# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Maria Babashkina' _publ_contact_author_email maria.babashkina@ksu.ru _publ_section_title ; N-(Diisopropylthiophosphoryl)-N'-(R)-thioureas: synthesis, characterization and crystal structures. Competitive bulk liquid membrane transport and solvent extraction of some metal ions ; _publ_author_name M.Babashkina data_1 _database_code_depnum_ccdc_archive 'CCDC 805546' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C10 H23 N2 O2 P S2' _chemical_formula_sum 'C10 H23 N2 O2 P S2' _chemical_formula_weight 298.39 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' 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7411(4) _cell_length_b 9.4953(4) _cell_length_c 10.2409(5) _cell_angle_alpha 94.511(2) _cell_angle_beta 99.974(2) _cell_angle_gamma 94.849(2) _cell_volume 830.37(7) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 0.411 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7730 _exptl_absorpt_correction_T_max 0.9113 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 21707 _diffrn_reflns_av_R_equivalents 0.0171 _diffrn_reflns_av_sigmaI/netI 0.0152 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 32.61 _reflns_number_total 6020 _reflns_number_gt 5350 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0421P)^2^+0.1715P] 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 6020 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0770 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 S1 S 0.69149(3) 0.68056(3) 1.09444(2) 0.03233(6) Uani 1 1 d . . . P1 P 0.72300(2) 0.68517(2) 0.91459(2) 0.02238(5) Uani 1 1 d . . . O1 O 0.79311(7) 0.55637(7) 0.84786(7) 0.02753(12) Uani 1 1 d . . . N1 N 0.85280(9) 0.81957(8) 0.89977(7) 0.02533(14) Uani 1 1 d . . . H1 H 0.8923(16) 0.8673(15) 0.9710(14) 0.039(3) Uiso 1 1 d . . . S2 S 1.01921(3) 1.01436(2) 0.79780(2) 0.03346(6) Uani 1 1 d . . . O2 O 0.57316(7) 0.69434(7) 0.80520(6) 0.02634(12) Uani 1 1 d . . . N2 N 0.84978(12) 0.78219(10) 0.67373(8) 0.0367(2) Uani 1 1 d . . . H2 H 0.7955(19) 0.7126(17) 0.6786(15) 0.052(4) Uiso 1 1 d . . . C1 C 0.90031(10) 0.86429(9) 0.78691(8) 0.02353(14) Uani 1 1 d . . . C8 C 0.87249(13) 0.81737(11) 0.54104(9) 0.0350(2) Uani 1 1 d . . . H8 H 0.9740 0.8777 0.5508 0.042 Uiso 1 1 calc R . . C9 C 0.74404(17) 0.90044(19) 0.47962(13) 0.0569(4) Uani 1 1 d . . . H9A H 0.7429 0.9877 0.5372 0.085 Uiso 1 1 calc R . . H9B H 0.6434 0.8430 0.4698 0.085 Uiso 1 1 calc R . . H9C H 0.7620 0.9247 0.3919 0.085 Uiso 1 1 calc R . . C10 C 0.8831(2) 0.68081(16) 0.45803(13) 0.0634(4) Uani 1 1 d . . . H10A H 0.9685 0.6314 0.5025 0.095 Uiso 1 1 calc R . . H10B H 0.9031 0.7025 0.3702 0.095 Uiso 1 1 calc R . . H10C H 0.7845 0.6201 0.4476 0.095 Uiso 1 1 calc R . . C2 C 0.71886(11) 0.41028(10) 0.84425(12) 0.0344(2) Uani 1 1 d . . . H2A H 0.6217 0.4121 0.8833 0.041 Uiso 1 1 calc R . . C3 C 0.83417(15) 0.32988(12) 0.92730(15) 0.0488(3) Uani 1 1 d . . . H3A H 0.8550 0.3728 1.0196 0.073 Uiso 1 1 calc R . . H3B H 0.9317 0.3336 0.8921 0.073 Uiso 1 1 calc R . . H3C H 0.7911 0.2307 0.9243 0.073 Uiso 1 1 calc R . . C4 C 0.6780(2) 0.35236(18) 0.70055(17) 0.0735(5) Uani 1 1 d . . . H4A H 0.6028 0.4096 0.6525 0.110 Uiso 1 1 calc R . . H4B H 0.6318 0.2538 0.6942 0.110 Uiso 1 1 calc R . . H4C H 0.7726 0.3559 0.6612 0.110 Uiso 1 1 calc R . . C5 C 0.44616(11) 0.78002(11) 0.82712(10) 0.03339(19) Uani 1 1 d . . . H5 H 0.4245 0.7703 0.9189 0.040 Uiso 1 1 calc R . . C6 C 0.30553(14) 0.71629(17) 0.72667(15) 0.0559(3) Uani 1 1 d . . . H6A H 0.2814 0.6168 0.7414 0.084 Uiso 1 1 calc R . . H6B H 0.3279 0.7216 0.6366 0.084 Uiso 1 1 calc R . . H6C H 0.2160 0.7691 0.7368 0.084 Uiso 1 1 calc R . . C7 C 0.49333(17) 0.93418(13) 0.81390(17) 0.0547(3) Uani 1 1 d . . . H7A H 0.5851 0.9683 0.8818 0.082 Uiso 1 1 calc R . . H7B H 0.4070 0.9904 0.8261 0.082 Uiso 1 1 calc R . . H7C H 0.5184 0.9439 0.7252 0.082 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.03115(11) 0.04101(13) 0.02409(10) 0.00684(8) 0.00553(8) -0.00524(9) P1 0.02101(9) 0.02322(10) 0.02212(10) 0.00349(7) 0.00232(7) -0.00042(7) O1 0.0241(3) 0.0227(3) 0.0364(3) 0.0041(2) 0.0073(2) 0.0010(2) N1 0.0292(3) 0.0252(3) 0.0195(3) 0.0018(2) 0.0028(2) -0.0055(3) S2 0.04404(13) 0.02856(11) 0.02668(11) -0.00282(8) 0.01332(9) -0.01208(9) O2 0.0230(3) 0.0289(3) 0.0254(3) 0.0000(2) 0.0001(2) 0.0041(2) N2 0.0519(5) 0.0333(4) 0.0204(3) 0.0008(3) 0.0049(3) -0.0171(4) C1 0.0256(3) 0.0226(3) 0.0216(3) 0.0019(3) 0.0034(3) 0.0000(3) C8 0.0424(5) 0.0403(5) 0.0205(4) 0.0033(3) 0.0055(3) -0.0070(4) C9 0.0500(7) 0.0865(10) 0.0390(6) 0.0237(6) 0.0104(5) 0.0140(7) C10 0.1060(13) 0.0530(8) 0.0294(5) -0.0055(5) 0.0150(7) 0.0000(8) C2 0.0271(4) 0.0236(4) 0.0517(6) 0.0013(4) 0.0080(4) -0.0024(3) C3 0.0460(6) 0.0313(5) 0.0737(9) 0.0170(5) 0.0152(6) 0.0105(4) C4 0.0873(12) 0.0539(8) 0.0634(9) -0.0171(7) -0.0095(9) -0.0158(8) C5 0.0278(4) 0.0387(5) 0.0337(4) 0.0014(4) 0.0028(3) 0.0113(3) C6 0.0304(5) 0.0663(8) 0.0636(8) -0.0075(7) -0.0101(5) 0.0133(5) C7 0.0550(7) 0.0362(6) 0.0735(9) 0.0045(6) 0.0071(6) 0.0175(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 P1 1.9122(3) . ? P1 O1 1.5743(7) . ? P1 O2 1.5825(6) . ? P1 N1 1.6685(7) . ? O1 C2 1.4759(11) . ? N1 C1 1.3792(11) . ? N1 H1 0.831(15) . ? S2 C1 1.6757(8) . ? O2 C5 1.4680(11) . ? N2 C1 1.3298(11) . ? N2 C8 1.4666(12) . ? N2 H2 0.790(16) . ? C8 C9 1.5039(18) . ? C8 C10 1.5122(17) . ? C8 H8 1.0000 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C2 C4 1.5010(19) . ? C2 C3 1.5025(16) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.5079(16) . ? C5 C7 1.5098(17) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? 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 O1 P1 O2 99.77(4) . . ? O1 P1 N1 101.11(4) . . ? O2 P1 N1 107.02(4) . . ? O1 P1 S1 118.87(3) . . ? O2 P1 S1 116.73(3) . . ? N1 P1 S1 111.48(3) . . ? C2 O1 P1 120.46(6) . . ? C1 N1 P1 129.44(6) . . ? C1 N1 H1 115.9(10) . . ? P1 N1 H1 114.6(10) . . ? C5 O2 P1 123.35(6) . . ? C1 N2 C8 125.61(8) . . ? C1 N2 H2 116.1(11) . . ? C8 N2 H2 117.9(11) . . ? N2 C1 N1 116.95(8) . . ? N2 C1 S2 123.30(7) . . ? N1 C1 S2 119.74(6) . . ? N2 C8 C9 110.49(10) . . ? N2 C8 C10 108.25(9) . . ? C9 C8 C10 112.98(11) . . ? N2 C8 H8 108.3 . . ? C9 C8 H8 108.3 . . ? C10 C8 H8 108.3 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C2 C4 106.99(10) . . ? O1 C2 C3 106.84(8) . . ? C4 C2 C3 113.81(12) . . ? O1 C2 H2A 109.7 . . ? C4 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C6 105.61(9) . . ? O2 C5 C7 109.85(9) . . ? C6 C5 C7 113.93(11) . . ? O2 C5 H5 109.1 . . ? C6 C5 H5 109.1 . . ? C7 C5 H5 109.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C2 -73.41(7) . . . . ? N1 P1 O1 C2 176.93(7) . . . . ? S1 P1 O1 C2 54.62(7) . . . . ? O1 P1 N1 C1 57.04(9) . . . . ? O2 P1 N1 C1 -46.90(9) . . . . ? S1 P1 N1 C1 -175.66(7) . . . . ? O1 P1 O2 C5 167.86(7) . . . . ? N1 P1 O2 C5 -87.24(8) . . . . ? S1 P1 O2 C5 38.43(8) . . . . ? C8 N2 C1 N1 173.10(10) . . . . ? C8 N2 C1 S2 -8.12(16) . . . . ? P1 N1 C1 N2 -7.85(13) . . . . ? P1 N1 C1 S2 173.33(5) . . . . ? C1 N2 C8 C9 -86.90(14) . . . . ? C1 N2 C8 C10 148.90(13) . . . . ? P1 O1 C2 C4 122.38(11) . . . . ? P1 O1 C2 C3 -115.38(9) . . . . ? P1 O2 C5 C6 -158.06(9) . . . . ? P1 O2 C5 C7 78.67(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S2 0.831(15) 2.504(15) 3.3262(8) 170.5(13) 2_777 N2 H2 O1 0.790(16) 2.370(16) 2.9582(11) 132.0(14) . N2 H2 O2 0.790(16) 2.518(16) 3.0526(11) 126.2(14) . _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.379 _refine_diff_density_min -0.366 _refine_diff_density_rms 0.043 # Attachment '- 8.cif' data_6 _database_code_depnum_ccdc_archive 'CCDC 818223' #TrackingRef '- 8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H22 N3 O2 P S2' _chemical_formula_sum 'C13 H22 N3 O2 P S2' _chemical_formula_weight 347.43 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.6949(8) _cell_length_b 17.153(2) _cell_length_c 13.2985(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.175(10) _cell_angle_gamma 90.00 _cell_volume 1755.