# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Ali Morsali' _publ_contact_author_email morsali_a@modares.ac.ir _publ_author_name A.Morsali # Attachment '220-A_07mz516m.cif' data_07mz516m _database_code_depnum_ccdc_archive 'CCDC 686654' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Br N O2 Pb' _chemical_formula_weight 409.20 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' Br Br -0.2901 2.4595 '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 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 11.695(4) _cell_length_b 17.175(6) _cell_length_c 7.861(3) _cell_angle_alpha 90.00 _cell_angle_beta 91.037(7) _cell_angle_gamma 90.00 _cell_volume 1578.7(9) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2309 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 30.33 _exptl_crystal_description block _exptl_crystal_colour brown _exptl_crystal_size_max 0.11 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1440 _exptl_absorpt_coefficient_mu 26.379 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.048 _exptl_absorpt_correction_T_max 0.348 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2007)' _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 'Bruker AXS SMART APEX CCD diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6336 _diffrn_reflns_av_R_equivalents 0.0748 _diffrn_reflns_av_sigmaI/netI 0.0730 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 28.28 _reflns_number_total 1932 _reflns_number_gt 1524 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Apex2 v2.1-4 (Bruker, 2007)' _computing_cell_refinement 'Apex2 v2.1-4' _computing_data_reduction 'Apex2 v2.1-4' _computing_structure_solution 'SHELXTL 6.14 (Bruker, 2000-2003)' _computing_structure_refinement 'SHELXTL 6.14' _computing_molecular_graphics 'SHELXTL 6.14' _computing_publication_material 'SHELXTL 6.14' _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^)+(0.1945P)^2^+76.0958P] 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 1932 _refine_ls_number_parameters 100 _refine_ls_number_restraints 74 _refine_ls_R_factor_all 0.1169 _refine_ls_R_factor_gt 0.0972 _refine_ls_wR_factor_ref 0.2907 _refine_ls_wR_factor_gt 0.2662 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.084 _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 Br1 Br 0.6644(2) 0.43940(11) -0.1048(3) 0.0254(6) Uani 1 1 d . . . C1 C 0.7203(18) 0.2641(11) 0.260(3) 0.021(3) Uani 1 1 d U . . H1 H 0.7777 0.2532 0.1835 0.025 Uiso 1 1 calc R . . C2 C 0.6672(17) 0.2037(12) 0.329(3) 0.020(3) Uani 1 1 d U . . H2 H 0.6887 0.1529 0.3040 0.023 Uiso 1 1 calc R . . C3 C 0.5770(18) 0.2190(11) 0.442(3) 0.019(3) Uani 1 1 d U . . C4 C 0.5484(19) 0.2954(11) 0.475(3) 0.021(3) Uani 1 1 d U . . H4 H 0.4877 0.3068 0.5458 0.026 Uiso 1 1 calc R . . C5 C 0.611(2) 0.3556(12) 0.402(3) 0.027(3) Uani 1 1 d U . . H5 H 0.5935 0.4068 0.4296 0.032 Uiso 1 1 calc R . . C6 C 0.5141(19) 0.1513(11) 0.524(3) 0.021(3) Uani 1 1 d U . . N1 N 0.6979(17) 0.3418(11) 0.292(3) 0.026(3) Uani 1 1 d U . . O1 O 