data_wh426a # chiral _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C5 H14 N2, H O3 P, H2 O' _chemical_formula_sum 'C5 H17 N2 O4 P' _chemical_formula_weight 200.18 _chemical_absolute_configuration syn 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.564(5) _cell_length_b 9.593(6) _cell_length_c 11.607(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 953.6(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 237 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 16.21 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 0.272 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Bruker SMART1000 CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 5970 _diffrn_reflns_av_R_equivalents 0.2468 _diffrn_reflns_av_sigmaI/netI 0.2079 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.75 _diffrn_reflns_theta_max 26.00 _reflns_number_total 1104 _reflns_number_gt 507 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'SHELXL-97' _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^)+(0.0035P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens 'difmap and geom' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details none _refine_ls_number_reflns 1104 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1598 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.0811 _refine_ls_wR_factor_gt 0.0650 _refine_ls_goodness_of_fit_ref 0.785 _refine_ls_restrained_S_all 0.785 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.0585(2) 0.03315(18) 0.52184(16) 0.0352(5) Uani 1 1 d . . . H1 H 0.0009 0.0933 0.6149 0.042 Uiso 1 1 calc R . . O1 O -0.0485(5) -0.0860(4) 0.4928(5) 0.0650(16) Uani 1 1 d . . . O2 O 0.2183(4) -0.0227(4) 0.5542(4) 0.0522(14) Uani 1 1 d . . . O3 O 0.0643(6) 0.1426(4) 0.4300(4) 0.0575(15) Uani 1 1 d . . . N1 N 0.1605(5) 0.6686(5) 0.4979(5) 0.0358(16) Uani 1 1 d . . . H1A H 0.2603 0.6391 0.5003 0.043 Uiso 1 1 calc R . . H1B H 0.1604 0.7607 0.5126 0.043 Uiso 1 1 calc R . . N2 N 0.0078(5) 0.4146(5) 0.4489(5) 0.0420(18) Uani 1 1 d . . . H2A H -0.0926 0.4422 0.4481 0.050 Uiso 1 1 calc R . . H2B H 0.0099 0.3223 0.4350 0.050 Uiso 1 1 calc R . . C1 C 0.0707(9) 0.5963(6) 0.5893(6) 0.044(2) Uani 1 1 d . . . H1C H -0.0364 0.6292 0.5900 0.053 Uiso 1 1 calc R . . H1D H 0.1167 0.6147 0.6641 0.053 Uiso 1 1 calc R . . C2 C 0.0752(8) 0.4423(7) 0.5637(5) 0.042(2) Uani 1 1 d . . . H2C H 0.1824 0.4096 0.5660 0.050 Uiso 1 1 calc R . . H2D H 0.0164 0.3921 0.6219 0.050 Uiso 1 1 calc R . . C3 C 0.0946(8) 0.4884(6) 0.3562(6) 0.0378(19) Uani 1 1 d . . . H3A H 0.0450 0.4706 0.2826 0.045 Uiso 1 1 calc R . . H3B H 0.2007 0.4533 0.3526 0.045 Uiso 1 1 calc R . . C4 C 0.0973(8) 0.6448(7) 0.3794(6) 0.0316(18) Uani 1 1 d . . . H4 H -0.0099 0.6804 0.3762 0.038 Uiso 1 1 calc R . . C5 C 0.1952(8) 0.7228(8) 0.2921(7) 0.055(2) Uani 1 1 d . . . H5A H 0.1885 0.8211 0.3068 0.082 Uiso 1 1 calc R . . H5B H 0.1573 0.7035 0.2160 0.082 Uiso 1 1 calc R . . H5C H 0.3020 0.6933 0.2982 0.082 Uiso 1 1 calc R . . O4 O 0.2874(6) 0.1764(6) 0.2631(4) 0.0723(18) Uani 1 1 d . . . H2 H 0.2128 0.1655 0.3094 0.087 Uiso 1 1 d R . . H3 H 0.2863 0.1255 