Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Dr D S Wright' _publ_contact_author_address ; Department of Chemistry University of Cambridge Lensfield Road Cambridge CB2 1EW ; _publ_contact_author_email DSW1000@CAM.AC.UK _publ_section_title ; Selection of the cis and trans macrocycles [{P(m-NtBu)}2(1-Y-2-NH-C6H4)]2 (Y= O, S) ; loop_ _publ_author_name 'D. S. Wright' 'Felipe Garcia' 'Jonathan M. Goodman' 'Richard A. Kowenicki' 'M. McPartlin' ; L.Riera ; 'Maria A. Silva' 'Andreas Wirsing' data_1 _database_code_depnum_ccdc_archive 'CCDC 259069' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H46 N6 O2 P4' _chemical_formula_sum 'C28 H46 N6 O2 P4' _chemical_formula_weight 622.59 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8275(18) _cell_length_b 10.307(2) _cell_length_c 10.362(2) _cell_angle_alpha 68.10(3) _cell_angle_beta 73.40(3) _cell_angle_gamma 75.00(3) _cell_volume 825.9(3) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 10803 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.263 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.840 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_standards_number 0 _diffrn_reflns_number 6042 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_sigmaI/netI 0.0446 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 21.00 _reflns_number_total 1767 _reflns_number_gt 1542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0409P)^2^+3.5315P] 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 1767 _refine_ls_number_parameters 186 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0714 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1754 _refine_ls_wR_factor_gt 0.1728 _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_restrained_S_all 1.202 _refine_ls_shift/su_max 1.068 _refine_ls_shift/su_mean 0.011 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 0.40616(18) 0.81060(16) 0.84101(16) 0.0305(5) Uani 1 1 d . . . N1 N 0.4607(6) 0.7511(5) 0.6982(5) 0.0320(13) Uani 1 1 d . A . C1 C 0.3648(7) 0.7550(7) 0.6006(6) 0.0381(16) Uani 1 1 d . . . C11 C 0.2885(10) 0.6224(8) 0.6594(8) 0.065(2) Uani 1 1 d . A . H11A H 0.3711 0.5400 0.6678 0.097 Uiso 1 1 calc R . . H11B H 0.2254 0.6261 0.5961 0.097 Uiso 1 1 calc R . . H11C H 0.2209 0.6175 0.7513 0.097 Uiso 1 1 calc R . . C12 C 0.2353(9) 0.8849(8) 0.5868(8) 0.062(2) Uani 1 1 d . A . H12A H 0.1704 0.8824 0.6792 0.093 Uiso 1 1 calc R . . H12B H 0.1695 0.8863 0.5267 0.093 Uiso 1 1 calc R . . H12C H 0.2838 0.9686 0.5457 0.093 Uiso 1 1 calc R . . C13 C 0.4753(9) 0.7633(9) 0.4561(7) 0.064(2) Uani 1 1 d . A . H13A H 0.5190 0.8494 0.4185 0.097 Uiso 1 1 calc R . . H13B H 0.4155 0.7625 0.3923 0.097 Uiso 1 1 calc R . . H13C H 0.5609 0.6833 0.4664 0.097 Uiso 1 1 calc R . . P2 P 0.65350(18) 0.67778(17) 0.70892(17) 0.0331(5) Uani 1 1 d . A . N2 N 0.5996(6) 0.7336(5) 0.8547(5) 0.0367(13) Uani 1 1 d . A . C2 C 0.7061(7) 0.7707(6) 0.9175(7) 0.0368(16) Uani 1 1 d . . . C21 C 0.7612(9) 0.9101(7) 0.8222(7) 0.0500(19) Uani 1 1 d . A . H21A H 0.8244 0.9000 0.7331 0.075 Uiso 1 1 calc R . . H21B H 0.8247 0.9353 0.8677 0.075 Uiso 1 1 calc R . . H21C H 0.6693 0.9831 0.8055 0.075 Uiso 1 1 calc R . . C22 C 0.6120(9) 0.7811(8) 1.0635(7) 0.0516(19) Uani 1 1 d . A . H22A H 0.5164 0.8509 1.0524 0.077 Uiso 1 1 calc R . . H22B H 0.6772 0.8084 1.1057 0.077 Uiso 1 1 calc R . . H22C H 0.5833 0.6907 1.1238 0.077 Uiso 1 1 calc R . . C23 C 0.8487(8) 0.6516(7) 0.9352(8) 0.0524(19) Uani 1 1 d . A . H23A H 0.8117 0.5630 0.9890 0.079 Uiso 1 1 calc R . . H23B H 0.9151 0.6680 0.9844 0.079 Uiso 1 1 calc R . . H23C H 0.9096 0.6481 0.8432 0.079 Uiso 1 1 calc R . . N3 N 0.2984(5) 0.6872(5) 0.9639(5) 0.0303(12) Uani 0.75 1 d PD A 1 H3N H 0.356(10) 0.599(4) 0.988(10) 0.06(3) Uiso 0.75 1 d PD B 1 O1' O 0.2984(5) 0.6872(5) 0.9639(5) 0.0303(12) Uani 0.25 1 d P A 2 O1 O 0.6401(5) 0.5039(4) 0.7818(5) 0.0421(12) Uani 0.75 1 d P . 1 N3' N 0.6401(5) 0.5039(4) 0.7818(5) 0.0421(12) Uani 0.25 1 d P . 2 H3' H 0.5470 0.4805 0.8217 0.0468(5) Uiso 0.25 1 calc PR . 2 C31 C 0.1991(5) 0.7034(4) 1.0908(4) 0.0273(11) Uani 1 1 d R . . C32 C 0.0714(5) 0.8130(4) 1.0895(4) 0.0326(15) Uani 1 1 d R A . H32 H 0.0540 0.8806 1.0034 0.039 Uiso 1 1 calc R . . C33 C -0.0313(7) 0.8238(6) 1.2147(7) 0.0395(17) Uani 1 1 d . . . H33 H -0.1179 0.8980 1.2133 0.047 Uiso 1 1 calc R A . C34 C -0.0042(8) 0.7236(7) 1.3420(7) 0.0433(18) Uani 1 1 d . A . H34 H -0.0729 0.7304 1.4268 0.052 Uiso 1 1 calc R . . C35 C 0.1229(7) 0.6141(6) 1.3444(7) 0.0372(16) Uani 1 1 d . . . H35 H 0.1395 0.5466 1.4308 0.045 Uiso 1 1 calc R A . C36 C 0.2266(7) 0.6031(6) 1.2199(6) 0.0285(15) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0291(10) 0.0311(10) 0.0260(9) -0.0086(7) -0.0011(7) -0.0025(7) N1 0.035(3) 0.034(3) 0.024(3) -0.010(2) -0.009(2) 0.002(2) C1 0.042(4) 0.040(4) 0.030(4) -0.011(3) -0.010(3) -0.001(3) C11 0.086(6) 0.071(6) 0.052(5) -0.015(4) -0.033(4) -0.024(5) C12 0.058(5) 0.075(6) 0.054(5) -0.026(4) -0.030(4) 0.016(4) C13 0.067(5) 0.093(6) 0.028(4) -0.021(4) -0.011(4) -0.001(5) P2 0.0287(10) 0.0336(10) 0.0296(10) -0.0094(7) 0.0001(7) -0.0012(7) N2 0.029(3) 0.042(3) 0.040(3) -0.019(3) -0.007(2) -0.001(2) C2 0.039(4) 0.035(4) 0.040(4) -0.009(3) -0.013(3) -0.009(3) C21 0.055(5) 0.047(4) 0.051(4) -0.008(4) -0.020(4) -0.015(4) C22 0.057(5) 0.059(5) 0.048(4) -0.023(4) -0.016(4) -0.011(4) C23 0.049(4) 0.040(4) 0.075(5) -0.019(4) -0.030(4) 0.000(3) N3 0.036(3) 0.029(3) 0.022(3) -0.011(2) 0.004(2) -0.005(2) O1' 0.036(3) 0.029(3) 0.022(3) -0.011(2) 0.004(2) -0.005(2) O1 0.036(3) 0.031(3) 0.051(3) -0.010(2) -0.009(2) 0.003(2) N3' 0.036(3) 0.031(3) 0.051(3) -0.010(2) -0.009(2) 0.003(2) C31 0.0265(4) 0.0307(4) 0.024(3) -0.011(3) 0.002(3) -0.009(3) C32 0.035(4) 0.031(4) 0.027(4) -0.006(3) -0.004(3) -0.006(3) C33 0.036(4) 0.023(3) 0.049(4) -0.014(3) 0.003(3) 0.004(3) C34 0.045(4) 0.035(4) 0.043(4) -0.022(3) 0.012(3) -0.004(3) C35 0.046(4) 0.029(4) 0.032(4) -0.012(3) -0.003(3) -0.001(3) C36 0.026(3) 0.025(3) 0.035(4) -0.014(3) -0.006(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N3 1.694(5) . ? P1 N1 1.707(5) . ? P1 N2 1.709(5) . ? P1 P2 2.580(2) . ? N1 C1 1.477(8) . ? N1 P2 1.691(5) . ? C1 C12 1.509(9) . ? C1 C13 1.521(9) . ? C1 C11 1.521(10) . ? P2 O1 1.687(5) . ? P2 N2 1.714(5) . ? N2 C2 1.474(8) . ? C2 C23 1.513(9) . ? C2 C21 1.518(9) . ? C2 C22 1.532(9) . ? N3 C31 1.399(6) . ? O1 C36 1.390(7) 2_667 ? C31 C32 1.3726 . ? C31 C36 1.393(7) . ? C32 C33 1.379(7) . ? C33 C34 1.378(9) . ? C34 C35 1.369(9) . ? C35 C36 1.377(8) . ? C36 N3' 1.390(7) 2_667 ? C36 O1 1.390(7) 2_667 ? 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 N3 P1 N1 101.6(2) . . ? N3 P1 N2 103.2(3) . . ? N1 P1 N2 81.5(2) . . ? N3 P1 P2 107.23(17) . . ? N1 P1 P2 40.37(17) . . ? N2 P1 P2 41.14(18) . . ? C1 N1 P2 130.8(4) . . ? C1 N1 P1 130.3(4) . . ? P2 N1 P1 98.8(3) . . ? N1 C1 C12 108.8(5) . . ? N1 C1 C13 108.4(5) . . ? C12 C1 C13 109.8(6) . . ? N1 C1 C11 109.9(5) . . ? C12 C1 C11 109.6(6) . . ? C13 C1 C11 110.3(6) . . ? O1 P2 N1 101.1(2) . . ? O1 P2 N2 102.6(2) . . ? N1 P2 N2 81.8(2) . . ? O1 P2 P1 106.52(17) . . ? N1 P2 P1 40.84(17) . . ? N2 P2 P1 41.00(17) . . ? C2 N2 P1 128.1(4) . . ? C2 N2 P2 127.0(4) . . ? P1 N2 P2 97.9(3) . . ? N2 C2 C23 107.5(5) . . ? N2 C2 C21 110.8(5) . . ? C23 C2 C21 110.3(6) . . ? N2 C2 C22 107.6(5) . . ? C23 C2 C22 109.9(6) . . ? C21 C2 C22 110.7(6) . . ? C31 N3 P1 123.9(3) . . ? C36 O1 P2 122.7(4) 2_667 . ? C32 C31 C36 119.8(3) . . ? C32 C31 N3 121.0(3) . . ? C36 C31 N3 119.2(4) . . ? C31 C32 C33 120.6(3) . . ? C34 C33 C32 119.3(5) . . ? C35 C34 C33 120.5(6) . . ? C34 C35 C36 120.5(6) . . ? C35 C36 N3' 122.3(5) . 