Supplementary Material (ESI) for Dalton Transactions This journal is © The Royal Society of Chemistry 2004 data_global _publ_contact_author_email DSW1000@CUS.CAM.AC.UK _publ_contact_author_name 'Dr Dominic S Wright' _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_address ; Chemistry Department Cambridge University (U.K.) Lensfield Road Cambridge Cambridgeshire CB2 1EW UNITED KINGDOM ; _publ_section_title ; Steric Control in the Oligomerisation of Phosphazane Dimers; Towards New Phosphorus-Nitrogen Macrocycles ; loop_ _publ_author_name 'Dominic S. Wright' 'Emma L. Doyle' 'Felipe Garcia' 'Simon M. Humphrey' 'Richard A. Kowenicki' ; L.Riera ; 'Anthony Woods' data_compound6 _database_code_depnum_ccdc_archive 'CCDC 224368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'c24 h56 n6 o p4' _chemical_formula_sum 'C24 H56 N6 O P4' _chemical_formula_weight 568.63 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.8571(2) _cell_length_b 17.0620(4) _cell_length_c 20.2092(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.6518(14) _cell_angle_gamma 90.00 _cell_volume 3368.56(13) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 21837 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240 _exptl_absorpt_coefficient_mu 0.249 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 0.990 _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 17229 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.66 _diffrn_reflns_theta_max 27.43 _reflns_number_total 3795 _reflns_number_gt 2898 _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^)+(0.0311P)^2^+32.4345P] 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 3795 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1265 _refine_ls_R_factor_gt 0.0992 _refine_ls_wR_factor_ref 0.2268 _refine_ls_wR_factor_gt 0.2158 _refine_ls_goodness_of_fit_ref 1.211 _refine_ls_restrained_S_all 1.211 _refine_ls_shift/su_max 0.032 _refine_ls_shift/su_mean 0.005 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 0.03794(13) -0.04968(8) 0.32422(6) 0.0275(3) Uani 1 1 d . . . P2 P 0.20355(13) 0.04107(8) 0.40107(6) 0.0268(3) Uani 1 1 d . . . N1 N 0.0317(4) 0.0278(2) 0.3760(2) 0.0294(9) Uani 1 1 d . . . N2 N 0.2101(4) -0.0349(2) 0.3437(2) 0.0290(9) Uani 1 1 d . . . N3 N 0.2464(5) 0.1210(3) 0.3616(2) 0.0359(11) Uani 1 1 d . . . H3N H 0.204(7) 0.124(4) 0.320(3) 0.051(19) Uiso 1 1 d . . . O1 O 0.0000 -0.0069(3) 0.2500 0.0320(11) Uani 1 2 d S . . C1 C 0.3424(6) 0.1847(3) 0.3833(3) 0.0353(12) Uani 1 1 d . . . C2 C 0.4227(7) 0.1655(4) 0.4512(3) 0.0528(17) Uani 1 1 d . . . H2C H 0.4658 0.1139 0.4493 0.079 Uiso 1 1 calc R . . H2B H 0.3604 0.1649 0.4852 0.079 Uiso 1 1 calc R . . H2A H 0.4936 0.2053 0.4628 0.079 Uiso 1 1 calc R . . C3 C 0.4383(7) 0.1940(4) 0.3310(4) 0.0560(17) Uani 1 1 d . . . H3C H 0.4935 0.1464 0.3297 0.084 Uiso 1 1 calc R . . H3B H 0.4987 0.2390 0.3425 0.084 Uiso 1 1 calc R . . H3A H 0.3846 0.2026 0.2872 0.084 Uiso 1 1 calc R . . C4 C 0.2604(8) 0.2610(4) 0.3875(4) 0.0563(17) Uani 1 1 d . . . H4C H 0.2064 0.2716 0.3441 0.084 Uiso 1 1 calc R . . H4B H 0.3238 0.3046 0.3994 0.084 Uiso 1 1 calc R . . H4A H 0.1991 0.2554 0.4215 0.084 Uiso 1 1 calc R . . C5 C -0.0864(5) 0.0746(3) 0.3894(3) 0.0322(11) Uani 1 1 d . . . C6 C -0.1190(7) 0.1386(4) 0.3370(3) 0.0523(16) Uani 1 1 d . . . H6C H -0.1258 0.1154 0.2923 0.079 Uiso 1 1 calc R . . H6B H -0.0459 0.1780 0.3421 0.079 Uiso 1 1 calc R . . H6A H -0.2061 0.1635 0.3429 0.079 Uiso 1 1 calc R . . C7 C -0.2114(6) 0.0221(4) 0.3918(4) 0.0554(18) Uani 1 1 d . . . H7C H -0.2364 -0.0028 0.3482 0.083 Uiso 1 1 calc R . . H7B H -0.2882 0.0538 0.4027 0.083 Uiso 1 1 calc R . . H7A H -0.1896 -0.0184 0.4259 0.083 