# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_g200909b
_audit_block_doi                 10.5517/ccdc.csd.cc26hm7l
_database_code_depnum_ccdc_archive 'CCDC 2040799'
loop_
_audit_author_name
_audit_author_address
Yang
;Soochow University
China
;
_audit_update_record             
;
2020-10-27 deposited with the CCDC.	2021-10-07 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 H26 Br2 N2 O4 S'
_chemical_formula_weight         634.38

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'
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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.9489(3)
_cell_length_b                   10.2140(2)
_cell_length_c                   29.3155(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2679.54(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    5479
_cell_measurement_theta_min      4.3170
_cell_measurement_theta_max      76.9600

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    4.863
_shelx_estimated_absorpt_T_min   0.195
_shelx_estimated_absorpt_T_max   0.443
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.36975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11354
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         4.584
_diffrn_reflns_theta_max         77.614
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             5357
_reflns_number_gt                5016
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.659
_reflns_Friedel_fraction_max     0.865
_reflns_Friedel_fraction_full    0.903

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)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 1863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5357
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1540
_refine_ls_wR_factor_gt          0.1504
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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 0.33288(10) 0.94922(7) 0.23324(2) 0.0533(2) Uani 1 1 d . . . . .
Br2 Br 0.01090(11) 0.36577(7) 0.35859(3) 0.0624(3) Uani 1 1 d . . . . .
O1 O 0.8146(6) 1.0377(5) 0.4878(2) 0.0585(14) Uani 1 1 d . . . . .
O2 O 0.9174(6) 1.0340(6) 0.4095(3) 0.0650(16) Uani 1 1 d . . . . .
O3 O 0.3832(6) 1.2562(5) 0.28960(16) 0.0459(10) Uani 1 1 d . . . . .
O4 O 0.2989(5) 0.9691(4) 0.34791(13) 0.0351(8) Uani 1 1 d . . . . .
N1 N 0.6548(6) 1.1064(5) 0.42306(18) 0.0380(10) Uani 1 1 d . . . . .
N2 N 0.3694(6) 1.0857(5) 0.33683(17) 0.0354(10) Uani 1 1 d . . . . .
S1 S 0.79617(15) 1.01196(16) 0.44046(6) 0.0440(4) Uani 1 1 d . . . . .
C1 C 0.6167(7) 1.1178(6) 0.3754(2) 0.0402(12) Uani 1 1 d . . . . .
C2 C 0.4513(6) 1.1527(5) 0.37244(19) 0.0326(10) Uani 1 1 d . . . . .
H2 H 0.4445 1.2478 0.3662 0.039 Uiso 1 1 calc R U . . .
C3 C 0.3978(6) 1.1307(6) 0.42032(19) 0.0336(11) Uani 1 1 d . . . . .
C4 C 0.2519(7) 1.1360(7) 0.4369(2) 0.0412(12) Uani 1 1 d . . . . .
H4 H 0.1704 1.1481 0.4171 0.049 Uiso 1 1 calc R U . . .
C5 C 0.2311(8) 1.1229(8) 0.4835(3) 0.0487(15) Uani 1 1 d . . . . .
H5 H 0.1339 1.1230 0.4957 0.058 Uiso 1 1 calc R U . . .
C6 C 0.3532(9) 1.1098(7) 0.5122(2) 0.0478(15) Uani 1 1 d . . . . .
H6 H 0.3372 1.1039 0.5439 0.057 Uiso 1 1 calc R U . . .
C7 C 0.4993(8) 1.1050(7) 0.4956(2) 0.0441(13) Uani 1 1 d . . . . .
H7 H 0.5817 1.0970 0.5152 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5168(6) 1.1125(5) 0.4490(2) 0.0345(10) Uani 1 1 d . . . . .
C9 C 0.7045(9) 1.1073(11) 0.3395(3) 0.065(2) Uani 1 1 d . . . . .
H9A H 0.8069 1.0901 0.3434 0.078 Uiso 1 1 calc R U . . .
H9B H 0.6646 1.1170 0.3101 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7319(7) 0.8497(6) 0.4335(2) 0.0375(11) Uani 1 1 d . . . . .
