# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Remi Chauvin' _publ_contact_author_email CHAUVIN@LCC-TOULOUSE.FR _publ_section_title ; Vicinal diphosphoniums: electrostatic repulsion under covalent constraint ; loop_ _publ_author_name 'Remi Chauvin' 'Mohammed Abdalilah' 'Gerald Bernardinelli' 'Yves Canac' 'Bruno Donnadieu' ; C.Duhayon ; 'Jerome Lacour' 'Benoit Laleu' 'C Lepetit' 'Germinal Magro' 'Marian Mikolajczyk' 'Remigiuz Zurawinski' # Attachment 'CIF_compound_2.cif' data_2[OTf]~2~ _database_code_depnum_ccdc_archive 'CCDC 710847' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H30 P2, 2(C F3 O3 S), 2(C0.80 H1.20 O0.40), H2 O' _chemical_formula_sum 'C35.6 H34.4 F6 O7.8 P2 S2' _chemical_formula_weight 827.12 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 P2/c _symmetry_space_group_name_Hall '-P 2yc ' 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 10.799(2) _cell_length_b 12.013(2) _cell_length_c 15.743(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.25(3) _cell_angle_gamma 90.00 _cell_volume 2026.0(6) _cell_formula_units_Z 2 _cell_measurement_temperature 295 _cell_measurement_reflns_used 7904 _cell_measurement_theta_min 2.1 _cell_measurement_theta_max 25.95 _exptl_crystal_description 'prism frag' _exptl_crystal_colour white _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 849 _exptl_absorpt_coefficient_mu 0.284 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.8998 _exptl_absorpt_correction_T_max 0.9722 _exptl_absorpt_process_details Difabs _exptl_special_details ; Data were collected at low temperature ( T = 295K ) on a STOE one circle Imaging Plate detector System CCD. A crystal decay was monitored and no fluctuations of the intensity were observed during data collection. Final unit cell parameters were obtained by the least-squares refinement of set well measured reflections. ; _diffrn_ambient_temperature 295 _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 'IPDS STOE' _diffrn_measurement_method 'phi scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11409 _diffrn_reflns_av_R_equivalents 0.0789 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 23.25 _reflns_number_total 2869 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE,s Area Detector Software Version 2003 ' _computing_cell_refinement 'STOE,s Area Detector Software Version 2003 ' _computing_data_reduction 'STOE,s Area Detector Software Version 2003 ' _computing_structure_solution SIR92 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3 for Windows' _computing_publication_material CIFTAB _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. Statistic disorders were found on the triflate anion: CF~3~SO~3~ and on a acetone molecule: CH~4~O. Some restraints were applied on interatomics bonds and angles and on ADP's parameters as well in order to get a chemically reasonable model. Occupancy factors were refined to be equal to the ratio: 55/45 % for the triflate anion and 40 % for the CH~4~O molecule. The structure was solved by using direct methods with the aid of SIR92 and refined by least-squares procedures on F^2^ using SHELXL-97. All hydrogens atoms were located on a difference Fourier maps, but were introduced in calculation in idealized positions with an isotropic thermal parameter fixed respectively at 20% higher than those of the C atoms to which they were connected. All non hydrogen atoms were anisotropically refined. A weighting scheme was used in the last refinement cycles, where weights are calculated from the following expression: w = [weight][1-((F)/6(F)]^2^. Models reached convergence with : Rw=[w(Fo-Fc)^2^/(Fo)^2^]^1/2^ and Rw=[w(Fo-Fc)^2^/(Fo)^2^]^1/2^, the criterion for a satisfactory complete analysis was the ratios of rms shift to standard deviation being less than 0.1 and no significant features in final difference maps. Calculations were performed by using WinGX programs, and drawings of molecules were realized with ORTEP3, atomic scattering factors were taken from International tables for X-Ray Crystallography. ; _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^)+(0.1073P)^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_number_reflns 2869 _refine_ls_number_parameters 315 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0979 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1652 _refine_ls_wR_factor_gt 0.1394 _refine_ls_goodness_of_fit_ref 0.933 _refine_ls_restrained_S_all 0.925 _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 P1 P 0.38020(9) 0.14066(9) 0.82441(7) 0.0576(4) Uani 1 1 d . . . C1 C 0.4876(4) 0.0389(4) 0.8712(3) 0.0669(11) Uani 1 1 d . . . H1A H 0.4449 -0.0125 0.9041 0.100 Uiso 1 1 calc R . . H1B H 0.5533 0.0749 0.9080 0.100 Uiso 1 1 calc R . . H1C H 0.5225 -0.0006 0.8268 0.100 Uiso 1 1 calc R . . C2 C 0.4543(3) 0.2592(3) 0.7794(3) 0.0570(10) Uani 1 1 d . . . C3 C 0.4134(4) 0.3618(3) 0.8055(3) 0.0737(12) Uani 1 1 d . . . H3 H 0.3539 0.3632 0.8433 0.088 Uiso 1 1 calc R . . C4 C 0.4569(5) 0.4618(4) 0.7778(3) 0.0857(14) Uani 1 1 d . . . H4 H 0.4272 0.5287 0.7972 0.103 Uiso 1 1 calc R . . C5 C 0.2977(4) 0.1914(3) 0.9086(3) 0.0635(11) Uani 1 1 d . . . C6 C 0.3613(5) 0.2080(5) 0.9901(3) 0.0864(14) Uani 1 1 d . . . H6 H 0.4455 0.1903 1.0022 0.104 Uiso 1 1 calc R . . C7 C 0.2958(7) 0.2516(5) 1.0529(4) 0.1085(19) Uani 1 1 d . . . H7 H 0.3360 0.2629 1.1080 0.130 Uiso 1 1 calc R . . C8 C 0.1721(7) 0.2779(5) 1.0339(5) 0.1067(19) Uani 1 1 d . . . H8 H 0.1293 0.3072 1.0765 0.128 Uiso 1 1 calc R . . C9 C 0.1109(5) 0.2620(5) 0.9547(5) 0.0972(17) Uani 1 1 d . . . H9 H 0.0269 0.2807 0.9432 0.117 Uiso 1 1 calc R . . C10 C 0.1719(4) 0.2187(4) 0.8914(3) 0.0789(13) Uani 1 1 d . . . H10 H 0.1294 0.2075 0.8370 0.095 Uiso 1 1 calc R . . C11 C 0.2705(3) 0.0791(3) 0.7441(3) 0.0584(10) Uani 1 1 d . . . C12 C 0.2303(4) 0.1325(4) 0.6679(3) 0.0745(12) Uani 1 1 d . . . H12 H 0.2614 0.2024 0.6566 0.089 Uiso 1 1 calc R . . C13 C 0.1427(5) 0.0807(5) 0.6080(4) 0.0915(15) Uani 1 1 d . . . H13 H 0.1167 0.1156 0.5561 0.110 Uiso 1 1 calc R . . C14 C 0.0948(5) -0.0214(5) 0.6253(4) 0.0899(15) Uani 1 1 d . . . H14 H 0.0347 -0.0544 0.5857 0.108 Uiso 1 1 calc R . . C15 C 0.1349(5) -0.0749(5) 0.7003(4) 0.0912(15) Uani 1 1 d . . . H15 H 0.1034 -0.1449 0.7112 0.109 Uiso 1 1 calc R . . C16 C 0.2219(4) -0.0250(4) 0.7596(3) 0.0772(13) Uani 1 1 d . . . H16 H 0.2485 -0.0613 0.8108 0.093 Uiso 1 1 calc R . . S1A S 0.2629(7) 0.7351(7) 0.9104(6) 0.070(3) Uani 0.55 1 d PD A 1 O1A O 0.3331(14) 0.8204(10) 0.9584(10) 0.080(3) Uani 0.55 1 d PD A 1 O2A O 0.3048(18) 0.708(2) 0.8301(10) 0.100(5) Uani 0.55 1 d PD A 1 O3A O 0.1306(7) 0.7459(15) 0.9079(13) 0.101(5) Uani 0.55 1 d PD A 1 S1B S 0.2582(11) 0.7287(8) 0.9150(7) 0.081(5) Uani 0.45 1 d PD A 2 O1B O 0.316(2) 0.8106(16) 0.9732(15) 0.132(10) Uani 0.45 1 d PD A 2 O2B O 0.330(2) 0.698(3) 0.8483(13) 0.119(8) Uani 0.45 1 d PD A 2 O3B O 0.1288(13) 0.748(2) 0.8870(17) 0.133(10) Uani 0.45 1 d PD A 2 C17 C 0.2803(4) 0.6083(4) 0.9750(3) 0.0992(17) Uani 1 1 d D . . F1A F 0.2495(18) 0.6225(18) 1.0514(8) 0.167(8) Uani 0.55 1 d PD A 1 F2A F 0.3955(8) 0.5742(15) 0.9842(13) 0.159(8) Uani 0.55 1 d PD A 1 F3A F 0.2140(15) 0.5255(11) 0.9409(11) 0.134(7) Uani 0.55 1 d PD A 1 F1B F 0.212(3) 0.611(2) 1.0374(12) 0.203(12) Uani 0.45 1 d PD A 2 F2B F 0.3954(9) 0.597(2) 1.0090(19) 0.210(15) Uani 0.45 1 d PD A 2 F3B F 0.250(2) 0.5180(14) 0.9318(16) 0.132(8) Uani 0.45 1 d PD A 2 O100 O 0.0000 0.6401(8) 0.2500 0.246(8) Uani 0.80 2 d SP . . C101 C 0.0000 0.5434(8) 0.2500 0.130(5) Uani 0.80 2 d SP . . C102 C 0.0823(10) 0.4758(11) 0.2024(7) 0.073(3) Uani 0.40 1 d P . . H10A H 0.1355 0.5240 0.1746 0.110 Uiso 0.40 1 calc PR . . H10B H 0.0324 0.4317 0.1602 0.110 Uiso 0.40 1 calc PR . . H10C H 0.1324 0.4277 0.2415 0.110 Uiso 0.40 1 calc PR . . O1W O 0.5000 0.8148(5) 0.7500 0.1188(18) Uani 1 2 d S . . 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 P1 0.0523(6) 0.0557(6) 0.0652(7) 0.0041(5) 0.0082(5) -0.0004(5) C1 0.065(2) 0.068(3) 0.068(3) 0.008(2) 0.005(2) 0.003(2) C2 0.053(2) 0.053(2) 0.066(2) 0.0019(18) 0.0089(18) 0.0003(17) C3 0.078(3) 0.061(3) 0.088(3) 0.002(2) 0.032(2) 0.005(2) C4 0.109(4) 0.051(2) 0.105(4) -0.003(2) 0.045(3) 0.003(2) C5 0.064(3) 0.062(2) 0.066(3) 0.002(2) 0.015(2) -0.004(2) C6 0.086(3) 0.101(4) 0.073(3) -0.002(3) 0.012(3) 0.009(3) C7 0.137(6) 0.118(5) 0.073(4) -0.006(3) 0.022(4) -0.003(4) C8 0.122(5) 0.103(4) 0.107(5) -0.003(4) 0.062(4) -0.003(4) C9 0.075(3) 0.097(4) 0.127(5) -0.011(4) 0.042(4) -0.009(3) C10 0.061(3) 0.084(3) 0.094(3) -0.006(3) 0.019(2) 0.000(2) C11 0.055(2) 0.057(2) 0.064(3) 0.003(2) 0.009(2) -0.0015(18) C12 0.066(3) 0.072(3) 0.082(3) 0.011(3) -0.002(2) -0.004(2) C13 0.078(3) 0.103(4) 0.090(4) 0.006(3) -0.007(3) 0.006(3) C14 0.073(3) 0.096(4) 0.096(4) -0.015(3) -0.009(3) -0.005(3) C15 0.092(4) 0.080(3) 0.100(4) -0.006(3) 0.001(3) -0.020(3) C16 0.082(3) 0.072(3) 0.075(3) 0.007(2) 0.001(3) -0.012(2) S1A 0.056(4) 0.059(4) 0.096(6) 0.019(3) 0.010(3) 0.006(2) O1A 0.075(5) 0.066(5) 0.099(6) 0.007(5) 0.012(5) -0.015(5) O2A 0.134(9) 0.092(10) 0.078(6) 0.015(6) 0.027(6) 0.021(7) O3A 0.051(8) 0.117(12) 0.136(9) -0.018(8) 0.014(5) 0.017(6) S1B 0.094(8) 0.070(6) 0.084(6) -0.024(4) 0.031(4) -0.017(4) O1B 0.133(13) 0.109(12) 0.158(17) -0.061(13) 0.039(10) -0.058(9) O2B 0.172(17) 0.089(9) 0.116(13) 0.027(10) 0.097(16) 0.033(11) O3B 0.091(14) 0.105(13) 0.19(2) 0.048(12) -0.033(11) -0.012(9) C17 0.124(5) 0.079(4) 0.096(5) 0.003(3) 0.018(4) 0.005(4) F1A 0.31(2) 0.116(9) 0.086(7) 0.004(6) 0.060(9) -0.011(13) F2A 0.178(16) 0.140(10) 0.152(9) 0.022(7) -0.003(8) 0.099(12) F3A 0.179(12) 0.079(8) 0.143(11) 0.009(6) 0.022(10) -0.029(7) F1B 0.29(2) 0.17(2) 0.183(19) 0.055(16) 0.166(18) 0.047(15) F2B 0.19(2) 0.176(18) 0.24(3) 0.088(17) -0.076(19) -0.017(14) F3B 0.182(14) 0.058(6) 0.176(15) -0.006(7) 0.098(12) -0.005(7) O100 0.48(2) 0.094(7) 0.124(7) 0.000 -0.116(11) 0.000 C101 0.222(14) 0.057(5) 0.084(7) 0.000 -0.089(9) 0.000 C102 0.064(6) 0.103(9) 0.055(6) -0.013(6) 0.016(5) -0.011(6) O1W 0.127(4) 0.099(4) 0.136(5) 0.000 0.041(4) 0.000 _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 P1 C1 1.780(4) . ? P1 C11 1.781(4) . ? P1 C5 1.795(4) . ? P1 C2 1.820(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.390(6) . ? C2 C2 1.435(8) 2_656 ? C3 C4 1.380(6) . ? C3 H3 0.9300 . ? C4 C4 1.357(9) 2_656 ? C4 H4 0.9300 . ? C5 C10 1.390(6) . ? C5 C6 1.390(6) . ? C6 C7 1.389(8) . ? C6 H6 0.9300 . ? C7 C8 1.368(9) . ? C7 H7 0.9300 . ? C8 C9 1.349(8) . ? C8 H8 0.9300 . ? C9 C10 1.365(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C12 1.381(6) . ? C11 C16 1.389(6) . ? C12 C13 1.395(7) . ? C12 H12 0.9300 . ? C13 C14 1.371(8) . ? C13 H13 0.9300 . ? C14 C15 1.366(7) . ? C14 H14 0.9300 . ? C15 C16 1.376(6) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? S1A O3A 1.430(4) . ? S1A O2A 1.432(5) . ? S1A O1A 1.432(4) . ? S1A C17 1.828(10) . ? S1B O3B 1.430(5) . ? S1B O1B 1.433(5) . ? S1B O2B 1.433(5) . ? S1B C17 1.727(12) . ? C17 F2B 1.298(6) . ? C17 F3B 1.299(5) . ? C17 F1B 1.300(5) . ? C17 F1A 1.300(5) . ? C17 F2A 1.300(5) . ? C17 F3A 1.301(5) . ? O100 C101 1.162(12) . ? C101 C102 1.476(12) . ? C101 C102 1.476(12) 2 ? C102 H10A 0.9600 . ? C102 H10B 0.9600 . ? C102 H10C 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 C1 P1 C11 110.4(2) . . ? C1 P1 C5 106.6(2) . . ? C11 P1 C5 108.55(19) . . ? C1 P1 C2 113.77(19) . . ? C11 P1 C2 109.51(19) . . ? C5 P1 C2 107.81(19) . . ? P1 C1 H1A 109.5 . . ? P1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? P1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C2 117.4(2) . 2_656 ? C3 C2 P1 114.0(3) . . ? C2 C2 P1 128.54(13) 2_656 . ? C4 C3 C2 123.1(4) . . ? C4 C3 H3 118.5 . . ? C2 C3 H3 118.5 . . ? C4 C4 C3 119.5(3) 2_656 . ? C4 C4 H4 120.3 2_656 . ? C3 C4 H4 120.3 . . ? C10 C5 C6 120.2(4) . . ? C10 C5 P1 120.0(4) . . ? C6 C5 P1 119.7(3) . . ? C7 C6 C5 118.3(5) . . ? C7 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C8 C7 C6 120.2(6) . . ? C8 C7 H7 119.9 . . ? C6 C7 H7 119.9 . . ? C9 C8 C7 121.3(6) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 120.2(6) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 119.8(5) . . ? C9 C10 H10 120.1 . . ? C5 C10 H10 120.1 . . ? C12 C11 C16 119.1(4) . . ? C12 C11 P1 122.1(3) . . ? C16 C11 P1 118.8(3) . . ? C11 C12 C13 119.5(4) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.4(5) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 120.4(5) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.7(5) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C15 C16 C11 120.9(4) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? O3A S1A O2A 115.0(5) . . ? O3A S1A O1A 114.2(4) . . ? O2A S1A O1A 115.0(5) . . ? O3A S1A C17 97.1(9) . . ? O2A S1A C17 106.3(11) . . ? O1A S1A C17 107.0(7) . . ? O3B S1B O1B 114.5(6) . . ? O3B S1B O2B 114.6(6) . . ? O1B S1B O2B 114.6(6) . . ? O3B S1B C17 111.5(12) . . ? O1B S1B C17 101.9(11) . . ? O2B S1B C17 97.6(13) . . ? F2B C17 F3B 106.7(6) . . ? F2B C17 F1B 107.1(6) . . ? F3B C17 F1B 107.0(6) . . ? F2B C17 F1A 89(2) . . ? F3B C17 F1A 121.2(19) . . ? F3B C17 F2A 88.1(16) . . ? F1B C17 F2A 123(2) . . ? F1A C17 F2A 106.9(6) . . ? F2B C17 F3A 122.4(19) . . ? F1B C17 F3A 89.9(17) . . ? F1A C17 F3A 106.8(6) . . ? F2A C17 F3A 105.9(6) . . ? F2B C17 S1B 112.0(14) . . ? F3B C17 S1B 113.9(13) . . ? F1B C17 S1B 109.8(14) . . ? F1A C17 S1B 111.3(11) . . ? F2A C17 S1B 112.9(11) . . ? F3A C17 S1B 112.6(11) . . ? F2B C17 S1A 110.2(14) . . ? F3B C17 S1A 113.8(13) . . ? F1B C17 S1A 111.7(14) . . ? F1A C17 S1A 112.7(11) . . ? F2A C17 S1A 110.8(10) . . ? F3A C17 S1A 113.3(10) . . ? O100 C101 C102 123.4(6) . . ? O100 C101 C102 123.4(6) . 2 ? C102 C101 C102 113.2(11) . 