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 140(2) _cell_measurement_reflns_used 5039 _cell_measurement_theta_min 2.6417 _cell_measurement_theta_max 25.4219 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.315 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 0.401 _exptl_absorpt_correction_T_min 0.82866 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 140(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'RU200 rotating anode' _diffrn_radiation_monochromator 'Zr filter' _diffrn_measurement_device_type 'MAR345 image plate' _diffrn_measurement_method '46 images, \D\F 3.0\%' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8683 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0265 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 25.48 _reflns_number_total 3210 _reflns_number_gt 2964 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics PLATON _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.9229P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.028(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3210 _refine_ls_number_parameters 195 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1073 _refine_ls_wR_factor_gt 0.1050 _refine_ls_goodness_of_fit_ref 1.159 _refine_ls_restrained_S_all 1.159 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.16920(6) 0.16559(3) 0.35237(3) 0.01570(16) Uani 1 1 d . . . S1 S 0.13324(6) 0.23601(3) 0.46253(4) 0.02219(17) Uani 1 1 d . . . O1 O 0.36178(16) 0.15526(8) 0.31444(10) 0.0200(3) Uani 1 1 d . . . C2 C 0.5139(3) 0.15640(14) 0.38104(16) 0.0293(5) Uani 1 1 d . . . H2A H 0.4801 0.1779 0.4481 0.035 Uiso 1 1 calc R . . C3 C 0.6434(3) 0.21004(16) 0.3321(2) 0.0411(6) Uani 1 1 d . . . H3A H 0.6723 0.1902 0.2651 0.062 Uiso 1 1 calc R . . H3B H 0.7491 0.2125 0.3733 0.062 Uiso 1 1 calc R . . H3C H 0.5932 0.2623 0.3261 0.062 Uiso 1 1 calc R . . C4 C 0.5775(4) 0.07403(18) 0.3935(2) 0.0515(7) Uani 1 1 d . . . H4A H 0.4857 0.0423 0.4239 0.077 Uiso 1 1 calc R . . H4B H 0.6803 0.0736 0.4372 0.077 Uiso 1 1 calc R . . H4C H 0.6078 0.0525 0.3276 0.077 Uiso 1 1 calc R . . O2 O 0.07622(17) 0.18498(7) 0.24938(10) 0.0185(3) Uani 1 1 d . . . C5 C 0.1298(3) 0.25804(11) 0.19724(14) 0.0202(4) Uani 1 1 d . . . H5 H 0.2193 0.2853 0.2390 0.024 Uiso 1 1 calc R . . C6 C -0.0288(3) 0.30919(13) 0.18847(17) 0.0304(5) Uani 1 1 d . . . H6A H -0.1182 0.2822 0.1490 0.046 Uiso 1 1 calc R . . H6B H 0.0025 0.3581 0.1549 0.046 Uiso 1 1 calc R . . H6C H -0.0738 0.3205 0.2558 0.046 Uiso 1 1 calc R . . C7 C 0.2091(3) 0.23536(12) 0.09824(15) 0.0264(5) Uani 1 1 d . . . H7A H 0.3069 0.1999 0.1101 0.040 Uiso 1 1 calc R . . H7B H 0.2507 0.2822 0.0636 0.040 Uiso 1 1 calc R . . H7C H 0.1215 0.2092 0.0565 0.040 Uiso 1 1 calc R . . N1 N 0.0943(2) 0.07641(9) 0.37854(12) 0.0187(3) Uani 1 1 d . . . H1 H 0.0378 0.0723 0.4357 0.022 Uiso 1 1 calc R . . C1 C 0.1079(2) 0.00759(11) 0.32359(14) 0.0188(4) Uani 1 1 d . . . S2 S 0.03421(7) -0.07615(3) 0.37380(4) 0.02646(17) Uani 1 1 d . . . N2 N 0.1784(2) 0.01221(9) 0.23292(12) 0.0225(4) Uani 1 1 d . . . H2 H 0.2160 0.0579 0.2123 0.027 Uiso 1 1 calc R . . C8 C 0.1971(3) -0.05431(11) 0.16542(15) 0.0248(4) Uani 1 1 d . . . H8A H 0.0917 -0.0873 0.1688 0.030 Uiso 1 1 calc R . . H8B H 0.2979 -0.0863 0.1866 0.030 Uiso 1 1 calc R . . C9 C 0.2233(2) -0.02618(11) 0.05887(15) 0.0200(4) Uani 1 1 d . . . N3 N 0.2915(2) 0.04496(10) 0.04753(13) 0.0242(4) Uani 1 1 d . . . C13 C 0.3159(3) 0.07027(12) -0.04683(16) 0.0280(5) Uani 1 1 d . . . H13 H 0.3645 0.1207 -0.0561 0.034 Uiso 1 1 calc R . . C12 C 0.2742(3) 0.02700(13) -0.13149(16) 0.0302(5) Uani 1 1 d . . . H12 H 0.2928 0.0474 -0.1970 0.036 Uiso 1 1 calc R . . C11 C 0.2048(3) -0.04654(12) -0.11829(16) 0.0278(5) Uani 1 1 d . . . H11 H 0.1751 -0.0779 -0.1747 0.033 Uiso 1 1 calc R . . C10 C 0.1794(3) -0.07382(11) -0.02175(16) 0.0227(4) Uani 1 1 d . . . H10 H 0.1326 -0.1243 -0.0107 0.027 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0157(3) 0.0173(3) 0.0141(3) -0.00044(17) 0.00064(18) -0.00180(16) S1 0.0239(3) 0.0234(3) 0.0194(3) -0.00584(18) 0.00285(19) -0.00076(18) O1 0.0168(6) 0.0271(7) 0.0160(7) -0.0020(5) 0.0012(5) -0.0018(5) C2 0.0161(9) 0.0514(14) 0.0205(10) -0.0049(9) -0.0019(8) 0.0016(9) C3 0.0233(11) 0.0535(15) 0.0464(15) -0.0111(12) 0.0045(10) -0.0103(10) C4 0.0396(14) 0.0636(19) 0.0513(17) 0.0232(14) -0.0023(12) 0.0128(12) O2 0.0213(7) 0.0162(6) 0.0180(7) 0.0019(5) -0.0023(5) -0.0045(5) C5 0.0268(10) 0.0149(9) 0.0188(9) 0.0016(7) -0.0015(8) -0.0052(7) C6 0.0363(12) 0.0248(11) 0.0300(11) 0.0053(9) 0.0010(9) 0.0056(9) C7 0.0353(11) 0.0220(10) 0.0221(10) 0.0010(8) 0.0047(9) -0.0049(8) N1 0.0235(8) 0.0182(8) 0.0146(8) 0.0012(6) 0.0043(6) -0.0017(6) C1 0.0203(9) 0.0185(9) 0.0177(9) 0.0029(7) -0.0012(7) 0.0011(7) S2 0.0415(3) 0.0173(3) 0.0206(3) 0.00382(18) 0.0064(2) -0.0031(2) N2 0.0331(9) 0.0148(8) 0.0196(9) 0.0004(6) 0.0045(7) -0.0023(6) C8 0.0383(11) 0.0169(9) 0.0191(10) -0.0007(8) 0.0040(8) 0.0019(8) C9 0.0202(9) 0.0175(9) 0.0224(10) -0.0003(7) 0.0027(7) 0.0035(7) N3 0.0326(9) 0.0209(8) 0.0192(9) -0.0005(7) 0.0033(7) -0.0020(7) C13 0.0400(12) 0.0196(10) 0.0243(11) -0.0002(8) 0.0081(9) -0.0034(8) C12 0.0407(12) 0.0320(11) 0.0180(10) 0.0007(8) 0.0066(9) 0.0028(9) C11 0.0322(11) 0.0283(11) 0.0229(10) -0.0077(8) -0.0015(8) 0.0024(9) C10 0.0238(10) 0.0179(9) 0.0266(11) -0.0025(8) 0.0006(8) 0.0014(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 P1 O1 1.5768(14) . ? P1 O2 1.5786(13) . ? P1 N1 1.6716(16) . ? P1 S1 1.9194(7) . ? O1 C2 1.466(2) . ? C2 C4 1.504(4) . ? C2 C3 1.506(3) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? O2 C5 1.491(2) . ? C5 C7 1.504(3) . ? C5 C6 1.507(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? N1 C1 1.392(3) . ? N1 H1 0.8800 . ? C1 N2 1.326(3) . ? C1 S2 1.6830(19) . ? N2 C8 1.459(2) . ? N2 H2 0.8800 . ? C8 C9 1.511(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N3 1.337(3) . ? C9 C10 1.389(3) . ? N3 C13 1.341(3) . ? C13 C12 1.385(3) . ? C13 H13 0.9500 . ? C12 C11 1.381(3) . ? C12 H12 0.9500 . ? C11 C10 1.381(3) . ? C11 H11 0.9500 . ? C10 H10 0.9500 . ? 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 O1 P1 O2 99.79(7) . . ? O1 P1 N1 106.77(8) . . ? O2 P1 N1 102.58(7) . . ? O1 P1 S1 116.92(6) . . ? O2 P1 S1 117.62(6) . . ? N1 P1 S1 111.49(6) . . ? C2 O1 P1 123.70(12) . . ? O1 C2 C4 108.23(19) . . ? O1 C2 C3 105.99(18) . . ? C4 C2 C3 114.0(2) . . ? O1 C2 H2A 109.5 . . ? C4 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C5 O2 P1 117.09(11) . . ? O2 C5 C7 107.65(15) . . ? O2 C5 C6 107.49(16) . . ? C7 C5 C6 114.43(17) . . ? O2 C5 H5 109.1 . . ? C7 C5 H5 109.1 . . ? C6 C5 H5 109.1 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C1 N1 P1 129.81(14) . . ? C1 N1 H1 115.1 . . ? P1 N1 H1 115.1 . . ? N2 C1 N1 117.26(16) . . ? N2 C1 S2 123.43(15) . . ? N1 C1 S2 119.31(15) . . ? C1 N2 C8 123.65(17) . . ? C1 N2 H2 118.2 . . ? C8 N2 H2 118.2 . . ? N2 C8 C9 109.93(16) . . ? N2 C8 H8A 109.7 . . ? C9 C8 H8A 109.7 . . ? N2 C8 H8B 109.7 . . ? C9 C8 H8B 109.7 . . ? H8A C8 H8B 108.2 . . ? N3 C9 C10 123.00(18) . . ? N3 C9 C8 116.80(17) . . ? C10 C9 C8 120.20(18) . . ? C9 N3 C13 117.18(17) . . ? N3 C13 C12 123.65(19) . . ? N3 C13 H13 118.2 . . ? C12 C13 H13 118.2 . . ? C11 C12 C13 118.3(2) . . ? C11 C12 H12 120.8 . . ? C13 C12 H12 120.8 . . ? C10 C11 C12 118.91(19) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C11 C10 C9 118.91(19) . . ? C11 C10 H10 120.5 . . ? C9 C10 H10 120.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C2 163.47(15) . . . . ? N1 P1 O1 C2 -90.10(16) . . . . ? S1 P1 O1 C2 35.51(17) . . . . ? P1 O1 C2 C4 104.82(19) . . . . ? P1 O1 C2 C3 -132.53(16) . . . . ? O1 P1 O2 C5 -63.38(14) . . . . ? N1 P1 O2 C5 -173.16(13) . . . . ? S1 P1 O2 C5 64.12(13) . . . . ? P1 O2 C5 C7 116.82(15) . . . . ? P1 O2 C5 C6 -119.46(15) . . . . ? O1 P1 N1 C1 -45.03(18) . . . . ? O2 P1 N1 C1 59.40(18) . . . . ? S1 P1 N1 C1 -173.85(15) . . . . ? P1 N1 C1 N2 -5.8(3) . . . . ? P1 N1 C1 S2 174.62(10) . . . . ? N1 C1 N2 C8 -178.27(17) . . . . ? S2 C1 N2 C8 1.3(3) . . . . ? C1 N2 C8 C9 160.81(18) . . . . ? N2 C8 C9 N3 25.3(2) . . . . ? N2 C8 C9 C10 -155.47(18) . . . . ? C10 C9 N3 C13 0.6(3) . . . . ? C8 C9 N3 C13 179.74(18) . . . . ? C9 N3 C13 C12 0.1(3) . . . . ? N3 C13 C12 C11 -0.5(3) . . . . ? C13 C12 C11 C10 0.2(3) . . . . ? C12 C11 C10 C9 0.4(3) . . . . ? N3 C9 C10 C11 -0.8(3) . . . . ? C8 C9 C10 C11 179.99(18) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.523 _refine_diff_density_min -0.527 _refine_diff_density_rms 0.170 # Attachment '- 4.