Supplementary material (ESI) for CrystEngComm This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Zhi Rong Chen' _publ_contact_author_address ; College of Chemistry and Chemical Engineering Fuzhou University Fuzhou 350108 CHINA ; _publ_contact_author_email ZRCHEN@FZU.EDU.CN _publ_section_title ; A Series of Lead(II)/Iodine Hybrid Materials Based on 1- and 2-D Metal-Organic Motifs Linked by Different Organic Conjugated Ligands ; loop_ _publ_author_name 'Zhi Rong Chen' 'Miao Feng' 'Chang-Cang Huang' 'Xi He Huang' ; HaoHong Li ; 'Yun Lin' 'YunJie Wang' data_y08f _database_code_depnum_ccdc_archive 'CCDC 634298' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H4 I2 N O Pb' _chemical_formula_sum 'C5 H4 I2 N O Pb' _chemical_formula_weight 555.09 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.5644(9) _cell_length_b 8.9738(18) _cell_length_c 11.778(2) _cell_angle_alpha 78.05(3) _cell_angle_beta 83.67(3) _cell_angle_gamma 84.67(3) _cell_volume 467.88(16) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description Block _exptl_crystal_colour Blown _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.940 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 474.0 _exptl_absorpt_coefficient_mu 24.567 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.013 _exptl_absorpt_correction_T_max 0.052 _exptl_absorpt_process_details 'TEXRAY software (Molecular Structure Corporation, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotor target' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Weissenberg IP' _diffrn_measurement_method 'scintillation counter' _diffrn_detector_area_resol_mean None _diffrn_standards_number None _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 4670 _diffrn_reflns_av_R_equivalents 0.0780 _diffrn_reflns_av_sigmaI/netI 0.1128 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.20 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2140 _reflns_number_gt 1510 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'TEXRAY software (Molecular Structure Corporation, 1999)' _computing_cell_refinement 'TEXRAY software' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material "SHELXL-97/2 (Sheldrick,1997)')" _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^)+(0.0000P)^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 ref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2140 _refine_ls_number_parameters 93 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1108 _refine_ls_wR_factor_gt 0.0997 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 0.30452(8) 0.91374(5) 0.35680(4) 0.04399(19) Uani 1 1 d . . . I1 I 0.22646(16) 1.24247(10) 0.45986(7) 0.0513(3) Uani 1 1 d . . . I2 I -0.17756(15) 1.03626(10) 0.17402(7) 0.0499(3) Uani 1 1 d . . . N1 N 0.5211(19) 0.6420(11) 0.2119(9) 0.043(3) Uani 1 1 d . . . O1 O 0.331(2) 0.6819(12) 0.2918(9) 0.066(3) Uani 1 1 d . . . C1 C 0.505(3) 0.7035(14) 0.0998(11) 0.048(3) Uani 1 1 d . . . H1 