# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_20190909LI_ZNZ5256_28_3_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc244t8d
_database_code_depnum_ccdc_archive 'CCDC 1970833'
loop_
_audit_author_name
_audit_author_address
'Chunhao Yuan'
;Shandong First Medical University  Shandong Academy of Medical Sciences 
China
;
_audit_update_record             
;
2019-12-06 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 N2 O6 S'
_chemical_formula_weight         506.56

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.8523(4)
_cell_length_b                   10.2310(5)
_cell_length_c                   14.4737(6)
_cell_angle_alpha                79.614(2)
_cell_angle_beta                 82.176(2)
_cell_angle_gamma                76.804(2)
_cell_volume                     1249.14(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5462
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      28.18

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.175
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.981
_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      193(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            12452
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         28.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             6095
_reflns_number_gt                4924
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0417P)²+0.3959P] 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         6095
_refine_ls_number_parameters     326
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.4662(2) 1.09390(17) 0.83261(12) 0.0419(4) Uani 1 1 d . . . . .
H1 H 0.539738 1.127750 0.785690 0.050 Uiso 1 1 calc R U . . .
C2 C 0.3381(2) 1.18178(19) 0.86917(14) 0.0508(4) Uani 1 1 d . . . . .
H2 H 0.323367 1.276768 0.847667 0.061 Uiso 1 1 calc R U . . .
C3 C 0.2323(2) 1.1312(2) 0.93668(14) 0.0562(5) Uani 1 1 d . . . . .
H3 H 0.144036 1.191731 0.961208 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2526(2) 0.9937(2) 0.96924(13) 0.0551(5) Uani 1 1 d . . . . .
H4 H 0.178622 0.960212 1.016003 0.066 Uiso 1 1 calc R U . . .
C5 C 0.3809(2) 0.90410(18) 0.93385(11) 0.0445(4) Uani 1 1 d . . . . .
H5 H 0.396120 0.809320 0.956263 0.053 Uiso 1 1 calc R U . . .
C6 C 0.48561(18) 0.95549(16) 0.86556(11) 0.0354(3) Uani 1 1 d . . . . .
C7 C 0.54392(17) 0.67618(15) 0.72883(10) 0.0320(3) Uani 1 1 d . . . . .
C8 C 0.40086(18) 0.65805(16) 0.79142(11) 0.0351(3) Uani 1 1 d . . . . .
C9 C 0.26344(19) 0.75550(19) 0.77983(12) 0.0453(4) Uani 1 1 d . . . . .
H9 H 0.261454 0.831444 0.731014 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1298(2) 0.7417(2) 0.83947(15) 0.0579(5) Uani 1 1 d . . . . .
H10 H 0.035656 0.807060 0.830425 0.069 Uiso 1 1 calc R U . . .
C11 C 0.1327(2) 0.6339(2) 0.91154(15) 0.0591(5) Uani 1 1 d . . . . .
H11 H 0.040649 0.625056 0.952193 0.071 Uiso 1 1 calc R U . . .
C12 C 0.2687(2) 0.5386(2) 0.92513(13) 0.0548(5) Uani 1 1 d . . . . .
H12 H 0.271157 0.465302 0.975992 0.066 Uiso 1 1 calc R U . . .
C13 C 0.4019(2) 0.54985(18) 0.86446(11) 0.0441(4) Uani 1 1 d . . . . .
H13 H 0.494879 0.482763 0.873003 0.053 Uiso 1 1 calc R U . . .
C14 C 0.63399(16) 0.59292(15) 0.67162(10) 0.0314(3) Uani 1 1 d . . . . .
C15 C 0.59002(18) 0.46872(16) 0.65177(10) 0.0351(3) Uani 1 1 d . . . . .
C16 C 0.6577(2) 0.30300(18) 0.54868(13) 0.0484(4) Uani 1 1 d . . . . .
H16A H 0.548993 0.311229 0.535144 0.058 Uiso 1 1 calc R U . . .
H16B H 0.682664 0.226091 0.600327 0.058 Uiso 1 1 calc R U . . .
C17 C 0.7674(2) 0.2805(2) 0.46265(14) 0.0529(5) Uani 1 1 d . . . . .
H17A H 0.736801 0.354114 0.410894 0.079 Uiso 1 1 calc R U . . .
H17B H 0.764113 0.193421 0.444642 0.079 Uiso 1 1 calc R U . . .
