# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_alpha_bmim_PF6_100K _database_code_depnum_ccdc_archive 'CCDC 909171' _refine_special_details ; The Following ALERTS were generated by PLATON checkcif PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for P1 Noted, no action taken. PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? The one given is more meaningful. ; _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C8 H15 N2, P F6' _chemical_formula_sum 'C8 H15 F6 N2 P' _chemical_formula_weight 284.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab ' 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 9.3855(3) _cell_length_b 9.7769(3) _cell_length_c 26.7170(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2451.58(13) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9986 _cell_measurement_theta_min 4.8165 _cell_measurement_theta_max 71.7495 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 2.592 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SADABS V.2008/1 # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.2986 _exptl_absorpt_correction_T_max 0.7536 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'INCOATEC multilayer optics' _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method \w _diffrn_reflns_number 24529 _diffrn_reflns_av_R_equivalents 0.0505 _diffrn_reflns_av_sigmaI/netI 0.0270 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 72.18 _reflns_number_total 2380 _reflns_number_gt 2254 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'PLATON, XCIF, ENCIFER, SHELXLE' _computing_molecular_graphics MERCURY _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^)+(0.0513P)^2^+1.0815P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2380 _refine_ls_number_parameters 156 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0368 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.1000 _refine_ls_wR_factor_gt 0.0988 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 -0.00640(4) 0.84290(4) 0.108948(13) 0.02622(15) Uani 1 1 d . . . F1 F -0.07153(16) 0.92865(11) 0.06343(4) 0.0604(4) Uani 1 1 d . . . F2 F -0.10059(11) 0.92716(11) 0.14734(4) 0.0461(3) Uani 1 1 d . . . F4 F 0.11762(11) 0.95248(11) 0.11417(4) 0.0450(3) Uani 1 1 d . . . F3 F 0.06007(13) 0.75398(11) 0.15280(4) 0.0488(3) Uani 1 1 d . . . F5 F 0.08838(12) 0.75802(9) 0.06931(3) 0.0423(3) Uani 1 1 d . . . F6 F -0.12953(12) 0.73097(11) 0.10326(5) 0.0542(3) Uani 1 1 d . . . N1 N 0.00338(13) 0.86775(15) 0.38669(5) 0.0280(3) Uani 1 1 d . . . C2 C -0.07991(16) 0.95096(15) 0.41275(5) 0.0277(3) Uani 1 1 d . . . H2 H -0.1123 1.0382 0.4020 0.033 Uiso 1 1 calc R . . N3 N -0.11067(13) 0.89247(13) 0.45627(4) 0.0276(3) Uani 1 1 d . . . C4 C -0.04605(18) 0.76595(16) 0.45776(6) 0.0321(3) Uani 1 1 d . . . H4 H -0.0508 0.7017 0.4844 0.039 Uiso 1 1 calc R . . C5 C 0.02529(18) 0.75060(16) 0.41427(6) 0.0327(4) Uani 1 1 d . . . H5 H 0.0803 0.6735 0.4045 0.039 Uiso 1 1 calc R . . C6 C -0.20224(18) 0.95178(19) 0.49521(6) 0.0365(4) Uani 1 1 d . . . H6A H -0.1922 1.0516 0.4950 0.055 Uiso 1 1 calc R . . H6B H -0.1739 0.9160 0.5280 0.055 Uiso 1 1 calc R . . H6C H -0.3017 0.9273 0.4886 0.055 Uiso 1 1 calc R . . C7 C 0.05566(19) 0.89490(17) 0.33562(6) 0.0357(4) Uani 1 1 d . . . H7A H 0.1425 0.8400 0.3294 0.043 Uiso 1 1 calc R . . H7B H 0.0815 0.9927 0.3326 0.043 Uiso 1 1 calc R . . C8 C -0.05597(19) 0.85989(17) 0.29656(6) 0.0339(4) Uani 1 1 d . . . H8A H -0.0199 0.8878 0.2633 0.041 Uiso 1 1 calc R . . H8B H -0.1428 0.9141 0.3035 0.041 Uiso 1 1 calc R . . C9 C -0.09637(17) 0.70967(17) 0.29449(6) 0.0333(4) Uani 1 1 d . . . H9A H -0.1385 0.6825 0.3270 0.040 Uiso 1 1 calc R . . H9B H -0.0093 0.6543 0.2893 0.040 Uiso 1 1 calc R . . C10 C -0.2021(2) 0.6790(2) 0.25286(6) 0.0413(4) Uani 1 1 d . . . H10A H -0.2910 0.7287 0.2591 0.062 Uiso 1 1 calc R . . H10B H -0.2214 0.5805 0.2519 0.062 Uiso 1 1 calc R . . H10C H -0.1620 0.7081 0.2207 0.062 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 P1 0.0310(3) 0.0264(3) 0.0213(2) 0.00025(13) -0.00114(13) -0.00118(15) F1 0.1029(10) 0.0387(6) 0.0395(6) -0.0024(4) -0.0290(6) 0.0229(6) F2 0.0419(6) 0.0458(6) 0.0507(6) -0.0147(5) 0.0153(5) -0.0042(5) F4 0.0406(6) 0.0389(6) 0.0554(6) -0.0093(4) 0.0119(5) -0.0117(4) F3 0.0649(8) 0.0523(7) 0.0292(5) 0.0107(4) -0.0069(5) 0.0059(5) F5 0.0653(7) 0.0278(5) 0.0338(5) 0.0021(4) 0.0174(5) 0.0040(4) F6 0.0401(6) 0.0410(6) 0.0814(8) -0.0159(5) -0.0039(5) -0.0101(5) N1 0.0307(7) 0.0269(7) 0.0263(7) 0.0012(5) -0.0002(5) -0.0025(5) C2 0.0318(8) 0.0236(7) 0.0278(7) -0.0010(5) -0.0025(6) -0.0023(6) N3 0.0285(7) 0.0301(7) 0.0242(6) -0.0024(5) -0.0020(5) -0.0032(5) C4 0.0364(8) 0.0308(8) 0.0291(7) 0.0064(6) -0.0053(6) -0.0008(7) C5 0.0367(8) 0.0264(8) 0.0349(8) 0.0032(6) -0.0030(7) 0.0030(6) C6 0.0365(9) 0.0462(10) 0.0269(7) -0.0096(6) 0.0019(6) -0.0038(7) C7 0.0423(9) 0.0345(9) 0.0303(8) 0.0015(6) 0.0085(7) -0.0067(7) C8 0.0419(9) 0.0353(9) 0.0245(7) 0.0081(6) 0.0043(7) 0.0034(7) C9 0.0336(8) 0.0381(9) 0.0281(7) 0.0077(6) 0.0018(6) -0.0018(7) C10 0.0422(10) 0.0572(11) 0.0243(7) 0.0040(7) 0.0020(6) -0.0068(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 P1 F2 1.5849(10) . ? P1 F3 1.5867(10) . ? P1 F4 1.5881(10) . ? P1 F1 1.5986(10) . ? P1 F6 1.5989(11) . ? P1 F5 1.6128(10) . ? N1 C2 1.326(2) . ? N1 C5 1.377(2) . ? N1 C7 1.4741(19) . ? C2 N3 1.3274(19) . ? C2 H2 0.9500 . ? N3 C4 1.378(2) . ? N3 C6 1.4688(19) . ? C4 C5 1.349(2) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.518(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.518(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.520(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 F3 91.50(6) . . ? F2 P1 F4 90.08(6) . . ? F3 P1 F4 90.95(6) . . ? F2 P1 F1 90.37(7) . . ? F3 P1 F1 178.04(6) . . ? F4 P1 F1 89.61(7) . . ? F2 P1 F6 90.81(6) . . ? F3 P1 F6 88.81(7) . . ? F4 P1 F6 179.09(6) . . ? F1 P1 F6 90.59(7) . . ? F2 P1 F5 179.29(6) . . ? F3 P1 F5 89.20(6) . . ? F4 P1 F5 90.03(6) . . ? F1 P1 F5 88.93(6) . . ? F6 P1 F5 89.09(6) . . ? C2 N1 C5 108.51(13) . . ? C2 N1 C7 124.89(14) . . ? C5 N1 C7 126.52(14) . . ? N1 C2 N3 108.90(13) . . ? N1 C2 H2 125.6 . . ? N3 C2 H2 125.6 . . ? C2 N3 C4 108.44(13) . . ? C2 N3 C6 125.28(14) . . ? C4 N3 C6 126.25(13) . . ? C5 C4 N3 107.05(13) . . ? C5 C4 H4 126.5 . . ? N3 C4 H4 126.5 . . ? C4 C5 N1 107.10(14) . . ? C4 C5 H5 126.5 . . ? N1 C5 H5 126.5 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8 111.47(13) . . ? N1 C7 H7A 109.3 . . ? C8 C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? C7 C8 C9 114.56(13) . . ? C7 C8 H8A 108.6 . . ? C9 C8 H8A 108.6 . . ? C7 C8 H8B 108.6 . . ? C9 C8 H8B 108.6 . . ? H8A C8 H8B 107.6 . . ? C8 C9 C10 112.36(14) . . ? C8 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? C8 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.9 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? 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 C5 N1 C2 N3 0.84(17) . . . . ? C7 N1 C2 N3 177.64(14) . . . . ? N1 C2 N3 C4 -0.88(17) . . . . ? N1 C2 N3 C6 -178.99(13) . . . . ? C2 N3 C4 C5 0.57(18) . . . . ? C6 N3 C4 C5 178.65(14) . . . . ? N3 C4 C5 N1 -0.05(18) . . . . ? C2 N1 C5 C4 -0.48(18) . . . . ? C7 N1 C5 C4 -177.21(15) . . . . ? C2 N1 C7 C8 -81.19(19) . . . . ? C5 N1 C7 C8 95.02(19) . . . . ? N1 C7 C8 C9 -63.65(19) . . . . ? C7 C8 C9 C10 -176.76(14) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 72.18 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.332 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.049 data_alpha_bmim_PF6_193K _database_code_depnum_ccdc_archive 'CCDC 909172' _refine_special_details ; The Following ALERTS were generated by PLATON checkcif PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C10A This value is acceptable for a terminal methyl carbon - we were not able to refine a split model for this atom. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for P1 Noted, no action taken. PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? The one given is more meaningful. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.971 Diffraction resolution was partially compromised by the presence of disorder. Resolution and completeness are shown below: #=============================================================================Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #=============================================================================Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 50.43 0.500 0.999 1315 1314 1 57.99 0.550 0.998 1749 1745 4 67.68 0.600 0.989 2276 2252 24 #----------------------------------------------------------- ACTA Min. Res. --- 72.78 0.620 0.976 2487 2427 60 ; _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C8 H15 N2, P F6' _chemical_formula_sum 'C8 H15 F6 N2 P' _chemical_formula_weight 284.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab ' 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 9.4924(5) _cell_length_b 9.8406(5) _cell_length_c 26.8817(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2511.