#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/12/2011220.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_2011220 loop_ _publ_author_name 'Kassem, Tarek' 'Rolland, Val\'erie' 'Martinez, Jean' 'Rolland, Marc' _publ_section_title ; Two key chiral intermediates in a new 4-hydroxyisoleucine synthesis ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1037 _journal_page_last 1039 _journal_paper_doi 10.1107/S010827010000740X _journal_volume 56 _journal_year 2000 _chemical_formula_sum 'C16 H23 N O3' _chemical_formula_weight 277.364 _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 90.0000(10) _cell_angle_beta 90.0000(10) _cell_angle_gamma 90.0000(10) _cell_formula_units_Z 4 _cell_length_a 8.2610(3) _cell_length_b 12.5168(5) _cell_length_c 14.9291(3) _cell_measurement_reflns_used 11140 _cell_measurement_temperature 298 _cell_measurement_theta_max 26.37 _cell_measurement_theta_min 1.00 _cell_volume 1543.69(9) _computing_data_collection 'KappaCCD (Nonius, 1998)' _computing_data_reduction 'Denzo and Scalepak (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material maXus _computing_structure_refinement 'maXus (Mackay et al., 1999)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_measurement_device 'Kappa CCD area-detector' _diffrn_measurement_method \f-scan _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .028 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 10011 _diffrn_reflns_theta_max 26.37 _exptl_absorpt_coefficient_mu .082 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.193 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 600 _exptl_crystal_size_max .40 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .20 _refine_diff_density_max .17 _refine_diff_density_min -.31 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.309 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 1630 _refine_ls_R_factor_gt .039 _refine_ls_shift/su_max .001 _refine_ls_structure_factor_coef F^2^ _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + 0.03Fo^2^)]' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .060 _reflns_number_gt 1630 _reflns_number_total 1793 _reflns_threshold_expression I>3\s(I) _cod_data_source_file gs1091.cif _cod_data_source_block IV _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_atom_site_adp_type' tag value 'Uij' was replaced with 'Uani' value 20 times. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. 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^2^(Fo^2^) + 0.03Fo^2^)]' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^) + 0.03Fo^2^)]'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_formula_sum 'C16 H23 N O3 ' _cod_database_code 2011220 _cod_database_fobs_code 2011220 loop_ _symmetry_equiv_pos_as_xyz +X,+Y,+Z '-X+ 1/2,-Y,+Z+ 1/2' '+X+ 1/2,-Y+ 1/2,-Z' '-X,+Y+ 1/2,-Z+ 1/2' 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_occupancy O1 .84959(5) .37220(3) .77036(2) .0410(2) Uani 1.00 O2 .86251(5) .54706(3) .78450(3) .0531(2) Uani 1.00 O3 1.02798(6) .60814(4) .97029(3) .0733(3) Uani 1.00 N1 .66951(6) .36927(4) .92778(3) .0432(3) Uani 1.00 C1 .84195(7) .46150(4) .81984(3) .0365(3) Uani 1.00 C2 .80140(7) .44768(4) .91804(3) .0363(3) Uani 1.00 C3 .75404(7) .55366(4) .96073(4) .0405(3) Uani 1.00 C4 .88997(8) .63417(5) .95388(4) .0499(4) Uani 1.00 C5 .84580(10) .74627(5) .93186(6) .0815(5) Uani 1.00 C6 .71612(9) .53928(6) 1.05987(4) .0679(4) Uani 1.00 C7 .82091(7) .26836(4) .81462(3) .0359(3) Uani 1.00 C8 .68062(7) .28621(4) .87948(4) .0403(3) Uani 1.00 C9 .54188(8) .20840(5) .87675(5) .0596(4) Uani 1.00 C10 .53561(8) .15005(5) .78696(5) .0571(4) Uani 1.00 C11 .58995(8) .22898(5) .71260(5) .0553(4) Uani 1.00 C12 .76450(7) .19647(4) .73793(4) .0417(3) Uani 1.00 C13 .69283(7) .08731(4) .77030(4) .0506(3) Uani 1.00 C14 .67890(10) .01124(5) .69040(5) .0752(5) Uani 1.00 C15 .76320(10) .02463(5) .84758(5) .0745(5) Uani 1.00 C16 .98016(8) .23392(5) .85619(4) .0524(4) Uani 1.00 H2 .895698 .421476 .948537 .055864 Uiso 1.00 H12 .847900 .194369 .693132 .060903 Uiso 1.00 H3 .660136 .581655 .931029 .060233 Uiso 1.00 H10 .429805 .122954 .773059 .076141 Uiso 1.00 H16A 1.059359 .223717 .809893 .071199 Uiso 1.00 H16B .965759 .168317 .888593 .071199 Uiso 1.00 H16C 1.016460 .288617 .896493 .071199 Uiso 1.00 H11A .545850 .206181 .656304 .074133 Uiso 1.00 H11B .552050 .299681 .726004 .074133 Uiso 1.00 H9A .442577 .246401 .886650 .078735 Uiso 1.00 H9B .556677 .156501 .923350 .078735 Uiso 1.00 H6A .629518 .488680 1.066470 .085913 Uiso 1.00 H6B .684218 .606580 1.085170 .085913 Uiso 1.00 H6C .810518 .513380 1.090370 .085913 Uiso 1.00 H15A .774128 .070929 .898481 .092678 Uiso 1.00 H15B .867628 -.002871 .831281 .092678 Uiso 1.00 H15C .692428 -.033571 .862280 .092678 Uiso 1.00 H5A .942068 .789070 .928755 .099180 Uiso 1.00 H5B .775368 .774070 .977355 .099180 Uiso 1.00 H5C .791368 .747970 .875055 .099180 Uiso 1.00 H14A .634738 .048144 .639597 .093213 Uiso 1.00 H14B .608838 -.046856 .706497 .093213 Uiso 1.00 H14C .784038 -.016156 .675497 .093213 Uiso 1.00 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 .0556(2) .0347(2) .0326(2) -.0069(2) .0083(2) .0013(2) O2 .0781(3) .0368(2) .0443(2) -.0085(2) .0069(2) .0085(2) O3 .0525(3) .0817(3) .0858(3) -.0037(3) -.0124(3) -.0150(3) N1 .0519(3) .0398(3) .0379(3) -.0034(3) .0113(2) .0030(2) C1 .0389(3) .0346(3) .0361(3) -.0023(3) .0030(3) .0019(3) C2 .0437(3) .0331(3) .0321(3) .0046(3) .0022(2) .0016(2) C3 .0428(3) .0380(3) .0408(3) .0083(3) .0008(3) -.0039(3) C4 .0540(4) .0488(4) .0469(4) -.0002(3) .0051(3) -.0119(3) C5 .0864(6) .0384(4) .1198(7) -.0025(4) .0269(5) -.0088(4) C6 .0882(6) .0626(4) .0529(4) -.0023(4) .0241(4) -.0125(3) C7 .0417(3) .0307(3) .0354(3) -.0026(3) .0018(3) .0033(2) C8 .0428(3) .0403(3) .0378(3) -.0041(3) .0048(3) .0081(3) C9 .0543(4) .0520(4) .0724(5) -.0150(3) .0201(4) .0008(3) C10 .0434(4) .0534(4) .0745(5) -.0138(3) .0031(3) -.0053(4) C11 .0506(4) .0559(4) .0593(4) -.0023(3) -.0129(3) -.0047(3) C12 .0422(3) .0399(3) .0429(3) -.0047(3) .0037(3) -.0030(3) C13 .0491(4) .0380(3) .0648(4) -.0086(3) .0029(3) -.0006(3) C14 .0686(5) .0547(4) .1023(6) -.0197(4) .0043(5) -.0225(4) C15 .0819(5) .0417(4) .0998(6) -.0056(4) .0014(5) .0193(4) C16 .0511(4) .0470(4) .0591(4) .0035(3) -.0090(3) -.0060(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C ' 'C ' .0033 .0016 'Waasmaier & Kirfel, 1995' 'H ' 'H ' .0000 .0000 'Waasmaier & Kirfel, 1995' 'N ' 'N ' .0061 .0033 