data_global _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Alder, Roger W.' 'Blake, Michael E.' 'Bufali, Simone' 'Butts, Craig' 'Orpen, A.' 'Schutz, Jan' 'Williams, Stuart J.' _publ_contact_author_name 'Dr Craig Butts' _publ_contact_author_address ; Dr Craig Butts School of Chemistry University of Exeter Exeter EX4 4QD UNITED KINGDOM ; data_dietpyr _database_code_CSD 155803 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H17 B0 F6 N2 P' _chemical_formula_weight 286.21 _chemical_melting_point ? _chemical_compound_source ? 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' 'B' 'B' 0.0013 0.0007 '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' '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1410(10) _cell_length_b 11.2300(10) _cell_length_c 14.131(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.220(10) _cell_angle_gamma 90.00 _cell_volume 1267.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 38 _cell_measurement_theta_min 9.389 _cell_measurement_theta_max 24.964 _exptl_crystal_description 'Irregular Block' _exptl_crystal_colour Colourless _exptl_crystal_size_max .56 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .46 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.500 _exptl_crystal_density_method ? _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3051 _diffrn_reflns_av_R_equivalents 0.0117 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.33 _diffrn_reflns_theta_max 27.29 _reflns_number_total 2212 _reflns_number_gt 1745 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens XSCANS' _computing_structure_solution 'Siemens SHELXTL' _computing_structure_refinement 'Siemens SHELXTL' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2212 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_all 0.1456 _refine_ls_wR_factor_ref 0.1319 _refine_ls_goodness_of_fit_all 1.048 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.048 _refine_ls_restrained_S_obs 1.078 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.2299(3) 0.0999(2) 0.31762(15) 0.0432(6) Uani 1 d . . C2 C 0.3912(3) 0.0840(2) 0.3258(2) 0.0403(6) Uani 1 d . . H2A H 0.4597(3) 0.1079(2) 0.3832(2) 0.048 Uiso 1 calc R . N3 N 0.4634(3) 0.0375(2) 0.2602(2) 0.0444(6) Uani 1 d . . C4 C 0.3636(5) -0.0090(3) 0.1704(2) 0.0609(9) Uani 1 d . . H4A H 0.3444(5) -0.0935(3) 0.1771(2) 0.073 Uiso 1 calc R . H4B H 0.4240(5) 0.0019(3) 0.1182(2) 0.073 Uiso 1 calc R . C5 C 0.1997(5) 0.0548(3) 0.1472(2) 0.0673(10) Uani 1 d . . H5A H 0.2181(5) 0.1352(3) 0.1264(2) 0.081 Uiso 1 calc R . H5B H 0.1273(5) 0.0145(3) 0.0942(2) 0.081 Uiso 1 calc R . C6 C 0.1147(4) 0.0602(3) 0.2313(2) 0.0591(9) Uani 1 d . . H6A H 0.0206(4) 0.1146(3) 0.2172(2) 0.071 Uiso 1 calc R . H6B H 0.0718(4) -0.0180(3) 0.2426(2) 0.071 Uiso 1 calc R . C7 C 0.6452(4) 0.0168(3) 0.2807(3) 0.0590(8) Uani 1 d . . H7A H 0.6975(4) 0.0698(3) 0.3321(3) 0.071 Uiso 1 calc R . H7B H 0.6901(4) 0.0354(3) 0.2237(3) 0.071 Uiso 1 calc R . C7' C 0.1608(4) 0.1465(3) 0.3992(2) 0.0593(9) Uani 1 d . . H7'A H 0.2458(4) 0.1409(3) 0.4576(2) 0.071 Uiso 1 calc R . H7'B H 0.0670(4) 0.0971(3) 0.4078(2) 0.071 Uiso 1 calc R . C8 C 0.6880(5) -0.1098(3) 0.3102(3) 0.0719(11) Uani 1 d . . H8A H 0.8074(5) -0.1197(3) 0.3229(3) 0.108 Uiso 1 calc R . H8B H 0.6382(5) -0.1624(3) 0.2590(3) 0.108 Uiso 1 calc R . H8C H 0.6456(5) -0.1281(3) 0.3673(3) 0.108 Uiso 1 calc R . C8' C 0.1035(5) 0.2723(4) 0.3858(3) 0.0774(11) Uani 1 d . . H8'A H 0.0600(5) 0.2976(4) 0.4410(3) 0.116 Uiso 1 calc R . H8'B H 0.0173(5) 0.2783(4) 0.3290(3) 0.116 Uiso 1 calc R . H8'C H 0.1962(5) 0.3221(4) 0.3788(3) 0.116 Uiso 1 calc R . P10 P 0.71330(9) 0.25959(7) 0.05588(5) 0.0451(3) Uani 1 d . . F11 F 0.8937(3) 0.3149(3) 0.0788(2) 0.1120(10) Uani 1 d . . F12 F 0.7083(4) 0.2653(2) 0.16658(15) 0.1042(9) Uani 1 d . . F13 F 0.7198(3) 0.2561(2) -0.05538(13) 0.0812(7) Uani 1 d . . F14 F 0.6315(3) 0.3889(2) 0.04280(13) 0.0716(6) Uani 1 d . . F15 F 0.7897(3) 0.1296(2) 0.06738(14) 0.0851(7) Uani 1 d . . F16 F 0.5328(3) 0.2052(2) 0.0316(2) 0.1042(9) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0418(13) 0.0460(13) 0.0389(12) 0.0031(10) 0.0008(10) 0.0041(11) C2 0.045(2) 0.0343(13) 0.0382(13) 0.0002(11) -0.0002(11) 0.0017(12) N3 0.0472(14) 0.0369(12) 0.0489(13) -0.0039(10) 0.0083(11) 0.0005(11) C4 0.083(2) 0.054(2) 0.046(2) -0.0115(14) 0.011(2) -0.003(2) C5 0.077(2) 0.073(2) 0.042(2) -0.008(2) -0.012(2) -0.001(2) C6 0.048(2) 0.065(2) 0.056(2) -0.002(2) -0.0106(14) -0.002(2) C7 0.051(2) 0.052(2) 0.077(2) -0.006(2) 0.021(2) 0.005(2) C7' 0.061(2) 0.069(2) 0.049(2) 0.005(2) 0.0142(15) 0.011(2) C8 0.065(2) 0.073(2) 0.084(3) 0.023(2) 0.031(2) 0.023(2) C8' 0.091(3) 0.073(3) 0.077(3) 0.001(2) 0.036(2) 0.022(2) P10 0.0490(5) 0.0440(4) 0.0382(4) -0.0040(3) -0.0013(3) 0.0060(3) F11 0.0608(14) 0.126(2) 0.142(2) -0.046(2) 0.0022(14) -0.0239(15) F12 0.174(3) 0.096(2) 0.0442(11) 0.0049(11) 0.0252(14) 0.046(2) F13 0.131(2) 0.0683(13) 0.0434(10) -0.0049(9) 0.0159(11) 0.0199(13) F14 0.104(2) 0.0454(10) 0.0587(11) -0.0072(8) -0.0016(10) 0.0190(10) F15 0.112(2) 0.0653(13) 0.0688(13) -0.0009(10) -0.0053(12) 0.0430(13) F16 0.0639(14) 0.080(2) 0.166(3) -0.018(2) 0.0179(14) -0.0173(13) _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 N1 C2 1.308(3) . ? N1 C6 1.456(3) . ? N1 C7' 1.474(4) . ? C2 N3 1.300(3) . ? N3 C4 1.463(4) . ? N3 C7 1.471(4) . ? C4 C5 1.493(5) . ? C5 C6 1.488(5) . ? C7 C8 1.503(5) . ? C7' C8' 1.488(5) . ? P10 F16 1.566(2) . ? P10 F11 1.569(2) . ? P10 F12 1.574(2) . ? P10 F15 1.583(2) . ? P10 F13 1.584(2) . ? P10 F14 1.593(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 C2 N1 C6 120.3(2) . . ? C2 N1 C7' 120.6(2) . . ? C6 N1 C7' 118.8(2) . . ? N3 C2 N1 125.3(2) . . ? C2 N3 C4 120.7(2) . . ? C2 N3 C7 120.0(2) . . ? C4 N3 C7 118.9(3) . . ? N3 C4 C5 109.9(2) . . ? C6 C5 C4 112.3(3) . . ? N1 C6 C5 110.9(3) . . ? N3 C7 C8 112.0(3) . . ? N1 C7' C8' 113.3(3) . . ? F16 P10 F11 179.2(2) . . ? F16 P10 F12 91.7(2) . . ? F11 P10 F12 89.0(2) . . ? F16 P10 F15 89.74(14) . . ? F11 P10 F15 90.6(2) . . ? F12 P10 F15 91.21(12) . . ? F16 P10 F13 89.06(15) . . ? F11 P10 F13 90.24(15) . . ? F12 P10 F13 178.99(14) . . ? F15 P10 F13 89.47(11) . . ? F16 P10 F14 88.68(13) . . ? F11 P10 F14 90.94(14) . . ? F12 P10 F14 89.26(11) . . ? F15 P10 F14 178.37(12) . . ? F13 P10 F14 90.08(11) . . ? _refine_diff_density_max 0.350 _refine_diff_density_min -0.384 _refine_diff_density_rms 0.072 #===END data_tipts _database_code_CSD 155804 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H29 F3 N2 O3 S' _chemical_formula_weight 362.45 _chemical_melting_point ? _chemical_compound_source ? 