H17C H 0.873492 0.279202 0.475818 0.079 Uiso 1 1 calc R U . . .
C18 C 0.78270(17) 0.62991(15) 0.62150(10) 0.0342(3) Uani 1 1 d . . . . .
H18A H 0.839424 0.656385 0.667195 0.041 Uiso 1 1 calc R U . . .
H18B H 0.849747 0.549109 0.597466 0.041 Uiso 1 1 calc R U . . .
C19 C 0.6884(2) 0.87245(17) 0.55022(11) 0.0414(4) Uani 1 1 d . . . . .
C20 C 0.5760(2) 0.90137(17) 0.63684(12) 0.0464(4) Uani 1 1 d . . . . .
H20A H 0.585720 0.989600 0.651796 0.056 Uiso 1 1 calc R U . . .
H20B H 0.468925 0.913356 0.619179 0.056 Uiso 1 1 calc R U . . .
C21 C 0.7948(2) 0.7074(2) 0.38568(12) 0.0465(4) Uani 1 1 d . . . . .
H21A H 0.708288 0.785890 0.370764 0.056 Uiso 1 1 calc R U . . .
H21B H 0.752949 0.623367 0.399452 0.056 Uiso 1 1 calc R U . . .
C22 C 0.92028(17) 0.69972(17) 0.30490(11) 0.0371(3) Uani 1 1 d . . . . .
C23 C 0.9519(2) 0.59333(17) 0.25375(12) 0.0420(4) Uani 1 1 d . . . . .
H23 H 0.892997 0.524167 0.269313 0.050 Uiso 1 1 calc R U . . .
C24 C 1.0691(2) 0.58704(19) 0.17988(13) 0.0487(4) Uani 1 1 d . . . . .
H24 H 1.090655 0.513442 0.145063 0.058 Uiso 1 1 calc R U . . .
C25 C 1.1544(2) 0.6870(2) 0.15680(13) 0.0533(5) Uani 1 1 d . . . . .
H25 H 1.235366 0.682068 0.106434 0.064 Uiso 1 1 calc R U . . .
C26 C 1.1223(2) 0.7944(2) 0.20683(13) 0.0554(5) Uani 1 1 d . . . . .
H26 H 1.180555 0.863946 0.190454 0.066 Uiso 1 1 calc R U . . .
C27 C 1.0057(2) 0.8011(2) 0.28060(12) 0.0481(4) Uani 1 1 d . . . . .
H27 H 0.983883 0.875366 0.314847 0.058 Uiso 1 1 calc R U . . .
N1 N 0.75492(16) 0.74156(14) 0.54256(9) 0.0400(3) Uani 1 1 d . . . . .
N2 N 0.59052(16) 0.80273(13) 0.72370(9) 0.0371(3) Uani 1 1 d . . . . .
O1 O 0.67822(15) 0.72033(12) 0.88074(9) 0.0500(3) Uani 1 1 d . . . . .
O2 O 0.76358(14) 0.91976(14) 0.78119(11) 0.0584(4) Uani 1 1 d . . . . .
O3 O 0.70282(17) 0.96691(14) 0.48752(9) 0.0568(3) Uani 1 1 d . . . . .
O4 O 0.86767(13) 0.72315(13) 0.46512(7) 0.0442(3) Uani 1 1 d . . . . .
O5 O 0.67664(14) 0.42803(12) 0.57528(8) 0.0459(3) Uani 1 1 d . . . . .
O6 O 0.49125(16) 0.41333(14) 0.69500(9) 0.0570(4) Uani 1 1 d . . . . .
S1 S 0.64530(4) 0.84403(4) 0.81655(3) 0.03848(11) 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 1.385(2) . ?
C1 C6 1.389(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(2) . ?
C5 H5 0.9500 . ?
C6 S1 1.7562(15) . ?
C7 C14 1.346(2) . ?
C7 N2 1.4327(19) . ?
C7 C8 1.481(2) . ?
C8 C13 1.385(2) . ?
C8 C9 1.394(2) . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.372(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.496(2) . ?
C14 C18 1.507(2) . ?
C15 O6 1.1943(19) . ?
C15 O5 1.3328(18) . ?
C16 O5 1.4510(18) . ?
C16 C17 1.489(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 N1 1.4657(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O3 1.2175(19) . ?
C19 N1 1.352(2) . ?
C19 C20 1.520(2) . ?
