# Copyright The Royal Society of Chemistry, 1998 # Contact person J.D. Woollins # E-mail J.D.Woollins@lboro.ac.uk # Authors' names P.Kilian, J.Marek, R.Marek, J.Touzin, O.Humpa, J.Novosad and #J.D.Woollins # Journal J. Chem. Soc., Dalton Trans. data_3 _audit_creation_method SHELXL _chemical_name_systematic ; 2,4-(naphthalene-1,8-diyl)-3-trimethyl silyl-1,3,2,4-thiazadiphosphetidine-2,4- disulfide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H15 N P2 S3 Si' _chemical_formula_weight 371.47 _chemical_melting_point '440-442 K' _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' .0817 .0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9437(15) _cell_length_b 11.490(2) _cell_length_c 17.165(4) _cell_angle_alpha 76.08(2) _cell_angle_beta 89.74(2) _cell_angle_gamma 87.545(15) _cell_volume 1710.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150.0(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 1.00 _exptl_crystal_size_mid 1.00 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.442 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.679 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5499 _exptl_absorpt_correction_T_max 0.9050 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150.0(1) _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6226 _diffrn_reflns_av_R_equivalents 0.0443 _diffrn_reflns_av_sigmaI/netI 0.0342 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.22 _diffrn_reflns_theta_max 25.05 _reflns_number_total 6008 _reflns_number_gt 5112 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0939P)^2^+2.4000P] 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 6008 _refine_ls_number_parameters 481 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1138 _refine_ls_goodness_of_fit_ref 0.884 _refine_ls_restrained_S_all 0.884 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.11997(8) -0.83312(7) 0.76281(5) 0.02932(19) Uani 1 d . . . S3 S -0.21789(8) -0.94656(6) 0.71607(4) 0.02430(17) Uani 1 d . . . S2 S -0.51313(9) -0.73345(8) 0.66784(6) 0.0373(2) Uani 1 d . . . S101 S 0.03123(8) -1.16974(7) 0.81106(5) 0.02823(18) Uani 1 d . . . S103 S 0.38520(8) -1.04661(6) 0.76946(4) 0.02249(17) Uani 1 d . . . S102 S 0.67415(8) -1.25619(7) 0.76030(5) 0.02732(18) Uani 1 d . . . Si Si -0.12712(10) -0.55749(7) 0.66195(5) 0.0295(2) Uani 1 d . . . Si10 Si 0.33094(9) -1.43988(7) 0.85975(5) 0.02438(19) Uani 1 d . . . P1 P -0.04068(8) -0.82774(6) 0.68915(4) 0.02064(17) Uani 1 d . . . P2 P -0.31267(8) -0.78115(7) 0.64763(4) 0.02350(18) Uani 1 d . . . P101 P 0.23631(8) -1.16724(6) 0.84064(4) 0.01984(17) Uani 1 d . . . P102 P 0.51322(7) -1.20592(6) 0.81931(4) 0.01852(17) Uani 1 d . . . N N -0.1662(3) -0.7113(2) 0.67364(14) 0.0227(5) Uani 1 d . . . N100 N 0.3543(2) -1.2818(2) 0.83284(13) 0.0202(5) Uani 1 d . . . C1 C 0.0058(3) -0.8378(2) 0.58890(17) 0.0230(6) Uani 1 d . . . C2 C 0.1485(4) -0.8647(3) 0.5685(2) 0.0310(7) Uani 1 d . . . C3 C 0.1814(4) -0.8734(3) 0.4892(2) 0.0397(8) Uani 1 d . . . C4 C 0.0718(5) -0.8551(3) 0.4332(2) 0.0406(9) Uani 1 d . . . C5 C -0.0771(4) -0.8268(3) 0.45160(18) 0.0341(7) Uani 1 d . . . C10 C -0.1132(3) -0.8173(3) 0.53043(17) 0.0255(6) Uani 1 d . . . C9 C -0.2655(4) -0.7902(3) 0.54737(18) 0.0278(6) Uani 1 d . . . C8 C -0.3734(4) -0.7736(3) 0.4889(2) 0.0382(8) Uani 1 d . . . C7 C -0.3356(5) -0.7832(4) 0.4110(2) 0.0494(10) Uani 1 d . . . C6 C -0.1927(5) -0.8090(3) 0.3932(2) 0.0443(9) Uani 1 d . . . C11 C -0.1148(5) -0.5363(4) 0.7650(3) 0.0510(10) Uani 1 d . . . C12 C -0.2810(5) -0.4661(4) 0.6034(3) 0.0479(10) Uani 1 d . . . C13 C 0.0534(4) -0.5342(3) 0.6080(2) 0.0371(8) Uani 1 d . . . C101 C 0.2760(3) -1.1496(2) 0.93945(16) 0.0204(5) Uani 1 d . . . C102 C 0.1637(3) -1.1252(3) 0.98849(18) 0.0264(6) Uani 1 d . . . C103 C 0.1950(4) -1.1143(3) 1.0663(2) 0.0354(7) Uani 1 