#------------------------------------------------------------------------------ #$Date: 2014-10-12 00:58:37 +0300 (Sun, 12 Oct 2014) $ #$Revision: 125282 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/00/2240070.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_2240070 loop_ _publ_author_name 'Shoaib, Mohammad' 'Shah, Ismail' 'Shah, Syed Wadood Ali' 'Tahir, Muhammad Nawaz' 'Ullah, Shafi' 'Ayaz, Muhammad' _publ_section_title ; Crystal structure of 3-[(2-acetylphenoxy)carbonyl]benzoic acid ; _journal_coeditor_code HB7293 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1153 _journal_paper_doi 10.1107/S1600536814021904 _journal_volume 70 _journal_year 2014 _chemical_formula_iupac 'C16 H12 O5' _chemical_formula_moiety 'C16 H12 O5' _chemical_formula_sum 'C16 H12 O5' _chemical_formula_weight 284.26 _chemical_name_systematic ; 3-[(2-Acetylphenoxy)carbonyl]benzoic acid ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90 _cell_angle_beta 106.671(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.5081(10) _cell_length_b 7.4743(6) _cell_length_c 13.9421(11) _cell_measurement_reflns_used 1971 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 26.0 _cell_measurement_theta_min 1.851 _cell_volume 1348.48(18) _computing_cell_refinement ; SAINT (Bruker, 2007) ; _computing_data_collection ; APEX2 (Bruker, 2007) ; _computing_data_reduction ; SAINT (Bruker, 2007) ; _computing_molecular_graphics ; ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009) ; _computing_publication_material ; WinGX (Farrugia, 2012) and PLATON (Spek, 2009) ; _computing_structure_refinement ; SHELXL97 (Sheldrick, 2008) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2008) ; _diffrn_ambient_temperature 296(2) _diffrn_detector_area_resol_mean 7.50 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker Kappa APEXII CCD' _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 0.0221 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 10280 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 26.000 _diffrn_reflns_theta_min 1.851 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (SADABS; Bruker, 2005) ; _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.180 _refine_diff_density_min -0.202 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2655 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0578 _refine_ls_R_factor_gt 0.0409 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.4011P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1024 _refine_ls_wR_factor_ref 0.1151 _reflns_number_gt 1971 _reflns_number_total 2655 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file hb7293sup1.cif _[local]_cod_data_source_block I _cod_database_code 2240070 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL I1LUOM_0m in P2(1)/n LIGHT YELLOW PRISM CELL 0.71073 13.5081 7.4743 13.9421 90.000 106.671 90.000 ZERR 4.00 0.0010 0.0006 0.0011 0.000 0.003 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H O UNIT 64 48 20 OMIT -3 52 L.S. 40 ACTA BOND $H HTAB CONF LIST 4 FMAP 2 PLAN 8 SIZE 0.38 0.28 0.25 TEMP 23.000 EQIV $1 -x+1, -y, -z+1 HTAB O1 O2_$1 WGHT 0.050500 0.401100 FVAR 0.17921 O1 3 0.361301 