# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_190515a
_database_code_depnum_ccdc_archive 'CCDC 1942384'
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 Br N2 O'
_chemical_formula_weight         314.16

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   3.9930(2)
_cell_length_b                   12.1484(11)
_cell_length_c                   26.691(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.442(2)
_cell_angle_gamma                90
_cell_volume                     1294.35(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1635
_cell_measurement_theta_min      2.268
_cell_measurement_theta_max      25.678

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_F_000             628
_exptl_transmission_factor_min   0.745
_exptl_transmission_factor_max   0.854
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    3.168
_shelx_estimated_absorpt_T_min   0.364
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6312
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.267
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_full        25.014
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2282
_reflns_number_gt                1402
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2282
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0448
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0992
_refine_ls_goodness_of_fit_ref   0.932
_refine_ls_restrained_S_all      0.932
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.45954(13) 0.83969(4) 0.23889(2) 0.0732(2) Uani 1 1 d . . . . .
O1 O 0.0298(8) 0.4955(2) 0.08603(10) 0.0689(9) Uani 1 1 d . . . . .
H1 H 0.067701 0.515607 0.057394 0.103 Uiso 1 1 calc R U . . .
N1 N 0.2794(9) 0.6166(3) 0.01603(12) 0.0560(9) Uani 1 1 d . . . . .
N2 N 0.3832(9) 0.6572(3) -0.02881(12) 0.0543(9) Uani 1 1 d . . . . .
C1 C 0.3260(10) 0.7301(4) 0.19074(14) 0.0547(11) Uani 1 1 d . . . . .
C2 C 0.1743(11) 0.6339(4) 0.20583(16) 0.0627(12) Uani 1 1 d . . . . .
H2 H 0.135897 0.621204 0.239561 0.075 Uiso 1 1 calc R U . . .
C3 C 0.0806(11) 0.5570(4) 0.17019(16) 0.0636(12) Uani 1 1 d . . . . .
H3 H -0.022749 0.492228 0.180162 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1380(11) 0.5745(3) 0.11927(15) 0.0548(11) Uani 1 1 d . . . . .
C5 C 0.2989(10) 0.6711(3) 0.10397(14) 0.0464(10) Uani 1 1 d . . . . .
C6 C 0.3947(10) 0.7476(3) 0.14057(14) 0.0501(10) Uani 1 1 d . . . . .
H6 H 0.506168 0.811362 0.131251 0.060 Uiso 1 1 calc R U . . .
C7 C 0.3729(10) 0.6914(3) 0.05044(14) 0.0470(10) Uani 1 1 d . . . . .
C8 C 0.5307(10) 0.7796(3) 0.02792(14) 0.0501(10) Uani 1 1 d . . . . .
H8 H 0.615105 0.842066 0.043904 0.060 Uiso 1 1 calc R U . . .
C9 C 0.5386(10) 0.7570(3) -0.02266(13) 0.0457(10) Uani 1 1 d . . . . .
C10 C 0.6754(10) 0.8188(3) -0.06511(14) 0.0462(10) Uani 1 1 d . . . . .
C11 C 0.7125(11) 0.7705(4) -0.11189(15) 0.0635(13) Uani 1 1 d . . . . .
H11 H 0.646703 0.697853 -0.117161 0.076 Uiso 1 1 calc R U . . .
C12 C 0.8482(13) 0.8309(4) -0.15088(17) 0.0767(15) Uani 1 1 d . . . . .
H12 H 0.876033 0.797802 -0.181907 0.092 Uiso 1 1 calc R U . . .
C13 C 0.9422(11) 0.9398(4) -0.14394(16) 0.0697(13) Uani 1 1 d . . . . .
H13 H 1.030128 0.980150 -0.170142 0.084 Uiso 1 1 calc R U . . .
C14 C 0.9032(11) 0.9872(4) -0.09749(15) 0.0585(11) Uani 1 1 d . . . . .
H14 H 0.963779 1.060348 -0.092353 0.070 Uiso 1 1 calc R U . . .
C15 C 0.7749(10) 0.9270(3) -0.05866(15) 0.0552(11) Uani 1 1 d . . . . .
H15 H 0.754870 0.959840 -0.027412 0.066 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.916(4) . ?
O1 C4 1.369(5) . ?
N1 C7 1.338(5) . ?
N1 N2 1.368(4) . ?
