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_4030990
_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 O S'
_chemical_formula_sum            'C14 H17 F3 N2 O S'
_chemical_formula_weight         318.35
_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             2014-10-10
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Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
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_cell_length_c                   27.6640(5)
_cell_measurement_reflns_used    9069
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      73.8790
_cell_measurement_theta_min      3.1970
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_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
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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)
;
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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)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
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;
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omega____ theta____ kappa____ phi______ frames
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  2 omega   23.00   63.00   1.0000    1.1200
omega____ theta____ kappa____ phi______ frames
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  3 omega   23.00   50.00   1.0000    1.1200
omega____ theta____ kappa____ phi______ frames
    -       41.0554   77.0000   60.0000 27

  4 omega   10.00   97.00   1.0000    1.1200
omega____ theta____ kappa____ phi______ frames
    -       41.0554   77.0000   30.0000 87

  5 omega   81.00  108.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
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  6 omega  130.00  178.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
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  7 omega  153.00  178.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
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  8 omega  131.00  178.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
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  9 omega  138.00  164.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000   60.0000 26

 10 omega  106.00  167.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   30.0000 61

 11 omega   83.00  110.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000  -30.0000 27

 12 omega   83.00  177.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000  -60.0000 94

 13 omega   79.00  104.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   57.0000   17.2745 25

 14 omega   78.00  104.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   60.0000 26

 15 omega   79.00  104.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   30.0000 25

 16 omega   78.00  105.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000    0.0000 27

 17 omega   78.00  104.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  -30.0000 26

 18 omega   78.00  104.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  -60.0000 26

 19 omega   77.00  102.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   69.0000  -63.5502 25

 20 omega   74.00  178.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  -30.0000 104

 21 omega   81.00  169.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000   60.0000 88

 22 omega   75.00  100.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   75.0000   53.0517 25

 23 omega   74.00  100.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000   30.0000 26

 24 omega   75.00  102.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000    0.0000 27

 25 omega   74.00  100.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  -60.0000 26

 26 omega   75.00  100.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   76.0000  -92.0371 25

 27 omega   34.00   62.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -30.0000  -60.0000 28

 28 omega   34.00   95.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -45.0000  -90.0000 61

 29 omega   35.00   92.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -45.0000    0.0000 57

 30 omega   34.00   84.00   1.0000    1.1200
omega____ theta____ kappa____ phi______ frames
    -       41.0554 -125.0000  -30.0000 50

 31 omega   32.00  106.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -94.0000   30.0000 74

 32 omega   75.00  100.00   1.0000    4.4850
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000   60.0000 25

 33 omega -128.00   47.00   1.0000    1.1200
omega____ theta____ kappa____ phi______ frames
    -      -41.0554    0.0000   60.0000 175
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
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_diffrn_orient_matrix_UB_11      0.0694993000
_diffrn_orient_matrix_UB_12      -0.1303129000
_diffrn_orient_matrix_UB_13      -0.0312117000
_diffrn_orient_matrix_UB_21      0.0004088000
_diffrn_orient_matrix_UB_22      0.0961112000
_diffrn_orient_matrix_UB_23      -0.0453693000
_diffrn_orient_matrix_UB_31      0.2571977000
_diffrn_orient_matrix_UB_32      0.0349311000
_diffrn_orient_matrix_UB_33      0.0085148000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
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_diffrn_reflns_limit_h_max       7
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_diffrn_reflns_limit_k_min       -10
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_diffrn_reflns_number            13517
_diffrn_reflns_point_group_measured_fraction_full 1.000
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.146
_diffrn_reflns_theta_min         3.195
_diffrn_source                   'sealed X-ray tube'
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_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  1.00000
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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_colour            colourless
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.084
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;
 Flack x determined using 1156 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.004(16)
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_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0474
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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^)+(0.1009P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1238
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_cod_data_source_file            jo5b00048_si_002.cif
_cod_data_source_block           compound_8a
_cod_depositor_comments
'Adding full bibliography for 4030982--4030996.cif.'
_cod_original_cell_volume        1486.78(5)
_cod_database_code               4030990
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C14 H17 F3 N2 O1 S1'
_reflns_odcompleteness_completeness 99.94
_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:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C), C8(H8A,H8B,H8C)
;
_shelx_res_checksum              78335
_shelx_hkl_checksum              78082
_olex2_submission_special_instructions 'No special instructions were received'