# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Norbert Mitzel' _publ_contact_author_email MITZEL@UNI-BIELEFELD.DE _publ_section_title ; The alpha-effect in silicon chemistry studied with a series of penta-fluoro-phenylsilyl compounds with SiCN, SiNN and SiON backbones ; loop_ _publ_author_name 'Norbert Mitzel' 'Raphael J F Berger' 'Markus Woski' # Attachment 'Compounds_1_2_3.txt' data_markus23 _database_code_depnum_ccdc_archive 'CCDC 688419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C9 H8 F7 N Si' _chemical_formula_weight 291.25 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' Si Si 0.0817 0.0704 '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 5.8972(12) _cell_length_b 10.326(2) _cell_length_c 10.892(2) _cell_angle_alpha 68.54(3) _cell_angle_beta 80.39(3) _cell_angle_gamma 74.53(3) _cell_volume 593.1(2) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 4.99 _cell_measurement_theta_max 25.66 _exptl_crystal_description cylinder _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.5 _exptl_crystal_size_min 0.5 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ by the OHCD Method (according to R. Boese) ; _diffrn_ambient_temperature 233(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 'Stoe IPDS I' _diffrn_measurement_method 'phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7718 _diffrn_reflns_av_R_equivalents 0.1231 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.99 _diffrn_reflns_theta_max 25.66 _reflns_number_total 2020 _reflns_number_gt 1681 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS-1' _computing_cell_refinement 'X-AREA (STOE 2003)' _computing_data_reduction 'X-AREA (STOE 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.01' _computing_publication_material 'SHELXTL 5.01' _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^)+(0.0513P)^2^+0.9367P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2020 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0960 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.1901 _refine_ls_wR_factor_gt 0.1785 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 Si Si 0.2685(2) 0.86837(12) 0.90696(11) 0.0498(4) Uani 1 1 d . . . F3 F 0.0525(5) 0.7788(3) 0.7181(3) 0.0660(8) Uani 1 1 d . . . F4 F 0.2353(6) 0.5719(3) 0.6143(3) 0.0803(10) Uani 1 1 d . . . F7 F 0.7297(5) 0.6444(3) 0.9505(3) 0.0679(8) Uani 1 1 d . . . F5 F 0.6694(7) 0.4031(3) 0.6733(3) 0.0869(11) Uani 1 1 d . . . F2 F -0.0032(6) 0.9013(4) 0.9168(4) 0.0837(10) Uani 1 1 d . . . F1 F 0.3372(7) 0.8109(4) 1.0536(3) 0.0877(11) Uani 1 1 d . . . N N 0.3631(7) 1.0578(4) 0.6712(3) 0.0515(9) Uani 1 1 d . . . C4 C 0.3829(7) 0.7187(4) 0.8396(3) 0.0414(9) Uani 1 1 d . . . F6 F 0.9137(6) 0.4392(3) 0.8438(3) 0.0834(10) Uani 1 1 d . . . C5 C 0.2643(8) 0.6948(4) 0.7529(4) 0.0442(9) Uani 1 1 d . . . C6 C 0.3567(9) 0.5895(5) 0.6983(4) 0.0540(11) Uani 1 1 d . . . C9 C 0.6018(8) 0.6289(4) 0.8673(4) 0.0463(10) Uani 1 1 d . . . C8 C 0.7001(8) 0.5239(5) 0.8136(4) 0.0551(11) Uani 1 1 d . . . C7 C 0.5762(9) 0.5039(4) 0.7281(4) 