H 0.3678 0.7848 0.0782 0.057 Uiso 1 1 calc R . . C2 C 0.686(3) 0.6496(14) 0.0173(11) 0.047(3) Uani 1 1 d . . . H2 H 0.6663 0.6929 -0.0606 0.057 Uiso 1 1 calc R . . C3 C 0.902(2) 0.5315(12) 0.0442(11) 0.038(3) Uani 1 1 d . . . C4 C 0.915(3) 0.4791(14) 0.1635(12) 0.049(3) Uani 1 1 d . . . H4 H 1.0594 0.4030 0.1882 0.059 Uiso 1 1 calc R . . C5 C 0.731(3) 0.5319(16) 0.2438(12) 0.054(4) Uani 1 1 d . . . H5 H 0.7486 0.4922 0.3225 0.065 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 0.0350(3) 0.0522(3) 0.0421(3) -0.0016(2) -0.0046(2) -0.00580(18) I1 0.0433(4) 0.0562(6) 0.0468(5) 0.0093(4) -0.0072(4) -0.0048(3) I2 0.0379(4) 0.0618(6) 0.0423(5) 0.0089(4) -0.0050(3) -0.0053(3) N1 0.037(5) 0.047(6) 0.046(6) -0.011(5) -0.004(5) -0.010(4) O1 0.069(6) 0.060(7) 0.071(7) -0.030(5) 0.015(5) -0.009(5) C1 0.049(7) 0.045(8) 0.042(8) 0.003(6) -0.006(6) 0.006(5) C2 0.058(7) 0.045(8) 0.037(7) 0.007(6) -0.015(6) -0.010(6) C3 0.043(6) 0.017(5) 0.057(8) -0.005(5) -0.016(5) -0.005(4) C4 0.056(7) 0.040(7) 0.050(8) 0.000(6) -0.013(7) -0.003(5) C5 0.044(7) 0.068(9) 0.045(8) 0.014(7) -0.016(6) -0.015(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 O1 2.350(11) . ? Pb1 I2 3.1324(14) 1_655 ? Pb1 I2 3.2094(12) . ? Pb1 I1 3.2279(13) 2_676 ? Pb1 I1 3.2749(14) 2_576 ? Pb1 I1 3.3905(14) . ? I1 Pb1 3.2279(13) 2_676 ? I1 Pb1 3.2749(14) 2_576 ? I2 Pb1 3.1324(14) 1_455 ? N1 O1 1.291(15) . ? N1 C1 1.329(14) . ? N1 C5 1.336(16) . ? C1 C2 1.34(2) . ? C1 H1 0.9300 . ? C2 C3 1.389(16) . ? C2 H2 0.9300 . ? C3 C4 1.392(17) . ? C3 C3 1.47(3) 2_765 ? C4 C5 1.33(2) . ? C4 H4 0.9300 . ? C5 H5 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 O1 Pb1 I2 92.1(3) . 1_655 ? O1 Pb1 I2 86.6(2) . . ? I2 Pb1 I2 92.06(3) 1_655 . ? O1 Pb1 I1 88.3(2) . 2_676 ? I2 Pb1 I1 90.27(3) 1_655 2_676 ? I2 Pb1 I1 174.45(3) . 2_676 ? O1 Pb1 I1 82.9(2) . 2_576 ? I2 Pb1 I1 175.03(3) 1_655 2_576 ? I2 Pb1 I1 88.09(3) . 2_576 ? I1 Pb1 I1 89.16(3) 2_676 2_576 ? O1 Pb1 I1 176.5(2) . . ? I2 Pb1 I1 91.29(4) 1_655 . ? I2 Pb1 I1 92.50(3) . . ? I1 Pb1 I1 92.48(3) 2_676 . ? I1 Pb1 I1 93.67(3) 2_576 . ? Pb1 I1 Pb1 89.16(3) 2_676 2_576 ? Pb1 I1 Pb1 87.52(3) 2_676 . ? Pb1 I1 Pb1 86.33(3) 2_576 . ? Pb1 I2 Pb1 92.06(3) 1_455 . ? O1 N1 C1 121.7(11) . . ? O1 N1 C5 118.5(11) . . ? C1 N1 C5 119.8(12) . . ? N1 O1 Pb1 125.7(7) . . ? N1 C1 C2 120.8(11) . . ? N1 C1 H1 119.6 . . ? C2 C1 H1 119.6 . . ? C1 C2 C3 122.2(11) . . ? C1 C2 H2 118.9 . . ? C3 C2 H2 118.9 . . ? C2 C3 C4 113.4(12) . . ? C2 C3 C3 123.3(13) . 2_765 ? C4 C3 C3 123.3(12) . 2_765 ? C5 C4 C3 123.5(12) . . ? C5 C4 H4 118.2 . . ? C3 C4 H4 118.2 . . ? C4 C5 N1 120.1(11) . . ? C4 C5 H5 120.0 . . ? N1 C5 H5 120.0 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.447 _refine_diff_density_min -1.900 _refine_diff_density_rms 0.299 data_1 _database_code_depnum_ccdc_archive 'CCDC 656622' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H8 I2 N2 O2 Pb' _chemical_formula_sum 'C10 H8 I2 N2 O2 Pb' _chemical_formula_weight 649.