Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Vijeyakumar Kingston' 'Boris Gostevskii' 'Inna Kalikhman ' 'D.Kost' _publ_contact_author_name 'Professor Daniel Kost' _publ_contact_author_email 'kostd@bgumail.bgu.ac.il' data_6a _database_code_CSD 157088 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(N,N-dimethylacethydrazido-N,O)phenylsilicon trifluoromethylsulfonate ; _chemical_name_common 6a _chemical_melting_point '182-184 ĄC' _chemical_formula_moiety ? _chemical_formula_sum 'C15 H23 F3 N4 O5 S Si' _chemical_formula_weight 456.52 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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.4678(15) _cell_length_b 11.032(2) _cell_length_c 11.517(2) _cell_angle_alpha 89.784(5) _cell_angle_beta 84.087(5) _cell_angle_gamma 75.050(5) _cell_volume 1033.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.467 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12650 _diffrn_reflns_av_R_equivalents 0.0241 _diffrn_reflns_av_sigmaI/netI 0.0352 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 28.30 _reflns_number_total 5128 _reflns_number_gt 3913 _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^)+(0.0585P)^2^+0.0032P] 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 5128 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1016 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _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 0.27211(5) 0.79031(4) 0.80126(3) 0.01707(10) Uani 1 1 d . . . C1 C -0.00793(18) 0.85138(15) 0.72330(13) 0.0223(3) Uani 1 1 d . . . C2 C -0.1365(2) 0.94598(16) 0.67011(16) 0.0307(4) Uani 1 1 d . . . H2A H -0.2060 0.9036 0.6316 0.046 Uiso 1 1 calc R . . H2B H -0.0844 0.9931 0.6125 0.046 Uiso 1 1 calc R . . H2C H -0.2040 1.0039 0.7311 0.046 Uiso 1 1 calc R . . C3 C 0.0623(2) 0.63231(17) 0.88988(15) 0.0305(4) Uani 1 1 d . . . H3A H 0.0041 0.7082 0.9358 0.046 Uiso 1 1 calc R . . H3B H 0.1455 0.5799 0.9347 0.046 Uiso 1 1 calc R . . H3C H -0.0162 0.5853 0.8721 0.046 Uiso 1 1 calc R . . C4 C 0.2355(2) 0.55244(15) 0.70998(15) 0.0307(4) Uani 1 1 d . . . H4A H 0.1628 0.4969 0.7046 0.046 Uiso 1 1 calc R . . H4B H 0.3309 0.5093 0.7493 0.046 Uiso 1 1 calc R . . H4C H 0.2726 0.5748 0.6313 0.046 Uiso 1 1 calc R . . C5 C 0.46520(18) 0.74208(14) 0.96194(12) 0.0207(3) Uani 1 1 d . . . C6 C 0.5725(2) 0.65070(15) 1.03283(15) 0.0302(4) Uani 1 1 d . . . H6A H 0.6462 0.6915 1.0685 0.045 Uiso 1 1 calc R . . H6B H 0.6377 0.5801 0.9828 0.045 Uiso 1 1 calc R . . H6C H 0.5047 0.6199 1.0943 0.045 Uiso 1 1 calc R . . C7 C 0.21118(19) 0.99974(14) 0.96983(13) 0.0235(3) Uani 1 1 d . . . H7A H 0.1658 0.9441 1.0223 0.035 Uiso 1 1 calc R . . H7B H 0.1232 1.0525 0.9290 0.035 Uiso 1 1 calc R . . H7C H 0.2595 1.0532 1.0153 0.035 Uiso 1 1 calc R . . C8 C 0.4085(2) 1.00945(15) 0.80507(14) 0.0263(3) Uani 1 1 d . . . H8A H 0.4461 1.0677 0.8528 0.040 Uiso 1 1 calc R . . H8B H 0.3225 1.0570 0.7595 0.040 Uiso 1 1 calc R . . H8C H 0.5011 0.9611 0.7520 0.040 Uiso 1 1 calc R . . C9 C 0.41212(18) 0.77051(14) 0.66489(12) 0.0201(3) Uani 1 1 d . . . C10 C 0.5704(2) 0.68936(15) 0.65783(14) 0.0271(3) Uani 1 1 d . . . H10 H 0.6046 0.6403 0.7231 0.033 Uiso 1 1 calc R . . C11 C 0.6776(2) 0.67975(17) 0.55715(15) 0.0335(4) Uani 1 1 d . . . H11 H 0.7846 0.6245 0.5540 0.040 Uiso 1 1 calc R . . C12 C 0.6298(2) 0.75020(17) 0.46075(15) 0.0326(4) Uani 1 1 d . . . H12 H 0.7037 0.7432 0.3917 0.039 Uiso 1 1 calc R . . C13 C 0.4736(2) 0.83083(17) 0.46569(15) 0.0335(4) Uani 1 1 d . . . H13 H 0.4397 0.8784 0.3995 0.040 Uiso 1 1 calc R . . C14 C 0.3668(2) 0.84213(16) 0.56711(14) 0.0267(3) Uani 1 1 d . . . H14 H 0.2611 0.8994 0.5704 0.032 Uiso 1 1 calc R . . C15 C 0.1113(2) 0.68172(18) 0.35997(15) 0.0347(4) Uani 1 1 d . . . F1 F 0.26517(17) 0.65231(16) 0.38534(12) 0.0700(4) Uani 1 1 d . . . F2 F 0.04177(14) 0.59595(10) 0.40816(9) 0.0424(3) Uani 1 1 d . . . F3 F 0.0332(2) 0.79084(12) 0.41274(11) 0.0652(4) Uani 1 1 d . . . N1 N 0.00946(16) 0.73353(13) 0.71140(11) 0.0254(3) Uani 1 1 d . . . N2 N 0.14439(16) 0.66852(12) 0.77795(11) 0.0221(3) Uani 1 1 d . . . N3 N 0.47308(15) 0.85586(12) 0.95118(11) 0.0229(3) Uani 1 1 d . . . N4 N 0.34126(15) 0.92238(11) 0.88229(10) 0.0186(3) Uani 1 1 d . . . O1 O 0.09281(12) 0.89724(10) 0.78559(9) 0.0221(2) Uani 1 1 d . . . O2 O 0.35615(13) 0.69824(9) 0.90753(9) 0.0209(2) Uani 1 1 d . . . O3 O -0.07466(19) 0.71233(16) 0.19345(13) 0.0552(4) Uani 1 1 d . . . O4 O 0.1735(2) 0.78558(13) 0.16620(13) 0.0584(5) Uani 1 1 d . . . O5 O 0.19316(17) 0.56316(12) 0.16428(11) 0.0401(3) Uani 1 1 d . . . S1 S 0.09933(6) 0.68671(4) 0.20260(3) 0.03063(12) 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 Si1 0.0160(2) 0.0164(2) 0.01915(19) 0.00028(14) -0.00325(14) -0.00422(15) C1 0.0168(7) 0.0265(8) 0.0244(7) 0.0000(6) -0.0048(6) -0.0057(6) C2 0.0240(8) 0.0280(9) 0.0401(9) 0.0009(7) -0.0136(7) -0.0029(7) C3 0.0319(9) 0.0340(9) 0.0316(8) 0.0088(7) -0.0063(7) -0.0183(8) C4 0.0364(10) 0.0191(8) 