# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_20170314cz_0m_b
_audit_block_doi                 10.5517/ccdc.csd.cc1nq31j
_database_code_depnum_ccdc_archive 'CCDC 1540577'
_audit_update_record             
;
2017-03-28 deposited with the CCDC.
2017-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H28 Br N O3 S'
_chemical_formula_weight         526.47

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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.2079(18)
_cell_length_b                   10.4253(16)
_cell_length_c                   11.4032(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.286(6)
_cell_angle_gamma                90
_cell_volume                     1203.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5243
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      27.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.824
_shelx_estimated_absorpt_T_min   0.648
_shelx_estimated_absorpt_T_max   0.690
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8311
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.657
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_full        25.003
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4132
_reflns_number_gt                3752
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.941

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_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-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1511 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.092(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4132
_refine_ls_number_parameters     299
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0978
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.48537(5) 0.54450(6) 0.44579(4) 0.02417(18) Uani 1 1 d . . . . .
C1 C 0.7034(7) 0.1487(6) 0.2372(6) 0.0285(15) Uani 1 1 d . . . . .
H1 H 0.7952 0.1502 0.2494 0.034 Uiso 1 1 calc R U . . .
C2 C 0.6400(7) 0.0563(7) 0.1638(5) 0.0302(14) Uani 1 1 d . . . . .
H2 H 0.6886 -0.0029 0.1262 0.036 Uiso 1 1 calc R U . . .
C3 C 0.5027(7) 0.0530(7) 0.1469(5) 0.0308(15) Uani 1 1 d . . . . .
H3 H 0.4592 -0.0083 0.0970 0.037 Uiso 1 1 calc R U . . .
C4 C 0.4314(7) 0.1394(6) 0.2033(6) 0.0308(16) Uani 1 1 d . . . . .
H4 H 0.3396 0.1362 0.1926 0.037 Uiso 1 1 calc R U . . .
C5 C 0.4962(7) 0.2309(5) 0.2760(6) 0.0275(15) Uani 1 1 d . . . . .
H5 H 0.4468 0.2885 0.3146 0.033 Uiso 1 1 calc R U . . .
C6 C 0.6328(6) 0.2399(5) 0.2934(5) 0.0207(14) Uani 1 1 d . . . . .
C7 C 0.7063(7) 0.3411(6) 0.3706(6) 0.0243(16) Uani 1 1 d . . . . .
H7A H 0.7974 0.3137 0.3892 0.029 Uiso 1 1 calc R U . . .
H7B H 0.6685 0.3453 0.4444 0.029 Uiso 1 1 calc R U . . .
C8 C 0.7057(6) 0.4793(5) 0.3172(5) 0.0195(13) Uani 1 1 d . . . . .
C9 C 0.7522(7) 0.4737(6) 0.1940(6) 0.0247(15) Uani 1 1 d . . . . .
H9A H 0.8414 0.4396 0.2022 0.030 Uiso 1 1 calc R U . . .
H9B H 0.6960 0.4144 0.1451 0.030 Uiso 1 1 calc R U . . .
C10 C 0.5690(5) 0.5419(7) 0.2982(4) 0.0178(11) Uani 1 1 d . . . . .
H10 H 0.5127 0.4918 0.2389 0.021 Uiso 1 1 calc R U . . .
C11 C 0.5796(6) 0.6803(5) 0.2506(5) 0.0173(13) Uani 1 1 d . . . . .
C12 C 0.4417(6) 0.7402(5) 0.2231(5) 0.0186(13) Uani 1 1 d . . . . .
C13 C 0.3691(7) 0.7160(6) 0.1127(5) 0.0259(15) Uani 1 1 d . . . . .
H13 H 0.4058 0.6667 0.0572 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2428(7) 0.7652(6) 0.0858(6) 0.0304(16) Uani 1 1 d . . . . .
H14 H 0.1964 0.7498 0.0115 0.036 Uiso 1 1 calc R U . . .
C15 C 0.1846(7) 0.8366(6) 0.1670(6) 0.0282(15) Uani 1 1 d . . . . .
