#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/37/2003709.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_2003709 loop_ _publ_author_name 'Alvarez-Larena, A.' 'Piniella, J. F.' 'Cid, P.' 'de March, P.' 'Figueredo, M.' 'Font, J.' 'Mil\'an, S.' 'Soria, A.' _publ_section_title ; Three Lactone Fused Perhydroisoxazolo[2,3-a]pyridines: a Conformational Study ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1314 _journal_page_last 1319 _journal_paper_doi 10.1107/S0108270194013661 _journal_volume 51 _journal_year 1995 _chemical_formula_sum 'C10 H15 N O3' _chemical_formula_weight 197.23 _chemical_name_systematic ; (4aRS,10aRS,10bRS)-Octahydro-1H,3H-pyrano[3',4':4,5]isoxazolo[2,3-a]pyridin- 1-one. ; _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.765(3) _cell_length_b 8.930(2) _cell_length_c 16.166(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.10 _cell_measurement_theta_min 9.94 _cell_volume 976.6(6) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1994).' _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method '\w/2\q scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.70926 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0201 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 1023 _diffrn_reflns_theta_max 24.95 _diffrn_reflns_theta_min 2.51 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.341 _exptl_crystal_description prism _exptl_crystal_F_000 424 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.116 _refine_diff_density_min -0.092 _refine_ls_abs_structure_Flack 1.37(185) _refine_ls_extinction_coef 0.038(4) _refine_ls_extinction_method 'SHELXL93 (Sheldrick, 1993)' _refine_ls_goodness_of_fit_all 1.088 _refine_ls_goodness_of_fit_obs 1.089 _refine_ls_hydrogen_treatment refU _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1023 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.088 _refine_ls_restrained_S_obs 1.089 _refine_ls_R_factor_all 0.0373 _refine_ls_R_factor_obs 0.0281 _refine_ls_shift/esd_max 0.117 _refine_ls_shift/esd_mean 0.034 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme ;calc w = 1/[\s^2^(Fo^2^) + (0.0392P)^2^ + 0.1142P] where P = (Fo^2^ + 2Fc^2^)/3 ; _refine_ls_wR_factor_all 0.0779 _refine_ls_wR_factor_obs 0.0719 _reflns_number_observed 889 _reflns_number_total 1023 _reflns_observed_criterion >2sigma(I) _cod_data_source_file na1129.cif _cod_data_source_block 3b _cod_database_code 2003709 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_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 C1 0.0353(11) 0.0093(10) 0.0018(11) 0.0493(12) 0.0072(11) 0.0522(12) O2 0.0363(7) -0.0061(8) 0.0018(8) 0.0676(10) 0.0061(8) 0.0477(9) N3 0.0368(9) 0.0017(9) 0.0050(8) 0.0475(9) 0.0005(8) 0.0426(9) C4 0.0553(14) -0.0015(12) 0.0082(12) 0.0548(13) 0.0071(11) 0.0454(11) C5 0.067(2) 0.0045(14) 0.0004(12) 0.0541(13) -0.0003(11) 0.0431(11) C6 0.0527(14) 0.0014(14) -0.0101(13) 0.0638(14) -0.0076(13) 0.0539(13) C7 0.0407(11) -0.0052(12) 0.0013(11) 0.0632(14) -0.0061(11) 0.0495(12) C8 0.0358(10) 0.0019(10) 0.0042(9) 0.0388(10) -0.0029(10) 0.0416(10) C9 0.0411(12) 0.0011(10) 0.0026(10) 0.0382(10) 0.0047(9) 0.0441(11) C10 0.0421(12) 0.0033(12) -0.0009(10) 0.0511(12) 0.0065(10) 0.0404(11) O11 0.0469(10) -0.0127(10) 0.0137(9) 0.0831(12) 0.0033(9) 0.0589(10) O12 0.0517(10) 0.0032(8) 0.0054(7) 0.0580(9) -0.0033(8) 