# 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_Compound1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H18 N2), I6 Pb' _chemical_formula_sum 'C16 H36 I6 N4 Pb' _chemical_formula_weight 1234.93 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting cubic _symmetry_space_group_name_H-M Pa-3 _symmetry_space_group_name_hall '-P 2ac 2ab 3' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 'z, x, y' 'z+1/2, -x+1/2, -y' '-z+1/2, -x, y+1/2' '-z, x+1/2, -y+1/2' 'y, z, x' '-y, z+1/2, -x+1/2' 'y+1/2, -z+1/2, -x' '-y+1/2, -z, x+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' '-z, -x, -y' '-z-1/2, x-1/2, y' 'z-1/2, x, -y-1/2' 'z, -x-1/2, y-1/2' '-y, -z, -x' 'y, -z-1/2, x-1/2' '-y-1/2, z-1/2, x' 'y-1/2, z, -x-1/2' _cell_length_a 14.6567(3) _cell_length_b 14.6567(3) _cell_length_c 14.6567(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3148.54(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7335 _cell_measurement_theta_min 2.4061 _cell_measurement_theta_max 27.4835 _exptl_crystal_description block _exptl_crystal_colour colourless _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 2.605 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2168 _exptl_absorpt_coefficient_mu 11.250 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2832 _exptl_absorpt_correction_T_max 0.3992 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Ultrax-Saturn 70' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19929 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0124 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 25.49 _reflns_number_total 986 _reflns_number_gt 985 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0275P)^2^+10.9889P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00171(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 986 _refine_ls_number_parameters 43 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0760 _refine_ls_goodness_of_fit_ref 1.341 _refine_ls_restrained_S_all 1.341 _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 Pb1 Pb 0.0000 1.0000 0.5000 0.03936(8) Uani 1 6 d S . . I1 I 0.213464(18) 1.038060(19) 0.459967(17) 0.04583(8) Uani 1 1 d . . . N2 N 0.3530(2) 0.6470(2) 0.1470(2) 0.0422(12) Uani 1 3 d S . . N1 N 0.2520(2) 0.7480(2) 0.2480(2) 0.0414(13) Uani 1 3 d S . . C2 C 0.2113(3) 0.6532(3) 0.2373(3) 0.0489(11) Uani 1 1 d . . . H2A H 0.1945 0.6293 0.2967 0.059 Uiso 1 1 calc R . . H2B H 0.1566 0.6565 0.2001 0.059 Uiso 1 1 calc R . . C3 C 0.2796(3) 0.5908(3) 0.1928(3) 0.0517(11) Uani 1 1 d . . . H3A H 0.2492 0.5527 0.1480 0.062 Uiso 1 1 calc R . . H3B H 0.3068 0.5513 0.2384 0.062 Uiso 1 1 calc R . . C4 C 0.4123(3) 0.5877(3) 0.0877(3) 0.0579(19) Uani 1 3 d S . . H4A H 0.4582 0.6245 0.0590 0.087 Uiso 0.33 1 calc PR . . H4B H 0.3755 0.5590 0.0418 0.087 Uiso 0.33 1 calc PR . . H4C H 0.4410 0.5418 0.1245 0.087 Uiso 0.33 1 calc PR . . C1 C 0.1939(4) 0.8061(4) 0.3061(4) 0.072(2) Uani 1 3 d S . . H1A H 0.2211 0.8654 0.3118 0.108 Uiso 0.33 1 calc PR . . H1B H 0.1882 0.7789 0.3654 0.108 Uiso 0.33 1 calc PR . . H1C H 0.1346 0.8118 0.2789 0.108 Uiso 0.33 1 calc PR . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.03936(8) 0.03936(8) 0.03936(8) 0.00073(8) -0.00073(8) -0.00073(8) I1 0.04461(13) 0.05282(15) 0.04005(13) 0.00944(11) 0.00133(11) 0.00197(11) N2 0.0422(12) 0.0422(12) 0.0422(12) 0.0066(15) -0.0066(15) -0.0066(15) N1 0.0414(13) 0.0414(13) 0.0414(13) 0.0064(15) -0.0064(15) -0.0064(15) C2 0.049(2) 0.054(2) 0.044(2) 0.0126(18) -0.0082(17) -0.0228(18) C3 0.070(3) 0.046(2) 0.0387(19) 0.0052(17) -0.0077(19) -0.0270(19) C4 0.0579(19) 0.0579(19) 0.0579(19) 0.002(2) -0.002(2) -0.002(2) C1 0.072(2) 0.072(2) 0.072(2) -0.001(3) 0.001(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 Pb1 I1 3.2317(3) 22_476 ? Pb1 I1 3.2317(3) 13_576 ? Pb1 I1 3.2317(3) 7_564 ? Pb1 I1 3.2317(3) . ? Pb1 I1 3.2317(3) 19_567 ? Pb1 I1 3.2317(3) 10_655 ? N2 C4 1.504(10) . ? N2 C3 1.513(5) 10_655 ? N2 C3 1.513(5) . ? N2 C3 1.513(5) 7_564 ? N1 C1 1.474(11) . ? N1 C2 1.521(4) 10_655 ? N1 C2 1.521(4) . ? N1 C2 1.521(4) 7_564 ? C2 C3 1.505(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I1 Pb1 I1 91.299(7) 22_476 13_576 ? I1 Pb1 I1 88.701(7) 22_476 7_564 ? I1 Pb1 I1 88.701(7) 13_576 7_564 ? I1 Pb1 I1 88.701(7) 22_476 . ? I1 Pb1 I1 180.000(2) 13_576 . ? I1 Pb1 I1 91.299(7) 7_564 . ? I1 Pb1 I1 91.299(7) 22_476 19_567 ? I1 Pb1 I1 91.299(7) 13_576 19_567 ? I1 Pb1 I1 180.0 7_564 19_567 ? I1 Pb1 I1 88.701(7) . 19_567 ? I1 Pb1 I1 180.0 22_476 10_655 ? I1 Pb1 I1 88.701(7) 13_576 10_655 ? I1 Pb1 I1 91.299(7) 7_564 10_655 ? I1 Pb1 I1 91.299(7) . 10_655 ? I1 Pb1 I1 88.701(7) 19_567 10_655 ? C4 N2 C3 110.7(3) . 10_655 ? C4 N2 C3 110.7(3) . . ? C3 N2 C3 108.2(3) 10_655 . ? C4 N2 C3 110.7(3) . 7_564 ? C3 N2 C3 108.2(3) 10_655 7_564 ? C3 N2 C3 108.2(3) . 7_564 ? C1 N1 C2 111.1(3) . 10_655 ? C1 N1 C2 111.1(3) . . ? C2 N1 C2 107.7(3) 10_655 . ? C1 N1 C2 111.1(3) . 7_564 ? C2 N1 C2 107.7(3) 10_655 7_564 ? C2 N1 C2 107.7(3) . 7_564 ? C3 C2 N1 109.8(4) . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2B 109.7 . . ? N1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 N2 109.6(4) . . ? C2 C3 H3A 109.8 . . ? N2 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? N2 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N2 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? N2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? N1 C1 H1A 109.5 . . ? N1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? N1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.49 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.503 _refine_diff_density_min -0.552 _refine_diff_density_rms 0.099 _database_code_depnum_ccdc_archive 'CCDC 957317' ####################################################################### # # 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_Compound2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H22 N2, 0.5(I10 Pb3)' _chemical_formula_sum 'C20 H44 I10 N4 Pb3' _chemical_formula_weight 2231.19 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' 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' Pb Pb -3.3944 10.1111 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.3555(6) _cell_length_b 20.2788(12) _cell_length_c 14.7688(10) _cell_angle_alpha 90.00 _cell_angle_beta 126.541(4) _cell_angle_gamma 90.00 _cell_volume 2251.