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' O O 0.0106 0.0060 '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 C2/c _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.866(4) _cell_length_b 8.6033(17) _cell_length_c 9.6102(19) _cell_angle_alpha 90.00 _cell_angle_beta 115.43(3) _cell_angle_gamma 90.00 _cell_volume 1408.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 18 _cell_measurement_theta_min 12 _cell_measurement_theta_max 15 _exptl_crystal_description Block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.061 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 16.351 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.054 _exptl_absorpt_correction_T_max 0.141 _exptl_absorpt_process_details 'TEXRAY software (Molecular Structure Corporation, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotor target' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Weissenberg IP' _diffrn_measurement_method 'scintillation counter' _diffrn_detector_area_resol_mean None _diffrn_standards_number None _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 6759 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0426 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1629 _reflns_number_gt 1495 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'TEXRAY software (Molecular Structure Corporation, 1999)' _computing_cell_refinement 'TEXRAY software' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material "SHELXL-97/2 (Sheldrick,1997)')" _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+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 0.0010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1629 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0308 _refine_ls_wR_factor_ref 0.0655 _refine_ls_wR_factor_gt 0.0641 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _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 0.42769(4) 0.2500 0.03335(13) Uani 1 2 d S . . I1 I -0.12045(3) 0.60635(5) 0.39394(4) 0.04324(15) Uani 1 1 d . . . O1 O 0.0583(3) 0.2083(5) 0.1924(4) 0.0382(10) Uani 1 1 d . . . N1 N 0.0892(3) 0.0966(5) 0.2943(5) 0.0309(10) Uani 1 1 d . . . C1 C 0.1665(4) 0.0939(7) 0.3799(7) 0.0403(14) Uani 1 1 d . . . H1 H 0.1976 0.1730 0.3699 0.048 Uiso 1 1 calc R . . C2 C 0.2011(4) -0.0259(9) 0.4840(7) 0.0453(16) Uani 1 1 d . . . H2 H 0.2550 -0.0272 0.5441 0.054 Uiso 1 1 calc R . . C3 C 0.1549(4) -0.1416(8) 0.4969(7) 0.0416(15) Uani 1 1 d . . . H3 H 0.1773 -0.2220 0.5669 0.050 Uiso 1 1 calc R . . C4 C 0.0751(4) -0.1395(7) 0.4063(6) 0.0368(14) Uani 1 1 d . . . H4 H 0.0438 -0.2186 0.4156 0.044 Uiso 1 1 calc R . . C5 C 0.0414(3) -0.0210(7) 0.3021(6) 0.0309(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Pb1 0.0303(2) 0.03680(19) 0.03370(18) 0.000 0.01449(14) 0.000 I1 0.0290(3) 0.0603(3) 0.0367(2) -0.00470(17) 0.01062(18) 0.00032(17) O1 0.043(3) 0.043(2) 0.035(2) 0.0092(17) 0.0224(19) 0.0109(19) N1 