Uiso 1 1 calc R . . C8 C -0.0535(6) 0.1147(4) 0.4581(3) 0.0444(14) Uani 1 1 d . . . H8C H 0.0288 0.1470 0.4586 0.067 Uiso 1 1 calc R . . H8B H -0.0377 0.0747 0.4930 0.067 Uiso 1 1 calc R . . H8A H -0.1307 0.1479 0.4663 0.067 Uiso 1 1 calc R . . C9 C 0.3154(5) -0.0970(3) 0.3487(3) 0.0314(11) Uani 1 1 d . . . C10 C 0.3004(7) -0.1521(4) 0.4068(3) 0.0430(14) Uani 1 1 d . . . H10C H 0.3081 -0.1220 0.4484 0.065 Uiso 1 1 calc R . . H10B H 0.3726 -0.1919 0.4100 0.065 Uiso 1 1 calc R . . H10A H 0.2107 -0.1778 0.3992 0.065 Uiso 1 1 calc R . . C11 C 0.2972(7) -0.1424(4) 0.2834(3) 0.0467(15) Uani 1 1 d . . . H11C H 0.3081 -0.1068 0.2464 0.070 Uiso 1 1 calc R . . H11B H 0.2056 -0.1657 0.2763 0.070 Uiso 1 1 calc R . . H11A H 0.3662 -0.1840 0.2853 0.070 Uiso 1 1 calc R . . C12 C 0.4558(6) -0.0570(4) 0.3592(4) 0.0531(17) Uani 1 1 d . . . H12C H 0.4675 -0.0256 0.3198 0.080 Uiso 1 1 calc R . . H12B H 0.5277 -0.0970 0.3660 0.080 Uiso 1 1 calc R . . H12A H 0.4619 -0.0230 0.3985 0.080 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 0.0273(7) 0.0255(6) 0.0285(6) 0.0009(5) -0.0004(5) -0.0003(5) P2 0.0259(6) 0.0275(6) 0.0265(6) -0.0001(5) 0.0015(5) -0.0017(5) N1 0.023(2) 0.030(2) 0.035(2) -0.0020(17) 0.0023(17) 0.0017(17) N2 0.031(2) 0.025(2) 0.030(2) -0.0057(17) 0.0003(17) 0.0006(17) N3 0.044(3) 0.035(2) 0.026(2) 0.0036(18) -0.0064(19) -0.008(2) O1 0.038(3) 0.029(3) 0.027(2) 0.000 -0.003(2) 0.000 C1 0.039(3) 0.030(3) 0.036(3) 0.000(2) 0.004(2) -0.009(2) C2 0.061(4) 0.045(4) 0.046(4) -0.005(3) -0.016(3) -0.013(3) C3 0.047(4) 0.059(4) 0.067(4) 0.001(3) 0.025(3) -0.010(3) C4 0.070(5) 0.039(3) 0.060(4) 0.000(3) 0.011(3) 0.002(3) C5 0.022(3) 0.041(3) 0.035(3) -0.002(2) 0.012(2) 0.004(2) C6 0.052(4) 0.055(4) 0.049(4) 0.001(3) 0.003(3) 0.019(3) C7 0.032(3) 0.057(4) 0.078(5) -0.010(4) 0.013(3) -0.013(3) C8 0.046(4) 0.050(4) 0.040(3) -0.010(3) 0.017(3) 0.005(3) C9 0.032(3) 0.031(3) 0.031(3) -0.003(2) 0.001(2) 0.002(2) C10 0.047(3) 0.042(3) 0.038(3) 0.005(2) 0.000(3) 0.010(3) C11 0.057(4) 0.042(3) 0.041(3) -0.008(3) 0.004(3) 0.018(3) C12 0.030(3) 0.043(4) 0.087(5) -0.011(3) 0.011(3) 0.004(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 O1 1.665(2) . ? P1 N1 1.692(4) . ? P1 N2 1.709(4) . ? P1 P2 2.6075(18) . ? P2 N3 1.662(5) . ? P2 N1 1.717(4) . ? P2 N2 1.745(4) . ? N1 C5 1.466(6) . ? N2 C9 1.478(6) . ? N3 H3N 0.88(7) . ? N3 C1 1.469(7) . ? N3 H3N 0.88(7) . ? O1 P1 1.665(2) 2 ? C1 C3 1.516(8) . ? C1 C2 1.526(8) . ? C1 C4 1.541(8) . ? C2 H2C 0.9800 . ? C2 H2B 0.9800 . ? C2 H2A 0.9800 . ? C3 H3C 0.9800 . ? C3 H3B 0.9800 . ? C3 H3A 0.9800 . ? C4 H4C 0.9800 . ? C4 H4B 0.9800 . ? C4 H4A 0.9800 . ? C5 C6 1.525(8) . ? C5 C7 1.530(8) . ? C5 C8 1.543(7) . ? C6 H6C 0.9800 . ? C6 H6B 0.9800 . ? C6 H6A 0.9800 . ? C7 H7C 0.9800 . ? C7 H7B 0.9800 . ? C7 H7A 0.9800 . ? C8 H8C 0.9800 . ? C8 H8B 0.9800 . ? C8 H8A 0.9800 . ? C9 C11 1.520(7) . ? C9 C10 1.527(7) . ? C9 C12 1.532(8) . ? C10 H10C 0.9800 . ? C10 H10B 0.9800 . ? C10 H10A 0.9800 . ? C11 H11C 0.9800 . ? C11 H11B 0.9800 . ? C11 H11A 0.9800 . ? C12 H12C 0.9800 . ? C12 H12B 0.9800 . ? C12 H12A 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 N1 101.1(2) . . ? O1 P1 N2 103.88(16) . . ? N1 P1 N2 81.9(2) . . ? O1 P1 P2 108.89(15) . . ? N1 P1 P2 40.47(14) . . ? N2 P1 P2 41.51(14) . . ? N3 P2 N1 105.7(2) . . ? N3 P2 N2 104.9(2) . . ? N1 P2 N2 80.1(2) . . ? N3 P2 P1 112.37(17) . . ? N1 P2 P1 39.77(14) . . ? N2 P2 P1 40.46(14) . . ? C5 N1 P1 129.4(3) . . ? C5 N1 P2 130.5(4) . . ? P1 N1 P2 99.8(2) . . ? C9 N2 P1 125.2(3) . . ? C9 N2 P2 125.1(3) . . ? P1 N2 P2 98.0(2) . . ? H3N N3 C1 116(4) . . ? H3N N3 P2 112(4) . . ? C1 N3 P2 131.2(4) . . ? H3N N3 H3N 0(10) . . ? C1 