#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/32/2203207.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_2203207 loop_ _publ_author_name 'Maria Gdaniec' 'Maria J. Milewska' 'Tadeusz Po\/lo\'nski' _publ_section_title ; (S)-N-Nitrosoazetidine-2-carboxylic acid ; _journal_issue 2 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o181 _journal_page_last o183 _journal_paper_doi 10.1107/S1600536804000327 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C4 H6 N2 O3' _chemical_formula_moiety 'C4 H6 N2 O3' _chemical_formula_sum 'C4 H6 N2 O3' _chemical_formula_weight 130.11 _chemical_melting_point 388.5(5) _chemical_name_systematic ; (S)-Nitrosoazetidine-2-carboxylic acid ; _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' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.6521(11) _cell_length_b 7.948(2) _cell_length_c 10.848(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30 _cell_measurement_theta_min 13 _cell_volume 573.5(2) _computing_cell_refinement 'KM-4 Software (Kuma, 1991)' _computing_data_reduction 'KM-4 Software' _computing_molecular_graphics 'Stereochemical Workstation Operation Manual (Siemens, 1989)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device 'Kuma KM-4 four-circle' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0340 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_max 0 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 1160 _diffrn_reflns_theta_full 67.83 _diffrn_reflns_theta_max 67.83 _diffrn_reflns_theta_min 6.91 _diffrn_standards_decay_% <1.5 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.131 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.507 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 272 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.137 _refine_diff_density_min -0.151 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 82 _refine_ls_number_reflns 630 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0350 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0623P)^2^+0.0432P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0980 _refine_ls_wR_factor_ref 0.1002 _reflns_number_gt 586 _reflns_number_total 630 _reflns_threshold_expression I>2\s(I) _cod_data_source_file na6283.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '388-389 K' was changed to '388.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '388-389 K' was changed to '388.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2203207 _cod_database_fobs_code 2203207 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' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol O1 0.8442(3) 0.7297(2) 0.53813(13) 0.0642(5) Uani d . 1 O O2 0.8536(3) 0.5374(2) 0.38881(14) 0.0613(5) Uani d . 1 O H2O 0.8502 0.4694 0.4492 0.074 Uiso d R 1 H O3 0.6429(3) 0.6975(2) 0.05219(13) 0.0567(5) Uani d . 1 O N1 0.7527(3) 0.7920(2) 0.22005(14) 0.0466(5) Uani d . 1 N N2 0.7704(3) 0.6787(2) 0.13624(15) 0.0508(5) Uani d . 1 N C1 0.8738(3) 0.8222(2) 0.33104(18) 0.0458(5) Uani d . 1 C H11 1.0136 0.8399 0.3134 0.055 Uiso d R 1 H C2 0.7521(4) 0.9866(3) 0.3482(2) 0.0517(6) Uani d . 1 C H21 0.8353 1.0849 0.3417 0.062 Uiso d R 1 H H22 0.6762 0.9890 0.4235 0.062 Uiso d R 1 H C3 0.6247(4) 0.9412(3) 0.2340(2) 0.0544(6) Uani d . 1 C H31 0.4864 0.9254 0.2563 0.065 Uiso d R 1 H H32 0.6294 1.0078 0.1601 0.065 Uiso d R 1 H C4 0.8530(4) 0.6919(3) 0.43120(19) 0.0456(5) Uani d . 1 C loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0947(13) 0.0598(9) 0.0382(9) 0.0087(11) -0.0002(9) -0.0040(8) O2 0.0956(12) 0.0463(8) 0.0418(9) -0.0022(10) -0.0016(9) 0.0010(7) O3 0.0713(10) 0.0529(8) 0.0460(9) -0.0021(9) -0.0076(8) -0.0003(7) N1 0.0590(10) 0.0428(8) 0.0379(9) 0.0026(9) 0.0010(8) -0.0025(8) N2 0.0632(10) 0.0489(10) 0.0404(9) -0.0032(9) 0.0007(8) 0.0039(8) C1 0.0484(11) 0.0473(10) 0.0417(11) -0.0006(10) 0.0008(9) -0.0014(10) C2 0.0616(11) 0.0394(9) 0.0542(12) -0.0007(9) 0.0024(12) -0.0046(10) C3 0.0690(14) 0.0446(11) 0.0497(13) 0.0088(12) -0.0024(11) 0.0036(10) C4 0.0462(10) 0.0478(11) 0.0428(11) 0.0017(11) -0.0025(9) -0.0017(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 C4 O2 H2O 109.0 ? N2 N1 C3 133.81(18) y N2 N1 C1 130.13(18) y C3 N1 C1 95.83(16) y O3 N2 N1 111.61(18) y N1 C1 C4 115.36(17) y N1 C1 C2 87.14(16) y C4 C1 C2 116.42(18) y N1 C1 H11 113.1 ? C4 C1 H11 109.4 ? C2 C1 H11 114.0 ? C3 C2 C1 89.60(16) y C3 C2 H21 116.6 ? C1 C2 H21 112.1 ? C3 C2 H22 113.5 ? C1 C2 H22 113.2 ? H21 C2 H22 110.5 ? N1 C3 C2 87.31(16) y N1 C3 H31 118.4 ? C2 C3 H31 110.7 ? N1 C3 H32 109.9 ? C2 C3 H32 121.5 ? H31 C3 H32 108.3 ? O1 C4 O2 125.0(2) y O1 C4 C1 122.0(2) y O2 C4 C1 112.97(18) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C4 1.200(2) y O2 C4 1.311(3) y O2 H2O 0.85 ? O3 N2 1.254(2) y N1 N2 1.285(2) y N1 C3 1.468(3) y N1 C1 1.468(3) y C1 C4 1.507(3) y C1 C2 1.548(3) y C1 H11 0.96 ? C2 C3 1.544(3) y C2 H21 0.96 ? C2 H22 0.96 ? C3 H31 0.96 ? C3 H32 0.96 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA O2 H2O O3 2_665 0.85 1.73 2.575(2) 169 C3 H32 O1 2_674 0.96 2.48 3.376(3) 156 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 C3 N1 N2 O3 -4.1(3) y C1 N1 N2 O3 -177.16(19) y N2 N1 C1 C4 -69.7(3) y C3 N1 C1 C4 115.3(2) ? N2 N1 C1 C2 172.3(2) ? C3 N1 C1 C2 -2.68(17) y N1 C1 C2 C3 2.54(16) y C4 C1 C2 C3 -114.5(2) ? N2 N1 C3 C2 -172.0(2) ? C1 N1 C3 C2 2.69(17) ? C1 C2 C3 N1 -2.54(16) ? N1 C1 C4 O1 -139.2(2) ? C2 C1 C4 O1 -39.2(3) ? N1 C1 C4 O2 43.2(3) ? C2 C1 C4 O2 143.3(2) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 20163476 2 PubChem 15089039