A metal-free strategy to construct fluoroalkyl-olefin linkages using fluoroalkanes.
Chakrabarti, Kaushik; Wade Wolfe, Michael M.; Guo, Shuo; Tucker, Joseph W.; Lee, Jisun; Szymczak, Nathaniel K.; Chemical science 15 (2024) 1752–1757; doi:10.1039/d3sc05616c

data_1570592
_publ_section_title
;
 A metal-free strategy to construct fluoroalkyl-olefin linkages using
 fluoroalkanes.
;
_journal_issue                   5
_journal_name_full               'Chemical science'
_journal_page_first              1752
_journal_page_last               1757
_journal_paper_doi               10.1039/d3sc05616c
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C17 H14 F2'
_chemical_formula_weight         256.28
_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     direct
_audit_creation_date             2023-04-18
_audit_creation_method
;FinalCif V128 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-10-06 deposited with the CCDC.	2023-12-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.67150(10)
_cell_length_b                   9.65100(10)
_cell_length_c                   15.2097(2)
_cell_measurement_reflns_used    12404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.2920
_cell_measurement_theta_min      5.0570
_cell_volume                     1272.88(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9958
_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   -110.00  70.00   1.00    1.00    --  -20.00   0.00-180.00  180
  2  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  3  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00   0.00   45
  4  \w    -25.00  43.00   1.00    1.00    --  -20.00  36.00 120.00   68
  5  \w    -45.00   0.00   1.00    1.00    --  -20.00  72.00-180.00   45
  6  \w   -173.00-128.00   1.00    3.00    --  -92.00 -36.00 120.00   45
  7  \w   -133.00 -88.00   1.00    3.00    --  -92.00 -36.00 -60.00   45
  8  \w   -104.00 -59.00   1.00    3.00    --  -92.00  36.00  60.00   45
  9  \w   -122.00 -77.00   1.00    3.00    --  -92.00 -72.00  60.00   45
 10  \w   -174.00 -78.00   1.00    3.00    --  -92.00 -72.00-120.00   96
 11  \w    -93.00 -35.00   1.00    3.00    --  -92.00  36.00-120.00   58
 12  \w   -176.00 -77.00   1.00    3.00    --  -92.00 -72.00 -60.00   99
 13  \w   -147.00 -75.00   1.00    3.00    --  -92.00 -72.00-180.00   72
 14  \w   -176.00 -77.00   1.00    3.00    --  -92.00 -72.00 120.00   99
 15  \w   -177.00-116.00   1.00    3.00    --  -92.00 -36.00  60.00   61
 16  \w    -87.00  -9.00   1.00    3.00    --  -92.00  36.00 -60.00   78
 17  \w   -102.00 -14.00   1.00    3.00    --  -92.00  36.00   0.00   88
 18  \w   -102.00 -21.00   1.00    3.00    --  -92.00  72.00 120.00   81
 19  \w   -175.00-104.00   1.00    3.00    --  -92.00 -36.00   0.00   71
 20  \w   -104.00 -52.00   1.00    3.00    --  -92.00  72.00  60.00   52
 21  \w   -109.00 -14.00   1.00    3.00    --  -92.00  72.00-120.00   95
 22  \w   -105.00 -24.00   1.00    3.00    --  -92.00  36.00-120.00   81
 23  \w   -105.00  -2.00   1.00    3.00    --  -92.00  36.00-180.00  103
 24  \w   -106.00  -2.00   1.00    3.00    --  -92.00  72.00 -60.00  104
 25  \w   -106.00  -2.00   1.00    3.00    --  -92.00  72.00 -60.00  104
 26  \w   -107.00 -29.00   1.00    3.00    --  -92.00  72.00   0.00   78
 27  \w   -117.00 -72.00   1.00    3.00    --  -92.00  72.00 180.00   45
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0113882000
_diffrn_orient_matrix_UB_12      0.0390536000
_diffrn_orient_matrix_UB_13      -0.0980451000
_diffrn_orient_matrix_UB_21      0.0638963000
_diffrn_orient_matrix_UB_22      0.1434534000
_diffrn_orient_matrix_UB_23      0.0254686000
_diffrn_orient_matrix_UB_31      0.1652542000
_diffrn_orient_matrix_UB_32      -0.0581432000
_diffrn_orient_matrix_UB_33      -0.0031003000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18902
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        66.9682
_diffrn_reflns_theta_max         69.2221
_diffrn_reflns_theta_min         2.9053
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 924 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(9)
_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     172
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0396
_refine_ls_R_factor_gt           0.0386
_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^)+(0.0601P)^2^+0.3723P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1038
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2318
_reflns_number_total             2376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05616c2.cif
_cod_data_source_block           KCRXN127
_cod_depositor_comments          'Adding full bibliography for 1570592.cif.'
_cod_database_code               1570592
_chemical_oxdiff_formula         C17H14F2
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_completeness 100.00
_oxdiff_exptl_absorpt_empirical_details
;Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.441
_oxdiff_exptl_absorpt_empirical_full_min 0.619
_cell_oxdiff_measurement_reflns_used 12404
_cell_oxdiff_volume              1272.88(6)
_cell_oxdiff_angle_gamma         90.005(2)
_cell_oxdiff_angle_beta          89.995(2)
_cell_oxdiff_angle_alpha         90.0170(18)
_cell_oxdiff_length_c            15.2009(4)
_cell_oxdiff_length_b            9.65027(18)
_cell_oxdiff_length_a            8.6771(3)
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              93529