0.024(3) 0.042(3) 0.029(2) 0.0034(19) 0.013(2) 0.0013(19) C1 0.029(4) 0.048(3) 0.045(3) -0.004(3) 0.017(3) -0.006(3) C2 0.030(4) 0.067(4) 0.038(3) 0.001(3) 0.013(3) 0.008(3) C3 0.038(4) 0.052(4) 0.033(3) 0.009(3) 0.014(3) 0.013(3) C4 0.047(4) 0.036(3) 0.030(3) 0.002(2) 0.019(3) 0.001(3) C5 0.026(3) 0.039(3) 0.027(2) 0.000(2) 0.011(2) 0.002(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 O1 2.366(4) . ? Pb1 O1 2.366(4) 2 ? Pb1 I1 3.2063(13) 6_565 ? Pb1 I1 3.2063(13) 5_566 ? Pb1 I1 3.4841(8) 2 ? Pb1 I1 3.4841(8) . ? I1 Pb1 3.2063(13) 5_566 ? O1 N1 1.317(6) . ? N1 C1 1.332(8) . ? N1 C5 1.379(7) . ? C1 C2 1.389(9) . ? C1 H1 0.9300 . ? C2 C3 1.362(10) . ? C2 H2 0.9300 . ? C3 C4 1.379(9) . ? C3 H3 0.9300 . ? C4 C5 1.378(8) . ? C4 H4 0.9300 . ? C5 C5 1.448(11) 2 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Pb1 O1 74.2(2) . 2 ? O1 Pb1 I1 82.23(10) . 6_565 ? O1 Pb1 I1 89.40(10) 2 6_565 ? O1 Pb1 I1 89.40(10) . 5_566 ? O1 Pb1 I1 82.23(10) 2 5_566 ? I1 Pb1 I1 169.52(2) 6_565 5_566 ? O1 Pb1 I1 79.12(10) . 2 ? O1 Pb1 I1 153.18(10) 2 2 ? I1 Pb1 I1 84.30(2) 6_565 2 ? I1 Pb1 I1 100.36(2) 5_566 2 ? O1 Pb1 I1 153.18(10) . . ? O1 Pb1 I1 79.12(10) 2 . ? I1 Pb1 I1 100.36(2) 6_565 . ? I1 Pb1 I1 84.30(2) 5_566 . ? I1 Pb1 I1 127.64(2) 2 . ? Pb1 I1 Pb1 95.70(2) 5_566 . ? N1 O1 Pb1 120.7(3) . . ? O1 N1 C1 119.3(5) . . ? O1 N1 C5 119.0(5) . . ? C1 N1 C5 121.5(5) . . ? N1 C1 C2 120.6(6) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 119.1(7) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.1(6) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C5 C4 C3 120.4(6) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 N1 118.3(5) . . ? C4 C5 C5 121.8(5) . 2 ? N1 C5 C5 119.9(4) . 2 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.881 _refine_diff_density_min -0.979 _refine_diff_density_rms 0.170 data_1 _database_code_depnum_ccdc_archive 'CCDC 659647' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 I N O Pb, C3 H7 N O' _chemical_formula_sum 'C12 H13 I N2 O2 Pb' _chemical_formula_weight 551.34 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 P21/c _symmetry_space_group_name_Hall -P2ybc 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 16.872(5) _cell_length_b 7.2993(17) _cell_length_c 12.074(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.850(4) _cell_angle_gamma 90.00 _cell_volume 1415.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12 _cell_measurement_theta_max 18 _exptl_crystal_description Block _exptl_crystal_colour Red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000.0 _exptl_absorpt_coefficient_mu 14.096 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.14 _exptl_absorpt_correction_T_max 0.250 _exptl_absorpt_process_details 'TEXRAY software (Molecular Structure Corporation, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature -120.00 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotor target' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Weissenberg IP' _diffrn_measurement_method 'scintillation counter' _diffrn_detector_area_resol_mean None _diffrn_standards_number None _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 10536 _diffrn_reflns_av_R_equivalents 0.0430 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3253 _reflns_number_gt 2863 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'TEXRAY software (Molecular Structure Corporation, 1999)' _computing_cell_refinement 'TEXRAY software' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material "SHELXL-97/2 (Sheldrick,1997)')" _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0369P)^2^+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 0.0010(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3253 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0331 _refine_ls_wR_factor_ref 0.0760 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.008897(13) 0.70046(3) 0.613069(18) 0.02558(9) Uani 1 1 d . . . I1 I -0.09276(2) 1.07724(5) 0.58435(3) 0.03137(11) Uani 1 1 d . . . O1 O -0.0787(2) 0.5859(5) 0.4424(3) 0.0281(9) Uani 1 1 d . . . N1 N -0.1217(3) 0.5871(6) 0.6418(4) 0.0234(10) Uani 1 1 d . . . N2 N -0.4173(4) 0.8660(9) 0.4382(6) 0.0509(16) Uani 1 1 d . . . O2 O -0.5382(4) 0.7179(11) 0.4088(8) 0.107(3) Uani 1 1 d . . . C1 C -0.1408(4) 0.5810(8) 0.7395(5) 0.0327(14) Uani 1 1 d . . . H1 H -0.1014 0.6198 0.8078 0.039 Uiso 1 1 calc R . . C2 C -0.2183(4) 0.5181(10) 0.7447(6) 0.0414(16) Uani 1 1 d . . . H2 H -0.2294 0.5127 0.8154 0.050 Uiso 1 1 calc R . . C3 C -0.2767(4) 0.4653(9) 0.6451(6) 0.0364(15) Uani 1 1 d . . . H3 H -0.3282 0.4233 0.6475 0.044 Uiso 1 1 calc R . . C4 C -0.2596(4) 0.4740(8) 0.5381(5) 0.0302(13) Uani 1 1 d . . . C5 C -0.3173(4) 0.4253(9) 0.4303(6) 0.0380(15) Uani 1 1 d . . . H5 H -0.3706 0.3870 0.4269 0.046 Uiso 1 1 calc R . . C6 C -0.2953(4) 0.4343(9) 0.3322(6) 0.0389(16) Uani 1 1 d . . . H6 H -0.3341 0.4030 0.2616 0.047 Uiso 1 1 calc R . . C7 C -0.2152(4) 0.4899(8) 0.3337(5) 0.0330(14) Uani 1 1 d . . . H7 H -0.2016 0.4932 0.2647 0.040 Uiso 1 1 calc R . . C8 C -0.1564(3) 0.5395(7) 0.4367(5) 0.0264(12) Uani 1 1 d . . . C9 C -0.1794(3) 0.5354(7) 0.5414(5) 0.0254(12) Uani 1 1 d . . . C10 C -0.4705(6) 0.7677(14) 0.4698(9) 0.072(3) Uani 1 1 d . . . H10 H -0.4551 0.7317 0.5474 0.086 Uiso 1 1 calc R . . C11 C -0.3363(5) 0.9185(12) 0.5133(9) 0.076(3) Uani 1 1 d . . . H11A H -0.3079 0.9887 0.4698 0.114 Uiso 1 1 calc R . . H11B H -0.3045 0.8106 0.5437 0.114 Uiso 1 1 calc R . . H11C H -0.3425 0.9911 0.5764 0.114 Uiso 1 1 calc R . . C12 C -0.4367(7) 0.921(2) 0.3164(9) 0.111(5) Uani 1 1 d . . . H12A H -0.3911 0.9899 0.3060 0.167 Uiso 1 1 calc R . . H12B H -0.4862 0.9946 0.2949 0.167 Uiso 1 1 calc R . . H12C H -0.4457 0.8133 0.2681 0.167 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 0.02948(13) 0.01923(12) 0.02726(15) -0.00102(8) 0.00757(10) -0.00095(8) I1 0.0372(2) 0.0233(2) 0.0354(2) 0.00263(16) 