data_04src0238 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H24 Cl3 N4 O5 P3' _chemical_formula_weight 491.60 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' 'Cl' 'Cl' 0.1484 0.1585 '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 _symmetry_spacE_group_name_hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.342(3) _cell_length_b 14.132(3) _cell_length_c 12.611(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.835(18) _cell_angle_gamma 90.00 _cell_volume 2199.3(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 46150 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.485 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.663 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.7327 _exptl_absorpt_correction_T_max 0.8011 _exptl_absorpt_process_details 'SORTAV (R.H.Blessing, 1995, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method '\F & \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29053 _diffrn_reflns_av_R_equivalents 0.0720 _diffrn_reflns_av_sigmaI/netI 0.0389 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5047 _reflns_number_gt 3746 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0689P)^2^+1.6755P] 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 0.0035(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 5047 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0822 _refine_ls_R_factor_gt 0.0591 _refine_ls_wR_factor_ref 0.1592 _refine_ls_wR_factor_gt 0.1452 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 C1 C 0.8986(3) 0.0233(2) 1.1462(3) 0.0653(9) Uani 1 1 d . . . H1A H 0.9006 0.0074 1.0698 0.078 Uiso 1 1 calc R . . H1B H 0.8553 -0.0255 1.1827 0.078 Uiso 1 1 calc R . . C2 C 1.0102(3) 0.0253(3) 1.1912(3) 0.0730(10) Uani 1 1 d . . . H2A H 1.0099 0.0550 1.2623 0.088 Uiso 1 1 calc R . . H2B H 1.0380 -0.0401 1.1990 0.088 Uiso 1 1 calc R . . C3 C 1.1858(4) 0.0787(3) 1.1627(4) 0.0836(12) Uani 1 1 d . . . H3A H 1.2118 0.0132 1.1742 0.100 Uiso 1 1 calc R . . H3B H 1.1889 0.1123 1.2316 0.100 Uiso 1 1 calc R . . C4 C 1.2565(4) 0.1274(4) 1.0859(4) 0.0967(15) Uani 1 1 d . . . H4A H 1.3334 0.1191 1.1074 0.116 Uiso 1 1 calc R . . H4B H 1.2462 0.0991 1.0146 0.116 Uiso 1 1 calc R . . C5 C 1.2900(4) 0.2831(5) 1.0101(4) 0.1038(17) Uani 1 1 d . . . H5A H 1.3653 0.2593 1.0066 0.125 Uiso 1 1 calc R . . H5B H 1.2931 0.3482 1.0388 0.125 Uiso 1 1 calc R . . C6 C 1.2453(4) 0.2866(5) 0.9044(4) 0.1039(17) Uani 1 1 d . . . H6A H 1.2921 0.3259 0.8589 0.125 Uiso 1 1 calc R . . H6B H 1.2423 0.2220 0.8741 0.125 Uiso 1 1 calc R . . C7 C 1.0632(4) 0.2647(5) 0.8650(5) 0.120(2) Uani 1 1 d . . . H7A H 1.0738 0.2595 0.7876 0.144 Uiso 1 1 calc R . . H7B H 1.0751 0.2012 0.8962 0.144 Uiso 1 1 calc R . . C8 C 0.9632(4) 0.2903(4) 0.8820(6) 0.138(3) Uani 1 1 d . . . H8A H 0.9544 0.3571 0.8601 0.166 Uiso 1 1 calc R . . H8B H 0.9498 0.2868 0.9591 0.166 Uiso 1 1 calc R . . C9 C 0.5982(3) 0.1264(2) 0.7847(3) 0.0570(8) Uani 1 1 d . . . H9 H 0.5973 0.0866 0.8503 0.068 Uiso 1 1 calc R . . C10 C 0.5063(3) 0.1967(4) 0.7903(5) 0.1022(16) Uani 1 1 d . . . H10A H 0.5165 0.2372 0.8527 0.153 Uiso 1 1 calc R . . H10B H 0.4374 0.1626 0.7956 0.153 Uiso 1 1 