H15 H 0.0994 0.8684 0.1487 0.034 Uiso 1 1 calc R U . . .
C16 C 0.2565(7) 0.8599(6) 0.2768(6) 0.0281(15) Uani 1 1 d . . . . .
H16 H 0.2188 0.9069 0.3332 0.034 Uiso 1 1 calc R U . . .
C17 C 0.3847(7) 0.8132(5) 0.3025(5) 0.0236(14) Uani 1 1 d . . . . .
H17 H 0.4327 0.8320 0.3753 0.028 Uiso 1 1 calc R U . . .
C18 C 0.7509(7) 0.6021(6) 0.1309(6) 0.0244(14) Uani 1 1 d . . . . .
H18A H 0.8248 0.6536 0.1661 0.029 Uiso 1 1 calc R U . . .
H18B H 0.7612 0.5882 0.0485 0.029 Uiso 1 1 calc R U . . .
C19 C 0.9001(6) 0.8116(5) 0.5724(5) 0.0213(13) Uani 1 1 d . . . . .
C20 C 0.9337(7) 0.7159(6) 0.6575(6) 0.0278(15) Uani 1 1 d . . . . .
H20 H 0.9691 0.6383 0.6365 0.033 Uiso 1 1 calc R U . . .
C21 C 0.9133(7) 0.7391(6) 0.7727(6) 0.0306(16) Uani 1 1 d . . . . .
H21 H 0.9331 0.6751 0.8290 0.037 Uiso 1 1 calc R U . . .
C22 C 0.8634(7) 0.8566(6) 0.8072(6) 0.0322(16) Uani 1 1 d . . . . .
C23 C 0.8323(7) 0.9507(6) 0.7200(6) 0.0321(16) Uani 1 1 d . . . . .
H23 H 0.7992 1.0296 0.7406 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8502(6) 0.9271(6) 0.6048(6) 0.0266(15) Uani 1 1 d . . . . .
H24 H 0.8284 0.9900 0.5478 0.032 Uiso 1 1 calc R U . . .
C25 C 0.8402(9) 0.8810(8) 0.9333(6) 0.048(2) Uani 1 1 d . . . . .
H25A H 0.7515 0.8569 0.9433 0.071 Uiso 1 1 calc R U . . .
H25B H 0.8530 0.9704 0.9513 0.071 Uiso 1 1 calc R U . . .
H25C H 0.9013 0.8311 0.9857 0.071 Uiso 1 1 calc R U . . .
C26 C 0.6734(6) 0.7596(6) 0.3396(6) 0.0216(15) Uani 1 1 d . . . . .
H26A H 0.6856 0.8441 0.3071 0.026 Uiso 1 1 calc R U . . .
H26B H 0.6344 0.7700 0.4123 0.026 Uiso 1 1 calc R U . . .
C27 C 0.7980(6) 0.5604(6) 0.4048(5) 0.0215(13) Uani 1 1 d . . . . .
H27A H 0.7678 0.5572 0.4821 0.026 Uiso 1 1 calc R U . . .
H27B H 0.8865 0.5249 0.4120 0.026 Uiso 1 1 calc R U . . .
N1 N 0.8009(5) 0.6958(4) 0.3648(4) 0.0225(12) Uani 1 1 d . . . . .
O1 O 0.9183(5) 0.9029(4) 0.3623(4) 0.0298(11) Uani 1 1 d . . . . .
O2 O 1.0417(4) 0.7045(4) 0.4265(4) 0.0280(10) Uani 1 1 d . . . . .
O3 O 0.6284(4) 0.6709(4) 0.1386(4) 0.0249(10) Uani 1 1 d . . . . .
S1 S 0.92577(16) 0.78254(13) 0.42417(13) 0.0224(3) Uani 1 1 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 C10 1.982(5) . ?
C1 C2 1.381(9) . ?
C1 C6 1.397(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.391(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(9) . ?
C5 H5 0.9300 . ?
C6 C7 1.512(8) . ?
C7 C8 1.564(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C10 1.530(8) . ?
C8 C27 1.536(7) . ?
