# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_red
_database_code_depnum_ccdc_archive 'CCDC 1420064'
_audit_update_record             
;
2016-03-30 deposited with the CCDC.
2016-05-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'(2S,4S)-4-amino-2-phenyl-3,4-dihydrobenzo[c][1,2]thiazine 2-oxide'
_chemical_name_common            ?
_chemical_melting_point          408.15-409.15
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O S'
_chemical_formula_weight         258.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_chemical_absolute_configuration rmad
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.4373(6)
_cell_length_b                   9.4766(6)
_cell_length_c                   17.5593(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1237.58(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2311
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      26.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             516
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2
_exptl_absorpt_correction_T_max  0.5
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6041
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.44
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2311
_reflns_number_gt                2238
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.2859P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.11(7)
_refine_ls_number_reflns         2311
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S001 S 0.83712(6) 0.07638(4) 0.66724(3) 0.01849(13) Uani 1 1 d . . .
O002 O 0.79461(18) -0.07350(13) 0.66991(8) 0.0251(3) Uani 1 1 d . . .
N003 N 0.7135(2) 0.18423(18) 0.70548(9) 0.0230(4) Uani 1 1 d . . .
N004 N 1.2020(2) 0.08668(19) 0.83574(10) 0.0260(4) Uani 1 1 d . . .
C005 C 0.8398(3) 0.27205(19) 0.55250(12) 0.0239(4) Uani 1 1 d . . .
C006 C 0.8871(2) 0.16634(18) 0.82770(11) 0.0192(4) Uani 1 1 d . . .
C007 C 1.0326(2) 0.0716(2) 0.79438(11) 0.0198(4) Uani 1 1 d . . .
C008 C 0.8940(3) 0.0654(2) 0.44148(12) 0.0267(4) Uani 1 1 d . . .
C009 C 0.8766(3) 0.02600(19) 0.51708(11) 0.0223(4) Uani 1 1 d . . .
C010 C 0.7397(3) 0.21170(18) 0.78398(11) 0.0191(4) Uani 1 1 d . . .
C011 C 0.8508(3) 0.12936(19) 0.57161(11) 0.0197(4) Uani 1 1 d . . .
C012 C 0.8958(3) 0.2070(2) 0.90381(11) 0.0236(4) Uani 1 1 d . . .
C013 C 0.6054(3) 0.29398(18) 0.81843(11) 0.0206(4) Uani 1 1 d . . .
C014 C 0.6162(3) 0.3308(2) 0.89457(12) 0.0236(4) Uani 1 1 d . . .
C015 C 1.0546(3) 0.09707(19) 0.70834(11) 0.0197(4) Uani 1 1 d . . .
C016 C 0.7632(3) 0.2890(2) 0.93735(12) 0.0260(4) Uani 1 1 d . . .
C017 C 0.8838(3) 0.2063(2) 0.42139(12) 0.0289(5) Uani 1 1 d . . .
C018 C 0.8550(3) 0.3085(2) 0.47653(12) 0.0301(5) Uani 1 1 d . . .
H1 H 0.823(3) 0.337(2) 0.5896(12) 0.020(5) Uiso 1 1 d . . .
H3 H 0.920(3) -0.009(3) 0.4002(13) 0.038(6) Uiso 1 1 d . . .
H2 H 0.882(3) -0.074(2) 0.5337(12) 0.024(5) Uiso 1 1 d . . .
H5 H 0.994(3) 0.176(2) 0.9306(13) 0.026(6) Uiso 1 1 d . . .
H4 H 0.497(3) 0.324(2) 0.7896(13) 0.025(6) Uiso 1 1 d . . .
H6 H 0.767(3) 0.318(2) 0.9901(13) 0.025(6) Uiso 1 1 d . . .
H7 H 1.247(3) 0.174(3) 0.8302(13) 0.036(6) Uiso 1 1 d . . .
H8 H 1.288(3) 0.036(2) 0.8152(13) 0.032(7) Uiso 1 1 d . . .
H16 H 0.849(4) 0.409(3) 0.4621(14) 0.047(7) Uiso 1 1 d . . .
H15 H 0.896(3) 0.235(2) 0.3668(13) 0.030(6) Uiso 1 1 d . . .
H30 H 0.526(3) 0.383(2) 0.9171(13) 0.026(6) Uiso 1 1 d . . .
H35 H 1.089(3) 0.193(2) 0.6977(13) 0.028(6) Uiso 1 1 d . . .