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6377 _cell_measurement_theta_min 2.6403 _cell_measurement_theta_max 27.4816 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1936 _exptl_absorpt_coefficient_mu 18.065 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1228 _exptl_absorpt_correction_T_max 0.3259 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Ultrax-Saturn 70' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16765 _diffrn_reflns_av_R_equivalents 0.0553 _diffrn_reflns_av_sigmaI/netI 0.0457 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.84 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4150 _reflns_number_gt 3406 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0260P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4150 _refine_ls_number_parameters 169 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0298 _refine_ls_wR_factor_ref 0.0609 _refine_ls_wR_factor_gt 0.0588 _refine_ls_goodness_of_fit_ref 0.948 _refine_ls_restrained_S_all 0.948 _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 Pb1 Pb -0.16731(2) 0.446729(9) 0.329707(14) 0.03687(6) Uani 1 1 d . . . Pb2 Pb -0.5000 0.5000 0.0000 0.04321(8) Uani 1 2 d S . . I1 I 0.22059(3) 0.511674(15) 0.48088(2) 0.03815(9) Uani 1 1 d . . . I2 I -0.28452(4) 0.595246(16) 0.21398(3) 0.04429(10) Uani 1 1 d . . . I3 I -0.00348(4) 0.310951(15) 0.45644(3) 0.04366(10) Uani 1 1 d . . . I4 I -0.15738(4) 0.401616(19) 0.12413(3) 0.05238(11) Uani 1 1 d . . . I5 I -0.58582(4) 0.41508(2) 0.15518(3) 0.06293(12) Uani 1 1 d . . . N11 N 0.4665(5) 0.70131(19) 0.4846(4) 0.0574(15) Uani 1 1 d . . . N12 N 0.3160(4) 0.6586(2) 0.2827(3) 0.0500(12) Uani 1 1 d . . . C11 C 0.7299(9) 0.7181(4) 0.6883(5) 0.107(3) Uani 1 1 d . . . H11A H 0.7609 0.7329 0.7597 0.161 Uiso 1 1 calc R . . H11B H 0.7897 0.7449 0.6668 0.161 Uiso 1 1 calc R . . H11C H 0.7653 0.6729 0.6945 0.161 Uiso 1 1 calc R . . C12 C 0.5448(7) 0.7234(3) 0.6064(5) 0.085(3) Uani 1 1 d . . . H12A H 0.5118 0.7691 0.6035 0.102 Uiso 1 1 calc R . . H12B H 0.4875 0.6977 0.6319 0.102 Uiso 1 1 calc R . . C13 C 0.5028(6) 0.7480(3) 0.4231(5) 0.0711(19) Uani 1 1 d . . . H13A H 0.6296 0.7566 0.4670 0.085 Uiso 1 1 calc R . . H13B H 0.4425 0.7895 0.4115 0.085 Uiso 1 1 calc R . . C14 C 0.4370(6) 0.7181(3) 0.3094(4) 0.0678(18) Uani 1 1 d . . . H14A H 0.5379 0.7042 0.3112 0.081 Uiso 1 1 calc R . . H14B H 0.3715 0.7511 0.2507 0.081 Uiso 1 1 calc R . . C15 C 0.2695(5) 0.6976(3) 0.4209(4) 0.0589(17) Uani 1 1 d . . . H15A H 0.2254 0.7397 0.4258 0.071 Uiso 1 1 calc R . . H15B H 0.2406 0.6644 0.4550 0.071 Uiso 1 1 calc R . . C16 C 0.1788(5) 0.6806(3) 0.2991(4) 0.0500(16) Uani 1 1 d . . . H16A H 0.1156 0.7188 0.2524 0.060 Uiso 1 1 calc R . . H16B H 0.0932 0.6455 0.2768 0.060 Uiso 1 1 calc R . . C17 C 0.5367(6) 0.6339(2) 0.4853(4) 0.0523(16) Uani 1 1 d . . . H17A H 0.5279 0.6044 0.5335 0.063 Uiso 1 1 calc R . . H17B H 0.6611 0.6373 0.5153 0.063 Uiso 1 1 calc R . . C18 C 0.4306(6) 0.6062(2) 0.3667(4) 0.0485(15) Uani 1 1 d . . . H18A H 0.5113 0.5891 0.3515 0.058 Uiso 1 1 calc R . . H18B H 0.3567 0.5701 0.3599 0.058 Uiso 1 1 calc R . . C19 C 0.2297(7) 0.6345(3) 0.1630(4) 0.073(2) Uani 1 1 d . . . H19A H 0.1610 0.6703 0.1111 0.088 Uiso 1 1 calc R . . H19B H 0.3226 0.6232 0.1552 0.088 Uiso 1 1 calc R . . C110 C 0.1111(7) 0.5763(3) 0.1303(5) 0.086(3) Uani 1 1 d . . . H11D H 0.0618 0.5638 0.0542 0.129 Uiso 1 1 calc R . . H11E H 0.0165 0.5873 0.1356 0.129 Uiso 1 1 calc R . . H11F H 0.1785 0.5402 0.1800 0.129 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.03984(7) 0.03069(10) 0.03805(8) -0.00081(7) 0.02209(6) -0.00004(7) Pb2 0.04708(11) 0.03565(15) 0.03669(12) -0.00024(11) 0.01940(10) 0.00438(12) I1 0.04045(11) 0.02944(16) 0.04827(14) 0.00276(13) 0.02844(10) 0.00222(12) I2 0.04712(14) 0.03028(17) 0.04571(15) -0.00300(13) 0.02234(12) 0.00156(14) I3 0.04899(13) 0.03057(17) 0.05357(16) -0.00171(14) 0.03170(12) -0.00143(13) I4 0.05926(14) 0.0536(2) 0.05214(16) 0.00165(15) 0.03744(12) 0.01089(16) I5 0.04330(13) 0.0597(2) 0.0819(2) -0.01296(19) 0.03520(14) -0.00790(16) N11 0.0545(19) 0.023(2) 0.085(3) 0.005(2) 0.0363(19) 0.0057(18) N12 0.0487(15) 0.054(3) 0.067(2) 0.0334(19) 0.0451(14) 0.0225(18) C11 0.116(4) 0.090(6) 0.094(4) -0.018(4) 0.050(4) 0.019(4) C12 0.069(3) 0.052(4) 0.097(4) -0.026(3) 0.029(3) -0.003(3) C13 0.066(2) 0.032(3) 0.136(4) 0.017(3) 0.071(2) 0.007(2) C14 0.062(2) 0.059(4) 0.115(3) 0.048(3) 0.070(2) 0.020(2) C15 0.0520(19) 0.036(3) 0.106(3) 0.016(3) 0.056(2) 0.015(2) C16 0.0352(17) 0.053(3) 0.075(3) 0.012(3) 0.0401(17) 0.011(2) C17 0.049(2) 0.023(3) 0.086(3) 0.018(2) 0.041(2) 0.012(2) C18 0.062(2) 0.030(3) 0.067(3) 0.018(2) 0.0464(19) 0.017(2) C19 0.077(3) 0.087(5) 0.066(3) 0.032(3) 0.048(2) 0.033(3) C110 0.079(3) 0.093(5) 0.068(4) -0.015(4) 0.033(3) 0.014(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 Pb1 I3 3.1651(4) . ? Pb1 I1 3.2001(4) . ? Pb1 I5 3.2200(4) . ? Pb1 I4 3.2248(5) . ? Pb1 I1 3.2319(5) 3_566 ? Pb1 I2 3.3110(4) . ? Pb1 Pb2 4.0642(4) . ? Pb2 I2 3.1930(4) . ? Pb2 I2 3.1930(4) 3_465 ? Pb2 I4 3.2586(4) 3_465 ? Pb2 I4 3.2586(4) . ? Pb2 I5 3.3247(5) . ? Pb2 I5 3.3247(5) 3_465 ? Pb2 Pb1 4.0642(4) 3_465 ? I1 Pb1 3.2319(4) 3_566 ? N11 C13 1.485(7) . ? N11 C15 1.491(6) . ? N11 C17 1.514(6) . ? N11 C12 1.550(8) . ? N12 C18 1.495(5) . ? N12 C16 1.508(6) . ? N12 C19 1.523(7) . ? N12 C14 1.537(6) . ? C11 C12 1.407(8) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.528(8) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.502(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.516(7) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C110 1.490(8) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C110 H11D 0.9600 . ? C110 H11E 0.9600 . ? C110 H11F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I3 Pb1 I1 89.812(9) . . ? I3 Pb1 I5 103.291(11) . . ? I1 Pb1 I5 166.869(11) . . ? I3 Pb1 I4 91.989(11) . . ? I1 Pb1 I4 96.732(11) . . ? I5 Pb1 I4 83.841(12) . . ? I3 Pb1 I1 89.149(11) . 3_566 ? I1 Pb1 I1 89.080(11) . 3_566 ? I5 Pb1 I1 90.242(12) . 3_566 ? I4 Pb1 I1 174.079(9) . 3_566 ? I3 Pb1 I2 172.534(9) . . ? I1 Pb1 I2 82.834(9) . . ? I5 Pb1 I2 84.084(10) . . ? I4 Pb1 I2 87.614(11) . . ? I1 Pb1 I2 92.008(10) 3_566 . ? I3 Pb1 Pb2 134.069(8) . . ? I1 Pb1 Pb2 117.898(9) . . ? I5 Pb1 Pb2 52.778(9) . . ? I4 Pb1 Pb2 51.552(7) . . ? I1 Pb1 Pb2 124.394(8) 3_566 . ? I2 Pb1 Pb2 50.039(6) . . ? I2 Pb2 I2 180.000(9) . 3_465 ? I2 Pb2 I4 90.937(10) . 3_465 ? I2 Pb2 I4 89.063(10) 3_465 3_465 ? I2 Pb2 I4 89.063(10) . . ? I2 Pb2 I4 90.937(10) 3_465 . ? I4 Pb2 I4 180.000(11) 3_465 . ? I2 Pb2 I5 84.282(11) . . ? I2 Pb2 I5 95.718(11) 3_465 . ? I4 Pb2 I5 98.312(11) 3_465 . ? I4 Pb2 I5 81.688(10) . . ? I2 Pb2 I5 95.718(11) . 3_465 ? I2 Pb2 I5 84.282(11) 3_465 3_465 ? I4 Pb2 I5 81.688(10) 3_465 3_465 ? I4 Pb2 I5 98.312(10) . 3_465 ? I5 Pb2 I5 180.000(12) . 3_465 ? I2 Pb2 Pb1 52.638(8) . . ? I2 Pb2 Pb1 127.363(8) 3_465 . ? I4 Pb2 Pb1 129.190(8) 3_465 . ? I4 Pb2 Pb1 50.810(8) . . ? I5 Pb2 Pb1 50.463(7) . . ? I5 Pb2 Pb1 129.537(7) 3_465 . ? I2 Pb2 Pb1 127.363(8) . 3_465 ? I2 Pb2 Pb1 52.637(8) 3_465 3_465 ? I4 Pb2 Pb1 50.810(8) 3_465 3_465 ? I4 Pb2 Pb1 129.190(8) . 3_465 ? I5 Pb2 Pb1 129.537(7) . 3_465 ? I5 Pb2 Pb1 50.463(7) 3_465 3_465 ? Pb1 Pb2 Pb1 180.000(5) . 3_465 ? Pb1 I1 Pb1 90.920(11) . 3_566 ? Pb2 I2 Pb1 77.323(9) . . ? Pb1 I4 Pb2 77.637(10) . . ? Pb1 I5 Pb2 76.759(11) . . ? C13 N11 C15 107.1(4) . . ? C13 N11 C17 108.9(5) . . ? C15 N11 C17 109.0(4) . . ? C13 N11 C12 113.8(4) . . ? C15 N11 C12 107.4(5) . . ? C17 N11 C12 110.5(4) . . ? C18 N12 C16 109.6(4) . . ? C18 N12 C19 111.0(4) . . ? C16 N12 C19 111.6(3) . . ? C18 N12 C14 106.9(3) . . ? C16 N12 C14 107.1(4) . . ? C19 N12 C14 110.5(4) . . ? C12 C11 H11A 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C12 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C11 C12 N11 117.7(6) . . ? C11 C12 H12A 107.9 . . ? N11 C12 H12A 107.9 . . ? C11 C12 H12B 107.9 . . ? N11 C12 H12B 107.9 . . ? H12A C12 H12B 107.2 . . ? N11 C13 C14 109.3(4) . . ? N11 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? N11 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.3 . . ? C13 C14 N12 110.2(4) . . ? C13 C14 H14A 109.6 . . ? N12 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? N12 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? N11 C15 C16 111.9(5) . . ? N11 C15 H15A 109.2 . . ? C16 C15 H15A 109.2 . . ? N11 C15 H15B 109.2 . . ? C16 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C15 