The conformations of new CF3 and CF3-CHF containing amides derived from carbohydrates: NMR, crystallographic and DFT study
Bilska-Markowska, Monika; Siodła, Tomasz; Patyk, Ewa; Katrusiak, Andrzej; Koroniak, Henryk; New J. Chem. 41 (2017) 12631–12644; doi:10.1039/C7NJ02986A

data_7056613
_publ_section_title
;
 The conformations of new CF3 and CF3-CHF containing amides derived from
 carbohydrates: NMR, crystallographic and DFT study
;
_journal_issue                   21
_journal_name_full               'New J. Chem.'
_journal_page_first              12631
_journal_page_last               12644
_journal_paper_doi               10.1039/C7NJ02986A
_journal_volume                  41
_journal_year                    2017
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C19 H23 F4 N O5'
_chemical_formula_sum            'C19 H23 F4 N O5'
_chemical_formula_weight         421.38
_chemical_name_systematic
5-(N-benzyl)amino-5-deoxy-1,2-O-isopropylidene-3-O-methyl-a-D-xylo-furanosyl)-(R,S)-2,3,3,3-tetrafluoropropanamide
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2017-04-12 deposited with the CCDC.
2017-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                73.389(3)
_cell_angle_beta                 72.298(4)
_cell_angle_gamma                84.890(4)
_cell_formula_units_Z            1
_cell_length_a                   6.0766(4)
_cell_length_b                   9.4360(3)
_cell_length_c                   9.7318(4)
_cell_measurement_reflns_used    5511
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      73.9380
_cell_measurement_theta_min      4.8680
_cell_volume                     509.40(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5357
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega    0.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   90.0000  -54.0860 25

  2 omega  -51.00  -11.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5879  -57.0000   90.0000 40

  3 omega  -97.00   -3.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5879  125.0000  -90.0000 94

  4 omega -115.00  -57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5879  -57.0000   90.0000 58

  5 omega   49.00  115.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5879   37.0000 -120.0000 66

  6 omega   14.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5879   37.0000 -120.0000 31

  7 omega  -38.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5879  -77.0000  120.0000 112

  8 omega   12.00   39.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5879   57.0000 -150.0000 27

  9 omega   10.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  -56.4379 25

 10 omega   11.00   36.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   82.0000    2.4383 25

 11 omega   10.00   36.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   85.0000   56.3038 26

 12 omega   11.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  -33.7212 27

 13 omega   16.00   45.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   81.0000 -142.7281 29

 14 omega   10.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  139.4277 25

 15 omega  -87.00  -39.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -75.0000  -37.4201 48

 16 omega  -82.00  -37.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -74.0000   37.6717 45

 17 omega -122.00  -89.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -74.0000   37.6717 33

 18 omega -122.00  -95.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -77.0000 -165.2800 27

 19 omega  -66.00  -36.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -70.0000  -77.0000 -165.2800 30

 20 omega  -66.00  -41.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -72.0000  148.0633 25

 21 omega  -67.00  -41.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -73.0000  105.3391 26

 22 omega -150.00 -114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -74.0000  -73.0000  105.3391 36

 23 omega  -71.00  -45.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -72.0000 -101.0152 26

 24 omega  -78.00  -45.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -72.0000  -71.4933 33

 25 omega  -77.00  -45.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -78.0000  -72.0000    4.8705 32

 26 omega  -86.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  120.0000 36

 27 omega  -84.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   30.0000 34

 28 omega  -77.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -74.0000 -113.7276 27

 29 omega  -77.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -75.0000  -54.8740 27

 30 omega  -78.00  -51.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -75.0000  -84.6393 27

 31 omega  -76.00  -27.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000   45.0000  120.0000 49

 32 omega  -78.00  -51.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -68.0000   86.0731 27

 33 omega  -90.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000  150.0000 41

 34 omega  -76.00  -51.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -69.0000   57.5236 25

 35 omega  -81.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -150.0000 31

 36 omega  -85.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -180.0000 36

 37 omega  -74.00  -49.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000   90.0000 25

 38 omega -144.00 -117.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -69.0000   57.5236 27

 39 omega -102.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -75.0000   -7.8796 52

 40 omega  -83.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -73.0000   38.9362 33

 41 omega  -77.00  -50.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -83.0000  -77.0000 -120.0000 27

 42 omega   38.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   90.0000 25

 43 omega   42.00   69.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 27

 44 omega   79.00  156.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 77

 45 omega   82.00  137.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 55

 46 omega  121.00  149.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 28

 47 omega   83.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 27

 48 omega   85.00  112.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 27

 49 omega   53.00   81.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -150.0000 28

