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_4030994
_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 O S'
_chemical_formula_sum            'C19 H20 F2 N2 O S'
_chemical_formula_weight         362.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-25
_audit_creation_method
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Olex2 1.2
(compiled 2014.11.21 svn.r3092 for OlexSys, GUI svn.r4949)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.31801(6)
_cell_length_b                   10.65613(7)
_cell_length_c                   18.11473(12)
_cell_measurement_reflns_used    28236
_cell_measurement_temperature    120.3(6)
_cell_measurement_theta_max      73.8420
_cell_measurement_theta_min      2.4280
_cell_volume                     1798.68(2)
_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
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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)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
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_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -96.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8054  125.0000   30.0000 94

  2 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8054   38.0000   60.0000 83

  3 omega -114.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8054  -57.0000  -90.0000 101

  4 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8054  -99.0000  -90.0000 81

  5 omega   13.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8054   57.0000 -120.0000 101

  6 omega   79.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   55.0000 -160.0221 99

  7 omega   94.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  125.0000   90.0000 84

  8 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000 -150.0000 100

  9 omega   34.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -45.0000  150.0000 65

 10 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   30.0000  -90.0000 100

 11 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000 -120.0000 97

 12 omega   34.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -54.0000  -53.0000 77

 13 omega   30.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -30.0000  120.0000 61

 14 omega   34.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -45.0000 -150.0000 65

 15 omega   25.00  159.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -15.0000  150.0000 134

 16 omega   54.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   15.0000   90.0000 124

 17 omega   30.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -30.0000   60.0000 61

 18 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000 -180.0000 97

 19 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000 -150.0000 104

 20 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   30.0000 -180.0000 100

 21 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000 -180.0000 104

 22 omega   75.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   74.0000  160.7930 103

 23 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   30.0000 -120.0000 100

 24 omega   74.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  150.0000 104

 25 omega   78.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310   59.0000  155.9149 100

 26 omega -114.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8054  -57.0000  -30.0000 101

 27 omega -114.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8054  -68.0000  149.0000 104

 28 omega -117.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8054  -77.0000   60.0000 109

 29 omega    8.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8054   77.0000   90.0000 109

 30 omega    8.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8054   77.0000  -60.0000 109

 31 omega    8.00  117.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8054   77.0000    0.0000 109

 32 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8054  -99.0000 -180.0000 81

 33 omega   33.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310 -125.0000 -180.0000 89
;
_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      0.0787191000
_diffrn_orient_matrix_UB_12      -0.0892318000
_diffrn_orient_matrix_UB_13      -0.0533198000
_diffrn_orient_matrix_UB_21      -0.1433262000
_diffrn_orient_matrix_UB_22      -0.0303075000
_diffrn_orient_matrix_UB_23      -0.0383805000
_diffrn_orient_matrix_UB_31      0.0243196000
_diffrn_orient_matrix_UB_32      0.1096628000
_diffrn_orient_matrix_UB_33      -0.0539952000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.998
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_diffrn_reflns_limit_h_max       11
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33997
_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.996
_diffrn_reflns_theta_min         4.815
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56513
_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
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_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.173
_refine_diff_density_max         0.153
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;
 Flack x determined using 1529 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.002(4)
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         3644
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_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0240
_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^)+(0.0345P)^2^+0.3592P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0635
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_reflns_Friedel_fraction_max     0.994
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00048_si_002.cif
_cod_data_source_block           compound_12
_cod_depositor_comments
'Adding full bibliography for 4030982--4030996.cif.'
_cod_database_code               4030994
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C19 H20 F2 N2 O1 S1'
_reflns_odcompleteness_completeness 99.89
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C19(H19), C10(H10), C18(H18), C15(H15), C17(H17), C13(H13),
 C12(H12), C16(H16)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              34870
_shelx_hkl_checksum              26482
_olex2_submission_special_instructions 'No special instructions were received'