# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr XiaoMing Ren' _publ_contact_author_email xmren@njut.edu.cn _publ_section_title ; Inorganic-organic hybrid compounds based on face-sharing octahedral [PbI3][?] chains: self-assemblies, crystal structures, and ferroelectric, photoluminescence properties ; _publ_author_name 'XiaoMing Ren' #================= data_ben-780403 _database_code_depnum_ccdc_archive 'CCDC 780403' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H11 I3 N2 Pb' _chemical_formula_weight 771.12 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 'P 21/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 10.1409(19) _cell_length_b 22.136(4) _cell_length_c 8.0822(15) _cell_angle_alpha 90.00 _cell_angle_beta 100.913(2) _cell_angle_gamma 90.00 _cell_volume 1781.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4323 _cell_measurement_theta_min 2.2427 _cell_measurement_theta_max 26.3836 _exptl_crystal_description neddle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.875 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1352 _exptl_absorpt_coefficient_mu 14.656 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5277 _exptl_absorpt_correction_T_max 0.8673 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15604 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 27.70 _reflns_number_total 4156 _reflns_number_gt 3089 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0122P)^2^+1.1697P] 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 4156 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0511 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0617 _refine_ls_wR_factor_gt 0.0557 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 0.21920(2) 0.252425(10) 0.72701(3) 0.04373(8) Uani 1 1 d . . . I1 I 0.21353(4) 0.367031(18) 0.94610(6) 0.05236(12) Uani 1 1 d . . . I2 I 0.45264(4) 0.294770(19) 0.53886(6) 0.05447(12) Uani 1 1 d . . . I3 I -0.00065(5) 0.30231(2) 0.43115(6) 0.05919(13) Uani 1 1 d . . . N1 N 0.3684(6) 0.4833(3) 0.3238(8) 0.0696(17) Uani 1 1 d . . . N2 N 0.4735(7) 0.4471(3) 0.2613(8) 0.0733(18) Uani 1 1 d . . . C1 C 0.2669(8) 0.4544(3) 0.3851(10) 0.068(2) Uani 1 1 d . . . H1 H 0.2653 0.4124 0.3899 0.082 Uiso 1 1 calc R . . C2 C 0.1688(9) 0.4873(4) 0.4387(12) 0.086(3) Uani 1 1 d . . . H2 H 0.1000 0.4674 0.4778 0.103 Uiso 1 1 calc R . . C3 C 0.1708(8) 0.5493(3) 0.4356(11) 0.079(2) Uani 1 1 d . . . H3 H 0.1028 0.5712 0.4707 0.095 Uiso 1 1 calc R . . C4 C 0.2730(8) 0.5787(3) 0.3806(9) 0.0637(19) Uani 1 1 d . . . H4 H 0.2760 0.6207 0.3825 0.076 Uiso 1 1 calc R . . C5 C 0.3712(7) 0.5470(3) 0.3226(8) 0.0505(16) Uani 1 1 d . . . H5 H 0.4391 0.5673 0.2827 0.061 Uiso 1 1 calc R . . C6 C 0.5533(6) 0.4709(2) 0.1810(7) 0.0358(13) Uani 1 1 d . . . H6 H 0.5523 0.5121 0.1575 0.043 Uiso 1 1 calc R . . C7 C 0.6438(5) 0.4316(2) 0.1292(7) 0.0328(12) Uani 1 1 d . . . C8 C 0.7623(7) 0.4558(3) 0.1219(9) 0.0600(18) Uani 1 1 d . . . H8 H 0.7788 0.4959 0.1536 0.072 Uiso 1 1 calc R . . C9 C 0.8599(7) 0.4231(3) 0.0689(9) 0.0592(18) Uani 1 1 d . . . H9 H 0.9428 0.4405 0.0654 0.071 Uiso 1 1 calc R . . C10 C 0.8346(8) 0.3644(3) 0.0208(9) 0.065(2) Uani 1 1 d . . . H10 H 0.9008 0.3410 -0.0132 0.078 Uiso 1 1 calc R . . C11 C 0.7114(7) 0.3406(3) 0.0232(10) 0.066(2) Uani 1 1 d . . . H11 H 0.6918 0.3010 -0.0118 0.079 Uiso 1 1 calc R . . C12 C 0.6161(7) 0.3755(3) 0.0778(9) 0.0610(18) Uani 1 1 d . . . H12 H 0.5313 0.3595 0.0786 0.073 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.05299(15) 0.04041(14) 0.03824(14) -0.00014(10) 0.00981(10) 0.00048(10) I1 0.0577(3) 0.0357(2) 0.0639(3) -0.00616(19) 0.0120(2) -0.00102(18) I2 0.0532(3) 0.0498(2) 0.0601(3) -0.0018(2) 0.0101(2) -0.01148(19) I3 0.0643(3) 0.0574(3) 0.0546(3) 0.0029(2) 0.0081(2) 0.0225(2) N1 0.077(5) 0.063(4) 0.066(4) -0.003(3) 0.006(3) 0.001(3) N2 0.078(5) 0.066(4) 0.068(4) -0.013(3) -0.006(4) 0.014(4) C1 0.070(5) 0.045(4) 0.098(6) -0.006(4) 0.036(5) -0.009(4) C2 0.078(6) 0.060(5) 0.135(8) -0.022(5) 0.059(6) -0.016(4) C3 0.077(6) 0.054(5) 0.113(7) -0.022(5) 0.034(5) 0.002(4) C4 0.072(5) 0.046(4) 0.070(5) -0.006(4) 0.005(4) 0.008(4) C5 0.056(4) 0.042(4) 0.051(4) 0.000(3) 0.002(3) -0.001(3) C6 0.039(3) 0.027(3) 0.043(3) 0.007(2) 0.013(3) -0.003(2) C7 0.034(3) 0.028(3) 0.036(3) 0.001(2) 0.006(2) -0.005(2) C8 0.076(5) 0.046(4) 0.058(5) 0.001(3) 0.014(4) -0.005(4) C9 0.044(4) 0.069(5) 0.066(5) 0.006(4) 0.015(3) -0.004(3) C10 0.061(5) 0.060(5) 0.077(5) 0.012(4) 0.020(4) 0.015(4) C11 0.063(5) 0.049(4) 0.088(6) -0.002(4) 0.018(4) 0.002(4) C12 0.046(4) 0.059(4) 0.077(5) 0.005(4) 0.009(4) 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 3.1005(6) . ? Pb1 I3 3.1447(6) . ? Pb1 I2 3.1871(6) . ? Pb1 I3 3.2486(6) 4_566 ? Pb1 I2 3.2846(6) 4_566 ? I2 Pb1 3.2846(6) 4_565 ? I3 Pb1 3.2487(6) 4_565 ? N1 C1 1.381(9) . ? N1 C5 1.409(8) . ? N1 N2 1.496(8) . ? N2 C6 1.246(8) . ? C1 C2 1.368(10) . ? C2 C3 1.372(10) . ? C3 C4 1.369(10) . ? C4 C5 1.372(9) . ? C6 C7 1.386(7) . ? C7 C12 1.322(8) . ? C7 C8 1.327(8) . ? C8 C9 1.359(9) . ? C9 C10 1.367(10) . ? C10 C11 1.359(10) . ? C11 C12 1.374(9) . ? 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 I3 93.428(17) . . ? I1 Pb1 I2 97.332(15) . . ? I3 Pb1 I2 91.010(19) . . ? I1 Pb1 I3 85.779(16) . 4_566 ? I3 Pb1 I3 93.51(2) . 4_566 ? I2 Pb1 I3 174.356(14) . 4_566 ? I1 Pb1 I2 84.871(16) . 4_566 ? I3 Pb1 I2 177.973(14) . 4_566 ? I2 Pb1 I2 88.118(19) . 4_566 ? I3 Pb1 I2 87.470(19) 4_566 4_566 ? Pb1 I2 Pb1 77.296(17) . 4_565 ? Pb1 I3 Pb1 78.421(17) . 4_565 ? C1 N1 C5 118.9(6) . . ? C1 N1 N2 120.0(6) . . ? C5 N1 N2 121.1(6) . . ? C6 N2 N1 121.7(6) . . ? C2 C1 N1 120.2(7) . . ? C1 C2 C3 120.8(7) . . ? C4 C3 C2 119.8(7) . . ? C3 C4 C5 120.7(7) . . ? C4 C5 N1 119.6(7) . . ? N2 C6 C7 115.1(5) . . ? C12 C7 C8 120.4(6) . . ? C12 C7 C6 124.8(6) . . ? C8 C7 C6 114.5(5) . . ? C7 C8 C9 121.2(6) . . ? C8 C9 C10 119.2(7) . . ? C11 C10 C9 119.2(7) . . ? C10 C11 C12 119.4(7) . . ? C7 C12 C11 120.5(7) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.70 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.771 _refine_diff_density_min -0.739 _refine_diff_density_rms 0.136 #====================== data_mch3780404 _database_code_depnum_ccdc_archive 'CCDC 780404' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 I3 N2 Pb' _chemical_formula_weight 785.14 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -4.0753 8.5060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.8306(7) _cell_length_b 20.2084(14) _cell_length_c 7.9333(5) _cell_angle_alpha 90.00 _cell_angle_beta 98.925(6) _cell_angle_gamma 90.00 _cell_volume 1873.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4988 _cell_measurement_theta_min 2.1710 _cell_measurement_theta_max 62.8560 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.783 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384.0 _exptl_absorpt_coefficient_mu 56.236 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.06445 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number 10173 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9950 _diffrn_reflns_av_R_equivalents 0.0624 _diffrn_reflns_av_sigmaI/netI 0.0447 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 62.93 _reflns_number_total 2988 _reflns_number_gt 2298 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) ; _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. A 'rigid bond' restraint keyword 'delu' was used for C(13) and C(11) atoms. The potential molecule-accessible area in this structure was further calculated as 14.7 Ang^3 or 0.8% of the unit-cell volume by PLATON version 29-11-98, too smaller value indicates that all atomic sites have been identified. ; _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^)+(0.2500P)^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 2988 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.3591 _refine_ls_wR_factor_gt 0.3441 _refine_ls_goodness_of_fit_ref 1.065 _refine_ls_restrained_S_all 1.065 _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 Pb1 Pb 0.31421(9) 0.25221(4) 0.89741(13) 0.0504(6) Uani 1 1 d . . . I1 I 0.11399(15) 0.19415(9) 1.1130(2) 0.0635(7) Uani 1 1 d . . . I2 I 0.31816(14) 0.12315(9) 0.6325(2) 0.0592(6) Uani 1 1 d . . . I3 I 0.49310(15) 0.18244(10) 1.1964(2) 0.0654(7) Uani 1 1 d . . . N1 N -0.0511(19) 1.0501(10) 0.650(3) 0.053(5) Uani 1 1 d . . . N2 N 0.0277(19) 1.0039(9) 0.753(3) 0.058(6) Uani 1 1 d . . . C1 C -0.152(2) 1.0247(15) 0.602(4) 0.061(7) Uani 1 1 d . . . H1A H -0.1680 0.9818 0.6326 0.074 Uiso 1 1 calc R . . C2 C -0.236(3) 1.0634(15) 0.501(4) 