# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Michel Giffard' _publ_contact_author_email MICHEL.GIFFARD@UNIV-ANGERS.FR _publ_section_title ; Polymorphism of lead (II) benzenethiolate: a noncentrosymmetric new allotropic form of Pb(SPh)2 ; loop_ _publ_author_name 'Michel Giffard' 'Benoit Gravoueille' 'Jerome Luc' 'Nicolas Mercier' 'Emilie Ripaud' 'Bouchta Sahraoui' #------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------# data_new _database_code_depnum_ccdc_archive 'CCDC 670193' _audit_creation_date 2007-10-08T18:16:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_sum 'C12 H10 Pb S2' _chemical_formula_weight 425.54 _chemical_absolute_configuration ad #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 c a' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, y, -z+1/2' 'x+1/2, -y, -z' 'x, -y, z+1/2' _cell_length_a 27.1492(11) _cell_length_b 6.0119(2) _cell_length_c 7.2935(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1190.43(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 2.374 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 14.485 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.103 _exptl_absorpt_correction_T_max 0.282 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 10365 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.39 _diffrn_reflns_theta_max 27.52 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measured_fraction_theta_full 0.998 _reflns_number_total 2205 _reflns_number_gt 1822 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0032P)^2^+0.6566P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr. _refine_ls_extinction_method none _refine_ls_number_reflns 2205 _refine_ls_number_parameters 136 _refine_ls_number_restraints 1 _refine_ls_R_factor_gt 0.027 _refine_ls_wR_factor_ref 0.0454 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.123(8) _refine_diff_density_max 0.72 _refine_diff_density_min -0.849 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pb Pb -3.394 10.111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.125 0.123 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly S2 S 0.47586(6) 0.5847(3) 0.0081(2) 0.0321(4) Uani 1 d . . . C1 C 0.3145(3) 0.7407(14) -0.2903(10) 0.0329(18) Uani 1 d . . . C2 C 0.2835(3) 0.5695(14) -0.2372(9) 0.0370(18) Uani 1 d . . . H2 H 0.296 0.4502 -0.1707 0.044 Uiso 1 calc R . . C12 C 0.5171(3) 0.1835(13) 0.1177(12) 0.032(2) Uani 1 d . . . H12 H 0.4853 0.1368 0.1458 0.039 Uiso 1 calc R . . C6 C 0.2946(4) 0.9165(17) -0.3868(13) 0.039(2) Uani 1 d . . . H6 H 0.3151 1.0323 -0.423 0.047 Uiso 1 calc R . . C5 C 0.2451(4) 0.9259(17) -0.4313(11) 0.047(3) Uani 1 d . . . H5 H 0.2325 1.0461 -0.4967 0.057 Uiso 1 calc R . . C11 C 0.5568(3) 0.0410(15) 0.1496(11) 0.038(2) Uani 1 d . . . H11 H 0.5516 -0.0994 0.1993 0.046 Uiso 1 calc R . . C10 C 0.6032(4) 0.1096(18) 0.1072(13) 0.043(3) Uani 1 d . . . H10 H 0.6298 0.0161 0.1307 0.052 Uiso 1 calc R . . C4 C 0.2147(3) 0.755(2) -0.3776(12) 0.044(2) Uani 1 d . . . H4 H 0.1813 0.7607 -0.4048 0.053 Uiso 1 calc R . . C7 C 0.5245(2) 0.3935(11) 0.0446(8) 0.0283(16) Uani 1 d . . . C9 C 0.6114(3) 0.3153(15) 0.0302(13) 0.046(2) Uani 1 d . . . H9 H 0.6433 0.3579 -0.0007 0.055 Uiso 1 calc R . . C8 C 0.5723(3) 0.4602(12) -0.0017(8) 0.0339(17) Uani 1 d . . . H8 H 0.5779 0.5995 -0.0531 0.041 Uiso 1 calc R . . C3 C 0.2339(3) 0.5746(14) -0.2825(9) 0.0433(19) Uani 1 d . . . H3 H 0.2134 0.4572 -0.2493 0.052 Uiso 1 calc R . . S1 S 0.37755(8) 0.7488(4) -0.2324(3) 0.0539(6) Uani 1 d . . . Pb Pb 0.412419(18) 