# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1587296'
_audit_update_record             
;
2017-11-23 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 Br N3 O5 S'
_chemical_formula_weight         478.32

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           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3579(3)
_cell_length_b                   8.8158(4)
_cell_length_c                   15.8511(7)
_cell_angle_alpha                85.4310(10)
_cell_angle_beta                 88.5430(10)
_cell_angle_gamma                72.7390(10)
_cell_volume                     978.77(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6213
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    2.244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4250
_exptl_absorpt_correction_T_max  0.5723
_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  'Bruker Apex II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11881
_diffrn_reflns_av_R_equivalents  0.0188
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         25.46
_reflns_number_total             3594
_reflns_number_gt                3163
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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 > 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)+(0.0466P)²+0.7532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3594
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0907
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
S1 S 0.64264(9) 0.15356(8) -0.46909(4) 0.03793(17) Uani 1 1 d . . .
Br1 Br 0.84170(5) -0.36041(4) 0.086326(19) 0.06539(15) Uani 1 1 d . . .
O1 O 0.7343(3) 0.0354(3) -0.52458(13) 0.0587(6) Uani 1 1 d . . .
O2 O 0.4803(3) 0.2761(3) -0.49801(15) 0.0638(6) Uani 1 1 d . . .
O3 O 0.5832(3) 0.38571(19) -0.27042(12) 0.0422(4) Uani 1 1 d . . .
O4 O 0.6581(3) 0.2987(2) -0.13600(11) 0.0415(4) Uani 1 1 d . . .
O5 O 0.9817(2) 0.20251(19) -0.31185(11) 0.0347(4) Uani 1 1 d . . .
N1 N 0.5998(3) 0.0709(2) -0.37717(12) 0.0291(4) Uani 1 1 d . . .
N2 N 0.8041(3) 0.2250(2) -0.43027(12) 0.0338(4) Uani 1 1 d . . .
N3 N 0.4302(3) 0.1311(2) -0.25668(13) 0.0340(4) Uani 1 1 d . . .
C1 C 0.6821(3) -0.0080(3) -0.15376(14) 0.0289(5) Uani 1 1 d . . .
C2 C 0.5518(4) -0.0790(3) -0.11713(16) 0.0356(5) Uani 1 1 d . . .
H2A H 0.4314 -0.0564 -0.1407 0.043 Uiso 1 1 calc R . .
C3 C 0.5997(4) -0.1836(3) -0.04542(17) 0.0417(6) Uani 1 1 d . . .
H3A H 0.5115 -0.2302 -0.0206 0.050 Uiso 1 1 calc R . .
C4 C 0.7773(4) -0.2175(3) -0.01179(16) 0.0412(6) Uani 1 1 d . . .
C5 C 0.9100(4) -0.1478(3) -0.04678(17) 0.0436(6) Uani 1 1 d . . .
H5A H 1.0306 -0.1719 -0.0232 0.052 Uiso 1 1 calc R . .
C6 C 0.8605(4) -0.0417(3) -0.11735(16) 0.0376(5) Uani 1 1 d . . .
H6A H 0.9477 0.0075 -0.1407 0.045 Uiso 1 1 calc R . .
C7 C 0.8816(3) -0.1188(3) -0.30717(14) 0.0286(5) Uani 1 1 d . . .
C8 C 0.7998(4) -0.2402(3) -0.31286(17) 0.0397(6) Uani 1 1 d . . .
H8A H 0.6700 -0.2160 -0.3229 0.048 Uiso 1 1 calc R . .
C9 C 0.9114(5) -0.3977(3) -0.30354(19) 0.0505(7) Uani 1 1 d . . .
H9A H 0.8556 -0.4790 -0.3068 0.061 Uiso 1 1 calc R . .
C10 C 1.1032(5) -0.4348(3) -0.28955(18) 0.0530(8) Uani 1 1 d . . .
H10A H 1.1773 -0.5407 -0.2831 0.064 Uiso 1 1 calc R . .
C11 C 1.1856(4) -0.3148(3) -0.28507(19) 0.0515(7) Uani 1 1 d . . .
H11A H 1.3161 -0.3398 -0.2766 0.062 Uiso 1 1 calc R . .
C12 C 1.0757(4) -0.1567(3) -0.29314(17) 0.0390(6) Uani 1 1 d . . .
H12A H 1.1321 -0.0761 -0.2891 0.047 Uiso 1 1 calc R . .
C13 C 0.6276(3) 0.1084(3) -0.23119(14) 0.0275(5) Uani 1 1 d . . .
C14 C 0.7530(3) 0.0532(3) -0.31459(13) 0.0243(4) Uani 1 1 d . . .
C15 C 0.4242(3) 0.1221(3) -0.33518(16) 0.0338(5) Uani 1 1 d . . .
H15A H 0.3093 0.1480 -0.3641 0.041 Uiso 1 1 calc R . .
C16 C 0.6234(3) 0.2807(3) -0.21523(15) 0.0296(5) Uani 1 1 d . . .
