) 0.084(2) 0.048(3) Uani 0.50 1 d PU . . N6A N 0.0167(12) 0.877(3) 0.071(2) 0.048(3) Uani 0.50 1 d PU . . 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 0.0556(11) 0.0417(10) 0.0393(10) -0.0111(8) 0.0149(9) -0.0110(9) Cu2 0.0375(9) 0.0427(10) 0.0365(10) 0.0001(7) 0.0121(8) -0.0096(8) Cu3 0.0528(11) 0.0438(10) 0.0274(9) 0.0049(7) 0.0073(8) 0.0000(9) I1 0.0374(5) 0.0345(5) 0.0488(6) -0.0031(4) 0.0178(4) 0.0049(4) I2 0.0399(5) 0.0403(5) 0.0274(5) 0.0081(4) 0.0022(4) -0.0012(4) I3 0.0391(5) 0.0540(6) 0.0452(6) 0.0035(4) 0.0111(5) 0.0072(5) C1 0.046(9) 0.058(10) 0.038(9) -0.008(7) 0.015(8) -0.031(7) C2 0.045(8) 0.037(8) 0.034(8) -0.006(6) 0.011(7) -0.003(7) C3 0.060(10) 0.044(9) 0.039(8) -0.006(7) 0.013(8) -0.020(8) C4 0.033(8) 0.077(11) 0.051(10) -0.001(8) 0.002(8) -0.014(8) C5 0.101(15) 0.037(9) 0.060(11) 0.005(8) 0.019(11) -0.003(9) C6 0.079(12) 0.062(11) 0.056(10) -0.003(8) 0.023(10) -0.025(9) C7 0.073(11) 0.060(10) 0.044(9) -0.003(8) 0.032(9) -0.028(9) C8 0.064(11) 0.045(9) 0.038(9) 0.006(7) -0.002(8) 0.011(8) C9 0.045(9) 0.045(9) 0.043(9) 0.000(7) 0.003(7) 0.006(7) C10 0.039(8) 0.042(8) 0.037(8) -0.003(7) 0.014(7) -0.012(6) C11 0.054(9) 0.059(10) 0.043(9) -0.007(7) 0.021(8) -0.013(8) C12 0.077(11) 0.039(9) 0.053(10) -0.016(8) 0.017(9) -0.014(8) C13 0.066(10) 0.047(9) 0.037(9) -0.002(7) 0.024(9) -0.008(7) C13A 0.066(10) 0.046(9) 0.036(9) -0.001(7) 0.024(9) -0.008(7) C14 0.067(9) 0.047(8) 0.038(9) -0.002(7) 0.024(8) -0.007(6) C14A 0.066(9) 0.047(8) 0.037(9) -0.001(7) 0.024(8) -0.007(6) C15 0.067(9) 0.048(8) 0.039(9) -0.003(7) 0.023(9) -0.007(6) C15A 0.067(9) 0.047(8) 0.037(9) -0.002(7) 0.024(9) -0.007(6) N1 0.039(6) 0.034(6) 0.033(7) -0.001(5) 0.016(5) -0.009(5) N2 0.044(7) 0.052(8) 0.045(7) -0.004(6) 0.025(6) -0.018(6) N3 0.056(8) 0.043(7) 0.027(6) 0.003(5) 0.011(6) -0.004(6) N4 0.034(6) 0.041(6) 0.033(6) 0.004(5) 0.009(5) 0.005(5) N5 0.053(7) 0.038(7) 0.042(7) -0.004(5) 0.014(6) -0.006(6) N6 0.066(9) 0.047(8) 0.037(8) -0.002(7) 0.025(8) -0.008(6) N6A 0.066(9) 0.046(8) 0.036(9) -0.001(7) 0.024(8) -0.007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 2.000(11) . ? Cu1 I1 2.651(2) 2_554 ? Cu1 Cu2 2.686(2) 2_554 ? Cu1 Cu2 2.688(2) . ? Cu1 I2 2.718(2) . ? Cu1 I1 2.791(2) . ? Cu1 Cu1 2.875(4) 2_554 ? Cu2 N1 2.024(10) . ? Cu2 I2 2.612(2) 2_554 ? Cu2 Cu1 2.686(2) 2_554 ? Cu2 I1 2.705(2) . ? Cu2 Cu2 2.721(3) 2_554 ? Cu2 I2 2.765(2) . ? Cu3 N4 1.945(10) . ? Cu3 Cu3 2.460(3) 7_456 ? Cu3 I3 2.566(2) 7_456 ? Cu3 I3 2.573(2) . ? I1 Cu1 2.651(2) 2_554 ? I2 Cu2 2.612(2) 2_554 ? I3 Cu3 2.566(2) 7_456 ? C1 N1 1.297(16) . ? C1 N2 1.339(16) . ? C1 