Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2002 data_ph3cnf2 _database_code_CSD 188416 _journal_coden_Cambridge 182 loop_ _publ_author_name 'Prakash, G. K. Surya' 'Christe, Karl O.' 'Etzkorn, Markus' 'Olah, G. A.' 'Schneider, Stefan' 'Vij, Ashwani' _publ_contact_author_name 'Dr G K Surya Prakash' _publ_contact_author_address ; Department of Chemistry University of Southern California Loker Hydrocarbon Research Institut University Park Los Angeles California CA-90089 1661 UNITED STATES OF AMERICA ; _publ_contact_author_email 'GPRAKASH@USC.EDU' _publ_requested_journal 'Chemical Communications' _publ_section_title ; Triphenylmethyldifluoramine: A Stable Reagent for the Synthesis of gem-Bis(difluoramines) ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Trityl difluoroamine' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H15 F2 N' _chemical_formula_weight 295.32 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.3882(12) _cell_length_b 9.8259(11) _cell_length_c 14.6065(16) _cell_angle_alpha 90.00 _cell_angle_beta 92.402(2) _cell_angle_gamma 90.00 _cell_volume 1489.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 213(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description chunk _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.317 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type "SADABS" _exptl_absorpt_correction_T_min 0.9536 _exptl_absorpt_correction_T_max 0.9732 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 213(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_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number '50 frames' _diffrn_standards_interval_count 'start and end of data collection' _diffrn_standards_interval_time ? _diffrn_standards_decay_% < 1% _diffrn_reflns_number 9649 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 26.37 _reflns_number_total 3035 _reflns_number_gt 2483 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0573P)^2^+0.2967P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0090(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3035 _refine_ls_number_parameters 260 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0378 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.1020 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 F1 F 0.41696(8) 0.59111(10) 0.10606(6) 0.0537(3) Uani 1 1 d . . . F2 F 0.54761(8) 0.45119(8) 0.17588(6) 0.0508(3) Uani 1 1 d . . . N1 N 0.47959(11) 0.57225(12) 0.19250(8) 0.0380(3) Uani 1 1 d . . . C1 C 0.58051(11) 0.68402(12) 0.20389(8) 0.0288(3) Uani 1 1 d . . . C2 C 0.68992(11) 0.66935(12) 0.13705(8) 0.0298(3) Uani 1 1 d . . . C3 C 0.66336(14) 0.66832(14) 0.04245(9) 0.0381(3) Uani 1 1 d . . . H3 H 0.5756(16) 0.6751(15) 0.0187(10) 0.042(4) Uiso 1 1 d . . . C4 C 0.76214(16) 0.65771(15) -0.01797(10) 0.0453(4) Uani 1 1 d . . . H4 H 0.7380(16) 0.6535(17) -0.0830(12) 0.055(5) Uiso 1 1 d . . . C5 C 0.88874(15) 0.65055(16) 0.01395(11) 0.0488(4) Uani 1 1 d . . . H5 H 0.9577(17) 0.6451(18) -0.0296(12) 0.057(5) Uiso 1 1 d . . . C6 C 0.91610(15) 0.65135(17) 0.10679(12) 0.0492(4) Uani 1 1 d . . . H6 H 1.0006(19) 0.6462(18) 0.1308(13) 0.064(5) Uiso 1 1 d . . . C7 