N2 C9 1.370(5) . ?
C1 C2 1.381(6) . ?
C1 C6 1.390(5) . ?
C2 C3 1.379(6) . ?
C3 C4 1.400(6) . ?
C4 C5 1.404(5) . ?
C5 C6 1.395(5) . ?
C5 C7 1.487(5) . ?
C7 C8 1.387(5) . ?
C8 C9 1.379(5) . ?
C9 C10 1.476(5) . ?
C10 C15 1.382(5) . ?
C10 C11 1.391(5) . ?
C11 C12 1.395(6) . ?
C12 C13 1.386(6) . ?
C13 C14 1.380(6) . ?
C14 C15 1.378(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 105.7(3) . . ?
N1 N2 C9 111.1(3) . . ?
C2 C1 C6 120.6(4) . . ?
C2 C1 Br1 120.6(3) . . ?
C6 C1 Br1 118.8(3) . . ?
C3 C2 C1 119.1(4) . . ?
C2 C3 C4 121.2(4) . . ?
O1 C4 C3 117.8(4) . . ?
O1 C4 C5 122.4(3) . . ?
C3 C4 C5 119.8(4) . . ?
C6 C5 C4 118.2(3) . . ?
C6 C5 C7 120.3(3) . . ?
C4 C5 C7 121.5(4) . . ?
C1 C6 C5 121.0(4) . . ?
N1 C7 C8 110.4(3) . . ?
N1 C7 C5 119.2(3) . . ?
C8 C7 C5 130.4(4) . . ?
C9 C8 C7 107.0(4) . . ?
N2 C9 C8 105.8(3) . . ?
N2 C9 C10 122.3(3) . . ?
C8 C9 C10 131.9(4) . . ?
C15 C10 C11 118.5(4) . . ?
C15 C10 C9 120.0(3) . . ?
C11 C10 C9 121.6(4) . . ?
C10 C11 C12 119.9(4) . . ?
C13 C12 C11 120.8(4) . . ?
C14 C13 C12 118.8(4) . . ?
C15 C14 C13 120.4(4) . . ?
C14 C15 C10 121.5(4) . . ?

_refine_diff_density_max         0.680
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.072



####################################################################### 
# 
# 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_180630h
_database_code_depnum_ccdc_archive 'CCDC 1942385'
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18 O3 S'
_chemical_formula_weight         362.42

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.6861(9)
_cell_length_b                   9.7446(7)
_cell_length_c                   18.3414(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.015(3)
_cell_angle_gamma                90
_cell_volume                     1844.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3058
_cell_measurement_theta_min      2.875
_cell_measurement_theta_max      25.632

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   0.933
_exptl_transmission_factor_max   0.958
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8948
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.875
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_full        25.020
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3243
_reflns_number_gt                2337
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.3697P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3243
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.08609(13) 0.02376(13) 0.12895(8) 0.0411(4) Uani 1 1 d . . . . .
O2 O 0.15888(16) 0.35924(18) 0.24759(9) 0.0637(5) Uani 1 1 d . . . . .
O3 O 0.06693(15) 0.47960(14) 0.12770(9) 0.0553(4) Uani 1 1 d . . . . .
S1 S 0.12423(5) 0.35896(5) 0.16686(3) 0.04180(18) Uani 1 1 d . . . . .
C1 C -0.00609(18) 0.1149(2) 0.17543(11) 0.0379(5) Uani 1 1 d . . . . .
C2 C 0.02103(18) 0.22193(19) 0.13445(11) 0.0345(5) Uani 1 1 d . . . . .
C3 C -0.04618(17) 0.1985(2) 0.05629(11) 0.0343(4) Uani 1 1 d . . . . .
C4 C -0.10952(17) 0.0742(2) 0.05642(11) 0.0354(5) Uani 1 1 d . . . . .
C5 C -0.18526(19) 0.0127(2) -0.00757(12) 0.0446(5) Uani 1 1 d . . . . .
H5 H -0.226224 -0.070936 -0.005784 0.054 Uiso 1 1 calc R U . . .
C6 C -0.1968(2) 0.0826(2) -0.07454(13) 0.0513(6) Uani 1 1 d . . . . .
H6 H -0.247156 0.045265 -0.119222 0.062 Uiso 1 1 calc R U . . .
C7 C -0.1349(2) 0.2077(2) -0.07666(12) 0.0503(6) Uani 1 1 d . . . . .
