# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_1 #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H11 Cu I N3 O' _chemical_formula_sum 'C12 H11 Cu I N3 O' _chemical_formula_weight 403.68 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9666(16) _cell_length_b 9.4084(19) _cell_length_c 9.6154(19) _cell_angle_alpha 89.66(3) _cell_angle_beta 71.19(3) _cell_angle_gamma 69.77(3) _cell_volume 635.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3530 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 27.45 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.109 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 4.137 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5070 _exptl_absorpt_correction_T_max 0.5758 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6314 _diffrn_reflns_av_R_equivalents 0.0700 _diffrn_reflns_av_sigmaI/netI 0.0924 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2900 _reflns_number_gt 1872 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0474P)^2^+3.8647P] 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 2900 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0945 _refine_ls_R_factor_gt 0.0607 _refine_ls_wR_factor_ref 0.1664 _refine_ls_wR_factor_gt 0.1218 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.43222(19) -0.04300(12) 0.40112(13) 0.0485(4) Uani 1 1 d . . . I1 I 0.79917(10) -0.14939(7) 0.35485(7) 0.0475(2) Uani 1 1 d . . . O1 O 0.7412(13) 0.2965(10) 0.0021(9) 0.077(2) Uani 1 1 d . . . N1 N 0.3563(11) 0.0680(8) 0.2309(8) 0.0411(18) Uani 1 1 d . . . N2 N 0.5333(12) 0.3827(8) 0.2184(9) 0.0440(19) Uani 1 1 d . . . N3 N 0.3556(12) 0.7655(8) 0.4184(8) 0.0414(18) Uani 1 1 d . . . C1 C 0.2425(15) 0.0261(12) 0.1776(11) 0.051(2) Uani 1 1 d . . . H1 H 0.2221 -0.0632 0.2049 0.061 Uiso 1 1 calc R . . C2 C 0.1537(17) 0.1065(13) 0.0851(12) 0.059(3) Uani 1 1 d . . . H2 H 0.0751 0.0731 0.0513 0.071 Uiso 1 1 calc R . . C3 C 0.1851(16) 0.2376(13) 0.0443(11) 0.055(3) Uani 1 1 d . . . H3 H 0.1270 0.2951 -0.0179 0.066 Uiso 1 1 calc R . . C4 C 0.3012(17) 0.2834(12) 0.0951(11) 0.055(3) Uani 1 1 d . . . H4 H 0.3218 0.3728 0.0689 0.067 Uiso 1 1 calc R . . C5 C 0.3889(14) 0.1957(10) 0.1862(9) 0.039(2) Uani 1 1 d . . . C6 C 0.5269(16) 0.2311(10) 0.2431(11) 0.048(2) Uani 1 1 d . . . H6A H 0.4919 0.2228 0.3484 0.058 Uiso 1 1 calc R . . H6B H 0.6531 0.1555 0.1949 0.058 Uiso 1 1 calc R . . C7 C 0.4193(14) 0.5097(10) 0.3268(10) 0.041(2) Uani 1 1 d . . . C8 C 0.2649(15) 0.5056(11) 0.4435(11) 0.048(2) Uani 1 1 d . . . H8 H 0.2341 0.4185 0.4523 0.058 Uiso 1 1 calc R . . C9 C 0.1583(16) 0.6316(11) 0.5458(12) 0.054(3) Uani 1 1 d . . . H9 H 0.0550 0.6308 0.6258 0.065 Uiso 1 1 calc R . . C10 C 0.2064(15) 0.7601(11) 0.5283(11) 0.050(2) Uani 1 1 d . . . H10 H 0.1310 0.8464 0.5965 0.060 Uiso 1 1 calc R . . C11 C 0.4598(16) 0.6426(10) 0.3196(11) 0.048(2) Uani 1 1 d . . . H11 H 0.5644 0.6457 0.2423 0.057 Uiso 1 1 calc R . . C12 C 0.6472(15) 0.4069(10) 0.0946(10) 0.043(2) Uani 1 1 d . . . H12A H 0.6551 0.5024 0.0790 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0650(9) 0.0360(6) 0.0496(7) 0.0057(5) -0.0200(6) -0.0240(6) I1 0.0569(4) 0.0393(4) 0.0449(4) 0.0007(3) -0.0153(3) -0.0178(3) O1 0.086(6) 0.074(5) 0.063(5) -0.006(4) -0.005(5) -0.039(5) N1 0.051(5) 0.035(4) 0.040(4) 0.006(3) -0.015(4) -0.019(3) N2 0.058(5) 0.033(4) 0.052(5) 0.005(3) -0.025(4) -0.025(4) N3 0.052(5) 0.038(4) 0.039(4) 0.004(3) -0.013(4) -0.023(4) C1 0.057(7) 0.050(5) 0.055(6) 0.003(5) -0.021(5) -0.028(5) C2 0.063(7) 0.074(7) 0.059(7) -0.004(6) -0.031(6) -0.038(6) C3 0.056(7) 0.071(7) 0.049(6) 0.007(5) -0.026(5) -0.028(6) C4 0.078(8) 0.052(6) 0.047(6) 0.012(5) -0.029(6) -0.029(6) C5 0.053(6) 0.035(4) 0.037(5) 0.007(4) -0.018(4) -0.022(4) C6 0.067(7) 0.029(4) 0.057(6) 0.006(4) -0.026(5) -0.023(4) C7 0.057(6) 0.037(5) 0.040(5) 0.009(4) -0.022(5) -0.024(4) C8 0.060(7) 0.044(5) 0.048(6) 0.010(4) -0.018(5) -0.030(5) C9 0.060(7) 0.051(6) 0.050(6) 0.002(5) -0.007(5) -0.028(5) C10 0.054(6) 0.041(5) 0.051(6) 0.000(5) -0.013(5) -0.017(5) C11 0.070(7) 0.037(5) 0.043(5) 0.004(4) -0.017(5) -0.028(5) C12 0.064(6) 0.029(4) 0.039(5) 0.003(4) -0.010(5) -0.026(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 N1 2.078(7) . ? Cu1 N3 2.083(7) 1_545 ? Cu1 I1 2.6246(17) . ? Cu1 I1 2.6711(19) 2_656 ? Cu1 Cu1 2.717(3) 2_656 ? I1 Cu1 2.6711(19) 2_656 ? O1 C12 1.213(11) . ? N1 C1 1.338(12) . ? N1 C5 1.354(11) . ? N2 C12 1.318(12) . ? N2 C7 1.411(12) . ? N2 C6 1.460(11) . ? N3 C10 1.328(12) . ? N3 C11 1.330(12) . ? N3 Cu1 2.083(7) 1_565 ? C1 C2 1.375(14) . ? C1 H1 0.9300 . ? C2 C3 1.372(15) . ? C2 H2 0.9300 . ? C3 C4 1.360(14) . ? C3 H3 0.9300 . ? C4 C5 1.387(12) . ? C4 H4 0.9300 . ? C5 C6 1.504(13) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.383(14) . ? C7 C11 1.392(12) . ? C8 C9 1.368(14) . ? C8 H8 0.9300 . ? C9 C10 1.383(14) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 N3 107.8(3) . 1_545 ? N1 Cu1 I1 114.6(2) . . ? N3 Cu1 I1 105.0(2) 1_545 . ? N1 Cu1 I1 104.3(2) . 2_656 ? N3 Cu1 I1 106.3(2) 1_545 2_656 ? I1 Cu1 I1 118.26(6) . 2_656 ? N1 Cu1 Cu1 130.1(2) . 2_656 ? N3 Cu1 Cu1 121.8(2) 1_545 2_656 ? I1 Cu1 Cu1 59.97(6) . 2_656 ? I1 Cu1 Cu1 58.29(5) 2_656 2_656 ? Cu1 I1 Cu1 61.74(6) . 2_656 ? C1 N1 C5 117.0(8) . . ? C1 N1 Cu1 118.1(6) . . ? C5 N1 Cu1 124.1(6) . . ? C12 N2 C7 117.0(7) . . ? C12 N2 C6 121.5(8) . . ? C7 N2 C6 121.5(8) . . ? C10 N3 C11 118.1(8) . . ? C10 N3 Cu1 121.9(6) . 1_565 ? C11 N3 Cu1 120.0(7) . 1_565 ? N1 C1 C2 124.2(9) . . ? N1 C1 H1 117.9 . . ? C2 C1 H1 117.9 . . ? C3 C2 C1 117.8(10) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? C4 C3 C2 119.8(9) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 119.6(10) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 121.6(9) . . ? N1 C5 C6 114.2(7) . . ? C4 C5 C6 124.2(8) . . ? N2 C6 C5 113.6(7) . . ? N2 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? N2 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C11 118.0(9) . . ? C8 C7 N2 121.2(8) . . ? C11 C7 N2 120.8(9) . . ? C9 C8 C7 119.1(9) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 119.0(10) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? N3 C10 C9 122.8(10) . . ? N3 C10 H10 118.6 . . ? C9 C10 H10 118.6 . . ? N3 C11 C7 122.9(10) . . ? N3 C11 H11 118.5 . . ? C7 C11 H11 118.5 . . ? O1 C12 N2 115.7(8) . . ? O1 C12 H12A 122.2 . . ? N2 C12 H12A 122.2 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 I1 Cu1 123.6(2) . . . 2_656 ? N3 Cu1 I1 Cu1 -118.4(2) 1_545 . . 2_656 ? I1 Cu1 I1 Cu1 0.0 2_656 . . 2_656 ? N3 Cu1 N1 C1 12.5(8) 1_545 . . . ? I1 Cu1 N1 C1 129.0(7) . . . . ? I1 Cu1 N1 C1 -100.2(7) 2_656 . . . ? Cu1 Cu1 N1 C1 -160.5(6) 2_656 . . . ? N3 Cu1 N1 C5 -178.5(7) 1_545 . . . ? I1 Cu1 N1 C5 -62.0(8) . . . . ? I1 Cu1 N1 C5 68.8(8) 2_656 . . . ? Cu1 Cu1 N1 C5 8.5(9) 2_656 . . . ? C5 N1 C1 C2 -2.0(15) . . . . ? Cu1 N1 C1 C2 167.8(9) . . . . ? N1 C1 C2 C3 0.4(17) . . . . ? C1 C2 C3 C4 0.2(17) . . . . ? C2 C3 C4 C5 0.8(17) . . . . ? C1 N1 C5 C4 3.0(14) . . . . ? Cu1 N1 C5 C4 -166.1(8) . . . . ? C1 N1 C5 C6 -176.6(9) . . . . ? Cu1 N1 C5 C6 14.3(11) . . . . ? C3 C4 C5 N1 -2.5(16) . . . . ? C3 C4 C5 C6 177.0(10) . . . . ? C12 N2 C6 C5 -87.6(11) . . . . ? C7 N2 C6 C5 93.1(10) . . . . ? N1 C5 C6 N2 -168.9(8) . . . . ? C4 C5 C6 N2 11.5(14) . . . . ? C12 N2 C7 C8 164.4(9) . . . . ? C6 N2 C7 C8 -16.2(13) . . . . ? C12 N2 C7 C11 -15.9(13) . . . . ? C6 N2 C7 C11 163.4(9) . . . . ? C11 C7 C8 C9 0.5(15) . . . . ? N2 C7 C8 C9 -179.9(9) . . . . ? C7 C8 C9 C10 0.9(16) . . . . ? C11 N3 C10 C9 1.5(15) . . . . ? Cu1 N3 C10 C9 -176.9(8) 1_565 . . . ? C8 C9 C10 N3 -2.0(16) . . . . ? C10 N3 C11 C7 0.0(14) . . . . ? Cu1 N3 C11 C7 178.4(7) 1_565 . . . ? C8 C7 C11 N3 -0.9(15) . . . . ? N2 C7 C11 N3 179.4(8) . . . . ? C7 N2 C12 O1 -178.7(9) . . . . ? C6 N2 C12 O1 2.0(15) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.959 _refine_diff_density_min -1.990 _refine_diff_density_rms 0.229 #===END # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.033 0.033 0.274 7 0 ' ' 2 0.467 0.033 0.774 7 1 ' ' 3 0.065 0.125 0.202 8 1 ' ' 4 0.750 0.250 0.331 110 19 ' ' 5 0.435 0.125 0.702 8 1 ' ' 6 0.750 0.250 0.831 110 19 ' ' 7 0.437 0.383 0.208 9 1 ' ' 8 0.062 0.383 0.708 9 1 ' ' 9 0.471 0.475 0.281 6 0 ' ' 10 0.029 0.475 0.781 6 0 ' ' 11 0.967 0.533 0.226 7 0 ' ' 12 0.533 0.533 0.726 7 0 ' ' 13 0.250 0.750 0.169 110 19 ' ' 14 0.935 0.625 0.298 8 1 ' ' 15 0.250 