#------------------------------------------------------------------------------ #$Date: 2017-10-13 01:48:21 +0100 (Fri, 13 Oct 2017) $ #$Revision: 201957 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/23/2012355.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_2012355 loop_ _publ_author_name 'Laphookhieo, Surat' 'Karalai, Chatchanok' 'Chantrapromma, Suchada' 'Fun, Hoong-Kun' 'Usman, Anwar' 'Rat-a-pa, Yanisa' 'Chantrapromma, Kan' _publ_section_title ; Atomic charges of cerbinal ; _journal_issue 11 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1352 _journal_page_last 1353 _journal_paper_doi 10.1107/S0108270101014317 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C11 H8 O4' _chemical_formula_moiety 'C11 H8 O4' _chemical_formula_sum 'C11 H8 O4' _chemical_formula_weight 204.17 _chemical_melting_point 450.0(10) _chemical_name_common Cerbinal _chemical_name_systematic ; Methyl 1-formyl-6-oxa-6H-indene-4-carboxylate ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.8622(2) _cell_length_b 10.82440(10) _cell_length_c 12.3446(3) _cell_measurement_reflns_used 3144 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.34 _cell_measurement_theta_min 2.50 _cell_volume 916.95(4) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PLATON (Spek, 1990)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 8.33 _diffrn_measured_fraction_theta_full .995 _diffrn_measured_fraction_theta_max .995 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0829 _diffrn_reflns_av_sigmaI/netI .0635 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 6418 _diffrn_reflns_theta_full 28.28 _diffrn_reflns_theta_max 28.28 _diffrn_reflns_theta_min 2.50 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu .114 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 424 _exptl_crystal_size_max .46 _exptl_crystal_size_mid .16 _exptl_crystal_size_min .14 _refine_diff_density_max .354 _refine_diff_density_min -.446 _refine_ls_extinction_coef .015(5) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 138 _refine_ls_number_reflns 1323 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.007 _refine_ls_R_factor_all .0782 _refine_ls_R_factor_gt .0561 _refine_ls_shift/su_max .036 _refine_ls_shift/su_mean .002 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0799P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1446 _reflns_number_gt 900 _reflns_number_total 1323 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ta1345.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '449-451 K' was changed to '450.0(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 '449-451 K' was changed to '450.0(10)' - 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_database_code 2012355 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' 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 .1363(5) .3189(2) .16333(19) .0618(7) Uani d . 1 . . O O2 .1100(5) .12325(19) .72795(17) .0553(7) Uani d . 1 . . O O3 .1279(4) .47706(16) .49857(15) .0410(6) Uani d . 1 . . O O4 .1314(4) .3151(2) .79461(16) .0433(6) Uani d . 1 . . O C1 .1279(5) .2860(3) .4065(2) .0287(6) Uani d . 1 . . C C2 .1313(6) .4101(3) .4055(2) .0366(7) Uani d . 1 . . C H2A .1361 .4513 .3394 .044 Uiso calc R 1 . . H C3 .1239(6) .4169(3) .5954(2) .0356(7) Uani d . 