H7 H -0.144566 0.252007 -0.122686 0.060 Uiso 1 1 calc R U . . .
C8 C -0.05967(19) 0.2669(2) -0.01210(11) 0.0418(5) Uani 1 1 d . . . . .
H8 H -0.018739 0.350537 -0.013971 0.050 Uiso 1 1 calc R U . . .
C9 C 0.0277(2) 0.0787(2) 0.25676(12) 0.0474(5) Uani 1 1 d . . . . .
H9A H 0.105764 0.127529 0.282517 0.057 Uiso 1 1 calc R U . . .
H9B H 0.045802 -0.018826 0.262281 0.057 Uiso 1 1 calc R U . . .
C10 C -0.0798(2) 0.1138(2) 0.29361(12) 0.0493(6) Uani 1 1 d . . . . .
C11 C -0.0845(3) 0.2388(3) 0.32681(16) 0.0788(8) Uani 1 1 d . . . . .
H11 H -0.019241 0.302646 0.328225 0.095 Uiso 1 1 calc R U . . .
C12 C -0.1846(4) 0.2711(4) 0.3581(2) 0.1078(12) Uani 1 1 d . . . . .
H12 H -0.186107 0.356702 0.380228 0.129 Uiso 1 1 calc R U . . .
C13 C -0.2803(4) 0.1811(6) 0.3573(2) 0.1071(14) Uani 1 1 d . . . . .
H13 H -0.347633 0.204059 0.378555 0.128 Uiso 1 1 calc R U . . .
C14 C -0.2774(3) 0.0559(5) 0.3249(2) 0.0999(11) Uani 1 1 d . . . . .
H14 H -0.343066 -0.007158 0.324051 0.120 Uiso 1 1 calc R U . . .
C15 C -0.1771(3) 0.0219(3) 0.29306(15) 0.0749(8) Uani 1 1 d . . . . .
H15 H -0.175864 -0.064030 0.271180 0.090 Uiso 1 1 calc R U . . .
C16 C 0.26291(19) 0.3196(2) 0.13663(12) 0.0420(5) Uani 1 1 d . . . . .
C17 C 0.3491(2) 0.2213(2) 0.17560(15) 0.0600(7) Uani 1 1 d . . . . .
H17 H 0.333043 0.175972 0.216883 0.072 Uiso 1 1 calc R U . . .
C18 C 0.4583(3) 0.1921(3) 0.1521(2) 0.0840(10) Uani 1 1 d . . . . .
H18 H 0.516135 0.126384 0.177935 0.101 Uiso 1 1 calc R U . . .
C19 C 0.4840(3) 0.2585(4) 0.0910(2) 0.0864(10) Uani 1 1 d . . . . .
C20 C 0.3980(3) 0.3548(3) 0.05354(18) 0.0754(8) Uani 1 1 d . . . . .
H20 H 0.414264 0.399784 0.012227 0.090 Uiso 1 1 calc R U . . .
C21 C 0.2874(2) 0.3867(3) 0.07572(14) 0.0540(6) Uani 1 1 d . . . . .
H21 H 0.230135 0.452839 0.049794 0.065 Uiso 1 1 calc R U . . .
C22 C 0.6060(3) 0.2241(5) 0.0664(3) 0.1493(19) Uani 1 1 d . . . . .
H22A H 0.588963 0.147815 0.032112 0.224 Uiso 1 1 calc R U . . .
H22B H 0.674500 0.200605 0.109845 0.224 Uiso 1 1 calc R U . . .
H22C H 0.631305 0.302198 0.041671 0.224 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.367(2) . ?
O1 C4 1.379(2) . ?
O2 S1 1.4302(16) . ?
O3 S1 1.4300(15) . ?
S1 C2 1.7358(19) . ?
S1 C16 1.754(2) . ?
C1 C2 1.360(3) . ?
C1 C9 1.483(3) . ?
C2 C3 1.445(3) . ?
C3 C4 1.388(3) . ?
C3 C8 1.394(3) . ?
C4 C5 1.378(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.515(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.369(4) . ?
C10 C15 1.370(3) . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.345(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.360(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.387(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.377(3) . ?
C16 C17 1.392(3) . ?
C17 C18 1.374(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(4) . ?
C19 C22 1.523(4) . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 107.34(15) . . ?
