#------------------------------------------------------------------------------ #$Date: 2016-02-19 14:29:56 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176759 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/71/2007133.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_2007133 loop_ _publ_author_name 'Fayle, Si\^an E.' 'Gerrard, Juliet A.' 'Nursten, Harry E.' 'Steel, Peter J.' _publ_section_title ; Cyclotene Hydrate, C~6~H~8~O~2~.H~2~O ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 404 _journal_page_last 405 _journal_paper_doi 10.1107/S0108270197013632 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C6 H8 O2, H2 O' _chemical_formula_sum 'C6 H10 O3' _chemical_formula_weight 130.14 _chemical_name_common 'cyclotene hydrate' _chemical_name_systematic '2-Hydroxy-3-methylcyclopent-2-enone hydrate' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method SHELXL _cell_angle_alpha 111.5290(10) _cell_angle_beta 95.615(2) _cell_angle_gamma 106.786(2) _cell_formula_units_Z 2 _cell_length_a 6.8829(2) _cell_length_b 6.9979(3) _cell_length_c 7.8655(3) _cell_measurement_reflns_used 3259 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 26.44 _cell_measurement_theta_min 2.86 _cell_volume 328.45(2) _computing_cell_refinement 'SAINT (Siemens 1995)' _computing_data_collection 'SMART (Siemens 1995)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXL93 _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 153(2) _diffrn_detector_area_resol_mean 8.19 _diffrn_measured_fraction_theta_max 0.926 _diffrn_measurement_device 'Siemens SMART CCD' _diffrn_measurement_method 'Exposures over 0.3\% \f or \w rotation' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_sigmaI/netI 0.0337 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 3259 _diffrn_reflns_theta_max 26.44 _diffrn_reflns_theta_min 2.86 _diffrn_standards_decay_% 0 _diffrn_standards_number no _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.316 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 140 _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.39 _refine_diff_density_max 0.223 _refine_diff_density_min -0.234 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.135 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 92 _refine_ls_number_reflns 1258 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.135 _refine_ls_restrained_S_obs 1.153 _refine_ls_R_factor_gt 0.0445 _refine_ls_shift/esd_mean 0.000 _refine_ls_shift/su_max -0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ' w = 1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.1170P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.1156 _reflns_number_gt 1152 _reflns_number_total 1258 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ta1197.cif _cod_data_source_block cyclotene _cod_database_code 2007133 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -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_group _atom_site_type_symbol O1 .3429(2) .7178(2) 1.28819(15) .0322(3) Uani d . 1 . O O2 .3398(2) .7767(2) .9591(2) .0297(3) Uani d . 1 . O H21 .361(3) .774(3) .852(3) .044 Uiso d . 1 . H C1 .2764(2) .5590(3) 1.1355(2) .0248(4) Uani d . 