#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:11:10 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257961 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/04/7240401.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_7240401 loop_ _publ_author_name 'Al-Zoubi, Raed M.' 'Al-Omari, Mothana K.' 'Al-Jammal, Walid K.' 'Ferguson, Michael J.' _publ_section_title ; Palladium-catalyzed highly regioselective mono and double Sonogashira cross-coupling reactions of 5-substituted-1,2,3-triiodobenzene under ambient conditions ; _journal_issue 28 _journal_name_full 'RSC Advances' _journal_page_first 16366 _journal_page_last 16376 _journal_paper_doi 10.1039/D0RA01569E _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C15 H9 F I2 O' _chemical_formula_sum 'C15 H9 F I2 O' _chemical_formula_weight 478.02 _chemical_name_systematic ; 5-fluoro-1,2-diiodo-3-[(4-methoxyphenyl)ethynyl]benzene ; _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2020-02-05 deposited with the CCDC. 2020-04-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.15290(8) _cell_length_b 11.4859(2) _cell_length_c 30.5943(6) _cell_measurement_reflns_used 9894 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 73.63 _cell_measurement_theta_min 4.11 _cell_volume 1459.34(5) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT-2014/5 (Sheldrick 2015)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_unetI/netI 0.0222 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_number 9797 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 74.087 _diffrn_reflns_theta_min 2.889 _exptl_absorpt_coefficient_mu 33.866 _exptl_absorpt_correction_T_max 0.1121 _exptl_absorpt_correction_T_min 0.0046 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 2.176 _exptl_crystal_description plate _exptl_crystal_F_000 888 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: hexanes/dichloromethane' _exptl_crystal_size_max 0.158 _exptl_crystal_size_mid 0.127 _exptl_crystal_size_min 0.028 _refine_diff_density_max 0.305 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.058 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.037(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2934 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.112 _refine_ls_R_factor_all 0.0150 _refine_ls_R_factor_gt 0.0149 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0147P)^2^+0.2798P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0380 _reflns_Friedel_coverage 0.657 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.995 _reflns_number_gt 2918 _reflns_number_total 2934 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra01569e2.cif _cod_data_source_block jus1809 _cod_depositor_comments 'Adding full bibliography for 7240398--7240401.cif.' _cod_original_cell_volume 1459.35(5) _cod_database_code 7240401 _shelx_shelxl_version_number 2017/1 _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_estimated_absorpt_t_min 0.075 _shelx_estimated_absorpt_t_max 0.451 _shelx_res_file ; TITL jus1809 in P2(1)2(1)2(1) jus1809.res created by SHELXL-2017/1 at 11:16:24 on 30-Nov-2018 CELL 1.54178 4.15290 11.48594 30.59427 90.0000 90.0000 