O3 S1 O2 118.74(10) . . ?
O3 S1 C2 108.00(9) . . ?
O2 S1 C2 109.10(10) . . ?
O3 S1 C16 107.93(10) . . ?
O2 S1 C16 108.32(10) . . ?
C2 S1 C16 103.73(9) . . ?
C2 C1 O1 109.99(17) . . ?
C2 C1 C9 134.97(19) . . ?
O1 C1 C9 115.01(17) . . ?
C1 C2 C3 107.75(17) . . ?
C1 C2 S1 127.45(16) . . ?
C3 C2 S1 124.71(14) . . ?
C4 C3 C8 118.79(18) . . ?
C4 C3 C2 104.66(17) . . ?
C8 C3 C2 136.55(19) . . ?
C5 C4 O1 125.92(18) . . ?
C5 C4 C3 123.84(19) . . ?
O1 C4 C3 110.24(16) . . ?
C4 C5 C6 116.1(2) . . ?
C4 C5 H5 121.9 . . ?
C6 C5 H5 121.9 . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 118.4(2) . . ?
C7 C8 H8 120.8 . . ?
C3 C8 H8 120.8 . . ?
C1 C9 C10 112.32(16) . . ?
C1 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C1 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C15 118.0(2) . . ?
C11 C10 C9 121.2(2) . . ?
C15 C10 C9 120.7(2) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 121.2(4) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.5 . . ?
C14 C13 H13 120.5 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 120.6(3) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C21 C16 C17 120.3(2) . . ?
C21 C16 S1 120.43(17) . . ?
C17 C16 S1 119.29(19) . . ?
C18 C17 C16 119.0(3) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.6(3) . . ?
C20 C19 C22 121.2(4) . . ?
C18 C19 C22 120.2(4) . . ?
C19 C20 C21 121.4(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C20 119.3(2) . . ?
C16 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 C2 0.4(2) . . . . ?
C4 O1 C1 C9 178.75(16) . . . . ?
O1 C1 C2 C3 0.1(2) . . . . ?
C9 C1 C2 C3 -177.7(2) . . . . ?
O1 C1 C2 S1 -176.51(13) . . . . ?
C9 C1 C2 S1 5.6(3) . . . . ?
O3 S1 C2 C1 -142.05(18) . . . . ?
O2 S1 C2 C1 -11.7(2) . . . . ?
C16 S1 C2 C1 103.59(19) . . . . ?
O3 S1 C2 C3 41.83(18) . . . . ?
O2 S1 C2 C3 172.19(16) . . . . ?
C16 S1 C2 C3 -72.53(18) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
S1 C2 C3 C4 176.15(14) . . . . ?
C1 C2 C3 C8 179.4(2) . . . . ?
S1 C2 C3 C8 -3.8(3) . . . . ?
C1 O1 C4 C5 179.67(18) . . . . ?
C1 O1 C4 C3 -0.8(2) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 C5 -179.60(18) . . . . ?
C8 C3 C4 O1 -179.14(16) . . . . ?
C2 C3 C4 O1 0.9(2) . . . . ?
O1 C4 C5 C6 179.13(18) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C6 C7 C8 C3 0.1(3) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
C2 C3 C8 C7 179.7(2) . . . . ?
C2 C1 C9 C10 98.8(3) . . . . ?
O1 C1 C9 C10 -79.0(2) . . . . ?
C1 C9 C10 C11 -90.8(3) . . . . ?
C1 C9 C10 C15 87.6(3) . . . . ?
C15 C10 C11 C12 -0.5(4) . . . . ?
C9 C10 C11 C12 178.0(3) . . . . ?
C10 C11 C12 C13 0.2(5) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
C12 C13 C14 C15 -0.1(5) . . . . ?
C11 C10 C15 C14 0.4(4) . . . . ?
C9 C10 C15 C14 -178.1(2) . . . . ?
C13 C14 C15 C10 -0.2(5) . . . . ?
O3 S1 C16 C21 -10.3(2) . . . . ?
O2 S1 C16 C21 -140.02(18) . . . . ?
C2 S1 C16 C21 104.15(19) . . . . ?
O3 S1 C16 C17 168.73(16) . . . . ?
O2 S1 C16 C17 39.0(2) . . . . ?
C2 S1 C16 C17 -76.85(18) . . . . ?
C21 C16 C17 C18 -0.2(3) . . . . ?
