# 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_mo_70227a
_audit_block_doi                 10.5517/ccdc.csd.cc1nlrtt
_database_code_depnum_ccdc_archive 'CCDC 1537377'
_audit_update_record             
;
2017-03-11 deposited with the CCDC.
2017-11-01 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            'C28 H18 Br2 N4 O3 S'
_chemical_formula_weight         650.34

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.854(3)
_cell_length_b                   13.770(4)
_cell_length_c                   18.821(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.928(6)
_cell_angle_gamma                90
_cell_volume                     2553.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    4021
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.96

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.296
_shelx_estimated_absorpt_T_min   0.290
_shelx_estimated_absorpt_T_max   0.559
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.411
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(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            14521
_diffrn_reflns_av_unetI/netI     0.0889
_diffrn_reflns_av_R_equivalents  0.0795
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             4931
_reflns_number_gt                2886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2014/7 (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)+(0.1658P)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_number_reflns         4931
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0785
_refine_ls_wR_factor_ref         0.2532
_refine_ls_wR_factor_gt          0.2129
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.006
_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_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 0.64021(9) -0.48721(7) 0.23128(5) 0.0680(4) Uani 1 1 d . . . . .
Br2 Br -0.70531(11) 0.10013(10) 0.59000(6) 0.1024(5) Uani 1 1 d . . . . .
S1 S -0.27456(17) 0.38077(12) 0.44792(9) 0.0390(4) Uani 1 1 d . . . . .
O1 O -0.3407(5) 0.4713(3) 0.4316(3) 0.0495(12) Uani 1 1 d . . . . .
O2 O -0.2043(5) 0.3313(4) 0.3926(2) 0.0479(12) Uani 1 1 d . . . . .
O3 O -0.0926(5) 0.1798(4) 0.5046(3) 0.0626(15) Uani 1 1 d . . . . .
N1 N 0.0898(5) 0.2487(4) 0.4518(3) 0.0423(13) Uani 1 1 d . . . . .
H1 H 0.1309 0.3042 0.4469 0.051 Uiso 1 1 calc R U . . .
N2 N 0.3007(5) 0.2857(4) 0.3704(3) 0.0413(13) Uani 1 1 d . . . . .
N3 N 0.3623(6) -0.0571(5) 0.3159(3) 0.0425(14) Uani 1 1 d . . . . .
N4 N 0.3087(6) -0.1396(4) 0.3214(3) 0.0432(14) Uani 1 1 d . . . . .
C1 C -0.1577(6) 0.4036(4) 0.5186(3) 0.0368(15) Uani 1 1 d . . . . .
C2 C -0.0464(6) 0.3435(5) 0.5306(4) 0.0398(16) Uani 1 1 d . . . . .
C3 C 0.0402(7) 0.3712(6) 0.5860(4) 0.0500(18) Uani 1 1 d . . . . .
H3 H 0.1177 0.3334 0.5957 0.060 Uiso 1 1 calc R U . . .
C4 C 0.0174(8) 0.4512(6) 0.6271(4) 0.0532(19) Uani 1 1 d . . . . .
H4 H 0.0800 0.4676 0.6633 0.064 Uiso 1 1 calc R U . . .
C5 C -0.0934(7) 0.5069(5) 0.6163(4) 0.0470(18) Uani 1 1 d . . . . .
H5 H -0.1107 0.5601 0.6460 0.056 Uiso 1 1 calc R U . . .
C6 C -0.1814(7) 0.4843(5) 0.5606(4) 0.0437(16) Uani 1 1 d . . . . .
H6 H -0.2575 0.5238 0.5513 0.052 Uiso 1 1 calc R U . . .
C7 C -0.0215(6) 0.2496(5) 0.4932(4) 0.0411(16) Uani 1 1 d . . . . .
C8 C 0.2613(6) 0.1906(5) 0.3750(3) 0.0361(14) Uani 1 1 d . . . . .
C9 C 0.1474(6) 0.1698(5) 0.4159(4) 0.0386(15) Uani 1 1 d . . . . .
C10 C 0.1027(8) 0.0748(5) 0.4218(4) 0.0486(18) Uani 1 1 d . . . . .
H10 H 0.0253 0.0610 0.4485 0.058 Uiso 1 1 calc R U . . .
C11 C 0.1715(7) -0.0002(5) 0.3885(4) 0.0461(17) Uani 1 1 d . . . . .
H11 H 0.1405 -0.0644 0.3937 0.055 Uiso 1 1 calc R U . . .
C12 C 0.2831(7) 0.0173(5) 0.3486(3) 0.0365(15) Uani 1 1 d . . . . .
C13 C 0.3327(7) 0.1150(5) 0.3411(4) 0.0395(15) Uani 1 1 d . . . . .
C14 C 0.4472(7) 0.1408(6) 0.3008(4) 0.0480(18) Uani 1 1 d . . . . .
H14 H 0.4981 0.0928 0.2777 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4823(7) 0.2357(6) 0.2960(4) 0.055(2) Uani 1 1 d . . . . .
H15 H 0.5576 0.2545 0.2692 0.066 Uiso 1 1 calc R U . . .
C16 C 0.4054(7) 0.3047(5) 0.3311(4) 0.0505(18) Uani 1 1 d . . . . .
H16 H 0.4308 0.3701 0.3261 0.061 Uiso 1 1 calc R U . . .
C17 C 0.3882(7) -0.2163(5) 0.2950(4) 0.0405(16) Uani 1 1 d . . . . .
C18 C 0.5091(7) -0.2045(5) 0.2571(4) 0.0443(16) Uani 1 1 d . . . . .
H18 H 0.5401 -0.1421 0.2455 0.053 Uiso 1 1 calc R U . . .
C19 C 0.5820(7) -0.2860(6) 0.2372(4) 0.0496(18) Uani 1 1 d . . . . .
H19 H 0.6633 -0.2790 0.2123 0.060 Uiso 1 1 calc R U . . .
C20 C 0.5350(7) -0.3767(5) 0.2541(4) 0.0469(17) Uani 1 1 d . . . . .
C21 C 0.4136(7) -0.3900(5) 0.2892(4) 0.0455(17) Uani 1 1 d . . . . .
H21 H 0.3821 -0.4527 0.2998 0.055 Uiso 1 1 calc R U . . .
C22 C 0.3400(7) -0.3089(5) 0.3081(4) 0.0429(16) Uani 1 1 d . . . . .
H22 H 0.2558 -0.3167 0.3302 0.051 Uiso 1 1 calc R U . . .
C23 C -0.3940(6) 0.3027(5) 0.4855(4) 0.0396(15) Uani 1 1 d . . . . .
C24 C -0.4922(6) 0.3413(6) 0.5294(4) 0.0479(18) Uani 1 1 d . . . . .
H24 H -0.4958 0.4087 0.5372 0.058 Uiso 1 1 calc R U . . .
C25 C -0.5822(7) 0.2824(7) 0.5607(4) 0.058(2) Uani 1 1 d . . . . .
H25 H -0.6466 0.3075 0.5921 0.069 Uiso 1 1 calc R U . . .
C26 C -0.5783(8) 0.1843(8) 0.5458(5) 0.066(3) Uani 1 1 d . . . . .
C27 C -0.4826(9) 0.1449(7) 0.5011(5) 0.068(2) Uani 1 1 d . . . . .
H27 H -0.4824 0.0779 0.4916 0.081 Uiso 1 1 calc R U . . .
C28 C -0.3889(8) 0.2039(5) 0.4712(4) 0.0544(19) Uani 1 1 d . . . . .
H28 H -0.3221 0.1784 0.4414 0.065 Uiso 1 1 calc R U . . .