C17 C 0.6355(5) 0.4617(3) -0.1169(2) 0.0530(7) Uani 1 1 d . . .
H17A H 0.6633 0.4637 -0.0582 0.080 Uiso 1 1 calc R . .
H17B H 0.5069 0.5255 -0.1284 0.080 Uiso 1 1 calc R . .
H17C H 0.7213 0.5036 -0.1513 0.080 Uiso 1 1 calc R . .
C18 C 0.8611(3) 0.1689(2) -0.34934(14) 0.0268(5) Uani 1 1 d . . .
C19 C 0.8908(5) 0.3289(3) -0.48349(18) 0.0499(7) Uani 1 1 d . . .
H19A H 0.9809 0.3587 -0.4507 0.075 Uiso 1 1 calc R . .
H19B H 0.7935 0.4228 -0.5041 0.075 Uiso 1 1 calc R . .
H19C H 0.9547 0.2731 -0.5305 0.075 Uiso 1 1 calc R . .


_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
S1 O2 1.410(2) . ?
S1 O1 1.419(2) . ?
S1 N1 1.6422(19) . ?
S1 N2 1.652(2) . ?
Br1 C4 1.898(2) . ?
O3 C16 1.197(3) . ?
O4 C16 1.319(3) . ?
O4 C17 1.452(3) . ?
O5 C18 1.200(3) . ?
N1 C15 1.405(3) . ?
N1 C14 1.485(3) . ?
N2 C18 1.367(3) . ?
N2 C19 1.467(3) . ?
N3 C15 1.256(3) . ?
N3 C13 1.469(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.387(3) . ?
C1 C13 1.517(3) . ?
C2 C3 1.389(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(4) . ?
C5 C6 1.382(4) . ?
C5 H5A 0.9300 . ?
C6 H6A 0.9300 . ?
C7 C8 1.384(3) . ?
C7 C12 1.386(3) . ?
C7 C14 1.527(3) . ?
C8 C9 1.387(4) . ?
C8 H8A 0.9300 . ?
C9 C10 1.371(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.374(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.385(4) . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C16 1.550(3) . ?
C13 C14 1.616(3) . ?
C14 C18 1.532(3) . ?
C15 H15A 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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 S1 O1 118.73(15) . . ?
O2 S1 N1 110.48(13) . . ?
O1 S1 N1 110.65(12) . . ?
O2 S1 N2 111.80(13) . . ?
O1 S1 N2 108.63(12) . . ?
N1 S1 N2 93.71(9) . . ?
C16 O4 C17 115.1(2) . . ?
C15 N1 C14 107.93(18) . . ?
C15 N1 S1 122.69(16) . . ?
C14 N1 S1 112.50(14) . . ?
C18 N2 C19 123.5(2) . . ?
C18 N2 S1 115.30(15) . . ?
C19 N2 S1 120.88(18) . . ?
C15 N3 C13 109.39(19) . . ?
C2 C1 C6 119.1(2) . . ?
C2 C1 C13 120.2(2) . . ?
C6 C1 C13 120.7(2) . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2A 119.8 . . ?
C3 C2 H2A 119.8 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 121.4(2) . . ?
C3 C4 Br1 119.2(2) . . ?
C5 C4 Br1 119.4(2) . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C5 C6 C1 120.7(2) . . ?
C5 C6 H6A 119.7 . . ?
C1 C6 H6A 119.7 . . ?
C8 C7 C12 119.3(2) . . ?
C8 C7 C14 118.5(2) . . ?
C12 C7 C14 122.2(2) . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8A 120.0 . . ?
C9 C8 H8A 120.0 . . ?
C10 C9 C8 120.5(3) . . ?
C10 C9 H9A 119.7 . . ?
C8 C9 H9A 119.7 . . ?
C9 C10 C11 119.7(2) . . ?
C9 C10 H10A 120.2 . . ?
C11 C10 H10A 120.2 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 H12A 120.0 . . ?
C7 C12 H12A 120.0 . . ?
N3 C13 C1 111.42(18) . . ?
N3 C13 C16 101.77(17) . . ?
C1 C13 C16 113.58(18) . . ?
N3 C13 C14 104.76(17) . . ?
C1 C13 C14 114.48(18) . . ?
C16 C13 C14 109.73(17) . . ?
N1 C14 C7 110.00(17) . . ?
N1 C14 C18 104.93(17) . . ?
C7 C14 C18 111.69(17) . . ?
N1 C14 C13 100.49(16) . . ?
C7 C14 C13 114.69(17) . . ?
C18 C14 C13 113.92(17) . . ?
N3 C15 N1 116.6(2) . . ?
N3 C15 H15A 121.7 . . ?
N1 C15 H15A 121.7 . . ?
O3 C16 O4 124.9(2) . . ?
O3 C16 C13 121.3(2) . . ?
O4 C16 C13 113.68(19) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 N2 124.8(2) . . ?