H1 0.9400 . ? C2 C3 1.328(18) . ? C2 N1 1.342(15) . ? C2 H2 0.9400 . ? C3 N2 1.352(17) . ? C3 H3 0.9400 . ? C4 C5 1.49(2) . ? C4 N2 1.506(17) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C5 C6 1.54(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C7 1.51(2) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 N3 1.477(17) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 N3 1.350(18) . ? C8 C9 1.37(2) . ? C8 H8 0.9400 . ? C9 N4 1.379(16) . ? C9 H9 0.9400 . ? C10 N3 1.322(16) . ? C10 N4 1.337(16) . ? C10 H10 0.9400 . ? C11 C12 1.346(19) . ? C11 N5 1.411(17) . ? C11 H11 0.9400 . ? C12 N6 1.39(3) . ? C12 N6A 1.51(4) . ? C12 H12A 0.9650 . ? C13 N6A 1.42(6) . ? C13 N6 1.30(4) . ? C13 N5 1.35(4) . ? C13 H13A 0.9651 . ? C13 H13B 1.2050 . ? C13A N5 1.33(4) . ? C13A N6A 1.34(4) . ? C13A N6 1.46(6) . ? C13A H13A 1.1519 . ? C13A H13B 0.9670 . ? C14 C15A 0.83(3) . ? C14 C14A 1.18(4) . ? C14 C15 1.39(4) . ? C14 N6 1.62(4) . ? C14 N6A 1.82(4) . ? C14 H14A 0.9637 . ? C14 H14B 1.1556 . ? C14 H15C 1.2911 . ? C14 H15D 1.0589 . ? C14A C15 0.90(3) . ? C14A N6A 1.43(4) . ? C14A C15A 1.62(4) . ? C14A N6 1.66(4) . ? C14A H14C 0.9637 . ? C14A H14D 1.1104 . ? C14A H15A 1.1138 . ? C14A H15B 1.1872 . ? C15 C15A 1.39(4) . ? C15 C15A 1.40(4) 2 ? C15 C15 1.91(6) 2 ? C15 H14C 1.2554 . ? C15 H14D 1.0895 . ? C15 H15A 0.9684 . ? C15 H15B 0.9636 . ? C15A C15 1.40(4) 2 ? C15A C15A 1.89(6) 2 ? C15A H14A 1.2817 . ? C15A H14B 0.8561 . ? C15A H15C 0.9678 . ? C15A H15D 0.9637 . ? N6 N6A 0.61(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Cu1 I1 114.0(3) . 2_554 ? N5 Cu1 Cu2 148.9(4) . 2_554 ? I1 Cu1 Cu2 60.90(6) 2_554 2_554 ? N5 Cu1 Cu2 135.7(3) . . ? I1 Cu1 Cu2 110.21(7) 2_554 . ? Cu2 Cu1 Cu2 60.83(8) 2_554 . ? N5 Cu1 I2 103.2(3) . . ? I1 Cu1 I2 111.31(7) 2_554 . ? Cu2 Cu1 I2 57.82(6) 2_554 . ? Cu2 Cu1 I2 61.53(6) . . ? N5 Cu1 I1 104.5(3) . . ? I1 Cu1 I1 106.72(7) 2_554 . ? Cu2 Cu1 I1 106.18(7) 2_554 . ? Cu2 Cu1 I1 59.14(6) . . ? I2 Cu1 I1 117.14(7) . . ? N5 Cu1 Cu1 150.3(3) . 2_554 ? I1 Cu1 Cu1 60.50(7) 2_554 2_554 ? Cu2 Cu1 Cu1 57.69(6) 2_554 2_554 ? Cu2 Cu1 Cu1 57.63(6) . 2_554 ? I2 Cu1 Cu1 105.76(4) . 2_554 ? I1 Cu1 Cu1 55.78(6) . 2_554 ? N1 Cu2 I2 110.6(3) . 2_554 ? N1 Cu2 Cu1 152.6(3) . 2_554 ? I2 Cu2 Cu1 61.70(6) 2_554 2_554 ? N1 Cu2 Cu1 133.8(3) . . ? I2 Cu2 Cu1 114.59(7) 2_554 . ? Cu1 Cu2 Cu1 64.68(8) 2_554 . ? N1 Cu2 I1 107.7(3) . . ? I2 Cu2 I1 112.94(6) 2_554 . ? Cu1 Cu2 I1 58.91(6) 2_554 . ? Cu1 Cu2 I1 62.32(6) . . ? N1 Cu2 Cu2 143.5(3) . 2_554 ? I2 Cu2 Cu2 62.43(6) 2_554 2_554 ? Cu1 Cu2 Cu2 59.62(6) 2_554 2_554 ? Cu1 Cu2 Cu2 59.55(6) . 