calc R . . H10C H 0.5053 0.2358 0.7261 0.153 Uiso 1 1 calc R . . C11 C 0.5852(3) 0.0622(3) 0.6902(3) 0.0783(11) Uani 1 1 d . . . H11A H 0.6445 0.0160 0.6899 0.117 Uiso 1 1 calc R . . H11B H 0.5870 0.0999 0.6250 0.117 Uiso 1 1 calc R . . H11C H 0.5158 0.0289 0.6941 0.117 Uiso 1 1 calc R . . N1 N 0.7255(3) 0.2534(2) 1.1278(2) 0.0676(8) Uani 1 1 d . . . N2 N 0.7788(2) 0.13485(18) 0.96777(19) 0.0569(7) Uani 1 1 d . . . N3 N 0.7262(2) 0.31408(19) 0.9245(2) 0.0617(7) Uani 1 1 d . . . N4 N 0.7034(2) 0.1737(2) 0.7796(2) 0.0517(6) Uani 1 1 d . . . O1 O 0.8494(2) 0.11575(16) 1.16038(16) 0.0631(6) Uani 1 1 d . . . O2 O 1.0775(2) 0.07697(18) 1.12378(19) 0.0693(6) Uani 1 1 d . . . O3 O 1.2310(2) 0.2247(2) 1.0822(2) 0.0787(7) Uani 1 1 d . . . O4 O 1.1396(2) 0.3257(2) 0.9063(3) 0.0969(10) Uani 1 1 d . . . O5 O 0.88196(19) 0.2340(2) 0.82706(19) 0.0705(7) Uani 1 1 d . . . P1 P 0.70593(7) 0.33362(6) 1.04385(7) 0.0568(2) Uani 1 1 d . . . P2 P 0.75542(7) 0.15089(6) 1.08777(6) 0.0548(2) Uani 1 1 d . . . P3 P 0.76963(6) 0.21457(6) 0.87996(6) 0.0491(2) Uani 1 1 d . . . Cl1 Cl 0.55524(9) 0.38326(10) 1.06060(11) 0.1028(4) Uani 1 1 d . . . Cl2 Cl 0.78870(10) 0.44771(8) 1.09158(9) 0.0889(4) Uani 1 1 d . . . Cl3 Cl 0.63363(10) 0.06188(9) 1.12548(11) 0.0961(4) Uani 1 1 d . . . H4N H 0.714(2) 0.197(2) 0.734(2) 0.035(9) 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 C1 0.084(2) 0.0502(18) 0.062(2) 0.0043(15) -0.0068(17) 0.0084(16) C2 0.094(3) 0.061(2) 0.064(2) 0.0043(17) -0.0166(19) 0.0160(19) C3 0.091(3) 0.062(2) 0.097(3) -0.021(2) -0.035(2) 0.017(2) C4 0.069(3) 0.115(4) 0.106(3) -0.053(3) -0.006(2) 0.009(3) C5 0.064(2) 0.168(5) 0.080(3) 0.000(3) 0.009(2) -0.018(3) C6 0.068(3) 0.157(5) 0.086(3) 0.007(3) 0.011(2) -0.007(3) C7 0.068(3) 0.141(5) 0.150(5) -0.056(4) 0.014(3) -0.029(3) C8 0.061(3) 0.138(5) 0.215(7) -0.086(5) -0.006(3) -0.015(3) C9 0.0566(18) 0.0611(19) 0.0532(17) 0.0029(14) -0.0041(14) -0.0052(15) C10 0.059(2) 0.103(3) 0.144(4) -0.038(3) 0.002(3) 0.008(2) C11 0.070(2) 0.078(3) 0.087(3) -0.017(2) -0.015(2) -0.0055(19) N1 0.091(2) 0.0632(17) 0.0485(15) -0.0062(13) 0.0041(14) 0.0167(15) N2 0.0771(18) 0.0506(14) 0.0429(13) -0.0024(11) -0.0058(12) 0.0147(12) N3 0.081(2) 0.0506(15) 0.0530(15) -0.0003(12) -0.0119(13) 0.0092(13) N4 0.0564(16) 0.0589(16) 0.0397(13) 0.0062(13) -0.0019(11) -0.0038(12) O1 0.0841(16) 0.0601(13) 0.0448(11) -0.0016(10) -0.0117(11) 0.0135(12) O2 0.0743(16) 0.0724(15) 0.0607(14) -0.0033(12) -0.0147(12) 0.0112(13) O3 0.0774(17) 0.102(2) 0.0572(14) -0.0117(14) 0.0094(12) -0.0005(15) O4 0.0624(17) 0.091(2) 0.137(3) -0.0046(19) -0.0176(17) -0.0153(15) O5 0.0543(13) 0.0908(18) 0.0664(14) -0.0076(13) 0.0005(11) -0.0116(12) P1 0.0609(5) 0.0512(5) 0.0580(5) -0.0091(4) -0.0106(4) 0.0109(4) P2 0.0686(5) 0.0521(5) 0.0437(4) 0.0005(3) -0.0006(4) 0.0077(4) P3 0.0517(4) 0.0529(4) 0.0424(4) -0.0005(3) -0.0052(3) 0.0029(3) Cl1 0.0696(7) 0.1091(9) 0.1293(10) -0.0360(8) -0.0141(6) 0.0345(6) Cl2 0.1049(8) 0.0706(6) 0.0906(7) -0.0195(5) -0.0225(6) -0.0127(5) Cl3 0.0919(8) 0.0900(8) 0.1071(9) 0.0017(6) 0.0240(6) -0.0164(6) _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 C1 O1 