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 818224' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H25 N2 O2 P S2' _chemical_formula_sum 'C15 H25 N2 O2 P S2' _chemical_formula_weight 360.46 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' 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/c _symmetry_space_group_name_Hall '-P 2ybc' 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 9.6981(5) _cell_length_b 16.1422(10) _cell_length_c 13.1345(6) _cell_angle_alpha 90.00 _cell_angle_beta 111.037(3) _cell_angle_gamma 90.00 _cell_volume 1919.14(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.368 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9267 _exptl_absorpt_correction_T_max 0.9606 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 31989 _diffrn_reflns_av_R_equivalents 0.0974 _diffrn_reflns_av_sigmaI/netI 0.0529 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.68 _reflns_number_total 3640 _reflns_number_gt 2369 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material SHELXL97 _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^)+(0.0481P)^2^+1.9187P] 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 3640 _refine_ls_number_parameters 202 _refine_ls_number_restraints 20 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_ref 0.1351 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.65038(12) 0.55254(6) 0.78718(7) 0.0423(3) Uani 1 1 d . . . S1 S 0.61273(13) 0.64081(6) 0.86978(9) 0.0576(3) Uani 1 1 d . A . S2 S 1.04690(10) 0.40984(6) 0.90116(7) 0.0470(3) Uani 1 1 d . A . N1 N 0.8153(3) 0.50997(19) 0.8507(2) 0.0444(7) Uani 1 1 d D A . H1 H 0.867(3) 0.525(2) 0.9177(13) 0.048(11) Uiso 1 1 d D . . N2 N 0.8039(4) 0.4074(2) 0.7271(2) 0.0487(8) Uani 1 1 d D A . H2 H 0.718(3) 0.430(2) 0.689(3) 0.078(15) Uiso 1 1 d D . . O2 O 0.6906(8) 0.5751(3) 0.6851(4) 0.0334(17) Uiso 0.495(12) 1 d PD A 1 O2' O 0.6165(8) 0.5681(3) 0.6585(4) 0.0346(17) Uiso 0.505(12) 1 d PD A 2 C1 C 0.8807(4) 0.4432(2) 0.8223(3) 0.0387(8) Uani 1 1 d . . . O1 O 0.5381(2) 0.47853(14) 0.75454(18) 0.0400(6) Uani 1 1 d D A . C2 C 0.4729(4) 0.4416(2) 0.8289(3) 0.0524(10) Uani 1 1 d D . . H2A H 0.4360 0.4868 0.8645 0.063 Uiso 1 1 calc R A . C3 C 0.3444(5) 0.3919(3) 0.7576(5) 0.0887(17) Uani 1 1 d D A . H3A H 0.2752 0.4284 0.7034 0.133 Uiso 1 1 calc R . . H3B H 0.2943 0.3661 0.8024 0.133 Uiso 1 1 calc R . . H3C H 0.3795 0.3488 0.7203 0.133 Uiso 1 1 calc R . . C4 C 0.5858(6) 0.3918(4) 0.9152(4) 0.0908(18) Uani 1 1 d D A . H4A H 0.6657 0.4283 0.9593 0.136 Uiso 1 1 calc R . . H4B H 0.6262 0.3491 0.8808 0.136 Uiso 1 1 calc R . . H4C H 0.5395 0.3654 0.9621 0.136 Uiso 1 1 calc R . . C5 C 0.6303(4) 0.6497(2) 0.6171(3) 0.0441(9) Uiso 1 1 d D . . H5 H 0.6120 0.6893 0.6694 0.053 Uiso 0.495(12) 1 calc PR A 1 H5' H 0.6260 0.6961 0.6662 0.053 Uiso 0.505(12) 1 calc PR A 2 C6 C 0.4821(13) 0.6321(11) 0.5390(14) 0.140(7) Uiso 0.495(12) 1 d PD A 1 H6A H 0.4207 0.6101 0.5779 0.210 Uiso 0.495(12) 1 calc PR A 1 H6B H 0.4885 0.5912 0.4858 0.210 Uiso 0.495(12) 1 calc PR A 1 H6C H 0.4379 0.6832 0.5011 0.210 Uiso 0.495(12) 1 calc PR A 1 C7 C 0.7539(12) 0.6850(9) 0.5979(11) 0.086(4) Uiso 0.495(12) 1 d PD A 1 H7A H 0.8361 0.6919 0.6675 0.129 Uiso 0.495(12) 1 calc PR A 1 H7B H 0.7261 0.7391 0.5625 0.129 Uiso 0.495(12) 1 calc PR A 1 H7C H 0.7842 0.6482 0.5504 0.129 Uiso 0.495(12) 1 calc PR A 1 C6' C 0.5078(11) 0.6521(7) 0.5042(8) 0.075(3) Uiso 0.505(12) 1 d PD A 2 H6'1 H 0.4113 0.6506 0.5124 0.112 Uiso 0.505(12) 1 calc PR A 2 H6'2 H 0.5174 0.6041 0.4616 0.112 Uiso 0.505(12) 1 calc PR A 2 H6'3 H 0.5164 0.7031 0.4665 0.112 Uiso 0.505(12) 1 calc PR A 2 C7' C 0.7638(12) 0.6529(9) 0.5818(11) 0.091(4) Uiso 0.505(12) 1 d PD A 2 H7'1 H 0.8547 0.6521 0.6464 0.137 Uiso 0.505(12) 1 calc PR A 2 H7'2 H 0.7603 0.7039 0.5404 0.137 Uiso 0.505(12) 1 calc PR A 2 H7'3 H 0.7623 0.6049 0.5358 0.137 Uiso 0.505(12) 1 calc PR A 2 C8 C 0.8481(4) 0.3325(2) 0.6887(3) 0.0382(8) Uani 1 1 d . . . C9 C 0.9101(4) 0.3372(2) 0.6084(3) 0.0414(8) Uani 1 1 d . A . C10 C 0.9446(4) 0.2623(2) 0.5719(3) 0.0490(9) Uani 1 1 d . . . H10 H 0.9869 0.2626 0.5169 0.059 Uiso 1 1 calc R A . C11 C 0.9200(4) 0.1879(2) 0.6121(3) 0.0498(10) Uani 1 1 d . A . H11 H 0.9459 0.1381 0.5850 0.060 Uiso 1 1 calc R . . C12 C 0.8578(4) 0.1841(2) 0.6919(3) 0.0462(9) Uani 1 1 d . . . C13 C 0.8219(4) 0.2585(2) 0.7287(3) 0.0447(9) Uani 1 1 d . A . H13 H 0.7782 0.2580 0.7829 0.054 Uiso 1 1 calc R . . C14 C 0.9350(5) 0.4187(3) 0.5633(4) 0.0636(11) Uani 1 1 d . . . H14A H 0.8395 0.4438 0.5212 0.095 Uiso 1 1 calc R A . H14B H 0.9918 0.4100 0.5158 0.095 Uiso 1 1 calc R . . H14C H 0.9899 0.4556 0.6235 0.095 Uiso 1 1 calc R . . C15 C 0.8304(5) 0.1031(3) 0.7378(4) 0.0734(13) Uani 1 1 d . A . H15A H 0.9037 0.0955 0.8114 0.110 Uiso 1 1 calc R . . H15B H 0.8386 0.0576 0.6909 0.110 Uiso 1 1 calc R . . H15C H 0.7311 0.1033 0.7412 0.110 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0645(6) 0.0311(5) 0.0399(5) -0.0045(4) 0.0290(5) 0.0008(5) S1 0.0747(7) 0.0460(6) 0.0620(7) -0.0195(5) 0.0365(6) 0.0032(5) S2 0.0389(5) 0.0601(6) 0.0445(5) -0.0259(5) 0.0181(4) -0.0083(5) N1 0.0440(18) 0.0472(18) 0.0461(18) -0.0244(15) 0.0211(15) -0.0052(15) N2 0.0483(19) 0.0485(19) 0.0420(18) -0.0209(15) 0.0074(15) 0.0090(16) C1 0.0415(19) 0.043(2) 0.0394(19) -0.0152(16) 0.0239(16) -0.0141(16) O1 0.0425(14) 0.0380(13) 0.0370(13) -0.0026(10) 0.0113(11) 0.0032(11) C2 0.049(2) 0.054(2) 0.066(3) -0.001(2) 0.036(2) -0.0002(19) C3 0.063(3) 0.084(4) 0.135(5) -0.044(3) 0.054(3) -0.027(3) C4 0.092(4) 0.112(4) 0.090(4) 0.055(3) 0.058(3) 0.027(3) C8 0.0359(18) 0.040(2) 0.0342(18) -0.0152(15) 0.0073(15) 0.0019(16) C9 0.0380(19) 0.043(2) 0.0403(19) -0.0120(16) 0.0100(16) -0.0026(16) C10 0.055(2) 0.050(2) 0.050(2) -0.0139(18) 0.0282(19) -0.0006(19) C11 0.051(2) 0.045(2) 0.050(2) -0.0165(18) 0.0133(19) 0.0078(18) C12 0.047(2) 0.037(2) 0.045(2) -0.0058(16) 0.0045(17) -0.0030(17) C13 0.048(2) 0.052(2) 0.0342(19) -0.0093(17) 0.0144(16) -0.0047(18) C14 0.071(3) 0.053(3) 0.074(3) -0.006(2) 0.034(2) -0.012(2) C15 0.086(3) 0.050(3) 0.069(3) 0.006(2) 0.010(3) -0.004(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 O2 1.568(4) . ? P1 O1 1.569(2) . ? P1 O2' 1.621(5) . ? P1 N1 1.664(3) . ? P1 S1 1.9039(12) . ? S2 C1 1.662(4) . ? N1 C1 1.369(4) . ? N1 H1 0.875(10) . ? N2 C1 1.336(4) . ? N2 C8 1.434(4) . ? N2 H2 0.88(3) . ? O2 C5 1.488(6) . ? O2' C5 1.449(5) . ? O1 C2 1.467(4) . ? C2 C4 1.496(6) . ? C2 C3 1.495(5) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.429(9) . ? C5 C6 1.463(11) . ? C5 C7' 1.525(10) . ? C5 C6' 1.532(9) . ? C5 H5 1.0000 . ? C5 H5' 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C6' H6'1 0.9800 . ? C6' H6'2 0.9800 . ? C6' H6'3 0.9800 . ? C7' H7'1 0.9800 . ? C7' H7'2 0.9800 . ? C7' H7'3 0.9800 . ? C8 C13 1.366(5) . ? C8 C9 1.391(5) . ? C9 C10 1.386(5) . ? C9 C14 1.497(5) . ? C10 C11 1.367(5) . ? C10 H10 0.9500 . ? C11 C12 1.385(5) . ? C11 H11 0.9500 . ? C12 C13 1.384(5) . ? C12 C15 1.504(5) . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 P1 O1 107.7(3) . . ? O1 P1 O2' 88.4(2) . . ? O2 P1 N1 92.0(3) . . ? O1 P1 N1 105.70(14) . . ? O2' P1 N1 112.7(3) . . ? O2 P1 S1 118.13(17) . . ? O1 P1 S1 117.99(10) . . ? O2' P1 S1 117.99(17) . . ? N1 P1 S1 111.71(11) . . ? C1 N1 P1 130.2(2) . . ? C1 N1 H1 109(2) . . ? P1 N1 H1 120(2) . . ? C1 N2 C8 123.9(3) . . ? C1 N2 H2 117(3) . . ? C8 N2 H2 119(3) . . ? C5 O2 P1 122.4(4) . . ? C5 O2' P1 121.4(4) . . ? N2 C1 N1 116.0(3) . . ? N2 C1 S2 122.3(3) . . ? N1 C1 S2 121.7(3) . . ? C2 O1 P1 123.4(2) . . ? O1 C2 C4 110.5(3) . . ? O1 C2 C3 105.2(3) . . ? C4 C2 C3 113.9(4) . . ? O1 C2 H2A 109.0 . . ? C4 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C7 C5 O2' 128.7(6) . . ? C7 C5 C6 129.0(10) . . ? O2' C5 C6 83.5(7) . . ? C7 C5 O2 104.8(6) . . ? C6 C5 O2 109.8(7) . . ? O2' C5 C7' 110.4(6) . . ? C6 C5 C7' 121.5(10) . . ? O2 C5 C7' 91.0(6) . . ? C7 C5 C6' 103.1(7) . . ? O2' C5 C6' 104.0(5) . . ? O2 C5 C6' 127.1(5) . . ? C7' C5 C6' 98.8(7) . . ? C7 C5 H5 103.5 . . ? O2' C5 H5 105.0 . . ? C6 C5 H5 103.5 . . ? O2 C5 H5 103.5 . . ? C7' C5 H5 124.5 . . ? C6' C5 H5 112.4 . . ? C7 C5 H5' 92.7 . . ? O2' C5 H5' 114.0 . . ? C6 C5 H5' 109.8 . . ? O2 C5 H5' 108.5 . . ? C7' C5 H5' 114.0 . . ? C6' C5 H5' 114.0 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C5 C6' H6'1 109.5 . . ? C5 C6' H6'2 109.5 . . ? H6'1 C6' H6'2 109.5 . . ? C5 C6' H6'3 109.5 . . ? H6'1 C6' H6'3 109.5 . . ? H6'2 C6' H6'3 109.5 . . ? C5 C7' H7'1 109.5 . . ? C5 C7' H7'2 109.5 . . ? H7'1 C7' H7'2 109.5 . . ? C5 C7' H7'3 109.5 . . ? H7'1 C7' H7'3 109.5 . . ? H7'2 C7' H7'3 109.5 . . ? C13 C8 C9 122.0(3) . . ? C13 C8 N2 118.8(3) . . ? C9 C8 N2 119.1(3) . . ? C10 C9 C8 116.0(3) . . ? C10 C9 C14 122.5(3) . . ? C8 C9 C14 121.5(3) . . ? C11 C10 C9 122.3(3) . . ? C11 C10 H10 118.8 . . ? C9 C10 H10 118.8 . . ? C10 C11 C12 121.0(3) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C11 C12 C13 117.3(3) . . ? C11 C12 C15 122.0(4) . . ? C13 C12 C15 120.8(4) . . ? C8 C13 C12 121.3(3) . . ? C8 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 N1 C1 -62.3(4) . . . . ? O1 P1 N1 C1 46.7(3) . . . . ? O2' P1 N1 C1 -48.2(4) . . . . ? S1 P1 N1 C1 176.2(3) . . . . ? O1 P1 O2 C5 104.7(5) . . . . ? O2' P1 O2 C5 64.3(7) . . . . ? N1 P1 O2 C5 -148.1(5) . . . . ? S1 P1 O2 C5 -32.1(7) . . . . ? O2 P1 O2' C5 -66.3(7) . . . . ? O1 P1 O2' C5 151.9(5) . . . . ? N1 P1 O2' C5 -101.8(5) . . . . ? S1 P1 O2' C5 30.8(6) . . . . ? C8 N2 C1 N1 -174.0(3) . . . . ? C8 N2 C1 S2 6.9(5) . . . . ? P1 N1 C1 N2 2.6(5) . . . . ? P1 N1 C1 S2 -178.3(2) . . . . ? O2 P1 O1 C2 -178.7(3) . . . . ? O2' P1 O1 C2 -162.9(3) . . . . ? N1 P1 O1 C2 84.0(3) . . . . ? S1 P1 O1 C2 -41.8(3) . . . . ? P1 O1 C2 C4 -72.3(4) . . . . ? P1 O1 C2 C3 164.3(3) . . . . ? P1 O2' C5 C7 94.4(8) . . . . ? P1 O2' C5 C6 -129.5(10) . . . . ? P1 O2' C5 O2 63.1(7) . . . . ? P1 O2' C5 C7' 109.3(7) . . . . ? P1 O2' C5 C6' -145.6(7) . . . . ? P1 O2 C5 C7 136.2(6) . . . . ? P1 O2 C5 O2' -68.6(7) . . . . ? P1 O2 C5 C6 -82.0(11) . . . . ? P1 O2 C5 C7' 153.9(6) . . . . ? P1 O2 C5 C6' -104.3(8) . . . . ? C1 N2 C8 C13 79.5(5) . . . . ? C1 N2 C8 C9 -103.3(4) . . . . ? C13 C8 C9 C10 -0.4(5) . . . . ? N2 C8 C9 C10 -177.4(3) . . . . ? C13 C8 C9 C14 178.5(4) . . . . ? N2 C8 C9 C14 1.5(5) . . . . ? C8 C9 C10 C11 -0.2(5) . . . . ? C14 C9 C10 C11 -179.1(4) . . . . ? C9 C10 C11 C12 0.4(6) . . . . ? C10 C11 C12 C13 0.0(6) . . . . ? C10 C11 C12 C15 -179.7(4) . . . . ? C9 C8 C13 C12 0.8(5) . . . . ? N2 C8 C13 C12 177.8(3) . . . . ? C11 C12 C13 C8 -0.6(5) . . . . ? C15 C12 C13 C8 179.1(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O2 0.88(3) 2.35(4) 2.898(6) 120(3) . N2 H2 O2' 0.88(3) 2.41(3) 3.109(6) 137(4) . N1 H1 S2 0.875(10) 2.459(14) 3.310(3) 164(3) 3_767 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.401 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.058 # Attachment '- 5.cif' data_3 _database_code_depnum_ccdc_archive 'CCDC 818225' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H26 N3 O2 P S2' _chemical_formula_sum 'C15 H26 N3 O2 P S2' _chemical_formula_weight 375.48 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' 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 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.2581(6) _cell_length_b 13.1606(7) _cell_length_c 14.9343(8) _cell_angle_alpha 90.718(3) _cell_angle_beta 107.751(3) _cell_angle_gamma 93.285(2) _cell_volume 1916.07(18) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9125 _exptl_absorpt_correction_T_max 0.9258 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 33787 _diffrn_reflns_av_R_equivalents 0.0567 _diffrn_reflns_av_sigmaI/netI 0.0476 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.03 _reflns_number_total 6751 _reflns_number_gt 5263 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _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 _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0408P)^2^+4.4108P] 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 6751 _refine_ls_number_parameters 434 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_ref 0.1522 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.36048(11) -0.06402(8) 0.19327(7) 0.0275(2) Uani 1 1 d . . . S1 S 0.40837(13) -0.16435(10) 0.28769(9) 0.0491(3) Uani 1 1 d . . . S2 S 0.69328(12) 0.04271(10) 0.09773(7) 0.0427(3) Uani 1 1 d . . . N1 N 0.4732(3) -0.0380(3) 0.1345(2) 0.0291(8) Uani 1 1 d D . . H1 H 0.427(5) -0.040(4) 0.0722(11) 0.060(16) Uiso 1 1 d D . . N2 N 0.6668(4) -0.0105(3) 0.2620(2) 0.0365(9) Uani 1 1 d D . . H2 H 0.622(3) -0.046(3) 0.296(2) 0.023(10) Uiso 1 1 d D . . N3 N 1.2058(4) 0.1240(3) 0.4685(3) 0.0478(10) Uani 1 1 d . . . O1 O 0.2294(3) -0.0863(2) 0.1077(2) 0.0370(7) Uani 1 1 d . . . O2 O 0.3418(3) 0.0380(2) 0.2398(2) 0.0367(7) Uani 1 1 d . . . C1 C 0.6086(4) -0.0046(3) 0.1693(3) 0.0295(9) Uani 1 1 d . . . C2 C 0.1336(4) -0.1764(3) 0.0934(3) 0.0391(11) Uani 1 1 d . . . H2B H 0.1461 -0.2108 0.1545 0.047 Uiso 1 1 calc R . . C3 C -0.0058(6) -0.1378(6) 0.0599(5) 0.089(2) Uani 1 1 d . . . H3A H -0.0189 -0.0918 0.1082 0.134 Uiso 1 1 calc R . . H3B H -0.0747 -0.1952 0.0476 0.134 Uiso 1 1 calc R . . H3C H -0.0159 -0.1008 0.0019 0.134 Uiso 1 1 calc R . . C4 C 0.1664(8) -0.2462(4) 0.0255(5) 0.085(2) Uani 1 1 d . . . H4A H 0.2591 -0.2689 0.0531 0.128 Uiso 1 1 calc R . . H4B H 0.1615 -0.2104 -0.0325 0.128 Uiso 1 1 calc R . . H4C H 0.1002 -0.3054 0.0111 0.128 Uiso 1 1 calc R . . C5 C 0.3038(5) 0.1307(3) 0.1862(4) 0.0453(12) Uani 1 1 d . . . H5 H 0.2806 0.1140 0.1174 0.054 Uiso 1 1 calc R . . C6 C 0.4251(6) 0.2054(4) 0.2155(5) 0.0742(18) Uani 1 1 d . . . H6A H 0.5021 0.1772 0.1999 0.111 Uiso 1 1 calc R . . H6B H 0.4507 0.2191 0.2836 0.111 Uiso 1 1 calc R . . H6C H 0.4022 0.2689 0.1825 0.111 Uiso 1 1 calc R . . C7 C 0.1801(6) 0.1671(4) 0.2072(4) 0.0606(15) Uani 1 1 d . . . H7A H 0.1044 0.1147 0.1864 0.091 Uiso 1 1 calc R . . H7B H 0.1533 0.2299 0.1737 0.091 Uiso 1 1 calc R . . H7C H 0.2018 0.1804 0.2750 0.091 Uiso 1 1 calc R . . C8 C 0.8046(4) 0.0247(3) 0.3130(3) 0.0308(9) Uani 1 1 d . . . C9 C 0.8292(5) 0.1092(4) 0.3720(3) 0.0397(11) Uani 1 1 d . . . H9 H 0.7547 0.1464 0.3765 0.048 Uiso 1 1 calc R . . C10 C 0.9613(5) 0.1405(4) 0.4247(3) 0.0408(11) Uani 1 1 d . . . H10 H 0.9758 0.1983 0.4662 0.049 Uiso 1 1 calc R . . C11 C 1.0733(4) 0.0897(3) 0.4189(3) 0.0341(10) Uani 1 1 d . . . C12 C 1.0466(5) 0.0032(4) 0.3592(3) 0.0399(11) Uani 1 1 d . . . H12 H 1.1204 -0.0344 0.3541 0.048 Uiso 1 1 calc R . . C13 C 0.9138(4) -0.0280(3) 0.3076(3) 0.0381(10) Uani 1 1 d . . . H13 H 0.8976 -0.0871 0.2677 0.046 Uiso 1 1 calc R . . C14 C 1.3181(5) 0.0607(4) 0.4732(3) 0.0523(14) Uani 1 1 d . . . H14A H 1.3022 -0.0046 0.5002 0.079 Uiso 1 1 calc R . . H14B H 1.4040 0.0950 0.5128 0.079 Uiso 1 1 calc R . . H14C H 1.3242 0.0487 0.4098 0.079 Uiso 1 1 calc R . . C15 C 1.2286(5) 0.2067(4) 0.5372(3) 0.0469(12) Uani 1 1 d . . . H15A H 1.1883 0.2676 0.5060 0.070 Uiso 1 1 calc R . . H15B H 1.3274 0.2210 0.5667 0.070 Uiso 1 1 calc R . . H15C H 1.1857 0.1876 0.5854 0.070 Uiso 1 1 calc R . . P1A P -0.10006(11) 0.59386(9) 0.19493(7) 0.0300(3) Uani 1 1 d . A . S1A S -0.02818(14) 0.69935(10) 0.28988(8) 0.0468(3) Uani 1 1 d . . . S2A S 0.19422(11) 0.45909(9) 0.09359(7) 0.0324(3) Uani 1 1 d . . . N1A N 0.0023(3) 0.5611(3) 0.1325(2) 0.0268(7) Uani 1 1 d D . . H1A H -0.042(4) 0.550(4) 0.0702(10) 0.049(14) Uiso 1 1 d D . . N2A N 0.1953(4) 0.5413(3) 0.2569(2) 0.0362(9) Uani 1 1 d D . . H2A H 0.163(4) 0.585(3) 0.291(3) 0.040(13) Uiso 1 1 d D . . N3A N 0.6920(4) 0.3801(3) 0.4571(3) 0.0416(9) Uani 1 1 d . . . O1A O -0.1369(3) 0.4951(2) 0.24179(19) 0.0357(7) Uani 1 1 d . . . O2A O -0.2261(3) 0.6170(3) 0.1094(2) 0.0408(8) Uani 1 1 d . . . C1A C 0.1297(4) 0.5236(3) 0.1659(3) 0.0254(8) Uani 1 1 d . . . C2A C -0.1781(5) 0.3967(4) 0.1896(3) 0.0447(12) Uani 1 1 d . . . H2C H -0.1868 0.4058 0.1217 0.054 Uiso 1 1 calc R . . C3A C -0.3156(6) 0.3623(5) 0.1997(5) 0.0779(19) Uani 1 1 d . . . H3A1 H -0.3830 0.4114 0.1707 0.117 Uiso 1 1 calc R . . H3A2 H -0.3077 0.3577 0.2666 0.117 Uiso 1 1 calc R . . H3A3 H -0.3454 0.2953 