Organic fluorine mediated intermolecular interactions: insights from experimental and theoretical charge density analyses
Sakshi,; Gupta, Yogita; Robertson, Craig M.; Munshi, Parthapratim; Roy Choudhury, Angshuman; CrystEngComm 27 (2025) 478–487; doi:10.1039/D4CE00829D

data_7249460
_publ_section_title
;
 Organic fluorine mediated intermolecular interactions: insights from
 experimental and theoretical charge density analyses
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              478
_journal_page_last               487
_journal_paper_doi               10.1039/D4CE00829D
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C22 H17 F4 N O'
_chemical_formula_sum            'C22 H17 F4 N O'
_chemical_formula_weight         387.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-09-18
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-05-24 deposited with the CCDC.	2024-10-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.2015(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.07317(10)
_cell_length_b                   6.24689(4)
_cell_length_c                   35.5828(2)
_cell_measurement_reflns_used    166241
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      52.5340
_cell_measurement_theta_min      2.3220
_cell_volume                     3504.71(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (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      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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    -40.00  94.00   0.50    8.00    --    5.00  38.00-150.00  268
  2  \w    -32.00  94.00   0.50    8.00    --    5.00  68.00  60.00  252
  3  \w    -30.00  94.00   0.50    8.00    --    5.00  57.00 -30.00  248
  4  \w    -78.00  46.00   0.50    8.00    --  -43.10  57.00-180.00  248
  5  \w   -179.00 -45.00   0.50   30.00    --  -90.00 -38.00-150.00  268
  6  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00  30.00  252
  7  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00 -30.00  252
  8  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00 120.00  252
  9  \w   -179.00 -53.00   0.50   30.00    --  -90.00 -68.00 136.92  252
 10  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00   0.00  252
 11  \w   -179.00 -53.00   0.50   30.00    --  -90.00 -68.00  90.00  252
 12  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00-180.00  252
 13  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00  90.00  252
 14  \w   -179.00 -55.00   0.50   30.00    --  -90.00 -59.00-157.27  248
 15  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00 150.00  252
 16  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00 -90.00  252
 17  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00  60.00  252
 18  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00-150.00  252
 19  \w   -127.00  -1.00   0.50   30.00    --  -90.00  68.00 -60.00  252
 20  \w   -179.00 -55.00   0.50   30.00    --  -90.00 -63.00 153.85  248
 21  \w   -175.00 -72.00   0.50   30.00    --  -90.00 -50.00  65.82  206
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0124947000
_diffrn_orient_matrix_UB_12      -0.0064152000
_diffrn_orient_matrix_UB_13      -0.0202050000
_diffrn_orient_matrix_UB_21      0.0431841000
_diffrn_orient_matrix_UB_22      -0.0043512000
_diffrn_orient_matrix_UB_23      -0.0017101000
_diffrn_orient_matrix_UB_31      -0.0009685000
_diffrn_orient_matrix_UB_32      -0.1133638000
_diffrn_orient_matrix_UB_33      0.0012133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       79
_diffrn_reflns_limit_l_min       -79
_diffrn_reflns_number            213234
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         52.156
_diffrn_reflns_theta_min         2.334
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_description       block
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         20075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+0.5539P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18055
_reflns_number_total             20075
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00829d2.cif
_cod_data_source_block           u0162
_cod_depositor_comments          'Adding full bibliography for 7249460.cif.'
_cod_original_cell_volume        3504.72(4)
_cod_database_code               7249460
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C22 F2 H19 N O'
_chemical_oxdiff_usercomment     IQ-25-23
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C4(H4), C7(H7), C15(H15), C13(H13), C6(H6), C14(H14), C18(H18),
 C19(H19)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.592