#------------------------------------------------------------------------------ #$Date: 2022-01-26 14:50:01 +0200 (Wed, 26 Jan 2022) $ #$Revision: 272250 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/61/1566145.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_1566145 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 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 93.774(7) _cell_angle_beta 103.555(8) _cell_angle_gamma 92.372(7) _cell_formula_units_Z 2 _cell_length_a 7.2545(6) _cell_length_b 7.8698(6) _cell_length_c 10.9539(10) _cell_measurement_reflns_used 2190 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 28.8230 _cell_measurement_theta_min 3.0450 _cell_volume 605.59(9) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution shelxs86 _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 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 0.0330 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_max 7 _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 -10 _diffrn_reflns_number 4353 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.89 _exptl_absorpt_coefficient_mu 0.525 _exptl_absorpt_correction_T_max 0.9115 _exptl_absorpt_correction_T_min 0.7944 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET) (compiled May 22 2014,16:03:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.542 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.298 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 179 _refine_ls_number_reflns 2136 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.110 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0511 _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^)+(0.0491P)^2^+0.3495P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1175 _refine_ls_wR_factor_ref 0.1239 _reflns_number_gt 1826 _reflns_number_total 2136 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL bn_BSF587-3F in P-1 CELL 0.71073 7.2545 7.8698 10.9539 93.774 103.555 92.372 ZERR 2.00 0.0006 0.0006 0.0010 0.007 0.008 0.007 LATT 1 SFAC C H O CL UNIT 28 20 4 4 MERG 2 SHEL 99 0.84 DFIX 0.82 0.001 O1 H1o O2 H2o FMAP 2 PLAN 10 SIZE 0.18 0.30 0.46 ACTA 50.00 HTAB 2.00000 BOND $H CONF L.S. 10 TEMP 20.00 WGHT 0.049100 0.349500 FVAR 10.63300 C1 1 0.384183 0.177700 0.788199 11.00000 0.05300 0.03973 = 0.03619 -0.00399 0.02025 -0.00958 C2 1 0.474260 0.034785 0.832925 11.00000 0.08378 0.02683 = 0.05547 0.00157 0.03171 -0.00462 AFIX 43 H2 2 0.405332 -0.068921 0.827225 11.00000 -1.20000 AFIX 0 C3 1 0.666704 0.047217 0.885938 11.00000 0.08509 0.03453 = 0.06335 0.01294 0.03155 0.01866 AFIX 43 H3 2 0.727715 -0.048705 0.915775 11.00000 -1.20000 AFIX 0 C4 1 0.769863 0.201054 0.895154 11.00000 0.05980 0.04203 = 0.04833 0.00756 0.02002 0.01146 AFIX 43 H4 2 0.899414 0.209392 0.932206 11.00000 -1.20000 AFIX 0 C5 1 0.781632 0.515311 0.861389 11.00000 0.03142 0.04095 = 0.04075 