#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/21/64/2216431.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_2216431 loop_ _publ_author_name 'Yang, Shu-Ping' 'Han, Li-Jun' 'Wang, Da-Qi' 'Xia, Hai-Tao' _publ_section_title ; Redetermination of 7-hydroxy-4-methyl-2H-1-benzopyran-2-one ; _journal_coeditor_code EZ2107 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o4643 _journal_page_last o4643 _journal_volume 63 _journal_year 2007 _chemical_formula_iupac 'C10 H8 O3' _chemical_formula_moiety 'C10 H8 O3' _chemical_formula_sum 'C10 H8 O3' _chemical_formula_weight 176.16 _chemical_melting_point 463 _chemical_name_common 7-hydroxy-4-methylcoumarin _chemical_name_systematic ; 7-hydroxy-4-methyl-2H-1-Benzopyran-2-one ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _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 5.229(3) _cell_length_b 11.875(6) _cell_length_c 13.161(6) _cell_measurement_reflns_used 1640 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 25.22 _cell_measurement_theta_min 2.32 _cell_volume 817.2(7) _computing_cell_refinement 'SMART (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction 'SAINT (Siemens, 1996)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material 'SHELXTL (Sheldrick, 1997b)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens SMART 1000 CCD area detector' _diffrn_measurement_method '\f and \w scans' _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 0.0436 _diffrn_reflns_av_sigmaI/netI 0.0298 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 4236 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.31 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_T_max 0.9677 _exptl_absorpt_correction_T_min 0.9507 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_description columnar _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.31 _refine_diff_density_max 0.201 _refine_diff_density_min -0.231 _refine_ls_abs_structure_details 'Flack (1983), 565 Freidel pairs' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 869 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0496 _refine_ls_R_factor_gt 0.0375 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0516P)^2^+0.1639P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0868 _refine_ls_wR_factor_ref 0.0976 _reflns_number_gt 732 _reflns_number_total 869 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ez2107.cif _[local]_cod_data_source_block I _cod_original_cell_volume 817.3(7) _cod_database_code 2216431 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_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_type_symbol _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 O O1 -0.0817(4) 0.08023(15) 0.22571(13) 0.0425(5) Uani d . 1 O O2 -0.1981(4) 0.10501(18) 0.06697(14) 0.0529(6) Uani d . 1 O O3 0.1286(5) 0.02230(17) 0.57207(14) 0.0511(6) Uani d . 1 H H3 0.0029 -0.0188 0.5685 0.077 Uiso calc R 1 C C1 -0.0515(6) 0.1327(2) 0.1341(2) 0.0391(7) Uani d . 1 C C2 0.1438(6) 0.2161(2) 0.1257(2) 0.0416(7) Uani d . 1 H H2 0.1637 0.2535 0.0641 0.050 Uiso calc R 1 C C3 0.3006(6) 0.2430(2) 0.2032(2) 0.0365(7) Uani d . 1 C C4 0.2715(5) 0.1833(2) 0.2979(2) 0.0349(7) Uani d . 1 C C5 0.4233(6) 0.1998(2) 0.3841(2) 0.0399(7) Uani d . 