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9895 _cell_measurement_theta_min 3.288 _cell_measurement_theta_max 72.2375 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.8 _exptl_crystal_size_mid 0.6 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 2.531 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SADABS V.2008/1 # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.2599 _exptl_absorpt_correction_T_max 0.7536 _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'INCOATEC multilayer optics' _diffrn_measurement_device_type 'Bruker SMART 6000' _diffrn_measurement_method \w _diffrn_reflns_number 28075 _diffrn_reflns_av_R_equivalents 0.0652 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 72.78 _reflns_number_total 2427 _reflns_number_gt 2054 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'PLATON, XCIF, ENCIFER, SHELXLE' _computing_molecular_graphics MERCURY _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^)+(0.0890P)^2^+0.5459P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2427 _refine_ls_number_parameters 229 _refine_ls_number_restraints 255 _refine_ls_R_factor_all 0.0555 _refine_ls_R_factor_gt 0.0482 _refine_ls_wR_factor_ref 0.1551 _refine_ls_wR_factor_gt 0.1463 _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_restrained_S_all 1.150 _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 -0.01279(7) 0.84377(6) 0.10846(2) 0.0549(3) Uani 1 1 d D . . F1 F -0.0954(16) 0.9180(10) 0.0660(3) 0.138(5) Uani 0.42(2) 1 d PDU A 1 F3 F 0.0685(13) 0.7655(10) 0.1514(3) 0.110(3) Uani 0.42(2) 1 d PDU A 1 F2 F -0.0994(11) 0.9273(9) 0.1483(4) 0.096(3) Uani 0.42(2) 1 d PDU A 1 F5 F 0.0721(11) 0.7580(9) 0.0689(3) 0.083(3) Uani 0.42(2) 1 d PDU A 1 F4 F 0.1028(10) 0.9575(8) 0.1085(5) 0.082(3) Uani 0.42(2) 1 d PDU A 1 F6 F -0.1280(8) 0.7265(8) 0.1102(5) 0.093(3) Uani 0.42(2) 1 d PDU A 1 F11 F -0.0483(12) 0.9333(6) 0.06050(17) 0.096(2) Uani 0.58(2) 1 d PDU A 2 F31 F 0.0297(11) 0.7495(7) 0.15253(16) 0.097(2) Uani 0.58(2) 1 d PDU A 2 F21 F -0.1193(9) 0.9276(8) 0.1397(3) 0.120(3) Uani 0.58(2) 1 d PDU A 2 F51 F 0.0966(9) 0.7603(6) 0.0745(2) 0.0835(19) Uani 0.58(2) 1 d PDU A 2 F41 F 0.1079(7) 0.9481(7) 0.1215(4) 0.0808(18) Uani 0.58(2) 1 d PDU A 2 F61 F -0.1308(7) 0.7391(7) 0.0930(5) 0.119(3) Uani 0.58(2) 1 d PDU A 2 N1 N -0.0023(2) 0.8705(2) 0.38611(7) 0.0570(5) Uani 1 1 d . B . C2 C -0.0870(3) 0.9517(2) 0.41142(8) 0.0574(5) Uani 1 1 d . . . H2 H -0.1226 1.0364 0.4000 0.069 Uiso 1 1 calc R . . N3 N -0.11427(19) 0.89619(19) 0.45518(6) 0.0551(5) Uani 1 1 d . . . C4 C -0.0458(3) 0.7742(2) 0.45772(8) 0.0624(6) Uani 1 1 d . . . H4 H -0.0475 0.7123 0.4848 0.075 Uiso 1 1 calc R . . C5 C 0.0245(3) 0.7582(3) 0.41471(9) 0.0643(6) Uani 1 1 d . . . H5 H 0.0819 0.6830 0.4058 0.077 Uiso 1 1 calc R . . C6 C -0.2056(3) 0.9545(3) 0.49375(9) 0.0751(7) Uani 1 1 d . . . H6A H -0.2039 1.0538 0.4913 0.113 Uiso 1 1 calc R . . H6B H -0.1717 0.9266 0.5266 0.113 Uiso 1 1 calc R . . H6C H -0.3023 0.9219 0.4890 0.113 Uiso 1 1 calc R . . C7 C 0.0485(3) 0.8952(3) 0.33509(9) 0.0745(7) Uani 1 1 d D . . H7A H 0.1357 0.8423 0.3293 0.089 Uiso 0.750(8) 1 calc PR B 1 H7B H 0.0713 0.9927 0.3311 0.089 Uiso 0.750(8) 1 calc PR B 1 H7C H 0.1527 0.8978 0.3354 0.089 Uiso 0.250(8) 1 calc PR B 2 H7D H 0.0146 0.9853 0.3239 0.089 Uiso 0.250(8) 1 calc PR B 2 C8A C -0.0603(5) 0.8552(4) 0.29727(11) 0.0669(12) Uani 0.750(8) 1 d PD B 1 H8A H -0.0256 0.8816 0.2639 0.080 Uiso 0.750(8) 1 calc PR B 1 H8B H -0.1471 0.9080 0.3038 0.080 Uiso 0.750(8) 1 calc PR B 1 C9A C -0.0983(5) 0.7067(4) 0.29605(13) 0.0676(12) Uani 0.750(8) 1 d PD B 1 H9A H -0.0106 0.6535 0.2919 0.081 Uiso 0.750(8) 1 calc PR B 1 H9B H -0.1391 0.6818 0.3287 0.081 Uiso 0.750(8) 1 calc PR B 1 C8B C 0.0010(11) 0.7898(14) 0.2986(4) 0.074(4) Uani 0.250(8) 1 d PD B 2 H8C H 0.0482 0.7030 0.3069 0.089 Uiso 0.250(8) 1 calc PR B 2 H8D H 0.0336 0.8172 0.2651 0.089 Uiso 0.250(8) 1 calc PR B 2 C9B C -0.1561(11) 0.7647(15) 0.2963(4) 0.072(4) Uani 0.250(8) 1 d PD B 2 H9C H -0.1883 0.7302 0.3290 0.087 Uiso 0.250(8) 1 calc PR B 2 H9D H -0.2046 0.8522 0.2901 0.087 Uiso 0.250(8) 1 calc PR B 2 C10 C -0.1987(4) 0.6652(4) 0.25663(10) 0.1015(12) Uani 1 1 d D . . H10A H -0.2158 0.5672 0.2589 0.152 Uiso 0.750(8) 1 calc PR B 1 H10B H -0.1589 0.6869 0.2239 0.152 Uiso 0.750(8) 1 calc PR B 1 H10C H -0.2878 0.7141 0.2610 0.152 Uiso 0.750(8) 1 calc PR B 1 H10D H -0.2069 0.5742 0.2712 0.152 Uiso 0.250(8) 1 calc PR B 2 H10E H -0.1273 0.6641 0.2303 0.152 Uiso 0.250(8) 1 calc PR B 2 H10F H -0.2897 0.6923 0.2425 0.152 Uiso 0.250(8) 1 calc PR B 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 0.0559(4) 0.0540(4) 0.0547(4) 0.0004(2) -0.0013(2) -0.0028(2) F1 0.171(9) 0.110(6) 0.134(7) 0.021(4) -0.087(6) 0.041(5) F3 0.110(6) 0.125(6) 0.095(5) 0.035(4) -0.053(4) -0.008(4) F2 0.087(5) 0.104(6) 0.098(4) -0.045(4) 0.031(4) -0.025(4) F5 0.128(6) 0.075(5) 0.045(3) 0.000(2) 0.016(3) 0.008(4) F4 0.088(5) 0.067(3) 0.089(5) -0.008(3) 0.029(3) -0.021(3) F6 0.086(4) 0.063(3) 0.129(6) -0.010(3) -0.003(3) -0.013(3) F11 0.142(5) 0.071(3) 0.074(2) -0.0041(18) -0.031(2) 0.029(3) F31 0.142(5) 0.093(3) 0.056(2) 0.0226(19) 0.011(2) -0.017(3) F21 0.086(4) 0.109(5) 0.166(6) -0.045(4) 0.055(4) -0.002(3) F51 0.092(3) 0.047(3) 0.112(5) 0.009(2) 0.037(3) 0.011(2) F41 0.075(3) 0.088(3) 0.079(3) -0.0072(19) -0.004(2) -0.026(2) F61 0.080(3) 0.118(5) 0.158(6) -0.041(4) -0.007(3) -0.042(3) N1 0.0549(13) 0.0548(11) 0.0614(11) 0.0023(8) -0.0002(7) -0.0073(8) C2 0.0608(14) 0.0438(11) 0.0676(12) -0.0007(9) -0.0054(10) -0.0063(9) N3 0.0512(11) 0.0563(11) 0.0578(9) -0.0065(7) -0.0060(7) -0.0071(8) C4 0.0670(15) 0.0596(14) 0.0605(11) 0.0076(9) -0.0100(10) -0.0007(11) C5 0.0656(15) 0.0572(14) 0.0702(13) 0.0027(11) -0.0049(11) 0.0102(11) C6 0.0658(16) 0.0901(19) 0.0695(13) -0.0241(12) 0.0016(11) -0.0069(14) C7 0.0756(17) 0.0791(18) 0.0687(14) 0.0058(12) 0.0137(13) -0.0187(14) C8A 0.075(3) 0.071(2) 0.0551(16) 0.0148(14) 0.0063(16) 0.001(2) C9A 0.065(3) 0.075(3) 0.0632(18) 0.0129(17) 0.0035(17) -0.009(2) C8B 0.073(9) 0.088(10) 0.061(6) 0.010(5) 0.014(5) 0.013(7) C9B 0.068(9) 0.082(9) 0.067(6) -0.007(5) 0.003(5) 0.007(7) C10 0.115(3) 0.128(3) 0.0617(14) -0.0088(15) 0.0097(15) -0.030(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 P1 F21 1.552(4) . ? P1 F31 1.558(4) . ? P1 F1 1.566(4) . ? P1 F4 1.567(4) . ? P1 F61 1.578(4) . ? P1 F41 1.578(4) . ? P1 F5 1.579(4) . ? P1 F2 1.580(4) . ? P1 F3 1.588(4) . ? P1 F6 1.591(4) . ? P1 F11 1.597(4) . ? P1 F51 1.609(4) . ? N1 C2 1.322(3) . ? N1 C5 1.370(3) . ? N1 C7 1.474(3) . ? C2 N3 1.323(3) . ? C2 H2 0.9500 . ? N3 C4 1.367(3) . ? N3 C6 1.468(3) . ? C4 C5 1.344(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8B 1.496(9) . ? C7 C8A 1.502(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 H7C 0.9900 . ? C7 H7D 0.9900 . ? C8A C9A 1.506(5) . ? C8A H8A 0.9900 . ? C8A H8B 0.9900 . ? C9A C10 1.482(5) . ? C9A H9A 0.9900 . ? C9A H9B 0.9900 . ? C8B C9B 1.514(9) . ? C8B H8C 0.9900 . ? C8B H8D 0.9900 . ? C9B C10 1.503(8) . ? C9B H9C 0.9900 . ? C9B H9D 0.9900 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C10 H10D 0.9800 . ? C10 H10E 0.9800 . ? C10 H10F 0.9800 . ? 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 F4 91.0(3) . . ? F21 P1 F61 91.5(3) . . ? F31 P1 F61 89.8(3) . . ? F21 P1 F41 90.4(3) . . ? F31 P1 F41 91.7(3) . . ? F61 P1 F41 177.5(3) . . ? F1 P1 F5 90.8(3) . . ? F4 P1 F5 91.4(3) . . ? F1 P1 F2 89.5(3) . . ? F4 P1 F2 89.6(3) . . ? F5 P1 F2 179.0(4) . . ? F1 P1 F3 178.6(4) . . ? F4 P1 F3 90.4(3) . . ? F5 P1 F3 89.0(3) . . ? F2 P1 F3 90.8(3) . . ? F1 P1 F6 90.9(3) . . ? F4 P1 F6 178.1(4) . . ? F5 P1 F6 89.0(3) . . ? F2 P1 F6 90.0(3) . . ? F3 P1 F6 87.8(3) . . ? F21 P1 F11 90.4(3) . . ? F31 P1 F11 175.4(3) . . ? F61 P1 F11 89.8(3) . . ? F41 P1 F11 88.5(3) . . ? F21 P1 F51 178.0(3) . . ? F31 P1 F51 87.8(2) . . ? F61 P1 F51 88.6(3) . . ? F41 P1 F51 89.4(3) . . ? F11 P1 F51 87.6(2) . . ? C2 N1 C5 108.2(2) . . ? C2 N1 C7 125.3(2) . . ? C5 N1 C7 126.5(2) . . ? N1 C2 N3 109.1(2) . . ? N1 C2 H2 125.5 . . ? N3 C2 H2 125.5 . . ? C2 N3 C4 108.30(19) . . ? C2 N3 C6 125.6(2) . . ? C4 N3 C6 126.1(2) . . ? C5 C4 N3 107.2(2) . . ? C5 C4 H4 126.4 . . ? N3 C4 H4 126.4 . . ? C4 C5 N1 107.2(2) . . ? C4 C5 H5 126.4 . . ? N1 C5 H5 126.4 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8B 113.4(5) . . ? N1 C7 C8A 111.2(2) . . ? N1 C7 H7A 109.4 . . ? C8A C7 H7A 109.4 . . ? N1 C7 H7B 109.4 . . ? C8A C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N1 C7 H7C 108.9 . . ? C8B C7 H7C 108.9 . . ? N1 C7 H7D 108.9 . . ? C8B C7 H7D 108.9 . . ? H7C C7 H7D 107.7 . . ? C7 C8A C9A 115.7(3) . . ? C7 C8A H8A 108.4 . . ? C9A C8A H8A 108.4 . . ? C7 C8A H8B 108.4 . . ? C9A C8A H8B 108.4 . . ? H8A C8A H8B 107.4 . . ? C10 C9A C8A 115.9(4) . . ? C10 C9A H9A 108.3 . . ? C8A C9A H9A 108.3 . . ? C10 C9A H9B 108.3 . . ? C8A C9A H9B 108.3 . . ? H9A C9A H9B 107.4 . . ? C7 C8B C9B 115.9(8) . . ? C7 C8B H8C 108.3 . . ? C9B C8B H8C 108.3 . . ? C7 C8B H8D 108.3 . . ? C9B C8B H8D 108.3 . . ? H8C C8B H8D 107.4 . . ? C10 C9B C8B 113.6(8) . . ? C10 C9B H9C 108.8 . . ? C8B C9B H9C 108.8 . . ? C10 C9B H9D 108.8 . . ? C8B C9B H9D 108.8 . . ? H9C C9B H9D 107.7 . . ? C9A C10 H10A 109.5 . . ? C9A C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9A C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9B C10 H10D 109.5 . . ? H10C C10 H10D 109.4 . . ? C9B C10 H10E 109.5 . . ? H10D C10 H10E 109.5 . . ? C9B C10 H10F 109.5 . . ? H10D C10 H10F 109.5 . . ? H10E C10 H10F 109.5 . . ? 