2_667 ? C35 C36 O1 122.3(5) . 2_667 ? N3' C36 O1 0.0(4) 2_667 2_667 ? C35 C36 C31 119.2(5) . . ? N3' C36 C31 118.5(5) 2_667 . ? O1 C36 C31 118.5(5) 2_667 . ? 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 N3 P1 N1 C1 73.7(5) . . . . ? N2 P1 N1 C1 175.5(5) . . . . ? P2 P1 N1 C1 176.7(7) . . . . ? N3 P1 N1 P2 -103.0(3) . . . . ? N2 P1 N1 P2 -1.2(3) . . . . ? P2 N1 C1 C12 -153.2(5) . . . . ? P1 N1 C1 C12 31.2(8) . . . . ? P2 N1 C1 C13 -33.8(8) . . . . ? P1 N1 C1 C13 150.5(5) . . . . ? P2 N1 C1 C11 86.8(7) . . . . ? P1 N1 C1 C11 -88.9(6) . . . . ? C1 N1 P2 O1 -74.1(5) . . . . ? P1 N1 P2 O1 102.5(3) . . . . ? C1 N1 P2 N2 -175.5(5) . . . . ? P1 N1 P2 N2 1.2(3) . . . . ? C1 N1 P2 P1 -176.7(7) . . . . ? N3 P1 P2 O1 -0.1(3) . . . . ? N1 P1 P2 O1 -87.9(3) . . . . ? N2 P1 P2 O1 90.4(3) . . . . ? N3 P1 P2 N1 87.7(3) . . . . ? N2 P1 P2 N1 178.2(4) . . . . ? N3 P1 P2 N2 -90.5(3) . . . . ? N1 P1 P2 N2 -178.2(4) . . . . ? N3 P1 N2 C2 -107.2(5) . . . . ? N1 P1 N2 C2 152.8(5) . . . . ? P2 P1 N2 C2 151.7(7) . . . . ? N3 P1 N2 P2 101.2(3) . . . . ? N1 P1 N2 P2 1.1(2) . . . . ? O1 P2 N2 C2 107.1(5) . . . . ? N1 P2 N2 C2 -153.3(5) . . . . ? P1 P2 N2 C2 -152.1(6) . . . . ? O1 P2 N2 P1 -100.7(3) . . . . ? N1 P2 N2 P1 -1.2(3) . . . . ? P1 N2 C2 C23 167.0(5) . . . . ? P2 N2 C2 C23 -49.1(7) . . . . ? P1 N2 C2 C21 -72.4(7) . . . . ? P2 N2 C2 C21 71.5(7) . . . . ? P1 N2 C2 C22 48.7(7) . . . . ? P2 N2 C2 C22 -167.3(4) . . . . ? N1 P1 N3 C31 -166.2(4) . . . . ? N2 P1 N3 C31 109.9(4) . . . . ? P2 P1 N3 C31 152.5(4) . . . . ? N1 P2 O1 C36 163.7(4) . . . 2_667 ? N2 P2 O1 C36 -112.3(5) . . . 2_667 ? P1 P2 O1 C36 -154.6(4) . . . 2_667 ? P1 N3 C31 C32 60.3(4) . . . . ? P1 N3 C31 C36 -122.5(5) . . . . ? C36 C31 C32 C33 -0.8(4) . . . . ? N3 C31 C32 C33 176.3(6) . . . . ? C31 C32 C33 C34 0.3(7) . . . . ? C32 C33 C34 C35 -0.1(10) . . . . ? C33 C34 C35 C36 0.6(10) . . . . ? C34 C35 C36 N3' 178.0(6) . . . 2_667 ? C34 C35 C36 O1 178.0(6) . . . 2_667 ? C34 C35 C36 C31 -1.1(9) . . . . ? C32 C31 C36 C35 1.2(6) . . . . ? N3 C31 C36 C35 -176.0(5) . . . . ? C32 C31 C36 N3' -177.9(3) . . . 2_667 ? N3 C31 C36 N3' 4.9(7) . . . 2_667 ? C32 C31 C36 O1 -177.9(3) . . . 2_667 ? N3 C31 C36 O1 4.9(7) . . . 2_667 ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 21.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.450 _refine_diff_density_min -0.315 _refine_diff_density_rms 0.073 data_2 _database_code_depnum_ccdc_archive 'CCDC 259070' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H46 N6 P4 S2' _chemical_formula_sum 'C28 H46 N6 P4 S2' _chemical_formula_weight 654.71 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.0091(18) _cell_length_b 9.3028(19) _cell_length_c 20.968(4) _cell_angle_alpha 87.66(3) _cell_angle_beta 89.25(3) _cell_angle_gamma 79.64(3) _cell_volume 1727.2(6) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 18046 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.367 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.907 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 22098 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0589 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 27.47 _reflns_number_total 7837 _reflns_number_gt 5622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0458P)^2^+0.7090P] 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 7837 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0745 _refine_ls_R_factor_gt 0.0443 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1021 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.002 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 0.97797(7) 0.55074(6) 0.15644(3) 0.02987(14) Uani 1 1 d . . . N1 N 0.9792(2) 0.67343(19) 0.09336(8) 0.0299(4) Uani 1 1 d . . . C1 C 1.1047(3) 0.7097(2) 0.05245(10) 0.0332(5) Uani 1 1 d . . . C11 C 1.1701(3) 0.8342(3) 0.07965(12) 0.0417(6) Uani 1 1 d . . . H11A H 1.0915 0.9218 0.0811 0.063 Uiso 1 1 calc R . . H11B H 1.2536 0.8550 0.0525 0.063 Uiso 1 1 calc R . . H11C H 1.2073 0.8059 0.1229 0.063 Uiso 1 1 calc R . . C12 C 1.0404(3) 0.7560(3) -0.01347(11) 0.0455(6) Uani 1 1 d . . . H12A H 1.0047 0.6736 -0.0321 0.068 Uiso 1 1 calc R . . H12B H 1.1191 0.7862 -0.0409 0.068 Uiso 1 1 calc R . . H12C H 0.9561 0.8380 -0.0098 0.068 Uiso 1 1 calc R . . C13 C 1.2253(3) 0.5726(3) 0.04957(12) 0.0452(6) Uani 1 1 d . . . H13A H 1.2556 0.5375 0.0930 0.068 Uiso 1 1 calc R . . H13B H 1.3132 0.5953 0.0258 0.068 Uiso 1 1 calc R . . H13C H 1.1848 0.4966 0.0280 0.068 Uiso 1 1 calc R . . P2 P 0.79080(7) 0.74608(6) 0.09294(3) 0.03044(14) Uani 1 1 d . . . N2 N 0.7895(2) 0.6260(2) 0.15654(9) 0.0327(4) Uani 1 1 d . . . C2 C 0.6630(3) 0.5512(2) 0.17665(11) 0.0340(5) Uani 1 1 d . . . C21 C 0.5197(3) 0.6634(3) 0.17675(16) 0.0590(8) Uani 1 1 d . . . H21A H 0.5294 0.7391 0.2068 0.089 Uiso 1 1 calc R . . H21B H 0.4348 0.6159 0.1897 0.089 Uiso 1 1 calc R . . H21C H 0.5016 0.7082 0.1338 0.089 Uiso 1 1 calc R . . C22 C 0.6947(4) 0.4889(4) 0.24344(15) 0.0768(11) Uani 1 1 d . . . H22A H 0.7863 0.4139 0.2434 0.115 Uiso 1 1 calc R . . H22B H 0.6094 0.4450 0.2591 0.115 Uiso 1 1 calc R . . H22C H 0.7091 0.5671 0.2714 0.115 Uiso 1 1 calc R . . C23 C 0.6478(4) 0.4335(4) 0.13126(19) 0.0886(13) Uani 1 1 d . . . H23A H 0.6298 0.4769 0.0881 0.133 Uiso 1 1 calc R . . H23B H 0.5628 0.3865 0.1446 0.133 Uiso 1 1 calc R . . H23C H 0.7409 0.3604 0.1315 0.133 Uiso 1 1 calc R . . P3 P 0.58464(7) 1.00033(7) 0.33316(3) 0.03430(15) Uani 1 1 d . . . N3 N 0.6032(2) 0.8236(2) 0.36486(9) 0.0358(4) Uani 1 1 d . . . C3 C 0.4773(3) 0.7627(3) 0.39600(12) 0.0467(7) Uani 1 1 d . . . C31 C 0.5362(4) 0.6012(3) 0.41309(17) 0.0760(11) Uani 1 1 d . . . H31A H 0.5730 0.5504 0.3744 0.114 Uiso 1 1 calc R . . H31B H 0.4545 0.5569 0.4322 0.114 Uiso 1 1 calc R . . H31C H 0.6190 0.5930 0.4437 0.114 Uiso 1 1 calc R . . C32 C 0.4246(4) 0.8421(4) 0.45643(14) 0.0656(9) Uani 1 1 d . . . H32A H 0.5088 0.8315 0.4864 0.098 Uiso 1 1 calc R . . H32B H 0.3421 0.7999 0.4761 0.098 Uiso 1 1 calc R . . H32C H 0.3891 0.9460 0.4458 0.098 Uiso 1 1 calc R . . C33 C 0.3495(3) 0.7801(4) 0.34898(15) 0.0725(10) Uani 1 1 d . . . H33A H 0.3154 0.8841 0.3381 0.109 Uiso 1 1 calc R . . H33B H 0.2657 0.7389 0.3680 0.109 Uiso 1 1 calc R . . H33C H 0.3845 0.7285 0.3102 0.109 Uiso 1 1 calc R . . P4 P 0.78083(7) 0.80961(7) 0.39647(3) 0.03423(15) Uani 1 1 d . . . N4 N 0.7636(2) 0.9816(2) 0.36233(9) 0.0349(4) Uani 1 1 d . . . C4 C 0.8676(3) 1.0875(3) 0.36215(12) 0.0443(6) Uani 1 1 d . . . C41 C 0.9764(4) 1.0456(4) 0.41687(17) 0.0788(11) Uani 1 1 d . . . H41A H 0.9196 1.0423 0.4569 0.118 Uiso 1 1 calc R . . H41B H 1.0425 1.1182 0.4192 0.118 Uiso 1 1 calc R . . H41C H 1.0375 0.9492 0.4100 0.118 Uiso 1 1 calc R . . C42 C 0.9496(4) 1.0902(4) 0.29864(15) 0.0652(9) Uani 1 1 d . . . H42A H 1.0085 0.9930 0.2913 0.098 Uiso 1 1 calc R . . H42B H 1.0173 1.1616 0.2992 0.098 Uiso 1 1 calc R . . H42C H 0.8759 1.1178 0.2643 0.098 Uiso 1 1 calc R . . C43 C 0.7753(4) 1.2383(3) 0.37371(15) 0.0622(8) Uani 1 1 d . . . H43A H 0.6945 1.2612 0.3421 