# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_b1
_database_code_depnum_ccdc_archive 'CCDC 1050855'
_audit_update_record             
;
2015-02-23 deposited with the CCDC.
2015-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(4-Bromothenyl)(4-Methyl-4H-Benzo(b)(1,4)Thiazin-2-yl)Methanone
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Br N O S'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            red

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         346.24

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_int_tables_number      14
_chemical_absolute_configuration syn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7172(19)
_cell_length_b                   9.2242(17)
_cell_length_c                   13.153(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.150(16)
_cell_angle_gamma                90.00
_cell_volume                     1419.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1278
_cell_measurement_theta_min      3.2512
_cell_measurement_theta_max      28.9831
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.620
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    3.037
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.40655
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'CrysAlis Pro, Agilent Technologies'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5637
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_sigmaI/netI    0.0919
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         29.05
_reflns_number_total             3220
_reflns_number_gt                1872
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrysAlis Pro, Agilent Technologies'
_computing_cell_refinement       'CrysAlis Pro, Agilent Technologies'
_computing_data_reduction        'CrysAlis Pro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0544P)²+0.0000P] 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_number_reflns         3220
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1384
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.000
_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
Br Br 0.35903(4) -0.03638(6) 0.63035(4) 0.0540(2) Uani 1 1 d . . .
S1 S 1.09799(10) 0.13085(13) 0.66744(10) 0.0431(3) Uani 1 1 d . . .
O1 O 0.9302(3) -0.0444(3) 0.7530(3) 0.0503(9) Uani 1 1 d . . .
N1 N 0.9770(3) 0.2582(4) 0.4685(3) 0.0369(9) Uani 1 1 d . . .
C5 C 0.6854(4) 0.1338(5) 0.6467(3) 0.0377(12) Uani 1 1 d . . .
H005 H 0.7172 0.2261 0.6446 0.045 Uiso 1 1 calc R . .
C2 C 0.5898(4) -0.1404(5) 0.6499(4) 0.0417(12) Uani 1 1 d . . .
H006 H 0.5577 -0.2326 0.6497 0.050 Uiso 1 1 calc R . .
C15 C 1.3021(5) 0.4321(5) 0.5545(5) 0.0532(14) Uani 1 1 d . . .
H007 H 1.3735 0.4705 0.5737 0.064 Uiso 1 1 calc R . .
C7 C 0.8834(4) 0.0266(5) 0.6820(4) 0.0338(11) Uani 1 1 d . . .
C8 C 0.9532(4) 0.1194(5) 0.6223(3) 0.0329(11) Uani 1 1 d . . .
C10 C 1.0872(4) 0.3157(5) 0.4979(3) 0.0336(11) Uani 1 1 d . . .
C4 C 0.7575(4) 0.0144(5) 0.6603(3) 0.0323(11) Uani 1 1 d . . .
C9 C 0.9161(4) 0.1762(4) 0.5323(3) 0.0337(11) Uani 1 1 d . . .
H012 H 0.8405 0.1573 0.5114 0.040 Uiso 1 1 calc R . .
C11 C 1.1458(4) 0.2707(4) 0.5877(3) 0.0347(11) Uani 1 1 d . . .
C16 C 1.2506(4) 0.3333(5) 0.6159(4) 0.0450(13) Uani 1 1 d . . .
H014 H 1.2870 0.3079 0.6779 0.054 Uiso 1 1 calc R . .
C6 C 0.5690(4) 0.1190(5) 0.6362(3) 0.0374(11) Uani 1 1 d . . .
H015 H 0.5227 0.2005 0.6276 0.045 Uiso 1 1 calc R . .
C12 C 0.9213(4) 0.3039(5) 0.3714(3) 0.0470(13) Uani 1 1 d . . .
H01A H 0.9734 0.3616 0.3347 0.071 Uiso 1 1 calc R . .
H01B H 0.8546 0.3602 0.3840 0.071 Uiso 1 1 calc R . .
H01C H 0.8994 0.2200 0.3319 0.071 Uiso 1 1 calc R . .
C3 C 0.7065(4) -0.1220(5) 0.6616(4) 0.0411(12) Uani 1 1 d . . .
H017 H 0.7528 -0.2034 0.6705 0.049 Uiso 1 1 calc R . .
C14 C 1.2461(5) 0.4729(5) 0.4644(4) 0.0508(14) Uani 1 1 d . . .
H018 H 1.2804 0.5377 0.4214 0.061 Uiso 1 1 calc R . .
C13 C 1.1395(4) 0.4182(5) 0.4377(4) 0.0447(13) Uani 1 1 d . . .
H019 H 1.1013 0.4502 0.3780 0.054 Uiso 1 1 calc R . .
C1 C 0.5208(4) -0.0174(5) 0.6386(3) 0.0355(11) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br 0.0354(3) 0.0733(4) 0.0536(4) -0.0007(3) 0.0066(2) -0.0049(3)
S1 0.0334(7) 0.0530(8) 0.0429(8) 0.0155(6) 0.0020(6) -0.0001(6)
O1 0.044(2) 0.056(2) 0.051(2) 0.0249(18) 0.0021(18) 0.0014(17)
N1 0.038(2) 0.045(2) 0.028(2) 0.0028(19) 0.0063(18) -0.0005(19)
C5 0.039(3) 0.035(3) 0.040(3) 0.006(2) 0.010(2) -0.001(2)
C2 0.043(3) 0.036(3) 0.047(3) 0.000(2) 0.008(3) -0.009(2)
C15 0.041(3) 0.044(3) 0.075(4) -0.007(3) 0.010(3) -0.008(3)
C7 0.032(2) 0.034(3) 0.036(3) 0.000(2) 0.006(2) 0.007(2)
C8 0.029(2) 0.036(3) 0.034(3) 0.005(2) 0.005(2) 0.003(2)
C10 0.037(3) 0.031(2) 0.034(3) 0.001(2) 0.014(2) 0.004(2)
C4 0.034(2) 0.037(3) 0.026(2) 0.005(2) 0.007(2) -0.001(2)
C9 0.035(3) 0.034(2) 0.033(3) -0.003(2) 0.007(2) -0.003(2)
C11 0.033(3) 0.030(2) 0.042(3) 0.003(2) 0.006(2) 0.006(2)
C16 0.038(3) 0.046(3) 0.051(3) 0.005(3) 0.001(3) -0.001(2)
C6 0.040(3) 0.039(3) 0.034(3) 0.000(2) 0.007(2) 0.004(2)
C12 0.047(3) 0.062(3) 0.032(3) 0.010(3) 0.004(2) 0.003(3)
C3 0.044(3) 0.039(3) 0.041(3) 0.005(2) 0.009(2) 0.011(2)
C14 0.053(3) 0.035(3) 0.066(4) 0.006(3) 0.019(3) -0.005(3)
C13 0.059(4) 0.034(3) 0.043(3) 0.004(2) 0.016(3) 0.007(3)
C1 0.035(3) 0.046(3) 0.026(2) -0.001(2) 0.007(2) 0.001(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
Br C1 1.900(5) . ?
S1 C8 1.770(5) . ?
S1 C11 1.773(4) . ?
O1 C7 1.242(5) . ?
N1 C9 1.360(5) . ?
N1 C10 1.430(5) . ?
N1 C12 1.464(5) . ?
C5 C6 1.370(6) . ?
C5 C4 1.394(6) . ?
C5 H005 0.9300 . ?
C2 C3 1.379(6) . ?
C2 C1 1.397(6) . ?
C2 H006 0.9300 . ?
C15 C14 1.375(8) . ?
C15 C16 1.379(6) . ?
C15 H007 0.9300 . ?
C7 C8 1.446(6) . ?
C7 C4 1.491(6) . ?
C8 C9 1.344(6) . ?
C10 C11 1.396(6) . ?
C10 C13 1.397(6) . ?
C4 C3 1.393(6) . ?
C9 H012 0.9300 . ?
C11 C16 1.389(6) . ?
C16 H014 0.9300 . ?
C6 C1 1.380(6) . ?
C6 H015 0.9300 . ?
C12 H01A 0.9600 . ?
C12 H01B 0.9600 . ?
C12 H01C 0.9600 . ?
C3 H017 0.9300 . ?
C14 C13 1.374(7) . ?
C14 H018 0.9300 . ?
C13 H019 0.9300 . ?

