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_7245008
_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 H13 O4, C6 H8 N'
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42
_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           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-02-21 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            4
_cell_length_a                   16.5185(6)
_cell_length_b                   9.3246(3)
_cell_length_c                   12.6580(5)
_cell_measurement_reflns_used    9922
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.47
_cell_volume                     1949.69(12)
_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      200(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            24702
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.466
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9143
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 2-methylpyridine'
_exptl_crystal_size_max          0.599
_exptl_crystal_size_mid          0.503
_exptl_crystal_size_min          0.426
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2032 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4846
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0317
_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^)+(0.0516P)^2^+0.1874P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4489
_reflns_number_total             4846
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00327a1.cif
_cod_data_source_block           ma033
_cod_database_code               7245008
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.963
_shelx_res_checksum              44882