# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_8k
_database_code_depnum_ccdc_archive 'CCDC 1910836'
loop_
_audit_author_name
_audit_author_address
'Regis Guillot'
;ICMMO UMR CNRS Universite Paris Sud Universite Paris Saclay FRANCE
France
;
_audit_update_record             
;
2019-04-17 deposited with the CCDC.	2020-01-07 downloaded from the CCDC.
;

#cu_v746_GuillotICMMO

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C26 H25 Br N2 O6 S2 '
_chemical_formula_sum            'C26 H25 Br N2 O6 S2'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         605.51

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 0.0096 '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 0.0189 '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'
S S 0.3331 0.5567 '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'

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

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

_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.
;

_cell_length_a                   8.6142(9)
_cell_length_b                   15.2562(15)
_cell_length_c                   10.0113(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.761(4)
_cell_angle_gamma                90
_cell_volume                     1312.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      5.15
_cell_measurement_theta_max      66.72
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.025
_exptl_absorpt_coefficient_mu    4.001
_shelx_estimated_absorpt_T_min   0.631
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_T_max  0.8816
_exptl_absorpt_process_details   'apex3 Bruker'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14066
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.426
_diffrn_reflns_theta_max         66.959
_diffrn_reflns_theta_full        66.959
_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 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4552
_reflns_number_gt                4467
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.897
_reflns_Friedel_fraction_max     0.961
_reflns_Friedel_fraction_full    0.961

