# Electronic Supplementary Material (ESI) for ChemComm.
# 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_21SRA006
_database_code_depnum_ccdc_archive 'CCDC 2108910'
loop_
_audit_author_name
_audit_author_address
'Antonio L. Llamas-Saiz'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2021-09-09 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            cs1av_2l
_chemical_formula_moiety         'C18 H18 Br N O3 S'
_chemical_formula_sum            'C18 H18 Br N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         408.30

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.3536(8)
_cell_length_b                   9.6592(7)
_cell_length_c                   16.8001(12)
_cell_angle_alpha                90
_cell_angle_beta                 107.174(3)
_cell_angle_gamma                90
_cell_volume                     1760.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.4609
_cell_measurement_theta_max      29.8443
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.081
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
'TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1'
_exptl_absorpt_correction_T_min  0.651703
_exptl_absorpt_correction_T_max  0.746070

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-III C14'
_diffrn_measurement_method       'φ or ω oscillation scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            288564
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;

Refined as a 2-component twin.
;

_reflns_number_total             5431
_reflns_number_gt                4684
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1572
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.055
_refine_ls_number_reflns         5431
_refine_ls_number_parameters     220
_refine_ls_number_restraints     181
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+4.7000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         2.041
_refine_diff_density_min         -1.332
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP 2014.1 (Farrugia, 2012)'
_computing_publication_material  'IUCr Journals printCIF'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.60085(4) 0.07771(4) 0.60696(3) 0.04630(15) Uani d . . . 1 . .
N N1 0.2694(2) 0.4701(3) 0.50096(15) 0.0226(5) Uani d . . . 1 . .
C C2 0.2923(3) 0.6169(4) 0.5225(2) 0.0309(7) Uani d . . . 1 . .
H H2A 0.279846 0.670693 0.470491 0.037000 Uiso calc U . R 1 . .
H H2B 0.379448 0.628185 0.556059 0.037000 Uiso calc U . R 1 . .
C C3 0.2107(4) 0.6766(5) 0.5705(2) 0.0450(10) Uani d . . . 1 . .
H H3 0.122354 0.668302 0.536635 0.054000 Uiso calc U . R 1 . .
O O4 0.2288(3) 0.6093(4) 0.64886(18) 0.0485(8) Uani d . . . 1 . .
C C5 0.1896(4) 0.4672(6) 0.6449(3) 0.0461(10) Uani d . . . 1 . .
H H5A 0.114283 0.456059 0.597192 0.055000 Uiso calc U . R 1 . .
H H5B 0.167787 0.444710 0.696296 0.055000 Uiso calc U . R 1 . .
C C6 0.2860(3) 0.3652(4) 0.63549(19) 0.0301(7) Uani d . . . 1 . .
C C7 0.3410(4) 0.2692(5) 0.6970(2) 0.0395(9) Uani d . . . 1 . .
H H7 0.316045 0.265473 0.746164 0.047000 Uiso calc U . R 1 . .
C C8 0.4309(4) 0.1794(4) 0.6884(2) 0.0398(9) Uani d . . . 1 . .
H H8 0.466355 0.113039 0.730296 0.048000 Uiso calc U . R 1 . .
C C9 0.4683(3) 0.1882(4) 0.6174(2) 0.0302(7) Uani d . . . 1 . .
C C10 0.4161(3) 0.2823(3) 0.55445(18) 0.0238(6) Uani d . . . 1 . .
H H10 0.443114 0.286962 0.506111 0.029000 Uiso calc U . R 1 . .
C C11 0.3242(3) 0.3690(3) 0.56347(17) 0.0223(5) Uani d . . . 1 . .
C C12 0.2453(4) 0.8325(6) 0.5866(3) 0.0541(12) Uani d . . . 1 . .
H H12 0.325264 0.854141 0.621948 0.065000 Uiso calc U . R 1 . .
C C13 0.1745(6) 0.9314(7) 0.5559(4) 0.0752(19) Uani d . . . 1 . .
H H13A 0.093868 0.913451 0.520223 0.090000 Uiso calc U . R 1 . .
H H13B 0.201573 1.024148 0.568286 0.090000 Uiso calc U . R 1 . .
S S21 0.18974(6) 0.42290(8) 0.40720(4) 0.02196(16) Uani d . . . 1 . .