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 C5 N1 C2 N3 0.5(3) . . . . ? C7 N1 C2 N3 178.1(2) . . . . ? N1 C2 N3 C4 -0.7(2) . . . . ? N1 C2 N3 C6 -179.2(2) . . . . ? C2 N3 C4 C5 0.6(3) . . . . ? C6 N3 C4 C5 179.1(2) . . . . ? N3 C4 C5 N1 -0.3(3) . . . . ? C2 N1 C5 C4 -0.2(3) . . . . ? C7 N1 C5 C4 -177.7(2) . . . . ? C2 N1 C7 C8B -117.3(6) . . . . ? C5 N1 C7 C8B 59.8(7) . . . . ? C2 N1 C7 C8A -80.9(3) . . . . ? C5 N1 C7 C8A 96.2(4) . . . . ? N1 C7 C8A C9A -63.5(5) . . . . ? C8B C7 C8A C9A 37.2(8) . . . . ? C7 C8A C9A C10 -176.2(3) . . . . ? N1 C7 C8B C9B 54.1(14) . . . . ? C8A C7 C8B C9B -39.4(9) . . . . ? C7 C8B C9B C10 176.0(8) . . . . ? C8A C9A C10 C9B -42.9(10) . . . . ? C8B C9B C10 C9A 39.1(8) . . . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 72.78 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.271 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.052 data_beta_bmim_PF6_193K _database_code_depnum_ccdc_archive 'CCDC 909173' _refine_special_details ; The program TWINABS was used to generate a merged reflection file in the SHELXL HKLF5 format. From TWINABS: 6045 data ( 2320 unique ) involve domain 1 only, mean I/sigma 8.3 5985 data ( 2317 unique ) involve domain 2 only, mean I/sigma 7.1 7023 data ( 2163 unique ) involve 2 domains, mean I/sigma 13.6 The quoted R~int~ value (0.05) comes from scaling all single and composite reflections involving domain 1. For the generation of an HKLF5 file, all observations containing domain 1 were chosen. Single reflections that also occur in composites were omitted for merging. The Following ALERTS were generated by PLATON checkcif THETM01_ALERT_3_B The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5574 PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.978 The crystal was grown in situ in a capillary and is twinned as well as disordered. Twinning and disorder are characteristic features of this crystalline phase. The diffraction quality is not ideal and data could only be reliably integrated to the given resolution. Data to higher resolution has I/sigma(I) < 1.0. PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 1 Methyl carbon atom C10 is split over two positions and ADPs could not be modelled satisfactorily. PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for P1 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C9 PLAT084_ALERT_2_C High wR2 Value ................................. 0.28 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for P11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds ............... 0.0136 Ang RFACR01_ALERT_3_C The value of the weighted R factor is > 0.25 Weighted R factor given 0.275 Noted, no action taken. The structure is twinned and disordered. The disorder of the side chain could not be resolved beyond a split model for the terminal methyl group. PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? The one given is more meaningful. ; _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C8 H15 N2, P F6' _chemical_formula_sum 'C8 H15 F6 N2 P' _chemical_formula_weight 284.19 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.3869(8) _cell_length_b 9.5879(8) _cell_length_c 14.4964(12) _cell_angle_alpha 98.492(5) _cell_angle_beta 98.354(6) _cell_angle_gamma 101.089(6) _cell_volume 1245.85(18) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 5141 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 22.23 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.515 _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_process_details 'based on symmetry-related measuraments' # TWINABS V.2008/2 # The following data are from Twinabs: _exptl_absorpt_correction_T_min 0.50 _exptl_absorpt_correction_T_max 0.74 _exptl_special_details ; crystal grown in situ in a capillary ; _diffrn_ambient_temperature 193(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 'Bruker AXS APEX II' _diffrn_measurement_device_type Area _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_number 18072 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 23.34 _reflns_number_total 3544 _reflns_number_gt 2711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008), SHELXLE' _computing_publication_material 'PLATON, XCIF, ENCIFER, SHELXLE' _computing_molecular_graphics MERCURY _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^)+(0.1888P)^2^+1.0379P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3543 _refine_ls_number_parameters 349 _refine_ls_number_restraints 618 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0846 _refine_ls_wR_factor_ref 0.2750 _refine_ls_wR_factor_gt 0.2440 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.231 _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 0.0234(2) -0.0321(2) 0.25158(15) 0.0530(7) Uani 1 1 d D . . F101 F -0.1089(17) -0.1698(17) 0.2395(12) 0.101(5) Uani 0.53(2) 1 d PDU A 1 F103 F 0.1569(16) 0.0987(15) 0.2694(11) 0.101(5) Uani 0.53(2) 1 d PDU A 1 F102 F 0.024(2) -0.024(2) 0.3607(6) 0.135(6) Uani 0.53(2) 1 d PDU A 1 F105 F 0.015(2) -0.043(2) 0.1438(6) 0.135(6) Uani 0.53(2) 1 d PDU A 1 F104 F -0.0932(16) 0.0654(16) 0.2509(18) 0.119(6) Uani 0.53(2) 1 d PDU A 1 F106 F 0.1321(16) -0.1350(17) 0.2539(19) 0.119(6) Uani 0.53(2) 1 d PDU A 1 F111 F -0.1019(18) -0.1564(15) 0.2676(17) 0.105(6) Uani 0.47(2) 1 d PDU A 2 F113 F 0.1499(17) 0.0892(14) 0.2318(17) 0.105(6) Uani 0.47(2) 1 d PDU A 2 F112 F 0.122(3) -0.0515(19) 0.3436(12) 0.145(8) Uani 0.47(2) 1 d PDU A 2 F115 F -0.072(3) -0.023(2) 0.1565(11) 0.145(8) Uani 0.47(2) 1 d PDU A 2 F114 F -0.037(2) 0.0856(16) 0.3075(13) 0.109(7) Uani 0.47(2) 1 d PDU A 2 F116 F 0.090(2) -0.1514(16) 0.1947(14) 0.109(7) Uani 0.47(2) 1 d PDU A 2 P11 P 0.5893(2) 0.3653(2) 0.24907(16) 0.0549(7) Uani 1 1 d D . . F201 F 0.587(2) 0.2425(15) 0.3163(11) 0.098(5) Uani 0.51(2) 1 d PDU B 1 F203 F 0.592(2) 0.4751(16) 0.1825(11) 0.098(5) Uani 0.51(2) 1 d PDU B 1 F202 F 0.5132(16) 0.446(2) 0.3245(13) 0.106(5) Uani 0.51(2) 1 d PDU B 1 F205 F 0.672(2) 0.2722(18) 0.1853(13) 0.106(5) Uani 0.51(2) 1 d PDU B 1 F204 F 0.7376(13) 0.4592(17) 0.3125(12) 0.080(4) Uani 0.51(2) 1 d PDU B 1 F206 F 0.4331(12) 0.2779(16) 0.1946(12) 0.080(4) Uani 0.51(2) 1 d PDU B 1 F211 F 0.656(2) 0.2355(15) 0.2049(12) 0.085(4) Uani 0.49(2) 1 d PDU B 2 F213 F 0.5136(15) 0.4948(14) 0.2796(12) 0.085(4) Uani 0.49(2) 1 d PDU B 2 F212 F 0.5272(19) 0.276(2) 0.3209(10) 0.093(4) Uani 0.49(2) 1 d PDU B 2 F215 F 0.6550(19) 0.4567(18) 0.1749(10) 0.093(4) Uani 0.49(2) 1 d PDU B 2 F214 F 0.7392(13) 0.4215(18) 0.3211(9) 0.071(4) Uani 0.49(2) 1 d PDU B 2 F216 F 0.4510(13) 0.2947(18) 0.1676(9) 0.071(4) Uani 0.49(2) 1 d PDU B 2 N1 N 0.4897(7) 0.8772(8) 0.1950(4) 0.0601(19) Uani 1 1 d D . . C2 C 0.3997(9) 0.9541(9) 0.1584(5) 0.058(2) Uani 1 1 d D . . H2 H 0.3713 1.0333 0.1929 0.069 Uiso 1 1 calc R . . N3 N 0.3556(7) 0.9032(7) 0.0664(4) 0.0521(17) Uani 1 1 d D . . C4 C 0.4192(11) 0.7885(9) 0.0449(6) 0.072(3) Uani 1 1 d D . . H4 H 0.4069 0.7307 -0.0160 0.087 Uiso 1 1 calc R . . C5 C 0.5014(12) 0.7713(11) 0.1239(6) 0.078(3) Uani 1 1 d D . . H5 H 0.5574 0.6993 0.1297 0.093 Uiso 1 1 calc R . . C6 C 0.2534(11) 0.9621(12) 0.0023(7) 0.077(3) Uani 1 1 d D . . H6A H 0.2613 0.9292 -0.0636 0.115 Uiso 1 1 calc R . . H6B H 0.2795 1.0680 0.0170 0.115 Uiso 1 1 calc R . . H6C H 0.1519 0.9281 0.0114 0.115 Uiso 1 1 calc R . . C7 C 0.5643(12) 0.9009(15) 0.2947(6) 0.093(4) Uani 1 1 d D . . H7A H 0.5813 1.0049 0.3220 0.111 Uiso 1 1 calc R . . H7B H 0.6619 0.8756 0.2963 0.111 Uiso 1 1 calc R . . C8 C 0.4820(12) 0.8172(14) 0.3543(7) 0.091(3) Uani 1 1 d DU C . H8A H 0.4649 0.7129 0.3278 0.109 Uiso 1 1 calc R . . H8B H 0.3847 0.8428 0.3539 0.109 Uiso 1 1 calc R . . C9 C 0.5669(16) 0.8469(19) 0.4575(8) 0.129(5) Uani 1 1 d DU . . H9A H 0.5886 0.9517 0.4832 0.155 Uiso 0.68(4) 1 calc PR C 1 H9B H 0.5054 0.7960 0.4975 0.155 Uiso 0.68(4) 1 calc PR C 1 H9C H 0.6433 0.9373 0.4677 0.155 Uiso 0.32(4) 1 calc PR C 2 H9D H 0.4974 0.8615 0.5014 0.155 Uiso 0.32(4) 1 calc PR C 2 C10A C 0.709(2) 0.795(3) 0.4595(14) 0.103(8) Uiso 0.68(4) 1 d PDU C 1 H10A H 0.7619 0.8137 0.5250 0.155 Uiso 0.68(4) 1 calc PR C 1 H10B H 0.7697 0.8469 0.4206 0.155 Uiso 0.68(4) 1 calc PR C 1 H10C H 0.6865 0.6913 0.4343 0.155 Uiso 0.68(4) 1 calc PR C 1 C10B C 0.637(5) 0.730(3) 0.480(2) 0.082(14) Uiso 0.32(4) 1 d PDU C 2 H10D H 0.6913 0.7562 0.5456 0.123 Uiso 0.32(4) 1 calc PR C 2 H10E H 0.7061 0.7149 0.4369 0.123 Uiso 0.32(4) 1 calc PR C 2 H10F H 0.5619 0.6414 0.4734 0.123 Uiso 