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0321P)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 2068 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(6)
_refine_ls_number_reflns         4552
_refine_ls_number_parameters     337
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0562
_refine_ls_wR_factor_gt          0.0559
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_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
C1 C 0.9736(5) 0.1647(2) 1.1070(4) 0.0333(8) Uani 1 1 d . . . . .
H1A H 0.886603 0.128608 1.133389 0.050 Uiso 1 1 calc R U . . .
H1B H 1.020235 0.195481 1.185693 0.050 Uiso 1 1 calc R U . . .
H1C H 1.051928 0.127186 1.069240 0.050 Uiso 1 1 calc R U . . .
C2 C 0.9148(3) 0.2310(3) 1.0032(3) 0.0220(6) Uani 1 1 d . . . . .
C3 C 0.9107(4) 0.3201(2) 1.0332(3) 0.0223(7) Uani 1 1 d . . . . .
H3 H 0.942469 0.339568 1.120882 0.027 Uiso 1 1 calc R U . . .
C4 C 0.8608(4) 0.3808(2) 0.9366(3) 0.0196(6) Uani 1 1 d . . . . .
H4 H 0.858303 0.441434 0.957848 0.023 Uiso 1 1 calc R U . . .
C5 C 0.8144(3) 0.3521(2) 0.8083(3) 0.0154(6) Uani 1 1 d . . . . .
C6 C 0.8149(4) 0.2635(2) 0.7763(3) 0.0197(7) Uani 1 1 d . . . . .
H6 H 0.781940 0.244312 0.688760 0.024 Uiso 1 1 calc R U . . .
C7 C 0.8642(4) 0.2038(2) 0.8738(4) 0.0229(7) Uani 1 1 d . . . . .
H7 H 0.863839 0.143064 0.852708 0.028 Uiso 1 1 calc R U . . .
C8 C 0.4901(6) 0.8334(3) 0.8193(4) 0.0400(10) Uani 1 1 d . . . . .
H8A H 0.409614 0.877770 0.799318 0.060 Uiso 1 1 calc R U . . .
H8B H 0.593078 0.860409 0.815982 0.060 Uiso 1 1 calc R U . . .
H8C H 0.478751 0.809323 0.908811 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4732(5) 0.7608(2) 0.7172(4) 0.0279(8) Uani 1 1 d . . . . .
C10 C 0.3263(4) 0.7346(3) 0.6637(3) 0.0261(6) Uani 1 1 d . . . . .
H10 H 0.236135 0.764042 0.690115 0.031 Uiso 1 1 calc R U . . .
C11 C 0.3106(4) 0.6660(2) 0.5725(3) 0.0215(7) Uani 1 1 d . . . . .
H11 H 0.210893 0.649197 0.534985 0.026 Uiso 1 1 calc R U . . .
C12 C 0.4431(4) 0.62253(19) 0.5373(3) 0.0178(6) Uani 1 1 d . . . . .
C13 C 0.5904(4) 0.6492(2) 0.5859(3) 0.0223(7) Uani 1 1 d . . . . .
H13 H 0.680555 0.620465 0.557948 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6037(4) 0.7183(2) 0.6756(4) 0.0270(8) Uani 1 1 d . . . . .
H14 H 0.704082 0.736775 0.709211 0.032 Uiso 1 1 calc R U . . .
C15 C 0.5013(4) 0.4703(2) 0.7958(3) 0.0154(6) Uani 1 1 d . . . . .
C16 C 0.5467(4) 0.5341(2) 0.8896(3) 0.0220(6) Uani 1 1 d . . . . .
H16 H 0.637516 0.568456 0.881258 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4525(4) 0.5452(2) 0.9966(3) 0.0269(8) Uani 1 1 d . . . . .
H17 H 0.480445 0.587578 1.063468 0.032 Uiso 1 1 calc R U . . .
C18 C 0.3184(4) 0.4955(2) 1.0072(3) 0.0272(8) Uani 1 1 d . . . . .
H18 H 0.256597 0.504364 1.081244 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2737(4) 0.4334(2) 0.9116(3) 0.0215(7) Uani 1 1 d . . . . .
H19 H 0.181223 0.400200 0.918285 0.026 Uiso 1 1 calc R U . . .
C20 C 0.3673(3) 0.42069(19) 0.8058(3) 0.0145(6) Uani 1 1 d . . . . .
C21 C 0.3463(3) 0.35849(19) 0.6909(3) 0.0140(6) Uani 1 1 d . . . . .
C22 C 0.1890(3) 0.3592(2) 0.6125(3) 0.0171(6) Uani 1 1 d . . . . .
H22A H 0.102654 0.359113 0.672977 0.021 Uiso 1 1 calc R U . . .
H22B H 0.177545 0.308370 0.551187 0.021 Uiso 1 1 calc R U . . .
C23 C 0.1949(3) 0.4453(2) 0.5349(3) 0.0157(6) Uani 1 1 d . . . . .
H23 H 0.168252 0.496029 0.592283 0.019 Uiso 1 1 calc R U . . .
C24 C 0.4639(3) 0.39410(19) 0.5938(3) 0.0137(6) Uani 1 1 d . . . . .
H24 H 0.515790 0.346218 0.545096 0.016 Uiso 1 1 calc R U . . .
C25 C 0.0872(3) 0.4420(2) 0.4064(3) 0.0175(6) Uani 1 1 d . . . . .
C26 C -0.1053(4) 0.5163(3) 0.2766(4) 0.0257(7) Uani 1 1 d . . . . .
H26A H -0.176907 0.466322 0.274358 0.039 Uiso 1 1 calc R U . . .
H26B H -0.042926 0.514220 0.198302 0.039 Uiso 1 1 calc R U . . .
H26C H -0.165064 0.571007 0.275474 0.039 Uiso 1 1 calc R U . . .
N1 N 0.5756(3) 0.44727(16) 0.6774(2) 0.0150(5) Uani 1 1 d . . . . .
N2 N 0.3597(3) 0.44865(16) 0.5031(2) 0.0148(5) Uani 1 1 d . . . . .
O1 O 0.7936(3) 0.38986(15) 0.5550(2) 0.0204(5) Uani 1 1 d . . . . .
O2 O 0.8382(3) 0.51000(14) 0.7214(2) 0.0225(5) Uani 1 1 d . . . . .
O3 O 0.5757(3) 0.51129(15) 0.3846(2) 0.0225(5) Uani 1 1 d . . . . .
O4 O 0.3027(3) 0.55583(15) 0.3244(2) 0.0207(5) Uani 1 1 d . . . . .
O5 O 0.0866(3) 0.38330(16) 0.3274(2) 0.0252(5) Uani 1 1 d . . . . .
O6 O -0.0041(3) 0.51247(14) 0.3968(2) 0.0193(5) Uani 1 1 d . . . . .
S1 S 0.76564(8) 0.42897(5) 0.68070(7) 0.01548(16) Uani 1 1 d . . . . .
S2 S 0.42478(8) 0.53416(5) 0.42342(7) 0.01568(16) Uani 1 1 d . . . . .
Br Br 0.39918(3) 0.23874(2) 0.75354(3) 0.01948(9) 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
C1 C2 1.513(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.393(5) . ?
C2 C7 1.402(5) . ?
C3 C4 1.386(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(5) . ?
C5 S1 1.764(3) . ?
C6 C7 1.382(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.508(5) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.386(6) . ?
C9 C10 1.400(5) . ?
C10 C11 1.390(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.389(5) . ?
C12 S2 1.766(3) . ?
C13 C14 1.384(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C20 1.389(4) . ?
C15 C16 1.391(5) . ?
C15 N1 1.428(4) . ?
C16 C17 1.396(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.386(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.493(4) . ?
C21 C22 1.521(4) . ?
C21 C24 1.548(4) . ?
C21 Br 1.975(3) . ?
C22 C23 1.527(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N2 1.476(4) . ?
C23 C25 1.537(4) . ?
C23 H23 1.0000 . ?
C24 N1 1.476(4) . ?
C24 N2 1.489(4) . ?
C24 H24 1.0000 . ?
C25 O5 1.195(4) . ?
C25 O6 1.332(4) . ?
C26 O6 1.440(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 S1 1.659(2) . ?
N2 S2 1.646(3) . ?
O1 S1 1.427(2) . ?
O2 S1 1.432(2) . ?
O3 S2 1.424(2) . ?
O4 S2 1.436(2) . ?