0.073(8) Uani 1 1 d . . . H2B H -0.3116 1.0495 0.4768 0.087 Uiso 1 1 calc R . . C3 C -0.200(3) 1.1248(15) 0.438(4) 0.069(8) Uani 1 1 d . . . H3A H -0.2496 1.1501 0.3624 0.082 Uiso 1 1 calc R . . C4 C -0.089(3) 1.1459(15) 0.492(5) 0.082(9) Uani 1 1 d . . . H4A H -0.0640 1.1856 0.4512 0.098 Uiso 1 1 calc R . . C5 C -0.017(2) 1.1092(14) 0.604(4) 0.069(8) Uani 1 1 d . . . H5A H 0.0554 1.1251 0.6488 0.083 Uiso 1 1 calc R . . C6 C 0.106(2) 1.0289(12) 0.860(4) 0.059(7) Uani 1 1 d . . . H6A H 0.1104 1.0747 0.8716 0.071 Uiso 1 1 calc R . . C7 C 0.189(2) 0.9892(13) 0.961(3) 0.054(6) Uani 1 1 d . . . C8 C 0.292(2) 1.0154(14) 1.041(3) 0.059(7) Uani 1 1 d . . . H8A H 0.3055 1.0603 1.0293 0.071 Uiso 1 1 calc R . . C9 C 0.371(3) 0.979(2) 1.134(5) 0.088(10) Uani 1 1 d . . . H9A H 0.4371 0.9990 1.1923 0.106 Uiso 1 1 calc R . . C10 C 0.355(2) 0.9110(18) 1.142(4) 0.070(8) Uani 1 1 d . . . H10A H 0.4135 0.8854 1.2002 0.084 Uiso 1 1 calc R . . C11 C 0.256(3) 0.8797(14) 1.068(4) 0.062(7) Uani 1 1 d U . . C12 C 0.174(2) 0.9202(12) 0.970(3) 0.052(6) Uani 1 1 d . . . H12A H 0.1079 0.9010 0.9110 0.063 Uiso 1 1 calc R . . C13 C 0.239(3) 0.8055(15) 1.078(6) 0.117(18) Uani 1 1 d U . . H13A H 0.3029 0.7860 1.1496 0.176 Uiso 1 1 calc R . . H13B H 0.2313 0.7868 0.9660 0.176 Uiso 1 1 calc R . . H13C H 0.1702 0.7968 1.1258 0.176 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 0.0511(8) 0.0482(8) 0.0521(8) -0.0005(4) 0.0084(5) 0.0001(4) I1 0.0514(11) 0.0632(12) 0.0754(13) -0.0058(9) 0.0083(8) -0.0114(7) I2 0.0612(11) 0.0439(10) 0.0715(12) 0.0039(7) 0.0074(9) -0.0020(7) I3 0.0504(11) 0.0732(13) 0.0719(12) -0.0032(9) 0.0079(8) 0.0129(8) N1 0.068(13) 0.043(12) 0.050(11) -0.003(9) 0.013(10) 0.010(10) N2 0.054(11) 0.031(11) 0.089(17) 0.018(11) 0.007(11) 0.001(9) C1 0.045(14) 0.068(18) 0.075(18) 0.010(14) 0.019(13) 0.007(12) C2 0.062(17) 0.060(19) 0.09(2) 0.002(16) 0.006(15) -0.001(14) C3 0.068(18) 0.070(19) 0.063(16) 0.007(15) -0.005(13) 0.008(15) C4 0.09(2) 0.036(14) 0.12(3) 0.003(16) 0.01(2) 0.014(15) C5 0.057(16) 0.043(15) 0.10(2) 0.014(15) -0.002(15) -0.008(12) C6 0.065(16) 0.033(13) 0.081(18) -0.013(12) 0.018(14) -0.013(12) C7 0.061(15) 0.040(13) 0.062(15) 0.004(11) 0.011(12) 0.000(11) C8 0.058(15) 0.045(14) 0.073(17) 0.014(13) 0.005(13) -0.007(12) C9 0.068(19) 0.10(3) 0.09(2) 0.01(2) -0.005(17) -0.036(18) C10 0.047(15) 0.09(2) 0.075(19) -0.001(17) 0.015(13) 0.020(15) C11 0.079(19) 0.046(13) 0.062(16) 0.006(12) 0.014(14) 0.006(13) C12 0.046(13) 0.033(12) 0.074(16) 0.002(11) -0.003(11) 0.005(10) C13 0.10(3) 0.041(14) 0.19(5) 0.05(2) -0.04(3) 0.014(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 Pb1 I2 3.1300(19) 4_566 ? Pb1 I3 3.133(2) 4_565 ? Pb1 I1 3.196(2) 4_565 ? Pb1 I3 3.246(2) . ? Pb1 I1 3.3422(19) . ? Pb1 I2 3.354(2) . ? I1 Pb1 3.1964(19) 4_566 ? I2 Pb1 3.1300(19) 4_565 ? I3 Pb1 3.133(2) 4_566 ? N1 C1 1.30(4) . ? N1 C5 1.33(3) . ? N1 N2 1.47(3) . ? N2 C6 1.26(3) . ? C1 C2 1.41(4) . ? C2 C3 1.43(4) . ? C3 C4 1.38(5) . ? C4 C5 1.36(4) . ? C6 C7 1.42(4) . ? C7 C8 1.39(4) . ? C7 C12 1.41(4) . ? C8 C9 1.32(5) . ? C9 C10 1.40(5) . ? C10 C11 1.37(4) . ? C11 C12 1.41(4) . ? C11 C13 1.52(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 Pb1 I3 90.88(5) 4_566 4_565 ? I2 Pb1 I1 95.09(5) 4_566 4_565 ? I3 Pb1 I1 89.02(5) 4_565 4_565 ? I2 Pb1 I3 88.07(5) 4_566 . ? I3 Pb1 I3 98.03(6) 4_565 . ? I1 Pb1 I3 172.24(6) 4_565 . ? I2 Pb1 I1 85.63(5) 4_566 . ? I3 Pb1 I1 175.52(6) 4_565 . ? I1 Pb1 I1 88.50(6) 4_565 . ? I3 Pb1 I1 84.67(5) . . ? I2 Pb1 I2 176.97(6) 4_566 . ? I3 Pb1 I2 86.13(5) 4_565 . ? I1 Pb1 I2 84.39(5) 4_565 . ? I3 Pb1 I2 92.82(5) . . ? I1 Pb1 I2 97.33(5) . . ? Pb1 I1 Pb1 74.68(4) 4_566 . ? Pb1 I2 Pb1 75.36(4) 4_565 . ? Pb1 I3 Pb1 76.91(4) 4_566 . ? C1 N1 C5 125(3) . . ? C1 N1 N2 113(2) . . ? C5 N1 N2 122(2) . . ? C6 N2 N1 117(2) . . ? N1 C1 C2 119(3) . . ? C1 C2 C3 117(3) . . ? C4 C3 C2 119(3) . . ? C5 C4 C3 120(3) . . ? N1 C5 C4 119(3) . . ? N2 C6 C7 122(2) . . ? C8 C7 C12 118(2) . . ? C8 C7 C6 122(2) . . ? C12 C7 C6 120(2) . . ? C9 C8 C7 123(3) . . ? C8 C9 C10 119(3) . . ? C11 C10 C9 123(3) . . ? C10 C11 C12 116(3) . . ? C10 C11 C13 123(3) . . ? C12 C11 C13 121(3) . . ? C7 C12 C11 121(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 62.93 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 5.372 _refine_diff_density_min -3.870 _refine_diff_density_rms 0.567 # Attachment 'cifs-of-1-8.cif' data_mcn-780405 _database_code_depnum_ccdc_archive 'CCDC 780405' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 I3 N3 Pb' _chemical_formula_weight 796.13 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 'P 63' _symmetry_space_group_name_Hall 'P 6c' 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' _cell_length_a 20.114(2) _cell_length_b 20.114(2) _cell_length_c 7.9255(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2776.9(8) _cell_formula_units_Z 6 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5323 _cell_measurement_theta_min 3.4756 _cell_measurement_theta_max 25.4594 _exptl_crystal_description neddle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.856 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2100 _exptl_absorpt_coefficient_mu 14.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6022 _exptl_absorpt_correction_T_max 0.8718 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23426 _diffrn_reflns_av_R_equivalents 0.0666 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4223 _reflns_number_gt 2979 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. Special position constraints for Pb1, x = 0.0000, y = 0.0000, U22 = 1.0*U11,U23 = 0, U13 = 0,U12 = 0.5*U11, sof = 0.33333; Special position constraints for Pb2, x = 0.3333, y = 0.6667, U22 = 1.0*U11,U23 = 0, U13 = 0, U12 = 0.5*U11, sof = 0.33333; Special position constraints for Pb3, x = 0.3333, y = 0.6667, U22 = 1.0*U11,U23 = 0, U13 = 0, U12 = 0.5*U11, sof = 0.33333. ; _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^)+(0.1573P)^2^+244.4560P] 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 0.109(16) _refine_ls_number_reflns 4223 _refine_ls_number_parameters 181 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1045 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _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 Pb1 Pb 0.0000 0.0000 0.63377(15) 0.0322(3) Uani 1 3 d S . . Pb2 Pb 0.3333 0.6667 0.68380(17) 0.0390(4) Uani 1 3 d S . . Pb3 Pb 0.3333 0.6667 0.18569(16) 0.0359(4) Uani 1 3 d S . . I1 I 0.09670(8) 0.14304(7) 0.3908(2) 0.0424(3) Uani 1 1 d . . . I2 I 0.19276(8) 0.56470(8) 0.9354(2) 0.0461(3) Uani 1 1 d . . . I3 I 0.31413(9) 0.53058(8) 0.4330(2) 0.0492(4) Uani 1 1 d . . . N1 N 0.3426(10) 0.1622(12) 0.562(2) 0.044(5) Uani 1 1 d . . . N2 N 0.3355(12) 0.1902(15) 0.718(3) 0.064(7) Uani 1 1 d . . . N3 N 0.5645(17) 0.5499(17) 1.124(4) 0.083(8) Uani 1 1 d . . . C1 C 0.2768(15) 0.1248(16) 0.472(3) 0.053(7) Uani 1 1 d . . . H1A H 0.2320 0.1217 0.5131 0.064 Uiso 1 1 calc R . . C2 C 0.2755(17) 0.092(2) 0.321(4) 0.080(11) Uani 1 1 d . . . H2B H 0.2307 0.0680 0.2577 0.097 Uiso 1 1 calc R . . C3 C 0.3404(16) 0.0951(16) 0.266(3) 0.055(7) Uani 1 1 d . . . H3A H 0.3405 0.0724 0.1636 0.067 Uiso 1 1 calc R . . C4 C 0.4042(16) 0.1308(18) 0.357(4) 0.066(9) Uani 1 1 d . . . H4A H 0.4487 0.1328 0.3180 0.079 Uiso 1 1 calc R . . C5 C 0.4060(17) 0.1656(19) 0.512(3) 0.068(9) Uani 1 1 d . . . H5A H 0.4506 0.1900 0.5766 0.081 Uiso 1 1 calc R . . C6 C 0.3881(17) 0.2564(18) 0.759(4) 0.060(7) Uani 1 1 d . . . H6A H 0.4288 0.2823 0.6840 0.072 Uiso 1 1 calc R . . C7 C 0.3891(11) 0.2949(12) 0.914(3) 0.043(5) Uani 1 1 d . . . C8 C 0.4500(13) 0.3700(13) 0.944(4) 0.057(6) Uani 1 1 d . . . H8A H 0.4901 0.3931 0.8667 0.068 Uiso 1 1 calc R . . C9 C 0.4508(17) 0.4092(17) 1.085(3) 0.053(7) Uani 1 1 d . . . C10 C 0.3886(19) 0.3718(19) 1.203(4) 0.066(8) Uani 1 1 d . . . H10A H 0.3874 0.3988 1.2976 0.080 Uiso 1 1 calc R . . C11 C 0.3341(19) 0.301(2) 1.182(4) 0.079(10) Uani 1 1 d . . . H11A H 0.2975 0.2770 1.2662 0.094 Uiso 1 1 calc R . . C12 C 0.3294(16) 0.2607(15) 1.033(4) 0.057(7) Uani 1 1 d . . . H12A H 0.2874 0.2121 1.0136 0.068 Uiso 1 1 calc R . . C13 C 0.5117(18) 0.4843(17) 1.112(4) 0.056(7) 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 Pb1 0.0385(4) 0.0385(4) 0.0197(6) 0.000 0.000 0.0192(2) Pb2 0.0488(7) 0.0488(7) 0.0196(7) 0.000 0.000 0.0244(4) Pb3 0.0434(7) 0.0434(7) 0.0209(7) 0.000 0.000 0.0217(3) I1 0.0515(8) 0.0337(7) 0.0341(7) 0.0001(6) -0.0019(7) 0.0153(6) I2 0.0403(7) 0.0496(8) 0.0379(7) 0.0028(8) -0.0025(8) 0.0145(6) I3 0.0706(10) 0.0439(7) 0.0339(7) -0.0025(8) -0.0109(9) 