#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011797.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_2011797 loop_ _publ_author_name 'Barcon, Alan' 'Brunskill, Andrew P. J.' 'Lalancette, Roger A.' 'Thompson, Hugh W.' 'Miller, Allan J.' _publ_section_title ; (+-)-1-Tetralone-3-carboxylic acid and (+-)-1-tetralone-2-acetic acid: hydrogen bonding in two \g-keto acids ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 325 _journal_page_last 328 _journal_paper_doi 10.1107/S0108270100020783 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C11 H10 O3' _chemical_formula_sum 'C11 H10 O3' _chemical_formula_weight 190.19 _chemical_melting_point 420 _chemical_name_common '(+-)-1-tetralone-3-carboxylic acid' _chemical_name_systematic ; (+-)-4-oxo-1,2,3,4-tetrahydronaphthalene-2-carboxylic 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 91.339(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.2645(7) _cell_length_b 5.4440(12) _cell_length_c 26.170(3) _cell_measurement_reflns_used 52 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.2 _cell_measurement_theta_min 4.5 _cell_volume 892.3(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 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .999 _diffrn_measured_fraction_theta_max .999 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method 2\q/\q _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 .036 _diffrn_reflns_av_sigmaI/netI .047 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2499 _diffrn_reflns_theta_full 25.01 _diffrn_reflns_theta_max 25.01 _diffrn_reflns_theta_min 3.11 _diffrn_standards_decay_% 'variation < 0.7' _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .103 _exptl_absorpt_correction_T_max .990 _exptl_absorpt_correction_T_min .952 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details '(XPREP; Sheldrick, 1997)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_description trapezoid _exptl_crystal_F_000 400 _exptl_crystal_size_max .56 _exptl_crystal_size_mid .52 _exptl_crystal_size_min .10 _refine_diff_density_max .16 _refine_diff_density_min -.12 _refine_ls_extinction_coef .007(2) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 1582 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.06 _refine_ls_R_factor_all .076 _refine_ls_R_factor_gt .045 _refine_ls_shift/su_max .02 _refine_ls_shift/su_mean .00 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0365P)^2^+0.2370P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .106 _reflns_number_gt 1118 _reflns_number_total 1582 _reflns_threshold_expression I>2\s(I) _cod_data_source_file fr1312.cif _cod_data_source_block I _cod_original_cell_volume 892.2(2) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2011797 _cod_database_fobs_code 2011797 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 .5737(3) .0132(3) .32935(6) .0593(5) Uani d . 1 . . O O2 .5317(2) .2851(3) .45790(6) .0520(5) Uani d . 1 . . O O3 .2324(3) .3497(3) .49923(6) .0578(5) Uani d . 1 . . O C1 .0254(3) .1111(4) .41247(8) .0395(5) Uani d . 1 . . C C2 .2319(3) .0229(4) .43933(8) .0381(5) Uani d . 1 . . C C3 .3735(3) -.1033(4) .40087(8) .0412(5) Uani d . 1 . . C C4 .4159(3) .0512(4) .35437(8) .0379(5) Uani d . 1 . . C C4A .2603(3) .2459(4) .34021(7) .0325(5) Uani d . 1 . . C C5 .2993(4) .3989(4) .29891(8) .0424(5) Uani d . 1 . . C C6 .1558(4) .5779(4) .28460(8) .0473(6) Uani d . 1 . . C C7 -.0296(4) .6070(4) .31142(8) .0479(6) Uani d . 1 . . C C8A .0723(3) .2750(4) .36776(7) .0319(5) Uani d . 1 . . C C8 -.0702(3) .4573(4) .35246(8) .0407(5) Uani d . 1 . . C C9 .3473(3) .2316(4) .46586(7) .0377(5) Uani d . 