# 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_p1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H18 Cu2 I2 N4' _chemical_formula_weight 599.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M p2(1)/n 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 9.9100(7) _cell_length_b 16.4571(11) _cell_length_c 10.5782(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.5790(10) _cell_angle_gamma 90.00 _cell_volume 1677.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4761 _cell_measurement_theta_min 4.671 _cell_measurement_theta_max 55.281 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 6.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4559 _exptl_absorpt_correction_T_max 0.5754 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7868 _diffrn_reflns_av_R_equivalents 0.0256 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2944 _reflns_number_gt 2623 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0395P)^2^+5.6247P] 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 2944 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0849 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.20201(8) 0.36832(5) 0.50300(7) 0.0447(2) Uani 1 1 d . . . Cu2 Cu -0.07165(8) 0.44366(6) 0.34918(7) 0.0528(2) Uani 1 1 d . . . I1 I 0.06280(4) 0.39076(2) 0.58785(3) 0.03664(13) Uani 1 1 d . . . I2 I -0.33850(4) 0.39836(3) 0.27792(4) 0.05232(15) Uani 1 1 d . . . C1 C 0.2466(6) 0.4738(4) 0.2780(6) 0.0533(16) Uani 1 1 d . . . H1A H 0.2709 0.5252 0.2466 0.080 Uiso 1 1 calc R . . H1B H 0.3260 0.4385 0.2942 0.080 Uiso 1 1 calc R . . H1C H 0.2171 0.4819 0.3573 0.080 Uiso 1 1 calc R . . C2 C 0.1336(6) 0.4369(3) 0.1804(5) 0.0344(11) Uani 1 1 d . . . C3 C -0.0653(6) 0.3876(4) 0.0817(6) 0.0420(13) Uani 1 1 d . . . H3 H -0.1564 0.3690 0.0660 0.050 Uiso 1 1 calc R . . C4 C 0.0154(6) 0.3865(4) -0.0047(6) 0.0470(15) Uani 1 1 d . . . H4 H -0.0094 0.3683 -0.0903 0.056 Uiso 1 1 calc R . . C5 C 0.2600(7) 0.4290(4) 0.0006(6) 0.0477(15) Uani 1 1 d . . . H5A H 0.3373 0.4512 0.0652 0.057 Uiso 1 1 calc R . . H5B H 0.2350 0.4681 -0.0695 0.057 Uiso 1 1 calc R . . C6 C 0.3056(6) 0.3520(4) -0.0519(6) 0.0446(14) Uani 1 1 d . . . H6A H 0.2286 0.3301 -0.1172 0.054 Uiso 1 1 calc R . . H6B H 0.3295 0.3126 0.0180 0.054 Uiso 1 1 calc R . . C7 C 0.4288(6) 0.3633(4) -0.1117(6) 0.0445(14) Uani 1 1 d . . . H7A H 0.4142 0.4107 -0.1679 0.053 Uiso 1 1 calc R . . H7B H 0.5119 0.3723 -0.0436 0.053 Uiso 1 1 calc R . . C8 C 0.4478(6) 0.2896(3) -0.1890(6) 0.0412(13) Uani 1 1 d . . . H8A H 0.4520 0.2419 -0.1344 0.049 Uiso 1 1 calc R . . H8B H 0.3675 0.2839 -0.2613 0.049 Uiso 1 1 calc R . . C9 C 0.4751(6) 0.3754(5) -0.4356(6) 0.0541(17) Uani 1 1 d . . . H9A H 0.4699 0.4292 -0.4019 0.081 Uiso 1 1 calc R . . H9B H 0.3882 0.3481 -0.4423 0.081 Uiso 1 1 calc R . . H9C H 0.4947 0.3788 -0.5201 0.081 Uiso 1 1 calc R . . C10 C 0.5858(5) 0.3300(3) -0.3481(5) 0.0323(11) Uani 1 1 d . . . C11 C 0.7842(6) 0.2754(3) -0.2591(5) 0.0386(12) Uani 1 1 d . . . H11 H 0.8765 0.2594 -0.2443 0.046 Uiso 1 1 calc R . . C12 C 0.6988(6) 0.2578(4) -0.1824(6) 0.0428(13) Uani 1 1 d . . . H12 H 0.7200 0.2280 -0.1056 0.051 Uiso 1 1 calc R . . N1 N 0.0084(5) 0.4204(3) 0.1965(4) 0.0338(10) Uani 1 1 d . . . N2 N 0.1427(5) 0.4179(3) 0.0596(4) 0.0380(11) Uani 1 1 d . . . N3 N 0.5731(4) 0.2927(3) -0.2396(4) 0.0348(10) Uani 1 1 d . . . N4 N 0.7148(4) 0.3208(3) -0.3633(4) 0.0341(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0426(4) 0.0533(4) 0.0438(4) 0.0015(3) 0.0211(3) 0.0012(3) Cu2 0.0443(4) 0.0781(6) 0.0420(4) -0.0046(4) 0.0222(4) -0.0027(4) I1 0.0296(2) 0.0463(2) 0.0346(2) 0.00016(14) 0.00877(15) 0.00192(14) I2 0.0345(2) 0.0769(3) 0.0470(3) 0.0080(2) 0.01259(18) 0.00029(19) C1 0.040(3) 0.070(4) 0.048(4) -0.016(3) 0.008(3) -0.002(3) C2 0.036(3) 0.035(3) 0.036(3) 0.000(2) 0.015(2) 0.004(2) C3 0.031(3) 0.052(3) 0.043(3) -0.009(3) 0.010(3) -0.002(2) C4 0.040(3) 0.065(4) 0.038(3) -0.016(3) 0.012(3) -0.002(3) C5 0.048(4) 0.053(4) 0.053(4) -0.007(3) 0.035(3) -0.005(3) C6 0.050(4) 0.045(3) 0.049(3) 0.007(3) 0.032(3) 0.006(3) C7 0.048(4) 0.045(3) 0.048(3) 0.002(3) 0.027(3) 0.002(3) C8 0.044(3) 0.043(3) 0.048(3) 0.003(3) 0.034(3) 0.000(2) C9 0.032(3) 0.089(5) 0.045(3) 0.014(3) 0.016(3) 0.008(3) C10 0.030(3) 0.036(3) 0.034(3) -0.003(2) 0.012(2) -0.004(2) C11 0.031(3) 0.045(3) 0.041(3) -0.002(2) 0.010(2) 0.005(2) C12 0.043(3) 0.047(3) 0.040(3) 0.010(3) 0.013(3) 0.011(3) N1 0.033(2) 0.041(2) 0.031(2) 0.0029(19) 0.0146(19) 0.0063(19) N2 0.041(3) 0.043(3) 0.037(3) -0.005(2) 0.022(2) 0.000(2) N3 0.035(2) 0.035(2) 0.040(2) -0.0008(19) 0.020(2) -0.0002(19) N4 0.029(2) 0.040(2) 0.037(2) -0.0003(19) 0.0142(19) -0.0011(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N4 1.959(4) 1_456 ? Cu1 I2 2.4961(9) . ? Cu1 I1 2.5928(8) . ? Cu1 Cu2 2.6154(10) . ? Cu2 N1 1.996(4) . ? Cu2 I2 2.6797(9) . ? Cu2 I1 2.7070(9) . ? Cu2 I1 2.8018(10) 3_566 ? I1 Cu2 2.8018(10) 3_566 ? C1 C2 1.466(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.319(7) . ? C2 N2 1.340(6) . ? C3 C4 1.349(8) . ? C3 N1 1.373(7) . ? C3 H3 0.9300 . ? C4 N2 1.385(8) . ? C4 H4 0.9300 . ? C5 N2 1.454(7) . ? C5 C6 1.494(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.514(7) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.499(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N3 1.464(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.464(8) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N3 1.333(7) . ? C10 N4 1.334(6) . ? C11 C12 1.335(8) . ? C11 N4 1.375(7) . ? C11 H11 0.9300 . ? C12 N3 1.376(7) . ? C12 H12 0.9300 . ? N4 Cu1 1.959(4) 1_654 ? 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 N4 Cu1 I2 122.81(13) 1_456 . ? N4 Cu1 I1 111.73(13) 1_456 . ? I2 Cu1 I1 125.44(3) . . ? N4 Cu1 Cu2 172.43(14) 1_456 . ? I2 Cu1 Cu2 63.19(3) . . ? I1 Cu1 Cu2 62.63(3) . . ? N1 Cu2 Cu1 139.52(14) . . ? N1 Cu2 I2 105.82(14) . . ? Cu1 Cu2 I2 56.23(2) . . ? N1 Cu2 I1 119.39(13) . . ? Cu1 Cu2 I1 58.28(3) . . ? I2 Cu2 I1 114.20(3) . . ? N1 Cu2 I1 112.48(14) . 3_566 ? Cu1 Cu2 I1 107.79(3) . 3_566 ? I2 Cu2 I1 108.13(3) . 3_566 ? I1 Cu2 I1 96.31(3) . 3_566 ? Cu1 I1 Cu2 59.09(2) . . ? Cu1 I1 Cu2 101.16(3) . 3_566 ? Cu2 I1 Cu2 83.69(3) . 3_566 ? Cu1 I2 Cu2 60.58(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 110.6(5) . . ? N1 C2 C1 125.5(5) . . ? N2 C2 C1 123.9(5) . . ? C4 C3 N1 109.1(5) . . ? C4 C3 H3 125.4 . . ? N1 C3 H3 125.4 . . ? C3 C4 N2 106.2(5) . . ? C3 C4 H4 126.9 . . ? N2 C4 H4 126.9 . . ? N2 C5 C6 113.3(5) . . ? N2 C5 H5A 108.9 . . ? C6 C5 H5A 108.9 . . ? N2 C5 H5B 108.9 . . ? C6 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? C5 C6 C7 113.3(5) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 110.2(5) . . ? C8 C7 H7A 109.6 . . ? C6 C7 H7A 109.6 . . ? C8 C7 H7B 109.6 . . ? C6 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? N3 C8 C7 113.4(5) . . ? N3 C8 H8A 108.9 . . ? C7 C8 H8A 108.9 . . ? N3 C8 H8B 108.9 . . ? C7 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N4 109.8(5) . . ? N3 C10 C9 124.8(5) . . ? N4 C10 C9 125.3(5) . . ? C12 C11 N4 109.7(5) . . ? C12 C11 H11 125.2 . . ? N4 C11 H11 125.2 . . ? C11 C12 N3 106.2(5) . . ? C11 C12 H12 126.9 . . ? N3 C12 H12 126.9 . . ? C2 N1 C3 106.7(4) . . ? C2 N1 Cu2 129.0(4) . . ? C3 N1 Cu2 124.1(4) . . ? C2 N2 C4 107.3(5) . . ? C2 N2 C5 128.3(5) . . ? C4 N2 C5 124.3(5) . . ? C10 N3 C12 108.2(4) . . ? C10 N3 C8 126.2(5) . . ? C12 N3 C8 125.6(5) . . ? C10 N4 C11 106.1(4) . . ? C10 N4 Cu1 128.3(4) . 1_654 ? C11 N4 Cu1 125.4(3) . 1_654 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.984 _refine_diff_density_min -0.955 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 921645' ####################################################################### # # 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_p2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H9 Cu2 I2 N2' _chemical_formula_weight 490.03 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.2896(9) _cell_length_b 10.405(2) _cell_length_c 12.346(3) _cell_angle_alpha 110.327(3) _cell_angle_beta 95.585(3) _cell_angle_gamma 92.300(3) _cell_volume 512.66(19) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.174 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 446 _exptl_absorpt_coefficient_mu 10.117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2368 _exptl_absorpt_correction_T_max 0.4311 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2534 _diffrn_reflns_av_R_equivalents 0.0107 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1775 _reflns_number_gt 1587 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0586P)^2^+0.4369P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1775 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0852 _refine_ls_wR_factor_gt 0.0813 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5277(2) 0.12176(8) 0.84258(7) 0.0349(2) Uani 1 1 d . . . Cu2 Cu 0.0138(2) 0.06160(8) 1.14610(7) 0.0320(2) Uani 1 1 d . . . I1 I 0.03580(8) 0.19675(4) 0.99751(3) 0.02064(15) Uani 1 1 d . . . I2 I 0.43521(9) -0.13729(4) 0.71767(3) 0.02225(15) Uani 1 1 d . . . C1 C 0.0633(16) 0.1569(6) 0.6083(5) 0.0311(15) Uani 1 1 d . . . H1A H -0.1610 0.1530 0.6174 0.047 Uiso 1 1 calc R . . H1B H 0.1520 0.0736 0.6135 0.047 Uiso 1 1 calc R . . H1C H 0.0901 0.1633 0.5324 0.047 Uiso 1 1 calc R . . C2 C 0.2263(14) 0.2782(6) 0.7010(5) 0.0227(13) Uani 1 1 d . . . C3 C 0.5389(14) 0.4109(6) 0.8508(5) 0.0220(13) Uani 1 1 d . . . H3 H 0.6953 0.4406 0.9162 0.026 Uiso 1 1 calc R . . C4 C 0.3766(13) 0.4942(6) 0.8080(5) 0.0211(12) Uani 1 1 d . . . H4 H 0.3953 0.5919 0.8372 0.025 Uiso 1 1 calc R . . C5 C -0.0392(14) 0.4569(6) 0.6388(5) 0.0236(13) Uani 1 1 d . . . H5A H -0.1102 0.5466 0.6855 0.028 Uiso 1 1 calc R . . H5B H -0.2263 0.3903 0.6089 0.028 Uiso 1 1 calc R . . C6 C 0.1108(13) 0.4718(6) 0.5367(5) 0.0195(12) Uani 1 1 d . . . H6A H 0.3044 0.5345 0.5664 0.023 Uiso 1 1 calc R . . H6B H 0.1709 0.3810 0.4875 0.023 Uiso 1 1 calc R . . N1 N 0.4431(12) 0.2756(5) 0.7851(4) 0.0208(10) Uani 1 1 d . . . N2 N 0.1786(11) 0.4098(5) 0.7136(4) 0.0190(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0485(6) 0.0222(4) 0.0326(5) 0.0126(4) -0.0117(4) 0.0025(4) Cu2 0.0340(5) 0.0311(5) 0.0308(4) 0.0106(4) 0.0031(4) 0.0051(4) I1 0.0208(3) 0.0211(2) 0.0198(2) 0.00741(17) 0.00043(16) 0.00261(16) I2 0.0214(3) 0.0208(2) 0.0225(2) 0.00530(17) 0.00089(16) 0.00299(16) C1 0.037(4) 0.025(3) 0.026(3) 0.005(3) -0.009(3) 0.005(3) C2 0.026(3) 0.020(3) 0.026(3) 0.011(2) 0.007(3) 0.007(2) C3 0.025(3) 0.024(3) 0.014(3) 0.003(2) -0.001(2) -0.002(2) C4 0.027(3) 0.018(3) 0.014(3) 0.001(2) 0.001(2) 0.000(2) C5 0.020(3) 0.031(3) 0.027(3) 0.018(3) 0.005(2) 0.005(2) C6 0.019(3) 0.021(3) 0.021(3) 0.010(2) 0.000(2) 0.005(2) N1 0.030(3) 0.018(2) 0.014(2) 0.0061(19) -0.003(2) 0.003(2) N2 0.020(3) 0.019(2) 0.019(2) 0.007(2) 0.0019(19) 0.0064(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.996(5) . ? Cu1 I2 2.5900(10) . ? Cu1 I1 2.6519(10) 1_655 ? Cu1 Cu2 2.8214(13) 2_657 ? Cu1 I1 2.9328(11) . ? Cu1 Cu2 2.9915(14) 2_557 ? Cu2 I1 2.6428(10) 2_557 ? Cu2 I2 2.6440(10) 2_557 ? Cu2 I1 2.6771(10) . ? Cu2 I2 2.6817(10) 2_657 ? Cu2 Cu1 2.8214(13) 2_657 ? Cu2 Cu1 2.9915(14) 2_557 ? I1 Cu2 2.6428(10) 2_557 ? I1 Cu1 2.6519(10) 1_455 ? I2 Cu2 2.6440(10) 2_557 ? I2 Cu2 2.6817(10) 2_657 ? C1 C2 1.470(8) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.333(7) . ? C2 N2 1.350(7) . ? C3 C4 1.346(8) . ? C3 N1 1.380(7) . ? C3 H3 0.9500 . ? C4 N2 1.374(7) . ? C4 H4 0.9500 . ? C5 N2 1.466(7) . ? C5 C6 1.521(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C6 1.521(11) 2_566 ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 I2 125.18(14) . . ? N1 Cu1 I1 108.53(14) . 