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' '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 8.996(2) _cell_length_b 9.238(2) _cell_length_c 11.992(2) _cell_angle_alpha 90.02(2) _cell_angle_beta 91.36(2) _cell_angle_gamma 112.50(2) _cell_volume 920.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 81 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Rectangular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method ? _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5877 _diffrn_reflns_av_R_equivalents 0.0175 _diffrn_reflns_av_sigmaI/netI 0.0509 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.70 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4034 _reflns_number_gt 2718 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SAINT (Siemens, 1995b)' _computing_data_reduction 'SAINT (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4034 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0800 _refine_ls_R_factor_gt 0.0572 _refine_ls_wR_factor_all 0.1662 _refine_ls_wR_factor_ref 0.1569 _refine_ls_goodness_of_fit_all 1.129 _refine_ls_goodness_of_fit_ref 1.312 _refine_ls_restrained_S_all 1.129 _refine_ls_restrained_S_obs 1.312 _refine_ls_shift/su_max -0.014 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.22850(8) 0.34086(8) 0.78178(5) 0.0283(2) Uani 1 d . . F1 F 0.3547(2) 0.1268(2) 0.7836(2) 0.0540(5) Uani 1 d . . O1 O 0.2006(3) 0.3157(2) 0.8981(2) 0.0421(5) Uani 1 d . . N1 N 0.3226(2) 0.1769(2) 0.2256(2) 0.0231(5) Uani 1 d . . F2 F 0.1021(2) 0.0351(2) 0.7528(2) 0.0666(6) Uani 1 d . . O2 O 0.0966(3) 0.3493(3) 0.7175(2) 0.0591(7) Uani 1 d . . C2 C 0.2460(3) 0.2698(3) 0.2024(2) 0.0178(5) Uani 1 d . . H2B H 0.2338(3) 0.2833(3) 0.1247(2) 0.021 Uiso 1 calc R . F3 F 0.2602(3) 0.1572(2) 0.62465(15) 0.0648(6) Uani 1 d . . O3 O 0.3834(3) 0.4524(3) 0.7534(2) 0.0598(7) Uani 1 d . . N3 N 0.1828(2) 0.3478(2) 0.2647(2) 0.0190(4) Uani 1 d . . C4D C 0.3611(3) 0.0954(3) 0.1288(2) 0.0210(5) Uani 1 d . . H4DA H 0.4102(3) 0.0231(3) 0.1600(2) 0.025 Uiso 1 calc R . C4C C 0.3870(4) 0.1548(4) 0.3378(2) 0.0454(9) Uani 1 d . . H4CA H 0.3737(4) 0.2329(4) 0.3903(2) 0.054 Uiso 1 calc R . C4B C 0.1169(3) 0.4539(3) 0.2044(2) 0.0206(5) Uani 1 d . . H4BA H 0.0797(3) 0.5096(3) 0.2622(2) 0.025 Uiso 1 calc R . C4A C 0.1699(3) 0.3446(3) 0.3888(2) 0.0297(6) Uani 1 d . . H4AA H 0.2020(3) 0.2587(3) 0.4172(2) 0.036 Uiso 1 calc R . C5H C 0.2100(3) -0.0042(3) 0.0629(2) 0.0308(6) Uani 1 d . . H5HA H 0.1334(3) -0.0778(3) 0.1131(2) 0.046 Uiso 1 calc R . H5HB H 0.2382(3) -0.0628(3) 0.0045(2) 0.046 Uiso 1 calc R . H5HC H 0.1610(3) 0.0637(3) 0.0286(2) 0.046 Uiso 1 calc R . C5G C 0.4854(3) 0.2124(3) 0.0561(2) 0.0294(6) Uani 1 d . . H5GA H 0.5804(3) 0.2738(3) 0.1019(2) 0.044 Uiso 1 calc R . H5GB H 0.4395(3) 0.2828(3) 0.0217(2) 0.044 Uiso 1 calc R . H5GC H 0.5167(3) 0.1563(3) -0.0024(2) 0.044 Uiso 1 calc R . C5F C 0.5668(4) 0.1852(4) 0.3353(3) 0.0506(9) Uani 1 d . . H5FA H 0.6263(4) 0.2910(4) 0.3076(3) 0.076 Uiso 1 calc R . H5FB H 0.5830(4) 0.1083(4) 0.2859(3) 0.076 Uiso 1 calc R . H5FC H 0.6060(4) 0.1758(4) 0.4108(3) 0.076 Uiso 1 calc R . C5E C 0.2883(4) -0.0052(5) 0.3792(3) 0.0650(11) Uani 1 d . . H5EA H 0.1747(4) -0.0192(5) 0.3793(3) 0.098 Uiso 1 calc R . H5EB H 0.3243(4) -0.0170(5) 0.4552(3) 0.098 Uiso 1 calc R . H5EC H 0.3013(4) -0.0843(5) 0.3302(3) 0.098 Uiso 1 calc R . C5D C -0.0288(3) 0.3599(3) 0.1312(2) 0.0291(6) Uani 1 d . . H5DA H -0.1092(3) 0.2816(3) 0.1765(2) 0.044 Uiso 1 calc R . H5DB H 0.0044(3) 0.3069(3) 0.0716(2) 0.044 Uiso 1 calc R . H5DC H -0.0755(3) 0.4305(3) 0.0982(2) 0.044 Uiso 1 calc R . C5C C 0.2469(3) 0.5780(3) 0.1391(2) 0.0311(6) Uani 1 d . . H5CA H 0.3381(3) 0.6354(3) 0.1894(2) 0.047 Uiso 1 calc R . H5CB H 0.2033(3) 0.6511(3) 0.1063(2) 0.047 Uiso 1 calc R . H5CC H 0.2832(3) 0.5275(3) 0.0797(2) 0.047 Uiso 1 calc R . C5B C -0.0037(4) 0.3079(4) 0.4232(2) 0.0437(8) Uani 1 d . . H5BA H -0.0750(4) 0.2087(4) 0.3886(2) 0.065 Uiso 1 calc R . H5BB H -0.0371(4) 0.3923(4) 0.3986(2) 0.065 Uiso 1 calc R . H5BC H -0.0101(4) 0.2992(4) 0.5046(2) 0.065 Uiso 1 calc R . C5A C 0.2850(3) 0.4966(4) 0.4399(2) 0.0471(9) Uani 1 d . . H5AA H 0.3945(3) 0.5164(4) 0.4162(2) 0.071 Uiso 1 calc R . H5AB H 0.2812(3) 0.4896(4) 0.5214(2) 0.071 Uiso 1 calc R . H5AC H 0.2541(3) 0.5826(4) 0.4154(2) 0.071 Uiso 1 calc R . C6 C 0.2368(3) 0.1572(3) 0.7334(2) 0.0313(6) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0386(4) 0.0271(4) 0.0259(4) -0.0011(3) 0.0013(3) 0.0201(3) F1 0.0632(13) 0.0535(12) 0.0647(13) -0.0132(10) -0.0155(10) 0.0449(11) O1 0.0676(15) 0.0454(12) 0.0238(11) -0.0034(9) 0.0036(9) 0.0333(12) N1 0.0297(12) 0.0304(11) 0.0169(10) 0.0002(8) 0.0002(8) 0.0200(10) F2 0.0550(13) 0.0339(10) 0.098(2) -0.0190(10) 0.0077(11) 0.0020(10) O2 0.079(2) 0.088(2) 0.0422(13) -0.0137(12) -0.0167(12) 0.068(2) C2 0.0182(12) 0.0191(12) 0.0167(11) 0.0008(9) -0.0001(9) 0.0078(10) F3 0.115(2) 0.0722(14) 0.0303(10) -0.0117(9) 0.0057(10) 0.0613(14) O3 0.062(2) 0.0296(12) 0.081(2) 0.0037(11) 0.0233(13) 0.0096(12) N3 0.0240(11) 0.0209(10) 0.0157(10) -0.0003(8) 0.0004(8) 0.0126(9) C4D 0.0247(13) 0.0217(12) 0.0213(12) -0.0009(9) 0.0010(10) 0.0140(11) C4C 0.078(2) 0.064(2) 0.0220(15) 0.0023(14) 0.0027(14) 0.058(2) C4B 0.0257(13) 0.0202(12) 0.0205(12) -0.0012(9) -0.0018(10) 0.0142(11) C4A 0.048(2) 0.0357(15) 0.0170(13) 0.0012(10) 0.0004(11) 0.0293(14) C5H 0.032(2) 0.0259(14) 0.034(2) -0.0073(11) -0.0038(12) 0.0104(12) C5G 0.0255(14) 0.0323(14) 0.0303(14) 0.0001(11) 0.0045(11) 0.0108(12) C5F 0.059(2) 0.042(2) 0.055(2) -0.008(2) -0.028(2) 0.026(2) C5E 0.049(2) 0.089(3) 0.060(2) 0.038(2) 0.009(2) 0.028(2) C5D 0.0250(14) 0.0355(15) 0.0300(15) -0.0027(11) -0.0049(11) 0.0153(12) C5C 0.037(2) 0.0247(14) 0.034(2) 0.0063(11) -0.0002(12) 0.0146(12) C5B 0.051(2) 0.037(2) 0.035(2) -0.0033(13) 0.0190(14) 0.006(2) C5A 0.032(2) 0.074(2) 0.032(2) -0.021(2) -0.0071(13) 0.018(2) C6 0.035(2) 0.0320(15) 0.030(2) -0.0053(12) -0.0008(12) 0.0173(13) _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 O2 1.427(2) . ? S1 O1 1.427(2) . ? S1 O3 1.429(2) . ? S1 C6 1.822(3) . ? F1 C6 1.329(3) . ? N1 C2 1.316(3) . ? N1 C4C 1.496(3) . ? N1 C4D 1.500(3) . ? F2 C6 1.328(3) . ? C2 N3 1.317(3) . ? F3 C6 1.325(3) . ? N3 C4A 1.495(3) . ? N3 C4B 1.503(3) . ? C4D C5G 1.517(3) . ? C4D C5H 1.520(3) . ? C4C C5E 1.496(5) . ? C4C C5F 1.533(4) . ? C4B C5C 1.520(4) . ? C4B C5D 1.522(3) . ? C4A C5A 1.509(4) . ? C4A C5B 1.533(4) . ? 