Combined Experimental and Theoretical Study of Long-Range H F Interactions in α Fluoro Amides
Cosimi, Elena; Trapp, Nils; Ebert, Marc-Olivier; Wennemers, Helma; Chemical Communications  (2019) –; doi:10.1039/C8CC09987A

data_7122850
_publ_section_title
;
 Combined Experimental and Theoretical Study of Long-Range H F
 Interactions in \a Fluoro Amides
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09987A
_journal_year                    2019
_chemical_formula_moiety         'C9 H8 F2 O S'
_chemical_formula_sum            'C9 H8 F2 O S'
_chemical_formula_weight         202.21
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-23
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-12-13 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.2920(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.73090(10)
_cell_length_b                   15.2234(2)
_cell_length_c                   10.32150(10)
_cell_measurement_reflns_used    14430
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.9540
_cell_measurement_theta_min      5.8010
_cell_volume                     897.96(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_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     64.00  99.00   0.50    0.24    --   82.00  63.00  86.18   70
  2  \w    119.00 144.00   0.50    0.24    --   82.00  63.00  86.18   50
  3  \w     86.00 115.00   0.50    0.24    --  110.00  77.00  90.00   58
  4  \w    153.00 178.00   0.50    0.24    --  110.00  57.00 120.00   50
  5  \w    134.00 176.00   0.50    0.24    --  110.00  77.00 -30.00   84
  6  \w     87.00 131.00   0.50    0.24    --  110.00  77.00-180.00   88
  7  \w     95.00 133.00   0.50    0.24    --  110.00  57.00-180.00   76
  8  \w    137.00 177.00   0.50    0.24    --  110.00  57.00-180.00   80
  9  \w    124.00 164.00   0.50    0.24    --  110.00  77.00-150.00   80
 10  \w     89.00 115.00   0.50    0.24    --  110.00  77.00-150.00   52
 11  \w     86.00 113.00   0.50    0.24    --  110.00  77.00 -30.00   54
 12  \w     86.00 112.00   0.50    0.24    --  110.00  77.00 -60.00   52
 13  \w    125.00 172.00   0.50    0.24    --  110.00  77.00 -60.00   94
 14  \w    122.00 175.00   0.50    0.24    --  110.00  77.00  30.00  106
 15  \w     87.00 114.00   0.50    0.24    --  110.00  77.00  30.00   54
 16  \w     99.00 145.00   0.50    0.24    --  110.00  38.00  60.00   92
 17  \w     86.00 168.00   0.50    0.24    --  110.00  77.00 120.00  164
 18  \w     95.00 129.00   0.50    0.24    --  110.00  57.00 120.00   68
 19  \w     86.00 171.00   0.50    0.24    --  110.00  77.00   0.00  170
 20  \w     98.00 125.00   0.50    0.24    --  110.00  38.00 -30.00   54
 21  \w     86.00 112.00   0.50    0.24    --  110.00  77.00 -90.00   52
 22  \w    100.00 130.00   0.50    0.24    --  110.00  38.00-120.00   60
 23  \w    123.00 173.00   0.50    0.24    --  110.00  77.00 -90.00  100
 24  \w     94.00 130.00   0.50    0.24    --  110.00  57.00   0.00   72
 25  \w     86.00 134.00   0.50    0.24    --  110.00  77.00  60.00   96
 26  \w    144.00 175.00   0.50    0.24    --  110.00  77.00  60.00   62
 27  \w    124.00 176.00   0.50    0.24    --  110.00  77.00 150.00  104
 28  \w     86.00 112.00   0.50    0.24    --  110.00  77.00 150.00   52
 29  \w    102.00 141.00   0.50    0.24    --  110.00  57.00 -90.00   78
 30  \w     88.00 143.00   0.50    0.24    --  110.00  77.00-120.00  110
 31  \w     12.00  40.00   0.50    0.10    --   38.00  82.00  55.17   56
 32  \w     11.00  37.00   0.50    0.10    --   38.00  84.00  93.17   52
 33  \w     96.00 140.00   0.50    0.24    --  110.00  57.00 -30.00   88
 34  \w     12.00  38.00   0.50    0.10    --   38.00  83.00 131.59   52
 35  \w     13.00  41.00   0.50    0.10    --   38.00  81.00 178.34   56
 36  \w   -122.00 -35.00   0.50    0.10    --  -49.37 178.00 150.00  174
 37  \w    -93.00 -20.00   0.50    0.24    --  -70.00 125.00  90.00  146
 38  \w    132.00 176.00   0.50    0.24    --  110.00  77.00  90.00   88
 39  \w    100.00 127.00   0.50    0.24    --  110.00  38.00-180.00   54