2 ? C101 C102 H10A 109.5 . . ? C101 C102 H10B 109.5 . . ? H10A C102 H10B 109.5 . . ? C101 C102 H10C 109.5 . . ? H10A C102 H10C 109.5 . . ? H10B C102 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.25 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.413 _refine_diff_density_min -0.250 _refine_diff_density_rms 0.056 data_compound3 _database_code_depnum_ccdc_archive 'CCDC 710848' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C31 H26 P2, 2 (I)' _chemical_formula_sum 'C31 H26 I2 P2' _chemical_formula_weight 714.26 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 8.8695(4) _cell_length_b 18.8576(8) _cell_length_c 34.5533(14) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 5779.3(4) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9949 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 26.89 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'hexagonal platelet' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.642 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2784 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 2.305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.7392 _exptl_absorpt_correction_T_max 0.8955 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _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 Kappa APEX II' _diffrn_measurement_method \w-\f _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_unetI/netI 0.0359 _diffrn_reflns_number 82939 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -50 _diffrn_reflns_limit_l_max 50 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 30.99 _diffrn_reflns_theta_full 30.99 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 9191 _reflns_number_gt 6529 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0239P)^2^+5.3418P] 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_number_reflns 9191 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.0699 _refine_ls_wR_factor_gt 0.0618 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.936 _refine_diff_density_min -0.838 _refine_diff_density_rms 0.099 #----------------------------------------------------------------------------# # 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' I I -0.4742 1.8119 '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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4176(3) 0.59024(12) 0.12808(7) 0.0206(5) Uani 1 1 d . . . H1A H 0.4224 0.6342 0.1437 0.025 Uiso 1 1 calc R . . H1B H 0.5212 0.5723 0.1239 0.025 Uiso 1 1 calc R . . C2 C 0.2394(3) 0.47885(12) 0.10847(7) 0.0234(5) Uani 1 1 d . . . C3 C 0.1725(3) 0.41243(13) 0.10810(9) 0.0341(6) Uani 1 1 d . . . H3 H 0.1609 0.3864 0.1314 0.041 Uiso 1 1 calc R . . C4 C 0.1231(4) 0.38479(14) 0.07358(10) 0.0407(8) Uani 1 1 d . . . H4 H 0.0771 0.3393 0.0732 0.049 Uiso 1 1 calc R . . C5 C 0.1393(4) 0.42196(15) 0.03950(10) 0.0405(7) Uani 1 1 d . . . H5 H 0.1047 0.4017 0.0159 0.049 Uiso 1 1 calc R . . C6 C 0.2057(3) 0.48875(14) 0.03923(8) 0.0314(6) Uani 1 1 d . . . H6 H 0.2165 0.5144 0.0157 0.038 Uiso 1 1 calc R . . C7 C 0.2558(3) 0.51709(13) 0.07393(7) 0.0228(5) Uani 1 1 d . . . C8 C 0.4057(3) 0.46752(13) 0.18261(7) 0.0249(5) Uani 1 1 d . . . C9 C 0.5322(3) 0.43351(14) 0.16803(8) 0.0299(6) Uani 1 1 d . . . H9 H 0.5655 0.4425 0.1424 0.036 Uiso 1 1 calc R . . C10 C 0.6091(3) 0.38629(14) 0.19142(9) 0.0350(7) Uani 1 1 d . . . H10 H 0.6956 0.3625 0.1817 0.042 Uiso 1 1 calc R . . C11 C 0.5611(3) 0.37362(15) 0.22870(9) 0.0398(7) Uani 1 1 d . . . H11 H 0.6133 0.3402 0.2443 0.048 Uiso 1 1 calc R . . C12 C 0.4379(4) 0.40895(18) 0.24347(10) 0.0508(9) Uani 1 1 d . . . H12 H 0.4073 0.401 0.2695 0.061 Uiso 1 1 calc R . . C13 C 0.3585(4) 0.45629(18) 0.22029(9) 0.0430(8) Uani 1 1 d . . . H13 H 0.273 0.4806 0.2302 0.052 Uiso 1 1 calc R . . C14 C 0.1451(3) 0.56481(14) 0.17531(7) 0.0267(5) Uani 1 1 d . . . C15 C 0.1709(4) 0.62299(16) 0.19892(9) 0.0423(8) Uani 1 1 d . . . H15 H 0.2708 0.6393 0.2033 0.051 Uiso 1 1 calc R . . C16 C 0.0503(5) 0.6570(2) 0.21599(11) 0.0571(10) Uani 1 1 d . . . H16 H 0.0672 0.6969 0.2322 0.068 Uiso 1 1 calc R . . C17 C -0.0933(5) 0.6336(2) 0.20972(11) 0.0642(12) Uani 1 1 d . . . H17 H -0.176 0.6575 0.2213 0.077 Uiso 1 1 calc R . . C18 C -0.1183(4) 0.5753(3) 0.18661(12) 0.0746(13) Uani 1 1 d . . . H18 H -0.2183 0.5589 0.1827 0.09 Uiso 1 1 calc R . . C19 C 0.0001(4) 0.5407(2) 0.16915(10) 0.0526(9) Uani 1 1 d . . . H19 H -0.0177 0.5007 0.1531 0.063 Uiso 1 1 calc R . . C20 C 0.4445(3) 0.64686(12) 0.04833(7) 0.0226(5) Uani 1 1 d . . . C21 C 0.4436(3) 0.62776(15) 0.00971(8) 0.0346(7) Uani 1 1 d . . . H21 H 0.385 0.5886 0.0012 0.042 Uiso 1 1 calc R . . C22 C 0.5288(4) 0.66625(17) -0.01643(9) 0.0442(8) Uani 1 1 d . . . H22 H 0.5289 0.6535 -0.043 0.053 Uiso 1 1 calc R . . C23 C 0.6134(4) 0.72290(15) -0.00398(9) 0.0416(8) Uani 1 1 d . . . H23 H 0.6716 0.749 -0.0221 0.05 Uiso 1 1 calc R . . C24 C 0.6149(4) 0.74217(15) 0.03425(9) 0.0373(7) Uani 1 1 d . . . H24 H 0.6739 0.7814 0.0425 0.045 Uiso 1 1 calc R . . C25 C 0.5301(3) 0.70422(13) 0.06081(8) 0.0282(6) Uani 1 1 d . . . H25 H 0.5305 0.7173 0.0874 0.034 Uiso 1 1 calc R . . C26 C 0.1608(3) 0.65952(12) 0.09150(7) 0.0219(5) Uani 1 1 d . . . C27 C 0.1790(3) 0.72589(14) 0.10879(8) 0.0327(6) Uani 1 1 d . . . H27 H 0.2772 0.7436 0.1141 0.039 Uiso 1 1 calc R . . C28 C 0.0542(3) 0.76542(17) 0.11804(9) 0.0403(7) Uani 1 1 d . . . H28 H 0.0666 0.8108 0.1296 0.048 Uiso 1 1 calc R . . C29 C -0.0876(4) 0.74048(17) 0.11086(11) 0.0482(9) Uani 1 1 d . . . H29 H -0.1733 0.7679 0.1177 0.058 Uiso 1 1 calc R . . C30 C -0.1052(4) 0.67528(17) 0.09363(13) 0.0607(11) Uani 1 1 d . . . H30 H -0.2037 0.658 0.0884 0.073 Uiso 1 1 calc R . . C31 C 0.0180(3) 0.63474(15) 0.08392(10) 0.0427(8) Uani 1 1 d . . . H31 H 0.0045 0.5898 0.072 0.051 Uiso 1 1 calc R . . P1 P 0.30094(7) 0.52408(3) 0.151257(19) 0.02148(13) Uani 1 1 d . . . P2 P 0.32291(7) 0.60558(3) 0.082727(18) 0.01906(12) Uani 1 1 d . . . I1 I 0.97748(2) 0.263125(9) 0.176398(5) 0.03303(5) Uani 1 1 d . . . I2 I 0.72193(2) 0.484947(11) 0.072471(6) 0.03639(5) 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 0.0207(12) 0.0213(11) 0.0199(12) -0.0003(9) -0.0004(10) -0.0004(9) C2 0.0245(13) 0.0209(11) 0.0247(13) 0.0009(10) -0.0003(10) 0.0003(9) C3 0.0365(16) 0.0241(12) 0.0419(18) 0.0069(12) -0.0043(13) -0.0048(11) C4 0.0450(18) 0.0210(12) 0.056(2) -0.0031(13) -0.0143(16) -0.0077(12) C5 0.0453(19) 0.0316(14) 0.0447(19) -0.0144(13) -0.0102(15) -0.0031(13) C6 0.0360(16) 0.0321(13) 0.0260(14) -0.0036(11) -0.0019(12) -0.0045(12) C7 0.0245(13) 0.0227(11) 0.0211(12) -0.0011(10) -0.0002(10) -0.0006(10) C8 0.0229(13) 0.0250(11) 0.0267(14) 0.0077(10) -0.0005(10) -0.0012(9) C9 0.0333(15) 0.0320(13) 0.0244(14) 0.0017(10) -0.0004(12) 0.0047(11) C10 0.0364(17) 0.0329(14) 0.0358(17) -0.0010(12) -0.0049(13) 0.0108(12) C11 0.0355(17) 0.0368(15) 0.0470(19) 0.0183(14) -0.0119(14) 0.0013(13) C12 0.045(2) 0.069(2) 0.0384(19) 0.0292(17) 0.0051(16) 0.0091(17) C13 0.0347(17) 0.061(2) 0.0338(17) 0.0216(15) 0.0099(14) 0.0107(15) C14 0.0272(14) 0.0333(13) 0.0198(13) 0.0079(11) 0.0048(11) 0.0070(10) C15 0.0403(18) 0.0458(17) 0.0408(19) -0.0073(14) 0.0112(15) 0.0032(14) C16 0.068(3) 0.057(2) 0.047(2) -0.0077(17) 0.0193(19) 0.0199(19) C17 0.054(2) 0.100(3) 0.039(2) 0.006(2) 0.0158(18) 0.040(2) C18 0.0274(19) 0.136(4) 0.060(3) -0.016(3) 0.0058(18) 0.011(2) C19 0.0303(19) 0.077(3) 0.051(2) -0.0136(18) 0.0049(15) 0.0000(16) C20 0.0229(13) 0.0232(11) 0.0218(13) 0.0051(9) 0.0041(10) 0.0030(9) C21 0.0407(17) 0.0389(15) 0.0244(15) -0.0008(12) 0.0043(13) -0.0078(13) C22 0.054(2) 0.0534(19) 0.0250(16) 0.0045(14) 0.0098(15) -0.0021(16) C23 0.0437(18) 0.0401(16) 0.0410(18) 0.0158(14) 0.0162(15) -0.0006(14) C24 0.0402(18) 0.0303(13) 0.0415(18) 0.0047(13) 0.0088(14) -0.0072(12) C25 0.0310(14) 0.0285(12) 0.0252(14) 0.0016(10) 0.0047(11) -0.0011(11) C26 0.0219(12) 0.0236(11) 0.0202(12) 0.0051(9) -0.0011(10) 0.0013(9) C27 0.0260(14) 0.0332(14) 0.0389(16) -0.0107(12) -0.0012(12) 0.0030(11) C28 0.0354(18) 0.0427(16) 0.0429(18) -0.0118(14) 0.0021(14) 0.0094(14) C29 0.0281(16) 0.0465(17) 0.070(3) 0.0076(17) 0.0084(16) 0.0144(14) C30 0.0228(17) 0.0398(17) 0.120(4) 0.003(2) -0.009(2) 0.0007(13) C31 0.0287(15) 0.0276(13) 0.072(2) 0.0014(14) -0.0124(15) 0.0001(12) P1 0.0226(3) 0.0220(3) 0.0198(3) 0.0041(2) 0.0012(3) 0.0005(2) P2 0.0217(3) 0.0179(3) 0.0176(3) 0.0012(2) -0.0001(2) -0.0014(2) I1 0.03657(10) 0.03178(8) 0.03073(10) -0.00771(8) 0.00471(8) 0.00662(7) I2 0.03585(10) 0.04554(11) 0.02778(10) -0.00725(8) 0.00380(8) -0.00345(9) #----------------------------------------------------------------------------# # 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 C1 P2 1.801(2) . ? C1 P1 1.808(2) . ? C1 H1A 0.99 . ? C1 H1B 0.99 . ? C2 C3 1.386(3) . ? C2 C7 1.402(3) . ? C2 P1 1.792(3) . ? C3 C4 1.373(4) . ? C3 H3 0.95 . ? C4 C5 1.378(4) . ? C4 H4 0.95 . ? C5 C6 1.391(4) . ? C5 H5 0.95 . ? C6 C7 1.386(4) . ? C6 H6 0.95 . ? C7 P2 1.798(2) . ? C8 C13 1.384(4) . ? C8 C9 1.388(4) . ? C8 P1 1.782(3) . ? C9 C10 1.383(4) . ? C9 H9 0.95 . ? C10 C11 1.378(4) . ? C10 H10 0.95 . ? C11 C12 1.377(4) . ? C11 H11 0.95 . ? C12 C13 1.391(4) . ? C12 H12 0.95 . ? C13 H13 0.95 . ? C14 C19 1.381(4) . ? C14 C15 1.386(4) . ? C14 P1 1.786(3) . ? C15 C16 1.380(4) . ? C15 H15 0.95 . ? C16 C17 1.365(6) . ? C16 H16 0.95 . ? C17 C18 1.376(6) . ? C17 H17 0.95 . ? C18 C19 1.376(5) . ? C18 H18 0.95 . ? C19 H19 0.95 . ? C20 C21 1.382(4) . ? C20 C25 1.390(4) . ? C20 P2 1.783(2) . ? C21 C22 1.384(4) . ? C21 H21 0.95 . ? C22 C23 1.375(4) . ? C22 H22 0.95 . ? C23 C24 1.370(4) . ? C23 H23 0.95 . ? C24 C25 1.386(4) . ? C24 H24 0.95 . ? C25 H25 0.95 . ? C26 C31 1.375(4) . ? C26 C27 1.396(3) . ? C26 P2 1.787(3) . ? C27 C28 1.372(4) . ? C27 H27 0.95 . ? C28 C29 1.366(5) . ? C28 H28 0.95 . ? C29 C30 1.375(5) . ? C29 H29 0.95 . ? C30 C31 1.375(4) . ? C30 H30 0.95 . ? C31 H31 0.95 . ? 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 P2 C1 P1 103.25(12) . . ? P2 C1 H1A 111.1 . . ? P1 C1 H1A 111.1 . . ? P2 C1 H1B 111.1 . . ? P1 C1 H1B 111.1 . . ? H1A C1 H1B 109.1 . . ? C3 C2 C7 120.1(2) . . ? C3 C2 P1 124.6(2) . . ? C7 C2 P1 115.20(18) . . ? C4 C3 C2 119.2(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 121.1(3) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 120.7(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 118.6(3) . . ? C7 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? C6 C7 C2 120.3(2) . . ? C6 C7 P2 127.6(2) . . ? C2 C7 P2 111.58(18) . . ? C13 C8 C9 121.0(2) . . ? C13 C8 P1 120.4(2) . . ? C9 C8 P1 118.5(2) . . ? C10 C9 C8 119.0(3) . . ? C10 C9 H9 120.5 . . ? C8 C9 H9 120.5 . . ? C11 C10 C9 120.4(3) . . ? C11 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? C12 C11 C10 120.5(3) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.9(3) . . ? C11 C12 H12 120 . . ? C13 C12 H12 120 . . ? C8 C13 C12 119.1(3) . . ? C8 C13 H13 120.4 . . ? C12 C13 H13 120.4 . . ? C19 C14 C15 120.3(3) . . ? C19 C14 P1 120.5(2) . . ? C15 C14 P1 119.1(2) . . ? C16 C15 C14 119.4(3) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C17 C16 C15 120.3(4) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 120.1(3) . . ? C16 C17 H17 120 . . ? C18 C17 H17 120 . . ? C17 C18 C19 120.7(4) . . ? C17 C18 H18 119.7 . . ? C19 C18 H18 119.7 . . ? C18 C19 C14 119.1(4) . . ? C18 C19 H19 120.4 . . ? C14 C19 H19 120.4 . . ? C21 C20 C25 120.4(2) . . ? C21 C20 P2 121.8(2) . . ? C25 C20 P2 117.58(19) . . ? C20 C21 C22 119.4(3) . . ? C20 C21 H21 120.3 . . ? C22 C21 H21 120.3 . . ? C23 C22 C21 120.1(3) . . ? C23 C22 H22 120 . . ? C21 C22 H22 120 . . ? C24 C23 C22 120.9(3) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.8(3) . . ? C23 C24 H24 120.1 . . ? C25 C24 H24 120.1 . . ? C24 C25 C20 119.5(3) . . ? C24 C25 H25 120.2 . . ? C20 C25 H25 120.2 . . ? C31 C26 C27 119.5(2) . . ? C31 C26 P2 121.0(2) . . ? C27 C26 P2 119.3(2) . . ? C28 C27 C26 119.5(3) . . ? C28 C27 H27 120.2 . . ? C26 C27 H27 120.2 . . ? C29 C28 C27 120.9(3) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 119.4(3) . . ? C28 C29 H29 120.3 . . ? C30 C29 H29 120.3 . . ? C31 C30 C29 120.8(3) . . ? C31 C30 H30 119.6 . . ? C29 C30 H30 119.6 . . ? C26 C31 C30 119.8(3) . . ? C26 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C8 P1 C14 112.20(12) . . ? C8 P1 C2 112.06(12) . . ? C14 P1 C2 110.65(12) . . ? C8 P1 C1 112.59(12) . . ? C14 P1 C1 110.62(12) . . ? C2 P1 C1 97.90(11) . . ? C20 P2 C26 110.55(11) . . ? C20 P2 C7 119.51(12) . . ? C26 P2 C7 106.89(12) . . ? C20 P2 C1 111.59(12) . . ? C26 P2 C1 108.61(12) . . ? C7 P2 C1 98.77(11) . . ? data_compound4 _database_code_depnum_ccdc_archive 'CCDC 710849' _audit_creation_date 07-06-04 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 9.5353(9) _cell_length_b 19.6190(13) _cell_length_c 19.8829(18) _cell_angle_alpha 90 _cell_angle_beta 99.024(11) _cell_angle_gamma 90 _cell_volume 3673.5(6) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C34 H28 F6 O6 P2 S2' _chemical_formula_moiety 'C32 H28 P2, 2(C F3 O3 S)' _chemical_compound_source ? _chemical_formula_weight 772.66 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 3 _cell_measurement_theta_max 25 _cell_measurement_temperature 180 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.30 _exptl_crystal_density_diffrn 1.397 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 0.305 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Stoe IPDS' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'IPDS (Stoe & Cie, 1996)' _computing_cell_refinement 'IPDS (Stoe & Cie, 1996)' _computing_data_reduction 'XRED (Stoe & Cie 1996)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 36701 _reflns_number_total 7171 _diffrn_reflns_av_R_equivalents 0.080 # Number of reflections with Friedels Law is 7171 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 7214 _diffrn_reflns_theta_min 2.074 _diffrn_reflns_theta_max 25.991 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.471 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 24 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.40 _refine_diff_density_max 0.57 _refine_ls_number_reflns 3884 _refine_ls_number_restraints 0 _refine_ls_number_parameters 451 #_refine_ls_R_factor_ref 0.0559 _refine_ls_wR_factor_ref 0.0640 _refine_ls_goodness_of_fit_ref 1.0900 #_reflns_number_all 7143 _refine_ls_R_factor_all 0.1119 _refine_ls_wR_factor_all 0.0917 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>0.8\s(I) _reflns_number_gt 3884 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_gt 0.0640 _refine_ls_shift/su_max 0.000236 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.10 0.561 0.569 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Stoe & Cie (1996). IPDS Software. Stoe & Cie (1996). XRED V1.08. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.4428(5) 0.1217(2) 0.3872(2) 0.0488 1.0000 Uani . . . . . . C2 C 0.5227(4) 0.1541(2) 0.3336(2) 0.0426 1.0000 Uani . . . . . . C3 C 0.2531(4) 0.06176(19) 0.2718(2) 0.0334 1.0000 Uani . . . . . . C4 C 0.1655(4) 0.0074(2) 0.2481(2) 0.0413 1.0000 Uani . . . . . . C5 C 0.1461(5) -0.0117(2) 0.1810(2) 0.0462 1.0000 Uani . . . . . . C6 C 0.2162(5) 0.0219(2) 0.1353(2) 0.0469 1.0000 Uani . . . . . . C7 C 0.3044(5) 0.0762(2) 0.1569(2) 0.0445 1.0000 Uani . . . . . . C8 C 0.3240(4) 0.09728(18) 0.2245(2) 0.0339 1.0000 Uani . . . . . . C9 C 0.2442(5) 0.0109(2) 0.4069(2) 0.0427 1.0000 Uani . . . . . . C10 C 0.3536(5) -0.0369(2) 0.4218(2) 0.0538 1.0000 Uani . . . . . . C11 C 0.3271(6) -0.0979(3) 0.4528(3) 0.0658 1.0000 Uani . . . . . . C12 C 0.1959(7) -0.1119(3) 0.4691(3) 0.0719 1.0000 Uani . . . . . . C13 C 0.0879(7) -0.0653(3) 0.4539(3) 0.0728 1.0000 Uani . . . . . . C14 C 0.1113(5) -0.0035(2) 0.4235(3) 0.0577 1.0000 Uani . . . . . . C15 C 0.1369(4) 0.1471(2) 0.3689(2) 0.0430 1.0000 Uani . . . . . . C16 C 0.0289(4) 0.1622(2) 0.3166(3) 0.0482 1.0000 Uani . . . . . . C17 C -0.0722(5) 0.2112(2) 0.3250(3) 0.0608 1.0000 Uani . . . . . . C18 C -0.0641(6) 0.2443(3) 0.3865(4) 0.0716 1.0000 Uani . . . . . . C19 C 0.0418(7) 0.2297(3) 0.4397(3) 0.0807 1.0000 Uani . . . . . . C20 C 0.1428(6) 0.1809(3) 0.4308(3) 0.0654 1.0000 Uani . . . . . . C21 C 0.3079(4) 0.24090(19) 0.2501(2) 0.0378 1.0000 Uani . . . . . . C22 C 0.2122(4) 0.2532(2) 0.1907(2) 0.0467 1.0000 Uani . . . . . . C23 C 0.1169(5) 0.3063(3) 0.1893(3) 0.0554 1.0000 Uani . . . . . . C24 C 0.1157(5) 0.3463(2) 0.2457(3) 0.0562 1.0000 Uani . . . . . . C25 C 0.2080(4) 0.3336(2) 0.3044(3) 0.0514 1.0000 Uani . . . . . . C26 C 0.3065(4) 0.28171(19) 0.3071(2) 0.0430 1.0000 Uani . . . . . . C27 C 0.5544(4) 0.1862(2) 0.1963(3) 0.0481 1.0000 Uani . . . . . . C28 C 0.6471(5) 0.1334(2) 0.1851(3) 0.0614 1.0000 Uani . . . . . . C29 C 0.7527(6) 0.1463(3) 0.1464(3) 0.0750 1.0000 Uani . . . . . . C30 C 0.7679(6) 0.2097(3) 0.1196(3) 0.0720 1.0000 Uani . . . . . . C31 C 0.6768(6) 0.2622(3) 0.1301(3) 0.0693 1.0000 Uani . . . . . . C32 C 0.5694(5) 0.2502(2) 0.1687(3) 0.0576 1.0000 Uani . . . . . . C33 C 0.7822(5) -0.0660(3) 0.2618(4) 0.0891 1.0000 Uani . . . . . . C34 C 0.0073(5) 0.1246(2) -0.0086(2) 0.0481 1.0000 Uani . . . . . . P1 P 0.26922(11) 0.08542(5) 0.35913(6) 0.0388 1.0000 Uani . . . . . . P2 P 0.42716(10) 0.17117(5) 0.25098(6) 0.0390 1.0000 Uani . . . . . . S1 S 0.70615(14) -0.02225(6) 0.32691(10) 0.0808 1.0000 Uani . . . . . . S2 S 0.10562(11) 0.20170(5) -0.01486(6) 0.0454 1.0000 Uani . . . . . . O1 O 0.5673(3) -0.00362(17) 0.2934(2) 0.0826 1.0000 Uani . . . . . . O2 O 0.7065(5) -0.0729(2) 0.3780(3) 0.1064 1.0000 Uani . . . . . . O3 O 0.7987(4) 0.03485(19) 0.3425(3) 0.1209 1.0000 Uani . . . . . . O4 O 0.2374(3) 0.18989(18) 0.02870(17) 0.0618 1.0000 Uani . . . . . . O5 O 0.1146(4) 0.2048(2) -0.08645(17) 0.0701 1.0000 Uani . . . . . . O6 O 0.0142(4) 0.25225(16) 0.0076(2) 0.0743 1.0000 Uani . . . . . . F1 F 0.9132(3) -0.08982(15) 0.2852(2) 0.1041 1.0000 Uani . . . . . . F2 F 0.7078(4) -0.1195(2) 0.2371(3) 0.1174 1.0000 Uani . . . . . . F3 F 0.7979(4) -0.0241(2) 0.2106(3) 0.1367 1.0000 Uani . . . . . . F4 F -0.0098(3) 0.11067(14) 0.05524(14) 0.0642 1.0000 Uani . . . . . . F5 F 0.0694(4) 0.06960(14) -0.03048(16) 0.0765 1.0000 Uani . . . . . . F6 F -0.1233(3) 0.12788(16) -0.04444(16) 0.0755 1.0000 Uani . . . . . . H11 H 0.4313 0.1568 0.4203 0.0602 1.0000 Uiso R . . . . . H12 H 0.5024 0.0854 0.4100 0.0601 1.0000 Uiso R . . . . . H21 H 0.5638 0.1971 0.3521 0.0512 1.0000 Uiso R . . . . . H22 H 0.5974 0.1226 0.3262 0.0513 1.0000 Uiso R . . . . . H41 H 0.1185 -0.0163 0.2791 0.0503 1.0000 Uiso R . . . . . H51 H 0.0856 -0.0480 0.1660 0.0563 1.0000 Uiso R . . . . . H61 H 0.2027 0.0082 0.0897 0.0592 1.0000 Uiso R . . . . . H71 H 0.3510 0.0998 0.1263 0.0562 1.0000 Uiso R . . . . . H101 H 0.4432 -0.0264 0.4113 0.0692 1.0000 Uiso R . . . . . H111 H 0.4010 -0.1299 0.4624 0.0792 1.0000 Uiso R . . . . . H131 H -0.0025 -0.0745 0.4651 0.0971 1.0000 Uiso R . . . . . H141 H 0.0378 0.0281 0.4126 0.0711 1.0000 Uiso R . . . . . H161 H 0.0227 0.1398 0.2749 0.0603 1.0000 Uiso R . . . . . H171 H -0.1453 0.2217 0.2894 0.0792 1.0000 Uiso R . . . . . H181 H -0.1321 0.2766 0.3922 0.0912 1.0000 Uiso R . . . . . H191 H 0.0445 0.2523 0.4816 0.1061 1.0000 Uiso R . . . . . H201 H 0.2163 0.1707 0.4669 0.0853 1.0000 Uiso R . . . . . H221 H 0.2131 0.2255 0.1522 0.0592 1.0000 Uiso R . . . . . H231 H 0.0524 0.3151 0.1496 0.0722 1.0000 Uiso R . . . . . H241 H 0.0505 0.3825 0.2444 0.0672 1.0000 Uiso R . . . . . H251 H 0.2047 0.3604 0.3429 0.0631 1.0000 Uiso R . . . . . H261 H 0.3710 0.2739 0.3469 0.0522 1.0000 Uiso R . . . . . H281 H 0.6378 0.0903 0.2049 0.0772 1.0000 Uiso R . . . . . H291 H 0.8145 0.1112 0.1386 0.0952 1.0000 Uiso R . . . . . H301 H 0.8411 0.2179 0.0941 0.0922 1.0000 Uiso R . . . . . H311 H 0.6849 0.3047 0.1105 0.0862 1.0000 Uiso R . . . . . H321 H 0.5087 0.2854 0.1771 0.0702 1.0000 Uiso R . . . . . H33 H 0.1773 -0.1550 0.4865 0.0952 1.0000 Uiso 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 C1 0.044(2) 0.045(2) 0.053(3) -0.011(2) -0.004(2) 0.007(2) C2 0.029(2) 0.031(2) 0.065(3) -0.012(2) 0.0001(19) 0.0030(16) C3 0.0258(18) 0.0303(19) 0.044(2) -0.0050(17) 0.0062(17) 0.0019(15) C4 0.038(2) 0.035(2) 0.051(3) 0.0006(19) 0.0082(19) -0.0068(17) C5 0.048(2) 0.037(2) 0.052(3) -0.003(2) 0.002(2) -0.0105(19) C6 0.058(3) 0.038(2) 0.042(2) -0.005(2) 0.002(2) -0.003(2) C7 0.051(2) 0.035(2) 0.049(3) 0.002(2) 0.013(2) -0.0017(19) C8 0.033(2) 0.0283(19) 0.042(2) -0.0015(17) 0.0097(17) -0.0002(16) C9 0.050(2) 0.044(2) 0.035(2) 0.0045(19) 0.0095(19) 0.0118(19) C10 0.057(3) 0.054(3) 0.050(3) 0.001(2) 0.004(2) 0.018(2) C11 0.091(4) 0.053(3) 0.050(3) 0.007(2) 0.000(3) 0.028(3) C12 0.110(5) 0.053(3) 0.060(3) 0.014(3) 0.033(3) 0.018(3) C13 0.094(4) 0.062(3) 0.074(4) 0.016(3) 0.048(3) 0.007(3) C14 0.064(3) 0.050(3) 0.065(3) 0.011(2) 0.027(3) 0.011(2) C15 0.045(2) 0.039(2) 0.049(3) 0.001(2) 0.019(2) 0.0062(19) C16 0.034(2) 0.041(2) 0.072(3) 0.005(2) 0.014(2) -0.0019(19) C17 0.036(2) 0.048(3) 0.101(4) 0.005(3) 0.021(3) 0.007(2) C18 0.060(3) 0.051(3) 0.116(5) 0.012(3) 0.052(4) 0.012(3) C19 0.105(5) 0.066(4) 0.084(4) 0.004(3) 0.051(4) 0.034(3) C20 0.084(4) 0.058(3) 0.059(3) -0.002(2) 0.025(3) 0.026(3) C21 0.0263(19) 0.032(2) 0.056(3) 0.0002(19) 0.0083(19) -0.0057(16) C22 0.039(2) 0.048(3) 0.053(3) 0.006(2) 0.006(2) 0.0001(19) C23 0.042(2) 0.057(3) 0.065(3) 0.022(3) 0.002(2) 0.004(2) C24 0.039(2) 0.046(3) 0.083(4) 0.009(3) 0.011(3) 0.010(2) C25 0.043(2) 0.034(2) 0.076(3) -0.008(2) 0.009(2) 0.0099(19) C26 0.039(2) 0.029(2) 0.058(3) -0.0072(19) -0.001(2) 0.0035(17) C27 0.042(2) 0.031(2) 0.076(3) -0.003(2) 0.022(2) -0.0080(18) C28 0.056(3) 0.041(3) 0.095(4) 0.000(3) 0.038(3) 0.002(2) C29 0.069(3) 0.050(3) 0.120(5) -0.006(3) 0.060(3) 0.001(3) C30 0.072(3) 0.052(3) 0.104(4) -0.010(3) 0.049(3) -0.017(3) C31 0.075(4) 0.044(3) 0.099(4) 0.001(3) 0.044(3) -0.015(3) C32 0.057(3) 0.032(2) 0.091(4) -0.001(2) 0.034(3) -0.004(2) C33 0.042(3) 0.044(3) 0.187(7) 0.024(4) 0.033(4) -0.003(2) C34 0.047(3) 0.051(3) 0.046(3) -0.001(2) 0.006(2) -0.002(2) P1 0.0354(5) 0.0386(6) 0.0429(6) -0.0026(5) 0.0080(5) 0.0043(5) P2 0.0313(5) 0.0288(5) 0.0583(7) -0.0034(5) 0.0117(5) -0.0023(4) S1 0.0477(7) 0.0338(6) 0.1596(16) -0.0056(8) 0.0117(8) -0.0005(6) S2 0.0389(6) 0.0402(6) 0.0565(7) 0.0078(5) 0.0060(5) -0.0041(5) O1 0.0318(17) 0.049(2) 0.166(4) -0.013(2) 0.012(2) 0.0020(14) O2 0.117(4) 0.060(3) 0.149(4) 0.012(3) 0.040(3) 0.029(2) O3 0.058(2) 0.039(2) 0.249(6) -0.016(3) -0.028(3) -0.0102(18) O4 0.0425(17) 0.074(2) 0.063(2) 0.0088(17) -0.0114(15) -0.0046(16) O5 0.056(2) 0.102(3) 0.052(2) 0.032(2) 0.0116(16) -0.0108(19) O6 0.068(2) 0.0365(17) 0.122(3) -0.0075(19) 0.026(2) 0.0031(16) F1 0.0427(16) 0.0514(18) 0.226(4) 0.030(2) 0.045(2) 0.0093(14) F2 0.065(2) 0.093(3) 0.204(5) -0.055(3) 0.051(3) -0.009(2) F3 0.098(3) 0.115(3) 0.213(5) 0.054(3) 0.073(3) 0.041(3) F4 0.0745(19) 0.0612(17) 0.0632(18) 0.0188(14) 0.0302(14) 0.0041(14) F5 0.102(2) 0.0436(16) 0.091(2) -0.0155(15) 0.0352(19) -0.0027(16) F6 0.0592(18) 0.079(2) 0.084(2) 0.0054(17) -0.0034(15) -0.0262(15) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.542(6) yes C1 . P1 . 1.807(4) yes C1 . H11 . 0.970 no C1 . H12 . 0.978 no C2 . P2 . 1.782(4) yes C2 . H21 . 0.978 no C2 . H22 . 0.972 no C3 . C4 . 1.391(5) yes C3 . C8 . 1.423(5) yes C3 . P1 . 1.781(4) yes C4 . C5 . 1.370(6) yes C4 . H41 . 0.940 no C5 . C6 . 1.377(6) yes C5 . H51 . 0.936 no C6 . C7 . 1.383(6) yes C6 . H61 . 0.934 no C7 . C8 . 1.391(6) yes C7 . H71 . 0.932 no C8 . P2 . 1.784(4) yes C9 . C10 . 1.399(6) yes C9 . C14 . 1.388(6) yes C9 . P1 . 1.780(4) yes C10 . C11 . 1.389(7) yes C10 . H101 . 0.933 no C11 . C12 . 1.368(8) yes C11 . H111 . 0.940 no C12 . C13 . 1.375(8) yes C12 . H33 . 0.941 no C13 . C14 . 1.387(7) yes C13 . H131 . 0.941 no C14 . H141 . 0.936 no C15 . C16 . 1.376(6) yes C15 . C20 . 1.391(7) yes C15 . P1 . 1.781(4) yes C16 . C17 . 1.389(6) yes C16 . H161 . 0.932 no C17 . C18 . 1.375(8) yes C17 . H171 . 0.936 no C18 . C19 . 1.373(8) yes C18 . H181 . 0.928 no C19 . C20 . 1.389(7) yes C19 . H191 . 0.942 no C20 . H201 . 0.941 no C21 . C22 . 1.395(6) yes C21 . C26 . 1.390(6) yes C21 . P2 . 1.777(4) yes C22 . C23 . 1.379(6) yes C22 . H221 . 0.940 no C23 . C24 . 1.370(7) yes C23 . H231 . 0.938 no C24 . C25 . 1.372(7) yes C24 . H241 . 0.941 no C25 . C26 . 1.381(6) yes C25 . H251 . 0.932 no C26 . H261 . 0.935 no C27 . C28 . 1.403(6) yes C27 . C32 . 1.386(6) yes C27 . P2 . 1.776(4) yes C28 . C29 . 1.383(7) yes C28 . H281 . 0.941 no C29 . C30 . 1.371(7) yes C29 . H291 . 0.934 no C30 . C31 . 1.384(7) yes C30 . H301 . 0.939 no C31 . C32 . 1.394(7) yes C31 . H311 . 0.928 no C32 . H321 . 0.932 no C33 . S1 . 1.798(7) yes C33 . F1 . 1.346(6) yes C33 . F2 . 1.317(7) yes C33 . F3 . 1.336(8) yes C34 . S2 . 1.794(5) yes C34 . F4 . 1.333(5) yes C34 . F5 . 1.337(5) yes C34 . F6 . 1.336(5) yes S1 . O1 . 1.433(4) yes S1 . O2 . 1.421(5) yes S1 . O3 . 1.429(4) yes S2 . O4 . 1.429(3) yes S2 . O5 . 1.441(3) yes S2 . O6 . 1.436(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . P1 . 118.5(3) yes C2 . C1 . H11 . 107.1 no P1 . C1 . H11 . 107.1 no C2 . C1 . H12 . 107.8 no P1 . C1 . H12 . 107.2 no H11 . C1 . H12 . 108.9 no C1 . C2 . P2 . 118.6(3) yes C1 . C2 . H21 . 108.0 no P2 . C2 . H21 . 107.6 no C1 . C2 . H22 . 107.2 no P2 . C2 . H22 . 105.1 no H21 . C2 . H22 . 110.3 no C4 . C3 . C8 . 118.3(4) yes C4 . C3 . P1 . 119.1(3) yes C8 . C3 . P1 . 122.6(3) yes C3 . C4 . C5 . 121.5(4) yes C3 . C4 . H41 . 118.6 no C5 . C4 . H41 . 119.9 no C4 . C5 . C6 . 120.4(4) yes C4 . C5 . H51 . 120.0 no C6 . C5 . H51 . 119.5 no C5 . C6 . C7 . 119.8(4) yes C5 . C6 . H61 . 119.7 no C7 . C6 . H61 . 120.5 no C6 . C7 . C8 . 120.9(4) yes C6 . C7 . H71 . 120.6 no C8 . C7 . H71 . 118.5 no C3 . C8 . C7 . 119.1(3) yes C3 . C8 . P2 . 120.1(3) yes C7 . C8 . P2 . 120.7(3) yes C10 . C9 . C14 . 119.5(4) yes C10 . C9 . P1 . 120.3(3) yes C14 . C9 . P1 . 119.9(3) yes C9 . C10 . C11 . 119.3(5) yes C9 . C10 . H101 . 119.0 no C11 . C10 . H101 . 121.7 no C10 . C11 . C12 . 121.0(5) yes C10 . C11 . H111 . 118.8 no C12 . C11 . H111 . 120.2 no C11 . C12 . C13 . 119.7(5) yes C11 . C12 . H33 . 119.9 no C13 . C12 . H33 . 120.0 no C12 . C13 . C14 . 120.7(5) yes C12 . C13 . H131 . 120.2 no C14 . C13 . H131 . 119.1 no C9 . C14 . C13 . 119.8(5) yes C9 . C14 . H141 . 119.2 no C13 . C14 . H141 . 121.0 no C16 . C15 . C20 . 119.2(4) yes C16 . C15 . P1 . 121.5(3) yes C20 . C15 . P1 . 119.3(4) yes C15 . C16 . C17 . 120.6(5) yes C15 . C16 . H161 . 120.4 no C17 . C16 . H161 . 119.0 no C16 . C17 . C18 . 119.4(5) yes C16 . C17 . H171 . 120.6 no C18 . C17 . H171 . 120.0 no C17 . C18 . C19 . 121.2(5) yes C17 . C18 . H181 . 119.3 no C19 . C18 . H181 . 119.5 no C18 . C19 . C20 . 119.2(6) yes C18 . C19 . H191 . 119.9 no C20 . C19 . H191 . 120.9 no C15 . C20 . C19 . 120.5(5) yes C15 . C20 . H201 . 119.7 no C19 . C20 . H201 . 119.9 no C22 . C21 . C26 . 120.1(4) yes C22 . C21 . P2 . 118.3(3) yes C26 . C21 . P2 . 121.5(3) yes C21 . C22 . C23 . 119.3(4) yes C21 . C22 . H221 . 120.0 no C23 . C22 . H221 . 120.7 no C22 . C23 . C24 . 120.4(4) yes C22 . C23 . H231 . 119.9 no C24 . C23 . H231 . 119.6 no C23 . C24 . C25 . 120.4(4) yes C23 . C24 . H241 . 120.1 no C25 . C24 . H241 . 119.5 no C24 . C25 . C26 . 120.6(5) yes C24 . C25 . H251 . 119.7 no C26 . C25 . H251 . 119.7 no C21 . C26 . C25 . 119.1(4) yes C21 . C26 . H261 . 120.4 no C25 . C26 . H261 . 120.4 no C28 . C27 . C32 . 120.0(4) yes C28 . C27 . P2 . 118.8(3) yes C32 . C27 . P2 . 121.0(3) yes C27 . C28 . C29 . 119.0(5) yes C27 . C28 . H281 . 119.6 no C29 . C28 . H281 . 121.4 no C28 . C29 . C30 . 120.9(5) yes C28 . C29 . H291 . 119.4 no C30 . C29 . H291 . 119.7 no C29 . C30 . C31 . 120.7(5) yes C29 . C30 . H301 . 119.9 no C31 . C30 . H301 . 119.4 no C30 . C31 . C32 . 119.4(5) yes C30 . C31 . H311 . 120.7 no C32 . C31 . H311 . 120.0 no C31 . C32 . C27 . 120.1(4) yes C31 . C32 . H321 . 120.3 no C27 . C32 . H321 . 119.6 no S1 . C33 . F1 . 111.9(6) yes S1 . C33 . F2 . 113.2(4) yes F1 . C33 . F2 . 105.6(4) yes S1 . C33 . F3 . 111.2(4) yes F1 . C33 . F3 . 105.6(4) yes F2 . C33 . F3 . 108.9(7) yes S2 . C34 . F4 . 112.5(3) yes S2 . C34 . F5 . 113.3(3) yes F4 . C34 . F5 . 105.7(4) yes S2 . C34 . F6 . 112.1(3) yes F4 . C34 . F6 . 105.9(4) yes F5 . C34 . F6 . 106.8(4) yes C1 . P1 . C15 . 109.2(2) yes C1 . P1 . C3 . 109.83(19) yes C15 . P1 . C3 . 109.22(19) yes C1 . P1 . C9 . 110.5(2) yes C15 . P1 . C9 . 110.10(19) yes C3 . P1 . C9 . 107.95(19) yes C8 . P2 . C2 . 107.32(19) yes C8 . P2 . C21 . 107.48(17) yes C2 . P2 . C21 . 112.8(2) yes C8 . P2 . C27 . 110.66(19) yes C2 . P2 . C27 . 107.2(2) yes C21 . P2 . C27 . 111.3(2) yes C33 . S1 . O1 . 103.6(3) yes C33 . S1 . O2 . 103.0(3) yes O1 . S1 . O2 . 114.2(3) yes C33 . S1 . O3 . 103.0(3) yes O1 . S1 . O3 . 113.2(2) yes O2 . S1 . O3 . 117.4(4) yes C34 . S2 . O4 . 103.9(2) yes C34 . S2 . O5 . 102.5(2) yes O4 . S2 . O5 . 115.0(2) yes C34 . S2 . O6 . 102.2(2) yes O4 . S2 . O6 . 116.3(2) yes O5 . S2 . O6 . 114.2(2) yes data_compound5 _database_code_depnum_ccdc_archive 'CCDC 710850' _audit_creation_date 04-25-05 _audit_creation_method CRYSTALS_ver_12-03-99 _chemical_name_systematic # IUPAC name, in full ; ? ; _chemical_melting_point ? # choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse' _refine_ls_matrix_type full # choose from 'heavy, direct, difmap, geom' _atom_sites_solution_primary direct # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom # choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed' _refine_ls_hydrogen_treatment refU #**************************************************************************** # General computing #============================================================= _computing_structure_refinement ; CRYSTALS (Watkin et al 2003) ; _computing_publication_material ; CRYSTALS (Watkin et al 2003) ; _computing_molecular_graphics ; CAMERON (Watkin et al 1996) ; #============================================================= _cell_length_a 16.1216(9) _cell_angle_alpha 90 _cell_length_b 16.4811(14) _cell_angle_beta 101.602(7) _cell_length_c 26.8178(15) _cell_angle_gamma 90 _cell_volume 6979.9(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 # choose from: rm (reference molecule of # known chirality), ad (anomolous # dispersion - ie. Flack param), rmad # (both rm and ad), syn (known from # synthetic pathway), unk (unknown) # or . (not applicable). _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 International_Tables_Vol_IV_Table_2.2B 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 International_Tables_Vol_IV_Table_2.2B 'P ' 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 International_Tables_Vol_IV_Table_2.2B 'I ' -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 International_Tables_Vol_IV_Table_2.2B 'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 International_Tables_Vol_IV_Table_2.2B 'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 International_Tables_Vol_IV_Table_2.2B _cell_formula_units_Z 8 _chemical_formula_sum ' C36 H36 I2 O1 P2 ' _chemical_formula_moiety ' C33 H30 P2, C3 H6 O, 2(I) ' _chemical_compound_source ; ? ; _chemical_formula_weight 800.39 _cell_measurement_reflns_used 7995 _cell_measurement_theta_min 2.05 _cell_measurement_theta_max 26.06 _cell_measurement_temperature 180 _exptl_crystal_description ' block ' _exptl_crystal_colour ' colorless ' _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_max 0.22 _exptl_crystal_density_diffrn 1.523 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 3168 _exptl_absorpt_coefficient_mu 1.920 _diffrn_measurement_device_type ; Stoe IPDS ; _diffrn_radiation_monochromator graphite _computing_data_collection ; IPDS (Stoe & Cie, 1996) ; _computing_data_reduction ; XRED (Stoe & Cie 1996) ; _computing_cell_refinement ; IPDS (Stoe & Cie, 1996) ; _computing_structure_solution ; SIR92 (Altomare et al, 1994) ; _diffrn_measurement_method '\f scans' _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. r.h. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.75 # Sheldrick geometric definitions 0.72 0.75 _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 180 _diffrn_reflns_number 69932 _reflns_number_total 13133 _diffrn_reflns_av_R_equivalents 0.03 # Number of reflections with Friedels Law is 13133 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 13808 _diffrn_reflns_theta_min 2.048 _diffrn_reflns_theta_max 26.059 _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 26.059 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min -19 _reflns_limit_h_max 19 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 33 _refine_diff_density_min -0.56 _refine_diff_density_max 1.25 _refine_ls_number_reflns 7431 _refine_ls_number_restraints 0 _refine_ls_number_parameters 700 #_refine_ls_R_factor_ref 0.0249 _refine_ls_wR_factor_ref 0.0289 _refine_ls_goodness_of_fit_ref 1.1382 #_reflns_number_all 13082 _refine_ls_R_factor_all 0.0493 _refine_ls_wR_factor_all 0.0327 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>3.00u(I) _reflns_number_gt 7431 _refine_ls_R_factor_gt 0.0249 _refine_ls_wR_factor_gt 0.0289 _refine_ls_shift/su_max 0.001789 _refine_ls_structure_factor_coef F _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 1.08 -0.167 0.707 ; _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 ## -------------------REFERENCES ----------------------## ## Insert your own references - in alphabetic order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Stoe & Cie (1996), IPDS Software Stoe & Cie (1996), XRED V1.08 Watkin D.J. (1994), Acta Cryst, A50, 411-437 Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical Crystallography Laboratory, OXFORD, UK. ; # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 # Replace trailing . with the number of unfound # hydrogen atoms attaced to relavent atom 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_disorder_assembly _atom_site_refinement_disorder_group _atom_site_attached_hydrogens I1 I 0.41085(2) 0.511590(19) 0.330584(10) 0.0409 1.0000 Uani . . . . . . I2 I 0.571677(18) 0.318123(18) 0.153154(11) 0.0367 1.0000 Uani . . . . . . I3 I 0.636668(18) 0.123040(17) 0.393754(11) 0.0361 1.0000 Uani . . . . . . I4 I 0.360106(19) 0.734710(17) 0.114765(12) 0.0400 1.0000 Uani . . . . . . P1 P 0.29647(6) 0.46412(6) 0.07933(4) 0.0240 1.0000 Uani . . . . . . P2 P 0.18694(6) 0.55327(6) 0.17228(4) 0.0247 1.0000 Uani . . . . . . P3 P 0.68744(7) 0.39093(6) 0.40054(4) 0.0284 1.0000 Uani . . . . . . P4 P 0.80486(6) 0.28730(6) 0.31672(4) 0.0246 1.0000 Uani . . . . . . C1 C 0.3757(2) 0.4929(2) 0.13320(15) 0.0275 1.0000 Uani . . . . . . C2 C 0.3517(2) 0.4854(2) 0.18521(14) 0.0278 1.0000 Uani . . . . . . C3 C 0.2984(2) 0.5564(2) 0.19745(14) 0.0278 1.0000 Uani . . . . . . C4 C 0.1581(2) 0.5605(2) 0.10326(14) 0.0252 1.0000 Uani . . . . . . C5 C 0.0821(3) 0.6012(3) 0.08579(16) 0.0344 1.0000 Uani . . . . . . C6 C 0.0465(3) 0.6056(3) 0.03405(17) 0.0395 1.0000 Uani . . . . . . C7 C 0.0864(3) 0.5693(3) -0.00024(16) 0.0369 1.0000 Uani . . . . . . C8 C 0.1628(3) 0.5290(3) 0.01602(15) 0.0323 1.0000 Uani . . . . . . C9 C 0.1999(2) 0.5244(2) 0.06759(14) 0.0261 1.0000 Uani . . . . . . C10 C 0.3440(2) 0.4761(2) 0.02497(14) 0.0265 1.0000 Uani . . . . . . C11 C 0.3786(3) 0.5518(3) 0.01732(16) 0.0352 1.0000 Uani . . . . . . C12 C 0.4107(3) 0.5652(3) -0.02607(17) 0.0385 1.0000 Uani . . . . . . C13 C 0.4090(3) 0.5034(3) -0.06129(16) 0.0409 1.0000 Uani . . . . . . C14 C 0.3756(3) 0.4294(3) -0.05337(17) 0.0435 1.0000 Uani . . . . . . C15 C 0.3423(3) 0.4149(3) -0.01038(16) 0.0342 1.0000 Uani . . . . . . C16 C 0.2672(3) 0.3611(2) 0.08823(14) 0.0282 1.0000 Uani . . . . . . C17 C 0.3306(3) 0.3030(3) 0.10172(17) 0.0386 1.0000 Uani . . . . . . C18 C 0.3086(4) 0.2247(3) 0.11335(19) 0.0491 1.0000 Uani . . . . . . C19 C 0.2253(4) 0.2045(3) 0.1114(2) 0.0546 1.0000 Uani . . . . . . C20 C 0.1624(4) 0.2615(3) 0.0979(2) 0.0573 1.0000 Uani . . . . . . C21 C 0.1824(3) 0.3392(3) 0.0859(2) 0.0436 1.0000 Uani . . . . . . C22 C 0.1437(3) 0.4610(2) 0.19129(16) 0.0310 1.0000 Uani . . . . . . C23 C 0.0684(3) 0.4297(3) 0.16301(19) 0.0480 1.0000 Uani . . . . . . C24 C 0.0381(4) 0.3563(4) 0.1783(3) 0.0693 1.0000 Uani . . . . . . C25 C 0.0810(4) 0.3181(4) 0.2215(3) 0.0773 1.0000 Uani . . . . . . C26 C 0.1516(4) 0.3503(4) 0.2504(3) 0.0783 1.0000 Uani . . . . . . C27 C 0.1848(3) 0.4225(3) 0.2357(2) 0.0510 1.0000 Uani . . . . . . C28 C 0.1419(3) 0.6375(2) 0.19951(16) 0.0322 1.0000 Uani . . . . . . C29 C 0.1591(3) 0.7159(3) 0.1858(2) 0.0485 1.0000 Uani . . . . . . C30 C 0.1281(4) 0.7810(3) 0.2095(3) 0.0636 1.0000 Uani . . . . . . C31 C 0.0808(3) 0.7674(4) 0.2462(2) 0.0588 1.0000 Uani . . . . . . C32 C 0.0629(3) 0.6904(4) 0.2591(2) 0.0538 1.0000 Uani . . . . . . C33 C 0.0937(3) 0.6247(3) 0.23621(17) 0.0423 1.0000 Uani . . . . . . C41 C 0.6101(3) 0.3540(2) 0.34786(15) 0.0312 1.0000 Uani . . . . . . C42 C 0.6381(2) 0.3499(2) 0.29664(14) 0.0283 1.0000 Uani . . . . . . C43 C 0.6932(3) 0.2764(2) 0.29173(15) 0.0295 1.0000 Uani . . . . . . C44 C 0.8333(2) 0.2989(2) 0.38522(15) 0.0268 1.0000 Uani . . . . . . C45 C 0.9151(3) 0.2717(2) 0.40620(15) 0.0312 1.0000 Uani . . . . . . C46 C 0.9478(3) 0.2752(3) 0.45761(17) 0.0386 1.0000 Uani . . . . . . C47 C 0.8991(3) 0.3043(3) 0.49079(16) 0.0405 1.0000 Uani . . . . . . C48 C 0.8174(3) 0.3319(3) 0.47070(16) 0.0366 1.0000 Uani . . . . . . C49 C 0.7837(3) 0.3318(2) 0.41853(14) 0.0291 1.0000 Uani . . . . . . C50 C 0.7215(3) 0.4906(3) 0.38551(16) 0.0344 1.0000 Uani . . . . . . C51 C 0.8059(3) 0.5126(3) 0.3956(2) 0.0481 1.0000 Uani . . . . . . C52 C 0.8287(4) 0.5887(3) 0.3812(3) 0.0639 1.0000 Uani . . . . . . C53 C 0.7685(4) 0.6424(3) 0.3579(2) 0.0611 1.0000 Uani . . . . . . C54 C 0.6847(4) 0.6213(3) 0.3493(2) 0.0582 1.0000 Uani . . . . . . C55 C 0.6599(3) 0.5453(3) 0.36265(19) 0.0472 1.0000 Uani . . . . . . C56 C 0.6344(3) 0.3957(3) 0.45301(16) 0.0334 1.0000 Uani . . . . . . C57 C 0.6449(3) 0.4623(3) 0.48583(16) 0.0377 1.0000 Uani . . . . . . C58 C 0.6022(3) 0.4649(3) 0.52584(17) 0.0435 1.0000 Uani . . . . . . C59 C 0.5499(3) 0.4032(3) 0.53299(18) 0.0481 1.0000 Uani . . . . . . C60 C 0.5391(4) 0.3367(3) 0.5006(2) 0.0549 1.0000 Uani . . . . . . C61 C 0.5818(4) 0.3329(3) 0.46056(19) 0.0492 1.0000 Uani . . . . . . C62 C 0.8544(2) 0.1955(2) 0.30063(14) 0.0271 1.0000 Uani . . . . . . C63 C 0.8213(3) 0.1214(3) 0.31137(17) 0.0367 1.0000 Uani . . . . . . C64 C 0.8588(3) 0.0503(3) 0.29897(19) 0.0397 1.0000 Uani . . . . . . C65 C 0.9285(3) 0.0546(3) 0.27654(18) 0.0392 1.0000 Uani . . . . . . C66 C 0.9621(3) 0.1281(3) 0.26642(19) 0.0434 1.0000 Uani . . . . . . C67 C 0.9252(3) 0.2000(3) 0.27890(17) 0.0371 1.0000 Uani . . . . . . C68 C 0.8440(2) 0.3724(2) 0.28640(15) 0.0288 1.0000 Uani . . . . . . C69 C 0.8092(3) 0.3880(3) 0.23548(16) 0.0357 1.0000 Uani . . . . . . C70 C 0.8390(3) 0.4522(3) 0.21139(18) 0.0426 1.0000 Uani . . . . . . C71 C 0.9027(3) 0.5015(3) 0.2373(2) 0.0480 1.0000 Uani . . . . . . C72 C 0.9374(4) 0.4862(3) 0.2877(2) 0.0550 1.0000 Uani . . . . . . C73 C 0.9086(3) 0.4208(3) 0.31258(17) 0.0422 1.0000 Uani . . . . . . C81 C 0.1661(5) 0.4862(5) 0.3831(3) 0.095(2) 1.0000 Uiso . . . . . . C82 C 0.1060(4) 0.4976(4) 0.4146(3) 0.0724(17) 1.0000 Uiso . . . . . . C83 C 0.1095(6) 0.4492(5) 0.4611(3) 0.097(2) 1.0000 Uiso . . . . . . C84 C 0.7085(7) 0.8292(7) 0.4197(4) 0.125(3) 1.0000 Uiso . . . . . . C85 C 0.6582(4) 0.7674(4) 0.4403(2) 0.0676(16) 1.0000 Uiso . . . . . . C86 C 0.6984(7) 0.7063(7) 0.4775(4) 0.131(3) 1.0000 Uiso . . . . . . O1 O 0.0511(5) 0.5510(4) 0.4026(3) 0.124(2) 1.0000 Uiso . . . . . . O2 O 0.5830(3) 0.7666(3) 0.42614(17) 0.0733(11) 1.0000 Uiso . . . . . . H11 H 0.3908 0.5510 0.1285 0.073(2) 1.0000 Uiso . . . . . . H12 H 0.4266 0.4580 0.1334 0.073(2) 1.0000 Uiso . . . . . . H21 H 0.4049 0.4827 0.2119 0.073(2) 1.0000 Uiso . . . . . . H22 H 0.3187 0.4341 0.1859 0.073(2) 1.0000 Uiso . . . . . . H31 H 0.3210 0.6068 0.1842 0.073(2) 1.0000 Uiso . . . . . . H32 H 0.3064 0.5598 0.2354 0.073(2) 1.0000 Uiso . . . . . . H51 H 0.0526 0.6276 0.1109 0.073(2) 1.0000 Uiso . . . . . . H61 H -0.0082 0.6353 0.0221 0.073(2) 1.0000 Uiso . . . . . . H71 H 0.0608 0.5720 -0.0374 0.073(2) 1.0000 Uiso . . . . . . H81 H 0.1915 0.5024 -0.0096 0.073(2) 1.0000 Uiso . . . . . . H111 H 0.3802 0.5959 0.0431 0.073(2) 1.0000 Uiso . . . . . . H121 H 0.4353 0.6192 -0.0318 0.073(2) 1.0000 Uiso . . . . . . H131 H 0.4320 0.5133 -0.0928 0.073(2) 1.0000 Uiso . . . . . . H141 H 0.3753 0.3850 -0.0789 0.073(2) 1.0000 Uiso . . . . . . H151 H 0.3172 0.3609 -0.0051 0.073(2) 1.0000 Uiso . . . . . . H171 H 0.3912 0.3174 0.1030 0.073(2) 1.0000 Uiso . . . . . . H181 H 0.3537 0.1829 0.1232 0.073(2) 1.0000 Uiso . . . . . . H191 H 0.2103 0.1479 0.1198 0.073(2) 1.0000 Uiso . . . . . . H201 H 0.1019 0.2465 0.0972 0.073(2) 1.0000 Uiso . . . . . . H211 H 0.1365 0.3802 0.0754 0.073(2) 1.0000 Uiso . . . . . . H231 H 0.0371 0.4591 0.1324 0.073(2) 1.0000 Uiso . . . . . . H241 H -0.0151 0.3319 0.1578 0.073(2) 1.0000 Uiso . . . . . . H251 H 0.0595 0.2650 0.2316 0.073(2) 1.0000 Uiso . . . . . . H261 H 0.1798 0.3223 0.2824 0.073(2) 1.0000 Uiso . . . . . . H271 H 0.2374 0.4461 0.2566 0.073(2) 1.0000 Uiso . . . . . . H291 H 0.1938 0.7254 0.1594 0.073(2) 1.0000 Uiso . . . . . . H301 H 0.1397 0.8379 0.1996 0.073(2) 1.0000 Uiso . . . . . . H311 H 0.0595 0.8145 0.2636 0.073(2) 1.0000 Uiso . . . . . . H321 H 0.0275 0.6811 0.2852 0.073(2) 1.0000 Uiso . . . . . . H331 H 0.0812 0.5681 0.2461 0.073(2) 1.0000 Uiso . . . . . . H411 H 0.5596 0.3904 0.3437 0.073(2) 1.0000 Uiso . . . . . . H412 H 0.5937 0.2980 0.3565 0.073(2) 1.0000 Uiso . . . . . . H421 H 0.6708 0.4001 0.2925 0.073(2) 1.0000 Uiso . . . . . . H422 H 0.5864 0.3473 0.2688 0.073(2) 1.0000 Uiso . . . . . . H431 H 0.6724 0.2302 0.3100 0.073(2) 1.0000 Uiso . . . . . . H432 H 0.6859 0.2631 0.2547 0.073(2) 1.0000 Uiso . . . . . . H451 H 0.9507 0.2490 0.3831 0.073(2) 1.0000 Uiso . . . . . . H461 H 1.0071 0.2566 0.4711 0.073(2) 1.0000 Uiso . . . . . . H471 H 0.9219 0.3057 0.5283 0.073(2) 1.0000 Uiso . . . . . . H481 H 0.7817 0.3525 0.4945 0.073(2) 1.0000 Uiso . . . . . . H511 H 0.8502 0.4738 0.4131 0.073(2) 1.0000 Uiso . . . . . . H521 H 0.8898 0.6045 0.3878 0.073(2) 1.0000 Uiso . . . . . . H531 H 0.7856 0.6969 0.3472 0.073(2) 1.0000 Uiso . . . . . . H541 H 0.6406 0.6614 0.3334 0.073(2) 1.0000 Uiso . . . . . . H551 H 0.5987 0.5299 0.3557 0.073(2) 1.0000 Uiso . . . . . . H571 H 0.6829 0.5081 0.4805 0.073(2) 1.0000 Uiso . . . . . . H581 H 0.6105 0.5121 0.5498 0.073(2) 1.0000 Uiso . . . . . . H591 H 0.5188 0.4061 0.5617 0.073(2) 1.0000 Uiso . . . . . . H601 H 0.5002 0.2917 0.5059 0.073(2) 1.0000 Uiso . . . . . . H611 H 0.5748 0.2846 0.4376 0.073(2) 1.0000 Uiso . . . . . . H631 H 0.7711 0.1190 0.3281 0.073(2) 1.0000 Uiso . . . . . . H641 H 0.8352 -0.0035 0.3063 0.073(2) 1.0000 Uiso . . . . . . H651 H 0.9551 0.0033 0.2673 0.073(2) 1.0000 Uiso . . . . . . H661 H 1.0126 0.1302 0.2502 0.073(2) 1.0000 Uiso . . . . . . H671 H 0.9495 0.2537 0.2722 0.073(2) 1.0000 Uiso . . . . . . H691 H 0.7629 0.3526 0.2164 0.073(2) 1.0000 Uiso . . . . . . H701 H 0.8145 0.4634 0.1748 0.073(2) 1.0000 Uiso . . . . . . H711 H 0.9233 0.5486 0.2195 0.073(2) 1.0000 Uiso . . . . . . H721 H 0.9834 0.5218 0.3065 0.073(2) 1.0000 Uiso . . . . . . H731 H 0.9342 0.4091 0.3490 0.073(2) 1.0000 Uiso . . . . . . H811 H 0.2055 0.4412 0.3975 0.073(2) 1.0000 Uiso . . . . . . H812 H 0.1989 0.5372 0.3822 0.073(2) 1.0000 Uiso . . . . . . H813 H 0.1360 0.4714 0.3480 0.073(2) 1.0000 Uiso . . . . . . H831 H 0.1574 0.4091 0.4642 0.073(2) 1.0000 Uiso . . . . . . H832 H 0.1195 0.4854 0.4914 0.073(2) 1.0000 Uiso . . . . . . H833 H 0.0552 0.4190 0.4590 0.073(2) 1.0000 Uiso . . . . . . H841 H 0.7695 0.8220 0.4355 0.073(2) 1.0000 Uiso . . . . . . H842 H 0.6894 0.8845 0.4284 0.073(2) 1.0000 Uiso . . . . . . H843 H 0.6995 0.8231 0.3822 0.073(2) 1.0000 Uiso . . . . . . H861 H 0.7610 0.7149 0.4858 0.073(2) 1.0000 Uiso . . . . . . H862 H 0.6756 0.7114 0.5097 0.073(2) 1.0000 Uiso . . . . . . H863 H 0.6858 0.6506 0.4632 0.073(2) 1.0000 Uiso . . . . . . 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 I1 0.04424(17) 0.05068(18) 0.02805(13) -0.00326(12) 0.00778(12) 0.00464(13) I2 0.03263(14) 0.04277(16) 0.03597(14) 0.00726(12) 0.00960(12) 0.00107(12) I3 0.03306(14) 0.04019(15) 0.03858(15) 0.00249(12) 0.01581(12) 0.00061(12) I4 0.04047(16) 0.03254(14) 0.05026(17) 0.00226(13) 0.01724(13) -0.00167(12) P1 0.0232(5) 0.0254(5) 0.0245(5) -0.0015(4) 0.0073(4) 0.0004(4) P2 0.0239(5) 0.0269(5) 0.0256(5) -0.0011(4) 0.0104(4) -0.0009(4) P3 0.0309(5) 0.0291(5) 0.0272(5) -0.0012(4) 0.0105(4) 0.0017(4) P4 0.0254(5) 0.0257(5) 0.0249(5) 0.0004(4) 0.0104(4) -0.0004(4) C1 0.0228(19) 0.028(2) 0.033(2) -0.0005(16) 0.0087(16) 0.0000(15) C2 0.026(2) 0.033(2) 0.0235(18) 0.0014(16) 0.0049(16) 0.0021(16) C3 0.027(2) 0.030(2) 0.0267(19) -0.0014(16) 0.0073(16) -0.0001(16) C4 0.0187(18) 0.028(2) 0.0292(19) 0.0034(15) 0.0067(15) -0.0016(15) C5 0.028(2) 0.042(2) 0.036(2) -0.0001(18) 0.0114(18) 0.0045(18) C6 0.029(2) 0.050(3) 0.039(2) 0.008(2) 0.0046(19) 0.0061(19) C7 0.027(2) 0.047(3) 0.034(2) 0.0055(19) 0.0004(18) -0.0005(19) C8 0.029(2) 0.041(2) 0.029(2) 0.0001(17) 0.0095(17) 0.0001(18) C9 0.0242(19) 0.0254(19) 0.0292(19) 0.0025(15) 0.0066(16) -0.0027(15) C10 0.0225(19) 0.033(2) 0.0240(18) 0.0010(16) 0.0052(16) -0.0002(16) C11 0.041(2) 0.035(2) 0.032(2) 0.0014(17) 0.0112(19) -0.0006(19) C12 0.039(2) 0.040(2) 0.037(2) 0.0078(19) 0.010(2) -0.005(2) C13 0.041(3) 0.054(3) 0.031(2) 0.006(2) 0.015(2) 0.009(2) C14 0.055(3) 0.045(3) 0.035(2) -0.002(2) 0.021(2) 0.007(2) C15 0.036(2) 0.036(2) 0.031(2) -0.0046(17) 0.0082(18) -0.0015(18) C16 0.030(2) 0.029(2) 0.0269(19) -0.0011(16) 0.0071(17) -0.0018(16) C17 0.039(2) 0.033(2) 0.041(2) 0.0022(19) 0.003(2) -0.0015(19) C18 0.063(3) 0.031(2) 0.050(3) 0.002(2) 0.004(2) 0.002(2) C19 0.075(4) 0.032(3) 0.062(3) -0.005(2) 0.026(3) -0.015(3) C20 0.052(3) 0.045(3) 0.083(4) -0.016(3) 0.031(3) -0.021(3) C21 0.036(2) 0.034(2) 0.064(3) -0.009(2) 0.016(2) -0.0029(19) C22 0.033(2) 0.028(2) 0.036(2) -0.0012(17) 0.0181(18) -0.0024(17) C23 0.044(3) 0.051(3) 0.054(3) -0.007(2) 0.022(2) -0.015(2) C24 0.058(4) 0.053(3) 0.106(5) -0.017(3) 0.040(4) -0.029(3) C25 0.066(4) 0.045(3) 0.139(6) 0.023(4) 0.064(5) -0.004(3) C26 0.059(4) 0.069(4) 0.118(6) 0.054(4) 0.046(4) 0.009(3) C27 0.040(3) 0.058(3) 0.059(3) 0.027(3) 0.020(2) 0.006(2) C28 0.025(2) 0.034(2) 0.037(2) -0.0070(18) 0.0060(18) 0.0003(17) C29 0.040(3) 0.033(2) 0.078(4) -0.006(2) 0.026(3) 0.000(2) C30 0.049(3) 0.036(3) 0.106(5) -0.017(3) 0.017(3) 0.002(2) C31 0.029(2) 0.065(4) 0.082(4) -0.041(3) 0.011(3) 0.007(2) C32 0.043(3) 0.069(4) 0.054(3) -0.027(3) 0.021(2) -0.001(3) C33 0.036(2) 0.054(3) 0.041(2) -0.014(2) 0.016(2) -0.001(2) C41 0.027(2) 0.034(2) 0.033(2) -0.0019(17) 0.0079(18) 0.0000(17) C42 0.027(2) 0.030(2) 0.0282(19) 0.0005(16) 0.0067(17) 0.0003(16) C43 0.029(2) 0.034(2) 0.0272(19) -0.0005(16) 0.0094(17) -0.0014(17) C44 0.027(2) 0.0250(19) 0.030(2) 0.0000(15) 0.0099(17) -0.0020(15) C45 0.028(2) 0.035(2) 0.031(2) 0.0004(17) 0.0079(17) 0.0024(17) C46 0.036(2) 0.041(3) 0.037(2) 0.0038(19) 0.003(2) 0.0019(19) C47 0.044(3) 0.044(3) 0.031(2) -0.0007(19) 0.003(2) 0.002(2) C48 0.039(2) 0.041(2) 0.032(2) 0.0005(18) 0.0109(19) 0.0062(19) C49 0.030(2) 0.032(2) 0.0270(19) 0.0023(16) 0.0092(17) 0.0016(17) C50 0.041(2) 0.031(2) 0.035(2) -0.0031(17) 0.0148(19) -0.0028(18) C51 0.041(3) 0.042(3) 0.064(3) -0.003(2) 0.018(2) -0.002(2) C52 0.063(4) 0.048(3) 0.092(4) -0.015(3) 0.041(3) -0.021(3) C53 0.096(5) 0.034(3) 0.057(3) 0.000(2) 0.026(3) -0.016(3) C54 0.077(4) 0.037(3) 0.053(3) 0.005(2) -0.004(3) -0.004(3) C55 0.059(3) 0.031(2) 0.048(3) 0.002(2) 0.001(2) -0.004(2) C56 0.031(2) 0.036(2) 0.036(2) -0.0001(18) 0.0142(18) 0.0054(18) C57 0.038(2) 0.042(2) 0.034(2) -0.0086(19) 0.0077(19) -0.0003(19) C58 0.044(3) 0.053(3) 0.033(2) -0.008(2) 0.007(2) 0.013(2) C59 0.048(3) 0.066(3) 0.035(2) -0.002(2) 0.020(2) 0.010(3) C60 0.068(4) 0.058(3) 0.048(3) -0.005(2) 0.034(3) -0.013(3) C61 0.068(3) 0.042(3) 0.047(3) -0.008(2) 0.034(3) -0.008(2) C62 0.028(2) 0.030(2) 0.0252(19) -0.0028(15) 0.0094(16) -0.0003(16) C63 0.038(2) 0.030(2) 0.046(2) 0.0015(19) 0.017(2) 0.0011(18) C64 0.037(2) 0.030(2) 0.054(3) 0.000(2) 0.015(2) -0.0017(19) C65 0.033(2) 0.036(2) 0.047(3) -0.009(2) 0.006(2) 0.0058(19) C66 0.034(2) 0.045(3) 0.056(3) -0.008(2) 0.021(2) -0.002(2) C67 0.035(2) 0.034(2) 0.048(3) -0.0035(19) 0.021(2) -0.0015(18) C68 0.027(2) 0.027(2) 0.036(2) 0.0030(16) 0.0134(18) 0.0014(16) C69 0.033(2) 0.041(2) 0.035(2) 0.0090(19) 0.0097(18) -0.0008(18) C70 0.038(2) 0.048(3) 0.043(2) 0.015(2) 0.012(2) 0.003(2) C71 0.049(3) 0.044(3) 0.057(3) 0.016(2) 0.024(2) -0.005(2) C72 0.059(3) 0.054(3) 0.053(3) 0.007(2) 0.012(3) -0.026(3) C73 0.045(3) 0.046(3) 0.036(2) 0.005(2) 0.008(2) -0.015(2) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P1 . C16 . 