N3 H3N 116(4) . . ? P2 N3 H3N 112(4) . . ? P1 O1 P1 128.0(3) 2 . ? N3 C1 C3 107.9(5) . . ? N3 C1 C2 110.2(4) . . ? C3 C1 C2 110.6(5) . . ? N3 C1 C4 108.7(5) . . ? C3 C1 C4 109.2(5) . . ? C2 C1 C4 110.2(5) . . ? C1 C2 H2C 109.5 . . ? C1 C2 H2B 109.5 . . ? H2C C2 H2B 109.5 . . ? C1 C2 H2A 109.5 . . ? H2C C2 H2A 109.5 . . ? H2B C2 H2A 109.5 . . ? C1 C3 H3C 109.5 . . ? C1 C3 H3B 109.5 . . ? H3C C3 H3B 109.5 . . ? C1 C3 H3A 109.5 . . ? H3C C3 H3A 109.5 . . ? H3B C3 H3A 109.5 . . ? C1 C4 H4C 109.5 . . ? C1 C4 H4B 109.5 . . ? H4C C4 H4B 109.5 . . ? C1 C4 H4A 109.5 . . ? H4C C4 H4A 109.5 . . ? H4B C4 H4A 109.5 . . ? N1 C5 C6 111.2(4) . . ? N1 C5 C7 110.4(5) . . ? C6 C5 C7 110.2(5) . . ? N1 C5 C8 109.3(4) . . ? C6 C5 C8 107.9(5) . . ? C7 C5 C8 107.8(5) . . ? C5 C6 H6C 109.5 . . ? C5 C6 H6B 109.5 . . ? H6C C6 H6B 109.5 . . ? C5 C6 H6A 109.5 . . ? H6C C6 H6A 109.5 . . ? H6B C6 H6A 109.5 . . ? C5 C7 H7C 109.5 . . ? C5 C7 H7B 109.5 . . ? H7C C7 H7B 109.5 . . ? C5 C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? C5 C8 H8C 109.5 . . ? C5 C8 H8B 109.5 . . ? H8C C8 H8B 109.5 . . ? C5 C8 H8A 109.5 . . ? H8C C8 H8A 109.5 . . ? H8B C8 H8A 109.5 . . ? N2 C9 C11 107.8(4) . . ? N2 C9 C10 110.8(4) . . ? C11 C9 C10 110.0(5) . . ? N2 C9 C12 107.6(4) . . ? C11 C9 C12 110.3(5) . . ? C10 C9 C12 110.2(5) . . ? C9 C10 H10C 109.5 . . ? C9 C10 H10B 109.5 . . ? H10C C10 H10B 109.5 . . ? C9 C10 H10A 109.5 . . ? H10C C10 H10A 109.5 . . ? H10B C10 H10A 109.5 . . ? C9 C11 H11C 109.5 . . ? C9 C11 H11B 109.5 . . ? H11C C11 H11B 109.5 . . ? C9 C11 H11A 109.5 . . ? H11C C11 H11A 109.5 . . ? H11B C11 H11A 109.5 . . ? C9 C12 H12C 109.5 . . ? C9 C12 H12B 109.5 . . ? H12C C12 H12B 109.5 . . ? C9 C12 H12A 109.5 . . ? H12C C12 H12A 109.5 . . ? H12B C12 H12A 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 O1 P1 P2 N3 -2.9(2) . . . . ? N1 P1 P2 N3 -87.9(3) . . . . ? N2 P1 P2 N3 86.9(3) . . . . ? O1 P1 P2 N1 85.0(2) . . . . ? N2 P1 P2 N1 174.7(3) . . . . ? O1 P1 P2 N2 -89.8(2) . . . . ? N1 P1 P2 N2 -174.7(3) . . . . ? O1 P1 N1 C5 68.0(4) . . . . ? N2 P1 N1 C5 170.7(5) . . . . ? P2 P1 N1 C5 174.2(6) . . . . ? O1 P1 N1 P2 -106.16(18) . . . . ? N2 P1 N1 P2 -3.5(2) . . . . ? N3 P2 N1 C5 -67.8(5) . . . . ? N2 P2 N1 C5 -170.6(5) . . . . ? P1 P2 N1 C5 -174.1(6) . . . . ? N3 P2 N1 P1 106.3(2) . . . . ? N2 P2 N1 P1 3.5(2) . . . . ? O1 P1 N2 C9 -112.9(4) . . . . ? N1 P1 N2 C9 147.6(4) . . . . ? P2 P1 N2 C9 144.1(5) . . . . ? O1 P1 N2 P2 102.9(2) . . . . ? N1 P1 N2 P2 3.4(2) . . . . ? N3 P2 N2 C9 108.6(4) . . . . ? N1 P2 N2 C9 -147.6(4) . . . . ? P1 P2 N2 C9 -144.2(5) . . . . ? N3 P2 N2 P1 -107.2(2) . . . . ? N1 P2 N2 P1 -3.4(2) . . . . ? N1 P2 N3 H3N -38(5) . . . . ? N2 P2 N3 H3N 45(5) . . . . ? P1 P2 N3 H3N 3(5) . . . . ? N1 P2 N3 C1 143.0(5) . . . . ? N2 P2 N3 C1 -133.3(5) . . . . ? P1 P2 N3 C1 -175.4(5) . . . . ? N1 P1 O1 P1 -168.87(16) . . . 2 ? N2 P1 O1 P1 106.86(16) . . . 2 ? P2 P1 O1 P1 149.91(8) . . . 2 ? H3N N3 C1 C3 -51(5) . . . . ? P2 N3 C1 C3 127.8(5) . . . . ? H3N N3 C1 C2 -172(5) . . . . ? P2 N3 C1 C2 7.0(8) . . . . ? H3N N3 C1 C4 68(5) . . . . ? P2 N3 C1 C4 -113.8(6) . . . . ? P1 N1 C5 C6 -83.8(6) . . . . ? P2 N1 C5 C6 88.7(6) . . . . ? P1 N1 C5 C7 38.9(7) . . . . ? P2 N1 C5 C7 -148.7(5) . . . . ? P1 N1 C5 C8 157.3(4) . . . . ? P2 N1 C5 C8 -30.3(7) . . . . ? P1 N2 C9 C11 54.6(6) . . . . ? P2 N2 C9 C11 -170.6(4) . . . . ? P1 N2 C9 C10 -65.8(5) . . . . ? P2 N2 C9 C10 69.1(5) . . . . ? P1 N2 C9 C12 173.6(4) . . . . ? P2 N2 C9 C12 -51.