C20 N2 1.464(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 O4 1.4422(19) . ?
C21 C22 1.499(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.381(2) . ?
C22 C27 1.388(2) . ?
C23 C24 1.384(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.374(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.379(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(3) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
N1 O4 1.4049(16) . ?
N2 S1 1.6419(13) . ?
O1 S1 1.4251(13) . ?
O2 S1 1.4283(13) . ?

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 119.00(17) . . ?
C2 C1 H1 120.5 . . ?
C6 C1 H1 120.5 . . ?
C3 C2 C1 119.83(18) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.82(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 120.18(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 118.63(17) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 121.53(15) . . ?
C5 C6 S1 119.64(13) . . ?
C1 C6 S1 118.81(13) . . ?
C14 C7 N2 114.30(13) . . ?
C14 C7 C8 129.20(14) . . ?
N2 C7 C8 116.42(13) . . ?
C13 C8 C9 118.95(15) . . ?
C13 C8 C7 121.54(14) . . ?
C9 C8 C7 119.43(15) . . ?
C10 C9 C8 120.05(18) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C11 C10 C9 120.31(18) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 120.22(18) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C13 119.85(19) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.59(17) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
C7 C14 C15 123.16(13) . . ?
C7 C14 C18 118.53(13) . . ?
C15 C14 C18 118.25(12) . . ?
O6 C15 O5 123.56(14) . . ?
O6 C15 C14 126.87(14) . . ?
O5 C15 C14 109.55(12) . . ?
O5 C16 C17 106.58(14) . . ?
O5 C16 H16A 110.4 . . ?
C17 C16 H16A 110.4 . . ?
O5 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N1 C18 C14 112.68(12) . . ?
N1 C18 H18A 109.1 . . ?
C14 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C14 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
O3 C19 N1 123.25(17) . . ?
O3 C19 C20 118.22(16) . . ?
N1 C19 C20 118.18(14) . . ?
N2 C20 C19 118.98(14) . . ?
N2 C20 H20A 107.6 . . ?
C19 C20 H20A 107.6 . . ?
N2 C20 H20B 107.6 . . ?
C19 C20 H20B 107.6 . . ?
H20A C20 H20B 107.0 . . ?
O4 C21 C22 105.87(12) . . ?
O4 C21 H21A 110.6 . . ?
C22 C21 H21A 110.6 . . ?
O4 C21 H21B 110.6 . . ?
C22 C21 H21B 110.6 . . ?
H21A C21 H21B 108.7 . . ?
C23 C22 C27 119.30(15) . . ?
C23 C22 C21 120.96(15) . . ?
C27 C22 C21 119.74(16) . . ?
C22 C23 C24 120.27(16) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 120.16(17) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C24 C25 C26 119.92(17) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C27 120.19(17) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C26 C27 C22 120.16(17) . . ?
C26 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
C19 N1 O4 115.01(13) . . ?
C19 N1 C18 125.62(13) . . ?
O4 N1 C18 112.29(12) . . ?
C7 N2 C20 119.34(12) . . ?
C7 N2 S1 120.93(10) . . ?
C20 N2 S1 119.51(11) . . ?
N1 O4 C21 109.63(11) . . ?
C15 O5 C16 117.45(12) . . ?
O1 S1 O2 120.83(8) . . ?
O1 S1 N2 105.41(7) . . ?
O2 S1 N2 105.85(8) . . ?
O1 S1 C6 109.45(8) . . ?
O2 S1 C6 107.25(8) . . ?
N2 S1 C6 107.31(7) . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_20191229LI_ZNZ2846_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2499zr
_database_code_depnum_ccdc_archive 'CCDC 1975164'
loop_
_audit_author_name
_audit_author_address
'Chunhao Yuan'
;Shandong First Medical University  Shandong Academy of Medical Sciences 
China
;
_audit_update_record             
;
2020-01-02 deposited with the CCDC.	2020-01-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H29 Br N2 O6 S'
_chemical_formula_weight         601.50

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   10.1845(6)
_cell_length_b                   12.6592(8)
_cell_length_c                   12.8148(8)
_cell_angle_alpha                62.147(2)
_cell_angle_beta                 77.425(2)
_cell_angle_gamma                70.019(2)
_cell_volume                     1369.49(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9860
_cell_measurement_theta_min      3.58
_cell_measurement_theta_max      53.93

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             620
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    2.064
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.852
_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      193(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\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            18103
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.402
_diffrn_reflns_theta_max         54.027
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4998
_reflns_number_gt                4651
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.0332P)²+2.1052P] 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         4998
_refine_ls_number_parameters     347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_restrained_S_all      1.160
_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
C1 C 0.6220(3) 0.0077(3) 0.6398(3) 0.0327(7) Uani 1 1 d . . . . .