C16 N12 109.4(3) . . ? C15 C16 H16A 109.8 . . ? N12 C16 H16A 109.8 . . ? C15 C16 H16B 109.8 . . ? N12 C16 H16B 109.8 . . ? H16A C16 H16B 108.2 . . ? N11 C17 C18 110.1(4) . . ? N11 C17 H17A 109.6 . . ? C18 C17 H17A 109.6 . . ? N11 C17 H17B 109.6 . . ? C18 C17 H17B 109.6 . . ? H17A C17 H17B 108.2 . . ? N12 C18 C17 110.4(4) . . ? N12 C18 H18A 109.6 . . ? C17 C18 H18A 109.6 . . ? N12 C18 H18B 109.6 . . ? C17 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? C110 C19 N12 114.1(5) . . ? C110 C19 H19A 108.7 . . ? N12 C19 H19A 108.7 . . ? C110 C19 H19B 108.7 . . ? N12 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C110 H11D 109.5 . . ? C19 C110 H11E 109.5 . . ? H11D C110 H11E 109.5 . . ? C19 C110 H11F 109.5 . . ? H11D C110 H11F 109.5 . . ? H11E C110 H11F 109.5 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.993 _refine_diff_density_min -1.454 _refine_diff_density_rms 0.188 _database_code_depnum_ccdc_archive 'CCDC 957318' ####################################################################### # # 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_Compound3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H26 N2, 0.5(I10 Pb3)' _chemical_formula_sum 'C24 H52 I10 N4 Pb3' _chemical_formula_weight 2287.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.839(4) _cell_length_b 20.008(6) _cell_length_c 12.216(4) _cell_angle_alpha 90.00 _cell_angle_beta 110.346(3) _cell_angle_gamma 90.00 _cell_volume 2483.9(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7345 _cell_measurement_theta_min 2.0485 _cell_measurement_theta_max 27.6296 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.058 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 16.376 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5853 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku mercury' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18127 _diffrn_reflns_av_R_equivalents 0.0664 _diffrn_reflns_av_sigmaI/netI 0.0479 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4595 _reflns_number_gt 3616 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0768P)^2^+0.7989P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00074(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4595 _refine_ls_number_parameters 194 _refine_ls_number_restraints 102 _refine_ls_R_factor_all 0.0599 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1463 _refine_ls_wR_factor_gt 0.1383 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.003 _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 Pb1 Pb 0.47320(2) 0.544404(12) 1.16255(2) 0.05407(8) Uani 1 1 d . . . Pb2 Pb 0.5000 0.5000 1.5000 0.05671(11) Uani 1 2 d S . . I2 I 0.71869(5) 0.52207(2) 1.07785(4) 0.06202(14) Uani 1 1 d . . . I5 I 0.66537(5) 0.60487(2) 1.40659(4) 0.06628(15) Uani 1 1 d . A . I4 I 0.51515(6) 0.39729(2) 1.30546(5) 0.08779(19) Uani 1 1 d . A . I1A I 0.44612(12) 0.68296(5) 1.03536(9) 0.0766(4) Uani 0.50 1 d P A 1 I1B I 0.38669(12) 0.67895(5) 1.05277(10) 0.0766(4) Uani 0.50 1 d P A 2 I3A I 0.24123(11) 0.54525(6) 1.28643(12) 0.0879(3) Uani 0.50 1 d P A 1 I3B I 0.25469(11) 0.57675(6) 1.27737(12) 0.0879(3) Uani 0.50 1 d P A 2 N2 N 0.9140(6) 0.6884(3) 0.9533(5) 0.079(2) Uani 1 1 d DU . . N1 N 0.9842(7) 0.6523(4) 0.7834(6) 0.107(3) Uani 1 1 d DU . . C4 C 1.0586(11) 0.7138(6) 0.8482(8) 0.156(4) Uani 1 1 d U . . H4A H 1.0447 0.7509 0.7941 0.187 Uiso 1 1 calc R . . H4B H 1.1522 0.7042 0.8789 0.187 Uiso 1 1 calc R . . C10 C 0.8474(10) 0.7092(4) 1.0441(6) 0.132(4) Uani 1 1 d DU . . H10A H 0.8196 0.7555 1.0313 0.158 Uiso 1 1 calc R . . H10B H 0.7699 0.6819 1.0324 0.158 Uiso 1 1 calc R . . C8 C 0.9975(11) 0.6005(5) 0.8659(8) 0.128(3) Uani 1 1 d U . . H8A H 1.0897 0.5885 0.9001 0.154 Uiso 1 1 calc R . . H8B H 0.9499 0.5615 0.8257 0.154 Uiso 1 1 calc R . . C9 C 0.9485(10) 0.6188(4) 0.9600(8) 0.117(3) Uani 1 1 d U . . H9A H 0.8719 0.5919 0.9538 0.140 Uiso 1 1 calc R . . H9B H 1.0158 0.6096 1.0350 0.140 Uiso 1 1 calc R . . C5 C 1.0119(12) 0.7335(6) 0.9489(9) 0.166(4) Uani 1 1 d U . . H5A H 1.0854 0.7325 1.0221 0.200 Uiso 1 1 calc R . . H5B H 0.9766 0.7785 0.9368 0.200 Uiso 1 1 calc R . . C1 C 1.0841(9) 0.5921(7) 0.5277(8) 0.167(6) Uani 1 1 d DU . . H1A H 1.0556 0.5541 0.4773 0.250 Uiso 1 1 calc R . . H1B H 1.1785 0.5939 0.5573 0.250 Uiso 1 1 calc R . . H1C H 1.0500 0.6322 0.4845 0.250 Uiso 1 1 calc R . . C3 C 1.0526(12) 0.6461(5) 0.6929(8) 0.188(6) Uani 1 1 d DU . . H3A H 1.0228 0.6828 0.6381 0.226 Uiso 1 1 calc R . . H3B H 1.1463 0.6520 0.7332 0.226 Uiso 1 1 calc R . . C12 C 0.8672(10) 0.7170(7) 1.2501(9) 0.230(5) Uani 1 1 d DU . . H12A H 0.9259 0.7121 1.3292 0.346 Uiso 1 1 calc R . . H12B H 0.7943 0.6868 1.2359 0.346 Uiso 1 1 calc R . . H12C H 0.8352 0.7621 1.2373 0.346 Uiso 1 1 calc R . . C11 C 0.9404(11) 0.7009(5) 1.1669(7) 0.165(5) Uani 1 1 d DU . . H11A H 1.0149 0.7307 1.1814 0.199 Uiso 1 1 calc R . . H11B H 0.9730 0.6553 1.1792 0.199 Uiso 1 1 calc R . . C2 C 1.0342(12) 0.5863(6) 0.6280(9) 0.191(7) Uani 1 1 d DU . . H2A H 0.9413 0.5752 0.5981 0.229 Uiso 1 1 calc R . . H2B H 1.0803 0.5502 0.6790 0.229 Uiso 1 1 calc R . . C6 C 0.8485(11) 0.6714(6) 0.7388(9) 0.134(5) Uani 1 1 d U . . H6A H 0.7942 0.6322 0.7097 0.160 Uiso 1 1 calc R . . H6B H 0.8339 0.7023 0.6745 0.160 Uiso 1 1 calc R . . C7 C 0.8116(13) 0.7027(6) 0.8302(10) 0.151(4) Uani 1 1 d U . . H7A H 0.7262 0.6861 0.8265 0.182 Uiso 1 1 calc R . . H7B H 0.8043 0.7506 0.8173 0.182 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.06015(15) 0.05329(13) 0.04440(13) -0.00357(10) 0.01265(11) 0.00402(11) Pb2 0.0700(2) 0.05555(18) 0.04950(18) -0.00658(14) 0.02695(15) -0.00571(16) I2 0.0605(2) 0.0657(2) 0.0575(2) -0.0085(2) 0.0174(2) -0.0078(2) I5 0.0779(3) 0.0731(3) 0.0426(2) -0.00130(19) 0.0143(2) -0.0225(2) I4 0.1464(4) 0.0489(2) 0.0879(3) -0.0101(2) 0.0658(3) -0.0025(3) I1A 0.0930(8) 0.0515(3) 0.0676(4) 0.0088(3) 0.0055(5) -0.0003(4) I1B 0.0930(8) 0.0515(3) 0.0676(4) 0.0088(3) 0.0055(5) -0.0003(4) I3A 0.0657(3) 0.0911(8) 0.1211(5) 0.0008(5) 0.0506(3) 0.0085(4) I3B 0.0657(3) 0.0911(8) 0.1211(5) 0.0008(5) 0.0506(3) 0.0085(4) N2 0.100(4) 0.053(3) 0.072(4) 0.009(3) 0.013(3) -0.012(3) N1 0.128(5) 0.129(5) 0.071(4) 0.011(4) 0.043(4) -0.007(5) C4 0.177(7) 0.197(8) 0.092(6) 0.018(6) 0.043(6) -0.113(6) C10 0.220(9) 0.055(4) 0.129(7) 0.005(5) 0.072(7) -0.012(6) C8 0.199(7) 0.110(6) 0.112(5) 0.043(5) 0.100(5) 0.059(6) C9 0.189(6) 0.070(4) 0.137(6) 0.036(4) 0.115(5) 0.045(5) C5 0.204(7) 0.208(8) 0.091(6) -0.011(6) 0.055(6) -0.137(6) C1 0.119(7) 0.250(14) 0.163(9) 0.063(9) 0.091(6) 0.067(8) C3 0.271(12) 0.123(8) 0.157(10) -0.014(8) 0.058(10) 0.013(10) C12 0.363(9) 0.197(13) 0.263(8) 0.028(9) 0.274(6) -0.017(10) C11 0.302(11) 0.063(5) 0.179(9) -0.011(6) 0.144(8) -0.011(7) C2 0.178(11) 0.176(11) 0.187(11) -0.020(10) 0.024(11) 0.054(10) C6 0.156(9) 0.129(7) 0.079(6) -0.001(6) -0.006(7) 0.020(7) C7 0.151(6) 0.145(6) 0.141(6) -0.014(5) 0.030(4) 0.028(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 I1B 3.0083(12) . ? Pb1 I1A 3.1415(12) . ? Pb1 I2 3.2038(11) . ? Pb1 I3B 3.2101(17) . ? Pb1 I5 3.2205(9) . ? Pb1 I2 3.2360(9) 3_667 ? Pb1 I3A 3.3552(17) . ? Pb1 I4 3.3714(10) . ? Pb2 I4 3.1889(9) . ? Pb2 I4 3.1889(9) 3_668 ? Pb2 I5 3.2155(8) 3_668 ? Pb2 I5 3.2155(8) . ? Pb2 I3A 3.2256(13) 3_668 ? Pb2 I3A 3.2256(13) . ? I2 Pb1 3.2360(9) 3_667 ? N2 C5 1.408(13) . ? N2 C9 1.436(10) . ? N2 C7 1.554(11) . ? N2 C10 1.575(11) . ? N1 C8 1.416(12) . ? N1 C6 1.431(13) . ? N1 C4 1.533(13) . ? N1 C3 1.536(12) . ? C4 C5 1.536(17) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C10 C11 1.498(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C8 C9 1.470(15) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C1 C2 1.507(13) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C3 C2 1.410(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C12 C11 1.525(13) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C6 C7 1.452(17) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 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 I1B Pb1 I1A 13.78(4) . . ? I1B Pb1 I2 98.39(3) . . ? I1A Pb1 I2 84.76(3) . . ? I1B Pb1 I3B 81.46(4) . . ? I1A Pb1 I3B 94.70(4) . . ? I2 Pb1 I3B 172.29(2) . . ? I1B Pb1 I5 94.45(3) . . ? I1A Pb1 I5 92.61(3) . . ? I2 Pb1 I5 90.51(3) . . ? I3B Pb1 I5 81.82(3) . . ? I1B Pb1 I2 87.76(3) . 