#Supplementary Material (ESI) for Dalton Transactions #This journal is (C) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 # #------------------------------------------------------------------------- # 1. SUBMISSION DETAILS # _publ_contact_author_name 'Maryse Gouygou' _publ_contact_author_address ; Laboratoire de Chimie de Coordination UPR-CNRS 8241 205, route de Narbonne 31077 Toulouse cedex, France ; _publ_contact_author_phone ' (33) 5 61 33 31 74 ' _publ_contact_author_fax ' (33) 5 61 55 30 03 ' _publ_contact_author_email GOUYGOU@LCC-TOULOUSE.FR #------------------------------------------------------------------------- # 2. TITLE AND AUTHOR LIST _publ_section_title ; Diphosphine Sulfides derived from 2,2'-biphosphole: novel chiral S,S ligands for palladium-catalyzed asymmetric allylic substitution. ; loop_ _publ_author_name _publ_author_address E.Robe ; Laboratoire de Chimie de Coordination UPR-CNRS 8241 205, route de Narbonne 31077 Toulouse cedex, France ; 'Wieslawa Perlikowska' ; Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Lodz, Sienkiewicza 112, Poland ; "C\'eline Lemoine" ; Laboratoire de Chimie de Coordination UPR-CNRS 8241 205, route de Narbonne 31077 Toulouse cedex, France ; 'Lisa Diab' ; Laboratoire de Chimie de Coordination UPR-CNRS 8241 205, route de Narbonne 31077 Toulouse cedex, France ; 'Sandrine Vincendeau' ; Laboratoire de Chimie de Coordination UPR-CNRS 8241 205, route de Narbonne 31077 Toulouse cedex, France ; ; M.Mikolajczyk ; ; Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences, 90-363 Lodz, Sienkiewicza 112, Poland ; 'Jean-Claude Daran' ; Laboratoire de Chimie de Coordination UPR-CNRS 8241 205, route de Narbonne 31077 Toulouse cedex, France ; 'Maryse Gouygou' ; Laboratoire de Chimie de Coordination UPR-CNRS 8241 205, route de Narbonne 31077 Toulouse cedex, France ; #============================================================================== _publ_section_references ; Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. (1999) SIR97- a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. 32, 115-119. Bernardinelli, G. and Flack, H. D. (1985) Acta Crystallogr., Sect A, 41, 500-511. CrysAlis CCD, Oxford Diffraction Ltd., Version 1.170.32 (release 06.06.2003 CrysAlis170 VC++) (compiled Jun 6 2003,13:53:32) CrysAlis RED, Oxford Diffraction Ltd., Version 1.170.32 (release 06.06.2003 CrysAlis170 VC++) (compiled Jun 6 2003,13:53:32) Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565. Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838. Flack, H.D. (1983). Acta Cryst. A39, 876-881. Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure refinement. University of G\"ottingen, Germany. ; #======================================================================== data_wp140606 _database_code_depnum_ccdc_archive 'CCDC 669755' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C40 H36 Cl2 P2 S2' _chemical_formula_sum 'C40 H36 Cl2 P2 S2' _chemical_compound_source 'synthesis as described' _chemical_formula_weight 713.65 _chemical_absolute_configuration ad 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' 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 30.136(2) _cell_length_b 6.5916(4) _cell_length_c 22.9460(13) _cell_angle_alpha 90.000(5) _cell_angle_beta 127.764(8) _cell_angle_gamma 90.000(6) _cell_volume 3603.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 6492 _cell_measurement_theta_max 32.2 _cell_measurement_theta_min 2.8 _exptl_crystal_description box _exptl_crystal_colour colorless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.413 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 'Oxford-Diffraction XCALIBUR' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean 8.2632 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16290 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0285 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 28.28 _reflns_number_total 6325 _reflns_number_gt 5585 _reflns_threshold_expression I>2\s(I) _diffrn_orient_matrix_UB_11 -0.0192518216 _diffrn_orient_matrix_UB_12 0.0126313988 _diffrn_orient_matrix_UB_13 -0.0387820302 _diffrn_orient_matrix_UB_21 0.0226712486 _diffrn_orient_matrix_UB_22 0.0170936114 _diffrn_orient_matrix_UB_23 -0.0011968778 _diffrn_orient_matrix_UB_31 0.0013452874 _diffrn_orient_matrix_UB_32 -0.1054864177 _diffrn_orient_matrix_UB_33 -0.0048481355 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -54.00 60.40 0.8000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 0.0000 0.0000 0.0000 143 #__ type_ start__ end____ width___ exp.time_ 2 omega -54.00 60.40 0.8000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 90.0000 0.0000 0.0000 143 #__ type_ start__ end____ width___ exp.time_ 3 omega -54.00 60.40 0.8000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 180.0000 0.0000 0.0000 143 #__ type_ start__ end____ width___ exp.time_ 4 omega -54.00 60.40 0.8000 20.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 30.0000 -79.0000 270.0000 0.0000 0.0000 143 ; _computing_data_collection ; CrysAlis CCD, Version 1.170.32 (Oxford Diffraction, 2003) ; _computing_cell_refinement ; CrysAlis RED, Version 1.170.32 (Oxford Diffraction, 2003) ; _computing_data_reduction 'CrysAlis RED' _computing_structure_solution 'SIR-97 (Altomare et al., 