# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_rs057
_database_code_depnum_ccdc_archive 'CCDC 2083658'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;Molecular Education, Technology, and Research Innovation Center, North Carolina State University
United States of America
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            DC-004
_chemical_formula_moiety         'C6 H6 Br N O'
_chemical_formula_sum            'C6 H6 Br N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         188.03

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   11.2353(7)
_cell_length_b                   7.3127(5)
_cell_length_c                   15.8256(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.408(2)
_cell_angle_gamma                90
_cell_volume                     1300.20(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      5.5912
_cell_measurement_theta_max      72.9344
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.232
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.052
_exptl_crystal_density_diffrn    1.921
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736

_exptl_absorpt_coefficient_mu    7.888
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.68

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            19445
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         72.93
_diffrn_reflns_theta_full        72.93
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18

_refine_special_details          
;
;

_reflns_number_total             2562
_reflns_number_gt                2531
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0828
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_restrained_S_all      1.201
_refine_ls_number_reflns         2562
_refine_ls_number_parameters     171
_refine_ls_number_restraints     3
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0174P)²+5.1280P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_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         1.004
_refine_diff_density_min         -0.434
_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 0.0181 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'
Br Br -0.6763 1.2805 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

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_1 0.01127(3) 0.85143(5) 0.38442(2) 0.02104(13) Uani d . . . 1 . .
O O1_1 0.3160(2) 0.1667(4) 0.51914(16) 0.0225(5) Uani d . . . 1 . .
N N1_1 0.2672(3) 0.5569(4) 0.50150(18) 0.0166(6) Uani d . . D 1 . .
H H1_1 0.333(2) 0.553(6) 0.530(2) 0.02 Uiso d U . D 1 . .
C C1_1 0.2169(3) 0.7178(5) 0.4799(2) 0.0177(7) Uani d . . . 1 . .
H H1A_1 0.244059 0.835885 0.496009 0.021 Uiso calc U . R 1 . .
C C2_1 0.1185(3) 0.6794(5) 0.4301(2) 0.0180(7) Uani d . . . 1 . .
C C3_1 0.1087(3) 0.4898(5) 0.4196(2) 0.0168(7) Uani d . . . 1 . .
C C4_1 0.2037(3) 0.4153(5) 0.4653(2) 0.0170(7) Uani d . . . 1 . .
C C5_1 0.2332(3) 0.2277(5) 0.4767(2) 0.0197(7) Uani d . . . 1 . .
H H5_1 0.183962 0.141014 0.448539 0.024 Uiso calc U . R 1 . .
C C6_1 0.0150(3) 0.3907(5) 0.3695(2) 0.0192(7) Uani d . . . 1 . .
H H6A_1 0.021329 0.424334 0.309774 0.029 Uiso calc U . R 1 . .
H H6B_1 -0.063962 0.424599 0.390334 0.029 Uiso calc U . R 1 . .
H H6C_1 0.026328 0.258519 0.375698 0.029 Uiso calc U . R 1 . .
Br Br1_2 0.74440(3) -0.09463(5) 0.76141(2) 0.01978(12) Uani d . . . 1 . .
O O1_2 0.4753(2) 0.5988(3) 0.59987(16) 0.0201(5) Uani d . . . 1 . .
N N1_2 0.5177(3) 0.2090(4) 0.62180(18) 0.0166(6) Uani d . . D 1 . .
H H1_2 0.460(3) 0.235(6) 0.588(2) 0.02 Uiso d U . D 1 . .
C C1_2 0.5637(3) 0.0473(5) 0.6460(2) 0.0176(7) Uani d . . . 1 . .
H H1A_2 0.540344 -0.069624 0.625664 0.021 Uiso calc U . R 1 . .
C C2_2 0.6508(3) 0.0821(5) 0.7058(2) 0.0178(7) Uani d . . . 1 . .
C C3_2 0.6591(3) 0.2709(5) 0.7197(2) 0.0165(7) Uani d . . . 1 . .
C C4_2 0.5732(3) 0.3493(5) 0.6658(2) 0.0169(7) Uani d . . . 1 . .
C C5_2 0.5470(3) 0.5384(5) 0.6520(2) 0.0173(7) Uani d . . . 1 . .
H H5_2 0.58853 0.624878 0.685915 0.021 Uiso calc U . R 1 . .
C C6_2 0.7412(3) 0.3660(5) 0.7797(2) 0.0205(7) Uani d . . . 1 . .
H H6A_2 0.823786 0.340352 0.764193 0.031 Uiso calc U . R 1 . .
H H6B_2 0.726763 0.322159 0.837261 0.031 Uiso calc U . R 1 . .
H H6C_2 0.726925 0.498147 0.777155 0.031 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_1 C2_1 . 1.883(4) ?
O1_1 C5_1 . 1.228(4) ?
N1_1 C1_1 . 1.348(5) ?
N1_1 C4_1 . 1.380(4) ?
N1_1 H1_1 . 0.858(16) ?
C1_1 C2_1 . 1.382(5) ?
C1_1 H1A_1 . 0.95 ?
C2_1 C3_1 . 1.400(5) ?
C3_1 C4_1 . 1.396(5) ?
C3_1 C6_1 . 1.500(5) ?
C4_1 C5_1 . 1.423(5) ?
C5_1 H5_1 . 0.95 ?
C6_1 H6A_1 . 0.98 ?
C6_1 H6B_1 . 0.98 ?
C6_1 H6C_1 . 0.98 ?
Br1_2 C2_2 . 1.881(4) ?
O1_2 C5_2 . 1.230(4) ?
N1_2 C1_2 . 1.345(5) ?
N1_2 C4_2 . 1.385(4) ?
N1_2 H1_2 . 0.861(16) ?
C1_2 C2_2 . 1.380(5) ?
C1_2 H1A_2 . 0.95 ?
C2_2 C3_2 . 1.401(5) ?
C3_2 C4_2 . 1.406(5) ?
C3_2 C6_2 . 1.491(5) ?
C4_2 C5_2 . 1.431(5) ?
C5_2 H5_2 . 0.95 ?
C6_2 H6A_2 . 0.98 ?
C6_2 H6B_2 . 0.98 ?
C6_2 H6C_2 . 0.98 ?

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
C1_1 N1_1 C4_1 . . 109.6(3) ?
C1_1 N1_1 H1_1 . . 121.(3) ?
C4_1 N1_1 H1_1 . . 129.(3) ?
N1_1 C1_1 C2_1 . . 107.4(3) ?
N1_1 C1_1 H1A_1 . . 126.3 ?
C2_1 C1_1 H1A_1 . . 126.3 ?
C1_1 C2_1 C3_1 . . 109.3(3) ?
C1_1 C2_1 Br1_1 . . 126.2(3) ?
C3_1 C2_1 Br1_1 . . 124.5(3) ?
C4_1 C3_1 C2_1 . . 105.4(3) ?
C4_1 C3_1 C6_1 . . 128.1(3) ?
C2_1 C3_1 C6_1 . . 126.5(3) ?
N1_1 C4_1 C3_1 . . 108.3(3) ?
N1_1 C4_1 C5_1 . . 123.5(3) ?
C3_1 C4_1 C5_1 . . 128.2(3) ?
O1_1 C5_1 C4_1 . . 126.5(3) ?
O1_1 C5_1 H5_1 . . 116.7 ?
C4_1 C5_1 H5_1 . . 116.7 ?
C3_1 C6_1 H6A_1 . . 109.5 ?
C3_1 C6_1 H6B_1 . . 109.5 ?
H6A_1 C6_1 H6B_1 . . 109.5 ?
C3_1 C6_1 H6C_1 . . 109.5 ?
H6A_1 C6_1 H6C_1 . . 109.5 ?
H6B_1 C6_1 H6C_1 . . 109.5 ?
C1_2 N1_2 C4_2 . . 109.7(3) ?
C1_2 N1_2 H1_2 . . 131.(3) ?
C4_2 N1_2 H1_2 . . 119.(3) ?
N1_2 C1_2 C2_2 . . 107.6(3) ?
N1_2 C1_2 H1A_2 . . 126.2 ?
C2_2 C1_2 H1A_2 . . 126.2 ?
C1_2 C2_2 C3_2 . . 109.6(3) ?
C1_2 C2_2 Br1_2 . . 125.8(3) ?
C3_2 C2_2 Br1_2 . . 124.5(3) ?
C2_2 C3_2 C4_2 . . 105.1(3) ?
C2_2 C3_2 C6_2 . . 126.9(3) ?
C4_2 C3_2 C6_2 . . 128.0(3) ?
N1_2 C4_2 C3_2 . . 107.9(3) ?
N1_2 C4_2 C5_2 . . 123.2(3) ?
C3_2 C4_2 C5_2 . . 128.8(3) ?
O1_2 C5_2 C4_2 . . 125.6(3) ?
O1_2 C5_2 H5_2 . . 117.2 ?
C4_2 C5_2 H5_2 . . 117.2 ?
C3_2 C6_2 H6A_2 . . 109.5 ?
C3_2 C6_2 H6B_2 . . 109.5 ?
H6A_2 C6_2 H6B_2 . . 109.5 ?
C3_2 C6_2 H6C_2 . . 109.5 ?
H6A_2 C6_2 H6C_2 . . 109.5 ?
H6B_2 C6_2 H6C_2 . . 109.5 ?

