# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Br N3 O5 S2'
_chemical_formula_weight         476.36
_chemical_absolute_configuration ad

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           Monoclinic
_symmetry_space_group_name_H-M   'C2   '

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

_cell_length_a                   18.898(3)
_cell_length_b                   8.9379(15)
_cell_length_c                   13.094(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.023(11)
_cell_angle_gamma                90.00
_cell_volume                     2114.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'transparent yellow'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    2.171
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.5433
_exptl_absorpt_correction_T_max  0.7655
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6931
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0747
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3564
_reflns_number_gt                2866
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0214P)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    'riding mode'
_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   0.005(10)
_refine_ls_number_reflns         3564
_refine_ls_number_parameters     290
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.0975
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.997
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.89417(3) 0.14908(11) 1.45184(4) 0.1333(3) Uani 1 1 d . . .
S1 S 0.80082(5) 0.12720(13) 0.91575(9) 0.0722(3) Uani 1 1 d . . .
S2 S 0.64841(5) 0.04561(12) 0.79940(7) 0.0604(3) Uani 1 1 d . . .
O1 O 0.59688(12) -0.0374(3) 1.05651(17) 0.0564(6) Uani 1 1 d . . .
O2 O 0.57697(12) 0.2694(3) 0.93721(18) 0.0536(6) Uani 1 1 d . . .
O3 O 0.46027(13) 0.2939(3) 0.8272(2) 0.0568(6) Uani 1 1 d . . .
C1 C 0.71918(17) 0.0675(4) 0.9153(3) 0.0504(8) Uani 1 1 d . . .
C2 C 0.58175(17) -0.0203(4) 0.8682(3) 0.0481(8) Uani 1 1 d . . .
C3 C 0.62358(16) -0.0047(4) 0.9865(3) 0.0465(8) Uani 1 1 d . . .
C4 C 0.5623(2) -0.1823(4) 0.8449(3) 0.0657(10) Uani 1 1 d . . .
H4A H 0.5278 -0.2129 0.8820 0.099 Uiso 1 1 calc R . .
H4B H 0.6063 -0.2420 0.8683 0.099 Uiso 1 1 calc R . .
H4C H 0.5404 -0.1954 0.7695 0.099 Uiso 1 1 calc R . .
C5 C 0.52153(18) 0.2196(4) 0.8733(2) 0.0458(8) Uani 1 1 d . . .
C6 C 0.4605(2) 0.4552(5) 0.8448(3) 0.0672(11) Uani 1 1 d . . .
H6A H 0.5109 0.4927 0.8657 0.081 Uiso 1 1 calc R . .
H6B H 0.4387 0.4777 0.9015 0.081 Uiso 1 1 calc R . .
C7 C 0.4175(3) 0.5266(6) 0.7449(4) 0.0891(14) Uani 1 1 d . . .
H7A H 0.4169 0.6329 0.7550 0.134 Uiso 1 1 calc R . .
H7B H 0.3677 0.4891 0.7250 0.134 Uiso 1 1 calc R . .
H7C H 0.4397 0.5045 0.6895 0.134 Uiso 1 1 calc R . .
O4 O 0.4982(16) 0.100(2) 0.630(2) 0.076(4) Uani 0.389(16) 1 d PU A 1
O5 O 0.3797(15) 0.094(2) 0.6008(19) 0.081(3) Uani 0.389(16) 1 d PU A 1
C8 C 0.455(2) 0.085(8) 0.657(3) 0.075(4) Uani 0.389(16) 1 d PU A 1
C9 C 0.3665(11) 0.168(3) 0.4939(13) 0.090(3) Uani 0.389(16) 1 d PU A 1
H9A H 0.4070 0.2358 0.4969 0.108 Uiso 0.389(16) 1 calc PR A 1
H9B H 0.3662 0.0919 0.4408 0.108 Uiso 0.389(16) 1 calc PR A 1
C10 C 0.3198(13) 0.223(3) 0.4719(14) 0.119(5) Uani 0.389(16) 1 d PU A 1
H10A H 0.3131 0.2645 0.4020 0.178 Uiso 0.389(16) 1 calc PR A 1
H10B H 0.3210 0.3025 0.5217 0.178 Uiso 0.389(16) 1 calc PR A 1
H10C H 0.2796 0.1567 0.4702 0.178 Uiso 0.389(16) 1 calc PR A 1
O4' O 0.4984(10) 0.1593(17) 0.6412(13) 0.081(3) Uani 0.611(16) 1 d PU A 2
O5' O 0.3784(9) 0.0432(14) 0.6022(12) 0.083(3) Uani 0.611(16) 1 d PU A 2
C8' C 0.4453(11) 0.077(4) 0.6664(18) 0.068(3) Uani 0.611(16) 1 d PU A 2
C9' C 0.3615(6) 0.081(2) 0.4909(8) 0.091(3) Uani 0.611(16) 1 d PU A 2
H9'A H 0.3688 -0.0073 0.4521 0.109 Uiso 0.611(16) 1 calc PR A 2
H9'B H 0.3963 0.1563 0.4828 0.109 Uiso 0.611(16) 1 calc PR A 2
C10' C 0.2868(6) 0.137(2) 0.4423(7) 0.129(4) Uani 0.611(16) 1 d PU A 2
H10D H 0.2796 0.1550 0.3677 0.193 Uiso 0.611(16) 1 calc PR A 2
H10E H 0.2799 0.2282 0.4767 0.193 Uiso 0.611(16) 1 calc PR A 2
H10F H 0.2516 0.0637 0.4505 0.193 Uiso 0.611(16) 1 calc PR A 2
C11 C 0.74383(16) 0.0604(4) 1.1114(2) 0.0473(7) Uani 1 1 d . . .
C12 C 0.72573(18) 0.1735(5) 1.1706(3) 0.0554(9) Uani 1 1 d . . .
H12A H 0.6842 0.2325 1.1413 0.066 Uiso 1 1 calc R . .
C13 C 0.7693(2) 0.1986(5) 1.2729(3) 0.0710(11) Uani 1 1 d . . .
H13A H 0.7577 0.2740 1.3142 0.085 Uiso 1 1 calc R . .
C14 C 0.8308(2) 0.1099(5) 1.3134(3) 0.0692(12) Uani 1 1 d . . .
C15 C 0.8488(2) -0.0039(6) 1.2553(3) 0.0746(12) Uani 1 1 d . . .
H15A H 0.8902 -0.0633 1.2850 0.089 Uiso 1 1 calc R . .
C16 C 0.80500(18) -0.0295(4) 1.1523(3) 0.0586(9) Uani 1 1 d . . .
H16A H 0.8164 -0.1056 1.1113 0.070 Uiso 1 1 calc R . .
N1 N 0.69679(13) 0.0358(3) 1.0044(2) 0.0471(6) Uani 1 1 d . . .
N2 N 0.51535(13) 0.0727(3) 0.84259(19) 0.0448(6) Uani 1 1 d . A .
N3 N 0.45418(15) 0.0269(4) 0.7612(2) 0.0543(7) Uani 1 1 d . . .
H3A H 0.4286 -0.0548 0.7695 0.065 Uiso 1 1 d R A .


