# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/256 data_eriklsx _audit_creation_method SHELXL _chemical_name_systematic ; Nitrozonium hexafluorophosphate/p-nitrosoanisol/toluene molecular complex 1:1:1 ; _chemical_name_common ? _chemical_formula_moiety ; (N O)^+^, (F6 P)^-^, (C7 H7 N O2), (C7 H8) ; _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H15 F6 N2 O3 P' _chemical_formula_weight 404.25 _chemical_melting_point ? _chemical_compound_source 'chemical synthesis' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'F' 'F' 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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 7.5078(6) _cell_length_b 10.7748(9) _cell_length_c 11.3584(9) _cell_angle_alpha 89.381(2) _cell_angle_beta 72.055(2) _cell_angle_gamma 79.252(2) _cell_volume 857.73(12) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2009 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 32.0 _exptl_crystal_description 'plate' _exptl_crystal_colour 'brown' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.565 _exptl_crystal_density_method none _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_type 'Semi-empirical (SADABS procedure)' _exptl_absorpt_correction_T_min 0.879 _exptl_absorpt_correction_T_max 0.928 _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART' _diffrn_measurement_method ; \w-scan, frame range 0.3 deg, hemisphere ; _diffrn_standards_number 95 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 3.8 _diffrn_reflns_number 7704 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 28.00 _reflns_number_total 4084 _reflns_number_observed 2613 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'SMART V4.050 (Siemens, 1989-95)' _computing_cell_refinement 'SAINT V4.050 (Siemens, 1989-95)' _computing_data_reduction 'SAINT & SADABS (Sheldrick, 1996)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'XP V5.06 (Siemens, 1996)' _computing_publication_material 'SHELXL-93 & XCIF V5.05 (Siemens, 1996)' _refine_special_details ; Refinement on F^2^ for all reflections except for 339 with very negative F^2^. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+2.0700P] 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 ; riding and rotating (for Me-hydrogens) model with Uiso=1.2Uiso/eq of an adjacent atom (1.5Uiso/eq for Me-hydrogens) ; _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3745 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1354 _refine_ls_R_factor_obs 0.0772 _refine_ls_wR_factor_all 0.1728 _refine_ls_wR_factor_obs 0.1390 _refine_ls_goodness_of_fit_all 1.110 _refine_ls_goodness_of_fit_obs 1.205 _refine_ls_restrained_S_all 1.183 _refine_ls_restrained_S_obs 1.205 _refine_ls_shift/esd_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 P1 P 0.48582(14) 0.16897(9) 0.77587(10) 0.0227(2) Uani 1 d . . F1 F 0.4759(3) 