# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 186/1471 data_global _publ_requested_journal 'Dalton Trans.' _publ_contact_author ; J.D.Woollins Dept. of Chemistry, Loughborough Univ., Loughborough, Leics LE11 3TU ; _publ_contact_author_email ' J.D.Woollins@lboro.ac.uk ' data_3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H27 N P2 S4 Si2' _chemical_formula_weight 491.76 _chemical_melting_point 156-8 _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' 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' 'Si' 'Si' 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' '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 7.178(2) _cell_length_b 10.502(3) _cell_length_c 17.184(5) _cell_angle_alpha 105.81(2) _cell_angle_beta 93.25(2) _cell_angle_gamma 100.94(2) _cell_volume 1215.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 36 _cell_measurement_theta_min 10 _cell_measurement_theta_max 13 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method ? _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.625 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4439 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.24 _diffrn_reflns_theta_max 25.05 _reflns_number_total 4289 _reflns_number_observed 3609 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0730P)^2^+1.3088P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4289 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_obs 0.0430 _refine_ls_wR_factor_all 0.1232 _refine_ls_wR_factor_obs 0.1140 _refine_ls_goodness_of_fit_all 1.018 _refine_ls_goodness_of_fit_obs 1.034 _refine_ls_restrained_S_all 1.018 _refine_ls_restrained_S_obs 1.034 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.10083(12) 0.30752(7) 0.35061(5) 0.0304(2) Uani 1 d . . S1' S 0.45301(10) 0.14533(7) 0.28074(5) 0.0292(2) Uani 1 d . . S19 S -0.02187(10) -0.00422(7) 0.24119(4) 0.02187(18) Uani 1 d . . S9 S -0.14619(11) -0.32802(7) 0.17301(5) 0.0312(2) Uani 1 d . . P1 P 0.18950(10) 0.13944(7) 0.32467(4) 0.02005(18) Uani 1 d . . P9 P 0.06757(10) -0.18656(7) 0.23398(4) 0.01907(18) Uani 1 d . . Si1 Si 0.50522(13) 0.32036(8) 0.23318(5) 0.0298(2) Uani 1 d . . Si9 Si 0.28288(11) -0.21691(8) 0.08600(5) 0.0250(2) Uani 1 d . . N9 N 0.2707(3) -0.1860(2) 0.19343(13) 0.0223(5) Uani 1 d . . C1 C 0.2190(4) 0.0721(3) 0.41037(16) 0.0198(5) Uani 1 d . . C2 C 0.2798(4) 0.1728(3) 0.48291(19) 0.0272(6) Uani 1 d . . C3 C 0.3097(4) 0.1444(3) 0.55651(19) 0.0295(7) Uani 1 d . . C4 C 0.2798(4) 0.0143(3) 0.55794(17) 0.0274(6) Uani 1 d . . C5 C 0.2185(4) -0.0935(3) 0.48563(17) 0.0226(6) Uani 1 d . . C10 C 0.1843(4) -0.0681(3) 0.40845(16) 0.0197(5) Uani 1 d . . C9 C 0.1183(4) -0.1839(3) 0.33923(17) 0.0211(6) Uani 1 d . . C8 C 0.0891(5) -0.3126(3) 0.3489(2) 0.0322(7) Uani 1 d . . C7 C 0.1253(6) -0.3345(3) 0.4243(2) 0.0371(8) Uani 1 d . . C6 C 0.1885(5) -0.2269(3) 0.4910(2) 0.0326(7) Uani 1 d . . C11 C 0.4403(5) -0.1960(4) 0.2396(2) 0.0302(7) Uani 1 d . . C12 C 0.2742(7) -0.3997(4) 0.0415(2) 0.0433(9) Uani 1 d . . C13 C 0.5186(5) -0.1189(4) 0.0744(2) 0.0396(8) Uani 1 d . . C14 C 0.0917(6) -0.1583(6) 0.0378(2) 0.0486(10) Uani 1 d . . C15 C 0.7178(5) 0.2895(4) 0.1801(2) 0.0366(8) Uani 1 d . . C17 C 0.5689(8) 0.4779(4) 0.3176(3) 0.0600(14) Uani 1 d . . C16 C 0.3021(8) 0.3133(8) 0.1598(4) 0.0675(16) Uani 1 d . . H2 H 0.2978(49) 0.2499(37) 0.4841(21) 0.028(9) Uiso 1 d . . H3 H 0.3556(54) 0.2161(40) 0.6055(24) 0.041(10) Uiso 1 d . . H4 H 0.2936(46) -0.0163(33) 0.6056(20) 0.026(8) Uiso 1 d . . H8 H 