#------------------------------------------------------------------------------ #$Date: 2022-01-26 14:50:01 +0200 (Wed, 26 Jan 2022) $ #$Revision: 272250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566146.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_1566146 loop_ _publ_author_name 'Forensi, Silvia' 'Stopin, Antoine' 'de Leo, Federica' 'Wouters, Johan' 'Bonifazi, Davide' _publ_section_title ; 1,8,10-Trisubstituted anthracenyl hydrocarbons: Towards versatile scaffolds for multiple-H-bonded recognition arrays ; _journal_issue 51 _journal_name_full Tetrahedron _journal_page_first 131299 _journal_paper_doi 10.1016/j.tet.2020.131299 _journal_volume 76 _journal_year 2020 _chemical_formula_moiety 'C11 H15 B O3' _chemical_formula_sum 'C11 H15 B O3' _chemical_formula_weight 206.04 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 93.205(4) _cell_angle_beta 94.213(4) _cell_angle_gamma 109.868(5) _cell_formula_units_Z 2 _cell_length_a 6.9873(4) _cell_length_b 7.9428(4) _cell_length_c 11.0964(6) _cell_measurement_reflns_used 2969 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 32.6658 _cell_measurement_theta_min 3.1613 _cell_volume 575.46(6) _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 10.3712 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra' _diffrn_measurement_method '\w scans' _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 0.0148 _diffrn_reflns_av_sigmaI/netI 0.0180 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 4333 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 3.17 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.9835 _exptl_absorpt_correction_T_min 0.9795 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.189 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 220 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.265 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 136 _refine_ls_number_reflns 2033 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0554 _refine_ls_R_factor_gt 0.0498 _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^)+(0.0912P)^2^+0.0955P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1523 _refine_ls_wR_factor_ref 0.1586 _reflns_number_gt 1768 _reflns_number_total 2033 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL bn_BSF093bis in P-1 CELL 0.71073 6.9873 7.9428 11.0964 93.205 94.213 109.868 ZERR 2.00 0.0004 0.0004 0.0006 0.004 0.004 0.005 LATT 1 SFAC C H B O UNIT 22 30 2 6 MERG 2 SHEL 99 0.84 FMAP 2 PLAN 10 SIZE 0.20 0.20 0.25 BOND $H CONF ACTA 50 L.S. 10 TEMP 20.00 WGHT 0.091200 0.095500 FVAR 12.76803 O1 4 -0.298062 0.625777 0.395860 11.00000 0.06458 0.06726 = 0.08545 0.02714 0.02936 0.03798 AFIX 3 H1A 2 -0.406672 0.633847 0.430359 11.00000 -1.50000 AFIX 0 O2 4 -0.396018 0.342560 0.469446 11.00000 0.05990 0.06165 = 0.08344 