#------------------------------------------------------------------------------ #$Date: 2016-02-19 22:18:51 +0000 (Fri, 19 Feb 2016) $ #$Revision: 176760 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/13/2011312.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_2011312 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 445.0(10) _chemical_name_systematic ; (+-)-cis-2-(3-Oxo-1,3,4,5,6,7-hexahydroisobenzofuran-1-yl)- cyclohexanecarboxylic acid ; _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-97 _cell_angle_alpha 66.180(10) _cell_angle_beta 88.200(10) _cell_angle_gamma 85.61(2) _cell_formula_units_Z 2 _cell_length_a 6.652(2) _cell_length_b 10.616(4) _cell_length_c 11.038(4) _cell_measurement_reflns_used 33 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13.34 _cell_measurement_theta_min 3.78 _cell_volume 711.0(4) _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 .970 _diffrn_measured_fraction_theta_max .970 _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 .034 _diffrn_reflns_av_sigmaI/netI .045 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4844 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.02 _diffrn_standards_decay_% 'variation < 1' _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .089 _exptl_absorpt_correction_T_max .99 _exptl_absorpt_correction_T_min .98 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'XPREP (Sheldrick, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'rectangular prism' _exptl_crystal_F_000 284 _exptl_crystal_size_max .60 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .16 _refine_diff_density_max .14 _refine_diff_density_min -.12 _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2422 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.01 _refine_ls_R_factor_all .059 _refine_ls_R_factor_gt .038 _refine_ls_shift/su_max .01 _refine_ls_shift/su_mean .00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0272P)^2^+0.1159P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .088 _reflns_number_gt 1790 _reflns_number_total 2422 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1276.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '444-446' was changed to '445.0(10)' - 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 '444-446' was changed to '445.0(10)' - the average value was taken and precision was estimated. '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 2011312 _cod_database_fobs_code 2011312 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_assembly _atom_site_disorder_group _atom_site_type_symbol O1 .80540(18) .56041(14) .60286(13) .0579(4) Uani d . 1 . . O O2 .48334(16) .64264(11) .60146(11) .0407(3) Uani d . 1 . . O O3 .4272(2) .91003(14) .65943(12) .0586(4) Uani d . 1 . . O O4 .2717(2) .93710(13) .47315(12) .0570(4) Uani d . 1 . . O C1 .2882(2) .58538(16) .64482(15) .0359(4) Uani d . 