0.0322(54) -0.3928(40) 0.2987(24) 0.043(10) Uiso 1 d . . H9 H 0.1133(63) -0.4183(46) 0.4297(27) 0.059(13) Uiso 1 d . . H10 H 0.2225(53) -0.2400(37) 0.5455(23) 0.040(10) Uiso 1 d . . H11A H 0.4588(66) -0.1461(48) 0.2918(31) 0.061(13) Uiso 1 d . . H11B H 0.5424(84) -0.1671(56) 0.2199(34) 0.085(17) Uiso 1 d . . H11C H 0.4447(80) -0.2876(62) 0.2305(34) 0.088(18) Uiso 1 d . . H12A H 0.2502(80) -0.4177(56) -0.0105(38) 0.083(17) Uiso 1 d . . H12B H 0.3876(69) -0.4294(45) 0.0614(27) 0.058(13) Uiso 1 d . . H12C H 0.1527(96) -0.4411(62) 0.0470(37) 0.102(21) Uiso 1 d . . H13A H 0.6053(70) -0.1553(49) 0.0921(29) 0.065(15) Uiso 1 d . . H13B H 0.5213(62) -0.1237(44) 0.0239(29) 0.053(12) Uiso 1 d . . H13C H 0.5465(93) -0.0114(71) 0.1067(40) 0.119(23) Uiso 1 d . . H14A H 0.0882(72) -0.0793(53) 0.0666(32) 0.066(16) Uiso 1 d . . H14B H 0.0937(68) -0.1684(49) -0.0141(33) 0.067(14) Uiso 1 d . . H14C H -0.0300(89) -0.2083(57) 0.0352(34) 0.086(18) Uiso 1 d . . H15A H 0.7647(76) 0.3716(56) 0.1658(32) 0.082(16) Uiso 1 d . . H15B H 0.6878(66) 0.2152(50) 0.1316(30) 0.064(13) Uiso 1 d . . H15C H 0.8182(59) 0.2718(41) 0.2172(25) 0.048(11) Uiso 1 d . . H16A H 0.6380(103) 0.5462(74) 0.2994(43) 0.126(24) Uiso 1 d . . H16B H 0.4658(74) 0.4963(47) 0.3428(30) 0.066(14) Uiso 1 d . . H16C H 0.6599(71) 0.4707(49) 0.3547(31) 0.061(16) Uiso 1 d . . H17A H 0.3491(88) 0.3769(64) 0.1303(39) 0.100(19) Uiso 1 d . . H17B H 0.2284(126) 0.3397(85) 0.1865(52) 0.138(32) Uiso 1 d . . H17C H 0.2522(135) 0.2350(96) 0.1261(57) 0.165(43) 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 0.0408(5) 0.0191(4) 0.0368(4) 0.0109(3) 0.0139(3) 0.0128(3) S1' 0.0257(4) 0.0249(4) 0.0439(4) 0.0182(3) 0.0155(3) 0.0064(3) S19 0.0203(3) 0.0215(4) 0.0250(4) 0.0065(3) 0.0049(3) 0.0070(3) S9 0.0245(4) 0.0233(4) 0.0379(4) 0.0000(3) 0.0042(3) -0.0013(3) P1 0.0217(4) 0.0155(3) 0.0252(4) 0.0082(3) 0.0081(3) 0.0044(3) P9 0.0190(4) 0.0167(3) 0.0212(4) 0.0040(3) 0.0073(3) 0.0039(3) Si1 0.0349(5) 0.0251(4) 0.0352(5) 0.0174(4) 0.0129(4) 0.0056(3) Si9 0.0261(4) 0.0308(4) 0.0200(4) 0.0069(3) 0.0061(3) 0.0103(3) N9 0.0286(12) 0.0225(12) 0.0180(11) 0.0056(9) 0.0096(9) 0.0088(10) C1 0.0172(13) 0.0194(13) 0.0243(14) 0.0085(11) 0.0061(10) 0.0031(10) C2 0.0284(16) 0.0172(15) 0.0337(16) 0.0057(12) 0.0034(12) 0.0016(12) C3 0.0297(16) 0.0295(16) 0.0247(15) 0.0017(13) -0.0005(12) 0.0055(13) C4 0.0279(15) 0.0356(17) 0.0216(14) 0.0103(13) 0.0083(12) 0.0090(13) C5 0.0204(14) 0.0269(15) 0.0254(14) 0.0119(12) 0.0117(11) 0.0078(11) C10 0.0186(13) 0.0196(13) 0.0235(13) 0.0081(11) 0.0123(10) 0.0049(10) C9 0.0223(14) 0.0200(13) 0.0244(14) 0.0089(11) 0.0134(11) 0.0059(11) C8 0.0482(19) 0.0183(14) 0.0330(17) 0.0081(13) 0.0176(14) 0.0092(13) C7 0.063(2) 0.0185(15) 0.0379(18) 0.0150(14) 0.0221(16) 0.0133(15) C6 0.0442(19) 0.0312(17) 0.0314(16) 0.0186(14) 0.0164(14) 0.0120(14) C11 0.0273(16) 0.0399(19) 0.0259(16) 0.0098(14) 0.0076(13) 0.0117(14) C12 0.054(2) 0.0365(19) 0.0326(19) -0.0028(15) 0.0105(17) 0.0100(18) C13 0.038(2) 0.051(2) 0.0333(19) 0.0210(17) 0.0137(15) 0.0042(17) C14 0.046(2) 0.085(3) 0.0277(19) 0.022(2) 0.0090(16) 0.036(2) C15 0.0379(19) 0.0357(18) 0.0406(19) 0.0180(16) 0.0160(15) 0.0051(15) C17 0.072(3) 0.0248(19) 0.072(3) 0.0025(19) 0.038(3) -0.008(2) C16 0.055(3) 0.114(5) 0.064(3) 0.062(4) 0.017(2) 0.035(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 S1 P1 1.9363(11) . ? S1' P1 2.0722(11) . ? S1' Si1 2.1862(12) . ? S19 P1 2.0835(12) . ? S19 P9 2.1073(11) . ? S9 P9 1.9399(12) . ? P1 C1 1.8175(27) . ? P9 N9 1.6508(24) . ? P9 C9 1.8162(29) . ? Si1 C17 1.8384(44) . ? Si1 C16 1.8500(51) . ? Si1 C15 1.8572(35) . ? Si9 N9 1.7953(23) . ? Si9 C14 1.8487(38) . ? Si9 C12 1.8506(38) . ? Si9 C13 1.8579(36) . ? N9 C11 1.4521(40) . ? C1 C2 1.3809(41) . ? C1 C10 1.4363(37) . ? C2 C3 1.3903(45) . ? C3 C4 1.3499(45) . ? C4 C5 1.4147(42) . ? C5 C6 1.4060(42) . ? C5 C10 1.4394(38) . ? C10 C9 1.4313(39) . ? C9 C8 1.3841(40) . ? C8 C7 1.3948(47) . ? C7 C6 1.3561(49) . ? 