Activation and regioselectivity of five-membered cyclic thionocarbamates to nucleophilic attack
Awheda, Ismail; Saygili, Nezire; Garner, A. Christopher; Wallis, John D.; RSC Advances 3 (2013) 24997–; doi:10.1039/c3ra41074a

data_7239009
_publ_section_title
;
 Activation and regioselectivity of five-membered cyclic thionocarbamates
 to nucleophilic attack
;
_journal_issue                   47
_journal_name_full               'RSC Advances'
_journal_page_first              24997
_journal_paper_doi               10.1039/c3ra41074a
_journal_volume                  3
_journal_year                    2013
_chemical_formula_sum            'C9 H15 N O3 S'
_chemical_formula_weight         217.28
_chemical_name_systematic
;
3-Butoxycarbonyl-4-methylthiazolidin-2-one,
compound 31
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 100.177(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6972(6)
_cell_length_b                   6.7661(3)
_cell_length_c                   17.4884(10)
_cell_measurement_reflns_used    2312
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.2793
_cell_measurement_theta_min      3.0046
_cell_volume                     1129.40(11)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 15.9832
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4666
_diffrn_reflns_theta_full        26.75
_diffrn_reflns_theta_max         27.34
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Aug 2 2010,13:00:58)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.3627
_exptl_crystal_size_mid          0.2459
_exptl_crystal_size_min          0.1817
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0516
_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^)+(0.0506P)^2^+1.1988P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1271
_reflns_number_gt                1996
_reflns_number_total             2390
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra41074a.txt
_cod_data_source_block           compound31
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7239009