O O22 0.1058(2) 0.5343(3) 0.37429(14) 0.0302(5) Uani d . . . 1 . .
O O23 0.1443(2) 0.2863(3) 0.41368(14) 0.0303(5) Uani d . . . 1 . .
C C24 0.2913(2) 0.4127(3) 0.34554(16) 0.0188(5) Uani d . . . 1 . .
C C25 0.3200(3) 0.5322(3) 0.30898(18) 0.0223(5) Uani d . . . 1 . .
H H25 0.289567 0.619653 0.319718 0.027000 Uiso calc U . R 1 . .
C C26 0.3942(3) 0.5215(3) 0.25629(19) 0.0242(6) Uani d . . . 1 . .
H H26 0.413439 0.602444 0.230470 0.029000 Uiso calc U . R 1 . .
C C27 0.4406(3) 0.3942(4) 0.24097(19) 0.0250(6) Uani d . . . 1 . .
C C28 0.4126(3) 0.2771(3) 0.2801(2) 0.0277(6) Uani d . . . 1 . .
H H28 0.445285 0.189910 0.271053 0.033000 Uiso calc U . R 1 . .
C C29 0.3377(3) 0.2853(3) 0.33203(19) 0.0240(6) Uani d . . . 1 . .
H H29 0.318576 0.204411 0.357952 0.029000 Uiso calc U . R 1 . .
C C30 0.5178(4) 0.3839(5) 0.1819(2) 0.0384(8) Uani d . . . 1 . .
H H30A 0.496119 0.299244 0.148656 0.058000 Uiso calc U . R 1 . .
H H30B 0.605280 0.381176 0.213881 0.058000 Uiso calc U . R 1 . .
H H30C 0.502171 0.464559 0.144896 0.058000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.895(4) ?
N1 C11 . 1.434(4) ?
N1 C2 . 1.468(4) ?
N1 S21 . 1.633(3) ?
C2 C3 . 1.511(5) ?
C2 H2A . 0.990000 ?
C2 H2B . 0.990000 ?
C3 O4 . 1.427(5) ?
C3 C12 . 1.559(7) ?
C3 H3 . 1.000000 ?
O4 C5 . 1.438(6) ?
C5 C6 . 1.515(6) ?
C5 H5A . 0.990000 ?
C5 H5B . 0.990000 ?
C6 C7 . 1.391(5) ?
C6 C11 . 1.401(4) ?
C7 C8 . 1.379(7) ?
C7 H7 . 0.950000 ?
C8 C9 . 1.381(5) ?
C8 H8 . 0.950000 ?
C9 C10 . 1.387(4) ?
C10 C11 . 1.381(4) ?
C10 H10 . 0.950000 ?
C12 C13 . 1.258(8) ?
C12 H12 . 0.950000 ?
C13 H13A . 0.950000 ?
C13 H13B . 0.950000 ?
S21 O23 . 1.432(3) ?
S21 O22 . 1.436(2) ?
S21 C24 . 1.766(3) ?
C24 C29 . 1.384(4) ?
C24 C25 . 1.390(4) ?
C25 C26 . 1.394(4) ?
C25 H25 . 0.950000 ?
C26 C27 . 1.391(5) ?
C26 H26 . 0.950000 ?
C27 C28 . 1.392(5) ?
C27 C30 . 1.509(4) ?
C28 C29 . 1.389(4) ?
C28 H28 . 0.950000 ?
C29 H29 . 0.950000 ?
C30 H30A . 0.980000 ?
C30 H30B . 0.980000 ?
C30 H30C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 C2 . . 118.1(2) ?
C11 N1 S21 . . 120.9(2) ?
C2 N1 S21 . . 121.0(2) ?
N1 C2 C3 . . 114.1(3) ?
N1 C2 H2A . . 108.700000 ?
C3 C2 H2A . . 108.700000 ?
N1 C2 H2B . . 108.700000 ?
C3 C2 H2B . . 108.700000 ?
H2A C2 H2B . . 107.600000 ?
O4 C3 C2 . . 112.0(3) ?
O4 C3 C12 . . 108.7(3) ?
C2 C3 C12 . . 107.4(4) ?
O4 C3 H3 . . 109.600000 ?
C2 C3 H3 . . 109.600000 ?
C12 C3 H3 . . 109.600000 ?