0.01378(17) 0.00501(16) O1 0.033(2) 0.025(2) 0.027(2) -0.0003(17) 0.0093(17) 0.0012(17) N1 0.028(2) 0.020(2) 0.024(3) -0.0036(19) 0.010(2) 0.0013(19) N2 0.043(3) 0.049(4) 0.055(4) 0.001(3) 0.008(3) -0.007(3) O2 0.048(4) 0.129(7) 0.139(8) 0.003(5) 0.023(4) -0.034(4) C1 0.034(3) 0.031(3) 0.031(3) 0.003(3) 0.007(3) 0.003(3) C2 0.046(4) 0.046(4) 0.040(4) 0.001(3) 0.023(3) -0.001(3) C3 0.033(3) 0.033(3) 0.046(4) 0.002(3) 0.016(3) -0.005(3) C4 0.032(3) 0.021(3) 0.038(4) 0.000(3) 0.010(3) 0.001(2) C5 0.031(3) 0.032(3) 0.046(4) -0.006(3) 0.005(3) -0.007(3) C6 0.036(3) 0.043(4) 0.034(4) -0.013(3) 0.004(3) -0.005(3) C7 0.039(3) 0.031(3) 0.029(3) -0.002(3) 0.010(3) 0.002(3) C8 0.029(3) 0.017(3) 0.031(3) 0.002(2) 0.004(2) 0.005(2) C9 0.030(3) 0.015(3) 0.029(3) -0.005(2) 0.006(2) 0.004(2) C10 0.065(6) 0.075(6) 0.080(7) 0.002(5) 0.030(5) -0.002(5) C11 0.058(5) 0.052(5) 0.101(7) -0.002(5) -0.002(5) -0.011(4) C12 0.107(9) 0.158(13) 0.067(7) 0.020(8) 0.023(6) -0.028(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Pb1 O1 2.294(4) . ? Pb1 N1 2.475(5) . ? Pb1 O1 2.586(4) 3_566 ? Pb1 I1 3.2033(7) . ? O1 C8 1.336(7) . ? O1 Pb1 2.586(4) 3_566 ? N1 C1 1.316(8) . ? N1 C9 1.355(7) . ? N2 C10 1.294(11) . ? N2 C11 1.441(9) . ? N2 C12 1.461(12) . ? O2 C10 1.210(10) . ? C1 C2 1.406(9) . ? C1 H1 0.9300 . ? C2 C3 1.355(9) . ? C2 H2 0.9300 . ? C3 C4 1.408(9) . ? C3 H3 0.9300 . ? C4 C5 1.411(8) . ? C4 C9 1.415(8) . ? C5 C6 1.347(10) . ? C5 H5 0.9300 . ? C6 C7 1.406(9) . ? C6 H6 0.9300 . ? C7 C8 1.380(8) . ? C7 H7 0.9300 . ? C8 C9 1.432(8) . ? C10 H10 0.9300 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 O1 Pb1 N1 69.40(14) . . ? O1 Pb1 O1 72.04(14) . 3_566 ? N1 Pb1 O1 105.16(13) . 3_566 ? O1 Pb1 I1 92.27(10) . . ? N1 Pb1 I1 80.33(10) . . ? O1 Pb1 I1 159.58(9) 3_566 . ? C8 O1 Pb1 119.3(4) . . ? C8 O1 Pb1 107.4(3) . 3_566 ? Pb1 O1 Pb1 107.96(14) . 3_566 ? C1 N1 C9 119.1(5) . . ? C1 N1 Pb1 127.6(4) . . ? C9 N1 Pb1 113.2(4) . . ? C10 N2 C11 124.8(8) . . ? C10 N2 C12 119.1(8) . . ? C11 N2 C12 116.0(8) . . ? N1 C1 C2 122.5(6) . . ? N1 C1 H1 118.7 . . ? C2 C1 H1 118.7 . . ? C3 C2 C1 119.1(6) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C3 C4 120.3(6) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 123.9(6) . . ? C3 C4 C9 116.8(5) . . ? C5 C4 C9 119.2(6) . . ? C6 C5 C4 120.1(6) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 121.7(6) . . ? C5 C6 H6 119.2 . . ? C7 C6 H6 119.2 . . ? C8 C7 C6 120.7(6) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? O1 C8 C7 122.4(6) . . ? O1 C8 C9 119.2(5) . . ? C7 C8 C9 118.4(5) . . ? N1 C9 C4 122.2(5) . . ? N1 C9 C8 118.0(5) . . ? C4 C9 C8 119.9(5) . . ? O2 C10 N2 126.7(10) . . ? O2 C10 H10 116.7 . . ? N2 C10 H10 116.7 . . ? N2 C11 H11A 109.5 . . ? N2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 H12A 109.5 . . ? N2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.335 _refine_diff_density_min -2.525 _refine_diff_density_rms 0.221