0.5589(14) 0.0867(8) 0.537(2) 0.026(3) Uani 1 1 d U . . O2 O 0.4165(13) 0.1662(8) 0.576(2) 0.023(3) Uani 1 1 d U . . Pb1 Pb 0.81920(7) 0.44578(4) 0.18176(10) 0.0224(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 Br1 0.0327(14) 0.0117(9) 0.0322(12) 0.0012(7) 0.0054(10) -0.0028(8) C1 0.018(7) 0.010(6) 0.036(7) 0.000(5) 0.001(6) -0.006(5) C2 0.013(6) 0.010(6) 0.036(7) 0.003(5) 0.002(5) -0.007(5) C3 0.013(6) 0.009(5) 0.034(6) 0.003(5) 0.004(5) 0.001(5) C4 0.022(7) 0.008(5) 0.034(7) 0.006(5) 0.005(6) 0.003(5) C5 0.027(7) 0.013(6) 0.041(7) 0.002(5) 0.008(6) -0.003(5) C6 0.018(6) 0.010(5) 0.036(6) 0.002(5) 0.004(5) 0.000(4) N1 0.025(7) 0.014(6) 0.039(7) -0.001(5) 0.005(6) -0.003(5) O1 0.025(7) 0.012(5) 0.040(7) 0.003(5) 0.001(6) 0.004(5) O2 0.014(6) 0.014(6) 0.041(7) 0.004(5) 0.004(5) -0.007(4) Pb1 0.0314(6) 0.0083(5) 0.0276(6) 0.0005(2) 0.0048(4) 0.0006(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 Br1 Pb1 2.867(3) . ? Br1 Pb1 3.176(2) 6_565 ? C1 C2 1.33(3) . ? C1 N1 1.38(3) . ? C1 H1 0.9300 . ? C2 C3 1.41(3) . ? C2 H2 0.9300 . ? C3 C4 1.38(3) . ? C3 C6 1.53(3) . ? C4 C5 1.40(3) . ? C4 H4 0.9300 . ? C5 N1 1.36(3) . ? C5 H5 0.9300 . ? C6 O1 1.23(2) . ? C6 O2 1.24(3) . ? N1 Pb1 2.451(19) . ? O1 Pb1 2.669(16) 7_656 ? O2 Pb1 2.392(14) 8_456 ? Pb1 O2 2.392(14) 8 ? Pb1 O1 2.669(16) 7_656 ? Pb1 Br1 3.176(2) 6_566 ? 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 Pb1 Br1 Pb1 91.92(7) . 6_565 ? C2 C1 N1 126(2) . . ? C2 C1 H1 117.1 . . ? N1 C1 H1 117.1 . . ? C1 C2 C3 118(2) . . ? C1 C2 H2 121.0 . . ? C3 C2 H2 121.0 . . ? C4 C3 C2 118.8(18) . . ? C4 C3 C6 121.6(18) . . ? C2 C3 C6 119.6(17) . . ? C3 C4 C5 120(2) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 122(2) . . ? N1 C5 H5 118.9 . . ? C4 C5 H5 118.9 . . ? O1 C6 O2 123(2) . . ? O1 C6 C3 120.9(19) . . ? O2 C6 C3 115.6(17) . . ? C5 N1 C1 115.4(19) . . ? C5 N1 Pb1 122.6(14) . . ? C1 N1 Pb1 121.7(14) . . ? C6 O1 Pb1 118.3(14) . 7_656 ? C6 O2 Pb1 113.1(13) . 8_456 ? O2 Pb1 N1 79.6(6) 8 . ? O2 Pb1 O1 82.6(5) 8 7_656 ? N1 Pb1 O1 81.8(6) . 7_656 ? O2 Pb1 Br1 89.6(4) 8 . ? N1 Pb1 Br1 83.7(5) . . ? O1 Pb1 Br1 164.5(3) 7_656 . ? O2 Pb1 Br1 164.2(4) 8 6_566 ? N1 Pb1 Br1 85.8(5) . 6_566 ? O1 Pb1 Br1 89.6(3) 7_656 6_566 ? Br1 Pb1 Br1 94.64(8) . 6_566 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 2(3) . . . . ? C1 C2 C3 C4 0(3) . . . . ? C1 C2 C3 C6 -180(2) . . . . ? C2 C3 C4 C5 -2(3) . . . . ? C6 C3 C4 C5 177(2) . . . . ? C3 C4 C5 N1 3(4) . . . . ? C4 C3 C6 O1 -158(2) . . . . ? C2 C3 C6 O1 22(3) . . . . ? C4 C3 C6 O2 22(3) . . . . ? C2 C3 C6 O2 -158(2) . . . . ? C4 C5 N1 C1 -1(4) . . . . ? C4 C5 N1 Pb1 -174.9(17) . . . . ? C2 C1 N1 C5 -2(4) . . . . ? C2 C1 N1 Pb1 172.4(17) . . . . ? O2 C6 O1 Pb1 -89(2) . . . 7_656 ? C3 C6 O1 Pb1 91(2) . . . 7_656 ? O1 C6 O2 Pb1 -4(3) . . . 8_456 ? C3 C6 O2 Pb1 175.3(14) . . . 8_456 ? C5 N1 Pb1 O2 173(2) . . . 8 ? C1 N1 Pb1 O2 -1.0(16) . . . 8 ? C5 N1 Pb1 O1 88.6(19) . . . 7_656 ? C1 N1 Pb1 O1 -84.9(17) . . . 