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
C4_1 N1_1 C1_1 C2_1 . . . . 0.9(4) ?
N1_1 C1_1 C2_1 C3_1 . . . . -0.9(4) ?
N1_1 C1_1 C2_1 Br1_1 . . . . 178.1(2) ?
C1_1 C2_1 C3_1 C4_1 . . . . 0.5(4) ?
Br1_1 C2_1 C3_1 C4_1 . . . . -178.5(2) ?
C1_1 C2_1 C3_1 C6_1 . . . . -179.5(3) ?
Br1_1 C2_1 C3_1 C6_1 . . . . 1.6(5) ?
C1_1 N1_1 C4_1 C3_1 . . . . -0.6(4) ?
C1_1 N1_1 C4_1 C5_1 . . . . -179.3(3) ?
C2_1 C3_1 C4_1 N1_1 . . . . 0.0(4) ?
C6_1 C3_1 C4_1 N1_1 . . . . 180.0(3) ?
C2_1 C3_1 C4_1 C5_1 . . . . 178.7(3) ?
C6_1 C3_1 C4_1 C5_1 . . . . -1.3(6) ?
N1_1 C4_1 C5_1 O1_1 . . . . 0.5(6) ?
C3_1 C4_1 C5_1 O1_1 . . . . -178.0(3) ?
C4_2 N1_2 C1_2 C2_2 . . . . -0.6(4) ?
N1_2 C1_2 C2_2 C3_2 . . . . 0.4(4) ?
N1_2 C1_2 C2_2 Br1_2 . . . . 180.0(2) ?
C1_2 C2_2 C3_2 C4_2 . . . . 0.0(4) ?
Br1_2 C2_2 C3_2 C4_2 . . . . -179.6(2) ?
C1_2 C2_2 C3_2 C6_2 . . . . 179.5(3) ?
Br1_2 C2_2 C3_2 C6_2 . . . . -0.1(5) ?
C1_2 N1_2 C4_2 C3_2 . . . . 0.5(4) ?
C1_2 N1_2 C4_2 C5_2 . . . . 177.7(3) ?
C2_2 C3_2 C4_2 N1_2 . . . . -0.3(4) ?
C6_2 C3_2 C4_2 N1_2 . . . . -179.8(3) ?
C2_2 C3_2 C4_2 C5_2 . . . . -177.2(3) ?
C6_2 C3_2 C4_2 C5_2 . . . . 3.2(6) ?
N1_2 C4_2 C5_2 O1_2 . . . . -1.2(6) ?
C3_2 C4_2 C5_2 O1_2 . . . . 175.3(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1_1 H1_1 O1_2 . 0.858(16) 1.972(19) 2.817(4) 168.(4) ?
N1_2 H1_2 O1_1 . 0.861(16) 2.00(3) 2.797(4) 153.(4) ?

####################################################################### 
# 
# 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_rs052
_database_code_depnum_ccdc_archive 'CCDC 2083661'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;Molecular Education, Technology, and Research Innovation Center, North Carolina State University
United States of America
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            DC-006
_chemical_formula_moiety         'C26 H34 N2 O10 S'
_chemical_formula_sum            'C26 H34 N2 O10 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         566.61

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   29.6209(10)
_cell_length_b                   12.7399(4)
_cell_length_c                   16.3799(6)
_cell_angle_alpha                90
_cell_angle_beta                 116.8250(10)
_cell_angle_gamma                90
_cell_volume                     5516.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    809
_cell_measurement_theta_min      2.0473
_cell_measurement_theta_max      21.7238
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.161
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2400

_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

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

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            98657
_diffrn_reflns_av_R_equivalents  0.0560
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         32.04
_diffrn_reflns_theta_full        32.04
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
;

_reflns_number_total             9585
_reflns_number_gt                7757
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.1026
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_number_reflns         9585
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+4.6318P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.380
_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 Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