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 O2 S1 O1 114.97(14) . . ? O2 S1 O3 115.2(2) . . ? O1 S1 O3 115.84(15) . . ? O2 S1 C6 102.48(14) . . ? O1 S1 C6 103.25(13) . . ? O3 S1 C6 102.22(13) . . ? C2 N1 C4C 126.3(2) . . ? C2 N1 C4D 116.8(2) . . ? C4C N1 C4D 116.7(2) . . ? N1 C2 N3 133.3(2) . . ? C2 N3 C4A 127.7(2) . . ? C2 N3 C4B 116.5(2) . . ? C4A N3 C4B 115.9(2) . . ? N1 C4D C5G 110.7(2) . . ? N1 C4D C5H 111.6(2) . . ? C5G C4D C5H 112.3(2) . . ? N1 C4C C5E 109.2(3) . . ? N1 C4C C5F 111.8(2) . . ? C5E C4C C5F 112.4(3) . . ? N3 C4B C5C 111.2(2) . . ? N3 C4B C5D 111.0(2) . . ? C5C C4B C5D 112.3(2) . . ? N3 C4A C5A 110.5(2) . . ? N3 C4A C5B 111.2(2) . . ? C5A C4A C5B 111.7(2) . . ? F3 C6 F1 106.8(2) . . ? F3 C6 F2 106.7(2) . . ? F1 C6 F2 106.1(2) . . ? F3 C6 S1 112.3(2) . . ? F1 C6 S1 112.3(2) . . ? F2 C6 S1 112.2(2) . . ? 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 C4C N1 C2 N3 -11.8(4) . . . . ? C4D N1 C2 N3 173.6(2) . . . . ? N1 C2 N3 C4A -4.6(4) . . . . ? N1 C2 N3 C4B 174.8(2) . . . . ? C2 N1 C4D C5G 67.9(3) . . . . ? C4C N1 C4D C5G -107.2(3) . . . . ? C2 N1 C4D C5H -58.0(3) . . . . ? C4C N1 C4D C5H 126.9(2) . . . . ? C2 N1 C4C C5E 109.8(3) . . . . ? C4D N1 C4C C5E -75.6(3) . . . . ? C2 N1 C4C C5F -125.1(3) . . . . ? C4D N1 C4C C5F 49.5(3) . . . . ? C2 N3 C4B C5C -59.4(3) . . . . ? C4A N3 C4B C5C 120.1(2) . . . . ? C2 N3 C4B C5D 66.4(3) . . . . ? C4A N3 C4B C5D -114.1(2) . . . . ? C2 N3 C4A C5A 108.4(3) . . . . ? C4B N3 C4A C5A -71.0(3) . . . . ? C2 N3 C4A C5B -127.0(3) . . . . ? C4B N3 C4A C5B 53.6(3) . . . . ? O2 S1 C6 F3 59.4(2) . . . . ? O1 S1 C6 F3 179.1(2) . . . . ? O3 S1 C6 F3 -60.3(2) . . . . ? O2 S1 C6 F1 179.7(2) . . . . ? O1 S1 C6 F1 -60.5(2) . . . . ? O3 S1 C6 F1 60.1(2) . . . . ? O2 S1 C6 F2 -60.8(2) . . . . ? O1 S1 C6 F2 58.9(2) . . . . ? O3 S1 C6 F2 179.5(2) . . . . ? _refine_diff_density_max 1.062 _refine_diff_density_min -0.590 _refine_diff_density_rms 0.068 #===END data_cpb2 _database_code_CSD 155805 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H25 F6 N2 P' _chemical_formula_weight 342.31 _chemical_melting_point ? _chemical_compound_source ? 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' '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.610(2) _cell_length_b 12.226(3) _cell_length_c 14.090(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1655.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 5.12 _cell_measurement_theta_max 12.51 _exptl_crystal_description Hexagonal_rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.54 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.374 _exptl_crystal_density_method ? _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 0.220 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 1109 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0751 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max -2 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 6.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1109 _reflns_number_gt 682 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.14(41) _refine_ls_number_reflns 1109 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_all 0.1777 _refine_ls_wR_factor_ref 0.1725 _refine_ls_goodness_of_fit_all 1.026 _refine_ls_goodness_of_fit_ref 1.354 _refine_ls_restrained_S_all 1.026 _refine_ls_restrained_S_ 1.354 _refine_ls_shift/su_max 0.023 _refine_ls_shift/esd_mean 0.001 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.0163(2) 0.4487(3) 0.4564(2) 0.0628(9) Uani 1 d . . F1 F 0.0337(9) 0.4899(13) 0.5595(9) 0.156(4) Uani 1 d . . F2 F -0.1183(7) 0.5128(12) 0.4380(9) 0.163(5) Uani 1 d . . F3 F 0.1123(7) 0.5394(9) 0.4154(7) 0.120(3) Uani 1 d . . F4 F 0.1490(6) 0.3785(9) 0.4716(7) 0.128(3) Uani 1 d . . F5 F -0.0774(5) 0.3505(8) 0.4936(6) 0.103(3) Uani 1 d . . F6 F 0.0021(7) 0.3996(10) 0.3508(6) 0.116(3) Uani 1 d . . N2 N -0.0607(5) 0.6002(7) 0.9040(5) 0.052(2) Uani 1 d . . N8 N -0.0482(5) 0.5183(6) 1.0587(6) 0.054(2) Uani 1 d . . C1 C -0.0761(6) 0.5965(7) 0.9970(6) 0.047(2) Uani 1 d . . H1 H -0.1128(6) 0.6598(7) 1.0236(6) 0.057 Uiso 1 calc R . C3 C 0.0253(7) 0.5253(9) 0.8451(7) 0.067(3) Uani 1 d . . H3A H -0.0344(7) 0.4768(9) 0.8090(7) 0.080 Uiso 1 calc R . H3B H 0.0844(7) 0.4811(9) 0.8857(7) 0.080 Uiso 1 calc R . C4 C 0.1137(8) 0.5923(12) 0.7786(8) 0.083(4) Uani 1 d . . H4A H 0.1607(8) 0.5433(12) 0.7349(8) 0.099 Uiso 1 calc R . H4B H 0.1846(8) 0.6298(12) 0.8152(8) 0.099 Uiso 1 calc R . C5 C 0.0326(8) 0.6760(12) 0.7219(8) 0.076(3) Uani 1 d . . H5A H 0.0963(8) 0.7208(12) 0.6853(8) 0.091 Uiso 1 calc R . H5B H -0.0294(8) 0.6390(12) 0.6780(8) 0.091 Uiso 1 calc R . C6 C -0.0493(7) 0.7461(9) 0.7864(7) 0.065(3) Uani 1 d . . H6A H 0.0139(7) 0.7912(9) 0.8232(7) 0.078 Uiso 1 calc R . H6B H -0.1076(7) 0.7943(9) 0.7490(7) 0.078 Uiso 1 calc R . C7 C -0.1376(6) 0.6830(9) 0.8517(7) 0.061(2) Uani 1 d . . H7A H -0.1810(6) 0.7327(9) 0.8964(7) 0.073 Uiso 1 calc R . H7B H -0.2110(6) 0.6477(9) 0.8157(7) 0.073 Uiso 1 calc R . C9 C -0.0366(7) 0.4013(10) 1.0370(9) 0.065(2) Uani 1 d . . H9 H -0.0509(7) 0.3924(10) 0.9685(9) 0.078 Uiso 1 calc R . C10 C 0.1060(8) 0.3548(10) 1.0609(12) 0.099(5) Uani 1 d . . H10A H 0.1035(37) 0.2765(14) 1.0556(88) 0.148 Uiso 1 calc R . H10B H 0.1306(58) 0.3749(87) 1.1246(34) 0.148 Uiso 1 calc R . H10C H 0.1738(24) 0.3836(83) 1.0176(59) 0.148 Uiso 1 calc R . C11 C -0.1505(8) 0.3366(9) 1.0877(11) 0.087(4) Uani 1 d . . H11A H -0.1241(48) 0.3249(69) 1.1526(18) 0.131 Uiso 1 calc R . H11B H -0.1628(68) 0.2673(33) 1.0568(40) 0.131 Uiso 1 calc R . H11C H -0.2362(27) 0.3769(37) 1.0856(64) 0.131 Uiso 