0.32(4) 1 calc PR C 2 N11 N 0.0890(7) 0.4943(7) 0.3103(4) 0.0507(16) Uani 1 1 d D . . C12 C 0.0478(9) 0.6092(8) 0.3556(6) 0.057(2) Uani 1 1 d D . . H12 H -0.0224 0.6581 0.3288 0.068 Uiso 1 1 calc R . . N13 N 0.1220(8) 0.6425(7) 0.4438(4) 0.0570(18) Uani 1 1 d D . . C14 C 0.2131(10) 0.5484(10) 0.4559(6) 0.065(2) Uani 1 1 d D . . H14 H 0.2777 0.5468 0.5124 0.078 Uiso 1 1 calc R . . C15 C 0.1938(10) 0.4593(10) 0.3729(5) 0.065(2) Uani 1 1 d D . . H15 H 0.2446 0.3841 0.3597 0.078 Uiso 1 1 calc R . . C16 C 0.1088(12) 0.7609(10) 0.5179(7) 0.076(3) Uani 1 1 d D . . H16A H 0.0827 0.8402 0.4881 0.114 Uiso 1 1 calc R . . H16B H 0.2031 0.7961 0.5617 0.114 Uiso 1 1 calc R . . H16C H 0.0317 0.7250 0.5528 0.114 Uiso 1 1 calc R . . C17 C 0.0332(9) 0.4227(9) 0.2109(5) 0.058(2) Uani 1 1 d D . . H17A H -0.0585 0.4527 0.1874 0.069 Uiso 1 1 calc R . . H17B H 0.0089 0.3167 0.2076 0.069 Uiso 1 1 calc R . . C18 C 0.1453(9) 0.4599(9) 0.1479(5) 0.055(2) Uani 1 1 d D . . H18A H 0.2433 0.4502 0.1787 0.066 Uiso 1 1 calc R . . H18B H 0.1530 0.5615 0.1394 0.066 Uiso 1 1 calc R . . C19 C 0.1009(11) 0.3611(10) 0.0517(5) 0.064(2) Uani 1 1 d D . . H19A H 0.0929 0.2596 0.0605 0.077 Uiso 1 1 calc R . . H19B H 0.0027 0.3707 0.0213 0.077 Uiso 1 1 calc R . . C20 C 0.2104(12) 0.3955(13) -0.0128(7) 0.079(3) Uani 1 1 d D . . H20A H 0.1773 0.3298 -0.0740 0.119 Uiso 1 1 calc R . . H20B H 0.3073 0.3835 0.0162 0.119 Uiso 1 1 calc R . . H20C H 0.2177 0.4955 -0.0224 0.119 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 P1 0.0655(15) 0.0551(14) 0.0430(11) 0.0095(10) 0.0133(10) 0.0208(10) F101 0.091(8) 0.098(9) 0.090(8) -0.020(7) 0.028(6) -0.013(6) F103 0.091(8) 0.098(9) 0.090(8) -0.020(7) 0.028(6) -0.013(6) F102 0.187(15) 0.186(13) 0.047(5) 0.044(7) 0.045(7) 0.044(11) F105 0.187(15) 0.186(13) 0.047(5) 0.044(7) 0.045(7) 0.044(11) F104 0.095(8) 0.098(10) 0.212(18) 0.081(10) 0.075(10) 0.063(7) F106 0.095(8) 0.098(10) 0.212(18) 0.081(10) 0.075(10) 0.063(7) F111 0.094(9) 0.076(9) 0.177(16) 0.068(10) 0.065(9) 0.035(7) F113 0.094(9) 0.076(9) 0.177(16) 0.068(10) 0.065(9) 0.035(7) F112 0.171(16) 0.126(10) 0.122(13) 0.012(10) -0.062(11) 0.070(11) F115 0.171(16) 0.126(10) 0.122(13) 0.012(10) -0.062(11) 0.070(11) F114 0.134(12) 0.087(8) 0.109(13) -0.028(9) 0.051(9) 0.045(7) F116 0.134(12) 0.087(8) 0.109(13) -0.028(9) 0.051(9) 0.045(7) P11 0.0553(13) 0.0659(15) 0.0445(11) 0.0037(10) 0.0133(10) 0.0174(10) F201 0.106(11) 0.097(7) 0.101(8) 0.053(6) 0.008(7) 0.026(7) F203 0.106(11) 0.097(7) 0.101(8) 0.053(6) 0.008(7) 0.026(7) F202 0.106(8) 0.115(10) 0.102(9) -0.009(7) 0.051(7) 0.036(7) F205 0.106(8) 0.115(10) 0.102(9) -0.009(7) 0.051(7) 0.036(7) F204 0.068(6) 0.073(6) 0.094(8) 0.023(6) 0.004(5) 0.006(5) F206 0.068(6) 0.073(6) 0.094(8) 0.023(6) 0.004(5) 0.006(5) F211 0.092(7) 0.084(7) 0.094(8) 0.003(6) 0.035(5) 0.051(6) F213 0.092(7) 0.084(7) 0.094(8) 0.003(6) 0.035(5) 0.051(6) F212 0.081(9) 0.138(10) 0.075(6) 0.054(6) 0.035(6) 0.019(6) F215 0.081(9) 0.138(10) 0.075(6) 0.054(6) 0.035(6) 0.019(6) F214 0.075(6) 0.092(8) 0.037(4) 0.009(5) -0.001(4) 0.007(5) F216 0.075(6) 0.092(8) 0.037(4) 0.009(5) -0.001(4) 0.007(5) N1 0.056(4) 0.071(5) 0.059(4) 0.010(4) 0.024(3) 0.019(4) C2 0.066(5) 0.053(5) 0.049(5) -0.007(4) 0.013(4) 0.010(4) N3 0.057(4) 0.055(4) 0.049(4) 0.018(3) 0.017(3) 0.012(3) C4 0.109(8) 0.063(6) 0.051(5) -0.002(4) 0.038(5) 0.026(5) C5 0.096(7) 0.091(7) 0.060(6) 0.020(6) 0.027(5) 0.040(6) C6 0.075(6) 0.088(7) 0.064(6) 0.019(5) 0.005(5) 0.012(5) C7 0.082(7) 0.131(10) 0.054(6) 0.017(6) -0.004(5) 0.009(7) C8 0.090(7) 0.109(9) 0.074(7) 0.034(7) 0.000(6) 0.020(6) C9 0.127(11) 0.173(14) 0.080(8) 0.033(9) -0.008(8) 0.028(10) N11 0.058(4) 0.058(4) 0.041(3) 0.016(3) 0.016(3) 0.013(3) C12 0.056(5) 0.052(5) 0.066(6) 0.018(4) 0.017(4) 0.010(4) N13 0.069(4) 0.057(4) 0.046(4) 0.014(3) 0.018(3) 0.009(3) C14 0.075(6) 0.081(6) 0.045(5) 0.018(5) 0.006(4) 0.032(5) C15 0.080(6) 0.078(6) 0.050(5) 0.023(5) 0.014(4) 0.039(5) C16 0.086(7) 0.069(6) 0.069(6) -0.006(5) 0.018(5) 0.016(5) C17 0.061(5) 0.066(5) 0.045(4) 0.017(4) 0.009(4) 0.006(4) C18 0.057(5) 0.060(5) 0.046(4) 0.001(4) 0.014(4) 0.015(4) C19 0.080(6) 0.064(5) 0.051(5) 0.007(4) 0.018(4) 0.018(5) C20 0.089(7) 0.100(8) 0.053(5) -0.002(5) 0.023(5) 0.036(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 F114 1.535(9) . ? P1 F105 1.540(8) . ? P1 F106 1.551(8) . ? P1 F115 1.553(9) . ? P1 F103 1.554(9) . ? P1 F112 1.565(9) . ? P1 F104 1.570(8) . ? P1 F102 1.571(8) . ? P1 F111 1.574(9) . ? P1 F113 1.585(9) . ? P1 F116 1.587(8) . ? P1 F101 1.598(9) . ? P11 F203 1.529(9) . ? P11 F212 1.548(9) . ? P11 F206 1.572(9) . ? P11 F214 1.573(8) . ? P11 F205 1.574(9) . ? P11 F202 1.580(9) . ? P11 F204 1.580(9) . ? P11 F213 1.585(8) . ? P11 F216 1.588(8) . ? P11 F211 1.593(9) . ? P11 F215 1.602(8) . ? P11 F201 1.634(8) . ? N1 C2 1.327(9) . ? N1 C5 1.368(10) . ? N1 C7 1.477(10) . ? C2 N3 1.327(9) . ? C2 H2 0.9500 . ? N3 C4 1.366(10) . ? N3 C6 1.485(10) . ? C4 C5 1.335(11) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.465(11) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.547(12) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10B 1.458(17) . ? C9 C10A 1.504(16) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 H9C 0.9900 . ? C9 H9D 0.9900 . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C10B H10D 0.9800 . ? C10B H10E 0.9800 . ? C10B H10F 0.9800 . ? N11 C12 1.349(9) . ? N11 C15 1.364(9) . ? N11 C17 1.473(9) . ? C12 N13 1.326(9) . ? C12 H12 0.9500 . ? N13 C14 1.370(9) . ? N13 C16 1.480(10) . ? C14 C15 1.336(10) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.517(9) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.519(9) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.509(11) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 F114 P1 F105 119.8(10) . . ? F114 P1 F106 147.0(10) . . ? F105 P1 F106 90.5(8) . . ? F114 P1 F115 92.4(9) . . ? F105 P1 F115 34.2(9) . . ? F106 P1 F115 120.5(10) . . ? F114 P1 F103 78.9(11) . . ? F105 P1 F103 90.1(7) . . ? F106 P1 F103 89.3(8) . . ? F115 P1 F103 105.3(11) . . ? F114 P1 F112 91.7(8) . . ? F105 P1 F112 142.8(10) . . ? F106 P1 F112 55.4(9) . . ? F115 P1 F112 175.8(9) . . ? F103 P1 F112 76.3(11) . . ? F114 P1 F104 33.0(8) . . ? F105 P1 F104 90.8(8) . . ? F106 P1 F104 176.8(6) . . ? F115 P1 F104 59.9(9) . . ? F103 P1 F104 93.6(8) . . ? F112 P1 F104 124.0(10) . . ? F114 P1 F102 59.4(10) . . ? F105 P1 F102 177.4(8) . . ? F106 P1 F102 90.8(8) . . ? F115 P1 F102 143.6(10) . . ? F103 P1 F102 92.1(7) . . ? F112 P1 F102 39.3(9) . . ? F104 P1 F102 87.8(8) . . ? F114 P1 F111 92.5(8) . . ? F105 P1 F111 107.5(12) . . ? F106 P1 F111 89.8(10) . . ? F115 P1 F111 90.2(9) . . ? F103 P1 F111 162.4(11) . . ? F112 P1 F111 88.8(9) . . ? F104 P1 F111 86.9(10) . . ? F102 P1 F111 70.3(11) . . ? F114 P1 F113 89.5(8) . . ? F105 P1 F113 70.6(11) . . ? F106 P1 F113 89.0(9) . . ? F115 P1 F113 88.7(9) . . ? F103 P1 F113 19.5(10) . . ? F112 P1 F113 92.2(9) . . ? F104 P1 F113 94.2(9) . . ? F102 P1 F113 111.6(11) . . ? F111 P1 F113 177.8(8) . . ? F114 P1 F116 178.6(8) . . ? F105 P1 F116 60.5(9) . . ? F106 P1 F116 32.1(8) . . ? F115 P1 F116 88.4(8) . . ? F103 P1 F116 99.8(11) . . ? F112 P1 F116 87.5(8) . . ? F104 P1 F116 148.0(9) . . ? F102 P1 F116 120.3(10) . . ? F111 P1 F116 88.7(8) . . ? F113 P1 F116 89.4(8) . . ? F114 P1 F101 101.4(11) . . ? F105 P1 F101 93.1(7) . . ? F106 P1 F101 88.4(8) . . ? F115 P1 F101 78.6(12) . . ? F103 P1 F101 176.1(8) . . ? F112 P1 F101 99.8(12) . . ? F104 P1 F101 88.6(8) . . ? F102 P1 F101 84.7(7) . . ? F111 P1 F101 14.5(12) . . ? F113 P1 F101 163.5(11) . . ? F116 P1 F101 79.9(11) . . ? F203 P11 F212 156.0(8) . . ? F203 P11 F206 91.3(7) . . ? F212 P11 F206 75.8(9) . . ? F203 P11 F214 104.1(10) . . ? F212 P11 F214 89.5(7) . . ? F206 P11 F214 164.6(9) . . ? F203 P11 F205 91.3(8) . . ? F212 P11 F205 109.2(9) . . ? F206 P11 F205 92.5(9) . . ? F214 P11 F205 88.0(11) . . ? F203 P11 F202 96.6(8) . . ? F212 P11 F202 63.7(8) . . ? F206 P11 F202 89.6(8) . . ? F214 P11 F202 87.8(10) . . ? F205 P11 F202 171.7(9) . . ? F203 P11 F204 90.4(7) . . ? F212 P11 F204 100.5(10) . . ? F206 P11 F204 173.8(9) . . ? F214 P11 F204 14.6(9) . . ? F205 P11 F204 93.4(9) . . ? F202 P11 F204 84.3(8) . . ? F203 P11 F213 65.4(7) . . ? F212 P11 F213 93.5(7) . . ? F206 P11 F213 87.7(9) . . ? F214 P11 F213 97.9(8) . . ? F205 P11 F213 156.7(8) . . ? F202 P11 F213 31.4(6) . . ? F204 P11 F213 87.6(9) . . ? F203 P11 F216 76.4(10) . . ? F212 P11 F216 93.1(7) . . ? F206 P11 F216 17.6(7) . . ? F214 P11 F216 171.6(8) . . ? F205 P11 F216 83.5(11) . . ? F202 P11 F216 100.6(9) . . ? F204 P11 F216 166.3(10) . . ? F213 P11 F216 90.0(7) . . ? F203 P11 F211 108.8(9) . . ? F212 P11 F211 91.1(8) . . ? F206 P11 F211 88.0(11) . . ? F214 P11 F211 87.8(8) . . ? F205 P11 F211 18.0(10) . . ? F202 P11 F211 154.5(9) . . ? F204 P11 F211 97.1(10) . . ? F213 P11 F211 172.7(8) . . ? F216 P11 F211 84.1(8) . . ? F203 P11 F215 24.6(7) . . ? F212 P11 F215 179.5(7) . . ? F206 P11 F215 104.5(8) . . ? F214 