2_554 ? I1 Cu2 Cu2 107.63(4) . 2_554 ? N1 Cu2 I2 97.6(3) . . ? I2 Cu2 I2 108.35(7) 2_554 . ? Cu1 Cu2 I2 109.80(7) 2_554 . ? Cu1 Cu2 I2 59.76(6) . . ? I1 Cu2 I2 118.44(6) . . ? N4 Cu3 Cu3 175.4(3) . 7_456 ? N4 Cu3 I3 117.8(3) . 7_456 ? Cu3 Cu3 I3 61.54(8) 7_456 7_456 ? N4 Cu3 I3 119.2(3) . . ? Cu3 Cu3 I3 61.25(7) 7_456 . ? I3 Cu3 I3 122.79(7) 7_456 . ? Cu1 I1 Cu2 60.18(5) 2_554 . ? Cu1 I1 Cu1 63.72(7) 2_554 . ? Cu2 I1 Cu1 58.54(5) . . ? Cu2 I2 Cu1 60.49(5) 2_554 . ? Cu2 I2 Cu2 60.71(6) 2_554 . ? Cu1 I2 Cu2 58.71(5) . . ? Cu3 I3 Cu3 57.21(7) 7_456 . ? N1 C1 N2 112.9(12) . . ? N1 C1 H1 123.6 . . ? N2 C1 H1 123.6 . . ? C3 C2 N1 110.6(12) . . ? C3 C2 H2 124.7 . . ? N1 C2 H2 124.7 . . ? C2 C3 N2 107.0(12) . . ? C2 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? C5 C4 N2 107.5(12) . . ? H4A C4 H4B 108.5 . . ? C4 C5 C6 111.8(14) . . ? H5A C5 H5B 107.9 . . ? C7 C6 C5 111.9(13) . . ? H6A C6 H6B 107.9 . . ? N3 C7 C6 109.2(12) . . ? H7A C7 H7B 108.3 . . ? N3 C8 C9 105.8(12) . . ? N3 C8 H8 127.1 . . ? C9 C8 H8 127.1 . . ? C8 C9 N4 108.8(13) . . ? C8 C9 H9 125.6 . . ? N4 C9 H9 125.6 . . ? N3 C10 N4 110.3(13) . . ? N3 C10 H10 124.8 . . ? N4 C10 H10 124.8 . . ? C12 C11 N5 109.0(13) . . ? C12 C11 H11 125.5 . . ? N5 C11 H11 125.5 . . ? N6 C12 C11 105.7(18) . . ? N6 C12 N6A 24.0(14) . . ? C11 C12 N6A 105.1(18) . . ? N6 C12 H12A 127.6 . . ? C11 C12 H12A 126.5 . . ? N6A C12 H12A 121.4 . . ? N6A C13 N6 25.6(19) . . ? N6A C13 N5 107(3) . . ? N6 C13 N5 112(3) . . ? N5 C13A N6A 114(3) . . ? N5 C13A N6 104(3) . . ? C15A C14 C14A 106(5) . . ? C15A C14 C15 73(4) . . ? C14A C14 C15 40.0(19) . . ? C15A C14 N6 154(4) . . ? C14A C14 N6 71(2) . . ? C15 C14 N6 111(3) . . ? C15A C14 N6A 148(4) . . ? C14A C14 N6A 52(2) . . ? C15 C14 N6A 91(3) . . ? N6 C14 N6A 19.3(14) . . ? C15 C14A C14 82(3) . . ? C15 C14A N6A 167(4) . . ? C14 C14A N6A 88(3) . . ? C15 C14A C15A 59(3) . . ? N6A C14A C15A 114(3) . . ? C15 C14A N6 148(4) . . ? C14 C14A N6 67(2) . . ? C15A C14A N6 93(2) . . ? C14A C15 C15A 87(3) . . ? C14A C15 C14 58(3) . . ? C14A C15 C15A 169(4) . 2 ? C15A C15 C15A 85(3) . 2 ? C14 C15 C15A 112(3) . 2 ? C14A C15 C15 129(4) . 2 ? C14 C15 C15 82(3) . 2 ? C14 C15A C15 72(4) . . ? C14 C15A C15 158(5) . 2 ? C15 C15A C15 86(3) . 2 ? C14A C15A C15A 81(2) . 