0.0556(12) Uani 1 1 d . . . C3 C 0.4069(12) 1.0183(6) 0.8124(5) 0.0697(14) Uani 1 1 d . . . H3A H 0.3386 1.0986 0.8431 0.084 Uiso 1 1 calc R . . H3B H 0.5750 0.9908 0.8228 0.084 Uiso 1 1 calc R . . C2 C 0.5698(15) 1.1009(9) 0.5919(8) 0.108(2) Uani 1 1 d . . . H2A H 0.5519 1.1208 0.5004 0.162 Uiso 1 1 calc R . . H2B H 0.7067 1.0255 0.6191 0.162 Uiso 1 1 calc R . . H2C H 0.5883 1.1852 0.6036 0.162 Uiso 1 1 calc R . . C1 C 0.1585(17) 1.1690(9) 0.6352(12) 0.148(4) Uani 1 1 d . . . H1B H 0.1402 1.1939 0.5428 0.222 Uiso 1 1 calc R . . H1A H 0.1748 1.2511 0.6519 0.222 Uiso 1 1 calc R . . H1C H 0.0223 1.1373 0.6865 0.222 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 Si 0.0699(9) 0.0473(6) 0.0391(6) -0.0184(5) -0.0004(5) -0.0211(5) F3 0.0589(19) 0.0772(18) 0.0627(16) -0.0226(13) -0.0243(13) -0.0063(13) F4 0.120(3) 0.089(2) 0.0526(15) -0.0318(14) -0.0242(16) -0.0354(18) F7 0.0638(19) 0.0812(19) 0.0664(17) -0.0208(14) -0.0237(13) -0.0237(14) F5 0.133(3) 0.0635(17) 0.0605(17) -0.0356(14) 0.0071(17) -0.0049(17) F2 0.060(2) 0.083(2) 0.127(3) -0.065(2) 0.0077(17) -0.0131(15) F1 0.134(3) 0.089(2) 0.0495(16) -0.0355(15) -0.0167(17) -0.0174(19) N 0.064(3) 0.0421(18) 0.0474(19) -0.0079(14) -0.0028(16) -0.0211(16) C4 0.050(3) 0.045(2) 0.0314(17) -0.0108(15) -0.0008(15) -0.0182(17) F6 0.059(2) 0.080(2) 0.090(2) -0.0197(17) -0.0061(15) 0.0082(15) C5 0.049(3) 0.049(2) 0.0339(18) -0.0090(15) -0.0047(16) -0.0159(17) C6 0.083(4) 0.056(2) 0.0316(19) -0.0145(17) -0.0062(19) -0.029(2) C9 0.052(3) 0.048(2) 0.039(2) -0.0088(16) -0.0062(17) -0.0187(18) C8 0.053(3) 0.052(2) 0.047(2) -0.0063(19) 0.0030(19) -0.0099(19) C7 0.085(4) 0.041(2) 0.0345(19) -0.0127(16) 0.008(2) -0.012(2) C3 0.089(4) 0.063(3) 0.067(3) -0.022(2) -0.012(3) -0.031(3) C2 0.106(6) 0.108(5) 0.121(6) -0.048(5) 0.024(4) -0.049(4) C1 0.105(7) 0.101(6) 0.227(12) -0.033(7) -0.091(7) 0.011(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 Si F2 1.540(4) . ? Si F1 1.569(3) . ? Si C3 1.831(5) . ? Si C4 1.868(4) . ? F3 C5 1.340(5) . ? F4 C6 1.339(5) . ? F7 C9 1.347(5) . ? F5 C7 1.336(5) . ? N C1 1.421(8) . ? N C2 1.445(8) . ? N C3 1.488(6) . ? C4 C9 1.380(6) . ? C4 C5 1.388(5) . ? F6 C8 1.342(5) . ? C5 C6 1.372(6) . ? C6 C7 1.372(7) . ? C9 C8 1.367(6) . ? C8 C7 1.375(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C1 H1B 0.9600 . ? C1 H1A 0.9600 . ? C1 H1C 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 F2 Si F1 105.2(2) . . ? F2 Si C3 116.4(3) . . ? F1 Si C3 108.6(2) . . ? F2 Si C4 108.40(18) . . ? F1 Si C4 107.25(18) . . ? C3 Si C4 110.4(2) . . ? C1 N C2 110.6(7) . . ? C1 N C3 112.1(6) . . ? C2 N C3 107.4(5) . . ? C9 C4 C5 115.2(4) . . ? C9 C4 Si 121.3(3) . . ? C5 C4 Si 123.4(3) . . ? F3 C5 C6 117.9(4) . . ? F3 C5 C4 119.4(4) . . ? C6 C5 C4 122.7(4) . . ? F4 C6 C7 120.0(4) . . ? F4 C6 C5 120.2(4) . . ? C7 C6 C5 119.7(4) . . ? F7 C9 C8 117.1(4) . . ? F7 C9 C4 119.3(4) . . ? C8 C9 C4 123.6(4) . . ? F6 C8 C9 121.2(4) . . ? F6 C8 C7 119.5(4) . . ? C9 C8 C7 119.3(4) . . ? F5 C7 C6 120.1(4) . . ? F5 C7 C8 120.4(5) . . ? C6 C7 C8 