P11 F215 90.2(7) . . ? F205 P11 F215 70.4(9) . . ? F202 P11 F215 116.7(9) . . ? F204 P11 F215 79.2(10) . . ? F213 P11 F215 86.9(7) . . ? F216 P11 F215 87.2(6) . . ? F211 P11 F215 88.4(7) . . ? F203 P11 F201 177.4(8) . . ? F212 P11 F201 25.6(6) . . ? F206 P11 F201 87.8(7) . . ? F214 P11 F201 76.8(9) . . ? F205 P11 F201 86.3(8) . . ? F202 P11 F201 85.8(8) . . ? F204 P11 F201 90.8(7) . . ? F213 P11 F201 117.0(7) . . ? F216 P11 F201 102.3(10) . . ? F211 P11 F201 68.7(9) . . ? F215 P11 F201 153.8(8) . . ? C2 N1 C5 108.0(7) . . ? C2 N1 C7 126.3(8) . . ? C5 N1 C7 125.6(9) . . ? N3 C2 N1 109.5(7) . . ? N3 C2 H2 125.2 . . ? N1 C2 H2 125.2 . . ? C2 N3 C4 107.0(7) . . ? C2 N3 C6 124.5(8) . . ? C4 N3 C6 128.4(8) . . ? C5 C4 N3 108.6(7) . . ? C5 C4 H4 125.7 . . ? N3 C4 H4 125.7 . . ? C4 C5 N1 106.8(8) . . ? C4 C5 H5 126.6 . . ? N1 C5 H5 126.6 . . ? N3 C6 H6A 109.5 . . ? H6C C6 H6A 109.5 . . ? N3 C6 H6C 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? H6C C6 H6B 109.5 . . ? C8 C7 N1 114.1(8) . . ? C8 C7 H7A 108.7 . . ? N1 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? N1 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 C9 111.3(9) . . ? C7 C8 H8A 109.4 . . ? C9 C8 H8A 109.4 . . ? C7 C8 H8B 109.4 . . ? C9 C8 H8B 109.4 . . ? H8A C8 H8B 108.0 . . ? C10B C9 C10A 36.8(15) . . ? C10B C9 C8 113.2(17) . . ? C10A C9 C8 109.6(13) . . ? C10B C9 H9A 132.9 . . ? C10A C9 H9A 109.7 . . ? C8 C9 H9A 109.7 . . ? C10B C9 H9B 74.5 . . ? C10A C9 H9B 109.7 . . ? C8 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C10B C9 H9C 108.9 . . ? C10A C9 H9C 76.4 . . ? C8 C9 H9C 108.9 . . ? H9A C9 H9C 36.5 . . ? H9B C9 H9C 135.5 . . ? C10B C9 H9D 108.9 . . ? C10A C9 H9D 137.1 . . ? C8 C9 H9D 108.9 . . ? H9A C9 H9D 73.4 . . ? H9B C9 H9D 37.9 . . ? H9C C9 H9D 107.8 . . ? C9 C10A H10A 109.5 . . ? C9 C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9 C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C9 C10B H10D 109.5 . . ? C9 C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C9 C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C12 N11 C15 107.2(6) . . ? C12 N11 C17 126.1(7) . . ? C15 N11 C17 126.7(7) . . ? N13 C12 N11 108.4(7) . . ? N13 C12 H12 125.8 . . ? N11 C12 H12 125.8 . . ? C12 N13 C14 108.8(7) . . ? C12 N13 C16 126.0(8) . . ? C14 N13 C16 125.2(7) . . ? C15 C14 N13 106.8(7) . . ? C15 C14 H14 126.6 . . ? N13 C14 H14 126.6 . . ? C14 C15 N11 108.7(7) . . ? C14 C15 H15 125.7 . . ? N11 C15 H15 125.7 . . ? N13 C16 H16A 109.5 . . ? N13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N11 C17 C18 111.8(6) . . ? N11 C17 H17A 109.3 . . ? C18 C17 H17A 109.3 . . ? N11 C17 H17B 109.3 . . ? C18 C17 H17B 109.3 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C19 110.9(6) . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 108.0 . . ? C20 C19 C18 112.2(7) . . ? C20 C19 H19A 109.2 . . ? C18 C19 H19A 109.2 . . ? C20 C19 H19B 109.2 . . ? C18 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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 C5 N1 C2 N3 -1.1(10) . . . . ? C7 N1 C2 N3 178.9(7) . . . . ? N1 C2 N3 C4 0.8(9) . . . . ? N1 C2 N3 C6 179.7(7) . . . . ? C2 N3 C4 C5 -0.2(10) . . . . ? C6 N3 C4 C5 -179.0(9) . . . . ? N3 C4 C5 N1 -0.5(11) . . . . ? C2 N1 C5 C4 1.0(11) . . . . ? C7 N1 C5 C4 -179.1(8) . . . . ? C2 N1 C7 C8 92.3(13) . . . . ? C5 N1 C7 C8 -87.6(13) . . . . ? N1 C7 C8 C9 179.8(12) . . . . ? C7 C8 C9 C10B -104(2) . . . . ? C7 C8 C9 C10A -64.4(19) . . . . ? C15 N11 C12 N13 -1.3(8) . . . . ? C17 N11 C12 N13 -180.0(6) . . . . ? N11 C12 N13 C14 0.3(9) . . . . ? N11 C12 N13 C16 -179.3(7) . . . . ? C12 N13 C14 C15 0.9(10) . . . . ? C16 N13 C14 C15 -179.5(8) . . . . ? N13 C14 C15 N11 -1.7(11) . . . . ? C12 N11 C15 C14 1.8(10) . . . . ? C17 N11 C15 C14 -179.5(7) . . . . ? C12 N11 C17 C18 105.1(9) . . . . ? C15 N11 C17 C18 -73.3(10) . . . . ? N11 C17 C18 C19 167.5(8) . . . . ? C17 C18 C19 C20 180.0(8) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 23.34 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.516 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.081 data_beta_bmim_PF6_0.07GPa _database_code_depnum_ccdc_archive 'CCDC 909174' _refine_special_details ; The Following ALERTS were generated by PLATON checkcif4 REFLT03_ALERT_3_A Reflection count < 85% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 14.91 From the CIF: _diffrn_reflns_theta_full 14.91 From the CIF: _reflns_number_total 1063 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2069 Completeness (_total/calc) 51.38% REFNR01_ALERT_3_A Ratio of reflections to parameters is < 6 for a centrosymmetric structure sine(theta)/lambda 0.4588 Proportion of unique data used 1.0000 Ratio reflections to parameters 2.9044 THETM01_ALERT_3_A The value of sine(theta_max)/wavelength is less than 0.550 Calculated sin(theta_max)/wavelength = 0.4588 PLAT022_ALERT_3_A Ratio Unique / Expected Reflections (too) Low .. 0.514 PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.514 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.3 PLAT088_ALERT_3_A Poor Data / Parameter Ratio .................... 3.12 The crystal was grown and measured in situ in a DAC. These alerts are not uncommon for high-pressure data. The geometry of the diamond-anvil cell severely restricts the amount of recirpocal space that can be accessed, resulting in a poor completeness. This is more evident for lower-symmetry crystal systems (triclinic in this case). Two data sets were collected with the DAC in two different orientations on the goniometer head to similate two values of chi and improve data completeness. To imptove data completeness, silver radiation was used. The heavy use of restraints (809) increases the data to parameter ratio to 5.5 and the data quality is very good so that refinement of an anisotropic model is unproblematic. Diffraction data were collected with the crystal at phase boundary conditions, i.e. coexisting with the liquid phase. An isotropic description of the displacement parameters is for this data set insufficient, in particular given the presence of rotationally disordered PF6 groups. This is also exemplified by comparing the reported refinement with an isotropic model, for which a significant increase in the R-factor is obtained (final R1 ca. 14%). PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for P1 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for P11 PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds ............... 0.0280 Ang PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C5 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C17 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N11 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 Noted, no action taken. The structure is twinned and disordered and this is high- pressure data. It is possible that the degree of disorder is higher than the one modelled. PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 3 Disordered carbon atoms were refined isotropically. PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? The one given is more meaningful. ; _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C8 H15 N2, P F6' _chemical_formula_sum 'C8 H15 F6 N2 P' _chemical_formula_weight 284.19 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 triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5818(13) _cell_length_b 9.5826(9) _cell_length_c 14.5801(10) _cell_angle_alpha 99.219(10) _cell_angle_beta 99.252(6) _cell_angle_gamma 99.667(10) _cell_volume 1278.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1186 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 4.71 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_rad 0.25 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.145 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SHADE (Parsons, 2004) # SADABS V.2008/1 # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_T_max 0.86 _exptl_special_details ; crystal grown and measured in a diamond-anvil cell ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.56085 _diffrn_radiation_type AgK\a _diffrn_radiation_source 'Ag microsource' _diffrn_radiation_monochromator 'INCOATEC multilayer optics' _diffrn_measurement_device 'Bruker AXS APEX II' _diffrn_measurement_device_type Area _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #_diffrn_reflns_limit_h_max 8 #_diffrn_reflns_limit_h_min -8 #_diffrn_reflns_limit_k_max 5 #_diffrn_reflns_limit_k_min -5 #_diffrn_reflns_limit_l_max 13 #_diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 10400 _diffrn_reflns_av_R_equivalents 0.04 _diffrn_reflns_av_sigmaI/netI 0.0228 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.14 _diffrn_reflns_theta_max 14.91 _reflns_number_total 1063 _reflns_number_gt 815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_publication_material 'PLATON, XCIF, ENCIFER, SHELXLE' _computing_molecular_graphics MERCURY _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^)+(0.1363P)^2^+2.0849P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1064 _refine_ls_number_parameters 341 _refine_ls_number_restraints 809 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0740 _refine_ls_wR_factor_ref 0.2319 _refine_ls_wR_factor_gt 0.2113 _refine_ls_goodness_of_fit_ref 1.125 _refine_ls_restrained_S_all 1.162 _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 0.0314(5) -0.0340(7) 0.2494(4) 0.102(2) Uani 1 1 d DU . . F101 F -0.080(3) -0.178(2) 0.223(2) 0.201(11) Uani 0.50 1 d PDU A 1 F103 F 0.145(3) 0.109(3) 0.272(2) 0.201(11) Uani 0.50 1 d PDU A 1 F102 F 0.012(3) -0.017(4) 0.3541(11) 0.177(10) Uani 0.50 1 d PDU A 1 F105 F 0.049(4) -0.047(3) 0.1454(11) 0.177(10) Uani 0.50 1 d PDU A 1 F104 F -0.090(2) 0.053(3) 0.2290(17) 0.143(7) Uani 0.50 1 d PDU A 1 F106 F 0.155(2) -0.114(3) 0.2731(17) 0.143(7) Uani 0.50 1 d PDU A 1 F111 F -0.089(3) -0.152(2) 0.263(2) 0.153(8) Uani 0.50 1 d PDU A 2 F113 F 0.158(3) 0.079(3) 0.232(2) 0.153(8) Uani 0.50 1 d PDU A 2 F112 F 0.133(3) -0.054(4) 0.3394(15) 0.195(10) Uani 0.50 1 d PDU A 2 F115 F -0.064(3) -0.016(4) 0.1586(15) 0.195(10) Uani 0.50 1 d PDU A 2 F114 F -0.019(3) 0.091(2) 0.3074(18) 0.139(7) Uani 0.50 1 d PDU A 2 F116 F 0.093(3) -0.151(2) 0.1905(18) 0.139(7) Uani 0.50 1 d PDU A 2 P11 P 0.6113(6) 0.3823(7) 0.2506(4) 0.106(2) Uani 1 1 d DU . . F201 F 0.617(4) 0.277(3) 0.3229(16) 0.191(9) Uani 0.50 1 d PDU B 1 F203 F 0.591(4) 0.473(3) 0.1748(17) 0.191(9) Uani 0.50 1 d PDU B 1 F202 F 0.525(3) 0.468(3) 0.3137(15) 0.162(8) Uani 0.50 1 d PDU B 1 F205 F 0.671(3) 0.271(3) 0.1874(16) 0.162(8) Uani 0.50 1 d PDU B 1 F204 F 0.752(2) 0.476(3) 0.301(2) 0.192(10) Uani 0.50 1 d PDU B 1 F206 F 0.457(2) 0.286(3) 0.2024(19) 0.192(10) Uani 0.50 1 d PDU B 1 F211 F 0.733(3) 0.302(3) 0.284(2) 0.193(9) Uani 0.50 1 d PDU B 2 F213 F 0.507(3) 0.485(3) 0.229(2) 0.193(9) Uani 0.50 1 d PDU B 2 F212 F 0.520(3) 0.318(3) 0.3150(16) 0.173(8) Uani 0.50 1 d PDU B 2 F215 F 0.710(3) 0.441(3) 0.1837(15) 0.173(8) Uani 0.50 1 d PDU B 2 F214 F 0.700(3) 0.509(3) 0.3327(13) 0.166(9) Uani 0.50 1 d PDU B 2 F216 F 0.535(3) 0.260(3) 0.1700(13) 0.166(9) Uani 0.50 1 d PDU B 2 N1 N 0.5042(18) 0.890(2) 0.1910(8) 0.115(5) Uani 1 1 d DU . . C2 C 0.396(2) 0.946(2) 0.1540(11) 0.113(6) Uani 1 1 d DU . . H2 H 0.3545 1.0141 0.1875 0.136 Uiso 1 1 calc R . . N3 N 0.3560(17) 0.893(2) 0.0636(10) 0.109(6) Uani 1 1 d DU . . C4 C 0.438(3) 0.794(2) 0.0453(12) 0.134(7) Uani 1 1 d DU . . H4 H 0.4345 0.7398 -0.0141 0.161 Uiso 1 1 calc R . . C5 C 0.526(3) 0.786(3) 0.1257(13) 0.146(7) Uani 1 1 d DU . . H5 H 0.5880 0.7221 0.1336 0.175 Uiso 1 1 calc R . . C6 C 0.250(2) 0.938(3) -0.0035(14) 0.156(8) Uani 1 1 d DU . . H6A H 0.2530 0.8940 -0.0669 0.234 Uiso 1 1 calc R . . H6B H 0.2729 1.0414 0.0031 0.234 Uiso 1 1 calc R . . H6C H 0.1555 0.9096 0.0093 0.234 Uiso 1 1 calc R . . C7 C 0.583(3) 0.933(2) 0.2896(10) 0.142(7) Uani 1 1 d DU D . H7A H 0.5664 1.0264 0.3171 0.170 Uiso 1 1 calc R . . H7B H 0.6857 0.9413 0.2911 0.170 Uiso 1 1 calc R . . C8 C 0.533(3) 0.822(2) 0.3466(11) 0.139(8) Uani 1 1 d DU . . H8A H 0.5308 0.7257 0.3132 0.167 Uiso 0.70 1 calc PR C 1 H8B H 0.4371 0.8286 0.3581 0.167 Uiso 0.70 1 calc PR C 1 H8C H 0.5739 0.7374 0.3320 0.167 Uiso 0.30 1 calc PR C 2 H8D H 0.4287 0.7936 0.3316 0.167 Uiso 0.30 1 calc PR C 2 C9A C 0.644(3) 0.858(4) 0.4412(14) 0.136(10) Uiso 0.70 1 d PDU D 1 H9A H 0.7333 0.8298 0.4313 0.164 Uiso 0.70 1 calc PR D 1 H9B H 0.6635 0.9611 0.4664 0.164 Uiso 0.70 1 calc PR D 1 C10A C 0.579(5) 0.776(5) 0.5092(19) 0.18(2) Uiso 0.70 1 d PDU D 1 H10A H 0.4755 0.7644 0.4947 0.276 Uiso 0.70 1 calc PR D 1 H10B H 0.6143 0.8292 0.5727 0.276 Uiso 0.70 1 calc PR D 1 H10C H 0.6048 0.6834 0.5033 0.276 Uiso 0.70 1 calc PR D 1 C9B C 0.583(7) 0.892(4) 0.4518(13) 0.132(16) Uiso 0.30 1 d PDU D 2 H9C H 0.6562 0.9784 0.4592 0.158 Uiso 0.30 1 calc PR D 2 H9D H 0.5027 0.9176 0.4785 0.158 Uiso 0.30 1 calc PR D 2 C10B C 0.645(6) 0.783(6) 0.501(2) 0.082(16) Uiso 0.30 1 d PDU D 2 H10D H 0.7183 0.7503 0.4702 0.122 Uiso 0.30 1 calc PR D 2 H10E H 0.5700 0.7018 0.4997 0.122 Uiso 0.30 1 calc PR D 2 H10F H 0.6873 0.8265 0.5662 0.122 Uiso 0.30 1 calc PR D 2 N11 N 0.1009(17) 0.5019(17) 0.3073(8) 0.095(5) Uani 1 1 d DU . . C12 C 0.0396(19) 0.598(2) 0.3472(10) 0.089(5) Uani 1 1 d DU . . H12 H -0.0381 0.6307 0.3173 0.107 Uiso 1 1 calc R . . N13 N 0.1030(16) 0.6422(19) 0.4371(9) 0.090(5) Uani 1 1 d DU . . C14 C 0.207(2) 0.566(2) 0.4505(11) 0.115(6) Uani 1 1 d DU . . H14 H 0.2685 0.5722 0.5077 0.138 Uiso 1 1 calc R . . C15 C 0.208(2) 0.481(2) 0.3705(11) 0.116(6) Uani 1 1 d DU . . H15 H 0.2706 0.4180 0.3603 0.140 Uiso 1 1 calc R . . C16 C 0.070(3) 0.753(2) 0.5062(12) 0.141(8) Uani 1 1 d DU . . H16A H 0.0031 0.8026 0.4748 0.211 Uiso 1 1 calc R . . H16B H 0.1570 0.8207 0.5368 0.211 Uiso 1 1 calc R . . H16C H 0.0277 0.7091 0.5526 0.211 Uiso 1 1 calc R . . C17 C 0.053(3) 0.422(3) 0.2073(10) 0.135(7) Uani 1 1 d DU . . H17A H -0.0433 0.4353 0.1826 0.162 Uiso 1 1 calc R . . H17B H 0.0490 0.3197 0.2052 0.162 Uiso 1 1 calc R . . C18 C 0.153(2) 0.475(3) 0.1492(9) 0.126(7) Uani 1 1 d DU F . H18A H 0.2518 0.4807 0.1803 0.151 Uiso 1 1 calc R . . H18B H 0.1421 0.5712 0.1397 0.151 Uiso 1 1 calc R . . C19 C 0.118(3) 0.369(3) 0.0523(12) 0.162(10) Uani 1 1 d DU . . H19A H 0.1273 0.2726 0.0614 0.194 Uiso 0.70 1 calc PR E 1 H19B H 0.0208 0.3657 0.0199 0.194 Uiso 0.70 1 calc PR E 1 H19C H 0.0393 0.2912 0.0525 0.194 Uiso 0.30 1 calc PR E 2 H19D H 0.0877 0.4192 0.0022 0.194 Uiso 0.30 1 calc PR E 2 C20A C 0.226(4) 0.425(4) -0.0044(19) 0.152(13) Uiso 0.70 1 d PDU F 1 H20A H 0.2097 0.3624 -0.0650 0.228 Uiso 0.70 1 calc PR F 1 H20B H 0.3222 0.4290 0.0289 0.228 Uiso 0.70 1 calc PR F 1 H20C H 0.2156 0.5204 -0.0132 0.228 Uiso 0.70 1 calc PR F 1 C20B C 0.247(6) 0.307(8) 0.033(4) 0.17(3) Uiso 0.30 1 d PDU F 2 H20D H 0.2222 0.2430 -0.0279 0.257 Uiso 0.30 1 calc PR F 2 H20E H 0.2757 0.2550 0.0811 0.257 Uiso 0.30 1 calc PR F 2 H20F H 0.3251 0.3839 0.0320 0.257 Uiso 0.30 1 calc PR F 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 0.075(5) 0.137(9) 0.095(3) 0.015(5) 0.020(4) 0.027(4) F101 0.140(16) 0.176(17) 0.26(2) 0.017(18) 0.013(18) -0.012(15) F103 0.140(16) 0.176(17) 0.26(2) 0.017(18) 0.013(18) -0.012(15) F102 0.23(2) 0.27(3) 0.088(9) 0.082(12) 0.051(12) 0.16(2) F105 0.23(2) 0.27(3) 0.088(9) 0.082(12) 0.051(12) 0.16(2) F104 0.117(12) 0.24(2) 0.109(15) 0.072(15) 0.030(11) 0.094(12) F106 0.117(12) 0.24(2) 0.109(15) 0.072(15) 0.030(11) 0.094(12) F111 0.124(13) 0.129(16) 0.24(2) 0.036(14) 0.110(14) 0.050(12) F113 0.124(13) 0.129(16) 0.24(2) 0.036(14) 0.110(14) 0.050(12) F112 0.20(2) 0.27(3) 0.104(13) 0.031(15) -0.033(15) 0.103(19) F115 0.20(2) 0.27(3) 0.104(13) 0.031(15) -0.033(15) 0.103(19) F114 0.174(18) 0.131(15) 0.123(14) 0.004(12) 0.063(15) 0.048(13) F116 0.174(18) 0.131(15) 0.123(14) 0.004(12) 0.063(15) 0.048(13) P11 0.095(5) 0.146(8) 0.076(3) 0.016(4) 0.009(3) 0.035(4) F201 0.23(2) 0.25(2) 0.147(14) 0.104(15) 0.083(15) 0.103(19) F203 0.23(2) 0.25(2) 0.147(14) 0.104(15) 0.083(15) 0.103(19) F202 0.160(17) 0.21(2) 0.129(15) 0.008(13) 0.064(13) 0.076(16) F205 0.160(17) 0.21(2) 0.129(15) 0.008(13) 0.064(13) 0.076(16) F204 0.075(10) 0.23(2) 0.23(2) -0.015(15) -0.006(12) 0.015(13) F206 0.075(10) 0.23(2) 0.23(2) -0.015(15) -0.006(12) 0.015(13) F211 0.148(17) 0.29(3) 0.17(2) 0.059(18) 0.010(15) 0.12(2) F213 0.148(17) 0.29(3) 0.17(2) 0.059(18) 0.010(15) 0.12(2) F212 0.163(19) 0.22(2) 0.161(14) 0.026(13) 0.113(16) 0.030(15) F215 0.163(19) 0.22(2) 0.161(14) 0.026(13) 0.113(16) 0.030(15) F214 0.136(16) 0.228(19) 0.091(8) -0.039(11) 0.016(11) -0.012(14) F216 0.136(16) 0.228(19) 0.091(8) -0.039(11) 0.016(11) -0.012(14) N1 0.107(10) 0.133(14) 0.093(7) -0.006(8) 0.026(7) 0.013(10) C2 0.104(12) 0.120(15) 0.106(8) -0.002(10) 0.029(9) 0.008(10) N3 0.085(10) 0.140(15) 0.097(8) 0.023(9) 0.033(7) -0.008(9) C4 0.167(16) 0.142(17) 0.088(8) 0.000(9) 0.038(10) 0.026(11) C5 0.168(15) 0.156(17) 0.115(10) -0.002(10) 0.030(11) 0.060(11) C6 0.097(15) 0.20(2) 0.154(14) 0.047(15) -0.003(11) -0.011(13) C7 0.127(13) 0.164(16) 0.110(9) 0.003(9) 0.009(8) -0.002(13) C8 0.159(15) 0.129(16) 0.116(10) 0.012(9) -0.005(11) 0.031(14) N11 0.099(10) 0.116(12) 0.085(6) 0.028(7) 0.017(6) 0.057(9) C12 0.084(11) 0.098(13) 0.100(8) 0.032(8) 0.012(8) 0.050(9) N13 0.089(9) 0.107(12) 0.094(7) 0.026(8) 0.024(7) 0.059(9) C14 0.129(12) 0.148(16) 0.089(7) 0.030(9) 0.005(8) 0.093(10) C15 0.128(13) 0.158(15) 0.096(9) 0.034(10) 0.025(8) 0.107(10) C16 0.172(19) 0.137(18) 0.135(12) 0.007(11) 0.065(14) 0.074(14) C17 0.155(15) 0.155(17) 0.094(8) 0.009(9) 0.018(7) 0.049(14) C18 0.107(12) 0.20(2) 0.081(8) 0.007(10) 0.013(8) 0.094(15) C19 0.163(17) 0.22(2) 0.101(10) -0.013(12) 0.023(11) 0.08(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 P1 F111 1.536(13) . ? P1 F115 1.538(13) . ? P1 F105 1.540(12) . ? P1 F106 1.540(12) . ? P1 F114 1.543(13) . ? P1 F101 1.549(14) . ? P1 F103 1.551(13) . ? P1 F102 1.554(12) . ? P1 F104 1.558(13) . ? P1 F112 1.560(13) . ? P1 F116 1.560(12) . ? P1 F113 1.566(13) . ? P11 F204 