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_7122851
_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         'C11 H12 F N O3'
_chemical_formula_sum            'C11 H12 F N O3'
_chemical_formula_weight         225.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2018-12-13 deposited with the CCDC.
2019-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.53280(10)
_cell_length_b                   10.29960(10)
_cell_length_c                   23.8575(3)
_cell_measurement_reflns_used    32164
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      79.4320
_cell_measurement_theta_min      3.6590
_cell_volume                     2096.70(4)
_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  'ShelXL (Sheldrick, 2015)'
_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 0.992
_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    -51.00  41.00   0.50    0.23    --  -26.00  80.00-144.21  184
  2  \w      4.00  30.00   0.50    0.23    --   34.00  90.00-133.72   52
  3  \w     37.00 125.00   0.50    0.23    --   49.37  38.00 -30.00  176
  4  \w     68.00 155.00   0.50    0.93    --   82.00  53.00  11.58  174
  5  \w    138.00 164.00   0.50    0.93    --  110.00  77.00 -30.00   52
  6  \w    147.00 177.00   0.50    0.93    --  110.00  38.00 -30.00   60
  7  \w    135.00 176.00   0.50    0.93    --  110.00  77.00  60.00   82
  8  \w    141.00 173.00   0.50    0.93    --  110.00  77.00  90.00   64
  9  \w    132.00 169.00   0.50    0.93    --  110.00  77.00 150.00   74
 10  \w    128.00 172.00   0.50    0.93    --  110.00  77.00 120.00   88
 11  \w    132.00 178.00   0.50    0.93    --  110.00  38.00 150.00   92
 12  \w     96.00 130.00   0.50    0.93    --  110.00  57.00  30.00   68
 13  \w    119.00 167.00   0.50    0.93    --  110.00  77.00   0.00   96
 14  \w    103.00 142.00   0.50    0.93    --  110.00  38.00 -90.00   78
 15  \w    128.00 166.00   0.50    0.93    --  110.00  77.00-150.00   76
 16  \w     99.00 136.00   0.50    0.93    --  110.00  38.00-120.00   74
 17  \w     99.00 126.00   0.50    0.93    --  110.00  38.00 -60.00   54
 18  \w     98.00 135.00   0.50    0.93    --  110.00  38.00 -30.00   74
 19  \w     99.00 126.00   0.50    0.93    --  110.00  38.00  30.00   54
 20  \w    103.00 178.00   0.50    0.93    --  110.00  38.00  90.00  150
 21  \w     97.00 132.00   0.50    0.93    --  110.00  57.00 150.00   70
 22  \w     98.00 128.00   0.50    0.93    --  110.00  38.00 150.00   60
 23  \w     99.00 147.00   0.50    0.93    --  110.00  38.00 120.00   96
 24  \w     86.00 173.00   0.50    0.93    --  110.00  77.00  30.00  174
 25  \w     86.00 177.00   0.50    0.93    --  110.00  77.00 -90.00  182
 26  \w    100.00 129.00   0.50    0.93    --  110.00  38.00-150.00   58
 27  \w     86.00 177.00   0.50    0.93    --  110.00  77.00-180.00  182
 28  \w     86.00 177.00   0.50    0.93    --  110.00  77.00-120.00  182
 29  \w     86.00 134.00   0.50    0.93    --  110.00  77.00 -30.00   96
 30  \w     86.00 176.00   0.50    0.93    --  110.00  77.00 -60.00  180
 31  \w     86.00 114.00   0.50    0.93    --  110.00  77.00 120.00   56
 32  \w     86.00 127.00   0.50    0.93    --  110.00  77.00 150.00   82
 33  \w     86.00 112.00   0.50    0.93    --  110.00  77.00  90.00   52
 34  \w     87.00 129.00   0.50    0.93    --  110.00  77.00  60.00   84
 35  \w     87.00 112.00   0.50    0.93    --  110.00  77.00   0.00   50
 36  \w     58.00 145.00   0.50    0.23    --   74.00  59.00  29.48  174
 37  \w     59.00 120.00   0.50    0.23    --   49.37 178.00 150.00  122
 38  \w     25.00 113.00   0.50    0.23    --   46.00  72.00  85.71  176
 39  \w     34.00 121.00   0.50    0.23    --   49.37  57.00   0.00  174
 40  \w     38.00  84.00   0.50    0.93    --  110.00 -57.00 -30.00   92
 41  \w     44.00 109.00   0.50    0.93    --  110.00 -99.00   0.00  130
 42  \w     92.00 120.00   0.50    0.93    --  110.00-125.00   0.00   56
 43  \w     57.00 122.00   0.50    0.23    --   49.37-178.00  60.00  130
 44  \w     63.00 106.00   0.50    0.93    --  110.00 -99.00 120.00   86
 45  \w     38.00  84.00   0.50    0.93    --  110.00 -57.00  30.00   92