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
S S1 0.26738(2) 0.58474(2) 0.51809(2) 0.01552(6) Uani d . . . 1 . .
O O1 0.43587(3) 0.81590(8) 0.47548(6) 0.02729(19) Uani d . . . 1 . .
O O2 0.51633(3) 0.89428(8) 0.66929(6) 0.0284(2) Uani d . . . 1 . .
O O3 0.45916(3) 1.01961(7) 0.59494(6) 0.02333(17) Uani d . . . 1 . .
O O4 0.21558(4) 0.82282(7) 0.21141(6) 0.02789(19) Uani d . . . 1 . .
O O5 0.25074(4) 0.70606(8) 0.16302(7) 0.0302(2) Uani d . . . 1 . .
O O6 0.12160(3) 0.75104(7) 0.25819(5) 0.02098(16) Uani d . . . 1 . .
O O7 0.04826(3) 0.88276(8) 0.16671(6) 0.02726(19) Uani d . . . 1 . .
O O8 0.06361(3) 0.85477(7) 0.03971(6) 0.02355(17) Uani d . . . 1 . .
O O9 0.27031(3) 0.64527(7) 0.59350(6) 0.02006(16) Uani d . . . 1 . .
O O10 0.21965(3) 0.55300(7) 0.44667(6) 0.02189(17) Uani d . . . 1 . .
N N1 0.29631(3) 0.65811(7) 0.46995(6) 0.01490(16) Uani d . . . 1 . .
N N2 0.22802(4) 0.73208(8) 0.20664(6) 0.01911(18) Uani d . . . 1 . .
C C1 0.33644(4) 0.72054(8) 0.52567(7) 0.01546(18) Uani d . . . 1 . .
H H1 0.343347 0.744785 0.585002 0.019 Uiso calc U . R 1 . .
C C2 0.36461(4) 0.74144(8) 0.48041(7) 0.01569(18) Uani d . . . 1 . .
C C3 0.34121(4) 0.68883(8) 0.39286(7) 0.01644(19) Uani d . . . 1 . .
C C4 0.29968(4) 0.63679(8) 0.38768(7) 0.01482(18) Uani d . . . 1 . .
C C5 0.25957(4) 0.57832(8) 0.30902(7) 0.01601(18) Uani d . . . 1 . .
H H5A 0.249323 0.515685 0.332375 0.019 Uiso calc U . R 1 . .
H H5B 0.273527 0.554011 0.267596 0.019 Uiso calc U . R 1 . .
C C6 0.21295(4) 0.64743(8) 0.25516(7) 0.01524(18) Uani d . . . 1 . .
H H6 0.203759 0.682725 0.300134 0.018 Uiso calc U . R 1 . .
C C7 0.16507(4) 0.58966(8) 0.18371(7) 0.01713(19) Uani d . . . 1 . .
C C8 0.12320(4) 0.66913(9) 0.12650(7) 0.0182(2) Uani d . . . 1 . .
H H8A 0.135901 0.711911 0.090767 0.022 Uiso calc U . R 1 . .
H H8B 0.093819 0.628753 0.08206 0.022 Uiso calc U . R 1 . .
C C9 0.10411(4) 0.74392(9) 0.17609(7) 0.01734(19) Uani d . . . 1 . .
C C10 0.05743(4) 0.80922(9) 0.11248(8) 0.0204(2) Uani d . . . 1 . .
H H10 0.027685 0.760822 0.085646 0.024 Uiso calc U . R 1 . .
C C11 0.41055(4) 0.80460(9) 0.51667(8) 0.0182(2) Uani d . . . 1 . .
C C12 0.42728(5) 0.85633(10) 0.60997(8) 0.0219(2) Uani d . . . 1 . .
H H12A 0.399612 0.90035 0.609443 0.026 Uiso calc U . R 1 . .
H H12B 0.435706 0.801939 0.657816 0.026 Uiso calc U . R 1 . .
C C13 0.47301(4) 0.92304(9) 0.63001(8) 0.0200(2) Uani d . . . 1 . .
C C14 0.50041(5) 1.08644(11) 0.60348(10) 0.0293(3) Uani d . . . 1 . .
H H14A 0.518388 1.053723 0.57242 0.044 Uiso calc U . R 1 . .
H H14B 0.523796 1.096228 0.668356 0.044 Uiso calc U . R 1 . .
H H14C 0.487061 1.154734 0.575447 0.044 Uiso calc U . R 1 . .
C C15 0.35899(5) 0.69317(10) 0.32076(8) 0.0230(2) Uani d . . . 1 . .
H H15A 0.354051 0.764209 0.295215 0.035 Uiso calc U . R 1 . .
H H15B 0.339584 0.643117 0.272006 0.035 Uiso calc U . R 1 . .
H H15C 0.394988 0.675013 0.347813 0.035 Uiso calc U . R 1 . .
C C16 0.14540(5) 0.51671(9) 0.23553(8) 0.0231(2) Uani d . . . 1 . .
H H16A 0.170345 0.461429 0.266383 0.035 Uiso calc U . R 1 . .
H H16B 0.113405 0.484809 0.192143 0.035 Uiso calc U . R 1 . .
H H16C 0.139924 0.557444 0.281034 0.035 Uiso calc U . R 1 . .
C C17 0.17634(5) 0.52269(10) 0.11692(8) 0.0255(2) Uani d . . . 1 . .
H H17A 0.189121 0.567883 0.083546 0.038 Uiso calc U . R 1 . .
H H17B 0.145238 0.487893 0.073424 0.038 Uiso calc U . R 1 . .
H H17C 0.201844 0.469621 0.151226 0.038 Uiso calc U . R 1 . .
C C18 -0.00009(6) 0.93159(13) 0.11972(11) 0.0364(3) Uani d . . . 1 . .
H H18A 0.000289 0.980167 0.073641 0.055 Uiso calc U . R 1 . .
H H18B -0.007777 0.970402 0.16359 0.055 Uiso calc U . R 1 . .
H H18C -0.025981 0.877751 0.089662 0.055 Uiso calc U . R 1 . .
C C19 0.10190(5) 0.93464(10) 0.06844(10) 0.0291(3) Uani d . . . 1 . .
H H19A 0.107546 0.956211 0.016348 0.044 Uiso calc U . R 1 . .
H H19B 0.133448 0.906902 0.117031 0.044 Uiso calc U . R 1 . .
H H19C 0.090834 0.995328 0.09155 0.044 Uiso calc U . R 1 . .
C C20 0.30787(4) 0.47624(9) 0.55847(7) 0.01756(19) Uani d . . . 1 . .
C C21 0.35508(4) 0.49069(10) 0.63339(8) 0.0214(2) Uani d . . . 1 . .
H H21 0.364443 0.55681 0.663191 0.026 Uiso calc U . R 1 . .
C C22 0.38801(5) 0.40591(11) 0.66323(9) 0.0272(3) Uani d . . . 1 . .
H H22 0.420647 0.414573 0.71319 0.033 Uiso calc U . R 1 . .
C C23 0.37380(6) 0.30790(11) 0.62076(9) 0.0310(3) Uani d . . . 1 . .
C C24 0.32662(6) 0.29644(10) 0.54696(9) 0.0290(3) Uani d . . . 1 . .
H H24 0.316833 0.229873 0.518142 0.035 Uiso calc U . R 1 . .
C C25 0.29327(5) 0.38023(9) 0.51417(8) 0.0228(2) Uani d . . . 1 . .
H H25 0.261195 0.372077 0.462605 0.027 Uiso calc U . R 1 . .
C C26 0.40892(8) 0.21515(14) 0.65636(13) 0.0494(5) Uani d . . . 1 . .
H H26A 0.444063 0.239361 0.681944 0.074 Uiso calc U . R 1 . .
H H26B 0.402237 0.166018 0.606152 0.074 Uiso calc U . R 1 . .
H H26C 0.403315 0.179774 0.704131 0.074 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
S1 O9 . 1.4252(8) ?
S1 O10 . 1.4276(9) ?
S1 N1 . 1.6852(9) ?
S1 C20 . 1.7524(11) ?
O1 C11 . 1.2226(14) ?
O2 C13 . 1.2039(14) ?
O3 C13 . 1.3413(15) ?
O3 C14 . 1.4433(14) ?
O4 N2 . 1.2264(13) ?
O5 N2 . 1.2278(13) ?
O6 C9 . 1.2066(13) ?
O7 C10 . 1.3994(14) ?
O7 C18 . 1.4267(16) ?
O8 C10 . 1.4099(14) ?
O8 C19 . 1.4357(16) ?
N1 C1 . 1.3782(14) ?
N1 C4 . 1.4215(13) ?
N2 C6 . 1.5213(14) ?
C1 C2 . 1.3693(15) ?
C1 H1 . 0.95 ?
C2 C3 . 1.4454(15) ?
C2 C11 . 1.4569(15) ?
C3 C4 . 1.3660(15) ?
C3 C15 . 1.4955(15) ?
C4 C5 . 1.4983(15) ?
C5 C6 . 1.5366(15) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.5572(15) ?
C6 H6 . 1.0 ?
C7 C17 . 1.5383(16) ?
C7 C16 . 1.5393(16) ?
C7 C8 . 1.5468(15) ?
C8 C9 . 1.5171(15) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.5459(16) ?
C10 H10 . 1.0 ?
C11 C12 . 1.5271(16) ?
C12 C13 . 1.5046(16) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 H15A . 0.98 ?
C15 H15B . 0.98 ?
C15 H15C . 0.98 ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 C25 . 1.3881(16) ?
C20 C21 . 1.3952(16) ?
C21 C22 . 1.3881(17) ?
C21 H21 . 0.95 ?
C22 C23 . 1.398(2) ?
C22 H22 . 0.95 ?
C23 C24 . 1.382(2) ?
C23 C26 . 1.5070(19) ?
C24 C25 . 1.3874(18) ?
C24 H24 . 0.95 ?
C25 H25 . 0.95 ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?

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
O9 S1 O10 . . 120.93(5) ?
O9 S1 N1 . . 105.10(5) ?
O10 S1 N1 . . 107.36(5) ?
O9 S1 C20 . . 109.64(5) ?
O10 S1 C20 . . 110.00(5) ?
N1 S1 C20 . . 102.01(5) ?
C13 O3 C14 . . 114.68(10) ?
C10 O7 C18 . . 112.62(10) ?
C10 O8 C19 . . 113.54(9) ?
C1 N1 C4 . . 109.24(8) ?
C1 N1 S1 . . 118.62(7) ?
C4 N1 S1 . . 127.27(7) ?
O4 N2 O5 . . 123.44(10) ?
O4 N2 C6 . . 117.87(9) ?
O5 N2 C6 . . 118.67(10) ?
C2 C1 N1 . . 107.94(9) ?
C2 C1 H1 . . 126.0 ?
N1 C1 H1 . . 126.0 ?
C1 C2 C3 . . 108.08(9) ?
C1 C2 C11 . . 124.89(10) ?
C3 C2 C11 . . 127.03(10) ?
C4 C3 C2 . . 107.57(9) ?
C4 C3 C15 . . 126.67(10) ?
C2 C3 C15 . . 125.74(10) ?
C3 C4 N1 . . 107.15(9) ?
C3 C4 C5 . . 129.56(10) ?
N1 C4 C5 . . 122.87(9) ?
C4 C5 C6 . . 111.54(9) ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5B . . 109.3 ?
C6 C5 H5B . . 109.3 ?
H5A C5 H5B . . 108.0 ?
N2 C6 C5 . . 107.85(8) ?
N2 C6 C7 . . 108.96(8) ?
C5 C6 C7 . . 116.01(9) ?
N2 C6 H6 . . 107.9 ?
C5 C6 H6 . . 107.9 ?
C7 C6 H6 . . 107.9 ?
C17 C7 C16 . . 108.36(10) ?
C17 C7 C8 . . 107.71(9) ?
C16 C7 C8 . . 109.25(9) ?
C17 C7 C6 . . 112.35(9) ?
C16 C7 C6 . . 108.30(9) ?
C8 C7 C6 . . 110.81(9) ?
C9 C8 C7 . . 118.51(9) ?
C9 C8 H8A . . 107.7 ?
C7 C8 H8A . . 107.7 ?
C9 C8 H8B . . 107.7 ?
C7 C8 H8B . . 107.7 ?
H8A C8 H8B . . 107.1 ?
O6 C9 C8 . . 124.58(10) ?
O6 C9 C10 . . 120.95(10) ?
C8 C9 C10 . . 114.41(9) ?
O7 C10 O8 . . 113.42(10) ?
O7 C10 C9 . . 107.65(9) ?
O8 C10 C9 . . 111.92(9) ?
O7 C10 H10 . . 107.9 ?
O8 C10 H10 . . 107.9 ?
C9 C10 H10 . . 107.9 ?
O1 C11 C2 . . 122.19(10) ?
O1 C11 C12 . . 119.91(10) ?
C2 C11 C12 . . 117.90(9) ?
C13 C12 C11 . . 108.41(9) ?
C13 C12 H12A . . 110.0 ?
C11 C12 H12A . . 110.0 ?
C13 C12 H12B . . 110.0 ?
C11 C12 H12B . . 110.0 ?
H12A C12 H12B . . 108.4 ?
O2 C13 O3 . . 123.67(11) ?
O2 C13 C12 . . 125.60(11) ?
O3 C13 C12 . . 110.70(10) ?
O3 C14 H14A . . 109.5 ?
O3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
O3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C3 C15 H15A . . 109.5 ?
C3 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C3 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
C7 C16 H16A . . 109.5 ?
C7 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C7 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C7 C17 H17A . . 109.5 ?
C7 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C7 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O7 C18 H18A . . 109.5 ?
O7 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
O7 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
O8 C19 H19A . . 109.5 ?
O8 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O8 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C25 C20 C21 . . 121.89(11) ?
C25 C20 S1 . . 119.94(9) ?
C21 C20 S1 . . 118.13(9) ?
C22 C21 C20 . . 118.24(12) ?
C22 C21 H21 . . 120.9 ?
C20 C21 H21 . . 120.9 ?
C21 C22 C23 . . 120.91(13) ?
C21 C22 H22 . . 119.5 ?
C23 C22 H22 . . 119.5 ?
C24 C23 C22 . . 119.20(12) ?
C24 C23 C26 . . 120.30(15) ?
C22 C23 C26 . . 120.48(15) ?
C23 C24 C25 . . 121.30(12) ?
C23 C24 H24 . . 119.4 ?
C25 C24 H24 . . 119.4 ?
C24 C25 C20 . . 118.43(12) ?
C24 C25 H25 . . 120.8 ?
C20 C25 H25 . . 120.8 ?
C23 C26 H26A . . 109.5 ?
C23 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C23 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?

