#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/19/2011959.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_2011959 loop_ _publ_author_name 'Zukerman-Schpector, J.' 'Caracelli, I.' 'Vega, Mauricio' 'Constantino, Mauricio Gomes' 'Beatriz, Adilson' 'da Silva, Gil Valdo' _publ_section_title ; Two polycyclic compounds derived from a Diels--Alder reaction ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 646 _journal_page_last 648 _journal_paper_doi 10.1107/S0108270101003365 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C12 H16 O5' _chemical_formula_sum 'C12 H16 O5' _chemical_formula_weight 240.25 _chemical_name_systematic ; 5,6-dimethoxy-3,7-dioxatetracyclo[6.4.0.0^2,6^0^4,12^]dodec-9-en-11-ol ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _cell_angle_alpha 90 _cell_angle_beta 94.69(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 7.5450(10) _cell_length_b 10.7500(10) _cell_length_c 27.336(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293 _cell_measurement_theta_max 18.15 _cell_measurement_theta_min 9.90 _cell_volume 2209.8(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius,1989)' _computing_data_reduction 'XCAD-4 (Harms & Wocadlo, 1995)' _computing_molecular_graphics 'ZORTEP (Zsolnai, 1995)' _computing_publication_material 'PARST95 (Nardelli, 1995), PLATON (Spek, 1998), WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_measurement_device_type 'Enraf-Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .026 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 4326 _diffrn_reflns_theta_max 25.5 _diffrn_standards_decay_% 1.1 _diffrn_standards_interval_time 30 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .112 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_meas ? _exptl_crystal_description irregular _exptl_crystal_F_000 1024.0 _exptl_crystal_size_max .25 _exptl_crystal_size_mid .20 _exptl_crystal_size_min .16 _refine_diff_density_max .190 _refine_diff_density_min -.214 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.055 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 156 _refine_ls_number_reflns 2038 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_restrained_S_obs 1.055 _refine_ls_R_factor_all .061 _refine_ls_R_factor_gt .040 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0465P)^2^+1.8597P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .111 _refine_ls_wR_factor_ref .100 _reflns_number_gt 1513 _reflns_number_total 2038 _reflns_threshold_expression F^2^>2\sF^2^ _cod_data_source_file da1175.cif _cod_data_source_block II _cod_depositor_comments ; Automatic conversion scripts had previously changed '_atom_site_refinement_flags' tag values 'd' into 'D' as recommended by 'cif_core.dic' version 2.4.1. However, manual inspection revealed that the underlying problem was actually related to a wrong tag names inside the atom site loop. The following changes were performed to resolve the problem: * '_atom_site_refinement_flags' tag was changed to '_atom_site_calc_flag' * '_atom_site_calc_flag' tag was changed to '_atom_site_site_symmetry_order' * '_atom_site_disorder_group' tag was changed to '_atom_site_refinement_flags_posn' Antanas Vaitkus, 2015-02-19 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2011959 _cod_database_fobs_code 2011959 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .5145(2) .37746(15) .12294(6) .0487(4) Uani 1 d . 1 . . O O2 .40985(17) .06233(14) .11975(5) .0384(4) Uani 1 d . 1 . . O O3 .96747(18) .16362(17) .17533(6) .0534(5) Uani 1 d . 1 . . O H3O .9372 .1178 .1411 .064 Uiso 1 d R 1 . . H O4 .32909(16) .17881(16) .05138(5) .0432(4) Uani 1 d . 1 . . O O5 .74248(17) .10451(15) .08970(5) .0416(4) Uani 1 d . 1 . . O C1 .4723(2) .2171(2) .18084(7) .0382(5) Uani 1 d . 1 . . C H1 .4188 .2488 .2098 .046 Uiso 1 calc R 1 . . H C2 .3940(3) .2797(2) .13359(7) .0409(5) Uani 1 d . 1 . . C H2 .2692 .3049 .1337 .049 Uiso 1 calc R 1 . . H C4 .6745(3) .3031(2) .12733(8) .0426(5) Uani 1 d . 