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_4030984
_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_absolute_configuration ad
_chemical_formula_moiety         'C14 H17 F3 N2 O2'
_chemical_formula_sum            'C14 H17 F3 N2 O2'
_chemical_formula_weight         302.29
_space_group_crystal_system      hexagonal
_space_group_IT_number           169
_space_group_name_Hall           'P 61'
_space_group_name_H-M_alt        'P 61'
_symmetry_space_group_name_Hall  'P 61'
_symmetry_space_group_name_H-M   'P 61'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
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_cell_formula_units_Z            6
_cell_length_a                   15.74885(18)
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_cell_length_c                   11.05787(17)
_cell_measurement_reflns_used    10125
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.0230
_cell_measurement_theta_min      3.2390
_cell_volume                     2375.20(5)
_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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;
  1 omega  -46.00   26.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -      -41.0554   38.0000 -180.0000 72

  2 omega  -91.00  -14.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
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  3 omega    9.00   34.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554   77.0000   30.0000 25

  4 omega   22.00   69.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554   19.0000   90.0000 47

  5 omega   19.00   46.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554   57.0000  -90.0000 27

  6 omega    9.00   64.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554   77.0000  -60.0000 55

  7 omega   80.00  114.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554   57.0000  -90.0000 34

  8 omega   27.00   54.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
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  9 omega   56.00   83.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554   77.0000   30.0000 27

 10 omega   24.00   85.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554 -125.0000  -90.0000 61

 11 omega   26.00   51.00   1.0000    9.4450
omega____ theta____ kappa____ phi______ frames
    -       41.0554   57.0000 -180.0000 25

 12 omega   78.00  105.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   90.0000 27

 13 omega   74.00  100.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000    0.0000 26

 14 omega   78.00  105.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   30.0000 27

 15 omega   78.00  105.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000    0.0000 27

 16 omega   79.00  106.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   60.0000 27

 17 omega   35.00   99.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -45.0000    0.0000 64

 18 omega   76.00  103.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  -30.0000 27

 19 omega   81.00  173.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000   90.0000 92

 20 omega   74.00  100.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000   60.0000 26

 21 omega   82.00  107.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000   30.0000 25

 22 omega   79.00  104.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  120.0000 25

 23 omega   82.00  119.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310 -127.0000    5.0000 37

 24 omega   82.00  109.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000    0.0000 27

 25 omega   79.00  119.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  -60.0000 40

 26 omega   79.00  104.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  -30.0000 25

 27 omega   84.00  111.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   30.0000   30.0000 27

 28 omega   83.00  110.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   30.0000   60.0000 27

 29 omega   74.00  101.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  -60.0000 27

 30 omega   75.00  101.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000   30.0000 26

 31 omega  123.00  177.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000    0.0000 54

 32 omega   84.00  162.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310  143.0000 -109.0000 78

 33 omega   76.00  103.00   1.0000   37.7850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   67.0000   34.6843 27
;
_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      -0.0254112000
_diffrn_orient_matrix_UB_12      0.0824864000
_diffrn_orient_matrix_UB_13      -0.0069461000
_diffrn_orient_matrix_UB_21      0.1100491000
_diffrn_orient_matrix_UB_22      0.0768759000
_diffrn_orient_matrix_UB_23      -0.0040278000
_diffrn_orient_matrix_UB_31      -0.0019303000
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_diffrn_orient_matrix_UB_33      -0.1390880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       19
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_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17686
_diffrn_reflns_point_group_measured_fraction_full 0.942
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.051
_diffrn_reflns_theta_min         3.240
_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_coefficient_mu    0.939
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_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_density_diffrn    1.268
_exptl_crystal_description       needle
_exptl_crystal_F_000             948
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_exptl_crystal_size_mid          0.065
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_refine_diff_density_min         -0.328
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_refine_ls_abs_structure_details
;
 Flack x determined using 1089 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(10)
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_refine_ls_R_factor_all          0.0816
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_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.1786P)^2^+0.3536P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2210
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_reflns_Friedel_fraction_max     0.859
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_cod_data_source_file            jo5b00048_si_002.cif
_cod_data_source_block           compound_4a
_cod_depositor_comments
'Adding full bibliography for 4030982--4030996.cif.'
_cod_original_cell_volume        2375.20(6)
_cod_database_code               4030984
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C14 H17 N2 O2 F3'
_reflns_odcompleteness_completeness 100.00
_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:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C11(H11), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              58710
_shelx_hkl_checksum              12811
_olex2_submission_special_instructions 'No special instructions were received'