1 calc R . C12 C -0.0403(6) 0.5510(10) 1.1600(7) 0.060(2) Uani 1 d . . H12 H -0.0266(6) 0.4838(10) 1.1968(7) 0.072 Uiso 1 calc R . C13 C 0.0853(8) 0.6216(11) 1.1769(9) 0.080(3) Uani 1 d . . H13A H 0.1628(25) 0.5932(45) 1.1417(50) 0.120 Uiso 1 calc R . H13B H 0.1073(56) 0.6218(58) 1.2434(12) 0.120 Uiso 1 calc R . H13C H 0.0659(33) 0.6949(21) 1.1564(59) 0.120 Uiso 1 calc R . C14 C -0.1749(8) 0.6023(12) 1.1947(9) 0.086(4) Uani 1 d . . H14A H -0.1862(53) 0.6731(38) 1.1661(56) 0.129 Uiso 1 calc R . H14B H -0.1718(46) 0.6099(78) 1.2624(11) 0.129 Uiso 1 calc R . H14C H -0.2519(14) 0.5564(44) 1.1773(66) 0.129 Uiso 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 P1 0.0689(11) 0.065(2) 0.0545(15) -0.001(2) -0.0024(8) -0.0029(10) F1 0.237(8) 0.143(12) 0.087(8) -0.058(9) -0.010(5) -0.036(7) F2 0.123(4) 0.184(12) 0.182(11) -0.022(9) -0.013(5) 0.076(6) F3 0.139(4) 0.089(6) 0.131(8) 0.013(6) -0.010(4) -0.042(4) F4 0.107(4) 0.153(9) 0.125(8) 0.036(7) 0.000(4) 0.039(4) F5 0.107(3) 0.115(8) 0.087(5) 0.013(5) -0.002(3) -0.037(4) F6 0.183(6) 0.111(7) 0.054(5) -0.001(5) -0.005(3) -0.026(5) N2 0.054(3) 0.047(5) 0.054(5) -0.002(4) -0.001(2) 0.005(2) N8 0.053(3) 0.054(5) 0.054(5) 0.000(4) -0.002(2) 0.001(2) C1 0.052(3) 0.041(5) 0.050(5) 0.002(4) 0.004(3) 0.001(3) C3 0.081(4) 0.064(7) 0.055(6) -0.010(5) 0.006(3) 0.013(4) C4 0.076(4) 0.108(10) 0.064(7) 0.003(7) 0.016(4) 0.027(5) C5 0.077(5) 0.098(9) 0.052(6) 0.004(7) 0.011(4) 0.003(5) C6 0.069(4) 0.064(7) 0.061(7) 0.002(6) 0.004(3) 0.003(4) C7 0.059(3) 0.066(6) 0.058(6) 0.008(5) 0.001(3) 0.011(3) C9 0.074(4) 0.060(6) 0.061(6) 0.001(6) 0.003(4) 0.009(4) C10 0.081(5) 0.062(8) 0.154(15) 0.019(9) 0.019(6) 0.025(4) C11 0.083(5) 0.052(6) 0.127(11) 0.014(7) -0.002(5) -0.019(4) C12 0.068(4) 0.062(6) 0.051(6) 0.006(6) -0.001(3) -0.003(4) C13 0.092(5) 0.080(9) 0.067(8) 0.001(7) -0.022(4) -0.010(5) C14 0.097(5) 0.094(10) 0.066(8) 0.006(7) 0.021(4) 0.024(5) _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 F2 1.534(8) . ? P1 F1 1.547(12) . ? P1 F3 1.553(9) . ? P1 F4 1.553(8) . ? P1 F5 1.590(8) . ? P1 F6 1.611(9) . ? N2 C1 1.319(11) . ? N2 C7 1.454(12) . ? N2 C3 1.487(12) . ? N8 C1 1.319(11) . ? N8 C9 1.467(13) . ? N8 C12 1.485(13) . ? C3 C4 1.507(15) . ? C4 C5 1.51(2) . ? C5 C6 1.476(14) . ? C6 C7 1.470(13) . ? C9 C10 1.521(12) . ? C9 C11 1.528(15) . ? C12 C13 1.502(14) . ? C12 C14 1.519(13) . ? 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 F2 P1 F1 94.8(7) . . ? F2 P1 F3 94.2(7) . . ? F1 P1 F3 93.0(6) . . ? F2 P1 F4 176.7(7) . . ? F1 P1 F4 87.8(6) . . ? F3 P1 F4 87.6(5) . . ? F2 P1 F5 87.9(6) . . ? F1 P1 F5 89.9(6) . . ? F3 P1 F5 176.2(6) . . ? F4 P1 F5 90.1(6) . . ? F2 P1 F6 87.9(6) . . ? F1 P1 F6 176.8(8) . . ? F3 P1 F6 88.4(5) . . ? F4 P1 F6 89.4(5) . . ? F5 P1 F6 88.5(5) . . ? C1 N2 C7 118.1(7) . . ? C1 N2 C3 126.5(8) . . ? C7 N2 C3 115.4(8) . . ? C1 N8 C9 125.8(9) . . ? C1 N8 C12 116.7(8) . . ? C9 N8 C12 117.3(9) . . ? N8 C1 N2 131.0(9) . . ? N2 C3 C4 109.1(9) . . ? C3 C4 C5 113.9(6) . . ? C6 C5 C4 110.0(9) . . ? C7 C6 C5 112.9(10) . . ? N2 C7 C6 112.9(5) . . ? N8 C9 C10 112.8(8) . . ? N8 C9 C11 110.7(8) . . ? C10 C9 C11 110.4(11) . . ? N8 C12 C13 110.4(7) . . ? N8 C12 C14 112.1(7) . . ? C13 C12 C14 113.3(11) . . ? 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 C9 N8 C1 N2 -22.5(12) . . . . ? C12 N8 C1 N2 163.2(7) . . . . ? C7 N2 C1 N8 161.9(7) . . . . ? C3 N2 C1 N8 -16.2(13) . . . . ? C1 N2 C3 C4 -131.7(9) . . . . ? C7 N2 C3 C4 50.2(10) . . . . ? N2 C3 C4 C5 -51.3(13) . . . . ? C3 C4 C5 C6 53.9(14) . . . . ? C4 C5 C6 C7 -53.1(11) . . . . ? C1 N2 C7 C6 129.9(9) . . . . ? C3 N2 C7 C6 -51.9(11) . . . . ? C5 C6 C7 N2 52.8(11) . . . . ? C1 N8 C9 C10 119.9(10) . . . . ? C12 N8 C9 C10 -65.8(11) . . . . ? C1 N8 C9 C11 -115.9(10) . . . . ? C12 N8 C9 C11 58.4(10) . . . . ? C1 N8 C12 C13 -68.6(9) . . . . ? C9 N8 C12 C13 116.6(9) . . . . ? C1 N8 C12 C14 58.7(11) . . . . ? C9 N8 C12 C14 -116.1(10) . . . . ? _refine_diff_density_max 0.303 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.087 #===END data_pbcn _database_code_CSD 155806 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C11 H21 B F4 N2' _chemical_formula_weight 268.11 _chemical_melting_point ? _chemical_compound_source ? 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' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 18.0860(3) _cell_length_b 9.73390(10) _cell_length_c 7.6426(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1345.46(4) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 181 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.5 _exptl_crystal_description Rectangular _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.70 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method ? _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7836 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0220 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.46 _reflns_number_total 1532 _reflns_number_gt 1144 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1532 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0668 _refine_ls_R_factor_gt 0.0525 _refine_ls_wR_factor_all 0.1657 _refine_ls_wR_factor_ref 0.1568 _refine_ls_goodness_of_fit_all 1.112 _refine_ls_goodness_of_fit_ref 1.227 _refine_ls_restrained_S_all 1.112 _refine_ls_restrained_S_obs 1.227 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.43572(7) 0.79309(12) 0.2189(2) 0.0224(3) Uani 1 d . . C2 C 0.5000 0.8508(2) 0.2500 0.0222(4) Uani 1 d S . H2A H 0.5000 0.9484(2) 0.2500 0.027 Uiso 1 calc SR . C4 C 0.37883(8) 0.8747(2) 0.1280(2) 0.0302(4) Uani 1 d . . H4A H 0.37325(8) 0.8405(2) 0.0067(2) 0.036 Uiso 1 calc R . H4B H 0.39494(8) 0.9718(2) 0.1220(2) 0.036 Uiso 1 calc R . C5 C 0.30443(9) 0.8665(2) 0.2215(2) 0.0352(4) Uani 1 d . . H5A H 0.30804(9) 0.9129(2) 0.3365(2) 0.042 Uiso 1 calc R . H5B H 0.26643(9) 0.9148(2) 0.1514(2) 0.042 Uiso 1 calc R . C6 C 0.28147(9) 0.7180(2) 0.2479(2) 0.0349(4) Uani 1 d . . H6A H 0.27413(9) 0.6731(2) 0.1329(2) 0.042 Uiso 1 calc R . H6B H 0.23418(9) 0.7142(2) 0.3130(2) 0.042 Uiso 1 calc R . C7 C 0.34144(8) 0.6429(2) 0.3502(2) 0.0340(4) Uani 1 d . . H7A H 0.32677(8) 0.5456(2) 0.3657(2) 0.041 Uiso 1 calc R . H7B H 0.34617(8) 