Effects of thionation and fluorination on cis-trans isomerization in tertiary amides: an investigation of N-alkylglycine (peptoid) rotamers.
Engel-Andreasen, Jens; Wich, Kathrine; Laursen, Jonas S.; Harris, Pernille; Olsen, Christian A.; The Journal of organic chemistry 80 (2015) 5415–5427; doi:10.1021/acs.joc.5b00048

data_4030992
_publ_section_title
;
 Effects of thionation and fluorination on cis-trans isomerization in
 tertiary amides: an investigation of N-alkylglycine (peptoid) rotamers.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5415
_journal_page_last               5427
_journal_paper_doi               10.1021/acs.joc.5b00048
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C19 H20 F2 N2 O2'
_chemical_formula_sum            'C19 H20 F2 N2 O2'
_chemical_formula_weight         346.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-26
_audit_creation_method
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.36582(11)
_cell_length_b                   15.33727(14)
_cell_length_c                   9.60241(9)
_cell_measurement_reflns_used    7960
_cell_measurement_temperature    119.97(10)
_cell_measurement_theta_max      76.4010
_cell_measurement_theta_min      4.5580
_cell_volume                     1673.90(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.97(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3073
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details
;
  1 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0554   38.0000   60.0000 83

  2 omega    8.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0554   77.0000   90.0000 109

  3 omega   23.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.0554 -125.0000   60.0000 74

  4 omega   39.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 60

  5 omega   39.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 60

  6 omega   36.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 80

  7 omega   86.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 92

  8 omega   36.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 55

  9 omega   39.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -30.0000 60

 10 omega -114.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0554  -57.0000  -60.0000 101

 11 omega -114.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0554  -57.0000 -180.0000 101

 12 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0554   38.0000 -120.0000 83

 13 omega   84.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000   60.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0412701000
_diffrn_orient_matrix_UB_12      -0.0934412000
_diffrn_orient_matrix_UB_13      -0.0330612000
_diffrn_orient_matrix_UB_21      0.0446768000
_diffrn_orient_matrix_UB_22      -0.0307114000
_diffrn_orient_matrix_UB_23      0.1433247000
_diffrn_orient_matrix_UB_31      -0.1210838000
_diffrn_orient_matrix_UB_32      0.0204922000
_diffrn_orient_matrix_UB_33      0.0640908000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8692
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.598
_diffrn_reflns_theta_min         4.843
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_description       irregular
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.605
_exptl_crystal_size_mid          0.376
_exptl_crystal_size_min          0.233
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1320 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0301
_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^)+(0.0519P)^2^+0.3026P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0799
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_full    0.876
_reflns_Friedel_fraction_max     0.818
_reflns_number_gt                3122
_reflns_number_total             3164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00048_si_002.cif
_cod_data_source_block           compound_10
_cod_depositor_comments
'Adding full bibliography for 4030982--4030996.cif.'
_cod_database_code               4030992
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C19 H20 F2 N2 O2'
_reflns_odcompleteness_completeness 98.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C11(H11), C19(H19), C17(H17), C13(H13), C12(H12), C15(H15),
 C10(H10), C9(H9), C16(H16)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              78674
_shelx_hkl_checksum              55145
_olex2_submission_special_instructions 'No special instructions were received'