d . . . C104 C 0.3387(4) -1.1275(3) 1.09421(19) 0.0329(7) Uani 1 d . . . C105 C 0.4573(3) -1.1515(3) 1.04527(17) 0.0264(6) Uani 1 d . . . C110 C 0.4279(3) -1.1639(2) 0.96669(16) 0.0210(6) Uani 1 d . . . C109 C 0.5513(3) -1.1894(2) 0.91872(16) 0.0204(5) Uani 1 d . . . C108 C 0.6945(3) -1.2020(3) 0.94970(18) 0.0261(6) Uani 1 d . . . C107 C 0.7211(4) -1.1889(3) 1.02778(19) 0.0312(7) Uani 1 d . . . C106 C 0.6066(4) -1.1641(3) 1.07386(18) 0.0309(7) Uani 1 d . . . C111 C 0.2844(6) -1.4848(4) 0.7673(3) 0.0492(10) Uani 1 d . . . C112 C 0.5118(4) -1.5121(3) 0.8991(3) 0.0412(8) Uani 1 d . . . C113 C 0.1806(4) -1.4681(3) 0.9353(2) 0.0413(8) Uani 1 d . . . H2 H 0.224(4) -0.878(3) 0.6046(19) 0.019(8) Uiso 1 d . . . H3 H 0.276(5) -0.893(4) 0.478(2) 0.044(11) Uiso 1 d . . . H4 H 0.096(5) -0.857(4) 0.382(3) 0.052(12) Uiso 1 d . . . H8 H -0.478(4) -0.753(3) 0.497(2) 0.040(10) Uiso 1 d . . . H7 H -0.412(5) -0.772(4) 0.373(3) 0.057(13) Uiso 1 d . . . H6 H -0.157(5) -0.811(4) 0.341(3) 0.072(15) Uiso 1 d . . . H102 H 0.070(4) -1.116(3) 0.969(2) 0.030(9) Uiso 1 d . . . H103 H 0.124(5) -1.102(4) 1.096(3) 0.049(12) Uiso 1 d . . . H104 H 0.364(5) -1.119(4) 1.149(3) 0.066(14) Uiso 1 d . . . H108 H 0.774(4) -1.218(3) 0.917(2) 0.035(9) Uiso 1 d . . . H107 H 0.815(4) -1.203(3) 1.049(2) 0.038(10) Uiso 1 d . . . H106 H 0.623(5) -1.158(4) 1.129(3) 0.054(12) Uiso 1 d . . . H11A H -0.200(6) -0.562(5) 0.786(3) 0.076(17) Uiso 1 d . . . H11B H -0.108(5) -0.453(5) 0.760(3) 0.072(15) Uiso 1 d . . . H11C H -0.031(6) -0.595(5) 0.792(3) 0.088(18) Uiso 1 d . . . H11D H 0.197(6) -1.440(4) 0.741(3) 0.068(15) Uiso 1 d . . . H11E H 0.366(6) -1.461(5) 0.729(3) 0.089(18) Uiso 1 d . . . H11F H 0.267(5) -1.569(4) 0.782(3) 0.058(13) Uiso 1 d . . . H12A H -0.371(6) -0.484(5) 0.626(3) 0.073(16) Uiso 1 d . . . H12B H -0.258(6) -0.381(5) 0.593(3) 0.087(17) Uiso 1 d . . . H12C H -0.286(4) -0.487(3) 0.557(2) 0.029(9) Uiso 1 d . . . H12D H 0.559(5) -1.465(4) 0.927(3) 0.060(14) Uiso 1 d . . . H12E H 0.497(5) -1.593(4) 0.929(3) 0.052(12) Uiso 1 d . . . H12F H 0.570(6) -1.520(5) 0.859(3) 0.074(16) Uiso 1 d . . . H13A H 0.071(5) -0.456(4) 0.594(3) 0.056(12) Uiso 1 d . . . H13B H 0.057(5) -0.570(4) 0.560(3) 0.068(14) Uiso 1 d . . . H13C H 0.137(4) -0.585(3) 0.641(2) 0.033(9) Uiso 1 d . . . H13D H 0.204(5) -1.430(4) 0.984(3) 0.073(15) Uiso 1 d . . . H13E H 0.085(5) -1.435(4) 0.911(3) 0.057(12) Uiso 1 d . . . H13F H 0.176(5) -1.548(4) 0.953(3) 0.057(12) Uiso 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 S1 0.0270(4) 0.0317(4) 0.0301(4) -0.0096(3) -0.0080(3) 0.0020(3) S3 0.0282(4) 0.0231(4) 0.0208(4) -0.0033(3) 0.0020(3) -0.0035(3) S2 0.0220(4) 0.0410(5) 0.0476(5) -0.0084(4) 0.0011(3) 0.0006(3) S101 0.0196(3) 0.0354(4) 0.0290(4) -0.0062(3) -0.0025(3) -0.0008(3) S103 0.0246(4) 0.0212(3) 0.0199(3) -0.0015(3) 0.0007(3) -0.0010(3) S102 0.0239(4) 0.0299(4) 0.0307(4) -0.0123(3) 0.0077(3) -0.0019(3) Si 0.0304(4) 0.0219(4) 0.0379(5) -0.0107(4) -0.0041(4) 0.0007(3) Si10 0.0254(4) 0.0202(4) 0.0272(4) -0.0044(3) 0.0002(3) -0.0044(3) P1 0.0220(4) 0.0204(4) 0.0201(4) -0.0062(3) -0.0004(3) 0.0000(3) P2 0.0222(4) 0.0247(4) 0.0233(4) -0.0049(3) -0.0010(3) -0.0022(3) P101 0.0195(3) 0.0212(4) 0.0188(4) -0.0049(3) 0.0003(3) -0.0007(3) P102 0.0188(3) 0.0194(3) 0.0180(3) -0.0055(3) 0.0014(3) -0.0024(3) N 0.0215(12) 0.0219(12) 0.0262(12) -0.0088(10) -0.0006(9) -0.0004(9) N100 0.0191(11) 0.0247(12) 0.0176(11) -0.0065(9) 0.0005(9) -0.0028(9) C1 0.0311(15) 0.0188(13) 0.0198(14) -0.0052(11) 0.0064(11) -0.0052(11) C2 0.0336(17) 0.0242(15) 0.0373(18) -0.0110(13) 0.0073(15) -0.0040(13) C3 0.047(2) 0.0306(17) 0.044(2) -0.0145(15) 0.0227(17) -0.0069(15) C4 0.065(2) 0.0313(17) 0.0278(17) -0.0104(14) 0.0194(17) -0.0148(16) C5 0.056(2) 0.0274(16) 0.0206(15) -0.0064(12) 0.0077(14) -0.0138(14) C10 0.0372(16) 