# ic001295k.cif # TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and reactions of the fluorinated cyclic thionylphosphazene NSO(Ar)[NPF2]2 (Ar = 4-ButC6H4) with difunctional reagents. IC001295K ; loop_ _publ_author_name _publ_author_address 'Anil J. Elias' ; Department of Chemistry, University of Idaho, Moscow, ID, 83844-2343, U.S.A. ; 'Brendan Twamley' ; Department of Chemistry, University of Idaho, Moscow, ID, 83844-2343, U.S.A. ; 'Jean'ne Shreeve*' ; Department of Chemistry, University of Idaho, Moscow, ID, 83844-2343, U.S.A. ; data_bt174 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'para-t-butylphenylthiaphospahzene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H13 F4 N3 O P2 S' _chemical_formula_weight 361.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.0392(15) _cell_length_b 9.9467(18) _cell_length_c 10.4353(19) _cell_angle_alpha 66.655(3) _cell_angle_beta 88.870(3) _cell_angle_gamma 83.702(3) _cell_volume 761.3(2) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 929 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 26.68 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.576 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.466 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8540 _exptl_absorpt_correction_T_max 0.9419 _exptl_absorpt_process_details 'SADABS (Sheldrick 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART 1000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number '50 frames remeasured' _diffrn_standards_interval_count 'beginning and end' _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 0.01' _diffrn_reflns_number 7650 _diffrn_reflns_av_R_equivalents 0.0313 _diffrn_reflns_av_sigmaI/netI 0.0466 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2674 _reflns_number_gt 1786 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL v. 5.10' _computing_structure_solution 'XS, Bruker SHELXTL v. 5.10' _computing_structure_refinement 'XL, Bruker SHELXTL v. 5.10' _computing_molecular_graphics 'XP, Bruker SHELXTL v. 5.10' _computing_publication_material 'XCIF, Bruker SHELXTL v. 5.10' _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. The oxygen site was disordered and the occupancy refined as 80% and 20%. Some carbon atoms show large librational movement around the organic axis. Attempts at refining a complete disordered carbon backbone or a disordered tBu group were unsatisfactory and led to unstable refinements. The model shown gave the best refinement in spite of the large libration