# 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_40122ta
_database_code_depnum_ccdc_archive 'CCDC 1044727'
_audit_update_record             
;
2015-01-21 deposited with the CCDC.
2015-03-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Br N O5 S'
_chemical_formula_sum            'C18 H18 Br N O5 S'
_chemical_formula_weight         440.30
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 212121'
_symmetry_Int_Tables_number      19

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                   9.3617(2)
_cell_length_b                   13.1822(2)
_cell_length_c                   14.7459(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1819.76(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    4.417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2711
_exptl_absorpt_correction_T_max  0.6664
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_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            15133
_diffrn_reflns_av_R_equivalents  0.0812
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.50
_diffrn_reflns_theta_max         68.22
_reflns_number_total             3291
_reflns_number_gt                3148
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0300P)²+1.3358P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_number_reflns         3291
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
Br1 Br 0.26243(4) 0.07169(3) 0.98294(3) 0.03019(13) Uani 1 1 d . . .
S2 S 0.37033(9) -0.41686(7) 1.12862(6) 0.0233(2) Uani 1 1 d . . .
O4 O 0.7732(2) -0.19456(17) 1.22391(17) 0.0205(5) Uani 1 1 d . . .
O2 O 0.3694(3) -0.50649(19) 1.07700(19) 0.0295(6) Uani 1 1 d . . .
C13 C 0.4736(4) -0.0820(3) 1.0086(2) 0.0231(7) Uani 1 1 d . . .
H1 H 0.5014 -0.0674 0.9480 0.028 Uiso 1 1 calc R . .
C14 C 0.3945(4) -0.1233(3) 1.1865(3) 0.0234(8) Uani 1 1 d . . .
H2 H 0.3683 -0.1365 1.2476 0.028 Uiso 1 1 calc R . .
O5 O 0.7895(3) -0.35642(18) 1.17211(19) 0.0277(6) Uani 1 1 d . . .
C1 C 0.3369(4) -0.3964(3) 1.3827(3) 0.0295(9) Uani 1 1 d . . .
H3 H 0.2700 -0.4497 1.3917 0.035 Uiso 1 1 calc R . .
O1 O 0.3617(3) -0.4533(2) 1.23206(18) 0.0283(6) Uani 1 1 d . . .
O3 O 0.2650(3) -0.34086(19) 1.11561(18) 0.0278(6) Uani 1 1 d . . .
C8 C 0.7225(4) -0.2821(3) 1.1929(2) 0.0221(8) Uani 1 1 d . . .
C15 C 0.3661(4) -0.0270(3) 1.0502(3) 0.0228(8) Uani 1 1 d . . .
C9 C 0.9322(4) -0.1796(3) 1.2293(3) 0.0239(8) Uani 1 1 d . . .
C2 C 0.3997(4) -0.3820(3) 1.2981(3) 0.0263(9) Uani 1 1 d . . .
C10 C 0.9873(4) -0.1744(3) 1.1322(3) 0.0312(10) Uani 1 1 d . . .
H4 H 0.9779 -0.2411 1.1036 0.047 Uiso 1 1 calc R . .
H5 H 1.0881 -0.1541 1.1326 0.047 Uiso 1 1 calc R . .
H6 H 0.9315 -0.1244 1.0980 0.047 Uiso 1 1 calc R . .
C16 C 0.5401(4) -0.1588(3) 1.0570(3) 0.0227(8) Uani 1 1 d . . .
H7 H 0.6161 -0.1955 1.0297 0.027 Uiso 1 1 calc R . .
C17 C 0.4973(4) -0.1831(3) 1.1451(3) 0.0207(8) Uani 1 1 d . . .
N1 N 0.5269(3) -0.3660(2) 1.1230(2) 0.0213(7) Uani 1 1 d . . .
C3 C 0.5297(4) -0.2395(3) 1.3541(3) 0.0238(8) Uani 1 1 d . . .
H8 H 0.5952 -0.1853 1.3452 0.029 Uiso 1 1 calc R . .
C4 C 0.4949(4) -0.3023(3) 1.2817(3) 0.0236(8) Uani 1 1 d . . .
C7 C 0.5561(4) -0.2806(3) 1.1873(2) 0.0197(8) Uani 1 1 d . . .
C18 C 0.3287(4) -0.0437(3) 1.1394(3) 0.0244(8) Uani 1 1 d . . .
H9 H 0.2597 -0.0020 1.1683 0.029 Uiso 1 1 calc R . .
C5 C 0.3723(4) -0.3330(3) 1.4530(3) 0.0308(9) Uani 1 1 d . . .
H10 H 0.3301 -0.3425 1.5109 0.037 Uiso 1 1 calc R . .
C11 C 0.9441(4) -0.0767(3) 1.2760(3) 0.0272(8) Uani 1 1 d . . .
H11 H 0.9000 -0.0246 1.2378 0.041 Uiso 1 1 calc R . .
