#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/60/2006081.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2006081 loop_ _publ_author_name 'Barbati, S.' 'Siri, D.' 'Tordo, P.' 'Reboul, J.-P.' _publ_contact_author ; Jean Pierre Reboul GERCTOP. URA CNRS 1411 Facult\'e de Pharmacie 27, Boulevard Jean-Moulin 13385, Marseille-C\'edex 5 France ; _publ_section_title ; (N-Hydroxy-2-m\'ethylpyrrolidin-2-yl)phosphonate de Di\'ethyle ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 461 _journal_page_last 463 _journal_paper_doi 10.1107/S0108270196014448 _journal_volume 53 _journal_year 1997 _chemical_formula_analytical 'C9 H20 N O4 P ' _chemical_formula_structural (HO)(NCH2CH2CH2C)(PO(OEt)2) _chemical_formula_sum 'C9 H20 N O4 P' _chemical_formula_weight 237.24 _chemical_melting_point 310.15 _chemical_name_systematic ; [N-hydroxy-2-m\'ethylpyrrolidin-2-yl] phosphonate de di\'ethyle ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.468(2) _cell_length_b 9.778(3) _cell_length_c 15.193(1) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 56.00 _cell_measurement_theta_min 2.00 _cell_volume 1258.0(5) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1977)' _computing_data_reduction 'SDP (Frenz, 1978)' _computing_molecular_graphics 'ORTEP (Johnson, 1965)' _computing_publication_material 'Word 5.1a sur Macintoch IIvx' _computing_structure_solution 'MULTAN80 (Main et al., 1980)' _diffrn_ambient_temperature 293 _diffrn_measurement_device 'Enraf-Nonius CAD-4 ' _diffrn_measurement_method \q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71069 _diffrn_reflns_av_R_equivalents 0.02 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4112 _diffrn_reflns_reduction_process 'Programme SDP ENRAF NONIUS' _diffrn_reflns_theta_max 56 _diffrn_reflns_theta_min 2 _diffrn_standards_decay_% 3 _diffrn_standards_interval_time 120 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.22 _exptl_absorpt_correction_type none _exptl_crystal_colour incolore _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas 1.25(1) _exptl_crystal_density_method flottaison _exptl_crystal_description 'petit prisme' _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.3 _refine_diff_density_max .2 _refine_diff_density_min -.2 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all .21 _refine_ls_goodness_of_fit_obs .21 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 136 _refine_ls_number_reflns 1133 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.819 _refine_ls_restrained_S_obs 0.81 _refine_ls_R_factor_all .033 _refine_ls_R_factor_obs .033 _refine_ls_shift/esd_max .3 _refine_ls_structure_factor_coef F _refine_ls_weighting_details 'w = 1/\s' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .032 _refine_ls_wR_factor_obs .032 _reflns_number_observed 1441 _reflns_number_total 2922 _reflns_observed_criterion 'I > 3\s(I)' _cod_data_source_file pa1234.cif _cod_data_source_block barbati _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '37 C' was changed to '310.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/\s' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/\s'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1258.0(10) _cod_original_formula_sum 'C9 H20 N O4 P ' _cod_database_code 2006081 _cod_database_fobs_code 2006081 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '1/2-x, -y,1/2+z' 1/2+x,1/2-y,-z -x,1/2+y,1/2-z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_22 _atom_site_aniso_U_23 _atom_site_aniso_U_33 _atom_site_aniso_type_symbol C1 0.045(2) 0.005(2) 0.007(2) 0.035(1) 0.002(2) 0.075(2) C C2 0.063(2) 0.008(2) -0.019(2) 0.053(2) 0.003(2) 0.093(2) C C3 0.065(1) 0.001(1) 0.021(2) 0.041(1) 0.022(1) 0.114(2) C C4 0.079(3) -0.004(2) -0.019(2) 0.052(2) -0.011(2) 0.099(3) C C5 0.064(2) 0.002(2) 0.032(2) 0.060(2) 0.011(3) 0.114(3) C C6 0.076(3) 0.023(2) -0.009(2) 0.075(2) -0.006(2) 0.089(3) C C61 0.133(4) 0.046(3) -0.021(3) 0.081(3) -0.001(3) 0.089(3) C C7 0.083(3) -0.007(2) 0.014(3) 0.063(2) -0.022(2) 0.108(3) C C71 0.106(4) -0.002(3) 0.021(3) 0.065(2) -0.032(3) 