0.0379(9) -0.0033(7) -0.0095(7) -0.0071(7) C5 0.0190(7) 0.0215(8) 0.0211(7) -0.0019(6) -0.0041(6) -0.0036(6) C6 0.0306(9) 0.0250(8) 0.0342(9) 0.0000(7) -0.0145(7) -0.0013(7) C7 0.0205(7) 0.0214(8) 0.0263(7) -0.0048(6) -0.0015(6) -0.0019(6) C8 0.0312(9) 0.0234(8) 0.0279(8) 0.0014(6) -0.0006(6) -0.0142(7) C9 0.0202(7) 0.0194(7) 0.0211(7) -0.0018(5) -0.0022(6) -0.0057(6) C10 0.0254(8) 0.0246(8) 0.0274(8) 0.0025(6) -0.0010(6) 0.0001(7) C11 0.0253(9) 0.0316(9) 0.0370(9) 0.0020(7) 0.0039(7) 0.0016(7) C12 0.0309(9) 0.0371(10) 0.0274(8) 0.0001(7) 0.0063(7) -0.0080(8) C13 0.0330(10) 0.0402(10) 0.0257(8) 0.0095(7) -0.0020(7) -0.0072(8) C14 0.0215(8) 0.0298(9) 0.0270(8) 0.0048(6) -0.0029(6) -0.0031(7) C15 0.0430(11) 0.0366(10) 0.0283(8) -0.0026(7) 0.0013(7) -0.0192(9) F1 0.0548(9) 0.1153(13) 0.0550(8) -0.0010(8) -0.0203(7) -0.0436(9) F2 0.0518(7) 0.0414(6) 0.0350(6) 0.0115(5) 0.0018(5) -0.0166(5) F3 0.1123(12) 0.0428(7) 0.0389(6) -0.0179(5) 0.0223(7) -0.0288(8) N1 0.0246(7) 0.0257(7) 0.0289(7) 0.0033(5) -0.0117(5) -0.0086(6) N2 0.0228(7) 0.0201(6) 0.0257(6) 0.0016(5) -0.0075(5) -0.0079(5) N3 0.0177(6) 0.0226(7) 0.0281(6) -0.0009(5) -0.0089(5) -0.0025(5) N4 0.0170(6) 0.0175(6) 0.0213(6) 0.0003(5) -0.0031(5) -0.0040(5) O1 0.0171(5) 0.0197(5) 0.0299(6) -0.0026(4) -0.0072(4) -0.0037(4) O2 0.0227(5) 0.0185(5) 0.0232(5) 0.0020(4) -0.0069(4) -0.0069(4) O3 0.0444(9) 0.0668(10) 0.0474(8) 0.0093(7) -0.0144(7) 0.0018(8) O4 0.0953(13) 0.0330(7) 0.0446(8) 0.0001(6) 0.0269(8) -0.0258(8) O5 0.0528(9) 0.0268(7) 0.0362(7) -0.0068(5) 0.0037(6) -0.0051(6) S1 0.0425(3) 0.0228(2) 0.02392(19) 0.00090(15) 0.00315(17) -0.00623(18) _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 O2 1.6833(11) . ? Si1 O1 1.6911(11) . ? Si1 C9 1.8453(15) . ? Si1 N2 1.9645(13) . ? Si1 N4 1.9747(13) . ? C1 N1 1.276(2) . ? C1 O1 1.3600(17) . ? C1 C2 1.482(2) . ? C3 N2 1.503(2) . ? C4 N2 1.490(2) . ? C5 N3 1.279(2) . ? C5 O2 1.3532(17) . ? C5 C6 1.477(2) . ? C7 N4 1.5003(19) . ? C8 N4 1.4862(19) . ? C9 C10 1.401(2) . ? C9 C14 1.402(2) . ? C10 C11 1.383(2) . ? C11 C12 1.387(2) . ? C12 C13 1.386(3) . ? C13 C14 1.387(2) . ? C15 F1 1.322(2) . ? C15 F2 1.329(2) . ? C15 F3 1.330(2) . ? C15 S1 1.8256(18) . ? N1 N2 1.4699(17) . ? N3 N4 1.4729(16) . ? O3 S1 1.4417(16) . ? O4 S1 1.4337(14) . ? O5 S1 1.4343(13) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 Si1 O1 137.05(6) . . ? O2 Si1 C9 112.09(6) . . ? O1 Si1 C9 110.86(6) . . ? O2 Si1 N2 87.54(5) . . ? O1 Si1 N2 83.70(6) . . ? C9 Si1 N2 102.21(6) . . ? O2 