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_7250548
_publ_section_title
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 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         'C11 H7 F13 N2'
_chemical_formula_sum            'C11 H7 F13 N2'
_chemical_formula_weight         414.19
_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             2023-02-17
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-01-16 deposited with the CCDC.	2025-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.196(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8130(4)
_cell_length_b                   5.42950(10)
_cell_length_c                   11.1728(2)
_cell_measurement_reflns_used    4935
_cell_measurement_temperature    110.00(10)
_cell_measurement_theta_max      75.9790
_cell_measurement_theta_min      3.7010
_cell_volume                     1440.69(4)
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      110.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.953
_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    -84.00 -22.00   0.50    4.00    --  -48.70 122.00 -72.00  124
  2  \w   -119.00 -57.00   0.50    4.00    --  -48.70-151.00  44.00  124
  3  \w     55.00  89.00   0.50    4.00    --   48.70-122.00-154.00   68
  4  \w    136.00 176.00   0.50   16.00    --  107.75 122.00 -72.00   80
  5  \w     89.00 125.00   0.50   16.00    --  107.75-151.00  44.00   72
  6  \w     50.00  75.00   0.50   16.00    --  107.75-122.00-154.00   50
  7  \w    102.00 131.00   0.50   16.00    --  107.75 122.00 -72.00   58
  8  \w   -116.00 -74.00   0.50    4.00    --  -48.70-125.00-120.00   84
  9  \w   -110.00 -82.00   0.50    4.00    --  -48.70-125.00 -90.00   56
 10  \w   -103.00 -41.00   0.50    4.00    --  -48.70 -37.00  60.00  124
 11  \w   -120.00 -50.00   0.50    4.00    --  -48.70 -57.00-180.00  140
 12  \w     38.00 106.00   0.50   16.00    --  107.75 -99.00-150.00  136
 13  \w     95.00 163.00   0.50   16.00    --  107.75  37.00-180.00  136
 14  \w     95.00 124.00   0.50   16.00    --  107.75  37.00  30.00   58
 15  \w     41.00 112.00   0.50   16.00    --  107.75 -57.00   0.00  142
 16  \w    128.00 153.00   0.50   16.00    --  107.75  37.00  30.00   50
 17  \w     75.00 102.00   0.50   16.00    --  107.75 -99.00 -90.00   54
 18  \w     37.00 118.00   0.50   16.00    --  107.75 -37.00 -30.00  162
 19  \w     88.00 134.00   0.50   16.00    --  107.75 151.00  88.00   92
;
_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      0.0592145000
_diffrn_orient_matrix_UB_12      0.1146965000
_diffrn_orient_matrix_UB_13      0.0176452000
_diffrn_orient_matrix_UB_21      -0.0255581000
_diffrn_orient_matrix_UB_22      0.2578131000
_diffrn_orient_matrix_UB_23      -0.0228394000
_diffrn_orient_matrix_UB_31      -0.0072272000
_diffrn_orient_matrix_UB_32      0.0285778000
_diffrn_orient_matrix_UB_33      0.1351962000
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8586
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.630
_diffrn_reflns_theta_min         3.722
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.169
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82485
_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    1.910
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0379
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0506P)^2^+0.9734P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2482
_reflns_number_total             2882
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cp01737h3.cif
_cod_data_source_block           dwb23002
_cod_database_code               7250548
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H8 F13 N2'
_chemical_oxdiff_usercomment     'Joshua Lai JL-032'
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.501
_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:
 C1(H1), C3(H3), C2(H2)
;
_shelx_res_checksum              9411
_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 1.245
_oxdiff_exptl_absorpt_empirical_full_min 0.742