0.750 0.669 110 19 ' ' 16 0.565 0.625 0.798 9 1 ' ' 17 0.562 0.883 0.292 10 1 ' ' 18 0.937 0.883 0.792 9 1 ' ' 19 0.529 0.975 0.219 6 0 ' ' 20 0.971 0.975 0.719 6 0 ' ' _platon_squeeze_details ; Four acetonitrile molecules added to total atom count. ; _database_code_depnum_ccdc_archive 'CCDC 934839' ####################################################################### # # 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_2 #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'Cu3 I2 (C4 H6 N3) (C18 H15 P)2, C2 H3 N' _chemical_formula_sum 'C42 H39 Cu3 I2 N4 P2' _chemical_formula_weight 1106.13 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' P P 0.1023 0.0942 '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 'P ccn' _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 23.0737(14) _cell_length_b 11.5118(7) _cell_length_c 16.6416(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4420.3(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 18478 _cell_measurement_theta_min 3.02 _cell_measurement_theta_max 27.42 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.662 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 2.932 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5481 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 40867 _diffrn_reflns_av_R_equivalents 0.0797 _diffrn_reflns_av_sigmaI/netI 0.0501 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5038 _reflns_number_gt 3002 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXL-97 _computing_publication_material SHELXL-97 _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^)+(0.0710P)^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 5038 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0966 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1531 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _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 I1 I 0.698243(19) 0.90553(3) 0.20636(2) 0.06636(19) Uani 1 1 d . . . Cu1 Cu 0.69470(4) 0.67658(7) 0.14223(4) 0.0718(3) Uani 1 1 d . . . Cu2 Cu 0.7500 0.7500 0.29044(5) 0.0660(3) Uani 1 2 d S . . P1 P 0.62159(7) 0.57420(13) 0.18785(9) 0.0600(4) Uani 1 1 d . . . N1 N 0.7500 0.7500 0.4077(3) 0.0563(16) Uani 1 2 d S . . N2 N 0.7249(2) 0.7833(4) 0.5359(2) 0.0628(12) Uani 1 1 d . . . C1 C 0.55303(19) 0.6246(4) 0.1461(3) 0.0742(17) Uani 1 1 d G . . C2 C 0.5098(3) 0.5489(4) 0.1207(4) 0.163(5) Uani 1 1 d G . . H2 H 0.5156 0.4691 0.1237 0.210 Uiso 1 1 calc R . . C3 C 0.4580(2) 0.5925(7) 0.0908(5) 0.164(5) Uani 1 1 d G . . H3 H 0.4291 0.5418 0.0738 0.287 Uiso 1 1 calc R . . C4 C 0.4493(2) 0.7118(7) 0.0862(4) 0.160(5) Uani 1 1 d G . . H4 H 0.4146 0.7409 0.0662 0.193 Uiso 1 1 calc R . . C5 C 0.4925(3) 0.7875(5) 0.1116(3) 0.117(3) Uani 1 1 d G . . H5 H 0.4867 0.8673 0.1086 0.140 Uiso 1 1 calc R . . C6 C 0.5444(2) 0.7439(4) 0.1415(3) 0.100(2) Uani 1 1 d G . . H6 H 0.5733 0.7946 0.1585 0.120 Uiso 1 1 calc R . . C7 C 0.6253(2) 0.4208(3) 0.1627(2) 0.0711(17) Uani 1 1 d G . . C8 C 0.5942(2) 0.3366(4) 0.2044(3) 0.101(3) Uani 1 1 d G . . H8 H 0.5710 0.3578 0.2476 0.122 Uiso 1 1 calc R . . C9 C 0.5979(3) 0.2208(4) 0.1814(4) 0.117(3) Uani 1 1 d G . . H9 H 0.5771 0.1645 0.2092 0.140 Uiso 1 1 calc R . . C10 C 0.6327(3) 0.1891(3) 0.1168(4) 0.112(3) Uani 1 1 d G . . H10 H 0.6351 0.1116 0.1014 0.134 Uiso 1 1 calc R . . C11 C 0.6638(2) 0.2732(5) 0.0752(3) 0.103(3) Uani 1 1 d G . . H11 H 0.6870 0.2520 0.0320 0.124 Uiso 1 1 calc R . . C12 C 0.66007(19) 0.3891(4) 0.0982(2) 0.0767(18) Uani 1 1 d G . . H12 H 0.6809 0.4454 0.0703 0.092 Uiso 1 1 calc R . . C13 C 0.61036(19) 0.5739(4) 0.29757(17) 0.0661(16) Uani 1 1 d G . . C14 C 0.56003(17) 0.6166(4) 0.3327(3) 0.091(2) Uani 1 1 d G . . H14 H 0.5304 0.6458 0.3006 0.109 Uiso 1 1 calc R . . C15 C 0.5540(2) 0.6157(5) 0.4158(3) 0.115(3) Uani 1 1 d G . . H15 H 0.5203 0.6443 0.4393 0.138 Uiso 1 1 calc R . . C16 C 0.5983(3) 0.5722(5) 0.46377(17) 0.106(3) Uani 1 1 d G . . H16 H 0.5942 0.5716 0.5194 0.128 Uiso 1 1 calc R . . C17 C 0.6486(2) 0.5295(4) 0.4286(2) 0.093(2) Uani 1 1 d G . . H17 H 0.6782 0.5003 0.4607 0.112 Uiso 1 1 calc R . . C18 C 0.65464(16) 0.5304(4) 0.3455(2) 0.0782(18) Uani 1 1 d G . . H18 H 0.6883 0.5018 0.3220 0.094 Uiso 1 1 calc R . . C19 C 0.7111(3) 0.8002(5) 0.4588(3) 0.0584(14) Uani 1 1 d . . . C20 C 0.6604(3) 0.8686(6) 0.4332(3) 0.0771(19) Uani 1 1 d . . . H20A H 0.6330 0.8730 0.4765 0.116 Uiso 1 1 calc R . . H20B H 0.6425 0.8318 0.3877 0.116 Uiso 1 1 calc R . . H20C H 0.6725 0.9455 0.4186 0.116 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0843(3) 0.0595(3) 0.0553(3) 0.00207(16) -0.00674(18) 0.01294(19) Cu1 0.0833(6) 0.0839(6) 0.0480(4) 0.0064(4) 0.0078(4) -0.0173(4) Cu2 0.0878(8) 0.0689(7) 0.0413(5) 0.000 0.000 0.0143(6) P1 0.0669(10) 0.0634(9) 0.0498(8) 0.0002(7) 0.0069(7) -0.0017(7) N1 0.072(4) 0.063(4) 0.033(3) 0.000 0.000 0.020(3) N2 0.075(3) 0.070(3) 0.044(2) -0.003(2) 0.000(2) 0.019(2) C1 0.068(4) 0.091(5) 0.064(4) -0.021(3) 0.005(3) 0.002(4) C2 0.133(10) 0.226(14) 0.134(8) -0.054(9) -0.052(7) 0.057(9) C3 0.136(10) 0.225(14) 0.131(8) -0.052(9) -0.052(7) 0.059(9) C4 0.131(10) 0.221(14) 0.129(8) -0.056(9) -0.057(7) 0.054(9) C5 0.108(7) 0.150(8) 0.092(6) 0.039(6) 0.024(5) 0.048(6) C6 0.085(6) 0.101(6) 0.114(6) 0.032(5) 0.010(4) 0.013(5) C7 0.077(4) 0.071(4) 0.065(4) -0.005(3) 0.010(3) -0.001(3) C8 0.108(6) 0.081(5) 0.115(6) -0.004(4) 0.035(5) -0.024(5) C9 0.132(8) 0.069(5) 0.149(8) -0.002(5) -0.004(6) -0.023(5) C10 0.156(9) 0.072(5) 0.107(6) -0.015(5) -0.049(6) 0.013(5) C11 0.147(8) 0.095(6) 0.067(4) -0.013(4) -0.019(5) 0.044(6) C12 0.098(5) 0.078(4) 0.054(3) -0.002(3) 0.003(3) 0.016(4) C13 0.081(4) 0.063(4) 0.055(3) 0.001(3) 0.014(3) -0.005(3) C14 0.101(6) 0.099(5) 0.073(4) 0.009(4) 0.028(4) 0.014(4) C15 0.141(8) 0.139(7) 0.065(4) 0.000(4) 0.036(5) 0.026(6) C16 0.151(8) 0.113(6) 0.056(4) 0.004(4) 0.022(5) 0.015(6) C17 0.113(6) 0.102(5) 0.065(4) 0.021(4) -0.009(4) -0.004(5) C18 0.084(5) 0.094(5) 0.056(3) 0.010(3) 0.002(3) 0.002(4) C19 0.072(4) 0.059(3) 0.044(3) 0.003(2) -0.001(3) 0.010(3) C20 0.093(5) 0.088(4) 0.050(3) 0.001(3) -0.003(3) 0.033(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Cu2 2.5671(6) . ? I1 Cu1 2.8447(9) . ? I1 Cu1 2.8520(6) 2_665 ? Cu1 N2 1.958(4) 7_575 ? Cu1 P1 2.1934(5) . ? Cu1 I1 2.8520(6) 2_665 ? Cu1 Cu2 2.9027(6) . ? Cu2 N1 1.952(5) . ? Cu2 I1 2.5671(6) 2_665 ? Cu2 Cu1 2.9027(6) 2_665 ? P1 C7 1.817(4) . ? P1 C1 1.823(4) . ? P1 C13 1.844(3) . ? N1 C19 1.364(6) 2_665 ? N1 C19 1.364(6) . ? N2 C19 1.336(6) . ? N2 N2 1.387(9) 2_665 ? N2 Cu1 1.958(4) 7_576 ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 H2 0.9300 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 H4 0.9300 . ? C5 C6 1.3900 . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.3900 . ? C7 C12 1.3900 . ? C8 C9 1.3900 . ? C8 H8 0.9300 . ? C9 C10 1.3900 . ? C9 H9 0.9300 . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 C12 1.3900 . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? C13 C14 1.3900 . ? C13 C18 1.3900 . ? C14 C15 1.3900 . ? C14 H14 0.9300 . ? C15 C16 1.3900 . ? C15 H15 0.9300 . ? C16 C17 1.3900 . ? C16 H16 0.9300 . ? C17 C18 1.3900 . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C20 1.474(8) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cu2 I1 Cu1 64.64(2) . . ? Cu2 I1 Cu1 64.52(2) . 2_665 ? Cu1 I1 Cu1 65.00(3) . 2_665 ? N2 Cu1 P1 135.54(1) 7_575 . ? N2 Cu1 I1 96.33(14) 7_575 . ? P1 Cu1 I1 112.96(5) . . ? N2 Cu1 I1 96.20(2) 7_575 2_665 ? P1 Cu1 I1 111.01(5) . 2_665 ? I1 Cu1 I1 98.15(3) . 2_665 ? N2 Cu1 Cu2 122.88(14) 7_575 . ? P1 Cu1 Cu2 101.56(5) . . ? I1 Cu1 Cu2 53.046(16) . . ? I1 Cu1 Cu2 52.976(16) 2_665 . ? N1 Cu2 I1 123.029(18) . . ? N1 Cu2 I1 123.029(18) . 2_665 ? I1 Cu2 I1 113.94(4) . 2_665 ? N1 Cu2 Cu1 148.181(16) . . ? I1 Cu2 Cu1 62.32(2) . . ? I1 Cu2 Cu1 62.50(3) 2_665 . ? N1 Cu2 Cu1 148.181(16) . 2_665 ? I1 Cu2 Cu1 62.50(3) . 2_665 ? I1 Cu2 Cu1 62.32(2) 2_665 2_665 ? Cu1 Cu2 Cu1 63.64(3) . 2_665 ? C7 P1 C1 105.2(2) . . ? C7 P1 C13 103.5(2) . . ? C1 P1 C13 104.9(2) . . ? C7 P1 Cu1 113.98(16) . . ? C1 P1 Cu1 111.36(19) . . ? C13 P1 Cu1 116.85(16) . . ? C19 N1 C19 102.9(6) 2_665 . ? C19 N1 Cu2 128.5(3) 2_665 . ? C19 N1 Cu2 128.5(3) . . ? C19 N2 N2 106.2(3) . 2_665 ? C19 N2 Cu1 138.5(4) . 7_576 ? N2 N2 Cu1 115.30(13) 2_665 7_576 ? C2 C1 C6 120.0 . . ? C2 C1 P1 122.6(3) . . ? C6 C1 P1 117.4(3) . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? C8 C7 C12 120.0 . . ? C8 C7 P1 122.6(3) . . ? C12 C7 P1 117.4(3) . . ? C7 C8 C9 120.0 . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C10 C9 C8 120.0 . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.0 . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C11 C12 C7 120.0 . . ? C11 C12 H12 120.0 . . ? C7 C12 H12 120.0 . . ? C14 C13 C18 120.0 . . ? C14 C13 P1 122.2(2) . . ? C18 C13 P1 117.8(2) . . ? C15 C14 C13 120.0 . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.0 . . ? C14 C15 H15 120.0 . . ? C16 C15 H15 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 120.0 . . ? C16 C17 H17 120.0 . . ? C18 C17 H17 120.0 . . ? C17 C18 C13 120.0 . . ? C17 C18 H18 120.0 . . ? C13 C18 H18 120.0 . . ? N2 C19 N1 112.3(5) . . ? N2 C19 C20 123.0(5) . . ? N1 C19 C20 124.6(4) . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cu2 I1 Cu1 N2 -126.87(16) . . . 7_575 ? Cu1 I1 Cu1 N2 -54.58(15) 2_665 . . 7_575 ? Cu2 I1 Cu1 P1 87.34(5) . . . . ? Cu1 I1 Cu1 P1 159.64(6) 2_665 . . . ? Cu2 I1 Cu1 I1 -29.656(19) . . . 2_665 ? Cu1 I1 Cu1 I1 42.64(3) 2_665 . . 2_665 ? Cu1 I1 Cu1 Cu2 72.29(2) 2_665 . . . ? Cu1 I1 Cu2 N1 -143.460(18) . . . . ? Cu1 I1 Cu2 N1 143.530(17) 2_665 . . . ? Cu1 I1 Cu2 I1 36.540(17) . . . 2_665 ? Cu1 I1 Cu2 I1 -36.470(17) 2_665 . . 2_665 ? Cu1 I1 Cu2 Cu1 -73.01(3) 2_665 . . . ? Cu1 I1 Cu2 Cu1 73.01(3) . . . 2_665 ? N2 Cu1 Cu2 N1 180.00(19) 7_575 . . . ? P1 Cu1 Cu2 N1 -1.36(7) . . . . ? I1 Cu1 Cu2 N1 108.78(3) . . . . ? I1 Cu1 Cu2 N1 -109.06(3) 2_665 . . . ? N2 Cu1 Cu2 I1 71.22(19) 7_575 . . . ? P1 Cu1 Cu2 I1 -110.14(5) . . . . ? I1 Cu1 Cu2 I1 142.16(2) 2_665 . . . ? N2 Cu1 Cu2 I1 -70.94(19) 7_575 . . 2_665 ? P1 Cu1 Cu2 I1 107.70(5) . . . 2_665 ? I1 Cu1 Cu2 I1 -142.16(2) . . . 2_665 ? N2 Cu1 Cu2 Cu1 0.00(19) 7_575 . . 2_665 ? P1 Cu1 Cu2 Cu1 178.64(7) . . . 2_665 ? I1 Cu1 Cu2 Cu1 -71.22(3) . . . 2_665 ? I1 Cu1 Cu2 Cu1 70.94(3) 2_665 . . 2_665 ? N2 Cu1 P1 C7 63.5(3) 7_575 . . . ? I1 Cu1 P1 C7 -169.42(17) . . . . ? I1 Cu1 P1 C7 -60.29(18) 2_665 . . . ? Cu2 Cu1 P1 C7 -114.85(18) . . . . ? N2 Cu1 P1 C1 -55.4(3) 7_575 . . . ? I1 Cu1 P1 C1 71.71(18) . . . . ? I1 Cu1 P1 C1 -179.16(17) 2_665 . . . ? Cu2 Cu1 P1 C1 126.28(17) . . . . ? N2 Cu1 P1 C13 -175.8(3) 7_575 . . . ? I1 Cu1 P1 C13 -48.72(18) . . . . ? I1 Cu1 P1 C13 60.41(17) 2_665 . . . ? Cu2 Cu1 P1 C13 5.85(17) . . . . ? I1 Cu2 N1 C19 -156.5(3) . . . 2_665 ? I1 Cu2 N1 C19 23.5(3) 2_665 . . 2_665 ? Cu1 Cu2 N1 C19 113.7(3) . . . 2_665 ? Cu1 Cu2 N1 C19 -66.3(3) 2_665 . . 2_665 ? I1 Cu2 N1 C19 23.5(3) . . . . ? I1 Cu2 N1 C19 -156.5(3) 2_665 . . . ? Cu1 Cu2 N1 C19 -66.3(3) . . . . ? Cu1 Cu2 N1 C19 113.7(3) 2_665 . . . ? C7 P1 C1 C2 14.5(4) . . . . ? C13 P1 C1 C2 -94.3(4) . . . . ? Cu1 P1 C1 C2 138.4(3) . . . . ? C7 P1 C1 C6 -166.8(3) . . . . ? C13 P1 C1 C6 84.4(3) . . . . ? Cu1 P1 C1 C6 -42.8(3) . . . . ? C6 C1 C2 C3 0.0 . . . . ? P1 C1 C2 C3 178.7(4) . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C3 C4 C5 C6 0.0 . . . . ? C4 C5 C6 C1 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? P1 C1 C6 C5 -178.8(4) . . . . ? C1 P1 C7 C8 -77.4(3) . . . . ? C13 P1 C7 C8 32.4(3) . . . . ? Cu1 P1 C7 C8 160.3(2) . . . . ? C1 P1 C7 C12 101.3(3) . . . . ? C13 P1 C7 C12 -148.9(3) . . . . ? Cu1 P1 C7 C12 -21.0(3) . . . . ? C12 C7 C8 C9 0.0 . . . . ? P1 C7 C8 C9 178.7(4) . . . . ? C7 C8 C9 C10 0.0 . . . . ? C8 C9 C10 C11 0.0 . . . . ? C9 C10 C11 C12 0.0 . . . . ? C10 C11 C12 C7 0.0 . . . . ? C8 C7 C12 C11 0.0 . . . . ? P1 C7 C12 C11 -178.8(3) . . . . ? C7 P1 C13 C14 -115.6(3) . . . . ? C1 P1 C13 C14 -5.6(3) . . . . ? Cu1 P1 C13 C14 118.3(2) . . . . ? C7 P1 C13 C18 65.1(3) . . . . ? C1 P1 C13 C18 175.2(3) . . . . ? Cu1 P1 C13 C18 -61.0(3) . . . . ? C18 C13 C14 C15 0.0 . . . . ? P1 C13 C14 C15 -179.2(3) . . . . ? C13 C14 C15 C16 0.0 . . . . ? C14 C15 C16 C17 0.0 . . . . ? C15 C16 C17 C18 0.0 . . . . ? C16 C17 C18 C13 0.0 . . . . ? C14 C13 C18 C17 0.0 . . . . ? P1 C13 C18 C17 179.3(3) . . . . ? N2 N2 C19 N1 -1.0(8) 2_665 . . . ? Cu1 N2 C19 N1 179.8(4) 7_576 . . . ? N2 N2 C19 C20 -179.4(7) 2_665 . . . ? Cu1 N2 C19 C20 1.4(11) 7_576 . . . ? C19 N1 C19 N2 0.4(3) 2_665 . . . ? Cu2 N1 C19 N2 -179.6(3) . . . . ? C19 N1 C19 C20 178.7(8) 2_665 . . . ? Cu2 N1 C19 C20 -1.3(8) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.789 _refine_diff_density_min -0.832 _refine_diff_density_rms 0.108 _database_code_depnum_ccdc_archive 'CCDC 934840' ####################################################################### # # 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_3 #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H9 Cu2 I2 N3' _chemical_formula_sum 'C11 H9 Cu2 I2 N3' _chemical_formula_weight 564.09 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.825(2) _cell_length_b 12.261(3) _cell_length_c 11.798(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.34(3) _cell_angle_gamma 90.00 _cell_volume 1418.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 6566 _cell_measurement_theta_min 3.16 _cell_measurement_theta_max 27.46 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.641 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 7.333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2615 _exptl_absorpt_correction_T_max 0.4059 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13616 _diffrn_reflns_av_R_equivalents 0.0989 _diffrn_reflns_av_sigmaI/netI 0.0829 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.11 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3236 _reflns_number_gt 2123 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0519P)^2^+1.9576P] 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 3236 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0491 _refine_ls_wR_factor_ref 0.1369 _refine_ls_wR_factor_gt 0.1025 _refine_ls_goodness_of_fit_ref 1.055 _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 I1 I 0.22471(6) 0.48981(4) 0.49715(5) 0.0422(2) Uani 1 1 d . . . I2 I -0.01255(6) 0.29090(5) 0.24835(5) 0.0467(2) Uani 1 1 d . . . Cu1 Cu 0.12110(12) 0.30017(9) 0.44232(9) 0.0472(3) Uani 1 1 d . . . Cu2 Cu 0.02259(14) 0.52599(10) 0.62875(11) 0.0579(4) Uani 1 1 d . . . N1 N 0.0381(7) 0.1919(5) 0.5548(6) 0.0350(15) Uani 1 1 d . . . N2 N 0.2769(7) 0.1809(6) 0.4601(6) 0.0410(17) Uani 1 1 d . . . N3 N 0.5216(7) 0.0910(6) 0.2527(6) 0.0404(17) Uani 1 1 d . . . C1 C -0.0836(9) 0.1967(7) 0.6005(8) 0.044(2) Uani 1 1 d . . . H1 H -0.1418 0.2543 0.5808 0.053 Uiso 1 1 calc R . . C2 C -0.1253(10) 0.1199(8) 0.6750(8) 0.052(2) Uani 1 1 d . . . H2 H -0.2085 0.1277 0.7078 0.062 Uiso 1 1 calc R . . C3 C -0.0455(11) 0.0324(8) 0.7009(9) 0.056(3) Uani 1 1 d . . . H3 H -0.0736 -0.0207 0.7507 0.068 Uiso 1 1 calc R . . C4 C 0.0777(10) 0.0233(8) 0.6524(8) 0.053(2) Uani 1 1 d . . . H4 H 0.1337 -0.0365 0.6686 0.063 Uiso 1 1 calc R . . C5 C 0.1180(9) 0.1040(7) 0.5791(7) 0.039(2) Uani 1 1 d . . . C6 C 0.2454(9) 0.1002(7) 0.5226(7) 0.040(2) Uani 1 1 d . . . H6 H 0.3031 0.0403 0.5316 0.048 Uiso 1 1 calc R . . C7 C 0.4004(9) 0.1741(7) 0.4011(7) 0.0371(19) Uani 1 1 d . . . C8 C 0.4128(9) 0.0984(7) 0.3158(8) 0.046(2) Uani 1 1 d . . . H8 H 0.3415 0.0496 0.3013 0.055 Uiso 1 1 calc R . . C9 C 0.6214(9) 0.1621(7) 0.2746(6) 0.0382(19) Uani 1 1 d . . . H9 H 0.6972 0.1595 0.2310 0.046 Uiso 1 1 calc R . . C10 C 0.6179(10) 0.2402(8) 0.3595(7) 0.046(2) Uani 1 1 d . . . H10 H 0.6913 0.2870 0.3741 0.055 Uiso 1 1 calc R . . C11 C 0.5043(9) 0.2470(8) 0.4217(7) 0.046(2) Uani 1 1 d . . . H11 H 0.4980 0.3006 0.4769 0.056 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0385(4) 0.0403(3) 0.0483(4) -0.0038(3) 0.0077(3) -0.0030(2) I2 0.0471(4) 0.0487(4) 0.0439(4) -0.0015(3) -0.0011(3) -0.0041(3) Cu1 0.0522(8) 0.0408(6) 0.0489(6) 0.0066(5) 0.0050(5) 0.0018(5) Cu2 0.0584(9) 0.0518(7) 0.0652(8) 0.0183(6) 0.0182(7) 0.0087(6) N1 0.030(4) 0.032(3) 0.042(4) 0.000(3) 0.001(3) 0.000(3) N2 0.039(5) 0.038(4) 0.047(4) -0.007(3) 0.014(3) -0.004(3) N3 0.041(5) 0.033(4) 0.048(4) -0.001(3) 0.008(3) -0.005(3) C1 0.035(5) 0.036(5) 0.060(6) 0.005(4) 0.001(4) 0.003(4) C2 0.041(6) 0.049(6) 0.067(6) -0.006(5) 0.018(5) -0.010(4) C3 0.063(7) 0.040(5) 0.069(6) 0.013(5) 0.032(6) -0.006(5) C4 0.049(7) 0.047(5) 0.064(6) 0.005(5) 0.008(5) 0.005(4) C5 0.038(6) 0.036(5) 0.044(5) -0.005(4) 0.002(4) 0.003(4) C6 0.038(5) 0.036(5) 0.047(5) 0.003(4) 0.013(4) 0.002(4) C7 0.038(5) 0.038(4) 0.036(4) -0.007(4) 0.005(4) 0.003(4) C8 0.034(5) 0.044(5) 0.062(6) -0.006(5) 0.015(4) -0.004(4) C9 0.034(5) 0.048(5) 0.033(4) 0.000(4) 0.000(3) -0.006(4) C10 0.039(6) 0.052(5) 0.047(5) 0.000(5) -0.001(4) -0.010(4) C11 0.035(5) 0.057(5) 0.047(5) -0.017(5) 0.001(4) -0.012(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Cu1 2.6048(13) . ? I1 Cu2 2.6285(15) . ? I1 Cu2 2.7797(18) 3_566 ? I2 Cu1 2.5738(15) . ? I2 Cu2 2.6777(15) 3_566 ? Cu1 N1 2.077(7) . ? Cu1 N2 2.119(7) . ? Cu1 Cu2 2.665(2) 3_566 ? Cu2 N3 2.049(7) 4_566 ? Cu2 Cu1 2.665(2) 3_566 ? Cu2 I2 2.6777(15) 3_566 ? Cu2 I1 2.7797(18) 3_566 ? N1 C1 1.342(10) . ? N1 C5 1.355(10) . ? N2 C6 1.282(10) . ? N2 C7 1.436(10) . ? N3 C9 1.326(10) . ? N3 C8 1.341(10) . ? N3 Cu2 2.049(7) 4_665 ? C1 C2 1.366(12) . ? C1 H1 0.9300 . ? C2 C3 1.353(14) . ? C2 H2 0.9300 . ? C3 C4 1.373(13) . ? C3 H3 0.9300 . ? C4 C5 1.387(12) . ? C4 H4 0.9300 . ? C5 C6 1.452(11) . ? C6 H6 0.9300 . ? C7 C11 1.368(12) . ? C7 C8 1.379(11) . ? C8 H8 0.9300 . ? C9 C10 1.388(12) . ? C9 H9 0.9300 . ? C10 C11 1.374(12) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cu1 I1 Cu2 89.98(4) . . ? Cu1 I1 Cu2 59.22(4) . 