90.0000 ZERR 4.00 0.00008 0.00024 0.00060 0.0000 0.0000 0.0000 LATT -1 SYMM 0.5-X, -Y, 0.5+Z SYMM -X, 0.5+Y, 0.5-Z SYMM 0.5+X, 0.5-Y, -Z SFAC C H O F I UNIT 60 36 4 4 8 TEMP -100.000 SIZE 0.028 0.127 0.158 L.S. 4 ACTA CONF TWIN WGHT 0.014700 0.279800 BASF 0.03682 FVAR 0.10600 I1 5 -0.069739 0.634477 0.528208 11.00000 0.03646 0.06050 = 0.05750 0.02345 -0.00046 0.00104 I2 5 0.247433 0.674500 0.638473 11.00000 0.04044 0.03703 = 0.06441 -0.00208 -0.00114 0.00220 F1 4 0.299048 0.194784 0.546333 11.00000 0.11463 0.05209 = 0.05028 -0.01384 -0.00081 0.01149 O1 3 1.115962 0.573892 0.871189 11.00000 0.07599 0.04823 = 0.04396 -0.00382 -0.00766 -0.00781 C1 1 0.146875 0.500059 0.564172 11.00000 0.03347 0.04364 = 0.04325 0.01124 0.00231 0.00013 C2 1 0.275488 0.515905 0.605703 11.00000 0.03553 0.03705 = 0.04304 0.00391 0.00552 -0.00008 C3 1 0.426247 0.421106 0.627184 11.00000 0.04066 0.03959 = 0.03803 0.00312 0.00715 0.00264 C4 1 0.435867 0.311869 0.606241 11.00000 0.05958 0.04082 = 0.04059 0.00373 0.00804 0.00538 AFIX 43 H4 2 0.535828 0.246984 0.619904 11.00000 -1.20000 AFIX 0 C5 1 0.298212 0.301286 0.565830 11.00000 0.06734 0.04578 = 0.03911 -0.00412 0.00646 0.00355 C6 1 0.156124 0.391453 0.543783 11.00000 0.05664 0.05685 = 0.03517 0.00299 0.00099 -0.00158 AFIX 43 H6 2 0.066699 0.380400 0.515506 11.00000 -1.20000 AFIX 0 C7 1 0.564017 0.434463 0.669672 11.00000 0.04344 0.03772 = 0.04317 0.00347 0.00641 0.00291 C8 1 0.676434 0.448751 0.705082 11.00000 0.04553 0.03933 = 0.04289 0.00316 0.00427 0.00081 C9 1 0.799175 0.477136 0.747671 11.00000 0.04151 0.04174 = 0.03957 0.00167 0.00527 -0.00038 C10 1 0.969153 0.397279 0.772664 11.00000 0.04889 0.03805 = 0.04376 -0.00177 0.00273 0.00071 AFIX 43 H10 2 1.009023 0.321629 0.761338 11.00000 -1.20000 AFIX 0 C11 1 1.081898 0.426239 0.813982 11.00000 0.04568 0.04003 = 0.04309 0.00386 -0.00046 -0.00270 AFIX 43 H11 2 1.198483 0.370867 0.830762 11.00000 -1.20000 AFIX 0 C12 1 1.022706 0.537360 0.830703 11.00000 0.04575 0.04238 = 0.04138 0.00032 0.00342 -0.00899 C13 1 0.856305 0.618912 0.805597 11.00000 0.05893 0.03622 = 0.04903 -0.00271 0.00263 -0.00112 AFIX 43 H13 2 0.819425 0.694991 0.816703 11.00000 -1.20000 AFIX 0 C14 1 0.745090 0.588885 0.764521 11.00000 0.04766 0.04004 = 0.04734 0.00316 0.00311 0.00289 AFIX 43 H14 2 0.630933 0.644532 0.747562 11.00000 -1.20000 AFIX 0 C15 1 1.257135 0.489610 0.899851 11.00000 0.07712 0.05759 = 0.05030 0.00430 -0.01356 -0.01215 AFIX 137 H15A 2 1.286659 0.524056 0.928881 11.00000 -1.20000 H15B 2 1.466455 0.465302 0.888212 11.00000 -1.20000 H15C 2 1.114923 0.421781 0.902078 11.00000 -1.20000 AFIX 0 HKLF 4 REM jus1809 in P2(1)2(1)2(1) REM R1 = 0.0149 for 2918 Fo > 4sig(Fo) and 0.0150 for all 2934 data REM 174 parameters refined using 0 restraints END WGHT 0.0147 0.2792 REM Highest difference peak 0.305, deepest hole -0.294, 1-sigma level 0.058 Q1 1 -0.1613 0.5693 0.5288 11.00000 0.05 0.31 Q2 1 0.2390 0.7305 0.6150 11.00000 0.05 0.29 Q3 1 0.3382 0.7417 0.6270 11.00000 0.05 0.27 Q4 1 0.2067 0.6215 0.6161 11.00000 0.05 0.25 Q5 1 -0.0590 0.6328 0.5547 11.00000 0.05 0.25 Q6 1 0.0306 0.5671 0.5479 11.00000 0.05 0.24 Q7 1 0.2196 