0.00401 0.00993 0.00038 C6 1 0.678232 0.343229 0.848538 11.00000 0.04382 0.03350 = 0.03328 0.00298 0.01508 0.00269 C7 1 0.717361 0.611600 0.746483 11.00000 0.04089 0.03009 = 0.03773 -0.00039 0.01441 -0.00235 C8 1 0.845804 0.710933 0.700500 11.00000 0.05126 0.04319 = 0.04539 0.00036 0.02021 -0.00484 AFIX 43 H8 2 0.974740 0.717003 0.739254 11.00000 -1.20000 AFIX 0 C9 1 0.778069 0.800032 0.596455 11.00000 0.06639 0.04216 = 0.05059 0.00695 0.02757 -0.00916 AFIX 43 H9 2 0.862560 0.866609 0.565018 11.00000 -1.20000 AFIX 0 C10 1 0.588036 0.792058 0.538552 11.00000 0.07769 0.03397 = 0.03726 0.00927 0.02409 0.00616 AFIX 43 H10 2 0.544136 0.852149 0.468164 11.00000 -1.20000 AFIX 0 C11 1 0.462390 0.693685 0.585972 11.00000 0.05148 0.03586 = 0.03470 0.00222 0.01256 0.00785 C12 1 0.524005 0.600999 0.690272 11.00000 0.04196 0.02696 = 0.03178 -0.00039 0.01460 0.00366 C13 1 0.391498 0.492678 0.745178 11.00000 0.03314 0.03662 = 0.03384 0.00231 0.00584 0.00054 C14 1 0.483461 0.333865 0.793106 11.00000 0.04239 0.02953 = 0.03048 0.00085 0.01501 -0.00084 O1 3 0.745929 0.618114 0.967246 11.00000 0.05747 0.04027 = 0.03606 -0.00039 0.01220 -0.00677 O2 3 0.340499 0.593271 0.846728 11.00000 0.05412 0.04094 = 0.04515 0.00686 0.02094 0.01212 CL1 4 0.139593 0.158476 0.725355 11.00000 0.05632 0.06638 = 0.06232 -0.00072 0.01470 -0.02669 CL2 4 0.221856 0.692529 0.512851 11.00000 0.05595 0.07347 = 0.05247 0.01800 0.00425 0.01794 H13 2 0.280942 0.466537 0.686572 11.00000 0.03571 H5 2 0.915315 0.509372 0.875639 11.00000 0.04552 H1O 2 0.747672 0.553856 1.023417 11.00000 0.10537 H2O 2 0.433877 0.623538 0.903536 11.00000 0.14599 HKLF 4 REM bn_BSF587-3F in P-1 REM R1 = 0.0511 for 1826 Fo > 4sig(Fo) and 0.0618 for all 2136 data REM 179 parameters refined using 2 restraints END WGHT 0.0464 0.3697 REM Highest difference peak 0.298, deepest hole -0.271, 1-sigma level 0.057 Q1 1 0.1841 0.1364 0.8267 11.00000 0.05 0.30 Q2 1 0.2615 0.6872 0.6168 11.00000 0.05 0.29 Q3 1 0.2343 0.5812 0.5665 11.00000 0.05 0.24 Q4 1 0.1164 0.1719 0.6174 11.00000 0.05 0.24 Q5 1 0.1454 0.2703 0.8159 11.00000 0.05 0.23 Q6 1 0.3245 0.5092 0.8986 11.00000 0.05 0.23 Q7 1 0.4330 0.1349 0.8585 11.00000 0.05 0.22 Q8 1 0.1914 0.7068 0.4199 11.00000 0.05 0.22 Q9 1 0.7229 0.4198 0.8566 11.00000 0.05 0.22 Q10 1 0.4339 0.4050 0.7704 11.00000 0.05 0.21 ; _cod_data_source_file Tetrahedron-2020-76-131299.cif _cod_data_source_block 9 _cod_database_code 1566145 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 C1 C 0.3842(4) 0.1777(4) 0.7882(3) 0.0420(7) Uani 1 1 d . . . C2 C 0.4743(5) 0.0348(4) 0.8329(3) 0.0531(8) Uani 1 1 d . . . H2 H 0.4053 -0.0689 0.8272 0.064 Uiso 1 1 calc R . . C3 C 0.6667(5) 0.0472(4) 0.8859(3) 0.0578(9) Uani 1 1 d . . . H3 H 0.7277 -0.0487 0.9158 0.069 Uiso 1 1 calc R . . C4 C 0.7699(5) 0.2011(4) 0.8952(3) 0.0484(8) Uani 1 1 d . . . H4 H 0.8994 0.2094 