1 . . C H3A .1218 .4641 .6583 .043 Uiso calc R 1 . . H C4 .1229(5) .2919(2) .6052(2) .0276(6) Uani d . 1 . . C C5 .1243(5) .2191(2) .5093(2) .0275(6) Uani d . 1 . . C C6 .1225(5) .0940(3) .4859(2) .0360(7) Uani d . 1 . . C H6A .1193 .0301 .5362 .043 Uiso calc R 1 . . H C7 .1263(6) .0807(3) .3717(2) .0398(7) Uani d . 1 . . C H7A .1266 .0054 .3354 .048 Uiso calc R 1 . . H C8 .1296(5) .1955(3) .3213(2) .0337(7) Uani d . 1 . . C C9 .1345(6) .2176(3) .2059(3) .0445(8) Uani d . 1 . . C H9A .1365 .1489 .1606 .053 Uiso calc R 1 . . H C10 .1214(5) .2336(3) .7136(2) .0339(6) Uani d . 1 . . C C11 .1271(7) .2634(3) .9036(2) .0490(9) Uani d . 1 . . C H11A .1352 .3291 .9557 .074 Uiso calc R 1 . . H H11B .2355 .2084 .9130 .074 Uiso calc R 1 . . H H11C .0076 .2188 .9139 .074 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 .0816(18) .0745(16) .0293(12) .004(2) .0014(14) .0078(12) O2 .0955(19) .0390(12) .0316(12) -.0035(16) -.0027(17) .0100(10) O3 .0637(14) .0296(9) .0298(11) -.0017(12) -.0017(14) .0028(9) O4 .0647(13) .0451(11) .0201(10) -.0038(15) -.0014(12) .0009(9) C1 .0267(13) .0351(13) .0242(13) -.0013(18) -.0014(14) .0001(12) C2 .0476(16) .0380(15) .0242(14) .000(2) .0031(17) .0060(12) C3 .0500(16) .0321(14) .0246(14) -.004(2) -.0007(18) -.0012(12) C4 .0288(13) .0312(13) .0227(13) -.0011(16) -.0002(15) .0012(11) C5 .0235(12) .0333(13) .0256(13) .0040(17) .0010(15) .0000(13) C6 .0415(15) .0311(13) .0354(16) -.0019(17) -.0005(19) -.0024(13) C7 .0441(16) .0403(16) .0349(16) .0051(19) -.0014(19) -.0118(13) C8 .0327(14) .0436(16) .0248(13) -.0013(19) .0015(15) -.0036(12) C9 .0468(18) .0605(19) .0261(15) -.001(2) .0032(18) -.0062(16) C10 .0360(15) .0414(16) .0243(13) -.0023(18) -.0012(18) .0037(12) C11 .064(2) .063(2) .0195(14) -.004(2) -.0014(18) .0049(13) 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 C2 O3 C3 119.2(2) yes C10 O4 C11 115.9(2) yes C2 C1 C8 132.4(3) ? C2 C1 C5 120.3(3) ? C8 C1 C5 107.3(2) ? C1 C2 O3 121.6(2) ? C1 C2 H2A 119.2 ? O3 C2 H2A 119.2 ? C4 C3 O3 123.7(3) ? C4 C3 H3A 118.1 ? O3 C3 H3A 118.1 ? C3 C4 C5 118.5(2) ? C3 C4 C10 120.4(2) ? C5 C4 C10 121.1(2) ? C6 C5 C4 135.6(3) ? C6 C5 C1 107.7(3) ? C4 C5 C1 116.7(2) ? C5 C6 C7 107.8(3) ? C5 C6 H6A 126.1 ? C7 C6 H6A 126.1 ? C8 C7 C6 110.8(3) ? C8 C7 H7A 124.6 ? C6 C7 H7A 124.6 ? C7 C8 C1 106.3(2) ? C7 C8 C9 126.1(3) ? C1 C8 C9 127.6(3) ? O1 C9 C8 125.1(3) yes O1 C9 H9A 117.5 ? C8 C9 H9A 117.5 ? O2 C10 O4 123.1(3) ? O2 C10 C4 123.7(3) ? O4 C10 C4 113.2(2) ? O4 C11 H11A 109.5 ? O4 C11 H11B 109.5 ? H11A C11 H11B 109.5 ? O4 C11 H11C 109.5 ? H11A C11 H11C 109.5 ? H11B C11 H11C 109.5 ? 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 . 1.217(4) yes O2 C10 . 1.210(3) yes O3 C2 . 1.359(3) yes O3 C3 . 1.361(3) yes O4 C10 . 1.336(4) yes O4 C11 . 1.457(4) yes C1 C2 . 1.344(4) yes C1 C8 . 1.438(4) ? C1 C5 . 1.461(4) ? C2 H2A . .9300 ? C3 C4 . 1.359(4) yes C3 H3A . .9300 ? C4 C5 . 1.423(4) ? C4 C10 . 1.479(4) ? C5 C6 . 1.384(4) ? C6 C7 . 1.417(4) ? C6 H6A . .9300 ? C7 C8 . 1.390(4) ? C7 H7A . .9300 ? C8 C9 . 1.445(4) ? C9 H9A . .9300 ? C11 H11A . .9600 ? C11 H11B . .9600 ? C11 H11C . .9600 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _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 C11 H11A O1 1_556 .96 2.5658 3.262(3) 130 yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21135063