# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_coden_Cambridge 177 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Philippe Leriche' 'David Aillerie' 'Magali Allain' 'Antonio Cravino' 'Pierre Frere' 'J Roncali' 'Sophie Roquet' _publ_contact_author_name 'Philippe Leriche' _publ_contact_author_email PHILIPPE.LERICHE@UNIV-ANGERS.FR _publ_section_title ; 3D-Conjugated Systems Based on Oligothiophenes and Phosphorus Nodes ; # Attachment '6a.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2006-01-19 at 14:47:59 # 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 : pld041 struct #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_pld041 _database_code_depnum_ccdc_archive 'CCDC 684727' _audit_creation_date 2006-01-19T14:47:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C12 H6 Br3 P1 S3' _chemical_formula_sum 'C12 H6 Br3 P S3' _chemical_formula_weight 517.05 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.563(1) _cell_length_b 9.483(1) _cell_length_c 18.527(3) _cell_angle_alpha 90 _cell_angle_beta 101.93(1) _cell_angle_gamma 90 _cell_volume 1643.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 191 _cell_measurement_theta_min 5 _cell_measurement_theta_max 22 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_diffrn 2.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 7.823 _exptl_absorpt_correction_type multi-scan(Sadabs) _exptl_absorpt_correction_T_min 0.101 _exptl_absorpt_correction_T_max 0.334 _exptl_absorpt_process_details ; '(SADABS (Sheldrick, Bruker, 2000))' ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_probe x-ray _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 27411 _diffrn_reflns_av_R_equivalents 0.0587 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _reflns_number_total 2887 _reflns_number_gt 2162 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'EvalCCD (Duisenberg & Schreurs 1990-2000)' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.1 (Crystal Impact gbr 2005)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ 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^)+(0.0402P)^2^+4.6762P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2887 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0404 _refine_ls_wR_factor_ref 0.096 _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 1.305 _refine_diff_density_min -0.826 #------------------ 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' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 '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 C01 C 0.5369(5) 0.1127(5) 0.7513(3) 0.0323(12) Uani 1 d . . . C02 C 0.5040(6) -0.0077(6) 0.7845(3) 0.0451(14) Uani 1 d . . . H02 H 0.4596 -0.0849 0.7584 0.054 Uiso 1 calc R . . C03 C 0.5439(7) -0.0037(7) 0.8627(3) 0.0497(15) Uani 1 d . . . H03 H 0.5297 -0.0779 0.8933 0.06 Uiso 1 calc R . . C04 C 0.6044(6) 0.1191(6) 0.8872(3) 0.0403(14) Uani 1 d . . . C05 C 0.6765(6) 0.1144(6) 0.6304(3) 0.0399(13) Uani 1 d . . . C06 C 0.6986(7) 0.0839(8) 0.5604(3) 0.063(2) Uani 1 d . . . H06 H 0.6245 0.071 0.5197 0.076 Uiso 1 calc R . . C07 C 0.8439(7) 0.0742(8) 0.5567(3) 0.0575(18) Uani 1 d . . . H07 H 0.8765 0.0559 0.5137 0.069 Uiso 1 calc R . . C08 C 0.9287(6) 0.0944(6) 0.6223(3) 0.0362(13) Uani 1 d . . . C09 C 0.4888(5) 0.3307(6) 0.6444(3) 0.0351(12) Uani 1 d . . . C10 C 0.5619(6) 0.4258(6) 0.6093(3) 0.0456(15) Uani 1 d . . . H10 H 0.6427 0.4013 0.5915 0.055 Uiso 1 calc R . . C11 C 0.5048(7) 0.5608(7) 