# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name A.Morsali V.Safarifard _publ_contact_author_name 'Ali Morsali' _publ_contact_author_email morsali_a@yahoo.com data_1229 _database_code_depnum_ccdc_archive 'CCDC 816179' #TrackingRef '- 1229-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C3 H4 Br N3 O3 Pb' _chemical_formula_weight 417.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 8.4799(14) _cell_length_b 15.706(3) _cell_length_c 5.7500(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 765.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2312 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.18 _exptl_crystal_description Block _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 3.618 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 27.209 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.0377 _exptl_absorpt_correction_T_max 0.0842 _exptl_absorpt_process_details '(SADABS; Bruker, 2002)' _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX area-detector diffractometer' _diffrn_measurement_method '\f and \w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3929 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0420 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 25.74 _reflns_number_total 1439 _reflns_number_gt 1334 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 2002)' _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL(Bruker, 2002)' _computing_publication_material SHELXL97 _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^)+(0.0207P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.025(13) _refine_ls_number_reflns 1439 _refine_ls_number_parameters 106 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0260 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_ref 0.0534 _refine_ls_wR_factor_gt 0.0528 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.020 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pb1 Pb 0.68142(3) 0.084740(14) 0.68189(8) 0.01597(10) Uani 1 1 d . . . Br1 Br 0.66363(10) 0.00150(6) 0.22538(17) 0.0269(2) Uani 1 1 d . . . O1 O 0.6052(8) 0.2321(4) 0.8862(10) 0.0250(15) Uani 1 1 d . . . O2 O 0.4537(7) 0.3509(3) 0.8711(11) 0.0239(14) Uani 1 1 d . . . O3 O 0.9167(10) -0.0317(5) 0.681(2) 0.071(3) Uani 1 1 d D . . N1 N 0.4749(8) 0.1775(4) 0.4672(13) 0.0161(15) Uani 1 1 d . . . N2 N 0.2933(9) 0.2443(4) 0.2722(12) 0.0210(17) Uani 1 1 d . . . H2A H 0.2238 0.2547 0.1670 0.025 Uiso 1 1 calc R . . N3 N 0.3282(8) 0.2958(4) 0.4534(13) 0.0173(16) Uani 1 1 d . . . C1 C 0.4386(11) 0.2524(5) 0.5690(16) 0.0154(19) Uani 1 1 d . . . C2 C 0.3826(10) 0.1754(5) 0.2822(14) 0.0164(18) Uani 1 1 d . . . H2 H 0.3806 0.1315 0.1738 0.020 Uiso 1 1 calc R . . C3 C 0.5072(11) 0.2814(5) 0.7932(15) 0.0142(19) Uani 1 1 d . . . H3A H 0.949(11) -0.072(3) 0.605(8) 0.017 Uiso 1 1 d D . . H3B H 0.934(12) -0.034(4) 