0.9322 0.058 Uiso 1 1 calc R . . C5 C 0.7816(4) 0.5153(4) 0.8614(3) 0.0375(6) Uani 1 1 d . . . C6 C 0.6782(4) 0.3432(3) 0.8485(2) 0.0359(6) Uani 1 1 d . . . C7 C 0.7174(4) 0.6116(3) 0.7465(3) 0.0357(6) Uani 1 1 d . . . C8 C 0.8458(4) 0.7109(4) 0.7005(3) 0.0455(7) Uani 1 1 d . . . H8 H 0.9747 0.7170 0.7393 0.055 Uiso 1 1 calc R . . C9 C 0.7781(5) 0.8000(4) 0.5965(3) 0.0510(8) Uani 1 1 d . . . H9 H 0.8626 0.8666 0.5650 0.061 Uiso 1 1 calc R . . C10 C 0.5880(5) 0.7921(4) 0.5386(3) 0.0475(8) Uani 1 1 d . . . H10 H 0.5441 0.8521 0.4682 0.057 Uiso 1 1 calc R . . C11 C 0.4624(4) 0.6937(4) 0.5860(3) 0.0402(7) Uani 1 1 d . . . C12 C 0.5240(4) 0.6010(3) 0.6903(2) 0.0327(6) Uani 1 1 d . . . C13 C 0.3915(4) 0.4927(3) 0.7452(3) 0.0349(6) Uani 1 1 d . . . C14 C 0.4835(4) 0.3339(3) 0.7931(2) 0.0332(6) Uani 1 1 d . . . O1 O 0.7459(3) 0.6181(3) 0.96725(19) 0.0448(5) Uani 1 1 d D . . O2 O 0.3405(3) 0.5933(3) 0.8467(2) 0.0448(5) Uani 1 1 d D . . Cl1 Cl 0.13959(12) 0.15848(12) 0.72536(8) 0.0627(3) Uani 1 1 d . . . Cl2 Cl 0.22186(12) 0.69253(12) 0.51285(8) 0.0611(3) Uani 1 1 d . . . H13 H 0.281(4) 0.467(3) 0.687(3) 0.036(7) Uiso 1 1 d . . . H5 H 0.915(4) 0.509(4) 0.876(3) 0.046(8) Uiso 1 1 d . . . H1O H 0.748(7) 0.554(5) 1.023(3) 0.105(17) Uiso 1 1 d D . . H2O H 0.434(5) 0.624(7) 0.904(4) 0.15(2) Uiso 1 1 d 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 C1 0.0530(17) 0.0397(17) 0.0362(15) -0.0040(12) 0.0202(13) -0.0096(13) C2 0.084(2) 0.0268(15) 0.0555(19) 0.0016(14) 0.0317(18) -0.0046(15) C3 0.085(3) 0.0345(17) 0.063(2) 0.0129(15) 0.0316(19) 0.0187(16) C4 0.0598(19) 0.0420(18) 0.0483(18) 0.0076(14) 0.0200(15) 0.0115(14) C5 0.0314(14) 0.0409(16) 0.0408(15) 0.0040(12) 0.0099(12) 0.0004(11) C6 0.0438(15) 0.0335(15) 0.0333(14) 0.0030(11) 0.0151(12) 0.0027(11) C7 0.0409(14) 0.0301(14) 0.0377(14) -0.0004(11) 0.0144(12) -0.0023(11) C8 0.0513(17) 0.0432(17) 0.0454(17) 0.0004(14) 0.0202(14) -0.0048(13) C9 0.066(2) 0.0422(18) 0.0506(18) 0.0069(14) 0.0276(16) -0.0092(15) C10 0.078(2) 0.0340(16) 0.0373(16) 0.0093(13) 0.0241(16) 0.0062(14) C11 0.0515(17) 0.0359(15) 0.0347(15) 0.0022(12) 0.0126(13) 0.0078(12) C12 0.0420(14) 0.0270(13) 0.0318(14) -0.0004(11) 0.0146(12) 0.0037(11) C13 0.0331(14) 0.0366(15) 0.0338(14) 0.0023(12) 0.0058(12) 0.0005(11) C14 0.0424(14) 0.0295(14) 0.0305(14) 0.0009(11) 0.0150(12) -0.0008(11) O1 0.0575(13) 0.0403(12) 0.0361(11) -0.0004(9) 0.0122(10) -0.0068(9) O2 0.0541(13) 0.0409(12) 0.0452(12) 0.0069(9) 0.0209(11) 0.0121(10) Cl1 0.0563(5) 0.0664(6) 0.0623(5) -0.0007(4) 0.0147(4) -0.0267(4) Cl2 0.0560(5) 0.0735(6) 0.0525(5) 0.0180(4) 0.0043(4) 0.0179(4) 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 C2 C1 C14 121.7(3) . . C2 C1 Cl1 118.3(2) . . C14 C1 Cl1 120.0(2) . . C3 C2 C1 119.5(3) . . C3 C2 H2 120.2 . . C1 C2 H2 120.2 . . C2 C3 C4 120.5(3) . . C2 C3 H3 119.7 . . C4 C3 H3 119.7 . . C3 C4 C6 