C11 C 0.6362(9) 0.7975(7) 0.4657(2) 0.0462(15) Uani 1 1 d . . . . .
H11 H 0.6140 0.8444 0.4924 0.055 Uiso 1 1 calc R U . . .
C12 C 0.5736(10) 0.6759(7) 0.4582(2) 0.0509(16) Uani 1 1 d . . . . .
H12 H 0.5069 0.6406 0.4798 0.061 Uiso 1 1 calc R U . . .
C13 C 0.6087(8) 0.6048(6) 0.4190(2) 0.0399(12) Uani 1 1 d . . . . .
C14 C 0.7071(9) 0.6583(7) 0.3885(2) 0.0491(15) Uani 1 1 d . . . . .
H14 H 0.7332 0.6103 0.3623 0.059 Uiso 1 1 calc R U . . .
C15 C 0.7689(8) 0.7801(8) 0.3949(3) 0.0473(14) Uani 1 1 d . . . . .
H15 H 0.8354 0.8153 0.3733 0.057 Uiso 1 1 calc R U . . .
C16 C 0.5355(9) 0.4740(7) 0.4098(2) 0.0508(16) Uani 1 1 d . . . . .
H16A H 0.4990 0.4719 0.3787 0.076 Uiso 1 1 calc R U . . .
H16B H 0.4527 0.4617 0.4307 0.076 Uiso 1 1 calc R U . . .
H16C H 0.6080 0.4046 0.4142 0.076 Uiso 1 1 calc R U . . .
C17 C 0.3290(7) 1.1501(6) 0.29775(17) 0.0332(10) Uani 1 1 d . . . . .
C18 C 0.2147(7) 1.0875(6) 0.26483(19) 0.0361(11) Uani 1 1 d . . . . .
C19 C 0.0749(8) 1.0300(11) 0.2855(3) 0.059(2) Uani 1 1 d . . . . .
H19A H 0.0353 1.0898 0.3082 0.089 Uiso 1 1 calc R U . . .
H19B H 0.0986 0.9469 0.2998 0.089 Uiso 1 1 calc R U . . .
H19C H 0.0010 1.0164 0.2617 0.089 Uiso 1 1 calc R U . . .
C20 C 0.1739(10) 1.1900(8) 0.2289(2) 0.0542(16) Uani 1 1 d . . . . .
H20A H 0.1159 1.1490 0.2048 0.081 Uiso 1 1 calc R U . . .
H20B H 0.2645 1.2268 0.2161 0.081 Uiso 1 1 calc R U . . .
H20C H 0.1154 1.2590 0.2429 0.081 Uiso 1 1 calc R U . . .
C21 C 0.4038(7) 0.8617(6) 0.3507(2) 0.0406(12) Uani 1 1 d . . . . .
H21A H 0.4663 0.8697 0.3780 0.049 Uiso 1 1 calc R U . . .
H21B H 0.4686 0.8598 0.3238 0.049 Uiso 1 1 calc R U . . .
C22 C 0.3086(8) 0.7394(6) 0.3530(2) 0.0400(13) Uani 1 1 d . . . . .
C23 C 0.3179(9) 0.6467(7) 0.3186(2) 0.0460(14) Uani 1 1 d . . . . .
H23 H 0.3840 0.6601 0.2941 0.055 Uiso 1 1 calc R U . . .
C24 C 0.2308(8) 0.5344(6) 0.3199(2) 0.0448(14) Uani 1 1 d . . . . .
H24 H 0.2368 0.4711 0.2967 0.054 Uiso 1 1 calc R U . . .
C25 C 0.1351(7) 0.5187(5) 0.3563(2) 0.0432(13) Uani 1 1 d . . . . .
C26 C 0.1242(9) 0.6092(7) 0.3909(2) 0.0486(15) Uani 1 1 d . . . . .
H26 H 0.0582 0.5959 0.4154 0.058 Uiso 1 1 calc R U . . .
C27 C 0.2121(9) 0.7199(7) 0.3888(2) 0.0484(15) Uani 1 1 d . . . . .
H27 H 0.2059 0.7827 0.4122 0.058 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 C18 1.993(6) . ?
Br2 C25 1.918(6) . ?
O1 S1 1.423(6) . ?
O2 S1 1.432(6) . ?
O3 C17 1.211(8) . ?
O4 N2 1.386(6) . ?
O4 C21 1.447(8) . ?
N1 C1 1.442(8) . ?
N1 C8 1.452(8) . ?
N1 S1 1.670(5) . ?
N2 C17 1.370(7) . ?
N2 C2 1.448(7) . ?
S1 C10 1.767(6) . ?
C1 C9 1.317(11) . ?
C1 C2 1.525(8) . ?
C2 C3 1.500(8) . ?
C2 H2 0.9900 . ?
C3 C8 1.369(8) . ?
C3 C4 1.394(8) . ?
C4 C5 1.386(10) . ?
C4 H4 0.9400 . ?
C5 C6 1.386(11) . ?
C5 H5 0.9400 . ?
C6 C7 1.397(11) . ?
C6 H6 0.9400 . ?
C7 C8 1.377(9) . ?
C7 H7 0.9400 . ?
C9 H9A 0.9400 . ?
C9 H9B 0.9400 . ?
C10 C15 1.375(9) . ?
C10 C11 1.382(10) . ?
C11 C12 1.380(11) . ?
C11 H11 0.9400 . ?
C12 C13 1.397(9) . ?
C12 H12 0.9400 . ?
C13 C14 1.370(11) . ?
C13 C16 1.511(9) . ?
C14 C15 1.374(11) . ?
C14 H14 0.9400 . ?
C15 H15 0.9400 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?
C17 C18 1.545(8) . ?
C18 C19 1.508(10) . ?
C18 C20 1.529(9) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C21 C22 1.513(8) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C27 1.374(10) . ?
C22 C23 1.385(9) . ?
C23 C24 1.388(10) . ?
C23 H23 0.9400 . ?
C24 C25 1.379(11) . ?
C24 H24 0.9400 . ?
C25 C26 1.374(10) . ?
C26 C27 1.378(10) . ?
C26 H26 0.9400 . ?
C27 H27 0.9400 . ?