1_655 ? I2 Cu1 I1 116.45(3) . 1_655 ? N1 Cu1 Cu2 141.86(15) . 2_657 ? I2 Cu1 Cu2 59.23(3) . 2_657 ? I1 Cu1 Cu2 57.65(3) 1_655 2_657 ? N1 Cu1 I1 91.42(14) . . ? I2 Cu1 I1 108.93(3) . . ? I1 Cu1 I1 100.25(3) 1_655 . ? Cu2 Cu1 I1 124.63(4) 2_657 . ? N1 Cu1 Cu2 118.97(15) . 2_557 ? I2 Cu1 Cu2 55.99(3) . 2_557 ? I1 Cu1 Cu2 123.79(4) 1_655 2_557 ? Cu2 Cu1 Cu2 95.07(4) 2_657 2_557 ? I1 Cu1 Cu2 52.98(3) . 2_557 ? I1 Cu2 I2 116.63(3) 2_557 2_557 ? I1 Cu2 I1 101.36(3) 2_557 . ? I2 Cu2 I1 112.71(3) 2_557 . ? I1 Cu2 I2 113.64(3) 2_557 2_657 ? I2 Cu2 I2 107.31(3) 2_557 2_657 ? I1 Cu2 I2 104.56(3) . 2_657 ? I1 Cu2 Cu1 57.96(3) 2_557 2_657 ? I2 Cu2 Cu1 126.95(4) 2_557 2_657 ? I1 Cu2 Cu1 120.14(4) . 2_657 ? I2 Cu2 Cu1 56.08(3) 2_657 2_657 ? I1 Cu2 Cu1 62.37(3) 2_557 2_557 ? I2 Cu2 Cu1 54.30(3) 2_557 2_557 ? I1 Cu2 Cu1 126.12(4) . 2_557 ? I2 Cu2 Cu1 129.28(4) 2_657 2_557 ? Cu1 Cu2 Cu1 95.07(4) 2_657 2_557 ? Cu2 I1 Cu1 64.40(3) 2_557 1_455 ? Cu2 I1 Cu2 78.64(3) 2_557 . ? Cu1 I1 Cu2 109.74(3) 1_455 . ? Cu2 I1 Cu1 64.65(3) 2_557 . ? Cu1 I1 Cu1 100.25(3) 1_455 . ? Cu2 I1 Cu1 115.06(3) . . ? Cu1 I2 Cu2 69.71(3) . 2_557 ? Cu1 I2 Cu2 64.69(3) . 2_657 ? Cu2 I2 Cu2 107.31(3) 2_557 2_657 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 109.6(5) . . ? N1 C2 C1 125.5(5) . . ? N2 C2 C1 124.9(5) . . ? C4 C3 N1 109.5(5) . . ? C4 C3 H3 125.2 . . ? N1 C3 H3 125.2 . . ? C3 C4 N2 106.3(5) . . ? C3 C4 H4 126.9 . . ? N2 C4 H4 126.9 . . ? N2 C5 C6 112.1(5) . . ? N2 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N2 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C6 C6 C5 111.8(6) 2_566 . ? C6 C6 H6A 109.3 2_566 . ? C5 C6 H6A 109.3 . . ? C6 C6 H6B 109.3 2_566 . ? C5 C6 H6B 109.3 . . ? H6A C6 H6B 107.9 . . ? C2 N1 C3 106.4(5) . . ? C2 N1 Cu1 128.7(4) . . ? C3 N1 Cu1 122.4(4) . . ? C2 N2 C4 108.2(5) . . ? C2 N2 C5 126.7(5) . . ? C4 N2 C5 125.1(5) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 2.163 _refine_diff_density_min -0.866 _refine_diff_density_rms 0.209 _database_code_depnum_ccdc_archive 'CCDC 921646' ####################################################################### # # 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_p3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 Cu3 I3 N6' _chemical_formula_weight 898.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.3645(8) _cell_length_b 10.7637(9) _cell_length_c 12.0346(10) _cell_angle_alpha 106.9346(12) _cell_angle_beta 90.3554(13) _cell_angle_gamma 101.8012(11) _cell_volume 1254.11(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 846 _exptl_absorpt_coefficient_mu 6.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4550 _exptl_absorpt_correction_T_max 0.5746 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6288 _diffrn_reflns_av_R_equivalents 0.0179 _diffrn_reflns_av_sigmaI/netI 0.0371 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4372 _reflns_number_gt 3652 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0322P)^2^+0.5600P] 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 4372 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0399 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0716 _refine_ls_wR_factor_gt 0.0667 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.69874(7) -0.60537(7) 0.19986(6) 0.04762(19) Uani 1 1 d . . . Cu2 Cu -0.08300(7) 0.51731(7) 0.40022(7) 0.0542(2) Uani 1 1 d . . . Cu3 Cu -0.17000(7) 0.23536(7) 0.26129(7) 0.0513(2) Uani 1 1 d . . . I1 I 0.57356(4) -0.83989(4) 0.18529(4) 0.05179(13) Uani 1 1 d . . . I2 I -0.15293(3) 0.32128(3) 0.49459(3) 0.03935(11) Uani 1 1 d . . . I3 I -0.04570(3) 0.43790(3) 0.17169(3) 0.03909(11) Uani 1 1 d . . . C1 C 0.3800(6) -0.5467(7) 0.2197(6) 0.0623(18) Uani 1 1 d . . . H1A H 0.3165 -0.6025 0.1578 0.093 Uiso 1 1 calc R . . H1B H 0.3368 -0.4903 0.2775 0.093 Uiso 1 1 calc R . . H1C H 0.4193 -0.6011 0.2544 0.093 Uiso 1 1 calc R . . C2 C 0.4837(5) -0.4639(5) 0.1727(5) 0.0402(13) Uani 1 1 d . . . C3 C 0.6684(5) -0.3766(6) 0.1192(5) 0.0485(15) Uani 1 1 d . . . H3 H 0.7575 -0.3585 0.1055 0.058 Uiso 1 1 calc R . . C4 C 0.5790(5) -0.3120(6) 0.0939(6) 0.0532(16) Uani 1 1 d . . . H4 H 0.5941 -0.2435 0.0599 0.064 Uiso 1 1 calc R . . C5 C 0.3365(6) -0.3269(6) 0.1172(6) 0.0609(18) Uani 1 1 d . . . H5A H 0.2634 -0.4006 0.1139 0.073 Uiso 1 1 calc R . . H5B H 0.3317 -0.3047 0.0450 0.073 Uiso 1 1 calc R . . C6 C 0.3238(6) -0.2102(6) 0.2161(6) 0.0612(17) Uani 1 1 d . . . H6A H 0.3945 -0.1355 0.2167 0.073 Uiso 1 1 calc R . . H6B H 0.3340 -0.2310 0.2885 0.073 Uiso 1 1 calc R . . C7 C 0.1915(6) -0.1699(6) 0.2105(6) 0.0573(17) Uani 1 1 d . . . H7A H 0.1215 -0.2494 0.1914 0.069 Uiso 1 1 calc R . . H7B H 0.1779 -0.1144 0.2871 0.069 Uiso 1 1 calc R . . C8 C 0.1796(5) -0.0957(6) 0.1230(5) 0.0465(14) Uani 1 1 d . . . H8A H 0.2544 -0.0211 0.1360 0.056 Uiso 1 1 calc R . . H8B H 0.1811 -0.1543 0.0449 0.056 Uiso 1 1 calc R . . C9 C 0.1412(6) 0.1728(6) 0.2828(5) 0.0601(17) Uani 1 1 d . . . H9A H 0.2053 0.2105 0.2378 0.090 Uiso 1 1 calc R . . H9B H 0.1837 0.1335 0.3308 0.090 Uiso 1 1 calc R . . H9C H 0.1023 0.2414 0.3313 0.090 Uiso 1 1 calc R . . C10 C 0.0368(5) 0.0693(5) 0.2034(4) 0.0354(12) Uani 1 1 d . . . C11 C -0.0622(5) -0.1141(5) 0.0716(5) 0.0433(13) Uani 1 1 d . . . H11 H -0.0787 -0.1974 0.0161 0.052 Uiso 1 1 calc R . . C12 C -0.1495(5) -0.0368(5) 0.1068(5) 0.0386(12) Uani 1 1 d . . . H12 H -0.2378 -0.0582 0.0794 0.046 Uiso 1 1 calc R . . C13 C -0.1118(5) 0.8214(6) 0.3642(5) 0.0465(14) Uani 1 1 d . . . H13A H -0.1485 0.8497 0.3047 0.070 Uiso 1 1 calc R . . H13B H -0.0506 0.7670 0.3313 0.070 Uiso 1 1 calc R . . H13C H -0.0666 0.8979 0.4251 0.070 Uiso 1 1 calc R . . C14 C -0.2202(5) 0.7429(5) 0.4129(4) 0.0326(11) Uani 1 1 d . . . C15 C -0.3381(5) 0.5929(5) 0.4761(5) 0.0396(13) Uani 1 1 d . . . H15 H -0.3651 0.5154 0.4970 0.047 Uiso 1 1 calc R . . C16 C -0.4092(5) 0.6867(5) 0.4868(5) 0.0463(15) Uani 1 1 d . . . H16 H -0.4924 0.6865 0.5153 0.056 Uiso 1 1 calc R . . C17 C -0.3667(5) 0.9046(5) 0.4380(6) 0.0481(15) Uani 1 1 d . . . H17A H -0.3865 0.8955 0.3567 0.058 Uiso 1 1 calc R . . H17B H -0.2914 0.9781 0.4669 0.058 Uiso 1 1 calc R . . C18 C -0.4822(5) 0.9350(5) 0.5047(5) 0.0429(13) Uani 1 1 d . . . H18A H -0.4626 0.9439 0.5860 0.052 Uiso 1 1 calc R . . H18B H -0.5577 0.8617 0.4756 0.052 Uiso 1 1 calc R . . N1 N 0.6098(4) -0.4724(4) 0.1677(4) 0.0407(11) Uani 1 1 d . . . N2 N 0.4618(4) -0.3679(4) 0.1285(4) 0.0465(12) Uani 1 1 d . . . N3 N -0.0882(4) 0.0797(4) 0.1899(4) 0.0379(10) Uani 1 1 d . . . N4 N 0.0566(4) -0.0470(4) 0.1333(4) 0.0377(10) Uani 1 1 d . . . N5 N -0.2204(4) 0.6272(4) 0.4301(4) 0.0349(10) Uani 1 1 d . . . N6 N -0.3327(4) 0.7830(4) 0.4468(4) 0.0371(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0420(4) 0.0540(5) 0.0558(5) 0.0247(4) 0.0060(3) 0.0182(3) Cu2 0.0505(4) 0.0516(5) 0.0726(5) 0.0263(4) 0.0218(4) 0.0260(4) Cu3 0.0491(4) 0.0477(4) 0.0590(5) 0.0104(4) 0.0042(4) 0.0225(3) I1 0.0360(2) 0.0528(3) 0.0680(3) 0.0233(2) 0.00186(18) 0.00515(17) I2 0.0382(2) 0.0409(2) 0.0415(2) 0.01684(17) 0.00326(15) 0.00768(16) I3 0.03555(19) 0.0375(2) 0.0432(2) 0.00979(16) 0.00792(15) 0.00878(15) C1 0.040(3) 0.078(5) 0.080(5) 0.036(4) 0.023(3) 0.021(3) C2 0.033(3) 0.042(3) 0.048(3) 0.012(3) 0.007(2) 0.017(2) C3 0.036(3) 0.045(3) 0.066(4) 0.020(3) 0.002(3) 0.007(3) C4 0.043(3) 0.046(4) 0.074(5) 0.025(3) 0.001(3) 0.008(3) C5 0.046(4) 0.058(4) 0.078(5) 0.009(4) -0.003(3) 0.026(3) C6 0.057(4) 0.060(4) 0.068(4) 0.012(4) 0.001(3) 0.026(3) C7 0.053(4) 0.052(4) 0.079(5) 0.027(3) 0.016(3) 0.028(3) C8 0.044(3) 0.049(3) 0.047(3) 0.007(3) 0.017(3) 0.022(3) C9 0.047(4) 0.062(4) 0.060(4) 0.000(3) -0.005(3) 0.012(3) C10 0.037(3) 0.034(3) 0.036(3) 0.011(2) 0.007(2) 0.009(2) C11 0.052(3) 0.028(3) 0.045(3) 0.007(3) 0.002(3) 0.004(3) C12 0.039(3) 0.032(3) 0.043(3) 0.011(3) 0.000(2) 0.004(2) C13 0.040(3) 0.052(4) 0.058(4) 0.028(3) 0.015(3) 0.016(3) C14 0.033(3) 0.034(3) 0.032(3) 0.012(2) 0.002(2) 0.007(2) C15 0.038(3) 0.029(3) 0.055(4) 0.015(3) 0.013(3) 0.010(2) C16 0.032(3) 0.036(3) 0.076(4) 0.025(3) 0.022(3) 0.008(2) C17 0.044(3) 0.037(3) 0.072(4) 0.026(3) 0.015(3) 0.014(3) C18 0.043(3) 0.041(3) 0.053(4) 0.020(3) 0.006(3) 0.018(3) N1 0.031(2) 0.047(3) 0.044(3) 0.011(2) 0.001(2) 0.013(2) N2 0.035(2) 0.037(3) 0.067(3) 0.009(2) -0.003(2) 0.015(2) N3 0.036(2) 0.039(3) 0.040(3) 0.013(2) 0.003(2) 0.010(2) N4 0.039(2) 0.039(3) 0.039(3) 0.014(2) 0.011(2) 0.013(2) N5 0.033(2) 0.031(2) 0.041(3) 0.007(2) 0.0063(19) 0.0113(19) N6 0.030(2) 0.034(2) 0.051(3) 0.015(2) 0.009(2) 0.0118(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.976(4) . ? Cu1 I1 2.5467(8) . ? Cu1 I3 2.6356(8) 1_645 ? Cu1 Cu3 2.6488(10) 1_645 ? Cu2 N5 2.001(4) . ? Cu2 I2 2.6548(8) . ? Cu2 I3 2.6876(9) . ? Cu2 I2 2.7464(9) 2_566 ? Cu2 Cu3 2.9538(11) . ? Cu3 N3 2.004(4) . ? Cu3 Cu1 2.6488(10) 1_465 ? Cu3 I2 2.6802(9) . ? Cu3 I1 2.6860(8) 1_465 ? Cu3 I3 2.7952(8) . ? I1 Cu3 2.6860(8) 1_645 ? I2 Cu2 2.7464(9) 2_566 ? I3 Cu1 2.6356(8) 1_465 ? C1 C2 1.476(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.330(6) . ? C2 N2 1.348(6) . ? C3 C4 1.348(8) . ? C3 N1 1.368(7) . ? C3 H3 0.9300 . ? C4 N2 1.366(7) . ? C4 H4 0.9300 . ? C5 N2 1.471(7) . ? C5 C6 1.487(8) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(8) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.514(8) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N4 1.467(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.483(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 N3 1.336(6) . ? C10 N4 1.347(6) . ? C11 C12 1.341(7) . ? C11 N4 1.379(7) . ? C11 H11 0.9300 . ? C12 N3 1.382(6) . ? C12 H12 0.9300 . ? C13 C14 1.493(7) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N5 1.320(6) . ? C14 N6 1.350(6) . ? C15 C16 1.345(7) . ? C15 N5 1.368(6) . ? C15 H15 0.9300 . ? C16 N6 1.376(6) . ? C16 H16 0.9300 . ? C17 N6 1.455(6) . ? C17 C18 1.485(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C18 1.552(9) 2_476 ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? 