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 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.5(3) . . ?
C3 C2 C1 121.1(3) . . ?
C7 C2 C1 120.4(4) . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 S1 119.0(3) . . ?
C4 C5 S1 120.0(2) . . ?
C7 C6 C5 119.0(3) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.3(3) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 118.8(3) . . ?
C14 C9 C8 120.3(4) . . ?
C10 C9 C8 121.0(4) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11 120.6 . . ?
C10 C11 H11 120.6 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 S2 119.3(2) . . ?
C13 C12 S2 119.4(3) . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
C20 C15 C16 122.1(3) . . ?
C20 C15 N1 110.2(3) . . ?
C16 C15 N1 127.7(3) . . ?
C15 C16 C17 116.8(3) . . ?
C15 C16 H16 121.6 . . ?
C17 C16 H16 121.6 . . ?
C18 C17 C16 121.3(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 121.0(3) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 118.4(3) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C15 120.5(3) . . ?
C19 C20 C21 129.1(3) . . ?
C15 C20 C21 110.5(3) . . ?
C20 C21 C22 116.9(2) . . ?
C20 C21 C24 102.1(2) . . ?
C22 C21 C24 105.7(2) . . ?
C20 C21 Br 109.23(19) . . ?
C22 C21 Br 110.5(2) . . ?
C24 C21 Br 112.16(19) . . ?
C21 C22 C23 102.2(2) . . ?
C21 C22 H22A 111.3 . . ?
C23 C22 H22A 111.3 . . ?
C21 C22 H22B 111.3 . . ?
C23 C22 H22B 111.3 . . ?
H22A C22 H22B 109.2 . . ?
N2 C23 C22 101.8(2) . . ?
N2 C23 C25 110.9(2) . . ?
C22 C23 C25 111.1(2) . . ?
N2 C23 H23 110.9 . . ?
C22 C23 H23 110.9 . . ?
C25 C23 H23 110.9 . . ?
N1 C24 N2 112.5(2) . . ?
N1 C24 C21 105.4(2) . . ?
N2 C24 C21 100.7(2) . . ?
N1 C24 H24 112.5 . . ?
N2 C24 H24 112.5 . . ?
C21 C24 H24 112.5 . . ?
O5 C25 O6 125.4(3) . . ?
O5 C25 C23 123.7(3) . . ?
O6 C25 C23 110.9(2) . . ?
O6 C26 H26A 109.5 . . ?
O6 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O6 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C15 N1 C24 107.2(2) . . ?
C15 N1 S1 121.4(2) . . ?
C24 N1 S1 121.7(2) . . ?
C23 N2 C24 113.5(2) . . ?
C23 N2 S2 119.7(2) . . ?
C24 N2 S2 121.8(2) . . ?
C25 O6 C26 114.6(3) . . ?
O1 S1 O2 121.07(14) . . ?
O1 S1 N1 106.01(13) . . ?
O2 S1 N1 105.79(13) . . ?
O1 S1 C5 108.32(14) . . ?
O2 S1 C5 106.82(14) . . ?
N1 S1 C5 108.30(13) . . ?
O3 S2 O4 120.56(14) . . ?
O3 S2 N2 106.50(13) . . ?
O4 S2 N2 105.04(13) . . ?
O3 S2 C12 108.56(15) . . ?
O4 S2 C12 107.48(14) . . ?
N2 S2 C12 108.14(14) . . ?

_refine_diff_density_max         0.398
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.054

