#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008939.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_2008939 loop_ _publ_author_name 'Tokutake, Nobuya' 'Hiratake, Jun' 'Irie, Takayuki' 'Yamano, Akihito' 'Oda, Jun-ichi' _publ_section_title ; The absolute configuration of an intermediate cyclic sulfoximine in the asymmetric synthesis of transition-state analog inhibitors of \g-glutamylcysteine synthetase ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1598 _journal_page_last 1599 _journal_paper_doi 10.1107/S0108270198016436 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C9 H16 N2 O4 S' _chemical_formula_sum 'C9 H16 N2 O4 S' _chemical_formula_weight 248.30 _chemical_melting_point 203 _space_group_IT_number 4 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _cell_angle_alpha 90 _cell_angle_beta 92.243(7) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 10.5450(10) _cell_length_b 9.7470(10) _cell_length_c 5.3893(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 298.2 _cell_measurement_theta_max 17.2 _cell_measurement_theta_min 15.1 _cell_volume 553.50(9) _computing_cell_refinement 'Rigaku/AFC Diffractometer Control Software' _computing_data_collection 'Rigaku/AFC Diffractometer Control Software (Rigaku Corporation, 1998)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation/Rigaku Corporation, 1998)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_measured_fraction_theta_full 1.0000 _diffrn_measured_fraction_theta_max 1.0000 _diffrn_measurement_device_type 'Rigaku AFC-7R' _diffrn_measurement_method \w-2\q _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.7107 _diffrn_reflns_av_R_equivalents 0.027 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 3418 _diffrn_reflns_theta_full 29.99 _diffrn_reflns_theta_max 29.99 _diffrn_standards_decay_% 0.30 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.490 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _refine_diff_density_max 0.32 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment noref _refine_ls_number_parameters 144 _refine_ls_number_reflns 1709 _refine_ls_R_factor_gt 0.029 _refine_ls_shift/su_max 0.0008 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + 0.00422(Fo^2^)^2^]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.084 _reflns_number_gt 1649 _reflns_number_total 1709 _reflns_threshold_expression F^2^>2\s(F^2^) _cod_data_source_file oa1081.cif _cod_data_source_block xr0015 _cod_original_cell_volume 553.50(10) _cod_original_sg_symbol_H-M 'P 21' _cod_database_code 2008939 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,-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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol S1 0.13861(3) 0.3065 0.13142(7) 0.02580(9) Uani d S 1.00 . . S O1 0.5629(2) 0.1212(2) 0.7394(2) 0.0387(4) Uani d . 1.00 . . O O2 0.48170(10) 0.3332(2) 0.7372(2) 0.0331(3) Uani d . 1.00 . . O O3 0.1643(2) 0.2976(3) -0.1288(2) 0.0521(5) Uani d . 1.00 . . O O4 -0.13840(10) 0.1538(2) 0.3845(4) 0.0561(5) Uani d . 1.00 . . O N1 0.58920(10) 0.1140(2) 0.2484(2) 0.0234(3) Uani d . 