#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/14/2011410.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_2011410 loop_ _publ_author_name 'Gerrard, Juliet A.' 'Meade, Susie J.' 'Morris, Jonathan C.' 'Steel, Peter J.' _publ_section_title ; Two crystalline modifications of 2-hydroxycyclopent-2-enone ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1251 _journal_page_last 1253 _journal_paper_doi 10.1107/S0108270100009550 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C5 H6 O2' _chemical_formula_sum 'C5 H6 O2' _chemical_formula_weight 98.10 _chemical_name_common 3-Hydroxycyclopent-2-enone _chemical_name_systematic ; 3-Hydroxycyclopent-2-enone ; _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 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.370(5) _cell_length_b 8.971(8) _cell_length_c 9.920(9) _cell_measurement_reflns_used 1694 _cell_measurement_temperature 163(2) _cell_measurement_theta_max 25.0 _cell_measurement_theta_min 3.1 _cell_volume 477.9(8) _computing_cell_refinement 'SAINT (Siemens 1999)' _computing_data_collection 'SMART (Siemens 1999)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXL97 _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 163(2) _diffrn_detector_area_resol_mean 8.19 _diffrn_measured_fraction_theta_full .989 _diffrn_measured_fraction_theta_max .989 _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method 'Exposures over 0.5\% \f or \w rotation' _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 .0325 _diffrn_reflns_av_sigmaI/netI .0322 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5395 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 3.06 _diffrn_standards_decay_% 0 _exptl_absorpt_coefficient_mu .106 _exptl_absorpt_correction_T_max .968 _exptl_absorpt_correction_T_min .806 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Siemens, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 208 _exptl_crystal_size_max .68 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .01 _refine_diff_density_max .116 _refine_diff_density_min -.161 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -.4(18) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref .977 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 67 _refine_ls_number_reflns 835 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .977 _refine_ls_R_factor_all .0451 _refine_ls_R_factor_gt .0315 _refine_ls_shift/su_max .001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0411P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .0697 _reflns_number_gt 674 _reflns_number_total 835 _reflns_threshold_expression I>2\s(I) _cod_data_source_file de1148.cif _cod_data_source_block 3sm1 _cod_original_sg_symbol_H-M 'P21 21 21' _cod_database_code 2011410 _cod_database_fobs_code 2011410 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 O1 .4244(2) .81562(13) .55387(12) .0402(4) Uani d . 1 . . O C1 .4856(3) .92964(18) .49219(18) .0328(5) Uani d . 1 . . C O2 .1665(2) .90991(14) .31264(12) .0390(4) Uani d . 1 . . O H2 .127(4) .834(2) .362(2) .047 Uiso d . 1 . . H C2 .3634(3) .98241(19) .36880(18) .0305(4) Uani d . 1 . . C C3 .4726(3) 1.10732(19) .32288(19) .0347(5) Uani d . 1 . . C H3 .4191 1.1607 .2454 .042 Uiso calc R 1 . . H C4 .6891(4) 1.15175(19) .40908(18) .0376(5) Uani d . 1 . . C H4A .6671 1.2542 .4442 .045 Uiso calc R 1 . . H H4B .8465 1.1471 .3573 .045 Uiso calc R 1 . . H C5 .6902(4) 1.03691(18) .52556(18) .0369(5) Uani d . 1 . . C H5A .8526 .9849 .5305 .044 Uiso calc R 1 . . H H5B .6580 1.0865 .6130 .044 Uiso 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 .0421(9) .0328(7) .0457(8) .0019(6) .0011(6) .0106(6) C1 .0331(12) .0292(9) .0362(10) .0074(8) .0038(9) -.0027(9) O2 .0459(9) .0319(7) .0392(7) -.0053(7) -.0047(7) .0056(6) C2 .0322(11) .0274(9) .0317(9) .0046(8) .0013(8) -.0043(8) C3 .0402(12) .0291(10) .0348(10) .0024(9) .0034(9) .0023(8) C4 .0426(13) .0278(9) .0423(11) .0000(10) .0023(9) .0027(7) C5 .0377(12) .0339(9) .0390(11) .0009(9) .0006(10) .0000(8) 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' H H .0000 .0000 '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' 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 O1 C1 C2 124.13(17) yes O1 C1 C5 128.10(17) yes C2 C1 C5 107.77(15) yes C2 O2 H2 109.6(13) yes C3 C2 O2 126.77(19) yes C3 C2 C1 110.90(18) yes O2 C2 C1 122.33(16) yes C2 C3 C4 111.53(17) yes C2 C3 H3 124.2 ? C4 C3 H3 124.2 ? C3 C4 C5 104.61(15) yes C3 C4 H4A 110.8 ? C5 C4 H4A 110.8 ? C3 C4 H4B 110.8 ? C5 C4 H4B 110.8 ? H4A C4 H4B 108.9 ? C1 C5 C4 105.05(15) yes C1 C5 H5A 110.7 ? C4 C5 H5A 110.7 ? C1 C5 H5B 110.7 ? C4 C5 H5B 110.7 ? H5A C5 H5B 108.8 ? 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 . 1.236(2) yes C1 C2 . 1.467(3) yes C1 C5 . 1.498(3) yes O2 C2 . 1.361(2) yes O2 H2 . .87(2) yes C2 C3 . 1.344(3) yes C3 C4 . 1.497(3) yes C3 H3 . .9500 ? C4 C5 . 1.548(3) yes C4 H4A . .9900 ? C4 H4B . .9900 ? C5 H5A . .9900 ? C5 H5B . .9900 ? 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 H2 O1 4_466 .87(2) 1.92(2) 2.745(2) 159.5(18) 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 -178.77(17) C5 C1 C2 C3 .93(19) O1 C1 C2 O2 1.2(3) C5 C1 C2 O2 -179.14(15) O2 C2 C3 C4 -178.30(15) C1 C2 C3 C4 1.6(2) C2 C3 C4 C5 -3.40(19) O1 C1 C5 C4 176.75(17) C2 C1 C5 C4 -2.93(18) C3 C4 C5 C1 3.72(18) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 74607