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
O9 S1 N1 C1 . . . . 33.35(9) ?
O10 S1 N1 C1 . . . . 163.29(8) ?
C20 S1 N1 C1 . . . . -81.06(9) ?
O9 S1 N1 C4 . . . . -174.15(9) ?
O10 S1 N1 C4 . . . . -44.21(10) ?
C20 S1 N1 C4 . . . . 71.43(10) ?
C4 N1 C1 C2 . . . . 1.31(12) ?
S1 N1 C1 C2 . . . . 158.40(7) ?
N1 C1 C2 C3 . . . . -0.54(12) ?
N1 C1 C2 C11 . . . . -179.58(10) ?
C1 C2 C3 C4 . . . . -0.44(12) ?
C11 C2 C3 C4 . . . . 178.57(10) ?
C1 C2 C3 C15 . . . . 178.35(11) ?
C11 C2 C3 C15 . . . . -2.64(18) ?
C2 C3 C4 N1 . . . . 1.22(11) ?
C15 C3 C4 N1 . . . . -177.56(10) ?
C2 C3 C4 C5 . . . . 173.83(10) ?
C15 C3 C4 C5 . . . . -4.95(19) ?
C1 N1 C4 C3 . . . . -1.59(11) ?
S1 N1 C4 C3 . . . . -156.16(8) ?
C1 N1 C4 C5 . . . . -174.81(9) ?
S1 N1 C4 C5 . . . . 30.61(14) ?
C3 C4 C5 C6 . . . . -95.96(13) ?
N1 C4 C5 C6 . . . . 75.63(12) ?
O4 N2 C6 C5 . . . . -133.41(10) ?
O5 N2 C6 C5 . . . . 48.41(12) ?
O4 N2 C6 C7 . . . . 99.88(11) ?
O5 N2 C6 C7 . . . . -78.29(12) ?
C4 C5 C6 N2 . . . . 68.71(11) ?
C4 C5 C6 C7 . . . . -168.81(9) ?
N2 C6 C7 C17 . . . . 69.17(11) ?
C5 C6 C7 C17 . . . . -52.72(12) ?
N2 C6 C7 C16 . . . . -171.19(9) ?
C5 C6 C7 C16 . . . . 66.92(12) ?
N2 C6 C7 C8 . . . . -51.37(11) ?
C5 C6 C7 C8 . . . . -173.26(9) ?
C17 C7 C8 C9 . . . . 178.78(10) ?
C16 C7 C8 C9 . . . . 61.28(12) ?
C6 C7 C8 C9 . . . . -57.97(13) ?
C7 C8 C9 O6 . . . . 5.22(17) ?
C7 C8 C9 C10 . . . . -171.90(9) ?
C18 O7 C10 O8 . . . . 68.78(14) ?
C18 O7 C10 C9 . . . . -166.83(11) ?
C19 O8 C10 O7 . . . . 54.34(13) ?
C19 O8 C10 C9 . . . . -67.71(12) ?
O6 C9 C10 O7 . . . . 9.94(15) ?
C8 C9 C10 O7 . . . . -172.82(9) ?
O6 C9 C10 O8 . . . . 135.23(11) ?
C8 C9 C10 O8 . . . . -47.53(13) ?
C1 C2 C11 O1 . . . . 175.74(11) ?
C3 C2 C11 O1 . . . . -3.12(18) ?
C1 C2 C11 C12 . . . . -3.37(16) ?
C3 C2 C11 C12 . . . . 177.78(10) ?
O1 C11 C12 C13 . . . . 4.86(16) ?
C2 C11 C12 C13 . . . . -176.02(10) ?
C14 O3 C13 O2 . . . . 3.11(17) ?
C14 O3 C13 C12 . . . . -174.62(10) ?
C11 C12 C13 O2 . . . . -90.44(14) ?
C11 C12 C13 O3 . . . . 87.23(12) ?
O9 S1 C20 C25 . . . . 142.20(9) ?
O10 S1 C20 C25 . . . . 6.92(11) ?
N1 S1 C20 C25 . . . . -106.78(9) ?
O9 S1 C20 C21 . . . . -39.90(10) ?
O10 S1 C20 C21 . . . . -175.19(8) ?
N1 S1 C20 C21 . . . . 71.11(9) ?
C25 C20 C21 C22 . . . . 0.36(17) ?
S1 C20 C21 C22 . . . . -177.49(9) ?
C20 C21 C22 C23 . . . . -1.53(18) ?
C21 C22 C23 C24 . . . . 1.26(19) ?
C21 C22 C23 C26 . . . . -177.23(13) ?
C22 C23 C24 C25 . . . . 0.22(19) ?
C26 C23 C24 C25 . . . . 178.72(13) ?
C23 C24 C25 C20 . . . . -1.35(18) ?
C21 C20 C25 C24 . . . . 1.06(17) ?
S1 C20 C25 C24 . . . . 178.87(9) ?

####################################################################### 
# 
# 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_rs030
_database_code_depnum_ccdc_archive 'CCDC 2083659'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;Molecular Education, Technology, and Research Innovation Center, North Carolina State University
United States of America
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            DC-006
_chemical_formula_moiety         'C13 H12 Br N O3 S'
_chemical_formula_sum            'C13 H12 Br N O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         342.21

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3674(3)
_cell_length_b                   8.5936(3)
_cell_length_c                   10.4526(3)
_cell_angle_alpha                88.161(2)
_cell_angle_beta                 88.2410(10)
_cell_angle_gamma                63.805(2)
_cell_volume                     673.95(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    918
_cell_measurement_theta_min      2.6332
_cell_measurement_theta_max      23.6367
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.098
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344

_exptl_absorpt_coefficient_mu    3.207
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.64
_exptl_absorpt_correction_T_max  0.74

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

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

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            39430
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
The residual density near O1 appears to be part of a second orientation of 
pyrole ring, rotated 180 degrees. Refining an alternate position for Br 
suggests a 3% occupancy. Attempts to refine a second orientation of pyrole 
ring were not stable, and so were left out of the final structure.
;

_reflns_number_total             4118
_reflns_number_gt                3502
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0931
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         4118
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.6575P] 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         1.894
_refine_diff_density_min         -0.624
_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'
Br Br -0.2901 2.4595 '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 Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