0.0209(14) 0.0182(14) -0.0034(11) 0.0026(12) -0.0092(12) C9 0.0342(16) 0.0265(15) 0.0220(15) -0.0038(12) -0.0044(12) -0.0059(12) C8 0.043(2) 0.0406(19) 0.0292(17) -0.0044(14) -0.0100(15) -0.0078(16) C7 0.068(3) 0.053(2) 0.0257(18) -0.0055(16) -0.0166(18) -0.010(2) C6 0.075(3) 0.041(2) 0.0178(16) -0.0060(14) -0.0031(16) -0.0146(18) C11 0.054(3) 0.053(3) 0.059(3) -0.041(2) 0.003(2) 0.003(2) C12 0.046(2) 0.0274(19) 0.067(3) -0.0065(18) -0.014(2) 0.0061(16) C13 0.0410(19) 0.0289(17) 0.0394(19) -0.0028(15) -0.0039(15) -0.0104(15) C101 0.0260(14) 0.0194(13) 0.0164(13) -0.0054(10) 0.0021(11) -0.0025(11) C102 0.0267(16) 0.0277(15) 0.0258(15) -0.0086(12) 0.0047(12) 0.0009(12) C103 0.0443(19) 0.0359(18) 0.0272(17) -0.0106(14) 0.0131(15) -0.0005(14) C104 0.0464(19) 0.0319(17) 0.0226(15) -0.0107(13) 0.0042(14) -0.0025(14) C105 0.0381(17) 0.0218(14) 0.0196(14) -0.0052(11) -0.0004(12) -0.0031(12) C110 0.0274(14) 0.0166(13) 0.0192(13) -0.0041(10) 0.0010(11) -0.0028(11) C109 0.0251(14) 0.0181(13) 0.0173(13) -0.0025(10) -0.0013(10) -0.0036(10) C108 0.0256(15) 0.0255(15) 0.0263(15) -0.0042(12) -0.0019(12) -0.0029(12) C107 0.0292(16) 0.0339(17) 0.0309(17) -0.0071(13) -0.0096(13) -0.0069(13) C106 0.0429(18) 0.0296(16) 0.0213(15) -0.0074(12) -0.0077(13) -0.0048(13) C111 0.068(3) 0.039(2) 0.047(2) -0.0208(18) -0.008(2) -0.016(2) C112 0.0345(19) 0.0306(19) 0.051(2) 0.0040(17) 0.0033(17) 0.0023(15) C113 0.0344(19) 0.0324(19) 0.048(2) 0.0073(16) 0.0087(16) -0.0029(15) _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 S1 P1 1.9075(11) . ? S3 P1 2.1129(11) . ? S3 P2 2.1231(12) . ? S2 P2 1.9070(11) . ? S101 P101 1.9086(10) . ? S103 P102 2.1142(11) . ? S103 P101 2.1251(11) . ? S102 P102 1.9048(10) . ? Si N 1.780(2) . ? Si C12 1.840(4) . ? Si C11 1.848(4) . ? Si C13 1.855(4) . ? Si10 N100 1.785(2) . ? Si10 C111 1.838(4) . ? Si10 C112 1.841(4) . ? Si10 C113 1.848(4) . ? P1 N 1.680(2) . ? P1 C1 1.798(3) . ? P1 P2 2.5362(11) . ? P2 N 1.682(2) . ? P2 C9 1.796(3) . ? P101 N100 1.681(2) . ? P101 C101 1.794(3) . ? P101 P102 2.5379(10) . ? P102 N100 1.685(2) . ? P102 C109 1.797(3) . ? C1 C2 1.364(4) . ? C1 C10 1.438(4) . ? C2 C3 1.418(5) . ? C3 C4 1.350(6) . ? C4 C5 1.410(5) . ? C5 C6 1.418(5) . ? C5 C10 1.418(4) . ? C10 C9 1.429(4) . ? C9 C8 1.369(4) . ? C8 C7 1.406(5) . ? C7 C6 1.350(6) . ? C101 C102 1.371(4) . ? C101 C110 1.429(4) . ? C102 C103 1.402(5) . ? C103 C104 1.364(5) . ? C104 C105 1.409(4) . ? C105 C106 1.414(5) . ? C105 C110 1.417(4) . ? C110 C109 1.436(4) . ? C109 C108 1.378(4) . ? C108 C107 1.407(4) . ? C107 C106 1.354(5) . ? 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 P1 S3 P2 73.56(4) . . ? P102 S103 P101 73.55(4) . . ? N Si C12 107.96(16) . . ? N Si C11 105.31(18) . . ? C12 Si C11 112.6(2) . . ? N Si C13 106.54(14) . . ? C12 Si C13 111.6(2) . . ? C11 Si C13 112.4(2) . . ? N100 Si10 C111 107.13(16) . . ? N100 Si10 C112 107.36(15) . . ? C111 Si10 C112 109.3(2) . . ? N100 Si10 C113 107.10(15) . . ? C111 Si10 C113 113.0(2) . . ? C112 Si10 C113 112.64(18) . . ? N P1 C1 102.84(13) . . ? N P1 S1 118.79(9) . . ? C1 P1 S1 117.78(11) . . ? N P1 S3 89.36(9) . . ? C1 P1 S3 101.35(10) . . ? S1 P1 S3 121.68(5) . . ? N P1 P2 41.05(8) . . ? C1 P1 P2 90.11(10) . . ? S1 P1 P2 151.09(4) . . ? S3 P1 P2 53.40(3) . . ? N P2 C9 102.30(13) . . ? N P2 S2 121.20(9) . . ? C9 P2 S2 118.09(11) . . ? N P2 S3 88.97(9) . . ? C9 P2 S3 101.35(11) . . ? S2 P2 S3 119.60(5) . . ? N P2 P1 41.00(8) . . ? C9 P2 P1 89.74(11) . . ? S2 P2 P1 151.79(5) . . ? S3 P2 P1 53.04(3) . . ? N100 P101 C101 102.74(12) . . ? N100 P101 S101 119.23(9) . . ? C101 P101 S101 117.57(10) . . ? N100 P101 S103 88.91(9) . . ? C101 P101 S103 101.69(9) . . ? S101 P101 S103 121.61(5) . . ? N100 P101 P102 41.13(8) . . ? C101 P101 P102 89.98(10) . . ? S101 P101 P102 151.52(4) . . ? S103 