_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 C20 1.894(7) . ?
Br2 C26 1.908(8) . ?
S1 O2 1.432(5) . ?
S1 O1 1.438(5) . ?
S1 C23 1.751(7) . ?
S1 C1 1.774(7) . ?
O3 C7 1.210(8) . ?
N1 C7 1.356(8) . ?
N1 C9 1.404(8) . ?
N2 C16 1.306(9) . ?
N2 C8 1.369(8) . ?
N3 N4 1.258(8) . ?
N3 C12 1.433(8) . ?
N4 C17 1.411(8) . ?
C1 C6 1.386(9) . ?
C1 C2 1.390(9) . ?
C2 C3 1.391(10) . ?
C2 C7 1.494(10) . ?
C3 C4 1.365(10) . ?
C4 C5 1.347(11) . ?
C5 C6 1.384(10) . ?
C8 C9 1.400(9) . ?
C8 C13 1.414(9) . ?
C9 C10 1.386(10) . ?
C10 C11 1.391(9) . ?
C11 C12 1.363(10) . ?
C12 C13 1.440(9) . ?
C13 C14 1.415(9) . ?
C14 C15 1.355(11) . ?
C15 C16 1.389(10) . ?
C17 C22 1.384(9) . ?
C17 C18 1.407(10) . ?
C18 C19 1.387(9) . ?
C19 C20 1.372(10) . ?
C20 C21 1.388(10) . ?
C21 C22 1.381(9) . ?
C23 C28 1.388(10) . ?
C23 C24 1.389(10) . ?
C24 C25 1.345(10) . ?
C25 C26 1.380(12) . ?
C26 C27 1.384(13) . ?
C27 C28 1.359(11) . ?

