# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sq #TrackingRef '107.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 Cl N5 O3 Pb' _chemical_formula_sum 'C14 H14 Cl N5 O3 Pb' _chemical_formula_weight 542.94 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' Cl Cl 0.1484 0.1585 '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 14.0972(11) _cell_length_b 8.2977(8) _cell_length_c 15.9525(14) _cell_angle_alpha 90.00 _cell_angle_beta 104.203(7) _cell_angle_gamma 90.00 _cell_volume 1809.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 12562 _cell_measurement_theta_min 2.45 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.994 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 9.496 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.663 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'MULABS (Blessing, 1995) in PLATON (Spek, 2009)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'STOE IPDS 2T Image Plate diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean '0.15 mm' _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 8593 _diffrn_reflns_av_R_equivalents 0.0706 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.63 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3532 _reflns_number_gt 2575 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-Area 1.52 (Stoe & Cie GmbH, 2009)' _computing_cell_refinement 'X-Area 1.52' _computing_data_reduction 'X-Area 1.52' _computing_structure_solution 'SHELXTL (Sheldrick, 2008)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL, PLATON (Spek, 2009)' _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^)+(0.0710P)^2^+26.8892P] 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 3532 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0777 _refine_ls_wR_factor_ref 0.1821 _refine_ls_wR_factor_gt 0.1703 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pb1 Pb 1.50034(4) -0.01619(6) 0.37061(4) 0.0394(2) Uani 1 1 d . . . N4 N 0.9601(12) 0.529(2) 0.3771(14) 0.075(5) Uani 1 1 d . . . C8 C 0.8900(13) 0.463(3) 0.4021(14) 0.065(6) Uani 1 1 d . . . C11 C 1.7216(14) -0.485(2) 0.4240(14) 0.061(5) Uani 1 1 d . . . H11A H 1.7138 -0.5935 0.4342 0.073 Uiso 1 1 calc R . . C6 C 1.1047(18) 0.483(3) 0.3475(16) 0.076(7) Uani 1 1 d . . . C2 C 1.2783(16) 0.435(3) 0.3449(17) 0.082(8) Uani 1 1 d . . . H2A H 1.2871 0.5451 0.3384 0.098 Uiso 1 1 calc R . . C12 C 1.8085(13) -0.424(3) 0.4098(13) 0.055(5) Uani 1 1 d . . . N2 N 1.6573(12) -0.220(2) 0.4173(14) 0.074(6) Uani 1 1 d . . . N3 N 1.0352(12) 0.422(2) 0.3723(14) 0.076(5) Uani 1 1 d . . . N1 N 1.3471(10) 0.1754(19) 0.3536(11) 0.058(4) Uani 1 1 d . . . C3 C 1.1899(14) 0.381(3) 0.3467(14) 0.064(6) Uani 1 1 d . . . O3 O 1.4746(11) -0.267(2) 0.2469(12) 0.100(7) Uani 1 1 d . . . C1 C 1.3560(15) 0.334(3) 0.3523(16) 0.072(6) Uani 1 1 d . . . H1A H 1.4177 0.3785 0.3567 0.086 Uiso 1 