# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1529748'
_audit_update_record             
;
2017-01-26 deposited with the CCDC.
2017-02-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H26 Br N O3 S'
_chemical_formula_sum            'C19 H26 Br N O3 S'
_chemical_formula_weight         428.38
_chemical_absolute_configuration syn

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   'P 212121'

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                   8.949(3)
_cell_length_b                   14.797(4)
_cell_length_c                   15.706(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2079.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(1)
_cell_measurement_reflns_used    1807
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      17.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    2.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7694
_exptl_absorpt_correction_T_max  0.8458
_exptl_absorpt_process_details   'Bruker/Siemens SADABS V2.03'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(1)
_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_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17494
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_sigmaI/netI    0.0888
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         25.12
_reflns_number_total             3704
_reflns_number_gt                2641
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART V5.625'
_computing_cell_refinement       'Bruker SMART V5.625'
_computing_data_reduction        'Bruker SAINT V6.28A'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL  Rel. 6.12/V (Siemens, 1996)'
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'

_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)+(0.0000P)²+0.4033P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_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   0.000(14)
_refine_ls_number_reflns         3704
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001

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
C1 C 0.7535(4) 0.3936(3) 0.0342(3) 0.0460(10) Uani 1 1 d . . .
H1 H 0.7451 0.3364 0.0031 0.055 Uiso 1 1 calc R . .
C2 C 0.7309(5) 0.4696(3) -0.0272(3) 0.0623(12) Uani 1 1 d . . .
H2 H 0.7820 0.4680 -0.0787 0.075 Uiso 1 1 calc R . .
C3 C 0.6428(6) 0.5384(4) -0.0121(3) 0.0696(14) Uani 1 1 d . . .
H3 H 0.6363 0.5837 -0.0529 0.084 Uiso 1 1 calc R . .
C4 C 0.5533(6) 0.5480(3) 0.0663(3) 0.0647(13) Uani 1 1 d . . .
H4A H 0.4505 0.5315 0.0544 0.078 Uiso 1 1 calc R . .
H4B H 0.5545 0.6106 0.0844 0.078 Uiso 1 1 calc R . .
C5 C 0.6121(5) 0.4891(3) 0.1378(3) 0.0547(11) Uani 1 1 d . . .
H5A H 0.5396 0.4873 0.1836 0.066 Uiso 1 1 calc R . .
H5B H 0.7037 0.5150 0.1600 0.066 Uiso 1 1 calc R . .
C6 C 0.6427(4) 0.3928(3) 0.1066(3) 0.0449(10) Uani 1 1 d . . .
H6 H 0.5485 0.3694 0.0837 0.054 Uiso 1 1 calc R . .
C7 C 0.6869(4) 0.3315(3) 0.1804(3) 0.0456(10) Uani 1 1 d . . .
H7 H 0.7723 0.3599 0.2088 0.055 Uiso 1 1 calc R . .
C8 C 0.5646(5) 0.3221(3) 0.2459(3) 0.0485(11) Uani 1 1 d . . .
C9 C 0.5817(6) 0.3556(3) 0.3284(3) 0.0650(13) Uani 1 1 d . . .
H9 H 0.6686 0.3867 0.3426 0.078 Uiso 1 1 calc R . .
C10 C 0.4731(7) 0.3438(4) 0.3892(3) 0.0779(16) Uani 1 1 d . . .
H10 H 0.4878 0.3650 0.4443 0.094 Uiso 1 1 calc R . .
C11 C 0.3455(7) 0.3013(4) 0.3684(3) 0.0715(15) Uani 1 1 d . . .
Br1 Br 0.19438(9) 0.28407(6) 0.45162(5) 0.1271(4) Uani 1 1 d . . .
C12 C 0.3221(6) 0.2689(3) 0.2882(4) 0.0716(14) Uani 1 1 d . . .
H12 H 0.2329 0.2400 0.2748 0.086 Uiso 1 1 calc R . .
C13 C 0.4318(5) 0.2793(4) 0.2272(3) 0.0623(12) Uani 1 1 d . . .
H13 H 0.4158 0.2570 0.1726 0.075 Uiso 1 1 calc R . .
O1 O 0.9043(3) 0.3994(2) 0.07133(18) 0.0522(7) Uani 1 1 d . . .
C14 C 1.0180(5) 0.3711(3) 0.0232(3) 0.0563(12) Uani 1 1 d . . .
O2 O 1.0020(3) 0.3448(2) -0.0490(2) 0.0698(9) Uani 1 1 d . . .
C15 C 1.1622(5) 0.3757(4) 0.0682(3) 0.0777(16) Uani 1 1 d . . .
H15A H 1.2367 0.3437 0.0362 0.117 Uiso 1 1 calc R . .
H15B H 1.1522 0.3486 0.1235 0.117 Uiso 1 1 calc R . .
H15C H 1.1918 0.4377 0.0744 0.117 Uiso 1 1 calc R . .
N1 N 0.7349(4) 0.2421(2) 0.1528(2) 0.0515(9) Uani 1 1 d . . .
H1N H 0.680(6) 0.216(4) 0.120(3) 0.077 Uiso 1 1 d . . .
S1 S 0.90265(12) 0.20558(9) 0.17333(8) 0.0612(3) Uani 1 1 d . . .
O3 O 0.9790(5) 0.1820(3) 0.0928(3) 0.1059(16) Uani 1 1 d . . .
C16 C 0.8628(5) 0.0969(4) 0.2242(3) 0.0656(13) Uani 1 1 d . . .
C17 C 1.0137(7) 0.0577(4) 0.2465(4) 0.095(2) Uani 1 1 d . . .
H17A H 1.0004 0.0011 0.2754 0.143 Uiso 1 1 calc R . .
H17B H 1.0665 0.0989 0.2829 0.143 Uiso 1 1 calc R . .
H17C H 1.0701 0.0482 0.1953 0.143 Uiso 1 1 calc R . .
C18 C 0.7818(8) 0.0370(4) 0.1650(5) 0.123(3) Uani 1 1 d . . .
H18A H 0.7938 -0.0246 0.1827 0.184 Uiso 1 1 calc R . .
H18B H 0.8213 0.0444 0.1086 0.184 Uiso 1 1 calc R . .
H18C H 0.6776 0.0524 0.1652 0.184 Uiso 1 1 calc R . .
C19 C 0.7744(9) 0.1187(6) 0.3041(5) 0.134(3) Uani 1 1 d . . .
H19A H 0.6760 0.1385 0.2885 0.200 Uiso 1 1 calc R . .
H19B H 0.8241 0.1658 0.3352 0.200 Uiso 1 1 calc R . .
H19C H 0.7672 0.0657 0.3390 0.200 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
C1 O1 1.472(5) . ?
C1 C2 1.495(6) . ?
C1 C6 1.509(6) . ?
C2 C3 1.309(7) . ?
C3 C4 1.476(7) . ?
C4 C5 1.516(7) . ?
C5 C6 1.531(6) . ?
C6 C7 1.524(6) . ?
C7 N1 1.457(5) . ?
C7 C8 1.508(6) . ?
C8 C13 1.378(6) . ?
C8 C9 1.397(6) . ?
C9 C10 1.373(7) . ?
C10 C11 1.344(8) . ?
C11 C12 1.364(8) . ?
C11 Br1 1.897(5) . ?
C12 C13 1.381(6) . ?
O1 C14 1.335(5) . ?
C14 O2 1.208(5) . ?
C14 C15 1.474(6) . ?
N1 S1 1.628(4) . ?
S1 O3 1.479(4) . ?
S1 C16 1.831(5) . ?
C16 C18 1.475(8) . ?
C16 C17 1.510(7) . ?
C16 C19 1.517(8) . ?