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0641P)^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 constr _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 0.00(6) _refine_ls_number_reflns 6325 _refine_ls_number_parameters 433 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0991 _refine_ls_wR_factor_gt 0.0962 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.008 _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 C1 C 0.07342(8) 0.1620(4) 0.71888(10) 0.0216(4) Uani 1 1 d . . . H1 H 0.0737 0.3039 0.7345 0.026 Uiso 1 1 calc R . . C2 C -0.02055(8) 0.0157(4) 0.69339(11) 0.0238(5) Uani 1 1 d . . . H2 H -0.0053 -0.1230 0.7134 0.029 Uiso 1 1 calc R . . C3 C 0.01116(9) 0.0969(5) 0.66547(12) 0.0294(5) Uani 1 1 d . . . H3A H -0.0102 0.2156 0.6339 0.035 Uiso 1 1 calc R . . H3B H 0.0086 -0.0087 0.6328 0.035 Uiso 1 1 calc R . . C11 C 0.10555(8) 0.1093(4) 0.86432(11) 0.0219(4) Uani 1 1 d . . . C12 C 0.14765(9) 0.2315(4) 0.91515(12) 0.0265(5) Uani 1 1 d . . . C13 C 0.19429(9) 0.2484(4) 0.90949(12) 0.0252(5) Uani 1 1 d . . . C14 C 0.18741(8) 0.1409(4) 0.85458(11) 0.0224(4) Uani 1 1 d . . . C21 C 0.05211(9) 0.0637(4) 0.84990(11) 0.0234(5) Uani 1 1 d . . . C22 C 0.04112(10) -0.0606(4) 0.88620(12) 0.0280(5) Uani 1 1 d . . . C23 C -0.01999(10) -0.0810(5) 0.85016(13) 0.0319(6) Uani 1 1 d . . . C24 C -0.05430(9) 0.0248(4) 0.78793(12) 0.0259(5) Uani 1 1 d . . . C100 C 0.0000 0.4316(8) 0.5000 0.0509(11) Uani 1 2 d S . . C111 C 0.09845(9) 0.1722(4) 0.67795(11) 0.0272(5) Uani 1 1 d . . . C112 C 0.09741(11) 0.0095(5) 0.63962(14) 0.0377(6) Uani 1 1 d . . . H112 H 0.0809 -0.1148 0.6385 0.045 Uiso 1 1 calc R . . C113 C 0.12047(13) 0.0256(6) 0.60234(16) 0.0509(8) Uani 1 1 d . . . H113 H 0.1191 -0.0870 0.5754 0.061 Uiso 1 1 calc R . . C114 C 0.14512(13) 0.2037(7) 0.60442(17) 0.0547(10) Uani 1 1 d . . . H114 H 0.1613 0.2133 0.5797 0.066 Uiso 1 1 calc R . . C115 C 0.14630(12) 0.3669(6) 0.64207(16) 0.0499(8) Uani 1 1 d . . . H115 H 0.1628 0.4909 0.6429 0.060 Uiso 1 1 calc R . . C116 C 0.12306(10) 0.3510(5) 0.67962(13) 0.0346(6) Uani 1 1 d . . . H116 H 0.1243 0.4641 0.7063 0.042 Uiso 1 1 calc R . . C121 C 0.15044(11) 0.3392(6) 0.97420(15) 0.0461(8) Uani 1 1 d . . . H12A H 0.1151 0.3201 0.9668 0.069 Uiso 1 1 calc R . . H12B H 0.1566 0.4842 0.9724 0.069 Uiso 1 1 calc R . . H12C H 0.1815 0.2842 1.0223 0.069 Uiso 1 1 calc R . . C131 C 0.24414(10) 0.3770(5) 0.96394(14) 0.0355(6) Uani 1 1 d . . . H13A H 0.2352 0.5198 0.9492 0.053 Uiso 1 1 calc R . . H13B H 0.2760 0.3357 0.9654 0.053 Uiso 1 1 calc R . . H13C H 0.2538 0.3599 1.0129 0.053 Uiso 1 1 calc R . . C141 C 0.22802(9) 0.1229(4) 0.83848(12) 0.0252(5) Uani 1 1 d . . . C142 C 0.25519(10) 