# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1401764'
_audit_update_record             
;
2015-05-19 deposited with the CCDC.
2015-06-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration ad
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 Br N O5 S'
_chemical_formula_weight         424.26

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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                   10.47600(10)
_cell_length_b                   8.88300(10)
_cell_length_c                   18.1540(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1689.38(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    400
_cell_measurement_theta_min      12
_cell_measurement_theta_max      20

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    2.585
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8199
_exptl_absorpt_correction_T_max  0.8603
_exptl_absorpt_process_details   'Empirical absorption correction:XABS2'

_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  KappaCCD
_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            7693
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3868
_reflns_number_gt                3265
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       'HKL DENZO'
_computing_data_reduction        'HKL DENZO and SCALEPACK'
_computing_structure_solution    SHELXS-97
_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 > 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)+(0.0666P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.010(8)
_refine_ls_number_reflns         3868
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.1000
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002

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 -0.48446(4) -0.34903(4) 0.13988(2) 0.07288(16) Uani 1 1 d . . .
S S -0.26005(8) -1.03975(7) 0.00834(3) 0.04373(17) Uani 1 1 d . . .
N N -0.2763(3) -0.9210(3) -0.05829(11) 0.0449(5) Uani 1 1 d . . .
O1 O -0.3741(2) -0.9967(2) 0.06314(10) 0.0489(5) Uani 1 1 d . . .
O2 O -0.1445(2) -1.0100(3) 0.04511(11) 0.0548(6) Uani 1 1 d . . .
O3 O -0.2914(3) -1.1859(2) -0.01647(11) 0.0601(6) Uani 1 1 d . . .
O4 O -0.3226(2) -0.0658(2) -0.21771(10) 0.0513(5) Uani 1 1 d . . .
O5 O -0.4235(2) -0.4396(2) -0.39768(9) 0.0459(5) Uani 1 1 d . . .
C1 C -0.2651(3) -0.7618(3) -0.03363(13) 0.0388(6) Uani 1 1 d . . .
C2 C -0.3519(3) -0.7287(3) 0.03173(14) 0.0381(6) Uani 1 1 d . . .
C3 C -0.3819(3) -0.5811(3) 0.05090(14) 0.0416(6) Uani 1 1 d . . .
H3 H -0.3566 -0.5023 0.0205 0.050 Uiso 1 1 calc R . .
C4 C -0.4483(3) -0.5507(4) 0.11413(15) 0.0494(7) Uani 1 1 d . . .
C5 C -0.4911(3) -0.6666(4) 0.15976(18) 0.0554(8) Uani 1 1 d . . .
H5 H -0.5372 -0.6451 0.2023 0.066 Uiso 1 1 calc R . .
C6 C -0.4641(3) -0.8127(3) 0.14109(16) 0.0508(7) Uani 1 1 d . . .
H6 H -0.4926 -0.8913 0.1707 0.061 Uiso 1 1 calc R . .
C7 C -0.3947(3) -0.8429(3) 0.07824(14) 0.0396(5) Uani 1 1 d . . .
C8 C -0.2890(3) -0.6626(3) -0.09658(13) 0.0423(6) Uani 1 1 d . . .
C9 C -0.3048(3) -0.5779(3) -0.14652(14) 0.0409(6) Uani 1 1 d . . .
C10 C -0.3259(3) -0.4690(3) -0.20381(13) 0.0381(5) Uani 1 1 d . . .
C11 C -0.3125(3) -0.3183(3) -0.18700(14) 0.0415(6) Uani 1 1 d . . .