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 S1' Si1 106.29(5) . . ? P1 S19 P9 102.73(4) . . ? C1 P1 S1 114.48(10) . . ? C1 P1 S1' 102.61(9) . . ? S1 P1 S1' 116.28(5) . . ? C1 P1 S19 105.89(9) . . ? S1 P1 S19 106.58(5) . . ? S1' P1 S19 110.59(5) . . ? N9 P9 C9 106.88(12) . . ? N9 P9 S9 115.08(9) . . ? C9 P9 S9 114.57(10) . . ? N9 P9 S19 110.38(9) . . ? C9 P9 S19 104.63(9) . . ? S9 P9 S19 104.79(5) . . ? C17 Si1 C16 114.4(3) . . ? C17 Si1 C15 110.1(2) . . ? C16 Si1 C15 110.7(2) . . ? C17 Si1 S1' 110.12(18) . . ? C16 Si1 S1' 110.8(2) . . ? C15 Si1 S1' 99.76(12) . . ? N9 Si9 C14 111.41(15) . . ? N9 Si9 C12 107.90(16) . . ? C14 Si9 C12 112.8(2) . . ? N9 Si9 C13 106.52(15) . . ? C14 Si9 C13 109.1(2) . . ? C12 Si9 C13 109.0(2) . . ? C11 N9 P9 120.32(19) . . ? C11 N9 Si9 115.12(19) . . ? P9 N9 Si9 122.67(14) . . ? C2 C1 C10 120.5(3) . . ? C2 C1 P1 112.5(2) . . ? C10 C1 P1 127.0(2) . . ? C1 C2 C3 122.3(3) . . ? C4 C3 C2 119.5(3) . . ? C3 C4 C5 120.9(3) . . ? C6 C5 C4 118.3(3) . . ? C6 C5 C10 120.5(3) . . ? C4 C5 C10 121.2(3) . . ? C9 C10 C1 127.5(2) . . ? C9 C10 C5 116.9(2) . . ? C1 C10 C5 115.6(2) . . ? C8 C9 C10 119.8(3) . . ? C8 C9 P9 112.5(2) . . ? C10 C9 P9 127.7(2) . . ? C9 C8 C7 122.2(3) . . ? C6 C7 C8 119.5(3) . . ? C7 C6 C5 121.2(3) . . ? _refine_diff_density_max 0.705 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.094 #===END data_5 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C35 H30 N P3 S4' _chemical_formula_weight 685.75 _chemical_melting_point 195-7 _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' 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' 'P' 'P' 0.1023 0.0942 '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 9.8665(7) _cell_length_b 10.4165(8) _cell_length_c 17.1308(15) _cell_angle_alpha 105.217(8) _cell_angle_beta 102.994(7) _cell_angle_gamma 90.777(6) _cell_volume 1650.4(2) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rhomboid _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method ? _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.460 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8096 _diffrn_reflns_av_R_equivalents 0.0372 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5459 _reflns_number_observed 4755 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^+3.0000P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0132(15) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5459 _refine_ls_number_parameters 497 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_obs 0.0466 _refine_ls_wR_factor_all 0.1288 _refine_ls_wR_factor_obs 0.1196 _refine_ls_goodness_of_fit_all 1.010 _refine_ls_goodness_of_fit_obs 1.012 _refine_ls_restrained_S_all 1.010 _refine_ls_restrained_S_obs 1.012 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group S1 S 0.43802(8) 0.15467(8) 0.19751(5) 0.0371(2) Uani 1 d . . S1' S 0.35580(10) 0.30887(7) 0.37995(5) 0.0419(2) Uani 1 d . . S9 S -0.12739(9) -0.04313(12) 0.27066(7) 0.0591(3) Uani 1 d . . S19 S 0.13654(7) 0.07910(7) 0.22236(4) 0.0302(2) Uani 1 