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.635 _refine_diff_density_min -0.422 _refine_diff_density_rms 0.096 data_compound5 _database_code_depnum_ccdc_archive 'CCDC 224369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H29 N3 O P2' _chemical_formula_sum 'C12 H29 N3 O P2' _chemical_formula_weight 293.32 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 monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 18.424(4) _cell_length_b 8.3179(17) _cell_length_c 23.430(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.70(3) _cell_angle_gamma 90.00 _cell_volume 3336.3(12) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 22343 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.256 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.908 _exptl_absorpt_correction_T_max 1.000 _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 13812 _diffrn_reflns_av_R_equivalents 0.1184 _diffrn_reflns_av_sigmaI/netI 0.0970 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 25.04 _reflns_number_total 2919 _reflns_number_gt 1797 _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^)+(0.0297P)^2^+8.2737P] 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 2919 _refine_ls_number_parameters 180 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_gt 0.0576 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1019 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 0.23956(5) 0.28185(13) 0.28792(4) 0.0295(3) Uani 1 1 d . . . P2 P 0.32372(5) 0.41380(13) 0.38954(4) 0.0298(3) Uani 1 1 d . . . O1 O 0.19189(13) 0.3222(3) 0.22397(10) 0.0381(7) Uani 1 1 d . . . N1 N 0.32997(15) 0.3489(4) 0.32041(12) 0.0293(7) Uani 1 1 d . . . N2 N 0.33336(17) 0.6096(4) 0.38734(14) 0.0320(8) Uani 1 1 d . . . N3 N 0.22495(15) 0.3674(4) 0.34610(12) 0.0295(8) Uani 1 1 d . . . C10 C 0.4008(2) 0.3047(5) 0.30777(16) 0.0320(9) Uani 1 1 d . . . C11 C 0.4381(2) 0.1554(5) 0.34374(19) 0.0489(12) Uani 1 1 d . . . H11A H 0.4493 0.1735 0.3875 0.073 Uiso 1 1 calc R . . H11B H 0.4868 0.1320 0.3376 0.073 Uiso 1 1 calc R . . H11C H 0.4022 0.0642 0.3293 0.073 Uiso 1 1 calc R . . C12 C 0.4573(2) 0.4472(5) 0.32667(19) 0.0468(11) Uani 1 1 d . . . H12A H 0.4304 0.5450 0.3063 0.070 Uiso 1 1 calc R . . H12B H 0.5019 0.4264 0.3145 0.070 Uiso 1 1 calc R . . H12C H 0.4759 0.4614 0.3713 0.070 Uiso 1 1 calc R . . C13 C 0.3765(2) 0.2746(6) 0.23930(17) 0.0452(11) Uani 1 1 d . . . H13A H 0.3411 0.1821 0.2275 0.068 Uiso 1 1 calc R . . H13B H 0.4230 0.2523 0.2297 0.068 Uiso 1 1 calc R . . H13C H 0.3499 0.3699 0.2166 0.068 Uiso 1 1 calc R . . C20 C 0.3716(2) 0.7233(5) 0.43837(16) 0.0337(9) Uani 1 1 d . . . C21 C 0.4510(2) 0.7714(5) 0.43718(19) 0.0495(12) Uani 1 1 d . . . H21A H 0.4859 0.6779 0.4474 0.074 Uiso 1 1 calc R . . H21B H 0.4738 0.8568 0.4673 0.074 Uiso 1 1 calc R . . H21C H 0.4445 0.8104 0.3961 0.074 Uiso 1 1 calc R . . C22 C 0.3195(2) 0.8704(5) 0.42795(18) 0.0465(11) Uani 1 1 d . . . H22A H 0.3114 0.9166 0.3876 0.070 Uiso 1 1 calc R . . H22B H 0.3445 0.9503 0.4599 0.070 Uiso 1 1 calc R . . H22C H 0.2690 0.8392 0.4296 0.070 Uiso 1 1 calc R . . C23 C 0.3821(3) 0.6458(5) 0.49986(16) 0.0499(12) Uani 1 1 d . . . H23A H 0.3309 0.6148 0.5002 0.075 Uiso 1 1 calc R . . H23B H 0.4069 0.7227 0.5331 0.075 Uiso 1 1 calc R . . H23C H 0.4151 0.5502 0.5059 0.075 Uiso 1 1 calc R . . C30 C 0.16097(19) 0.3399(5) 0.36970(15) 0.0324(9) Uani 1 1 d . . . C31 C 0.1758(2) 0.1868(6) 0.40824(19) 0.0514(12) Uani 1 1 d . . . H31A H 0.1766 0.0942 0.3826 0.077 Uiso 1 1 calc R . . H31B H 0.1341 0.1727 0.4243 0.077 Uiso 1 1 calc R . . H31C H 0.2262 0.1952 0.4425 0.077 Uiso 1 1 calc R . . C32 C 0.0840(2) 0.3245(5) 0.31432(17) 0.0427(11) Uani 1 1 d . . . H32A H 0.0762 0.4205 0.2885 0.064 Uiso 1 1 calc R . . H32B H 0.0406 0.3142 0.3287 0.064 Uiso 1 1 calc R . . H32C H 0.0859 0.2291 0.2904 0.064 Uiso 1 1 calc R . . C33 C 0.1578(2) 