# 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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
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data_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Br3 N O3 S'
_chemical_formula_sum            'C18 H18 Br3 N O3 S'
_chemical_formula_weight         568.12

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   'P 21/n'
_symmetry_space_group_name_HALL  '-P 2yn'

loop_
_symmetry_equiv_pos_as_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                   10.212(3)
_cell_length_b                   11.258(3)
_cell_length_c                   17.747(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.985(4)
_cell_angle_gamma                90.00
_cell_volume                     2015.3(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3180
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      25.3

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.872
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    6.127
_exptl_absorpt_correction_type   Numerical
_exptl_absorpt_correction_T_min  0.277
_exptl_absorpt_correction_T_max  0.522
_exptl_absorpt_process_details   
; 
Rigaku CrystalClear-SM Expert 2.1 b24 
;

_exptl_special_details           
; 
? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_device_type  
; 
Rigaku CrystalClear-SM Expert 2.1 b24 
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15300
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_sigmaI/netI    0.0591
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         25.34
_reflns_number_total             3677
_reflns_number_gt                2982
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012) 
;
_computing_cell_refinement       
; 
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012) 
;
_computing_data_reduction        
; 
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0198P)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_number_reflns         3677
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0584
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_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 1.21536(3) 0.26182(2) 0.66288(2) 0.02157(10) Uani 1 1 d . . .
Br2 Br 1.21466(3) 0.15643(2) 0.49759(2) 0.02162(10) Uani 1 1 d . . .
Br3 Br 1.11929(3) -0.00156(2) 0.62410(2) 0.02024(10) Uani 1 1 d . . .
S1 S 0.84471(8) 0.36223(6) 0.46677(5) 0.01408(18) Uani 1 1 d . . .
O1 O 0.8884(2) 0.46292(15) 0.42694(13) 0.0169(5) Uani 1 1 d . . .
O2 O 0.7874(2) 0.26201(15) 0.42399(13) 0.0166(5) Uani 1 1 d . . .
O3 O 0.6122(2) -0.02648(17) 0.65290(15) 0.0255(6) Uani 1 1 d . . .
N1 N 0.9775(3) 0.3152(2) 0.52170(17) 0.0156(6) Uani 1 1 d . . .
H1 H 1.020(3) 0.366(2) 0.544(2) 0.014(9) Uiso 1 1 d . . .
C1 C 1.1202(3) 0.1589(2) 0.5846(2) 0.0164(7) Uani 1 1 d . . .
C2 C 0.9760(3) 0.2009(2) 0.56099(19) 0.0143(7) Uani 1 1 d . . .
H2A H 0.9304 0.1421 0.5235 0.017 Uiso 1 1 calc R . .
C3 C 0.9000(3) 0.2072(2) 0.62670(19) 0.0154(7) Uani 1 1 d . . .
H3A H 0.9321 0.2582 0.6681 0.019 Uiso 1 1 calc R . .
