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_4030986
_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         'C18 H22 N2 O S'
_chemical_formula_sum            'C18 H22 N2 O S'
_chemical_formula_weight         314.43
_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             2014-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4866)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.42849(13)
_cell_length_b                   10.19836(14)
_cell_length_c                   17.3158(3)
_cell_measurement_reflns_used    4609
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      73.6310
_cell_measurement_theta_min      5.0230
_cell_volume                     1665.00(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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      120.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3073
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details
;
  1 omega   -9.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0554   38.0000  -90.0000 26

  2 omega  -80.00  -13.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0554  125.0000  120.0000 67

  3 omega -115.00  -24.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0554  -38.0000  -30.0000 91

  4 omega   51.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -30.0000 -180.0000 40

  5 omega   31.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -30.0000  -60.0000 59

  6 omega   31.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -30.0000 -120.0000 59

  7 omega   58.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -30.0000   60.0000 33

  8 omega   24.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  -95.0000  120.0000 84

  9 omega   94.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  125.0000 -180.0000 81

 10 omega  125.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      106.6310  125.0000  -60.0000 32
;
_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      -0.0975129000
_diffrn_orient_matrix_UB_12      -0.0170105000
_diffrn_orient_matrix_UB_13      0.0706634000
_diffrn_orient_matrix_UB_21      0.1292092000
_diffrn_orient_matrix_UB_22      0.0136604000
_diffrn_orient_matrix_UB_23      0.0538898000
_diffrn_orient_matrix_UB_31      -0.0228242000
_diffrn_orient_matrix_UB_32      0.1494919000
_diffrn_orient_matrix_UB_33      0.0029001000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5913
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.978
_diffrn_reflns_theta_min         5.033
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
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    1.254
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.010(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0587P)^2^+0.0232P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0908
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                3151
_reflns_number_total             3270
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b00048_si_002.cif
_cod_data_source_block           compound_5b
_cod_depositor_comments
'Adding full bibliography for 4030982--4030996.cif.'
_cod_database_code               4030986
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C18 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:
 C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C16(H16), C15(H15), C10(H10), C1(H16A), C18(H17)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C2(H2A,H2B,H2C), C8(H8A,H8B,H8C), C5(H1A,H1B,H1C)
;
_shelx_res_checksum              60450
_shelx_hkl_checksum              90315
_olex2_submission_special_instructions 'No special instructions were received'