0.2486(2) 0.8966(2) 0.0427(7) Uani 1 d . . F2 F 0.4968(4) 0.0899(2) 0.6549(2) 0.0441(7) Uani 1 d . . F3 F 0.3208(4) 0.0994(3) 0.8558(3) 0.0503(7) Uani 1 d . . F4 F 0.3283(4) 0.2771(2) 0.7522(3) 0.0567(8) Uani 1 d . . F5 F 0.6398(4) 0.0592(2) 0.8025(3) 0.0548(8) Uani 1 d . . F6 F 0.6511(4) 0.2377(3) 0.6978(3) 0.0584(8) Uani 1 d . . C1 C 0.0939(5) 0.8026(4) 0.7085(4) 0.0253(8) Uani 1 d . . C2 C 0.1995(5) 0.6923(4) 0.6403(3) 0.0243(8) Uani 1 d . . H2 H 0.2847(5) 0.6976(4) 0.5597(3) 0.029 Uiso 1 calc R . C3 C 0.1822(5) 0.5746(4) 0.6882(4) 0.0280(9) Uani 1 d . . H3 H 0.2572(5) 0.5003(4) 0.6408(4) 0.034 Uiso 1 calc R . C4 C 0.0563(5) 0.5649(4) 0.8044(4) 0.0286(9) Uani 1 d . . H4 H 0.0441(5) 0.4842(4) 0.8370(4) 0.034 Uiso 1 calc R . C5 C -0.0513(5) 0.6733(4) 0.8726(4) 0.0302(9) Uani 1 d . . H5 H -0.1385(5) 0.6671(4) 0.9523(4) 0.036 Uiso 1 calc R . C6 C -0.0335(5) 0.7919(4) 0.8259(4) 0.0277(8) Uani 1 d . . H6 H -0.1083(5) 0.8659(4) 0.8739(4) 0.033 Uiso 1 calc R . C7 C 0.1159(6) 0.9312(4) 0.6579(4) 0.0347(10) Uani 1 d . . H7A H -0.0088(9) 0.9789(11) 0.6580(25) 0.052 Uiso 1 calc R . H7B H 0.2036(32) 0.9207(4) 0.5729(10) 0.052 Uiso 1 calc R . H7C H 0.1672(39) 0.9772(11) 0.7099(16) 0.052 Uiso 1 calc R . C11 C -0.7336(5) 0.3361(3) 1.3904(3) 0.0200(7) Uani 1 d . . C12 C -0.6350(5) 0.2199(3) 1.3271(3) 0.0235(8) Uani 1 d . . H12A H -0.6600(5) 0.1426(3) 1.3634(3) 0.028 Uiso 1 calc R . C13 C -0.5034(5) 0.2190(3) 1.2133(3) 0.0223(8) Uani 1 d . . H13A H -0.4367(5) 0.1413(3) 1.1689(3) 0.027 Uiso 1 calc R . C14 C -0.4673(5) 0.3370(3) 1.1618(3) 0.0210(7) Uani 1 d . . C15 C -0.5675(5) 0.4534(3) 1.2257(3) 0.0223(8) Uani 1 d . . H15A H -0.5436(5) 0.5310(3) 1.1898(3) 0.027 Uiso 1 calc R . C16 C -0.6977(5) 0.4528(3) 1.3383(3) 0.0223(8) Uani 1 d . . H16A H -0.7653(5) 0.5303(3) 1.3826(3) 0.027 Uiso 1 calc R . C17 C -0.9040(6) 0.2323(4) 1.5641(4) 0.0311(9) Uani 1 d . . H17A H -1.0000(29) 0.2551(4) 1.6453(11) 0.047 Uiso 1 calc R . H17B H -0.7872(10) 0.1828(13) 1.5750(23) 0.047 Uiso 1 calc R . H17C H -0.9531(37) 0.1819(13) 1.5143(13) 0.047 Uiso 1 calc R . N1 N -0.3328(4) 0.3299(3) 1.0496(3) 0.0239(7) Uani 1 d . . N2 N -0.1736(5) 0.1744(4) 0.9637(3) 0.0385(9) Uani 1 d . . O1 O -0.2851(4) 0.4174(3) 0.9879(2) 0.0332(7) Uani 1 d . . O2 O -0.0867(4) 0.2134(3) 0.8778(3) 0.0413(8) Uani 1 d . . O3 O -0.8622(4) 0.3467(2) 1.5012(2) 0.0269(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 P1 0.0187(5) 0.0186(5) 0.0311(5) -0.0027(4) -0.0081(4) -0.0036(4) F1 0.0391(14) 0.048(2) 0.0437(14) -0.0190(12) -0.0158(12) -0.0095(12) F2 0.053(2) 0.0373(14) 0.0410(14) -0.0148(12) -0.0150(12) -0.0040(12) F3 0.042(2) 0.050(2) 0.058(2) -0.0028(14) -0.0031(13) -0.0255(13) F4 0.064(2) 0.0305(14) 0.085(2) -0.0069(14) -0.049(2) 0.0123(13) F5 0.047(2) 0.036(2) 0.087(2) -0.0069(15) -0.041(2) 0.0116(13) F6 0.053(2) 0.054(2) 0.060(2) -0.0052(14) 