#------------------------------------------------------------------------------ #$Date: 2022-01-26 14:50:01 +0200 (Wed, 26 Jan 2022) $ #$Revision: 272250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566144.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_1566144 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 'C14 H10 Cl2 O2' _chemical_formula_sum 'C14 H10 Cl2 O2' _chemical_formula_weight 281.12 _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _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 _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.017(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.7651(5) _cell_length_b 21.4851(14) _cell_length_c 7.2877(4) _cell_measurement_reflns_used 2318 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.3630 _cell_measurement_theta_min 3.8190 _cell_volume 1212.85(13) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution sir2004 _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.1856 _diffrn_detector_type Ruby _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'four-circle diffractometer' _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 0.0192 _diffrn_reflns_av_sigmaI/netI 0.0246 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 5071 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 3.38 _exptl_absorpt_coefficient_mu 0.524 _exptl_absorpt_correction_T_max 0.9256 _exptl_absorpt_correction_T_min 0.8587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.540 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.719 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.121 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2137 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.121 _refine_ls_R_factor_all 0.0683 _refine_ls_R_factor_gt 0.0624 _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^)+(0.0579P)^2^+1.7668P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1528 _refine_ls_wR_factor_ref 0.1570 _reflns_number_gt 1918 _reflns_number_total 2137 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL bn_BSF499 in P2(1)/c CELL 0.71073 7.7651 21.4851 7.2877 90.000 94.017 90.000 ZERR 4.00 0.0005 0.0014 0.0004 0.000 0.006 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H O CL UNIT 56 40 8 8 MERG 2 shel 99 0.84 FMAP 2 PLAN 10 SIZE 0.15 0.23 0.30 ACTA 50.00 BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.057900 1.766800 FVAR 6.30087 CL1 4 0.671710 0.005486 0.192373 11.00000 0.06719 0.06462 = 0.06712 -0.02187 0.00629 0.01019 CL2 4 0.109124 0.114604 0.061360 11.00000 0.06217 0.07659 = 0.06270 -0.01187 -0.02778 -0.00284 C1 1 0.679874 0.040270 0.408365 11.00000 0.03255 0.04354 = 0.05280 -0.00033 0.00415 -0.00379 C2 1 0.787903 0.014331 0.547402 11.00000 0.03709 0.04518 = 0.07634 0.01120 0.00269 0.00273 AFIX 43 H2 2 0.849697 -0.021705 0.525855 11.00000 -1.20000 AFIX 0 C3 1 0.802905 0.042300 0.717241 11.00000 0.04318 0.06209 = 0.05981 0.01762 -0.00894 0.00139 AFIX 43 H3 2 