H12 H 1.0450 -0.0602 1.2856 0.041 Uiso 1 1 calc R . .
H13 H 0.8948 -0.0793 1.3346 0.041 Uiso 1 1 calc R . .
C6 C 0.4702(4) -0.2548(3) 1.4395(3) 0.0295(9) Uani 1 1 d . . .
H14 H 0.4963 -0.2120 1.4885 0.035 Uiso 1 1 calc R . .
C12 C 1.0000(4) -0.2610(3) 1.2867(3) 0.0360(11) Uani 1 1 d . . .
H15 H 0.9918 -0.3265 1.2558 0.054 Uiso 1 1 calc R . .
H16 H 0.9513 -0.2645 1.3454 0.054 Uiso 1 1 calc R . .
H17 H 1.1011 -0.2449 1.2962 0.054 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 C15 1.902(3) . ?
S2 O2 1.405(3) . ?
S2 O3 1.419(3) . ?
S2 O1 1.601(3) . ?
S2 N1 1.614(3) . ?
O4 C8 1.329(4) . ?
O4 C9 1.503(4) . ?
C13 C16 1.385(5) . ?
C13 C15 1.384(5) . ?
C13 H1 0.9500 . ?
C14 C17 1.385(5) . ?
C14 C18 1.402(5) . ?
C14 H2 0.9500 . ?
O5 C8 1.202(4) . ?
C1 C5 1.371(6) . ?
C1 C2 1.392(6) . ?
C1 H3 0.9500 . ?
O1 C2 1.400(5) . ?
C8 C7 1.560(5) . ?
C15 C18 1.379(5) . ?
C9 C12 1.507(5) . ?
C9 C11 1.525(5) . ?
C9 C10 1.524(6) . ?
C2 C4 1.399(5) . ?
C10 H4 0.9800 . ?
C10 H5 0.9800 . ?
C10 H6 0.9800 . ?
C16 C17 1.397(5) . ?
C16 H7 0.9500 . ?
C17 C7 1.530(5) . ?
N1 C7 1.497(4) . ?
C3 C4 1.389(5) . ?
C3 C6 1.391(5) . ?
C3 H8 0.9500 . ?
C4 C7 1.533(5) . ?
C18 H9 0.9500 . ?
C5 C6 1.393(6) . ?
C5 H10 0.9500 . ?
C11 H11 0.9800 . ?
C11 H12 0.9800 . ?
C11 H13 0.9800 . ?
C6 H14 0.9500 . ?
C12 H15 0.9800 . ?
C12 H16 0.9800 . ?
C12 H17 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 S2 O3 121.06(16) . . ?
O2 S2 O1 105.28(15) . . ?
O3 S2 O1 107.80(15) . . ?
O2 S2 N1 109.09(16) . . ?
O3 S2 N1 109.33(16) . . ?
O1 S2 N1 102.65(15) . . ?
C8 O4 C9 119.1(3) . . ?
C16 C13 C15 118.8(3) . . ?
C16 C13 H1 120.6 . . ?
C15 C13 H1 120.6 . . ?
C17 C14 C18 120.9(4) . . ?
C17 C14 H2 119.6 . . ?
C18 C14 H2 119.6 . . ?
C5 C1 C2 119.4(4) . . ?
C5 C1 H3 120.3 . . ?
C2 C1 H3 120.3 . . ?
C2 O1 S2 116.7(2) . . ?
O5 C8 O4 127.5(3) . . ?
O5 C8 C7 121.2(3) . . ?
O4 C8 C7 111.3(3) . . ?
C18 C15 C13 121.6(3) . . ?
C18 C15 Br1 118.5(3) . . ?
C13 C15 Br1 119.9(3) . . ?
O4 C9 C12 110.7(3) . . ?
O4 C9 C11 102.3(3) . . ?
C12 C9 C11 110.4(3) . . ?
O4 C9 C10 106.9(3) . . ?
C12 C9 C10 114.7(3) . . ?
C11 C9 C10 111.1(3) . . ?
C1 C2 O1 115.1(3) . . ?
C1 C2 C4 121.8(4) . . ?
O1 C2 C4 123.1(4) . . ?
C9 C10 H4 109.5 . . ?
C9 C10 H5 109.5 . . ?
H4 C10 H5 109.5 . . ?
C9 C10 H6 109.5 . . ?
H4 C10 H6 109.5 . . ?
H5 C10 H6 109.5 . . ?
C13 C16 C17 121.2(3) . . ?
C13 C16 H7 119.4 . . ?
C17 C16 H7 119.4 . . ?
C14 C17 C16 118.6(3) . . ?
C14 C17 C7 123.3(3) . . ?
C16 C17 C7 117.9(3) . . ?
C7 N1 S2 116.5(2) . . ?
C4 C3 C6 120.9(4) . . ?
C4 C3 H8 119.5 . . ?
C6 C3 H8 119.5 . . ?
C3 C4 C2 117.7(4) . . ?