2 ? C1 N1 C2 104.5(11) . . ? C1 N1 Cu2 122.9(9) . . ? C2 N1 Cu2 131.5(9) . . ? C1 N2 C3 105.0(11) . . ? C1 N2 C4 128.3(12) . . ? C3 N2 C4 126.7(12) . . ? C10 N3 C8 109.4(12) . . ? C10 N3 C7 124.8(13) . . ? C8 N3 C7 125.8(13) . . ? C10 N4 C9 105.7(11) . . ? C10 N4 Cu3 127.4(9) . . ? C9 N4 Cu3 126.7(9) . . ? C13A N5 C11 107(2) . . ? C11 N5 C13 104(2) . . ? C13A N5 Cu1 123(2) . . ? C11 N5 Cu1 129.4(9) . . ? C13 N5 Cu1 126(2) . . ? N6A N6 C13 88(6) . . ? N6A N6 C12 88(6) . . ? C13 N6 C12 108(3) . . ? N6A N6 C13A 67(5) . . ? C12 N6 C13A 104(3) . . ? N6A N6 C14 100(6) . . ? C13 N6 C14 126(3) . . ? C12 N6 C14 125(3) . . ? C13A N6 C14 130(3) . . ? N6A N6 C14A 58(5) . . ? C13 N6 C14A 120(3) . . ? C12 N6 C14A 117(2) . . ? C13A N6 C14A 107(3) . . ? C14 N6 C14A 42.2(16) . . ? N6 N6A C13 67(5) . . ? N6 N6A C13A 89(6) . . ? N6 N6A C14A 101(6) . . ? C13 N6A C14A 129(3) . . ? C13A N6A C14A 130(3) . . ? N6 N6A C12 68(5) . . ? C13 N6A C12 97(3) . . ? C13A N6A C12 104(3) . . ? C14A N6A C12 125(3) . . ? N6 N6A C14 61(5) . . ? C13 N6A C14 106(2) . . ? C13A N6A C14 122(2) . . ? C14A N6A C14 40.3(17) . . ? C12 N6A C14 106(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.103 _refine_diff_density_min -1.220 _refine_diff_density_rms 0.304 _database_code_depnum_ccdc_archive 'CCDC 921020' ####################################################################### # # 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_global data_2-298K #TrackingRef 'web_deposit_cif_file_0_disun_1358734077.1 and 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 Cu3 I3 N6' _chemical_formula_weight 856.70 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.640(7) _cell_length_b 11.421(3) _cell_length_c 16.219(5) _cell_angle_alpha 90.00 _cell_angle_beta 100.823(5) _cell_angle_gamma 90.00 _cell_volume 4665(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 816 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 19.90 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3192 _exptl_absorpt_coefficient_mu 6.694 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5541 _exptl_absorpt_correction_T_max 0.6165 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10182 _diffrn_reflns_av_R_equivalents 0.0391 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4117 _reflns_number_gt 2748 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4117 _refine_ls_number_parameters 280 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1688 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.02123(7) 0.72605(13) -0.16118(9) 0.0648(5) Uani 1 1 d . . . Cu2 Cu -0.05028(5) 0.56306(12) -0.23424(9) 0.0553(4) Uani 1 1 d . . . Cu3 Cu -0.25411(6) 0.29468(12) 0.42941(9) 0.0605(4) Uani 1 1 d . . . I1 I -0.08321(3) 0.79076(6) -0.23274(5) 0.0557(3) Uani 1 1 d . . . I2 I 0.03734(3) 0.49592(6) -0.11636(4) 0.0516(3) Uani 1 1 d . . . I3 I -0.16393(3) 0.20704(7) 0.50002(6) 0.0674(3) Uani 1 1 d . . . C1 C -0.1150(5) 