3_667 ? I1A Pb1 I2 89.64(3) . 3_667 ? I2 Pb1 I2 89.62(3) . 3_667 ? I3B Pb1 I2 98.07(3) . 3_667 ? I5 Pb1 I2 177.750(14) . 3_667 ? I1B Pb1 I3A 91.74(4) . . ? I1A Pb1 I3A 105.24(3) . . ? I2 Pb1 I3A 169.44(2) . . ? I3B Pb1 I3A 11.35(3) . . ? I5 Pb1 I3A 85.73(3) . . ? I2 Pb1 I3A 93.75(3) 3_667 . ? I1B Pb1 I4 167.72(3) . . ? I1A Pb1 I4 177.65(2) . . ? I2 Pb1 I4 93.888(19) . . ? I3B Pb1 I4 86.38(3) . . ? I5 Pb1 I4 85.48(2) . . ? I2 Pb1 I4 92.27(2) 3_667 . ? I3A Pb1 I4 76.00(3) . . ? I4 Pb2 I4 180.000(1) . 3_668 ? I4 Pb2 I5 91.34(2) . 3_668 ? I4 Pb2 I5 88.66(2) 3_668 3_668 ? I4 Pb2 I5 88.66(2) . . ? I4 Pb2 I5 91.34(2) 3_668 . ? I5 Pb2 I5 180.0 3_668 . ? I4 Pb2 I3A 99.57(3) . 3_668 ? I4 Pb2 I3A 80.43(3) 3_668 3_668 ? I5 Pb2 I3A 87.99(3) 3_668 3_668 ? I5 Pb2 I3A 92.01(3) . 3_668 ? I4 Pb2 I3A 80.43(3) . . ? I4 Pb2 I3A 99.57(3) 3_668 . ? I5 Pb2 I3A 92.01(3) 3_668 . ? I5 Pb2 I3A 87.99(3) . . ? I3A Pb2 I3A 180.0 3_668 . ? Pb1 I2 Pb1 90.38(3) . 3_667 ? Pb2 I5 Pb1 79.77(2) . . ? Pb2 I4 Pb1 77.92(3) . . ? Pb2 I3A Pb1 77.66(4) . . ? C5 N2 C9 116.0(8) . . ? C5 N2 C7 97.9(8) . . ? C9 N2 C7 108.5(7) . . ? C5 N2 C10 113.1(7) . . ? C9 N2 C10 113.0(7) . . ? C7 N2 C10 106.6(7) . . ? C8 N1 C6 107.6(9) . . ? C8 N1 C4 108.3(7) . . ? C6 N1 C4 105.6(9) . . ? C8 N1 C3 119.9(8) . . ? C6 N1 C3 115.9(7) . . ? C4 N1 C3 97.9(8) . . ? N1 C4 C5 111.0(9) . . ? N1 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N1 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C11 C10 N2 111.2(8) . . ? C11 C10 H10A 109.4 . . ? N2 C10 H10A 109.4 . . ? C11 C10 H10B 109.4 . . ? N2 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N1 C8 C9 113.6(8) . . ? N1 C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N1 C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? N2 C9 C8 110.8(8) . . ? N2 C9 H9A 109.5 . . ? C8 C9 H9A 109.5 . . ? N2 C9 H9B 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N2 C5 C4 109.2(9) . . ? N2 C5 H5A 109.8 . . ? C4 C5 H5A 109.8 . . ? N2 C5 H5B 109.8 . . ? C4 C5 H5B 109.8 . . ? H5A C5 H5B 108.3 . . ? 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 . . ? C2 C3 N1 117.6(10) . . ? C2 C3 H3A 107.9 . . ? N1 C3 H3A 107.9 . . ? C2 C3 H3B 107.9 . . ? N1 C3 H3B 107.9 . . ? H3A C3 H3B 107.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C10 C11 C12 108.6(9) . . ? C10 C11 H11A 110.0 . . ? C12 C11 H11A 110.0 . . ? C10 C11 H11B 110.0 . . ? C12 C11 H11B 110.0 . . ? H11A C11 H11B 108.4 . . ? C3 C2 C1 111.7(11) . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2B 109.3 . . ? C1 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? N1 C6 C7 110.1(8) . . ? N1 C6 H6A 109.6 . . ? C7 C6 H6A 109.6 . . ? N1 C6 H6B 109.6 . . ? C7 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? C6 C7 N2 111.7(10) . . ? C6 C7 H7A 109.3 . . ? N2 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? N2 C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.928 _refine_diff_density_min -2.394 _refine_diff_density_rms 0.219 _database_code_depnum_ccdc_archive 'CCDC 957319' ####################################################################### # # 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_Compound4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'H(H3O)C6 H14 N2, I6 Pb' _chemical_formula_sum 'C6 H18 I6 N2 O Pb' _chemical_formula_weight 1102.81 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M P6(3)mc _symmetry_space_group_name_hall 'p 6c -2c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-x, -y, z+1/2' 'y, -x+y, z+1/2' 'x-y, x, z+1/2' '-y, -x, z' '-x+y, y, z' 'x, x-y, z' 'y, x, z+1/2' 'x-y, -y, z+1/2' '-x, -x+y, z+1/2' _cell_length_a 10.1927(4) _cell_length_b 10.1927(4) _cell_length_c 14.8276(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1334.07(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3727 _cell_measurement_theta_min 3.5889 _cell_measurement_theta_max 27.4198 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.745 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 13.257 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5034 _exptl_absorpt_correction_T_max 0.5034 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8311 _diffrn_reflns_av_R_equivalents 0.0303 _diffrn_reflns_av_sigmaI/netI 0.0167 _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 -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.73 _diffrn_reflns_theta_max 25.48 _reflns_number_total 940 _reflns_number_gt 930 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^+6.3084P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.590(11) _refine_ls_number_reflns 940 _refine_ls_number_parameters 38 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0297 _refine_ls_R_factor_gt 0.0294 _refine_ls_wR_factor_ref 0.0792 _refine_ls_wR_factor_gt 0.0791 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.166 _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 Pb1 Pb 1.3333 0.6667 0.21016(5) 0.0346(2) Uani 1 6 d S . . I2 I 1.17405(6) 0.82595(6) 0.32425(8) 0.0628(3) Uani 1 2 d S . . I1 I 1.47239(5) 0.94477(10) 0.07529(7) 0.0591(3) Uani 1 2 d S . . N1 N 0.6667 0.3333 0.2214(11) 0.032(4) Uani 1 6 d S . . H1C H 0.6667 0.3333 0.1600 0.038 Uiso 1 6 calc SR . . N2 N 0.6667 0.3333 0.3880(12) 0.032(4) Uani 1 6 d S . . H2C H 0.6667 0.3333 0.4493 0.038 Uiso 1 6 calc SR . . C1 C 0.7467(7) 0.4933(14) 0.2536(9) 0.039(3) Uani 1 2 d S . . H1A H 0.6956 0.5456 0.2313 0.047 Uiso 0.50 1 calc PR . . H1B H 0.8499 0.5456 0.2313 0.047 Uiso 0.50 1 calc PR . . C2 C 0.7468(8) 0.4936(16) 0.3570(11) 0.080(6) Uani 1 2 d S . . H2A H 0.8500 0.5456 0.3794 0.096 Uiso 0.50 1 calc PR . . H2B H 0.6956 0.5456 0.3794 0.096 Uiso 0.50 1 calc PR . . O1W O 0.6667 0.3333 0.0352(13) 0.062(6) Uani 1 6 d S . . 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 Pb1 0.0366(3) 0.0366(3) 0.0306(3) 0.000 0.000 0.01828(13) I2 0.0570(5) 0.0570(5) 0.0750(7) -0.0111(3) 0.0111(3) 0.0291(5) I1 0.0881(6) 0.0364(5) 0.0354(4) -0.0015(4) -0.00074(19) 0.0182(2) N1 0.040(5) 0.040(5) 0.016(8) 0.000 0.000 0.020(3) N2 0.035(6) 0.035(6) 0.025(9) 0.000 0.000 0.018(3) C1 0.045(5) 0.027(6) 0.040(6) 0.003(5) 0.002(3) 0.014(3) C2 0.131(15) 0.027(7) 0.048(8) -0.008(6) -0.004(3) 0.013(4) O1W 0.075(9) 0.075(9) 0.037(10) 0.000 0.000 0.037(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 I1 3.1663(11) 2_755 ? Pb1 I1 3.1663(11) . ? Pb1 I1 3.1663(11) 3_775 ? Pb1 I2 3.2817(11) . ? Pb1 I2 3.2817(11) 3_775 ? Pb1 I2 3.2817(11) 2_755 ? N1 C1 1.491(13) 3_665 ? N1 C1 1.491(13) . ? N1 C1 1.491(13) 2_655 ? N1 H1C 0.9100 . ? N2 C2 1.487(15) 3_665 ? N2 C2 1.487(15) 2_655 ? N2 C2 1.487(16) . ? N2 H2C 0.9100 . ? C1 C2 1.532(19) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 H2A 0.9700 . ? C2 H2B 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 I1 Pb1 I1 84.36(3) 2_755 . ? I1 Pb1 I1 84.36(3) 2_755 3_775 ? I1 Pb1 I1 84.36(3) . 