S1 C16 C17 C18 -179.24(19) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C17 C18 C19 C22 179.9(3) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C22 C19 C20 C21 -179.8(3) . . . . ?
C17 C16 C21 C20 0.4(3) . . . . ?
S1 C16 C21 C20 179.35(17) . . . . ?
C19 C20 C21 C16 -0.4(4) . . . . ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_190125a
_database_code_depnum_ccdc_archive 'CCDC 1942386'
_audit_update_record             
;
2019-07-22 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H20 N2 O3 S'
_chemical_formula_weight         392.46

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   20.9823(17)
_cell_length_b                   5.1771(3)
_cell_length_c                   18.9441(15)
_cell_angle_alpha                90
_cell_angle_beta                 105.594(3)
_cell_angle_gamma                90
_cell_volume                     1982.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    768
_cell_measurement_theta_min      2.184
_cell_measurement_theta_max      25.914

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   0.853
_exptl_transmission_factor_max   0.936
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.659
_shelx_estimated_absorpt_T_min   0.579
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6252
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.375
_diffrn_reflns_theta_max         66.046
_diffrn_reflns_theta_full        66.046
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3449
_reflns_number_gt                2001
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.00194(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3449
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.33818(13) 0.6252(5) 0.47263(14) 0.0480(7) Uani 1 1 d . . . . .
H1 H 0.350762 0.460031 0.470062 0.058 Uiso 1 1 d R U . . .
N2 N 0.27321(12) 0.6587(5) 0.42490(13) 0.0454(7) Uani 1 1 d . . . . .
H2A H 0.259953 0.510411 0.400609 0.055 Uiso 1 1 d R U . . .
O1 O 0.22203(11) 1.1350(4) 0.36442(12) 0.0602(7) Uani 1 1 d . . . . .
H1A H 0.252830 1.059535 0.392796 0.090 Uiso 1 1 calc R U . . .
O2 O 0.45378(11) 0.7589(5) 0.50278(13) 0.0651(7) Uani 1 1 d . . . . .
O3 O 0.36440(11) 1.0697(4) 0.44527(13) 0.0600(7) Uani 1 1 d . . . . .
S1 S 0.39283(4) 0.81547(16) 0.45033(5) 0.0507(3) Uani 1 1 d . . . . .
C1 C 0.22551(16) 0.7288(6) 0.46737(18) 0.0474(8) Uani 1 1 d . . . . .
H1B H 0.243662 0.879251 0.497476 0.057 Uiso 1 1 calc R U . . .
C2 C 0.16171(17) 0.8146(6) 0.41297(17) 0.0473(8) Uani 1 1 d . . . . .
C3 C 0.16315(18) 1.0210(6) 0.36626(19) 0.0507(9) Uani 1 1 d . . . . .
C4 C 0.10566(19) 1.1228(7) 0.32107(19) 0.0594(10) Uani 1 1 d . . . . .
H4 H 0.107350 1.264713 0.291524 0.071 Uiso 1 1 calc R U . . .
C5 C 0.0458(2) 1.0117(8) 0.3203(2) 0.0690(11) Uani 1 1 d . . . . .
H5 H 0.006917 1.078221 0.289899 0.083 Uiso 1 1 calc R U . . .
C6 C 0.04344(19) 0.8031(8) 0.3643(2) 0.0679(11) Uani 1 1 d . . . . .
H6 H 0.002999 0.727005 0.363037 0.081 Uiso 1 1 calc R U . . .
C7 C 0.10098(18) 0.7064(7) 0.4103(2) 0.0615(10) Uani 1 1 d . . . . .
H7 H 0.098825 0.565787 0.440152 0.074 Uiso 1 1 calc R U . . .
C8 C 0.21529(17) 0.5245(7) 0.51753(19) 0.0545(9) Uani 1 1 d . . . . .
C9 C 0.20173(18) 0.3680(7) 0.5559(2) 0.0566(10) Uani 1 1 d . . . . .
C10 C 0.17949(19) 0.1748(7) 0.5984(2) 0.0546(9) Uani 1 1 d . . . . .
C11 C 0.1200(2) 0.0517(8) 0.5686(2) 0.0698(12) Uani 1 1 d . . . . .
H11 H 0.094940 0.096751 0.521880 0.084 Uiso 1 1 calc R U . . .