Si1 N4 84.15(5) . . ? O1 Si1 N4 88.03(5) . . ? C9 Si1 N4 100.55(6) . . ? N2 Si1 N4 157.24(6) . . ? N1 C1 O1 121.32(13) . . ? N1 C1 C2 122.63(14) . . ? O1 C1 C2 116.05(13) . . ? N3 C5 O2 121.09(13) . . ? N3 C5 C6 123.06(13) . . ? O2 C5 C6 115.85(13) . . ? C10 C9 C14 117.83(14) . . ? C10 C9 Si1 121.26(11) . . ? C14 C9 Si1 120.81(12) . . ? C11 C10 C9 120.90(15) . . ? C10 C11 C12 120.45(16) . . ? C13 C12 C11 119.62(16) . . ? C12 C13 C14 120.07(15) . . ? C13 C14 C9 121.11(15) . . ? F1 C15 F2 106.93(16) . . ? F1 C15 F3 108.33(16) . . ? F2 C15 F3 106.71(15) . . ? F1 C15 S1 111.80(13) . . ? F2 C15 S1 111.05(12) . . ? F3 C15 S1 111.76(13) . . ? C1 N1 N2 107.92(12) . . ? N1 N2 C4 107.17(11) . . ? N1 N2 C3 105.31(12) . . ? C4 N2 C3 109.02(12) . . ? N1 N2 Si1 105.96(9) . . ? C4 N2 Si1 115.44(10) . . ? C3 N2 Si1 113.22(10) . . ? C5 N3 N4 108.60(11) . . ? N3 N4 C8 107.46(11) . . ? N3 N4 C7 105.11(11) . . ? C8 N4 C7 108.04(12) . . ? N3 N4 Si1 105.77(8) . . ? C8 N4 Si1 115.45(9) . . ? C7 N4 Si1 114.27(9) . . ? C1 O1 Si1 112.81(9) . . ? C5 O2 Si1 114.42(9) . . ? O4 S1 O5 114.80(9) . . ? O4 S1 O3 115.37(10) . . ? O5 S1 O3 115.03(10) . . ? O4 S1 C15 103.62(9) . . ? O5 S1 C15 102.28(8) . . ? O3 S1 C15 103.21(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.403 _refine_diff_density_min -0.523 _refine_diff_density_rms 0.063 data_7 _database_code_CSD 157089 _audit_creation_method SHELXL-97 _chemical_name_systematic ; Bis(N,N-dimethylbenzhydrazido-N,O)-bis(trifluoromethylsulfonyl)silicon ; _chemical_name_common 7 _chemical_melting_point '193-5 ĄC ' _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 F6 N4 O8 S2 Si' _chemical_formula_weight 652.63 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' 'S' 'S' 0.1246 0.1234 '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 16.466(5) _cell_length_b 8.193(3) _cell_length_c 20.861(7) _cell_angle_alpha 90.00 _cell_angle_beta 102.427(7) _cell_angle_gamma 90.00 _cell_volume 2748.3(15) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1336 _exptl_absorpt_coefficient_mu 0.330 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.66 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26602 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 23.26 _reflns_number_total 3920 _reflns_number_gt 3163 _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^)+(0.0462P)^2^+6.3094P] 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 3920 _refine_ls_number_parameters 374 