3_566 ? Cu2 I1 Cu2 70.16(5) . 3_566 ? Cu1 I2 Cu2 60.95(4) . 3_566 ? N1 Cu1 N2 78.7(3) . . ? N1 Cu1 I2 109.9(2) . . ? N2 Cu1 I2 112.7(2) . . ? N1 Cu1 I1 125.0(2) . . ? N2 Cu1 I1 108.8(2) . . ? I2 Cu1 I1 115.59(4) . . ? N1 Cu1 Cu2 119.46(19) . 3_566 ? N2 Cu1 Cu2 161.77(19) . 3_566 ? I2 Cu1 Cu2 61.45(4) . 3_566 ? I1 Cu1 Cu2 63.66(5) . 3_566 ? N3 Cu2 I1 109.8(2) 4_566 . ? N3 Cu2 Cu1 139.5(2) 4_566 3_566 ? I1 Cu2 Cu1 110.7(5) . 3_566 ? N3 Cu2 I2 101.5(2) 4_566 3_566 ? I1 Cu2 I2 121.0(2) . 3_566 ? Cu1 Cu2 I2 57.60(4) 3_566 3_566 ? N3 Cu2 I1 107.0(2) 4_566 3_566 ? I1 Cu2 I1 109.8(5) . 3_566 ? Cu1 Cu2 I1 57.12(4) 3_566 3_566 ? I2 Cu2 I1 106.81(5) 3_566 3_566 ? C1 N1 C5 118.0(7) . . ? C1 N1 Cu1 128.4(5) . . ? C5 N1 Cu1 113.6(5) . . ? C6 N2 C7 118.2(7) . . ? C6 N2 Cu1 113.1(6) . . ? C7 N2 Cu1 128.2(5) . . ? C9 N3 C8 116.9(7) . . ? C9 N3 Cu2 124.4(6) . 4_665 ? C8 N3 Cu2 118.8(6) . 4_665 ? N1 C1 C2 122.4(8) . . ? N1 C1 H1 118.8 . . ? C2 C1 H1 118.8 . . ? C3 C2 C1 120.0(9) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 118.9(9) . . ? C2 C3 H3 120.5 . . ? C4 C3 H3 120.5 . . ? C3 C4 C5 119.5(9) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 121.1(8) . . ? N1 C5 C6 115.6(7) . . ? C4 C5 C6 123.3(8) . . ? N2 C6 C5 118.8(8) . . ? N2 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C11 C7 C8 118.2(8) . . ? C11 C7 N2 121.3(7) . . ? C8 C7 N2 120.4(8) . . ? N3 C8 C7 123.9(8) . . ? N3 C8 H8 118.0 . . ? C7 C8 H8 118.0 . . ? N3 C9 C10 123.0(8) . . ? N3 C9 H9 118.5 . . ? C10 C9 H9 118.5 . . ? C11 C10 C9 118.9(8) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C7 C11 C10 119.1(8) . . ? C7 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cu2 I2 Cu1 N1 113.5(2) 3_566 . . . ? Cu2 I2 Cu1 N2 -160.8(2) 3_566 . . . ? Cu2 I2 Cu1 I1 -34.84(5) 3_566 . . . ? Cu2 I1 Cu1 N1 -42.1(2) . . . . ? Cu2 I1 Cu1 N1 -108.8(2) 3_566 . . . ? Cu2 I1 Cu1 N2 -131.2(2) . . . . ? Cu2 I1 Cu1 N2 162.0(2) 3_566 . . . ? Cu2 I1 Cu1 I2 100.80(6) . . . . ? Cu2 I1 Cu1 I2 34.06(5) 3_566 . . . ? Cu2 I1 Cu1 Cu2 66.74(5) . . . 3_566 ? Cu1 I1 Cu2 N3 60.3(2) . . . 4_566 ? Cu2 I1 Cu2 N3 117.4(2) 3_566 . . 4_566 ? Cu1 I1 Cu2 Cu1 -118.33(6) . . . 3_566 ? Cu2 I1 Cu2 Cu1 -61.27(5) 3_566 . . 3_566 ? Cu1 I1 Cu2 I2 177.85(6) . . . 3_566 ? Cu2 I1 Cu2 I2 -125.09(7) 3_566 . . 3_566 ? Cu1 I1 Cu2 I1 -57.05(5) . . . 3_566 ? Cu2 I1 Cu2 I1 0.0 3_566 . . 3_566 ? N2 Cu1 N1 C1 -178.5(8) . . . . ? I2 Cu1 N1 C1 -68.3(7) . . . . ? I1 Cu1 N1 C1 76.4(8) . . . . ? Cu2 Cu1 N1 C1 -0.5(8) 3_566 . . . ? N2 Cu1 N1 C5 -1.5(6) . . . . ? I2 Cu1 N1 C5 108.7(5) . . . . ? I1 Cu1 N1 C5 -106.6(5) . . . . ? Cu2 Cu1 N1 C5 176.4(5) 3_566 . . . ? N1 Cu1 N2 C6 3.5(6) . . . . ? I2 Cu1 N2 C6 -103.5(6) . . . . ? I1 Cu1 N2 C6 126.9(6) . . . . ? Cu2 Cu1 N2 C6 -170.8(5) 3_566 . . . ? N1 Cu1 N2 C7 175.1(7) . . . . ? I2 Cu1 N2 C7 68.1(7) . . . . ? I1 Cu1 N2 C7 -61.5(7) . . . . ? Cu2 Cu1 N2 C7 0.8(12) 3_566 . . . ? C5 N1 C1 C2 3.9(13) . . . . ? Cu1 N1 C1 C2 -179.3(6) . . . . ? N1 C1 C2 C3 -3.1(15) . . . . ? C1 C2 C3 C4 0.8(16) . . . . ? C2 C3 C4 C5 0.6(16) . . . . ? C1 N1 C5 C4 -2.4(12) . . . . ? Cu1 N1 C5 C4 -179.7(7) . . . . ? C1 N1 C5 C6 176.9(7) . . . . ? Cu1 N1 C5 C6 -0.4(9) . . . . ? C3 C4 C5 N1 0.2(14) . . . . ? C3 C4 C5 C6 -179.0(9) . . . . ? C7 N2 C6 C5 -177.5(7) . . . . ? Cu1 N2 C6 C5 -5.0(10) . . . . ? N1 C5 C6 N2 3.8(12) . . . . ? C4 C5 C6 N2 -177.0(8) . . . . ? C6 N2 C7 C11 -118.5(10) . . . . ? Cu1 N2 C7 C11 70.2(11) . . . . ? C6 N2 C7 C8 66.4(11) . . . . ? Cu1 N2 C7 C8 -104.8(8) . . . . ? C9 N3 C8 C7 -0.5(13) . . . . ? Cu2 N3 C8 C7 -179.7(7) 4_665 . . . ? C11 C7 C8 N3 0.9(14) . . . . ? N2 C7 C8 N3 176.2(8) . . . . ? C8 N3 C9 C10 1.1(13) . . . . ? Cu2 N3 C9 C10 -179.7(6) 4_665 . . . ? N3 C9 C10 C11 -2.2(13) . . . . ? C8 C7 C11 C10 -2.0(14) . . . . ? N2 C7 C11 C10 -177.2(8) . . . . ? C9 C10 C11 C7 2.6(14) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.136 _refine_diff_density_min -1.422 _refine_diff_density_rms 0.238 _database_code_depnum_ccdc_archive 'CCDC 934841' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_4 #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H22 Cu4 I4 N6, H2 O' _chemical_formula_sum 'C22 H24 Cu4 I4 N6 O' _chemical_formula_weight 1150.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c' _symmetry_space_group_name_Hall '-P 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 18.782(4) _cell_length_b 9.3645(19) _cell_length_c 18.609(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.15(3) _cell_angle_gamma 90.00 _cell_volume 3247.5(11) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 18763 _cell_measurement_theta_min 3.09 _cell_measurement_theta_max 27.45 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2136 _exptl_absorpt_coefficient_mu 6.412 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3755 _exptl_absorpt_correction_T_max 0.4672 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 48566 _diffrn_reflns_av_R_equivalents 0.0875 _diffrn_reflns_av_sigmaI/netI 0.0554 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7416 _reflns_number_gt 4233 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0964P)^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 SHELXL _refine_ls_extinction_coef 0.0022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7416 _refine_ls_number_parameters 345 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0955 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1933 _refine_ls_wR_factor_gt 0.1434 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 0.20804(7) 0.16777(13) 0.42287(6) 0.0719(4) Uani 1 1 d . . . Cu2 Cu 0.30646(7) 0.34805(14) 0.38325(8) 0.0778(4) Uani 1 1 d . . . Cu3 Cu 0.18033(8) 0.32938(14) 0.30619(7) 0.0797(4) Uani 1 1 d . . . Cu4 Cu 0.27053(8) 0.08843(14) 0.30867(7) 0.0779(4) Uani 1 1 d . . . I1 I 0.19110(4) 0.44902(7) 0.44035(4) 0.0698(2) Uani 1 1 d . . . I2 I 0.12348(4) 0.06998(7) 0.29974(3) 0.0692(2) Uani 1 1 d . . . I3 I 0.34535(4) 0.08638(7) 0.43915(3) 0.0679(2) Uani 1 1 d . . . I4 I 0.29720(4) 0.32391(8) 0.23676(4) 0.0817(3) Uani 1 1 d . . . N1 N 0.1586(5) 0.0615(8) 0.4979(4) 0.067(2) Uani 1 1 d . . . N2 N 0.0067(5) 0.1055(10) 0.5999(5) 0.091(3) Uani 1 1 d . . . H2N H -0.0199 0.0494 0.6217 0.109 Uiso 1 1 calc R . . N3 N 0.1189(5) 0.5347(9) 0.7415(4) 0.073(2) Uani 1 1 d . . . N4 N 0.3880(4) 0.4887(8) 0.4076(4) 0.067(2) Uani 1 1 d . . . N5 N 0.5725(5) 0.5146(9) 0.3687(4) 0.074(2) Uani 1 1 d . . . H5N H 0.5713 0.4467 0.3374 0.089 Uiso 1 1 calc R . . N6 N 0.7002(5) 0.9214(9) 0.2519(4) 0.067(2) Uani 1 1 d . . . C1 C 0.1738(6) -0.0776(10) 0.5105(5) 0.071(3) Uani 1 1 d . . . H1 H 0.2110 -0.1202 0.4897 0.085 Uiso 1 1 calc R . . C2 C 0.1345(8) -0.1578(12) 0.5542(6) 0.093(4) Uani 1 1 d . . . H2 H 0.1462 -0.2530 0.5637 0.111 Uiso 1 1 calc R . . C3 C 0.0788(7) -0.0966(13) 0.5831(5) 0.086(4) Uani 1 1 d . . . H3 H 0.0509 -0.1513 0.6106 0.103 Uiso 1 1 calc R . . C4 C 0.0635(6) 0.0469(10) 0.5717(5) 0.068(3) Uani 1 1 d . . . C5 C 0.1057(5) 0.1197(11) 0.5285(5) 0.064(2) Uani 1 1 d . . . H5 H 0.0963 0.2162 0.5204 0.076 Uiso 1 1 calc R . . C6 C -0.0119(6) 0.2530(13) 0.5961(5) 0.084(3) Uani 1 1 d . . . H6A H -0.0608 0.2632 0.6072 0.101 Uiso 1 1 calc R . . H6B H -0.0109 0.2855 0.5468 0.101 Uiso 1 1 calc R . . C7 C 0.0360(6) 0.3485(11) 0.6462(5) 0.067(2) Uani 1 1 d . . . C8 C 0.0229(6) 0.4959(12) 0.6472(6) 0.085(3) Uani 1 1 d . . . H8 H -0.0139 0.5357 0.6154 0.101 Uiso 1 1 calc R . . C9 C 0.0651(7) 0.5819(12) 0.6958(7) 0.096(4) Uani 1 1 d . . . H9 H 0.0548 0.6790 0.6961 0.115 Uiso 1 1 calc R . . C10 C 0.1320(7) 0.3975(12) 0.7396(6) 0.085(3) Uani 1 1 d . . . H10 H 0.1709 0.3624 0.7703 0.102 Uiso 1 1 calc R . . C11 C 0.0918(7) 0.3007(12) 0.6947(6) 0.088(3) Uani 1 1 d . . . H11 H 0.1027 0.2039 0.6976 0.105 Uiso 1 1 calc R . . C12 C 0.3817(6) 0.6092(11) 0.4443(6) 0.074(3) Uani 1 1 d . . . H12 H 0.3383 0.6305 0.4610 0.089 Uiso 1 1 calc R . . C13 C 0.4386(6) 0.7033(10) 0.4579(5) 0.073(3) Uani 1 1 d . . . H13 H 0.4331 0.7856 0.4846 0.087 Uiso 1 1 calc R . . C14 C 0.5017(6) 0.6778(10) 0.4330(5) 0.067(2) Uani 1 1 d . . . H14 H 0.5389 0.7437 0.4407 0.081 Uiso 1 1 calc R . . C15 C 0.5106(6) 0.5509(9) 0.3954(5) 0.062(2) Uani 1 1 d . . . C16 C 0.4510(6) 0.4624(10) 0.3842(5) 0.067(2) Uani 1 1 d . . . H16 H 0.4553 0.3785 0.3584 0.080 Uiso 1 1 calc R . . C17 C 0.6391(6) 0.5847(11) 0.3904(5) 0.070(3) Uani 1 1 d . . . H17A H 0.6771 0.5139 0.3939 0.085 Uiso 1 1 calc R . . H17B H 0.6379 0.6241 0.4384 0.085 Uiso 1 1 calc R . . C18 C 0.6579(5) 0.7030(10) 0.3409(4) 0.060(2) Uani 1 1 d . . . C19 C 0.7121(6) 0.7966(12) 0.3636(5) 0.078(3) Uani 1 1 d . . . H19 H 0.7359 0.7886 0.4103 0.094 Uiso 1 1 calc R . . C20 C 0.7318(6) 0.9010(12) 0.3191(5) 0.079(3) Uani 1 1 d . . . H20 H 0.7694 0.9611 0.3366 0.095 Uiso 1 1 calc R . . C21 C 0.6471(6) 0.8295(11) 0.2290(5) 0.076(3) Uani 1 1 d . . . H21 H 0.6239 0.8395 0.1821 0.092 Uiso 1 1 calc R . . C22 C 0.6254(6) 0.7221(11) 0.2712(5) 0.076(3) Uani 1 1 d . . . H22 H 0.5884 0.6616 0.2525 0.091 Uiso 1 1 calc R . . O1W O 0.5393(14) 0.183(3) 0.3193(17) 0.137(13) Uani 0.45(4) 1 d P A 1 O1W' O 0.5391(15) 0.066(3) 0.3498(15) 0.170(14) Uani 0.55(4) 1 d P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0699(9) 0.0853(8) 0.0631(7) 0.0079(6) 0.0180(6) -0.0002(6) Cu2 0.0601(8) 0.0854(9) 0.0876(9) -0.0053(7) 0.0083(7) -0.0122(6) Cu3 0.0733(9) 0.0854(9) 0.0769(8) 0.0139(6) -0.0044(7) 0.0037(7) Cu4 0.0866(10) 0.0839(8) 0.0641(7) -0.0071(6) 0.0129(7) 0.0077(7) I1 0.0618(5) 0.0762(5) 0.0712(4) -0.0066(3) 0.0068(3) 0.0064(3) I2 0.0638(5) 0.0822(5) 0.0614(4) -0.0006(3) 0.0071(3) -0.0151(3) I3 0.0634(5) 0.0732(4) 0.0651(4) -0.0026(3) -0.0001(3) 0.0077(3) I4 0.0856(6) 0.0910(5) 0.0718(5) 0.0085(3) 0.0223(4) -0.0122(4) N1 0.067(6) 0.077(5) 0.056(4) 0.000(4) 0.005(4) -0.007(4) N2 0.092(7) 0.095(7) 0.094(7) -0.026(5) 0.046(6) -0.031(6) N3 0.071(6) 0.080(6) 0.064(5) 0.000(4) -0.007(4) 0.008(4) N4 0.062(6) 0.068(5) 0.071(5) 0.004(4) 0.003(4) -0.007(4) N5 0.067(6) 0.085(5) 0.072(5) -0.021(4) 0.018(4) -0.025(5) N6 0.061(5) 0.085(5) 0.057(4) 0.001(4) 0.006(4) -0.004(4) C1 0.071(7) 0.075(6) 0.067(6) 0.001(5) 0.013(5) 0.001(5) C2 0.136(12) 0.068(7) 0.073(7) 0.009(5) 0.011(8) -0.031(7) C3 0.104(10) 0.099(8) 0.057(6) 0.000(6) 0.018(6) -0.035(7) C4 0.077(7) 0.065(6) 0.064(6) -0.012(4) 0.013(5) -0.019(5) C5 0.062(6) 0.072(6) 0.059(5) -0.007(4) 0.016(5) -0.014(5) C6 0.066(7) 0.121(9) 0.067(6) -0.026(6) 0.013(5) -0.028(7) C7 0.060(6) 0.085(7) 0.058(5) -0.008(5) 0.013(5) -0.010(5) C8 0.075(8) 0.086(7) 0.088(8) 0.000(6) -0.007(6) 0.012(6) C9 0.101(10) 0.074(7) 0.102(9) -0.004(6) -0.026(8) -0.013(6) C10 0.086(8) 0.079(7) 0.080(7) -0.018(6) -0.027(6) 0.012(6) C11 0.093(9) 0.086(7) 0.078(7) -0.010(6) -0.010(6) 0.006(6) C12 0.066(7) 0.071(6) 0.082(7) -0.007(5) -0.002(5) -0.004(5) C13 0.079(8) 0.058(5) 0.078(6) -0.009(5) 0.000(5) 0.011(5) C14 0.060(6) 0.066(6) 0.076(6) -0.001(4) 0.006(5) -0.009(5) C15 0.066(6) 0.057(5) 0.062(5) 0.004(4) 0.011(5) -0.005(4) C16 0.073(7) 0.057(5) 0.070(6) -0.003(4) 0.012(5) -0.011(5) C17 0.069(7) 0.095(7) 0.048(5) -0.005(5) 0.010(5) -0.004(5) C18 0.049(5) 0.081(6) 0.052(5) -0.005(4) 0.008(4) -0.010(4) C19 0.073(7) 0.101(8) 0.059(6) 0.005(5) 0.003(5) -0.017(6) C20 0.078(8) 0.099(7) 0.056(5) 0.004(5) -0.008(5) -0.029(6) C21 0.090(8) 0.089(7) 0.047(5) 0.001(5) -0.001(5) -0.015(6) C22 0.083(8) 0.092(7) 0.050(5) -0.005(5) -0.004(5) -0.024(6) O1W 0.15(2) 0.073(17) 0.20(3) -0.007(15) 0.08(2) 0.002(13) O1W' 0.20(3) 0.14(3) 0.18(2) 0.002(17) 0.10(2) 0.009(17) _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 2.030(8) . ? Cu1 Cu3 2.645(2) . ? Cu1 Cu4 2.658(2) . ? Cu1 I3 2.6699(16) . ? Cu1 Cu2 2.674(2) . ? Cu1 I1 2.6777(15) . ? Cu1 I2 2.7759(17) . ? Cu2 N4 2.028(8) . ? Cu2 Cu3 2.618(2) . ? Cu2 I1 2.7002(16) . ? Cu2 I4 2.7193(16) . ? Cu2 I3 2.7261(16) . ? Cu2 Cu4 2.839(2) . ? Cu3 N3 2.013(9) 4_565 ? Cu3 I2 2.6502(16) . ? Cu3 I4 2.6826(17) . ? Cu3 I1 2.7209(16) . ? Cu3 Cu4 2.818(2) . ? Cu4 N6 2.042(8) 2_645 ? Cu4 I3 2.6497(17) . ? Cu4 I4 2.6592(16) . ? Cu4 I2 2.7516(17) . ? N1 C5 1.324(12) . ? N1 C1 1.348(12) . ? N2 C4 1.362(13) . ? N2 C6 1.424(15) . ? N2 H2N 0.8600 . ? N3 C10 1.310(13) . ? N3 C9 1.313(14) . ? N3 Cu3 2.013(9) 4_566 ? N4 C12 1.332(12) . ? N4 C16 1.334(12) . ? N5 C15 1.363(12) . ? N5 C17 1.426(12) . ? N5 H5N 0.8600 . ? N6 C20 1.329(12) . ? N6 C21 1.346(12) . ? N6 Cu4 2.042(8) 2_665 ? C1 C2 1.385(14) . ? C1 H1 0.9300 . ? C2 C3 1.362(17) . ? C2 H2 0.9300 . ? C3 C4 1.385(15) . ? C3 H3 0.9300 . ? C4 C5 1.377(12) . ? C5 H5 0.9300 . ? C6 C7 1.508(13) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C11 1.370(15) . ? C7 C8 1.403(14) . ? C8 C9 1.384(15) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.390(14) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.383(14) . ? C12 H12 0.9300 . ? C13 C14 1.346(14) . ? C13 H13 0.9300 . ? C14 C15 1.399(13) . ? C14 H14 0.9300 . ? C15 C16 1.388(13) . ? C16 H16 0.9300 . ? C17 C18 1.511(13) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.369(13) . ? C18 C22 1.375(12) . ? C19 C20 1.362(13) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C22 1.369(13) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 Cu3 141.7(3) . . ? N1 Cu1 Cu4 134.3(2) . . ? Cu3 Cu1 Cu4 64.21(5) . . ? N1 Cu1 I3 107.4(3) . . ? Cu3 Cu1 I3 110.19(6) . . ? Cu4 Cu1 I3 59.64(5) . . ? N1 Cu1 Cu2 152.8(2) . . ? Cu3 Cu1 Cu2 58.96(5) . . ? Cu4 Cu1 Cu2 64.33(5) . . ? I3 Cu1 Cu2 61.35(5) . . ? N1 Cu1 I1 109.1(2) . . ? Cu3 Cu1 I1 61.49(4) . . ? Cu4 Cu1 I1 116.30(5) . . ? I3 Cu1 I1 113.25(5) . . ? Cu2 Cu1 I1 60.60(4) . . ? N1 Cu1 I2 98.2(2) . . ? Cu3 Cu1 I2 58.48(5) . . ? Cu4 Cu1 I2 60.80(5) . . ? I3 Cu1 I2 116.41(5) . . ? Cu2 Cu1 I2 108.95(5) . . ? I1 Cu1 I2 111.12(5) . . ? N4 Cu2 Cu3 140.6(2) . . ? N4 Cu2 Cu1 151.3(2) . . ? Cu3 Cu2 Cu1 59.96(5) . . ? N4 Cu2 I1 107.8(2) . . ? Cu3 Cu2 I1 61.53(5) . . ? Cu1 Cu2 I1 59.77(4) . . ? N4 Cu2 I4 103.3(2) . . ? Cu3 Cu2 I4 60.31(5) . . ? Cu1 Cu2 I4 105.30(6) . . ? I1 Cu2 I4 117.99(6) . . ? N4 Cu2 I3 109.8(2) . . ? Cu3 Cu2 I3 109.28(6) . . ? Cu1 Cu2 I3 59.26(4) . . ? I1 Cu2 I3 110.77(5) . . ? I4 Cu2 I3 106.77(5) . . ? N4 Cu2 Cu4 142.4(2) . . ? Cu3 Cu2 Cu4 62.04(5) . . ? Cu1 Cu2 Cu4 57.57(5) . . ? I1 Cu2 Cu4 109.80(5) . . ? I4 Cu2 Cu4 57.12(4) . . ? I3 Cu2 Cu4 56.83(4) . . ? N3 Cu3 Cu2 134.2(3) 4_565 . ? N3 Cu3 Cu1 153.1(3) 4_565 . ? Cu2 Cu3 Cu1 61.07(5) . . ? N3 Cu3 I2 110.8(3) 4_565 . ? Cu2 Cu3 I2 114.71(6) . . ? Cu1 Cu3 I2 63.24(5) . . ? N3 Cu3 I4 99.6(3) 4_565 . ? Cu2 Cu3 I4 61.72(5) . . ? Cu1 Cu3 I4 107.18(6) . . ? I2 Cu3 I4 108.05(5) . . ? N3 Cu3 I1 105.1(2) 4_565 . ? Cu2 Cu3 I1 60.73(5) . . ? Cu1 Cu3 I1 59.85(4) . . ? I2 Cu3 I1 113.73(5) . . ? I4 Cu3 I1 118.56(6) . . ? N3 Cu3 Cu4 144.5(2) 4_565 . ? Cu2 Cu3 Cu4 62.83(5) . . ? Cu1 Cu3 Cu4 58.13(5) . . ? I2 Cu3 Cu4 60.33(5) . . ? I4 Cu3 Cu4 57.75(4) . . ? I1 Cu3 Cu4 109.80(6) . . ? N6 Cu4 I3 110.6(2) 2_645 . ? N6 Cu4 Cu1 146.2(2) 2_645 . ? I3 Cu4 Cu1 60.40(5) . . ? N6 Cu4 I4 106.1(2) 2_645 . ? I3 Cu4 I4 110.83(6) . . ? Cu1 Cu4 I4 107.47(6) . . ? N6 Cu4 I2 104.8(2) 2_645 . ? I3 Cu4 I2 117.95(6) . . ? Cu1 Cu4 I2 61.71(5) . . ? I4 Cu4 I2 105.79(5) . . ? N6 Cu4 Cu3 143.7(2) 2_645 . ? I3 Cu4 Cu3 105.66(5) . . ? Cu1 Cu4 Cu3 57.66(5) . . ? I4 Cu4 Cu3 58.56(5) . . ? I2 Cu4 Cu3 56.81(4) . . ? N6 Cu4 Cu2 149.5(2) 2_645 . ? I3 Cu4 Cu2 59.44(4) . . ? Cu1 Cu4 Cu2 58.10(5) . . ? I4 Cu4 Cu2 59.18(4) . . ? I2 Cu4 Cu2 105.01(5) . . ? Cu3 Cu4 Cu2 55.12(5) . . ? Cu1 I1 Cu2 59.63(4) . . ? Cu1 I1 Cu3 58.66(4) . . ? Cu2 I1 Cu3 57.74(5) . . ? Cu3 I2 Cu4 62.87(4) . . ? Cu3 I2 Cu1 58.29(4) . . ? Cu4 I2 Cu1 57.49(4) . . ? Cu4 I3 Cu1 59.96(5) . . ? Cu4 I3 Cu2 63.73(4) . . ? Cu1 I3 Cu2 59.40(4) . . ? Cu4 I4 Cu3 63.69(4) . . ? Cu4 I4 Cu2 63.70(4) . . ? Cu3 I4 Cu2 57.97(5) . . ? C5 N1 C1 118.4(9) . . ? C5 N1 Cu1 121.8(7) . . ? C1 N1 Cu1 119.3(7) . . ? C4 N2 C6 124.8(9) . . ? C4 N2 H2N 117.6 . . ? C6 N2 H2N 117.6 . . ? C10 N3 C9 116.4(9) . . ? C10 N3 Cu3 122.8(7) . 