119.5(4) . . ? N C3 Si 107.0(3) . . ? N C3 H3A 110.3 . . ? Si C3 H3A 110.3 . . ? N C3 H3B 110.3 . . ? Si C3 H3B 110.3 . . ? H3A C3 H3B 108.6 . . ? N C2 H2A 109.5 . . ? N C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N C1 H1B 109.5 . . ? N C1 H1A 109.5 . . ? H1B C1 H1A 109.5 . . ? N C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? H1A C1 H1C 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 F2 Si C4 C9 -153.8(3) . . . . ? F1 Si C4 C9 -40.6(4) . . . . ? C3 Si C4 C9 77.6(4) . . . . ? F2 Si C4 C5 30.4(4) . . . . ? F1 Si C4 C5 143.5(3) . . . . ? C3 Si C4 C5 -98.3(4) . . . . ? C9 C4 C5 F3 -178.6(3) . . . . ? Si C4 C5 F3 -2.6(5) . . . . ? C9 C4 C5 C6 0.1(6) . . . . ? Si C4 C5 C6 176.2(3) . . . . ? F3 C5 C6 F4 -0.7(6) . . . . ? C4 C5 C6 F4 -179.4(4) . . . . ? F3 C5 C6 C7 178.0(4) . . . . ? C4 C5 C6 C7 -0.7(6) . . . . ? C5 C4 C9 F7 180.0(3) . . . . ? Si C4 C9 F7 3.8(5) . . . . ? C5 C4 C9 C8 0.6(6) . . . . ? Si C4 C9 C8 -175.5(3) . . . . ? F7 C9 C8 F6 0.7(6) . . . . ? C4 C9 C8 F6 -179.9(4) . . . . ? F7 C9 C8 C7 179.9(4) . . . . ? C4 C9 C8 C7 -0.7(6) . . . . ? F4 C6 C7 F5 0.1(6) . . . . ? C5 C6 C7 F5 -178.6(4) . . . . ? F4 C6 C7 C8 179.4(4) . . . . ? C5 C6 C7 C8 0.7(6) . . . . ? F6 C8 C7 F5 -1.4(6) . . . . ? C9 C8 C7 F5 179.3(4) . . . . ? F6 C8 C7 C6 179.3(4) . . . . ? C9 C8 C7 C6 0.0(6) . . . . ? C1 N C3 Si 94.1(6) . . . . ? C2 N C3 Si -144.3(4) . . . . ? F2 Si C3 N -68.5(4) . . . . ? F1 Si C3 N 173.0(3) . . . . ? C4 Si C3 N 55.6(4) . . . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 25.66 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 0.736 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.060 ### data_markus26 _database_code_depnum_ccdc_archive 'CCDC 688420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; N-(Pentafluorphenyl-difluor-silyl)-N-(trimetylsilyl)-N'-N'-dimethyl-hydrazine ; _chemical_name_common ;N-(Pentafluorphenyl-difluor-silyl)-N-(trimetylsilyl)-N'-N'- dimethyl-hydrazine ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H15 F7 N2 Si2' _chemical_formula_weight 364.43 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' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 28.767(11) _cell_length_b 8.542(3) _cell_length_c 6.264(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1539.2(10) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.573 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.300 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Omega and Phi scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17049 _diffrn_reflns_av_R_equivalents 0.2516 _diffrn_reflns_av_sigmaI/netI 0.1767 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 30.04 _reflns_number_total 4448 _reflns_number_gt 2893 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STOE IPDS-1' _computing_cell_refinement 'X-AREA (STOE 2003)' _computing_data_reduction 'X-AREA (STOE 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.01' _computing_publication_material 'SHELXTL 