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0642 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1258 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.001 _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 0.78009(6) 0.05798(14) 0.03051(5) 0.0226(3) Uani 1 1 d . . . S1 S 0.78500(7) 0.37285(14) 0.11791(5) 0.0358(3) Uani 1 1 d . . . S2 S 0.62425(6) 0.16203(14) -0.06899(5) 0.0323(3) Uani 1 1 d . . . C1 C 0.6784(3) -0.2244(5) 0.0459(2) 0.0326(10) Uani 1 1 d . . . H1A H 0.7248 -0.2891 0.0370 0.049 Uiso 1 1 calc R . . H1B H 0.6393 -0.2002 0.0045 0.049 Uiso 1 1 calc R . . H1C H 0.6497 -0.2863 0.0747 0.049 Uiso 1 1 calc R . . C2 C 0.6406(2) 0.0156(5) 0.0998(2) 0.0319(10) Uani 1 1 d . . . H2A H 0.6183 -0.0557 0.1296 0.048 Uiso 1 1 calc R . . H2B H 0.5968 0.0399 0.0611 0.048 Uiso 1 1 calc R . . H2C H 0.6603 0.1176 0.1224 0.048 Uiso 1 1 calc R . . C3 C 0.8427(2) -0.1125(5) 0.13217(19) 0.0269(9) Uani 1 1 d . . . C4 C 0.9133(2) -0.1620(5) 0.1843(2) 0.0305(10) Uani 1 1 d . . . C5 C 0.9045(3) -0.1734(6) 0.2492(2) 0.0439(12) Uani 1 1 d . . . H5 H 0.8530 -0.1453 0.2598 0.053 Uiso 1 1 calc R . . C6 C 0.9696(3) -0.2249(7) 0.2979(2) 0.0518(14) Uani 1 1 d . . . H6 H 0.9635 -0.2309 0.3421 0.062 Uiso 1 1 calc R . . C7 C 1.0444(3) -0.2681(7) 0.2818(3) 0.0550(14) Uani 1 1 d . . . H7 H 1.0887 -0.3100 0.3146 0.066 Uiso 1 1 calc R . . C8 C 1.0545(3) -0.2501(7) 0.2186(3) 0.0521(13) Uani 1 1 d . . . H8 H 1.1067 -0.2738 0.2083 0.063 Uiso 1 1 calc R . . C9 C 0.9894(3) -0.1982(6) 0.1700(2) 0.0394(11) Uani 1 1 d . . . H9 H 0.9969 -0.1871 0.1263 0.047 Uiso 1 1 calc R . . C10 C 0.8402(4) 0.3470(7) 0.2030(2) 0.0537(14) Uani 1 1 d . . . C11 C 0.8348(3) 0.3187(5) -0.0505(2) 0.0327(10) Uani 1 1 d . . . H11A H 0.8794 0.3581 -0.0710 0.049 Uiso 1 1 calc R . . H11B H 0.8225 0.4016 -0.0201 0.049 Uiso 1 1 calc R . . H11C H 0.7849 0.2974 -0.0845 0.049 Uiso 1 1 calc R . . C12 C 0.9453(2) 0.1966(5) 0.02956(19) 0.0299(10) Uani 1 1 d . . . H12A H 0.9678 0.0951 0.0512 0.045 Uiso 1 1 calc R . . H12B H 0.9397 0.2778 0.0628 0.045 Uiso 1 1 calc R . . H12C H 0.9831 0.2381 0.0029 0.045 Uiso 1 1 calc R . . C13 C 0.8203(2) -0.0626(5) -0.07264(18) 0.0254(9) Uani 1 1 d . . . C14 C 0.8161(2) -0.1878(5) -0.12395(18) 0.0278(9) Uani 1 1 d . . . C15 C 0.8700(3) -0.1811(6) -0.16741(19) 0.0364(11) Uani 1 1 d . . . H15 H 0.9116 -0.0989 -0.1626 0.044 Uiso 1 1 calc R . . C16 C 0.8625(3) -0.2941(6) -0.2172(2) 0.0444(12) Uani 1 1 d . . . H16 H 0.8997 -0.2913 -0.2463 0.053 Uiso 1 1 calc R . . C17 