d . . P1 P 0.34689(8) 0.14615(7) 0.28725(4) 0.0273(2) Uani 1 d . . P9 P 0.05509(8) 0.05326(8) 0.32005(5) 0.0335(2) Uani 1 d . . N9 N 0.0474(5) 0.1970(4) 0.3878(2) 0.0537(10) Uani 1 d . . C1 C 0.4018(3) 0.0093(3) 0.33166(16) 0.0250(6) Uani 1 d . . C2 C 0.5338(3) -0.0275(3) 0.32853(19) 0.0324(6) Uani 1 d . . C3 C 0.5994(3) -0.1162(3) 0.3716(2) 0.0360(7) Uani 1 d . . C4 C 0.5318(3) -0.1656(3) 0.41928(19) 0.0337(7) Uani 1 d . . C5 C 0.3935(3) -0.1339(3) 0.42330(17) 0.0278(6) Uani 1 d . . C6 C 0.3277(3) -0.1873(3) 0.47409(19) 0.0341(7) Uani 1 d . . C7 C 0.1955(3) -0.1599(3) 0.4800(2) 0.0379(7) Uani 1 d . . C8 C 0.1215(3) -0.0842(3) 0.43160(19) 0.0339(7) Uani 1 d . . C9 C 0.1803(3) -0.0290(3) 0.38064(16) 0.0269(6) Uani 1 d . . C10 C 0.3232(3) -0.0481(3) 0.37722(16) 0.0252(6) Uani 1 d . . C11 C -0.0496(8) 0.2896(5) 0.3620(3) 0.107(2) Uani 1 d . . H11A H -0.0215 0.3209 0.3183 0.160 Uiso 1 calc R . H11B H -0.0493 0.3660 0.4098 0.160 Uiso 1 calc R . H11C H -0.1437 0.2446 0.3403 0.160 Uiso 1 calc R . P3 P 0.84552(8) 0.49687(7) 0.15494(4) 0.0270(2) Uani 1 d . . C12 C 1.0259(3) 0.5495(3) 0.17276(17) 0.0286(6) Uani 1 d . . C13 C 1.0682(3) 0.6730(3) 0.16803(19) 0.0348(7) Uani 1 d . . C14 C 1.2085(4) 0.7144(4) 0.1895(2) 0.0450(8) Uani 1 d . . C15 C 1.3065(4) 0.6340(4) 0.2165(2) 0.0500(9) Uani 1 d . . C16 C 1.2654(4) 0.5116(6) 0.2221(3) 0.0653(13) Uani 1 d . . C17 C 1.1256(4) 0.4674(4) 0.1998(3) 0.0531(10) Uani 1 d . . C18 C 0.7381(3) 0.5934(3) 0.09654(18) 0.0302(6) Uani 1 d . . C19 C 0.7403(6) 0.5839(6) 0.0161(3) 0.094(2) Uani 1 d . . H19 H 0.7968 0.5226 -0.0109 0.113 Uiso 1 calc R . C20 C 0.6603(7) 0.6637(7) -0.0265(3) 0.106(2) Uani 1 d . . H20 H 0.6624 0.6559 -0.0827 0.127 Uiso 1 calc R . C21 C 0.5803(4) 0.7514(4) 0.0100(3) 0.0542(10) Uani 1 d . . C22 C 0.5755(5) 0.7617(5) 0.0900(3) 0.0701(13) Uani 1 d . . C23 C 0.6559(5) 0.6831(5) 0.1339(3) 0.0633(12) Uani 1 d . . C24 C 0.8023(3) 0.5243(3) 0.25381(17) 0.0268(6) Uani 1 d . . C25 C 0.8920(3) 0.6050(3) 0.32467(19) 0.0331(6) Uani 1 d . . C26 C 0.8579(4) 0.6254(3) 0.4007(2) 0.0376(7) Uani 1 d . . C27 C 0.7377(4) 0.5646(3) 0.4069(2) 0.0392(7) Uani 1 d . . C28 C 0.6473(4) 0.4868(4) 0.3363(2) 0.0480(9) Uani 1 d . . C29 C 0.6771(3) 0.4685(4) 0.2598(2) 0.0422(8) Uani 1 d . . C30 C 0.8240(4) 0.3224(3) 0.1006(2) 0.0402(8) Uani 1 d . . C31_a C 0.9032(8) 0.2842(5) 0.0384(4) 0.0503(19) Uani 0.630(8) d P 1 H31_a H 0.9588 0.3490 0.0270 0.060 Uiso 0.630(8) calc PR 1 C32_a C 0.8963(9) 0.1502(6) -0.0046(4) 0.061(2) Uani 0.630(8) d P 1 H32_a H 0.9500 0.1204 -0.0446 0.073 Uiso 0.630(8) calc PR 1 C31_b C 0.7780(12) 0.2843(8) 0.0084(5) 0.043(3) Uani 0.370(8) d P 2 H31A_b H 0.7600 0.3512 -0.0203 0.052 Uiso 0.370(8) calc PR 2 C32_b C 0.7616(13) 0.1507(9) -0.0357(6) 0.051(3) Uani 0.370(8) d P 2 H32A_b H 0.7255 0.1224 -0.0943 0.062 Uiso 0.370(8) calc PR 2 C33 C 0.8032(6) 0.0557(4) 0.0135(3) 0.0765(15) Uani 1 d . . H33_a H 0.7675 -0.0275 -0.0254 0.092 Uiso 1 calc R 1 C34 C 0.7729(5) 0.0922(4) 0.0855(2) 0.0542(10) Uani 1 d . . C35 C 0.7816(5) 0.2262(4) 0.1296(2) 0.0529(10) Uani 1 d . . H1 H 0.1121(31) 0.2336(31) 0.4033(20) 0.010(9) Uiso 1 d . . H2 H 0.0266(37) -0.0729(32) 0.4296(20) 0.036(9) Uiso 1 d . . H3 H 0.1553(36) -0.1965(34) 0.5135(21) 0.038(9) Uiso 1 d . . H4 H 0.3828(35) -0.2510(34) 0.5036(21) 0.039(9) Uiso 1 d . . H8 H 0.5796(32) 0.0070(30) 0.2991(19) 0.025(7) Uiso 1 d . . H9 H 0.6957(44) -0.1354(39) 0.3685(24) 0.057(11) Uiso 1 d . . H10 H 0.5763(36) -0.2323(35) 0.4513(21) 0.042(9) Uiso 1 d . . H13 