C4 C 0.7905(3) 0.1455(2) 0.6303(2) 0.0170(7) Uani 1 1 d . . .
H4A H 0.7671 0.0859 0.5927 0.020 Uiso 1 1 calc R . .
C5 C 0.7022(3) 0.1617(2) 0.68752(19) 0.0167(7) Uani 1 1 d . . .
C6 C 0.7023(3) 0.2644(2) 0.7301(2) 0.0190(8) Uani 1 1 d . . .
H6A H 0.7644 0.3251 0.7241 0.023 Uiso 1 1 calc R . .
C7 C 0.6153(3) 0.2815(3) 0.7811(2) 0.0242(8) Uani 1 1 d . . .
H7A H 0.6184 0.3526 0.8101 0.029 Uiso 1 1 calc R . .
C8 C 0.5233(3) 0.1943(3) 0.7898(2) 0.0283(9) Uani 1 1 d . . .
H8A H 0.4625 0.2060 0.8245 0.034 Uiso 1 1 calc R . .
C9 C 0.5194(3) 0.0904(3) 0.7483(2) 0.0259(8) Uani 1 1 d . . .
H9A H 0.4567 0.0305 0.7548 0.031 Uiso 1 1 calc R . .
C10 C 0.6073(3) 0.0736(2) 0.6969(2) 0.0205(8) Uani 1 1 d . . .
C11 C 0.5035(3) -0.1082(3) 0.6480(2) 0.0332(9) Uani 1 1 d . . .
H11A H 0.5148 -0.1711 0.6114 0.050 Uiso 1 1 calc R . .
H11B H 0.4202 -0.0659 0.6310 0.050 Uiso 1 1 calc R . .
H11C H 0.5011 -0.1434 0.6983 0.050 Uiso 1 1 calc R . .
C12 C 0.7309(3) 0.4144(2) 0.52486(18) 0.0130(7) Uani 1 1 d . . .
C13 C 0.6147(3) 0.3526(2) 0.52764(19) 0.0151(7) Uani 1 1 d . . .
H13A H 0.5944 0.2831 0.4978 0.018 Uiso 1 1 calc R . .
C14 C 0.5279(3) 0.3937(2) 0.57478(18) 0.0155(7) Uani 1 1 d . . .
H14A H 0.4480 0.3515 0.5770 0.019 Uiso 1 1 calc R . .
C15 C 0.5558(3) 0.4953(2) 0.61882(19) 0.0152(7) Uani 1 1 d . . .
C16 C 0.6740(3) 0.5560(2) 0.61383(19) 0.0165(7) Uani 1 1 d . . .
H16A H 0.6945 0.6260 0.6432 0.020 Uiso 1 1 calc R . .
C17 C 0.7612(3) 0.5166(2) 0.56727(19) 0.0163(7) Uani 1 1 d . . .
H17A H 0.8407 0.5590 0.5644 0.020 Uiso 1 1 calc R . .
C18 C 0.4647(3) 0.5389(3) 0.6713(2) 0.0213(8) Uani 1 1 d . . .
H18A H 0.5121 0.5405 0.7237 0.032 Uiso 1 1 calc R . .
H18B H 0.3882 0.4856 0.6683 0.032 Uiso 1 1 calc R . .
H18C H 0.4341 0.6192 0.6561 0.032 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
Br1 C1 1.948(3) . ?
Br2 C1 1.945(3) . ?
Br3 C1 1.938(3) . ?
S1 O2 1.433(2) . ?
S1 O1 1.443(2) . ?
S1 N1 1.630(3) . ?
S1 C12 1.770(3) . ?
O3 C10 1.376(4) . ?
O3 C11 1.434(3) . ?
N1 C2 1.465(4) . ?
N1 H1 0.78(3) . ?
C1 C2 1.541(4) . ?
C2 C3 1.500(4) . ?
C2 H2A 1.0000 . ?
C3 C4 1.326(4) . ?
C3 H3A 0.9500 . ?
C4 C5 1.471(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.382(4) . ?
C5 C10 1.414(4) . ?
C6 C7 1.376(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.384(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.379(5) . ?
C8 H8A 0.9500 . ?
C9 C10 1.388(4) . ?
C9 H9A 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.383(4) . ?
C12 C17 1.384(4) . ?
C13 C14 1.389(4) . ?
C13 H13A 0.9500 . ?
C14 C15 1.389(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.402(4) . ?
C15 C18 1.498(4) . ?
C16 C17 1.379(4) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O2 S1 O1 119.40(13) . . ?
O2 S1 N1 107.11(13) . . ?
O1 S1 N1 104.84(13) . . ?
O2 S1 C12 108.58(13) . . ?
O1 S1 C12 107.82(12) . . ?
N1 S1 C12 108.67(15) . . ?
C10 O3 C11 117.6(2) . . ?
C2 N1 S1 120.0(2) . . ?
C2 N1 H1 117(2) . . ?
S1 N1 H1 114(2) . . ?
C2 C1 Br3 109.03(19) . . ?
C2 C1 Br2 111.1(2) . . ?
Br3 C1 Br2 107.74(13) . . ?
C2 C1 Br1 111.15(19) . . ?
Br3 C1 Br1 109.06(17) . . ?
