# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc1lnbn7
_database_code_depnum_ccdc_archive 'CCDC 1479309'
_audit_update_record             
;
2016-05-11 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 Br N O4 S'
_chemical_formula_weight         390.29

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.1680(5)
_cell_length_b                   10.0269(12)
_cell_length_c                   32.073(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1662.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6499
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6228
_exptl_absorpt_correction_T_max  0.7443
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            16927
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         3.25
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3804
_reflns_number_gt                3599
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_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)+(0.0127P)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   0.007(5)
_refine_ls_number_reflns         3804
_refine_ls_number_parameters     207
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0198
_refine_ls_R_factor_gt           0.0186
_refine_ls_wR_factor_ref         0.0444
_refine_ls_wR_factor_gt          0.0443
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.002
_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 0.67147(3) 0.519963(18) 0.043752(5) 0.01406(5) Uani 1 1 d . . .
S1 S 0.14534(9) 0.32254(4) 0.100435(13) 0.01165(9) Uani 1 1 d . . .
O3 O 0.7173(3) 0.06983(15) 0.10275(4) 0.0215(3) Uani 1 1 d . . .
C7 C 0.3547(4) 0.44598(17) 0.12566(5) 0.0101(3) Uani 1 1 d . . .
H7 H 0.5391 0.4242 0.1191 0.012 Uiso 1 1 calc R . .
O2 O 0.4393(2) 0.41350(15) 0.23617(4) 0.0135(3) Uani 1 1 d . . .
N1 N 0.3187(3) 0.44075(15) 0.17061(4) 0.0110(3) Uani 1 1 d D . .
O1 O 0.7477(2) 0.44709(15) 0.18616(4) 0.0159(3) Uani 1 1 d . . .
O4 O 0.4924(3) 0.15072(15) 0.04859(4) 0.0202(3) Uani 1 1 d . . .
C2 C 0.3460(4) 0.74475(18) 0.05140(5) 0.0163(4) Uani 1 1 d . . .
H2 H 0.4331 0.7734 0.0269 0.020 Uiso 1 1 calc R . .
C11 C 0.5226(3) 0.43450(19) 0.19683(5) 0.0105(4) Uani 1 1 d . . .
C6 C 0.2884(3) 0.57928(18) 0.10628(5) 0.0099(3) Uani 1 1 d . . .
C1 C 0.4096(3) 0.62468(19) 0.06990(5) 0.0115(4) Uani 1 1 d . . .
C9 C 0.5299(4) 0.12610(19) 0.08910(6) 0.0129(4) Uani 1 1 d . . .
C5 C 0.0918(3) 0.65911(19) 0.12286(6) 0.0130(4) Uani 1 1 d . . .
H5 H 0.0023 0.6300 0.1471 0.016 Uiso 1 1 calc R . .
C15 C 0.7891(4) 0.2690(2) 0.26140(6) 0.0182(4) Uani 1 1 d . . .
H15A H 0.6745 0.1939 0.2550 0.027 Uiso 1 1 calc R . .
H15B H 0.8947 0.2475 0.2859 0.027 Uiso 1 1 calc R . .
H15C H 0.9024 0.2863 0.2375 0.027 Uiso 1 1 calc R . .
C12 C 0.6284(4) 0.3918(2) 0.27035(5) 0.0143(4) Uani 1 1 d . . .
C3 C 0.1528(4) 0.82336(19) 0.06909(6) 0.0182(4) Uani 1 1 d . . .
H3 H 0.1087 0.9065 0.0568 0.022 Uiso 1 1 calc R . .
C8 C 0.3052(4) 0.17037(19) 0.11586(5) 0.0142(4) Uani 1 1 d . . .
H8A H 0.3684 0.1816 0.1448 0.017 Uiso 1 1 calc R . .
H8B H 0.1751 0.0979 0.1162 0.017 Uiso 1 1 calc R . .
C14 C 0.4527(4) 0.3689(3) 0.30774(6) 0.0319(6) Uani 1 1 d . . .
H14A H 0.3404 0.4467 0.3116 0.048 Uiso 1 1 calc R . .
H14B H 0.5584 0.3558 0.3328 0.048 Uiso 1 1 calc R . .
H14C H 0.3462 0.2895 0.3029 0.048 Uiso 1 1 calc R . .
C4 C 0.0246(4) 0.7799(2) 0.10475(6) 0.0160(4) Uani 1 1 d . . .
H4 H -0.1087 0.8329 0.1167 0.019 Uiso 1 1 calc R . .
C13 C 0.7922(4) 0.5164(2) 0.27664(6) 0.0202(4) Uani 1 1 d . . .
H13A H 0.9099 0.5272 0.2529 0.030 Uiso 1 1 calc R . .
H13B H 0.8930 0.5076 0.3024 0.030 Uiso 1 1 calc R . .
H13C H 0.6790 0.5946 0.2787 0.030 Uiso 1 1 calc R . .
C10 C 0.7011(4) 0.1085(2) 0.02129(6) 0.0228(4) Uani 1 1 d . . .