0.031134 0.473663 11.00000 0.04548 0.13791 = 0.02725 -0.00554 0.00970 0.00687 AFIX 147 H1 2 0.416628 0.027557 0.517650 11.00000 -1.50000 AFIX 0 O2 3 0.464739 -0.005786 0.376935 11.00000 0.03632 0.11885 = 0.03230 -0.00241 0.00887 0.00229 O3 3 0.146947 -0.006650 -0.058140 11.00000 0.03914 0.12448 = 0.03280 0.00151 0.00371 0.01392 O4 3 0.315643 -0.052737 0.016339 11.00000 0.03250 0.06526 = 0.02637 -0.00067 0.00966 -0.00047 O5 3 0.481903 0.296546 -0.115617 11.00000 0.09161 0.07482 = 0.07914 -0.00726 0.04946 -0.02902 C1 1 0.377534 0.015442 0.386938 11.00000 0.04014 0.06287 = 0.02862 -0.00119 0.01162 -0.00131 C2 1 0.284221 0.022086 0.299125 11.00000 0.03565 0.04535 = 0.03049 0.00080 0.01037 -0.00178 C3 1 0.186682 0.047806 0.310859 11.00000 0.04296 0.05942 = 0.03206 -0.00312 0.01694 -0.00235 AFIX 43 H3 2 0.179124 0.062841 0.374601 11.00000 -1.20000 AFIX 0 C4 1 0.100858 0.051179 0.228402 11.00000 0.03376 0.07630 = 0.04493 -0.00541 0.01708 0.00174 AFIX 43 H4 2 0.035497 0.067305 0.236590 11.00000 -1.20000 AFIX 0 C5 1 0.112113 0.030563 0.133586 11.00000 0.03294 0.07058 = 0.03600 -0.00269 0.00715 0.00093 AFIX 43 H5 2 0.054187 0.033635 0.078037 11.00000 -1.20000 AFIX 0 C6 1 0.209662 0.005206 0.120660 11.00000 0.03242 0.04828 = 0.03004 0.00078 0.00966 -0.00113 C7 1 0.295930 0.000528 0.203555 11.00000 0.03133 0.05004 = 0.03115 0.00111 0.01129 -0.00181 AFIX 43 H7 2 0.361253 -0.016885 0.195510 11.00000 -1.20000 AFIX 0 C8 1 0.217029 -0.018328 0.016842 11.00000 0.03172 0.05743 = 0.03112 0.00272 0.00741 0.00099 C9 1 0.334297 -0.090015 -0.076173 11.00000 0.03174 0.05675 = 0.02558 -0.00065 0.00770 0.00284 C10 1 0.305623 -0.256414 -0.118179 11.00000 0.04739 0.05572 = 0.04179 -0.00267 0.01178 -0.00695 AFIX 43 H10 2 0.269193 -0.334997 -0.089171 11.00000 -1.20000 AFIX 0 C11 1 0.331473 -0.305445 -0.203747 11.00000 0.05436 0.06166 = 0.04803 -0.01728 0.00821 -0.00247 AFIX 43 H11 2 0.313180 -0.417817 -0.231898 11.00000 -1.20000 AFIX 0 C12 1 0.384333 -0.187563 -0.247154 11.00000 0.04994 0.08036 = 0.03764 -0.01352 0.01608 0.00329 AFIX 43 H12 2 0.401240 -0.219868 -0.304932 11.00000 -1.20000 AFIX 0 C13 1 0.411937 -0.022504 -0.204933 11.00000 0.04107 0.06918 = 0.03621 0.00048 0.01716 0.00215 AFIX 43 H13 2 0.447351 0.055887 -0.235127 11.00000 -1.20000 AFIX 0 C14 1 0.388454 0.031761 -0.117701 11.00000 0.02959 0.05224 = 0.03066 0.00125 0.00866 0.00365 C15 1 0.423936 0.215263 -0.078832 11.00000 0.04040 0.05548 = 0.04189 0.00467 0.01350 -0.00058 C16 1 0.389938 0.300344 0.003340 11.00000 0.07143 0.05308 = 0.06824 -0.01333 0.03349 -0.00767 AFIX 137 H16A 2 0.417367 0.419472 0.014769 11.00000 -1.50000 H16B 2 0.414759 0.231137 0.063473 11.00000 -1.50000 H16C 2 0.315829 0.305123 -0.015393 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM I1LUOM_0m in P2(1)/n LIGHT YELLOW PRISM REM R1 = 0.0409 for 1971 Fo > 4sig(Fo) and 0.0578 for all 2655 data REM 192 parameters refined using 0 restraints END WGHT 0.0505 0.4011 REM Instructions for potential hydrogen bonds HTAB O1 O2_$1 REM Highest difference peak 0.180, deepest hole -0.202, 1-sigma level 0.037 Q1 1 0.4176 0.3196 -0.1536 11.00000 0.05 0.18 Q2 1 0.3360 -0.0022 -0.1168 11.00000 