C12 C 0.0968(2) -0.1375(9) 0.6071(3) 0.0882(14) Uani 1 1 d . . . . .
H12 H 0.056662 -0.218687 0.586210 0.106 Uiso 1 1 calc R U . . .
C13 C 0.1327(3) -0.2032(10) 0.6747(3) 0.0978(17) Uani 1 1 d . . . . .
H13 H 0.117462 -0.332040 0.700241 0.117 Uiso 1 1 calc R U . . .
C14 C 0.1915(3) -0.0826(10) 0.7063(3) 0.0961(16) Uani 1 1 d . . . . .
H14 H 0.215414 -0.127338 0.753583 0.115 Uiso 1 1 calc R U . . .
C15 C 0.2158(2) 0.1078(8) 0.6680(2) 0.0805(13) Uani 1 1 d . . . . .
H15 H 0.255969 0.188299 0.689236 0.097 Uiso 1 1 calc R U . . .
C16 C 0.39802(15) 0.7278(6) 0.36283(18) 0.0480(9) Uani 1 1 d . . . . .
C17 C 0.36062(18) 0.8514(7) 0.3010(2) 0.0667(11) Uani 1 1 d . . . . .
H17 H 0.333951 0.990953 0.305168 0.080 Uiso 1 1 calc R U . . .
C18 C 0.3632(2) 0.7655(8) 0.2327(2) 0.0769(12) Uani 1 1 d . . . . .
H18 H 0.337686 0.848819 0.191225 0.092 Uiso 1 1 calc R U . . .
C19 C 0.4020(2) 0.5628(8) 0.2242(2) 0.0682(11) Uani 1 1 d . . . . .
C20 C 0.4392(2) 0.4436(8) 0.2861(2) 0.0714(12) Uani 1 1 d . . . . .
H20 H 0.466060 0.305214 0.281462 0.086 Uiso 1 1 calc R U . . .
C21 C 0.43797(17) 0.5236(7) 0.3556(2) 0.0609(10) Uani 1 1 d . . . . .
H21 H 0.463845 0.440317 0.396914 0.073 Uiso 1 1 calc R U . . .
C22 C 0.4024(2) 0.4683(10) 0.1485(2) 0.1056(17) Uani 1 1 d . . . . .
H22A H 0.373613 0.574619 0.111986 0.158 Uiso 1 1 calc R U . . .
H22B H 0.446595 0.478032 0.143165 0.158 Uiso 1 1 calc R U . . .
H22C H 0.387348 0.292594 0.142403 0.158 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.430(3) . ?
N1 S1 1.651(3) . ?
N1 H1 0.9000 . ?
N2 C1 1.488(4) . ?
N2 H2A 0.9000 . ?
O1 C3 1.378(4) . ?
O1 H1A 0.8200 . ?
O2 S1 1.423(2) . ?
O3 S1 1.438(2) . ?
S1 C16 1.750(3) . ?
C1 C8 1.476(5) . ?
C1 C2 1.520(4) . ?
C1 H1B 0.9800 . ?
C2 C7 1.380(4) . ?
C2 C3 1.393(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.377(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.380(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.173(4) . ?
C9 C10 1.439(5) . ?
C10 C15 1.377(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.384(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.343(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.369(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.399(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C21 1.379(4) . ?
C16 C17 1.380(4) . ?
C17 C18 1.382(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(5) . ?
C19 C22 1.517(5) . ?
C20 C21 1.387(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 S1 112.06(18) . . ?
N2 N1 H1 109.0 . . ?
S1 N1 H1 108.6 . . ?
N1 N2 C1 110.7(2) . . ?
N1 N2 H2A 109.3 . . ?
C1 N2 H2A 108.9 . . ?
C3 O1 H1A 109.5 . . ?
O2 S1 O3 120.93(15) . . ?
O2 S1 N1 104.72(14) . . ?
O3 S1 N1 105.01(14) . . ?
O2 S1 C16 109.56(16) . . ?
O3 S1 C16 107.75(16) . . ?
N1 S1 C16 108.18(14) . . ?
C8 C1 N2 114.1(3) . . ?
C8 C1 C2 113.1(3) . . ?
N2 C1 C2 107.6(3) . . ?
C8 C1 H1B 107.2 . . ?
N2 C1 H1B 107.2 . . ?
C2 C1 H1B 107.2 . . ?