P101 P102 53.03(3) . . ? N100 P102 C109 102.11(12) . . ? N100 P102 S102 120.08(9) . . ? C109 P102 S102 118.22(10) . . ? N100 P102 S103 89.18(9) . . ? C109 P102 S103 101.88(9) . . ? S102 P102 S103 120.18(5) . . ? N100 P102 P101 41.01(8) . . ? C109 P102 P101 89.58(9) . . ? S102 P102 P101 151.51(4) . . ? S103 P102 P101 53.42(3) . . ? P1 N P2 97.95(12) . . ? P1 N Si 126.63(14) . . ? P2 N Si 133.18(15) . . ? P101 N100 P102 97.85(12) . . ? P101 N100 Si10 130.60(13) . . ? P102 N100 Si10 129.27(14) . . ? C2 C1 C10 120.7(3) . . ? C2 C1 P1 121.5(2) . . ? C10 C1 P1 117.8(2) . . ? C1 C2 C3 120.3(3) . . ? C4 C3 C2 120.3(3) . . ? C3 C4 C5 121.3(3) . . ? C4 C5 C6 121.4(3) . . ? C4 C5 C10 119.6(3) . . ? C6 C5 C10 119.0(3) . . ? C5 C10 C9 118.2(3) . . ? C5 C10 C1 117.8(3) . . ? C9 C10 C1 124.0(3) . . ? C8 C9 C10 120.8(3) . . ? C8 C9 P2 120.8(3) . . ? C10 C9 P2 118.4(2) . . ? C9 C8 C7 120.3(4) . . ? C6 C7 C8 120.4(4) . . ? C7 C6 C5 121.4(3) . . ? C102 C101 C110 120.5(3) . . ? C102 C101 P101 121.2(2) . . ? C110 C101 P101 118.4(2) . . ? C101 C102 C103 120.9(3) . . ? C104 C103 C102 120.1(3) . . ? C103 C104 C105 120.6(3) . . ? C104 C105 C106 120.6(3) . . ? C104 C105 C110 120.1(3) . . ? C106 C105 C110 119.2(3) . . ? C105 C110 C101 117.8(3) . . ? C105 C110 C109 118.7(3) . . ? C101 C110 C109 123.6(2) . . ? C108 C109 C110 119.8(3) . . ? C108 C109 P102 121.7(2) . . ? C110 C109 P102 118.5(2) . . ? C109 C108 C107 120.5(3) . . ? C106 C107 C108 120.6(3) . . ? C107 C106 C105 121.1(3) . . ? _diffrn_reflns_theta_full 25.05 _refine_diff_density_max .538 _refine_diff_density_min -.544 _refine_diff_density_rms .085 #=END data_3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,4-(4-methoxonaphthalene-1,8-diyl)-3-trimethyl silyl-1,3,2,4-thiazadiphosphetidine-2,4- disulfide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 N O P2 S3 Si' _chemical_formula_weight 401.50 _chemical_melting_point '442-444 K' _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' .0817 .0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _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 7.984(2) _cell_length_b 20.430(3) _cell_length_c 11.142(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.53(2) _cell_angle_gamma 90.00 _cell_volume 1797.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.484 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 832 _exptl_absorpt_coefficient_mu 0.656 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6217 _exptl_absorpt_correction_T_max 0.8274 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3297 _diffrn_reflns_av_R_equivalents 0.0603 _diffrn_reflns_av_sigmaI/netI 0.0510 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 25.11 _reflns_number_total 3139 _reflns_number_gt 2326 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+3.1648P] 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 3139 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0476 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.02758(13) 0.30071(5) 0.18666(9) 0.0195(3) Uani 1 d . . . P2 P 0.13440(14) 0.39497(5) 0.32566(9) 0.0202(3) Uani 1 d . . . S1 S -0.00116(15) 0.21063(5) 0.14294(10) 0.0259(3) Uani 1 d . . . S2 S 0.24727(15) 0.43140(6) 0.47322(10) 0.0296(3) Uani 1 d . . . S3 S 0.27156(13) 0.34473(5) 0.20554(10) 0.0247(3) Uani 1 d . . . Si Si -0.14822(14) 0.31415(5) 0.42268(10) 0.0201(3) Uani 1 d . . . O O -0.3853(4) 0.48924(15) -0.1349(3) 0.0318(7) Uani 1 d . . . N N 0.0106(4) 0.32804(16) 0.3276(3) 0.0197(7) Uani 1 d . . . C1 C -0.0996(5) 0.35659(19) 0.0895(4) 0.0194(8) Uani 1 d . . . C2 C -0.1989(5) 0.3351(2) -0.0136(4) 0.0232(9) Uani 1 d . . . C3 C -0.2983(6) 0.3784(2) -0.0910(4) 0.0256(9) Uani 1 d . . . C4 C -0.2978(5) 0.4441(2) -0.0638(4) 0.0245(9) Uani 1 d . . . C5 C -0.1970(5) 0.4687(2) 0.0431(4) 0.0210(9) Uani 1 d . . . C10 