1 . . C C3 .6301(3) .53716(18) .62922(16) .0395(4) Uani d . 1 . . C C3A .5355(2) .40492(17) .69056(15) .0362(4) Uani d . 1 A . C C4 .6387(3) .26234(17) .73623(17) .0463(4) Uani d . 1 . . C C5 .489(3) .1550(14) .7665(14) .061(3) Uani d P .351(11) A 1 C C6 .3114(15) .1823(7) .8462(14) .067(3) Uani d P .351(11) A 1 C C5' .4905(13) .1563(8) .8223(7) .0594(15) Uani d P .649(11) A 2 C C6' .2806(6) .1866(4) .7606(8) .0654(15) Uani d P .649(11) A 2 C C7 .1887(3) .32496(18) .7541(2) .0552(5) Uani d . 1 . . C C7A .3382(2) .43209(16) .69956(15) .0367(4) Uani d . 1 A . C C8 .1894(2) .64056(16) .74287(15) .0355(4) Uani d . 1 . . C C9 .1195(2) .79612(16) .67575(16) .0390(4) Uani d . 1 . . C C10 .0184(3) .84559(19) .77873(18) .0512(5) Uani d . 1 . . C C11 .1440(3) .80718(18) .90404(17) .0512(5) Uani d . 1 . . C C12 .2033(3) .65251(18) .96661(17) .0504(5) Uani d . 1 . . C C13 .3154(3) .60468(17) .86779(16) .0430(4) Uani d . 1 . . C C14 .2863(3) .88605(16) .60161(16) .0410(4) Uani d . 1 . . C H1 .2002 .6121 .5676 .043 Uiso calc R 1 . . H H3 .5059 .9579 .6045 .088 Uiso calc PR .31(3) . . H H4 .3690 .9821 .4401 .086 Uiso calc PR .69(3) . . H H4A .7303 .2578 .6678 .056 Uiso calc PR .351(11) A 1 H H4B .7174 .2436 .8149 .056 Uiso calc PR .351(11) A 1 H H4A' .7579 .2565 .7864 .056 Uiso d PR .649(11) A 2 H H4B' .6798 .2431 .6609 .056 Uiso d PR .649(11) A 2 H H5A .5550 .0646 .8167 .073 Uiso calc PR .351(11) A 1 H H5B .4404 .1556 .6845 .073 Uiso calc PR .351(11) A 1 H H6A .3601 .1893 .9251 .080 Uiso calc PR .351(11) A 1 H H6B .2235 .1068 .8735 .080 Uiso calc PR .351(11) A 1 H H5'A .5421 .0645 .8330 .071 Uiso calc PR .649(11) A 2 H H5'B .4813 .1582 .9094 .071 Uiso calc PR .649(11) A 2 H H6'A .2897 .1883 .6720 .078 Uiso calc PR .649(11) A 2 H H6'B .1948 .1140 .8131 .078 Uiso calc PR .649(11) A 2 H H7A .1217 .3138 .6826 .066 Uiso calc PR .351(11) A 1 H H7B .0875 .3519 .8059 .066 Uiso calc PR .351(11) A 1 H H7A' .0696 .3526 .7001 .066 Uiso d PR .649(11) A 2 H H7B' .1503 .3157 .8419 .066 Uiso d PR .649(11) A 2 H H8 .0659 .5920 .7731 .043 Uiso calc R 1 . . H H9 .0161 .8058 .6107 .047 Uiso calc R 1 . . H H10A -.0067 .9451 .7377 .061 Uiso calc R 1 . . H H10B -.1109 .8059 .8036 .061 Uiso calc R 1 . . H H11A .2647 .8578 .8820 .061 Uiso calc R 1 . . H H11B .0667 .8334 .9673 .061 Uiso calc R 1 . . H H12A .0831 .6023 .9972 .061 Uiso calc R 1 . . H H12B .2889 .6319 1.0428 .061 Uiso calc R 1 . . H H13A .3460 .5056 .9092 .052 Uiso calc R 1 . . H H13B .4418 .6485 .8435 .052 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 .0404(8) .0617(9) .0710(9) -.0131(6) .0074(6) -.0250(7) O2 .0421(6) .0362(6) .0420(6) -.0092(5) .0084(5) -.0133(5) O3 .0761(9) .0606(9) .0415(7) -.0308(7) .0040(7) -.0188(6) O4 .0671(9) .0560(8) .0349(7) -.0091(7) -.0014(6) -.0038(6) C1 .0362(9) .0386(9) .0336(8) -.0070(7) .0013(7) -.0148(7) C3 .0400(10) .0465(10) .0358(9) -.0072(8) .0022(7) -.0201(8) C3A .0412(10) .0385(9) .0330(8) -.0056(7) .0018(7) -.0183(7) C4 .0509(11) .0455(11) .0441(10) .0008(9) .0005(8) -.0203(9) C5 .080(6) .037(4) .069(8) -.005(3) .014(7) -.027(6) C6 .076(6) .040(4) .086(7) -.022(3) .033(5) -.025(4) C5' .072(3) .036(2) .065(4) -.0037(18) .000(4) -.015(3) C6' .067(3) .0391(19) .093(4) -.0160(16) .004(2) -.027(2) C7 .0501(11) .0438(11) .0762(14) -.0140(9) .0143(10) -.0281(10) C7A .0423(10) .0372(9) .0361(9) -.0091(7) .0037(7) -.0194(7) C8 .0384(9) .0326(9) .0348(9) -.0079(7) .0038(7) -.0122(7) C9 .0413(9) .0373(9) .0364(9) -.0009(7) -.0039(7) -.0128(7) C10 .0579(12) .0431(10) .0506(11) .0040(9) .0055(9) -.0185(9) C11 .0699(13) .0437(11) .0428(10) -.0041(9) .0098(9) -.0209(9) C12 .0709(13) .0450(11) .0347(9) -.0040(9) .0028(9) -.0154(8) C13 .0549(11) .0362(9) .0361(9) .0010(8) -.0024(8) -.0132(7) C14 .0569(11) .0282(9) .0351(9) -.0008(8) -.0020(8) -.0100(7) 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 109.39(12) ? O2 C1 C7A 103.45(12) ? O2 C1 C8 110.41(12) ? C7A C1 C8 115.43(13) ? O1 C3 O2 121.03(16) ? O1 C3 C3A 130.20(17) ? O2 C3 C3A 108.77(14) ? C7A C3A C3 108.09(15) ? C7A C3A C4 124.73(15) ? C3 C3A C4 127.18(15) ? C5 C4 C3A 111.4(6) ? C5 C4 C5' 23.5(4) ? C3A C4 C5' 109.0(3) ? C4 C5 C6 110.8(10) ? C5 C6 C7 108.6(10) ? C6' C5' C4 111.8(5) ? C7 C6' C5' 110.3(5) ? C7A C7 C6' 110.2(2) ? C7A C7 C6 107.2(3) ? C6' C7 C6 35.3(3) ? C3A C7A C7 124.51(16) ? C3A C7A C1 110.29(14) ? C7 C7A C1 125.19(15) ? C13 C8 C1 113.43(13) ? C13 C8 C9 112.93(13) ? C1 C8 C9 112.55(13) ? C14 C9 C10 111.48(14) ? C14 C9 C8 113.31(14) ? C10 C9 C8 110.30(14) ? C11 C10 C9 113.83(15) ? C12 C11 C10 111.12(15) ? C11 C12 C13 111.34(15) ? C12 C13 C8 111.30(14) ? O3 C14 O4 122.43(16) ? O3 C14 C9 122.41(15) y O4 C14 C9 115.16(15) y C14 O3 H3 109.5 ? C14 O4 H4 109.5 ? O2 C1 H1 109.1 ? C7A C1 H1 109.1 ? C8 C1 H1 109.1 ? C5 C4 H4A 109.3 ? C3A C4 H4A 109.3 ? C5' C4 H4A 129.1 ? C5 C4 H4B 109.3 ? C3A C4 H4B 109.3 ? C5' C4 H4B 89.2 ? H4A C4 H4B 108.0 ? C5 C4 H4A' 126.9 ? C3A C4 H4A' 110.0 ? C5' C4 H4A' 110.3 ? H4A C4 H4A' 86.2 ? H4B C4 H4A' 23.5 ? C5 C4 H4B' 87.7 ? C3A C4 H4B' 109.8 ? C5' C4 H4B' 109.9 ? H4A C4 H4B' 24.1 ? H4B C4 H4B' 127.1 ? H4A' C4 H4B' 107.9 ? C4 C5 H5A 109.5 ? C6 C5 H5A 109.5 ? C4 C5 H5B 109.5 ? C6 C5 H5B 109.5 ? H5A C5 H5B 108.1 ? C5 C6 H6A 110.0 ? C7 C6 H6A 110.0 ? C5 C6 H6B 110.0 ? C7 C6 H6B 110.0 ? H6A C6 H6B 108.4 ? C6' C5' H5'A 109.3 ? C4 C5' H5'A 109.3 ? C6' C5' H5'B 109.3 ? C4 C5' H5'B 109.3 ? H5'A C5' H5'B 107.9 ? C7 C6' H6'A 109.6 ? C5' C6' H6'A 109.6 ? C7 C6' H6'B 109.6 ? C5' C6' H6'B 109.6 ? H6'A C6' H6'B 108.1 ? C7A C7 H7A 110.3 ? C6' C7 H7A 76.8 ? C6 C7 H7A 110.3 ? C7A C7 H7B 110.3 ? C6' C7 H7B 133.9 ? C6 C7 H7B 110.3 ? H7A C7 H7B 108.5 ? C7A C7 H7A' 110.1 ? C6' C7 H7A' 110.3 ? C6 C7 H7A' 137.4 ? H7A C7 