Selectivity considerations of host compound trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid when presented with pyridine and picoline mixtures: charge-assisted versus classical hydrogen bonding
Barton, Benita; Caira, Mino R.; Senekal, Ulrich; Hosten, Eric Cyriel; CrystEngComm  (2022) –; doi:10.1039/D2CE00327A

data_7245010
_publ_section_title
;
 Selectivity considerations of host compound
 trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid when
 presented with pyridine and picoline mixtures: charge-assisted versus
 classical hydrogen bonding
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00327A
_journal_year                    2022
_chemical_formula_moiety         'C18 H14 O4, 2(C5 H5 N)'
_chemical_formula_sum            'C28 H24 N2 O4'
_chemical_formula_weight         452.49
_chemical_melting_point          513.15
_chemical_name_systematic
'trans-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-01-25 deposited with the CCDC.	2022-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.3469(10)
_cell_length_b                   11.0693(7)
_cell_length_c                   25.0564(14)
_cell_measurement_reflns_used    9494
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.33
_cell_volume                     4811.3(5)
_computing_cell_refinement       'APEX2 v2011.4-1 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2011.4.0.0'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2018/3 (Sheldrick, 2015) and ShelXle (H\"ubschle, 2011)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            84933
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.378
_diffrn_reflns_theta_min         1.625
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9456
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1904
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pyridine'
_exptl_crystal_size_max          0.665
_exptl_crystal_size_mid          0.603
_exptl_crystal_size_min          0.284
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         6023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0503
_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^)+(0.0494P)^2^+2.3094P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1375
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4598
_reflns_number_total             6023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00327a1.cif
_cod_data_source_block           ja216
_cod_database_code               7245010
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.946
_shelx_estimated_absorpt_t_max   0.976
_shelx_res_checksum              22604