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
C8 S1 C11 99.9(2) . . ?
C9 N1 C10 122.4(4) . . ?
C9 N1 C12 118.3(4) . . ?
C10 N1 C12 118.8(4) . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H005 119.1 . . ?
C4 C5 H005 119.1 . . ?
C3 C2 C1 118.5(4) . . ?
C3 C2 H006 120.8 . . ?
C1 C2 H006 120.8 . . ?
C14 C15 C16 118.8(5) . . ?
C14 C15 H007 120.6 . . ?
C16 C15 H007 120.6 . . ?
O1 C7 C8 118.8(4) . . ?
O1 C7 C4 119.7(4) . . ?
C8 C7 C4 121.6(4) . . ?
C9 C8 C7 123.0(4) . . ?
C9 C8 S1 122.0(3) . . ?
C7 C8 S1 114.4(3) . . ?
C11 C10 C13 118.1(5) . . ?
C11 C10 N1 120.9(4) . . ?
C13 C10 N1 121.1(4) . . ?
C3 C4 C5 117.3(4) . . ?
C3 C4 C7 119.1(4) . . ?
C5 C4 C7 123.4(4) . . ?
C8 C9 N1 127.2(4) . . ?
C8 C9 H012 116.4 . . ?
N1 C9 H012 116.4 . . ?
C16 C11 C10 119.2(4) . . ?
C16 C11 S1 116.6(4) . . ?
C10 C11 S1 124.1(4) . . ?
C15 C16 C11 121.9(5) . . ?
C15 C16 H014 119.1 . . ?
C11 C16 H014 119.1 . . ?
C5 C6 C1 119.7(4) . . ?
C5 C6 H015 120.2 . . ?
C1 C6 H015 120.2 . . ?
N1 C12 H01A 109.5 . . ?
N1 C12 H01B 109.5 . . ?
H01A C12 H01B 109.5 . . ?
N1 C12 H01C 109.5 . . ?
H01A C12 H01C 109.5 . . ?
H01B C12 H01C 109.5 . . ?
C2 C3 C4 122.2(4) . . ?
C2 C3 H017 118.9 . . ?
C4 C3 H017 118.9 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H018 119.9 . . ?
C15 C14 H018 119.9 . . ?
C14 C13 C10 121.6(5) . . ?
C14 C13 H019 119.2 . . ?
C10 C13 H019 119.2 . . ?
C6 C1 C2 120.5(4) . . ?
C6 C1 Br 119.4(3) . . ?
C2 C1 Br 120.1(4) . . ?

_diffrn_measured_fraction_theta_max 0.851
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.089
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