1 H H5 0.5588 0.2504 0.3809 0.048 Uiso calc R 1 C C6 0.3779(6) 0.1437(2) 0.4730(2) 0.0420(7) Uani d . 1 H H6 0.4844 0.1551 0.5286 0.050 Uiso calc R 1 C C7 0.1727(6) 0.0696(2) 0.4804(2) 0.0378(7) Uani d . 1 C C8 0.0219(6) 0.0483(2) 0.3964(2) 0.0378(7) Uani d . 1 H H8 -0.1127 -0.0027 0.4000 0.045 Uiso calc R 1 C C9 0.0750(5) 0.1044(2) 0.30701(18) 0.0343(6) Uani d . 1 C C10 0.4971(6) 0.3342(2) 0.1934(2) 0.0484(8) Uani d . 1 H H10A 0.6610 0.3057 0.2137 0.073 Uiso calc R 1 H H10B 0.4508 0.3965 0.2361 0.073 Uiso calc R 1 H H10C 0.5053 0.3589 0.1240 0.073 Uiso calc R 1 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 0.0424(12) 0.0494(11) 0.0358(10) -0.0115(11) -0.0033(9) 0.0021(9) O2 0.0535(13) 0.0650(13) 0.0402(11) -0.0092(12) -0.0113(11) -0.0009(10) O3 0.0579(14) 0.0548(11) 0.0405(11) -0.0058(12) -0.0015(11) 0.0087(9) C1 0.0398(17) 0.0432(16) 0.0342(14) 0.0004(13) -0.0010(13) 0.0000(13) C2 0.0458(17) 0.0428(15) 0.0361(15) -0.0024(14) 0.0051(14) 0.0037(12) C3 0.0359(16) 0.0343(13) 0.0391(15) 0.0002(13) 0.0080(14) -0.0027(12) C4 0.0305(14) 0.0368(14) 0.0373(15) 0.0006(12) 0.0034(12) -0.0059(12) C5 0.0341(16) 0.0413(14) 0.0444(16) -0.0075(13) 0.0003(15) -0.0042(13) C6 0.0375(16) 0.0482(15) 0.0402(14) -0.0017(15) -0.0049(14) -0.0043(13) C7 0.0389(16) 0.0370(14) 0.0376(14) 0.0034(13) 0.0048(14) 0.0007(12) C8 0.0352(15) 0.0371(14) 0.0411(15) -0.0038(13) 0.0019(13) -0.0007(12) C9 0.0324(15) 0.0366(14) 0.0340(13) -0.0001(13) -0.0021(13) -0.0044(12) C10 0.0506(17) 0.0442(16) 0.0505(17) -0.0077(16) 0.0058(17) 0.0018(13) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.366(3) O1 C9 1.378(3) O2 C1 1.215(3) O3 C7 1.351(3) O3 H3 0.8200 C1 C2 1.427(4) C2 C3 1.346(4) C2 H2 0.9300 C3 C4 1.443(4) C3 C10 1.498(4) C4 C9 1.396(4) C4 C5 1.399(4) C5 C6 1.367(4) C5 H5 0.9300 C6 C7 1.391(4) C6 H6 0.9300 C7 C8 1.381(4) C8 C9 1.380(4) C8 H8 0.9300 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 C9 121.4(2) C7 O3 H3 109.5 O2 C1 O1 116.5(2) O2 C1 C2 125.6(3) O1 C1 C2 117.9(2) C3 C2 C1 122.8(2) C3 C2 H2 118.6 C1 C2 H2 118.6 C2 C3 C4 118.2(2) C2 C3 C10 121.6(2) C4 C3 C10 120.1(2) C9 C4 C5 116.3(2) C9 C4 C3 118.8(2) C5 C4 C3 124.9(2) C6 C5 C4 121.8(3) C6 C5 H5 119.1 C4 C5 H5 119.1 C5 C6 C7 120.2(3) C5 C6 H6 119.9 C7 C6 H6 119.9 O3 C7 C8 122.8(3) O3 C7 C6 117.2(2) C8 C7 C6 120.0(2) C9 C8 C7 118.6(3) C9 C8 H8 120.7 C7 C8 H8 120.7 O1 C9 C8 116.2(2) O1 C9 C4 120.7(2) C8 C9 C4 123.0(2) C3 C10 H10A 109.5 C3 C10 H10B 109.5 H10A C10 H10B 109.5 C3 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 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 O1 C1 O2 179.5(2) C9 O1 C1 C2 -1.7(4) O2 C1 C2 C3 180.0(3) O1 C1 C2 C3 1.3(4) C1 C2 C3 C4 1.1(4) C1 C2 C3 C10 -177.5(3) C2 C3 C4 C9 -3.1(4) C10 C3 C4 C9 175.5(2) C2 C3 C4 C5 178.4(3) C10 C3 C4 C5 -2.9(4) C9 C4 C5 C6 -1.4(4) C3 C4 C5 C6 177.1(3) C4 C5 C6 C7 -1.5(4) C5 C6 C7 O3 -175.9(3) C5 C6 C7 C8 3.2(4) O3 C7 C8 C9 177.1(3) C6 C7 C8 C9 -1.9(4) C1 O1 C9 C8 178.3(3) C1 O1 C9 C4 -0.4(4) C7 C8 C9 O1 -179.9(2) C7 C8 C9 C4 -1.2(4) C5 C4 C9 O1 -178.6(2) C3 C4 C9 O1 2.9(4) C5 C4 C9 C8 2.8(4) C3 C4 C9 C8 -175.8(3) 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 O3 H3 O2 2_455 0.82 1.89 2.712(3) 175.3 C2 H2 O2 4 0.93 2.51 3.410(4) 161.6 _cod_database_fobs_code 2216431 _journal_paper_doi 10.1107/S1600536807056085