4_566 ? C9 N3 Cu3 120.8(7) . 4_566 ? C12 N4 C16 117.6(9) . . ? C12 N4 Cu2 123.5(7) . . ? C16 N4 Cu2 118.9(6) . . ? C15 N5 C17 122.6(8) . . ? C15 N5 H5N 118.7 . . ? C17 N5 H5N 118.7 . . ? C20 N6 C21 115.6(8) . . ? C20 N6 Cu4 120.6(7) . 2_665 ? C21 N6 Cu4 123.7(7) . 2_665 ? N1 C1 C2 120.7(11) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 119.7(11) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.2(10) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? N2 C4 C5 124.1(10) . . ? N2 C4 C3 119.3(10) . . ? C5 C4 C3 116.5(10) . . ? N1 C5 C4 124.5(9) . . ? N1 C5 H5 117.8 . . ? C4 C5 H5 117.8 . . ? N2 C6 C7 114.9(10) . . ? N2 C6 H6A 108.5 . . ? C7 C6 H6A 108.5 . . ? N2 C6 H6B 108.5 . . ? C7 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? C11 C7 C8 115.7(10) . . ? C11 C7 C6 124.2(10) . . ? C8 C7 C6 120.0(10) . . ? C9 C8 C7 119.6(11) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? N3 C9 C8 124.0(11) . . ? N3 C9 H9 118.0 . . ? C8 C9 H9 118.0 . . ? N3 C10 C11 124.5(11) . . ? N3 C10 H10 117.8 . . ? C11 C10 H10 117.8 . . ? C7 C11 C10 119.8(11) . . ? C7 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? N4 C12 C13 121.1(10) . . ? N4 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 121.1(9) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 119.2(9) . . ? C13 C14 H14 120.4 . . ? C15 C14 H14 120.4 . . ? N5 C15 C16 120.3(8) . . ? N5 C15 C14 123.8(9) . . ? C16 C15 C14 115.9(9) . . ? N4 C16 C15 124.9(9) . . ? N4 C16 H16 117.5 . . ? C15 C16 H16 117.5 . . ? N5 C17 C18 115.3(8) . . ? N5 C17 H17A 108.4 . . ? C18 C17 H17A 108.4 . . ? N5 C17 H17B 108.4 . . ? C18 C17 H17B 108.4 . . ? H17A C17 H17B 107.5 . . ? C19 C18 C22 115.6(9) . . ? C19 C18 C17 120.2(9) . . ? C22 C18 C17 124.1(9) . . ? C20 C19 C18 121.4(10) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? N6 C20 C19 123.5(10) . . ? N6 C20 H20 118.3 . . ? C19 C20 H20 118.3 . . ? N6 C21 C22 123.4(9) . . ? N6 C21 H21 118.3 . . ? C22 C21 H21 118.3 . . ? C21 C22 C18 120.6(9) . . ? C21 C22 H22 119.7 . . ? C18 C22 H22 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 Cu1 Cu2 N4 -3.2(8) . . . . ? Cu3 Cu1 Cu2 N4 143.3(5) . . . . ? Cu4 Cu1 Cu2 N4 -142.6(5) . . . . ? I3 Cu1 Cu2 N4 -74.7(5) . . . . ? I1 Cu1 Cu2 N4 70.8(5) . . . . ? I2 Cu1 Cu2 N4 174.9(5) . . . . ? N1 Cu1 Cu2 Cu3 -146.5(6) . . . . ? Cu4 Cu1 Cu2 Cu3 74.09(6) . . . . ? I3 Cu1 Cu2 Cu3 141.98(6) . . . . ? I1 Cu1 Cu2 Cu3 -72.52(5) . . . . ? I2 Cu1 Cu2 Cu3 31.59(6) . . . . ? N1 Cu1 Cu2 I1 -74.0(5) . . . . ? Cu3 Cu1 Cu2 I1 72.52(5) . . . . ? Cu4 Cu1 Cu2 I1 146.60(6) . . . . ? I3 Cu1 Cu2 I1 -145.51(5) . . . . ? I2 Cu1 Cu2 I1 104.11(6) . . . . ? N1 Cu1 Cu2 I4 172.2(5) . . . . ? Cu3 Cu1 Cu2 I4 -41.30(6) . . . . ? Cu4 Cu1 Cu2 I4 32.79(6) . . . . ? I3 Cu1 Cu2 I4 100.68(6) . . . . ? I1 Cu1 Cu2 I4 -113.82(6) . . . . ? I2 Cu1 Cu2 I4 -9.71(7) . . . . ? N1 Cu1 Cu2 I3 71.5(5) . . . . ? Cu3 Cu1 Cu2 I3 -141.98(6) . . . . ? Cu4 Cu1 Cu2 I3 -67.89(5) . . . . ? I1 Cu1 Cu2 I3 145.51(5) . . . . ? I2 Cu1 Cu2 I3 -110.38(6) . . . . ? N1 Cu1 Cu2 Cu4 139.4(6) . . . . ? Cu3 Cu1 Cu2 Cu4 -74.09(6) . . . . ? I3 Cu1 Cu2 Cu4 67.89(5) . . . . ? I1 Cu1 Cu2 Cu4 -146.60(6) . . . . ? I2 Cu1 Cu2 Cu4 -42.49(5) . . . . ? N4 Cu2 Cu3 N3 -1.0(5) . . . 4_565 ? Cu1 Cu2 Cu3 N3 152.2(3) . . . 4_565 ? I1 Cu2 Cu3 N3 82.5(3) . . . 4_565 ? I4 Cu2 Cu3 N3 -74.9(3) . . . 4_565 ? I3 Cu2 Cu3 N3 -173.7(3) . . . 4_565 ? Cu4 Cu2 Cu3 N3 -141.1(3) . . . 4_565 ? N4 Cu2 Cu3 Cu1 -153.1(4) . . . . ? I1 Cu2 Cu3 Cu1 -69.63(5) . . . . ? I4 Cu2 Cu3 Cu1 132.88(6) . . . . ? I3 Cu2 Cu3 Cu1 34.11(5) . . . . ? Cu4 Cu2 Cu3 Cu1 66.77(5) . . . . ? N4 Cu2 Cu3 I2 172.0(4) . . . . ? Cu1 Cu2 Cu3 I2 -34.84(6) . . . . ? I1 Cu2 Cu3 I2 -104.48(6) . . . . ? I4 Cu2 Cu3 I2 98.03(6) . . . . ? I3 Cu2 Cu3 I2 -0.73(8) . . . . ? Cu4 Cu2 Cu3 I2 31.92(6) . . . . ? N4 Cu2 Cu3 I4 74.0(4) . . . . ? Cu1 Cu2 Cu3 I4 -132.88(6) . . . . ? I1 Cu2 Cu3 I4 157.49(5) . . . . ? I3 Cu2 Cu3 I4 -98.76(5) . . . . ? Cu4 Cu2 Cu3 I4 -66.11(4) . . . . ? N4 Cu2 Cu3 I1 -83.5(4) . . . . ? Cu1 Cu2 Cu3 I1 69.63(5) . . . . ? I4 Cu2 Cu3 I1 -157.49(5) . . . . ? I3 Cu2 Cu3 I1 103.75(5) . . . . ? Cu4 Cu2 Cu3 I1 136.40(5) . . . . ? N4 Cu2 Cu3 Cu4 140.1(4) . . . . ? Cu1 Cu2 Cu3 Cu4 -66.77(5) . . . . ? I1 Cu2 Cu3 Cu4 -136.40(5) . . . . ? I4 Cu2 Cu3 Cu4 66.11(4) . . . . ? I3 Cu2 Cu3 Cu4 -32.65(5) . . . . ? N1 Cu1 Cu3 N3 23.8(7) . . . 4_565 ? Cu4 Cu1 Cu3 N3 153.5(6) . . . 4_565 ? I3 Cu1 Cu3 N3 -167.4(6) . . . 4_565 ? Cu2 Cu1 Cu3 N3 -132.2(6) . . . 4_565 ? I1 Cu1 Cu3 N3 -61.2(6) . . . 4_565 ? I2 Cu1 Cu3 N3 83.3(6) . . . 4_565 ? N1 Cu1 Cu3 Cu2 156.0(4) . . . . ? Cu4 Cu1 Cu3 Cu2 -74.30(6) . . . . ? I3 Cu1 Cu3 Cu2 -35.16(5) . . . . ? I1 Cu1 Cu3 Cu2 71.03(5) . . . . ? I2 Cu1 Cu3 Cu2 -144.46(6) . . . . ? N1 Cu1 Cu3 I2 -59.5(4) . . . . ? Cu4 Cu1 Cu3 I2 70.16(5) . . . . ? I3 Cu1 Cu3 I2 109.30(6) . . . . ? Cu2 Cu1 Cu3 I2 144.46(6) . . . . ? I1 Cu1 Cu3 I2 -144.51(5) . . . . ? N1 Cu1 Cu3 I4 -161.5(4) . . . . ? Cu4 Cu1 Cu3 I4 -31.80(6) . . . . ? I3 Cu1 Cu3 I4 7.33(8) . . . . ? Cu2 Cu1 Cu3 I4 42.49(6) . . . . ? I1 Cu1 Cu3 I4 113.52(6) . . . . ? I2 Cu1 Cu3 I4 -101.97(6) . . . . ? N1 Cu1 Cu3 I1 85.0(4) . . . . ? Cu4 Cu1 Cu3 I1 -145.33(6) . . . . ? I3 Cu1 Cu3 I1 -106.20(6) . . . . ? Cu2 Cu1 Cu3 I1 -71.03(5) . . . . ? I2 Cu1 Cu3 I1 144.51(5) . . . . ? N1 Cu1 Cu3 Cu4 -129.7(4) . . . . ? I3 Cu1 Cu3 Cu4 39.13(6) . . . . ? Cu2 Cu1 Cu3 Cu4 74.30(6) . . . . ? I1 Cu1 Cu3 Cu4 145.33(6) . . . . ? I2 Cu1 Cu3 Cu4 -70.16(5) . . . . ? N1 Cu1 Cu4 N6 -2.1(6) . . . 2_645 ? Cu3 Cu1 Cu4 N6 -140.3(5) . . . 2_645 ? I3 Cu1 Cu4 N6 83.0(4) . . . 2_645 ? Cu2 Cu1 Cu4 N6 153.4(5) . . . 2_645 ? I1 Cu1 Cu4 N6 -174.2(4) . . . 2_645 ? I2 Cu1 Cu4 N6 -73.6(5) . . . 2_645 ? N1 Cu1 Cu4 I3 -85.1(4) . . . . ? Cu3 Cu1 Cu4 I3 136.65(6) . . . . ? Cu2 Cu1 Cu4 I3 70.42(5) . . . . ? I1 Cu1 Cu4 I3 102.76(6) . . . . ? I2 Cu1 Cu4 I3 -156.63(5) . . . . ? N1 Cu1 Cu4 I4 170.4(3) . . . . ? Cu3 Cu1 Cu4 I4 32.17(6) . . . . ? I3 Cu1 Cu4 I4 -104.48(6) . . . . ? Cu2 Cu1 Cu4 I4 -34.05(6) . . . . ? I1 Cu1 Cu4 I4 -1.72(9) . . . . ? I2 Cu1 Cu4 I4 98.90(6) . . . . ? N1 Cu1 Cu4 I2 71.5(4) . . . . ? Cu3 Cu1 Cu4 I2 -66.73(5) . . . . ? I3 Cu1 Cu4 I2 156.63(5) . . . . ? Cu2 Cu1 Cu4 I2 -132.95(5) . . . . ? I1 Cu1 Cu4 I2 -100.61(6) . . . . ? N1 Cu1 Cu4 Cu3 138.3(4) . . . . ? I3 Cu1 Cu4 Cu3 -136.65(6) . . . . ? Cu2 Cu1 Cu4 Cu3 -66.23(6) . . . . ? I1 Cu1 Cu4 Cu3 -33.89(6) . . . . ? I2 Cu1 Cu4 Cu3 66.73(5) . . . . ? N1 Cu1 Cu4 Cu2 -155.5(4) . . . . ? Cu3 Cu1 Cu4 Cu2 66.23(6) . . . . ? I3 Cu1 Cu4 Cu2 -70.42(5) . . . . ? I1 Cu1 Cu4 Cu2 32.34(6) . . . . ? I2 Cu1 Cu4 Cu2 132.95(5) . . . . ? N3 Cu3 Cu4 N6 -16.5(6) 4_565 . . 2_645 ? Cu2 Cu3 Cu4 N6 -145.6(4) . . . 2_645 ? Cu1 Cu3 Cu4 N6 143.1(4) . . . 2_645 ? I2 Cu3 Cu4 N6 67.9(4) . . . 2_645 ? I4 Cu3 Cu4 N6 -73.4(4) . . . 2_645 ? I1 Cu3 Cu4 N6 174.6(4) . . . 2_645 ? N3 Cu3 Cu4 I3 162.1(4) 4_565 . . . ? Cu2 Cu3 Cu4 I3 32.97(5) . . . . ? Cu1 Cu3 Cu4 I3 -38.31(5) . . . . ? I2 Cu3 Cu4 I3 -113.47(6) . . . . ? I4 Cu3 Cu4 I3 105.16(6) . . . . ? I1 Cu3 Cu4 I3 -6.78(8) . . . . ? N3 Cu3 Cu4 Cu1 -159.6(5) 4_565 . . . ? Cu2 Cu3 Cu4 Cu1 71.27(6) . . . . ? I2 Cu3 Cu4 Cu1 -75.17(5) . . . . ? I4 Cu3 Cu4 Cu1 143.46(7) . . . . ? I1 Cu3 Cu4 Cu1 31.52(6) . . . . ? N3 Cu3 Cu4 I4 56.9(4) 4_565 . . . ? Cu2 Cu3 Cu4 I4 -72.19(5) . . . . ? Cu1 Cu3 Cu4 I4 -143.46(7) . . . . ? I2 Cu3 Cu4 I4 141.37(5) . . . . ? I1 Cu3 Cu4 I4 -111.94(6) . . . . ? N3 Cu3 Cu4 I2 -84.5(4) 4_565 . . . ? Cu2 Cu3 Cu4 I2 146.44(6) . . . . ? Cu1 Cu3 Cu4 I2 75.17(5) . . . . ? I4 Cu3 Cu4 I2 -141.37(5) . . . . ? I1 Cu3 Cu4 I2 106.69(6) . . . . ? N3 Cu3 Cu4 Cu2 129.1(5) 4_565 . . . ? Cu1 Cu3 Cu4 Cu2 -71.27(6) . . . . ? I2 Cu3 Cu4 Cu2 -146.44(6) . . . . ? I4 Cu3 Cu4 Cu2 72.19(5) . . . . ? I1 Cu3 Cu4 Cu2 -39.75(5) . . . . ? N4 Cu2 Cu4 N6 0.8(6) . . . 2_645 ? Cu3 Cu2 Cu4 N6 138.9(5) . . . 2_645 ? Cu1 Cu2 Cu4 N6 -150.6(5) . . . 2_645 ? I1 Cu2 Cu4 N6 179.0(5) . . . 2_645 ? I4 Cu2 Cu4 N6 67.8(5) . . . 2_645 ? I3 Cu2 Cu4 N6 -78.6(5) . . . 