7_656 ? C5 N1 Pb1 Br1 -96.7(19) . . . . ? C1 N1 Pb1 Br1 89.7(17) . . . . ? C5 N1 Pb1 Br1 -1.6(19) . . . 6_566 ? C1 N1 Pb1 Br1 -175.1(17) . . . 6_566 ? Pb1 Br1 Pb1 O2 -92.1(4) 6_565 . . 8 ? Pb1 Br1 Pb1 N1 -171.7(5) 6_565 . . . ? Pb1 Br1 Pb1 O1 -151.5(13) 6_565 . . 7_656 ? Pb1 Br1 Pb1 Br1 103.14(9) 6_565 . . 6_566 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 10.377 _refine_diff_density_min -7.399 _refine_diff_density_rms 0.880 # Attachment 'morsali2.cif' data_morsali2 _database_code_depnum_ccdc_archive 'CCDC 739062' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 Br N O3 Pb' _chemical_formula_weight 425.20 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' Br Br -0.2901 2.4595 '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.0675(3) _cell_length_b 6.9454(3) _cell_length_c 19.8525(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 836.61(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.376 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 24.905 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6378 _diffrn_reflns_av_R_equivalents 0.0858 _diffrn_reflns_av_sigmaI/netI 0.0550 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 26.50 _reflns_number_total 1738 _reflns_number_gt 1725 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0000P)^2^+26.2170P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0026(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.40(6) _refine_ls_number_reflns 1738 _refine_ls_number_parameters 117 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0490 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.231 _refine_ls_restrained_S_all 1.242 _refine_ls_shift/su_max 1.386 _refine_ls_shift/su_mean 0.078 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 C1 C 0.738(5) 0.459(3) 0.3334(9) 0.046(6) Uani 1 1 d . . . C2 C 0.559(4) 0.389(4) 0.2987(10) 0.048(6) Uani 1 1 d . . . H2 H 0.4281 0.3588 0.3207 0.058 Uiso 1 1 calc R . . C3 C 0.582(4) 0.365(4) 0.2294(9) 0.046(5) Uani 1 1 d . . . H3 H 0.4689 0.3039 0.2062 0.055 Uiso 1 1 calc R . . C4 C 0.930(4) 0.487(4) 0.2311(9) 0.044(6) Uani 1 1 d . . . H4 H 1.0590 0.5161 0.2079 0.053 Uiso 1 1 calc R . . C5 C 0.927(4) 0.511(3) 0.2993(10) 0.043(5) Uani 1 1 d . . . H5 H 1.0487 0.5597 0.3221 0.052 Uiso 1 1 calc R . . C6 C 0.729(5) 0.490(3) 0.4120(8) 0.041(5) Uani 1 1 d . . . N1 N 0.752(3) 0.423(2) 0.1955(6) 0.034(3) Uani 1 1 d . . . Br1 Br 0.2286(7) 0.5241(3) 0.57643(9) 0.0617(8) Uani 1 1 d . . . O1 O 0.551(5) 0.503(3) 0.4352(8) 0.076(7) Uani 1 1 d . . . O2 O 0.915(5) 0.513(3) 0.4424(10) 0.083(8) Uani 1 1 d . . . Pb1 Pb 0.72814(11) 0.61325(9) 0.55350(3) 0.0285(2) Uani 1 1 d . . . O3 O 0.727(3) 0.2773(17) 0.5721(7) 0.050(4) Uani 1 1 d D . . H3A H 0.88(3) 0.24(3) 0.555(15) 0.075 Uiso 1 1 d D . . H3B H 0.63(3) 0.17(3) 0.558(15) 0.075 Uiso 1 1 d 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 C1 0.074(17) 0.032(8) 0.032(8) 0.007(7) 0.001(13) 0.026(14) C2 0.064(14) 0.044(12) 0.037(11) 0.012(11) 0.020(10) -0.016(13) C3 0.071(15) 0.043(12) 0.024(9) -0.005(9) 0.000(9) 