#------------------------------------------------------------------------------ #$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/48/2204823.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_2204823 loop_ _publ_author_name '\,Samil I\,s\?ik' 'Yavuz K\"oysal' 'Metin Yavuz' 'Mer\,c K\"oksal' 'Hakk\?i Erdo\~gan' _publ_section_title ; 5-(2-Chlorobenzoyl)-1,3-benzoxazol-2(3H)-one ; _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o2321 _journal_page_last o2323 _journal_paper_doi 10.1107/S1600536804029162 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H8 Cl N O3' _chemical_formula_moiety 'C14 H8 Cl N O3' _chemical_formula_sum 'C14 H8 Cl N O3' _chemical_formula_weight 273.66 _chemical_name_systematic ; 5-(2-Chlorobenzoyl)-1,3-benzoxazol-2(3H)-one ; _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.724(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.4550(9) _cell_length_b 7.8954(4) _cell_length_c 14.7960(12) _cell_measurement_reflns_used 16248 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 29.47 _cell_measurement_theta_min 0.00 _cell_volume 1218.78(16) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_data_reduction 'X-RED32 (Stoe & Cie, 2002)' _computing_molecular_graphics 'ORTEPIII (Burnett & Johnson, 1996)' _computing_publication_material ; WinGX (Farrugia, 1999) and PARST (Nardelli, 1995) ; _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 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Stoe IPDS-2' _diffrn_measurement_method \w _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 0.0721 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 21273 _diffrn_reflns_theta_full 29.57 _diffrn_reflns_theta_max 29.57 _diffrn_reflns_theta_min 1.95 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.315 _exptl_absorpt_correction_T_max 0.9526 _exptl_absorpt_correction_T_min 0.8458 _exptl_absorpt_correction_type integration _exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)' _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.491 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.800 _exptl_crystal_size_mid 0.543 _exptl_crystal_size_min 0.230 _refine_diff_density_max 0.192 _refine_diff_density_min -0.270 _refine_ls_extinction_coef 0.016(3) _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 1.063 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 173 _refine_ls_number_reflns 3386 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.063 _refine_ls_R_factor_all 0.0570 _refine_ls_R_factor_gt 0.0417 _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^)+(0.065P)^2^+0.0757P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1170 _refine_ls_wR_factor_ref 0.1254 _reflns_number_gt 2456 _reflns_number_total 3386 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6306.cif _cod_data_source_block I _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2204823 _cod_database_fobs_code 2204823 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_type_symbol Cl1 0.54182(5) 0.42977(8) 0.60696(3) 0.0888(2) Uani d . 