Complementary regioselectivity in the synthesis of iminohydantoins: remarkable effect of amide substitution on the cyclization.
García-Valverde, María; Marcaccini, Stefano; González-Ortega, Alfonso; Rodríguez, Francisco Javier; Rojo, Josefa; Torroba, Tomás; Organic & biomolecular chemistry 11 (2013) 721–725; doi:10.1039/c2ob27098f

data_7152811
_publ_section_title
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 Complementary regioselectivity in the synthesis of iminohydantoins:
 remarkable effect of amide substitution on the cyclization.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              721
_journal_page_last               725
_journal_paper_doi               10.1039/c2ob27098f
_journal_volume                  11
_journal_year                    2013
_chemical_formula_moiety         'C13 H17 N3 O3 S'
_chemical_formula_sum            'C13 H17 N3 O3 S'
_chemical_formula_weight         295.36
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.807(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.939(3)
_cell_length_b                   5.4586(9)
_cell_length_c                   16.280(3)
_cell_measurement_reflns_used    2641
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.70
_cell_measurement_theta_min      2.52
_cell_volume                     1406.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13033
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.29
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.614130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS(SHELDRICK,2001)
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0475
_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^)+(0.0494P)^2^+0.6121P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1129
_refine_ls_wR_factor_ref         0.1280
_reflns_number_gt                1910
_reflns_number_total             2489
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob27098f.txt
_cod_data_source_block           datosm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7152811