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 0.35696(3) 0.54006(3) 0.34113(2) 0.03288(9) Uani d . . . 1 . .
S S1 0.27268(7) 0.12919(6) 0.72674(5) 0.01995(11) Uani d . . . 1 . .
O O1 -0.0906(2) 0.6867(2) 0.80818(19) 0.0364(4) Uani d . . . 1 . .
O O2 0.1170(2) 0.1446(2) 0.79588(17) 0.0275(3) Uani d . . . 1 . .
O O3 0.3639(2) -0.0119(2) 0.64267(17) 0.0282(3) Uani d . . . 1 . .
N N1 0.2094(2) 0.3082(2) 0.63074(16) 0.0193(3) Uani d . . . 1 . .
C C1 0.3076(3) 0.3040(3) 0.5208(2) 0.0214(4) Uani d . . . 1 . .
H H1 0.388402 0.203095 0.477573 0.026 Uiso calc U . R 1 . .
C C2 0.2669(3) 0.4711(3) 0.4861(2) 0.0227(4) Uani d . . . 1 . .
C C3 0.1453(3) 0.5855(3) 0.5764(2) 0.0220(4) Uani d . . . 1 . .
C C4 0.1124(3) 0.4822(3) 0.6675(2) 0.0203(4) Uani d . . . 1 . .
C C5 -0.0085(3) 0.5359(3) 0.7778(2) 0.0261(4) Uani d . . . 1 . .
H H5 -0.024014 0.449498 0.828344 0.031 Uiso calc U . R 1 . .
C C6 0.0711(4) 0.7788(3) 0.5702(3) 0.0324(5) Uani d . . . 1 . .
H H6A -0.042608 0.829916 0.617699 0.049 Uiso calc U . R 1 . .
H H6B 0.052063 0.818908 0.480663 0.049 Uiso calc U . R 1 . .
H H6C 0.155142 0.814361 0.608235 0.049 Uiso calc U . R 1 . .
C C7 0.4218(3) 0.1499(3) 0.8304(2) 0.0199(4) Uani d . . . 1 . .
C C8 0.5969(3) 0.0991(3) 0.7883(2) 0.0253(4) Uani d . . . 1 . .
H H8 0.637117 0.045376 0.707923 0.03 Uiso calc U . R 1 . .
C C9 0.7111(3) 0.1288(3) 0.8666(2) 0.0281(5) Uani d . . . 1 . .
H H9 0.831433 0.093607 0.839771 0.034 Uiso calc U . R 1 . .
C C10 0.6524(3) 0.2092(3) 0.9836(2) 0.0276(5) Uani d . . . 1 . .
C C11 0.4774(3) 0.2522(3) 1.0251(2) 0.0273(4) Uani d . . . 1 . .
H H11 0.437993 0.302226 1.106683 0.033 Uiso calc U . R 1 . .
C C12 0.3610(3) 0.2230(3) 0.9493(2) 0.0230(4) Uani d . . . 1 . .
H H12 0.242535 0.25221 0.97793 0.028 Uiso calc U . R 1 . .
C C13 0.7742(4) 0.2510(4) 1.0643(3) 0.0388(6) Uani d . . . 1 . .
H H13A 0.747376 0.240104 1.155115 0.058 Uiso calc U . R 1 . .
H H13B 0.756031 0.369979 1.044932 0.058 Uiso calc U . R 1 . .
H H13C 0.898319 0.170162 1.045215 0.058 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 C2 . 1.866(2) ?
S1 O2 . 1.4259(16) ?
S1 O3 . 1.4267(16) ?
S1 N1 . 1.6935(18) ?
S1 C7 . 1.748(2) ?
O1 C5 . 1.216(3) ?
N1 C1 . 1.383(3) ?
N1 C4 . 1.411(3) ?
C1 C2 . 1.361(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.418(3) ?
C3 C4 . 1.384(3) ?
C3 C6 . 1.495(3) ?
C4 C5 . 1.455(3) ?
C5 H5 . 0.95 ?
C6 H6A . 0.98 ?
C6 H6B . 0.98 ?
C6 H6C . 0.98 ?
C7 C12 . 1.388(3) ?
C7 C8 . 1.392(3) ?
C8 C9 . 1.388(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.391(4) ?
C9 H9 . 0.95 ?
C10 C11 . 1.400(3) ?
C10 C13 . 1.508(3) ?
C11 C12 . 1.384(3) ?
C11 H11 . 0.95 ?
C12 H12 . 0.95 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?

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
O2 S1 O3 . . 120.36(10) ?
O2 S1 N1 . . 106.55(9) ?
O3 S1 N1 . . 104.36(10) ?
O2 S1 C7 . . 110.09(10) ?
O3 S1 C7 . . 110.64(10) ?
N1 S1 C7 . . 103.20(9) ?
C1 N1 C4 . . 108.66(17) ?
C1 N1 S1 . . 119.87(15) ?
C4 N1 S1 . . 126.88(15) ?
C2 C1 N1 . . 107.37(19) ?
C2 C1 H1 . . 126.3 ?
N1 C1 H1 . . 126.3 ?
C1 C2 C3 . . 109.88(19) ?
C1 C2 Br1 . . 125.20(17) ?
C3 C2 Br1 . . 124.92(16) ?
C4 C3 C2 . . 106.31(18) ?
C4 C3 C6 . . 128.5(2) ?
C2 C3 C6 . . 125.2(2) ?
C3 C4 N1 . . 107.70(18) ?
C3 C4 C5 . . 128.4(2) ?
N1 C4 C5 . . 123.81(19) ?
O1 C5 C4 . . 122.8(2) ?
O1 C5 H5 . . 118.6 ?
C4 C5 H5 . . 118.6 ?
C3 C6 H6A . . 109.5 ?
C3 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C3 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C12 C7 C8 . . 122.1(2) ?
C12 C7 S1 . . 119.34(16) ?
C8 C7 S1 . . 118.53(17) ?
C9 C8 C7 . . 118.4(2) ?
C9 C8 H8 . . 120.8 ?
C7 C8 H8 . . 120.8 ?
C8 C9 C10 . . 121.0(2) ?
C8 C9 H9 . . 119.5 ?
C10 C9 H9 . . 119.5 ?
C9 C10 C11 . . 118.9(2) ?
C9 C10 C13 . . 120.7(2) ?
C11 C10 C13 . . 120.4(2) ?
C12 C11 C10 . . 121.2(2) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C7 . . 118.3(2) ?
C11 C12 H12 . . 120.8 ?
C7 C12 H12 . . 120.8 ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?

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
O2 S1 N1 C1 . . . . -155.99(16) ?
O3 S1 N1 C1 . . . . -27.65(18) ?
C7 S1 N1 C1 . . . . 88.06(17) ?
O2 S1 N1 C4 . . . . 50.88(19) ?
O3 S1 N1 C4 . . . . 179.22(17) ?
C7 S1 N1 C4 . . . . -65.07(18) ?
C4 N1 C1 C2 . . . . -2.7(2) ?
S1 N1 C1 C2 . . . . -160.30(15) ?
N1 C1 C2 C3 . . . . 1.8(2) ?
N1 C1 C2 Br1 . . . . -177.96(14) ?
C1 C2 C3 C4 . . . . -0.2(2) ?
Br1 C2 C3 C4 . . . . 179.57(15) ?
C1 C2 C3 C6 . . . . 179.8(2) ?
Br1 C2 C3 C6 . . . . -0.4(3) ?
C2 C3 C4 N1 . . . . -1.4(2) ?
C6 C3 C4 N1 . . . . 178.5(2) ?
C2 C3 C4 C5 . . . . -177.3(2) ?
C6 C3 C4 C5 . . . . 2.7(4) ?
C1 N1 C4 C3 . . . . 2.6(2) ?
S1 N1 C4 C3 . . . . 158.16(15) ?
C1 N1 C4 C5 . . . . 178.70(19) ?
S1 N1 C4 C5 . . . . -25.7(3) ?
C3 C4 C5 O1 . . . . -5.0(4) ?
N1 C4 C5 O1 . . . . 179.8(2) ?
O2 S1 C7 C12 . . . . -17.5(2) ?
O3 S1 C7 C12 . . . . -152.97(17) ?
N1 S1 C7 C12 . . . . 95.89(17) ?
O2 S1 C7 C8 . . . . 165.22(17) ?
O3 S1 C7 C8 . . . . 29.8(2) ?
N1 S1 C7 C8 . . . . -81.37(18) ?
C12 C7 C8 C9 . . . . -2.4(3) ?
S1 C7 C8 C9 . . . . 174.82(17) ?
C7 C8 C9 C10 . . . . -0.8(3) ?
C8 C9 C10 C11 . . . . 3.3(3) ?
C8 C9 C10 C13 . . . . -176.2(2) ?
C9 C10 C11 C12 . . . . -2.9(3) ?
C13 C10 C11 C12 . . . . 176.6(2) ?
C10 C11 C12 C7 . . . . -0.1(3) ?
C8 C7 C12 C11 . . . . 2.8(3) ?
S1 C7 C12 C11 . . . . -174.38(16) ?