1.792(4) yes P1 . C10 . 1.789(4) yes P1 . C9 . 1.820(4) yes P1 . C1 . 1.790(4) yes P2 . C28 . 1.790(4) yes P2 . C22 . 1.789(4) yes P2 . C4 . 1.820(4) yes P2 . C3 . 1.789(4) yes P3 . C56 . 1.789(4) yes P3 . C50 . 1.804(4) yes P3 . C49 . 1.814(4) yes P3 . C41 . 1.792(4) yes P4 . C68 . 1.798(4) yes P4 . C62 . 1.803(4) yes P4 . C44 . 1.812(4) yes P4 . C43 . 1.799(4) yes C1 . H12 . 1.001 no C1 . H11 . 1.001 no C1 . C2 . 1.525(5) yes C2 . H22 . 1.000 no C2 . H21 . 1.001 no C2 . C3 . 1.527(5) yes C3 . H32 . 1.001 no C3 . H31 . 0.999 no C4 . C9 . 1.408(5) yes C4 . C5 . 1.393(6) yes C5 . H51 . 1.000 no C5 . C6 . 1.393(6) yes C6 . H61 . 1.002 no C6 . C7 . 1.362(6) yes C7 . H71 . 1.001 no C7 . C8 . 1.391(6) yes C8 . H81 . 1.001 no C8 . C9 . 1.394(6) yes C10 . C15 . 1.381(6) yes C10 . C11 . 1.399(6) yes C11 . H111 . 1.000 no C11 . C12 . 1.382(6) yes C12 . H121 . 0.999 no C12 . C13 . 1.385(7) yes C13 . H131 . 1.001 no C13 . C14 . 1.367(7) yes C14 . H141 . 1.001 no C14 . C15 . 1.386(6) yes C15 . H151 . 1.000 no C16 . C21 . 1.403(6) yes C16 . C17 . 1.394(6) yes C17 . H171 . 0.998 no C17 . C18 . 1.390(6) yes C18 . H181 . 0.999 no C18 . C19 . 1.375(8) yes C19 . H191 . 1.000 no C19 . C20 . 1.376(8) yes C20 . H201 . 1.002 no C20 . C21 . 1.375(7) yes C21 . H211 . 1.000 no C22 . C27 . 1.394(6) yes C22 . C23 . 1.394(6) yes C23 . H231 . 0.997 no C23 . C24 . 1.396(8) yes C24 . H241 . 1.004 no C24 . C25 . 1.377(10) yes C25 . H251 . 0.999 no C25 . C26 . 1.349(10) yes C26 . H261 . 0.999 no C26 . C27 . 1.395(7) yes C27 . H271 . 0.997 no C28 . C33 . 1.387(6) yes C28 . C29 . 1.386(6) yes C29 . H291 . 0.998 no C29 . C30 . 1.391(7) yes C30 . H301 . 1.001 no C30 . C31 . 1.380(9) yes C31 . H311 . 1.001 no C31 . C32 . 1.361(9) yes C32 . H321 . 1.001 no C32 . C33 . 1.385(7) yes C33 . H331 . 1.001 no C41 . H412 . 1.000 no C41 . H411 . 1.000 no C41 . C42 . 1.532(6) yes C42 . H422 . 1.002 no C42 . H421 . 0.999 no C42 . C43 . 1.523(6) yes C43 . H432 . 1.000 no C43 . H431 . 0.999 no C44 . C49 . 1.421(5) yes C44 . C45 . 1.400(6) yes C45 . H451 . 0.998 no C45 . C46 . 1.375(6) yes C46 . H461 . 0.999 no C46 . C47 . 1.386(7) yes C47 . H471 . 1.000 no C47 . C48 . 1.396(6) yes C48 . H481 . 1.000 no C48 . C49 . 1.395(6) yes C50 . C55 . 1.389(7) yes C50 . C51 . 1.380(7) yes C51 . H511 . 1.003 no C51 . C52 . 1.384(7) yes C52 . H521 . 0.999 no C52 . C53 . 1.370(9) yes C53 . H531 . 0.998 no C53 . C54 . 1.368(9) yes C54 . H541 . 1.002 no C54 . C55 . 1.384(7) yes C55 . H551 . 1.001 no C56 . C61 . 1.379(6) yes C56 . C57 . 1.395(6) yes C57 . H571 . 1.001 no C57 . C58 . 1.387(6) yes C58 . H581 . 1.001 no C58 . C59 . 1.359(7) yes C59 . H591 . 1.000 no C59 . C60 . 1.386(7) yes C60 . H601 . 1.000 no C60 . C61 . 1.389(7) yes C61 . H611 . 0.999 no C62 . C67 . 1.384(6) yes C62 . C63 . 1.386(6) yes C63 . H631 . 1.000 no C63 . C64 . 1.389(6) yes C64 . H641 . 1.000 no C64 . C65 . 1.380(7) yes C65 . H651 . 1.002 no C65 . C66 . 1.376(7) yes C66 . H661 . 0.998 no C66 . C67 . 1.395(6) yes C67 . H671 . 1.000 no C68 . C73 . 1.386(6) yes C68 . C69 . 1.392(6) yes C69 . H691 . 1.003 no C69 . C70 . 1.376(6) yes C70 . H701 . 0.999 no C70 . C71 . 1.382(7) yes C71 . H711 . 1.002 no C71 . C72 . 1.378(7) yes C72 . H721 . 0.999 no C72 . C73 . 1.396(6) yes C73 . H731 . 1.000 no C81 . H813 . 0.999 no C81 . H812 . 0.996 no C81 . H811 . 1.002 no C81 . C82 . 1.418(10) yes C82 . O1 . 1.243(9) yes C82 . C83 . 1.473(11) yes C83 . H833 . 0.998 no C83 . H832 . 0.995 no C83 . H831 . 1.007 no C84 . H843 . 0.993 no C84 . H842 . 1.004 no C84 . H841 . 0.996 no C84 . C85 . 1.477(12) yes C85 . O2 . 1.194(7) yes C85 . C86 . 1.473(12) yes C86 . H863 . 1.000 no C86 . H862 . 1.007 no C86 . H861 . 0.999 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C16 . P1 . C10 . 112.40(18) yes C16 . P1 . C9 . 107.54(18) yes C10 . P1 . C9 . 106.87(18) yes C16 . P1 . C1 . 107.95(18) yes C10 . P1 . C1 . 105.97(18) yes C9 . P1 . C1 . 116.23(18) yes C28 . P2 . C22 . 109.27(19) yes C28 . P2 . C4 . 108.81(19) yes C22 . P2 . C4 . 108.14(18) yes C28 . P2 . C3 . 106.42(19) yes C22 . P2 . C3 . 109.68(19) yes C4 . P2 . C3 . 114.44(18) yes C56 . P3 . C50 . 110.5(2) yes C56 . P3 . C49 . 109.46(19) yes C50 . P3 . C49 . 105.4(2) yes C56 . P3 . C41 . 105.6(2) yes C50 . P3 . C41 . 109.2(2) yes C49 . P3 . C41 . 116.70(19) yes C68 . P4 . C62 . 109.46(18) yes C68 . P4 . C44 . 109.66(18) yes C62 . P4 . C44 . 107.27(18) yes C68 . P4 . C43 . 108.98(18) yes C62 . P4 . C43 . 106.59(18) yes C44 . P4 . C43 . 114.73(18) yes H12 . C1 . H11 . 109.286 no H12 . C1 . C2 . 107.855 no H11 . C1 . C2 . 107.742 no H12 . C1 . P1 . 107.700 no H11 . C1 . P1 . 107.664 no C2 . C1 . P1 . 116.5(3) yes H22 . C2 . H21 . 109.363 no H22 . C2 . C3 . 108.641 no H21 . C2 . C3 . 108.626 no H22 . C2 . C1 . 108.521 no H21 . C2 . C1 . 108.575 no C3 . C2 . C1 . 113.1(3) yes H32 . C3 . H31 . 109.465 no H32 . C3 . P2 . 107.399 no H31 . C3 . P2 . 107.466 no H32 . C3 . C2 . 107.363 no H31 . C3 . C2 . 107.405 no P2 . C3 . C2 . 117.6(3) yes C9 . C4 . C5 . 118.9(4) yes C9 . C4 . P2 . 127.2(3) yes C5 . C4 . P2 . 113.7(3) yes H51 . C5 . C6 . 119.505 no H51 . C5 . C4 . 119.273 no C6 . C5 . C4 . 121.2(4) yes H61 . C6 . C7 . 120.229 no H61 . C6 . C5 . 120.167 no C7 . C6 . C5 . 119.6(4) yes H71 . C7 . C8 . 119.723 no H71 . C7 . C6 . 119.793 no C8 . C7 . C6 . 120.5(4) yes H81 . C8 . C9 . 119.455 no H81 . C8 . C7 . 119.691 no C9 . C8 . C7 . 120.9(4) yes C8 . C9 . C4 . 118.9(4) yes C8 . C9 . P1 . 112.5(3) yes C4 . C9 . P1 . 128.5(3) yes C15 . C10 . C11 . 120.3(4) yes C15 . C10 . P1 . 121.7(3) yes C11 . C10 . P1 . 117.9(3) yes H111 . C11 . C12 . 120.322 no H111 . C11 . C10 . 120.140 no C12 . C11 . C10 . 119.5(4) yes H121 . C12 . C13 . 120.256 no H121 . C12 . C11 . 119.906 no C13 . C12 . C11 . 119.8(4) yes H131 . C13 . C14 . 120.055 no H131 . C13 . C12 . 119.655 no C14 . C13 . C12 . 120.3(4) yes H141 . C14 . C15 . 119.612 no H141 . C14 . C13 . 119.536 no C15 . C14 . C13 . 120.9(4) yes H151 . C15 . C10 . 120.312 no H151 . C15 . C14 . 120.493 no C10 . C15 . C14 . 119.2(4) yes C21 . C16 . C17 . 119.5(4) yes C21 . C16 . P1 . 121.2(3) yes C17 . C16 . P1 . 119.0(3) yes H171 . C17 . C18 . 120.311 no H171 . C17 . C16 . 120.498 no C18 . C17 . C16 . 119.2(4) yes H181 . C18 . C19 . 119.722 no H181 . C18 . C17 . 119.698 no C19 . C18 . C17 . 120.6(5) yes H191 . C19 . C20 . 119.793 no H191 . C19 . C18 . 119.756 no C20 . C19 . C18 . 120.5(4) yes H201 . C20 . C21 . 119.811 no H201 . C20 . C19 . 120.040 no C21 . C20 . C19 . 120.1(5) yes H211 . C21 . C20 . 120.050 no H211 . C21 . C16 . 119.861 no C20 . C21 . C16 . 120.1(4) yes C27 . C22 . C23 . 120.6(4) yes C27 . C22 . P2 . 119.0(3) yes C23 . C22 . P2 . 120.4(3) yes H231 . C23 . C24 . 120.819 no H231 . C23 . C22 . 120.568 no C24 . C23 . C22 . 118.6(5) yes H241 . C24 . C25 . 120.343 no H241 . C24 . C23 . 119.863 no C25 . C24 . C23 . 119.8(5) yes H251 . C25 . C26 . 119.153 no H251 . C25 . C24 . 119.121 no C26 . C25 . C24 . 121.7(5) yes H261 . C26 . C27 . 120.108 no H261 . C26 . C25 . 119.818 no C27 . C26 . C25 . 120.1(6) yes H271 . C27 . C22 . 120.547 no H271 . C27 . C26 . 120.377 no C22 . C27 . C26 . 119.1(5) yes C33 . C28 . C29 . 120.1(4) yes C33 . C28 . P2 . 120.1(3) yes C29 . C28 . P2 . 119.7(3) yes H291 . C29 . C30 . 120.500 no H291 . C29 . C28 . 120.301 no C30 . C29 . C28 . 119.2(5) yes H301 . C30 . C31 . 120.053 no H301 . C30 . C29 . 119.825 no C31 . C30 . C29 . 120.1(5) yes H311 . C31 . C32 . 119.709 no H311 . C31 . C30 . 119.750 no C32 . C31 . C30 . 120.5(5) yes H321 . C32 . C33 . 119.733 no H321 . C32 . C31 . 119.982 no C33 . C32 . C31 . 120.3(5) yes H331 . C33 . C32 . 120.178 no H331 . C33 . C28 . 120.086 no C32 . C33 . C28 . 119.7(5) yes H412 . C41 . H411 . 109.458 no H412 . C41 . C42 . 107.889 no H411 . C41 . C42 . 107.827 no H412 . C41 . P3 . 107.815 no H411 . C41 . P3 . 107.790 no C42 . C41 . P3 . 116.0(3) yes H422 . C42 . H421 . 109.430 no H422 . C42 . C43 . 108.293 no H421 . C42 . C43 . 108.577 no H422 . C42 . C41 . 108.551 no H421 . C42 . C41 . 108.720 no C43 . C42 . C41 . 113.2(3) yes H432 . C43 . H431 . 109.580 no H432 . C43 . P4 . 107.543 no H431 . C43 . P4 . 107.578 no H432 . C43 . C42 . 107.793 no H431 . C43 . C42 . 107.760 no P4 . C43 . C42 . 116.5(3) yes C49 . C44 . C45 . 118.3(4) yes C49 . C44 . P4 . 128.2(3) yes C45 . C44 . P4 . 113.6(3) yes H451 . C45 . C46 . 119.109 no H451 . C45 . C44 . 118.900 no C46 . C45 . C44 . 122.0(4) yes H461 . C46 . C47 . 119.902 no H461 . C46 . C45 . 119.695 no C47 . C46 . C45 . 120.4(4) yes H471 . C47 . C48 . 120.597 no H471 . C47 . C46 . 120.836 no C48 . C47 . C46 . 118.6(4) yes H481 . C48 . C49 . 118.877 no H481 . C48 . C47 . 118.913 no C49 . C48 . C47 . 122.2(4) yes C48 . C49 . C44 . 118.5(4) yes C48 . C49 . P3 . 113.9(3) yes C44 . C49 . P3 . 126.7(3) yes C55 . C50 . C51 . 120.3(4) yes C55 . C50 . P3 . 117.8(3) yes C51 . C50 . P3 . 121.8(4) yes H511 . C51 . C52 . 120.231 no H511 . C51 . C50 . 120.439 no C52 . C51 . C50 . 119.3(5) yes H521 . C52 . C53 . 119.633 no H521 . C52 . C51 . 119.725 no C53 . C52 . C51 . 120.6(5) yes H531 . C53 . C54 . 120.111 no H531 . C53 . C52 . 120.063 no C54 . C53 . C52 . 119.8(5) yes H541 . C54 . C55 . 119.376 no H541 . C54 . C53 . 119.723 no C55 . C54 . C53 . 120.9(5) yes H551 . C55 . C54 . 120.509 no H551 . C55 . C50 . 120.579 no C54 . C55 . C50 . 118.9(5) yes C61 . C56 . C57 . 119.8(4) yes C61 . C56 . P3 . 119.2(3) yes C57 . C56 . P3 . 121.0(3) yes H571 . C57 . C58 . 119.977 no H571 . C57 . C56 . 120.285 no C58 . C57 . C56 . 119.7(4) yes H581 . C58 . C59 . 119.867 no H581 . C58 . C57 . 119.799 no C59 . C58 . C57 . 120.3(4) yes H591 . C59 . C60 . 119.988 no H591 . C59 . C58 . 119.630 no C60 . C59 . C58 . 120.4(4) yes H601 . C60 . C61 . 119.855 no H601 . C60 . C59 . 120.085 no C61 . C60 . C59 . 120.1(5) yes H611 . C61 . C56 . 120.264 no H611 . C61 . C60 . 120.082 no C56 . C61 . C60 . 119.6(4) yes C67 . C62 . C63 . 121.3(4) yes C67 . C62 . P4 . 119.9(3) yes C63 . C62 . P4 . 118.8(3) yes H631 . C63 . C64 . 120.188 no H631 . C63 . C62 . 120.538 no C64 . C63 . C62 . 119.3(4) yes H641 . C64 . C65 . 120.434 no H641 . C64 . C63 . 120.043 no C65 . C64 . C63 . 119.5(4) yes H651 . C65 . C66 . 119.340 no H651 . C65 . C64 . 119.381 no C66 . C65 . C64 . 121.3(4) yes H661 . C66 . C67 . 120.019 no H661 . C66 . C65 . 120.263 no C67 . C66 . C65 . 119.7(4) yes H671 . C67 . C62 . 120.616 no H671 . C67 . C66 . 120.479 no C62 . C67 . C66 . 118.9(4) yes C73 . C68 . C69 . 120.3(4) yes C73 . C68 . P4 . 121.1(3) yes C69 . C68 . P4 . 118.6(3) yes H691 . C69 . C70 . 120.132 no H691 . C69 . C68 . 120.326 no C70 . C69 . C68 . 119.5(4) yes H701 . C70 . C71 . 119.493 no H701 . C70 . C69 . 119.816 no C71 . C70 . C69 . 120.7(4) yes H711 . C71 . C72 . 120.079 no H711 . C71 . C70 . 119.950 no C72 . C71 . C70 . 120.0(4) yes H721 . C72 . C73 . 119.749 no H721 . C72 . C71 . 120.143 no C73 . C72 . C71 . 120.1(4) yes H731 . C73 . C68 . 120.312 no H731 . C73 . C72 . 120.276 no C68 . C73 . C72 . 119.4(4) yes H813 . C81 . H812 . 109.931 no H813 . C81 . H811 . 109.411 no H812 . C81 . H811 . 109.640 no H813 . C81 . C82 . 109.426 no H812 . C81 . C82 . 109.383 no H811 . C81 . C82 . 109.032 no O1 . C82 . C83 . 120.3(7) yes O1 . C82 . C81 . 118.5(7) yes C83 . C82 . C81 . 121.2(7) yes H833 . C83 . H832 . 110.085 no H833 . C83 . H831 . 109.038 no H832 . C83 . H831 . 109.308 no H833 . C83 . C82 . 109.795 no H832 . C83 . C82 . 109.780 no H831 . C83 . C82 . 108.811 no H843 . C84 . H842 . 109.705 no H843 . C84 . H841 . 110.376 no H842 . C84 . H841 . 109.467 no H843 . C84 . C85 . 109.262 no H842 . C84 . C85 . 108.798 no H841 . C84 . C85 . 109.207 no O2 . C85 . C86 . 119.2(7) yes O2 . C85 . C84 . 119.1(7) yes C86 . C85 . C84 . 121.6(8) yes H863 . C86 . H862 . 108.894 no H863 . C86 . H861 . 109.588 no H862 . C86 . H861 . 108.962 no H863 . C86 . C85 . 109.867 no H862 . C86 . C85 . 109.599 no H861 . C86 . C85 . 109.908 no data_compound6 _database_code_depnum_ccdc_archive 'CCDC 710851' _audit_creation_date 07-07-25 _audit_creation_method CRYSTALS_ver_12.84 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 35.0471(11) _cell_length_b 14.8261(5) _cell_length_c 17.1363(6) _cell_angle_alpha 90 _cell_angle_beta 103.455(3) _cell_angle_gamma 90 _cell_volume 8659.8(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1 ' _symmetry_space_group_name_Hall ? 