H 1.0052(38) 0.7261(36) 0.1520(22) 0.041(9) Uiso 1 d . . H14 H 1.2378(45) 0.7957(44) 0.1833(27) 0.064(13) Uiso 1 d . . H15 H 1.4063(46) 0.6682(40) 0.2328(25) 0.062(12) Uiso 1 d . . H16 H 1.3240(57) 0.4634(53) 0.2413(33) 0.089(16) Uiso 1 d . . H17 H 1.0906(44) 0.3872(43) 0.1966(26) 0.060(12) Uiso 1 d . . H21 H 0.5288(47) 0.8106(44) -0.0171(28) 0.069(13) Uiso 1 d . . H22 H 0.5270(58) 0.8250(56) 0.1201(34) 0.097(18) Uiso 1 d . . H23 H 0.6560(51) 0.6952(50) 0.1830(32) 0.078(16) Uiso 1 d . . H25 H 0.9756(40) 0.6495(37) 0.3168(23) 0.049(10) Uiso 1 d . . H26 H 0.9204(38) 0.6771(36) 0.4474(23) 0.041(9) Uiso 1 d . . H27 H 0.7156(36) 0.5733(34) 0.4575(23) 0.040(9) Uiso 1 d . . H28 H 0.5702(42) 0.4509(37) 0.3429(23) 0.048(10) Uiso 1 d . . H29 H 0.6091(43) 0.4167(40) 0.2088(26) 0.059(11) Uiso 1 d . . H34 H 0.7338(55) 0.0296(52) 0.1039(32) 0.089(16) Uiso 1 d . . H35 H 0.7484(46) 0.2513(45) 0.1737(29) 0.067(13) 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 0.0406(4) 0.0468(5) 0.0298(4) 0.0141(3) 0.0165(3) -0.0004(3) S1' 0.0748(6) 0.0247(4) 0.0288(4) 0.0060(3) 0.0189(4) 0.0009(4) S9 0.0236(4) 0.0938(8) 0.0808(7) 0.0556(6) 0.0167(4) 0.0129(4) S19 0.0303(4) 0.0354(4) 0.0296(4) 0.0119(3) 0.0127(3) 0.0087(3) P1 0.0346(4) 0.0265(4) 0.0239(4) 0.0077(3) 0.0123(3) 0.0014(3) P9 0.0326(4) 0.0384(4) 0.0415(4) 0.0193(4) 0.0223(3) 0.0157(3) N9 0.084(3) 0.0411(18) 0.059(2) 0.0234(17) 0.052(2) 0.030(2) C1 0.0296(14) 0.0224(12) 0.0228(13) 0.0038(11) 0.0088(11) 0.0008(11) C2 0.0328(16) 0.0331(15) 0.0332(15) 0.0075(13) 0.0139(13) -0.0009(12) C3 0.0279(16) 0.0382(16) 0.0421(17) 0.0095(14) 0.0103(13) 0.0071(13) C4 0.0321(16) 0.0322(15) 0.0344(15) 0.0064(13) 0.0059(13) 0.0060(12) C5 0.0318(15) 0.0212(13) 0.0263(13) 0.0019(11) 0.0038(11) -0.0012(11) C6 0.0386(17) 0.0330(15) 0.0312(15) 0.0129(13) 0.0045(13) -0.0019(13) C7 0.0414(18) 0.0431(17) 0.0361(16) 0.0212(14) 0.0115(14) -0.0027(14) C8 0.0306(16) 0.0398(16) 0.0344(16) 0.0113(13) 0.0126(13) 0.0002(13) C9 0.0298(15) 0.0276(14) 0.0238(13) 0.0046(11) 0.0099(11) 0.0039(11) C10 0.0283(14) 0.0233(13) 0.0212(12) 0.0004(10) 0.0068(11) -0.0014(11) C11 0.202(7) 0.087(4) 0.087(3) 0.064(3) 0.096(4) 0.103(4) P3 0.0296(4) 0.0244(4) 0.0274(4) 0.0071(3) 0.0073(3) 0.0042(3) C12 0.0283(15) 0.0348(15) 0.0257(13) 0.0115(12) 0.0083(11) 0.0075(12) C13 0.0350(17) 0.0278(15) 0.0372(16) 0.0024(13) 0.0071(13) 0.0067(13) C14 0.0354(18) 0.0390(18) 0.050(2) -0.0071(16) 0.0110(15) -0.0039(14) C15 0.0306(18) 0.083(3) 0.0349(17) 0.0142(18) 0.0075(14) 0.0033(18) C16 0.037(2) 0.116(4) 0.072(3) 0.067(3) 0.0205(19) 0.034(2) C17 0.039(2) 0.068(3) 0.079(3) 0.055(2) 0.0250(18) 0.0216(18) C18 0.0275(15) 0.0277(14) 0.0309(14) 0.0065(12) -0.0006(12) 0.0008(11) C19 0.108(4) 0.152(5) 0.045(2) 0.048(3) 0.033(2) 0.093(4) C20 0.128(5) 0.164(6) 0.055(3) 0.064(3) 0.035(3) 0.100(5) C21 0.045(2) 0.055(2) 0.058(2) 0.0280(19) -0.0123(17) 0.0067(17) C22 0.081(3) 0.063(3) 0.072(3) 0.028(2) 0.018(2) 0.041(2) C23 0.084(3) 0.067(3) 0.054(2) 0.032(2) 0.027(2) 0.046(2) C24 0.0278(14) 0.0283(14) 0.0268(13) 0.0086(11) 0.0098(11) 0.0086(11) C25 0.0385(17) 0.0256(14) 0.0360(16) 0.0043(12) 0.0157(13) 0.0020(12) C26 0.0422(18) 0.0318(16) 0.0344(16) -0.0015(13) 0.0128(15) 0.0033(14) C27 0.0459(19) 0.0412(17) 0.0387(17) 0.0120(14) 0.0247(15) 0.0136(14) C28 0.0304(18) 0.066(2) 0.053(2) 0.0187(19) 0.0187(16) 0.0015(16) C29 0.0263(16) 0.059(2) 0.0399(18) 0.0126(16) 0.0066(14) -0.0011(15) C30 0.062(2) 0.0250(15) 0.0342(16) 0.0048(13) 0.0166(15) 0.0042(14) C31_a 