of several carbon atoms. ; _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^)+(0.0557P)^2^+1.8153P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2674 _refine_ls_number_parameters 200 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1078 _refine_ls_R_factor_gt 0.0687 _refine_ls_wR_factor_ref 0.1693 _refine_ls_wR_factor_gt 0.1495 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.3482(2) 0.2393(2) 0.46789(18) 0.0713(5) Uani 1 1 d . . . P2 P 0.59764(18) 0.16955(18) 0.65387(19) 0.0664(5) Uani 1 1 d . . . N1 N 0.5139(6) 0.1473(5) 0.5335(6) 0.0707(14) Uani 1 1 d . . . N2 N 0.5111(5) 0.2842(6) 0.7080(5) 0.0650(13) Uani 1 1 d . A . N3 N 0.2733(6) 0.3592(5) 0.5205(4) 0.0652(13) Uani 1 1 d . A . F1 F 0.3615(6) 0.3069(6) 0.3111(4) 0.1278(18) Uani 1 1 d . . . F2 F 0.2168(5) 0.1347(6) 0.4765(5) 0.1179(16) Uani 1 1 d . . . F3 F 0.7798(4) 0.1947(5) 0.6219(5) 0.1000(14) Uani 1 1 d . . . F4 F 0.6309(6) 0.0237(5) 0.7792(5) 0.141(2) Uani 1 1 d . . . S1 S 0.34774(18) 0.38639(14) 0.64354(15) 0.0569(4) Uani 1 1 d . . . C1 C 0.1978(6) 0.3374(5) 0.7752(5) 0.0400(11) Uani 1 1 d . A . C2 C 0.2459(7) 0.2704(8) 0.9110(6) 0.079(2) Uani 1 1 d . . . H2A H 0.3600 0.2429 0.9364 0.095 Uiso 1 1 calc R A . C3 C 0.1262(7) 0.2424(8) 1.0131(6) 0.087(2) Uani 1 1 d . A . H3A H 0.1616 0.1970 1.1074 0.104 Uiso 1 1 calc R . . C4 C -0.0409(5) 0.2784(5) 0.9819(5) 0.0364(10) Uani 1 1 d . . . C5 C -0.0844(6) 0.3434(7) 0.8438(5) 0.0613(15) Uani 1 1 d . A . H5A H -0.1986 0.3681 0.8180 0.074 Uiso 1 1 calc R . . C6 C 0.0322(7) 0.3748(7) 0.7398(6) 0.0685(17) Uani 1 1 d . . . H6A H -0.0026 0.4217 0.6455 0.082 Uiso 1 1 calc R A . C7 C -0.1716(6) 0.2437(5) 1.0957(5) 0.0485(12) Uani 1 1 d . A . C8 C -0.1031(8) 0.2403(9) 1.2305(7) 0.092(2) Uani 1 1 d . . . H8A H -0.0827 0.3389 1.2182 0.138 Uiso 1 1 calc R A . H8B H 0.0010 0.1756 1.2565 0.138 Uiso 1 1 calc R . . H8C H -0.1835 0.2041 1.3034 0.138 Uiso 1 1 calc R . . C9 C -0.2288(10) 0.0956(9) 1.1215(8) 0.111(3) Uani 1 1 d . . . H9A H -0.1319 0.0239 1.1340 0.167 Uiso 1 1 calc R A . H9B H -0.2962 0.1037 1.0423 0.167 Uiso 1 1 calc R . . H9C H -0.2949 0.0643 1.2050 0.167 Uiso 1 1 calc R . . C10 C -0.3236(10) 0.3607(11) 1.0489(8) 0.142(4) Uani 1 1 d . . . H10A H -0.2871 0.4576 1.0232 0.213 Uiso 1 1 calc R A . H10B H -0.4012 0.3424 1.1248 0.213 Uiso 1 1 calc R . . H10C H -0.3788 0.3563 0.9690 0.213 Uiso 1 1 calc R . . O1A O 0.430(11) 0.510(7) 0.652(7) 0.048(16) Uani 0.20(8) 1 d P A 1 O1B O 0.351(5) 0.5426(15) 0.594(4) 0.085(8) Uani 0.80(8) 1 d P A 2 