#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011313.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_2011313 loop_ _publ_author_name 'Newman, Jacob M.' 'Thompson, Hugh W.' 'Lalancette, Roger A.' _publ_section_title ;Two diastereomers of (+-)-cis-2-(3-oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)cyclohexanecarboxylic acid ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1152 _journal_page_last 1154 _journal_paper_doi 10.1107/S0108270100008477 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C15 H20 O4' _chemical_formula_sum 'C15 H20 O4' _chemical_formula_weight 264.32 _chemical_melting_point 474(2) _chemical_name_systematic ; (+-)-cis-2-(3-Oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)- cyclohexanecarboxylic acid ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 91.11(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.372(7) _cell_length_b 10.467(9) _cell_length_c 11.901(16) _cell_measurement_reflns_used 41 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.72 _cell_measurement_theta_min 1.71 _cell_volume 1416(2) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXL97 _computing_publication_material SHELXL97 _computing_structure_refinement SHELXL97 _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2\q/\q scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .025 _diffrn_reflns_av_sigmaI/netI .051 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3242 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.59 _diffrn_standards_decay_% 'variation < 3.0' _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .089 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 568 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .30 _exptl_crystal_size_min .25 _refine_diff_density_max .42 _refine_diff_density_min -.32 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 2498 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.09 _refine_ls_R_factor_all .131 _refine_ls_R_factor_gt .065 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0941P)^2^+0.6553P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .237 _reflns_number_gt 1151 _reflns_number_total 2498 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1276.cif _cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '472-476' was changed to '474(2)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '472-476' was changed to '474(2)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2011313 _cod_database_fobs_code 2011313 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .5226(3) .7519(4) .5555(3) .1007(11) Uani d . 1 . . O O2 .6491(2) .6445(3) .4484(2) .0717(8) Uani d . 1 . . O O3 .8875(2) .4831(3) .4112(3) .0849(9) Uani d . 1 . . O O4 .9972(3) .6557(3) .4385(3) .0884(10) Uani d . 1 . . O C1 .6439(3) .5640(4) .3489(3) .0614(10) Uani d . 1 . . C C3 .5380(3) .6856(4) .4745(3) .0701(11) Uani d . 1 . . C C3A .4564(3) .6343(4) .3910(3) .0637(10) Uani d . 1 . . C C4 .3269(3) .6592(5) .3855(4) .0858(13) Uani d . 1 . . C C5 .2799(5) .6207(9) .2736(6) .151(3) Uani d . 