0.1684 0.117 Uiso 1 1 calc R . . C4A C -0.0732(6) 0.3263(4) 0.2299(5) 0.0707(17) Uani 1 1 d . . . H4A1 H 0.0137 0.3517 0.2212 0.106 Uiso 1 1 calc R . . H4A2 H -0.1010 0.2593 0.1983 0.106 Uiso 1 1 calc R . . H4A3 H -0.0616 0.3205 0.2972 0.106 Uiso 1 1 calc R . . C5A C -0.3089(9) 0.7091(7) 0.1151(6) 0.036(2) Uiso 0.538(9) 1 d P A 1 H5A H -0.2453 0.7680 0.1475 0.043 Uiso 0.538(9) 1 calc PR A 1 C6A C -0.3780(9) 0.7333(7) 0.0141(6) 0.040(2) Uiso 0.538(9) 1 d P A 1 H6A1 H -0.3083 0.7542 -0.0158 0.060 Uiso 0.538(9) 1 calc PR A 1 H6A2 H -0.4388 0.7886 0.0115 0.060 Uiso 0.538(9) 1 calc PR A 1 H6A3 H -0.4317 0.6727 -0.0192 0.060 Uiso 0.538(9) 1 calc PR A 1 C7A C -0.3993(11) 0.6808(9) 0.1679(8) 0.063(3) Uiso 0.538(9) 1 d P A 1 H7A1 H -0.3456 0.6691 0.2330 0.095 Uiso 0.538(9) 1 calc PR A 1 H7A2 H -0.4538 0.6182 0.1400 0.095 Uiso 0.538(9) 1 calc PR A 1 H7A3 H -0.4605 0.7355 0.1668 0.095 Uiso 0.538(9) 1 calc PR A 1 C5A' C -0.3610(9) 0.6444(7) 0.1143(7) 0.034(3) Uiso 0.462(9) 1 d P A 2 H5A' H -0.3628 0.6426 0.1809 0.040 Uiso 0.462(9) 1 calc PR A 2 C6A' C -0.3634(19) 0.7520(14) 0.0831(13) 0.093(5) Uiso 0.462(9) 1 d P A 2 H6A4 H -0.2862 0.7928 0.1260 0.140 Uiso 0.462(9) 1 calc PR A 2 H6A5 H -0.4497 0.7799 0.0836 0.140 Uiso 0.462(9) 1 calc PR A 2 H6A6 H -0.3559 0.7536 0.0193 0.140 Uiso 0.462(9) 1 calc PR A 2 C7A' C -0.4758(14) 0.5805(11) 0.0538(10) 0.073(4) Uiso 0.462(9) 1 d P A 2 H7A4 H -0.4760 0.5125 0.0798 0.110 Uiso 0.462(9) 1 calc PR A 2 H7A5 H -0.4664 0.5752 -0.0094 0.110 Uiso 0.462(9) 1 calc PR A 2 H7A6 H -0.5620 0.6110 0.0504 0.110 Uiso 0.462(9) 1 calc PR A 2 C8A C 0.3227(4) 0.5009(3) 0.3077(3) 0.0320(10) Uani 1 1 d . . . C9A C 0.4461(5) 0.5496(4) 0.3094(3) 0.0418(11) Uani 1 1 d . . . H9A H 0.4470 0.6100 0.2755 0.050 Uiso 1 1 calc R . . C10A C 0.5689(5) 0.5109(4) 0.3603(3) 0.0422(11) Uani 1 1 d . . . H10A H 0.6530 0.5453 0.3605 0.051 Uiso 1 1 calc R . . C11A C 0.5710(4) 0.4228(3) 0.4109(3) 0.0330(10) Uani 1 1 d . . . C12A C 0.4450(5) 0.3766(4) 0.4106(3) 0.0380(10) Uani 1 1 d . . . H12A H 0.4431 0.3176 0.4463 0.046 Uiso 1 1 calc R . . C13A C 0.3227(5) 0.4151(4) 0.3592(3) 0.0388(11) Uani 1 1 d . . . H13A H 0.2380 0.3820 0.3595 0.047 Uiso 1 1 calc R . . C14A C 0.6898(5) 0.2947(4) 0.5167(3) 0.0458(12) Uani 1 1 d . . . H14D H 0.6556 0.3155 0.5682 0.069 Uiso 1 1 calc R . . H14E H 0.7829 0.2721 0.5427 0.069 Uiso 1 1 calc R . . H14F H 0.6295 0.2388 0.4796 0.069 Uiso 1 1 calc R . . C15A C 0.8205(4) 0.4401(4) 0.4751(3) 0.0462(12) Uani 1 1 d . . . H15D H 0.8345 0.4588 0.4153 0.069 Uiso 1 1 calc R . . H15E H 0.8960 0.4003 0.5108 0.069 Uiso 1 1 calc R . . H15F H 0.8181 0.5020 0.5116 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0293(5) 0.0292(6) 0.0228(5) 0.0040(4) 0.0069(4) -0.0033(4) S1 0.0439(7) 0.0495(8) 0.0434(7) 0.0239(6) -0.0009(5) -0.0077(5) S2 0.0327(6) 0.0707(9) 0.0246(6) 0.0036(5) 0.0109(5) -0.0094(5) N1 0.0298(18) 0.037(2) 0.0183(17) -0.0018(15) 0.0060(14) -0.0040(15) N2 0.033(2) 0.052(2) 0.0231(19) 0.0035(16) 0.0088(15) -0.0100(17) N3 0.030(2) 0.070(3) 0.039(2) -0.019(2) 0.0063(17) -0.0067(19) O1 0.0336(16) 0.0345(17) 0.0347(17) 0.0090(13) 0.0002(13) -0.0101(13) O2 0.0442(18) 0.0391(18) 0.0299(16) -0.0008(13) 0.0162(14) 0.0032(14) C1 0.032(2) 0.033(2) 0.025(2) -0.0020(17) 0.0108(18) 0.0015(17) C2 0.032(2) 0.043(3) 0.038(3) 0.008(2) 0.0079(19) -0.0133(19) C3 0.036(3) 0.105(6) 0.119(6) 0.044(5) 0.013(4) -0.009(3) C4 0.146(7) 0.041(3) 0.086(5) -0.016(3) 0.068(5) -0.023(4) C5 0.061(3) 0.031(3) 0.050(3) 0.001(2) 0.025(2) 0.006(2) C6 0.075(4) 0.039(3) 0.113(5) -0.006(3) 0.037(4) -0.001(3) C7 0.064(4) 0.049(3) 0.077(4) 0.005(3) 0.030(3) 0.017(3) C8 0.028(2) 0.041(3) 0.020(2) 0.0042(18) 0.0050(16) -0.0059(18) C9 0.035(2) 0.051(3) 0.035(2) -0.004(2) 0.013(2) 0.003(2) C10 0.040(3) 0.045(3) 0.035(3) -0.011(2) 0.010(2) -0.004(2) C11 0.032(2) 0.045(3) 0.025(2) -0.0024(19) 0.0101(18) -0.0060(19) C12 0.034(2) 0.045(3) 0.039(3) -0.006(2) 0.008(2) 0.006(2) C13 0.038(2) 0.040(3) 0.031(2) -0.0100(19) 0.0041(19) -0.003(2) C14 0.032(3) 0.085(4) 0.037(3) -0.009(3) 0.007(2) 0.002(2) C15 0.040(3) 0.055(3) 0.038(3) -0.008(2) 0.004(2) -0.013(2) P1A 0.0318(6) 0.0400(6) 0.0208(5) 0.0018(4) 0.0095(4) 0.0150(5) S1A 0.0623(8) 0.0469(7) 0.0293(6) -0.0059(5) 0.0080(6) 0.0241(6) S2A 0.0305(5) 0.0442(6) 0.0250(5) -0.0025(4) 0.0107(4) 0.0123(5) N1A 0.0270(18) 0.0347(19) 0.0195(17) 0.0014(14) 0.0066(14) 0.0105(14) N2A 0.034(2) 0.050(2) 0.0218(19) -0.0078(16) 0.0017(15) 0.0184(17) N3A 0.035(2) 0.054(3) 0.035(2) 0.0101(18) 0.0063(17) 0.0121(18) O1A 0.0384(17) 0.0463(18) 0.0262(15) 0.0001(13) 0.0151(13) 0.0041(14) O2A 0.0349(17) 0.063(2) 0.0256(16) 0.0001(14) 0.0066(13) 0.0270(15) C1A 0.029(2) 0.025(2) 0.024(2) 0.0027(16) 0.0104(17) 0.0045(16) C2A 0.051(3) 0.051(3) 0.036(3) -0.002(2) 0.021(2) -0.006(2) C3A 0.053(4) 0.096(5) 0.084(5) -0.017(4) 0.024(3) -0.014(3) C4A 0.063(4) 0.049(3) 0.090(5) -0.009(3) 0.010(3) -0.001(3) C8A 0.035(2) 0.038(2) 0.021(2) -0.0064(18) 0.0034(17) 0.0107(19) C9A 0.040(3) 0.042(3) 0.042(3) 0.007(2) 0.009(2) 0.009(2) C10A 0.030(2) 0.049(3) 0.044(3) 0.006(2) 0.006(2) 0.005(2) C11A 0.033(2) 0.045(3) 0.020(2) -0.0010(18) 0.0052(17) 0.0139(19) C12A 0.039(3) 0.044(3) 0.031(2) 0.006(2) 0.009(2) 0.011(2) C13A 0.033(2) 0.048(3) 0.035(2) -0.004(2) 0.0108(19) 0.003(2) C14A 0.048(3) 0.052(3) 0.035(3) 0.006(2) 0.006(2) 0.017(2) C15A 0.030(2) 0.066(3) 0.039(3) 0.002(2) 0.005(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 O2 1.552(3) . ? P1 O1 1.557(3) . ? P1 N1 1.675(3) . ? P1 S1 1.9162(15) . ? S2 C1 1.675(4) . ? N1 C1 1.370(5) . ? N1 H1 0.906(10) . ? N2 C1 1.335(5) . ? N2 C8 1.434(5) . ? N2 H2 0.90(3) . ? N3 C11 1.381(5) . ? N3 C15 1.444(6) . ? N3 C14 1.445(6) . ? O1 C2 1.466(5) . ? O2 C5 1.473(5) . ? C2 C4 1.485(7) . ? C2 C3 1.486(7) . ? C2 H2B 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.491(7) . ? C5 C7 1.499(7) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C9 1.372(6) . ? C8 C13 1.372(6) . ? C9 C10 1.380(6) . ? C9 H9 0.9500 . ? C10 C11 1.387(6) . ? C10 H10 0.9500 . ? C11 C12 1.398(6) . ? C12 C13 1.381(6) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? P1A O2A 1.563(3) . ? P1A O1A 1.565(3) . ? P1A N1A 1.672(3) . ? P1A S1A 1.9178(16) . ? S2A C1A 1.673(4) . ? N1A C1A 1.372(5) . ? N1A H1A 0.907(10) . ? N2A C1A 1.331(5) . ? N2A C8A 1.433(5) . ? N2A H2A 0.90(4) . ? N3A C11A 1.379(5) . ? N3A C14A 1.445(6) . ? N3A C15A 1.447(6) . ? O1A C2A 1.475(5) . ? O2A C5A' 1.473(10) . ? O2A C5A 1.536(9) . ? C2A C4A 1.453(7) . ? C2A C3A 1.508(7) . ? C2A H2C 1.0000 . ? C3A H3A1 0.9800 . ? C3A H3A2 0.9800 . ? C3A H3A3 0.9800 . ? C4A H4A1 0.9800 . ? C4A H4A2 0.9800 . ? C4A H4A3 0.9800 . ? C5A C7A 1.426(14) . ? C5A C6A 1.504(12) . ? C5A H5A 1.0000 . ? C6A H6A1 0.9800 . ? C6A H6A2 0.9800 . ? C6A H6A3 0.9800 . ? C7A H7A1 0.9800 . ? C7A H7A2 0.9800 . ? C7A H7A3 0.9800 . ? C5A' C7A' 1.459(16) . ? C5A' C6A' 1.49(2) . ? C5A' H5A' 1.0000 . ? C6A' H6A4 0.9800 . ? C6A' H6A5 0.9800 . ? C6A' H6A6 0.9800 . ? C7A' H7A4 0.9800 . ? C7A' H7A5 0.9800 . ? C7A' H7A6 0.9800 . ? C8A C13A 1.373(6) . ? C8A C9A 1.379(6) . ? C9A C10A 1.386(6) . ? C9A H9A 0.9500 . ? C10A C11A 1.390(6) . ? C10A H10A 0.9500 . ? C11A C12A 1.395(6) . ? C12A C13A 1.385(6) . ? C12A H12A 0.9500 . ? C13A H13A 0.9500 . ? C14A H14D 0.9800 . ? C14A H14E 0.9800 . ? C14A H14F 0.9800 . ? C15A H15D 0.9800 . ? C15A H15E 0.9800 . ? C15A H15F 0.9800 . ? 