O5 C18 C14 125.0(2) . . ?
N2 C18 C14 110.15(18) . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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
O2 S1 N1 C15 -1.1(2) . . . . ?
O1 S1 N1 C15 -134.67(19) . . . . ?
N2 S1 N1 C15 113.82(18) . . . . ?
O2 S1 N1 C14 -132.53(17) . . . . ?
O1 S1 N1 C14 93.90(17) . . . . ?
N2 S1 N1 C14 -17.61(17) . . . . ?
O2 S1 N2 C18 124.81(19) . . . . ?
O1 S1 N2 C18 -102.25(19) . . . . ?
N1 S1 N2 C18 11.00(19) . . . . ?
O2 S1 N2 C19 -60.9(2) . . . . ?
O1 S1 N2 C19 72.0(2) . . . . ?
N1 S1 N2 C19 -174.8(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C13 C1 C2 C3 -178.9(2) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C4 Br1 179.90(19) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
Br1 C4 C5 C6 -178.9(2) . . . . ?
C4 C5 C6 C1 -1.4(4) . . . . ?
C2 C1 C6 C5 1.7(4) . . . . ?
C13 C1 C6 C5 180.0(2) . . . . ?
C12 C7 C8 C9 0.8(4) . . . . ?
C14 C7 C8 C9 -177.8(2) . . . . ?
C7 C8 C9 C10 -0.7(4) . . . . ?
C8 C9 C10 C11 -0.3(4) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C11 C12 C7 -1.0(4) . . . . ?
C8 C7 C12 C11 0.1(4) . . . . ?
C14 C7 C12 C11 178.6(2) . . . . ?
C15 N3 C13 C1 -133.4(2) . . . . ?
C15 N3 C13 C16 105.2(2) . . . . ?
C15 N3 C13 C14 -9.1(2) . . . . ?
C2 C1 C13 N3 0.7(3) . . . . ?
C6 C1 C13 N3 -177.6(2) . . . . ?
C2 C1 C13 C16 114.9(2) . . . . ?
C6 C1 C13 C16 -63.4(3) . . . . ?
C2 C1 C13 C14 -117.9(2) . . . . ?
C6 C1 C13 C14 63.8(3) . . . . ?
C15 N1 C14 C7 119.95(19) . . . . ?
S1 N1 C14 C7 -101.59(17) . . . . ?
C15 N1 C14 C18 -119.78(19) . . . . ?
S1 N1 C14 C18 18.7(2) . . . . ?
C15 N1 C14 C13 -1.3(2) . . . . ?
S1 N1 C14 C13 137.11(14) . . . . ?
C8 C7 C14 N1 -36.4(3) . . . . ?
C12 C7 C14 N1 145.1(2) . . . . ?
C8 C7 C14 C18 -152.5(2) . . . . ?
C12 C7 C14 C18 29.0(3) . . . . ?
C8 C7 C14 C13 76.0(3) . . . . ?
C12 C7 C14 C13 -102.6(2) . . . . ?
N3 C13 C14 N1 5.9(2) . . . . ?
C1 C13 C14 N1 128.20(18) . . . . ?
C16 C13 C14 N1 -102.72(18) . . . . ?
N3 C13 C14 C7 -112.0(2) . . . . ?
C1 C13 C14 C7 10.3(3) . . . . ?
C16 C13 C14 C7 139.38(19) . . . . ?
N3 C13 C14 C18 117.51(19) . . . . ?
C1 C13 C14 C18 -120.2(2) . . . . ?
C16 C13 C14 C18 8.9(2) . . . . ?
C13 N3 C15 N1 9.1(3) . . . . ?
C14 N1 C15 N3 -4.8(3) . . . . ?
S1 N1 C15 N3 -138.0(2) . . . . ?
C17 O4 C16 O3 2.9(4) . . . . ?
C17 O4 C16 C13 -173.8(2) . . . . ?
N3 C13 C16 O3 -60.3(3) . . . . ?
C1 C13 C16 O3 179.9(2) . . . . ?
C14 C13 C16 O3 50.3(3) . . . . ?
N3 C13 C16 O4 116.5(2) . . . . ?
C1 C13 C16 O4 -3.4(3) . . . . ?
C14 C13 C16 O4 -132.93(19) . . . . ?
C19 N2 C18 O5 3.1(4) . . . . ?
S1 N2 C18 O5 177.14(19) . . . . ?
C19 N2 C18 C14 -175.3(2) . . . . ?
S1 N2 C18 C14 -1.2(2) . . . . ?
N1 C14 C18 O5 171.0(2) . . . . ?
C7 C14 C18 O5 -69.8(3) . . . . ?
C13 C14 C18 O5 62.1(3) . . . . ?
N1 C14 C18 N2 -10.7(2) . . . . ?
C7 C14 C18 N2 108.5(2) . . . . ?
C13 C14 C18 N2 -119.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.46
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.768
_refine_diff_density_rms         0.058