3_775 ? I1 Pb1 I2 89.62(2) 2_755 . ? I1 Pb1 I2 89.62(2) . . ? I1 Pb1 I2 171.87(3) 3_775 . ? I1 Pb1 I2 171.87(3) 2_755 3_775 ? I1 Pb1 I2 89.62(2) . 3_775 ? I1 Pb1 I2 89.62(2) 3_775 3_775 ? I2 Pb1 I2 95.82(3) . 3_775 ? I1 Pb1 I2 89.62(2) 2_755 2_755 ? I1 Pb1 I2 171.87(3) . 2_755 ? I1 Pb1 I2 89.62(2) 3_775 2_755 ? I2 Pb1 I2 95.82(3) . 2_755 ? I2 Pb1 I2 95.82(3) 3_775 2_755 ? C1 N1 C1 110.2(8) 3_665 . ? C1 N1 C1 110.2(8) 3_665 2_655 ? C1 N1 C1 110.2(8) . 2_655 ? C1 N1 H1C 108.7 3_665 . ? C1 N1 H1C 108.7 . . ? C1 N1 H1C 108.7 2_655 . ? C2 N2 C2 110.9(9) 3_665 2_655 ? C2 N2 C2 110.9(9) 3_665 . ? C2 N2 C2 110.9(8) 2_655 . ? C2 N2 H2C 108.0 3_665 . ? C2 N2 H2C 108.0 2_655 . ? C2 N2 H2C 108.0 . . ? N1 C1 C2 108.8(11) . . ? N1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? N1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? N2 C2 C1 107.9(12) . . ? N2 C2 H2A 110.1 . . ? C1 C2 H2A 110.1 . . ? N2 C2 H2B 110.1 . . ? C1 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 25.48 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.952 _refine_diff_density_min -1.131 _refine_diff_density_rms 0.137 _database_code_depnum_ccdc_archive 'CCDC 957320' ####################################################################### # # 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_Compound5 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety I24Pb7,2(C8H18N2),2(C4H9N),2(C6H14N2) _chemical_formula_sum 'C36 H82 I24 N10 Pb7' _chemical_formula_weight 5151.05 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2 _symmetry_space_group_name_hall 'P 2 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' '-x+1/2, y+1/2, -z' 'x+1/2, -y+1/2, -z' _cell_length_a 15.5866(6) _cell_length_b 32.6596(15) _cell_length_c 9.4273(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4799.0(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13310 _cell_measurement_theta_min 2.2488 _cell_measurement_theta_max 27.4855 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.565 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4428 _exptl_absorpt_coefficient_mu 19.983 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1085 _exptl_absorpt_correction_T_max 0.4349 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Mercury CCD' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32319 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0587 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -39 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.14 _diffrn_reflns_theta_max 25.50 _reflns_number_total 8896 _reflns_number_gt 8042 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0003P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.009(3) _chemical_absolute_configuration ad _refine_ls_number_reflns 8896 _refine_ls_number_parameters 348 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0277 _refine_ls_wR_factor_ref 0.0442 _refine_ls_wR_factor_gt 0.0425 _refine_ls_goodness_of_fit_ref 0.886 _refine_ls_restrained_S_all 0.886 _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 Pb1 Pb 0.5000 0.5000 0.55629(4) 0.04509(10) Uani 1 2 d S . . Pb2 Pb 0.717377(14) 0.593410(7) 1.05490(3) 0.03653(6) Uani 1 1 d . . . Pb3 Pb 0.976772(15) 0.623543(8) 1.05854(3) 0.04094(6) Uani 1 1 d . . . Pb4 Pb 0.792551(16) 0.720210(8) 1.02609(2) 0.04175(7) Uani 1 1 d . . . I1 I 0.35714(3) 0.572855(17) 0.54389(5) 0.06842(16) Uani 1 1 d . . . I2 I 0.60536(3) 0.549293(15) 0.32093(5) 0.05496(13) Uani 1 1 d . . . I3 I 0.61713(3) 0.540705(14) 0.80758(5) 0.04912(12) Uani 1 1 d . . . I4 I 0.58574(3) 0.667073(13) 1.01973(4) 0.04705(12) Uani 1 1 d . . . I5 I 0.81918(3) 0.635584(13) 0.80747(4) 0.04162(12) Uani 1 1 d . . . I6 I 0.81084(3) 0.647598(14) 1.29312(4) 0.04658(12) Uani 1 1 d . . . I7 I 0.88038(3) 0.531545(13) 1.08981(4) 0.04635(12) Uani 1 1 d . . . I8 I 1.09430(3) 0.608256(14) 0.80133(4) 0.04781(12) Uani 1 1 d . . . I9 I 1.10621(3) 0.621252(14) 1.29889(4) 0.04906(13) Uani 1 1 d . . . I10 I 0.99209(3) 0.720061(12) 1.04098(4) 0.04440(11) Uani 1 1 d . . . I11 I 0.76557(3) 0.788154(14) 1.24015(5) 0.04801(13) Uani 1 1 d . . . I12 I 0.79782(3) 0.776171(14) 0.76696(4) 0.04513(12) Uani 1 1 d . . . N11 N 0.4335(3) 0.31589(14) 0.5533(5) 0.0332(13) Uani 1 1 d . . . N12 N 0.4728(3) 0.24336(14) 0.4695(5) 0.0382(14) Uani 1 1 d . . . N21 N 0.0770(4) 0.48592(16) 0.5564(6) 0.0623(18) Uani 1 1 d . . . N31 N 1.1241(4) 0.07381(19) 0.8290(5) 0.069(2) Uani 1 1 d . . . H41A H 1.1001 0.0670 0.7443 0.083 Uiso 1 1 calc R . . N32 N 1.1900(4) 0.09197(19) 1.0603(6) 0.070(2) Uani 1 1 d . . . H42A H 1.2139 0.0986 1.1454 0.084 Uiso 1 1 calc R . . C11 C 0.4088(5) 0.3586(2) 0.6008(7) 0.064(2) Uani 1 1 d . . . H11A H 0.3551 0.3661 0.5584 0.097 Uiso 1 1 calc R . . H11B H 0.4524 0.3777 0.5720 0.097 Uiso 1 1 calc R . . H11C H 0.4033 0.3591 0.7023 0.097 Uiso 1 1 calc R . . C12 C 0.4418(5) 0.3143(2) 0.3957(6) 0.054(2) Uani 1 1 d . . . H12A H 0.4894 0.3315 0.3663 0.065 Uiso 1 1 calc R . . H12B H 0.3900 0.3251 0.3526 0.065 Uiso 1 1 calc R . . C13 C 0.4569(4) 0.2710(2) 0.3438(5) 0.0424(19) Uani 1 1 d . . . H13A H 0.4071 0.2614 0.2916 0.051 Uiso 1 1 calc R . . H13B H 0.5060 0.2703 0.2807 0.051 Uiso 1 1 calc R . . C14 C 0.5165(4) 0.3023(2) 0.6162(6) 0.049(2) Uani 1 1 d . . . H14A H 0.5105 0.3005 0.7184 0.058 Uiso 1 1 calc R . . H14B H 0.5603 0.3226 0.5958 0.058 Uiso 1 1 calc R . . C15 C 0.5453(3) 0.26053(19) 0.5577(6) 0.0438(18) Uani 1 1 d . . . H15A H 0.5963 0.2638 0.4998 0.053 Uiso 1 1 calc R . . H15B H 0.5586 0.2421 0.6352 0.053 Uiso 1 1 calc R . . C16 C 0.3668(4) 0.2852(2) 0.5971(7) 0.054(2) Uani 1 1 d . . . H16A H 0.3131 0.2916 0.5500 0.065 Uiso 1 1 calc R . . H16B H 0.3575 0.2873 0.6985 0.065 Uiso 1 1 calc R . . C17 C 0.3928(4) 0.24189(17) 0.5606(6) 0.0383(16) Uani 1 1 d . . . H17A H 0.3469 0.2283 0.5095 0.046 Uiso 1 1 calc R . . H17B H 0.4041 0.2266 0.6467 0.046 Uiso 1 1 calc R . . C18 C 0.4959(5) 0.2014(2) 0.4178(7) 0.067(2) Uani 1 1 d . . . H18A H 0.5467 0.2029 0.3604 0.101 Uiso 1 1 calc R . . H18B H 0.4495 0.1906 0.3623 0.101 Uiso 1 1 calc R . . H18C H 0.5063 0.1838 0.4975 0.101 Uiso 1 1 calc R . . C21 C 0.1697(5) 0.4699(2) 0.5547(11) 0.111(4) Uani 1 1 d . . . H21A H 0.1875 0.4655 0.4584 0.166 Uiso 1 1 calc R . . H21B H 0.1726 0.4445 0.6059 0.166 Uiso 1 1 calc R . . H21C H 0.2068 0.4896 0.5987 0.166 Uiso 1 1 calc R . . C22 C -0.0734(4) 0.47422(18) 0.4774(7) 0.052(2) Uani 1 1 d . . . H22A H -0.0877 0.4787 0.3784 0.062 Uiso 1 1 calc R . . H22B H -0.1148 0.4552 0.5170 0.062 Uiso 1 1 calc R . . C23 C 0.0183(4) 0.45589(19) 0.4891(6) 0.054(2) Uani 1 1 d . . . H23A H 0.0166 0.4310 0.5454 0.065 Uiso 1 1 calc R . . H23B H 0.0394 0.4489 0.3954 0.065 Uiso 1 1 calc R . . C24 C 0.0460(6) 0.4933(3) 0.7058(6) 0.106(4) Uani 1 1 d . . . H24A H 0.0519 0.4684 0.7608 0.127 Uiso 1 1 calc R . . H24B H 0.0811 0.5143 0.7501 0.127 Uiso 1 1 calc R . . C31 C 1.1472(6) 0.1162(2) 0.8296(7) 0.086(3) Uani 1 1 d . . . H31A H 1.0956 0.1328 0.8243 0.104 Uiso 1 1 calc R . . H31B H 1.1819 0.1222 0.7467 0.104 Uiso 1 1 calc R . . C32 C 1.1964(4) 0.12728(18) 0.9612(7) 0.054(2) Uani 1 1 d . . . H32A H 1.2560 0.1326 