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 P1 O1 106.58(17) . . ? O2 P1 N1 106.56(17) . . ? O1 P1 N1 98.72(16) . . ? O2 P1 S1 109.08(13) . . ? O1 P1 S1 118.32(12) . . ? N1 P1 S1 116.45(14) . . ? C1 N1 P1 128.7(3) . . ? C1 N1 H1 122(3) . . ? P1 N1 H1 109(3) . . ? C1 N2 C8 125.4(3) . . ? C1 N2 H2 119(2) . . ? C8 N2 H2 115(2) . . ? C11 N3 C15 119.6(4) . . ? C11 N3 C14 119.9(4) . . ? C15 N3 C14 118.0(4) . . ? C2 O1 P1 126.1(3) . . ? C5 O2 P1 122.8(3) . . ? N2 C1 N1 116.5(3) . . ? N2 C1 S2 122.8(3) . . ? N1 C1 S2 120.7(3) . . ? O1 C2 C4 107.3(4) . . ? O1 C2 C3 105.8(4) . . ? C4 C2 C3 114.6(5) . . ? O1 C2 H2B 109.7 . . ? C4 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C6 107.4(4) . . ? O2 C5 C7 107.3(4) . . ? C6 C5 C7 113.5(5) . . ? O2 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C7 C5 H5 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C8 C13 118.8(4) . . ? C9 C8 N2 120.3(4) . . ? C13 C8 N2 120.9(4) . . ? C8 C9 C10 120.5(4) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C9 C10 C11 121.6(4) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? N3 C11 C10 121.5(4) . . ? N3 C11 C12 121.3(4) . . ? C10 C11 C12 117.1(4) . . ? C13 C12 C11 120.6(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C8 C13 C12 121.3(4) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? N3 C14 H14A 109.5 . . ? N3 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? N3 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O2A P1A O1A 108.73(18) . . ? O2A P1A N1A 96.82(16) . . ? O1A P1A N1A 106.92(17) . . ? O2A P1A S1A 117.60(13) . . ? O1A P1A S1A 109.23(12) . . ? N1A P1A S1A 116.54(14) . . ? C1A N1A P1A 127.3(3) . . ? C1A N1A H1A 116(3) . . ? P1A N1A H1A 114(3) . . ? C1A N2A C8A 125.2(3) . . ? C1A N2A H2A 120(3) . . ? C8A N2A H2A 115(3) . . ? C11A N3A C14A 119.5(4) . . ? C11A N3A C15A 119.4(4) . . ? C14A N3A C15A 117.1(4) . . ? C2A O1A P1A 122.4(3) . . ? C5A' O2A P1A 126.0(4) . . ? C5A O2A P1A 119.6(4) . . ? N2A C1A N1A 116.2(3) . . ? N2A C1A S2A 123.6(3) . . ? N1A C1A S2A 120.2(3) . . ? C4A C2A O1A 108.1(4) . . ? C4A C2A C3A 112.6(5) . . ? O1A C2A C3A 106.5(4) . . ? C4A C2A H2C 109.8 . . ? O1A C2A H2C 109.8 . . ? C3A C2A H2C 109.8 . . ? C2A C3A H3A1 109.5 . . ? C2A C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C2A C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C2A C4A H4A1 109.5 . . ? C2A C4A H4A2 109.5 . . ? H4A1 C4A H4A2 109.5 . . ? C2A C4A H4A3 109.5 . . ? H4A1 C4A H4A3 109.5 . . ? H4A2 C4A H4A3 109.5 . . ? C7A C5A C6A 115.2(8) . . ? C7A C5A O2A 107.6(8) . . ? C6A C5A O2A 104.4(6) . . ? C7A C5A H5A 109.8 . . ? C6A C5A H5A 109.8 . . ? O2A C5A H5A 109.8 . . ? C5A C6A H6A1 109.5 . . ? C5A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C5A C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? C5A C7A H7A1 109.5 . . ? C5A C7A H7A2 109.5 . . ? H7A1 C7A H7A2 109.5 . . ? C5A C7A H7A3 109.5 . . ? H7A1 C7A H7A3 109.5 . . ? H7A2 C7A H7A3 109.5 . . ? C7A' C5A' O2A 113.8(9) . . ? C7A' C5A' C6A' 111.8(11) . . ? O2A C5A' C6A' 101.2(9) . . ? C7A' C5A' H5A' 109.9 . . ? O2A C5A' H5A' 109.9 . . ? C6A' C5A' H5A' 109.9 . . ? C5A' C6A' H6A4 109.5 . . ? C5A' C6A' H6A5 109.5 . . ? H6A4 C6A' H6A5 109.5 . . ? C5A' C6A' H6A6 109.5 . . ? H6A4 C6A' H6A6 109.5 . . ? H6A5 C6A' H6A6 109.5 . . ? C5A' C7A' H7A4 109.5 . . ? C5A' C7A' H7A5 109.5 . . ? H7A4 C7A' H7A5 109.5 . . ? C5A' C7A' H7A6 109.5 . . ? H7A4 C7A' H7A6 109.5 . . ? H7A5 C7A' H7A6 109.5 . . ? C13A C8A C9A 119.2(4) . . ? C13A C8A N2A 119.8(4) . . ? C9A C8A N2A 120.9(4) . . ? C8A C9A C10A 120.5(4) . . ? C8A C9A H9A 119.8 . . ? C10A C9A H9A 119.8 . . ? C9A C10A C11A 121.1(4) . . ? C9A C10A H10A 119.4 . . ? C11A C10A H10A 119.4 . . ? N3A C11A C10A 121.7(4) . . ? N3A C11A C12A 120.8(4) . . ? C10A C11A C12A 117.4(4) . . ? C13A C12A C11A 121.2(4) . . ? C13A C12A H12A 119.4 . . ? C11A C12A H12A 119.4 . . ? C8A C13A C12A 120.5(4) . . ? C8A C13A H13A 119.7 . . ? C12A C13A H13A 119.7 . . ? N3A C14A H14D 109.5 . . ? N3A C14A H14E 109.5 . . ? H14D C14A H14E 109.5 . . ? N3A C14A H14F 109.5 . . ? H14D C14A H14F 109.5 . . ? H14E C14A H14F 109.5 . . ? N3A C15A H15D 109.5 . . ? N3A C15A H15E 109.5 . . ? H15D C15A H15E 109.5 . . ? N3A C15A H15F 109.5 . . ? H15D C15A H15F 109.5 . . ? H15E C15A H15F 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 N1 C1 64.4(4) . . . . ? O1 P1 N1 C1 174.7(4) . . . . ? S1 P1 N1 C1 -57.5(4) . . . . ? O2 P1 O1 C2 -120.6(3) . . . . ? N1 P1 O1 C2 129.1(4) . . . . ? S1 P1 O1 C2 2.6(4) . . . . ? O1 P1 O2 C5 -50.8(4) . . . . ? N1 P1 O2 C5 53.9(4) . . . . ? S1 P1 O2 C5 -179.6(3) . . . . ? C8 N2 C1 N1 -176.8(4) . . . . ? C8 N2 C1 S2 2.2(6) . . . . ? P1 N1 C1 N2 13.5(6) . . . . ? P1 N1 C1 S2 -165.5(2) . . . . ? P1 O1 C2 C4 -100.9(5) . . . . ? P1 O1 C2 C3 136.3(4) . . . . ? P1 O2 C5 C6 -111.2(4) . . . . ? P1 O2 C5 C7 126.5(4) . . . . ? C1 N2 C8 C9 109.2(5) . . . . ? C1 N2 C8 C13 -74.1(6) . . . . ? C13 C8 C9 C10 0.0(6) . . . . ? N2 C8 C9 C10 176.8(4) . . . . ? C8 C9 C10 C11 1.4(7) . . . . ? C15 N3 C11 C10 8.0(7) . . . . ? C14 N3 C11 C10 169.7(4) . . . . ? C15 N3 C11 C12 -173.2(4) . . . . ? C14 N3 C11 C12 -11.4(7) . . . . ? C9 C10 C11 N3 177.0(4) . . . . ? C9 C10 C11 C12 -1.9(7) . . . . ? N3 C11 C12 C13 -177.8(4) . . . . ? C10 C11 C12 C13 1.1(7) . . . . ? C9 C8 C13 C12 -0.8(7) . . . . ? N2 C8 C13 C12 -177.6(4) . . . . ? C11 C12 C13 C8 0.2(7) . . . . ? O2A P1A N1A C1A -174.5(4) . . . . ? O1A P1A N1A C1A -62.6(4) . . . . ? S1A P1A N1A C1A 59.9(4) . . . . ? O2A P1A O1A C2A 58.4(3) . . . . ? N1A P1A O1A C2A -45.2(3) . . . . ? S1A P1A O1A C2A -172.1(3) . . . . ? O1A P1A O2A C5A' 65.0(6) . . . . ? N1A P1A O2A C5A' 175.5(5) . . . . ? S1A P1A O2A C5A' -59.7(6) . . . . ? O1A P1A O2A C5A 109.8(4) . . . . ? N1A P1A O2A C5A -139.7(4) . . . . ? S1A P1A O2A C5A -14.9(5) . . . . ? C8A N2A C1A N1A 173.7(4) . . . . ? C8A N2A C1A S2A -5.9(6) . . . . ? P1A N1A C1A N2A -20.3(5) . . . . ? P1A N1A C1A S2A 159.3(2) . . . . ? P1A O1A C2A C4A 114.5(4) . . . . ? P1A O1A C2A C3A -124.3(4) . . . . ? C5A' O2A C5A C7A 31.9(8) . . . . ? P1A O2A C5A C7A -79.8(8) . . . . ? C5A' O2A C5A C6A -91.1(9) . . . . ? P1A O2A C5A C6A 157.2(5) . . . . ? C5A O2A C5A' C7A' 139.6(13) . . . . ? P1A O2A C5A' C7A' -126.9(8) . . . . ? C5A O2A C5A' C6A' 19.6(10) . . . . ? P1A O2A C5A' C6A' 113.1(9) . . . . ? C1A N2A C8A C13A -97.1(5) . . . . ? C1A N2A C8A C9A 85.9(6) . . . . ? C13A C8A C9A C10A 1.8(7) . . . . ? N2A C8A C9A C10A 178.7(4) . . . . ? C8A C9A C10A C11A -0.2(7) . . . . ? C14A N3A C11A C10A 173.5(4) . . . . ? C15A N3A C11A C10A 16.7(6) . . . . ? C14A N3A C11A C12A -8.7(6) . . . . ? C15A N3A C11A C12A -165.6(4) . . . . ? C9A C10A C11A N3A 176.0(4) . . . . ? C9A C10A C11A C12A -1.8(7) . . . . ? N3A C11A C12A C13A -175.6(4) . . . . ? C10A C11A C12A C13A 2.2(6) . . . . ? C9A C8A C13A C12A -1.4(6) . . . . ? N2A C8A C13A C12A -178.4(4) . . . . ? C11A C12A C13A C8A -0.7(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S2 0.906(10) 2.460(11) 3.365(3) 179(5) 2_655 N2 H2 S1 0.90(3) 2.58(2) 3.361(4) 145(3) . N1A H1A S2A 0.907(10) 2.467(14) 3.362(3) 169(4) 2_565 N2A H2A S1A 0.90(4) 2.53(3) 3.322(4) 146(4) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.709 _refine_diff_density_min -0.440 _refine_diff_density_rms 0.074 # Attachment '- 6.cif' data_4 _database_code_depnum_ccdc_archive 'CCDC 818226' #TrackingRef '- 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H23 N2 O4 P S2' _chemical_formula_sum 'C15 H23 N2 O4 P S2' _chemical_formula_weight 390.44 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' 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 _symmetry_space_group_name_Hall '-P 2yn' 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 7.7008(9) _cell_length_b 20.249(3) _cell_length_c 12.5512(17) _cell_angle_alpha 90.00 _cell_angle_beta 95.990(6) _cell_angle_gamma 90.00 _cell_volume 1946.