C3 O4 C5 . . 115.7(3) ?
O4 C5 C6 . . 113.7(3) ?
O4 C5 H5A . . 108.800000 ?
C6 C5 H5A . . 108.800000 ?
O4 C5 H5B . . 108.800000 ?
C6 C5 H5B . . 108.800000 ?
H5A C5 H5B . . 107.700000 ?
C7 C6 C11 . . 118.2(3) ?
C7 C6 C5 . . 122.4(3) ?
C11 C6 C5 . . 119.4(3) ?
C8 C7 C6 . . 121.6(3) ?
C8 C7 H7 . . 119.200000 ?
C6 C7 H7 . . 119.200000 ?
C7 C8 C9 . . 118.5(3) ?
C7 C8 H8 . . 120.700000 ?
C9 C8 H8 . . 120.700000 ?
C8 C9 C10 . . 121.8(4) ?
C8 C9 Br1 . . 120.0(3) ?
C10 C9 Br1 . . 118.1(3) ?
C11 C10 C9 . . 118.7(3) ?
C11 C10 H10 . . 120.700000 ?
C9 C10 H10 . . 120.700000 ?
C10 C11 C6 . . 121.0(3) ?
C10 C11 N1 . . 120.7(3) ?
C6 C11 N1 . . 118.2(3) ?
C13 C12 C3 . . 124.4(5) ?
C13 C12 H12 . . 117.800000 ?
C3 C12 H12 . . 117.800000 ?
C12 C13 H13A . . 120.000000 ?
C12 C13 H13B . . 120.000000 ?
H13A C13 H13B . . 120.000000 ?
O23 S21 O22 . . 120.44(15) ?
O23 S21 N1 . . 107.05(14) ?
O22 S21 N1 . . 106.14(14) ?
O23 S21 C24 . . 107.81(14) ?
O22 S21 C24 . . 106.85(14) ?
N1 S21 C24 . . 108.04(13) ?
C29 C24 C25 . . 121.1(3) ?
C29 C24 S21 . . 119.4(2) ?
C25 C24 S21 . . 119.5(2) ?
C24 C25 C26 . . 118.9(3) ?
C24 C25 H25 . . 120.500000 ?
C26 C25 H25 . . 120.500000 ?
C27 C26 C25 . . 121.0(3) ?
C27 C26 H26 . . 119.500000 ?
C25 C26 H26 . . 119.500000 ?
C26 C27 C28 . . 118.7(3) ?
C26 C27 C30 . . 120.3(3) ?
C28 C27 C30 . . 121.0(3) ?
C29 C28 C27 . . 121.2(3) ?
C29 C28 H28 . . 119.400000 ?
C27 C28 H28 . . 119.400000 ?
C24 C29 C28 . . 119.1(3) ?
C24 C29 H29 . . 120.400000 ?
C28 C29 H29 . . 120.400000 ?
C27 C30 H30A . . 109.500000 ?
C27 C30 H30B . . 109.500000 ?
H30A C30 H30B . . 109.500000 ?
C27 C30 H30C . . 109.500000 ?
H30A C30 H30C . . 109.500000 ?
H30B C30 H30C . . 109.500000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C2 C3 . . . . -81.3(4) ?
S21 N1 C2 C3 . . . . 101.7(3) ?
N1 C2 C3 O4 . . . . 61.8(4) ?
N1 C2 C3 C12 . . . . -179.0(3) ?
C2 C3 O4 C5 . . . . -67.4(5) ?
C12 C3 O4 C5 . . . . 174.2(3) ?
C3 O4 C5 C6 . . . . 85.6(4) ?
O4 C5 C6 C7 . . . . 114.6(4) ?
O4 C5 C6 C11 . . . . -63.8(4) ?
C11 C6 C7 C8 . . . . 0.0(5) ?
C5 C6 C7 C8 . . . . -178.3(4) ?
C6 C7 C8 C9 . . . . 1.4(5) ?
C7 C8 C9 C10 . . . . -1.4(5) ?
C7 C8 C9 Br1 . . . . 174.8(3) ?
C8 C9 C10 C11 . . . . -0.1(5) ?
Br1 C9 C10 C11 . . . . -176.3(2) ?
C9 C10 C11 C6 . . . . 1.7(5) ?
C9 C10 C11 N1 . . . . 178.6(3) ?