C -0.0968(5) 0.42465(19) 0.1207(3) 0.0190(8) Uani 1 d . . . C9 C 0.0049(5) 0.45055(19) 0.2258(4) 0.0188(8) Uani 1 d . . . C8 C 0.0024(5) 0.5158(2) 0.2512(4) 0.0235(9) Uani 1 d . . . C7 C -0.0964(6) 0.55897(19) 0.1731(4) 0.0266(10) Uani 1 d . . . C6 C -0.1940(6) 0.5357(2) 0.0712(4) 0.0252(9) Uani 1 d . . . C11 C -0.4746(6) 0.4671(3) -0.2493(4) 0.0349(11) Uani 1 d . . . C12 C -0.2580(7) 0.2377(2) 0.3734(4) 0.0377(12) Uani 1 d . . . C13 C -0.0346(7) 0.3057(3) 0.5784(4) 0.0384(12) Uani 1 d . . . C14 C -0.2896(7) 0.3851(3) 0.4053(5) 0.0396(12) Uani 1 d . . . H8 H 0.0716 0.5303 0.3206 0.015 Uiso 1 d . . . H3 H -0.3658 0.3638 -0.1599 0.009 Uiso 1 d . . . H14C H -0.2225 0.4203 0.4369 0.027 Uiso 1 d . . . H11C H -0.5380 0.5069 -0.2888 0.038 Uiso 1 d . . . H14B H -0.3870 0.3798 0.4443 0.059 Uiso 1 d . . . H10 H -0.2662 0.5639 0.0148 0.015 Uiso 1 d . . . H12C H -0.3535 0.2398 0.4203 0.036 Uiso 1 d . . . H9 H -0.0894 0.6034 0.1837 0.018 Uiso 1 d . . . H2 H -0.1935 0.2899 -0.0386 0.043 Uiso 1 d . . . H12B H -0.3298 0.2475 0.2898 0.061 Uiso 1 d . . . H11B H -0.3981 0.4415 -0.3248 0.107 Uiso 1 d . . . H12A H -0.1834 0.2034 0.3741 0.106 Uiso 1 d . . . H11A H -0.5855 0.4249 -0.2389 0.047 Uiso 1 d . . . H14A H -0.3613 0.3834 0.3180 0.094 Uiso 1 d . . . H13A H 0.0463 0.2859 0.5772 0.123 Uiso 1 d . . . H13C H -0.1160 0.2929 0.6272 0.068 Uiso 1 d . . . H13B H 0.0235 0.3404 0.5929 0.079 Uiso 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 0.0206(6) 0.0190(5) 0.0192(6) -0.0002(4) 0.0044(4) 0.0014(4) P2 0.0181(6) 0.0210(5) 0.0212(5) -0.0006(4) 0.0018(4) -0.0008(4) S1 0.0351(6) 0.0194(5) 0.0241(6) -0.0010(4) 0.0072(5) 0.0014(4) S2 0.0298(6) 0.0305(6) 0.0256(6) -0.0022(4) -0.0054(5) -0.0039(5) S3 0.0194(6) 0.0263(5) 0.0293(6) -0.0007(4) 0.0068(4) 0.0024(4) Si 0.0194(6) 0.0227(6) 0.0183(6) -0.0012(4) 0.0027(4) -0.0004(4) O 0.0302(17) 0.0293(16) 0.0326(17) 0.0042(13) -0.0067(13) 0.0024(14) N 0.0218(18) 0.0216(17) 0.0158(16) -0.0011(13) 0.0029(13) -0.0002(14) C1 0.020(2) 0.0201(19) 0.0185(19) -0.0002(15) 0.0044(16) 0.0000(15) C2 0.027(2) 0.0191(19) 0.023(2) -0.0007(16) 0.0013(17) -0.0017(17) C3 0.024(2) 0.027(2) 0.023(2) -0.0007(17) -0.0032(17) 0.0006(18) C4 0.019(2) 0.028(2) 0.025(2) 0.0066(17) -0.0006(17) 0.0018(17) C5 0.018(2) 0.022(2) 0.024(2) 0.0033(16) 0.0055(16) -0.0012(16) C10 0.017(2) 0.023(2) 0.018(2) -0.0005(15) 0.0051(16) 0.0009(16) C9 0.017(2) 0.0204(19) 0.0194(19) 0.0001(15) 0.0054(16) -0.0014(16) C8 0.023(2) 0.027(2) 0.021(2) -0.0022(16) 0.0042(17) -0.0024(18) C7 0.030(2) 0.0174(19) 0.033(2) -0.0022(17) 0.0064(19) -0.0001(17) C6 0.023(2) 0.026(2) 0.027(2) 0.0033(17) 0.0050(18) 0.0010(17) C11 0.028(3) 0.046(3) 0.027(2) 0.005(2) -0.008(2) 0.003(2) C12 0.039(3) 0.041(3) 0.036(3) -0.006(2) 0.014(2) -0.017(2) C13 0.035(3) 0.059(3) 0.021(2) -0.002(2) 0.004(2) -0.013(2) C14 0.032(3) 0.038(3) 0.053(3) 0.009(2) 0.018(2) 0.012(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 N 1.691(3) . ? P1 C1 1.783(4) . ? P1 S1 1.9089(14) . ? P1 S3 2.1274(16) . ? P1 P2 2.5381(15) . ? P2 N 1.689(3) . ? P2 C9 1.804(4) . ? P2 S2 1.9051(15) . ? P2 S3 2.1164(16) . ? Si N 1.792(4) . ? Si C14 1.830(5) . ? Si C12 1.835(5) . ? Si C13 1.842(5) . ? O C4 1.342(5) . ? O C11 1.438(5) . ? C1 C2 1.368(6) . ? C1 C10 1.432(5) . ? C2 C3 1.398(6) . ? C3 C4 1.375(6) . ? C4 C5 1.426(6) . ? C5 C6 1.402(6) . ? C5 C10 1.412(6) . ? C10 C9 1.425(6) . ? C9 C8 1.364(6) . ? C8 C7 1.397(6) . ? C7 C6 1.364(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 N P1 C1 103.62(18) . . ? N P1 S1 122.15(13) . . ? C1 P1 S1 115.23(14) . . ? N P1 S3 88.10(13) . . ? C1 P1 S3 102.71(14) . . ? S1 P1 S3 120.42(7) . . ? N P1 P2 41.30(12) . . ? C1 P1 P2 89.67(14) . . ? S1 P1 P2 154.68(7) . . ? S3 P1 P2 53.07(5) . . ? N P2 C9 103.57(18) . . ? N P2 S2 120.54(13) . . ? C9 P2 S2 