1 . . C H4 .7819 .3506 .1219 .051 Uiso 1 calc R 1 . . H C5 .6264(2) .2071(2) .08736(7) .0375(5) Uani 1 d . 1 . . C H5 .6294 .2471 .0552 .045 Uiso 1 calc R 1 . . H C6 .4300(2) .1778(2) .09652(7) .0354(5) Uani 1 d . 1 . . C C8 .4345(3) .0799(2) .17260(7) .0379(5) Uani 1 d . 1 . . C H8 .3237 .0585 .1870 .046 Uiso 1 calc R 1 . . H C9 .5782(3) -.0054(2) .19291(7) .0420(5) Uani 1 d . 1 . . C H9 .5506 -.0887 .1974 .050 Uiso 1 calc R 1 . . H C10 .7427(3) .0320(2) .20482(7) .0441(5) Uani 1 d . 1 . . C H10 .8241 -.0281 .2166 .053 Uiso 1 calc R 1 . . H C11 .8095(3) .1612(2) .20115(7) .0427(5) Uani 1 d . 1 . . C H11 .8453 .1878 .2348 .051 Uiso 1 calc R 1 . . H C12 .6707(3) .2561(2) .18038(7) .0400(5) Uani 1 d . 1 . . C H12 .6857 .3297 .2014 .048 Uiso 1 calc R 1 . . H C13 .7111(3) .0236(3) .04885(8) .0539(6) Uani 1 d . 1 . . C H13A .7997 -.0407 .0505 .081 Uiso 1 calc R 1 . . H H13B .7169 .0700 .0190 .081 Uiso 1 calc R 1 . . H H13C .5953 -.0132 .0494 .081 Uiso 1 calc R 1 . . H C14 .1424(3) .1584(3) .05426(8) .0519(6) Uani 1 d . 1 . . C H14A .0831 .1598 .0218 .078 Uiso 1 calc R 1 . . H H14B .0949 .2228 .0737 .078 Uiso 1 calc R 1 . . H H14C .1244 .0791 .0692 .078 Uiso 1 calc R 1 . . 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 O1 .0493(9) .0391(9) .0568(9) .0008(7) -.0013(7) .0039(7) O2 .0425(8) .0446(9) .0275(7) -.0091(7) -.0008(5) .0011(6) O3 .0306(7) .0782(13) .0509(9) -.0031(8) .0001(6) -.0055(8) O4 .0293(7) .0698(11) .0298(7) -.0035(7) -.0028(5) .0050(7) O5 .0311(7) .0576(10) .0353(7) .0040(7) -.0015(5) -.0042(7) C1 .0343(10) .0497(13) .0304(10) .0031(9) .0023(8) -.0057(9) C2 .0339(10) .0476(14) .0410(11) .0034(9) .0021(8) -.0002(10) C4 .0347(10) .0444(13) .0477(12) -.0075(9) -.0022(8) .0029(10) C5 .0311(10) .0489(13) .0323(10) -.0024(9) .0016(7) .0064(9) C6 .0294(9) .0469(13) .0292(9) -.0019(9) -.0019(7) .0055(9) C8 .0345(10) .0521(14) .0273(9) -.0042(9) .0031(7) .0017(9) C9 .0474(12) .0442(13) .0344(10) -.0013(10) .0029(8) .0078(9) C10 .0449(12) .0539(15) .0326(10) .0095(10) -.0029(8) .0041(10) C11 .0350(10) .0599(15) .0319(10) .0020(10) -.0046(8) -.0071(10) C12 .0384(10) .0423(13) .0384(11) -.0029(9) -.0025(8) -.0101(9) C13 .0531(13) .0686(18) .0393(12) .0112(12) -.0012(9) -.0111(12) C14 .0316(10) .0800(19) .0427(12) -.0059(11) -.0053(9) .0036(12) 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 '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 C2 O1 C4 96.72(15) yes C6 O2 C8 108.91(15) yes C6 O4 C14 114.67(15) yes C5 O5 C13 112.42(15) yes C8 C1 C2 104.31(16) no C8 C1 C12 115.46(17) no C2 C1 C12 100.39(16) no O1 C2 C1 106.58(16) yes O1 C2 C6 103.88(16) yes C1 C2 C6 99.60(17) yes O1 C4 C5 99.60(15) yes O1 C4 C12 100.40(16) yes C5 C4 C12 115.55(18) yes O5 C5 C4 112.80(15) no O5 C5 C6 115.55(17) no C4 C5 C6 101.29(16) no O4 C6 O2 109.54(16) no O4 C6 C2 117.74(17) no O2 C6 C2 107.49(15) no O4 C6 C5 108.31(15) no O2 C6 C5 113.01(16) no C2 C6 C5 100.63(16) no O2 C8 C9 108.69(16) no O2 C8 C1 106.33(16) no C9 C8 C1 114.86(16) no C10 C9 C8 123.0(2) yes C9 C10 C11 125.9(2) yes O3 C11 C10 110.56(18) no O3 C11 C12 111.99(18) no C10 C11 C12 114.92(17) no C11 C12 C4 120.12(17) no C11 C12 C1 116.46(18) no C4 C12 C1 100.85(15) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C2 1.435(3) yes O1 C4 1.444(3) yes O2 C6 1.408(2) yes O2 C8 1.454(2) yes O3 C11 1.434(2) no O4 C6 1.396(2) no O4 C14 1.434(2) no O5 C5 1.406(3) no O5 C13 1.420(3) no C1 C8 1.516(3) no C1 C2 1.531(3) no C1 C12 1.555(3) no C2 C6 1.532(3) no C4 C5 1.525(3) no C4 C12 1.538(3) no C5 C6 1.555(2) no C8 C9 1.492(3) no C9 C10 1.319(3) yes C10 C11 1.483(3) no C11 C12 1.537(3) no 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 _geom_hbond_publ_flag O3 H3O O5 1_555 1.06 1.95 2.849(2) 140 yes C13 H13C O2 1_555 .96 2.60 3.133(3) 115 yes C13 H13A O1 3_545 .96 2.61 3.325(3) 132 yes C4 H4 O2 3_555 .98 2.47 3.320(3) 144 yes C11 H11 O3 2_755 .98 2.74 3.648(3) 154 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135272 2 PubChem 11831536