0.34159(4) -0.18456(3) 0.03837(8) Uani 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 S2 0.0337(9) 0.0327(9) 0.0298(9) 0.0019(7) -0.0015(7) -0.0026(8) C1 0.033(4) 0.037(5) 0.029(4) -0.004(4) 0.007(4) 0.007(4) C2 0.034(4) 0.047(5) 0.030(4) 0.005(3) -0.004(3) 0.006(4) C12 0.036(5) 0.037(6) 0.024(4) -0.005(4) 0.008(4) -0.005(4) C6 0.040(6) 0.033(5) 0.046(5) 0.003(5) 0.006(5) -0.005(5) C5 0.061(7) 0.042(5) 0.038(6) 0.004(4) -0.005(5) 0.012(6) C11 0.045(6) 0.035(5) 0.034(5) -0.008(4) -0.002(4) 0.002(5) C10 0.041(6) 0.048(6) 0.041(5) -0.010(5) -0.002(4) 0.006(5) C4 0.029(5) 0.058(6) 0.046(6) -0.007(6) -0.008(4) 0.007(5) C7 0.028(4) 0.039(5) 0.018(3) -0.006(3) -0.001(3) -0.003(3) C9 0.028(4) 0.057(6) 0.052(6) -0.001(4) 0.001(4) -0.003(4) C8 0.039(4) 0.035(4) 0.028(4) -0.005(3) 0.005(3) -0.008(4) C3 0.045(5) 0.043(5) 0.042(5) 0.002(4) 0.000(4) -0.006(4) S1 0.0317(11) 0.0352(11) 0.0947(17) -0.0053(11) -0.0024(11) 0.0039(10) Pb 0.03423(12) 0.03164(13) 0.04925(14) -0.00260(12) -0.0014(3) -0.0035(2) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 S2 C7 1.770(7) . ? S2 Pb 2.6604(18) . ? S2 Pb 2.8614(17) 4_565 ? C1 C6 1.380(12) . ? C1 C2 1.385(11) . ? C1 S1 1.764(8) . ? C2 C3 1.388(10) . ? C12 C7 1.385(10) . ? C12 C11 1.396(11) . ? C6 C5 1.385(13) . ? C5 C4 1.373(14) . ? C11 C10 1.362(13) . ? C10 C9 1.377(13) . ? C4 C3 1.390(13) . ? C7 C8 1.401(9) . ? C9 C8 1.393(11) . ? S1 Pb 2.648(2) . ? Pb S2 2.8614(17) 4_564 ? 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 C7 S2 Pb 101.8(2) . . ? C7 S2 Pb 115.6(2) . 4_565 ? Pb S2 Pb 96.26(6) . 4_565 ? C6 C1 C2 118.3(8) . . ? C6 C1 S1 118.7(7) . . ? C2 C1 S1 122.9(6) . . ? C1 C2 C3 120.5(7) . . ? C7 C12 C11 120.8(8) . . ? C1 C6 C5 122.1(9) . . ? C4 C5 C6 119.1(9) . . ? C10 C11 C12 119.4(9) . . ? C11 C10 C9 121.0(10) . . ? C5 C4 C3 120.1(8) . . ? C12 C7 C8 119.2(7) . . ? C12 C7 S2 122.8(6) . . ? C8 C7 S2 118.0(5) . . ? C10 C9 C8 120.4(8) . . ? C9 C8 C7 119.2(7) . . ? C4 C3 C2 120.0(8) . . ? C1 S1 Pb 110.7(3) . . ? S1 Pb S2 78.06(6) . . ? S1 Pb S2 88.21(6) . 4_564 ? S2 Pb S2 86.50(5) . 4_564 ? # Attachment 'alpha_Pb_SPh_2.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2007-10-08 at 18:10:05 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\cifdoc.dat # CIF files read : sad #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_sad _database_code_depnum_ccdc_archive 'CCDC 684203' _audit_creation_date 2007-10-08T18:10:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_sum 'C12 H10 Pb S2' _chemical_formula_weight 425.51 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P m c n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y, z' 'x, -y-1/2, z-1/2' _cell_length_a 27.0798(13) _cell_length_b 5.7437(3) _cell_length_c 7.452(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1159.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 2.439 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 14.88 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.113 _exptl_absorpt_correction_T_max 0.300 #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 11520 _diffrn_reflns_av_R_equivalents 0.0632 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 4.21 _diffrn_reflns_theta_max 29 _diffrn_reflns_theta_full 29 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 1558 _reflns_number_gt 987 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #------------------ REFINEMENT INFORMATION ----------------------------------# _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^)+(0.0246P)^2^+1.1217P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr. _refine_ls_extinction_method