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_7122849
_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_absolute_configuration ad
_chemical_formula_moiety         'C10 H12 F N O'
_chemical_formula_sum            'C10 H12 F N O'
_chemical_formula_weight         181.21
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-28
_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                101.380(3)
_cell_angle_beta                 93.123(3)
_cell_angle_gamma                94.168(3)
_cell_formula_units_Z            2
_cell_length_a                   5.7997(2)
_cell_length_b                   7.8020(3)
_cell_length_c                   10.7127(4)
_cell_measurement_reflns_used    5610
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      78.2460
_cell_measurement_theta_min      4.2490
_cell_volume                     472.78(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.958
_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    -59.00  31.00   0.50    1.24    --  -30.00  89.00 -72.35  180
  2  \w      5.00  32.00   0.50    1.24    --   34.00  88.00-131.48   54
  3  \w     27.00 115.00   0.50    1.24    --   46.00  67.00-107.09  176
  4  \w     98.00 178.00   0.50    4.95    --  110.00  38.00   0.00  160
  5  \w    149.00 176.00   0.50    4.95    --  110.00  77.00 -60.00   54
  6  \w    148.00 174.00   0.50    4.95    --  110.00  77.00   0.00   52
  7  \w    141.00 176.00   0.50    4.95    --  110.00  57.00  60.00   70
  8  \w    152.00 178.00   0.50    4.95    --  110.00  38.00  90.00   52
  9  \w    131.00 178.00   0.50    4.95    --  110.00  57.00 150.00   94
 10  \w    111.00 139.00   0.50    4.95    --  110.00  38.00 120.00   56
 11  \w    109.00 136.00   0.50    4.95    --  110.00  38.00  90.00   54
 12  \w    106.00 131.00   0.50    4.95    --  110.00  38.00 150.00   50
 13  \w    100.00 139.00   0.50    4.95    --  110.00  57.00  90.00   78
 14  \w     96.00 122.00   0.50    4.95    --  110.00  57.00  60.00   52
 15  \w     97.00 148.00   0.50    4.95    --  110.00  57.00 120.00  102
 16  \w     94.00 123.00   0.50    4.95    --  110.00 -19.00  30.00   58
 17  \w     98.00 129.00   0.50    4.95    --  110.00  38.00 -30.00   62
 18  \w     86.00 177.00   0.50    4.95    --  110.00  77.00  30.00  182
 19  \w    122.00 164.00   0.50    4.95    --  110.00  77.00-120.00   84
 20  \w    123.00 150.00   0.50    4.95    --  110.00  77.00-150.00   54
 21  \w    124.00 164.00   0.50    4.95    --  110.00  77.00-180.00   80
 22  \w     95.00 126.00   0.50    4.95    --  110.00  57.00-180.00   62
 23  \w     99.00 142.00   0.50    4.95    --  110.00  38.00-120.00   86
 24  \w    100.00 128.00   0.50    4.95    --  110.00  38.00-180.00   56
 25  \w     89.00 116.00   0.50    4.95    --  110.00  77.00-120.00   54
 26  \w     89.00 167.00   0.50    4.95    --  110.00  77.00 -90.00  156
 27  \w     96.00 130.00   0.50    4.95    --  110.00  57.00 -90.00   68
 28  \w     87.00 114.00   0.50    4.95    --  110.00  77.00-150.00   54
 29  \w     91.00 121.00   0.50    4.95    --  110.00  77.00-180.00   60
 30  \w     86.00 118.00   0.50    4.95    --  110.00  77.00 -60.00   64
 31  \w     91.00 118.00   0.50    4.95    --  110.00  77.00 -30.00   54
 32  \w     89.00 115.00   0.50    4.95    --  110.00  77.00   0.00   52
 33  \w     73.00 162.00   0.50    4.95    --   94.00  70.00  34.30  178
 34  \w     86.00 177.00   0.50    4.95    --  110.00  77.00 120.00  182
 35  \w     87.00 113.00   0.50    4.95    --  110.00  77.00  90.00   52
 36  \w     35.00 123.00   0.50    1.24    --   47.62  38.00  90.00  176
 37  \w     44.00  76.00   0.50    4.95    --  110.00 -57.00 150.00   64
 38  \w     51.00  82.00   0.50    4.95    --  110.00 -57.00  90.00   62
 39  \w     42.00 104.00   0.50    4.95    --  110.00 -99.00 120.00  124
 40  \w     46.00  82.00   0.50    4.95    --  110.00 -57.00   0.00   72
 41  \w     41.00  89.00   0.50    4.95    --  110.00 -99.00  30.00   96
 42  \w     84.00 120.00   0.50    4.95    --  110.00-125.00   0.00   72
 43  \w     80.00 119.00   0.50    4.95    --  110.00-125.00-120.00   78
 44  \w     52.00 130.00   0.50    4.95    --  110.00 -77.00-150.00  156
 45  \w     47.00  77.00   0.50    4.95    --  110.00-125.00-120.00   60
 46  \w     41.00  92.00   0.50    4.95    --  110.00 -99.00 -30.00  102
 47  \w     43.00  70.00   0.50    4.95    --  110.00 -57.00  30.00   54