0.2899(5) 0.83774(15) 0.0368(6) Uani 1 1 d . . . H142 H 0.2467 0.4208 0.8458 0.044 Uiso 1 1 calc R . . C143 C 0.29470(11) 0.2705(6) 0.82544(17) 0.0486(8) Uani 1 1 d . . . H143 H 0.3132 0.3873 0.8254 0.058 Uiso 1 1 calc R . . C144 C 0.30700(12) 0.0839(6) 0.81338(17) 0.0483(8) Uani 1 1 d . . . H144 H 0.3346 0.0702 0.8059 0.058 Uiso 1 1 calc R . . C145 C 0.27948(12) -0.0853(5) 0.81202(17) 0.0465(7) Uani 1 1 d . . . H145 H 0.2874 -0.2152 0.8025 0.056 Uiso 1 1 calc R . . C146 C 0.24012(11) -0.0656(5) 0.82462(14) 0.0343(6) Uani 1 1 d . . . H146 H 0.2213 -0.1825 0.8237 0.041 Uiso 1 1 calc R . . C200 C -0.0094(4) 0.293(2) 1.0244(5) 0.092(3) Uani 0.50 1 d P . . C211 C -0.08208(9) -0.0131(4) 0.62747(12) 0.0260(5) Uani 1 1 d . . . C212 C -0.11828(9) 0.1502(5) 0.59342(12) 0.0338(6) Uani 1 1 d . . . H212 H -0.1047 0.2839 0.6106 0.041 Uiso 1 1 calc R . . C213 C -0.17465(10) 0.1197(6) 0.53407(14) 0.0427(7) Uani 1 1 d . . . H213 H -0.1996 0.2319 0.5122 0.051 Uiso 1 1 calc R . . C214 C -0.19398(11) -0.0730(6) 0.50735(14) 0.0485(8) Uani 1 1 d . . . H214 H -0.2323 -0.0940 0.4667 0.058 Uiso 1 1 calc R . . C215 C -0.15807(13) -0.2344(6) 0.53925(15) 0.0528(9) Uani 1 1 d . . . H215 H -0.1714 -0.3670 0.5201 0.063 Uiso 1 1 calc R . . C216 C -0.10180(11) -0.2055(5) 0.60003(13) 0.0398(6) Uani 1 1 d . . . H216 H -0.0772 -0.3186 0.6224 0.048 Uiso 1 1 calc R . . C221 C 0.08434(11) -0.1697(6) 0.95572(16) 0.0494(8) Uani 1 1 d . . . H22A H 0.1215 -0.1460 0.9685 0.074 Uiso 1 1 calc R . . H22B H 0.0762 -0.3154 0.9489 0.074 Uiso 1 1 calc R . . H22C H 0.0839 -0.1194 0.9955 0.074 Uiso 1 1 calc R . . C223 C -0.03881(11) -0.2182(6) 0.88361(15) 0.0477(8) Uani 1 1 d . . . H22D H -0.0335 -0.3600 0.8762 0.071 Uiso 1 1 calc R . . H22E H -0.0786 -0.1938 0.8599 0.071 Uiso 1 1 calc R . . H22F H -0.0165 -0.1903 0.9365 0.071 Uiso 1 1 calc R . . C241 C -0.11650(9) 0.0328(5) 0.74045(12) 0.0296(5) Uani 1 1 d . . . C242 C -0.14382(10) 0.2163(5) 0.72838(14) 0.0383(6) Uani 1 1 d . . . H242 H -0.1228 0.3370 0.7510 0.046 Uiso 1 1 calc R . . C243 C -0.20244(11) 0.2213(6) 0.68265(15) 0.0484(8) Uani 1 1 d . . . H243 H -0.2213 0.3462 0.6743 0.058 Uiso 1 1 calc R . . C244 C -0.23303(11) 0.0474(7) 0.64966(15) 0.0526(10) Uani 1 1 d . . . H244 H -0.2729 0.0523 0.6187 0.063 Uiso 1 1 calc R . . C245 C -0.20658(11) -0.1308(6) 0.66118(15) 0.0498(8) Uani 1 1 d . . . H245 H -0.2281 -0.2503 0.6378 0.060 Uiso 1 1 calc R . . C246 C -0.14808(10) -0.1414(5) 0.70696(14) 0.0391(6) Uani 1 1 d . . . H246 H -0.1300 -0.2678 0.7151 0.047 Uiso 1 1 calc R . . Cl1 Cl -0.02287(5) 0.58239(19) 0.54043(6) 0.0764(3) Uani 1 1 d . . . Cl2A Cl -0.0554(2) 0.3386(6) 0.9622(3) 0.0852(12) Uani 