1.453(4) . ? C1 C2 1.483(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 O2 1.403(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O2 1.418(5) . ? C3 C4 1.482(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 O3 1.412(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 O3 1.434(5) . ? C5 C6 1.436(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 O4 1.416(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.306(7) . ? C7 O4 1.375(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O5 1.448(5) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 N4 1.462(4) . ? C9 C11 1.505(5) . ? C9 C10 1.511(5) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? N1 P1 1.568(3) . ? N1 P2 1.579(3) . ? N2 P2 1.561(3) . ? N2 P3 1.583(3) . ? N3 P1 1.553(3) . ? N3 P3 1.609(3) . ? N4 P3 1.604(3) . ? N4 H4N 0.67(3) . ? O1 P2 1.549(2) . ? O5 P3 1.571(2) . ? P1 Cl2 1.9968(14) . ? P1 Cl1 2.0019(14) . ? P2 Cl3 2.0220(15) . ? 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 C1 C2 108.9(3) . . ? O1 C1 H1A 109.9 . . ? C2 C1 H1A 109.9 . . ? O1 C1 H1B 109.9 . . ? C2 C1 H1B 109.9 . . ? H1A C1 H1B 108.3 . . ? O2 C2 C1 109.4(3) . . ? O2 C2 H2A 109.8 . . ? C1 C2 H2A 109.8 . . ? O2 C2 H2B 109.8 . . ? C1 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? O2 C3 C4 110.1(4) . . ? O2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? O2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.2 . . ? O3 C4 C3 109.9(3) . . ? O3 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? O3 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? O3 C5 C6 114.6(4) . . ? O3 C5 H5A 108.6 . . ? C6 C5 H5A 108.6 . . ? O3 C5 H5B 108.6 . . ? C6 C5 H5B 108.6 . . ? H5A C5 H5B 107.6 . . ? O4 C6 C5 109.8(4) . . ? O4 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? O4 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C8 C7 O4 114.2(5) . . ? C8 C7 H7A 108.7 . . ? O4 C7 H7A 108.7 . . ? C8 C7 H7B 108.7 . . ? O4 C7 H7B 108.7 . . ? H7A C7 H7B 107.6 . . ? C7 C8 O5 114.8(5) . . ? C7 C8 H8A 108.6 . . ? O5 C8 H8A 108.6 . . ? C7 C8 H8B 108.6 . . ? O5 C8 H8B 108.6 . . ? H8A C8 H8B 107.5 . . ? N4 C9 C11 109.0(3) . . ? N4 C9 C10 111.7(3) . . ? C11 C9 C10 111.2(3) . . ? N4 C9 H9 108.3 . . ? C11 C9 H9 108.3 . . ? C10 C9 H9 108.3 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P1 N1 P2 118.82(17) . . ? P2 N2 P3 124.23(17) . . ? P1 N3 P3 123.56(17) . . ? C9 N4 P3 124.9(2) . . ? C9 N4 H4N 116(3) . . ? P3 N4 H4N 113(3) . . ? C1 O1 P2 121.8(2) . . ? C2 O2 C3 111.3(3) . . ? C4 O3 C5 117.8(4) . . ? C7 O4 C6 112.1(4) . . ? C8 O5 P3 120.1(3) . . ? N3 P1 N1 120.00(15) . . ? N3 P1 Cl2 110.29(13) . . ? N1 P1 Cl2 107.91(13) . . ? N3 P1 Cl1 109.11(12) . . ? N1 P1 Cl1 108.44(13) . . ? Cl2 P1 Cl1 99.05(7) . . ? O1 P2 N2 112.27(14) . . ? O1 P2 N1 106.36(15) . . ? N2 P2 N1 119.36(15) . . ? O1 P2 Cl3 102.39(11) . . ? N2 P2 Cl3 106.63(12) . . ? N1 P2 Cl3 108.48(13) . . ? O5 P3 N2 111.52(15) . . ? O5 P3 N4 99.84(14) . . ? N2 P3 N4 109.02(15) . . ? O5 P3 N3 107.24(16) . . ? N2 P3 N3 113.47(14) . . ? N4 P3 N3 114.93(15) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.612 _refine_diff_density_min -0.298 _refine_diff_density_rms 0.074