0.02285 0.02653 0.02867 AFIX 3 H2A 2 -0.380688 0.244090 0.459136 11.00000 -1.50000 AFIX 0 O3 4 -0.226958 0.096698 0.471161 11.00000 0.08122 0.05955 = 0.07890 0.02450 0.02404 0.03037 C1 1 -0.088815 0.440216 0.336865 11.00000 0.04692 0.05014 = 0.04481 0.00447 0.00193 0.01866 C2 1 -0.015047 0.295069 0.338273 11.00000 0.05645 0.05281 = 0.04873 0.00581 0.00412 0.02395 C3 1 0.149647 0.299901 0.273723 11.00000 0.07254 0.06506 = 0.06613 0.00916 0.01667 0.03958 AFIX 43 H3 2 0.197888 0.204310 0.275196 11.00000 -1.20000 AFIX 0 C4 1 0.243782 0.441820 0.207592 11.00000 0.06360 0.07141 = 0.06227 0.00647 0.02105 0.02987 AFIX 43 H4 2 0.353504 0.440212 0.165482 11.00000 -1.20000 AFIX 0 C5 1 0.176780 0.586285 0.203264 11.00000 0.05556 0.05361 = 0.04678 0.00083 0.00787 0.01463 C6 1 0.011838 0.580420 0.269222 11.00000 0.05458 0.04974 = 0.05161 0.00663 0.00820 0.02135 AFIX 43 H6 2 -0.033960 0.677450 0.267755 11.00000 -1.20000 AFIX 0 C7 1 -0.089661 0.135808 0.406094 11.00000 0.07951 0.05975 = 0.06649 0.01671 0.01515 0.03800 AFIX 43 H7 2 -0.022102 0.053735 0.397909 11.00000 -1.20000 AFIX 0 C8 1 0.281877 0.750097 0.135705 11.00000 0.07022 0.06084 = 0.05871 0.00869 0.01917 0.01462 C9 1 0.403421 0.706229 0.038731 11.00000 0.24451 0.09323 = 0.17208 0.04438 0.15969 0.05351 AFIX 33 H9A 2 0.313431 0.613818 -0.019208 11.00000 -1.50000 H9B 2 0.506324 0.665095 0.075491 11.00000 -1.50000 H9C 2 0.467545 0.811970 -0.001554 11.00000 -1.50000 AFIX 0 C10 1 0.418698 0.896569 0.228855 11.00000 0.10434 0.06984 = 0.09813 0.01779 -0.00630 -0.00254 AFIX 33 H10A 2 0.338099 0.922218 0.288968 11.00000 -1.50000 H10B 2 0.482823 1.003188 0.189432 11.00000 -1.50000 H10C 2 0.521778 0.857013 0.267126 11.00000 -1.50000 AFIX 0 C11 1 0.125138 0.820438 0.072739 11.00000 0.10481 0.12210 = 0.11137 0.06844 -0.00021 0.01233 AFIX 33 H11A 2 0.037168 0.729767 0.013013 11.00000 -1.50000 H11B 2 0.195164 0.926173 0.033988 11.00000 -1.50000 H11C 2 0.044861 0.849455 0.131758 11.00000 -1.50000 AFIX 0 B1 3 -0.270792 0.466699 0.405170 11.00000 0.04530 0.05589 = 0.05373 0.00980 0.00441 0.02106 HKLF 4 REM bn_BSF093bis in P-1 REM R1 = 0.0498 for 1768 Fo > 4sig(Fo) and 0.0554 for all 2033 data REM 136 parameters refined using 0 restraints END WGHT 0.0904 0.0959 REM Highest difference peak 0.265, deepest hole -0.163, 1-sigma level 0.037 Q1 1 0.5381 0.7601 0.1401 11.00000 0.05 0.27 Q2 1 -0.1444 0.4552 0.3840 11.00000 0.05 0.16 Q3 1 0.2251 0.7039 0.0170 11.00000 0.05 0.14 Q4 1 0.4181 0.6157 0.0141 11.00000 0.05 0.14 Q5 1 -0.2082 0.4152 0.3419 11.00000 0.05 0.13 Q6 1 0.2518 0.9261 0.1904 11.00000 0.05 0.13 Q7 1 -0.3237 0.2716 0.5052 11.00000 0.05 0.12 Q8 1 -0.3698 0.5451 0.3287 11.00000 0.05 0.11 Q9 1 0.4079 0.8065 -0.0251 11.00000 0.05 0.10 Q10 1 -0.0294 0.3901 0.3677 11.00000 0.05 0.10 ; _cod_data_source_file