H36 H 1.138(3) 0.026(2) 0.6841(11) 0.023(5) Uiso 1 1 d . . .
H37 H 0.995(2) -0.025(2) 0.8022(11) 0.012(5) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S001 O002 1.4559(13) . ?
S001 N003 1.5299(16) . ?
S001 C011 1.7557(19) . ?
S001 C015 1.7819(19) . ?
N003 C010 1.416(2) . ?
N004 C007 1.461(2) . ?
N004 H7 0.90(3) . ?
N004 H8 0.88(2) . ?
C005 C018 1.383(3) . ?
C005 C011 1.396(3) . ?
C005 H1 0.91(2) . ?
C006 C012 1.393(3) . ?
C006 C010 1.406(3) . ?
C006 C007 1.523(3) . ?
C007 C015 1.539(3) . ?
C007 H37 0.965(19) . ?
C008 C017 1.384(3) . ?
C008 C009 1.385(3) . ?
C008 H3 1.03(2) . ?
C009 C011 1.383(3) . ?
C009 H2 0.99(2) . ?
C010 C013 1.404(3) . ?
C012 C016 1.386(3) . ?
C012 H5 0.92(2) . ?
C013 C014 1.384(3) . ?
C013 H4 0.99(2) . ?
C014 C016 1.384(3) . ?
C014 H30 0.92(2) . ?
C015 H35 0.96(2) . ?
C015 H36 1.01(2) . ?
C016 H6 0.97(2) . ?
C017 C018 1.386(3) . ?
C017 H15 1.00(2) . ?
C018 H16 0.98(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O002 S001 N003 120.47(9) . . ?
O002 S001 C011 108.81(9) . . ?
N003 S001 C011 105.29(9) . . ?
O002 S001 C015 106.94(8) . . ?
N003 S001 C015 107.11(9) . . ?
C011 S001 C015 107.65(10) . . ?
C010 N003 S001 117.86(13) . . ?
C007 N004 H7 110.9(16) . . ?
C007 N004 H8 111.7(15) . . ?
H7 N004 H8 101(2) . . ?
C018 C005 C011 117.98(19) . . ?
C018 C005 H1 122.2(13) . . ?
C011 C005 H1 119.8(13) . . ?
C012 C006 C010 118.38(17) . . ?
C012 C006 C007 119.95(17) . . ?
C010 C006 C007 121.65(17) . . ?
N004 C007 C006 111.33(16) . . ?
N004 C007 C015 112.41(16) . . ?
C006 C007 C015 111.09(15) . . ?
N004 C007 H37 105.9(11) . . ?
C006 C007 H37 107.2(11) . . ?
C015 C007 H37 108.6(11) . . ?
C017 C008 C009 119.9(2) . . ?
C017 C008 H3 119.6(13) . . ?
C009 C008 H3 120.4(13) . . ?
C011 C009 C008 119.05(18) . . ?
C011 C009 H2 118.7(12) . . ?
C008 C009 H2 122.3(12) . . ?
C013 C010 C006 119.30(17) . . ?
C013 C010 N003 115.06(17) . . ?
C006 C010 N003 125.62(17) . . ?
C009 C011 C005 121.87(18) . . ?
C009 C011 S001 117.88(14) . . ?
C005 C011 S001 120.24(15) . . ?
C016 C012 C006 122.01(19) . . ?
C016 C012 H5 121.9(14) . . ?
C006 C012 H5 116.1(14) . . ?
C014 C013 C010 120.98(18) . . ?
C014 C013 H4 117.9(13) . . ?
C010 C013 H4 121.0(13) . . ?
C013 C014 C016 119.86(19) . . ?
C013 C014 H30 120.4(15) . . ?
C016 C014 H30 119.7(15) . . ?
C007 C015 S001 106.50(13) . . ?
C007 C015 H35 111.6(14) . . ?
S001 C015 H35 105.5(14) . . ?
C007 C015 H36 112.1(11) . . ?
S001 C015 H36 108.3(12) . . ?
H35 C015 H36 112.4(18) . . ?
C014 C016 C012 119.44(19) . . ?
C014 C016 H6 117.4(13) . . ?
C012 C016 H6 123.1(13) . . ?
C008 C017 C018 120.32(19) . . ?
C008 C017 H15 120.1(12) . . ?
C018 C017 H15 119.6(12) . . ?
C005 C018 C017 120.81(19) . . ?
C005 C018 H16 119.1(15) . . ?
C017 C018 H16 120.1(15) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.042
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Ethanol