0.0293(7) N1 0.025(10) 0.056(12) 0.038(11) -0.008(9) 0.001(8) 0.010(9) N2 0.036(13) 0.072(17) 0.056(16) -0.002(12) 0.009(11) 0.006(12) N3 0.08(2) 0.073(19) 0.10(2) -0.010(17) -0.007(17) 0.038(17) C1 0.049(14) 0.078(19) 0.044(17) -0.019(13) -0.005(11) 0.040(14) C2 0.045(17) 0.12(3) 0.07(2) -0.003(19) -0.012(14) 0.033(19) C3 0.061(18) 0.065(18) 0.041(15) -0.018(13) -0.005(13) 0.033(15) C4 0.043(15) 0.09(2) 0.051(18) -0.014(16) 0.005(13) 0.028(15) C5 0.048(17) 0.10(3) 0.028(13) 0.005(14) 0.002(11) 0.019(17) C6 0.060(18) 0.07(2) 0.053(16) 0.025(15) 0.021(14) 0.040(17) C7 0.035(10) 0.049(12) 0.031(14) 0.017(10) 0.006(10) 0.010(9) C8 0.052(13) 0.046(13) 0.068(16) -0.017(15) 0.005(16) 0.020(11) C9 0.08(2) 0.08(2) 0.027(12) -0.001(12) -0.010(12) 0.062(18) C10 0.07(2) 0.08(2) 0.048(17) -0.004(16) -0.004(15) 0.035(19) C11 0.06(2) 0.11(3) 0.07(2) -0.01(2) 0.001(16) 0.05(2) C12 0.052(16) 0.043(14) 0.066(18) 0.013(13) 0.014(14) 0.017(13) C13 0.071(19) 0.053(16) 0.068(18) -0.016(15) -0.020(16) 0.049(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 Pb1 I1 3.1894(17) 2 ? Pb1 I1 3.1894(17) 3 ? Pb1 I1 3.1894(17) . ? Pb1 I1 3.2581(17) 5 ? Pb1 I1 3.2581(17) 6 ? Pb1 I1 3.2581(17) 4 ? Pb2 I2 3.2214(18) 3_565 ? Pb2 I2 3.2214(18) . ? Pb2 I2 3.2214(18) 2_665 ? Pb2 I3 3.2458(18) 3_565 ? Pb2 I3 3.2458(18) 2_665 ? Pb2 I3 3.2458(18) . ? Pb3 I2 3.2151(18) 1_554 ? Pb3 I2 3.2151(18) 3_564 ? Pb3 I2 3.2151(18) 2_664 ? Pb3 I3 3.2290(18) 3_565 ? Pb3 I3 3.2290(18) 2_665 ? Pb3 I3 3.2290(18) . ? I1 Pb1 3.2581(17) 4_554 ? I2 Pb3 3.2151(18) 1_556 ? N1 C5 1.30(3) . ? N1 C1 1.36(3) . ? N1 N2 1.40(3) . ? N2 C6 1.26(4) . ? N3 C13 1.22(4) . ? C1 C2 1.35(4) . ? C2 C3 1.35(4) . ? C3 C4 1.33(4) . ? C4 C5 1.40(4) . ? C6 C7 1.45(4) . ? C7 C8 1.41(3) . ? C7 C12 1.41(3) . ? C8 C9 1.36(4) . ? C9 C13 1.41(4) . ? C9 C10 1.44(4) . ? C10 C11 1.30(5) . ? C11 C12 1.41(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I1 Pb1 I1 87.32(5) 2 3 ? I1 Pb1 I1 87.32(5) 2 . ? I1 Pb1 I1 87.32(5) 3 . ? I1 Pb1 I1 178.43(6) 2 5 ? I1 Pb1 I1 93.81(2) 3 5 ? I1 Pb1 I1 93.81(2) . 5 ? I1 Pb1 I1 93.81(2) 2 6 ? I1 Pb1 I1 178.43(6) 3 6 ? I1 Pb1 I1 93.81(2) . 6 ? I1 Pb1 I1 85.04(5) 5 6 ? I1 Pb1 I1 93.81(2) 2 4 ? I1 Pb1 I1 93.81(2) 3 4 ? I1 Pb1 I1 178.43(6) . 4 ? I1 Pb1 I1 85.04(5) 5 4 ? I1 Pb1 I1 85.04(5) 6 4 ? I2 Pb2 I2 85.72(5) 3_565 . ? I2 Pb2 I2 85.72(5) 3_565 2_665 ? I2 Pb2 I2 85.72(5) . 2_665 ? I2 Pb2 I3 98.38(4) 3_565 3_565 ? I2 Pb2 I3 89.85(4) . 3_565 ? I2 Pb2 I3 173.74(4) 2_665 3_565 ? I2 Pb2 I3 89.85(4) 3_565 2_665 ? I2 Pb2 I3 173.74(4) . 2_665 ? I2 Pb2 I3 98.38(4) 2_665 2_665 ? I3 Pb2 I3 86.42(5) 3_565 2_665 ? I2 Pb2 I3 173.74(4) 3_565 . ? I2 Pb2 I3 98.38(4) . . ? I2 Pb2 I3 89.85(4) 2_665 . ? I3 Pb2 I3 86.42(5) 3_565 . ? I3 Pb2 I3 86.42(5) 2_665 . ? I2 Pb3 I2 85.93(5) 1_554 3_564 ? I2 Pb3 I2 85.93(5) 1_554 2_664 ? I2 Pb3 I2 85.93(5) 3_564 2_664 ? I2 Pb3 I3 89.44(4) 1_554 3_565 ? I2 Pb3 I3 98.02(4) 3_564 3_565 ? I2 Pb3 I3 173.69(4) 2_664 3_565 ? I2 Pb3 I3 173.69(4) 1_554 2_665 ? I2 Pb3 I3 89.44(4) 3_564 2_665 ? I2 Pb3 I3 98.02(4) 2_664 2_665 ? I3 Pb3 I3 86.98(5) 3_565 2_665 ? I2 Pb3 I3 98.02(4) 1_554 . ? I2 Pb3 I3 173.69(4) 3_564 . ? I2 Pb3 I3 89.44(4) 2_664 . ? I3 Pb3 I3 86.98(5) 3_565 . ? I3 Pb3 I3 86.98(5) 2_665 . ? Pb1 I1 Pb1 75.84(3) . 4_554 ? Pb3 I2 Pb2 76.34(4) 1_556 . ? Pb3 I3 Pb2 75.14(4) . . ? C5 N1 C1 122(2) . . ? C5 N1 N2 123(2) . . ? C1 N1 N2 115.0(19) . . ? C6 N2 N1 117(2) . . ? N1 C1 C2 121(3) . . ? C3 C2 C1 119(3) . . ? C4 C3 C2 120(3) . . ? C3 C4 C5 122(3) . . ? N1 C5 C4 117(3) . . ? N2 C6 C7 124(3) . . ? C8 C7 C12 119(2) . . ? C8 C7 C6 119(2) . . ? C12 C7 C6 122(2) . . ? C9 C8 C7 121(3) . . ? C8 C9 C13 120(3) . . ? C8 C9 C10 118(3) . . ? C13 C9 C10 122(3) . . ? C11 C10 C9 122(3) . . ? C10 C11 C12 121(3) . . ? C11 C12 C7 119(3) . . ? N3 C13 C9 176(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.657 _refine_diff_density_min -3.434 _refine_diff_density_rms 0.326 #============== data_obr-780406 _database_code_depnum_ccdc_archive 'CCDC 780406' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Br I3 N2 Pb' _chemical_formula_weight 850.02 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 12.2054(9) _cell_length_b 8.1916(5) _cell_length_c 20.1750(11) _cell_angle_alpha 90.00 _cell_angle_beta 113.115(3) _cell_angle_gamma 90.00 _cell_volume 1855.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1850 _cell_measurement_theta_min 3.0196 _cell_measurement_theta_max 22.8870 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.043 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 16.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0700 _exptl_absorpt_correction_T_max 0.2937 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10292 _diffrn_reflns_av_R_equivalents 0.1199 _diffrn_reflns_av_sigmaI/netI 0.1068 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3629 _reflns_number_gt 2084 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. A 'rigid bond' restraint keyword 'delu' was used for Pb(1) and I(1) atoms. the potential molecule-accessible area in this structure was further calculated as 35.2 Ang^3 or 1.9% of the unit-cell volume by PLATON version 29-11-98, smaller value indicates all atomic sites have been identified. The PLATON/ADDSYM run indicates the space group P21/c is correct. ; _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^)+(0.0613P)^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 3629 _refine_ls_number_parameters 172 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0867 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1333 _refine_ls_wR_factor_gt 0.1235 _refine_ls_goodness_of_fit_ref 0.837 _refine_ls_restrained_S_all 0.837 _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 0.99791(5) 1.03184(7) 0.75210(3) 0.0482(2) Uani 1 1 d U . . I1 I 0.76520(9) 0.79434(12) 0.68206(5) 0.0555(3) Uani 1 1 d U . . I2 I 1.05835(9) 0.77962(11) 0.88085(5) 0.0503(3) Uani 1 1 d . . . I3 I 1.10383(9) 0.78965(11) 0.66687(5) 0.0502(3) Uani 1 1 d . . . Br1 Br 0.64040(15) 0.2952(2) 0.62611(9) 0.0703(5) Uani 1 1 d . . . C1 C 0.7242(17) 0.620(2) 0.8678(8) 0.063(5) Uani 1 1 d . . . H1 H 0.7422 0.6689 0.8318 0.076 Uiso 1 1 calc R . . C2 C 0.8048(16) 0.6226(19) 0.9383(10) 0.067(5) Uani 1 1 d . . . H2 H 0.8779 0.6737 0.9493 0.080 Uiso 1 1 calc R . . C3 C 0.7812(19) 0.554(2) 0.9910(10) 0.075(6) Uani 1 1 d . . . H3 H 0.8345 0.5622 1.0388 0.090 Uiso 1 1 calc R . . C4 C 0.679(2) 0.475(2) 0.9731(11) 0.092(7) Uani 1 1 d . . . H4 H 0.6645 0.4188 1.0089 0.111 Uiso 1 1 calc R . . C5 C 0.5907(18) 0.471(2) 0.9023(10) 0.073(5) Uani 1 1 d . . . H5 H 0.5171 0.4212 0.8909 0.088 Uiso 1 1 calc R . . C6 C 0.5553(12) 0.4805(16) 0.7341(7) 0.041(3) Uani 1 1 d . . . H6 H 0.6286 0.4288 0.7467 0.050 Uiso 1 1 calc R . . C7 C 0.4672(14) 0.4770(16) 0.6592(8) 0.046(4) Uani 1 1 d . . . C8 C 0.4917(12) 0.3972(16) 0.6045(8) 0.044(3) Uani 1 1 d . . . C9 C 0.4110(13) 0.3969(15) 0.5360(7) 0.045(3) Uani 1 1 d . . . H9 H 0.4311 0.3513 0.5000 0.054 Uiso 1 1 calc R . . C10 C 0.2991(16) 0.4630(19) 0.5181(9) 0.064(5) Uani 1 1 d . . . H10 H 0.2414 0.4542 0.4715 0.077 Uiso 1 1 calc R . . C11 C 0.2749(16) 0.5426(19) 0.5713(10) 0.069(5) Uani 1 1 d . . . H11 H 0.2014 0.5931 0.5596 0.083 Uiso 1 1 calc R . . C12 C 0.3582(15) 0.5481(18) 0.6415(9) 0.063(5) Uani 1 1 d . . . H12 H 0.3399 0.6004 0.6768 0.075 Uiso 1 1 calc R . . N1 N 0.6211(12) 0.5457(13) 0.8521(7) 0.047(3) Uani 1 1 d . . . N2 N 0.5298(12) 0.5551(16) 0.7814(7) 0.063(4) 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 Pb1 0.0625(4) 0.0416(3) 0.0478(4) 0.0051(2) 0.0295(3) 0.0118(3) I1 0.0503(6) 0.0614(6) 0.0544(6) 0.0046(5) 0.0201(5) -0.0022(5) I2 0.0623(7) 0.0455(5) 0.0414(5) 0.0013(4) 0.0186(5) -0.0075(5) I3 0.0634(7) 0.0393(5) 0.0665(7) 0.0027(5) 0.0455(5) 0.0023(5) Br1 0.0572(11) 0.0985(14) 0.0601(10) -0.0179(9) 0.0283(9) 0.0201(9) C1 0.101(15) 0.058(11) 0.046(10) 0.009(8) 0.046(10) 0.025(10) C2 0.071(12) 0.054(11) 0.092(14) 0.008(10) 0.050(11) 0.015(9) C3 0.108(18) 0.047(10) 0.065(13) -0.012(9) 0.028(12) 0.008(10) C4 0.16(2) 0.067(13) 0.067(14) 0.016(10) 0.057(15) 0.014(14) C5 0.099(16) 0.068(12) 0.066(12) 0.004(9) 0.046(12) -0.002(10) C6 0.037(8) 0.049(8) 0.046(9) 0.011(7) 0.025(7) 0.014(6) C7 0.063(11) 0.039(8) 0.048(9) -0.003(7) 0.032(8) -0.001(7) C8 0.045(9) 0.034(7) 0.055(9) 0.008(7) 0.022(7) 0.003(6) C9 0.055(10) 0.034(8) 0.041(8) 0.004(6) 0.013(7) 0.010(7) C10 0.073(13) 0.060(10) 0.046(10) 0.011(8) 0.009(9) 0.012(9) C11 0.058(12) 0.065(11) 0.084(13) 0.006(9) 0.027(10) 0.029(9) C12 0.072(12) 0.053(10) 0.064(11) -0.001(8) 0.027(10) 0.029(9) N1 0.059(9) 0.038(7) 0.051(8) -0.010(6) 0.029(7) 0.002(6) N2 0.067(10) 0.066(9) 0.052(8) -0.011(7) 0.020(7) 0.010(7) _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 3.1711(11) . ? Pb1 I3 3.2044(10) 2_756 ? Pb1 I3 3.2109(10) . ? Pb1 I2 3.2156(11) 2_756 ? Pb1 I1 3.2708(12) . ? Pb1 I1 3.4252(12) 2_756 ? I1 Pb1 3.4252(12) 2_746 ? I2 Pb1 3.2156(11) 2_746 ? I3 Pb1 3.2044(10) 2_746 ? Br1 C8 1.887(13) . ? C1 N1 1.32(2) . ? C1 C2 1.37(2) . ? C1 H1 0.9300 . ? C2 C3 1.33(2) . ? C2 H2 0.9300 . ? C3 C4 1.33(3) . ? C3 H3 0.9300 . ? C4 C5 1.41(3) . ? C4 H4 0.9300 . ? C5 N1 1.353(18) . ? C5 H5 0.9300 . ? C6 N2 1.271(16) . ? C6 C7 1.472(18) . ? C6 H6 0.9300 . ? C7 C12 1.37(2) . ? C7 C8 1.412(17) . ? C8 C9 1.346(17) . ? C9 C10 1.38(2) . ? C9 H9 0.9300 . ? C10 C11 1.38(2) . ? C10 H10 0.9300 . ? C11 C12 1.38(2) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? N1 N2 1.425(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 Pb1 I3 91.35(3) . 