# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_AA
_database_code_depnum_ccdc_archive 'CCDC 1966259'
loop_
_audit_author_name
_audit_author_address
'Biraj Jyoti Borah'
;Tezpur University
India
;
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2019-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br N O4 S'
_chemical_formula_weight         424.29

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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   18.5372(6)
_cell_length_b                   18.5372(6)
_cell_length_c                   10.4950(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3606.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      19.07


_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             2482
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    2.418
_shelx_estimated_absorpt_T_min   0.119
_shelx_estimated_absorpt_T_max   0.181
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.038
_exptl_absorpt_correction_T_max  0.074
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52966
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.554
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3188
_reflns_number_gt                2672
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.976

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+2.4662P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1123 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0610
_refine_ls_wR_factor_gt          0.0558
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38541(3) 0.52320(3) 0.89812(5) 0.0721(2) Uani 1 1 d . . . . .
S1 S 0.28121(6) 0.28960(6) 0.48911(11) 0.0415(3) Uani 1 1 d . . . . .
O1 O 0.33820(16) 0.27977(16) 0.3992(4) 0.0542(8) Uani 1 1 d . . . . .
O2 O 0.25307(19) 0.22757(15) 0.5532(3) 0.0549(9) Uani 1 1 d . . . . .
O3 O 0.11015(16) 0.41671(15) 0.2891(3) 0.0429(8) Uani 1 1 d . . . . .
N1 N 0.21493(17) 0.32991(17) 0.4137(3) 0.0340(8) Uani 1 1 d . . . . .
C1 C 0.3079(2) 0.3535(2) 0.6037(4) 0.0370(9) Uani 1 1 d . . . . .
C2 C 0.3314(2) 0.4207(2) 0.5623(4) 0.0395(11) Uani 1 1 d . . . . .
O4 O 0.33573(16) 0.43714(16) 0.4337(2) 0.0413(8) Uani 1 1 d . . . . .
C3 C 0.2689(2) 0.4539(2) 0.3624(4) 0.0388(11) Uani 1 1 d . . . . .
C4 C 0.2368(2) 0.3822(2) 0.3128(4) 0.0352(10) Uani 1 1 d . . . . .
H4 H 0.2749 0.3587 0.2630 0.042 Uiso 1 1 calc R U . . .
C5 C 0.1720(2) 0.3891(3) 0.2256(4) 0.0429(11) Uani 1 1 d . . . . .
H5A H 0.1842 0.4209 0.1553 0.051 Uiso 1 1 calc R U . . .
H5B H 0.1606 0.3421 0.1904 0.051 Uiso 1 1 calc R U . . .
C6 C 0.0948(2) 0.3834(2) 0.4034(4) 0.0354(9) Uani 1 1 d . . . . .
C7 C 0.0270(2) 0.3980(2) 0.4548(4) 0.0439(12) Uani 1 1 d . . . . .
H7 H -0.0043 0.4284 0.4111 0.053 Uiso 1 1 calc R U . . .
C8 C 0.0054(3) 0.3684(3) 0.5690(5) 0.0505(13) Uani 1 1 d . . . . .
C9 C 0.0529(3) 0.3228(3) 0.6299(4) 0.0524(13) Uani 1 1 d . . . . .
H9 H 0.0386 0.3005 0.7052 0.063 Uiso 1 1 calc R U . . .
C10 C 0.1211(2) 0.3092(2) 0.5824(4) 0.0465(12) Uani 1 1 d . . . . .
H10 H 0.1522 0.2793 0.6276 0.056 Uiso 1 1 calc R U . . .
C11 C 0.1441(2) 0.3397(2) 0.4677(4) 0.0343(10) Uani 1 1 d . . . . .
C12 C 0.3551(2) 0.4715(3) 0.6496(4) 0.0456(12) Uani 1 1 d . . . . .
H12 H 0.3724 0.5160 0.6227 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3522(3) 0.4544(2) 0.7780(4) 0.0437(11) Uani 1 1 d . . . . .
C14 C 0.3258(2) 0.3892(3) 0.8207(4) 0.0493(12) Uani 1 1 d . . . . .
H14 H 0.3229 0.3798 0.9075 0.059 Uiso 1 1 calc R U . . .
C15 C 0.3039(2) 0.3383(3) 0.7334(4) 0.0437(11) Uani 1 1 d . . . . .
H15 H 0.2866 0.2939 0.7610 0.052 Uiso 1 1 calc R U . . .
C16 C 0.2977(3) 0.4977(3) 0.2498(5) 0.0634(15) Uani 1 1 d . . . . .
H16A H 0.3266 0.4673 0.1964 0.095 Uiso 1 1 calc R U . . .
H16B H 0.3265 0.5370 0.2809 0.095 Uiso 1 1 calc R U . . .
H16C H 0.2579 0.5164 0.2014 0.095 Uiso 1 1 calc R U . . .
C17 C 0.2192(3) 0.4996(2) 0.4441(4) 0.0481(12) Uani 1 1 d . . . . .
H17A H 0.2454 0.5399 0.4776 0.072 Uiso 1 1 calc R U . . .
H17B H 0.2009 0.4710 0.5131 0.072 Uiso 1 1 calc R U . . .
H17C H 0.1797 0.5167 0.3931 0.072 Uiso 1 1 calc R U . . .
C19 C -0.0681(3) 0.3859(4) 0.6244(6) 0.0811(18) Uani 1 1 d . . . . .
H19A H -0.0672 0.3789 0.7150 0.122 Uiso 1 1 calc R U . . .
H19B H -0.1037 0.3548 0.5872 0.122 Uiso 1 1 calc R U . . .
H19C H -0.0800 0.4353 0.6060 0.122 Uiso 1 1 calc R U . . .