116.14(14) . . ? N P2 S3 88.51(12) . . ? C9 P2 S3 102.61(14) . . ? S2 P2 S3 120.82(7) . . ? N P2 P1 41.35(11) . . ? C9 P2 P1 89.51(13) . . ? S2 P2 P1 153.65(7) . . ? S3 P2 P1 53.47(5) . . ? P2 S3 P1 73.46(5) . . ? N Si C14 107.0(2) . . ? N Si C12 107.83(19) . . ? C14 Si C12 112.5(3) . . ? N Si C13 106.2(2) . . ? C14 Si C13 112.6(3) . . ? C12 Si C13 110.4(2) . . ? C4 O C11 117.0(4) . . ? P2 N P1 97.35(18) . . ? P2 N Si 127.0(2) . . ? P1 N Si 131.2(2) . . ? C2 C1 C10 120.1(4) . . ? C2 C1 P1 120.7(3) . . ? C10 C1 P1 119.2(3) . . ? C1 C2 C3 121.3(4) . . ? C4 C3 C2 120.0(4) . . ? O C4 C3 123.8(4) . . ? O C4 C5 115.5(4) . . ? C3 C4 C5 120.7(4) . . ? C6 C5 C10 119.7(4) . . ? C6 C5 C4 121.3(4) . . ? C10 C5 C4 119.0(4) . . ? C5 C10 C9 118.0(4) . . ? C5 C10 C1 118.9(4) . . ? C9 C10 C1 123.1(4) . . ? C8 C9 C10 120.6(4) . . ? C8 C9 P2 120.8(3) . . ? C10 C9 P2 118.5(3) . . ? C9 C8 C7 120.8(4) . . ? C6 C7 C8 119.9(4) . . ? C7 C6 C5 121.0(4) . . ? _diffrn_reflns_theta_full 25.11 _refine_diff_density_max .590 _refine_diff_density_min -.611 _refine_diff_density_rms .105 #=END data_4 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19.50 H37 Cl N2 P2 S4 Si3' _chemical_formula_weight 609.41 _chemical_melting_point 'decomp. above 393 K' _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Si' 'Si' .0817 .0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' .1023 .0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' .1484 .1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.698(9) _cell_length_b 12.841(3) _cell_length_c 14.008(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.08(4) _cell_angle_gamma 90.00 _cell_volume 3087.8(19) _cell_formula_units_Z 4 _cell_measurement_temperature 133(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.70 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1284 _exptl_absorpt_coefficient_mu 0.627 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.6338 _exptl_absorpt_correction_T_max 0.7875 _exptl_special_details ; ? ; _diffrn_ambient_temperature 133(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4736 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.09 _reflns_number_total 4591 _reflns_number_gt 3979 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+7.0000P] 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_number_reflns 4591 _refine_ls_number_parameters 440 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0402 _refine_ls_wR_factor_ref 0.1143 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 0.980 _refine_ls_restrained_S_all 0.980 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S3 S 0.31126(6) -0.25992(9) 0.00543(8) 0.0432(3) Uani 1 d . . . S4 S 0.20426(5) -0.30870(7) 0.16886(6) 0.0288(2) Uani 1 d . . . S1 S 0.30960(5) -0.49337(8) 0.08404(6) 0.0286(2) Uani 1 d . . . S2 S 0.27220(5) -0.73338(8) 0.12460(6) 0.0341(2) Uani 1 d . . . P1 P 0.24257(5) -0.35587(8) 0.05465(6) 0.0261(2) Uani 1 d . . . P2 P 0.22905(5) -0.59397(7) 0.12118(6) 0.0230(2) Uani 1 d . . . Si1 Si 0.22795(5) -0.62114(8) 0.33950(6) 0.0263(2) Uani 1 d . . . Si2 Si 0.32824(6) -0.02834(8) 0.24578(7) 0.0297(2) Uani 1 d . . . Si3 Si 0.44597(5) -0.22633(10) 0.32537(7) 0.0364(3) Uani 1 d . . . N1 N 0.21152(18) -0.5591(3) 0.2253(2) 0.0281(7) Uani 1 d . . . N2 N 0.34985(16) -0.1630(3) 0.2910(2) 0.0271(7) Uani 1 d . . . C1 C 0.15967(19) -0.3961(3) -0.0419(2) 0.0249(7) Uani 1 d . . . C2 C 0.1330(2) -0.3226(3) -0.1133(3) 0.0347(9) Uani 1 d . . . C3 C 0.0641(2) -0.3361(4) -0.1867(3) 0.0434(11) Uani 1 d . . . C4 C 0.0219(2) -0.4233(3) -0.1861(3) 0.0357(9) Uani 1 d . . . C5 C 0.04630(18) -0.5020(3) -0.1148(2) 0.0260(8) Uani 1 d . . . C10 C 0.11785(17) -0.4907(3) -0.0409(2) 0.0235(7) Uani 1 d . . . C9 C 0.13931(18) -0.5761(3) 0.0268(2) 0.0237(7) Uani 1 d . . . C8 C 0.0891(2) -0.6582(3) 0.0232(3) 0.0295(8) Uani 