1 calc R . . C4 C 1.1796(16) 0.217(3) 0.3511(19) 0.087(8) Uani 1 1 d . . . H4A H 1.1209 0.1714 0.3559 0.105 Uiso 1 1 calc R . . C5 C 1.2601(14) 0.121(3) 0.3482(19) 0.087(8) Uani 1 1 d . . . H5A H 1.2503 0.0106 0.3418 0.105 Uiso 1 1 calc R . . C14 C 1.7458(17) -0.161(3) 0.414(2) 0.099(10) Uani 1 1 d . . . H14A H 1.7560 -0.0504 0.4157 0.119 Uiso 1 1 calc R . . O2 O 1.3434(12) -0.175(2) 0.2676(12) 0.097(6) Uani 1 1 d . . . C7 C 1.112(2) 0.658(3) 0.322(2) 0.121(13) Uani 1 1 d . . . H7A H 1.0585 0.7178 0.3334 0.181 Uiso 1 1 calc R . . H7B H 1.1112 0.6646 0.2621 0.181 Uiso 1 1 calc R . . H7C H 1.1728 0.7026 0.3559 0.181 Uiso 1 1 calc R . . O1 O 1.3412(12) -0.365(2) 0.1786(13) 0.104(6) Uani 1 1 d . . . C9 C 0.8849(16) 0.291(3) 0.424(2) 0.096(9) Uani 1 1 d . . . H9A H 0.8177 0.2582 0.4117 0.143 Uiso 1 1 calc R . . H9B H 0.9152 0.2750 0.4837 0.143 Uiso 1 1 calc R . . H9C H 0.9185 0.2285 0.3892 0.143 Uiso 1 1 calc R . . Cl1 Cl 1.4216(4) -0.1910(7) 0.4873(4) 0.0701(14) Uani 1 1 d . . . N5 N 1.3892(12) -0.2704(19) 0.2322(10) 0.052(4) Uani 1 1 d . . . C10 C 1.6471(13) -0.374(3) 0.4220(16) 0.071(7) Uani 1 1 d . . . H10A H 1.5860 -0.4132 0.4241 0.086 Uiso 1 1 calc R . . C13 C 1.8210(13) -0.262(2) 0.4067(19) 0.078(8) Uani 1 1 d . . . H13A H 1.8797 -0.2200 0.4000 0.093 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 0.0328(3) 0.0362(3) 0.0512(4) -0.0006(3) 0.0139(2) 0.0047(3) N4 0.040(8) 0.077(12) 0.110(15) -0.004(11) 0.021(9) 0.027(8) C8 0.041(9) 0.070(14) 0.075(14) -0.012(11) -0.005(9) 0.027(9) C11 0.051(10) 0.054(12) 0.076(14) 0.004(10) 0.015(9) 0.009(8) C6 0.082(15) 0.081(16) 0.077(15) -0.003(13) 0.042(13) 0.027(12) C2 0.062(12) 0.090(16) 0.110(19) 0.022(14) 0.053(13) 0.047(12) C12 0.045(9) 0.066(12) 0.059(12) -0.007(10) 0.019(8) 0.012(9) N2 0.044(9) 0.063(11) 0.118(17) -0.019(11) 0.024(10) 0.015(8) N3 0.046(8) 0.078(12) 0.111(16) -0.001(11) 0.030(10) 0.022(8) N1 0.041(8) 0.058(11) 0.075(12) -0.005(9) 0.015(7) 0.012(7) C3 0.048(10) 0.076(15) 0.070(14) -0.002(11) 0.019(9) 0.028(10) O3 0.043(9) 0.146(18) 0.100(13) -0.057(12) -0.004(9) 0.004(9) C1 0.061(12) 0.068(15) 0.100(18) 0.020(12) 0.046(12) 0.022(10) C4 0.047(11) 0.075(15) 0.15(3) -0.031(16) 0.037(13) 0.010(11) C5 0.044(11) 0.060(14) 0.16(3) -0.030(15) 0.025(13) 0.003(9) C14 0.065(14) 0.046(13) 0.19(3) 0.013(15) 0.043(16) 0.024(10) O2 0.065(10) 0.110(14) 0.117(15) -0.043(12) 0.027(9) 0.011(9) C7 0.12(2) 0.10(2) 0.18(3) 0.07(2) 0.11(2) 0.069(18) O1 0.066(10) 0.132(16) 0.114(15) -0.059(13) 0.021(10) -0.019(10) C9 0.052(13) 0.066(14) 0.17(3) -0.004(17) 0.020(15) 0.017(11) Cl1 0.063(3) 0.068(3) 0.079(4) 0.002(3) 0.019(3) -0.016(3) N5 0.062(10) 0.052(9) 0.047(10) -0.016(8) 0.024(8) -0.010(7) C10 0.032(9) 0.071(15) 0.110(19) -0.016(13) 0.017(10) 0.023(8) C13 0.027(9) 0.060(14) 0.15(2) 0.017(13) 0.026(11) 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 