2_756 ? I2 Pb1 I3 91.32(3) . . ? I3 Pb1 I3 176.93(3) 2_756 . ? I2 Pb1 I2 177.99(3) . 2_756 ? I3 Pb1 I2 90.63(3) 2_756 2_756 ? I3 Pb1 I2 86.69(3) . 2_756 ? I2 Pb1 I1 81.35(3) . . ? I3 Pb1 I1 99.66(3) 2_756 . ? I3 Pb1 I1 82.24(3) . . ? I2 Pb1 I1 98.64(3) 2_756 . ? I2 Pb1 I1 101.65(3) . 2_756 ? I3 Pb1 I1 79.96(3) 2_756 2_756 ? I3 Pb1 I1 98.02(3) . 2_756 ? I2 Pb1 I1 78.38(3) 2_756 2_756 ? I1 Pb1 I1 176.98(3) . 2_756 ? Pb1 I1 Pb1 75.42(2) . 2_746 ? Pb1 I2 Pb1 79.81(2) . 2_746 ? Pb1 I3 Pb1 79.39(2) 2_746 . ? N1 C1 C2 119.1(15) . . ? N1 C1 H1 120.5 . . ? C2 C1 H1 120.5 . . ? C3 C2 C1 121.8(18) . . ? C3 C2 H2 119.1 . . ? C1 C2 H2 119.1 . . ? C4 C3 C2 117.7(19) . . ? C4 C3 H3 121.1 . . ? C2 C3 H3 121.1 . . ? C3 C4 C5 123.2(19) . . ? C3 C4 H4 118.4 . . ? C5 C4 H4 118.4 . . ? N1 C5 C4 115.1(18) . . ? N1 C5 H5 122.5 . . ? C4 C5 H5 122.5 . . ? N2 C6 C7 119.1(13) . . ? N2 C6 H6 120.5 . . ? C7 C6 H6 120.5 . . ? C12 C7 C8 118.5(14) . . ? C12 C7 C6 120.2(13) . . ? C8 C7 C6 121.2(13) . . ? C9 C8 C7 120.6(13) . . ? C9 C8 Br1 119.1(10) . . ? C7 C8 Br1 120.3(11) . . ? C8 C9 C10 121.2(14) . . ? C8 C9 H9 119.4 . . ? C10 C9 H9 119.4 . . ? C9 C10 C11 118.3(15) . . ? C9 C10 H10 120.8 . . ? C11 C10 H10 120.8 . . ? C10 C11 C12 121.0(16) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C7 C12 C11 120.1(15) . . ? C7 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C1 N1 C5 122.9(15) . . ? C1 N1 N2 120.9(13) . . ? C5 N1 N2 115.9(15) . . ? C6 N2 N1 113.5(12) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 Pb1 I1 Pb1 -46.88(2) . . . 2_746 ? I3 Pb1 I1 Pb1 -136.78(3) 2_756 . . 2_746 ? I3 Pb1 I1 Pb1 45.66(2) . . . 2_746 ? I2 Pb1 I1 Pb1 131.09(3) 2_756 . . 2_746 ? I1 Pb1 I1 Pb1 140.8(5) 2_756 . . 2_746 ? I3 Pb1 I2 Pb1 149.42(3) 2_756 . . 2_746 ? I3 Pb1 I2 Pb1 -32.09(3) . . . 2_746 ? I2 Pb1 I2 Pb1 -40.1(8) 2_756 . . 2_746 ? I1 Pb1 I2 Pb1 49.86(2) . . . 2_746 ? I1 Pb1 I2 Pb1 -130.55(3) 2_756 . . 2_746 ? I2 Pb1 I3 Pb1 32.26(3) . . . 2_746 ? I3 Pb1 I3 Pb1 -177.2(4) 2_756 . . 2_746 ? I2 Pb1 I3 Pb1 -148.02(3) 2_756 . . 2_746 ? I1 Pb1 I3 Pb1 -48.83(2) . . . 2_746 ? I1 Pb1 I3 Pb1 134.22(3) 2_756 . . 2_746 ? N1 C1 C2 C3 -1(2) . . . . ? C1 C2 C3 C4 3(3) . . . . ? C2 C3 C4 C5 -5(3) . . . . ? C3 C4 C5 N1 4(3) . . . . ? N2 C6 C7 C12 -2(2) . . . . ? N2 C6 C7 C8 179.3(13) . . . . ? C12 C7 C8 C9 3(2) . . . . ? C6 C7 C8 C9 -179.1(13) . . . . ? C12 C7 C8 Br1 -179.4(11) . . . . ? C6 C7 C8 Br1 -1.0(17) . . . . ? C7 C8 C9 C10 -5(2) . . . . ? Br1 C8 C9 C10 176.8(11) . . . . ? C8 C9 C10 C11 6(2) . . . . ? C9 C10 C11 C12 -4(2) . . . . ? C8 C7 C12 C11 -1(2) . . . . ? C6 C7 C12 C11 -179.0(14) . . . . ? C10 C11 C12 C7 1(3) . . . . ? C2 C1 N1 C5 0(2) . . . . ? C2 C1 N1 N2 172.9(12) . . . . ? C4 C5 N1 C1 -1(2) . . . . ? C4 C5 N1 N2 -175.0(14) . . . . ? C7 C6 N2 N1 178.4(12) . . . . ? C1 N1 N2 C6 68.0(16) . . . . ? C5 N1 N2 C6 -118.3(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 2.544 _refine_diff_density_min -2.314 _refine_diff_density_rms 0.339 #============== data_ocl-780407 _database_code_depnum_ccdc_archive 'CCDC 780407' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cl I3 N2 Pb' _chemical_formula_weight 805.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 12.0905(5) _cell_length_b 8.2004(3) _cell_length_c 19.9568(10) _cell_angle_alpha 90.00 _cell_angle_beta 112.369(4) _cell_angle_gamma 90.00 _cell_volume 1829.77(14) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2302 _cell_measurement_theta_min 3.1059 _cell_measurement_theta_max 24.1293 _exptl_crystal_description neddle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.924 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 14.417 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0522 _exptl_absorpt_correction_T_max 0.3266 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10910 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3567 _reflns_number_gt 2892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0467P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00183(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3567 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 0.50235(2) 0.54692(3) 0.753301(13) 0.04225(12) Uani 1 1 d . . . I1 I 0.73630(4) 0.78581(6) 0.81684(3) 0.05053(16) Uani 1 1 d . . . I2 I 0.39604(4) 0.79582(5) 0.83524(3) 0.04332(15) Uani 1 1 d . . . I3 I 0.55860(4) 0.29243(5) 0.88215(2) 0.04452(15) Uani 1 1 d . . . Cl1 Cl 0.86363(19) 0.2931(3) 0.87019(12) 0.0650(6) Uani 1 1 d . . . N1 N 0.8781(6) 0.5443(7) 0.6443(3) 0.0438(15) Uani 1 1 d . . . N2 N 0.9675(6) 0.5489(8) 0.7154(3) 0.0588(19) Uani 1 1 d . . . C1 C 0.9065(8) 0.4671(9) 0.5934(4) 0.056(2) Uani 1 1 d . . . H1 H 0.9793 0.4133 0.6061 0.067 Uiso 1 1 calc R . . C2 C 0.8280(9) 0.4686(11) 0.5234(5) 0.067(3) Uani 1 1 d . . . H2 H 0.8464 0.4153 0.4878 0.080 Uiso 1 1 calc R . . C3 C 0.7226(8) 0.5484(10) 0.5058(4) 0.058(2) Uani 1 1 d . . . H3 H 0.6691 0.5508 0.4578 0.070 Uiso 1 1 calc R . . C4 C 0.6946(7) 0.6238(11) 0.5569(4) 0.057(2) Uani 1 1 d . . . H4 H 0.6218 0.6776 0.5445 0.068 Uiso 1 1 calc R . . C5 C 0.7754(7) 0.6211(10) 0.6287(4) 0.0464(17) Uani 1 1 d . . . H5 H 0.7573 0.6724 0.6648 0.056 Uiso 1 1 calc R . . C6 C 0.9410(6) 0.4759(8) 0.7624(4) 0.0409(16) Uani 1 1 d . . . H6 H 0.8673 0.4241 0.7495 0.049 Uiso 1 1 calc R . . C7 C 1.0268(6) 0.4722(8) 0.8382(3) 0.0376(15) Uani 1 1 d . . . C8 C 0.9990(6) 0.3915(8) 0.8913(3) 0.0382(15) Uani 1 1 d . . . C9 C 1.0800(7) 0.3896(9) 0.9629(4) 0.0459(18) Uani 1 1 d . . . H9 H 1.0604 0.3363 0.9981 0.055 Uiso 1 1 calc R . . C10 C 1.1879(7) 0.4654(10) 0.9817(4) 0.057(2) Uani 1 1 d . . . H10 H 1.2417 0.4651 1.0297 0.068 Uiso 1 1 calc R . . C11 C 1.2169(8) 0.5430(10) 0.9289(5) 0.062(2) Uani 1 1 d . . . H11 H 1.2909 0.5937 0.9415 0.075 Uiso 1 1 calc R . . C12 C 1.1382(7) 0.5457(9) 0.8587(4) 0.051(2) Uani 1 1 d . . . H12 H 1.1595 0.5976 0.8240 0.062 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 0.0474(2) 0.04249(19) 0.03765(19) 0.00422(11) 0.01710(14) 0.01149(12) I1 0.0357(3) 0.0675(4) 0.0436(3) -0.0060(2) 0.0097(2) -0.0014(2) I2 0.0459(3) 0.0408(3) 0.0536(3) 0.0001(2) 0.0306(2) 0.0009(2) I3 0.0487(3) 0.0464(3) 0.0305(3) 0.0012(2) 0.0062(2) -0.0083(2) Cl1 0.0418(11) 0.1012(18) 0.0518(12) 0.0213(11) 0.0176(9) -0.0158(11) N1 0.044(4) 0.049(4) 0.037(3) 0.005(3) 0.014(3) -0.011(3) N2 0.049(4) 0.082(5) 0.035(4) 0.013(3) 0.005(3) -0.019(4) C1 0.069(6) 0.049(5) 0.049(5) -0.006(4) 0.021(4) 0.005(4) C2 0.089(7) 0.063(6) 0.048(5) -0.018(4) 0.025(5) -0.001(5) C3 0.071(6) 0.060(5) 0.032(4) -0.002(4) 0.007(4) -0.019(4) C4 0.048(5) 0.071(6) 0.050(5) 0.010(4) 0.017(4) -0.011(4) C5 0.047(4) 0.060(5) 0.039(4) -0.002(4) 0.024(3) -0.010(4) C6 0.037(4) 0.042(4) 0.048(4) 0.000(3) 0.019(3) -0.008(3) C7 0.042(4) 0.037(4) 0.031(4) 0.000(3) 0.010(3) -0.003(3) C8 0.036(4) 0.040(4) 0.040(4) -0.002(3) 0.016(3) 0.004(3) C9 0.055(5) 0.050(5) 0.035(4) 0.002(3) 0.020(3) 0.009(4) C10 0.053(5) 0.058(5) 0.041(5) -0.006(4) -0.001(4) -0.009(4) C11 0.052(5) 0.064(6) 0.060(5) 0.005(4) 0.009(4) -0.022(4) C12 0.047(5) 0.053(5) 0.047(5) 0.009(4) 0.010(4) -0.017(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 I2 3.1767(5) . ? Pb1 I3 3.1778(5) . ? Pb1 I3 3.2229(5) 2_656 ? Pb1 I2 3.2440(5) 2_646 ? Pb1 I1 3.2736(6) . ? I2 Pb1 3.2440(5) 2_656 ? I3 Pb1 3.2229(5) 2_646 ? Cl1 C8 1.727(7) . ? N1 C5 1.320(9) . ? N1 C1 1.348(9) . ? N1 N2 1.419(8) . ? N2 C6 1.255(8) . ? C1 C2 1.357(11) . ? C1 H1 0.9300 . ? C2 C3 1.355(12) . ? C2 H2 0.9300 . ? C3 C4 1.341(10) . ? C3 H3 0.9300 . ? C4 C5 1.394(10) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.473(9) . ? C6 H6 0.9300 . ? C7 C12 1.387(10) . ? C7 C8 1.396(9) . ? C8 C9 1.391(9) . ? C9 C10 1.363(11) . ? C9 H9 0.9300 . ? C10 C11 1.387(11) . ? C10 H10 0.9300 . ? C11 C12 1.360(11) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 Pb1 I3 90.537(14) . . ? I2 Pb1 I3 91.272(14) . 