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 I1 121.92(13) . . ? N1 Cu1 I3 114.18(13) . 1_645 ? I1 Cu1 I3 119.32(3) . 1_645 ? N1 Cu1 Cu3 174.31(13) . 1_645 ? I1 Cu1 Cu3 62.22(2) . 1_645 ? I3 Cu1 Cu3 63.87(2) 1_645 1_645 ? N5 Cu2 I2 108.12(12) . . ? N5 Cu2 I3 110.49(12) . . ? I2 Cu2 I3 114.71(3) . . ? N5 Cu2 I2 107.69(12) . 2_566 ? I2 Cu2 I2 110.02(3) . 2_566 ? I3 Cu2 I2 105.61(3) . 2_566 ? N5 Cu2 Cu3 117.09(12) . . ? I2 Cu2 Cu3 56.79(2) . . ? I3 Cu2 Cu3 59.18(2) . . ? I2 Cu2 Cu3 135.22(3) 2_566 . ? N3 Cu3 Cu1 140.38(13) . 1_465 ? N3 Cu3 I2 115.64(12) . . ? Cu1 Cu3 I2 103.97(3) 1_465 . ? N3 Cu3 I1 106.61(12) . 1_465 ? Cu1 Cu3 I1 57.02(2) 1_465 1_465 ? I2 Cu3 I1 108.63(3) . 1_465 ? N3 Cu3 I3 105.94(12) . . ? Cu1 Cu3 I3 57.84(2) 1_465 . ? I2 Cu3 I3 110.47(3) . . ? I1 Cu3 I3 109.36(3) 1_465 . ? N3 Cu3 Cu2 138.06(12) . . ? Cu1 Cu3 Cu2 66.62(3) 1_465 . ? I2 Cu3 Cu2 55.97(2) . . ? I1 Cu3 Cu2 114.97(3) 1_465 . ? I3 Cu3 Cu2 55.66(2) . . ? Cu1 I1 Cu3 60.75(2) . 1_645 ? Cu2 I2 Cu3 67.23(3) . . ? Cu2 I2 Cu2 69.98(3) . 2_566 ? Cu3 I2 Cu2 116.31(3) . 2_566 ? Cu1 I3 Cu2 70.89(2) 1_465 . ? Cu1 I3 Cu3 58.29(2) 1_465 . ? Cu2 I3 Cu3 65.16(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 110.7(5) . . ? N1 C2 C1 125.7(5) . . ? N2 C2 C1 123.7(5) . . ? C4 C3 N1 110.6(5) . . ? C4 C3 H3 124.7 . . ? N1 C3 H3 124.7 . . ? C3 C4 N2 105.8(5) . . ? C3 C4 H4 127.1 . . ? N2 C4 H4 127.1 . . ? N2 C5 C6 111.9(5) . . ? N2 C5 H5A 109.2 . . ? C6 C5 H5A 109.2 . . ? N2 C5 H5B 109.2 . . ? C6 C5 H5B 109.2 . . ? H5A C5 H5B 107.9 . . ? C5 C6 C7 113.2(5) . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? C7 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 114.6(5) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N4 C8 C7 110.9(4) . . ? N4 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? N4 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N4 110.9(4) . . ? N3 C10 C9 124.9(5) . . ? N4 C10 C9 124.1(5) . . ? C12 C11 N4 107.1(5) . . ? C12 C11 H11 126.5 . . ? N4 C11 H11 126.5 . . ? C11 C12 N3 109.6(5) . . ? C11 C12 H12 125.2 . . ? N3 C12 H12 125.2 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C14 N6 110.5(4) . . ? N5 C14 C13 125.9(5) . . ? N6 C14 C13 123.6(4) . . ? C16 C15 N5 110.6(5) . . ? C16 C15 H15 124.7 . . ? N5 C15 H15 124.7 . . ? C15 C16 N6 105.4(4) . . ? C15 C16 H16 127.3 . . ? N6 C16 H16 127.3 . . ? N6 C17 C18 112.1(4) . . ? N6 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N6 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C18 111.9(5) . 2_476 ? C17 C18 H18A 109.2 . . ? C18 C18 H18A 109.2 2_476 . ? C17 C18 H18B 109.2 . . ? C18 C18 H18B 109.2 2_476 . ? H18A C18 H18B 107.9 . . ? C2 N1 C3 105.2(4) . . ? C2 N1 Cu1 130.2(4) . . ? C3 N1 Cu1 124.1(4) . . ? C2 N2 C4 107.7(4) . . ? C2 N2 C5 128.1(5) . . ? C4 N2 C5 124.2(5) . . ? C10 N3 C12 105.5(4) . . ? C10 N3 Cu3 128.5(4) . . ? C12 N3 Cu3 125.8(3) . . ? C10 N4 C11 106.9(4) . . ? C10 N4 C8 127.5(4) . . ? C11 N4 C8 125.6(4) . . ? C14 N5 C15 105.8(4) . . ? C14 N5 Cu2 129.9(3) . . ? C15 N5 Cu2 124.3(3) . . ? C14 N6 C16 107.7(4) . . ? C14 N6 C17 125.3(4) . . ? C16 N6 C17 127.0(4) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.722 _refine_diff_density_min -0.676 _refine_diff_density_rms 0.110 _database_code_depnum_ccdc_archive 'CCDC 921647' ####################################################################### # # 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_p4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 Cu2 I2 N2' _chemical_formula_weight 486.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pmma ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z' 'x+1/2, -y, -z' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z' '-x-1/2, y, z' _cell_length_a 8.3121(14) _cell_length_b 12.843(2) _cell_length_c 10.0096(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1068.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2546 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 27.54 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.021 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 876 _exptl_absorpt_coefficient_mu 9.707 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4436 _exptl_absorpt_correction_T_max 0.5106 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5019 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1028 _reflns_number_gt 917 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0390P)^2^+1.0909P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0018(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1028 _refine_ls_number_parameters 94 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0254 _refine_ls_R_factor_gt 0.0229 _refine_ls_wR_factor_ref 0.0650 _refine_ls_wR_factor_gt 0.0631 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.5000 0.87571(8) 0.5000 0.0486(3) Uani 1 2 d S . . Cu2 Cu 0.2500 0.88025(6) 0.29770(7) 0.0467(2) Uani 1 2 d S . . I1 I 0.51334(4) 1.0000 0.28837(4) 0.03260(17) Uani 1 2 d S . . I2 I 0.2500 0.74959(3) 0.49907(3) 0.03333(18) Uani 1 2 d S . . C1 C 0.3174(10) 0.7113(6) 0.1024(7) 0.0370(17) Uani 0.50 1 d P . . H1 H 0.3619 0.6669 0.1701 0.044 Uiso 0.50 1 d PR . . C2 C 0.2149(15) 0.8435(7) 0.0016(6) 0.045(5) Uani 0.50 1 d P . . H2 H 0.1731 0.9121 -0.0143 0.055 Uiso 0.50 1 d PR . . C3 C 0.2500 0.7718(5) -0.0943(6) 0.0491(17) Uani 1 2 d S . . H3 H 0.2115 0.7771 -0.1845 0.059 Uiso 0.50 1 d PR . . C4 C 0.4908(12) 0.5000 -0.2704(11) 0.026(2) Uani 0.50 2 d SP . . H4 H 0.5391 0.5000 -0.3542 0.032 Uiso 0.50 2 calc SPR . . C5 C 0.4539(11) 0.5943(7) -0.2064(8) 0.0391(18) Uani 0.50 1 d P . . H5 H 0.4877 0.6594 -0.2444 0.047 Uiso 0.50 1 d PR . . C6 C 0.3693(10) 0.5925(6) -0.0894(7) 0.0328(16) Uani 0.50 1 d P . . C7 C 0.3257(14) 0.5000 -0.0323(10) 0.035(2) Uani 0.50 2 d SP . . H7 H 0.2500 0.5000 0.0491 0.042 Uiso 1 4 d SR . . N1 N 0.2500 0.8014(4) 0.1251(4) 0.0360(11) Uani 1 2 d S . . N2 N 0.3186(9) 0.6878(5) -0.0298(6) 0.0362(15) Uani 0.50 1 d P . . 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 0.0444(5) 0.0500(6) 0.0513(5) 0.000 -0.0005(3) 0.000 Cu2 0.0576(5) 0.0461(5) 0.0364(4) -0.0076(3) 0.000 0.000 I1 0.0316(2) 0.0316(3) 0.0346(3) 0.000 0.00203(13) 0.000 I2 0.0299(3) 0.0336(3) 0.0364(3) 0.00229(14) 0.000 0.000 C1 0.052(4) 0.031(4) 0.028(3) 0.004(3) -0.006(3) 0.002(4) C2 0.061(15) 0.037(4) 0.038(4) 0.003(3) -0.003(4) 0.006(4) C3 0.089(5) 0.029(3) 0.030(3) 0.004(3) 0.000 0.000 C4 0.045(7) 0.014(5) 0.020(5) 0.000 0.015(4) 0.000 C5 0.051(5) 0.028(4) 0.037(4) 0.006(3) 0.001(4) -0.007(4) C6 0.044(4) 0.026(4) 0.028(4) 0.000(3) 0.003(3) 0.001(3) C7 0.045(6) 0.035(6) 0.025(5) 0.000 0.007(5) 0.000 N1 0.052(3) 0.029(3) 0.027(2) -0.0009(19) 0.000 0.000 N2 0.056(4) 0.028(3) 0.025(3) 0.000(3) 0.003(3) -0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 I2 2.6348(7) . ? Cu1 I2 2.6348(7) 6_656 ? Cu1 I1 2.6548(7) 5_676 ? Cu1 I1 2.6548(7) . ? Cu1 Cu2 2.9021(6) 6_656 ? Cu1 Cu2 2.9021(6) . ? Cu2 N1 2.002(4) . ? Cu2 I2 2.6228(9) . ? Cu2 I1 2.6768(6) . ? Cu2 I1 2.6768(6) 2_575 ? Cu2 Cu1 2.9021(6) 6_556 ? I1 Cu1 2.6548(7) 5_676 ? I1 Cu2 2.6768(6) 2_575 ? I2 Cu1 2.6348(7) 6_556 ? C1 N1 1.306(9) . ? C1 N2 1.357(9) . ? C1 H1 0.9602 . ? C2 C3 1.362(10) . ? C2 N1 1.381(8) . ? C2 H2 0.9600 . ? C3 C2 1.362(10) 8_655 ? C3 N2 1.380(9) 8_655 ? C3 N2 1.380(9) . ? C3 H3 0.9602 . ? C4 C5 1.404(10) 7_565 ? C4 C5 1.404(10) . ? C4 H4 0.9300 . ? C5 C6 1.366(11) . ? C5 H5 0.9601 . ? C6 C7 1.368(9) . ? C6 N2 1.425(10) . ? C7 C6 1.368(9) 7_565 ? C7 H7 1.0290 . ? N1 C1 1.306(9) 8_655 ? N1 C2 1.381(8) 8_655 ? N2 N2 1.140(15) 8_655 ? N2 C1 1.765(10) 8_655 ? 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 I2 Cu1 I2 104.13(4) . 6_656 ? I2 Cu1 I1 109.850(11) . 5_676 ? I2 Cu1 I1 113.564(11) 6_656 5_676 ? I2 Cu1 I1 113.564(11) . . ? I2 Cu1 I1 109.850(11) 6_656 . ? I1 Cu1 I1 106.07(4) 5_676 . ? I2 Cu1 Cu2 125.42(3) . 6_656 ? I2 Cu1 Cu2 56.300(18) 6_656 6_656 ? I1 Cu1 Cu2 57.388(19) 5_676 6_656 ? I1 Cu1 Cu2 120.98(3) . 6_656 ? I2 Cu1 Cu2 56.299(18) . . ? I2 Cu1 Cu2 125.42(3) 6_656 . ? I1 Cu1 Cu2 120.98(3) 5_676 . ? I1 Cu1 Cu2 57.388(19) . . ? Cu2 Cu1 Cu2 177.70(5) 6_656 . ? N1 Cu2 I2 109.84(14) . . ? N1 Cu2 I1 105.10(7) . . ? I2 Cu2 I1 113.230(19) . . ? N1 Cu2 I1 105.10(7) . 2_575 ? I2 Cu2 I1 113.230(19) . 2_575 ? I1 Cu2 I1 109.71(3) . 2_575 ? N1 Cu2 Cu1 126.29(7) . . ? I2 Cu2 Cu1 56.69(2) . . ? I1 Cu2 Cu1 56.658(19) . . ? I1 Cu2 Cu1 128.42(3) 2_575 . ? N1 Cu2 Cu1 126.29(7) . 6_556 ? I2 Cu2 Cu1 56.69(2) . 6_556 ? I1 Cu2 Cu1 128.42(3) . 6_556 ? I1 Cu2 Cu1 56.658(19) 2_575 6_556 ? Cu1 Cu2 Cu1 91.46(2) . 6_556 ? Cu1 I1 Cu1 73.93(4) 5_676 . ? Cu1 I1 Cu2 106.47(2) 5_676 . ? Cu1 I1 Cu2 65.955(18) . . ? Cu1 I1 Cu2 65.955(18) 5_676 2_575 ? Cu1 I1 Cu2 106.47(2) . 2_575 ? Cu2 I1 Cu2 70.14(3) . 2_575 ? Cu2 I2 Cu1 67.006(15) . . ? Cu2 I2 Cu1 67.006(15) . 6_556 ? Cu1 I2 Cu1 104.13(4) . 6_556 ? C1 C1 N1 64.6(4) 8_655 . ? C1 C1 N2 90.4(4) 8_655 . ? N1 C1 N2 111.7(6) . . ? C1 C1 N2 50.2(3) 8_655 8_655 ? N1 C1 N2 90.4(5) . 8_655 ? C1 C1 C2 82.3(4) 8_655 8_655 ? N2 C1 C2 72.4(4) . 8_655 ? N2 C1 C2 71.3(4) 8_655 8_655 ? C1 C1 H1 112.7 8_655 . ? N1 C1 H1 124.6 . . ? N2 C1 H1 123.7 . . ? N2 C1 H1 132.4 8_655 . ? C2 C1 H1 156.2 8_655 . ? C2 C2 C3 77.6(5) 8_655 . ? C2 C2 N1 77.8(5) 8_655 . ? C3 C2 N1 108.7(7) . . ? C2 C2 C1 97.7(4) 8_655 8_655 ? C3 C2 C1 79.0(6) . 8_655 ? C2 C2 H2 111.2 8_655 . ? C3 C2 H2 125.6 . . ? N1 C2 H2 125.7 . . ? C1 C2 H2 144.7 8_655 . ? C2 C3 N2 106.7(6) 8_655 8_655 ? C2 C3 N2 96.4(6) . 