0.875643 0.025145 0.810703 11.00000 -1.20000 AFIX 0 C4 1 0.711659 0.095261 0.750241 11.00000 0.04825 0.06310 = 0.04485 0.00621 -0.01051 0.00028 AFIX 43 H4 2 0.724532 0.114483 0.864720 11.00000 -1.20000 AFIX 0 C5 1 0.599807 0.120147 0.612024 11.00000 0.04188 0.04789 = 0.03956 0.00032 -0.00600 0.00078 C6 1 0.503858 0.179897 0.635390 11.00000 0.06767 0.06880 = 0.04534 -0.01721 -0.01724 0.01793 AFIX 13 H6 2 0.562343 0.211609 0.565741 11.00000 -1.20000 AFIX 0 C7 1 0.318115 0.174918 0.546533 11.00000 0.05314 0.04363 = 0.04145 -0.00137 -0.00227 0.00740 C8 1 0.177453 0.199236 0.625629 11.00000 0.06702 0.05263 = 0.05018 0.00054 0.01023 0.00842 AFIX 43 H8 2 0.191025 0.217765 0.741067 11.00000 -1.20000 AFIX 0 C9 1 0.015256 0.196193 0.533580 11.00000 0.05480 0.06325 = 0.07558 0.00974 0.02278 0.00747 AFIX 43 H9 2 -0.080117 0.212116 0.588146 11.00000 -1.20000 AFIX 0 C10 1 -0.004778 0.169645 0.361607 11.00000 0.03957 0.05727 = 0.07871 0.01329 -0.00093 -0.00532 AFIX 43 H10 2 -0.113319 0.167842 0.299217 11.00000 -1.20000 AFIX 0 C11 1 0.136776 0.145796 0.282604 11.00000 0.04329 0.04237 = 0.05343 0.00378 -0.00805 -0.00688 C12 1 0.301523 0.146589 0.372494 11.00000 0.04310 0.03628 = 0.04103 0.00212 -0.00429 0.00065 C13 1 0.458956 0.121010 0.291002 11.00000 0.04512 0.04132 = 0.03919 -0.00734 -0.00852 0.00112 C14 1 0.581073 0.092450 0.438574 11.00000 0.03523 0.03713 = 0.03839 0.00135 -0.00172 -0.00138 O1 3 0.549457 0.170035 0.201581 11.00000 0.05819 0.05522 = 0.03898 0.00390 -0.00343 -0.00182 AFIX 83 H1O 2 0.611141 0.189024 0.278489 11.00000 -1.30000 AFIX 0 O2 3 0.509686 0.200761 0.818201 11.00000 0.11096 0.09319 = 0.03973 -0.01304 -0.01308 0.02449 AFIX 83 H2O 2 0.458824 0.175920 0.880544 11.00000 -1.30000 AFIX 1 H13 2 0.435299 0.091715 0.202914 11.00000 0.04077 HKLF 4 REM bn_BSF499 in P2(1)/c REM R1 = 0.0624 for 1918 Fo > 4sig(Fo) and 0.0683 for all 2137 data REM 163 parameters refined using 0 restraints END WGHT 0.0524 1.6942 REM Highest difference peak 0.719, deepest hole -0.472, 1-sigma level 0.057 Q1 1 0.4234 0.1561 0.8676 11.00000 0.05 0.72 Q2 1 0.4379 0.1503 0.7079 11.00000 0.05 0.54 Q3 1 0.5114 0.1713 0.0818 11.00000 0.05 0.44 Q4 1 0.5137 0.2552 0.8019 11.00000 0.05 0.29 Q5 1 0.5269 0.1028 0.3830 11.00000 0.05 0.21 Q6 1 0.6259 0.0676 0.4026 11.00000 0.05 0.17 Q7 1 0.6703 0.0496 0.1766 11.00000 0.05 0.16 Q8 1 0.3063 0.1704 0.4335 11.00000 0.05 0.16 Q9 1 0.5416 0.0711 0.4689 11.00000 0.05 0.16 Q10 1 0.2424 0.1625 0.6031 11.00000 0.05 0.16 ; _cod_data_source_file Tetrahedron-2020-76-131299.cif _cod_data_source_block 8 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1566144 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_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 Cl1 Cl 0.67171(15) 0.00549(5) 0.19237(16) 0.0662(4) Uani 1 1 d . . . Cl2 Cl 0.10912(14) 0.11460(6) 0.06136(15) 0.0687(4) Uani 1 1 d . . . C1 C 0.6799(4) 0.04027(17) 0.4084(5) 0.0429(8) Uani 1 1 d . . . C2 C 0.7879(5) 