0.9379 0.065 Uiso 1 1 calc R . . H32B H 1.1723 0.1517 1.0044 0.065 Uiso 1 1 calc R . . C33 C 1.2079(5) 0.0487(2) 0.8529(7) 0.069(3) Uani 1 1 d . . . H33A H 1.1968 0.0198 0.8378 0.083 Uiso 1 1 calc R . . H33B H 1.2517 0.0574 0.7864 0.083 Uiso 1 1 calc R . . C34 C 1.2366(4) 0.0554(2) 0.9962(8) 0.078(3) Uani 1 1 d . . . H34A H 1.2979 0.0605 0.9966 0.093 Uiso 1 1 calc R . . H34B H 1.2255 0.0312 1.0529 0.093 Uiso 1 1 calc R . . C35 C 1.0646(4) 0.0628(2) 0.9478(7) 0.058(2) Uani 1 1 d . . . H35A H 1.0086 0.0749 0.9321 0.070 Uiso 1 1 calc R . . H35B H 1.0580 0.0333 0.9534 0.070 Uiso 1 1 calc R . . C36 C 1.1025(4) 0.0787(3) 1.0805(7) 0.082(3) Uani 1 1 d . . . H36A H 1.0684 0.1015 1.1143 0.099 Uiso 1 1 calc R . . H36B H 1.1010 0.0574 1.1523 0.099 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.0595(2) 0.0459(2) 0.02985(16) 0.000 0.000 -0.01757(18) Pb2 0.04064(11) 0.03110(12) 0.03785(12) -0.00015(11) 0.00065(12) -0.00588(11) Pb3 0.04335(12) 0.03271(12) 0.04675(13) 0.00140(12) -0.00238(13) -0.00181(11) Pb4 0.04828(12) 0.03618(13) 0.04080(13) -0.00002(12) -0.00039(12) -0.00378(12) I1 0.0931(3) 0.0763(4) 0.0358(2) -0.0002(3) -0.0054(3) 0.0097(3) I2 0.0596(3) 0.0580(3) 0.0473(2) 0.0112(2) 0.0074(2) -0.0121(3) I3 0.0548(2) 0.0441(3) 0.0485(2) -0.0097(2) -0.0048(2) -0.0112(2) I4 0.0609(2) 0.0439(2) 0.0364(2) -0.00193(19) -0.0014(2) 0.0167(2) I5 0.0456(2) 0.0422(2) 0.0370(2) 0.00205(19) 0.0014(2) -0.0074(2) I6 0.0536(2) 0.0495(3) 0.0366(2) -0.0036(2) -0.0011(2) -0.0086(2) I7 0.0511(2) 0.0363(2) 0.0516(3) 0.0014(2) -0.0008(2) 0.0036(2) I8 0.0497(2) 0.0464(3) 0.0473(2) -0.0062(2) -0.0061(2) 0.0039(2) I9 0.0500(2) 0.0486(3) 0.0486(2) 0.0094(2) -0.0039(2) -0.0007(2) I10 0.0549(2) 0.0349(2) 0.0434(2) 0.0024(2) -0.0011(2) -0.0099(2) I11 0.0481(2) 0.0492(3) 0.0467(2) -0.0032(2) 0.0033(2) 0.0045(2) I12 0.0491(2) 0.0433(2) 0.0430(2) 0.0011(2) -0.0045(2) 0.0001(2) N11 0.041(2) 0.032(3) 0.026(2) -0.001(2) -0.002(2) -0.003(2) N12 0.050(3) 0.033(3) 0.031(3) -0.002(2) -0.001(3) 0.002(3) N21 0.084(4) 0.050(3) 0.053(3) 0.018(3) -0.032(3) -0.031(3) N31 0.082(4) 0.091(5) 0.036(3) 0.004(3) -0.017(3) -0.023(4) N32 0.075(4) 0.083(5) 0.051(3) 0.004(4) -0.026(4) 0.009(4) C11 0.079(5) 0.035(4) 0.079(5) -0.001(4) 0.022(4) 0.002(4) C12 0.078(5) 0.055(5) 0.028(3) 0.000(3) 0.005(3) 0.011(4) C13 0.039(3) 0.068(5) 0.020(3) 0.008(3) 0.001(3) -0.003(3) C14 0.037(3) 0.055(4) 0.054(4) 0.004(3) -0.007(3) 0.000(4) C15 0.043(3) 0.058(4) 0.031(3) -0.002(3) -0.013(3) 0.003(3) C16 0.046(4) 0.066(5) 0.050(4) -0.002(4) 0.008(3) -0.012(4) C17 0.046(3) 0.033(3) 0.036(3) -0.006(3) 0.006(3) -0.002(3) C18 0.072(5) 0.058(5) 0.073(5) -0.015(4) 0.009(5) -0.008(4) C21 0.108(6) 0.055(5) 0.169(9) 0.044(6) -0.056(7) -0.023(5) C22 0.079(4) 0.032(3) 0.045(4) -0.023(3) 0.010(4) -0.015(3) C23 0.082(5) 0.043(4) 0.037(4) 0.000(3) -0.001(4) -0.011(4) C24 0.237(12) 0.040(4) 0.041(4) 0.019(4) -0.056(5) -0.055(6) C31 0.149(7) 0.060(5) 0.050(4) -0.012(4) 0.001(5) -0.058(5) C32 0.071(4) 0.031(3) 0.061(4) 0.012(4) -0.015(4) -0.009(4) C33 0.066(5) 0.065(5) 0.077(5) -0.013(4) -0.004(5) 0.017(5) C34 0.070(4) 0.059(5) 0.104(6) -0.030(4) -0.030(5) 0.040(4) C35 0.037(3) 0.081(5) 0.056(4) 0.012(4) 0.009(4) -0.013(4) C36 0.068(4) 0.128(7) 0.050(4) 0.018(5) -0.021(4) -0.043(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 I2 3.1956(5) 2_665 ? Pb1 I2 3.1956(5) . ? Pb1 I1 3.2609(6) 2_665 ? Pb1 I1 3.2609(6) . ? Pb1 I3 3.2730(5) . ? Pb1 I3 3.2730(5) 2_665 ? Pb2 I5 3.1395(5) . ? Pb2 I4 3.1792(5) . ? Pb2 I6 3.2090(5) . ? Pb2 I7 3.2627(5) . ? Pb2 I3 3.2925(5) . ? Pb2 I2 3.3785(5) 1_556 ? Pb3 I9 3.0348(5) . ? Pb3 I8 3.0797(5) . ? Pb3 I10 3.1656(5) . ? Pb3 I7 3.3722(5) . ? Pb4 I11 3.0287(5) . ? Pb4 I12 3.0520(5) . ? Pb4 I10 3.1133(5) . ? I2 Pb2 3.3785(5) 1_554 ? N11 C14 1.491(7) . ? N11 C12 1.493(7) . ? N11 C16 1.501(7) . ? N11 C11 1.515(8) . ? N12 C18 1.499(8) . ? N12 C13 1.509(7) . ? N12 C15 1.510(7) . ? N12 C17 1.515(7) . ? N21 C23 1.483(8) . ? N21 C22 1.501(8) 2_565 ? N21 C24 1.508(8) . ? N21 C21 1.537(10) . ? N31 C31 1.430(9) . ? N31 C35 1.498(8) . ? N31 C33 1.559(9) . ? N31 H41A 0.9100 . ? N32 C36 1.445(8) . ? N32 C32 1.488(8) . ? N32 C34 1.521(9) . ? N32 H42A 0.9100 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.517(9) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.539(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.512(9) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 N21 1.501(8) 2_565 ? C22 C23 1.553(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C24 1.500(18) 2_565 ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C31 C32 1.503(9) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C34 1.440(9) . ? C33 H33A 0.9700 . ? C33 H33B 0.9700 . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 C36 1.477(9) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9700 . ? C36 H36B 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 I2 Pb1 I2 92.050(19) 2_665 . ? I2 Pb1 I1 87.617(14) 2_665 2_665 ? I2 Pb1 I1 89.529(14) . 2_665 ? I2 Pb1 I1 89.529(14) 2_665 . ? I2 Pb1 I1 87.617(14) . . ? I1 Pb1 I1 175.89(2) 2_665 . ? I2 Pb1 I3 173.637(13) 2_665 . ? I2 Pb1 I3 90.646(12) . . ? I1 Pb1 I3 86.642(13) 2_665 . ? I1 Pb1 I3 96.343(13) . . ? I2 Pb1 I3 90.646(12) 2_665 2_665 ? I2 Pb1 I3 173.637(13) . 2_665 ? I1 Pb1 I3 96.343(13) 2_665 2_665 ? I1 Pb1 I3 86.642(13) . 2_665 ? I3 Pb1 I3 87.264(18) . 2_665 ? I5 Pb2 I4 85.220(13) . . ? I5 Pb2 I6 92.786(13) . . ? I4 Pb2 I6 87.054(13) . . ? I5 Pb2 I7 87.310(12) . . ? I4 Pb2 I7 169.009(14) . . ? I6 Pb2 I7 85.266(13) . . ? I5 Pb2 I3 86.734(13) . . ? I4 Pb2 I3 90.888(13) . . ? I6 Pb2 I3 177.919(14) . . ? I7 Pb2 I3 96.730(13) . . ? I5 Pb2 I2 179.040(15) . 1_556 ? I4 Pb2 I2 93.820(13) . 1_556 ? I6 Pb2 I2 87.151(13) . 1_556 ? I7 Pb2 I2 93.639(13) . 1_556 ? I3 Pb2 I2 93.295(13) . 1_556 ? I9 Pb3 I8 100.862(14) . . ? I9 Pb3 I10 90.771(13) . . ? I8 Pb3 I10 94.324(13) . . ? I9 Pb3 I7 102.062(13) . . ? I8 Pb3 I7 100.917(13) . . ? I10 Pb3 I7 157.728(13) . . ? I11 Pb4 I12 95.642(14) . . ? I11 Pb4 I10 96.305(13) . . ? I12 Pb4 I10 90.582(13) . . ? Pb1 I2 Pb2 174.782(18) . 1_554 ? Pb1 I3 Pb2 171.735(17) . . ? Pb2 I7 Pb3 77.665(11) . . ? Pb4 I10 Pb3 85.904(12) . . ? C14 N11 C12 108.1(5) . . ? C14 N11 C16 107.1(4) . . ? C12 N11 C16 108.2(5) . . ? C14 N11 C11 112.1(5) . . ? C12 N11 C11 110.4(5) . . ? C16 N11 C11 111.0(5) . . ? C18 N12 C13 109.3(5) . . ? C18 N12 C15 109.8(5) . . ? C13 N12 C15 109.5(4) . . ? C18 N12 C17 110.7(5) . . ? C13 N12 C17 109.2(4) . . ? C15 N12 C17 108.4(4) . . ? C23 N21 C22 109.7(5) . 