2_656 ? I3 Pb1 I3 177.580(15) . 2_656 ? I2 Pb1 I2 178.155(10) . 2_646 ? I3 Pb1 I2 90.865(14) . 2_646 ? I3 Pb1 I2 87.294(13) 2_656 2_646 ? I2 Pb1 I1 82.840(14) . . ? I3 Pb1 I1 101.084(15) . . ? I3 Pb1 I1 80.742(14) 2_656 . ? I2 Pb1 I1 98.065(14) 2_646 . ? Pb1 I2 Pb1 79.407(10) . 2_656 ? Pb1 I3 Pb1 79.710(11) . 2_646 ? C5 N1 C1 122.2(7) . . ? C5 N1 N2 120.9(6) . . ? C1 N1 N2 116.8(7) . . ? C6 N2 N1 114.8(6) . . ? N1 C1 C2 119.5(8) . . ? N1 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C3 C2 C1 119.4(8) . . ? C3 C2 H2 120.3 . . ? C1 C2 H2 120.3 . . ? C4 C3 C2 120.7(8) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 119.6(8) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 118.6(7) . . ? N1 C5 H5 120.7 . . ? C4 C5 H5 120.7 . . ? N2 C6 C7 119.8(6) . . ? N2 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C12 C7 C8 117.9(6) . . ? C12 C7 C6 121.4(6) . . ? C8 C7 C6 120.7(6) . . ? C9 C8 C7 120.5(7) . . ? C9 C8 Cl1 118.5(5) . . ? C7 C8 Cl1 121.1(5) . . ? C10 C9 C8 120.2(7) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 119.5(7) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 120.7(8) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C7 121.2(7) . . ? C11 C12 H12 119.4 . . ? C7 C12 H12 119.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I3 Pb1 I2 Pb1 149.914(16) . . . 2_656 ? I3 Pb1 I2 Pb1 -31.694(12) 2_656 . . 2_656 ? I2 Pb1 I2 Pb1 -70.7(5) 2_646 . . 2_656 ? I1 Pb1 I2 Pb1 48.810(12) . . . 2_656 ? I2 Pb1 I3 Pb1 147.156(15) . . . 2_646 ? I3 Pb1 I3 Pb1 8.8(2) 2_656 . . 2_646 ? I2 Pb1 I3 Pb1 -31.643(12) 2_646 . . 2_646 ? I1 Pb1 I3 Pb1 -130.035(14) . . . 2_646 ? C5 N1 N2 C6 67.6(9) . . . . ? C1 N1 N2 C6 -116.6(8) . . . . ? C5 N1 C1 C2 0.5(11) . . . . ? N2 N1 C1 C2 -175.3(7) . . . . ? N1 C1 C2 C3 0.4(13) . . . . ? C1 C2 C3 C4 -0.8(14) . . . . ? C2 C3 C4 C5 0.5(12) . . . . ? C1 N1 C5 C4 -0.8(11) . . . . ? N2 N1 C5 C4 174.8(6) . . . . ? C3 C4 C5 N1 0.3(11) . . . . ? N1 N2 C6 C7 180.0(6) . . . . ? N2 C6 C7 C12 -1.2(11) . . . . ? N2 C6 C7 C8 -180.0(7) . . . . ? C12 C7 C8 C9 1.7(10) . . . . ? C6 C7 C8 C9 -179.5(7) . . . . ? C12 C7 C8 Cl1 -178.6(6) . . . . ? C6 C7 C8 Cl1 0.1(9) . . . . ? C7 C8 C9 C10 -0.6(11) . . . . ? Cl1 C8 C9 C10 179.8(6) . . . . ? C8 C9 C10 C11 -0.7(12) . . . . ? C9 C10 C11 C12 0.8(13) . . . . ? C10 C11 C12 C7 0.5(13) . . . . ? C8 C7 C12 C11 -1.7(12) . . . . ? C6 C7 C12 C11 179.5(8) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.051 _refine_diff_density_min -1.022 _refine_diff_density_rms 0.161 #================ data_pbr-780408 _database_code_depnum_ccdc_archive 'CCDC 780408' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Br I3 N2 Pb' _chemical_formula_weight 850.02 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' Br Br -0.2901 2.4595 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/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 13.8838(5) _cell_length_b 16.4673(6) _cell_length_c 7.8911(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.357(3) _cell_angle_gamma 90.00 _cell_volume 1804.10(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2618 _cell_measurement_theta_min 2.1071 _cell_measurement_theta_max 27.4118 _exptl_crystal_description neddle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.130 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 16.689 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0263 _exptl_absorpt_correction_T_max 0.0980 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11042 _diffrn_reflns_av_R_equivalents 0.0614 _diffrn_reflns_av_sigmaI/netI 0.0496 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3523 _reflns_number_gt 2702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. A 'rigid bond' restraint keyword 'delu' was used for N(1) and N(2) atoms. ; _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^)+(0.0465P)^2^+289.9129P] 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 0.0012(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3523 _refine_ls_number_parameters 169 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1065 _refine_ls_R_factor_gt 0.0931 _refine_ls_wR_factor_ref 0.2571 _refine_ls_wR_factor_gt 0.2537 _refine_ls_goodness_of_fit_ref 1.162 _refine_ls_restrained_S_all 1.162 _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 Pb1 Pb 0.12916(9) 0.75181(8) 0.55641(16) 0.0382(4) Uani 1 1 d . . . I1 I -0.02847(16) 0.66604(15) 0.8009(3) 0.0457(6) Uani 1 1 d . . . I2 I 0.28718(16) 0.67245(16) 0.8030(3) 0.0480(6) Uani 1 1 d . . . I3 I 0.12548(18) 0.59575(13) 0.3141(3) 0.0446(6) Uani 1 1 d . . . Br1 Br 0.5452(3) 0.1174(3) 1.3592(6) 0.0690(12) Uani 1 1 d . . . N1 N 0.247(2) 0.1100(18) 0.435(4) 0.056(8) Uani 1 1 d GU . . N2 N 0.310(3) 0.125(2) 0.597(5) 0.064(9) Uani 1 1 d U . . C1 C 0.195(2) 0.0449(18) 0.419(4) 0.059(10) Uani 1 1 d G . . H1B H 0.1934 0.0055 0.5036 0.071 Uiso 1 1 calc R . . C2 C 0.1433(19) 0.0369(17) 0.277(3) 0.062(11) Uani 1 1 d G . . H2A H 0.1054 -0.0090 0.2604 0.075 Uiso 1 1 calc R . . C3 C 0.146(2) 0.0946(17) 0.159(3) 0.073(15) Uani 1 1 d G . . H3A H 0.1103 0.0890 0.0601 0.087 Uiso 1 1 calc R . . C4 C 0.200(2) 0.1603(15) 0.183(3) 0.052(9) Uani 1 1 d G . . H4A H 0.2023 0.2007 0.1010 0.062 Uiso 1 1 calc R . . C5 C 0.252(2) 0.1683(16) 0.325(4) 0.061(11) Uani 1 1 d G . . H5A H 0.2896 0.2139 0.3451 0.073 Uiso 1 1 calc R . . C6 C 0.312(2) 0.074(2) 0.706(5) 0.051(9) Uani 1 1 d . . . H6A H 0.2764 0.0271 0.6924 0.062 Uiso 1 1 calc R . . C7 C 0.372(2) 0.085(2) 0.867(5) 0.045(8) Uani 1 1 d . . . C8 C 0.364(2) 0.029(2) 0.991(4) 0.048(9) Uani 1 1 d . . . H8A H 0.3233 -0.0154 0.9738 0.058 Uiso 1 1 calc R . . C9 C 0.412(3) 0.036(2) 1.138(6) 0.059(11) Uani 1 1 d . . . H9A H 0.4043 -0.0027 1.2233 0.071 Uiso 1 1 calc R . . C10 C 0.474(2) 0.102(2) 1.159(5) 0.056(10) Uani 1 1 d . . . C11 C 0.484(3) 0.157(2) 1.024(6) 0.061(11) Uani 1 1 d . . . H11A H 0.5271 0.2002 1.0340 0.073 Uiso 1 1 calc R . . C12 C 0.433(3) 0.149(2) 0.883(5) 0.053(9) Uani 1 1 d . . . H12A H 0.4395 0.1868 0.7960 0.064 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 0.0400(7) 0.0443(7) 0.0302(6) -0.0004(5) -0.0012(4) -0.0005(5) I1 0.0376(12) 0.0512(14) 0.0483(13) -0.0040(10) 0.0022(9) -0.0073(10) I2 0.0363(12) 0.0612(15) 0.0465(13) -0.0030(11) -0.0037(9) 0.0107(10) I3 0.0518(13) 0.0383(11) 0.0436(12) -0.0009(10) 0.0005(9) 0.0062(10) Br1 0.068(3) 0.066(3) 0.073(3) -0.012(2) -0.013(2) -0.003(2) N1 0.062(19) 0.036(16) 0.069(18) -0.013(15) 0.042(13) -0.007(14) N2 0.06(2) 0.040(18) 0.09(2) -0.003(19) 0.015(16) -0.011(15) C1 0.06(3) 0.06(2) 0.05(2) 0.012(19) -0.005(19) -0.01(2) C2 0.06(2) 0.07(3) 0.06(3) -0.02(2) 0.003(19) -0.02(2) C3 0.07(3) 0.10(4) 0.05(2) 0.04(2) 0.01(2) 0.04(3) C4 0.07(2) 0.016(15) 0.07(3) 0.006(16) 0.00(2) 0.010(15) C5 0.05(2) 0.05(2) 0.09(3) 0.03(2) -0.01(2) 0.008(18) C6 0.033(18) 0.037(19) 0.08(3) 0.001(19) -0.010(17) -0.010(15) C7 0.029(16) 0.028(16) 0.08(3) 0.009(17) 0.008(16) 0.002(13) C8 0.033(17) 0.06(2) 0.05(2) -0.018(18) 0.003(15) -0.005(16) C9 0.05(2) 0.05(2) 0.08(3) 0.02(2) 0.02(2) -0.007(18) C10 0.026(16) 0.06(2) 0.08(3) -0.03(2) -0.005(16) -0.006(16) C11 0.07(3) 0.03(2) 0.07(3) 0.000(19) 0.01(2) -0.025(19) C12 0.04(2) 0.05(2) 0.07(2) -0.007(19) -0.014(18) -0.001(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 Pb1 I2 3.202(3) . ? Pb1 I3 3.203(3) . ? Pb1 I2 3.229(3) 4_575 ? Pb1 I3 3.231(3) 4_576 ? Pb1 I1 3.249(3) . ? Pb1 I1 3.260(3) 4_575 ? I1 Pb1 3.260(3) 4_576 ? I2 Pb1 3.229(3) 4_576 ? I3 Pb1 3.231(3) 4_575 ? Br1 C10 1.87(4) . ? N1 C5 1.29(4) . ? N1 C1 1.30(4) . ? N1 N2 1.57(5) . ? N2 C6 1.20(5) . ? C1 C2 1.331(18) . ? C1 H1B 0.9300 . ? C2 C3 1.331(18) . ? C2 H2A 0.9300 . ? C3 C4 1.331(18) . ? C3 H3A 0.9300 . ? C4 C5 1.331(18) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.52(5) . ? C6 H6A 0.9300 . ? C7 C8 1.35(5) . ? C7 C12 1.37(5) . ? C8 C9 1.34(5) . ? C8 H8A 0.9300 . ? C9 C10 1.40(5) . ? C9 H9A 0.9300 . ? C10 C11 1.41(6) . ? C11 C12 1.31(6) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 Pb1 I3 92.50(7) . . ? I2 Pb1 I2 93.92(8) . 4_575 ? I3 Pb1 I2 87.05(7) . 4_575 ? I2 Pb1 I3 87.03(7) . 4_576 ? I3 Pb1 I3 177.01(9) . 4_576 ? I2 Pb1 I3 95.92(7) 4_575 4_576 ? I2 Pb1 I1 85.60(7) . . ? I3 Pb1 I1 89.85(7) . . ? I2 Pb1 I1 176.84(8) 4_575 . ? I3 Pb1 I1 87.17(7) 4_576 . ? I2 Pb1 I1 178.91(8) . 4_575 ? I3 Pb1 I1 87.46(7) . 