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 118.7(3) . . ?
O2 S1 C23 109.7(3) . . ?
O1 S1 C23 108.3(3) . . ?
O2 S1 C1 108.3(3) . . ?
O1 S1 C1 107.0(3) . . ?
C23 S1 C1 103.8(3) . . ?
C7 N1 C9 128.4(6) . . ?
C16 N2 C8 117.0(6) . . ?
N4 N3 C12 112.2(6) . . ?
N3 N4 C17 114.3(6) . . ?
C6 C1 C2 121.7(6) . . ?
C6 C1 S1 117.2(5) . . ?
C2 C1 S1 121.1(5) . . ?
C1 C2 C3 115.5(6) . . ?
C1 C2 C7 125.1(6) . . ?
C3 C2 C7 119.2(6) . . ?
C4 C3 C2 122.8(7) . . ?
C5 C4 C3 120.9(7) . . ?
C4 C5 C6 118.9(7) . . ?
C1 C6 C5 120.1(7) . . ?
O3 C7 N1 124.8(6) . . ?
O3 C7 C2 120.2(6) . . ?
N1 C7 C2 114.7(6) . . ?
N2 C8 C9 117.4(6) . . ?
N2 C8 C13 122.1(6) . . ?
C9 C8 C13 120.4(6) . . ?
C10 C9 C8 119.7(6) . . ?
C10 C9 N1 124.0(6) . . ?
C8 C9 N1 116.1(6) . . ?
C9 C10 C11 120.5(7) . . ?
C12 C11 C10 121.4(7) . . ?
C11 C12 N3 124.1(6) . . ?
C11 C12 C13 119.9(6) . . ?
N3 C12 C13 115.9(6) . . ?
C8 C13 C14 117.7(6) . . ?
C8 C13 C12 118.1(6) . . ?
C14 C13 C12 124.2(6) . . ?
C15 C14 C13 118.9(7) . . ?
C14 C15 C16 119.1(7) . . ?
N2 C16 C15 125.1(7) . . ?
C22 C17 C18 119.5(6) . . ?
C22 C17 N4 115.6(6) . . ?
C18 C17 N4 124.9(6) . . ?
C19 C18 C17 119.3(6) . . ?
C20 C19 C18 119.7(6) . . ?
C19 C20 C21 121.8(7) . . ?
C19 C20 Br1 119.4(5) . . ?
C21 C20 Br1 118.8(6) . . ?
C22 C21 C20 118.5(7) . . ?
C21 C22 C17 121.0(7) . . ?
C28 C23 C24 121.2(7) . . ?
C28 C23 S1 119.8(6) . . ?
C24 C23 S1 119.0(6) . . ?
C25 C24 C23 120.1(8) . . ?
C24 C25 C26 118.7(8) . . ?
C25 C26 C27 121.9(8) . . ?
C25 C26 Br2 119.0(7) . . ?
C27 C26 Br2 119.0(8) . . ?
C28 C27 C26 119.5(9) . . ?
C27 C28 C23 118.6(8) . . ?

_refine_diff_density_max         0.792
_refine_diff_density_min         -0.907
_refine_diff_density_rms         0.164