0.50 1 d P . . Cl2B Cl -0.0640(2) 0.2678(9) 0.9384(3) 0.1201(18) Uani 0.50 1 d P . . P1 P 0.12005(2) 0.01330(9) 0.80421(3) 0.02057(13) Uani 1 1 d . . . P2 P -0.01266(2) 0.15852(9) 0.76818(3) 0.02202(13) Uani 1 1 d . . . S1 S 0.11728(3) -0.28067(10) 0.79644(4) 0.03418(15) Uani 1 1 d . . . S2 S -0.01837(3) 0.45260(10) 0.76017(4) 0.03555(16) 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 C1 0.0176(9) 0.0274(11) 0.0191(9) -0.0006(9) 0.0110(8) -0.0016(9) C2 0.0176(9) 0.0297(12) 0.0211(9) 0.0023(10) 0.0103(8) -0.0017(10) C3 0.0215(10) 0.0440(15) 0.0208(10) -0.0002(10) 0.0120(9) -0.0048(10) C11 0.0195(9) 0.0237(12) 0.0192(9) 0.0022(9) 0.0102(8) 0.0026(9) C12 0.0205(10) 0.0294(12) 0.0238(10) -0.0013(10) 0.0105(8) 0.0009(10) C13 0.0182(9) 0.0232(12) 0.0248(10) 0.0009(9) 0.0084(8) 0.0004(9) C14 0.0165(9) 0.0206(11) 0.0241(10) 0.0016(9) 0.0094(8) 0.0007(9) C21 0.0203(9) 0.0287(13) 0.0198(9) -0.0018(9) 0.0115(8) -0.0002(9) C22 0.0244(11) 0.0334(13) 0.0236(10) 0.0035(10) 0.0134(9) 0.0041(10) C23 0.0278(11) 0.0418(16) 0.0296(11) 0.0036(11) 0.0193(10) -0.0014(11) C24 0.0226(10) 0.0310(13) 0.0273(10) -0.0016(10) 0.0170(9) -0.0016(10) C100 0.059(3) 0.048(3) 0.0338(19) 0.000 0.0226(19) 0.000 C111 0.0182(9) 0.0424(15) 0.0203(9) 0.0004(10) 0.0114(8) -0.0005(10) C112 0.0381(13) 0.0456(17) 0.0347(12) -0.0044(13) 0.0250(11) -0.0005(13) C113 0.0495(16) 0.074(2) 0.0405(15) -0.0113(17) 0.0331(14) 0.0039(18) C114 0.0453(16) 0.092(3) 0.0467(16) -0.0080(18) 0.0383(14) -0.0079(18) C115 0.0481(16) 0.067(2) 0.0473(15) -0.0053(17) 0.0357(14) -0.0181(17) C116 0.0347(12) 0.0431(16) 0.0298(11) -0.0043(12) 0.0217(10) -0.0100(12) C121 0.0363(13) 0.058(2) 0.0419(14) -0.0225(15) 0.0228(12) -0.0077(15) C131 0.0244(11) 0.0332(14) 0.0354(12) -0.0097(12) 0.0114(10) -0.0076(11) C141 0.0171(9) 0.0293(13) 0.0239(10) 0.0023(10) 0.0099(8) 0.0023(9) C142 0.0271(12) 0.0319(14) 0.0513(15) 0.0019(13) 0.0239(11) -0.0011(12) C143 0.0321(14) 0.058(2) 0.0595(18) 0.0077(16) 0.0300(13) -0.0053(14) C144 0.0377(14) 0.062(2) 0.0603(18) 0.0088(17) 0.0376(14) 0.0056(15) C145 0.0476(16) 0.0492(19) 0.0591(17) 0.0011(15) 0.0410(15) 0.0100(15) C146 0.0326(13) 0.0370(15) 0.0410(13) 0.0004(12) 0.0265(11) 0.0019(12) C200 0.086(6) 0.128(10) 0.068(5) -0.031(6) 0.050(5) -0.035(7) C211 0.0212(10) 0.0354(14) 0.0203(9) -0.0013(10) 0.0121(8) -0.0057(10) C212 0.0220(10) 0.0436(16) 0.0274(11) -0.0038(12) 0.0108(9) -0.0039(11) C213 0.0219(11) 0.069(2) 0.0275(11) 0.0035(14) 0.0101(10) 0.0028(13) C214 0.0273(13) 0.078(2) 0.0265(12) -0.0033(14) 0.0093(10) -0.0197(15) C215 0.0469(16) 0.052(2) 0.0311(13) -0.0078(14) 0.0096(12) -0.0275(16) C216 0.0369(13) 0.0408(16) 