_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 C13 1.896(4) . ?
S1 O1 1.428(4) . ?
S1 O2 1.431(3) . ?
S1 N1 1.641(3) . ?
S1 C1 1.758(4) . ?
O3 C6 1.379(5) . ?
O3 C5 1.421(5) . ?
N1 C11 1.442(5) . ?
N1 C4 1.492(5) . ?
C1 C2 1.389(6) . ?
C1 C15 1.392(6) . ?
C2 C12 1.385(6) . ?
C2 O4 1.386(5) . ?
O4 C3 1.480(5) . ?
C3 C17 1.517(6) . ?
C3 C16 1.530(6) . ?
C3 C4 1.546(6) . ?
C4 C5 1.516(6) . ?
C6 C7 1.393(6) . ?
C6 C11 1.395(6) . ?
C7 C8 1.378(6) . ?
C8 C9 1.376(7) . ?
C8 C19 1.517(7) . ?
C9 C10 1.383(7) . ?
C10 C11 1.396(6) . ?
C12 C13 1.385(6) . ?
C13 C14 1.378(6) . ?
C14 C15 1.377(6) . ?

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
O1 S1 O2 118.54(19) . . ?
O1 S1 N1 107.04(19) . . ?
O2 S1 N1 108.63(18) . . ?
O1 S1 C1 109.3(2) . . ?
O2 S1 C1 108.8(2) . . ?
N1 S1 C1 103.49(18) . . ?
C6 O3 C5 114.4(3) . . ?
C11 N1 C4 116.4(3) . . ?
C11 N1 S1 123.3(3) . . ?
C4 N1 S1 115.7(3) . . ?
C2 C1 C15 120.2(4) . . ?
C2 C1 S1 118.6(4) . . ?
C15 C1 S1 121.2(3) . . ?
C12 C2 O4 118.4(4) . . ?
C12 C2 C1 120.2(4) . . ?
O4 C2 C1 121.3(4) . . ?
C2 O4 C3 119.4(3) . . ?
O4 C3 C17 109.9(3) . . ?
O4 C3 C16 102.2(3) . . ?
C17 C3 C16 110.6(4) . . ?
O4 C3 C4 108.1(3) . . ?
C17 C3 C4 115.8(4) . . ?
C16 C3 C4 109.3(4) . . ?
N1 C4 C5 105.5(3) . . ?
N1 C4 C3 115.1(3) . . ?
C5 C4 C3 115.8(3) . . ?
O3 C5 C4 112.8(3) . . ?
O3 C6 C7 115.8(4) . . ?
O3 C6 C11 123.1(4) . . ?
C7 C6 C11 121.1(4) . . ?
C8 C7 C6 121.5(4) . . ?
C9 C8 C7 117.5(4) . . ?
C9 C8 C19 121.9(5) . . ?
C7 C8 C19 120.6(5) . . ?
C8 C9 C10 121.9(4) . . ?
C9 C10 C11 121.1(4) . . ?
C6 C11 C10 116.9(4) . . ?
C6 C11 N1 118.7(4) . . ?
C10 C11 N1 124.5(4) . . ?
C13 C12 C2 118.4(4) . . ?
C14 C13 C12 122.0(4) . . ?
C14 C13 Br1 119.3(4) . . ?
C12 C13 Br1 118.7(4) . . ?
C15 C14 C13 119.3(4) . . ?
C14 C15 C1 119.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C11 170.7(3) . . . . ?
O2 S1 N1 C11 41.6(4) . . . . ?
C1 S1 N1 C11 -73.9(3) . . . . ?
O1 S1 N1 C4 -33.9(3) . . . . ?
O2 S1 N1 C4 -163.0(3) . . . . ?
C1 S1 N1 C4 81.5(3) . . . . ?
O1 S1 C1 C2 54.4(4) . . . . ?
O2 S1 C1 C2 -174.8(3) . . . . ?
N1 S1 C1 C2 -59.4(4) . . . . ?
O1 S1 C1 C15 -127.2(4) . . . . ?
O2 S1 C1 C15 3.6(4) . . . . ?
N1 S1 C1 C15 119.0(4) . . . . ?
C15 C1 C2 C12 3.7(7) . . . . ?
S1 C1 C2 C12 -177.9(3) . . . . ?
C15 C1 C2 O4 -179.9(4) . . . . ?
S1 C1 C2 O4 -1.5(6) . . . . ?
C12 C2 O4 C3 -106.9(5) . . . . ?
C1 C2 O4 C3 76.7(5) . . . . ?
