Catalyst free synthesis of α-fluoro-β-hydroxy ketones/α-fluoro-ynols via electrophilic fluorination of tertiary propargyl alcohols using Selectfluor™ (F-TEDA-BF4).
Naveen, Naganaboina; Balamurugan, Rengarajan; Organic & biomolecular chemistry 15 (2017) 2063–2072; doi:10.1039/c7ob00140a

data_7155487
_publ_section_title
;
 Catalyst free synthesis of \a-fluoro-\b-hydroxy ketones/\a-fluoro-ynols
 via electrophilic fluorination of tertiary propargyl alcohols using
 Selectfluor&#x2122; (F-TEDA-BF4).
;
_journal_issue                   9
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2063
_journal_page_last               2072
_journal_paper_doi               10.1039/c7ob00140a
_journal_volume                  15
_journal_year                    2017
_chemical_formula_moiety         'C21 H17 F O2'
_chemical_formula_sum            'C21 H17 F O2'
_chemical_formula_weight         320.35
_chemical_melting_point          424
_chemical_name_systematic        2-Fluoro-3-hydroxy-1,3,3-triphenylpropan-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_audit_update_record
;
2016-09-04 deposited with the CCDC.
2017-02-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.281(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0818(3)
_cell_length_b                   5.99520(10)
_cell_length_c                   18.5272(4)
_cell_measurement_reflns_used    2567
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5730
_cell_measurement_theta_min      4.2480
_cell_volume                     1636.86(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    SHELXL-97
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.3291
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
  1 omega   35.00   66.00   1.0000    6.6400
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 31

  2 omega  -44.00    8.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000   60.0000 52

  3 omega -110.00  -51.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -90.0000 59

  4 omega  -93.00  -68.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000 -180.0000 25

  5 omega  -49.00   15.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000    0.0000 64

  6 omega  -27.00    0.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  125.0000 -180.0000 27

  7 omega  -21.00   25.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000   60.0000 46

  8 omega   50.00   84.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -       54.8467  -77.0000  -90.0000 34

  9 omega   39.00   92.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -25.0000  120.0000 53

 10 omega   77.00  103.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934 -111.0000   90.0000 26

 11 omega   39.00   94.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -25.0000 -120.0000 55

 12 omega  145.00  173.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934    0.0000  -30.0000 28

 13 omega   46.00  115.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934    0.0000  -30.0000 69

 14 omega   43.00  105.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -50.0000    0.0000 62

 15 omega   56.00  104.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934 -111.0000  -30.0000 48

 16 omega   45.00  109.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -63.0000  -60.0000 64

 17 omega   37.00   85.00   1.0000   24.5500
omega____ theta____ kappa____ phi______ frames
    -      109.6934  -37.0000  120.0000 48
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0990093000
_diffrn_orient_matrix_UB_12      0.0256555000
_diffrn_orient_matrix_UB_13      -0.0081285000
_diffrn_orient_matrix_UB_21      -0.0330892000
_diffrn_orient_matrix_UB_22      0.0476661000
_diffrn_orient_matrix_UB_23      -0.0830902000
_diffrn_orient_matrix_UB_31      -0.0038889000
_diffrn_orient_matrix_UB_32      0.2512324000
_diffrn_orient_matrix_UB_33      0.0166193000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0112
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5097
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.438
_diffrn_reflns_theta_min         3.441
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.734
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3106
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0424
_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^)+(0.0690P)^2^+0.2598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2719
_reflns_number_total             3106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ob00140a2.cif
_cod_data_source_block           rb36nnk2
_cod_depositor_comments          'Adding full bibliography for 7155487.cif.'
_cod_database_code               7155487
_chemical_oxdiff_formula         'C23 H23 O23 F23'
_chemical_oxdiff_usercomment     NAVEEN
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C7(H7), C21(H21), C17(H17), C8(H8), C11(H11), C6(H6),
 C19(H19), C15(H15), C14(H14), C12(H12), C13(H13), C18(H18), C20(H20)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              19109
_shelx_shelxl_version_number     2014/8
_olex2_submission_special_instructions 'No special instructions were received'