####################################################################### 
# 
# 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_rs029
_database_code_depnum_ccdc_archive 'CCDC 2083660'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;Molecular Education, Technology, and Research Innovation Center, North Carolina State University
United States of America
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            VP-003
_chemical_formula_moiety         'C7 H8 I N O'
_chemical_formula_sum            'C7 H8 I N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         249.04

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.8097(5)
_cell_length_b                   12.6229(8)
_cell_length_c                   14.4382(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1605.59(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4497
_cell_measurement_theta_min      2.8113
_cell_measurement_theta_max      29.0301
_cell_measurement_temperature    108.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.111
_exptl_crystal_size_mid          0.104
_exptl_crystal_size_min          0.089
_exptl_crystal_density_diffrn    2.061
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944

_exptl_absorpt_coefficient_mu    3.920
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.72

_exptl_special_details           
;
;

_diffrn_ambient_temperature      108.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

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

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            67230
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_theta_min         2.82
_diffrn_reflns_theta_max         33.11
_diffrn_reflns_theta_full        33.11
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             3062
_reflns_number_gt                2497
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0198
_refine_ls_wR_factor_gt          0.0388
_refine_ls_wR_factor_ref         0.0415
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_number_reflns         3062
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²+1.3684P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.716
_refine_diff_density_min         -0.850
_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'
I I -0.4742 1.8119 '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'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

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
I I1 0.28709(2) 0.45486(2) 0.48143(2) 0.01497(3) Uani d . . . 1 . .
O O1 0.11357(14) 0.30315(10) 0.09616(8) 0.0165(2) Uani d . . . 1 . .
N N1 0.10269(16) 0.26938(11) 0.41117(9) 0.0124(3) Uani d . . . 1 . .
H H1 0.092(2) 0.2504(17) 0.4689(14) 0.015 Uiso d U . . 1 . .
C C1 0.18723(17) 0.35634(12) 0.38431(10) 0.0114(3) Uani d . . . 1 . .
C C2 0.18730(17) 0.36468(12) 0.28964(10) 0.0105(3) Uani d . . . 1 . .
C C3 0.09667(18) 0.27729(12) 0.25689(11) 0.0110(3) Uani d . . . 1 . .
C C4 0.04733(18) 0.22123(13) 0.33440(11) 0.0127(3) Uani d . . . 1 . .
H H4 -0.014654 0.159649 0.333549 0.015 Uiso calc U . R 1 . .
C C5 0.2650(2) 0.44711(13) 0.23273(11) 0.0163(3) Uani d . . . 1 . .
H H5A 0.334893 0.412848 0.18924 0.025 Uiso calc U . R 1 . .
H H5B 0.322028 0.494809 0.273438 0.025 Uiso calc U . R 1 . .
H H5C 0.189119 0.48781 0.198129 0.025 Uiso calc U . R 1 . .
C C6 0.06078(18) 0.25133(12) 0.16116(10) 0.0116(3) Uani d . . . 1 . .
C C7 -0.04270(19) 0.15848(13) 0.14287(11) 0.0154(3) Uani d . . . 1 . .
H H7A -0.070982 0.157447 0.077229 0.023 Uiso calc U . R 1 . .
H H7B -0.13436 0.165141 0.180886 0.023 Uiso calc U . R 1 . .
H H7C 0.009994 0.092519 0.158606 0.023 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
I1 C1 . 2.0704(15) ?
O1 C6 . 1.2348(19) ?
N1 C4 . 1.355(2) ?
N1 C1 . 1.382(2) ?
N1 H1 . 0.87(2) ?
C1 C2 . 1.371(2) ?
C2 C3 . 1.442(2) ?
C2 C5 . 1.492(2) ?
C3 C4 . 1.394(2) ?
C3 C6 . 1.455(2) ?
C4 H4 . 0.95 ?
C5 H5A . 0.98 ?
C5 H5B . 0.98 ?
C5 H5C . 0.98 ?
C6 C7 . 1.508(2) ?
C7 H7A . 0.98 ?
C7 H7B . 0.98 ?
C7 H7C . 0.98 ?

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
C4 N1 C1 . . 108.71(13) ?
C4 N1 H1 . . 128.2(14) ?
C1 N1 H1 . . 123.1(14) ?
C2 C1 N1 . . 109.94(13) ?
C2 C1 I1 . . 128.97(12) ?
N1 C1 I1 . . 121.07(11) ?
C1 C2 C3 . . 105.55(13) ?
C1 C2 C5 . . 127.07(14) ?
C3 C2 C5 . . 127.38(14) ?
C4 C3 C2 . . 107.33(14) ?
C4 C3 C6 . . 125.49(14) ?
C2 C3 C6 . . 127.17(14) ?
N1 C4 C3 . . 108.47(14) ?
N1 C4 H4 . . 125.8 ?
C3 C4 H4 . . 125.8 ?
C2 C5 H5A . . 109.5 ?
C2 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
C2 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
O1 C6 C3 . . 121.38(15) ?
O1 C6 C7 . . 120.42(14) ?
C3 C6 C7 . . 118.20(13) ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?

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
C4 N1 C1 C2 . . . . -0.17(18) ?
C4 N1 C1 I1 . . . . 178.18(11) ?
N1 C1 C2 C3 . . . . 0.13(18) ?
I1 C1 C2 C3 . . . . -178.05(11) ?
N1 C1 C2 C5 . . . . -179.89(15) ?
I1 C1 C2 C5 . . . . 1.9(2) ?
C1 C2 C3 C4 . . . . -0.05(17) ?
C5 C2 C3 C4 . . . . 179.98(15) ?
C1 C2 C3 C6 . . . . 179.49(15) ?
C5 C2 C3 C6 . . . . -0.5(3) ?
C1 N1 C4 C3 . . . . 0.14(18) ?
C2 C3 C4 N1 . . . . -0.06(18) ?
C6 C3 C4 N1 . . . . -179.61(15) ?
C4 C3 C6 O1 . . . . -177.46(16) ?
C2 C3 C6 O1 . . . . 3.1(3) ?
C4 C3 C6 C7 . . . . 2.2(2) ?
C2 C3 C6 C7 . . . . -177.23(15) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 7_566 0.87(2) 1.97(2) 2.8251(17) 167.(2) ?

####################################################################### 
# 
# 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_rs056
_database_code_depnum_ccdc_archive 'CCDC 2083662'
loop_
_audit_author_name
_audit_author_address
'Roger D. Sommer'
;Molecular Education, Technology, and Research Innovation Center, North Carolina State University
United States of America
;
_audit_update_record             
;
2021-05-13 deposited with the CCDC.	2021-06-29 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            DC-005
_chemical_formula_moiety         '(C22 H29 Br N2 O7 S), 0.5(H2 O)'

_chemical_formula_sum            'C22 H30 Br N2 O7.50 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         554.45

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   36.3995(13)
_cell_length_b                   6.3576(2)
_cell_length_c                   25.0600(9)
_cell_angle_alpha                90
_cell_angle_beta                 123.6400(10)
_cell_angle_gamma                90
_cell_volume                     4828.1(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9824
_cell_measurement_theta_min      2.9164
_cell_measurement_theta_max      79.1267
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.057
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2296

_exptl_absorpt_coefficient_mu    3.545
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
(Bruker AXS Inc., 2016)
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.82

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'Incoatec I\mS 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'multilayer mirror'

_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            49434
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         79.59
_diffrn_reflns_theta_full        79.59
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31

_refine_special_details          
;
;

_reflns_number_total             5163
_reflns_number_gt                5105
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0610
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_number_reflns         5163
_refine_ls_number_parameters     313
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+5.7125P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.295
_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 0.0181 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'
Br Br -0.6763 1.2805 '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'
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'

_computing_data_collection       
'Bruker Instrument Service, BIS, v.6.2.10 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.40A (Bruker AXS Inc., 2018)'
_computing_structure_solution    'XT, VERSION 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, 2019)'
_computing_publication_material  ?