0.4708(12) -0.1172(8) 0.073(4) Uani 1 1 d . . . H1 H -0.1020 0.5299 -0.0795 0.088 Uiso 1 1 calc R . . C2 C -0.1327(4) 0.3660(10) -0.2273(7) 0.059(3) Uani 1 1 d . . . H2 H -0.1335 0.3386 -0.2815 0.071 Uiso 1 1 calc R . . C3 C -0.1581(5) 0.3185(12) -0.1711(9) 0.073(4) Uani 1 1 d . . . H3 H -0.1798 0.2526 -0.1790 0.087 Uiso 1 1 calc R . . C4 C -0.1649(6) 0.3568(15) -0.0167(9) 0.085(4) Uani 1 1 d . . . H4A H -0.1706 0.2734 -0.0112 0.102 Uiso 1 1 calc R . . H4B H -0.1384 0.3824 0.0306 0.102 Uiso 1 1 calc R . . C5 C -0.2144(8) 0.4207(13) -0.0191(11) 0.111(6) Uani 1 1 d . . . H5A H -0.2406 0.3964 -0.0672 0.134 Uiso 1 1 calc R . . H5B H -0.2085 0.5042 -0.0232 0.134 Uiso 1 1 calc R . . C6 C -0.2342(8) 0.3912(18) 0.0654(11) 0.133(8) Uani 1 1 d . . . H6A H -0.2725 0.3996 0.0555 0.160 Uiso 1 1 calc R . . H6B H -0.2260 0.3098 0.0793 0.160 Uiso 1 1 calc R . . C7 C -0.2126(6) 0.4593(13) 0.1342(8) 0.081(4) Uani 1 1 d . . . H7A H -0.2139 0.5409 0.1172 0.098 Uiso 1 1 calc R . . H7B H -0.1756 0.4381 0.1525 0.098 Uiso 1 1 calc R . . C8 C -0.2878(6) 0.4956(10) 0.2164(8) 0.066(3) Uani 1 1 d . . . H8 H -0.3078 0.5487 0.1800 0.080 Uiso 1 1 calc R . . C9 C -0.3003(4) 0.4544(11) 0.2880(7) 0.057(3) Uani 1 1 d . . . H9 H -0.3299 0.4753 0.3103 0.069 Uiso 1 1 calc R . . C10 C -0.2267(5) 0.3730(11) 0.2704(7) 0.058(3) Uani 1 1 d . . . H10 H -0.1966 0.3259 0.2783 0.070 Uiso 1 1 calc R . . C11 C 0.0712(5) 0.8986(9) -0.0202(7) 0.057(3) Uani 1 1 d . . . H11 H 0.0950 0.9316 -0.0503 0.069 Uiso 1 1 calc R . . C12 C 0.0672(6) 0.9299(12) 0.0578(9) 0.081(4) Uani 1 1 d . . . H12A H 0.0810 1.0012 0.0870 0.098 Uiso 1 1 d R . . C13 C 0.0168(16) 0.787(4) 0.022(2) 0.067(5) Uani 0.50 1 d PU . . H13A H -0.0050 0.7179 0.0242 0.080 Uiso 0.50 1 d PR . . C13A C 0.0020(16) 0.803(4) -0.0008(19) 0.066(5) Uani 0.50 1 d PU . . H13B H -0.0292 0.7522 -0.0047 0.080 Uiso 0.50 1 d PR . . C14 C 0.0264(13) 0.832(3) 0.1816(17) 0.076(4) Uani 0.50 1 d PU . . H14A H 0.0268 0.7489 0.1959 0.091 Uiso 0.50 1 d PR . . H14B H 0.0621 0.8742 0.2271 0.091 Uiso 0.50 1 d PR . . C14A C -0.0062(12) 0.885(3) 0.1374(15) 0.072(4) Uani 0.50 1 d PU . . H14C H -0.0129 0.9684 0.1450 0.086 Uiso 0.50 1 d PR . . H14D H -0.0469 0.8457 0.1291 0.086 Uiso 0.50 1 d PR . . C15 C -0.0132(13) 0.885(3) 0.1864(18) 0.080(5) Uani 0.50 1 d PU . . H15A H -0.0409 0.8591 0.1403 0.096 Uiso 0.50 1 d PR . . H15B H -0.0107 0.9704 0.1842 0.096 Uiso 0.50 1 d PR . . C15A C 0.0296(12) 0.845(3) 0.2284(15) 0.073(4) Uani 0.50 1 d PU . . H15C H 0.0650 0.8758 0.2275 0.088 Uiso 0.50 1 d PR . . H15D H 0.0308 0.7595 0.2251 0.088 Uiso 0.50 1 d PR . . N1 N -0.1050(3) 0.4622(8) -0.1920(6) 0.050(2) Uani 1 1 d . . . N2 N -0.1465(4) 0.3837(10) -0.1007(6) 0.070(3) Uani 1 1 d . . . N3 N -0.2407(4) 0.4462(9) 0.2057(6) 0.062(3) Uani 1 1 d . . . N4 N -0.2614(4) 0.3759(9) 0.3225(6) 0.057(2) Uani 1 1 d . . . N5 N 0.0357(4) 0.8117(8) -0.0502(6) 0.061(3) Uani 1 1 d . . . N6 N 0.0366(11) 0.850(3) 0.0838(17) 0.070(4) Uani 0.50 1 d PU . . N6A N 0.0157(11) 0.876(3) 0.0651(16) 0.067(4) Uani 0.50 1 d PU . . 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 0.0827(11) 0.0625(9) 0.0535(9) -0.0160(7) 0.0238(8) -0.0141(8) Cu2 0.0595(9) 0.0607(9) 0.0500(8) 0.0001(7) 0.0212(7) -0.0149(7) Cu3 0.0805(11) 0.0637(9) 0.0386(8) 0.0067(6) 0.0139(7) -0.0013(8) I1 0.0567(5) 0.0494(4) 0.0670(5) -0.0043(3) 0.0274(4) 0.0072(3) I2 0.0586(5) 0.0581(5) 0.0368(4) 0.0103(3) 0.0056(3) -0.0015(4) I3 0.0612(5) 0.0784(6) 0.0653(6) 0.0051(4) 0.0190(4) 0.0093(4) C1 0.081(9) 0.089(9) 0.050(8) -0.005(6) 0.015(7) -0.047(8) C2 0.068(8) 0.057(7) 0.054(7) -0.007(6) 0.016(6) -0.016(6) C3 0.072(8) 0.079(9) 0.069(9) -0.010(7) 0.021(7) -0.027(7) C4 0.071(9) 0.103(11) 0.082(10) 0.014(9) 0.015(8) -0.016(9) C5 0.179(19) 0.060(9) 0.100(13) 0.002(9) 0.042(13) -0.012(11) C6 0.187(18) 0.150(16) 0.095(12) -0.050(12) 0.108(13) -0.079(14) C7 0.104(11) 0.102(10) 0.044(7) -0.006(7) 0.030(7) -0.057(9) C8 0.083(9) 0.060(8) 0.055(8) 0.009(6) 0.010(7) 0.007(7) C9 0.050(7) 0.081(8) 0.044(7) -0.006(6) 0.015(6) 0.002(6) C10 0.070(8) 0.061(7) 0.044(7) -0.005(6) 0.011(6) -0.006(6) C11 0.070(8) 0.048(6) 0.059(8) -0.011(5) 0.022(6) -0.025(6) C12 0.113(11) 0.059(8) 0.079(10) -0.019(7) 0.037(9) -0.021(8) C13 0.098(12) 0.072(9) 0.033(11) 0.000(8) 0.020(9) -0.012(9) C13A 0.100(12) 0.071(9) 0.031(10) -0.003(8) 0.021(9) -0.012(9) C14 0.106(11) 0.081(9) 0.043(9) 0.000(8) 0.020(9) -0.005(8) C14A 0.103(11) 0.080(8) 0.037(9) -0.002(7) 0.023(8) -0.002(7) C15 0.110(11) 0.084(9) 0.048(9) -0.002(9) 0.017(10) -0.003(8) C15A 0.105(11) 0.080(9) 0.039(10) -0.006(8) 0.021(9) -0.004(8) N1 0.049(5) 0.062(6) 0.043(5) 0.010(4) 0.022(4) -0.004(4) N2 0.076(7) 0.089(8) 0.050(6) -0.007(6) 0.025(5) -0.034(6) N3 0.079(7) 0.073(7) 0.036(5) -0.002(5) 0.015(5) -0.014(6) N4 0.059(6) 0.071(6) 0.040(5) 0.008(5) 0.008(5) 0.005(5) N5 0.088(7) 0.051(6) 0.049(6) -0.001(5) 0.029(5) 0.000(5) N6 0.102(11) 0.075(9) 0.036(9) -0.003(7) 0.022(8) -0.009(8) N6A 0.099(12) 0.074(9) 0.032(9) -0.003(7) 0.018(8) -0.005(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N5 2.021(9) . y Cu1 I1 2.6568(18) 2_554 y Cu1 Cu2 2.715(2) 2_554 y Cu1 Cu2 2.723(2) . y Cu1 I2 2.7374(18) . y Cu1 I1 2.8101(19) . y Cu1 Cu1 2.882(3) 