C8 C9 1.541(9) . ?
C9 C18 1.520(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.550(8) . ?
C10 H10 0.9800 . ?
C11 O3 1.432(7) . ?
C11 C12 1.536(8) . ?
C11 C26 1.544(8) . ?
C12 C17 1.368(9) . ?
C12 C13 1.400(7) . ?
C13 C14 1.385(9) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(9) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O3 1.454(8) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C24 1.376(9) . ?
C19 C20 1.404(9) . ?
C19 S1 1.769(6) . ?
C20 C21 1.377(10) . ?
C20 H20 0.9300 . ?
C21 C22 1.402(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.404(9) . ?
C22 C25 1.509(10) . ?
C23 C24 1.372(10) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 N1 1.458(8) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 N1 1.485(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
N1 S1 1.638(5) . ?
O1 S1 1.437(4) . ?
O2 S1 1.434(5) . ?

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
C2 C1 C6 121.5(6) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 119.2(7) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.3(6) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.7(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 122.1(7) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 117.2(5) . . ?
C5 C6 C7 123.1(6) . . ?
C1 C6 C7 119.7(6) . . ?
C6 C7 C8 116.1(5) . . ?
C6 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C10 C8 C27 109.3(5) . . ?
C10 C8 C9 105.5(4) . . ?
C27 C8 C9 112.3(5) . . ?
C10 C8 C7 114.0(6) . . ?
C27 C8 C7 106.4(4) . . ?
C9 C8 C7 109.4(5) . . ?
C18 C9 C8 114.4(5) . . ?
C18 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C18 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C8 C10 C11 110.1(5) . . ?
C8 C10 Br1 111.6(3) . . ?
C11 C10 Br1 109.9(4) . . ?
C8 C10 H10 108.4 . . ?
C11 C10 H10 108.4 . . ?
Br1 C10 H10 108.4 . . ?
O3 C11 C12 105.0(4) . . ?
O3 C11 C26 111.5(5) . . ?
C12 C11 C26 113.1(5) . . ?
O3 C11 C10 107.3(4) . . ?
C12 C11 C10 110.3(5) . . ?
C26 C11 C10 109.5(4) . . ?
C17 C12 C13 118.3(6) . . ?
C17 C12 C11 123.1(5) . . ?
C13 C12 C11 118.5(5) . . ?
C14 C13 C12 120.3(6) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 121.2(6) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C14 C15 C16 118.4(6) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 121.5(5) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
O3 C18 C9 111.2(6) . . ?
O3 C18 H18A 109.4 . . ?
C9 C18 H18A 109.4 . . ?
O3 C18 H18B 109.4 . . ?
C9 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
C24 C19 C20 120.2(6) . . ?
C24 C19 S1 120.7(5) . . ?
C20 C19 S1 119.1(5) . . ?
C21 C20 C19 118.8(6) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 121.7(6) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C23 118.0(6) . . ?
C21 C22 C25 121.4(7) . . ?
C23 C22 C25 120.5(6) . . ?
C24 C23 C22 120.5(6) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.8(6) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C26 C11 110.4(5) . . ?
N1 C26 H26A 109.6 . . ?
C11 C26 H26A 109.6 . . ?
N1 C26 H26B 109.6 . . ?
C11 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
N1 C27 C8 111.0(4) . . ?
N1 C27 H27A 109.4 . . ?
C8 C27 H27A 109.4 . . ?
N1 C27 H27B 109.4 . . ?
C8 C27 H27B 109.4 . . ?
H27A C27 H27B 108.0 . . ?
C26 N1 C27 116.2(5) . . ?
C26 N1 S1 117.3(4) . . ?
C27 N1 S1 116.3(4) . . ?
C11 O3 C18 119.1(4) . . ?
O2 S1 O1 119.8(3) . . ?
O2 S1 N1 106.9(3) . . ?
O1 S1 N1 106.8(3) . . ?
O2 S1 C19 107.5(3) . . ?
O1 S1 C19 108.3(3) . . ?
N1 S1 C19 106.7(3) . . ?

_refine_diff_density_max         0.356
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.085