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 0.71717(2) 0.93030(2) 0.77913(2) 0.02373(6) Uani d . . . 1 . .
S S1 0.68608(2) 0.90298(5) 0.53858(2) 0.01454(7) Uani d . . . 1 . .
O O1 0.56936(3) 0.50380(17) 0.57477(5) 0.0251(2) Uani d . . . 1 . .
O O2 0.53120(3) 0.73260(16) 0.49995(5) 0.0251(2) Uani d . . . 1 . .
O O3 0.53267(3) 0.76848(16) 0.36156(5) 0.0231(2) Uani d . . . 1 . .
O O4 0.45618(3) 0.95618(16) 0.32087(5) 0.0239(2) Uani d . . . 1 . .
O O5 0.42829(3) 0.61572(16) 0.28691(5) 0.0227(2) Uani d . . . 1 . .
O O6 0.69378(3) 1.12459(15) 0.54196(5) 0.02054(19) Uani d . . . 1 . .
O O7 0.65211(3) 0.80690(16) 0.48024(4) 0.01977(19) Uani d . . . 1 . .
N N2 0.67373(3) 0.85667(17) 0.59297(5) 0.0147(2) Uani d . . . 1 . .
N N3 0.56093(3) 0.60200(17) 0.52722(5) 0.0168(2) Uani d . . . 1 . .
C C1 0.69612(4) 0.9693(2) 0.65073(6) 0.0170(2) Uani d . . . 1 . .
H H1 0.709895 1.102721 0.658014 0.02 Uiso calc U . R 1 . .
C C2 0.69428(4) 0.8515(2) 0.69395(6) 0.0172(2) Uani d . . . 1 . .
C C3 0.67150(4) 0.6581(2) 0.66555(6) 0.0157(2) Uani d . . . 1 . .
C C4 0.65952(4) 0.66187(19) 0.60318(6) 0.0141(2) Uani d . . . 1 . .
C C5 0.63486(4) 0.4984(2) 0.55247(6) 0.0147(2) Uani d . . . 1 . .
H H5A 0.633758 0.368003 0.573126 0.018 Uiso calc U . R 1 . .
H H5B 0.65164 0.466562 0.533049 0.018 Uiso calc U . R 1 . .
C C6 0.58758(4) 0.55842(19) 0.49872(6) 0.0141(2) Uani d . . . 1 . .
H H6 0.588797 0.690505 0.478077 0.017 Uiso calc U . R 1 . .
C C7 0.56333(4) 0.3870(2) 0.44578(6) 0.0172(2) Uani d . . . 1 . .
C C8 0.51503(4) 0.4506(2) 0.39575(6) 0.0184(2) Uani d . . . 1 . .
H H8A 0.502332 0.345631 0.360718 0.022 Uiso calc U . R 1 . .
H H8B 0.498482 0.439438 0.416384 0.022 Uiso calc U . R 1 . .
C C9 0.50644(4) 0.6664(2) 0.36584(6) 0.0177(2) Uani d . . . 1 . .
C C10 0.45914(4) 0.7461(2) 0.33833(6) 0.0189(2) Uani d . . . 1 . .
H H10 0.45334 0.736782 0.372877 0.023 Uiso calc U . R 1 . .
C C11 0.66386(5) 0.4885(2) 0.69984(6) 0.0215(3) Uani d . . . 1 . .
H H11A 0.692143 0.446151 0.738226 0.032 Uiso calc U . R 1 . .
H H11B 0.650075 0.367022 0.671403 0.032 Uiso calc U . R 1 . .
H H11C 0.64438 0.541463 0.712342 0.032 Uiso calc U . R 1 . .
C C12 0.56164(5) 0.1744(2) 0.47344(7) 0.0244(3) Uani d . . . 1 . .
H H12A 0.591747 0.125134 0.50454 0.037 Uiso calc U . R 1 . .
H H12B 0.546131 0.071535 0.438673 0.037 Uiso calc U . R 1 . .
H H12C 0.545946 0.190846 0.494755 0.037 Uiso calc U . R 1 . .
C C13 0.58852(4) 0.3613(2) 0.41321(7) 0.0236(3) Uani d . . . 1 . .
H H13A 0.593601 0.50005 0.401375 0.035 Uiso calc U . R 1 . .
H H13B 0.571099 0.274901 0.374605 0.035 Uiso calc U . R 1 . .
H H13C 0.616933 0.292768 0.442881 0.035 Uiso calc U . R 1 . .
C C14 0.73613(4) 0.7716(2) 0.56799(6) 0.0152(2) Uani d . . . 1 . .
C C15 0.73567(5) 0.5723(2) 0.54470(7) 0.0187(3) Uani d . . . 1 . .
H H15 0.708696 0.508674 0.512394 0.022 Uiso calc U . R 1 . .
C C16 0.77560(5) 0.4685(2) 0.56977(7) 0.0216(3) Uani d . . . 1 . .
H H16 0.775728 0.332449 0.554203 0.026 Uiso calc U . R 1 . .
C C17 0.81535(5) 0.5592(2) 0.61712(7) 0.0226(3) Uani d . . . 1 . .
C C18 0.81477(4) 0.7596(2) 0.63931(6) 0.0227(3) Uani d . . . 1 . .
H H18 0.841762 0.823392 0.671504 0.027 Uiso calc U . R 1 . .
C C19 0.77543(4) 0.8674(2) 0.61516(6) 0.0187(2) Uani d . . . 1 . .
H H19 0.775302 1.003922 0.630495 0.022 Uiso calc U . R 1 . .
C C20 0.85821(5) 0.4430(3) 0.64445(8) 0.0351(4) Uani d . . . 1 . .
H H20A 0.852118 0.294645 0.631922 0.053 Uiso calc U . R 1 . .
H H20B 0.875737 0.453918 0.691296 0.053 Uiso calc U . R 1 . .
H H20C 0.874672 0.504827 0.627912 0.053 Uiso calc U . R 1 . .
C C21 0.42259(5) 1.0655(2) 0.32305(8) 0.0304(3) Uani d . . . 1 . .
H H21A 0.394309 0.992883 0.29576 0.046 Uiso calc U . R 1 . .
H H21B 0.420082 1.209771 0.307599 0.046 Uiso calc U . R 1 . .
H H21C 0.430407 1.068571 0.367278 0.046 Uiso calc U . R 1 . .
C C22 0.43634(5) 0.5932(3) 0.23735(7) 0.0303(3) Uani d . . . 1 . .
H H22A 0.410948 0.524654 0.20007 0.045 Uiso calc U . R 1 . .
H H22B 0.462794 0.507335 0.253113 0.045 Uiso calc U . R 1 . .
H H22C 0.440765 0.732384 0.224957 0.045 Uiso calc U . R 1 . .
O O1S 0.5 1.1315(3) 0.25 0.0480(5) Uani d T P S 1 . .
H H1S 0.4952(11) 1.029(5) 0.2742(15) 0.091(10) Uiso d . . . 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 C2 . 1.8791(12) ?
S1 O7 . 1.4270(10) ?
S1 O6 . 1.4298(10) ?
S1 N2 . 1.6808(10) ?
S1 C14 . 1.7529(12) ?
O1 N3 . 1.2242(15) ?
O2 N3 . 1.2280(15) ?
O3 C9 . 1.2076(17) ?
O4 C10 . 1.3913(16) ?
O4 C21 . 1.4336(18) ?
O5 C10 . 1.4159(16) ?
O5 C22 . 1.4322(18) ?
N2 C1 . 1.4020(16) ?
N2 C4 . 1.4190(16) ?
N3 C6 . 1.5153(15) ?
C1 C2 . 1.3489(19) ?
C1 H1 . 0.95 ?
C2 C3 . 1.4322(18) ?
C3 C4 . 1.3706(17) ?
C3 C11 . 1.4975(18) ?
C4 C5 . 1.4956(17) ?
C5 C6 . 1.5340(16) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.5588(17) ?
C6 H6 . 1.0 ?
C7 C12 . 1.5356(19) ?
C7 C13 . 1.5373(18) ?
C7 C8 . 1.5442(17) ?
C8 C9 . 1.5105(18) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.5429(17) ?
C10 H10 . 1.0 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 C15 . 1.3912(18) ?
C14 C19 . 1.3935(18) ?
C15 C16 . 1.3893(19) ?
C15 H15 . 0.95 ?
C16 C17 . 1.390(2) ?
C16 H16 . 0.95 ?
C17 C18 . 1.395(2) ?
C17 C20 . 1.5050(19) ?
C18 C19 . 1.3879(18) ?
C18 H18 . 0.95 ?
C19 H19 . 0.95 ?
C20 H20A . 0.98 ?
C20 H20B . 0.98 ?
C20 H20C . 0.98 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
O1S H1S . 0.97(3) ?