1 . . C C6 .3251(5) .5033(6) .2291(6) .129(2) Uani d . 1 . . C C7A .5148(3) .5630(4) .3177(3) .0632(10) Uani d . 1 . . C C7 .4592(4) .4927(4) .2213(4) .0815(13) Uani d . 1 . . C C8 .7280(3) .6140(4) .2594(3) .0640(10) Uani d . 1 . . C C9 .8393(3) .6770(4) .3083(3) .0619(10) Uani d . 1 . . C C10 .9204(4) .7220(4) .2126(4) .0837(13) Uani d . 1 . . C C11 .9509(4) .6126(5) .1344(4) .1010(16) Uani d . 1 . . C C12 .8406(5) .5556(6) .0836(4) .1101(18) Uani d . 1 . . C C13 .7563(4) .5088(4) .1740(3) .0832(13) Uani d . 1 . . C C14 .9083(3) .5958(4) .3896(3) .0645(10) Uani d . 1 . . C H1 .6678 .4772 .3701 .074 Uiso calc R 1 . . H H4 1.044(3) .593(4) .498(3) .080 Uiso d . 1 . . H H4A .2881 .6109 .4437 .103 Uiso calc R 1 . . H H4B .3118 .7493 .3979 .103 Uiso calc R 1 . . H H5A .1951 .6131 .2781 .181 Uiso calc R 1 . . H H5B .2962 .6886 .2207 .181 Uiso calc R 1 . . H H6A .2913 .4911 .1544 .155 Uiso calc R 1 . . H H6B .2976 .4337 .2756 .155 Uiso calc R 1 . . H H7A .4826 .4036 .2237 .098 Uiso calc R 1 . . H H7B .4849 .5289 .1509 .098 Uiso calc R 1 . . H H8A .6852 .6807 .2177 .077 Uiso calc R 1 . . H H9A .8146 .7535 .3490 .074 Uiso calc R 1 . . H H10A .8813 .7890 .1698 .100 Uiso calc R 1 . . H H10B .9923 .7573 .2451 .100 Uiso calc R 1 . . H H11A 1.0007 .6439 .0751 .121 Uiso calc R 1 . . H H11B .9941 .5475 .1760 .121 Uiso calc R 1 . . H H12A .8614 .4844 .0357 .132 Uiso calc R 1 . . H H12B .8011 .6192 .0372 .132 Uiso calc R 1 . . H H13A .7915 .4367 .2133 .100 Uiso calc R 1 . . H H13B .6838 .4797 .1382 .100 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 .094(2) .119(3) .089(2) -.0041(19) .0186(17) -.031(2) O2 .0554(14) .097(2) .0625(15) -.0054(14) -.0015(12) -.0066(14) O3 .0748(19) .0740(19) .105(2) .0019(16) -.0281(16) .0185(17) O4 .0767(19) .0802(19) .107(2) -.0083(16) -.0293(17) .0167(17) C1 .060(2) .068(2) .057(2) .0058(19) -.0041(16) -.0042(18) C3 .064(2) .074(3) .072(2) -.003(2) .007(2) -.002(2) C3A .054(2) .064(2) .073(2) -.0038(19) -.0023(18) .008(2) C4 .054(2) .101(3) .102(3) .000(2) -.002(2) .023(3) C5 .067(3) .210(8) .175(6) .019(4) -.041(4) -.019(6) C6 .091(4) .129(5) .165(6) -.019(4) -.055(4) -.023(4) C7A .060(2) .059(2) .070(2) -.0066(19) -.0123(18) .0085(19) C7 .086(3) .071(3) .086(3) -.012(2) -.025(2) -.003(2) C8 .059(2) .076(2) .057(2) .0153(19) -.0013(16) .0016(19) C9 .057(2) .066(2) .062(2) .0115(18) .0054(17) .0067(18) C10 .074(3) .090(3) .087(3) .018(2) .015(2) .023(2) C11 .089(3) .130(4) .085(3) .033(3) .027(3) .022(3) C12 .122(4) .144(5) .064(3) .041(4) .011(3) -.010(3) C13 .086(3) .092(3) .072(3) .020(3) -.004(2) -.017(2) C14 .054(2) .074(3) .065(2) .011(2) .0003(18) .003(2) 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 C3 O2 C1 110.0(3) ? O2 C1 C7A 103.2(3) ? O2 C1 C8 110.6(3) ? C7A C1 C8 116.6(3) ? O1 C3 O2 120.7(4) ? O1 C3 C3A 131.4(4) ? O2 C3 C3A 107.9(3) ? C7A C3A C3 109.6(3) ? C7A C3A C4 124.8(4) ? C3 C3A C4 125.6(4) ? C5 C4 C3A 109.2(4) ? C6 C5 C4 116.0(5) ? C5 C6 C7 116.6(5) ? C3A C7A C7 124.7(4) ? C3A C7A C1 109.3(3) ? C7 C7A C1 126.0(4) ? C7A C7 C6 108.9(4) ? C9 C8 C13 