The preferred conformation of N-β-fluoroethylamides. Observation of the fluorine amide gauche effect
O’Hagan, David; Bilton, Clair; Howard, Judith A. K.; Knight, Lee; Tozer, David J.; Journal of the Chemical Society, Perkin Transactions 2  (2000) 605–; doi:10.1039/b000205o

data_7213255
_publ_contact_author             'Dr. David O'Hagan'
_publ_section_title
;
 The preferred conformation of N-\b-fluoroethylamides. Observation of the
 fluorine amide gauche effect
;
_journal_issue                   4
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              605
_journal_paper_doi               10.1039/b000205o
_journal_year                    2000
_chemical_formula_sum            'C9 H8 F N3 O5'
_chemical_formula_weight         257.18
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.60(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.114(2)
_cell_length_b                   4.824(1)
_cell_length_c                   20.996(4)
_cell_measurement_reflns_used    996
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.44
_cell_measurement_theta_min      10.13
_cell_volume                     1022.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 'not relevant'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6836
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.149
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996??'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.671
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0448P)^2^+0.4786P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0969
_reflns_number_gt                1875
_reflns_number_total             2331
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b000205osup1.cif
_cod_data_source_block           00srv092
_cod_original_cell_volume        1022.3(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7213255