5.01' _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^)+(0.0461P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_number_reflns 4448 _refine_ls_number_parameters 224 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1055 _refine_ls_R_factor_gt 0.0851 _refine_ls_wR_factor_ref 0.1563 _refine_ls_wR_factor_gt 0.1507 _refine_ls_goodness_of_fit_ref 0.913 _refine_ls_restrained_S_all 0.913 _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 Si1 Si 0.36643(4) 0.87479(12) 0.99802(16) 0.0205(2) Uani 1 1 d . . . Si2 Si 0.30915(4) 0.59287(13) 0.78217(17) 0.0247(3) Uani 1 1 d . . . F2 F 0.39095(10) 0.8667(3) 1.2223(3) 0.0290(6) Uani 1 1 d . . . F12 F 0.33749(10) 1.0056(3) 0.5795(4) 0.0314(6) Uani 1 1 d . . . F13 F 0.38091(10) 1.2037(3) 0.3111(4) 0.0356(6) Uani 1 1 d . . . F15 F 0.50571(9) 1.2414(3) 0.7881(5) 0.0397(6) Uani 1 1 d . . . F1 F 0.31896(9) 0.9610(3) 1.0482(4) 0.0325(6) Uani 1 1 d . . . C12 C 0.37946(16) 1.0602(5) 0.6331(6) 0.0232(8) Uani 1 1 d . . . F16 F 0.46375(10) 1.0434(3) 1.0546(4) 0.0351(6) Uani 1 1 d . . . C11 C 0.39883(15) 1.0145(5) 0.8271(6) 0.0202(8) Uani 1 1 d . . . F14 F 0.46546(11) 1.3179(3) 0.4121(4) 0.0393(7) Uani 1 1 d . . . N1 N 0.35533(13) 0.7014(4) 0.8896(5) 0.0218(7) Uani 1 1 d . . . C13 C 0.40102(16) 1.1618(5) 0.4938(6) 0.0256(8) Uani 1 1 d . . . N2 N 0.40618(13) 0.6662(4) 0.8808(5) 0.0224(7) Uani 1 1 d . . . C16 C 0.44212(17) 1.0785(5) 0.8705(6) 0.0245(9) Uani 1 1 d . . . C14 C 0.44449(17) 1.2198(5) 0.5465(6) 0.0273(9) Uani 1 1 d . . . C15 C 0.46453(15) 1.1804(5) 0.7362(6) 0.0258(9) Uani 1 1 d . . . C2 C 0.42224(18) 0.6402(6) 0.6644(6) 0.0299(10) Uani 1 1 d . . . H23 H 0.4544(11) 0.628(4) 0.6645(9) 0.053(17) Uiso 1 1 calc R . . H21 H 0.4143(11) 0.726(3) 0.580(3) 0.050(16) Uiso 1 1 calc R . . H22 H 0.4083(10) 0.550(4) 0.610(3) 0.033(13) Uiso 1 1 calc R . . C3 C 0.30951(19) 0.5945(6) 0.4859(7) 0.0404(12) Uani 1 1 d . . . H33 H 0.3201(13) 0.703(4) 0.432(2) 0.042(15) Uiso 1 1 calc R . . H32 H 0.2765(12) 0.571(5) 0.430(2) 0.10(3) Uiso 1 1 calc R . . H31 H 0.3322(13) 0.510(4) 0.431(2) 0.07(2) Uiso 1 1 calc R . . C1 C 0.41904(18) 0.5384(5) 1.0239(7) 0.0316(10) Uani 1 1 d . . . H13 H 0.4538(10) 0.524(2) 1.022(4) 0.043(14) Uiso 1 1 calc R . . H12 H 0.4036(9) 0.439(3) 0.975(3) 0.036(13) Uiso 1 1 calc R . . H11 H 0.4087(10) 0.5640(17) 1.173(4) 0.032(13) Uiso 1 1 calc R . . C5 C 0.25652(19) 0.6929(7) 0.8787(8) 0.0419(12) Uani 1 1 d . . . H53 H 0.2555(7) 0.688(4) 1.037(5) 0.037(14) Uiso 1 1 calc R . . H52 H 0.2286(9) 0.641(3) 0.819(5) 0.063(19) Uiso 1 1 calc R . . H51 H 0.2571(6) 0.804(4) 0.833(5) 0.13(3) Uiso 1 1 calc R . . C4 C 0.3106(2) 0.3873(6) 0.8782(8) 0.0438(14) Uani 1 1 d . . . H43 H 0.3138(14) 0.3863(6) 1.033(6) 0.037(14) Uiso 1 1 calc R . . H42 H 0.3369(12) 0.333(2) 0.814(6) 0.10(3) Uiso 1 1 calc R . . H41 H 0.2819(12) 0.335(2) 0.838(6) 0.11(3) 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 Si1 0.0236(6) 0.0187(5) 0.0193(5) -0.0021(4) 0.0021(5) 0.0003(4) Si2 0.0280(6) 0.0239(5) 0.0220(5) -0.0026(5) 0.0023(5) -0.0043(5) F2 0.0417(17) 0.0252(13) 0.0203(11) -0.0024(9) 0.0002(10) -0.0026(11) F12 0.0245(14) 