Peptidyl-Prolyl Model Study: How Does the Electronic Effect Influence the Amide Bond Conformation?
Mykhailiuk, Pavel K.; Kubyshkin, Vladimir; Bach, Thorsten; Budisa, Nediljko; The Journal of organic chemistry 82 (2017) 8831–8841; doi:10.1021/acs.joc.7b00803

data_4032704
_publ_section_title
;
 Peptidyl-Prolyl Model Study: How Does the Electronic Effect Influence the
 Amide Bond Conformation?
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8831
_journal_page_last               8841
_journal_paper_doi               10.1021/acs.joc.7b00803
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C9 H12 F N O3'
_chemical_formula_weight         201.20
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_cell_angle_alpha                90.00
_cell_angle_beta                 95.4590(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.54257(9)
_cell_length_b                   12.11651(15)
_cell_length_c                   10.64996(13)
_cell_measurement_reflns_used    4629
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.5070
_cell_measurement_theta_min      3.6590
_cell_volume                     968.88(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0088
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5379
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         7.81
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.7969
_exptl_absorpt_correction_T_min  0.6986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0434P)^2^+0.3191P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0872
_reflns_number_gt                1653
_reflns_number_total             1709
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00803_si_002.cif
_cod_data_source_block           cu-1665
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4032704