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
O7 S1 O6 . . 120.85(6) ?
O7 S1 N2 . . 106.66(5) ?
O6 S1 N2 . . 104.84(6) ?
O7 S1 C14 . . 109.61(6) ?
O6 S1 C14 . . 108.71(6) ?
N2 S1 C14 . . 104.95(5) ?
C10 O4 C21 . . 111.88(11) ?
C10 O5 C22 . . 114.06(11) ?
C1 N2 C4 . . 108.73(10) ?
C1 N2 S1 . . 118.96(8) ?
C4 N2 S1 . . 125.95(8) ?
O1 N3 O2 . . 123.70(11) ?
O1 N3 C6 . . 119.01(10) ?
O2 N3 C6 . . 117.27(10) ?
C2 C1 N2 . . 106.63(11) ?
C2 C1 H1 . . 126.7 ?
N2 C1 H1 . . 126.7 ?
C1 C2 C3 . . 110.51(11) ?
C1 C2 Br1 . . 125.17(10) ?
C3 C2 Br1 . . 124.31(10) ?
C4 C3 C2 . . 106.41(11) ?
C4 C3 C11 . . 128.61(12) ?
C2 C3 C11 . . 124.97(11) ?
C3 C4 N2 . . 107.67(11) ?
C3 C4 C5 . . 128.24(11) ?
N2 C4 C5 . . 124.07(11) ?
C4 C5 C6 . . 115.25(10) ?
C4 C5 H5A . . 108.5 ?
C6 C5 H5A . . 108.5 ?
C4 C5 H5B . . 108.5 ?
C6 C5 H5B . . 108.5 ?
H5A C5 H5B . . 107.5 ?
N3 C6 C5 . . 109.35(10) ?
N3 C6 C7 . . 108.68(9) ?
C5 C6 C7 . . 113.85(10) ?
N3 C6 H6 . . 108.3 ?
C5 C6 H6 . . 108.3 ?
C7 C6 H6 . . 108.3 ?
C12 C7 C13 . . 109.35(11) ?
C12 C7 C8 . . 106.54(10) ?
C13 C7 C8 . . 110.03(11) ?
C12 C7 C6 . . 112.13(11) ?
C13 C7 C6 . . 107.62(10) ?
C8 C7 C6 . . 111.17(10) ?
C9 C8 C7 . . 118.06(11) ?
C9 C8 H8A . . 107.8 ?
C7 C8 H8A . . 107.8 ?
C9 C8 H8B . . 107.8 ?
C7 C8 H8B . . 107.8 ?
H8A C8 H8B . . 107.1 ?
O3 C9 C8 . . 125.15(12) ?
O3 C9 C10 . . 121.68(12) ?
C8 C9 C10 . . 113.14(11) ?
O4 C10 O5 . . 113.05(11) ?
O4 C10 C9 . . 109.19(11) ?
O5 C10 C9 . . 109.91(10) ?
O4 C10 H10 . . 108.2 ?
O5 C10 H10 . . 108.2 ?
C9 C10 H10 . . 108.2 ?
C3 C11 H11A . . 109.5 ?
C3 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C3 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C7 C12 H12A . . 109.5 ?
C7 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C7 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C7 C13 H13A . . 109.5 ?
C7 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C7 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C15 C14 C19 . . 121.48(12) ?
C15 C14 S1 . . 119.32(10) ?
C19 C14 S1 . . 119.19(10) ?
C16 C15 C14 . . 118.45(13) ?
C16 C15 H15 . . 120.8 ?
C14 C15 H15 . . 120.8 ?
C15 C16 C17 . . 121.49(13) ?
C15 C16 H16 . . 119.3 ?
C17 C16 H16 . . 119.3 ?
C16 C17 C18 . . 118.74(12) ?
C16 C17 C20 . . 120.74(14) ?
C18 C17 C20 . . 120.51(14) ?
C19 C18 C17 . . 121.14(13) ?
C19 C18 H18 . . 119.4 ?
C17 C18 H18 . . 119.4 ?
C18 C19 C14 . . 118.69(13) ?
C18 C19 H19 . . 120.7 ?
C14 C19 H19 . . 120.7 ?
C17 C20 H20A . . 109.5 ?
C17 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C17 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
O4 C21 H21A . . 109.5 ?
O4 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
O4 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
O5 C22 H22A . . 109.5 ?
O5 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
O5 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?

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
O7 S1 N2 C1 . . . . -166.71(9) ?
O6 S1 N2 C1 . . . . -37.45(11) ?
C14 S1 N2 C1 . . . . 77.03(10) ?
O7 S1 N2 C4 . . . . 44.55(11) ?
O6 S1 N2 C4 . . . . 173.82(10) ?
C14 S1 N2 C4 . . . . -71.70(11) ?
C4 N2 C1 C2 . . . . -2.09(13) ?
S1 N2 C1 C2 . . . . -155.75(9) ?
N2 C1 C2 C3 . . . . 1.20(14) ?
N2 C1 C2 Br1 . . . . -177.57(8) ?
C1 C2 C3 C4 . . . . 0.15(14) ?
Br1 C2 C3 C4 . . . . 178.94(9) ?
C1 C2 C3 C11 . . . . 179.17(12) ?
Br1 C2 C3 C11 . . . . -2.04(18) ?
C2 C3 C4 N2 . . . . -1.43(13) ?
C11 C3 C4 N2 . . . . 179.59(12) ?
C2 C3 C4 C5 . . . . -179.81(11) ?
C11 C3 C4 C5 . . . . 1.2(2) ?
C1 N2 C4 C3 . . . . 2.21(13) ?
S1 N2 C4 C3 . . . . 153.56(9) ?
C1 N2 C4 C5 . . . . -179.33(11) ?
S1 N2 C4 C5 . . . . -27.98(16) ?
C3 C4 C5 C6 . . . . 109.32(14) ?
N2 C4 C5 C6 . . . . -68.82(15) ?
O1 N3 C6 C5 . . . . -32.43(15) ?
O2 N3 C6 C5 . . . . 149.02(11) ?
O1 N3 C6 C7 . . . . 92.41(13) ?
O2 N3 C6 C7 . . . . -86.14(13) ?
C4 C5 C6 N3 . . . . -59.79(13) ?
C4 C5 C6 C7 . . . . 178.44(10) ?
N3 C6 C7 C12 . . . . -65.14(13) ?
C5 C6 C7 C12 . . . . 56.99(14) ?
N3 C6 C7 C13 . . . . 174.56(10) ?
C5 C6 C7 C13 . . . . -63.31(13) ?
N3 C6 C7 C8 . . . . 54.00(13) ?
C5 C6 C7 C8 . . . . 176.14(10) ?
C12 C7 C8 C9 . . . . 173.36(11) ?
C13 C7 C8 C9 . . . . -68.20(15) ?
C6 C7 C8 C9 . . . . 50.92(15) ?
C7 C8 C9 O3 . . . . 24.11(19) ?
C7 C8 C9 C10 . . . . -157.68(11) ?
C21 O4 C10 O5 . . . . 83.92(14) ?
C21 O4 C10 C9 . . . . -153.41(11) ?
C22 O5 C10 O4 . . . . 67.68(14) ?
C22 O5 C10 C9 . . . . -54.59(15) ?
O3 C9 C10 O4 . . . . -10.78(17) ?
C8 C9 C10 O4 . . . . 170.94(10) ?
O3 C9 C10 O5 . . . . 113.75(14) ?
C8 C9 C10 O5 . . . . -64.53(14) ?
O7 S1 C14 C15 . . . . -16.83(12) ?
O6 S1 C14 C15 . . . . -150.88(10) ?
N2 S1 C14 C15 . . . . 97.38(10) ?
O7 S1 C14 C19 . . . . 164.46(10) ?
O6 S1 C14 C19 . . . . 30.40(12) ?
N2 S1 C14 C19 . . . . -81.34(11) ?
C19 C14 C15 C16 . . . . 0.28(19) ?
S1 C14 C15 C16 . . . . -178.41(10) ?
C14 C15 C16 C17 . . . . 0.1(2) ?
C15 C16 C17 C18 . . . . -0.4(2) ?
C15 C16 C17 C20 . . . . 179.03(13) ?
C16 C17 C18 C19 . . . . 0.3(2) ?
C20 C17 C18 C19 . . . . -179.11(13) ?
C17 C18 C19 C14 . . . . 0.1(2) ?
C15 C14 C19 C18 . . . . -0.35(19) ?
S1 C14 C19 C18 . . . . 178.33(10) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1S H1S O3 . 0.97(3) 2.47(3) 3.2972(17) 143.(3) ?
O1S H1S O4 . 0.97(3) 2.33(3) 3.1746(12) 145.(3) ?