0.1946 0.087 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 P1 0.0302(8) 0.0305(9) 0.0448(12) 0.0005(11) 0.0046(11) 0.0053(10) O1 0.035(2) 0.040(2) 0.119(5) -0.023(3) 0.004(4) -0.008(3) O2 0.031(2) 0.065(3) 0.061(4) 0.022(3) -0.004(2) 0.002(3) O3 0.080(3) 0.033(3) 0.060(4) 0.009(3) 0.017(3) 0.019(3) N1 0.038(3) 0.024(3) 0.045(5) 0.001(4) -0.006(3) 0.003(2) N2 0.030(3) 0.025(3) 0.071(5) -0.001(3) -0.011(3) 0.001(3) C1 0.049(5) 0.045(5) 0.037(5) -0.003(4) 0.008(5) -0.005(5) C2 0.029(4) 0.061(6) 0.034(5) 0.016(4) 0.002(4) -0.008(4) C3 0.034(4) 0.037(5) 0.043(5) -0.002(4) -0.001(3) -0.004(4) C4 0.026(4) 0.030(4) 0.039(5) -0.004(4) -0.008(4) 0.003(4) C5 0.058(5) 0.058(6) 0.049(6) 0.011(5) -0.011(5) -0.001(5) O4 0.072(4) 0.084(4) 0.061(5) -0.006(3) 0.005(3) -0.017(4) _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 O3 1.497(4) . y P1 O1 1.504(4) . y P1 O2 1.517(4) . y P1 H1 1.3200 . ? N1 C1 1.482(7) . ? N1 C4 1.496(8) . ? N1 H1A 0.9000 . ? N1 H1B 0.9000 . ? N2 C2 1.477(7) . ? N2 C3 1.487(7) . ? N2 H2A 0.9000 . ? N2 H2B 0.9000 . ? C1 C2 1.508(7) . ? C1 H1C 0.9700 . ? C1 H1D 0.9700 . ? C2 H2C 0.9700 . ? C2 H2D 0.9700 . ? C3 C4 1.525(8) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.513(9) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? O4 H2 0.8412 . ? O4 H3 0.9329 . ? 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 O3 P1 O1 113.2(3) . . y O3 P1 O2 113.2(3) . . y O1 P1 O2 109.7(2) . . y O3 P1 H1 106.8 . . ? O1 P1 H1 106.8 . . ? O2 P1 H1 106.8 . . ? C1 N1 C4 113.5(5) . . ? C1 N1 H1A 108.9 . . ? C4 N1 H1A 108.9 . . ? C1 N1 H1B 108.9 . . ? C4 N1 H1B 108.9 . . ? H1A N1 H1B 107.7 . . ? C2 N2 C3 111.8(4) . . ? C2 N2 H2A 109.3 . . ? C3 N2 H2A 109.3 . . ? C2 N2 H2B 109.3 . . ? C3 N2 H2B 109.3 . . ? H2A N2 H2B 107.9 . . ? N1 C1 C2 107.7(6) . . ? N1 C1 H1C 110.2 . . ? C2 C1 H1C 110.2 . . ? N1 C1 H1D 110.2 . . ? C2 C1 H1D 110.2 . . ? H1C C1 H1D 108.5 . . ? N2 C2 C1 110.1(6) . . ? N2 C2 H2C 109.6 . . ? C1 C2 H2C 109.6 . . ? N2 C2 H2D 109.6 . . ? C1 C2 H2D 109.6 . . ? H2C C2 H2D 108.2 . . ? N2 C3 C4 110.4(5) . . ? N2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? N2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N1 C4 C5 109.8(5) . . ? N1 C4 C3 108.5(5) . . ? C5 C4 C3 112.1(6) . . ? N1 C4 H4 108.8 . . ? C5 C4 H4 108.8 . . ? C3 C4 H4 108.8 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? H2 O4 H3 118.2 . . ? 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 C4 N1 C1 C2 59.6(7) . . . . ? C3 N2 C2 C1 59.7(7) . . . . ? N1 C1 C2 N2 -58.8(8) . . . . ? C2 N2 C3 C4 -57.2(6) . . . . ? C1 N1 C4 C5 179.7(6) . . . . ? C1 N1 C4 C3 -57.4(7) . . . . ? N2 C3 C4 N1 54.0(7) . . . . ? N2 C3 C4 C5 175.5(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.90 1.72 2.617(6) 179 4_556 N1 H1B O2 0.90 2.19 3.073(6) 167 1_565 N1 H1B O1 0.90 2.33 2.958(6) 127 1_565 N2 H2B O3 0.90 1.79 2.662(6) 164 . N2 H2A O2 0.90 1.79 2.688(6) 172 4_456 O4 H2 O3 0.84 1.91 2.741(7) 172 . O4 H3 O2 0.93 1.91 2.838(7) 179 2_554 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.222 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.055