H1A H 0.557811 0.005006 0.706428 0.039 Uiso 1 1 calc R U . . .
C2 C 0.7583(4) -0.0670(3) 0.6567(3) 0.0367(7) Uani 1 1 d . . . . .
H2 H 0.787506 -0.120446 0.734531 0.044 Uiso 1 1 calc R U . . .
C3 C 0.8522(3) -0.0639(3) 0.5599(3) 0.0367(7) Uani 1 1 d . . . . .
H3 H 0.945621 -0.115883 0.571105 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8093(4) 0.0152(3) 0.4468(3) 0.0369(8) Uani 1 1 d . . . . .
H4 H 0.873634 0.017773 0.380255 0.044 Uiso 1 1 calc R U . . .
C5 C 0.6731(3) 0.0906(3) 0.4303(3) 0.0325(7) Uani 1 1 d . . . . .
H5 H 0.644591 0.145262 0.352372 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5780(3) 0.0869(3) 0.5264(3) 0.0273(6) Uani 1 1 d . . . . .
C7 C 0.4272(3) 0.1607(3) 0.5106(3) 0.0296(7) Uani 1 1 d . . . . .
H7A H 0.392487 0.155952 0.446932 0.036 Uiso 1 1 calc R U . . .
H7B H 0.369578 0.126755 0.584715 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2448(3) 0.4578(3) 0.3560(3) 0.0247(6) Uani 1 1 d . . . . .
C9 C 0.3654(3) 0.4776(3) 0.2617(3) 0.0300(7) Uani 1 1 d . . . . .
H9 H 0.450467 0.463283 0.298681 0.036 Uiso 1 1 calc R U . A 1
C10 C 0.1825(3) 0.3396(3) 0.5696(2) 0.0245(6) Uani 1 1 d . . . . .
H10A H 0.156615 0.261801 0.596316 0.029 Uiso 1 1 calc R U . . .
H10B H 0.095683 0.409347 0.552958 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2539(3) 0.3312(3) 0.6656(3) 0.0249(6) Uani 1 1 d . . . . .
C12 C 0.3146(3) 0.4350(3) 0.6329(3) 0.0279(6) Uani 1 1 d . . . . .
C13 C 0.2853(4) 0.6513(3) 0.5140(3) 0.0378(8) Uani 1 1 d . . . . .
H13A H 0.383368 0.639599 0.479784 0.045 Uiso 1 1 calc R U . . .
H13B H 0.278215 0.671222 0.581430 0.045 Uiso 1 1 calc R U . . .
C14 C 0.1879(5) 0.7526(3) 0.4226(4) 0.0563(11) Uani 1 1 d . . . . .
H14A H 0.203479 0.735707 0.353045 0.084 Uiso 1 1 calc R U . . .
H14B H 0.205384 0.832403 0.399690 0.084 Uiso 1 1 calc R U . . .
H14C H 0.090852 0.756302 0.455297 0.084 Uiso 1 1 calc R U . . .
C15 C 0.2689(3) 0.2345(3) 0.7741(3) 0.0255(6) Uani 1 1 d . . . . .
C16 C 0.2062(3) 0.1302(3) 0.8168(2) 0.0260(6) Uani 1 1 d . . . . .
C17 C 0.2919(3) 0.0084(3) 0.8682(3) 0.0322(7) Uani 1 1 d . . . . .
H17 H 0.386665 -0.006306 0.879989 0.039 Uiso 1 1 calc R U . . .
C18 C 0.2387(4) -0.0901(3) 0.9016(3) 0.0421(8) Uani 1 1 d . . . . .
H18 H 0.298149 -0.172722 0.933474 0.051 Uiso 1 1 calc R U . . .
C19 C 0.0996(4) -0.0702(3) 0.8894(3) 0.0411(8) Uani 1 1 d . . . . .
H19 H 0.063639 -0.138924 0.913635 0.049 Uiso 1 1 calc R U . . .