Br2 C1 Br1 108.70(14) . . ?
N1 C2 C3 112.0(2) . . ?
N1 C2 C1 108.5(2) . . ?
C3 C2 C1 113.0(3) . . ?
N1 C2 H2A 107.7 . . ?
C3 C2 H2A 107.7 . . ?
C1 C2 H2A 107.7 . . ?
C4 C3 C2 123.7(3) . . ?
C4 C3 H3A 118.2 . . ?
C2 C3 H3A 118.2 . . ?
C3 C4 C5 125.5(3) . . ?
C3 C4 H4A 117.3 . . ?
C5 C4 H4A 117.3 . . ?
C6 C5 C10 117.6(3) . . ?
C6 C5 C4 122.2(3) . . ?
C10 C5 C4 120.0(3) . . ?
C7 C6 C5 122.1(3) . . ?
C7 C6 H6A 119.0 . . ?
C5 C6 H6A 119.0 . . ?
C6 C7 C8 119.6(3) . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 H7A 120.2 . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8A 119.8 . . ?
C7 C8 H8A 119.8 . . ?
C8 C9 C10 119.9(3) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
O3 C10 C9 124.6(3) . . ?
O3 C10 C5 114.9(3) . . ?
C9 C10 C5 120.5(3) . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 121.3(3) . . ?
C13 C12 S1 119.9(2) . . ?
C17 C12 S1 118.8(2) . . ?
C12 C13 C14 119.0(3) . . ?
C12 C13 H13A 120.5 . . ?
C14 C13 H13A 120.5 . . ?
C13 C14 C15 121.3(3) . . ?
C13 C14 H14A 119.4 . . ?
C15 C14 H14A 119.4 . . ?
C14 C15 C16 117.9(3) . . ?
C14 C15 C18 121.8(3) . . ?
C16 C15 C18 120.3(3) . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16A 119.2 . . ?
C15 C16 H16A 119.2 . . ?
C16 C17 C12 118.9(3) . . ?
C16 C17 H17A 120.6 . . ?
C12 C17 H17A 120.6 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C2 -41.4(3) . . . . ?
O1 S1 N1 C2 -169.2(2) . . . . ?
C12 S1 N1 C2 75.7(2) . . . . ?
S1 N1 C2 C3 -74.1(3) . . . . ?
S1 N1 C2 C1 160.5(2) . . . . ?
Br3 C1 C2 N1 -172.3(2) . . . . ?
Br2 C1 C2 N1 -53.7(3) . . . . ?
Br1 C1 C2 N1 67.4(3) . . . . ?
Br3 C1 C2 C3 62.9(3) . . . . ?
Br2 C1 C2 C3 -178.56(17) . . . . ?
Br1 C1 C2 C3 -57.4(3) . . . . ?
N1 C2 C3 C4 116.7(3) . . . . ?
C1 C2 C3 C4 -120.3(3) . . . . ?
C2 C3 C4 C5 -170.4(3) . . . . ?
C3 C4 C5 C6 19.3(5) . . . . ?
C3 C4 C5 C10 -164.9(3) . . . . ?
C10 C5 C6 C7 0.9(5) . . . . ?
C4 C5 C6 C7 176.9(3) . . . . ?
C5 C6 C7 C8 -0.8(5) . . . . ?
C6 C7 C8 C9 0.6(5) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C11 O3 C10 C9 13.1(5) . . . . ?
C11 O3 C10 C5 -167.8(3) . . . . ?
C8 C9 C10 O3 179.8(3) . . . . ?
C8 C9 C10 C5 0.8(5) . . . . ?
C6 C5 C10 O3 179.9(3) . . . . ?
C4 C5 C10 O3 3.9(4) . . . . ?
C6 C5 C10 C9 -1.0(5) . . . . ?
C4 C5 C10 C9 -177.0(3) . . . . ?
O2 S1 C12 C13 5.2(3) . . . . ?
O1 S1 C12 C13 135.9(3) . . . . ?
N1 S1 C12 C13 -111.0(3) . . . . ?
O2 S1 C12 C17 -175.3(2) . . . . ?
O1 S1 C12 C17 -44.6(3) . . . . ?
N1 S1 C12 C17 68.5(3) . . . . ?
C17 C12 C13 C14 -0.8(5) . . . . ?
S1 C12 C13 C14 178.7(2) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 0.5(5) . . . . ?
C13 C14 C15 C18 -178.5(3) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C18 C15 C16 C17 178.6(3) . . . . ?
C15 C16 C17 C12 -0.3(5) . . . . ?
C13 C12 C17 C16 0.9(5) . . . . ?
S1 C12 C17 C16 -178.6(2) . . . . ?

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 0.78(3) 2.17(3) 2.925(3) 162(3) 3_766

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.711
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.113
_database_code_depnum_ccdc_archive 'CCDC 984737'