2_645 ? N4 Cu2 Cu4 I3 79.4(4) . . . . ? Cu3 Cu2 Cu4 I3 -142.52(6) . . . . ? Cu1 Cu2 Cu4 I3 -72.05(5) . . . . ? I1 Cu2 Cu4 I3 -102.41(6) . . . . ? I4 Cu2 Cu4 I3 146.41(6) . . . . ? N4 Cu2 Cu4 Cu1 151.4(4) . . . . ? Cu3 Cu2 Cu4 Cu1 -70.48(6) . . . . ? I1 Cu2 Cu4 Cu1 -30.36(6) . . . . ? I4 Cu2 Cu4 Cu1 -141.54(7) . . . . ? I3 Cu2 Cu4 Cu1 72.05(5) . . . . ? N4 Cu2 Cu4 I4 -67.1(4) . . . . ? Cu3 Cu2 Cu4 I4 71.06(5) . . . . ? Cu1 Cu2 Cu4 I4 141.54(7) . . . . ? I1 Cu2 Cu4 I4 111.18(7) . . . . ? I3 Cu2 Cu4 I4 -146.41(6) . . . . ? N4 Cu2 Cu4 I2 -166.7(4) . . . . ? Cu3 Cu2 Cu4 I2 -28.62(5) . . . . ? Cu1 Cu2 Cu4 I2 41.86(5) . . . . ? I1 Cu2 Cu4 I2 11.50(7) . . . . ? I4 Cu2 Cu4 I2 -99.68(6) . . . . ? I3 Cu2 Cu4 I2 113.91(6) . . . . ? N4 Cu2 Cu4 Cu3 -138.1(4) . . . . ? Cu1 Cu2 Cu4 Cu3 70.48(6) . . . . ? I1 Cu2 Cu4 Cu3 40.11(5) . . . . ? I4 Cu2 Cu4 Cu3 -71.06(5) . . . . ? I3 Cu2 Cu4 Cu3 142.52(6) . . . . ? N1 Cu1 I1 Cu2 152.3(3) . . . . ? Cu3 Cu1 I1 Cu2 -68.44(6) . . . . ? Cu4 Cu1 I1 Cu2 -33.60(7) . . . . ? I3 Cu1 I1 Cu2 32.74(5) . . . . ? I2 Cu1 I1 Cu2 -100.49(6) . . . . ? N1 Cu1 I1 Cu3 -139.2(3) . . . . ? Cu4 Cu1 I1 Cu3 34.84(7) . . . . ? I3 Cu1 I1 Cu3 101.19(6) . . . . ? Cu2 Cu1 I1 Cu3 68.44(6) . . . . ? I2 Cu1 I1 Cu3 -32.04(5) . . . . ? N4 Cu2 I1 Cu1 -151.5(2) . . . . ? Cu3 Cu2 I1 Cu1 69.94(5) . . . . ? I4 Cu2 I1 Cu1 92.07(6) . . . . ? I3 Cu2 I1 Cu1 -31.37(5) . . . . ? Cu4 Cu2 I1 Cu1 29.59(5) . . . . ? N4 Cu2 I1 Cu3 138.5(2) . . . . ? Cu1 Cu2 I1 Cu3 -69.94(5) . . . . ? I4 Cu2 I1 Cu3 22.13(5) . . . . ? I3 Cu2 I1 Cu3 -101.31(6) . . . . ? Cu4 Cu2 I1 Cu3 -40.35(5) . . . . ? N3 Cu3 I1 Cu1 155.8(3) 4_565 . . . ? Cu2 Cu3 I1 Cu1 -71.60(5) . . . . ? I2 Cu3 I1 Cu1 34.49(5) . . . . ? I4 Cu3 I1 Cu1 -94.17(7) . . . . ? Cu4 Cu3 I1 Cu1 -30.90(6) . . . . ? N3 Cu3 I1 Cu2 -132.6(3) 4_565 . . . ? Cu1 Cu3 I1 Cu2 71.60(5) . . . . ? I2 Cu3 I1 Cu2 106.09(7) . . . . ? I4 Cu3 I1 Cu2 -22.57(5) . . . . ? Cu4 Cu3 I1 Cu2 40.70(6) . . . . ? N3 Cu3 I2 Cu4 141.8(3) 4_565 . . . ? Cu2 Cu3 I2 Cu4 -32.78(6) . . . . ? Cu1 Cu3 I2 Cu4 -66.84(5) . . . . ? I4 Cu3 I2 Cu4 33.73(5) . . . . ? I1 Cu3 I2 Cu4 -100.10(7) . . . . ? N3 Cu3 I2 Cu1 -151.3(3) 4_565 . . . ? Cu2 Cu3 I2 Cu1 34.06(6) . . . . ? I4 Cu3 I2 Cu1 100.57(6) . . . . ? I1 Cu3 I2 Cu1 -33.26(5) . . . . ? Cu4 Cu3 I2 Cu1 66.84(5) . . . . ? N6 Cu4 I2 Cu3 -145.5(2) 2_645 . . . ? I3 Cu4 I2 Cu3 91.03(6) . . . . ? Cu1 Cu4 I2 Cu3 68.05(5) . . . . ? I4 Cu4 I2 Cu3 -33.61(5) . . . . ? Cu2 Cu4 I2 Cu3 28.01(5) . . . . ? N6 Cu4 I2 Cu1 146.5(2) 2_645 . . . ? I3 Cu4 I2 Cu1 22.99(5) . . . . ? I4 Cu4 I2 Cu1 -101.65(6) . . . . ? Cu3 Cu4 I2 Cu1 -68.05(5) . . . . ? Cu2 Cu4 I2 Cu1 -40.04(5) . . . . ? N1 Cu1 I2 Cu3 147.3(3) . . . . ? Cu4 Cu1 I2 Cu3 -76.00(5) . . . . ? I3 Cu1 I2 Cu3 -98.48(6) . . . . ? Cu2 Cu1 I2 Cu3 -31.78(6) . . . . ? I1 Cu1 I2 Cu3 33.15(5) . . . . ? N1 Cu1 I2 Cu4 -136.7(3) . . . . ? Cu3 Cu1 I2 Cu4 76.00(5) . . . . ? I3 Cu1 I2 Cu4 -22.47(5) . . . . ? Cu2 Cu1 I2 Cu4 44.23(6) . . . . ? I1 Cu1 I2 Cu4 109.16(6) . . . . ? N6 Cu4 I3 Cu1 -143.8(3) 2_645 . . . ? I4 Cu4 I3 Cu1 98.81(6) . . . . ? I2 Cu4 I3 Cu1 -23.30(5) . . . . ? Cu3 Cu4 I3 Cu1 37.04(5) . . . . ? Cu2 Cu4 I3 Cu1 68.26(5) . . . . ? N6 Cu4 I3 Cu2 147.9(3) 2_645 . . . ? Cu1 Cu4 I3 Cu2 -68.26(5) . . . . ? I4 Cu4 I3 Cu2 30.55(5) . . . . ? I2 Cu4 I3 Cu2 -91.56(6) . . . . ? Cu3 Cu4 I3 Cu2 -31.22(5) . . . . ? N1 Cu1 I3 Cu4 131.6(2) . . . . ? Cu3 Cu1 I3 Cu4 -41.19(6) . . . . ? Cu2 Cu1 I3 Cu4 -75.41(5) . . . . ? I1 Cu1 I3 Cu4 -107.89(6) . . . . ? I2 Cu1 I3 Cu4 22.75(5) . . . . ? N1 Cu1 I3 Cu2 -153.0(2) . . . . ? Cu3 Cu1 I3 Cu2 34.22(6) . . . . ? Cu4 Cu1 I3 Cu2 75.41(5) . . . . ? I1 Cu1 I3 Cu2 -32.48(5) . . . . ? I2 Cu1 I3 Cu2 98.15(6) . . . . ? N4 Cu2 I3 Cu4 -140.4(3) . . . . ? Cu3 Cu2 I3 Cu4 34.71(6) . . . . ? Cu1 Cu2 I3 Cu4 69.10(6) . . . . ? I1 Cu2 I3 Cu4 100.66(6) . . . . ? I4 Cu2 I3 Cu4 -29.02(5) . . . . ? N4 Cu2 I3 Cu1 150.5(3) . . . . ? Cu3 Cu2 I3 Cu1 -34.40(5) . . . . ? I1 Cu2 I3 Cu1 31.55(5) . . . . ? I4 Cu2 I3 Cu1 -98.13(6) . . . . ? Cu4 Cu2 I3 Cu1 -69.10(6) . . . . ? N6 Cu4 I4 Cu3 143.9(3) 2_645 . . . ? I3 Cu4 I4 Cu3 -96.08(6) . . . . ? Cu1 Cu4 I4 Cu3 -31.82(6) . . . . ? I2 Cu4 I4 Cu3 32.88(5) . . . . ? Cu2 Cu4 I4 Cu3 -65.44(5) . . . . ? N6 Cu4 I4 Cu2 -150.7(3) 2_645 . . . ? I3 Cu4 I4 Cu2 -30.64(5) . . . . ? Cu1 Cu4 I4 Cu2 33.61(6) . . . . ? I2 Cu4 I4 Cu2 98.32(6) . . . . ? Cu3 Cu4 I4 Cu2 65.44(5) . . . . ? N3 Cu3 I4 Cu4 -150.5(3) 4_565 . . . ? Cu2 Cu3 I4 Cu4 74.12(5) . . . . ? Cu1 Cu3 I4 Cu4 31.95(6) . . . . ? I2 Cu3 I4 Cu4 -34.78(5) . . . . ? I1 Cu3 I4 Cu4 96.47(6) . . . . ? N3 Cu3 I4 Cu2 135.4(3) 4_565 . . . ? Cu1 Cu3 I4 Cu2 -42.17(6) . . . . ? I2 Cu3 I4 Cu2 -108.90(6) . . . . ? I1 Cu3 I4 Cu2 22.35(5) . . . . ? Cu4 Cu3 I4 Cu2 -74.12(5) . . . . ? N4 Cu2 I4 Cu4 144.7(3) . . . . ? Cu3 Cu2 I4 Cu4 -74.10(5) . . . . ? Cu1 Cu2 I4 Cu4 -32.97(6) . . . . ? I1 Cu2 I4 Cu4 -96.50(6) . . . . ? I3 Cu2 I4 Cu4 28.92(5) . . . . ? N4 Cu2 I4 Cu3 -141.2(3) . . . . ? Cu1 Cu2 I4 Cu3 41.12(6) . . . . ? I1 Cu2 I4 Cu3 -22.40(5) . . . . ? I3 Cu2 I4 Cu3 103.02(6) . . . . ? Cu4 Cu2 I4 Cu3 74.10(5) . . . . ? Cu3 Cu1 N1 C5 -44.3(9) . . . . ? Cu4 Cu1 N1 C5 -149.0(6) . . . . ? I3 Cu1 N1 C5 146.7(7) . . . . ? Cu2 Cu1 N1 C5 86.0(9) . . . . ? I1 Cu1 N1 C5 23.6(8) . . . . ? I2 Cu1 N1 C5 -92.2(7) . . . . ? Cu3 Cu1 N1 C1 127.4(7) . . . . ? Cu4 Cu1 N1 C1 22.7(9) . . . . ? I3 Cu1 N1 C1 -41.6(8) . . . . ? Cu2 Cu1 N1 C1 -102.4(8) . . . . ? I1 Cu1 N1 C1 -164.8(7) . . . . ? I2 Cu1 N1 C1 79.4(8) . . . . ? Cu3 Cu2 N4 C12 65.3(9) . . . . ? Cu1 Cu2 N4 C12 -60.2(10) . . . . ? I1 Cu2 N4 C12 -1.2(8) . . . . ? I4 Cu2 N4 C12 124.4(7) . . . . ? I3 Cu2 N4 C12 -122.0(7) . . . . ? Cu4 Cu2 N4 C12 177.0(6) . . . . ? Cu3 Cu2 N4 C16 -112.7(7) . . . . ? Cu1 Cu2 N4 C16 121.8(7) . . . . ? I1 Cu2 N4 C16 -179.2(6) . . . . ? I4 Cu2 N4 C16 -53.6(7) . . . . ? I3 Cu2 N4 C16 60.0(7) . . . . ? Cu4 Cu2 N4 C16 -1.0(9) . . . . ? C5 N1 C1 C2 0.3(15) . . . . ? Cu1 N1 C1 C2 -171.6(8) . . . . ? N1 C1 C2 C3 1.8(18) . . . . ? C1 C2 C3 C4 -3.0(18) . . . . ? C6 N2 C4 C5 -7.7(17) . . . . ? C6 N2 C4 C3 175.7(10) . . . . ? C2 C3 C4 N2 178.8(11) . . . . ? C2 C3 C4 C5 2.0(16) . . . . ? C1 N1 C5 C4 -1.4(15) . . . . ? Cu1 N1 C5 C4 170.4(8) . . . . ? N2 C4 C5 N1 -176.4(10) . . . . ? C3 C4 C5 N1 0.2(15) . . . . ? C4 N2 C6 C7 -74.6(13) . . . . ? N2 C6 C7 C11 -2.7(14) . . . . ? N2 C6 C7 C8 180.0(9) . . . . ? C11 C7 C8 C9 -0.6(16) . . . . ? C6 C7 C8 C9 177.0(10) . . . . ? C10 N3 C9 C8 0.1(19) . . . . ? Cu3 N3 C9 C8 176.6(10) 4_566 . . . ? C7 C8 C9 N3 1(2) . . . . ? C9 N3 C10 C11 -2.2(18) . . . . ? Cu3 N3 C10 C11 -178.7(9) 4_566 . . . ? C8 C7 C11 C10 -1.4(16) . . . . ? C6 C7 C11 C10 -178.8(10) . . . . ? N3 C10 C11 C7 3(2) . . . . ? C16 N4 C12 C13 -0.3(14) . . . . ? Cu2 N4 C12 C13 -178.3(8) . . . . ? N4 C12 C13 C14 1.6(16) . . . . ? C12 C13 C14 C15 -2.7(15) . . . . ? C17 N5 C15 C16 -167.0(9) . . . . ? C17 N5 C15 C14 15.1(15) . . . . ? C13 C14 C15 N5 -179.4(10) . . . . ? C13 C14 C15 C16 2.5(14) . . . . ? C12 N4 C16 C15 0.3(15) . . . . ? Cu2 N4 C16 C15 178.4(8) . . . . ? N5 C15 C16 N4 -179.5(9) . . . . ? C14 C15 C16 N4 -1.4(14) . . . . ? C15 N5 C17 C18 -96.3(11) . . . . ? N5 C17 C18 C19 166.3(9) . . . . ? N5 C17 C18 C22 -16.2(14) . . . . ? C22 C18 C19 C20 0.0(16) . . . . ? C17 C18 C19 C20 177.6(11) . . . . ? C21 N6 C20 C19 -1.2(17) . . . . ? Cu4 N6 C20 C19 176.2(9) 2_665 . . . ? C18 C19 C20 N6 0.9(19) . . . . ? C20 N6 C21 C22 0.7(16) . . . . ? Cu4 N6 C21 C22 -176.7(8) 2_665 . . . ? N6 C21 C22 C18 0.1(18) . . . . ? C19 C18 C22 C21 -0.4(15) . . . . ? C17 C18 C22 C21 -177.9(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N I2 0.86 2.81 3.647(9) 165.7 3_556 N5 H5N O1W 0.86 2.55 3.27(3) 142.2 . N5 H5N I4 0.86 3.19 3.771(8) 127.0 2_655 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.010 _refine_diff_density_min -1.148 _refine_diff_density_rms 0.211 _database_code_depnum_ccdc_archive 'CCDC 934842' ####################################################################### # # 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_5 #TrackingRef 'cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H11 Cu2 I2 N3' _chemical_formula_sum 'C11 H11 Cu2 I2 N3' _chemical_formula_weight 566.11 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 monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' 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 18.5585(10) _cell_length_b 4.2800(2) _cell_length_c 19.0844(9) _cell_angle_alpha 90.00 _cell_angle_beta 108.395(5) _cell_angle_gamma 90.00 _cell_volume 1438.42(12) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 2016 _cell_measurement_theta_min 3.71 _cell_measurement_theta_max 27.44 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 7.233 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3559 _exptl_absorpt_correction_T_max 0.4100 _exptl_absorpt_process_details 'ABSCOR (Higashi, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2794 _diffrn_reflns_av_R_equivalents 0.0155 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.70 _diffrn_reflns_theta_max 27.49 _reflns_number_total 1645 _reflns_number_gt 1257 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'RAPID-AUTO (Rigaku Corporation, 1998)' _computing_cell_refinement RAPID-AUTO _computing_data_reduction 'CrystalStructure (Rigaku/MSC and Rigaku Corporation, 2002)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'ORTEP-II (Johnson, 1976)' _computing_molecular_graphics SHELXL-97 _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^)+(0.0373P)^2^+4.5842P] 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 1645 _refine_ls_number_parameters 121 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0376 _refine_ls_wR_factor_ref 0.0896 _refine_ls_wR_factor_gt 0.0804 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.041 _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 I1 I 0.59861(2) 0.69902(9) 0.57363(2) 0.05280(18) Uani 1 1 d . . . Cu1 Cu 0.55124(6) 0.2066(2) 0.48719(5) 0.0660(3) Uani 1 1 d . . . N1 N 0.5956(7) 0.142(3) 0.4070(5) 0.058(8) Uani 0.50 1 d PG A -1 C1 C 0.6635(6) 0.268(2) 0.4036(5) 0.044(3) Uani 0.50 1 d PGU A -1 H1 H 0.6916 0.4004 0.4409 0.053 Uiso 0.50 1 calc PR A -1 C2 C 0.6892(5) 0.196(3) 0.3446(6) 0.059(4) Uani 0.50 1 d PGU A -1 H2 H 0.7346 0.2804 0.3424 0.071 Uiso 0.50 1 calc PR A -1 C3 C 0.6472(6) -0.002(3) 0.2890(5) 0.058(4) Uani 0.50 1 d PGU A -1 H3 H 0.6645 -0.0504 0.2495 0.069 Uiso 0.50 1 calc PR A -1 C4 C 0.5794(5) -0.1285(19) 0.2924(4) 0.041(3) Uani 0.50 1 d PGDU A -1 C5 C 0.5536(5) -0.057(3) 0.3514(6) 0.043(4) Uani 0.50 1 d PGU A -1 H5 H 0.5082 -0.1411 0.3537 0.051 Uiso 0.50 1 calc PR A -1 C6 C 0.5324(7) -0.332(2) 0.2357(6) 0.060(3) Uani 0.25 1 d PDU A -1 H6A H 0.4960 -0.4360 0.2548 0.072 Uiso 0.25 1 calc PR A -1 H6B H 0.5643 -0.4924 0.2248 0.072 Uiso 0.25 1 calc PR A -1 N2 N 0.4912(5) -0.171(2) 0.1671(6) 0.041(2) Uani 0.25 1 d PD A -1 H2N H 0.5097 -0.1733 0.1311 0.049 Uiso 0.25 1 calc PR A -1 N6' N 0.5324(7) -0.332(2) 0.2357(6) 0.060(3) Uani 0.25 1 d P A -1 H6N' H 0.5290 -0.5304 0.2418 0.072 Uiso 0.25 1 calc PR A -1 C2' C 0.4912(5) -0.171(2) 0.1671(6) 0.041(2) Uani 0.25 1 d PU A -1 H2'A H 0.5261 -0.0202 0.1578 0.049 Uiso 0.25 1 calc PR A -1 H2'B H 0.4813 -0.3251 0.1279 0.049 Uiso 0.25 1 calc PR A -1 C7 C 0.4226(5) -0.013(2) 0.1582(5) 0.036(3) Uani 0.50 1 d PGDU A -1 C8 C 0.3808(6) -0.023(2) 0.2071(4) 0.059(4) Uani 0.50 1 d PGU A -1 H8 H 0.3988 -0.1359 0.2509 0.070 Uiso 0.50 1 calc PR A -1 C9 C 0.3121(6) 0.135(3) 0.1906(6) 0.061(4) Uani 0.50 1 d PGU A -1 H9 H 0.2841 0.1282 0.2233 0.074 Uiso 0.50 1 calc PR A -1 C10 C 0.2852(5) 0.303(2) 0.1252(6) 0.071(5) Uani 0.50 1 d PGU A -1 H10 H 0.2392 0.4089 0.1141 0.085 Uiso 0.50 1 calc PR A -1 C11 C 0.3270(6) 0.313(3) 0.0763(5) 0.068(5) Uani 0.50 1 d PGU A -1 H11 H 0.3090 0.4255 0.0325 0.082 Uiso 0.50 1 calc PR A -1 N3 N 0.3957(6) 0.155(3) 0.0928(5) 0.039(6) Uani 0.50 1 d PG . -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.0665(3) 0.0341(2) 0.0479(3) -0.00119(17) 0.00389(19) 0.00813(18) Cu1 0.0822(6) 0.0590(5) 0.0573(5) -0.0033(4) 0.0229(5) -0.0005(4) N1 0.047(11) 0.049(16) 0.067(18) 0.002(14) 0.002(10) 0.008(10) C1 0.048(7) 0.037(6) 0.035(6) 0.007(5) -0.005(5) -0.001(5) C2 0.059(7) 0.061(7) 0.060(8) 0.004(6) 0.022(6) -0.003(6) C3 0.058(8) 0.058(7) 0.062(8) 0.012(6) 0.026(6) 0.008(6) C4 0.045(6) 0.037(5) 0.037(6) 0.007(5) 0.008(5) 0.016(5) C5 0.057(8) 0.046(7) 0.038(6) 0.011(5) 0.035(6) 0.016(6) C6 0.077(7) 0.048(6) 0.052(6) 0.000(5) 0.015(5) 0.015(5) N2 0.045(5) 0.041(5) 0.034(5) -0.005(4) 0.008(4) 0.013(4) N6' 0.077(7) 0.048(6) 0.052(6) 0.000(5) 0.015(5) 0.015(5) C2' 0.045(5) 0.041(5) 0.034(5) -0.005(4) 0.008(4) 0.013(4) C7 0.027(5) 0.033(5) 0.048(7) -0.006(5) 0.010(5) 0.000(5) C8 0.058(8) 0.062(8) 0.060(7) -0.003(6) 0.026(6) -0.002(6) C9 0.055(7) 0.068(8) 0.069(8) -0.004(7) 0.032(6) 0.000(6) C10 0.068(8) 0.065(8) 0.075(8) -0.006(6) 0.016(7) 0.000(6) C11 0.060(8) 0.071(9) 0.068(9) -0.003(7) 0.011(7) -0.003(7) N3 0.050(10) 0.034(13) 0.030(11) 0.001(9) 0.009(8) 0.003(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 Cu1 2.6497(9) . ? I1 Cu1 2.6846(11) 5_666 ? I1 Cu1 2.7016(9) 1_565 ? Cu1 N1 1.973(7) . ? Cu1 N3 2.07(4) 6_656 ? Cu1 I1 2.6846(11) 5_666 ? Cu1 I1 2.7016(9) 1_545 ? Cu1 Cu1 2.751(2) 5_656 ? N1 C1 1.3900 . ? N1 C5 1.3900 . ? C1 C2 1.3900 . ? C1 H1 0.9300 . ? C2 C3 1.3900 . ? C2 H2 0.9300 . ? C3 C4 1.3900 . ? C3 H3 0.9300 . ? C4 C5 1.3900 . ? C4 C6 1.448(11) . ? C5 H5 0.9300 . ? C6 N2 1.464(15) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? N2 C7 1.403(10) . ? N2 H2N 0.8600 . ? C7 C8 1.3900 . ? C7 N3 1.3900 . ? C8 C9 1.3900 . ? C8 H8 0.9300 . ? C9 C10 1.3900 . ? C9 H9 0.9300 . ? C10 C11 1.3900 . ? C10 H10 0.9300 . ? C11 N3 1.3900 . ? C11 H11 0.9300 . ? N3 Cu1 2.073(7) 6_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag Cu1 I1 Cu1 75.85(3) . 5_666 ? Cu1 I1 Cu1 106.22(3) . 1_565 ? Cu1 I1 Cu1 61.44(3) 5_666 1_565 ? N1 Cu1 N3 3.9(6) . 6_656 ? N1 Cu1 I1 117.2(3) . . ? N3 Cu1 I1 113.7(7) 6_656 . ? N1 Cu1 I1 108.4(4) . 5_666 ? N3 Cu1 I1 111.4(3) 6_656 5_666 ? I1 Cu1 I1 104.15(3) . 5_666 ? N1 Cu1 I1 103.0(4) . 1_545 ? N3 Cu1 I1 103.0(6) 6_656 1_545 ? I1 Cu1 I1 106.22(3) . 1_545 ? I1 Cu1 I1 118.56(3) 5_666 1_545 ? N1 Cu1 Cu1 121.9(3) . 5_656 ? N3 Cu1 Cu1 125.3(7) 6_656 5_656 ? I1 Cu1 Cu1 120.85(5) . 5_656 ? I1 Cu1 Cu1 59.59(4) 5_666 5_656 ? I1 Cu1 Cu1 58.98(3) 1_545 5_656 ? C1 N1 C5 120.0 . . ? C1 N1 Cu1 125.9(6) . . ? C5 N1 Cu1 114.0(6) . . ? N1 C1 C2 120.0 . . ? N1 C1 H1 120.0 . . ? C2 C1 H1 120.0 . . ? C3 C2 C1 120.0 . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 C6 122.7(8) . . ? C5 C4 C6 117.3(8) . . ? C4 C5 N1 120.0 . . ? C4 C5 H5 120.0 . . ? N1 C5 H5 120.0 . . ? C4 C6 N2 113.9(9) . . ? C4 C6 H6A 108.8 . . ? N2 C6 H6A 108.8 . . ? C4 C6 H6B 108.8 . . ? N2 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C7 N2 C6 122.2(10) . . ? C7 N2 H2N 118.9 . . ? C6 N2 H2N 118.9 . . ? C8 C7 N3 120.0 . . ? C8 C7 N2 125.6(8) . . ? N3 C7 N2 114.4(8) . . ? C9 C8 C7 120.0 . . ? C9 C8 H8 120.0 . . ? C7 C8 H8 120.0 . . ? C8 C9 C10 120.0 . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C11 C10 C9 120.0 . . ? C11 C10 H10 120.0 . . ? C9 C10 H10 120.0 . . ? C10 C11 N3 120.0 . . ? C10 C11 H11 120.0 . . ? N3 C11 H11 120.0 . . ? C11 N3 C7 120.0 . . ? C11 N3 Cu1 113.3(6) . 6_656 ? C7 N3 Cu1 126.7(6) . 6_656 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cu1 I1 Cu1 N1 119.7(5) 5_666 . . . ? Cu1 I1 Cu1 N1 65.6(5) 1_565 . . . ? Cu1 I1 Cu1 N3 121.5(5) 5_666 . . 6_656 ? Cu1 I1 Cu1 N3 67.4(5) 1_565 . . 6_656 ? Cu1 I1 Cu1 I1 0.0 5_666 . . 5_666 ? Cu1 I1 Cu1 I1 -54.06(5) 1_565 . . 5_666 ? Cu1 I1 Cu1 I1 -125.94(5) 5_666 . . 1_545 ? Cu1 I1 Cu1 I1 180.0 1_565 . . 1_545 ? Cu1 I1 Cu1 Cu1 -62.77(5) 5_666 . . 5_656 ? Cu1 I1 Cu1 Cu1 -116.84(5) 1_565 . . 5_656 ? N3 Cu1 N1 C1 -6(10) 6_656 . . . ? I1 Cu1 N1 C1 20.1(9) . . . . ? I1 Cu1 N1 C1 137.5(6) 5_666 . . . ? I1 Cu1 N1 C1 -96.1(7) 1_545 . . . ? Cu1 Cu1 N1 C1 -157.5(5) 5_656 . . . ? N3 Cu1 N1 C5 173(11) 6_656 . . . ? I1 Cu1 N1 C5 -161.6(3) . . . . ? I1 Cu1 N1 C5 -44.2(6) 5_666 . . . ? I1 Cu1 N1 C5 82.3(5) 1_545 . . . ? Cu1 Cu1 N1 C5 20.9(7) 5_656 . . . ? C5 N1 C1 C2 0.0 . . . . ? Cu1 N1 C1 C2 178.3(10) . . . . ? N1 C1 C2 C3 0.0 . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C2 C3 C4 C6 179.0(9) . . . . ? C3 C4 C5 N1 0.0 . . . . ? C6 C4 C5 N1 -179.1(8) . . . . ? C1 N1 C5 C4 0.0 . . . . ? Cu1 N1 C5 C4 -178.5(9) . . . . ? C3 C4 C6 N2 -73.5(11) . . . . ? C5 C4 C6 N2 105.6(11) . . . . ? C4 C6 N2 C7 -82.1(14) . . . . ? C6 N2 C7 C8 -9.0(14) . . . . ? C6 N2 C7 N3 173.3(8) . . . . ? N3 C7 C8 C9 0.0 . . . . ? N2 C7 C8 C9 -177.6(9) . . . . ? C7 C8 C9 C10 0.0 . . . . ? C8 C9 C10 C11 0.0 . . . . ? C9 C10 C11 N3 0.0 . . . . ? C10 C11 N3 C7 0.0 . . . . ? C10 C11 N3 Cu1 -179.3(8) . . . 6_656 ? C8 C7 N3 C11 0.0 . . . . ? N2 C7 N3 C11 177.9(8) . . . . ? C8 C7 N3 Cu1 179.2(9) . . . 6_656 ? N2 C7 N3 Cu1 -2.9(8) . . . 6_656 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2N I1 0.86 3.03 3.672(11) 133.0 2_564 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.616 _refine_diff_density_min -0.714 _refine_diff_density_rms 0.112 _database_code_depnum_ccdc_archive 'CCDC 934843'