#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/31/2013148.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_2013148 loop_ _publ_author_name 'Papadakis, Markos M.' 'Pavon, Jorge A.' 'Lalancette, Roger A.' 'Thompson, Hugh W.' _publ_section_title ; The epimeric 9-oxobicyclo[3.3.1]nonane-3-carboxylic acids: hydrogen-bonding patterns of the endo acid and the lactol of the exo acid ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o167 _journal_page_last o170 _journal_paper_doi 10.1107/S0108270103001495 _journal_volume 59 _journal_year 2003 _chemical_formula_moiety 'C10 H14 O3' _chemical_formula_sum 'C10 H14 O3' _chemical_formula_weight 182.21 _chemical_melting_point 404 _chemical_name_systematic ; 9-oxobicyclo[3.3.1]nonane-3\a-carboxylic 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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 71.470(10) _cell_angle_beta 73.44(2) _cell_angle_gamma 77.290(10) _cell_formula_units_Z 2 _cell_length_a 6.6170(10) _cell_length_b 7.3160(10) _cell_length_c 10.421(2) _cell_measurement_reflns_used 23 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 9.9 _cell_measurement_theta_min 3.3 _cell_volume 453.81(14) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics 'SHELXP97 in SHELXTL' _computing_publication_material 'SHELXL97 in SHELXTL' _computing_structure_refinement 'SHELXL97 in SHELXTL' _computing_structure_solution 'SHELXS97 in SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method 2\q/\q _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 0.020 _diffrn_reflns_av_sigmaI/netI 0.041 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 2040 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.12 _diffrn_standards_decay_% 'variation < 1.1' _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.940 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(SHELXTL; Sheldrick, 1997)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'pentagonal rod' _exptl_crystal_F_000 196 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.08 _refine_diff_density_max 0.13 _refine_diff_density_min -0.17 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 121 _refine_ls_number_reflns 1588 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all 0.067 _refine_ls_R_factor_gt 0.042 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.0479P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.095 _refine_ls_wR_factor_ref 0.108 _reflns_number_gt 1141 _reflns_number_total 1588 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1406.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 453.81(13) _cod_database_code 2013148 _cod_database_fobs_code 2013148 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 0.8706(2) 0.8265(2) 0.46312(14) 0.0561(4) Uani d . 1 . . O O2 0.8195(2) 0.10089(19) 0.90893(15) 0.0554(4) Uani d . 1 . . O O3 1.0978(2) 0.2324(2) 0.90087(18) 0.0607(4) Uani d . 1 . . O C1 0.6182(3) 0.6068(3) 0.59638(19) 0.0400(5) Uani d . 1 . . C C2 0.6791(3) 0.4122(3) 0.7012(2) 0.0431(5) Uani d . 1 . . C C3 0.8636(3) 0.4217(3) 0.75880(19) 0.0394(5) Uani d . 1 . . C C4 0.8174(3) 0.5993(3) 0.81780(19) 0.0415(5) Uani d . 1 . . C C5 0.7591(3) 0.7915(3) 0.70982(19) 0.0391(5) Uani d . 1 . . C C6 0.5307(3) 0.8922(3) 0.7583(2) 0.0457(5) Uani d . 1 . . C C7 0.3613(3) 0.7696(3) 0.7749(2) 0.0470(5) Uani d . 1 . . C C8 0.3889(3) 0.7034(3) 0.6455(2) 0.0455(5) Uani d . 1 . . C C9 0.7651(3) 0.7493(3) 0.57578(19) 0.0386(4) Uani d . 1 . . C C10 0.9228(3) 0.2367(3) 0.8624(2) 0.0423(5) Uani d . 1 . . C H3 1.125(4) 0.115(4) 0.967(3) 0.080 Uiso d . 