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 -x,y,-z+1/2 x,-y,z+1/2 -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' P 0.1023 0.0942 6.4345 1.9067 4.1791 27.1570 1.7800 0.5260 1.4908 68.1645 1.1149 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Rh -1.1178 0.9187 19.2957 0.7515 14.3501 8.2176 4.7343 25.8749 1.2892 98.6062 5.3280 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 _chemical_formula_sum 'C38.50 H37 Cl3 F6 O6 P2 S2' _chemical_formula_moiety 'C35 H34 P2, 2(C F3 O3 S), 1.5(C H2 Cl2) ' _chemical_compound_source ? _chemical_formula_weight 942.14 _cell_measurement_reflns_used 7524 _cell_measurement_theta_min 3 _cell_measurement_theta_max 29 _cell_measurement_temperature 180 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.35 _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 3864 _exptl_absorpt_coefficient_mu 0.452 # Sheldrick geometric approximatio 0.91 0.96 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.31.5 (release 28-08-2006 CrysAlis171 .NET) (compiled Aug 28 2006,13:05:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.96 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 180 _diffrn_reflns_number 39956 _reflns_number_total 11562 _diffrn_reflns_av_R_equivalents 0.075 # Number of reflections with Friedels Law is 11562 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 11585 _diffrn_reflns_theta_min 2.746 _diffrn_reflns_theta_max 29.093 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 29.093 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -47 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -47 _reflns_limit_h_max 46 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.54 _refine_diff_density_max 0.66 _refine_ls_number_reflns 4313 _refine_ls_number_restraints 2 _refine_ls_number_parameters 521 #_refine_ls_R_factor_ref 0.0488 _refine_ls_wR_factor_ref 0.0454 _refine_ls_goodness_of_fit_ref 1.1646 #_reflns_number_all 11559 _refine_ls_R_factor_all 0.1401 _refine_ls_wR_factor_all 0.0649 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>1.8\s(I) _reflns_number_gt 4313 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_gt 0.0454 _refine_ls_shift/su_max 0.002679 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 12.2 10.9 10.9 6.38 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C1 C 0.81522(9) 0.5299(2) 0.21562(19) 0.0211 1.0000 Uani . . . . . . C2 C 0.81657(9) 0.6270(2) 0.24514(19) 0.0242 1.0000 Uani . . . . . . C3 C 0.85836(9) 0.6572(2) 0.28578(18) 0.0221 1.0000 Uani . . . . . . C4 C 0.88582(9) 0.5096(2) 0.14170(17) 0.0218 1.0000 Uani . . . . . . C5 C 0.90260(10) 0.4424(2) 0.1042(2) 0.0280 1.0000 Uani . . . . . . C6 C 0.94192(10) 0.4448(3) 0.1030(2) 0.0336 1.0000 Uani . . . . . . C7 C 0.96538(10) 0.5130(3) 0.1402(2) 0.0342 1.0000 Uani . . . . . . C8 C 0.94953(10) 0.5804(3) 0.1783(2) 0.0297 1.0000 Uani . . . . . . C9 C 0.90979(9) 0.5800(2) 0.18094(17) 0.0208 1.0000 Uani . . . . . . C10 C 0.79418(11) 0.6277(3) 0.3130(2) 0.0356 1.0000 Uani . . . . . . C11 C 0.79630(10) 0.6940(2) 0.1805(2) 0.0313 1.0000 Uani . . . . . . C12 C 0.93811(9) 0.7115(2) 0.30775(18) 0.0220 1.0000 Uani . . . . . . C13 C 0.95151(10) 0.6544(2) 0.3724(2) 0.0299 1.0000 Uani . . . . . . C14 C 0.98455(11) 0.6791(3) 0.4315(2) 0.0346 1.0000 Uani . . . . . . C15 C 1.00322(11) 0.7584(3) 0.4245(2) 0.0402 1.0000 Uani . . . . . . C16 C 0.99014(11) 0.8155(3) 0.3604(2) 0.0399 1.0000 Uani . . . . . . C17 C 0.95754(10) 0.7913(2) 0.3016(2) 0.0303 1.0000 Uani . . . . . . C18 C 0.88431(9) 0.7677(2) 0.1611(2) 0.0240 1.0000 Uani . . . . . . C19 C 0.89143(11) 0.7593(3) 0.0854(2) 0.0305 1.0000 Uani . . . . . . C20 C 0.88445(13) 0.8316(3) 0.0331(2) 0.0433 1.0000 Uani . . . . . . C21 C 0.87117(13) 0.9115(3) 0.0562(3) 0.0461 1.0000 Uani . . . . . . C22 C 0.86419(12) 0.9202(3) 0.1322(3) 0.0405 1.0000 Uani . . . . . . C23 C 0.87055(11) 0.8493(2) 0.1848(2) 0.0310 1.0000 Uani . . . . . . C24 C 0.82337(9) 0.3767(2) 0.12049(19) 0.0233 1.0000 Uani . . . . . . C25 C 0.83455(13) 0.3217(3) 0.1864(2) 0.0395 1.0000 Uani . . . . . . C26 C 0.82746(16) 0.2305(3) 0.1787(3) 0.0544 1.0000 Uani . . . . . . C27 C 0.81050(14) 0.1940(3) 0.1050(3) 0.0516 1.0000 Uani . . . . . . C28 C 0.79979(13) 0.2484(3) 0.0393(3) 0.0455 1.0000 Uani . . . . . . C29 C 0.80613(12) 0.3403(3) 0.0458(2) 0.0354 1.0000 Uani . . . . . . C30 C 0.80884(10) 0.5488(2) 0.03865(18) 0.0233 1.0000 Uani . . . . . . C31 C 0.82995(10) 0.5830(2) -0.01330(19) 0.0276 1.0000 Uani . . . . . . C32 C 0.81013(13) 0.6179(3) -0.0864(2) 0.0395 1.0000 Uani . . . . . . C33 C 0.76979(14) 0.6150(3) -0.1086(2) 0.0490 1.0000 Uani . . . . . . C34 C 0.74864(13) 0.5807(3) -0.0570(3) 0.0495 1.0000 Uani . . . . . . C35 C 0.76843(10) 0.5475(3) 0.0167(2) 0.0352 1.0000 Uani . . . . . . P2 P 0.89580(2) 0.67733(6) 0.23121(5) 0.0195 1.0000 Uani . . . . . . P1 P 0.83356(2) 0.49561(6) 0.13059(5) 0.0200 1.0000 Uani . . . . . . C36 C 0.68031(13) 0.5215(3) 0.1778(2) 0.0420 1.0000 Uani . . . . . . C37 C 0.0573(2) 0.3128(5) 0.1700(3) 0.0785 1.0000 Uani . . . . . . C38 C 0.5818(2) 0.3657(5) 1.0096(4) 0.0893 1.0000 Uani . . . . . . C39 C 1.000000(10) 0.0984(6) 0.250000(10) 0.1096 1.0000 Uani S T . . . . Cl1 Cl 0.58162(8) 0.29857(17) 0.92509(14) 0.1243 1.0000 Uani . . . . . . Cl2 Cl 0.54786(7) 0.45001(13) 0.98897(15) 0.1132 1.0000 Uani . . . . . . Cl3 Cl 0.96050(9) 0.03562(15) 0.2584(2) 0.1492 1.0000 Uani . . . . . . F1 F 0.68918(10) 0.5180(2) 0.25775(16) 0.0732 1.0000 Uani . . . . . . F2 F 0.69927(10) 0.59266(17) 0.15870(18) 0.0701 1.0000 Uani . . . . . . F3 F 0.64275(9) 0.5391(2) 0.1540(2) 0.0724 1.0000 Uani . . . . . . F4 F 0.08281(16) 0.2614(3) 0.2090(4) 0.1790 1.0000 Uani . . . . . . F5 F 0.02891(11) 0.2637(3) 0.12672(17) 0.0920 1.0000 Uani . . . . . . F6 F 0.04202(19) 0.3557(4) 0.2262(2) 0.1595 1.0000 Uani . . . . . . S1 S 0.69369(3) 0.41919(6) 0.13476(5) 0.0312 1.0000 Uani . . . . . . S2 S 0.07512(3) 0.39595(6) 0.11139(5) 0.0296 1.0000 Uani . . . . . . O1 O 0.73427(9) 0.4095(2) 0.1728(2) 0.0625 1.0000 Uani . . . . . . O2 O 0.68596(9) 0.44003(19) 0.05070(16) 0.0470 1.0000 Uani . . . . . . O3 O 0.66838(9) 0.35293(19) 0.15549(18) 0.0465 1.0000 Uani . . . . . . O4 O 0.08872(10) 0.3443(2) 0.0545(2) 0.0683 1.0000 Uani . . . . . . O5 O 0.04055(9) 0.4468(2) 0.0784(2) 0.0599 1.0000 Uani . . . . . . O6 O 0.10447(8) 0.44468(19) 0.16730(17) 0.0458 1.0000 Uani . . . . . . H11 H 0.8305 0.4946 0.2595 0.0256 1.0000 Uiso R . . . . . H12 H 0.7882 0.5114 0.2025 0.0258 1.0000 Uiso R . . . . . H31 H 0.8562 0.7136 0.3137 0.0275 1.0000 Uiso R . . . . . H32 H 0.8694 0.6114 0.3259 0.0272 1.0000 Uiso R . . . . . H51 H 0.8868 0.3947 0.0793 0.0342 1.0000 Uiso R . . . . . H61 H 0.9526 0.3996 0.0772 0.0424 1.0000 Uiso R . . . . . H71 H 0.9920 0.5145 0.1388 0.0418 1.0000 Uiso R . . . . . H81 H 0.9653 0.6277 0.2027 0.0370 1.0000 Uiso R . . . . . H101 H 0.7944 0.6876 0.3351 0.0567 1.0000 Uiso R . . . . . H102 H 0.8070 0.5866 0.3541 0.0564 1.0000 Uiso R . . . . . H103 H 0.7679 0.6081 0.2932 0.0567 1.0000 Uiso R . . . . . H111 H 0.7985 0.7533 0.2030 0.0459 1.0000 Uiso R . . . . . H112 H 0.8074 0.6930 0.1356 0.0454 1.0000 Uiso R . . . . . H113 H 0.7693 0.6779 0.1643 0.0449 1.0000 Uiso R . . . . . H131 H 0.9391 0.6003 0.3772 0.0351 1.0000 Uiso R . . . . . H141 H 0.9938 0.6418 0.4751 0.0414 1.0000 Uiso R . . . . . H151 H 1.0255 0.7734 0.4642 0.0479 1.0000 Uiso R . . . . . H161 H 1.0031 0.8701 0.3574 0.0480 1.0000 Uiso R . . . . . H171 H 0.9482 0.8295 0.2582 0.0357 1.0000 Uiso R . . . . . H191 H 0.9007 0.7050 0.0691 0.0366 1.0000 Uiso R . . . . . H201 H 0.8887 0.8263 -0.0187 0.0540 1.0000 Uiso R . . . . . H211 H 0.8665 0.9601 0.0214 0.0560 1.0000 Uiso R . . . . . H221 H 0.8555 0.9737 0.1482 0.0501 1.0000 Uiso R . . . . . H231 H 0.8658 0.8566 0.2352 0.0392 1.0000 Uiso R . . . . . H251 H 0.8468 0.3468 0.2363 0.0478 1.0000 Uiso R . . . . . H261 H 0.8343 0.1931 0.2233 0.0663 1.0000 Uiso R . . . . . H271 H 0.8063 0.1322 0.0995 0.0618 1.0000 Uiso R . . . . . H281 H 0.7878 0.2238 -0.0096 0.0537 1.0000 Uiso R . . . . . H291 H 0.7989 0.3775 0.0023 0.0422 1.0000 Uiso R . . . . . H311 H 0.8572 0.5822 0.0005 0.0330 1.0000 Uiso R . . . . . H321 H 0.8242 0.6428 -0.1207 0.0496 1.0000 Uiso R . . . . . H331 H 0.7568 0.6348 -0.1590 0.0565 1.0000 Uiso R . . . . . H341 H 0.7213 0.5794 -0.0703 0.0567 1.0000 Uiso R . . . . . H351 H 0.7544 0.5235 0.0522 0.0421 1.0000 Uiso R . . . . . H381 H 0.6076 0.3923 1.0266 0.1042 1.0000 Uiso R . . . . . H382 H 0.5764 0.3281 1.0512 0.1044 1.0000 Uiso R . . . . . H391 H 1.0073 0.1346 0.2953 0.1227 1.0000 Uiso 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 C1 0.0204(15) 0.0223(15) 0.0222(15) -0.0014(12) 0.0085(12) -0.0005(12) C2 0.0231(16) 0.0278(18) 0.0248(16) -0.0021(13) 0.0117(13) 0.0012(13) C3 0.0247(17) 0.0225(17) 0.0212(15) -0.0010(12) 0.0093(12) 0.0023(13) C4 0.0181(14) 0.0281(17) 0.0206(15) 0.0023(13) 0.0075(11) 0.0027(13) C5 0.0271(18) 0.0279(18) 0.0299(18) -0.0065(14) 0.0087(14) 0.0019(14) C6 0.0291(19) 0.036(2) 0.041(2) -0.0081(16) 0.0171(16) 0.0065(15) C7 0.0217(17) 0.035(2) 0.049(2) 0.0018(17) 0.0139(15) 0.0034(15) C8 0.0260(18) 0.0294(18) 0.0375(18) -0.0035(15) 0.0156(15) -0.0002(14) C9 0.0218(16) 0.0218(15) 0.0182(15) 0.0002(13) 0.0033(12) 0.0062(13) C10 0.031(2) 0.043(2) 0.040(2) -0.0110(17) 0.0244(16) -0.0091(17) C11 0.0175(16) 0.034(2) 0.0402(19) -0.0012(15) 0.0032(14) 0.0012(14) C12 0.0186(15) 0.0264(16) 0.0210(15) -0.0030(13) 0.0045(12) 0.0014(12) C13 0.0307(19) 0.0297(18) 0.0284(18) 0.0028(14) 0.0052(15) 0.0036(14) C14 0.0298(19) 0.050(2) 0.0226(16) 0.0031(17) 0.0029(14) 0.0083(18) C15 0.0244(18) 0.063(3) 0.0325(19) -0.0044(19) 0.0050(15) -0.0045(18) C16 0.034(2) 0.047(2) 0.039(2) -0.0064(18) 0.0063(16) -0.0115(18) C17 0.0268(18) 0.0305(18) 0.0321(18) 0.0035(15) 0.0040(14) -0.0022(14) C18 0.0206(16) 0.0241(17) 0.0274(17) 0.0054(14) 0.0054(12) 0.0030(13) C19 0.035(2) 0.0313(19) 0.0265(17) 0.0021(14) 0.0100(14) 0.0011(15) C20 0.058(3) 0.046(2) 0.0300(19) 0.0136(18) 0.0193(18) 0.006(2) C21 0.051(3) 0.043(2) 0.045(2) 0.022(2) 0.0135(19) 0.009(2) C22 0.045(2) 0.0281(19) 0.052(2) 0.0090(18) 0.0200(19) 0.0114(17) C23 0.0306(18) 0.0309(18) 0.0361(19) 0.0028(15) 0.0169(15) 0.0070(15) C24 0.0237(16) 0.0180(16) 0.0306(17) -0.0025(13) 0.0111(13) -0.0044(12) C25 0.058(3) 0.0274(19) 0.0342(19) -0.0033(16) 0.0122(17) -0.0047(18) C26 0.091(4) 0.027(2) 0.046(2) 0.0042(19) 0.018(2) -0.003(2) C27 0.066(3) 0.024(2) 0.066(3) -0.011(2) 0.017(2) -0.011(2) C28 0.053(3) 0.038(2) 0.042(2) -0.0157(19) 0.0053(19) -0.007(2) C29 0.044(2) 0.033(2) 0.0295(18) -0.0058(16) 0.0105(16) -0.0051(17) C30 0.0272(17) 0.0243(17) 0.0183(15) -0.0009(13) 0.0048(12) 0.0008(13) C31 0.0277(18) 0.0329(19) 0.0223(16) 0.0034(14) 0.0062(13) 0.0010(15) C32 0.055(3) 0.039(2) 0.0293(19) 0.0103(16) 0.0191(17) 0.0084(19) C33 0.053(3) 0.055(3) 0.032(2) 0.0066(19) -0.0029(18) 0.024(2) C34 0.030(2) 0.067(3) 0.047(2) 0.001(2) -0.0014(18) 0.015(2) C35 0.0264(19) 0.045(2) 0.034(2) 0.0031(17) 0.0065(15) 0.0050(17) P2 0.0186(4) 0.0208(4) 0.0200(4) 0.0001(3) 0.0060(3) 0.0016(3) P1 0.0194(4) 0.0226(4) 0.0186(4) -0.0007(3) 0.0057(3) 0.0000(3) C36 0.054(3) 0.034(2) 0.044(2) -0.0044(17) 0.024(2) -0.0058(19) C37 0.095(4) 0.103(5) 0.030(2) 0.008(3) 0.000(3) -0.057(4) C38 0.070(4) 0.092(5) 0.097(5) 0.021(4) 0.002(3) -0.016(3) C39 0.127(9) 0.044(5) 0.134(9) 0.0000 -0.016(7) 0.0000 Cl1 0.1318(18) 0.1119(16) 0.1244(16) -0.0191(13) 0.0202(14) 0.0315(13) Cl2 0.1246(15) 0.0824(12) 0.1538(19) 0.0228(12) 0.0757(14) 0.0138(11) Cl3 0.172(2) 0.0744(12) 0.196(3) 0.0352(15) 0.033(2) -0.0143(14) F1 0.117(3) 0.0659(19) 0.0437(15) -0.0173(13) 0.0327(16) -0.0191(17) F2 0.108(2) 0.0332(14) 0.0804(19) -0.0096(14) 0.0459(18) -0.0253(15) F3 0.068(2) 0.0583(18) 0.098(2) -0.0128(16) 0.0331(17) 0.0208(15) F4 0.145(4) 0.129(4) 0.192(5) 0.122(4) -0.103(4) -0.084(3) F5 0.104(3) 0.109(3) 0.0534(17) 0.0084(17) -0.0009(17) -0.076(2) F6 0.216(6) 0.223(6) 0.064(2) -0.035(3) 0.081(3) -0.114(5) S1 0.0335(5) 0.0266(4) 0.0352(5) 0.0043(4) 0.0116(4) -0.0014(4) S2 0.0283(4) 0.0335(5) 0.0291(4) -0.0082(4) 0.0108(3) -0.0030(4) O1 0.0380(17) 0.066(2) 0.077(2) 0.0041(18) 0.0006(16) 0.0049(15) O2 0.073(2) 0.0389(16) 0.0345(15) 0.0019(12) 0.0223(14) 0.0053(14) O3 0.0590(19) 0.0316(15) 0.0561(17) 0.0042(13) 0.0279(15) -0.0103(13) O4 0.069(2) 0.065(2) 0.090(2) -0.041(2) 0.057(2) -0.0157(17) O5 0.0371(17) 0.0503(19) 0.082(2) -0.0153(17) -0.0063(16) 0.0047(14) O6 0.0412(16) 0.0465(17) 0.0420(16) -0.0031(13) -0.0057(12) -0.0130(13) _refine_ls_extinction_method None loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 . C2 . 1.524(5) yes C1 . P1 . 1.797(3) yes C1 . H11 . 0.969 no C1 . H12 . 0.961 no C2 . C3 . 1.535(5) yes C2 . C10 . 1.547(4) yes C2 . C11 . 1.534(5) yes C3 . P2 . 1.804(3) yes C3 . H31 . 0.975 no C3 . H32 . 0.980 no C4 . C5 . 1.387(5) yes C4 . C9 . 1.409(5) yes C4 . P1 . 1.809(3) yes C5 . C6 . 1.384(5) yes C5 . H51 . 0.938 no C6 . C7 . 1.364(5) yes C6 . H61 . 0.929 no C7 . C8 . 1.379(5) yes C7 . H71 . 0.940 no C8 . C9 . 1.404(5) yes C8 . H81 . 0.930 no C9 . P2 . 1.805(3) yes C10 . H101 . 0.965 no C10 . H102 . 0.961 no C10 . H103 . 0.951 no C11 . H111 . 0.957 no C11 . H112 . 0.940 no C11 . H113 . 0.953 no C12 . C13 . 1.387(5) yes C12 . C17 . 1.382(5) yes C12 . P2 . 1.809(3) yes C13 . C14 . 1.398(5) yes C13 . H131 . 0.925 no C14 . C15 . 1.364(6) yes C14 . H141 . 0.925 no C15 . C16 . 1.378(6) yes C15 . H151 . 0.934 no C16 . C17 . 1.384(5) yes C16 . H161 . 0.937 no C17 . H171 . 0.932 no C18 . C19 . 1.383(5) yes C18 . C23 . 1.397(5) yes C18 . P2 . 1.782(3) yes C19 . C20 . 1.382(5) yes C19 . H191 . 0.935 no C20 . C21 . 1.364(6) yes C20 . H201 . 0.938 no C21 . C22 . 1.387(6) yes C21 . H211 . 0.924 no C22 . C23 . 1.369(5) yes C22 . H221 . 0.914 no C23 . H231 . 0.923 no C24 . C25 . 1.374(5) yes C24 . C29 . 1.390(5) yes C24 . P1 . 1.799(3) yes C25 . C26 . 1.376(6) yes C25 . H251 . 0.940 no C26 . C27 . 1.375(6) yes C26 . H261 . 0.930 no C27 . C28 . 1.365(6) yes C27 . H271 . 0.928 no C28 . C29 . 1.382(6) yes C28 . H281 . 0.921 no C29 . H291 . 0.916 no C30 . C31 . 1.380(4) yes C30 . C35 . 1.378(5) yes C30 . P1 . 1.794(3) yes C31 . C32 . 1.384(5) yes C31 . H311 . 0.929 no C32 . C33 . 1.377(6) yes C32 . H321 . 0.928 no C33 . C34 . 1.376(7) yes C33 . H331 . 0.925 no C34 . C35 . 1.382(6) yes C34 . H341 . 0.932 no C35 . H351 . 0.936 no C36 . F1 . 1.333(5) yes C36 . F2 . 1.328(5) yes C36 . F3 . 1.311(5) yes C36 . S1 . 1.796(4) yes C37 . F4 . 1.243(8) yes C37 . F5 . 1.315(6) yes C37 . F6 . 1.364(9) yes C37 . S2 . 1.792(5) yes C38 . Cl1 . 1.755(8) yes C38 . Cl2 . 1.706(7) yes C38 . H381 . 0.966 no C38 . H382 . 0.958 no C39 . Cl3 5_755 1.702(5) yes C39 . H391 5_755 0.930 no C39 . Cl3 . 1.702(5) yes C39 . H391 . 0.930 no S1 . O1 . 1.427(3) yes S1 . O2 . 1.436(3) yes S1 . O3 . 1.423(3) yes S2 . O4 . 1.407(3) yes S2 . O5 . 1.427(3) yes S2 . O6 . 1.428(3) yes loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . C1 . P1 . 123.2(2) yes C2 . C1 . H11 . 106.5 no P1 . C1 . H11 . 103.8 no C2 . C1 . H12 . 107.4 no P1 . C1 . H12 . 104.4 no H11 . C1 . H12 . 111.4 no C1 . C2 . C3 . 112.3(3) yes C1 . C2 . C10 . 105.9(3) yes C3 . C2 . C10 . 104.7(3) yes C1 . C2 . C11 . 113.5(3) yes C3 . C2 . C11 . 111.8(3) yes C10 . C2 . C11 . 107.9(3) yes C2 . C3 . P2 . 123.0(2) yes C2 . C3 . H31 . 107.3 no P2 . C3 . H31 . 105.2 no C2 . C3 . H32 . 107.2 no P2 . C3 . H32 . 105.2 no H31 . C3 . H32 . 108.3 no C5 . C4 . C9 . 118.9(3) yes C5 . C4 . P1 . 113.4(2) yes C9 . C4 . P1 . 127.7(2) yes C4 . C5 . C6 . 121.3(3) yes C4 . C5 . H51 . 118.9 no C6 . C5 . H51 . 119.8 no C5 . C6 . C7 . 120.4(3) yes C5 . C6 . H61 . 120.2 no C7 . C6 . H61 . 119.4 no C6 . C7 . C8 . 119.5(3) yes C6 . C7 . H71 . 120.0 no C8 . C7 . H71 . 120.4 no C7 . C8 . C9 . 121.6(3) yes C7 . C8 . H81 . 119.9 no C9 . C8 . H81 . 118.5 no C4 . C9 . C8 . 118.2(3) yes C4 . C9 . P2 . 128.5(2) yes C8 . C9 . P2 . 