#------------------------------------------------------------------------------ #$Date: 2019-11-16 04:09:10 +0200 (Sat, 16 Nov 2019) $ #$Revision: 227924 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/72/7157203.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7157203 loop_ _publ_author_name 'Neog, Kashmiri' 'Das, Babulal' 'Gogoi, Pranjal' _publ_section_title ; 2,3-Diaroyl benzofurans from arynes: sequential synthesis of 2-aroyl benzofurans followed by benzoylation. ; _journal_issue 17 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3138 _journal_page_last 3150 _journal_paper_doi 10.1039/c8ob00631h _journal_volume 16 _journal_year 2018 _chemical_compound_source synthetic _chemical_formula_sum 'C23 H16 O3' _chemical_formula_weight 340.36 _chemical_melting_point 111.5(15) _chemical_name_common KN-415 _chemical_name_systematic (3-Benzoylbenzofuran-2-yl)(p-tolyl)methanone _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-02-14 deposited with the CCDC. 2018-04-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.222(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.6469(6) _cell_length_b 11.4426(8) _cell_length_c 19.7800(13) _cell_measurement_reflns_used 2207 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.000 _cell_measurement_theta_min 2.057 _cell_volume 1728.0(2) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0461 _diffrn_reflns_av_unetI/netI 0.0263 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 25141 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.057 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.308 _exptl_crystal_description plates _exptl_crystal_F_000 712 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: ethyl acetate-Hexanes' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.169 _refine_diff_density_min -0.182 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3011 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.056 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0447 _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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1371 _refine_ls_wR_factor_ref 0.1521 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2207 _reflns_number_total 3011 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c8ob00631h2.cif _cod_data_source_block KN-415 _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '110-113' was changed to '111.5(15)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius ; _cod_database_code 7157203 _shelx_shelxl_version_number 2014/7 _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 ; KN-415.res created by SHELXL-2014/7 TITL KN-415 in P2(1)/c CELL 0.71073 7.6469 11.4426 19.7800 90.000 93.222 90.000 ZERR 4.00 0.0006 0.0008 0.0013 0.000 0.005 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H O UNIT 92 64 12 OMIT -3 50 L.S. 20 ACTA BOND FMAP 2 PLAN 4 TEMP 23.000 WGHT 0.100000 FVAR 0.47424 MOLE 1 O1 3 0.292673 0.973717 0.425380 11.00000 0.07480 0.04879 = 0.04851 0.00470 0.00698 0.00671 O2 3 0.351651 0.737725 0.540290 11.00000 0.11281 0.05738 = 0.05528 0.00822 0.01107 0.02708 O3 3 0.579877 0.640293 0.404857 11.00000 0.06718 0.07019 = 0.08479 0.00263 0.01441 