_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 C14 1.890(3) . ?
S1 C1 1.631(3) . ?
S2 C1 1.715(3) . ?
S2 C2 1.847(3) . ?
O1 C3 1.204(4) . ?
O2 C5 1.218(4) . ?
O3 C5 1.318(4) . ?
O3 C6 1.460(5) . ?
C1 N1 1.382(4) . ?
C2 N2 1.460(4) . ?
C2 C4 1.503(5) . ?
C2 C3 1.525(5) . ?
C3 N1 1.382(4) . ?
C5 N2 1.368(4) . ?
C6 C7 1.468(6) . ?
O4 C8 1.00(5) . ?
O5 C8 1.39(4) . ?
O5 C9 1.50(3) . ?
C8 N3 1.47(4) . ?
C9 C10 0.98(3) . ?
O4' C8' 1.36(4) . ?
O5' C8' 1.33(2) . ?
O5' C9' 1.437(16) . ?
C8' N3 1.29(2) . ?
C9' C10' 1.456(16) . ?
C11 C12 1.376(5) . ?
C11 C16 1.381(5) . ?
C11 N1 1.440(4) . ?
C12 C13 1.371(5) . ?
C13 C14 1.377(6) . ?
C14 C15 1.373(6) . ?
C15 C16 1.379(5) . ?
N2 N3 1.385(4) . ?

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
C1 S2 C2 94.08(15) . . ?
C5 O3 C6 117.6(3) . . ?
N1 C1 S1 126.0(2) . . ?
N1 C1 S2 111.8(2) . . ?
S1 C1 S2 122.2(2) . . ?
N2 C2 C4 111.1(3) . . ?
N2 C2 C3 109.7(3) . . ?
C4 C2 C3 108.5(3) . . ?
N2 C2 S2 111.7(2) . . ?
C4 C2 S2 111.7(3) . . ?
C3 C2 S2 104.0(2) . . ?
O1 C3 N1 123.8(3) . . ?
O1 C3 C2 122.9(3) . . ?
N1 C3 C2 113.1(3) . . ?
O2 C5 O3 126.5(3) . . ?
O2 C5 N2 122.3(3) . . ?
O3 C5 N2 111.2(3) . . ?
O3 C6 C7 108.3(4) . . ?
C8 O5 C9 112(2) . . ?
O4 C8 O5 129(4) . . ?
O4 C8 N3 127(4) . . ?
O5 C8 N3 103(2) . . ?
C10 C9 O5 112.8(19) . . ?
C8' O5' C9' 118.3(13) . . ?
N3 C8' O4' 121.8(19) . . ?
N3 C8' O5' 111.2(16) . . ?
O4' C8' O5' 127.0(18) . . ?
O5' C9' C10' 115.0(9) . . ?
C12 C11 C16 121.8(3) . . ?
C12 C11 N1 118.4(3) . . ?
C16 C11 N1 119.8(3) . . ?
C13 C12 C11 119.5(4) . . ?
C12 C13 C14 118.7(4) . . ?
C13 C14 C15 122.1(3) . . ?
C13 C14 Br1 119.3(3) . . ?
C15 C14 Br1 118.6(3) . . ?
C16 C15 C14 119.3(4) . . ?
C15 C16 C11 118.5(4) . . ?
C1 N1 C3 116.7(3) . . ?
C1 N1 C11 122.4(3) . . ?
C3 N1 C11 120.5(3) . . ?
C5 N2 N3 119.3(3) . . ?
C5 N2 C2 119.0(3) . . ?
N3 N2 C2 118.4(3) . . ?
C8' N3 N2 118.9(13) . . ?
C8' N3 C8 7(2) . . ?
N2 N3 C8 112.5(19) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.044
_database_code_depnum_ccdc_archive 'CCDC 1016301'