0.6560 0.6129 11.00000 0.05 0.24 Q8 1 0.4122 0.3738 0.6201 11.00000 0.05 0.21 Q9 1 0.3449 0.4600 0.6183 11.00000 0.05 0.21 Q10 1 -0.0717 0.5808 0.5017 11.00000 0.05 0.20 Q11 1 -0.0780 0.6886 0.4953 11.00000 0.05 0.19 Q12 1 0.0810 0.7963 0.5517 11.00000 0.05 0.18 Q13 1 -0.1911 0.6833 0.5257 11.00000 0.05 0.17 Q14 1 0.3734 0.2518 0.6223 11.00000 0.05 0.17 Q15 1 0.8795 0.5831 0.8230 11.00000 0.05 0.17 Q16 1 0.2685 0.7378 0.5546 11.00000 0.05 0.17 Q17 1 0.9979 0.4789 0.8248 11.00000 0.05 0.17 Q18 1 0.6040 0.7384 0.6062 11.00000 0.05 0.16 Q19 1 0.5231 0.2183 0.5482 11.00000 0.05 0.15 Q20 1 -0.0936 0.6999 0.4461 11.00000 0.05 0.15 ; _shelx_res_checksum 20589 loop_ _space_group_symop_operation_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_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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I -0.06974(6) 0.63448(2) 0.52821(2) 0.05149(8) Uani 1 1 d . . . . . I2 I 0.24743(6) 0.67450(2) 0.63847(2) 0.04729(7) Uani 1 1 d . . . . . F1 F 0.2990(10) 0.1948(2) 0.54633(8) 0.0723(9) Uani 1 1 d . . . . . O1 O 1.1160(9) 0.5739(3) 0.87119(9) 0.0561(7) Uani 1 1 d . . . . . C1 C 0.1469(8) 0.5001(3) 0.56417(11) 0.0401(7) Uani 1 1 d . . . . . C2 C 0.2755(9) 0.5159(3) 0.60570(10) 0.0385(6) Uani 1 1 d . . . . . C3 C 0.4262(10) 0.4211(3) 0.62718(10) 0.0394(7) Uani 1 1 d . . . . . C4 C 0.4359(11) 0.3119(3) 0.60624(11) 0.0470(8) Uani 1 1 d . . . . . H4 H 0.535828 0.246984 0.619904 0.056 Uiso 1 1 calc R U . . . C5 C 0.2982(12) 0.3013(3) 0.56583(12) 0.0507(9) Uani 1 1 d . . . . . C6 C 0.1561(10) 0.3915(4) 0.54378(11) 0.0496(9) Uani 1 1 d . . . . . H6 H 0.066699 0.380400 0.515506 0.059 Uiso 1 1 calc R U . . . C7 C 0.5640(10) 0.4345(3) 0.66967(11) 0.0414(7) Uani 1 1 d . . . . . C8 C 0.6764(9) 0.4488(3) 0.70508(11) 0.0426(8) Uani 1 1 d . . . . . C9 C 0.7992(9) 0.4771(3) 0.74767(11) 0.0409(7) Uani 1 1 d . . . . . C10 C 0.9692(10) 0.3973(3) 0.77266(11) 0.0436(8) Uani 1 1 d . . . . . H10 H 1.009023 0.321629 0.761338 0.052 Uiso 1 1 calc R U . . . C11 C 1.0819(11) 0.4262(3) 0.81398(11) 0.0429(7) Uani 1 1 d . . . . . H11 H 1.198483 0.370867 0.830762 0.052 Uiso 1 1 calc R U . . . C12 C 1.0227(10) 0.5374(3) 0.83070(11) 0.0432(8) Uani 1 1 d . . . . . C13 C 0.8563(10) 0.6189(3) 0.80560(13) 0.0481(9) Uani 1 1 d . . . . . H13 H 0.819425 0.694991 0.816703 0.058 Uiso 1 1 calc R U . . . C14 C 0.7451(12) 0.5889(3) 0.76452(11) 0.0450(7) Uani 1 1 d . . . . . H14 H 0.630933 0.644532 0.747562 0.054 Uiso 1 1 calc R U . . . C15 C 1.2571(15) 0.4896(4) 0.89985(13) 0.0617(11) Uani 1 1 d . . . . . H15A H 1.286659 0.524056 0.928881 0.074 Uiso 1 1 calc R U . . . H15B H 1.466455 0.465302 0.888212 0.074 Uiso 1 1 calc R U . . . H15C H 1.114923 0.421781 0.902078 0.074 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 I1 0.03646(11) 0.06050(15) 0.05750(12) 0.02345(11) -0.00046(11) 0.00104(11) I2 0.04044(11) 0.03703(11) 0.06441(13) -0.00208(9) -0.00114(11) 0.00220(10) F1 0.115(3) 0.0521(14) 0.0503(12) -0.0138(10) -0.0008(14) 0.0115(16) O1 0.076(2) 0.0482(15) 0.0440(13) -0.0038(11) -0.0077(14) -0.0078(15) C1 0.0335(16) 0.0436(19) 0.0433(16) 0.0112(13) 0.0023(12) 0.0001(13) C2 0.0355(16) 