0.01433(18) 0.5474(6) 0.0529(10) Uani 1 1 d . . . H2 H 0.8497 -0.0217 0.5259 0.064 Uiso 1 1 calc R . . C3 C 0.8029(5) 0.0423(2) 0.7172(6) 0.0556(10) Uani 1 1 d . . . H3 H 0.8756 0.0251 0.8107 0.067 Uiso 1 1 calc R . . C4 C 0.7117(5) 0.09526(19) 0.7502(5) 0.0527(10) Uani 1 1 d . . . H4 H 0.7245 0.1145 0.8647 0.063 Uiso 1 1 calc R . . C5 C 0.5998(5) 0.12015(17) 0.6120(5) 0.0435(8) Uani 1 1 d . . . C6 C 0.5039(6) 0.1799(2) 0.6354(5) 0.0616(12) Uani 1 1 d . . . H6 H 0.5623 0.2116 0.5657 0.074 Uiso 1 1 calc R . . C7 C 0.3181(5) 0.17492(17) 0.5465(5) 0.0463(9) Uani 1 1 d . . . C8 C 0.1775(6) 0.19924(19) 0.6256(6) 0.0563(10) Uani 1 1 d . . . H8 H 0.1910 0.2178 0.7411 0.068 Uiso 1 1 calc R . . C9 C 0.0153(6) 0.1962(2) 0.5336(6) 0.0637(11) Uani 1 1 d . . . H9 H -0.0801 0.2121 0.5881 0.076 Uiso 1 1 calc R . . C10 C -0.0048(5) 0.16965(19) 0.3616(6) 0.0588(11) Uani 1 1 d . . . H10 H -0.1133 0.1678 0.2992 0.071 Uiso 1 1 calc R . . C11 C 0.1368(5) 0.14580(17) 0.2826(5) 0.0469(9) Uani 1 1 d . . . C12 C 0.3015(5) 0.14659(16) 0.3725(5) 0.0405(8) Uani 1 1 d . . . C13 C 0.4590(5) 0.12101(16) 0.2910(5) 0.0424(8) Uani 1 1 d . . . C14 C 0.5811(4) 0.09245(15) 0.4386(4) 0.0371(7) Uani 1 1 d . . . O1 O 0.5495(3) 0.17003(12) 0.2016(3) 0.0511(7) Uani 1 1 d . . . H1O H 0.6111 0.1890 0.2785 0.066 Uiso 1 1 calc R . . O2 O 0.5097(5) 0.20076(17) 0.8182(4) 0.0822(11) Uani 1 1 d . . . H2O H 0.4588 0.1759 0.8805 0.107 Uiso 1 1 calc R . . H13 H 0.4353 0.0917 0.2029 0.041 Uiso 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 Cl1 0.0672(7) 0.0646(7) 0.0671(7) -0.0219(5) 0.0063(5) 0.0102(5) Cl2 0.0622(7) 0.0766(8) 0.0627(7) -0.0119(5) -0.0278(5) -0.0028(5) C1 0.0325(17) 0.0435(19) 0.053(2) -0.0003(16) 0.0042(15) -0.0038(15) C2 0.0371(19) 0.045(2) 0.076(3) 0.011(2) 0.0027(18) 0.0027(16) C3 0.043(2) 0.062(2) 0.060(2) 0.018(2) -0.0089(18) 0.0014(19) C4 0.048(2) 0.063(2) 0.045(2) 0.0062(18) -0.0105(16) 0.0003(19) C5 0.0419(19) 0.048(2) 0.0396(18) 0.0003(15) -0.0060(15) 0.0008(16) C6 0.068(3) 0.069(3) 0.045(2) -0.0172(19) -0.0172(19) 0.018(2) C7 0.053(2) 0.044(2) 0.0415(19) -0.0014(15) -0.0023(16) 0.0074(17) C8 0.067(3) 0.053(2) 0.050(2) 0.0005(18) 0.0102(19) 0.008(2) C9 0.055(3) 0.063(3) 0.076(3) 0.010(2) 0.023(2) 0.007(2) C10 0.040(2) 0.057(2) 0.079(3) 0.013(2) -0.001(2) -0.0053(18) C11 0.043(2) 0.0424(19) 0.053(2) 0.0038(16) -0.0080(16) -0.0069(16) C12 0.0431(19) 0.0363(17) 0.0410(18) 0.0021(14) -0.0043(14) 0.0006(15) C13 0.045(2) 0.0413(18) 0.0392(18) -0.0073(15) -0.0085(15) 0.0011(16) C14 0.0352(17) 0.0371(17) 0.0384(17) 0.0014(14) -0.0017(14) -0.0014(14) O1 0.0582(16) 0.0552(15) 0.0390(13) 0.0039(11) -0.0034(11) -0.0018(13) O2 0.111(3) 0.093(2) 0.0397(15) -0.0130(15) -0.0131(16) 0.024(2) 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' Cl Cl 0.1484 0.1585 '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 C14 C1 C2 121.5(3) . . C14 C1 Cl1 120.4(3) . . C2 C1 Cl1 118.1(3) . . C3 C2 C1 119.4(4) . . C3 C2 H2 