1 . . H H1 0.6318 0.5824 0.5069 0.048 Uiso calc R 1 . . H H2A 0.5564 0.3817 0.7775 0.052 Uiso calc R 1 . . H H2B 0.7192 0.3086 0.6555 0.052 Uiso calc R 1 . . H H3A 0.9878 0.4411 0.6801 0.047 Uiso calc R 1 . . H H4A 0.9421 0.6081 0.8457 0.050 Uiso calc R 1 . . H H4B 0.7008 0.5811 0.8998 0.050 Uiso calc R 1 . . H H5 0.8614 0.8804 0.6918 0.047 Uiso calc R 1 . . H H6A 0.5175 0.9171 0.8465 0.055 Uiso calc R 1 . . H H6B 0.5064 1.0166 0.6909 0.055 Uiso calc R 1 . . H H7A 0.3689 0.6561 0.8539 0.056 Uiso calc R 1 . . H H7B 0.2215 0.8452 0.7940 0.056 Uiso calc R 1 . . H H8A 0.3530 0.8150 0.5712 0.055 Uiso calc R 1 . . H H8B 0.2910 0.6115 0.6655 0.055 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 0.0579(9) 0.0587(9) 0.0442(8) -0.0183(7) 0.0080(7) -0.0145(7) O2 0.0549(9) 0.0459(8) 0.0662(10) -0.0143(7) -0.0196(8) -0.0065(7) O3 0.0521(10) 0.0502(9) 0.0822(11) -0.0088(7) -0.0307(8) -0.0071(8) C1 0.0418(11) 0.0447(10) 0.0387(10) -0.0071(8) -0.0074(8) -0.0196(8) C2 0.0428(11) 0.0381(10) 0.0538(11) -0.0075(9) -0.0108(9) -0.0191(9) C3 0.0359(11) 0.0382(10) 0.0449(11) -0.0056(8) -0.0044(8) -0.0165(9) C4 0.0405(11) 0.0449(11) 0.0440(11) -0.0071(9) -0.0081(9) -0.0198(9) C5 0.0402(11) 0.0374(10) 0.0435(10) -0.0114(8) -0.0049(8) -0.0166(8) C6 0.0502(12) 0.0418(11) 0.0477(11) -0.0028(9) -0.0072(9) -0.0220(9) C7 0.0374(11) 0.0503(12) 0.0532(12) -0.0019(9) -0.0035(9) -0.0232(10) C8 0.0414(11) 0.0457(11) 0.0526(12) -0.0077(9) -0.0112(9) -0.0163(9) C9 0.0358(10) 0.0360(10) 0.0406(11) -0.0031(8) -0.0028(9) -0.0126(8) C10 0.0362(11) 0.0427(11) 0.0497(11) -0.0016(9) -0.0066(9) -0.0206(9) 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 C9 C1 C8 107.26(14) ? C9 C1 C2 110.15(15) ? C8 C1 C2 112.69(16) ? C3 C2 C1 111.72(15) ? C10 C3 C2 112.79(15) ? C10 C3 C4 111.75(15) ? C2 C3 C4 111.18(15) ? C3 C4 C5 111.82(15) ? C9 C5 C6 106.21(15) ? C9 C5 C4 109.70(14) ? C6 C5 C4 112.40(15) ? C7 C6 C5 112.37(14) ? C8 C7 C6 112.17(16) ? C7 C8 C1 112.31(16) ? O1 C9 C1 123.43(17) ? O1 C9 C5 124.00(17) ? C1 C9 C5 112.52(15) ? O2 C10 O3 122.38(19) ? O2 C10 C3 123.67(18) y O3 C10 C3 113.94(17) y C10 O3 H3 110.4(16) ? C9 C1 H1 108.9 ? C8 C1 H1 108.9 ? C2 C1 H1 108.9 ? C3 C2 H2A 109.3 ? C1 C2 H2A 109.3 ? C3 C2 H2B 109.3 ? C1 C2 H2B 109.3 ? H2A C2 H2B 107.9 ? C10 C3 H3A 106.9 ? C2 C3 H3A 106.9 ? C4 C3 H3A 106.9 ? C3 C4 H4A 109.3 ? C5 C4 H4A 109.3 ? C3 C4 H4B 109.3 ? C5 C4 H4B 109.3 ? H4A C4 H4B 107.9 ? C9 C5 H5 109.5 ? C6 C5 H5 109.5 ? C4 C5 H5 109.5 ? C7 C6 H6A 109.1 ? C5 C6 H6A 109.1 ? C7 C6 H6B 109.1 ? C5 C6 H6B 109.1 ? H6A C6 H6B 107.9 ? C8 C7 H7A 109.2 ? C6 C7 H7A 109.2 ? C8 C7 H7B 109.2 ? C6 C7 H7B 109.2 ? H7A C7 H7B 107.9 ? C7 C8 H8A 109.1 ? C1 C8 H8A 109.1 ? C7 C8 H8B 109.1 ? C1 C8 H8B 109.1 ? H8A C8 H8B 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 C9 . 1.212(2) ? O2 C10 . 1.222(2) y O3 C10 . 1.320(2) y C1 C9 . 1.504(2) ? C1 C8 . 1.542(3) ? C1 C2 . 1.547(3) ? C2 C3 . 1.528(3) ? C3 C10 . 1.493(3) ? C3 C4 . 1.545(2) ? C4 C5 . 1.548(3) ? C5 C9 . 1.511(2) ? C5 C6 . 1.547(3) ? C6 C7 . 1.524(3) ? C7 C8 . 1.523(3) ? O3 H3 . 0.93(3) ? C1 H1 . 0.9800 ? C2 H2A . 0.9700 ? C2 H2B . 0.9700 ? C3 H3A . 0.9800 ? C4 H4A . 0.9700 ? C4 H4B . 0.9700 ? C5 H5 . 0.9800 ? C6 H6A . 0.9700 ? C6 H6B . 0.9700 ? C7 H7A . 0.9700 ? C7 H7B . 0.9700 ? C8 H8A . 0.9700 ? C8 H8B . 0.9700 ? 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 C9 C1 C2 C3 2.4(2) C8 C1 C2 C3 -117.33(16) C1 C2 C3 C10 178.88(14) C1 C2 C3 C4 52.4(2) C10 C3 C4 C5 179.21(15) C2 C3 C4 C5 -53.8(2) C3 C4 C5 C9 -0.2(2) C3 C4 C5 C6 117.70(17) C9 C5 C6 C7 56.4(2) C4 C5 C6 C7 -63.6(2) C5 C6 C7 C8 -51.8(2) C6 C7 C8 C1 50.9(2) C9 C1 C8 C7 -55.2(2) C2 C1 C8 C7 66.2(2) C8 C1 C9 O1 -113.6(2) C2 C1 C9 O1 123.4(2) C8 C1 C9 C5 63.92(19) C2 C1 C9 C5 -59.06(19) C6 C5 C9 O1 113.3(2) C4 C5 C9 O1 -125.0(2) C6 C5 C9 C1 -64.21(19) C4 C5 C9 C1 57.5(2) C2 C3 C10 O2 -8.3(2) C4 C3 C10 O2 117.8(2) C2 C3 C10 O3 172.09(15) C4 C3 C10 O3 -61.8(2)