1.490(13) . ? P11 F216 1.508(12) . ? P11 F212 1.518(13) . ? P11 F203 1.523(13) . ? P11 F205 1.541(13) . ? P11 F213 1.548(13) . ? P11 F202 1.557(13) . ? P11 F211 1.562(14) . ? P11 F215 1.569(12) . ? P11 F201 1.572(13) . ? P11 F214 1.577(13) . ? P11 F206 1.594(13) . ? N1 C2 1.329(18) . ? N1 C5 1.329(17) . ? N1 C7 1.471(16) . ? C2 N3 1.305(15) . ? C2 H2 0.9300 . ? N3 C4 1.345(18) . ? N3 C6 1.465(17) . ? C4 C5 1.351(18) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8 1.511(6) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9B 1.534(17) . ? C8 C9A 1.549(16) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C8 H8D 0.9700 . ? C9A C10A 1.505(14) . ? C9A H9A 0.9700 . ? C9A H9B 0.9700 . ? C10A H10A 0.9600 . ? C10A H10B 0.9600 . ? C10A H10C 0.9600 . ? C9B C10B 1.511(17) . ? C9B H9C 0.9700 . ? C9B H9D 0.9700 . ? C10B H10D 0.9600 . ? C10B H10E 0.9600 . ? C10B H10F 0.9600 . ? N11 C12 1.282(16) . ? N11 C15 1.329(16) . ? N11 C17 1.494(16) . ? C12 N13 1.321(14) . ? C12 H12 0.9300 . ? N13 C14 1.337(17) . ? N13 C16 1.455(16) . ? C14 C15 1.315(17) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.464(16) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.555(17) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20B 1.50(2) . ? C19 C20A 1.51(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C19 H19C 0.9700 . ? C19 H19D 0.9700 . ? C20A H20A 0.9600 . ? C20A H20B 0.9600 . ? C20A H20C 0.9600 . ? C20B H20D 0.9600 . ? C20B H20E 0.9600 . ? C20B H20F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F111 P1 F115 90.2(12) . . ? F105 P1 F106 92.0(11) . . ? F111 P1 F114 95.1(11) . . ? F115 P1 F114 90.4(13) . . ? F105 P1 F101 89.6(13) . . ? F106 P1 F101 90.8(13) . . ? F114 P1 F101 114.6(17) . . ? F105 P1 F103 88.2(13) . . ? F106 P1 F103 88.5(13) . . ? F101 P1 F103 177.7(14) . . ? F105 P1 F102 178.4(13) . . ? F106 P1 F102 89.5(11) . . ? F101 P1 F102 90.9(13) . . ? F103 P1 F102 91.3(13) . . ? F111 P1 F104 86.0(17) . . ? F105 P1 F104 89.4(11) . . ? F106 P1 F104 177.4(12) . . ? F101 P1 F104 91.5(13) . . ? F103 P1 F104 89.3(13) . . ? F102 P1 F104 89.1(11) . . ? F111 P1 F112 90.8(12) . . ? F115 P1 F112 177.9(14) . . ? F114 P1 F112 91.3(12) . . ? F111 P1 F116 89.5(11) . . ? F115 P1 F116 90.3(12) . . ? F114 P1 F116 175.3(11) . . ? F112 P1 F116 88.0(12) . . ? F111 P1 F113 176.2(10) . . ? F115 P1 F113 90.0(12) . . ? F114 P1 F113 88.6(11) . . ? F112 P1 F113 88.8(12) . . ? F116 P1 F113 86.8(10) . . ? F216 P11 F212 89.6(11) . . ? F204 P11 F203 93.6(13) . . ? F204 P11 F205 97.9(13) . . ? F203 P11 F205 93.2(11) . . ? F216 P11 F213 95.6(13) . . ? F212 P11 F213 91.8(13) . . ? F204 P11 F202 92.0(12) . . ? F203 P11 F202 92.3(13) . . ? F205 P11 F202 168.3(13) . . ? F216 P11 F211 93.8(13) . . ? F212 P11 F211 90.7(12) . . ? F213 P11 F211 170.3(14) . . ? F216 P11 F215 89.0(11) . . ? F212 P11 F215 176.6(14) . . ? F213 P11 F215 91.4(12) . . ? F211 P11 F215 86.3(13) . . ? F204 P11 F201 92.3(13) . . ? F216 P11 F201 91.8(17) . . ? F203 P11 F201 174.0(14) . . ? F205 P11 F201 85.6(12) . . ? F202 P11 F201 87.9(11) . . ? F216 P11 F214 176.5(12) . . ? F212 P11 F214 93.1(11) . . ? F203 P11 F214 96.6(18) . . ? F213 P11 F214 86.6(12) . . ? F211 P11 F214 83.9(12) . . ? F215 P11 F214 88.2(11) . . ? F201 P11 F214 88.8(18) . . ? F204 P11 F206 176.2(13) . . ? F203 P11 F206 87.8(12) . . ? F205 P11 F206 85.5(11) . . ? F202 P11 F206 84.4(12) . . ? F201 P11 F206 86.2(12) . . ? C2 N1 C5 109.1(14) . . ? C2 N1 C7 124.8(19) . . ? C5 N1 C7 126.1(19) . . ? N3 C2 N1 109.9(16) . . ? N3 C2 H2 125.1 . . ? N1 C2 H2 125.1 . . ? C2 N3 C4 105.6(15) . . ? C2 N3 C6 126.2(19) . . ? C4 N3 C6 128.1(17) . . ? N3 C4 C5 110.3(16) . . ? N3 C4 H4 124.9 . . ? C5 C4 H4 124.9 . . ? N1 C5 C4 104.6(17) . . ? N1 C5 H5 127.7 . . ? C4 C5 H5 127.7 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8 110.0(13) . . ? N1 C7 H7A 109.7 . . ? C8 C7 H7A 109.7 . . ? N1 C7 H7B 109.7 . . ? C8 C7 H7B 109.7 . . ? H7A C7 H7B 108.2 . . ? C7 C8 C9B 107.7(16) . . ? C7 C8 C9A 106.0(14) . . ? C7 C8 H8A 110.5 . . ? C9A C8 H8A 110.5 . . ? C7 C8 H8B 110.5 . . ? C9A C8 H8B 110.5 . . ? H8A C8 H8B 108.7 . . ? C7 C8 H8C 110.2 . . ? C9B C8 H8C 110.2 . . ? C7 C8 H8D 110.2 . . ? C9B C8 H8D 110.2 . . ? H8C C8 H8D 108.5 . . ? C10A C9A C8 107.5(18) . . ? C10A C9A H9A 110.2 . . ? C8 C9A H9A 110.2 . . ? C10A C9A H9B 110.2 . . ? C8 C9A H9B 110.2 . . ? H9A C9A H9B 108.5 . . ? C9A C10A H10A 109.5 . . ? C9A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C10B C9B C8 107.5(19) . . ? C10B C9B H9C 110.2 . . ? C8 C9B H9C 110.2 . . ? C10B C9B H9D 110.2 . . ? C8 C9B H9D 110.2 . . ? H9C C9B H9D 108.5 . . ? C9B C10B H10D 109.5 . . ? C9B C10B H10E 109.5 . . ? H10D C10B H10E 109.5 . . ? C9B C10B H10F 109.5 . . ? H10D C10B H10F 109.5 . . ? H10E C10B H10F 109.5 . . ? C12 N11 C15 109.0(12) . . ? C12 N11 C17 124.8(17) . . ? C15 N11 C17 126.1(18) . . ? N11 C12 N13 110.1(14) . . ? N11 C12 H12 125.0 . . ? N13 C12 H12 125.0 . . ? C12 N13 C14 105.1(14) . . ? C12 N13 C16 127.6(16) . . ? C14 N13 C16 127.2(16) . . ? C15 C14 N13 109.7(16) . . ? C15 C14 H14 125.1 . . ? N13 C14 H14 125.1 . . ? C14 C15 N11 106.0(16) . . ? C14 C15 H15 127.0 . . ? N11 C15 H15 127.0 . . ? N13 C16 H16A 109.5 . . ? N13 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N13 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N11 109.8(14) . . ? C18 C17 H17A 109.7 . . ? N11 C17 H17A 109.7 . . ? C18 C17 H17B 109.7 . . ? N11 C17 H17B 109.7 . . ? H17A C17 H17B 108.2 . . ? C17 C18 C19 107.9(15) . . ? C17 C18 H18A 110.1 . . ? C19 C18 H18A 110.1 . . ? C17 C18 H18B 110.1 . . ? C19 C18 H18B 110.1 . . ? H18A C18 H18B 108.4 . . ? C20B C19 C18 112(3) . . ? C20A C19 C18 106.3(19) . . ? C20A C19 H19A 110.5 . . ? C18 C19 H19A 110.5 . . ? C20A C19 H19B 110.5 . . ? C18 C19 H19B 110.5 . . ? H19A C19 H19B 108.7 . . ? C20B C19 H19C 109.3 . . ? C18 C19 H19C 109.3 . . ? C20B C19 H19D 109.3 . . ? C18 C19 H19D 109.3 . . ? H19C C19 H19D 108.0 . . ? C19 C20A H20A 109.5 . . ? C19 C20A H20B 109.5 . . ? H20A C20A H20B 109.5 . . ? C19 C20A H20C 109.5 . . ? H20A C20A H20C 109.5 . . ? H20B C20A H20C 109.5 . . ? C19 C20B H20D 109.5 . . ? C19 C20B H20E 109.5 . . ? H20D C20B H20E 109.5 . . ? C19 C20B H20F 109.5 . . ? H20D C20B H20F 109.5 . . ? H20E C20B H20F 109.5 . . ? 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 C5 N1 C2 N3 -6(2) . . . . ? C7 N1 C2 N3 175.4(15) . . . . ? N1 C2 N3 C4 3(2) . . . . ? N1 C2 N3 C6 -173.5(17) . . . . ? C2 N3 C4 C5 1(3) . . . . ? C6 N3 C4 C5 177.8(18) . . . . ? C2 N1 C5 C4 7(2) . . . . ? C7 N1 C5 C4 -174.9(18) . . . . ? N3 C4 C5 N1 -5(3) . . . . ? C2 N1 C7 C8 103(3) . . . . ? C5 N1 C7 C8 -75(3) . . . . ? N1 C7 C8 C9B -164(3) . . . . ? N1 C7 C8 C9A 168(2) . . . . ? C7 C8 C9A C10A 166(3) . . . . ? C9B C8 C9A C10A 68(4) . . . . ? C7 C8 C9B C10B -135(3) . . . . ? C9A C8 C9B C10B -45(4) . . . . ? C15 N11 C12 N13 0(2) . . . . ? C17 N11 C12 N13 176.6(16) . . . . ? N11 C12 N13 C14 -1(2) . . . . ? N11 C12 N13 C16 177.7(18) . . . . ? C12 N13 C14 C15 1(3) . . . . ? C16 N13 C14 C15 -177.1(19) . . . . ? N13 C14 C15 N11 -2(3) . . . . ? C12 N11 C15 C14 1(2) . . . . ? C17 N11 C15 C14 -175.6(18) . . . . ? C12 N11 C17 C18 107(2) . . . . ? C15 N11 C17 C18 -77(3) . . . . ? N11 C17 C18 C19 168(2) . . . . ? C17 C18 C19 C20B -122(4) . . . . ? C17 C18 C19 C20A -178(3) . . . . ? _diffrn_measured_fraction_theta_max 0.515 _diffrn_reflns_theta_full 14.91 _diffrn_measured_fraction_theta_full 0.515 _refine_diff_density_max 0.178 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.038 data_gamma_bmim_PF6_263K _database_code_depnum_ccdc_archive 'CCDC 909175' _refine_special_details ; The Following ALERTS were generated by PLATON checkcif PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings Differ ? The one given is more meaningful. PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced .......... ? PLAT156_ALERT_4_C Axial System Input Cell not Standard ........... ? PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C8 H15 N2 For the puropose of structure comparison the same coordinates for the structure published at 193 K were taken (CSD MAXZOB01). PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for P1 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.0050 Ang Noted, no action taken. There is evidence of disorder in this 263 K structure. ; _audit_creation_method SHELXL-97 _chemical_formula_moiety 'C8 H15 N2, P F6' _chemical_formula_sum 'C8 H15 F6 N2 P' _chemical_formula_weight 284.19 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 Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8215(8) _cell_length_b 9.0796(9) _cell_length_c 9.0381(8) _cell_angle_alpha 96.671(7) _cell_angle_beta 114.768(6) _cell_angle_gamma 103.071(7) _cell_volume 621.82(10) _cell_formula_units_Z 2 _cell_measurement_temperature 263(2) _cell_measurement_reflns_used 2522 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 23.84 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.518 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'based on