Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines, via an unprecedented intramolecular electrophilic aromatic substitution.
Mercey, Guillaume; Legay, Remi; Lohier, Jean-François; Santos, Jana Sopkova-de Oliveira; Levillain, Jocelyne; Gaumont, Annie-Claude; Gulea, Mihaela; Organic & biomolecular chemistry 8 (2010) 2520–2521; doi:10.1039/c003050c

data_7153353
_publ_section_title
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 Synthesis of 3-amino-thiochromanes from 4-benzyl 2-thiazolines, via an
 unprecedented intramolecular electrophilic aromatic substitution.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2520
_journal_page_last               2521
_journal_paper_doi               10.1039/c003050c
_journal_volume                  8
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C9 H12 N S, Cl'
_chemical_formula_sum            'C9 H12 Cl N S'
_chemical_formula_weight         201.71
_chemical_melting_point          487
_chemical_name_systematic
;
(S)-3-Aminothiochromane hydrochloride
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.3668(11)
_cell_length_b                   6.2152(12)
_cell_length_c                   29.035(6)
_cell_measurement_reflns_used    5571
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.80
_cell_volume                     968.5(3)
_computing_cell_refinement       'APEX2 software'
_computing_data_collection       'APEX2 software (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'Mercury (Macrae <i>et al.</i>, 2006)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0690
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15838
_diffrn_reflns_theta_full        30.34
_diffrn_reflns_theta_max         30.34
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.554
_exptl_absorpt_correction_T_max  0.9718
_exptl_absorpt_correction_T_min  0.7235
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   (SAINT)
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 'Flack H D (1983), 1157 Friedel pairs'
_refine_ls_abs_structure_Flack   0.11(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         2871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0590
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0619P)^2^+0.5533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1406
_reflns_number_gt                2343
_reflns_number_total             2871
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c003050c.txt
_cod_data_source_block           (S)-3a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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)2(1)2(1) '
_cod_database_code               7153353