0.6847(2) 0.4677(2) 0.041 Uiso 1 calc R . C8 C 0.41605(8) 0.6489(2) 0.2574(2) 0.0272(4) Uani 1 d . . H8A H 0.45455(8) 0.6071(2) 0.3326(2) 0.033 Uiso 1 calc R . H8B H 0.41360(8) 0.5958(2) 0.1470(2) 0.033 Uiso 1 calc R . B1 B 0.5000 0.2652(3) 0.2500 0.0420(8) Uani 1 d S . F1 F 0.54758(12) 0.3468(2) 0.1589(2) 0.1100(9) Uani 1 d . . F2 F 0.46509(9) 0.1800(2) 0.1310(2) 0.0738(5) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0206(7) 0.0200(6) 0.0266(7) 0.0019(5) -0.0011(5) 0.0016(5) C2 0.0247(10) 0.0195(10) 0.0224(10) 0.000 0.0008(7) 0.000 C4 0.0260(8) 0.0252(8) 0.0395(9) 0.0039(6) -0.0067(6) 0.0026(6) C5 0.0239(8) 0.0358(9) 0.0458(10) -0.0070(7) -0.0031(7) 0.0062(7) C6 0.0224(8) 0.0416(11) 0.0408(10) -0.0016(8) 0.0009(6) -0.0030(7) C7 0.0251(8) 0.0385(9) 0.0382(9) 0.0060(7) 0.0025(7) -0.0074(7) C8 0.0250(8) 0.0207(8) 0.0358(9) 0.0036(6) 0.0001(6) -0.0030(6) B1 0.073(2) 0.0216(13) 0.0309(14) 0.000 0.0120(14) 0.000 F1 0.184(2) 0.0481(9) 0.0981(13) -0.0250(8) 0.0859(14) -0.0509(10) F2 0.1001(12) 0.0581(9) 0.0633(9) 0.0069(7) -0.0264(8) -0.0174(8) _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 N1 C2 1.313(2) . ? N1 C4 1.474(2) . ? N1 C8 1.478(2) . ? C2 N1 1.313(2) 3_655 ? C4 C5 1.526(2) . ? C5 C6 1.518(3) . ? C6 C7 1.524(2) . ? C7 C8 1.526(2) . ? B1 F1 1.362(2) 3_655 ? B1 F1 1.362(2) . ? B1 F2 1.384(2) . ? B1 F2 1.384(2) 3_655 ? 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 C2 N1 C4 118.21(13) . . ? C2 N1 C8 125.70(13) . . ? C4 N1 C8 115.98(12) . . ? N1 C2 N1 129.3(2) 3_655 . ? N1 C4 C5 111.51(13) . . ? C6 C5 C4 110.69(14) . . ? C5 C6 C7 109.31(14) . . ? C6 C7 C8 111.87(13) . . ? N1 C8 C7 110.00(13) . . ? F1 B1 F1 108.7(2) 3_655 . ? F1 B1 F2 113.41(14) 3_655 . ? F1 B1 F2 107.58(11) . . ? F1 B1 F2 107.58(11) 3_655 3_655 ? F1 B1 F2 113.40(14) . 3_655 ? F2 B1 F2 106.3(2) . 3_655 ? _refine_diff_density_max 0.571 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.051 #===END data_didicat _database_code_CSD 155807 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H30 F6 N2 O7 S2' _chemical_formula_weight 540.54 _chemical_melting_point ? _chemical_compound_source ? 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3218(13) _cell_length_b 17.900(2) _cell_length_c 24.468(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4958.5(12) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 210 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.5 _exptl_crystal_description Rectangular _exptl_crystal_colour Colourless _exptl_crystal_size_max .60 _exptl_crystal_size_mid .42 _exptl_crystal_size_min .32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method ? _exptl_crystal_F_000 2256 _exptl_absorpt_coefficient_mu 0.297 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 2689 _diffrn_reflns_av_R_equivalents 0.0345 _diffrn_reflns_av_sigmaI/netI 0.0480 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2194 _reflns_number_gt 1457 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2193 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_all 0.1086 _refine_ls_wR_factor_ref 0.0841 _refine_ls_goodness_of_fit_all 1.134 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.136 _refine_ls_restrained_S_obs 1.123 _refine_ls_shift/su_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.31729(9) 0.04306(8) 0.45674(11) 0.0295(8) Uani 1 d . . N1 N 0.4083(3) -0.0046(2) 0.6608(3) 0.019(3) Uani 1 d . . S2 S 0.73764(10) 0.20292(7) 0.82693(11) 0.0360(9) Uani 1 d . . F2 F 0.0870(2) 0.0470(2) 0.4550(2) 0.095(3) Uani 1 d . . C2 C 0.4207(3) 0.0472(2) 0.6252(3) 0.023(3) Uani 1 d . . H2A H 0.3780(3) 0.0461(2) 0.5918(3) 0.028 Uiso 1 calc R . O3 O 0.4965(2) 0.1037(2) 0.6366(2) 0.023(2) Uani 1 d . . F3 F 0.1626(4) -0.0328(3) 0.4010(4) 0.106(4) Uani 1 d . . O4 O 0.7900(3) 0.2032(3) 0.8809(3) 0.058(3) Uani 1 d . . C4 C 0.5125(3) 0.1524(2) 0.5958(3) 0.023(3) Uani 1 d . . H4A H 0.4773(3) 0.1441(2) 0.5611(3) 0.028 Uiso 1 calc R . N5 N 0.5762(3) 0.2106(2) 0.6042(3) 0.020(3) Uani 1 d . . F5 F 0.5333(2) 0.2385(2) 0.8697(2) 0.070(2) Uani 1 d . . C6A C 0.5989(3) 0.2629(3) 0.5570(3) 0.028(3) Uani 1 d . . H6AA H 0.6346(3) 0.3095(3) 0.5722(3) 0.033 Uiso 1 calc R . C6B C 0.6269(4) 0.2285(2) 0.6589(4) 0.022(4) Uani 1 d . . H6BA H 0.6023(4) 0.1881(2) 0.6848(4) 0.027 Uiso 1 calc R . C6D C 0.4761(5) -0.0095(3) 0.7128(5) 0.036(5) Uani 1 d . . H6DA H 0.5279(5) 0.0357(3) 0.7151(5) 0.043 Uiso 1 calc R . C6C C 0.3216(4) -0.0663(3) 0.6468(3) 0.028(3) Uani 1 d . . H6CA H 0.3222(4) -0.1033(3) 0.6774(3) 0.034 Uiso 1 calc R . C7C C 0.5763(5) 0.3019(3) 0.6800(4) 0.051(4) Uani 1 d . . H7CA H 0.4899(5) 0.2989(3) 0.6806(4) 0.077 Uiso 1 calc R . H7CB H 0.6009(5) 0.3428(3) 0.6560(4) 0.077 Uiso 1 calc R . H7CC H 0.6056(5) 0.3112(3) 0.7171(4) 0.077 Uiso 1 calc R . C7H C 0.3926(5) -0.0076(3) 0.7616(4) 0.039(5) Uani 1 d . . H7HA H 0.3445(5) 0.0379(3) 0.7600(4) 0.059 Uiso 1 calc R . H7HB H 0.4386(5) -0.0079(3) 0.7955(4) 0.059 Uiso 1 calc R . H7HC H 0.3409(5) -0.0515(3) 0.7606(4) 0.059 Uiso 1 calc R . C7A C 0.6880(5) 0.2288(3) 0.5181(4) 0.050(5) Uani 1 d . . H7AA H 0.7597(5) 0.2156(3) 0.5383(4) 0.075 Uiso 1 calc R . H7AB H 0.7075(5) 0.2650(3) 0.4895(4) 0.075 Uiso 1 calc R . H7AC H 0.6543(5) 0.1838(3) 0.5015(4) 0.075 Uiso 1 calc R . C7F C 0.1973(4) -0.0339(3) 0.6426(4) 0.047(4) Uani 1 d . . H7FA H 0.1772(4) -0.0086(3) 0.6769(4) 0.071 Uiso 1 calc R . H7FB H 0.1408(4) -0.0743(3) 0.6359(4) 0.071 Uiso 1 calc R . H7FC H 0.1942(4) 0.0020(3) 0.6124(4) 0.071 Uiso 1 calc R . C7E C 0.3591(4) -0.1062(3) 0.5956(4) 0.031(4) Uani 1 d . . H7EA H 0.4392(4) -0.1259(3) 0.6004(4) 0.046 Uiso 1 calc R . H7EB H 0.3579(4) -0.0712(3) 0.5648(4) 0.046 Uiso 1 calc R . H7EC H 0.3045(4) -0.1476(3) 0.5883(4) 0.046 Uiso 1 calc R . C7D C 0.7615(4) 0.2292(3) 0.6569(4) 0.055(4) Uani 1 d . . H7DA H 0.7900(4) 0.1811(3) 0.6431(4) 0.082 Uiso 1 calc R . H7DB H 0.7928(4) 0.2377(3) 0.6937(4) 0.082 Uiso 1 calc R . H7DC H 0.7881(4) 0.2693(3) 0.6326(4) 0.082 Uiso 1 calc R . C7B C 0.4857(4) 0.2846(3) 0.5282(4) 0.059(4) Uani 1 d . . H7BA H 0.4306(4) 0.3063(3) 0.5547(4) 0.089 Uiso 1 calc R . H7BB H 0.4499(4) 0.2402(3) 0.5116(4) 0.089 Uiso 1 calc R . H7BC H 0.5032(4) 0.3214(3) 0.4997(4) 0.089 Uiso 1 calc R . C7G C 0.5560(4) -0.0779(3) 0.7107(4) 