N1 2.643(14) . ? Pb1 N2 2.740(16) . ? Pb1 O2 2.746(17) . ? Pb1 Cl1 2.796(5) . ? Pb1 Cl1 2.843(6) 3_856 ? N4 C8 1.28(3) . ? N4 N3 1.40(2) . ? C8 C9 1.47(3) . ? C8 C12 1.51(2) 1_465 ? C11 C10 1.39(2) . ? C11 C12 1.39(3) . ? C11 H11A 0.9300 . ? C6 N3 1.25(3) . ? C6 C3 1.48(3) . ? C6 C7 1.52(3) . ? C2 C3 1.33(3) . ? C2 C1 1.36(2) . ? C2 H2A 0.9300 . ? C12 C13 1.36(3) . ? C12 C8 1.51(2) 1_645 ? N2 C10 1.29(3) . ? N2 C14 1.36(3) . ? N1 C5 1.29(2) . ? N1 C1 1.32(3) . ? C3 C4 1.37(3) . ? O3 N5 1.169(19) . ? C1 H1A 0.9300 . ? C4 C5 1.40(3) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C14 C13 1.38(3) . ? C14 H14A 0.9300 . ? O2 N5 1.24(2) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? O1 N5 1.23(2) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? Cl1 Pb1 2.843(6) 3_856 ? C10 H10A 0.9300 . ? C13 H13A 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 N2 170.1(6) . . ? N1 Pb1 O2 73.0(5) . . ? N2 Pb1 O2 110.2(5) . . ? N1 Pb1 Cl1 86.1(4) . . ? N2 Pb1 Cl1 85.7(5) . . ? O2 Pb1 Cl1 75.9(4) . . ? N1 Pb1 Cl1 82.2(4) . 3_856 ? N2 Pb1 Cl1 91.6(4) . 3_856 ? O2 Pb1 Cl1 149.8(4) . 3_856 ? Cl1 Pb1 Cl1 85.54(15) . 3_856 ? C8 N4 N3 113.6(18) . . ? N4 C8 C9 125.0(18) . . ? N4 C8 C12 114.9(19) . 1_465 ? C9 C8 C12 120(2) . 1_465 ? C10 C11 C12 116.6(19) . . ? C10 C11 H11A 121.7 . . ? C12 C11 H11A 121.7 . . ? N3 C6 C3 118(2) . . ? N3 C6 C7 125.9(19) . . ? C3 C6 C7 116(2) . . ? C3 C2 C1 122(2) . . ? C3 C2 H2A 119.1 . . ? C1 C2 H2A 119.1 . . ? C13 C12 C11 119.3(17) . . ? C13 C12 C8 120.3(18) . 1_645 ? C11 C12 C8 120.3(19) . 1_645 ? C10 N2 C14 118.5(17) . . ? C10 N2 Pb1 122.3(13) . . ? C14 N2 Pb1 117.1(15) . . ? C6 N3 N4 115(2) . . ? C5 N1 C1 116.0(17) . . ? C5 N1 Pb1 122.5(14) . . ? C1 N1 Pb1 121.4(12) . . ? C2 C3 C4 116.8(18) . . ? C2 C3 C6 125(2) . . ? C4 C3 C6 118(2) . . ? N1 C1 C2 122(2) . . ? N1 C1 H1A 118.8 . . ? C2 C1 H1A 118.8 . . ? C3 C4 C5 118(2) . . ? C3 C4 H4A 121.2 . . ? C5 C4 H4A 121.2 . . ? N1 C5 C4 125(2) . . ? N1 C5 H5A 117.7 . . ? C4 C5 H5A 117.7 . . ? N2 C14 C13 121(2) . . ? N2 C14 H14A 119.4 . . ? C13 C14 H14A 119.4 . . ? N5 O2 Pb1 98.4(12) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? Pb1 Cl1 Pb1 94.46(15) . 3_856 ? O3 N5 O1 121.1(17) . . ? O3 N5 O2 121.3(17) . . ? O1 N5 O2 117.5(18) . . ? N2 C10 C11 124(2) . . ? N2 C10 H10A 117.9 . . ? C11 C10 H10A 117.9 . . ? C12 C13 C14 119.4(19) . . ? C12 C13 H13A 120.3 . . ? C14 C13 H13A 120.3 . . ? 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 N3 N4 C8 C9 -1(4) . . . . ? N3 N4 C8 C12 178.7(18) . . . 1_465 ? C10 C11 C12 C13 9(3) . . . . ? C10 C11 C12 C8 -174(2) . . . 