0.05 0.17 Q3 1 0.2128 -0.0167 0.0806 11.00000 0.05 0.15 Q4 1 0.4220 -0.0168 -0.1356 11.00000 0.05 0.14 Q5 1 0.2945 0.0540 0.2666 11.00000 0.05 0.14 Q6 1 0.3247 0.0128 0.3338 11.00000 0.05 0.13 Q7 1 0.1439 -0.1228 -0.0348 11.00000 0.05 0.13 Q8 1 0.3210 0.2420 0.0126 11.00000 0.05 0.13 ; _shelxl_version_number 2014/6 loop_ _space_group_symop_operation_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_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_occupancy O O1 0.36130(10) 0.0311(2) 0.47366(9) 0.0704(5) Uani d 1 H H1 0.4166 0.0276 0.5177 0.106 Uiso calc 1 O O2 0.46474(9) -0.0058(2) 0.37694(9) 0.0627(4) Uani d 1 O O3 0.14695(9) -0.0066(2) -0.05814(9) 0.0669(4) Uani d 1 O O4 0.31564(8) -0.05274(16) 0.01634(7) 0.0411(3) Uani d 1 O O5 0.48190(13) 0.2965(2) -0.11562(12) 0.0767(5) Uani d 1 C C1 0.37753(13) 0.0154(2) 0.38694(11) 0.0435(4) Uani d 1 C C2 0.28422(12) 0.0221(2) 0.29912(11) 0.0370(4) Uani d 1 C C3 0.18668(13) 0.0478(2) 0.31086(12) 0.0435(4) Uani d 1 H H3 0.1791 0.0628 0.3746 0.052 Uiso calc 1 C C4 0.10086(13) 0.0512(3) 0.22840(13) 0.0505(5) Uani d 1 H H4 0.0355 0.0673 0.2366 0.061 Uiso calc 1 C C5 0.11211(13) 0.0306(3) 0.13359(13) 0.0471(4) Uani d 1 H H5 0.0542 0.0336 0.0780 0.056 Uiso calc 1 C C6 0.20966(12) 0.0052(2) 0.12066(11) 0.0368(4) Uani d 1 C C7 0.29593(12) 0.0005(2) 0.20355(11) 0.0370(4) Uani d 1 H H7 0.3613 -0.0169 0.1955 0.044 Uiso calc 1 C C8 0.21703(12) -0.0183(2) 0.01684(12) 0.0404(4) Uani d 1 C C9 0.33430(12) -0.0900(2) -0.07617(11) 0.0381(4) Uani d 1 C C10 0.30562(14) -0.2564(3) -0.11818(13) 0.0485(4) Uani d 1 H H10 0.2692 -0.3350 -0.0892 0.058 Uiso calc 1 C C11 0.33147(15) -0.3054(3) -0.20375(13) 0.0560(5) Uani d 1 H H11 0.3132 -0.4178 -0.2319 0.067 Uiso calc 1 C C12 0.38433(14) -0.1876(3) -0.24715(13) 0.0552(5) Uani d 1 H H12 0.4012 -0.2199 -0.3049 0.066 Uiso calc 1 C C13 0.41194(13) -0.0225(3) -0.20493(12) 0.0476(5) Uani d 1 H H13 0.4474 0.0559 -0.2351 0.057 Uiso calc 1 C C14 0.38845(12) 0.0318(2) -0.11770(11) 0.0375(4) Uani d 1 C C15 0.42394(13) 0.2153(2) -0.07883(12) 0.0456(4) Uani d 1 C C16 0.38994(17) 0.3003(3) 0.00334(16) 0.0614(5) Uani d 1 H H16A 0.4174 0.4195 0.0148 0.092 Uiso calc 1 H H16B 0.4148 0.2311 0.0635 0.092 Uiso calc 1 H H16C 0.3158 0.3051 -0.0154 0.092 Uiso calc 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 0.0455(8) 0.1379(14) 0.0272(6) 0.0069(9) 0.0097(5) -0.0055(7) O2 0.0363(7) 0.1189(13) 0.0323(6) 0.0023(7) 0.0089(5) -0.0024(7) O3 0.0391(7) 0.1245(13) 0.0328(7) 0.0139(7) 0.0037(5) 0.0015(7) O4 0.0325(6) 0.0653(8) 0.0264(5) -0.0005(5) 0.0097(4) -0.0007(5) O5 0.0916(11) 0.0748(10) 0.0791(10) -0.0290(9) 0.0495(9) -0.0073(8) C1 0.0401(10) 0.0629(12) 0.0286(8) -0.0013(8) 0.0116(7) -0.0012(7) C2 0.0356(9) 0.0454(10) 0.0305(8) -0.0018(7) 0.0104(6) 0.0008(6) C3 0.0430(10) 0.0594(11) 0.0321(8) -0.0023(8) 0.0169(7) -0.0031(7) C4 0.0338(9) 0.0763(13) 0.0449(10) 0.0017(9) 0.0171(8) -0.0054(9) C5 0.0329(9) 0.0706(13) 0.0360(9) 0.0009(8) 0.0071(7) -0.0027(8) C6 0.0324(8) 0.0483(10) 0.0300(8) -0.0011(7) 0.0097(6) 0.0008(7) C7 0.0313(8) 0.0500(10) 0.0312(8) -0.0018(7) 0.0113(6) 0.0011(7) C8 0.0317(8) 0.0574(11) 0.0311(8) 0.0010(7) 0.0074(7) 