The Anancomeric Character of the Pharmacophore 1,3,4-Thiadiazoline Framework in Chiral Spiro-Cyclohexyl Derivatives: Effects on Stereochemistry and Spiro-Junction Lability. Thermodynamic Aspects.
Menta, Sergio; Carradori, Simone; Secci, Daniela; Faggi, Cristina; Mannina, Luisa; Cirilli, Roberto; Pierini, Marco; The Journal of organic chemistry 80 (2015) 11932–11940; doi:10.1021/acs.joc.5b01635

data_4031755
_publ_section_title
;
 The Anancomeric Character of the Pharmacophore 1,3,4-Thiadiazoline
 Framework in Chiral Spiro-Cyclohexyl Derivatives: Effects on
 Stereochemistry and Spiro-Junction Lability. Thermodynamic Aspects.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11932
_journal_page_last               11940
_journal_paper_doi               10.1021/acs.joc.5b01635
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H25 N3 O2 S'
_chemical_formula_sum            'C15 H25 N3 O2 S'
_chemical_formula_weight         311.44
_chemical_name_systematic
;(5R,6S)-(+)-N-(6-tert-butyl-1-formyl-4-thia-1,2-
diazaspiro[4.5]dec-2-en-3-yl)acetamide
;
_space_group_IT_number           19
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_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_atom_sites_solution_hydrogens   geom
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_audit_creation_date
;
'Thu May 10 11:18:32 2012'
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_cell_length_c                   17.1490(10)
_cell_measurement_reflns_used    4476
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_cell_volume                     1674.4(3)
_computing_cell_refinement
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
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_computing_data_collection
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
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CrysAlisPro, Oxford Diffraction Ltd.,
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(compiled Oct 25 2010,18:11:34)
;
_computing_molecular_graphics    Ortep3
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_diffrn_ambient_temperature      293(2)
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_diffrn_measurement_details
;
  1 omega  -91.00    3.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.4074  125.0000   60.0000 94

  2 omega -116.00  -83.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -46.4074 -125.0000  150.0000 33

  3 omega   73.00   98.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       46.4074  125.0000  -30.0000 25

  4 omega -165.00  -95.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -      -90.0000  -91.0000   82.0000 70

  5 omega   33.00   74.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       97.9419  -45.0000 -150.0000 41

  6 omega   35.00   69.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       97.9419  -45.0000  -30.0000 34

  7 omega   48.00  133.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       97.9419  -15.0000 -180.0000 85

  8 omega   41.00   77.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       97.9419  -45.0000   60.0000 36

  9 omega   35.00   64.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       97.9419  -45.0000  -60.0000 29

 10 omega   75.00  153.00   1.0000    2.5000
omega____ theta____ kappa____ phi______ frames
    -       97.9419   45.0000 -180.0000 78
;
_diffrn_measurement_device_type  'Xcalibur, Onyx'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
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_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0276
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_diffrn_reflns_theta_max         71.23
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_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        50
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.783
_exptl_absorpt_correction_T_max  0.9479
_exptl_absorpt_correction_T_min  0.8827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             672
_exptl_crystal_recrystallization_method acetone-water
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.012(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0505P)^2^+0.2681P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0945
_reflns_number_gt                2723
_reflns_number_total             3087
_reflns_threshold_expression     >2sigma(I)
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_cod_depositor_comments
'Adding full bibliography for 4031753--4031756.cif.'
_cod_database_code               4031755