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 0.0592(10) 0.1023(13) 0.0668(11) -0.0503(10) 0.0115(8) -0.0051(9) P2 0.0414(8) 0.0689(10) 0.0879(12) -0.0316(9) 0.0121(7) -0.0013(7) N1 0.055(3) 0.064(3) 0.117(4) -0.062(3) 0.014(3) -0.008(2) N2 0.041(2) 0.102(4) 0.073(3) -0.054(3) 0.016(2) -0.018(2) N3 0.065(3) 0.071(3) 0.040(3) -0.010(2) 0.011(2) 0.019(2) F1 0.114(3) 0.211(5) 0.062(3) -0.066(3) 0.021(2) 0.011(3) F2 0.072(3) 0.192(5) 0.141(4) -0.114(4) 0.008(2) -0.040(3) F3 0.0412(19) 0.155(4) 0.135(3) -0.090(3) 0.022(2) -0.011(2) F4 0.093(3) 0.112(3) 0.140(4) 0.018(3) 0.009(3) 0.046(3) S1 0.0675(9) 0.0412(7) 0.0676(9) -0.0266(7) 0.0385(7) -0.0166(6) C1 0.045(3) 0.032(2) 0.045(3) -0.017(2) 0.013(2) -0.007(2) C2 0.032(3) 0.122(5) 0.059(4) -0.015(4) 0.008(3) 0.012(3) C3 0.049(3) 0.132(6) 0.038(3) 0.000(3) 0.001(3) 0.029(4) C4 0.038(2) 0.031(2) 0.041(3) -0.017(2) 0.006(2) -0.0019(19) C5 0.034(3) 0.108(5) 0.045(3) -0.033(3) 0.001(2) -0.008(3) C6 0.049(3) 0.112(5) 0.034(3) -0.020(3) 0.005(2) -0.001(3) C7 0.046(3) 0.052(3) 0.045(3) -0.018(2) 0.013(2) -0.004(2) C8 0.082(5) 0.159(7) 0.067(4) -0.073(5) 0.030(3) -0.038(5) C9 0.132(7) 0.123(6) 0.109(6) -0.062(5) 0.077(5) -0.088(6) C10 0.096(6) 0.187(9) 0.075(5) -0.003(5) 0.042(4) 0.073(6) O1A 0.06(3) 0.041(18) 0.05(2) -0.024(16) 0.030(19) -0.026(16) O1B 0.104(14) 0.045(4) 0.110(14) -0.035(6) 0.068(13) -0.022(6) _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 F1 1.510(4) . ? P1 N1 1.534(5) . ? P1 F2 1.540(4) . ? P1 N3 1.561(5) . ? P1 P2 2.655(2) . ? P2 F4 1.520(4) . ? P2 F3 1.521(4) . ? P2 N1 1.539(5) . ? P2 N2 1.557(5) . ? N2 S1 1.553(5) . ? N3 S1 1.555(5) . ? S1 O1B 1.434(9) . ? S1 O1A 1.49(3) . ? S1 C1 1.764(4) . ? C1 C2 1.349(7) . ? C1 C6 1.360(7) . ? C2 C3 1.386(8) . ? C3 C4 1.363(7) . ? C4 C5 1.359(7) . ? C4 C7 1.530(6) . ? C5 C6 1.382(7) . ? C7 C8 1.507(7) . ? C7 C9 1.511(8) . ? C7 C10 1.532(8) . ? 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 F1 P1 N1 109.5(3) . . ? F1 P1 F2 97.8(3) . . ? N1 P1 F2 108.9(3) . . ? F1 P1 N3 109.8(3) . . ? N1 P1 N3 118.8(3) . . ? F2 P1 N3 110.0(3) . . ? F1 P1 P2 126.5(2) . . ? N1 P1 P2 30.26(17) . . ? F2 P1 P2 123.1(2) . . ? N3 P1 P2 88.55(19) . . ? F4 P2 F3 96.9(3) . . ? F4 P2 N1 110.5(3) . . ? F3 P2 N1 110.1(3) . . ? F4 P2 N2 107.3(3) . . ? F3 P2 N2 110.6(2) . . ? N1 P2 N2 119.2(3) . . ? F4 P2 P1 125.2(2) . . ? F3 P2 P1 126.2(2) . . ? N1 P2 P1 30.16(17) . . ? N2 P2 P1 89.07(18) . . ? P1 N1 P2 119.6(3) . . ? S1 N2 P2 124.5(3) . . ? S1 N3 P1 124.8(3) . . ? O1B S1 O1A 33(2) . . ? O1B