4_575 ? I2 Pb1 I1 84.99(6) 4_575 4_575 ? I3 Pb1 I1 93.08(7) 4_576 4_575 ? I1 Pb1 I1 95.48(8) . 4_575 ? Pb1 I1 Pb1 74.63(5) . 4_576 ? Pb1 I2 Pb1 75.70(5) . 4_576 ? Pb1 I3 Pb1 75.65(5) . 4_575 ? C5 N1 C1 126(4) . . ? C5 N1 N2 113(3) . . ? C1 N1 N2 121(3) . . ? C6 N2 N1 119(3) . . ? N1 C1 C2 117(2) . . ? N1 C1 H1B 121.4 . . ? C2 C1 H1B 121.4 . . ? C3 C2 C1 120.0 . . ? C3 C2 H2A 120.0 . . ? C1 C2 H2A 120.0 . . ? C2 C3 C4 120.0 . . ? C2 C3 H3A 120.0 . . ? C4 C3 H3A 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 H4A 120.0 . . ? C3 C4 H4A 120.0 . . ? N1 C5 C4 117(2) . . ? N1 C5 H5A 121.4 . . ? C4 C5 H5A 121.4 . . ? N2 C6 C7 122(3) . . ? N2 C6 H6A 119.0 . . ? C7 C6 H6A 119.0 . . ? C8 C7 C12 121(4) . . ? C8 C7 C6 119(3) . . ? C12 C7 C6 120(3) . . ? C9 C8 C7 122(4) . . ? C9 C8 H8A 119.1 . . ? C7 C8 H8A 119.1 . . ? C8 C9 C10 118(4) . . ? C8 C9 H9A 120.9 . . ? C10 C9 H9A 120.9 . . ? C9 C10 C11 118(4) . . ? C9 C10 Br1 122(4) . . ? C11 C10 Br1 120(3) . . ? C12 C11 C10 121(4) . . ? C12 C11 H11A 119.4 . . ? C10 C11 H11A 119.4 . . ? C11 C12 C7 119(4) . . ? C11 C12 H12A 120.4 . . ? C7 C12 H12A 120.4 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 Pb1 I1 Pb1 44.86(6) . . . 4_576 ? I3 Pb1 I1 Pb1 137.37(7) . . . 4_576 ? I2 Pb1 I1 Pb1 126.3(14) 4_575 . . 4_576 ? I3 Pb1 I1 Pb1 -42.37(6) 4_576 . . 4_576 ? I1 Pb1 I1 Pb1 -135.20(9) 4_575 . . 4_576 ? I3 Pb1 I2 Pb1 -134.79(7) . . . 4_576 ? I2 Pb1 I2 Pb1 137.99(9) 4_575 . . 4_576 ? I3 Pb1 I2 Pb1 42.25(6) 4_576 . . 4_576 ? I1 Pb1 I2 Pb1 -45.13(5) . . . 4_576 ? I1 Pb1 I2 Pb1 138(4) 4_575 . . 4_576 ? I2 Pb1 I3 Pb1 -136.05(6) . . . 4_575 ? I2 Pb1 I3 Pb1 -42.25(6) 4_575 . . 4_575 ? I3 Pb1 I3 Pb1 143.2(18) 4_576 . . 4_575 ? I1 Pb1 I3 Pb1 138.36(6) . . . 4_575 ? I1 Pb1 I3 Pb1 42.86(6) 4_575 . . 4_575 ? C5 N1 N2 C6 -179(4) . . . . ? C1 N1 N2 C6 2(5) . . . . ? C5 N1 C1 C2 1(5) . . . . ? N2 N1 C1 C2 -180(2) . . . . ? N1 C1 C2 C3 0(2) . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C1 N1 C5 C4 -1(5) . . . . ? N2 N1 C5 C4 180(2) . . . . ? C3 C4 C5 N1 0(2) . . . . ? N1 N2 C6 C7 -180(3) . . . . ? N2 C6 C7 C8 174(4) . . . . ? N2 C6 C7 C12 -7(6) . . . . ? C12 C7 C8 C9 3(6) . . . . ? C6 C7 C8 C9 -178(3) . . . . ? C7 C8 C9 C10 -2(6) . . . . ? C8 C9 C10 C11 -1(6) . . . . ? C8 C9 C10 Br1 180(3) . . . . ? C9 C10 C11 C12 2(6) . . . . ? Br1 C10 C11 C12 -178(3) . . . . ? C10 C11 C12 C7 -1(6) . . . . ? C8 C7 C12 C11 -2(6) . . . . ? C6 C7 C12 C11 -180(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 4.526 _refine_diff_density_min -4.606 _refine_diff_density_rms 0.427 # Attachment 'pch3.cif' data_pch3 _database_code_depnum_ccdc_archive 'CCDC 780409' #TrackingRef 'pch3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 I3 N2 Pb' _chemical_formula_weight 785.15 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 'P 21/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 13.819(10) _cell_length_b 16.772(12) _cell_length_c 7.911(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1834(2) _cell_formula_units_Z 5 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3316 _cell_measurement_theta_min 2.8531 _cell_measurement_theta_max 28.9400 _exptl_crystal_description neddle _exptl_crystal_colour yellow-red _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.844 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 14.239 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.25015 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.46 (release 27-08-2009 CrysAlis171 .NET) (compiled Aug 27 2009,17:19:36) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 296(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 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8207 _diffrn_reflns_av_R_equivalents 0.3320 _diffrn_reflns_av_sigmaI/netI 0.2169 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3228 _reflns_number_gt 2076 _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^)+(0.4500P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.011(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3206 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2238 _refine_ls_R_factor_gt 0.1998 _refine_ls_wR_factor_ref 0.5764 _refine_ls_wR_factor_gt 0.5484 _refine_ls_goodness_of_fit_ref 1.153 _refine_ls_restrained_S_all 1.153 _refine_ls_shift/su_max 0.441 _refine_ls_shift/su_mean 0.006 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 0.37094(13) 0.25089(8) 0.9438(2) 0.0453(11) Uani 1 1 d . . . I1 I 0.2118(2) 0.17447(18) 0.6954(4) 0.0540(12) Uani 1 1 d . . . I2 I 0.3710(2) 0.09767(17) 1.1897(3) 0.0534(12) Uani 1 1 d . . . I3 I 0.5293(2) 0.16479(18) 0.7013(4) 0.0540(12) Uani 1 1 d . . . N2 N 0.818(4) 0.121(2) 0.583(6) 0.086(15) Uani 1 1 d . . . N1 N 0.752(2) 0.1109(16) 0.442(4) 0.076(15) Uani 1 1 d G . . C1 C 0.748(2) 0.1686(17) 0.321(4) 0.083(19) Uani 1 1 d G . . H1A H 0.7870 0.2137 0.3306 0.100 Uiso 1 1 calc R . . C2 C 0.687(3) 0.160(2) 0.187(4) 0.073(16) Uani 1 1 d G . . H2B H 0.6845 0.1998 0.1046 0.088 Uiso 1 1 calc R . . C3 C 0.630(2) 0.0943(14) 0.174(5) 0.13(4) Uani 1 1 d G . . H3A H 0.5887 0.0887 0.0821 0.158 Uiso 1 1 calc R . . C4 C 0.634(2) 0.0366(11) 0.295(5) 0.76(16) Uani 1 1 d G . . H4A H 0.5954 -0.0085 0.2856 0.907 Uiso 1 1 calc R . . C5 C 0.695(2) 0.0449(16) 0.429(4) 0.067(13) Uani 1 1 d G . . H5A H 0.6978 0.0055 0.5116 0.080 Uiso 1 1 calc R . . C6 C 0.800(5) 0.083(3) 0.704(6) 0.081(17) Uani 1 1 d . . . H6 H 0.7466 0.0498 0.7054 0.097 Uiso 1 1 calc R . . C7 C 0.874(2) 0.0905(19) 0.880(4) 0.060(13) Uani 1 1 d G . . C8 C 0.862(2) 0.0372(18) 1.007(4) 0.15(4) Uani 1 1 d G . . H8A H 0.8169 -0.0037 0.9955 0.180 Uiso 1 1 calc R . . C9 C 0.915(3) 0.044(2) 1.150(4) 0.066(14) Uani 1 1 d G . . H9A H 0.9066 0.0070 1.2372 0.080 Uiso 1 1 calc R . . C10 C 0.981(2) 0.103(3) 1.166(4) 0.18(5) Uani 1 1 d G . . C11 C 0.9931(17) 0.156(2) 1.039(5) 0.11(3) Uani 1 1 d G . . H11A H 1.0381 0.1974 1.0504 0.130 Uiso 1 1 calc R . . C12 C 0.940(2) 0.1501(19) 0.896(5) 0.16(5) Uani 1 1 d G . . H12A H 0.9484 0.1867 0.8086 0.186 Uiso 1 1 calc R . . C13 C 1.038(5) 0.110(4) 1.320(8) 0.10(2) Uani 1 1 d . . . H13A H 1.0809 0.1545 1.3105 0.154 Uiso 1 1 calc R . . H13B H 1.0745 0.0620 1.3359 0.154 Uiso 1 1 calc R . . H13C H 0.9954 0.1177 1.4146 0.154 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 0.0696(18) 0.0496(15) 0.0166(13) 0.0005(5) -0.0113(8) 0.0007(6) I1 0.062(2) 0.067(2) 0.0323(18) -0.0004(12) -0.0148(12) -0.0078(13) I2 0.085(2) 0.0420(18) 0.0328(18) -0.0015(10) -0.0093(14) -0.0064(12) I3 0.068(2) 0.0556(19) 0.0382(18) 0.0034(12) -0.0092(13) 0.0072(13) N2 0.16(4) 0.04(2) 0.05(3) 0.03(2) -0.04(3) -0.04(2) N1 0.14(4) 0.038(19) 0.05(3) 0.017(18) 0.05(3) 0.02(2) C1 0.10(4) 0.07(3) 0.08(5) -0.01(3) 0.04(4) 0.03(3) C2 0.12(4) 0.07(3) 0.03(2) 0.01(2) -0.01(3) 0.05(3) C3 0.08(4) 0.25(12) 0.07(4) 0.00(5) -0.04(3) -0.07(5) C4 0.05(3) 0.21(6) 2.0(4) 0.78(17) -0.12(8) -0.03(3) C5 0.06(3) 0.08(3) 0.06(3) 0.00(3) -0.03(2) -0.01(3) C6 0.14(5) 0.07(3) 0.04(3) -0.02(3) 0.01(3) 0.00(3) C7 0.09(3) 0.05(2) 0.04(3) 0.03(2) -0.04(2) -0.01(2) C8 0.19(7) 0.14(6) 0.12(6) -0.12(6) 0.11(6) -0.08(6) C9 0.10(4) 0.08(3) 0.02(2) 0.03(2) 0.01(2) 0.03(3) C10 0.00(2) 0.42(16) 0.10(5) -0.12(7) 0.01(2) -0.09(5) C11 0.000(19) 0.15(5) 0.18(7) -0.08(5) 0.05(3) -0.04(3) C12 0.00(2) 0.20(8) 0.26(11) -0.16(8) -0.02(3) -0.01(3) C13 0.14(5) 0.11(5) 0.06(4) -0.02(3) -0.06(4) 0.06(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 I1 3.216(3) . ? Pb1 I1 3.220(3) 4_566 ? Pb1 I2 3.223(3) . ? Pb1 I2 3.239(3) 4_565 ? Pb1 I3 3.249(3) . ? Pb1 I3 3.307(3) 4_566 ? I1 Pb1 3.220(3) 4_565 ? I2 Pb1 3.239(3) 4_566 ? I3 Pb1 3.307(3) 4_565 ? N2 C6 1.17(7) . ? N2 N1 1.45(5) . ? N1 C5 1.36(2) . ? N1 C1 1.36(2) . ? C1 C2 1.36(2) . ? C1 H1A 0.9300 . ? C2 C3 1.36(2) . ? C2 H2B 0.9300 . ? C3 C4 1.36(2) . ? C3 H3A 0.9300 . ? C4 C5 1.36(2) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.73(7) . ? C6 H6 0.9300 . ? C7 C8 1.356(19) . ? C7 C12 1.356(19) . ? C8 C9 1.36(2) . ? C8 H8A 0.9300 . ? C9 C10 1.36(2) . ? C9 H9A 0.9300 . ? C10 C11 1.36(2) . ? C10 C13 1.45(6) . ? C11 C12 1.36(2) . ? C11 H11A 0.9300 . ? C12 H12A 0.9300 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 93.76(10) . 4_566 ? I1 Pb1 I2 92.93(9) . . ? I1 Pb1 I2 86.39(9) 4_566 . ? I1 Pb1 I2 86.19(9) . 4_565 ? I1 Pb1 I2 94.53(9) 4_566 4_565 ? I2 Pb1 I2 178.77(8) . 4_565 ? I1 Pb1 I3 85.56(10) . . ? I1 Pb1 I3 176.39(9) 4_566 . ? I2 Pb1 I3 90.11(9) . . ? I2 Pb1 I3 88.96(9) 4_565 . ? I1 Pb1 I3 177.89(9) . 4_566 ? I1 Pb1 I3 84.54(9) 4_566 4_566 ? I2 Pb1 I3 88.22(9) . 4_566 ? I2 Pb1 I3 92.68(9) 4_565 4_566 ? I3 Pb1 I3 96.21(11) . 