C7 C6 C11 C10 . . . . -1.6(5) ?
C5 C6 C11 C10 . . . . 176.8(3) ?
C7 C6 C11 N1 . . . . -178.6(3) ?
C5 C6 C11 N1 . . . . -0.2(5) ?
C2 N1 C11 C10 . . . . -112.3(3) ?
S21 N1 C11 C10 . . . . 64.6(4) ?
C2 N1 C11 C6 . . . . 64.7(4) ?
S21 N1 C11 C6 . . . . -118.3(3) ?
O4 C3 C12 C13 . . . . -124.6(6) ?
C2 C3 C12 C13 . . . . 114.0(6) ?
C11 N1 S21 O23 . . . . 24.8(3) ?
C2 N1 S21 O23 . . . . -158.3(2) ?
C11 N1 S21 O22 . . . . 154.6(2) ?
C2 N1 S21 O22 . . . . -28.5(3) ?
C11 N1 S21 C24 . . . . -91.1(2) ?
C2 N1 S21 C24 . . . . 85.8(3) ?
O23 S21 C24 C29 . . . . -16.7(3) ?
O22 S21 C24 C29 . . . . -147.5(2) ?
N1 S21 C24 C29 . . . . 98.7(3) ?
O23 S21 C24 C25 . . . . 161.1(2) ?
O22 S21 C24 C25 . . . . 30.3(3) ?
N1 S21 C24 C25 . . . . -83.5(2) ?
C29 C24 C25 C26 . . . . 1.7(4) ?
S21 C24 C25 C26 . . . . -176.1(2) ?
C24 C25 C26 C27 . . . . -0.8(4) ?
C25 C26 C27 C28 . . . . -0.7(5) ?
C25 C26 C27 C30 . . . . 178.3(3) ?
C26 C27 C28 C29 . . . . 1.4(5) ?
C30 C27 C28 C29 . . . . -177.5(3) ?
C25 C24 C29 C28 . . . . -1.0(4) ?
S21 C24 C29 C28 . . . . 176.8(2) ?
C27 C28 C29 C24 . . . . -0.6(5) ?

####################################################################### 
# 
# 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_21SRA007
_database_code_depnum_ccdc_archive 'CCDC 2108911'
loop_
_audit_author_name
_audit_author_address
'Antonio L. Llamas-Saiz'
;Universidade de Santiago de Compostela
Spain
;
_audit_update_record             
;
2021-09-09 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            cs1av_2o
_chemical_formula_moiety         'C20 H23 N O5 S'
_chemical_formula_sum            'C20 H23 N O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         389.45

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.3804(8)
_cell_length_b                   23.7391(19)
_cell_length_c                   9.4372(7)
_cell_angle_alpha                90
_cell_angle_beta                 114.324(3)
_cell_angle_gamma                90
_cell_volume                     1914.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9818
_cell_measurement_theta_min      2.3827
_cell_measurement_theta_max      28.0471
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_power             ?
_diffrn_source_current           ?
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON-III C14'
_diffrn_measurement_method       'φ or ω oscillation scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            73538
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         28.39
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             4842
_reflns_number_gt                4364
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.1292
_refine_ls_wR_factor_gt          0.2387
_refine_ls_wR_factor_ref         0.2431
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_restrained_S_all      1.229
_refine_ls_number_reflns         4842
_refine_ls_number_parameters     267
_refine_ls_number_restraints     226
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+12.0839P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.879
_refine_diff_density_min         -0.696
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX3 software'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP 2014.1 (Farrugia, 2012)'
_computing_publication_material  'IUCr Journals printCIF'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.5212(5) 0.60768(18) 0.7627(5) 0.0304(9) Uani d . . . 1.000000 . .
C C2 0.6809(7) 0.6243(3) 0.7873(7) 0.0389(14) Uani d . . . 1.000000 . .
H H2A 0.684721 0.665816 0.778673 0.047000 Uiso calc U . R 1.000000 . .
H H2B 0.705494 0.607680 0.703759 0.047000 Uiso calc U . R 1.000000 . .
C C3 0.8062(8) 0.6060(3) 0.9448(8) 0.0554(19) Uani d . . . 1.000000 . .