 40  \w     24.00 113.00   0.50    0.10    --   46.00  73.00 -95.59  178
 41  \w     28.00 117.00   0.50    0.10    --   50.00  73.00 -68.41  178
 42  \w     29.00 117.00   0.50    0.10    --   50.00  72.00 -33.45  176
 43  \w     37.00 125.00   0.50    0.10    --   49.37  38.00 -90.00  176
 44  \w     37.00 125.00   0.50    0.10    --   49.37  19.00  60.00  176
 45  \w     92.00 118.00   0.50    0.24    --  110.00-125.00   0.00   52
 46  \w     46.00 108.00   0.50    0.24    --  110.00 -99.00  90.00  124
 47  \w     59.00  84.00   0.50    0.24    --  110.00-125.00   0.00   50
 48  \w     82.00 109.00   0.50    0.24    --  110.00 -99.00-180.00   54
 49  \w     40.00  77.00   0.50    0.24    --  110.00 -99.00-180.00   74
 50  \w     55.00  95.00   0.50    0.24    --  110.00 -99.00-150.00   80
 51  \w     45.00  92.00   0.50    0.24    --  110.00 -99.00 -90.00   94
 52  \w     42.00  97.00   0.50    0.24    --  110.00 -99.00   0.00  110
 53  \w     57.00 122.00   0.50    0.10    --   49.37-178.00 120.00  130
 54  \w    102.00 127.00   0.50    0.24    --  110.00 -77.00  30.00   50
 55  \w     49.00  76.00   0.50    0.24    --  110.00 -57.00  60.00   54
 56  \w     45.00  72.00   0.50    0.24    --  110.00 -77.00  30.00   54
 57  \w     44.00  69.00   0.50    0.24    --  110.00 -57.00 -30.00   50
 58  \w   -125.00 -37.00   0.50    0.10    --  -49.37 -19.00-180.00  176
 59  \w    -79.00 -51.00   0.50    0.24    --  -70.00 -67.00-114.88   56
 60  \w    -78.00 -50.00   0.50    0.24    --  -70.00 -68.00 -97.22   56
 61  \w    -83.00 -56.00   0.50    0.24    --  -70.00 -55.00 -53.15   54
 62  \w    -73.00 -48.00   0.50    0.24    --  -70.00 -72.00  32.19   50
 63  \w    -74.00 -48.00   0.50    0.24    --  -70.00 -73.00  80.50   52
 64  \w    -77.00 -51.00   0.50    0.24    --  -70.00 -66.00 107.06   52
 65  \w    -83.00 -50.00   0.50    0.24    --  -70.00 -71.00  51.01   66
 66  \w    -81.00 -49.00   0.50    0.24    --  -70.00 -71.00  13.22   64
 67  \w   -115.00 -89.00   0.50    0.24    --  -70.00 -72.00  32.19   52
 68  \w    -81.00 -50.00   0.50    0.24    --  -70.00 -71.00 163.03   62
 69  \w    -87.00 -49.00   0.50    0.24    --  -70.00 -71.00  -9.49   76
 70  \w    -85.00 -59.00   0.50    0.24    --  -70.00 -57.00 120.00   52
 71  \w    -80.00 -53.00   0.50    0.24    --  -70.00 -63.00 -77.16   54
 72  \w    -74.00 -48.00   0.50    0.24    --  -70.00 -73.00-160.22   52
 73  \w   -103.00 -48.00   0.50    0.24    --  -70.00 -73.00-138.34  110
 74  \w   -134.00 -99.00   0.50    0.24    --  -70.00 -73.00-160.22   70
 75  \w   -127.00 -38.00   0.50    0.10    --  -58.00 -67.00 139.12  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0156561000
_diffrn_orient_matrix_UB_12      0.0807464000
_diffrn_orient_matrix_UB_13      -0.0888232000
_diffrn_orient_matrix_UB_21      0.0613496000
_diffrn_orient_matrix_UB_22      0.0581917000
_diffrn_orient_matrix_UB_23      0.1199399000
_diffrn_orient_matrix_UB_31      0.2619985000
_diffrn_orient_matrix_UB_32      -0.0183653000
_diffrn_orient_matrix_UB_33      -0.0112785000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20439
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.623
_diffrn_reflns_theta_min         5.187
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.156
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.496
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.061
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0577P)^2^+0.9494P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1843
_reflns_number_total             1915
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09987a2.cif
_cod_data_source_block           w200318_1_1
_cod_database_code               7122850
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C9H8F2OS
_reflns_odcompleteness_completeness 100.00
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              15195
_olex2_date_sample_data_collection 2018-03-20
_olex2_date_sample_submission    2018-03-20
_olex2_submission_original_sample_id w200318_1_1
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.839