0.0269(11) -0.0016(12) 0.0120(10) -0.0108(13) C221 0.0308(12) 0.066(2) 0.0447(14) 0.0302(16) 0.0198(12) 0.0127(15) C223 0.0379(14) 0.068(2) 0.0405(14) 0.0187(15) 0.0258(12) -0.0035(15) C241 0.0224(10) 0.0450(16) 0.0233(10) 0.0023(11) 0.0150(9) -0.0014(11) C242 0.0287(12) 0.0502(17) 0.0357(13) 0.0011(13) 0.0196(11) 0.0040(12) C243 0.0308(13) 0.078(2) 0.0385(14) 0.0136(16) 0.0223(12) 0.0181(15) C244 0.0217(12) 0.098(3) 0.0337(13) 0.0142(17) 0.0147(11) -0.0023(16) C245 0.0285(13) 0.073(2) 0.0378(14) 0.0067(16) 0.0149(11) -0.0161(16) C246 0.0300(12) 0.0463(17) 0.0345(12) 0.0087(13) 0.0164(10) -0.0065(13) Cl1 0.0990(7) 0.0647(6) 0.0745(6) -0.0153(5) 0.0577(6) -0.0025(6) Cl2A 0.113(3) 0.0800(19) 0.105(3) -0.0243(17) 0.088(3) -0.0340(17) Cl2B 0.102(2) 0.159(5) 0.098(3) 0.029(3) 0.061(2) 0.015(3) P1 0.0177(2) 0.0213(3) 0.0211(3) -0.0024(2) 0.0110(2) -0.0028(2) P2 0.0179(2) 0.0259(3) 0.0201(2) 0.0016(2) 0.0105(2) -0.0007(2) S1 0.0399(3) 0.0210(3) 0.0440(3) -0.0055(3) 0.0269(3) -0.0051(3) S2 0.0348(3) 0.0257(3) 0.0384(3) 0.0020(3) 0.0185(3) 0.0001(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 C1 C111 1.524(3) . ? C1 C3 1.546(3) . ? C1 P1 1.844(2) . ? C2 C211 1.525(3) . ? C2 C3 1.536(3) . ? C2 P2 1.840(2) . ? C11 C12 1.344(3) . ? C11 C21 1.463(3) . ? C11 P1 1.798(2) . ? C12 C121 1.486(3) . ? C12 C13 1.493(3) . ? C13 C14 1.346(3) . ? C13 C131 1.496(3) . ? C14 C141 1.484(3) . ? C14 P1 1.814(2) . ? C21 C22 1.346(3) . ? C21 P2 1.798(2) . ? C22 C221 1.488(3) . ? C22 C23 1.493(3) . ? C23 C24 1.337(3) . ? C23 C223 1.504(4) . ? C24 C241 1.484(3) . ? C24 P2 1.804(2) . ? C100 Cl1 1.763(3) 2_556 ? C100 Cl1 1.763(3) . ? C111 C112 1.375(4) . ? C111 C116 1.381(4) . ? C112 C113 1.398(4) . ? C113 C114 1.374(5) . ? C114 C115 1.367(5) . ? C115 C116 1.408(3) . ? C141 C142 1.378(4) . ? C141 C146 1.386(4) . ? C142 C143 1.388(4) . ? C143 C144 1.361(5) . ? C144 C145 1.379(5) . ? C145 C146 1.388(3) . ? C200 Cl2A 1.276(12) . ? C200 C200 1.533(17) 2_557 ? C200 Cl2B 1.630(10) . ? C200 Cl2A 1.806(10) 2_557 ? C200 Cl2B 1.826(12) 2_557 ? C211 C216 1.378(4) . ? C211 C212 1.384(4) . ? C212 C213 1.395(3) . ? C213 C214 1.376(5) . ? C214 C215 1.366(5) . ? C215 C216 1.400(4) . ? C241 C246 1.385(4) . ? C241 C242 1.392(4) . ? C242 C243 1.397(4) . ? C243 C244 1.372(5) . ? C244 C245 1.352(5) . ? C245 C246 1.396(4) . ? Cl2A Cl2B 0.640(6) . ? Cl2A C200 1.806(10) 2_557 ? Cl2B C200 1.826(12) 2_557 ? P1 S1 1.9430(9) . ? P2 S2 1.9448(9) . ? 