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
N2 O4 C21 111.7(4) . . ?
C1 N1 C8 107.6(5) . . ?
C1 N1 S1 121.4(5) . . ?
C8 N1 S1 120.7(4) . . ?
C17 N2 O4 119.2(5) . . ?
C17 N2 C2 120.6(5) . . ?
O4 N2 C2 117.9(4) . . ?
O1 S1 O2 120.2(4) . . ?
O1 S1 N1 106.2(3) . . ?
O2 S1 N1 106.8(3) . . ?
O1 S1 C10 108.9(3) . . ?
O2 S1 C10 108.7(3) . . ?
N1 S1 C10 105.1(3) . . ?
C9 C1 N1 128.8(7) . . ?
C9 C1 C2 123.5(7) . . ?
N1 C1 C2 107.7(5) . . ?
N2 C2 C3 116.2(5) . . ?
N2 C2 C1 115.0(5) . . ?
C3 C2 C1 102.8(5) . . ?
N2 C2 H2 107.5 . . ?
C3 C2 H2 107.5 . . ?
C1 C2 H2 107.5 . . ?
C8 C3 C4 121.3(6) . . ?
C8 C3 C2 110.2(5) . . ?
C4 C3 C2 128.3(5) . . ?
C5 C4 C3 117.8(6) . . ?
C5 C4 H4 121.1 . . ?
C3 C4 H4 121.1 . . ?
C4 C5 C6 120.2(6) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 121.9(6) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 116.9(6) . . ?
C8 C7 H7 121.6 . . ?
C6 C7 H7 121.6 . . ?
C3 C8 C7 121.8(6) . . ?
C3 C8 N1 110.3(5) . . ?
C7 C8 N1 127.8(6) . . ?
C1 C9 H9A 120.0 . . ?
C1 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C15 C10 C11 120.8(6) . . ?
C15 C10 S1 120.1(5) . . ?
C11 C10 S1 119.0(5) . . ?
C12 C11 C10 119.4(6) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.5(7) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 118.4(6) . . ?
C14 C13 C16 121.0(6) . . ?
C12 C13 C16 120.6(7) . . ?
C13 C14 C15 122.0(6) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 H14 119.0 . . ?
C14 C15 C10 118.9(6) . . ?
C14 C15 H15 120.5 . . ?
C10 C15 H15 120.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 N2 119.3(5) . . ?
O3 C17 C18 120.8(5) . . ?
N2 C17 C18 119.9(5) . . ?
C19 C18 C20 110.2(6) . . ?
C19 C18 C17 117.4(5) . . ?
C20 C18 C17 107.8(5) . . ?
C19 C18 Br1 110.5(5) . . ?
C20 C18 Br1 106.9(4) . . ?
C17 C18 Br1 103.4(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 C21 C22 105.3(5) . . ?
O4 C21 H21A 110.7 . . ?
C22 C21 H21A 110.7 . . ?
O4 C21 H21B 110.7 . . ?
C22 C21 H21B 110.7 . . ?
H21A C21 H21B 108.8 . . ?
C27 C22 C23 119.7(6) . . ?
C27 C22 C21 120.5(6) . . ?
C23 C22 C21 119.8(6) . . ?
C22 C23 C24 120.8(7) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C25 C24 C23 117.7(6) . . ?
C25 C24 H24 121.1 . . ?
C23 C24 H24 121.1 . . ?
C26 C25 C24 122.5(6) . . ?
C26 C25 Br2 118.7(5) . . ?
C24 C25 Br2 118.8(5) . . ?
C25 C26 C27 118.6(7) . . ?
C25 C26 H26 120.7 . . ?
C27 C26 H26 120.7 . . ?
C22 C27 C26 120.7(6) . . ?
C22 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?

_refine_diff_density_max         0.982
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.132