4_566 ? Pb1 I1 Pb1 75.86(8) . 4_565 ? Pb1 I2 Pb1 75.49(8) . 4_566 ? Pb1 I3 Pb1 74.22(8) . 4_565 ? C6 N2 N1 116(5) . . ? C5 N1 C1 120.0 . . ? C5 N1 N2 121(2) . . ? C1 N1 N2 119(2) . . ? C2 C1 N1 120.0 . . ? C2 C1 H1A 120.0 . . ? N1 C1 H1A 120.0 . . ? C1 C2 C3 120.0 . . ? C1 C2 H2B 120.0 . . ? C3 C2 H2B 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3A 120.0 . . ? C2 C3 H3A 120.0 . . ? C3 C4 C5 120.0 . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? N1 C5 C4 120.0 . . ? N1 C5 H5A 120.0 . . ? C4 C5 H5A 120.0 . . ? N2 C6 C7 120(5) . . ? N2 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C8 C7 C12 120.0 . . ? C8 C7 C6 118(3) . . ? C12 C7 C6 122(3) . . ? C7 C8 C9 120.0 . . ? C7 C8 H8A 120.0 . . ? C9 C8 H8A 120.0 . . ? C8 C9 C10 120.0 . . ? C8 C9 H9A 120.0 . . ? C10 C9 H9A 120.0 . . ? C11 C10 C9 120.0 . . ? C11 C10 C13 120(4) . . ? C9 C10 C13 120(4) . . ? C10 C11 C12 120.0 . . ? C10 C11 H11A 120.0 . . ? C12 C11 H11A 120.0 . . ? C11 C12 C7 120.0 . . ? C11 C12 H12A 120.0 . . ? C7 C12 H12A 120.0 . . ? C10 C13 H13A 109.5 . . ? C10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 7.298 _refine_diff_density_min -6.711 _refine_diff_density_rms 1.004 #==================== data_pcl-780410 _database_code_depnum_ccdc_archive 'CCDC 780410' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 Cl I3 N2 Pb' _chemical_formula_weight 805.56 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' Cl Cl 0.1484 0.1585 '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 'P 21/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 13.8862(16) _cell_length_b 16.3785(19) _cell_length_c 7.8922(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.884(2) _cell_angle_gamma 90.00 _cell_volume 1794.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3338 _cell_measurement_theta_min 2.4871 _cell_measurement_theta_max 26.3912 _exptl_crystal_description neddle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.981 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1416 _exptl_absorpt_coefficient_mu 14.699 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.0299 _exptl_absorpt_correction_T_max 0.1570 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13303 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 25.50 _reflns_number_total 3330 _reflns_number_gt 2495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0323P)^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 3330 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0625 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 0.130967(18) 0.748668(15) 1.06451(3) 0.03852(10) Uani 1 1 d . . . I1 I -0.02706(3) 0.66643(3) 0.80629(6) 0.04647(14) Uani 1 1 d . . . I2 I 0.28951(3) 0.67211(3) 0.81390(6) 0.04952(14) Uani 1 1 d . . . I3 I 0.12686(3) 0.90544(3) 0.81933(5) 0.04564(14) Uani 1 1 d . . . Cl1 Cl 0.46095(19) 0.61714(15) 0.1542(3) 0.0806(7) Uani 1 1 d . . . N1 N 0.7479(4) 0.6100(3) 1.0553(7) 0.0461(15) Uani 1 1 d . . . N2 N 0.6903(5) 0.6268(4) 0.9094(8) 0.0574(17) Uani 1 1 d . . . C1 C 0.7438(6) 0.6686(4) 1.1722(10) 0.057(2) Uani 1 1 d . . . H1 H 0.7045 0.7138 1.1543 0.069 Uiso 1 1 calc R . . C2 C 0.7976(7) 0.6622(5) 1.3190(12) 0.071(3) Uani 1 1 d . . . H2 H 0.7946 0.7033 1.3999 0.086 Uiso 1 1 calc R . . C3 C 0.8547(6) 0.5969(5) 1.3471(11) 0.064(2) Uani 1 1 d . . . H3 H 0.8912 0.5926 1.4465 0.077 Uiso 1 1 calc R . . C4 C 0.8580(6) 0.5366(5) 1.2255(10) 0.064(2) Uani 1 1 d . . . H4 H 0.8955 0.4903 1.2435 0.077 Uiso 1 1 calc R . . C5 C 0.8060(6) 0.5453(5) 1.0788(10) 0.057(2) Uani 1 1 d . . . H5 H 0.8107 0.5060 0.9942 0.068 Uiso 1 1 calc R . . C6 C 0.6835(5) 0.5732(5) 0.7955(10) 0.056(2) Uani 1 1 d . . . H6 H 0.7165 0.5243 0.8107 0.067 Uiso 1 1 calc R . . C7 C 0.6264(5) 0.5842(5) 0.6417(10) 0.052(2) Uani 1 1 d . . . C8 C 0.5638(6) 0.6505(4) 0.6209(10) 0.0522(19) Uani 1 1 d . . . H8 H 0.5560 0.6877 0.7087 0.063 Uiso 1 1 calc R . . C9 C 0.5140(6) 0.6604(5) 0.4711(11) 0.062(2) Uani 1 1 d . . . H9 H 0.4725 0.7045 0.4566 0.075 Uiso 1 1 calc R . . C10 C 0.5258(5) 0.6049(5) 0.3423(10) 0.055(2) Uani 1 1 d . . . C11 C 0.5862(5) 0.5382(4) 0.3598(10) 0.052(2) Uani 1 1 d . . . H11 H 0.5924 0.5007 0.2721 0.063 Uiso 1 1 calc R . . C12 C 0.6364(5) 0.5286(5) 0.5081(10) 0.053(2) Uani 1 1 d . . . H12 H 0.6779 0.4844 0.5210 0.064 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 0.04519(17) 0.04321(17) 0.02712(15) 0.00062(11) -0.00068(11) 0.00103(12) I1 0.0436(3) 0.0508(3) 0.0451(3) -0.0026(2) 0.0030(2) -0.0075(2) I2 0.0411(3) 0.0627(3) 0.0447(3) -0.0037(2) -0.0024(2) 0.0105(2) I3 0.0598(3) 0.0370(3) 0.0401(3) 0.0012(2) -0.0003(2) -0.0071(2) Cl1 0.0830(17) 0.0867(17) 0.0714(15) 0.0201(13) -0.0195(13) 0.0038(13) N1 0.049(4) 0.037(3) 0.052(4) 0.002(3) 0.005(3) 0.000(3) N2 0.063(5) 0.048(4) 0.061(4) 0.005(3) -0.005(4) 0.011(3) C1 0.075(6) 0.040(5) 0.057(5) -0.003(4) 0.020(5) -0.005(4) C2 0.087(7) 0.057(6) 0.071(6) -0.019(5) 0.013(5) -0.018(5) C3 0.061(6) 0.070(6) 0.060(5) -0.002(5) -0.004(4) -0.010(5) C4 0.076(6) 0.063(6) 0.054(5) 0.002(4) -0.003(5) 0.016(5) C5 0.068(6) 0.049(5) 0.053(5) -0.011(4) -0.003(4) 0.011(4) C6 0.051(5) 0.054(5) 0.063(5) -0.002(4) -0.003(4) 0.011(4) C7 0.047(5) 0.056(5) 0.053(5) 0.011(4) 0.005(4) -0.003(4) C8 0.052(5) 0.040(4) 0.064(5) -0.001(4) 0.002(4) 0.005(4) C9 0.063(6) 0.051(5) 0.073(6) 0.007(4) 0.000(5) 0.007(4) C10 0.046(5) 0.058(5) 0.062(5) 0.020(4) 0.000(4) -0.001(4) C11 0.050(5) 0.048(5) 0.059(5) -0.003(4) 0.008(4) 0.005(4) C12 0.042(5) 0.055(5) 0.062(5) -0.001(4) -0.001(4) 0.007(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 I2 3.2047(6) 4_576 ? Pb1 I3 3.2152(6) . ? Pb1 I3 3.2284(6) 4_576 ? Pb1 I2 3.2350(6) . ? Pb1 I1 3.2434(6) 4_576 ? Pb1 I1 3.2627(6) . ? I1 Pb1 3.2434(6) 4_575 ? I2 Pb1 3.2047(6) 4_575 ? I3 Pb1 3.2284(6) 4_575 ? Cl1 C10 1.736(8) . ? N1 C1 1.333(8) . ? N1 C5 1.343(9) . ? N1 N2 1.419(8) . ? N2 C6 1.259(9) . ? C1 C2 1.373(12) . ? C2 C3 1.347(11) . ? C3 C4 1.378(10) . ? C4 C5 1.363(10) . ? C6 C7 1.451(10) . ? C7 C8 1.398(10) . ? C7 C12 1.402(10) . ? C8 C9 1.370(11) . ? C9 C10 1.376(11) . ? C10 C11 1.383(10) . ? C11 C12 1.362(9) . ? 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 I3 92.974(15) 4_576 . ? I2 Pb1 I3 87.280(15) 4_576 4_576 ? I3 Pb1 I3 177.436(17) . 4_576 ? I2 Pb1 I2 93.723(18) 4_576 . ? I3 Pb1 I2 86.992(15) . . ? I3 Pb1 I2 95.540(15) 4_576 . ? I2 Pb1 I1 85.968(16) 4_576 4_576 ? I3 Pb1 I1 90.331(15) . 4_576 ? I3 Pb1 I1 87.141(14) 4_576 4_576 ? I2 Pb1 I1 177.286(14) . 4_576 ? I2 Pb1 I1 178.877(15) 4_576 . ? I3 Pb1 I1 87.036(15) . . ? I3 Pb1 I1 92.760(15) 4_576 . ? I2 Pb1 I1 85.156(16) . . ? I1 Pb1 I1 95.155(18) 4_576 . ? Pb1 I1 Pb1 74.683(13) 4_575 . ? Pb1 I2 Pb1 75.584(14) 4_575 . ? Pb1 I3 Pb1 75.533(13) . 4_575 ? C1 N1 C5 120.3(7) . . ? C1 N1 N2 113.1(6) . . ? C5 N1 N2 126.6(6) . . ? C6 N2 N1 118.6(6) . . ? N1 C1 C2 120.0(8) . . ? C3 C2 C1 120.7(8) . . ? C2 C3 C4 118.6(9) . . ? C5 C4 C3 119.6(8) . . ? N1 C5 C4 120.6(7) . . ? N2 C6 C7 123.0(7) . . ? C8 C7 C12 119.0(7) . . ? C8 C7 C6 121.7(7) . . ? C12 C7 C6 119.3(7) . . ? C9 C8 C7 119.9(8) . . ? C8 C9 C10 119.6(8) . . ? C9 C10 C11 121.9(8) . . ? C9 C10 Cl1 119.3(6) . . ? C11 C10 Cl1 118.8(7) . . ? C12 C11 C10 118.6(7) . . ? C11 C12 C7 121.1(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.781 _refine_diff_density_min -0.660 _refine_diff_density_rms 0.151 #========== data_pf-780411 _database_code_depnum_ccdc_archive 'CCDC 780411' #TrackingRef 'cifs-of-1-8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 F I3 N2 Pb' _chemical_formula_weight 789.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 13.693(2) _cell_length_b 22.527(4) _cell_length_c 15.988(3) _cell_angle_alpha 90.00 _cell_angle_beta 126.139(16) _cell_angle_gamma 90.00 _cell_volume 3982.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2339 _cell_measurement_theta_min 2.7036 _cell_measurement_theta_max 26.8752 _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2768 _exptl_absorpt_coefficient_mu 13.