0.093 Uiso 1 1 calc R . . H43B H 0.8409 1.3116 0.3698 0.093 Uiso 1 1 calc R . . H43C H 0.7312 1.2390 0.4167 0.093 Uiso 1 1 calc R . . S1 S 1.08542(7) 0.66585(6) 0.22581(3) 0.03313(14) Uani 1 1 d . . . C51 C 1.1035(2) 0.5496(2) 0.29617(10) 0.0286(5) Uani 1 1 d . . . C52 C 1.2199(3) 0.4295(2) 0.30224(12) 0.0374(5) Uani 1 1 d . . . H52 H 1.2823 0.4006 0.2665 0.045 Uiso 1 1 calc R . . C53 C 1.2455(3) 0.3518(3) 0.35989(12) 0.0439(6) Uani 1 1 d . . . H53 H 1.3250 0.2697 0.3638 0.053 Uiso 1 1 calc R . . C54 C 1.1550(3) 0.3944(3) 0.41159(12) 0.0415(6) Uani 1 1 d . . . H54 H 1.1737 0.3425 0.4515 0.050 Uiso 1 1 calc R . . C55 C 1.0375(3) 0.5114(2) 0.40626(11) 0.0361(5) Uani 1 1 d . . . H55 H 0.9753 0.5384 0.4423 0.043 Uiso 1 1 calc R . . C56 C 1.0089(2) 0.5908(2) 0.34844(10) 0.0314(5) Uani 1 1 d . . . N5 N 0.6206(3) 0.9803(2) 0.25392(10) 0.0414(5) Uani 1 1 d . . . H5N H 0.699(3) 0.935(3) 0.2442(12) 0.043(8) Uiso 1 1 d . . . S2 S 0.79954(7) 0.95850(6) 0.13245(3) 0.03487(15) Uani 1 1 d . . . C61 C 0.6040(3) 1.0330(2) 0.13967(10) 0.0319(5) Uani 1 1 d . . . C62 C 0.5188(3) 1.0898(2) 0.08643(12) 0.0394(6) Uani 1 1 d . . . H62 H 0.5645 1.0839 0.0453 0.047 Uiso 1 1 calc R . . C63 C 0.3697(3) 1.1541(3) 0.09253(13) 0.0467(6) Uani 1 1 d . . . H63 H 0.3129 1.1928 0.0559 0.056 Uiso 1 1 calc R . . C64 C 0.3031(3) 1.1622(3) 0.15208(14) 0.0489(7) Uani 1 1 d . . . H64 H 0.2005 1.2075 0.1565 0.059 Uiso 1 1 calc R . . C65 C 0.3851(3) 1.1045(3) 0.20571(12) 0.0431(6) Uani 1 1 d . . . H65 H 0.3373 1.1093 0.2464 0.052 Uiso 1 1 calc R . . C66 C 0.5362(3) 1.0399(2) 0.20055(11) 0.0340(5) Uani 1 1 d . . . N6 N 0.8917(3) 0.7099(3) 0.34173(11) 0.0508(6) Uani 1 1 d . . . H6N H 0.881(3) 0.738(3) 0.3039(13) 0.048(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0275(3) 0.0311(3) 0.0302(3) 0.0020(2) 0.0001(2) -0.0037(2) N1 0.0258(10) 0.0352(10) 0.0276(9) 0.0025(7) 0.0024(7) -0.0038(8) C1 0.0286(12) 0.0405(13) 0.0307(12) 0.0012(9) 0.0059(9) -0.0073(10) C11 0.0342(14) 0.0469(14) 0.0461(14) 0.0004(11) 0.0055(11) -0.0144(11) C12 0.0435(15) 0.0606(16) 0.0331(13) 0.0086(11) 0.0030(11) -0.0136(13) C13 0.0358(14) 0.0498(15) 0.0483(15) -0.0021(12) 0.0122(12) -0.0036(12) P2 0.0268(3) 0.0352(3) 0.0287(3) 0.0029(2) -0.0013(2) -0.0046(2) N2 0.0257(10) 0.0361(10) 0.0364(10) 0.0076(8) 0.0009(8) -0.0080(8) C2 0.0307(12) 0.0388(13) 0.0344(12) -0.0005(10) 0.0053(10) -0.0118(10) C21 0.0324(15) 0.0595(18) 0.086(2) 0.0068(15) 0.0095(14) -0.0135(14) C22 0.054(2) 0.109(3) 0.070(2) 0.0457(19) -0.0020(16) -0.0307(19) C23 0.083(3) 0.091(3) 0.111(3) -0.062(2) 0.049(2) -0.058(2) P3 0.0290(3) 0.0369(3) 0.0346(3) -0.0037(2) -0.0010(3) 0.0012(3) N3 0.0313(11) 0.0381(11) 0.0390(11) -0.0026(8) 0.0083(8) -0.0090(9) C3 0.0424(15) 0.0612(17) 0.0424(14) -0.0140(12) 0.0165(12) -0.0233(13) C31 0.094(3) 0.0596(19) 0.082(2) -0.0010(16) 0.035(2) -0.0368(19) C32 0.060(2) 0.096(2) 0.0494(17) -0.0267(16) 0.0246(15) -0.0337(18) C33 0.0513(19) 0.121(3) 0.0589(19) -0.0196(19) 0.0086(15) -0.050(2) P4 0.0326(3) 0.0363(3) 0.0312(3) 0.0048(2) 0.0032(3) -0.0009(3) N4 0.0329(11) 0.0342(10) 0.0382(11) 0.0037(8) -0.0066(8) -0.0084(9) C4 0.0473(16) 0.0484(15) 0.0413(14) 0.0038(11) -0.0076(12) -0.0208(13) C41 0.072(2) 0.092(3) 0.082(2) 0.0197(19) -0.0372(19) -0.044(2) C42 0.067(2) 0.073(2) 0.066(2) -0.0101(16) 0.0186(16) -0.0400(18) C43 0.087(2) 0.0458(16) 0.0585(18) -0.0068(13) 0.0083(17) -0.0245(16) S1 0.0322(3) 0.0377(3) 0.0296(3) 0.0016(2) -0.0007(2) -0.0073(2) C51 0.0256(11) 0.0317(11) 0.0290(11) 0.0002(9) -0.0055(9) -0.0060(9) C52 0.0324(13) 0.0365(12) 0.0416(14) -0.0073(10) -0.0010(10) 0.0000(10) C53 0.0421(15) 0.0341(13) 0.0507(16) -0.0010(11) -0.0091(12) 0.0071(11) C54 0.0467(16) 0.0376(13) 0.0383(14) 0.0046(10) -0.0104(11) -0.0031(12) C55 0.0369(14) 0.0378(13) 0.0318(12) 0.0011(10) -0.0021(10) -0.0026(11) C56 0.0265(12) 0.0320(12) 0.0341(12) 0.0014(9) -0.0025(9) -0.0012(9) N5 0.0297(12) 0.0527(13) 0.0344(11) -0.0006(9) -0.0001(9) 0.0123(10) S2 0.0320(3) 0.0344(3) 0.0375(3) 0.0008(2) 0.0006(2) -0.0046(2) C61 0.0325(13) 0.0258(11) 0.0360(12) -0.0002(9) -0.0056(10) -0.0009(9) C62 0.0474(16) 0.0348(12) 0.0350(13) 0.0015(10) -0.0066(11) -0.0049(11) C63 0.0457(16) 0.0439(14) 0.0468(16) 0.0012(11) -0.0185(12) 0.0028(12) C64 0.0339(14) 0.0469(15) 0.0604(18) -0.0072(13) -0.0137(13) 0.0096(12) C65 0.0356(14) 0.0455(14) 0.0441(15) -0.0085(11) -0.0020(11) 0.0053(11) C66 0.0345(13) 0.0299(11) 0.0356(13) -0.0021(9) -0.0063(10) 0.0000(10) N6 0.0505(15) 0.0590(14) 0.0298(12) 0.0113(10) 0.0067(10) 0.0216(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 N1 1.7126(18) . ? P1 N2 1.717(2) . ? P1 S1 2.1763(10) . ? P1 P2 2.5842(12) . ? N1 C1 1.489(3) . ? N1 P2 1.7101(19) . ? C1 C12 1.521(3) . ? C1 C13 1.523(3) . ? C1 C11 1.524(3) . ? P2 N2 1.7057(19) . ? P2 S2 2.1883(10) . ? N2 C2 1.487(3) . ? C2 C21 1.507(4) . ? C2 C22 1.505(4) . ? C2 C23 1.505(4) . ? P3 N5 1.700(2) . ? P3 N4 1.709(2) . ? P3 N3 1.728(2) . ? P3 P4 2.6029(13) . ? N3 C3 1.489(3) . ? N3 P4 1.721(2) . ? C3 C33 1.507(4) . ? C3 C32 1.520(4) . ? C3 C31 1.530(4) . ? P4 N6 1.703(2) . ? P4 N4 1.7076(19) . ? N4 C4 1.477(3) . ? C4 C41 1.511(4) . ? C4 C42 1.516(4) . ? C4 C43 1.523(4) . ? S1 C51 1.785(2) . ? C51 C52 1.391(3) . ? C51 C56 1.403(3) . ? C52 C53 1.383(3) . ? C53 C54 1.376(4) . ? C54 C55 1.377(3) . ? C55 C56 1.396(3) . ? C56 N6 1.390(3) . ? N5 C66 1.399(3) . ? S2 C61 1.780(2) . ? C61 C62 1.394(3) . ? C61 C66 1.407(3) . ? C62 C63 1.376(4) . ? C63 C64 1.377(4) . ? C64 C65 1.388(4) . ? C65 C66 1.391(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 N2 81.73(9) . . ? N1 P1 S1 97.66(7) . . ? N2 P1 S1 106.91(8) . . ? N1 P1 P2 40.94(6) . . ? N2 P1 P2 40.80(6) . . ? S1 P1 P2 106.86(4) . . ? C1 N1 P2 130.51(15) . . ? C1 N1 P1 131.42(15) . . ? P2 N1 P1 98.06(9) . . ? N1 C1 C12 107.47(19) . . ? N1 C1 C13 107.64(18) . . ? C12 C1 C13 110.9(2) . . ? N1 C1 C11 110.88(18) . . ? C12 C1 C11 109.57(19) . . ? C13 C1 C11 110.3(2) . . ? N2 P2 N1 82.12(9) . . ? N2 P2 S2 106.37(7) . . ? N1 P2 S2 99.30(7) . . ? N2 P2 P1 41.12(7) . . ? N1 P2 P1 41.01(6) . . ? S2 P2 P1 107.66(4) . . ? C2 N2 P2 126.45(15) . . ? C2 N2 P1 126.58(15) . . ? P2 N2 P1 98.08(10) . . ? N2 C2 C21 108.33(19) . . ? N2 C2 C22 107.8(2) . . ? C21 C2 C22 109.2(2) . . ? N2 C2 C23 110.4(2) . . ? C21 C2 C23 109.7(3) . . ? C22 C2 C23 111.4(3) . . ? N5 P3 N4 100.94(11) . . ? N5 P3 N3 104.59(11) . . ? N4 P3 N3 81.22(10) . . ? N5 P3 P4 108.29(8) . . ? N4 P3 P4 40.35(6) . . ? N3 P3 P4 40.91(7) . . ? C3 N3 P4 124.74(17) . . ? C3 N3 P3 123.67(17) . . ? P4 N3 P3 97.98(10) . . ? N3 C3 C33 107.8(2) . . ? N3 C3 C32 111.0(2) . . ? C33 C3 C32 110.1(3) . . ? N3 C3 C31 107.5(2) . . ? C33 C3 C31 111.1(3) . . ? C32 C3 C31 109.3(3) . . ? N6 P4 N4 101.09(11) . . ? N6 P4 N3 102.49(11) . . ? N4 P4 N3 81.45(10) . . ? N6 P4 P3 107.03(8) . . ? N4 P4 P3 40.38(7) . . ? N3 P4 P3 41.11(7) . . ? C4 N4 P4 130.50(17) . . ? C4 N4 P3 130.09(16) . . ? P4 N4 P3 99.27(10) . . ? N4 C4 C41 108.2(2) . . ? N4 C4 C42 110.6(2) . . ? C41 C4 C42 111.7(3) . . ? N4 C4 C43 108.2(2) . . ? C41 C4 C43 108.4(3) . . ? C42 C4 C43 109.7(2) . . ? C51 S1 P1 105.09(7) . . ? C52 C51 C56 119.9(2) . . ? C52 C51 S1 121.00(17) . . ? C56 C51 S1 118.66(16) . . ? C53 C52 C51 120.6(2) . . ? C54 C53 C52 119.5(2) . . ? C53 C54 C55 120.8(2) . . ? C54 C55 C56 120.7(2) . . ? N6 C56 C55 122.0(2) . . ? N6 C56 C51 119.6(2) . . ? C55 C56 C51 118.4(2) . . ? C66 N5 P3 130.70(18) . . ? C61 S2 P2 101.22(8) . . ? C62 C61 C66 119.6(2) . . ? C62 C61 S2 121.11(19) . . ? C66 C61 S2 119.22(17) . . ? C63 C62 C61 121.0(2) . . ? C64 C63 C62 119.6(2) . . ? C63 C64 C65 120.5(2) . . ? C66 C65 C64 120.8(2) . . ? C65 C66 N5 121.7(2) . . ? C65 C66 C61 118.5(2) . . ? N5 C66 C61 119.8(2) . . ? C56 N6 P4 131.81(18) . . ? 