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.376 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8580 _exptl_absorpt_correction_T_max 0.9185 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 52859 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 28.70 _reflns_number_total 5030 _reflns_number_gt 4241 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0357P)^2^+0.9889P] 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 5030 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0411 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 P1 P 0.25735(4) 0.639995(17) 0.11905(3) 0.02154(8) Uani 1 1 d . . . S1 S 0.22401(5) 0.68797(2) -0.01230(3) 0.03609(10) Uani 1 1 d . . . S2 S 0.09396(5) 0.440441(17) 0.13433(3) 0.03180(10) Uani 1 1 d . . . N1 N 0.15510(15) 0.56690(6) 0.10893(9) 0.0231(2) Uani 1 1 d . . . H1 H 0.100(2) 0.5596(9) 0.0481(15) 0.033(5) Uiso 1 1 d . . . N2 N 0.22443(17) 0.52962(6) 0.28050(9) 0.0272(2) Uani 1 1 d . . . H2 H 0.219(2) 0.5708(9) 0.2996(15) 0.037(5) Uiso 1 1 d . . . O1 O 0.45133(12) 0.62482(5) 0.16454(8) 0.0274(2) Uani 1 1 d . . . O2 O 0.18219(12) 0.67014(4) 0.21950(8) 0.0240(2) Uani 1 1 d . . . O3 O 0.1528(2) 0.61479(6) 0.43204(9) 0.0475(3) Uani 1 1 d . . . O4 O 0.1485(2) 0.57704(7) 0.59764(9) 0.0508(3) Uani 1 1 d . . . C1 C 0.16350(17) 0.51459(6) 0.17870(11) 0.0233(3) Uani 1 1 d . . . C2 C 0.58177(19) 0.60327(8) 0.09362(13) 0.0347(3) Uani 1 1 d . . . H2A H 0.5277 0.6040 0.0176 0.042 Uiso 1 1 calc R . . C3 C 0.7274(3) 0.65237(14) 0.1068(3) 0.0858(10) Uani 1 1 d . . . H3A H 0.6825 0.6962 0.0856 0.129 Uiso 1 1 calc R . . H3B H 0.8181 0.6397 0.0615 0.129 Uiso 1 1 calc R . . H3C H 0.7771 0.6534 0.1819 0.129 Uiso 1 1 calc R . . C4 C 0.6346(3) 0.53414(11) 0.12352(17) 0.0603(6) Uani 1 1 d . . . H4A H 0.5324 0.5051 0.1126 0.091 Uiso 1 1 calc R . . H4B H 0.6823 0.5328 0.1990 0.091 Uiso 1 1 calc R . . H4C H 0.7235 0.5192 0.0786 0.091 Uiso 1 1 calc R . . C5 C 0.20884(19) 0.74002(7) 0.25093(12) 0.0296(3) Uani 1 1 d . . . H5 H 0.2232 0.7672 0.1859 0.036 Uiso 1 1 calc R . . C6 C 0.0453(2) 0.76087(9) 0.29774(17) 0.0462(4) Uani 1 1 d . . . H6A H -0.0552 0.7559 0.2437 0.069 Uiso 1 1 calc R . . H6B H 0.0559 0.8072 0.3202 0.069 Uiso 1 1 calc R . . H6C H 0.0288 0.7331 0.3599 0.069 Uiso 1 1 calc R . . C7 C 0.3693(2) 0.74600(8) 0.32850(16) 0.0457(4) Uani 1 1 d . . . H7A H 0.4714 0.7322 0.2936 0.069 Uiso 1 1 calc R . . H7B H 0.3576 0.7177 0.3907 0.069 Uiso 1 1 calc R . . H7C H 0.3838 0.7920 0.3520 0.069 Uiso 1 1 calc R . . C8 C 0.2698(2) 0.48560(7) 0.36587(11) 0.0299(3) Uani 1 1 d . . . C9 C 0.2426(2) 0.50411(8) 0.47084(12) 0.0345(3) Uani 1 1 d . . . C10 C 0.2901(3) 0.46012(9) 0.55437(14) 0.0504(5) Uani 1 1 d . . . H10 H 0.2700 0.4718 0.6253 0.060 Uiso 1 1 calc R . . C11 C 0.3652(3) 0.40031(9) 0.53620(16) 0.0582(6) Uani 1 1 d . . . H11 H 0.3941 0.3705 0.5938 0.070 Uiso 1 1 calc R . . C12 C 0.3984(3) 0.38370(8) 0.43431(16) 0.0502(5) Uani 1 1 d . . . H12 H 0.4540 0.3429 0.4220 0.060 Uiso 1 1 calc R . . C13 C 0.3514(2) 0.42587(8) 0.34900(14) 0.0391(4) Uani 1 1 d . . . H13 H 0.3752 0.4139 0.2788 0.047 Uiso 1 1 calc R . . C14 C 0.1758(2) 0.57026(8) 0.49524(12) 0.0362(3) Uani 1 1 d . . . C15 C 0.0934(3) 0.64198(11) 0.62850(16) 0.0614(6) Uani 1 1 d . . . H15A H 0.1844 0.6743 0.6170 0.092 Uiso 1 1 calc R . . H15B H 0.0736 0.6416 0.7044 0.092 Uiso 1 1 calc R . . H15C H -0.0151 0.6540 0.5850 0.092 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.02060(15) 0.02219(16) 0.02133(16) 0.00123(12) -0.00016(12) 0.00000(12) S1 0.0401(2) 0.0383(2) 0.02852(19) 0.01208(15) -0.00245(15) -0.00545(16) S2 0.0459(2) 0.02159(17) 0.02522(18) -0.00041(13) -0.00904(15) -0.00516(14) N1 0.0269(5) 0.0222(5) 0.0191(5) -0.0002(4) -0.0034(4) -0.0005(4) N2 0.0411(7) 0.0190(6) 0.0198(5) -0.0008(4) -0.0043(5) -0.0009(5) O1 0.0211(4) 0.0357(5) 0.0247(5) -0.0064(4) -0.0007(4) 0.0033(4) O2 0.0274(5) 0.0176(4) 0.0274(5) -0.0020(4) 0.0051(4) 0.0001(3) O3 0.0828(10) 0.0337(6) 0.0276(6) 0.0002(5) 0.0135(6) 0.0049(6) O4 0.0752(9) 0.0538(8) 0.0255(6) -0.0018(5) 0.0156(6) -0.0130(7) C1 0.0249(6) 0.0222(6) 0.0220(6) -0.0008(5) -0.0014(5) 0.0011(5) C2 0.0246(7) 0.0447(9) 0.0353(8) -0.0117(7) 0.0061(6) 0.0033(6) C3 0.0397(11) 0.0863(18) 0.138(3) -0.0551(18) 0.0409(13) -0.0225(11) C4 0.0723(14) 0.0632(13) 0.0469(11) -0.0029(9) 0.0128(10) 0.0359(11) C5 0.0356(7) 0.0163(6) 0.0369(8) -0.0018(5) 0.0033(6) 0.0023(5) C6 0.0452(9) 0.0325(9) 0.0624(12) -0.0104(8) 0.0130(8) 0.0097(7) C7 0.0443(9) 0.0304(8) 0.0593(11) -0.0111(8) -0.0094(8) -0.0041(7) C8 0.0391(8) 0.0227(7) 0.0250(7) 0.0025(5) -0.0101(6) -0.0066(6) C9 0.0465(9) 0.0303(7) 0.0245(7) 0.0041(6) -0.0067(6) -0.0125(6) C10 0.0738(13) 0.0446(10) 0.0291(8) 0.0108(7) -0.0119(8) -0.0168(9) C11 0.0837(15) 0.0376(10) 0.0455(11) 0.0178(8) -0.0304(10) -0.0132(9) C12 0.0635(12) 0.0256(8) 0.0537(11) 0.0036(7) -0.0311(9) -0.0024(8) C13 0.0492(9) 0.0265(7) 0.0366(8) -0.0017(6) -0.0187(7) -0.0009(7) C14 0.0470(9) 0.0387(8) 0.0233(7) -0.0020(6) 0.0046(6) -0.0127(7) C15 0.0855(16) 0.0621(13) 0.0413(11) -0.0154(9) 0.0291(11) -0.0093(11) _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 O2 1.5651(10) . ? P1 O1 1.5729(10) . ? P1 N1 1.6750(12) . ? P1 S1 1.9076(5) . ? S2 C1 1.6700(14) . ? N1 C1 1.3717(17) . ? N1 H1 0.848(18) . ? N2 C1 1.3492(17) . ? N2 C8 1.4095(17) . ? N2 H2 0.870(19) . ? O1 C2 1.4759(17) . ? O2 C5 1.4776(16) . ? O3 C14 1.202(2) . ? O4 C14 1.3309(19) . ? O4 C15 1.447(2) . ? C2 C4 1.495(3) . ? C2 C3 1.495(3) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.496(2) . ? C5 C6 1.504(2) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 C13 1.389(2) . ? C8 C9 1.406(2) . ? C9 C10 1.395(2) . ? C9 C14 1.478(2) . ? C10 C11 1.372(3) . ? C10 H10 0.9500 . ? C11 C12 1.372(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? 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 P1 O1 101.59(5) . . ? O2 P1 N1 101.26(6) . . ? O1 P1 N1 106.02(6) . . ? O2 P1 S1 118.03(4) . . ? O1 P1 S1 116.76(4) . . ? N1 P1 S1 111.38(4) . . ? C1 N1 P1 130.05(10) . . ? C1 N1 H1 115.2(12) . . ? P1 N1 H1 114.3(12) . . ? C1 N2 C8 127.69(12) . . ? C1 N2 H2 117.0(12) . . ? C8 N2 H2 114.4(12) . . ? C2 O1 P1 121.28(9) . . ? C5 O2 P1 122.41(9) . . ? C14 O4 C15 115.63(15) . . ? N2 C1 N1 114.77(12) . . ? N2 C1 S2 125.90(11) . . ? N1 C1 S2 119.29(10) . . ? O1 C2 C4 108.05(14) . . ? O1 C2 C3 106.66(13) . . ? C4 C2 C3 114.44(19) . . ? O1 C2 H2A 109.2 . . ? C4 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C7 109.48(12) . . ? O2 C5 C6 105.93(12) . . ? C7 C5 C6 113.02(15) . . ? O2 C5 H5 109.4 . . ? C7 C5 H5 109.4 . . ? C6 C5 H5 109.4 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C13 C8 C9 119.26(14) . . ? C13 C8 N2 120.99(14) . . ? C9 C8 N2 119.62(13) . . ? C10 C9 C8 118.74(16) . . ? C10 C9 C14 119.50(15) . . ? C8 C9 C14 121.64(13) . . ? C11 C10 C9 121.39(18) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C12 119.62(16) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C11 C12 C13 120.64(18) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C12 C13 C8 120.24(17) . . ? C12 C13 H13 119.9 . . ? C8 C13 H13 119.9 . . ? O3 C14 O4 122.20(16) . . ? O3 C14 C9 124.99(14) . . ? O4 C14 C9 112.76(14) . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 N1 C1 -62.90(13) . . . . ? O1 P1 N1 C1 42.78(14) . . . . ? S1 P1 N1 C1 170.77(11) . . . . ? O2 P1 O1 C2 -171.98(11) . . . . ? N1 P1 O1 C2 82.58(12) . . . . ? S1 P1 O1 C2 -42.15(12) . . . . ? O1 P1 O2 C5 81.82(11) . . . . ? N1 P1 O2 C5 -169.02(10) . . . . ? S1 P1 O2 C5 -47.21(11) . . . . ? C8 N2 C1 N1 -170.68(14) . . . . ? C8 N2 C1 S2 11.5(2) . . . . ? P1 N1 C1 N2 19.53(19) . . . . ? P1 N1 C1 S2 -162.49(8) . . . . ? P1 O1 C2 C4 -114.46(14) . . . . ? P1 O1 C2 C3 122.05(17) . . . . ? P1 O2 C5 C7 -91.97(14) . . . . ? P1 O2 C5 C6 145.85(11) . . . . ? C1 N2 C8 C13 37.6(2) . . . . ? C1 N2 C8 C9 -146.55(15) . . . . ? C13 C8 C9 C10 -3.4(2) . . . . ? N2 C8 C9 C10 -179.32(15) . . . . ? C13 C8 C9 C14 172.64(15) . . . . ? N2 C8 C9 C14 -3.3(2) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C14 C9 C10 C11 -174.88(18) . . . . ? C9 C10 C11 C12 1.5(3) . . . . ? C10 C11 C12 C13 -2.1(3) . . . . ? C11 C12 C13 C8 -0.1(3) . . . . ? C9 C8 C13 C12 2.8(2) . . . . ? N2 C8 C13 C12 178.70(15) . . . . ? C15 O4 C14 O3 -1.4(3) . . . . ? C15 O4 C14 C9 176.29(16) . . . . ? C10 C9 C14 O3 169.75(18) . . . . ? C8 C9 C14 O3 -6.3(3) . . . . ? C10 C9 C14 O4 -7.9(2) . . . . ? C8 C9 C14 O4 176.09(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 S2 0.848(18) 2.599(19) 3.4351(12) 169.1(16) 3_565 N2 H2 O2 0.870(19) 2.253(19) 2.9557(15) 137.8(16) . N2 H2 O3 0.870(19) 1.999(19) 2.6674(17) 132.8(16) . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.342 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.046 # Attachment '- 7.cif' data_5 _database_code_depnum_ccdc_archive 'CCDC 818227' #TrackingRef '- 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H20 N3 O2 P S2' _chemical_formula_sum 'C12 H20 N3 O2 P S2' _chemical_formula_weight 333.40 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' 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 14.3388(7) _cell_length_b 6.9545(4) _cell_length_c 33.6884(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3359.