#------------------------------------------------------------------------------ #$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204828.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_2204828 loop_ _publ_author_name 'Burcu Arslan' 'Canan Kazak' 'Hakan G\"oker' _publ_section_title ; 2,6-Dimethyl-4H-1-benzopyran-4-one ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2238 _journal_page_last o2240 _journal_paper_doi 10.1107/S1600536804027989 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C11 H10 O2' _chemical_formula_moiety 'C11 H10 O2' _chemical_formula_sum 'C11 H10 O2' _chemical_formula_weight 174.19 _chemical_name_systematic ; 2,6-Dimethyl-4H-1-benzopyran-4-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.979(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 5.4595(5) _cell_length_b 10.1947(14) _cell_length_c 15.8862(15) _cell_measurement_reflns_used 7949 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.4 _cell_measurement_theta_min 2.3 _cell_volume 882.06(17) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEP-3 (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 6.67 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Stoe IPDS-2' _diffrn_measurement_method 'rotation method' _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 0.088 _diffrn_reflns_av_sigmaI/netI 0.054 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 6705 _diffrn_reflns_theta_full 26.0 _diffrn_reflns_theta_max 26.0 _diffrn_reflns_theta_min 2.4 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.09 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.942 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 368 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.45 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.35 _refine_diff_density_min -0.24 _refine_ls_extinction_coef 0.093(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.11 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 135 _refine_ls_number_reflns 1740 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.11 _refine_ls_R_factor_all 0.066 _refine_ls_R_factor_gt 0.054 _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^)+(0.1083P)^2^+0.0774P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.175 _refine_ls_wR_factor_ref 0.184 _reflns_number_gt 1328 _reflns_number_total 1740 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ya6220.cif _cod_data_source_block III _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204828 _cod_database_fobs_code 2204828 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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_type_symbol O1 -0.2543(2) 0.52505(13) 0.10857(8) 0.0511(4) Uani d . 1 O O2 0.3617(3) 0.68843(16) 0.22357(9) 0.0697(5) Uani d . 1 O C1 -0.3200(4) 0.3829(2) 0.22073(15) 0.0607(6) Uani d D 1 C H1A -0.4548 0.3637 0.1806 0.091 Uiso calc RD 1 H H1B -0.3821 0.4130 0.2724 0.091 Uiso calc RD 1 H H1C -0.2240 0.3050 0.2315 0.091 Uiso calc RD 1 H C2 -0.1652(3) 0.48550(19) 0.18658(11) 0.0485(5) Uani d . 1 C C3 0.0386(3) 0.5368(2) 0.22472(12) 0.0511(5) Uani d . 1 C H3 0.085(4) 0.507(2) 0.2785(15) 0.068(6) Uiso d . 1 H C4 0.1773(3) 0.63785(19) 0.18847(11) 0.0485(5) Uani d . 1 C C4A 0.0809(3) 0.67825(17) 0.10306(10) 0.0444(5) Uani d . 1 C C5 0.1959(4) 0.77291(19) 0.05643(12) 0.0513(5) Uani d . 