0.0370(16) 0.0430(15) 0.0039(12) 0.0055(14) -0.0001(15) C3 0.0407(16) 0.0396(17) 0.0380(14) 0.0031(12) 0.0071(14) 0.0026(16) C4 0.060(2) 0.0408(19) 0.0406(16) 0.0037(13) 0.0080(17) 0.0054(19) C5 0.067(3) 0.046(2) 0.0391(16) -0.0041(13) 0.0065(17) 0.0035(19) C6 0.057(2) 0.057(2) 0.0352(14) 0.0030(14) 0.0010(14) -0.0016(17) C7 0.0434(18) 0.0377(17) 0.0432(16) 0.0035(12) 0.0064(15) 0.0029(17) C8 0.046(2) 0.0393(18) 0.0429(17) 0.0032(13) 0.0043(13) 0.0008(14) C9 0.0415(18) 0.0417(17) 0.0396(15) 0.0017(12) 0.0053(14) -0.0004(14) C10 0.049(2) 0.0380(18) 0.0438(16) -0.0018(13) 0.0027(14) 0.0007(15) C11 0.0457(19) 0.0400(18) 0.0431(16) 0.0039(13) -0.0005(16) -0.0027(17) C12 0.046(2) 0.0424(19) 0.0414(16) 0.0003(13) 0.0034(13) -0.0090(15) C13 0.059(2) 0.0362(19) 0.0490(17) -0.0027(14) 0.0026(16) -0.0011(16) C14 0.0477(19) 0.0400(17) 0.0473(16) 0.0032(13) 0.0031(17) 0.0029(18) C15 0.077(3) 0.058(2) 0.050(2) 0.0043(16) -0.014(2) -0.012(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.3257 6.8362 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 O1 C15 117.7(3) . . ? C2 C1 C6 121.0(3) . . ? C2 C1 I1 123.2(3) . . ? C6 C1 I1 115.8(3) . . ? C1 C2 C3 119.5(3) . . ? C1 C2 I2 122.2(3) . . ? C3 C2 I2 118.3(2) . . ? C4 C3 C2 119.0(3) . . ? C4 C3 C7 119.9(3) . . ? C2 C3 C7 121.1(3) . . ? C5 C4 C3 118.6(4) . . ? F1 C5 C4 118.4(4) . . ? F1 C5 C6 117.7(4) . . ? C4 C5 C6 123.9(4) . . ? C5 C6 C1 117.9(3) . . ? C8 C7 C3 178.2(4) . . ? C7 C8 C9 174.5(4) . . ? C10 C9 C14 119.0(3) . . ? C10 C9 C8 122.0(3) . . ? C14 C9 C8 119.0(3) . . ? C9 C10 C11 121.0(3) . . ? C10 C11 C12 119.5(4) . . ? O1 C12 C13 115.7(3) . . ? O1 C12 C11 124.3(4) . . ? C13 C12 C11 119.9(3) . . ? C14 C13 C12 119.9(4) . . ? C13 C14 C9 120.6(4) . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C1 2.098(3) . ? I2 C2 2.083(3) . ? F1 C5 1.361(5) . ? O1 C12 1.364(4) . ? O1 C15 1.432(5) . ? C1 C2 1.390(5) . ? C1 C6 1.395(6) . ? C2 C3 1.418(5) . ? C3 C4 1.409(5) . ? C3 C7 1.429(5) . ? C4 C5 1.368(6) . ? C5 C6 1.370(6) . ? C7 C8 1.191(5) . ? C8 C9 1.437(5) . ? C9 C10 1.387(5) . ? C9 C14 1.401(5) . ? C10 C11 1.388(5) . ? C11 C12 1.397(5) . ? C12 C13 1.395(6) . ? C13 C14 1.383(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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.8(5) . . . . ? I1 C1 C2 C3 -178.1(3) . . . . ? C6 C1 C2 I2 -177.1(3) . . . . ? I1 C1 C2 I2 3.1(4) . . . . ? C1 C2 C3 C4 -1.4(6) . . . . ? I2 C2 C3 C4 177.4(3) . . . . ? C1 C2 C3 C7 179.3(3) . . . . ? I2 C2 C3 C7 -1.8(5) . . . . ? C2 C3 C4 C5 -0.1(6) . . . . ? C7 C3 C4 C5 179.1(4) . . . . ? C3 C4 C5 F1 -177.9(4) . . . . ? C3 C4 C5 C6 1.4(7) . . . . ? F1 C5 C6 C1 178.3(4) . . . . ? C4 C5 C6 C1 -1.1(7) . . . . ? C2 C1 C6 C5 -0.5(6) . . . . ? I1 C1 C6 C5 179.3(3) . . . . ? C14 C9 C10 C11 0.7(6) . . . . ? C8 C9 C10 C11 -179.2(4) . . . . ? C9 C10 C11 C12 0.2(6) . . . . ? C15 O1 C12 C13 173.6(4) . . . . ? C15 O1 C12 C11 -6.0(6) . . . . ? C10 C11 C12 O1 178.4(4) . . . . ? C10 C11 C12 C13 -1.1(6) . . . . ? O1 C12 C13 C14 -178.4(4) . . . . ? C11 C12 C13 C14 1.2(6) . . . . ? C12 C13 C14 C9 -0.3(6) . . . . ? C10 C9 C14 C13 -0.7(6) . . . . ? C8 C9 C14 C13 179.2(4) . . . . ?