0.821(4) 0.017 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 Pb1 0.01424(16) 0.01276(14) 0.02091(17) -0.0005(2) -0.0017(3) -0.00007(10) Br1 0.0217(4) 0.0336(4) 0.0253(6) -0.0097(4) -0.0006(4) -0.0042(3) O1 0.024(4) 0.031(4) 0.021(4) -0.006(3) -0.010(3) 0.014(3) O2 0.023(4) 0.020(3) 0.029(3) -0.006(3) -0.007(3) 0.004(3) O3 0.050(5) 0.080(6) 0.084(6) -0.062(7) -0.035(6) 0.044(4) N1 0.014(4) 0.011(3) 0.023(4) -0.003(3) -0.002(3) 0.005(3) N2 0.021(4) 0.023(4) 0.019(4) -0.002(3) -0.011(3) 0.004(3) N3 0.019(4) 0.021(4) 0.012(4) -0.002(3) -0.001(3) 0.005(3) C1 0.015(5) 0.010(4) 0.021(4) 0.003(3) 0.000(4) 0.003(4) C2 0.016(4) 0.019(4) 0.014(4) -0.005(3) -0.001(3) -0.001(4) C3 0.011(5) 0.011(4) 0.021(4) -0.002(3) -0.001(4) -0.001(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 N1 2.591(6) . ? Pb1 N3 2.607(7) 3 ? Pb1 O1 2.675(6) . ? Pb1 O3 2.707(6) . ? Pb1 O2 2.745(6) 3 ? Pb1 Br1 2.9363(11) . ? Pb1 Br1 3.2340(10) 2_655 ? Br1 Pb1 3.2340(10) 2_654 ? O1 C3 1.256(10) . ? O2 C3 1.265(9) . ? O2 Pb1 2.745(6) 3_455 ? O3 H3A 0.82(2) . ? O3 H3B 0.82(2) . ? N1 C2 1.322(10) . ? N1 C1 1.350(10) . ? N2 C2 1.322(11) . ? N2 N3 1.352(10) . ? N2 H2A 0.8600 . ? N3 C1 1.335(10) . ? N3 Pb1 2.607(7) 3_455 ? C1 C3 1.485(11) . ? C2 H2 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 N1 Pb1 N3 71.2(2) . 3 ? N1 Pb1 O1 63.85(19) . . ? N3 Pb1 O1 73.4(2) 3 . ? N1 Pb1 O3 151.3(3) . . ? N3 Pb1 O3 97.7(3) 3 . ? O1 Pb1 O3 139.8(2) . . ? N1 Pb1 O2 123.38(17) . 3 ? N3 Pb1 O2 62.2(2) 3 3 ? O1 Pb1 O2 73.18(18) . 3 ? O3 Pb1 O2 68.2(2) . 3 ? N1 Pb1 Br1 77.86(16) . . ? N3 Pb1 Br1 83.94(16) 3 . ? O1 Pb1 Br1 139.94(13) . . ? O3 Pb1 Br1 74.7(2) . . ? O2 Pb1 Br1 124.16(13) 3 . ? N1 Pb1 Br1 70.18(15) . 2_655 ? N3 Pb1 Br1 140.58(15) 3 2_655 ? O1 Pb1 Br1 96.30(15) . 2_655 ? O3 Pb1 Br1 112.6(2) . 2_655 ? O2 Pb1 Br1 152.19(13) 3 2_655 ? Br1 Pb1 Br1 80.57(2) . 2_655 ? Pb1 Br1 Pb1 107.58(3) . 2_654 ? C3 O1 Pb1 120.4(5) . . ? C3 O2 Pb1 118.6(5) . 3_455 ? Pb1 O3 H3A 141(5) . . ? Pb1 O3 H3B 99(5) . . ? H3A O3 H3B 116(3) . . ? C2 N1 C1 103.6(7) . . ? C2 N1 Pb1 140.4(5) . . ? C1 N1 Pb1 116.0(5) . . ? C2 N2 N3 109.3(7) . . ? C2 N2 H2A 125.3 . . ? N3 N2 H2A 125.3 . . ? C1 N3 N2 103.4(6) . . ? C1 N3 Pb1 116.8(6) . 3_455 ? N2 N3 Pb1 135.6(5) . 3_455 ? N3 C1 N1 112.9(8) . . ? N3 C1 C3 123.4(8) . . ? N1 C1 C3 123.6(7) . . ? N1 C2 N2 110.7(7) . . ? N1 C2 H2 124.6 . . ? N2 C2 H2 124.6 . . ? O1 C3 O2 128.2(8) . . ? O1 C3 C1 116.1(7) . . ? O2 C3 C1 115.6(8) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2A O1 0.86 1.91 2.758(9) 167.0 3_454 O3 H3A O2 0.82(2) 1.99(3) 2.789(10) 166(7) 4_644 O3 H3B O3 0.82(2) 2.63(5) 3.354(10) 148(8) 2_755 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.74 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.343 _refine_diff_density_min -1.659 _refine_diff_density_rms 0.183