C20 C 0.0134(4) 0.0489(3) 0.8423(3) 0.0369(8) Uani 1 1 d . . . . .
H20 H -0.082598 0.062532 0.835105 0.044 Uiso 1 1 calc R U . . .
C21 C 0.0665(3) 0.1499(3) 0.8049(3) 0.0294(7) Uani 1 1 d . . . . .
H21 H 0.006998 0.232234 0.771170 0.035 Uiso 1 1 calc R U . . .
C22 C 0.1976(3) 0.4091(3) 0.9150(3) 0.0309(7) Uani 1 1 d . . . . .
C23 C 0.0677(4) 0.4546(3) 0.8689(3) 0.0393(8) Uani 1 1 d . . . . .
H23 H 0.021460 0.399188 0.872559 0.047 Uiso 1 1 calc R U . . .
C24 C 0.0068(4) 0.5816(4) 0.8177(4) 0.0482(9) Uani 1 1 d . . . . .
H24 H -0.081435 0.613817 0.785056 0.058 Uiso 1 1 calc R U . . .
C25 C 0.0736(4) 0.6623(3) 0.8137(3) 0.0453(9) Uani 1 1 d . . . . .
H25 H 0.030665 0.749458 0.779369 0.054 Uiso 1 1 calc R U . . .
C26 C 0.2028(4) 0.6159(3) 0.8596(3) 0.0401(8) Uani 1 1 d . . . . .
H26 H 0.248544 0.671387 0.856643 0.048 Uiso 1 1 calc R U . . .
C27 C 0.2657(3) 0.4898(3) 0.9097(3) 0.0337(7) Uani 1 1 d . . . . .
H27 H 0.354945 0.458117 0.940522 0.040 Uiso 1 1 calc R U . . .
Br1 Br 0.40364(4) 0.35815(4) 0.19606(4) 0.03756(15) Uani 0.8395(17) 1 d . . P B
1
C28 C 0.3241(2) 0.62558(18) 0.15204(17) 0.0610(7) Uani 0.8395(17) 1 d . . P B 1
H28A H 0.234053 0.643728 0.122776 0.091 Uiso 0.8395(17) 1 calc R U P B 1
H28B H 0.397140 0.633234 0.087021 0.091 Uiso 0.8395(17) 1 calc R U P B 1
H28C H 0.317587 0.684634 0.183426 0.091 Uiso 0.8395(17) 1 calc R U P B 1
C28' C 0.40364(4) 0.35815(4) 0.19606(4) 0.03756(15) Uani 0.1605(17) 1 d . . P B
2
H28D H 0.419244 0.273936 0.260280 0.056 Uiso 0.1605(17) 1 calc R U P B 2
H28E H 0.487405 0.363844 0.141230 0.056 Uiso 0.1605(17) 1 calc R U P B 2
H28F H 0.323548 0.376542 0.153626 0.056 Uiso 0.1605(17) 1 calc R U P B 2
Br1' Br 0.3241(2) 0.62558(18) 0.15204(17) 0.0610(7) Uani 0.1605(17) 1 d . . P B
2
N1 N 0.3559(3) 0.2236(2) 0.8542(2) 0.0291(6) Uani 1 1 d . . . . .
H1 H 0.447538 0.203948 0.840905 0.035 Uiso 1 1 calc R U . . .
N2 N 0.2759(2) 0.3594(2) 0.4619(2) 0.0246(5) Uani 1 1 d . . . . .
O1 O 0.3970(3) 0.2235(2) 1.0362(2) 0.0417(6) Uani 1 1 d . . . . .
O2 O 0.1796(3) 0.1817(2) 1.0272(2) 0.0441(6) Uani 1 1 d . . . . .
O3 O 0.4165(2) 0.4273(2) 0.6733(2) 0.0362(5) Uani 1 1 d . . . . .
O4 O 0.2411(2) 0.53952(19) 0.5523(2) 0.0327(5) Uani 1 1 d . . . . .
O5 O 0.4168(2) 0.28944(17) 0.47974(17) 0.0243(4) Uani 1 1 d . . . . .
O6 O 0.1260(2) 0.5268(2) 0.33835(19) 0.0334(5) Uani 1 1 d . . . . .
S1 S 0.28272(9) 0.24831(7) 0.97242(6) 0.03171(19) 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 1.382(5) . ?
C1 C6 1.391(4) . ?
C1 H1A 0.9500 . ?
