# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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. 
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data_mo_dm16821_0m
_database_code_depnum_ccdc_archive 'CCDC 1534259'
_audit_update_record             
;
2017-02-22 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;
_audit_creation_date             2016-12-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 Br N O4 S'
_chemical_formula_sum            'C11 H10 Br N O4 S'
_chemical_formula_weight         332.17
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   8.1512(10)
_cell_length_b                   16.7902(19)
_cell_length_c                   9.2892(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.105(2)
_cell_angle_gamma                90
_cell_volume                     1261.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3381
_cell_measurement_temperature    296
_cell_measurement_theta_max      25.92
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.627
_shelx_estimated_absorpt_T_min   0.519
_exptl_absorpt_coefficient_mu    3.429
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1077 before and 0.0334 after correction.
The Ratio of minimum to maximum transmission is 0.6786.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12685
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.616
_diffrn_reflns_theta_min         2.426
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2707
_reflns_number_total             3898
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.443
_refine_diff_density_min         -1.175
_refine_diff_density_rms         0.123
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         3898
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.2092P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1101
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.80939(4) 0.23790(2) 0.68318(3) 0.05456(12) Uani 1 1 d . . . . .
S1 S 0.20448(7) 0.33977(4) 0.60269(7) 0.04060(16) Uani 1 1 d . . . . .
O1 O 0.2764(2) 0.46554(12) 0.3817(2) 0.0554(5) Uani 1 1 d . . . . .
O2 O 0.5355(2) 0.42154(11) 0.3827(2) 0.0481(4) Uani 1 1 d . . . . .
O3 O 0.0704(2) 0.35105(13) 0.4912(2) 0.0561(5) Uani 1 1 d . . . . .
O4 O 0.2333(3) 0.26413(11) 0.6694(2) 0.0523(5) Uani 1 1 d . . . . .
N1 N 0.3789(2) 0.35898(12) 0.5270(2) 0.0363(4) Uani 1 1 d . . . . .
C1 C 0.3858(3) 0.42035(14) 0.4254(3) 0.0395(5) Uani 1 1 d . . . . .
C2 C 0.6424(3) 0.36285(15) 0.4606(3) 0.0446(6) Uani 1 1 d . . . . .
H2A H 0.738101 0.388100 0.514248 0.053 Uiso 1 1 calc R . . . .
H2B H 0.679754 0.324169 0.394212 0.053 Uiso 1 1 calc R . . . .
C3 C 0.5369(3) 0.32386(13) 0.5618(2) 0.0348(5) Uani 1 1 d . . . . .
C4 C 0.5862(3) 0.26995(15) 0.6621(3) 0.0437(6) Uani 1 1 d . . . . .
H4 H 0.512520 0.248505 0.720499 0.052 Uiso 1 1 calc R . . . .
C5 C 0.2031(3) 0.41303(15) 0.7354(3) 0.0393(5) Uani 1 1 d . . . . .
C6 C 0.1118(3) 0.48218(17) 0.7063(3) 0.0504(7) Uani 1 1 d . . . . .
H6 H 0.049736 0.489440 0.616364 0.060 Uiso 1 1 calc R . . . .
C7 C 0.1139(4) 0.53965(18) 0.8111(3) 0.0567(7) Uani 1 1 d . . . . .
H7 H 0.052936 0.586007 0.790927 0.068 Uiso 1 1 calc R . . . .
C8 C 0.2043(4) 0.53048(17) 0.9460(3) 0.0508(6) Uani 1 1 d . . . . .
C9 C 0.2939(5) 0.4602(2) 0.9741(3) 0.0633(8) Uani 1 1 d . . . . .
H9 H 0.354611 0.452773 1.064606 0.076 Uiso 1 1 calc R . . . .
C10 C 0.2942(4) 0.40164(18) 0.8700(3) 0.0548(7) Uani 1 1 d . . . . .
H10 H 0.354698 0.355114 0.889939 0.066 Uiso 1 1 calc R . . . .
C11 C 0.2069(5) 0.5944(2) 1.0601(4) 0.0721(10) Uani 1 1 d . . . . .
H11A H 0.285366 0.634808 1.042267 0.108 Uiso 1 1 calc GR . . . .
H11B H 0.238124 0.571509 1.154179 0.108 Uiso 1 1 calc GR . . . .
H11C H 0.098978 0.617771 1.056562 0.108 Uiso 1 1 calc GR . . . .


_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 C4 1.884(3) . ?
S1 O3 1.422(2) . ?
S1 O4 1.420(2) . ?
S1 N1 1.693(2) . ?
S1 C5 1.742(3) . ?
O1 C1 1.203(3) . ?
O2 C1 1.328(3) . ?
O2 C2 1.448(3) . ?
N1 C1 1.403(3) . ?
N1 C3 1.417(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.501(3) . ?
C3 C4 1.325(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 C10 1.386(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.369(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.382(4) . ?
C8 C9 1.395(4) . ?
C8 C11 1.507(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(4) . ?
C10 H10 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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
O3 S1 N1 106.34(11) . . ?
O3 S1 C5 110.47(12) . . ?
O4 S1 O3 120.52(13) . . ?
O4 S1 N1 104.45(11) . . ?
O4 S1 C5 109.73(12) . . ?
N1 S1 C5 103.79(11) . . ?
C1 O2 C2 111.04(19) . . ?
C1 N1 S1 121.66(17) . . ?
C1 N1 C3 110.35(19) . . ?
C3 N1 S1 127.76(16) . . ?
O1 C1 O2 124.1(2) . . ?
O1 C1 N1 126.9(2) . . ?
O2 C1 N1 109.1(2) . . ?
O2 C2 H2A 110.8 . . ?
O2 C2 H2B 110.8 . . ?
O2 C2 C3 104.7(2) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
N1 C3 C2 104.52(19) . . ?
C4 C3 N1 129.2(2) . . ?
C4 C3 C2 126.2(2) . . ?
Br1 C4 H4 120.9 . . ?
C3 C4 Br1 118.2(2) . . ?
C3 C4 H4 120.9 . . ?
C6 C5 S1 120.2(2) . . ?
C10 C5 S1 119.4(2) . . ?
C10 C5 C6 120.4(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.3 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.6(3) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 C9 118.2(3) . . ?
C7 C8 C11 121.2(3) . . ?
C9 C8 C11 120.6(3) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C5 C10 H10 120.4 . . ?
C9 C10 C5 119.1(3) . . ?
C9 C10 H10 120.4 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