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 N2 P1 N1 C1 177.6(2) . . . . ? S1 P1 N1 C1 71.50(19) . . . . ? P2 P1 N1 C1 178.4(2) . . . . ? N2 P1 N1 P2 -0.86(9) . . . . ? S1 P1 N1 P2 -106.94(8) . . . . ? P2 N1 C1 C12 -32.9(3) . . . . ? P1 N1 C1 C12 149.16(18) . . . . ? P2 N1 C1 C13 -152.39(18) . . . . ? P1 N1 C1 C13 29.6(3) . . . . ? P2 N1 C1 C11 86.8(2) . . . . ? P1 N1 C1 C11 -91.1(2) . . . . ? C1 N1 P2 N2 -177.6(2) . . . . ? P1 N1 P2 N2 0.87(9) . . . . ? C1 N1 P2 S2 -72.19(19) . . . . ? P1 N1 P2 S2 106.27(8) . . . . ? C1 N1 P2 P1 -178.5(2) . . . . ? N1 P1 P2 N2 -178.69(14) . . . . ? S1 P1 P2 N2 -96.55(11) . . . . ? N2 P1 P2 N1 178.69(14) . . . . ? S1 P1 P2 N1 82.14(10) . . . . ? N1 P1 P2 S2 -83.82(10) . . . . ? N2 P1 P2 S2 94.88(11) . . . . ? S1 P1 P2 S2 -1.67(4) . . . . ? N1 P2 N2 C2 -149.41(19) . . . . ? S2 P2 N2 C2 113.16(18) . . . . ? P1 P2 N2 C2 -148.5(2) . . . . ? N1 P2 N2 P1 -0.87(9) . . . . ? S2 P2 N2 P1 -98.30(9) . . . . ? N1 P1 N2 C2 149.35(19) . . . . ? S1 P1 N2 C2 -115.10(17) . . . . ? P2 P1 N2 C2 148.5(2) . . . . ? N1 P1 N2 P2 0.87(9) . . . . ? S1 P1 N2 P2 96.41(8) . . . . ? P2 N2 C2 C21 -47.1(3) . . . . ? P1 N2 C2 C21 172.96(18) . . . . ? P2 N2 C2 C22 -165.2(2) . . . . ? P1 N2 C2 C22 54.9(3) . . . . ? P2 N2 C2 C23 73.0(3) . . . . ? P1 N2 C2 C23 -66.9(3) . . . . ? N5 P3 N3 C3 -117.07(19) . . . . ? N4 P3 N3 C3 143.8(2) . . . . ? P4 P3 N3 C3 141.7(2) . . . . ? N5 P3 N3 P4 101.23(11) . . . . ? N4 P3 N3 P4 2.12(9) . . . . ? P4 N3 C3 C33 -172.2(2) . . . . ? P3 N3 C3 C33 56.1(3) . . . . ? P4 N3 C3 C32 67.2(3) . . . . ? P3 N3 C3 C32 -64.5(3) . . . . ? P4 N3 C3 C31 -52.4(3) . . . . ? P3 N3 C3 C31 176.0(2) . . . . ? C3 N3 P4 N6 117.2(2) . . . . ? P3 N3 P4 N6 -101.67(11) . . . . ? C3 N3 P4 N4 -143.2(2) . . . . ? P3 N3 P4 N4 -2.12(9) . . . . ? C3 N3 P4 P3 -141.1(2) . . . . ? N5 P3 P4 N6 -1.76(13) . . . . ? N4 P3 P4 N6 -87.16(14) . . . . ? N3 P3 P4 N6 89.60(14) . . . . ? N5 P3 P4 N4 85.40(14) . . . . ? N3 P3 P4 N4 176.76(14) . . . . ? N5 P3 P4 N3 -91.36(13) . . . . ? N4 P3 P4 N3 -176.76(14) . . . . ? N6 P4 N4 C4 -80.8(2) . . . . ? N3 P4 N4 C4 178.1(2) . . . . ? P3 P4 N4 C4 175.9(3) . . . . ? N6 P4 N4 P3 103.30(12) . . . . ? N3 P4 N4 P3 2.15(10) . . . . ? N5 P3 N4 C4 78.6(2) . . . . ? N3 P3 N4 C4 -178.1(2) . . . . ? P4 P3 N4 C4 -176.0(3) . . . . ? N5 P3 N4 P4 -105.43(11) . . . . ? N3 P3 N4 P4 -2.15(10) . . . . ? P4 N4 C4 C41 -19.8(3) . . . . ? P3 N4 C4 C41 154.9(2) . . . . ? P4 N4 C4 C42 102.8(3) . . . . ? P3 N4 C4 C42 -82.5(3) . . . . ? P4 N4 C4 C43 -137.0(2) . . . . ? P3 N4 C4 C43 37.7(3) . . . . ? N1 P1 S1 C51 -177.42(10) . . . . ? N2 P1 S1 C51 98.93(10) . . . . ? P2 P1 S1 C51 141.66(8) . . . . ? P1 S1 C51 C52 80.02(19) . . . . ? P1 S1 C51 C56 -107.29(17) . . . . ? C56 C51 C52 C53 -1.4(3) . . . . ? S1 C51 C52 C53 171.17(19) . . . . ? C51 C52 C53 C54 -0.2(4) . . . . ? C52 C53 C54 C55 1.3(4) . . . . ? C53 C54 C55 C56 -0.9(4) . . . . ? C54 C55 C56 N6 -179.6(2) . . . . ? C54 C55 C56 C51 -0.7(3) . . . . ? C52 C51 C56 N6 -179.2(2) . . . . ? S1 C51 C56 N6 8.0(3) . . . . ? C52 C51 C56 C55 1.9(3) . . . . ? S1 C51 C56 C55 -170.91(17) . . . . ? N4 P3 N5 C66 -149.5(2) . . . . ? N3 P3 N5 C66 126.8(2) . . . . ? P4 P3 N5 C66 169.4(2) . . . . ? N2 P2 S2 C61 -90.66(11) . . . . ? N1 P2 S2 C61 -175.12(9) . . . . ? P1 P2 S2 C61 -133.74(8) . . . . ? P2 S2 C61 C62 -76.55(19) . . . . ? P2 S2 C61 C66 106.02(17) . . . . ? C66 C61 C62 C63 0.8(3) . . . . ? S2 C61 C62 C63 -176.63(19) . . . . ? C61 C62 C63 C64 -0.3(4) . . . . ? C62 C63 C64 C65 -0.7(4) . . . . ? C63 C64 C65 C66 1.1(4) . . . . ? C64 C65 C66 N5 -179.6(2) . . . . ? C64 C65 C66 C61 -0.5(4) . . . . ? P3 N5 C66 C65 -14.8(4) . . . . ? P3 N5 C66 C61 166.13(18) . . . . ? C62 C61 C66 C65 -0.4(3) . . . . ? S2 C61 C66 C65 177.10(17) . . . . ? C62 C61 C66 N5 178.7(2) . . . . ? S2 C61 C66 N5 -3.8(3) . . . . ? C55 C56 N6 P4 13.1(4) . . . . ? C51 C56 N6 P4 -165.8(2) . . . . ? N4 P4 N6 C56 141.9(3) . . . . ? N3 P4 N6 C56 -134.5(3) . . . . ? P3 P4 N6 C56 -176.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.303 _refine_diff_density_min -0.358 _refine_diff_density_rms 0.072 data_3 _database_code_depnum_ccdc_archive 'CCDC 259071' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 N4 O2 P2' _chemical_formula_sum 'C20 H30 N4 O2 P2' _chemical_formula_weight 420.42 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.308(2) _cell_length_b 13.578(3) _cell_length_c 15.342(3) _cell_angle_alpha 103.49(3) _cell_angle_beta 96.66(3) _cell_angle_gamma 91.07(3) _cell_volume 2272.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 18595 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.229 _exptl_cystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.838 _exptl_absorpt_correction_T_max 0.972 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 19081 _diffrn_reflns_av_R_equivalents 0.0768 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.55 _diffrn_reflns_theta_max 23.00 _reflns_number_total 6291 _reflns_number_gt 4645 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.1058P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6291 _refine_ls_number_parameters 550 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0886 _refine_ls_R_factor_gt 0.0523 _refine_ls_wR_factor_ref 0.1642 _refine_ls_wR_factor_gt 0.1427 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.065 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 0.97506(7) 0.74387(6) 0.24133(6) 0.0335(3) Uani 1 1 d . . . N1 N 0.8533(2) 0.67294(19) 0.18173(17) 0.0330(6) Uani 1 1 d . . . C1 C 0.8413(3) 0.5674(3) 0.1266(2) 0.0429(9) Uani 1 1 d . . . C11 C 0.8083(6) 0.5653(4) 0.0296(3) 0.120(2) Uani 1 1 d . . . H11A H 0.7357 0.6024 0.0225 0.179 Uiso 1 1 calc R . . H11B H 0.7941 0.4948 -0.0050 0.179 Uiso 1 1 calc R . . H11C H 0.8733 0.5972 0.0074 0.179 Uiso 1 1 calc R . . C12 C 0.7466(5) 0.5138(3) 0.1636(5) 0.120(2) Uani 1 1 d . . . H12A H 0.7623 0.5294 0.2297 0.180 Uiso 1 1 calc R . . H12B H 0.7484 0.4404 0.1395 0.180 Uiso 1 1 calc R . . H12C H 0.6680 0.5369 0.1455 0.180 Uiso 1 1 calc R . . C13 C 0.9550(4) 0.5143(3) 0.1387(3) 0.0825(15) Uani 1 1 d . . . H13A H 1.0197 0.5505 0.1200 0.124 Uiso 1 1 calc R . . H13B H 0.9454 0.4447 0.1017 0.124 Uiso 1 1 calc R . . H13C H 0.9742 0.5132 0.2024 0.124 Uiso 1 1 calc R . . P2 P 0.76543(7) 0.77031(6) 0.16876(6) 0.0320(3) Uani 1 1 d . . . N2 N 0.8756(2) 0.83812(18) 0.24521(18) 0.0318(6) Uani 1 1 d . . . C2 C 0.9066(3) 0.9477(2) 0.2528(2) 0.0419(9) Uani 1 1 d . . . C21 C 0.9502(4) 0.9616(3) 0.1661(3) 0.0625(12) Uani 1 1 d . . . H21A H 1.0205 0.9217 0.1547 0.094 Uiso 1 1 calc R . . H21B H 0.9713 1.0335 0.1723 0.094 Uiso 1 1 calc R . . H21C H 0.8870 0.9387 0.1156 0.094 Uiso 1 1 calc R . . C22 C 1.0018(4) 0.9839(3) 0.3324(3) 0.0718(14) Uani 1 1 d . . . H22A H 0.9696 0.9799 0.3882 0.108 Uiso 1 1 calc R . . H22B H 1.0271 1.0542 0.3358 0.108 Uiso 1 1 calc R . . H22C H 1.0703 0.9409 