112.2(3) ? C9 C8 C1 113.8(3) ? C13 C8 C1 110.8(3) ? C14 C9 C8 114.8(3) ? C14 C9 C10 109.6(3) ? C8 C9 C10 110.5(3) ? C11 C10 C9 111.5(4) ? C12 C11 C10 110.3(4) ? C11 C12 C13 111.8(4) ? C12 C13 C8 112.2(4) ? O3 C14 O4 120.9(4) ? O3 C14 C9 125.3(4) y O4 C14 C9 113.8(4) y C14 O4 H4 111(2) ? O2 C1 H1 108.7 ? C7A C1 H1 108.7 ? C8 C1 H1 108.7 ? C5 C4 H4A 109.8 ? C3A C4 H4A 109.8 ? C5 C4 H4B 109.8 ? C3A C4 H4B 109.8 ? H4A C4 H4B 108.3 ? C6 C5 H5A 108.3 ? C4 C5 H5A 108.3 ? C6 C5 H5B 108.3 ? C4 C5 H5B 108.3 ? H5A C5 H5B 107.4 ? C5 C6 H6A 108.1 ? C7 C6 H6A 108.1 ? C5 C6 H6B 108.1 ? C7 C6 H6B 108.1 ? H6A C6 H6B 107.3 ? C7A C7 H7A 109.9 ? C6 C7 H7A 109.9 ? C7A C7 H7B 109.9 ? C6 C7 H7B 109.9 ? H7A C7 H7B 108.3 ? C9 C8 H8A 106.5 ? C13 C8 H8A 106.5 ? C1 C8 H8A 106.5 ? C14 C9 H9A 107.2 ? C8 C9 H9A 107.2 ? C10 C9 H9A 107.2 ? C11 C10 H10A 109.3 ? C9 C10 H10A 109.3 ? C11 C10 H10B 109.3 ? C9 C10 H10B 109.3 ? H10A C10 H10B 108.0 ? C12 C11 H11A 109.6 ? C10 C11 H11A 109.6 ? C12 C11 H11B 109.6 ? C10 C11 H11B 109.6 ? H11A C11 H11B 108.1 ? C11 C12 H12A 109.2 ? C13 C12 H12A 109.2 ? C11 C12 H12B 109.2 ? C13 C12 H12B 109.2 ? H12A C12 H12B 107.9 ? C12 C13 H13A 109.2 ? C8 C13 H13A 109.2 ? C12 C13 H13B 109.2 ? C8 C13 H13B 109.2 ? H13A C13 H13B 107.9 ? 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 C3 . 1.203(5) ? O2 C3 . 1.375(5) ? O2 C1 . 1.454(4) ? O3 C14 . 1.231(5) y O4 C14 . 1.315(5) y C1 C7A . 1.508(5) ? C1 C8 . 1.537(5) ? C3 C3A . 1.449(6) ? C3A C7A . 1.334(5) ? C3A C4 . 1.496(5) ? C4 C5 . 1.482(8) ? C5 C6 . 1.436(8) ? C6 C7 . 1.534(7) ? C7A C7 . 1.493(5) ? C8 C9 . 1.532(5) ? C8 C13 . 1.536(5) ? C9 C14 . 1.498(5) ? C9 C10 . 1.552(5) ? C10 C11 . 1.520(6) ? C11 C12 . 1.506(7) ? C12 C13 . 1.535(6) ? O4 H4 . 1.09(4) ? C1 H1 . .9800 ? C4 H4A . .9700 ? C4 H4B . .9700 ? C5 H5A . .9700 ? C5 H5B . .9700 ? C6 H6A . .9700 ? C6 H6B . .9700 ? C7 H7A . .9700 ? C7 H7B . .9700 ? C8 H8A . .9800 ? C9 H9A . .9800 ? C10 H10A . .9700 ? C10 H10B . .9700 ? C11 H11A . .9700 ? C11 H11B . .9700 ? C12 H12A . .9700 ? C12 H12B . .9700 ? C13 H13A . .9700 ? C13 H13B . .9700 ? 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 C3 O2 C1 C7A .6(4) C3 O2 C1 C8 125.9(3) C1 O2 C3 O1 178.8(4) C1 O2 C3 C3A -.9(4) O1 C3 C3A C7A -178.7(4) O2 C3 C3A C7A .9(4) O1 C3 C3A C4 2.6(7) O2 C3 C3A C4 -177.8(4) C7A C3A C4 C5 -13.9(7) C3 C3A C4 C5 164.7(5) C3A C4 C5 C6 41.4(8) C4 C5 C6 C7 -54.8(9) C3 C3A C7A C7 178.6(4) C4 C3A C7A C7 -2.6(6) C3 C3A C7A C1 -.6(4) C4 C3A C7A C1 178.2(4) O2 C1 C7A C3A .0(4) C8 C1 C7A C3A -121.3(4) O2 C1 C7A C7 -179.2(3) C8 C1 C7A C7 59.5(5) C3A C7A C7 C6 -6.5(6) C1 C7A C7 C6 172.6(4) C5 C6 C7 C7A 34.1(7) O2 C1 C8 C9 32.7(4) C7A C1 C8 C9 150.1(3) O2 C1 C8 C13 160.2(3) C7A C1 C8 C13 -82.4(4) C13 C8 C9 C14 -72.6(4) C1 C8 C9 C14 54.2(4) C13 C8 C9 C10 51.9(4) C1 C8 C9 C10 178.7(3) C14 C9 C10 C11 71.6(5) C8 C9 C10 C11 -55.9(4) C9 C10 C11 C12 58.5(5) C10 C11 C12 C13 -57.2(6) C11 C12 C13 C8 53.9(5) C9 C8 C13 C12 -51.4(5) C1 C8 C13 C12 -179.8(3) C8 C9 C14 O3 6.3(5) C10 C9 C14 O3 -118.8(4) C8 C9 C14 O4 -173.9(3) C10 C9 C14 O4 61.1(4)