'Waasmaier & Kirfel, 1995' 'O ' 'O ' .0106 .0060 'Waasmaier & Kirfel, 1995' 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 O1 C7 118.60(10) yes C2 N1 C8 115.90(10) yes O1 C1 O2 119.50(10) yes O1 C1 C2 116.60(10) yes O2 C1 C2 123.80(10) yes N1 C2 C1 109.60(10) yes N1 C2 C3 110.40(10) yes C1 C2 C3 111.30(10) yes C2 C3 C4 111.20(10) yes C2 C3 C6 110.90(10) yes C4 C3 C6 107.30(10) yes O3 C4 C3 120.40(10) yes O3 C4 C5 122.00(10) yes C3 C4 C5 117.50(10) yes O1 C7 C8 106.10(10) yes O1 C7 C12 103.40(10) no O1 C7 C16 107.10(10) no C8 C7 C12 109.20(10) no C8 C7 C16 116.10(10) no C12 C7 C16 113.80(10) no N1 C8 C7 122.40(10) no N1 C8 C9 119.40(10) no C7 C8 C9 117.80(10) no C8 C9 C10 111.00(10) no C9 C10 C11 108.30(10) no C9 C10 C13 110.90(10) no C11 C10 C13 88.00(10) no C10 C11 C12 85.80(10) no C7 C12 C11 108.20(10) no C7 C12 C13 113.40(10) no C11 C12 C13 87.30(10) no C10 C13 C12 85.60(10) no C10 C13 C14 112.40(10) no C10 C13 C15 117.80(10) no C12 C13 C14 109.30(10) no C12 C13 C15 122.90(10) no C14 C13 C15 107.50(10) 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 O1 C1 . . 1.3412(6) yes O1 C7 . . 1.4772(6) yes O2 C1 . . 1.2059(6) yes O3 C4 . . 1.2108(7) yes N1 C2 . . 1.4736(7) yes N1 C8 . . 1.2687(6) yes C1 C2 . . 1.5138(7) yes C2 C3 . . 1.5228(7) yes C3 C4 . . 1.5124(8) yes C3 C6 . . 1.5235(9) yes C4 C5 . . 1.4867(9) yes C7 C8 . . 1.5266(8) yes C7 C12 . . 1.5290(7) no C7 C16 . . 1.5171(8) no C8 C9 . . 1.5046(8) no C9 C10 . . 1.5270(10) no C10 C11 . . 1.5523(9) no C10 C13 . . 1.5381(9) no C11 C12 . . 1.5453(8) no C12 C13 . . 1.5655(7) no C13 C14 . . 1.5305(9) no C13 C15 . . 1.5116(9) 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 C7 O1 C1 O2 -178.80(10) no C7 O1 C1 C2 -.90(10) no C1 O1 C7 C8 40.70(10) no C1 O1 C7 C12 155.60(10) no C1 O1 C7 C16 -83.90(10) no C8 N1 C2 C1 43.10(10) no C8 N1 C2 C3 166.00(10) no C2 N1 C8 C7 -.40(10) no C2 N1 C8 C9 -172.70(10) no O1 C1 C2 N1 -43.00(10) no O1 C1 C2 C3 -165.40(10) yes O2 C1 C2 N1 134.90(10) no O2 C1 C2 C3 12.50(10) no N1 C2 C3 C4 178.30(10) no N1 C2 C3 C6 59.00(10) no C1 C2 C3 C4 -59.80(10) yes C1 C2 C3 C6 -179.10(10) no C2 C3 C4 O3 -44.40(10) no C2 C3 C4 C5 139.20(10) no C6 C3 C4 O3 77.00(10) yes C6 C3 C4 C5 -99.40(10) no O1 C7 C8 N1 -42.00(10) no O1 C7 C8 C9 130.40(10) no O1 C7 C12 C11 -73.40(10) no O1 C7 C12 C13 -168.50(10) no C12 C7 C8 N1 -152.80(10) no C12 C7 C8 C9 19.50(10) no C8 C7 C12 C11 39.20(10) no C8 C7 C12 C13 -55.80(10) no C16 C7 C8 N1 76.80(10) no C16 C7 C8 C9 -110.80(10) no C16 C7 C12 C11 170.80(10) no C16 C7 C12 C13 75.70(10) no N1 C8 C9 C10 151.10(10) no C7 C8 C9 C10 -21.50(10) no C8 C9 C10 C11 -35.10(10) no C8 C9 C10 C13 59.90(10) no C9 C10 C11 C12 84.10(10) no C9 C10 C13 C12 -81.90(10) no C9 C10 C13 C14 169.00(10) no C9 C10 C13 C15 43.30(10) no C13 C10 C11 C12 -27.30(10) no C11 C10 C13 C12 27.00(10) no C11 C10 C13 C14 -82.10(10) no C11 C10 C13 C15 152.10(10) no C10 C11 C12 C7 -87.00(10) no C10 C11 C12 C13 26.80(10) no C7 C12 C13 C10 81.60(10) no C7 C12 C13 C14 -166.20(10) no C7 C12 C13 C15 -38.90(10) no C11 C12 C13 C10 -27.10(10) no C11 C12 C13 C14 85.10(10) no C11 C12 C13 C15 -147.60(10) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9429445 2 PubChem 11254418