8_655 ? C2 C3 N2 96.4(6) 8_655 . ? C2 C3 N2 106.7(6) . . ? C2 C3 H3 133.3 8_655 . ? C2 C3 H3 122.9 . . ? N2 C3 H3 111.0 8_655 . ? N2 C3 H3 129.3 . . ? C5 C4 C5 119.2(10) 7_565 . ? C5 C4 H4 120.4 7_565 . ? C5 C4 H4 120.4 . . ? C6 C5 C4 119.3(8) . . ? C6 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C5 C6 C7 120.6(8) . . ? C5 C6 N2 119.8(7) . . ? C7 C6 N2 119.5(7) . . ? C5 C6 C6 121.0(5) . 8_655 ? C7 C6 C6 74.6(6) . 8_655 ? N2 C6 C6 72.8(4) . 8_655 ? C7 C7 C6 105.4(6) 2_565 . ? C7 C7 C6 105.4(6) 2_565 7_565 ? C6 C7 C6 120.7(10) . 7_565 ? C6 C7 H7 119.5 . . ? C6 C7 H7 119.5 7_565 . ? C1 N1 C2 95.8(6) 8_655 . ? C1 N1 C2 106.3(6) . . ? C1 N1 C2 106.3(6) 8_655 8_655 ? C1 N1 C2 95.8(6) . 8_655 ? C1 N1 Cu2 126.8(4) 8_655 . ? C1 N1 Cu2 126.8(4) . . ? C2 N1 Cu2 125.1(5) . . ? C2 N1 Cu2 125.1(5) 8_655 . ? N2 N2 C1 89.6(4) 8_655 . ? N2 N2 C3 65.6(3) 8_655 . ? C1 N2 C3 106.2(6) . . ? N2 N2 C6 107.2(4) 8_655 . ? C1 N2 C6 127.0(6) . . ? C3 N2 C6 126.6(6) . . ? N2 N2 C1 50.2(3) 8_655 8_655 ? C3 N2 C1 87.3(5) . 8_655 ? C6 N2 C1 130.5(6) . 8_655 ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 1.316 _refine_diff_density_min -0.767 _refine_diff_density_rms 0.123 _database_code_depnum_ccdc_archive 'CCDC 921648' ####################################################################### # # 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_p5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cu I N4' _chemical_formula_weight 400.68 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M p-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7974(16) _cell_length_b 9.6942(19) _cell_length_c 11.209(2) _cell_angle_alpha 115.680(3) _cell_angle_beta 101.089(3) _cell_angle_gamma 109.236(3) _cell_volume 662.7(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 3.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6927 _exptl_absorpt_correction_T_max 0.8265 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3314 _diffrn_reflns_av_R_equivalents 0.0184 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2309 _reflns_number_gt 1975 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+0.7605P] 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 2309 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0310 _refine_ls_wR_factor_ref 0.0790 _refine_ls_wR_factor_gt 0.0742 _refine_ls_goodness_of_fit_ref 1.009 _refine_ls_restrained_S_all 1.009 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu -0.08488(9) 0.50522(7) -0.16264(6) 0.05658(18) Uani 1 1 d . . . I1 I -0.42503(4) 0.50218(4) -0.20892(4) 0.06204(15) Uani 1 1 d . . . C1 C 0.3206(6) 0.7774(5) 0.0371(5) 0.0466(10) Uani 1 1 d . . . H1 H 0.3706 0.6987 0.0162 0.056 Uiso 1 1 calc R . . C2 C 0.1231(7) 0.8873(6) 0.0392(5) 0.0533(11) Uani 1 1 d . . . H2 H 0.0076 0.8967 0.0189 0.064 Uiso 1 1 calc R . . C3 C 0.3033(7) 1.0204(6) 0.1302(5) 0.0542(11) Uani 1 1 d . . . H3 H 0.3354 1.1368 0.1829 0.065 Uiso 1 1 calc R . . C4 C 0.6403(6) 1.0406(5) 0.2133(4) 0.0420(9) Uani 1 1 d . . . C5 C 0.7466(7) 1.2169(5) 0.2714(5) 0.0518(11) Uani 1 1 d . . . H5 H 0.6834 1.2790 0.2592 0.062 Uiso 1 1 calc R . . C6 C 0.9470(7) 1.2976(6) 0.3474(5) 0.0589(12) Uani 1 1 d . . . H6 H 1.0193 1.4158 0.3869 0.071 Uiso 1 1 calc R . . C7 C 1.0446(7) 1.2083(6) 0.3669(5) 0.0556(11) Uani 1 1 d . . . H7 H 1.1808 1.2646 0.4170 0.067 Uiso 1 1 calc R . . C8 C 0.9350(6) 1.0333(5) 0.3103(4) 0.0422(9) Uani 1 1 d . . . C9 C 0.7334(6) 0.9491(5) 0.2339(4) 0.0421(9) Uani 1 1 d . . . H9 H 0.6607 0.8315 0.1965 0.051 Uiso 1 1 calc R . . C10 C 0.9659(6) 0.7661(5) 0.2369(5) 0.0476(10) Uani 1 1 d . . . H10 H 0.8478 0.6930 0.1560 0.057 Uiso 1 1 calc R . . C11 C 1.2443(6) 0.8633(6) 0.4002(5) 0.0573(12) Uani 1 1 d . . . H11 H 1.3555 0.8678 0.4535 0.069 Uiso 1 1 calc R . . C12 C 1.2084(6) 0.9975(6) 0.4320(5) 0.0538(11) Uani 1 1 d . . . H12 H 1.2890 1.1108 0.5095 0.065 Uiso 1 1 calc R . . N1 N 0.1340(5) 0.7344(5) -0.0199(4) 0.0485(8) Uani 1 1 d . . . N2 N 0.4323(5) 0.9509(4) 0.1304(4) 0.0417(8) Uani 1 1 d . . . N3 N 1.0290(5) 0.9361(4) 0.3281(3) 0.0433(8) Uani 1 1 d . . . N4 N 1.0915(5) 0.7165(5) 0.2762(4) 0.0493(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0541(3) 0.0512(3) 0.0625(4) 0.0281(3) 0.0183(3) 0.0284(3) I1 0.04311(19) 0.0472(2) 0.0922(3) 0.03501(18) 0.01994(16) 0.02425(14) C1 0.048(2) 0.044(2) 0.055(3) 0.026(2) 0.018(2) 0.030(2) C2 0.054(3) 0.055(3) 0.073(3) 0.040(3) 0.028(2) 0.039(2) C3 0.062(3) 0.047(3) 0.072(3) 0.034(2) 0.032(3) 0.040(2) C4 0.050(2) 0.036(2) 0.042(2) 0.0192(18) 0.0221(19) 0.0231(19) C5 0.064(3) 0.038(2) 0.060(3) 0.025(2) 0.030(2) 0.029(2) C6 0.066(3) 0.034(2) 0.066(3) 0.021(2) 0.028(3) 0.018(2) C7 0.047(3) 0.040(2) 0.057(3) 0.016(2) 0.018(2) 0.012(2) C8 0.044(2) 0.039(2) 0.041(2) 0.0180(18) 0.0190(18) 0.0194(18) C9 0.045(2) 0.032(2) 0.043(2) 0.0163(18) 0.0160(18) 0.0174(18) C10 0.037(2) 0.045(2) 0.047(2) 0.016(2) 0.0115(19) 0.0197(19) C11 0.039(2) 0.063(3) 0.056(3) 0.025(2) 0.008(2) 0.025(2) C12 0.041(2) 0.051(3) 0.042(2) 0.012(2) 0.0056(19) 0.016(2) N1 0.047(2) 0.048(2) 0.055(2) 0.0278(18) 0.0172(17) 0.0293(17) N2 0.0453(19) 0.0378(18) 0.0455(19) 0.0218(16) 0.0177(16) 0.0240(15) N3 0.0356(18) 0.0407(19) 0.0425(19) 0.0160(16) 0.0119(15) 0.0167(15) N4 0.0344(18) 0.050(2) 0.053(2) 0.0210(18) 0.0098(16) 0.0210(16) _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 N4 1.943(4) 2_665 ? Cu1 N1 1.944(4) . ? Cu1 I1 2.5904(8) . ? C1 N1 1.308(5) . ? C1 N2 1.357(5) . ? C1 H1 0.9300 . ? C2 C3 1.339(7) . ? C2 N1 1.377(5) . ? C2 H2 0.9300 . ? C3 N2 1.382(5) . ? C3 H3 0.9300 . ? C4 C9 1.380(6) . ? C4 C5 1.388(6) . ? C4 N2 1.429(5) . ? C5 C6 1.373(7) . ? C5 H5 0.9300 . ? C6 C7 1.382(7) . ? C6 H6 0.9300 . ? C7 C8 1.384(6) . ? C7 H7 0.9300 . ? C8 C9 1.379(6) . ? C8 N3 1.425(5) . ? C9 H9 0.9300 . ? C10 N4 1.308(5) . ? C10 N3 1.347(5) . ? C10 H10 0.9300 . ? C11 C12 1.332(7) . ? C11 N4 1.381(6) . ? C11 H11 0.9300 . ? C12 N3 1.375(5) . ? C12 H12 0.9300 . ? N4 Cu1 1.943(4) 2_665 ? 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 N4 Cu1 N1 131.54(14) 2_665 . ? N4 Cu1 I1 115.57(10) 2_665 . ? N1 Cu1 I1 112.88(10) . . ? N1 C1 N2 111.7(4) . . ? N1 C1 H1 124.2 . . ? N2 C1 H1 124.2 . . ? C3 C2 N1 110.0(4) . . ? C3 C2 H2 125.0 . . ? N1 C2 H2 125.0 . . ? C2 C3 N2 106.6(4) . . ? C2 C3 H3 126.7 . . ? N2 C3 H3 126.7 . . ? C9 C4 C5 120.8(4) . . ? C9 C4 N2 119.0(4) . . ? C5 C4 N2 120.3(4) . . ? C6 C5 C4 118.5(4) . . ? C6 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? C5 C6 C7 121.9(4) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C6 C7 C8 118.5(4) . . ? C6 C7 H7 120.7 . . ? C8 C7 H7 120.7 . . ? C9 C8 C7 120.8(4) . . ? C9 C8 N3 118.7(4) . . ? C7 C8 N3 120.5(4) . . ? C8 C9 C4 119.5(4) . . ? C8 C9 H9 120.3 . . ? C4 C9 H9 120.3 . . ? N4 C10 N3 111.6(4) . . ? N4 C10 H10 124.2 . . ? N3 C10 H10 124.2 . . ? C12 C11 N4 109.8(4) . . ? C12 C11 H11 125.1 . . ? N4 C11 H11 125.1 . . ? C11 C12 N3 106.7(4) . . ? C11 C12 H12 126.6 . . ? N3 C12 H12 126.6 . . ? C1 N1 C2 105.7(4) . . ? C1 N1 Cu1 128.1(3) . . ? C2 N1 Cu1 126.1(3) . . ? C1 N2 C3 106.0(4) . . ? C1 N2 C4 126.2(3) . . ? C3 N2 C4 127.8(4) . . ? C10 N3 C12 106.4(4) . . ? C10 N3 C8 125.8(3) . . ? C12 N3 C8 127.5(4) . . ? C10 N4 C11 105.4(4) . . ? C10 N4 Cu1 126.1(3) . 2_665 ? C11 N4 Cu1 127.6(3) . 2_665 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.023 _refine_diff_density_min -0.830 _refine_diff_density_rms 0.081 _database_code_depnum_ccdc_archive 'CCDC 921649' ####################################################################### # # 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_p6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cu4 I4 N4' _chemical_formula_weight 972.00 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M c2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 43.528(14) _cell_length_b 4.1804(13) _cell_length_c 24.057(7) _cell_angle_alpha 90.00 _cell_angle_beta 115.413(5) _cell_angle_gamma 90.00 _cell_volume 3954(2) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3504 _exptl_absorpt_coefficient_mu 10.494 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3021 _exptl_absorpt_correction_T_max 0.4873 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9159 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -49 _diffrn_reflns_limit_h_max 50 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3435 _reflns_number_gt 2491 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+5.5977P] 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 3435 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0898 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.65071(4) 0.9569(3) 0.30506(6) 0.0599(4) Uani 1 1 d . . . Cu2 Cu 0.46293(3) 0.0760(3) 0.31256(6) 0.0545(4) Uani 1 1 d . . . Cu3 Cu 0.54340(3) 0.5360(3) 0.27175(6) 0.0501(4) Uani 1 1 d . . . Cu4 Cu 0.70032(3) 1.4030(3) 0.36224(6) 0.0474(3) Uani 1 1 d . . . I1 I 0.508631(15) 0.55972(14) 0.34103(3) 0.03190(17) Uani 1 1 d . . . I2 I 0.653992(16) 1.45354(13) 0.24150(3) 0.03318(17) Uani 1 1 d . . . I3 I 0.584361(15) 1.02853(13) 0.30027(3) 0.03374(17) Uani 1 1 d . . . I4 I 0.691333(18) 0.90408(14) 0.42104(3) 0.04093(19) Uani 1 1 d . . . C1 C 0.4213(2) -0.046(2) 0.3817(4) 0.035(2) Uani 1 1 d . . . H1 H 0.4041 -0.1432 0.3478 0.042 Uiso 1 1 calc R . . C2 C 0.4672(3) 0.195(3) 0.4402(4) 0.047(3) Uani 1 1 d . . . H2 H 0.4881 0.2981 0.4537 0.057 Uiso 1 1 calc R . . C3 C 0.4510(2) 0.135(3) 0.4751(4) 0.047(3) Uani 1 1 d . . . H3 H 0.4582 0.1887 0.5163 0.057 Uiso 1 1 calc R . . C4 C 0.3953(2) -0.133(2) 0.4545(4) 0.033(2) Uani 1 1 d . . . C5 C 0.4049(3) -0.288(2) 0.5107(4) 0.044(3) Uani 1 1 d . . . H5 H 0.4277 -0.3130 0.5373 0.053 Uiso 1 1 calc R . . C6 C 0.3801(3) -0.403(2) 0.5265(4) 0.049(3) Uani 1 1 d . . . H6 H 0.3864 -0.5049 0.5642 0.059 Uiso 1 1 calc R . . C7 C 0.3455(3) -0.370(2) 0.4864(4) 0.047(3) Uani 1 1 d . . . H7 H 0.3289 -0.4557 0.4966 0.056 Uiso 1 1 calc R . . C8 C 0.3364(2) -0.206(2) 0.4312(4) 0.029(2) Uani 1 1 d . . . C9 C 0.3612(2) -0.0913(19) 0.4152(4) 0.031(2) Uani 1 1 d . . . H9 H 0.3551 0.0145 0.3779 0.038 Uiso 1 1 calc R . . C10 C 0.2746(3) -0.196(2) 0.4040(4) 0.045(3) Uani 1 1 d . . . H10 H 0.2761 -0.2944 0.4398 0.054 Uiso 1 1 calc R . . C11 C 0.2889(3) -0.002(3) 0.3354(5) 0.057(3) Uani 1 1 d . . . H11 H 0.3009 0.0626 0.3134 0.068 Uiso 1 1 calc R . . C12 C 0.2550(3) 0.024(2) 0.3178(4) 0.049(3) Uani 1 1 d . . . H12 H 0.2397 0.1157 0.2810 0.059 Uiso 1 1 calc R . . N1 N 0.4484(2) 0.0836(18) 0.3807(3) 0.0367(19) Uani 1 1 d . . . N2 N 0.42105(18) -0.0237(17) 0.4377(3) 0.0348(18) Uani 1 1 d . . . N3 N 0.30188(19) -0.1442(17) 0.3930(3) 0.0346(18) Uani 1 1 d . . . N4 N 0.24614(19) -0.1019(18) 0.3615(3) 0.0384(19) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0883(12) 0.0382(8) 0.0465(8) -0.0021(6) 0.0225(8) -0.0091(7) Cu2 0.0506(9) 0.0751(10) 0.0420(8) -0.0002(6) 0.0238(7) -0.0116(7) Cu3 0.0464(8) 0.0447(8) 0.0571(8) -0.0058(6) 0.0203(7) -0.0030(6) Cu4 0.0422(8) 0.0518(8) 0.0565(8) -0.0017(6) 0.0293(7) -0.0042(6) I1 0.0304(3) 0.0310(3) 0.0334(3) -0.0003(2) 0.0128(3) -0.0003(3) I2 0.0406(4) 0.0256(3) 0.0323(3) 0.0007(2) 0.0147(3) 0.0013(3) I3 0.0287(3) 0.0288(3) 0.0413(4) 0.0002(3) 0.0127(3) -0.0005(2) I4 0.0634(5) 0.0291(4) 0.0342(4) 0.0008(3) 0.0246(3) 0.0000(3) C1 0.027(5) 0.040(6) 0.037(5) 0.000(4) 0.011(4) 0.009(4) C2 0.034(6) 0.070(7) 0.034(6) -0.019(5) 0.010(5) -0.014(5) C3 0.023(5) 0.089(8) 0.029(5) -0.021(5) 0.009(4) -0.012(5) C4 0.026(5) 0.051(6) 0.028(5) 0.005(4) 0.016(4) 0.004(4) C5 0.038(6) 0.063(7) 0.035(6) 0.002(5) 0.020(5) 0.013(5) C6 0.054(7) 0.068(8) 0.033(6) 0.011(5) 0.026(5) 0.022(6) C7 0.048(7) 0.059(7) 0.041(6) 0.014(5) 0.027(5) 0.003(5) C8 0.038(6) 0.028(5) 0.029(5) 0.004(4) 0.023(4) 0.002(4) C9 0.032(5) 0.031(5) 0.025(5) 0.004(4) 0.006(4) 0.007(4) C10 0.041(7) 0.060(7) 0.040(6) 0.005(5) 0.024(5) 0.003(5) C11 0.033(6) 0.090(9) 0.049(7) 0.029(6) 0.020(5) 0.008(6) C12 0.043(7) 0.073(8) 0.038(6) 0.017(5) 0.023(5) -0.003(6) N1 0.035(5) 0.047(5) 0.031(4) 0.003(3) 0.016(4) 0.000(4) N2 0.025(4) 0.050(5) 0.031(4) -0.005(3) 0.014(4) 0.000(4) N3 0.026(4) 0.042(5) 0.037(5) 0.003(4) 0.014(4) 0.002(4) N4 0.031(5) 0.043(5) 0.046(5) 0.001(4) 0.021(4) -0.002(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 I4 2.5935(16) . ? Cu1 I2 2.6183(15) . ? Cu1 I2 2.6408(15) 1_545 ? Cu1 Cu4 2.7358(19) . ? Cu1 I3 2.856(2) . ? Cu2 N1 1.994(7) . ? Cu2 I3 2.6170(15) 2_645 ? Cu2 I1 2.7103(16) . ? Cu2 Cu3 2.7218(19) 2_655 ? Cu2 I1 2.8134(17) 1_545 ? Cu2 Cu3 2.968(2) 2_645 ? Cu3 I3 2.6150(15) . ? Cu3 I3 2.6646(15) 1_545 ? Cu3 I1 2.6882(15) 2_655 ? Cu3 I1 2.6913(16) . ? Cu3 Cu2 2.7218(19) 2_655 ? Cu3 Cu2 2.968(2) 2_665 ? Cu4 N4 2.002(8) 3_565 ? Cu4 I4 2.6420(15) . ? Cu4 I4 2.6488(15) 1_565 ? Cu4 I2 2.7423(15) . ? I1 Cu3 2.6882(15) 2_655 ? I1 Cu2 2.8134(17) 1_565 ? I2 Cu1 2.6408(15) 1_565 ? I3 Cu2 2.6170(15) 2_665 ? I3 Cu3 2.6646(15) 1_565 ? I4 Cu4 2.6488(15) 1_545 ? C1 N1 1.310(11) . ? C1 N2 1.352(11) . ? C2 C3 1.331(13) . ? C2 N1 1.389(11) . ? C3 N2 1.394(11) . ? C4 C9 1.385(12) . ? C4 C5 1.392(12) . ? C4 N2 1.423(11) . ? C5 C6 1.374(13) . ? C6 C7 1.404(14) . ? C7 C8 1.390(11) . ? C8 C9 1.382(12) . ? C8 N3 1.407(11) . ? C10 N4 1.283(11) . ? C10 N3 1.341(11) . ? C11 C12 1.353(14) . ? C11 N3 1.387(11) . ? C12 N4 1.372(11) . ? N4 Cu4 2.002(8) 3_435 ? 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 I4 Cu1 I2 120.86(6) . . ? I4 Cu1 I2 111.94(6) . 1_545 ? I2 Cu1 I2 105.29(6) . 1_545 ? I4 Cu1 Cu4 59.37(4) . . ? I2 Cu1 Cu4 61.57(4) . . ? I2 Cu1 Cu4 127.38(7) 1_545 . ? I4 Cu1 I3 105.26(5) . . ? I2 Cu1 I3 101.60(5) . . ? I2 Cu1 I3 111.42(5) 1_545 . ? Cu4 Cu1 I3 121.01(6) . . ? N1 Cu2 I3 117.9(2) . 2_645 ? N1 Cu2 I1 103.7(2) . . ? I3 Cu2 I1 118.94(5) 2_645 . ? N1 Cu2 Cu3 129.4(2) . 2_655 ? I3 Cu2 Cu3 59.84(4) 2_645 2_655 ? I1 Cu2 Cu3 59.32(4) . 2_655 ? N1 Cu2 I1 104.6(2) . 1_545 ? I3 Cu2 I1 110.70(5) 2_645 1_545 ? I1 Cu2 I1 98.35(5) . 1_545 ? Cu3 Cu2 I1 123.94(6) 2_655 1_545 ? N1 Cu2 Cu3 127.2(2) . 2_645 ? I3 Cu2 Cu3 55.41(4) 2_645 2_645 ? I1 Cu2 Cu3 125.66(6) . 2_645 ? Cu3 Cu2 Cu3 94.48(6) 2_655 2_645 ? I1 Cu2 Cu3 55.34(4) 1_545 2_645 ? I3 Cu3 I3 104.71(6) . 1_545 ? I3 Cu3 I1 114.84(5) . 2_655 ? I3 Cu3 I1 118.04(5) 1_545 2_655 ? I3 Cu3 I1 108.05(5) . . ? I3 Cu3 I1 111.21(5) 1_545 . ? I1 Cu3 I1 99.76(5) 2_655 . ? I3 Cu3 Cu2 126.25(6) . 2_655 ? I3 Cu3 Cu2 58.13(4) 1_545 2_655 ? I1 Cu3 Cu2 60.13(4) 2_655 2_655 ? I1 Cu3 Cu2 125.70(6) . 2_655 ? I3 Cu3 Cu2 55.48(4) . 2_665 ? I3 Cu3 Cu2 129.59(6) 1_545 2_665 ? I1 Cu3 Cu2 59.42(4) 2_655 2_665 ? I1 Cu3 Cu2 118.90(5) . 2_665 ? Cu2 Cu3 Cu2 94.48(6) 2_655 2_665 ? N4 Cu4 I4 111.9(2) 3_565 . ? N4 Cu4 I4 112.9(2) 3_565 1_565 ? I4 Cu4 I4 104.40(5) . 1_565 ? N4 Cu4 Cu1 124.3(2) 3_565 . ? I4 Cu4 Cu1 57.64(4) . . ? I4 Cu4 Cu1 122.82(6) 1_565 . ? N4 Cu4 I2 105.9(2) 3_565 . ? I4 Cu4 I2 114.67(5) . . ? I4 Cu4 I2 107.14(5) 1_565 . ? Cu1 Cu4 I2 57.11(4) . . ? Cu3 I1 Cu3 80.09(5) 2_655 . ? Cu3 I1 Cu2 60.55(4) 2_655 . ? Cu3 I1 Cu2 111.28(5) . . ? Cu3 I1 Cu2 65.24(4) 2_655 1_565 ? Cu3 I1 Cu2 113.85(4) . 1_565 ? Cu2 I1 Cu2 98.35(5) . 1_565 ? Cu1 I2 Cu1 105.29(6) . 1_565 ? Cu1 I2 Cu4 61.32(4) . . ? Cu1 I2 Cu4 69.27(4) 1_565 . ? Cu3 I3 Cu2 69.11(5) . 2_665 ? Cu3 I3 Cu3 104.71(6) . 1_565 ? Cu2 I3 Cu3 62.03(4) 2_665 1_565 ? Cu3 I3 Cu1 119.46(5) . . ? Cu2 I3 Cu1 112.42(5) 2_665 . ? Cu3 I3 Cu1 130.32(5) 1_565 . ? Cu1 I4 Cu4 63.00(4) . . ? Cu1 I4 Cu4 71.43(5) . 1_545 ? Cu4 I4 Cu4 104.40(5) . 1_545 ? N1 C1 N2 112.4(8) . . ? C3 C2 N1 110.5(9) . . ? C2 C3 N2 106.5(8) . . ? C9 C4 C5 120.6(9) . . ? C9 C4 N2 120.5(8) . . ? C5 C4 N2 118.8(8) . . ? C6 C5 C4 119.2(9) . . ? C5 C6 C7 120.7(9) . . ? C8 C7 C6 119.3(9) . . ? C9 C8 C7 119.9(8) . . ? C9 C8 N3 119.8(7) . . ? C7 C8 N3 120.2(8) . . ? C8 C9 C4 120.1(8) . . ? N4 C10 N3 115.3(9) . . ? C12 C11 N3 105.7(9) . . ? C11 C12 N4 110.8(9) . . ? C1 N1 C2 104.9(8) . . ? C1 N1 Cu2 128.0(6) . . ? C2 N1 Cu2 126.8(6) . . ? C1 N2 C3 105.8(8) . . ? C1 N2 C4 127.2(8) . . ? C3 N2 C4 127.0(8) . . ? C10 N3 C11 104.5(8) . . ? C10 N3 C8 128.9(8) . . ? C11 N3 C8 126.5(8) . . ? C10 N4 C12 103.7(8) . . ? C10 N4 Cu4 128.4(7) . 3_435 ? C12 N4 Cu4 127.7(7) . 3_435 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.625 _refine_diff_density_min -1.462 _refine_diff_density_rms 0.189 _database_code_depnum_ccdc_archive 'CCDC 921650' ####################################################################### # # 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_3-100K _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H27 Cu3 I3 N6' _chemical_formula_sum 'C18 H27 Cu3 I3 N6' _chemical_formula_weight 898.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2669(12) _cell_length_b 10.7531(14) _cell_length_c 11.8781(15) _cell_angle_alpha 106.838(2) _cell_angle_beta 90.109(2) _cell_angle_gamma 101.790(2) _cell_volume 1226.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4005 _cell_measurement_theta_min 4.548 _cell_measurement_theta_max 54.981 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 846 _exptl_absorpt_coefficient_mu 6.374 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4482 _exptl_absorpt_correction_T_max 0.5682 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6135 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -12 _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 14 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4276 _reflns_number_gt 3886 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0438P)^2^+0.1968P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4276 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0293 _refine_ls_R_factor_gt 0.0252 _refine_ls_wR_factor_ref 0.0804 _refine_ls_wR_factor_gt 0.0688 _refine_ls_goodness_of_fit_ref 1.154 _refine_ls_restrained_S_all 1.154 _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 0.70566(6) -0.59825(6) 0.20512(6) 0.01649(16) Uani 1 1 d . . . Cu2 Cu -0.08205(6) 0.51179(6) 0.39695(6) 0.01830(16) Uani 1 1 d . . . Cu3 Cu -0.16520(6) 0.24332(6) 0.26328(6) 0.01675(16) Uani 1 1 d . . . I1 I 0.57536(3) -0.83335(3) 0.18675(3) 0.01803(11) Uani 1 1 d . . . I2 I -0.15161(3) 0.32088(3) 0.49799(3) 0.01481(10) Uani 1 1 d . . . I3 I -0.03830(3) 0.43905(3) 0.16775(3) 0.01395(10) Uani 1 1 d . . . C1 C 0.3829(5) -0.5356(6) 0.2242(5) 0.0197(12) Uani 1 1 d . . . H1A H 0.3171 -0.5934 0.1610 0.030 Uiso 1 1 calc R . . H1B H 0.3391 -0.4754 0.2824 0.030 Uiso 1 1 calc R . . H1C H 0.4217 -0.5903 0.2624 0.030 Uiso 1 1 calc R . . C2 C 0.4899(5) -0.4565(5) 0.1736(5) 0.0149(11) Uani 1 1 d . . . C3 C 0.6780(5) -0.3754(5) 0.1119(5) 0.0158(11) Uani 1 1 d . . . H3 H 0.7695 -0.3603 0.0959 0.019 Uiso 1 1 calc R . . C4 C 0.5891(5) -0.3117(5) 0.0833(5) 0.0181(12) Uani 1 1 d . . . H4 H 0.6055 -0.2443 0.0449 0.022 Uiso 1 1 calc R . . C5 C 0.3420(5) -0.3240(5) 0.1116(5) 0.0168(11) Uani 1 1 d . . . H5A H 0.2668 -0.3996 0.1079 0.020 Uiso 1 1 calc R . . H5B H 0.3364 -0.2993 0.0380 0.020 Uiso 1 1 calc R . . C6 C 0.3304(5) -0.2052(5) 0.2175(5) 0.0176(11) Uani 1 1 d . . . H6A H 0.3421 -0.2286 0.2910 0.021 Uiso 1 1 calc R . . H6B H 0.4033 -0.1287 0.2183 0.021 Uiso 1 1 calc R . . C7 C 0.1980(5) -0.1639(5) 0.2156(5) 0.0188(12) Uani 1 1 d . . . H7A H 0.1878 -0.1039 0.2944 0.023 Uiso 1 1 calc R . . H7B H 0.1252 -0.2440 0.2004 0.023 Uiso 1 1 calc R . . C8 C 0.1832(5) -0.0939(5) 0.1237(5) 0.0171(11) Uani 1 1 d . . . H8A H 0.2605 -0.0188 0.1334 0.020 Uiso 1 1 calc R . . H8B H 0.1830 -0.1568 0.0441 0.020 Uiso 1 1 calc R . . C9 C 0.1487(5) 0.1773(5) 0.2814(5) 0.0233(13) Uani 1 1 d . . . H9A H 0.2134 0.2146 0.2330 0.035 Uiso 1 1 calc R . . H9B H 0.1935 0.1373 0.3304 0.035 Uiso 1 1 calc R . . H9C H 0.1100 0.2482 0.3322 0.035 Uiso 1 1 calc R . . C10 C 0.0418(5) 0.0746(5) 0.2042(4) 0.0134(11) Uani 1 1 d . . . C11 C -0.0607(5) -0.1123(5) 0.0719(5) 0.0153(11) Uani 1 1 d . . . H11 H -0.0787 -0.1981 0.0159 0.018 Uiso 1 1 calc R . . C12 C -0.1481(5) -0.0305(5) 0.1089(4) 0.0167(11) Uani 1 1 d . . . H12 H -0.2394 -0.0506 0.0820 0.020 Uiso 1 1 calc R . . C13 C -0.1111(5) 0.8161(5) 0.3590(5) 0.0184(11) Uani 1 1 d . . . H13A H -0.1492 0.8451 0.2978 0.028 Uiso 1 1 calc R . . H13B H -0.0483 0.7602 0.3245 0.028 Uiso 1 1 calc R . . H13C H -0.0640 0.8941 0.4215 0.028 Uiso 1 1 calc R . . C14 C -0.2194(5) 0.7386(5) 0.4092(4) 0.0158(11) Uani 1 1 d . . . C15 C -0.3386(5) 0.5904(5) 0.4789(5) 0.0164(11) Uani 1 1 d . . . H15 H -0.3661 0.5122 0.5022 0.020 Uiso 1 1 calc R . . C16 C -0.4091(5) 0.6850(5) 0.4899(5) 0.0173(11) Uani 1 1 d . . . H16 H -0.4941 0.6862 0.5212 0.021 Uiso 1 1 calc R . . C17 C -0.3668(5) 0.9037(5) 0.4337(5) 0.0193(12) Uani 1 1 d . . . H17A H -0.3904 0.8916 0.3498 0.023 Uiso 1 1 calc R . . H17B H -0.2887 0.9788 0.4600 0.023 Uiso 1 1 calc R . . C18 C -0.4832(5) 0.9363(5) 0.5064(5) 0.0183(12) Uani 1 1 d . . . H18A H -0.5618 0.8619 0.4796 0.022 Uiso 1 1 calc R . . H18B H -0.4601 0.9479 