0.051(4) Uani 1 d . . H7GA H 0.6068(4) -0.0750(3) 0.6783(4) 0.076 Uiso 1 calc R . H7GB H 0.5075(4) -0.1232(3) 0.7087(4) 0.076 Uiso 1 calc R . H7GC H 0.6052(4) -0.0796(3) 0.7436(4) 0.076 Uiso 1 calc R . O9 O 0.7375(3) 0.2744(2) 0.8006(3) 0.050(3) Uani 1 d . . O11 O 0.3146(3) 0.1001(2) 0.4150(3) 0.048(3) Uani 1 d . . O12 O 0.3971(3) -0.0181(2) 0.4469(2) 0.044(2) Uani 1 d . . O15 O 0.7713(3) 0.1410(2) 0.7935(3) 0.049(3) Uani 1 d . . F16 F 0.5627(3) 0.1232(2) 0.8653(3) 0.108(3) Uani 1 d . . F17 F 0.1584(3) -0.0548(2) 0.4868(3) 0.081(3) Uani 1 d . . F18 F 0.5225(3) 0.1811(3) 0.7936(3) 0.104(3) Uani 1 d . . C19 C 0.1729(4) -0.0010(4) 0.4503(6) 0.050(4) Uani 1 d . . C28 C 0.5830(5) 0.1851(3) 0.8403(5) 0.054(4) Uani 1 d . . O30 O 0.3176(3) 0.0710(2) 0.5122(3) 0.052(3) Uani 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0299(6) 0.0277(8) 0.031(3) -0.0024(11) 0.0021(6) 0.0049(4) N1 0.036(2) 0.017(2) 0.005(10) 0.002(3) 0.004(2) -0.0061(14) S2 0.0318(7) 0.0333(8) 0.043(3) -0.0003(10) -0.0028(7) 0.0087(5) F2 0.034(2) 0.060(2) 0.192(9) 0.030(3) 0.006(2) 0.0139(14) C2 0.025(2) 0.022(3) 0.022(10) -0.006(3) 0.002(2) -0.003(2) O3 0.035(2) 0.019(2) 0.015(7) 0.003(2) 0.002(2) -0.0065(11) F3 0.099(4) 0.106(4) 0.115(14) -0.031(5) -0.049(4) -0.024(3) O4 0.037(2) 0.115(4) 0.022(10) 0.009(4) -0.005(2) 0.020(2) C4 0.021(2) 0.022(3) 0.026(10) -0.003(3) 0.003(2) 0.0021(15) N5 0.025(2) 0.016(2) 0.018(9) -0.001(3) 0.004(2) 0.0007(13) F5 0.035(2) 0.063(2) 0.112(8) -0.041(3) 0.009(2) 0.0037(14) C6A 0.032(3) 0.021(3) 0.029(11) 0.002(4) 0.001(2) -0.008(2) C6B 0.033(3) 0.025(3) 0.010(13) 0.000(4) 0.001(3) -0.005(2) C6D 0.049(4) 0.026(3) 0.033(17) 0.003(5) -0.007(4) -0.009(2) C6C 0.042(3) 0.021(3) 0.021(12) 0.002(4) 0.000(3) -0.012(2) C7C 0.055(4) 0.041(3) 0.058(14) -0.017(4) -0.004(3) 0.005(2) C7H 0.068(4) 0.036(3) 0.014(17) 0.003(5) 0.003(4) 0.009(2) C7A 0.079(5) 0.053(4) 0.018(17) 0.008(5) 0.028(4) 0.007(3) C7F 0.039(3) 0.040(3) 0.063(13) -0.006(4) 0.007(3) -0.013(2) C7E 0.059(4) 0.023(3) 0.009(13) 0.000(4) -0.002(3) -0.009(2) C7D 0.029(3) 0.058(3) 0.076(13) 0.006(5) -0.011(3) 0.002(2) C7B 0.048(4) 0.063(4) 0.066(15) 0.034(5) -0.017(3) -0.007(2) C7G 0.041(3) 0.058(4) 0.053(13) 0.018(5) 0.007(3) 0.007(2) O9 0.066(3) 0.030(2) 0.055(10) 0.005(3) 0.007(2) 0.0089(15) O11 0.062(3) 0.043(2) 0.039(10) 0.023(3) 0.009(2) 0.003(2) O12 0.040(2) 0.039(2) 0.053(8) -0.005(3) 0.011(2) 0.0128(13) O15 0.064(3) 0.034(2) 0.049(9) -0.011(3) 0.015(2) 0.011(2) F16 0.093(3) 0.049(2) 0.180(11) 0.012(4) 0.077(3) -0.008(2) F17 0.053(2) 0.054(2) 0.136(10) 0.040(3) 0.009(2) -0.0073(14) F18 0.050(3) 0.168(5) 0.095(11) -0.053(5) -0.019(3) -0.016(2) C19 0.036(3) 0.045(4) 0.070(14) 0.004(6) -0.010(3) 0.002(2) C28 0.037(3) 0.041(4) 0.084(14) -0.021(5) 0.000(4) 0.000(2) O30 0.073(3) 0.045(3) 0.038(12) -0.016(4) -0.002(3) 0.011(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 O12 1.440(3) . ? S1 O11 1.444(5) . ? S1 O30 1.447(7) . ? S1 C19 1.822(6) . ? N1 C2 1.280(8) . ? N1 C6D 1.490(12) . ? N1 C6C 1.517(6) . ? S2 O15 1.429(5) . ? S2 O9 1.433(4) . ? S2 O4 1.448(7) . ? S2 C28 1.810(6) . ? F2 C19 1.303(6) . ? C2 O3 1.355(5) . ? O3 C4 1.337(7) . ? F3 C19 1.339(13) . ? C4 N5 1.282(5) . ? N5 C6B 1.491(11) . ? N5 C6A 1.510(9) . ? F5 C28 1.322(8) . ? C6A C7B 1.513(8) . ? C6A C7A 1.514(9) . ? C6B C7C 1.523(7) . ? C6B C7D 1.525(6) . ? C6D C7H 1.522(13) . ? C6D C7G 1.524(7) . ? C6C C7E 1.502(10) . ? C6C C7F 1.525(6) . ? F16 C28 1.286(8) . ? F17 C19 1.324(12) . ? F18 C28 1.335(12) . ? 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 O12 S1 O11 115.6(3) . . ? O12 S1 O30 114.7(3) . . ? O11 S1 O30 114.8(3) . . ? O12 S1 C19 102.7(3) . . ? O11 S1 C19 103.1(4) . . ? O30 S1 C19 103.4(4) . . ? C2 N1 C6D 124.5(4) . . ? C2 N1 C6C 116.5(6) . . ? C6D N1 C6C 118.9(6) . . ? O15 S2 O9 115.9(4) . . ? O15 S2 O4 114.6(3) . . ? O9 S2 O4 114.0(3) . . ? O15 S2 C28 103.0(3) . . ? O9 S2 C28 103.7(3) . . ? O4 S2 C28 103.4(4) . . ? N1 C2 O3 118.1(6) . . ? C4 O3 C2 114.8(5) . . ? N5 C4 O3 119.1(7) . . ? C4 N5 C6B 122.4(6) . . ? C4 N5 C6A 118.4(6) . . ? C6B N5 C6A 119.2(4) . . ? N5 C6A C7B 111.8(4) . . ? N5 C6A C7A 110.2(4) . . ? C7B C6A C7A 112.1(7) . . ? N5 C6B C7C 110.2(5) . . ? N5 C6B C7D 111.0(6) . . ? C7C C6B C7D 112.3(4) . . ? N1 C6D C7H 110.4(6) . . ? N1 C6D C7G 108.9(7) . . ? C7H C6D C7G 114.4(7) . . ? C7E C6C N1 110.6(5) . . ? C7E C6C C7F 112.7(6) . . ? N1 C6C C7F 109.6(4) . . ? F2 C19 F17 109.2(8) . . ? F2 C19 F3 107.1(8) . . ? F17 C19 F3 106.7(6) . . ? F2 C19 S1 112.2(4) . . ? F17 C19 S1 111.6(6) . . ? F3 C19 S1 109.9(7) . . ? F16 C28 F5 106.8(8) . . ? F16 C28 F18 105.6(6) . . ? F5 C28 F18 106.7(5) . . ? F16 C28 S2 114.2(4) . . ? F5 C28 S2 112.5(4) . . ? F18 C28 S2 110.6(8) . . ? _refine_diff_density_max 0.177 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.039 #===END data_meb3c _database_code_CSD 155808 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C12 H22 F6 N3 P' _chemical_formula_weight 353.30 _chemical_melting_point ? _chemical_compound_source ? 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' '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 12.0943(2) _cell_length_b 16.09920(10) _cell_length_c 16.45560(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3204.05(6) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 301 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.5 _exptl_crystal_description Rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max .66 _exptl_crystal_size_mid .45 _exptl_crystal_size_min .36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.465 _exptl_crystal_density_method ? _exptl_crystal_F_000 1472 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART Area Detector' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19842 _diffrn_reflns_av_R_equivalents 0.0402 _diffrn_reflns_av_sigmaI/netI 0.0290 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6988 _reflns_number_gt 6120 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995b)' _computing_cell_refinement 'SMART (Siemens, 1995b)' _computing_data_reduction 'SMART (Siemens, 1995b)' _computing_structure_solution 'SHELXTL (Siemens, 1995a)' _computing_structure_refinement 'SHELXTL (Siemens, 