C7 C2 C3 117.8(3) . . ?
C7 C2 C1 122.8(3) . . ?
C3 C2 C1 119.3(3) . . ?
O1 C3 C4 117.4(3) . . ?
O1 C3 C2 121.2(3) . . ?
C4 C3 C2 121.4(3) . . ?
C5 C4 C3 119.2(4) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C5 C4 120.3(4) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 120.0(4) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 121.2(4) . . ?
C2 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C1 174.4(4) . . ?
C8 C9 C10 175.0(4) . . ?
C15 C10 C11 118.8(4) . . ?
C15 C10 C9 122.1(4) . . ?
C11 C10 C9 119.1(3) . . ?
C10 C11 C12 121.2(4) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 119.7(5) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C12 C13 C14 120.7(5) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C15 120.3(5) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C10 C15 C14 119.3(4) . . ?
C10 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C21 C16 C17 119.6(3) . . ?
C21 C16 S1 119.2(3) . . ?
C17 C16 S1 121.2(3) . . ?
C16 C17 C18 119.2(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C19 C18 C17 122.3(4) . . ?
C19 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C20 C19 C18 117.8(4) . . ?
C20 C19 C22 121.2(4) . . ?
C18 C19 C22 121.0(4) . . ?
C19 C20 C21 121.8(4) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C16 C21 C20 119.4(4) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 N2 C1 -123.2(2) . . . . ?
N2 N1 S1 O2 179.73(19) . . . . ?
N2 N1 S1 O3 51.4(2) . . . . ?
N2 N1 S1 C16 -63.5(2) . . . . ?
N1 N2 C1 C8 -65.1(3) . . . . ?
N1 N2 C1 C2 168.6(2) . . . . ?
C8 C1 C2 C7 -1.4(5) . . . . ?
N2 C1 C2 C7 125.6(3) . . . . ?
C8 C1 C2 C3 174.8(3) . . . . ?
N2 C1 C2 C3 -58.2(4) . . . . ?
C7 C2 C3 O1 -178.4(3) . . . . ?
C1 C2 C3 O1 5.2(4) . . . . ?
C7 C2 C3 C4 2.9(5) . . . . ?
C1 C2 C3 C4 -173.4(3) . . . . ?
O1 C3 C4 C5 178.9(3) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 C7 1.0(6) . . . . ?
C3 C2 C7 C6 -1.5(5) . . . . ?
C1 C2 C7 C6 174.7(3) . . . . ?
C5 C6 C7 C2 -0.4(6) . . . . ?
C15 C10 C11 C12 -0.6(6) . . . . ?
C9 C10 C11 C12 179.2(3) . . . . ?
C10 C11 C12 C13 0.1(6) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
C12 C13 C14 C15 -1.3(8) . . . . ?
C11 C10 C15 C14 0.1(6) . . . . ?
C9 C10 C15 C14 -179.7(3) . . . . ?
C13 C14 C15 C10 0.8(7) . . . . ?
O2 S1 C16 C21 30.6(3) . . . . ?
O3 S1 C16 C21 164.0(3) . . . . ?
N1 S1 C16 C21 -83.0(3) . . . . ?
O2 S1 C16 C17 -152.4(3) . . . . ?
O3 S1 C16 C17 -19.0(3) . . . . ?
N1 S1 C16 C17 94.0(3) . . . . ?
C21 C16 C17 C18 0.9(5) . . . . ?
S1 C16 C17 C18 -176.1(3) . . . . ?
C16 C17 C18 C19 -0.4(6) . . . . ?
C17 C18 C19 C20 -0.1(6) . . . . ?
C17 C18 C19 C22 178.3(4) . . . . ?
C18 C19 C20 C21 0.1(6) . . . . ?
C22 C19 C20 C21 -178.3(4) . . . . ?
C17 C16 C21 C20 -0.9(5) . . . . ?
S1 C16 C21 C20 176.2(3) . . . . ?
C19 C20 C21 C16 0.3(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.90 2.11 2.999(3) 168.7 1_545 yes
N2 H2A O1 0.90 2.14 3.026(3) 167.2 1_545 yes
O1 H1A N2 0.82 2.17 2.808(3) 134.4 . yes
O1 H1A O3 0.82 2.28 2.987(3) 144.0 . yes
C21 H21 O2 0.93 2.43 3.349(4) 170.8 3_666 yes

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048