C 0.8011(3) -0.4114(6) -0.2248(2) 0.0456(13) Uani 1 1 d . . . H17 H 0.7952 -0.4871 -0.2600 0.055 Uiso 1 1 calc R . . C18 C 0.7479(3) -0.4199(6) -0.1819(2) 0.0422(11) Uani 1 1 d . . . H18 H 0.7063 -0.5020 -0.1870 0.051 Uiso 1 1 calc R . . C19 C 0.7560(3) -0.3081(5) -0.1315(2) 0.0359(10) Uani 1 1 d . . . H19 H 0.7199 -0.3139 -0.1017 0.043 Uiso 1 1 calc R . . C20 C 0.5655(3) 0.3459(6) -0.0578(3) 0.0486(13) Uani 1 1 d . . . F1 F 0.9191(2) 0.3179(5) 0.20568(16) 0.0900(12) Uani 1 1 d . . . F2 F 0.8323(3) 0.4803(4) 0.23588(15) 0.0941(13) Uani 1 1 d . . . F3 F 0.8096(2) 0.2248(4) 0.23100(14) 0.0677(9) Uani 1 1 d . . . F4 F 0.61188(18) 0.4766(4) -0.05582(18) 0.0726(10) Uani 1 1 d . . . F5 F 0.53729(18) 0.3358(4) -0.00349(17) 0.0663(9) Uani 1 1 d . . . F6 F 0.50133(17) 0.3572(4) -0.10811(17) 0.0740(10) Uani 1 1 d . . . N1 N 0.71098(19) -0.0677(4) 0.07893(15) 0.0270(8) Uani 1 1 d . . . N2 N 0.7677(2) -0.1197(4) 0.14034(15) 0.0304(8) Uani 1 1 d . . . N3 N 0.86205(19) 0.1641(4) -0.01356(14) 0.0246(7) Uani 1 1 d . . . N4 N 0.8767(2) 0.0491(4) -0.06374(15) 0.0277(8) Uani 1 1 d . . . O1 O 0.85972(15) -0.0593(3) 0.07562(12) 0.0264(6) Uani 1 1 d . . . O2 O 0.79963(16) 0.2087(3) 0.09449(12) 0.0297(7) Uani 1 1 d . . . O3 O 0.8293(2) 0.4938(4) 0.09050(16) 0.0491(9) Uani 1 1 d . . . O4 O 0.7003(2) 0.4003(4) 0.11996(18) 0.0525(9) Uani 1 1 d . . . O5 O 0.69346(15) 0.1819(3) -0.00793(12) 0.0262(6) Uani 1 1 d . . . O6 O 0.6528(2) 0.1855(5) -0.12779(14) 0.0520(9) Uani 1 1 d . . . O7 O 0.57137(17) 0.0282(4) -0.06437(14) 0.0399(8) Uani 1 1 d . . . O8 O 0.76234(15) -0.0694(3) -0.03688(12) 0.0266(6) 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 Si1 0.0203(6) 0.0284(6) 0.0195(5) 0.0014(5) 0.0051(4) 0.0017(5) S1 0.0399(7) 0.0345(6) 0.0345(6) -0.0015(5) 0.0116(5) -0.0003(5) S2 0.0255(6) 0.0421(7) 0.0272(5) 0.0044(5) 0.0012(4) 0.0027(5) C1 0.029(2) 0.031(2) 0.037(2) 0.0042(19) 0.0067(19) -0.0046(19) C2 0.022(2) 0.042(3) 0.033(2) 0.003(2) 0.0101(18) 0.0011(19) C3 0.026(2) 0.030(2) 0.026(2) 0.0054(18) 0.0076(17) 0.0000(18) C4 0.028(2) 0.031(2) 0.030(2) 0.0078(19) 0.0007(18) -0.0067(19) C5 0.036(3) 0.061(3) 0.036(3) 0.010(2) 0.009(2) -0.011(2) C6 0.049(3) 0.072(4) 0.031(3) 0.014(2) 0.000(2) -0.021(3) C7 0.041(3) 0.065(4) 0.051(3) 0.026(3) -0.009(2) -0.008(3) C8 0.032(3) 0.063(3) 0.058(3) 0.014(3) 0.003(2) 0.010(3) C9 0.032(3) 0.045(3) 0.039(3) 0.006(2) 0.004(2) 0.006(2) C10 0.073(4) 0.054(3) 0.038(3) -0.007(3) 0.020(3) -0.013(3) C11 0.036(2) 0.030(2) 