0.123(3) C P 0.0500(4) 0.0004(5) 0.0043(5) 0.0434(4) -0.0020(5) 0.0629(4) P O1 0.059(1) -0.017(1) 0.010(1) 0.055(1) -0.005(1) 0.073(1) O O2 0.064(1) 0.000(1) 0.007(2) 0.051(1) -0.016(1) 0.093(2) O O3 0.065(1) 0.001(1) 0.021(2) 0.041(1) 0.022(1) 0.114(2) O O4 0.068(1) 0.022(1) 0.003(1) 0.079(2) -0.001(1) 0.065(1) O N 0.051(2) -0.000(1) 0.005(2) 0.035(1) 0.007(1) 0.080(2) N loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_B_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_type_symbol C1 0.3007(4) 0.5357(3) 0.7257(2) 4.08(7) Beq d C C2 0.3733(5) 0.4600(4) 0.8056(3) 5.49(8) Beq d C C3 0.3383(5) 0.5502(5) 0.8852(3) 6.6(1) Beq d C C4 0.3337(5) 0.6918(4) 0.8440(3) 6.1(1) Beq d C C5 0.4208(5) 0.5573(4) 0.6515(3) 6.3(1) Beq d C C6 -0.0889(5) 0.6100(4) 0.6207(3) 6.3(1) Beq d C C61 -0.1044(6) 0.6998(3) 0.5457(3) 8.0(1) Beq d C C7 0.1013(5) 0.2111(4) 0.6060(3) 6.7(1) Beq d C C71 0.1954(6) 0.0983(4) 0.5774(3) 7.8(1) Beq d C P 0.1262(1) 0.4463(1) 0.6895(1) 4.11(2) Beq d P O1 0.0146(3) 0.4148(2) 0.7605(2) 4.91(5) Beq d O O2 0.0511(3) 0.5279(3) 0.6116(2) 5.59(6) Beq d O O3 0.1997(3) 0.3182(2) 0.6420(2) 5.46(6) Beq d O O4 0.2568(3) 0.7785(2) 0.7059(2) 5.81(6) Beq d O N 0.2401(3) 0.6659(3) 0.7656(2) 4.39(6) Beq d N H21 0.4962 0.4498 0.8002 ? ? ? H H22 0.3288 0.3630 0.8138 ? ? ? H H31 0.4171 0.5411 0.9358 ? ? ? H H32 0.2261 0.5251 0.9120 ? ? ? H H41 0.2817 0.7647 0.8857 ? ? ? H H42 0.4461 0.7266 0.8308 ? ? ? H H51 0.4597 0.4674 0.6257 ? ? ? H H52 0.3722 0.6150 0.6010 ? ? ? H H53 0.5188 0.6114 0.6741 ? ? ? H H61 -0.0887 0.6645 0.6774 ? ? ? H H62 -0.1890 0.5465 0.6215 ? ? ? H H611 -0.2010 0.7594 0.5492 ? ? ? H H612 -0.0046 0.7630 0.5440 ? ? ? H H613 -0.1049 0.6450 0.4881 ? ? ? H H71 0.0366 0.2490 0.5512 ? ? ? H H72 0.0173 0.1780 0.6503 ? ? ? H H711 0.1304 0.0205 0.5496 ? ? ? H H712 0.2771 0.1298 0.5303 ? ? ? H H713 0.2578 0.0588 0.6294 ? ? ? H H04 0.1659 0.8339 0.7226 ? ? ? H loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source P .009 .095 International_Tables_Vol_IV_Table_2.3.1 O .008 .006 International_Tables_Vol_IV_Table_2.3.1 N .004 .003 International_Tables_Vol_IV_Table_2.3.1 C .002 .002 International_Tables_Vol_IV_Table_2.3.1 H .000 .000 International_Tables_Vol_IV_Table_2.3.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 0 0 2 2 1 0 1 0 1 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 P O1 113.9(2) yes C1 P O2 108.5(2) yes C1 P O3 101.60(10) yes C1 N C4 107.0(3) yes C1 N O4 111.2(2) yes O1 P O2 113.7(2) yes O1 P O3 115.2(2) yes O2 P O3 102.7(2) yes C4 N O4 109.3(3) yes P C1 C2 109.4(2) yes N C1 C2 103.0(3) yes P C1 C5 112.7(2) yes N C1 C5 114.0(3) yes P C1 N 104.7(2) yes C2 C1 C5 112.3(3) yes P O2 C6 123.2(3) yes C1 C2 C3 105.5(3) yes P O3 C7 121.5(2) yes C2 C3 C4 101.8(3) yes N C4 C3 101.1(3) yes O2 C6 C61 109.8(3) yes O3 C7 C71 110.7(3) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag P . C1 . 1.803(3) yes N . C1 . 1.501(4) yes N . C4 . 1.453(5) yes P . O1 . 1.467(3) yes P . O2 . 1.563(3) yes P . O3 . 1.574(3) yes N . O4 . 1.433(4) yes C1 . C2 . 1.549(5) yes C1 . C5 . 1.533(5) yes C2 . C3 . 1.526(6) yes O2 . C6 . 1.438(5) yes C3 . C4 . 1.520(6) yes O3 . C7 . 1.446(5) yes C6 . C61 . 1.445(6) yes C7 . C71 . 1.428(6) yes 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_publ_flag N C1 P O1 -60.0(2) yes N C1 P O2 67.8(2) yes N C1 P O3 175.6(2) yes P C1 N C4 139.9(3) yes P C1 N O4 -100.8(2) yes P C1 C2 C3 -107.5(3) yes N C1 C2 C3 3.4(2) yes P O2 C6 C61 164.7(3) yes P O3 C7 C71 -172.1(3) yes N C4 C3 C2 44.6(2) yes O1 P C1 C2 49.9(2) yes O1 P C1 C5 175.5(3) yes C1 P O2 C6 -104.7(2) yes O1 P O2 C6 23.1(2) yes C1 P O3 C7 176.4(2) yes O1 P O3 C7 52.8(2) yes C1 N C4 C3 -44.3(2) yes C1 C2 C3 C4 -29.2(2) yes O2 P C1 C5 -56.7(2) yes O2 P O3 C7 -71.4(2) yes C2 C1 P O2 177.6(2) yes C2 C1 P O3 -74.6(2) yes C2 C1 N C4 25.5(2) yes C2 C1 N O4 144.8(3) yes O3 P C1 C5 51.1(2) yes O3 P O2 C6 148.2(2) yes C3 C2 C1 C5 126.5(3) yes C3 C4 N O4 -164.9(3) yes C4 N C1 C5 -96.4(3) yes O4 N C1 C5 22.9(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139055466