 50 omega   80.00  136.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 56

 51 omega   36.00   86.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   60.0000 50

 52 omega   83.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 32

 53 omega   80.00  110.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 30

 54 omega  114.00  152.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 38

 55 omega  109.00  136.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 27

 56 omega   90.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 26

 57 omega  119.00  155.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 36

 58 omega   88.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -90.0000 27

 59 omega   37.00   85.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000 -180.0000 48

 60 omega   79.00  135.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 56

 61 omega   61.00   91.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 30

 62 omega   85.00  112.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 27

 63 omega   36.00   64.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -150.0000 28

 64 omega   88.00  115.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 27

 65 omega   45.00   79.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   30.0000 34

 66 omega   36.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 32

 67 omega   41.00   68.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 27

 68 omega   29.00  109.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -120.0000 80

 69 omega   89.00  125.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 36

 70 omega   85.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 36

 71 omega  125.00  152.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 27

 72 omega   80.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

 73 omega   35.00   60.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 25

 74 omega   68.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000    0.0000 46

 75 omega  120.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 37

 76 omega   44.00   83.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  120.0000 39

 77 omega   85.00  111.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 26

 78 omega  129.00  156.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   30.0000 27

 79 omega  133.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 25

 80 omega   79.00  105.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 26

 81 omega   87.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 27

 82 omega   91.00  116.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 25

 83 omega  114.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 43

 84 omega   38.00   83.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -111.0000   90.0000 45

 85 omega  125.00  158.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 33

 86 omega   80.00  113.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 33

 87 omega   82.00  121.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 39

 88 omega   87.00  122.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 35

 89 omega   35.00   63.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -60.0000 28

 90 omega  120.00  151.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 31

 91 omega   49.00  108.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000   90.0000 59

 92 omega  116.00  154.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 38

 93 omega   87.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 27

 94 omega  120.00  150.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -180.0000 30

 95 omega   81.00  118.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 37

 96 omega  127.00  157.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 30

 97 omega   87.00  114.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 27

 98 omega   87.00  112.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 25

 99 omega   33.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000 -150.0000 44

100 omega   36.00   99.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -94.0000  -60.0000 63

101 omega    1.00   34.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   87.0000 -176.3199 33

102 omega    0.00   32.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       38.0000   90.0000   92.5541 32

103 omega -119.00   -7.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5879  -77.0000    0.0000 112

104 omega -113.00  -66.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5879 -137.0000  144.0000 47

105 omega  -33.00   70.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5879  -57.0000   30.0000 103

106 omega  -41.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5879  -19.0000 -180.0000 128

107 omega   10.00   36.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   85.0000   56.3038 26

108 omega   10.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  -56.4379 28

109 omega   10.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   84.0000  139.4277 28

110 omega   11.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       46.0000   81.0000 -142.7281 35

111 omega   36.00  149.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       70.0000   77.0000 -126.7031 113
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0000932000
_diffrn_orient_matrix_UB_12      -0.1699439000
_diffrn_orient_matrix_UB_13      0.0583768000
_diffrn_orient_matrix_UB_21      -0.0823643000
_diffrn_orient_matrix_UB_22      0.0116597000
_diffrn_orient_matrix_UB_23      0.1625530000
_diffrn_orient_matrix_UB_31      -0.2530572000
_diffrn_orient_matrix_UB_32      -0.0033111000
_diffrn_orient_matrix_UB_33      0.0000909000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12459
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.489
_diffrn_reflns_theta_min         4.891
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       irregular
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.690
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1460 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         4002
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.139
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0782
_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^)+(0.1830P)^2^+0.0340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2411
_refine_ls_wR_factor_ref         0.2534
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.936
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                3480
_reflns_number_total             4002
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7nj02986a2.cif
_cod_data_source_block           10a
_cod_original_cell_volume        509.41(4)
_cod_database_code               7056613
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C19 H22 O5 F4 N1'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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. Restrained distances
 F1-C2
 1.32 with sigma of 0.005
 F4-C3
 1.32 with sigma of 0.005
 F2-C3
 1.32 with sigma of 0.005
 F3-C3
 1.32 with sigma of 0.005
 C1-C2
 1.5 with sigma of 0.02
3. Others
 Fixed U11: C2(0.324227) C3(0.309125)
4.a Ternary CH refined with riding coordinates:
 C2(H2), C12(H12), C13(H13), C14(H14), C15(H15)
4.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10)
4.d Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10)
4.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_shelx_res_checksum              62719
_olex2_submission_special_instructions 'No special instructions were received'