H H3A 0.763265 0.618504 1.020693 0.066000 Uiso calc U P R 0.48(3) A 1
H H3B 0.795831 0.625840 1.033627 0.066000 Uiso calc U P R 0.52(3) A 2
O O4 0.8235(5) 0.5482(2) 0.9677(5) 0.0448(11) Uani d . . . 1.000000 . .
C C5 0.6934(6) 0.5203(2) 0.9766(6) 0.0248(10) Uani d . . . 1.000000 . .
H H5A 0.651511 0.544103 1.036805 0.030000 Uiso calc U . R 1.000000 . .
H H5B 0.729782 0.484520 1.034281 0.030000 Uiso calc U . R 1.000000 . .
C C6 0.5636(5) 0.5076(2) 0.8212(5) 0.0212(9) Uani d . . . 1.000000 . .
C C7 0.5279(5) 0.45167(19) 0.7735(5) 0.0195(9) Uani d . . . 1.000000 . .
H H7 0.592095 0.422285 0.835661 0.023000 Uiso calc U . R 1.000000 . .
C C8 0.4005(6) 0.4384(2) 0.6369(6) 0.0227(9) Uani d . . . 1.000000 . .
C C9 0.3064(6) 0.4822(2) 0.5443(6) 0.0265(10) Uani d . . . 1.000000 . .
C C10 0.3489(6) 0.5374(2) 0.5849(6) 0.0258(10) Uani d . . . 1.000000 . .
H H10 0.291152 0.567055 0.518353 0.031000 Uiso calc U . R 1.000000 . .
C C11 0.4768(6) 0.5499(2) 0.7239(6) 0.0224(9) Uani d . . . 1.000000 . .
C C12 0.9465(15) 0.6408(8) 0.9839(17) 0.036(4) Uani d . P . 0.48(3) A 1
H H12 0.940467 0.680797 0.981279 0.043000 Uiso calc U P R 0.48(3) A 1
C C13 1.0786(16) 0.6151(9) 1.0221(18) 0.035(4) Uani d . P . 0.48(3) A 1
H H13A 1.082262 0.575144 1.024132 0.042000 Uiso calc U P R 0.48(3) A 1
H H13B 1.172073 0.636246 1.048261 0.042000 Uiso calc U P R 0.48(3) A 1
C C12B 0.9769(15) 0.6170(6) 0.9402(15) 0.030(3) Uani d . P . 0.52(3) A 2
H H12B 0.995704 0.605431 0.853088 0.036000 Uiso calc U P R 0.52(3) A 2
C C13B 1.0861(16) 0.6418(8) 1.0578(18) 0.038(3) Uani d . P . 0.52(3) A 2
H H13C 1.066414 0.653296 1.144461 0.046000 Uiso calc U P R 0.52(3) A 2
H H13D 1.185633 0.648504 1.056908 0.046000 Uiso calc U P R 0.52(3) A 2
O O14 0.3583(5) 0.38470(15) 0.5849(4) 0.0321(9) Uani d . . . 1.000000 . .
C C15 0.4624(7) 0.3403(2) 0.6641(7) 0.0362(13) Uani d . . . 1.000000 . .
H H15A 0.419754 0.304385 0.612988 0.054000 Uiso calc U . R 1.000000 . .
H H15B 0.474925 0.338933 0.772349 0.054000 Uiso calc U . R 1.000000 . .
H H15C 0.564395 0.346973 0.661398 0.054000 Uiso calc U . R 1.000000 . .
O O16 0.1803(5) 0.46504(17) 0.4165(5) 0.0427(11) Uani d . . . 1.000000 . .
C C17 0.0833(8) 0.5086(3) 0.3188(9) 0.062(2) Uani d . . . 1.000000 . .
H H17A 0.146934 0.533524 0.285329 0.093000 Uiso calc U . R 1.000000 . .
H H17B 0.036557 0.530443 0.376893 0.093000 Uiso calc U . R 1.000000 . .
H H17C 0.000274 0.491628 0.227343 0.093000 Uiso calc U . R 1.000000 . .
S S21 0.4118(2) 0.64880(6) 0.81437(16) 0.0374(4) Uani d . . . 1.000000 . .
O O22 0.5042(7) 0.69673(19) 0.8859(5) 0.0635(16) Uani d . . . 1.000000 . .
O O23 0.3417(8) 0.6166(2) 0.8971(6) 0.0705(19) Uani d . . . 1.000000 . .