2_554 y Cu2 N1 2.031(8) . y Cu2 I2 2.6214(17) 2_554 y Cu2 Cu1 2.715(2) 2_554 ? Cu2 Cu2 2.721(3) 2_554 y Cu2 I1 2.7356(17) . y Cu2 I2 2.7707(16) . y Cu3 N4 1.945(9) . y Cu3 Cu3 2.480(3) 7_456 y Cu3 I3 2.5749(19) 7_456 y Cu3 I3 2.5816(18) . y I1 Cu1 2.6568(18) 2_554 ? I2 Cu2 2.6214(17) 2_554 ? I3 Cu3 2.5749(19) 7_456 ? C1 N1 1.290(15) . ? C1 N2 1.340(15) . ? C1 H1 0.9300 . ? C2 C3 1.331(16) . ? C2 N1 1.373(13) . ? C2 H2 0.9300 . ? C3 N2 1.349(16) . ? C3 H3 0.9300 . ? C4 C5 1.46(2) . ? C4 N2 1.556(17) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.58(2) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.39(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 N3 1.483(15) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.347(17) . ? C8 N3 1.373(16) . ? C8 H8 0.9300 . ? C9 N4 1.379(14) . ? C9 H9 0.9300 . ? C10 N3 1.337(14) . ? C10 N4 1.337(14) . ? C10 H10 0.9300 . ? C11 C12 1.336(17) . ? C11 N5 1.372(13) . ? C11 H11 0.9300 . ? C12 N6 1.32(3) . ? C12 N6A 1.48(3) . ? C12 H12A 0.9751 . ? C13 N6A 1.23(6) . ? C13 N6 1.27(4) . ? C13 N5 1.37(4) . ? C13 H13A 0.9760 . ? C13 H13B 1.2419 . ? C13A N5 1.29(4) . ? C13A N6A 1.35(4) . ? C13A N6 1.58(5) . ? C13A H13A 1.0782 . ? C13A H13B 0.9779 . ? C14 C15A 0.76(3) . ? C14 C14A 1.17(4) . ? C14 C15 1.20(4) . ? C14 N6 1.67(4) . ? C14 N6A 1.92(4) . ? C14 H14A 0.9745 . ? C14 H14B 1.1670 . ? C14 H15C 1.2283 . ? C14 H15D 1.0778 . ? C14A C15 0.85(3) . ? C14A N6A 1.40(4) . ? C14A N6 1.58(4) . ? C14A C15A 1.65(4) . ? C14A H14C 0.9746 . ? C14A H14D 1.1227 . ? C14A H15A 0.9486 . ? C14A H15B 1.2508 . ? C15 C15A 1.27(4) . ? C15 C15A 1.59(4) 2 ? C15 H14C 1.1625 . ? C15 H14D 1.2311 . ? C15 H15A 0.9770 . ? C15 H15B 0.9748 . ? C15A C15 1.59(4) 2 ? C15A C15A 1.79(6) 2 ? C15A H14A 1.2110 . ? C15A H14B 0.9030 . ? C15A H15C 0.9783 . ? C15A H15D 0.9748 . ? N6 N6A 0.63(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N5 Cu1 I1 114.2(3) . 2_554 ? N5 Cu1 Cu2 149.6(3) . 2_554 ? I1 Cu1 Cu2 61.22(5) 2_554 2_554 ? N5 Cu1 Cu2 135.6(3) . . ? I1 Cu1 Cu2 110.13(6) 2_554 . ? Cu2 Cu1 Cu2 60.05(7) 2_554 . ? N5 Cu1 I2 103.6(3) . . ? I1 Cu1 I2 111.12(6) 2_554 . ? Cu2 Cu1 I2 57.47(5) 2_554 . ? Cu2 Cu1 I2 60.98(5) . . ? N5 Cu1 I1 104.0(3) . . ? I1 Cu1 I1 107.39(6) 2_554 . ? Cu2 Cu1 I1 105.91(6) 2_554 . ? Cu2 Cu1 I1 59.24(5) . . ? I2 Cu1 I1 116.54(6) . . ? N5 Cu1 Cu1 149.5(3) . 2_554 ? I1 Cu1 Cu1 60.81(6) 2_554 2_554 ? Cu2 Cu1 Cu1 58.13(5) 2_554 2_554 ? Cu2 Cu1 Cu1 57.86(5) . 2_554 ? I2 Cu1 Cu1 105.98(3) . 2_554 ? I1 Cu1 Cu1 55.63(5) . 2_554 ? N1 Cu2 I2 111.2(3) . 2_554 ? N1 Cu2 Cu1 152.5(3) . 2_554 ? I2 Cu2 Cu1 61.69(5) 2_554 2_554 ? N1 Cu2 Cu2 143.4(3) . 