119.4(3) . . C3 C4 H4 120.3 . . C6 C4 H4 120.3 . . O1 C5 C7 107.2(2) . . O1 C5 C6 110.1(2) . . C7 C5 C6 112.0(2) . . O1 C5 H5 106.9(18) . . C7 C5 H5 107.3(18) . . C6 C5 H5 113.1(18) . . C4 C6 C14 121.3(3) . . C4 C6 C5 121.6(3) . . C14 C6 C5 117.1(2) . . C12 C7 C8 121.6(3) . . C12 C7 C5 117.1(2) . . C8 C7 C5 121.3(3) . . C9 C8 C7 118.8(3) . . C9 C8 H8 120.6 . . C7 C8 H8 120.6 . . C10 C9 C8 121.1(3) . . C10 C9 H9 119.4 . . C8 C9 H9 119.4 . . C9 C10 C11 119.3(3) . . C9 C10 H10 120.3 . . C11 C10 H10 120.3 . . C10 C11 C12 121.7(3) . . C10 C11 Cl2 117.9(2) . . C12 C11 Cl2 120.5(2) . . C7 C12 C11 117.5(2) . . C7 C12 C13 119.2(2) . . C11 C12 C13 123.3(2) . . O2 C13 C14 110.3(2) . . O2 C13 C12 108.7(2) . . C14 C13 C12 111.0(2) . . O2 C13 H13 105.6(18) . . C14 C13 H13 111.3(17) . . C12 C13 H13 109.8(17) . . C1 C14 C6 117.5(2) . . C1 C14 C13 123.6(2) . . C6 C14 C13 118.9(2) . . C5 O1 H1O 106(3) . . C13 O2 H2O 112(4) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C2 1.384(4) . C1 C14 1.390(4) . C1 Cl1 1.743(3) . C2 C3 1.377(5) . C2 H2 0.9300 . C3 C4 1.382(5) . C3 H3 0.9300 . C4 C6 1.390(4) . C4 H4 0.9300 . C5 O1 1.449(3) . C5 C7 1.502(4) . C5 C6 1.503(4) . C5 H5 0.95(3) . C6 C14 1.398(4) . C7 C12 1.390(4) . C7 C8 1.394(4) . C8 C9 1.380(4) . C8 H8 0.9300 . C9 C10 1.373(4) . C9 H9 0.9300 . C10 C11 1.384(4) . C10 H10 0.9300 . C11 C12 1.391(4) . C11 Cl2 1.740(3) . C12 C13 1.511(4) . C13 O2 1.450(3) . C13 C14 1.508(4) . C13 H13 0.91(3) . O1 H1O 0.8199(11) . O2 H2O 0.8200(11) . 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 1.2(5) . . . . Cl1 C1 C2 C3 -178.4(2) . . . . C1 C2 C3 C4 0.3(5) . . . . C2 C3 C4 C6 -1.0(5) . . . . C3 C4 C6 C14 0.4(4) . . . . C3 C4 C6 C5 177.2(3) . . . . O1 C5 C6 C4 -98.9(3) . . . . C7 C5 C6 C4 142.0(3) . . . . O1 C5 C6 C14 78.1(3) . . . . C7 C5 C6 C14 -41.0(3) . . . . O1 C5 C7 C12 -80.5(3) . . . . C6 C5 C7 C12 40.3(3) . . . . O1 C5 C7 C8 97.8(3) . . . . C6 C5 C7 C8 -141.4(3) . . . . C12 C7 C8 C9 -0.2(4) . . . . C5 C7 C8 C9 -178.4(3) . . . . C7 C8 C9 C10 0.0(5) . . . . C8 C9 C10 C11 0.4(5) . . . . C9 C10 C11 C12 -0.7(4) . . . . C9 C10 C11 Cl2 178.0(2) . . . . C8 C7 C12 C11 -0.1(4) . . . . C5 C7 C12 C11 178.2(2) . . . . C8 C7 C12 C13 -179.4(3) . . . . C5 C7 C12 C13 -1.1(4) . . . . C10 C11 C12 C7 0.5(4) . . . . Cl2 C11 C12 C7 -178.1(2) . . . . C10 C11 C12 C13 179.8(3) . . . . Cl2 C11 C12 C13 1.2(4) . . . . C7 C12 C13 O2 84.8(3) . . . . C11 C12 C13 O2 -94.5(3) . . . . C7 C12 C13 C14 -36.7(3) . . . . C11 C12 C13 C14 144.1(3) . . . . C2 C1 C14 C6 -1.8(4) . . . . Cl1 C1 C14 C6 177.79(19) . . . . C2 C1 C14 C13 179.8(3) . . . . Cl1 C1 C14 C13 -0.6(4) . . . . C4 C6 C14 C1 1.0(4) . . . . C5 C6 C14 C1 -175.9(2) . . . . C4 C6 C14 C13 179.5(3) . . . . C5 C6 C14 C13 2.5(3) . . . . O2 C13 C14 C1 93.6(3) . . . . C12 C13 C14 C1 -145.9(3) . . . . O2 C13 C14 C6 -84.7(3) . . . . C12 C13 C14 C6 35.8(3) . . . .