C C24 0.2573(6) 0.6718(2) 0.6431(6) 0.0256(10) Uani d . . . 1.000000 . .
C C25 0.2831(6) 0.7134(2) 0.5538(6) 0.0269(10) Uani d . . . 1.000000 . .
H H25 0.384587 0.728915 0.582713 0.032000 Uiso calc U . R 1.000000 . .
C C26 0.1595(7) 0.7321(3) 0.4227(7) 0.0388(13) Uani d . . . 1.000000 . .
H H26 0.177212 0.761131 0.362560 0.047000 Uiso calc U . R 1.000000 . .
C C27 0.0111(8) 0.7103(3) 0.3754(9) 0.0509(16) Uani d . . . 1.000000 . .
C C28 -0.0108(8) 0.6677(3) 0.4615(11) 0.0606(19) Uani d . . . 1.000000 . .
H H28 -0.111531 0.651088 0.428701 0.073000 Uiso calc U . R 1.000000 . .
C C29 0.1103(8) 0.6480(3) 0.5960(9) 0.0476(16) Uani d . . . 1.000000 . .
H H29 0.092364 0.618520 0.654839 0.057000 Uiso calc U . R 1.000000 . .
C C30 -0.1216(11) 0.7339(4) 0.2326(11) 0.082(3) Uani d U . . 1.000000 . .
H H30A -0.108067 0.722422 0.139215 0.123000 Uiso calc U . R 1.000000 . .
H H30B -0.121122 0.775125 0.238946 0.123000 Uiso calc U . R 1.000000 . .
H H30C -0.221525 0.719455 0.227450 0.123000 Uiso calc U . R 1.000000 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C11 . 1.436(6) ?
N1 C2 . 1.473(7) ?
N1 S21 . 1.630(5) ?
C2 C3 . 1.530(8) ?
C2 H2A . 0.990000 ?
C2 H2B . 0.990000 ?
C3 O4 . 1.390(9) ?
C3 C12 . 1.466(13) ?
C3 C12B . 1.641(14) ?
C3 H3A . 1.000000 ?
C3 H3B . 1.000000 ?
O4 C5 . 1.421(6) ?
C5 C6 . 1.502(7) ?
C5 H5A . 0.990000 ?
C5 H5B . 0.990000 ?
C6 C11 . 1.379(7) ?
C6 C7 . 1.397(7) ?
C7 C8 . 1.386(7) ?
C7 H7 . 0.950000 ?
C8 O14 . 1.364(6) ?
C8 C9 . 1.412(7) ?
C9 O16 . 1.358(6) ?
C9 C10 . 1.377(7) ?
C10 C11 . 1.397(7) ?
C10 H10 . 0.950000 ?
C12 C13 . 1.29(3) ?
C12 H12 . 0.950000 ?
C13 H13A . 0.950000 ?
C13 H13B . 0.950000 ?
C12B C13B . 1.30(2) ?
C12B H12B . 0.950000 ?
C13B H13C . 0.950000 ?
C13B H13D . 0.950000 ?
O14 C15 . 1.422(6) ?
C15 H15A . 0.980000 ?
C15 H15B . 0.980000 ?
C15 H15C . 0.980000 ?
O16 C17 . 1.434(7) ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
S21 O22 . 1.421(5) ?
S21 O23 . 1.432(5) ?
S21 C24 . 1.755(6) ?
C24 C29 . 1.383(8) ?
C24 C25 . 1.383(6) ?
C25 C26 . 1.375(8) ?
C25 H25 . 0.950000 ?
C26 C27 . 1.376(9) ?
C26 H26 . 0.950000 ?
C27 C28 . 1.365(11) ?
C27 C30 . 1.516(11) ?
C28 C29 . 1.391(11) ?
C28 H28 . 0.950000 ?
C29 H29 . 0.950000 ?
C30 H30A . 0.980000 ?
C30 H30B . 0.980000 ?
C30 H30C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 C2 . . 117.8(4) ?
C11 N1 S21 . . 119.7(4) ?
C2 N1 S21 . . 121.1(4) ?
N1 C2 C3 . . 113.7(5) ?
N1 C2 H2A . . 108.800000 ?
C3 C2 H2A . . 108.800000 ?
N1 C2 H2B . . 108.800000 ?