120.3 . . C1 C2 H2 120.3 . . C4 C3 C2 120.6(4) . . C4 C3 H3 119.7 . . C2 C3 H3 119.7 . . C3 C4 C5 119.8(4) . . C3 C4 H4 120.1 . . C5 C4 H4 120.1 . . C4 C5 C14 120.8(3) . . C4 C5 C6 122.5(3) . . C14 C5 C6 116.5(3) . . O2 C6 C5 113.4(3) . . O2 C6 C7 112.8(4) . . C5 C6 C7 110.5(3) . . O2 C6 H6 106.5 . . C5 C6 H6 106.5 . . C7 C6 H6 106.5 . . C8 C7 C12 121.2(4) . . C8 C7 C6 123.0(3) . . C12 C7 C6 115.7(3) . . C7 C8 C9 120.1(4) . . C7 C8 H8 120.0 . . C9 C8 H8 120.0 . . C10 C9 C8 120.1(4) . . C10 C9 H9 120.0 . . C8 C9 H9 120.0 . . C11 C10 C9 119.6(4) . . C11 C10 H10 120.2 . . C9 C10 H10 120.2 . . C10 C11 C12 122.1(4) . . C10 C11 Cl2 118.7(3) . . C12 C11 Cl2 119.2(3) . . C11 C12 C7 116.9(3) . . C11 C12 C13 123.7(3) . . C7 C12 C13 119.4(3) . . O1 C13 C12 110.3(3) . . O1 C13 C14 108.4(3) . . C12 C13 C14 110.8(3) . . O1 C13 H13 105.5 . . C12 C13 H13 113.8 . . C14 C13 H13 107.9 . . C1 C14 C5 117.7(3) . . C1 C14 C13 122.8(3) . . C5 C14 C13 119.4(3) . . C13 O1 H1O 109.5 . . C6 O2 H2O 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl1 C1 1.740(4) . Cl2 C11 1.745(4) . C1 C14 1.385(5) . C1 C2 1.386(5) . C2 C3 1.373(6) . C2 H2 0.9300 . C3 C4 1.371(6) . C3 H3 0.9300 . C4 C5 1.390(5) . C4 H4 0.9300 . C5 C14 1.395(5) . C5 C6 1.500(5) . C6 O2 1.403(5) . C6 C7 1.543(6) . C6 H6 0.9800 . C7 C8 1.373(5) . C7 C12 1.405(5) . C8 C9 1.386(6) . C8 H8 0.9300 . C9 C10 1.376(6) . C9 H9 0.9300 . C10 C11 1.375(6) . C10 H10 0.9300 . C11 C12 1.396(5) . C12 C13 1.500(5) . C13 O1 1.446(4) . C13 C14 1.513(5) . C13 H13 0.9086 . O1 H1O 0.8200 . O2 H2O 0.8200 . 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 C14 C1 C2 C3 -2.6(6) . . . . Cl1 C1 C2 C3 177.2(3) . . . . C1 C2 C3 C4 0.3(6) . . . . C2 C3 C4 C5 1.5(6) . . . . C3 C4 C5 C14 -1.0(6) . . . . C3 C4 C5 C6 -176.4(4) . . . . C4 C5 C6 O2 -12.4(6) . . . . C14 C5 C6 O2 172.0(4) . . . . C4 C5 C6 C7 -140.3(4) . . . . C14 C5 C6 C7 44.2(5) . . . . O2 C6 C7 C8 11.4(6) . . . . C5 C6 C7 C8 139.6(4) . . . . O2 C6 C7 C12 -171.9(3) . . . . C5 C6 C7 C12 -43.7(5) . . . . C12 C7 C8 C9 -0.1(6) . . . . C6 C7 C8 C9 176.4(4) . . . . C7 C8 C9 C10 -1.0(6) . . . . C8 C9 C10 C11 0.5(6) . . . . C9 C10 C11 C12 1.1(6) . . . . C9 C10 C11 Cl2 -178.0(3) . . . . C10 C11 C12 C7 -2.1(5) . . . . Cl2 C11 C12 C7 177.0(3) . . . . C10 C11 C12 C13 180.0(3) . . . . Cl2 C11 C12 C13 -1.0(5) . . . . C8 C7 C12 C11 1.6(5) . . . . C6 C7 C12 C11 -175.2(3) . . . . C8 C7 C12 C13 179.6(3) . . . . C6 C7 C12 C13 2.9(5) . . . . C11 C12 C13 O1 94.6(4) . . . . C7 C12 C13 O1 -83.3(4) . . . . C11 C12 C13 C14 -145.4(3) . . . . C7 C12 C13 C14 36.7(4) . . . . C2 C1 C14 C5 3.0(5) . . . . Cl1 C1 C14 C5 -176.8(3) . . . . C2 C1 C14 C13 -178.6(3) . . . . Cl1 C1 C14 C13 1.6(5) . . . . C4 C5 C14 C1 -1.2(5) . . . . C6 C5 C14 C1 174.5(3) . . . . C4 C5 C14 C13 -179.6(3) . . . . C6 C5 C14 C13 -4.0(5) . . . . O1 C13 C14 C1 -93.9(4) . . . . C12 C13 C14 C1 144.9(3) . . . . O1 C13 C14 C5 84.4(4) . . . . C12 C13 C14 C5 -36.7(4) . . . .