Extremely effective separations of pyridine/picoline mixtures through supramolecular chemistry strategies employing (4R,5R)-bis(diphenylhydroxymethyl)-2-spiro-1′-cyclohexane-1,3-dioxolane as the host compound
Recchia, Daniella L.; Barton, Benita; Hosten, Eric C.; CrystEngComm 27 (2025) 1960–1976; doi:10.1039/D5CE00111K

data_7250031
_publ_section_title
;
 Extremely effective separations of pyridine/picoline mixtures through
 supramolecular chemistry strategies employing
 (4R,5R)-bis(diphenylhydroxymethyl)-2-spiro-1&#x2032;-cyclohexane-1,3-dioxolane
 as the host compound
;
_journal_issue                   13
_journal_name_full               CrystEngComm
_journal_page_first              1960
_journal_page_last               1976
_journal_paper_doi               10.1039/D5CE00111K
_journal_volume                  27
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C34 H34 O4, C6 H7 N'
_chemical_formula_sum            'C40 H41 N O4'
_chemical_formula_weight         599.74
_chemical_name_systematic
(4R,5R)-Bis(diphenyldioxymethyl)-2-spiro-1'-cyclohexane-1,3-dioxane
_chemical_temperature_decomposition 352.31
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-03-18 deposited with the CCDC.	2025-02-26 downloaded from the CCDC.
;
_cell_angle_alpha                97.408(2)
_cell_angle_beta                 100.565(2)
_cell_angle_gamma                90.588(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5704(6)
_cell_length_b                   9.8658(5)
_cell_length_c                   17.3649(10)
_cell_measurement_reflns_used    9287
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.97
_cell_volume                     1597.37(16)
_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 (Farrugia, 2012)'
_computing_publication_material
'PLATON (Spek, 2009) and MERCURY (Macrae, 2008)'
_computing_structure_refinement
'SHELXL-2019/2 (Sheldrick, 2015b)  and ShelXle (H\"ubschle, 2011)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2015a)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'Bruker PHOTON II 7 detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            135115
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.307
_diffrn_reflns_theta_min         2.083
_diffrn_source                   'sealed x-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             70
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9597
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2016/2 (Krause, 2015)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             640
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 3-methylpyridine'
_exptl_crystal_size_max          0.555
_exptl_crystal_size_mid          0.491
_exptl_crystal_size_min          0.260
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 6468 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(14)
_refine_ls_extinction_coef       0.0132(12)
_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   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     818
_refine_ls_number_reflns         15818
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0274P)^2^+0.4768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.991
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                14346
_reflns_number_total             15818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00111k2.cif
_cod_data_source_block           aq103
_cod_depositor_comments
'Adding full bibliography for 7250028--7250031.cif.'
_cod_original_cell_volume        1597.38(16)
_cod_database_code               7250031
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.980
_shelx_res_checksum              27892