2_554 ? I2 Cu2 Cu2 62.45(5) 2_554 2_554 ? Cu1 Cu2 Cu2 60.12(5) 2_554 2_554 ? N1 Cu2 Cu1 133.8(3) . . ? I2 Cu2 Cu1 114.23(6) 2_554 . ? Cu1 Cu2 Cu1 64.02(7) 2_554 . ? Cu2 Cu2 Cu1 59.83(5) 2_554 . ? N1 Cu2 I1 107.6(3) . . ? I2 Cu2 I1 112.28(5) 2_554 . ? Cu1 Cu2 I1 58.34(5) 2_554 . ? Cu2 Cu2 I1 107.85(3) 2_554 . ? Cu1 Cu2 I1 61.97(5) . . ? N1 Cu2 I2 97.6(3) . . ? I2 Cu2 I2 109.27(6) 2_554 . ? Cu1 Cu2 I2 109.81(6) 2_554 . ? Cu2 Cu2 I2 57.01(5) 2_554 . ? Cu1 Cu2 I2 59.77(5) . . ? I1 Cu2 I2 117.94(5) . . ? N4 Cu3 Cu3 175.7(3) . 7_456 ? N4 Cu3 I3 116.8(3) . 7_456 ? Cu3 Cu3 I3 61.39(7) 7_456 7_456 ? N4 Cu3 I3 120.6(3) . . ? Cu3 Cu3 I3 61.12(7) 7_456 . ? I3 Cu3 I3 122.52(6) 7_456 . ? Cu1 I1 Cu2 60.44(4) 2_554 . ? Cu1 I1 Cu1 63.57(6) 2_554 . ? Cu2 I1 Cu1 58.80(4) . . ? Cu2 I2 Cu1 60.84(4) 2_554 . ? Cu2 I2 Cu2 60.54(5) 2_554 . ? Cu1 I2 Cu2 59.25(4) . . ? Cu3 I3 Cu3 57.48(6) 7_456 . ? N1 C1 N2 111.4(11) . . ? N1 C1 H1 124.3 . . ? N2 C1 H1 124.3 . . ? C3 C2 N1 108.8(11) . . ? C3 C2 H2 125.6 . . ? N1 C2 H2 125.6 . . ? C2 C3 N2 107.2(11) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? C5 C4 N2 106.5(12) . . ? C5 C4 H4A 110.4 . . ? N2 C4 H4A 110.4 . . ? C5 C4 H4B 110.4 . . ? N2 C4 H4B 110.4 . . ? H4A C4 H4B 108.6 . . ? C4 C5 C6 106.8(15) . . ? C4 C5 H5A 110.4 . . ? C6 C5 H5A 110.4 . . ? C4 C5 H5B 110.4 . . ? C6 C5 H5B 110.4 . . ? H5A C5 H5B 108.6 . . ? C7 C6 C5 115.6(13) . . ? C7 C6 H6A 108.4 . . ? C5 C6 H6A 108.4 . . ? C7 C6 H6B 108.4 . . ? C5 C6 H6B 108.4 . . ? H6A C6 H6B 107.4 . . ? C6 C7 N3 113.2(11) . . ? C6 C7 H7A 108.9 . . ? N3 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? N3 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? C9 C8 N3 108.9(11) . . ? C9 C8 H8 125.6 . . ? N3 C8 H8 125.6 . . ? C8 C9 N4 107.8(11) . . ? C8 C9 H9 126.1 . . ? N4 C9 H9 126.1 . . ? N3 C10 N4 111.6(11) . . ? N3 C10 H10 124.2 . . ? N4 C10 H10 124.2 . . ? C12 C11 N5 111.5(11) . . ? C12 C11 H11 124.3 . . ? N5 C11 H11 124.3 . . ? N6 C12 C11 105.9(16) . . ? N6 C12 N6A 25.3(14) . . ? C11 C12 N6A 101.0(15) . . ? N6 C12 H12A 127.2 . . ? C11 C12 H12A 126.7 . . ? N6A C12 H12A 124.0 . . ? N6A C13 N6 29.4(18) . . ? N6A C13 N5 112(4) . . ? N6 C13 N5 114(3) . . ? N6A C13 H13A 124.4 . . ? N6 C13 H13A 125.2 . . ? N5 C13 H13A 119.9 . . ? N6A C13 H13B 109.7 . . ? N6 C13 H13B 132.2 . . ? N5 C13 H13B 103.7 . . ? H13A C13 H13B 40.4 . . ? N5 C13A N6A 110(3) . . ? N5 C13A N6 100(3) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.872 _refine_diff_density_min -1.266 _refine_diff_density_rms 0.190 _database_code_depnum_ccdc_archive 'CCDC 921021'