H7A' 36.5 ? H7B C7 H7A' 75.0 ? C7A C7 H7B' 109.3 ? C6' C7 H7B' 109.1 ? C6 C7 H7B' 77.6 ? H7A C7 H7B' 134.7 ? H7B C7 H7B' 35.2 ? H7A' C7 H7B' 108.0 ? C13 C8 H8 105.7 ? C1 C8 H8 105.7 ? C9 C8 H8 105.7 ? C14 C9 H9 107.1 ? C10 C9 H9 107.1 ? C8 C9 H9 107.1 ? C11 C10 H10A 108.8 ? C9 C10 H10A 108.8 ? C11 C10 H10B 108.8 ? C9 C10 H10B 108.8 ? H10A C10 H10B 107.7 ? C12 C11 H11A 109.4 ? C10 C11 H11A 109.4 ? C12 C11 H11B 109.4 ? C10 C11 H11B 109.4 ? H11A C11 H11B 108.0 ? C11 C12 H12A 109.4 ? C13 C12 H12A 109.4 ? C11 C12 H12B 109.4 ? C13 C12 H12B 109.4 ? H12A C12 H12B 108.0 ? C12 C13 H13A 109.4 ? C8 C13 H13A 109.4 ? C12 C13 H13B 109.4 ? C8 C13 H13B 109.4 ? H13A C13 H13B 108.0 ? 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 . 1.212(2) ? O2 C3 . 1.369(2) ? O2 C1 . 1.4596(19) ? O3 C14 . 1.248(2) y O4 C14 . 1.301(2) y C1 C7A . 1.503(2) ? C1 C8 . 1.535(2) ? C3 C3A . 1.472(2) ? C3A C7A . 1.331(2) ? C3A C4 . 1.504(2) ? C4 C5 . 1.497(15) ? C4 C5' . 1.545(8) ? C5 C6 . 1.533(19) ? C6 C7 . 1.617(10) ? C5' C6' . 1.527(11) ? C6' C7 . 1.523(5) ? C7 C7A . 1.492(2) ? C8 C13 . 1.532(2) ? C8 C9 . 1.552(2) ? C9 C14 . 1.512(2) ? C9 C10 . 1.549(2) ? C10 C11 . 1.530(3) ? C11 C12 . 1.527(3) ? C12 C13 . 1.530(2) ? O3 H3 . .8200 ? O4 H4 . .8200 ? C1 H1 . .9800 ? C4 H4A . .9700 ? C4 H4B . .9700 ? C4 H4A' . .9650 ? C4 H4B' . .9605 ? C5 H5A . .9700 ? C5 H5B . .9700 ? C6 H6A . .9700 ? C6 H6B . .9700 ? C5' H5'A . .9700 ? C5' H5'B . .9700 ? C6' H6'A . .9700 ? C6' H6'B . .9700 ? C7 H7A . .9700 ? C7 H7B . .9700 ? C7 H7A' . .9601 ? C7 H7B' . .9626 ? C8 H8 . .9800 ? C9 H9 . .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 -1.03(15) C3 O2 C1 C8 123.03(14) C1 O2 C3 O1 -179.32(15) C1 O2 C3 C3A .96(16) O1 C3 C3A C7A 179.84(17) O2 C3 C3A C7A -.48(18) O1 C3 C3A C4 -.2(3) O2 C3 C3A C4 179.52(15) C7A C3A C4 C5 12.1(6) C3 C3A C4 C5 -167.9(6) C7A C3A C4 C5' -12.8(4) C3 C3A C4 C5' 167.2(3) C3A C4 C5 C6 -44.4(14) C5' C4 C5 C6 44.1(17) C4 C5 C6 C7 65.8(15) C5 C4 C5' C6' -56(2) C3A C4 C5' C6' 44.4(7) C4 C5' C6' C7 -64.0(9) C5' C6' C7 C7A 47.0(7) C5' C6' C7 C6 -44.6(6) C5 C6 C7 C7A -51.4(12) C5 C6 C7 C6' 49.3(9) C3 C3A C7A C7 178.75(16) C4 C3A C7A C7 -1.2(3) C3 C3A C7A C1 -.20(18) C4 C3A C7A C1 179.80(15) C6' C7 C7A C3A -16.1(4) C6 C7 C7A C3A 21.1(6) C6' C7 C7A C1 162.7(4) C6 C7 C7A C1 -160.1(5) O2 C1 C7A C3A .74(17) C8 C1 C7A C3A -119.97(15) O2 C1 C7A C7 -178.19(15) C8 C1 C7A C7 61.1(2) O2 C1 C8 C13 -59.94(17) C7A C1 C8 C13 56.91(18) O2 C1 C8 C9 69.83(17) C7A C1 C8 C9 -173.32(13) C13 C8 C9 C14 74.98(18) C1 C8 C9 C14 -55.04(18) C13 C8 C9 C10 -50.79(19) C1 C8 C9 C10 179.19(14) C14 C9 C10 C11 -76.23(19) C8 C9 C10 C11 50.6(2) C9 C10 C11 C12 -53.7(2) C10 C11 C12 C13 55.9(2) C11 C12 C13 C8 -56.7(2) C1 C8 C13 C12 -175.74(13) C9 C8 C13 C12 54.69(19) C10 C9 C14 O3 53.4(2) C8 C9 C14 O3 -71.7(2) C10 C9 C14 O4 -126.31(16) C8 C9 C14 O4 108.56(17)