C 0.81765(13) 0.65949(14) 0.16822(10) 0.0379(3) Uani 1 1 d . . . H7 H 0.8403(14) 0.6603(15) 0.2325(11) 0.038(4) Uiso 1 1 d . . . C8 C 0.50372(12) 0.81656(13) 0.19093(8) 0.0313(3) Uani 1 1 d . . . C9 C 0.39283(14) 0.83443(18) 0.23961(10) 0.0466(4) Uani 1 1 d . . . H9 H 0.3669(15) 0.7623(17) 0.2774(11) 0.048(4) Uiso 1 1 d . . . C10 C 0.32279(17) 0.9534(2) 0.23130(12) 0.0633(5) Uani 1 1 d . . . H10 H 0.247(2) 0.962(2) 0.2632(14) 0.078(6) Uiso 1 1 d . . . C11 C 0.36363(19) 1.05672(19) 0.17603(12) 0.0619(5) Uani 1 1 d . . . H11 H 0.322(2) 1.143(2) 0.1743(15) 0.084(6) Uiso 1 1 d . . . C12 C 0.47444(16) 1.04213(16) 0.12898(11) 0.0496(4) Uani 1 1 d . . . H12 H 0.5025(17) 1.1157(19) 0.0908(12) 0.058(5) Uiso 1 1 d . . . C13 C 0.54411(13) 0.92178(13) 0.13593(9) 0.0364(3) Uani 1 1 d . . . H13 H 0.6232(15) 0.9131(15) 0.1033(10) 0.038(4) Uiso 1 1 d . . . C14 C 0.62696(11) 0.67413(12) 0.30519(8) 0.0292(3) Uani 1 1 d . . . C15 C 0.61000(13) 0.56041(15) 0.35989(10) 0.0387(3) Uani 1 1 d . . . H15 H 0.5693(15) 0.4812(17) 0.3343(11) 0.046(4) Uiso 1 1 d . . . C16 C 0.65490(15) 0.56068(17) 0.45097(10) 0.0473(4) Uani 1 1 d . . . H16 H 0.6426(16) 0.4837(19) 0.4877(12) 0.058(5) Uiso 1 1 d . . . C17 C 0.71746(15) 0.67250(17) 0.48805(10) 0.0472(4) Uani 1 1 d . . . H17 H 0.7488(17) 0.6724(17) 0.5521(13) 0.059(5) Uiso 1 1 d . . . C18 C 0.73453(15) 0.78604(16) 0.43407(10) 0.0443(4) Uani 1 1 d . . . H18 H 0.7791(16) 0.8642(18) 0.4597(12) 0.054(5) Uiso 1 1 d . . . C19 C 0.68899(13) 0.78691(14) 0.34393(9) 0.0361(3) Uani 1 1 d . . . H19 H 0.6998(14) 0.8665(16) 0.3074(11) 0.043(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0473(5) 0.0696(6) 0.0431(5) -0.0033(4) -0.0117(4) -0.0178(4) F2 0.0571(5) 0.0338(4) 0.0620(6) -0.0088(4) 0.0079(4) -0.0077(4) N1 0.0349(6) 0.0411(6) 0.0379(6) -0.0025(5) -0.0011(5) -0.0063(5) C1 0.0266(6) 0.0305(6) 0.0294(6) 0.0000(5) 0.0018(5) -0.0025(5) C2 0.0315(6) 0.0256(6) 0.0327(6) 0.0002(5) 0.0048(5) 0.0003(5) C3 0.0413(7) 0.0403(7) 0.0329(7) -0.0015(5) 0.0045(6) 0.0009(6) C4 0.0592(9) 0.0414(8) 0.0365(7) -0.0007(6) 0.0153(7) 0.0005(7) C5 0.0509(9) 0.0427(8) 0.0548(9) 0.0020(7) 0.0274(7) 0.0044(7) C6 0.0331(7) 0.0536(9) 0.0616(10) 0.0037(7) 0.0115(7) 0.0052(7) C7 0.0329(7) 0.0409(7) 0.0400(7) 0.0028(6) 0.0042(5) 0.0027(5) C8 0.0292(6) 0.0387(7) 0.0258(6) -0.0016(5) -0.0013(5) 0.0044(5) C9 0.0427(8) 0.0620(10) 0.0360(7) 0.0084(7) 0.0108(6) 0.0155(7) C10 0.0558(10) 0.0882(14) 0.0469(9) 0.0062(9) 0.0152(8) 0.0371(9) C11 0.0746(12) 0.0635(11) 0.0476(9) 0.0032(8) 0.0023(8) 0.0403(9) C12 0.0619(10) 0.0412(8) 0.0453(8) 0.0053(7) -0.0022(7) 0.0128(7) C13 0.0371(7) 0.0368(7) 0.0354(7) 0.0015(5) 0.0007(5) 0.0034(5) C14 0.0254(6) 0.0332(6) 0.0293(6) 0.0008(5) 0.0039(5) 0.0032(5) C15 0.0388(7) 0.0383(7) 0.0391(7) 0.0064(6) 0.0033(6) -0.0020(6) C16 0.0476(8) 0.0545(9) 0.0401(8) 0.0177(7) 0.0059(6) 0.0040(7) C17 0.0480(8) 0.0653(10) 0.0280(7) 0.0019(6) -0.0031(6) 0.0113(7) C18 0.0461(8) 0.0475(8) 0.0385(7) -0.0069(6) -0.0071(6) 0.0035(7) C19 0.0401(7) 0.0335(7) 0.0345(7) 0.0003(5) -0.0025(5) 0.0002(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 N1 1.4080(14) . ? F2 N1 1.4098(14) . ? N1 C1 1.5226(16) . ? C1 C8 1.5348(17) . ? C1 C2 1.5358(16) . ? C1 C14 1.5400(16) . ? C2 C7 1.3881(18) . ? C2 C3 1.3977(18) . ? C3 C4 1.3851(19) . ? C4 C5 1.379(2) . ? C5 C6 1.374(2) . ? C6 C7 1.391(2) . ? C8 C13 1.3852(18) . ? C8 C9 1.3899(18) . ? C9 C10 1.379(2) . ? C10 C11 1.375(3) . ? C11 C12 1.373(2) . ? C12 C13 1.388(2) . ? C14 C15 1.3893(18) . ? C14 C19 1.3903(18) . ? C15 C16 1.391(2) . ? C16 C17 1.376(2) . ? C17 C18 1.382(2) . ? C18 C19 1.3802(19) . ? 