0.0460(8) C13 0.0525(14) -0.0053(12) -0.0069(11) 0.0522(12) -0.0023(11) 0.0505(12) C14 0.0409(13) -0.0004(11) -0.0091(11) 0.0649(15) 0.0091(12) 0.0524(12) loop_ _atom_site_label _atom_site_occupancy _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol C1 1 1.0217(3) 0.4251(3) 0.69251(14) 0.0456(5) Uani d . C H1 1 0.9429(3) 0.5171(3) 0.69152(14) 0.062(2) Uiso calc R H O2 1 0.9926(2) 0.3477(2) 0.77030(9) 0.0505(4) Uani d . O N3 1 1.1418(3) 0.4166(2) 0.82334(10) 0.0423(4) Uani d . N C4 1 1.1550(4) 0.3327(3) 0.90031(13) 0.0518(6) Uani d . C H4A 1 1.1798(4) 0.2277(3) 0.88908(13) 0.062(2) Uiso calc R H H4B 1 1.0327(4) 0.3411(3) 0.93127(13) 0.062(2) Uiso calc R H C5 1 1.3242(4) 0.3996(3) 0.94871(13) 0.0548(6) Uani d . C H5A 1 1.3397(4) 0.3455(3) 1.00032(13) 0.062(2) Uiso calc R H H5B 1 1.2938(4) 0.5030(3) 0.96191(13) 0.062(2) Uiso calc R H C6 1 1.5166(4) 0.3932(3) 0.90044(14) 0.0568(6) Uani d . C H6A 1 1.5563(4) 0.2897(3) 0.89319(14) 0.062(2) Uiso calc R H H6B 1 1.6197(4) 0.4442(3) 0.93120(14) 0.062(2) Uiso calc R H C7 1 1.4916(3) 0.4673(3) 0.81588(14) 0.0511(6) Uani d . C H7A 1 1.4694(3) 0.5739(3) 0.82268(14) 0.062(2) Uiso calc R H H7B 1 1.6105(3) 0.4535(3) 0.78321(14) 0.062(2) Uiso calc R H C8 1 1.3179(3) 0.3972(2) 0.77246(12) 0.0388(5) Uani d . C H8 1 1.3431(3) 0.2900(2) 0.76485(12) 0.062(2) Uiso calc R H C9 1 1.2452(3) 0.4642(2) 0.69079(13) 0.0411(5) Uani d . C H9 1 1.2596(3) 0.5733(2) 0.69336(13) 0.062(2) Uiso calc R H C10 1 1.3622(3) 0.4068(3) 0.61850(12) 0.0445(5) Uani d . C O11 1 1.5132(2) 0.4656(2) 0.59598(11) 0.0630(5) Uani d . O O12 1 1.3015(3) 0.2834(2) 0.57936(9) 0.0519(4) Uani d . O C13 1 1.1174(4) 0.2108(3) 0.60451(14) 0.0517(6) Uani d . C H13A 1 1.1411(4) 0.1503(3) 0.65336(14) 0.062(2) Uiso calc R H H13B 1 1.0724(4) 0.1450(3) 0.56065(14) 0.062(2) Uiso calc R H C14 1 0.9605(4) 0.3245(3) 0.62289(15) 0.0527(6) Uani d . C H14A 1 0.9358(4) 0.3841(3) 0.57383(15) 0.062(2) Uiso calc R H H14B 1 0.8387(4) 0.2736(3) 0.63749(15) 0.062(2) Uiso calc R H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_source _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag C C 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0033 0.001 H H 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0000 0.000 N N 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0061 0.003 O O 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 0.0106 0.006 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 O2 C1 C14 109.2(2) y O2 C1 C9 104.8(2) y C14 C1 C9 113.0(2) y C1 O2 N3 102.40(10) y C4 N3 C8 111.7(2) y C4 N3 O2 109.1(2) y C8 N3 O2 100.60(10) y N3 C4 C5 106.6(2) y C4 C5 C6 111.6(2) y C5 C6 C7 110.4(2) y C8 C7 C6 108.9(2) y N3 C8 C7 109.0(2) y N3 C8 C9 100.2(2) y C7 C8 C9 119.4(2) y C10 C9 C8 111.6(2) y C10 C9 C1 116.8(2) y C8 C9 C1 102.1(2) y O11 C10 O12 118.5(2) y O11 C10 C9 122.2(2) y O12 C10 C9 119.2(2) y C10 O12 C13 119.8(2) y O12 C13 C14 111.0(2) y C1 C14 C13 111.1(2) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 O2 1.448(3) y C1 C14 1.498(3) y C1 C9 1.552(3) y O2 N3 1.460(2) y N3 C4 1.456(3) y N3 C8 1.458(3) y C4 C5 1.510(3) y C5 C6 1.519(3) y C6 C7 1.528(3) y C7 C8 1.505(3) y C8 C9 1.531(3) y C9 C10 1.502(3) y C10 O11 1.205(3) y C10 O12 1.336(3) y O12 C13 1.462(3) y C13 C14 1.499(4) y loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10317795 2 PubChem 21728348