H10A H 0.8658 0.1432 0.0319 0.034 Uiso 1 1 calc R . .
H10B H 0.6706 0.1429 -0.0069 0.034 Uiso 1 1 calc R . .
H10C H 0.7077 0.0108 0.0205 0.034 Uiso 1 1 calc R . .
H1 H 0.159(2) 0.433(2) 0.1810(6) 0.012(5) Uiso 1 1 d 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 C1 1.9070(18) . ?
S1 C8 1.8042(19) . ?
S1 C7 1.8324(18) . ?
O3 C9 1.203(2) . ?
C7 N1 1.4545(19) . ?
C7 C6 1.513(2) . ?
C7 H7 1.0000 . ?
O2 C11 1.350(2) . ?
O2 C12 1.485(2) . ?
N1 C11 1.350(2) . ?
N1 H1 0.893(9) . ?
O1 C11 1.219(2) . ?
O4 C9 1.337(2) . ?
O4 C10 1.452(2) . ?
C2 C1 1.382(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9500 . ?
C6 C5 1.398(2) . ?
C6 C1 1.401(2) . ?
C9 C8 1.511(3) . ?
C5 C4 1.388(3) . ?
C5 H5 0.9500 . ?
C15 C12 1.512(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 C14 1.521(2) . ?
C12 C13 1.523(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
C8 S1 C7 100.35(9) . . ?
N1 C7 C6 114.20(14) . . ?
N1 C7 S1 109.73(12) . . ?
C6 C7 S1 106.34(11) . . ?
N1 C7 H7 108.8 . . ?
C6 C7 H7 108.8 . . ?
S1 C7 H7 108.8 . . ?
C11 O2 C12 120.20(13) . . ?
C11 N1 C7 121.26(15) . . ?
C11 N1 H1 119.0(12) . . ?
C7 N1 H1 119.4(12) . . ?
C9 O4 C10 115.13(15) . . ?
C1 C2 C3 119.25(17) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
O1 C11 O2 125.67(16) . . ?
O1 C11 N1 124.44(15) . . ?
O2 C11 N1 109.89(15) . . ?
C5 C6 C1 117.12(17) . . ?
C5 C6 C7 120.92(16) . . ?
C1 C6 C7 121.87(16) . . ?
C2 C1 C6 122.30(17) . . ?
C2 C1 Br1 117.38(14) . . ?
C6 C1 Br1 120.32(14) . . ?
O3 C9 O4 123.85(17) . . ?
O3 C9 C8 123.34(16) . . ?
O4 C9 C8 112.75(16) . . ?
C4 C5 C6 121.50(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C12 C15 109.92(14) . . ?
O2 C12 C14 102.20(14) . . ?
C15 C12 C14 110.78(17) . . ?
O2 C12 C13 110.09(15) . . ?
C15 C12 C13 112.80(15) . . ?
C14 C12 C13 110.55(17) . . ?
C4 C3 C2 119.94(17) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C9 C8 S1 116.40(13) . . ?
C9 C8 H8A 108.2 . . ?
S1 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
S1 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 C3 119.86(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C8 S1 C7 N1 -70.82(13) . . . . ?
C8 S1 C7 C6 165.20(12) . . . . ?
C6 C7 N1 C11 -109.56(19) . . . . ?
S1 C7 N1 C11 131.17(15) . . . . ?
C12 O2 C11 O1 -5.5(3) . . . . ?
C12 O2 C11 N1 175.01(15) . . . . ?
C7 N1 C11 O1 8.3(3) . . . . ?
C7 N1 C11 O2 -172.22(15) . . . . ?
N1 C7 C6 C5 -32.5(2) . . . . ?
S1 C7 C6 C5 88.67(17) . . . . ?
N1 C7 C6 C1 151.14(17) . . . . ?
S1 C7 C6 C1 -87.70(18) . . . . ?
C3 C2 C1 C6 -0.7(3) . . . . ?
C3 C2 C1 Br1 178.97(14) . . . . ?
C5 C6 C1 C2 1.9(3) . . . . ?
C7 C6 C1 C2 178.41(17) . . . . ?
C5 C6 C1 Br1 -177.77(13) . . . . ?
C7 C6 C1 Br1 -1.3(2) . . . . ?
C10 O4 C9 O3 -2.1(3) . . . . ?
C10 O4 C9 C8 -179.19(16) . . . . ?
C1 C6 C5 C4 -1.8(3) . . . . ?
C7 C6 C5 C4 -178.31(17) . . . . ?
C11 O2 C12 C15 -60.7(2) . . . . ?
C11 O2 C12 C14 -178.40(18) . . . . ?
C11 O2 C12 C13 64.1(2) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
O3 C9 C8 S1 146.01(17) . . . . ?
O4 C9 C8 S1 -36.9(2) . . . . ?
C7 S1 C8 C9 -84.50(15) . . . . ?
C6 C5 C4 C3 0.5(3) . . . . ?
C2 C3 C4 C5 0.8(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
N1 H1 O1 0.893(9) 2.138(11) 2.993(2) 160.3(17) 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.084