 46  \w     43.00 104.00   0.50    0.93    --  110.00 -99.00  60.00  122
 47  \w     59.00  85.00   0.50    0.93    --  110.00-125.00   0.00   52
 48  \w     51.00 109.00   0.50    0.93    --  110.00 -77.00-120.00  116
 49  \w     61.00 116.00   0.50    0.93    --  110.00-125.00-180.00  110
 50  \w     44.00  78.00   0.50    0.93    --  110.00 -57.00-180.00   68
 51  \w     44.00 110.00   0.50    0.93    --  110.00 -99.00-150.00  132
 52  \w     86.00 122.00   0.50    0.93    --  110.00  77.00-150.00   72
 53  \w     -3.00  23.00   0.50    0.23    --   30.00  97.00  88.91   52
 54  \w     29.00 117.00   0.50    0.23    --   50.00  72.00 172.68  176
 55  \w    -40.00  48.00   0.50    0.23    --  -26.00  49.00  80.31  176
 56  \w    -94.00  -3.00   0.50    0.93    --  -70.00  77.00-120.00  182
 57  \w   -121.00 -34.00   0.50    0.23    --  -49.37 -57.00 -60.00  174
 58  \w   -121.00 -32.00   0.50    0.23    --  -54.00 -73.00   7.97  178
 59  \w   -121.00 -32.00   0.50    0.23    --  -54.00 -72.00 158.93  178
 60  \w   -125.00 -37.00   0.50    0.23    --  -58.00 -71.00  76.78  176
 61  \w   -125.00 -37.00   0.50    0.23    --  -58.00 -71.00 -37.21  176
 62  \w   -125.00 -37.00   0.50    0.23    --  -58.00 -71.00 -75.30  176
 63  \w   -125.00 -36.00   0.50    0.23    --  -58.00 -72.00-123.17  178
 64  \w   -138.00 -50.00   0.50    0.93    --  -70.00 -68.00 -30.73  176
 65  \w   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00 140.49  178
 66  \w   -140.00 -52.00   0.50    0.93    --  -70.00 -62.00  94.49  176
 67  \w   -138.00 -49.00   0.50    0.93    --  -70.00 -69.00 -92.67  178
 68  \w   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00-145.21  178
 69  \w   -137.00 -48.00   0.50    0.93    --  -70.00 -73.00-176.45  178
 70  \w   -137.00 -49.00   0.50    0.93    --  -70.00 -71.00-162.86  176
 71  \w   -137.00 -48.00   0.50    0.93    --  -70.00 -73.00-112.77  178
 72  \w   -139.00 -51.00   0.50    0.93    --  -70.00 -65.00 -90.15  176
 73  \w   -137.00 -49.00   0.50    0.93    --  -70.00 -71.00  73.48  176
 74  \w   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00  24.39  178
 75  \w   -139.00 -50.00   0.50    0.93    --  -70.00 -67.00  45.63  178
 76  \w   -137.00 -48.00   0.50    0.93    --  -70.00 -72.00 150.39  178
 77  \w   -138.00 -50.00   0.50    0.93    --  -70.00 -68.00 -40.80  176
 78  \w   -137.00 -48.00   0.50    0.93    --  -70.00 -73.00  98.29  178
 79  \w   -138.00 -50.00   0.50    0.93    --  -70.00 -68.00 -63.78  176
;
_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      -0.0037667000
_diffrn_orient_matrix_UB_12      -0.0005325000
_diffrn_orient_matrix_UB_13      -0.0645488000
_diffrn_orient_matrix_UB_21      -0.0119067000
_diffrn_orient_matrix_UB_22      -0.1493105000
_diffrn_orient_matrix_UB_23      0.0002937000
_diffrn_orient_matrix_UB_31      -0.1800729000
_diffrn_orient_matrix_UB_32      0.0098087000
_diffrn_orient_matrix_UB_33      0.0013123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            69572
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.370
_diffrn_reflns_theta_min         3.705
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.984
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.798
_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    1.427
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.134
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2274
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0721P)^2^+0.7269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2123
_reflns_number_total             2274
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09987a2.cif
_cod_data_source_block           w200518_1_1
_cod_database_code               7122851
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C11H12FNO3
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.93 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C5(H5)
3.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              13835
_olex2_date_sample_submission    2018-05-17
_olex2_submission_original_sample_id w200518_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 1.951
_oxdiff_exptl_absorpt_empirical_full_min 0.594