0.01724 C10 1 0.370360 0.788147 0.401899 11.00000 0.05921 0.05467 = 0.04656 0.00231 0.00615 0.00939 C18 1 0.292823 0.571170 0.414520 11.00000 0.06482 0.05607 = 0.03956 -0.00353 0.00676 0.01085 C5 1 0.251638 0.922620 0.573658 11.00000 0.05240 0.04976 = 0.04621 0.00116 0.00375 0.00223 C8 1 0.311432 0.837790 0.523360 11.00000 0.06288 0.04700 = 0.05021 0.00384 0.00585 0.00810 C17 1 0.425565 0.662945 0.408456 11.00000 0.06553 0.05787 = 0.04253 -0.00112 0.00673 0.01538 C9 1 0.325081 0.863225 0.450879 11.00000 0.06473 0.04968 = 0.04580 0.00652 0.00779 0.00954 C6 1 0.223783 1.039648 0.562007 11.00000 0.08343 0.05451 = 0.05408 0.00459 0.01619 0.01036 AFIX 43 H6 2 0.236777 1.070162 0.519001 11.00000 -1.20000 AFIX 0 C16 1 0.318113 0.967011 0.357517 11.00000 0.06268 0.05675 = 0.04295 0.00504 0.00396 -0.00132 C11 1 0.367442 0.854586 0.340330 11.00000 0.05524 0.06016 = 0.04629 0.00490 0.00439 0.00295 C2 1 0.153034 1.071339 0.677781 11.00000 0.05548 0.06080 = 0.05671 -0.00951 0.00807 -0.00407 C4 1 0.227727 0.880633 0.638338 11.00000 0.10213 0.05426 = 0.04895 0.00397 0.00880 0.00572 AFIX 43 H4 2 0.244848 0.801638 0.647579 11.00000 -1.20000 AFIX 0 C19 1 0.345318 0.457567 0.428844 11.00000 0.08175 0.05961 = 0.05030 -0.00040 0.00479 0.01123 AFIX 43 H19 2 0.464003 0.440556 0.435317 11.00000 -1.20000 AFIX 0 C12 1 0.400267 0.830333 0.272943 11.00000 0.06370 0.07308 = 0.04925 -0.00174 0.00707 0.00398 AFIX 43 H12 2 0.434471 0.756133 0.259764 11.00000 -1.20000 AFIX 0 C3 1 0.179244 0.953983 0.688758 11.00000 0.09942 0.07112 = 0.04720 -0.00132 0.01350 -0.00137 AFIX 43 H3 2 0.163668 0.923448 0.731576 11.00000 -1.20000 AFIX 0 C15 1 0.298564 1.056911 0.311813 11.00000 0.08449 0.05826 = 0.05522 0.00899 0.00487 -0.00359 AFIX 43 H15 2 0.265314 1.131460 0.324731 11.00000 -1.20000 AFIX 0 C13 1 0.380362 0.919493 0.227011 11.00000 0.07659 0.09008 = 0.04418 0.00788 0.00760 -0.00818 AFIX 43 H13 2 0.400601 0.905179 0.181832 11.00000 -1.20000 AFIX 0 C14 1 0.330674 1.030783 0.246278 11.00000 0.08609 0.07141 = 0.05885 0.01913 0.00169 -0.01134 AFIX 43 H14 2 0.318920 1.089190 0.213643 11.00000 -1.20000 AFIX 0 C7 1 0.176454 1.112651 0.613840 11.00000 0.08621 0.05357 = 0.06891 0.00093 0.01591 0.00888 AFIX 43 H7 2 0.160131 1.191848 0.605006 11.00000 -1.20000 AFIX 0 C20 1 0.224724 0.370112 0.433583 11.00000 0.10845 0.06258 = 0.06565 -0.00027 0.00795 -0.00184 AFIX 43 H20 2 0.261178 0.294060 0.443152 11.00000 -1.20000 AFIX 0 C23 1 0.115207 0.594539 0.404817 11.00000 0.07337 0.07424 = 0.06312 -0.00265 0.00231 0.01282 AFIX 43 H23 2 0.077858 0.670305 0.394967 11.00000 -1.20000 AFIX 0 C21 1 0.049284 0.395315 0.424113 11.00000 0.10148 0.09206 = 0.06815 -0.00961 0.01088 -0.02487 AFIX 43 H21 2 -0.032787 0.335949 0.427590 11.00000 -1.20000 AFIX 0 C22 1 -0.006028 0.506774 0.409625 11.00000 0.07253 0.10345 = 0.07601 -0.01010 0.00388 -0.00477 AFIX 43 H22 2 -0.124951 0.522976 0.403079 11.00000 -1.20000 AFIX 0 C1 1 0.104852 1.151232 0.733973 11.00000 0.08219 0.08277 = 0.07297 -0.02449 0.01501 -0.00243 AFIX 137 H1A 2 -0.012195 1.134177 0.746165 11.00000 -1.50000 H1B 2 0.111133 1.230919 0.719122 11.00000 -1.50000 H1C 2 0.184800 1.139699 0.772571 11.00000 -1.50000 AFIX 0 HKLF 