0.4845(6) 0.40820(17) 0.0445(11) Uani 1 1 d . . . H33A H 0.2064 0.4912 0.4443 0.067 Uiso 1 1 calc R . . H33B H 0.1135 0.4731 0.4216 0.067 Uiso 1 1 calc R . . H33C H 0.1513 0.5825 0.3836 0.067 Uiso 1 1 calc R . . H1P H 0.2426(18) 0.119(4) 0.2932(13) 0.032(9) Uiso 1 1 d . . . H2N H 0.3208(19) 0.656(4) 0.3527(15) 0.025(10) 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 0.0274(5) 0.0315(6) 0.0299(5) -0.0034(5) 0.0110(4) -0.0008(5) P2 0.0266(5) 0.0333(6) 0.0277(5) -0.0010(4) 0.0079(4) 0.0016(5) O1 0.0341(14) 0.051(2) 0.0269(14) -0.0039(12) 0.0084(11) 0.0022(13) N1 0.0229(16) 0.034(2) 0.0303(16) -0.0035(14) 0.0084(12) 0.0006(13) N2 0.0381(18) 0.033(2) 0.0221(17) 0.0028(15) 0.0078(14) 0.0021(15) N3 0.0259(16) 0.037(2) 0.0261(16) -0.0036(14) 0.0102(12) 0.0000(14) C10 0.028(2) 0.034(3) 0.038(2) -0.0037(18) 0.0165(16) 0.0031(17) C11 0.039(2) 0.048(3) 0.062(3) 0.002(2) 0.021(2) 0.011(2) C12 0.038(2) 0.046(3) 0.064(3) -0.014(2) 0.028(2) -0.006(2) C13 0.039(2) 0.056(3) 0.047(2) -0.007(2) 0.0235(19) 0.001(2) C20 0.035(2) 0.033(2) 0.031(2) -0.0053(18) 0.0103(16) 0.0023(19) C21 0.042(2) 0.045(3) 0.057(3) -0.008(2) 0.011(2) -0.008(2) C22 0.054(3) 0.040(3) 0.042(2) -0.006(2) 0.015(2) 0.009(2) C23 0.064(3) 0.050(3) 0.025(2) -0.0045(19) 0.0048(19) -0.002(2) C30 0.027(2) 0.040(3) 0.034(2) 0.0011(18) 0.0151(16) 0.0018(17) C31 0.048(3) 0.055(3) 0.059(3) 0.015(2) 0.029(2) 0.005(2) C32 0.031(2) 0.058(3) 0.041(2) -0.004(2) 0.0159(17) -0.004(2) C33 0.033(2) 0.061(3) 0.043(2) -0.009(2) 0.0183(18) 0.000(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 H1P 1.36(3) . ? P1 O1 1.468(2) . ? P1 N3 1.646(3) . ? P1 N1 1.651(3) . ? P1 P2 2.5591(15) . ? P2 N2 1.641(3) . ? P2 N1 1.751(3) . ? P2 N3 1.768(3) . ? N1 C10 1.486(4) . ? N2 H2N 0.85(3) . ? N2 C20 1.483(5) . ? N3 C30 1.493(4) . ? C10 C13 1.519(5) . ? C10 C11 1.515(5) . ? C10 C12 1.532(5) . ? C20 C22 1.518(5) . ? C20 C21 1.527(5) . ? C20 C23 1.524(5) . ? C30 C33 1.518(5) . ? C30 C31 1.526(5) . ? C30 C32 1.534(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H1P P1 O1 108.0(12) . . ? H1P P1 N3 111.7(13) . . ? O1 P1 N3 121.80(15) . . ? H1P P1 N1 107.1(13) . . ? O1 P1 N1 120.94(16) . . ? N3 P1 N1 85.31(14) . . ? H1P P1 P2 110.6(12) . . ? O1 P1 P2 141.21(12) . . ? N3 P1 P2 43.30(10) . . ? N1 P1 P2 42.73(10) . . ? N2 P2 N1 103.42(16) . . ? N2 P2 N3 107.38(15) . . ? N1 P2 N3 78.81(13) . . ? N2 P2 P1 115.58(12) . . ? N1 P2 P1 39.78(9) . . ? N3 P2 P1 39.66(9) . . ? C10 N1 P1 129.4(2) . . ? C10 N1 P2 128.5(2) . . ? P1 N1 P2 97.49(15) . . ? H2N N2 C20 111(2) . . ? H2N N2 P2 119(2) . . ? C20 N2 P2 129.2(3) . . ? C30 N3 P1 129.3(2) . . ? C30 N3 P2 127.3(2) . . ? P1 N3 P2 97.04(14) . . ? N1 C10 C13 108.3(3) . . ? N1 C10 C11 110.0(3) . . ? C13 C10 C11 110.4(3) . . ? N1 C10 C12 107.7(3) . . ? C13 C10 C12 109.6(3) . . ? C11 C10 C12 110.7(3) . . ? N2 C20 C22 107.5(3) . . ? N2 C20 C21 109.0(3) . . ? C22 C20 C21 109.8(3) . . ? N2 C20 C23 110.4(3) . . ? C22 C20 C23 110.1(3) . . ? C21 C20 C23 110.0(3) . . ? N3 C30 C33 107.9(3) . . ? N3 C30 C31 110.7(3) . . ? C33 C30 C31 110.3(3) . . ? N3 C30 C32 108.0(3) . . ? C33 C30 C32 110.0(3) . . ? C31 C30 C32 109.8(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.291 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.061 data_compound3 _database_code_depnum_ccdc_archive 'CCDC 224370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H38 N4 O3 P4' _chemical_formula_sum 'C16 H38 N4 O3 P4' _chemical_formula_weight 458.38 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 10.5902(4) _cell_length_b 10.6397(3) _cell_length_c 11.8618(5) _cell_angle_alpha 92.8210(10) _cell_angle_beta 91.2300(10) _cell_angle_gamma 