# 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_ww
_database_code_depnum_ccdc_archive 'CCDC 1057250'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 Br N2 O2 S'
_chemical_formula_weight         401.27

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'
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   P21/c

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

_cell_length_a                   7.891(2)
_cell_length_b                   18.770(5)
_cell_length_c                   11.594(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.858(5)
_cell_angle_gamma                90.00
_cell_volume                     1704.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    2.546
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6043
_exptl_absorpt_correction_T_max  0.6299
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            8517
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.10
_reflns_number_total             3037
_reflns_number_gt                2172
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1433P)²+0.6630P] 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         3037
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0630
_refine_ls_wR_factor_ref         0.2243
_refine_ls_wR_factor_gt          0.2137
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.006
_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
Br1 Br 0.12208(5) 0.28768(2) 0.43774(3) 0.05935(12) Uani 1 1 d . . .
N1 N 0.7876(3) 0.00259(12) 0.4652(2) 0.0394(7) Uani 1 1 d . . .
O1 O 0.7177(3) 0.15345(13) 0.87146(19) 0.0550(7) Uani 1 1 d . . .
C1 C 0.8273(5) 0.11265(18) 0.3510(3) 0.0604(11) Uani 1 1 d . . .
H1A H 0.8092 0.1420 0.4130 0.072 Uiso 1 1 calc R . .
N2 N 0.7364(3) 0.04095(12) 0.54068(19) 0.0344(6) Uani 1 1 d . . .
O2 O 0.8904(2) 0.14910(11) 0.7081(2) 0.0472(6) Uani 1 1 d . . .
C2 C 0.8605(6) 0.1417(2) 0.2467(3) 0.0717(13) Uani 1 1 d . . .
H2A H 0.8680 0.1909 0.2390 0.086 Uiso 1 1 calc R . .
C3 C 0.8822(5) 0.0986(2) 0.1545(3) 0.0677(12) Uani 1 1 d . . .
H3A H 0.8980 0.1186 0.0832 0.081 Uiso 1 1 calc R . .
C4 C 0.8809(5) 0.0261(2) 0.1667(3) 0.0601(11) Uani 1 1 d . . .
H4A H 0.8984 -0.0030 0.1042 0.072 Uiso 1 1 calc R . .
C5 C 0.8536(4) -0.00390(18) 0.2711(3) 0.0451(9) Uani 1 1 d . . .
H5A H 0.8570 -0.0531 0.2800 0.054 Uiso 1 1 calc R . .
C6 C 0.8215(4) 0.03869(16) 0.3622(3) 0.0381(8) Uani 1 1 d . . .
C7 C 0.6999(4) 0.00247(14) 0.6412(2) 0.0346(8) Uani 1 1 d . . .
C8 C 0.6681(5) -0.07062(17) 0.6410(3) 0.0536(10) Uani 1 1 d . . .
H8A H 0.6747 -0.0971 0.5738 0.064 Uiso 1 1 calc R . .
C9 C 0.6270(5) -0.10365(19) 0.7395(3) 0.0592(11) Uani 1 1 d . . .
H9A H 0.6068 -0.1525 0.7386 0.071 Uiso 1 1 calc R . .
C10 C 0.6151(5) -0.06526(19) 0.8402(3) 0.0638(11) Uani 1 1 d . . .
H10A H 0.5863 -0.0880 0.9065 0.077 Uiso 1 1 calc R . .
C11 C 0.6463(4) 0.00632(19) 0.8414(3) 0.0495(9) Uani 1 1 d . . .
H11A H 0.6398 0.0323 0.9090 0.059 Uiso 1 1 calc R . .
C12 C 0.6871(3) 0.04043(15) 0.7433(2) 0.0339(8) Uani 1 1 d . . .
C13 C 0.5646(3) 0.17483(13) 0.6640(2) 0.0294(7) Uani 1 1 d . . .
C14 C 0.6002(4) 0.21774(15) 0.5725(3) 0.0377(8) Uani 1 1 d . . .
H14A H 0.7120 0.2235 0.5562 0.045 Uiso 1 1 calc R . .
C15 C 0.4677(4) 0.25183(16) 0.5058(3) 0.0443(9) Uani 1 1 d . . .
H15A H 0.4891 0.2808 0.4441 0.053 Uiso 1 1 calc R . .
C16 C 0.3031(4) 0.24239(16) 0.5321(3) 0.0359(8) Uani 1 1 d . . .
C17 C 0.2668(4) 0.20058(17) 0.6231(3) 0.0405(8) Uani 1 1 d . . .
H17A H 0.1552 0.1951 0.6398 0.049 Uiso 1 1 calc R . .
C18 C 0.4007(4) 0.16672(16) 0.6896(3) 0.0392(8) Uani 1 1 d . . .
H18A H 0.3791 0.1383 0.7519 0.047 Uiso 1 1 calc R . .
S1 S 0.73317(9) 0.13331(4) 0.75277(6) 0.03561(19) Uani 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
Br1 C16 1.894(3) . ?
N1 N2 1.237(3) . ?
N1 C6 1.426(4) . ?
O1 S1 1.446(2) . ?
C1 C2 1.379(5) . ?
C1 C6 1.396(5) . ?
N2 C7 1.429(4) . ?
O2 S1 1.431(2) . ?
C2 C3 1.368(6) . ?
C3 C4 1.369(6) . ?
C4 C5 1.375(5) . ?
C5 C6 1.372(4) . ?
C7 C8 1.395(4) . ?
C7 C12 1.396(4) . ?
C8 C9 1.372(5) . ?
C9 C10 1.385(5) . ?
C10 C11 1.366(5) . ?
C11 C12 1.376(4) . ?
C12 S1 1.782(3) . ?
C13 C18 1.370(4) . ?
C13 C14 1.387(4) . ?
C13 S1 1.764(3) . ?
C14 C15 1.381(4) . ?
C15 C16 1.381(4) . ?
C16 C17 1.372(4) . ?
C17 C18 1.385(4) . ?

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
N2 N1 C6 115.2(2) . . ?
C2 C1 C6 119.1(3) . . ?
N1 N2 C7 113.4(2) . . ?
C3 C2 C1 120.4(4) . . ?
C2 C3 C4 120.3(4) . . ?
C3 C4 C5 120.1(3) . . ?
C6 C5 C4 120.1(3) . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 N1 116.0(3) . . ?
C1 C6 N1 124.2(3) . . ?
C8 C7 C12 118.2(3) . . ?
C8 C7 N2 123.3(3) . . ?
C12 C7 N2 118.4(2) . . ?
C9 C8 C7 120.2(3) . . ?
C8 C9 C10 120.9(3) . . ?
C11 C10 C9 119.3(3) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 S1 118.1(2) . . ?
C7 C12 S1 121.1(2) . . ?
C18 C13 C14 120.9(3) . . ?
C18 C13 S1 119.4(2) . . ?
C14 C13 S1 119.7(2) . . ?
C15 C14 C13 119.2(3) . . ?
C16 C15 C14 119.1(3) . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 Br1 119.3(2) . . ?
C15 C16 Br1 118.7(2) . . ?
C16 C17 C18 118.4(3) . . ?
C13 C18 C17 120.4(3) . . ?
O2 S1 O1 117.72(14) . . ?
O2 S1 C13 108.88(13) . . ?
O1 S1 C13 107.25(13) . . ?
O2 S1 C12 111.09(13) . . ?
O1 S1 C12 105.95(14) . . ?
C13 S1 C12 105.19(12) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.145
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.132