none _refine_ls_number_reflns 1558 _refine_ls_number_parameters 79 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0627 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0 _refine_diff_density_max 1.066 _refine_diff_density_min -1.816 #------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_group _atom_site_disorder_assembly Pb Pb 0.75 0.40174(5) 0.41178(4) 0.04471(14) Uani 1 d S . . S1A S 0.69382(9) 0.1540(4) 0.2130(3) 0.0271(6) Uani 0.5 d P . . C2 C 0.6490(2) 0.5400(11) 0.0741(7) 0.0473(16) Uani 1 d . . . H004 H 0.6815 0.5703 0.0409 0.057 Uiso 1 calc R . . C6 C 0.5905(3) 0.2949(11) 0.2087(7) 0.0532(17) Uani 1 d . . . H005 H 0.5822 0.1574 0.2672 0.064 Uiso 1 calc R . . C1 C 0.6385(3) 0.3346(10) 0.1620(7) 0.0465(16) Uani 1 d . . . C3 C 0.61349(19) 0.7006(10) 0.0341(7) 0.0360(13) Uani 1 d . . . H007 H 0.6219 0.8366 -0.0264 0.043 Uiso 1 calc R . . C4 C 0.5656(2) 0.6606(10) 0.0832(7) 0.0417(14) Uani 1 d . . . H008 H 0.5413 0.77 0.058 0.05 Uiso 1 calc R . . C5 C 0.5538(2) 0.4559(13) 0.1705(8) 0.0526(18) Uani 1 d . . . H009 H 0.5213 0.4262 0.2036 0.063 Uiso 1 calc R . . S1B S 0.70957(10) -0.0373(5) 0.4862(4) 0.0400(7) Uani 0.5 d P . . 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 Pb 0.0698(3) 0.03020(18) 0.03411(18) 0.00041(16) 0 0 S1A 0.0275(13) 0.0303(14) 0.0234(12) 0.0023(10) 0.0019(10) -0.0027(11) C2 0.031(3) 0.069(4) 0.042(3) 0.018(3) 0.010(3) 0.011(3) C6 0.092(5) 0.038(3) 0.030(3) 0.003(3) 0.000(3) -0.020(4) C1 0.071(5) 0.044(4) 0.024(3) 0.007(3) 0.012(3) 0.018(3) C3 0.038(3) 0.029(3) 0.041(3) 0.006(3) -0.003(2) 0.003(3) C4 0.035(3) 0.056(4) 0.034(3) -0.007(3) -0.004(3) 0.015(3) C5 0.041(4) 0.082(6) 0.035(3) -0.006(3) 0.006(3) -0.024(4) S1B 0.0234(14) 0.0309(16) 0.0657(18) 0.0041(14) 0.0022(14) -0.0016(12) #------------------ MOLECULAR GEOMETRY --------------------------------------# _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 Pb S1A 2.556(2) . ? Pb S1A 2.556(2) 7_755 ? Pb S1A 2.730(2) 2_655 ? Pb S1A 2.730(2) 8_566 ? Pb S1B 2.805(3) . ? Pb S1B 2.805(3) 7_755 ? S1A C1 1.860(6) . ? S1A S1B 2.353(4) . ? S1A Pb 2.730(2) 2_654 ? C2 C3 1.366(7) . ? C2 C1 1.378(8) . ? C2 S1B 1.766(6) 8_565 ? C6 C1 1.367(9) . ? C6 C5 1.386(9) . ? C3 C4 1.366(7) . ? C4 C5 1.381(8) . ? S1B C2 1.766(6) 8_566 ? S1B S1B 2.190(6) 7_755 ? 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 S1A Pb S1A 73.05(11) . 7_755 ? S1A Pb S1A 137.97(4) . 2_655 ? S1A Pb S1A 94.56(7) 7_755 2_655 ? S1A Pb S1A 94.56(7) . 8_566 ? S1A Pb S1A 137.97(4) 7_755 8_566 ? S1A Pb S1A 67.73(10) 2_655 8_566 ? S1A Pb S1B 51.81(8) . . ? S1A Pb S1B 81.17(8) 7_755 . ? S1A Pb S1B 87.11(8) 2_655 . ? S1A Pb S1B 60.95(8) 8_566 . ? S1A Pb S1B 81.17(8) . 7_755 ? S1A Pb S1B 51.81(8) 7_755 7_755 ? S1A Pb S1B 60.95(8) 2_655 7_755 ? S1A Pb S1B 87.11(8) 8_566 7_755 ? S1B Pb S1B 45.96(11) . 7_755 ? C1 S1A S1B 125.7(2) . . ? C1 S1A Pb 106.7(2) . . ? S1B S1A Pb 69.55(9) . . ? C1 S1A Pb 110.23(19) . 2_654 ? S1B S1A Pb 123.76(12) . 2_654 ? Pb S1A Pb 102.13(8) . 2_654 ? C3 C2 C1 122.5(5) . . ? C3 C2 S1B 125.4(5) . 8_565 ? C1 C2 S1B 111.1(4) . 8_565 ? C1 C6 C5 121.2(6) . . ? C6 C1 C2 117.3(6) . . ? C6 C1 S1A 128.4(5) . . ? C2 C1 S1A 114.1(5) . . ? C2 C3 C4 119.7(5) . . ? C3 C4 C5 119.3(5) . . ? C4 C5 C6 119.9(5) . . ? C2 S1B S1B 158.2(2) 8_566 7_755 ? C2 S1B S1A 99.0(2) 8_566 . ? S1B S1B S1A 100.44(9) 7_755 . ? C2 S1B Pb 116.3(2) 8_566 . ? S1B S1B Pb 67.02(6) 7_755 . ? S1A S1B Pb 58.64(9) . . ?