C2 O4 C3 C17 39.8(5) . . . . ?
C2 O4 C3 C16 157.3(4) . . . . ?
C2 O4 C3 C4 -87.5(4) . . . . ?
C11 N1 C4 C5 -44.6(4) . . . . ?
S1 N1 C4 C5 158.4(3) . . . . ?
C11 N1 C4 C3 84.4(4) . . . . ?
S1 N1 C4 C3 -72.7(4) . . . . ?
O4 C3 C4 N1 62.3(4) . . . . ?
C17 C3 C4 N1 -61.5(5) . . . . ?
C16 C3 C4 N1 172.8(4) . . . . ?
O4 C3 C4 C5 -174.0(3) . . . . ?
C17 C3 C4 C5 62.2(5) . . . . ?
C16 C3 C4 C5 -63.5(5) . . . . ?
C6 O3 C5 C4 -48.2(5) . . . . ?
N1 C4 C5 O3 61.6(4) . . . . ?
C3 C4 C5 O3 -66.9(5) . . . . ?
C5 O3 C6 C7 -166.9(4) . . . . ?
C5 O3 C6 C11 15.3(5) . . . . ?
O3 C6 C7 C8 -179.6(4) . . . . ?
C11 C6 C7 C8 -1.7(6) . . . . ?
C6 C7 C8 C9 -1.0(6) . . . . ?
C6 C7 C8 C19 179.0(5) . . . . ?
C7 C8 C9 C10 2.8(7) . . . . ?
C19 C8 C9 C10 -177.1(5) . . . . ?
C8 C9 C10 C11 -2.0(7) . . . . ?
O3 C6 C11 C10 -179.8(4) . . . . ?
C7 C6 C11 C10 2.5(6) . . . . ?
O3 C6 C11 N1 1.3(6) . . . . ?
C7 C6 C11 N1 -176.3(3) . . . . ?
C9 C10 C11 C6 -0.7(6) . . . . ?
C9 C10 C11 N1 178.1(4) . . . . ?
C4 N1 C11 C6 15.9(5) . . . . ?
S1 N1 C11 C6 171.0(3) . . . . ?
C4 N1 C11 C10 -162.9(4) . . . . ?
S1 N1 C11 C10 -7.7(5) . . . . ?
O4 C2 C12 C13 -178.6(4) . . . . ?
C1 C2 C12 C13 -2.1(7) . . . . ?
C2 C12 C13 C14 -1.0(7) . . . . ?
C2 C12 C13 Br1 179.3(3) . . . . ?
C12 C13 C14 C15 2.4(7) . . . . ?
Br1 C13 C14 C15 -177.9(3) . . . . ?
C13 C14 C15 C1 -0.8(7) . . . . ?
C2 C1 C15 C14 -2.2(7) . . . . ?
S1 C1 C15 C14 179.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C17 H17C O3 0.96 2.51 3.014(6) 113.0 .
C10 H10 O2 0.93 2.24 2.893(6) 126.5 .
C7 H7 O3 0.93 2.66 3.280(5) 124.9 7_455
C5 H5B O2 0.97 2.51 3.144(5) 122.8 6_554
C17 H17C O3 0.96 2.51 3.014(6) 113.0 .
C10 H10 O2 0.93 2.24 2.893(6) 126.5 .
C7 H7 O3 0.93 2.66 3.280(5) 124.9 7_455
C5 H5B O2 0.97 2.51 3.144(5) 122.8 6_554
C17 H17C O3 0.96 2.51 3.014(6) 113.0 .
C10 H10 O2 0.93 2.24 2.893(6) 126.5 .
C7 H7 O3 0.93 2.66 3.280(5) 124.9 7_455
C5 H5B O2 0.97 2.51 3.144(5) 122.8 6_554
C10 H10 O2 0.93 2.24 2.893(6) 126.5 .
C5 H5B O2 0.97 2.51 3.144(5) 122.8 6_554
C7 H7 O3 0.93 2.66 3.280(5) 124.9 7_455
C10 H10 O2 0.93 2.24 2.893(6) 126.5 .
C17 H17C O3 0.96 2.51 3.014(6) 113.0 .
C5 H5B O2 0.97 2.51 3.144(5) 122.8 6_554
C7 H7 O3 0.93 2.66 3.280(5) 124.9 7_455
C10 H10 O2 0.93 2.24 2.893(6) 126.5 .
C17 H17C O3 0.96 2.51 3.014(6) 113.0 .

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.041

_shelxl_version_number           2014-3