1 C H5 0.335(5) 0.811(2) 0.0815(15) 0.067(7) Uiso d . 1 H C6 0.1052(4) 0.80816(19) -0.02364(12) 0.0533(5) Uani d . 1 C C7 -0.1065(4) 0.7456(2) -0.05750(12) 0.0571(6) Uani d . 1 C H7 -0.171(5) 0.773(2) -0.1161(17) 0.076(7) Uiso d . 1 H C8 -0.2242(4) 0.6526(2) -0.01345(12) 0.0550(5) Uani d . 1 C H8 -0.373(4) 0.609(2) -0.0343(15) 0.064(6) Uiso d . 1 H C9 -0.1297(3) 0.61906(18) 0.06751(11) 0.0451(5) Uani d . 1 C C10 0.2281(5) 0.9122(2) -0.07349(15) 0.0726(7) Uani d D 1 C H10A 0.1391 0.9232 -0.1273 0.109 Uiso calc RD 1 H H10B 0.3936 0.8860 -0.0818 0.109 Uiso calc RD 1 H H10C 0.2299 0.9936 -0.0431 0.109 Uiso calc RD 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 0.0468(7) 0.0604(8) 0.0450(8) -0.0031(6) -0.0054(5) -0.0018(6) O2 0.0646(9) 0.0890(12) 0.0526(9) -0.0150(8) -0.0163(7) -0.0062(7) C1 0.0567(11) 0.0621(12) 0.0636(13) 0.0009(9) 0.0070(9) 0.0046(10) C2 0.0485(10) 0.0529(10) 0.0439(10) 0.0103(8) 0.0015(7) -0.0033(8) C3 0.0512(11) 0.0620(12) 0.0392(10) 0.0070(8) -0.0028(8) -0.0013(8) C4 0.0467(10) 0.0589(11) 0.0387(9) 0.0040(8) -0.0048(7) -0.0102(8) C4A 0.0463(10) 0.0497(10) 0.0367(9) 0.0053(7) 0.0000(7) -0.0100(7) C5 0.0519(11) 0.0553(11) 0.0464(10) -0.0002(9) 0.0018(8) -0.0098(8) C6 0.0599(12) 0.0558(11) 0.0448(10) 0.0089(9) 0.0096(8) -0.0035(8) C7 0.0611(12) 0.0680(13) 0.0414(10) 0.0121(10) -0.0016(8) -0.0012(9) C8 0.0508(11) 0.0694(13) 0.0434(10) 0.0011(9) -0.0084(8) -0.0045(9) C9 0.0434(9) 0.0520(10) 0.0393(9) 0.0049(7) -0.0012(7) -0.0071(7) C10 0.0918(17) 0.0669(14) 0.0604(13) 0.0009(12) 0.0145(12) 0.0069(10) 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 C2 O1 C9 118.97(14) C3 C2 O1 122.06(18) C3 C2 C1 126.33(18) O1 C2 C1 111.61(16) C2 C3 C4 123.32(18) C2 C3 H3 117.2(15) C4 C3 H3 119.4(15) O2 C4 C3 124.17(17) O2 C4 C4A 121.80(19) C3 C4 C4A 114.03(16) C9 C4A C5 118.53(17) C9 C4A C4 119.04(17) C5 C4A C4 122.42(17) O1 C9 C4A 122.53(16) O1 C9 C8 116.61(16) C4A C9 C8 120.86(18) C7 C8 C9 119.09(18) C7 C8 H8 124.2(14) C9 C8 H8 116.7(14) C8 C7 C6 121.79(18) C8 C7 H7 121.2(14) C6 C7 H7 117.0(14) C5 C6 C7 118.08(19) C5 C6 C10 121.5(2) C7 C6 C10 120.39(19) C6 C5 C4A 121.65(19) C6 C5 H5 121.4(15) C4A C5 H5 117.0(15) C2 C1 H1A 109.5 C2 C1 H1B 109.5 H1A C1 H1B 109.5 C2 C1 H1C 109.5 H1A C1 H1C 109.5 H1B C1 H1C 109.5 C6 C10 H10A 109.5 C6 C10 H10B 109.5 H10A C10 H10B 109.5 C6 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C2 1.361(2) O1 C9 1.367(2) O2 C4 1.230(2) C2 C3 1.336(3) C2 C1 1.472(3) C3 C4 1.424(3) C3 H3 0.93(2) C4 C4A 1.479(2) C4A C9 1.384(3) C4A C5 1.392(3) C9 C8 1.395(3) C8 C7 1.365(3) C8 H8 0.96(2) C7 C6 1.395(3) C7 H7 1.01(3) C6 C5 1.380(3) C6 C10 1.509(3) C5 H5 0.92(3) C1 H1A 0.9600 C1 H1B 0.9600 C1 H1C 0.9600 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 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 C2 C3 0.8(3) C9 O1 C2 C1 -179.22(14) O1 C2 C3 C4 1.2(3) C1 C2 C3 C4 -178.82(17) C2 C3 C4 O2 178.10(19) C2 C3 C4 C4A -2.1(3) O2 C4 C4A C9 -178.97(17) C3 C4 C4A C9 1.2(2) O2 C4 C4A C5 1.8(3) C3 C4 C4A C5 -178.03(16) C2 O1 C9 C4A -1.6(2) C2 O1 C9 C8 177.81(16) C5 C4A C9 O1 179.86(15) C4 C4A C9 O1 0.6(3) C5 C4A C9 C8 0.4(3) C4 C4A C9 C8 -178.86(16) O1 C9 C8 C7 -179.71(16) C4A C9 C8 C7 -0.2(3) C9 C8 C7 C6 -0.2(3) C8 C7 C6 C5 0.5(3) C8 C7 C6 C10 -178.89(18) C7 C6 C5 C4A -0.3(3) C10 C6 C5 C4A 179.07(17) C9 C4A C5 C6 -0.2(3) C4 C4A C5 C6 179.11(17)