 48  \w     46.00  73.00   0.50    4.95    --  110.00-125.00   0.00   54
 49  \w     35.00 123.00   0.50    1.24    --   47.62  38.00-180.00  176
 50  \w     25.00 113.00   0.50    1.24    --   46.00  72.00 -20.53  176
 51  \w     36.00 125.00   0.50    1.24    --   58.00  73.00  37.65  178
 52  \w     32.00 119.00   0.50    1.24    --   47.62  57.00 150.00  174
 53  \w     24.00 113.00   0.50    1.24    --   46.00  73.00 115.42  178
 54  \w      6.00  33.00   0.50    1.24    --   34.00  87.00   1.93   54
 55  \w      9.00  41.00   0.50    1.24    --   34.00  81.00 -87.53   64
 56  \w    -95.00  -9.00   0.50    4.95    --  -70.00 125.00  30.00  172
 57  \w   -141.00 -53.00   0.50    4.95    --  -70.00 -59.00 -48.13  176
 58  \w   -113.00 -78.00   0.50    1.24    --  -47.62 -77.00  60.00   70
 59  \w   -133.00 -44.00   0.50    4.95    --  -66.00 -73.00 154.88  178
 60  \w   -118.00 -38.00   0.50    1.24    --  -47.62-178.00  60.00  160
 61  \w   -127.00 -38.00   0.50    1.24    --  -58.00 -67.00-137.30  178
 62  \w   -140.00 -51.00   0.50    4.95    --  -70.00 -64.00 -83.36  178
 63  \w   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00  73.75  176
 64  \w   -139.00 -50.00   0.50    4.95    --  -70.00 -67.00  45.26  178
 65  \w   -138.00 -49.00   0.50    4.95    --  -70.00 -69.00-134.55  178
 66  \w   -140.00 -84.00   0.50    4.95    --  -70.00 -99.00-150.00  112
 67  \w   -139.00 -50.00   0.50    4.95    --  -70.00 -67.00 -90.68  178
 68  \w   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00  17.21  176
 69  \w   -140.00 -51.00   0.50    4.95    --  -70.00 -64.00-160.40  178
 70  \w   -140.00 -51.00   0.50    4.95    --  -70.00 -64.00 -61.00  178
 71  \w   -140.00 -84.00   0.50    4.95    --  -70.00 -99.00  60.00  112
 72  \w   -140.00 -53.00   0.50    4.95    --  -70.00 -61.00  88.70  174
 73  \w   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00  28.26  176
 74  \w   -139.00 -51.00   0.50    4.95    --  -70.00 -66.00 -11.30  176
 75  \w   -138.00 -50.00   0.50    4.95    --  -70.00 -68.00 152.37  176
 76  \w   -137.00 -49.00   0.50    4.95    --  -70.00 -71.00-172.31  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      -0.0284100000
_diffrn_orient_matrix_UB_12      -0.0452934000
_diffrn_orient_matrix_UB_13      -0.1469308000
_diffrn_orient_matrix_UB_21      -0.1495341000
_diffrn_orient_matrix_UB_22      -0.1694906000
_diffrn_orient_matrix_UB_23      0.0054316000
_diffrn_orient_matrix_UB_31      -0.2193616000
_diffrn_orient_matrix_UB_32      0.1004334000
_diffrn_orient_matrix_UB_33      0.0027271000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13622
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.974
_diffrn_reflns_theta_min         4.220
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.782
_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    1.273
_exptl_crystal_description       plate
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.083
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1292 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3651
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0406
_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^)+(0.0754P)^2^+0.0436P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1196
_reflns_Friedel_coverage         0.846
_reflns_Friedel_fraction_full    0.916
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                3115
_reflns_number_total             3651
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09987a2.cif
_cod_data_source_block           w230518_1_1
_cod_database_code               7122849
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C10H12FNO
_reflns_odcompleteness_completeness 99.94
_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
 N1B-H1B = N1A-H1A
 0.93 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2B(H2B)
3.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C4B(H4BA,H4BB)
3.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C6B(H6B), C7B(H7B),
 C8B(H8B), C9B(H9B), C10B(H10B)
3.d Idealised Me refined as rotating group:
 C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,H1BC)
;
_shelx_res_checksum              58355
_olex2_date_sample_data_collection 2018-05-23
_olex2_date_sample_submission    2018-05-23
_olex2_submission_original_sample_id w230518_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 1.858
_oxdiff_exptl_absorpt_empirical_full_min 0.667