0.0027(7) C9 0.0317(8) 0.0567(11) 0.0256(7) 0.0028(7) 0.0077(6) -0.0007(7) C10 0.0474(10) 0.0557(11) 0.0418(9) -0.0069(9) 0.0118(8) -0.0027(8) C11 0.0544(11) 0.0617(13) 0.0480(10) -0.0025(9) 0.0082(9) -0.0173(9) C12 0.0499(11) 0.0804(15) 0.0376(9) 0.0033(10) 0.0161(8) -0.0135(9) C13 0.0411(9) 0.0692(13) 0.0362(9) 0.0021(8) 0.0172(7) 0.0005(8) C14 0.0296(8) 0.0522(10) 0.0307(8) 0.0036(7) 0.0087(6) 0.0012(7) C15 0.0404(9) 0.0555(11) 0.0419(9) -0.0006(8) 0.0135(8) 0.0047(8) C16 0.0714(14) 0.0531(12) 0.0682(13) -0.0077(10) 0.0335(11) -0.0133(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 C1 O1 H1 109.5 C8 O4 C9 118.33(12) O2 C1 O1 122.65(15) O2 C1 C2 121.50(14) O1 C1 C2 115.84(14) C3 C2 C7 120.03(15) C3 C2 C1 121.19(14) C7 C2 C1 118.78(14) C4 C3 C2 120.27(15) C4 C3 H3 119.9 C2 C3 H3 119.9 C3 C4 C5 119.91(15) C3 C4 H4 120.0 C5 C4 H4 120.0 C4 C5 C6 120.44(15) C4 C5 H5 119.8 C6 C5 H5 119.8 C7 C6 C5 119.71(14) C7 C6 C8 122.18(14) C5 C6 C8 118.11(14) C6 C7 C2 119.65(15) C6 C7 H7 120.2 C2 C7 H7 120.2 O3 C8 O4 122.75(15) O3 C8 C6 125.75(15) O4 C8 C6 111.49(13) C10 C9 C14 121.90(14) C10 C9 O4 117.60(14) C14 C9 O4 120.23(15) C9 C10 C11 119.60(17) C9 C10 H10 120.2 C11 C10 H10 120.2 C12 C11 C10 119.96(18) C12 C11 H11 120.0 C10 C11 H11 120.0 C13 C12 C11 119.85(16) C13 C12 H12 120.1 C11 C12 H12 120.1 C12 C13 C14 122.08(17) C12 C13 H13 119.0 C14 C13 H13 119.0 C9 C14 C13 116.61(16) C9 C14 C15 126.71(14) C13 C14 C15 116.68(15) O5 C15 C16 119.23(18) O5 C15 C14 118.82(16) C16 C15 C14 121.95(15) C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C1 1.2946(19) O1 H1 0.8200 O2 C1 1.236(2) O3 C8 1.1953(19) O4 C8 1.3587(19) O4 C9 1.4111(17) O5 C15 1.215(2) C1 C2 1.485(2) C2 C3 1.387(2) C2 C7 1.395(2) C3 C4 1.379(2) C3 H3 0.9300 C4 C5 1.382(2) C4 H4 0.9300 C5 C6 1.393(2) C5 H5 0.9300 C6 C7 1.386(2) C6 C8 1.489(2) C7 H7 0.9300 C9 C10 1.382(2) C9 C14 1.394(2) C10 C11 1.385(2) C10 H10 0.9300 C11 C12 1.379(3) C11 H11 0.9300 C12 C13 1.372(3) C12 H12 0.9300 C13 C14 1.402(2) C13 H13 0.9300 C14 C15 1.502(2) C15 C16 1.493(2) C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 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 O1 H1 O2 3_656 0.82 1.84 2.6623(18) 175 yes C4 H4 O5 4_566 0.93 2.58 3.257(3) 130 yes 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 O2 C1 C2 C3 -179.32(18) O1 C1 C2 C3 1.4(3) O2 C1 C2 C7 1.2(3) O1 C1 C2 C7 -178.08(17) C7 C2 C3 C4 0.4(3) C1 C2 C3 C4 -179.14(17) C2 C3 C4 C5 -0.6(3) C3 C4 C5 C6 0.4(3) C4 C5 C6 C7 0.0(3) C4 C5 C6 C8 179.31(17) C5 C6 C7 C2 -0.3(3) C8 C6 C7 C2 -179.53(15) C3 C2 C7 C6 0.1(2) C1 C2 C7 C6 179.60(15) C9 O4 C8 O3 -5.1(3) C9 O4 C8 C6 175.91(14) C7 C6 C8 O3 -175.87(18) C5 C6 C8 O3 4.9(3) C7 C6 C8 O4 3.1(2) C5 C6 C8 O4 -176.17(15) C8 O4 C9 C10 -74.90(19) C8 O4 C9 C14 110.95(17) C14 C9 C10 C11 0.3(3) O4 C9 C10 C11 -173.72(15) C9 C10 C11 C12 -0.8(3) C10 C11 C12 C13 0.5(3) C11 C12 C13 C14 0.2(3) C10 C9 C14 C13 0.4(2) O4 C9 C14 C13 174.31(13) C10 C9 C14 C15 -179.79(16) O4 C9 C14 C15 -5.9(2) C12 C13 C14 C9 -0.7(2) C12 C13 C14 C15 179.48(16) C9 C14 C15 O5 170.50(17) C13 C14 C15 O5 -9.7(2) C9 C14 C15 C16 -9.6(3) C13 C14 C15 C16 170.19(17) _cod_database_fobs_code 2240070