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.1105 _exptl_absorpt_correction_T_max 0.3537 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _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 'Smart CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11043 _diffrn_reflns_av_R_equivalents 0.2221 _diffrn_reflns_av_sigmaI/netI 0.1499 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3876 _reflns_number_gt 2384 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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. During the refinement, the disorder solvent molecules were removed and Platon SQUEEZE was used for smoothing the electron density; the details from the Platon SQUEEZE run in a sqf file were appended to the cif. ; _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^)+(0.0736P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00050(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3876 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0826 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1657 _refine_ls_wR_factor_gt 0.1561 _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_restrained_S_all 0.862 _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 0.5000 0.5000 0.0000 0.0419(3) Uani 1 2 d S . . Pb2 Pb 0.5000 0.50649(3) 0.2500 0.0400(3) Uani 1 2 d S . . I1 I 0.39093(8) 0.60358(4) 0.06356(7) 0.0514(3) Uani 1 1 d . . . I2 I 0.38493(9) 0.40750(4) 0.07059(7) 0.0550(3) Uani 1 1 d . . . I3 I 0.72940(9) 0.50191(4) 0.24460(9) 0.0610(3) Uani 1 1 d . . . N1 N 0.4615(10) 0.2091(5) 0.0634(7) 0.049(3) Uani 1 1 d . . . N2 N 0.4103(10) 0.2349(5) 0.1097(8) 0.060(3) Uani 1 1 d . . . F1 F 0.1504(8) 0.2866(5) 0.3226(7) 0.093(3) Uani 1 1 d . . . C1 C 0.4840(15) 0.1502(6) 0.0675(11) 0.075(5) Uani 1 1 d . . . H1 H 0.4608 0.1235 0.0972 0.090 Uiso 1 1 calc R . . C2 C 0.5425(17) 0.1316(7) 0.0258(12) 0.085(5) Uani 1 1 d . . . H2 H 0.5607 0.0915 0.0292 0.103 Uiso 1 1 calc R . . C3 C 0.5746(13) 0.1693(6) -0.0200(10) 0.058(4) Uani 1 1 d . . . H3 H 0.6111 0.1552 -0.0502 0.069 Uiso 1 1 calc R . . C4 C 0.5519(12) 0.2292(6) -0.0209(10) 0.052(3) Uani 1 1 d . . . H4 H 0.5744 0.2563 -0.0505 0.062 Uiso 1 1 calc R . . C5 C 0.4957(10) 0.2480(6) 0.0224(9) 0.047(3) Uani 1 1 d . . . H5 H 0.4813 0.2883 0.0232 0.056 Uiso 1 1 calc R . . C6 C 0.3503(11) 0.2020(6) 0.1279(9) 0.046(3) Uani 1 1 d . . . H6 H 0.3402 0.1621 0.1096 0.055 Uiso 1 1 calc R . . C7 C 0.2959(7) 0.2255(3) 0.1776(6) 0.042(3) Uani 1 1 d G . . C8 C 0.3048(7) 0.2844(3) 0.2027(7) 0.052(3) Uani 1 1 d G . . H8 H 0.3439 0.3106 0.1866 0.063 Uiso 1 1 calc R . . C9 C 0.2561(8) 0.3047(3) 0.2516(7) 0.057(4) Uani 1 1 d G . . H9 H 0.2622 0.3446 0.2686 0.068 Uiso 1 1 calc R . . C10 C 0.1985(8) 0.2660(4) 0.2754(6) 0.053(3) Uani 1 1 d G . . C11 C 0.1896(8) 0.2071(4) 0.2503(7) 0.067(4) Uani 1 1 d G . . H11 H 0.1505 0.1809 0.2664 0.081 Uiso 1 1 calc R . . C12 C 0.2383(8) 0.1869(3) 0.2014(7) 0.055(3) Uani 1 1 d G . . H12 H 0.2322 0.1469 0.1844 0.067 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 0.0562(5) 0.0344(4) 0.0558(5) 0.0002(3) 0.0444(4) -0.0015(3) Pb2 0.0496(5) 0.0356(4) 0.0507(5) 0.000 0.0384(4) 0.000 I1 0.0639(6) 0.0347(4) 0.0684(6) 0.0054(4) 0.0460(6) 0.0104(4) I2 0.0813(7) 0.0376(5) 0.0655(6) -0.0086(4) 0.0540(6) -0.0203(4) I3 0.0494(6) 0.0688(7) 0.0822(8) 0.0008(5) 0.0484(6) 0.0002(4) N1 0.054(7) 0.048(6) 0.038(6) 0.000(5) 0.023(6) 0.007(5) N2 0.084(9) 0.041(6) 0.072(8) 0.002(5) 0.056(7) 0.004(6) F1 0.091(7) 0.110(8) 0.111(7) -0.014(6) 0.078(6) -0.002(6) C1 0.127(15) 0.047(8) 0.082(11) 0.012(8) 0.079(12) 0.016(9) C2 0.147(15) 0.038(8) 0.107(13) 0.006(8) 0.095(13) 0.026(10) C3 0.060(9) 0.068(10) 0.049(8) 0.003(7) 0.034(8) 0.021(8) C4 0.052(9) 0.046(8) 0.055(8) 0.002(6) 0.030(8) -0.005(6) C5 0.043(8) 0.034(6) 0.047(8) -0.002(6) 0.018(7) -0.003(5) C6 0.048(7) 0.043(7) 0.049(8) 0.002(6) 0.029(7) 0.001(6) C7 0.027(6) 0.040(7) 0.051(8) 0.004(6) 0.019(6) -0.005(5) C8 0.063(9) 0.037(7) 0.067(9) 0.008(6) 0.044(8) -0.001(6) C9 0.063(9) 0.045(7) 0.075(10) -0.010(7) 0.048(9) -0.001(7) C10 0.048(8) 0.069(9) 0.044(8) 0.000(7) 0.028(7) 0.003(7) C11 0.059(10) 0.068(10) 0.069(10) 0.016(8) 0.035(9) -0.009(8) C12 0.051(9) 0.048(8) 0.062(9) 0.007(6) 0.030(8) -0.007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 I2 3.1931(8) 5_665 ? Pb1 I2 3.1931(8) . ? Pb1 I1 3.2400(9) . ? Pb1 I1 3.2400(9) 5_665 ? Pb1 I3 3.2670(15) 5_665 ? Pb1 I3 3.2670(15) . ? Pb2 I3 3.1945(11) . ? Pb2 I3 3.1945(11) 2_655 ? Pb2 I2 3.2174(10) . ? Pb2 I2 3.2174(10) 2_655 ? Pb2 I1 3.2631(10) 2_655 ? Pb2 I1 3.2631(10) . ? N1 C5 1.333(16) . ? N1 C1 1.356(16) . ? N1 N2 1.408(14) . ? N2 C6 1.262(14) . ? F1 C10 1.343(11) . ? C1 C2 1.376(19) . ? C1 H1 0.9300 . ? C2 C3 1.352(19) . ? C2 H2 0.9300 . ? C3 C4 1.383(18) . ? C3 H3 0.9300 . ? C4 C5 1.372(18) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 C7 1.471(14) . ? C6 H6 0.9300 . ? C7 C8 1.371(5) . ? C7 C12 1.371(5) . ? C8 C9 1.371(5) . ? C8 H8 0.9300 . ? C9 C10 1.371(5) . ? C9 H9 0.9300 . ? C10 C11 1.371(5) . ? C11 C12 1.371(5) . ? C11 H11 0.9300 . ? C12 H12 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag I2 Pb1 I2 180.0 5_665 . ? I2 Pb1 I1 93.20(3) 5_665 . ? I2 Pb1 I1 86.80(3) . . ? I2 Pb1 I1 86.80(3) 5_665 5_665 ? I2 Pb1 I1 93.20(3) . 5_665 ? I1 Pb1 I1 180.0 . 5_665 ? I2 Pb1 I3 84.95(3) 5_665 5_665 ? I2 Pb1 I3 95.05(3) . 5_665 ? I1 Pb1 I3 95.12(3) . 5_665 ? I1 Pb1 I3 84.88(3) 5_665 5_665 ? I2 Pb1 I3 95.05(3) 5_665 . ? I2 Pb1 I3 84.95(3) . . ? I1 Pb1 I3 84.88(3) . . ? I1 Pb1 I3 95.12(3) 5_665 . ? I3 Pb1 I3 180.0 5_665 . ? I3 Pb2 I3 176.30(4) . 2_655 ? I3 Pb2 I2 85.75(3) . . ? I3 Pb2 I2 91.68(3) 2_655 . ? I3 Pb2 I2 91.68(3) . 2_655 ? I3 Pb2 I2 85.75(3) 2_655 2_655 ? I2 Pb2 I2 92.26(4) . 2_655 ? I3 Pb2 I1 96.82(3) . 2_655 ? I3 Pb2 I1 85.68(3) 2_655 2_655 ? I2 Pb2 I1 176.94(2) . 2_655 ? I2 Pb2 I1 86.01(3) 2_655 2_655 ? I3 Pb2 I1 85.68(3) . . ? I3 Pb2 I1 96.82(3) 2_655 . ? I2 Pb2 I1 86.01(3) . . ? I2 Pb2 I1 176.94(2) 2_655 . ? I1 Pb2 I1 95.83(4) 2_655 . ? Pb1 I1 Pb2 75.91(2) . . ? Pb1 I2 Pb2 77.21(2) . . ? Pb2 I3 Pb1 76.48(3) . . ? C5 N1 C1 122.0(12) . . ? C5 N1 N2 114.5(11) . . ? C1 N1 N2 123.2(11) . . ? C6 N2 N1 118.2(11) . . ? N1 C1 C2 117.1(14) . . ? N1 C1 H1 121.4 . . ? C2 C1 H1 121.4 . . ? C3 C2 C1 122.7(14) . . ? C3 C2 H2 118.7 . . ? C1 C2 H2 118.7 . . ? C2 C3 C4 118.3(13) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C5 C4 C3 119.1(12) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? N1 C5 C4 120.7(12) . . ? N1 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? N2 C6 C7 121.3(11) . . ? N2 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? C8 C7 C12 120.0 . . ? C8 C7 C6 121.4(7) . . ? C12 C7 C6 118.6(7) . . ? C7 C8 C9 120.0 . . ? C7 C8 H8 120.0 . . ? C9 C8 H8 120.0 . . ? C8 C9 C10 120.0 . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? F1 C10 C9 119.4(7) . . ? F1 C10 C11 120.6(7) . . ? C9 C10 C11 120.0 . . ? C12 C11 C10 120.0 . . ? C12 C11 H11 120.0 . . ? C10 C11 H11 120.0 . . ? C7 C12 C11 120.0 . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag I2 Pb1 I1 Pb2 -137.89(3) 5_665 . . . ? I2 Pb1 I1 Pb2 42.11(3) . . . . ? I1 Pb1 I1 Pb2 11(100) 5_665 . . . ? I3 Pb1 I1 Pb2 136.90(2) 5_665 . . . ? I3 Pb1 I1 Pb2 -43.10(2) . . . . ? I3 Pb2 I1 Pb1 44.26(2) . . . . ? I3 Pb2 I1 Pb1 -132.99(3) 2_655 . . . ? I2 Pb2 I1 Pb1 -41.77(2) . . . . ? I2 Pb2 I1 Pb1 13.9(4) 2_655 . . . ? I1 Pb2 I1 Pb1 140.69(3) 2_655 . . . ? I2 Pb1 I2 Pb2 72(100) 5_665 . . . ? I1 Pb1 I2 Pb2 -42.57(3) . . . . ? I1 Pb1 I2 Pb2 137.43(3) 5_665 . . . ? I3 Pb1 I2 Pb2 -137.43(2) 5_665 . . . ? I3 Pb1 I2 Pb2 42.57(2) . . . . ? I3 Pb2 I2 Pb1 -43.71(2) . . . . ? I3 Pb2 I2 Pb1 138.96(3) 2_655 . . . ? I2 Pb2 I2 Pb1 -135.23(3) 2_655 . . . ? I1 Pb2 I2 Pb1 169.3(4) 2_655 . . . ? I1 Pb2 I2 Pb1 42.24(2) . . . . ? I3 Pb2 I3 Pb1 88.779(12) 2_655 . . . ? I2 Pb2 I3 Pb1 42.64(2) . . . . ? I2 Pb2 I3 Pb1 134.78(2) 2_655 . . . ? I1 Pb2 I3 Pb1 -139.04(2) 2_655 . . . ? I1 Pb2 I3 Pb1 -43.67(2) . . . . ? I2 Pb1 I3 Pb2 136.89(2) 5_665 . . . ? I2 Pb1 I3 Pb2 -43.11(2) . . . . ? I1 Pb1 I3 Pb2 44.13(2) . . . . ? I1 Pb1 I3 Pb2 -135.87(2) 5_665 . . . ? I3 Pb1 I3 Pb2 -31.03(4) 5_665 . . . ? C5 N1 N2 C6 163.5(11) . . . . ? C1 N1 N2 C6 -21.9(19) . . . . ? C5 N1 C1 C2 -1(2) . . . . ? N2 N1 C1 C2 -175.2(14) . . . . ? N1 C1 C2 C3 -2(3) . . . . ? C1 C2 C3 C4 3(3) . . . . ? C2 C3 C4 C5 -1(2) . . . . ? C1 N1 C5 C4 2.3(19) . . . . ? N2 N1 C5 C4 177.0(11) . . . . ? C3 C4 C5 N1 -1(2) . . . . ? N1 N2 C6 C7 178.9(10) . . . . ? N2 C6 C7 C8 2.3(15) . . . . ? N2 C6 C7 C12 -175.9(10) . . . . ? C12 C7 C8 C9 0.0 . . . . ? C6 C7 C8 C9 -178.2(9) . . . . ? C7 C8 C9 C10 0.0 . . . . ? C8 C9 C10 F1 -179.5(9) . . . . ? C8 C9 C10 C11 0.0 . . . . ? F1 C10 C11 C12 179.5(9) . . . . ? C9 C10 C11 C12 0.0 . . . . ? C8 C7 C12 C11 0.0 . . . . ? C6 C7 C12 C11 178.2(9) . . . . ? C10 C11 C12 C7 0.0 . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 2.572 _refine_diff_density_min -3.100 _refine_diff_density_rms 0.328 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.000 0.483 0.250 145.2 47.8 2 0.000 0.517 0.750 145.2 45.8 3 0.500 0.017 0.750 145.2 45.8 4 0.500 0.983 1.250 145.2 47.8 _platon_squeeze_details ; ? ; #=======