0.078(5) 0.033(3) 0.049(3) 0.015(3) 0.028(3) 0.010(3) C32_a 0.102(6) 0.038(3) 0.044(3) 0.004(3) 0.025(4) 0.022(3) C31_b 0.077(8) 0.027(4) 0.033(5) 0.011(4) 0.024(5) 0.006(4) C32_b 0.091(9) 0.037(5) 0.023(4) -0.004(4) 0.023(5) -0.004(5) C33 0.153(5) 0.0242(17) 0.048(2) 0.0028(16) 0.024(3) 0.006(2) C34 0.081(3) 0.0284(17) 0.048(2) 0.0081(16) 0.0084(19) -0.0054(17) C35 0.089(3) 0.0323(17) 0.0344(18) 0.0026(15) 0.0175(19) -0.0070(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 S1 P1 1.9675(10) . ? S1' P1 1.9806(10) . ? S9 P9 1.9456(13) . ? S19 P9 2.0867(10) . ? S19 P1 2.1323(11) . ? P1 C1 1.8191(27) . ? P9 N9 1.6507(35) . ? P9 C9 1.8045(29) . ? N9 C11 1.4500(55) . ? C1 C2 1.3711(41) . ? C1 C10 1.4399(37) . ? C2 C3 1.4048(44) . ? C3 C4 1.3545(45) . ? C4 C5 1.4201(41) . ? C5 C6 1.4095(41) . ? C5 C10 1.4301(39) . ? C6 C7 1.3595(46) . ? C7 C8 1.3885(45) . ? C8 C9 1.3828(40) . ? C9 C10 1.4386(38) . ? P3 C12 1.7897(29) . ? P3 C24 1.7908(27) . ? P3 C18 1.7933(29) . ? P3 C30 1.7965(30) . ? C12 C13 1.3750(43) . ? C12 C17 1.3929(43) . ? C13 C14 1.3815(47) . ? C14 C15 1.3689(53) . ? C15 C16 1.3664(64) . ? C16 C17 1.3831(58) . ? C18 C19 1.3602(50) . ? C18 C23 1.3712(49) . ? C19 C20 1.3867(58) . ? C20 C21 1.3381(64) . ? C21 C22 1.3580(63) . ? C22 C23 1.3923(54) . ? C24 C25 1.3875(42) . ? C24 C29 1.3939(43) . ? C25 C26 1.3809(43) . ? C26 C27 1.3749(46) . ? C27 C28 1.3764(52) . ? C28 C29 1.3726(49) . ? C30 C35 1.3289(50) . ? C30 C31_a 1.4368(66) . ? C30 C31_b 1.4841(94) . ? C31_a C32_a 1.3901(79) . ? C32_a C33 1.4740(89) . ? C31_b C32_b 1.3853(122) . ? C32_b C33 1.4675(112) . ? C33 C34 1.2943(60) . ? C34 C35 1.3930(50) . ? 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 P9 S19 P1 100.21(4) . . ? C1 P1 S1 112.19(9) . . ? C1 P1 S1' 108.18(9) . . ? S1 P1 S1' 118.79(5) . . ? C1 P1 S19 101.84(9) . . ? S1 P1 S19 103.18(4) . . ? S1' P1 S19 111.30(5) . . ? N9 P9 C9 102.58(17) . . ? N9 P9 S9 112.32(17) . . ? C9 P9 S9 115.43(10) . . ? N9 P9 S19 111.78(12) . . ? C9 P9 S19 107.67(9) . . ? S9 P9 S19 107.04(5) . . ? C11 N9 P9 118.6(4) . . ? C2 C1 C10 119.9(3) . . ? C2 C1 P1 115.7(2) . . ? C10 C1 P1 124.0(2) . . ? C1 C2 C3 122.3(3) . . ? C4 C3 C2 119.3(3) . . ? C3 C4 C5 120.9(3) . . ? C6 C5 C4 118.9(3) . . ? C6 C5 C10 120.7(3) . . ? C4 C5 C10 120.4(3) . . ? C7 C6 C5 121.1(3) . . ? C6 C7 C8 119.3(3) . . ? C9 C8 C7 122.2(3) . . ? C8 C9 C10 119.9(3) . . ? C8 C9 P9 111.9(2) . . ? C10 C9 P9 128.0(2) . . ? C5 C10 C9 116.4(2) . . ? C5 C10 C1 116.9(2) . . ? C9 C10 C1 126.7(3) . . ? C12 P3 C24 108.27(13) . . ? C12 P3 C18 110.45(13) . . ? C24 P3 C18 108.33(13) . . ? C12 P3 C30 107.13(15) . . ? C24 P3 C30 110.83(14) . . ? C18 P3 C30 111.79(15) . . ? C13 C12 C17 119.4(3) . . ? C13 C12 P3 121.9(2) . . ? C17 C12 P3 118.4(2) . . ? C12 C13 C14 120.1(3) . . ? C15 C14 C13 120.6(4) . . ? C16 C15 C14 119.8(3) . . ? C15 C16 C17 120.6(4) . . ? C16 C17 C12 119.6(4) . . ? C19 C18 C23 118.7(3) . . ? C19 C18 P3 121.3(3) . . ? C23 C18 P3 120.0(3) . . ? C18 C19 C20 120.0(4) . . ? C21 C20 C19 121.4(4) . . ? C20 C21 C22 119.6(4) . . ? C21 C22 C23 119.8(4) . . ? C18 C23 C22 120.5(4) . . ? C25 C24 C29 119.7(3) . . ? C25 C24 P3 119.8(2) . . ? C29 C24 P3 120.5(2) . . ? C26 C25 C24 119.4(3) . . ? C27 C26 C25 120.7(3) . . ? C26 C27 C28 119.8(3) . . ? C29 C28 C27 120.4(3) . . ? C28 C29 C24 119.9(3) . . ? C35 C30 C31_a 116.9(4) . . ? C35 C30 C31_b 109.8(4) . . ? C35 C30 P3 124.8(3) . . ? C31_a C30 P3 114.5(3) . . ? C31_b C30 P3 118.1(4) . . ? C32_a C31_a C30 118.3(5) . . ? C31_a