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 N1 F2 99.95(9) . . ? F1 N1 C1 107.05(9) . . ? F2 N1 C1 106.24(9) . . ? N1 C1 C8 104.28(9) . . ? N1 C1 C2 112.79(10) . . ? C8 C1 C2 113.32(10) . . ? N1 C1 C14 104.25(9) . . ? C8 C1 C14 108.20(9) . . ? C2 C1 C14 113.23(9) . . ? C7 C2 C3 118.04(12) . . ? C7 C2 C1 121.38(11) . . ? C3 C2 C1 120.56(11) . . ? C4 C3 C2 120.64(13) . . ? C5 C4 C3 120.68(14) . . ? C6 C5 C4 119.24(13) . . ? C5 C6 C7 120.65(14) . . ? C2 C7 C6 120.74(13) . . ? C13 C8 C9 118.69(12) . . ? C13 C8 C1 122.43(11) . . ? C9 C8 C1 118.80(12) . . ? C10 C9 C8 120.50(15) . . ? C11 C10 C9 120.17(15) . . ? C12 C11 C10 120.17(15) . . ? C11 C12 C13 119.87(15) . . ? C8 C13 C12 120.57(13) . . ? C15 C14 C19 118.35(12) . . ? C15 C14 C1 124.13(11) . . ? C19 C14 C1 117.52(11) . . ? C14 C15 C16 120.19(13) . . ? C17 C16 C15 120.78(14) . . ? C16 C17 C18 119.33(13) . . ? C19 C18 C17 120.15(14) . . ? C18 C19 C14 121.18(13) . . ? 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 F1 N1 C1 C8 56.39(11) . . . . ? F2 N1 C1 C8 162.51(9) . . . . ? F1 N1 C1 C2 -66.98(12) . . . . ? F2 N1 C1 C2 39.14(12) . . . . ? F1 N1 C1 C14 169.79(9) . . . . ? F2 N1 C1 C14 -84.09(10) . . . . ? N1 C1 C2 C7 -122.96(12) . . . . ? C8 C1 C2 C7 118.85(13) . . . . ? C14 C1 C2 C7 -4.87(16) . . . . ? N1 C1 C2 C3 58.34(15) . . . . ? C8 C1 C2 C3 -59.86(15) . . . . ? C14 C1 C2 C3 176.43(11) . . . . ? C7 C2 C3 C4 0.01(19) . . . . ? C1 C2 C3 C4 178.76(12) . . . . ? C2 C3 C4 C5 -1.2(2) . . . . ? C3 C4 C5 C6 1.3(2) . . . . ? C4 C5 C6 C7 -0.1(2) . . . . ? C3 C2 C7 C6 1.2(2) . . . . ? C1 C2 C7 C6 -177.59(13) . . . . ? C5 C6 C7 C2 -1.1(2) . . . . ? N1 C1 C8 C13 -133.84(12) . . . . ? C2 C1 C8 C13 -10.82(16) . . . . ? C14 C1 C8 C13 115.61(12) . . . . ? N1 C1 C8 C9 49.34(15) . . . . ? C2 C1 C8 C9 172.36(12) . . . . ? C14 C1 C8 C9 -61.21(15) . . . . ? C13 C8 C9 C10 1.7(2) . . . . ? C1 C8 C9 C10 178.59(14) . . . . ? C8 C9 C10 C11 -1.3(3) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C13 1.2(3) . . . . ? C9 C8 C13 C12 -0.6(2) . . . . ? C1 C8 C13 C12 -177.41(12) . . . . ? C11 C12 C13 C8 -0.8(2) . . . . ? N1 C1 C14 C15 18.95(15) . . . . ? C8 C1 C14 C15 129.53(12) . . . . ? C2 C1 C14 C15 -103.99(13) . . . . ? N1 C1 C14 C19 -160.64(11) . . . . ? C8 C1 C14 C19 -50.07(14) . . . . ? C2 C1 C14 C19 76.42(14) . . . . ? C19 C14 C15 C16 -0.22(19) . . . . ? C1 C14 C15 C16 -179.82(12) . . . . ? C14 C15 C16 C17 -0.5(2) . . . . ? C15 C16 C17 C18 0.6(2) . . . . ? C16 C17 C18 C19 0.1(2) . . . . ? C17 C18 C19 C14 -0.9(2) . . . . ? C15 C14 C19 C18 0.92(19) . . . . ? C1 C14 C19 C18 -179.46(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.300 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.035