0.5904 0.022 Uiso 1 1 calc R . . N1 N 0.6169(4) -0.4665(4) 0.1685(4) 0.0144(9) Uani 1 1 d . . . N2 N 0.4686(4) -0.3649(4) 0.1212(4) 0.0144(9) Uani 1 1 d . . . N3 N -0.0829(4) 0.0866(4) 0.1918(4) 0.0144(9) Uani 1 1 d . . . N4 N 0.0598(4) -0.0435(4) 0.1333(4) 0.0136(9) Uani 1 1 d . . . N5 N -0.2202(4) 0.6234(4) 0.4288(4) 0.0148(9) Uani 1 1 d . . . N6 N -0.3318(4) 0.7817(4) 0.4457(4) 0.0142(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0152(3) 0.0174(3) 0.0196(4) 0.0074(3) 0.0028(3) 0.0066(3) Cu2 0.0166(3) 0.0172(3) 0.0234(4) 0.0070(3) 0.0073(3) 0.0073(3) Cu3 0.0174(3) 0.0147(3) 0.0184(3) 0.0024(3) 0.0020(3) 0.0077(3) I1 0.01339(18) 0.0176(2) 0.0235(2) 0.00723(15) 0.00230(14) 0.00255(14) I2 0.01462(18) 0.01568(19) 0.01398(18) 0.00494(14) 0.00207(13) 0.00213(13) I3 0.01331(18) 0.01275(18) 0.01497(19) 0.00267(14) 0.00359(13) 0.00303(13) C1 0.017(3) 0.025(3) 0.020(3) 0.009(2) 0.006(2) 0.007(2) C2 0.019(3) 0.011(3) 0.014(3) 0.001(2) 0.002(2) 0.005(2) C3 0.010(2) 0.018(3) 0.018(3) 0.005(2) 0.001(2) -0.001(2) C4 0.020(3) 0.012(3) 0.020(3) 0.003(2) 0.000(2) 0.000(2) C5 0.014(3) 0.017(3) 0.020(3) 0.004(2) -0.002(2) 0.008(2) C6 0.016(3) 0.018(3) 0.018(3) 0.003(2) -0.001(2) 0.005(2) C7 0.024(3) 0.018(3) 0.018(3) 0.007(2) 0.009(2) 0.012(2) C8 0.018(3) 0.017(3) 0.017(3) 0.004(2) 0.005(2) 0.009(2) C9 0.022(3) 0.024(3) 0.021(3) 0.001(2) 0.001(2) 0.007(2) C10 0.015(3) 0.013(3) 0.013(3) 0.006(2) 0.004(2) 0.002(2) C11 0.016(3) 0.013(3) 0.014(3) 0.002(2) 0.001(2) 0.000(2) C12 0.020(3) 0.014(3) 0.016(3) 0.007(2) -0.001(2) 0.001(2) C13 0.020(3) 0.020(3) 0.019(3) 0.009(2) 0.005(2) 0.007(2) C14 0.017(3) 0.015(3) 0.013(3) 0.000(2) 0.001(2) 0.004(2) C15 0.018(3) 0.013(3) 0.017(3) 0.006(2) 0.002(2) 0.001(2) C16 0.010(3) 0.020(3) 0.022(3) 0.008(2) 0.009(2) 0.002(2) C17 0.016(3) 0.017(3) 0.028(3) 0.008(2) 0.010(2) 0.010(2) C18 0.017(3) 0.018(3) 0.021(3) 0.003(2) 0.007(2) 0.010(2) N1 0.013(2) 0.018(2) 0.012(2) 0.0040(18) -0.0009(17) 0.0043(17) N2 0.015(2) 0.012(2) 0.016(2) 0.0021(18) 0.0003(17) 0.0054(17) N3 0.015(2) 0.012(2) 0.018(2) 0.0059(18) 0.0042(18) 0.0044(17) N4 0.015(2) 0.010(2) 0.018(2) 0.0043(18) 0.0048(17) 0.0070(17) N5 0.014(2) 0.017(2) 0.013(2) 0.0017(18) 0.0018(17) 0.0067(18) N6 0.011(2) 0.014(2) 0.018(2) 0.0034(18) 0.0037(17) 0.0039(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 1.978(4) . ? Cu1 I1 2.5546(7) . ? Cu1 Cu3 2.5960(9) 1_645 y Cu1 I3 2.6353(7) 1_645 ? Cu1 Cu2 2.9509(10) 1_645 y Cu2 N5 2.008(4) . ? Cu2 I2 2.6450(8) . ? Cu2 I3 2.6721(8) . ? Cu2 I2 2.7339(8) 2_566 ? Cu2 Cu3 2.8135(9) . y Cu2 Cu1 2.9509(10) 1_465 ? Cu3 N3 2.008(4) . ? Cu3 Cu1 2.5960(9) 1_465 ? Cu3 I2 2.6629(8) . ? Cu3 I1 2.6945(8) 1_465 ? Cu3 I3 2.7720(8) . ? I1 Cu3 2.6945(8) 1_645 ? I2 Cu2 2.7339(8) 2_566 ? I3 Cu1 2.6353(7) 1_465 ? C1 C2 1.486(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.330(6) . ? C2 N2 1.360(7) . ? C3 C4 1.344(8) . ? C3 N1 1.391(7) . ? C3 H3 0.9500 . ? C4 N2 1.387(6) . ? C4 H4 0.9500 . ? C5 N2 1.468(6) . ? C5 C6 1.536(7) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.516(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.518(7) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N4 1.469(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.476(7) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N3 1.325(6) . ? C10 N4 1.353(6) . ? C11 C12 1.368(7) . ? C11 N4 1.385(6) . ? C11 H11 0.9500 . ? C12 N3 1.392(6) . ? C12 H12 0.9500 . ? C13 C14 1.482(7) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N5 1.323(7) . ? C14 N6 1.355(6) . ? C15 C16 1.341(8) . ? C15 N5 1.381(6) . ? C15 H15 0.9500 . ? C16 N6 1.402(6) . ? C16 H16 0.9500 . ? C17 N6 1.474(7) . ? C17 C18 1.516(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C18 1.528(10) 2_476 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? 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 I1 120.74(12) . . ? N1 Cu1 Cu3 175.79(12) . 1_645 ? I1 Cu1 Cu3 63.08(2) . 1_645 ? N1 Cu1 I3 113.59(12) . 1_645 ? I1 Cu1 I3 119.02(3) . 1_645 ? Cu3 Cu1 I3 63.99(2) 1_645 1_645 ? N1 Cu1 Cu2 115.29(12) . 1_645 ? I1 Cu1 Cu2 115.16(3) . 1_645 ? Cu3 Cu1 Cu2 60.56(2) 1_645 1_645 ? I3 Cu1 Cu2 56.816(19) 1_645 1_645 ? N5 Cu2 I2 107.60(12) . . ? N5 Cu2 I3 110.95(12) . . ? I2 Cu2 I3 117.47(3) . . ? N5 Cu2 I2 105.51(12) . 2_566 ? I2 Cu2 I2 110.46(3) . 2_566 ? I3 Cu2 I2 104.23(2) . 2_566 ? N5 Cu2 Cu3 117.61(12) . . ? I2 Cu2 Cu3 58.30(2) . . ? I3 Cu2 Cu3 60.64(2) . . ? I2 Cu2 Cu3 136.88(3) 2_566 . ? N5 Cu2 Cu1 71.10(12) . 1_465 ? I2 Cu2 Cu1 95.72(2) . 1_465 ? I3 Cu2 Cu1 55.63(2) . 1_465 ? I2 Cu2 Cu1 153.02(3) 2_566 1_465 ? Cu3 Cu2 Cu1 53.47(2) . 1_465 ? N3 Cu3 Cu1 141.42(13) . 1_465 ? N3 Cu3 I2 114.17(13) . . ? Cu1 Cu3 I2 104.36(3) 1_465 . ? N3 Cu3 I1 106.25(12) . 1_465 ? Cu1 Cu3 I1 57.71(2) 1_465 1_465 ? I2 Cu3 I1 107.99(2) . 1_465 ? N3 Cu3 I3 104.87(12) . . ? Cu1 Cu3 I3 58.70(2) 1_465 . ? I2 Cu3 I3 113.48(2) . . ? I1 Cu3 I3 109.79(2) 1_465 . ? N3 Cu3 Cu2 138.22(12) . . ? Cu1 Cu3 Cu2 65.98(3) 1_465 . ? I2 Cu3 Cu2 57.68(2) . . ? I1 Cu3 Cu2 115.25(3) 1_465 . ? I3 Cu3 Cu2 57.16(2) . . ? Cu1 I1 Cu3 59.21(2) . 1_645 ? Cu2 I2 Cu3 64.02(2) . . ? Cu2 I2 Cu2 69.54(3) . 2_566 ? Cu3 I2 Cu2 115.09(2) . 2_566 ? Cu1 I3 Cu2 67.55(2) 1_465 . ? Cu1 I3 Cu3 57.32(2) 1_465 . ? Cu2 I3 Cu3 62.20(2) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 110.1(4) . . ? N1 C2 C1 126.5(5) . . ? N2 C2 C1 123.4(5) . . ? C4 C3 N1 110.4(5) . . ? C4 C3 H3 124.8 . . ? N1 C3 H3 124.8 . . ? C3 C4 N2 105.7(5) . . ? C3 C4 H4 127.1 . . ? N2 C4 H4 127.1 . . ? N2 C5 C6 111.0(4) . . ? N2 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? N2 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 113.2(4) . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 113.9(4) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C7 111.9(4) . . ? N4 C8 H8A 109.2 . . ? C7 C8 H8A 109.2 . . ? N4 C8 H8B 109.2 . . ? C7 C8 H8B 109.2 . . ? H8A C8 H8B 107.9 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N4 110.8(4) . . ? N3 C10 C9 125.0(5) . . ? N4 C10 C9 124.2(5) . . ? C12 C11 N4 105.4(4) . . ? C12 C11 H11 127.3 . . ? N4 C11 H11 127.3 . . ? C11 C12 N3 109.6(5) . . ? C11 C12 H12 125.2 . . ? N3 C12 H12 125.2 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C14 N6 110.5(4) . . ? N5 C14 C13 126.5(5) . . ? N6 C14 C13 122.9(5) . . ? C16 C15 N5 110.1(5) . . ? C16 C15 H15 125.0 . . ? N5 C15 H15 125.0 . . ? C15 C16 N6 106.0(4) . . ? C15 C16 H16 127.0 . . ? N6 C16 H16 127.0 . . ? N6 C17 C18 110.9(4) . . ? N6 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? N6 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.0 . . ? C18 C18 C17 110.0(5) 2_476 . ? C18 C18 H18A 109.7 2_476 . ? C17 C18 H18A 109.7 . . ? C18 C18 H18B 109.7 2_476 . ? C17 C18 H18B 109.7 . . ? H18A C18 H18B 108.2 . . ? C2 N1 C3 105.9(4) . . ? C2 N1 Cu1 130.2(4) . . ? C3 N1 Cu1 123.2(3) . . ? C2 N2 C4 108.0(4) . . ? C2 N2 C5 126.2(4) . . ? C4 N2 C5 125.8(4) . . ? C10 N3 C12 106.0(4) . . ? C10 N3 Cu3 129.1(3) . . ? C12 N3 Cu3 124.6(3) . . ? C10 N4 C11 108.1(4) . . ? C10 N4 C8 127.0(4) . . ? C11 N4 C8 124.9(4) . . ? C14 N5 C15 106.5(4) . . ? C14 N5 Cu2 129.4(3) . . ? C15 N5 Cu2 124.1(4) . . ? C14 N6 C16 107.0(4) . . ? C14 N6 C17 125.4(4) . . ? C16 N6 C17 127.6(4) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.864 _refine_diff_density_min -0.888 _refine_diff_density_rms 0.212 _database_code_depnum_ccdc_archive 'CCDC 942895' ####################################################################### # # 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_3-160k _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 Cu3 I3 N6' _chemical_formula_weight 898.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2961(9) _cell_length_b 10.7386(10) _cell_length_c 11.9132(10) _cell_angle_alpha 106.7680(10) _cell_angle_beta 90.2070(10) _cell_angle_gamma 101.7260(10) _cell_volume 1232.14(19) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 4259 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 27.60 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 846 _exptl_absorpt_coefficient_mu 6.342 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4497 _exptl_absorpt_correction_T_max 0.5696 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6113 _diffrn_reflns_av_R_equivalents 0.0146 _diffrn_reflns_av_sigmaI/netI 0.0295 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4280 _reflns_number_gt 3930 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+2.0629P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4280 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0279 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_ref 0.0632 _refine_ls_wR_factor_gt 0.0598 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.70373(5) -0.59972(6) 0.20390(5) 0.02464(14) Uani 1 1 d . . . Cu2 Cu -0.08180(6) 0.51320(6) 0.39795(5) 0.02801(14) Uani 1 1 d . . . Cu3 Cu -0.16620(5) 0.24142(6) 0.26249(5) 0.02616(14) Uani 1 1 d . . . I1 I 0.57533(3) -0.83488(3) 0.18632(3) 0.02740(9) Uani 1 1 d . . . I2 I -0.15176(3) 0.32060(3) 0.49690(2) 0.02208(9) Uani 1 1 d . . . I3 I -0.04034(3) 0.43928(3) 0.16891(2) 0.02123(8) Uani 1 1 d . . . C1 C 0.3819(5) -0.5385(5) 0.2228(5) 0.0316(11) Uani 1 1 d . . . H1A H 0.3162 -0.5962 0.1600 0.047 Uiso 1 1 calc R . . H1B H 0.3383 -0.4787 0.2813 0.047 Uiso 1 1 calc R . . H1C H 0.4214 -0.5933 0.2603 0.047 Uiso 1 1 calc R . . C2 C 0.4883(4) -0.4581(4) 0.1722(4) 0.0216(9) Uani 1 1 d . . . C3 C 0.6751(4) -0.3750(4) 0.1138(4) 0.0240(10) Uani 1 1 d . . . H3 H 0.7665 -0.3586 0.0983 0.029 Uiso 1 1 calc R . . C4 C 0.5851(4) -0.3118(4) 0.0854(4) 0.0250(10) Uani 1 1 d . . . H4 H 0.6008 -0.2438 0.0478 0.030 Uiso 1 1 calc R . . C5 C 0.3414(5) -0.3238(5) 0.1127(4) 0.0261(10) Uani 1 1 d . . . H5A H 0.2660 -0.3993 0.1078 0.031 Uiso 1 1 calc R . . H5B H 0.3367 -0.2981 0.0396 0.031 Uiso 1 1 calc R . . C6 C 0.3290(5) -0.2063(5) 0.2178(4) 0.0285(11) Uani 1 1 d . . . H6A H 0.3402 -0.2303 0.2910 0.034 Uiso 1 1 calc R . . H6B H 0.4016 -0.1294 0.2194 0.034 Uiso 1 1 calc R . . C7 C 0.1962(5) -0.1653(5) 0.2150(4) 0.0276(11) Uani 1 1 d . . . H7A H 0.1854 -0.1053 0.2933 0.033 Uiso 1 1 calc R . . H7B H 0.1239 -0.2456 0.1995 0.033 Uiso 1 1 calc R . . C8 C 0.1819(4) -0.0951(5) 0.1228(4) 0.0228(10) Uani 1 1 d . . . H8A H 0.2590 -0.0200 0.1325 0.027 Uiso 1 1 calc R . . H8B H 0.1814 -0.1581 0.0435 0.027 Uiso 1 1 calc R . . C9 C 0.1475(5) 0.1755(5) 0.2820(4) 