To Mix or Not to Mix: Charge and Polarity Effects on Alkyl/Fluoroalkyl Compound Miscibility§
Lai, Joshua; Gladden-Bennett, Evelyn F.; Shimizu, Karina; Elstone, Naomi; Tanner, Theo; Demé, Bruno; Whitwood, Adrian Charles; Shimizu, Seishi; Lopes, José N.C; Slattery, John M.; Bruce, Duncan W.; Physical Chemistry Chemical Physics  (2025) –; doi:10.1039/D5CP01737H

data_7250549
_publ_section_title
;
 To Mix or Not to Mix: Charge and Polarity Effects on Alkyl/Fluoroalkyl
 Compound Miscibility&#x00A7;
;
_journal_name_full               'Physical Chemistry Chemical Physics'
_journal_paper_doi               10.1039/D5CP01737H
_journal_year                    2025
_chemical_formula_moiety         'C13 H7 F17 N2'
_chemical_formula_sum            'C13 H7 F17 N2'
_chemical_formula_weight         514.21
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-06-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2025-01-16 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.232(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.1835(5)
_cell_length_b                   5.56120(10)
_cell_length_c                   10.3336(2)
_cell_measurement_reflns_used    8505
_cell_measurement_temperature    110.00(14)
_cell_measurement_theta_max      76.5770
_cell_measurement_theta_min      8.0890
_cell_volume                     1731.80(5)
_computing_cell_refinement       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(14)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -118.00 -41.00   0.50    3.00    --  -47.17-178.00  30.00  154
  2  \w   -118.00 -32.00   0.50    3.00    --  -47.17 -57.00  30.00  172
  3  \w    -54.00 -18.00   0.50    3.00    --  -47.17  37.00-180.00   72
  4  \w     27.00  53.00   0.50    3.00    --   47.17 -37.00 -60.00   52
  5  \w     40.00  93.00   0.50    3.00    --   47.17  37.00 -90.00  106
  6  \w    -24.00  21.00   0.50    3.00    --   47.17 -37.00 -60.00   90
  7  \w    -18.00   8.00   0.50    3.00    --   47.17 -57.00-120.00   52
  8  \w     13.00  62.00   0.50    3.00    --   47.17 -57.00-120.00   98
  9  \w     93.00 175.00   0.50   12.00    --  107.75  57.00 -90.00  164
 10  \w    135.00 177.00   0.50   12.00    --  107.75  19.00  90.00   84
 11  \w     60.00 104.00   0.50   12.00    --  107.75-125.00  90.00   88
 12  \w     39.00  90.00   0.50   12.00    --  107.75 -99.00 150.00  102
 13  \w     39.00  65.00   0.50   12.00    --  107.75 -77.00-150.00   52
 14  \w     94.00 177.00   0.50   12.00    --  107.75  57.00-120.00  166
 15  \w     39.00 108.00   0.50   12.00    --  107.75 -19.00  90.00  138
 16  \w     61.00 106.00   0.50   12.00    --  107.75 -99.00 120.00   90
 17  \w     43.00 119.00   0.50   12.00    --  107.75 -57.00 -60.00  152
 18  \w     75.00 102.00   0.50   12.00    --  107.75 -99.00 -30.00   54
 19  \w     37.00  69.00   0.50   12.00    --  107.75 -99.00 -30.00   64
 20  \w     43.00  77.00   0.50   12.00    --  107.75-125.00 -30.00   68
 21  \w     71.00 109.00   0.50   12.00    --  107.75-125.00  60.00   76
 22  \w     95.00 121.00   0.50   12.00    --  107.75  19.00  90.00   52
 23  \w     49.00 102.00   0.50   12.00    --  107.75 -99.00-150.00  106
 24  \w    100.00 125.00   0.50   12.00    --  107.75 -77.00-150.00   50
 25  \w     38.00 147.00   0.50   12.00    --  107.75   0.00  60.00  218
 26  \w     69.00 105.00   0.50   12.00    --  107.75 -99.00-120.00   72
 27  \w     38.00  70.00   0.50   12.00    --  107.75 -99.00  90.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0273385000
_diffrn_orient_matrix_UB_12      0.2327380000
_diffrn_orient_matrix_UB_13      0.0179183000
_diffrn_orient_matrix_UB_21      -0.0403717000
_diffrn_orient_matrix_UB_22      0.1482118000
_diffrn_orient_matrix_UB_23      -0.0514780000
_diffrn_orient_matrix_UB_31      -0.0154004000
_diffrn_orient_matrix_UB_32      0.0248908000
_diffrn_orient_matrix_UB_33      0.1389669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13768
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.000
_diffrn_reflns_theta_min         4.402
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.306
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.972
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.556
_refine_diff_density_min         -0.441
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0809
_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^)+(0.1171P)^2^+4.9319P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2490
_refine_ls_wR_factor_ref         0.2506
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3319
_reflns_number_total             3550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp01737h3.cif
_cod_data_source_block           dwb23011
_cod_database_code               7250549
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H7 F17 N2'
_chemical_oxdiff_usercomment     'Joshua Lai JL-096-1'
_shelx_estimated_absorpt_t_max   0.754
_shelx_estimated_absorpt_t_min   0.410
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C1(H1)
;
_shelx_res_checksum              49329
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.424
_oxdiff_exptl_absorpt_empirical_full_min 0.550