1995a)' _computing_molecular_graphics 'SHELXTL (Siemens, 1995a)' _computing_publication_material 'SHELXTL (Siemens, 1995a)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 2 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0488P)^2^+1.0694P] 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 noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.56(8) _refine_ls_number_reflns 6986 _refine_ls_number_parameters 394 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0398 _refine_ls_wR_factor_all 0.1088 _refine_ls_wR_factor_ref 0.1009 _refine_ls_goodness_of_fit_all 1.094 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.095 _refine_ls_restrained_S_obs 1.090 _refine_ls_shift/su_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P -0.18890(5) -0.08937(4) -0.22659(3) 0.02929(14) Uani 1 d . . P1A P -0.69733(5) -0.41164(4) -0.47767(4) 0.03040(15) Uani 1 d . . F1A F -0.7625(2) -0.49751(10) -0.48454(11) 0.0628(5) Uani 1 d . . F1 F -0.14141(13) -0.18132(9) -0.23341(11) 0.0522(4) Uani 1 d . . N1A N -0.6596(2) -0.20982(13) -0.24694(13) 0.0356(4) Uani 1 d . . N1 N -0.53967(15) -0.45179(11) -0.18084(12) 0.0288(4) Uani 1 d . . F2A F -0.81338(12) -0.36340(12) -0.47526(12) 0.0569(5) Uani 1 d . . F2 F -0.2375(2) 0.00221(9) -0.22016(11) 0.0613(5) Uani 1 d . . C2A C -0.5812(2) -0.15885(15) -0.2706(2) 0.0339(5) Uani 1 d . . H2AA H -0.5258(2) -0.14329(15) -0.2327(2) 0.041 Uiso 1 calc R . C2 C -0.5133(2) -0.42313(13) -0.10913(13) 0.0268(4) Uani 1 d . . H2A H -0.5535(2) -0.44183(13) -0.06303(13) 0.032 Uiso 1 calc R . F3A F -0.63560(14) -0.32513(10) -0.47139(12) 0.0558(5) Uani 1 d . . F3 F -0.17024(15) -0.09138(11) -0.13069(10) 0.0524(4) Uani 1 d . . N3A N -0.5762(2) -0.12827(13) -0.34511(12) 0.0348(4) Uani 1 d . . N3 N -0.43210(15) -0.36872(12) -0.09869(11) 0.0297(4) Uani 1 d . . F4A F -0.58229(15) -0.45951(12) -0.47968(13) 0.0660(5) Uani 1 d . . F4 F -0.31004(12) -0.12632(12) -0.21363(11) 0.0532(5) Uani 1 d . . C4A C -0.4941(2) -0.07483(15) -0.35733(15) 0.0325(5) Uani 1 d . . H4AA H -0.4474(2) -0.06105(15) -0.31291(15) 0.039 Uiso 1 calc R . C4 C -0.4194(2) -0.34396(13) -0.02211(13) 0.0274(4) Uani 1 d . . H4A H -0.4703(2) -0.36291(13) 0.01770(13) 0.033 Uiso 1 calc R . F5A F -0.69978(14) -0.41811(12) -0.38084(10) 0.0537(5) Uani 1 d . . F5 F -0.2094(2) -0.08719(12) -0.32233(10) 0.0618(5) Uani 1 d . . N5A N -0.4750(2) -0.04058(12) -0.42757(12) 0.0341(4) Uani 1 d . . N5 N -0.3396(2) -0.29471(12) 0.00022(11) 0.0292(4) Uani 1 d . . F6A F -0.6978(2) -0.40580(12) -0.57454(10) 0.0626(6) Uani 1 d . . F6 F -0.06744(14) -0.05293(11) -0.23865(14) 0.0657(5) Uani 1 d . . C6A' C -0.6695(2) -0.2361(2) -0.1625(2) 0.0409(6) Uani 1 d . . H6AA H -0.6023(2) -0.2197(2) -0.1321(2) 0.049 Uiso 1 calc R . H6AB H -0.6761(2) -0.2974(2) -0.1600(2) 0.049 Uiso 1 calc R . C6A C -0.3878(2) 0.0214(2) -0.4394(2) 0.0384(5) Uani 1 d . . H6AC H -0.3342(2) 0.0011(2) -0.4803(2) 0.046 Uiso 1 calc R . H6AD H -0.3477(2) 0.0303(2) -0.3877(2) 0.046 Uiso 1 calc R . C6' C -0.6242(2) -0.51680(14) -0.19125(14) 0.0330(5) Uani 1 d . . H6'A H -0.6811(2) -0.49778(14) -0.23033(14) 0.040 Uiso 1 calc R . H6'B H -0.6609(2) -0.52790(14) -0.13860(14) 0.040 Uiso 1 calc R . C6 C -0.3278(2) -0.26721(15) 0.08527(14) 0.0330(5) Uani 1 d . . H6A H -0.3896(2) -0.28954(15) 0.11809(14) 0.040 Uiso 1 calc R . H6B H -0.3309(2) -0.20582(15) 0.08779(14) 0.040 Uiso 1 calc R . C7A' C -0.7700(2) -0.1967(2) -0.12381(14) 0.0378(5) Uani 1 d . . H7AA H -0.7594(2) -0.1359(2) -0.12047(14) 0.045 Uiso 1 calc R . H7AB H -0.7792(2) -0.2183(2) -0.06788(14) 0.045 Uiso 1 calc R . C7A C -0.4382(2) 0.1028(2) -0.4679(2) 0.0409(6) Uani 1 d . . H7AC H -0.3785(2) 0.1431(2) -0.4797(2) 0.049 Uiso 1 calc R . H7AD H -0.4851(2) 0.1262(2) -0.4242(2) 0.049 Uiso 1 calc R . C7' C -0.5704(2) -0.5955(2) -0.2224(2) 0.0383(5) Uani 1 d . . H7'A H -0.6279(2) -0.6378(2) -0.2333(2) 0.046 Uiso 1 calc R . H7'B H -0.5198(2) -0.6179(2) -0.1805(2) 0.046 Uiso 1 calc R . C7 C -0.2186(2) -0.2973(2) 0.1200(2) 0.0402(6) Uani 1 d . . H7A H -0.2190(2) -0.3587(2) 0.1232(2) 0.048 Uiso 1 calc R . H7B H -0.2089(2) -0.2751(2) 0.1756(2) 0.048 Uiso 1 calc R . C8A' C -0.8729(2) -0.2156(2) -0.1730(2) 0.0391(5) Uani 1 d . . H8AA H -0.9362(2) -0.1844(2) -0.1500(2) 0.047 Uiso 1 calc R . H8AB H -0.8899(2) -0.2756(2) -0.1689(2) 0.047 Uiso 1 calc R . C8A C -0.5082(2) 0.0895(2) -0.5445(2) 0.0463(6) Uani 1 d . . H8AC H -0.5443(2) 0.1423(2) -0.5602(2) 0.056 Uiso 1 calc R . H8AD H -0.4602(2) 0.0715(2) -0.5899(2) 0.056 Uiso 1 calc R . C8' C -0.5057(2) -0.5779(2) -0.3003(2) 0.0422(6) Uani 1 d . . H8'A H -0.4664(2) -0.6289(2) -0.3176(2) 0.051 Uiso 1 calc R . H8'B H -0.5577(2) -0.5620(2) -0.3441(2) 0.051 Uiso 1 calc R . C8 C -0.1234(2) -0.2689(2) 0.0665(2) 0.0502(7) Uani 1 d . . H8A H -0.1181(2) -0.2075(2) 0.0682(2) 0.060 Uiso 1 calc R . H8B H -0.0532(2) -0.2919(2) 0.0876(2) 0.060 Uiso 1 calc R . C9A' C -0.8587(2) -0.1922(2) -0.2621(2) 0.0388(6) Uani 1 d . . H9AA H -0.9240(2) -0.2116(2) -0.2930(2) 0.047 Uiso 1 calc R . H9AB H -0.8552(2) -0.1310(2) -0.2669(2) 0.047 Uiso 1 calc R . C9A C -0.59585(15) 0.02347(14) -0.52817(13) 0.0488(7) Uani 1 d . . H9AC H -0.64806(15) 0.04416(14) -0.48649(13) 0.059 Uiso 1 calc R . H9AD H -0.63820(15) 0.01296(14) -0.57863(13) 0.059 Uiso 1 calc R . C9' C -0.42232(15) -0.50819(14) -0.28713(13) 0.0531(8) Uani 1 d R . H9'A H -0.36716(15) -0.52610(14) -0.24901(13) 0.064 Uiso 1 d R . H9'B H -0.38599(15) -0.49591(14) -0.33759(13) 0.064 Uiso 1 d R . C9 C -0.1399(2) -0.2971(2) -0.0207(2) 0.0457(7) Uani 1 d . . H9A H -0.1363(2) -0.3584(2) -0.0231(2) 0.055 Uiso 1 calc R . H9B H -0.0796(2) -0.2746(2) -0.0549(2) 0.055 Uiso 1 calc R . C10B C -0.7556(2) -0.2294(2) -0.2989(2) 0.0409(6) Uani 1 d . . H10A H -0.7642(2) -0.2904(2) -0.3035(2) 0.049 Uiso 1 calc R . H10B H -0.7439(2) -0.2066(2) -0.3540(2) 0.049 Uiso 1 calc R . C10A C -0.5445(2) -0.0568(2) -0.4992(2) 0.0452(6) Uani 1 d . . H10C H -0.6034(2) -0.0970(2) -0.4850(2) 0.054 Uiso 1 calc R . H10D H -0.4990(2) -0.0812(2) -0.5431(2) 0.054 Uiso 1 calc R . C10' C -0.4781(2) -0.4301(2) -0.25525(15) 0.0440(6) Uani 1 d . . H10E H -0.4219(2) -0.3872(2) -0.24300(15) 0.053 Uiso 1 calc R . H10F H -0.5294(2) -0.4077(2) -0.29669(15) 0.053 Uiso 1 calc R . C10 