symmetry-related measuraments' # SADABS V.2008/1 # The following data are from Sadabs: _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 263(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 'Bruker AXS APEX II' _diffrn_measurement_device_type Area _diffrn_measurement_method '\f & \w scans' _diffrn_reflns_number 7824 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 25.45 _reflns_number_total 2291 _reflns_number_gt 1624 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'known fractional coordinates, MAXZOB01' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008), SHELXLE' _computing_publication_material 'PLATON, XCIF, ENCIFER, SHELXLE' _computing_molecular_graphics MERCURY _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^)+(0.0585P)^2^+0.5199P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary mixed #known fractional coordinates, MAXZOB01, and difference maps _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 2291 _refine_ls_number_parameters 174 _refine_ls_number_restraints 57 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0503 _refine_ls_wR_factor_ref 0.1448 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.038 _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 0.68718(10) 0.29142(10) 0.44934(10) 0.0517(3) Uani 1 1 d . . . F1 F 0.6337(3) 0.2813(4) 0.5928(3) 0.1085(9) Uani 1 1 d . . . F2 F 0.5197(3) 0.1522(3) 0.3227(3) 0.0990(8) Uani 1 1 d . . . F3 F 0.7436(4) 0.3105(4) 0.3063(3) 0.1128(10) Uani 1 1 d . . . F4 F 0.7983(3) 0.1755(3) 0.5062(3) 0.0956(8) Uani 1 1 d . . . F5 F 0.8561(3) 0.4334(2) 0.5732(3) 0.0814(7) Uani 1 1 d . . . F6 F 0.5794(3) 0.4087(3) 0.3900(3) 0.0915(7) Uani 1 1 d . . . N1 N 1.2902(3) 0.3359(3) 0.8958(3) 0.0480(6) Uani 1 1 d . A . C2 C 1.2115(4) 0.3318(4) 0.7339(4) 0.0490(7) Uani 1 1 d . . . H2 H 1.1381 0.3902 0.6852 0.059 Uiso 1 1 calc R . . N3 N 1.2542(3) 0.2313(3) 0.6527(3) 0.0492(6) Uani 1 1 d . . . C4 C 1.3638(4) 0.1687(4) 0.7659(4) 0.0559(8) Uani 1 1 d . . . H4 H 1.4142 0.0954 0.7426 0.067 Uiso 1 1 calc R . . C5 C 1.3849(4) 0.2331(4) 0.9169(4) 0.0563(8) Uani 1 1 d . . . H5 H 1.4520 0.2116 1.0181 0.068 Uiso 1 1 calc R . . C6 C 1.1947(5) 0.1964(5) 0.4706(4) 0.0716(10) Uani 1 1 d . . . H6A H 1.1843 0.0898 0.4319 0.107 Uiso 1 1 calc R . . H6B H 1.2782 0.2634 0.4466 0.107 Uiso 1 1 calc R . . H6C H 1.0828 0.2131 0.4144 0.107 Uiso 1 1 calc R . . C7 C 1.2668(5) 0.4262(4) 1.0271(4) 0.0628(9) Uani 1 1 d U . . H7A H 1.2154 0.5056 0.9843 0.075 Uiso 0.921(8) 1 calc PR A 1 H7B H 1.3804 0.4780 1.1229 0.075 Uiso 0.921(8) 1 calc PR A 1 H7C H 1.2938 0.5348 1.0230 0.075 Uiso 0.079(8) 1 calc PR A 2 H7D H 1.3495 0.4190 1.1360 0.075 Uiso 0.079(8) 1 calc PR A 2 C8A C 1.1509(5) 0.3238(5) 1.0822(5) 0.0548(11) Uani 0.921(8) 1 d PDU A 1 H8A H 1.1428 0.3875 1.1710 0.066 Uiso 0.921(8) 1 calc PR A 1 H8B H 1.2059 0.2477 1.1291 0.066 Uiso 0.921(8) 1 calc PR A 1 C9A C 0.9683(5) 0.2390(6) 0.9455(5) 0.0594(12) Uani 0.921(8) 1 d PDU A 1 H9A H 0.9752 0.1697 0.8600 0.071 Uiso 0.921(8) 1 calc PR A 1 H9B H 0.9150 0.3142 0.8938 0.071 Uiso 0.921(8) 1 calc PR A 1 C8B C 1.086(6) 0.372(4) 1.010(5) 0.043(7) Uani 0.079(8) 1 d PDU A 2 H8C H 1.0057 0.3923 0.9071 0.051 Uiso 0.079(8) 1 calc PR A 2 H8D H 1.0824 0.4337 1.1025 0.051 Uiso 0.079(8) 1 calc PR A 2 C9B C 1.021(7) 0.203(4) 1.005(7) 0.050(8) Uani 0.079(8) 1 d PDU A 2 H9C H 1.0130 0.1425 0.9047 0.060 Uiso 0.079(8) 1 calc PR A 2 H9D H 1.1104 0.1810 1.1004 0.060 Uiso 0.079(8) 1 calc PR A 2 C10 C 0.8526(5) 0.1454(5) 1.0077(5) 0.0782(11) Uani 1 1 d D . . H10A H 0.8289 0.2147 1.0780 0.094 Uiso 0.921(8) 1 calc PR A 1 H10B H 0.9110 0.0795 1.0709 0.094 Uiso 0.921(8) 1 calc PR A 1 H10C H 0.7443 0.0824 0.9137 0.094 Uiso 0.921(8) 1 calc PR A 1 H10D H 0.8370 0.2261 1.0734 0.094 Uiso 0.079(8) 1 calc PR A 2 H10E H 0.8519 0.0568 1.0563 0.094 Uiso 0.079(8) 1 calc PR A 2 H10F H 0.7589 0.1157 0.8951 0.094 Uiso 0.079(8) 1 calc PR 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 0.0486(5) 0.0589(5) 0.0422(4) 0.0080(4) 0.0158(4) 0.0188(4) F1 0.0978(18) 0.164(3) 0.0758(15) 0.0386(16) 0.0534(14) 0.0293(18) F2 0.0685(14) 0.0720(15) 0.0969(17) -0.0059(13) -0.0025(13) 0.0074(12) F3 0.128(2) 0.158(3) 0.0750(15) 0.0225(16) 0.0669(16) 0.046(2) F4 0.0799(15) 0.0696(14) 0.1050(17) 0.0100(13) 0.0084(13) 0.0378(12) F5 0.0581(12) 0.0727(14) 0.0861(15) -0.0090(12) 0.0185(11) 0.0135(11) F6 0.0787(15) 0.0894(16) 0.1000(17) 0.0281(14) 0.0226(13) 0.0485(13) N1 0.0497(14) 0.0492(15) 0.0460(14) 0.0117(11) 0.0234(12) 0.0140(12) C2 0.0481(17) 0.0554(19) 0.0533(18) 0.0231(15) 0.0253(15) 0.0243(14) N3 0.0485(14) 0.0581(16) 0.0448(13) 0.0162(12) 0.0226(12) 0.0188(12) C4 0.0555(19) 0.057(2) 0.0584(19) 0.0176(16) 0.0237(16) 0.0270(16) C5 0.0568(19) 0.060(2) 0.0510(18) 0.0224(16) 0.0183(15) 0.0246(16) C6 0.084(3) 0.092(3) 0.0441(18) 0.0176(18) 0.0301(18) 0.034(2) C7 0.076(2) 0.0518(19) 0.0571(19) 0.0016(16) 0.0339(18) 0.0139(17) C8A 0.067(2) 0.059(2) 0.041(2) 0.0049(18) 0.0281(18) 0.021(2) C9A 0.059(2) 0.075(3) 0.045(2) 0.010(2) 0.0230(19) 0.025(2) C8B 0.065(11) 0.051(13) 0.023(13) 0.010(12) 0.019(12) 0.039(12) C9B 0.053(17) 0.055(14) 0.051(19) 0.020(15) 0.022(14) 0.031(11) C10 0.065(2) 0.090(3) 0.079(3) 0.012(2) 0.036(2) 0.020(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 P1 F1 1.560(2) . ? P1 F6 1.577(2) . ? P1 F2 1.579(2) . ? P1 F4 1.582(2) . ? P1 F3 1.582(2) . ? P1 F5 1.592(2) . ? N1 C2 1.322(4) . ? N1 C5 1.367(4) . ? N1 C7 1.475(4) . ? C2 N3 1.321(4) . ? C2 H2 0.9300 . ? N3 C4 1.364(4) . ? N3 C6 1.471(4) . ? C4 C5 1.338(4) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 C8B 1.49(4) . ? C7 C8A 1.505(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C7 H7C 0.9700 . ? C7 H7D 0.9700 . ? C8A C9A 1.505(5) . ? C8A H8A 0.9700 . ? C8A H8B 0.9700 . ? C9A C10 1.510(5) . ? C9A H9A 0.9700 . ? C9A H9B 0.9700 . ? C8B C9B 1.50(2) . ? C8B H8C 0.9700 . ? C8B H8D 0.9700 . ? C9B C10 1.47(5) . ? C9B H9C 0.9700 . ? C9B H9D 0.9700 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C10 H10D 0.9600 . ? C10 H10E 0.9600 . ? C10 H10F 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 P1 F6 90.13(15) . . ? F1 P1 F2 91.93(16) . . ? F6 P1 F2 89.28(13) . . ? F1 P1 F4 91.37(16) . . ? F6 P1 F4 178.40(15) . . ? F2 P1 F4 91.23(13) . . ? F1 P1 F3 177.24(17) . . ? F6 P1 F3 87.97(15) . . ? F2 P1 F3 90.05(15) . . ? F4 P1 F3 90.52(16) . . ? F1 P1 F5 89.35(14) . . ? F6 P1 F5 90.08(13) . . ? F2 P1 F5 178.58(14) . . ? F4 P1 F5 89.38(12) . . ? F3 P1 F5 88.66(15) . . ? C2 N1 C5 107.8(3) . . ? C2 N1 C7 125.5(3) . . ? C5 N1 C7 126.5(3) . . ? N3 C2 N1 108.9(3) . . ? N3 C2 H2 125.5 . . ? N1 C2 H2 125.5 . . ? C2 N3 C4 108.6(3) . . ? C2 N3 C6 125.1(3) . . ? C4 N3 C6 126.3(3) . . ? C5 C4 N3 106.8(3) . . ? C5 C4 H4 126.6 . . ? N3 C4 H4 126.6 . . ? C4 C5 N1 107.8(3) . . ? C4 C5 H5 126.1 . . ? N1 C5 H5 126.1 . . ? N3 C6 H6A 109.5 . . ? N3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? N3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8B 113.4(13) . . ? N1 C7 C8A 111.7(3) . . ? N1 C7 H7A 109.3 . . ? C8A C7 H7A 109.3 . . ? N1 C7 H7B 109.3 . . ? C8A C7 H7B 109.3 . . ? H7A C7 H7B 107.9 . . ? N1 C7 H7C 108.9 . . ? C8B C7 H7C 108.9 . . ? N1 C7 H7D 108.9 . . ? C8B C7 H7D 108.9 . . ? H7C C7 H7D 107.7 . . ? C7 C8A C9A 114.7(4) . . ? C7 C8A H8A 108.6 . . ? C9A C8A H8A 108.6 . . ? C7 C8A H8B 108.6 . . ? C9A C8A H8B 108.6 . . ? H8A C8A H8B 107.6 . . ? C8A C9A C10 113.2(4) . . ? C8A C9A H9A 108.9 . . ? C10 C9A H9A 108.9 . . ? C8A C9A H9B 108.9 . . ? C10 C9A H9B 108.9 . . ? H9A C9A H9B 107.8 . . ? C7 C8B C9B 115(3) . . ? C7 C8B H8C 108.5 . . ? C9B C8B H8C 108.5 . . ? C7 C8B H8D 108.5 . . ? C9B C8B H8D 108.5 . . ? H8C C8B H8D 107.5 . . ? C10 C9B C8B 118(4) . . ? C10 C9B H9C 107.7 . . ? C8B C9B H9C 107.7 . . ? C10 C9B H9D 107.7 . . ? C8B C9B H9D 107.7 . . ? H9C C9B H9D 107.1 . . ? C9A C10 H10A 109.5 . . ? C9A C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9A C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9B C10 H10D 109.5 . . ? C9B C10 H10E 109.5 . . ? H10D C10 H10E 109.5 . . ? C9B C10 H10F 109.5 . . ? H10A C10 H10F 109.9 . . ? H10D C10 H10F 109.5 . . ? H10E C10 H10F 109.5 . . ? 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 C5 N1 C2 N3 -0.5(3) . . . . ? C7 N1 C2 N3 -175.8(3) . . . . ? N1 C2 N3 C4 0.0(3) . . . . ? N1 C2 N3 C6 -178.9(3) . . . . ? C2 N3 C4 C5 0.5(4) . . . . ? C6 N3 C4 C5 179.4(3) . . . . ? N3 C4 C5 N1 -0.8(4) . . . . ? C2 N1 C5 C4 0.8(4) . . . . ? C7 N1 C5 C4 176.0(3) . . . . ? C2 N1 C7 C8B 65.4(17) . . . . ? C5 N1 C7 C8B -109.0(17) . . . . ? C2 N1 C7 C8A 103.5(4) . . . . ? C5 N1 C7 C8A -71.0(4) . . . . ? N1 C7 C8A C9A -60.3(5) . . . . ? C8B C7 C8A C9A 40(2) . . . . ? C7 C8A C9A C10 -176.4(3) . . . . ? N1 C7 C8B C9B 56(4) . . . . ? C8A C7 C8B C9B -39(3) . . . . ? C7 C8B C9B C10 173(3) . . . . ? C8B C9B C10 C9A 45(3) . . . . ? C8A C9A C10 C9B -41(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.45 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.424 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.049 #===END