0.6027(4) 0.0583(18) Uani 1 d . . . H11 H 0.5417 0.6349 0.5796 0.07 Uiso 1 calc R . . C12 C 0.3908(6) 0.5721(6) 0.6334(3) 0.0441(14) Uani 1 d . . . P01 P 0.50299(14) 0.13967(16) 0.65255(8) 0.0355(3) Uani 1 d . . . S01 S 0.61646(16) 0.23444(15) 0.81684(7) 0.0408(3) Uani 1 d . . . S02 S 0.83795(14) 0.12706(15) 0.69123(7) 0.0367(3) Uani 1 d . . . S03 S 0.34833(16) 0.41673(16) 0.67046(8) 0.0439(4) Uani 1 d . . . Br01 Br 0.66917(9) 0.17279(9) 0.98545(4) 0.0707(2) Uani 1 d . . . Br02 Br 1.12943(6) 0.08496(7) 0.64279(3) 0.04754(19) Uani 1 d . . . Br03 Br 0.27988(8) 0.73432(7) 0.63850(4) 0.0643(2) 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 C01 0.030(3) 0.033(3) 0.034(3) -0.002(2) 0.007(2) 0.001(2) C02 0.043(3) 0.039(3) 0.052(4) 0.002(3) 0.009(3) -0.003(3) C03 0.059(4) 0.042(4) 0.050(4) 0.013(3) 0.017(3) 0.003(3) C04 0.046(3) 0.046(4) 0.031(3) 0.007(3) 0.014(3) 0.011(3) C05 0.037(3) 0.048(3) 0.034(3) -0.008(3) 0.004(2) 0.005(3) C06 0.047(4) 0.111(6) 0.031(3) -0.020(4) 0.003(3) 0.009(4) C07 0.050(4) 0.092(5) 0.033(3) -0.013(3) 0.015(3) 0.006(4) C08 0.036(3) 0.037(3) 0.038(3) 0.002(2) 0.014(2) 0.003(2) C09 0.031(3) 0.041(3) 0.032(3) 0.003(2) 0.002(2) 0.002(2) C10 0.033(3) 0.056(4) 0.050(4) 0.009(3) 0.014(3) 0.002(3) C11 0.050(4) 0.059(5) 0.066(4) 0.015(4) 0.011(3) -0.011(3) C12 0.046(4) 0.040(3) 0.039(3) 0.001(3) -0.008(3) 0.002(3) P01 0.0302(7) 0.0425(8) 0.0320(7) -0.0059(6) 0.0023(6) 0.0012(6) S01 0.0520(9) 0.0367(8) 0.0334(7) -0.0020(6) 0.0084(6) -0.0038(7) S02 0.0348(7) 0.0467(8) 0.0287(7) -0.0030(6) 0.0070(6) 0.0039(6) S03 0.0477(9) 0.0415(8) 0.0451(8) 0.0011(7) 0.0159(7) 0.0040(7) Br01 0.0849(5) 0.0945(6) 0.0320(3) -0.0010(3) 0.0104(3) 0.0028(4) Br02 0.0379(3) 0.0536(4) 0.0537(4) 0.0082(3) 0.0155(3) 0.0053(3) Br03 0.0672(5) 0.0443(4) 0.0760(5) -0.0003(3) 0.0021(4) 0.0084(3) #------------------ 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 C01 C02 1.364(8) . ? C01 S01 1.733(5) . ? C01 P01 1.809(5) . ? C02 C03 1.421(8) . ? C03 C04 1.338(9) . ? C04 S01 1.724(5) . ? C04 Br01 1.867(6) . ? C05 C06 1.388(8) . ? C05 S02 1.717(5) . ? C05 P01 1.806(5) . ? C06 C07 1.408(9) . ? C07 C08 1.328(8) . ? C08 S02 1.715(5) . ? C08 Br02 1.880(5) . ? C09 C10 1.384(8) . ? C09 S03 1.723(5) . ? C09 P01 1.821(6) . ? C10 C11 1.387(9) . ? C11 C12 1.334(8) . ? C12 S03 1.709(6) . ? C12 Br03 1.882(6) . ? 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 C02 C01 S01 110.5(4) . . ? C02 C01 P01 124.4(4) . . ? S01 C01 P01 125.1(3) . . ? C01 C02 C03 113.5(5) . . ? C04 C03 C02 112.1(5) . . ? C03 C04 S01 112.8(4) . . ? C03 C04 Br01 127.0(4) . . ? S01 C04 Br01 120.2(3) . . ? C06 C05 S02 109.8(4) . . ? C06 C05 P01 124.4(4) . . ? S02 C05 P01 125.8(3) . . ? C05 C06 C07 113.7(5) . . ? C08 C07 C06 111.6(5) . . ? C07 C08 S02 113.6(4) . . ? C07 C08 Br02 125.6(4) . . ? S02 C08 Br02 120.7(3) . . ? C10 C09 S03 108.8(4) . . ? C10 C09 P01 130.6(4) . . ? S03 C09 P01 119.8(3) . . ? C09 C10 C11 114.5(5) . . ? C12 C11 C10 112.2(6) . . ? C11 C12 S03 112.6(5) . . ? C11 C12 Br03 127.3(5) . . ? S03 C12 Br03 120.1(3) . . ? C05 P01 C01 103.3(2) . . ? C05 P01 C09 99.8(3) . . ? C01 P01 C09 102.7(2) . . ? C04 S01 C01 91.1(3) . . ? C08 S02 C05 91.4(3) . . ? C12 S03 C09 91.8(3) . . ? # Attachment '6b.