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_4030989
_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 H22 N2 O S'
_chemical_formula_sum            'C19 H22 N2 O S'
_chemical_formula_weight         326.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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
_audit_creation_date             2014-11-07
_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            4
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_cell_length_b                   6.3820(2)
_cell_length_c                   19.0726(6)
_cell_measurement_reflns_used    7071
_cell_measurement_temperature    120.00(10)
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_cell_measurement_theta_min      4.7770
_cell_volume                     1678.22(9)
_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)'
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_diffrn_ambient_environment      N~2~
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_diffrn_detector_area_resol_mean 5.3073
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_diffrn_measurement_details
;
  1 omega  -38.00   33.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -      -40.8054   38.0000 -150.0000 71

  2 omega  -81.00   39.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -      -40.8054   19.0000  150.0000 120

  3 omega   23.00   61.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -       40.8054   77.0000  -30.0000 38

  4 omega   18.00   73.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -       40.8054   38.0000   90.0000 55

  5 omega   21.00   57.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -       40.8054   57.0000  120.0000 36

  6 omega   62.00   96.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -       40.8054 -125.0000   30.0000 34

  7 omega   44.00   72.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -       40.8054   38.0000 -120.0000 28

  8 omega   13.00   41.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -       40.8054   77.0000   90.0000 28

  9 omega   13.00   91.00   1.0000    5.1500
omega____ theta____ kappa____ phi______ frames
    -       40.8054   77.0000  150.0000 78

 10 omega   77.00  103.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   63.0000 -150.0601 26

 11 omega   95.00  176.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310  125.0000 -120.0000 81

 12 omega   74.00  100.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000 -180.0000 26

 13 omega   78.00  105.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  120.0000 27

 14 omega  142.00  169.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  120.0000 27

 15 omega   80.00  106.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   54.0000 -158.9311 26

 16 omega   79.00  110.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   58.0000   47.9300 31

 17 omega   78.00  104.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000  150.0000 26

 18 omega   74.00  100.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  120.0000 26

 19 omega  113.00  177.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  150.0000 64

 20 omega   77.00  176.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   62.0000   94.8770 99

 21 omega   78.00  104.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   60.0000 26

 22 omega   74.00  100.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000   90.0000 26

 23 omega   74.00  100.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000  150.0000 26

 24 omega   74.00  101.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000   60.0000 27

 25 omega   24.00   99.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -94.0000 -180.0000 75

 26 omega   82.00  107.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000   90.0000 25

 27 omega   78.00  105.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000 -180.0000 27

 28 omega   79.00  104.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   90.0000 25

 29 omega  107.00  134.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   61.0000   90.0000 27

 30 omega   77.00  104.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000 -150.0000 27

 31 omega   71.00  101.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -94.0000   60.0000 30

 32 omega  114.00  175.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   77.0000 -150.0000 61

 33 omega   26.00   66.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -94.0000   60.0000 40

 34 omega  142.00  169.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   58.0000   47.9300 27

 35 omega   82.00  109.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000 -180.0000 27

 36 omega   81.00  138.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   45.0000  150.0000 57

 37 omega  125.00  152.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   55.0000 -168.2354 27

 38 omega   81.00  106.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   30.0000   90.0000 25

 39 omega   80.00  105.00   1.0000   20.5900
omega____ theta____ kappa____ phi______ frames
    -      106.6310   55.0000 -168.2354 25
;
_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      -0.0565483000
_diffrn_orient_matrix_UB_12      -0.0238523000
_diffrn_orient_matrix_UB_13      -0.0798120000
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_diffrn_orient_matrix_UB_22      0.0217376000
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_diffrn_orient_matrix_UB_31      0.0031138000
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_diffrn_orient_matrix_UB_33      -0.0099638000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
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_diffrn_reflns_limit_k_min       -7
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_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14891
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_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.886
_diffrn_reflns_theta_min         3.205
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
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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
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_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.046
_refine_diff_density_max         4.499
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_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    constr
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_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.1146
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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^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2766
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_reflns_number_gt                2977
_reflns_number_total             3362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00048_si_002.cif
_cod_data_source_block           compound_7c
_cod_depositor_comments
'Adding full bibliography for 4030982--4030996.cif.'
_cod_original_cell_volume        1678.23(9)
_cod_database_code               4030989
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C19 H22 N2 O1 S1'
_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:
 C15(H15), C9(H9), C13(H13), C18(H18), C16(H16), C11(H11), C19(H19), C10(H10),
 C12(H12), C17(H17)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              38239
_shelx_hkl_checksum              49879
_olex2_submission_special_instructions 'No special instructions were received'