Tetrahedron-2020-76-131299.cif _cod_data_source_block 10 _cod_original_cell_volume 575.46(5) _cod_database_code 1566146 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.29806(19) 0.62578(17) 0.39586(13) 0.0665(4) Uani 1 1 d . . . H1A H -0.4067 0.6338 0.4304 0.100 Uiso 1 1 d R . . O2 O -0.39602(18) 0.34256(17) 0.46945(12) 0.0647(4) Uani 1 1 d . . . H2A H -0.3807 0.2441 0.4591 0.097 Uiso 1 1 d R . . O3 O -0.2270(2) 0.09670(17) 0.47116(13) 0.0701(4) Uani 1 1 d . . . C1 C -0.0888(2) 0.4402(2) 0.33686(14) 0.0469(4) Uani 1 1 d . . . C2 C -0.0150(3) 0.2951(2) 0.33827(15) 0.0514(4) Uani 1 1 d . . . C3 C 0.1496(3) 0.2999(3) 0.27372(17) 0.0632(5) Uani 1 1 d . . . H3 H 0.1979 0.2043 0.2752 0.076 Uiso 1 1 calc R . . C4 C 0.2438(3) 0.4418(3) 0.20759(17) 0.0633(5) Uani 1 1 d . . . H4 H 0.3535 0.4402 0.1655 0.076 Uiso 1 1 calc R . . C5 C 0.1768(3) 0.5863(2) 0.20326(15) 0.0531(4) Uani 1 1 d . . . C6 C 0.0118(2) 0.5804(2) 0.26922(15) 0.0509(4) Uani 1 1 d . . . H6 H -0.0340 0.6774 0.2678 0.061 Uiso 1 1 calc R . . C7 C -0.0897(3) 0.1358(3) 0.40609(18) 0.0641(5) Uani 1 1 d . . . H7 H -0.0221 0.0537 0.3979 0.077 Uiso 1 1 calc R . . C8 C 0.2819(3) 0.7501(3) 0.13571(17) 0.0645(5) Uani 1 1 d . . . C9 C 0.4034(7) 0.7062(4) 0.0387(4) 0.163(2) Uani 1 1 d . . . H9A H 0.3134 0.6138 -0.0192 0.244 Uiso 1 1 calc R . . H9B H 0.5063 0.6651 0.0755 0.244 Uiso 1 1 calc R . . H9C H 0.4675 0.8120 -0.0016 0.244 Uiso 1 1 calc R . . C10 C 0.4187(4) 0.8966(3) 0.2289(3) 0.0996(8) Uani 1 1 d . . . H10A H 0.3381 0.9222 0.2890 0.149 Uiso 1 1 calc R . . H10B H 0.4828 1.0032 0.1894 0.149 Uiso 1 1 calc R . . H10C H 0.5218 0.8570 0.2671 0.149 Uiso 1 1 calc R . . C11 C 0.1251(5) 0.8204(4) 0.0727(3) 0.1179(11) Uani 1 1 d . . . H11A H 0.0372 0.7298 0.0130 0.177 Uiso 1 1 calc R . . H11B H 0.1952 0.9262 0.0340 0.177 Uiso 1 1 calc R . . H11C H 0.0449 0.8495 0.1318 0.177 Uiso 1 1 calc R . . B1 B -0.2708(3) 0.4667(3) 0.40517(17) 0.0505(5) Uani 1 1 d . . . 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 0.0646(8) 0.0673(8) 0.0854(9) 0.0271(7) 0.0294(7) 0.0380(6) O2 0.0599(7) 0.0617(8) 0.0834(9) 0.0229(6) 0.0265(6) 0.0287(6) O3 0.0812(9) 0.0595(8) 0.0789(9) 0.0245(7) 0.0240(7) 0.0304(7) C1 0.0469(8) 0.0501(9) 0.0448(8) 0.0045(6) 0.0019(6) 0.0187(7) C2 0.0564(9) 0.0528(9) 0.0487(9) 0.0058(7) 0.0041(7) 0.0240(7) C3 0.0725(11) 0.0651(11) 0.0661(11) 0.0092(9) 0.0167(9) 0.0396(9) C4 0.0636(11) 0.0714(12) 0.0623(11) 0.0065(9) 0.0210(9) 0.0299(9) C5 0.0556(9) 0.0536(9) 0.0468(9) 0.0008(7) 0.0079(7) 0.0146(7) C6 0.0546(9) 0.0497(9) 0.0516(9) 0.0066(7) 0.0082(7) 0.0214(7) C7 0.0795(12) 0.0597(11) 0.0665(11) 0.0167(9) 0.0152(10) 0.0380(9) C8 0.0702(11) 0.0608(11) 0.0587(11) 0.0087(8) 0.0192(9) 0.0146(9) C9 0.245(5) 0.093(2) 0.172(3) 0.044(2) 0.160(4) 0.054(2) C10 0.1043(18) 0.0698(14) 0.0981(18) 