S1 N2 118.4(18) . . ? O1A S1 N2 88(4) . . ? O1B S1 N3 105.8(19) . . ? O1A S1 N3 133(3) . . ? N2 S1 N3 113.0(2) . . ? O1B S1 C1 107.3(3) . . ? O1A S1 C1 107.8(11) . . ? N2 S1 C1 106.2(2) . . ? N3 S1 C1 105.4(2) . . ? C2 C1 C6 119.6(4) . . ? C2 C1 S1 120.7(4) . . ? C6 C1 S1 119.6(4) . . ? C1 C2 C3 119.7(5) . . ? C4 C3 C2 122.4(5) . . ? C5 C4 C3 116.1(4) . . ? C5 C4 C7 122.1(4) . . ? C3 C4 C7 121.8(4) . . ? C4 C5 C6 122.7(5) . . ? C1 C6 C5 119.4(5) . . ? C8 C7 C9 109.1(5) . . ? C8 C7 C4 112.0(4) . . ? C9 C7 C4 109.0(4) . . ? C8 C7 C10 107.9(6) . . ? C9 C7 C10 108.6(6) . . ? C4 C7 C10 110.2(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.526 _refine_diff_density_min -0.466 _refine_diff_density_rms 0.066 #===END data_bt196 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ansa-thionylphosphazene' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H19 F2 N3 O3 P2 S' _chemical_formula_weight 397.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.5112(10) _cell_length_b 10.1847(12) _cell_length_c 11.3687(13) _cell_angle_alpha 111.302(2) _cell_angle_beta 98.453(2) _cell_angle_gamma 101.392(2) _cell_volume 873.87(18) _cell_formula_units_Z 2 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 998 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 28.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.510 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.406 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.8107 _exptl_absorpt_correction_T_max 0.8811 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART 1000' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number '100 frames remeasured' _diffrn_standards_interval_count 'beginning and end' _diffrn_standards_interval_time ? _diffrn_standards_decay_% '< 0.1' _diffrn_reflns_number 9631 _diffrn_reflns_av_R_equivalents 0.0229 _diffrn_reflns_av_sigmaI/netI 0.0241 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3060 _reflns_number_gt 2419 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL v. 5.10' _computing_structure_solution 'XS, Bruker SHELXTL v. 5.10' _computing_structure_refinement 'XL, Bruker SHELXTL v. 5.10' _computing_molecular_graphics 'XP, Bruker SHELXTL v. 5.10' _computing_publication_material 'XCIF, Bruker SHELXTL v. 5.10' _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. The thionyl oxygen and the fluorine atoms sites were disordered and the site occupancy modelled as 53% O1a, and 57% F1a F2a. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+1.3478P] 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 3060 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0710 _refine_ls_R_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.1336 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 S1 S 0.28413(15) 0.61433(10) 0.17864(11) 0.0652(3) Uani 1 1 d . . . P1 P 0.24700(14) 0.77821(18) 0.03774(11) 0.0779(4) Uani 1 1 d . . . P2 P 0.50379(13) 0.87474(12) 0.23678(10) 0.0644(3) Uani 1 1 d . A . N1 N 0.2009(4) 0.6304(4) 0.0555(3) 0.0803(12) Uani 1 1 d . A . N2 N 0.3736(4) 0.9096(4) 0.1551(4) 0.0661(9) Uani 1 1 d . A . N3 N 0.4570(4) 0.7233(4) 0.2450(3) 0.0656(9) Uani 1 1 d . A . F1A F 0.1061(10) 0.8625(18) 0.0264(9) 0.071(3) Uani 0.57(3) 1 d P A 1 F2A F 0.5630(11) 0.9719(17) 0.3827(7) 0.077(3) Uani 0.57(3) 1 d P A 1 O1A O 0.250(2) 0.4563(7) 0.1177(18) 0.063(4) Uani 0.53(3) 1 d P B 1 F1B F 0.0656(15) 0.758(4) -0.0178(16) 0.093(7) Uani 0.43(3) 1 d P A 2 F2B F 0.527(2) 1.0263(15) 0.354(2) 0.093(5) Uani 0.43(3) 1 d P A 2 O1B O 0.346(3) 0.4867(16) 0.187(2) 0.071(6) Uani 0.47(3) 1 d P B 2 O2 O 0.2970(4) 0.7525(5) -0.0933(3) 0.1100(14) Uani 1 1 d . A . O3 O 0.6737(3) 0.9008(4) 0.2020(3) 0.0939(11) Uani 1 1 d . . . C1 C 0.1599(4) 0.6555(3) 0.2913(3) 0.0431(8) Uani 1 1 d . B . C2 C 0.2294(5) 0.6961(4) 0.4204(4) 0.0574(10) Uani 1 1 d . . . H2B H 0.3417 0.7035 0.4478 0.069 Uiso 1 1 calc R B . C3 C 0.1336(4) 0.7262(4) 0.5101(3) 0.0534(9) Uani 1 1 d . B . H3B H 0.1824 0.7538 0.5983 0.064 Uiso 1 1 calc R . . C4 C -0.0311(4) 0.7166(3) 0.4735(3) 0.0379(7) Uani 1 1 d . . . C5 C -0.0976(4) 0.6750(4) 0.3426(3) 0.0520(9) Uani 1 1 d . B . H5A H -0.2098 0.6677 0.3147 0.062 Uiso 1 1 calc R . . C6 C -0.0038(5) 0.6437(4) 0.2513(3) 0.0536(9) Uani 1 1 d . . . H6A H -0.0522 0.6147 0.1627 0.064 Uiso 1 1 calc R B . C7 C -0.1342(4) 0.7588(4) 0.5735(3) 0.0477(8) Uani 1 1 d . B . C8 C -0.3065(5) 0.6532(5) 0.5238(4) 0.0753(13) Uani 1 1 d . . . H8A H -0.3594 0.6527 0.4419 0.113 Uiso 1 1 calc R B . H8B H -0.3714 0.6842 0.5869 0.113 Uiso 1 1 calc R . . H8C H -0.2985 0.5554 0.5107 0.113 Uiso 1 1 calc R . . C9 C -0.0550(5) 0.7572(6) 0.7018(4) 0.0822(15) Uani 1 1 d . . . H9A H -0.0488 0.6588 0.6881 0.123 Uiso 1 1 calc R B . H9B H -0.1210 0.7882 0.7641 0.123 Uiso 1 1 calc R . . H9C H 0.0554 0.8236 0.7351 0.123 Uiso 1 1 calc R . . C10 C -0.1460(7) 0.9136(5) 0.5958(5) 0.0950(17) Uani 1 1 d . . . H10A H -0.1950 0.9151 0.5138 0.142 Uiso 1 1 calc R B . H10B H -0.0364 0.9812 0.6309 0.142 Uiso 1 1 calc R . . H10C H -0.2142 0.9426 0.6567 0.142 Uiso 1 1 calc R . . C11 C 