0.0105(14) -0.0355(15) C1 0.025(2) 0.028(2) 0.032(2) 0.006(2) -0.020(2) -0.007(2) C2 0.018(2) 0.031(2) 0.025(2) 0.001(2) -0.0076(15) -0.008(2) C3 0.030(2) 0.023(2) 0.034(2) -0.001(2) -0.015(2) -0.005(2) C4 0.030(2) 0.026(2) 0.039(2) 0.005(2) -0.021(2) -0.010(2) C5 0.019(2) 0.045(3) 0.028(2) 0.008(2) -0.007(2) -0.010(2) C6 0.021(2) 0.033(2) 0.028(2) -0.005(2) -0.009(2) -0.001(2) C7 0.037(2) 0.029(2) 0.042(2) 0.004(2) -0.017(2) -0.009(2) C11 0.018(2) 0.025(2) 0.020(2) 0.0012(14) -0.0107(14) -0.0048(14) C12 0.025(2) 0.022(2) 0.026(2) 0.000(2) -0.008(2) -0.010(2) C13 0.024(2) 0.016(2) 0.030(2) -0.0042(15) -0.012(2) -0.0031(14) C14 0.020(2) 0.025(2) 0.021(2) 0.0022(15) -0.0090(14) -0.0071(15) C15 0.027(2) 0.018(2) 0.027(2) 0.0072(15) -0.015(2) -0.0065(15) C16 0.024(2) 0.018(2) 0.027(2) -0.0029(15) -0.011(2) -0.0028(15) C17 0.032(2) 0.036(2) 0.027(2) 0.012(2) -0.008(2) -0.013(2) N1 0.021(2) 0.034(2) 0.022(2) 0.0032(14) -0.0116(13) -0.0092(14) N2 0.033(2) 0.048(2) 0.034(2) -0.007(2) -0.011(2) -0.003(2) O1 0.0311(15) 0.048(2) 0.0262(14) 0.0153(13) -0.0114(12) -0.0179(14) O2 0.028(2) 0.068(2) 0.025(2) -0.0085(15) -0.0050(13) -0.007(2) O3 0.0261(14) 0.0311(15) 0.0227(13) 0.0007(11) -0.0068(11) -0.0054(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 F4 1.582(3) . ? P1 F5 1.589(3) . ? P1 F6 1.589(3) . ? P1 F2 1.598(3) . ? P1 F3 1.600(3) . ? P1 F1 1.600(2) . ? C1 C2 1.389(5) . ? C1 C6 1.400(5) . ? C1 C7 1.512(5) . ? C2 C3 1.387(5) . ? C3 C4 1.383(6) . ? C4 C5 1.378(6) . ? C5 C6 1.391(6) . ? C11 O3 1.320(4) . ? C11 C12 1.407(5) . ? C11 C16 1.420(5) . ? C12 C13 1.362(5) . ? C13 C14 1.431(5) . ? C14 N1 1.353(5) . ? C14 C15 1.413(5) . ? C15 C16 1.351(5) . ? C17 O3 1.454(5) . ? N1 O1 1.211(4) . ? N1 N2 1.938(5) . ? N2 O2 1.120(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 F4 P1 F5 178.5(2) . . ? F4 P1 F6 91.2(2) . . ? F5 P1 F6 90.2(2) . . ? F4 P1 F2 90.82(15) . . ? F5 P1 F2 89.58(15) . . ? F6 P1 F2 91.1(2) . . ? F4 P1 F3 89.3(2) . . ? F5 P1 F3 89.2(2) . . ? F6 P1 F3 179.2(2) . . ? F2 P1 F3 89.45(15) . . ? F4 P1 F1 89.20(15) . . ? F5 P1 F1 90.41(15) . . ? F6 P1 F1 88.59(15) . . ? F2 P1 F1 179.6(2) . . ? F3 P1 F1 90.90(15) . . ? C2 C1 C6 118.3(4) . . ? C2 C1 C7 121.1(4) . . ? C6 C1 C7 120.6(4) . . ? C3 C2 C1 121.0(4) . . ? C4 C3 C2 120.4(4) . . ? C5 C4 C3 119.4(4) . . ? C4 C5 C6 120.7(4) . . ? C5 C6 C1 120.3(4) . . ? O3 C11 C12 124.0(3) . . ? O3 C11 C16 114.8(3) . . ? C12 C11 C16 121.2(3) . . ? C13 C12 C11 119.6(3) . . ? C12 C13 C14 118.8(3) . . ? N1 C14 C15 122.6(3) . . ? N1 C14 C13 116.1(3) . . ? C15 C14 C13 121.3(3) . . ? C16 C15 C14 119.2(3) . . ? C15 C16 C11 119.9(3) . . ? O1 N1 C14 127.0(3) . . ? O1 N1 N2 108.2(3) . . ? C14 N1 N2 124.8(3) . . ? O2 N2 N1 100.0(3) . . ? C11 O3 C17 118.9(3) . . ? _refine_diff_density_max 0.473 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.081