2_565 ? C23 N21 C24 107.9(5) . . ? C22 N21 C24 108.2(5) 2_565 . ? C23 N21 C21 110.5(5) . . ? C22 N21 C21 109.0(5) 2_565 . ? C24 N21 C21 111.4(6) . . ? C31 N31 C35 112.7(6) . . ? C31 N31 C33 107.4(6) . . ? C35 N31 C33 106.5(5) . . ? C31 N31 H41A 110.1 . . ? C35 N31 H41A 110.1 . . ? C33 N31 H41A 110.1 . . ? C36 N32 C32 112.3(6) . . ? C36 N32 C34 105.5(6) . . ? C32 N32 C34 109.0(5) . . ? C36 N32 H42A 110.0 . . ? C32 N32 H42A 110.0 . . ? C34 N32 H42A 110.0 . . ? N11 C11 H11A 109.5 . . ? N11 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N11 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N11 C12 C13 111.5(5) . . ? N11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? N11 C12 H12B 109.3 . . ? C13 C12 H12B 109.3 . . ? H12A C12 H12B 108.0 . . ? N12 C13 C12 109.3(4) . . ? N12 C13 H13A 109.8 . . ? C12 C13 H13A 109.8 . . ? N12 C13 H13B 109.8 . . ? C12 C13 H13B 109.8 . . ? H13A C13 H13B 108.3 . . ? N11 C14 C15 112.0(5) . . ? N11 C14 H14A 109.2 . . ? C15 C14 H14A 109.2 . . ? N11 C14 H14B 109.2 . . ? C15 C14 H14B 109.2 . . ? H14A C14 H14B 107.9 . . ? N12 C15 C14 108.0(4) . . ? N12 C15 H15A 110.1 . . ? C14 C15 H15A 110.1 . . ? N12 C15 H15B 110.1 . . ? C14 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? N11 C16 C17 112.1(5) . . ? N11 C16 H16A 109.2 . . ? C17 C16 H16A 109.2 . . ? N11 C16 H16B 109.2 . . ? C17 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C16 C17 N12 108.7(4) . . ? C16 C17 H17A 110.0 . . ? N12 C17 H17A 110.0 . . ? C16 C17 H17B 110.0 . . ? N12 C17 H17B 110.0 . . ? H17A C17 H17B 108.3 . . ? N12 C18 H18A 109.5 . . ? N12 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N12 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N21 C21 H21A 109.5 . . ? N21 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? N21 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N21 C22 C23 109.5(5) 2_565 . ? N21 C22 H22A 109.8 2_565 . ? C23 C22 H22A 109.8 . . ? N21 C22 H22B 109.8 2_565 . ? C23 C22 H22B 109.8 . . ? H22A C22 H22B 108.2 . . ? N21 C23 C22 110.1(5) . . ? N21 C23 H23A 109.6 . . ? C22 C23 H23A 109.6 . . ? N21 C23 H23B 109.6 . . ? C22 C23 H23B 109.6 . . ? H23A C23 H23B 108.2 . . ? C24 C24 N21 110.7(4) 2_565 . ? C24 C24 H24A 109.5 2_565 . ? N21 C24 H24A 109.5 . . ? C24 C24 H24B 109.5 2_565 . ? N21 C24 H24B 109.5 . . ? H24A C24 H24B 108.1 . . ? N31 C31 C32 111.4(6) . . ? N31 C31 H31A 109.4 . . ? C32 C31 H31A 109.4 . . ? N31 C31 H31B 109.4 . . ? C32 C31 H31B 109.4 . . ? H31A C31 H31B 108.0 . . ? N32 C32 C31 107.3(5) . . ? N32 C32 H32A 110.3 . . ? C31 C32 H32A 110.3 . . ? N32 C32 H32B 110.3 . . ? C31 C32 H32B 110.3 . . ? H32A C32 H32B 108.5 . . ? C34 C33 N31 108.4(6) . . ? C34 C33 H33A 110.0 . . ? N31 C33 H33A 110.0 . . ? C34 C33 H33B 110.0 . . ? N31 C33 H33B 110.0 . . ? H33A C33 H33B 108.4 . . ? C33 C34 N32 110.2(6) . . ? C33 C34 H34A 109.6 . . ? N32 C34 H34A 109.6 . . ? C33 C34 H34B 109.6 . . ? N32 C34 H34B 109.6 . . ? H34A C34 H34B 108.1 . . ? C36 C35 N31 107.6(5) . . ? C36 C35 H35A 110.2 . . ? N31 C35 H35A 110.2 . . ? C36 C35 H35B 110.2 . . ? N31 C35 H35B 110.2 . . ? H35A C35 H35B 108.5 . . ? N32 C36 C35 111.8(6) . . ? N32 C36 H36A 109.3 . . ? C35 C36 H36A 109.3 . . ? N32 C36 H36B 109.3 . . ? C35 C36 H36B 109.3 . . ? H36A C36 H36B 107.9 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.745 _refine_diff_density_min -0.928 _refine_diff_density_rms 0.153 _database_code_depnum_ccdc_archive 'CCDC 957321' ####################################################################### # # 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_Compound6 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H26 N2, I6 Pb2, 0.5(H2 O)' _chemical_formula_sum 'C40 H54 I12 N4 O Pb4' _chemical_formula_weight 2958.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.3944 10.1111 '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 _symmetry_space_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.1225(11) _cell_length_b 22.378(3) _cell_length_c 15.398(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.343(2) _cell_angle_gamma 90.00 _cell_volume 3129.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9645 _cell_measurement_theta_min 2.2423 _cell_measurement_theta_max 27.4932 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2588 _exptl_absorpt_coefficient_mu 16.676 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.1352 _exptl_absorpt_correction_T_max 0.2864 _exptl_absorpt_process_details 'Sphere (Rigaku CrystalClear)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku MM007-Saturn 724+' _diffrn_measurement_method CCD_Profile_fitting _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23249 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.50 _reflns_number_total 5775 _reflns_number_gt 4863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'Siemens SHELXTL^TM^ 5' _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^)+(0.0174P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5775 _refine_ls_number_parameters 286 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0219 _refine_ls_wR_factor_ref 0.0448 _refine_ls_wR_factor_gt 0.0439 _refine_ls_goodness_of_fit_ref 0.951 _refine_ls_restrained_S_all 0.951 _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 Pb1 Pb 0.44831(2) 0.074169(9) 0.600508(12) 0.03428(6) Uani 1 1 d . . . Pb2 Pb 0.01635(2) 0.097925(9) 0.461477(13) 0.03939(6) Uani 1 1 d . . . I1 I 0.52642(4) 0.107438(18) 0.79122(2) 0.04832(10) Uani 1 1 d . . . I2 I 0.71059(4) 0.150773(18) 0.52443(2) 0.04702(10) Uani 1 1 d . . . I3 I 0.15197(4) 0.006288(16) 0.65335(2) 0.04671(10) Uani 1 1 d . . . I4 I 0.31628(4) 0.040600(16) 0.39467(2) 0.04259(9) Uani 1 1 d . . . I5 I 0.23669(4) 0.186772(15) 0.58053(2) 0.03764(9) Uani 1 1 d . . . I6 I -0.00852(4) 0.188208(18) 0.31914(3) 0.05034(11) Uani 1 1 d . . . N1 N 0.4529(4) 0.24688(17) 0.2981(3) 0.0327(9) Uani 1 1 d . . . N2 N 0.5037(4) 0.35345(19) 0.3559(3) 0.0378(10) Uani 1 1 d . . . C1 C 0.6119(6) 0.1250(2) 0.2059(4) 0.0474(14) Uani 1 1 d . . . H1A H 0.6453 0.1142 0.2626 0.057 Uiso 1 1 calc R . . C2 C 0.6809(7) 0.1024(3) 0.1366(4) 0.0606(17) Uani 1 1 d . . . H2A H 0.7590 0.0758 0.1467 0.073 Uiso 1 1 calc R . . C3 C 0.6333(7) 0.1193(3) 0.0525(4) 0.0636(18) Uani 1 1 d . . . H3A H 0.6796 0.1042 0.0059 0.076 Uiso 1 1 calc R . . C4 C 0.5167(7) 0.1589(3) 0.0374(4) 0.0550(16) Uani 1 1 d . . . H4A H 0.4865 0.1714 -0.0190 0.066 Uiso 1 1 calc R . . C5 C 0.4462(6) 0.1793(2) 0.1068(4) 0.0488(15) Uani 1 1 d . . . H5A H 0.3649 0.2043 0.0967 0.059 Uiso 1 1 calc R . . C6 C 0.4945(5) 0.1633(2) 0.1914(4) 0.0397(13) Uani 1 1 d . . . C7 C 0.4178(6) 0.1833(2) 0.2683(4) 0.0465(14) Uani 1 1 d . . . H7A H 0.4443 0.1564 0.3166 0.056 Uiso 1 1 calc R . . H7B H 0.3124 0.1800 0.2536 0.056 Uiso 1 1 calc R . . C8 C 0.6160(4) 0.2584(2) 0.3137(3) 0.0352(12) Uani 1 1 d . . . H8A H 0.6587 0.2596 0.2583 0.042 Uiso 1 1 calc R . . H8B H 0.6626 0.2262 0.3483 0.042 Uiso 1 1 calc R . . C9 C 0.6444(5) 0.3177(2) 0.3613(4) 0.0413(13) Uani 1 1 d . . . H9A H 0.6786 0.3104 0.4219 0.050 Uiso 1 1 calc R . . H9B H 0.7200 0.3399 0.3348 0.050 Uiso 1 1 calc R . . C10 C 0.3881(6) 0.2918(2) 0.2347(3) 0.0422(13) Uani 1 1 d . . . H10A H 0.2815 0.2903 0.2324 0.051 Uiso 1 1 calc R . . H10B H 0.4164 0.2827 0.1770 0.051 Uiso 1 1 calc R . . C11 C 0.4408(6) 0.3541(2) 0.2610(3) 0.0447(14) Uani 1 1 d . . . H11A H 0.3593 0.3820 0.2534 0.054 Uiso 1 1 calc R . . H11B H 0.5157 0.3669 0.2243 0.054 Uiso 1 1 calc R . . C12 C 0.3911(5) 0.2558(3) 0.3839(3) 0.0447(14) Uani 1 1 d . . . H12A H 0.4470 0.2324 0.4285 0.054 Uiso 1 1 calc R . . H12B H 0.2897 0.2422 0.3798 0.054 Uiso 1 1 calc R . . C13 C 0.3982(5) 0.3210(3) 0.4084(3) 0.0444(14) Uani 1 1 d . . . H13A H 0.3010 0.3386 0.3980 0.053 Uiso 1 1 calc R . . H13B H 0.4300 0.3249 0.4701 0.053 Uiso 1 1 calc RD . . C14 C 0.5249(6) 0.4179(2) 0.3837(4) 0.0534(16) Uani 1 1 d . . . H14A H 0.5761 0.4384 0.3399 0.064 Uiso 1 1 calc R . . H14B H 0.4285 0.4362 0.3837 0.064 Uiso 1 1 calc R . . C15 C 0.6076(6) 0.4291(2) 0.4710(4) 0.0429(13) Uani 1 1 d . . . C16 C 0.7492(6) 0.4517(2) 0.4756(4) 0.0528(15) Uani 1 1 d . . . H16A H 0.7964 0.4567 0.4251 0.063 Uiso 1 1 calc R . . C17 C 0.8205(6) 0.4670(3) 0.5563(5) 0.0611(17) Uani 1 1 d . . . H17A H 0.9150 0.4828 0.5589 0.073 Uiso 1 1 calc R . . C18 C 0.7562(7) 0.4594(3) 0.6307(4) 0.0581(17) Uani 1 1 d . . . H18A H 0.8062 0.4697 0.6840 0.070 Uiso 1 1 calc R . . C19 C 0.6180(8) 0.4368(3) 0.6273(4) 0.069(2) Uani 1 1 d . . . H19A H 0.5741 0.4305 0.6787 0.083 Uiso 1 1 calc R . . C20 C 0.5419(7) 0.4228(3) 0.5483(4) 0.068(2) Uani 1 1 d . . . H20A H 0.4454 0.4091 0.5467 0.082 Uiso 1 1 calc R . . O1W O 0.5703(10) 0.2854(4) 0.5971(6) 0.072(3) Uani 0.50 1 d PD . . H1WA H 0.489(6) 0.304(5) 0.5876(19) 0.107 Uiso 0.50 1 d PD . . H1WB H 0.634(9) 0.314(4) 0.599(10) 0.107 Uiso 0.50 1 d PD . . 