1 Cl N2 0.06810(12) 0.64851(15) 0.34687(8) 0.0544(3) Uani d . 1 N H2 0.0551 0.5712 0.3064 0.065 Uiso calc R 1 H C12 0.12115(12) 0.62144(16) 0.43396(8) 0.0437(3) Uani d . 1 C C7 0.26172(12) 0.35382(15) 0.62093(9) 0.0470(3) Uani d . 1 C C1 0.34078(12) 0.38164(15) 0.70827(9) 0.0471(3) Uani d . 1 C C13 0.16390(12) 0.48014(15) 0.48004(9) 0.0446(3) Uani d . 1 C H13 0.1592 0.3733 0.4536 0.053 Uiso calc R 1 H C11 0.12556(12) 0.77922(16) 0.47458(9) 0.0475(3) Uani d . 1 C C8 0.21478(11) 0.50389(15) 0.56853(8) 0.0432(3) Uani d . 1 C C9 0.21956(14) 0.66443(17) 0.60784(9) 0.0517(3) Uani d . 1 C H9 0.2548 0.6765 0.6668 0.062 Uiso calc R 1 H C2 0.46958(14) 0.42097(18) 0.70871(10) 0.0544(3) Uani d . 1 C O3 -0.00839(13) 0.88373(17) 0.26902(8) 0.0766(4) Uani d . 1 O C6 0.28643(14) 0.3683(2) 0.79058(10) 0.0606(4) Uani d . 1 C H6 0.2003 0.3396 0.7922 0.073 Uiso calc R 1 H C14 0.03996(14) 0.81317(19) 0.33499(10) 0.0561(3) Uani d . 1 C C10 0.17332(14) 0.80642(17) 0.56141(10) 0.0570(3) Uani d . 1 C H10 0.1747 0.9134 0.5877 0.068 Uiso calc R 1 H C3 0.54228(15) 0.4498(2) 0.78825(12) 0.0650(4) Uani d . 1 C H3 0.6286 0.4775 0.7871 0.078 Uiso calc R 1 H C5 0.35842(19) 0.3973(3) 0.87036(12) 0.0733(5) Uani d . 1 C H5 0.3205 0.3898 0.9254 0.088 Uiso calc R 1 H C4 0.48622(18) 0.4372(3) 0.86873(13) 0.0732(5) Uani d . 1 C H4 0.5347 0.4558 0.9228 0.088 Uiso calc R 1 H O2 0.07579(10) 0.89773(12) 0.41344(7) 0.0581(3) Uani d . 1 O O1 0.23532(12) 0.21141(13) 0.59548(8) 0.0700(3) Uani d . 1 O 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 Cl1 0.0718(3) 0.1268(5) 0.0693(3) -0.0127(3) 0.0159(2) 0.0144(3) N2 0.0677(7) 0.0517(6) 0.0421(6) -0.0008(5) -0.0091(5) 0.0004(5) C12 0.0464(6) 0.0435(6) 0.0403(6) -0.0037(5) -0.0029(5) -0.0009(5) C7 0.0539(6) 0.0394(6) 0.0470(7) -0.0015(5) -0.0022(5) -0.0006(5) C1 0.0534(7) 0.0403(6) 0.0468(7) 0.0010(5) -0.0036(5) 0.0038(5) C13 0.0497(6) 0.0387(5) 0.0447(6) -0.0014(5) -0.0011(5) -0.0041(5) C11 0.0523(6) 0.0388(6) 0.0501(7) -0.0009(5) -0.0062(5) 0.0037(5) C8 0.0465(6) 0.0388(5) 0.0437(6) -0.0018(5) -0.0021(5) -0.0009(5) C9 0.0662(8) 0.0416(6) 0.0455(7) -0.0013(5) -0.0101(6) -0.0050(5) C2 0.0573(7) 0.0510(7) 0.0542(8) -0.0015(6) -0.0019(6) 0.0069(6) O3 0.0908(8) 0.0741(8) 0.0618(7) -0.0014(6) -0.0196(6) 0.0229(6) C6 0.0577(8) 0.0725(9) 0.0510(8) -0.0013(7) 0.0005(6) 0.0017(7) C14 0.0615(7) 0.0541(7) 0.0514(8) -0.0036(6) -0.0062(6) 0.0090(6) C10 0.0750(9) 0.0381(6) 0.0556(8) 0.0008(6) -0.0127(7) -0.0075(5) C3 0.0575(8) 0.0662(9) 0.0689(10) -0.0051(7) -0.0139(7) 0.0054(8) C5 0.0819(11) 0.0908(12) 0.0464(8) 0.0016(9) -0.0008(7) 0.0008(8) C4 0.0780(10) 0.0820(11) 0.0564(9) 0.0000(8) -0.0195(8) -0.0034(8) O2 0.0701(6) 0.0424(5) 0.0595(6) -0.0003(4) -0.0132(5) 