0.3248 0.108 Uiso 1 1 calc R . . C23 C 0.7921(4) 1.0038(3) 0.2680(3) 0.0627(11) Uani 1 1 d . . . H23A H 0.7325 0.9803 0.2151 0.094 Uiso 1 1 calc R . . H23B H 0.8091 1.0768 0.2774 0.094 Uiso 1 1 calc R . . H23C H 0.7614 0.9903 0.3215 0.094 Uiso 1 1 calc R . . O1 O 0.99329(18) 0.72111(16) 0.34312(14) 0.0351(6) Uani 1 1 d . . . C31 C 0.9057(3) 0.7046(2) 0.3965(2) 0.0324(8) Uani 1 1 d . . . C32 C 0.8341(3) 0.7799(3) 0.4336(2) 0.0424(9) Uani 1 1 d . . . H32 H 0.8398 0.8447 0.4205 0.051 Uiso 1 1 calc R . . C33 C 0.7533(3) 0.7613(3) 0.4904(2) 0.0520(10) Uani 1 1 d . . . H33 H 0.7046 0.8134 0.5170 0.062 Uiso 1 1 calc R . . C34 C 0.7448(3) 0.6663(3) 0.5076(2) 0.0473(10) Uani 1 1 d . . . H34 H 0.6876 0.6523 0.5444 0.057 Uiso 1 1 calc R . . C35 C 0.8184(3) 0.5915(3) 0.4720(2) 0.0440(9) Uani 1 1 d . . . H35 H 0.8115 0.5266 0.4848 0.053 Uiso 1 1 calc R . . C36 C 0.9023(3) 0.6097(2) 0.4177(2) 0.0359(8) Uani 1 1 d . . . N3 N 0.9859(3) 0.5407(3) 0.3890(2) 0.0539(9) Uani 1 1 d . . . H3NA H 1.031(3) 0.555(3) 0.352(3) 0.048(11) Uiso 1 1 d . . . H3NB H 0.968(3) 0.477(3) 0.388(2) 0.043(10) Uiso 1 1 d . . . O2 O 0.65908(18) 0.76084(17) 0.23282(14) 0.0376(6) Uani 1 1 d . . . C41 C 0.5383(3) 0.7585(2) 0.2014(2) 0.0321(8) Uani 1 1 d . . . C42 C 0.4923(3) 0.7278(3) 0.1111(2) 0.0398(8) Uani 1 1 d . . . H42 H 0.5441 0.7101 0.0659 0.048 Uiso 1 1 calc R . . C43 C 0.3690(3) 0.7230(3) 0.0871(3) 0.0453(9) Uani 1 1 d . . . H43 H 0.3368 0.7025 0.0253 0.054 Uiso 1 1 calc R . . C44 C 0.2946(3) 0.7477(3) 0.1521(3) 0.0484(10) Uani 1 1 d . . . H44 H 0.2108 0.7439 0.1353 0.058 Uiso 1 1 calc R . . C45 C 0.3406(3) 0.7783(3) 0.2425(3) 0.0437(9) Uani 1 1 d . . . H45 H 0.2880 0.7954 0.2871 0.052 Uiso 1 1 calc R . . C46 C 0.4635(3) 0.7842(2) 0.2685(2) 0.0325(8) Uani 1 1 d . . . N4 N 0.5120(3) 0.8175(2) 0.3584(2) 0.0426(7) Uani 1 1 d D . . H4NA H 0.582(2) 0.799(3) 0.373(2) 0.046(11) Uiso 1 1 d D . . H4NB H 0.463(3) 0.809(2) 0.398(2) 0.032(9) Uiso 1 1 d . . . P5 P 1.26786(7) 0.28292(6) 0.17998(6) 0.0326(3) Uani 1 1 d . . . N5 N 1.3674(2) 0.19333(19) 0.19294(17) 0.0321(6) Uani 1 1 d . . . C5 C 1.3720(3) 0.0892(2) 0.1361(2) 0.0393(8) Uani 1 1 d . . . C51 C 1.2700(4) 0.0266(3) 0.1566(4) 0.0831(16) Uani 1 1 d . . . H51A H 1.2767 0.0313 0.2217 0.125 Uiso 1 1 calc R . . H51B H 1.2740 -0.0445 0.1243 0.125 Uiso 1 1 calc R . . H51C H 1.1938 0.0526 0.1368 0.125 Uiso 1 1 calc R . . C52 C 1.3600(6) 0.0912(4) 0.0381(3) 0.106(2) Uani 1 1 d . . . H52A H 1.2858 0.1229 0.0225 0.159 Uiso 1 1 calc R . . H52B H 1.3584 0.0217 0.0010 0.159 Uiso 1 1 calc R . . H52C H 1.4279 0.1304 0.0268 0.159 Uiso 1 1 calc R . . C53 C 1.4891(3) 0.0451(3) 0.1630(3) 0.0514(10) Uani 1 1 d . . . H53A H 1.5555 0.0885 0.1553 0.077 Uiso 1 1 calc R . . H53B H 1.4934 -0.0232 0.1248 0.077 Uiso 1 1 calc R . . H53C H 1.4941 0.0416 0.2264 0.077 Uiso 1 1 calc R . . P6 P 1.47534(7) 0.27037(6) 0.26379(6) 0.0312(3) Uani 1 1 d . . . N6 N 1.3651(2) 0.35541(18) 0.26560(18) 0.0316(6) Uani 1 1 d . . . C6 C 1.3830(3) 0.4674(2) 0.2808(2) 0.0397(9) Uani 1 1 d . . . C63 C 1.2629(3) 0.5126(3) 0.2979(3) 0.0556(10) Uani 1 1 d . . . H63A H 1.2038 0.4854 0.2453 0.083 Uiso 1 1 calc R . . H63B H 1.2708 0.5865 0.3081 0.083 Uiso 1 1 calc R . . H63C H 1.2370 0.4948 0.3513 0.083 Uiso 1 1 calc R . . C61 C 1.4233(4) 0.4935(3) 0.1972(3) 0.0600(11) Uani 1 1 d . . . H61A H 1.4967 0.4592 0.1833 0.090 Uiso 1 1 calc R . . H61B H 1.4382 0.5670 0.2085 0.090 Uiso 1 1 calc R . . H61C H 1.3609 0.4711 0.1459 0.090 Uiso 1 1 calc R . . C62 C 1.4745(4) 0.5050(3) 0.3618(3) 0.0665(13) Uani 1 1 d . . . H62A H 1.4490 0.4841 0.4139 0.100 Uiso 1 1 calc R . . H62B H 1.4830 0.5791 0.3751 0.100 Uiso 1 1 calc R . . H62C H 1.5513 0.4762 0.3491 0.100 Uiso 1 1 calc R . . O5 O 1.15732(18) 0.25591(17) 0.23430(14) 0.0371(6) Uani 1 1 d . . . C71 C 1.0388(3) 0.2472(2) 0.1942(2) 0.0335(8) Uani 1 1 d . . . C72 C 1.0061(3) 0.2156(2) 0.1024(2) 0.0395(8) Uani 1 1 d . . . H72 H 1.0651 0.2015 0.0624 0.047 Uiso 1 1 calc R . . C73 C 0.8855(3) 0.2045(3) 0.0688(3) 0.0505(10) Uani 1 1 d . . . H73 H 0.8622 0.1833 0.0055 0.061 Uiso 1 1 calc R . . C74 C 0.8005(3) 0.2239(3) 0.1262(3) 0.0525(11) Uani 1 1 d . . . H74 H 0.7185 0.2163 0.1028 0.063 Uiso 1 1 calc R . . C75 C 0.8338(3) 0.2547(3) 0.2183(3) 0.0452(9) Uani 1 1 d . . . H75 H 0.7741 0.2679 0.2577 0.054 Uiso 1 1 calc R . . C76 C 0.9539(3) 0.2669(2) 0.2546(2) 0.0329(8) Uani 1 1 d . . . N7 N 0.9879(3) 0.3006(2) 0.3466(2) 0.0429(8) Uani 1 1 d . . . H7NA H 1.059(4) 0.287(3) 0.362(3) 0.057(13) Uiso 1 1 d . . . H7NB H 0.938(3) 0.286(2) 0.378(2) 0.022(9) Uiso 1 1 d . . . O6 O 1.46820(17) 0.23825(16) 0.36202(14) 0.0346(6) Uani 1 1 d . . . C81 C 1.5728(3) 0.2183(2) 0.4121(2) 0.0322(8) Uani 1 1 d . . . C82 C 1.6654(3) 0.2891(3) 0.4427(2) 0.0381(8) Uani 1 1 d . . . H82 H 1.6603 0.3540 0.4295 0.046 Uiso 1 1 calc R . . C83 C 1.7673(3) 0.2658(3) 0.4932(2) 0.0447(9) Uani 1 1 d . . . H83 H 1.8320 0.3144 0.5145 0.054 Uiso 1 1 calc R . . C84 C 1.7726(3) 0.1713(3) 0.5115(2) 0.0458(9) Uani 1 1 d . . . H84 H 1.8421 0.1545 0.5452 0.055 Uiso 1 1 calc R . . C85 C 1.6789(3) 0.1008(3) 0.4820(2) 0.0390(8) Uani 1 1 d . . . H85 H 1.6841 0.0365 0.4963 0.047 Uiso 1 1 calc R . . C86 C 1.5765(3) 0.1225(2) 0.4313(2) 0.0320(8) Uani 1 1 d . . . N8 N 1.4782(3) 0.0546(2) 0.4055(2) 0.0435(8) Uani 1 1 d D . . H8NA H 1.426(3) 0.070(2) 0.368(2) 0.037(10) Uiso 1 1 d . . . H8NB H 1.492(4) -0.0145(16) 0.392(3) 0.078(14) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0288(5) 0.0334(5) 0.0409(5) 0.0141(4) 0.0044(4) 0.0025(4) N1 0.0337(15) 0.0309(15) 0.0335(15) 0.0070(13) 0.0017(12) 0.0050(11) C1 0.045(2) 0.0341(19) 0.044(2) -0.0003(17) 0.0024(17) 0.0046(16) C11 0.222(7) 0.071(3) 0.046(3) -0.010(3) -0.025(4) 0.065(4) C12 0.105(4) 0.039(3) 0.205(7) -0.019(3) 0.081(5) -0.019(3) C13 0.089(3) 0.048(3) 0.092(4) -0.011(2) -0.016(3) 0.034(2) P2 0.0306(5) 0.0336(5) 0.0337(5) 0.0121(4) 0.0032(4) 0.0039(4) N2 0.0289(15) 0.0261(14) 0.0419(16) 0.0120(13) 0.0021(12) 0.0006(11) C2 0.049(2) 0.0264(17) 0.053(2) 0.0160(17) 0.0046(18) 0.0021(15) C21 0.071(3) 0.048(2) 0.079(3) 0.029(2) 0.023(2) 0.000(2) C22 0.080(3) 0.039(2) 0.087(3) 0.017(2) -0.024(3) -0.019(2) C23 0.070(3) 0.035(2) 0.088(3) 0.018(2) 0.018(2) 0.0117(19) O1 0.0316(12) 0.0363(12) 0.0385(13) 0.0134(11) -0.0007(10) 0.0041(9) C31 0.0285(18) 0.0381(19) 0.0286(17) 0.0075(16) -0.0041(14) 0.0018(14) C32 0.046(2) 0.042(2) 0.040(2) 0.0124(17) -0.0012(17) 0.0132(16) C33 0.046(2) 0.074(3) 0.038(2) 0.018(2) 0.0052(18) 0.024(2) C34 0.039(2) 0.068(3) 0.040(2) 0.023(2) 0.0053(17) 0.0037(18) C35 0.050(2) 0.046(2) 0.040(2) 0.0186(18) 0.0035(17) 0.0009(17) C36 0.038(2) 0.0351(19) 0.0333(18) 0.0092(16) -0.0022(15) 0.0040(15) N3 0.064(2) 0.042(2) 0.066(2) 0.0248(19) 0.0233(19) 0.0140(17) O2 0.0280(13) 0.0517(14) 0.0347(13) 0.0142(11) 0.0018(10) 0.0032(10) C41 0.0271(19) 0.0264(17) 0.043(2) 0.0114(16) -0.0022(16) 0.0012(13) C42 0.037(2) 0.043(2) 0.041(2) 0.0134(17) 0.0022(16) 0.0008(15) C43 0.046(2) 0.045(2) 0.043(2) 0.0148(18) -0.0089(18) -0.0064(17) C44 0.030(2) 0.052(2) 0.066(3) 0.025(2) -0.0064(19) -0.0009(17) C45 0.033(2) 0.044(2) 0.059(2) 0.0174(19) 0.0135(18) 0.0094(16) C46 0.0325(19) 0.0254(17) 0.041(2) 0.0098(15) 0.0050(15) 0.0019(13) N4 0.041(2) 0.0469(18) 0.0401(19) 0.0097(15) 0.0078(17) 0.0083(15) P5 0.0291(5) 0.0343(5) 0.0347(5) 0.0111(4) -0.0011(4) 