C3 C4 C7 119.9(3) . . ?
C2 C4 C7 122.4(4) . . ?
N1 C7 C17 108.0(3) . . ?
N1 C7 C4 111.5(3) . . ?
C17 C7 C4 113.1(3) . . ?
N1 C7 C8 101.9(3) . . ?
C17 C7 C8 113.1(3) . . ?
C4 C7 C8 108.8(3) . . ?
C15 C18 C14 118.7(3) . . ?
C15 C18 H9 120.6 . . ?
C14 C18 H9 120.6 . . ?
C1 C5 C6 120.1(4) . . ?
C1 C5 H10 119.9 . . ?
C6 C5 H10 119.9 . . ?
C9 C11 H11 109.5 . . ?
C9 C11 H12 109.5 . . ?
H11 C11 H12 109.5 . . ?
C9 C11 H13 109.5 . . ?
H11 C11 H13 109.5 . . ?
H12 C11 H13 109.5 . . ?
C3 C6 C5 120.0(4) . . ?
C3 C6 H14 120.0 . . ?
C5 C6 H14 120.0 . . ?
C9 C12 H15 109.5 . . ?
C9 C12 H16 109.5 . . ?
H15 C12 H16 109.5 . . ?
C9 C12 H17 109.5 . . ?
H15 C12 H17 109.5 . . ?
H16 C12 H17 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 S2 O1 C2 163.1(2) . . . . ?
O3 S2 O1 C2 -66.4(3) . . . . ?
N1 S2 O1 C2 49.0(3) . . . . ?
C9 O4 C8 O5 4.5(6) . . . . ?
C9 O4 C8 C7 -176.7(3) . . . . ?
C16 C13 C15 C18 3.1(5) . . . . ?
C16 C13 C15 Br1 -175.1(3) . . . . ?
C8 O4 C9 C12 -56.9(4) . . . . ?
C8 O4 C9 C11 -174.6(3) . . . . ?
C8 O4 C9 C10 68.7(4) . . . . ?
C5 C1 C2 O1 177.1(3) . . . . ?
C5 C1 C2 C4 -2.1(6) . . . . ?
S2 O1 C2 C1 153.7(3) . . . . ?
S2 O1 C2 C4 -27.1(4) . . . . ?
C15 C13 C16 C17 2.1(5) . . . . ?
C18 C14 C17 C16 3.6(5) . . . . ?
C18 C14 C17 C7 -170.3(3) . . . . ?
C13 C16 C17 C14 -5.3(5) . . . . ?
C13 C16 C17 C7 168.9(3) . . . . ?
O2 S2 N1 C7 -169.1(2) . . . . ?
O3 S2 N1 C7 56.5(3) . . . . ?
O1 S2 N1 C7 -57.8(3) . . . . ?
C6 C3 C4 C2 -0.8(5) . . . . ?
C6 C3 C4 C7 176.9(3) . . . . ?
C1 C2 C4 C3 2.4(5) . . . . ?
O1 C2 C4 C3 -176.7(3) . . . . ?
C1 C2 C4 C7 -175.2(3) . . . . ?
O1 C2 C4 C7 5.6(5) . . . . ?
S2 N1 C7 C17 -83.6(3) . . . . ?
S2 N1 C7 C4 41.2(4) . . . . ?
S2 N1 C7 C8 157.1(2) . . . . ?
C14 C17 C7 N1 121.1(4) . . . . ?
C16 C17 C7 N1 -52.8(4) . . . . ?
C14 C17 C7 C4 -2.7(5) . . . . ?
C16 C17 C7 C4 -176.7(3) . . . . ?
C14 C17 C7 C8 -126.9(4) . . . . ?
C16 C17 C7 C8 59.1(4) . . . . ?
C3 C4 C7 N1 170.1(3) . . . . ?
C2 C4 C7 N1 -12.2(5) . . . . ?
C3 C4 C7 C17 -68.0(4) . . . . ?
C2 C4 C7 C17 109.6(4) . . . . ?
C3 C4 C7 C8 58.5(4) . . . . ?
C2 C4 C7 C8 -123.8(4) . . . . ?
O5 C8 C7 N1 -20.2(5) . . . . ?
O4 C8 C7 N1 160.9(3) . . . . ?
O5 C8 C7 C17 -135.9(4) . . . . ?
O4 C8 C7 C17 45.3(4) . . . . ?
O5 C8 C7 C4 97.6(4) . . . . ?
O4 C8 C7 C4 -81.3(4) . . . . ?
C13 C15 C18 C14 -4.7(5) . . . . ?
Br1 C15 C18 C14 173.5(3) . . . . ?
C17 C14 C18 C15 1.3(5) . . . . ?
C2 C1 C5 C6 0.1(6) . . . . ?
C4 C3 C6 C5 -1.1(5) . . . . ?
C1 C5 C6 C3 1.4(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.083


#-------------------------------------------------------------
#------------------------------------------------------------