1.00 . . N N2 0.0588(2) 0.1836(2) 0.2347(4) 0.0362(4) Uani d . 1.00 . . N C1 0.5192(2) 0.2271(2) 0.6355(3) 0.0237(3) Uani d . 1.00 . . C C2 0.50670(10) 0.2233(2) 0.3494(3) 0.0209(3) Uani d . 1.00 . . C C3 0.3698(2) 0.1971(2) 0.2573(3) 0.0239(3) Uani d . 1.00 . . C C4 0.28440(10) 0.3193(2) 0.3077(3) 0.0263(3) Uani d . 1.00 . . C C5 0.0442(2) 0.4503(2) 0.2065(4) 0.0307(4) Uani d . 1.00 . . C C6 -0.0626(2) 0.3874(2) 0.3512(3) 0.0298(4) Uani d . 1.00 . . C C7 -0.0529(2) 0.2312(2) 0.3247(4) 0.0317(4) Uani d . 1.00 . . C C8 -0.1958(2) 0.4361(3) 0.2710(5) 0.0404(5) Uani d . 1.00 . . C C9 -0.2331(2) 0.3969(3) 0.0077(5) 0.0486(6) Uani d . 1.00 . . C H1 0.5657 0.0289 0.2878 0.0281 Uiso d . 1.00 . . H H2 0.5790 0.1192 0.0940 0.0281 Uiso d . 1.00 . . H H3 0.6722 0.1232 0.3048 0.0281 Uiso d . 1.00 . . H H4 0.5324 0.3061 0.2827 0.0443 Uiso d . 1.00 . . H H5 0.3368 0.1102 0.3239 0.0443 Uiso d . 1.00 . . H H6 0.3665 0.1810 0.0839 0.0443 Uiso d . 1.00 . . H H7 0.2627 0.3165 0.4935 0.0443 Uiso d . 1.00 . . H H8 0.3263 0.4005 0.2590 0.0443 Uiso d . 1.00 . . H H9 -0.2518 0.3966 0.3812 0.0443 Uiso d . 1.00 . . H H10 -0.1926 0.5334 0.2874 0.0443 Uiso d . 1.00 . . H H11 0.0137 0.4864 0.0389 0.0443 Uiso d . 1.00 . . H H12 0.0938 0.5153 0.3216 0.0443 Uiso d . 1.00 . . H H13 -0.2122 0.3053 -0.0273 0.0583 Uiso d . 1.00 . . H H14 -0.3212 0.3964 -0.0571 0.0583 Uiso d . 1.00 . . H H15 -0.1942 0.4348 -0.0989 0.0583 Uiso d . 1.00 . . H H16 -0.0483 0.4127 0.5296 0.0443 Uiso d . 1.00 . . H 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 S1 0.0205(2) 0.0328(2) 0.0239(2) 0.0019(2) -0.00240(10) -0.0030(2) O1 0.0608(9) 0.0373(8) 0.0181(5) 0.0181(7) 0.0014(6) 0.0020(5) O2 0.0392(7) 0.0332(8) 0.0265(6) 0.0067(6) -0.0026(5) -0.0065(5) O3 0.0435(8) 0.0890(10) 0.0236(6) 0.0120(10) -0.0013(5) -0.0076(9) O4 0.0301(8) 0.0540(10) 0.0830(10) -0.0119(7) -0.0094(8) 0.0359(10) N1 0.0232(6) 0.0303(7) 0.0166(5) 0.0020(5) 0.0010(4) 0.0009(5) N2 0.0267(8) 0.0256(8) 0.0560(10) 0.0002(6) -0.0066(7) -0.0023(7) C1 0.0238(7) 0.0310(8) 0.0160(6) -0.0009(6) -0.0014(5) -0.0003(6) C2 0.0191(6) 0.0260(7) 0.0175(6) -0.0008(5) 0.0000(5) 0.0019(5) C3 0.0200(6) 0.0308(8) 0.0208(6) -0.0025(6) -0.0018(5) -0.0017(6) C4 0.0188(6) 0.0328(8) 0.0271(7) -0.0007(7) -0.0021(5) -0.0038(7) C5 0.0244(8) 0.0243(8) 0.0432(10) -0.0001(7) -0.0015(7) -0.0008(7) C6 0.0268(8) 0.0368(10) 0.0259(8) 0.0006(7) 0.0024(6) -0.0030(7) C7 0.0234(8) 0.0326(9) 0.0382(9) -0.0034(7) -0.0081(7) 0.0112(8) C8 0.0240(8) 0.0390(10) 0.0590(10) 0.0053(8) 0.0074(8) 0.0014(10) C9 0.0350(10) 0.0510(10) 0.0590(10) -0.0087(10) -0.0161(9) 0.0230(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.125 0.123 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; O O 0.011 0.006 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; N N 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; C C 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H H 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 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 O3 S1 N2 114.90(10) yes O3 S1 C4 109.40(8) yes O3 S1 C5 113.40(10) yes N2 S1 C4 109.08(10) yes N2 S1 C5 101.97(8) yes C4 S1 C5 