107.1730(10) _cell_volume 1274.50(8) _cell_formula_units_Z 2 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9128 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.194 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 0.318 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.898 _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 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_detector_area_resol_mean 9 _diffrn_radiation_monochromator 'horizonally mounted graphite crystal' _diffrn_measurement_method CCD _diffrn_reflns_number 12815 _diffrn_reflns_av_R_equivalents 0.0588 _diffrn_reflns_av_sigmaI/netI 0.0836 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5773 _reflns_number_gt 3655 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinowski & Minor 1997) ; _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0176P)^2^+1.6166P] 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 5773 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1140 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1361 _refine_ls_wR_factor_gt 0.1146 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.003 _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 O1 O 0.1449(2) -0.3407(2) -1.2417(2) 0.0474(6) Uani 1 1 d . . . P1 P 0.14343(8) -0.43874(7) -1.13864(8) 0.0370(2) Uani 1 1 d . . . P2 P 0.38086(9) -0.40647(9) -1.07931(8) 0.0471(2) Uani 1 1 d . . . P3 P 0.04256(8) -0.35561(7) -1.35126(7) 0.0367(2) Uani 1 1 d . . . P4 P 0.04946(11) -0.12560(9) -1.39608(9) 0.0580(3) Uani 1 1 d . . . N1 N 0.2646(2) -0.3363(2) -1.0503(2) 0.0383(6) Uani 1 1 d . . . N2 N 0.2687(3) -0.5054(2) -1.1697(2) 0.0416(7) Uani 1 1 d . . . N3 N 0.1335(3) -0.2303(2) -1.4277(2) 0.0466(7) Uani 1 1 d . . . N4 N -0.0405(3) -0.2433(2) -1.3185(2) 0.0441(7) Uani 1 1 d . . . O2 O 0.5112(2) -0.3302(3) -1.1142(2) 0.0686(8) Uani 1 1 d . . . O4 O 0.1179(3) 0.0078(2) -1.3500(3) 0.0840(10) Uani 1 1 d . . . C1 C 0.2702(3) -0.2107(3) -0.9872(3) 0.0443(8) Uani 1 1 d . . . C2 C 0.2582(4) -0.6389(3) -1.2208(3) 0.0475(9) Uani 1 1 d . . . C3 C 0.2622(4) -0.2105(4) -1.4806(3) 0.0619(11) Uani 1 1 d . . . C4 C -0.1734(4) -0.2641(4) -1.2717(3) 0.0516(9) Uani 1 1 d . . . C11 C 0.3634(4) -0.1952(4) -0.8842(3) 0.0647(11) Uani 1 1 d . . . H11A H 0.3276 -0.2674 -0.8347 0.097 Uiso 1 1 calc R . . H11B H 0.3719 -0.1109 -0.8430 0.097 Uiso 1 1 calc R . . H11C H 0.4505 -0.1975 -0.9088 0.097 Uiso 1 1 calc R . . C12 C 0.1324(4) -0.2196(4) -0.9512(4) 0.0811(15) Uani 1 1 d . . . H12A H 0.0738 -0.2298 -1.0182 0.122 Uiso 1 1 calc R . . H12B H 0.1339 -0.1390 -0.9068 0.122 Uiso 1 1 calc R . . H12C H 0.1000 -0.2958 -0.9051 0.122 Uiso 1 1 calc R . . C13 C 0.3229(4) -0.0958(3) -1.0621(4) 0.0649(11) Uani 1 1 d . . . H13A H 0.4098 -0.0962 -1.0887 0.097 Uiso 1 1 calc R . . H13B H 0.3314 -0.0128 -1.0186 0.097 Uiso 1 1 calc R . . H13C H 0.2616 -0.1044 -1.1270 0.097 Uiso 1 1 calc R . . C21 C 0.3850(4) -0.6326(4) -1.2792(4) 0.0718(12) Uani 1 1 d . . . H21A H 0.3973 -0.5701 -1.3389 0.108 Uiso 1 1 calc R . . H21B H 0.3802 -0.7201 -1.3124 0.108 Uiso 1 1 calc R . . H21C H 0.4596 -0.6034 -1.2242 0.108 Uiso 1 1 calc R . . C22 C 0.2351(4) -0.7396(3) -1.1296(3) 0.0598(10) Uani 1 1 d . . . H22A H 0.3103 -0.7149 -1.0750 0.090 Uiso 1 1 calc R . . H22B H 0.2263 -0.8272 -1.1648 0.090 Uiso 1 1 calc R . . H22C H 0.1540 -0.7411 -1.0907 0.090 Uiso 1 1 calc R . . C23 C 0.1410(4) -0.6763(3) -1.3060(3) 0.0607(11) Uani 1 1 d . . . H23A H 0.0598 -0.6790 -1.2669 0.091 Uiso 1 1 calc R . . H23B H 0.1326 -0.7631 -1.3426 0.091 Uiso 1 1 calc R . . H23C H 0.1555 -0.6107 -1.3633 0.091 Uiso 1 1 calc R . . C31 C 0.2759(5) -0.3438(5) -1.5178(6) 0.113(2) Uani 1 1 d . . . H31A H 0.2763 -0.3952 -1.4515 0.170 Uiso 1 1 calc R . . H31B H 0.3589 -0.3319 -1.5568 0.170 Uiso 1 1 calc R . . H31C H 0.2014 -0.3908 -1.5692 0.170 Uiso 1 1 calc R . . C32 C 0.2643(6) -0.1254(6) -1.5818(4) 0.115(2) Uani 1 1 d . . . H32A H 0.1888 -0.1683 -1.6335 0.172 Uiso 1 1 calc R . . H32B H 0.3467 -0.1149 -1.6214 0.172 Uiso 1 1 calc R . . H32C H 0.2588 -0.0386 -1.5550 0.172 Uiso 1 1 calc R . . C33 C 0.3744(4) -0.1378(5) -1.3971(4) 0.0807(14) Uani 1 1 d . . . H33A H 0.3631 -0.0527 -1.3725 0.121 Uiso 1 1 calc R . . H33B H 0.4592 -0.1235 -1.4337 0.121 Uiso 1 1 calc R . . H33C H 0.3730 -0.1906 -1.3315 0.121 Uiso 1 1 calc R . . C41 C -0.2786(4) -0.2904(5) -1.3678(4) 0.0801(14) Uani 1 1 d . . . H41A H -0.2589 -0.2151 -1.4158 0.120 Uiso 1 1 calc R . . H41B H -0.3659 -0.3031 -1.3360 0.120 Uiso 1 1 calc R . . H41C H -0.2784 -0.3699 -1.4132 0.120 Uiso 1 1 calc R . . C42 C -0.1724(5) -0.1406(4) -1.2003(4) 0.0848(15) Uani 1 1 d . . . H42A H -0.1063 -0.1258 -1.1381 0.127 Uiso 1 1 calc R . . H42B H -0.2600 -0.1520 -1.1696 0.127 Uiso 1 1 calc R . . H42C H -0.1503 -0.0645 -1.2474 0.127 Uiso 1 1 calc R . . C43 C -0.2020(4) -0.3819(4) -1.1985(4) 0.0639(11) Uani 1 1 d . . . H43A H -0.2091 -0.4619 -1.2459 0.096 Uiso 1 1 calc R . . H43B H -0.2854 -0.3912 -1.1607 0.096 Uiso 1 1 calc R . . H43C H -0.1300 -0.3685 -1.1416 0.096 Uiso 1 1 calc R . . H2 H 0.3917 -0.4717 -0.9837 0.039(8) Uiso 1 1 d R . . H4 H -0.0209 -0.1241 -1.4886 0.080(12) Uiso 1 1 d 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 O1 0.0429(13) 0.0370(11) 0.0601(16) 0.0130(10) -0.0114(11) 0.0080(10) P1 0.0333(4) 0.0306(4) 0.0480(5) 0.0040(3) 0.0001(4) 0.0109(3) P2 0.0402(5) 0.0574(5) 0.0486(6) -0.0061(4) -0.0082(4) 0.0240(4) P3 0.0363(4) 0.0300(4) 0.0449(5) 0.0022(3) 0.0005(4) 0.0115(3) P4 0.0832(8) 0.0346(5) 0.0571(7) 0.0072(4) -0.0168(5) 0.0195(5) N1 0.0333(14) 0.0377(13) 0.0447(17) -0.0013(12) 0.0001(12) 0.0126(11) N2 0.0416(15) 0.0441(14) 0.0460(17) -0.0050(12) -0.0050(13) 0.0249(12) N3 0.0570(18) 0.0336(14) 0.0445(17) 0.0080(12) 0.0022(14) 0.0050(13) N4 0.0534(17) 0.0359(14) 0.0499(18) 0.0032(12) -0.0030(14) 0.0243(13) O2 0.0348(14) 0.092(2) 0.077(2) -0.0192(16) -0.0009(13) 0.0195(13) O4 0.126(3) 0.0297(13) 0.092(2) -0.0004(13) -0.024(2) 0.0192(15) C1 0.0442(19) 0.0352(16) 0.051(2) -0.0053(15) 0.0054(16) 0.0089(14) C2 0.061(2) 0.0444(18) 0.045(2) -0.0040(15) -0.0057(17) 0.0284(17) C3 0.061(3) 0.057(2) 0.050(2) 0.0013(18) 0.0136(19) -0.0104(19) C4 0.049(2) 0.064(2) 0.052(2) -0.0114(18) -0.0072(17) 0.0360(18) C11 0.083(3) 0.057(2) 0.046(2) -0.0072(18) -0.004(2) 0.011(2) C12 0.058(3) 0.055(2) 0.123(4) -0.033(2) 0.030(3) 0.011(2) C13 0.077(3) 0.0382(19) 0.070(3) 0.0032(18) -0.011(2) 0.0029(18) C21 0.082(3) 0.071(3) 0.075(3) -0.003(2) 0.016(2) 0.042(2) C22 0.075(3) 0.049(2) 0.064(3) 0.0053(18) -0.006(2) 0.0307(19) C23 0.084(3) 0.0430(19) 0.060(3) -0.0140(17) -0.022(2) 0.0304(19) C31 0.084(4) 0.074(3) 0.161(6) -0.037(3) 0.067(4) -0.006(3) C32 0.109(4) 0.137(5) 0.059(3) 0.032(3) 0.005(3) -0.027(4) C33 0.059(3) 0.092(3) 0.072(3) 0.006(3) 0.003(2) -0.007(2) C41 0.071(3) 0.108(4) 0.073(3) -0.013(3) -0.019(2) 0.050(3) C42 0.096(4) 0.081(3) 0.092(4) -0.029(3) 0.000(3) 0.055(3) C43 0.049(2) 0.080(3) 0.070(3) 0.004(2) 0.010(2) 0.029(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 O1 P1 1.643(2) . ? O1 P3 1.645(2) . ? P1 N1 1.714(3) . ? P1 N2 1.718(3) . ? P1 P2 2.5151(12) . ? P2 O2 1.460(3) . ? P2 N1 1.651(3) . ? P2 N2 1.663(3) . ? P2 H2 1.3782 . ? P3 N3 1.710(3) . ? P3 N4 1.716(3) . ? P3 P4 2.5102(11) . ? P4 O4 1.462(3) . ? P4 N3 1.653(3) . ? P4 N4 1.664(3) . ? P4 H4 1.3171 . ? N1 C1 1.484(4) . ? N2 C2 1.488(4) . ? N3 C3 1.475(5) . ? N4 C4 1.483(4) . ? C1 