1_645 ? N1 Pb1 N2 C10 81(4) . . . . ? O2 Pb1 N2 C10 -27(2) . . . . ? Cl1 Pb1 N2 C10 46.5(19) . . . . ? Cl1 Pb1 N2 C10 132(2) 3_856 . . . ? N1 Pb1 N2 C14 -116(3) . . . . ? O2 Pb1 N2 C14 136(2) . . . . ? Cl1 Pb1 N2 C14 -150(2) . . . . ? Cl1 Pb1 N2 C14 -65(2) 3_856 . . . ? C3 C6 N3 N4 176(2) . . . . ? C7 C6 N3 N4 -1(4) . . . . ? C8 N4 N3 C6 180(2) . . . . ? N2 Pb1 N1 C5 -76(4) . . . . ? O2 Pb1 N1 C5 35(2) . . . . ? Cl1 Pb1 N1 C5 -42(2) . . . . ? Cl1 Pb1 N1 C5 -128(2) 3_856 . . . ? N2 Pb1 N1 C1 102(3) . . . . ? O2 Pb1 N1 C1 -147.1(18) . . . . ? Cl1 Pb1 N1 C1 136.5(17) . . . . ? Cl1 Pb1 N1 C1 50.4(17) 3_856 . . . ? C1 C2 C3 C4 -4(4) . . . . ? C1 C2 C3 C6 174(2) . . . . ? N3 C6 C3 C2 -161(3) . . . . ? C7 C6 C3 C2 16(4) . . . . ? N3 C6 C3 C4 17(4) . . . . ? C7 C6 C3 C4 -167(3) . . . . ? C5 N1 C1 C2 -1(4) . . . . ? Pb1 N1 C1 C2 -179.0(18) . . . . ? C3 C2 C1 N1 6(4) . . . . ? C2 C3 C4 C5 -4(4) . . . . ? C6 C3 C4 C5 178(2) . . . . ? C1 N1 C5 C4 -8(4) . . . . ? Pb1 N1 C5 C4 171(2) . . . . ? C3 C4 C5 N1 10(5) . . . . ? C10 N2 C14 C13 6(4) . . . . ? Pb1 N2 C14 C13 -158(2) . . . . ? N1 Pb1 O2 N5 159.0(15) . . . . ? N2 Pb1 O2 N5 -30.9(15) . . . . ? Cl1 Pb1 O2 N5 -110.8(14) . . . . ? Cl1 Pb1 O2 N5 -164.7(9) 3_856 . . . ? N1 Pb1 Cl1 Pb1 -82.5(4) . . . 3_856 ? N2 Pb1 Cl1 Pb1 91.9(4) . . . 3_856 ? O2 Pb1 Cl1 Pb1 -156.0(4) . . . 3_856 ? Cl1 Pb1 Cl1 Pb1 0.0 3_856 . . 3_856 ? Pb1 O2 N5 O3 -2(2) . . . . ? Pb1 O2 N5 O1 -179.4(17) . . . . ? C14 N2 C10 C11 0(4) . . . . ? Pb1 N2 C10 C11 163.3(17) . . . . ? C12 C11 C10 N2 -8(4) . . . . ? C11 C12 C13 C14 -3(4) . . . . ? C8 C12 C13 C14 180(2) 1_645 . . . ? N2 C14 C13 C12 -5(5) . . . . ? 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 _geom_hbond_publ_flag C5 H5A O2 0.93 2.50 3.13(3) 125 . y C9 H9A O1 0.96 2.57 3.47(3) 156 2_755 y C14 H14A O1 0.93 2.35 2.97(3) 124 2_855 y _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 3.658 _refine_diff_density_min -2.447 _refine_diff_density_rms 0.234 # SQUEEZE RESULTS (APPEND TO CIF) # Note: Data are Listed for all Voids in the P1 Unit Cell # i.e. Centre of Gravity, Solvent Accessible Volume, # Recovered number of Electrons in the Void and # Details about the Squeezed Material 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 _platon_squeeze_void_content 1 0.000 0.000 0.500 37 6 ' ' 2 1.000 0.500 0.000 37 6 ' ' _platon_squeeze_details ; ; _database_code_depnum_ccdc_archive 'CCDC 854760' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_sk15 #TrackingRef 'sk15.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H14 Cl2 N4 Pb' _chemical_formula_weight 516.39 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' 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 P2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' _cell_length_a 12.805(1) _cell_length_b 4.0989(3) _cell_length_c 16.246(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.729(1) _cell_angle_gamma 90.00 _cell_volume 846.8(1) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5008 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.12 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.025 