113.2(3) yes C2 . C10 . H101 . 110.1 no C2 . C10 . H102 . 108.3 no H101 . C10 . H102 . 109.6 no C2 . C10 . H103 . 110.4 no H101 . C10 . H103 . 109.9 no H102 . C10 . H103 . 108.5 no C2 . C11 . H111 . 108.9 no C2 . C11 . H112 . 111.7 no H111 . C11 . H112 . 109.6 no C2 . C11 . H113 . 108.1 no H111 . C11 . H113 . 109.2 no H112 . C11 . H113 . 109.3 no C13 . C12 . C17 . 120.2(3) yes C13 . C12 . P2 . 118.5(3) yes C17 . C12 . P2 . 121.3(2) yes C12 . C13 . C14 . 119.3(3) yes C12 . C13 . H131 . 121.4 no C14 . C13 . H131 . 119.3 no C13 . C14 . C15 . 119.7(3) yes C13 . C14 . H141 . 120.3 no C15 . C14 . H141 . 120.0 no C14 . C15 . C16 . 121.4(4) yes C14 . C15 . H151 . 118.5 no C16 . C15 . H151 . 120.0 no C15 . C16 . C17 . 119.2(4) yes C15 . C16 . H161 . 120.0 no C17 . C16 . H161 . 120.9 no C16 . C17 . C12 . 120.3(3) yes C16 . C17 . H171 . 120.1 no C12 . C17 . H171 . 119.6 no C19 . C18 . C23 . 120.1(3) yes C19 . C18 . P2 . 120.2(3) yes C23 . C18 . P2 . 119.6(3) yes C18 . C19 . C20 . 119.6(3) yes C18 . C19 . H191 . 120.6 no C20 . C19 . H191 . 119.8 no C19 . C20 . C21 . 120.4(3) yes C19 . C20 . H201 . 120.4 no C21 . C20 . H201 . 119.2 no C20 . C21 . C22 . 120.0(4) yes C20 . C21 . H211 . 120.7 no C22 . C21 . H211 . 119.3 no C21 . C22 . C23 . 120.6(4) yes C21 . C22 . H221 . 120.5 no C23 . C22 . H221 . 118.9 no C18 . C23 . C22 . 119.2(3) yes C18 . C23 . H231 . 121.6 no C22 . C23 . H231 . 119.2 no C25 . C24 . C29 . 120.4(3) yes C25 . C24 . P1 . 119.4(3) yes C29 . C24 . P1 . 120.2(3) yes C24 . C25 . C26 . 119.6(4) yes C24 . C25 . H251 . 119.7 no C26 . C25 . H251 . 120.7 no C25 . C26 . C27 . 120.3(4) yes C25 . C26 . H261 . 120.1 no C27 . C26 . H261 . 119.6 no C26 . C27 . C28 . 120.2(4) yes C26 . C27 . H271 . 120.4 no C28 . C27 . H271 . 119.5 no C27 . C28 . C29 . 120.5(4) yes C27 . C28 . H281 . 119.8 no C29 . C28 . H281 . 119.6 no C24 . C29 . C28 . 119.0(4) yes C24 . C29 . H291 . 119.7 no C28 . C29 . H291 . 121.3 no C31 . C30 . C35 . 120.0(3) yes C31 . C30 . P1 . 120.4(3) yes C35 . C30 . P1 . 119.3(3) yes C30 . C31 . C32 . 119.4(3) yes C30 . C31 . H311 . 120.3 no C32 . C31 . H311 . 120.3 no C31 . C32 . C33 . 120.3(4) yes C31 . C32 . H321 . 119.6 no C33 . C32 . H321 . 120.1 no C32 . C33 . C34 . 120.4(4) yes C32 . C33 . H331 . 119.8 no C34 . C33 . H331 . 119.8 no C33 . C34 . C35 . 119.2(4) yes C33 . C34 . H341 . 121.8 no C35 . C34 . H341 . 119.0 no C34 . C35 . C30 . 120.6(4) yes C34 . C35 . H351 . 120.1 no C30 . C35 . H351 . 119.2 no C12 . P2 . C9 . 107.58(14) yes C12 . P2 . C3 . 104.05(15) yes C9 . P2 . C3 . 115.23(15) yes C12 . P2 . C18 . 107.26(15) yes C9 . P2 . C18 . 108.83(15) yes C3 . P2 . C18 . 113.35(15) yes C4 . P1 . C24 . 107.22(15) yes C4 . P1 . C1 . 115.26(14) yes C24 . P1 . C1 . 104.74(14) yes C4 . P1 . C30 . 108.20(15) yes C24 . P1 . C30 . 107.54(15) yes C1 . P1 . C30 . 113.40(15) yes F1 . C36 . F2 . 105.9(3) yes F1 . C36 . F3 . 107.8(4) yes F2 . C36 . F3 . 106.8(4) yes F1 . C36 . S1 . 111.6(3) yes F2 . C36 . S1 . 112.1(3) yes F3 . C36 . S1 . 112.3(3) yes F4 . C37 . F5 . 108.6(6) yes F4 . C37 . F6 . 105.0(5) yes F5 . C37 . F6 . 106.6(5) yes F4 . C37 . S2 . 115.0(5) yes F5 . C37 . S2 . 112.4(3) yes F6 . C37 . S2 . 108.6(5) yes Cl1 . C38 . Cl2 . 112.0(4) yes Cl1 . C38 . H381 . 107.7 no Cl2 . C38 . H381 . 108.7 no Cl1 . C38 . H382 . 108.7 no Cl2 . C38 . H382 . 109.4 no H381 . C38 . H382 . 110.3 no Cl3 5_755 C39 . H391 5_755 108.4 no Cl3 5_755 C39 . Cl3 . 113.7(5) yes H391 5_755 C39 . Cl3 . 108.4 no Cl3 5_755 C39 . H391 . 108.4 no H391 5_755 C39 . H391 . 109.5 no Cl3 . C39 . H391 . 108.4 no C36 . S1 . O1 . 103.0(2) yes C36 . S1 . O2 . 102.97(18) yes O1 . S1 . O2 . 114.5(2) yes C36 . S1 . O3 . 104.06(19) yes O1 . S1 . O3 . 115.4(2) yes O2 . S1 . O3 . 114.58(19) yes C37 . S2 . O4 . 103.4(3) yes C37 . S2 . O5 . 102.2(3) yes O4 . S2 . O5 . 114.0(2) yes C37 . S2 . O6 . 105.2(2) yes O4 . S2 . O6 . 115.6(2) yes O5 . S2 . O6 . 114.24(18) yes data_compound13 _database_code_depnum_ccdc_archive 'CCDC 710852' #============================================================================== _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. and Camalli, M. (1994)., SIR92 program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. 27, 435. Sheldrick, G. M. (1997). SHELXL97. Program for the refinement of Crystal Structures. University of Gottingen, Germany. Stoe, IPDS Manual. Version 2.75. Stoe & Cie, Darmstadt,1996, Germany. Stoe, X-RED, Data Reduction for STADI4 and IPDS, Revision 1.08. Stoe & Cie, Darmstadt, 1996, Germany. MULTI SCAN - c.f. r.h. blessing, acta cryst. (1995), a51, 33-38 WINGX - 1.63 Integrated System of Windows Programs for the Solution, Refinement and Analysis of Single Crystal X-Ray Diffraction Data. Farrugia, L. J. Appl. Crystallogr., 1999, 32, 837. ORTEP3 for Windows, Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565.; ; #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C32 H29 O P2, C4 H8 O, F6 P' _chemical_formula_sum 'C36 H37 F6 O2 P3' _chemical_formula_weight 708.57 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.474(5) _cell_length_b 12.913(5) _cell_length_c 13.705(5) _cell_angle_alpha 110.218(5) _cell_angle_beta 113.218(5) _cell_angle_gamma 91.949(5) _cell_volume 1716.7(12) _cell_formula_units_Z 2 _cell_measurement_temperature 180 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 26.05 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.375 _exptl_crystal_size_mid 0.375 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.238 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details ; (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166) ; _exptl_absorpt_correction_T_min 0.918 _exptl_absorpt_correction_T_max 0.951 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Stoe IPDS' _diffrn_measurement_method \f _diffrn_standards_number 200 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 4 _diffrn_standards_decay_% 0.1 _diffrn_reflns_av_R_equivalents 0.0395 _diffrn_reflns_av_unetI/netI 0.046 _diffrn_reflns_number 17048 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 26.17 _diffrn_reflns_theta_full 26.17 _diffrn_measured_fraction_theta_full 0.916 _diffrn_measured_fraction_theta_max 0.916 _reflns_number_total 6294 _reflns_number_gt 4325 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Stoe IPDS software (Stoe, 1996)' _computing_cell_refinement 'Stoe IPDS software (Stoe, 1996)' _computing_data_reduction 'XRED (Stoe, 1.08, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 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)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.1015P)^2^+0.1144P] 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_number_reflns 6294 _refine_ls_number_parameters 421 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1656 _refine_ls_wR_factor_gt 0.151 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.616 _refine_diff_density_min -0.442 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 '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' 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 1.3706(3) 0.0562(2) 0.2319(3) 0.0381(7) Uani 1 1 d . . . C2 C 1.4069(4) -0.0484(3) 0.1972(3) 0.0526(9) Uani 1 1 d . . . H2 H 1.369 -0.0969 0.1199 0.063 Uiso 1 1 calc R . . C3 C 1.4983(4) -0.0790(3) 0.2774(4) 0.0603(10) Uani 1 1 d . . . H3 H 1.5218 -0.1484 0.2537 0.072 Uiso 1 1 calc R . . C4 C 1.5558(4) -0.0087(3) 0.3924(3) 0.0540(9) Uani 1 1 d . . . H4 H 1.6169 -0.0307 0.446 0.065 Uiso 1 1 calc R . . C5 C 1.5217(3) 0.0956(3) 0.4277(3) 0.0500(8) Uani 1 1 d . . . H5 H 1.5613 0.144 0.5051 0.06 Uiso 1 1 calc R . . C6 C 1.4291(3) 0.1275(3) 0.3483(3) 0.0437(7) Uani 1 1 d . . . H6 H 1.4057 0.1968 0.3727 0.052 Uiso 1 1 calc R . . C7 C 1.3276(3) 0.1689(3) 0.0746(3) 0.0387(7) Uani 1 1 d . . . C8 C 1.4203(3) 0.2655(3) 0.1474(3) 0.0458(7) Uani 1 1 d . . . H8 H 1.4435 0.2934 0.2262 0.055 Uiso 1 1 calc R . . C9 C 1.4794(3) 0.3215(3) 0.1037(3) 0.0534(8) Uani 1 1 d . . . H9 H 1.5422 0.3866 0.1529 0.064 Uiso 1 1 calc R . . C10 C 1.4443(4) 0.2798(3) -0.0135(3) 0.0559(9) Uani 1 1 d . . . H10 H 1.485 0.3166 -0.0426 0.067 Uiso 1 1 calc R . . C11 C 1.3510(4) 0.1857(4) -0.0871(3) 0.0624(10) Uani 1 1 d . . . H11 H 1.3268 0.1596 -0.1659 0.075 Uiso 1 1 calc R . . C12 C 1.2924(4) 0.1293(3) -0.0442(3) 0.0538(9) Uani 1 1 d . . . H12 H 1.2291 0.0646 -0.0943 0.065 Uiso 1 1 calc R . . C13 C 1.1639(3) 0.1786(3) 0.1912(3) 0.0390(7) Uani 1 1 d . . . H13A H 1.1217 0.1384 0.2203 0.047 Uiso 1 1 calc R . . H13B H 1.2265 0.2426 0.2565 0.047 Uiso 1 1 calc R . . C14 C 1.0635(3) 0.2205(2) 0.1097(2) 0.0355(6) Uani 1 1 d . . . H14A H 0.999 0.1566 0.046 0.043 Uiso 1 1 calc R . . H14B H 1.1052 0.2579 0.0782 0.043 Uiso 1 1 calc R . . C15 C 1.1046(3) 0.4344(2) 0.2994(2) 0.0328(6) Uani 1 1 d . . . C16 C 1.0885(3) 0.4897(3) 0.3987(3) 0.0437(7) Uani 1 1 d . . . H16 H 1.0149 0.4658 0.4043 0.052 Uiso 1 1 calc R . . C17 C 1.1813(3) 0.5798(3) 0.4890(3) 0.0537(8) Uani 1 1 d . . . H17 H 1.1699 0.6164 0.5552 0.064 Uiso 1 1 calc R . . C18 C 1.2902(4) 0.6155(3) 0.4815(3) 0.0572(9) Uani 1 1 d . . . H18 H 1.3531 0.6757 0.543 0.069 Uiso 1 1 calc R . . C19 C 1.3065(3) 0.5624(3) 0.3830(4) 0.0622(10) Uani 1 1 d . . . H19 H 1.38 0.5874 0.3778 0.075 Uiso 1 1 calc R . . C20 C 1.2138(3) 0.4719(3) 0.2916(3) 0.0479(8) Uani 1 1 d . . . H20 H 1.2249 0.4363 0.225 0.057 Uiso 1 1 calc R . . C21 C 0.9032(3) 0.2464(2) 0.2357(2) 0.0328(6) Uani 1 1 d . . . C22 C 0.9751(3) 0.2241(3) 0.3321(3) 0.0390(7) Uani 1 1 d . . . H22 H 1.0642 0.2499 0.3709 0.047 Uiso 1 1 calc R . . C23 C 0.9142(4) 0.1636(3) 0.3703(3) 0.0516(8) Uani 1 1 d . . . H23 H 0.9621 0.1482 0.4346 0.062 Uiso 1 1 calc R . . C24 C 0.7812(4) 0.1260(3) 0.3123(3) 0.0563(9) Uani 1 1 d . . . H24 H 0.7401 0.0849 0.3377 0.068 Uiso 1 1 calc R . . C25 C 0.7103(3) 0.1487(3) 0.2186(3) 0.0531(9) Uani 1 1 d . . . H25 H 0.6211 0.1235 0.1808 0.064 Uiso 1 1 calc R . . C26 C 0.7702(3) 0.2094(3) 0.1788(3) 0.0420(7) Uani 1 1 d . . . H26 H 0.7215 0.2249 0.1147 0.05 Uiso 1 1 calc R . . C27 C 0.8708(3) 0.3657(2) 0.0821(2) 0.0381(6) Uani 1 1 d . . . C28 C 0.8258(4) 0.3094(3) -0.0358(3) 0.0596(10) Uani 1 1 d . . . H28 H 0.855 0.2448 -0.0654 0.072 Uiso 1 1 calc R . . C29 C 0.7375(4) 0.3495(4) -0.1094(3) 0.0696(11) Uani 1 1 d . . . H29 H 0.7089 0.3122 -0.1886 0.083 Uiso 1 1 calc R . . C30 C 0.6915(4) 0.4424(3) -0.0685(3) 0.0615(10) Uani 1 1 d . . . H30 H 0.6337 0.4695 -0.1191 0.074 Uiso 1 1 calc R . . C31 C 0.7317(4) 0.4966(3) 0.0499(4) 0.0667(11) Uani 1 1 d . . . H31 H 0.6979 0.5584 0.0783 0.08 Uiso 1 1 calc R . . C32 C 0.8211(4) 0.4593(3) 0.1249(3) 0.0563(9) Uani 1 1 d . . . H32 H 0.8485 0.4963 0.204 0.068 Uiso 1 1 calc R . . O2A O 0.9615(9) 0.1733(6) 0.8175(6) 0.137(3) Uani 0.65 1 d PD A 1 C33A C 1.0014(15) 0.2656(8) 0.7943(9) 0.132(2) Uani 0.65 1 d PD A 1 H33A H 0.9422 0.3175 0.7944 0.158 Uiso 0.65 1 calc PR A 1 H33B H 1.0877 0.3062 0.8519 0.158 Uiso 0.65 1 calc PR A 1 C34A C 0.9995(14) 0.2161(8) 0.6841(9) 0.132(2) Uani 0.65 1 d PD A 1 H34A H 1.0862 0.2323 0.6909 0.158 Uiso 0.65 1 calc PR A 1 H34B H 0.9441 0.2497 0.6342 0.158 Uiso 0.65 1 calc PR A 1 C35A C 0.9540(14) 0.0969(8) 0.6325(10) 0.132(2) Uani 0.65 1 d PD A 1 H35A H 1.0246 0.0571 0.635 0.158 Uiso 0.65 1 calc PR A 1 H35B H 0.89 0.0728 0.5531 0.158 Uiso 0.65 1 calc PR A 1 C36A C 0.8971(15) 0.0796(11) 0.7049(8) 0.132(2) Uani 0.65 1 d PD A 1 H36A H 0.9101 0.0086 0.7129 0.158 Uiso 0.65 1 calc PR A 1 H36B H 0.8049 0.0782 0.671 0.158 Uiso 0.65 1 calc PR A 1 O2B O 0.9626(17) 0.0956(11) 0.7793(12) 0.137(3) Uani 0.35 1 d PD B 2 C33B C 1.010(3) 0.2123(13) 0.7974(17) 0.132(2) Uani 0.35 1 d PD B 2 H33C H 1.002 0.2642 0.8643 0.158 Uiso 0.35 1 calc PR B 2 H33D H 1.1007 0.2214 0.8142 0.158 Uiso 0.35 1 calc PR B 2 C34B C 0.940(2) 0.2425(15) 0.6993(16) 0.132(2) Uani 0.35 1 d PD B 2 H34C H 0.8809 0.2911 0.7123 0.158 Uiso 0.35 1 calc PR B 2 H34D H 0.9989 0.2773 0.6791 0.158 Uiso 0.35 1 calc PR B 2 C35B C 0.874(3) 0.1306(14) 0.6146(17) 0.132(2) Uani 0.35 1 d PD B 2 H35C H 0.9261 0.098 0.5752 0.158 Uiso 0.35 1 calc PR B 2 H35D H 0.7924 0.1344 0.5576 0.158 Uiso 0.35 1 calc PR B 2 C36B C 0.850(2) 0.060(2) 0.6701(16) 0.132(2) Uani 0.35 1 d PD B 2 H36C H 0.7726 0.0713 0.6813 0.158 Uiso 0.35 1 calc PR B 2 H36D H 0.8405 -0.0187 0.624 0.158 Uiso 0.35 1 calc PR B 2 O1 O 1.1618(2) -0.01722(19) 0.0227(2) 0.0542(6) Uani 1 1 d . . . F1 F 1.2453(2) 0.2067(2) 0.5644(3) 0.1028(10) Uani 1 1 d . . . F2 F 1.4062(3) 0.4529(2) 0.6692(3) 0.0945(8) Uani 1 1 d . . . F3 F 1.3552(3) 0.3401(3) 0.7446(2) 0.1055(11) Uani 1 1 d . . . F4 F 1.1958(2) 0.3771(2) 0.6082(2) 0.0826(8) Uani 1 1 d . . . F5 F 1.2962(2) 0.3242(2) 0.49354(18) 0.0752(7) Uani 1 1 d . . . F6 F 1.45270(19) 0.28184(19) 0.62896(19) 0.0637(6) Uani 1 1 d . . . P1 P 0.98454(6) 0.31694(6) 0.18123(6) 0.03035(19) Uani 1 1 d . . . P2 P 1.24755(7) 0.08625(6) 0.12055(7) 0.0376(2) Uani 1 1 d . . . P3 P 1.32378(8) 0.32942(8) 0.61879(7) 0.0481(2) 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 0.0400(15) 0.0314(16) 0.0550(18) 0.0194(13) 0.0299(14) 0.0083(13) C2 0.074(2) 0.043(2) 0.062(2) 0.0250(16) 0.0453(19) 0.0235(18) C3 0.084(3) 0.054(2) 0.083(3) 0.043(2) 0.060(2) 0.039(2) C4 0.060(2) 0.063(2) 0.078(2) 0.051(2) 0.046(2) 0.0275(19) C5 0.0514(18) 0.054(2) 0.059(2) 0.0318(17) 0.0290(16) 0.0096(17) C6 0.0471(17) 0.0376(18) 0.0565(19) 0.0223(15) 0.0286(15) 0.0117(15) C7 0.0376(15) 0.0375(17) 0.0452(16) 0.0132(13) 0.0240(13) 0.0123(13) C8 0.0434(16) 0.047(2) 0.0476(18) 0.0183(15) 0.0204(14) 0.0081(15) C9 0.0428(17) 0.045(2) 0.074(2) 0.0253(17) 0.0250(17) 0.0079(16) C10 0.061(2) 0.066(3) 0.070(2) 0.041(2) 0.043(2) 0.026(2) C11 0.071(2) 0.072(3) 0.055(2) 0.025(2) 0.037(2) 0.014(2) C12 0.062(2) 0.055(2) 0.0435(18) 0.0103(15) 0.0296(16) 0.0095(17) C13 0.0404(15) 0.0404(17) 0.0447(16) 0.0180(13) 0.0251(13) 0.0137(14) C14 0.0371(14) 0.0329(16) 0.0341(14) 0.0081(12) 0.0176(12) 0.0045(12) C15 0.0327(13) 0.0290(15) 0.0353(14) 0.0129(11) 0.0133(11) 0.0039(12) C16 0.0479(17) 0.0349(17) 0.0454(17) 0.0076(13) 0.0254(14) -0.0022(14) C17 0.062(2) 0.0386(19) 0.0459(18) 0.0026(14) 0.0226(16) -0.0066(17) C18 0.056(2) 0.040(2) 0.052(2) 0.0069(15) 0.0118(16) -0.0118(17) C19 0.0490(19) 0.053(2) 0.077(3) 0.0188(19) 0.0268(19) -0.0141(17) C20 0.0482(17) 0.0421(19) 0.0527(19) 0.0125(15) 0.0275(15) -0.0042(15) C21 0.0318(13) 0.0265(15) 0.0381(14) 0.0074(11) 0.0179(12) 0.0036(11) C22 0.0383(15) 0.0385(17) 0.0433(16) 0.0164(13) 0.0204(13) 0.0061(13) C23 0.066(2) 0.048(2) 0.058(2) 0.0267(17) 0.0384(18) 0.0128(18) C24 0.070(2) 0.042(2) 0.075(2) 0.0188(18) 0.052(2) 0.0053(18) C25 0.0381(16) 0.044(2) 0.071(2) 0.0067(16) 0.0318(17) -0.0040(15) C26 0.0338(14) 0.0367(17) 0.0476(17) 0.0076(13) 0.0179(13) 0.0034(13) C27 0.0385(15) 0.0343(17) 0.0380(15) 0.0140(12) 0.0135(12) 0.0040(13) C28 0.066(2) 0.071(3) 0.0409(18) 0.0234(17) 0.0200(17) 0.031(2) C29 0.074(3) 0.092(3) 0.0406(19) 0.034(2) 0.0157(18) 0.030(2) C30 0.055(2) 0.061(2) 0.062(2) 0.038(2) 0.0079(18) 0.0127(19) C31 0.067(2) 0.050(2) 0.071(3) 0.0271(19) 0.015(2) 0.025(2) C32 0.062(2) 0.049(2) 0.0475(18) 0.0164(16) 0.0144(16) 0.0227(18) O2A 0.265(8) 0.104(5) 0.126(5) 0.062(4) 0.147(5) 0.084(6) C33A 