0.034(2) 0.0116(19) 0.0108(19) 0.0015(19) C12 0.024(2) 0.037(2) 0.029(2) -0.0017(19) 0.0064(17) -0.0054(19) C13 0.026(2) 0.031(2) 0.0189(19) 0.0060(18) 0.0039(16) 0.0068(19) C14 0.028(2) 0.035(2) 0.019(2) 0.0020(18) 0.0014(16) 0.0083(19) C15 0.033(2) 0.052(3) 0.024(2) -0.007(2) 0.0054(18) 0.003(2) C16 0.044(3) 0.062(3) 0.027(2) -0.006(2) 0.010(2) 0.013(3) C17 0.053(3) 0.049(3) 0.030(2) -0.012(2) -0.001(2) 0.014(3) C18 0.049(3) 0.033(3) 0.041(3) -0.007(2) 0.000(2) 0.005(2) C19 0.038(3) 0.038(3) 0.030(2) 0.002(2) 0.0039(19) 0.004(2) C20 0.030(3) 0.046(3) 0.065(3) 0.016(3) -0.002(2) 0.001(2) F1 0.058(2) 0.142(4) 0.059(2) -0.005(2) -0.0126(17) -0.011(2) F2 0.174(4) 0.062(2) 0.0475(19) -0.0295(17) 0.028(2) -0.029(2) F3 0.106(3) 0.061(2) 0.0385(16) 0.0005(15) 0.0196(17) -0.0070(19) F4 0.0509(18) 0.0388(17) 0.123(3) 0.0177(18) 0.0075(18) 0.0042(15) F5 0.0548(19) 0.062(2) 0.090(2) 0.0010(18) 0.0317(17) 0.0218(16) F6 0.0380(17) 0.072(2) 0.098(2) 0.0314(19) -0.0151(16) 0.0131(15) N1 0.0198(17) 0.035(2) 0.0265(18) 0.0058(15) 0.0046(14) 0.0021(15) N2 0.030(2) 0.036(2) 0.0247(18) 0.0044(15) 0.0047(15) -0.0005(16) N3 0.0256(17) 0.0283(19) 0.0205(16) 0.0002(14) 0.0060(13) 0.0015(15) N4 0.0279(19) 0.034(2) 0.0217(17) -0.0014(15) 0.0071(14) 0.0013(17) O1 0.0221(14) 0.0315(16) 0.0267(14) 0.0060(12) 0.0080(11) 0.0043(12) O2 0.0241(15) 0.0426(18) 0.0219(14) -0.0001(13) 0.0034(11) -0.0032(13) O3 0.063(2) 0.0364(18) 0.055(2) -0.0012(16) 0.0266(17) -0.0043(16) O4 0.044(2) 0.048(2) 0.070(2) -0.0026(18) 0.0215(17) 0.0092(16) O5 0.0239(14) 0.0319(15) 0.0214(13) -0.0007(12) 0.0023(11) 0.0051(12) O6 0.0435(19) 0.086(3) 0.0244(16) 0.0036(17) 0.0023(14) -0.0055(18) O7 0.0305(16) 0.0430(19) 0.0415(17) 0.0027(14) -0.0025(13) -0.0002(14) O8 0.0253(14) 0.0302(15) 0.0256(14) -0.0034(12) 0.0083(11) -0.0021(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 Si1 O8 1.724(3) . ? Si1 O1 1.731(3) . ? Si1 O5 1.793(3) . ? Si1 O2 1.796(3) . ? Si1 N1 1.967(3) . ? Si1 N3 1.989(3) . ? S1 O3 1.421(3) . ? S1 O4 1.422(3) . ? S1 O2 1.469(3) . ? S1 C10 1.823(5) . ? S2 O7 1.416(3) . ? S2 O6 1.418(3) . ? S2 O5 1.524(3) . ? S2 C20 1.833(5) . ? C1 N1 1.501(5) . ? C2 N1 1.488(5) . ? C3 N2 1.284(5) . ? C3 O1 1.343(5) . ? C3 C4 1.467(6) . ? C4 C9 1.383(6) . ? C4 C5 1.395(6) . ? C5 C6 1.375(7) . ? C6 C7 1.392(7) . ? C7 C8 1.372(7) . ? C8 C9 1.374(6) . ? C10 F1 1.310(6) . ? C10 F2 1.312(6) . ? C10 F3 1.313(6) . ? C11 N3 1.500(5) . ? C12 N3 1.493(5) . ? C13 N4 1.289(5) . ? C13 O8 