0.0313(11) Uani 1 1 d . . . H9A H 0.2127 0.2134 0.2346 0.047 Uiso 1 1 calc R . . H9B H 0.1915 0.1343 0.3304 0.047 Uiso 1 1 calc R . . H9C H 0.1090 0.2462 0.3330 0.047 Uiso 1 1 calc R . . C10 C 0.0400(4) 0.0728(4) 0.2030(4) 0.0202(9) Uani 1 1 d . . . C11 C -0.0602(4) -0.1123(4) 0.0732(4) 0.0235(10) Uani 1 1 d . . . H11 H -0.0784 -0.1981 0.0173 0.028 Uiso 1 1 calc R . . C12 C -0.1470(4) -0.0316(4) 0.1098(4) 0.0219(9) Uani 1 1 d . . . H12 H -0.2381 -0.0524 0.0830 0.026 Uiso 1 1 calc R . . C13 C -0.1110(5) 0.8179(5) 0.3607(4) 0.0287(11) Uani 1 1 d . . . H13A H -0.1492 0.8470 0.2995 0.043 Uiso 1 1 calc R . . H13B H -0.0481 0.7623 0.3265 0.043 Uiso 1 1 calc R . . H13C H -0.0645 0.8960 0.4231 0.043 Uiso 1 1 calc R . . C14 C -0.2192(4) 0.7398(4) 0.4105(4) 0.0209(9) Uani 1 1 d . . . C15 C -0.3377(4) 0.5910(5) 0.4782(4) 0.0249(10) Uani 1 1 d . . . H15 H -0.3652 0.5126 0.5013 0.030 Uiso 1 1 calc R . . C16 C -0.4083(4) 0.6860(5) 0.4887(4) 0.0258(10) Uani 1 1 d . . . H16 H -0.4932 0.6869 0.5194 0.031 Uiso 1 1 calc R . . C17 C -0.3672(5) 0.9035(5) 0.4351(4) 0.0268(10) Uani 1 1 d . . . H17A H -0.3899 0.8924 0.3515 0.032 Uiso 1 1 calc R . . H17B H -0.2895 0.9785 0.4623 0.032 Uiso 1 1 calc R . . C18 C -0.4827(5) 0.9361(4) 0.5059(4) 0.0244(10) Uani 1 1 d . . . H18A H -0.4604 0.9471 0.5896 0.029 Uiso 1 1 calc R . . H18B H -0.5609 0.8616 0.4786 0.029 Uiso 1 1 calc R . . N1 N 0.6150(3) -0.4675(4) 0.1688(3) 0.0198(8) Uani 1 1 d . . . N2 N 0.4662(3) -0.3657(4) 0.1221(3) 0.0212(8) Uani 1 1 d . . . N3 N -0.0844(3) 0.0843(3) 0.1910(3) 0.0194(8) Uani 1 1 d . . . N4 N 0.0589(3) -0.0449(4) 0.1332(3) 0.0200(8) Uani 1 1 d . . . N5 N -0.2196(4) 0.6245(4) 0.4290(3) 0.0223(8) Uani 1 1 d . . . N6 N -0.3322(3) 0.7823(4) 0.4456(3) 0.0207(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0230(3) 0.0269(3) 0.0287(3) 0.0121(3) 0.0032(2) 0.0101(2) Cu2 0.0262(3) 0.0258(3) 0.0367(3) 0.0122(3) 0.0111(3) 0.0115(2) Cu3 0.0262(3) 0.0245(3) 0.0289(3) 0.0051(2) 0.0027(2) 0.0121(2) I1 0.02017(16) 0.02757(17) 0.03558(18) 0.01209(14) 0.00217(12) 0.00361(12) I2 0.02194(15) 0.02350(16) 0.02145(16) 0.00870(12) 0.00214(11) 0.00330(12) I3 0.01982(15) 0.02012(16) 0.02277(16) 0.00471(12) 0.00449(11) 0.00434(11) C1 0.024(2) 0.039(3) 0.039(3) 0.019(2) 0.014(2) 0.011(2) C2 0.020(2) 0.023(2) 0.022(2) 0.0054(19) 0.0018(18) 0.0087(18) C3 0.020(2) 0.021(2) 0.031(3) 0.009(2) 0.0017(19) 0.0044(18) C4 0.025(2) 0.020(2) 0.030(3) 0.009(2) 0.0022(19) 0.0035(19) C5 0.026(2) 0.027(3) 0.026(2) 0.005(2) 0.0001(19) 0.013(2) C6 0.031(3) 0.028(3) 0.028(3) 0.008(2) -0.001(2) 0.011(2) C7 0.032(3) 0.028(3) 0.031(3) 0.013(2) 0.011(2) 0.016(2) C8 0.024(2) 0.025(2) 0.024(2) 0.009(2) 0.0078(18) 0.0129(19) C9 0.025(3) 0.027(3) 0.036(3) 0.003(2) -0.003(2) 0.004(2) C10 0.024(2) 0.016(2) 0.022(2) 0.0076(18) 0.0057(18) 0.0077(18) C11 0.027(2) 0.018(2) 0.025(2) 0.0073(19) 0.0031(19) 0.0023(18) C12 0.021(2) 0.019(2) 0.025(2) 0.0075(19) -0.0001(18) 0.0021(18) C13 0.024(2) 0.029(3) 0.037(3) 0.015(2) 0.010(2) 0.008(2) C14 0.024(2) 0.020(2) 0.021(2) 0.0057(19) 0.0035(18) 0.0090(18) C15 0.024(2) 0.022(2) 0.032(3) 0.012(2) 0.010(2) 0.0051(19) C16 0.018(2) 0.026(3) 0.037(3) 0.014(2) 0.012(2) 0.0044(19) C17 0.027(2) 0.023(2) 0.035(3) 0.011(2) 0.010(2) 0.0101(19) C18 0.027(2) 0.021(2) 0.028(2) 0.006(2) 0.0033(19) 0.0112(19) N1 0.0175(18) 0.0197(19) 0.0218(19) 0.0038(16) 0.0005(15) 0.0064(15) N2 0.0197(19) 0.022(2) 0.0215(19) 0.0037(16) -0.0003(15) 0.0075(15) N3 0.0242(19) 0.0162(19) 0.0165(18) 0.0023(15) 0.0009(15) 0.0049(15) N4 0.0205(19) 0.0204(19) 0.0215(19) 0.0073(16) 0.0045(15) 0.0077(15) N5 0.0219(19) 0.022(2) 0.024(2) 0.0073(16) 0.0042(15) 0.0084(16) N6 0.0169(18) 0.0196(19) 0.029(2) 0.0093(16) 0.0066(15) 0.0079(15) _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 1.973(4) . ? Cu1 I1 2.5503(7) . ? Cu1 Cu3 2.6076(8) 1_645 y Cu1 I3 2.6369(6) 1_645 ? Cu1 Cu2 2.9914(9) 1_645 y Cu2 N5 2.004(4) . ? Cu2 I2 2.6445(7) . ? Cu2 I3 2.6748(7) . ? Cu2 I2 2.7351(7) 2_566 ? Cu2 Cu3 2.8493(8) . y Cu2 Cu1 2.9914(9) 1_465 ? Cu3 N3 2.009(4) . ? Cu3 Cu1 2.6076(8) 1_465 ? Cu3 I2 2.6681(7) . ? Cu3 I1 2.6915(7) 1_465 ? Cu3 I3 2.7739(7) . ? I1 Cu3 2.6915(7) 1_645 ? I2 Cu2 2.7351(7) 2_566 ? I3 Cu1 2.6369(6) 1_465 ? C1 C2 1.493(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 N1 1.329(5) . ? C2 N2 1.349(6) . ? C3 C4 1.349(7) . ? C3 N1 1.388(6) . ? C3 H3 0.9500 . ? C4 N2 1.374(6) . ? C4 H4 0.9500 . ? C5 N2 1.460(6) . ? C5 C6 1.527(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.523(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.522(6) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N4 1.466(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.492(6) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N3 1.322(6) . ? C10 N4 1.351(5) . ? C11 C12 1.357(6) . ? C11 N4 1.368(6) . ? C11 H11 0.9500 . ? C12 N3 1.369(5) . ? C12 H12 0.9500 . ? C13 C14 1.486(6) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 N5 1.317(6) . ? C14 N6 1.359(5) . ? C15 C16 1.347(7) . ? C15 N5 1.379(6) . ? C15 H15 0.9500 . ? C16 N6 1.388(6) . ? C16 H16 0.9500 . ? C17 N6 1.457(6) . ? C17 C18 1.501(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C18 1.529(9) 2_476 ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? 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 I1 121.12(10) . . ? N1 Cu1 Cu3 175.38(11) . 1_645 ? I1 Cu1 Cu3 62.90(2) . 1_645 ? N1 Cu1 I3 113.76(10) . 1_645 ? I1 Cu1 I3 119.07(2) . 1_645 ? Cu3 Cu1 I3 63.862(19) 1_645 1_645 ? N1 Cu1 Cu2 114.67(10) . 1_645 ? I1 Cu1 Cu2 115.10(2) . 1_645 ? Cu3 Cu1 Cu2 60.72(2) 1_645 1_645 ? I3 Cu1 Cu2 56.326(17) 1_645 1_645 ? N5 Cu2 I2 107.75(11) . . ? N5 Cu2 I3 110.58(11) . . ? I2 Cu2 I3 116.77(2) . . ? N5 Cu2 I2 105.92(11) . 2_566 ? I2 Cu2 I2 110.57(2) . 2_566 ? I3 Cu2 I2 104.74(2) . 2_566 ? N5 Cu2 Cu3 117.33(11) . . ? I2 Cu2 Cu3 57.968(19) . . ? I3 Cu2 Cu3 60.185(18) . . ? I2 Cu2 Cu3 136.73(2) 2_566 . ? N5 Cu2 Cu1 71.18(11) . 1_465 ? I2 Cu2 Cu1 95.05(2) . 1_465 ? I3 Cu2 Cu1 55.126(17) . 1_465 ? I2 Cu2 Cu1 153.44(3) 2_566 1_465 ? Cu3 Cu2 Cu1 52.966(19) . 1_465 ? N3 Cu3 Cu1 141.27(11) . 1_465 ? N3 Cu3 I2 114.48(10) . . ? Cu1 Cu3 I2 104.20(2) 1_465 . ? N3 Cu3 I1 106.18(10) . 1_465 ? Cu1 Cu3 I1 57.510(19) 1_465 1_465 ? I2 Cu3 I1 108.11(2) . 1_465 ? N3 Cu3 I3 105.38(10) . . ? Cu1 Cu3 I3 58.581(19) 1_465 . ? I2 Cu3 I3 112.67(2) . . ? I1 Cu3 I3 109.78(2) 1_465 . ? N3 Cu3 Cu2 138.22(10) . . ? Cu1 Cu3 Cu2 66.31(2) 1_465 . ? I2 Cu3 Cu2 57.164(18) . . ? I1 Cu3 Cu2 115.33(2) 1_465 . ? I3 Cu3 Cu2 56.786(18) . . ? Cu1 I1 Cu3 59.593(19) . 1_645 ? Cu2 I2 Cu3 64.87(2) . . ? Cu2 I2 Cu2 69.43(2) . 2_566 ? Cu3 I2 Cu2 115.43(2) . 2_566 ? Cu1 I3 Cu2 68.548(19) 1_465 . ? Cu1 I3 Cu3 57.557(17) 1_465 . ? Cu2 I3 Cu3 63.029(18) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 111.0(4) . . ? N1 C2 C1 125.6(4) . . ? N2 C2 C1 123.4(4) . . ? C4 C3 N1 110.2(4) . . ? C4 C3 H3 124.9 . . ? N1 C3 H3 124.9 . . ? C3 C4 N2 106.0(4) . . ? C3 C4 H4 127.0 . . ? N2 C4 H4 127.0 . . ? N2 C5 C6 111.5(4) . . ? N2 C5 H5A 109.3 . . ? C6 C5 H5A 109.3 . . ? N2 C5 H5B 109.3 . . ? C6 C5 H5B 109.3 . . ? H5A C5 H5B 108.0 . . ? C7 C6 C5 113.0(4) . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 113.8(4) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N4 C8 C7 111.2(3) . . ? N4 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? N4 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N4 111.2(4) . . ? N3 C10 C9 125.3(4) . . ? N4 C10 C9 123.4(4) . . ? C12 C11 N4 106.0(4) . . ? C12 C11 H11 127.0 . . ? N4 C11 H11 127.0 . . ? C11 C12 N3 110.2(4) . . ? C11 C12 H12 124.9 . . ? N3 C12 H12 124.9 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C14 N6 110.9(4) . . ? N5 C14 C13 126.3(4) . . ? N6 C14 C13 122.8(4) . . ? C16 C15 N5 109.8(4) . . ? C16 C15 H15 125.1 . . ? N5 C15 H15 125.1 . . ? C15 C16 N6 106.3(4) . . ? C15 C16 H16 126.8 . . ? N6 C16 H16 126.8 . . ? N6 C17 C18 111.9(4) . . ? N6 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? N6 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C18 111.0(5) . 2_476 ? C17 C18 H18A 109.4 . . ? C18 C18 H18A 109.4 2_476 . ? C17 C18 H18B 109.4 . . ? C18 C18 H18B 109.4 2_476 . ? H18A C18 H18B 108.0 . . ? C2 N1 C3 105.0(4) . . ? C2 N1 Cu1 130.6(3) . . ? C3 N1 Cu1 123.5(3) . . ? C2 N2 C4 107.7(4) . . ? C2 N2 C5 127.3(4) . . ? C4 N2 C5 125.0(4) . . ? C10 N3 C12 105.4(4) . . ? C10 N3 Cu3 128.9(3) . . ? C12 N3 Cu3 125.5(3) . . ? C10 N4 C11 107.2(4) . . ? C10 N4 C8 127.6(4) . . ? C11 N4 C8 125.2(4) . . ? C14 N5 C15 106.2(4) . . ? C14 N5 Cu2 129.8(3) . . ? C15 N5 Cu2 124.0(3) . . ? C14 N6 C16 106.7(4) . . ? C14 N6 C17 125.9(4) . . ? C16 N6 C17 127.3(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.089 _refine_diff_density_min -0.703 _refine_diff_density_rms 0.121 _database_code_depnum_ccdc_archive 'CCDC 942896' ####################################################################### # # 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_3-220k _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 Cu3 I3 N6' _chemical_formula_weight 898.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.352(2) _cell_length_b 10.760(2) _cell_length_c 11.977(2) _cell_angle_alpha 106.782(3) _cell_angle_beta 90.335(3) _cell_angle_gamma 101.715(3) _cell_volume 1247.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 3116 _cell_measurement_theta_min 4.531 _cell_measurement_theta_max 54.539 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 846 _exptl_absorpt_coefficient_mu 6.