0.4411(6) 0.6971(6) -0.1152(4) 0.0834(14) Uani 1 1 d . . . H11A H 0.4372 0.6608 -0.2084 0.100 Uiso 1 1 calc R A . H11B H 0.4336 0.6138 -0.0904 0.100 Uiso 1 1 calc R . . C12 C 0.6042(5) 0.8072(4) -0.0422(4) 0.0653(11) Uani 1 1 d . A . H12A H 0.5869 0.9049 -0.0184 0.078 Uiso 1 1 calc R . . H12B H 0.6773 0.7975 -0.1022 0.078 Uiso 1 1 calc R . . C13 C 0.6946(5) 0.8007(5) 0.0794(4) 0.0695(12) Uani 1 1 d . A . H13B H 0.6576 0.7005 0.0734 0.083 Uiso 1 1 calc R . . H13A H 0.8126 0.8209 0.0816 0.083 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0976(8) 0.0431(5) 0.0795(7) 0.0281(5) 0.0682(6) 0.0310(5) P1 0.0538(6) 0.1551(13) 0.0653(7) 0.0708(8) 0.0354(5) 0.0494(7) P2 0.0471(6) 0.0658(7) 0.0582(6) 0.0015(5) 0.0278(5) 0.0018(5) N1 0.074(2) 0.094(3) 0.0357(17) 0.0040(17) 0.0241(16) -0.0230(19) N2 0.079(2) 0.057(2) 0.088(2) 0.0372(18) 0.050(2) 0.0347(18) N3 0.0502(18) 0.108(3) 0.074(2) 0.059(2) 0.0366(16) 0.0392(19) F1A 0.062(3) 0.102(8) 0.073(4) 0.044(5) 0.030(3) 0.048(4) F2A 0.064(4) 0.082(6) 0.052(3) -0.002(3) 0.012(2) 0.006(3) O1A 0.083(8) 0.041(3) 0.080(8) 0.023(4) 0.052(7) 0.031(4) F1B 0.063(5) 0.18(2) 0.078(7) 0.079(10) 0.034(5) 0.069(8) F2B 0.076(7) 0.060(6) 0.100(9) -0.017(5) 0.048(6) 0.004(4) O1B 0.104(12) 0.061(5) 0.089(10) 0.043(6) 0.065(10) 0.055(7) O2 0.072(2) 0.236(5) 0.074(2) 0.098(3) 0.0438(17) 0.067(3) O3 0.0514(17) 0.106(2) 0.085(2) 0.0020(18) 0.0390(16) -0.0088(16) C1 0.058(2) 0.0329(16) 0.0477(19) 0.0177(14) 0.0316(16) 0.0164(15) C2 0.045(2) 0.078(3) 0.057(2) 0.026(2) 0.0245(17) 0.0267(19) C3 0.045(2) 0.079(3) 0.0402(18) 0.0235(18) 0.0181(15) 0.0209(18) C4 0.0397(17) 0.0369(16) 0.0403(17) 0.0165(14) 0.0160(14) 0.0109(13) C5 0.044(2) 0.067(2) 0.0439(19) 0.0184(17) 0.0153(15) 0.0186(17) C6 0.060(2) 0.062(2) 0.0368(18) 0.0158(16) 0.0188(16) 0.0171(18) C7 0.0424(19) 0.062(2) 0.0429(18) 0.0212(16) 0.0211(15) 0.0166(16) C8 0.041(2) 0.116(4) 0.068(3) 0.038(3) 0.0237(19) 0.010(2) C9 0.057(3) 0.146(5) 0.048(2) 0.044(3) 0.0248(19) 0.018(3) C10 0.125(4) 0.083(3) 0.103(4) 0.031(3) 0.081(3) 0.058(3) C11 0.076(3) 0.127(4) 0.058(3) 0.038(3) 0.041(2) 0.033(3) C12 0.077(3) 0.065(2) 0.094(3) 0.051(2) 0.063(3) 0.039(2) C13 0.057(2) 0.082(3) 0.082(3) 0.033(2) 0.044(2) 0.028(2) _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 S1 O1A 1.450(6) . ? S1 O1B 1.522(10) . ? S1 N3 1.544(4) . ? S1 N1 1.552(4) . ? S1 C1 1.766(3) . ? P1 F1B 1.522(9) . ? P1 O2 1.555(3) . ? P1 N2 1.562(4) . ? P1 N1 1.572(4) . ? P1 F1A 1.623(7) . ? P1 P2 2.6353(17) . ? P2 N2 1.520(4) . ? P2 F2A 