1 . . C H3 .313(5) .483(5) .5117(11) .086(10) Uiso d . 1 . . H H1A -.0563 -.0300 .4006 .059(7) Uiso calc R 1 . . H H1B -.0604 .2003 .4367 .042(6) Uiso calc R 1 . . H H2 .1936 -.0982 .4653 .045(6) Uiso calc R 1 . . H H3A .5087 -.1445 .4175 .049(6) Uiso calc R 1 . . H H3B .3061 -.2555 .3900 .046(6) Uiso calc R 1 . . H H5 .4241 .3795 .2808 .048(6) Uiso calc R 1 . . H H6 .1834 .6793 .2569 .062(7) Uiso calc R 1 . . H H7 -.1273 .7279 .3018 .057(7) Uiso calc R 1 . . H H8 -.1956 .4788 .3703 .049(6) 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 .0442(9) .0674(12) .0670(11) .0143(9) .0161(8) -.0044(9) O2 .0411(10) .0612(11) .0538(9) -.0011(8) .0044(7) -.0221(9) O3 .0502(10) .0656(12) .0580(11) .0011(10) .0104(8) -.0236(10) C1 .0335(11) .0454(13) .0399(11) -.0025(11) .0034(9) -.0002(10) C2 .0430(12) .0364(11) .0349(10) .0000(10) .0000(9) .0040(10) C3 .0431(12) .0330(11) .0469(13) .0062(11) -.0084(10) -.0056(10) C4 .0340(11) .0386(12) .0412(11) .0008(10) -.0002(10) -.0119(10) C4A .0340(11) .0338(11) .0296(10) .0012(9) -.0008(8) -.0056(9) C5 .0440(12) .0485(13) .0351(11) -.0028(12) .0060(10) -.0037(11) C6 .0642(15) .0447(13) .0328(11) .0019(13) -.0026(10) .0034(11) C7 .0589(15) .0423(13) .0420(13) .0133(12) -.0111(11) -.0024(11) C8A .0298(10) .0343(11) .0313(10) -.0014(9) -.0046(8) -.0056(9) C8 .0347(12) .0471(13) .0401(11) .0066(11) -.0028(9) -.0048(10) C9 .0413(12) .0425(12) .0291(10) .0124(11) -.0022(9) .0031(10) 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 C8A C1 C2 111.32(17) ? C9 C2 C3 111.39(18) ? C9 C2 C1 111.40(17) ? C3 C2 C1 109.67(17) ? C4 C3 C2 113.48(17) ? O1 C4 C4A 121.7(2) ? O1 C4 C3 120.0(2) ? C4A C4 C3 118.26(17) ? C5 C4A C8A 119.76(19) ? C5 C4A C4 119.75(18) ? C8A C4A C4 120.49(18) ? C6 C5 C4A 120.8(2) ? C5 C6 C7 119.7(2) ? C8 C8A C4A 118.29(19) ? C8 C8A C1 120.82(18) ? C8 C7 C6 120.1(2) ? C4A C8A C1 120.89(18) ? C7 C8 C8A 121.3(2) ? O2 C9 O3 122.4(2) ? O2 C9 C2 123.3(2) y O3 C9 C2 114.3(2) y C9 O3 H3 108.1(18) ? C8A C1 H1A 109.4 ? C2 C1 H1A 109.4 ? C8A C1 H1B 109.4 ? C2 C1 H1B 109.4 ? H1A C1 H1B 108.0 ? C9 C2 H2 108.1 ? C3 C2 H2 108.1 ? C1 C2 H2 108.1 ? C4 C3 H3A 108.9 ? C2 C3 H3A 108.9 ? C4 C3 H3B 108.9 ? C2 C3 H3B 108.9 ? H3A C3 H3B 107.7 ? C6 C5 H5 119.6 ? C4A C5 H5 119.6 ? C5 C6 H6 120.1 ? C7 C6 H6 120.1 ? C8 C7 H7 119.9 ? C6 C7 H7 119.9 ? C7 C8 H8 119.4 ? C8A C8 H8 119.4 ? 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 C4 . 1.216(2) ? O2 C9 . 1.214(3) y O3 C9 . 1.313(3) y C1 C8A . 1.505(3) ? C1 C2 . 1.535(3) ? C2 C9 . 1.507(3) ? C2 C3 . 1.521(3) ? C3 C4 . 1.508(3) ? C4 C4A . 1.481(3) ? C4A C5 . 1.391(3) ? C4A C8A . 1.404(3) ? C5 C6 . 1.372(3) ? C6 C7 . 1.380(3) ? C7 C8 . 1.377(3) ? C8A C8 . 1.388(3) ? O3 H3 . .94(3) ? C1 H1A . .9700 ? C1 H1B . .9700 ? C2 H2 . .9800 ? C3 H3A . .9700 ? C3 H3B . .9700 ? C5 H5 . .9300 ? C6 H6 . .9300 ? C7 H7 . .9300 ? C8 H8 . .9300 ? 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 C8A C1 C2 C9 68.3(2) C8A C1 C2 C3 -55.5(2) C9 C2 C3 C4 -70.5(2) C1 C2 C3 C4 53.3(2) C2 C3 C4 O1 156.4(2) C2 C3 C4 C4A -24.2(3) O1 C4 C4A C5 -3.4(3) C3 C4 C4A C5 177.15(18) O1 C4 C4A C8A 175.7(2) C3 C4 C4A C8A -3.7(3) C8A C4A C5 C6 -.2(3) C4 C4A C5 C6 178.98(18) C4A C5 C6 C7 .0(3) C5 C6 C7 C8 .2(3) C5 C4A C8A C8 .2(3) C4 C4A C8A C8 -178.92(18) C5 C4A C8A C1 179.69(18) C4 C4A C8A C1 .5(3) C2 C1 C8A C8 -150.94(19) C2 C1 C8A C4A 29.6(3) C6 C7 C8 C8A -.1(3) C4A C8A C8 C7 -.1(3) C1 C8A C8 C7 -179.56(19) C3 C2 C9 O2 -1.7(3) C1 C2 C9 O2 -124.5(2) C3 C2 C9 O3 179.34(18) C1 C2 C9 O3 56.5(2) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 193598