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 10.274 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2331 _exptl_absorpt_correction_T_max 0.5776 _exptl_absorpt_process_details 'Bruker SADABS' _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \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 6148 _diffrn_reflns_av_R_equivalents 0.0235 _diffrn_reflns_av_sigmaI/netI 0.0226 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1654 _reflns_number_gt 1637 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0237P)^2^+0.1900P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1654 _refine_ls_number_parameters 96 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0157 _refine_ls_R_factor_gt 0.0155 _refine_ls_wR_factor_ref 0.0389 _refine_ls_wR_factor_gt 0.0388 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 -0.03079(3) 0.2500 0.02104(6) Uani 1 2 d S . . Cl1 Cl 0.09546(7) 0.44970(17) 0.35713(5) 0.03528(18) Uani 1 1 d . . . N1 N 0.1610(2) 0.0415(6) 0.16209(19) 0.0329(6) Uani 1 1 d . . . N2 N 0.4646(2) 0.4573(6) 0.02817(18) 0.0297(6) Uani 1 1 d . . . C1 C 0.2508(2) 0.1975(9) 0.18867(17) 0.0378(7) Uani 1 1 d . . . H1A H 0.2632 0.2554 0.2443 0.045 Uiso 1 1 calc R . . C2 C 0.3255(2) 0.2757(8) 0.13758(17) 0.0350(7) Uani 1 1 d . . . H2A H 0.3867 0.3836 0.1588 0.042 Uiso 1 1 calc R . . C3 C 0.30900(19) 0.1926(7) 0.05403(16) 0.0253(5) Uani 1 1 d . . . C4 C 0.2166(3) 0.0294(6) 0.0267(2) 0.0304(7) Uani 1 1 d . . . H4A H 0.2023 -0.0320 -0.0286 0.037 Uiso 1 1 calc R . . C5 C 0.1457(3) -0.0414(7) 0.0824(2) 0.0353(7) Uani 1 1 d . . . H5A H 0.0844 -0.1526 0.0631 0.042 Uiso 1 1 calc R . . C6 C 0.38635(19) 0.2830(7) -0.00415(16) 0.0248(5) Uani 1 1 d . . . C7 C 0.3667(2) 0.1730(8) -0.09262(17) 0.0323(6) Uani 1 1 d . . . H7D H 0.4227 0.2483 -0.1223 0.048 Uiso 1 1 calc R . . H7A H 0.3012 0.2613 -0.1177 0.048 Uiso 1 1 calc R . . H7B H 0.3638 -0.0609 -0.0946 0.048 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 0.02064(9) 0.01859(9) 0.02415(9) 0.000 0.00375(6) 0.000 Cl1 0.0400(5) 0.0305(4) 0.0321(4) 0.0000(3) -0.0096(3) -0.0018(3) N1 0.0262(15) 0.0429(16) 0.0309(15) 0.0020(10) 0.0092(12) -0.0013(10) N2 0.0234(14) 0.0397(15) 0.0270(13) -0.0018(10) 0.0082(12) -0.0030(9) C1 0.0316(16) 0.057(2) 0.0249(14) -0.0026(14) 0.0034(12) -0.0056(14) C2 0.0271(14) 0.0506(19) 0.0273(14) -0.0049(13) 0.0025(11) -0.0098(13) C3 0.0205(13) 0.0289(15) 0.0266(13) 0.0017(11) 0.0036(10) 0.0029(10) C4 0.0282(17) 0.0378(18) 0.0251(16) -0.0006(11) 0.0025(13) -0.0020(11) C5 0.0279(17) 0.0420(19) 0.0360(18) 0.0004(12) 0.0044(14) -0.0069(12) C6 0.0204(12) 0.0282(14) 0.0261(13) -0.0001(11) 0.0036(10) 0.0045(10) C7 0.0287(15) 0.0411(18) 0.0273(15) -0.0018(13) 0.0042(12) -0.0039(12) _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 2.658(3) 2 ? Pb1 N1 2.658(3) . ? Pb1 Cl1 2.8113(8) . ? Pb1 Cl1 2.8113(8) 2 ? Pb1 Cl1 2.9256(8) 2_545 ? Pb1 Cl1 2.9256(8) 1_545 ? Cl1 Pb1 2.9256(8) 1_565 ? N1 C5 1.331(5) . ? N1 C1 1.343(4) . ? N2 C6 1.291(4) . ? N2 N2 1.405(5) 3_665 ? C1 C2 1.375(4) . ? C1 H1A 0.9300 . ? C2 C3 1.391(4) . ? C2 H2A 0.9300 . ? C3 C4 1.386(4) . ? C3 C6 1.494(3) . ? C4 C5 1.386(5) . ? C4 H4A 0.9300 . ? C5 H5A 0.9300 . ? C6 C7 1.499(4) . ? C7 H7D 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 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 N1 Pb1 N1 167.21(10) 2 . ? N1 Pb1 Cl1 84.12(6) 2 . ? N1 Pb1 Cl1 86.92(6) . . ? N1 Pb1 Cl1 86.92(6) 2 2 ? N1 Pb1 Cl1 84.12(6) . 2 ? Cl1 Pb1 Cl1 91.06(3) . 2 ? N1 Pb1 Cl1 96.00(6) 2 2_545 ? N1 Pb1 Cl1 93.31(6) . 2_545 ? Cl1 Pb1 Cl1 177.764(19) . 2_545 ? Cl1 Pb1 Cl1 91.18(2) 2 2_545 ? N1 Pb1 Cl1 93.31(6) 2 1_545 ? N1 Pb1 Cl1 96.00(6) . 1_545 ? Cl1 Pb1 Cl1 91.18(2) . 1_545 ? Cl1 Pb1 Cl1 177.764(19) 2 1_545 ? Cl1 Pb1 Cl1 86.59(3) 2_545 1_545 ? Pb1 Cl1 Pb1 91.18(2) . 1_565 ? C5 N1 C1 117.2(3) . . ? C5 N1 Pb1 117.4(2) . . ? C1 N1 Pb1 124.7(2) . . ? C6 N2 N2 113.7(3) . 3_665 ? N1 C1 C2 123.2(3) . . ? N1 C1 H1A 118.4 . . ? C2 C1 H1A 118.4 . . ? C1 C2 C3 119.7(3) . . ? C1 C2 H2A 120.2 . . ? C3 C2 H2A 120.2 . . ? C4 C3 C2 117.2(2) . . ? C4 C3 C6 121.4(3) . . ? C2 C3 C6 121.4(2) . . ? C5 C4 C3 119.4(3) . . ? C5 C4 H4A 120.3 . . ? C3 C4 H4A 120.3 . . ? N1 C5 C4 123.3(3) . . ? N1 C5 H5A 118.3 . . ? C4 C5 H5A 118.3 . . ? N2 C6 C3 114.9(2) . . ? N2 C6 C7 126.2(2) . . ? C3 C6 C7 118.9(2) . . ? C6 C7 H7D 109.5 . . ? C6 C7 H7A 109.5 . . ? H7D C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7D C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? 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 N1 Pb1 Cl1 Pb1 -86.80(6) 2 . . 1_565 ? N1 Pb1 Cl1 Pb1 84.05(6) . . . 1_565 ? Cl1 Pb1 Cl1 Pb1 0.0 2 . . 1_565 ? Cl1 Pb1 Cl1 Pb1 180.000(3) 2_545 . . 1_565 ? Cl1 Pb1 Cl1 Pb1 180.0 1_545 . . 1_565 ? N1 Pb1 N1 C5 -110.3(2) 2 . . . ? Cl1 Pb1 N1 C5 -155.9(2) . . . . ? Cl1 Pb1 N1 C5 -64.5(2) 2 . . . ? Cl1 Pb1 N1 C5 26.3(2) 2_545 . . . ? Cl1 Pb1 N1 C5 113.2(2) 1_545 . . . ? N1 Pb1 N1 C1 59.7(2) 2 . . . ? Cl1 Pb1 N1 C1 14.1(2) . . . . ? Cl1 Pb1 N1 C1 105.5(2) 2 . . . ? Cl1 Pb1 N1 C1 -163.7(2) 2_545 . . . ? Cl1 Pb1 N1 C1 -76.8(2) 1_545 . . . ? C5 N1 C1 C2 0.6(5) . . . . ? Pb1 N1 C1 C2 -169.4(2) . . . . ? N1 C1 C2 C3 0.1(5) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C1 C2 C3 C6 177.9(3) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C6 C3 C4 C5 -178.2(3) . . . . ? C1 N1 C5 C4 -1.0(5) . . . . ? Pb1 N1 C5 C4 169.8(2) . . . . ? C3 C4 C5 N1 0.5(5) . . . . ? N2 N2 C6 C3 -179.1(3) 3_665 . . . ? N2 N2 C6 C7 -0.2(5) 3_665 . . . ? C4 C3 C6 N2 174.6(3) . . . . ? C2 C3 C6 N2 -3.9(4) . . . . ? C4 C3 C6 C7 -4.4(4) . . . . ? C2 C3 C6 C7 177.2(3) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.133 _refine_diff_density_min -0.763 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 932819'