1.533(8) . ? P2 O3 1.553(3) . ? P2 N3 1.556(4) . ? P2 F2B 1.585(9) . ? O2 C11 1.464(5) . ? O3 C13 1.458(5) . ? C1 C6 1.368(5) . ? C1 C2 1.371(5) . ? C2 C3 1.383(5) . ? C3 C4 1.376(5) . ? C4 C5 1.384(4) . ? C4 C7 1.528(4) . ? C5 C6 1.386(5) . ? C7 C9 1.521(5) . ? C7 C8 1.523(5) . ? C7 C10 1.530(6) . ? C11 C12 1.498(6) . ? C12 C13 1.511(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1A S1 O1B 37.4(3) . . ? O1A S1 N3 125.5(8) . . ? O1B S1 N3 92.4(11) . . ? O1A S1 N1 95.4(9) . . ? O1B S1 N1 128.2(9) . . ? N3 S1 N1 112.27(17) . . ? O1A S1 C1 107.5(3) . . ? O1B S1 C1 107.2(3) . . ? N3 S1 C1 107.14(17) . . ? N1 S1 C1 107.63(19) . . ? F1B P1 O2 94.8(4) . . ? F1B P1 N2 129.8(12) . . ? O2 P1 N2 112.6(2) . . ? F1B P1 N1 90.0(11) . . ? O2 P1 N1 110.6(2) . . ? N2 P1 N1 115.75(18) . . ? F1B P1 F1A 35.5(8) . . ? O2 P1 F1A 101.0(3) . . ? N2 P1 F1A 96.3(5) . . ? N1 P1 F1A 119.2(5) . . ? F1B P1 P2 150.9(7) . . ? O2 P1 P2 112.74(13) . . ? N2 P1 P2 30.76(12) . . ? N1 P1 P2 88.95(14) . . ? F1A P1 P2 124.6(5) . . ? N2 P2 F2A 118.4(6) . . ? N2 P2 O3 112.7(2) . . ? F2A P2 O3 97.6(3) . . ? N2 P2 N3 117.02(18) . . ? F2A P2 N3 98.5(6) . . ? O3 P2 N3 110.22(19) . . ? N2 P2 F2B 89.9(11) . . ? F2A P2 F2B 30.4(6) . . ? O3 P2 F2B 100.9(4) . . ? N3 P2 F2B 124.0(9) . . ? N2 P2 P1 31.72(13) . . ? F2A P2 P1 142.3(5) . . ? O3 P2 P1 114.57(14) . . ? N3 P2 P1 88.67(14) . . ? F2B P2 P1 119.1(10) . . ? S1 N1 P1 121.8(2) . . ? P2 N2 P1 117.5(2) . . ? S1 N3 P2 122.3(2) . . ? C11 O2 P1 119.1(3) . . ? C13 O3 P2 119.4(3) . . ? C6 C1 C2 120.1(3) . . ? C6 C1 S1 121.1(3) . . ? C2 C1 S1 118.8(3) . . ? C1 C2 C3 119.8(3) . . ? C4 C3 C2 121.7(3) . . ? C3 C4 C5 117.1(3) . . ? C3 C4 C7 121.7(3) . . ? C5 C4 C7 121.1(3) . . ? C4 C5 C6 122.0(3) . . ? C1 C6 C5 119.3(3) . . ? C9 C7 C8 108.1(3) . . ? C9 C7 C4 111.6(3) . . ? C8 C7 C4 110.7(3) . . ? C9 C7 C10 109.4(4) . . ? C8 C7 C10 109.7(4) . . ? C4 C7 C10 107.3(3) . . ? O2 C11 C12 114.8(4) . . ? C11 C12 C13 118.2(3) . . ? O3 C13 C12 116.0(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F1B P1 P2 N2 -64(2) . . . . ? O2 P1 P2 N2 96.3(3) . . . . ? N1 P1 P2 N2 -151.7(3) . . . . ? F1A P1 P2 N2 -26.3(5) . . . . ? F1B P1 P2 F2A -11(3) . . . . ? O2 P1 P2 F2A 148.4(9) . . . . ? N2 P1 P2 F2A 52.1(9) . . . . ? N1 P1 P2 F2A -99.6(9) . . . . ? F1A P1 P2 F2A 25.8(12) . . . . ? F1B P1 P2 O3 -157(2) . . . . ? O2 P1 P2 O3 2.4(3) . . . . ? N2 P1 P2 O3 -93.9(3) . . . . ? N1 P1 P2 O3 114.4(2) . . . . ? F1A P1 P2 O3 -120.2(4) . . . . ? F1B P1 P2 N3 91(2) . . . . ? O2 P1 P2 N3 -109.3(2) . . . . ? N2 P1 P2 N3 154.4(3) . . . . ? N1 P1 P2 N3 2.69(17) . . . . ? F1A P1 P2 N3 128.1(4) . . . . ? F1B P1 P2 F2B -38(3) . . . . ? O2 P1 P2 F2B 121.8(8) . . . . ? N2 P1 P2 F2B 25.5(8) . . . . ? N1 P1 P2 F2B -126.2(8) . . . . ? F1A P1 P2 F2B -0.8(11) . . . . ? O1A S1 N1 P1 -157.4(5) . . . . ? O1B S1 N1 P1 -137.6(9) . . . . ? N3 S1 N1 P1 -25.3(3) . . . . ? C1 S1 N1 P1 92.4(3) . . . . ? F1B P1 N1 S1 -138.8(7) . . . . ? O2 P1 N1 S1 126.1(2) . . . . ? N2 P1 N1 S1 -3.5(3) . . . . ? F1A P1 N1 S1 -117.6(5) . . . . ? P2 P1 N1 S1 12.1(2) . . . . ? F2A P2 N2 P1 -146.7(5) . . . . ? O3 P2 N2 P1 100.4(2) . . . . ? N3 P2 N2 P1 -29.0(3) . . . . ? F2B P2 N2 P1 -157.9(6) . . . . ? F1B P1 N2 P2 145.5(7) . . . . ? O2 P1 N2 P2 -96.9(3) . . . . ? N1 P1 N2 P2 31.7(3) . . . . ? F1A P1 N2 P2 158.4(3) . . . . ? O1A S1 N3 P2 143.5(7) . . . . ? O1B S1 N3 P2 162.1(5) . . . . ? N1 S1 N3 P2 28.8(3) . . . . ? C1 S1 N3 P2 -89.1(2) . . . . ? N2 P2 N3 S1 -2.5(3) . . . . ? F2A P2 N3 S1 125.6(5) . . . . ? O3 P2 N3 S1 -133.0(2) . . . . ? F2B P2 N3 S1 107.6(9) . . . . ? P1 P2 N3 S1 -17.3(2) . . . . ? F1B P1 O2 C11 -153.7(13) . . . . ? N2 P1 O2 C11 69.4(4) . . . . ? N1 P1 O2 C11 -61.9(4) . . . . ? F1A P1 O2 C11 171.0(7) . . . . ? P2 P1 O2 C11 36.0(4) . . . . ? N2 P2 O3 C13 -71.8(4) . . . . ? F2A P2 O3 C13 163.0(7) . . . . ? N3 P2 O3 C13 60.9(4) . . . . ? F2B P2 O3 C13 -166.4(12) . . . . ? P1 P2 O3 C13 -37.2(4) . . . . ? O1A S1 C1 C6 -78.9(10) . . . . ? O1B S1 C1 C6 -118.1(12) . . . . ? N3 S1 C1 C6 143.8(3) . . . . ? N1 S1 C1 C6 22.9(3) . . . . ? O1A S1 C1 C2 99.4(10) . . . . ? O1B S1 C1 C2 60.1(12) . . . . ? N3 S1 C1 C2 -37.9(3) . . . . ? N1 S1 C1 C2 -158.9(3) . . . . ? C6 C1 C2 C3 -0.5(6) . . . . ? S1 C1 C2 C3 -178.8(3) . . . . ? C1 C2 C3 C4 0.0(6) . . . . ? C2 C3 C4 C5 0.2(5) . . . . ? C2 C3 C4 C7 -176.2(3) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C7 C4 C5 C6 176.5(3) . . . . ? C2 C1 C6 C5 0.8(5) . . . . ? S1 C1 C6 C5 179.0(3) . . . . ? C4 C5 C6 C1 -0.6(6) . . . . ? C3 C4 C7 C9 -20.3(5) . . . . ? C5 C4 C7 C9 163.5(4) . . . . ? C3 C4 C7 C8 -140.8(4) . . . . ? C5 C4 C7 C8 43.0(4) . . . . ? C3 C4 C7 C10 99.5(4) . . . . ? C5 C4 C7 C10 -76.8(4) . . . . ? P1 O2 C11 C12 -74.4(5) . . . . ? O2 C11 C12 C13 101.6(4) . . . . ? P2 O3 C13 C12 69.6(5) . . . . ? C11 C12 C13 O3 -97.4(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13B O1A 0.98 2.52 2.937(7) 105.3 2_665 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.537 _refine_diff_density_min -0.870 _refine_diff_density_rms 0.055 #===END