0.0077(4) O1 0.0994(8) 0.0385(5) 0.0683(7) -0.0024(5) -0.0230(6) -0.0004(4) 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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 C14 N2 C12 110.01(12) C14 N2 H2 125.0 C12 N2 H2 125.0 C13 C12 C11 121.18(12) C13 C12 N2 133.44(12) C11 C12 N2 105.38(11) O1 C7 C8 121.21(12) O1 C7 C1 120.25(12) C8 C7 C1 118.52(10) C6 C1 C2 118.01(13) C6 C1 C7 120.79(12) C2 C1 C7 121.20(13) C12 C13 C8 116.82(11) C12 C13 H13 121.6 C8 C13 H13 121.6 C10 C11 O2 127.58(12) C10 C11 C12 123.42(12) O2 C11 C12 109.00(11) C13 C8 C9 121.03(12) C13 C8 C7 118.50(11) C9 C8 C7 120.47(11) C10 C9 C8 121.80(12) C10 C9 H9 119.1 C8 C9 H9 119.1 C3 C2 C1 121.64(14) C3 C2 Cl1 119.29(12) C1 C2 Cl1 119.06(11) C5 C6 C1 120.67(15) C5 C6 H6 119.7 C1 C6 H6 119.7 O3 C14 N2 129.07(15) O3 C14 O2 122.53(14) N2 C14 O2 108.40(12) C11 C10 C9 115.72(12) C11 C10 H10 122.1 C9 C10 H10 122.1 C4 C3 C2 119.28(15) C4 C3 H3 120.4 C2 C3 H3 120.4 C4 C5 C6 120.05(17) C4 C5 H5 120.0 C6 C5 H5 120.0 C3 C4 C5 120.33(16) C3 C4 H4 119.8 C5 C4 H4 119.8 C14 O2 C11 107.20(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C2 1.7290(16) yes N2 C14 1.3420(19) yes N2 C12 1.3859(16) yes N2 H2 0.8600 ? C12 C13 1.3674(17) ? C12 C11 1.3826(17) yes C7 O1 1.2119(16) yes C7 C8 1.4820(17) ? C7 C1 1.5042(18) ? C1 C6 1.381(2) ? C1 C2 1.3815(19) ? C13 C8 1.3936(17) ? C13 H13 0.9300 ? C11 C10 1.3649(19) ? C11 O2 1.3797(15) yes C8 C9 1.3941(18) ? C9 C10 1.3854(19) ? C9 H9 0.9300 ? C2 C3 1.378(2) ? O3 C14 1.2061(17) yes C6 C5 1.377(2) ? C6 H6 0.9300 ? C14 O2 1.3699(18) yes C10 H10 0.9300 ? C3 C4 1.365(3) ? C3 H3 0.9300 ? C5 C4 1.375(3) ? C5 H5 0.9300 ? C4 H4 0.9300 ? 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 N2 H2 O3 2_545 0.86 1.90 2.7498(16) 170 C10 H10 O1 1_565 0.93 2.44 3.2948(17) 153 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 C14 N2 C12 C13 178.98(14) C14 N2 C12 C11 -0.75(16) O1 C7 C1 C6 -78.12(19) C8 C7 C1 C6 100.42(15) O1 C7 C1 C2 101.82(17) C8 C7 C1 C2 -79.65(16) C11 C12 C13 C8 -1.61(19) N2 C12 C13 C8 178.69(13) C13 C12 C11 C10 0.9(2) N2 C12 C11 C10 -179.34(13) C13 C12 C11 O2 -179.49(11) N2 C12 C11 O2 0.28(15) C12 C13 C8 C9 0.92(19) C12 C13 C8 C7 179.76(11) O1 C7 C8 C13 -14.0(2) C1 C7 C8 C13 167.52(12) O1 C7 C8 C9 164.89(14) C1 C7 C8 C9 -13.63(18) C13 C8 C9 C10 0.6(2) C7 C8 C9 C10 -178.26(13) C6 C1 C2 C3 -1.3(2) C7 C1 C2 C3 178.78(13) C6 C1 C2 Cl1 177.33(11) C7 C1 C2 Cl1 -2.61(17) C2 C1 C6 C5 1.4(2) C7 C1 C6 C5 -178.67(14) C12 N2 C14 O3 -179.01(15) C12 N2 C14 O2 0.95(16) O2 C11 C10 C9 -178.94(13) C12 C11 C10 C9 0.6(2) C8 C9 C10 C11 -1.3(2) C1 C2 C3 C4 0.8(2) Cl1 C2 C3 C4 -177.81(14) C1 C6 C5 C4 -1.0(3) C2 C3 C4 C5 -0.4(3) C6 C5 C4 C3 0.5(3) O3 C14 O2 C11 179.21(15) N2 C14 O2 C11 -0.75(15) C10 C11 O2 C14 179.88(14) C12 C11 O2 C14 0.28(15) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 9498239