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 C111 C1 C3 110.01(17) . . ? C111 C1 P1 109.55(14) . . ? C3 C1 P1 117.38(17) . . ? C211 C2 C3 108.58(16) . . ? C211 C2 P2 111.89(15) . . ? C3 C2 P2 116.90(17) . . ? C2 C3 C1 121.94(17) . . ? C12 C11 C21 130.0(2) . . ? C12 C11 P1 109.45(16) . . ? C21 C11 P1 120.33(16) . . ? C11 C12 C121 125.0(2) . . ? C11 C12 C13 114.1(2) . . ? C121 C12 C13 120.9(2) . . ? C14 C13 C12 115.4(2) . . ? C14 C13 C131 125.5(2) . . ? C12 C13 C131 119.2(2) . . ? C13 C14 C141 126.7(2) . . ? C13 C14 P1 108.14(16) . . ? C141 C14 P1 125.16(17) . . ? C22 C21 C11 129.7(2) . . ? C22 C21 P2 109.60(16) . . ? C11 C21 P2 120.39(16) . . ? C21 C22 C221 124.9(2) . . ? C21 C22 C23 113.6(2) . . ? C221 C22 C23 121.6(2) . . ? C24 C23 C22 115.4(2) . . ? C24 C23 C223 124.9(2) . . ? C22 C23 C223 119.6(2) . . ? C23 C24 C241 127.3(2) . . ? C23 C24 P2 108.76(17) . . ? C241 C24 P2 123.96(18) . . ? Cl1 C100 Cl1 111.3(3) 2_556 . ? C112 C111 C116 119.0(2) . . ? C112 C111 C1 122.3(2) . . ? C116 C111 C1 118.7(2) . . ? C111 C112 C113 120.5(3) . . ? C114 C113 C112 120.3(3) . . ? C115 C114 C113 119.9(3) . . ? C114 C115 C116 119.9(3) . . ? C111 C116 C115 120.4(3) . . ? C142 C141 C146 118.1(2) . . ? C142 C141 C14 121.7(2) . . ? C146 C141 C14 120.1(2) . . ? C141 C142 C143 121.3(3) . . ? C144 C143 C142 120.0(3) . . ? C143 C144 C145 120.0(2) . . ? C144 C145 C146 119.9(3) . . ? C141 C146 C145 120.7(3) . . ? Cl2A C200 C200 79.4(7) . 2_557 ? Cl2A C200 Cl2B 21.3(3) . . ? C200 C200 Cl2B 70.5(7) 2_557 . ? Cl2A C200 Cl2A 118.2(7) . 2_557 ? C200 C200 Cl2A 44.0(6) 2_557 2_557 ? Cl2B C200 Cl2A 114.1(5) . 2_557 ? Cl2A C200 Cl2B 136.1(7) . 2_557 ? C200 C200 Cl2B 57.2(6) 2_557 2_557 ? Cl2B C200 Cl2B 126.4(5) . 2_557 ? Cl2A C200 Cl2B 20.3(2) 2_557 2_557 ? C216 C211 C212 119.2(2) . . ? C216 C211 C2 119.3(2) . . ? C212 C211 C2 121.5(2) . . ? C211 C212 C213 120.5(3) . . ? C214 C213 C212 119.9(3) . . ? C215 C214 C213 120.0(3) . . ? C214 C215 C216 120.4(3) . . ? C211 C216 C215 120.0(3) . . ? C246 C241 C242 119.2(2) . . ? C246 C241 C24 120.5(3) . . ? C242 C241 C24 120.3(3) . . ? C241 C242 C243 119.5(3) . . ? C244 C243 C242 120.5(3) . . ? C245 C244 C243 120.1(3) . . ? C244 C245 C246 120.8(3) . . ? C241 C246 C245 119.9(3) . . ? Cl2B Cl2A C200 112.2(12) . . ? Cl2B Cl2A C200 81.6(10) . 2_557 ? C200 Cl2A C200 56.6(6) . 2_557 ? Cl2A Cl2B C200 46.5(10) . . ? Cl2A Cl2B C200 78.1(10) . 2_557 ? C200 Cl2B C200 52.3(5) . 2_557 ? C11 P1 C14 92.91(10) . . ? C11 P1 C1 104.02(10) . . ? C14 P1 C1 104.93(10) . . ? C11 P1 S1 113.86(8) . . ? C14 P1 S1 119.30(8) . . ? C1 P1 S1 118.09(8) . . ? C21 P2 C24 92.64(11) . . ? C21 P2 C2 103.44(10) . . ? C24 P2 C2 105.78(11) . . ? C21 P2 S2 114.95(9) . . ? C24 P2 S2 118.42(9) . . ? C2 P2 S2 117.91(8) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.432 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.050 #====END