0.001(13) C4 0.046(12) 0.065(15) 0.023(9) -0.006(10) -0.008(9) -0.020(12) C5 0.060(14) 0.035(11) 0.034(10) 0.011(10) -0.006(10) -0.003(11) C6 0.068(16) 0.036(9) 0.020(8) -0.005(7) 0.020(11) 0.007(13) N1 0.039(8) 0.043(8) 0.021(6) -0.005(5) 0.004(7) -0.015(11) Br1 0.117(2) 0.0414(10) 0.0264(8) -0.0015(7) 0.0015(14) -0.0037(18) O1 0.16(2) 0.041(11) 0.026(10) -0.012(9) 0.011(12) -0.003(13) O2 0.17(2) 0.048(11) 0.028(8) -0.012(10) -0.047(13) 0.037(13) Pb1 0.0271(3) 0.0355(3) 0.0227(3) -0.0008(2) 0.0001(3) 0.0008(3) O3 0.071(11) 0.024(6) 0.055(8) -0.005(5) -0.034(10) 0.002(8) _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 C1 C5 1.38(3) . ? C1 C2 1.38(3) . ? C1 C6 1.58(2) . ? C2 C3 1.39(3) . ? C2 H2 0.9300 . ? C3 N1 1.30(3) . ? C3 H3 0.9300 . ? C4 C5 1.36(3) . ? C4 N1 1.36(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 O1 1.18(3) . ? C6 O2 1.29(3) . ? Br1 Pb1 3.127(4) . ? Br1 Pb1 3.132(4) 1_455 ? O1 Pb1 2.695(19) . ? O2 Pb1 2.58(2) . ? Pb1 O3 2.362(12) . ? Pb1 Br1 3.132(4) 1_655 ? O3 H3A 1.01(9) . ? O3 H3B 1.01(8) . ? 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 C5 C1 C2 120.3(17) . . ? C5 C1 C6 119(2) . . ? C2 C1 C6 121(2) . . ? C1 C2 C3 117(2) . . ? C1 C2 H2 121.4 . . ? C3 C2 H2 121.4 . . ? N1 C3 C2 124(2) . . ? N1 C3 H3 118.1 . . ? C2 C3 H3 118.1 . . ? C5 C4 N1 123(2) . . ? C5 C4 H4 118.6 . . ? N1 C4 H4 118.5 . . ? C4 C5 C1 118(2) . . ? C4 C5 H5 121.1 . . ? C1 C5 H5 121.1 . . ? O1 C6 O2 127.7(18) . . ? O1 C6 C1 116(2) . . ? O2 C6 C1 117(2) . . ? C3 N1 C4 117.5(15) . . ? Pb1 Br1 Pb1 151.58(7) . 1_455 ? C6 O1 Pb1 89.8(16) . . ? C6 O2 Pb1 92.7(16) . . ? O3 Pb1 O2 82.4(6) . . ? O3 Pb1 O1 81.6(5) . . ? O2 Pb1 O1 49.7(7) . . ? O3 Pb1 Br1 77.2(5) . . ? O2 Pb1 Br1 119.9(6) . . ? O1 Pb1 Br1 71.6(6) . . ? O3 Pb1 Br1 77.6(5) . 1_655 ? O2 Pb1 Br1 69.1(5) . 1_655 ? O1 Pb1 Br1 117.2(6) . 1_655 ? Br1 Pb1 Br1 151.58(7) . 1_655 ? Pb1 O3 H3A 102(10) . . ? Pb1 O3 H3B 134(10) . . ? H3A O3 H3B 104(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 C1 C2 C3 3(4) . . . . ? C6 C1 C2 C3 -180(2) . . . . ? C1 C2 C3 N1 -7(4) . . . . ? N1 C4 C5 C1 3(4) . . . . ? C2 C1 C5 C4 -1(3) . . . . ? C6 C1 C5 C4 -178(2) . . . . ? C5 C1 C6 O1 157(2) . . . . ? C2 C1 C6 O1 -21(3) . . . . ? C5 C1 C6 O2 -18(3) . . . . ? C2 C1 C6 O2 164(2) . . . . ? C2 C3 N1 C4 9(4) . . . . ? C5 C4 N1 C3 -7(4) . . . . ? O2 C6 O1 Pb1 4(2) . . . . ? C1 C6 O1 Pb1 -170.0(14) . . . . ? O1 C6 O2 Pb1 -5(2) . . . . ? C1 C6 O2 Pb1 169.7(14) . . . . ? C6 O2 Pb1 O3 87.5(13) . . . . ? C6 O2 Pb1 O1 2.1(11) . . . . ? C6 O2 Pb1 Br1 17.0(14) . . . . ? C6 O2 Pb1 Br1 167.1(14) . . . 1_655 ? C6 O1 Pb1 O3 -89.4(15) . . . . ? C6 O1 Pb1 O2 -2.3(12) . . . . ? C6 O1 Pb1 Br1 -168.7(15) . . . . ? C6 O1 Pb1 Br1 -18.1(16) . . . 1_655 ? Pb1 Br1 Pb1 O3 -151.9(4) 1_455 . . . ? Pb1 Br1 Pb1 O2 -78.6(5) 1_455 . . . ? Pb1 Br1 Pb1 O1 -66.7(5) 1_455 . . . ? Pb1 Br1 Pb1 Br1 180.0 1_455 . . 1_655 ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 2.163 _refine_diff_density_min -2.453 _refine_diff_density_rms 0.363