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) C34A 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) C35A 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) C36A 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) O2B 0.265(8) 0.104(5) 0.126(5) 0.062(4) 0.147(5) 0.084(6) C33B 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) C34B 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) C35B 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) C36B 0.209(6) 0.090(3) 0.119(4) 0.036(3) 0.098(4) -0.005(4) O1 0.0477(12) 0.0383(13) 0.0630(14) 0.0035(10) 0.0256(11) 0.0000(10) F1 0.0603(14) 0.0700(18) 0.164(3) 0.0452(18) 0.0367(17) 0.0024(14) F2 0.103(2) 0.0537(16) 0.101(2) 0.0158(14) 0.0333(16) 0.0019(15) F3 0.0984(19) 0.186(3) 0.0600(15) 0.0713(19) 0.0403(14) 0.049(2) F4 0.0832(16) 0.120(2) 0.0740(15) 0.0501(15) 0.0491(13) 0.0602(16) F5 0.0747(14) 0.109(2) 0.0472(12) 0.0348(12) 0.0263(11) 0.0363(14) F6 0.0480(11) 0.0718(15) 0.0761(14) 0.0404(12) 0.0211(10) 0.0184(11) P1 0.0294(3) 0.0285(4) 0.0312(4) 0.0094(3) 0.0134(3) 0.0040(3) P2 0.0378(4) 0.0305(4) 0.0463(4) 0.0099(3) 0.0244(3) 0.0071(3) P3 0.0492(5) 0.0546(6) 0.0376(4) 0.0187(4) 0.0150(4) 0.0157(4) #----------------------------------------------------------------------------# # 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 C1 C6 1.394(5) . ? C1 C2 1.406(4) . ? C1 P2 1.794(3) . ? C2 C3 1.373(5) . ? C3 C4 1.376(6) . ? C4 C5 1.391(5) . ? C5 C6 1.383(5) . ? C7 C8 1.377(5) . ? C7 C12 1.403(4) . ? C7 P2 1.798(3) . ? C8 C9 1.388(5) . ? C9 C10 1.382(5) . ? C10 C11 1.361(6) . ? C11 C12 1.379(5) . ? C13 C14 1.521(4) . ? C13 P2 1.815(3) . ? C14 P1 1.808(3) . ? C15 C20 1.385(4) . ? C15 C16 1.389(4) . ? C15 P1 1.795(3) . ? C16 C17 1.378(4) . ? C17 C18 1.371(5) . ? C18 C19 1.377(5) . ? C19 C20 1.386(5) . ? C21 C26 1.386(4) . ? C21 C22 1.389(4) . ? C21 P1 1.794(3) . ? C22 C23 1.381(4) . ? C23 C24 1.387(5) . ? C24 C25 1.361(5) . ? C25 C26 1.392(5) . ? C27 C28 1.383(4) . ? C27 C32 1.396(4) . ? C27 P1 1.787(3) . ? C28 C29 1.380(5) . ? C29 C30 1.357(6) . ? C30 C31 1.392(6) . ? C31 C32 1.373(5) . ? O2A C33A 1.439(8) . ? O2A C36A 1.464(8) . ? C33A C34A 1.413(8) . ? C34A C35A 1.429(8) . ? C35A C36A 1.455(9) . ? O2B C36B 1.441(10) . ? O2B C33B 1.484(10) . ? C33B C34B 1.460(18) . ? C34B C35B 1.445(10) . ? C35B C36B 1.450(10) . ? O1 P2 1.478(2) . ? F1 P3 1.561(3) . ? F2 P3 1.593(3) . ? F3 P3 1.570(2) . ? F4 P3 1.585(2) . ? F5 P3 1.594(2) . ? F6 P3 1.595(2) . ? 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 C6 C1 C2 118.8(3) . . ? C6 C1 P2 124.8(2) . . ? C2 C1 P2 116.4(3) . . ? C3 C2 C1 120.1(3) . . ? C2 C3 C4 121.0(3) . . ? C3 C4 C5 119.5(3) . . ? C6 C5 C4 120.3(3) . . ? C5 C6 C1 120.3(3) . . ? C8 C7 C12 119.1(3) . . ? C8 C7 P2 124.7(2) . . ? C12 C7 P2 116.2(3) . . ? C7 C8 C9 120.2(3) . . ? C10 C9 C8 119.6(3) . . ? C11 C10 C9 120.9(3) . . ? C10 C11 C12 119.8(3) . . ? C11 C12 C7 120.3(4) . . ? C14 C13 P2 111.89(19) . . ? C13 C14 P1 112.03(18) . . ? C20 C15 C16 119.3(3) . . ? C20 C15 P1 120.0(2) . . ? C16 C15 P1 120.8(2) . . ? C17 C16 C15 120.3(3) . . ? C18 C17 C16 120.2(3) . . ? C17 C18 C19 120.1(3) . . ? C18 C19 C20 120.2(3) . . ? C15 C20 C19 119.9(3) . . ? C26 C21 C22 120.0(3) . . ? C26 C21 P1 120.4(2) . . ? C22 C21 P1 119.5(2) . . ? C23 C22 C21 120.0(3) . . ? C22 C23 C24 119.7(3) . . ? C25 C24 C23 120.5(3) . . ? C24 C25 C26 120.6(3) . . ? C21 C26 C25 119.2(3) . . ? C28 C27 C32 119.3(3) . . ? C28 C27 P1 121.5(2) . . ? C32 C27 P1 119.0(2) . . ? C29 C28 C27 119.7(3) . . ? C30 C29 C28 121.3(4) . . ? C29 C30 C31 119.3(3) . . ? C32 C31 C30 120.3(3) . . ? C31 C32 C27 119.8(3) . . ? C33A O2A C36A 105.2(7) . . ? C34A C33A O2A 105.5(7) . . ? C33A C34A C35A 112.6(8) . . ? C34A C35A C36A 102.2(9) . . ? C35A C36A O2A 107.0(8) . . ? C36B O2B C33B 101.3(15) . . ? C34B C33B O2B 114.2(16) . . ? C35B C34B C33B 97.9(17) . . ? C34B C35B C36B 110.1(17) . . ? O2B C36B C35B 105.0(16) . . ? C27 P1 C21 109.96(14) . . ? C27 P1 C15 109.58(14) . . ? C21 P1 C15 109.18(13) . . ? C27 P1 C14 109.91(13) . . ? C21 P1 C14 109.26(13) . . ? C15 P1 C14 108.94(13) . . ? O1 P2 C1 112.22(15) . . ? O1 P2 C7 111.24(15) . . ? C1 P2 C7 107.42(14) . . ? O1 P2 C13 113.85(14) . . ? C1 P2 C13 105.50(13) . . ? C7 P2 C13 106.15(13) . . ? F1 P3 F3 92.5(2) . . ? F1 P3 F4 90.23(16) . . ? F3 P3 F4 90.80(14) . . ? F1 P3 F2 177.06(17) . . ? F3 P3 F2 89.91(19) . . ? F4 P3 F2 91.39(16) . . ? F1 P3 F5 90.15(18) . . ? F3 P3 F5 177.31(19) . . ? F4 P3 F5 89.45(12) . . ? F2 P3 F5 87.40(16) . . ? F1 P3 F6 89.97(13) . . ? F3 P3 F6 89.48(14) . . ? F4 P3 F6 179.66(14) . . ? F2 P3 F6 88.41(14) . . ? F5 P3 F6 90.27(12) . . ? #====END # Attachment 'CIF_compound_8.cif' data_BELA _database_code_depnum_ccdc_archive 'CCDC 726873' _chemical_formula_moiety 'C19 H18 P, C18 Cl12 O6 P' _chemical_formula_sum 'C37 H18 Cl12 O6 P2' _chemical_formula_weight 1045.9 _chemical_absolute_configuration rmad _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'R 3' _symmetry_space_group_name_Hall 'R 3' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -y,+x-y,+z -x+y,-x,+z 2/3+x,1/3+y,1/3+z 1/3+x,2/3+y,2/3+z 2/3-y,1/3+x-y,1/3+z 1/3-y,2/3+x-y,2/3+z 2/3-x+y,1/3-x,1/3+z 1/3-x+y,2/3-x,2/3+z _cell_length_a 17.6833(9) _cell_length_b 17.6833(9) _cell_length_c 11.4829(5) _cell_angle_alpha 90.00000 _cell_angle_beta 90.00000 _cell_angle_gamma 120.0000 _cell_volume 3109.6(3) _cell_formula_units_Z 3 _exptl_crystal_density_diffrn 1.676 _exptl_crystal_density_meas not_measured _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _cell_measurement_reflns_used 8000 _cell_measurement_theta_min 3.8 _cell_measurement_theta_max 26.8 _cell_measurement_temperature 200 _exptl_crystal_F_000 1566 _exptl_absorpt_coefficient_mu .925 _exptl_crystal_description prism _exptl_crystal_size_max .21 _exptl_crystal_size_mid .12 _exptl_crystal_size_min .11 _exptl_crystal_colour colourless _diffrn_measurement_device_type 'Stoe Ipds' _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 6 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XRED; Stoe & Cie, 1999' _exptl_absorpt_correction_T_min .8505 _exptl_absorpt_correction_T_max .9216 _diffrn_reflns_number 14385 _reflns_number_total 3003 _reflns_number_gt 2112 _reflns_threshold_expression 'refl observed if Fo > 3.99 \s(Fo)' _reflns_Friedel_coverage 1. _diffrn_reflns_theta_max 26.8 _diffrn_reflns_theta_full 26.8 _diffrn_measured_fraction_theta_max 1.0 _diffrn_measured_fraction_theta_full 1.0 _diffrn_reflns_av_R_equivalents .042 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_standards_decay_% 0 _refine_ls_structure_factor_coef F _refine_ls_R_factor_gt .024 _refine_ls_wR_factor_ref .024 _refine_ls_goodness_of_fit_ref 1.28(2) _refine_ls_number_reflns 2112 _refine_ls_number_parameters 196 _refine_ls_weighting_scheme calc _refine_ls_weighting_details \w=1/[\s^2^(Fo)+0.00015(Fo^2^)] _refine_ls_hydrogen_treatment refall _refine_ls_shift/su_max .0001 _refine_diff_density_max .308 _refine_diff_density_min -.291 _refine_ls_extinction_method none _refine_ls_abs_structure_details Flack_xabs_refined _refine_ls_abs_structure_Flack .00(9) _computing_data_collection 'EXPOSE (Stoe & Cie, 1999)' _computing_cell_refinement 'CELL (Stoe & Cie, 1999)' _computing_data_reduction 'XRED (Stoe & Cie, 1999)' _computing_structure_solution SIR97 _computing_structure_refinement xtal_CRYLSQ _computing_molecular_graphics xtal_gx3 _computing_publication_material xtal_CIFIO loop_ _atom_type_symbol _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .002 .002 H Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 0 0 O Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .008 .006 P Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .09 .095 Cl Int._Tables_Vol_IV_Tables_2.2B_and_2.3.1 .132 .159 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type P1 .00000 .00000 .50000 .0268(7) 1.00000 Uani Cl1 .23252(9) .22482(9) .27915(16) .0381(6) 1.00000 Uani Cl2 .29411(11) .40549(10) .40199(16) .0586(8) 1.00000 Uani Cl3 .19925(12) .41239(10) .62927(18) .0593(9) 1.00000 Uani Cl4 .04055(11) .24037(10) .72837(16) .0477(8) 1.00000 Uani O1 .0811(3) .0749(3) .4107(4) .0280(17) 1.00000 Uani O2 .0084(3) .0818(3) .5881(4) .0299(18) 1.00000 Uani C1 .1145(3) .1567(3) .4523(4) .026(3) 1.00000 Uani C2 .1826(3) .2315(4) .4046(5) .029(3) 1.00000 Uani C3 .2082(4) .3109(4) .4597(5) .036(3) 1.00000 Uani C4 .1657(4) .3144(4) .5590(5) .037(3) 1.00000 Uani C5 .0967(4) .2391(4) .6056(4) .030(3) 1.00000 Uani C6 .0725(3) .1605(3) .5528(4) .025(3) 1.00000 Uani P1a .00000 .00000 .0171(3) .0303(10) 1.00000 Uani C1a .0323(4) .1079(4) .0692(5) .030(3) 1.00000 Uani C2a .0898(4) .1817(4) .0058(6) .042(3) 1.00000 Uani C3a .1106(5) .2630(5) .0461(8) .053(4) 1.00000 Uani C4a .0777(4) .2732(4) .1476(7) .052(4) 1.00000 Uani C5a .0211(4) .2002(4) .2130(6) .042(3) 1.00000 Uani C6a -.0016(4) .1181(4) .1731(5) .029(3) 1.00000 Uani C7a .00000 .00000 -.1391(9) .054(5) 1.00000 Uani H2a .108(4) .175(3) -.061(5) .031(14) 1.00000 Uiso H3a .148(5) .306(5) -.001(6) .07(3) 1.00000 Uiso H4a .099(4) .331(4) .181(5) .028(14) 1.00000 Uiso H5a -.001(4) .208(4) .279(5) .031(14) 1.00000 Uiso H6a -.038(3) .066(4) .218(4) .025(12) 1.00000 Uiso H7a -.031(4) .024(4) -.166(5) .048(16) 1.00000 Uiso loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 P1 .0288(6) .0288(6) .0230(9) .0144(3) .00000 .00000 Cl1 .0313(7) .0437(8) .0350(7) .0154(7) .0086(6) -.0001(7) Cl2 .0592(10) .0315(8) .0584(10) .0026(7) .0169(8) .0001(7) Cl3 .0823(13) .0312(8) .0536(10) .0204(8) .0097(9) -.0113(7) Cl4 .0717(11) .0452(9) .0322(8) .0337(8) .0135(8) -.0036(7) O1 .029(2) .0265(19) .025(2) .0113(17) .0038(15) -.0038(15) O2 .035(2) .029(3) .026(3) .0165(17) .0045(17) .0006(16) C1 .023(3) .028(3) .027(3) .013(3) -.003(2) -.004(3) C2 .028(3) .037(3) .024(3) .017(3) -.001(3) .000(3) C3 .035(3) .031(3) .034(3) .011(3) -.004(3) -.001(3) C4 .050(4) .030(3) .035(3) .023(3) -.006(3) -.004(3) C5 .039(3) .034(3) .024(3) .023(3) -.000(3) -.001(3) C6 .029(3) .029(3) .021(3) .017(3) -.001(2) .001(2) P1a .0346(7) .0346(7) .0217(14) .0173(4) .00000 .00000 C1a .028(3) .035(3) .030(3) .017(3) -.001(2) .006(3) C2a .038(4) .046(4) .042(4) .021(3) .012(3) .010(3) C3a .043(4) .034(4) .074(5) .013(4) .012(4) .021(4) C4a .047(4) .032(4) .079(5) .021(3) -.010(4) -.005(4) C5a .046(4) .046(4) .041(4) .029(3) -.005(3) -.004(3) C6a .027(3) .033(3) .027(3) .015(3) .000(3) .002(3) C7a .068(5) .068(5) .027(6) .034(3) .00000 .00000 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance P1 O1 . . 1.721(4) P1 O2 . . 1.709(5) P1 O1 . 2 1.721(6) P1 O2 . 2 1.709(4) P1 O1 . 3 1.721(5) P1 O2 . 3 1.709(7) Cl1 C2 . . 1.724(6) Cl2 C3 . . 1.733(5) Cl3 C4 . . 1.726(6) Cl4 C5 . . 1.730(6) O1 C1 . . 1.346(6) O2 C6 . . 1.345(5) C1 C2 . . 1.380(6) C1 C6 . . 1.393(7) C2 C3 . . 1.393(8) C3 C4 . . 1.385(9) C4 C5 . . 1.387(6) C5 C6 . . 1.374(8) P1a C1a . . 1.799(6) P1a C7a . . 1.794(11) P1a C1a . 2 1.799(5) P1a C1a . 3 1.799(11) C1a C2a . . 1.393(7) C1a C6a . . 1.385(8) C2a C3a . . 1.374(10) C2a H2a . . .86(6) C3a C4a . . 1.355(12) C3a H3a . . .91(7) C4a C5a . . 1.393(8) C4a H4a . . .98(6) C5a C6a . . 1.378(9) C5a H5a . . .89(6) C6a H6a . . .97(5) C7a H7a . . .90(8) C7a H7a . 2 .90(11) C7a H7a . 3 .90(10) loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle O1 P1 O2 . . . 90.83(17) O1 P1 O1 . . 2 88.18(19) O1 P1 O2 . . 2 178.8(4) O1 P1 O1 . . 3 88.2(2) O1 P1 O2 . . 3 92.5(3) O2 P1 O1 . . 2 92.5(3) O2 P1 O2 . . 2 88.5(3) O2 P1 O1 . . 3 178.8(3) O2 P1 O2 . . 3 88.5(3) O1 P1 O2 2 . 2 90.8(3) O1 P1 O1 2 . 3 88.2(4) O1 P1 O2 2 . 3 178.8(3) O2 P1 O1 2 . 3 92.5(3) O2 P1 O2 2 . 3 88.5(3) O1 P1 O2 3 . 3 90.8(3) P1 O1 C1 . . . 111.4(4) P1 O2 C6 . . . 111.7(4) O1 C1 C2 . . . 126.3(5) O1 C1 C6 . . . 112.8(4) C2 C1 C6 . . . 120.9(5) Cl1 C2 C1 . . . 119.8(4) Cl1 C2 C3 . . . 121.9(4) C1 C2 C3 . . . 118.3(5) Cl2 C3 C2 . . . 119.1(5) Cl2 C3 C4 . . . 120.3(5) C2 C3 C4 . . . 120.6(5) Cl3 C4 C3 . . . 120.6(4) Cl3 C4 C5 . . . 118.6(5) C3 C4 C5 . . . 120.8(5) Cl4 C5 C4 . . . 122.5(5) Cl4 C5 C6 . . . 118.8(4) C4 C5 C6 . . . 118.7(5) O2 C6 C1 . . . 113.2(5) O2 C6 C5 . . . 126.1(5) C1 C6 C5 . . . 120.7(4) C1a P1a C7a . . . 109.42(18) C1a P1a C1a . . 2 109.5(4) C1a P1a C1a . . 3 109.5(3) C7a P1a C1a . . 2 109.42(18) C7a P1a C1a . . 3 109.4(3) C1a P1a C1a 2 . 3 109.5(4) P1a C1a C2a . . . 121.0(5) P1a C1a C6a . . . 119.7(4) C2a C1a C6a . . . 119.4(6) C1a C2a C3a . . . 119.4(7) C1a C2a H2a . . . 119(3) C3a C2a H2a . . . 122(4) C2a C3a C4a . . . 121.5(6) C2a C3a H3a . . . 112(6) C4a C3a H3a . . . 126(6) C3a C4a C5a . . . 119.8(7) C3a C4a H4a . . . 121(3) C5a C4a H4a . . . 119(3) C4a C5a C6a . . . 119.6(6) C4a C5a H5a . . . 119(4) C6a C5a H5a . . . 122(4) C1a C6a C5a . . . 120.4(5) C1a C6a H6a . . . 118(4) C5a C6a H6a . . . 122(4) P1a C7a H7a . . . 110(4) P1a C7a H7a . . 2 110(5) P1a C7a H7a . . 3 110(4) H7a C7a H7a . . 2 109(7) H7a C7a H7a . . 3 109(7) H7a C7a H7a 2 . 3 109(7) 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion O2 P1 O1 C1 . . . . 3.3(4) O1 P1 O1 C1 2 . . . 95.7(5) O1 P1 O1 C1 3 . . . -176.0(5) O2 P1 O1 C1 3 . . . -85.3(4) O1 P1 O2 C6 . . . . -2.8(4) O1 P1 O2 C6 2 . . . -91.0(4) O2 P1 O2 C6 2 . . . 178.2(5) O2 P1 O2 C6 3 . . . 89.7(4) P1 O1 C1 C2 . . . . 177.2(5) P1 O1 C1 C6 . . . . -3.0(6) P1 O2 C6 C1 . . . . 1.6(6) P1 O2 C6 C5 . . . . -179.1(5) O1 C1 C2 Cl1 . . . . .5(9) O1 C1 C2 C3 . . . . 179.8(6) C6 C1 C2 Cl1 . . . . -179.3(5) C6 C1 C2 C3 . . . . .1(9) O1 C1 C6 O2 . . . . .9(7) O1 C1 C6 C5 . . . . -178.4(6) C2 C1 C6 O2 . . . . -179.3(6) C2 C1 C6 C5 . . . . 1.3(9) Cl1 C2 C3 Cl2 . . . . -1.2(8) Cl1 C2 C3 C4 . . . . 178.6(6) C1 C2 C3 Cl2 . . . . 179.5(5) C1 C2 C3 C4 . . . . -.7(10) Cl2 C3 C4 Cl3 . . . . -1.9(9) Cl2 C3 C4 C5 . . . . 179.8(6) C2 C3 C4 Cl3 . . . . 178.4(5) C2 C3 C4 C5 . . . . .0(10) Cl3 C4 C5 Cl4 . . . . 2.5(8) Cl3 C4 C5 C6 . . . . -177.0(5) C3 C4 C5 Cl4 . . . . -179.2(6) C3 C4 C5 C6 . . . . 1.4(10) Cl4 C5 C6 O2 . . . . -.8(9) Cl4 C5 C6 C1 . . . . 178.5(5) C4 C5 C6 O2 . . . . 178.7(6) C4 C5 C6 C1 . . . . -2.0(9) C7a P1a C1a C2a . . . . -30.9(6) C7a P1a C1a C6a . . . . 148.1(5) C1a P1a C1a C2a 2 . . . -150.8(6) C1a P1a C1a C6a 2 . . . 28.2(6) C1a P1a C1a C2a 3 . . . 89.1(6) C1a P1a C1a C6a 3 . . . -91.9(6) C1a P1a C7a H7a . . . . -51(3) C1a P1a C7a H7a 2 . . . 69(3) C1a P1a C7a H7a 3 . . . -171(3) P1a C1a C2a C3a . . . . 177.7(6) P1a C1a C2a H2a . . . . 3(5) C6a C1a C2a C3a . . . . -1.4(10) C6a C1a C2a H2a . . . . -176(5) P1a C1a C6a C5a . . . . -178.7(5) P1a C1a C6a H6a . . . . 5(4) C2a C1a C6a C5a . . . . .4(9) C2a C1a C6a H6a . . . . -176(4) C1a C2a C3a C4a . . . . 1.4(12) C1a C2a C3a H3a . . . . -180(6) H2a C2a C3a C4a . . . . 176(5) H2a C2a C3a H3a . . . . -5(8) C2a C3a C4a C5a . . . . -.4(12) C2a C3a C4a H4a . . . . 172(5) H3a C3a C4a C5a . . . . -179(7) H3a C3a C4a H4a . . . . -7(8) C3a C4a C5a C6a . . . . -.6(11) C3a C4a C5a H5a . . . . -178(5) H4a C4a C5a C6a . . . . -173(5) H4a C4a C5a H5a . . . . 9(7) C4a C5a C6a C1a . . . . .6(10) C4a C5a C6a H6a . . . . 177(4) H5a C5a C6a C1a . . . . 178(5) H5a C5a C6a H6a . . . . -6(7) #=END=======================================================