Stereoselective synthesis of 4-aminobenzo[c][1,2]thiazine via a modification of the Harmata benzothiazine synthesis
Battula, Sivarama Krishna; G. V., Subbareddy; I. E., Chakravarthy; Saravanan, Vadivelu; RSC Adv.  (2016) –; doi:10.1039/C6RA08590C

data_7225394
_publ_section_title
;
 Stereoselective synthesis of 4-aminobenzo[c][1,2]thiazine via a
 modification of the Harmata benzothiazine synthesis
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA08590C
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_sum            'C14 H14 N2 O S'
_chemical_formula_weight         258.31
_chemical_melting_point          408.6(5)
_chemical_name_systematic
'(2S,4S)-4-amino-2-phenyl-3,4-dihydrobenzo[c][1,2]thiazine 2-oxide'
_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
_audit_update_record
;
2016-03-30 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4373(6)
_cell_length_b                   9.4766(6)
_cell_length_c                   17.5593(15)
_cell_measurement_reflns_used    2311
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.4
_cell_volume                     1237.59(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6041
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.44
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_T_max  0.5
_exptl_absorpt_correction_T_min  0.2
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0311
_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^)+(0.0435P)^2^+0.2859P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0780
_reflns_number_gt                2238
_reflns_number_total             2311
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ra08590c2.cif
_cod_data_source_block           red
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '408.15-409.15' was changed to
'408.6(5)' - the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 
;
_cod_original_cell_volume        1237.58(17)
_cod_database_code               7225394
_solvent_exptl_crystal_recrystallization_method Ethanol