1 d . . . C7 C 0.0175(2) -0.6634(3) -0.0468(3) 0.0344(9) Uani 1 d . . . C6 C -0.00204(19) -0.5884(3) -0.1154(3) 0.0321(9) Uani 1 d . . . C11A C 0.1885(2) -0.5282(4) 0.4164(3) 0.0409(10) Uani 1 d . . . C12 C 0.1731(3) -0.7443(4) 0.3255(3) 0.0441(11) Uani 1 d . . . C13 C 0.3331(2) -0.6417(4) 0.3922(3) 0.0348(9) Uani 1 d . . . C14 C 0.3719(4) 0.0580(4) 0.3480(4) 0.0560(13) Uani 1 d . . . C15 C 0.2221(3) -0.0193(5) 0.2110(6) 0.0602(15) Uani 1 d . . . C16 C 0.3701(3) -0.0079(5) 0.1405(4) 0.0499(12) Uani 1 d . . . C17 C 0.5013(3) -0.1574(5) 0.4350(4) 0.0562(14) Uani 1 d . . . C18 C 0.4240(3) -0.3618(4) 0.3514(5) 0.0569(13) Uani 1 d . . . C19 C 0.4923(4) -0.2185(9) 0.2226(5) 0.086(3) Uani 1 d . . . H1 H 0.206(2) -0.503(3) 0.225(3) 0.014(11) Uiso 1 d . . . H2 H 0.161(2) -0.269(3) -0.109(3) 0.028(11) Uiso 1 d . . . H2A H 0.332(2) -0.168(3) 0.346(3) 0.048(12) Uiso 1 d . . . H2B H 0.321(3) -0.198(4) 0.252(3) 0.045(13) Uiso 1 d . . . H6 H 0.049(3) -0.290(4) -0.236(4) 0.073(16) Uiso 1 d . . . H7 H -0.025(3) -0.438(4) -0.236(3) 0.060(13) Uiso 1 d . . . H8 H 0.107(2) -0.722(3) 0.069(3) 0.029(9) Uiso 1 d . . . H9 H -0.011(3) -0.716(4) -0.043(3) 0.045(12) Uiso 1 d . . . H10 H -0.052(2) -0.596(3) -0.164(3) 0.042(11) Uiso 1 d . . . H11A H 0.220(3) -0.474(4) 0.422(4) 0.063(16) Uiso 1 d . . . H11B H 0.130(3) -0.509(4) 0.388(3) 0.061(14) Uiso 1 d . . . H11C H 0.191(3) -0.561(5) 0.470(4) 0.086(19) Uiso 1 d . . . H12A H 0.117(3) -0.735(4) 0.310(4) 0.075(16) Uiso 1 d . . . H12B H 0.182(4) -0.787(6) 0.278(5) 0.12(3) Uiso 1 d . . . H12C H 0.180(4) -0.780(5) 0.380(5) 0.11(2) Uiso 1 d . . . H13A H 0.362(3) -0.577(4) 0.410(3) 0.051(13) Uiso 1 d . . . H13B H 0.339(3) -0.676(4) 0.452(4) 0.064(15) Uiso 1 d . . . H13C H 0.358(2) -0.676(3) 0.353(3) 0.042(11) Uiso 1 d . . . H14A H 0.429(3) 0.051(4) 0.357(3) 0.055(14) Uiso 1 d . . . H14B H 0.359(3) 0.124(4) 0.332(3) 0.049(13) Uiso 1 d . . . H14C H 0.354(4) 0.042(5) 0.412(5) 0.11(2) Uiso 1 d . . . H15A H 0.207(3) 0.044(5) 0.182(4) 0.085(19) Uiso 1 d . . . H15B H 0.202(4) -0.074(7) 0.177(5) 0.12(3) Uiso 1 d . . . H15C H 0.204(4) -0.027(5) 0.266(4) 0.09(2) Uiso 1 d . . . H16A H 0.425(4) -0.015(5) 0.158(4) 0.09(2) Uiso 1 d . . . H16B H 0.353(3) 0.058(5) 0.117(4) 0.069(17) Uiso 1 d . . . H16C H 0.353(3) -0.060(5) 0.102(4) 0.08(2) Uiso 1 d . . . H17A H 0.543(4) -0.191(5) 0.449(4) 0.082(19) Uiso 1 d . . . H17B H 0.517(3) -0.099(5) 0.409(4) 0.09(2) Uiso 1 d . . . H17C H 0.474(3) -0.158(4) 0.481(4) 0.074(18) Uiso 1 d . . . H18A H 0.465(3) -0.397(4) 0.383(4) 0.074(17) Uiso 1 d . . . H18B H 0.408(5) -0.396(7) 0.291(7) 0.16(4) Uiso 1 d . . . H18C H 0.395(4) -0.351(5) 0.399(4) 0.09(2) Uiso 1 d . . . H19A H 0.529(4) -0.272(5) 0.238(5) 0.10(2) Uiso 1 d . . . H19B H 0.465(3) -0.234(4) 0.161(4) 0.075(17) Uiso 1 d . . . H19C H 0.514(5) -0.158(7) 0.231(6) 0.13(4) Uiso 1 d . . . Cl Cl 0.02037(9) 0.07508(18) 0.08230(15) 0.1013(6) Uani 1 d . . . C11 C 0.0256(7) -0.0347(14) 0.0488(10) 0.086(6) Uani 0.50 d P . . H20A H 0.014(5) -0.081(8) 0.061(6) 0.030 Uiso 0.50 d P . . H20B H 0.061(5) -0.061(6) 0.048(6) 0.02(2) Uiso 0.50 d P . . 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 S3 0.0458(5) 0.0374(7) 0.0518(6) -0.0086(5) 0.0225(5) -0.0202(5) S4 0.0278(4) 0.0276(6) 0.0310(4) -0.0116(4) 0.0072(3) -0.0048(4) S1 0.0229(4) 0.0337(6) 0.0291(4) -0.0055(4) 0.0062(3) -0.0002(4) S2 0.0458(5) 0.0276(6) 0.0285(4) -0.0010(4) 0.0081(4) 0.0127(4) P1 0.0261(4) 0.0239(6) 0.0282(4) -0.0057(4) 0.0066(3) -0.0059(4) P2 0.0264(4) 0.0235(6) 0.0190(4) -0.0025(3) 0.0054(3) 0.0024(3) Si1 0.0295(5) 0.0305(7) 0.0191(4) 0.0008(4) 0.0061(3) 0.0009(4) Si2 0.0366(5) 0.0216(6) 0.0303(5) -0.0021(4) 0.0072(4) -0.0075(4) Si3 0.0241(5) 0.0503(8) 0.0324(5) -0.0013(5) 0.0026(4) 0.0064(5) N1 0.0429(18) 0.023(2) 0.0189(14) -0.0015(13) 0.0078(11) 