C32_a C33 118.1(6) . . ? C32_b C31_b C30 119.8(7) . . ? C31_b C32_b C33 116.0(8) . . ? C34 C33 C32_b 112.0(5) . . ? C34 C33 C32_a 116.3(4) . . ? C33 C34 C35 121.5(4) . . ? C30 C35 C34 121.6(4) . . ? _refine_diff_density_max 0.617 _refine_diff_density_min -0.702 _refine_diff_density_rms 0.114 #===END data_6 _audit_creation_method SHELXL _chemical_name_systematic ; 2,6-(naphthalene-1,8-diyl)-3,4-dimethyl-1,3,5,2,6- thiadiazadiphosphinine-2,6-disulfide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H12 N2 P2 S3' _chemical_formula_weight 354.37 _chemical_melting_point 218-220 _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' 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' 'P' 'P' 0.1023 0.0942 '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 P21/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 7.038(3) _cell_length_b 27.939(3) _cell_length_c 7.891(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.81(3) _cell_angle_gamma 90.00 _cell_volume 1506.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 39 _cell_measurement_theta_min 9 _cell_measurement_theta_max 16 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.85 _exptl_crystal_size_mid 0.75 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.562 _exptl_crystal_density_method ? _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.693 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2888 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.11 _reflns_number_total 2668 _reflns_number_observed 2271 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0400P)^2^+1.5000P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2668 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_obs 0.0347 _refine_ls_wR_factor_all 0.0934 _refine_ls_wR_factor_obs 0.0874 _refine_ls_goodness_of_fit_all 1.030 _refine_ls_goodness_of_fit_obs 1.053 _refine_ls_restrained_S_all 1.030 _refine_ls_restrained_S_obs 1.053 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P9 P 0.50533(10) 0.18873(2) 1.00113(9) 0.03333(18) Uani 1 d . . P1 P 0.21572(9) 0.10775(2) 0.90042(8) 0.03054(17) Uani 1 d . . S9 S 0.58382(13) 0.25204(3) 1.08331(14) 0.0612(3) Uani 1 d . . S19 S 0.21572(9) 0.17760(2) 1.00026(9) 0.03715(18) Uani 1 d . . S1 S -0.04705(11) 0.08359(3) 0.83861(11) 0.0516(2) Uani 1 d . . C9 C 0.6427(4) 0.14058(10) 1.1279(3) 0.0324(5) Uani 1 d . . C8 C 0.8265(4) 0.15387(13) 1.2173(4) 0.0462(7) Uani 1 d . . C7 C 0.9517(5) 0.12168(16) 1.3242(5) 0.0606(10) Uani 1 d . . C6 C 0.8916(5) 0.07703(14) 1.3462(4) 0.0540(8) Uani 1 d . . C5 C 0.7017(4) 0.06186(11) 1.2630(4) 0.0410(6) Uani 1 d . . C10 C 0.5729(4) 0.09345(9) 1.1473(3) 0.0308(5) Uani 1 d . . C1 C 0.3821(4) 0.07549(9) 1.0698(3) 0.0318(5) Uani 1 d . . C2 C 0.3243(5) 0.03164(11) 1.1140(4) 0.0458(7) Uani 1 d . . C3 C 0.4514(6) 0.00180(12) 1.2302(5) 0.0565(9) Uani 1 d . . C4 C 0.6358(5) 0.01616(12) 1.2989(4) 0.0529(8) Uani 1 d . . N1 N 0.3227(3) 0.11043(8) 0.7392(3) 0.0349(5) Uani 1 d . . N9 N 0.5243(3) 0.17896(8) 0.7915(3) 0.0362(5) Uani 1 d . . C12 C 0.4928(5) 0.13147(16) 0.5250(4) 0.0521(8) Uani 1 d . . C11 C 0.4414(4) 0.14030(10) 0.6962(3) 0.0343(6) Uani 1 d . . C13 C 0.6497(8) 0.21126(18) 0.7188(7) 0.0678(11) Uani 1 d . . H2 H 0.8650(49) 0.1855(12) 1.2110(43) 0.053(10) Uiso 1 d . . H3 H 1.0637(56) 0.1308(13) 1.3837(47) 0.068(11) Uiso 1 d . . H4 H 1.0044(48) 0.0458(12) 1.4195(42) 0.060(10) Uiso 1 d . . H8 H 0.2017(50) 0.0227(11) 1.0710(41) 0.049(9) Uiso 1 d . . H9 H 0.4036(58) -0.0260(14) 1.2615(51) 0.077(12) Uiso 