C -0.2507(2) -0.2680(2) -0.0542(2) 0.0410(6) Uani 1 d . . H10G H -0.2510(2) -0.2067(2) -0.0590(2) 0.049 Uiso 1 calc R . H10H H -0.2625(2) -0.2918(2) -0.1090(2) 0.049 Uiso 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 P1 0.0301(3) 0.0267(3) 0.0310(3) 0.0027(2) 0.0014(2) 0.0038(2) P1A 0.0311(3) 0.0278(3) 0.0323(4) 0.0000(2) -0.0016(2) -0.0008(2) F1A 0.0916(14) 0.0390(8) 0.0578(11) -0.0006(8) 0.0013(10) -0.0275(9) F1 0.0511(9) 0.0327(8) 0.0726(12) 0.0025(8) -0.0016(9) 0.0136(7) N1A 0.0295(10) 0.0353(10) 0.0421(12) 0.0007(9) 0.0006(9) 0.0021(8) N1 0.0271(8) 0.0306(9) 0.0288(10) -0.0003(8) -0.0019(7) -0.0035(7) F2A 0.0306(7) 0.0644(11) 0.0757(13) -0.0094(9) -0.0142(8) 0.0096(7) F2 0.0900(13) 0.0334(7) 0.0606(12) -0.0006(8) 0.0131(10) 0.0229(9) C2A 0.0289(11) 0.0353(12) 0.0375(13) -0.0042(10) 0.0000(9) 0.0053(9) C2 0.0239(9) 0.0305(11) 0.0260(10) 0.0000(9) 0.0000(8) 0.0042(8) F3A 0.0462(9) 0.0393(9) 0.0819(13) 0.0004(8) -0.0106(8) -0.0142(7) F3 0.0652(10) 0.0581(11) 0.0338(9) 0.0048(7) -0.0129(8) -0.0137(8) N3A 0.0326(10) 0.0378(11) 0.0341(11) -0.0068(9) 0.0038(8) 0.0017(8) N3 0.0315(9) 0.0318(9) 0.0258(9) 0.0012(8) -0.0024(7) -0.0039(8) F4A 0.0567(10) 0.0629(11) 0.0784(13) -0.0049(10) 0.0075(9) 0.0307(9) F4 0.0269(7) 0.0707(12) 0.0619(11) 0.0053(9) -0.0068(7) -0.0042(7) C4A 0.0262(11) 0.0341(11) 0.0371(13) -0.0062(10) 0.0019(9) 0.0067(9) C4 0.0257(10) 0.0292(10) 0.0275(11) 0.0024(9) -0.0017(8) 0.0008(8) F5A 0.0628(11) 0.0661(12) 0.0323(9) -0.0009(8) -0.0036(7) 0.0062(9) F5 0.0906(14) 0.0651(12) 0.0296(9) 0.0034(8) 0.0038(9) 0.0255(10) N5A 0.0310(10) 0.0401(11) 0.0313(10) -0.0046(9) 0.0004(8) 0.0011(8) N5 0.0317(9) 0.0301(9) 0.0258(9) -0.0006(8) -0.0004(7) -0.0034(8) F6A 0.094(2) 0.0627(12) 0.0316(9) 0.0052(8) 0.0027(9) -0.0075(10) F6 0.0441(9) 0.0586(10) 0.0943(15) 0.0242(11) 0.0152(9) -0.0120(8) C6A' 0.0365(13) 0.0362(12) 0.050(2) 0.0065(11) -0.0060(11) 0.0035(10) C6A 0.0249(10) 0.0495(14) 0.0409(14) 0.0008(12) 0.0014(10) -0.0006(10) C6' 0.0234(10) 0.0407(12) 0.0348(12) -0.0046(10) -0.0010(9) -0.0042(9) C6 0.0346(12) 0.0319(11) 0.0324(12) -0.0074(10) -0.0028(9) 0.0007(9) C7A' 0.0408(12) 0.0426(13) 0.0299(12) 0.0081(10) 0.0016(10) -0.0069(11) C7A 0.0368(12) 0.0444(14) 0.0416(14) -0.0020(11) 0.0019(11) -0.0033(11) C7' 0.0432(13) 0.0330(12) 0.0388(14) -0.0027(10) -0.0022(11) -0.0014(10) C7 0.0430(14) 0.0413(13) 0.0364(13) -0.0108(11) -0.0105(11) 0.0049(11) C8A' 0.0326(12) 0.0396(13) 0.0450(14) 0.0036(11) 0.0037(11) -0.0011(10) C8A 0.0369(13) 0.055(2) 0.047(2) 0.0100(13) -0.0012(11) 0.0060(12) C8' 0.0415(13) 0.0471(15) 0.0381(14) -0.0129(12) 0.0001(11) 0.0044(11) C8 0.0332(12) 0.059(2) 0.059(2) -0.022(2) -0.0066(13) -0.0015(12) C9A' 0.0311(12) 0.0398(13) 0.0456(14) 0.0024(11) -0.0064(10) -0.0026(10) C9A 0.0353(13) 0.073(2) 0.0380(14) 0.0034(14) -0.0071(11) -0.0043(13) C9' 0.0405(15) 0.082(2) 0.0372(14) -0.0161(14) 0.0090(11) -0.0146(14) C9 0.0361(13) 0.053(2) 0.048(2) -0.0132(13) 0.0087(11) -0.0124(12) C10B 0.0392(13) 0.0467(14) 0.0366(13) -0.0112(11) -0.0006(10) -0.0090(11) C10A 0.0469(14) 0.059(2) 0.0297(12) -0.0066(12) -0.0026(11) -0.0132(13) C10' 0.058(2) 0.0496(15) 0.0244(12) 0.0001(11) -0.0015(11) -0.0241(13) C10 0.0441(14) 0.0458(14) 0.0332(13) -0.0007(11) 0.0059(10) -0.0190(12) _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 F2 1.590(2) . ? P1 F1 1.5918(15) . ? P1 F6 1.594(2) . ? P1 F3 1.594(2) . ? P1 F5 1.595(2) . ? P1 F4 1.596(2) . ? P1A F3A 1.583(2) . ? P1A F4A 1.591(2) . ? P1A F1A 1.596(2) . ? P1A F6A 1.597(2) . ? P1A F5A 1.597(2) . ? P1A F2A 1.605(2) . ? N1A C2A 1.313(3) . ? N1A C6A' 1.458(3) . ? N1A C10B 1.476(3) . ? N1 C2 1.307(3) . ? N1 C6' 1.473(3) . ? N1 C10' 1.475(3) . ? C2A N3A 1.322(3) . ? C2 N3 1.327(3) . ? N3A C4A 1.329(3) . ? N3 C4 1.331(3) . ? C4A N5A 1.301(3) . ? C4 N5 1.302(3) . ? N5A C6A 1.464(3) . ? N5A C10A 1.471(3) . ? N5 C10 1.464(3) . ? N5 C6 1.475(3) . ? C6A' C7A' 1.511(4) . ? C6A C7A 1.519(4) . ? C6' C7' 1.513(3) . ? C6 C7 1.518(3) . ? C7A' C8A' 1.515(3) . ? C7A C8A 1.533(4) . ? C7' C8' 1.529(4) . ? C7 C8 1.520(4) . ? C8A' C9A' 1.523(4) . ? C8A C9A 1.525(3) . ? C8' C9' 1.524(3) . ? C8 C9 1.518(4) . ? C9A' C10B 1.510(4) . ? C9A C10A 1.511(4) . ? C9' C10' 1.520(4) . ? C9 C10 1.523(4) . ? 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 F2 P1 F1 179.44(11) . . ? F2 P1 F6 90.42(11) . . ? F1 P1 F6 90.05(9) . . ? F2 P1 F3 90.30(10) . . ? F1 P1 F3 89.99(10) . . ? F6 P1 F3 90.01(11) . . ? F2 P1 F5 89.32(10) . . ? F1 P1 F5 90.39(9) . . ? F6 P1 F5 90.69(12) . . ? F3 P1 F5 179.20(11) . . ? F2 P1 F4 89.87(11) . . ? F1 P1 F4 89.65(9) . . ? F6 P1 F4 179.37(11) . . ? F3 P1 F4 89.43(9) . . ? F5 P1 F4 89.86(10) . . ? F3A P1A F4A 90.87(10) . . ? F3A P1A F1A 178.46(11) . . ? F4A P1A F1A 90.63(12) . . ? F3A P1A F6A 90.87(10) . . ? F4A P1A F6A 90.63(11) . . ? F1A P1A F6A 88.77(10) . . ? F3A P1A F5A 90.06(10) . . ? F4A P1A F5A 90.31(11) . . ? F1A P1A F5A 90.29(10) . . ? F6A P1A F5A 178.68(11) . . ? F3A P1A F2A 89.15(9) . . ? F4A P1A F2A 179.77(11) . . ? F1A P1A F2A 89.35(11) . . ? F6A P1A F2A 89.60(11) . . ? F5A P1A F2A 89.46(10) . . ? C2A N1A C6A' 121.6(2) . . ? C2A N1A C10B 122.0(2) . . ? C6A' N1A C10B 115.1(2) . . ? C2 N1 C6' 121.7(2) . . ? C2 N1 C10' 122.9(2) . . ? C6' N1 C10' 114.9(2) . . ? N1A C2A N3A 122.8(2) . . ? N1 C2 N3 122.1(2) . . ? C2A N3A C4A 114.6(2) . . ? C2 N3 C4 113.9(2) . . ? N5A C4A N3A 122.8(2) . . ? N5 C4 N3 122.4(2) . . ? C4A N5A C6A 122.3(2) . . ? C4A N5A C10A 122.3(2) . . ? C6A N5A C10A 115.2(2) . . ? C4 N5 C10 123.4(2) . . ? C4 N5 C6 121.5(2) . . ? C10 N5 C6 115.0(2) . . ? N1A C6A' C7A' 110.2(2) . . ? N5A C6A C7A 109.9(2) . . ? N1 C6' C7' 109.6(2) . . ? N5 C6 C7 110.2(2) . . ? C6A' C7A' C8A' 110.6(2) . . ? C6A C7A C8A 110.8(2) . . ? C6' C7' C8' 110.4(2) . . ? C6 C7 C8 110.2(2) . . ? C7A' C8A' C9A' 111.9(2) . . ? C9A C8A C7A 109.7(2) . . ? C9' C8' C7' 110.8(2) . . ? C9 C8 C7 110.9(2) . . ? C10B C9A' C8A' 112.4(2) . . ? C10A C9A C8A 111.4(2) . . ? C10' C9' C8' 111.3(2) . . ? C8 C9 C10 111.5(2) . . ? N1A C10B C9A' 109.4(2) . . ? N5A C10A C9A 109.6(2) . . ? N1 C10' C9' 108.4(2) . . ? N5 C10 C9 109.5(2) . . ? _refine_diff_density_max 0.424 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.045