0.0075(15) N2 0.0236(14) 0.029(2) 0.0268(15) -0.0038(13) 0.0018(12) -0.0038(13) C1 0.0311(17) 0.020(2) 0.0229(15) -0.0024(14) 0.0057(13) -0.0014(14) C2 0.042(2) 0.027(3) 0.0341(19) 0.0026(17) 0.0066(15) -0.0031(19) C3 0.051(2) 0.046(3) 0.0288(19) 0.0098(19) 0.0011(16) 0.011(2) C4 0.0312(18) 0.045(3) 0.0272(17) -0.0027(16) -0.0005(14) 0.0071(18) C5 0.0267(16) 0.026(2) 0.0240(15) -0.0068(14) 0.0040(13) 0.0032(15) C10 0.0221(15) 0.030(2) 0.0192(14) -0.0065(14) 0.0056(12) 0.0000(14) C9 0.0262(16) 0.026(2) 0.0202(15) -0.0065(13) 0.0080(12) -0.0012(14) C8 0.0331(18) 0.027(2) 0.0310(17) -0.0029(16) 0.0129(14) -0.0050(16) C7 0.0291(18) 0.031(3) 0.045(2) -0.0113(18) 0.0138(16) -0.0112(17) C6 0.0234(16) 0.039(3) 0.0319(18) -0.0164(17) 0.0029(14) -0.0010(16) C11A 0.038(2) 0.058(3) 0.0271(19) -0.005(2) 0.0092(16) 0.008(2) C12 0.053(3) 0.046(3) 0.037(2) 0.004(2) 0.0155(19) -0.014(2) C13 0.0346(19) 0.041(3) 0.0282(19) -0.0011(18) 0.0071(15) 0.0037(18) C14 0.095(4) 0.027(3) 0.042(2) -0.008(2) 0.009(2) -0.005(3) C15 0.044(3) 0.030(3) 0.106(5) 0.023(3) 0.017(3) 0.006(2) C16 0.074(3) 0.036(3) 0.045(2) 0.003(2) 0.024(2) -0.002(3) C17 0.029(2) 0.073(4) 0.055(3) -0.005(3) -0.012(2) -0.009(2) C18 0.051(3) 0.042(3) 0.072(3) -0.002(3) 0.004(2) 0.026(2) C19 0.054(3) 0.157(9) 0.054(3) 0.024(4) 0.023(3) 0.053(5) Cl 0.0688(9) 0.1028(16) 0.1240(15) 0.0479(12) 0.0074(9) -0.0249(9) C11 0.041(6) 0.123(16) 0.090(9) 0.092(10) 0.011(6) 0.006(7) _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 S3 P1 1.9696(14) . ? S4 P1 1.9784(13) . ? S1 P2 2.0815(14) . ? S1 P1 2.1110(14) . ? S2 P2 1.9423(13) . ? P1 C1 1.812(3) . ? P2 N1 1.626(3) . ? P2 C9 1.817(3) . ? Si1 N1 1.748(3) . ? Si1 C12 1.841(5) . ? Si1 C13 1.846(4) . ? Si1 C11A 1.854(4) . ? Si2 C16 1.823(5) . ? Si2 C15 1.825(5) . ? Si2 C14 1.827(5) . ? Si2 N2 1.850(3) . ? Si3 C19 1.825(6) . ? Si3 C17 1.835(5) . ? Si3 C18 1.838(6) . ? Si3 N2 1.840(3) . ? C1 C2 1.372(5) . ? C1 C10 1.424(5) . ? C2 C3 1.402(6) . ? C3 C4 1.347(6) . ? C4 C5 1.413(5) . ? C5 C6 1.400(5) . ? C5 C10 1.434(4) . ? C10 C9 1.438(5) . ? C9 C8 1.372(5) . ? C8 C7 1.403(5) . ? C7 C6 1.345(6) . ? Cl C11 1.50(2) . ? Cl C11 1.891(16) 3 ? C11 C11 1.696(19) 3 ? C11 Cl 1.891(16) 3 ? 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 P2 S1 P1 100.44(6) . . ? C1 P1 S3 111.94(12) . . ? C1 P1 S4 108.46(12) . . ? S3 P1 S4 116.98(6) . . ? C1 P1 S1 102.79(12) . . ? S3 P1 S1 103.07(6) . . ? S4 P1 S1 112.66(6) . . ? N1 P2 C9 107.10(15) . . ? N1 P2 S2 113.06(15) . . ? C9 P2 S2 113.79(12) . . ? N1 P2 S1 110.17(14) . . ? C9 P2 S1 105.67(12) . . ? S2 P2 S1 106.80(6) . . ? N1 Si1 C12 109.18(19) . . ? N1 Si1 C13 111.00(17) . . ? C12 Si1 C13 112.0(2) . . ? N1 Si1 C11A 103.6(2) . . ? C12 Si1 C11A 110.6(2) . . ? C13 Si1 C11A 110.20(19) . . ? C16 Si2 C15 111.7(3) . . ? C16 Si2 C14 111.7(3) . . ? C15 Si2 C14 112.5(3) . . ? C16 Si2 N2 108.7(2) . . ? C15 Si2 N2 105.3(2) . . ? C14 Si2 N2 106.6(2) . . ? C19 Si3 C17 112.5(4) . . ? C19 Si3 C18 111.5(4) . . ? C17 Si3 C18 112.7(3) . . ? C19 Si3 N2 109.5(2) . . ? C17 Si3 N2 106.1(2) . . ? C18 Si3 N2 104.09(19) . . ? P2 N1 Si1 132.1(2) . . ? Si3 N2 Si2 127.13(17) . . ? C2 C1 C10 120.5(3) . . ? C2 C1 P1 114.8(3) . . ? C10 C1 P1 124.3(2) . . ? C1 C2 C3 122.2(4) . . ? C4 C3 C2 118.8(4) . . ? C3 C4 C5 121.7(3) . . ? C6 C5 C4 118.8(3) . . ? C6 C5 C10 121.0(3) . . ? C4 C5 C10 120.1(3) . . ? C1 C10 C5 116.6(3) . . ? C1 C10 C9 127.0(3) . . ? C5 C10 C9 116.4(3) . . ? C8 C9 C10 119.8(3) . . ? C8 C9 P2 111.9(3) . . ? C10 C9 P2 128.3(2) . . ? C9 C8 C7 122.0(4) . . ? C6 C7 C8 119.7(4) . . ? C7 C6 C5 120.8(3) . . ? C11 Cl C11 58.7(6) . 3 ? Cl C11 C11 72.3(13) . 3 ? Cl C11 Cl 121.3(6) . 3 ? C11 C11 Cl 48.9(10) 3 3 ? _diffrn_reflns_theta_full 25.09 _refine_diff_density_max .349 _refine_diff_density_min -.554 _refine_diff_density_rms .075