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 Pb1 0.03397(11) 0.04170(12) 0.02686(11) -0.00187(9) 0.00122(8) 0.00237(8) Pb2 0.03874(12) 0.04244(12) 0.03656(12) -0.00210(10) 0.00113(9) 0.00114(9) I1 0.0442(2) 0.0711(3) 0.02876(19) -0.00911(18) -0.00121(15) -0.00093(18) I2 0.0372(2) 0.0642(2) 0.0408(2) 0.00571(19) 0.00963(16) -0.00183(17) I3 0.0512(2) 0.0444(2) 0.0455(2) -0.00403(18) 0.00978(17) -0.01390(17) I4 0.0491(2) 0.0470(2) 0.03150(19) -0.00204(16) 0.00264(15) 0.01399(16) I5 0.0427(2) 0.03807(19) 0.03270(19) -0.00272(15) 0.00654(15) 0.00509(14) I6 0.03472(19) 0.0616(2) 0.0544(2) 0.0150(2) 0.00289(17) 0.00171(16) N1 0.029(2) 0.041(2) 0.029(2) 0.0086(19) 0.0083(17) -0.0008(18) N2 0.036(2) 0.046(3) 0.031(2) 0.003(2) 0.0013(19) 0.0047(19) C1 0.045(3) 0.055(4) 0.043(3) -0.006(3) 0.008(3) 0.001(3) C2 0.062(4) 0.066(4) 0.054(4) -0.008(4) 0.009(3) 0.013(3) C3 0.067(4) 0.071(5) 0.056(4) -0.020(4) 0.021(3) -0.017(4) C4 0.072(4) 0.055(4) 0.038(4) 0.000(3) 0.006(3) -0.011(3) C5 0.056(4) 0.046(3) 0.043(4) -0.008(3) -0.006(3) -0.003(3) C6 0.038(3) 0.039(3) 0.042(3) -0.002(3) 0.005(2) -0.008(2) C7 0.043(3) 0.047(3) 0.049(4) 0.004(3) 0.005(3) -0.008(3) C8 0.022(2) 0.045(3) 0.039(3) 0.007(2) 0.007(2) 0.004(2) C9 0.031(3) 0.046(3) 0.046(3) 0.002(3) 0.001(2) -0.002(2) C10 0.047(3) 0.053(3) 0.026(3) 0.006(3) -0.004(2) 0.013(3) C11 0.060(3) 0.045(3) 0.028(3) 0.006(3) 0.001(3) 0.011(3) C12 0.037(3) 0.068(4) 0.032(3) 0.002(3) 0.016(2) -0.010(3) C13 0.039(3) 0.068(4) 0.027(3) 0.002(3) 0.008(2) 0.006(3) C14 0.070(4) 0.045(3) 0.044(4) -0.005(3) 0.002(3) 0.012(3) C15 0.050(3) 0.041(3) 0.038(3) -0.006(3) 0.003(3) 0.003(3) C16 0.056(4) 0.046(3) 0.058(4) -0.003(3) 0.020(3) 0.002(3) C17 0.044(3) 0.064(4) 0.073(5) -0.007(4) -0.004(3) -0.001(3) C18 0.082(5) 0.052(4) 0.038(4) -0.004(3) -0.005(3) 0.003(3) C19 0.106(6) 0.065(5) 0.039(4) -0.006(3) 0.022(4) -0.024(4) C20 0.064(4) 0.087(5) 0.057(4) -0.026(4) 0.024(3) -0.024(4) O1W 0.064(5) 0.075(6) 0.074(7) -0.014(5) 0.001(5) -0.011(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 I1 3.0489(5) . ? Pb1 I5 3.1719(5) . ? Pb1 I2 3.2493(5) . ? Pb1 I3 3.2692(5) . ? Pb1 I4 3.3443(5) 3_656 ? Pb1 I4 3.3690(5) . ? Pb2 I6 2.9739(5) . ? Pb2 I3 3.2276(5) 3_556 ? Pb2 I2 3.2592(5) 1_455 ? Pb2 I5 3.2662(4) . ? Pb2 I4 3.2733(5) . ? I2 Pb2 3.2592(5) 1_655 ? I3 Pb2 3.2276(5) 3_556 ? I4 Pb1 3.3443(5) 3_656 ? N1 C10 1.486(6) . ? N1 C12 1.497(6) . ? N1 C8 1.507(5) . ? N1 C7 1.520(6) . ? N2 C13 1.502(6) . ? N2 C9 1.507(6) . ? N2 C14 1.513(6) . ? N2 C11 1.519(6) . ? C1 C6 1.373(7) . ? C1 C2 1.384(8) . ? C1 H1A 0.9300 . ? C2 C3 1.380(8) . ? C2 H2A 0.9300 . ? C3 C4 1.386(8) . ? C3 H3A 0.9300 . ? C4 C5 1.377(8) . ? C4 H4A 0.9300 . ? C5 C6 1.383(7) . ? C5 H5A 0.9300 . ? C6 C7 1.498(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.526(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.516(7) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.506(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.500(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.383(7) . ? C15 C20 1.389(8) . ? C16 C17 1.391(8) . ? C16 H16A 0.9300 . ? C17 C18 1.345(8) . ? C17 H17A 0.9300 . ? C18 C19 1.356(8) . ? C18 H18A 0.9300 . ? C19 C20 1.380(8) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? O1W H1WA 0.86(2) . ? O1W H1WB 0.86(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I1 Pb1 I5 89.139(11) . . ? I1 Pb1 I2 95.999(12) . . ? I5 Pb1 I2 90.449(13) . . ? I1 Pb1 I3 89.899(12) . . ? I5 Pb1 I3 83.303(13) . . ? I2 Pb1 I3 171.352(11) . . ? I1 Pb1 I4 94.251(11) . 3_656 ? I5 Pb1 I4 174.910(11) . 3_656 ? I2 Pb1 I4 85.428(13) . 3_656 ? I3 Pb1 I4 100.475(14) . 3_656 ? I1 Pb1 I4 172.570(11) . . ? I5 Pb1 I4 85.690(10) . . ? I2 Pb1 I4 89.381(12) . . ? I3 Pb1 I4 84.209(12) . . ? I4 Pb1 I4 91.274(10) 3_656 . ? I6 Pb2 I3 95.014(15) . 3_556 ? I6 Pb2 I2 87.937(12) . 1_455 ? I3 Pb2 I2 92.779(13) 3_556 1_455 ? I6 Pb2 I5 90.044(14) . . ? I3 Pb2 I5 169.689(11) 3_556 . ? I2 Pb2 I5 96.384(13) 1_455 . ? I6 Pb2 I4 92.480(12) . . ? I3 Pb2 I4 85.042(13) 3_556 . ? I2 Pb2 I4 177.808(11) 1_455 . ? I5 Pb2 I4 85.769(12) . . ? Pb1 I2 Pb2 126.521(15) . 1_655 ? Pb2 I3 Pb1 124.168(14) 3_556 . ? Pb2 I4 Pb1 147.977(13) . 3_656 ? Pb2 I4 Pb1 81.547(11) . . ? Pb1 I4 Pb1 88.726(10) 3_656 . ? Pb1 I5 Pb2 84.722(12) . . ? C10 N1 C12 109.3(4) . . ? C10 N1 C8 108.4(4) . . ? C12 N1 C8 106.5(4) . . ? C10 N1 C7 112.0(4) . . ? C12 N1 C7 107.8(4) . . ? C8 N1 C7 112.7(4) . . ? C13 N2 C9 107.4(4) . . ? C13 N2 C14 112.4(4) . . ? C9 N2 C14 113.9(4) . . ? C13 N2 C11 108.6(4) . . ? C9 N2 C11 107.6(4) . . ? C14 N2 C11 106.9(4) . . ? C6 C1 C2 120.4(6) . . ? C6 C1 H1A 119.8 . . ? C2 C1 H1A 119.8 . . ? C3 C2 C1 119.8(6) . . ? C3 C2 H2A 120.1 . . ? C1 C2 H2A 120.1 . . ? C2 C3 C4 120.2(6) . . ? C2 C3 H3A 119.9 . . ? C4 C3 H3A 119.9 . . ? C5 C4 C3 119.2(6) . . ? C5 C4 H4A 120.4 . . ? C3 C4 H4A 120.4 . . ? C4 C5 C6 120.9(6) . . ? C4 C5 H5A 119.5 . . ? C6 C5 H5A 119.5 . . ? C1 C6 C5 119.4(5) . . ? C1 C6 C7 118.2(5) . . ? C5 C6 C7 122.3(5) . . ? C6 C7 N1 114.7(4) . . ? C6 C7 H7A 108.6 . . ? N1 C7 H7A 108.6 . . ? C6 C7 H7B 108.6 . . ? N1 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? N1 C8 C9 110.3(4) . . ? N1 C8 H8A 109.6 . . ? C9 C8 H8A 109.6 . . ? N1 C8 H8B 109.6 . . ? C9 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? N2 C9 C8 109.2(4) . . ? N2 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? N2 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.3 . . ? N1 C10 C11 110.4(4) . . ? N1 C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? N1 C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C10 C11 N2 109.3(4) . . ? C10 C11 H11A 109.8 . . ? N2 C11 H11A 109.8 . . ? C10 C11 H11B 109.8 . . ? N2 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? N1 C12 C13 109.9(4) . . ? N1 C12 H12A 109.7 . . ? C13 C12 H12A 109.7 . . ? N1 C12 H12B 109.7 . . ? C13 C12 H12B 109.7 . . ? H12A C12 H12B 108.2 . . ? N2 C13 C12 110.3(4) . . ? N2 C13 H13A 109.6 . . ? C12 C13 H13A 109.6 . . ? N2 C13 H13B 109.6 . . ? C12 C13 H13B 109.6 . . ? H13A C13 H13B 108.1 . . ? C15 C14 N2 116.9(4) . . ? C15 C14 H14A 108.1 . . ? N2 C14 H14A 108.1 . . ? C15 C14 H14B 108.1 . . ? N2 C14 H14B 108.1 . . ? H14A C14 H14B 107.3 . . ? C16 C15 C20 118.0(5) . . ? C16 C15 C14 119.7(5) . . ? C20 C15 C14 122.0(5) . . ? C15 C16 C17 119.5(6) . . ? C15 C16 H16A 120.3 . . ? C17 C16 H16A 120.3 . . ? C18 C17 C16 121.8(6) . . ? C18 C17 H17A 119.1 . . ? C16 C17 H17A 119.1 . . ? C17 C18 C19 119.4(6) . . ? C17 C18 H18A 120.3 . . ? C19 C18 H18A 120.3 . . ? C18 C19 C20 120.5(6) . . ? C18 C19 H19A 119.7 . . ? C20 C19 H19A 119.7 . . ? C19 C20 C15 120.8(6) . . ? C19 C20 H20A 119.6 . . ? C15 C20 H20A 119.6 . . ? H1WA O1W H1WB 102(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.023 _refine_diff_density_min -0.786 _refine_diff_density_rms 0.128 _database_code_depnum_ccdc_archive 'CCDC 957322'