#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/07/2010709.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_2010709 loop_ _publ_author_name 'Wong, Jesse K.' 'Macalintal, Rose Ann R.' 'Brunskill, Andrew P. J.' 'Lalancette, Roger A.' 'Thompson, Hugh W.' _publ_section_title ; 7-Oxobicyclo[2.2.1]heptane-1-carboxylic acid and (+-)-7-oxobicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid: hydrogen bonding in two norbornyl keto acids ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 371 _journal_page_last 373 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C8 H8 O3' _chemical_formula_sum 'C8 H8 O3' _chemical_formula_weight 152.14 _chemical_melting_point 376 _chemical_name_systematic ; (+-)-7-oxobicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 6.0039(9) _cell_length_b 10.5565(14) _cell_length_c 22.151(2) _cell_measurement_reflns_used 20 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 14.91 _cell_measurement_theta_min 11.36 _cell_volume 1403.9(3) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device '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 .032 _diffrn_reflns_av_sigmaI/netI .043 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_number 1719 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 25 _diffrn_reflns_theta_min 1.84 _diffrn_standards_decay_% 'variation < 1' _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .111 _exptl_absorpt_correction_type none _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Parallelepiped _exptl_crystal_F_000 640 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .35 _refine_diff_density_max .20 _refine_diff_density_min -.18 _refine_ls_extinction_coef .006(2) _refine_ls_extinction_method 'SHELXTL (Sheldrick, 1997)' _refine_ls_goodness_of_fit_ref 1.03 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 104 _refine_ls_number_reflns 1231 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.03 _refine_ls_R_factor_all .082 _refine_ls_R_factor_gt .048 _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^)+(0.0578P)^2^+0.5877P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .136 _reflns_number_gt 827 _reflns_number_total 1231 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fg1572.cif _[local]_cod_data_source_block II _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_geom_hbond_publ_flag' value 'Y' changed to 'y' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3 times). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2010709 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' '-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 1.0504(3) .0811(2) .33012(10) .0586(6) Uani d . 1 . . O O2 .4114(3) .3839(2) .45480(9) .0610(7) Uani d . 1 . . O O3 .7598(3) .4300(3) .47880(10) .0709(8) Uani d . 1 . . O C1 .9472(4) .2644(2) .39442(11) .0387(7) Uani d . 1 . . C C2 .6964(4) .2604(3) .41086(11) .0384(7) Uani d . 1 . . C C3 .5778(4) .2520(3) .34818(11) .0423(7) Uani d . 1 . . C C4 .7744(4) .2472(3) .30315(11) .0440(7) Uani d . 1 . . C C5 .8909(5) .3717(3) .30560(12) .0470(8) Uani d . 1 . . C C6 .9906(4) .3825(3) .35875(13) .0428(7) Uani d . 1 . . C C7 .9441(4) .1748(3) .34063(12) .0408(7) Uani d . 1 . . C C8 .6155(4) .3664(3) .44957(10) .0401(7) Uani d . 1 . . C H2 .3888 .4408 .4793 .091 Uiso calc PR .35(5) . . H H3 .6967 .4839 .4993 .106 Uiso calc PR .65(5) . . H H1A 1.0528 .2448 .4268 .046 Uiso calc R 1 . . H H2A .6682 .1810 .4324 .046 Uiso calc R 1 . . H H3A .4869 .1763 .3453 .051 Uiso calc R 1 . . H H3B .4849 .3257 .3411 .051 Uiso calc R 1 . . H H4A .7420 .2135 .2629 .053 Uiso calc R 1 . . H H5A .8933 .4319 .2749 .056 Uiso calc R 1 . . H H6A 1.0736 .4517 .3717 .051 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 .0510(12) .0465(12) .0784(15) .0101(11) .0038(11) -.0068(11) O2 .0412(12) .0892(18) .0526(13) .0042(11) .0018(10) -.0224(11) O3 .0457(12) .0923(18) .0747(15) -.0107(12) .0069(12) -.0401(14) C1 .0321(13) .0465(15) .0375(14) .0028(12) -.0069(11) .0010(12) C2 .0350(14) .0436(14) .0365(13) -.0026(13) .0007(11) .0042(12) C3 .0327(13) .0471(15) .0472(15) -.0001(13) -.0044(12) -.0067(13) C4 .0403(15) .0574(17) .0343(13) .0065(14) -.0036(12) -.0049(13) C5 .0461(17) .0504(17) .0447(15) .0098(14) .0095(14) .0102(13) C6 .0337(14) .0419(15) .0528(16) -.0009(12) .0053(13) -.0016(13) C7 .0336(14) .0385(14) .0504(15) .0022(13) .0037(12) .0012(13) C8 .0382(15) .0516(16) .0304(13) -.0047(13) .0000(12) .0000(12) 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 C7 . 1.200(3) ? O2 C8 . 1.245(3) y O3 C8 . 1.273(3) y C1 C6 . 1.498(4) ? C1 C7 . 1.522(4) ? C1 C2 . 1.550(3) ? C2 C8 . 1.491(4) ? C2 C3 . 1.563(3) ? C3 C4 . 1.546(3) ? C4 C5 . 1.490(4) ? C4 C7 . 1.520(4) ? C5 C6 . 1.326(4) ? 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 C6 C1 C7 96.1(2) ? C6 C1 C2 108.4(2) ? C7 C1 C2 98.9(2) ? C8 C2 C1 115.5(2) ? C8 C2 C3 113.9(2) ? C1 C2 C3 103.63(19) ? C4 C3 C2 103.12(19) ? C5 C4 C7 96.3(2) ? C5 C4 C3 107.8(2) ? C7 C4 C3 100.1(2) ? C6 C5 C4 108.7(2) ? C5 C6 C1 108.6(2) ? O1 C7 C4 131.7(3) ? O1 C7 C1 131.1(3) ? C4 C7 C1 97.1(2) ? O2 C8 O3 123.0(3) ? O2 C8 C2 119.1(2) y O3 C8 C2 117.8(2) y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _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 C1 H1A O2 1_555 1_555 1_655 .98 2.68 3.339(3) 125 y C3 H3B O1 1_555 1_555 8_765 .97 2.71 3.580(4) 149 y O3 H3 O2 1_555 1_555 5_666 .82 1.84 2.660(3) 173 y 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 C6 C1 C2 C8 -62.1(3) C7 C1 C2 C8 -161.7(2) C6 C1 C2 C3 63.2(3) C7 C1 C2 C3 -36.4(3) C8 C2 C3 C4 128.3(2) C1 C2 C3 C4 2.0(3) C2 C3 C4 C5 -66.8(3) C2 C3 C4 C7 33.2(3) C7 C4 C5 C6 -34.1(3) C3 C4 C5 C6 68.6(3) C4 C5 C6 C1 .5(3) C7 C1 C6 C5 33.3(3) C2 C1 C6 C5 -68.3(3) C5 C4 C7 O1 -123.7(3) C3 C4 C7 O1 126.9(3) C5 C4 C7 C1 52.8(2) C3 C4 C7 C1 -56.6(2) C6 C1 C7 O1 124.2(3) C2 C1 C7 O1 -126.1(3) C6 C1 C7 C4 -52.3(2) C2 C1 C7 C4 57.4(2) C1 C2 C8 O2 165.9(2) C3 C2 C8 O2 46.1(3) C1 C2 C8 O3 -18.4(4) C3 C2 C8 O3 -138.2(3) _cod_database_fobs_code 2010709 _journal_paper_doi 10.1107/S0108270199015747