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5000 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.416 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9103 _exptl_absorpt_correction_T_max 0.9596 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _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 'Siemens CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 68595 _diffrn_reflns_av_R_equivalents 0.0820 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 28.70 _reflns_number_total 4341 _reflns_number_gt 3071 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SMART (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008) ' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008) ' _computing_molecular_graphics 'XP in SHELXTL-Plus (Sheldrick, 1991)' _computing_publication_material SHELXL97 _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^)+(0.0440P)^2^+1.5254P] 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 4341 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.1030 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.013 _refine_ls_restrained_S_all 1.013 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.48464(3) 0.37493(8) 0.643903(14) 0.02762(13) Uani 1 1 d . . . S1 S 0.55292(4) 0.57887(9) 0.668186(19) 0.04817(18) Uani 1 1 d . . . S2 S 0.56146(3) 0.50631(9) 0.556353(16) 0.03680(15) Uani 1 1 d . . . O1 O 0.40072(9) 0.2904(2) 0.66826(4) 0.0357(3) Uani 1 1 d . . . O2 O 0.54185(8) 0.19365(19) 0.63147(4) 0.0289(3) Uani 1 1 d . . . N1 N 0.41897(11) 0.4320(2) 0.60458(5) 0.0276(4) Uani 1 1 d . . . H1 H 0.3637(16) 0.428(3) 0.6072(6) 0.034(6) Uiso 1 1 d . . . N2 N 0.38183(11) 0.5172(2) 0.54065(5) 0.0280(4) Uani 1 1 d . . . H2 H 0.4000(15) 0.534(3) 0.5189(7) 0.030(6) Uiso 1 1 d . . . C1 C 0.44871(13) 0.4831(3) 0.56824(6) 0.0270(4) Uani 1 1 d . . . C2 C 0.41576(15) 0.2133(4) 0.70834(6) 0.0435(6) Uani 1 1 d . . . H2A H 0.4824 0.2328 0.7162 0.052 Uiso 1 1 calc R . . C3 C 0.3949(2) 0.0042(5) 0.70702(9) 0.0787(10) Uani 1 1 d . . . H3A H 0.4378 -0.0592 0.6885 0.118 Uiso 1 1 calc R . . H3B H 0.3306 -0.0152 0.6981 0.118 Uiso 1 1 calc R . . H3C H 0.4027 -0.0510 0.7336 0.118 Uiso 1 1 calc R . . C4 C 0.3546(3) 0.3222(6) 0.73560(8) 0.1126(16) Uani 1 1 d . . . H4A H 0.3722 0.4583 0.7352 0.169 Uiso 1 1 calc R . . H4B H 0.3615 0.2717 0.7626 0.169 Uiso 1 1 calc R . . H4C H 0.2896 0.3086 0.7271 0.169 Uiso 1 1 calc R . . C5 C 0.64426(12) 0.1807(3) 0.63155(6) 0.0309(4) Uani 1 1 d . . . H5 H 0.6716 0.3120 0.6282 0.037 Uiso 1 1 calc R . . C6 C 0.67441(15) 0.0980(4) 0.67070(6) 0.0441(6) Uani 1 1 d . . . H6A H 0.6555 0.1846 0.6922 0.066 Uiso 1 1 calc R . . H6B H 0.7424 0.0834 0.6709 0.066 Uiso 1 1 calc R . . H6C H 0.6451 -0.0279 0.6745 0.066 Uiso 1 1 calc R . . C7 C 0.67046(15) 0.0579(4) 0.59665(7) 0.0445(6) Uani 1 1 d . . . H7A H 0.6490 0.1194 0.5721 0.067 Uiso 1 1 calc R . . H7B H 0.6411 -0.0688 0.5993 0.067 Uiso 1 1 calc R . . H7C H 0.7384 0.0429 0.5958 0.067 Uiso 1 1 calc R . . C8 C 0.28448(12) 0.5133(3) 0.54417(6) 0.0262(4) Uani 1 1 d . . . N3 N 0.24762(11) 0.4660(2) 0.57897(4) 0.0293(4) Uani 1 1 d . . . C12 C 0.15440(13) 0.4656(3) 0.58204(7) 0.0351(5) Uani 1 1 d . . . H12 H 0.1274 0.4314 0.6068 0.042 Uiso 1 1 calc R . . C11 C 0.09606(14) 0.5120(3) 0.55123(7) 0.0384(5) Uani 1 1 d . . . H11 H 0.0303 0.5115 0.5547 0.046 Uiso 1 1 calc R . . C10 C 0.13533(15) 0.5595(3) 0.51504(7) 0.0375(5) Uani 1 1 d . . . H10 H 0.0967 0.5917 0.4931 0.045 Uiso 1 1 calc R . . C9 C 0.23094(13) 0.5596(3) 0.51105(6) 0.0327(5) Uani 1 1 d . . . H9 H 0.2595 0.5904 0.4864 0.039 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0250(2) 0.0359(3) 0.0219(3) -0.0027(2) -0.00273(19) 0.0019(2) S1 0.0448(3) 0.0481(4) 0.0516(4) -0.0202(3) -0.0129(3) -0.0006(3) S2 0.0249(2) 0.0551(4) 0.0305(3) 0.0089(2) -0.00080(19) -0.0050(2) O1 0.0288(6) 0.0584(10) 0.0198(7) 0.0061(6) -0.0002(5) 0.0036(7) O2 0.0212(6) 0.0343(8) 0.0312(7) -0.0009(6) -0.0021(5) 0.0003(5) N1 0.0232(8) 0.0372(10) 0.0225(9) 0.0015(7) -0.0006(6) 0.0018(7) N2 0.0262(8) 0.0367(10) 0.0210(9) 0.0037(8) -0.0013(7) -0.0007(7) C1 0.0298(9) 0.0254(10) 0.0257(10) -0.0007(8) -0.0025(8) 0.0006(8) C2 0.0402(11) 0.0688(17) 0.0215(11) 0.0105(11) 0.0014(9) 0.0169(11) C3 0.089(2) 0.087(2) 0.0595(19) 0.0321(18) 0.0047(17) -0.0079(19) C4 0.155(3) 0.157(4) 0.0258(14) 0.0208(18) 0.0259(18) 0.104(3) C5 0.0192(8) 0.0392(11) 0.0344(11) 0.0039(9) -0.0006(7) 0.0010(8) C6 0.0335(11) 0.0603(15) 0.0384(13) 0.0071(11) -0.0056(9) 0.0083(11) C7 0.0379(11) 0.0541(15) 0.0414(13) -0.0019(11) 0.0043(10) 0.0140(11) C8 0.0276(8) 0.0223(9) 0.0286(10) -0.0026(8) -0.0018(7) 0.0019(7) N3 0.0279(7) 0.0311(9) 0.0288(9) -0.0012(7) -0.0009(7) 0.0033(7) C12 0.0312(10) 0.0362(12) 0.0379(12) -0.0066(9) 0.0023(9) 0.0026(9) C11 0.0270(9) 0.0426(13) 0.0456(13) -0.0103(10) -0.0052(9) 0.0038(9) C10 0.0350(10) 0.0394(12) 0.0382(13) -0.0090(10) -0.0123(9) 0.0066(9) C9 0.0340(10) 0.0352(11) 0.0289(11) -0.0033(9) -0.0061(8) 0.0058(9) _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 O2 1.5612(14) . ? P1 O1 1.5708(14) . ? P1 N1 1.6729(17) . ? P1 S1 1.9076(8) . ? S2 C1 1.6734(19) . ? O1 C2 1.469(2) . ? O2 C5 1.471(2) . ? N1 C1 1.344(2) . ? N1 H1 0.80(2) . ? N2 C1 1.356(2) . ? N2 C8 1.401(2) . ? N2 H2 0.79(2) . ? C2 C4 1.478(3) . ? C2 C3 1.485(4) . ? C2 H2A 1.0000 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C7 1.501(3) . ? C5 C6 1.502(3) . ? C5 H5 1.0000 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N3 1.327(2) . ? C8 C9 1.392(3) . ? N3 C12 1.341(2) . ? C12 C11 1.372(3) . ? C12 H12 0.9500 . ? C11 C10 1.383(3) . ? C11 H11 0.9500 . ? C10 C9 1.377(3) . ? C10 H10 0.9500 . ? C9 H9 0.9500 . ? 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 P1 O1 103.90(8) . . ? O2 P1 N1 105.95(8) . . ? O1 P1 N1 94.08(8) . . ? O2 P1 S1 116.47(6) . . ? O1 P1 S1 116.58(6) . . ? N1 P1 S1 116.88(7) . . ? C2 O1 P1 120.29(12) . . ? C5 O2 P1 125.00(12) . . ? C1 N1 P1 127.25(14) . . ? C1 N1 H1 115.2(15) . . ? P1 N1 H1 117.5(15) . . ? C1 N2 C8 130.00(18) . . ? C1 N2 H2 115.5(16) . . ? C8 N2 H2 114.3(16) . . ? N1 C1 N2 116.50(17) . . ? N1 C1 S2 123.36(14) . . ? N2 C1 S2 120.14(15) . . ? O1 C2 C4 107.28(19) . . ? O1 C2 C3 107.5(2) . . ? C4 C2 C3 113.6(3) . . ? O1 C2 H2A 109.4 . . ? C4 C2 H2A 109.4 . . ? C3 C2 H2A 109.4 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? O2 C5 C7 106.47(16) . . ? O2 C5 C6 108.20(16) . . ? C7 C5 C6 113.46(18) . . ? O2 C5 H5 109.5 . . ? C7 C5 H5 109.5 . . ? C6 C5 H5 109.5 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C5 C7 H7A 109.5 . . ? C5 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C5 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N3 C8 C9 123.07(17) . . ? N3 C8 N2 118.45(17) . . ? C9 C8 N2 118.48(18) . . ? C8 N3 C12 117.74(17) . . ? N3 C12 C11 123.3(2) . . ? N3 C12 H12 118.3 . . ? C11 C12 H12 118.3 . . ? C12 C11 C10 118.36(19) . . ? C12 C11 H11 120.8 . . ? C10 C11 H11 120.8 . . ? C9 C10 C11 119.43(19) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C10 C9 C8 118.07(19) . . ? C10 C9 H9 121.0 . . ? C8 C9 H9 121.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 P1 O1 C2 72.89(17) . . . . ? N1 P1 O1 C2 -179.56(16) . . . . ? S1 P1 O1 C2 -56.70(17) . . . . ? O1 P1 O2 C5 -139.31(14) . . . . ? N1 P1 O2 C5 122.24(14) . . . . ? S1 P1 O2 C5 -9.65(16) . . . . ? O2 P1 N1 C1 -61.61(19) . . . . ? O1 P1 N1 C1 -167.33(18) . . . . ? S1 P1 N1 C1 70.04(19) . . . . ? P1 N1 C1 N2 178.02(14) . . . . ? P1 N1 C1 S2 -2.3(3) . . . . ? C8 N2 C1 N1 2.2(3) . . . . ? C8 N2 C1 S2 -177.55(16) . . . . ? P1 O1 C2 C4 122.0(3) . . . . ? P1 O1 C2 C3 -115.4(2) . . . . ? P1 O2 C5 C7 -144.36(15) . . . . ? P1 O2 C5 C6 93.35(19) . . . . ? C1 N2 C8 N3 -1.6(3) . . . . ? C1 N2 C8 C9 178.28(19) . . . . ? C9 C8 N3 C12 -0.8(3) . . . . ? N2 C8 N3 C12 179.08(18) . . . . ? C8 N3 C12 C11 -0.2(3) . . . . ? N3 C12 C11 C10 0.8(3) . . . . ? C12 C11 C10 C9 -0.3(3) . . . . ? C11 C10 C9 C8 -0.7(3) . . . . ? N3 C8 C9 C10 1.3(3) . . . . ? N2 C8 C9 C10 -178.62(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 N3 0.80(2) 1.94(2) 2.615(2) 143(2) . N2 H2 S2 0.79(2) 2.61(2) 3.3714(18) 163(2) 5_666 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.268 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.059