1.332(4) . ? C13 C14 1.473(6) . ? C14 C19 1.381(6) . ? C14 C15 1.399(6) . ? C15 C16 1.378(6) . ? C16 C17 1.380(7) . ? C17 C18 1.382(7) . ? C18 C19 1.379(6) . ? C20 F4 1.311(6) . ? C20 F5 1.316(6) . ? C20 F6 1.322(6) . ? N1 N2 1.477(4) . ? N3 N4 1.467(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 O8 Si1 O1 94.76(14) . . ? O8 Si1 O5 89.95(13) . . ? O1 Si1 O5 173.60(13) . . ? O8 Si1 O2 173.62(14) . . ? O1 Si1 O2 89.09(13) . . ? O5 Si1 O2 86.62(13) . . ? O8 Si1 N1 94.98(14) . . ? O1 Si1 N1 83.37(13) . . ? O5 Si1 N1 91.91(13) . . ? O2 Si1 N1 90.51(14) . . ? O8 Si1 N3 84.29(13) . . ? O1 Si1 N3 89.08(13) . . ? O5 Si1 N3 95.71(13) . . ? O2 Si1 N3 90.70(13) . . ? N1 Si1 N3 172.34(14) . . ? O3 S1 O4 119.5(2) . . ? O3 S1 O2 111.71(18) . . ? O4 S1 O2 112.78(19) . . ? O3 S1 C10 106.3(2) . . ? O4 S1 C10 106.0(2) . . ? O2 S1 C10 97.7(2) . . ? O7 S2 O6 119.2(2) . . ? O7 S2 O5 112.70(17) . . ? O6 S2 O5 112.38(17) . . ? O7 S2 C20 106.2(2) . . ? O6 S2 C20 106.3(2) . . ? O5 S2 C20 97.25(19) . . ? N2 C3 O1 121.4(3) . . ? N2 C3 C4 121.3(3) . . ? O1 C3 C4 117.3(3) . . ? C9 C4 C5 118.9(4) . . ? C9 C4 C3 120.6(4) . . ? C5 C4 C3 120.5(4) . . ? C6 C5 C4 120.8(5) . . ? C5 C6 C7 119.2(4) . . ? C8 C7 C6 120.1(4) . . ? C7 C8 C9 120.4(5) . . ? C8 C9 C4 120.4(4) . . ? F1 C10 F2 109.8(5) . . ? F1 C10 F3 108.3(5) . . ? F2 C10 F3 108.1(4) . . ? F1 C10 S1 110.2(3) . . ? F2 C10 S1 109.1(4) . . ? F3 C10 S1 111.3(4) . . ? N4 C13 O8 122.0(4) . . ? N4 C13 C14 121.2(3) . . ? O8 C13 C14 116.8(3) . . ? C19 C14 C15 119.5(4) . . ? C19 C14 C13 120.0(4) . . ? C15 C14 C13 120.4(4) . . ? C16 C15 C14 119.8(4) . . ? C15 C16 C17 119.9(4) . . ? C16 C17 C18 120.8(4) . . ? C19 C18 C17 119.3(5) . . ? C18 C19 C14 120.7(4) . . ? F4 C20 F5 109.6(5) . . ? F4 C20 F6 109.2(4) . . ? F5 C20 F6 108.6(4) . . ? F4 C20 S2 110.8(3) . . ? F5 C20 S2 110.6(3) . . ? F6 C20 S2 108.1(4) . . ? N2 N1 C2 105.4(3) . . ? N2 N1 C1 104.3(3) . . ? C2 N1 C1 107.6(3) . . ? N2 N1 Si1 105.6(2) . . ? C2 N1 Si1 118.9(3) . . ? C1 N1 Si1 113.7(2) . . ? C3 N2 N1 108.5(3) . . ? N4 N3 C12 105.9(3) . . ? N4 N3 C11 104.6(3) . . ? C12 N3 C11 107.0(3) . . ? N4 N3 Si1 106.4(2) . . ? C12 N3 Si1 115.2(2) . . ? C11 N3 Si1 116.7(2) . . ? C13 N4 N3 109.5(3) . . ? C3 O1 Si1 112.4(2) . . ? S1 O2 Si1 149.43(19) . . ? S2 O5 Si1 133.85(17) . . ? C13 O8 Si1 114.5(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 23.26 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.372 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.065