C3 C2 H2B . . 108.800000 ?
H2A C2 H2B . . 107.700000 ?
O4 C3 C12 . . 118.8(9) ?
O4 C3 C2 . . 115.2(6) ?
C12 C3 C2 . . 109.6(6) ?
O4 C3 C12B . . 96.2(7) ?
C2 C3 C12B . . 107.3(6) ?
O4 C3 H3A . . 103.700000 ?
C12 C3 H3A . . 103.700000 ?
C2 C3 H3A . . 103.700000 ?
O4 C3 H3B . . 112.300000 ?
C2 C3 H3B . . 112.300000 ?
C12B C3 H3B . . 112.300000 ?
C3 O4 C5 . . 114.9(5) ?
O4 C5 C6 . . 113.9(4) ?
O4 C5 H5A . . 108.800000 ?
C6 C5 H5A . . 108.800000 ?
O4 C5 H5B . . 108.800000 ?
C6 C5 H5B . . 108.800000 ?
H5A C5 H5B . . 107.700000 ?
C11 C6 C7 . . 118.7(4) ?
C11 C6 C5 . . 121.5(4) ?
C7 C6 C5 . . 119.8(4) ?
C8 C7 C6 . . 121.1(4) ?
C8 C7 H7 . . 119.400000 ?
C6 C7 H7 . . 119.400000 ?
O14 C8 C7 . . 124.0(4) ?
O14 C8 C9 . . 116.8(4) ?
C7 C8 C9 . . 119.2(4) ?
O16 C9 C10 . . 125.4(5) ?
O16 C9 C8 . . 114.9(5) ?
C10 C9 C8 . . 119.6(5) ?
C9 C10 C11 . . 120.1(4) ?
C9 C10 H10 . . 120.000000 ?
C11 C10 H10 . . 120.000000 ?
C6 C11 C10 . . 120.9(4) ?
C6 C11 N1 . . 119.8(4) ?
C10 C11 N1 . . 119.2(4) ?
C13 C12 C3 . . 117.5(18) ?
C13 C12 H12 . . 121.200000 ?
C3 C12 H12 . . 121.200000 ?
C12 C13 H13A . . 120.000000 ?
C12 C13 H13B . . 120.000000 ?
H13A C13 H13B . . 120.000000 ?
C13B C12B C3 . . 119.0(12) ?
C13B C12B H12B . . 120.500000 ?
C3 C12B H12B . . 120.500000 ?
C12B C13B H13C . . 120.000000 ?
C12B C13B H13D . . 120.000000 ?
H13C C13B H13D . . 120.000000 ?
C8 O14 C15 . . 117.9(4) ?
O14 C15 H15A . . 109.500000 ?
O14 C15 H15B . . 109.500000 ?
H15A C15 H15B . . 109.500000 ?
O14 C15 H15C . . 109.500000 ?
H15A C15 H15C . . 109.500000 ?
H15B C15 H15C . . 109.500000 ?
C9 O16 C17 . . 116.4(5) ?
O16 C17 H17A . . 109.500000 ?
O16 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
O16 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
O22 S21 O23 . . 119.7(4) ?
O22 S21 N1 . . 106.6(3) ?
O23 S21 N1 . . 109.3(2) ?
O22 S21 C24 . . 107.4(3) ?
O23 S21 C24 . . 106.1(3) ?
N1 S21 C24 . . 107.1(2) ?
C29 C24 C25 . . 119.8(5) ?
C29 C24 S21 . . 120.3(4) ?
C25 C24 S21 . . 119.9(4) ?
C26 C25 C24 . . 119.0(5) ?
C26 C25 H25 . . 120.500000 ?
C24 C25 H25 . . 120.500000 ?
C25 C26 C27 . . 122.4(6) ?
C25 C26 H26 . . 118.800000 ?
C27 C26 H26 . . 118.800000 ?
C28 C27 C26 . . 117.8(7) ?
C28 C27 C30 . . 122.2(7) ?
C26 C27 C30 . . 120.0(8) ?
C27 C28 C29 . . 121.7(6) ?
C27 C28 H28 . . 119.100000 ?
C29 C28 H28 . . 119.100000 ?
C24 C29 C28 . . 119.2(6) ?
C24 C29 H29 . . 120.400000 ?
C28 C29 H29 . . 120.400000 ?