0.0020(4) N5 0.0271(15) 0.0333(15) 0.0337(15) 0.0052(13) 0.0003(12) 0.0022(11) C5 0.046(2) 0.0307(18) 0.036(2) -0.0008(16) 0.0013(16) 0.0083(15) C51 0.049(3) 0.040(2) 0.150(5) 0.003(3) 0.011(3) -0.0062(19) C52 0.177(6) 0.092(4) 0.039(3) -0.002(3) -0.002(3) 0.076(4) C53 0.057(2) 0.043(2) 0.051(2) 0.0018(19) 0.0091(19) 0.0181(18) P6 0.0276(5) 0.0323(5) 0.0348(5) 0.0112(4) 0.0024(4) 0.0024(4) N6 0.0269(15) 0.0261(14) 0.0420(16) 0.0116(13) -0.0025(12) 0.0012(11) C6 0.040(2) 0.0254(17) 0.054(2) 0.0119(17) 0.0001(17) 0.0002(15) C63 0.057(2) 0.035(2) 0.076(3) 0.013(2) 0.012(2) 0.0121(17) C61 0.070(3) 0.038(2) 0.080(3) 0.024(2) 0.023(2) -0.0034(19) C62 0.075(3) 0.032(2) 0.081(3) 0.007(2) -0.023(2) -0.0081(19) O5 0.0265(13) 0.0492(14) 0.0367(13) 0.0154(11) -0.0024(10) 0.0014(10) C71 0.0279(19) 0.0253(17) 0.047(2) 0.0133(16) -0.0045(16) 0.0008(13) C72 0.037(2) 0.040(2) 0.042(2) 0.0141(17) -0.0036(16) -0.0013(15) C73 0.051(3) 0.048(2) 0.049(2) 0.019(2) -0.019(2) -0.0139(18) C74 0.033(2) 0.057(2) 0.072(3) 0.033(2) -0.011(2) -0.0087(18) C75 0.033(2) 0.043(2) 0.065(3) 0.024(2) 0.0063(18) 0.0062(16) C76 0.0302(19) 0.0251(17) 0.044(2) 0.0126(16) -0.0012(16) 0.0022(13) N7 0.036(2) 0.0461(19) 0.047(2) 0.0113(16) 0.0083(17) 0.0028(15) O6 0.0296(12) 0.0418(13) 0.0359(13) 0.0162(11) 0.0029(10) 0.0078(10) C81 0.0319(19) 0.0394(19) 0.0243(17) 0.0066(15) 0.0003(14) 0.0095(15) C82 0.040(2) 0.0373(19) 0.0353(19) 0.0075(16) 0.0025(16) 0.0010(16) C83 0.035(2) 0.057(2) 0.038(2) 0.0046(19) -0.0017(17) -0.0029(17) C84 0.039(2) 0.065(3) 0.0323(19) 0.0123(19) -0.0032(16) 0.0122(19) C85 0.045(2) 0.042(2) 0.0323(19) 0.0139(17) 0.0032(16) 0.0128(17) C86 0.0352(19) 0.0344(18) 0.0264(17) 0.0071(15) 0.0044(14) 0.0024(15) N8 0.0437(19) 0.0420(19) 0.0462(19) 0.0173(17) -0.0022(15) 0.0000(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.652(2) . ? P1 N1 1.705(3) . ? P1 N2 1.714(2) . ? P1 P2 2.5678(13) . ? N1 C1 1.479(4) . ? N1 P2 1.703(2) . ? C1 C11 1.485(5) . ? C1 C13 1.499(5) . ? C1 C12 1.517(6) . ? P2 O2 1.660(2) . ? P2 N2 1.700(3) . ? N2 C2 1.496(4) . ? C2 C22 1.512(5) . ? C2 C21 1.521(5) . ? C2 C23 1.528(5) . ? O1 C31 1.403(4) . ? C31 C32 1.375(4) . ? C31 C36 1.401(4) . ? C32 C33 1.391(5) . ? C33 C34 1.379(5) . ? C34 C35 1.379(5) . ? C35 C36 1.388(5) . ? C36 N3 1.379(4) . ? O2 C41 1.392(4) . ? C41 C42 1.385(5) . ? C41 C46 1.393(5) . ? C42 C43 1.396(5) . ? C43 C44 1.365(5) . ? C44 C45 1.386(5) . ? C45 C46 1.397(4) . ? C46 N4 1.390(4) . ? P5 O5 1.661(2) . ? P5 N5 1.702(2) . ? P5 N6 1.710(3) . ? P5 P6 2.5698(13) . ? N5 C5 1.484(4) . ? N5 P6 1.697(3) . ? C5 C52 1.501(5) . ? C5 C53 1.516(5) . ? C5 C51 1.524(5) . ? P6 O6 1.674(2) . ? P6 N6 1.713(2) . ? N6 C6 1.490(4) . ? C6 C62 1.504(5) . ? C6 C61 1.523(5) . ? C6 C63 1.526(5) . ? O5 C71 1.399(4) . ? C71 C72 1.377(5) . ? C71 C76 1.396(5) . ? C72 C73 1.393(5) . ? C73 C74 1.367(5) . ? C74 C75 1.381(5) . ? C75 C76 1.398(5) . ? C76 N7 1.384(5) . ? O6 C81 1.400(4) . ? C81 C82 1.371(5) . ? C81 C86 1.400(4) . ? C82 C83 1.396(4) . ? C83 C84 1.378(5) . ? C84 C85 1.376(5) . ? C85 C86 1.394(4) . ? C86 N8 1.389(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 N1 107.82(12) . . ? O1 P1 N2 106.52(12) . . ? N1 P1 N2 81.14(12) . . ? O1 P1 P2 119.80(9) . . ? N1 P1 P2 41.08(8) . . ? N2 P1 P2 41.03(9) . . ? C1 N1 P2 127.1(2) . . ? C1 N1 P1 131.0(2) . . ? P2 N1 P1 97.77(14) . . ? N1 C1 C11 110.7(3) . . ? N1 C1 C13 110.6(3) . . ? C11 C1 C13 109.9(4) . . ? N1 C1 C12 106.3(3) . . ? C11 C1 C12 111.9(5) . . ? C13 C1 C12 107.3(4) . . ? O2 P2 N2 102.17(12) . . ? O2 P2 N1 102.93(12) . . ? N2 P2 N1 81.60(12) . . ? O2 P2 P1 113.67(8) . . ? N2 P2 P1 41.44(9) . . ? N1 P2 P1 41.14(9) . . ? C2 N2 P2 123.5(2) . . ? C2 N2 P1 125.7(2) . . ? P2 N2 P1 97.53(14) . . ? N2 C2 C22 108.4(3) . . ? N2 C2 C21 110.3(3) . . ? C22 C2 C21 110.7(3) . . ? N2 C2 C23 106.4(3) . . ? C22 C2 C23 110.9(3) . . ? C21 C2 C23 110.0(3) . . ? C31 O1 P1 128.41(18) . . ? C32 C31 C36 121.1(3) . . ? C32 C31 O1 122.3(3) . . ? C36 C31 O1 116.3(3) . . ? C31 C32 C33 120.1(3) . . ? C34 C33 C32 119.2(3) . . ? C35 C34 C33 120.7(3) . . ? C34 C35 C36 120.9(3) . . ? N3 C36 C35 122.5(3) . . ? N3 C36 C31 119.5(3) . . ? C35 C36 C31 117.9(3) . . ? C41 O2 P2 122.72(19) . . ? C42 C41 O2 123.9(3) . . ? C42 C41 C46 121.1(3) . . ? O2 C41 C46 114.9(3) . . ? C41 C42 C43 119.3(3) . . ? C44 C43 C42 120.3(3) . . ? C43 C44 C45 120.4(3) . . ? C44 C45 C46 120.6(3) . . ? N4 C46 C41 120.0(3) . . ? N4 C46 C45 121.7(3) . . ? C41 C46 C45 118.3(3) . . ? O5 P5 N5 103.12(12) . . ? O5 P5 N6 102.31(12) . . ? N5 P5 N6 81.39(12) . . ? O5 P5 P6 113.24(8) . . ? N5 P5 P6 40.82(9) . . ? N6 P5 P6 41.39(9) . . ? C5 N5 P6 130.7(2) . . ? C5 N5 P5 128.4(2) . . ? P6 N5 P5 98.22(13) . . ? N5 C5 C52 110.1(3) . . ? N5 C5 C53 109.1(3) . . ? C52 C5 C53 110.5(3) . . ? N5 C5 C51 106.7(3) . . ? C52 C5 C51 111.4(4) . . ? C53 C5 C51 108.9(3) . . ? O6 P6 N5 102.91(12) . . ? O6 P6 N6 101.15(12) . . ? N5 P6 N6 81.45(12) . . ? O6 P6 P5 112.33(8) . . ? N5 P6 P5 40.96(8) . . ? N6 P6 P5 41.30(9) . . ? C6 N6 P5 123.61(19) . . ? C6 N6 P6 126.0(2) . . ? P5 N6 P6 97.30(14) . . ? N6 C6 C62 108.7(2) . . ? N6 C6 C61 109.9(3) . . ? C62 C6 C61 110.8(3) . . ? N6 C6 C63 106.9(3) . . ? C62 C6 C63 110.7(3) . . ? C61 C6 C63 109.8(3) . . ? C71 O5 P5 121.27(19) . . ? C72 C71 C76 121.6(3) . . ? C72 C71 O5 123.2(3) . . ? C76 C71 O5 115.1(3) . . ? C71 C72 C73 119.2(3) . . ? C74 C73 C72 120.4(4) . . ? C73 C74 C75 120.1(3) . . ? C74 C75 C76 121.2(3) . . ? N7 C76 C71 121.0(3) . . ? N7 C76 C75 121.4(3) . . ? C71 C76 C75 117.5(3) . . ? C81 O6 P6 119.78(18) . . ? C82 C81 C86 121.6(3) . . ? C82 C81 O6 122.2(3) . . ? C86 C81 O6 116.2(3) . . ? C81 C82 C83 119.9(3) . . ? C84 C83 C82 119.0(3) . . ? C85 C84 C83 121.0(3) . . ? C84 C85 C86 120.9(3) . . ? N8 C86 C85 121.6(3) . . ? N8 C86 C81 120.7(3) . . ? C85 C86 C81 117.5(3) . . ? 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 O1 P1 N1 C1 -86.9(3) . . . . ? N2 P1 N1 C1 168.5(3) . . . . ? P2 P1 N1 C1 158.0(3) . . . . ? O1 P1 N1 P2 115.19(12) . . . . ? N2 P1 N1 P2 10.59(12) . . . . ? P2 N1 C1 C11 39.5(5) . . . . ? P1 N1 C1 C11 -112.7(4) . . . . ? P2 N1 C1 C13 161.6(3) . . . . ? P1 N1 C1 C13 9.4(5) . . . . ? P2 N1 C1 C12 -82.2(4) . . . . ? P1 N1 C1 C12 125.7(4) . . . . ? C1 N1 P2 O2 89.5(3) . . . . ? P1 N1 P2 O2 -111.31(13) . . . . ? C1 N1 P2 N2 -169.9(3) . . . . ? P1 N1 P2 N2 -10.66(12) . . . . ? C1 N1 P2 P1 -159.2(3) . . . . ? O1 P1 P2 O2 -0.59(14) . . . . ? N1 P1 P2 O2 82.50(16) . . . . ? N2 P1 P2 O2 -81.44(16) . . . . ? O1 P1 P2 N2 80.85(16) . . . . ? N1 P1 P2 N2 163.94(18) . . . . ? O1 P1 P2 N1 -83.09(16) . . . . ? N2 P1 P2 N1 -163.94(18) . . . . ? O2 P2 N2 C2 -105.4(2) . . . . ? N1 P2 N2 C2 153.1(3) . . . . ? P1 P2 N2 C2 142.5(3) . . . . ? O2 P2 N2 P1 112.11(12) . . . . ? N1 P2 N2 P1 10.60(12) . . . . ? O1 P1 N2 C2 102.0(3) . . . . ? N1 P1 N2 C2 -152.0(3) . . . . ? P2 P1 N2 C2 -141.4(3) . . . . ? O1 P1 N2 P2 -116.67(12) . . . . ? N1 P1 N2 P2 -10.60(12) . . . . ? P2 N2 C2 C22 175.7(3) . . . . ? P1 N2 C2 C22 -52.3(4) . . . . ? P2 N2 C2 C21 -63.0(3) . . . . ? P1 N2 C2 C21 69.1(3) . . . . ? P2 N2 C2 C23 56.3(4) . . . . ? P1 N2 C2 C23 -171.7(2) . . . . ? N1 P1 O1 C31 -37.1(3) . . . . ? N2 P1 O1 C31 48.7(3) . . . . ? P2 P1 O1 C31 6.2(3) . . . . ? P1 O1 C31 C32 -68.3(4) . . . . ? P1 O1 C31 C36 117.7(3) . . . . ? C36 