C12 1.506(5) . ? C1 C13 1.523(5) . ? C1 C11 1.525(5) . ? C2 C21 1.510(5) . ? C2 C23 1.528(5) . ? C2 C22 1.533(5) . ? C3 C31 1.513(6) . ? C3 C33 1.524(5) . ? C3 C32 1.535(6) . ? C4 C43 1.521(5) . ? C4 C42 1.526(5) . ? C4 C41 1.533(5) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C41 H41A 0.9800 . ? C41 H41B 0.9800 . ? C41 H41C 0.9800 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C43 H43A 0.9800 . ? C43 H43B 0.9800 . ? C43 H43C 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 P1 O1 P3 130.90(13) . . ? O1 P1 N1 99.80(12) . . ? O1 P1 N2 103.58(13) . . ? N1 P1 N2 81.76(12) . . ? O1 P1 P2 106.70(9) . . ? N1 P1 P2 40.69(9) . . ? N2 P1 P2 41.09(9) . . ? O2 P2 N1 121.65(15) . . ? O2 P2 N2 122.22(16) . . ? N1 P2 N2 85.32(13) . . ? O2 P2 P1 137.24(12) . . ? N1 P2 P1 42.58(9) . . ? N2 P2 P1 42.77(9) . . ? O2 P2 H2 110.7 . . ? N1 P2 H2 103.9 . . ? N2 P2 H2 109.7 . . ? P1 P2 H2 111.9 . . ? O1 P3 N3 99.79(13) . . ? O1 P3 N4 103.61(13) . . ? N3 P3 N4 82.10(14) . . ? O1 P3 P4 106.21(8) . . ? N3 P3 P4 40.85(10) . . ? N4 P3 P4 41.26(10) . . ? O4 P4 N3 120.43(18) . . ? O4 P4 N4 123.16(18) . . ? N3 P4 N4 85.42(13) . . ? O4 P4 P3 136.45(12) . . ? N3 P4 P3 42.60(10) . . ? N4 P4 P3 42.83(9) . . ? O4 P4 H4 111.5 . . ? N3 P4 H4 105.0 . . ? N4 P4 H4 107.7 . . ? P3 P4 H4 111.9 . . ? C1 N1 P2 131.5(2) . . ? C1 N1 P1 130.7(2) . . ? P2 N1 P1 96.72(13) . . ? C2 N2 P2 130.9(2) . . ? C2 N2 P1 128.3(2) . . ? P2 N2 P1 96.14(14) . . ? C3 N3 P4 131.0(2) . . ? C3 N3 P3 131.0(2) . . ? P4 N3 P3 96.55(16) . . ? C4 N4 P4 131.3(2) . . ? C4 N4 P3 129.6(2) . . ? P4 N4 P3 95.92(16) . . ? N1 C1 C12 107.8(3) . . ? N1 C1 C13 109.8(3) . . ? C12 C1 C13 111.2(3) . . ? N1 C1 C11 107.9(3) . . ? C12 C1 C11 110.4(4) . . ? C13 C1 C11 109.6(3) . . ? N2 C2 C21 108.4(3) . . ? N2 C2 C23 107.5(2) . . ? C21 C2 C23 110.5(3) . . ? N2 C2 C22 110.5(3) . . ? C21 C2 C22 110.1(3) . . ? C23 C2 C22 109.8(3) . . ? N3 C3 C31 108.7(3) . . ? N3 C3 C33 110.2(3) . . ? C31 C3 C33 110.4(4) . . ? N3 C3 C32 107.6(4) . . ? C31 C3 C32 111.2(4) . . ? C33 C3 C32 108.8(3) . . ? N4 C4 C43 108.6(3) . . ? N4 C4 C42 108.3(3) . . ? C43 C4 C42 110.0(4) . . ? N4 C4 C41 110.2(3) . . ? C43 C4 C41 109.7(3) . . ? C42 C4 C41 110.1(3) . . ? C1 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C1 C12 H12A 109.5 . . ? C1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 C13 H13A 109.5 . . ? C1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2 C21 H21A 109.5 . . ? C2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C2 C22 H22A 109.5 . . ? C2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C2 C23 H23A 109.5 . . ? C2 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C2 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C3 C31 H31A 109.5 . . ? C3 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C3 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C3 C32 H32A 109.5 . . ? C3 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C3 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C3 C33 H33A 109.5 . . ? C3 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C3 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C4 C41 H41A 109.5 . . ? C4 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C4 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C4 C42 H42A 109.5 . . ? C4 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C4 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? C4 C43 H43A 109.5 . . ? C4 C43 H43B 109.5 . . ? H43A C43 H43B 109.5 . . ? C4 C43 H43C 109.5 . . ? H43A C43 H43C 109.5 . . ? H43B C43 H43C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.282 _refine_diff_density_min -0.416 _refine_diff_density_rms 0.074