1 d . . H10 H 0.7241(54) -0.0039(13) 1.3813(47) 0.069(11) Uiso 1 d . . H20A H 0.6296(61) 0.1289(14) 0.5472(49) 0.074(12) Uiso 1 d . . H20B H 0.4283(57) 0.1008(15) 0.4759(50) 0.073(12) Uiso 1 d . . H20C H 0.4554(59) 0.1557(15) 0.4550(53) 0.074(13) Uiso 1 d . . H21A H 0.6775(60) 0.2382(15) 0.8006(56) 0.080(13) Uiso 1 d . . H21B H 0.7550(95) 0.1979(20) 0.7331(80) 0.130(24) Uiso 1 d . . H21C H 0.5915(70) 0.2203(17) 0.6068(69) 0.104(17) 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 P9 0.0302(3) 0.0300(3) 0.0420(4) -0.0033(3) 0.0132(3) -0.0009(3) P1 0.0271(3) 0.0343(4) 0.0304(3) 0.0002(3) 0.0071(3) -0.0015(3) S9 0.0554(5) 0.0375(4) 0.0933(7) -0.0207(4) 0.0231(5) -0.0101(4) S19 0.0304(3) 0.0365(4) 0.0485(4) -0.0030(3) 0.0172(3) 0.0044(3) S1 0.0312(4) 0.0635(5) 0.0570(5) 0.0018(4) 0.0042(3) -0.0130(3) C9 0.0281(12) 0.0417(14) 0.0292(13) -0.0023(11) 0.0106(10) 0.0025(11) C8 0.0319(14) 0.061(2) 0.0453(17) -0.0023(15) 0.0089(12) -0.0061(14) C7 0.0283(15) 0.095(3) 0.0524(19) 0.0044(19) -0.0022(14) -0.0018(17) C6 0.0397(16) 0.077(2) 0.0425(17) 0.0077(16) 0.0040(13) 0.0155(16) C5 0.0409(15) 0.0509(17) 0.0316(14) 0.0027(12) 0.0098(12) 0.0117(13) C10 0.0301(12) 0.0402(14) 0.0241(12) -0.0007(10) 0.0102(10) 0.0063(11) C1 0.0355(13) 0.0327(13) 0.0281(12) -0.0018(10) 0.0094(10) 0.0022(11) C2 0.0492(18) 0.0395(16) 0.0479(17) 0.0016(13) 0.0104(14) -0.0058(14) C3 0.070(2) 0.0391(17) 0.061(2) 0.0134(15) 0.0151(18) 0.0035(16) C4 0.062(2) 0.0487(18) 0.0462(17) 0.0138(15) 0.0101(15) 0.0200(16) N1 0.0359(12) 0.0388(12) 0.0310(11) -0.0010(9) 0.0100(9) 0.0029(10) N9 0.0347(12) 0.0394(12) 0.0382(12) 0.0088(10) 0.0162(10) 0.0001(10) C12 0.0430(18) 0.081(3) 0.0370(17) 0.0040(17) 0.0184(14) 0.0077(18) C11 0.0287(12) 0.0438(15) 0.0306(13) 0.0052(11) 0.0072(10) 0.0096(11) C13 0.072(3) 0.073(3) 0.069(3) 0.010(2) 0.037(2) -0.028(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 P9 N9 1.7126(23) . ? P9 C9 1.8118(27) . ? P9 S9 1.9194(10) . ? P9 S19 2.0602(13) . ? P1 N1 1.6269(22) . ? P1 C1 1.7953(26) . ? P1 S1 1.9191(12) . ? P1 S19 2.1046(10) . ? C9 C8 1.3688(39) . ? C9 C10 1.4264(37) . ? C8 C7 1.3936(48) . ? C7 C6 1.3420(53) . ? C6 C5 1.4065(45) . ? C5 C4 1.4098(45) . ? C5 C10 1.4279(36) . ? C10 C1 1.4271(37) . ? C1 C2 1.3624(38) . ? C2 C3 1.3946(46) . ? C3 C4 1.3429(51) . ? N1 C11 1.2829(34) . ? N9 C11 1.3648(35) . ? N9 C13 1.4716(39) . ? C12 C11 1.5004(39) . ? 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 N9 P9 C9 105.10(11) . . ? N9 P9 S9 113.00(9) . . ? C9 P9 S9 115.16(10) . . ? N9 P9 S19 106.12(9) . . ? C9 P9 S19 106.67(9) . . ? S9 P9 S19 110.18(5) . . ? N1 P1 C1 105.29(12) . . ? N1 P1 S1 114.52(9) . . ? C1 P1 S1 115.50(9) . . ? N1 P1 S19 106.94(9) . . ? C1 P1 S19 104.19(9) . . ? S1 P1 S19 109.58(5) . . ? P9 S19 P1 93.03(4) . . ? C8 C9 C10 120.2(3) . . ? C8 C9 P9 113.4(2) . . ? C10 C9 P9 126.34(19) . . ? C9 C8 C7 121.3(3) . . ? C6 C7 C8 120.3(3) . . ? C7 C6 C5 120.9(3) . . ? C6 C5 C4 120.0(3) . . ? C6 C5 C10 120.0(3) . . ? C4 C5 C10 120.0(3) . . ? C9 C10 C1 126.3(2) . . ? C9 C10 C5 117.2(2) . . ? C1 C10 C5 116.4(2) . . ? C2 C1 C10 121.0(3) . . ? C2 C1 P1 117.4(2) . . ? C10 C1 P1 121.50(19) . . ? C1 C2 C3 121.5(3) . . ? C4 C3 C2 119.5(3) . . ? C3 C4 C5 121.5(3) . . ? C11 N1 P1 133.5(2) . . ? C11 N9 C13 119.2(3) . . ? C11 N9 P9 122.47(18) . . ? C13 N9 P9 118.1(3) . . ? N1 C11 N9 126.1(2) . . ? N1 C11 C12 116.3(3) . . ? N9 C11 C12 117.6(3) . . ? _refine_diff_density_max 0.350 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.060