4 REM KN-415 in P2(1)/c REM R1 = 0.0447 for 2207 Fo > 4sig(Fo) and 0.0624 for all 3011 data REM 236 parameters refined using 0 restraints END WGHT 0.0666 0.2016 REM Highest difference peak 0.169, deepest hole -0.182, 1-sigma level 0.035 Q1 1 -0.0108 1.2179 0.7162 11.00000 0.05 0.17 Q2 1 0.0475 1.0873 0.7765 11.00000 0.05 0.13 Q3 1 0.2303 1.2052 0.7504 11.00000 0.05 0.13 Q4 1 0.3708 1.0759 0.5286 11.00000 0.05 0.12 ; _shelx_res_checksum 83720 loop_ _space_group_symop_operation_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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp O1 O 0.29267(17) 0.97372(10) 0.42538(6) 0.0572(3) Uani 1 1 d . . O2 O 0.3517(2) 0.73772(11) 0.54029(6) 0.0749(4) Uani 1 1 d . . O3 O 0.57988(19) 0.64029(12) 0.40486(7) 0.0737(4) Uani 1 1 d . . C10 C 0.3704(2) 0.78815(15) 0.40190(8) 0.0534(5) Uani 1 1 d . . C18 C 0.2928(2) 0.57117(15) 0.41452(8) 0.0533(4) Uani 1 1 d . . C5 C 0.2516(2) 0.92262(14) 0.57366(8) 0.0494(4) Uani 1 1 d . . C8 C 0.3114(2) 0.83779(15) 0.52336(8) 0.0533(4) Uani 1 1 d . . C17 C 0.4256(3) 0.66295(15) 0.40846(8) 0.0552(5) Uani 1 1 d . . C9 C 0.3251(2) 0.86323(14) 0.45088(8) 0.0532(5) Uani 1 1 d . . C6 C 0.2238(3) 1.03965(16) 0.56201(9) 0.0635(5) Uani 1 1 d . . H6 H 0.2368 1.0702 0.5190 0.076 Uiso 1 1 calc R U C16 C 0.3181(2) 0.96701(15) 0.35752(8) 0.0541(5) Uani 1 1 d . . C11 C 0.3674(2) 0.85459(15) 0.34033(9) 0.0538(4) Uani 1 1 d . . C2 C 0.1530(2) 1.07134(15) 0.67778(9) 0.0575(5) Uani 1 1 d . . C4 C 0.2277(3) 0.88063(17) 0.63834(9) 0.0683(5) Uani 1 1 d . . H4 H 0.2448 0.8016 0.6476 0.082 Uiso 1 1 calc R U C19 C 0.3453(3) 0.45757(17) 0.42884(9) 0.0638(5) Uani 1 1 d . . H19 H 0.4640 0.4406 0.4353 0.077 Uiso 1 1 calc R U C12 C 0.4003(2) 0.83033(18) 0.27294(9) 0.0619(5) Uani 1 1 d . . H12 H 0.4345 0.7561 0.2598 0.074 Uiso 1 1 calc R U C3 C 0.1792(3) 0.95398(18) 0.68876(10) 0.0722(6) Uani 1 1 d . . H3 H 0.1637 0.9234 0.7316 0.087 Uiso 1 1 calc R U C15 C 0.2986(3) 1.05691(16) 0.31181(10) 0.0660(5) Uani 1 1 d . . H15 H 0.2653 1.1315 0.3247 0.079 Uiso 1 1 calc R U C13 C 0.3804(3) 0.9195(2) 0.22701(10) 0.0701(6) Uani 1 1 d . . H13 H 0.4006 0.9052 0.1818 0.084 Uiso 1 1 calc R U C14 C 0.3307(3) 1.03078(19) 0.24628(10) 0.0722(6) Uani 1 1 d . . H14 H 0.3189 1.0892 0.2136 0.087 Uiso 1 1 calc R U C7 C 0.1765(3) 1.11265(17) 0.61384(10) 0.0691(6) Uani 1 1 d . . H7 H 0.1601 1.1918 0.6050 0.083 Uiso 1 1 calc R U C20 C 0.2247(4) 0.37011(19) 0.43358(11) 0.0788(6) Uani 1 1 d . . H20 H 0.2612 0.2941 0.4432 0.095 Uiso 1 1 calc R U C23 C 0.1152(3) 0.59454(19) 0.40482(10) 0.0703(6) Uani 1 1 d . . H23 H 0.0779 0.6703 0.3950 0.084 Uiso 1 1 calc R U C21 C 0.0493(4) 0.3953(2) 0.42411(12) 0.0870(7) Uani 1 1 d . . H21 H -0.0328 0.3359 0.4276 0.104 Uiso 1 1 calc R U C22 C -0.0060(3) 0.5068(2) 0.40963(12) 0.0840(7) Uani 1 1 d . . H22 H -0.1250 0.5230 0.4031 0.101 Uiso 1 1 calc R U C1 C 0.1049(3) 1.15123(19) 0.73397(11) 0.0789(6) Uani 1 1 d . . H1A H -0.0122 1.1342 0.7462 0.118 Uiso 1 1 calc R U H1B H 0.1111 1.2309 0.7191 0.118 Uiso 1 1 calc R U H1C H 0.1848 1.1397 0.7726 0.118 Uiso 1 1 calc R U loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0748(9) 0.0488(7) 0.0485(7) 0.0047(5) 0.0070(5) 