0.0178(12) -0.0063(14) -0.0025(13) C11 0.105(2) 0.122(2) 0.111(2) 0.0684(19) -0.0002(16) 0.0123(17) B1 0.0453(9) 0.0559(10) 0.0537(10) 0.0098(8) 0.0044(8) 0.0211(8) 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' B B 0.0013 0.0007 '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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 B1 O1 H1A 113.9 . . B1 O2 H2A 111.5 . . C6 C1 C2 116.38(14) . . C6 C1 B1 115.23(14) . . C2 C1 B1 128.38(15) . . C3 C2 C1 119.28(15) . . C3 C2 C7 113.98(15) . . C1 C2 C7 126.70(15) . . C4 C3 C2 122.14(16) . . C4 C3 H3 118.9 . . C2 C3 H3 118.9 . . C3 C4 C5 120.66(16) . . C3 C4 H4 119.7 . . C5 C4 H4 119.7 . . C4 C5 C6 116.67(16) . . C4 C5 C8 122.52(16) . . C6 C5 C8 120.74(16) . . C1 C6 C5 124.88(15) . . C1 C6 H6 117.6 . . C5 C6 H6 117.6 . . O3 C7 C2 128.87(16) . . O3 C7 H7 115.6 . . C2 C7 H7 115.6 . . C9 C8 C10 111.1(3) . . C9 C8 C5 111.73(18) . . C10 C8 C5 107.54(16) . . C9 C8 C11 107.2(3) . . C10 C8 C11 108.1(2) . . C5 C8 C11 111.11(16) . . C8 C9 H9A 109.5 . . C8 C9 H9B 109.5 . . H9A C9 H9B 109.5 . . C8 C9 H9C 109.5 . . H9A C9 H9C 109.5 . . H9B C9 H9C 109.5 . . C8 C10 H10A 109.5 . . C8 C10 H10B 109.5 . . H10A C10 H10B 109.5 . . C8 C10 H10C 109.5 . . H10A C10 H10C 109.5 . . H10B C10 H10C 109.5 . . C8 C11 H11A 109.5 . . C8 C11 H11B 109.5 . . H11A C11 H11B 109.5 . . C8 C11 H11C 109.5 . . H11A C11 H11C 109.5 . . H11B C11 H11C 109.5 . . O1 B1 O2 119.33(15) . . O1 B1 C1 115.87(15) . . O2 B1 C1 124.80(15) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 O1 B1 1.349(2) . O1 H1A 0.8942 . O2 B1 1.353(2) . O2 H2A 0.8277 . O3 C7 1.209(2) . C1 C6 1.392(2) . C1 C2 1.414(2) . C1 B1 1.594(2) . C2 C3 1.390(2) . C2 C7 1.468(2) . C3 C4 1.379(3) . C3 H3 0.9300 . C4 C5 1.381(3) . C4 H4 0.9300 . C5 C6 1.399(2) . C5 C8 1.528(2) . C6 H6 0.9300 . C7 H7 0.9300 . C8 C9 1.515(3) . C8 C10 1.517(3) . C8 C11 1.532(4) . C9 H9A 0.9600 . C9 H9B 0.9600 . C9 H9C 0.9600 . C10 H10A 0.9600 . C10 H10B 0.9600 . C10 H10C 0.9600 . C11 H11A 0.9600 . C11 H11B 0.9600 . C11 H11C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C6 C1 C2 C3 0.0(2) . . . . B1 C1 C2 C3 -178.68(16) . . . . C6 C1 C2 C7 177.50(16) . . . . B1 C1 C2 C7 -1.2(3) . . . . C1 C2 C3 C4 -0.2(3) . . . . C7 C2 C3 C4 -178.06(17) . . . . C2 C3 C4 C5 0.1(3) . . . . C3 C4 C5 C6 0.3(3) . . . . C3 C4 C5 C8 177.33(17) . . . . C2 C1 C6 C5 0.5(3) . . . . B1 C1 C6 C5 179.31(15) . . . . C4 C5 C6 C1 -0.6(3) . . . . C8 C5 C6 C1 -177.68(16) . . . . C3 C2 C7 O3 178.7(2) . . . . C1 C2 C7 O3 1.1(3) . . . . C4 C5 C8 C9 22.4(3) . . . . C6 C5 C8 C9 -160.8(3) . . . . C4 C5 C8 C10 -99.8(2) . . . . C6 C5 C8 C10 77.1(2) . . . . C4 C5 C8 C11 142.1(2) . . . . C6 C5 C8 C11 -41.1(3) . . . . C6 C1 B1 O1 -4.0(2) . . . . C2 C1 B1 O1 174.72(16) . . . . C6 C1 B1 O2 175.75(16) . . . . C2 C1 B1 O2 -5.6(3) . . . .