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2005-09-21 at 18:09:06 # 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 : lph668 #------------------ SECTION 1. GLOBAL INFORMATION ---------------------------# data_lph668 _database_code_depnum_ccdc_archive 'CCDC 684728' _audit_creation_date 2005-09-21T18:09:06-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_formula_moiety 'C12 H6 Br3 O1 P1 S3' _chemical_formula_sum 'C12 H6 Br3 O P S3' _chemical_formula_weight 533.05 #------------------ UNIT CELL INFORMATION -----------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8214(9) _cell_length_b 9.4798(8) _cell_length_c 18.488(2) _cell_angle_alpha 90 _cell_angle_beta 102.87(1) _cell_angle_gamma 90 _cell_volume 1678.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 25.8 #------------------ CRYSTAL INFORMATION -------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.13 _exptl_crystal_density_diffrn 2.11 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 7.671 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.1043 _exptl_absorpt_correction_T_max 0.3758 _exptl_absorpt_process_details ; PLATON-ABSGAUSS : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13 ; #------------------ DATA COLLECTION INFORMATION -----------------------------# _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'STOE IPDS' _diffrn_measurement_method 'Oscillation Phi Incr 1.3 deg' _diffrn_detector_area_resol_mean 6.66 _diffrn_reflns_number 13628 _diffrn_reflns_av_R_equivalents 0.0804 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 25.89 _diffrn_reflns_theta_full 25.89 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _reflns_number_total 3243 _reflns_number_gt 2192 _reflns_threshold_expression >2sigma(I) #------------------ COMPUTER PROGRAMS USED ----------------------------------# _computing_data_collection 'EXPOSE, STOE IPDS' _computing_cell_refinement 'SELECT,CELL, STOE IPDS' _computing_data_reduction 'INTEGRATE, STOE IPDS' _computing_structure_solution 'Direct methods (Sir92,Altomare et al.,1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'DIAMOND 3.0e (Crystal Impact GbR 2004)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #------------------ 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^)+(0.0967P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3243 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1546 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _refine_diff_density_max 1.512 _refine_diff_density_min -1.339 #------------------ 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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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' Br Br -0.2901 2.4595 '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 C01 C 0.5421(7) 0.1177(7) 0.7528(3) 0.0398(14) Uani 1 d . . . C02 C 0.5112(8) -0.0033(7) 0.7854(4) 0.0489(17) Uani 1 d . . . H02 H 0.4688 -0.0803 0.7582 0.059 Uiso 1 calc R . . C03 C 0.5483(9) -0.0027(9) 0.8634(4) 0.062(2) Uani 1 d . . . H03 H 0.5316 -0.0767 0.8932 0.075 Uiso 1 calc R . . C04 C 0.6104(9) 0.1174(9) 0.8887(4) 0.0561(19) Uani 1 d . . . C05 C 0.6740(7) 0.1204(8) 0.6293(4) 0.0438(15) Uani 1 d . . . C06 C 0.6865(8) 0.0863(11) 0.5593(4) 0.066(2) Uani 1 d . . . H06 H 0.6105 0.073 0.5197 0.08 Uiso 1 calc R . . C07 C 0.8272(8) 0.0733(9) 0.5531(4) 0.057(2) Uani 1 d . . . H07 H 0.854 0.0526 0.5091 0.069 Uiso 1 calc R . . C08 C 0.9173(7) 0.0943(7) 0.6182(4) 0.0423(15) Uani 1 d . . . C09 C 0.4877(7) 0.3377(7) 0.6457(4) 0.0419(15) Uani 1 d . . . C10 C 0.5541(7) 0.4341(9) 0.6106(4) 0.0558(19) Uani 1 d . . . H10 H 0.6318 0.4124 0.5917 0.067 Uiso 1 calc R . . C11 C 0.4935(9) 0.5697(9) 