0.0354(15) 0.0343(13) 0.0026(10) -0.0068(10) -0.0037(11) F13 0.0461(18) 0.0334(14) 0.0272(12) 0.0088(11) -0.0071(12) 0.0028(13) F15 0.0244(14) 0.0441(15) 0.0506(14) -0.0004(14) -0.0007(14) -0.0116(12) F1 0.0286(15) 0.0284(14) 0.0406(14) -0.0070(11) 0.0082(11) 0.0054(11) C12 0.023(2) 0.023(2) 0.0237(18) -0.0028(17) -0.0029(16) 0.0020(17) F16 0.0315(16) 0.0375(15) 0.0363(14) 0.0044(11) -0.0120(11) -0.0063(12) C11 0.024(2) 0.0176(18) 0.0196(18) -0.0017(14) -0.0014(14) 0.0024(16) F14 0.0442(19) 0.0344(16) 0.0394(13) 0.0066(12) 0.0124(12) -0.0066(13) N1 0.0259(19) 0.0200(17) 0.0195(15) -0.0010(14) 0.0022(14) 0.0020(14) C13 0.037(2) 0.0204(19) 0.0197(17) 0.0018(18) 0.0015(19) 0.0032(16) N2 0.024(2) 0.0220(17) 0.0207(15) 0.0027(14) 0.0025(13) 0.0025(14) C16 0.028(2) 0.022(2) 0.0234(19) 0.0020(16) -0.0019(17) 0.0032(17) C14 0.035(3) 0.0180(19) 0.028(2) 0.0004(16) 0.0084(18) -0.0009(17) C15 0.024(2) 0.022(2) 0.031(2) -0.0061(17) 0.0025(17) -0.0031(17) C2 0.030(3) 0.031(2) 0.028(2) -0.0008(19) 0.0067(19) 0.0067(19) C3 0.044(3) 0.049(3) 0.029(2) 0.002(2) -0.003(2) -0.016(2) C1 0.035(3) 0.027(2) 0.032(2) 0.0045(19) 0.003(2) 0.0055(19) C5 0.026(3) 0.047(3) 0.053(3) -0.012(3) 0.003(2) -0.004(2) C4 0.057(4) 0.028(3) 0.047(3) 0.000(2) -0.008(3) -0.012(3) _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 Si1 F2 1.574(2) . ? Si1 F1 1.583(3) . ? Si1 N1 1.660(3) . ? Si1 C11 1.854(4) . ? Si1 N2 2.241(4) . ? Si2 N1 1.754(4) . ? Si2 C5 1.841(6) . ? Si2 C4 1.856(5) . ? Si2 C3 1.856(5) . ? F12 C12 1.337(5) . ? F13 C13 1.331(5) . ? F15 C15 1.335(5) . ? C12 C13 1.378(6) . ? C12 C11 1.393(5) . ? F16 C16 1.344(5) . ? C11 C16 1.387(6) . ? F14 C14 1.332(5) . ? N1 N2 1.494(5) . ? C13 C14 1.385(6) . ? N2 C2 1.449(5) . ? N2 C1 1.461(5) . ? C16 C15 1.372(6) . ? C14 C15 1.363(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 Si1 F1 103.29(15) . . ? F2 Si1 N1 114.32(15) . . ? F1 Si1 N1 109.30(17) . . ? F2 Si1 C11 108.57(17) . . ? F1 Si1 C11 104.43(17) . . ? N1 Si1 C11 115.75(17) . . ? F2 Si1 N2 91.65(14) . . ? F1 Si1 N2 151.07(15) . . ? N1 Si1 N2 41.82(16) . . ? C11 Si1 N2 93.77(16) . . ? N1 Si2 C5 104.6(2) . . ? N1 Si2 C4 111.0(2) . . ? C5 Si2 C4 110.6(3) . . ? N1 Si2 C3 112.1(2) . . ? C5 Si2 C3 109.2(3) . . ? C4 Si2 C3 109.3(2) . . ? F12 C12 C13 117.8(3) . . ? F12 C12 C11 118.9(4) . . ? C13 C12 C11 123.3(4) . . ? C16 C11 C12 114.8(4) . . ? C16 C11 Si1 126.3(3) . . ? C12 C11 Si1 118.9(3) . . ? N2 N1 Si1 90.4(2) . . ? N2 N1 Si2 128.4(2) . . ? Si1 N1 Si2 140.7(2) . . ? F13 C13 C12 121.2(4) . . ? F13 C13 C14 120.1(4) . . ? C12 C13 C14 118.7(4) . . ? C2 N2 C1 112.3(4) . . ? C2 N2 N1 112.2(3) . . ? C1 N2 N1 112.0(3) . . ? C2 N2 Si1 126.3(3) . . ? C1 N2 Si1 121.5(3) . . ? N1 N2 Si1 47.82(16) . . ? F16 C16 C15 116.8(4) . . ? F16 C16 C11 119.7(4) . . ? C15 C16 C11 123.5(4) . . ? F14 C14 C15 121.0(4) . . ? F14 C14 C13 118.9(4) . . ? C15 C14 C13 120.1(4) . . ? F15 C15 C14 119.4(4) . . ? F15 C15 C16 121.0(4) . . ? C14 C15 C16 119.5(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag F12 C12 C11 C16 -179.2(4) . . . . ? C13 C12 C11 C16 -0.4(6) . . . . ? F12 C12 C11 Si1 2.0(5) . . . . ? C13 C12 C11 Si1 -179.2(3) . . . . ? F2 Si1 C11 C16 11.5(4) . . . . ? F1 Si1 C11 C16 121.2(4) . . . . ? N1 Si1 C11 C16 -118.6(4) . . . . ? N2 Si1 C11 C16 -81.5(4) . . . . ? F2 Si1 C11 C12 -169.8(3) . . . . ? F1 Si1 C11 C12 -60.1(3) . . . . ? N1 Si1 C11 C12 60.1(4) . . . . ? N2 Si1 C11 C12 97.2(3) . . . . ? F2 Si1 N1 N2 -62.8(2) . . . . ? F1 Si1 N1 N2 -177.94(18) . . . . ? C11 Si1 N1 N2 64.5(2) . . . . ? F2 Si1 N1 Si2 126.1(3) . . . . ? F1 Si1 N1 Si2 10.9(4) . . . . ? C11 Si1 N1 Si2 -106.6(3) . . . . ? N2 Si1 N1 Si2 -171.1(4) . . . . ? C5 Si2 N1 N2 174.0(3) . . . . ? C4 Si2 N1 N2 54.7(4) . . . . ? C3 Si2 N1 N2 -67.8(4) . . . . ? C5 Si2 N1 Si1 -17.4(4) . . . . ? C4 Si2 N1 Si1 -136.6(3) . . . . ? C3 Si2 N1 Si1 100.8(3) . . . . ? F12 C12 C13 F13 -0.4(6) . . . . ? C11 C12 C13 F13 -179.2(4) . . . . ? F12 C12 C13 C14 179.9(4) . . . . ? C11 C12 C13 C14 1.2(6) . . . . ? Si1 N1 N2 C2 -119.5(3) . . . . ? Si2 N1 N2 C2 53.4(4) . . . . ? Si1 N1 N2 C1 113.2(3) . . . . ? Si2 N1 N2 C1 -74.0(4) . . . . ? Si2 N1 N2 Si1 172.8(3) . . . . ? F2 Si1 N2 C2 -146.0(4) . . . . ? F1 Si1 N2 C2 92.2(5) . . . . ? N1 Si1 N2 C2 88.1(4) . . . . ? C11 Si1 N2 C2 -37.3(4) . . . . ? F2 Si1 N2 C1 33.6(4) . . . . ? F1 Si1 N2 C1 -88.2(4) . . . . ? N1 Si1 N2 C1 -92.2(4) . . . . ? C11 Si1 N2 C1 142.4(4) . . . . ? F2 Si1 N2 N1 125.9(2) . . . . ? F1 Si1 N2 N1 4.0(4) . . . . ? C11 Si1 N2 N1 -125.4(2) . . . . ? C12 C11 C16 F16 179.3(3) . . . . ? Si1 C11 C16 F16 -1.9(6) . . . . ? C12 C11 C16 C15 0.6(6) . . . . ? Si1 C11 C16 C15 179.3(3) . . . . ? F13 C13 C14 F14 0.3(6) . . . . ? C12 C13 C14 F14 179.9(4) . . . . ? F13 C13 C14 C15 178.2(4) . . . . ? C12 C13 C14 C15 -2.2(6) . . . . ? F14 C14 C15 F15 0.2(6) . . . . ? C13 C14 C15 F15 -177.7(4) . . . . ? F14 C14 C15 C16 -179.7(4) . . . . ? C13 C14 C15 C16 2.4(6) . . . . ? F16 C16 C15 F15 -0.3(6) . . . . ? C11 C16 C15 F15 178.4(4) . . . . ? F16 C16 C15 C14 179.6(4) . . . . ? C11 C16 C15 C14 -1.7(7) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.04 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.046 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.104 ### data_woski15 _database_code_depnum_ccdc_archive 'CCDC 688421' _audit_creation_method SHELXL-97 _chemical_name_systematic ; O-[Difluoro(pentafluorphenyl)siyl]-N,N-dimethyl-hydroxylamine ; _chemical_name_common O-(Difluoro(pentafluorphenyl)siyl)-N,N-dimethyl-hydroxylamine _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H6 F7 N O Si' _chemical_formula_weight 293.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.325(1) _cell_length_b 10.809(1) _cell_length_c 15.633(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1068.8(2) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 100 _cell_measurement_theta_min 30.65 _cell_measurement_theta_max 38.29 _exptl_crystal_description Cylinder _exptl_crystal_colour Colourless _exptl_crystal_size_max 1 _exptl_crystal_size_rad 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.822 