H11 H -0.2872 -0.2887 -0.1401 0.050 Uiso 1 1 calc R . .
C12 C -0.3372(3) -0.2111(3) -0.24096(13) 0.0380(6) Uani 1 1 d . . .
C13 C -0.3732(3) -0.2529(3) -0.31089(14) 0.0374(6) Uani 1 1 d . . .
H13 H -0.3896 -0.1805 -0.3467 0.045 Uiso 1 1 calc R . .
C14 C -0.3848(3) -0.4065(3) -0.32718(13) 0.0361(5) Uani 1 1 d . . .
C15 C -0.3617(3) -0.5144(3) -0.27476(14) 0.0388(6) Uani 1 1 d . . .
H15 H -0.3697 -0.6161 -0.2861 0.047 Uiso 1 1 calc R . .
C16 C -0.3204(4) 0.0506(3) -0.27120(16) 0.0507(7) Uani 1 1 d . . .
H16A H -0.3099 0.1460 -0.2471 0.061 Uiso 1 1 calc R . .
H16B H -0.3992 0.0504 -0.2982 0.061 Uiso 1 1 calc R . .
H16C H -0.2506 0.0343 -0.3045 0.061 Uiso 1 1 calc R . .
C17 C -0.4108(3) -0.5934(4) -0.42007(17) 0.0524(7) Uani 1 1 d . . .
H17A H -0.4408 -0.6044 -0.4698 0.063 Uiso 1 1 calc R . .
H17B H -0.4605 -0.6563 -0.3880 0.063 Uiso 1 1 calc R . .
H17C H -0.3227 -0.6227 -0.4174 0.063 Uiso 1 1 calc R . .
H1 H -0.179(3) -0.747(3) -0.0196(15) 0.033(7) Uiso 1 1 d . . .
H1N H -0.346(5) -0.966(7) -0.098(3) 0.123(19) 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
Br C4 1.889(3) . ?
S O2 1.407(2) . ?
S O3 1.413(2) . ?
S O1 1.601(2) . ?
S N 1.614(2) . ?
N C1 1.488(3) . ?
N H1N 1.10(6) . ?
O1 C7 1.410(3) . ?
O4 C12 1.367(3) . ?
O4 C16 1.419(3) . ?
O5 C14 1.374(3) . ?
O5 C17 1.432(4) . ?
C1 C8 1.465(3) . ?
C1 C2 1.524(4) . ?
C1 H1 0.95(3) . ?
C2 C7 1.394(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.369(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(5) . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.379(4) . ?
C6 H6 0.9300 . ?
C8 C9 1.190(4) . ?
C9 C10 1.437(3) . ?
C10 C11 1.380(4) . ?
C10 C15 1.401(4) . ?
C11 C12 1.390(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.375(4) . ?
C13 C14 1.402(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(4) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
O2 S O3 121.58(15) . . ?
O2 S O1 107.58(12) . . ?
O3 S O1 104.14(14) . . ?
O2 S N 108.87(14) . . ?
O3 S N 109.71(13) . . ?
O1 S N 103.33(12) . . ?
C1 N S 112.79(16) . . ?
C1 N H1N 127(3) . . ?
S N H1N 109(3) . . ?
C7 O1 S 117.83(17) . . ?
C12 O4 C16 118.6(2) . . ?
C14 O5 C17 116.2(2) . . ?
C8 C1 N 108.9(2) . . ?
C8 C1 C2 112.9(2) . . ?
N C1 C2 111.7(2) . . ?
C8 C1 H1 106.8(17) . . ?
N C1 H1 106.8(18) . . ?
C2 C1 H1 109.5(17) . . ?
C7 C2 C3 117.5(3) . . ?
C7 C2 C1 121.6(2) . . ?
C3 C2 C1 120.7(2) . . ?
C4 C3 C2 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.0(3) . . ?
C3 C4 Br 119.7(2) . . ?
C5 C4 Br 119.3(2) . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 119.8(3) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C2 122.0(3) . . ?
C6 C7 O1 115.5(2) . . ?
C2 C7 O1 122.5(2) . . ?
C9 C8 C1 177.3(3) . . ?
C8 C9 C10 176.7(3) . . ?
C11 C10 C15 120.7(2) . . ?
C11 C10 C9 118.5(2) . . ?
C15 C10 C9 120.8(2) . . ?
C10 C11 C12 119.3(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
O4 C12 C13 124.8(2) . . ?
O4 C12 C11 114.1(2) . . ?
C13 C12 C11 121.1(2) . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
O5 C14 C15 123.3(2) . . ?
O5 C14 C13 115.5(2) . . ?
C15 C14 C13 121.2(2) . . ?
C14 C15 C10 118.9(2) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.109