0.6058(5) 0.067(2) Uani 1 d . . . H11 H 0.5265 0.6464 0.5835 0.081 Uiso 1 calc R . . C12 C 0.3845(8) 0.5751(8) 0.6367(4) 0.0536(18) Uani 1 d . . . O01 O 0.3990(5) 0.0645(5) 0.6129(3) 0.0527(12) Uani 1 d . . . P01 P 0.51363(17) 0.15149(19) 0.65605(9) 0.0379(4) Uani 1 d . . . S01 S 0.6226(2) 0.2351(2) 0.81976(10) 0.0527(5) Uani 1 d . . . S02 S 0.83565(16) 0.1314(2) 0.68904(9) 0.0420(4) Uani 1 d . . . S03 S 0.3500(2) 0.4171(2) 0.67354(10) 0.0504(4) Uani 1 d . . . Br01 Br 0.67873(14) 0.16868(14) 0.98715(5) 0.0970(4) Uani 1 d . . . Br02 Br 1.11125(7) 0.08464(8) 0.63463(4) 0.0512(2) Uani 1 d . . . Br03 Br 0.27060(11) 0.73193(10) 0.64297(6) 0.0795(3) 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 C01 0.039(3) 0.043(4) 0.038(3) -0.005(3) 0.010(3) 0.005(3) C02 0.055(4) 0.039(4) 0.054(4) 0.005(3) 0.016(3) -0.001(3) C03 0.081(6) 0.052(5) 0.057(4) 0.013(4) 0.019(4) 0.012(4) C04 0.063(5) 0.066(5) 0.041(4) 0.003(3) 0.016(3) 0.013(4) C05 0.038(3) 0.054(4) 0.038(3) -0.008(3) 0.006(3) 0.000(3) C06 0.045(4) 0.115(8) 0.038(4) -0.018(4) 0.006(3) 0.000(5) C07 0.049(4) 0.083(6) 0.042(4) -0.009(4) 0.016(3) 0.007(4) C08 0.047(4) 0.041(4) 0.043(3) 0.002(3) 0.016(3) 0.003(3) C09 0.040(3) 0.046(4) 0.036(3) 0.003(3) 0.002(3) 0.001(3) C10 0.038(3) 0.070(5) 0.062(4) 0.019(4) 0.015(3) -0.006(4) C11 0.063(5) 0.056(5) 0.081(6) 0.022(4) 0.012(4) -0.010(4) C12 0.058(4) 0.046(4) 0.049(4) 0.004(3) -0.005(3) -0.005(4) O01 0.040(3) 0.058(3) 0.055(3) -0.009(2) 0.000(2) -0.003(2) P01 0.0318(8) 0.0455(10) 0.0349(8) -0.0029(7) 0.0045(6) -0.0004(7) S01 0.0663(11) 0.0487(10) 0.0404(9) -0.0057(8) 0.0061(8) -0.0027(9) S02 0.0358(8) 0.0549(10) 0.0352(8) -0.0044(7) 0.0077(6) 0.0027(7) S03 0.0579(10) 0.0426(10) 0.0527(10) 0.0027(8) 0.0167(8) 0.0047(9) Br01 0.1278(10) 0.1180(9) 0.0383(4) -0.0054(5) 0.0035(5) 0.0219(7) Br02 0.0401(4) 0.0584(5) 0.0582(4) 0.0067(3) 0.0176(3) 0.0053(3) Br03 0.0890(7) 0.0455(5) 0.0954(7) 0.0006(4) 0.0017(5) 0.0095(5) #------------------ 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 C01 C02 1.360(9) . ? C01 S01 1.721(7) . ? C01 P01 1.777(7) . ? C02 C03 1.407(11) . ? C03 C04 1.326(12) . ? C04 S01 1.718(8) . ? C04 Br01 1.859(8) . ? C05 C06 1.367(10) . ? C05 S02 1.723(7) . ? C05 P01 1.778(7) . ? C06 C07 1.417(10) . ? C07 C08 1.340(10) . ? C08 S02 1.717(6) . ? C08 Br02 1.863(7) . ? C09 C10 1.368(10) . ? C09 S03 1.723(7) . ? C09 P01 1.787(7) . ? C10 C11 1.411(12) . ? C11 C12 1.322(11) . ? C12 S03 1.710(8) . ? C12 Br03 1.879(8) . ? O01 P01 1.477(5) . ? 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 C02 C01 S01 109.8(5) . . ? C02 C01 P01 126.6(5) . . ? S01 C01 P01 123.5(4) . . ? C01 C02 C03 114.7(7) . . ? C04 C03 C02 111.1(7) . . ? C03 C04 S01 113.4(6) . . ? C03 C04 Br01 127.4(6) . . ? S01 C04 Br01 119.1(5) . . ? C06 C05 S02 110.9(5) . . ? C06 C05 P01 125.1(6) . . ? S02 C05 P01 124.0(4) . . ? C05 C06 C07 113.0(7) . . ? C08 C07 C06 112.1(6) . . ? C07 C08 S02 112.9(5) . . ? C07 C08 Br02 125.8(5) . . ? S02 C08 Br02 121.3(4) . . ? C10 C09 S03 109.8(5) . . ? C10 C09 P01 129.7(6) . . ? S03 C09 P01 120.2(4) . . ? C09 C10 C11 113.5(7) . . ? C12 C11 C10 112.3(7) . . ? C11 C12 S03 112.9(6) . . ? C11 C12 Br03 127.5(6) . . ? S03 C12 Br03 119.7(5) . . ? O01 P01 C01 111.9(3) . . ? O01 P01 C05 111.9(3) . . ? C01 P01 C05 107.4(3) . . ? O01 P01 C09 114.8(3) . . ? C01 P01 C09 105.8(3) . . ? C05 P01 C09 104.4(3) . . ? C04 S01 C01 90.9(4) . . ? C08 S02 C05 91.1(3) . . ? C12 S03 C09 91.5(4) . . ?