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.306 _exptl_absorpt_correction_type None _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; Crystal grown in situ by slowly cooling the melt after generation of a suitable seed crystal (m.p. of the sample +10\%C) ; _diffrn_ambient_temperature 143(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 'Nonius CAD4' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 11 _diffrn_reflns_number 3503 _diffrn_reflns_av_R_equivalents 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0760 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 27.15 _reflns_number_total 2320 _reflns_number_gt 1793 _reflns_threshold_expression >2sigma(I) _computing_data_collection CAD4-Software _computing_cell_refinement CAD4-Software _computing_data_reduction CADSHEL _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 5.01' _computing_publication_material 'SHELXTL 5.01' _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^)+(0.0682P)^2^+0.5301P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_number_reflns 2320 _refine_ls_number_parameters 188 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0802 _refine_ls_R_factor_gt 0.0500 _refine_ls_wR_factor_ref 0.1309 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Si Si -0.20417(16) -0.55766(10) -0.13692(7) 0.0270(3) Uani 1 1 d . . . O O -0.3112(5) -0.5452(3) -0.23156(18) 0.0331(6) Uani 1 1 d . . . N N -0.3086(5) -0.4091(3) -0.2143(2) 0.0257(7) Uani 1 1 d . . . F1 F -0.1682(4) -0.7016(2) -0.12687(17) 0.0411(6) Uani 1 1 d . . . C1 C -0.1738(7) -0.3546(5) -0.2797(3) 0.0350(10) Uani 1 1 d . . . H1A H -0.182(9) -0.279(5) -0.273(3) 0.040(14) Uiso 1 1 d . . . H1B H -0.227(7) -0.380(4) -0.339(3) 0.033(12) Uiso 1 1 d . . . H1C H -0.018(9) -0.387(5) -0.269(3) 0.055(16) Uiso 1 1 d . . . F2 F 0.0274(3) -0.5046(2) -0.13091(18) 0.0375(6) Uani 1 1 d . . . C2 C -0.5270(6) -0.3649(4) -0.2209(3) 0.0320(9) Uani 1 1 d . . . H2A H -0.537(7) -0.278(5) -0.211(3) 0.030(11) Uiso 1 1 d . . . H2B H -0.606(7) -0.407(4) -0.179(3) 0.022(11) Uiso 1 1 d . . . H2C H -0.579(8) -0.379(4) -0.281(3) 0.042(14) Uiso 1 1 d . . . C11 C -0.3687(6) -0.5122(3) -0.0437(2) 0.0236(8) Uani 1 1 d . . . F12 F -0.1392(4) -0.3530(2) 0.00128(18) 0.0390(6) Uani 1 1 d . . . C12 C -0.3213(6) -0.4160(3) 0.0115(2) 0.0270(8) Uani 1 1 d . . . F13 F -0.4026(4) -0.2848(2) 0.12775(17) 0.0408(6) Uani 1 1 d . . . C13 C -0.4530(6) -0.3785(4) 0.0762(3) 0.0282(8) Uani 1 1 d . . . F14 F -0.7758(4) -0.4028(2) 0.14891(17) 0.0444(7) Uani 1 1 d . . . C14 C -0.6449(6) -0.4389(4) 0.0867(2) 0.0291(8) Uani 1 1 d . . . F15 F -0.8842(4) -0.5923(2) 0.04494(16) 0.0356(6) Uani 1 1 d . . . C15 C -0.6987(6) -0.5357(3) 0.0344(3) 0.0280(8) Uani 1 1 d . . . F16 F -0.6173(4) -0.6661(2) -0.07956(16) 0.0336(6) Uani 1 1 d . . . C16 C -0.5600(6) -0.5717(4) -0.0290(2) 0.0247(8) Uani 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 Si 0.0186(4) 0.0279(5) 0.0344(6) 0.0002(5) 0.0061(5) 0.0023(4) O 0.0332(15) 0.0317(14) 0.0343(15) -0.0043(12) 0.0039(13) 0.0008(13) N 