The selectivity behaviour of 9,9′-bifluorenyl-9,9′-diol as a host compound for highly efficient separations of mixed pyridines
Groenewaldt, Jaime-lee; Barton, Benita; Hosten, Eric C.; CrystEngComm 27 (2025) 4176–4188; doi:10.1039/D5CE00432B

data_7250468
_publ_section_title
;
 The selectivity behaviour of 9,9&#x2032;-bifluorenyl-9,9&#x2032;-diol as
 a host compound for highly efficient separations of mixed pyridines
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4176
_journal_page_last               4188
_journal_paper_doi               10.1039/D5CE00432B
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C26 H18 O2, C6 H7 N'
_chemical_formula_sum            'C32 H25 N O2'
_chemical_formula_weight         455.53
_chemical_name_systematic        9,9'-bifluorenyl-9,9'-diol
_chemical_temperature_decomposition 353.65
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-04-22 deposited with the CCDC.	2025-05-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4369(5)
_cell_length_b                   10.7155(4)
_cell_length_c                   21.6126(9)
_cell_measurement_reflns_used    9451
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.17
_cell_volume                     2417.08(18)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service V6.2.16'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'Ortep-3 for Windows V2023.1 (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2019/3 (Sheldrick, 2015b) and ShelXle (H\"ubschle, 2011)'
_computing_structure_solution    'SHELXT-2019/3 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Bruker PHOTON II 7 CCD detector'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            74747
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_min         2.121
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             70
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.399
_exptl_crystal_size_mid          0.311
_exptl_crystal_size_min          0.257
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 2203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(16)
_refine_ls_extinction_coef       0.0055(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0310
_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^)+(0.0466P)^2^+0.2608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0835
_reflns_Friedel_coverage         0.770
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5265
_reflns_number_total             5532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00432b2.cif
_cod_data_source_block           bq124
_cod_depositor_comments
'Adding full bibliography for 7250467--7250469.cif.'
_cod_database_code               7250468
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.980
_exptl_absorpt_special_details
'Additional spherical absorption correction applied with mu*r =  0.20'
_shelx_res_checksum              81073