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
O1 C1 C2 109.6(3) . . ?
O1 C1 C6 107.7(3) . . ?
C2 C1 C6 113.7(4) . . ?
C3 C2 C1 123.4(4) . . ?
C2 C3 C4 123.6(5) . . ?
C3 C4 C5 112.0(4) . . ?
C4 C5 C6 111.1(4) . . ?
C1 C6 C7 114.0(3) . . ?
C1 C6 C5 110.6(3) . . ?
C7 C6 C5 110.9(3) . . ?
N1 C7 C8 109.4(3) . . ?
N1 C7 C6 113.0(3) . . ?
C8 C7 C6 112.7(3) . . ?
C13 C8 C9 117.1(4) . . ?
C13 C8 C7 121.5(4) . . ?
C9 C8 C7 121.4(4) . . ?
C10 C9 C8 121.5(5) . . ?
C11 C10 C9 119.5(5) . . ?
C10 C11 C12 121.3(5) . . ?
C10 C11 Br1 120.1(4) . . ?
C12 C11 Br1 118.7(5) . . ?
C11 C12 C13 119.5(5) . . ?
C8 C13 C12 121.1(4) . . ?
C14 O1 C1 117.1(3) . . ?
O2 C14 O1 122.9(4) . . ?
O2 C14 C15 124.7(4) . . ?
O1 C14 C15 112.4(4) . . ?
C7 N1 S1 120.9(3) . . ?
O3 S1 N1 109.5(2) . . ?
O3 S1 C16 104.8(2) . . ?
N1 S1 C16 101.5(2) . . ?
C18 C16 C17 110.8(5) . . ?
C18 C16 C19 113.1(6) . . ?
C17 C16 C19 110.9(5) . . ?
C18 C16 S1 110.3(4) . . ?
C17 C16 S1 105.3(3) . . ?
C19 C16 S1 106.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.044