0.0067(5) O2 0.1128(12) 0.0574(8) 0.0553(8) 0.0082(6) 0.0111(7) 0.0271(7) O3 0.0672(10) 0.0702(9) 0.0848(10) 0.0026(7) 0.0144(7) 0.0172(7) C10 0.0592(11) 0.0547(10) 0.0466(10) 0.0023(8) 0.0061(7) 0.0094(7) C18 0.0648(12) 0.0561(11) 0.0396(9) -0.0035(7) 0.0068(7) 0.0109(8) C5 0.0524(10) 0.0498(10) 0.0462(10) 0.0012(7) 0.0037(7) 0.0022(7) C8 0.0629(11) 0.0470(10) 0.0502(10) 0.0038(8) 0.0058(8) 0.0081(7) C17 0.0655(13) 0.0579(11) 0.0425(10) -0.0011(8) 0.0067(7) 0.0154(9) C9 0.0647(12) 0.0497(10) 0.0458(10) 0.0065(7) 0.0078(7) 0.0095(8) C6 0.0834(14) 0.0545(11) 0.0541(11) 0.0046(8) 0.0162(9) 0.0104(9) C16 0.0627(12) 0.0567(10) 0.0430(10) 0.0050(8) 0.0040(7) -0.0013(8) C11 0.0552(11) 0.0602(11) 0.0463(10) 0.0049(8) 0.0044(7) 0.0029(8) C2 0.0555(11) 0.0608(11) 0.0567(11) -0.0095(8) 0.0081(8) -0.0041(8) C4 0.1021(16) 0.0543(11) 0.0489(11) 0.0040(8) 0.0088(10) 0.0057(10) C19 0.0817(14) 0.0596(12) 0.0503(11) -0.0004(8) 0.0048(9) 0.0112(9) C12 0.0637(12) 0.0731(12) 0.0493(11) -0.0017(9) 0.0071(8) 0.0040(9) C3 0.0994(17) 0.0711(13) 0.0472(11) -0.0013(9) 0.0135(9) -0.0014(11) C15 0.0845(14) 0.0583(11) 0.0552(12) 0.0090(9) 0.0049(9) -0.0036(9) C13 0.0766(14) 0.0901(16) 0.0442(11) 0.0079(10) 0.0076(9) -0.0082(11) C14 0.0861(15) 0.0714(13) 0.0589(12) 0.0191(10) 0.0017(10) -0.0113(10) C7 0.0862(15) 0.0536(11) 0.0689(13) 0.0009(9) 0.0159(10) 0.0089(9) C20 0.108(2) 0.0626(13) 0.0656(14) -0.0003(9) 0.0080(12) -0.0018(12) C23 0.0734(15) 0.0742(13) 0.0631(12) -0.0026(10) 0.0023(9) 0.0128(11) C21 0.101(2) 0.0921(18) 0.0681(14) -0.0096(12) 0.0109(12) -0.0249(14) C22 0.0725(15) 0.1035(19) 0.0760(15) -0.0101(13) 0.0039(11) -0.0048(13) C1 0.0822(15) 0.0828(14) 0.0730(14) -0.0245(11) 0.0150(11) -0.0024(11) 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 C16 O1 C9 105.95(12) C9 C10 C11 106.18(15) C9 C10 C17 128.84(15) C11 C10 C17 124.85(15) C19 C18 C23 118.66(19) C19 C18 C17 119.58(17) C23 C18 C17 121.75(17) C6 C5 C4 117.70(16) C6 C5 C8 125.26(15) C4 C5 C8 117.00(15) O2 C8 C9 114.82(15) O2 C8 C5 120.69(15) C9 C8 C5 124.48(15) O3 C17 C18 122.01(16) O3 C17 C10 118.00(17) C18 C17 C10 119.87(16) C10 C9 O1 111.59(14) C10 C9 C8 127.31(15) O1 C9 C8 121.09(14) C5 C6 C7 120.53(17) O1 C16 C15 125.99(16) O1 C16 C11 110.34(14) C15 C16 C11 123.67(17) C16 C11 C12 118.90(16) C16 C11 C10 105.94(15) C12 C11 C10 135.16(17) C7 C2 C3 117.22(17) C7 C2 C1 121.55(18) C3 C2 C1 121.21(18) C3 C4 C5 120.91(18) C20 C19 C18 120.8(2) C13 C12 C11 117.75(18) C4 C3 C2 121.80(18) C14 C15 C16 116.26(18) C12 C13 C14 121.56(19) C15 C14 C13 121.86(18) C2 C7 C6 121.83(19) C19 C20 C21 119.6(2) C22 C23 C18 120.6(2) C22 C21 C20 120.8(2) C21 C22 C23 119.6(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C16 1.369(2) O1 C9 1.3785(19) O2 C8 1.2273(19) O3 C17 1.214(2) C10 C9 1.354(2) C10 C11 1.435(2) C10 C17 1.497(2) C18 C19 1.385(3) C18 C23 1.387(3) C18 C17 1.470(3) C5 C6 1.373(2) C5 C4 1.388(2) C5 C8 1.481(2) C8 C9 1.472(2) C6 C7 1.386(3) C16 C15 1.372(3) C16 C11 1.388(2) C11 C12 1.398(2) C2 C7 1.371(3) C2 C3 1.373(3) C2 C1 1.501(3) C4 C3 1.370(3) C19 C20 1.368(3) C12 C13 1.369(3) C15 C14 1.366(3) C13 C14 1.388(3) C20 C21 1.375(4) C23 C22 1.374(3) C21 C22 1.369(3)