C27 C30 H30A . . 109.500000 ?
C27 C30 H30B . . 109.500000 ?
H30A C30 H30B . . 109.500000 ?
C27 C30 H30C . . 109.500000 ?
H30A C30 H30C . . 109.500000 ?
H30B C30 H30C . . 109.500000 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C2 C3 . . . . -76.9(7) ?
S21 N1 C2 C3 . . . . 89.8(6) ?
N1 C2 C3 O4 . . . . 63.9(9) ?
N1 C2 C3 C12 . . . . -159.0(11) ?
N1 C2 C3 C12B . . . . 169.6(7) ?
C12 C3 O4 C5 . . . . 160.3(9) ?
C2 C3 O4 C5 . . . . -66.8(8) ?
C12B C3 O4 C5 . . . . -179.2(6) ?
C3 O4 C5 C6 . . . . 81.7(6) ?
O4 C5 C6 C11 . . . . -66.9(6) ?
O4 C5 C6 C7 . . . . 113.7(5) ?
C11 C6 C7 C8 . . . . -5.0(7) ?
C5 C6 C7 C8 . . . . 174.4(4) ?
C6 C7 C8 O14 . . . . -179.2(4) ?
C6 C7 C8 C9 . . . . 0.6(7) ?
O14 C8 C9 O16 . . . . 2.6(7) ?
C7 C8 C9 O16 . . . . -177.2(5) ?
O14 C8 C9 C10 . . . . -175.6(5) ?
C7 C8 C9 C10 . . . . 4.6(7) ?
O16 C9 C10 C11 . . . . 176.6(5) ?
C8 C9 C10 C11 . . . . -5.4(8) ?
C7 C6 C11 C10 . . . . 4.2(7) ?
C5 C6 C11 C10 . . . . -175.1(4) ?
C7 C6 C11 N1 . . . . -173.6(4) ?
C5 C6 C11 N1 . . . . 7.1(7) ?
C9 C10 C11 C6 . . . . 0.9(8) ?
C9 C10 C11 N1 . . . . 178.7(5) ?
C2 N1 C11 C6 . . . . 56.5(6) ?
S21 N1 C11 C6 . . . . -110.4(5) ?
C2 N1 C11 C10 . . . . -121.4(5) ?
S21 N1 C11 C10 . . . . 71.7(6) ?
O4 C3 C12 C13 . . . . 7.(2) ?
C2 C3 C12 C13 . . . . -128.0(15) ?
O4 C3 C12B C13B . . . . -107.6(15) ?
C2 C3 C12B C13B . . . . 133.6(14) ?
C7 C8 O14 C15 . . . . -8.7(7) ?
C9 C8 O14 C15 . . . . 171.5(5) ?
C10 C9 O16 C17 . . . . -1.2(9) ?
C8 C9 O16 C17 . . . . -179.3(6) ?
C11 N1 S21 O22 . . . . 164.0(4) ?
C2 N1 S21 O22 . . . . -2.4(5) ?
C11 N1 S21 O23 . . . . 33.3(5) ?
C2 N1 S21 O23 . . . . -133.2(5) ?
C11 N1 S21 C24 . . . . -81.3(4) ?
C2 N1 S21 C24 . . . . 112.3(4) ?
O22 S21 C24 C29 . . . . -143.4(5) ?
O23 S21 C24 C29 . . . . -14.2(5) ?
N1 S21 C24 C29 . . . . 102.5(5) ?
O22 S21 C24 C25 . . . . 37.4(5) ?
O23 S21 C24 C25 . . . . 166.6(4) ?
N1 S21 C24 C25 . . . . -76.8(5) ?
C29 C24 C25 C26 . . . . 2.8(8) ?
S21 C24 C25 C26 . . . . -178.0(4) ?
C24 C25 C26 C27 . . . . -1.0(9) ?
C25 C26 C27 C28 . . . . -1.6(9) ?
C25 C26 C27 C30 . . . . 178.0(6) ?
C26 C27 C28 C29 . . . . 2.3(10) ?
C30 C27 C28 C29 . . . . -177.2(7) ?
C25 C24 C29 C28 . . . . -2.0(9) ?
S21 C24 C29 C28 . . . . 178.7(5) ?
C27 C28 C29 C24 . . . . -0.6(10) ?