107.64(9) yes C2 N1 H1 113.90(10) no C2 N1 H2 105.40(10) no C2 N1 H3 111.70(10) no H1 N1 H2 105.5(2) no H1 N1 H3 106.4(2) no H2 N1 H3 114.00(10) no S1 N2 C7 110.20(10) yes O1 C1 O2 127.30(10) no O1 C1 C2 116.20(10) no O2 C1 C2 116.40(10) no N1 C2 C1 110.70(10) no N1 C2 C3 108.60(10) no N1 C2 H4 107.30(10) no C1 C2 C3 111.70(10) no C1 C2 H4 110.60(10) no C3 C2 H4 107.70(10) no C2 C3 C4 111.60(10) no C2 C3 H5 111.5(2) no C2 C3 H6 110.20(10) no C4 C3 H5 112.70(10) no C4 C3 H6 107.8(2) no H5 C3 H6 102.5(2) no S1 C4 C3 110.70(10) no S1 C4 H7 107.10(10) no S1 C4 H8 108.30(10) no C3 C4 H7 107.8(2) no C3 C4 H8 108.60(10) no H7 C4 H8 114.3(2) no S1 C5 C6 103.40(10) yes S1 C5 H11 103.5(2) no S1 C5 H12 110.60(10) no C6 C5 H11 112.5(2) no C6 C5 H12 108.1(2) no H11 C5 H12 117.7(2) no C5 C6 C7 107.4(2) yes C5 C6 C8 114.8(2) no C5 C6 H16 107.8(2) no C7 C6 C8 110.2(2) no C7 C6 H16 109.0(2) no C8 C6 H16 107.4(2) no O4 C7 N2 122.3(2) no O4 C7 C6 122.2(2) no N2 C7 C6 115.5(2) yes C6 C8 C9 113.0(2) no C6 C8 H9 106.7(2) no C6 C8 H10 104.7(2) no C9 C8 H9 110.2(2) no C9 C8 H10 110.3(2) no H9 C8 H10 111.8(2) no C8 C9 H13 112.0(2) no C8 C9 H14 123.1(3) no C8 C9 H15 115.7(2) no H13 C9 H14 98.6(2) no H13 C9 H15 99.3(3) no H14 C9 H15 104.4(2) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 . . 1.4410(10) yes S1 N2 . . 1.577(2) yes S1 C4 . . 1.780(2) yes S1 C5 . . 1.775(2) yes O1 C1 . . 1.253(2) no O2 C1 . . 1.242(2) no O4 C7 . . 1.228(3) no N1 C2 . . 1.492(2) no N1 H1 . . 0.893 no N1 H2 . . 0.837 no N1 H3 . . 0.919 no N2 C7 . . 1.373(3) no C1 C2 . . 1.543(2) no C2 C3 . . 1.530(2) no C2 H4 . . 0.928 no C3 C4 . . 1.524(3) no C3 H5 . . 0.988 no C3 H6 . . 0.947 no C4 H7 . . 1.037 no C4 H8 . . 0.948 no C5 C6 . . 1.524(3) no C5 H11 . . 1.010 no C5 H12 . . 1.017 no C6 C7 . . 1.533(3) no C6 C8 . . 1.528(3) no C6 H16 . . 0.998 no C8 C9 . . 1.507(4) no C8 H9) . . 0.937 no C8 H10 . . 0.953 no C9 H13 . . 0.940 no C9 H14 . . 0.980 no C9 H15 . . 0.808 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N1 2.747(2) 1_556 no O1 C4 3.368(3) 2_646 no O1 C2 3.507(2) 1_556 no O1 C3 3.596(2) 1_556 no O2 N1 2.839(2) 2_656 no O2 C9 3.349(3) 1_656 no O2 C3 3.357(2) 1_556 no O2 O3 3.469(2) 1_556 no O2 C2 3.469(2) 1_556 no O3 C4 3.343(2) 1_554 no O4 N1 2.962(2) 1_455 no O4 C5 3.100(3) 2_546 no N1 C1 3.533(2) 1_554 no N2 C5 3.436(3) 2_545 no C3 C9 3.538(3) 2_545 no 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 S1 N2 C7 O4 170.1(2) no S1 N2 C7 C6 -11.2(2) yes S1 C4 C3 C2 164.80(10) no S1 C5 C6 C7 -9.9(2) yes S1 C5 C6 C8 -132.9(2) no O1 C1 C2 N1 -19.4(2) no O1 C1 C2 C3 101.8(2) no O2 C1 C2 N1 162.40(10) no O2 C1 C2 C3 -76.4(2) no O3 S1 N2 C7 -119.2(2) no O3 S1 C4 C3 -57.6(2) no O3 S1 C5 C6 128.2(2) no O4 C7 C6 C5 -167.2(2) no O4 C7 C6 C8 -41.4(3) no N1 C2 C3 C4 -168.30(10) no N2 S1 C4 C3 68.80(10) no N2 S1 C5 C6 4.10(10) yes N2 C7 C6 C5 14.1(3) yes N2 C7 C6 C8 139.9(2) no C1 C2 C3 C4 69.3(2) no C3 C4 S1 C5 178.70(10) no C4 S1 N2 C7 117.5(2) no C4 S1 C5 C6 -110.60(10) no C5 S1 N2 C7 3.9(2) yes C5 C6 C8 C9 63.5(3) no C7 C6 C8 C9 -57.9(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 139056792