C31 C32 C33 -2.5(5) . . . . ? O1 C31 C32 C33 -176.2(3) . . . . ? C31 C32 C33 C34 -1.1(5) . . . . ? C32 C33 C34 C35 2.5(5) . . . . ? C33 C34 C35 C36 -0.3(5) . . . . ? C34 C35 C36 N3 172.7(3) . . . . ? C34 C35 C36 C31 -3.2(5) . . . . ? C32 C31 C36 N3 -171.4(3) . . . . ? O1 C31 C36 N3 2.6(4) . . . . ? C32 C31 C36 C35 4.6(5) . . . . ? O1 C31 C36 C35 178.7(3) . . . . ? N2 P2 O2 C41 147.2(2) . . . . ? N1 P2 O2 C41 -128.8(2) . . . . ? P1 P2 O2 C41 -170.82(19) . . . . ? P2 O2 C41 C42 24.1(4) . . . . ? P2 O2 C41 C46 -159.5(2) . . . . ? O2 C41 C42 C43 176.5(3) . . . . ? C46 C41 C42 C43 0.4(5) . . . . ? C41 C42 C43 C44 -0.5(5) . . . . ? C42 C43 C44 C45 0.4(5) . . . . ? C43 C44 C45 C46 -0.1(5) . . . . ? C42 C41 C46 N4 -178.2(3) . . . . ? O2 C41 C46 N4 5.3(4) . . . . ? C42 C41 C46 C45 -0.1(4) . . . . ? O2 C41 C46 C45 -176.6(2) . . . . ? C44 C45 C46 N4 178.1(3) . . . . ? C44 C45 C46 C41 0.0(5) . . . . ? O5 P5 N5 C5 86.7(3) . . . . ? N6 P5 N5 C5 -172.6(3) . . . . ? P6 P5 N5 C5 -162.9(3) . . . . ? O5 P5 N5 P6 -110.48(13) . . . . ? N6 P5 N5 P6 -9.76(12) . . . . ? P6 N5 C5 C52 -109.6(4) . . . . ? P5 N5 C5 C52 47.8(4) . . . . ? P6 N5 C5 C53 11.8(4) . . . . ? P5 N5 C5 C53 169.2(2) . . . . ? P6 N5 C5 C51 129.3(3) . . . . ? P5 N5 C5 C51 -73.3(4) . . . . ? C5 N5 P6 O6 -88.4(3) . . . . ? P5 N5 P6 O6 109.30(12) . . . . ? C5 N5 P6 N6 172.0(3) . . . . ? P5 N5 P6 N6 9.74(12) . . . . ? C5 N5 P6 P5 162.3(3) . . . . ? O5 P5 P6 O6 -0.83(13) . . . . ? N5 P5 P6 O6 -83.99(16) . . . . ? N6 P5 P6 O6 81.33(15) . . . . ? O5 P5 P6 N5 83.16(16) . . . . ? N6 P5 P6 N5 165.32(18) . . . . ? O5 P5 P6 N6 -82.16(16) . . . . ? N5 P5 P6 N6 -165.32(18) . . . . ? O5 P5 N6 C6 -105.8(2) . . . . ? N5 P5 N6 C6 152.5(3) . . . . ? P6 P5 N6 C6 142.9(3) . . . . ? O5 P5 N6 P6 111.30(12) . . . . ? N5 P5 N6 P6 9.64(12) . . . . ? O6 P6 N6 C6 107.2(3) . . . . ? N5 P6 N6 C6 -151.3(3) . . . . ? P5 P6 N6 C6 -141.6(3) . . . . ? O6 P6 N6 P5 -111.24(12) . . . . ? N5 P6 N6 P5 -9.67(12) . . . . ? P5 N6 C6 C62 179.9(3) . . . . ? P6 N6 C6 C62 -47.8(4) . . . . ? P5 N6 C6 C61 -58.7(3) . . . . ? P6 N6 C6 C61 73.6(3) . . . . ? P5 N6 C6 C63 60.4(3) . . . . ? P6 N6 C6 C63 -167.3(2) . . . . ? N5 P5 O5 C71 -130.6(2) . . . . ? N6 P5 O5 C71 145.5(2) . . . . ? P6 P5 O5 C71 -172.43(19) . . . . ? P5 O5 C71 C72 29.6(4) . . . . ? P5 O5 C71 C76 -154.2(2) . . . . ? C76 C71 C72 C73 1.0(5) . . . . ? O5 C71 C72 C73 177.0(3) . . . . ? C71 C72 C73 C74 -0.5(5) . . . . ? C72 C73 C74 C75 0.0(5) . . . . ? C73 C74 C75 C76 0.2(5) . . . . ? C72 C71 C76 N7 -178.7(3) . . . . ? O5 C71 C76 N7 5.0(4) . . . . ? C72 C71 C76 C75 -0.8(4) . . . . ? O5 C71 C76 C75 -177.1(2) . . . . ? C74 C75 C76 N7 178.1(3) . . . . ? C74 C75 C76 C71 0.3(5) . . . . ? N5 P6 O6 C81 131.8(2) . . . . ? N6 P6 O6 C81 -144.6(2) . . . . ? P5 P6 O6 C81 173.7(2) . . . . ? P6 O6 C81 C82 59.2(4) . . . . ? P6 O6 C81 C86 -122.3(2) . . . . ? C86 C81 C82 C83 0.9(5) . . . . ? O6 C81 C82 C83 179.3(3) . . . . ? C81 C82 C83 C84 -0.1(5) . . . . ? C82 C83 C84 C85 -0.9(5) . . . . ? C83 C84 C85 C86 1.0(5) . . . . ? C84 C85 C86 N8 -176.1(3) . . . . ? C84 C85 C86 C81 -0.2(5) . . . . ? C82 C81 C86 N8 175.2(3) . . . . ? O6 C81 C86 N8 -3.3(4) . . . . ? C82 C81 C86 C85 -0.8(5) . . . . ? O6 C81 C86 C85 -179.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 23.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.607 _refine_diff_density_min -0.518 _refine_diff_density_rms 0.160 data_4 _database_code_depnum_ccdc_archive 'CCDC 259072' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 N4 P2 S2' _chemical_formula_sum 'C20 H30 N4 P2 S2' _chemical_formula_weight 452.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.756(3) _cell_length_b 9.0309(18) _cell_length_c 17.947(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.74(3) _cell_angle_gamma 90.00 _cell_volume 2369.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 11238 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.373 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.985 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_reflns_number 17832 _diffrn_reflns_av_R_equivalents 0.0559 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5395 _reflns_number_gt 3533 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution 'SIR-92 (Altomare et al. 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0759P)^2^+2.0077P] 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 5395 _refine_ls_number_parameters 272 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0988 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1696 _refine_ls_wR_factor_gt 0.1450 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.077 _refine_ls_shift/su_mean 0.003 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 0.77953(5) 0.42085(9) -0.00638(4) 0.0374(2) Uani 1 1 d . . . N1 N 0.69093(16) 0.3309(3) -0.05889(13) 0.0391(6) Uani 1 1 d . . . C1 C 0.6409(2) 0.1952(3) -0.04185(18) 0.0444(7) Uani 1 1 d . . . C11 C 0.5486(2) 0.2400(5) -0.0171(2) 0.0642(10) Uani 1 1 d . . . H11A H 0.5596 0.3034 0.0275 0.096 Uiso 1 1 calc R . . H11B H 0.5155 0.1509 -0.0051 0.096 Uiso 1 1 calc R . . H11C H 0.5121 0.2941 -0.0579 0.096 Uiso 1 1 calc R . . C12 C 0.6991(3) 0.1093(4) 0.0199(2) 0.0576(9) Uani 1 1 d . . . H12A H 0.7583 0.0856 0.0037 0.086 Uiso 1 1 calc R . . H12B H 0.6677 0.0174 0.0301 0.086 Uiso 1 1 calc R . . H12C H 0.7089 0.1695 0.0657 0.086 Uiso 1 1 calc R . . C13 C 0.6243(3) 0.1011(4) -0.11265(19) 0.0532(8) Uani 1 1 d . . . H13A H 0.5863 0.1563 -0.1522 0.080 Uiso 1 1 calc R . . H13B H 0.5929 0.0095 -0.1018 0.080 Uiso 1 1 calc R . . H13C H 0.6830 0.0768 -0.1295 0.080 Uiso 1 1 calc R . . P2 P 0.69506(5) 0.41873(9) -0.14283(4) 0.0375(2) Uani 1 1 d . . . N2 N 0.77918(16) 0.5146(3) -0.08883(14) 0.0383(6) Uani 1 1 d . . . C2 C 0.8387(2) 0.6351(3) -0.11027(18) 0.0417(7) Uani 1 1 d . . . C21 C 0.7956(3) 0.7855(4) -0.0983(2) 0.0624(10) Uani 1 1 d . . . H21A H 0.7339 0.7892 -0.1262 0.094 Uiso 1 1 calc R . . H21B H 0.8331 0.8640 -0.1163 0.094 Uiso 1 1 calc R . . H21C H 0.7924 0.8000 -0.0446 0.094 Uiso 1 1 calc R . . C22 C 0.8509(2) 0.6164(4) -0.19236(19) 0.0553(9) Uani 1 1 d . . . H22A H 0.8808 0.5215 -0.1992 0.083 Uiso 1 1 calc R . . H22B H 0.8888 0.6973 -0.2075 0.083 Uiso 1 1 calc R . . H22C H 0.7909 0.6185 -0.2234 0.083 Uiso 1 1 calc R . . C23 C 0.9314(2) 0.6217(4) -0.0622(2) 0.0565(9) Uani 1 1 d . . . H23A H 0.9237 0.6301 -0.0090 0.085 Uiso 1 1 calc R . . H23B H 0.9717 0.7009 -0.0755 0.085 Uiso 1 1 calc R . . H23C H 0.9585 0.5253 -0.0712 0.085 Uiso 1 1 calc R . . S1 S 0.71924(6) 0.57702(10) 0.06532(5) 0.0554(3) Uani 1 1 d . . . C31 C 0.7828(2) 0.5294(4) 0.15364(18) 0.0474(8) Uani 1 1 d . . . C32 C 0.7458(2) 0.4346(4) 0.2021(2) 0.0514(8) Uani 1 1 d D . . C33 C 0.7950(3) 0.4090(4) 0.2743(2) 0.0603(10) Uani 1 1 d . . . H33 H 0.7693 0.3479 0.3091 0.072 Uiso 1 1 calc R . . C34 C 0.8787(3) 0.4713(5) 0.2943(2) 0.0649(10) Uani 1 1 d . . . H34 H 0.9105 0.4526 0.3430 0.078 Uiso 1 1 calc R . . C35 C 0.9180(3) 0.5599(5) 0.2461(2) 0.0642(10) Uani 1 1 d . . . H35 H 0.9775 0.5996 0.2602 0.077 Uiso 1 1 calc R . . C36 C 0.8694(3) 0.5914(4) 0.1756(2) 0.0570(9) Uani 1 1 d . . . H36 H 0.8953 0.6555 0.1422 0.068 Uiso 1 1 calc R . . N3 N 0.6654(3) 0.3653(5) 0.1802(2) 0.0822(11) Uani 1 1 d D . . H1N H 0.640(2) 0.318(4) 0.2199(17) 0.099 Uiso 1 1 d D . . H2N H 0.6257(19) 