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4535 _exptl_absorpt_correction_T_max 0.5732 _exptl_absorpt_process_details sadabs _exptl_special_details ? _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6102 _diffrn_reflns_av_R_equivalents 0.0173 _diffrn_reflns_av_sigmaI/netI 0.0376 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4295 _reflns_number_gt 3652 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+2.1920P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4295 _refine_ls_number_parameters 271 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0892 _refine_ls_wR_factor_gt 0.0780 _refine_ls_goodness_of_fit_ref 1.095 _refine_ls_restrained_S_all 1.095 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.70147(8) -0.60188(8) 0.20213(7) 0.0340(2) Uani 1 1 d . . . Cu2 Cu -0.08211(8) 0.51502(8) 0.39906(8) 0.0389(2) Uani 1 1 d . . . Cu3 Cu -0.16783(8) 0.23881(8) 0.26179(8) 0.0360(2) Uani 1 1 d . . . I1 I 0.57478(4) -0.83712(5) 0.18587(4) 0.03771(14) Uani 1 1 d . . . I2 I -0.15216(4) 0.32061(4) 0.49577(4) 0.02930(13) Uani 1 1 d . . . I3 I -0.04287(4) 0.43902(4) 0.17013(3) 0.02876(12) Uani 1 1 d . . . C1 C 0.3806(7) -0.5417(8) 0.2207(7) 0.0456(19) Uani 1 1 d . . . H1A H 0.3166 -0.5980 0.1578 0.068 Uiso 1 1 calc R . . H1B H 0.3368 -0.4843 0.2787 0.068 Uiso 1 1 calc R . . H1C H 0.4197 -0.5967 0.2566 0.068 Uiso 1 1 calc R . . C2 C 0.4861(6) -0.4591(6) 0.1729(6) 0.0295(15) Uani 1 1 d . . . C3 C 0.6734(6) -0.3756(6) 0.1165(6) 0.0312(15) Uani 1 1 d . . . H3 H 0.7637 -0.3587 0.1028 0.037 Uiso 1 1 calc R . . C4 C 0.5823(7) -0.3117(7) 0.0879(6) 0.0372(16) Uani 1 1 d . . . H4 H 0.5972 -0.2446 0.0508 0.045 Uiso 1 1 calc R . . C5 C 0.3388(6) -0.3254(7) 0.1128(6) 0.0339(16) Uani 1 1 d . . . H5A H 0.2649 -0.4007 0.1069 0.041 Uiso 1 1 calc R . . H5B H 0.3351 -0.2993 0.0411 0.041 Uiso 1 1 calc R . . C6 C 0.3260(7) -0.2102(7) 0.2172(7) 0.0419(18) Uani 1 1 d . . . H6A H 0.3982 -0.1342 0.2206 0.050 Uiso 1 1 calc R . . H6B H 0.3350 -0.2353 0.2888 0.050 Uiso 1 1 calc R . . C7 C 0.1938(7) -0.1684(7) 0.2125(6) 0.0355(16) Uani 1 1 d . . . H7A H 0.1224 -0.2478 0.1957 0.043 Uiso 1 1 calc R . . H7B H 0.1821 -0.1101 0.2897 0.043 Uiso 1 1 calc R . . C8 C 0.1805(6) -0.0969(7) 0.1222(6) 0.0317(15) Uani 1 1 d . . . H8A H 0.2570 -0.0231 0.1323 0.038 Uiso 1 1 calc R . . H8B H 0.1794 -0.1584 0.0437 0.038 Uiso 1 1 calc R . . C9 C 0.1442(7) 0.1736(7) 0.2816(7) 0.0440(18) Uani 1 1 d . . . H9A H 0.2085 0.2111 0.2351 0.066 Uiso 1 1 calc R . . H9B H 0.1875 0.1334 0.3297 0.066 Uiso 1 1 calc R . . H9C H 0.1059 0.2434 0.3312 0.066 Uiso 1 1 calc R . . C10 C 0.0391(6) 0.0718(6) 0.2036(5) 0.0269(14) Uani 1 1 d . . . C11 C -0.0613(6) -0.1141(6) 0.0726(6) 0.0336(16) Uani 1 1 d . . . H11 H -0.0789 -0.1990 0.0178 0.040 Uiso 1 1 calc R . . C12 C -0.1466(6) -0.0337(6) 0.1083(6) 0.0287(14) Uani 1 1 d . . . H12 H -0.2359 -0.0543 0.0808 0.034 Uiso 1 1 calc R . . C13 C -0.1115(6) 0.8185(7) 0.3625(7) 0.0387(17) Uani 1 1 d . . . H13A H -0.1488 0.8473 0.3021 0.058 Uiso 1 1 calc R . . H13B H -0.0491 0.7642 0.3292 0.058 Uiso 1 1 calc R . . H13C H -0.0665 0.8957 0.4245 0.058 Uiso 1 1 calc R . . C14 C -0.2194(6) 0.7394(6) 0.4109(5) 0.0251(13) Uani 1 1 d . . . C15 C -0.3382(6) 0.5923(6) 0.4773(5) 0.0284(14) Uani 1 1 d . . . H15 H -0.3651 0.5146 0.4997 0.034 Uiso 1 1 calc R . . C16 C -0.4085(7) 0.6860(7) 0.4878(6) 0.0378(17) Uani 1 1 d . . . H16 H -0.4923 0.6863 0.5176 0.045 Uiso 1 1 calc R . . C17 C -0.3685(7) 0.9042(6) 0.4348(7) 0.0370(17) Uani 1 1 d . . . H17A H -0.3923 0.8925 0.3525 0.044 Uiso 1 1 calc R . . H17B H -0.2920 0.9786 0.4606 0.044 Uiso 1 1 calc R . . C18 C -0.4820(6) 0.9363(6) 0.5061(6) 0.0312(15) Uani 1 1 d . . . H18A H -0.4584 0.9481 0.5885 0.037 Uiso 1 1 calc R . . H18B H -0.5588 0.8622 0.4802 0.037 Uiso 1 1 calc R . . N1 N 0.6122(5) -0.4682(5) 0.1681(4) 0.0277(12) Uani 1 1 d . . . N2 N 0.4649(5) -0.3657(5) 0.1246(5) 0.0324(13) Uani 1 1 d . . . N3 N -0.0857(5) 0.0825(5) 0.1901(4) 0.0265(12) Uani 1 1 d . . . N4 N 0.0580(5) -0.0452(5) 0.1338(4) 0.0260(11) Uani 1 1 d . . . N5 N -0.2207(5) 0.6259(5) 0.4290(4) 0.0275(12) Uani 1 1 d . . . N6 N -0.3327(5) 0.7831(5) 0.4457(5) 0.0285(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0319(4) 0.0373(5) 0.0388(5) 0.0163(4) 0.0042(4) 0.0137(4) Cu2 0.0366(5) 0.0363(5) 0.0510(6) 0.0170(4) 0.0158(4) 0.0174(4) Cu3 0.0361(5) 0.0331(5) 0.0403(5) 0.0065(4) 0.0029(4) 0.0170(4) I1 0.0276(2) 0.0376(3) 0.0491(3) 0.0164(2) 0.0023(2) 0.00445(19) I2 0.0297(2) 0.0308(2) 0.0284(2) 0.01144(18) 0.00230(17) 0.00485(17) I3 0.0270(2) 0.0270(2) 0.0308(2) 0.00606(18) 0.00577(17) 0.00612(17) C1 0.036(4) 0.049(5) 0.062(5) 0.029(4) 0.016(4) 0.014(3) C2 0.023(3) 0.028(3) 0.032(4) 0.004(3) 0.004(3) 0.003(3) C3 0.027(3) 0.027(3) 0.041(4) 0.012(3) -0.005(3) 0.004(3) C4 0.036(4) 0.025(4) 0.049(4) 0.010(3) 0.002(3) 0.005(3) C5 0.032(4) 0.034(4) 0.037(4) 0.006(3) -0.002(3) 0.017(3) C6 0.042(4) 0.039(4) 0.044(4) 0.008(3) 0.004(3) 0.013(3) C7 0.039(4) 0.035(4) 0.042(4) 0.017(3) 0.013(3) 0.022(3) C8 0.029(3) 0.036(4) 0.034(4) 0.011(3) 0.007(3) 0.016(3) C9 0.038(4) 0.037(4) 0.053(5) 0.005(4) -0.004(3) 0.012(3) C10 0.032(3) 0.023(3) 0.026(3) 0.004(3) 0.004(3) 0.008(3) C11 0.038(4) 0.024(3) 0.031(4) 0.002(3) 0.007(3) -0.002(3) C12 0.026(3) 0.025(3) 0.037(4) 0.012(3) -0.004(3) 0.006(3) C13 0.025(3) 0.047(4) 0.058(5) 0.032(4) 0.016(3) 0.015(3) C14 0.022(3) 0.028(3) 0.028(3) 0.009(3) 0.004(3) 0.009(3) C15 0.027(3) 0.029(3) 0.034(4) 0.014(3) 0.007(3) 0.008(3) C16 0.029(4) 0.032(4) 0.053(4) 0.013(3) 0.021(3) 0.005(3) C17 0.041(4) 0.026(4) 0.050(4) 0.017(3) 0.016(3) 0.013(3) C18 0.032(3) 0.030(4) 0.040(4) 0.015(3) 0.003(3) 0.018(3) N1 0.022(3) 0.031(3) 0.030(3) 0.006(2) -0.001(2) 0.008(2) N2 0.031(3) 0.025(3) 0.037(3) 0.000(2) 0.001(2) 0.010(2) N3 0.028(3) 0.022(3) 0.030(3) 0.007(2) 0.000(2) 0.008(2) N4 0.028(3) 0.027(3) 0.026(3) 0.009(2) 0.003(2) 0.011(2) N5 0.028(3) 0.026(3) 0.030(3) 0.007(2) 0.004(2) 0.010(2) N6 0.022(3) 0.030(3) 0.037(3) 0.013(2) 0.007(2) 0.010(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N1 1.991(5) . ? Cu1 I1 2.5551(11) . ? Cu1 Cu3 2.6301(12) 1_645 y Cu1 I3 2.6421(10) 1_645 ? Cu1 Cu2 3.0406(13) 1_645 y Cu2 N5 2.017(5) . ? Cu2 I2 2.6527(11) . ? Cu2 I3 2.6842(11) . ? Cu2 I2 2.7444(11) 2_566 ? Cu2 Cu3 2.9006(13) . y Cu2 Cu1 3.0406(13) 1_465 ? Cu3 N3 2.011(5) . ? Cu3 Cu1 2.6301(13) 1_465 ? Cu3 I2 2.6772(11) . ? Cu3 I1 2.6930(11) 1_465 ? Cu3 I3 2.7874(10) . ? I1 Cu3 2.6930(11) 1_645 ? I2 Cu2 2.7444(11) 2_566 ? I3 Cu1 2.6421(10) 1_465 ? C1 C2 1.489(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C1 H1C 0.9700 . ? C2 N1 1.329(8) . ? C2 N2 1.348(9) . ? C3 C4 1.369(10) . ? C3 N1 1.371(8) . ? C3 H3 0.9400 . ? C4 N2 1.369(8) . ? C4 H4 0.9400 . ? C5 N2 1.475(8) . ? C5 C6 1.514(9) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C6 C7 1.530(9) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C7 C8 1.516(9) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 N4 1.477(8) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C9 C10 1.472(9) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 N3 1.333(8) . ? C10 N4 1.348(8) . ? C11 C12 1.346(9) . ? C11 N4 1.384(8) . ? C11 H11 0.9400 . ? C12 N3 1.373(8) . ? C12 H12 0.9400 . ? C13 C14 1.488(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 H13C 0.9700 . ? C14 N5 1.298(8) . ? C14 N6 1.374(7) . ? C15 C16 1.337(9) . ? C15 N5 1.376(8) . ? C15 H15 0.9400 . ? C16 N6 1.391(8) . ? C16 H16 0.9400 . ? C17 N6 1.465(8) . ? C17 C18 1.495(9) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C18 C18 1.538(12) 2_476 ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Cu1 I1 121.57(15) . . ? N1 Cu1 Cu3 174.93(15) . 1_645 ? I1 Cu1 Cu3 62.56(3) . 1_645 ? N1 Cu1 I3 113.91(15) . 1_645 ? I1 Cu1 I3 119.15(3) . 1_645 ? Cu3 Cu1 I3 63.84(3) 1_645 1_645 ? N1 Cu1 Cu2 113.91(15) . 1_645 ? I1 Cu1 Cu2 114.97(4) . 1_645 ? Cu3 Cu1 Cu2 61.02(3) 1_645 1_645 ? I3 Cu1 Cu2 55.84(3) 1_645 1_645 ? N5 Cu2 I2 107.90(15) . . ? N5 Cu2 I3 110.26(15) . . ? I2 Cu2 I3 115.85(4) . . ? N5 Cu2 I2 106.82(15) . 2_566 ? I2 Cu2 I2 110.51(4) . 2_566 ? I3 Cu2 I2 105.15(3) . 2_566 ? N5 Cu2 Cu3 116.96(15) . . ? I2 Cu2 Cu3 57.44(3) . . ? I3 Cu2 Cu3 59.73(3) . . ? I2 Cu2 Cu3 136.21(4) 2_566 . ? N5 Cu2 Cu1 71.25(15) . 1_465 ? I2 Cu2 Cu1 94.35(3) . 1_465 ? I3 Cu2 Cu1 54.54(3) . 1_465 ? I2 Cu2 Cu1 153.89(4) 2_566 1_465 ? Cu3 Cu2 Cu1 52.49(3) . 1_465 ? N3 Cu3 Cu1 140.88(16) . 1_465 ? N3 Cu3 I2 115.03(15) . . ? Cu1 Cu3 I2 104.06(3) 1_465 . ? N3 Cu3 I1 106.43(15) . 1_465 ? Cu1 Cu3 I1 57.36(3) 1_465 1_465 ? I2 Cu3 I1 108.27(3) . 1_465 ? N3 Cu3 I3 105.52(15) . . ? Cu1 Cu3 I3 58.29(3) 1_465 . ? I2 Cu3 I3 111.68(3) . . ? I1 Cu3 I3 109.71(3) 1_465 . ? N3 Cu3 Cu2 138.00(15) . . ? Cu1 Cu3 Cu2 66.49(4) 1_465 . ? I2 Cu3 Cu2 56.62(3) . . ? I1 Cu3 Cu2 115.26(3) 1_465 . ? I3 Cu3 Cu2 56.27(3) . . ? Cu1 I1 Cu3 60.08(3) . 1_645 ? Cu2 I2 Cu3 65.94(3) . . ? Cu2 I2 Cu2 69.49(4) . 2_566 ? Cu3 I2 Cu2 115.79(3) . 2_566 ? Cu1 I3 Cu2 69.62(3) 1_465 . ? Cu1 I3 Cu3 57.87(3) 1_465 . ? Cu2 I3 Cu3 63.99(3) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 N2 110.2(5) . . ? N1 C2 C1 125.9(6) . . ? N2 C2 C1 123.9(6) . . ? C4 C3 N1 109.3(6) . . ? C4 C3 H3 125.4 . . ? N1 C3 H3 125.4 . . ? C3 C4 N2 105.8(6) . . ? C3 C4 H4 127.1 . . ? N2 C4 H4 127.1 . . ? N2 C5 C6 110.3(5) . . ? N2 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? N2 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C5 C6 C7 112.6(6) . . ? C5 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? C5 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C8 C7 C6 114.6(6) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N4 C8 C7 111.0(5) . . ? N4 C8 H8A 109.4 . . ? C7 C8 H8A 109.4 . . ? N4 C8 H8B 109.4 . . ? C7 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N3 C10 N4 110.7(5) . . ? N3 C10 C9 125.6(6) . . ? N4 C10 C9 123.8(6) . . ? C12 C11 N4 105.4(5) . . ? C12 C11 H11 127.3 . . ? N4 C11 H11 127.3 . . ? C11 C12 N3 111.0(6) . . ? C11 C12 H12 124.5 . . ? N3 C12 H12 124.5 . . ? C14 C13 H13A 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C14 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N5 C14 N6 111.0(5) . . ? N5 C14 C13 126.9(6) . . ? N6 C14 C13 122.1(6) . . ? C16 C15 N5 110.2(6) . . ? C16 C15 H15 124.9 . . ? N5 C15 H15 124.9 . . ? C15 C16 N6 106.2(5) . . ? C15 C16 H16 126.9 . . ? N6 C16 H16 126.9 . . ? N6 C17 C18 111.5(5) . . ? N6 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? N6 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C17 C18 C18 110.8(7) . 2_476 ? C17 C18 H18A 109.5 . . ? C18 C18 H18A 109.5 2_476 . ? C17 C18 H18B 109.5 . . ? C18 C18 H18B 109.5 2_476 . ? H18A C18 H18B 108.1 . . ? C2 N1 C3 106.5(6) . . ? C2 N1 Cu1 130.2(5) . . ? C3 N1 Cu1 122.7(4) . . ? C2 N2 C4 108.2(5) . . ? C2 N2 C5 127.1(6) . . ? C4 N2 C5 124.7(6) . . ? C10 N3 C12 105.3(5) . . ? C10 N3 Cu3 128.5(4) . . ? C12 N3 Cu3 126.1(4) . . ? C10 N4 C11 107.7(5) . . ? C10 N4 C8 128.3(5) . . ? C11 N4 C8 124.0(5) . . ? C14 N5 C15 106.6(5) . . ? C14 N5 Cu2 129.3(4) . . ? C15 N5 Cu2 124.1(4) . . ? C14 N6 C16 106.0(5) . . ? C14 N6 C17 126.6(5) . . ? C16 N6 C17 127.3(5) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.965 _refine_diff_density_min -0.712 _refine_diff_density_rms 0.158 _database_code_depnum_ccdc_archive 'CCDC 942897'