0.0200(14) 0.0287(16) 0.0283(16) -0.0033(13) 0.0012(13) -0.0010(14) F1 0.0384(13) 0.0335(13) 0.0515(15) 0.0042(12) 0.0141(12) 0.0101(10) C1 0.033(2) 0.042(3) 0.030(2) 0.002(2) 0.0088(18) 0.000(2) F2 0.0142(9) 0.0490(14) 0.0493(15) 0.0093(13) 0.0027(11) 0.0016(10) C2 0.0196(18) 0.035(2) 0.042(3) 0.001(2) -0.0018(18) 0.0076(17) C11 0.0204(17) 0.0242(19) 0.0262(19) 0.0023(15) 0.0006(15) 0.0017(14) F12 0.0267(12) 0.0351(13) 0.0552(15) -0.0012(12) 0.0046(11) -0.0135(10) C12 0.0236(18) 0.0254(18) 0.032(2) 0.0028(16) -0.0016(16) -0.0016(15) F13 0.0467(14) 0.0350(14) 0.0409(14) -0.0095(12) -0.0048(12) -0.0024(11) C13 0.0301(19) 0.024(2) 0.031(2) -0.0002(16) -0.0038(16) 0.0026(16) F14 0.0423(14) 0.0498(16) 0.0411(15) -0.0061(12) 0.0173(12) 0.0050(12) C14 0.0284(19) 0.033(2) 0.0260(19) 0.0024(17) 0.0041(15) 0.0065(16) F15 0.0198(10) 0.0424(15) 0.0446(14) 0.0060(12) 0.0081(10) -0.0041(10) C15 0.0185(16) 0.0294(19) 0.036(2) 0.0088(16) 0.0043(16) -0.0002(15) F16 0.0258(11) 0.0314(13) 0.0436(13) -0.0080(11) 0.0005(10) -0.0029(10) C16 0.0205(17) 0.0229(19) 0.031(2) 0.0013(16) -0.0027(14) 0.0005(14) _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 Si F2 1.576(2) . ? Si F1 1.580(3) . ? Si O 1.633(3) . ? Si C11 1.857(4) . ? Si N 2.117(3) . ? O N 1.495(4) . ? N C1 1.455(5) . ? N C2 1.466(5) . ? C1 H1A 0.83(5) . ? C1 H1B 1.02(5) . ? C1 H1C 1.06(6) . ? C2 H2A 0.96(5) . ? C2 H2B 0.94(4) . ? C2 H2C 1.01(5) . ? C11 C12 1.384(5) . ? C11 C16 1.389(5) . ? F12 C12 1.348(4) . ? C12 C13 1.371(6) . ? F13 C13 1.334(4) . ? C13 C14 1.388(6) . ? F14 C14 1.335(4) . ? C14 C15 1.371(6) . ? F15 C15 1.334(4) . ? C15 C16 1.379(5) . ? F16 C16 1.341(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2 Si F1 102.60(14) . . ? F2 Si O 114.17(16) . . ? F1 Si O 103.37(16) . . ? F2 Si C11 112.20(17) . . ? F1 Si C11 105.26(16) . . ? O Si C11 117.20(17) . . ? F2 Si N 92.77(14) . . ? F1 Si N 148.08(15) . . ? O Si N 44.73(13) . . ? C11 Si N 94.20(15) . . ? N O Si 85.05(19) . . ? C1 N C2 111.8(3) . . ? C1 N O 106.2(3) . . ? C2 N O 107.3(3) . . ? C1 N Si 121.7(3) . . ? C2 N Si 125.6(3) . . ? O N Si 50.22(15) . . ? N C1 H1A 106(4) . . ? N C1 H1B 110(3) . . ? H1A C1 H1B 111(4) . . ? N C1 H1C 108(3) . . ? H1A C1 H1C 112(5) . . ? H1B C1 H1C 111(4) . . ? N C2 H2A 112(3) . . ? N C2 H2B 107(3) . . ? H2A C2 H2B 109(4) . . ? N C2 H2C 109(3) . . ? H2A C2 H2C 106(4) . . ? H2B C2 H2C 114(4) . . ? C12 C11 C16 115.7(3) . . ? C12 C11 Si 124.5(3) . . ? C16 C11 Si 119.7(3) . . ? F12 C12 C13 117.2(3) . . ? F12 C12 C11 119.4(3) . . ? C13 C12 C11 123.4(4) . . ? F13 C13 C12 121.7(4) . . ? F13 C13 C14 119.6(4) . . ? C12 C13 C14 118.7(4) . . ? F14 C14 C15 120.2(4) . . ? F14 C14 C13 119.4(4) . . ? C15 C14 C13 120.3(4) . . ? F15 C15 C14 119.6(3) . . ? F15 C15 C16 121.3(4) . . ? C14 C15 C16 119.1(4) . . ? F16 C16 C15 117.8(3) . . ? F16 C16 C11 119.4(3) . . ? C15 C16 C11 122.8(4) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.15 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.435 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.074