0.425(4) 0.1441(19) 0.099 Uiso 1 1 d D . . S2 S 0.57653(6) 0.56541(11) -0.15507(5) 0.0548(3) Uani 1 1 d . . . C41 C 0.5465(2) 0.5587(4) -0.2538(2) 0.0524(9) Uani 1 1 d . . . C42 C 0.4836(3) 0.4640(5) -0.2877(3) 0.0722(12) Uani 1 1 d D . . C43 C 0.4568(4) 0.4771(6) -0.3712(3) 0.0917(16) Uani 1 1 d . . . H43 H 0.4114 0.4164 -0.3985 0.110 Uiso 1 1 calc R . . C44 C 0.5025(4) 0.5820(6) -0.4041(3) 0.0815(14) Uani 1 1 d . . . H44 H 0.4878 0.5898 -0.4571 0.098 Uiso 1 1 calc R . . C45 C 0.5669(4) 0.6784(6) -0.3717(3) 0.0986(18) Uani 1 1 d . . . H45 H 0.5937 0.7505 -0.4005 0.118 Uiso 1 1 calc R . . C46 C 0.5906(3) 0.6669(5) -0.2978(2) 0.0788(13) Uani 1 1 d . . . H46 H 0.6369 0.7298 -0.2731 0.095 Uiso 1 1 calc R . . N4 N 0.4505(3) 0.3580(5) -0.2510(3) 0.0986(13) Uani 1 1 d D . . H3N H 0.397(2) 0.316(5) -0.2885(16) 0.118 Uiso 1 1 d D . . H4N H 0.434(3) 0.380(5) -0.2021(13) 0.118 Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0402(4) 0.0383(4) 0.0333(4) 0.0002(3) 0.0035(3) 0.0040(3) N1 0.0428(13) 0.0389(14) 0.0351(13) 0.0011(11) 0.0030(10) -0.0015(11) C1 0.0525(18) 0.0392(16) 0.0423(17) 0.0005(14) 0.0095(14) -0.0043(14) C11 0.060(2) 0.068(2) 0.069(2) -0.006(2) 0.0227(19) -0.0113(19) C12 0.078(2) 0.046(2) 0.048(2) 0.0073(16) 0.0057(18) -0.0054(18) C13 0.067(2) 0.0427(18) 0.0489(19) -0.0034(15) 0.0053(16) -0.0067(16) P2 0.0393(4) 0.0386(4) 0.0338(4) -0.0004(3) 0.0021(3) 0.0035(3) N2 0.0379(13) 0.0399(13) 0.0368(13) 0.0024(11) 0.0042(10) 0.0003(11) C2 0.0392(15) 0.0382(16) 0.0468(17) 0.0062(14) 0.0026(13) 0.0000(13) C21 0.065(2) 0.0396(18) 0.082(3) 0.0037(18) 0.007(2) 0.0039(17) C22 0.057(2) 0.061(2) 0.049(2) 0.0155(17) 0.0106(16) -0.0011(17) C23 0.0451(18) 0.058(2) 0.063(2) 0.0120(18) -0.0050(16) -0.0076(16) S1 0.0654(6) 0.0561(5) 0.0437(5) -0.0074(4) 0.0037(4) 0.0195(4) C31 0.0565(19) 0.0449(18) 0.0423(18) -0.0077(14) 0.0122(15) 0.0104(15) C32 0.0522(19) 0.054(2) 0.050(2) -0.0083(16) 0.0160(16) 0.0043(16) C33 0.073(2) 0.062(2) 0.050(2) 0.0046(18) 0.0224(18) 0.012(2) C34 0.063(2) 0.084(3) 0.047(2) -0.007(2) 0.0054(18) 0.020(2) C35 0.056(2) 0.077(3) 0.059(2) -0.016(2) 0.0083(18) -0.001(2) C36 0.062(2) 0.060(2) 0.050(2) -0.0069(17) 0.0099(17) 0.0006(18) N3 0.072(2) 0.102(3) 0.075(3) -0.001(2) 0.0196(19) -0.019(2) S2 0.0454(4) 0.0683(6) 0.0487(5) -0.0019(4) -0.0006(4) 0.0179(4) C41 0.0490(18) 0.057(2) 0.049(2) 0.0074(16) 0.0003(15) 0.0208(17) C42 0.065(2) 0.052(2) 0.094(3) 0.001(2) -0.010(2) 0.014(2) C43 0.090(3) 0.071(3) 0.107(4) -0.012(3) -0.015(3) 0.035(3) C44 0.099(4) 0.070(3) 0.072(3) -0.012(3) -0.003(3) 0.024(3) C45 0.123(4) 0.082(4) 0.097(4) 0.032(3) 0.040(3) 0.041(3) C46 0.089(3) 0.086(3) 0.060(3) 0.021(2) 0.008(2) 0.051(3) N4 0.070(2) 0.083(3) 0.141(4) 0.000(3) 0.008(3) -0.007(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 N2 1.704(3) . ? P1 N1 1.710(3) . ? P1 S1 2.1783(12) . ? P1 P2 2.5940(13) . ? N1 C1 1.484(4) . ? N1 P2 1.711(2) . ? C1 C13 1.521(5) . ? C1 C12 1.521(5) . ? C1 C11 1.542(5) . ? P2 N2 1.705(3) . ? P2 S2 2.1814(12) . ? N2 C2 1.481(4) . ? C2 C22 1.517(5) . ? C2 C23 1.521(4) . ? C2 C21 1.527(5) . ? S1 C31 1.782(4) . ? C31 C32 1.385(5) . ? C31 C36 1.401(5) . ? C32 N3 1.351(5) . ? C32 C33 1.416(5) . ? C33 C34 1.360(6) . ? C34 C35 1.364(6) . ? C35 C36 1.397(5) . ? S2 C41 1.769(4) . ? C41 C42 1.346(6) . ? C41 C46 1.462(6) . ? C42 N4 1.295(6) . ? C42 C43 1.502(7) . ? C43 C44 1.343(7) . ? C44 C45 1.361(7) . ? C45 C46 1.330(7) . ? 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 N2 P1 N1 81.07(12) . . ? N2 P1 S1 103.74(9) . . ? N1 P1 S1 106.87(9) . . ? N2 P1 P2 40.46(8) . . ? N1 P1 P2 40.70(8) . . ? S1 P1 P2 112.33(4) . . ? C1 N1 P1 130.0(2) . . ? C1 N1 P2 130.0(2) . . ? P1 N1 P2 98.62(13) . . ? N1 C1 C13 108.5(2) . . ? N1 C1 C12 108.9(3) . . ? C13 C1 C12 109.6(3) . . ? N1 C1 C11 109.0(3) . . ? C13 C1 C11 109.8(3) . . ? C12 C1 C11 110.9(3) . . ? N2 P2 N1 81.05(12) . . ? N2 P2 S2 105.16(9) . . ? N1 P2 S2 104.30(9) . . ? N2 P2 P1 40.45(9) . . ? N1 P2 P1 40.69(8) . . ? S2 P2 P1 111.56(5) . . ? C2 N2 P1 131.2(2) . . ? C2 N2 P2 129.6(2) . . ? P1 N2 P2 99.09(13) . . ? N2 C2 C22 108.8(3) . . ? N2 C2 C23 108.3(3) . . ? C22 C2 C23 109.0(3) . . ? N2 C2 C21 110.2(3) . . ? C22 C2 C21 110.0(3) . . ? C23 C2 C21 110.5(3) . . ? C31 S1 P1 99.28(11) . . ? C32 C31 C36 119.5(3) . . ? C32 C31 S1 120.2(3) . . ? C36 C31 S1 120.3(3) . . ? N3 C32 C31 120.5(3) . . ? N3 C32 C33 120.9(4) . . ? C31 C32 C33 118.6(3) . . ? C34 C33 C32 120.6(4) . . ? C33 C34 C35 121.6(4) . . ? C34 C35 C36 118.9(4) . . ? C35 C36 C31 120.7(4) . . ? C41 S2 P2 99.75(12) . . ? C42 C41 C46 120.7(4) . . ? C42 C41 S2 122.6(3) . . ? C46 C41 S2 116.6(3) . . ? N4 C42 C41 121.7(5) . . ? N4 C42 C43 119.9(5) . . ? C41 C42 C43 118.3(5) . . ? C44 C43 C42 114.4(5) . . ? C43 C44 C45 128.8(5) . . ? C46 C45 C44 116.8(5) . . ? C45 C46 C41 120.9(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 N2 P1 N1 C1 170.4(3) . . . . ? S1 P1 N1 C1 -87.8(3) . . . . ? P2 P1 N1 C1 167.3(3) . . . . ? N2 P1 N1 P2 3.09(12) . . . . ? S1 P1 N1 P2 104.84(10) . . . . ? P1 N1 C1 C13 -138.8(3) . . . . ? P2 N1 C1 C13 24.8(4) . . . . ? P1 N1 C1 C12 -19.5(4) . . . . ? P2 N1 C1 C12 144.0(2) . . . . ? P1 N1 C1 C11 101.6(3) . . . . ? P2 N1 C1 C11 -94.8(3) . . . . ? C1 N1 P2 N2 -170.4(3) . . . . ? P1 N1 P2 N2 -3.09(12) . . . . ? C1 N1 P2 S2 86.1(3) . . . . ? P1 N1 P2 S2 -106.57(10) . . . . ? C1 N1 P2 P1 -167.4(3) . . . . ? N1 P1 P2 N2 175.29(18) . . . . ? S1 P1 P2 N2 85.08(13) . . . . ? N2 P1 P2 N1 -175.29(18) . . . . ? S1 P1 P2 N1 -90.21(14) . . . . ? N2 P1 P2 S2 -88.27(13) . . . . ? N1 P1 P2 S2 87.01(13) . . . . ? S1 P1 P2 S2 -3.20(6) . . . . ? N1 P1 N2 C2 -178.5(3) . . . . ? S1 P1 N2 C2 76.2(3) . . . . ? P2 P1 N2 C2 -175.4(3) . . . . ? N1 P1 N2 P2 -3.11(12) . . . . ? S1 P1 N2 P2 -108.42(10) . . . . ? N1 P2 N2 C2 178.6(3) . . . . ? S2 P2 N2 C2 -78.9(3) . . . . ? P1 P2 N2 C2 175.5(3) . . . . ? N1 P2 N2 P1 3.11(12) . . . . ? S2 P2 N2 P1 105.61(10) . . . . ? P1 N2 C2 C22 145.7(2) . . . . ? P2 N2 C2 C22 -28.5(4) . . . . ? P1 N2 C2 C23 27.3(4) . . . . ? P2 N2 C2 C23 -146.9(2) . . . . ? P1 N2 C2 C21 -93.7(3) . . . . ? P2 N2 C2 C21 92.2(3) . . . . ? N2 P1 S1 C31 -145.83(15) . . . . ? N1 P1 S1 C31 129.49(15) . . . . ? P2 P1 S1 C31 172.44(12) . . . . ? P1 S1 C31 C32 -97.9(3) . . . . ? P1 S1 C31 C36 84.2(3) . . . . ? C36 C31 C32 N3 -175.3(3) . . . . ? S1 C31 C32 N3 6.8(5) . . . . ? C36 C31 C32 C33 3.2(5) . . . . ? S1 C31 C32 C33 -174.8(3) . . . . ? N3 C32 C33 C34 175.6(4) . . . . ? C31 C32 C33 C34 -2.9(5) . . . . ? C32 C33 C34 C35 0.1(6) . . . . ? C33 C34 C35 C36 2.3(6) . . . . ? C34 C35 C36 C31 -2.0(6) . . . . ? C32 C31 C36 C35 -0.8(5) . . . . ? S1 C31 C36 C35 177.1(3) . . . . ? N2 P2 S2 C41 129.69(16) . . . . ? N1 P2 S2 C41 -145.89(16) . . . . ? P1 P2 S2 C41 171.90(14) . . . . ? P2 S2 C41 C42 94.4(3) . . . . ? P2 S2 C41 C46 -88.3(3) . . . . ? C46 C41 C42 N4 173.0(4) . . . . ? S2 C41 C42 N4 -9.8(6) . . . . ? C46 C41 C42 C43 -2.8(5) . . . . ? S2 C41 C42 C43 174.4(3) . . . . ? N4 C42 C43 C44 -173.6(4) . . . . ? C41 C42 C43 C44 2.3(6) . . . . ? C42 C43 C44 C45 -1.8(7) . . . . ? C43 C44 C45 C46 1.9(8) . . . . ? C44 C45 C46 C41 -2.1(6) . . . . ? C42 C41 C46 C45 2.9(6) . . . . ? S2 C41 C46 C45 -174.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.083 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.084