C2 C3 1.385(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.500(4) . ?
C7 O5 1.456(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O6 1.221(4) . ?
C8 N2 1.353(4) . ?
C8 C9 1.521(4) . ?
C9 Br1' 1.709(3) . ?
C9 C28 1.709(3) . ?
C9 Br1 1.946(3) . ?
C9 C28' 1.946(3) . ?
C9 H9 1.0000 . ?
C10 N2 1.464(4) . ?
C10 C11 1.505(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.352(4) . ?
C11 C12 1.487(4) . ?
C12 O3 1.213(4) . ?
C12 O4 1.327(4) . ?
C13 O4 1.461(3) . ?
C13 C14 1.495(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 N1 1.428(4) . ?
C15 C16 1.484(4) . ?
C16 C21 1.388(4) . ?
C16 C17 1.398(4) . ?
C17 C18 1.377(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.373(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.394(4) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.388(5) . ?
C22 C23 1.390(5) . ?
C22 S1 1.763(3) . ?
C23 C24 1.382(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.376(5) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C28' H28D 0.9800 . ?
C28' H28E 0.9800 . ?
C28' H28F 0.9800 . ?
N1 S1 1.655(3) . ?
N1 H1 0.8800 . ?
N2 O5 1.407(3) . ?
O1 S1 1.430(2) . ?
O2 S1 1.428(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 C6 120.7(3) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 C3 119.9(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 121.4(3) . . ?
C1 C6 C7 119.5(3) . . ?
O5 C7 C6 108.4(2) . . ?
O5 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
O5 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
O6 C8 N2 121.3(3) . . ?
O6 C8 C9 122.3(3) . . ?
N2 C8 C9 116.4(3) . . ?
C8 C9 Br1' 110.6(2) . . ?
C8 C9 C28 110.6(2) . . ?
C8 C9 Br1 108.6(2) . . ?
C28 C9 Br1 109.92(18) . . ?
C8 C9 C28' 108.6(2) . . ?
Br1' C9 C28' 109.92(18) . . ?
C8 C9 H9 109.2 . . ?
C28 C9 H9 109.2 . . ?
Br1 C9 H9 109.2 . . ?
N2 C10 C11 110.1(2) . . ?
N2 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
N2 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.2 . . ?
C15 C11 C12 120.4(3) . . ?
C15 C11 C10 123.7(3) . . ?
C12 C11 C10 115.8(2) . . ?
O3 C12 O4 123.8(3) . . ?
O3 C12 C11 125.8(3) . . ?
O4 C12 C11 110.4(3) . . ?
O4 C13 C14 105.5(3) . . ?
O4 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
O4 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 N1 120.5(3) . . ?
C11 C15 C16 124.3(3) . . ?
N1 C15 C16 115.0(2) . . ?
C21 C16 C17 119.3(3) . . ?
C21 C16 C15 122.1(3) . . ?
C17 C16 C15 118.6(3) . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 120.1(3) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C27 C22 C23 120.7(3) . . ?
C27 C22 S1 119.2(2) . . ?
C23 C22 S1 120.0(3) . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.4 . . ?
C22 C23 H23 120.4 . . ?
C23 C24 C25 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 119.9(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C27 C26 C25 120.4(3) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C26 C27 C22 119.5(3) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 H27 120.2 . . ?
C9 C28 H28A 109.5 . . ?
C9 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C9 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C9 C28' H28D 109.5 . . ?
C9 C28' H28E 109.5 . . ?
H28D C28' H28E 109.5 . . ?
C9 C28' H28F 109.5 . . ?
H28D C28' H28F 109.5 . . ?
H28E C28' H28F 109.5 . . ?
C15 N1 S1 119.4(2) . . ?
C15 N1 H1 120.3 . . ?
S1 N1 H1 120.3 . . ?
C8 N2 O5 118.5(2) . . ?
C8 N2 C10 124.2(2) . . ?
O5 N2 C10 115.2(2) . . ?
C12 O4 C13 116.9(2) . . ?
N2 O5 C7 108.4(2) . . ?
O2 S1 O1 120.63(15) . . ?
O2 S1 N1 108.01(14) . . ?
O1 S1 N1 105.33(14) . . ?
O2 S1 C22 108.78(16) . . ?
O1 S1 C22 108.55(15) . . ?
N1 S1 C22 104.34(14) . . ?

_refine_diff_density_max         0.546
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.060