1 . C C2 .2698(2) .5736(2) .9553(2) .0226(3) Uani d . 1 . C C3 .1879(2) .3735(3) .8132(2) .0255(4) Uani d . 1 . C C4 .1304(3) .1988(3) .8854(2) .0319(4) Uani d . 1 . C H4A .2094(3) .0986(3) .8438(2) .038 Uiso calc R 1 . H H4B -.0205(3) .1120(3) .8399(2) .038 Uiso calc R 1 . H C5 .1879(2) .3217(3) 1.0997(2) .0296(4) Uani d . 1 . C H5A .0631(2) .2927(3) 1.1522(2) .036 Uiso calc R 1 . H H5B .2924(2) .2773(3) 1.1562(2) .036 Uiso calc R 1 . H C6 .1513(3) .3193(3) .6083(2) .0345(4) Uani d . 1 . C H6A .0026(4) .2391(19) .5501(4) .052 Uiso calc R 1 . H H6B .2316(16) .2282(18) .5503(4) .052 Uiso calc R 1 . H H6C .1956(19) .4552(3) .5898(2) .052 Uiso calc R 1 . H O3 .4527(2) .8392(2) .6698(2) .0380(4) Uani d . 1 . O H31 .520(4) .980(4) .703(3) .057 Uiso d . 1 . H H32 .406(4) .783(4) .550(4) .057 Uiso d . 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 .0383(7) .0338(7) .0190(6) .0048(5) .0036(5) .0120(5) O2 .0416(7) .0231(6) .0186(6) .0022(5) .0079(5) .0094(5) C1 .0221(7) .0302(9) .0232(8) .0082(6) .0043(6) .0131(7) C2 .0223(7) .0244(8) .0214(8) .0063(6) .0052(5) .0110(6) C3 .0239(7) .0267(8) .0249(8) .0083(6) .0057(6) .0101(7) C4 .0364(9) .0229(8) .0355(9) .0098(7) .0068(7) .0121(7) C5 .0312(8) .0316(9) .0334(9) .0118(7) .0072(6) .0208(7) C6 .0393(9) .0309(9) .0223(8) .0055(7) .0053(7) .0048(7) O3 .0600(8) .0272(7) .0177(6) .0025(6) .0061(5) .0102(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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' O O 0.0106 0.0060 '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 O2 H21 112.0(14) ? O1 C1 C2 124.30(14) yes O1 C1 C5 127.38(14) yes C2 C1 C5 108.32(13) yes C3 C2 O2 132.23(14) yes C3 C2 C1 110.82(14) yes O2 C2 C1 116.94(13) yes C2 C3 C6 127.21(15) yes C2 C3 C4 110.99(14) yes C6 C3 C4 121.80(13) yes C3 C4 C5 105.34(13) yes C3 C4 H4A 110.68(8) ? C5 C4 H4A 110.68(8) ? C3 C4 H4B 110.68(9) ? C5 C4 H4B 110.68(9) ? H4A C4 H4B 108.8 ? C1 C5 C4 104.53(13) yes C1 C5 H5A 110.85(8) ? C4 C5 H5A 110.85(9) ? C1 C5 H5B 110.85(8) ? C4 C5 H5B 110.85(8) ? H5A C5 H5B 108.9 ? C3 C6 H6A 109.47(9) ? C3 C6 H6B 109.47(9) ? H6A C6 H6B 109.5 ? C3 C6 H6C 109.47(9) ? H6A C6 H6C 109.5 ? H6B C6 H6C 109.5 ? H31 O3 H32 106.(2) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.227(2) yes O2 C2 . 1.350(2) yes O2 H21 . .86(2) yes C1 C2 . 1.456(2) yes C1 C5 . 1.499(2) yes C2 C3 . 1.342(2) yes C3 C6 . 1.491(2) yes C3 C4 . 1.499(2) yes C4 C5 . 1.531(2) yes C4 H4A . .99 ? C4 H4B . .99 ? C5 H5A . .99 ? C5 H5B . .99 ? C6 H6A . .98 ? C6 H6B . .98 ? C6 H6C . .98 ? O3 H31 . .88(3) yes O3 H32 . .86(3) yes 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 O2 H21 O3 . 0.86(2) 1.78(2) 2.618(2) 165.0(10) yes O3 H31 O1 2_677 0.88(2) 2.02(2) 2.888(2) 166.0(10) yes O3 H32 O1 1_554 0.86(2) 1.91(2) 2.760(2) 167.0(10) yes 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 O1 C1 C2 C3 -179.57(14) C5 C1 C2 C3 0.0(2) O1 C1 C2 O2 -0.9(2) C5 C1 C2 O2 178.69(12) O2 C2 C3 C6 0.4(3) C1 C2 C3 C6 178.85(14) O2 C2 C3 C4 -178.78(15) C1 C2 C3 C4 -0.3(2) C2 C3 C4 C5 0.5(2) C6 C3 C4 C5 -178.70(14) O1 C1 C5 C4 179.89(14) C2 C1 C5 C4 0.3(2) C3 C4 C5 C1 -0.5(2)